Alkyl phenyl sulfide derivative and pest control agent

Abstract

An alkyl phenyl sulfide derivative represented by the general formula [I] or an agriculturally acceptable salt thereof, and a pest control agent containing the derivative or the salt as an active ingredient. ##STR00001##
[in the above formula, R.sup.1 is, for example, a C.sub.1C.sub.6 alkyl group which is mono- or poly-substituted with halogen atom; R.sup.2 is, for example, a halogen atom or a C.sub.1C.sub.6 alkyl group; R.sup.3 is, for example, a hydrogen atom or a halogen atom; and R.sup.4 is, for example, a hydrogen atom or a C.sub.1C.sub.12 alkyl group.] The derivative or the salt has an excellent pest control effect.

Claims

1. An alkyl phenyl sulfide derivative represented by the general formula [I] or an agriculturally acceptable salt thereof ##STR00146## wherein n is an integer of 0, 1 or 2, R.sup.1 is a C.sub.1-C.sub.6 haloalkyl group (the group excludes 2-bromoethyl group and 3-bromopropyl group), a C.sub.2-C.sub.8 alkenyl group (the group excludes allyl group), a C.sub.2-C.sub.8 haloalkenyl group, a C.sub.2-C.sub.6 alkynyl group, a C.sub.2-C.sub.6 haloalkynyl group, a branched C.sub.4-C.sub.6 alkyl group (the group excludes isobutyl group), a C.sub.3-C.sub.6 cycloalkyl C.sub.1-C.sub.6 alkyl group or a C.sub.3-C.sub.6 halocycloalkyl C.sub.1-C.sub.6 alkyl group, R.sup.2 is a halogen atom, a C.sub.1-C.sub.6 alkyl group, a C.sub.1-C.sub.6 haloalkyl group, a C.sub.3-C.sub.6 cycloalkyl group, a C.sub.3-C.sub.6 halocycloalkyl group, a C.sub.1-C.sub.6 haloalkoxy group, a cyano group or a nitro group, R.sup.3 is a hydrogen atom, a halogen atom, a C.sub.1-C.sub.6 alkyl group or a C.sub.1-C.sub.6 haloalkyl group.

2. The alkyl phenyl sulfide derivative or an agriculturally acceptable salt thereof, according to claim 1, wherein R.sup.2 in the general formula [I] is a halogen atom, a C.sub.1-C.sub.6 alkyl group, a C.sub.1-C.sub.6 haloalkyl group or a cyano group.

3. The alkyl phenyl sulfide derivative or an agriculturally acceptable salt thereof, according to claim 1, wherein R.sup.3 in the general formula [I] is a hydrogen atom, a halogen atom or a C.sub.1-C.sub.6 alkyl group.

4. An alkyl phenyl sulfide derivative or an agriculturally acceptable salt thereof, according to claim 2, wherein R.sup.3 in the general formula [I] is a hydrogen atom, a halogen atom or a C.sub.1-C.sub.6 alkyl group.

5. A pest control agent comprising an alkyl phenyl sulfide derivative or an agriculturally acceptable salt thereof, according to claim 3, as an active ingredient; and at least one additive component.

6. A pest control agent comprising: an alkyl phenyl sulfide derivative or an agriculturally acceptable salt thereof as an active ingredient, wherein the alkyl phenyl sulfide derivative is represented by the general formula [I] or the agriculturally acceptable salt thereof ##STR00147## wherein n is an integer of 0, 1 or 2, R.sup.1 is a C.sub.1-C.sub.6 haloalkyl group (the group excludes 2-bromoethyl group), a C.sub.2-C.sub.8 alkenyl group (the group excludes allyl group), a C.sub.2-C.sub.8 haloalkenyl group, a C.sub.2-C.sub.6 alkynyl group, a C.sub.2-C.sub.6 haloalkynyl group, a branched C.sub.4-C.sub.6 alkyl group (the group excludes isobutyl group), a C.sub.3-C.sub.6 cycloalkyl C.sub.1-C.sub.6 alkyl group or a C.sub.3-C.sub.6 halocycloalkyl C.sub.1-C.sub.6 alkyl group, R.sup.2 is a halogen atom, a C.sub.1-C.sub.6 alkyl group, a C.sub.1-C.sub.6 haloalkyl group, a C.sub.3-C.sub.6 cycloalkyl group, a C.sub.3-C.sub.6 halocycloalkyl group, a C.sub.1-C.sub.6 haloalkoxy group, a cyano group or a nitro group, R.sup.3 is a hydrogen atom, a halogen atom, a C.sub.1-C.sub.6 alkyl group or a C.sub.1-C.sub.6 haloalkyl group.

7. An alkyl phenyl sulfide derivative represented by the general formula [I] or an agriculturally acceptable salt thereof ##STR00148## wherein n is an integer of 0, 1 or 2, wherein R.sup.1 in the general formula [I] is a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a 3,3,3-trifluoropropyl group, a pentafluoroethyl group, a 1,2,2,2-tetrafluoroethyl group, a 2-chloro-2,2-difluoroethyl group, a 2,2,3,3-tetrafluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a 3,3-dichloroallyl group, a propargyl group, a cyclopropylmethyl group or a (2,2-difluorocyclopropyl)methyl group, wherein R.sup.2 is a halogen atom, a C.sub.1-C.sub.6 alkyl group, a C.sub.1-C.sub.6 haloalkyl group, a C.sub.3-C.sub.6 cycloalkyl group, a C.sub.3-C.sub.6 halocycloalkyl group, a C.sub.1-C.sub.6 haloalkoxy group, a cyano group or a nitro group, and wherein R.sup.3 is a hydrogen atom, a halogen atom, a C.sub.1-C.sub.6 alkyl group or a C.sub.1-C.sub.6 haloalkyl group.

8. The alkyl phenyl sulfide derivative or an agriculturally acceptable salt thereof, according to claim 7, wherein R.sup.2 in the general formula [I] is a halogen atom, a C.sub.1-C.sub.6 alkyl group, a C.sub.1-C.sub.6 haloalkyl group or a cyano group.

9. The alkyl phenyl sulfide derivative or an agriculturally acceptable salt thereof, according to claim 7, wherein R.sup.3 in the general formula [I] is a hydrogen atom, a halogen atom or a C.sub.1-C.sub.6 alkyl group.

10. A pest control agent which contains, as an active ingredient, an alkyl phenyl sulfide derivative or an agriculturally acceptable salt thereof, according to claim 7.

Description

EXAMPLES

Example 1

Production of 2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenol (Present Compound No. C-0001)

(1) To 300 ml of toluene were added 32.0 g (119 mmol) of 2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl boronic acid produced by the method described in PCT International Publication No. WO 2007/034755 and 15.4 g (131 mmol) of N-methylmorpholine-N-oxide, followed by refluxing for 1 hour under heating. The reaction mixture was allowed to cool to room temperature. The solvent was distilled off under reduced pressure. The residue was subjected to extraction with ethyl acetate. The organic phase obtained was washed with water and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: a mixed solvent of n-hexane:ethyl acetate=4:1), to obtain 25.5 g (yield: 89%) of an intended product.

(2) .sup.1H-NMR (300 MHz, CDCl.sub.3/TMS (ppm))

(3) 2.38 (3H, s), 3.32 (2H, q), 5.28 (1H, brs),

(4) 6.95 (1H, d), 7.22 (1H, d)

Example 2

Production of 4-methyl-3-(2,2,2-trifluoroethylthio)phenol (Present Compound No. C-0005)

(5) 49.7 g (225 mmol) of 4-methyl-3-(2,2,2-trifluoroethylthio)aniline was suspended in 500 ml of a 15% aqueous sulfuric acid solution. Thereinto was dropwise added an aqueous solution obtained by dissolving 18.6 g (270 mmol) of sodium nitrite in 100 ml of water, at 0 to 5 C. with ice-cooling. After the completion of the dropwise addition, the mixture was stirred for 1 hour with the temperature being kept. The reaction mixture was gradually dropped at 120 C. into a solution obtained by dissolving 71.8 g (450 mmol) of anhydrous copper sulfate in 400 ml of 60% sulfuric acid. The mixture was allowed to cool to room temperature and subjected to extraction with ethyl acetate. The organic phase obtained was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crude product obtained was purified by column chromatography (developing solvent: a mixed solvent of n-hexane:ethyl acetate=10:1), to obtain 19 g (yield: 38%) of an intended product.

(6) .sup.1H-NMR (400 MHz, CDCl.sub.3/TMS (ppm))

(7) 2.36 (3H, s), 3.38 (2H, q), 5.61 (1H, brs),

(8) 6.69 (1H, dd), 6.93 (1H, s), 7.03 (1H, d)

Example 3

Production of 5,5-dimethylhexyl-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl] ether (Present Compound No. A-0085)

(9) To 70 ml of tetrahydrofuran were added 1.6 g (6.7 mmol) of 2-fluoro-4-methyl-3-(2,2,2-trifluoroethylthio)phenol, 1.7 g (13 mmol) of 5,5-dimethylhexanol, 2.0 g (9.9 mmol) of diisopropyl azodicarboxylate and 2.6 g (9.9 mmol) of triphenylphosphine. A reaction was carried out at room temperature for 16 hours. After confirmation of the completion of the reaction, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: a mixed solvent of n-hexane:ethyl acetate=4:1), to obtain 2.3 g (yield: 97%) of an intended product.

(10) Incidentally, the production method of 5,5-dimethylhexanol is described in, for example, J. Am. Chem. Soc., 119 (29), 6909 (1997).

(11) .sup.1H-NMR (300 MHz, CDCl.sub.3/TMS (ppm))

(12) 0.88 (9H, s), 1.19-1.27 (2H, m), 1.36-1.48 (2H, m),

(13) 1.77 (2H, quint), 2.41 (3H, s), 3.29 (2H, q),

(14) 4.01 (2H, t), 6.95 (1H, d), 7.15 (1H, d)

Example 4

Production of 5,5-dimethylhexyl-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfinyl)phenyl] ether (Present Compound No. A-0086)

(15) In 70 ml of chloroform was dissolved 2.3 g (6.5 mmol) of 5,5-dimethylhexyl-{2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl ether. Thereto was added, in portions in about 10 minutes, 1.5 g (6.5 mmol) of 3-chloroperbenzoic acid (purity: about 75%) at room temperature. A reaction was carried out for 1 hour. After confirmation of the completion of the reaction, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: a mixed solvent of n-hexane:ethyl acetate:triethylamine=5:1:0.01), to obtain 2.2 g (yield: 92%) of an intended product.

(16) .sup.1H-NMR (300 MHz, CDCl.sub.3/TMS (ppm))

(17) 0.89 (9H, s), 1.19-1.27 (2H, m), 1.37-1.49 (2H, m),

(18) 1.81 (2H, quint), 2.31 (3H, s), 3.30-3.48 (2H, m),

(19) 4.10 (2H, t), 6.98 (1H, d), 7.55 (1H, d)

Example 5

Production of 5-trifluoromethylthiopentyl-[4-methyl-3-(2,2,2-trifluoroethylthio)phenyl] ether (Present Compound No. A-0438)

(20) To 100 ml of tetrahydrofuran were added 1.5 g (4.3 mmol) of 5-thiocyanatopentyl-{4-methyl-3-(2,2,2-trifluroethylthio)phenyl} ether and 1.8 g (13 mmol) of trifluoromethyltrimetylsilane. Thereto was added, at 0 C., 5 ml (5.0 mmol) of a tetra-n-butylammonium fluoridetetrahydrofuran (1 mol/liter) solution. A reaction was carried out for 1 hour. After confirmation of the completion of the reaction, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: a mixed solvent of n-hexane:ethyl acetate=10:1), to obtain 1.3 g (yield: 77%) of an intended product.

(21) .sup.1H-NMR (300 MHz, CDCl.sub.3/TMS (ppm))

(22) 1.56-1.64 (2H, m), 1.73-1.85 (4H, m), 2.38 (3H, s),

(23) 2.91 (2H, t), 3.40 (2H, q), 3.94 (2H, t), 6.75 (1H, dd), 7.00 (1H, d), 7.11 (1H, d)

Example 6

Production of 5-chloropentyl-[4-methyl-3-(2,2,2-trifluoroethylthio)phenyl] ether (Present Compound No. A-0279)

(24) To 100 ml of acetonitrile were added 2.5 g (11 mmol) of 4-methyl-3-(2,2,2-trifluoroethylthio)phenol, 2.5 g (13 mmol) of 1-bromo-5-chloropentane, 1.9 g (14 mmol) of potassium carbonate and 0.35 g (1.1 mmol) of tetra-n-butylammonium bromide. The mixture was refluxed for 5 hours under heating and then allowed to cool to room temperature. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: a mixed solvent of n-hexane:ethyl acetate=10:1), to obtain 2.9 g (yield: 79%) of an intended product.

(25) .sup.1H-NMR (300 MHz, CDCl.sub.3/TMS (ppm))

(26) 1.56-1.66 (2H, m), 1.74-1.93 (4H, m), 2.38 (3H, s),

(27) 3.36 (2H, q), 3.56 (2H, t), 3.94 (2H, t), 6.74 (1H, d), 7.00 (1H, s), 7.09 (1H, d)

Example 7

Production of 5-thiocyanatopentyl-[4-methyl-3-(2,2,2-trifluoroethylthio)phenyl] ether (Present Compound No. A-0672)

(28) To 100 ml of ethanol were added 2.0 g (6.1 mmol) of 5-chloropentyl-{4-methyl-3-(2,2,2-trifluoroethylthio)phenyl} ether, 4.0 g (41 mmol) of potassium thiocyanate and 0.10 g (0.61 mmol) of potassium iodide. The mixture was refluxed for 10 hours under heating and then allowed to cool to room temperature. The solvent was distilled off under reduced pressure. To the residue was added ethyl acetate to conduct extraction. The organic phase obtained was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: a mixed solvent of n-hexane:ethyl acetate=10:1), to obtain 1.8 g (yield: 84%) of an intended product.

(29) .sup.1H-NMR (300 MHz, CDCl.sub.3/TMS (ppm))

(30) 1.53-1.68 (2H, m), 1.76-1.87 (4H, m), 2.38 (3H, s),

(31) 3.00 (2H, t), 3.39 (2H, q), 3.97 (2H, t), 6.74 (1H, d), 7.00 (1H, s), 7.13 (1H, d)

Example 8

Production of 5-trifluoromethylthiopentyl-[4-methyl-3-(2,2,2-trifluoroethylsulfinyl)phenyl] ether (Present Compound No. A-0439)

(32) In 100 ml of chloroform was dissolved 0.98 g (2.5 mmol) of 5-trifluoromethylthiopentyl-{4-methyl-5-(2,2,2-trifluoroethylthio)phenyl} ether. Thereto was added, in portions in about 10 minutes, 0.58 g (2.5 mmol) of 3-chloroperbenzoic acid (purity: about 75%) at room temperature. A reaction was carried out for 1 hour. After confirmation of the completion of the reaction, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: a mixed solvent of n-hexane:ethyl acetate:triethylamine=5:1:0.01), to obtain 0.78 g (yield: 77%) of an intended product.

(33) .sup.1H-NMR (300 MHz, CDCl.sub.3/TMS (ppm))

(34) 1.57-1.64 (2H, m), 1.73-1.88 (4H, m), 2.31 (3H, s),

(35) 2.92 (2H, t), 2.32-3.45 (2H, m), 4.05 (2H, t),

(36) 6.97 (1H, dd), 7.15 (1H, d), 7.48 (1H, d)

Example 9

Production of 4-chloro-2-fluoro-5-(2,2,2-trifluoroethylthio)phenol (Present Compound No. C-0003)

(37) To 200 ml of toluene were added 33 g (114 mmol) of 4-chloro-2-fluoro-5-(2,2,2-trifluoroethylthio)phenyl boronic acid and 16 g (137 mmol) of N-methylmorpholine-N-oxide. The mixture was refluxed for 1 hour under heating. After confirmation of the completion of the reaction, the mixture was allowed to cool to room temperature. Then the solvent was distilled off under reduced pressure, and the residue was subjected to extraction with ethyl acetate. The organic phase obtained was washed with water and dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 24.5 g (yield: 82%) of an intended product.

