WO2010134634A1 - Amide compound and use thereof for control of plant diseases - Google Patents

Abstract

An amide compound represented by formula (1) [wherein R¹ represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, or the like; R² and R³ are as defined in the description; and p represents an integer of 1 to 5] or a salt thereof, which has an excellent plant disease control effect.

Description

Amide compounds and their plant disease control applications

The present invention relates to an amide compound and its use for controlling plant diseases.

Conventionally, many compounds have been developed and used for controlling plant diseases.

An object of the present invention is to provide a compound having an excellent plant disease control effect.
As a result of intensive studies to find a compound having an excellent plant disease control effect, the present inventors have found that the amide compound represented by the following formula (1) has an excellent plant disease control effect and completed the present invention. did. That is, the present invention is as follows.
[1] Formula (1)

[Where,
R ¹ is hydrogen, halogen, cyano group, nitro group, —O—R ⁴ group, —S—R ⁴ group, —S (═O) —R ⁴ group, —S (═O) ₂ —R ⁴ group, Represents a C1-C5 chain hydrocarbon group or C3-C5 cycloalkyl group optionally substituted with one or more groups selected from group B;
p represents any integer from 1 to 5;
R ² is a C1-C5 chain hydrocarbon group which may be substituted with one or more groups selected from group C, and a C3-C10 cycloalkyl group which may be substituted with one or more groups selected from group D , Phenyl group, halogen, cyano group, nitro group, —O—R ⁵ group, —S—R ⁵ group, —C (═O) —R optionally substituted with one or more groups selected from group E ⁵ groups, —C (═O) —OR ⁵ groups, —OC (═O) —R ⁵ groups, —NR ⁵ R ⁶ groups, —C (═O) —NR ⁵ R ⁶ groups or —NR ⁵ —C (= O) —R ⁶ group is represented,
Alternatively, when p is 2 or more and two R ² are bonded to adjacent carbons of the benzene ring, the two R ² are bonded and substituted with one or more groups selected from group E. An optionally substituted C2-C5 polymethylene group, a propene-1,3-diyl group optionally substituted with one or more groups selected from group E, and one or more groups selected from group E. Represents a 1,3-butadiene-1,4-diyl group or a methylenedioxy group,
R ³ is a C1-C5 chain hydrocarbon group which may be substituted with one or more groups selected from group C or a C3-C10 cycloalkyl group which may be substituted with one or more groups selected from group D Represents
R ⁴ represents a C1-C4 chain hydrocarbon group,
R ⁵ and R ⁶ are the same or different from each other, and are hydrogen, a C1 to C10 chain hydrocarbon group optionally substituted with one or more groups selected from group C, and one or more groups selected from group D. A C3-C10 cycloalkyl group which may be substituted or a phenyl group which may be substituted with one or more groups selected from group E.
However, when p is any integer of 2 to 5, R ² is the same or different from each other.
Group B represents a group consisting of halogen, cyano group, C1-C4 alkoxy group, C1-C4 alkylthio group, C1-C4 alkylsulfinyl group and C1-C4 alkylsulfonyl group,
Group C is a C3-C10 cycloalkyl group optionally substituted with one or more groups selected from Group D, a halogen, a cyano group, a C1-C4 alkoxy group optionally substituted with halogen, and a halogen-substituted group An optionally substituted C1-C4 alkylthio group, an optionally substituted C1-C4 alkylsulfinyl group, an optionally substituted C1-C4 alkylsulfonyl group, optionally substituted with a halogen (C1- C4 alkyl) represents a group consisting of a carbonyl group, a (C1-C4 alkoxy) carbonyl group optionally substituted with halogen, and a (C1-C4 alkyl) carbonyloxy group optionally substituted with halogen,
Group D represents a group consisting of a C1-C5 alkyl group and halogen,
Group E is halogen, cyano group, nitro group, C1-C10 chain hydrocarbon group optionally substituted with halogen, C3-C10 cycloalkyl group optionally substituted with one or more groups selected from group D C1-C4 alkoxy group optionally substituted with halogen, C1-C4 alkylthio group optionally substituted with halogen, C1-C4 alkylsulfinyl group optionally substituted with halogen, halogen-substituted May be a C1-C4 alkylsulfonyl group, a (C1-C4 alkyl) carbonyl group optionally substituted with halogen, a (C1-C4 alkoxy) carbonyl group optionally substituted with halogen, and a halogen-substituted Represents a group of good (C1-C4 alkyl) carbonyloxy groups. ]
Or an salt thereof.
[2] The amide compound or a salt thereof according to [1], wherein R ² is halogen.
[3] The amide compound or a salt thereof according to [1], wherein R ² is fluorine or chlorine.
[4] The amide compound or a salt thereof according to [1], wherein R ² is fluorine or bromine.
[5] The amide compound or a salt thereof according to [1], wherein p is 3, and R ² are the same or different from each other and are halogen.
[6] The amide compound or a salt thereof according to [1], wherein p is 3, and R ² are the same or different from each other and are fluorine or chlorine.
[7] The amide compound or a salt thereof according to [1], wherein p is 3, and R ² are the same or different from each other and are fluorine or bromine.
[8] A plant disease control agent comprising the amide compound or salt thereof according to any one of [1] to [7] and an inert carrier.
[9] A method for controlling plant diseases comprising a step of applying an effective amount of the amide compound or salt thereof according to any one of [1] to [7] to a plant or a soil in which the plant grows.
[10] Use of the amide compound or salt thereof according to any one of [1] to [7] for controlling plant diseases.

