PLANT DISEASE CONTROL AGENT

Abstract

A plant disease control agent which contains a compound represented by formula (1) as an active ingredient.

##STR00001##

Claims

1. A plant disease control agent comprising a compound of formula (1) as an active ingredient, ##STR00281## in the formula (1), X.sup.1 and X.sup.4 are identical to or different from each other, represent a hydrogen atom, a fluorine atom, a chlorine atom or a trifluoromethyl group, at least one of X and X.sup.4 represents a fluorine atom or a trifluoromethyl group, X.sup.2 and X.sup.3 are identical to or different from each other, and represent a hydrogen atom, a fluorine atom, a chlorine atom or a methyl group, and, when one of X.sup.1, X.sup.2 and X.sup.4 represents a fluorine atom, any one of remaining two thereof does not represent a hydrogen atom, X.sup.a represents a group of formula (2), (3), (4) or (5), ##STR00282## in the formula (2), J represents an oxygen atom or a sulfur atom, A represents: a C1-12 alkyl group which may be substituted with one to three groups selected from the group consisting of groups belonging to a Group C, a thiol group, a methoxycarbonyl group, and a N-tert-butoxycarbonylamino group, a C2-8 alkenyl group which may be substituted with one to three groups selected from the groups belonging to the Group C; a C2-8 alkynyl group which may be substituted with one to three groups selected from the groups belonging to the Group C; a C1-8 alkylcarbonyl group which may be substituted with one to three groups selected from the groups belonging to the Group C; a C1-4 alkyloxy group which may be substituted with one to three groups selected from the groups belonging to the Group C; a C1-8 alkylsulfonyl group which may be substituted with one to three groups selected from the groups belonging to the Group C; a phenylcarbonyl group which may be substituted with one to four groups selected from the group consisting of groups belonging to a Group D, a benzyl group, a phenyl group, and a phenoxy group; a phenylsulfonyl group which may be substituted with one to four groups selected from the groups belonging to the Group D; a phenyl group which may be substituted with one to five groups selected from the group consisting of the groups belonging to the Group D, a phenoxy group, and a benzyl group, a 5, 6, 7, 8-tetrahydronaphthyl group, a naphthyl group, a hetero ring group which may be substituted with one to four groups selected from the groups belonging to the Group D, the hetero ring group being a group selected from a Group E), or a group of formula (2A), in the formula (2A), X.sup.1, X.sup.2, X.sup.3 and X.sup.4 are the same as defined in the formula (1), ##STR00283## wherein, when A represents the group of the formula (2A), Q represents a divalent group of formula: —O—(CH.sub.2).sub.n—O—, a divalent group of formula: —NH—(CH.sub.2).sub.n—O—, a divalent group of formula: —NH—(CH.sub.2).sub.n—NH—, a divalent group of formula: —O—CH.sub.2—CH═CH—CH.sub.2—O—, a divalent group of formula: —NH—CH.sub.2—CH═CH—CH.sub.2—O—, a divalent group of formula: —NH—CH.sub.2—CH═CH—CH.sub.2—NH—, a cyclohexane-1,4-diyldioxy group, a cyclohexane-1,4-diyldiamino group, a divalent group of formula: —NH-(cyclohexane-1,4-diyl)-O—, a 1,3-phenylenediamino group, a 1,4-phenylenediamino group, a 1,4-phenylenedioxy group, a divalent group of formula: —NH-(1,4-phenylene)-O—, or a divalent group of formula (2B), fin the formula (2B), G represents an oxygen atom, a sulfur atom or a divalent group of formula: —SO.sub.2—, in which n represents an integer of 2 to 8, and ##STR00284## when A does not represent the group of the formula (2A), Q represents an oxygen atom, a sulfur atom, a divalent group of formula: —NH—, or a divalent group of formula: —N(CH.sub.3)—, in the formula (3), Aa represents a piperidin-1-yl group, a 1-methyl-1-1H-pyrrol-2-yl group, a morpholin-4-yl group, an indolin-1-yl group, a benzoisothiazol-3(2H)-one-1,1-dioxide-2-yl group, a piperazin-1-yl group, an azetidin-1-yl group, a 2,5-dioxopyrrolidin-1-yl group, a 3-oxoisothiazol-2(3H)-yl group, a benzo[d]isothiazol-2(3H)-yl group, a 1,1-dioxo-3-oxobenzo[d]isothiazol-2(3H)-yl group, a 5,6-dihydro-4H-1,3-oxazin-2-yl group, a 1H-pyrrol-2-yl group or an isoindolin-2-yl group, in the formula (4), Qb represents an oxygen atom, a sulfur atom, a divalent group of formula: —NH— or a divalent group of formula: —N(CH.sub.3)—, Ab represents: a hydrogen atom; a C1-10 alkyl group which may be substituted with one to three groups selected from the group consisting of the groups belonging to the Group C, a methoxycarbonyl group, and a N-tert-butoxycarbonylamino group; a C2-8 alkenyl group which may be substituted with one to three groups selected from the groups belonging to the Group C; a C2-8 alkynyl group which may be substituted with one to three groups selected from the groups belonging to the Group C; a C1-8 alkylcarbonyl group which may be substituted with one to three groups selected from the groups belonging to the Group C, a phenylcarbonyl group, or a hetero ring group which may be substituted with one to four groups selected from the groups belonging to the Group D, the hetero ring group being a group selected from the Group E, in the formula (5), m represents an integer of 1 to 3, Z represents a hydrogen atom, a halogen atom or a methyl group, the Group C consists of halogen atoms, a hydroxyl group, an amino group, a 5-methyl-1,3-dioxol-2-one-4-yl group, a phenylcarbonyl group, pyridyl groups which may be substituted with one to three groups selected from the groups belonging to the Group D, and phenyl groups which may be substituted with one to four groups selected from the groups belonging to the Group D, the Group D consists of halogen atoms, a hydroxyl group, an amino group, a methylthio group, C1-4 alkyl groups which may be substituted with one to three halogen atoms, C1-4 alkyloxy groups which may be substituted with one to three halogen atoms, C1-4 alkylcarbonyl groups, a methoxycarbonyl group, an ethoxycarbonyl group, a benzylaminocarbonyl group, an acetoxy group, a nitro group, and a cyano group, and the Group E consists of a pyridyl group, a thiazolyl group, a pyrazinyl group, a pyridazinyl group, an isothiazolyl group, an isoxazolyl group, a pyrimidinyl group, a benzimidazolyl group, a thienyl group, a furanyl group, a benzoxanyl group, a 2,3-dihydrobenzo[b][1,4]dioxin-6-yl group, a dihydrothiazolyl group, a benzothiazolyl group, a benzoisothiazolyl group, a benzisothiazole-3(2H)-one-1,1-dioxidyl group, a dibenzofuranyl group, and a triazolyl group.

2. The plant disease control agent according to claim 1, wherein X.sup.1, X.sup.2, X.sup.3 and X.sup.4 in the formula (1) are hydrogen atoms or fluorine atoms.

3. The plant disease control agent according to claim 1, wherein, in the formula (1), X.sup.1 and X.sup.4 represent fluorine atoms, and X.sup.2 or X.sup.3 represents a hydrogen atom.

4. The plant disease control agent according to claim 1, wherein, in the formula (1), X.sup.1 and X.sup.4 represent fluorine atoms, and X.sup.2 and X.sup.3 represent hydrogen atoms.

5. The plant disease control agent according to claim 1, wherein X.sup.a in the formula (1) represents a group of the formula (2), and J in the formula (2) represents an oxygen atom.

6. The plant disease control agent according to claim 1, wherein X.sup.a in the formula (1) represents a group of the formula (2), and Q in the formula (2) represents a divalent group of formula: —NH—.

7. The plant disease control agent according to claim 1, wherein X.sup.a in the formula (1) represents a group of the formula (2), and Q in the formula (2) represents an oxygen atom.

8. The plant disease control agent according to claim 1, wherein X.sup.a in the formula (1) represents a group of the formula (2), and A in the formula (2) represents: a C1-12 alkyl group which may be substituted with one to three groups selected from the Group C; a C2-8 alkenyl group which may be substituted with one to three groups selected from the Group C; a C2-8 alkynyl group which may be substituted with one to three groups selected from the Group C; a C1-8 alkylcarbonyl group which may be substituted with one to three groups selected from the Group C; a C1-4 alkyloxy group which may be substituted with one to three groups selected from the Group C; a phenylcarbonyl group which may be substituted with one to four groups selected from the group consisting of the groups belonging to the Group D, a benzyl group, a phenyl group, and a phenoxy group; a phenylsulfony group which may be substituted with one to four groups selected from the Group D; a phenyl group which may be substituted with one to five groups selected from the group consisting of the groups belonging to the Group D, a phenoxy group and a benzyl group; or a hetero ring group which may be substituted with one to four groups selected from the Group D.