(38) .sup.1H-NMR (300 MHz, CDCl.sub.3/TMS (ppm))

(39) 3.43 (2H, q), 5.31 (1H, d), 7.16 (1H, d), 7.31 (1H, d)

Example 10

Production of 5-bromopentyl-[4-chloro-2-fluoro-5-(2,2,2-trifluoroethylthio)phenyl] ether (Present Compound No. A-0273)

(40) To 60 ml of acetonitrile were added 3.0 g (11.5 mmol) of 4-chloro-2-fluoro-5-(2,2,2-trifluoroethylthio)phenol, 13.2 g (57.4 mmol) of 1,5-dibromopentane, 2.1 g (15.0 mmol) of potassium carbonate and 0.37 g (1.15 mmol) of tetra-n-butylammonium bromide. The mixture was refluxed for 1.5 hour under heating. The mixture was allowed to cool to room temperature, and insoluble matters were removed by filtration. Then the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: a mixed solvent of n-hexane:ethyl acetate=20:1), to obtain 4.2 g (yield: 89%) of an intended product.

(41) .sup.1H-NMR (400 MHz, CDCl.sub.3/TMS (ppm))

(42) 1.59-1.69 (2H, m), 1.82-1.99 (4H, m), 3.36-3.47 (4H, m), 4.03 (2H, t), 7.20 (1H, d), 7.23 (1H, d)

Example 11

Production of 5-thiocyanatopentyl-[4-chloro-2-fluoro-5-(2,2,2-trifluoroethylthio)phenyl] ether (Present Compound No. A-0670)

(43) To 60 ml of ethanol were added 4.2 g (10.3 mmol) of 5-bromopentyl-[4-chloro-2-fluoro-5-(2,2,2-trifluoroethylthio)phenyl] ether and 5.0 g (51.5 mmol) of potassium thiocyanate. The mixture was refluxed for 4 hours under heating. The mixture was allowed to cool to room temperature, and the solvent was distilled off under reduced pressure. Then extraction was conducted by adding water and ethyl acetate. The organic phase obtained was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: a mixed solvent of n-hexane:ethyl acetate=10:1), to obtain 3.9 g (yield: 98%) of an intended product.

(44) .sup.1H-NMR (400 MHz, CDCl.sub.3/TMS (ppm))

(45) 1.59-1.69 (2H, m), 1.82-1.99 (4H, m), 2.99 (2H, t)

(46) 3.42 (2H, q), 4.04 (2H, t), 7.20 (1H, d), 7.23 (1H, d)

Example 12

Production of 5-trifluoromethylthiopentyl-[4-chloro-2-fluoro-5-(2,2,2-trifluoroethylthio)phenyl] ether (Present Compound No. A-0433)

(47) To 60 ml of tetrahydrofuran were added 3.9 g (10.1 mmol) of 5-thiocyanatopentyl-[4-chloro-2-fluoro-5-(2,2,2-trifluoroethylthio)phenyl] ether and 4.5 g (31.6 mmol) of trifluoromethyltrimethylsilane. Thereto was added 1.0 ml (1.04 mmol) of tetrahydrofuran solution (1 mol/liter) of tetra-n-butylammonium fluoride at 0 C., and reaction was carried out. The mixture was stirred overnight at room temperature. Then, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: a mixed solvent of n-hexane:ethyl acetate=20:1), to obtain 2.60 g (yield: 60%) of an intended product.

(48) .sup.1H-NMR (400 MHz, CDCl.sub.3/TMS (ppm))

(49) 1.58-1.66 (2H, m), 1.73-1.89 (4H, m), 2.92 (2H, t),

(50) 3.41 (2H, q), 4.03 (2H, t), 7.21 (1H, d), 7.23 (1H, d)

Example 13

Production of 5-trifluoromethylthiopentyl-[4-chloro-2-fluoro-5-(2,2,2-trifluoroethylsulfinyl)phenyl] ether (Present Compound No. A-0434)

(51) In 50 ml of chloroform was dissolved 2.60 g (6.03 mmol) of 5-trifluoromethylthiopentyl-[4-chloro-2-fluoro-5-(2,2,2-trifluoroethylthio)phenyl] ether. Thereto was added 1.39 g (6.04 mmol) of 3-chloroperbenzoic acid (purity: about 75%) at 0 C., and the mixture was stirred overnight at room temperature. Then, the solvent was distilled off under reduced pressure, 1 ml of triethylamine was added to the residue, and the residue was purified by silica gel column chromatography (developing solvent: a mixed solvent of n-hexane:ethyl acetate=5:1), to obtain 2.06 g (yield: 76%) of an intended product.

(52) .sup.1H-NMR (400 MHz, CDCl.sub.3/TMS (ppm))

(53) 1.57-1.66 (2H, m), 1.74-1.93 (4H, m), 2.92 (2H, t),

(54) 3.30-3.43 (1H, m), 3.66-3.78 (1H, m), 4.13 (2H, t),

(55) 7.21 (1H, d), 7.54 (1H, d)

Example 14

Production of 2,4-dichloro-5-(2,2,2-trifluoroethylthio)phenol (Present Compound No. C-0014)

(56) To 150 ml of toluene was added 29.0 g (50% aqueous solution, 124 mmol) of N-methylmorpholine-N-oxide, and dehydration was conducted by heating under reflux for 1 hour. To the reaction mixture was dropwise added 31.5 g (103 mmol) of 2,4-dichloro-5-(2,2,2-trifluoroethylthio)phenylboronic acid dissolved in ethyl acetate, and the mixture was refluxed for 3 hours under heating. Then, the mixture was allowed to cool to room temperature, and 10% aqueous hydrochloric acid was added, followed by extraction with ethyl acetate. The organic phase obtained was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: a mixed solvent of n-hexane:ethyl acetate=10:1), to obtain 27.2 g (yield: 95%) of an intended product.

(57) .sup.1H-NMR (300 MHz, CDCl.sub.3/TMS (ppm))

(58) 3.48 (2H, q), 5.70 (1H, s), 7.20 (1H, s), 7.41 (1H, s)

Example 15

Production of 6-bromohexyl-[2,4-dichloro-5-(2,2,2-trifluoroethylthio)phenyl] ether (Present Compound No. A-0283)

(59) To 30 ml of acetonitrile were added 1.0 g (3.61 mmol) of 2,4-dichloro-5-(2,2,2-trifluoroethylthio)phenol, 3.5 g (14.4 mmol) of 1,6-dibromohexane, 0.65 g (15.0 mmol) of potassium carbonate and 0.12 g (0.37 mmol) of tetra-n-butylammonium bromide. The mixture was refluxed for 3 hours under heating. The mixture was allowed to stand at room temperature, and insoluble matters were removed by filtration. Then the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: a mixed solvent of n-hexane:ethyl acetate=20:1), to obtain 1.51 g (yield: 95%) of an intended product.

(60) .sup.1H-NMR (400 MHz, CDCl.sub.3/TMS (ppm))

(61) 1.50-1.60 (4H, m), 1.81-1.93 (4H, m),

(62) 3.39-3.49 (4H, m), 4.02 (2H, t), 7.13 (1H, s),

(63) 7.45 (1H, s)

Example 16

Production of 6-thiocyanatohexyl-[2,4-dichloro-5-(2,2,2-trifluoroethylthio)phenyl] ether (Present Compound No. A-0678)

(64) In 30 ml of ethanol were added 1.51 g (3.43 mmol) of 6-bromohexyl-[2,4-dichloro-5-(2,2,2-trifluoroethylthio)phenyl] ether and 1.67 g (17.2 mmol) of potassium thiocyanate. The mixture was refluxed for 3 hours under heating. The mixture was allowed to cool to room temperature, and the solvent was distilled off under reduced pressure. Then extraction was conducted by adding ethyl acetate and water. The organic phase obtained was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: a mixed solvent of n-hexane:ethyl acetate=10:1), to obtain 1.04 g (yield: 73%) of an intended product.

(65) .sup.1H-NMR (400 MHz, CDCl.sub.3/TMS (ppm))

(66) 1.50-1.62 (4H, m), 1.83-1.92 (4H, m), 2.96 (2H, t),

(67) 3.45 (2H, q), 4.03 (2H, t), 7.13 (1H, s), 7.46 (1H, s)

Example 17

Production of 6-trifluoromethylthiohexyl-[2,4-dichloro-5-(2,2,2-trifluoroethylthio)phenyl] ether (Present Compound No. A-0478)

(68) To 30 ml of tetrahydrofuran were added 1.04 g (2.49 mmol) of 6-thiocyanatohexyl-[2,4-dichloro-5-(2,2,2-trifluoroethylthio)phenyl] ether and 1.06 g (7.45 mmol) of trifluoromethyltrimethylsilane. Thereto was added 0.25 ml (concentration: 1 mol/liter, 0.25 mmol) of tetrahydrofuran solution of tetra-n-butylammonium fluoride at 0 C., and reaction mixture was stirred for 2 hours at room temperature. Then, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: a mixed solvent of n-hexane:ethyl acetate=20:1), to obtain 0.73 g (yield: 64%) of an intended product.

(69) .sup.1H-NMR (300 MHz, CDCl.sub.3/TMS (ppm))

(70) 1.44-1.62 (4H, m), 1.67-1.90 (4H, m), 2.90 (2H, t),

(71) 3.44 (2H, q), 4.02 (2H, t), 7.13 (1H, s), 7.46 (1H, s)

Example 18

Production of 6-trifluoromethylthiohexyl-[2,4-dichloro-5-(2,2,2-trifluoroethylsulfinyl)phenyl] ether (Present Compound No. A-0479)

(72) In 30 ml of chloroform was dissolved 0.53 g (1.15 mmol) of 6-trifluoromethylthiohexyl-[2,4-dichloro-5-(2,2,2-trifluoroethylthio)phenyl] ether. Thereto was added 0.26 g (1.13 mmol) of 3-chloroperbenzoic acid (purity: about 75%) at 0 C., and the mixture was stirred for 3 hours at room temperature. Then, the solvent was distilled off under reduced pressure, 0.5 ml of triethylamine was added to the residue, and the residue was purified by silica gel column chromatography (developing solvent: a mixed solvent of n-hexane:ethyl acetate=5:1), to obtain 0.41 g (yield: 75%) of an intended product.

(73) .sup.1H-NMR (300 MHz, CDCl.sub.3/TMS (ppm))

(74) 1.48-1.64 (4H, m), 1.63-1.94 (4H, m), 2.90 (2H, t),

(75) 3.28-3.44 (1H, m), 3.68-3.81 (1H, m), 4.13 (2H, t)

(76) 7.47 (1H, s), 7.48 (1H, s)

Example 19

Production of 2,4-dichloro-5-(2,2,2-trifluoroethylsulfinyl)phenol (Present Compound No. C-0015)

(77) In 80 ml of chloroform was dissolved 10.0 g (36.08 mmol) of 2,4-dichloro-5-(2,2,2-trifluoroethylthio)phenol. Thereto was added 9.80 g (39.75 mmol) of 3-chloroperbenzoic acid (purity: about 70%) under ice cooling, and the mixture was stirred for 30 minutes at room temperature. Then, saturated aqueous solution of sodium thiosulfate was added to the reaction mixture to decompose excess peroxide. Thereafter, the solvent was distilled off under reduced pressure, and extraction was conducted by adding ethyl acetate and water. The organic phase obtained was washed by aqueous potassium carbonate solution and saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, to obtain 9.30 g (yield: 88%) of an intended product.

(78) .sup.1H-NMR (300 MHz, CDCl.sub.3/TMS (ppm))

(79) 3.30-3.44 (1H, m), 3.66-3.80 (1H, m), 7.40 (1H, s),

(80) 7.61 (1H, s)

Example 20

Production of 2-(4-trifluoromethylphenyl)ethyl-[2,4-dichloro-5-(2,2,2-trifluoroethylsulfinyl)phenyl] ether (Present Compound No. A-0767)

(81) In 30 ml of tetrahydrofuran were dissolved 0.5 g (1.71 mmol) of 2,4-dichloro-5-(2,2,2-trifluoroethylsulfinyl)phenol, 0.33 g (1.74 mmol) of 2-(4-trifluoromethylphenyl)ethanol and 0.49 g (1.87 mmol) of triphenylphosphine. Thereto was added 0.38 g (1.87 mmol) of diisopropyl azodicarboxylate at room temperature, and the reaction mixture was stirred for 16 hours. Then, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: a mixed solvent of n-hexane:ethyl acetate=5:1), to obtain 0.41 g (yield: 52%) of an intended product.

(82) .sup.1H-NMR (300 MHz, CDCl.sub.3/TMS (ppm))

(83) 3.21-3.40 (3H, m), 3.64-3.79 (1H, m), 4.31-4.36 (2H, m), 7.44-7.46 (4H, m), 7.58 (2H, d)

Example 21

Production of 2,4-dimethyl-5-(2,2,2-trifluoroethylthio)phenol (Present Compound No. C-0017)

(84) To 200 ml of toluene were added 20.24 g (58.5 mmol) of [2,4-dimethyl-5-(2,2,2-trifluoroethylthio)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (a compound described in PCT International Publication No. WO 2012/176856 as Compound No. 55-47) and 8.22 g (70.16 mmol) of N-methylmorpholine-N-oxide. The mixture was refluxed for 2 hours under heating. The reaction mixture was allowed to cool to room temperature, washed and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (developing solvent: a mixed solvent of n-hexane:ethyl acetate=20:1), to obtain 10.54 g (yield: 76%) of an intended product.

(85) .sup.1H-NMR (300 MHz, CDCl.sub.3/TMS (ppm))

(86) 2.20 (3H, s), 2.36 (3H, s), 3.32 (2H, q), 4.78 (1H, s), 6.93 (1H, s), 6.98 (1H, s)

Example 22

Production of 2,4-dimethyl-5-(2,2,2-trifluoroethylsulfinyl)phenol (Present Compound No. C-0018)

(87) In 30 ml of chloroform was dissolved 2.60 g (11.0 mmol) of 2,4-dimethyl-5-(2,2,2-trifluoroethylthio)phenol. Thereto was added 3.25 g (13.18 mmol) of 3-chloroperbenzoic acid (purity: about 70%) under ice cooling, and the mixture was stirred for 30 minutes at room temperature. Then, saturated aqueous solution of sodium thiosulfate was added to the reaction mixture to decompose excess peroxide. Thereafter, the solvent was distilled off under reduced pressure, and phase separation was conducted by adding ethyl acetate and water. The organic phase obtained was washed by aqueous potassium carbonate solution and saturated aqueous sodium chloride solution, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure, to obtain 2.13 g (yield: 77%) of an intended product.

(88) .sup.1H-NMR (300 MHz, CDCl.sub.3/TMS (ppm))

(89) 2.25 (6H, s), 3.35-3.53 (2H, m), 6.98 (1H, s),

(90) 7.63 (1H, s), 7.69 (1H, s)

Example 23

Production of 2-(4-trifluoromethoxyphenyl)ethyl-[2,4-dimethyl-5-(2,2,2-trifluoroethylsulfinyl)phenyl] ether (Present Compound No. A-0783)

(91) In 30 ml of tetrahydrofuran were dissolved 0.3 g (1.19 mmol) of 2,4-dimethyl-5-(2,2,2-trifluoroethylsulfinyl)phenol, 0.29 g (1.41 mmol) of 2-(4-trifluoromethoxyphenyl)ethanol and 0.41 g (1.56 mmol) of triphenylphosphine. Thereto was added 0.31 g (1.53 mmol) of diisopropyl azodicarboxylate at room temperature, and stirred for 16 hours. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: a mixed solvent of n-hexane:ethyl acetate=5:1), and the residue was washed with n-hexane, to obtain 0.21 g (yield: 40%) of an intended product.