Various substituents used in the description of the present specification will be described below with examples.
“Halogen” means fluorine, chlorine, bromine and iodine.
Examples of the “C1-C5 chain hydrocarbon group optionally substituted with one or more groups selected from group B” include, for example, fluoromethyl group, difluoromethyl group, trifluoromethyl group, chloromethyl group, dichloromethyl group , Trichloromethyl group, bromomethyl group, dibromomethyl group, iodomethyl group, chlorodifluoromethyl group,
Ethyl group, 2-fluoroethyl group, 2,2,2-trifluoroethyl group, perfluoroethyl group, 2-chloroethyl group, 2,2,2-trichloroethyl group, 2-bromoethyl group, 2-iodoethyl group,
Propyl group, 3-fluoropropyl group, 3,3,3-trifluoropropyl group, perfluoropropyl group, 3-chloropropyl group, 3,3,3-trichloropropyl group, 3-bromopropyl group, 3-iodo Propyl group,
Isopropyl group, 2,2,2,2 ′, 2 ′, 2′-hexafluoroisopropyl group, perfluoroisopropyl group,
Butyl group, 4-fluorobutyl group, 4,4,4-trifluorobutyl group, perfluorobutyl group, 4-chlorobutyl group, 4,4,4-trichlorobutyl group, 4-bromobutyl group, 4-iodobutyl group, s-butyl group, t-butyl group,
Pentyl group, 5-fluoropentyl group, 5,5,5-trifluoropentyl group, perfluoropentyl group, 5-chloropentyl group, 5,5,5-trichloropentyl group, 5-bromopentyl group, 5-iodo Pentyl group,
2-cyanoethyl group, 2,2-dicyanoethyl group, 3-cyanopropyl group, 3,3-dicyanopropyl group, 4-cyanobutyl group, 4,4-dicyanobutyl group, 5-fluoropentyl group, 5,5- Dicyanopentyl group,
2-methoxyethyl group, 3-methoxypropyl group, 4-methoxybutyl group, 5-methoxypentyl group, 2-ethoxyethyl group, 3-ethoxypropyl group, 4-ethoxybutyl group, 5-ethoxypentyl group, 2- Propoxyethyl group, 3-propoxypropyl group, 4-propoxybutyl group, 5-propoxypentyl group, 2-butoxyethyl group, 3-butoxypropyl group, 4-butoxybutyl group, 5-butoxypentyl group,
2-methylthioethyl group, 3-methylthiopropyl group, 4-methylthiobutyl group, 5-methylthiopentyl group, 2-ethylthioethyl group, 3-ethylthiopropyl group, 4-ethylthiobutyl group, 5-ethylthiopentyl Group, 2-propylthioethyl group, 3-propylthiopropyl group, 4-propylthiobutyl group, 5-propylthiopentyl group, 2-butylthioethyl group, 3-butylthiopropyl group, 4-butylthiobutyl group , 5-butylthiopentyl group,
2-methanesulfinylethyl group, 3-methanesulfinylpropyl group, 4-methanesulfinylbutyl group, 5-methanesulfinylpentyl group, 2-ethanesulfinylethyl group, 3-ethanesulfinylpropyl group, 4-ethanesulfinylbutyl group, 5 -Ethanesulfinylpentyl group, 2-propanesulfinylethyl group, 3-propanesulfinylpropyl group, 4-propanesulfinylbutyl group, 5-propanesulfinylpentyl group, 2-butanesulfinylethyl group, 3-butanesulfinylpropyl group, 4- Butanesulfinylbutyl group, 5-butanesulfinylpentyl group,
2-methanesulfonylethyl group, 3-methanesulfonylpropyl group, 4-methanesulfonylbutyl group, 5-methanesulfonylpentyl group, 2-ethanesulfonylethyl group, 3-ethanesulfonylpropyl group, 4-ethanesulfonylbutyl group, 5 -Ethanesulfonylpentyl group, 2-propanesulfonylethyl group, 3-propanesulfonylpropyl group, 4-propanesulfonylbutyl group, 5-propanesulfonylpentyl group, 2-butanesulfonylethyl group, 3-butanesulfonylpropyl group, 4- Examples include butanesulfonylbutyl group and 5-butanesulfonylpentyl group.
Examples of the “C3 to C5 cycloalkyl group” include a cyclopropyl group, a cyclobutyl group, and a cyclopentyl group.
Examples of the “C1-C5 chain hydrocarbon group optionally substituted with one or more groups selected from group C” include cyclopropylmethyl group, 2-cyclopropylethyl group, 3-cyclopropylpropyl group, 4 -Cyclopropylbutyl group, 5-cyclopropylpentyl group,
Methyl group, fluoromethyl group, difluoromethyl group, trifluoromethyl group, chloromethyl group, dichloromethyl group, trichloromethyl group, bromomethyl group, dibromomethyl group, iodomethyl group, chlorodifluoromethyl group,
Ethyl group, 2-fluoroethyl group, 2,2,2-trifluoroethyl group, perfluoroethyl group, 2-chloroethyl group, 2,2,2-trichloroethyl group, 2-bromoethyl group, 2-iodoethyl group,
Propyl group, 3-fluoropropyl group, 3,3,3-trifluoropropyl group, perfluoropropyl group, isopropyl group, 2,2,2,2 ′, 2 ′, 2′-hexafluoroisopropyl group, perfluoro Isopropyl group, 3-chloropropyl group, 3,3,3-trichloropropyl group, 3-bromopropyl group, 3-iodopropyl group,
Butyl group, 4-fluorobutyl group, 4,4,4-trifluorobutyl group, perfluorobutyl group, 4-chlorobutyl group, 4,4,4-trichlorobutyl group, 4-bromobutyl group, 4-iodobutyl group, s-butyl group, t-butyl group,
Pentyl group, 5-fluoropentyl group, 5,5,5-trifluoropentyl group, perfluoropentyl group, 5-chloropentyl group, 5,5,5-trichloropentyl group, 5-bromopentyl group, 5-iodo Pentyl group,
Cyanomethyl group, dicyanomethyl group, 2-cyanoethyl group, 2,2-dicyanoethyl group, 3-cyanopropyl group, 3,3-dicyanopropyl group, 4-cyanobutyl group, 4,4-dicyanobutyl group, 5-cyano Pentyl group, 5,5-dicyanopentyl group,
Methoxymethyl group, ethoxymethyl group, propoxymethyl group, isopropoxymethyl group, butoxymethyl group, isobutoxymethyl group, t-butoxymethyl group, 2-methoxyethyl group, 3-methoxypropyl group, 4-methoxybutyl group, 5-methoxypentyl group, 2-ethoxyethyl group, 3-ethoxypropyl group, 4-ethoxybutyl group, 5-ethoxypentyl group, 2-propoxyethyl group, 3-propoxypropyl group, 4-propoxybutyl group, 5- Propoxypentyl group, 2-butoxyethyl group, 3-butoxypropyl group, 4-butoxybutyl group, 5-butoxypentyl group,
Methylthiomethyl group, ethylthiomethyl group, propylthiomethyl group, isopropylthiomethyl group, butylthiomethyl group, isobutylthiomethyl group, t-butylthiomethyl group, 2-methylthioethyl group, 3-methylthiopropyl group, 4- Methylthiobutyl group, 5-methylthiopentyl group, 2-ethylthioethyl group, 3-ethylthiopropyl group, 4-ethylthiobutyl group, 5-ethylthiopentyl group, 2-propylthioethyl group, 3-propylthiopropyl group Group, 4-propylthiobutyl group, 5-propylthiopentyl group, 2-butylthioethyl group, 3-butylthiopropyl group, 4-butylthiobutyl group, 5-butylthiopentyl group,
Methanesulfinylmethyl group, ethanesulfinylmethyl group, propanesulfinylmethyl group, isopropanesulfinylmethyl group, butanesulfinylmethyl group, isobutanesulfinylmethyl group, t-butanesulfinylmethyl group, 2-methanesulfinylethyl group, 3-methanesulfinylpropyl group Group, 4-methanesulfinylbutyl group, 5-methanesulfinylpentyl group, 2-ethanesulfinylethyl group, 3-ethanesulfinylpropyl group, 4-ethanesulfinylbutyl group, 5-ethanesulfinylpentyl group, 2-propanesulfinylethyl group 3-propanesulfinylpropyl group, 4-propanesulfinylbutyl group, 5-propanesulfinylpentyl group, 2-butanesulfinylethyl group, 3-butanesulfy group Rupuropiru group, 4-Bed ethanesulfinyl butyl group, 5- butane sulfinyl point pen butyl group,
Methanesulfonylmethyl group, ethanesulfonylmethyl group, propanesulfonylmethyl group, isopropanesulfonylmethyl group, butanesulfonylmethyl group, isobutanesulfonylmethyl group, t-butanesulfonylmethyl group, 2-methanesulfonylethyl group, 3-methanesulfonylpropyl group Group, 4-methanesulfonylbutyl group, 5-methanesulfonylpentyl group, 2-ethanesulfonylethyl group, 3-ethanesulfonylpropyl group, 4-ethanesulfonylbutyl group, 5-ethanesulfonylpentyl group, 2-propanesulfonylethyl group 3-propanesulfonylpropyl group, 4-propanesulfonylbutyl group, 5-propanesulfonylpentyl group, 2-butanesulfonylethyl group, 3-butanesulfonylpropyl group, 4-butanesulfonylbutyl group And it includes 5-butane sulfonyl pentyl group.
Examples of the “C3-C10 cycloalkyl group optionally substituted with one or more groups selected from group D” include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclononyl. Group, cyclodecyl group, methylcyclopropyl group, 1,1-dimethylcyclopropyl group, ethylcyclopropyl group, propylcyclopropyl group, butylcyclopropyl group, pentylcyclopropyl group, 2-methylcyclohexyl group, 2-ethylcyclohexyl group 2-propylcyclohexyl group, 2-butylcyclohexyl group, 2-pentylcyclohexyl group, 3-methylcyclohexyl group, 3-ethylcyclohexyl group, 3-propylcyclohexyl group, 3-butylcyclohexyl group, 3-pentylcyclo Hexyl group, 4-methylcyclohexyl group, 4-ethylcyclohexyl group, 4-propylcyclohexyl group, 4-butylcyclohexyl group, 4-pentylcyclohexyl group, fluorocyclopropyl group, chlorocyclopropyl group, 1,1-difluorocyclopropyl Group, 1,1-dichlorocyclopropyl group, 2-fluorocyclohexyl group, 3-fluorocyclohexyl group, 4-fluorocyclohexyl group, 2-chlorocyclohexyl group, 3-chlorocyclohexyl group and 4-chlorocyclohexyl group.
Examples of the “phenyl group optionally substituted with one or more groups selected from group E” include, for example, phenyl group, 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 2-bromophenyl group, 3-bromophenyl group, 4-bromophenyl group, 2-iodophenyl group, 3-iodophenyl group, 4-iodophenyl group, 2-cyanophenyl Group, 3-cyanophenyl group, 4-cyanophenyl group, 2-nitrophenyl group, 3-nitrophenyl group, 4-nitrophenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 2-ethylphenyl group, 3-ethylphenyl group, 4-ethylphenyl group, 2-propylphenyl group, 3-propylpheny Group, 4-propylphenyl group, 2-isopropylphenyl group, 3-isopropylphenyl group, 4-isopropylphenyl group, 2-butylphenyl group, 3-butylphenyl group, 4-butylphenyl group, 2-isobutylphenyl group, 3-isobutylphenyl group, 4-isobutylphenyl group, 2-t-butylphenyl group, 3-t-butylphenyl group, 4-t-butylphenyl group, 2-pentylphenyl group, 3-hexylphenyl group, 4- Heptylphenyl group, 2-octylphenyl group, 3-nonylphenyl group, 4-decylphenyl group, 2-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 4-trifluoromethylphenyl group, 2- (2 , 2,2-trifluoroethyl) phenyl group, 3- (3,3,3-trifluoropropyl) Phenyl group, 4- (4,4,4-trifluorobutyl) phenyl group, 2- (5,5,5-trifluoropentyl) phenyl group, 3- (6,6,6-trifluorohexyl) phenyl group 4- (7,7,7-trifluoroheptyl) phenyl group, 2- (8,8,8-trifluorooctyl) phenyl group, 3- (9,9,9-trifluorononyl) phenyl group, 4 -(10,10,10-trifluorodecyl) phenyl group,
2-cyclopropylphenyl group, 3-cyclopropylphenyl group, 4-cyclopropylphenyl group, 2-cyclobutylphenyl group, 3-cyclopentylphenyl group, 4-cyclohexylphenyl group, 2-cycloheptylphenyl group, 3-cyclo Octylphenyl group, 4-cyclononylphenyl group, 2-cyclodecylphenyl group, 3- (methylcyclopropyl) phenyl group, 4- (1,1-dimethylcyclopropyl) phenyl group, 3- (fluorocyclopropyl) phenyl Group, 4- (chlorocyclopropyl) phenyl group, 2- (1,1-difluorocyclopropyl) phenyl group, 3- (1,1-dichlorocyclopropyl) phenyl group, 4- (2-fluorocyclohexyl) phenyl group 4- (2-chlorocyclohexyl) phenyl group,
2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 2-trifluoromethoxyphenyl group, 3-trifluoromethoxyphenyl group, 4-trifluoromethoxyphenyl group, 2-ethoxyphenyl group, 3- Propoxyphenyl group, 4-butoxyphenyl group,
2-methylthiophenyl group, 3-methylthiophenyl group, 4-methylthiophenyl group, 2-trifluoromethylthiophenyl group, 3-trifluoromethylthiophenyl group, 4-trifluoromethylthiophenyl group, 2-ethylthiophenyl group, 3 -Propylthiophenyl group, 4-butylthiophenyl group,
2-methanesulfinylphenyl group, 3-methanesulfinylphenyl group, 4-methanesulfinylphenyl group, 2-methanesulfinylphenyl group, 3-methanesulfinylphenyl group, 4-methanesulfinylphenyl group, 2-ethylsulfinylphenyl group, 3 -Propylsulfinylphenyl group, 4-butylsulfinylphenyl group,