9. A compound of formula (1), excluding a compound of formula (2) wherein J and Q represent oxygen atoms, A represents a methyl group, an ethyl group or a cyclohexyl group, or a compound of the formula (2) wherein J represents an oxygen atom, Q represents a divalent group of formula: —NH—, and A represents a 3-chloro-4-fluorophenyl group, ##STR00285## in the formula (1), X.sup.1 and X.sup.4 are identical to or different from each other, represent a hydrogen atom, a fluorine atom, a chlorine atom or a trifluoromethyl group, at least one of X.sup.1 and X.sup.4 represents a fluorine atom or a trifluoromethyl group, X.sup.2 and X.sup.3 are identical to or different from each other, and represent a hydrogen atom, a fluorine atom, a chlorine atom or a methyl group, and, when one of X.sup.1, X.sup.2 and X.sup.4 represents a fluorine atom, any one of remaining two thereof does not represent a hydrogen atom, X.sup.a represents a group of formula (2), (3), (4) or (5), ##STR00286## in the formula (2), J represents an oxygen atom or a sulfur atom, A represents: a C1-12 alkyl group which may be substituted with one to three groups selected from the group consisting of groups belonging to a Group C, a thiol group, a methoxycarbonyl group, and a N-tert-butoxycarbonylamino group; a C2-8 alkenyl group which may be substituted with one to three groups selected from the groups belonging to the Group C, a C2-8 alkynyl group which may be substituted with one to three groups selected from the groups belonging to the Group C; a C1-8 alkylcarbonyl group which may be substituted with one to three groups selected from the groups belonging to the Group C, a C1-4 alkyloxy group which may be substituted with one to three groups selected from the groups belonging to the Group C, a C1-8 alkylsulfonyl group which may be substituted with one to three groups selected from the groups belonging to the Group C, a phenylcarbonyl group which may be substituted with one to four groups selected from the group consisting of groups belonging to a Group D, a benzyl group, a phenyl group, and a phenoxy group, a phenylsulfonyl group which may be substituted with one to four groups selected from the groups belonging to the Group D, a phenyl group which may be substituted with one to five groups selected from the group consisting of the groups belonging to the Group D, a phenoxy group, and a benzyl group, a 5, 6, 7, 8-tetrahydronaphthyl group, a naphthyl group, a hetero ring group which may be substituted with one to four groups selected from the groups belonging to the Group D, the hetero ring group being a group selected from a Group E, or a group of formula (2A), in the formula (2A), X.sup.1, X.sup.2, X.sup.3 and X.sup.4 are the same as defined in the formula (1), ##STR00287## wherein, when A represents the group of the formula (2A), Q represents a divalent group of formula: —O—(CH.sub.2).sub.n—O—, a divalent group of formula: —NH—(CH.sub.2).sub.n—O—, a divalent group of formula: —NH—(CH.sub.2).sub.n—NH—, a divalent group of formula: —O—CH.sub.2—CH═CH—CH.sub.2—O—, a divalent group of formula: —NH—CH.sub.2—CH═CH—CH.sub.2—O—, a divalent group of formula: —NH—CH.sub.2—CH═CH—CH.sub.2—NH—, a cyclohexane-1,4-diyldioxy group, a cyclohexane-1,4-diyldiamino group, a divalent group of formula: —NH-(cyclohexane-1,4-diyl)-O—, a 1,3-phenylenediamino group, a 1,4-phenylenediamino group, a 1,4-phenylenedioxy group, a divalent group of formula: —NH-(1,4-phenylene)-O—, or a divalent group of formula (2B), in the formula (2B), G represents an oxygen atom, a sulfur atom or a divalent group of formula: —SO.sub.2—, in which n represents an integer of 2 to 8, and ##STR00288## when A does not represent the group of the formula (2A), Q represents an oxygen atom, a sulfur atom, a divalent group of formula: —NH—, or a divalent group of formula: —N(CH.sub.3)—, in the formula (3), Aa represents a piperidin-1-yl group, a 1-methyl-1-1H-pyrrol-2-yl group, a morpholin-4-yl group, an indolin-1-yl group, a benzoisothiazol-3(2H)-one-1,1-dioxide-2-yl group, a piperazin-1-yl group, an azetidin-1-yl group, a 2,5-dioxopyrrolidin-1-yl group, a 3-oxoisothiazol-2(3H)-yl group, a benzo[d]isothiazol-2(3H)-yl group, a 1,1-dioxo-3-oxobenzo[d]isothiazol-2(3H)-yl group, a 5,6-dihydro-4H-1,3-oxazin-2-yl group, a 1H-pyrrol-2-yl group or an isoindolin-2-yl group, in the formula (4), Qb represents an oxygen atom, a sulfur atom, a divalent group of formula: —NH— or a divalent group of formula: —N(CH.sub.3)—, Ab represents: a C1-10 alkyl group which may be substituted with one to three groups selected from the group consisting of groups belonging to the Group C, a methoxycarbonyl group, and a N-tert-butoxycarbonylamino group; a C2-8 alkenyl group which may be substituted with one to three groups selected from the groups belonging to the Group C; a C2-8 alkynyl group which may be substituted with one to three groups selected from the groups belonging to the Group C; a C1-8 alkylcarbonyl group which may be substituted with one to three groups selected from the groups belonging to the Group C; or a hetero ring group which may be substituted with one to four groups selected from the groups belonging to the Group D, the hetero ring group being a group selected from the Group E, in the formula (5), m represents an integer of 1 to 3, Z represents a hydrogen atom, a halogen atom or a methyl group, the Group C consists of halogen atoms, a hydroxyl group, an amino group, a 5-methyl-1,3-dioxol-2-one-4-yl group, a phenylcarbonyl group, pyridyl groups which may be substituted with one to three groups selected from the groups belonging to the Group D, and phenyl groups which may be substituted with one to four groups selected from the groups belonging to the Group D, the Group D consists of halogen atoms, a hydroxyl group, an amino group, a methylthio group, C1-4 alkyl groups which may be substituted with one to three halogen atoms, C1-4 alkyloxy groups which may be substituted with one to three halogen atoms, C1-4 alkylcarbonyl groups, a methoxycarbonyl group, an ethoxycarbonyl group, a benzylaminocarbonyl group, an acetoxy group, a nitro group, and a cyano group, and the Group E consists of a pyridyl group, a thiazolyl group, a pyrazinyl group, a pyridazinyl group, an isothiazolyl group, an isoxazolyl group, a pyrimidinyl group, a benzimidazolyl group, a thienyl group, a furanyl group, a benzoxanyl group, a 2,3-dihydrobenzo[b][1,4]dioxin-6-yl group, a dihydrothiazolyl group, a benzothiazolyl group, a benzoisothiazolyl group, a benzisothiazole-3(2H)-one-1,1-dioxidyl group, a dibenzofuranyl group and a triazolyl group.

10. The compound according to claim 9, wherein X.sup.1, X.sup.2, X.sup.3 and X.sup.4 in the formula (1) are hydrogen atoms or fluorine atoms.

11. The compound according to claim 9, wherein, in the formula (1), X.sup.1 and X.sup.4 represent fluorine atoms, and X.sup.2 or X.sup.3 represents a hydrogen atom.

12. The compound according to claim 9, wherein, in the formula (1), X.sup.1 and X.sup.4 represent fluorine atoms, and X.sup.2 and X.sup.3 represent hydrogen atoms.

13. The compound according to claim 9, wherein X.sup.a in the formula (1) represents a group of the formula (2), and J in the formula (2) represents an oxygen atom.

14. The compound according to claim 9, wherein X.sup.a in the formula (1) represents a group of the formula (2), and Q in the formula (2) represents a divalent group of formula: —NH—.

15. The compound according to claim 9, wherein X.sup.a in the formula (1) represents a group of the formula (2), and Q in the formula (2) represents an oxygen atom.

16. The compound according to claim 9, wherein X.sup.a in the formula (1) represents a group of the formula (2), and A in the formula (2) represents: a C1-12 alkyl group which may be substituted with one to three groups selected from the Group C; a C2-8 alkenyl group which may be substituted with one to three groups selected from the Group C; a C2-8 alkynyl group which may be substituted with one to three groups selected from the Group C; a C1-8 alkylcarbonyl group which may be substituted with one to three groups selected from the Group C; a C1-4 alkyloxy group which may be substituted with one to three groups selected from the Group C; a phenylcarbonyl group which may be substituted with one to four groups selected from the group consisting of the groups belonging to the Group D, a benzyl group, a phenyl group, and a phenoxy group; a phenylsulfony group which may be substituted with one to four groups selected from the Group D; a phenyl group which may be substituted with one to five groups selected from the group consisting of the groups belonging to the Group D, a phenoxy group and a benzyl group; or a hetero ring group which may be substituted with one to four groups selected from the Group D.

17. A method for controlling plant disease, comprising: contacting a plant disease control agent of claim 1 with a plant body or a seed, or formulating the plant disease control agent in a cultivation bed.

18. A method for controlling plant disease, comprising: contacting a compound of claim 9 with a plant body or a seed, or formulating the compound in a cultivation bed.

Description

EXAMPLES

[0343] Hereinafter, the present invention will be explained further specifically by illustrating examples; however, the scope of the present invention is not limited to these examples.

[0344] Hereinafter, the below-mentioned abbreviated words may be used in the examples.

[0345] ESI: Electrospray ionization

[0346] MS: Mass spectrum

[0347] IR: Infrared absorption spectrum

[0348] n: normal

[0349] tert: tertiary

Example 1

[0350] 2,3,6-trifluoroisonicotinic acid (1.76 g) was dissolved in N,N-dimethylformamide (10 mL), followed by adding bromoethane (1.08 g) and potassium carbonate (1.38 g) to the solution, and then conducting stirring at 80° C. for 2 hours. Then, the reaction mixture was cooled to room temperature, ethyl acetate was added thereto, the mixture was subjected to extraction with water, an organic layer was dried with anhydrous magnesium sulfate, and then the solvent was distilled off. The residue was purified by silica gel chromatography to obtain a compound of Example 1-117 (yield 1.44 g).

Example 2

[0351] 2,3,6-trifluoroisonicotinic acid (5.28 g) was dissolved in thionyl chloride (30 mL), followed by heating the mixture to reflux for 1 hour. The resultant was concentrated, the concentrate was dissolved in acetonitrile (30 mL), and then 3-chloro-4-methylaniline (5.64 g) and pyridine (3.20 g) was added to the solution, followed by heating the mixture to reflux for 1 hour. Then, the reaction mixture was cooled to room temperature, ethyl acetate was added thereto, the mixture was washed sequentially with 1N hydrochloric acid and 1N sodium hydroxide, an organic layer was dried with anhydrous magnesium sulfate, and then the solvent was distilled off. The residue was purified by silica gel chromatography to obtain a compound of Example 1-30 (yield 7.70 g).

Example 3

[0352] 2,3,6-trifluoro-4-pyridinemethanol (106 mg) was dissolved in dichloromethane (8 mL), acetyl chloride (65 mg) was added to the solution, the mixture was cooled to 0° C., N,N-diisopropylethylamine (130 mg) was added thereto, and then the mixture was stirred at room temperature overnight. Then, the solvent was distilled off, the resultant was dissolved in diethyl ether, the solution was washed sequentially with saturated sodium carbonate, 2% hydrochloric acid, and saturated brine, and the resultant organic layer was dried with anhydrous magnesium sulfate. The solvent was distilled off using an evaporator, and then the residue was purified by silica gel chromatography to obtain a compound of Example 3-1 (yield 63.2 mg).

Example 4

[0353] 2,6-difluoroisonicotinic acid (50 mg) was dissolved in chloroform (3.1 mL), and then aniline (29 μL), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (65 mg), and 4-dimethylaminopyridine (catalytic amount) were added to the solution, followed by stirring the mixture at room temperature for 3 hours. Then, water was added to the reaction mixture, and then the mixture was subjected to extraction with ethyl acetate, followed by conducting washing sequentially with saturated ammonium chloride and saturated sodium hydrogen carbonate. The resultant organic layer was dried with anhydrous sodium sulfate, and then the solvent was distilled off. The residue was purified by silica gel chromatography to obtain a compound of Example 1-143 (yield 66.3 mg).

Example 5

[0354] 2,3,6-trifluoroisonicotinic acid (30 mg) was dissolved in chloroform (3.1 mL), and then ethylene diamine (6.0 μL), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (38 mg), 1-hydroxybenzotriazole (27 mg), and triethylamine (30 μL) were added to the solution, followed by stirring the mixture at room temperature overnight. 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (38 mg) and 1-hydroxybenzotriazole (27 mg) were added to the resultant again, and then the mixture was stirred at room temperature for 3 hours. Then, water was added to the reaction mixture, and then the resultant was subjected to extraction with ethyl acetate, followed by conducting washing sequentially with saturated ammonium chloride and saturated sodium hydrogen carbonate. The resultant organic layer was dried with anhydrous sodium sulfate, and then the solvent was distilled off. The residue was purified by silica gel chromatography to obtain a compound of Example 1-150 (yield 20.1 mg).

Example 6

[0355] 2,3,6-trifluoroisonicotinic acid (100 mg) was dissolved in N,N-dimethylformamide (5.6 mL), and then 2-chloroethylamine hydrochloride (79 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (128 mg), 1-hydroxybenzotriazole (92 mg), and triethylamine (101 L) were added to the solution, followed by stirring the mixture at room temperature for 3 hours. Then, water was added to the reaction mixture, and the resultant was subjected to extraction with ethyl acetate, followed by conducting washing sequentially with saturated ammonium chloride and saturated sodium hydrogen carbonate. The resultant organic layer was dried with anhydrous sodium sulfate, the solvent was distilled off, and then the residue was purified by silica gel chromatography to obtain N-(2-chloroethyl)-2,3,6-trifluoroisonicotinamide (yield 100 mg).

[0356] The obtained N-(2-chloroethyl)-2,3,6-trifluoroisonicotinamide (20 mg) was dissolved in tetrahydrofuran (8.4 mL), and then 55% sodium hydride (3.8 mg) was added to the solution under ice-cooling, followed by stirring the mixture for 3 hours. Then, water was added to the reaction mixture, subjected to extraction with ethyl acetate, the resultant organic layer was dried with anhydrous sodium sulfate, and then the solvent was distilled off. The residue was purified by silica gel chromatography to obtain a compound of Example 4-2 (yield 16 mg).

Example 7

[0357] 2,6-difluoroisonicotinic acid (80 mg) was dissolved in acetonitrile (1 mL), and then cyclohexyl alcohol (50 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (96 mg), and 4-dimethylaminopyridine (61 mg) were added to the solution, followed by stirring the mixture at room temperature for 24 hours. Then, water was added to the reaction mixture, and then the resultant was subjected to extraction with ethyl acetate, followed by conducting washing sequentially with saturated sodium hydrogen carbonate aqueous solution and saturated sodium chloride aqueous solution. The resultant organic layer was dried with anhydrous sodium sulfate, and then the solvent was distilled off. The residue was purified by preparative TLC to obtain a compound of Example 1-205 (yield 42 mg).