(92) .sup.1H-NMR (300 MHz, CDCl.sub.3/TMS (ppm))

(93) 2.18 (3H, s), 2.26 (3H, s), 3.13 (2H, t),

(94) 3.32-3.41 (2H, m), 4.24-4.25 (2H, m),

(95) 6.70 (1H, s), 7.16 (2H, d), 7.30-7.36 (3H, m)

Example 24

Production of 6-bromohexyl-[2,4-dimethyl-5-(2,2,2-trifluoroethylthio)phenyl] ether (Present Compound No. A-0284)

(96) To 60 ml of acetonitrile were added 1.14 g (4.83 mmol) of 2,4-dimethyl-5-(2,2,2-trifluoroethylthio)phenol, 4.71 g (19.31 mmol) of 1,6-dibromohexane, 0.73 g (5.28 mmol) of potassium carbonate and catalytic amount of tetra-n-butylammonium bromide. The mixture was refluxed for 3 hours under heating. The mixture was allowed to cool to room temperature, and insoluble matters were removed by filtration. Then the solvent of filtrate was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: a mixed solvent of n-hexane:ethyl acetate=40:1-20:1), to obtain 1.87 g (yield: 97%) of an intended product.

(97) .sup.1H-NMR (300 MHz, CDCl.sub.3/TMS (ppm))

(98) 1.53 (4H, m), 1.70-2.03 (4H, m), 2.17 (3H, s),

(99) 2.38 (3H, s), 3.26-3.43 (4H, m), 3.94 (2H, t),

(100) 6.96 (1H, s), 6.99 (1H, s)

Example 25

Production of 6-thiocyanatohexyl-[2,4-dimethyl-5-(2,2,2-trifluoroethylthio)phenyl] ether (Present Compound No. A-0679)

(101) To 60 ml of ethanol were added 1.87 g (4.68 mmol) of 6-bromohexyl-[2,4-dimethyl-5-(2,2,2-trifluoroethylthio)phenyl] ether and 2.28 g (23.46 mmol) of potassium thiocyanate. The mixture was refluxed for 8 hours under heating. The mixture was allowed to cool to room temperature, and the solvent was distilled off under reduced pressure. Then extraction was conducted by adding ethyl acetate and water. The organic phase obtained was washed with water, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: a mixed solvent of n-hexane:ethyl acetate=20:1), to obtain 1.37 g (yield: 77%) of an intended product.

(102) .sup.1H-NMR (300 MHz, CDCl.sub.3/TMS (ppm))

(103) 1.53-1.54 (4H, m), 1.82-1.87 (4H, m), 2.17 (3H, s)

(104) 2.38 (3H, s), 2.96 (2H, t), 3.31 (2H, q), 3.94 (2H, t)

(105) 6.96 (1H, s), 6.70 (1H, s)

Example 26

Production of 6-trifluoromethylthiohexyl-[2,4-dimethyl-5-(2,2,2-trifluoroethylthio)phenyl] ether (Present Compound No. A-0480)

(106) To 100 ml of tetrahydrofuran were added 1.37 g (3.63 mmol) of 6-thiocyanatohexyl-[2,4-dimethyl-5-(2,2,2-trifluoroethylthio)phenyl] ether and 1.29 g (9.07 mmol) of trifluoromethyltrimethylsilane. Thereto was added 0.4 ml (0.4 mmol) of tetrahydrofuran solution of tetra-n-butylammonium fluoride (1 mol/liter) at 0 C., and the mixture was stirred for 4 hours at 0 C. Then, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: a mixed solvent of n-hexane:ethyl acetate=20:1), to obtain 1.36 g (yield: 89%) of an intended product.

(107) .sup.1H-NMR (300 MHz, CDCl.sub.3/TMS (ppm))

(108) 1.49-1.53 (4H, m), 1.71-1.82 (4H, m), 2.17 (3H, s)

(109) 2.38 (3H, s), 2.90 (2H, t), 3.30 (2H, q), 3.94 (2H, t)

(110) 6.96 (1H, s), 6.70 (1H, s)

Example 27

Production of 6-trifluoromethylthiohexyl-[2,4-dimethyl-5-(2,2,2-trifluoroethylsulfinyl)phenyl]ether (Present Compound No. A-0481)

(111) In 40 ml of chloroform was dissolved 1.36 g (3.23 mmol) of 6-trifluoromethylthiohexyl-[2,4-dimethyl-5-(2,2,2-trifluoroethylthio)phenyl]ether. Thereto was added 0.67 g (2.72 mmol) of 3-chloroperbenzoic acid (purity: about 70%) under ice cooling, and the mixture was stirred for 30 minutes at room temperature. Then, saturated aqueous solution of sodium thiosulfate was added to the reaction mixture to decompose excess peroxide. Thereafter, the solvent was distilled off under reduced pressure, and extraction was conducted by adding ethyl acetate and water. The organic phase obtained was washed by aqueous potassium carbonate solution and saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (developing solvent: a mixed solvent of n-hexane:ethyl acetate=5:1), to obtain 0.87 g (yield: 62%) of an intended product.

(112) .sup.1H-NMR (400 MHz, CDCl.sub.3/TMS (ppm))

(113) 1.50-1.52 (4H, m), 1.72-1.85 (4H, m), 2.23 (3H, s),

(114) 2.28 (3H, s), 2.90 (2H, t), 3.28-3.47 (2H, m),

(115) 4.04 (2H, t), 7.01 (1H, s), 7.36 (1H, s)

Example 28

Production of 5-trifluoromethylthiopentyl-[4-chloro-2-fluoro-5-(2,2,2-trifluoroethylsulfinyl)phenyl]ether optical isomer

(116) An optical active column (internal diameter: 20 mm, length: 250 mm), CHIRAL PAK AD (trade name) manufactured by Daicel Corporation, was equipped with high performance liquid chromatography equipment, and a mixed solvent (hexane:2-propanol=97:3) was perfused as mobile phase. Then, 150 mg of 5-trifluoromethylthiopentyl-[4-chloro-2-fluoro-5-(2,2,2-trifluoroethylsulfinyl)phenyl]ether (racemic mixture) dissolved in 2-propanol was injected, and analysis was conducted in a following conditions.

(117) flow speed: 8.0 ml/minute

(118) temperature: room temperature

(119) detector: ultraviolet absorption detector (254 nm)

(120) As a result, there observed peak 1 (retention time: 17.8 minutes) and peak 2 (retention time: 30.2 minutes), and 70 mg of a compound of respective peaks (both optical purity was 100% e.e.) were isolated. Measurement of respective Reflective Index revealed that Specific Rotation of the component of peak 1 was [].sub.D.sup.25=120.28 (C=0.50/methanol) and Specific Rotation of the component of peak 2 was [].sub.D.sup.25=+119.32 (C=0.50/methanol).

(121) Accordingly, the component of the peak 1 is ()-5-trifluoromethylthiopentyl-[4-chloro-2-fluoro-5-(2,2,2-trifluoroethylsulfinyl)phenyl]ether [()-enantiomer of the present compound No. A-0434], and the component of the peak 2 is (+)-5-trifluoromethylthiopentyl-[4-chloro-2-fluoro-5-(2,2,2-trifluoroethylsulfinyl)phenyl]ether [(+)-enantiomer of the present compound No. A-0434].

Reference Example 1

Production of p-acetotoluidine

(122) 100 g (933.3 mmol) of p-toluidine and 154.8 g (1,120 mmol) of potassium carbonate were dissolved in a mixed solvent of 1,000 ml of ethyl acetate and 500 ml of water. Thereinto was dropped 87.9 g (1,120 mmol) of acetyl chloride with ice-cooling, followed by stirring for 2 hours. Extraction with ethyl acetate was carried out. The organic phase obtained was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The crude crystal obtained was washed with hexane to obtain 130 g (yield: 93%) of p-acetotoluidine.

(123) .sup.1H-NMR (400 MHz, CDCl.sub.3/TMS (ppm))

(124) 2.16 (3H, s), 2.31 (3H, s), 7.11-7.16 (3H, m),

(125) 7.37 (2H, d)

Reference Example 2

Production of 3-chlorosulfonyl-4-methylacetoanilide

(126) 130 g (871 mmol) of p-acetotoluidine was gradually added to 405 g (3,477 mmol) of chlorosulfonic acid at room temperature, followed by stirring at 60 C. for 1 hour. The reaction mixture was allowed to stand at room temperature and then poured into ice water. Extraction with ethyl acetate was conducted. The organic phase obtained was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 162 g (yield: 75%) of 3-chlorosulfonyl-4-methylacetoanilide.

(127) .sup.1H-NMR (300 MHz, CDCl.sub.3/TMS (ppm))

(128) 2.22 (3H, s), 2.73 (3H, s), 7.37 (2H, d),

(129) 7.50 (1H, brs), 8.00 (1H, s), 8.02 (1H, d)

Reference Example 3

Production of 3-acetylthio-4-methylacetoanilide

(130) 162 g (654 mmol) of 3-chlorosulfonyl-4-methylacetoanilide was dissolved in 700 ml of acetic acid. Thereto were added 30 g (983 mmol) of red phosphorus and 1.7 g (6.6 mmol) of iodine, followed by stirring for 5 hours under heating and refluxing. The reaction mixture was allowed to cool to room temperature and then filtered through Celite. The filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate. The solution was washed with an aqueous sodium thiosulfate solution and water. The organic phase obtained was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 77.5 g (yield: 53%) of 3-acetylthio-4-methylacetoanilide.

(131) .sup.1H-NMR (300 MHz, CDCl.sub.3/TMS (ppm))

(132) 2.12 (3H, s), 2.30 (3H, s), 2.43 (3H, s),

(133) 7.21-7.28 (2H, m), 7.46 (1H, d), 7.54 (1H, s)

Reference Example 4

Production of 4-methyl-3-mercaptoaniline

(134) 77.5 g (347 mmol) of 3-acetylthio-4-methylacetoanilide was suspended in 700 ml of water. Thereto was added 111 g (2,777 mmol) of sodium hydroxide with stirring. The mixture was stirred for 2 hours under heating and refluxing, and then was allowed to cool to room temperature. The mixture was adjusted to pH 5 using an aqueous hydrochloric acid solution (36%) with stirring under ice-cooling. Extraction with ethyl acetate was conducted. The organic phase obtained was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 47.6 g (yield: 99%) of 4-methyl-3-mercaptoaniline.

(135) .sup.1H-NMR (300 MHz, CDCl.sub.3/TMS (ppm))

(136) 2.21 (3H, s), 3.21 (1H, s), 3.64 (2H, brs),

(137) 6.43 (1H, dd), 6.64 (1H, d), 6.92 (1H, d)

Reference Example 5

Production of 4-methyl-3-(2,2,2-trifluoroethylthio)aniline

(138) 47.6 g (342 mmol) of 4-methyl-3-mercaptoaniline was dissolved in 500 ml of N,N-dimethylformamide. Thereto was added 71 g (513 mmol) of potassium carbonate, followed by stirring for 1 hour. To the reaction mixture were added 4.8 g (31.1 mmol) of Rongalit and 122 g (582 mmol) of 2,2,2-trifluoroidoethane in this order, followed by stirring overnight at room temperature. Water was added and extraction with ethyl acetate was conducted. The organic phase obtained was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The crude product obtained was purified by silica gel column chromatography (developing solvent: a mixed solvent of n-hexane:ethyl acetate=10:1), to obtain 63.8 g (yield: 84%) of 4-methyl-3-(2,2,2-trifluoroethylthio)aniline.

(139) .sup.1H-NMR (300 MHz, CDCl.sub.3/TMS (ppm))

(140) 2.34 (3H, s), 3.37 (2H, q), 3.59 (2H, brs),

(141) 6.56 (1H, dd), 6.82 (1H, d), 6.99 (1H, d)

Reference Example 6

Production of 4-chloro-2-fluoro-5-(2,2,2-trifluoroethylthio)phenyl boronic acid

(142) To 180 ml of diethyl ether was dissolved 15.9 g (49.1 mmol) of (5-bromo-4-chloro-2-fluorophenyl)-2,2,2-trifluoroethylsulfide which was produced by a method described in PCT International Publication No. WO 2012/176856, and the mixture was cooled to 70 C. under nitrogen atmosphere. Thereto was dropwise added 30 ml of n-butyllithium (n-hexane solution, 1.64 mol/liter) for 10 minutes. After 5 minutes, a mixed solution obtained by dissolving 5.1 g (49.1 mmol) of trimethyl borate in 10 ml of diethylether was dropwise added in 10 minutes. Then, the temperature of the reaction mixture was raised to 20 C., 48 g of 20% sulfuric acid was dropwise added, and reaction was conducted in a room temperature for 1.5 hour. To the reaction mixture, ethyl acetate was added, the organic phase obtained was washed with water and aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was washed with n-hexane, to obtain 9.64 g (yield: 68%) of an intended product.

(143) .sup.1H-NMR (400 MHz, CDCl.sub.3/TMS (ppm))

(144) 3.49 (2H, q), 7.30 (1H, d), 8.29 (1H, d)

Reference Example 7

Production of 2,4-dichloro-5-(2,2,2-trifluoroethylthio)phenyl boronic acid

(145) To 700 ml of diethyl ether was dissolved 46.4 g (136 mmol) of (5-bromo-2,4-dichlorophenyl)-2,2,2-trifluoroethylsulfide which was produced by a method described in PCT International Publication No. WO 2012/176856, and the mixture was cooled to 70 C. under nitrogen atmosphere. Thereto was dropwise added 82.7 ml of n-butyllithium (n-hexane solution, 1.64 mol/liter) for 10 minutes. After 5 minutes, a mixed solution obtained by dissolving 14.1 g (136 mmol) of trimethyl borate in 100 ml of diethylether was dropwise added in 10 minutes. Then, the temperature of the reaction mixture was raised to 20 C., 230 ml of 12% (approximately) sulfuric acid was dropwise added, and reaction was conducted in a room temperature for 1.5 hour. The solvent was distilled of under reduced pressure, and to the residue, ethyl acetate was added. The organic phase obtained was washed with water and aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was washed with n-hexane, to obtain 32.58 g (yield: 79%) of an intended product.

(146) .sup.1H-NMR (300 MHz, CDCl.sub.3/TMS (ppm))

(147) 3.49 (2H, q), 5.34 (2H, s), 7.47 (1H, s), 8.11 (1H, s)

(148) The physical properties (melting point, refractive index, .sup.1H-NMR spectrum data and specific rotation of optical isomer) of the present compounds [I] and [I] synthesized based on the Examples (including the physical properties shown in the Examples) are shown in Table 43 to Table 71. Incidentally, the compound Nos. and symbols in Tables have the same meanings as given above.