2-methanesulfonylphenyl group, 3-methanesulfonylphenyl group, 4-methanesulfonylphenyl group, 2-methanesulfonylphenyl group, 3-methanesulfonylphenyl group, 4-methanesulfonylphenyl group, 2-ethylsulfonylphenyl group, 3 -Propylsulfonylphenyl group, 4-butylsulfonylphenyl group, 2-acetylphenyl group, 3-acetylphenyl group, 4-acetylphenyl group, 2-difluoroacetylphenyl group, 3-trifluoroacetylphenyl group, 4-dichloroacetyl Phenyl group, 2-trichloroacetylphenyl group, 3-propanoylphenyl group, 4-butanoylphenyl group, 2-isobutanoylphenyl group, 3-pentanoylphenyl group, 4-pivaloylphenyl group,
2- (methoxycarbonyl) phenyl group, 3- (methoxycarbonyl) phenyl group, 4- (methoxycarbonyl) phenyl group, 2- (trifluoromethoxycarbonyl) phenyl group, 3- (trichloromethoxycarbonyl) phenyl group, 4- (Ethoxycarbonyl) phenyl group, 2- (propoxycarbonyl) phenyl group, 3- (isopropoxycarbonyl) phenyl group, 4- (butoxycarbonyl) phenyl group,
2-acetoxyphenyl group, 3-acetoxyphenyl group, 4-acetoxyphenyl group, 2-difluoroacetoxyphenyl group, 3-trifluoroacetoxyphenyl group, 4-trichloroacetoxyphenyl group, 2-propanoyloxyphenyl group, 3- Examples include butanoyloxyphenyl group, 4-isobutanoyloxyphenyl group, 2-pentanoyloxyphenyl group and 3-pivaloyloxyphenyl group.
Examples of the “C2-C5 polymethylene group optionally substituted with one or more groups selected from group E” include, for example, an ethylene group, a 1,3-propylene group, a 1,4-butylene group, and a 1,5-pentylene group. , Fluoroethylene group, chloroethylene group, bromoethylene group, cyanoethylene group, nitroethylene group, 1,2-propylene group, 3,3,3-trifluoro-1,2-propylene group, cyclopropylethylene group, methoxy Ethylene group, trifluoromethoxyethylene group, methylthioethylene group, trifluoromethylthioethylene group, methanesulfinylethylene group, trifluoromethanesulfinylethylene group, methanesulfonylethylene group, trifluoromethanesulfonylethylene group, acetylethylene group, trifluoroacetylethylene group , Methoxycal Examples thereof include bonylethylene group, trifluoromethoxycarbonylethylene group, acetoxyethylene group and trifluoroacetoxyethylene group.
Examples of the “propene-1,3-diyl group optionally substituted with one or more groups selected from group E” include propene-1,3-diyl group, 2-fluoropropene-1,3-diyl group 3-fluoropropene-1,3-diyl group, 3,3-difluoropropene-1,3-diyl group, 2-chloropropene-1,3-diyl group, 2-bromopropene-1,3-diyl group 2-cyanopropene-1,3-diyl group, 2-nitropropene-1,3-diyl group, 2-methylpropene-1,3-diyl group, 3-methylpropene-1,3-diyl group, 3 , 3-Dimethylpropene-1,3-diyl group, 2-trifluoromethylpropene-1,3-diyl group, 2-cyclopropylpropene-1,3-diyl group, 2-methoxypropene-1,3-diyl Group, 2-trif Olomethoxypropene-1,3-diyl group, 2-methylthiopropene-1,3-diyl group, 2-trifluoromethylthiopropene-1,3-diyl group, 2-methanesulfinylpropene-1,3-diyl group, 2-trifluoromethanesulfinylpropene-1,3-diyl group, 2-acetylpropene-1,3-diyl group, 2-trifluoroacetylpropene-1,3-diyl group, 2-methoxycarbonylpropene-1,3- Examples include a diyl group, a 2-trifluoromethoxycarbonylpropene-1,3-diyl group, a 2-acetoxypropene-1,3-diyl group, and a 2-trifluoroacetoxypropene-1,3-diyl group.
Examples of the “1,3-butadiene-1,4-diyl group optionally substituted with one or more groups selected from group E” include 1,3-butadiene-1,4-diyl group, 1-fluoro -1,3-butadiene-1,4-diyl group, 2-fluoro-1,3-butadiene-1,4-diyl group, 1-chloro-1,3-butadiene-1,4-diyl group, 2- Chloro-1,3-butadiene-1,4-diyl group, 1-bromo-1,3-butadiene-1,4-diyl group, 2-bromo-1,3-butadiene-1,4-diyl group, 1 -Cyano-1,3-butadiene-1,4-diyl group, 1-nitro-1,3-butadiene-1,4-diyl group, 1-methyl-1,3-butadiene-1,4-diyl group, 2-methyl-1,3-butadiene-1,4-diyl group, 1-trifluoromethyl -1,3-butadiene-1,4-diyl group, 1-cyclopropyl-1,3-butadiene-1,4-diyl group, 1-methoxy-1,3-butadiene-1,4-diyl group, 1 -Trifluoromethoxy-1,3-butadiene-1,4-diyl group, 1-methylthio-1,3-butadiene-1,4-diyl group, 1-trifluoromethylthio-1,3-butadiene-1, 4-diyl group, 1-methanesulfinyl-1,3-butadiene-1,4-diyl group, 1-trifluoromethanesulfinyl-1,3-butadiene-1,4-diyl group, 1-acetyl-1,3- Butadiene-1,4-diyl group, 1-trifluoroacetyl-1,3-butadiene-1,4-diyl group, 1-methoxycarbonyl-1,3-butadiene-1,4-diyl group, 1-trifluoro Methoxycarbonyl-1,3-butadiene-1,4-diyl group, 1-acetoxy-1,3-butadiene-1,4-diyl group and 1-trifluoroacetoxy-1,3-butadiene-1,4-diyl Groups.
Examples of the “C1-C4 chain hydrocarbon group” include methyl group, ethyl group, ethynyl group, propyl group, isopropyl group, allyl group, propargyl group, butyl group, isobutyl group and t-butyl group.
Examples of the “C1-C10 chain hydrocarbon group optionally substituted with one or more groups selected from group C” include cyclopropylmethyl group, 2-cyclopropylethyl group, 3-cyclopropylpropyl group, 4 -Cyclopropylbutyl group, 5-cyclopropylpentyl group,
Methyl group, fluoromethyl group, difluoromethyl group, trifluoromethyl group, chloromethyl group, dichloromethyl group, trichloromethyl group, bromomethyl group, dibromomethyl group, iodomethyl group,
Ethyl group, 2-fluoroethyl group, 2,2,2-trifluoroethyl group, perfluoroethyl group, 2-chloroethyl group, 2,2,2-trichloroethyl group, 2-bromoethyl group, 2-iodoethyl group,
Propyl group, 3-fluoropropyl group, 3,3,3-trifluoropropyl group, perfluoropropyl group, isopropyl group, 2,2,2,2 ′, 2 ′, 2′-hexafluoroisopropyl group, perfluoro Isopropyl group, 3-chloropropyl group, 3,3,3-trichloropropyl group, 3-bromopropyl group, 3-iodopropyl group,
Butyl group, 4-fluorobutyl group, 4,4,4-trifluorobutyl group, perfluorobutyl group, 4-chlorobutyl group, 4,4,4-trichlorobutyl group, 4-bromobutyl group, 4-iodobutyl group, s-butyl group, t-butyl group,
Pentyl group, 5-fluoropentyl group, 5,5,5-trifluoropentyl group, perfluoropentyl group, 5-chloropentyl group, 5,5,5-trichloropentyl group, 5-bromopentyl group, 5-iodo Pentyl group,
Hexyl group, 6,6,6-trifluorohexyl group, 6-chlorohexyl group,
Heptyl group, 7,7,7-trifluoroheptyl group, 7-chloroheptyl group,
Octyl group, 8,8,8, -trifluorooctyl group, 8-chlorooctyl group, nonyl group, 9,9,9-trifluorononyl group, 9-chlorononyl group,
Decyl group, 10,10,10-trifluorodecyl group, 10-chlorodecyl group, cyanomethyl group, dicyanomethyl group, 2-cyanoethyl group, 2,2-dicyanoethyl group, 3-cyanopropyl group, 3,3-dicyano Propyl group, 4-cyanobutyl group, 4,4-dicyanobutyl group, 5-cyanopentyl group, 5,5-dicyanopentyl group,
Methoxymethyl group, ethoxymethyl group, propoxymethyl group, isopropoxymethyl group, butoxymethyl group, isobutoxymethyl group, t-butoxymethyl group, 2-methoxyethyl group, 3-methoxypropyl group, 4-methoxybutyl group, 5-methoxypentyl group, 2-ethoxyethyl group, 3-ethoxypropyl group, 4-ethoxybutyl group, 5-ethoxypentyl group, 2-propoxyethyl group, 3-propoxypropyl group, 4-propoxybutyl group, 5- Propoxypentyl group, 2-butoxyethyl group, 3-butoxypropyl group, 4-butoxybutyl group, 5-butoxypentyl group,
Methylthiomethyl group, ethylthiomethyl group, propylthiomethyl group, isopropylthiomethyl group, butylthiomethyl group, isobutylthiomethyl group, t-butylthiomethyl group, 2-methylthioethyl group, 3-methylthiopropyl group, 4- Methylthiobutyl group, 5-methylthiopentyl group, 2-ethylthioethyl group, 3-ethylthiopropyl group, 4-ethylthiobutyl group, 5-ethylthiopentyl group, 2-propylthioethyl group, 3-propylthiopropyl group Group, 4-propylthiobutyl group, 5-propylthiopentyl group, 2-butylthioethyl group, 3-butylthiopropyl group, 4-butylthiobutyl group, 5-butylthiopentyl group,
Methanesulfinylmethyl group, ethanesulfinylmethyl group, propanesulfinylmethyl group, isopropanesulfinylmethyl group, butanesulfinylmethyl group, isobutanesulfinylmethyl group, t-butanesulfinylmethyl group, 2-methanesulfinylethyl group, 3-methanesulfinylpropyl group Group, 4-methanesulfinylbutyl group, 5-methanesulfinylpentyl group, 2-ethanesulfinylethyl group, 3-ethanesulfinylpropyl group, 4-ethanesulfinylbutyl group, 5-ethanesulfinylpentyl group, 2-propanesulfinylethyl group 3-propanesulfinylpropyl group, 4-propanesulfinylbutyl group, 5-propanesulfinylpentyl group, 2-butanesulfinylethyl group, 3-butanesulfy group Rupuropiru group, 4-Bed ethanesulfinyl butyl group, 5- butane sulfinyl point pen butyl group,
Methanesulfonylmethyl group, ethanesulfonylmethyl group, propanesulfonylmethyl group, isopropanesulfonylmethyl group, butanesulfonylmethyl group, isobutanesulfonylmethyl group, t-butanesulfonylmethyl group, 2-methanesulfonylethyl group, 3-methanesulfonylpropyl group Group, 4-methanesulfonylbutyl group, 5-methanesulfonylpentyl group, 2-ethanesulfonylethyl group, 3-ethanesulfonylpropyl group, 4-ethanesulfonylbutyl group, 5-ethanesulfonylpentyl group, 2-propanesulfonylethyl group 3-propanesulfonylpropyl group, 4-propanesulfonylbutyl group, 5-propanesulfonylpentyl group, 2-butanesulfonylethyl group, 3-butanesulfonylpropyl group, 4-butanesulfonylbutyl group And it includes 5-butane sulfonyl pentyl group.
Examples of the “C1-C4 alkoxy group” include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, and a t-butoxy group.
Examples of the “C1-C4 alkylthio group” include a methylthio group, an ethylthio group, a propylthio group, an isopropylthio group, a butylthio group, an isobutylthio group, and a t-butylthio group.
Examples of the “C1-C4 alkylsulfinyl group” include a methanesulfinyl group, an ethanesulfinyl group, a propanesulfinyl group, an isopropanesulfinyl group, a butanesulfinyl group, an isobutanesulfinyl group, and a t-butanesulfinyl group.
Examples of the “C1-C4 alkylsulfonyl group” include a methanesulfonyl group, an ethanesulfonyl group, a propanesulfonyl group, an isopropanesulfonyl group, a butanesulfonyl group, an isobutanesulfonyl group, and a t-butanesulfonyl group.
Examples of the “C1-C4 alkoxy group optionally substituted with halogen” include a methoxy group, a fluoromethoxy group, a difluoromethoxy group, a trifluoromethoxy group, a chloromethoxy group, a dichloromethoxy group, a trichloromethoxy group, and a bromomethoxy group. , Dibromomethoxy group, iodomethoxy group, chlorodifluoromethoxy group,
Ethoxy group, 2-fluoroethoxy group, 2,2,2-trifluoroethoxy group, perfluoroethoxy group, 2-chloroethoxy group, 2,2,2-trichloroethoxy group, 2-bromoethoxy group, 2-iodo An ethoxy group,
Propoxy group, 3-fluoropropoxy group, 3,3,3-trifluoropropoxy group, perfluoropropoxy group, 2,2,2,2 ′, 2 ′, 2′-hexafluoroisopropoxy group, perfluoroisopropoxy group Group, 3-chloropropoxy group, 3,3,3-trichloropropoxy group, 3-bromopropoxy group, 3-iodopropoxy group,
Butoxy group, 4-fluorobutoxy group, 4,4,4-trifluorobutoxy group, perfluorobutoxy group, 4-chlorobutoxy group, 4,4,4-trichlorobutoxy group, 4-bromobutoxy group and 4-iodo A butoxy group is mentioned.
Examples of the “C1-C4 alkylthio group optionally substituted with halogen” include a methylthio group, a fluoromethylthio group, a difluoromethylthio group, a trifluoromethylthio group, a chloromethylthio group, a dichloromethylthio group, a trichloromethylthio group, and a bromomethylthio group. , Dibromomethylthio group, iodomethylthio group, chlorodifluoromethylthio group,