Example 8

[0358] 2,3,6-trifluoroisonicotinic acid (177 mg, 1.0 mmol) was dissolved in dichloroethane, and then thionyl chloride (1 mL) was added to the solution, followed by heating the mixture to reflux for 2 hours while conducting stirring. The solvent was distilled off using an evaporator, and then nitromethane (3 mL), 1-methylpyrrole (54 mg, 0.67 mmol), and zinc trifluoromethanesulfonate (II) (24 mg, 0.066 mmol) were added to the resultant, followed by stirring the mixture at room temperature overnight. Sodium hydrogen carbonate was added to the reaction mixture, and then water was added to the mixture to conduct extraction with chloroform. The resultant organic layer was dried with anhydrous sodium sulfate, and the solvent was distilled off using an evaporator, followed by purifying the residue by silica gel chromatography (mobile phase:hexane/ethyl acetate=1/1 (volume ratio)), and then conducting washing with hexane to obtain compound 2-2 (yield 44 mg, 0.18 mmol, 27% yield).

[0359] In accordance with the method of Examples 1 to 8, compounds of Examples 1-1 to 1-218, represented by formula (2″) and shown in the below-mentioned Tables 13 to 34, were prepared. In addition, compounds of Examples 2-1 to 2-5, represented by formula (3′) and shown in the below-mentioned Table 35, were prepared. In addition, compounds of Examples 3-1 and 3-2, represented by formula (4′) and shown in the below-mentioned Table 36, were prepared. In addition, compounds of Examples 4-1 to 4-4, represented by formula (5′) and shown in the below-mentioned Table 37, were prepared.

[0360] Data of MS, IR, and H-NMR of each compounds of formula (2″), (3′), (4′) or (5′), as well as those of the compounds obtained in Examples 1 to 8, are shown in Tables 13 to 37. Deuterated acetone was used as a solvent to conduct H-NMR measurement (400 MHz, 500 MHz or 600 MHz) of compounds of Examples 1-8, 1-69, 1-175, 1-176 and 4-2, a mixture of deuterated chloroform and deuterated methanol at a ratio of 1:1 was used as a solvent to conduct .sup.1H-NMR measurement of a compound of Example 1-93, and deuterated chloroform was used as a solvent to conduct .sup.1H-NMR measurement of compounds of other examples. MS was measured by ESI-MS method. IR was measured by the KBr method.

[0361] The compounds of Examples 1-1 to 1-218, represented by the formula (2″), are shown in Tables 13 to 34.

##STR00043##

TABLE-US-00013 TABLE 13 .sup.1H-NMR (measured at 400 MHz, 500 MHz, ESI MS (m/z) or Example Formula or 600 MHz) δ ppm IR (KBr) cm.sup.−1 1-1 [00044] 1.27 (d, 6H), 3.47 (s, 3H), 4.41-4.47 (m, 1H), 6.63-6.65 (m, 2H), 6.68-6.69 (m, 1H), 6.76-6.79 (m, 1H), 7.13-7.15 (m, 1H) m/z = 325 (M + H) 1-2 [00045] 3.50 (3H, s), 6.70 (1H, m), 7.11 (2H, m), 7.30 (3H, m) IR 1653, 1471, 1440, 1395, 1025, 701 1-3 [00046] 1.80 (4H, m), 2.76 (4H, m), 7.07 (1H, d), 7.28 (1H, d), 7.33 (1H, m), 7.45 (1H, m), 8.17 (1H, br) 1-4 [00047] 1.60 (1H, br), 7.79 (1H, s) m/z = 393 (M + H) 1-5 [00048] 7.36 (2H, m), 7.56 (1H, m), 8.49 (1H, dd) m/z = 321 (M + H) 1-6 [00049] 2.24 (6H, s), 2.31 (3H, s), 6.97 (2H, s), 7.49 (1H, m), 7.72 (1H, br) IR 1655, 1541, 1471, 1432, 1377, 1032 1-7 [00050] 2.28 (6H, s), 7.17 (3H, m), 7.46 (1H, m), 7.80 (1H, br) IR 1659, 1541, 1473, 1380, 1033 1-8 [00051] 7.20 (2H, m), 7.32 (1H, m), 7.47 (2H, m) m/z = 293 (M + H) 1-9 [00052] 4.29 (4H, m), 6.88 (1H, d), 7.01 (1H, dd), 7.28 (1H, d), 7.51 (1H, m), 8.10 (1H, br) m/z = 311 (M + H) 1-10 [00053] 7.17 (1H, dt), 7.37 (1H, t), 7.47 (1H, dd), 7.55 (1H, m), 8.51 (1H, d), 8.99 (1H, br) m/z = 224 (M + H)

TABLE-US-00014 TABLE 14 .sup.1H-NMR (measured at 400 MHz, 500 MHz, ESI MS (m/z) or Example Formula or 600 MHz) δ ppm IR (KBr) cm.sup.−1 1-11 [00054] 7.55 (1H, m), 8.55 (2H, m), 8.89 (1H, d), 9.19 (1H, br) m/z = 323 (M + H) 1-12 [00055] 3.94 (2H, t), 3.40 (2H, t), 7.32 (1H, m) m/z = 262 (M + H) 1-13 [00056] 3.95 (3H, s), 7.49 (1H, m), 7.57 (1H, d), 8.23 (1H, d), 11.37 (1H, br) m/z = 317 (M + H) 1-14 [00057] 2.36 (3H, s), 7.19 (1H, t), 7.30 (2H, m), 7.56 (1H, m), 8.01 (1H, d) IR 1655, 1546, 1459, 1370, 1033 1-15 [00058] 7.53 (1H, m), 8.36 (1H, t), 8.49 (1H, d), 8.02 (1H, br), 9.65 (1H, d) m/z = 255 (M + H) 1-16 [00059] 7.17 (1H, dd), 7.49 (1H, m), 7.81 (1H, dt), 8.30 (1H, d), 8.37 (1H, d) m/z = 254 (M + H) 1-17 [00060] 7.15 (1H, t), 7.42 (1H, m), 8.68 (1H, d), 8.85 (1H, br) m/z = 255 (M + H) 1-18 [00061] 7.14 (1H, d), 7.50 (1H, d), 7.53 (1H, m) m/z = 260 (M + H) 1-19 [00062] 7.50 (1H, m), 7.78 (2H, s), 8.21 (1H, br) m/z = 355 (M + H) 1-20 [00063] 3.85 (s, 3H), 3.90 (s, 6H), 6.93 (s, 2H), 7.49-7.50 (m, 1H), 8.19-8.22 (m, 1H) m/z = 343 (M + H)

TABLE-US-00015 TABLE 15 .sup.1H-NMR (measured at 400 MHz, 500 MHz, ESI MS (m/z) or Example Formula or 600 MHz) δ ppm IR (KBr) cm.sup.−1 1-21 [00064] 7.21 (2H, m), 7.50 (1H, m), 7.74 (1H, m) m/z = 289 (M + H) 1-22 [00065] 3.91 (3H, s), 3.93 (3H, s), 6.88 (1H, d), 7.05 (1H, dd), 7.39 (1H, d), 7.51 (1H, m), 8.19 (1H, br) m/z = 313 (M + H) 1-23 [00066] 2.27 (3H, s), 2.29 (3H, s), 7.16 (1H, d), 7.36 (1H, dd), 7.40 (1H, d), 7.51 (1H, m), 8.13 (1H, br) m/z = 281 (M + H) 1-24 [00067] 7.23 (1H, s), 7.49 (1H, m), 7.60 (1H, s), 8.20 (1H, br) m/z = 321 (M + H) 1-25 [00068] 3.82 (6H, s), 6.35 (1H, t), 6.85 (2H, d), 7.49 (1H, m), 8.16 (1H, br) m/z = 313 (M + H) 1-26 [00069] 2.35 (6H, s), 6.89 (1H, s), 7.26 (2H, s), 7.51 (1H, m), 8.13 (1H, br) m/z = 281 (M + H) 1-27 [00070] 4.01 (2H, s), 7.08 (1H, d), 7.20 (2H, d), 7.24-7.35 (4H, m), 7.43 (1H, s), 7.51 (2H, m) m/z = 343 (M + H) 1-28 [00071] 2.41 (3H, s), 7.26 (1H, m), 7.46 (1H, dd), 7.51 (1H, m), 7.91 (1H, d), 8.17 (1H, br) m/z = 345 (M + H) 1-29 [00072] 7.19 (1H, t), 7.45 (1H, m), 7.51 (1H, m), 7.85 (1H, dd), 8.21 (1H, br) m/z = 305 (M + H) 1-30 [00073] 2.40 (3H, s), 7.27 (1H, d), 7.40 (1H, dd), 7.53 (1H, m), 7.77 (1H, d) m/z = 301 (M + H)

TABLE-US-00016 TABLE 16 .sup.1H-NMR (measured at 400 MHz, 500 MHz, ESI MS (m/z) or Example Formula or 600 MHz) δ ppm IR (KBr) cm.sup.−1 1-31 [00074] 7.51 (1H, m), 7.61 (1H, d), 7.73 (1H, d), 7.95 (1H, s), 8.34 (1H, br) m/z = 355 (M + H) 1-32 [00075] 7.24 (1H, dt), 7.34 (1H, t), 7.46 (1H, dd), 7.51 (1H, m), 7.78 (1H, dd), 8.21 (1H, br) m/z = 287 (M + H) 1-33 [00076] 2.36 (3H, s), 6.67 (1H, s), 7.54 (1H, m), 9.46 (1H, br) m/z = 284 (M + H) 1-34 [00077] 7.53 (3H, m), 7.79 (1H, m), 8.10 (1H, s), 8.29 (1H, br) m/z = 278 (M + H) 1-35 [00078] 7.33 (1H, t), 7.47 (1H, m), 7.71 (2H, m), 8.51 (1H, d), 8.86 (1H, br) m/z = 278 (M + H) 1-36 [00079] 7.06 (1H, d), 7.10 (1H, d), 7.54 (1H, m), 9.54 (1H, br) m/z = 283 (M + H) 1-37 [00080] 1.42 (3H, t), 4.41 (2H, q), 7.51 (2H, m), 7.92 (1H, d), 8.01 (1H, d), 8.14 (1H, s), 8.31 (1H, br) m/z = 325 (M + H) 1-38 [00081] 1.44 (3H, t), 4.07 (2H, q), 6.77 (1H, dd), 7.10 (1H, dd), 7.30 (1H, t), 7.36 (1H, t), 7.51 (1H, m), 8.20 (1H, br) m/z = 297 (M + H) 1-39 [00082] 2.28 (3H, s), 7.17 (1H, dd), 7.20 (1H, t), 7.51 (1H, m), 7.55 (1H, dd), 8.20 (1H, br) m/z = 285 (M + H) 1-40 [00083] 2.44 (3H, s), 7.26 (1H, m), 7.50 (1H, m), 7.53 (1H, dd), 8.11 (1H, d), 8.14 (1H, br) m/z = 393 (M + H)