(149) TABLE-US-00043 TABLE 43 Compound No. Physical Property A-0001 Reflactive Index (n.sub.D.sup.20) 1.4922 A-0004 Reflactive Index (n.sub.D.sup.20) 1.5072 A-0005 Melting Point ( C.) 140-141 A-0006 Reflactive Index (n.sub.D.sup.20) 1.4819 A-0007 Melting Point ( C.) 89-92 A-0012 Reflactive Index (n.sub.D.sup.20) 1.5055 A-0013 Melting Point ( C.) 87-89 A-0014 Reflactive Index (n.sub.D.sup.20) 1.4827 A-0015 Melting Point ( C.) 58-60 A-0017 Reflactive Index (n.sub.D.sup.20) 1.5016 A-0018 Melting Point ( C.) 87-88 A-0022 Reflactive Index (n.sub.D.sup.20) 1.4893 A-0023 Melting Point ( C.) 53-54 A-0024 Reflactive Index (n.sub.D.sup.20) 1.5008 A-0025 Melting Point ( C.) 97-99 A-0027 Reflactive Index (n.sub.D.sup.20) 1.4952 A-0028 Melting Point ( C.) 74-76 A-0030 Reflactive Index (n.sub.D.sup.20) 1.4800 A-0031 Melting Point ( C.) 64-67 A-0032 Reflactive Index (n.sub.D.sup.20) 1.4819 A-0033 Melting Point ( C.) 117-118 A-0035 Reflactive Index (n.sub.D.sup.20) 1.5032 A-0036 Melting Point ( C.) 125-127 A-0037 Reflactive Index (n.sub.D.sup.20) 1.4810 A-0038 Melting Point ( C.) 77-80 A-0039 Reflactive Index (n.sub.D.sup.20) 1.5032 A-0040 Melting Point ( C.) 105-107 A-0043 Reflactive Index (n.sub.D.sup.20) 1.4809 A-0044 Melting Point ( C.) 68-70 A-0046 Reflactive Index (n.sub.D.sup.20) 1.5004 A-0047 Melting Point ( C.) 97-98 A-0051 Reflactive Index (n.sub.D.sup.20) 1.4769 A-0052 Melting Point ( C.) 78-79 A-0055 Reflactive Index (n.sub.D.sup.20) 1.4987 A-0056 Melting Point ( C.) 77-79 A-0061 Reflactive Index (n.sub.D.sup.20) 1.4900 A-0064 Reflactive Index (n.sub.D.sup.20) 1.4989 A-0065 Melting Point ( C.) 106-109 A-0066 Melting Point ( C.) 113-114

(150) TABLE-US-00044 TABLE 44 Compound No. Physical Property A-0068 Reflactive Index (n.sub.D.sup.20) 1.5011 A-0069 Melting Point ( C.) 138-139 A-0070 Reflactive Index (n.sub.D.sup.20) 1.4760 A-0071 Melting Point ( C.) 98-100 A-0074 Reflactive Index (n.sub.D.sup.20) 1.4748 A-0075 Melting Point ( C.) 74-75 A-0076 Reflactive Index (n.sub.D.sup.20) 1.4830 A-0077 Melting Point ( C.) 65-66 A-0078 Reflactive Index (n.sub.D.sup.20) 1.4961 A-0079 Melting Point ( C.) 81-83 A-0081 Reflactive Index (n.sub.D.sup.20) 1.4820 A-0085 Reflactive Index (n.sub.D.sup.20) 1.4780 A-0086 Melting Point ( C.) 84-85 A-0087 Reflactive Index (n.sub.D.sup.20) 1.4915 A-0088 Melting Point ( C.) 62-64 A-0089 Reflactive Index (n.sub.D.sup.20) 1.4933 A-0090 Melting Point ( C.) 83-84 A-0091 Reflactive Index (n.sub.D.sup.20) 1.4865 A-0092 Melting Point ( C.) 51-52 A-0094 Melting Point ( C.) 108-110 A-0108 Melting Point ( C.) 50-51 A-0109 Melting Point ( C.) 56-57 A-0110 Melting Point ( C.) 76-77 A-0111 Melting Point ( C.) 105-107 A-0112 Reflactive Index (n.sub.D.sup.20) 1.5032 A-0113 Melting Point ( C.) 74-75 A-0114 Melting Point ( C.) 76-77 A-0115 Reflactive Index (n.sub.D.sup.20) 1.5160 A-0116 Reflactive Index (n.sub.D.sup.20) 1.4834 A-0117 Melting Point ( C.) 52-54 A-0118 Reflactive Index (n.sub.D.sup.20) 1.4899 A-0119 Melting Point ( C.) 104-105 A-0120 Reflactive Index (n.sub.D.sup.20) 1.4790 A-0122 Reflactive Index (n.sub.D.sup.20) 1.4790 A-0123 Melting Point ( C.) 58-60 A-0125 Reflactive Index (n.sub.D.sup.20) 1.4949 A-0126 Melting Point ( C.) 46-48 A-0130 Melting Point ( C.) 59-60 A-0132 Reflactive Index (n.sub.D.sup.20) 1.4842

(151) TABLE-US-00045 TABLE 45 Compound No. Physical Property A-0133 Melting Point ( C.) 48-50 A-0141 Melting Point ( C.) 60-61 A-0143 Reflactive Index (n.sub.D.sup.20) 1.4871 A-0144 Melting Point ( C.) 47-48 A-0145 Melting Point ( C.) 78-81 A-0147 Reflactive Index (n.sub.D.sup.20) 1.4870 A-0157 Melting Point ( C.) 86-88 A-0159 Reflactive Index (n.sub.D.sup.20) 1.4542 A-0160 Melting Point ( C.) 100-103 A-0163 Reflactive Index (n.sub.D.sup.20) 1.4549 A-0164 Melting Point ( C.) 79-81 A-0167 Reflactive Index (n.sub.D.sup.20) 1.4562 A-0168 Melting Point ( C.) 33-35 A-0169 Reflactive Index (n.sub.D.sup.20) 1.4631 A-0170 Melting Point ( C.) 44-47 A-0172 Reflactive Index (n.sub.D.sup.20) 1.4303 A-0173 Melting Point ( C.) 72-74 A-0174 Reflactive Index (n.sub.D.sup.20) 1.4365 A-0175 Melting Point ( C.) 57-59 A-0180 Reflactive Index (n.sub.D.sup.20) 1.4429 A-0181 Melting Point ( C.) 94-96 A-0184 Reflactive Index (n.sub.D.sup.20) 1.4200 A-0185 Melting Point ( C.) 47-48 A-0186 Reflactive Index (n.sub.D.sup.20) 1.4184 A-0187 Melting Point ( C.) 56-58 A-0188 Reflactive Index (n.sub.D.sup.20) 1.4445 A-0199 Reflactive Index (n.sub.D.sup.20) 1.4554 A-0200 Reflactive Index (n.sub.D.sup.20) 1.4613 A-0203 Reflactive Index (n.sub.D.sup.20) 1.4562 A-0204 Reflactive Index (n.sub.D.sup.20) 1.4644 A-0205 Reflactive Index (n.sub.D.sup.20) 1.4678 A-0206 Melting Point ( C.) 39-42 A-0207 Reflactive Index (n.sub.D.sup.20) 1.4725 A-0208 Reflactive Index (n.sub.D.sup.20) 1.4802 A-0211 Reflactive Index (n.sub.D.sup.20) 1.419 A-0212 Reflactive Index (n.sub.D.sup.20) 1.4273 A-0213 Reflactive Index (n.sub.D.sup.20) 1.4382 A-0214 Reflactive Index (n.sub.D.sup.20) 1.4378 A-0215 Reflactive Index (n.sub.D.sup.20) 1.4309

(152) TABLE-US-00046 TABLE 46 Compound No. Physical Property A-0216 Reflactive Index (n.sub.D.sup.20) 1.4341 A-0217 Reflactive Index (n.sub.D.sup.20) 1.4341 A-0218 Reflactive Index (n.sub.D.sup.20) 1.4359 A-0219 Reflactive Index (n.sub.D.sup.20) 1.4200 A-0220 Reflactive Index (n.sub.D.sup.20) 1.4321 A-0221 Reflactive Index (n.sub.D.sup.20) 1.4368 A-0222 Reflactive Index (n.sub.D.sup.20) 1.4401 A-0223 Reflactive Index (n.sub.D.sup.20) 1.4328 A-0224 Melting Point ( C.) 45-47 A-0225 Reflactive Index (n.sub.D.sup.20) 1.4163 A-0226 Reflactive Index (n.sub.D.sup.20) 1.4115 A-0227 Reflactive Index (n.sub.D.sup.20) 1.3980 A-0228 Reflactive Index (n.sub.D.sup.20) 1.4079 A-0229 Reflactive Index (n.sub.D.sup.20) 1.4018 A-0230 Melting Point ( C.) 43-44 A-0232 Reflactive Index (n.sub.D.sup.20) 1.3759 A-0243 Reflactive Index (n.sub.D.sup.20) 1.4961 A-0244 Melting Point ( C.) 79-80 A-0249 Reflactive Index (n.sub.D.sup.20) 1.4947 A-0250 Reflactive Index (n.sub.D.sup.20) 1.4929 A-0253 Reflactive Index (n.sub.D.sup.20) 1.4751 A-0254 Melting Point ( C.) 116-118 A-0260 Reflactive Index (n.sub.D.sup.20) 1.4963 A-0261 Reflactive Index (n.sub.D.sup.20) 1.5132 A-0262 Melting Point ( C.) 89-92 A-0263 Reflactive Index (n.sub.D.sup.20) 1.5241 A-0264 Reflactive Index (n.sub.D.sup.20) 1.5102 A-0266 Reflactive Index (n.sub.D.sup.20) 1.5260 A-0269 Reflactive Index (n.sub.D.sup.20) 1.5092 A-0270 Melting Point ( C.) 53-55 A-0271 Reflactive Index (n.sub.D.sup.20) 1.5078 A-0273 Reflactive Index (n.sub.D.sup.20) 1.5211 A-0275 Reflactive Index (n.sub.D.sup.20) 1.5133 A-0277 Reflactive Index (n.sub.D.sup.20) 1.5195 A-0279 Reflactive Index (n.sub.D.sup.20) 1.5160 A-0281 Reflactive Index (n.sub.D.sup.20) 1.5071 A-0285 Reflactive Index (n.sub.D.sup.20) 1.4981 A-0287 Reflactive Index (n.sub.D.sup.20) 1.5206 A-0289 Reflactive Index (n.sub.D.sup.20) 1.4943

(153) TABLE-US-00047 TABLE 47 Compound No. Physical Property A-0290 Reflactive Index (n.sub.D.sup.20) 1.4940 A-0291 Reflactive Index (n.sub.D.sup.20) 1.5089 A-0294 Reflactive Index (n.sub.D.sup.20) 1.5199 A-0299 Reflactive Index (n.sub.D.sup.20) 1.5102 A-0301 Reflactive Index (n.sub.D.sup.20) 1.4960 A-0303 Reflactive Index (n.sub.D.sup.20) 1.5094 A-0307 Reflactive Index (n.sub.D.sup.20) 1.4761 A-0308 Melting Point ( C.) 54-56 A-0311 Reflactive Index (n.sub.D.sup.20) 1.4741 A-0313 Melting Point ( C.) 75-78 A-0314 Melting Point ( C.) 93-96 A-0315 Reflactive Index (n.sub.D.sup.20) 1.4912 A-0316 Melting Point ( C.) 85-88 A-0318 Melting Point ( C.) 77-80 A-0319 Reflactive Index (n.sub.D.sup.20) 1.4851 A-0320 Melting Point ( C.) 116-117 A-0321 Reflactive Index (n.sub.D.sup.20) 1.4969 A-0322 Melting Point ( C.) 117-118 A-0324 Reflactive Index (n.sub.D.sup.20) 1.4752 A-0325 Reflactive Index (n.sub.D.sup.20) 1.4832 A-0326 Melting Point ( C.) 119-122 A-0327 Melting Point ( C.) 92-95 A-0330 Melting Point ( C.) 115-118 A-0331 Melting Point ( C.) 120-121 A-0338 Reflactive Index (n.sub.D.sup.20) 1.4751 A-0339 Reflactive Index (n.sub.D.sup.20) 1.4798 A-0340 Reflactive Index (n.sub.D.sup.20) 1.4831 A-0341 Reflactive Index (n.sub.D.sup.20) 1.4859 A-0342 Reflactive Index (n.sub.D.sup.20) 1.4968 A-0343 Melting Point ( C.) 66-67 A-0346 Reflactive Index (n.sub.D.sup.20) 1.4950 A-0347 Melting Point ( C.) 89-90 A-0349 Reflactive Index (n.sub.D.sup.20) 1.5321 A-0350 Melting Point ( C.) 117-118 A-0352 Melting Point ( C.) 83-84 A-0353 Melting Point ( C.) 51-52 A-0354 Melting Point ( C.) 88-90 A-0356 Melting Point ( C.) 54-56 A-0359 Melting Point ( C.) 74-77

(154) TABLE-US-00048 TABLE 48 Compound No. Physical Property A-0360 Reflactive Index (n.sub.D.sup.20) 1.5079 A-0363 Reflactive Index (n.sub.D.sup.20) 1.5012 A-0364 Melting Point ( C.) 46-47 A-0365 Reflactive Index (n.sub.D.sup.20) 1.5104 A-0366 Melting Point ( C.) 42-43 A-0368 Melting Point ( C.) 69-71 A-0369 Reflactive Index (n.sub.D.sup.20) 1.5089 A-0374 Reflactive Index (n.sub.D.sup.20) 1.4990 A-0375 Melting Point ( C.) 48-50 A-0379 Reflactive Index (n.sub.D.sup.20) 1.5217 A-0387 Melting Point ( C.) 68-70 A-0388 Melting Point ( C.) 111-112 A-0391 Melting Point ( C.) 88-89 A-0392 Melting Point ( C.) 95-98 A-0393 Melting Point ( C.) 98-99 A-0394 Melting Point ( C.) 109-110 A-0395 Melting Point ( C.) 93-94 A-0396 Melting Point ( C.) 108-109 A-0405 Reflactive Index (n.sub.D.sup.20) 1.4741 A-0406 Reflactive Index (n.sub.D.sup.20) 1.4800 A-0415 Reflactive Index (n.sub.D.sup.20) 1.4762 A-0417 Reflactive Index (n.sub.D.sup.20) 1.4882 A-0418 Melting Point ( C.) 57-59 A-0422 Reflactive Index (n.sub.D.sup.20) 1.4855 A-0423 Reflactive Index (n.sub.D.sup.20) 1.4869 A-0431 Reflactive Index (n.sub.D.sup.20) 1.4742 A-0433 Reflactive Index (n.sub.D.sup.20) 1.4932 A-0434 Melting Point ( C.) 49-50 A-0435 Melting Point ( C.) 51-52 A-0437 Reflactive Index (n.sub.D.sup.20) 1.5000 A-0438 Reflactive Index (n.sub.D.sup.20) 1.4878 A-0439 Reflactive Index (n.sub.D.sup.20) 1.4889 A-0441 Melting Point ( C.) 68-69 A-0443 Melting Point ( C.) 41-42 A-0444 Reflactive Index (n.sub.D.sup.20) 1.5006 A-0445 Melting Point ( C.) 63-66 A-0446 Reflactive Index (n.sub.D.sup.20) 1.4947 A-0447 Reflactive Index (n.sub.D.sup.20) 1.4931 A-0448 Reflactive Index (n.sub.D.sup.20) 1.4781