Ethylthio group, 2-fluoroethylthio group, 2,2,2-trifluoroethylthio group, perfluoroethylthio group, 2-chloroethylthio group, 2,2,2-trichloroethylthio group, 2-bromoethyl A thio group, a 2-iodoethylthio group,
Propylthio group, 3-fluoropropylthio group, 3,3,3-trifluoropropylthio group, perfluoropropylthio group, 2,2,2,2 ′, 2 ′, 2′-hexafluoroisopropylthio group, Fluoroisopropylthio group, 3-chloropropylthio group, 3,3,3-trichloropropylthio group, 3-bromopropylthio group, 3-iodopropylthio group,
Butylthio group, 4-fluorobutylthio group, 4,4,4-trifluorobutylthio group, perfluorobutylthio group, 4-chlorobutylthio group, 4,4,4-trichlorobutylthio group, 4-bromobutyl A thio group and a 4-iodobutylthio group are mentioned.
Examples of the “C1-C4 alkylsulfinyl group optionally substituted with halogen” include methanesulfinyl group, fluoromethanesulfinyl group, difluoromethanesulfinyl group, trifluoromethanesulfinyl group, chloromethanesulfinyl group, dichloromethanesulfinyl group, trichloromethane. Sulfinyl group, bromomethanesulfinyl group, dibromomethanesulfinyl group, iodomethanesulfinyl group, chlorodifluoromethanesulfinyl group,
Ethanesulfinyl group, 2-fluoroethanesulfinyl group, 2,2,2-trifluoroethanesulfinyl group, perfluoroethanesulfinyl group, 2-chloroethanesulfinyl group, 2,2,2-trichloroethanesulfinyl group, 2-bromoethanesulfinyl group Group, 2-iodoethanesulfinyl group,
Propanesulfinyl group, 3-fluoropropanesulfinyl group, 3,3,3-trifluoropropanesulfinyl group, perfluoropropanesulfinyl group, isopropanesulfinyl group, 2,2,2,2 ′, 2 ′, 2′-hexa Fluoroisopropanesulfinyl group, perfluoroisopropanesulfinyl group, 3-chloropropanesulfinyl group, 3,3,3-trichloropropanesulfinyl group, 3-bromopropanesulfinyl group, 3-iodopropanesulfinyl group, butanesulfinyl group, 4- Fluorobutanesulfinyl group, 4,4,4-trifluorobutanesulfinyl group, perfluorobutanesulfinyl group, 4-chlorobutanesulfinyl group, 4,4,4-trichlorobutanesulfinyl group, 4-bromobutanesulfinyl group It includes groups and 4-iodo Bed ethanesulfinyl group.
Examples of the “optionally substituted C1-C4 alkylsulfonyl group” include a methanesulfonyl group, a fluoromethanesulfonyl group, a difluoromethanesulfonyl group, a trifluoromethanesulfonyl group, a chloromethanesulfonyl group, a dichloromethanesulfonyl group, and trichloromethane. Sulfonyl group, bromomethanesulfonyl group, dibromomethanesulfonyl group, iodomethanesulfonyl group, chlorodifluoromethanesulfonyl group,
Ethanesulfonyl group, 2-fluoroethanesulfonyl group, 2,2,2-trifluoroethanesulfonyl group, perfluoroethanesulfonyl group, 2-chloroethanesulfonyl group, 2,2,2-trichloroethanesulfonyl group, 2-bromoethanesulfonyl Group, 2-iodoethanesulfonyl group,
Propanesulfonyl group, 3-fluoropropanesulfonyl group, 3,3,3-trifluoropropanesulfonyl group, perfluoropropanesulfonyl group, isopropanesulfonyl group, 2,2,2,2 ′, 2 ′, 2′-hexa Fluoroisopropanesulfonyl group, perfluoroisopropanesulfonyl group, 3-chloropropanesulfonyl group, 3,3,3-trichloropropanesulfonyl group, 3-bromopropanesulfonyl group, 3-iodopropanesulfonyl group,
Butanesulfonyl group, 4-fluorobutanesulfonyl group, 4,4,4-trifluorobutanesulfonyl group, perfluorobutanesulfonyl group, 4-chlorobutanesulfonyl group, 4,4,4-trichlorobutanesulfonyl group, 4-bromo A butanesulfonyl group and a 4-iodobutanesulfonyl group are mentioned.
Examples of the “(C1-C4 alkyl) carbonyl group optionally substituted with halogen” include acetyl group, fluoroacetyl group, difluoroacetyl group, trifluoroacetyl group, chloroacetyl group, dichloroacetyl group, trichloroacetyl group, Bromoacetyl group, dibromoacetyl group, iodoacetyl group, chlorodifluoroacetyl group,
Propanoyl group, 3-fluoropropanoyl group, 3,3,3-trifluoropropanoyl group, perfluoropropanoyl group, 3-chloropropanoyl group, 3,3,3-trichloropropanoyl group, 3-bromopropanoyl group Noyl group, 3-iodopropanoyl group,
Butanoyl group, 4-fluorobutanoyl group, 4,4,4-trifluorobutanoyl group, perfluorobutanoyl group, 3,3,3,3 ′, 3 ′, 3′-hexafluoroisobutanoyl group, Perfluoroisobutanoyl group, 4-chlorobutanoyl group, 4,4,4-trichlorobutanoyl group, 4-bromobutanoyl group, 4-iodobutanoyl group, isobutanoyl group, 2,2,2,2 ′ , 2 ′, 2′-hexafluoroisobutanoyl group, perfluoroisobutanoyl group,
Pentanoyl group, 5-fluoropentanoyl group, 5,5,5-trifluoropentanoyl group, perfluoropentanoyl group, 5-chloropentanoyl group, 5,5,5-trichloropentanoyl group, 5-bromopenta Examples include a noyl group, a 5-iodopentanoyl group, and a pivaloyl group.
Examples of the “optionally substituted (C1-C4 alkoxy) carbonyl group with halogen” include a methoxycarbonyl group, a fluoromethoxycarbonyl group, a difluoromethoxycarbonyl group, a trifluoromethoxycarbonyl group, a chloromethoxycarbonyl group, and a dichloromethoxycarbonyl group. Group, trichloromethoxycarbonyl group, bromomethoxycarbonyl group, dibromomethoxycarbonyl group, iodomethoxycarbonyl group, chlorodifluoromethoxycarbonyl group,
Ethoxycarbonyl group, 2-fluoroethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl group, perfluoroethoxycarbonyl group, 2-chloroethoxycarbonyl group, 2,2,2-trichloroethoxycarbonyl group, 2-bromo Ethoxycarbonyl group, 2-iodoethoxycarbonyl group,
Propoxycarbonyl group, 3-fluoropropoxycarbonyl group, 3,3,3-trifluoropropoxycarbonyl group, perfluoropropoxycarbonyl group, isopropoxycarbonyl group, 2,2,2,2 ′, 2 ′, 2′-hexa Fluoroisopropoxycarbonyl group, perfluoroisopropoxycarbonyl group, 3-chloropropoxycarbonyl group, 3,3,3-trichloropropoxycarbonyl group, 3-bromopropoxycarbonyl group, 3-iodopropoxycarbonyl group,
Butoxycarbonyl group, 4-fluorobutoxycarbonyl group, 4,4,4-trifluorobutoxycarbonyl group, perfluorobutoxycarbonyl group, 4-chlorobutoxycarbonyl group, 4,4,4-trichlorobutoxycarbonyl group, 4-bromo A butoxycarbonyl group, a 4-iodobutoxycarbonyl group, and a t-butoxycarbonyl group are mentioned.
Examples of the “(C1-C4 alkyl) carbonyloxy group optionally substituted with halogen” include, for example, an acetoxy group, a fluoroacetoxy group, a difluoroacetoxy group, a trifluoroacetoxy group, a chloroacetoxy group, a dichloroacetoxy group, and a trichloroacetoxy group , Bromoacetoxy group, dibromoacetoxy group, iodoacetoxy group, chlorodifluoroacetoxy group,
Propanoyloxy group, 3-fluoropropanoyloxy group, 3,3,3-trifluoropropanoyloxy group, perfluoropropanoyloxy group, 3-chloropropanoyloxy group, 3,3,3-trichloropropanoyl An oxy group, a 3-bromopropanoyloxy group, a 3-iodopropanoyloxy group,
Butanoyloxy group, 4-fluorobutanoyloxy group, 4,4,4-trifluorobutanoyloxy group, perfluorobutanoyloxy group, isobutanoyloxy group, 3,3,3,3 ′, 3 ′ , 3′-hexafluoroisobutanoyloxy group, perfluoroisobutanoyloxy group, 4-chlorobutanoyloxy group, 4,4,4-trichlorobutanoyloxy group, 4-bromobutanoyloxy group, 4- Iodobutanoyloxy group, pentanoyloxy group, 5-fluoropentanoyloxy group, 5,5,5-trifluoropentanoyloxy group, perfluoropentanoyloxy group, 5-chloropentanoyloxy group, 5,5 , 5-trichloropentanoyloxy group, 5-bromopentanoyloxy group, 5-iodopentanoyloxy group and piva Yloxy group, and the like.
Examples of the “C1-C5 alkyl group” include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a t-butyl group, and a pentyl group.
Examples of the “C1-C10 chain hydrocarbon group optionally substituted with halogen” include a methyl group, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a chloromethyl group, a dichloromethyl group, a trichloromethyl group, Bromomethyl group, dibromomethyl group, iodomethyl group, chlorodifluoromethyl group,
Ethyl group, 2-fluoroethyl group, 2,2,2-trifluoroethyl group, perfluoroethyl group, 2-chloroethyl group, 2,2,2-trichloroethyl group, 2-bromoethyl group, 2-iodoethyl group,
Propyl group, 3-fluoropropyl group, 3,3,3-trifluoropropyl group, perfluoropropyl group, isopropyl group, 2,2,2,2 ′, 2 ′, 2′-hexafluoroisopropyl group, perfluoro Isopropyl group, 3-chloropropyl group, 3,3,3-trichloropropyl group, 3-bromopropyl group, 3-iodopropyl group,
Butyl group, 4-fluorobutyl group, 4,4,4-trifluorobutyl group, perfluorobutyl group, 4-chlorobutyl group, 4,4,4-trichlorobutyl group, 4-bromobutyl group, 4-iodobutyl group, s-butyl group, t-butyl group,
Pentyl group, 5-fluoropentyl group, 5,5,5-trifluoropentyl group, perfluoropentyl group, 5-chloropentyl group, 5,5,5-trichloropentyl group, 5-bromopentyl group and 5-iodo A pentyl group is mentioned.
As an aspect of this invention compound, the following amide compounds are mentioned, for example.
In formula (1), R ¹ An amide compound in which is a C1-C5 chain hydrocarbon group optionally substituted with one or more groups selected from hydrogen, halogen or group B;
In formula (1), R ¹ An amide compound in which is hydrogen, halogen, or a C1-C5 chain hydrocarbon group optionally substituted with halogen;
In formula (1), R ¹ An amide compound wherein is hydrogen, halogen, or a methyl group which may be substituted with halogen;
In formula (1), R ¹ An amide compound in which is hydrogen, halogen or methyl;
In formula (1), R ¹ An amide compound in which is hydrogen;
In formula (1), R ² An amide compound in which is a halogen;
In formula (1), R ² An amide compound wherein is chlorine;
In formula (1), p is 1 and R ² An amide compound in which is a halogen;
In formula (1), p is 1 and R ² An amide compound wherein is chlorine;
In formula (1), p is 1 and R ² An amide compound in which is chlorine at the 2-position on the benzene ring;
In formula (1), R ³ An amide compound in which is a C1-C5 chain hydrocarbon group optionally substituted with one or more groups selected from group C;
In formula (1), R ³ An amide compound in which is a C1-C5 chain hydrocarbon group;
In formula (1), R ³ An amide compound in which is a methyl group;
In formula (1), R ¹ Is hydrogen and R ² An amide compound in which is a halogen;
In formula (1), R ¹ Is hydrogen and R ² An amide compound wherein is chlorine;
In formula (1), R ¹ Is hydrogen, p is 1, and R ² An amide compound wherein is chlorine;
In formula (1), R ¹ Is hydrogen, p is 1, and R ² An amide compound in which is chlorine at the 2-position on the benzene ring;
In formula (1), R ³ Is a methyl group and R ² An amide compound in which is a halogen;
In formula (1), R ³ Is a methyl group and R ² An amide compound wherein is chlorine;
In formula (1), R ³ Is a methyl group, p is 1, and R ² An amide compound wherein is chlorine;
In formula (1), R ³ Is a methyl group, p is 1, and R ² An amide compound in which is chlorine at the 2-position on the benzene ring;
In formula (1), R ¹ Is hydrogen and R ³ An amide compound in which is a C1-C5 chain hydrocarbon group optionally substituted with one or more groups selected from group C;
In formula (1), R ¹ Is hydrogen and R ³ An amide compound in which is a C1-C5 chain hydrocarbon group;
as well as
In formula (1), R ¹ Is hydrogen and R ³ An amide compound in which is a methyl group.
(Production method 1)
The compound of the present invention or a salt thereof can be produced by reacting the compound (3) or a salt thereof with the compound (2) in the presence of a dehydration condensing agent.