TABLE-US-00017 TABLE 17 .sup.1H-NMR (measured at 400 MHz, 500 MHz, ESI MS (m/z) or Example Formula or 600 MHz) δ ppm IR (KBr) cm.sup.−1 1-41 [00084] 1.37 (6H, d), 4.59 (1H, sep), 6.76 (1H, dd), 7.08 (1H, dd), 7.28 (1H, t), 7.34 (1H, dd), 7.50 (1H, m), 8.19 (1H, br) m/z = 311 (M + H) 1-42 [00085] 1.28 (6H, d), 2.95 (1H, sep), 7.12 (1H, d), 7.34 (1H, t), 7.48 (2H, m), 7.51 (1H, m) m/z = 295 (M + H) 1-43 [00086] 3.96 (3H, s), 6.92 (1H, d), 7.32 (1H, d), 7.56 (1H, m) m/z = 317 (M + H) 1-44 [00087] 3.85 (3H, s), 6.79 (1H, m), 7.11 (1H, d), 7.29 (1H, t), 7.38 (1H, m), 7.51 (1H, m) m/z = 283 (M + H) 1-45 [00088] 7.35 (1H, t), 7.39 (1H, dd), 7.46 (1H, t), 7.54 (1H, m), 7.58 (1H, d), 7.93 (2H, m), 8.20 (1H, d), 8.50 (1H, br) m/z = 313 (M + H) 1-46 [00089] 2.40 (3H, s), 7.06 (1H, d), 7.30 (1H, t), 7.42 (1H, d), 7.47 (1H, m), 7.51 (1H, s) m/z = 267 (M + H) 1-47 [00090] 6.88 (1H, m), 7.05 (2H, m), 7.15 (1H, m), 7.36 (5H, m), 7.49 (1H, m), 8.20 (1H, br) m/z = 345 (M + H) 1-48 [00091] 7.47 (1H, m), 7.61 (1H, dd), 8.58 (1H, d), 9.04 (1H, d) m/z = 255 (M + H) 1-49 [00092] 7.43 (1H, dd), 7.52 (1H, m), 8.28 (1H, dd), 8.35 (1H, br), 8.50 (1H, m), 8.78 (1H, m) m/z = 254 (M + H) 1-50 [00093] 1.39 (9H, s), 6.89 (1H, m), 7.30 (2H, m), 7.39 (1H, m), 7.52 (1H, m) m/z = 325 (M + H)

TABLE-US-00018 TABLE 18 .sup.1H-NMR (measured at 400 MHz, 500 MHz, ESI MS (m/z) or Example Formula or 600 MHz) δ ppm IR (KBr) cm.sup.−1 1-51 [00094] 7.25-7.27 (m, 1H), 7.49 (m, 1H), 7.84 (m, 1H) m/z = 244 (M + H) 1-52 [00095] 7.11 (1H, d), 7.41-7.51 (3H, m), 7.71 (1H, s), 8.34 (1H br) m/z = 337 (M + H) 1-53 [00096] 7.23 (1H, m), 7.42 (1H, m), 7.50 (1H, m), 7.75 (1H, m), 8.27 (1H, br) m/z = 305 (M + H) 1-54 [00097] 7.38 (2H, d), 7.50 (1H, m), 7.60 (1H, d), 8.21 (1H, br) m/z = 287 (M + H) 1-55 [00098] 7.52 (1H, m), 7.72 (2H, d), 7.80 (2H, d), 8.37 (1H, br) m/z = 278 (M + H) 1-56 [00099] 1.41 (3H, t), 4.40 (2H, q), 7.52 (1H, m), 7.73 (2H, d), 8.10 (2H, d), 8.35 (1H, br) m/z = 325 (M + H) 1-57 [00100] 1.43 (3H, t), 4.05 (2H, q), 6.92 (2H, m), 7.52 (3H, m) m/z = 297 (M + H) 1-58 [00101] 2.31 (3H, s), 7.04 (1H, m), 7.39 (1H, m), 7.49 (2H, m), 8.16 (1H, br) m/z = 285 (M + H) 1-59 [00102] 1.34 (6H, d), 4.55 (1H, sep), 6.92 (2H, d), 7.53 (3H, m), 8.14 (1H, br) m/z = 311 (M + H) 1-60 [00103] 1.26 (6H, d), 2.93 (1H, sep), 7.28 (2H, d), 7.54 (3H, m) m/z = 295 (M + H)

TABLE-US-00019 TABLE 19 .sup.1H-NMR (measured at 400 MHz, 500 MHz, ESI MS (m/z) or Example Formula or 600 MHz) δ ppm IR (KBr) cm.sup.−1 1-61 [00104] 3.83 (3H, s), 6.94 (2H, d), 7.51 (1H, m), 7.54 (2H, d) m/z = 283 (M + H) 1-62 [00105] 3.93 (3H, s), 6.70 (1H, m), 7.45 (1H, m), 7.91 (1H, s), 8.14 (1H, d), 8.86 (1H, br) m/z = 284 (M + H) 1-63 [00106] 2.21 (1H, s), 3.88 (1H, s), 6.93 (1H, d), 7.13 (1H, d), 7.38 (1H, s), 7.51 (1H, m), 8.19 (1H, br) m/z = 297 (M + H) 1-64 [00107] 2.62 (3H, s), 7.40 (1H, d), 7.52 (1H, m), 7.81 (1H, dd), 8.32 (1H, d), 8.35 (1H, br) m/z = 312 (M + H) 1-65 [00108] 2.49 (3H, s), 7.34 (1H, d), 7.52 (1H, m), 7.75 (1H, dd), 7.85 (1H, d), 8.26 (1H, br) m/z = 335 (M + H) 1-66 [00109] 2.37 (3H, s), 7.21 (2H, d), 7.51 (3H, m), 8.17 (1H, br) m/z = 267 (M + H) 1-67 [00110] 7.53 (1H, m), 7.85 (2H, d), 8.31 (2H, d), 8.48 (1H, br) m/z = 298 (M + H) 1-68 [00111] 7.04 (4H, m), 7.13 (1H, m), 7.35 (2H, m), 7.52 (1H, m), 7.60 (2H, m) m/z = 345 (M + H) 1-69 [00112] 7.44 (1H, m), 7.70 (2H, d), 8.53 (2H, d), 10.36 (1H, br) m/z = 254 (M + H) 1-70 [00113] 1.36 (9H, s), 7.04 (2H, d), 7.53 (3H, m) m/z = 325 (M + H)

TABLE-US-00020 TABLE 20 .sup.1H-NMR (measured at 400 MHz, 500 MHz, ESI MS (m/z) or Example Formula or 600 MHz) δ ppm IR (KBr) cm.sup.−1 1-71 [00114] 1.33 (s, 9H), 7.42-7.56 (m, 5H), 8.15-8.23 (m, 1H) m/z = 309 (M + H) 1-72 [00115] 7.27 (2H, m), 7.51 (1H, m), 7.68 (2H, m), 8.26 (1H, br) m/z = 337 (M + H) 1-73 [00116] 2.47 (3H, s), 6.79 (1H, s), 7.46 (1H, m) m/z = 258 (M + H) 1-74 [00117] 2.46 (3H, s), 7.12 (1H, s), 7.48 (1H, m) m/z = 274 (M + H) 1-75 [00118] 4.68 (2H, d), 7.32-7.40 (5H, m), 7.46 (1H, m) m/z = 267 (M + H) 1-76 [00119] 1.48 (s, 9H), 6.39 (br s, 1H), 7.37 (t, J = 2.9 Hz, 1H) 1-77 [00120] 3.65-3.68 (m, 2H), 3.85-3.86 (m, 2H), 4.04 (s, 3H), 7.01 (t, J = 2.8 Hz, 1H), 7.09 (br s, 1H) 1-78 [00121] 1.92 (1H, br), 3.69 (2H, m), 3.87 (2H, br), 7.43 (1H, m) m/z = 221 (M + H) 1-79 [00122] 1.64 (bs, 1H), 2.79-2.84 (m, 2H), 3.67-3.72 (M, 2H), 7.05 (br s, 1H), 7.42-7.44 (m, 1H) 1-80 [00123] 4.68 (2H, d), 7.32-7.40 (5H, m), 7.46 (1H, m) m/z = 267 (M + H)

TABLE-US-00021 TABLE 21 .sup.1H-NMR (measured at 400 MHz, 500 MHz, ESI MS (m/z) or Example Formula or 600 MHz) δ ppm IR (KBr) cm.sup.−1 1-81 [00124] 4.00 (2H, m), 5.30 (1H, m), 7.33-7.43 (6H, m) IR 1654, 1542, 1466, 1437, 1383, 1053, 1030, 754 1-82 [00125] 1.29 (6H, d), 4.30 (1H, dsep), 6.40 (1H, br), 7.42 (1H, m) 1-83 [00126] 1.62 (3H, d), 5.53 (1H, m), 7.02 (1H, br), 7.27 (1H, dd), 7.30 (1H, d), 7.39 (1H, m), 7.42 (1H, d) m/z = 349 (M + H) 1-84 [00127] 1.63 (3H, d), 5.30 (1H, m), 6.81 (1H, br), 7.32 (2H, m), 7.37 (2H, m), 7.42 (1H, m) m/z = 315 (M + H) 1-85 [00128] 1.65 (3H, d), 5.34 (1H, m), 6.84 (1H, br), 7.31-7.44 (6H, m) m/z = 281 (M + H) 1-86 [00129] 3.81 (3H, s), 4.28 (2H, d), 7.42 (1H, m) IR 1747, 1655, 1553, 1466, 1428, 1383, 1218, 1032, 771 1-87 [00130] 3.60 (2H, m), 3.92 (2H, m), 7.12 (1H, br), 7.40 (1H, m) IR 3295, 1742, 1663, 1636, 1543, 1470, 1429, 1375, 1359, 1032, 1013 1-88 [00131] 1.00 (3H, t), 1.68 (2H, sext), 3.48 (2H, m), 7.43 (1H, m) m/z = 219 (M + H) 1-89 [00132] 1.43 (9H, s), 3.41 (2H, dd), 3.60 (2H, dd), 4.91 (1H, br), 7.36 (1H, s), 7.52 (1H, br) m/z = 320 (M + H) 1-90 [00133] 4.14 (2H, m), 5.25-5.32 (2H, m), 5.93 (1H, m), 6.67 (1H, br), 7.44 (1H, m) m/z = 217 (M + H)

TABLE-US-00022 TABLE 22 .sup.1H-NMR (measured at 400 MHz, 500 MHz, ESI MS (m/z) or Example Formula or 600 MHz) δ ppm IR (KBr) cm.sup.−1 1-91 [00134] 4.43 (2H, d), 6.99 (1H, br), 7.48 (1H, s) 1-92 [00135] 3.08 (3H, d), 6.65 (1H, br), 7.45 (1H, m) m/z = 191 (M + H) 1-93 [00136] 7.06 (1H, m), 7.61 (2H, m), 7.70 (1H, m), 8.10 (2H, m) IR 1712, 1634, 1465, 1453, 1375, 1197, 1167, 851, 541 1-94 [00137] 1.26 (3H, m), 1.43 (2H, m), 1.65 (1H, m), 1.77 (2H, m), 2.02 (2H, m), 4.00 (1H, m), 6.44 (1H, br), 7.42 (1H, m) m/z = 259 (M + H) 1-95 [00138] 0.68 (2H, m), 0.95 (2H, m), 2.95 (1H, m), 6.69 (1H, br), 7.44 (1H, m) m/z = 217 (M + H) 1-96 [00139] 0.88 (3H, t), 1.27-1.38 (10H, m), 1.64 (2H, m), 3.48 (2H, m), 6.95 (1H, br), 7.43 (1H, m) m/z = 289 (M + H) 1-97 [00140] 3.87 (3H, s), 7.40 (1H, m), 9.12 (1H, br) m/z = 207 (M + H) 1-98 [00141] 7.25 (1H, m), 7.42 (2H, m), 7.52 (1H, m), 7.64 (2H, d), 8.23 (1H br) m/z = 253 (M + H) 1-99 [00142] 4.57 (2H, s), 7.31 (4H, m), 7.39 (1H, s), 7.41 (1H, s), 7.48 (1H, d), 7.76 (1H, m), 7.85 (1H, s) m/z = 420 (M + H) 1-100 [00143] 5.53 (2H, s), 7.33 (3H, m), 7.44 (1H, d), 7.51 (1H, d) m/z = 302 (M + H)