(155) TABLE-US-00049 TABLE 49 Compound No. Physical Property A-0449 Melting Point ( C.) 69-70 A-0470 Reflactive Index (n.sub.D.sup.20) 1.4770 A-0471 Melting Point ( C.) 42-44 A-0472 Reflactive Index (n.sub.D.sup.20) 1.4905 A-0473 Melting Point ( C.) 43-46 A-0474 Reflactive Index (n.sub.D.sup.20) 1.4886 A-0475 Reflactive Index (n.sub.D.sup.20) 1.4862 A-0476 Reflactive Index (n.sub.D.sup.20) 1.4951 A-0477 Melting Point ( C.) 45-48 A-0478 Reflactive Index (n.sub.D.sup.20) 1.5059 A-0479 Melting Point ( C.) 43-45 A-0481 Reflactive Index (n.sub.D.sup.20) 1.4859 A-0482 Reflactive Index (n.sub.D.sup.20) 1.4960 A-0483 Reflactive Index (n.sub.D.sup.20) 1.491 A-0484 Reflactive Index (n.sub.D.sup.20) 1.4759 A-0485 Reflactive Index (n.sub.D.sup.20) 1.4800 A-0486 Reflactive Index (n.sub.D.sup.20) 1.5086 A-0487 Reflactive Index (n.sub.D.sup.20) 1.5102 A-0488 Reflactive Index (n.sub.D.sup.20) 1.5005 A-0489 Reflactive Index (n.sub.D.sup.20) 1.4978 A-0490 Reflactive Index (n.sub.D.sup.20) 1.5181 A-0495 Reflactive Index (n.sub.D.sup.20) 1.4839 A-0496 Reflactive Index (n.sub.D.sup.20) 1.4782 A-0502 Reflactive Index (n.sub.D.sup.20) 1.4813 A-0503 Reflactive Index (n.sub.D.sup.20) 1.4773 A-0504 Reflactive Index (n.sub.D.sup.20) 1.4814 A-0505 Melting Point ( C.) 48-49 A-0507 Reflactive Index (n.sub.D.sup.20) 1.4932 A-0508 Melting Point ( C.) 43-44 A-0510 Melting Point ( C.) 44-45 A-0524 Melting Point ( C.) 82-83 A-0525 Melting Point ( C.) 50-51 A-0526 Reflactive Index (n.sub.D.sup.20) 1.4920 A-0533 Melting Point ( C.) 80-81 A-0534 Melting Point ( C.) 92-93 A-0535 Reflactive Index (n.sub.D.sup.20) 1.4709 A-0536 Melting Point ( C.) 73-74 A-0539 Melting Point ( C.) 74-77 A-0543 Reflactive Index (n.sub.D.sup.20) 1.4949

(156) TABLE-US-00050 TABLE 50 Compound No. Physical Property A-0553 Reflactive Index (n.sub.D.sup.20) 1.4914 A-0555 Reflactive Index (n.sub.D.sup.20) 1.5025 A-0556 Melting Point ( C.) 40-42 A-0558 Reflactive Index (n.sub.D.sup.20) 1.5052 A-0559 Reflactive Index (n.sub.D.sup.20) 1.5125 A-0560 Melting Point ( C.) 49-50 A-0561 Reflactive Index (n.sub.D.sup.20) 1.5201 A-0562 Melting Point ( C.) 57-59 A-0563 Reflactive Index (n.sub.D.sup.20) 1.5025 A-0571 Reflactive Index (n.sub.D.sup.20) 1.4957 A-0572 Reflactive Index (n.sub.D.sup.20) 1.5000 A-0573 Reflactive Index (n.sub.D.sup.20) 1.5023 A-0574 Reflactive Index (n.sub.D.sup.20) 1.4982 A-0575 Reflactive Index (n.sub.D.sup.20) 1.5098 A-0576 Reflactive Index (n.sub.D.sup.20) 1.5087 A-0577 Melting Point ( C.) 68-69 A-0578 Melting Point ( C.) 58-59 A-0587 Reflactive Index (n.sub.D.sup.20) 1.4941 A-0588 Reflactive Index (n.sub.D.sup.20) 1.4981 A-0589 Reflactive Index (n.sub.D.sup.20) 1.5010 A-0590 Melting Point ( C.) 41-42 A-0591 Melting Point ( C.) 50-51 A-0592 Reflactive Index (n.sub.D.sup.20) 1.5000 A-0594 Melting Point ( C.) 112-113 A-0599 Melting Point ( C.) 65-67 A-0605 Melting Point ( C.) 87-90 A-0606 Melting Point ( C.) 78-81 A-0610 Reflactive Index (n.sub.D.sup.20) 1.4909 A-0611 Melting Point ( C.) 96-99 A-0615 Melting Point ( C.) 60-61 A-0616 Melting Point CO 58-60 A-0617 Melting Point ( C.) 38-41 A-0618 Melting Point ( C.) 82-83 A-0622 Reflactive Index (n.sub.D.sup.20) 1.4864 A-0623 Melting Point ( C.) 86-88 A-0625 Reflactive Index (n.sub.D.sup.20) 1.4861 A-0626 Reflactive Index (n.sub.D.sup.20) 1.4899 A-0631 Reflactive Index (n.sub.D.sup.20) 1.4845 A-0632 Melting Point ( C.) 72-74

(157) TABLE-US-00051 TABLE 51 Compound No. Physical Property A-0638 Melting Point ( C.) 39-41 A-0640 Reflactive Index (n.sub.D.sup.20) 1.4902 A-0641 Melting Point ( C.) 68-69 A-0642 Melting Point ( C.) 43-44 A-0643 Melting Point ( C.) 61-63 A-0644 Reflactive Index (n.sub.D.sup.20) 1.5000 A-0662 Reflactive Index (n.sub.D.sup.20) 1.5353 A-0663 Reflactive Index (n.sub.D.sup.20) 1.5190 A-0665 Reflactive Index (n.sub.D.sup.20) 1.5309 A-0666 Reflactive Index (n.sub.D.sup.20) 1.5272 A-0667 Reflactive Index (n.sub.D.sup.20) 1.5509 A-0668 Reflactive Index (n.sub.D.sup.20) 1.5155 A-0670 Reflactive Index (n.sub.D.sup.20) 1.5281 A-0671 Reflactive Index (n.sub.D.sup.20) 1.5325 A-0672 Reflactive Index (n.sub.D.sup.20) 1.5299 A-0673 Reflactive Index (n.sub.D.sup.20) 1.5161 A-0674 Reflactive Index (n.sub.D.sup.20) 1.5130 A-0675 Reflactive Index (n.sub.D.sup.20) 1.5122 A-0676 Reflactive Index (n.sub.D.sup.20) 1.5210 A-0677 Reflactive Index (n.sub.D.sup.20) 1.5240 A-0680 Reflactive Index (n.sub.D.sup.20) 1.5085 A-0682 Reflactive Index (n.sub.D.sup.20) 1.5121 A-0683 Reflactive Index (n.sub.D.sup.20) 1.4769 A-0684 Reflactive Index (n.sub.D.sup.20) 1.5361 A-0686 Melting Point ( C.) 108-110 A-0688 Melting Point ( C.) 111-112 A-0690 Reflactive Index (n.sub.D.sup.20) 1.5016 A-0692 Melting Point ( C.) 81-83 A-0693 Reflactive Index (n.sub.D.sup.20) 1.5092 A-0694 Melting Point ( C.) 86-87 A-0695 Melting Point ( C.) 39-41 A-0696 Melting Point ( C.) 125-127 A-0697 Melting Point ( C.) 102-104 A-0698 Melting Point ( C.) 113-116 A-0699 Melting Point ( C.) 53-55 A-0700 Melting Point ( C.) 112-114 A-0703 Melting Point ( C.) 63-64 A-0709 Melting Point ( C.) 59-60 A-0710 Melting Point ( C.) 98-100

(158) TABLE-US-00052 TABLE 52 Compound No. Physical Property A-0711 Melting Point ( C.) 61-63 A-0712 Melting Point ( C.) 89-90 A-0713 Reflactive Index (n.sub.D.sup.20) 1.5188 A-0716 Melting Point ( C.) 66-68 A-0717 Melting Point ( C.) 80-81 A-0718 Melting Point ( C.) 79-82 A-0720 Reflactive Index (n.sub.D.sup.20) 1.5330 A-0721 Melting Point ( C.) 128-129 A-0722 Melting Point ( C.) 50-51 A-0723 Melting Point ( C.) 90-91 A-0724 Melting Point ( C.) 96-97 A-0725 Melting Point ( C.) 144-145 A-0726 Melting Point ( C.) 117-119 A-0727 Melting Point ( C.) 93-96 A-0728 Melting Point ( C.) 47-48.5 A-0729 Melting Point ( C.) 117-118 A-0730 Melting Point ( C.) 70-71 A-0731 Melting Point ( C.) 125-126 A-0732 Reflactive Index (n.sub.D.sup.20) 1.5021 A-0733 Melting Point ( C.) 144-145 A-0734 Reflactive Index (n.sub.D.sup.20) 1.5072 A-0735 Melting Point ( C.) 132-134 A-0736 Melting Point ( C.) 122-123 A-0739 Melting Point ( C.) 79-80 A-0740 Melting Point ( C.) 138-140 A-0741 Melting Point ( C.) 52-53 A-0742 Melting Point ( C.) 114-116 A-0743 Melting Point ( C.) 52-53 A-0744 Melting Point ( C.) 103-104 A-0746 Melting Point ( C.) 101-102 A-0748 Reflactive Index (n.sub.D.sup.20) 1.4766 A-0749 Melting Point ( C.) 96-98 A-0750 Melting Point ( C.) 85-87 A-0751 Reflactive Index (n.sub.D.sup.20) 1.5319 A-0752 Melting Point ( C.) 78-80 A-0753 Reflactive Index (n.sub.D.sup.20) 1.5224 A-0754 Melting Point ( C.) 92-94 A-0755 Reflactive Index (n.sub.D.sup.20) 1.5279 A-0756 Melting Point ( C.) 102-103

(159) TABLE-US-00053 TABLE 53 Compound No. Physical Property A-0757 Reflactive Index(n.sub.D.sup.20) 1.5500 A-0758 Melting Point ( C.) 104-105 A-0759 Reflactive Index (n.sub.D.sup.20) 1.5030 A-0760 Melting Point ( C.) 125-128 A-0761 Reflactive Index (n.sub.D.sup.20) 1.4979 A-0762 Reflactive Index (n.sub.D.sup.20) 1.5050 A-0763 Reflactive Index (n.sub.D.sup.20) 1.4991 A-0764 Melting Point ( C.) 95-96 A-0765 Reflactive Index (n.sub.D.sup.20) 1.5085 A-0766 Melting Point ( C.) 91-92 A-0767 Melting Point ( C.) 109-110 A-0768 Melting Point ( C.) 91-92 A-0769 Melting Point ( C.) 115-116 A-0771 Melting Point ( C.) 115-116 A-0772 Reflactive Index (n.sub.D.sup.20) 1.5190 A-0773 Melting Point ( C.) 89-90 A-0774 Melting Point ( C.) 75-76 A-0775 Melting Point ( C.) 81-82 A-0776 Melting Point ( C.) 118-120 A-0777 Melting Point ( C.) 40-41 A-0778 Reflactive Index (n.sub.D.sup.20) 1.4976 A-0779 Melting Point ( C.) 81-84 A-0780 Reflactive Index (n.sub.D.sup.20) 1.5009 A-0781 Melting Point ( C.) 94-95 A-0782 Melting Point ( C.) 111-112 A-0783 Melting Point ( C.) 80-81 A-0784 Melting Point ( C.) 120-122 A-0786 Reflactive Index (n.sub.D.sup.20) 1.5158 A-0787 Reflactive Index (n.sub.D.sup.20) 1.5247 A-0788 Melting Point ( C.) 89-90 A-0789 Melting Point ( C.) 114-115 A-0790 Melting Point ( C.) 51-54 A-0791 Melting Point ( C.) 131-134 A-0792 Melting Point ( C.) 110-111 A-0793 Melting Point ( C.) 126-127 A-0795 Melting Point ( C.) 117-118 A-0796 Melting Point ( C.) 133-136 A-0797 Reflactive Index (n.sub.D.sup.20) 1.5062 A-0798 Reflactive Index (n.sub.D.sup.20) 1.4980

(160) TABLE-US-00054 TABLE 54 Compound No. Physical Property A-0799 Melting Point ( C.) 79-81 A-0800 Melting Point ( C.) 83-84 A-0801 Melting Point ( C.) 109-110 A-0802 Reflactive Index (n.sub.D.sup.20) 1.5540 A-0803 Melting Point ( C.) 135-136 A-0805 Melting Point ( C.) 92-93 A-0806 Melting Point ( C.) 101-102 A-0807 Melting Point ( C.) 115-116 A-0808 Melting Point ( C.) 106-109 A-0809 Reflactive Index (n.sub.D.sup.20) 1.5051 A-0810 Melting Point ( C.) 88-90 A-0811 Reflactive Index (n.sub.D.sup.20) 1.5021 A-0812 Melting Point ( C.) 107-109 A-0813 Reflactive Index (n.sub.D.sup.20) 1.4896 A-0814 Melting Point ( C.) 104-106 A-0815 Reflactive Index (n.sub.D.sup.20) 1.4987 A-0816 Melting Point ( C.) 111-112 A-0817 Melting Point ( C.) 98-100 A-0818 Melting Point ( C.) 86-88 A-0819 Reflactive Index (n.sub.D.sup.20) 1.5210 A-0820 Melting Point ( C.) 99-100 A-0821 Melting Point ( C.) 90-91 A-0823 Melting Point ( C.) 93-95 A-0824 Reflactive Index (n.sub.D.sup.20) 1.5005 A-0825 Melting Point ( C.) 72-73 A-0826 Reflactive Index (n.sub.D.sup.20) 1.5282 A-0827 Melting Point ( C.) 76-78 A-0828 Reflactive Index (n.sub.D.sup.20) 1.5463 A-0829 Melting Point ( C.) 144-145 A-0830 Reflactive Index (n.sub.D.sup.20) 1.5589 A-0831 Reflactive Index (n.sub.D.sup.20) 1.5479 A-0832 Reflactive Index (n.sub.D.sup.20) 1.5406 A-0833 Melting Point ( C.) 49-52 A-0837 Melting Point ( C.) 96-97 A-0838 Reflactive Index (n.sub.D.sup.20) 1.4970 A-0839 Melting Point ( C.) 101-102 A-0844 Reflactive Index (n.sub.D.sup.20) 1.4962 A-0845 Reflactive Index (n.sub.D.sup.20) 1.5025 A-0846 Reflactive Index (n.sub.D.sup.20) 1.5270

(161) TABLE-US-00055 TABLE 55 Compound No. Physical Property A-0847 Melting Point ( C.) 58-60 A-0848 Reflactive Index (n.sub.D.sup.20) 1.5382 A-0849 Melting Point ( C.) 92-94 A-0853 Reflactive Index (n.sub.D.sup.20) 1.5140 A-0854 Melting Point ( C.) 100-103 A-0855 Reflactive Index (n.sub.D.sup.20) 1.5028 A-0856 Melting Point ( C.) 98-100 A-0857 Reflactive Index (n.sub.D.sup.20) 1.4969 A-0858 Melting Point ( C.) 101-102 A-0860 Reflactive Index (n.sub.D.sup.20) 1.5256 A-0864 Melting Point ( C.) 87-88 A-0869 Reflactive Index (n.sub.D.sup.20) 1.5241 A-0870 Reflactive Index (n.sub.D.sup.20) 1.5207 A-0876 Melting Point ( C.) 82-84 A-0877 Reflactive Index (n.sub.D.sup.20) 1.5442 A-0878 Melting Point ( C.) 44-46 A-0880 Reflactive Index (n.sub.D.sup.20) 1.5235 A-0881 Melting Point ( C.) 69-72 A-0884 Reflactive Index (n.sub.D.sup.20) 1.5201 A-0885 Melting Point ( C.) 49-50 A-0888 Reflactive Index (n.sub.D.sup.20) 1.5602 A-0902 Reflactive Index (n.sub.D.sup.20) 1.5450 A-0903 Melting Point ( C.) 83-85 A-0906 Melting Point ( C.) 140-143 A-0907 Reflactive Index (n.sub.D.sup.20) 1.5382 A-0908 Reflactive Index (n.sub.D.sup.20) 1.5508 A-0909 Melting Point ( C.) 103-105 A-0913 Reflactive Index (n.sub.D.sup.20) 1.5486 A-0914 Reflactive Index (n.sub.D.sup.20) 1.5580 A-0915 Reflactive Index (n.sub.D.sup.20) 1.5679 A-0916 Reflactive Index (n.sub.D.sup.20) 1.5649 A-0917 Reflactive Index (n.sub.D.sup.20) 1.5578 A-0918 Reflactive Index (n.sub.D.sup.20) 1.5500 A-0919 Reflactive Index (n.sub.D.sup.20) 1.5552 A-0920 Reflactive Index (n.sub.D.sup.20) 1.5539 A-0921 Reflactive Index (n.sub.D.sup.20) 1.5549 A-0922 Melting Point ( C.) 75-77 A-0923 Reflactive Index (n.sub.D.sup.20) 1.5171 A-0924 Melting Point ( C.) 83-86