[In the formula, R ¹ , R ² , R ³ And p represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as tetrahydrofuran (hereinafter sometimes referred to as THF), ethylene glycol dimethyl ether, tert-butyl methyl ether (hereinafter sometimes referred to as MTBE), hexane, Aliphatic hydrocarbons such as heptane and octane, aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as chlorobenzene, esters such as butyl acetate and ethyl acetate, nitriles such as acetonitrile, N, N -Acid amides such as dimethylformamide (hereinafter sometimes referred to as DMF), sulfoxides such as dimethylsulfoxide (hereinafter sometimes referred to as DMSO), and mixtures thereof.
Examples of the dehydrating condensing agent used in the reaction include 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (hereinafter referred to as WSC), benzotriazol-1-yloxy) tris (dimethylamino) phosphonium hexa Examples thereof include fluorophosphate (hereinafter referred to as BOP reagent) and 1,3-dicyclohexylcarbodiimide.
In the reaction, with respect to 1 mol of the compound (2), the compound (3) is usually used in a proportion of 1 to 3 mol, and the dehydrating condensing agent is usually used in a proportion of 1 to 5 mol.
The reaction temperature of the reaction is usually in the range of 0 to 200 ° C. The reaction time is usually in the range of 1 to 24 hours.
In the reaction, when a BOP reagent is used, the reaction is performed in the presence of a base as necessary. Examples of such bases include tertiary amines such as triethylamine and diisopropylethylamine, and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine.
In the reaction, the base is usually used at a ratio of 1 to 10 mol per 1 mol of the compound (2).
After completion of the reaction, the compound of the present invention can be isolated by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. The isolated compound of the present invention can be further purified by chromatography, recrystallization and the like.
(Production method 2)
The compound of the present invention can be produced by reacting compound (3) or a salt thereof with compound (4) or a salt thereof in the presence of a base.