TABLE-US-00023 TABLE 23 .sup.1H-NMR (measured at 400 MHz, 500 MHz, ESI MS (m/z) or Example Formula or 600 MHz) δ ppm IR (KBr) cm.sup.−1 1-101 [00144] 7.47-7.51 (3H, m), 7.74 (1H, dt), 7.77 (1H, dd) m/z = 279 (M + H) 1-102 [00145] 2.34 (s, 3H), 5.40 (s, 2H), 7.15 (d, J = 8.3 Hz, 1H), 7.25- 7.26 (m, 1H), 7.28-7.31 (m, 1H), 7.42-7.44 (m, 1H), 7.53- 7.54 (m, 1H) 1-103 [00146] 3.85 (3H, s), 7.02 (2H, m), 7.16 (1H, dd), 7.29 (1H, m), 7.45 (1H, m) m/z = 283 (M + H) 1-104 [00147] 5.61 (2H, s), 7.32 (1H, m) m/z = 341 (M + H) 1-105 [00148] 5.39 (2H, s), 7.29-7.37 (4H, m), 7.43 (1H, s) m/z = 302 (M + H) 1-106 [00149] 5.39 (2H, s), 7.28 (1H, m), 7.39 (4H, m) m/z = 302 (M + H) 1-107 [00150] 7.19 (2H, m), 7.44 (3H, m) m/z = 288 (M + H) 1-108 [00151] 7.43 (3H, m), 7.79 (2H, dd) m/z = 279 (M + H) 1-109 [00152] 3.82 (3H, s), 5.36 (2H, s), 6.93 (2H, d), 7.26 (1H, m), 7.38 (2H, d) m/z = 298 (M + H) 1-110 [00153] 2.36 (3H, s), 5.38 (2H, s), 7.21 (2H, d), 7.26 (1H, m), 7.33 (2H, d) m/z = 282 (M + H)

TABLE-US-00024 TABLE 24 .sup.1H-NMR (measured at 400 MHz, 500 MHz, ESI MS (m/z) or Example Formula or 600 MHz) δ ppm IR (KBr) cm.sup.−1 1-111 [00154] 2.39 (3H, s), 7.11 (2H, dd), 7.25 (2H, dd), 7.42 (1H, m) m/z = 268 (M + H) 1-112 [00155] 7.46 (3H, m), 8.37 (2H, m) m/z = 299 (M + H) 1-113 [00156] 2.24 (3H, s), 5.14 (2H, s), 7.29 (1H, m) IR 1825, 1746, 1634, 1474, 1365, 1230, 1031, 770 1-114 [00157] 5.41 (2H, s), 7.28 (1H, m), 7.37-7.46 (5H, m) m/z = 268 (M + H) 1-115 [00158] 1.57 (d, J = 6.9 Hz, 3H), 5.53- 5.58 (m, 1H), 7.29-7.30 (m, 1H) 1-116 [00159] 2.60-2.68 (m, 2H), 4.63 (t, J = 6.3 Hz, 2H), 7.27 (t, J = 2.8 Hz, 1H) 1-117 [00160] 1.43 (3H, t), 4.47 (2H, q), 7.27 (1H, m) m/z = 206 (M + H) 1-118 [00161] 1.40 (6H, d), 5.30 (1H, sep), 7.25 (1H, m) m/z = 220 (M + H) 1-119 [00162] 2.59 (1H, t), 4.99 (2H, d), 7.33 (1H, m) m/z = 216 (M + H) 1-120 [00163] 4.76-4.79 (m, 2H), 7.31-7.32 (m, 1H)

TABLE-US-00025 TABLE 25 .sup.1H-NMR (measured at 400 MHz, 500 MHz, ESI MS (m/z) or Example Formula or 600 MHz) δ ppm IR (KBr) cm.sup.−1 1-121 [00164] 1.03 (6H, d), 2.09 (1H, m), 4.19 (2H, d), 7.28 (1H, m) IR 1732, 1472, 1439, 1384, 1366, 1276, 1256, 1034, 992, 758 1-122 [00165] 4.99 (2H, d), 6.18 (1H, t), 7.29 (1H, m) IR 1740, 1437, 1439, 1387, 1361, 1250, 1207, 1035, 878 1-123 [00166] 1.03 (3H, t), 1.81 (2H, sext), 4.37 (2H, t), 7.28 (1H, m) m/z = 220 (M + H) 1-124 [00167] 5.06 (2H, d), 6.36 (1H, dt), 6.79 (1H, d), 7.29-7.34 (4H, m), 7.42 (2H, m) m/z = 294 (M + H) 1-125 [00168] 1.32 (3H, t), 4.28 (2H, q), 4.91 (2H, s), 7.35 (1H, m) m/z = 264 (M + H) 1-126 [00169] 4.01 (3H, s), 7.29 (1H, m), m/z = 192 (M + H) 1-127 [00170] 0.88 (3H, m), 1.27-1.39 (8H, m), 1.66 (2H, m), 1.77 (2H, m), 4.39 (2H, t), 7.28 (1H, m) m/z = 290 (M + H) 1-128 [00171] 4.90 (2H, d), 5.37 (1H, dd), 5.43 (1H, dd), 6.01 (1H, m), 7.30 (1H, m) m/z = 218 (M + H) 1-129 [00172] 7.24 (2H, d), 7.34 (1H, t), 7.43-7.48 (3H, m) m/z = 254 (M + H) 1-130 [00173] 7.22 (1H, m), 7.52 (5H, m) m/z = 270 (M + H)

TABLE-US-00026 TABLE 26 .sup.1H -NMR (measured at 400 MHz, 500 MHz, ESI MS (m/z) or Example Formula or 600 MHz) δ ppm IR (KBr) cm.sup.−1 1-131 [00174] 3.96 (3H, s), 6.95 (1H, dd), 7.04 (1H, td), 7.15 (1H, td), 8.46 (2H, m) m/z = 265 (M + H) 1-132 [00175] 3.81 (6H, S), 6.34 (1H, t), 6.84 (2H, s), 7.24 (2H, s), 7.67 (1H, br) m/z = 295 (M + H) 1-133 [00176] 2.37 (3H, s), 7.24 (2H, s), 7.37 (1H, m), 7.71 (2H, m) m/z = 283 (M + H) 1-134 [00177] 1.36 (6H, d), 4.58 (1H, tt), 6.76 (1H, m), 7.05 (1H, m), 7.27 (3H, m), 7.33 (1H, s), 7.74 (1H, br) m/z = 293 (M + H) 1-135 [00178] 3.84 (3H, s), 6.77 (1H, m), 7.10 (1H, m), 7.25 (2H, s), 7.30 (1H, t), 7.35 (1H, br), 7.77 (1H, br) m/z = 265 (M + H) 1-136 [00179] 1.25 (3H, t), 2.66 (2H, q), 7.22 (2H, s), 7.25 (2H, s), 7.51 (2H, d), 7.69 (1H, br) m/z = 263 (M + H) 1-137 [00180] 1.34 (6H, d), 4.54 (1H, m), 6.91 (2H, m), 7.24 (2H, s), 7.49 (2H, d), 7.66 (1H, s) m/z = 293 (M + H) 1-138 [00181] 3.83 (3H, s), 6.93 (2H, m), 7.25 (2H, d), 7.51 (2H, d), 7.69 (1H, br) m/z = 265 (M + H) 1-139 [00182] 7.27 (2H, s), 7.53 (2H, m), 7.85 (1H, d), 7.93 (2H, m) m/z = 303 (M + H) 1-140 [00183] 4.64 (2H, d), 6.36 (1H, br), 7.16 (2H, s), 7.28 (5H, m) m/z = 249 (M + H)

TABLE-US-00027 TABLE 27 .sup.1H-NMR (measured at 400 MHz, 500 MHz, ESI MS (m/z) or Example Formula or 600 MHz) δ ppm IR (KBr) cm.sup.−1 1-141 [00184] 1.61 (3H, d), 5.27 (1H, m), 6.26 (1H, br) 7.13 (2H, s), 7.33 (4H, m) m/z = 297 (M + H) 1-142 [00185] 1.00 (3H, t), 1.67 (2H, td), 3.44 (2H, q), 6.11 (1H, br), 7.14 (2H, s) m/z = 201 (M + H) 1-143 [00186] 7.21 (3H, m), 7.41 (2H, m), 7.61 (2H, d) m/z = 234 (M + H) 1-144 [00187] 2.95 (2H, t), 3.74 (2H, dd), 6.07 (1H, br), 7.03 (2H, s), 7.26 (3H, m), 7.37 (2H, m) m/z = 263 (M + H) 1-145 [00188] 2.32 (s, 3H), 5.38 (s, 2H), 7.15 (d, J = 8.2 Hz, 1H), 7.26- 7.37 (m, 3H), 7.44 (t, J = 7.7 Hz, 1H), 7.51 (d, J = 7.4 Hz, 1H) 1-146 [00189] 7.21-7.26 (m, 1H), 7.39-7.43 (m, 2H), 7.62-7.64 (m, 2H), 7.91-7.95 (m, 2H), 8.10 (s, 1H), 8.90-8.92 (m, 1H) 1-147 [00190] 1.44 (t, 3H), 4.47 (q, 2H), 8.06-8.07 (m, 1H), 8.23 (s, 1H), 8.90 (m, 1H) 1-148 [00191] 3.92-3.96 (m, 2H), 4.61-4.64 (m, 2H), 7.00 (br s, 1H), 7.30- 7.32 (m, 1H), 7.43 (s, 1H) 1-149 [00192] 7.52 (2H, m), 7.72 (4H, s) m/z = 427 (M + H) 1-150 [00193] 2.83 (2H, m), 3.69 (2H, m), 7.30 (2H, m), 8.06 (1H, br) m/z = 379 (M + H)

TABLE-US-00028 TABLE 28 .sup.1H-NMR (measured at 400 MHz, 500 MHz, ESI MS (m/z) or Example Formula or 600 MHz) δ ppm IR (KBr) cm.sup.−1 1-151 [00194] 5.10 (4H, d), 6.00 (2H, t), 7.31 (2H, m) m/z = 407 (M + H) 1-152 [00195] 4.97 (4H, d), 6.11 (2H, t), 7.32 (2H, m) m/z = 407 (M + H) 1-153 [00196] 7.25 (m, 2H), 7.36-7.40 (m, 2H), 7.57-7.59 (m, 2H), 7.72 (br s, 1H) m/z = 267 (M − H) 1-154 [00197] 7.16-7.27 (m, 5H), 7.97 (br s, 1H), 8.38 (t, J = 7.8 Hz, 1H) m/z = 251 (M − H) 1-155 [00198] 7.24 (m, 2H), 7.43-7.49 (m, 2H), 7.72 (br s, 1H), 7.88 (d, J = 2.1 Hz, 1H) m/z = 301 (M − H) 1-156 [00199] 1.33 (s, 9H), 7.25 (m, 2H), 7.41-7.44 (m, 2H), 7.52-7.54 (m, 2H), 7.69 (br s, 1H) m/z = 291 (M + H) 1-157 [00200] 1.31 (s, 9H), 7.17-7.23 (m, 4H), 7.89 (br s, 1H), 8.24 (t, J = 8.4 Hz, 1H) m/z = 309 (M + H) 1-158 [00201] 1.29 (d, J = 6.6 Hz, 6H), 4.23- 4.32 (m, 1H), 5.88 (br s, 1H), 7.13 (s, 2H) m/z = 201 (M + H) 1-159 [00202] 4.08-4.12 (m, 2H), 5.24-5.32 (m, 2H), 5.87-5.97 (m, 1H), 6.16 (br s, 1H), 7.16 (s, 2H) m/z = 199 (M + H) 1-160 [00203] 2.34 (t, J = 2.6 Hz, 1H), 4.26- 4.28 (m, 2H), 6.29 (br s, 1H), 7.17 (s, 2H) m/z = 197 (M + H)