(162) TABLE-US-00056 TABLE 56 Compound No. Physical Property A-0925 Melting Point ( C.) 75-76 A-0926 Reflactive Index (n.sub.D.sup.20) 1.5667 A-0927 Melting Point ( C.) 75-76 A-0933 Reflactive Index(n.sub.D.sup.20) 1.5471 A-0936 Reflactive Index (n.sub.D.sup.20) 1.5411 A-0940 Melting Point ( C.) 71-72 A-0941 Reflactive Index (n.sub.D.sup.20) 1.5259 A-0942 Melting Point ( C.) 112-114 A-0943 Melting Point ( C.) 93-96 A-0948 Melting Point ( C.) 57-58 A-0950 Melting Point ( C.) 136-138 A-0956 Reflactive Index (n.sub.D.sup.20) 1.5046 A-0957 Melting Point ( C.) 94-95 A-0958 Melting Point ( C.) 49-50 A-0959 Reflactive Index (n.sub.D.sup.20) 1.4908 A-0960 Melting Point ( C.) 91-92 A-0963 Reflactive Index (n.sub.D.sup.20) 1.5309 A-0964 Reflactive Index (n.sub.D.sup.20) 1.5341 A-0965 Reflactive Index (n.sub.D.sup.20) 1.5219 A-0966 Reflactive Index (n.sub.D.sup.20) 1.5269 A-0968 Reflactive Index (n.sub.D.sup.20) 1.5635 A-0969 Melting Point ( C.) 93-94 A-0972 Reflactive Index (n.sub.D.sup.20) 1.4600 A-0973 Melting Point ( C.) 71-74 A-0975 Reflactive Index (n.sub.D.sup.20) 1.5613 A-0976 Melting Point ( C.) 50-51 A-0977 Reflactive Index (n.sub.D.sup.20) 1.4741 A-0978 Melting Point ( C.) 85-87 A-0979 Reflactive Index (n.sub.D.sup.20) 1.5143 A-0980 Melting Point ( C.) 76-77 A-0981 Reflactive Index (n.sub.D.sup.20) 1.4626 A-0982 Melting Point ( C.) 50-53 A-0983 Reflactive Index (n.sub.D.sup.20) 1.5621 A-0984 Reflactive Index (n.sub.D.sup.20) 1.4711 A-0985 Melting Point ( C.) 66-69 A-0988 Melting Point ( C.) 76-77 A-0989 Reflactive Index (n.sub.D.sup.20) 1.5024 A-0990 Melting Point ( C.) 62-63 A-0991 Reflactive Index (n.sub.D.sup.20) 1.4639

(163) TABLE-US-00057 TABLE 57 Compound No. Physical Property A-0992 Melting Point ( C.) 35-37 A-0996 Melting Point ( C.) 48-51 A-0997 Melting Point ( C.) 55-58 A-0999 Melting Point ( C.) 87-88 A-1000 Melting Point ( C.) 104-105 A-1001 Melting Point ( C.) 91-92 A-1002 Melting Point ( C.) 70-73 A-1003 Reflactive Index (n.sub.D.sup.20) 1.5103 A-1004 Reflactive Index (n.sub.D.sup.20) 1.5094 A-1005 Melting Point ( C.) 86-88 A-1006 Melting Point ( C.) 72-75 A-1007 Reflactive Index (n.sub.D.sup.20) 1.5254 A-1008 Melting Point ( C.) 87-88 A-1009 Reflactive Index (n.sub.D.sup.20) 1.5101 A-1010 Melting Point ( C.) 78-80 A-1011 Reflactive Index (n.sub.D.sup.20) 1.5272 A-1012 Melting Point ( C.) 91-92 A-1015 Reflactive Index (n.sub.D.sup.20) 1.5226 A-1016 Melting Point ( C.) 92-94 A-1020 Reflactive Index (n.sub.D.sup.20) 1.4900 A-1021 Melting Point ( C.) 105-108 A-1024 Reflactive Index (n.sub.D.sup.20) 1.4931 A-1025 Reflactive Index (n.sub.D.sup.20) 1.4852 A-1026 Melting Point ( C.) 71-72 A-1027 Reflactive Index (n.sub.D.sup.20) 1.5430 A-1033 Reflactive Index (n.sub.D.sup.20) 1.4935 A-1037 Reflactive Index (n.sub.D.sup.20) 1.4792 A-1042 Reflactive Index (n.sub.D.sup.20) 1.4862 A-1048 Melting Point ( C.) 60-61 A-1050 Reflactive Index (n.sub.D.sup.20) 1.4850 A-1051 Reflactive Index (n.sub.D.sup.20) 1.4780 A-1052 Reflactive Index (n.sub.D.sup.20) 1.4802 A-1057 Reflactive Index (n.sub.D.sup.20) 1.4790 A-1058 Reflactive Index (n.sub.D.sup.20) 1.4859 A-1059 Melting Point ( C.) 63-64 A-1060 Melting Point ( C.) 75-76 A-1061 Reflactive Index (n.sub.D.sup.20) 1.4909 A-1062 Reflactive Index (n.sub.D.sup.20) 1.4942 A-1073 Melting Point ( C.) 67-70

(164) TABLE-US-00058 TABLE 58 Compound No. Physical Property A-1074 Reflactive Index (n.sub.D.sup.20) 1.4919 A-1075 Melting Point ( C.) 82-83 A-1079 Melting Point ( C.) 81-83 A-1080 Melting Point ( C.) 119-122 A-1081 Melting Point ( C.) 101-102 A-1082 Melting Point ( C.) 144-147 A-1087 Reflactive Index (n.sub.D.sup.20) 1.4991 A-1088 Melting Point ( C.) 89-92 A-1093 Reflactive Index (n.sub.D.sup.20) 1.5029 A-1094 Melting Point ( C.) 99-102 A-1097 Reflactive Index (n.sub.D.sup.20) 1.523 A-1098 Melting Point ( C.) 115-117 A-1099 Reflactive Index (n.sub.D.sup.20) 1.4985 A-1100 Reflactive Index (n.sub.D.sup.20) 1.5051 A-1102 Reflactive Index (n.sub.D.sup.20) 1.5152 A-1107 Melting Point ( C.) 92-93 A-1108 Melting Point ( C.) 142-143 A-1112 Reflactive Index (n.sub.D.sup.20) 1.4958 A-1113 Melting Point ( C.) 109-111 A-1117 Melting Point ( C.) 94-96 A-1119 Melting Point ( C.) 135-136 A-1122 Melting Point ( C.) 110-113 A-1123 Melting Point ( C.) 117-118 A-1125 Reflactive Index (n.sub.D.sup.20) 1.4881 A-1126 Melting Point ( C.) 70-72 A-1127 Reflactive Index (n.sub.D.sup.20) 1.5111 A-1128 Reflactive Index (n.sub.D.sup.20) 1.5049 A-1131 Melting Point ( C.) 70-73 A-1132 Melting Point ( C.) 70-73 A-1136 Reflactive Index (n.sub.D.sup.20) 1.4550 A-1137 Melting Point ( C.) 87-90 A-1138 Reflactive Index (n.sub.D.sup.20) 1.4826 A-1139 Melting Point ( C.) 98-101 A-1140 Reflactive Index (n.sub.D.sup.20) 1.4622 A-1141 Reflactive Index (n.sub.D.sup.20) 1.4682 A-1142 Reflactive Index (n.sub.D.sup.20) 1.4750 A-1143 Melting Point ( C.) 85-87 A-1150 Melting Point ( C.) 116-117 A-1151 Melting Point ( C.) 51-52

(165) TABLE-US-00059 TABLE 59 Compound No. Physical Property A-1152 Melting Point ( C.) 105-106 A-1153 Melting Point ( C.) 147-148 A-1154 Melting Point ( C.) 89-92 A-1155 Melting Point ( C.) 92-93 A-1157 Melting Point ( C.) 77-80 A-1158 Reflactive Index (n.sub.D.sup.20) 1.4679 A-1159 Reflactive Index (n.sub.D.sup.20) 1.4715 A-1164 Melting Point ( C.) 62-63 A-1165 Melting Point ( C.) 65-67 A-1166 Reflactive Index (n.sub.D.sup.20) 1.4919 A-1167 Melting Point ( C.) 67-68 A-1171 Reflactive Index (n.sub.D.sup.20) 1.5335 A-1172 Melting Point ( C.) 99-100 A-1174 Melting Point ( C.) 103-106 A-1175 Reflactive Index (n.sub.D.sup.20) 1.4721 A-1177 Reflactive Index (n.sub.D.sup.20) 1.4755 A-1178 Melting Point ( C.) 84-87 A-1180 Reflactive Index (n.sub.D.sup.20) 1.4729 A-1181 Reflactive Index (n.sub.D.sup.20) 1.4730 A-1183 Melting Point ( C.) 79-82 A-1185 Reflactive Index (n.sub.D.sup.20) 1.4685 A-1186 Melting Point ( C.) 107-108 A-1187 Melting Point ( C.) 105-107 A-1188 Melting Point ( C.) 84-85 A-1190 Reflactive Index (n.sub.D.sup.20) 1.4729 A-1191 Melting Point ( C.) 104-106 A-1192 Melting Point ( C.) 80-81 A-1195 Reflactive Index (n.sub.D.sup.20) 1.4720 A-1196 Melting Point ( C.) 90-91 A-1197 Reflactive Index (n.sub.D.sup.20) 1.4812 A-1200 Melting Point ( C.) 102-104 A-1202 Melting Point ( C.) 58-61 A-1203 Melting Point ( C.) 89-90 A-1205 Reflactive Index (n.sub.D.sup.20) 1.4801 A-1206 Reflactive Index (n.sub.D.sup.20) 1.4899 A-1207 Melting Point ( C.) 67-70 A-1209 Reflactive Index (n.sub.D.sup.20) 1.4925 A-1210 Reflactive Index (n.sub.D.sup.20) 1.4804 A-1211 Melting Point ( C.) 71-72

(166) TABLE-US-00060 TABLE 60 Compound No. Physical Property A-1212 Reflactive Index (n.sub.D.sup.20) 1.4880 A-1213 Melting Point ( C.) 46-48 A-1214 Melting Point ( C.) 99-100 A-1215 Reflactive Index (n.sub.D.sup.20) 1.5418 A-1216 Reflactive Index (n.sub.D.sup.20) 1.5391 A-1217 Melting Point ( C.) 69-70 A-1218 Melting Point ( C.) 80-82

(167) TABLE-US-00061 TABLE 61 Compound No. Physical Property B-0001 Reflactive Index (n.sub.D.sup.20) 1.4980 B-0002 Melting Point ( C.) 116-117 B-0003 Reflactive Index (n.sub.D.sup.20) 1.4599 B-0004 Reflactive Index (n.sub.D.sup.20) 1.4638 B-0005 Reflactive Index (n.sub.D.sup.20) 1.4830 B-0006 Reflactive Index (n.sub.D.sup.20) 1.4896 B-0007 Reflactive Index (n.sub.D.sup.20) 1.4839 B-0008 Reflactive Index (n.sub.D.sup.20) 1.4885 B-0009 Reflactive Index (n.sub.D.sup.20) 1.4880 B-0010 Reflactive Index (n.sub.D.sup.20) 1.4928 B-0011 Melting Point ( C.) 75-76 B-0012 Reflactive Index (n.sub.D.sup.20) 1.5291 B-0013 Melting Point ( C.) 102-103 B-0014 Reflactive Index (n.sub.D.sup.20) 1.5534 B-0015 Melting Point ( C.) 103-106 B-0016 Reflactive Index (n.sub.D.sup.20) 1.5528 B-0017 Reflactive Index (n.sub.D.sup.20) 1.5019 B-0018 Melting Point ( C.) 64-65 B-0019 Melting Point ( C.) 67-68 B-0020 Reflactive Index (n.sub.D.sup.20) 1.4952 B-0021 Melting Point ( C.) 124-126 B-0022 Reflactive Index (n.sub.D.sup.20) 1.4835 B-0023 Melting Point ( C.) 88-89 B-0024 Reflactive Index (n.sub.D.sup.20) 1.5051 B-0025 Melting Point ( C.) 85-86 B-0026 Melting Point ( C.) 57-59 B-0027 Melting Point ( C.) 53-54 B-0029 Reflactive Index (n.sub.D.sup.20) 1.5390 B-0030 Melting Point ( C.) 88-91 B-0032 Melting Point ( C.) 117-118 B-0033 Melting Point ( C.) 90-92 B-0034 Melting Point ( C.) 104-107 B-0035 Reflactive Index (n.sub.D.sup.20) 1.5013 B-0036 Reflactive Index (n.sub.D.sup.20) 1.5145 B-0037 Melting Point ( C.) 94-96 B-0038 Reflactive Index (n.sub.D.sup.20) 1.5028 B-0039 Melting Point ( C.) 73-74 B-0040 Melting Point ( C.) 93-95 B-0041 Melting Point ( C.) 85-87

(168) TABLE-US-00062 TABLE 62 Compound No. Physical Property B-0042 Reflactive Index (n.sub.D.sup.20) 1.5040 B-0043 Reflactive Index (n.sub.D.sup.20) 1.5220 B-0044 Melting Point ( C.) 87-89 B-0045 Reflactive Index (n.sub.D.sup.20) 1.5168 B-0046 Melting Point ( C.) 114-115 B-0047 Melting Point ( C.) 130-133 B-0048 Melting Point ( C.) 54-56 B-0049 Melting Point ( C.) 124-125 B-0050 Melting Point ( C.) 133-134 B-0051 Reflactive Index (n.sub.D.sup.20) 1.4976 B-0052 Melting Point ( C.) 147-149 B-0053 Melting Point ( C.) 54-55 B-0054 Melting Point ( C.) 117-118 B-0055 Reflactive Index (n.sub.D.sup.20) 1.5098 B-0056 Melting Point ( C.) 74-75 B-0058 Melting Point ( C.) 94-96 B-0059 Melting Point ( C.) 74-77 B-0061 Melting Point ( C.) 108-109 B-0062 Melting Point ( C.) 99-101 B-0064 Reflactive Index (n.sub.D.sup.20) 1.5210 B-0065 Melting Point ( C.) 142-144 B-0066 Reflactive Index (n.sub.D.sup.20) 1.5059 B-0067 Melting Point ( C.) 94-96 B-0068 Reflactive Index (n.sub.D.sup.20) 1.5085 B-0069 Melting Point ( C.) 126-127 B-0070 Reflactive Index (n.sub.D.sup.20) 1.4985 B-0071 Melting Point ( C.) 109-110 B-0072 Reflactive Index (n.sub.D.sup.20) 1.5031 B-0073 Melting Point ( C.) 78-79 B-0074 Reflactive Index (n.sub.D.sup.20) 1.4950 B-0075 Melting Point ( C.) 104-105 B-0076 Reflactive Index (n.sub.D.sup.20) 1.4970 B-0077 Melting Point ( C.) 77-78 B-0078 Reflactive Index (n.sub.D.sup.20) 1.4955 B-0079 Melting Point ( C.) 83-85 B-0080 Reflactive Index (n.sub.D.sup.20) 1.5051 B-0081 Melting Point ( C.) 68-69 B-0082 Reflactive Index (n.sub.D.sup.20) 1.4904 B-0083 Melting Point ( C.) 69-70

