Tetrazolinone compound and applications thereof

Abstract

The compound represented by formula (1): ##STR00001##
wherein R.sup.4 and R.sup.5 each represents a hydrogen atom, a halogen atom, or a C1-C3 alkyl group; R.sup.6 represents a C1-C4 alkyl group, a C3-C6 cycloalkyl group, or the like; R.sup.7, R.sup.8, and R.sup.9 each represents a hydrogen atom, a halogen atom, or the like; R.sup.10 represents a C1-C3 alkyl group, or the like; R.sup.13 represents a C1-C3 alkyl group, or the like; and Q represents a phenyl group, or the like; has an excellent control effect on pests.

Claims

1. A tetrazolinone compound represented by formula (1): ##STR00615## wherein, R.sup.4, R.sup.5, R.sup.7, R.sup.8, and R.sup.9 are hydrogen atoms; R.sup.10 is a methyl group; X is an oxygen atom; R.sup.6 is a C1-C3 alkyl group optionally having one or more halogen atoms, a C3-C4 cycloalkyl group optionally having one or more halogen atoms, a C1-C3 alkoxy group optionally having one or more halogen atoms, a halogen atom, a C2-C3 alkenyl group, a C2-C3 alkynyl group, or a C1-C3 alkylthio group; and either (a) R13 is methyl; and Q is the following structure ##STR00616## wherein, R.sup.1, R.sup.3, R.sup.11 and R.sup.12 each represent a hydrogen atom and R.sup.2 is CF.sub.3; or (b) R.sup.13 is a C1-C4 alkyl group, a C3-C4 cycloalkyl group, a hydrogen atom, a C2-C4 alkenyl group, a C2-C4 alkynyl group, a C1-C4 alkoxy group, or a C1-C4 alkylthio group; and Q is the following structure: ##STR00617## wherein, R.sup.3, R.sup.11, and R.sup.12 each represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a C1-C3 alkoxy group optionally having one or more halogen atoms, a C1-C3 alkylthio group optionally having one or more halogen atoms, a C1-C3 alkyl group optionally having one or more halogen atoms, or a C3-C4 cycloalkyl group optionally having one or more halogen atoms; R.sup.1 and R.sup.2 form a four-membered ring or a five-membered ring together with the carbon atom to which they are attached; and the ring may contain one or more atoms selected from the group consisting of an oxygen atom, a sulfur atom, and a nitrogen atom as a ring-constituent atom, and may have an oxo group, a thioxo group, or a C1-C3 alkoxyimino group on the same carbon atom, and may have one or two oxide groups on the same sulfur atom; and the phenyl moiety and the ring may have one or more atoms or groups selected from Group P.sup.4 and, when the number of atoms or groups selected from Group P.sup.4 is two or more, the atoms or groups may be the same or different; and the symbol ∘ represents a binding site; and Group P.sup.4 consisting of a halogen atom, a cyano group, a nitro group, a C1-C4 alkyl group, a C3-C6 cycloalkyl group, a C1-C4 haloalkyl group, a C3-C6 halocycloalkyl group, a C1-C4 alkoxy group, a C1-C4 haloalkoxy group, a C1-C4 alkylthio group, and a C1-C4 haloalkylthio group.

2. The tetrazolinone compound according to claim 1, wherein R.sup.6 is C1-C3 alkyl group, a C3-C4 cycloalkyl group, a C1-C3 haloalkyl group, a halogen atom, or a methoxy group; R.sup.13 is a C1-C3 alkyl group; R.sup.1 and R.sup.2 are bonded to form -E-CH.sub.2—CH.sub.2— (provided that E is bonded with the carbon atom to which R.sup.2 is attached, and represents CH.sub.2 or an oxygen atom); and R.sup.3, R.sup.11, and R.sup.12 each represents a hydrogen atom, a halogen atom, a C1-C3 alkyl group optionally having one or more halogen atoms, or a C1-C3 alkoxy group optionally having one or more halogen atoms.

3. A pest control agent comprising the tetrazolinone compound according to claim 1 as an active ingredient.

4. A method for controlling pests, which comprises treating the plant body or a cultivation area of the plant with an effective amount of the tetrazolinone compound according to claim 1.

5. The tetrazolinone compound according to claim 1, which is 1-{3-methyl-2-[1-(3-trifluoromethylphenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one.

Description

EXAMPLES

(1) The present invention will be more specifically described below by way of Examples such as Production Examples, Formulation Examples, and Test Examples, but the present invention is not limited only to these Examples.

(2) In the following Production Examples of the present compounds, an intermediate produced in the following Reference Production Example is mentioned as C4A (numeric portion means the number of Reference Production Example. In this case, this means an intermediate produced in Reference Production Example 4).

(3) First, Production Examples will be shown.

Production Example 1

(4) A mixture of 0.59 g of C2A, 0.38 g of C55A, 0.35 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1-{3-chloro-2-[1-(3-difluoromethylphenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 1).

(5) ##STR00119##

(6) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.71 (1H, s), 7.65 (1H, d, J=7.2 Hz), 7.60 (1H, d, J=7.2 Hz), 7.51-7.41 (3H, m), 7.33 (1H, d, J=7.2 Hz), 6.67 (1H, t, J=56.3 Hz), 5.46 (2H, s), 3.61 (3H, s), 2.10 (3H, s).

Production Example 2

(7) A mixture of 0.52 g of C11A, 0.34 g of C55A, 0.31 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1-{3-methyl-2-[1-(3-difluoromethylphenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 2).

(8) ##STR00120##

(9) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.74 (1H, s), 7.66 (1H, d, J=7.8 Hz), 7.49 (1H, d, J=7.8 Hz), 7.45-7.38 (3H, m), 7.23 (1H, t, J=4.6 Hz), 6.67 (1H, t, J=56.3 Hz), 5.26 (2H, s), 3.65 (3H, s), 2.55 (3H, s), 2.13 (3H, s).

Production Example 3

(10) A mixture of 0.40 g of C2A, 0.25 g of C40A, 0.24 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1-[2-(1-benzo[1,3]dioxan-5-yl-ethylideneaminooxymethyl)-3-chlorophenyl]-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 3).

(11) ##STR00121##

(12) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.58 (1H, dd, J=8.1, 1.5 Hz), 7.41 (1H, t, J=8.1 Hz), 7.32 (1H, dd, J=7.9, 1.3 Hz), 7.11 (1H, d, J=1.7 Hz), 7.00 (1H, dd, J=8.2, 1.8 Hz), 6.75 (1H, d, J=8.3 Hz), 5.96 (2H, s), 5.43 (2H, s), 3.63 (3H, s), 2.03 (3H, s).

Production Example 4

(13) A mixture of 0.40 g of C2A, 0.22 g of C20A, 0.24 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 3-{1-[2-chloro-6-(4-methyl-5-oxo-4,5-dihydrotetrazol-1-yl)benzyloxyimino]ethyl}benzonitrile (hereinafter referred to as the present compound 4).

(14) ##STR00122##

(15) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.9 (1H, t, J=1.5 Hz), 7.78 (1H, dq, J=8.1, 1.0 Hz), 7.61 (2H, dt, J=7.9, 1.3 Hz), 7.44 (2H, t, J=8.1 Hz), 7.34 (1H, dd, J=7.8, 1.2 Hz), 5.46 (2H, s), 3.67 (3H, s), 2.09 (3H, s).

Production Example 5

(16) A mixture of 0.40 g of C2A, 0.22 g of C21A, 0.24 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1-{3-chloro-2-[1-(3-methoxyphenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 5).

(17) ##STR00123##

(18) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.59 (1H, dd, J=8.2 1.3 Hz), 7.42 (1H, t, J=8.1 Hz), 7.32 (1H, dd, J=8.1, 1.2 Hz), 7.23 (1H, d, J=8.1 Hz), 7.14-7.10 (2H, m), 6.88 (1H, dq, J=8.2, 1.2 Hz), 5.46 (2H, s), 3.83 (3H, s), 3.59 (3H, s), 2.07 (3H, s).

Production Example 6

(19) A mixture of 0.40 g of C2A, 0.23 g of C22A, 0.24 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1-{3-chloro-2-[1-(3-nitrophenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 6).

(20) ##STR00124##

(21) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.39 (1H, t, J=1.9 Hz), 8.19 (1H, d, J=8.2 Hz), 7.91 (1H, d, J=7.7 Hz), 7.61 (1H, d, J=8.0 Hz), 7.51 (1H, t, J=8.0 Hz), 7.44 (1H, t, J=8.1 Hz), 7.34 (1H, d, J=8.0 Hz), 5.48 (2H, s), 3.67 (3H, s), 2.14 (3H, s).

Production Example 7

(22) A mixture of 0.40 g of C11A, 0.30 g of C42A, 0.24 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1-{3-methyl-2-[1-(3-tri fluoromethylphenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 7).

(23) ##STR00125##

(24) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.84 (1H, s), 7.75 (1H, d, J=7.8 Hz), 7.58 (1H, d, J=7.8 Hz), 7.46 (1H, t, J=7.8 Hz), 7.38 (2H, m), 7.23 (1H, t, J=4.6 Hz), 5.27 (2H, s), 3.66 (3H, s), 2.56 (3H, s), 2.13 (3H, s).

Production Example 8

(25) A mixture of 0.40 g of C2A, 0.30 g of C56A, 0.24 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1-{3-chloro-2-[1-(2,2-difluorobenzo[1,3]dioxoyl-5yl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 8).

(26) ##STR00126##

(27) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.60 (1H, dd, J=8.2, 1.3 Hz), 7.43 (1H, t, J=8.1 Hz), 7.35-7.32 (2H, m), 7.24 (1H, dd, J=8.5, 1.7 Hz), 7.00 (1H, d, J=8.3 Hz), 5.44 (2H, s), 3.65 (3H, s), 2.06 (3H, s).

Production Example 9

(28) A mixture of 0.40 g of C2A, 0.35 g of C57A, 0.24 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1-(3-chloro-2-{1-[3-(1,1,2,2-tetrafluoroethoxyl)phenyl]ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 9).

(29) ##STR00127##

(30) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.60 (1H, dd, J=8.1, 1.2 Hz), 7.48-7.41 (3H, m), 7.36-7.32 (2H, m), 7.19 (1H, dq, J=8.2, 1.1 Hz), 5.93 (1H, tt, J=53.1, 2.9 Hz), 5.46 (2H, s), 3.61 (3H, s), 2.08 (3H, s).

Production Example 10

(31) A mixture of 0.40 g of C2A, 0.23 g of C23A, 0.24 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1-{3-chloro-2-[1-(3,5-dimethylphenyl)ethylideneaminooxymethyl]phen yl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 10).

(32) ##STR00128##

(33) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.58 (1H, dd, J=8.1, 1.0 Hz), 7.41 (1H, t, J=8.1 Hz), 7.32 (1H, d, J=7.6 Hz), 7.16 (2H, s), 6.97 (1H, s), 5.45 (2H, s), 3.58 (3H, s), 2.31 (6H, s), 2.05 (3H, s).

Production Example 11

(34) A mixture of 0.40 g of C2A, 0.28 g of C58A, 0.24 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1-{3-chloro-2-[1-(3-difluoromethoxyphenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 11).

(35) ##STR00129##

(36) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.59 (1H, dd, J=8.2, 1.3 Hz), 7.43 (1H, t, J=8.1 Hz), 7.38-7.30 (4H, m), 7.09 (1H, d, J=8.5 Hz), 6.58 (1H, t, J=73.9 Hz), 5.44 (2H, s), 3.63 (3H, s), 2.08 (3H, s).

Production Example 12

(37) A mixture of 0.30 g of C8A, 0.21 g of C42A, 0.23 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1-{3-methoxy-2-[1-(3-trifluoromethylphenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 12).

(38) ##STR00130##

(39) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.82 (1H, s), 7.73 (1H, d, J=7.8 Hz), 7.58 (1H, d, J=7.8 Hz), 7.45 (2H, m), 7.09 (1H, d, J=8.5 Hz), 7.01 (1H, d, J=8.1 Hz), 5.40 (2H, s), 3.93 (3H, s), 3.59 (3H, s), 2.08 (3H, s).

Production Example 13

(40) A mixture of 0.40 g of C2A, 0.20 g of C24A, 0.24 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1-[3-chloro-2-(indan-1-ylideneaminooxymethyl]phenyl)-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 13).

(41) ##STR00131##

(42) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.60-7.56 (2H, m), 7.41 (1H, t, J=8.1 Hz), 7.33-7.20 (4H, m), 5.41 (2H, s), 3.64 (3H, s), 2.97-2.94 (2H, m), 2.74-2.71 (2H, m).

Production Example 14

(43) A mixture of 0.40 g of C2A, 0.22 g of C25A, 0.24 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1-[3-chloro-2-(6-methylindan-1-ylideneaminooxymethyl]phenyl)-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 14).

(44) ##STR00132##

(45) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.58 (1H, dd, J=8.1, 1.2 Hz), 7.41 (2H, t, J=8.1 Hz), 7.32 (1H, dd, J=7.8, 1.2 Hz), 7.16-7.11 (2H, m), 5.41 (2H, s), 3.65 (3H, s), 2.92-2.89 (2H, m), 2.73-2.70 (2H, m), 2.35 (3H, s).

Production Example 15

(46) A mixture of 0.40 g of C2A, 0.26 g of C26A, 0.24 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1-{3-chloro-2-[1-(naphthalen-2-yl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 15).

(47) ##STR00133##

(48) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.94 (1H, s), 7.86-7.77 (4H, m), 7.61 (1H, d, J=8.2 Hz), 7.49-7.41 (3H, m), 7.35 (1H, d, J=8.0 Hz), 5.52 (2H, s), 3.57 (3H, s), 2.20 (3H, s).

Production Example 16

(49) A mixture of 0.40 g of C2A, 0.24 g of C28A, 0.24 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1-{3-chloro-2-[1-(3-chlorophenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 16).

(50) ##STR00134##

(51) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.59 (1H, dd, J=8.2, 1.3 Hz), 7.55 (1H, t, J=1.7 Hz), 7.45-7.41 (2H, m), 7.34-7.24 (3H, m), 5.46 (2H, s), 3.62 (3H, s), 2.06 (3H, s).

Production Example 17

(52) A mixture of 0.40 g of C2A, 0.21 g of C46A, 0.24 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1-{3-chloro-2-[1-(3-methylphenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 17).

(53) ##STR00135##

(54) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.59 (1H, dd, J=8.1, 1.2 Hz), 7.42 (1H, t, J=8.1 Hz), 7.38-7.32 (3H, m), 7.22 (1H, t, J=7.7 Hz), 7.15 (1H, d, J=7.3 Hz), 5.46 (2H, s), 3.58 (3H, s), 2.36 (3H, s), 2.07 (3H, s).

Production Example 18

(55) A mixture of 0.40 g of C2A, 0.28 g of C29A, 0.24 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1-{3-chloro-2-[1-(2-trifluoromethylphenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 18).

(56) ##STR00136##

(57) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.65 (1H, d, J=7.8 Hz), 7.58 (1H, dd, J=8.1, 1.2 Hz), 7.53 (1H, t, J=7.2 Hz), 7.47-7.41 (2H, m), 7.34 (1H, dd, J=7.8, 3.9 Hz), 7.28-7.25 (1H, m), 5.43 (2H, s), 3.59 (3H, s), 2.02 (3H, s).

Production Example 19

(58) A mixture of 0.40 g of C2A, 0.24 g of C30A, 0.24 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1-{3-chloro-2-[1-(indan-5-yl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 19).

(59) ##STR00137##

(60) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.58 (1H, dt, J=8.1, 1.2 Hz), 7.43-7.39 (2H, m), 7.33-7.30 (2H, m), 7.17 (1H, d, J=8.0 Hz), 5.45 (2H, s), 3.59 (3H, s), 2.89 (4H, m), 2.17 (3H, s), 2.08-2.04 (2H, m).

Production Example 20

(61) A mixture of 0.40 g of C2A, 0.28 g of C31A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1-{3-chloro-2-[1-(3,5-dichlorophenyl)ethylideneaminooxymethyl]phen yl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 20).

(62) ##STR00138##

(63) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.60 (1H, d, J=8.1 Hz), 7.46-7.42 (3H, m), 7.34-7.31 (2H, m), 5.45 (2H, s), 3.66 (3H, s), 2.04 (3H, s).

Production Example 21

(64) A mixture of 0.40 g of C2A, 0.25 g of C32A, 0.24 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1-[3-chloro-2-(6-chloroindan-1-ylideneaminooxymethyl]phenyl)-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 21).

(65) ##STR00139##

(66) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.59 (1H, dd, J=8.2, 1.3 Hz), 7.55 (1H, d, J=2.0 Hz), 7.42 (1H, t, J=8.1 Hz), 7.33 (1H, dd, J=8.1, 1.2 Hz), 7.24 (1H, d, J=2.2 Hz), 7.17 (1H, d, J=8.1 Hz), 5.41 (2H, s), 3.69 (3H, s), 2.94-2.90 (2H, m), 2.75-2.72 (2H, m).

Production Example 22

(67) A mixture of 0.40 g of C2A, 0.37 g of C33A, 0.24 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1-{3-chloro-2-[1-(3,5-ditrifluoromethylphenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 22).

(68) ##STR00140##

(69) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.00 (2H, s), 7.83 (1H, s), 7.61 (1H, dd, J=8.3, 1.2 Hz), 7.45 (1H, t, J=8.1 Hz), 7.33 (1H, dd, J=8.1, 1.2 Hz), 5.46 (2H, s), 3.67 (3H, s), 2.14 (3H, s).

Production Example 23

(70) A mixture of 0.40 g of C2A, 0.27 g of C42A, 0.24 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1-{3-chloro-2-[1-(3-trifluoromethylphenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 23).

(71) ##STR00141##

(72) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.81 (1H, s), 7.74 (1H, d, J=7.8 Hz), 7.61-7.58 (2H, m), 7.47-7.41 (2H, m), 7.33 (1H, dd, J=8.1, 1.2 Hz), 5.47 (2H, s), 3.62 (3H, s), 2.11 (3H, s).

Production Example 24

(73) A mixture of 0.40 g of C2A, 0.19 g of acetophenone oxime, 0.24 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated.

(74) The obtained residue was subjected to silica gel column chromatography to obtain 1-[3-chloro-2-(1-phenylethylideneaminooxymethyl)phenyl]-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 24).

(75) ##STR00142##

(76) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.66 (2H, d, J=8.5 Hz), 7.59 (3H, t, J=7.6 Hz), 7.43 (1H, t, J=8.1 Hz), 7.33 (2H, d, J=7.3 Hz), 5.47 (2H, s), 3.62 (3H, s), 2.10 (3H, s).

Production Example 25

(77) A mixture of 0.40 g of C2A, 0.30 g of C34A, 0.24 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1-{3-chloro-2-[1-(3-trifluoromethoxyphenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 25).

(78) ##STR00143##

(79) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.60 (1H, d, J=8.2 Hz), 7.49-7.41 (3H, m), 7.38-7.32 (2H, m), 7.19 (1H, d, J=8.2 Hz), 5.46 (2H, s), 3.62 (3H, s), 2.08 (3H, s).

Production Example 26

(80) A mixture of 0.40 g of C2A, 0.26 g of C35A, 0.24 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1-[3-chloro-2-(2,2,2-trifluoro-1-phenylethylideneaminooxymethyl)phenyl]-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 26).

(81) ##STR00144##

(82) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.58 (1H, dd, J=8.1, 1.2 Hz), 7.47-7.34 (7H, m), 5.53 (2H, s), 3.59 (3H, s).

Production Example 27

(83) A mixture of 0.40 g of C2A, 0.28 g of C36A, 0.24 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1-{3-chloro-2-[1-(4-trifluoromethylphenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 27).

(84) ##STR00145##

(85) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.66 (2H, d, J=8.3 Hz), 7.61-7.57 (3H, m), 7.44 (1H, t, J=8.1 Hz), 7.33 (1H, d, J=7.8 Hz), 5.47 (2H, s), 3.62 (3H, s), 2.10 (3H, s).

Production Example 28

(86) A mixture of 0.40 g of C2A, 0.24 g of C37A, 0.24 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1-{3-chloro-2-[1-(3,5-difluorophenyl)ethylideneaminooxymethyl]phen yl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 28).

(87) ##STR00146##

(88) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.60 (1H, dd, J=8.1, 1.2 Hz), 7.43 (1H, t, J=8.1 Hz), 7.33 (1H, dd, J=7.8, 1.2 Hz), 7.08 (2H, dd, J=8.8, 2.2 Hz), 6.77 (1H, tt, J=8.8, 2.4 Hz), 5.46 (2H, s), 3.66 (3H, s), 2.04 (3H, s).

Production Example 29

(89) A mixture of 0.30 g of C17A, 0.21 g of C42A, 0.17 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.34 g of 1-{3-cyclopropyl-2-[1-(3-trifluoromethylphenyl)ethylideneaminooxym ethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 29).

(90) ##STR00147##

(91) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.84 (1H, s), 7.75 (1H, d, J=7.7 Hz), 7.58 (1H, d, J=7.7 Hz), 7.46 (1H, t, J=7.9 Hz), 7.39 (1H, t, J=7.9 Hz), 7.27-7.21 (2H, m), 5.50 (2H, s), 3.64 (3H, s), 2.27-2.20 (1H, m), 2.12 (3H, s), 1.08-1.03 (2H, m), 0.81-0.77 (2H, m).

Production Example 30

(92) A mixture of 0.30 g of C14A, 0.22 g of C42A, 0.18 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.35 g of 1-{3-ethyl-2-[1-(3-trifluoromethylphenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 30).

(93) ##STR00148##

(94) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.84 (1H, s), 7.75 (1H, d, J=8.0 Hz), 7.59 (1H, d, J=7.7 Hz), 7.47 (1H, d, J=8.0 Hz), 7.44-7.41 (2H, m), 7.23 (1H, dd, J=6.0, 3.4 Hz), 5.30 (2H, s), 3.63 (3H, s), 2.91 (2H, q, J=7.6 Hz), 2.12 (3H, s), 1.31 (3H, t, J=7.5 Hz).

Production Example 31

(95) A mixture of 0.56 g of C11A, 0.34 g of C28A, 0.36 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.50 g of 1-{3-methyl-2-[1-(3-chlorophenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 31).

(96) ##STR00149##

(97) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.58 (1H, t, J=1.8 Hz), 7.44 (1H, dt, J=7.3, 1.6 Hz), 7.39-7.38 (2H, m), 7.32-7.28 (2H, m), 7.25-7.21 (1H, m), 5.26 (2H, s), 3.66 (3H, s), 2.55 (3H, s), 2.08 (3H, s).

Production Example 32

(98) A mixture of 0.56 g of C11A, 0.44 g of C34A, 0.36 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.60 g of 1-{3-methyl-2-[1-(3-trifluoromethoxyphenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 32).

(99) ##STR00150##

(100) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.51-7.45 (2H, m), 7.39-7.34 (3H, m), 7.25-7.17 (2H, m), 5.26 (2H, s), 3.66 (3H, s), 2.55 (3H, s), 2.10 (3H, s).

Production Example 33

(101) A mixture of 0.56 g of C11A, 0.50 g of C57A, 0.36 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.65 g of 1-(3-methyl-2-{1-[3-(1,1,2,2-tetrafluoroethoxyl)phenyl]ethylideneaminooxymethyl}phenyl)-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 33).

(102) ##STR00151##

(103) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.48 (1H, dt, J=7.8, 1.3 Hz), 7.44 (1H, s), 7.38-7.32 (3H, m), 7.24-7.17 (2H, m), 5.93 (1H, tt, J=53.1, 2.9 Hz), 5.26 (2H, s), 3.65 (3H, s), 2.55 (3H, s), 2.10 (3H, s).

Production Example 34

(104) A mixture of 0.56 g of C11A, 0.33 g of C21A, 0.36 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.36 g of 1-{3-methyl-2-[1-(3-methoxyphenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 34).

(105) ##STR00152##

(106) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.37-7.35 (2H, m), 7.26-7.20 (2H, m), 7.16-7.12 (2H, m), 6.88 (1H, dd, J=8.2, 2.6 Hz), 5.25 (2H, s), 3.82 (3H, s), 3.63 (3H, s), 2.54 (3H, s), 2.09 (3H, s).

Production Example 35

(107) A mixture of 0.56 g of C11A, 0.35 g of C30A, 0.36 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.24 g of 1-{3-methyl-2-[1-(indan-5-yl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 35).

(108) ##STR00153##

(109) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.45 (1H, s), 7.36-7.32 (3H, m), 7.25-7.16 (2H, m), 5.24 (2H, s), 3.63 (3H, s), 2.92-2.86 (4H, m), 2.54 (3H, s), 2.09 (3H, s), 2.09-2.02 (2H, m).

Production Example 36

(110) A mixture of 0.56 g of C11A, 0.37 g of C26A, 0.36 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.47 g of 1-[3-methyl-2-(1-naphthalen-2-ylethylideneaminooxymethyl)phenyl]-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 36).

(111) ##STR00154##

(112) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.84-7.75 (5H, m), 7.47-7.21 (5H, m), 5.31 (2H, s), 3.59 (3H, s), 2.56 (3H, s), 2.21 (3H, s).

Production Example 37

(113) A mixture of 0.56 g of C11A, 0.36 g of C22A, 0.36 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.42 g of 1-{3-methyl-2-[1-(3-nitrophenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 37).

(114) ##STR00155##

(115) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.40 (1H, s), 8.18-8.15 (1H, m), 7.93-7.90 (1H, m), 7.50 (1H, t, J=7.9 Hz), 7.38 (2H, d, J=5.1 Hz), 7.23 (1H, t, J=4.5 Hz), 5.29 (2H, s), 3.69 (3H, s), 2.56 (3H, s), 2.15 (3H, s).

Production Example 38

(116) A mixture of 0.56 g of C11A, 0.33 g of C23A, 0.36 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.51 g of 1-{3-methyl-2-[1-(3,5-dimethylphenyl)ethylideneaminooxymethyl]phen yl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 38).

(117) ##STR00156##

(118) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.37-7.36 (2H, m), 7.25-7.19 (3H, m), 6.97 (1H, bs), 5.24 (2H, s), 3.63 (3H, s), 2.54 (3H, s), 2.32 (6H, s), 2.08 (3H, s).

Production Example 39

(119) A mixture of 0.56 g of C11A, 0.41 g of C31A, 0.36 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.54 g of 1-{3-methyl-2-[1-(3,5-dichlorophenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 39).

(120) ##STR00157##

(121) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.46-7.23 (6H, m), 5.26 (2H, s), 3.68 (3H, s), 2.54 (3H, s), 2.06 (3H, s).

Production Example 40

(122) A mixture of 0.56 g of C11A, 0.37 g of C33A, 0.36 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.43 g of 1-{3-methyl-2-[1-(3,5-ditrifluoromethylphenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 40).

(123) ##STR00158##

(124) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.02 (2H, bs), 7.83 (1H, bs), 7.40-7.39 (2H, m), 7.23 (1H, t, J=4.8 Hz), 5.29 (2H, s), 3.68 (3H, s), 2.54 (3H, s), 2.16 (3H, s).

Production Example 41

(125) A mixture of 0.45 g of C8A, 0.25 g of C28A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.25 g of 1-{3-methoxy-2-[1-(3-chlorophenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 41).

(126) ##STR00159##

(127) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.56 (1H, m), 7.45-7.40 (2H, m), 7.30-7.23 (2H, m), 7.07 (1H, d, J=8.5 Hz), 7.01 (1H, d, J=8.0 Hz), 5.40 (2H, s), 3.92 (3H, s), 3.58 (3H, s), 2.03 (3H, s).

Production Example 42

(128) A mixture of 0.45 g of C8A, 0.33 g of C34A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.35 g of 1-{3-methoxy-2-[1-(3-trifluoromethoxyphenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 42).

(129) ##STR00160##

(130) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.48-7.41 (3H, m), 7.34 (1H, t, J=7.9 Hz), 7.19-7.16 (1H, m), 7.07 (1H, dd, J=8.2, 0.8 Hz), 7.01 (1H, dd, J=8.2, 0.8 Hz), 5.40 (2H, s), 3.92 (3H, s), 3.57 (3H, s), 2.05 (3H, s).

Production Example 43

(131) A mixture of 0.45 g of C8A, 0.38 g of C57A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.30 g of 1-(3-methoxy-2-{1-[3-(1,1,2,2-tetrafluoroethoxyl)phenyl]ethylideneaminooxymethyl}phenyl)-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 43).

(132) ##STR00161##

(133) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.47-7.41 (3H, m), 7.34 (1H, t, J=8.0 Hz), 7.19-7.17 (1H, m), 7.07 (1H, dd, J=8.5, 0.7 Hz), 7.01 (1H, dd, J=8.0, 1.0 Hz), 5.93 (1H, tt, J=53.0, 2.9 Hz), 5.40 (2H, s), 3.92 (3H, s), 3.57 (3H, s), 2.05 (3H, s).

Production Example 44

(134) A mixture of 0.45 g of C8A, 0.25 g of C21A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.32 g of 1-{3-methoxy-2-[1-(3-methoxyphenyl)ethylideneaminooxymethyl]phenyl }-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 44).

(135) ##STR00162##

(136) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.43 (1H, t, J=8.2 Hz), 7.23 (1H, d, J=8.2 Hz), 7.13-7.11 (2H, m), 7.07 (1H, d, J=8.5 Hz), 7.00 (1H, d, J=8.0 Hz), 6.89-6.86 (1H, m), 5.39 (2H, s), 3.92 (3H, s), 3.82 (3H, s), 3.55 (3H, s), 2.04 (3H, s).

Production Example 45

(137) A mixture of 0.45 g of C8A, 0.27 g of C22A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.38 g of 1-{3-methoxy-2-[1-(3-nitrophenyl)ethyl ideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 45).

(138) ##STR00163##

(139) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.39 (1H, t, J=2.1 Hz), 8.16 (1H, dq, J=8.2, 1.1 Hz), 7.89 (1H, dq, J=7.8, 0.89 Hz), 7.49 (1H, t, J=8.1 Hz), 7.45 (1H, t, J=8.1 Hz), 7.09 (1H, d, J=8.5 Hz), 7.01 (1H, d, J=8.0 Hz), 5.41 (2H, s), 3.94 (3H, s), 3.63 (3H, s), 2.10 (3H, s).

Production Example 46

(140) A mixture of 0.45 g of C8A, 0.26 g of C30A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.25 g of 1-{3-methoxy-2-[1-(indan-5-yl)ethylideneaminooxymethyl]phenyl}-4-m ethyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 46).

(141) ##STR00164##

(142) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.43-7.40 (2H, m), 7.32-7.30 (1H, m), 7.17 (1H, d, J=7.7 Hz), 7.03 (2H, dd, J=19.3, 8.2 Hz), 5.39 (2H, s), 3.90 (3H, s), 3.54 (3H, s), 2.89 (4H, m), 2.07-2.03 (2H, m), 2.04 (3H, s).

Production Example 47

(143) A mixture of 0.45 g of C8A, 0.28 g of C26A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.38 g of 1-{3-methoxy-2-[l-(naphthalen-2-yl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 47).

(144) ##STR00165##

(145) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.93 (1H, s), 7.85-7.76 (4H, m), 7.48-7.42 (3H, m), 7.08 (1H, d, J=8.5 Hz), 7.02 (1H, d, J=8.1 Hz), 5.46 (2H, s), 3.93 (3H, s), 3.51 (3H, s), 2.17 (3H, s).

Production Example 48

(146) A mixture of 0.45 g of C8A, 0.24 g of C23A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.27 g of 1-{3-methoxy-2-[1-(3,5-dimethylphenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 48).

(147) ##STR00166##

(148) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.42 (1H, t, J=8.2 Hz), 7.17 (2H, s), 7.06 (1H, d, J=8.5 Hz), 7.01 (1H, d, J=8.0 Hz), 6.96 (1H, s), 5.39 (2H, s), 3.91 (3H, s), 3.54 (3H, s), 2.31 (6H, s), 2.03 (3H, s).

Production Example 49

(149) A mixture of 0.45 g of C8A, 0.30 g of C31A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.48 g of 1-{3-methoxy-2-[1-(3,5-dichlorophenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 49).

(150) ##STR00167##

(151) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.46-7.42 (3H, m), 7.30 (1H, t, J=1.8 Hz), 7.04 (2H, dd, J=27.2, 8.1 Hz), 5.39 (2H, s), 3.93 (3H, s), 3.63 (3H, s), 2.01 (3H, s).

Production Example 50

(152) A mixture of 0.42 g of C11A, 0.28 g of C38A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1-methyl-4-{3-methyl-2-[1-(3-trifluoromethylphenyl)methylideneaminooxymethyl]phenyl}-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 50).

(153) ##STR00168##

(154) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.98 (1H, s), 7.79 (1H, s), 7.66 (1H, d, J=7.8 Hz), 7.58 (1H, d, J=7.6 Hz), 7.45 (1H, t, J=7.8 Hz), 7.41-7.37 (2H, m), 7.25-7.23 (1H, m), 5.24 (2H, s), 3.69 (3H, s), 2.54 (3H, s).

Production Example 51

(155) A mixture of 0.42 g of C11A, 0.33 g of C39A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1-methyl-4-{3-methyl-2-[1-(3-trifluoromethylphenyl)propylideneaminooxymethyl]phenyl}-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 51).

(156) ##STR00169##

(157) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.84 (1H, s), 7.74 (1H, d, J=7.8 Hz), 7.58 (1H, d, J=7.8 Hz), 7.46 (1H, t, J=7.8 Hz), 7.40-7.36 (2H, m), 7.25-7.22 (1H, m), 5.25 (2H, s), 3.66 (3H, s), 2.65 (2H, q, J=7.6 Hz), 2.55 (3H, s), 1.04 (3H, t, J=7.6 Hz).

Production Example 52

(158) A mixture of 0.42 g of C11A, 0.37 g of C64A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.34 g of 1-{3-methyl-2-[2,2-dimethyl-1-(3-trifluoromethylphenyl)pyrrolideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 52).

(159) ##STR00170##

(160) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.54 (1H, d, J=7.3 Hz), 7.43 (1H, t, J=7.8 Hz), 7.32-7.29 (2H, m), 7.16 (1H, d, J=7.3 Hz), 7.11 (1H, s), 7.07 (1H, d, J=7.6 Hz), 5.00 (2H, s), 3.64 (3H, s), 2.27 (3H, s), 1.03 (9H, s).

Production Example 53

(161) A mixture of 0.46 g of C17A, 0.25 g of C28A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.42 g of 1-{3-cyclopropyl-2-[1-(3-chlorophenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 53).

(162) ##STR00171##

(163) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.58 (1H, t, J=1.6 Hz), 7.44 (1H, dt, J=7.3, 1.6 Hz), 7.39 (1H, t, J=7.9 Hz), 7.31-7.20 (4H, m), 5.49 (2H, s), 3.64 (3H, s), 2.30-2.19 (1H, m), 2.08 (3H, s), 1.06-1.04 (2H, m), 0.79-0.77 (2H, m).

Production Example 54

(164) A mixture of 0.46 g of C17A, 0.33 g of C34A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.55 g of 1-{3-cyclopropyl-2-[1-(3-trifluoromethoxyphenyl)ethylideneaminooxy methyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 54).

(165) ##STR00172##

(166) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.45-7.39 (4H, m), 7.25-7.19 (3H, m), 5.50 (2H, s), 3.64 (3H, s), 2.27-2.20 (1H, m), 2.09 (3H, s), 1.08-1.03 (2H, m), 0.80-0.76 (2H, m).

Production Example 55

(167) A mixture of 0.46 g of C17A, 0.50 g of C57A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.16 g of 1-(3-cyclopropyl-2-{1-[3-(1,1,2,2-tetrafluoroethoxyl)phenyl]ethylideneaminooxymethyl}phenyl)-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 55).

(168) ##STR00173##

(169) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.48-7.45 (2H, m), 7.41-7.33 (2H, m), 7.23-7.19 (3H, m), 5.93 (1H, tt, J=53.2, 2.9 Hz), 5.50 (2H, s), 3.63 (3H, s), 2.28-2.20 (1H, m), 2.09 (3H, s), 1.07-1.02 (2H, m), 0.79-0.76 (2H, m).

Production Example 56

(170) A mixture of 0.46 g of C17A, 0.33 g of C21A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.31 g of 1-{3-cyclopropyl-2-[1-(3-methoxyphenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 56).

(171) ##STR00174##

(172) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.38 (1H, t, J=7.9 Hz), 7.25-7.22 (3H, m), 7.16-7.12 (2H, m), 6.88 (1H, dq, J=8.2, 1.9 Hz), 5.48 (2H, s), 3.83 (3H, s), 3.62 (3H, s), 2.31-2.19 (1H, m), 2.09 (3H, s), 1.05-1.03 (2H, m), 0.78-0.77 (2H, m).

Production Example 57

(173) A mixture of 0.46 g of C17A, 0.27 g of C22A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.36 g of 1-{3-cyclopropyl-2-[1-(3-nitrophenyl)ethylideneaminooxymethyl]phen yl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 57).

(174) ##STR00175##

(175) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.42 (1H, t, J=1.8 Hz), 8.18 (1H, dq, J=8.2, 1.2 Hz), 7.92 (1H, dq, J=7.8, 0.9 Hz), 7.51 (1H, t, J=8.2 Hz), 7.40 (1H, t, J=7.8 Hz), 7.25-7.22 (2H, m), 5.51 (2H, s), 3.68 (3H, s), 2.28-2.20 (1H, m), 2.15 (3H, s), 1.08-1.06 (2H, m), 0.81-0.77 (2H, m).

Production Example 58

(176) A mixture of 0.46 g of C17A, 0.26 g of C30A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.36 g of 1-{3-cyclopropyl-2-[1-(indan-5-yl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 58).

(177) ##STR00176##

(178) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.45 (1H, s), 7.37 (1H, t, J=7.9 Hz), 7.33 (1H, dd, J=7.9, 1.6 Hz), 7.23-7.17 (3H, m), 5.47 (2H, s), 3.61 (3H, s), 2.89 (4H, m), 2.27-2.20 (1H, m), 2.09 (3H, s), 2.06-2.03 (2H, m), 1.06-1.01 (2H, m), 0.79-0.75 (2H, m).

Production Example 59

(179) A mixture of 0.46 g of C17A, 0.28 g of C26A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.47 g of 1-{3-cyclopropyl-2-[1-(naphthalen-2-yl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 59).

(180) ##STR00177##

(181) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.94 (1H, s), 7.84-7.76 (4H, m), 7.48-7.44 (2H, m), 7.37 (1H, t, J=7.9 Hz), 7.22 (2H, d, J=8.0 Hz), 5.55 (2H, s), 3.57 (3H, s), 2.29-2.24 (1H, m), 2.21 (3H, s), 1.07-1.02 (2H, m), 0.80-0.76 (2H, m).

Production Example 60

(182) A mixture of 0.46 g of C17A, 0.24 g of C23A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.42 g of 1-{3-cyclopropyl-2-[1-(3,5-dimethylphenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 60).

(183) ##STR00178##

(184) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.37 (1H, t, J=7.9 Hz), 7.25-7.19 (4H, m), 6.97 (1H, s), 5.47 (2H, s), 3.61 (3H, s), 2.31 (6H, s), 2.29-2.20 (1H, m), 2.08 (3H, s), 1.06-1.01 (2H, m), 0.79-0.75 (2H, m).

Production Example 61

(185) A mixture of 0.46 g of C17A, 0.30 g of C31A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.46 g of 1-{3-cyclopropyl-2-[1-(3,5-dichlorophenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 61).

(186) ##STR00179##

(187) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.46 (2H, d, J=1.7 Hz), 7.40 (1H, t, J=7.9 Hz), 7.32 (1H, t, J=1.9 Hz), 7.23 (2H, t, J=8.0 Hz), 5.49 (2H, s), 3.67 (3H, s), 2.26-2.17 (1H, m), 2.06 (3H, s), 1.08-1.04 (2H, m), 0.80-0.76 (2H, m).

Production Example 62

(188) A mixture of 0.31 g of C17A, 0.20 g of C36A, 0.18 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.42 g of 1-{3-cyclopropyl-2-[1-(4-trifluoromethylphenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 62).

(189) ##STR00180##

(190) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.69 (2H, d, J=8.2 Hz), 7.59 (2H, d, J=8.2 Hz), 7.40 (1H, t, J=7.9 Hz), 7.25-7.21 (2H, m), 5.51 (2H, s), 3.63 (3H, s), 2.28-2.18 (1H, m), 2.12 (3H, s), 1.08-1.03 (2H, m), 0.80-0.76 (2H, m).

Production Example 63

(191) A mixture of 0.42 g of C11A, 0.39 g of C74A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.10 g of 1-methyl-4-{3-methyl-2-[2,2,2-trifluoro-1-(3-trifluoromethylphenyl)ethylideneaminooxymethyl]phenyl}-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 63).

(192) ##STR00181##

(193) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.70-7.67 (1H, m), 7.62 (1H, s), 7.54 (2H, d, J=5.1 Hz), 7.43-7.36 (2H, m), 7.29-7.23 (1H, m), 5.32 (2H, s), 3.65 (3H, s), 2.44 (3H, s).

Production Example 64

(194) A mixture of 0.60 g of C9A, 1.00 g of C42A, 0.56 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1.26 g of 1-{3-trifluoromethyl-2-[1-(3-trifluoromethylphenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 64).

(195) ##STR00182##

(196) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.89 (1H, dd, J=6.5, 2.7 Hz), 7.79 (1H, s), 7.72 (1H, d, J=8.0 Hz), 7.65-7.58 (3H, m), 7.45 (1H, t, J=7.7 Hz), 5.52 (2H, s), 3.58 (3H, s), 2.06 (3H, s).

Production Example 65

(197) A mixture of 0.50 g of C11A, 0.35 g of C19A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.46 g of 1-{3-methyl-2-[1-(3-bromo-4-fluorophenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 65).

(198) ##STR00183##

(199) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.79 (1H, dd, J=6.6, 2.30 Hz), 7.49 (1H, dq, J=8.7, 2.3 Hz), 7.39-7.39 (1H, m), 7.38 (1H, s), 7.25-7.20 (1H, m), 7.08 (1H, t, J=8.5 Hz), 5.24 (2H, s), 3.67 (3H, s), 2.54 (3H, s), 2.07 (3H, s).

Production Example 66

(200) A mixture of 0.50 g of C11A, 0.31 g of C43A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.50 g of 1-{3-methyl-2-[1-(3,4dichlorophenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 66).

(201) ##STR00184##

(202) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.67 (1H, dd, J=1.5, 0.7 Hz), 7.41-7.36 (4H, m), 7.24-7.20 (1H, m), 5.25 (2H, s), 3.66 (3H, s), 2.54 (3H, s), 2.06 (3H, s).

Production Example 67

(203) A mixture of 0.50 g of C11A, 0.26 g of C44A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.38 g of 1-{3-methyl-2-[1-(3,4-difluorophenyl)ethylideneaminooxymethyl]phen yl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 67).

(204) ##STR00185##

(205) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.47-7.37 (3H, m), 7.30-7.27 (1H, m), 7.25-7.20 (1H, m), 7.15-7.08 (1H, m), 5.24 (2H, s), 3.67 (3H, s), 2.55 (3H, s), 2.07 (3H, s).

Production Example 68

(206) A mixture of 0.47 g of C13A, 0.30 g of C42A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.38 g of 1-{3-ethoxy-2-[1-(3-trifluoromethylphenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 68).

(207) ##STR00186##

(208) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.84 (1H, s), 7.72 (1H, d, J=7.8 Hz), 7.56 (1H, d, J=7.8 Hz), 7.46-7.38 (2H, m), 7.05 (1H, d, J=8.2 Hz), 6.99 (1H, d, J=8.0 Hz), 5.43 (2H, s), 4.13 (2H, q, J=7.0 Hz), 3.57 (3H, s), 2.07 (3H, s), 1.46 (3H, t, J=7.0 Hz).

Production Example 69

(209) A mixture of 0.42 g of C11A, 0.28 g of C45A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.39 g of 1-{3-methyl-2-[1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 69).

(210) ##STR00187##

(211) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.36 (2H, d, J=4.8 Hz), 7.28 (2H, d, J=7.1 Hz), 7.21 (1H, t, J=4.6 Hz), 7.02 (1H, d, J=8.5 Hz), 5.23 (2H, s), 3.64 (3H, s), 2.80-2.71 (4H, m), 2.54 (3H, s), 2.07 (3H, s), 1.81-1.75 (4H, m).

Production Example 70

(212) A mixture of 0.42 g of C11A, 0.53 g of C59A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography and further subjected to gel permeation chromatography to obtain 0.40 g of 1-{2-[cyclopropyl(3-trifluoromethylphenyl)methylideneaminooxymethyl]-3-methylphenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 70).

(213) ##STR00188##

(214) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.66 (0.8H, s), 7.59-7.56 (2.0H, m), 7.51-7.40 (1.4H, m), 7.39-7.30 (2.0H, m), 7.23 (0.8H, t, J=4.6 Hz), 5.24 (1.6H, s), 5.05 (0.4H, s), 3.62 (0.6H, s), 3.61 (2.4H, s), 2.55 (2.4H, s), 2.37 (0.6H, s), 2.04-1.97 (0.8H, m), 1.61-1.54 (0.2H, m), 0.90-0.85 (1.6H, m), 0.78-0.72 (0.8H, m), 0.54-0.50 (1.6H, m).

Production Example 71

(215) A mixture of 0.42 g of C11A, 0.23 g of C46A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.36 g of 1-{3-methyl-2-[1-(3-methylphenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 71).

(216) ##STR00189##

(217) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.41 (1H, s), 7.37-7.34 (3H, m), 7.25-7.20 (2H, m), 7.14 (1H, d, J=7.6 Hz), 5.25 (2H, s), 3.62 (3H, s), 2.55 (3H, s), 2.36 (3H, s), 2.09 (3H, s).

Production Example 72

(218) A mixture of 0.42 g of C11A, 0.35 g of C67A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.40 g of 1-{3-methyl-2-[1-(3-hexyloxyphenyl) ethyl ideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 72).

(219) ##STR00190##

(220) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.36 (2H, d, J=5.3 Hz), 7.25-7.20 (2H, m), 7.14-7.10 (2H, m), 6.88-6.85 (1H, m), 5.25 (2H, s), 3.97 (2H, t, J=6.5 Hz), 3.63 (3H, s), 2.54 (3H, s), 2.09 (3H, s), 1.81-1.74 (2H, m), 1.50-1.43 (2H, m), 1.37-1.32 (4H, m), 0.93-0.89 (3H, m).

Production Example 73

(221) A mixture of 0.42 g of C11A, 0.35 g of C60A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography and further subjected to gel permeation chromatography to obtain 0.46 g of 1-methyl-4-{3-methyl-2-[2-methyl-1-(3-trifluoromethylphenyl)propylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 73).

(222) ##STR00191##

(223) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.61-7.53 (2.1H, m), 7.47-7.41 (1.1H, m), 7.39-7.29 (2.5H, m), 7.26-7.22 (0.8H, m), 7.18 (0.5H, dd, J=7.2, 1.7 Hz), 5.20 (1.0H, s), 5.06 (1.0H, s), 3.62 (1.5H, s), 3.62 (1.5H, s), 3.37 (0.5H, sep, J=7.1 Hz), 3.37 (0.5H, sep, J=6.9 Hz), 2.54 (1.5H, s), 2.35 (1.5H, s), 1.10 (3.0H, d, J=7.1 Hz), 1.00 (3.0H, d, J=6.9 Hz).

Production Example 74

(224) A mixture of 0.42 g of C11A, 0.29 g of C65A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.46 g of N-(3-{1-[2-methyl-6-(4-methyl-5-oxo-4,5-dihydrotetrazol-1-yl)benzyloxyamino]ethyl}phenyl)acetamide (hereinafter referred to as the present compound 74).

(225) ##STR00192##

(226) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.07 (1H, bs), 7.97 (1H, d, J=8.0 Hz), 7.49 (1H, s), 7.41-7.36 (2H, m), 7.28-7.24 (2H, m), 7.15 (1H, d, J=8.0 Hz), 5.25 (2H, s), 3.67 (3H, s), 2.55 (3H, s), 2.20 (3H, s), 2.09 (3H, s).

Production Example 75

(227) A mixture of 0.42 g of C11A, 0.35 g of C66A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.31 g of N-methyl-N-(3-{1-[2-methyl-6-(4-methyl-5-oxo-4,5-dihydrotetrazol-1-yl)benzyloxyimino]ethyl}phenyl)acetamide (hereinafter referred to as the present compound 75).

(228) ##STR00193##

(229) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.52-7.36 (5H, m), 7.22 (1H, t, J=4.7 Hz), 7.15 (1H, d, J=7.8 Hz), 5.25 (2H, s), 3.68 (3H, s), 3.27 (3H, s), 2.56 (3H, s), 2.11 (3H, s), 1.87 (3H, s).

Production Example 76

(230) A mixture of 0.28 g of C11A, 0.18 g of C68A, 0.18 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.09 g of 1-{3-methyl-2-[1-(3-isopropoxyphenyl)ethylideneiminooxymethyl]phen yl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 76).

(231) ##STR00194##

(232) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.37 (2H, d, J=4.8 Hz), 7.24-7.20 (2H, m), 7.12-7.10 (2H, m), 6.87-6.84 (1H, m), 5.25 (2H, s), 4.58 (1H, sep, J=6.1 Hz), 3.64 (3H, s), 2.55 (3H, s), 2.08 (3H, s), 1.33 (6H, d, J=6.2 Hz).

Production Example 77

(233) A mixture of 0.28 g of C11A, 0.22 g of C70A, 0.18 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.23 g of 1-{3-methyl-2-[1-(3-trifluoromethylphenyl)butylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 77).

(234) ##STR00195##

(235) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.83 (1H, s), 7.73 (1H, d, J=7.8 Hz), 7.58 (1H, d, J=8.0 Hz), 7.46 (1H, t, J=7.9 Hz), 7.38 (2H, m), 7.23 (1H, t, J=4.7 Hz), 5.25 (2H, s), 3.67 (3H, s), 2.64-2.60 (2H, m), 2.56 (3H, s), 1.51-1.38 (2H, m), 0.89 (3H, t, J=7.4 Hz).

Production Example 78

(236) A mixture of 0.28 g of C11A, 0.26 g of C50A, 0.18 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.16 g of 1-{3-methyl-2-[1-(3-iodophenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 78).

(237) ##STR00196##

(238) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.93 (1H, t, J=1.6 Hz), 7.66 (1H, dq, J=7.8, 0.92 Hz), 7.52 (1H, dq, J=7.9, 0.92 Hz), 7.39-7.38 (2H, m), 7.23 (1H, t, J=4.6 Hz), 7.07 (1H, t, J=7.7 Hz), 5.26 (2H, s), 3.66 (3H, s), 2.55 (3H, s), 2.07 (3H, s).

Production Example 79

(239) A mixture of 0.28 g of C11A, 0.20 g of C51A, 0.18 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.29 g of 1-{3-methyl-2-[1-(3-bromophenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 79).

(240) ##STR00197##

(241) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.74 (1H, t, J=1.8 Hz), 7.50-7.44 (2H, m), 7.38-7.37 (2H, m), 7.25-7.18 (2H, m), 5.26 (2H, s), 3.66 (3H, s), 2.55 (3H, s), 2.08 (3H, s).

Production Example 80

(242) A mixture of 0.42 g of C11A, 0.38 g of 1-(3-trifluoromethylphenyl)pentan-1-one oxime mentioned in Reference Production Example 61, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.50 g of 1-{3-methyl-2-[1-(3-trifluoromethylphenyl)pentylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 80).

(243) ##STR00198##

(244) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.83 (1H, s), 7.72 (1H, d, J=7.8 Hz), 7.58 (1H, d, J=7.8 Hz), 7.46 (1H, t, J=7.9 Hz), 7.38 (2H, d, J=5.3 Hz), 7.22 (1H, t, J=4.6 Hz), 5.24 (2H, s), 3.67 (3H, s), 2.63 (2H, t, J=7.7 Hz), 2.56 (3H, s), 1.43-1.25 (4H, m), 0.86 (3H, t, J=7.2 Hz).

Production Example 81

(245) A mixture of 0.28 g of C11A, 0.27 g of C62A, 0.18 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.36 g of 1-{3-methyl-2-[1-(3-trifluoromethylphenyl)heptylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 81).

(246) ##STR00199##

(247) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.82 (1H, s), 7.71 (1H, d, J=7.8 Hz), 7.57 (1H, d, J=7.8 Hz), 7.45 (1H, t, J=7.9 Hz), 7.38 (2H, d, J=4.1 Hz), 7.22 (1H, t, J=4.6 Hz), 5.23 (2H, s), 3.66 (3H, s), 2.62 (2H, t, J=7.9 Hz), 2.55 (3H, s), 1.43-1.36 (2H, m), 1.31-1.20 (6H, m), 0.83 (3H, t, J=6.1 Hz).

Production Example 82

(248) A mixture of 0.28 g of C11A, 0.25 g of C63A, 0.18 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.31 g of 1-methyl-4-{3-methyl-2-[3-methyl-1-(3-trifluoromethylphenyl)butylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 82).

(249) ##STR00200##

(250) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.82 (1H, s), 7.72 (1H, d, J=7.8 Hz), 7.57 (1H, d, J=7.8 Hz), 7.45 (1H, t, J=7.8 Hz), 7.38-7.37 (2H, m), 7.22 (1H, t, J=4.7 Hz), 5.23 (2H, s), 3.65 (3H, s), 2.56 (5H, m), 1.80 (1H, sep, J=6.8 Hz), 0.82 (6H, d, J=6.7 Hz).

Production Example 83

(251) A mixture of 0.28 g of C11A, 0.22 g of C47A, 0.18 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.19 g of 1-{3-methyl-2-[1-(2-trifluoromethylphenyl) propylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 83).

(252) ##STR00201##

(253) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.68 (1H, d, J=8.0 Hz), 7.54 (1H, t, J=6.6 Hz), 7.46 (1H, t, J=8.0 Hz), 7.39-7.38 (2H, m), 7.29-7.28 (1H, m), 7.24-7.22 (1H, m), 5.17 (2H, s), 3.65 (3H, s), 2.58 (2H, q, J=7.7 Hz), 2.52 (3H, s), 0.88 (3H, t, J=7.7 Hz).

Production Example 84

(254) A mixture of 0.28 g of C11A, 0.22 g of C48A, 0.18 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.32 g of 1-{3-methyl-2-[1-(4-trifluoromethylphenyl)propylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 84).

(255) ##STR00202##

(256) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.68 (2H, d, J=8.5 Hz), 7.59 (2H, d, J=8.5 Hz), 7.39-7.37 (2H, m), 7.25-7.21 (1H, m), 5.25 (2H, s), 3.66 (3H, s), 2.65 (2H, q, J=7.7 Hz), 2.55 (3H, s), 1.03 (3H, t, J=7.6 Hz).

Production Example 85

(257) A mixture of 0.28 g of C11A, 0.22 g of C69A, 0.18 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.25 g of 1-{3-methyl-2-[1-(3-pentyloxyphenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 85).

(258) ##STR00203##

(259) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.37 (2H, d, J=4.4 Hz), 7.25-7.21 (2H, m), 7.13-7.11 (2H, m), 6.88-6.86 (1H, m), 5.25 (2H, s), 3.97 (2H, t, J=6.5 Hz), 3.64 (3H, s), 2.55 (3H, s), 2.09 (3H, s), 1.82-1.75 (2H, m), 1.49-1.34 (4H, m), 0.94 (3H, t, J=7.1 Hz).

Production Example 86

(260) A mixture of 0.31 g of C17A, 0.20 g of C58A, 0.18 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.40 g of 1-{3-cyclopropy-2-[1-(3-difluoromethoxyphenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 86).

(261) ##STR00204##

(262) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.41-7.36 (3H, m), 7.32 (1H, t, J=7.9 Hz), 7.22 (2H, t, J=8.7 Hz), 7.09 (1H, dd, J=7.8, 1.6 Hz), 6.58 (1H, t, J=74.0 Hz), 5.48 (2H, s), 3.65 (3H, s), 2.30-2.20 (1H, m), 2.09 (3H, s), 1.08-1.03 (2H, m), 0.80-0.76 (2H, m).

Production Example 87

(263) A mixture of 0.28 g of C11A, 0.20 g of C71A, 0.18 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.27 g of 1-(3-methyl-2-{1-[3-(butyn-2-yloxy)phenyl]ethylideneaminooxymethyl)phenyl-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 87).

(264) ##STR00205##

(265) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.36 (2H, d, J=4.4 Hz), 7.27-7.16 (4H, m), 6.95-6.93 (1H, m), 5.25 (2H, s), 4.68-4.65 (2H, m), 3.64 (3H, s), 2.55 (3H, s), 2.09 (3H, s), 1.87-1.85 (3H, m).

Production Example 88

(266) A mixture of 0.28 g of C11A, 0.22 g of C72A, 0.18 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.16 g of 1-(3-methyl-2-{1-[3-(pentyn-2-yloxy)phenyl]ethylideneaminooxymethyl}phenyl)-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 88).

(267) ##STR00206##

(268) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.36 (2H, d, J=4.6 Hz), 7.26-7.16 (4H, m), 6.94 (1H, dd, J=7.9, 2.4 Hz), 5.25 (2H, s), 4.68 (2H, t, J=2.3 Hz), 3.63 (3H, s), 2.54 (3H, s), 2.23 (2H, tq, J=7.6, 2.3 Hz), 2.09 (3H, s), 1.13 (3H, t, J=7.6 Hz).

Production Example 89

(269) A mixture of 0.31 g of C17A, 0.19 g of C55A, 0.18 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1-{3-cyclopropyl-2-[1-(3-difluoromethylphenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 89).

(270) ##STR00207##

(271) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.75 (1H, s), 7.67 (1H, d, J=7.6 Hz), 7.49 (1H, d, J=7.6 Hz), 7.4 (1H, d, J=7.8 Hz), 7.39 (1H, t, J=7.7 Hz), 7.23 (2H, t, J=7.7 Hz), 6.67 (1H, t, J=56.3 Hz), 5.49 (2H, s), 3.63 (3H, s), 2.30-2.18 (1H, m), 2.12 (3H, s), 1.08-1.03 (2H, m), 0.80-0.76 (2H, m).

Production Example 90

(272) A mixture of 0.31 g of C17A, 0.18 g of C40A, 0.18 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1-[2-(1-benzo[1,3]dioxan-5-yl-ethylideneaminooxymethyl)-3-cyclopropylphenyl]-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 90).

(273) ##STR00208##

(274) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.38 (1H, t, J=7.8 Hz), 7.22 (2H, t, J=7.6 Hz), 7.14 (1H, s), 7.02 (1H, dd, J=8.1, 1.7 Hz), 6.76 (1H, d, J=8.2 Hz), 5.96 (2H, s), 5.45 (2H, s), 3.65 (3H, s), 2.27-2.20 (1H, m), 2.05 (3H, s), 1.07-1.02 (2H, m), 0.79-0.75 (2H, m).

Production Example 91

(275) A mixture of 0.31 g of C17A, 0.22 g of C56A, 0.18 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1-{3-cyclopropyl-2-[1-(2,2-difluorobenzo[1,3]dioxol-5-yl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 91).

(276) ##STR00209##

(277) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.41-7.37 (2H, m), 7.27-7.21 (3H, m), 7.00 (1H, d, J=8.5 Hz), 5.47 (2H, s), 3.66 (3H, s), 2.26-2.19 (1H, m), 2.08 (3H, s), 1.08-1.02 (2H, m), 0.80-0.76 (2H, m).

Production Example 92

(278) A mixture of 0.31 g of C18A, 0.20 g of C42A, 0.18 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography and further subjected to gel permeation chromatography to obtain 0.26 g of 1-{3-methylthio-2-[1-(3-trifluoromethylphenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 92).

(279) ##STR00210##

(280) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.85 (1H, s), 7.75 (1H, d, J=8.0 Hz), 7.58 (1H, d, J=7.8 Hz), 7.50-7.43 (3H, m), 7.20 (1H, dd, J=7.3, 1.8 Hz), 5.42 (2H, s), 3.64 (3H, s), 2.55 (3H, s), 2.13 (3H, s).

Production Example 93

(281) A mixture of 0.35 g of C5A, 0.20 g of C42A, 0.18 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.30 g of 1-{3-bromo-2-[1-(3-trifluoromethylphenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 93).

(282) ##STR00211##

(283) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.82 (1H, s), 7.78 (1H, dd, J=6.8, 2.6 Hz), 7.74 (1H, d, J=8.0 Hz), 7.58 (1H, d, J=7.8 Hz), 7.45 (1H, t, J=7.9 Hz), 7.38-7.32 (2H, m), 5.47 (2H, s), 3.62 (3H, s), 2.11 (3H, s).

Production Example 94

(284) A mixture of 0.16 g of C7A, 0.20 g of C42A, 0.18 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.11 g of 1-{3-iodo-2-[1-(3-trifluoromethylphenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 94).

(285) ##STR00212##

(286) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.06 (1H, d, J=8.0 Hz), 7.85 (1H, s), 7.75 (1H, d, J=8.0 Hz), 7.59 (1H, d, J=8.0 Hz), 7.45 (1H, t, J=7.8 Hz), 7.38 (1H, dd, J=7.9, 1.0 Hz), 7.17 (1H, t, J=7.9 Hz), 5.43 (2H, s), 3.63 (3H, s), 2.14 (3H, s).

Production Example 95

(287) A mixture of 0.28 g of C11A, 0.19 g of C27A, 0.18 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.29 g of 1-{3-methyl-2-[1-(naphthalen-1-yl)ethylideneaminooxymethyl]-phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 95).

(288) ##STR00213##

(289) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.92-7.89 (1H, m), 7.85-7.81 (2H, m), 7.48-7.37 (6H, m), 7.29-7.27 (1H, m), 5.32 (2H, s), 3.57 (3H, s), 2.56 (3H, s), 2.22 (3H, s).

Production Example 96

(290) A mixture of 0.28 g of C11A, 0.15 g of C52A, 0.18 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.15 g of 1-{3-methyl-2-[1-(2-methylphenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 96).

(291) ##STR00214##

(292) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.38-7.37 (2H, m), 7.25-7.19 (2H, m), 7.17-7.15 (3H, m), 5.24 (2H, s), 3.62 (3H, s), 2.53 (3H, s), 2.22 (3H, s), 2.04 (3H, s).

Production Example 97

(293) A mixture of 0.42 g of C11A, 0.25 g of C54A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1-{3-methyl-2-[1-(2-methoxyphenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 97).

(294) ##STR00215##

(295) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.38-7.37 (2H, m), 7.31 (1H, td, J=7.8, 1.7 Hz), 7.25-7.21 (2H, m), 6.94-6.86 (2H, m), 5.23 (2H, s), 3.80 (3H, s), 3.65 (3H, s), 2.54 (3H, s), 2.06 (3H, s).

Production Example 98

(296) A mixture of 0.42 g of C11A, 0.25 g of C53A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1-{3-methyl-2-[1-(2-chlorophenyl)ethylideneaminooxymethyl]-phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 98).

(297) ##STR00216##

(298) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.39-7.23 (7H, m), 5.25 (2H, s), 3.65 (3H, s), 2.54 (3H, s), 2.09 (3H, s).

Production Example 99

(299) A mixture of 0.28 g of C11A, 0.24 g of C49A, 0.18 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.26 g of 1-{3-methyl-2-[1-(3-fluoro-5-trifluoromethylphenyl)propylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 99).

(300) ##STR00217##

(301) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.62 (1H, s), 7.47 (1H, dt, J=9.8, 1.8 Hz), 7.40-7.38 (2H, m), 7.29 (1H, d, J=8.2 Hz), 7.23 (1H, t, J=4.7 Hz), 5.25 (2H, s), 3.69 (3H, s), 2.62 (2H, q, J=7.6 Hz), 2.55 (3H, s), 1.04 (3H, t, J=7.6 Hz).

Production Example 100

(302) A mixture of 0.46 g of C17A, 0.33 g of C39A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.45 g of 1-{3-cyclopropyl-2-[1-(3-trifluoromethylphenyl)propylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 100).

(303) ##STR00218##

(304) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.84 (1H, s), 7.74 (1H, d, J=7.8 Hz), 7.59 (1H, d, J=7.8 Hz), 7.46 (1H, t, J=7.8 Hz), 7.40 (1H, t, J=7.8 Hz), 7.22 (2H, m), 5.46 (2H, s), 3.65 (3H, s), 2.65 (2H, q, J=7.6 Hz), 2.30-2.21 (1H, m), 1.08-1.01 (5H, m), 0.80-0.76 (2H, m).

Production Example 101

(305) A mixture of 0.44 g of C14A, 0.33 g of C39A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.48 g of 1-{3-ethyl-2-[1-(3-trifluoromethylphenyl)propylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 101).

(306) ##STR00219##

(307) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.84 (1H, s), 7.74 (1H, d, J=7.8 Hz), 7.59 (1H, d, J=7.8 Hz), 7.48 (1H, d, J=7.8 Hz), 7.45-7.41 (2H, m), 7.23 (1H, dd, J=6.1, 3.1 Hz), 5.27 (2H, s), 3.64 (3H, s), 2.91 (2H, q, J=7.6 Hz), 2.64 (2H, q, J=7.6 Hz), 1.31 (3H, t, J=7.6 Hz), 1.02 (3H, t, J=7.6 Hz).

Production Example 102

(308) A mixture of 0.50 g of C9A, 0.33 g of C39A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.77 g of 1-methyl-4-{3-trifluoromethyl-2-[1-(3-trifluoromethylphenyl)propylideneaminooxymethyl]phenyl}-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 102).

(309) ##STR00220##

(310) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.90 (1H, dd, J=6.8, 2.4 Hz), 7.79 (1H, s), 7.71 (1H, d, J=7.8 Hz), 7.66-7.58 (3H, m), 7.46 (1H, t, J=7.8 Hz), 5.49 (2H, s), 3.58 (3H, s), 2.58 (2H, q, J=7.6 Hz), 0.99 (3H, t, J=7.7 Hz).

Production Example 103

(311) A mixture of 0.30 g of C2A, 0.18 g of C41A, 0.18 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.22 g of 1-[3-chloro-2-(4-chloroindan-1-ylideneaminooxymethyl)phenyl]-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 103).

(312) ##STR00221##

(313) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.58 (1H, d, J=8.0 Hz), 7.48 (1H, d, J=7.6 Hz), 7.41 (1H, t, J=8.0 Hz), 7.30 (2H, dd, J=14.8, 7.9 Hz), 7.17 (1H, t, J=7.8 Hz), 5.40 (2H, s), 3.66 (3H, s), 2.97-2.94 (2H, m), 2.76-2.73 (2H, m).

Production Example 104

(314) A mixture of 0.23 g of C2A, 0.14 g of C45A, 0.14 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.03 g of 1-{3-chloro-2-[1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 104).

(315) ##STR00222##

(316) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.57 (1H, dd, J=8.0, 1.1 Hz), 7.40 (1H, t, J=8.0 Hz), 7.32 (1H, dd, J=8.0, 1.1 Hz), 7.28-7.25 (2H, m), 7.01 (1H, d, J=8.0 Hz), 5.44 (2H, s), 3.59 (3H, s), 2.76-2.74 (4H, m), 2.04 (3H, s), 1.79-1.76 (4H, m).

Production Example 105

(317) A mixture of 0.22 g of C8A, 0.14 g of C45A, 0.14 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.11 g of 1-{3-methoxy-2-[1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 105).

(318) ##STR00223##

(319) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.42 (1H, t, J=8.2 Hz), 7.29-7.26 (2H, m), 7.06 (1H, d, J=8.5 Hz), 7.01 (2H, dt, J=8.1, 1.6 Hz), 5.38 (2H, s), 3.91 (3H, s), 3.56 (3H, s), 2.78-2.73 (4H, m), 2.02 (3H, s), 1.80-1.76 (4H, m).