TABLE-US-00029 TABLE 29 .sup.1H-NMR (measured at 400 MHz, 500 MHz, ESI MS (m/z) or Example Formula or 600 MHz) δ ppm IR (KBr) cm.sup.−1 1-161 [00204] 7.14-7.18 (m, 1H), 7.31 (m, 2H), 7.79-7.83 (m, 1H), 8.31- 8.34 (m, 2H), 8.54 (br s, 1H) m/z = 236 (M + H) 1-162 [00205] 5.64 (s, 2H), 7.50 (m, 2H), 7.52-7.56 (m, 2H), 7.64-7.69 (m, 1H), 7.94-7.97 (m, 2H) m/z = 278 (M + H) 1-163 [00206] 7.31-7.35 (m, 3H), 7.68-7.73 (m, 2H), 8.25 (br s, 1H), 8.50 (d, J = 8.4 Hz, 1H) m/z = 258 (M + H) 1-164 [00207] 7.13-7.14 (m, 1H), 7.53-7.56 (m, 2H), 7.66-7.68 (m, 1H), 7.87-7.89 (m, 2H), 9.33 (br s, 1H) 1-165 [00208] 2.41 (s, 3H), 7.31-7.36 (m, 2H), 7.50-7.52 (m, 1H), 7.83- 7.84 (m, 1H), 9.04 (br s, 1H) m/z = 315.01 (M − H) 1-166 [00209] 1.37 (d, J = 6.1 Hz, 6H), 4.55- 4.60 (m, 1H), 6.87-6.89 (m, 1H), 7.13-7.17 (m, 1H), 7.32- 7.36 (m, 2H), 7.57-7.58 (m, 1H), 9.06 (br s, 1H) m/z = 325.07 (M − H) 1-167 [00210] 7.50 (m, 3H), 7.82-7.84 (m, 1H), 7.96 (s, 1H), 8.31-8.33 (m, 1H) 1-168 [00211] 1.26 (3H, t), 2.68 (2H, q), 7.06- 7.08 (1H, m), 7.25-7.34 (3H, m), 7.42-7.46 (2H, m), 7.70 (1H, br s) m/z = 263 (M + H) 1-169 [00212] 1.29 (3H, t), 2.67 (2H, q), 7.22- 7.31 (5H, m), 7.83 (1H, br s), 7.83-7.84 (1H, m) m/z = 263 (M + H) 1-170 [00213] 2.36 (3H, s), 7.20-7.26 (4H, m), 7.48-7.52 (2H, m), 7.68 (1H, br s) m/z = 247 (M − H)

TABLE-US-00030 TABLE 30 .sup.1H-NMR (measured at 400 MHz, 500 MHz, ESI MS (m/z) or Example Formula or 600 MHz) δ ppm IR (KBr) cm.sup.−1 1-171 [00214] 7.26-7.28 (2H, m), 7.37-7.40 (1H, m), 7.91 (1H, br s), 8.24- 8.26 (1H, m), 8.47-8.48 (1H, m), 8.70-8.71 (1H, m) m/z = 234 (M − H) 1-172 [00215] 7.27 (2H, m), 7.59-7.61 (2H, m), 7.97 (1H, brs), 8.61-8.62 (2H, m) m/z = 234 (M − H) 1-173 [00216] 7.32-7.36 (3H, m), 7.76-7.80 (1H, m), 8.32-8.35 (1H, m), 8.91- 8.94 (1H, m), 11.43 (1H, br s) m/z = 278 (M − H) 1-174 [00217] 5.40 (2H, s), 7.26-7.41 (4H, m), 7.74-7.77 (1H, m), 8.50 (1H, m) m/z = 285 (M + H) 1-175 [00218] 7.65 (2H, m), 7.71-7.76 (1H, m), 8.07-8.10 (1H, m), 8.24-8.27 (1H, m), 8.83-8.85 (1H, m), 10.25 (1H, brs) m/z = 278 (M − H) 1-176 [00219] 7.64 (2H, s), 8.10-8.14 (2H, m), 8.31-8.35 (2H, m), 10.33 (1H, br s) m/z = 278 (M − H) 1-177 [00220] 1.29 (6H, d, J = 6.85 Hz), 3.01- 3.08 (1H, m), 7.26-7.32 (4H, m), 7.36-7.38 (1H, m), 7.68-7.70 (2H, m) m/z = 277 (M + H) 1-178 [00221] 1.27 (6H, d, J = 6.85 Hz), 2.90- 2.97 (1H, m), 7.09-7.11 (1H, d), 7.25-7.35 (3H, m), 7.45-7.46 (2H, m), 7.74 (1H, br s) m/z = 277 (M + H) 1-179 [00222] 1.26 (6H, d, J = 6.85 Hz), 2.89- 2.96 (1H, m), 7.24-7.27 (4H, m), 7.51-7.53 (2H, m), 7.74 (1H, br s) m/z = 277 (M + H) 1-180 [00223] 0.93 (3H, t, J = 7.34 Hz), 1.31-1.40 (2H, m), 1.56-1.64 (2H, m), 2.59- 2.64 (2H, m), 7.20-7.26 (4H, m), 7.50 (2H, d, J = 8.31 Hz), 7.74 (1H, br s) m/z = 291 (M + H)

TABLE-US-00031 TABLE 31 .sup.1H-NMR (measured at 400 MHz, 500 MHz, ESI MS (m/z) or Example Formula or 600 MHz) δ ppm IR (KBr) cm.sup.−1 1-181 [00224] 0.87-0.90 (3H, m), 1.26-1.37 (6H, m), 1.56-1.64 (2H, m), 2.59- 2.63 (2H, m), 7.20-7.26 (4H, m), 7.49-7.51 (2H, m), 7.73 (1H, br s) m/z = 319 (M + H) 1-182 [00225] 2.58 (1H, t), 4.98 (2H, d), 7.42- 7.43 (2H, m) m/z = 197 (M+) 1-183 [00226] 5.40 (2H, s), 7.38-7.44 (7H, m) m/z = 249 (M+) 1-184 [00227] 1.04 (3H, t), 1.77-1.86 (2H, m), 4.33-4.36 (2H, m), 7.38-7.39 (2H, m) m/z = 201 (M +) 1-185 [00228] 1.42 (3H, t), 4.44 (2H, q), 7.39 (2H, t) m/z = 187 (M+) 1-186 [00229] 1.27 (3H, t), 2.69 (2H, q), 7.10- 7.14 (2H, m), 7.26-7.29 (2H, m), 7.55 (2H, t) m/z = 263 (M+) 1-187 [00230] 3.83 (3H, s), 6.76-6.89 (3H, m), 7.34-7.38 (1H, m), 7.55 (2H, t) m/z = 265 (M+) 1-188 [00231] 4.86-4.88 (2H, m), 5.35-5.47 (2H, m), 5.97-6.07 (1H, m), 7.41 (2H, t) m/z = 199 (M+) 1-189 [00232] 3.99 (3H, s), 7.39 (2H, t) m/z = 173 (M+) 1-190 [00233] 2.51 (s, 3H), 7.08-7.14 (m, 1H), 7.26 (s, 1H), 7.32 (s, 2H), 7.59 (s, 1H), 7.74 (br. S., 1H) m/z = 277 (M + H)

TABLE-US-00032 TABLE 32 .sup.1H-NMR (measured at 400 MHz, 500 MHz, ESI MS (m/z) or Example Formula or 600 MHz) δ ppm IR (KBr) cm.sup.−1 1-191 [00234] 7.26-7.27 (s, 1H), 7.50-7.55 (m, 2H), 7.83-7.85 (d, 1H), 7.90 (s, 1H), 7.92 (s, 1H) m/z = 303 (M + H) 1-192 [00235] 6.59-6.60 (m, 3H), 11.47- 11.49 (m, 3H), 11.79 (m, 1H), 11.95 (m, 1H), 12.33 (m, 1H) m/z = 281 (M + H) 1-193 [00236] 6.65-6.73 (m, 1H), 7.05-7.12 (d, 1H), 7.20 (s, 2H), 7.31 (s, 1H) 7.36 (s, 2H), 8.88 (br. S., 1H), 9.52 (br. S, 1H) m/z = 251 (M + H) 1-194 [00237] m/z = 292 (M + H) 1-195 [00238] 7.38-7.40 (t, 1H), 7.47 (s, 4H), 7.50 (d, 1H), 7.52 (d, 1H), 8.26-8.27 (t, 1H) m/z = 391 (M + H) 1-196 [00239] 6.54-6.57 (m, 1H), 6.94-6.96 (m, 1H), 7.06-7.10 (t, 1H), 7.15-7.16 (t, 1H), 7.44 (s, 2H) m/z = 258 (M + H) 1-197 [00240] 7.50 (s, 2H), 7.65-7.67 (d, 1H), 7.93-7.96 (dd, 1H), 8.47- 8.48 (d, 1H) m/z = 312 (M − H) 1-198 [00241] 2.39 (3H, s), 7.08-7.11 (2H, m), 7.24-7.26 (2H, m), 7.55 (2H, t) m/z = 250 (M + H) 1-199 [00242] 7.16-7.20 (2H, m), 7.41-7.45 (2H, m), 7.54 (2H, t) m/z = 270 (M + H) 1-200 [00243] 3.84 (3H, s), 6.94-6.98 (2H, m), 7.13-7.16 (2H, m), 7.54 (2H, t) m/z = 265 (M+)

TABLE-US-00033 TABLE 33 .sup.1H-NMR (measured at 400 MHz, 500 MHz, ESI MS (m/z) or Example Formula or 600 MHz) δ ppm IR (KBr) cm.sup.−1 1-201 [00244] 7.12-7.22 (4H, m), 7.54 (2H, t) m/z = 253 (M+) 1-202 [00245] 7.38-7.40 (1H, m), 7.52-7.59 (3H, m), 7.68 (2H, m), 7.82- 7.95 (3H, m) m/z = 285 (M+) 1-203 [00246] 6.89-6.93 (1H, m), 7.48-7.57 (3H, m), 8.18-8.20 (1H, m), 8.35-8.39 (1H, m) m/z = 280 (M+) 1-204 [00247] 7.38-7.41 (2H, m), 7.54-7.57 (2H, m), 7.77-7.81 (2H, m) m/z = 260 (M+) 1-205 [00248] 1.37-1.64 (6H, m), 1.78-1.81 (2H, m), 1.94-1.99 (2H, m), 5.03-5.09 (1H, m), 7.38 (2H, m) m/z = 241 (M+) 1-206 [00249] 2.41 (3H, s), 7.00-7.08 (2H, m), 7.13-7.15 (1H, m), 7.32-7.36 (1H, m), 7.55 (2H, t) m/z = 249 (M+) 1-207 [00250] 6.99-7.09 (3H, m), 7.40-7.46 (1H, m), 7.54 (2H, t) m/z = 253 (M+) 1-208 [00251] 2.23 (3H, s), 7.12-7.14 (1H, m), 7.22-7.32 (3H, m), 7.57 (2H, t) m/z = 249 (M+) 1-209 [00252] 7.28-7.7.40 (3H, m), 7.51-7.54 (1H, m), 7.59 (2H, t) m/z = 269 (M+) 1-210 [00253] 3.83 (3H, s), 6.99-7.05 (2H, m), 7.14-7.16 (1H, m), 7.27-7.32 (1H, m), 7.56 (2H, m) m/z = 265 (M+)

TABLE-US-00034 TABLE 34 .sup.1H-NMR (measured at 400 MHz, 500 MHz, ESI MS (m/z) or Example Formula or 600 MHz) δ ppm IR (KBr) cm.sup.−1 1-211 [00254] 7.20-7.35 (4H, m), 7.57 (2H, m) m/z = 253 (M+) 1-212 [00255] 7.13-7.16 (1H, m), 7.26-7.42 (3H, m), 7.54 (2H, t) m/z = 269 (M+) 1-213 [00256] 0.89-0.93 (3H, m), 1.26-1.47 (6H, m), 1.74-1.81 (2H, m), 4.37 (2H, t), 7.38 (2H, s) m/z = 243 (M+) 1-214 [00257] 0.88 (3H, t), 1.26-1.46 (18H, m), 1.74-1.81 (2H, m), 4.37 (2H, t), 7.38 (2H, m) m/z = 327 (M+) 1-215 [00258] 3.09 (2H, t), 4.59 (2H, t), 7.25- 7.34 (6H, m), 7.36 (2H, m), m/z = 244 (M − F) 1-216 [00259] 5.02-5.04 (2H, m), 6.33-6.41 (1H, m), 6.77 (1H, d), 7.27-7.44 (7H, m) m/z = 275 (M+) 1-217 [00260] 1.29-1.36 (6H, m), 4.51-4.57 (1H, m), 6.91-6.95 (2H, m), 7.09-7.13 (2H, m), 7.54 (2H, t) m/z = 293 (M+) 1-218 [00261] 7.21-7.24 (2H, m), 7.31-7.36 (1H, m), 7.44-7.49 (2H, m), 7.56 (2H, m) m/z = 234 (M − H)

[0362] The compounds of Examples 2-1 to 2-5, represented by formula (3′), are shown in Table 35.