[In the formula, R ¹ , R ² , R ³ And p represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, and MTBE, aliphatic hydrocarbons such as hexane, heptane, and octane, aromatic hydrocarbons such as toluene and xylene, and halogens such as chlorobenzene. Hydrocarbons, esters such as butyl acetate and ethyl acetate, nitriles such as acetonitrile, acid amides such as DMF, sulfoxides such as DMSO, and mixtures thereof.
Examples of the base used in the reaction include alkali metal carbonates such as sodium carbonate and potassium carbonate, tertiary amines such as triethylamine and diisopropylethylamine, and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine. Can be mentioned.
In the reaction, with respect to 1 mol of the compound (4), the compound (3) is usually used in a proportion of 1 to 3 mol, and the base is usually used in a proportion of 1 to 10 mol.
The reaction temperature is usually in the range of −20 to 140 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound of the present invention can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound of the present invention can be further purified by chromatography, recrystallization and the like.
(Production method 3)
The compound of the present invention can be produced, for example, from compound (5) according to the following scheme.

[In the formula, R ¹ , R ² , R ³ And p represent the same meaning as described above. ]
Step (I-1)
Compound (6) can be produced by reacting compound (5) with compound (3) or a salt thereof in the presence of a dehydration condensing agent.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, and MTBE, aliphatic hydrocarbons such as hexane, heptane, and octane, aromatic hydrocarbons such as toluene and xylene, and halogens such as chlorobenzene. Hydrocarbons, esters such as butyl acetate and ethyl acetate, nitriles such as acetonitrile, acid amides such as DMF, sulfoxides such as DMSO, and mixtures thereof.
Examples of the dehydrating condensing agent used in the reaction include WSC, BOP reagent, and 1,3-dicyclohexylcarbodiimide.
In the reaction, with respect to 1 mol of the compound (5), the compound (3) is usually used in a proportion of 1 to 3 mol, and the dehydrating condensing agent is usually used in a proportion of 1 to 5 mol.
The reaction temperature of the reaction is usually in the range of 0 to 200 ° C. The reaction time is usually in the range of 1 to 24 hours.
In the reaction, when a BOP reagent is used, the reaction is performed in the presence of a base as necessary. Examples of such bases include tertiary amines such as triethylamine and diisopropylethylamine, and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine.
In the reaction, the base is usually used at a ratio of 1 to 10 mol per 1 mol of the compound (5).
After completion of the reaction, the compound (6) can be isolated by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer. The isolated compound (6) can be further purified by chromatography, recrystallization and the like.
Step (I-2)
The compound of the present invention can be produced by reacting the compound (6) with an acid.
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, sulfoxides such as DMSO, methanol, ethanol, 2-methylethanol and the like. Alcohols, acetone, methyl ethyl ketone, ketones such as methyl isobutyl ketone, water and mixtures thereof.
Examples of the acid used in the reaction include inorganic acids such as hydrochloric acid and sulfuric acid, and organic acids such as trifluoroacetic acid, p-toluenesulfonic acid, and methanesulfonic acid.
In the reaction, the acid is usually used in an amount of 1 mol to excess with respect to 1 mol of the compound (6).
The reaction temperature of the reaction is usually in the range of 0 to 150 ° C. The reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, the compound of the present invention can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, and drying and concentration of the organic layer. The isolated compound of the present invention can be further purified by chromatography, recrystallization and the like.
The compound of the present invention is capable of forming an agriculturally acceptable salt. Such a salt of the compound of the present invention is usually a salt of the compound of the present invention and an acid. Examples of the salt with an acid include inorganic acid salts such as hydrochloride, hydrobromide, and sulfate, and organic acid salts such as methanesulfonate, formate, acetate, and trifluoroacetate.
The salt of this invention compound and an acid can be manufactured by making this invention compound react with an acid.