Production Example 106

(320) A mixture of 0.23 g of C17A, 0.14 g of C45A, 0.14 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.26 g of 1-{3-cyclopropyl-2-[1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 106).

(321) ##STR00224##

(322) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.37 (1H, t, J=7.9 Hz), 7.29-7.28 (2H, m), 7.23-7.19 (2H, m), 7.02 (1H, d, J=8.5 Hz), 5.46 (2H, s), 3.62 (3H, s), 2.78-2.73 (4H, m), 2.29-2.20 (1H, m), 2.07 (3H, s), 1.80-1.75 (4H, m), 1.06-1.01 (2H, m), 0.79-0.75 (2H, m).

Production Example 107

(323) A mixture of 0.22 g of C14A, 0.14 g of C45A, 0.14 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1-{3-ethyl-2-[1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 107).

(324) ##STR00225##

(325) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.41-7.40 (2H, m), 7.29-7.27 (2H, m), 7.23-7.21 (1H, m), 7.02 (1H, d, J=8.5 Hz), 5.26 (2H, s), 3.61 (3H, s), 2.89 (2H, q, J=7.6 Hz), 2.78-2.73 (4H, m), 2.06 (3H, s), 1.80-1.76 (4H, m), 1.29 (3H, t, J=7.6 Hz).

Production Example 108

(326) A mixture of 0.26 g of C5A, 0.14 g of C45A, 0.14 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1-{3-bromo-2-[1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 108).

(327) ##STR00226##

(328) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.76 (1H, dd, J=7.6, 1.1 Hz), 7.37-7.27 (4H, m), 7.01 (1H, d, J=7.8 Hz), 5.44 (2H, s), 3.59 (3H, s), 2.78-2.73 (4H, m), 2.05 (3H, s), 1.79-1.76 (4H, m).

Production Example 109

(329) A mixture of 0.28 g of C11A, 0.19 g of C73A, 0.27 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.20 g of 1-{2-[1-(3-dimethylaminophenyl)ethylideneaminooxymethyl]-3-methylphenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 109).

(330) ##STR00227##

(331) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.37 (2H, d, J=4.8 Hz), 7.23-7.18 (2H, m), 6.96-6.95 (1H, m), 6.88 (1H, d, J=7.8 Hz), 6.73 (1H, dd, J=8.2, 2.8 Hz), 5.25 (2H, s), 3.63 (3H, s), 2.96 (6H, s), 2.55 (3H, s), 2.10 (3H, s).

Production Example 110

(332) A mixture of 0.28 g of C11A, 0.18 g of C101A, 0.26 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.18 g of 1-[2-(1-indan-4-ylethylideneaminooxymethyl)-3-methylphenyl]-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 110).

(333) ##STR00228##

(334) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.37-7.36 (2H, m), 7.24-7.18 (2H, m), 7.13-7.12 (2H, m), 5.26 (2H, s), 3.61 (3H, s), 2.90-2.84 (4H, m), 2.53 (3H, s), 2.07 (3H, s), 2.01-1.94 (2H, m).

Production Example 111

(335) A mixture of 0.35 g of C5A, 0.22 g of C39A, 0.26 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.35 g of 1-{3-bromo-2-[1-(3-trifluoromethylphenyl)propylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 111).

(336) ##STR00229##

(337) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.82 (1H, s), 7.78 (1H, dd, J=6.9, 2.3 Hz), 7.73 (1H, d, J=7.8 Hz), 7.58 (1H, d, J=7.8 Hz), 7.46 (1H, t, J=7.8 Hz), 7.38-7.34 (2H, m), 5.43 (2H, s), 3.63 (3H, s), 2.64 (2H, q, J=7.6 Hz), 1.04 (3H, t, J=7.6 Hz).

Production Example 112

(338) A mixture of 0.34 g of C9A, 0.17 g of C28A, 0.20 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.18 g of 1-{2-[1-(3-chlorophenyl)ethylideneaminooxymethyl]-3-trifluoromethylphenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 112).

(339) ##STR00230##

(340) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.90-7.88 (1H, m), 7.64-7.59 (2H, m), 7.53 (1H, t, J=1.8 Hz), 7.41 (1H, dt, J=7.6, 1.5 Hz), 7.31 (1H, dt, J=8.0, 1.7 Hz), 7.28-7.24 (1H, m), 5.51 (2H, s), 3.58 (3H, s), 2.02 (3H, s).

Production Example 113

(341) A mixture of 0.34 g of C9A, 0.17 g of C21A, 0.20 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.18 g of 1-{2-[1-(3-methoxyphenyl)ethylideneaminooxymethyl]-3-trifluoromethylphenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 113).

(342) ##STR00231##

(343) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.88-7.87 (1H, m), 7.60-7.60 (2H, m), 7.23 (1H, d, J=7.6 Hz), 7.12-7.09 (2H, m), 6.89-6.87 (1H, m), 5.51 (2H, s), 3.81 (3H, s), 3.54 (3H, s), 2.03 (3H, s).

Production Example 114

(344) A mixture of 0.34 g of C9A, 0.22 g of C34A, 0.20 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.25 g of 1-{2-[1-(3-trifluoromethoxyphenyl)ethylideneaminooxymethyl]-3-trifluoromethylphenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 114).

(345) ##STR00232##

(346) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.89 (1H, dd, J=6.1, 3.3 Hz), 7.64-7.59 (2H, m), 7.46 (1H, d, J=8.0 Hz), 7.41 (1H, s), 7.35 (1H, t, J=8.0 Hz), 7.19 (1H, d, J=8.0 Hz), 5.51 (2H, s), 3.57 (3H, s), 2.03 (3H, s).

Production Example 115

(347) A mixture of 0.34 g of C9A, 0.18 g of C30A, 0.20 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.18 g of 1-[2-(1-indan-5-ylethylideneaminooxymethyl)-3-trifluoromethylphenyl]-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 115).

(348) ##STR00233##

(349) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.87 (1H, t, J=4.6 Hz), 7.61-7.59 (2H, m), 7.41 (1H, s), 7.30 (1H, d, J=7.7 Hz), 7.17 (1H, d, J=8.0 Hz), 5.49 (2H, s), 3.53 (3H, s), 2.91-2.86 (4H, m), 2.10-2.04 (2H, m), 2.02 (3H, s).

Production Example 116

(350) A mixture of 0.34 g of C9A, 0.19 g of C45A, 0.20 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.14 g of 1-{2-[1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethylideneaminooxymethyl]-3-trifluoromethylphenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 116).

(351) ##STR00234##

(352) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.87 (1H, t, J=4.7 Hz), 7.59 (2H, d, J=4.4 Hz), 7.27-7.24 (2H, m), 7.01 (1H, d, J=7.8 Hz), 5.48 (2H, s), 3.54 (3H, s), 2.77-2.73 (4H, m), 2.01 (3H, s), 1.79-1.76 (4H, m).

Production Example 117

(353) A mixture of 0.19 g of C9A, 0.19 g of C26A, 0.20 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.21 g of 1-[2-(1-naphthalen-2-ylethylideneaminooxymethyl)-3-trifluoromethyl phenyl]-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 117).

(354) ##STR00235##

(355) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.92 (1H, s), 7.89 (1H, t, J=4.7 Hz), 7.85-7.78 (4H, m), 7.62-7.61 (2H, m), 7.50-7.46 (2H, m), 5.56 (2H, s), 3.49 (3H, s), 2.16 (3H, s).

Production Example 118

(356) A mixture of 0.28 g of C11A, 0.23 g of C102A, 0.20 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.23 g of 1-{2-[1-(3-trifluoromethoxyphenyl)propylideneaminooxymethyl]-3-methylphenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 118).

(357) ##STR00236##

(358) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.49 (1H, d, J=7.8 Hz), 7.45 (1H, s), 7.39-7.34 (3H, m), 7.25-7.17 (2H, m), 5.24 (2H, s), 3.66 (3H, s), 2.62 (2H, q, J=7.6 Hz), 2.55 (3H, s), 1.03 (3H, t, J=7.6 Hz).

Production Example 119

(359) A mixture of 0.30 g of C14A, 0.23 g of C102A, 0.20 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.16 of 1-{3-ethyl-2-[1-(3-trifluoromethoxyphenyl)propylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 119).

(360) ##STR00237##

(361) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.49 (1H, d, J=8.0 Hz), 7.46-7.41 (3H, m), 7.37 (1H, t, J=7.9 Hz), 7.23 (1H, dd, J=6.3, 2.9 Hz), 7.19 (1H, d, J=8.2 Hz), 5.27 (2H, s), 3.64 (3H, s), 2.91 (2H, q, J=7.6 Hz), 2.61 (2H, q, J=7.6 Hz), 1.30 (3H, t, J=7.6 Hz), 1.02 (3H, t, J=7.6 Hz).

Production Example 120

(362) A mixture of 0.31 g of C17A, 0.23 g of C102A, 0.20 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.18 g of 1-{3-cyclopropyl-2-[1-(3-trifluoromethoxyphenyl)propylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 120).

(363) ##STR00238##

(364) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.49 (1H, d, J=7.8 Hz), 7.45 (1H, s), 7.42-7.34 (2H, m), 7.23-7.18 (3H, m), 5.46 (2H, s), 3.65 (3H, s), 2.61 (2H, q, J=7.6 Hz), 2.28-2.21 (1H, m), 1.07-1.01 (5H, m), 0.80-0.76 (2H, m).

Production Example 121

(365) A mixture of 0.35 g of C5A, 0.23 g of C102A, 0.20 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.18 g of 1-{3-bromo-2-[1-(3-trifluoromethoxyphenyl)propylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 121).

(366) ##STR00239##

(367) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.78 (1H, dd, J=6.8, 2.4 Hz), 7.48 (1H, d, J=7.8 Hz), 7.43 (1H, s), 7.38-7.34 (3H, m), 7.19 (1H, d, J=8.2 Hz), 5.43 (2H, s), 3.63 (3H, s), 2.60 (2H, q, J=7.6 Hz), 1.03 (3H, t, J=7.6 Hz).

Production Example 122

(368) A mixture of 0.28 g of C11A, 0.18 g of C103A, 0.26 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.20 g of 1-{3-methyl-2-[1-(3-methylsulfanylphenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 122)

(369) ##STR00240##

(370) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.47 (1H, t, J=1.6 Hz), 7.38-7.37 (2H, m), 7.32 (1H, dt, J=7.3, 1.77 Hz), 7.27-7.21 (3H, m), 5.25 (2H, s), 3.65 (3H, s), 2.55 (3H, s), 2.50 (3H, s), 2.09 (3H, s).

Production Example 123

(371) A mixture of 0.28 g of C11A, 0.24 g of C104A, 0.26 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.30 g of 1-{2-[1-(4-cyclopropyl-3-trifluoromethylphenyl)ethylideneaminooxymethyl]-3-methylphenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 123).

(372) ##STR00241##

(373) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.81 (1H, s), 7.62 (1H, d, J=8.2 Hz), 7.39-7.36 (2H, m), 7.24-7.21 (1H, m), 6.97 (1H, d, J=8.2 Hz), 5.25 (2H, s), 3.66 (3H, s), 2.55 (3H, s), 2.23-2.16 (1H, m), 2.09 (3H, s), 1.07-1.02 (2H, m), 0.79-0.75 (2H, m).

Production Example 124

(374) A mixture of 0.28 g of C14A, 0.18 g of C101A, 0.26 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.21 g of 1-[3-ethyl-2-(1-indan-4-ylethylideneaminooxymethyl)phenyl]-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 124).

(375) ##STR00242##

(376) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.44-7.39 (2H, m), 7.24 (1H, dd, J=6.3, 2.9 Hz), 7.21-7.18 (1H, m), 7.14 (2H, dd, J=8.1, 4.2 Hz), 5.28 (2H, s), 3.59 (3H, s), 2.92-2.86 (6H, m), 2.06 (3H, s), 1.99 (2H, sext, J=7.3 Hz), 1.28 (3H, t, J=7.6 Hz).

Production Example 125

(377) A mixture of 0.30 g of C17A, 0.18 g of C101A, 0.26 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.18 g of 1-[3-cyclopropyl-2-(1-indan-4-ylethylideneaminooxymethyl)phenyl]-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 125).

(378) ##STR00243##

(379) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.38 (1H, t, J=7.8 Hz), 7.25-7.17 (3H, m), 7.15-7.13 (2H, m), 5.49 (2H, s), 3.60 (3H, s), 2.90-2.85 (4H, m), 2.25-2.18 (1H, m), 2.07 (3H, s), 1.98 (2H, sext, J=7.3 Hz), 1.05-1.00 (2H, m), 0.79-0.75 (2H, m).

Production Example 126

(380) A mixture of 0.28 g of C11A, 0.20 g of C105A, 0.26 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.25 g of 1-{3-methyl-2-[1-(5,6,7,8-tetrahydronaphthalen-1-yl)propylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 126).

(381) ##STR00244##

(382) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.40-7.35 (2H, m), 7.25-7.22 (1H, m), 7.10-7.03 (2H, m), 6.91 (1H, dd, J=7.2, 1.5 Hz), 5.18 (2H, s), 3.6 (3H, s), 2.77 (2H, t, J=6.1 Hz), 2.53 (3H, s), 2.57-2.48 (4H, m), 1.79-1.68 (4H, m), 0.89 (3H, t, J=7.6 Hz).

Production Example 127

(383) A mixture of 0.28 g of C11A, 0.19 g of C106A, 0.26 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.25 g of 1-{3-methyl-2-[1-(5,6,7,8-tetrahydronaphthalen-1-yl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 127).

(384) ##STR00245##

(385) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.37-7.36 (2H, m), 7.25-7.22 (1H, m), 7.09-7.02 (2H, m), 6.94 (1H, dd, J=7.1, 1.6 Hz), 5.22 (2H, s), 3.63 (3H, s), 2.77 (2H, t, J=6.2 Hz), 2.56 (2H, t, J=6.1 Hz), 2.53 (3H, s), 2.01 (3H, s), 1.78-1.67 (4H, m).

Production Example 128

(386) A mixture of 0.31 g of C17A, 0.19 g of C106A, 0.27 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.23 g of 1-{3-cyclopropyl-2-[1-(5,6,7,8-tetrahydronaphthalen-1-yl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 128).

(387) ##STR00246##

(388) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.38 (1H, t, J=7.8 Hz), 7.23 (2H, dd, J=7.8, 2.7 Hz), 7.09-7.02 (2H, m), 6.94 (1H, dd, J=7.2, 1.0 Hz), 5.45 (2H, s), 3.61 (3H, s), 2.77 (2H, t, J=6.1 Hz), 2.57 (2H, t, J=6.1 Hz), 2.25-2.18 (1H, m), 2.00 (3H, s), 1.78-1.67 (4H, m), 1.04-0.99 (2H, m), 0.78-0.74 (2H, m).

Production Example 129

(389) A mixture of 0.30 g of C14A, 0.19 g of C106A, 0.26 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.36 g of 1-{3-ethyl-2-[1-(5,6,7,8-tetrahydronaphthalen-1-yl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 129).

(390) ##STR00247##

(391) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.45-7.40 (2H, m), 7.24 (1H, dd, J=6.8, 2.4 Hz), 7.10-7.03 (2H, m), 6.95 (1H, dd, J=7.1, 1.1 Hz), 5.24 (2H, s), 3.61 (3H, s), 2.88 (2H, q, J=7.6 Hz), 2.78 (2H, t, J=6.1 Hz), 2.58 (2H, t, J=6.1 Hz), 2.00 (3H, s), 1.79-1.68 (4H, m), 1.28 (3H, t, J=7.6 Hz).

Production Example 130

(392) A mixture of 0.30 g of C8A, 0.19 g of C106A, 0.26 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.28 g of 1-{3-methoxy-2-[1-(5,6,7,8-tetrahydronaphthalen-1-yl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 130).

(393) ##STR00248##

(394) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.43 (1H, t, J=8.2 Hz), 7.08-7.01 (4H, m), 6.92 (1H, dd, J=7.1, 1.4 Hz), 5.38 (2H, s), 3.89 (3H, s), 3.55 (3H, s), 2.76 (2H, t, J=6.1 Hz), 2.54 (2H, t, J=6.1 Hz), 1.94 (3H, s), 1.77-1.66 (4H, m).

Production Example 131

(395) A mixture of 0.28 g of C11A, 0.16 g of C107A, 0.26 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.24 g of 1-{2-[1-(2,3-dimethylphenyl)ethylideneaminooxymethyl]-3-methylphen yl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 131).

(396) ##STR00249##

(397) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.40-7.36 (2H, m), 7.24 (1H, dd, J=6.0, 3.4 Hz), 7.13-7.05 (2H, m), 6.98 (1H, dd, J=7.4, 1.0 Hz), 5.23 (2H, s), 3.63 (3H, s), 2.53 (3H, s), 2.26 (3H, s), 2.10 (3H, s), 2.03 (3H, s).

Production Example 132

(398) A mixture of 0.30 g of C8A, 0.18 g of C101A, 0.26 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.19 g of 1-[2-(1-indan-4-ylethylideneaminooxymethyl)-3-methoxyphenyl]-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 132).

(399) ##STR00250##

(400) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.42 (1H, t, J=8.2 Hz), 7.19-7.15 (1H, m), 7.14-7.10 (2H, m), 7.06 (1H, d, J=8.2 Hz), 7.02 (1H, d, J=8.0 Hz), 5.41 (2H, s), 3.90 (3H, s), 3.53 (3H, s), 2.89-2.82 (4H, m), 2.01 (3H, s), 1.98-1.93 (2H, m).

Production Example 133

(401) A mixture of 0.28 g of C11A, 0.18 g of C108A, 0.26 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.18 g of 1-{2-[1-(3-chloro-2-methylphenyl)ethylideneaminooxymethyl]-3-methylphenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 133).

(402) ##STR00251##

(403) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.41-7.36 (2H, m), 7.33 (1H, dd, J=7.8, 1.4 Hz), 7.24 (1H, dd, J=6.0, 3.2 Hz), 7.11 (1H, t, J=7.8 Hz), 7.04 (1H, dd, J=7.7, 1.3 Hz), 5.23 (2H, s), 3.63 (3H, s), 2.53 (3H, s), 2.23 (3H, s), 2.02 (3H, s).

Production Example 134

(404) A mixture of 0.28 g of C11A, 0.22 g of C109A, 0.26 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.31 g of 1-{2-[1-(2,2-difluorobenzo[1,3]dioxan-4-yl)ethylideneaminooxymethyl]-3-methylphenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 134).

(405) ##STR00252##

(406) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.39 (2H, d, J=5.3 Hz), 7.27-7.20 (2H, m), 7.06-7.00 (2H, m), 5.27 (2H, s), 3.69 (3H, s), 2.56 (3H, s), 2.15 (3H, s).

Production Example 135

(407) A mixture of 0.30 g of C8A, 0.22 g of C109A, 0.26 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.37 g of 1-{2-[1-(2,2-difluorobenzo[1,3]dioxan-4-yl)ethylideneaminooxymethyl]-3-methoxyphenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 135).

(408) ##STR00253##

(409) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.45 (1H, t, J=8.24 Hz), 7.24 (1H, dd, J=7.4, 4.5 Hz), 7.08 (1H, d, J=8.0 Hz), 7.05-7.00 (3H, m), 5.40 (2H, s), 3.93 (3H, s), 3.63 (3H, s), 2.10 (3H, s).

Production Example 136

(410) A mixture of 0.28 g of C11A, 0.21 g of C110A, 0.26 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.25 g of 1-{2-[1-(7-methoxyindan-4-yl)ethylideneaminooxymethyl]-3-methylphenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 136).

(411) ##STR00254##

(412) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.37-7.35 (2H, m), 7.25-7.20 (1H, m), 7.15 (1H, d, J=8.5 Hz), 6.66 (1H, d, J=8.5 Hz), 5.24 (2H, s), 3.82 (3H, s), 3.63 (3H, s), 2.88 (2H, t, J=7.4 Hz), 2.82 (2H, t, J=7.4 Hz), 2.53 (3H, s), 2.06 (3H, s), 2.02-1.94 (2H, m).

Production Example 137

(413) A mixture of 0.30 g of C14A, 0.21 g of C110A, 0.26 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.13 g of 1-{3-ethyl-2-[1-(7-methoxyindan-4-yl)ethylideneaminooxymethyl]phen yl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 137).

(414) ##STR00255##

(415) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.41-7.39 (2H, m), 7.23 (1H, dd, J=6.1, 3.1 Hz), 7.15 (1H, d, J=8.2 Hz), 6.66 (1H, d, J=8.5 Hz), 5.26 (2H, s), 3.82 (3H, s), 3.60 (3H, s), 2.92-2.81 (6H, m), 2.04 (3H, s), 2.03-1.95 (2H, m), 1.32-1.24 (3H, t, J=7.5 Hz).

Production Example 138

(416) A mixture of 0.31 g of C17A, 0.21 g of C110A, 0.26 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.24 g of 1-{3-cyclopropyl-2-[1-(7-methoxyindan-4-yl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 138).

(417) ##STR00256##

(418) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.37 (1H, t, J=7.9 Hz), 7.22 (2H, dd, J=7.7, 1.9 Hz), 7.15 (1H, d, J=8.5 Hz), 6.65 (1H, d, J=8.5 Hz), 5.47 (2H, s), 3.82 (3H, s), 3.60 (3H, s), 2.89 (2H, t, J=7.5 Hz), 2.82 (2H, t, J=7.5 Hz), 2.25-2.18 (1H, m), 2.05 (3H, s), 2.02-1.94 (2H, m), 1.04-0.99 (2H, m), 0.78-0.74 (2H, m).

Production Example 139

(419) A mixture of 0.28 g of C11A, 0.23 g of C111A, 0.26 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.38 g of 1-{2-[1-(4-methoxy-3-trifluoromethylphenyl)ethylideneaminooxymethy 1]-3-methylphenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 139).

(420) ##STR00257##

(421) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.80 (1H, d, J=2.1 Hz), 7.72 (1H, dd, J=8.7, 2.1 Hz), 7.38 (2H, d, J=5.3 Hz), 7.24-7.20 (1H, m), 6.96 (1H, d, J 25=8.7 Hz), 5.24 (2H, s), 3.91 (3H, s), 3.67 (3H, s), 2.55 (3H, s), 2.09 (3H, s).

Production Example 140

(422) A mixture of 0.30 g of C14A, 0.23 g of C111A, 0.26 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.39 g of 1-{3-ethyl-2-[1-(4-methoxy-3-trifluoromethylphenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 140).

(423) ##STR00258##

(424) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.80 (1H, s), 7.71 (1H, dd, J=8.6, 1.7 Hz), 7.43-7.41 (2H, m), 7.22 (1H, dd, J=6.0, 3.2 Hz), 6.96 (1H, d, J=8.9 Hz), 5.27 (2H, s), 3.92 (3H, s), 3.65 (3H, s), 2.90 (2H, q, J=7.6 Hz), 2.08 (3H, s), 1.30 (3H, t, J=7.6 Hz).

Production Example 141

(425) A mixture of 0.28 g of C17A, 0.19 g of C111A, 0.26 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.40 g of 1-{3-cyclopropyl-2-[1-(4-methoxy-3-trifluoromethylphenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 141).

(426) ##STR00259##

(427) .sup.1H-NMR (CDCl.sub.3) (ppm): 7.80 (1H, d, J=2.1 Hz), 7.71 (1H, dd, J=8.7, 2.3 Hz), 7.39 (1H, t, J=7.9 Hz), 7.24-7.20 (2H, m), 6.96 (1H, d, J=8.7 Hz), 5.47 (2H, s), 3.91 (3H, s), 3.65 (3H, s), 2.28-2.21 (1H, m), 2.08 (3H, s), 1.08-1.03 (2H, m), 0.80-0.76 (2H, m).

Production Example 142

(428) A mixture of 0.30 g of C2A, 0.17 g of C101A, 0.26 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.28 g of 1-[3-chloro-2-(1-indan-4-ylethylideneaminooxymethyl)phenyl]-4-meth yl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 142).

(429) ##STR00260##

(430) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.59-7.56 (1H, m), 7.41 (1H, t, J=7.9 Hz), 7.35-7.32 (1H, m), 7.19-7.17 (1H, m), 7.12-7.11 (2H, m), 5.48 (2H, s), 3.56 (3H, s), 2.87 (2H, t, J=7.5 Hz), 2.82 (2H, t, J=7.5 Hz), 2.03 (3H, s), 2.00-1.92 (2H, m).

Production Example 143

(431) A mixture of 0.28 g of C11A, 0.21 g of C112A, 0.26 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.25 g of 1-{3-methyl-2-[1-(2-methy 3-difluoromethylphenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 143).

(432) ##STR00261##

(433) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.60 (1H, d, J=7.3 Hz), 7.41-7.37 (2H, m), 7.31-7.23 (3H, m), 5.25 (2H, s), 3.62 (3H, s), 2.53 (3H, s), 2.30 (3H, d, J=1.6 Hz), 2.03 (3H, s).

Production Example 144

(434) A mixture of 0.28 g of C11A, 0.19 g of C113A, 0.26 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.20 g of 1-{2-[1-(3-cyclopropyl-2-methylphenyl)ethylideneaminooxymethyl]-3-methylphenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 144).

(435) ##STR00262##

(436) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.41-7.36 (2H, m), 7.26-7.23 (1H, m), 7.09 (1H, t, J=7.6 Hz), 7.00 (1H, d, J=7.3 Hz), 6.98 (1H, d, J=7.6 Hz), 5.23 (2H, s), 3.63 (3H, s), 2.54 (3H, s), 2.28 (3H, s), 2.03 (3H, s), 1.89-1.82 (1H, m), 0.94-0.89 (2H, m), 0.63-0.59 (2H, m).

Production Example 145

(437) A mixture of 0.28 g of C11A, 0.18 g of C114A, 0.26 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.18 g of 1-{2-[1-(3-ethyl-2-methylphenyl)ethylideneaminooxymethyl]-3-methyl phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 145).

(438) ##STR00263##

(439) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.38-7.36 (2H, m), 7.26-7.23 (1H, m), 7.15-7.10 (2H, m), 6.97 (1H, dd, J=6.5, 2.4 Hz), 5.23 (2H, s), 3.62 (3H, s), 2.63 (2H, q, J=7.6 Hz), 2.53 (3H, s), 2.14 (3H, s), 2.02 (3H, s), 1.19 (3H, t, J=7.6 Hz).

Production Example 146

(440) A mixture of 0.28 g of C11A, 0.16 g of C115A, 0.26 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.22 g of 1-{2-[1-(2,5-dimethylphenyl)ethylideneaminooxymethyl]-3-methylphenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 146).

(441) ##STR00264##

(442) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.40-7.35 (2H, m), 7.25-7.22 (1H, m), 7.06-7.01 (2H, m), 6.97 (1H, s), 5.23 (2H, s), 3.62 (3H, s), 2.53 (3H, s), 2.30 (3H, s), 2.17 (3H, s), 2.03 (3H, s).

Production Example 147

(443) A mixture of 0.05 g of C11A, 0.06 g of N-hydroxy-3-trifluoromethylthiobenzimidic acid methyl ester, 0.26 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated.

(444) The obtained residue was subjected to silica gel column chromatography to obtain 0.07 g of N-[2-methyl-6-(4-methoxy-5-oxo-4,5-dihydrotetrazol-1-yl)benzoyloxy]-3-trifluoromethylthiobenzimidic acid methyl ester (hereinafter referred to as the present compound 147).

(445) ##STR00265##

(446) MS, m/z: 438 (M+1).

Production Example 148

(447) A mixture of 0.28 g of C11A, 0.22 g of C117A, 0.26 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.32 g of 1-{2-[1-(2-fluoro-3-trifluoromethylphenyl)ethylideneaminooxymethyl]-3-methylphenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 148).

(448) ##STR00266##

(449) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.62-7.57 (2H, m), 7.40-7.36 (2H, m), 7.25-7.19 (2H, m), 5.26 (2H, s), 3.67 (3H, s), 2.54 (3H, s), 2.14 (3H, d, J=3.0 Hz).

Production Example 149

(450) A mixture of 0.56 g of C11A, 0.27 g of acetophenone oxime, 0.52 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated.

(451) The obtained residue was subjected to silica gel column chromatography to obtain 0.47 g of 1-[2-(1-phenylethylideneaminooxymethyl)-3-methylphenyl]-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 149).

(452) ##STR00267##

(453) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.59-7.56 (2H, m), 7.38-7.33 (5H, m), 7.25-7.21 (1H, m), 5.26 (2H, s), 3.63 (3H, s), 2.55 (3H, s), 2.11 (3H, s).

Production Example 150

(454) A mixture of 0.28 g of C11A, 0.21 g of C118A, 0.26 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.08 g of 1-[2-(1-biphenyl-2-ylethylideneaminooxymethyl)-3-methylphenyl]-4-m ethyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 150).

(455) ##STR00268##

(456) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.44-7.23 (12H, m), 5.21 (2H, s), 3.64 (3H, s), 2.51 (3H, s), 1.50 (3H, s).

Production Example 151

(457) A mixture of 0.33 g of C16A, 0.18 g of C101A, 0.26 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.18 g of 1-[3-difluoromethoxy-2-(1-indan-4-ylethylideneaminooxymethyl)phenyl]-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 151).

(458) ##STR00269##

(459) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.50 (1H, t, J=8.1 Hz), 7.34 (2H, t, J=8.2 Hz), 7.19 (1H, d, J=6.6 Hz), 7.14-7.08 (2H, m), 6.56 (1H, t, J=73.5 Hz), 5.40 (2H, s), 3.56 (3H, s), 2.87 (2H, t, J=7.4 Hz), 2.80 (2H, t, J=7.3 Hz), 2.01 (3H, s), 1.98-1.92 (2H, m).

Production Example 152

(460) A mixture of 0.28 g of C11A, 0.18 g of C119A, 0.26 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.11 g of 1-{2-[1-(2,3-dihydrobenzofuran-4-yl)ethylideneaminooxymethyl]-3-methylphenyl]-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 152).

(461) ##STR00270##

(462) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.37-7.36 (2H, m), 7.25-7.22 (1H, m), 7.10 (1H, t, J=7.7 Hz), 6.89 (1H, d, J=7.9 Hz), 6.76 (1H, d, J=7.9 Hz), 5.26 (2H, s), 4.48 (2H, t, J=8.8 Hz), 3.63 (3H, s), 3.12 (2H, t, J=8.8 Hz), 2.52 (3H, s), 2.09 (3H, s).

Production Example 153

(463) A mixture of 0.30 g of C14A, 0.18 g of C119A, 0.26 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.13 g of 1-{2-[1-(2,3-dihydrobenzofuran-4-yl)ethylideneaminooxymethyl]-3-ethylphenyl]-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 153).

(464) ##STR00271##

(465) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.44-7.39 (2H, m), 7.23 (1H, dd, J=6.4, 2.8 Hz), 7.11 (1H, t, J=7.9 Hz), 6.89 (1H, d, J=8.0 Hz), 6.76 (1H, d, J=7.8 Hz), 5.29 (2H, s), 4.49 (2H, t, J=8.8 Hz), 3.59 (3H, s), 3.15 (2H, t, J=8.8 Hz), 2.88 (2H, q, J=7.5 Hz), 2.07 (3H, s), 1.28 (3H, t, J=7.5 Hz).

Production Example 154

(466) A mixture of 0.31 g of C17A, 0.18 g of C119A, 0.26 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.13 g of 1-{3-cyclopropyl-2-[1-(2,3-dihydrobenzofuran-4-yl)ethylideneaminooxymethyl]phenyl]-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 154).

(467) ##STR00272##

(468) .sup.1H-NMR (CDCl.sub.3) δ (ppm): 7.38 (1H, t, J=7.9 Hz), 7.23 (2H, dd, J=7.8, 2.3 Hz), 7.11 (1H, t, J=7.8 Hz), 6.90 (1H, d, J=7.8 Hz), 6.76 (1H, d, J=7.8 Hz), 5.50 (2H, s), 4.48 (2H, t, J=8.8 Hz), 3.60 (3H, s), 3.14 (2H, t, J=8.8 Hz), 2.24-2.17 (1H, m), 2.08 (3H, s), 1.05-1.00 (2H, m), 0.78-0.74 (2H, m).

Production Example 155

(469) A mixture of 0.28 g of C11A, 0.23 g of C120A, 0.26 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.26 g of 1-[2-(1-biphenyl-3-ylethylideneaminooxymethyl)-3-methylphenyl]-4-m ethyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 155).

(470) ##STR00273##

(471) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.37-7.27 (6H, m), 7.25-7.24 (1H, m), 7.21 (1H, dd, J=6.2, 3.0 Hz), 7.11 (1H, t, J=7.3 Hz), 7.01-6.95 (3H, m), 5.23 (2H, s), 3.65 (3H, s), 2.52 (3H, s), 2.07 (3H, s).

Production Example 156

(472) A mixture of 0.12 g of C11A, 0.12 g of C121A, 0.10 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1-{2-[1-(4-phenyl-3-trifluoromethylphenyl)ethylideneaminooxymethyl]-3-methylphenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 156).

(473) ##STR00274##

(474) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.95 (1H, d, J=1.8 Hz), 7.75 (1H, dd, J=8.0, 1.4 Hz), 7.41-7.39 (5H, m), 7.32-7.29 (3H, m), 7.23 (1H, t, J=4.6 Hz), 5.29 (2H, s), 3.68 (3H, s), 2.57 (3H, s), 2.16 (3H, s).

Production Example 157

(475) A mixture of 0.67 g of C9A, 0.41 g of C119A, 0.55 g of potassium carbonate, and 15 ml of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.17 g of 1-{3-trifluoromethyl-2-[1-(2,3-dihydrobenzofuran-4-yl)ethylideneaminooxymethyl]phenyl]-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 157).

(476) ##STR00275##

(477) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.88-7.86 (1H, m), 7.63-7.60 (2H, m), 7.10 (1H, t, J=7.9 Hz), 6.88 (1H, d, J=7.9 Hz), 6.76 (1H, d, J=8.0 Hz), 5.51 (2H, s), 4.46 (2H, t, J=8.8 Hz), 3.54 (3H, s), 3.09 (2H, t, J=8.7 Hz), 2.01 (3H, s).

Production Example 158

(478) A mixture of 0.34 g of C11A, 0.21 g of C116A, 0.55 g of potassium carbonate, and 15 ml of acetonitrile was stirred at 70° C. for 24 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.10 g of 1-{3-trifluoromethyl-2-[1-(2,2-dimethyl-2,3-dihydrobenzofuran-4-yl)ethylideneaminooxymethyl]phenyl]-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 158).

(479) ##STR00276##

(480) .sup.1H-NMR (CDCl.sub.3) δ: 7.37-7.34 (2H, m), 7.25-7.22 (1H, m), 7.09 (1H, t, J=7.8 Hz), 6.87 (1H, dd, J=7.9, 0.8 Hz), 6.69 (1H, d, J=8.0 Hz), 5.25 (2H, s), 3.65 (3H, s), 2.84 (2H, s), 2.52 (3H, s), 2.08 (3H, s), 1.40 (6H, s).

Production Example 159

(481) A mixture of 0.56 g of C11A, 0.36 g of C92A, 0.55 g of potassium carbonate, and 15 ml of acetonitrile was stirred at 70° C. for 24 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.30 g of 1-[2-(1-benzo[1,3]dioxol-4-ylethylideneaminooxymethyl)-3-methylphenyl]-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 159).

(482) ##STR00277##

(483) .sup.1H-NMR (CDCl.sub.3) δ: 7.38-7.36 (2H, m), 7.22 (1H, t, J=4.9 Hz), 7.04-7.00 (1H, m), 6.80-6.79 (2H, m), 5.96 (2H, s), 5.25 (2H, s), 3.66 (3H, s), 2.55 (3H, s), 2.13 (3H, s).

Production Example 201

(484) A mixture of 0.42 g of C11A, 0.28 g of C201A, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.14 g of 1-[2-(1-cyclohexylethylideneaminooxymethyl)-3-methylphenyl]-4-meth yl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 201).

(485) ##STR00278##

(486) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.35-7.32 (2H, m), 7.21-7.17 (1H, m), 5.07 (2H, s), 3.69 (3H, s), 2.50 (3H, s), 2.07-2.00 (1H, m), 1.80-1.63 (5H, m), 1.64 (3H, s), 1.30-1.10 (5H, m).

Production Example 202

(487) A mixture of 0.42 g of C11A, 0.21 g of C202A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.27 g of 1-[2-(1-cyclohex-1-enylethylideneaminooxymethyl)-3-methylphenyl]-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 202).

(488) ##STR00279##

(489) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.37-7.34 (2H, m), 7.23-7.17 (1H, m), 6.07-6.05 (1H, m), 5.13 (2H, s), 3.69 (3H, s), 2.51 (3H, s), 2.17-2.11 (4H, m), 1.81 (3H, s), 1.61-1.55 (4H, m).

Production Example 203

(490) A mixture of 0.84 g of C11A, 0.34 g of C203A, 0.56 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.54 g of 1-[2-(1,2-dimethylbutan-2-enylideneaminooxymethyl)-3-methylphenyl]-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 203).

(491) ##STR00280##

(492) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.36-7.35 (2H, m), 7.22-7.19 (1H, m), 5.91-5.85 (1H, m), 5.15 (2H, s), 3.69 (3H, s), 2.52 (3H, s), 1.82 (3H, s), 1.73 (3H, bs), 1.72 (3H, bs).

Production Example 204

(493) A mixture of 0.84 g of C11A, 0.34 g of C204A, 0.56 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.53 g of 1-[2-(1,4-dimethylpentane-2-enylideneaminooxymethyl)-3-methylphenyl]-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 204).

(494) ##STR00281##

(495) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.37-7.35 (2H, m), 7.22-7.20 (1H, m), 5.97-5.96 (2H, m), 5.11 (2H, s), 3.69 (3H, s), 2.50 (3H, s), 2.43-2.35 (1H, m), 1.81 (3H, s), 1.02 (6H, d, J=6.8 Hz).

Production Example 205

(496) A mixture of 0.30 g of C11A, 0.16 g of 4-phenylbut-3-en-2-one oxime, 0.18 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.27 g of 1-methyl-4-[3-methyl-2-(1-methyl-3-phenylallylideneaminooxymethyl)phenyl]-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 205).

(497) ##STR00282##

(498) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.45-7.22 (8H, m), 6.80 (1H, d, J=16.5 Hz), 6.72 (1H, d, J=16.5 Hz), 5.19 (2H, s), 3.70 (3H, s), 2.53 (3H, s), 1.95 (3H, s).

Production Example 206

(499) A mixture of C11A, 4-(4-chlorophenyl)but-3-en-2-one oxime, potassium carbonate, and acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1-{2-[3-(4-chlorophenyl)-1-methylallylideneaminooxymethyl)-3-methylphenyl]-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 206).

(500) ##STR00283##

(501) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.39-7.35 (4H, m), 7.31-7.28 (2H, m), 7.25-7.21 (1H, m), 6.74 (1H, d, J=16.6 Hz), 6.68 (1H, d, J=16.6 Hz), 5.19 (2H, s), 3.70 (3H, s), 2.52 (3H, s), 1.93 (3H, s).

Production Example 207

(502) A mixture of C8A, 4-(4-chlorophenyl)but-3-en-2-one oxime, potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1-{2-[3-(4-chlorophenyl)-1-methylallylideneaminooxymethyl)-3-methoxyphenyl]-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 207).

(503) ##STR00284##

(504) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.44 (1H, t, J=8.2 Hz), 7.37-7.28 (4H, m), 7.07 (1H, d, J=8.0 Hz), 7.02 (1H, d, J=8.0 Hz), 6.69 (1H, d, J=16.4 Hz), 6.66 (1H, d, J=16.4 Hz), 5.33 (2H, s), 3.92 (3H, s), 3.67 (3H, s), 1.88 (3H, s).

Production Example 208

(505) A mixture of 0.30 g of C11A, 0.23 g of 4-(2,6-dichlorophenyl)but-3-en-2-one oxime, 0.18 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.09 g of 1-{2-[3-(2,6-dichlorophenyl)-1-methylallylideneaminooxymethyl)-3-m ethylphenyl]-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 208).

(506) ##STR00285##

(507) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.39-7.37 (2H, m), 7.32 (2H, d, J=8.0 Hz), 7.23 (1H, dd, J=5.5, 3.4 Hz), 7.11 (1H, t, J=8.0 Hz), 6.84 (1H, d, J=16.7 Hz), 6.76 (1H, d, J=16.7 Hz), 5.20 (2H, s), 3.70 (3H, s), 2.53 (3H, s), 1.98 (3H, s).

Production Example 209

(508) A mixture of 0.42 g of C11A, 0.24 g of C208A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.30 g of pentane-2,3-dione-3-{O-[2-methyl-6-(4-methyl-5-oxo-4,5-dihydrotetrazol-1-yl)benzyl]oxime}(hereinafter referred to as the present compound 209).

(509) ##STR00286##

(510) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.40-7.39 (2H, m), 7.24-7.22 (1H, m), 5.29 (2H, s), 3.71 (3H, s), 2.83 (2H, q, J=7.6 Hz), 2.53 (3H, s), 1.81 (3H, s), 1.03 (3H, t, J=7.6 Hz).

Production Example 210

(511) A mixture of 0.42 g of C11A, 0.24 g of C210A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.24 g of pentane-2,3,4-trione-2-{O-[2-methyl-6-(4-methyl-5-oxo-4,5-dihydrotetrazol-1-yl)benzyl]oxime}-4-(O-methyloxime) (hereinafter referred to as the present compound 210).

(512) ##STR00287##

(513) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.4-7.3 (2H, m), 7.2-7.3 (1H, m), 5.29 (2H, s), 3.98 (3H, s), 3.70 (3H, s), 2.51 (3H, s), 1.94 (3H, s), 1.91 (3H, s).

Production Example 211

(514) A mixture of 0.28 g of C11A, 0.19 g of C211A, 0.18 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.27 g of pentane-2,3,4-trione-2-{O-[2-methyl-6-(4-methyl-5-oxo-4,5-dihydrotetrazol-1-yl)benzyl]oxime}-3,4-bis-(O-methyloxime): A (hereinafter referred to as the present compound 211)

(515) ##STR00288##

(516) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.39-7.33 (2H, m), 7.21-7.18 (1H, m), 5.19 (2H, s), 3.92 (3H, s), 3.91 (3H, s), 3.71 (3H, s), 2.48 (3H, s), 1.91 (3H, s), 1.80 (3H, s).

Production Example 212

(517) A mixture of 0.28 g of C11A, 0.19 g of C211B, 0.18 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.28 g of pentane-2,3,4-trione-2-{O-[2-methyl-6-(4-methyl-5-oxo-4,5-dihydrotetrazol-1-yl)benzyl]oxime}-3,4-bis-(O-methyloxime): B (hereinafter referred to as the present compound 212).

(518) ##STR00289##

(519) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.39-7.34 (2H, m), 7.23-7.21 (1H, m), 5.18 (2H, s), 3.93 (3H, s), 3.89 (3H, s), 3.69 (3H, s), 2.50 (3H, s), 2.00 (3H, s), 1.84 (3H, s).

Production Example 213

(520) A mixture of C11A, 1-(4-chlorophenyl)propane-1,2-dione-1-(O-methyloxime)-2-oxime, potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1-(4-chlorophenyl)propane-1,2-dione-2-{O-[2-methyl-6-(4-methyl-5-oxo-4,5-dihydrotetrazol-1-yl)benzyl]oxime}-1-(O-methyloxime) (hereinafter referred to as the present compound 213).

(521) ##STR00290##

(522) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.43-7.34 (2.0H, m), 7.30-7.17 (4.0H, m), 7.01-6.99 (1.0H, m), 5.23 (0.5H, s), 5.06 (1.5H, s), 3.97 (0.8H, s), 3.88 (2.2H, s), 3.69 (2.2H, s), 3.67 (0.8H, s), 2.47 (0.8H, s), 2.23 (2.2H, s), 1.99 (2.2H, s), 1.93 (0.8H, s).

Production Example 214

(523) A mixture of C2A, 1-(4-chlorophenyl)propane-1,2-dione-1-(O-methyloxime)-2-oxime, potassium carbonate, and acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1-(4-chlorophenyl)propane-1,2-dione-2-{O-[2-chloro-6-(4-methyl-5-oxo-4,5-dihydrotetrazol-1-yl)benzyl]oxime}-1-(O-methyloxime) (hereinafter referred to as the present compound 214).

(524) ##STR00291##

(525) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.58-7.49 (1.0H, m), 7.47-7.34 (2.0H, m), 7.31-7.23 (3.0H, m), 7.03-7.00 (1.0H, m), 5.43 (0.5H, s), 5.27 (1.5H, s), 3.97 (0.8H, s), 3.89 (2.2H, s), 3.68 (2.2H, s), 3.63 (0.8H, s), 1.97 (2.2H, s), 1.90 (0.8H, s).

Production Example 215

(526) A mixture of C8A, 1-phenylpropane-1,2-dione-1-(O-methyloxime)-2-oxime, potassium carbonate, and acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1-phenylpropane-1,2-dion-2-{O-[2-methoxy-6-(4-methyl-5-oxo-4,5-dihydrotetrazol-1-yl)benzyl]oxime}-1-(O-methyloxime) (hereinafter referred to as the present compound 215).

(527) ##STR00292##

(528) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.51-7.47 (1.0H, m), 7.45-7.40 (1.0H, m), 7.34-7.27 (3.0H, m), 7.11-7.09 (1.0H, m), 7.04 (1.0H, m), 7.01-6.98 (1H, m), 5.37 (0.9H, s), 5.21 (1.1H, s), 3.97 (1.3H, s), 3.88 (1.7H, s), 3.84 (1.3H, s), 3.70 (1.7H, s), 3.67 (1.7H, s), 3.61 (1.3H, s), 1.95 (1.7H, s), 1.89 (1.3H, s).

Production Example 216

(529) A mixture of 0.28 g of C11A, 0.21 g of C215A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 1-(2-{1-[2-(4-chlorophenyl)cyclopropyl]ethylideneaminooxymethyl}-3-methylphenyl)-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 216).

(530) ##STR00293##

(531) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.37-7.35 (2H, m), 7.24-7.19 (3H, m), 7.01-6.98 (2H, m), 5.06 (2H, s), 3.67 (3H, s), 2.50 (3H, s), 2.09-2.06 (1H, m), 1.71-1.67 (1H, m), 1.66 (3H, s), 1.36-1.30 (1H, m), 1.11-1.06 (1H, m).

Production Example 217

(532) A mixture of 0.28 g of C11A, 0.24 g of C216A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.22 g of 1-(2-{1-[2-(2,6-dichlorophenyl)cyclopropyl]ethylideneaminooxymethy 1}-3-methylphenyl)-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 217).

(533) ##STR00294##

(534) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.36-7.35 (2H, m), 7.25 (2H, d, J=8.2 Hz), 7.21 (1H, t, J=4.6 Hz), 7.08 (1H, t, J=8.0 Hz), 5.10 (2H, s), 3.70 (3H, s), 2.52 (3H, s), 2.07-2.00 (1H, m), 1.80-1.75 (1H, m), 1.73 (3H, s), 1.53-1.48 (1H, m), 1.21-1.16 (1H, m).

Production Example 218

(535) A mixture of 0.28 g of C11A, C214A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.16 g of 1-{2-[1-(2-phenylcyclopropyl)ethylideneaminooxymethyl]-3-methylphenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 218).

(536) ##STR00295##

(537) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.37-7.35 (2H, m), 7.27-7.13 (4H, m), 7.08-7.06 (2H, m), 5.07 (2H, s), 3.66 (3H, s), 2.50 (3H, s), 2.12-2.08 (1H, m), 1.75-1.70 (1H, m), 1.66 (3H, s), 1.36-1.31 (1H, m), 1.15-1.10 (1H, m).

Production Example 219

(538) A mixture of 0.56 g of C11A, 0.48 g of C205A, 0.42 g of potassium carbonate, and 20 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.61 g of 1-methyl-4-(3-methyl-2-{1-[1-(3-trifluoromethylphenyl)cyclopropyl]ethylideneaminooxymethyl]phenyl}1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 219).

(539) ##STR00296##

(540) .sup.1H-NMR (CDCl.sub.3) δ: 7.46-7.43 (2H, m), 7.38-7.32 (4H, m), 7.20 (1H, dd, J=7.0, 2.0 Hz), 5.10 (2H, s), 3.69 (3H, s), 2.45 (3H, s), 1.61 (4H, s), 1.22 (2H, dd, J=6.6, 4.5 Hz), 0.98 (2H, dd, J=6.7, 4.6 Hz).

Production Example 251

(541) A mixture of 0.42 g of C11A, 0.20 g of C251A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.16 g of 1-methyl-4-[3-methyl-2-(1-pyridin-3-ylethylideneaminooxymethyl)phenyl]-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 251).

(542) ##STR00297##

(543) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.78 (1H, d, J=2.2 Hz), 8.56 (1H, dd, J=4.8, 1.5 Hz), 7.87 (1H, dt, J=8.1, 1.9 Hz), 7.38-7.35 (2H, m), 7.28-7.21 (2H, m), 5.27 (2H, s), 3.66 (3H, s), 2.55 (3H, s), 2.12 (3H, s).

Production Example 252

(544) A mixture of 0.50 g of C11A, 0.20 g of C252A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.37 g of 1-methyl-4-[3-methyl-2-(1-pyridin-2-ylethylideneaminooxymethyl)phenyl]-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 252).

(545) ##STR00298##

(546) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.55 (1H, dq, J=4.8, 1.0 Hz), 7.81 (1H, dt, J=8.1, 1.0 Hz), 7.64 (1H, td, J=7.8, 1.9 Hz), 7.39-7.38 (2H, m), 7.25-7.20 (2H, m), 5.28 (2H, s), 3.68 (3H, s), 2.56 (3H, s), 2.21 (3H, s).

Production Example 253

(547) A mixture of 0.28 g of C11A, 0.20 g of C253A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.18 g of 1-methyl-4-{3-methyl-2-[1-(6-trifluoromethylpyridin-2-yl)ethylideneaminooxymethyl]phenyl}-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 253).

(548) ##STR00299##

(549) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.01 (1H, d, J=7.9 Hz), 7.79 (1H, t, J=7.9 Hz), 7.59 (1H, dd, J=7.7, 0.7 Hz), 7.40-7.37 (2H, m), 7.25-7.21 (1H, m), 5.28 (2H, s), 3.70 (3H, s), 2.56 (3H, s), 2.23 (3H, s).

Production Example 254

(550) A mixture of 0.56 g of C11A, 0.28 g of C254A, 0.56 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.31 g of 1-methyl-4-{3-methyl-2-[1-(1-methyl-1H-pyrrol-3-yl)ethylideneaminooxymethyl]phenyl}-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 254).

(551) ##STR00300##

(552) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.37-7.34 (2.0H, m), 7.30-7.27 (0.6H, m), 7.24-7.19 (1.0H, m), 6.80 (0.4H, t, J=2.1 Hz), 6.52 (0.4H, t, J=2.5 Hz), 6.50 (0.6H, t, J=2.5 Hz), 6.34 (0.4H, dd, J=2.8, 1.8 Hz), 6.32 (0.6H, dd, J=2.9, 1.7 Hz), 5.19 (1.2H, s), 5.14 (0.8H, s), 3.66 (1.2H, s), 3.62 (3.0H, s), 3.58 (1.8H, s), 2.54 (1.2H, s), 2.53 (1.8H, s), 2.09 (1.8H, s), 1.98 (1.2H, s).

Production Example 255

(553) A mixture of 0.42 g of C11A, 0.21 g of C255A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.29 g of 1-methyl-4-{3-methyl-2-[1-(1-methyl-1H-pyrrol-2-yl)ethylideneaminooxymethyl]phenyl}-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 255).

(554) ##STR00301##

(555) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.35-7.32 (2H, m), 7.22-7.19 (1H, m), 6.58-6.56 (1H, m), 6.35-6.33 (1H, m), 6.05-6.03 (1H, m), 5.20 (2H, s), 3.64 (3H, s), 3.58 (3H, s), 2.51 (3H, s), 2.04 (3H, s).

Production Example 256

(556) A mixture of 0.42 g of C11A, 0.23 g of C256A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.07 g of 1-methyl-4-{3-methyl-2-[1-(4-methyl-2-thienyl)ethylideneaminooxymethyl]phenyl}-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 256).

(557) ##STR00302##

(558) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.36-7.34 (2H, m), 7.21 (1H, t, J=4.4 Hz), 6.96 (1H, s), 6.80 (1H, s), 5.19 (2H, s), 3.66 (3H, s), 2.53 (3H, s), 2.20 (3H, s), 2.07 (3H, s).

Production Example 257

(559) A mixture of 0.42 g of C11A, 0.21 g of C257A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.17 g of 1-methyl-4-{3-methyl-2-[1-(2-thienyl)ethylideneaminooxymethyl]phen yl}-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 257).

(560) ##STR00303##

(561) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.38-7.37 (2H, m), 7.25 (1H, dd, J=0.8, 5.6 Hz), 7.22 (1H, dd, J=4.4, 4.4 Hz), 7.16 (1H, dd, J=1.2, 3.6 Hz), 6.98 (1H, dd, J=3.6, 4.8 Hz), 5.21 (2H, s), 3.68 (3H, s), 2.55 (3H, s), 2.12 (3H, s).

Production Example 258

(562) A mixture of 0.42 g of C11A, 0.23 g of C258A, 0.28 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.40 g of 1-methyl-4-{3-methyl-2-[1-(3-methyl-2-thienyl)ethylideneaminooxymethyl]phenyl}-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 258).

(563) ##STR00304##

(564) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.37-7.35 (2H, m), 7.23-7.21 (1H, m), 7.14 (1H, d, J=5.2 Hz), 6.81 (1H, d, J=5.2 Hz), 5.24 (2H, s), 3.65 (3H, s), 2.53 (3H, s), 2.25 (3H, s), 2.12 (3H, s).

Production Example 259

(565) A mixture of 0.56 g of C11A, 0.25 g of C259A, 0.36 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.49 g of 1-[2-(1-furan-2-yl-ethylideneaminooxymethyl) 3-methylphenyl]-4-meth yl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 259).

(566) ##STR00305##

(567) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.44 (1H, t, J=0.8 Hz), 7.44-7.37 (2H, m), 7.24-7.23 (1H, m), 6.60 (1H, d, J=3.2 Hz), 6.42-6.41 (1H, m), 5.23 (2H, s), 3.66 (3H, s), 2.53 (3H, s), 2.05 (3H, s).

Production Example 260

(568) A mixture of 0.28 g of C11A, 0.19 g of C260A, 0.26 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.23 g of 1-{2-[1-(6-fluorobenzo[d]isoxazol-3-yl)ethylideneaminooxymethyl]-3-methylphenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 260).

(569) ##STR00306##

(570) .sup.1H-NMR (CHCl.sub.3) δ(ppm): 7.90 (1H, dd, J=8.8, 5.4 Hz), 7.44-7.39 (2H, m), 7.29-7.26 (1H, m), 7.22 (1H, dd, J=8.4, 2.1 Hz), 7.09 (1H, td, J=8.9, 2.1 Hz), 5.40 (2H, s), 3.67 (3H, s), 2.57 (3H, s), 2.30 (3H, s).

Production Example 261

(571) A mixture of 0.30 g of C14A, 0.19 g of C260A, 0.26 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.44 g of 1-{3-ethyl-2-[1-(6-fluorobenzo[d]isoxazol-3-yl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 261).

(572) ##STR00307##

(573) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.91 (1H, dd, J=8.7, 5.5 Hz), 7.49-7.44 (2H, m), 7.28-7.26 (1H, m), 7.23 (1H, dd, J=8.4, 2.2 Hz), 7.09 (1H, td, J=8.9, 2.1 Hz), 5.43 (2H, s), 3.63 (3H, s), 2.92 (2H, q, J=7.6 Hz), 2.28 (3H, s), 1.31 (3H, t, J=7.6 Hz).

Production Example 262

(574) A mixture of 0.31 g of C17A, 0.19 g of C260A, 0.26 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.33 g of 1-{3-cyclopropyl-2-[1-(6-fluorobenzo[d]isoxazol-3-yl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 262).

(575) ##STR00308##

(576) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.90 (1H, dd, J=8.8, 5.4 Hz), 7.42 (1H, t, J=7.9 Hz), 7.26-7.21 (3H, m), 7.08 (1H, td, J=8.9, 2.1 Hz), 5.62 (2H, s), 3.64 (3H, s), 2.28 (3H, s), 2.26-2.21 (1H, m), 1.09-1.05 (2H, m), 0.82-0.78 (2H, m).

Production Example 263

(577) A mixture of 0.30 g of C2A, 0.19 g of C260A, 0.26 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.16 g of 1-{3-chloro-2-[1-(6-fluorobenzo[d]isoxazol-3-yl)ethylideneaminooxy methyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 263).

(578) ##STR00309##

(579) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.95 (1H, dd, J=8.8, 5.2 Hz), 7.63 (1H, d, J=8.2 Hz), 7.46 (1H, t, J=8.0 Hz), 7.37 (1H, d, J=7.9 Hz), 7.25-7.21 (1H, m), 7.12-7.06 (1H, m), 5.62 (2H, s), 3.65 (3H, s), 2.25 (3H, s).

Production Example 264

(580) A mixture of 0.42 g of C11A, 0.23 g of C261A, 0.26 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.33 g of 1-{2-[1-(1,5-dimethyl-1H-pyrazol-3-yl)ethylideneaminooxymethyl]-3-methylphenyl}-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 264).

(581) ##STR00310##

(582) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.36 (2H, d, J=5.2 Hz), 7.21 (1H, t, J=4.6 Hz), 6.27 (1H, s), 5.19 (2H, s), 3.75 (3H, s), 3.68 (3H, s), 2.53 (3H, s), 2.25 (3H, s), 2.10 (3H, s).

Production Example 265

(583) A mixture of 0.42 g of C11A, 0.25 g of C262A, 0.27 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.35 g of 1-[2-(5-mercapto-1,4-dimethylpenta-2,4-dienylideneaminooxymethyl)-3-methylphenyl]-4-methyl-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 265).

(584) ##STR00311##

(585) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.39-7.37 (2H, m), 7.31-7.29 (1H, m), 7.25-7.21 (3H, m), 6.82 (1H, d, J=16.4 Hz), 6.57 (1H, d, J=16.4 Hz), 5.18 (2H, s), 3.70 (3H, s), 2.52 (3H, s), 1.92 (3H, s).

Production Example 266

(586) A mixture of 0.28 g of C11A, 0.18 g of C263A, 0.26 g of potassium carbonate, and 10 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 0.18 g of 1-methyl-4-{3-methyl-2-[1-(2-thiophenyl-3-ylcyclopropyl)ethylideneaminooxymethyl}phenyl)-1,4-dihydrotetrazol-5-one (hereinafter referred to as the present compound 266).

(587) ##STR00312##

(588) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.36-7.34 (2H, m), 7.25-7.19 (2H, m), 6.91-6.90 (1H, m), 6.83-6.81 (1H, m), 5.06 (2H, s), 3 the production of intermediates of the above present compounds. 66 (3H, s), 2.50 (3H, s), 2.18-2.13 (1H, m), 1.72-1.67 (1H, m), 1.64 (3H, s), 1.35-1.28 (1H, m), 1.08-1.03 (1H, m).

(589) Regarding the production of the compound (2), Synthesis Example will be shown below.

Synthesis Example 1

(590) A mixture of 7.88 g of C101A, 9.20 g of C151A, 11.06 g of potassium carbonate, and 100 mL of acetonitrile was stirred while heating under reflux for 7 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. The obtained residue was subjected to silica gel column chromatography to obtain 9.51 g of 1-indan-4-ylethanone O-(2-methyl-6-nitrobenzyl)oxime.

(591) ##STR00313##

(592) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.57 (1H, d, J=7.9 Hz), 7.41 (1H, d, J=7.6 Hz), 7.33 (1H, t, J=7.9 Hz), 7.21-7.17 (1H, m), 7.15-7.11 (2H, m), 5.45 (2H, s), 2.88 (2H, t, J=7.5 Hz), 2.82 (2H, t, J=7.5 Hz), 2.53 (3H, s), 2.15 (3H, s), 1.96 (2H, sext, J=7.4 Hz).

(593) Regarding the production of intermediates for producing the above present compounds, Reference Production Examples will be shown below.

Reference Production Example 1

Step (1)

(594) Anhydrous aluminum trichloride (21.9 g) was added to 250 mL of N,N-dimethylformamide under ice cooling, followed by stirring for 15 minutes. To this was added 10.7 g of sodium azide and the mixture was stirred for 15 minutes, followed by the addition of 22.5 g of 1-fluoro-3-isocyanate-2-methylbenzene and further stirring at 80° C. for 3.5 hours. After cooling, the reaction solution was added in a mixture of 34 g of sodium nitrite, 2 L of water, and 500 g of ice while stirring. The mixture was acidified with 10% hydrochloric acid and then extracted with ethyl acetate. The organic layer was washed in turn with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain 27.5 g of 1-(2-methyl-3-fluorophenyl)-1,4-dihydrotetrazol-5-one.

(595) ##STR00314##

(596) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 12.93 (1H, s), 7.07-7.36 (3H, m), 2.21 (3H, s).

Step (2)

(597) To a mixture of 10.00 g of 1-(2-methyl-3-fluorophenyl)-1,4-dihydrotetrazol-5-one and 100 mL of N,N-dimethylformamide, 2.47 g of 55% sodium hydride was added under ice cooling. The temperature of the mixture was raised to room temperature, followed by stirring for one hour. To the reaction mixture, 3.5 mL of methyl iodide was added under ice cooling. The temperature of the mixture was raised to room temperature, followed by stirring for 14 hours. Water was poured into the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed in turn with 10% hydrochloric acid, water, and a saturated saline solution, dried over anhydrous magnesiumsulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 2.19 g of 1-(2-methyl-3-fluorophenyl)-4-methyl-1,4-dihydrotetrazol-5-one.

(598) ##STR00315##

(599) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.29 (1H, dt, J=5.9, 8.3 Hz), 7.16-7.20 (2H, m), 3.70 (3H, s), 2.19 (3H, s).

Step (3)

(600) A mixture of 2.19 g of 1-(2-methyl-3-fluorophenyl)-4-methyl-1,4-dihydrotetrazol-5-one, 0.52 g of 1,1′-azobis(cyclohexane-1-carbonitrile), 2.16 g of N-bromosuccinimide, and 40 mL of chlorobenzene was stirred while heating under reflux for 5 hours. After cooling, water was poured into the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed in turn with water and a saturated saline solution, dried over anhydrous magnesiumsulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 2.36 g of 1-(2-bromomethyl-3-fluorophenyl)-4-methyl-1,4-dihydrotetrazol-5-on e (C1A).

(601) ##STR00316##

(602) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.47 (1H, dt, J=5.9, 8.0 Hz), 7.23-7.30 (2H, m), 4.64 (2H, s), 3.75 (3H, s).

Reference Production Example 2

Step (1)

(603) Anhydrous aluminum trichloride (21.9 g) was added to 250 mL of N,N-dimethylformamide under ice cooling, followed by stirring for 15 minutes. To this was added 10.7 g of sodium azide and the mixture was stirred for 15 minutes, followed by the addition of 25.0 g of 1-chloro-3-isocyanate-2-methylbenzene and further heating at 80° C. for 5 hours. After cooling, the reaction solution was added in a mixture of 35 g of sodium nitrite, 2 L of water, and 500 g of ice while stirring.

(604) The mixture was acidified with 10% hydrochloric acid and then extracted with ethyl acetate. The organic layer was washed in turn with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain 17.0 g of 1-(2-methyl-3-chlorophenyl)-1,4-dihydrotetrazol-5-one.

(605) ##STR00317##

(606) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 13.08 (1H, s), 7.57 (1H, dd, J=6.8, 2.2 Hz), 7.28-7.36 (2H, m), 2.32 (3H, s).

Step (2)

(607) To a mixture of 10.00 g of 1-(2-methyl-3-chlorophenyl)-1,4-dihydrotetrazol-5-one and 100 mL of N,N-dimethylformamide, 2.30 g of 55% sodium hydride was added under ice cooling. The temperature of the mixture was raised to room temperature, followed by stirring for one hour. To the reaction mixture, 3.2 mL of methyl iodide was added under ice cooling. The temperature of the mixture was raised to room temperature, followed by stirring for 14 hours. Water was poured into the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed in turn with 10% hydrochloric acid, water, and a saturated saline solution, dried over anhydrous magnesiumsulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 1.56 g of 1-(2-methyl-3-chlorophenyl)-4-methyl-1,4-dihydrotetrazol-5-one.

(608) ##STR00318##

(609) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.52 (1H, dd, J=2.7, 6.8 Hz), 7.28 (1H, d, J=7.1 Hz), 7.27 (1H, d, J=2.7 Hz), 3.73 (3H, s), 2.30 (3H, s).

Step (3)

(610) A mixture of 1.56 g of 1-(2-methyl-3-chlorophenyl)-4-methyl-1,4-dihydrotetrazol-5-one, 0.34 g of 1,1′-azobis(cyclohexane-1-carbonitrile), 1.42 g of N-bromosuccinimide, and 30 mL of chlorobenzene was stirred while heating under reflux for 5 hours. After cooling, water was poured into the reaction mixture, followed by extraction ethyl acetate. The organic layer was washed in turn with water and a saturated saline solution, dried over anhydrous magnesiumsulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 1.94 g of 1-(2-bromomethyl-3-chlorophenyl)-4-methyl-1,4-dihydrotetrazol-5-one (C2A).

(611) ##STR00319##

(612) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.58 (1H, dd, J=1.2, 8.1 Hz), 7.43 (1H, t, J=8.1 Hz), 7.35 (1H, dd, J=1.2, 8.1 Hz), 4.69 (2H, s), 3.76 (3H, s).

Reference Production Example 3

(613) A mixture of 21.5 g of 3-chloro-2-methylbenzoic acid, 17.6 g of oxalyl dichloride, about 50 mg of N,N-dimethylformamide and 300 mL of tetrahydrofuran was stirred at 25° C. for one hour. The reaction mixture was concentrated under reduced pressure to obtain 3-chloro-2-methylbenzoic acid chloride.

(614) A mixture of 33.6 g of aluminum chloride, 49.2 g of sodium azide, and 100 mL of tetrahydrofuran was stirred while heating under reflux for 2 hours. After ice cooling of the reaction mixture, a mixture of 3-chloro-2-methylbenzoic acid chloride and 100 mL of tetrahydrofuran was added, followed by stirring while heating under reflux for 10 hours. After cooling, the reaction mixture was added in a mixture of 75.6 g of sodium nitrite and 500 mL of water while stirring. The mixture was acidified with concentrated hydrochloric acid and then extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 1-(2-methyl-3-chlorophenyl)-1,4-dihydrotetrazol-5-one.

(615) The obtained mixture of 1-(2-methyl-3-chlorophenyl)-1,4-dihydrotetrazol-5-one, 57.5 g of potassium carbonate, 19.1 g of dimethylsulfuric acid, and 150 mL of N,N-dimethylformamide was stirred at 25° C. for one hour. An aqueous saturated sodium bicarbonate solution was poured into the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with an aqueous saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain 21.6 g of 1-(2-methyl-3-chlorophenyl)-4-methyl-1,4-dihydrotetrazol-5-one (C3A).

Reference Production Example 4

(616) Under ice cooling, to a mixture of 30 mL of methyl chloroformate and 50 mL of tetrahydrofuran, 5.00 g of 3-amino-1-chloro-2-methylbenzene was added dropwise and the mixture was stirred at 25° C. for 0.5 hour. Water was poured into the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with an aqueous saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain 5.80 g of 1-chloro-2-methyl-3-methoxycarbonylaminobenzene.

(617) A mixture of 5.80 g of 1-chloro-2-methyl-3-methoxycarbonylaminobenzene, 7.53 g of phosphorus pentachloride, and 50 mL of chlorobenzene was stirred while heating under reflux for one hour. The reaction mixture was concentrated under reduced pressure to obtain 1-chloro-3-isocyanate-2-methylbenzene.