##STR00262##

TABLE-US-00035 TABLE 35 .sup.1H-NMR (measured at 400 MHz, 500 MHz, ESI MS (m/z) or Example Formula or 600 MHz) δ ppm IR (KBr) cm.sup.−1 2-1 [00263] 1.70 (6H, m), 3.26 (2H, m), 3.73 (2H, m), 6.82 (1H, m) m/z = 245 (M + H) 2-2 [00264] 4.07 (3H, s), 6.21 (1H, dd), 6.65 (1H, dd), 6.91 (1H, m), 7.04 (1H, m) IR 1638, 1630, 1467, 1155, 1023, 803, 7.53 2-3 [00265] 3.35 (2H, m), 3.70 (2H, m), 3.81 (4H, m), 6.86 (1H, m) m/z = 247 (M + H) 2-4 [00266] 3.22 (t, J = 8.3 Hz, 2H), 3.94 (t, J = 8.3 Hz, 2H), 6.91-6.93 (m, 1H), 7.16-7.18 (m, 1H), 7.25-7.30 (m, 2H), 8.25 (d, J = 8.2 Hz, 1H) 2-5 [00267] 7.84-7.95 (m, 4H), 8.05- 8.07 (m, 1H)

[0363] The compounds of Examples 3-1 and 3-2, represented by formula (4′), are shown in Table 36.

##STR00268##

TABLE-US-00036 TABLE 36 .sup.1H-NMR (measured at 400 MHz, 500 MHz, ESI MS (m/z) or Example Formula or 600 MHz) δ ppm IR (KBr) cm.sup.−1 3-1 [00269] 2.23 (3H, s), 5.24 (2H, s), 6.85 (1H, m) 3-2 [00270] 4.89 (2H, s), 7.05 (1H, m) IR 1641, 1480, 1455, 1430, 1364, 1268, 1206, 1154, 1088, 1023, 972, 878, 805

[0364] The compounds of Examples 4-1 to 4-4, represented by formula (5′), are shown in Table 37.

##STR00271##

TABLE-US-00037 TABLE 37 .sup.1H-NMR (measured at 400 MHz, 500 MHz, ESI MS (m/z) or Example Formula or 600 MHz) δ ppm IR (KBr) cm.sup.−1 4-1 [00272] 1.29 (3H, s), 3.35 (1H, m), 3.74 (1H, m), 4.07 (1H, m), 7.42 (1H, m) m/z = 217 (M + H) 4-2 [00273] 4.12 (2H, t), 4.53 (2H, t), 7.41 (1H, m) IR 1665, 1636, 1472, 1436, 1274, 1030, 996 4-3 [00274] 2.02 (2H, m), 3.65 (2H, m), 4.38 (2H, m), 7.24 (1H, m) IR 1654, 1635, 1472, 1431, 1374, 1248, 1133, 1078, 1027, 957, 761 4-4 [00275] 4.13 (2H, t), 4.50 (2H, t), 7.33 (2H, s) m/z = 185 (M + H)

Example 9

<Activity Against Rice Blast Disease>

[0365] The acetone solution of each compound of each example was prepared such that the content thereof became 0.1 mg/mL, and then diluted to 10-fold with water to be subjected to conduct test. 0.25 mL of the diluted solution per 1 mL of the soil was made to be absorbed in the soil. Rice seeds (cultivar: Jikkoku) subjected to forcing to germination were seeded in the soil to be cultivated in plant cultivation chambers. To the rice cultivated to the second leaf stage, the conidia suspension of Pyricularia oryzae prepared such that the content thereof became 1.5×10.sup.5 conidia spores/mL to 5×10.sup.5 conidia spores/mL was inoculated by conducting spraying, and then left still for 24 hours in a moist chamber (in which the temperature was 25° C. and the humidity was 100%). Then, the rice was continued to be cultivated in the plant cultivation chambers, and the number of lesions at the second leaf was counted. The control value was calculated based on the counted number of the lesions in accordance with the below-mentioned mathematical formula.

Control value=((the number of lesions at untreated plants−the number of lesions at treated plants)/the number of lesions at untreated plants)×100

[0366] The control values of the compounds of the below-mentioned examples were 80 or more, and control effects against the rice blast disease were confirmed.

[0367] 1-1, 1-2, 1-3, 1-4, 1-5, 1-7, 1-9, 1-12, 1-14, 1-15, 1-16, 1-17, 1-18, 1-19, 1-20, 1-21, 1-22, 1-24, 1-25, 1-26, 1-27, 1-28, 1-29, 1-30, 1-32, 1-33, 1-35, 1-36, 1-37, 1-39, 1-40, 1-44, 1-46, 1-47, 1-48, 1-50, 1-51, 1-52, 1-54, 1-55, 1-56, 1-57, 1-58, 1-59, 1-61, 1-63, 1-64, 1-65, 1-66, 1-67, 1-68, 1-70, 1-71, 1-73, 1-74, 1-78, 1-79, 1-80, 1-81, 1-84, 1-85, 1-86, 1-87, 1-88, 1-91, 1-92, 1-93, 1-96, 1-98, 1-99, 1-100, 1-102, 1-103, 1-104, 1-105, 1-107, 1-108, 1-109, 1-110, 1-111, 1-112, 1-114, 1-115, 1-117, 1-118, 1-119, 1-120, 1-122, 1-123, 1-124, 1-125, 1-127, 1-130, 1-132, 1-133, 1-134, 1-135, 1-137, 1-138, 1-139, 1-140, 1-141, 1-143, 1-145, 1-146, 1-147, 1-151, 1-152, 1-153, 1-155, 1-159, 1-168, 1-169, 1-170, 1-173, 1-174, 1-175, 1-176, 1-178, 1-179, 1-180, 1-181, 1-182, 1-183, 1-184, 1-185, 1-186, 1-187, 1-188, 1-189, 1-190, 1-191, 1-192, 1-193, 1-194, 1-196, 1-197, 1-198, 1-199, 1-200, 1-201, 1-202, 1-203, 1-204, 1-205, 1-206, 1-207, 1-208, 1-209, 1-210, 1-211, 1-213, 1-214, 1-218, 2-2, 2-4, 2-5, 3-1, 4-2, 4-3, 4-4

Example 10

<Activity Against Rice Blast Disease>

[0368] The acetone solution of each compound of each example was prepared at an approximate concentration, and then diluted to 10-fold with water, followed by adding 1/1000-fold by volume of NEOESTERIN to the diluted solution to be subjected to conducting test. Each of the compounds was sprayed onto rice cultivated in pots to the second leaf stage or the third leaf stage, and then, one day after conducting spraying, the conidia suspension of Pyricularia oryzae prepared such that the content thereof became 1.5×10.sup.5 conidia spores/mL to 5×10.sup.5 conidia spores/mL was inoculated by conducting spraying, followed by leaving the rice still for 24 hours in a moist chamber (in which the temperature was 25° C. and the humidity was 100%). Then, the rice was cultivated in plant cultivation chambers, and the number of lesions at the second leaf was counted. The control value was calculated based on the counted number of the lesions in accordance with the below-mentioned mathematical formula.

Control value=((the number of lesions at untreated plants−the number of lesions at treated plants)/the number of lesions at untreated plants)×100

[0369] The control values of the compounds of the below-mentioned examples were 80 or more at the concentration of 25 ppm, and control effects against the rice blast disease were confirmed.

[0370] 1-19, 1-30, 1-38, 1-41, 1-44, 1-59, 1-134, 1-135, 1-139, 1-168, 1-172, 1-174

[0371] The control values of the compounds of the below-mentioned examples were 80 or more at the concentration of 200 ppm, and control effects against the rice blast disease were confirmed.

[0372] 1-3, 1-18, 1-32, 1-33, 1-86, 1-93, 1-98, 1-102, 1-103, 1-105, 1-129, 1-131, 1-132, 1-133, 1-134, 1-135, 1-137, 1-138, 1-139, 1-168, 1-169, 1-170, 1-172, 1-173, 1-174, 1-175, 1-176, 1-177, 1-178, 1-179, 1-180, 1-183, 1-187, 1-190, 1-191, 1-193, 1-200, 1-202, 1-204, 1-210, 4-4

Example 11

<Activity Against Rice Bacterial Leaf Blight>

[0373] The acetone solution of each compound of each example was prepared such that the content thereof became 2 mg/mL, and then diluted to 10-fold with water, followed by adding 1/1000-fold by volume of NEOESTERIN to the diluted solution to be subjected to conducting test. Each of the compounds was sprayed onto rice cultivated in pots to the tillering stage, and then, three days after conducting spraying, Xanthomonas oryzae pv.oryzae was inoculated by leaving a scratch using needle tweezers. The rice was left still overnight in a moist chamber (in which the temperature was 21° C. and the humidity was 100%), and then cultivated in a greenhouse to measure the length of lesions (lesion length), 11 days after the inoculation. The control value was calculated based on an average of the measured lesion length in accordance with the below-mentioned mathematical formula.

Control value=((the lesion length at untreated plant−the lesion length at treated plant)/the lesion length at untreated plant)×100

[0374] The control values of the below-mentioned compounds were 50 or more at the concentration of 200 ppm, and control effects against the rice bacterial leaf blight were confirmed.

[0375] 1-134, 1-135, 1-136, 1-161

Example 12

<Activity Against Barley Powdery Mildew>

[0376] The acetone solution of each compound of each example was prepared such that the content thereof became 2 mg/mL, and then diluted to 10-fold with water, followed by adding 1/1000-fold by volume of NEOESTERIN to the diluted solution to be subjected to conducting test. Each of the compounds was sprayed onto two-row barley cultivated in small bats (30 cm×20 cm) for approximately one month after seeding, and then, 7 days after conducting spraying, the two-row barley was left in a greenhouse under conditions in which natural infection of Erysiphe graminis was allowed, followed by cultivating the two-row barley for approximately 1 month under the conditions in which continuous infection thereof was allowed. The number of lesions at the flag leaf on the main stem was counted, and the control value was calculated based on the counted number of lesions in accordance with the below-mentioned mathematical formula.

Control value=((the number of lesions at untreated plants−the number of lesions at treated plants)/the number of lesions at untreated plants)×100

[0377] The control values of the below-mentioned compounds were 50 or more at the concentration of 200 ppm, and control effects against the barley powdery mildew were confirmed.