(169) TABLE-US-00063 TABLE 63 Compound No. Physical Property B-0084 Reflactive Index (n.sub.D.sup.20) 1.4713 B-0085 Melting Point ( C.) 92-94 B-0086 Reflactive Index (n.sub.D.sup.20) 1.4638 B-0087 Melting Point ( C.) 98-100 B-0088 Reflactive Index (n.sub.D.sup.20) 1.4912 B-0089 Melting Point ( C.) 115-117 B-0090 Reflactive Index (n.sub.D.sup.20) 1.5022 B-0091 Melting Point ( C.) 106-108 B-0092 Reflactive Index (n.sub.D.sup.20) 1.5005 B-0093 Reflactive Index (n.sub.D.sup.20) 1.4921 B-0094 Reflactive Index (n.sub.D.sup.20) 1.5022 B-0095 Melting Point ( C.) 106-108 B-0096 Melting Point ( C.) 57-58 B-0097 Reflactive Index (n.sub.D.sup.20) 1.5038 B-0098 Melting Point ( C.) 63-65 B-0099 Reflactive Index (n.sub.D.sup.20) 1.5042 B-0100 Melting Point ( C.) 110-111 B-0101 Reflactive Index (n.sub.D.sup.20) 1.5440 B-0102 Reflactive Index (n.sub.D.sup.20) 1.5120 B-0103 Melting Point ( C.) 117-118 B-0104 Reflactive Index (n.sub.D.sup.20) 1.5057 B-0105 Melting Point ( C.) 104-106 B-0106 Reflactive Index (n.sub.D.sup.20) 1.5441 B-0107 Reflactive Index (n.sub.D.sup.20) 1.5428 B-0108 Reflactive Index (n.sub.D.sup.20) 1.4988 B-0109 Reflactive Index (n.sub.D.sup.20) 1.5384 B-0113 Reflactive Index (n.sub.D.sup.20) 1.5578 B-0114 Melting Point ( C.) 89-100 B-0115 Melting Point ( C.) 86-89 B-0116 Melting Point ( C.) 114-115 B-0117 Melting Point ( C.) 84-85

(170) TABLE-US-00064 TABLE 64 Compound No. Physical Property C-0001 Reflactive Index (n.sub.D.sup.20) 1.4915 C-0002 Melting Point ( C.) 174-177 C-0003 Reflactive Index (n.sub.D.sup.20) 1.5185 C-0004 Melting Point ( C.) 145-146 C-0007 Reflactive Index (n.sub.D.sup.20) 1.529 C-0008 Melting Point ( C.) 167-169 C-0009 Reflactive Index (n.sub.D.sup.20) 1.5245 C-0010 Melting Point ( C.) 173-174 C-0011 Melting Point ( C.) 117-120 C-0013 Reflactive Index (n.sub.D.sup.20) 1.4918 C-0014 Reflactive Index (n.sub.D.sup.20) 1.5275 C-0016 Melting Point ( C.) 149-150

(171) TABLE-US-00065 TABLE 65 Physical Property Compound No. (.sup.1H-NMR DATA, in CDCl.sub.3/TMS (ppm)) A-0231 400 MHz 2.48(3H, s), 3.32(2H, q), 6.11(1H, d), 7.08 (1H, d), 7.43(1H, d) A-0234 400 MHz 3.37-3.47(1H, m), 3.70-3.81(1H, m), 6.16 (1H, d), 7.38(1H, d), 7.94(1H, d) A-0256 300 MHz 1.70-1.91(4H, m), 2.27-2.46(5H, m), 3.29 (2H, q), 4.03(2H, t), 6.96(1H, d), 7.13 (1H, d) A-0257 300 MHz 1.71-1.94(4H, m), 2.30-2.46(5H, m), 3.29- 3.50(2H, m), 4.12(2H, t), 6.99(1H, d), 7.54(1H, d) A-0259 300 MHz 2.37(3H, s), 3.30-3.51(2H, m), 5.30(1H, dd), 5.59(1H, dd), 6.19-6.51(1H, m), 7.11 (1H, d), 7.77(1H, d) A-0267 400 MHz 1.96-2.15(4H, m), 3.45(2H, q), 3.52(2H, t), 4.06(2H, t), 7.14(1H, s), 7.46(1H, s) A-0283 400 MHz 1.50-1.60(4H, m), 1.81-1.93(4H, m), 3.39- 3.49(4H, m), 4.02(2H, t), 7.13(1H, s), 7.45(1H, s) A-0284 300 MHz 1.53(4H, m), 1.70-2.03(4H, m), 2.17(3H, s), 2.38(3H, s), 3.26-3.43(4H, m), 3.94 (2H, t), 6.96(1H, s), 6.99(1H, s) A-0292 300 MHz 2.49(3H, s), 3.29(2H, q), 3.97(2H, t), 4.13(2H, t), 6.98(1H, d), 7.49(1H, d) A-0317 300 MHz 1.54-1.81(8H, m), 2.07-2.10(2H, m), 2.41 (3H, s), 3.30(2H, q), 3.94(2H, d), 6.96 (1H, d), 7.16(1H, d) A-0328 400 MHz 1.23-1.40(2H, m), 1.61-1.90(7H, m), 2.04- 2.16(2H, m), 2.41(3H, s), 3.29(2H, q), 4.05(2H, t), 6.97(1H, d), 7.15(1H, d) A-0329 400 MHz 1.23-1.51(2H, m), 1.60-1.88(7H, m), 2.03- 2.16(2H, m), 3.41(2H, q), 4.06(2H, t), 7.21(1H, d), 7.23(1H, d) A-0410 300 MHz 2.16-2.25(5H, m), 2.39(3H, s), 3.11(2H, t), 3.31(2H, q), 4.05(2H, t), 6.97(1H, s), 7.01(1H, s)

(172) TABLE-US-00066 TABLE 66 Physical Property Compound No. (.sup.1H-NMR DATA, in CDCl.sub.3/TMS (ppm)) A-0411 300 MHz 2.22-2.31(8H, m), 3.12(2H, t), 3.27-3.50(2H, m), 4.16(2H, m), 7.03(1H, s), 7.38(1H, s) A-0412 300 MHz 2.21-2.29(2H, m), 3.15(2H, t), 3.45(2H, q), 4.11(2H, t), 7.15(1H, s), 7.47(1H, s) A-0413 400 MHz 2.28(2H, quint), 3.15(2H, t), 3.32-3.44(1H, m), 3.69-3.81(1H, m), 4.25(2H, t), 7.48(1H, s), 7.50(1H, s) A-0416 300 MHz 1.90-2.04(4H, m), 2.36(3H, s), 2.97(2H, t), 3.24-3.50(2H, m), 4.13(2H, t), 7.03(1H, d), 7.54(1H, d) A-0424 400 MHz 1.90-2.02(4H, m), 3.01(2H, t), 3.45(2H, q), 4.05(2H, t), 7.13(1H, s), 7.46(1H, s) A-0425 400 MHz 1.94-2.03(4H, m), 3.01(2H, t), 3.31-3.43 (1H, m), 3.68-3.81(1H, m), 4.17(2H, t), 7.18 (2H, s) A-0432 400 MHz 1.62(2H, m), 1.70-1.95(4H, m), 2.31(3H, s), 2.92(2H, t), 3.32-3.48(2H, m), 4.11(2H, t), 6.98(1H, d), 7.54(1H, d) A-0436 400 MHz 1.55-1.70(2H, m), 1.75-1.93(4H, m), 2.92 (2H, t), 3.51(2H, q), 4.10(2H, t), 7.25(1H, d), 7.41(1H, d) A-0440 300 MHz 1.54-1.67(2H, m), 1.70-1.95(4H, m), 2.39 (3H, s), 2.92(2H, t), 3.33(2H, q), 4.01(2H, t), 7.06(1H, s), 7.24(1H, s) A-0480 400 MHz 1.49-1.53(4H, m), 1.71-1.82(4H, m), 2.17 (3H, s), 2.38(3H, s), 2.90(2H, t), 3.30(2H, q), 3.94(2H, t), 6.96(1H, s), 6.70(1H, s) A-0511 300 MHz 1.40-1.56(6H, m), 1.66-1.83(4H, m), 2.17 (3H, s), 2.38(3H, s), 2.88(1H, t), 3.31(2H, q), 3.93(2H, t), 6.96(1H, s), 7.00(1H, s) A-0512 300 MHz 1.41-1.52(6H, m), 1.68-1.86(4H, m), 2.28 (3H , s), 2.33(3H, s), 2.89(2H, t), 3.26-3.50 (2H, m), 4.03(2H, t), 7.01(1H, s), 7.36(1H, s) A-0544 300 MHz 1.81-2.01(4H, m), 2.31(3H, s), 2.90(2H, t), 3.31-3.48(2H, m), 4.13(2H, t), 6.82(1H, t), 6.99(1H, d), 7.54(1H, d)

(173) TABLE-US-00067 TABLE 67 Physical Property Compound No. (.sup.1H-NMR DATA, in CDCl.sub.3/TMS (ppm)) A-0554 400 MHz 1.57-1.63(2H, m), 1.75-1.89(4H, m), 2.31 (3H, s), 2.84(2H, t), 3.36-3.42(2H, m), 4.10 (2H, t), 6.81(1H, t), 7.00(1H, d), 7.54(1H, d) A-0557 400 MHz 1.57-1.63(2H, m), 1.72-1.84(4H, m), 2.38 (3H, s), 2.84(2H, t), 3.40(2H, q), 3.94(2H, t), 6.75(1H, dd), 6.81(1H, t), 7.00(1H, s), 7.11(1H, d) A-0570 400 MHz 1.49-1.56(4H, m), 1.70-1.81(4H, m), 2.41 (3H, s), 2.81(2H, t), 3.29(2H, q), 4.00(2H, t), 6.80(1H, t), 6.96(1H, d), 7.14(1H, d) A-0661 400 MHz 1.59-70(2H, m), 1.79-1.92(4H, m), 3.21 (2H, t), 3.41(2H, q), 4.04(2H, t), 7.21(1H, d), 7.25(2H, d) A-0664 300 MHz 2.17(3H, s), 2.34(2H, quint), 2.39(3H, s), 3.19(2H, t), 3.32(2H, q), 4.09(2H, t), 6.98 (1H, s), 7.01(1H, s) A-0678 400 MHz 1.50-1.62(4H, m), 1.83-1.92(4H, m), 2.96 (2H, t), 3.45(2H, q), 4.03(2H, t), 7.13(1H, s), 7.46(1H, s) A-0679 300 MHz 1.53-1.54(4H, m), 1.82-1.87(4H, m), 2.17 (3H, s), 2.38(3H, s), 2.96(2H, t), 3.31(2H, q), 3.94(2H, t), 6.96(1H, s), 6.70(1H, s) A-0681 300 MHz 1.40-1.56(6H, m), 1.75-1.88(4H, m), 2.17 (3H, s), 2.38(3H, s), 2.95(2H, t), 3.31(2H, q), 3.93(2H, t), 6.96(1H, s), 7.00(1H, s) A-0687 300 MHz 2.40(3H, s), 3.23(2H, q), 5.31(2H, s), 6.99 (1H, d), 7.12(1H, d), 7.46(1H, t), 7.57(1H, t), 7.63-7.80(2H, m) A-0745 300 MHz 2.42(3H, s) 3.24(2H, q) 5.14(2H, s), 7.00 (1H, d), 7.15(1H, d), 7.21-7.37(2H, m), 7.62(1H, dd) A-0747 300 MHz 2.41(3H, s), 3.21(2H, q), 5.17(2H, s), 7.00 (1H, d), 7.15(1H, d), 7.57(2H, d), 7.64(2H, d) A-0822 300 MHz 2.41(3H, s), 3.15(2H, t), 3.27(2H, q), 4.23 (2H, t), 6.96(1H, d), 7.11(1H, d), 7.11-7.19 (2H, m), 7.55(1H, t) A-0834 400 MHz 2.12(2H, quint), 2.41(3H, s), 2.82(2H, t), 3.27(2H, q), 4.01(2H, t), 6.96(1H, d), 7.11 (1H, d), 7.19-7.32(5H, m)

(174) TABLE-US-00068 TABLE 68 Physical Property Compound No. (.sup.1H-NMR DATA, in CDCl.sub.3/TMS (ppm)) A-0970 300 MHz 1.10(9H, s), 2.16(2H, t), 2.41(3H, s), 3.29 (2H, q), 4.11-4.20(4H, m), 6.95(1H, d), 7.14 (1H, d), 7.32(1H, s) A-0971 400 MHz 1.09(9H, s), 2.18(2H, t), 2.31(3H, s), 3.30- 3.50(2H, m), 4.16-4.20(4H, m), 6.98(1H, d), 7.32(1H, s), 7.57(1H, d) A-0998 400 MHz 2.40(3H, s), 3.26(2H, q), 4.26(2H, t), 4.51 (2H, t), 6.98(1H, d), 7.25(1H, dd), 7.33-7.40 (1H, m), 7.47(1H, t), 7.55-7.65(2H, m), 7.65 (1H, d), 8.13(1H, s) A-1032 400 MHz 2.42(3H, s), 3.09(3H, s), 3.29(2H, q), 4.25- 4.35(2H, m), 4.56-4.61(2H, m), 6.99(1H, d), 7.18(1H, d) A-1044 400 MHz 2.10(2H, quint), 2.01(3H, s), 3.29(2H, q), 3.87(2H, t), 4.10(2H, t), 5.40(2H, bs), 6.96 (1H, d), 7.18(1H, d) A-1072 400 MHz 1.83-1.97(4H, m), 2.85(2H, t), 3.41(2H, q), 4.05(2H, t), 7.20(1H, d), 7.23(1H, d) A-1101 300 MHz 1.40(2H, bs), 1.59-1.70(2H, m), 1.79-1.89 (2H, m), 2.41(3H, s), 2.78(2H, t), 3.29(2H, q), 4.03(2H, t), 6.95(1H, d), 7.15(1H, s) A-1116 400 MHz 1.80-1.93(4H, m), 2.42(3H, s), 3.29(2H, q), 3.43-3.54(2H, m), 4.06(2H, t), 6.62(1H, bs), 6.98(1H, d), 7.15(1H, d) A-1149 400 MHz 1.78-1.94(4H, m), 2.41(3H, s), 2.97(3H, s), 3.24(2H, t), 3.30(2H, q), 4.05(2H, t), 4.44 (1H, bs), 6.97(1H, d), 7.15(1H, d) A-1156 300 MHz 1.80-1.99(4H, m), 3.36-3.47(4H, m), 4.07 (2H, t), 5.15(1H, m), 7.23(1H, d), 7.25(1H, d) A-1201 400 MHz 1.48-1.57(2H, m), 1.75-1.88(4H, m), 2.41 (3H, s), 3.29(2H, q), 3.82(2H, t), 3.92(3H, s), 4.11(2H, t), 6.96(1H, s), 7.14(1H, s)

(175) TABLE-US-00069 TABLE 69 Physical Property Compound No. (.sup.1H-NMR DATA, in CDCl.sub.3/TMS (ppm)) B-0028 300 MHz 2.42(3H, s), 3.24(2H, q), 5.13(2H, s), 7.01 (1H, d), 7.15(1H, d), 7.30-7.38(2H, m), 8.60- 8.68(2H, m) B-0031 300 MHz 2.41(3H, s), 3.19-3.37(2H, m), 5.30(2H, s), 7.00(1H, d), 7.17(1H, d), 7.71(1H, d), 7.97 (1H, d), 8.86(1H, s) B-0057 300 MHz 2.15(2H, quint), 2.42(3H, s), 2.94(2H, t), 3.31(2H, q), 4.03(2H, t), 6.98(1H, d), 7.13 (1H, d), 7.62(1H, d), 7.72(1H, d), 8.60(1H, s) B-0060 300 MHz 2.32(2H, quint), 2.41(3H, s), 3.22(2H, t), 3.28(2H, q), 4.13(2H, t), 6.95(1H, d), 7.15 (1H, d), 7.88(1H, s), 8.70(1H, s) B-0063 300 MHz 2.44(3H, s), 3.29(2H, q), 5.33(2H, s), 7.04 (1H, d), 7.22(1H, d), 9.26(1H, s), 9.35(1H, s)