(618) A mixture of 4.71 g of aluminum chloride, 6.89 g of sodium azide, and 100 mL of tetrahydrofuran was stirred while heating under reflux for one hour. After ice cooling of the reaction mixture, a mixture of 1-chloro-3-isocyanate-2-methylbenzene obtained above and 10 mL of tetrahydrofuran was added, followed by stirring while heating under reflux for 5 hours. After cooling, the reaction mixture was added in a mixture of 10.59 g of sodium nitrite and 300 mL of water while stirring. The mixture was acidified with concentrated hydrochloric acid and then extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 1-(2-methyl-3-chlorophenyl)-1,4-dihydrotetrazol-5-one.

(619) A mixture of the obtained 1-(2-methyl-3-chlorophenyl)-1,4-dihydrotetrazol-5-one, 16.11 g of potassium carbonate, 5.34 g of dimethylsulfuric acid, and 150 mL of N,N-dimethylformamide was stirred at 25° C. for one hour. An aqueous saturated sodium bicarbonate solution was poured into the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with an aqueous saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain 4.80 g of 1-(2-methyl-3-chlorophenyl)-4-methyl-1,4-dihydrotetrazol-5-one (C4A).

Reference Production Example 5

Step (1)

(620) A mixture of 25.0 g of 1-bromo-2-methyl-3-aminobenzene, 60.0 g of triphosgene, and 400 mL of toluene was stirred while heating under reflux for 3 hours. The cooled reaction mixture was concentrated under reduced pressure to obtain 30.3 g of 1-bromo-3-isocyanate-2-methylbenzene.

(621) ##STR00320##

(622) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.39 (1H, dd, J=1.5, 7.7 Hz), 7.05 (1H, dd, J=1.7, 8.0 Hz), 7.00 (1H, dt, J=0.5, 8.0 Hz), 2.42 (3H, s).

Step (2)

(623) Anhydrous aluminum trichloride (19.7 g) was added to 220 mL of N,N-dimethylformamide under ice cooling, followed by stirring for 15 minutes. To this was added 9.6 g of sodium azide and, after stirring for 15 minutes, 30.3 g of 1-bromo-3-isocyanate-2-methylbenzene was added, followed by heating at 80° C. for 5 hours. After cooling, the reaction solution was added in a mixture of 33 g of sodium nitrite, 2 L of water, and 500 g of ice while stirring. The mixture was acidified with 10% hydrochloric acid and then extracted with ethyl acetate. The organic layer was washed in turn with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain 31.4 g of 1-(2-methyl-3-bromophenyl)-1,4-dihydrotetrazol-5-one.

(624) ##STR00321##

(625) .sup.1H-NMR (DMSO-d.sub.6) δ(ppm): 14.72 (1H, s), 7.82 (1H, dd, J=8.0, 1.0 Hz), 7.49 (1H, dd, J=8.2, 1.1 Hz), 7.34 (1H, t, J=7.2 Hz), 2.22 (3H, s).

Step (3)

(626) To a mixture of 31.4 g of 1-(2-methyl-3-bromophenyl)-1,4-dihydrotetrazol-5-one and 250 mL of N,N-dimethylformamide, 5.90 g of 60% sodium hydride was added under ice cooling. The temperature of the mixture was raised to room temperature, followed by stirring for one hour. Under ice cooling, 8.4 mL of methyl iodide was added to the reaction mixture. The temperature of the mixture was raised to room temperature, followed by stirring for 14 hours. Water was poured into the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed in turn with 10% hydrochloric acid, water, and a saturated saline solution, dried over anhydrous magnesiumsulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 8.47 g of C6A.

(627) ##STR00322##

(628) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.71 (1H, dd, J=1.2, 8.3 Hz), 7.30 (1H, dd, J=1.0, 8.0 Hz), 7.21 (1H, dt, J=0.5, 7.8 Hz), 3.73 (3H, s), 2.33 (3H, s).

Step (4)

(629) A mixture of 8.47 g of 1-(2-methyl-3-bromophenyl)-4-methyl-1,4-dihydrotetrazol-5-one, 1.54 g of 1,1′-azobis(cyclohexane-1-carbonitrile), 6.44 g of N-bromosuccinimide, and 125 mL of chlorobenzene was stirred while heating under reflux for 5 hours. After cooling, water was poured into the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed in turn with water and a saturated saline solution, dried over anhydrous magnesiumsulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 7.52 g of 1-(2-bromomethyl-3-bromophenyl)-4-methyl-1,4-dihydrotetrazol-5-one (C5A).

(630) ##STR00323##

(631) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 3.76 (3H, s), 4.71 (2H, s), 7.34 (1H, t, J=7.8 Hz), 7.38 (1H, dd, J=8.0, 1.7 Hz), 7.77 (1H, dd, J=7.8, 1.7 Hz).

Reference Production Example 6

(632) A mixture of 146.0 g of 3-bromo-2-methylbenzoic acid, 94.8 g of oxalyl dichloride, about 15 mg of N,N-dimethylformamide, and 500 mL of tetrahydrofuran was stirred at 25° C. for one hour. The reaction mixture was concentrated under reduced pressure to obtain 3-bromo-2-methylbenzoic acid chloride.

(633) A mixture of 181.0 g of aluminum chloride, 265.0 g of sodium azide, and 300 mL of tetrahydrofuran was stirred while heating under reflux for 2 hours. After ice cooling of the reaction mixture, a mixture of 3-bromo-2-methylbenzoic acid chloride obtained above and 200 mL of tetrahydrofuran was added, followed by stirring while heating under reflux for 10 hours. After cooling, the reaction mixture was added in a mixture of 407 g of sodium nitrite and 1,500 mL of water while stirring. The mixture was acidified with concentrated hydrochloric acid and then extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 1-(2-methyl-3-bromophenyl)-1,4-dihydrotetrazol-5-one.

(634) A mixture of 1-(2-methyl-3-bromophenyl)-1,4-dihydrotetrazol-5-one obtained above, 310.0 g of potassium carbonate, 103.0 g of dimethylsulfuric acid, and 500 mL of N,N-dimethylformamide was stirred at 25° C. for one hour. An aqueous saturated sodium bicarbonate solution was poured into the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with an aqueous saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain 142.0 g of 1-(2-methyl-3-bromophenyl)-4-methyl-1,4-dihydrotetrazol-5-one (C6A).

Reference Production Example 7

Step (1)

(635) A mixture of 10.00 g of 3-iodo-2-methylbenzoic acid, 5.33 g of oxalyl dichloride, five drops of N,N-dimethylformamide, and 200 mL of tetrahydrofuran was stirred at 25° C. for one hour. The reaction mixture was concentrated under reduced pressure to obtain 3-iodo-2-methylbenzoic acid chloride.

(636) A mixture of 10.20 g of aluminum trichloride, 14.90 g of sodium azide, and 100 mL of tetrahydrofuran was stirred while heating under reflux for 2 hours. After ice cooling of the reaction mixture, a mixture of 3-iodo-2-methylbenzoic acid chloride obtained above and 100 mL of tetrahydrofuran was added, followed by stirring while heating under reflux for 10 hours. After cooling, the reaction mixture was added in a mixture of 22.90 g of sodium nitrite and 200 mL of water while stirring. The mixture was acidified with concentrated hydrochloric acid and then extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 1-(2-methyl-3-iodophenyl)-1,4-dihydrotetrazol-5-one.

(637) A mixture of 1-(2-methyl-3-iodophenyl)-1,4-dihydrotetrazol-5-one obtained above, 17.40 g of potassium carbonate, 5.78 g of dimethylsulfuric acid, and 150 mL of N,N-dimethylformamide was stirred at 25° C. for one hour. An aqueous saturated sodium bicarbonate solution was poured into the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with an aqueous saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain 8.10 g of 1-(2-methyl-3-iodophenyl)-4-methyl-1,4-dihydrotetrazol-5-one.

(638) ##STR00324##

(639) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 2.37 (3H, s), 3.72 (3H, s), 7.04 (1H, t, J=8.0 Hz), 7.32 (1H, d, J=7.7 Hz), 7.99 (1H, d, 8.0 Hz).

Step (2)

(640) A mixture of 8.10 g of 1-(2-methyl-3-iodophenyl)-4-methyl-1,4-dihydrotetrazol-5-one, 1.25 g of 1,1′-azobis(cyclohexane-1-carbonitrile), 5.24 g of N-bromosuccinimide, and 100 mL of chlorobenzene was stirred while heating under reflux for 5 hours. After cooling, water was poured into the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed in turn with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 3.11 g of 1-(2-bromomethyl-3-iodophenyl)-4-methyl-1,4-dihydrotetrazol-5-one (C7A).

(641) ##STR00325##

(642) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 3.75 (3H, s), 4.71 (2H, s), 7.17 (1H, t, J=8.0 Hz), 7.39 (1H, d, J=8.0 Hz), 8.04 (1H, J=8.0 Hz).

Reference Production Example 8

Step (1)

(643) A mixture of 15.0 g of 3-amino-1-methoxy-2-methylbenzene, 48.7 g of triphosgene, and 350 mL of toluene was stirred while heating under reflux for 3 hours. The cooled reaction mixture was concentrated under reduced pressure to obtain 17.0 g of 1-methoxy-3-isocyanate-2-methylbenzene.

(644) ##STR00326##

(645) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 2.19 (3H, s), 3.82 (3H, s), 6.69 (1H, d, J=8.2 Hz), 6.72 (1H, dd, J=0.5, 8.0 Hz), 7.09 (1H, t, J=8.2 Hz).

Step (2)

(646) Under ice cooling, 16.0 g of anhydrous aluminum trichloride was added to 180 mL of N,N-dimethylformamide, followed by stirring for 15 minutes. To this was added 7.8 g of sodium azide and, after stirring for 15 minutes, 17.0 g of 1-methoxy-3-isocyanate-2-methylbenzene was added and the mixture was heated at 80° C. for 4.5 hours. After cooling, the reaction solution was added in a mixture of 25 g of sodium nitrite, 2 L of water, and 500 g of ice while stirring. The mixture was acidified with 10% hydrochloric acid and then extracted with ethyl acetate. The organic layer was washed in turn with water and a saturated saline solution, dried over anhydrous magnesiumsulfate, and then concentrated under reduced pressure to obtain 16.2 g of 1-(2-methyl-3-methoxyphenyl)-1,4-dihydrotetrazol-5-one.

(647) ##STR00327##

(648) .sup.1H-NMR (DMSO-d.sub.6) δ(ppm): 1.99 (3H, s), 3.87 (3H, s), 7.01 (1H, d, J=8.1 Hz), 7.17 (1H, d, J=8.1 Hz). 7.36 (1H, t, J=8.3 Hz), 14.63 (1H, s).

Step (3)

(649) To a mixture of 10.00 g of 1-(2-methyl-3-methoxyphenyl)-1,4-dihydrotetrazol-5-one and 100 mL of N,N-dimethylformamide, 2.47 g of 55% sodium hydride was added under ice cooling. The temperature of the mixture was raised to room temperature, followed by stirring for one hour. To the reaction mixture, 3.5 mL of methyl iodide was added under ice cooling. The temperature of the mixture was raised to room temperature, followed by stirring for 14 hours. Water was poured into the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed in turn with 10% hydrochloric acid, water, and a saturated saline solution, dried over anhydrous magnesiumsulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 2.19 g of 1-(2-methyl-3-methoxyphenyl)-4-methyl-1,4-dihydrotetrazol-5-one.

(650) ##STR00328##

(651) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 2.11 (3H, s), 3, 72 (3H, s), 3.88 (3H, s), 6.95 (1H, d, J=8.2 Hz), 6.98 (1H, d, J=8.5 Hz), 7.29 (1H, t, J=8.2 Hz)

Step (4)

(652) A mixture of 2.19 g of 1-(2-methyl-3-methoxyphenyl)-4-methyl-1,4-dihydrotetrazol-5-one, 0.52 g of 1,1′-azobis(cyclohexane-1-carbonitrile), 2.16 g of N-bromosuccinimide, and 40 mL of chlorobenzene was stirred while heating under reflux for 5 hours. After cooling, water was poured into the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed in turn with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 2.36 g of 1-(2-bromomethyl-3-methoxyphenyl)-4-methyl-1,4-dihydrotetrazol-5-one (C8A).

(653) ##STR00329##

(654) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 3.74 (3H, s), 3.96 (3H, s), 4.93 (2H, s), 7.02 (1H, dd, J=1.0, 8.5 Hz), 7.04 (1H, d, J=9.0 Hz), 7.43 (1H, t, J=8.1 Hz).

Reference Production Example 9

Step (1)

(655) A mixture of 5.00 g of 3-trifluoromethyl-2-methylbenzoic acid, 3.42 g of oxalyl dichloride, about 50 mg of N,N-dimethylformamide, and 200 mL of tetrahydrofuran was stirred at 25° C. for one hour. The reaction mixture was concentrated under reduced pressure to obtain 3-trifluoromethyl-2-methylbenzoic acid chloride.

(656) A mixture of 6.53 g of aluminum trichloride, 9.55 g of sodium azide, and 100 mL of tetrahydrofuran was stirred while heating under reflux for 2 hours. After ice cooling of the reaction mixture, a mixture of 3-trifluoromethyl-2-methylbenzoic acid chloride obtained above and 100 mL of tetrahydrofuran was added, followed by stirring while heating under reflux for 10 hours. After cooling, the reaction mixture was added in a mixture of 14.7 g of sodium nitrite and 200 mL of water while stirring. The mixture was acidified with concentrated hydrochloric acid and then extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain a crude product of 1-(2-methyl-3-trifluoromethylphenyl)-1,4-dihydrotetrazol-5-one. A mixture of the crude product of 1-(2-methyl-3-trifluoromethylphenyl)-1,4-dihydrotetrazol-5-one obtained above, 11.20 g of potassium carbonate, 3.71 g of dimethylsulfuric acid, and 150 mL of N,N-dimethylformamide was stirred at 25° C. for one hour. An aqueous saturated sodium bicarbonate solution was poured into the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with an aqueous saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain 5.13 g of 1-(2-methyl-3-trifluoromethylphenyl)-4-methyl-1,4-dihydrotetrazol-5-one.

(657) ##STR00330##

(658) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 2.42 (3H, s), 3.75 (3H, s), 7.52 (1H, t, J=8.2 Hz), 7.62 (1H, dd, J=1.2, 7.7 Hz), 8.02 (1H, dd, J=1.2, 8.2 Hz).

Step (2)

(659) A mixture of 1.00 g of 1-(2-methyl-3-trifluoromethylphenyl)-4-methyl-1,4-dihydrotetrazol-5-one, 0.38 g of 1,1′-azobis(cyclohexane-1-carbonitrile), 0.79 g of N-bromosuccinimide, and 30 mL of chlorobenzene was stirred while heating under reflux for 5 hours. After cooling, water was poured into the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed in turn with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 1.21 g of 1-(2-bromomethyl-3-trifluoromethylphenyl)-4-methyl-1,4-dihydrotetrazol-5-one (C9A).

(660) ##STR00331##

(661) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 3.77 (3H, s), 4.75 (2H, s), 7.62 (1H, d, J=5.5 Hz), 7.63 (1H, d, J=3.4 Hz), 7.85 (1H, dd, J=3.6, 5.8 Hz).

Reference Production Example 10

Step (1)

(662) A mixture of 5.0 g of 3-nitro-2-methylbenzoic acid, 3.9 g of oxalyl dichloride, about 50 mg of N,N-dimethylformamide, and 200 mL of tetrahydrofuran was stirred at 25° C. for one hour. The reaction mixture was concentrated under reduced pressure to obtain 3-nitro-2-methylbenzoic acid chloride.

(663) A mixture of 7.4 g of aluminumtrichloride, 11.0 g of sodiumazide, and 100 mL of tetrahydrofuran was stirred while heating under reflux for 2 hours. After ice cooling of the reaction mixture, a mixture of 3-nitro-2-methylbenzoic acid chloride obtained above and 100 mL of tetrahydrofuran was added, followed by stirring while heating under reflux for 10 hours. After cooling, the reaction mixture was added in a mixture of 16.6 g of sodium nitrite and 200 mL of water while stirring.

(664) The mixture was acidified with concentrated hydrochloric acid and then extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 1-(2-methyl-3-nitrophenyl)-1,4-dihydrotetrazol-5-one.

(665) A mixture of 1-(2-methyl-3-nitrophenyl)-1,4-dihydrotetrazol-5-one thus obtained, 12.6 g of potassium carbonate, 13.8 g of dimethylsulfuric acid, and 150 mL of N,N-dimethylformamide was stirred at 25° C. for one hour. An aqueous saturated sodium bicarbonate solution was poured into the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with an aqueous saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain 5.3 g of 1-(2-methyl-3-nitrophenyl)-4-methyl-1,4-dihydrotetrazol-5-one.

(666) ##STR00332##

(667) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 2.42 (3H, s), 3.75 (3H, s), 7.52 (1H, t, J=8.2 Hz), 7.62 (1H, dd, J=1.2, 7.7 Hz), 8.02 (1H, d, J=1.2, 8.2 Hz).

Step (2)

(668) A mixture of 1.00 g of 1-(2-methyl-3-nitrophenyl)-4-methyl-1,4-dihydrotetrazol-5-one, 0.42 g of 1,1′-azobis(cyclohexane-1-carbonitrile), 0.87 g of N-bromosuccinimide, and 30 mL of chlorobenzene was stirred while heating under reflux for 5 hours. After allowing to cool, water was poured into the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed in turn with water and an aqueous saturated sodium bicarbonate solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 1.00 g of 1-(2-bromomethyl-3-nitrophenyl)-4-methyl-1,4-dihydrotetrazol-5-one (C10A).

(669) ##STR00333##

(670) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 3.72 (3H, s), 5.63 (2H, s), 7.61 (1H, t, J=8.0 Hz), 7.70 (1H, d, J=8.1 Hz), 7.97 (1H, d, J=8.1 Hz).

Reference Production Example 11

Step (1)

(671) A mixture of 45.0 g C5A, 37.4 g of sodium methoxide, and 600 mL of tetrahydrofuran was stirred at 25° C. for 3 hours. An aqueous saturated sodium bicarbonate solution was poured into the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with an aqueous saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain 1-(2-methoxymethyl-3-bromophenyl)-4-methyl-1,4-dihydrotetrazol-5-one.

(672) ##STR00334##

(673) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 3.23 (3H, s), 3.72 (3H, s), 4.67 (2H, s), 7.33 (1H, t, J=7.8 Hz), 7.38 (1H, dd, J=1.2, 8.1 Hz), 7.76 (1H, dd, J=1.5, 7.8 Hz).

Step (2)

(674) A mixture of 1-(2-methoxymethyl-3-bromophenyl)-4-methyl-1,4-dihydrotetrazol-5-one obtained above, 23.2 g of methylboronic acid, 66.7 g of cesium fluoride, 10.6 g of [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct, and 500 mL of dioxane was stirred at 90° C. for 5.5 hours. After cooling, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 1-(2-methoxymethyl-3-methylphenyl)-4-methyl-1,4-dihydrotetrazol-5-one.

(675) ##STR00335##

(676) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 2.48 (3H, s), 3.23 (3H, s), 3.72 (3H, s), 4.42 (2H, s), 7.21 (1H, t, J=5.1 Hz), 7.35 (2H, d, J=4.8 Hz).

Step (3)

(677) A mixture of 1-(2-methoxymethyl-3-methylphenyl)-4-methyl-1,4-dihydrotetrazol-5-one obtained above, 50 mL of acetic acid, and 50 mL of a 25% hydrogen bromide-acetic acid solution was stirred at 65° C. for one hour. An aqueous saturated sodium chloride solution was poured into the reaction mixture, followed by extraction with ethyl acetate. The organic layer was in turn washed with an aqueous saturated sodium bicarbonate solution and anhydrous sodium sulfate, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain 27.9 g of 1-(2-bromomethyl-3-methylphenyl)-4-methyl-1,4-dihydrotetrazol-5-one (C11A).

(678) ##STR00336##

(679) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 2.51 (3H, s), 3.75 (3H, s), 4.51 (2H, s), 7.22-7.24 (1H, m), 7.36-7.39 (2H, m).

Reference Production Example 12

Step (1)

(680) To a mixture of 15.1 g of 2-amino-6-methylbenzoic acid, 150 mL of ethyl acetate, and 150 mL of ethanol, a 2.0M diethyl ether solution of trimethylsilyldiazomethane was added under ice cooling. After stirring at room temperature for 4 hours, the mixture was concentrated under reduced pressure to obtain 16.5 of 2-amino-6-methylbenzoic acid methyl ester.

(681) ##STR00337##

(682) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 6.94 (1H, t, J=8.0 Hz), 6.40-6.38 (2H, m), 4.96 (2H, s), 3.75 (3H, s), 2.29 (3H, s).

Step (2)

(683) To a mixture of 16.5 g of 2-amino-6-methylbenzoic acid methyl ester and 300 mL of toluene, 44.5 g of triphosgene was added at room temperature, followed by stirring while heating under reflux for 2.5 hours. After concentration under reduced pressure, 2-isocyanate-6-methylbenzoic acid methyl ester was obtained.

(684) ##STR00338##

(685) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.28-7.24 (1H, m), 7.07-7.04 (1H, m), 6.98-6.95 (1H, m), 3.97 (3H, s), 2.36 (3H, s).

Step (3)

(686) Under ice cooling, 16.0 g of aluminum trichloride was added to 200 mL of N,N-dimethylformamide, followed by stirring for 0.5 hour. Sodium azide (7.2 g) was added and, after stirring for 0.5 hour, 2-isocyanate-6-methylbenzoic acid methyl ester obtained above was added, followed by heating and stirring at 80° C. for 8 hours. After cooling, 11.5 g of sodium nitrite and 300 mL of ice water were added to the reaction solution, and the mixture was acidified with 10% hydrochloric acid and then extracted with ethyl acetate. The organic layer was washed in turn with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain 2-methyl-6-(5-oxo-4,5-dihydrotetrazol-1-yl)benzoic acid methyl ester.

(687) To a mixture of 2-methyl-6-(5-oxo-4,5-dihydrotetrazol-1-yl)benzoic acid methyl ester thus obtained and 300 mL of N,N-dimethylformamide, 42.0 g of potassium carbonate and 18.9 g of dimethylsulfuric acid were added at room temperature, followed by stirring for 24 hours. Water was poured into the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed in turn with water and an aqueous saturated sodium bicarbonate solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 13.9 g of 2-methyl-6-(4-methyl-5-oxo-4,5-dihydrotetrazol-1-yl)benzoic acid methyl ester.

(688) ##STR00339##

(689) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.50-7.46 (2H, m), 7.35-7.33 (1H, m), 3.83 (3H, s), 3.69 (3H, s), 2.48 (3H, s).

Step (4)

(690) To a mixture of 25 g of 2-methyl-6-(4-methyl-5-oxo-4,5-dihydro-tetrazol-1-yl)benzoic acid methyl ester and 300 mL of tetrahydrofuran, 201 mL of a 1.0M-tetrahydrofuran solution of lithiumtriethylborane hydride was added at 0° C., followed by stirring at room temperature for 0.5 hour.

(691) Water was poured into the reaction solution, and the solution was acidified with 10% hydrochloric acid and extracted with ethyl acetate.

(692) The organic layer was washed with water, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain 21.2 g of 1-(2-hydroxymethyl-3-methylphenyl)-4-methyl-1,4-dihydrotetrazol-5-one.

(693) ##STR00340##

(694) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.39-7.34 (2H, m), 7.21 (1H, dd, J=6.5, 2.8 Hz), 4.48 (2H, s), 3.75 (3H, s), 2.57 (3H, s), 1.59 (1H, br s).

Step (5)

(695) To a mixture of 21.2 g of 1-(2-hydroxymethyl-3-methylphenyl)-4-methyl-1,4-dihydrotetrazol-5-one and 300 mL of chloroform, 52.1 g of phosphorus tribromide was added, followed by stirring at room temperature for one hour. Ice water (200 mL) was poured into the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain 26.0 g of C11A.

Reference Production Example 13

Step (1)

(696) A mixture of 33.5 g of 2-methyl-3-nitrophenol, 41 g of iodoethane, 90 g of potassium carbonate, and 400 mL of acetone was stirred while heating under reflux for 10 hours. The mixture was cooled to room temperature and filtered, and the filtrate was concentrated. After extraction with ethyl acetate, the organic layer was washed in turn with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 39.9 g of 1-ethoxy-2-methyl-3-nitrobenzene.

(697) ##STR00341##

(698) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.39 (1H, dd, J=8.2, 1.0 Hz), 7.24 (1H, t, J=8.3 Hz), 7.02 (1H, d, J=8.2 Hz), 4.08 (2H, q, J=7.0 Hz), 2.37 (3H, s), 1.50-1.42 (3H, m).

Step (2)

(699) A mixture of 39.9 g of 1-ethoxy-2-methyl-3-nitrobenzene, 4 g of palladium-carbon (palladium: 5%), and 200 mL of ethanol was stirred under hydrogen atmosphere at room temperature for 18 hours. The mixture was filtered and the filtrate was concentrated to obtain 33.0 g of 3-ethoxy-2-methylaniline.

(700) ##STR00342##

(701) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 6.95 (1H, t, J=8.1 Hz), 6.35 (1H, d, J=2.9 Hz), 6.33 (1H, d, J=3.1 Hz), 4.02-3.97 (2H, m), 3.61 (2H, br s), 2.05 (3H, s), 1.40 (3H, t, J=7.1 Hz).

Step (3)

(702) To a mixture of 33.0 g of 3-ethoxy-2-methyl-aniline and 400 mL of toluene, 25 g of triphosgene was added at room temperature, followed by stirring while heating under reflux for 4 hours. The mixture was concentrated under reduced pressure to obtain 37.2 g of 1-ethoxy-3-isocyanate-2-methylbenzene.

(703) ##STR00343##

(704) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.07 (1H, t, J=8.2 Hz), 6.70 (1H, d, J=7.7 Hz), 6.68 (1H, d, J=8.2 Hz), 4.02 (2H, q, J=7.0 Hz), 2.20 (3H, s), 1.42 (3H, t, J=7.0 Hz).

Step (4)

(705) To a mixture of 350 mL of N,N-dimethylformamide and 33.6 g of aluminum trichloride, 15 g of sodium azide was added at 0° C., followed by stirring for one hour. Thereafter, 37.2 g of 1-ethoxy-3-isocyanate-2-methylbenzene was added and the reaction mixture was raised to 80° C., followed by stirring for 5 hours. After cooling the mixture, 100 mL of ice water was added to the reaction mixture at 0° C. and a mixture of 23 g of sodium nitrite and 150 mL of water was added. Thereafter, the pH of the mixture was adjusted to about 4 by adding 10% hydrochloric acid. After extraction with ethyl acetate, the organic layer was washed in turn with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 39.0 g of 1-(3-ethoxy-2-methylphenyl)-1,4-dihydrotetrazol-5-one.

(706) ##STR00344##

(707) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.30 (1H, t, J=8.1 Hz), 6.99 (1H, d, J=8.5 Hz), 6.96 (1H, d, J=8.0 Hz), 4.10 (2H, q, J=6.9 Hz), 2.13 (3H, s), 1.46 (3H, t, J=7.0 Hz).

Step (5)

(708) To a mixture of 400 mL of N,N-dimethylformamide, 39.0 g of the above 1-(3-ethoxy-2-methylphenyl)-1,4-dihydrotetrazol-5-one, 36.7 g of potassium carbonate, and 400 mL of N,N-dimethylformamide, 44.7 g of dimethyl sulfate was added at 0° C. and the temperature was raised to room temperature, followed by stirring for 7 hours. Water (100 mL) was added, followed by extraction with ethyl acetate. The organic layer was washed in turn with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 38.2 g of 1-(3-ethoxy-2-methylphenyl)-4-methyl-1,4-dihydrotetrazol-5-one.

(709) ##STR00345##

(710) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.29-7.23 (1H, m), 6.96 (1H, d, J=8.2 Hz), 6.93 (1H, d, J=8.2 Hz), 4.08 (2H, q, J=6.9 Hz), 3.72 (3H, s), 2.11 (3H, s), 1.45 (3H, t, J=7.1 Hz).

Step (6)

(711) A mixture of 38.2 g of 1-(3-ethoxy-2-methylphenyl)-4-methyl-1,4-dihydrotetrazol-5-one, 7.95 g of 1,1′-azobis(cyclohexane-1-carbonitrile), 33.4 g of N-bromosuccinimide, and 380 mL of chlorobenzene was stirred at 120° C. for 5 hours. After cooling, water was poured into the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed in turn with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 38.2 g of 1-(3-ethoxy-2-bromomethylphenyl)-4-methyl-1,4-dihydrotetrazol-5-one (C13A).

(712) ##STR00346##

(713) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.40 (1H, t, J=8.2 Hz), 7.01 (2H, t, J=8.3 Hz), 4.64 (2H, s), 4.17 (2H, q, J=7.0 Hz), 3.74 (3H, s), 1.49 (3H, t, J=6.9 Hz).

Reference Production Example 14

Step (1)

(714) A mixture of 29.8 g of 1-(2-methoxymethyl-3-bromophenyl)-4-methyl-1,4-dihydrotetrazol-5-one mentioned in Reference Production Example 11, 35.2 g of tributylvinyltin, 11.6 g of tetrakistriphenylphosphine palladium, and 500 mL of toluene was stirred while heating under reflux for 14 hours.

(715) After cooling, an aqueous saturated ammonium chloride solution was poured into the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed in turn with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 19.7 g of 1-(2-methoxymethyl-3-ethenylphenyl)-4-methyl-1,4-dihydrotetrazol-5-one.

(716) ##STR00347##

(717) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.67 (1H, dd, J=7.8, 1.3 Hz), 7.44 (1H, t, J=7.8 Hz), 7.29 (1H, dd, J=7.8, 1.3 Hz), 7.11 (1H, dd, J=17.4, 11.1 Hz), 5.72 (1H, dd, J=17.4, 1.3 Hz), 5.44 (1H, dd, J=11.1, 1.3 Hz), 4.45 (2H, s), 3.72 (3H, s), 3.23 (3H, s).

Step (2)

(718) A mixture of 19.7 g of 1-(2-methoxymethyl-3-ethenylphenyl)-4-methyl-1,4-dihydrotetrazol-5-one, 3.02 g of palladium-fibroin complex, and 1 L of methanol was stirred under hydrogen atmosphere at room temperature for 11 hours.

(719) The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 19.3 g of 1-(2-methoxymethyl-3-ethylphenyl)-4-methyl-1,4-dihydrotetrazol-5-one.

(720) ##STR00348##

(721) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.42-7.38 (2H, m), 7.23-7.20 (1H, m), 4.44 (2H, s), 3.72 (3H, s), 3.22 (3H, s), 2.82 (2H, q, J=7.6 Hz), 1.27 (3H, t, J=7.6 Hz).

Step (3)

(722) A mixture of 19.3 g of 1-(2-methoxymethyl-3-ethylphenyl)-4-methyl-1,4-dihydrotetrazol-5-one, 40 mL of acetic acid, and 40 mL of a 25% hydrogen bromide-acetic acid solution was stirred at 65° C. for 1.5 hours. An aqueous saturated sodium chloride solution was poured into the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with an aqueous saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain 23.3 g of 1-(2-bromomethyl-3-ethylphenyl)-4-methyl-1,4-dihydrotetrazol-5-one (C14A).

(723) ##STR00349##

(724) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.44-7.37 (2H, m), 7.23 (1H, dd, J=7.1, 2.0 Hz), 4.56 (2H, s), 3.75 (3H, s), 2.85 (2H, q, J=7.6 Hz), 1.33 (3H, t, J=7.6 Hz).

Reference Production Example 15

Step (1)

(725) A mixture of 9.4 g of sodium borohydride and 150 mL of tetrahydrofuran was stirred at 25° C. for 30 minutes. 2-methyl-3-nitrobenzoic acid (30.8 g) was added, followed by stirring at 25° C. for 30 minutes. After ice cooling of this mixed solution, 11.0 mL of methanesulfonic acid was slowly added over 45 minutes. The reaction mixture was stirred at 25° C. for 3 days. Water was poured into the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed in turn with 10% hydrochloric acid and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain 27.0 g of 3-hydroxymethyl-2-methyl-1-nitrobenzene.

(726) ##STR00350##

(727) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 1.81 (1H, s), 2.44 (3H, s), 4.79 (2H, s), 7.34 (1H, t, J=7.8 Hz), 7.65 (1H, d, 7.6 Hz), 7.72 (1H, d, J=8.1 Hz).

Step (2)

(728) A mixture of 17.0 g of 3-hydroxymethyl-2-methyl-1-nitrobenzene, 65.0 g of manganese dioxide, and 170 mL of chloroform was stirred while heating under reflux for 5 hours. The cooled reaction mixture was filtered through cerite and then concentrated under reduced pressure to obtain 14.0 g of 3-formyl-2-methyl-1-nitrobenzene.

(729) ##STR00351##

(730) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 2.78 (3H, s), 7.53 (1H, t, J=8.1 Hz), 7.97 (1H, dd, J=1.5, 8.1 Hz), 8.06 (1H, dd, J=1.5, 7.8 Hz), 10.39 (1H, s).

Step (3)

(731) While cooling a mixture of 13.0 g of 3-formyl-2-methyl-1-nitrobenzene and 200 mL of chloroform at −78° C., 31.7 g of N,N-diethylaminosulfur trifluoride was added dropwise, followed by stirring at 25° C. for 16 hours. Water was poured into the reaction mixture, followed by extraction with chloroform. The organic layer was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 6.8 g of 3-difluoromethyl-2-methyl-1-nitrobenzene.

(732) ##STR00352##

(733) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 2.54 (3H, s), 6.84 (1H, t, J=54.6 Hz), 7.45 (1H, t, J=7.7 Hz), 7.78 (1H, d, J=7.7 Hz), 7.89 (1H, d, J=8.0 Hz)

Step (4)

(734) A mixture of 6.80 g of 3-difluoromethyl-2-methyl-1-nitrobenzene, 0.30 g of 5% platinum-activated carbon, and 50 mL of methanol was stirred under hydrogen atmosphere at 35° C. for 8 hours. The reaction mixture was filtered through cerite and the filtrate was concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 3.87 g of 3-difluoromethyl-2-methyl-1-aminobenzene.

(735) ##STR00353##

(736) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 2.20 (3H, s), 3.71 (2H, s), 6.72 (1H, t, J=55.5 Hz), 6.79 (1H, d, J=8.0 Hz), 6.92 (1H, d, J=7.7 Hz), 7.09 (1H, t, J=7.7 Hz).

Step (5)

(737) A mixture of 3.87 g of 3-difluoromethyl-2-methyl-1-aminobenzene, 10.96 g of triphosgene, and 80 mL of toluene was stirred while heating under reflux for 3.5 hours. The cooled reaction mixture was concentrated under reduced pressure to obtain 3-difluoromethyl-2-methyl-1-isocyanatebenzene.

(738) ##STR00354##

(739) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 2.39 (3H, s), 6.74 (1H, t, J=55.1 Hz), 7.21-7.27 (2H, m), 7.34 (1H, d, J=7.2 Hz).

Step (6)

(740) Under ice cooling, 3.62 g of annhydrous aluminum trichloride was added to 40 mL of N,N-dimethylformamide, followed by stirring for 20 minutes. To this was added 1.76 g of sodium azide and, after stirring for 15 minutes, 3-difluoromethyl-2-methyl-1-isocyanatebenzene obtained above was added, followed by heating at 80° C. for 4 hours. After cooling, the reaction solution was added in a mixture of 6 g of sodium nitrite, 0.5 L of water, and 100 g of ice while stirring. The mixture was acidified with 10% hydrochloric acid and then extracted with ethyl acetate. The organic layer was washed in turn with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain 3.22 g of 1-(2-methyl-3-difluoromethylphenyl)-1,4-dihydrotetrazol-5-one.

(741) ##STR00355##

Step (7)

(742) A mixture of 3.22 g of 1-(2-methyl-3-difluoromethylphenyl)-1,4-dihydrotetrazol-5-one, 3.93 g of potassium carbonate, 4.04 g of methyl iodide, and 70 mL of N,N-dimethylformamide was stirred at 25° C. for 5 hours. Water was poured into the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed in turn with 10% hydrochloric acid, water, and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 1.14 g of 1-(2-methyl-3-difluoromethylphenyl)-4-methyl-1,4-dihydrotetrazol-5-one.

(743) ##STR00356##

(744) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 2.31 (3H, s), 3.73 (3H, s), 6.83 (1H, t, J=55.1 Hz), 7.44-7.46 (2H, m), 7.68-7.71 (1H, m).

Step (8)

(745) A mixture of 1.14 g of 1-(2-methyl-3-difluoromethylphenyl)-4-methyl-1,4-dihydrotetrazol-5-one, 0.23 g of 1,1′-azobis(cyclohexane-1-carbonitrile), 0.97 g of N-bromosuccinimide, and 20 mL of chlorobenzene was stirred while heating under reflux for 5 hours. After cooling, water was poured into the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed in turn with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 1.21 g of 1-(2-bromomethyl-3-difluoromethylphenyl)-4-methyl-1,4-dihydrotetrazol-5-one (C15A).

(746) ##STR00357##

(747) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 3.76 (3H, s), 4.66 (2H, s), 6.99 (1H, t, J=54.8 Hz), 7.55 (1H, d, J=8.0 Hz), 7.60 (1H, t, J=7.7 Hz), 7.56 (1H, d, J=7.5 Hz).

Reference Production Example 16

Step (1)

(748) A mixture of 7.17 g of 2-methyl-3-nitrophenol, 27 g of potassium hydroxide, 25 g of bromodifluoromethyl-diethylphosphonate, 100 mL of water, and 100 mL of acetonitrile was stirred at room temperature for 24 hours. After extraction with ethyl acetate, the organic layer was washed in turn with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 7.50 g of 1-difluoromethoxy-2-methyl-3-nitrobenzene.

(749) ##STR00358##

(750) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.74 (1H, dd, J=7.6, 1.8 Hz), 7.40-7.32 (2H, m), 6.56 (1H, t, J=72.4 Hz), 2.46 (3H, s).

Step (2)

(751) A mixture of 7.50 g of 1-difluoromethoxy-2-methyl-3-nitrobenzene, 0.8 g of palladium-carbon (palladium: 5%), and 80 mL of ethanol was stirred under hydrogen atmosphere at room temperature for 8 hours. The mixture was filtered and the filtrate was concentrated to obtain 6.4 g of

3-difluoromethoxy-2-methylaniline

(752) ##STR00359##

(753) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 6.99 (1H, t, J=8.1 Hz), 6.55 (1H, d, J=8.0 Hz), 6.51 (1H, d, J=8.2 Hz), 6.46 (1H, td, J=74.4, 0.4 Hz), 3.72 (2H, br s), 2.09 (3H, s).

Step (3)

(754) To a mixture of 6.4 g of 3-difluoromethoxy-2-methylaniline and 100 mL of toluene, 5.48 g of triphosgene was added at room temperature, followed by stirring while heating under reflux for one hour. The mixture was concentrated under reduced pressure to obtain 7.36 g of 1-difluoromethoxy-3-isocyanate-2-methylbenzene.

(755) ##STR00360##

(756) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.14 (1H, t, J=8.1 Hz), 6.97 (2H, t, J=8.5 Hz), 6.50 (1H, td, J=73.6, 0.4 Hz), 2.27 (3H, s).

Step (4)

(757) Under ice cooling, to a mixture of 200 mL of N,N-dimethylformamide and 5.91 g of anhydrous aluminum chloride, 2.64 g of sodium azide was added, followed by stirring for one hour. After the addition of 7.36 g of 1-difluoromethoxy-3-isocyanate-2-methylbenzene, the reaction mixture was raised to 75° C., followed by stirring for 9 hours. The mixture was cooled and 50 mL of ice water was added to the reaction mixture under ice cooling, followed by the addition of a mixture of 4.1 g of sodium nitrite and 100 mL of water. Thereafter, the pH of the mixture was adjusted to about 4 by adding concentrated hydrochloric acid. After extraction with ethyl acetate, the organic layer was washed in turn with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. To the obtained residue containing 1-(2-methyl-3-difluoromethoxyphenyl)-1,4-dihydrotetrazol-5-one, 100 mL of N,N-dimethylformamide, 7.66 g of potassium carbonate, and 9.32 g of dimethyl sulfate were added, followed by stirring at room temperature for 4 hours. After the addition of 100 mL of water and extraction with ethyl acetate, the organic layer was washed in turn with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 1.0 g of 1-(2-methyl-3-difluoromethoxyphenyl)-4-methyl-1,4-dihydrotetrazol-5-one.

(758) ##STR00361##

(759) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.34 (1H, t, J=8.1 Hz), 7.30-7.23 (2H, m), 6.55 (1H, t, J=72.8 Hz), 3.73 (3H, d, J=0.5 Hz), 2.21 (3H, s).

Step (5)

(760) A mixture of 1.0 g of 1-(2-methyl-3-difluoromethoxyphenyl)-4-methyl-1,4-dihydrotetrazol-5-one, 0.19 g of 1,1′-azobis(cyclohexane-1-carbonitrile), 0.80 g of N-bromosuccinimide, and 50 mL of chlorobenzene was stirred while heating under reflux for 8 hours. After cooling, water was poured into the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed in turn with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 1.1 g of 1-(2-bromomethyl-3-difluoromethoxyphenyl)-4-methyl-1,4-dihydrotetrazol-5-one (C16A).

(761) ##STR00362##

(762) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.50 (1H, t, J=8.2 Hz), 7.34 (2H, d, J=8.2 Hz), 6.62 (1H, t, J=72.8 Hz), 4.65 (2H, s), 3.76 (3H, d, J=0.5 Hz).

Reference Production Example 17

Step (1)

(763) A mixture of 30.1 g of 1-(2-methoxymethyl-3-bromophenyl)-4-methyl-1,4-dihydrotetrazol-5-one mentioned in Reference Production Example 11, 12.9 g of cyclopropylboronic acid, 46.2 g of cesium fluoride, 8.2 g of a [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct, and 680 mL of dioxane was stirred at 90° C. for 4 hours. After cooling, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 26.0 g of 1-(2-methoxymethyl-3-cyclopropylphenyl)-4-methyl-1,4-dihydrotetrazol-5-one.

(764) ##STR00363##

(765) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.36 (1H, t, J=8.0 Hz), 7.20 (2H, d, J=8.0 Hz), 4.64 (2H, s), 3.72 (3H, s), 3.24 (3H, s), 2.20-2.13 (1H, m), 1.04-1.00 (2H, m), 0.76-0.72 (2H, m).

Step (2)

(766) A mixture of 26.0 g of 1-(2-methoxymethyl-3-cyclopropylphenyl)-4-methyl-1,4-dihydrotetrazol-5-one, 40 mL of acetic acid, and 40 mL of a 25% hydrogen bromide-acetic acid solution was stirred at 65° C. for 2 hours. An aqueous saturated sodium chloride solution was poured into the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with an aqueous saturated sodium bicarbonate solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain 30.8 g of 1-(2-bromomethyl-3-cyclopropylphenyl)-4-methyl-1,4-dihydrotetrazol-5-one (C17A).

(767) ##STR00364##

(768) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.38 (1H, t, J=7.8 Hz), 7.26-7.22 (2H, m), 4.77 (2H, s), 3.75 (3H, s), 2.16-2.09 (1H, m), 1.10-1.06 (2H, m), 0.82-0.78 (2H, m).

Reference Production Example 18

Step (1)

(769) Under ice cooling, 0.63 g of 60% sodium hydride was added to a mixture of 4.99 g of triisopropylsilanethiol and 30 mL of toluene, followed by stirring for 30 minutes. To the reaction mixture, 2.82 g of 1-(2-methyl-3-bromophenyl)-4-methyl-1,4-dihydrotetrazol-5-one mentioned in Reference Production Example 5 and 0.856 g of a [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct was added, and then the temperature of the reaction mixture was raised to 90° C., followed by stirring for 4 hours.

(770) After cooling, water was poured into the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed in turn with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 3.64 g of 1-(2-methyl-3-triisopropylsilanylthiophenyl)-4-methyl-1,4-dihydrotetrazol-5-one.

(771) ##STR00365##

(772) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 1.09 (18H, d, J=6.6 Hz), 1.31 (3H, q, J=6.6 Hz), 2.45 (3H, s), 3.71 (3H, s), 7.16-7.21 (2H, m), 7.64 (1H, dd, J=6.6, 2.7 Hz).

Step (2)

(773) A mixture of 3.63 g of 1-(2-methyl-3-triisopropylsilanylthiophenyl)-4-methyl-1,4-dihydrotetrazol-5-one, 2.91 g of cesium fluoride, and 10 mL of N,N-dimethylformamide was stirred at room temperature for 30 minutes.

(774) To the mixture, 2.72 g of methyl iodide was added, followed by stirring at room temperature for 3 hours. Water was poured into the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed in turn with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 1.65 g of 1-(2-methyl-3-methylthiophenyl)-4-methyl-1,4-dihydrotetrazol-5-one

(775) ##STR00366##

(776) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 2.22 (3H, s), 2.51 (3H, s), 3.72 (3H, s), 7.10-7.16 (1H, m), 7.36-7.29 (2H, m).

Step (3)

(777) A mixture of 1.50 g of 1-(2-methyl-3-methylthiophenyl)-4-methyl-1,4-dihydrotetrazol-5-one, 0.62 g of 1,1′-azobis(cyclohexane-1-carbonitrile), 1.30 g of N-bromosuccinimide, and 15 mL of chlorobenzene was stirred while heating under reflux for 4 hours. After cooling, water was poured into the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed in turn with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 0.40 g of 1-(2-bromomethyl-3-methylthiophenyl)-4-methyl-1,4-dihydrotetrazol-5-one (C18A).

(778) ##STR00367##

(779) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 2.57 (3H, s), 3.75 (3H, s), 4.69 (2H, s), 7.20 (1H, t, J=4.5 Hz), 7.44 (2H, d, J=4.5 Hz).

Reference Production Example 19

(780) A mixture of 30 mL of ethanol, 5.0 g of 3′-bromo-4′-fluoroacetophenone, 2.4 g of hydroxylamine hydrochloride, and 4.6 mL of pyridine was stirred while heating under reflux for 4 hours. After the solvent was distilled off, hydrochloric acid (1M) was added, followed by extraction three times with ethyl acetate and further washing with a saturated saline solution. The obtained solution was dried over anhydrous magnesium sulfate and then concentrated to obtain a crude product of 1-(3-bromo-4-fluorophenyl)ethanone oxime (C19A).

(781) ##STR00368##

(782) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 9.00 (1H, bs), 7.83 (1H, dd, J=6.5, 2.2 Hz), 7.57-7.53 (1H, m), 7.12 (1H, t, J=8.5 Hz), 2.26 (3H, s).

Reference Production Examples 20 to 74

(783) In the same manner as in Reference Production Example 19, except that each raw material was used in place of a ketone compound, production was performed.

3-(1-hydroxyiminoethyl)benzonitrile (C20A)

(784) ##STR00369##

(785) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.87 (1H, s), 7.93-7.92 (1H, m), 7.88-7.85 (1H, m), 7.67-7.65 (1H, m), 7.51 (1H, t, J=7.9 Hz), 2.30 (3H, s).

1-(3-methoxyphenyl)ethanone oxime (C21A)

(786) ##STR00370##

(787) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.30 (1H, t, J=7.9 Hz), 7.20-7.16 (2H, m), 6.95-6.92 (1H, m), 3.83 (3H, s), 2.30 (3H, s).

1-(3-nitrophenyl)ethanone oxime (C22A)

(788) ##STR00371##

(789) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.50 (1H, t, J=2.0 Hz), 8.23 (1H, dq, J=8.2, 1.0 Hz), 8.00 (1H, dt, J=7.9, 1.2 Hz), 7.79 (1H, s), 7.56 (1H, t, J=8.1 Hz), 2.34 (3H, s).

1-(3,5-dimethylphenyl)ethanone oxime (C23A)

(790) ##STR00372##

(791) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.23 (2H, s), 7.02 (1H, s), 2.34 (6H, s), 2.27 (3H, s).

indan-1-one oxime (C24A)

(792) ##STR00373##

(793) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.77 (1H, d, J=7.8 Hz), 7.59 (1H, t, J=7.4 Hz), 7.49 (1H, d, J=7.8 Hz), 7.37 (1H, t, J=7.4 Hz), 3.17-3.14 (2H, m), 2.72-2.68 (2H, m).

6-methyl-indan-1-one oxime (C25A)

(794) ##STR00374##

(795) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.56 (1H, s), 7.42-7.36 (2H, m), 3.11-3.08 (2H, m), 2.70-2.68 (2H, m), 2.41 (3H, s).

1-(naphthalen-2-yl)ethanone oxime (C26A)

(796) ##STR00375##

(797) .sup.1H-NMR (DMSO-D.sub.6) δ(ppm): 11.34 (1H, s), 8.13 (1H, s), 7.99-7.97 (1H, m), 7.94-7.87 (3H, m), 7.53 (2H, t, J=4.4 Hz), 2.28 (3H, s).

1-(naphthalen-1-yl)ethanone oxime (C27A)

(798) ##STR00376##

(799) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.62 (1H, s), 8.04-8.00 (1H, m), 7.90-7.84 (2H, m), 7.55-7.44 (4H, m), 2.38 (3H, s).

1-(3-chlorophenyl)ethanone oxime (C28A)

(800) ##STR00377##

(801) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.23 (1H, s), 7.62 (1H, t, J=1.8 Hz), 7.51 (1H, dt, J=7.3, 1.6 Hz), 7.37-7.29 (2H, m), 2.27 (3H, s).

1-(2-trifluoromethylphenyl)ethanone oxime (C29A)

(802) ##STR00378##

(803) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.33 (1H, s), 7.70 (1H, d, J=7.8 Hz), 7.56 (1H, t, J=7.6 Hz), 7.49 (1H, t, J=7.7 Hz), 7.36 (1H, d, J=7.6 Hz), 2.22 (3H, s).

1-(indan-5-yl)ethanone oxime (C30A)

(804) ##STR00379##

(805) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.49 (1H, s), 7.40 (1H, d, J=8.0 Hz), 7.23 (1H, d, J=7.7 Hz), 2.92 (4H, m), 2.29 (3H, s), 2.09 (2H, m).

1-(3,5-dichlorophenyl)ethanone oxime (C31A)

(806) ##STR00380##

(807) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.06 (1H, s), 7.51 (2H, d, J=2.0 Hz), 7.36 (1H, t, J=1.8 Hz), 2.25 (3H, s).

6-chloroindan-1-one oxime (C32A)

(808) ##STR00381##

(809) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.63 (1H, d, J=2.0 Hz), 7.31 (1H, d, J=8.2, 2.1 Hz), 7.24 (1H, dd, J=8.2, 0.6 Hz), 3.05-2.97 (4H, m).

1-(3,5-ditrifluoromethylpheny)ethanone oxime (C33A)

(810) ##STR00382##

(811) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.09 (2H, s), 7.88 (1H, s), 7.86 (1H, s), 2.33 (3H, s).

1-(3-trifluoromethoxyphenyl)ethanone oxime (C34A)

(812) ##STR00383##

(813) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.38 (1H, bs), 7.56 (1H, d, J=7.7 Hz), 7.50 (1H, s), 7.41 (1H, t, J=8.0 Hz), 7.24 (1H, d, J=8.2 Hz), 2.29 (3H, s).

2,2,2-trifluoro-1-phenylethanone oxime (C35A)

(814) ##STR00384##

(815) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.53-7.40 (5H, m).

1-(4-trifluoromethylphenyl)ethanone oxime (C36A)

(816) ##STR00385##

(817) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.74 (2H, d, J=8.2 Hz), 7.64 (2H, d, J=8.2 Hz), 2.32 (3H, s).

1-(3,5-difluorophenyl)ethanone oxime (C37A)

(818) ##STR00386##

(819) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.98 (1H, s), 7.18-7.15 (2H, m), 6.82 (1H, tt, J=8.8, 2.3 Hz), 2.25 (3H, s).

3-trifluoromethylbenzaldehyde oxime (C38A)

(820) ##STR00387##

(821) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.17 (1H, s), 7.85 (1H, s), 7.75 (1H, d, J=7.6 Hz), 7.64 (1H, d, J=7.8 Hz), 7.52 (1H, m).

1-(3-trifluoromethylphenyl)propan-1-one oxime (C39A)

(822) ##STR00388##

(823) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.30 (1H, bs), 7.88 (1H, s), 7.80 (1H, d, J=7.8 Hz), 7.63 (1H, d, J=7.8 Hz), 7.51 (1H, t, J=7.9 Hz), 2.84 (2H, q, J=7.6 Hz), 1.18 (3H, t, J=7.7 Hz). 1-(benzo[1,3]dioxan-5-yl)ethanone oxime (C40A)

(824) ##STR00389##

(825) .sup.1H-NMR (DMSO-D.sub.6) δ(ppm): 11.04 (1H, bs), 7.20 (1H, d, J=1.6 Hz), 7.12 (1H, dd, J=8.1, 1.7 Hz), 6.91 (1H, d, J=8.0 Hz), 6.03 (2H, s), 2.10 (3H, s).

4-chloroindan-1-one oxime (C41A)

(826) ##STR00390##

(827) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.80 (1H, bs), 7.56 (1H, d, J=7.8 Hz), 7.34 (1H, d, J=7.8 Hz), 7.22 (1H, t, J=7.8 Hz), 3.10-3.06 (2H, m), 3.01-2.97 (2H, m).

1-(3-trifluoromethylphenyl)ethanone oxime (C42A)

(828) ##STR00391##

(829) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.97-7.90 (2H, m), 7.82 (1H, d, J=8.0 Hz), 7.63 (1H, d, J=7.7 Hz), 7.51 (1H, t, J=7.9 Hz), 2.31 (3H, s).

1-(3,4-dichlorophenyl)ethanone oxime (C43A)

(830) ##STR00392##

(831) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.78 (1H, bs), 7.73 (1H, d, J=1.8 Hz), 7.48 (1H, dd, J=8.4, 2.0 Hz), 7.44 (1H, d, J=8.5 Hz), 2.25 (3H, s).

1-(3,4-difluorophenyl)ethanone oxime (C44A)

(832) ##STR00393##

(833) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.58 (1H, bs), 7.51-7.45 (1H, m), 7.38-7.33 (1H, m), 7.20-7.13 (1H, m), 2.26 (3H, s). 1-(5,6,7,8-tetrahydronaphthalen-2-yl)ethanone oxime (C45A)

(834) ##STR00394##

(835) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.61 (1H, bs), 7.34 (1H, d, J=8.0 Hz), 7.32 (1H, s), 7.07 (1H, d, J=8.0 Hz), 2.80-2.76 (4H, m), 2.27 (3H, s), 1.83-1.78 (4H, m).

1-(3-methylphenyl)ethanone oxime (C46A)

(836) ##STR00395##

(837) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.51 (1H, bs), 7.44-7.41 (2H, m), 7.29 (1H, d, J=7.7 Hz), 7.19 (1H, d, J=7.5 Hz), 2.38 (3H, s), 2.29 (3H, s).

1-(2-trifluoromethylphenyl)propan-1-one oxime (C47A)

(838) ##STR00396##

(839) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.72-7.70 (1H, m), 7.55-7.54 (1H, m), 7.50-7.48 (1H, m), 7.32 (1H, d, J=7.6 Hz), 2.76 (2H, q, J=7.7 Hz), 1.01 (3H, t, J=7.7 Hz).

1-(4-trifluoromethylphenyl)propan-1-one oxime (C48A)

(840) ##STR00397##

(841) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.13 (1H, bs), 7.74 (2H, d, J=8.2 Hz), 7.64 (2H, d, J=8.2 Hz), 2.84 (2H, q, J=7.6 Hz), 1.18 (3H, t, J=7.6 Hz).

1-(5-fluoro-3-trifluoromethylphenyl)propan-1-one oxime (C49A)

(842) ##STR00398##

(843) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.67 (1H, s), 7.51 (1H, dt, J=9.5, 1.8 Hz), 7.34 (1H, d, J=8.2 Hz), 2.82 (2H, q, J=7.6 Hz), 1.18 (3H, t, J=7.7 Hz).

1-(3-iodophenyl)ethanone oxime (C50A)

(844) ##STR00399##

(845) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.95 (1H, bs), 7.96 (1H, s), 7.70 (1H, d, J=8.0 Hz), 7.58 (1H, d, J=7.8 Hz), 7.12 (1H, t, J=7.9 Hz), 2.26 (3H, s).

1-(3-bromophenyl)ethanone oxime (C51A)

(846) ##STR00400##

(847) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.93 (1H, bs), 7.76 (1H, t, J=1.8 Hz), 7.55 (1H, d, J=7.8 Hz), 7.51 (1H, d, J=8.0 Hz), 7.25 (1H, t, J=7.9 Hz), 2.28 (3H, s).

1-(2-methylphenyl)ethanone oxime (C52A)

(848) ##STR00401##

(849) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.26-7.20 (4H, m), 2.35 (3H, s), 2.23 (3H, s).

1-(2-chlorophenyl)ethanone oxime (C53A)

(850) ##STR00402##

(851) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.91 (1H, bs), 7.42-7.39 (1H, m), 7.33-7.29 (3H, m), 2.27 (3H, s).

1-(2-methoxyphenyl)ethanone oxime (C54A)

(852) ##STR00403##

(853) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.98 (1H, bs), 7.36-7.29 (2H, m), 6.97-6.90 (2H, m), 3.84 (3H, s), 2.24 (3H, s).

1-(3-difluoromethylphenyl)ethanone oxime (C55A)

(854) ##STR00404##

(855) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.39 (1H, s), 7.77-7.74 (2H, m), 7.54-7.46 (2H, m), 6.67 (1H, t, J=56.3 Hz), 2.32 (3H, s).

1-(2,2-difluorobenzo[1,3]dioxan-5-yl)ethanone oxime (C56A)

(856) ##STR00405##

(857) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.92 (1H, bs), 7.41 (1H, d, J=1.7 Hz), 7.34 (1H, dd, J=8.5, 1.7 Hz), 7.06 (1H, d, J=8.3 Hz), 2.27 (3H, s).

1-[3-(1,1,2,2-tetrafluoroethoxyl)phenyl]ethanone oxime (C57A)

(858) ##STR00406##

(859) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.41 (1H, bs), 7.55 (1H, dt, J=7.8, 1.3 Hz), 7.49 (1H, s), 7.40 (1H, t, J=8.1 Hz), 7.25-7.22 (1H, m), 5.92 (1H, tt, J=53.2, 2.9 Hz), 2.29 (3H, s).

1-(3-difluoromethoxyphenyl)ethanone oxime (C58A)

(860) ##STR00407##

(861) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.47-7.44 (1H, m), 7.40-7.36 (2H, m), 7.14 (1H, dd, J=7.8, 1.7 Hz), 6.54 (1H, t, J=73.8 Hz), 2.29 (3H, s).

cyclopropyl (3-trifluoromethylphenyl)methanone oxime (C59A)

(862) ##STR00408##

(863) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.74-7.46 (4H, m), 2.28-2.21 (0.7H, m), 1.76-1.70 (0.3H, m), 1.04-0.97 (1.3H, m), 0.90-0.81 (1.3H, m), 0.64 (1.4H, m).

2-methyl-1-(3-trifluoromethylphenyl)propan-1-one oxime (C60A)

(864) ##STR00409##

(865) MS, m/z: 231 (M+).

1-(3-trifluoromethylphenyl)pentan-1-one oxime (C61A)

(866) ##STR00410##

(867) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.89 (1H, s), 7.79 (1H, d, J=7.8 Hz), 7.62 (1H, d, J=7.8 Hz), 7.50 (2H, t, J=7.8 Hz), 2.84-2.80 (2H, m), 1.53-1.50 (2H, m), 1.45-1.36 (2H, m), 0.93 (3H, t, J=7.3 Hz).

1-(3-trifluoromethylphenyl)heptan-1-one oxime (C62A)

(868) ##STR00411##

(869) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.88 (1H, s), 7.78 (1H, d, J=7.6 Hz), 7.62 (1H, d, J=7.6 Hz), 7.52-7.48 (2H, m), 2.80 (2H, t, J=7.8 Hz), 1.55-1.51 (2H, m), 1.42-1.35 (2H, m), 1.30-1.27 (4H, m), 0.89-0.86 (3H, m). 3-methyl-1-(3-trifluoromethylphenyl)butan-1-one oxime (C63A)

(870) ##STR00412##

(871) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.09 (1H, bs), 7.87 (1H, s), 7.78 (1H, d, J=7.8 Hz), 7.62 (1H, d, J=7.8 Hz), 7.50 (1H, t, J=7.8 Hz), 2.76 (2H, d, J=7.6 Hz), 1.95 (1H, sep, J=6.9 Hz), 0.94 (6H, d, J=6.6 Hz). 2,2-dimethyl-1-(3-trifluoromethylphenyl)propan-1-one oxime (C64A)

(872) ##STR00413##

(873) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.63 (1H, d, J=8.1 Hz), 7.55 (1H, t, J=7.4 Hz), 7.36 (1H, s), 7.30 (1H, d, J=7.6 Hz), 7.23-7.16 (1H, m), 1.17 (9H, s).

N-[3-(1-hydroxyiminoethyl)phenyl]acetamide (C65A)

(874) ##STR00414##

(875) .sup.1H-NMR (DMSO-D.sub.6) δ(ppm): 11.21 (1H, bs), 9.99 (1H, s), 7.91 (1H, s), 7.58 (1H, t, J=7.8 Hz), 7.29-7.30 (2H, m), 2.13 (3H, s), 2.05 (3H, s).

N-[3-(1-hydroxyiminoethyl)phenyl]-N-methylacetamide (C66A)

(876) ##STR00415##

(877) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.57 (1H, d, J=7.8 Hz), 7.53-7.52 (1H, m), 7.43 (1H, t, J=7.9 Hz), 7.20 (1H, d, J=7.8 Hz), 3.29 (3H, s), 2.29 (3H, s), 1.91 (3H, s).

1-(3-hexyloxyphenyl)ethanone oxime (C67A)

(878) ##STR00416##

(879) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.81 (1H, bs), 7.30-7.26 (1H, m), 7.19-7.17 (2H, m), 6.93-6.90 (1H, m), 3.98 (2H, t, J=6.5 Hz), 2.27 (3H, s), 1.82-1.75 (2H, m), 1.50-1.43 (2H, m), 1.36-1.32 (4H, m), 0.92-0.89 (3H, m). 1-(3-isopropoxyphenyl)ethanone oxime (C68A)

(880) ##STR00417##

(881) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.29 (1H, d, J=8.2 Hz), 7.18-7.16 (2H, m), 6.92-6.89 (1H, m), 4.59 (1H, spt, J=6.1 Hz), 2.27 (3H, s), 1.35 (6H, d, J=6.2 Hz). 1-(3-pentyloxyphenyl)ethanone oxime (C69A)

(882) ##STR00418##

(883) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.45 (1H, bs), 7.30-7.28 (1H, m), 7.19-7.17 (2H, m), 6.92-6.90 (1H, m), 3.98 (2H, t, J=6.5 Hz), 2.28 (3H, s), 1.83-1.76 (2H, m), 1.48-1.34 (4H, m), 0.93 (3H, t, J=7.0 Hz). 1-(3-trifluoromethylphenyl)butan-1-one oxime (C70A)

(884) ##STR00419##

(885) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.86 (1H, s), 7.77 (1H, d, J=7.8 Hz), 7.63 (1H, d, J=7.8 Hz), 7.51 (1H, t, J=7.8 Hz), 2.81 (2H, t, J=7.8 Hz), 1.65-1.56 (2H, m), 0.99 (3H, t, J=7.4 Hz).

1-[3-(butyn-2-yloxy)phenyl]ethanone oxime (C71A)

(886) ##STR00420##

(887) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.79 (1H, bs), 7.31 (1H, t, J=8.1 Hz), 7.24-7.23 (2H, m), 7.00-6.97 (1H, m), 4.68 (2H, q, J=2.2 Hz), 2.28 (3H, s), 1.87 (3H, t, J=2.0 Hz).

1-[3-(pentyn-2-yloxy)phenyl]ethanone oxime (C72A)

(888) ##STR00421##

(889) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.30 (1H, t, J=8.1 Hz), 7.24-7.22 (2H, m), 7.01-6.98 (1H, m), 4.69 (2H, t, J=2.1 Hz), 2.29 (3H, s), 2.28-2.23 (2H, m), 1.14 (3H, t, J=7.4 Hz). 1-(3-dimethylaminophenyl)ethanone oxime (C73A)

(890) ##STR00422##

(891) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.27-7.23 (1H, m), 7.00 (1H, s), 6.94 (1H, d, J=7.8 Hz), 6.77 (1H, dd, J=8.2, 2.5 Hz), 2.98 (6H, s), 2.29 (3H, s).

1-(3-trifluoromethylphenyl)-1-hydroxyimino-2,2,2-trifluoroethane (C74A)

(892) ##STR00423##

(893) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.73-7.50 (4H, m).

Reference Production Example 75

(894) Under nitrogen atmosphere, to a mixture of 100 mL of chloroform and 1.89 g of C39A, 1.40 g of N-chlorosuccinimide was added at 0° C. and the temperature was raised to room temperature, followed by stirring for 2 hours. Water was added, followed by extraction three times with chloroform and further washing with a saturated saline solution. The obtained solution was dried over anhydrous sodium sulfate and then concentration to obtain a crude product. The crude product was subjected to silica gel column chromatography to obtain 1.86 g of α-chloro-(3-trifluoromethylbenzaldehyde)oxime (C75A).

(895) ##STR00424##

(896) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.12 (1H, s), 8.04 (1H, d, J=8.0 Hz), 7.88 (1H, s), 7.70 (1H, d, J=7.8 Hz), 7.55 (1H, t, J=7.9 Hz).

Reference Production Example 76

(897) To a mixture of tetrahydrofuran and 4.66 g of C96A, 32 mL of 1M-methylmagnesium bromide tetrahydrofuran solvent was added dropwise at 0° C., followed by stirring while heating under reflux for 4 hours and further stirring at room temperature for 10 hours. After completion of the reaction, an aqueous saturated ammonium chloride solution was added, and the mixture was extracted three times with ethyl acetate, dried over anhydrous magnesium sulfate, and then concentrated to obtain a crude product of 1-(3-difluoromethylphenyl)ethanone (C76A).

(898) ##STR00425##

(899) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.10-8.07 (2H, m), 7.73 (1H, d, J=7.6 Hz), 7.58 (1H, t, J=7.8 Hz), 6.71 (1H, t, J=56.2 Hz), 2.65 (3H, s).

Reference Production Examples 77 to 78

(900) In the same manner as in Reference Production Example 76, except that each raw material was used in place of an amide compound, production was performed.

1-(2,2-difluorobenzo[1,3]dioxol-5-yl)ethanone (C77A)

(901) ##STR00426##

(902) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.78 (1H, dd, J=8.3, 1.7 Hz), 7.69 (1H, d, J=1.7 Hz), 7.14 (1H, d, J=8.3 Hz), 2.60 (3H, s).

1-[3-(1,1,2,2-tetrafluoroethoxyl)phenyl]ethanone (C78A)

(903) ##STR00427##

(904) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.88 (1H, dt, J=7.6, 1.3 Hz), 7.79 (1H, s), 7.51 (1H, t, J=7.9 Hz), 7.44-7.41 (1H, m), 5.94 (1H, tt, J=53.1, 2.8 Hz), 2.62 (3H, s).

Reference Production Example 79

(905) To a mixture of 50 mL of acetonitrile, 50 mL of water, 10.5 g of potassium hydroxide, and 1.27 g of 3-hydroxyacetophenone, 5.0 g of bromodifluoromethyl diethylphosphonate was added dropwise at −78° C.