[In the formula, R ¹ , R ² , R ³ And p represent the same meaning as described above, and HX represents an acid. ]
The reaction is performed in the presence of a solvent or in the absence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, and MTBE, aliphatic hydrocarbons such as hexane, heptane, and octane, aromatic hydrocarbons such as toluene and xylene, water, and these. A mixture is mentioned.
Examples of the acid used in the reaction include inorganic acids such as hydrochloric acid, hydrobromic acid, hydroiodic acid, and sulfuric acid, and organic acids such as acetic acid, trifluoroacetic acid, formic acid, p-toluenesulfonic acid, and methanesulfonic acid. Can be mentioned.
In the reaction, an acid is usually used at a ratio of 1 to 100 mol per 1 mol of the compound of the present invention.
The reaction temperature of the reaction is usually in the range of 0 to 200 ° C. The reaction time is usually in the range of 1 to 24 hours.
After completion of the reaction, the salt of the compound of the present invention and the acid can be isolated by removing the unreacted acid.
The plant disease control agent of the present invention contains the compound of the present invention or a salt thereof and an inert carrier (solid carrier, liquid carrier or gas carrier). The plant disease control agent of the present invention is further mixed with a surfactant and other formulation adjuvants, wettable powder, granular wettable powder, flowable powder, granules, dry flowable powder, emulsion, aqueous liquid, oil, Formulated into smoking agents, aerosols, microcapsules and the like. These preparations usually contain the compound of the present invention or a salt thereof in a weight ratio of 0.1 to 99%, preferably 0.2 to 90%.
Examples of the solid support include clays (for example, kaolin, diatomaceous earth, synthetic hydrous silicon oxide, wax clay, bentonite, acid clay, talc), and other inorganic minerals (for example, sericite, quartz powder, sulfur powder, activated carbon). , Calcium carbonate, hydrated silica) and the like. Examples of the liquid carrier include water, alcohols (eg, methanol, ethanol), ketones (eg, acetone, methyl ethyl ketone), aromatic hydrocarbons (eg, benzene, toluene, xylene, ethylbenzene, methylnaphthalene), fat Group hydrocarbons (eg, hexane, cyclohexanone, kerosene), esters (eg, ethyl acetate, butyl acetate), nitriles (eg, acetonitrile, isobutyronitrile), ethers (eg, dioxane, diisopropyl ether), Acid amides (for example, dimethylformamide, dimethylacetamide), halogenated hydrocarbons (for example, dichloroethane, trichloroethylene, carbon tetrachloride) and the like can be mentioned. Examples of the gaseous carrier include dimethyl ether and carbon dioxide.
Examples of the surfactant include alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and polyoxyethylene compounds thereof, polyoxyethylene glycol ethers, polyhydric alcohol esters, sugar alcohol derivatives. Etc.
Other formulation adjuvants include, for example, fixing agents, dispersants, thickeners, wetting agents, extenders and antioxidants, specifically casein, gelatin, polysaccharides (eg starch, arabic gum, cellulose derivatives, Alginic acid), lignin derivatives, bentonite, saccharides, synthetic water-soluble polymers (eg, polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acids), PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4) -Methylphenol), BHA (mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oil, mineral oil, fatty acid or ester thereof, and the like.
The compound of the present invention or a salt thereof is used for controlling plant diseases by applying to a plant or soil where the plant grows. Examples of the method of applying the compound of the present invention or a salt thereof to the plant or the soil where the plant grows include, for example, a method of spraying foliage on the plant, a method of applying to the soil where the plant is grown, and a method of applying to the plant seed. It is done.
In the plant disease control method of the present invention, the plant disease control agent of the present invention is usually used.
In the case where the plant disease control agent of the present invention is used in a method of spraying foliage on a plant or a method of applying to a soil where a plant is cultivated, the application amount of the plant disease control agent of the present invention is 1,000 m. ² The amount of the compound of the present invention or a salt thereof is usually 1 to 500 g, preferably 2 to 200 g. When the plant disease control agent of the present invention is formulated into an emulsion, wettable powder, suspension, etc., the concentration of the compound of the present invention or a salt thereof is usually 0.0005 to 2% by weight, preferably It is diluted with water so as to be 0.005 to 1% by weight. When the plant disease control agent of the present invention is formulated into a powder, granule or the like, the formulation is applied as it is without dilution.
When used in the method of applying the plant disease control agent of the present invention to plant seeds, the application amount of the plant disease control agent of the present invention is usually 0.001 to 1 kg of the present compound or a salt thereof per 1 kg seed. The ratio is 100 g, preferably 0.01 to 50 g.
The plant disease control agent of the present invention can be mixed and / or used in combination with other fungicides, insecticides, acaricides, nematicides, herbicides, plant growth regulators, fertilizers or soil conditioners.
Examples of the active ingredient of such a bactericide include the following.
(1) Azole bactericidal active compound
Propiconazole, Prothioconazole, Triadimenol, Prochloraz, Penconazole, Dibuconazole, Tebuconazole, Tebuconazole, Tebuconazole, Tebuconazole, Tebuconazole, Tebuconazole, Tebuconazole, Tebuconazole, Tebuconazole bromconazole, epoxiconazole, difenoconazole, cyproconazole, metconazole, triflumizole, triflumizole aconazole, microbutanil, fenbuconazole, hexaconazole, fluquinconazole, triticonazole, tertanol, tertanol Hall, flutriafol, simeconazole, ipconazole and the like;
(2) Amine fungicidal active compounds
Fenpropimorph, tridemorph, fenpropidin, spiroxamine and the like;
(3) Benzimidazole bactericidal active compound
Carbendazim, benomyl, thiabendazole, thiophanate-methyl and the like;
(4) Dicarboximide bactericidal active compound
Procymidone, iprodione, vinclozolin and the like;
(5) Anilinopyrimidine bactericidal active compound
Cyprodinil, pyrimethanil, mepanipyrim and the like;
(6) Phenylpyrrole bactericidal active compound
Fenpiclonil, fludioxonil, etc .;
(7) Strobilurin bactericidal active compound
Cresoxime-methyl, azoxystrobin, trifloxystrobin, floxastrobin, picoxystrobin, pyracrostrobin, spirobistrobin (Dimoxystrobin), pyribencarb, methinostrobin, oryzatrobin, enestrobin, etc .;
(8) Phenylamide bactericidal active compound
Metalaxyl, metalaxyl-M or mefenoxam, metalaxyl-M or mexillax, benalaxyl-M, benalaxyl-M or kiralaxyl, etc .;
(9) Carboxylic acid amide fungicidal compound
Dimethomorph, iprovarialcarb, benchavaricarb-isopropyl, mandipropamide, varifenal
(10) Carboxylic acid amide bactericidal active compound
Carboxin, mepronil, flutolanil, thifluzamide, furamethpyr, boscalid, penthiopyrad, fluopyrad, fluopyrad
(11) Other bactericidal active compounds
Dietofencarb; thiuram; fluazinam; mancozeb; chlorothalonil; captan; diclofluanide; folpetto; quinoxifen; Pencyclon; tolcrofosmethyl; carpropamide; diclocimet; phenoxanil; tricyclazole; pyroxilone; probenazole; isotianil; thiazinyl; tebufloquine; ; Oxytetracycline; streptomycin; basic copper chloride; cupric hydroxide; basic copper sulfate; organic copper; sulfur;
Formula (8)