(176) TABLE-US-00070 TABLE 70 Physical Property Compound No. (.sup.1H-NMR DATA, in CDCl.sub.3/TMS (ppm)) C-0005 400 MHz 2.36(3H, s), 3.38(2H, q), 5.61(1H, brs), 6.69(1H, dd), 6.93(1H, s), 7.03(1H, d) C-0006 400 MHz 2.28(3H, s), 3.37-3.56(2H, m), 6.96(1H, dd), 7.12(1H, d), 7.73(1H, d), 8.04(1H, bs) C-0015 300 MHz 3.30-3.44(1H, m), 3.66-3.80(1H, m), 7.40(1H, s), 7.61(1H, s) C-0017 300 MHz 2.20(3H, s), 2.36(3H, s), 3.32(2H, q), 4.59(1H, s), 6.93(1H, s), 6.98(1H, s) C-0018 300 MHz 2.25(6H, s), 3.35-3.53(2H, m), 6.98 (1H, s), 7.63(1H, s), 7.69(1H, s)

(177) TABLE-US-00071 TABLE 71 Compound No. Specific Rotation ()-A-0086 104.4 (+)-A-0086 +103.6 ()-A-0434 120.3 (+)-A-0434 +119.3 ()-A-0479 120.6 (+)-A-0479 +115.2 ()-A-0481 93.2 (+)-A-0481 +96.5 ()-A-0764 86.4 (+)-A-0764 +88.5 ()-A-0767 117.0 (+)-A-0767 +122.8 ()-A-1215 99.2 (+)-A-1215 +98.1 ()-A-1218 120.4 (+)-A-1218 +121.6

(178) Next, there are specifically explained examples of formulating the present pest control agent by using the present alkyl phenyl sulfide derivative produced as above or the agriculturally acceptable salt thereof. The kinds and proportions of compounds and additives used in each formulation are not restricted to those shown in the following Formulation Examples and may be varied in a wide range. In the following explanation, parts (part) refer (refers) to mass parts (mass part).

[Formulation Example 1] Emulsifiable Concentrate

(179) TABLE-US-00072 A compound described in Table 1 to Table 41 10 parts Cyclohexanone 30 parts Polyoxyethylene alkyl aryl ether 11 parts Calcium alkylbenzenesulfonate 4 parts Methylnaphthalene 45 parts

(180) The above materials were dissolved homogeneously to obtain an emulsifiable concentrate.

[Formulation Example 2] Wettable Powder

(181) TABLE-US-00073 A compound described in Table 1 to Table 41 10 parts Sodium salt of naphthalenesulfonic acid- 0.5 part formalin condensate Polyoxyethylene alkyl aryl ether 0.5 part Diatomaceous earth 24 parts Clay 65 parts

(182) The above materials were mixed and ground to obtain a wettable powder.

[Formulation Example 3] Dust Formulation

(183) TABLE-US-00074 A compound described in Table 1 to Table 41 2 parts Diatomaceous earth 5 parts Clay 93 parts

(184) The above materials were mixed and ground to obtain a dust formulation.

[Formulation Example 4] Granule

(185) TABLE-US-00075 A compound described in Table 1 to table 41 5 parts Sodium salt of lauryl alcohol sulfate 2 parts Sodium ligninsulfonate 5 parts Carboxymethyl cellulose 2 parts Clay 86 parts

(186) The above materials were mixed homogeneously and ground. Thereto was added 20 parts of water, followed by kneading. The kneaded material was passed through an extrusion-granulator to obtain granules of 14 to 32 meshes. The granules were dried to obtain a granule.

[Formulation Example 5] Flowable Concentrate

(187) TABLE-US-00076 A compound described in Table 1 to Table 41 20 parts Polyoxyethylene styrenated phenyl ether 4 parts sulfate Ethylene glycol 7 parts Silicone AF-118N (produced by Asahi 0.02 part Chemical Industry Co. , Ltd. ) Water 68.98 parts

(188) The above materials were mixed for 30 minutes using a high-speed stirrer and then ground using a wet grinder to obtain a flowable concentrate.

(189) The next, the effect of the present pest control agent is shown by Test Examples.

[Test Example 1] Control Effect Test for Tetranychus urticae Koch (Two Spotted Spider Mite)

(190) A wettable powder prepared based on Formulation Example 2 was diluted with water into an active ingredient concentration of 4 ppm. In the solution were immersed soybean seedlings which had been inoculated with 35 female adults of two spotted spider mite. The soybean seedlings were dried in the air and placed in a thermostat of 25 C. After 13 days, the number of living female adults was examined and the control value of the active ingredient was determined using the calculation formula of the following Mathematical Expression 1. This test was conducted with no replication.
Control value=100[(number of living female adults after 13 days, in treated seedlings)/(number of living female adults after 13 days, in non-treated seedlings)]100[Mathematical Expression 1]

(191) Tests similar to the above were conducted using, as comparative compounds, compound Nos. 22 and 23 described in JP-A-1975-29744, compound Nos. 3, 4, 5, 6 described in JP-A-1976-19121 and compound Nos. 18, 19 and 36 described in JP-A-1988-41451. The structures of these comparative compounds are as follows.

(192) ##STR00144## ##STR00145##

(193) Compound Nos. of the compounds which gave, in the above test, a control value of 90 or above, are shown below. A-0013, A-0017, A-0018, A-0024, A-0047, A-0052, A-0055, A-0056, A-0075, A-0077, A-0078, A-0079, A-0085, A-0086, A-0088, A-0089, A-0090, A-0092, A-0094, A-0108, A-0113, A-0115, A-0116, A-0117, A-0120, A-0123, A-0125, A-0126, A-0130, A-0133, A-0141, A-0144, A-0145, A-0147, A-0157, A-0160, A-0164, A-0168, A-0170, A-0175, A-0181, A-0185, A-0204, A-0212, A-0216, A-0220, A-0222, A-0223, A-0224, A-0244, A-0257, A-0262, A-0271, A-0277, A-0316, A-0318, A-0319, A-0320, A-0321, A-0322, A-0324, A-0325, A-0326, A-0327, A-0328, A-0329, A-0330, A-0331, A-0338, A-0339, A-0340, A-0341, A-0343, A-0346, A-0347, A-0352, A-0353, A-0356, A-0359, A-0360, A-0363, A-0365, A-0368, A-0369, A-0379, A-0387, A-0388, A-0391, A-0392, A-0393, A-0394, A-0396, A-0406, A-0416, A-0418, A-0432, A-0434, A-0438, A-0439, A-0440, A-0441, A-0443, A-0444, A-0445, A-0446, A-0447, A-0448, A-0449, A-0471, A-0472, A-0473, A-0474, A-0475, A-0476, A-0477, A-0478, A-0479, A-0481, A-0482, A-0483, A-0484, A-0485, A-0487, A-0489, A-0495, A-0502, A-0503, A-0504, A-0505, A-0507, A-0508, A-0510, A-0524, A-0525, A-0526, A-0533, A-0536, A-0539, A-0543, A-0544, A-0553, A-0554, A-0555, A-0556, A-0557, A-0558, A-0559, A-0560, A-0561, A-0562, A-0563, A-0570, A-0571, A-0573, A-0574, A-0575, A-0576, A-0577, A-0578, A-0587, A-0588, A-0589, A-0590, A-0591, A-0592, A-0594, A-0599, A-0605, A-0606, A-0610, A-0611, A-0616, A-0617, A-0618, A-0622, A-0623, A-0625, A-0626, A-0631, A-0632, A-0638, A-0640, A-0642, A-0644, A-0665, A-0674, A-0683, A-0684, A-0686, A-0690, A-0692, A-0693, A-0694, A-0695, A-0697, A-0698, A-0703, A-0709, A-0710, A-0711, A-0712, A-0713, A-0716, A-0717, A-0724, A-0728, A-0734, A-0735, A-0736, A-0741, A-0743, A-0744, A-0745, A-0746, A-0748, A-0751, A-0752, A-0753, A-0754, A-0755, A-0757, A-0758, A-0761, A-0762, A-0763, A-0764, A-0765, A-0766, A-0767, A-0768, A-0769, A-0772, A-0773, A-0774, A-0775, A-0776, A-0778, A-0779, A-0780, A-0781, A-0782, A-0783, A-0784, A-0786, A-0787, A-0788, A-0789, A-0790, A-0791, A-0792, A-0793, A-0797, A-0798, A-0799, A-0800, A-0802, A-0805, A-0806, A-0807, A-0808, A-0809, A-0810, A-0813, A-0814, A-0816, A-0817, A-0818, A-0819, A-0820, A-0821, A-0822, A-0823, A-0824, A-0825, A-0826, A-0827, A-0838, A-0839, A-0844, A-0845, A-0853, A-0855, A-0856, A-0857, A-0860, A-0869, A-0870, A-0878, A-0880, A-0881, A-0885, A-0902, A-0913, A-0914, A-0915, A-0916, A-0917, A-0918, A-0921, A-0923, A-0924, A-0936, A-0940, A-0941, A-0942, A-0948, A-0956, A-0957, A-0969, A-0971, A-0973, A-0978, A-0979, A-0980, A-0982, A-0983, A-0984, A-0985, A-0988, A-0989, A-0990, A-0991, A-0992, A-1011, A-1032, A-1033, A-1052, A-1081, A-1087, A-1088, A-1107, A-1108, A-1112, A-1113, A-1119, A-1125, A-1126, A-1127, A-1128, A-1132, A-1136, A-1138, A-1140, A-1142, A-1149, A-1150, A-1151, A-1152, A-1154, A-1155, A-1156, A-1157, A-1158, A-1159, A-1164, A-1165, A-1166, A-1167, A-1175, A-1177, A-1178, A-1180, A-1181, A-1183, A-1185, A-1188, A-1190, A-1192, A-1195, A-1196, A-1200, A-1201, A-1207, A-1210, A-1211, B-0005, B-0006, B-0007, B-0008, B-0009, B-0010, B-0011, B-0017, B-0018, B-0019, B-0022, B-0023, B-0029, B-0055, B-0060, B-0063, B-0068, B-0070, B-0072, B-0073, B-0074, B-0075, B-0076, B-0078, B-0079, B-0080, B-0082, B-0084, B-0086, B-0088, B-0090, B-0092, B-0094, B-0096, B-0099, B-0102, B-0104, B-0106, B-0108

(194) Any of comparative compounds 22 and 23 (described in JP-A-1975-29744), 3, 4, 5 and 6 (described in JP-A-1976-19121) and 18, 19 and 36 (described in JP-A-1988-41451) showed no activity at a concentration of 4 ppm.

[Test Example 2] Insecticidal Activity Test for Nilaparvata lugens Stl (Brown Rice Planthopper)

(195) A wettable powder prepared based on Formulation Example 2 was diluted with water into an active ingredient concentration of 100 ppm. In the solution was immersed sprouting unhulled rice. They were placed in a 60-ml plastic cup. Thereinto were released 10 3-instar larvae of brown rice planthopper. The cup was covered with a lid and placed in a thermostat of 25 C. After 6 days, the number of living insects was counted and the mortality of insect was determined from the calculation formula of the following Mathematical Expression 2. This test was conducted with no replication.
Mortality (%)=100[(number of living insects after 6 days)/(number of tested insects)]100[Mathematical Expression 2]

(196) As in the case of Test Example 1, tests similar to the above were conducted using, as comparative compounds, compound Nos. 22 and 23 described in JP-A-1975-29744, compound Nos. 4, 5, 6 described in JP-A-1976-19121 and compound Nos. 18, 19 and 36 described in JP-A-1988-41451.

(197) Compound Nos. of the compounds which gave, in the above test, a mortality of 90% or above, are shown below. A-0001, A-0004, A-0005, A-0006, A-0007, A-0015, A-0018, A-0022, A-0023, A-0025, A-0032, A-0035, A-0037, A-0038, A-0039, A-0043, A-0044, A-0046, A-0047, A-0051, A-0052, A-0056, A-0070, A-0074, A-0075, A-0077, A-0078, A-0085, A-0086, A-0087, A-0088, A-0089, A-0090, A-0091, A-0092, A-0108, A-0122, A-0123, A-0125, A-0130, A-0133, A-0141, A-0144, A-0145, A-0147, A-0157, A-0159, A-0160, A-0163, A-0164, A-0167, A-0168, A-0169, A-0170, A-0172, A-0173, A-0175, A-0180, A-0181, A-0185, A-0186, A-0187, A-0188, A-0199, A-0200, A-0203, A-0205, A-0206, A-0208, A-0211, A-0212, A-0213, A-0214, A-0215, A-0216, A-0217, A-0218, A-0219, A-0220, A-0221, A-0222, A-0223, A-0224, A-0228, A-0229, A-0230, A-0243, A-0244, A-0253, A-0254, A-0256, A-0257, A-0259, A-0260, A-0262, A-0263, A-0266, A-0271, A-0277, A-0285, A-0307, A-0308, A-0311, A-0314, A-0317, A-0319, A-0324, A-0325, A-0328, A-0329, A-0338, A-0340, A-0341, A-0346, A-0360, A-0369, A-0379, A-0405, A-0406, A-0415, A-0416, A-0417, A-0418, A-0431, A-0432, A-0433, A-0434, A-0436, A-0437, A-0438, A-0439, A-0440, A-0446, A-0447, A-0448, A-0472, A-0473, A-0474, A-0475, A-0503, A-0504, A-0505, A-0535, A-0539, A-0543, A-0544, A-0553, A-0554, A-0556, A-0557, A-0570, A-0572, A-0574, A-0587, A-0610, A-0617, A-0625, A-0626, A-0631, A-0644, A-0683, A-0684, A-0703, A-0732, A-0734, A-0741, A-0743, A-0744, A-0745, A-0747, A-0751, A-0753, A-0755, A-0761, A-0763, A-0764, A-0765, A-0766, A-0772, A-0777, A-0778, A-0779, A-0780, A-0781, A-0786, A-0787, A-0788, A-0789, A-0797, A-0798, A-0809, A-0811, A-0813, A-0815, A-0821, A-0822, A-0823, A-0824, A-0825, A-0834, A-0838, A-0839, A-0844, A-0846, A-0847, A-0853, A-0855, A-0857, A-0877, A-0968, A-0969, A-0970, A-0971, A-0972, A-0973, A-0975, A-0976, A-0977, A-0978, A-0979, A-0981, A-0982, A-0983, A-0984, A-0985, A-0988, A-0991, A-0992, A-0998, A-1003, A-1004, A-1005, A-1006, A-1008, A-1009, A-1032, A-1033, A-1037, A-1044, A-1051, A-1087, A-1093, A-1094, A-1107, A-1125, A-1136, A-1140, A-1142, A-1158, A-1159, A-1177, A-1180, A-1185, A-1187, A-1188, A-1195, A-1210, A-1211, A-1212, A-1213, B-0003, B-0004, B-0005, B-0007, B-0012, B-0013, B-0022, B-0028, B-0029, B-0032, B-0033, B-0035, B-0051, B-0053, B-0055, B-0058, B-0059, B-0060, B-0063, B-0066, B-0086, B-0088, B-0093, B-0101, C-0001

(198) Any of comparative compounds 22 and 23 (described in JP-A-1975-29744), 4, 5 and 6 (described in JP-A-1976-19121) and 18, 19 and 36 (described in JP-A-1988-41451) each showed no activity even at a concentration of 100 ppm.