(906) The temperature was raised to room temperature, followed by stirring for 3 hours. After completion of the reaction, the reaction solution was extracted with ethyl acetate and the obtained crude product was subjected to silica gel column chromatography to obtain 1-(3-difluoromethylphenyl)ethanone (C79A).

(907) ##STR00428##

(908) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.80 (1H, dt, J=7.8, 1.2 Hz), 7.70 (1H, t, J=1.7 Hz), 7.48 (1H, t, J=7.9 Hz), 7.34 (1H, dd, J=8.2, 2.1 Hz), 6.57 (1H, t, J=73.3 Hz), 2.61 (3H, s).

Reference Production Example 80

(909) Under nitrogen atmosphere, to a mixture of 200 mL of tetrahydrofuran and 4.66 g of C99A, 80 mL of a 0.5M-cyclopropylmagnesium bromide-tetrahydrofuran solution was added dropwise at 0° C., followed by stirring for 2 hours. After completion of the reaction, an aqueous saturated ammonium chloride solution was added, and the mixture was extracted three times with ethyl acetate, dried over anhydrous magnesium sulfate, and then concentration to obtain a crude product.

(910) The obtained crude product was subjected to silica gel column chromatography to obtain 0.55 g of cyclopropyl(3-trifluoromethylphenyl)methanone (C80A).

(911) ##STR00429##

(912) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.26 (1H, s), 8.19 (1H, d, J=7.8 Hz), 7.82 (1H, d, J=7.8 Hz), 7.62 (1H, t, J=7.9 Hz), 2.71-2.63 (1H, m), 1.32-1.28 (2H, m), 1.14-1.10 (2H, m).

Reference Production Examples 81 to 85

(913) In the same manner as in Reference Production Example 80, except that each raw material was used in place of a Grignard reagent, production was performed.

2-methyl-1-(3-trifluoromethylphenyl)propan-1-one (C81A)

(914) ##STR00430##

(915) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.20 (1H, s), 8.14 (1H, d, J=7.9 Hz), 7.82 (1H, d, J=7.8 Hz), 7.62 (1H, t, J=7.9 Hz), 3.56 (1H, sep, J=7.9 Hz), 1.24 (6H, d, J=7.9 Hz) 1-(3-trifluoromethylphenyl)butan-1-one (C82A)

(916) ##STR00431##

(917) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.21 (1H, s), 8.14 (1H, d, J=7.8 Hz), 7.81 (1H, d, J=7.8 Hz), 7.61 (1H, t, J=7.8 Hz), 2.98 (2H, t, J=7.3 Hz), 1.84-1.76 (2H, m), 1.02 (3H, t, J=7.4 Hz). 1-(3-trifluoromethylphenyl)pentan-1-one (C83A)

(918) ##STR00432##

(919) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.21 (1H, s), 8.14 (1H, d, J=7.8 Hz), 7.81 (1H, d, J=7.1 Hz), 7.61 (1H, t, J=7.8 Hz), 3.00 (2H, t, J=7.3 Hz), 1.76-1.70 (2H, m), 1.47-1.38 (2H, m), 0.97 (3H, t, J=7.4 Hz).

1-(3-trifluoromethylphenyl)heptan-1-one (C84A)

(920) ##STR00433##

(921) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.20 (1H, s), 8.14 (1H, d, J=8.0 Hz), 7.81 (1H, d, J=7.8 Hz), 7.61 (1H, t, J=7.9 Hz), 2.99 (2H, t, J=7.4 Hz), 1.79-1.71 (2H, m), 1.43-1.30 (6H, m), 0.92-0.88 (3H, m). 3-methyl-1-(3-trifluoromethylphenyl)butan-1-one (C85A)

(922) ##STR00434##

(923) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.20 (1H, s), 8.13 (1H, d, J=8.0 Hz), 7.81 (1H, d, J=7.8 Hz), 7.61 (1H, t, J=7.8 Hz), 2.87 (2H, d, J=6.8 Hz), 2.31 (1H, sep, J=6.8 Hz), 1.02 (6H, d, J=6.8 Hz).

Reference Production Example 86

(924) Under nitrogen atmosphere, to a mixture of 30 mL of tetrahydrofuran and 0.73 g of magnesium, 4.2 mL of 1-bromo-3-trifluoromethylbenzene was slowly added dropwise at 0° C., followed by stirring at room temperature for one hour. The obtained solution was slowly added dropwise in a three-necked flask containing 4.7 g of pivaloyl chloride and 50 mL of tetrahydrofuran at 0° C., followed by stirring for one hour. After completion of the reaction, an aqueous saturated ammonium chloride solution was added, and the mixture was extracted three times with ethyl acetate, dried over anhydrous sodium sulfate, and then dried under reduced pressure to obtain a crude product.

(925) The obtained crude product was subjected to silica gel column chromatography to obtain 1.10 g of 2,2-dimethyl-1-(3-trifluoromethylphenyl)propan-1-one (C86A).

(926) ##STR00435##

(927) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.92 (1H, s), 7.86 (1H, d, J=7.1 Hz), 7.72 (1H, d, J=7.8 Hz), 7.54 (1H, t, J=7.8 Hz), 1.36 (9H, s).

Reference Production Example 87

(928) To a mixture of 50 mL of toluene and 6.76 g of 3-aminoacetophenone, 4.7 mL of acetic anhydride was added dropwise, followed by stirring at room temperature for 2 hours and further heating and stirring at 55° C. for one hour.

(929) After cooling to room temperature, filtration, and washing with toluene, the obtained residue was dried under reduced pressure to obtain 6.39 g of N-(3-acetylphenyl)acetamide (C87A).

(930) ##STR00436##

(931) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.00 (1H, s), 7.92 (1H, d, J=8.2 Hz), 7.69 (1H, d, J=7.8 Hz), 7.61 (1H, bs), 7.43 (1H, t, J=7.9 Hz), 2.61 (3H, s), 2.22 (3H, s).

Reference Production Example 88

(932) Under nitrogen atmosphere, a mixture of 30 mL of toluene, 3.54 g of C87A, and 1.20 g of sodium hydroxide was stirred at room temperature. Here, methyl p-toluenesulfonate was added dropwise and the reaction was performed at 60° C. for 8 hours. After cooling to room temperature, water and an aqueous sodium sulfate solution were added, and the reaction solution was extracted three times with ethyl acetate, dried over anhydrous magnesium sulfate, and then concentrated to obtain a crude product of N-(3-acetylphenyl)-N-methylacetamide (C88A).

(933) ##STR00437##

(934) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.92 (1H, s, J=7.9 Hz), 7.79 (1H, s), 7.54 (1H, t, J=7.9 Hz), 7.61 (1H, m), 3.29 (3H, s), 2.63 (3H, s), 1.88 (3H, s).

Reference Production Example 89

(935) A mixture of 30 mL of acetonitrile, 3.45 g of 3-hydroxyacetophenone, 4.81 g of 1-bromohexane, and 3.45 g of potassium carbonate was stirred while heating under reflux for 6 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentration to obtain 5.21 g of 1-(3-hexyloxyphenyl)ethanone (C89A).

(936) ##STR00438##

(937) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.52 (1H, d, J=7.6 Hz), 7.48 (1H, d, J=2.5 Hz), 7.36 (1H, t, J=8.0 Hz), 7.10 (1H, dd, J=8.2, 2.3 Hz), 4.00 (2H, t, J=6.5 Hz), 2.60 (3H, s), 1.83-1.76 (2H, m), 1.51-1.43 (2H, m), 1.37-1.32 (4H, m), 0.93-0.89 (3H, m).

Reference Production Examples 90 to 91 and 93 to 94

(938) In the same manner as in Reference Production Example 89, except that each raw material was used in place of a halogen compound, production was performed.

1-(3-isopropoxyphenyl)ethanone (C90A)

(939) ##STR00439##

(940) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.52-7.47 (2H, m), 7.35 (1H, t, J=7.9 Hz), 7.09 (1H, dd, J=8.2, 1.8 Hz), 4.63 (1H, sep, J=6.1 Hz), 2.59 (3H, s), 1.35 (6H, d, J=6.0 Hz).

1-(3-pentloxphenyl)ethanone (C91A)

(941) ##STR00440##

(942) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.52 (1H, dt, J=7.7, 1.2 Hz), 7.48 (1H, dd, J=2.1, 1.0 Hz), 7.36 (1H, t, J=7.9 Hz), 7.10 (1H, dq, J=8.2, 1.1 Hz), 4.00 (2H, t, J=6.5 Hz), 2.60 (3H, s), 1.84-1.77 (2H, m), 1.49-1.34 (4H, m), 0.94 (3H, t, J=7.1 Hz).

1-[3-(butyn-2-yloxy)phenyl]ethanone (C93A)

(943) ##STR00441##

(944) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.58-7.54 (2H, m), 7.38 (1H, t, J=7.9 Hz), 7.17 (1H, dq, J=8.2, 1.1 Hz), 4.70 (2H, q, J=2.3 Hz), 2.60 (3H, s), 1.87 (3H, t, J=2.3 Hz).

1-[3-(pentyn-2-yloxy)phenyl]ethanone (C94A)

(945) ##STR00442##

(946) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.58-7.56 (2H, m), 7.38 (1H, t, J=7.9 Hz), 7.19-7.16 (1H, m), 4.72 (2H, t, J=2.2 Hz), 2.60 (3H, s), 2.27-2.21 (2H, m), 1.14 (3H, t, J=7.4 Hz).

Reference Production Example 92

(947) In the same manner as in Reference Production Example 19, except that a raw material was used in place of a ketone compound, production was performed.

1-(benzo[1,3]dioxan-4-yl)ethanone oxime (C92A)

(948) ##STR00443##

(949) .sup.1H-NMR (CDCl.sub.3) δ: 7.02 (1H, dd, J=7.0, 2.3 Hz), 6.88-6.83 (2H, m), 6.03 (2H, s), 2.31 (3H, s).

Reference Production Example 95

(950) In the same manner as in Reference Production Example 76, except that a raw material was used in place of an amide compound, production was performed.

1-(benzo[1,3]dioxan-4-yl)ethanone oxime (C95A)

(951) ##STR00444##

(952) .sup.1H-NMR (CDCl.sub.3) δ: 7.38 (1H, dd, J=8.3, 1.2 Hz), 6.99 (1H, dd, J=7.6, 1.2 Hz), 6.89 (1H, t, J=7.9 Hz), 6.10 (2H, s), 2.61 (3H, s).

Reference Production Example 96

(953) To a mixture of 100 mL of tetrahydrofuran, 3.89 g of C100A, a catalytic amount of DMF, 3.16 g of oxalylchloride was added dropwise at 0° C. After reacting at room temperature for one hour, the solvent was distilled off under reduced pressure. To this were added chloroform, 2.65 g of N,O-dimethylhydroxylamine hydrochloride, and 7.01 g of diisopropylamine, and the mixture was reacted at room temperature for 13 hours. After completion of the reaction, water was added and the reaction solution was stirred and then extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and then concentrated to obtain

3-difluoromethyl-N-methoxy-N-methylbenzamide (C96A)

(954) ##STR00445##

(955) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.84 (1H, s), 7.81 (1H, d, J=7.6 Hz), 7.62 (1H, t, J=3.9 Hz), 7.51 (1H, t, J=7.7 Hz), 6.68 (1H, t, J=56.3 Hz), 3.55 (3H, s), 3.38 (3H, s).

Reference Production Examples 97 to 98

(956) In the same manner as in Reference Production Example 96, except that each raw material was used in place of carboxylic acid compound, production was performed.

N-methoxy-N-methyl-2,2-difluorobenzo[1,3]dioxane-5-carboxylic acid amide (C97A)

(957) ##STR00446##

(958) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.55 (1H, dd, J=8.3, 1.5 Hz), 7.49 (1H, d, J=1.7 Hz), 7.09 (1H, d, J=8.3 Hz), 3.55 (3H, s), 3.37 (3H, s).

N-methoxy-N-methyl-3-(1,1,2,2-tetrafluoroethoxyl)benzamide (C98A)

(959) ##STR00447##

(960) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.62 (1H, d, J=7.8 Hz), 7.57 (1H, s), 7.44 (1H, t, J=7.9 Hz), 7.33-7.30 (1H, m), 5.93 (1H, tt, J=53.1, 2.8 Hz), 3.56 (3H, s), 3.37 (3H, s).

Reference Production Example 99

(961) Under nitrogen atmosphere, to a mixture of 16.09 g of N,O-dimethylhydroxylamine hydrochloride in 300 mL of chloroform, 34.41 g of 3-trifluoromethyl benzoyl chloride was added dropwise at 0° C. and 50 mL of triethylamine was subsequently added dropwise. After stirring for 30 minutes while maintaining at 0° C., the temperature was raised to room temperature, followed by stirring for 4 hours. After completion of the reaction, the reaction solution was washed twice with hydrochloric acid (1M), washed twice with an aqueous sodium hydrogen carbonate solution, and further washed once with a saturated saline solution. The organic layer was dried over anhydrous sodium sulfate and then concentrated to obtain a crude product of N-methoxy-N-methyl-3-trifluoromethylbenzamide (C99A).

(962) ##STR00448##

(963) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.97 (1H, s), 7.89 (1H, d, J=7.8 Hz), 7.72 (1H, d, J=7.8 Hz), 7.55 (1H, t, J=7.8 Hz), 3.55 (3H, s), 3.39 (3H, s).

Reference Production Example 100

(964) 3-difluoromethylbenzonitrile (3.80 g) was heated and stirred in an aqueous sodium hydroxide solution for 6 hours. After cooling to room temperature, an aqueous solution prepared by adding ice water to hydrochloric acid was poured thereinto, and the precipitated solid was filtered and then dried to obtain 3-difluoromethylbenzoic acid (C100A).

(965) ##STR00449##

(966) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.27 (1H, s), 8.24 (1H, d, J=7.8 Hz), 7.79 (1H, d, J=7.8 Hz), 7.61 (1H, t, J=7.8 Hz), 6.72 (1H, t, J=56.2 Hz).

Reference Production Examples 101 to 121

(967) In the same manner as in Reference Production Example 19, except that each raw material was used in place of a ketone compound, production was performed.

1-(indan-4-yl)ethanone oxime (C101A)

(968) ##STR00450##

(969) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 9.89 (1H, bs), 7.30-7.27 (1H, m), 7.18-7.15 (2H, m), 2.97 (2H, t, J=7.4 Hz), 2.92 (2H, t, J=7.4 Hz), 2.33 (3H, s), 2.09-2.02 (2H, m).

1-(3-trifluoromethoxyphenyl)propan-1-one oxime (C102A)

(970) ##STR00451##

(971) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.20 (1H, bs), 7.56-7.54 (1H, m), 7.49 (1H, s), 7.42 (1H, t, J=8.0 Hz), 7.25-7.22 (1H, m), 2.81 (2H, q, J=7.6 Hz), 1.18 (3H, t, J=7.6 Hz).

1-(3-methylsulfanylphenyl)ethanone oxime (C103A)

(972) ##STR00452##

(973) .sup.1H-NMR (DMSO-D.sub.6) δ(ppm): 7.49 (1H, t, J=1.7 Hz), 7.41 (1H, dt, J=7.6, 1.4 Hz), 7.33 (1H, t, J=7.7 Hz), 7.26 (1H, dq, J=7.8, 1.0 Hz), 2.49 (3H, s), 2.14 (3H, s).

1-(4-cyclopropyl-3-trifluoromethylphenyl)ethanone oxime (C104A)

(974) ##STR00453##

(975) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.88 (1H, s), 7.68 (1H, d, J=8.2 Hz), 7.01 (1H, d, J=8.2 Hz), 2.26 (3H, s), 2.23-2.18 (1H, m), 1.09-1.04 (2H, m), 0.81-0.77 (2H, m).

1-(5,6,7,8-tetrahydronaphthalen-1-yl)propan-1-one oxime (C105A)

(976) ##STR00454##

(977) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.13 (1H, bs), 7.12-7.06 (2H, m), 6.97 (1H, dd, J=6.9, 1.8 Hz), 2.82-2.78 (2H, m), 2.70-2.66 (2H, m), 2.68 (2H, q, J=7.6 Hz), 1.79-1.76 (4H, m), 1.02 (3H, t, J=7.6 Hz).

1-(5,6,7,8-tetrahydronaphthalen-1-yl)ethanone oxime (C106A)

(978) ##STR00455##

(979) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.92 (1H, bs), 7.13-7.00 (3H, m), 2.82-2.79 (2H, m), 2.74-2.70 (2H, m), 2.18 (3H, s), 1.81-1.77 (4H, m).

1-(2,3-dimethylphenyl)ethanone oxime (C107A)

(980) ##STR00456##

(981) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.15 (1H, d, J=5.0 Hz), 7.14 (1H, bs), 7.10 (1H, t, J=7.4 Hz), 7.05 (1H, d, J=7.4 Hz), 2.29 (3H, s), 2.22 (3H, s), 2.20 (3H, s).

1-(3-chloro-2-methylphenyl)ethanone oxime (C108A)

(982) ##STR00457##

(983) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.64 (0.3H, bs), 7.38-7.35 (1.4H, m), 7.21-7.09 (2.0H, m), 6.98 (0.3H, d, J=8.0 Hz), 2.35 (2.0H, s), 2.28 (1.0H, s), 2.20 (2.0H, s), 2.14 (1.0H, s).

1-(2,2-difluorobenzo[1,3]dioxan-4-yl)ethanone oxime (C109A)

(984) ##STR00458##

(985) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.29 (1H, dd, J=7.8, 1.6 Hz), 7.12-7.05 (2H, m), 2.33 (3H, s).

1-(7-methoxyindan-4-yl)ethanone oxime (C110A)

(986) ##STR00459##

(987) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.22 (1H, d, J=8.5 Hz), 6.70 (1H, d, J=8.2 Hz), 3.85 (3H, s), 3.04 (2H, t, J=7.3 Hz), 2.86 (2H, t, J=7.4 Hz), 2.25 (3H, s), 2.09-2.02 (2H, m). 1-(4-methoxy-3-trifluoromethylphenyl)ethanone oxime (C111A)

(988) ##STR00460##

(989) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.88 (1H, d, J=2.3 Hz), 7.78 (1H, dd, J=8.7, 2.3 Hz), 7.00 (1H, d, J=8.7 Hz), 3.93 (3H, s), 2.26 (3H, s). 1-(2-methyl-3-trifluoromethylphenyl)ethanone oxime (C112A)

(990) ##STR00461##

(991) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.64 (1.0H, d, J=7.6 Hz), 7.37-7.23 (2.0H, m), 2.42 (1.9H, d, J=1.60 Hz), 2.36 (1.1H, d, J=1.6 Hz), 2.21 (1.9H, s), 2.16 (1.1H, s). 1-(3-cyclopropyl-2-methylphenyl)ethanone oxime (C113A)

(992) ##STR00462##

(993) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.19-7.10 (1.0H, m), 7.05-7.01 (1.7H, m), 6.91 (0.3H, d, J=7.8 Hz), 2.39 (2.2H, s), 2.32 (0.8H, s), 2.21 (2.2H, s), 2.15 (0.8H, s), 1.94-1.85 (1.0H, m), 0.96-0.91 (2.0H, m), 0.65-0.61 (2.0H, m).

1-(3-ethyl-2-methylphenyl)ethanone oxime (C114A)

(994) ##STR00463##

(995) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.21-7.13 (2.0H, m), 7.04 (0.7H, dd, J=6.8, 2.1 Hz), 6.92 (0.3H, dd, J=6.8, 2.1 Hz), 2.70-2.63 (2.0H, m), 2.25 (2.1H, s), 2.20 (2.1H, s), 2.19 (0.9H, s), 2.15 (0.9H, s), 1.25-1.19 (3.0H, m).

1-(2,5-dimethylphenyl)ethanone oxime (C115A)

(996) ##STR00464##

(997) .sup.1H-NMR (CDCl.sub.3) δ: 8.86 (1H, bs), 7.10-7.04 (3H, m), 2.31 (3H, s), 2.30 (3H, s), 2.20 (3H, s). 1-(2,2-dimethyl-2,3-dihydrobenzofuran-4-yl)ethanone oxime (C116A)

(998) ##STR00465##

(999) .sup.1H-NMR (CDCl.sub.3) δ: 7.19 (1H, bs), 7.15 (1H, t, J=7.9 Hz), 6.95 (1H, dd, J=7.9, 0.8 Hz), 6.75 (1H, d, J=8.0 Hz), 3.18 (2H, s), 2.26 (3H, s), 1.47 (6H, s).

1-(2-fluoro-3-trifluoromethylphenyl)ethanone oxime (C117A)

(1000) ##STR00466##

(1001) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.83 (0.5H, dd, J=14.7, 7.7 Hz), 7.68-7.61 (1.5H, m), 7.45-7.41 (0.3H, m), 7.28-7.24 (0.7H, m), 2.64 (0.8H, s), 2.31 (2.2H, d, J=2.7 Hz).

1-biphenyl-2-ylethanone oxime (C118A)

(1002) ##STR00467##

(1003) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.87 (1H, bs), 7.47-7.28 (9H, m), 1.68 (3H, s).

1-(dihydrobenzofuran-4-yl)ethanone oxime (C119A)

(1004) ##STR00468##

(1005) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.70 (1H, bs), 7.16 (1H, t, J=7.9 Hz), 6.97 (1H, dd, J=7.9, 0.9 Hz), 6.81 (1H, d, J=7.9 Hz), 4.56 (2H, t, J=8.7 Hz), 3.36 (2H, t, J=8.7 Hz), 2.27 (3H, s).

1-biphenyl-3-ylethanone oxime (C120A)

(1006) ##STR00469##

(1007) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.36-7.31 (4H, m), 7.29-7.26 (1H, m), 7.28 (1H, d, J=5.0 Hz), 7.11 (1H, t, J=7.1 Hz), 7.02-6.98 (3H, m), 2.23 (3H, s).

1-(4-phenyl-3-trifluoromethylphenyl)ethanone oxime (C121A)

(1008) ##STR00470##

(1009) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.03 (1H, bs), 7.82 (1H, dd, J=8.0, 1.4 Hz), 7.42-7.32 (7H, m), 2.34 (3H, s).

Reference Production Example 122

(1010) In the same manner as in Reference Production Example 76, except that a raw material was used in place of an amide compound, production was performed.

1-(3-trifluoromethoxyphenyl)propan-1-one (C122A)

(1011) ##STR00471##

(1012) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.90 (1H, dt, J=7.6, 1.3 Hz), 7.81 (1H, s), 7.51 (1H, t, J=8.0 Hz), 7.43-7.40 (1H, m), 3.01 (2H, q, J=7.2 Hz), 1.24 (3H, t, J=7.2 Hz).

Reference Production Example 123

(1013) A mixture of 0.46 g of 1-(3-sulfanylphenyl)ethanone, 0.12 g of sodium hydroxide, and 5 mL of ethanol was stirred at room temperature for one hour and then 0.43 g of iodomethane was added, followed by stirring for 2 hours. After completion of the reaction, an aqueous saturated sodium hydrogen carbonate solution was added, followed by stirring and further extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated to obtain a crude product of 1-(3-methylsulfanylphenyl)ethanone (C123A).

(1014) ##STR00472##

(1015) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.83 (1H, s), 7.70 (1H, dd, J=7.6, 1.4 Hz), 7.46-7.43 (1H, m), 7.40-7.36 (1H, m), 2.61 (3H, s), 2.54 (3H, s).

Reference Production Example 124

(1016) A mixture of 0.45 g of 1-(4-chloro-3-trifluoromethylphenyl)ethanone, 0.22 g of cyclopropylboronic acid, 0.02 g of palladium acetate, 0.06 g of tricyclohexylphosphine, 1.49 g of potassiumphosphate, 10 mL of toluene, and 0.5 mL of water was reacted by heating under reflux for 5 hours and the thus obtained crude product was subjected to silica gel column chromatography to obtain 4′-cyclopropyl-3′-trifluoromethylacetophenone (C124A).

(1017) ##STR00473##

(1018) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.19 (1H, s), 8.01 (1H, d, J=7.8 Hz), 7.07 (1H, d, J=8.2 Hz), 2.61 (3H, s), 2.31-2.24 (1H, m), 1.18-1.13 (2H, m), 0.88-0.86 (2H, m).

Reference Production Examples 125 to 128

(1019) In the same manner as in Reference Production Example 76, except that each raw material was used in place of an amide compound, production was performed.

1-(5,6,7A-tetrahydronaphthalen-1-yl)propan-1-one (C125A)

(1020) ##STR00474##

(1021) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.33 (1H, dd, J=7.1, 2.1 Hz), 7.18-7.12 (2H, m), 2.89-2.80 (6H, m), 1.81-1.73 (4H, m), 1.18 (3H, t, J=7.3 Hz).

1-(5,6,7,8-tetrahydronaphthalen-1-yl)ethanone (C126A)

(1022) ##STR00475##

(1023) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.43 (1H, d, J=7.5 Hz), 7.20-7.09 (2H, m), 2.96-2.93 (2H, m), 2.83-2.79 (2H, m), 2.55 (3H, s), 1.81-1.74 (4H, m).

3′-chloro-2′-methylacetophenone (C127A)

(1024) ##STR00476##

(1025) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.46 (2H, t, J=7.7 Hz), 7.20 (1H, t, J=7.9 Hz), 2.57 (3H, s), 2.49 (3H, s).

1-(2,2-difluorobenzo[1,3]dioxan-4-yl)ethanone (C128A)

(1026) ##STR00477##

(1027) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.64 (1H, dd, J=8.2, 1.4 Hz), 7.27-7.25 (1H, m), 7.17 (1H, t, J=8.0 Hz), 2.67 (3H, s).

Reference Production Example 129

(1028) To a mixture of 0.6 g of C141A, 2.67 g of aluminum chloride, and 20 mL of nitromethane, 0.78 g of acetyl chloride was added dropwise at 0° C., followed by stirring at room temperature for 13 hours. After completion of the reaction and cooling again to 0° C., water was added and the reaction solution was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The obtained crude product was subjected to silica gel column chromatography to obtain 1-(7-methoxyindan-4-yl)ethanone (C129A).

(1029) ##STR00478##

(1030) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.75 (1H, d, J=8.5 Hz), 6.72 (1H, d, J=8.5 Hz), 3.89 (3H, s), 3.29 (2H, t, J=7.6 Hz), 2.83 (2H, t, J=7.6 Hz), 2.55 (3H, s), 2.12-2.04 (2H, m).

Reference Production Example 130

(1031) To a mixture of 1.0 g of 1-(4-hydroxy-3-trifluoromethylphenyl)ethanone, 0.18 g of sodium hydride, and 15 mL of dimethylformamide, 0.92 g of methyl iodide was added dropwise at 0° C., followed by stirring for 3 hours. After completion of the reaction, water was added and the reaction solution was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain a crude product of 4′-methoxy-3′-trifluoromethylacetophenone (C130A).

(1032) ##STR00479##

(1033) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.20 (1H, d, J=2.1 Hz), 8.15 (1H, dd, J=8.7, 2.1 Hz), 7.06 (1H, d, J=8.7 Hz), 3.99 (3H, s), 2.60 (3H, s).

Reference Production Example 131

(1034) In the same manner as in Reference Production Example 76, except that a raw material was used in place of an amide compound, production was performed.

2′-methyl-3′-trifluoromethylacetophenone (C131A)

(1035) ##STR00480##

(1036) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.73 (1H, d, J=7.8 Hz), 7.65 (1H, d, J=7.8 Hz), 7.36 (1H, t, J=7.8 Hz), 2.59 (3H, s), 2.53 (3H, d, J=1.4 Hz).

Reference Production Example 132

(1037) In the same manner as in Reference Production Example 124, except that a raw material was used in place of a ketone compound, production was performed.

3-cyclopropyl-2-methylacetophenone (C132A)

(1038) ##STR00481##

(1039) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.40-7.36 (1H, m), 7.16 (2H, d, J=4.6 Hz), 2.57 (3H, s), 2.52 (3H, s), 1.94-1.87 (1H, m), 0.99-0.94 (2H, m), 0.65-0.61 (2H, m).

Reference Production Example 133

(1040) A mixture of 1.07 g of 3-ethyl-2-methylacetophenone, 0.73 g of ethylboronic acid, 0.61 g of a 1,1′-bis-diphenylhosphinoferrocene palladium (III) dichloride-dichloromethane complex, 3.18 g of potassium phosphate, 30 mL of 1,4-dioxane, and 3 mL of water was reacted while heating under reflux for 5 hours. The obtained crude product was subjected to silica gel column chromatography to obtain

3′-ethyl-2′-methylacetophenone (C133A)

(1041) ##STR00482##

(1042) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.39 (1H, d, J=7.6 Hz), 7.28 (1H, d, J=7.6 Hz), 7.19 (1H, t, J=7.6 Hz), 2.69 (2H, q, J=7.6 Hz), 2.56 (3H, s), 2.38 (3H, s), 1.21 (3H, t, J=7.6 Hz).

Reference Production Example 134

(1043) In the same manner as in Reference Production Example 76, except that a raw material was used in place of an amide compound, production was performed.

2′-fluoro-3′-trifluoromethylacetophenone (C134A)

(1044) ##STR00483##

(1045) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.11-8.07 (1H, m), 7.83-7.79 (1H, m), 7.35 (1H, t, J=7.8 Hz), 2.70 (3H, d, J=5.2 Hz).

Reference Production Example 135

(1046) A mixture of 1.62 g of C145A, 1.07 g of benzylamine, 10 g of 4A molecular sieves, and 30 mL of toluene was reacted while heating under reflux for 18 hours. After cooling to room temperature, the reaction mixture was filtered and the filtrate was concentrated. To the obtained crude product, 0.93 g of chlorotristriphenylphosphine rhodium and 30 mL of toluene were added, followed by stirring while heating under reflux for 12 hours. After cooling to room temperature, 1N hydrochloric acid was added and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The obtained crude product was subjected to silica gel column chromatography to obtain 0.86 g of 1-(dihydrobenzofuran-4-yl)ethanone (C135A).

(1047) ##STR00484##

(1048) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.38 (1H, dd, J=7.9, 0.9 Hz), 7.22 (1H, t, J=7.8 Hz), 6.98 (1H, d, J=7.9 Hz), 4.61 (2H, t, J=8.8 Hz), 3.55 (2H, t, J=8.8 Hz), 2.59 (3H, s).

Reference Production Example 136

(1049) A mixture of 0.45 g of 1-(4-chloro-3-trifluoromethylphenyl)ethanone, 0.22 g of phenylboronic acid, 0.02 g of palladium acetate, 2-(dichlorohexylphosphino)-2′,4′, 0.03 g of 6′-triisopropyl-1,1′-biphenyl, 0.52 g of potassium fluoride, and 5 mL of tetrahydrofuran was reacted while heating under reflux for 15 hours. The obtained crude product was subjected to silica gel column chromatography to obtain 1-(4-phenyl-3-trifluoromethylphenyl)ethanone (C136A).

(1050) ##STR00485##

(1051) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.34 (1H, s), 8.13 (1H, d, J=7.9 Hz), 7.47-7.41 (4H, m), 7.33-7.31 (2H, m), 2.67 (3H, s).

Reference Production Example 137

(1052) In the same manner as in Reference Production Example 99, except that a raw material was used in place of a halogenated acyl compound, production was performed.

N-methoxy-N-methyl-3-trifluoromethoxybenzamide (C137A)

(1053) ##STR00486##

(1054) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.64 (1H, dt, J=7.7, 1.2 Hz), 7.58 (1H, s), 7.45 (1H, t, J=8.0 Hz), 7.34-7.30 (1H, m), 3.55 (3H, s), 3.38 (3H, s).

Reference Production Examples 138 to 139

(1055) In the same manner as in Reference Production Example 96, except that each raw material was used in place of a carboxylic acid compound, production was performed.

N-methoxy-N-methyl-5,6,7,8-tetrahydronaphthalene-1-carboxylic acid amide (C138A)

(1056) ##STR00487##

(1057) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.13-7.04 (3H, m), 3.47 (3H, bs), 3.31 (3H, bs), 2.81-2.70 (4H, m), 1.81-1.78 (4H, m).

3-chloro-N-methoxy-2, N-dimethylbenzamide (C139A)

(1058) ##STR00488##

(1059) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.40-7.38 (1H, m), 7.18-7.16 (2H, m), 3.41 (3H, bs), 3.38 (3H, bs), 2.34 (3H, s).

Reference Production Example 140

(1060) A mixture of 2.0 g of 2,2-difluorobenzo[1,3]dioxane-4-carboxylic acid and 10 mL of thionyl chloride was stirred while heating under reflux for 3 hours, and then the solvent was distilled off under reduced pressure. To this were added chloroform, 1.07 g of N,O-dimethylhydroxylamine hydrochloride, and 3 mL of triethylamine, followed by stirring at room temperature for 13 hours. After completion of the reaction, an aqueous saturated sodium hydrogen carbonate solution was added, followed by stirring and further extraction with chloroform. The organic layer was dried over anhydrous sodium sulfate and then concentrated to obtain a crude product. The obtained crude product was subjected to silica gel column chromatography to obtain N-methoxy-N-methyl-2,2-difluorobenzo[1,3]dioxane-4-carboxylic acid amide (C140A).

(1061) ##STR00489##

(1062) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.29-7.25 (1H, m), 7.15-7.12 (2H, m), 3.63 (3H, s), 3.38 (3H, s).

Reference Production Example 141

(1063) To a mixture of 1.62 g of C146A and 8 mL of triethylsilane, 20 mL of trifluoroacetic acid was added dropwise at 0° C., followed by stirring while heating under reflux for 2 hours. After completion of the reaction, water was added, followed by stirring and further extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated to obtain a crude product. The obtained crude product was subjected to silica gel column chromatography to obtain 4-methoxyindane (C141A).

(1064) ##STR00490##

(1065) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.13 (1H, t, J=7.8 Hz), 6.86 (1H, d, J=7.6 Hz), 6.67 (1H, d, J=8.0 Hz), 3.83 (3H, s), 2.92 (2H, t, J=7.4 Hz), 2.87 (2H, t, J=7.4 Hz), 2.11-2.03 (2H, m).

Reference Production Example 142

(1066) In the same manner as in Reference Production Example 140, except that a raw material was used in place of a carboxylic acid compound, production was performed.

N-methoxy-2, N-dimethyl-3-trifluoromethylbenzamide (C142A)

(1067) ##STR00491##

(1068) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.67 (1H, d, J=7.8 Hz), 7.43 (1H, d, J=7.3 Hz), 7.33 (1H, t, J=7.6 Hz), 3.40 (6H, bs), 2.43 (3H, s).

Reference Production Example 143

(1069) In the same manner as in Reference Production Example 76, except that a raw material was used in place of an amide compound, production was performed.

3′-bromo-2′-methylacetophenone (C143A)

(1070) ##STR00492##

(1071) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.66 (1H, dd, J=7.9, 1.3 Hz), 7.48 (1H, dd, J=7.8, 0.9 Hz), 7.12 (1H, t, J=7.8 Hz), 2.57 (3H, s), 2.51 (3H, s).

Reference Production Example 144

(1072) In the same manner as in Reference Production Example 140, except that a raw material was used in place of a carboxylic acid compound, production was performed.

2-fluoro-N-methoxy-N-methyl-3-trifluoromethylbenzamide (C144A)

(1073) ##STR00493##

(1074) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.69 (1H, t, J=7.3 Hz), 7.64 (1H, t, J=6.5 Hz), 7.32 (1H, t, J=7.8 Hz), 3.53 (3H, s), 3.39 (3H, s).

Reference Production Example 145

(1075) A mixture of 6.81 g of 3-hydroxyacetophenone, 8.61 g of vinyl acetate, 1.0 g of chloro(1,5-cyclooctadiene)iridium (I) dimer, 6.36 g of sodium carbonate, and 100 mL of toluene was stirred while heating at 100° C. for 3 hours. After cooling to room temperature, the solvent was distilled off and then the residue was subjected to silica gel column chromatography to obtain 1-(3-vinyloxyphenyl)ethanone (C145A).

(1076) ##STR00494##

(1077) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.67 (1H, dq, J=7.7, 0.9 Hz), 7.59 (1H, dd, J=2.3, 1.6 Hz), 7.43 (1H, t, J=7.9 Hz), 7.22 (1H, dq, J=8.2, 1.2 Hz), 6.68 (1H, dd, J=13.7, 6.0 Hz), 4.83 (1H, dd, J=13.7, 1.8 Hz), 4.52 (1H, dd, J=6.0, 1.8 Hz), 2.61 (3H, s).

Reference Production Example 146

(1078) In the same manner as in Reference Production Example 130, except that a raw material was used in place of a phenol compound, production was performed.

4-methoxyindan-1-one (C146A)

(1079) ##STR00495##

(1080) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.36-7.35 (2H, m), 7.06-7.02 (1H, m), 3.91 (3H, s), 3.06-3.03 (2H, m), 2.71-2.68 (2H, m).

Reference Production Example 147

(1081) In the same manner as in Reference Production Example 140, except that a raw material was used in place of a carboxylic acid compound, production was performed.

3-bromo-N-methoxy-2, N-dimethylbenzamide (C147A)

(1082) ##STR00496##

(1083) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.59 (1H, d, J=8.0 Hz), 7.22 (1H, d, J=7.3 Hz), 7.09 (1H, t, J=7.8 Hz), 3.41 (3H, bs), 3.38 (3H, bs), 2.37 (3H, s).

Reference Production Example 148

Step (1)

(1084) To a mixture of 136.2 g of sodium sulfate, 480 mL of water, and 8.6 g of chloral hydrate, a mixture of 6.1 g of 2-fluoro-5-methylaniline, 4.2 mL of concentrated hydrochloric acid, and 24 mL of water was added and, furthermore, a mixture of 10.6 g of hydroxylamine hydrochloride and 30 mL of water was added, under stirring. After stirring while heating under reflux for 1.5 hours, the precipitated solid was collected by filtration to obtain N-(2-fluoro-5-methylphenyl)-2-hydroxyiminoacetamide. To a mixture of 19.5 mL of concentrated sulfuric acid and 4 mL of water, the N-(2-fluoro-5-methylphenyl)-2-hydroxyiminoacetamide was added, followed by stirring at 80° C. for one hour. After cooling, the reaction solution was poured into ice water and the precipitated solid was collected by filtration to obtain 4-methyl-7-fluoroisatin.

(1085) To a mixture of the obtained 4-methyl-7-fluoroisatin, 9.0 g of sodium hydroxide, and 40 mL of water, 3 mL of a 30% hydrogen peroxide solution was added. While maintaining the temperature at 70° C., the 25 pH of the reaction solution was adjusted to 4 by adding dropwise acetic acid. The precipitated solid was collected by filtration to obtain 2.3 q of 2-amino-3-fluoro-6-methylbenzoic acid.

(1086) ##STR00497##

(1087) .sup.1H-NMR (DMSO-D.sub.6) δ(ppm): 7.03 (1H, dd, J=11.3, 8.2 Hz), 6.39 (1H, dd, J=8.2, 5.1 Hz), 2.32 (3H, s).

Step (2)

(1088) To a mixture of 2.3 g of 2-amino-3-fluoro-6-methylbenzoic acid, 70 mL of ethyl acetate, and 70 mL of ethanol, 13.7 mL of a 2.0M diethyl ether solution of trimethylsilyldiazomethane was added under ice cooling. After stirring at room temperature for 1.5 hours, the reaction solution was concentrated under reduced pressure. Water was poured into the obtained residue, followed by extraction with methyl tert-butyl ether. The organic layer was washed in turn with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 0.81 g of 2-amino-3-fluoro-6-methylbenzoic acid methyl ester.

(1089) ##STR00498##

(1090) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 6.94 (1H, dd, J=10.9, 8.2 Hz), 6.45-6.41 (1H, m), 5.26 (2H, br s), 3.91 (3H, s), 2.41 (3H, s).

Step (3)

(1091) To a mixture of 0.81 g of 2-amino-3-fluoro-6-methylbenzoic acid methyl ester and 15 mL of toluene, 2.0 g of triphosgene was added at room temperature, followed by stirring while heating under reflux for 3 hours. After concentration under reduced pressure, 0.92 g of 2-isocyanate-3-fluoro-6-methylbenzoic acid methyl ester was obtained.

(1092) ##STR00499##

(1093) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.09 (1H, t, J=8.7 Hz), 7.02-6.98 (1H, m), 3.96 (3H, s), 2.30 (3H, s).

Step (4)

(1094) Under ice cooling, 0.65 g of anhydrous aluminum chloride was added to 10 mL of N,N-dimethylformamide, followed by stirring for 20 minutes.

(1095) Sodium azide (0.32 g) was added and, after stirring for 15 minutes, 0.92 g of a 2-isocyanate-3-fluoro-6-methylbenzoic acid methyl ester was added and the mixture was heated and stirred at 80° C. for 4 hours.

(1096) After cooling, the reaction solution was added in a mixture of 1.0 g of sodium nitrite and 200 mL of ice water while stirring. The mixture was acidified with 10% hydrochloric acid and then extracted with ethyl acetate. The organic layer was washed in turn with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain 1.4 g of 3-fluoro-6-methyl-2-(5-oxo-4,5-dihydrotetrazol-1-yl)benzoic acid methyl ester.

(1097) ##STR00500##

(1098) .sup.1H-NMR (DMSO-D.sub.6) δ(ppm): 7.65-7.62 (1H, m), 7.59-7.56 (1H, m), 3.71 (3H, s), 2.38 (3H, s).

Step (5)

(1099) To a mixture of 1.4 g of 3-fluoro-6-methyl-2-(5-oxo-4,5-dihydrotetrazol-1-yl)benzoic acid methyl ester, and 20 mL of N,N-dimethylformamide, 1.2 g of potassium carbonate and 1.3 g of methyl iodide were added at room temperature, followed by stirring for 4 hours. Water was poured into the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed in turn with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 0.65 g of 3-fluoro-6-methyl-2-(4-methyl-5-oxo-4,5-dihydrotetrazol-1-yl)benzoic acid methyl ester.

(1100) ##STR00501##

(1101) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.38 (1H, dd, J=8.6, 5.0 Hz), 7.28 (1H, t, J=8.6 Hz), 3.80 (3H, s), 3.71 (3H, s), 2.45 (3H, s).

Step (6)

(1102) Under ice cooling, to a mixture of 0.65 g of 3-fluoro-6-methyl-2-(4-methyl-5-oxo-4,5-dihydrotetrazol-1-yl)benzoic acid methyl ester and 11 mL of tetrahydrofuran, 5.4 mL of a 1.0M tetrahydrofuran solution of lithium triethylborohydride was added at room temperature, followed by stirring for one hour. Water was poured into the reaction solution, and the solution was acidified with 10% hydrochloric acid and then extracted with ethyl acetate. The organic layer was washed in turn with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain 0.58 g of 1-(2-hydroxymethyl-3-methyl-6-fluorophenyl)-4-methyl-1,4-dihydrotetrazol-5-one.

(1103) ##STR00502##

(1104) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.37 (1H, dd, J=8.6, 5.4 Hz), 7.15 (1H, t, J=8.6 Hz), 4.54-4.36 (2H, m), 3.76 (3H, s), 3.28-3.24 (1H, m), 2.50 (3H, s).

Step (7)

(1105) To a mixture of 0.58 g of 1-(2-hydroxymethyl-3-methyl-6-fluorophenyl)-4-methyl-1,4-dihydrotetrazol-5-one and 8 mL of chloroform, 1.32 g of phosphorus tribromide was added, followed by stirring at room temperature for 20 hours. Ice water was poured into the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed in turn with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 0.66 g of 1-(2-bromomethyl-3-methyl-6-fluorophenyl)-4-methyl-, 4-dihydrotetrazol-5-one (C148A).

(1106) ##STR00503##

(1107) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.36 (1H, dd, J=8.7, 5.6 Hz), 7.16 (1H, t, J=8.7 Hz), 4.43 (1H, d, J=10.6 Hz), 4.32 (1H, d, J=10.6 Hz), 3.76 (3H, s), 2.46 (3H, s).

Reference Production Example 149

Step (1)

(1108) To a mixture of 272.4 g of sodium sulfate, 960 mL of water, and 17.2 g of chloral hydrate, a mixture of 12.2 g of 4-fluoro-3-methylaniline, 8.4 mL of concentrated hydrochloric acid, and 48 mL of water was added. Under stirring, a mixture of 21.1 g of hydroxylamine hydrochloride and 60 mL of water was further added.

(1109) After stirring while heating under reflux for 40 minutes, the precipitated solid was collected by filtration to obtain 25.4 g of N-(4-fluoro-3-methylphenyl)-2-hydroxyiminoacetamide.

(1110) To a mixture of 78 mL of concentrated sulfuric acid and 16 mL of water, 25.4 g of N-(4-fluoro-3-methylphenyl)-2-hydroxyiminoacetamide was added.

(1111) After stirring at 80° C. for one hour, the reaction solution was poured into 500 mL of ice water and the precipitated solid was collected by filtration to obtain a mixture of 4-methyl-5-fluoroisatin with 6-methyl-5-fluoroisatin.

(1112) The obtained mixture of 4-methyl-5-fluoroisatin with 6-methyl-5-fluoroisatin is mixed with a mixture of 18.0 g of sodium hydroxide and 80 mL of water, and then 6 mL of 30% hydrogen peroxide solution was added. While maintaining the temperature at 70° C., the pH of the reaction solution was adjusted to 4 by adding dropwise acetic acid. The precipitated solid was collected by filtration to obtain 11.5 g of a mixture of 6-amino-3-fluoro-2-methylbenzoic acid and 2-amino-5-fluoro-4-methylbenzoic acid.

(1113) To a mixture of 11.5 g of the mixture of 6-amino-3-fluoro-2-methylbenzoic acid and 2-amino-5-fluoro-4-methylbenzoic acid, 340 mL of ethyl acetate, and 340 mL ethanol, 68 mL of a 2.0M diethyl ether solution of trimethylsilyldiazomethane was added under ice cooling. After stirring at room temperature for 1.5 hours, the solution was concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 3.0 g of 6-amino-3-fluoro-2-methylbenzoic acid methyl ester.

(1114) ##STR00504##

(1115) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 6.93 (1H, t, J=9.0 Hz), 6.48 (1H, dd, J=9.0, 4.5 Hz), 4.82 (2H, br s), 3.91 (3H, s), 2.31 (3H, d, J=2.7 Hz).

Step (2)

(1116) To a mixture of 3.0 g of 6-amino-3-fluoro-2-methylbenzoic acid methyl ester and 60 mL of toluene, 7.6 g of triphosgene was added at room temperature, followed by stirring while heating under reflux for 3 hours. After concentration under reduced pressure, 3.6 g of 6-isocyanate-3-fluoro-2-methylbenzoic acid methyl ester was obtained.

(1117) ##STR00505##

(1118) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.04 (1H, t, J=8.8 Hz), 6.94 (1H, dd, J=8.8, 4.6 Hz), 3.98 (3H, s), 2.26 (3H, d, J=2.5 Hz).

Step (3)

(1119) Under ice cooling, 2.5 g of anhydrous aluminum chloride was added to 30 mL of N,N-dimethylformamide, followed by stirring for 20 minutes. Sodium azide (1.2 g) was added and, after stirring for 15 minutes, 3.6 g of 6-isocyanate-3-fluoro-2-methylbenzoic acid methyl ester was added, followed by heating and stirring at 80° C. for 4 hours. After cooling, the reaction solution was added in a mixture of 4.0 g of sodium nitrite and 500 mL of ice water while stirring. The mixture was acidified with 10% hydrochloric acid and then extracted with ethyl acetate. The organic layer was washed in turn with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain 6.0 g of 2-methyl-3-fluoro-6-(5-oxo-4,5-dihydrotetrazol-1-yl)benzoic acid methyl ester.

(1120) ##STR00506##

(1121) .sup.1H-NMR (DMSO-D.sub.6) δ(ppm): 7.62-7.56 (2H, m), 5.29 (1H, br s), 3.73 (3H, s), 2.29 (3H, d, J=2.3 Hz).

Step (4)

(1122) To a mixture of 6.0 g of 2-methyl-3-fluoro-6-(5-oxo-4,5-dihydrotetrazol-1-yl)benzoic acid methyl ester and 85 mL of N,N-dimethylformamide, 4.7 g of potassium carbonate and 4.9 g of methyl iodide were added at room temperature, followed by stirring for 6 hours. Water was poured into the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed in turn with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 2.8 g of 2-methyl-3-fluoro-6-(4-methyl-5-oxo-4,5-dihydrotetrazol-1-yl)benzoic acid methyl ester.

(1123) ##STR00507##

(1124) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.47 (1H, dd, J=8.9, 4.6 Hz), 7.25 (1H, t, J 25=8.9 Hz), 3.84 (3H, s), 3.69 (3H, s), 2.36 (3H, d, J=2.4 Hz).

Step (5)

(1125) Under ice cooling, to a mixture of 2.8 g of 2-methyl-3-fluoro-6-(4-methyl-5-oxo-4,5-dihydrotetrazol-1-yl)benzoic acid methyl ester and 46 mL of tetrahydrofuran, 22.9 mL of a 1.0M tetrahydrofuran solution of lithium triethylborohydride was added at room temperature, followed by stirring for one hour. Water was poured into the reaction solution, and the solution was acidified with 10% hydrochloric acid and then extracted with ethyl acetate. The organic layer was washed in turn with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain 2.4 g of 1-(2-hydroxymethyl-3-methyl-4-fluorophenyl)-4-methyl-1,4-dihydrotetrazol-5-one.

(1126) ##STR00508##

(1127) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.21 (1H, dd, J=8.7, 5.1 Hz), 7.15 (1H, t, J 15=8.7 Hz), 4.47 (2H, dd, J=7.2, 1.0 Hz), 3.75 (3H, s), 2.45 (3H, d, J=2.4 Hz).

Step (6)

(1128) To a mixture of 2.4 g of 1-(2-hydroxymethyl-3-methyl-4-fluorophenyl)-4-methyl-1,4-dihydrotetrazol-5-one and 34 mL of chloroform, 5.5 g of phosphorus tribromide was added, followed by stirring at room temperature for 20 hours. Ice water was poured into the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed in turn with water and a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to obtain 2.5 g of 1-(2-bromomethyl-3-methyl-4-fluorophenyl)-4-methyl-1,4-dihydrotetrazol-5-one (C149A).

(1129) ##STR00509##

(1130) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.22 (1H, dd, J=8.7, 5.1 Hz), 7.16 (1H, t, J=8.7 Hz), 4.46 (2H, s), 3.75 (3H, s), 2.39 (3H, d, J=2.4 Hz).

Reference Production Example 150

(1131) To a mixture of 15.6 g of sodium tetrahydroborate and 200 ml of tetrahydrofuran, 50 g of 2-methyl-6-nitrobenzoic acid was added at room temperature. To the reaction mixture, 34 ml of dimethylsulfuric acid was added at 0° C., followed by stirring at room temperature for 20 hours. 5% Hydrochloric acid (300 ml) was added at 0° C., followed by stirring for one hour. After extraction with ethyl acetate, the organic layer was washed with water, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain 30.5 g of 2-methyl-6-nitrobenzyl alcohol (C150A).

(1132) ##STR00510##

(1133) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.71 (1H, d, J=7.7 Hz), 7.49 (1H, d, J=7.5 Hz), 7.36 (1H, t, J=7.9 Hz), 4.71 (2H, d, J=7.2 Hz), 2.62 (1H, t, J=7.4 Hz), 2.56 (3H, s).

Reference Production Example 151

(1134) To a mixture of 30.5 g of C150A and 100 ml of chloroform, 74.1 g of phosphorus tribromide was added at room temperature, followed by stirring for 10 hours. Ice water (200 ml) was added and the solution was extracted with chloroform. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain 35 g of 2-methyl-6-nitrobenzyl bromide (C151A).

(1135) ##STR00511##

(1136) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.75 (1H, d, J=8.2 Hz), 7.46 (1H, d, J=7.7 Hz), 7.36 (1H, t, J=7.8 Hz), 4.72 (2H, s), 2.54 (3H, s).

Reference Production Example 152

(1137) C153A (1.90 g) was heated and stirred at 220° C. for 36 hours. The obtained oily substance was subjected to silica gel column chromatography to obtain 0.43 g of 1-(2,2-dimethyl-2,3-dihydrobenzofuran-4-yl)ethanone (C152A).

(1138) ##STR00512##

(1139) .sup.1H-NMR (CDCl.sub.3) δ: 7.37 (1H, d, J=7.9 Hz), 7.22 (1H, t, J=7.8 Hz), 6.92 (1H, d, J=7.9 Hz), 3.36 (2H, s), 2.59 (3H, s), 1.47 (6H, s).

Reference Production Example 153

(1140) A mixture of 20.4 g of 3-hydroxyacetophenone, 90.6 g of 3-chloro-2-methyl-1-propene, 24.9 g of potassium carbonate, and 150 mL of acetonitrile was stirred while heating under reflux for 17 hours. After cooling to room temperature, the reaction mixture was filtered to obtain 28.4 g of a crude 1-[3-(2-methylallyloxyl)phenyl]ethanone (C153A).

(1141) ##STR00513##

(1142) .sup.1H-NMR (CDCl.sub.3) δ: 7.54 (1H, dd, J=7.6, 0.7 Hz), 7.51 (1H, s), 7.37 (1H, t, J=7.9 Hz), 7.14 (1H, dd, J=8.2, 2.7 Hz), 5.12 (1H, s), 5.01 (1H, s), 4.49 (2H, s), 2.60 (3H, s), 1.84 (3H, s).

Reference Production Example 154

(1143) In the same manner as in Reference Production Example 96, except that a raw material was used in place of a carboxylic acid compound, production was performed.

(1144) ##STR00514##

(1145) .sup.1H-NMR (CDCl.sub.3) δ: 7.01 (1H, dd, J=7.3, 1.8 Hz), 6.90-6.84 (2H, m), 6.02 (2H, s), 3.63 (3H, s), 3.35 (3H, s).

Reference Production Examples 201 to 204

(1146) In the same manner as in Reference Production Example 140, except that each raw material was used in place of a ketone compound, production was performed.

1-cyclohexylethanone oxime (C201A)

(1147) ##STR00515##

(1148) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 9.18 (1H, bs), 2.18-2.10 (1H, m), 1.86 (3H, s), 1.83-1.77 (4H, m), 1.71-1.66 (1H, m), 1.33-1.15 (5H, m).

1-cyclohexan-1-enylethanone oxime (C202A)

(1149) ##STR00516##

(1150) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.98 (1H, bs), 6.21-6.18 (1H, m), 2.29-2.25 (2H, m), 2.21-2.16 (2H, m), 2.02 (3H, s), 1.69-1.58 (4H, m).

3-methylpent-3-en-2-one oxime (C203A)

(1151) ##STR00517##

(1152) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 6.04-5.97 (1H, m), 2.03 (3H, s), 1.84 (3H, s), 1.79 (3H, d, J=7.0 Hz).

5-methylhex-3-en-2-one oxime (C204A)

(1153) ##STR00518##

(1154) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.36 (1H, bs), 6.10-6.00 (2H, m), 2.48-2.37 (1H, m), 1.99 (3H, s), 1.05 (6H, d, J=6.6 Hz).

Reference Production Example 205

(1155) In the same manner as in Reference Production Example 19, except that a raw material was used in place of a ketone compound, production was performed.

1-[l-(3-trifluoromethylphenyl)cyclopropyl]ethanone oxime (C205A)

(1156) ##STR00519##

(1157) .sup.1H-NMR (CDCl.sub.3) δ: 7.52-7.40 (5H, m), 1.80 (3H, s), 1.31 (2H, dd, J=6.7, 4.6 Hz), 1.08 (2H, dd, J=6.7, 4.6 Hz).

Reference Production Example 206

(1158) In the same manner as in Reference Production Example 140, except that a raw material was used in place of an amide compound, production was performed.

1-[l-(3-trifluoromethylphenyl)cyclopropyl]ethanone (C206A)

(1159) ##STR00520##

(1160) .sup.1H-NMR (CDCl.sub.3) δ: 7.62 (1H, s), 7.58-7.47 (3H, m), 2.00 (3H, s), 1.67 (2H, dd, J=7.0, 3.9 Hz), 1.21 (2H, dd, J=6.9, 4.0 Hz).

Reference Production Example 207

(1161) In the same manner as in Reference Production Example 96, except that a raw material was used in place of a carboxylic acid compound, production was performed.

N-methoxy-N-methyl-1-(3-trifluoromethylphenyl)cyclopropanecarboxylic acid amide (C207A)

(1162) ##STR00521##

(1163) .sup.1H-NMR (CDCl.sub.3) δ: 7.52-7.47 (3H, m), 7.44-7.40 (1H, m), 3.14 (3H, s), 3.13 (3H, s), 1.50 (2H, dd, J=7.0, 4.7 Hz), 1.15 (2H, dd, J=7.0, 4.7 Hz).

Reference Production Example 208

(1164) To a mixture of 17.2 g of 3-pentanone, 20.6 g of tert-butyl nitrite, and 240 mL of methanol, 77.2 mL of a 28% sodium methoxide-methanol solution was added dropwise under ice cooling. After stirring at 0° C. for 4 hours, the temperature was raised to room temperature while stirring over 4 hours. The pH of the reaction mixture was adjusted to 7 by adding 1N hydrochloric acid and the mixture was extracted with chloroform. The organic layer was washed with a saturated saline solution, dried over anhydrous magnesiumsulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 8.20 g of pentane-2,3-dione-2-oxime (C208A).

(1165) ##STR00522##

(1166) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.48 (1H, s), 2.80 (2H, q, J=7.4 Hz), 1.99 (3H, s), 1.10 (3H, t, J=7.3 Hz).

Reference Production Example 209

(1167) To a mixture of 8.20 g of C208A, 19.6 g of potassium carbonate, and 140 mL of acetonitrile, 10.1 g of iodomethane was added dropwise under ice cooling, followed by stirring at room temperature for 2 hours. Water was added to the reaction mixture, followed by extraction with chloroform. The organic layer was washed with a saturated saline solution, dried over anhydrous magnesiumsulfate, and then concentrated under reduced pressure to obtain 9.04 g of pentane-2,3-dione-2-(O-methyloxime) (C209A).

(1168) ##STR00523##

(1169) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 4.04 (3H, s), 2.81 (2H, q, J=7.3 Hz), 1.91 (3H, s), 1.09 (3H, t, J=7.3 Hz).

Reference Production Example 210

(1170) To a mixture of 9.04 g of C209A, 7.22 g of tert-butyl nitrite, and 84 mL of methanol, 27.0 mL of a 28% sodium methoxide-methanol solution was added dropwise under ice cooling, followed by stirring at room temperature for 8 hours. The pH of the reaction mixture was adjusted to 7 by adding 1N hydrochloric acid, followed by extraction with chloroform. The organic layer was washed with a saturated saline solution, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to obtain 3.37 g of pentane-2,3,4-trione-2-(O-methyloxime)-4-oxime (C210A).

(1171) ##STR00524##

(1172) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 9.96 (1H, bs), 4.07 (3H, s), 2.11 (3H, s), 2.05 (3H, s).

Reference Production Example 211

(1173) To a mixture of 3.16 g of C210A, 1.67 g of O-methylhydroxyamine hydrochloride and 40 mL of ethanol, 1.0 mL of hydrochloric acid was added, followed by stirring at room temperature for 2 hours. To the reaction mixture, an aqueous saturated sodium hydrogen carbonate solution was added, followed by extraction with chloroform. The organic layer was washed with a saturated saline solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure.

(1174) The obtained residue was subjected to silica gel chromatography to obtain 1.23 g of one isomer (C211A) of pentane-2,3,4-trione-2,3-bis-(O-methyloxime)-4-oxime and 0.96 g of the other one isomer (C211B).

(1175) ##STR00525##
C211A:

(1176) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 9.03 (1H, br s), 3.98 (3H, s), 3.95 (3H, s), 2.11 (3H, s), 1.97 (3H, s).

(1177) C211B:

(1178) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.98 (1H, s), 3.97 (3H, s), 3.94 (3H, s), 2.04 (3H, s), 2.01 (3H, s).

Reference Production Examples 214 to 216

(1179) In the same manner as in Reference Production Example 19, except that each raw material was used in place of a ketoned compound, production was performed.

1-(2-phenylcyclopropyl)ethanone oxime (C214A)

(1180) ##STR00526##

(1181) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.45 (1.0H, bs), 7.30-7.26 (2.0H, m), 7.21-7.09 (3.0H, m), 2.76-2.71 (0.2H, m), 2.31-2.26 (0.2H, m), 2.22-2.17 (0.8H, m), 1.86 (2.2H, s), 1.85-1.80 (0.8H, m), 1.70 (0.8H, s), 1.44-1.17 (2.0H, m).

1-[2-(4-chlorophenyl)cyclopropyl]ethanone oxime (C215A)

(1182) ##STR00527##

(1183) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.25-7.22 (2H, m), 7.04-7.01 (2H, m), 2.19-2.14 (1H, m), 1.85 (3H, s), 1.81-1.76 (1H, m), 1.44-1.39 (1H, m), 1.19-1.14 (1H, m).

(1184) ##STR00528##

1-[2-(2,6-dichlorophenyl)cyclopropyl]ethanone oxime (C216A)

(1185) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.29 (2H, d, J=7.9 Hz), 7.12 (1H, t, J=8.0 Hz), 2.77-2.71 (1H, m), 2.28-2.22 (1H, m), 1.74 (3H, s), 1.57-1.47 (2H, m).

Reference Production Examples 220 to 222

(1186) In the same manner as in Reference Production Example 76, except that each raw material was used in place of an amide compound, production was performed.

1-(2-phenylcyclopropyl)ethanone (C220A)

(1187) ##STR00529##

(1188) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.31-7.27 (2H, m), 7.23-7.19 (1H, m), 7.11-7.09 (2H, m), 2.55-2.50 (1H, m), 2.31 (3H, s), 2.24-2.20 (1H, m), 1.70-1.65 (1H, m), 1.41-1.36 (1H, m). 1-[2-(4-chlorophenyl)cyclopropyl]ethanone (C221A)

(1189) ##STR00530##

(1190) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.26-7.23 (2H, m), 7.04-7.00 (2H, m), 2.52-2.47 (1H, m), 2.31 (3H, s), 2.20-2.16 (1H, m), 1.69-1.64 (1H, m), 1.36-1.32 (1H, m).

1-[2-(2,6-dichlorophenyl)cyclopropyl]ethanone (C222A)

(1191) ##STR00531##

(1192) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.29 (2H, d, J=7.8 Hz), 7.13 (1H, dd, J=8.5, 7.8 Hz), 2.42 (3H, s), 2.40-2.36 (1H, m), 2.27-2.23 (1H, m), 1.85-1.80 (1H, m), 1.46-1.41 (1H, m).

Reference Production Example 223

(1193) In the same manner as in Reference Production Example 99, except that a raw material was used in place of a halogenated acyl compound, production was performed.

3-phenyl-N-methoxy-N-methylacrylamide (C223A)

(1194) ##STR00532##

(1195) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.74 (1H, d, J=15.8 Hz), 7.59-7.57 (2H, m), 7.42-7.36 (3H, m), 7.04 (1H, d, J=15.8 Hz), 3.77 (3H, s), 3.32 (3H, s).

Reference Production Examples 224 to 225

(1196) In the same manner as in Reference Production Example 140, except that a raw material was used in place of a carboxylic acid compound, production was performed.

3-(4-chlorophenyl)-N-methoxy-N-methylacrylamide (C224A)

(1197) ##STR00533##

(1198) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.68 (1H, d, J=15.8 Hz), 7.52-7.49 (2H, m), 7.37-7.34 (2H, m), 7.01 (1H, d, J=15.8 Hz), 3.77 (3H, s), 3.32 (3H, s).

3-(2,6-dichlorophenyl)-N-methoxy-N-methylacrylamide (C225A)

(1199) ##STR00534##

(1200) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.79 (1H, d, J=16.3 Hz), 7.36 (2H, d, J=8.0 Hz), 7.20-7.14 (2H, m), 3.76 (3H, s), 3.33 (3H, s).

Reference Production Example 226

(1201) A mixture of 2.93 g of C223A, 6.60 g of trimethylsulfoxonium iodide, 0.72 g of sodium borohydride, and 30 mL of dimethylformamide was stirred at 0° C. for 6 hours. After completion of the reaction, an aqueous saturated ammonium chloride solution was added, followed by stirring and further extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated to obtain a crude product. The obtained crude product was subjected to silica gel column chromatography to obtain N-methoxy-N-methyl-2-phenylcyclopropanecarboxylic acid amide (C226A).

(1202) ##STR00535##

(1203) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.31-7.27 (2H, m), 7.20 (1H, tt, J=7.4, 1.6 Hz), 7.15-7.13 (2H, m), 3.70 (3H, s), 3.24 (3H, s), 2.53-2.48 (1H, m), 2.42 (1H, bs), 1.66-1.61 (1H, m), 1.34-1.29 (1H, m).

Reference Production Examples 227 to 228

(1204) In the same manner as in Reference Production Example 226, except that each raw material was used in place of an amide compound, production was performed.

N-methoxy-N-methyl-2-(4-chlorophenyl)cyclopropanecarboxylic acid amide (C227A)

(1205) ##STR00536##

(1206) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.26-7.23 (2H, m), 7.08-7.04 (2H, m), 3.69 (3H, s), 3.24 (3H, s), 2.49-2.45 (1H, m), 2.37 (1H, bs), 1.66-1.61 (1H, m), 1.30-1.25 (1H, m).

N-methoxy-N-methyl-2-(2,6-dichlorophenyl)cyclopropanecarboxylic acid amide (C228A)

(1207) ##STR00537##

(1208) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.28 (2H, d, J=8.0 Hz), 7.12 (1H, t, J=8.0 Hz), 3.79 (3H, s), 3.28 (3H, s), 2.54-2.49 (2H, m), 1.72-1.67 (1H, m), 1.47-1.42 (1H, m).

Reference Production Examples 251 to 259

(1209) In the same manner as in Reference Production Example 19, except that each raw material was used in place of a katone compound, production was performed.

1-pyridin-3-ylethanone oxime (C251A)

(1210) ##STR00538##

(1211) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.93 (1H, d, J=2.1 Hz), 8.78 (1H, s), 8.61 (1H, dd, J=4.8, 1.6 Hz), 7.96 (1H, dt, J=8.0, 2.0 Hz), 7.33 (1H, dd, J=8.0, 4.8 Hz), 2.31 (3H, s).

1-pyridin-2-ylethanone oxime (C252A)

(1212) ##STR00539##

(1213) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.63 (1H, dq, J=4.8, 0.8 Hz), 7.84 (1H, dt, J=8.1, 1.1 Hz), 7.69 (1H, td, J=7.7, 1.9 Hz), 7.28 (1H, ddd, J=7.5, 4.8, 1.1 Hz), 2.40 (3H, s).

1-(6-trifluoromethylpyridin-2-yl)ethanone oxime (C253A)

(1214) ##STR00540##

(1215) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.09 (1H, d, J=7.8 Hz), 7.84 (1H, t, J=7.8 Hz), 7.64 (1H, d, J=7.8 Hz), 2.40 (3H, s).

1-(1-methyl-1H-pyrrol-3-yl)ethanone oxime (C254A)

(1216) ##STR00541##

(1217) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.62 (0.5H, t, J=1.8 Hz), 6.86 (0.5H, t, J=1.9 Hz), 6.59 (0.5H, t, J=2.5 Hz), 6.57 (0.5H, t, J=2.5 Hz), 6.48 (0.5H, dd, J=2.66, 1.69 Hz), 6.40 (0.5H, dd, J=2.8, 1.8 Hz), 3.69 (1.5H, s), 3.65 (1.5H, s), 2.19 (1.5H, s), 2.18 (1.5H, s).