[0378] 1-41, 1-134, 1-135

Example 13

<Activity Against Wheat Powdery Mildew>

[0379] Wettable powders of example compounds 1-134 and 1-135 were prepared in accordance with the below-mentioned Preparation Example 1, respectively, followed by diluting the wettable powders to 1000-fold with water to prepare spraying liquids. The prepared spraying liquids were sprayed onto wheat twice at the blooming stage and 10 days prior to the blooming stage at a liquid volume of 1 L/m.sup.2, respectively. The lesions on the flag leaf were examined in accordance with the below-mentioned indexes approximately 4 weeks after the second spraying application. The severity was calculated based on the indexes, and the control value was calculated from the obtained severity in accordance with the below-mentioned mathematical formula.

[0380] Indexes (0 to 5)

[0381] 0: No lesions were observed.

[0382] 1: 1 to 3 lesions were observed.

[0383] 2: 4 to 10 lesions were observed.

[0384] 3: 11 to 20 lesions were observed.

[0385] 4: 21 or more lesions were observed, and the area of lesions was less than half of the leaf surface.

[0386] 5: 21 or more lesions were observed, and the area of lesions was half or more of the leaf surface.

Control value=((the severity at untreated plants−the severity at treated plants)/the severity at untreated plants)×100

[0387] The control values of the example compounds 1-134 and 1-135 were 50 or more, and control effects were confirmed.

Example 14

<Activity Against Wheat Brown Rust>

[0388] Wettable powders of the example compound 1-135 were prepared in accordance with the below-mentioned Preparation Example 1, followed by diluting the wettable powders to 1000-fold with water to prepare spraying liquids. The prepared spraying liquid was sprayed onto wheat twice at the blooming stage and 10 days prior to the blooming stage at a liquid volume of 1 L/m.sup.2. The lesions on the flag leaf were examined in accordance with the below-mentioned indexes approximately 4 weeks after the second spraying application. The severity was calculated based on the indexes, and the control value was calculated from the obtained severity in accordance with the below-mentioned mathematical formula.

[0389] Indexes (0 to 5)

[0390] 0: No lesions were observed.

[0391] 1: 1 to 3 lesions were observed.

[0392] 2: 4 to 10 lesions were observed.

[0393] 3: 11 to 20 lesions were observed.

[0394] 4: 21 or more lesions were observed, and the area of lesions was less than half of the leaf surface.

[0395] 5: 21 or more lesions were confirmed, and the area of lesions was half or more of the leaf surface.

Control value=((the severity at untreated plants−the severity at treated plants)/the severity at untreated plants)×100

[0396] The control value of the example compound 1-135 was 50 or more, and control effects against the wheat brown rust were confirmed.

Example 15

<Activity Against Cucumber Downy Mildew>

[0397] The acetone solution of each example compound was prepared such that the content thereof became 0.4 mg/mL, and then diluted to 10-fold with water to be subjected to conducting test. 5 mL of the diluted solution was made to be absorbed in the soil per pot at the root of cucumber (cultivar: Suyo) cultivated to the first-leaf stage in the pot. 7 days after the treatment, the spore suspension of Pseudoperonospora cubensis prepared such that the content thereof became 5×10.sup.4 spores/mL was inoculated to the cucumber by conducting spraying, followed by leaving the cucumber still for 24 hours in a moist chamber (in which the temperature was 25° C. and the humidity was 100%). Then, the cucumber was cultivated in a greenhouse, and, 7 days after the inoculation, the lesions at the second leaf were examined in accordance with the below-mentioned indexes. The severity was calculated based on the indexes, and the control value was calculated from the obtained severity in accordance with the below-mentioned mathematical formula.

[0398] Indexes (0 to 5)

[0399] 0: No lesions were observed.

[0400] 1: The area of lesions was less than 5% of the leaf surface.

[0401] 2: The area of lesions was 5% or more but less than 25% of the leaf surface.

[0402] 3: The area of lesions was 25% or more but less than 50% of the leaf surface.

[0403] 4: The area of lesions was 50% or more but less than 80% of the leaf surface.

[0404] 5: The area of lesions was 80% or more of the leaf surface.

Control value=((the severity at untreated plants−the severity at treated plants)/the severity at untreated plants)×100

[0405] The control values of the below-mentioned compounds were 70 or more, and control effects against the cucumber downy mildew were confirmed.

[0406] 1-117, 1-134, 1-135, 1-143, 1-218, 4-2

Example 16

<Activity Against Cucumber Downy Mildew>

[0407] The acetone solution of each example compound was prepared such that the content thereof became 1 mg/mL, and then diluted to 10-fold with water to be subjected to conducting test. 1 mL of the diluted solution per pot was sprayed onto cucumber (cultivar: Suyo) cultivated to the first-leaf stage in pots. 7 days after the spraying application, the spore suspension of Pseudoperonospora cubensis prepared such that the content thereof became 5×10.sup.4 spores/mL was inoculated to the cucumber by conducting spraying, followed by leaving the cucumber still for 24 hours in a moist chamber (in which the temperature was 25° C. and the humidity was 100%). Then, the cucumber was cultivated in a greenhouse, and, 7 days after the inoculation, the area ratio of lesions at the second leaf was examined in accordance with the below-mentioned indexes. The severity was calculated based on the indexes, and the control value was calculated from the obtained severity in accordance with the below-mentioned mathematical formula.

[0408] Indexes (0 to 5)

[0409] 0: No lesions were observed.

[0410] 1: The area of lesions was less than 5% of the leaf surface.

[0411] 2: The area of lesions was 5% or more but less than 25% of the leaf surface.

[0412] 3: The area of lesions was 25% or more but less than 50% of the leaf surface.

[0413] 4: The area of lesions was 50% or more but less than 80% of the leaf surface.

[0414] 5: The area of lesions was 80% or more of the leaf surface.

Control value=((the severity at untreated plans−the severity at treated plants)/the severity at untreated plants)×100

[0415] The control values of the below-mentioned compounds were 70 or more, and control effects against the cucumber downy mildew were confirmed.

[0416] 1-143, 1-218

Example 17

<Activity Against Cucumber Bacterial Spot Disease>

[0417] Wettable powders of the example compound 1-134 were prepared in accordance with the below-mentioned Preparation Example 1. The wettable powders were diluted to 6666-fold with water, and then 20 mL of the diluted solution per pot was applied to cucumber (cultivar: Natsusuzumi) cultivated to the third leaf stage in pots by making the diluted solution to be absorbed in the soil, and then the cucumber was subjected to settled planting. 28 days after the settled planting, the number of lesions formed at the.sub.11th true leaves to the 20.sup.th true leaves were counted. The control value was calculated from the obtained number of lesions in accordance with the below-mentioned mathematical formula.

Control value=((the number of lesions at untreated plants−the number of lesions at treated plants)/the number of lesions at untreated plants)×100

[0418] The control value of the example compound 1-134 was 60 or more, and control effects thereof were confirmed.

Example 18

<Barrier to Growth of Rice>

[0419] The acetone solutions of each example compound and compounds described in the prior art documents shown in the below-mentioned Table 38 (hereinafter, referred to as compounds of Comparative Examples 1 to 5, respectively) were prepared such that the content thereof became 0.2 mg/mL, and then diluted to 10-fold with water to be subjected to conducting test. 0.25 mL of the diluted solution per 1 mL of the soil was made to be absorbed in the soil. Then, rice seeds (cultivar: Jikkoku) subjected to forcing to germination were seeded in the soil to be cultivated in plant cultivation chambers. The plant length of the rice grown to the first leaf stage was measured, and the ratio of the plant length, relative to the untreated plant length set as 100, (hereinafter, referred to as “the ratio of plant length relative to untreated plant length”) was calculated. The presence or absence of the barrier to growth was determined from the calculated ratio.

[0420] The ratios of plant length relative to untreated plant length of the below-mentioned example compounds were 80 or more, and it was confirmed that phytotoxicity caused thereby was reduced in comparison with the compounds of Comparative Examples 1 to 5. The results indicated that the damage caused by the below-mentioned example compounds was reduced in comparison with the compounds of formula (1) in which X.sup.1, X.sup.2, X.sup.3 or X.sub.4 contains a chlorine atom.

[0421] 1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 1-8, 1-9, 1-10, 1-11, 1-12, 1-13, 1-14, 1-15, 1-16, 1-17, 1-18, 1-19, 1-20, 1-21, 1-22, 1-23, 1-24, 1-25, 1-26, 1-27, 1-28, 1-29, 1-30, 1-31, 1-32, 1-33, 1-34, 1-35, 1-36, 1-37, 1-38, 1-39, 1-40, 1-41, 1-42, 1-43, 1-44, 1-45, 1-46, 1-47, 1-48, 1-49, 1-51, 1-52, 1-53, 1-54, 1-55, 1-56, 1-57, 1-58, 1-59, 1-60, 1-61, 1-62, 1-63, 1-64, 1-65, 1-66, 1-67, 1-68, 1-69, 1-70, 1-71, 1-72, 1-73, 1-74, 1-75, 1-76, 1-77, 1-78, 1-79, 1-80, 1-81, 1-82, 1-83, 1-84, 1-85, 1-86, 1-87, 1-88, 1-89, 1-90, 1-91, 1-92, 1-93, 1-95, 1-96, 1-97, 1-98, 1-99, 1-100, 1-101, 1-102, 1-103, 1-104, 1-105, 1-106, 1-107, 1-108, 1-109, 1-110, 1-111, 1-112, 1-113, 1-116, 1-117, 1-118, 1-120, 1-121, 1-122, 1-123, 1-124, 1-125, 1-126, 1-127, 1-128, 1-130, 1-131, 1-132, 1-133, 1-134, 1-135, 1-136, 1-137, 1-138, 1-139, 1-141, 1-142, 1-143, 1-148, 1-149, 1-150, 1-151, 1-152, 1-155, 1-156, 1-158, 1-160, 1-161, 1-164, 1-165, 1-166, 1-167, 1-168, 1-169, 1-170, 1-171, 1-172, 1-173, 1-174, 1-175, 1-176, 1-177, 1-178, 1-179, 1-180, 1-181, 1-182, 1-183, 1-184, 1-185, 1-186, 1-187, 1-188, 1-189, 1-190, 1-191, 1-192, 1-193, 1-194, 1-195, 1-196, 1-197, 1-198, 1-199, 1-200, 1-201, 1-202, 1-203, 1-204, 1-205, 2-1, 2-2, 2-3, 2-4, 2-5, 3-1, 3-2, 4-1, 4-2, 4-3, 4-4, 4-5

TABLE-US-00038 TABLE 38 Ratio of plant length relative to untreated Patent Compound plant Document Number Formula length Comparative Example 1 Japancese Unexamined Patent Application, First Publication No. Sho 63-93766 4.2 [00276] 49 Comparative Example 2 Japancese Unexamined Patent Application, First Publication No. Sho 63-93766 1.29 [00277] 52 Comparative Example 3 Japanese Unexamined Patent Application, First Publication No. Hei 9-165374 1 [00278] 45 Comparative Example 4 Japanese Unexamined Patent Application, First Publication No. Hei 10-95772 1 [00279] 64 Comparative Example 5 International Patent Application, Publication No. 2005-68430 I-1 [00280] 66

Preparation Example 1

[0422] 10 parts by mass of each example compound, 2 parts by mass of lauryl sulfate, 2 parts by mass of polyoxyethylene alkyl ether, 3 parts by mass of lignin sulfonate, 4 parts by mass of white carbon, and 79 parts by mass of clay were mixed and pulverized to obtain each wettable powder.

INDUSTRIAL APPLICABILITY

[0423] According to the present invention, a plant disease control agent and a novel compound that can reduce plant damage, and a method for controlling plant disease are provided. The plant disease control agent and the novel compound according to the present invention have excellent resistance-inducing activity and are useful to control plant diseases.