1-(1-methyl-1H-pyrrol-2-yl)ethanone oxime (C255A)

(1218) ##STR00542##

(1219) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.64 (1H, bs), 6.66 (1H, t, J=2.2 Hz), 6.44 (1H, dd, J=3.9, 1.8 Hz), 6.12 (1H, dd, J=3.9, 2.8 Hz), 3.80 (3H, s), 2.23 (3H, s).

1-(4-methyl-2-thienyl)ethanone oxime (C256A)

(1220) ##STR00543##

(1221) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.41 (1H, bs), 7.06 (1H, s), 6.86 (1H, s), 2.28 (3H, s), 2.25 (3H, s).

1-(2-thienyl)ethanone oxime (C257A)

(1222) ##STR00544##

(1223) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.63 (1H, bs), 7.58 (0.2H, dd, J=5.1, 1.0 Hz), 7.52 (0.2H, dd, J=3.7, 1.1 Hz), 7.29 (0.8H, dd, J=5.1, 1.0 Hz), 7.26 (0.8H, dd, J=3.7, 1.1 Hz), 7.12 (0.2H, dd, J=5.1, 3.8 Hz), 7.04 (0.8H, dd, J=5.1, 3.8 Hz), 2.39 (0.7H, s), 2.32 (2.3H, s). 1-(3-methyl-2-thienyl)ethanone oxime (C258A)

(1224) ##STR00545##

(1225) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.52 (1H, bs), 7.19 (1H, d, J=5.4 Hz), 6.86 (1H, d, J=5.4 Hz), 2.39 (3H, s), 2.32 (3H, s). 1-(2-furyl)ethanone oxime (C259A)

(1226) ##STR00546##

(1227) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 9.00 (1H, bs), 7.47 (1H, dd, J=1.8, 0.8 Hz), 6.64 (1H, dd, J=3.4, 0.8 Hz), 6.44 (1H, dd, J=3.4, 1.8 Hz), 2.22 (3H, s).

Reference Production Example 260

(1228) A mixture of 2.14 g of C265A, 1.12 g of potassium hydroxide, and 40 mL of ethanol was stirred while heating under reflux for 2 hours. After completion of the reaction, water and 1N hydrochloric acid were added, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated to obtain a crude product. The obtained crude product was subjected to silica gel column chromatography to obtain 1-(6-fluorobenzo[d]isoxazol-3-yl)ethanone oxime (C260A).

(1229) ##STR00547##

(1230) .sup.1H-NMR (DMSO-D.sub.6) δ(ppm): 12.31 (1H, s), 8.10 (1H, dd, J=8.8, 5.7 Hz), 7.78 (1H, dd, J=9.0, 1.9 Hz), 7.36 (1H, td, J=9.1, 2.2 Hz), 2.28 (3H, s).

Reference Production Examples 261 to 263

(1231) In the same manner as in Reference Production Example 19, except that each raw material was used in place of a ketone compound, production was performed.

1-(1,5-dimethyl-1H-pyrazol-3-yl)ethanone oxime (C261A)

(1232) ##STR00548##

(1233) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 6.30 (1H, s), 3.79 (3H, s), 2.28 (3H, d, J=3.2 Hz), 2.27 (3H, s).

4-(3-thienyl)butan-3-en-2-one oxime (C262A)

(1234) ##STR00549##

(1235) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.33-7.28 (3H, m), 6.91 (1H, d, J=16.5 Hz), 6.67 (1H, d, J=16.3 Hz), 2.10 (3H, s).

1-[2-(3-thienyl)cyclopropyl]ethanone oxime (C263A)

(1236) ##STR00550##

(1237) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.64 (1.0H, s), 7.26-7.23 (1.0H, m), 6.99-6.97 (0.2H, m), 6.93-6.92 (0.8H, m), 6.90 (0.2H, dd, J=4.9, 1.0 Hz), 6.85 (0.8H, dd, J=5.0, 1.1 Hz), 2.72-2.68 (0.2H, m), 2.35-2.30 (0.2H, m), 2.27-2.22 (0.8H, m), 1.84 (2.2H, s), 1.82-1.77 (0.8H, m), 1.67 (0.8H, s), 1.39-1.32 (1.0H, m), 1.28-1.22 (0.2H, m), 1.16-1.11 (0.8H, m).

Reference Production 264

(1238) To a mixture of 5.0 g of 2-bromo-6-trifluoromethylpyridine, 3.1 mL of dimethylaceto, and amide diethyl ether, butyllithium (n-BuLi) was added dropwise at −78° C., followed by stirring for 6 hours. After completion of the reaction, water was added, followed by stirring and further extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated to obtain a crude product. The obtained crude product was subjected to silica gel column chromatography to obtain 1-(6-trifluoromethylpyridin-2-yl)ethanone (C264A).

(1239) ##STR00551##

(1240) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.22 (1H, d, J=7.8 Hz), 8.04 (1H, t, J=7.8 Hz), 7.86 (1H, d, J=7.8 Hz), 2.77 (3H, s).

Reference Production Example 265

(1241) In the same manner as in Reference Production Example 19, except that a raw material was used in place of a ketone compound, production was performed.

1-(2,4-difluorophenyl)propane-1,2-diondioxime (C265A)

(1242) ##STR00552##

(1243) .sup.1H-NMR (DMSO-D.sub.6) δ(ppm): 11.87 (0.3H, s), 11.82 (0.7H, s), 11.58 (0.7H, s), 11.32 (0.3H, s), 7.54-7.47 (0.3H, m), 7.30-7.19 (1.7H, m), 7.14-7.05 (1.0H, m), 2.08 (0.9H, s), 2.06 (2.1H, s).

Reference Production Examples 266 to 268

(1244) In the same manner as in Reference Production Example 76, except that each raw material was used in place of an amide compound, production was performed.

1-(1,5-dimethyl-1H-pyrazol-3-yl)ethanone (C266A)

(1245) ##STR00553##

(1246) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 6.53 (1H, d, J=0.7 Hz), 3.84 (3H, s), 2.54 (3H, s), 2.30 (3H, d, J=0.7 Hz).

4-(3-thienyl)butan-3-en-2-one (C267A)

(1247) ##STR00554##

(1248) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.55-7.54 (1H, m), 7.52 (1H, d, J=16.3 Hz), 7.37-7.35 (1H, m), 7.32-7.31 (1H, m), 6.55 (1H, d, J=16.3 Hz), 2.36 (3H, s).

1-[2-(3-thienyl)cyclopropyl]ethanone (C268A)

(1249) ##STR00555##

(1250) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.27-7.25 (1H, m), 6.96-6.95 (1H, m), 6.84 (1H, d, J=5.0 Hz), 2.59-2.54 (1H, m), 2.31 (3H, s), 2.21-2.17 (1H, m), 1.66-1.61 (1H, m), 1.35-1.30 (1H, m).

Reference Production Example 269

(1251) A mixture of 14 mL of 1-(2,4-difluorophenyl)propan-1-one, 16 mL of amyl nitrite, 10 mL of concentrated hydrochloric acid, and 200 mL of tetrahydrofuran was stirred at room temperature for 6 hours. After completion of the reaction, water was added, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated to obtain a crude product. The obtained crude product was subjected to silica gel column chromatography to obtain 1-(2,4-difluorophenyl)propane-1,2-dione-2-oxime (C269A).

(1252) ##STR00556##

(1253) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 8.16 (1H, s), 7.56-7.50 (1H, m), 6.97-6.92 (1H, m), 6.88-6.82 (1H, m), 2.14 (3H, s).

Reference Production Example 270

(1254) In the same manner as in Reference Production Example 140, except that a raw material was used in place of a carboxylic acid compound, production was performed.

N-methoxy-N-methyl-1,5-dimethyl-1H-pyrazole-3-carboxylic acid amide (C270A)

(1255) ##STR00557##

(1256) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 6.51 (1H, s), 3.84 (3H, s), 3.75 (3H, s), 3.42 (3H, s), 2.30 (3H, s).

N-methoxy-N-methyl-3-(3-thienyl)acrylamide (C271A)

(1257) ##STR00558##

(1258) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.72 (1H, d, J=15.7 Hz), 7.51-7.50 (1H, m), 7.36-7.32 (2H, m), 6.86 (1H, d, J=15.7 Hz), 3.76 (3H, s), 3.31 (3H, s).

Reference Production Example 272

(1259) In the same manner as in Reference Production Example 226, except that a raw material was used in place of an amide compound, production was performed.

N-methoxy-N-methyl-2-(3-thienyl)cyclopropanecarboxylic acid amide (C272A)

(1260) ##STR00559##

(1261) .sup.1H-NMR (CDCl.sub.3) δ(ppm): 7.25 (1H, dd, J=4.8, 3.0 Hz), 6.97 (1H, d, J=2.3 Hz), 6.88 (1H, dd, J=5.0, 0.9 Hz), 3.71 (3H, s), 3.24 (3H, s), 2.55-2.51 (1H, m), 2.37 (1H, bs), 1.61-1.57 (1H, m), 1.28-1.23 (1H, m).

(1262) According to the above method, compounds EP1A-001 to EP12G-513 can be obtained.

(1263) The compounds EP1A-001 to EP12G-513 are as follows:

(1264) ##STR00560## ##STR00561## ##STR00562## ##STR00563## ##STR00564## ##STR00565## ##STR00566## ##STR00567## ##STR00568## ##STR00569## ##STR00570## ##STR00571## ##STR00572## ##STR00573##
wherein Q is a compound represented by the substituent corresponding to each of the following substituent numbers 1 to 513: [substituent number; Q], [1; phenyl group], [2; 2-fluorophenyl group], [3; 3-fluorophenyl group], [4; 4-fluorophenyl group], [5; 2,3-difluorophenyl group], [6; 2,4-difluorophenyl group], [7; 2,5-difluorophenyl group], [8; 2,6-difluorophenyl group], [9; 3,4-difluorophenyl group], [10; 3,5-difluorophenyl group], [11; 2,3,4-trifluorophenyl group], [12; 2,3,5-trifluorophenyl group], [13; 2,4,5-trifluorophenyl group], [14; 2,3,6-trifluorophenyl group], [15; 2,4,6-trifluorophenyl group], [16; 3,4,5-trifluorophenyl group], [17; 3-chlorophenyl group], [18; 4-chlorophenyl group], [19; 3,4-dichlorophenyl group], [20; 3,5-dichlorophenyl group], [21; 3,4,5-trichlorophenyl group], [22; 3-bromophenyl group], [23; 4-bromophenyl group], [24; 3,4-dibromophenyl group], [25; 3,5-dibromophenyl group], [26; 3,4,5-tribromophenyl group], [27; 3-iodophenyl group], [28; 4-iodophenyl group], [29; 3,4-diiodophenyl group], [30; 3,5-diiodophenyl group], [31; 3,4,5-triiodophenyl group], [32; 2-fluoro-3-chlorophenyl group], [33; 2-fluoro-3-bromophenyl group], [34; 2-fluoro-3-iodophenyl group], [35; 2-fluoro-4-chlorophenyl group], [36; 2-fluoro-4-bromophenyl group], [37; 2-fluoro-4-iodophenyl group], [38; 2-fluoro-5-chlorophenyl group], [39; 2-fluoro-5-bromophenyl group], [40; 2-fluoro-5-iodophenyl group], [41; 2-fluoro-6-chlorophenyl group], [42; 2-fluoro-6-bromophenyl group], [43; 2-fluoro-6-iodophenyl group], [44; 3-fluoro-4-chlorophenyl group], [45; 3-fluoro-4-bromophenyl group], [46; 3-fluoro-4-iodophenyl group], [47; 3-fluoro-5-chlorophenyl group], [48; 3-fluoro-5-bromophenyl group], [49; 3-fluoro-5-iodophenyl group], [50; 3-chloro-4-fluorophenyl group], [51; 3-chloro-4-bromophenyl group], [52; 3-chloro-4-iodophenyl group], [53; 3-chloro-5-bromophenyl group], [54; 3-chloro-5-iodophenyl group], [55; 3-iodo-4-fluorophenyl group], [56; 3-iodo-4-chlorophenyl group], [57; 3-iodo-4-bromophenyl group], [58; 3-chloro-4,5-difluorophenyl group], [59; 3-bromo-4,5-difluorophenyl group], [60; 3-iodo-4,5-difluorophenyl group], [61; 3-fluoro-4,5-dichlorophenyl group], [62; 3-bromo-4,5-dichlorophenyl group], [63; 3-iodo-4,5-dichlorophenyl group], [64; 3-fluoro-4,5-dibromophenyl group], [65; 3-chloro-4,5-dibromophenyl group], [66; 3-iodo-4,5-dibromophenyl group], [67; 3-fluoro-4,5-diiodophenyl group], [68; 3-chloro-4,5-diiodophenyl group], [69; 3-bromo-4,5-diiodophenyl group], [70; 4-chloro-3,5-difluorophenyl group], [71; 4-bromo-3,5-difluorophenyl group], [72; 4-iodo-3,5-difluorophenyl group], [73; 4-fluoro-3,5-dichlorophenyl group], [74; 4-bromo-3,5-dichlorophenyl group], [75; 4-iodo-3,5-dichlorophenyl group], [76; 4-fluoro-3,5-dibromophenyl group], [77; 4-chloro-3,5-dibromophenyl group], [78; 4-iodo-3,5-dibromophenyl group], [79; 4-fluoro-3,5-diiodophenyl group], [80; 4-chloro-3,5-diiodophenyl group], [81; 4-bromo-3,5-diiodophenyl group], [82; 2-methylphenyl group], [83; 3-methylphenyl group], [84; 4-methylphenyl group], [85; 2,3-dimethylphenyl group], [86; 2,4-dimethylphenyl group], [87; 2,5-dimethylphenyl group], [88; 2,6-dimethylphenyl group], [89; 3,4-dimethylphenyl group], [90; 3,5-dimethylphenyl group], [91; 2,3,4-trimethylphenyl group], [92; 2,3,5-trimethylphenyl group], [93; 2,3,6-trimethylphenyl group], [94; 2,4,5-trimethylphenyl group], [95; 2,4,6-trimethylphenyl group], [96; 3,4,5-trimethylphenyl group], [97; 2-ethylphenyl group], [98; 3-ethylphenyl group], [99; 4-ethylphenyl group], [100; 2,3-diethylphenyl group], [101; 2,4-diethylphenyl group], [102; 2,5-diethylphenyl group], [103; 2,6-diethylphenyl group], [104; 3,4-diethylphenyl group], [105; 3,5-diethylphenyl group], [106; 2,3,4-triethylphenyl group], [107; 2,3,5-triethylphenyl group], [108; 2,3,6-triethylphenyl group], [109; 2,4,5-triethylphenyl group], [110; 2,4,6-triethylphenyl group], [111; 3,4,5-triethylphenyl group], [112; 3-propylphenyl group], [113; 4-propylphenyl group], [114; 3,4-dipropylphenyl group], [115; 3,5-dipropylphenyl group], [116; 3,4,5-tripropylphenyl group], [117; 3-isopropylphenyl group], [118; 4-isopropylphenyl group], [119; 3,4-diisopropylphenyl group], [120; 3,5-diisopropylphenyl group], [121; 3,4,5-triisopropylphenyl group], [122; 3-butylphenyl group], [123; 4-butylphenyl group], [124; 3,4-dibutylphenyl group], [125; 3,5-dibutylphenyl group], [126; 3-sec-butylphenyl group], [127; 4-sec-butylphenyl group], [128; 3,4-di-sec-butylphenyl group], [129; 3,5-di-sec-butylphenyl group], [130; 3-isobutylphenyl group], [131; 4-isobutylphenyl group], [132; 3,4-diisobutylphenyl group], [133; 3,5-diisobutylphenyl group], [134; 3-tert-butylphenyl group], [135; 4-tert-butylphenyl group], [136; 3,4-di-tert-butylphenyl group], [137; 3,5-di-tert-butylphenyl group], [138; 3-cyclopropylphenyl group], [139; 4-cyclopropylphenyl group], [140; 3,4-dicyclopropylphenyl group], [141; 3,5-dicyclopropylphenyl group], [142; 3-cyclobutylphenyl group], [143; 4-cyclobutylphenyl group], [144; 3,4-dicyclobutylphenyl group], [145; 3,5-dicyclobutylphenyl group], [146; 3-vinylphenyl group], [147; 4-vinylphenyl group], [148; 3-(1-propenyl)phenyl group], [149; 4-(1-propenyl)phenyl group], [150; 3-(2-propenyl)phenyl group], [151; 4-(2-propenyl)phenyl group], [152; 3-(1-butenyl)phenyl group], [153; 4-(1-butenyl)phenyl group], [154; 3-(2-butenyl)phenyl group], [155; 4-(2-butenyl)phenyl group], [156; 3-(3-butenyl)phenyl group], [157; 4-(3-butenyl)phenyl group], [158; 3-(1-methyl-1-propynyl)phenyl group], [159; 4-(1-methyl-1-propynyl)phenyl group], [160; 3-(1-ethyl-1-ethynyl)phenyl group], [161; 4-(1-ethyl-1-ethynyl)phenyl group], [162; 3-(2-methyl-1-propynyl)phenyl group], [163; 4-(2-methyl-1-propynyl)phenyl group], [164; 3-(2-methyl-2-propynyl)phenyl group], [165; 4-(2-methyl-2-propynyl)phenyl group], [166; 3-ethynylphenyl group], [167; 4-ethynylphenyl group], [168; 3-(1-propynyl)phenyl group], [169; 4-(1-propynyl)phenyl group], [170; 3-(2-propynyl)phenyl group], [171; 4-(2-propynyl)phenyl group], [172; 3-(1-butynyl)phenyl group], [173; 4-(1-butynyl)phenyl group], [174; 3-(2-butynyl)phenyl group], [175; 4-(2-butynyl)phenyl group], [176; 3-(3-butynyl)phenyl group], [177; 4-(3-butynyl)phenyl group], [178; 3-(1-methyl-2-propynyl)phenyl group], [179; 4-(1-methyl-2-propynyl)phenyl group], [180; 3-methoxyphenyl group], [181; 4-methoxyphenyl group], [182; 3-ethoxyphenyl group], [183; 4-ethoxyphenyl group], [184; 3-propoxyphenyl group], [185; 4-propoxyphenyl group], [186; 3-isopropoxyphenyl group], [187; 4-isopropoxyphenyl group], [188; 3-cyclopropoxyphenyl group], [189; 4-cyclopropoxyphenyl group], [190; 3-butoxyphenyl group], [191; 4-butoxyphenyl group], [192; 3-sec-butoxyphenyl group], [193; 4-sec-butoxyphenyl group], [194; 3-isobutoxyphenyl group], [195; 4-isobutoxyphenyl group], [196; 3-tert-butoxyphenyl group], [197; 4-tert-butoxyphenyl group], [198; 3,4-dimethoxyphenyl group], [199; 3,5-dimethoxyphenyl group], [200; 3,4,5-trimethoxyphenyl group], [201; 3-vinyloxyphenyl group], [202; 4-vinyloxyphenyl group], [203; 3-(1-propenyloxyl)phenyl group], [204; 4-(1-propenyloxyl)phenyl group], [205; 3-(2-propenyloxyl)phenyl group], [206; 4-(2-propenyloxyl)phenyl group], [207; 3-(1-butenyloxyl)phenyl group], [208; 4-(1-butenyloxyl)phenyl group], [209; 3-(2-butenyloxyl)phenyl group], [210; 4-(2-butenyloxyl)phenyl group], [211; 3-(3-butenyloxyl)phenyl group], [212; 4-(3-butenyloxyl)phenyl group], [213; 3-(1-methyl-1-propynyloxy)phenyl group], [214; 4-(1-methyl-1-propynyloxy)phenyl group], [215; 3-(1-ethyl-1-ethynyloxy)phenyl group], [216; 4-(1-ethyl-1-ethynyloxy)phenyl group], [217; 3-(2-methyl-1-propynyloxy)phenyl group], [218; 4-(2-methyl-1-propynyloxy)phenyl group], [219; 3-(2-methyl-2-propynyloxy)phenyl group], [220; 4-(2-methyl-2-propynyloxy)phenyl group], [221; 3-methoxymethylphenyl group], [222; 4-methoxymethylphenyl group], [223; 3-fluoromethylphenyl group], [224; 4-fluoromethylphenyl group], [225; 3-difluoromethylphenyl group], [226; 4-difluoromethylphenyl group], [227; 3-trifluoromethylphenyl group], [228; 4-trifluoromethylphenyl group], [229; 3-(1-fluoroethyl)phenyl group], [230; 4-(1-fluoroethyl)phenyl group], [231; 3-(2-fluoroethyl)phenyl group], [232; 4-(2-fluoroethyl)phenyl group], [233; 3-(1,1-difluoroethyl)phenyl group], [234; 4-(1,1-difluoroethyl)phenyl group], [235; 3-(1,2-difluoroethyl)phenyl group], [236; 4-(1,2-difluoroethyl)phenyl group], [237; 3-(2,2-difluoroethyl)phenyl group], [238; 4-(2,2-difluoroethyl)phenyl group], [239; 3-(1,1,2-trifluoroethyl)phenyl group], [240; 4-(1,1,2-trifluoroethyl)phenyl group], [241; 3-(1,2,2-trifluoroethyl)phenyl group], [242; 4-(1,2,2-trifluoroethyl)phenyl group], [243; 3-(2,2,2-trifluoroethyl)phenyl group], [244; 4-(2,2,2-trifluoroethyl)phenyl group], [245; 3-(1,1,2,2-tetrafluoroethyl)phenyl group], [246; 4-(1,1,2,2-tetrafluoroethyl)phenyl group], [247; 3-perfluoroethylphenyl group], [248; 4-perfluoroethylphenyl group], [249; 3-(1-fluoropropyl)phenyl group], [250; 4-(1-fluoropropyl)phenyl group], [251; 3-(2-fluoropropyl)phenyl group], [252; 4-(2-fluoropropyl)phenyl group], [253; 3-(3-fluoropropyl)phenyl group], [254; 4-(3-fluoropropyl)phenyl group], [255; 3-(1,1-difluoropropyl)phenyl group], [256; 4-(1,1-difluoropropyl)phenyl group], [257; 3-(1,2-difluoropropyl)phenyl group], [258; 4-(1,2-difluoropropyl)phenyl group], [259; 3-(1,3-difluoropropyl)phenyl group], [260; 4-(1,3-difluoropropyl)phenyl group], [261; 3-(2,2-difluoropropyl)phenyl group], [262; 4-(2,2-difluoropropyl)phenyl group], [263; 3-(2,3-difluoropropyl)phenyl group], [264; 4-(2,3-difluoropropyl)phenyl group], [265; 3-(3,3-difluoropropyl)phenyl group], [266; 4-(3,3-difluoropropyl)phenyl group], [267; 3-(1,1,2-trifluoropropyl)phenyl group], [268; 4-(1,1,2-trifluoropropyl)phenyl group], [269; 3-(1,1,3-trifluoropropyl)phenyl group], [270; 4-(1,1,3-trifluoropropyl)phenyl group], [271; 3-(1,2,2-trifluoropropyl)phenyl group], [272; 4-(1,2,2-trifluoropropyl)phenyl group], [273; 3-(1,2,3-trifluoropropyl)phenyl group], [274; 4-(1,2,3-trifluoropropyl)phenyl group], [275; 3-(1,3,3-trifluoropropyl)phenyl group], [276; 4-(1,3,3-trifluoropropyl)phenyl group], [277; 3-(2,2,3-trifluoropropyl)phenyl group], [278; 4-(2,2,3-trifluoropropyl)phenyl group], [279; 3-(2,3,3-trifluoropropyl)phenyl group], [280; 4-(2,3,3-trifluoropropyl)phenyl group], [281; 3-(3,3,3-trifluoropropyl)phenyl group], [282; 4-(3,3,3-trifluoropropyl)phenyl group], [283; 3-(1,1,2,2-tetrafluoropropyl)phenyl group], [284; 4-(1,1,2,2-tetrafluoropropyl)phenyl group], [285; 3-(1,1,3,3-tetrafluoropropyl)phenyl group], [286; 4-(1,1,3,3-tetrafluoropropyl)phenyl group], [287; 3-(2,2,3,3-tetrafluoropropyl)phenyl group], [288; 4-(2,2,3,3-tetrafluoropropyl)phenyl group], [289; 3-(1,1,3,3,3-pentafluoropropyl)phenyl group], [290; 4-(1,1,3,3,3-pentafluoropropyl)phenyl group], [291; 3-(2,2,3,3,3-pentafluoropropyl)phenyl group], [92; 4-(2,2,3,3,3-pentafluoropropyl)phenyl group], [293; 3-(1,1,2,2,3,3-hexafluoropropyl)phenyl group], [294; 4-(1,1,2,2,3,3-hexafluoropropyl)phenyl group], [295; 3-perfluoropropylphenyl group], [296; 4-perfluoropropylphenyl group], [297; 3-perfluoropropylphenyl group], [298; 4-perfluoropropylphenyl group], [299; 3-(2,2,2,2,2,2-hexafluoroisopropyl)phenyl group], [300; 4-(2,2,2,2,2,2-hexafluoroisopropyl)phenyl group], [301; 3-perfluoroisopropylphenyl group], [302; 4-perfluoroisopropylphenyl group], [303; 3-perfluorobutylphenyl group], [304; 4-perfluorobutylphenyl group], [305; 3-perfluoro-sec-butylphenyl group], [306; 4-perfluoro-sec-butylphenyl group], [307; 3-perfluoroisobutylphenyl group], [308; 4-perfluoroisobutylphenyl group], [309; 5-fluoro-3-trifluoromethylphenyl group], [310; 6-fluoro-3-trifluoromethylphenyl group], [311; 2,4-difluoro-3-trifluoromethylphenyl group], [312; 2,5-difluoro-3-trifluoromethylphenyl group], [313; 2,6-difluoro-3-trifluoromethylphenyl group], [314; 4,5-difluoro-3-trifluoromethylphenyl group], [315; 4,6-difluoro-3-trifluoromethylphenyl group], [316; 5,6-difluoro-3-trifluoromethylphenyl group], [317; 2,4,5-trifluoro-3-trifluoromethylphenyl group], [318; 2,4,6-trifluoro-3-trifluoromethylphenyl group], [319; 4,5,6-trifluoro-3-trifluoromethylphenyl group], [320; 2,4,5,6-tetrafluoro-3-trifluoromethylphenyl group], [321; 4-chloro-3-trifluoromethylphenyl group], [322; 5-chloro-3-trifluoromethylphenyl group], [323; 4-methyl-3-trifluoromethylphenyl group], [324; 5-methyl-3-trifluoromethylphenyl group], [325; 4-ethyl-3-trifluoromethylphenyl group], [326; 5-ethyl-3-trifluoromethylphenyl group], [327; 4-cyclopropyl-3-trifluoromethylphenyl group], [328; 5-cyclopropyl-3-trifluoromethylphenyl group], [329; 4-methoxy-3-trifluoromethylphenyl group], [330; 5-methoxy-3-trifluoromethylphenyl group], [331; 3-fluoromethoxyphenyl group], [332; 4-fluoromethoxyphenyl group], [333; 3-difluoromethoxyphenyl group], [334; 4-difluoromethoxyphenyl group], [335; 3-trifluoromethoxyphenyl group], [336; 4-trifluoromethoxyphenyl group], [337; 3-(1-fluoroethoxyl)phenyl group], [338; 4-(1-fluoroethoxyl)phenyl group], [339; 3-(2-fluoroethoxyl)phenyl group], [340; 4-(2-fluoroethoxyl)phenyl group], [341; 3-(1,1-difluoroethoxyl)phenyl group], [342; 4-(1,1-difluoroethoxyl)phenyl group], [343; 3-(1,2-difluoroethoxyl)phenyl group], [344; 4-(1,2-difluoroethoxyl)phenyl group], [345; 3-(2,2-difluoroethoxyl)phenyl group], [346; 4-(2,2-difluoroethoxyl)phenyl group], [347; 3-(1,1,2-trifluoroethoxyl)phenyl group], [348; 4-(1,1,2-trifluoroethoxy)phenyl group], [349; 3-(1,2,2-trifluoroethoxyl)phenyl group], [350; 4-(1,2,2-trifluoroethoxyl)phenyl group], [351; 3-(2,2,2-trifluoroethoxyl)phenyl group], [352; 4-(2,2,2-trifluoroethoxyl)phenyl group], [353; 3-(1,1,2,2-tetrafluoroethoxyl)phenyl group], [354; 4-(1,1,2,2-tetrafluoroethoxyl)phenyl group], [355; 3-(perfluoroethoxy)phenyl group], [356; 4-(perfluoroethoxy)phenyl group], [357; 3-(1-fluoropropoxyl)phenyl group], [358; 4-(1-fluoropropoxyl)phenyl group], [359; 3-(2-fluoropropoxyl)phenyl group], [360; 4-(2-fluoropropoxyl)phenyl group], [361; 3-(3-fluoropropoxyl)phenyl group], [362; 4-(3-fluoropropoxyl)phenyl group], [363; 3-(1,1-difluoropropoxyl)phenyl group], [364; 4-(1,1-difluoropropoxyl)phenyl group], [365; 3-(1,2-difluoropropoxyl)phenyl group], [366; 4-(1,2-difluoropropoxyl)phenyl group], [367; 3-(1,3-difluoropropoxyl)phenyl group], [368; 4-(1,3-difluoropropoxyl)phenyl group], [369; 3-(2,2-difluoropropoxyl)phenyl group], [370; 4-(2,2-difluoropropoxyl)phenyl group], [371; 3-(2,3-difluoropropoxyl)phenyl group], [372; 4-(2,3-difluoropropoxyl)phenyl group], [373; 3-(3,3-difluoropropoxyl)phenyl group], [374; 4-(3,3-difluoropropoxyl)phenyl group], [375; 3-(1,1,2-trifluoropropoxyl)phenyl group], [376; 4-(1,1,2-trifluoropropoxyl)phenyl group], [377; 3-(1,1,3-trifluoropropoxyl)phenyl group], [378; 4-(1,1,3-trifluoropropoxyl)phenyl group], [379; 3-(1,2,2-trifluoropropoxyl)phenyl group], [380; 4-(1,2,2-trifluoropropoxyl)phenyl group], [381; 3-(1,2,3-trifluoropropoxyl)phenyl group], [382; 4-(1,2,3-trifluoropropoxyl)phenyl group], [383; 3-(1,3,3-trifluoropropoxyl)phenyl group], [384; 4-(1,3,3-trifluoropropoxyl)phenyl group], [385; 3-(2,2,3-trifluoropropoxyl)phenyl group], [386; 4-(2,2,3-trifluoropropoxyl)phenyl group], [387; 3-(2,3,3-trifluoropropoxyl)phenyl group], [388; 4-(2,3,3-trifluoropropoxyl)phenyl group], [389; 3-(3,3,3-trifluoropropoxyl)phenyl group], [390; 4-(3,3,3-trifluoropropoxyl)phenyl group], [391; 3-(1,1,2,2-tetrafluoropropoxyl)phenyl group], [392; 4-(1,1,2,2-tetrafluoropropoxyl)phenyl group], [393; 3-(1,1,3,3-tetrafluoropropoxyl)phenyl group], [394; 4-(1,1,3,3-tetrafluoropropoxyl)phenyl group], [395; 3-(2,2,3,3-tetrafluoropropoxyl)phenyl group], [396; 4-(2,2,3,3-tetrafluoropropoxyl)phenyl group], [397; 3-(1,1,3,3,3-pentafluoropropoxyl)phenyl group], [398; 4-(1,1,3,3,3-pentafluoropropoxyl)phenyl group], [399; 3-(2,2,3,3,3-pentafluoropropoxyl)phenyl group], [400; 4-(2,2,3,3,3-pentafluoropropoxyl)phenyl group], [401; 3-(1,1,2,2,3,3-hexafluoropropoxyl)phenyl group], [402; 4-(1,1,2,2,3,3-hexafluoropropoxyl)phenyl group], [403; 3-perfluoropropoxyphenyl group], [404; 4-perfluoropropoxyphenyl group], [407; 3-(2,2,2,2,2,2-hexafluoroisopropoxyl)phenyl group], [408; 4-(2,2,2,2,2,2,2-hexafluoroisopropoxyl)phenyl group], [409; 3-perfluoroisopropoxyphenyl group], [410; 4-perfluoroisopropoxyphenyl group], [411; 3-perfluorobutoxyphenyl group], [412; 4-perfluorobutoxyphenyl group], [413; 3-perfluoro-sec-butoxyphenyl group], [414; 4-perfluoro-sec-butoxyphenyl group], [415; 3-perfluoroisobutoxyphenyl group], [416; 4-perfluoroisobutoxyphenyl group], [417; 4-chloro-3-trifluoromethoxyphenyl group], [418; 5-chloro-3-trifluoromethoxyphenyl group], [419; 4-methyl-3-trifluoromethoxyphenyl group], [420; 5-methyl-3-trifluoromethoxyphenyl group], [421; 4-ethyl-3-trifluoromethoxyphenyl group], [422; 5-ethyl-3-trifluoromethoxyphenyl group], [423; 4-cyclopropyl-3-trifluoromethoxyphenyl group], [424; 5-cyclopropyl-3-trifluoromethoxyphenyl group], [425; 4-methoxy-3-trifluoromethoxyphenyl group], [426; 5-methoxy-3-trifluoromethoxyphenyl group], [427; 3-nitrophenyl group], [428; 4-nitrophenyl group], [429; 3-cyanophenyl group], [430; 4-cyanophenyl group], [431; 3-methylthiophenyl group], [432; 4-methylthiophenyl group], [433; 3-trifluoromethylthiophenyl group], [434; 4-trifluoromethylthiophenyl group], [435; 3-aminophenyl group], [436; 4-aminophenyl group], [437; 3-(N-methylamino)phenyl group], [438; 4-(N-methylamino)phenyl group], [439; 3-(N,N-dimethylamino)phenyl group], [440; 4-(N,N-dimethylamino)phenyl group], [441; 3-(N-ethylamino)phenyl group], [442; 4-(N-ethylamino)phenyl group], [443; 3-(N,N-diethylamino)phenyl group], [444; 4-(N,N-diethylamino)phenyl group], [445; 3-(N-ethyl-N-methylamino)phenyl group], [446; 4-(N-ethyl-N-methylamino)phenyl group], [447; 3-(N-propylamino)phenyl group], [448; 4-(N-propylamino)phenyl group], [449; 3-(N-propylamino)phenyl group], [450; 4-(N-propylamino)phenyl group], [451; 3-(N-isopropylamino)phenyl group], [452; 4-(N-isopropylamino)phenyl group], [453; 3-(N,N-diisopropylamino)phenyl group], [454; 4-(N,N-diisopropylamino)phenyl group], [455; 3-phenol group], [456; 4-phenol group], [457; 3-methylthiophenyl group], [458; 4-methylthiophenyl group], [459; 3-(N-fluoromethylamino)phenyl group], [460; 4-(N-fluoromethylamino)phenyl group], [461; 3-(N-difluoromethylamino)phenyl group], [462; 4-(N-difluoromethylamino)phenyl group], [463; 3-(N-trifluoromethylamino)phenyl group], [464; 4-(N-trifluoromethylamino)phenyl group], [465; 3-methylcarbonylphenyl group], [466; 4-methylcarbonylphenyl group], [467; 3-ethylcarbonylphenyl group], [468; 4-ethylcarbonylphenyl group], [469; 3-methoxycarbonylphenyl group], [470; 4-methoxycarbonylphenyl group], [471; 3-ethoxycarbonylphenyl group], [472; 4-ethoxycarbonylphenyl group], [473; 3-aminocarbonylphenyl group], [474; 4-aminocarbonylphenyl group], [475; 3-methylaminocarbonylphenyl group], [476; 4-methylaminocarbonylphenyl group], [477; 3-(N-formylamino)phenyl group], [478; 4-(N-formylamino)phenyl group], [479; 3-(N-formyl-N-methylamino)phenyl group], [480; 4-(N-formyl-N-methylamino)phenyl group], [481; 3-trimethylsilylphenyl group], [482; 4-trimethylsilylphenyl group], [483; 1-naphthyl group], [484; 2-naphthyl group], [485; indan-1-yl group], [486; indan-2-yl group], [487; 1-(5,6,7,8-tetrahydro)naphthyl group], [488; 2-(5,6,7,8-tetrahydro)naphthyl group], [489; cyclohexenyl group], [490; cyclohexyl group], [491; 2-chlorocyclohex-1-enyl group], [492; 2-methylcyclohex-1-enyl group], [493; 4-chlorocyclohex-1-enyl group], [494; 4-methylcyclohex-1-enyl group], [495; 6-chlorocyclohex-1-enyl group], [496; 6-methylcyclohex-1-enyl group], [497; 3-chlorocyclohex-1-enyl group], [498; 3-methylcyclohex-1-enyl group], [499; 3-methoxycyclohex-1-enyl group], [500; 3-trifluoromethylcyclohex-1-enyl group], [501; 3-difluoromethylcyclohex-1-enyl group], [502; 3-trifluoromethoxycyclohex-1-enyl group], [503; 5-chlorocyclohex-1-enyl group], [504; 5-methylcyclohex-1-enyl group], [505; 5-methoxycyclohex-1-enyl group], [506; 5-trifluoromethylcyclohex-1-enyl group], [507; 5-difluoromethylcyclohex-1-enyl group], [508; 5-trifluoromethoxycyclohex-1-enyl group], [509; butyl-1-enyl group], [510; 3-methylbut-1-enyl group], [511; 4-chloro-3-chloromethylbut-1-enyl group], [512; 3-chlorocyclohexyl group], and [513; 3-trifluoromethylcyclohexyl group].

(1265) According to the above method, the compounds EP13A-001 to EP18C-513 can be obtained.

(1266) The compounds EP13A-001 to EP16C-513 will be shown below:

(1267) ##STR00574## ##STR00575## ##STR00576##
wherein Q is a compound corresponding to each of substituent numbers 1 to 513.

(1268) According to the above method, it is possible to obtain compounds EP1A-1001 to EP1C-3047, EP2A-1001 to EP2C-3047, EP3A-1001 to EP3C-3047, EP4A-1001 to EP4C-3047, EP5A-1001 to EP5C-3047, EP6A-1001 to EP6C-3047, EP7A-1001 to EP7C-3047, EP8A-1001 to EP8C-3047, EP9A-1001 to EP9C-3047, EP10A-1001 to EP10C-3047, EP11A-1001 to EP11C-3047, EP12A-1001 to EP12C-3047, EP13A-1001 to EP13C-3047, EP14A-1001 to EP14C-3047, EP15A-1001 to EP15C-3047, and EP16A-1001 to EP16C-3047:

(1269) ##STR00577## ##STR00578## ##STR00579## ##STR00580## ##STR00581## ##STR00582## ##STR00583## ##STR00584## ##STR00585## ##STR00586## ##STR00587##
wherein Q represents any one of substituent numbers 1001 to 3047, Q.sup.q1 to Q.sup.v10 represent any one of the followings; and the symbol ∘ represents a binding site.

(1270) Substituent numbers 1001 to 3047 will be shown below.

(1271) Here, Me represents a methyl group, OMe represents a methoxy group, CF.sub.3 represents a trifluoromethyl group, OCF.sub.3 represents a trifluoromethoxy group, OCHF.sub.2 represents a difluoromethoxy group, for example, [1001; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=H, R.sup.12=H] represents a group in which Q is Q.sup.q1, A.sup.1, A.sup.2, A.sup.3, A.sup.4, A.sup.5, A.sup.6, R.sup.3, R.sup.11, and R.sup.12 are hydrogen atoms, and a compound in which the substituent number is 1,001 in EP1A represents the following compound:

(1272) ##STR00588## wherein substituent number; Q
[1001; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1002; Q=Q.sup.q1, .sup.1=F, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1003; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1004; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=F, A.sup.6=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1005; Q=Q.sup.q1, A.sup.1=F, A.sup.2=F, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1006; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1007; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=F, A.sup.6=F, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1008; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1009; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Cl, A.sup.6=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1010; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1011; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Cl, A.sup.6=Cl, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1012; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Br, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1013; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Br, A.sup.6=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1014; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Br, A.sup.4=Br, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1015; Q=Q.sup.q1, A.sup.5=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Br, A.sup.6=Br, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1016; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1017; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Me, A.sup.6=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1018; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1019; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Me, A.sup.6=Me, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1020; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=OMe, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1021; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=OMe, A.sup.6=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1022; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1023; Q=Q.sup.p1, A.sup.1=F, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1024; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1025; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=F, A.sup.6=H, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1026; Q=Q.sup.q1, A.sup.1=F, A.sup.2=F, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1027; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, A.sup.5=H, A.sup.6=H, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1028; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=F, A.sup.6=F, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1029; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1030; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Cl, A.sup.6=H, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1031; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, A.sup.5=H, A.sup.6=H, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1032; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Cl, A.sup.6=Cl, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1033; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Br, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1034; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Br, A.sup.6=H, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1035; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Br, A.sup.4=Br, A.sup.5=H, A.sup.6=H, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1036; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Br, A.sup.6=Br, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1037; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1038; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Me, A.sup.6=H, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1039; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, A.sup.5=H, A.sup.6=H, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1040; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Me, A.sup.6=Me, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1041; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=OMe, A.sup.6=H, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1043; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1044; Q=Q.sup.q1, A.sup.1=F, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=C, R.sup.11=H, R.sup.12=H], [1045; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1046; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=F, A.sup.6=H, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1047; Q=Q.sup.q1, A.sup.1=F, A.sup.2=F, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1048; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, A.sup.5=H, A.sup.6=H, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1049; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=F, A.sup.6=F, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1050; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1051; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Cl, A.sup.6=H, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1052; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, A.sup.5=H, A.sup.6=H, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1053; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Cl, A.sup.6=Cl, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1054; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Br, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1055; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Br, A.sup.6=H, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1056; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Br, A.sup.4=Br, A.sup.5=H, A.sup.6=H, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1057; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Br, A.sup.6=Br, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1058; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1059; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Me, A.sup.6=H, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1060; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, A.sup.5=H, A.sup.6=H, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1061; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Me, A.sup.6=Me, R.sup.3=C, R.sup.11=H, R.sup.12=H], [1062; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=OMe, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=C, R.sup.11=H, R.sup.12=H], [1063; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=OMe, A.sup.6=H, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1064; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=Br, R.sup.11=H, R.sup.12=H], [1065; Q=Q.sup.q1, A.sup.1=F, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=Br, R.sup.11=H, R.sup.12=H], [1066; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=Br, R.sup.11=H, R.sup.12=H], [1067; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=F, A.sup.6=H, R.sup.3=Br, R.sup.11=H, R.sup.12=H], [1068; Q=Q.sup.q1, A.sup.1=F, A.sup.2=F, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=Br, R.sup.11=H, R.sup.12=H], [1069; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, A.sup.5=H, A.sup.6=H, R.sup.3=Br, R.sup.11=H, R.sup.12=H], [1070; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=F, A.sup.6=F, R.sup.3=Br, R.sup.11=H, R.sup.12=H], [1071; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=Br, R.sup.11=H, R.sup.12=H], [1072; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Cl, A.sup.6=H, R.sup.3=Br, R.sup.11=H, R.sup.12=H], [1073; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, A.sup.5=H, A.sup.6=H, R.sup.3=Br, R.sup.11=H, R.sup.12=H], [1074; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Cl, A.sup.6=Cl, R.sup.3=Br, R.sup.11=H, R.sup.12=H], [1075; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Br, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=Br, R.sup.11=H, R.sup.12=H], [1076; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Br, A.sup.6=H, R.sup.3=Br, R.sup.11=H, R.sup.12=H], [1077; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Br, A.sup.4=Br, A.sup.5=H, A.sup.6=H, R.sup.3=Br, R.sup.11=H, R.sup.12=H], [1078; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Br, A.sup.6=Br, R.sup.3=Br, R.sup.11=H, R.sup.12=H], [1079; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=Br, R.sup.11=H, R.sup.12=H], [1080; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Me, A.sup.6=H, R.sup.3=Br, R.sup.11=H, R.sup.12=H], [1081; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, A.sup.5=H, A.sup.6=H, R.sup.3=Br, R.sup.11=H, R.sup.12=H], [1082; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Me, A.sup.6=Me, R.sup.3=Br, R.sup.11=H, R.sup.12=H], [1083; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=OMe, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=Br, R.sup.11=H, R.sup.12=H], [1084; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=OMe, A.sup.6=H, R.sup.3=Br, R.sup.11=H, R.sup.12=H], [1085; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1086; Q=Q.sup.q1, A.sup.1=F, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1087; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1088; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=F, A.sup.6=H, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1089; Q=Q.sup.q1, A.sup.1=F, A.sup.2=F, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1090; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, A.sup.5=H, A.sup.6=H, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1091; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=F, A.sup.6=F, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1092; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=C, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1093; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Cl, A.sup.6=H, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1094; Q=Q.sup.q1, A.sup.11=H, A.sup.2=H, A.sup.3=C, A.sup.4=C, A.sup.5=H, A.sup.6=H, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1095; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Cl, A.sup.6=Cl, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1096; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Br, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1097; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Br, A.sup.6=H, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1098; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Br, A.sup.4=Br, A.sup.5=H, A.sup.6=H, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1099; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Br, A.sup.6=Br, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1100; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1101; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Me, A.sup.6=H, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1102; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, A.sup.5=H, A.sup.6=H, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1103; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Me, A.sup.6=Me, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1104; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=OMe, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1105; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=OMe, A.sup.6=H, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1106; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1107; Q=Q.sup.q1, A.sup.1=F, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1108; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1109; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=F, A.sup.6=H, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1110; Q=Q.sup.q1, A.sup.1=F, A.sup.2=F, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1111; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, A.sup.5=H, A.sup.6=H, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1112; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=F, A.sup.6=F, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1113; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1114; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Cl, A.sup.6=H, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1115; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=C, A.sup.5=H, A.sup.6=H, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1116; Q=Q.sup.q1, A.sup.11=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Cl, A.sup.6=Cl, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1117; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Br, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1118; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Br, A.sup.6=H, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1119; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Br, A.sup.4=Br, A.sup.5=H, A.sup.6=H, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1120; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Br, A.sup.6=Br, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1121; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1122; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Me, A.sup.6=H, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1123; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, A.sup.5=H, A.sup.6=H, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1124; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Me, A.sup.6=Me, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1125; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=OMe, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1126; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=OMe, A.sup.6=H, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1127; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1128; Q=Q.sup.q1, A.sup.1=F, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1129; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1130; Q=Q.sup.q1, A.sup.11=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=F, A.sup.6=H, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1131; Q=Q.sup.q1, A.sup.1=F, A.sup.2=F, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1132; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, A.sup.5=H, A.sup.6=H, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1133; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=F, A.sup.6=F, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1134; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=C, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1135; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Cl, A.sup.6=H, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1136; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, A.sup.5=H, A.sup.6=H, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1137; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Cl, A.sup.6=Cl, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1138; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Br, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1139; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Br, A.sup.6=H, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1140; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Br, A.sup.4=Br, A.sup.5=H, A.sup.6=H, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1141; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Br, A.sup.6=Br, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1142; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1143; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Me, A.sup.6=H, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1144; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, A.sup.5=H, A.sup.6=H, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1145; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Me, A.sup.6=Me, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1146; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=OMe, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1147; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=OMe, A.sup.6=H, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1148; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=OCF.sub.3, R.sup.11=H, R.sup.12=H], [1149; Q=Q.sup.q1, A.sup.1=F, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=OCF.sub.3, R.sup.11=H, R.sup.12=H], [1150; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=OCF.sub.3, R.sup.11=H, R.sup.12=H], [1151; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=F, A.sup.6=H, R.sup.3=OCF.sub.3, R.sup.11=H, R.sup.12=H], [1152; Q=Q.sup.q1, A.sup.1=F, A.sup.2=F, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=OCF.sub.3, R.sup.11=H, R.sup.12=H], [1153; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, A.sup.5=H, A.sup.6=H, R.sup.3=OCF.sub.3, R.sup.11=H, R.sup.12=H], [1154; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=F, A.sup.6=F, R.sup.3=OCF.sub.3, R.sup.11=H, R.sup.12=H], [1155; Q=Q.sup.q1, A.sup.11=H, A.sup.2=H, A.sup.3=C, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=OCF.sub.3, R.sup.11=H, R.sup.12=H], [1156; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Cl, A.sup.6=H, R.sup.3=OCF.sub.3, R.sup.11=H, R.sup.12=H], [1157; Q=Q.sup.q1, A.sup.11=H, A.sup.2=H, A.sup.3=C, A.sup.4=C, A.sup.5=H, A.sup.6=H, R.sup.3=OCF.sub.3, R.sup.11=H, R.sup.12=H], [1158; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Cl, A.sup.6=Cl, R.sup.3=OCF.sub.3, R.sup.11=H, R.sup.12=H], [1159; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Br, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=OCF.sub.3, R.sup.11=H, R.sup.12=H], [1160; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Br, A.sup.6=H, R.sup.3=OCF.sub.3, R.sup.11=H, R.sup.12=H], [1161; Q=Q.sup.q1, A.sup.11=H, A.sup.2=H, A.sup.3=Br, A.sup.4=Br, A.sup.5=H, A.sup.6=H, R.sup.3=OCF.sub.3, R.sup.11=H, R.sup.12=H], [1162; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Br, A.sup.6=Br, R.sup.3=OCF.sub.3, R.sup.11=H, R.sup.12=H], [1163; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=OCF.sub.3, R.sup.11=H, R.sup.12=H], [1164; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Me, A.sup.6=H, R.sup.3=OCF.sub.3, R.sup.11=H, R.sup.12=H], [1165; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, A.sup.5=H, A.sup.6=H, R.sup.3=OCF.sub.3, R.sup.11=H, R.sup.12=H], [1166; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Me, A.sup.6=Me, R.sup.3=OCF.sub.3, R.sup.11=H, R.sup.12=H], [1167; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=OMe, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=OCF.sub.3, R.sup.11=H, R.sup.12=H], [1168; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=OMe, A.sup.6=H, R.sup.3=OCF.sub.3, R.sup.11=H, R.sup.12=H], [1169; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1170; Q=Q.sup.q1, A.sup.1=F, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1171; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1172; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=F, A.sup.6=H, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1173; Q=Q.sup.q1, A.sup.1=F, A.sup.2=F, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1174; Q=Q.sup.q1, A.sup.11=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, A.sup.5=H, A.sup.6=H, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1175; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=F, A.sup.6=F, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1176; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1177; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Cl, A.sup.6=H, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1178; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, A.sup.5=H, A.sup.6=H, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1179; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Cl, A.sup.6=Cl, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1180; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Br, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=SMe, R.sup.11=H, R.sup.2=H], [1181; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Br, A.sup.6=H, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1182; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Br, A.sup.4=Br, A.sup.5=H, A.sup.6=H, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1183; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Br, A.sup.6=Br, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1184; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1185; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Me, A.sup.6=H, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1186; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, A.sup.5=H, A.sup.6=H, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1187; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Me, A.sup.6=Me, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1188; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=OMe, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1189; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=OMe, A.sup.6=H, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1190; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=F, R.sup.12=H], [1191; Q=Q.sup.q1, A.sup.1=F, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=F, R.sup.12=H], [1192; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.11=H, R.sup.11=F, R.sup.12=H], [1193; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=F, A.sup.6=H, R.sup.3=H, R.sup.11=F, R.sup.12=H], [1194; Q=Q.sup.q1, A.sup.1=F, A.sup.2=F, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=F, R.sup.12=H], [1195; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=F, R.sup.12=H], [1196; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=F, A.sup.6=F, R.sup.3=H, R.sup.11=F, R.sup.12=H], [1197; Q=Q.sup.q1, A.sup.1=H, A.sup.2=, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=F, R.sup.12=H], [1198; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Cl, A.sup.6=H, R.sup.3=H, R.sup.11=F, R.sup.12=H], [1199; Q=Q 2, A.sup.1=H, A.sup.2=H, A.sup.3=C, A.sup.4=Cl, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=F, R.sup.12=H], [1200; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Cl, A.sup.6=Cl, R.sup.3=H, R.sup.11=F, R.sup.12=H], [1201; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Br, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=F, R.sup.12=H], [1202; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Br, A.sup.6=H, R.sup.3=H, R.sup.11=F, R.sup.12=H], [1203; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Br, A.sup.4=Br, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=F, R.sup.12=H], [1204; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Br, A.sup.6=Br, R.sup.3=H, R.sup.11=F, R.sup.12=H], [1205; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=F, R.sup.12=H], [1206; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Me, A.sup.6=H, R.sup.3=H, R.sup.11=F, R.sup.12=H], [1207; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.1=F, R.sup.12=H], [1208; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Me, A.sup.6=Me, R.sup.3=H, R.sup.1=F, R.sup.12=H], [1209; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=OMe, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=F, R.sup.12=H], [1210; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=OMe, A.sup.6=H, R.sup.3=H, R.sup.11=F, R.sup.12=H], [1211; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1212; Q=Q.sup.q1, A.sup.1=F, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1213; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1214; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=F, A.sup.6=H, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1215; Q=Q.sup.q1, A.sup.1=F, A.sup.2=F, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1216; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1217; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=F, A.sup.6=F, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1218; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1219; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Cl, A.sup.6=H, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1220; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1221; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Cl, A.sup.6=Cl, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1222; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Br, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1223; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Br, A.sup.6=H, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1224; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Br, A.sup.4=Br, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1225; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Br, A.sup.6=Br, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1226; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.6=Me, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1227; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Me, A.sup.6=H, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1228; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1229; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Me, A.sup.6=Me, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1230; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=OMe, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1231; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=OMe, A.sup.6=H, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1232; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.6=H, A.sup.6=H, R.sup.3=H, R.sup.11=Br, R.sup.12=H], [1233; Q=Q.sup.q1, A.sup.1=F, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=Br, R.sup.12=H], [1234; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=Br, R.sup.12=H], [1235; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=F, A.sup.6=H, R.sup.3=H, R.sup.11=Br, R.sup.12=H], [1236; Q=Q.sup.q1, A.sup.1=F, A.sup.2=F, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=Br, R.sup.12=H], [1237; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=Br, R.sup.12=H], [1238; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=F, A.sup.6=F, R.sup.3=H, R.sup.11=Br, R.sup.12=H], [1239; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=Br, R.sup.12=H], [1240; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Cl, A.sup.6=H, R.sup.3=H, R.sup.11=Br, R.sup.12=H], [1241; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=Br, R.sup.12=H], [1242; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Cl, A.sup.6=Cl, R.sup.3=H, R.sup.11=Br, R.sup.12=H], [1243; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Br, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=Br, R.sup.12=H], [1244; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Br, A.sup.6=H, R.sup.3=H, R.sup.11=Br, R.sup.12=H], [1245; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Br, A.sup.4=Br, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=Br, R.sup.12=H], [1246; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Br, A.sup.6=Br, R.sup.3=H, R.sup.11=Br, R.sup.12=H], [1247; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=Br, R.sup.12=H], [1248; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Me, A.sup.6=H, R.sup.3=H, R.sup.11=Br, R.sup.12=H], [1249; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=Br, R.sup.12=H], [1250; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Me, A.sup.6=Me, R.sup.3=H, R.sup.11=Br, R.sup.12=H], [1251; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=OMe, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=Br, R.sup.12=H], [1252; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=OMe, A.sup.6=H, R.sup.3=H, R.sup.11=Br, R.sup.12=H], [1253; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1254; Q=Q.sup.q1, A.sup.1=F, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1255; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1256; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=F, A.sup.6=H, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1257; Q=Q.sup.q1, A.sup.1=F, A.sup.2=F, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1258; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1259; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=F, A.sup.6=F, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1260; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1261; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Cl, A.sup.6=H, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1262; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1263; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Cl, A.sup.6=Cl, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1264; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Br, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1265; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Br, A.sup.6=H, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1266; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Br, A.sup.4=Br, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1267; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Br, A.sup.6=Br, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1268; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1269; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Me, A.sup.6=H, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1270; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1271; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Me, A.sup.6=Me, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1272; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=OMe, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1273; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=OMe, A.sup.6=H, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1274; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1275; Q=Q.sup.q1, A.sup.1=F, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1276; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1277; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=F, A.sup.6=H, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1278; Q=Q.sup.q1, A.sup.1=F, A.sup.2=F, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1279; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1280; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=F, A.sup.6=F, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1281; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1282; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Cl, A.sup.6=H, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1283; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1284; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Cl, A.sup.6=Cl, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1285; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Br, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1286; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Br, A.sup.6=H, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1287; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Br, A.sup.4=Br, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1288; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Br, A.sup.6=Br, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1289; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1290; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Me, A.sup.6=H, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1291; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1292; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Me, A.sup.6=Me, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1293; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=OMe, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1294; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=OMe, A.sup.6=H, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1295; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1296; Q=Q.sup.q1, A.sup.1=F, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1297; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, A.sup.5=H, A.sup.1=H, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1298; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=F, A.sup.6=H, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1299; Q=Q.sup.q1, A.sup.1=F, A.sup.2=F, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1300; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1301; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=F, A.sup.6=F, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1302; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1303; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Cl, A.sup.6=H, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1304; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1305; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Cl, A.sup.6=Cl, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1306; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Br, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1307; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Br, A.sup.6=H, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1308; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Br, A.sup.4=Br, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1309; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Br, A.sup.6=Br, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1310; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1311; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Me, A.sup.6=H, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1312; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1313; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Me, A.sup.6=Me, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1314; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=OMe, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1315; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=OMe, A.sup.6=H, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1316; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=OCF.sub.3, R.sup.12=H], [1317; Q=Q.sup.q1, A.sup.1=F, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=OCF.sub.3, R.sup.12=H], [1318; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=OCF.sub.3, R.sup.12=H], [1319; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=F, A.sup.6=H, R.sup.3=H, R.sup.11=OCF.sub.3, R.sup.12=H], [1320; Q=Q.sup.q1, A.sup.1=F, A.sup.2=F, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=OCF.sub.3, R.sup.12=H], [1321; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=OCF.sub.3, R.sup.12=H], [1322; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=F, A.sup.6=F, R.sup.3=H, R.sup.11=OCF.sub.3, R.sup.12=H], [1323; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=OCF.sub.3, R.sup.12=H], [1324; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Cl, A.sup.6=H, R.sup.3=H, R.sup.11=OCF.sub.3, R.sup.12=H], [1325; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=OCF.sub.3, R.sup.12=H], [1326; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Cl, A.sup.6=Cl, R.sup.3=H, R.sup.11=OCF.sub.3, R.sup.12=H], [1327; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Br, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=OCF.sub.3, R.sup.12=H], [1328; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Br, A.sup.6=H, R.sup.3=H, R.sup.11=OCF.sub.3, R.sup.12=H], [1329; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Br, A.sup.4=Br, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=OCF.sub.3, R.sup.12=H], [1330; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Br, A.sup.6=Br, R.sup.3=H, R.sup.11=OCF.sub.3, R.sup.12=H], [1331; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=OCF.sub.3, R.sup.12=H], [1332; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Me, A.sup.6=H, R.sup.3=H, R.sup.11=OCF.sub.3, R.sup.12=H], [1333; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=OCF.sub.3, R.sup.12=H], [1334; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Me, A.sup.6=Me, R.sup.3=H, R.sup.11=OCF.sub.3, R.sup.12=H], [1335; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=OMe, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=OCF.sub.3, R.sup.12=H], [1336; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=OMe, A.sup.6=H, R.sup.3=H, R.sup.11=OCF.sub.3, R.sup.12=H], [1337; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], [1338; Q=Q.sup.q1, A.sup.1=F, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], [1339; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], [1340; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=F, A.sup.6=H, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], [1341; Q=Q.sup.q1, A.sup.1=F, A.sup.2=F, A.sup.3=H, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], [1342; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], [1343; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=F, A.sup.6=F, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], [1344; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], [1345; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Cl, A.sup.6=H, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], [1346; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], [1347; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Cl, A.sup.6=Cl, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], [1348; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Br, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], [1349; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Br, A.sup.6=H, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], [1350; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Br, A.sup.4=Br, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], [1351; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Br, A.sup.6=Br, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], [1352; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], [1353; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Me, A.sup.6=H, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], [1354; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], [1355; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=Me, A.sup.6=Me, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], [1356; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=OMe, A.sup.4=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], [1357; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.5=OMe, A.sup.6=H, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], [1358; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1359; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1360; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1361; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1362; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1363; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1364; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1395; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1396; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1397; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1398; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1399; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1400; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1401; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1402; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1403; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1404; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1405; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1406; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1407; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1408; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1409; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=Br, R.sup.11=H, R.sup.12=H], [1410; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, R.sup.3=Br, R.sup.11=H, R.sup.12=H], [1411; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, R.sup.3=Br, R.sup.11=H, R.sup.12=H], [1412; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, R.sup.3=Br, R.sup.11=H, R.sup.12=H], [1413; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, R.sup.3=Br, R.sup.11=H, R.sup.12=H], [1414; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, R.sup.3=Br, R.sup.11=H, R.sup.12=H], [1415; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, R.sup.3=Br, R.sup.11=H, R.sup.12=H], [1416; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1417; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1418; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1419; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1420; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1421; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1422; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1423; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1424; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1425; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1426; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1427; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1428; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1429; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1430; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1431; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1432; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1433; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1434; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1435; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1436; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1437; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=OCF.sub.3, R.sup.11=H, R.sup.12=H], [1438; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, R.sup.3=OCF.sub.3, R.sup.11=H, R.sup.12=H], [1439; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, R.sup.3=OCF.sub.3, R.sup.11=H, R.sup.12=H], [1440; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, R.sup.3=OCF.sub.3, R.sup.11=H, R.sup.12=H], [1441; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, R.sup.3=OCF.sub.3, R.sup.11=H, R.sup.12=H], [1442; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, R.sup.3=OCF.sub.3, R.sup.11=H, R.sup.12=H], [1443; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, R.sup.3=OCF.sub.3, R.sup.11=H, R.sup.12=H], [1444; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1445; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, R.sup.3=SMe, R.sup.11=H, R.sup.2=H], [1446; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1447; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1448; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1449; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1450; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1451; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=F, R.sup.12=H], [1452; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, R.sup.3=H, R.sup.1=F, R.sup.12=H], [1453; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, R.sup.3=H, R.sup.11=F, R.sup.12=H], [1454; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, R.sup.3=H, R.sup.11=F, R.sup.12=H], [1455; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, R.sup.3=H, R.sup.11=F, R.sup.12=H], [1456; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, R.sup.3=H, R.sup.11=F, R.sup.12=H], [1457; Q=Q.sup.q12, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, R.sup.3=H, R.sup.11=F, R.sup.12=H], [1458; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1459; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1460; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1461; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1462; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1463; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1464; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1465; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=Br, R.sup.12=H], [1466; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, R.sup.3=H, R.sup.11=Br, R.sup.12=H], [1467; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, R.sup.3=H, R.sup.11=Br, R.sup.12=H], [1468; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, R.sup.3=H, R.sup.11=Br, R.sup.12=H], [1469; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, R.sup.3=H, R.sup.11=Br, R.sup.12=H], [1470; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, R.sup.3=H, R.sup.11=Br, R.sup.12=H], [1471; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, R.sup.3=H, R.sup.11=Br, R.sup.12=H], [1472; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1473; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1474; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1475; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, R.sup.3=H, R.sup.11=Me, R.sup.12=H][1476; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1477; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1478; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1479; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1480; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1481; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1482; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1483; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1484; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1485; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1486; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1487; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1488; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1489; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1490; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1491; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1492; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1493; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=OCF.sub.3, R.sup.12=H], [1494; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, R.sup.3=H, R.sup.11=OCF.sub.3, R.sup.12=H], [1495; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, R.sup.3=H, R.sup.11=OCF.sub.3, R.sup.12=H], [1496; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, R.sup.3=H, R.sup.11=OCF.sub.3, R.sup.12=H], [1497; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, R.sup.3=H, R.sup.11=OCF.sub.3, R.sup.12=H], [1498; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, R.sup.3=H, R.sup.11=OCF.sub.3, R.sup.12=H], [1499; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, R.sup.3=H, R.sup.11=OCF.sub.3, R.sup.12=H], [1500; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], [1501; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], [1502; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], [1503; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], [1504; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], [1505; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], [1506; Q=Q.sup.q2, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], [1507; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1508; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1509; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1510; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1511; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1512; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1513; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1514; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1515; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1516; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1517; Q=Q.sup.v3, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1518; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1519; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1520; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1521; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1522; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1523; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1524; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1525; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1526; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1527; Q=Q.sup.q13, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1528; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=Br, R.sup.11=H, R.sup.12=H], [1529; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, R.sup.3=Br, R.sup.11=H, R.sup.12=H], [1530; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, R.sup.3=Br, R.sup.11=H, R.sup.12=H], [1531; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, R.sup.3=Br, R.sup.11=H, R.sup.12=H], [1532; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, R.sup.3=Br, R.sup.11=H, R.sup.12=H], [1533; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, R.sup.3=Br, R.sup.11=H, R.sup.12=H], [1534; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, R.sup.3=Br, R.sup.11=H, R.sup.12=H], [1535; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1536; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1537; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1538; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1539; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1540; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1541; Q=Q.sup.q13, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, R.sup.3=Me, R.sup.11=H, R.sup.12=H][1542; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1543; Q=Q.sup.p3, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1544; Q=Q.sup.q13, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1545; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1546; Q=Q.sup.q13, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1547; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1548; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1549; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1550; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1551; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1552; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1553; Q=Q.sup.q13, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=C %, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1554; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1555; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1556; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=OCF.sub.3, R.sup.11=H, R.sup.12=H], [1557; Q=Q.sup.q13, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, R.sup.3=OCF.sub.3, R.sup.11=H, R.sup.12=H], [1558; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.1=F, R.sup.3=OCF.sub.3, R.sup.11=H, R.sup.12=H], [1559; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, R.sup.3=OCF.sub.3, R.sup.11=H, R.sup.12=H], [1560; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, R.sup.3=OCF.sub.3, R.sup.11=H, R.sup.12=H], [1561; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, R.sup.3=OCF.sub.3, R.sup.11=H, R.sup.12=H], [1562; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, R.sup.3=OCF.sub.3, R.sup.11=H, R.sup.12=H], [1563; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1564; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1565; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1566; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1567; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1568; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1569; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1570; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=F, R.sup.12=H], [1571; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, R.sup.3=H, R.sup.11=F, R.sup.12=H], [1572; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, R.sup.3=H, R.sup.11=F, R.sup.12=H], [1573; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, R.sup.3=H, R.sup.1=F, R.sup.12=H], [1574; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, R.sup.3=H, R.sup.11=F, R.sup.12=H], [1575; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, R.sup.3=H, R.sup.11=F, R.sup.12=H], [1576; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, R.sup.3=H, R.sup.11=F, R.sup.2=H], [1577; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1578; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1579; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1580; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1581; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1582; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1583; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1584; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=Br, R.sup.12=H], [1585; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, R.sup.3=H, R.sup.11=Br, R.sup.12=H], [1586; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, R.sup.3=H, R.sup.11=Br, R.sup.12=H], [1587; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, R.sup.3=H, R.sup.11=Br, R.sup.12=H], [1588; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, R.sup.3=H, R.sup.11=Br, R.sup.12=H], [1589; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, R.sup.3=H, R.sup.11=Br, R.sup.12=H], [1590; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, R.sup.3=H, R.sup.11=Br, R.sup.12=H], [1591; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1592; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1593; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1594; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1595; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1596; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, R.sup.3=H, R.sup.11=Me, R.sup.12=H][1597; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, R.sup.3=H, R=Me, R.sup.12=H], [1598; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1599; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1600; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1601; Q=Q.sup.q13, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1602; Q=Q.sup.q13, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1603; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1604; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1605; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1606; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1607; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1608; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1609; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1610; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1611; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1612; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=OCF.sub.3, R.sup.12=H], [1613; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, R.sup.3=H, R.sup.11=OCF.sub.3, R.sup.12=H], [1614; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, R.sup.3=H, R.sup.11=OCF.sub.3, R.sup.12=H], [1615; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, R.sup.3=H, R.sup.11=OCF.sub.3, R.sup.12=H], [1616; Q=Q.sup.p3, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, R.sup.3=H, R.sup.11=OCF.sub.3, R.sup.12=H], [1617; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, R.sup.3=H, R.sup.11=OCF.sub.3, R.sup.12=H], [1618; Q=Q.sup.q13, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, R.sup.3=H, R.sup.11=OCF.sub.3, R.sup.12=H], [1619; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], [1620; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], [1621; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], [1622; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], [1623; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], [1624; Q=Q.sup.q3, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], [1625; Q=Q.sup.q13, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], [1626; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.7=Me, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1627; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, A.sup.7=Me, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1628; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, A.sup.7=Me, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1629; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, A.sup.7=Me, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1630; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, A.sup.7=Me, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1631; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, A.sup.7=Me, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1632; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, A.sup.7=Me, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1633; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.7=Et, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1634; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, A.sup.7=Et, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1635; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, A.sup.7=Et, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1636; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, A.sup.7=Et, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1637; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, A.sup.7=Et, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1638; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, A.sup.7=Et, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1639; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, A.sup.7=Et, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1640; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.7=cyclopropyl, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1641; Q=Q.sup.q1, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, A.sup.7=cyclopropyl, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1642; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, A.sup.7=cyclopropyl, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1643; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, A.sup.7=cyclopropyl, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1644; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, A.sup.7=cyclopropyl, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1645; Q=Q.sup.4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, A.sup.7=cyclopropyl, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1646; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, A.sup.7=cyclopropyl, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1647; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.7=Me, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1648; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, A.sup.7=Me, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1649; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, A.sup.7=Me, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1650; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, A.sup.7=Me, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1651; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, A.sup.7=Me, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1652; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, A.sup.7=Me, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1653; Q=Q.sup.q5, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, A.sup.7=Me, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1654; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.7=Et, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1655; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, A.sup.7=Et, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1656; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, A.sup.7=Et, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1657; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, A.sup.7=Et, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1658; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=C, A.sup.4=Cl, A.sup.7=Et, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1659; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, A.sup.7=Et, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1660; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, A.sup.7=Et, R.sup.3=F, R.sup.11=H, R.sup.12=H], [1661; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.7=Me, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1662; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, A.sup.7=Me, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1663; Q=Q.sup.q4, A.sup.1H, A.sup.2=H, A.sup.3=F, A.sup.4=F, A.sup.7=Me, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1664; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, A.sup.7=Me, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1665; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, A.sup.7=Me, R.sup.3=C, R.sup.11=H, R.sup.12=H], [1666; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, A.sup.7=Me, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1667; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, A.sup.7=Me, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1668; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.7=Et, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1669; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, A.sup.7=Et, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1670; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, A.sup.7=Et, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1671; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, A.sup.7=Et, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1672; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, A.sup.7=Et, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1673; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, A.sup.7=Et, R.sup.3=Cl, R.sup.11=H, R.sup.2=H], [1674; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, A.sup.7=Et, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1675; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.7=Me, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1676; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, A.sup.7=Me, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1677; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, A.sup.7=Me, R=Me, R.sup.11=H, R.sup.12=H], [1678; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, A.sup.7=Me, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1679; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=C, A.sup.4=Cl, A.sup.7=Me, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1680; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, A.sup.7=Me, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1681; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, A.sup.7=Me, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1682; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.7=Et, R=Me, R.sup.11=H, R.sup.12=H], [1683; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, A.sup.7=Et, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1684; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, A.sup.7=Et, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1685; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, A.sup.7=Et, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1686; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, A.sup.7=Et, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1687; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, A.sup.7=Et, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1688; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, A.sup.7=Et, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1689; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.7=Me, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1690; Q=Q.sup.q4, A.sup.2=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, A.sup.7=Me, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1691; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, A.sup.7=Me, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1692; Q=Q.sup.q4, A.sup.5=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, A.sup.7=Me, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1693; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, A.sup.7=Me, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1694; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, A.sup.7=Me, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1695; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, A.sup.7=Me, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1696; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.7=Et, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1697; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, A.sup.7=Et, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1698; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.1=F, A.sup.7=Et, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1699; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, A.sup.7=Et, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1700; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, A.sup.7=Et, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1701; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, A.sup.7=Et, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1702; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, A.sup.7=Et, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1703; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.7=Me, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1704; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, A.sup.7=Me, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1705; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, A.sup.7=Me, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1706; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, A.sup.7=Me, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1707; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, A.sup.7=Me, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1708; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, A.sup.7=Me, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1709; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, A.sup.7=Me, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1710; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.7=Et, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1711; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, A.sup.7=Et, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1712; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, A.sup.7=Et, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1713; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, A.sup.7=Et, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1714; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, A.sup.7=Et, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1715; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, A.sup.7=Et, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1716; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, A.sup.7=Et, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1717; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.7=Me, R.sup.3=H, R.sup.11=F, R.sup.12=H], [1718; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, A.sup.7=Me, R.sup.3=H, R.sup.1=F, R.sup.12=H], [1719; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, A.sup.7=Me, R.sup.3=H, R.sup.11=F, R.sup.12=H], [1720; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=C, A.sup.4=H, A.sup.7=Me, R.sup.3=H, R.sup.11=F, R.sup.12=H], [1721; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, A.sup.7=Me, R.sup.3=H, R.sup.11=F, R.sup.12=H], [1722; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, A.sup.7=Me, R.sup.3=H, R.sup.11=F, R.sup.12=H], [1723; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, A.sup.7=Me, R.sup.3=H, R.sup.11=F, R.sup.12=H], [1724; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.7=Et, R.sup.3=H, R.sup.11=F, R.sup.12=H], [1725; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, A.sup.7=Et, R.sup.3=H, R.sup.11=F, R.sup.12=H], [1726; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, A.sup.7=Et, R.sup.3=H, R.sup.11=F, R.sup.12=H], [1727; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, A.sup.7=Et, R.sup.3=H, R.sup.11=F, R.sup.12=H], [1728; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, A.sup.7=Et, R.sup.3=H, R.sup.11=F, R.sup.12=H], [1729; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, A.sup.7=Et, R.sup.3=H, R.sup.1=F, R.sup.12=H], [1730; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, A.sup.7=Et, R.sup.3=H, R.sup.11=F, R.sup.12=H], [1731; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.7=Me, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1732; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, A.sup.7=Me, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1733; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, A.sup.7=Me, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1734; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, A.sup.7=Me, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1735; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, A.sup.7=Me, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1736; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, A.sup.7=Me, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1737; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, A.sup.7=Me, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1738; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.7=Et, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1739; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, A.sup.7=Et, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1740; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, A.sup.7=Et, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1741; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, A.sup.7=Et, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1742; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, A.sup.7=Et, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1743; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, A.sup.7=Et, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1744; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, A.sup.7=Et, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1745; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.7=Me, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1746; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, A.sup.7=Me, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1747; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, A.sup.7=Me, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1748; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, A.sup.7=Me, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1749; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, A.sup.7=Me, R.sup.3=H, R.sup.11=Me, R.sup.2=H], [1750; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, A.sup.7=Me, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1751; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.3=Me, A.sup.7=Me, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1752; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.7=Et, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1753; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, A.sup.7=Et, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1754; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, A.sup.7=Et, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1755; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.1=H, A.sup.7=Et, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1756; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, A.sup.7=Et, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1757; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, A.sup.7=Et, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1758; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, A.sup.7=Et, R.sup.3=H, R.sup.11=Me, R.sup.12=H], [1759; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.7=Me, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1760; Q=Q.sup.q4, A.sup.5=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, A.sup.7=Me, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1761; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.5=F, A.sup.7=Me, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1762; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, A.sup.7=Me, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1763; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, A.sup.7=Me, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1764; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, A.sup.7=Me, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1765; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, A.sup.7=Me, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1766; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.7=Et, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1767; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, A.sup.7=Et, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1768; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, A.sup.7=Et, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1769; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, A.sup.7=Et, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1770; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, A.sup.7=Et, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1771; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, A.sup.7=Et, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1772; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, A.sup.7=Et, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1773; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.7=Me, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1774; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, A.sup.7=Me, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1775; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, A.sup.1=Me, R.sup.3=H, R.sup.11=OMe, R.sup.12=H][1776; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, A.sup.7=Me, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1777; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, A.sup.7=Me, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1778; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, A.sup.7=Me, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1779; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, A.sup.7=Me, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1780; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, A.sup.7=Et, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1781; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=H, A.sup.7=Et, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1782; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=F, A.sup.4=F, A.sup.7=Et, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1783; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=H, A.sup.7=Et, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1784; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.4=Cl, A.sup.7=Et, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1785; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=H, A.sup.7=Et, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1786; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Me, A.sup.4=Me, A.sup.7=Et, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1787; Q=Q.sup.q5, A.sup.1=H, A.sup.2=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1788; Q=Q.sup.q5, A.sup.1=H, A.sup.2=H, A.sup.5=F, A.sup.6=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1789; Q=Q.sup.q5, A.sup.1=H, A.sup.2=H, A.sup.5=F, A.sup.6=F, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1790; Q=Q.sup.q5, A.sup.1=H, A.sup.2=H, A.sup.5=Cl, A.sup.6=Cl, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1791; Q=Q.sup.q5, A.sup.1=H, A.sup.2=H, A.sup.5=Me, A.sup.6=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1792; Q=Q.sup.q5, A.sup.1=H, A.sup.2=H, A.sup.5=Me, A.sup.6=Me, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1793; Q=Q.sup.q5, A.sup.1=H, A.sup.2=H, A.sup.5=H, A.sup.6=H, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1794; Q=Q.sup.q5, A.sup.1=H, A.sup.2=H, A.sup.5=F, A.sup.6=H, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1795; Q=Q.sup.q5, A.sup.3=H, A.sup.2=H, A.sup.5=F, A.sup.6=F, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1796; Q=Q.sup.q5, A.sup.1=H, A.sup.2=H, A.sup.5=Cl, A.sup.6=Cl, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1797; Q=Q.sup.q5, A.sup.1=H, A.sup.2=H, A.sup.5=Me, A.sup.6=H, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1798; Q=Q.sup.q59, A.sup.1=H, A.sup.2=H, A.sup.5=Me, A.sup.6=Me, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1799; Q=Q.sup.q45, A.sup.1=H, A.sup.2=H, A.sup.1=H, A.sup.1=H, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1800; Q=Q.sup.q5, A.sup.1=H, A.sup.2=H, A.sup.5=F, A.sup.6=H, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1801; Q=Q.sup.q5, A.sup.1=H, A.sup.2=H, A.sup.5=F, A.sup.6=F, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1802; Q=Q.sup.q5, A.sup.1=H, A.sup.2=H, A.sup.5=Cl, A.sup.6=Cl, R.sup.3=OMe, R.sup.11=H, R.sup.12=H][1803; Q=Q.sup.q5, A.sup.1=H, A.sup.2=H, A.sup.5=Me, A.sup.6=H, R.sup.3=Me, R.sup.11=H, R.sup.12=H], [1804; Q=Q.sup.q5, A.sup.1=H, A.sup.2=H, A.sup.5=Me, A.sup.6=Me, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1805; Q=Q.sup.q5, A.sup.1=H, A.sup.2=H, A.sup.5=H, A.sup.6=H, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1806; Q=Q.sup.q5, A.sup.1=H, A.sup.2=H, A.sup.2=F, A.sup.6=H, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1807; Q=Q.sup.q5, A.sup.1=H, A.sup.2=H, A.sup.5=F, A.sup.6=F, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1808; Q=Q.sup.q5, A.sup.1=H, A.sup.2=H, A.sup.5=Cl, A.sup.6=Cl, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1809; Q=Q.sup.q5, A.sup.1=H, A.sup.2=H, A.sup.5=Me, A.sup.6=H, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1810; Q=Q.sup.q5, A.sup.1=H, A.sup.2=H, A.sup.5=Me, A.sup.6=Me, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1811; Q=Q.sup.q5, A.sup.1=H, A.sup.2=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1812; Q=Q.sup.q5, A.sup.1=H, A.sup.2=H, A.sup.5=F, A.sup.6=H, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1813; Q=Q.sup.q5, A.sup.1=H, A.sup.2=H, A.sup.5=F, A.sup.6=F, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1814; Q=Q.sup.q5, A.sup.1=H, A.sup.2=H, A.sup.5=Cl, A.sup.6=Cl, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1815; Q=Q.sup.q5, A.sup.1=H, A.sup.2=H, A.sup.5=Me, A.sup.6=H, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1816; Q=Q.sup.q5, A.sup.1=H, A.sup.2=H, A.sup.5=Me, A.sup.6=Me, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1817; Q=Q.sup.q5, A.sup.1=H, A.sup.2=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1818; Q=Q.sup.q5, A.sup.1=H, A.sup.2=H, A.sup.5=F, A.sup.6=H, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1819; Q=Q.sup.q5, A.sup.1=H, A.sup.2=H, A.sup.5=F, A.sup.6=F, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1820; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.6=Cl, R.sup.3=H, R=n=OMe, R.sup.12=H], [1821; Q=Q.sup.q5, A.sup.1=H, A.sup.2=H, A.sup.5=Me, A.sup.6=H, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1822; Q=Q.sup.q5, A.sup.1=H, A.sup.2=H, A.sup.5=Me, A.sup.6=Me, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1823; Q=Q, A.sup.1=H, A.sup.2=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1824; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.5=F, A.sup.6=H, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1825; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.5=F, A.sup.6=F, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1826; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=Cl, A.sup.6=Cl, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1827; Q=Q.sup.q5, A.sup.1=H, A.sup.2=H, A.sup.5=Me, A.sup.6=H, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1828; Q=Q.sup.q5, A.sup.1=H, A.sup.2=H, A.sup.5=Me, A.sup.6=Me, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1829; Q=Q.sup.q6, A.sup.1=H, A.sup.2=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1830; Q=Q.sup.q6, A.sup.1=H, A.sup.2=H, A.sup.5=F, A.sup.6=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1831; Q=Q.sup.q6, A.sup.1=H, A.sup.2=H, A.sup.5=F, A.sup.6=F, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1832; Q=Q.sup.q6, A.sup.1=H, A.sup.2=H, A.sup.5=Cl, A.sup.6=Cl, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1833; Q=Q.sup.q6, A.sup.1=H, A.sup.2=H, A.sup.5=Me, A.sup.6=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1834; Q=Q.sup.q6, A.sup.1=H, A.sup.2=H, A.sup.5=Me, A.sup.6=Me, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1835; Q=Q.sup.q6, A.sup.1=H, A.sup.2=H, A.sup.5=H, A.sup.6=H, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1836; Q=Q.sup.q6, A.sup.1=H, A.sup.2=H, A.sup.5=F, A.sup.6=H, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1837; Q=Q.sup.q6, A.sup.1=H, A.sup.2=H, A.sup.5=F, A.sup.6=F, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1838; Q=Q.sup.q6, A.sup.1=H, A.sup.2=H, A.sup.5=Cl, A.sup.6=Cl, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1839; Q=Q.sup.q6, A.sup.1=H, A.sup.2=H, A.sup.5=Me, A.sup.6=H, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1840; Q=Q.sup.q6, A.sup.1=H, A.sup.2=H, A.sup.5=Me, A.sup.6=Me, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1841; Q=Q.sup.q6, A.sup.1=H, A.sup.2=H, A.sup.5=H, A.sup.6=H, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1842; Q=Q.sup.q6, A.sup.1=H, A.sup.2=H, A.sup.5=F, A.sup.6=H, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1843; Q=Q.sup.q6, A.sup.1=H, A.sup.2=H, A.sup.5=F, A.sup.6=F, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1844; Q=Q.sup.q6, A.sup.1=H, A.sup.2=H, A.sup.5=Cl, A.sup.6=Cl, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1845; Q=Q.sup.q6, A.sup.1=H, A.sup.2=H, A.sup.5=Me, A.sup.6=H, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1846; Q=Q.sup.q6, A.sup.1=H, A.sup.2=H, A.sup.5=Me, A.sup.6=Me, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1847; Q=Q.sup.q6, A.sup.1=H, A.sup.2=H, A.sup.5=H, A.sup.6=H, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1848; Q=Q.sup.q6, A.sup.1=H, A.sup.2=H, A.sup.5=F, A.sup.6=H, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1849; Q=Q.sup.q6, A.sup.1=H, A.sup.2=H, A.sup.5=F, A.sup.6=F, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1850; Q=Q.sup.q6, A.sup.1=H, A.sup.2=H, A.sup.5=Cl, A.sup.6=Cl, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1851; Q=Q.sup.q6, A.sup.1=H, A.sup.2=H, A.sup.5=Me, A.sup.6=H, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1852; Q=Q.sup.q6, A.sup.1=H, A.sup.2=H, A.sup.5=Me, A.sup.6=Me, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1853; Q=Q.sup.q6, A.sup.1=H, A.sup.2=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1854; Q=Q.sup.q6, A.sup.1=H, A.sup.2=H, A.sup.5=F, A.sup.6=H, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1855; Q=Q.sup.q6, A.sup.1=H, A.sup.2=H, A.sup.5=F, A.sup.6=F, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1856; Q=Q.sup.q6, A.sup.1=H, A.sup.2=H, A.sup.5=Cl, A.sup.6=Cl, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1857; Q=Q.sup.q6, A.sup.1=H, A.sup.2=H, A.sup.5=Me, A.sup.6=H, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1858; Q=Q.sup.q6, A.sup.1=H, A.sup.2=H, A.sup.5=Me, A.sup.6=Me, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1859; Q=Q.sup.q6, A.sup.1=H, A.sup.2=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1860; Q=Q.sup.q6, A.sup.1=H, A.sup.2=H, A.sup.5=F, A.sup.6=H, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1861; Q=Q.sup.q6, A.sup.1=H, A.sup.2=H, A.sup.5=F, A.sup.6=F, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1862; Q=Q.sup.q6, A.sup.1=H, A.sup.2=H, A.sup.5=Cl, A.sup.6=Cl, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1863; Q=Q.sup.q6, A.sup.1=H, A.sup.2=H, A.sup.5=Me, A.sup.6=H, R.sup.3=H, R.sup.11=OMe, R.sup.2=H], [1864; Q=Q.sup.q6, A.sup.1=H, A.sup.2=H, A.sup.5=Me, A.sup.6=Me, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1865; Q=Q.sup.q6, A.sup.1=H, A.sup.2=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1866; Q=Q.sup.q6, A.sup.1=H, A.sup.2=H, A.sup.5=F, A.sup.6=H, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1867; Q=Q.sup.q6, A.sup.1=H, A.sup.2=H, A.sup.5=F, A.sup.6=F, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1868; Q=Q.sup.q6, A.sup.1=H, A.sup.2=H, A.sup.5=Cl, A.sup.6=Cl, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1869; Q=Q.sup.q6, A.sup.1=H, A.sup.2=H, A.sup.5=Me, A.sup.6=H, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1870; Q=Q.sup.q6, A.sup.1=H, A.sup.2=H, A.sup.5=Me, A.sup.6=Me, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1871; Q=Q.sup.q7, A.sup.1=H, A.sup.2=H, A.sup.5=H, A.sup.6=H, A.sup.8=Me, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1872; Q=Q.sup.q7, A.sup.1=H, A.sup.2=H, A.sup.5=Me, A.sup.6=H, A.sup.8=Me, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1873; Q=Q.sup.q7, A.sup.1=H, A.sup.2=H, A.sup.5=Me, A.sup.6=Me, A.sup.8=Me, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1874; Q=Q.sup.q7, A.sup.1=H, A.sup.2=H, A.sup.5=H, A.sup.6=H, A.sup.8=Me, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1875; Q=Q.sup.q7, A.sup.1=H, A.sup.2=H, A.sup.5=Me, A.sup.6=H, A.sup.8=Me, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1876; Q=Q.sup.q7, A.sup.1=H, A.sup.2=H, A.sup.5=Me, A.sup.6=Me, A.sup.8=Me, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1877; Q=Q.sup.q7, A.sup.1=H, A.sup.2=H, A.sup.5=H, A.sup.6=H, A.sup.8=Me, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1878; Q=Q.sup.q7, A.sup.1=H, A.sup.2=H, A.sup.5=Me, A.sup.6=H, A.sup.1=Me, R.sup.3=OMe, R.sup.11=H, R.sup.12=H][1879; Q=Q.sup.q7, A.sup.1=H, A.sup.2=H, A.sup.5=Me, A.sup.6=Me, A.sup.8=Me, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1880; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.5=H, A.sup.6=H, A.sup.8=Me, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1881; Q=Q.sup.q7, A.sup.1=H, A.sup.2=H, A.sup.5=Me, A.sup.6=H, A.sup.8=Me, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1882; Q=Q.sup.q7, A.sup.1=H, A.sup.2=H, A.sup.5=Me, A.sup.6=Me, A.sup.8=Me, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1883; Q=Q.sup.q8, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1884; Q=Q.sup.q5, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1885; Q=Q.sup.q8, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1886; Q=Q.sup.q5, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1887; Q=Q.sup.q8, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=OCF.sub.3, R.sup.11=H, R.sup.12=H], [1888; Q=Q.sup.q8, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1889; Q=Q.sup.q8, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1890; Q=Q.sup.q5, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1891; Q=Q.sup.q8, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1892; Q=Q.sup.q4, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=OCF.sub.3, R.sup.12=H], [1893; Q=Q.sup.q9, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], [1894; Q=Q.sup.q9, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1895; Q=Q.sup.q9, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1896; Q=Q.sup.q9, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1897; Q=Q.sup.q9, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1898; Q=Q.sup.q9, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=OCF.sub.3, R.sup.11=H, R.sup.12=H], [1899; Q=Q.sup.q9, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1900; Q=Q.sup.q9, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1901; Q=Q.sup.q9, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1902; Q=Q.sup.q9, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1903; Q=Q.sup.q9, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=OCF.sub.3, R.sup.12=H], [1904; Q=Q.sup.q9, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], [1905; Q=Q.sup.q10, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1906; Q=Q.sup.q10, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1907; Q=Q.sup.q10, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H][1908; Q=Q.sup.q10, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1909; Q=Q.sup.q10, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=OCF.sub.3, R.sup.11=H, R.sup.12=H], [1910; Q=Q.sup.q10, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1911; Q=Q.sup.q10, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1912; Q=Q.sup.10, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1913; Q=Q.sup.q10, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1914; Q=Q.sup.q10, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=OCF.sub.3, R.sup.12=H], [1915; Q=Q.sup.q10, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], [1916; Q=Q.sup.q10, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1917; Q=Q.sup.q9, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1918; Q=Q.sup.q11, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1919; Q=Q.sup.q11, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1920; Q=Q.sup.q11, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=OCF.sub.3, R.sup.11=H, R.sup.12=H], [1921; Q=Q.sup.q11, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1922; Q=Q.sup.q11, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1923; Q=Q.sup.q11, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1924; Q=Q.sup.q11, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1925; Q=Q.sup.q11, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.1=H, R.sup.3=H, R.sup.11=OCF.sub.3, R.sup.12=H], [1926; Q=Q.sup.q11, A.sup.1=H, A.sup.2=H, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], [1927; Q=Q.sup.q12, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1928; Q=Q.sup.q12, A.sup.3=F, A.sup.4=F, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1929; Q=Q.sup.q12, A.sup.3=Cl, A.sup.4=Cl, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1930; Q=Q.sup.q12, A.sup.3=Me, A.sup.4=Me, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1931; Q=Q.sup.q2, A.sup.3=H, A.sup.4=H, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1932; Q=Q.sup.q12, A.sup.3=F, A.sup.4=F, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1933; Q=Q.sup.q12, A.sup.3=Cl, A.sup.4=Cl, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1934; Q=Q.sup.q12, A.sup.3=Me, A.sup.4=Me, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1935; Q=Q.sup.q12, A.sup.3=H, A.sup.4=H, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1936; Q=Q.sup.q12, A.sup.3=F, A.sup.4=F, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1937; Q=Q.sup.q12, A.sup.3=Cl, A.sup.4=Cl, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1938; Q=Q.sup.q12, A.sup.3=Me, A.sup.7=Me, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1939; Q=Q.sup.q12, A.sup.3=H, A.sup.4=H, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1940; Q=Q.sup.q12, A.sup.3=F, A.sup.4=F, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1941; Q=Q.sup.q12, A.sup.3=C, A.sup.4=Cl, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1942; Q=Q.sup.q12, A.sup.3=Me, A.sup.4=Me, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1943; Q=Q.sup.q12, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1944; Q=Q.sup.q12, A.sup.3=F, A.sup.4=F, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1945; Q=Q.sup.q12, A.sup.3=Cl, A.sup.4=Cl, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1946; Q=Q.sup.q12, A.sup.3=Me, A.sup.4=Me, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1947; Q=Q.sup.q12, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1948; Q=Q.sup.q12, A.sup.3=F, A.sup.4=F, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1949; Q=Q.sup.q12, A.sup.3=Cl, A.sup.4=Cl, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1950; Q=Q.sup.q12, A.sup.3=Me, A.sup.7=Me, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1951; Q=Q.sup.q12, A.sup.3=H, A.sup.4=H, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1952; Q=Q.sup.q2, A.sup.3=F, A.sup.4=F, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1953; Q=Q.sup.q12, A.sup.3=Cl, A.sup.4=Cl, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1954; Q=Q.sup.q12, A.sup.3=Me, A.sup.4=Me, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1955; Q=Q.sup.q13, A.sup.1=H, A.sup.2=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1956; Q=Q.sup.q14, A.sup.1=H, A.sup.2=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1957; Q=Q.sup.q15, A.sup.1=H, A.sup.2=H, A.sup.7=Me, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1958; Q=Q.sup.q16, A.sup.1=H, A.sup.2=H, A.sup.8=Me, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1959; Q=Q.sup.q17, A.sup.1=H, A.sup.2=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1960; Q=Q.sup.q18, A.sup.1=H, A.sup.2=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1961; Q=Q.sup.q19, A.sup.1=H, A.sup.2=H, A.sup.8=Me, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1962; Q=Q.sup.q20, A.sup.1=H, A.sup.2=H, A.sup.8=Me, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1963; Q=Q.sup.q21, A.sup.1=H, A.sup.3=H, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1964; Q=Q.sup.q21, A.sup.1=H, A.sup.3=Me, A.sup.5=H, A.sup.6=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1965; Q=Q.sup.q21, A.sup.1=H, A.sup.3=H, A.sup.5=F, A.sup.6=F, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1966; Q=Q.sup.q21, A.sup.1=H, A.sup.3=Me, A.sup.5=F, A.sup.6=F, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1967; Q=Q.sup.q21, A.sup.1=H, A.sup.3=H, A.sup.5=H, A.sup.6=H, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1968; Q=Q.sup.q21, A.sup.1=H, A.sup.3=Me, A.sup.5=H, A.sup.6=H, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1969; Q=Q.sup.q21, A.sup.1=H, A.sup.3=H, A.sup.5=F, A.sup.6=F, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1970; Q=Q.sup.q21, A.sup.1=H, A.sup.3=Me, A.sup.5=F, A.sup.6=F, R.sup.3=C, R.sup.11=H, R.sup.12=H], [1971; Q=Q.sup.q21, A.sup.1=H, A.sup.3=H, A.sup.5=H, A.sup.6=H, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1972; Q=Q.sup.q21, A.sup.1=H, A.sup.3=Me, A.sup.5=H, A.sup.6=H, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1973; Q=Q.sup.q21, A.sup.1=H, A.sup.3=H, A.sup.5=F, A.sup.6=F, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1974; Q=Q.sup.q21, A.sup.1=H, A.sup.3=Me, A.sup.5=F, A.sup.6=F, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1975; Q=Q.sup.q21, A.sup.1=H, A.sup.3=H, A.sup.5=H, A.sup.6=H, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1976; Q=Q.sup.q21, A.sup.1=H, A.sup.3=Me, A.sup.5=H, A.sup.6=H, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1977; Q=Q.sup.q21, A.sup.1=H, A.sup.3=H, A.sup.5=F, A.sup.6=F, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1978; Q=Q.sup.q21, A.sup.1=H, A.sup.3=Me, A.sup.5=F, A.sup.6=F, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1979; Q=Q.sup.q21, A.sup.1=H, A.sup.3=H, A.sup.5=H, A.sup.6=H, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1980; Q=Q.sup.q21, A.sup.1=H, A.sup.3=Me, A.sup.5=H, A.sup.6=H, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1981; Q=Q.sup.q21, A.sup.1=H, A.sup.3=H, A.sup.5=F, A.sup.6=F, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1982; Q=Q.sup.q21, A.sup.1=H, A.sup.3=Me, A.sup.5=F, A.sup.6=F, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1983; Q=Q.sup.q22, A.sup.1=H, A.sup.3=H, A.sup.7=Me, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1984; Q=Q.sup.q22, A.sup.1=H, A.sup.3=Me, A.sup.7=Me, R.sup.3=H, R.sup.11=H, R.sup.12=H], [1985; Q=Q.sup.q22, A.sup.1=H, A.sup.3=H, A.sup.7=Me, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1986; Q=Q.sup.q22, A.sup.1=H, A.sup.3=Me, A.sup.7=Me, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [1987; Q=Q.sup.q22, A.sup.1=H, A.sup.3=H, A.sup.7=Me, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1988; Q=Q.sup.q22, A.sup.1=H, A.sup.3=Me, A.sup.7=Me, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [1989; Q=Q.sup.q22, A.sup.1=H, A.sup.3=H, A.sup.7=Me, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1990; Q=Q.sup.q22, A.sup.1=H, A.sup.3=Me, A.sup.7=Me, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [1991; Q=Q.sup.q22, A.sup.1=H, A.sup.3=H, A.sup.7=Me, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1992; Q=Q.sup.q22, A.sup.1=H, A.sup.3=Me, A.sup.7=Me, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [1993; Q=Q.sup.q22, A.sup.1=H, A.sup.3=H, A.sup.7=Me, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1994; Q=Q.sup.q22, A.sup.1=H, A.sup.3=Me, A.sup.7=Me, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [1995; Q=Q.sup.q22, A.sup.1=H, A.sup.3=H, A.sup.7=Me, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1996; Q=Q.sup.q22, A.sup.1=H, A.sup.3=Me, A.sup.7=Me, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [1997; Q=Q.sup.q22, A.sup.1=H, A.sup.3=H, A.sup.7=Me, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1998; Q=Q.sup.q22, A.sup.1=H, A.sup.3=Me, A.sup.7=Me, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [1999; Q=Q.sup.q22, A.sup.1=H, A.sup.3=H, A.sup.7=Me, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], [2000; Q=Q.sup.q22, A.sup.1=H, A.sup.3=Me, A.sup.7=Me, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], [2001; Q=Q.sup.q23, A.sup.1=H, R.sup.3=H, R.sup.11=H, R.sup.12=H], [2002; Q=Q.sup.q23, A.sup.1=H, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [2003; Q=Q.sup.q23, A.sup.1=H, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [2004; Q=Q.sup.q23, A.sup.1=H, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [2005; Q=Q.sup.q23, A.sup.1=H, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [2006; Q=Q.sup.q23, A.sup.1=H, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [2007; Q=Q.sup.q23, A.sup.1=H, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [2008; Q=Q.sup.q23, A.sup.1=H, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [2009; Q=Q.sup.q23, A.sup.1=H, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], [2010; Q=Q.sup.q24, A.sup.1=H, A.sup.7=Me, R.sup.3=H, R.sup.11=H, R.sup.12=H], [2011; Q=Q.sup.q24, A.sup.1=H, A.sup.7=Me, R.sup.3=Cl, R.sup.11=H, R.sup.12=H], [2012; Q=Q.sup.q24, A.sup.1=H, A.sup.7=Me, R.sup.3=OMe, R.sup.11=H, R.sup.12=H], [2013; Q=Q.sup.q24, A.sup.1=H, A.sup.7=Me, R.sup.3=CF.sub.3, R.sup.11=H, R.sup.12=H], [2014; Q=Q.sup.q24, A.sup.1=H, A.sup.7=Me, R.sup.3=SMe, R.sup.11=H, R.sup.12=H], [2015; Q=Q.sup.q24, A.sup.1=H, A.sup.7=Me, R.sup.3=H, R.sup.11=Cl, R.sup.12=H], [2016; Q=Q.sup.q24, A.sup.1=H, A.sup.7=Me, R.sup.3=H, R.sup.11=OMe, R.sup.12=H], [2017; Q=Q.sup.q24, A.sup.1=H, A.sup.7=Me, R.sup.3=H, R.sup.11=CF.sub.3, R.sup.12=H], [2018; Q=Q.sup.q24, A.sup.1=H, A.sup.7=Me, R.sup.3=H, R.sup.11=SMe, R.sup.12=H], 2019; Q=Q.sup.r1, A.sup.9=H, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2020; Q=Q.sup.r1, A.sup.9=F, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2021; Q=Q.sup.r1, A.sup.9=H, A.sup.10=F, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2022; Q=Q.sup.r1, A.sup.9=H, A.sup.10=H, A.sup.11=F, A.sup.12=H, A.sup.13=H], [2023; Q=Q.sup.r1, A.sup.9=F, A.sup.10=F, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2024; Q=Q.sup.r1, A.sup.9=F, A.sup.10=H, A.sup.11=F, A.sup.12=H, A.sup.13=H], [2025; Q=Q.sup.q11, A.sup.9=F, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=F], [2026; Q=Q.sup.r1, A.sup.9=H, A.sup.10=F, A.sup.11=F, A.sup.12=H, A.sup.13=H], [2027; Q=Q.sup.r1, A.sup.9=H, A.sup.10=F, A.sup.11=H, A.sup.12=F, A.sup.13=H], [2028; Q=Q.sup.r1, A.sup.9=Cl, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2029; Q=Q.sup.r1, A.sup.9=H, A.sup.10=Cl, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2030; Q=Q.sup.r1, A.sup.9=H, A.sup.10=H, A.sup.11=Cl, A.sup.12=H, A.sup.13=H], [2031; Q=Q.sup.r1, A.sup.9=Cl, A.sup.10=Cl, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2032; Q=Q.sup.r1, A.sup.9=Cl, A.sup.10=H, A.sup.11=Cl, A.sup.12=H, A.sup.13=H], [2033; Q=Q.sup.r1, A.sup.9=Cl, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=Cl], [2034; Q=Q.sup.r1, A.sup.9=H, A.sup.10=Cl, A.sup.11=Cl, A.sup.12=H, A.sup.13=H], [2035; Q=Q.sup.r1, A.sup.9=H, A.sup.10=Cl, A.sup.11=H, A.sup.12=Cl, A.sup.13=H], [2036; Q=Q.sup.r1, A.sup.9=CF.sub.3, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2037; Q=Q.sup.r1, A.sup.9=H, A.sup.10=CF.sub.3, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2038; Q=Q.sup.r1, A.sup.9=H, A.sup.10=H, A.sup.11=CF.sub.3, A.sup.12=H, A.sup.13=H], [2039; Q=Q.sup.r1, A.sup.9=CF.sub.3, A.sup.10=CF.sub.3, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2040; Q=Q.sup.r1, A.sup.9=CF.sub.3, A.sup.10=H, A.sup.11=CF.sub.3, A.sup.12=H, A.sup.13=H], [2041; Q=Q.sup.q11, A.sup.9=CF.sub.3, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=CF.sub.3], [2042; Q=Q.sup.r1, A.sup.9=H, A.sup.10=CF.sub.3, A.sup.11=CF.sub.3, A.sup.12=H, A.sup.13=H], [2043; Q=Q.sup.r1, A.sup.9=H, A.sup.10=CF.sub.3, A.sup.11=H, A.sup.12=CF.sub.3, A.sup.13=H], [2044; Q=Q.sup.r1, A.sup.9=OMe, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2045; Q=Q.sup.r1, A.sup.9=H, A.sup.10=OMe, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2046; Q=Q.sup.r1, A.sup.9=H, A.sup.10=H, A.sup.11=OMe, A.sup.12=H, A.sup.13=H], [2047; Q=Q.sup.r1, A.sup.9=OMe, A.sup.10=OMe, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2048; Q=Q.sup.r1, A.sup.9=OMe, A.sup.10=H, A.sup.11=OMe, A.sup.12=H, A.sup.13=H], [2049; Q=Q.sup.r1, A.sup.9=OMe, A.sup.10=H, A.sup.11=H, A.sup.1=H, A.sup.13=OMe], [2050; Q=Q.sup.r1, A.sup.9=H, A.sup.10=Me, A.sup.11=OMe, A.sup.12=H, A.sup.13=H], [2051; Q=Q.sup.r1, A.sup.9=H, A.sup.10=OMe, A.sup.11=H, A.sup.12=OMe, A.sup.13=H], [2052; Q=Q.sup.q11, A.sup.9=H, A.sup.10=Br, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2053; Q=Q.sup.r1, A.sup.9=H, A.sup.10=H, A.sup.11=Br, A.sup.12=H, A.sup.13=H], [2054; Q=Q.sup.r1, A.sup.9=Br, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=Br], [2055; Q=Q.sup.r1, A.sup.9=H, A.sup.10=Me, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2056; Q=Q.sup.r1, A.sup.9=H, A.sup.10=H, A.sup.11=Me, A.sup.12=H, A.sup.13=H], [2057; Q=Q.sup.r1, A.sup.9=Me, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=Me], [2058; Q=Q.sup.r1, A.sup.9=H, A.sup.10=cyclopropyl, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2059; Q=Q.sup.r1, A.sup.9=H, A.sup.10=H, A.sup.11=cyclopropyl, A.sup.12=H, A.sup.13=H], [2060; Q=Q.sup.r1, A.sup.7=cyclopropyl, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=cyclopropyl], [2061; Q=Q.sup.r1, A.sup.9=H, A.sup.10=OCHF.sub.2, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2062; Q=Q.sup.r1, A.sup.9=H, A.sup.10=H, A.sup.11=OCHF.sub.2, A.sup.12=H, A.sup.13=H], [2063; Q=Q.sup.r1, A.sup.9=H, A.sup.10=OCF.sub.3, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2064; Q=Q.sup.r1, A.sup.9=H, A.sup.10=H, A.sup.11=OCF.sub.3, A.sup.12=H, A.sup.13=H], [2065; Q=Q.sup.r2, A.sup.9=H, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2066; Q=Q.sup.r2, A.sup.9=F, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2067; Q=Q.sup.r2, A.sup.9=H, A.sup.10=F, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2068; Q=Q.sup.r2, A.sup.9=H, A.sup.10=H, A.sup.11=F, A.sup.12=H, A.sup.13=H], [2069; Q=Q.sup.r2, A.sup.9=F, A.sup.10=F, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2070; Q=Q.sup.r2, A.sup.9=F, A.sup.10=H, A.sup.11=F, A.sup.12=H, A.sup.13=H], [2071; Q=Q.sup.r2, A.sup.9=F, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=F], [2072; Q=Q.sup.r2, A.sup.9=H, A.sup.10=F, A.sup.1=F, A.sup.12=H, A.sup.13=H], [2073; Q=Q.sup.r2, A.sup.9=H, A.sup.1=F, A.sup.11=H, A.sup.12=F, A.sup.13=H], [2074; Q=Q.sup.r2, A.sup.9=Cl, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2075; Q=Q.sup.r2, A.sup.9=H, A.sup.10=Cl, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2076; Q=Q.sup.r2, A.sup.9=H, A.sup.10=H, A.sup.11=Cl, A.sup.12=H, A.sup.13=H], [2077; Q=Q.sup.r2, A.sup.9=Cl, A.sup.10=Cl, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2078; Q=Q.sup.r2, A.sup.9=Cl, A.sup.10=H, A.sup.11=Cl, A.sup.12=H, A.sup.13=H], [2079; Q=Q.sup.r2, A.sup.9=Cl, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=Cl], [2080; Q=Q.sup.r2, A.sup.9=H, A.sup.10=Cl, A.sup.11=Cl, A.sup.12=H, A.sup.13=H], [2081; Q=Q.sup.r2, A.sup.9=H, A.sup.10=Cl, A.sup.11=H, A.sup.12=Cl, A.sup.13=H], [2082; Q=Q.sup.r2, A.sup.9=CF.sub.3, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2083; Q=Q.sup.r2, A.sup.9=H, A.sup.10=CF.sub.3, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2084; Q=Q.sup.r2, A.sup.9=H, A.sup.10=H, A.sup.11=CF.sub.3, A.sup.12=H, A.sup.13=H], [2085; Q=Q.sup.r2, A.sup.9=CF.sub.3, A.sup.10=CF.sub.3, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2086; Q=Q.sup.r2, A.sup.9=CF.sub.3, A.sup.10=H, A.sup.11=CF.sub.3, A.sup.12=H, A.sup.13=H], [2087; Q=Q.sup.r2, A.sup.9=CF.sub.3, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=CF.sub.3], [2088; Q=Q.sup.r2, A.sup.9=H, A.sup.10=CF.sub.3, A.sup.1=CF.sub.3, A.sup.12=H, A.sup.13=H], [2089; Q=Q.sup.r2, A.sup.9=H, A.sup.10=CF.sub.3, A.sup.11=H, A.sup.12=CF.sub.3, A.sup.13=H], [2090; Q=Q.sup.r2, A.sup.9=OMe, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2091; Q=Q.sup.r2, A.sup.9=H, A.sup.10=OMe, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2092; Q=Q.sup.r2, A.sup.9=H, A.sup.10=H, A.sup.11=OMe, A.sup.12=H, A.sup.13=H], [2093; Q=Q.sup.r2, A.sup.9=OMe, A.sup.10=OMe, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2094; Q=Q.sup.r2, A.sup.9=OMe, A.sup.10=H, A.sup.11=OMe, A.sup.12=H, A.sup.13=H], [2095; Q=Q.sup.r2, A.sup.9=OMe, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=OMe], [2096; Q=Q.sup.r2, A.sup.9=H, A.sup.10=OMe, A.sup.11=OMe, A.sup.12=H, A.sup.13=H], [2097; Q=Q.sup.r2, A.sup.9=H, A.sup.10=OMe, A.sup.1=H, A.sup.12=OMe, A.sup.13=H], [2098; Q=Q.sup.r2, A.sup.9=H, A.sup.10=Br, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2099; Q=Q.sup.r2, A.sup.9=H, A.sup.10=H, A.sup.11=Br, A.sup.12=H, A.sup.13=H], [2100; Q=Q.sup.r2, A.sup.1=Br, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=Br], [2101; Q=Q.sup.r2, A.sup.9=H, A.sup.10=Me, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2102; Q=Q.sup.r2, A.sup.9=H, A.sup.10=H, A.sup.11=Me, A.sup.12=H, A.sup.13=H], [2103; Q=Q.sup.r2, A.sup.9=Me, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=Me], [2104; Q=Q.sup.r2, A.sup.9=H, A.sup.10=cyclopropyl, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2105; Q=Q.sup.r2, A.sup.9=H, A.sup.10=H, A.sup.11=cyclopropyl, A.sup.12=H, A.sup.13=H], [2106; Q=Q.sup.r2, A.sup.9=cyclopropyl, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=cyclopropyl], [2107; Q=Q.sup.r2, A.sup.1=H, A.sup.10=OCHF.sub.2, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2108; Q=Q.sup.r2, A.sup.9=H, A.sup.10=H, A.sup.11=OCHF.sub.2, A.sup.12=H, A.sup.13=H], [2109; Q=Q.sup.r2, A.sup.9=H, A.sup.10=OCF.sub.3, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2110; Q=Q.sup.r2, A.sup.9=H, A.sup.10=H, A.sup.11=OCF.sub.3, A.sup.12=H, A.sup.13=H], [2111; Q=Q.sup.r3, A.sup.9=H, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.3=H], [2112; Q=Q.sup.r3, A.sup.9=F, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2113; Q=Q.sup.q11, A.sup.9=H, A.sup.10=F, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2114; Q=Q.sup.r3, A.sup.9=H, A.sup.10=H, A.sup.11=F, A.sup.12=H, A.sup.13=H], [2115; Q=Q.sup.r3, A.sup.9=F, A.sup.10=F, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2116; Q=Q.sup.r3, A.sup.9=F, A.sup.10=H, A.sup.11=F, A.sup.12=H, A.sup.13=H], [2117; Q=Q.sup.r3, A.sup.9=F, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=F], [2118; Q=Q.sup.r3, A.sup.9=H, A.sup.10=F, A.sup.11=F, A.sup.12=H, A.sup.13=H], [2119; Q=Q.sup.r3, A.sup.9=H, A.sup.10=F, A.sup.1=H, A.sup.12=F, A.sup.13=H], [2120; Q=Q.sup.r3, A.sup.9=Cl, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2121; Q=Q.sup.r3, A.sup.9=H, A.sup.10=Cl, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2122; Q=Q.sup.r3, A.sup.9=H, A.sup.10=H, A.sup.11=Cl, A.sup.12=H, A.sup.13=H], [2123; Q=Q.sup.q11, A.sup.9=Cl, A.sup.10=Cl, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2124; Q=Q.sup.r3, A.sup.9=Cl, A.sup.10=H, A.sup.11=Cl, A.sup.12=H, A.sup.13=H], [2125; Q=Q.sup.r3, A.sup.9=Cl, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=Cl], [2126; Q=Q.sup.r3, A.sup.9=H, A.sup.10=Cl, A.sup.11=Cl, A.sup.12=H, A.sup.13=H], [2127; Q=Q.sup.r3, A.sup.9=H, A.sup.10=Cl, A.sup.11=H, A.sup.12=Cl, A.sup.13=H], [2128; Q=Q.sup.r3, A.sup.9=CF.sub.3, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2129; Q=Q.sup.r3, A.sup.9=H, A.sup.10=CF.sub.3, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2130; Q=Q.sup.r3, A.sup.9=H, A.sup.10=H, A.sup.11=CF.sub.3, A.sup.12=H, A.sup.13=H], [2131; Q=Q.sup.r3, A.sup.9=CF.sub.3, A.sup.10=CF.sub.3, A.sup.1=H, A.sup.12=H, A.sup.13=H], [2132; Q=Q.sup.r3, A.sup.9=CF.sub.3, A.sup.10=H, A.sup.11=CF.sub.3, A.sup.12=H, A.sup.13=H], [2133; Q=Q.sup.r3, A.sup.9=CF.sub.3, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=CF.sub.3], [2134; Q=Q.sup.r3, A.sup.9=H, A.sup.10=CF.sub.3, A.sup.11=CF.sub.3, A.sup.12=H, A.sup.13=H], [2135; Q=Q.sup.r3, A.sup.9=H, A.sup.10=CF.sub.3, A.sup.11=H, A.sup.12=CF.sub.3, A.sup.13=H], [2136; Q=Q.sup.r3, A.sup.9=OMe, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2137; Q=Q.sup.r3, A.sup.9=H, A.sup.10=OMe, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2138; Q=Q.sup.r3, A.sup.9=H, A.sup.10=H, A.sup.11=OMe, A.sup.12=H, A.sup.13=H], [2139; Q=Q.sup.r3, A.sup.9=OMe, A.sup.10=OMe, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2140; Q=Q.sup.r3, A.sup.9=OMe, A.sup.10=H, A.sup.11=OMe, A.sup.12=H, A.sup.13=H], [2141; Q=Q.sup.r3, A.sup.9=OMe, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=OMe], [2142; Q=Q.sup.r3, A.sup.9=H, A.sup.10=OMe, A.sup.1=OMe, A.sup.12=H, A.sup.13=H], [2143; Q=Q.sup.r3, A.sup.9=H, A.sup.10=OMe, A.sup.11=H, A.sup.12=OMe, A.sup.13=H], [2144; Q=Q.sup.r3, A.sup.9=H, A.sup.10=Br, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2145; Q=Q.sup.r3, A.sup.9=H, A.sup.10=H, A.sup.11=Br, A.sup.12=H, A.sup.13=H], [2146; Q=Q.sup.r3, A.sup.9=Br, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=Br], [2147; Q=Q.sup.r3, A.sup.9=H, A.sup.10=Me, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2148; Q=Q.sup.r3, A.sup.9=H, A.sup.10=H, A.sup.11=Me, A.sup.12=H, A.sup.13=H], [2149; Q=Q.sup.r3, A.sup.9=Me, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=Me], [2150; Q=Q.sup.r3, A.sup.9=H, A.sup.11=cyclopropyl, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2151; Q=Q.sup.r3, A.sup.9=H, A.sup.10=H, A.sup.7=cyclopropyl, A.sup.12=H, A.sup.13=H], [2152; Q=Q.sup.r3, A.sup.7=cyclopropyl, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=cyclopropyl], [2153; Q=Q.sup.r3, A.sup.9=H, A.sup.10=OCHF.sub.2, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2154; Q=Q.sup.r3, A.sup.9=H, A.sup.10=H, A.sup.11=OCHF.sub.2, A.sup.12=H, A.sup.13=H], [2155; Q=Q.sup.r3, A.sup.9=H, A.sup.10=OCF.sub.3, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2156; Q=Q.sup.r3, A.sup.9=H, A.sup.10=H, A.sup.11=OCF.sub.3, A.sup.12=H, A.sup.13=H], [2157; Q=Q.sup.r4, A.sup.9=H, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2158; Q=Q.sup.r4, A.sup.9=F, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2159; Q=Q.sup.r4, A.sup.9=H, A.sup.10=F, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2160; Q=Q.sup.r4, A.sup.9=H, A.sup.10=H, A.sup.11=F, A.sup.12=H, A.sup.13=H], [2161; Q=Q.sup.r4, A.sup.9=F, A.sup.10=F, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2162; Q=Q.sup.r4, A.sup.9=F, A.sup.10=H, A.sup.11=F, A.sup.12=H, A.sup.13=H], [2163; Q=Q.sup.r4, A.sup.9=F, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=F], [2164; Q=Q.sup.r4, A.sup.9=H, A.sup.10=F, A.sup.11=F, A.sup.12=H, A.sup.13=H], [2165; Q=Q.sup.r4, A.sup.9=H, A.sup.10=F, A.sup.11=H, A.sup.12=F, A.sup.13=H], [2166; Q=Q.sup.r4, A.sup.9=Cl, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2167; Q=Q.sup.r4, A.sup.9=H, A.sup.10=Cl, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2168; Q=Q.sup.r4, A.sup.9=H, A.sup.10=H, A.sup.11=Cl, A.sup.12=H, A.sup.13=H], [2169; Q=Q.sup.r4, A.sup.9=Cl, A.sup.10=Cl, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2170; Q=Q.sup.r4, A.sup.9=Cl, A.sup.10=H, A.sup.11=Cl, A.sup.12=H, A.sup.13=H], [2171; Q=Q.sup.r4, A.sup.9=Cl, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=Cl], [2172; Q=Q.sup.r4, A.sup.9=H, A.sup.10=Cl, A.sup.11=Cl, A.sup.12=H, A.sup.13=H], [2173; Q=Q.sup.r4, A.sup.9=H, A.sup.1=Cl, A.sup.1=H, A.sup.2=Cl, A.sup.13=H], [2174; Q=Q.sup.r4, A.sup.9=CF.sub.3, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2175; Q=Q.sup.r4, A.sup.9=H, A.sup.10=CF.sub.3, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2176; Q=Q.sup.r4, A.sup.9=H, A.sup.10=H, A.sup.11=CF.sub.3, A.sup.12=H, A.sup.13=H], [2177; Q=Q.sup.q11, A.sup.9=CF.sub.3, A.sup.10=CF.sub.3, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2178; Q=Q.sup.r4, A.sup.9=CF.sub.3, A.sup.10=H, A.sup.11=CF.sub.3, A.sup.12=H, A.sup.13=H], [2179; Q=Q.sup.r4, A.sup.9=CF.sub.3, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=CF.sub.3], [2180; Q=Q.sup.r4, A.sup.9=H, A.sup.10=CF.sub.3, A.sup.11=CF.sub.3, A.sup.12=H, A.sup.13=H], [2181; Q=Q.sup.r4, A.sup.9=H, A.sup.10=CF.sub.3, A.sup.11=H, A.sup.12=CF.sub.3, A.sup.13=H], [2182; Q=Q.sup.r4, A.sup.9=OMe, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2183; Q=Q.sup.r4, A.sup.9=H, A.sup.10=OMe, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2184; Q=Q.sup.r4, A.sup.9=H, A.sup.10=H, A.sup.11=OMe, A.sup.12=H, A.sup.13=H], [2185; Q=Q.sup.r4, A.sup.9=OMe, A.sup.10=OMe, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2186; Q=Q.sup.r4, A.sup.9=OMe, A.sup.10=H, A.sup.11=OMe, A.sup.12=H, A.sup.13=H], [2187; Q=Q.sup.r1, A.sup.9=OMe, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=OMe], [2188; Q=Q.sup.r4, A.sup.9=H, A.sup.10=OMe, A.sup.1=OMe, A.sup.12=H, A.sup.13=H], [2189; Q=Q.sup.r4, A.sup.9=H, A.sup.10=OMe, A.sup.11=H, A.sup.12=OMe, A.sup.13=H], [2190; Q=Q.sup.r4, A.sup.9=H, A.sup.10=Br, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2191; Q=Q.sup.r4, A.sup.9=H, A.sup.10=H, A.sup.11=Br, A.sup.12=H, A.sup.13=H], [2192; Q=Q.sup.r4, A.sup.9=Br, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=Br], [2193; Q=Q.sup.r4, A.sup.9=H, A.sup.10=Me, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2194; Q=Q.sup.r4, A.sup.9=H, A.sup.10=H, A.sup.11=Me, A.sup.12=H, A.sup.13=H], [2195; Q=Q.sup.r4, A.sup.9=Me, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=Me], [2196; Q=Q.sup.r1, A.sup.9=H, A.sup.11=cyclopropyl, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2197; Q=Q.sup.r4, A.sup.9=H, A.sup.10=H, A.sup.7=cyclopropyl, A.sup.12=H, A.sup.13=H], [2198; Q=Q.sup.r4, A.sup.9=cyclopropyl, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=cyclopropyl], [2199; Q=Q.sup.r4, A.sup.9=H, A.sup.10=OCHF.sub.2, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2200; Q=Q.sup.r4, A.sup.9=H, A.sup.10=H, A.sup.11=OCHF.sub.2, A.sup.12=H, A.sup.13=H], [2201; Q=Q.sup.r4, A.sup.9=H, A.sup.10=OCF.sub.3, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2202; Q=Q.sup.r4, A.sup.9=H, A.sup.10=H, A.sup.11=OCF.sub.3, A.sup.12=H, A.sup.13=H], [2203; Q=Q.sup.r5, A.sup.9=H, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2204; Q=Q.sup.r5, A.sup.9=F, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2205; Q=Q.sup.r5, A.sup.9=H, A.sup.10=F, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2206; Q=Q.sup.r5, A.sup.9=H, A.sup.10=H, A.sup.11=F, A.sup.12=H, A.sup.13=H], [2207; Q=Q.sup.r5, A.sup.9=F, A.sup.10=F, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2208; Q=Q.sup.q5, A.sup.9=F, A.sup.10=H, A.sup.11=F, A.sup.12=H, A.sup.13=H], [2209; Q=Q.sup.r5, A.sup.9=F, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=F], [2210; Q=Q.sup.r5, A.sup.9=H, A.sup.10=F, A.sup.11=F, A.sup.12=H, A.sup.13=H], [2211; Q=Q.sup.r5, A.sup.9=H, A.sup.10=F, A.sup.11=H, A.sup.12=F, A.sup.13=H], [2212; Q=Q.sup.r5, A.sup.9=Cl, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2213; Q=Q.sup.r5, A.sup.9=H, A.sup.10=Cl, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2214; Q=Q.sup.r5, A.sup.9=H, A.sup.10=H, A.sup.11=Cl, A.sup.12=H, A.sup.13=H], [2215; Q=Q.sup.r5, A.sup.9=Cl, A.sup.10=Cl, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2216; Q=Q.sup.r5, A.sup.9=Cl, A.sup.10=H, A.sup.11=Cl, A.sup.12=H, A.sup.13=H], [2217; Q=Q.sup.r5, A.sup.9=Cl, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=Cl], [2218; Q=Q.sup.r5, A.sup.9=H, A.sup.10=Cl, A.sup.11=Cl, A.sup.12=H, A.sup.13=H], [2219; Q=Q.sup.r5, A.sup.9=H, A.sup.10=Cl, A.sup.11=H, A.sup.12=Cl, A.sup.13=H], [2220; Q=Q.sup.r5, A.sup.9=CF.sub.3, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2221; Q=Q.sup.r5, A.sup.9=H, A.sup.10=CF.sub.3, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2222; Q=Q.sup.r5, A.sup.9=H, A.sup.10=H, A.sup.11=CF.sub.3, A.sup.12=H, A.sup.13=H], [2223; Q=Q.sup.r5, A.sup.9=CF.sub.3, A.sup.10=CF.sub.3, A.sup.1=H, A.sup.12=H, A.sup.13=H], [2224; Q=Q.sup.r5, A.sup.9=CF.sub.3, A.sup.10=H, A.sup.11=CF.sub.3, A.sup.12=H, A.sup.13=H], [2225; Q=Q.sup.r5, A.sup.9=CF.sub.3, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=CF.sub.3], [2226; Q=Q.sup.r5, A.sup.9=H, A.sup.10=CF.sub.3, A.sup.1=CF.sub.3, A.sup.12=H, A.sup.13=H], [2227; Q=Q.sup.r5, A.sup.9=H, A.sup.10=CF.sub.3, A.sup.11=H, A.sup.12=CF.sub.3, A.sup.13=H], [2228; Q=Q 5, A.sup.9=OMe, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2229; Q=Q.sup.q5, A.sup.9=H, A.sup.10=OMe, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2230; Q=Q.sup.r5, A.sup.9=H, A.sup.10=H, A.sup.11=OMe, A.sup.12=H, A.sup.13=H], [2231; Q=Q.sup.r5, A.sup.9=OMe, A.sup.10=OMe, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2232; Q=Q.sup.r5, A.sup.9=OMe, A.sup.10=H, A.sup.11=OMe, A.sup.12=H, A.sup.13=H], [2233; Q=Q.sup.q5, A.sup.9=OMe, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=OMe], [2234; Q=Q.sup.r5, A.sup.9=H, A.sup.10=OMe, A.sup.1=OMe, A.sup.12=H, A.sup.13=H], [2235; Q=Q.sup.r5, A.sup.9=H, A.sup.10=OMe, A.sup.11=H, A.sup.12=OMe, A.sup.13=H], [2236; Q=Q.sup.r5, A.sup.9=H, A.sup.10=Br, A.sup.11=H, A.sup.12=H, A.sup.1=H], [2237; Q=Q.sup.r5, A.sup.9=H, A.sup.10=H, A.sup.11=Br, A.sup.12=H, A.sup.13=H], [2238; Q=Q.sup.r1, A.sup.9=Br, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=Br], [2239; Q=Q.sup.r5, A.sup.9=H, A.sup.10=Me, A.sup.1=H, A.sup.12=H, A.sup.13=H], [2240; Q=Q.sup.r5, A.sup.9=H, A.sup.10=H, A.sup.11=Me, A.sup.12=H, A.sup.13=H], [2241; Q=Q.sup.r5, A.sup.9=Me, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=Me], [2242; Q=Q.sup.r5, A.sup.9=H, A.sup.10=cyclopropyl, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2243; Q=Q.sup.q5, A.sup.9=H, A.sup.10=H, A.sup.7=cyclopropyl, A.sup.12=H, A.sup.13=H], [2244; Q=Q.sup.q5, A.sup.7=cyclopropyl, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=cyclopropyl], [2245; Q=Q.sup.r5, A.sup.9=H, A.sup.10=OCHF.sub.2, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2246; Q=Q.sup.r5, A.sup.9=H, A.sup.10=H, A.sup.11=OCHF.sub.2, A.sup.12=H, A.sup.13=H], [2247; Q=Q.sup.r5, A.sup.9=H, A.sup.10=OCF.sub.3, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2248; Q=Q.sup.r1, A.sup.9=H, A.sup.10=H, A.sup.11=OCF.sub.3, A.sup.12=H, A.sup.13=H], [2249; Q=Q.sup.r6, A.sup.9=H, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2250; Q=Q.sup.r6, A.sup.9=F, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2251; Q=Q.sup.r6, A.sup.9=H, A.sup.10=F, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2252; Q=Q.sup.r6, A.sup.9=H, A.sup.10=H, A.sup.11=F, A.sup.12=H, A.sup.13=H], [2253; Q=Q.sup.r6, A.sup.9=F, A.sup.10=F, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2254; Q=Q.sup.r6, A.sup.9=F, A.sup.10=H, A.sup.11=F, A.sup.12=H, A.sup.13=H], [2255; Q=Q.sup.r6, A.sup.9=F, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=F], [2256; Q=Q.sup.r6, A.sup.9=H, A.sup.10=F, A.sup.11=F, A.sup.12=H, A.sup.13=H], [2257; Q=Q.sup.r6, A.sup.9=H, A.sup.10=F, A.sup.1=H, A.sup.2=F, A.sup.13=H], [2258; Q=Q.sup.r6, A.sup.9=Cl, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2259; Q=Q.sup.r6, A.sup.9=H, A.sup.10=Cl, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2260; Q=Q.sup.r6, A.sup.9=H, A.sup.10=H, A.sup.11=Cl, A.sup.12=H, A.sup.13=H], [2261; Q=Q.sup.r6, A.sup.9=Cl, A.sup.10=Cl, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2262; Q=Q.sup.r6, A.sup.9=Cl, A.sup.10=H, A.sup.11=Cl, A.sup.12=H, A.sup.13=H], [2263; Q=Q.sup.r6, A.sup.9=Cl, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=Cl], [2264; Q=Q.sup.r6, A.sup.9=H, A.sup.10=Cl, A.sup.11=Cl, A.sup.12=H, A.sup.13=H], [2265; Q=Q.sup.r6, A.sup.9=H, A.sup.10=Cl, A.sup.11=H, A.sup.12=Cl, A.sup.13=H], [2266; Q=Q.sup.r6, A.sup.9=CF.sub.3, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2267; Q=Q.sup.r6, A.sup.9=H, A.sup.10=CF.sub.3, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2268; Q=Q.sup.r6, A.sup.9=H, A.sup.10=H, A.sup.11=CF.sub.3, A.sup.12=H, A.sup.13=H], [2269; Q=Q.sup.r6, A.sup.9=CF.sub.3, A.sup.10=CF.sub.3, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2270; Q=Q.sup.r6, A.sup.9=CF.sub.3, A.sup.10=H, A.sup.1=CF.sub.3, A.sup.12=H, A.sup.13=H], [2271; Q=Q.sup.r6, A.sup.9=CF.sub.3, A.sup.10=H, A.sup.1=H, A.sup.12=H, A.sup.13=CF.sub.3], [2272; Q=Q.sup.r6, A.sup.9=H, A.sup.10=CF.sub.3, A.sup.11=CF.sub.3, A.sup.2=H, A.sup.13=H], [2273; Q=Q.sup.r6, A.sup.9=H, A.sup.10=CF.sub.3, A.sup.11=H, A.sup.12=CF.sub.3, A.sup.13=H], [2274; Q=Q.sup.r6, A.sup.9=OMe, A.sup.10=H, A.sup.5=H, A.sup.12=H, A.sup.13=H], [2275; Q=Q.sup.r6, A.sup.9=H, A.sup.10=OMe, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2276; Q=Q.sup.r1, A.sup.9=H, A.sup.10=H, A.sup.11=OMe, A.sup.12=H, A.sup.13=H], [2277; Q=Q.sup.r1, A.sup.9=OMe, A.sup.10=OMe, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2278; Q=Q.sup.r6, A.sup.9=OMe, A.sup.10=H, A.sup.11=OMe, A.sup.12=H, A.sup.13=H], [2279; Q=Q.sup.r6, A.sup.9=OMe, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=OMe], [2280; Q=Q.sup.r6, A.sup.9=H, A.sup.10=OMe, A.sup.1=OMe, A.sup.12=H, A.sup.13=H], [2281; Q=Q.sup.r6, A.sup.9=H, A.sup.10=OMe, A.sup.1=H, A.sup.12=OMe, A.sup.13=H], [2282; Q=Q.sup.r1, A.sup.9=H, A.sup.10=Br, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2283; Q=Q.sup.r6, A.sup.9=H, A.sup.10=H, A.sup.11=Br, A.sup.12=H, A.sup.13=H], [2284; Q=Q.sup.r6, A.sup.9=Br, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=Br], [2285; Q=Q.sup.r6, A.sup.9=H, A.sup.10=Me, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2286; Q=Q.sup.r6, A.sup.9=H, A.sup.10=H, A.sup.11=Me, A.sup.12=H, A.sup.13=H], [2287; Q=Q.sup.r6, A.sup.9=Me, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=Me], [2288; Q=Q.sup.r6, A.sup.9=H, A.sup.10=cyclopropyl, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2289; Q=Q.sup.r6, A.sup.9=H, A.sup.10=H, A.sup.7=cyclopropyl, A.sup.12=H, A.sup.13=H], [2290; Q=Q.sup.r6, A.sup.9=cyclopropyl, A.sup.10=H, A.sup.11=H, A.sup.12=H, A.sup.13=cyclopropyl], [2291; Q=Q.sup.r6, A.sup.9=H, A.sup.10=OCHF.sub.2, A.sup.11=H, A.sup.12=H, A.sup.1=H], [2292; Q=Q.sup.r6, A.sup.9=H, A.sup.10=H, A.sup.11=OCHF.sub.2, A.sup.2=H, A.sup.13=H], [2293; Q=Q.sup.r1, A.sup.9=H, A.sup.10=OCF.sub.3, A.sup.11=H, A.sup.12=H, A.sup.13=H], [2294; Q=Q.sup.r6, A.sup.9=H, A.sup.10=H, A.sup.11=OCF.sub.3, A.sup.12=H, A.sup.13=H], [2295; Q=Q.sup.r7, A.sup.14=H, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2296; Q=Q.sup.r7, A.sup.14=F, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2297; Q=Q.sup.r7, A.sup.14=H, A.sup.15=F, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2298; Q=Q.sup.r7, A.sup.14=H, A.sup.15=H, A.sup.16=F, A.sup.17=H, A.sup.18=H], [2299; Q=Q.sup.r7, A.sup.14=F, A.sup.15=F, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2300; Q=Q.sup.r7, A.sup.14=F, A.sup.15=H, A.sup.16=F, A.sup.17=H, A.sup.18=H], [2301; Q=Q.sup.r7, A.sup.14=F, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=F], [2302; Q=Q.sup.r7, A.sup.14=H, A.sup.15=F, A.sup.16=F, A.sup.1=H, A.sup.1=H], [2303; Q=Q.sup.r7, A.sup.14=H, A.sup.15=F, A.sup.16=H, A.sup.17=F, A.sup.18=H], [2304; Q=Q.sup.r7, A.sup.14=Cl, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2305; Q=Q.sup.r7, A.sup.14=H, A.sup.15=Cl, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2306; Q=Q.sup.r7, A.sup.14=H, A.sup.15=H, A.sup.16=Cl, A.sup.17=H, A.sup.18=H], [2307; Q=Q.sup.r7, A.sup.14=Cl, A.sup.15=Cl, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2308; Q=Q.sup.r7, A.sup.14=Cl, A.sup.15=H, A.sup.16=Cl, A.sup.17=H, A.sup.18=H], [2309; Q=Q.sup.r7, A.sup.14=Cl, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=Cl], [2310; Q=Q.sup.r7, A.sup.14=H, A.sup.15=Cl, A.sup.16=Cl, A.sup.17=H, A.sup.18=H], [2311; Q=Q.sup.r7, A.sup.14=H, A.sup.15=Cl, A.sup.1=H, A.sup.1=Cl, A.sup.18=H], [2312; Q=Q.sup.r7, A.sup.14=CF.sub.3, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2313; Q=Q.sup.r7, A.sup.14=H, A.sup.15=CF.sub.3, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2314; Q=Q.sup.r7, A.sup.14=H, A.sup.15=H, A.sup.16=CF.sub.3, A.sup.17=H, A.sup.18=H], [2315; Q=Q.sup.r7, A.sup.14=CF.sub.3, A.sup.15=CF.sub.3, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2316; Q=Q.sup.r7, A.sup.14=CF.sub.3, A.sup.15=H, A.sup.16=CF.sub.3, A.sup.17=H, A.sup.18=H], [2317; Q=Q.sup.r7, A.sup.14=CF.sub.3, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=CF.sub.3], [2318; Q=Q.sup.r7, A.sup.14=H, A.sup.15=CF.sub.3, A.sup.16=CF.sub.3, A.sup.17=H, A.sup.18=H], [2319; Q=Q.sup.r7, A.sup.14=H, A.sup.15=CF.sub.3, A.sup.16=H, A.sup.17=CF.sub.3, A.sup.18=H], [2320; Q=Q.sup.r7, A.sup.14=Me, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2321; Q=Q.sup.r7, A.sup.14=H, A.sup.15=OMe, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2322; Q=Q.sup.r7, A.sup.14=H, A.sup.15=H, A.sup.16=OMe, A.sup.17=H, A.sup.18=H], [2323; Q=Q.sup.r7, A.sup.14=OMe, A.sup.15=OMe, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2324; Q=Q.sup.r7, A.sup.14=OMe, A.sup.15=H, A.sup.16=OMe, A.sup.17=H, A.sup.18=H], [2325; Q=Q.sup.r7, A.sup.14=OMe, A.sup.5=H, A.sup.1=H, A.sup.17=H, A.sup.18=OMe], [2326; Q=Q.sup.r7, A.sup.14=H, A.sup.15=OMe, A.sup.16=OMe, A.sup.17=H, A.sup.18=H], [2327; Q=Q.sup.r7, A.sup.14=H, A.sup.15=OMe, A.sup.16=H, A.sup.17=OMe, A.sup.18=H], [2328; Q=Q.sup.r7, A.sup.14=H, A.sup.15=Br, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2329; Q=Q.sup.r7, A.sup.14=H, A.sup.15=H, A.sup.16=Br, A.sup.17=H, A.sup.18=H], [2330; Q=Q.sup.r7, A.sup.14=Br, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=Br], [2331; Q=Q.sup.r7, A.sup.14=H, A.sup.15=Me, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2332; Q=Q.sup.q7, A.sup.14=H, A.sup.15=H, A.sup.16=Me, A.sup.17=H, A.sup.18=H], [2333; Q=Q.sup.r7, A.sup.14=Me, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=Me], [2334; Q=Q.sup.r7, A.sup.14=H, A.sup.15=cyclopropyl, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2335; Q=Q.sup.r7, A.sup.14=H, A.sup.15=H, A.sup.16=cyclopropyl, A.sup.17=H, A.sup.18=H], [2336; Q=Q.sup.r7, A.sup.14=cyclopropyl, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=cyclopropyl], [2337; Q=Q.sup.r7, A.sup.14=H, A.sup.15=OCHF.sub.2, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2338; Q=Q.sup.r7, A.sup.14=H, A.sup.15=H, A.sup.16=OCHF.sub.2, A.sup.17=H, A.sup.18=H], [2339; Q=Q.sup.r7, A.sup.14=H, A.sup.15=OCF.sub.3, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2340; Q=Q.sup.r7, A.sup.14=H, A.sup.15=H, A.sup.16=OCF.sub.3, A.sup.17=H, A.sup.18=H], [2341; Q=Q.sup.r8, A.sup.14=H, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2342; Q=Q.sup.r8, A.sup.14=F, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2343; Q=Q.sup.r8, A.sup.14=H, A.sup.15=F, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2344; Q=Q.sup.r8, A.sup.14=H, A.sup.15=H, A.sup.16=F, A.sup.17=H, A.sup.18=H], [2345; Q=Q.sup.r8, A.sup.14=F, A.sup.15=F, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2346; Q=Q.sup.r8, A.sup.14=F, A.sup.15=H, A.sup.16=F, A.sup.17=H, A.sup.5=H], [2347; Q=Q.sup.r8, A.sup.14=F, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=F], [2348; Q=Q.sup.r8, A.sup.14=H, A.sup.15=F, A.sup.16=F, A.sup.17=H, A.sup.18=H], [2349; Q=Q.sup.r8, A.sup.14=H, A.sup.15=F, A.sup.16=H, A.sup.17=F, A.sup.18=H], [2350; Q=Q.sup.r8, A.sup.14=Cl, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2351; Q=Q.sup.r8, A.sup.14=H, A.sup.15=Cl, A.sup.16=H, A.sup.17=H, A.sup.5=H], [2352; Q=Q.sup.r8, A.sup.14=H, A.sup.15=H, A.sup.16=Cl, A.sup.17=H, A.sup.5=H], [2353; Q=Q.sup.r8, A.sup.14=Cl, A.sup.15=Cl, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2354; Q=Q.sup.r8, A.sup.14=Cl, A.sup.15=H, A.sup.16=Cl, A.sup.17=H, A.sup.18=H], [2355; Q=Q.sup.r8, A.sup.14=Cl, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=Cl], [2356; Q=Q.sup.r8, A.sup.14=H, A.sup.15=Cl, A.sup.16=Cl, A.sup.17=H, A.sup.18=H], [2357; Q=Q.sup.r8, A.sup.14=H, A.sup.15=Cl, A.sup.16=H, A.sup.17=Cl, A.sup.18=H], [2358; Q=Q.sup.r8, A.sup.14=CF.sub.3, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2359; Q=Q.sup.r5, A.sup.14=H, A.sup.15=CF.sub.3, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2360; Q=Q.sup.r8, A.sup.4=H, A.sup.5=H, A.sup.16=CF.sub.3, A.sup.17=H, A.sup.18=H], [2361; Q=Q.sup.r8, A.sup.14=CF.sub.3, A.sup.15=CF.sub.3, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2362; Q=Q.sup.r8, A.sup.14=CF.sub.3, A.sup.15=H, A.sup.16=CF.sub.3, A.sup.17=H, A.sup.18=H], [2363; Q=Q.sup.r8, A.sup.14=CF.sub.3, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=CF.sub.3], [2364; Q=Q.sup.r1, A.sup.14=H, A.sup.15=CF.sub.3, A.sup.16=CF.sub.3, A.sup.17=H, A.sup.18=H], [2365; Q=Q.sup.r8, A.sup.14=H, A.sup.15=CF.sub.3, A.sup.16=H, A.sup.17=CF.sub.3, A.sup.18=H], [2366; Q=Q.sup.r8, A.sup.14=OMe, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2367; Q=Q.sup.r8, A.sup.14=H, A.sup.15=OMe, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2368; Q=Q.sup.r8, A.sup.14=H, A.sup.15=H, A.sup.16=OMe, A.sup.17=H, A.sup.18=H], [2369; Q=Q.sup.r1, A.sup.14=OMe, A.sup.15=OMe, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2370; Q=Q.sup.r5, A.sup.14=OMe, A.sup.15=H, A.sup.6=OMe, A.sup.17=H, A.sup.18=H], [2371; Q=Q.sup.r8, A.sup.14=OMe, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=OMe], [2372; Q=Q.sup.r8, A.sup.14=H, A.sup.15=OMe, A.sup.16=OMe, A.sup.17=H, A.sup.18=H], [2373; Q=Q.sup.r8, A.sup.14=H, A.sup.15=OMe, A.sup.16=H, A.sup.17=OMe, A.sup.18=H], [2374; Q=Q.sup.r8, A.sup.14=H, A.sup.15=Br, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2375; Q=Q.sup.r8, A.sup.14=H, A.sup.15=H, A.sup.16=Br, A.sup.17=H, A.sup.18=H], [2376; Q=Q.sup.r8, A.sup.14=Br, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=Br], [2377; Q=Q.sup.r8, A.sup.1=H, A.sup.15=Me, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2378; Q=Q.sup.r8, A.sup.14=H, A.sup.15=H, A.sup.16=Me, A.sup.17=H, A.sup.18=H], [2379; Q=Q.sup.r8, A.sup.14=Me, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=Me], [2380; Q=Q.sup.r8, A.sup.14=H, A.sup.15=cyclopropyl, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2381; Q=Q.sup.r8, A.sup.14=H, A.sup.15=H, A.sup.16=cyclopropyl, A.sup.17=H, A.sup.18=H], [2382; Q=Q.sup.r8, A.sup.14=cyclopropyl, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=cyclopropyl], [2383; Q=Q.sup.r1, A.sup.14=H, A.sup.15=OCHF.sub.2, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2384; Q=Q.sup.r8, A.sup.14=H, A.sup.15=H, A.sup.16=OCHF.sub.2, A.sup.17=H, A.sup.18=H], [2385; Q=Q.sup.r8, A.sup.14=H, A.sup.15=OCF.sub.3, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2386; Q=Q.sup.r8, A.sup.14=H, A.sup.15=H, A.sup.16=OCF.sub.3, A.sup.17=H, A.sup.18=H], [2387; Q=Q.sup.r9, A.sup.14=H, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2388; Q=Q.sup.r9, A.sup.14=F, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2389; Q=Q.sup.r9, A.sup.14=H, A.sup.15=F, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2390; Q=Q.sup.r9, A.sup.14=H, A.sup.15=H, A.sup.16=F, A.sup.17=H, A.sup.18=H], [2391; Q=Q.sup.r9, A.sup.14=F, A.sup.15=F, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2392; Q=Q.sup.r9, A.sup.14=F, A.sup.15=H, A.sup.16=F, A.sup.17=H, A.sup.5=H], [2393; Q=Q.sup.r9, A.sup.14=F, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=F], [2394; Q=Q.sup.r9, A.sup.14=H, A.sup.15=F, A.sup.16=F, A.sup.17=H, A.sup.18=H], [2395; Q=Q.sup.r9, A.sup.14=H, A.sup.15=F, A.sup.16=H, A.sup.17=F, A.sup.18=H], [2396; Q=Q.sup.r9, A.sup.14=Cl, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2397; Q=Q.sup.r9, A.sup.14=H, A.sup.15=Cl, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2398; Q=Q.sup.r1, A.sup.14=H, A.sup.15=H, A.sup.16=Cl, A.sup.17=H, A.sup.18=H], [2399; Q=Q.sup.r9, A.sup.14=Cl, A.sup.15=Cl, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2400; Q=Q.sup.r9, A.sup.14=Cl, A.sup.15=H, A.sup.16=Cl, A.sup.17=H, A.sup.18=H], [2401; Q=Q.sup.r9, A.sup.14=Cl, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=Cl], [2402; Q=Q.sup.r9, A.sup.14=H, A.sup.15=Cl, A.sup.16=Cl, A.sup.17=H, A.sup.18=H], [2403; Q=Q.sup.r9, A.sup.14=H, A.sup.15=Cl, A.sup.16=H, A.sup.17=Cl, A.sup.18=H], [2404; Q=Q.sup.r9, A.sup.14=CF.sub.3, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2405; Q=Q.sup.r1, A.sup.14=H, A.sup.15=CF.sub.3, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2406; Q=Q.sup.r9, A.sup.4=H, A.sup.5=H, A.sup.16=CF.sub.3, A.sup.17=H, A.sup.18=H], [2407; Q=Q.sup.r9, A.sup.14=CF.sub.3, A.sup.15=CF.sub.3, A.sup.6=H, A.sup.17=H, A.sup.18=H], [2408; Q=Q.sup.r9, A.sup.14=CF.sub.3, A.sup.15=H, A.sup.16=CF.sub.3, A.sup.17=H, A.sup.18=H], [2409; Q=Q.sup.r9, A.sup.14=CF.sub.3, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=CF.sub.3], [2410; Q=Q.sup.r9, A.sup.14=H, A.sup.15=CF.sub.3, A.sup.16=CF.sub.3, A.sup.17=H, A.sup.18=H], [2411; Q=Q.sup.r9, A.sup.14=H, A.sup.15=CF.sub.3, A.sup.16=H, A.sup.17=CF.sub.3, A.sup.18=H], [2412; Q=Q.sup.r9, A.sup.14=OMe, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2413; Q=Q.sup.r9, A.sup.14=H, A.sup.15=OMe, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2414; Q=Q.sup.r9, A.sup.14=H, A.sup.15=H, A.sup.16=OMe, A.sup.17=H, A.sup.18=H], [2415; Q=Q.sup.r9, A.sup.14=OMe, A.sup.15=OMe, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2416; Q=Q.sup.r9, A.sup.14=OMe, A.sup.15=H, A.sup.6=OMe, A.sup.17=H, A.sup.18=H], [2417; Q=Q.sup.r9, A.sup.14=OMe, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=OMe], [2418; Q=Q.sup.r9, A.sup.14=H, A.sup.15=OMe, A.sup.16=OMe, A.sup.17=H, A.sup.18=H], [2419; Q=Q.sup.r9, A.sup.14=H, A.sup.15=OMe, A.sup.16=H, A.sup.17=OMe, A.sup.18=H], [2420; Q=Q.sup.r9, A.sup.14=H, A.sup.15=Br, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2421; Q=Q.sup.r9, A.sup.14=H, A.sup.15=H, A.sup.16=Br, A.sup.17=H, A.sup.18=H], [2422; Q=Q.sup.r9, A.sup.14=Br, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=Br], [2423; Q=Q.sup.r9, A.sup.14=H, A.sup.15=Me, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2424; Q=Q.sup.r9, A.sup.14=H, A.sup.15=H, A.sup.16=Me, A.sup.17=H, A.sup.18=H], [2425; Q=Q.sup.r9, A.sup.1=Me, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=Me], [2426; Q=Q.sup.r9, A.sup.14=H, A.sup.15=cyclopropyl, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2427; Q=Q.sup.r9, A.sup.14=H, A.sup.15=H, A.sup.16=cyclopropyl, A.sup.17=H, A.sup.18=H], [2428; Q=Q.sup.r9, A.sup.14=cyclopropyl, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=cyclopropyl], [2429; Q=Q.sup.r9, A.sup.14=H, A.sup.15=OCHF.sub.2, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2430; Q=Q.sup.r9, A.sup.14=H, A.sup.15=H, A.sup.16=OCHF.sub.2, A.sup.17=H, A.sup.18=H], [2431; Q=Q.sup.r9, A.sup.14=H, A.sup.15=OCF.sub.3, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2432; Q=Q.sup.r9, A.sup.14=H, A.sup.15=H, A.sup.16=OCF.sub.3, A.sup.17=H, A.sup.18=H], [2433; Q=Q.sup.r10, A.sup.14=H, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2434; Q=Q.sup.r10, A.sup.14=F, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2435; Q=Q.sup.r10, A.sup.14=H, A.sup.15=F, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2436; Q=Q.sup.r10, A.sup.14=H, A.sup.15=H, A.sup.16=F, A.sup.17=H, A.sup.18=H], [2437; Q=Q.sup.r10, A.sup.14=F, A.sup.15=F, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2438; Q=Q.sup.r10, A.sup.14=F, A.sup.15=H, A.sup.16=F, A.sup.17=H, A.sup.18=H], [2439; Q=Q.sup.r10, A.sup.14=F, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=F], [2440; Q=Q.sup.r10, A.sup.14=H, A.sup.15=F, A.sup.16=F, A.sup.17=H, A.sup.18=H], [2441; Q=Q.sup.r10, A.sup.14=H, A.sup.15=F, A.sup.16=H, A.sup.17=F, A.sup.18=H], [2442; Q=Q.sup.r10, A.sup.14=Cl, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2443; Q=Q.sup.r10, A.sup.14=H, A.sup.15=Cl, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2444; Q=Q.sup.r10, A.sup.14=H, A.sup.15=H, A.sup.16=Cl, A.sup.17=H, A.sup.18=H], [2445; Q=Q.sup.r10, A.sup.14=Cl, A.sup.15=Cl, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2446; Q=Q.sup.r10, A.sup.14=Cl, A.sup.15=H, A.sup.16=Cl, A.sup.17=H, A.sup.18=H], [2447; Q=Q.sup.r10, A.sup.14=Cl, A.sup.15=H, A.sup.6=H, A.sup.17=H, A.sup.18=Cl], [2448; Q=Q.sup.r10, A.sup.14=H, A.sup.15=Cl, A.sup.16=Cl, A.sup.17=H, A.sup.18=H], [2449; Q=Q.sup.r10, A.sup.14=H, A.sup.15=Cl, A.sup.16=H, A.sup.17=Cl, A.sup.18=H], [2450; Q=Q.sup.r10, A.sup.14=CF.sub.3, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2451; Q=Q.sup.r10, A.sup.14=H, A.sup.15=CF.sub.3, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2452; Q=Q.sup.r10, A.sup.14=H, A.sup.15=H, A.sup.16=CF.sub.3, A.sup.17=H, A.sup.18=H], [2453; Q=Q.sup.r10, A.sup.14=CF.sub.3, A.sup.15=CF.sub.3, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2454; Q=Q.sup.r10, A.sup.14=CF.sub.3, A.sup.15=H, A.sup.16=CF.sub.3, A.sup.17=H, A.sup.18=H], [2455; Q=Q.sup.r10, A.sup.14=CF.sub.3, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=CF.sub.3], [2456; Q=Q.sup.r10, A.sup.14=H, A.sup.15=CF.sub.3, A.sup.16=CF.sub.3, A.sup.17=H, A.sup.18=H], [2457; Q=Q.sup.r10, A.sup.14=H, A.sup.15=CF.sub.3, A.sup.16=H, A.sup.17=CF.sub.3, A.sup.18=H], [2458; Q=Q.sup.r10, A.sup.14=OMe, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2459; Q=Q.sup.r10, A.sup.14=H, A.sup.15=OMe, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2460; Q=Q.sup.r10, A.sup.14=H, A.sup.15=H, A.sup.16=OMe, A.sup.17=H, A.sup.18=H], [2461; Q=Q.sup.r10, A.sup.14=OMe, A.sup.15=OMe, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2462; Q=Q.sup.r10, A.sup.14=OMe, A.sup.15=H, A.sup.16=OMe, A.sup.17=H, A.sup.18=H], [2463; Q=Q.sup.r10, A.sup.14=OMe, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=OMe], [2464; Q=Q.sup.r10, A.sup.14=H, A.sup.15=OMe, A.sup.16=OMe, A.sup.17=H, A.sup.18=H], [2465; Q=Q.sup.r10, A.sup.14=H, A.sup.15=OMe, A.sup.16=H, A.sup.17=OMe, A.sup.1=H], [2466; Q=Q.sup.r10, A.sup.14=H, A.sup.15=Br, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2467; Q=Q.sup.r10, A.sup.14=H, A.sup.15=H, A.sup.16=Br, A.sup.17=H, A.sup.18=H], [2468; Q=Q.sup.r10, A.sup.14=Br, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=Br], [2469; Q=Q.sup.r10, A.sup.14=H, A.sup.15=Me, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2470; Q=Q.sup.r10, A.sup.14=H, A.sup.15=H, A.sup.16=Me, A.sup.17=H, A.sup.18=H], [2471; Q=Q.sup.r10, A.sup.14=Me, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=Me], [2472; Q=Q.sup.r10, A.sup.14=H, A.sup.15=cyclopropyl, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2473; Q=Q.sup.r10, A.sup.14=H, A.sup.15=H, A.sup.16=cyclopropyl, A.sup.17=H, A.sup.18=H], [2474; Q=Q.sup.r10, A.sup.14=cyclopropyl, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=cyclopropyl], [2475; Q=Q.sup.r10, A.sup.14=H, A.sup.15=OCHF.sub.2, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2476; Q=Q.sup.r10, A.sup.14=H, A.sup.15=H, A.sup.16=OCHF.sub.2, A.sup.17=H, A.sup.18=H], [2477; Q=Q.sup.r10, A.sup.14=H, A.sup.15=OCF.sub.3, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2478; Q=Q.sup.r10, A.sup.14=H, A.sup.15=H, A.sup.16=OCF.sub.3, A.sup.17=H, A.sup.18=H], [2479; Q=Q.sup.r10, A.sup.14=H, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2480; Q=Q.sup.r11, A.sup.14=F, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2481; Q=Q.sup.r11, A.sup.14=H, A.sup.15=F, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2482; Q=Q.sup.r11, A.sup.14=H, A.sup.15=H, A.sup.16=F, A.sup.17=H, A.sup.18=H], [2483; Q=Q.sup.r11, A.sup.14=F, A.sup.15=F, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2484; Q=Q.sup.r11, A.sup.14=F, A.sup.15=H, A.sup.16=F, A.sup.17=H, A.sup.5=H], [2485; Q=Q.sup.r11, A.sup.14=F, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=F], [2486; Q=Q.sup.r11, A.sup.14=H, A.sup.15=F, A.sup.16=F, A.sup.17=H, A.sup.18=H], [2487; Q=Q.sup.r11, A.sup.14=H, A.sup.15=F, A.sup.16=H, A.sup.17=F, A.sup.18=H], [2488; Q=Q.sup.r11, A.sup.14=Cl, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2489; Q=Q.sup.r11, A.sup.14=H, A.sup.15=Cl, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2490; Q=Q.sup.r11, A.sup.14=H, A.sup.15=H, A.sup.16=Cl, A.sup.17=H, A.sup.18=H], [2491; Q=Q.sup.r11, A.sup.14=Cl, A.sup.15=Cl, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2492; Q=Q.sup.r11, A.sup.14=Cl, A.sup.15=H, A.sup.16=Cl, A.sup.17=H, A.sup.18=H], [2493; Q=Q.sup.r11, A.sup.14=Cl, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=Cl], [2494; Q=Q.sup.r11, A.sup.14=H, A.sup.15=Cl, A.sup.16=Cl, A.sup.17=H, A.sup.18=H], [2495; Q=Q.sup.r11, A.sup.14=H, A.sup.15=Cl, A.sup.16=H, A.sup.17=Cl, A.sup.18=H], [2496; Q=Q.sup.r11, A.sup.14=CF.sub.3, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2497; Q=Q.sup.r11, A.sup.14=H, A.sup.15=CF.sub.3, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2498; Q=Q.sup.r11, A.sup.14=H, A.sup.15=H, A.sup.16=CF.sub.3, A.sup.17=H, A.sup.18=H], [2499; Q=Q.sup.r11, A.sup.14=CF.sub.3, A.sup.15=CF.sub.3, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2500; Q=Q.sup.r11, A.sup.14=CF.sub.3, A.sup.15=H, A.sup.16=CF.sub.3, A.sup.17=H, A.sup.18=H], [2501; Q=Q.sup.r11, A.sup.14=CF.sub.3, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=CF.sub.3], [2502; Q=Q.sup.r11, A.sup.14=H, A.sup.15=CF.sub.3, A.sup.16=CF.sub.3, A.sup.17=H, A.sup.18=H], [2503; Q=Q.sup.r11, A.sup.14=H, A.sup.15=CF.sub.3, A.sup.16=H, A.sup.17=CF.sub.3, A.sup.18=H], [2504; Q=Q.sup.r1, A.sup.14=OMe, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2505; Q=Q.sup.r11, A.sup.14=H, A.sup.15=OMe, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2506; Q=Q.sup.r11, A.sup.14=H, A.sup.15=H, A.sup.16=OMe, A.sup.17=H, A.sup.18=H], [2507; Q=Q.sup.r11, A.sup.14=Me, A.sup.15=OMe, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2508; Q=Q.sup.r11, A.sup.14=OMe, A.sup.15=H, A.sup.16=OMe, A.sup.17=H, A.sup.18=H], [2509; Q=Q.sup.r11, A.sup.14=OMe, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=OMe], [2510; Q=Q.sup.r11, A.sup.14=H, A.sup.15=OMe, A.sup.16=OMe, A.sup.17=H, A.sup.18=H], [2511; Q=Q.sup.r11, A.sup.14=H, A.sup.15=OMe, A.sup.16=H, A.sup.17=OMe, A.sup.18=H], [2512; Q=Q.sup.r11, A.sup.14=H, A.sup.15=Br, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2513; Q=Q.sup.r11, A.sup.14=H, A.sup.15=H, A.sup.16=Br, A.sup.17=H, A.sup.18=H], [2514; Q=Q.sup.r11, A.sup.14=Br, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=Br], [2515; Q=Q.sup.r11, A.sup.14=H, A.sup.15=Me, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2516; Q=Q.sup.r11, A.sup.14=H, A.sup.15=H, A.sup.16=Me, A.sup.17=H, A.sup.18=H], [2517; Q=Q.sup.r111, A.sup.14=Me, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=Me], [2518; Q=Q.sup.r11, A.sup.14=H, A.sup.15=cyclopropyl, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2519; Q=Q.sup.r11, A.sup.14=H, A.sup.15=H, A.sup.16=cyclopropyl, A.sup.17=H, A.sup.18=H], [2520; Q=Q.sup.r11, A.sup.17=cyclopropyl, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=cyclopropyl], [2521; Q=Q.sup.r11, A.sup.14=H, A.sup.15=OCHF.sub.2, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2522; Q=Q.sup.r1, A.sup.14=H, A.sup.15=H, A.sup.16=OCHF.sub.2, A.sup.17=H, A.sup.18=H], [2523; Q=Q.sup.r11, A.sup.14=H, A.sup.15=OCF.sub.3, A.sup.6=H, A.sup.17=H, A.sup.18=H], [2524; Q=Q.sup.r11, A.sup.14=H, A.sup.15=H, A.sup.16=OCF.sub.3, A.sup.17=H, A.sup.18=H], [2525; Q=Q.sup.r12, A.sup.14=H, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2526; Q=Q.sup.r12, A.sup.14=F, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2527; Q=Q.sup.r12, A.sup.14=H, A.sup.15=F, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2528; Q=Q.sup.r12, A.sup.14=H, A.sup.15=H, A.sup.16=F, A.sup.17=H, A.sup.18=H], [2529; Q=Q.sup.r12, A.sup.14=F, A.sup.15=F, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2530; Q=Q.sup.r12, A.sup.14=F, A.sup.15=H, A.sup.16=F, A.sup.17=H, A.sup.18=H], [2531; Q=Q.sup.r12, A.sup.14=F, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.1=F], [2532; Q=Q.sup.r12, A.sup.14=H, A.sup.15=F, A.sup.16=F, A.sup.17=H, A.sup.18=H], [2533; Q=Q.sup.r12, A.sup.14=H, A.sup.15=F, A.sup.16=H, A.sup.17=F, A.sup.18=H], [2534; Q=Q.sup.r12, A.sup.14=Cl, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2535; Q=Q.sup.r12, A.sup.14=H, A.sup.15=Cl, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2536; Q=Q.sup.r12, A.sup.14=H, A.sup.15=H, A.sup.16=Cl, A.sup.17=H, A.sup.18=H], [2537; Q=Q.sup.r12, A.sup.14=Cl, A.sup.15=Cl, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2538; Q=Q.sup.r12, A.sup.14=Cl, A.sup.15=H, A.sup.16=Cl, A.sup.17=H, A.sup.18=H], [2539; Q=Q.sup.r12, A.sup.14=Cl, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=Cl], [2540; Q=Q.sup.r12, A.sup.14=H, A.sup.15=Cl, A.sup.16=Cl, A.sup.17=H, A.sup.18=H], [2541; Q=Q.sup.r12, A.sup.14=H, A.sup.15=Cl, A.sup.16=H, A.sup.17=Cl, A.sup.18=H], [2542; Q=Q.sup.r12, A.sup.14=CF.sub.3, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2543; Q=Q.sup.r2, A.sup.14=H, A.sup.15=CF.sub.3, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2544; Q=Q.sup.r12, A.sup.14=H, A.sup.15=H, A.sup.16=CF.sub.3, A.sup.17=H, A.sup.18=H], [2545; Q=Q.sup.r12, A.sup.14=CF.sub.3, A.sup.15=CF.sub.3, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2546; Q=Q.sup.r12, A.sup.14=CF.sub.3, A.sup.15=H, A.sup.16=CF.sub.3, A.sup.17=H, A.sup.18=H], [2547; Q=Q.sup.r2, A.sup.14=CF.sub.3, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=CF.sub.3], [2548; Q=Q.sup.r12, A.sup.14=H, A.sup.15=CF.sub.3, A.sup.16=CF.sub.3, A.sup.17=H, A.sup.18=H], [2549; Q=Q.sup.r12, A.sup.14=H, A.sup.15=CF.sub.3, A.sup.16=H, A.sup.17=CF.sub.3, A.sup.18=H], [2550; Q=Q.sup.r12, A.sup.14=OMe, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2551; Q=Q.sup.r12, A.sup.18=H, A.sup.1=OMe, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2552; Q=Q.sup.r12, A.sup.14=H, A.sup.15=H, A.sup.16=OMe, A.sup.17=H, A.sup.18=H], [2553; Q=Q.sup.r2, A.sup.14=OMe, A.sup.15=OMe, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2554; Q=Q.sup.r12, A.sup.14=OMe, A.sup.15=H, A.sup.16=OMe, A.sup.17=H, A.sup.18=H], [2555; Q=Q.sup.r12, A.sup.14=OMe, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=OMe], [2556; Q=Q.sup.r12, A.sup.14=H, A.sup.15=OMe, A.sup.16=OMe, A.sup.17=H, A.sup.18=H], [2557; Q=Q.sup.r12, A.sup.18=H, A.sup.15=OMe, A.sup.16=H, A.sup.17=OMe, A.sup.18=H], [2558; Q=Q.sup.r12, A.sup.14=H, A.sup.15=Br, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2559; Q=Q.sup.r12, A.sup.14=H, A.sup.15=H, A.sup.16=Br, A.sup.17=H, A.sup.18=H], [2560; Q=Q.sup.r12, A.sup.14=Br, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=Br], [2561; Q=Q.sup.r12, A.sup.14=H, A.sup.15=Me, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2562; Q=Q.sup.r12, A.sup.14=H, A.sup.15=H, A.sup.16=Me, A.sup.17=H, A.sup.18=H], [2563; Q=Q.sup.r12, A.sup.14=Me, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=Me], [2564; Q=Q.sup.r12, A.sup.14=H, A.sup.15=cyclopropyl, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2565; Q=Q.sup.r12, A.sup.14=H, A.sup.15=H, A.sup.16=cyclopropyl, A.sup.17=H, A.sup.18=H], [2566; Q=Q.sup.r12, A.sup.14=cyclopropyl, A.sup.15=H, A.sup.16=H, A.sup.17=H, A.sup.18=cyclopropyl], [2567; Q=Q.sup.r12, A.sup.14=H, A.sup.15=OCHF.sub.2, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2568; Q=Q.sup.r12, A.sup.14=H, A.sup.15=H, A.sup.16=OCHF.sub.2, A.sup.17=H, A.sup.18=H], [2569; Q=Q.sup.r12, A.sup.14=H, A.sup.15=OCF.sub.3, A.sup.16=H, A.sup.17=H, A.sup.18=H], [2570; Q=Q.sup.r12, A.sup.14=H, A.sup.15=H, A.sup.16=OCF.sub.3, A.sup.17=H, A.sup.18=H], [2571; Q=Q.sup.r13, A.sup.20=H, A.sup.21=H, A.sup.22=H], [2572; Q=Q.sup.r13, A.sup.20=Me, A.sup.21=H, A.sup.22=H], [2573; Q=Q.sup.r13, A.sup.20=H, A.sup.21=Me, A.sup.22=H], [2574; Q=Q.sup.r13, A.sup.20=H, A.sup.21=H, A.sup.22=Me], [2575; Q=Q.sup.r13, A.sup.20=Me, A.sup.21=Me, A.sup.22=H], [2576; Q=Q.sup.r13, A.sup.20=Me, A.sup.21=H, A.sup.22=Me], [2577; Q=Q.sup.r13, A.sup.20=H, A.sup.21=Me, A.sup.22=Me], [2578; Q=Q.sup.r13, A.sup.20=Me, A.sup.21=Me, A.sup.22=Me], [2579; Q=Q.sup.r13, A.sup.20=H, A.sup.21=H, A.sup.22=Cl], [2580; Q=Q.sup.r13, A.sup.20=H, A.sup.21=H, A.sup.22=CF.sub.3], [2581; Q=Q.sup.r13, A.sup.20=H, A.sup.21=H, A.sup.22=OMe], [2582; Q=Q.sup.r14, A.sup.20=H, A.sup.21=H, A.sup.23=H], [2583; Q=Q.sup.r14, A.sup.20=Me, A.sup.21=H, A.sup.23=H], [2584; Q=Q.sup.r14, A.sup.20=H, A.sup.21=Me, A.sup.23=H], [2585; Q=Q.sup.r14, A.sup.20=H, A.sup.21=H, A.sup.23=Me], [2586; Q=Q.sup.r14, A.sup.20=Me, A.sup.21=Me, A.sup.23=H], [2587; Q=Q.sup.r14, A.sup.20=Me, A.sup.21=H, A.sup.23=Me], [2588; =Q.sup.r14, A.sup.20=H, A.sup.21=Me, A.sup.23=Me], [2589; Q=Q.sup.r4, A.sup.20=Me, A.sup.21=Me, A.sup.23=Me], [2590; Q=Q.sup.r14, A.sup.20=H, A.sup.21=Cl, A.sup.23=H], [2591; Q=Q.sup.q11, A.sup.20=H, A.sup.21=CF.sub.3, A.sup.23=H], [2592; Q=Q.sup.r14, A.sup.20=H, A.sup.21=OMe, A.sup.23=H], [2593; Q=Q.sup.r14, A.sup.20=H, A.sup.21=H, A.sup.23=Cl], [2594; Q=Q.sup.r14, A.sup.20=H, A.sup.21=H, A.sup.23=CF.sub.3], [2595; Q=Q.sup.r14, A.sup.20=H, A.sup.21=H, A.sup.23=OMe], [2596; Q=Q.sup.r15, A.sup.24=H, A.sup.25=H, A.sup.26=H], [2597; Q=Q.sup.r15, A.sup.24=Me, A.sup.25=H, A.sup.26=H], [2598; Q=Q.sup.r15, A.sup.24=H, A.sup.25=Me, A.sup.26=H], [2599; Q=Q.sup.r15, A.sup.24=H, A.sup.25=H, A.sup.26=Me], [2600; Q=Q.sup.r15, A.sup.24=Me, A.sup.25=Me, A.sup.26=H], [2601; Q=Q.sup.r15, A.sup.24=Me, A.sup.25=H, A.sup.26=Me], [2602; Q=Q.sup.r15, A.sup.24=H, A.sup.25=Me, A.sup.26=Me], [2603; Q=Q.sup.r5, A.sup.24=Me, A.sup.25=Me, A.sup.26=Me], [2604; Q=Q.sup.r15, A.sup.24=H, A.sup.25=H, A.sup.26=Cl], [2605; Q=Q.sup.r1, A.sup.24=H, A.sup.25=H, A.sup.26=CF.sub.3], [2606; Q=Q.sup.r15, A.sup.24=H, A.sup.25=H, A.sup.26=OMe], [2607; Q=Q.sup.r16, A.sup.24=H, A.sup.25=H, A.sup.27=H], [2608; Q=Q.sup.r16, A.sup.24=Me, A.sup.25=H, A.sup.27=H], [2609; Q=Q.sup.r16, A.sup.24=H, A.sup.25=Me, A.sup.27=H], [2610; Q=Q.sup.r16, A.sup.24=H, A.sup.25=H, A.sup.27=Me], [2611; Q=Q.sup.r1, A.sup.24=Me, A.sup.25=Me, A.sup.27=H], [2612; Q=Q.sup.r16, A.sup.24=Me, A.sup.25=H, A.sup.27=Me], [2613; Q=Q.sup.r16, A.sup.24=H, A.sup.25=Me, A.sup.27=Me], [2614; Q=Q.sup.r16, A.sup.24=Me, A.sup.25=Me, A.sup.27=Me], [2615; Q=Q.sup.r16, A.sup.24=H, A.sup.25=Cl, A.sup.27=H], [2616; Q=Q.sup.r16, A.sup.24=H, A.sup.25=CF.sub.3, A.sup.27=H], [2617; Q=Q.sup.r16, A.sup.24=H, A.sup.25=OMe, A.sup.27=H], [2618; Q=Q.sup.r1, A.sup.24=H, A.sup.25=H, A.sup.27=Cl], [2619; Q=Q.sup.r16, A.sup.24=H, A.sup.25=H, A.sup.27=CF.sub.3], [2620; Q=Q.sup.r16, A.sup.24=H, A.sup.25=H, A.sup.27=OMe], [2630; Q=Q.sup.s1, A.sup.28=H, A.sup.29=H, A.sup.30=H, A.sup.31=H, A.sup.32=H], [2631; Q=Q.sup.s19, A.sup.28=H, A.sup.29=F, A.sup.30=H, A.sup.31=H, A.sup.32=H], [2632; Q=Q.sup.s1, A.sup.28=H, A.sup.29=H, A.sup.30=F, A.sup.31=H, A.sup.32=H], [2633; Q=Q.sup.s1, A.sup.28=F, A.sup.29=H, A.sup.30=H, A.sup.31=H, A.sup.32=F], [2634; Q=Q.sup.s1, A.sup.28=H, A.sup.29=F, A.sup.30=H, A.sup.1=F, A.sup.32=H], [2635; Q=Q.sup.s1, A.sup.28=H, A.sup.29=Cl, A.sup.30=H, A.sup.31=H, A.sup.32=H], [2636; Q=Q.sup.s1, A.sup.28=H, A.sup.29=H, A.sup.30=Cl, A.sup.31=H, A.sup.32=H], [2637; Q=Q.sup.s1, A.sup.28=Cl, A.sup.29=Cl, A.sup.30=H, A.sup.31=H, A.sup.32=H], [2638; Q=Q.sup.s1, A.sup.28=Cl, A.sup.29=H, A.sup.30=H, A.sup.3=H, A.sup.32=Cl], [2639; Q=Q.sup.s1, A.sup.28=H, A.sup.29=Cl, A.sup.30=H, A.sup.31=Cl, A.sup.32=H], [2640; Q=Q.sup.s1, A.sup.28=H, A.sup.29=CF.sub.3, A.sup.30=H, A.sup.31=H, A.sup.32=H], [2641; Q=Q.sup.s1, A.sup.28=H, A.sup.29=H, A.sup.30=CF.sub.3, A.sup.31=H, A.sup.32=H], [2642; Q=Q.sup.s1, A.sup.28=H, A.sup.29=OMe, A.sup.30=H, A.sup.31=H, A.sup.32=H], [2643; Q=Q.sup.s1, A.sup.28=H, A.sup.29=H, A.sup.30=OMe, A.sup.31=H, A.sup.32=H], [2644; Q=Q.sup.s1, A.sup.28=OMe, A.sup.29=H, A.sup.30=H, A.sup.31=H, A.sup.32=OMe], [2645; Q=Q.sup.q11, A.sup.28=H, A.sup.29=OMe, A.sup.30=H, A.sup.31=OMe, A.sup.32=H], [2646; Q=Q.sup.s1, A.sup.28=H, A.sup.29=Br, A.sup.30=H, A.sup.31=H, A.sup.32=H], [2647; Q=Q.sup.s1, A.sup.28=H, A.sup.29=H, A.sup.30=Br, A.sup.31=H, A.sup.32=H], [2648; Q=Q.sup.s1, A.sup.28=Br, A.sup.29=H, A.sup.30=H, A.sup.31=H, A.sup.32=Br], [2649; Q=Q.sup.q5, A.sup.28=H, A.sup.29=Me, A.sup.30=H, A.sup.31=H, A.sup.32=H], [2650; Q=Q.sup.s1, A.sup.28=H, A.sup.29=H, A.sup.30=Me, A.sup.31=H, A.sup.32=H], [2651; Q=Q.sup.s1, A.sup.28=Me, A.sup.29=H, A.sup.30=H, A.sup.31=H, A.sup.32=Me], [2652; Q=Q.sup.s1, A.sup.28=H, A.sup.29=cyclopropyl, A.sup.30=H, A.sup.31=H, A.sup.32=H], [2653; Q=Q.sup.s1, A.sup.28=H, A.sup.29=H, A.sup.30=cyclopropyl, A.sup.31=H, A.sup.32=H], [2654; Q=Q.sup.s1, A.sup.28=cyclopropyl, A.sup.29=H, A.sup.30=H, A.sup.31=H, A.sup.32=cyclopropyl], [2655; Q=Q.sup.s1, A.sup.28=H, A.sup.29=OCHF.sub.2, A.sup.30=H, A.sup.31=H, A.sup.32=H], [2656; Q=Q.sup.s1, A.sup.28=H, A.sup.29=H, A.sup.30=OCHF.sub.2, A.sup.31=H, A.sup.32=H], [2657; Q=Q.sup.s1, A.sup.28=H, A.sup.29=OCF.sub.3, A.sup.30=H, A.sup.31=H, A.sup.32=H], [2658; Q=Q.sup.s1, A.sup.28=H, A.sup.29=H, A.sup.30=OCF.sub.3, A.sup.31=H, A.sup.32=H], [2659; Q=Q.sup.s2, A.sup.28=H, A.sup.29=H, A.sup.30=H, A.sup.31=H, A.sup.32=H], [2660; Q=Q.sup.s2, A.sup.28=H, A.sup.29=F, A.sup.30=H, A.sup.31=H, A.sup.32=H], [2661; Q=Q.sup.q2, A.sup.28=H, A.sup.29=H, A.sup.30=F, A.sup.31=H, A.sup.32=H], [2662; Q=Q.sup.s2, A.sup.28=F, A.sup.29=H, A.sup.30=H, A.sup.31=H, A.sup.32=F], [2663; Q=Q.sup.s2, A.sup.28=H, A.sup.29=F, A.sup.30=H, A.sup.1=F, A.sup.32=H], [2664; Q=Q.sup.s2, A.sup.28=H, A.sup.29=Cl, A.sup.30=H, A.sup.31=H, A.sup.32=H], [2665; Q=Q.sup.s2, A.sup.28=H, A.sup.29=H, A.sup.30=Cl, A.sup.31=H, A.sup.32=H], [2666; Q=Q.sup.s2, A.sup.28=Cl, A.sup.29=Cl, A.sup.30=H, A.sup.31=H, A.sup.32=H], [2667; Q=Q.sup.s2, A.sup.28=Cl, A.sup.29=H, A.sup.30=H, A.sup.31=H, A.sup.32=Cl], [2668; Q=Q.sup.s2, A.sup.28=H, A.sup.29=Cl, A.sup.30=H, A.sup.31=Cl, A.sup.32=H], [2669; Q=Q.sup.s2, A.sup.28=H, A.sup.29=CF.sub.3, A.sup.30=H, A.sup.31=H, A.sup.32=H], [2670; Q=Q.sup.s2, A.sup.28=H, A.sup.29=H, A.sup.30=CF.sub.3, A.sup.31=H, A.sup.32=H], [2671; Q=Q.sup.s2, A.sup.28=H, A.sup.29=OMe, A.sup.30=H, A.sup.31=H, A.sup.32=H], [2672; Q=Q.sup.s2, A.sup.28=H, A.sup.29=H, A.sup.30=OMe, A.sup.31=H, A.sup.32=H], [2673; Q=Q.sup.s2, A.sup.28=Me, A.sup.29=H, A.sup.30=H, A.sup.31=H, A.sup.32=OMe], [2674; Q=Q.sup.s2, A.sup.28=H, A.sup.29=OMe, A.sup.30=H, A.sup.31=OMe, A.sup.32=H], [2675; Q=Q.sup.q2, A.sup.28=H, A.sup.29=Br, A.sup.30=H, A.sup.31=H, A.sup.32=H], [2676; Q=Q.sup.q2, A.sup.28=H, A.sup.29=H, A.sup.30=Br, A.sup.31=H, A.sup.32=H], [2677; Q=Q.sup.q2, A.sup.28=Br, A.sup.29=H, A.sup.30=H, A.sup.31=H, A.sup.32=Br], [2678; Q=Q.sup.s2, A.sup.28=H, A.sup.29=Me, A.sup.30=H, A.sup.31=H, A.sup.32=H], [2679; Q=Q.sup.s2, A.sup.28=H, A.sup.29=H, A.sup.30=Me, A.sup.31=H, A.sup.32=H], [2680; Q=Q.sup.s2, A.sup.28=Me, A.sup.29=H, A.sup.30=H, A.sup.31=H, A.sup.32=Me], [2681; Q=Q.sup.s2, A.sup.28=H, A.sup.29=cyclopropyl, A.sup.30=H, A.sup.31=H, A.sup.32=H], [2682; Q=Q.sup.s2, A.sup.28=H, A.sup.29=H, A.sup.30=cyclopropyl, A.sup.31=H, A.sup.32=H], [2683; Q=Q.sup.s2, A.sup.28=cyclopropyl, A.sup.29=H, A.sup.30=H, A.sup.31=H, A.sup.32=cyclopropyl], [2684; Q=Q.sup.s2, A.sup.28=H, A.sup.29=OCHF.sub.2, A.sup.30=H, A.sup.31=H, A.sup.32=H], [2685; Q=Q.sup.s2, A.sup.28=H, A.sup.29=H, A.sup.30=OCHF.sub.2, A.sup.31=H, A.sup.32=H], [2686; Q=Q.sup.s2, A.sup.28=H, A.sup.29=OCF.sub.3, A.sup.30=H, A.sup.31=H, A.sup.32=H], [2687; Q=Q.sup.s2, A.sup.28=H, A.sup.29=H, A.sup.30=OCF.sub.3, A.sup.31=H, A.sup.32=H], [2688; Q=Q.sup.s1, A.sup.28=H, A.sup.29=H, A.sup.30=H, A.sup.31=H, A.sup.32=H], [2689; Q=Q.sup.s1, A.sup.28=H, A.sup.29=F, A.sup.30=H, A.sup.31=H, A.sup.32=H], [2690; Q=Q.sup.s1, A.sup.28=H, A.sup.29=H, A.sup.30=F, A.sup.31=H, A.sup.32=H], [2691; Q=Q.sup.s1, A.sup.28=F, A.sup.29=H, A.sup.30=H, A.sup.31=H, A.sup.32=F], [2692; Q=Q.sup.s1, A.sup.28=H, A.sup.29=F, A.sup.30=H, A.sup.31=F, A.sup.32=H], [2693; Q=Q.sup.s1, A.sup.28=H, A.sup.29=Cl, A.sup.30=H, A.sup.31=H, A.sup.32=H], [2694; Q=Q.sup.s3, A.sup.28=H, A.sup.29=H, A.sup.30=Cl, A.sup.31=H, A.sup.32=H], [2695; Q=Q.sup.s1, A.sup.28=Cl, A.sup.29=Cl, A.sup.30=H, A.sup.31=H, A.sup.32=H], [2696; Q=Q.sup.s3, A.sup.28=Cl, A.sup.29=H, A.sup.30=H, A.sup.31=H, A.sup.32=Cl], [2697; Q=Q.sup.s3, A.sup.28=H, A.sup.29=Cl, A.sup.30=H, A.sup.31=Cl, A.sup.32=H], [2698; Q=Q.sup.s3, A.sup.28=H, A.sup.29=CF.sub.3, A.sup.30=H, A.sup.31=H, A.sup.32=H], [2699; Q=Q.sup.s3, A.sup.28=H, A.sup.29=H, A.sup.30=CF.sub.3, A.sup.31=H, A.sup.32=H], [2700; Q=Q.sup.s3, A.sup.28=H, A.sup.29=OMe, A.sup.30=H, A.sup.31=H, A.sup.32=H], [2701; Q=Q.sup.s3, A.sup.28=H, A.sup.29=H, A.sup.30=, A.sup.31=H, A.sup.32=H], [2702; Q=Q.sup.s3, A.sup.28=OMe, A.sup.29=H, A.sup.30=H, A.sup.31=H, A.sup.32=OMe], [2703; Q=Q.sup.s1, A.sup.28=H, A.sup.29=OMe, A.sup.30=H, A.sup.31=OMe, A.sup.32=H], [2704; Q=Q.sup.s1, A.sup.28=H, A.sup.29=Br, A.sup.30=H, A.sup.31=H, A.sup.32=H], [2705; Q=Q.sup.s3, A.sup.28=H, A.sup.29=H, A.sup.30=Br, A.sup.31=H, A.sup.32=H], [2706; Q=Q.sup.s3, A.sup.28=Br, A.sup.29=H, A.sup.30=H, A.sup.31=H, A.sup.32=Br], [2707; Q=Q.sup.s3, A.sup.28=H, A.sup.29=Me, A.sup.30=H, A.sup.31=H, A.sup.32=H], [2708; Q=Q.sup.s3, A.sup.28=H, A.sup.29=H, A.sup.30=Me, A.sup.31=H, A.sup.32=H], [2709; Q=Q.sup.s3, A.sup.28=Me, A.sup.29=H, A.sup.30=H, A.sup.31=H, A.sup.32=Me], [2710; Q=Q.sup.s3, A.sup.28=H, A.sup.29=cyclopropyl, A.sup.30=H, A.sup.31=H, A.sup.32=H], [2711; Q=Q.sup.s3, A.sup.28=H, A.sup.29=H, A.sup.30=cyclopropyl, A.sup.31=H, A.sup.32=H], [2712; Q=Q.sup.s3, A.sup.28=cyclopropyl, A.sup.29=H, A.sup.30=H, A.sup.31=H, A.sup.32=cyclopropyl], [2713; Q=Q.sup.s3, A.sup.28=H, A.sup.29=OCHF.sub.2, A.sup.30=H, A.sup.31=H, A.sup.32=H], [2714; Q=Q.sup.s1, A.sup.28=H, A.sup.29=H, A.sup.30=OCHF.sub.2, A.sup.31=H, A.sup.32=H], [2715; Q=Q.sup.s1, A.sup.28=H, A.sup.29=OCF.sub.3, A.sup.30=H, A.sup.31=H, A.sup.32=H], [2716; Q=Q.sup.s3, A.sup.28=H, A.sup.29=H, A.sup.30=OCF.sub.3, A.sup.31=H, A.sup.32=H], [2717; Q=Q.sup.s3, A.sup.33=H, A.sup.34=H, A.sup.35=H], [2718; Q=Q.sup.s4, A.sup.33=Me, A.sup.34=H, A.sup.35=H], [2719; Q=Q.sup.s4, A.sup.33=H, A.sup.34=Me, A.sup.35=H], [2720; Q=Q.sup.s4, A.sup.33=H, A.sup.34=H, A.sup.35=Me], [2721; Q=Q.sup.s4, A.sup.33=Me, A.sup.34=Me, A.sup.35=H], [2722; Q=Q.sup.s4, A.sup.33=Me, A.sup.34=H, A.sup.35=Me], [2723; Q=Q.sup.s4, A.sup.33=H, A.sup.34=Me, A.sup.35=Me], [2724; Q=Q.sup.s4, A.sup.33=Me, A.sup.34=Me, A.sup.35=Me], [2725; Q=Q.sup.s4, A.sup.33=H, A.sup.34=H, A.sup.35=Cl], [2726; Q=Q.sup.s4, A.sup.33=H, A.sup.34=H, A.sup.35=CF.sub.3], [2727; Q=Q.sup.s4, A.sup.33=H, A.sup.34=H, A.sup.35=OMe], [2728; Q=Q.sup.s5, A.sup.33=H, A.sup.34=H, A.sup.36=H], [2729; Q=Q.sup.s1, A.sup.33=Me, A.sup.34=H, A.sup.36=H], [2730; Q=Q.sup.s5, A.sup.33=H, A.sup.34=Me, A.sup.36=H], [2731; Q=Q.sup.q5, A.sup.33=H, A.sup.34=H, A.sup.36=Me], [2732; Q=Q.sup.s5, A.sup.33=Me, A.sup.34=Me, A.sup.36=H], [2733; Q=Q.sup.s5, A.sup.33=Me, A.sup.34=H, A.sup.36=Me], [2734; Q=Q.sup.s5, A.sup.33=H, A.sup.34=Me, A.sup.36=Me], [2735; Q=Q.sup.s5, A.sup.33=Me, A.sup.34=Me, A.sup.36=Me], [2736; Q=Q.sup.s5, A.sup.33=H, A.sup.34=Cl, A.sup.36=H], [2737; Q=Q.sup.q5, A.sup.33=H, A.sup.34=CF.sub.3, A.sup.36=H], [2738; Q=Q.sup.s5, A.sup.33=H, A.sup.34=OMe, A.sup.36=H], [2739; Q=Q.sup.s5, A.sup.33=H, A.sup.34=H, A.sup.36=Cl], [2740; Q=Q.sup.s5, A.sup.33=H, A.sup.34=H, A.sup.36=CF.sub.3], [2741; Q=Q.sup.s1, A.sup.33=H, A.sup.34=H, A.sup.36=OMe], [2742; Q=Q.sup.t1, A.sup.37=H, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=H], [2743; Q=Q.sup.t1, A.sup.37=Cl, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=H], [2744; Q=Q.sup.t1, A.sup.37=H, A.sup.38=Cl, A.sup.39=H, A.sup.40=H, A.sup.41=H], [2745; Q=Q.sup.t1, A.sup.37=H, A.sup.38=H, A.sup.39=Cl, A.sup.40=H, A.sup.41=H], [2746; Q=Q.sup.t1, A.sup.37=Cl, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=Cl], [2747; Q=Q.sup.t1, A.sup.37=H, A.sup.38=Cl, A.sup.39=H, A.sup.40=Cl, A.sup.41=H], [2748; Q=Q.sup.t1, A.sup.37=Me, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=H], [2749; Q=Q.sup.t1, A.sup.37=H, A.sup.38=Me, A.sup.39=H, A.sup.40=H, A.sup.41=H], [2750; Q=Q.sup.t1, A.sup.37=H, A.sup.38=H, A.sup.39=Me, A.sup.40=H, A.sup.41=H], [2751; Q=Q.sup.t1, A.sup.37=Me, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=Me], [2752; Q=Q.sup.t1, A.sup.37=H, A.sup.38=Me, A.sup.39=H, A.sup.40=Me, A.sup.41=H], [2753; Q=Q.sup.t1, A.sup.37=H, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=H], [2754; Q=Q.sup.t2, A.sup.37=H, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=H], [2755; Q=Q.sup.t2, A.sup.37=Cl, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=H], [2756; Q=Q.sup.t2, A.sup.37=H, A.sup.38=Cl, A.sup.39=H, A.sup.40=H, A.sup.41=H], [2757; Q=Q.sup.t2, A.sup.37=H, A.sup.38=H, A.sup.39=Cl, A.sup.40=H, A.sup.41=H], [2758; Q=Q.sup.t2, A.sup.37=Cl, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=Cl], [2759; Q=Q.sup.t2, A.sup.37=H, A.sup.38=Cl, A.sup.39=H, A.sup.40=Cl, A.sup.41=H], [2760; Q=Q.sup.t2, A.sup.37=Me, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=H], [2761; Q=Q.sup.t2, A.sup.37=H, A.sup.38=Me, A.sup.39=H, A.sup.40=H, A.sup.41=H], [2762; Q=Q.sup.t2, A.sup.37=H, A.sup.38=H, A.sup.39=Me, A.sup.40=H, A.sup.41=H], [2763; Q=Q.sup.t2, A.sup.37=Me, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=Me], [2764; Q=Q.sup.t2, A.sup.37=H, A.sup.38=Me, A.sup.39=H, A.sup.40=Me, A.sup.41=H], [2765; Q=Q.sup.t2, A.sup.37=H, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=H], [2766; Q=Q.sup.t3, A.sup.37=H, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=H], [2767; Q=Q.sup.t3, A.sup.37=Cl, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=H], [2768; Q=Q.sup.t3, A.sup.37=H, A.sup.38=Cl, A.sup.39=H, A.sup.40=H, A.sup.41=H], [2769; Q=Q.sup.t3, A.sup.37=H, A.sup.38=H, A.sup.39=Cl, A.sup.40=H, A.sup.41=H], [2770; Q=Q.sup.t3, A.sup.37=Cl, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=Cl], [2771; Q=Q.sup.t3, A.sup.37=H, A.sup.38=Cl, A.sup.39=H, A.sup.40=Cl, A.sup.1=H], [2772; Q=Q.sup.t3, A.sup.37=Me, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=H], [2773; Q=Q.sup.t3, A.sup.37=H, A.sup.38=Me, A.sup.39=H, A.sup.40=H, A.sup.41=H], [2774; Q=Q.sup.t3, A.sup.37=H, A.sup.38=H, A.sup.39=Me, A.sup.40=H, A.sup.41=H], [2775; Q=Q.sup.t3, A.sup.37=Me, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=Me], [2776; Q=Q.sup.t3, A.sup.37=H, A.sup.38=Me, A.sup.39=H, A.sup.40=Me, A.sup.41=H], [2777; Q=Q.sup.t3, A.sup.37=H, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=H], [2778; Q=Q.sup.t4, A.sup.37=H, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=H], [2779; Q=Q.sup.t4, A.sup.37=Cl, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=H], [2780; Q=Q.sup.t4, A.sup.37=H, A.sup.38=Cl, A.sup.39=H, A.sup.40=H, A.sup.41=H], [2781; Q=Q.sup.t4, A.sup.37=H, A.sup.38=H, A.sup.39=Cl, A.sup.40=H, A.sup.49=H], [2782; Q=Q.sup.t4, A.sup.37=Cl, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=Cl], [2783; Q=Q.sup.t4, A.sup.37=H, A.sup.38=Cl, A.sup.39=H, A.sup.40=Cl, A.sup.41=H], [2784; Q=Q.sup.t4, A.sup.37=Me, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=H], [2785; Q=Q.sup.t4, A.sup.37=H, A.sup.38=Me, A.sup.39=H, A.sup.40=H, A.sup.41=H], [2786; Q=Q.sup.t4, A.sup.37=H, A.sup.38=H, A.sup.39=Me, A.sup.40=H, A.sup.41=H], [2787; Q=Qt, A.sup.37=Me, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=Me], [2788; Q=Q.sup.t4, A.sup.37=H, A.sup.38=Me, A.sup.39=H, A.sup.40=Me, A.sup.41=H], [2789; Q=Q.sup.t4, A.sup.37=H, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=H], [2790; Q=Q.sup.t5, A.sup.37=H, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=H], [2791; Q=Q.sup.t5, A.sup.37=Cl, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=H], [2792; Q=Q.sup.t5, A.sup.37=H, A.sup.38=Cl, A.sup.39=H, A.sup.40=H, A.sup.41=H], [2793; Q=Q.sup.t5, A.sup.37=H, A.sup.38=H, A.sup.39=Cl, A.sup.40=H, A.sup.41=H], [2794; Q=Q.sup.t5, A.sup.37=Cl, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=Cl], [2795; Q=Q.sup.t5, A.sup.37=H, A.sup.38=Cl, A.sup.39=H, A.sup.40=Cl, A.sup.41=H], [2796; Q=Q.sup.t5, A.sup.37=Me, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=H], [2797; Q=Q.sup.t5, A.sup.37=H, A.sup.38=Me, A.sup.39=H, A.sup.40=H, A.sup.41=H], [2798; Q=Q.sup.t5, A.sup.37=H, A.sup.38=H, A.sup.39=Me, A.sup.40=H, A.sup.41=H], [2799; Q=Q.sup.t5, A.sup.37=Me, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=Me], [2800; Q=Q.sup.t5, A.sup.37=H, A.sup.38=Me, A.sup.39=H, A.sup.40=Me, A.sup.41=H], [2801; Q=Q.sup.t5, A.sup.37=H, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=H], [2802; Q=Q.sup.t6, A.sup.37=H, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=H], [2803; Q=Q.sup.t6, A.sup.37=Cl, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=H], [2804; Q=Q.sup.t6, A.sup.37=H, A.sup.38=Cl, A.sup.39=H, A.sup.40=H, A.sup.41=H], [2805; Q=Q.sup.t6, A.sup.37=H, A.sup.38=H, A.sup.39=Cl, A.sup.40=H, A.sup.41=H], [2806; Q=Q.sup.t6, A.sup.37=Cl, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=Cl], [2807; Q=Q.sup.t6, A.sup.37=H, A.sup.38=Cl, A.sup.39=H, A.sup.40=Cl, A.sup.41=H], [2808; Q=Q.sup.t6, A.sup.37=Me, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=H], [2809; Q=Q.sup.t6, A.sup.37=H, A.sup.38=Me, A.sup.39=H, A.sup.40=H, A.sup.41=H], [2810; Q=Q.sup.t6, A.sup.37=H, A.sup.38=H, A.sup.39=Me, A.sup.40=H, A.sup.41=H], [2811; Q=Q.sup.t6, A.sup.37=Me, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=Me], [2812; Q=Q.sup.t6, A.sup.37=H, A.sup.38=Me, A.sup.39=H, A.sup.40=Me, A.sup.41=H], [2813; Q=Q.sup.t6, A.sup.37=H, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=H], [2814; Q=Q.sup.t7, A.sup.37=H, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=H, A.sup.42=H], [2815; Q=Q.sup.t7, A.sup.37=Cl, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=H, A.sup.42=H], [2816; Q=Q.sup.t7, A.sup.37=H, A.sup.38=Cl, A.sup.39=H, A.sup.40=H, A.sup.41=H, A.sup.42=H], [2817; Q=Q.sup.t7, A.sup.37=H, A.sup.38=H, A.sup.39=Cl, A.sup.40=H, A.sup.41=H, A.sup.42=H], [2818; Q=Q.sup.t7, A.sup.37=Cl, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=Cl, A.sup.42=H], [2819; Q=Q.sup.t7, A.sup.37=H, A.sup.38=Cl, A.sup.39=H, A.sup.40=Cl, A.sup.41=H, A.sup.42=H], [2820; Q=Q.sup.t7, A.sup.37=Me, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=H, A.sup.42=H], [2821; Q=Q.sup.t7, A.sup.37=H, A.sup.38=Me, A.sup.39=H, A.sup.40=H, A.sup.41=H, A.sup.42=H], [2822; Q=Q.sup.t7, A.sup.37=H, A.sup.38=H, A.sup.39=Me, A.sup.40=H, A.sup.41=H, A.sup.42=H], [2823; Q=Q.sup.t7, A.sup.37=Me, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=Me, A.sup.42=H], [2824; Q=Q.sup.t7, A.sup.37=H, A.sup.38=Me, A.sup.39=H, A.sup.40=Me, A.sup.4=H, A.sup.42=H], [2825; Q=Q.sup.t7, A.sup.37=H, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=H, A.sup.42=Me], [2826; Q=Q.sup.t7, A.sup.37=H, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=H, A.sup.42=Me], [2827; Q=Q.sup.t7, A.sup.37=Cl, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=H, A.sup.42=Me], [2828; Q=Q.sup.t7, A.sup.37=H, A.sup.38=Cl, A.sup.39=H, A.sup.40=H, A.sup.41=H, A.sup.42=Me], [2829; Q=Q.sup.t7, A.sup.37=H, A.sup.38=H, A.sup.39=Cl, A.sup.40=H, A.sup.41=H, A.sup.42=Me], [2830; Q=Q.sup.t7, A.sup.37=Cl, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=Cl, A.sup.42=Me], [2831; Q=Q.sup.t7, A.sup.37=H, A.sup.38=Cl, A.sup.39=H, A.sup.40=Cl, A.sup.4=H, A.sup.42=Me], [2832; Q=Q.sup.t7, A.sup.37=Me, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=H, A.sup.42=Me], [2833; Q=Q.sup.t7, A.sup.37=H, A.sup.38=Me, A.sup.39=H, A.sup.40=H, A.sup.41=H, A.sup.42=Me], [2834; Q=Q.sup.t7, A.sup.37=H, A.sup.38=H, A.sup.39=Me, A.sup.40=H, A.sup.41=H, A.sup.42=Me], [2835; Q=Q.sup.t7, A.sup.37=Me, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=Me, A.sup.42=Me], [2836; Q=Q.sup.t7, A.sup.37=H, A.sup.38=Me, A.sup.39=H, A.sup.40=Me, A.sup.41=H, A.sup.42=Me], [2837; Q=Q.sup.t7, A.sup.37=H, A.sup.38=H, A.sup.39=H, A.sup.40=H, A.sup.41=H, A.sup.42=Me], [2838; Q=Q.sup.v1, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=H][2839; Q=Q.sup.v1, R.sup.29=F, R.sup.30=H, R.sup.31=H, R.sup.32=H], [2840; Q=Q.sup.v1, R.sup.29=H, R.sup.30=F, R.sup.31=H, R.sup.32=H], [2841; Q=Q.sup.v1, R.sup.29=H, R.sup.30=H, R.sup.31=F, R.sup.32=H], [2842; Q=Q.sup.v1, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=F], [2843; Q=Q.sup.v1, R.sup.29=Cl, R.sup.30=H, R.sup.31=H, R.sup.32=H], [2844; Q=Q.sup.v1, R.sup.29=H, R.sup.30=Cl, R.sup.31=H, R.sup.32=H], [2845; Q=Q.sup.v1, R.sup.29=H, R.sup.30=H, R.sup.31=Cl, R.sup.32=H], [2846; Q=Q.sup.v1, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=Cl], [2847; Q=Q.sup.v1, R.sup.29=Me, R.sup.30=H, R.sup.31=H, R.sup.32=H], [2848; Q=Q.sup.v1, R.sup.29=H, R.sup.30=Me, R.sup.31=H, R.sup.32=H], [2849; Q=Q.sup.v1, R.sup.29=H, R.sup.30=H, R.sup.31=Me, R.sup.32=H], [2850; Q=Q.sup.v1, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=Me], [2851; Q=Q.sup.v1, R.sup.29=OMe, R.sup.30=H, R.sup.31=H, R.sup.32=H], [2852; Q=Q.sup.v1, R.sup.29=H, R.sup.30=OMe, R.sup.31=H, R.sup.32=H], [2853; Q=Q.sup.v1, R.sup.29=H, R.sup.30=H, R.sup.31=OMe, R.sup.32=H], [2854; Q=Q.sup.v1, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=OMe], [2855; Q=Q.sup.v1, R.sup.29=CF.sub.3, R.sup.30=H, R.sup.31=H, R.sup.32=H][2856; Q=Q.sup.v1, R.sup.29=H, R.sup.30=CF.sub.3, R.sup.31=H, R.sup.32=H], [2857; Q=Q.sup.v1, R.sup.29=H, R.sup.30=H, R.sup.31=CF.sub.3, R.sup.32=H], [2858; Q=Q.sup.v1, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=CF.sub.3], [2859; Q=Q.sup.v2, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=H], [2860; Q=Q.sup.v2, R.sup.29=F, R.sup.30=H, R.sup.31=H, R.sup.32=H], [2861; Q=Q.sup.v2, R.sup.29=H, R.sup.30=F, R.sup.31=H, R.sup.32=H], [2862; Q=Q.sup.v2, R.sup.29=H, R.sup.30=H, R.sup.31=F, R.sup.32=H], [2863; Q=Q.sup.v2, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=F], [2864; Q=Q.sup.v2, R.sup.29=Cl, R.sup.30=H, R.sup.31=H, R.sup.32=H], [2865; Q=Q.sup.v2, R.sup.29=H, R.sup.30=Cl, R.sup.31=H, R.sup.32=H], [2866; Q=Q.sup.v2, R.sup.29=H, R.sup.30=H, R.sup.31=Cl, R.sup.32=H], [2867; Q=Q.sup.v2, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=Cl], [2868; Q=Q.sup.v2, R.sup.29=Me, R.sup.30=H, R.sup.31=H, R.sup.32=H], [2869; Q=Q.sup.q2, R.sup.29=H, R.sup.30=Me, R.sup.31=H, R.sup.32=H], [2870; Q=Q.sup.v2, R.sup.29=H, R.sup.30=H, R=Me, R.sup.32=H], [2871; Q=Q.sup.v2, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=Me], [2872; Q=Q.sup.v2, R.sup.29=Me, R.sup.30=H, R.sup.31=H, R.sup.32=H], [2873; Q=Q.sup.v2, R.sup.29=H, R.sup.30=OMe, R.sup.31=H, R.sup.32=H], [2874; Q=Q.sup.v2, R.sup.29=H, R.sup.30=H, R.sup.31=Me, R.sup.32=H], [2875; Q=Q.sup.v2, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=OMe], [2876; Q=Q.sup.v2, R.sup.29=CF.sub.3, R.sup.30=H, R.sup.31=H, R.sup.32=H], [2877; Q=Q 29=H, R.sup.29=H, R.sup.30=CF.sub.3, R.sup.31=H, R.sup.32=H], [2878; Q=Q.sup.v2, R.sup.29=H, R.sup.30=H, R.sup.31=CF.sub.3, R.sup.32=H], [2879; Q=Q.sup.v2, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=CF.sub.3], [2880; Q=Q.sup.v3, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=H], [2881; Q=Q.sup.v3, R.sup.29=F, R.sup.30=H, R.sup.31=H, R.sup.32=H][2882; Q=Q.sup.v3, R.sup.29=H, R.sup.30=F, R.sup.31=H, R.sup.32=H], [2883; Q=Q.sup.v3, R.sup.29=H, R.sup.30=H, R.sup.31=F, R.sup.32=H], [2884; Q=Q.sup.v3, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=F], [2885; Q=Q.sup.v3, R.sup.29=Cl, R.sup.30=H, R.sup.31=H, R.sup.32=H], [2886; Q=Q.sup.v3, R.sup.29=H, R.sup.30=Cl, R.sup.31=H, R.sup.32=H], [2887; Q=Q.sup.v3, R.sup.29=H, R.sup.30=H, R.sup.31=Cl, R.sup.32=H], [2888; Q=Q.sup.v3, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=Cl], [2889; Q=Q.sup.v3, R.sup.29=Me, R.sup.30=H, R.sup.31=H, R.sup.32=H], [2890; Q=Q.sup.v3, R.sup.29=H, R.sup.30=Me, R.sup.31=H, R.sup.32=H], [2891; Q=Q.sup.v3, R.sup.29=H, R.sup.30=H, R.sup.31=Me, R.sup.32=H], [2892; Q=Q.sup.v3, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=Me], [2893; Q=Q.sup.v3, R.sup.29=OMe, R.sup.30=H, R.sup.31=H, R.sup.32=H], [2894; Q=Q.sup.v3, R.sup.29=H, R.sup.30=OMe, R.sup.31=H, R.sup.32=H], [2895; Q=Q.sup.v3, R.sup.29=H, R.sup.30=H, R.sup.31=OMe, R.sup.32=H], [2896; Q=Q.sup.v3, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=OMe], [2897; Q=Q.sup.v3, R.sup.29=CF.sub.3, R.sup.30=H, R.sup.31=H, R.sup.32=H], [2898; Q=Q.sup.v3, R.sup.29=H, R.sup.30=CF.sub.3, R.sup.31=H, R.sup.32=H], [2899; Q=Q.sup.v3, R.sup.29=H, R.sup.30=H, R.sup.31=CF.sub.3, R.sup.32=H], [2900; Q=Q.sup.v3, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=CF.sub.3], [2901; Q=Q.sup.s1, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=H], [2902; Q=Q.sup.v4, R.sup.29=F, R.sup.30=H, R.sup.31=H, R.sup.32=H], [2903; Q=Q.sup.v4, R.sup.29=H, R.sup.30=F, R.sup.31=H, R.sup.32=H], [2904; Q=Q.sup.v4, R.sup.29=H, R.sup.30=H, R.sup.31=F, R.sup.32=H], [2905; Q=Q.sup.v4, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=F], [2906; Q=Q.sup.v4, R.sup.29=Cl, R.sup.30=H, R.sup.31=H, R.sup.32=H], [2907; Q=Q.sup.v4, R.sup.29=H, R.sup.30=Cl, R.sup.31=H, R.sup.32=H], [2908; Q=Q.sup.v4, R.sup.29=H, R.sup.30=H, R.sup.31=Cl, R.sup.32=H], [2909; Q=Q.sup.v4, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=Cl], [2910; Q=Q.sup.v4, R.sup.29=Me, R.sup.30=H, R.sup.31=H, R.sup.32=H], [2911; Q=Q.sup.v4, R.sup.29=H, R.sup.30=Me, R.sup.31=H, R.sup.32=H], [2912; Q=Q.sup.v4, R.sup.29=H, R.sup.30=H, R.sup.31=Me, R.sup.32=H], [2913; Q=Q.sup.v4, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=Me], [2914; Q=Q.sup.s1, R.sup.29=OMe, R.sup.30=H, R.sup.31=H, R.sup.32=H], [2915; Q=Q.sup.v4, R.sup.29=H, R.sup.30=OMe, R.sup.31=H, R.sup.32=H], [2916; Q=Q.sup.v4, R.sup.29=H, R.sup.30=H, R.sup.31=OMe, R.sup.32=H], [2917; Q=Q.sup.s1, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=OMe], [2918; Q=Q.sup.v4, R.sup.29=CF.sub.3, R.sup.30=H, R.sup.31=H, R.sup.32=H], [2919; Q=Q.sup.v4, R.sup.29=H, R.sup.30=CF.sub.3, R.sup.31=H, R.sup.32=H], [2920; Q=Q.sup.v4, R.sup.29=H, R.sup.30=H, R.sup.31=CF.sub.3, R.sup.32=H], [2921; Q=Q.sup.v4, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=CF.sub.3], [2922; Q=Q.sup.v5, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=H], [2923; Q=Q.sup.v5, R.sup.29=F, R.sup.30=H, R.sup.31=H, R.sup.32=H], [2924; Q=Q.sup.v5, R.sup.29=H, R.sup.30=F, R.sup.31=H, R.sup.32=H], [2925; Q=Q.sup.v5, R.sup.29=H, R.sup.30=H, R.sup.31=F, R.sup.32=H], [2926; Q=Q.sup.v5, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=F], [2927; Q=Q.sup.v5, R.sup.29=Cl, R.sup.30=H, R.sup.31=H, R.sup.32=H], [2928; Q=Q.sup.v5, R.sup.29=H, R.sup.30=Cl, R.sup.31=H, R.sup.32=H], [2929; Q=Q.sup.v5, R.sup.29=H, R.sup.30=H, R.sup.31=Cl, R.sup.32=H], [2930; Q=Q.sup.v5, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=C], [2931; Q=Q.sup.q5, R.sup.29=Me, R.sup.30=H, R.sup.31=H, R.sup.32=H], [2932; Q=Q.sup.v1, R.sup.29=H, R.sup.30=Me, R.sup.31=H, R.sup.32=H], [2933; Q=Q.sup.v5, R.sup.29=H, R.sup.30=H, R.sup.31=Me, R.sup.32=H], [2934; Q=Q.sup.v5, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=Me], [2935; Q=Q.sup.v5, R.sup.29=OMe, R.sup.30=H, R.sup.31=H, R.sup.32=H], [2936; Q=Q.sup.v5, R.sup.29=H, R.sup.30=OMe, R.sup.31=H, R.sup.32=H], [2937; Q=Q.sup.v5, R.sup.29=H, R.sup.30=H, R.sup.31=OMe, R.sup.32=H], [2938; Q=Q.sup.v5, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=OMe], [2939; Q=Q.sup.q5, R.sup.29=CF.sub.3, R.sup.30=H, R.sup.31=H, R.sup.32=H], [2940; Q=Q.sup.v5, R.sup.29=H, R.sup.30=CF.sub.3, R.sup.31=H, R.sup.32=H], [2941; Q=Q.sup.v5, R.sup.29=H, R.sup.30=H, R.sup.31=CF.sub.3, R.sup.32=H], [2942; Q=Q.sup.v5, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=CF.sub.3], [2943; Q=Q.sup.v6, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=H], [2944; Q=Q.sup.v6, R.sup.29=F, R.sup.30=H, R.sup.31=H, R.sup.32=H], [2945; Q=Q.sup.v6, R.sup.29=H, R.sup.30=F, R.sup.31=H, R.sup.32=H], [2946; Q=Q.sup.v6, R.sup.29=H, R.sup.30=H, R.sup.31=F, R.sup.32=H], [2947; Q=Q.sup.v1, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=F], [2948; Q=Q.sup.v6, R.sup.29=Cl, R.sup.30=H, R.sup.31=H, R.sup.32=H], [2949; Q=Q.sup.v6, R.sup.29=H, R.sup.30=Cl, R.sup.31=H, R.sup.32=H], [2950; Q=Q.sup.v6, R.sup.29=H, R.sup.30=H, R.sup.31=Cl, R.sup.32=H], [2951; Q=Q.sup.v6, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=Cl], [2952; Q=Q.sup.v6, R.sup.29=Me, R.sup.30=H, R.sup.31=H, R.sup.32=H], [2953; Q=Q.sup.v6, R.sup.29=H, R.sup.30=Me, R.sup.31=H, R.sup.32=H], [2954; Q=Q.sup.v6, R.sup.29=H, R.sup.30=H, R.sup.31=Me, R.sup.32=H], [2955; Q=Q.sup.v6, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=Me], [2956; Q=Q.sup.v6, R.sup.29=OMe, R.sup.30=H, R.sup.31=H, R.sup.32=H], [2957; Q=Q.sup.v6, R.sup.29=H, R.sup.30=OMe, R.sup.31=H, R.sup.32=H], [2958; Q=Q.sup.v6, R.sup.29=H, R.sup.30=H, R.sup.31=OMe, R.sup.32=H], [2959; Q=Q.sup.v6, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=OMe], [2960; Q=Q.sup.v6, R.sup.29=CF.sub.3, R.sup.30=H, R.sup.31=H, R.sup.32=H][2961; Q=Q.sup.v6, R.sup.29=H, R.sup.30=CF.sub.3, R.sup.31=H, R.sup.32=H], [2962; Q=Q.sup.v6, R.sup.29=H, R.sup.30=H, R.sup.31=CF.sub.3, R.sup.32=H], [2963; Q=Q.sup.v6, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=CF.sub.3], [2964; Q=Q.sup.v7, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=H], [2965; Q=Q.sup.v7, R.sup.29=F, R.sup.30=H, R.sup.31=H, R.sup.32=H], [2966; Q=Q.sup.v1, R.sup.29=H, R.sup.30=F, R.sup.31=H, R.sup.32=H], [2967; Q=Q.sup.v7, R.sup.29=H, R.sup.30=H, R.sup.31=F, R.sup.32=H], [2968; Q=Q.sup.v7, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=F], [2969; Q=Q.sup.v7, R.sup.29=Cl, R.sup.30=H, R.sup.31=H, R.sup.32=H], [2970; Q=Q.sup.v7, R.sup.29=H, R.sup.30=Cl, R.sup.31=H, R.sup.32=H], [2971; Q=Q.sup.v7, R.sup.29=H, R.sup.30=H, R.sup.31=Cl, R.sup.32=H], [2972; Q=Q.sup.v7, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=Cl], [2973; Q=Q.sup.v7, R.sup.29=Me, R.sup.30=H, R.sup.31=H, R.sup.32=H], [2974; Q=Q.sup.v7, R.sup.29=H, R.sup.30=Me, R.sup.31=H, R.sup.32=H], [2975; Q=Q.sup.v7, R.sup.29=H, R.sup.30=H, R=Me, R.sup.32=H], [2976; Q=Q.sup.v7, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=Me], [2977; Q=Q.sup.v7, R.sup.29=OMe, R.sup.30=H, R.sup.31=H, R.sup.32=H], [2978; Q=Q.sup.v7, R.sup.29=H, R.sup.30=OMe, R.sup.31=H, R.sup.32=H], [2979; Q=Q.sup.v7, R.sup.29=H, R.sup.30=H, R.sup.31=Me, R.sup.32=H], [2980; Q=Q.sup.v7, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=OMe], [2981; Q=Q.sup.v7, R.sup.29=CF.sub.3, R.sup.30=H, R.sup.31=H, R.sup.32=H], [2982; Q=Q.sup.v1, R.sup.29=H, R.sup.30=CF.sub.3, R.sup.31=H, R.sup.32=H], [2983; Q=Q.sup.v7, R.sup.29=H, R.sup.30=H, R.sup.31=CF.sub.3, R.sup.32=H], [2984; Q=Q.sup.v7, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=CF.sub.3], [2985; Q=Q.sup.v5, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=H], [2986; Q=Q.sup.v8, R.sup.29=F, R.sup.30=H, R.sup.31=H, R.sup.32=H], [2987; Q=Q.sup.v8, R.sup.29=H, R.sup.30=F, R.sup.31=H, R.sup.32=H], [2988; Q=Q.sup.v8, R.sup.29=H, R.sup.30=H, R.sup.31=F, R.sup.32=H], [2989; Q=Q.sup.v1, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=F], [2990; Q=Q.sup.v8, R.sup.29=Cl, R.sup.30=H, R.sup.31=H, R.sup.32=H], [2991; Q=Q.sup.v8, R.sup.29=H, R.sup.30=Cl, R.sup.31=H, R.sup.32=H], [2992; Q=Q.sup.v8, R.sup.29=H, R.sup.30=H, R.sup.31=Cl, R.sup.32=H], [2993; Q=Q.sup.v8, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=Cl], [2994; Q=Q.sup.v8, R.sup.29=Me, R.sup.30=H, R.sup.31=H, R.sup.32=H], [2995; Q=Q.sup.v8, R.sup.29=H, R.sup.30=Me, R.sup.31=H, R.sup.32=H], [2996; Q=Q.sup.v8, R.sup.29=H, R.sup.30=H, R.sup.31=Me, R.sup.32=H], [2997; Q=Q.sup.v8, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=Me], [2998; Q=Q.sup.v8, R.sup.29=OMe, R.sup.30=H, R.sup.31=H, R.sup.32=H][2999; Q=Q.sup.v8, R.sup.29=H, R.sup.30=OMe, R.sup.31=H, R.sup.32=H], [3000; Q=Q.sup.v8, R.sup.29=H, R.sup.30=H, R.sup.31=OMe, R.sup.32=H], [3001; Q=Q.sup.v8, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=OMe], [3002; Q=Q.sup.v8, R.sup.29=CF.sub.3, R.sup.30=H, R.sup.31=H, R.sup.32=H], [3003; Q=Q.sup.v8, R.sup.29=H, R.sup.30=CF.sub.3, R.sup.31=H, R.sup.32=H], [3004; Q=Q.sup.v8, R.sup.29=H, R.sup.30=H, R.sup.31=CF.sub.3, R.sup.32=H], [3005; Q=Q.sup.v8, R.sup.29=H, R.sup.30=H, R.sup.31=H, R.sup.32=CF.sub.3], [3006; Q=Q.sup.v8, A.sup.42=H, A.sup.43=H, A.sup.44=H, A.sup.45=H, A.sup.46=H, A.sup.47=H, A.sup.48=H, A.sup.49=H], [3007; Q=Q.sup.v9, A.sup.42=F, A.sup.43=H, A.sup.44=H, A.sup.45=H, A.sup.6=H, A.sup.47=H, A.sup.8=H, A.sup.49=H], [3008; Q=Q.sup.v9, A.sup.42=H, A.sup.43=H, A.sup.44=F, A.sup.45=H, A.sup.46=H, A.sup.47=H, A.sup.48=H, A.sup.49=H], [3009; Q=Q.sup.v9, A.sup.42=H, A.sup.43=H, A.sup.44=H, A.sup.45=H, A.sup.46=F, A.sup.47=H, A.sup.48=H, A.sup.49=H], [3010; Q=Q.sup.v9, A.sup.42=H, A.sup.43=H, A.sup.44=H, A.sup.45=H, A.sup.46=H, A.sup.47=H, A.sup.48=F, A.sup.49=H], [3011; Q=Q.sup.v9, A.sup.42=Cl, A.sup.43=H, A.sup.44=H, A.sup.45=H, A.sup.46=H, A.sup.47=H, A.sup.48=H, A.sup.49=H], [3012; Q=Q.sup.v9, A.sup.42=H, A.sup.43=H, A.sup.44=Cl, A.sup.45=H, A.sup.46=H, A.sup.47=H, A.sup.48=H, A.sup.49=H], [3013; Q=Q.sup.r9, A.sup.42=H, A.sup.43=H, A.sup.44=H, A.sup.45=H, A.sup.46=Cl, [A.sup.47=H, A.sup.48=H, A.sup.49=H], [3014; Q=Q.sup.v9, A.sup.42=H, A.sup.43=H, A.sup.44=H, A.sup.45=H, A.sup.46=H, A.sup.47=H, A.sup.48=Cl, A.sup.49=H], [3015; Q=Q.sup.v9, A.sup.42=Me, A.sup.43=H, A.sup.44=H, A.sup.45=H, A.sup.46=H, A.sup.47=H, A.sup.48=H, A.sup.49=H], [3016; Q=Q.sup.v9, A.sup.42=H, A.sup.43=H, A.sup.44=Me, A.sup.45=H, A.sup.46=H, A.sup.47=H, A.sup.48=H, A.sup.49=H], [3017; Q=Q.sup.v9, A.sup.42=H, A.sup.13=H, A.sup.44=H, A.sup.45=H, A.sup.46=Me, A.sup.47=H, A.sup.48=H, A.sup.49=H], [3018; Q=Q.sup.v9, A.sup.42=H, A.sup.43=H, A.sup.44=H, A.sup.45=H, A.sup.46=H, A.sup.47=H, A.sup.48=Me, A.sup.49=H], [3019; Q=Q.sup.v9, A.sup.42=OMe, A.sup.43=H, A.sup.44=H, A.sup.45=H, A.sup.46=H, A.sup.47=H, A.sup.48=H, A.sup.49=H], [3020; Q=Q.sup.v9, A.sup.42=H, A.sup.43=H, A.sup.44=OMe, A.sup.45=H, A.sup.46=H, A.sup.47=H, A.sup.48=H, A.sup.49=H], [3021; Q=Q.sup.v9, A.sup.2=H, A.sup.43=H, A.sup.44=H, A.sup.45=H, A.sup.46=OMe, A.sup.47=H, A.sup.48=H, A.sup.49=H], [3022; Q=Q.sup.r9, A.sup.42=H, A.sup.43=H, A.sup.44=H, A.sup.45=H, A.sup.46=H, A.sup.47=H, A.sup.48=OMe, A.sup.49=H], [3023; Q=Q.sup.v9, A.sup.42=CF.sub.3, A.sup.43=H, A.sup.44=H, A.sup.45=H, A.sup.46=H, A.sup.47=H, A.sup.48=H, A.sup.9=H], [3024; Q=Q.sup.v9, A.sup.42=H, A.sup.43=H, A.sup.44=CF.sub.3, A.sup.45=H, A.sup.46=H, A.sup.47=H, A.sup.48=H, A.sup.49=H], [3025; Q=Q.sup.v9, A.sup.42=H, A.sup.43=H, A.sup.44=H, A.sup.45=H, A.sup.46=CF.sub.3, A.sup.47=H, A.sup.48=H, A.sup.49=H], [3026; Q=Q.sup.v9, A.sup.42=H, A.sup.43=H, A.sup.1=H, A.sup.45=H, A.sup.46=H, A.sup.47=H, A.sup.48=CF.sub.3, A.sup.49=H], [3027; Q=Q.sup.v9, A.sup.42=F, A.sup.43=F, A.sup.44=H, A.sup.45=H, A.sup.46=H, A.sup.47=H, A.sup.48=H, A.sup.49=H], [3028; Q=Q.sup.v9, A.sup.42=H, A.sup.43=H, A.sup.44=F, A.sup.45=F, A.sup.46=H, A.sup.47=H, A.sup.48=H, A.sup.49=H], [3029; Q=Q.sup.v9, A.sup.42=H, A.sup.43=H, A.sup.44=H, A.sup.45=H, A.sup.46=F, A.sup.47=F, A.sup.48=H, A.sup.4=H], [3030; Q=Q.sup.v1, A.sup.42=H, A.sup.43=H, A.sup.44=H, A.sup.45=H, A.sup.46=H, A.sup.47=H, A.sup.48=F, A.sup.49=F], [3031; Q=Q.sup.v10, A.sup.42=H, A.sup.43=H, A.sup.44=H, A.sup.45=H, A.sup.46=H, A.sup.47=H, A.sup.48=H, A.sup.49=H], [3032; Q=Q.sup.v10, A.sup.42=F, A.sup.43=H, A.sup.44=H, A.sup.45=H, A.sup.46=H, A.sup.47=H, A.sup.48=H, A.sup.49=H], [3033; Q=Q.sup.v10, A.sup.42=H, A.sup.43=H, A.sup.44=F, A.sup.45=H, A.sup.46=H, A.sup.47=H, A.sup.48=H, A.sup.1=H], [3034; Q=Q.sup.v10, A.sup.42=H, A.sup.43=H, A.sup.44=H, A.sup.45=H, A.sup.46=F, A.sup.47=H, A.sup.48=H, A.sup.49=H], [3035; Q=Q.sup.v10, A.sup.42=H, A.sup.43=H, A.sup.44=H, A.sup.45=H, A.sup.46=H, A.sup.47=H, A.sup.48=F, A.sup.49=H], [3036; Q=Q.sup.v10, A.sup.42=Cl, A.sup.43=H, A.sup.44=H, A.sup.45=H, A.sup.46=H, A.sup.47=H, A.sup.48=H, A.sup.49=H], [3037; Q=Q.sup.v10, A.sup.42=H, A.sup.43=H, A.sup.44=Cl, A.sup.45=H, A.sup.46=H, A.sup.47=H, A.sup.48=H, A.sup.49=H], [3038; Q=Q.sup.v10, A.sup.42=H, A.sup.43=H, A.sup.44=H, A.sup.45=H, A.sup.46=Cl, A.sup.47=H, A.sup.48=H, A.sup.49=H], [3039; Q=Q.sup.v10, A.sup.42=H, A.sup.43=H, A.sup.44=H, A.sup.45=H, A.sup.46=H, A.sup.47=H, A.sup.48=Cl, A.sup.49=H], [3040; Q=Q.sup.v10, A.sup.42=Me, A.sup.43=H, A.sup.44=H, A.sup.45=H, A.sup.46=H, A.sup.47=H, A.sup.48=H, A.sup.49=H], [3041; Q=Q.sup.v10, A.sup.42=H, A.sup.43=H, A.sup.44=Me, A.sup.45=H, A.sup.46=H, A.sup.47=H, A.sup.48=H, A.sup.49=H], [3042; Q=Q.sup.v10, A.sup.42=H, A.sup.43=H, A.sup.44=H, A.sup.45=H, A.sup.46=Me, A.sup.47=H, A.sup.48=H, A.sup.49=H], [3043; Q=Q.sup.v10, A.sup.42=H, A.sup.43=H, A.sup.44=H, A.sup.45=H, A.sup.46=H, A.sup.47=H, A.sup.48=Me, A.sup.49=H], [3044; Q=Q.sup.v10, A.sup.42=OMe, A.sup.43=H, A.sup.44=H, A.sup.45=H, A.sup.46=H, A.sup.47=H, A.sup.48=H, A.sup.49=H], [3045; Q=Q.sup.v10, A.sup.42=H, A.sup.43=H, A.sup.44=OMe, A.sup.45=H, A.sup.46=H, A.sup.47=H, A.sup.48=H, A.sup.49=H], [3046; Q=Q.sup.v10, A.sup.42=H, A.sup.43=H, A.sup.44=H, A.sup.45=H, A.sup.46=OMe, A.sup.47=H, A.sup.48=H, A.sup.49=H], [3047; Q=Q.sup.v10, A.sup.42=H, A.sup.43=H, A.sup.44=H, A.sup.45=H, A.sup.46=H, A.sup.47=H, A.sup.48=OMe, A.sup.49=H], [3048; Q=Q.sup.v10, A.sup.42=CF.sub.3, A.sup.43=H, A.sup.44=H, A.sup.45=H, A.sup.46=H, A.sup.47=H, A.sup.48=H, A.sup.4=H], [3049; Q=Q.sup.v10, A.sup.42=H, A.sup.4=H, A.sup.44CF.sub.3, A.sup.45=H, A.sup.46=H, A.sup.47=H, A.sup.48=H, A.sup.49=H], [3050; Q=Q.sup.v10, A.sup.42=H, A.sup.43=H, A.sup.44=H, A.sup.45=H, A.sup.46=H, A.sup.47=H, A.sup.48=H, A.sup.49=H], [3051; Q=Q.sup.v10, A.sup.42=H, A.sup.43=H, A.sup.44=H, A.sup.45=H, A.sup.46=H, A.sup.47=H, A.sup.48=CF.sub.3, A.sup.49=H], [3052; Q=Q.sup.v10, A.sup.42=F, A.sup.43=F, A.sup.44=H, A.sup.45=H, A.sup.46=H, A.sup.47=H, A.sup.48=H, A.sup.49=H], [3053; Q=Q.sup.v10, A.sup.42=H, A.sup.43=H, A.sup.44=F, A.sup.45=F, A.sup.46=H, A.sup.47=H, A.sup.48=H, A.sup.49=H], [3054; Q=Q.sup.v10, A.sup.42=H, A.sup.43=H, A.sup.44=H, A.sup.45=H, A.sup.46=F, A.sup.47=F, A.sup.48=H, A.sup.49=H], and [3055; Q=Q.sup.v10, A.sup.42=H, A.sup.43=H, A.sup.44=H, A.sup.45=H, A.sup.46=H, A.sup.47=H, A.sup.48=F, A.sup.49=F]

(1273) According to the above method, it is possible to obtain compounds EC1B-5001 to EO7C-5107:

(1274) ##STR00589## ##STR00590## ##STR00591## ##STR00592## ##STR00593## ##STR00594## ##STR00595## ##STR00596## ##STR00597## ##STR00598## ##STR00599## ##STR00600## ##STR00601## ##STR00602## ##STR00603## ##STR00604## ##STR00605## ##STR00606## ##STR00607## ##STR00608## ##STR00609## ##STR00610## ##STR00611## ##STR00612##
wherein Q represents any one of substituent numbers 5001 to 5107, and Q.sup.P1 to Q.sup.p10 represent any one of the followings.

(1275) ##STR00613##

(1276) The substituent numbers 5001 to 5107 will be shown below.

(1277) Here, Me, OCF.sub.3, OMe, OCHF.sub.2, OCF.sub.3, and SMe are as defined above, CHF.sub.2 represents a difluoromethyl group, NO.sub.2 represents a nitro group, CN represents a cyano group, SCF.sub.3 represents a trifluoromethylthio group and, for example, [5001; Q=Q.sup.p1, R.sup.1L=H, R.sup.2L=H, R.sup.3L=H, R.sup.11L=H, R.sup.12L=H] represents a group in which Q is Q.sup.p1, and R.sup.1L, R.sup.2L, R.sup.3L, R.sup.11L, and R.sup.12L are hydrogen atoms, and a compound in which the substituent number is 5001 in EC1B represents the following compound.

(1278) ##STR00614##
[substituent number; Q], [5001; Q=Q.sup.p1, R.sup.1L=H, R.sup.2L=H, R.sup.3L=H, R.sup.11L=H, R.sup.12L=H], [5002; Q=Q.sup.p1, R.sup.1L=F, R.sup.2L=H, R.sup.3L=H, R.sup.1L=H, R.sup.12L=H], [5003; Q=Q.sup.p1, R.sup.1L=H, R.sup.2L=F, R.sup.3L=H, R.sup.11L=H, R.sup.12L=H], [5004; Q=Q.sup.p1, R.sup.1L=H, R.sup.2L=H, R.sup.3L=F, R.sup.11L=H, R.sup.12L=H], [5005; Q=Q.sup.p1, R.sup.1L=H, R.sup.2L=Cl, R.sup.3L=H, R.sup.11L=H, R.sup.12L=H], [5006; Q=Q.sup.p1, R.sup.1L=H, R.sup.2L=H, R.sup.3L=Cl, R.sup.11L=H, R.sup.12L=H], [5007; Q=Q.sup.p1, R.sup.1L=Me, R.sup.2L=H, R.sup.3L=H, R.sup.11L=H, R.sup.12L=H], [5008; Q=Q.sup.p1, R.sup.1L=H, R.sup.2L=Me, R.sup.3L=H, R.sup.11L=H, R.sup.12L=H], [5009; Q=Q.sup.p1, R.sup.1L=H, R.sup.2L=H, R.sup.3L=Me, R.sup.11L=H, R.sup.12L=H], [5010; Q=Q.sup.p1, R.sup.1L=H, R.sup.2L=CHF.sub.2, R.sup.3L=H, R.sup.11L=H, R.sup.12L=H], [5011; Q=Q.sup.p1, R.sup.1L=H, R.sup.2L=H, R.sup.3L=CHF.sub.2, R.sup.11L=H, R.sup.12L=H], [5012; Q=Q.sup.p1, R.sup.1L=H, R.sup.2L=CF.sub.3, R.sup.3L=H, R.sup.11L=H, R.sup.12L=H], [5013; Q=Q.sup.p1, R.sup.1L=H, R.sup.2L=H, R.sup.3L=CF.sub.3, R.sup.11L=H, R.sup.12L=H], [5014; Q=Q.sup.p1, R.sup.1L=H, R.sup.2L=Me, R.sup.3L=H, R.sup.11L=H, R.sup.12L=H], [5015; Q=Q.sup.p1, R.sup.1L=H, R.sup.2L=H, R.sup.3L=OMe, R.sup.11L=H, R.sup.12L=H], [5016; Q=Q.sup.p1, R.sup.1L=H, R.sup.2L=OCHF.sub.2, R.sup.3L=H, R.sup.11L=H, R.sup.12L=H], [5017; Q=Q.sup.p1, R.sup.1L=H, R.sup.2L=H, R.sup.3L=OCHF.sub.2, R.sup.11L=H, R.sup.12L=H], [5018; Q=Q.sup.p1, R.sup.1L=H, R.sup.2L=OCF.sub.3, R.sup.3L=H, R.sup.11L=H, R.sup.12L=H], [5019; Q=Q.sup.p1, R.sup.1L=H, R.sup.2L=H, R.sup.3L=OCF.sub.3, R.sup.11L=H, R.sup.12L=H], [5020; Q=Q.sup.p1, R.sup.11L=H, R.sup.2L=SMe, R.sup.3L=H, R.sup.11L=H, R.sup.12L=H], [5021; Q=Q.sup.p1, R.sup.1L=H, R.sup.2L=H, R.sup.3L=SMe, R.sup.11L=H, R.sup.12L=H], [5022; Q=Q.sup.p1, R.sup.1L=H, R.sup.2L=SCF.sub.3, R.sup.3L=H, R.sup.11L=H, R.sup.12L=H], [5023; Q=Q.sup.p1, R.sup.1L=H, R.sup.2L=H, R.sup.3L=SCF.sub.3, R.sup.11L=H, R.sup.12L=H], [5024; Q=Q.sup.p1, R.sup.1L=H, R.sup.2L=N, R.sup.3L=H, R.sup.11L=H, R.sup.12L=H], [5025; Q=Q.sup.p1, R.sup.1L=H, R.sup.2L=H, R.sup.3L=N, R.sup.11L=H, R.sup.12L=H], [5026; Q=Q.sup.p1, R.sup.1L=H, R.sup.2L=H, R.sup.3L=H, R.sup.11L=H, R.sup.12L=H], [5027; Q=Q.sup.p1, R.sup.1L=H, R.sup.2L=H, R.sup.3L=NO.sub.2, R.sup.11L=H, R.sup.12L=H], [5028; Q=Q.sup.p1, R.sup.1L=H, R.sup.2L=Cl, R.sup.3L=H, R.sup.11L=Cl, R.sup.12L=H], [5029; Q=Q.sup.p1, R.sup.1L=H, R.sup.2L=Me, R.sup.3L=H, R.sup.11L=Me, R.sup.12L=H], [5030; Q=Q.sup.p2, R.sup.3L=H, R.sup.11L=H, R.sup.12L=H], [5031; Q=Q.sup.p2, R.sup.3L=F, R.sup.11L=H, R.sup.12L=H], [5032; Q=Q.sup.p2, R.sup.3L=H, R.sup.11L=F, R.sup.12L=H], [5033; Q=Q.sup.p2, R.sup.3L=H, R.sup.11L=H, R.sup.12L=F], [5034; Q.sup.p2, R.sup.3L=Cl, R.sup.11L=H, R.sup.12L=H], [5035; Q=Q.sup.p2, R.sup.3L=H, R.sup.11L=Cl, R.sup.12L=H], [5036; Q=Q.sup.p2, R.sup.3L=H, R.sup.11L=H, R.sup.12L=H], [5037; Q=Q.sup.p2, R.sup.3L=H, R.sup.11L=OMe, R.sup.12L=H], [5038; Q=Q.sup.p2, R.sup.3L=CF.sub.3, R.sup.11L=H, R.sup.12L=H], [5039; Q=Q.sup.p2, R.sup.3L=H, R.sup.11L=CF.sub.3, R.sup.12L=H], [5040; Q=Q.sup.p3, R.sup.3L=H, R.sup.11L=H, R.sup.12L=H], [5041; Q=Q.sup.p3, R.sup.3L=F, R.sup.11L=H, R.sup.12L=H], [5042; Q=Q.sup.p3, R.sup.3L=H, R.sup.11=F, R.sup.12L=H], [5043; Q=Q.sup.p3, R.sup.3L=H, R.sup.11L=H, R.sup.12L=F], [5044; Q=Q.sup.p3, R.sup.3L=Cl, R.sup.11L=H, R.sup.12L=H], [5045; Q=Q.sup.p3, R.sup.3L=H, R.sup.11L=Cl, R.sup.12L=H], [5046; Q=Q.sup.p3, R.sup.3L=OMe, R.sup.11L=H, R.sup.12L=H], [5047; Q=Q.sup.p3, R.sup.3L=H, R.sup.11L=OMe, R.sup.12L=H], [5048; Q=Q.sup.p3, R.sup.3L=CF.sub.3, R.sup.11L=H, R.sup.12L=H], [5049; Q=Q.sup.p3, R.sup.3L=H, R.sup.11L=CF.sub.3, R.sup.12L=H], [5050; Q=Q.sup.p3, R.sup.3L=H, R.sup.11L=H, R.sup.12L=H], [5051; Q=Q.sup.p4, R.sup.3=F, R.sup.11L=H, R.sup.12L=H], [5052; Q=Q.sup.p4, R.sup.3L=H, R.sup.11L=F, R.sup.12L=H], [5053; Q=Q.sup.p4, R.sup.3L=H, R.sup.11L=H, R.sup.12L=F], [5054; Q=Q.sup.p4, R.sup.3L=Cl, R.sup.11L=H, R.sup.12L=H], [5055; Q=Q.sup.p4, R.sup.3L=H, R.sup.11L=Cl, R.sup.12L=H], [5056; Q=Q.sup.p4, R.sup.3L=OMe, R.sup.11L=H, R.sup.12L=H], [5057; Q=Q.sup.p4, R.sup.3L=H, R.sup.11L=OMe, R.sup.12L=H], [5058; Q=Q.sup.p4, R.sup.3L=CF.sub.3, R.sup.11L=H, R.sup.12L=H], [5059; Q=Q.sup.p4, R.sup.3L=H, R.sup.11L=CF.sub.3, R.sup.12L=H], [5060; Q=Q.sup.p5, R.sup.3L=H, R.sup.11L=H, R.sup.12L=H], [5061; Q=Q.sup.p5, R.sup.3L=F, R.sup.11L=H, R.sup.12L=H], [5062; Q=Q.sup.p5, R.sup.3L=H, R.sup.11L=F, R.sup.12L=H], [5063; Q=Q.sup.p5, R.sup.3L=H, R.sup.11L=H, R.sup.12L=F], [5064; Q=Q.sup.p5, R.sup.3L=Cl, R.sup.11L=H, R.sup.12L=H], [5065; Q=Q.sup.p5, R.sup.3L=H, R.sup.11L=Cl, R.sup.12L=H], [5066; Q=Q.sup.p5, R.sup.3L=OMe, R.sup.11L=H, R.sup.12L=H], [5067; Q=Q.sup.p5, R.sup.3L=H, R.sup.11L=OMe, R.sup.12L=H], [5068; Q=Q.sup.p5, R.sup.3L=CF.sub.3, R.sup.11L=H, R.sup.12L=H], [5069; Q=Q.sup.p5, R.sup.3L=H, R.sup.11L=CF.sub.3, R.sup.12L=H], [5070; Q=Q.sup.p5, R.sup.1L=H, R.sup.11L=H, R.sup.12L=H], [5071; Q=Q.sup.p6, R.sup.1L=F, R.sup.1L=H, R.sup.12L=H], [5072; Q=Q.sup.p6, R.sup.1L=H, R.sup.11L=F, R.sup.12L=H], [5073; Q=Q.sup.p6, R.sup.1L=H, R.sup.11L=H, R.sup.12L=F], [5074; Q=Q.sup.p6, R.sup.1L=H, R.sup.11L=Cl, R.sup.12L=H], [5075; Q=Q.sup.p6, R.sup.1L=H, R.sup.11L=OMe, R.sup.12L=H], [5076; Q=Q.sup.p6, R.sup.1L=H, R.sup.11L=CF.sub.3, R.sup.12L=H], [5077; Q=Q.sup.p7, R.sup.1L=H, R.sup.11L=H, R.sup.12L=H], [5078; Q=Q.sup.p7, R.sup.1L=F, R.sup.11L=H, R.sup.12L=H], [5079; Q=Q.sup.p7, R.sup.1L=H, R.sup.11L=F, R.sup.12L=H], [5080; Q=Q.sup.p7, R.sup.1L=H, R.sup.11L=H, R.sup.12L=F], [5081; Q=Q.sup.p7, R.sup.1L=H, R.sup.11L=Cl, R.sup.12L=H], [5082; Q=Q.sup.p7, R.sup.1L=H, R.sup.11L=OMe, R.sup.12L=H], [5083; Q=Q.sup.p7, R.sup.1L=H, R.sup.11L=CF.sub.3, R.sup.12L=H], [5084; Q=Q.sup.p8, R.sup.1L=H, R.sup.11L=H, R.sup.12L=H], [5085; Q=Q.sup.p8, R.sup.1L=F, R.sup.11L=H, R.sup.12L=H], [5086; Q=Q.sup.p8, R.sup.1L=H, R.sup.11L=F, R.sup.12L=H], [5087; Q=Q.sup.p8, R.sup.1L=H, R.sup.11L=H, R.sup.12L=F], [5088; Q=Q.sup.p8, R.sup.1L=H, R.sup.11L=Cl, R.sup.12L=H], [5089; Q=Q.sup.p8, R.sup.1L=H, R.sup.11L=OMe, R.sup.12L=H], [5090; Q=Q.sup.p8, R.sup.1L=H, R.sup.11L=CF.sub.3, R.sup.12L=H], [5091; Q=Q.sup.p9, R.sup.3L=H, R.sup.11L=H, R.sup.12L=H], [5092; Q=Q.sup.p9, R.sup.3L=F, R.sup.11L=H, R.sup.12L=H], [5093; Q=Q.sup.p9, R.sup.3L=H, R.sup.1L=F, R.sup.12L=H], [5094; Q=Q.sup.p9, R.sup.3L=H, R.sup.11L=H, R.sup.12L=F], [5095; Q=Q.sup.p9, R.sup.3L=Cl, R.sup.11L=H, R.sup.12L=H], [5096; Q=Q.sup.p9, R.sup.3L=H, R.sup.11L=Cl, R.sup.12L=H], [5097; Q=Q.sup.p9, R.sup.3L=OMe, R.sup.11L=H, R.sup.12L=H], [5098; Q=Q.sup.p9, R.sup.3L=H, R.sup.11L=OMe, R.sup.12L=H], [5099; Q=Q.sup.p9, R.sup.3L=CF.sub.3, R.sup.11L=H, R.sup.12L=H], [5100; Q=Q.sup.p9, R.sup.3L=H, R.sup.11L=CF.sub.3, R.sup.12L=H], [5101; Q=Q.sup.p10, R.sup.1L=H, R.sup.11L=H, R.sup.12L=H], [5102; Q=Q.sup.p10, R.sup.1L=F, R.sup.11L=H, R.sup.12L=H], [5103; Q=Q.sup.p10, R.sup.1L=H, R.sup.11L=F, R.sup.12L=H], [5104; Q=Q.sup.p10, R.sup.1L=H, R.sup.11L=H, R.sup.12L=F], [5105; Q=Q.sup.p10, R.sup.1L=H, R.sup.11L=Cl, R.sup.12L=H], [5106; Q=Q.sup.p10, R.sup.1L=H, R.sup.11L=OMe, R.sup.12L=H], and [5107; Q=Q.sup.p10, R.sup.1L=H, R.sup.11L=CF.sub.3, R.sup.12L=H]

(1279) Formulation Examples will be shown below. Parts are by weight.

Formulation Example 1

(1280) Fifty parts (50 parts) of any one of the present compounds 1 to 159, 201 to 219, and 251 to 266, 3 parts of calcium ligninsulfoate, 2 parts of laurylmagnesium sulfate, and 45 parts of synthetic hydrated silicon oxide are thoroughly ground and mixed to obtain each formulation.

Formulation Example 2

(1281) Twenty parts (20 parts) of any one of the present compounds 1 to 159, 201 to 219, and 251 to 266, and 1.5 parts of sorbitan trioleate were mixed with 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol and the mixture was finely ground by a wet grinding method. Then, 40 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added thereto and 10 parts of propylene glycol is further added, followed by stirring and mixing to obtain each formulation.

Formulation Example 3

(1282) Two parts (2 parts) of any one of the present compounds 1 to 159, 201 to 219, and 251 to 266, 88 parts of kaolin clay, and 10 parts of talc are thoroughly ground and mixed to obtain each formulation.

Formulation Example 4

(1283) Five parts (5 parts) of any one of the present compounds 1 to 159, 201 to 219, and 251 to 266, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate, and 75 parts of xylene are thoroughly ground and mixed to obtain each formulation.

Formulation Example 5

(1284) Two parts (2 parts) of any one of the present compounds 1 to 159, 201 to 219, and 251 to 266, 1 part of synthetic hydrated silicon oxide, 2 parts of calcium ligninsulfoate, 30 parts of bentonite, and 65 parts of kaolin clay are thoroughly ground and mixed. After the addition of water, the mixture is thoroughly kneaded and further and granulated and dried to obtain each formulation.

Formulation Example 6

(1285) Ten parts (10 parts) of any one of the present compounds 1 to 159, 201 to 219, and 251 to 266, 35 parts of white carbon containing 50 parts of a polyoxyethylene alkyl ether sulfate ammonium salt, and 55 parts of water were finely ground by a wet grinding method to obtain each formulation.

(1286) The following Test Examples will show that the present compounds are useful for controlling pests.

(1287) The control effect was evaluated by visually observing the area of lesion spots on each of test plants at the time of investigation, and comparing the area of lesion spots on a plant treated with the present control compound with that on an untreated plant.

Test Example 1

(1288) Each of plastic pots was filled with soil and rice (cultivar: NIHONBARE) was sowed therein and grown in a greenhouse for 20 days. Each of the present compounds 5, 7, 24, 30, 31, 32, 34, 37, 44, 69, 71, 76, 85, 96, 97, 110, 124, 127, 129, 133, 136, 137, 139, 142, 143, 144, 149, 152, 153, 154, 202, 203, 204, 211, 215, 217, and 265 was formulated into a formulation according to Formulation Example, which was diluted with water to adjust to a prescribed concentration of 500 ppm. The obtained diluted solutions were sprayed over stems and leaves so that they sufficiently adhered to the surface of the leaves of the rice. After spraying, the plant was air-dried and subjected to a spraying treatment and the rice seedling (cultivar: NIHONBARE) infected by the rice blast fungus (Magnaporthe grisea) were left to stand for 6 days at 24° C. in the daytime and 20° C. at night under high humidity condition, while being in contact with each other, and then the area of lesion spots was investigated. As a result, the lesion areas on all of the plant treated with the present compounds 5, 7, 24, 30, 31, 32, 34, 37, 44, 69, 71, 76, 85, 96, 97, 110, 124, 127, 129, 133, 136, 137, 139, 142, 143, 144, 149, 152, 153, 154, 265, 202, 203, 204, 211, 215, 217, and 265 showed 30% or less with respect to the lesion area on the non-treated plant.

Test Example 2

(1289) Each of plastic pots was filled with soil and wheat (cultivar: SHIROGANE) was sowed therein and grown in a greenhouse for 9 days. Each of the present compounds 24, 30, 31, 34, 38, 44, 101, 110, 119, 137, 138, 152, 153, 154, 202, 203, 204, 215, and 217 was formulated into a formulation according to Formulation Example, which was diluted with water to adjust to a prescribed concentration of 500 ppm. The obtained diluted solution was sprayed over stems and leaves of the wheat so that they sufficiently adhered to the surface of the leaves of the wheat. After spraying, the plant was air-dried and cultivated at 20° C. for 5 days under illumination, and then inoculated by sprinkling with spores of the wheat rust fungus (Puccinia recondita). After the inoculation, the plant was left to stand at 23° C. for one day under dark and high humidity condition, and cultivated under illumination at 20° C. for 8 days, and then the area of lesion spots was investigated. As a result, it has been found that the area of lesion spots on all of the plant treated with each of the present compounds 24, 30, 31, 34, 38, 44, 101, 110, 119, 137, 138, 152, 153, 154, 202, 203, 204, 215, and 217 showed 30% or less of that on an untreated plant.

Test Example 3

(1290) Each of plastic pots was filled with soil and barley (cultivar: MIKAMO GOLDEN) was sowed therein and grown in a greenhouse for 7 days. Each of the present compounds 1, 2, 5, 7, 9, 11, 12, 15, 16, 17, 19, 23, 24, 25, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 53, 54, 55, 56, 57, 58, 59, 60, 61, 64, 65, 66, 67, 68, 69, 70, 71, 72, 75, 76, 78, 79, 80, 82, 84, 85, 86, 87, 88, 89, 92, 93, 95, 96, 97, 99, 101, 105, 106, 107, 109, 110, 112, 113, 114, 115, 116, 118, 119, 120, 122, 123, 124, 125, 127, 129, 131, 132, 133, 134, 135, 136, 137, 138, 139, 141, 142, 143, 144, 145, 146, 148, 149, 151, 152, 153, 154, 155, 156, 159, 202, 203, 204, 205, 206, 207, 209, 210, 213, 215, 216, 217, 257, 258, 259, 260, 261, 262, 263, 264, and 265 was formulated into a formulation according to Formulation Example, which was diluted with water to adjust to a prescribed concentration of 500 ppm. The obtained diluted solution was sprayed over stems and leaves of the barley so that they sufficiently adhered to the surface of the leaves of the barley. After spraying, the plant was air-dried. Two days later, an aqueous suspension containing conidiospores of barley net blotch fungus (Pyrenophora teres) was sprayed to inoculate the spores. After completion of the inoculation, the plant was left to stand for 3 days in a greenhouse at 23° C. in the daytime and 20° C. at night under high humidity condition and cultivated in a greenhouse for 7 days, and then the area of lesion spots was investigated. As a result, it has been found that the area of lesion spots on all of the plant treated with each of the present compounds 1, 2, 5, 7, 9, 11, 12, 15, 16, 17, 19, 23, 24, 25, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 53, 54, 55, 56, 57, 58, 59, 60, 61, 64, 65, 66, 67, 68, 69, 70, 71, 72, 75, 76, 78, 79, 80, 82, 84, 85, 86, 87, 88, 89, 92, 93, 95, 96, 97, 99, 101, 105, 106, 107, 109, 110, 112, 113, 114, 115, 116, 118, 119, 120, 122, 123, 124, 125, 127, 129, 131, 132, 133, 134, 135, 136, 137, 138, 139, 141, 142, 143, 144, 145, 146, 148, 149, 151, 152, 153, 154, 155, 156, 159, 202, 203, 204, 205, 206, 207, 209, 210, 213, 215, 216, 217, 257, 258, 259, 260, 261, 262, 263, 264, and 265 showed 30% or less of that on an untreated plant.

Test Example 4

(1291) Each of plastic pots was filled with soil and kidney bean (cultivar: NAGAUZURA INGEN) was sowed therein and grown in a greenhouse for 8 days. Each of the present compounds 1, 2, 5, 7, 8, 9, 10, 11, 12, 16, 17, 19, 24, 27, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 42, 44, 46, 47, 48, 49, 50, 53, 54, 55, 56, 58, 61, 65, 67, 68, 69, 70, 71, 76, 78, 79, 84, 85, 86, 89, 90, 92, 93, 95, 96, 97, 101, 105, 107, 108, 109, 110, 118, 119, 122, 123, 124, 125, 127, 128, 129, 130, 131, 132, 133, 135, 136, 137, 138, 139, 142, 143, 144, 145, 146, 149, 151, 152, 153, 202, 203, 204, 205, 206, 208, 214, 215, 216, 217, 257, 258, and 259 was formulated into a formulation according to Formulation Example, which was diluted with water to adjust to a prescribed concentration of 500 ppm. The obtained diluted solution was sprayed over stems and leaves of the kidney bean so that they sufficiently adhered to the surface of the leaves of the kidney bean. After spraying, the plant was air-dried and a PDA medium containing hyphae of the kidney bean stem rot fungus (Sclerotinia sclerotiorum) was placed on the leaves of the kidney bean. After the inoculation, all kidney beans are left to stand under high humidity condition only at night. Four days after the inoculation, the area of lesion spots was investigated. As a result, the area of lesion spots on all of the plant treated with each of the present compounds 1, 2, 5, 7, 8, 9, 10, 11, 12, 16, 17, 19, 24, 27, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 42, 44, 46, 47, 48, 49, 50, 53, 54, 55, 56, 58, 61, 65, 67, 68, 69, 70, 71, 76, 78, 79, 84, 85, 86, 89, 90, 92, 93, 95, 96, 97, 101, 105, 107, 108, 109, 110, 118, 119, 122, 123, 124, 125, 127, 128, 129, 130, 131, 132, 133, 135, 136, 137, 138, 139, 142, 143, 144, 145, 146, 149, 151, 152, 153, 202, 203, 204, 205, 206, 208, 214, 215, 216, 217, 257, 258, and 259 showed 30% or less of that on an untreated plant.

Test Example 5

(1292) Each of plastic pots was filled with soil and wheat (cultivar: APOGEE) was sowed therein and grown in a greenhouse for 10 days. Each of the present compounds 1, 5, 7, 9, 10, 11, 12, 15, 16, 17, 19, 23, 24, 25, 29, 30, 31, 32, 34, 35, 36, 37, 38, 39, 41, 42, 44, 45, 46, 47, 48, 49, 50, 51, 53, 54, 55, 56, 57, 58, 59, 60, 61, 64, 65, 67, 68, 69, 70, 71, 72, 75, 77, 78, 79, 84, 85, 86, 88, 89, 90, 91, 92, 93, 95, 96, 97, 99, 100, 101, 102, 105, 106, 107, 108, 109, 110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 120, 122, 123, 124, 125, 126, 127, 128, 129, 130, 131, 132, 133, 134, 135, 136, 137, 138, 139, 140, 141, 142, 143, 144, 145, 146, 148, 149, 151, 152, 153, 154, 155, 156, 202, 203, 204, 207, 211, 215, 216, 217, 257, 258, 259, 261, 262, 264, and 265 was formulated into a formulation according to Formulation Example, which was diluted with water to adjust to a prescribed concentration of 500 ppm. The obtained diluted solution was sprayed over stems and leaves of the wheat so that they sufficiently adhered to the surface of the leaves of the wheat. After spraying, the plant was air-dried. Four days later, an aqueous suspension containing conidiospores of the wheat leaf blotch fungus (Septoria tritici) was sprayed to inoculate the spores. After completion of the inoculation, the plant was left to stand at 18° C. under high humidity condition for 3 days and left to stand under illumination for 14 to 18 days, and then the area of lesion spots was investigated. As a result, the area of lesion spots on all of the plant treated with each of the present compounds 1, 5, 7, 9, 10, 11, 12, 15, 16, 17, 19, 23, 24, 25, 29, 30, 31, 32, 34, 35, 36, 37, 38, 39, 41, 42, 44, 45, 46, 47, 48, 49, 50, 51, 53, 54, 55, 56, 57, 58, 59, 60, 61, 64, 65, 67, 68, 69, 70, 71, 72, 75, 77, 78, 79, 84, 85, 86, 88, 89, 90, 91, 92, 93, 95, 96, 97, 99, 100, 101, 102, 105, 106, 107, 108, 109, 110, 111, 112, 113, 114, 115, 116, 117, 118, 119, 120, 122, 123, 124, 125, 126, 127, 128, 129, 130, 131, 132, 133, 134, 135, 136, 137, 138, 139, 140, 141, 142, 143, 144, 145, 146, 148, 149, 151, 152, 153, 154, 155, 156, 202, 203, 204, 207, 211, 215, 216, 217, 257, 258, 259, 261, 262, 264, and 265 showed 30% or less of that on an untreated plant.

Test Example 6

(1293) Each of plastic pots was filled with soil and cucumber (cultivar: SAGAMI HANJIRO) was sowed therein and grown in a greenhouse for 12 days. Each of the present compounds 1, 2, 5, 7, 9, 10, 11, 12, 15, 16, 17, 19, 23, 24, 25, 27, 29, 30, 31, 32, 33, 34, 35, 38, 39, 40, 44, 45, 46, 48, 49, 51, 53, 54, 55, 56, 58, 59, 60, 61, 62, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 76, 77, 78, 79, 83, 84, 85, 86, 88, 89, 90, 91, 92, 93, 95, 96, 99, 100, 101, 102, 105, 106, 107, 108, 109, 110, 111, 112, 113, 114, 115, 116, 118, 119, 120, 123, 124, 125, 126, 127, 128, 129, 131, 132, 133, 134, 135, 136, 137, 138, 139, 142, 143, 144, 145, 148, 149, 151, 153, 154, 155, 156, 202, 203, 204, 205, 208, 211, 212, 213, 214, 215, 216, 217, 257, 258, 260, 261, 262, and 263 was formulated into a formulation according to Formulation Example, which was diluted with water to adjust to a prescribed concentration of 500 ppm. The obtained diluted solution was sprayed over stems and leaves of the cucumber so that they sufficiently adhered to the surface of the leaves of the cucumber. After spraying, the plant was air-dried and then inoculated by sprinkling with spores of the cucumber powdery mildew fungus (Sphaerotheca fuliginea). After the inoculation, the plant was cultivated in a greenhouse at 24° C. in the daytime and 20° C. at night for 8 days, and then the area of lesion spots was investigated. As a result, the area of lesion spots on all of the plant treated with each of the present compounds 1, 2, 5, 7, 9, 10, 11, 12, 15, 16, 17, 19, 23, 24, 25, 27, 29, 30, 31, 32, 33, 34, 35, 38, 39, 40, 44, 45, 46, 48, 49, 51, 53, 54, 55, 56, 58, 59, 60, 61, 62, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 76, 77, 78, 79, 83, 84, 85, 86, 88, 89, 90, 91, 92, 93, 95, 96, 99, 100, 101, 102, 105, 106, 107, 108, 109, 110, 111, 112, 113, 114, 115, 116, 118, 119, 120, 123, 124, 125, 126, 127, 128, 129, 131, 132, 133, 134, 135, 136, 137, 138, 139, 142, 143, 144, 145, 148, 149, 151, 153, 154, 155, 156, 202, 203, 204, 205, 208, 211, 212, 213, 214, 215, 216, 217, 257, 258, 260, 261, 262, and 263 showed 30% or less of that on an untreated plant.

Test Example 7

(1294) Each of plastic pots was filled with soil and rice (cultivar: NIHONBARE) was sowed therein and grown in a greenhouse for 20 days. Each of the present compounds 2, 3, 6, 9, 10, 13, 16, 17, 19, 23, 47, 48, 53, 54, 55, 56, 57, 58, 60, 65, 70, 72, 73, 84, 94, 95, 101, 107, 112, 118, 119, 126, 131, 132, 134, 135, 138, 148, 150, 151, 155, 201, 214, 216, 258, and 260 was formulated into a formulation according to Formulation Example, which was diluted with water to adjust to a prescribed concentration of 200 ppm. The obtained diluted solutions were sprayed over stems and leaves so that they sufficiently adhered to the surface of the leaves of the rice. After spraying, the plant was air-dried and subjected to a spraying treatment and the rice seedling (cultivar: NIHONBARE) infected by the rice blast fungus (Magnaporthe grisea) were left to stand for 6 days at 24° C. in the daytime and 20° C. at night under high humidity condition, while being in contact with each other, and then the area of lesion spots was investigated. As a result, the lesion areas on all of the plant treated with the present compounds 2, 3, 6, 9, 10, 13, 16, 17, 19, 23, 47, 48, 53, 54, 55, 56, 57, 58, 60, 65, 70, 72, 73, 84, 94, 95, 101, 107, 112, 118, 119, 126, 131, 132, 134, 135, 138, 148, 150, 151, 155, 201, 214, 216, 258, and 260 showed 30% or less with respect to the lesion area on the non-treated plant.

Test Example 8

(1295) Each of plastic pots was filled with soil and wheat (cultivar: SHIROGANE) was sowed therein and grown in a greenhouse for 9 days. Each of the present compounds 7, 10, 39, 54, 56, 61, 75, 78, 86, 88, 90, 92, 94, 99, 100, 105, 106, 107, 118, 120, 124, 125, 127, 132, 134, 136, 142, 143, 144, 148, 149, 206, 213, 216, and 258 was formulated into a formulation according to Formulation Example, which was diluted with water to adjust to a prescribed concentration of 200 ppm. The obtained diluted solution was sprayed over stems and leaves of the wheat so that they sufficiently adhered to the surface of the leaves of the wheat. After spraying, the plant was air-dried and cultivated at 20° C. for 5 days under illumination, and then inoculated by sprinkling with spores of the wheat rust fungus (Puccinia recondita). After the inoculation, the plant was left to stand at 23° C. for one day under dark and high humidity condition, and cultivated under illumination at 20° C. for 8 days, and then the area of lesion spots was investigated. As a result, it has been found that the area of lesion spots on all of the plant treated with each of the present compounds 7, 10, 39, 54, 56, 61, 75, 78, 86, 88, 90, 92, 92, 99, 94, 99, 100, 105, 106, 107, 118, 120, 124, 125, 127, 132, 134, 136, 142, 143, 144, 148, 149, 206, 213, 216, and 258 showed 30% or less of that on an untreated plant.

Test Example 9

(1296) Each of plastic pots was filled with soil and barley (cultivar: MIKAMO GOLDEN) was sowed therein and grown in a greenhouse for 7 days. Each of the present compounds 3, 10, 27, 62, 90, 94, 108, 121, 126, 128, 130, 147, 151, 201, and 205 was formulated into a formulation according to Formulation Example, which was diluted with water to adjust to a prescribed concentration of 200 ppm. The obtained diluted solution was sprayed over stems and leaves of the barley so that they sufficiently adhered to the surface of the leaves of the barley. After spraying, the plant was air-dried. Two days later, an aqueous suspension containing conidiospores of barley net blotch fungus (Pyrenophora teres) was sprayed to inoculate the spores. After completion of the inoculation, the plant was left to stand for 3 days in a greenhouse at 23° C. in the daytime and 20° C. at night under high humidity condition and cultivated in a greenhouse for 7 days, and then the area of lesion spots was investigated. As a result, the area of lesion spots on all of the plant treated with each of the present compounds 3, 10, 27, 62, 90, 94, 108, 121, 126, 128, 130, 147, 151, 201, and 205 showed 30% or less of that on an untreated plant.

Test Example 10

(1297) Each of plastic pots was filled with soil and kidney bean (cultivar: NAGAUZURA INGEN) was sowed therein and grown in a greenhouse for 8 days. Each of the present compounds 63, 66, 72, 87, 88, 91, 116, 117, 155, and 201 was formulated into a formulation according to Formulation Example, which was diluted with water to adjust to a prescribed concentration of 200 ppm. The obtained diluted solution was sprayed over stems and leaves of the kidney bean so that they sufficiently adhered to the surface of the leaves of the kidney bean. After spraying, the plant was air-dried and a PDA medium containing hyphae of the kidney bean stem rot fungus (Sclerotinia sclerotiorum) was placed on the leaves of the kidney bean. After the inoculation, all kidney beans are left to stand under high humidity condition only at night. Four days after the inoculation, the area of lesion spots was investigated. As a result, the area of lesion spots on all of the plant treated with any one of the present compounds 63, 66, 72, 87, 88, 91, 116, 117, 155, and 201 showed 30% or less of that on an untreated plant.

Test Example 11

(1298) Each of plastic pots was filled with soil and wheat (cultivar: APOGEE) was sowed therein and grown in a greenhouse for 10 days. Each of the present compounds 2, 3, 27, 28, 43, 62, 63, 66, 76, 94, 121, 147, 159, 205, and 260 was formulated into a formulation according to Formulation Example, which was diluted with water to adjust to a prescribed concentration of 200 ppm. The obtained diluted solution was sprayed over stems and leaves of the wheat so that they sufficiently adhered to the surface of the leaves of the wheat. After spraying, the plant was air-dried. Four days later, an aqueous suspension containing conidiospores of the wheat leaf blotch fungus (Septoria tritici) was sprayed to inoculate the spores. After completion of the inoculation, the plant was left to stand at 18° C. under high humidity condition for 3 days and left to stand under illumination for 14 to 18 days, and then the area of lesion spots was investigated. As a result, the area of lesion spots on all of the plant treated with each of the present compounds 2, 3, 27, 28, 43, 62, 63, 65, 66, 76, 94, 121, 147, 159, 205, and 260 showed 30% or less of that on an untreated plant.

Test Example 12

(1299) Each of plastic pots was filled with soil and cucumber (cultivar: SAGAMI HANJIRO) was sowed therein and grown in a greenhouse for 12 days. Each of the present compounds 42, 57, 94, 121, and 152 was formulated into a formulation according to Formulation Example, which was diluted with water to adjust to a prescribed concentration of 200 ppm. The obtained diluted solution was sprayed over stems and leaves of the cucumber so that they sufficiently adhered to the surface of the leaves of the cucumber. After spraying, the plant was air-dried and then inoculated by sprinkling with spores of the cucumber powdery mildew fungus (Sphaerotheca fuliginea). After the inoculation, the plant was cultivated in a greenhouse at 24° C. in the daytime and 20° C. at night for 8 days, and then the area of lesion spots was investigated. As a result, the area of lesion spots on all of the plant treated with each of the present compounds 42, 57, 94, 121, and 152 showed 30% or less of that on an untreated plant.

Test Example 13

(1300) Each of plastic pots was filled with soil and soybean (cultivar: KUROSENGOKU) was sowed therein and grown in a greenhouse for 13 days. Each of the present compounds 38, 110, 144, 152, 203, 215, and 217 was formulated into a formulation according to Formulation Example, which was diluted with water to adjust to a prescribed concentration of 200 ppm. The obtained diluted solution was sprayed over stems and leaves of the soybean so that they sufficiently adhered to the surface of the leaves of the soybean. After spraying, the plant was air-dried. Two days later, an aqueous suspension containing conidiospores of soybean rust fungus (Phakopsora pachyrhizi) was sprayed to inoculate the spores. After completion of the inoculation, the plant was left to stand for 3 days in a greenhouse at 23° C. in the daytime and 20° C. at night under high humidity condition and cultivated in a greenhouse for 14 days, and then the area of lesion spots was investigated. As a result, it has been found that the area of lesion spots on all of the plant treated with each of the present compounds 38, 110, 144, 152, 203, 215, and 217 showed 30% or less of that on an untreated plant.

Test Example 14

(1301) Each of plastic pots was filled with soil and barley (cultivar: MIKAMO GOLDEN) was sowed therein and grown in a greenhouse for 7 days. Each of the present compounds 1, 2, 5, 7, 8, 9, 10, 11, 12, 16, 17, 19, 23, 25, 27, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 46, 47, 48, 49, 51, 53, 54, 55, 56, 58, 59, 60, 61, 64, 65, 66, 68, 69, 70, 71, 72, 73, 75, 76, 77, 78, 79, 84, 85, 88, 92, 93, 94, 95, 96, 97, 98, 99, 103, 105, 106, 107, 108, 109, 110, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 122, 123, 124, 125, 126, 127, 128, 129, 130, 131, 132, 133, 134, 136, 137, 138, 139, 140, 141, 142, 143, 144, 145, 146, 147, 148, 149, 151, 152, 155, 201, 202, 203, 205, 206, 207, 209, 211, 213, 214, 215, 216, 217, 219, 257, 258, 259, 260, and 262 was formulated into a formulation according to Formulation Example, which was diluted with water to adjust to a prescribed concentration of 200 ppm. The obtained diluted solution was sprayed over stems and leaves of the barley so that they sufficiently adhered to the surface of the leaves of the barley. After spraying, the plant was air-dried. Two days later, an aqueous suspension containing conidiospores of barley scald fungus (Rhynchosporium secalis) was sprayed to inoculate the spores. After completion of the inoculation, the plant was left to stand for 3 days in a greenhouse at 23° C. in the daytime and 20° C. at night under high humidity condition and cultivated in a greenhouse for 7 days, and then the area of lesion spots was investigated. As a result, it has been found that the area of lesion spots on all of the plant treated with each of the present compounds 1, 2, 5, 7, 8, 9, 10, 11, 12, 16, 17, 19, 23, 25, 27, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 46, 47, 48, 49, 51, 53, 54, 55, 56, 58, 59, 60, 61, 64, 65, 66, 68, 69, 70, 71, 72, 73, 75, 76, 77, 78, 79, 84, 85, 88, 92, 93, 94, 95, 96.97, 98, 99, 103, 105, 106, 107, 108, 109, 110, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 122, 123, 124, 125, 126, 127, 128, 129, 130, 131, 132, 133, 134, 136, 137, 138, 139, 140, 141, 142, 143, 144, 145, 146, 147, 148, 149, 151, 152, 155, 201, 202, 203, 205, 206, 207, 209, 211, 213, 214, 215, 216, 217, 219, 257, 258, 259, 260, and 262 showed 30% or less of that on an untreated plant.

Test Example 15

(1302) Each of formulations of the present compounds 6, 9, 26, 28, 31, 32, 33, 36, 71, 109, 114, 115, 125, and 149 obtained in Formulation Example 6 was diluted with water so that the concentration of the active ingredient is controlled to 500 ppm to prepare a test spraying solution. Meanwhile, the above test chemical solution was sprayed over three-leaf stage cabbage sowed in a polyethylene cup in the proportion of 20 mL/cup. After drying the chemical solution, stem and leaf portions were cut off and put in a 50 mL cup and five second-instar larvae of diamondback moth (Plutella xylostella) were released, and then the cup was capped. The cup was stored at 25° C. and, after 5 days, the number of surviving worms was counted and mortality was determined by the following equation.
Mortality (%)=[(Number of dead insects)/(Number of tested insects)]×100

(1303) As a result, the treated area of the test spraying solutions of the present compounds 6, 9, 26, 28, 31, 32, 33, 36, 71, 109, 114, 115, 125, and 149 exhibited mortality of 80% or more.

Comparative Test Example

(1304) Each of plastic pots was filled with soil and cucumber (cultivar: SAGAMI HANJIRO) was sowed therein and grown in a greenhouse for 12 days.

(1305) Each of 1-methyl-4-{2-methyl-6-[1-(3-trifluoromethylphenyl)ethylideneaminooxymethyl]phenyl}-1,4-dihydrotetrazol-5-one and 1-{3-methyl-2-[1-(3-trifluoromethylphenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one was formulated into a formulation according to Formulation Example, which was diluted with water to adjust to a prescribed concentration of 200 ppm. The obtained diluted solution was sprayed over stems and leaves of the cucumber so that they sufficiently adhered to the surface of the leaves of the cucumber. After spraying, the plant was air-dried and then inoculated by sprinkling with spores of the cucumber powdery mildew fungus (Sphaerotheca fuliginea). After the inoculation, the plant was cultivated in a greenhouse at 24° C. in the daytime and 20° C. at night for 8 days, and then the area of lesion spots was investigated. As a result, the area of lesion spots on the plant treated with 1-methyl-4-{2-methyl-6-[1-(3-trifluoromethylphenyl)ethylideneaminooxymethyl]phenyl}-1,4-dihydrotetrazol-5-one was 70% or more of that on an untreated plant, whereas, the area of lesion spots on the plant treated with 1-{3-methyl-2-[1-(3-trifluoromethylphenyl)ethylideneaminooxymethyl]phenyl}-4-methyl-1,4-dihydrotetrazol-5-one was 30% or less of that on an untreated plant.