[Where X ¹ Represents hydrogen or halogen, X ² Represents a methyl group, a difluoromethyl group, or a trifluoromethyl group, and Q is any of the following groups:
Q:

Represents. ]
A pyrazolecarboxylic acid amide compound represented by:
Formula (9)

[Where X ³ Represents a methyl group, a difluoromethyl group, or an ethyl group, and X ⁴ Represents a methoxy group or a methylamino group, and X ⁵ Represents a phenyl group, a 2-methylphenyl group, or a 2,5-dimethylphenyl group. ]
An α-alkoxyphenylacetic acid compound represented by:
Formula (10)

[Where X ⁶ Represents a methoxy group, an ethoxy group, a propoxy group, a 2-propenyloxy group, a 2-propynyloxy group, a 3-butenyloxy group, a 3-butynyloxy group, a methylthio group, an ethylthio group, or a 2-propenylthio group; ⁷ Represents 1-methylethyl group or 1-methylpropyl group, X ⁸ Represents a 2-methylphenyl group or a 2,6-dichlorophenyl group. ]
A pyrazolinone compound represented by:
Examples of the active ingredient of such an insecticide include the following.
(1) Organophosphorus insecticidal compound
Acetate, Aluminum phosphide, Butathiofos, Cadusafos, Chlorethoxyphos, Chlorfenvinphos, Chlorpyriphos , Cyanophos (CYAP), diazinon, DCIP (dichloropropionic ether), diclofenthion (ECP), dichlorvos (DDVP), dimethoate (dimethoa) e), dimethylvinphos, disulfoton, EPN, ethion, ethophos, etrimfos, fenthion: MPP, phenothiothion, EP , Formothion, hydrogen phosphide, isofenphos, isoxathion, malathion, mesulfenfos, methidathione monochromate, TP rotophos, naled (BRP), oxydeprofos (ESP), parathion, fosarone, phosmet (PMP), pirimiphos-methyl, pyridenethiop quinalphos), phentoate (PAP), profenofos, propopafos, prothiofos, pyrachlorfos, salithion, sulprofos, sulprofos Temefos, tetrachlorvinphos, terbufos, thiomethon, trichlorphon (DEP), bamidithione, folate, etc .;
(2) Carbamate insecticidal active compound
Aranicarb, bendiocarb, benfuracarb, BPMC, carbaryl, carbofuran, carbosulfane, cloethocarb, cloethocarb , Phenothiocarb, phenoxycarb, furathiocarb, isoprocarb (MIPC), metocarb, methomyl, meNiocarb, methiocarb, Oxamyl (oxamyl), pirimicarb (pirimicarb), propoxur (propoxur: PHC), XMC, thiodicarb (thiodicarb), xylylcarb (xylylcarb), aldicarb (aldicarb) or the like;
(3) Synthetic pyrethroid insecticidal compound
Acrinathrin, allethrin, benfluthrin, beta-cyfluthrin, bifenthrin, cycloprothrin, cyfluthrin, cyfluthrin (cy). ), Deltamethrin, esfenvalerate, ethofenprox, fenpropathrin, fenvalerate, flucitrinate , Flufenprox, flumethrin, fluvalinate, halfenprox, imiprothrin, permethrin, praretrin, piletrethrin, palletrin. , Sigma-cypermethrin, silafluofen, tefluthrin, tralomethrin, transfluthrin, tetramethrin, tetramethrin. Phenothrin, cyphenothrin, alpha-cypermethrin, zeta-permethrin, lambda-cyhalothrin, urmethaurine, framethrin, urmeturin fluvalinate), 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl (EZ)-(1RS, 3RS; 1RS, 3SR) -2,2-dimethyl-3-prop-1-enylcyclopropane Carboxylate, 2,3,5,6-tetrafluoro-4-methylbenzyl (EZ)-(1RS, 3RS; 1RS, 3SR) -2,2-dimethyl-3-prop-1-enyl Cyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl (1RS, 3RS; 1RS, 3SR) -2,2-dimethyl-3- (2-methyl-1-propenyl) Cyclopropanecarboxylate and the like;
(4) Nereistoxin insecticidal compound
Cartap, bensultap, thiocyclam, monosultap, bisultap, etc .;
(5) Neonicotinoid insecticidal active compound
Imidacloprid, nitenpyram, acetamiprid, thiamethoxam, thiacloprid, dinotefuran, lothianidin, lothianidine, etc.
(6) Benzoylurea insecticidal active compound
Chlorfluazuron, bistrifluron, diafenthiuron, diflubenzuron, fluazuron, flucycloxuron, flucycloxuron, flucycloxuron, flucycloxuron, flucycloxuron, flucycloxuron, flucycloxuron, flucycloxuron, flucycloxuron Mufluron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, triazuron, etc .;
(7) Phenylpyrazole insecticidal compound
Acetoprole, etiprole, fipronil, vaniliprole, pyriprole, pyrafluprole, etc .;
(8) Bt toxin
Live spores and produced crystal toxins from Bacillus thuringiensis, and mixtures thereof;
(9) Hydrazine insecticidal compound
Chromafenozide, halofenozide, methoxyphenozide, tebufenozide and the like;
(10) Organochlorine compounds
Aldrin, dieldrin, dienochlor, endosulfan, methoxychlor and the like;
(11) Other insecticidal active ingredients
Machine oil, nicotine-sulfate;
Avermectin (vermectin-B), bromopropyrate, buprofezin, chlorphenapyr, cyromazine, D-D (1,3-Dichloropropene, D-D (1,3-Dichloropropene) fenazaquin, flupyrazofos, hydroprene, metoprene, indoxacarb, methoxadiazone, milbemycine, milbemycine , Pyridalyl, pyriproxyfen, spinosad, sulfuramide, tolfenpyrad, triazemid, flubendiamide, flubendiamide ), Benclothiaz, Calcium cyanoamide, Calcium polysulfide, Chlorden, DDT, DSP, flufenerim, flunicam flu en), formatenate, metham-ammonium, metham-sodium, methyl bromide, ninototefuran, potassium oleate (potassium proleole) Butto (protrifenbute), spiromesifen (spiromesifen), sulfur (Sulfur), metaflumizone (spiratetrazone), pyrifluinazone (pirifluquinone), spinetoram (spiretranol) le),
Formula (11)

[Where:
R ₁₀ Is Me, Cl, Br or F,
R ₂₀ Is F, Cl, Br, C1-C4 haloalkyl, or C1-C4 haloalkoxy,
R ₃₀ Is F, Cl or Br,
R ₄₀ Is H, one or more halogens; CN; SMe; S (O) Me; S (O) ₂ C1-C4 alkyl, C3-C4 alkenyl, C3-C4 alkynyl, or C3-C5 cycloalkylalkyl optionally substituted with Me and OMe,
R ₅₀ Is H or Me,
R ₆₀ H, F or Cl,
R ₇₀ Represents H, F or Cl. A compound represented by
Formula (12)

[Wherein X represents Cl, Br, or I. ]
A compound represented by
Examples of the active ingredient of such an acaricide include, for example, acequinocyl, amitraz, benzoximate, bifenate, phenisobromolate, quinomethionate, chinomethionate, chlorobenzilate, CPCBS (chlorfenson), clofentezine, cyflumetofen, quercene, dioxol, etoxazole, fenbutatin phenothiophene Fenpyroximate, fluacrylpyrim, fluproxyfen, penthiridinepirpene, fenpyridine , Tetradiphon, spirodiclofen, spiromesifen, spirotetramat, amidoflumet, cienopyrafene ), And the like.
Examples of the active ingredient of the nematicide include DCIP, fostiazate, levamisole hydrochloride, methylisothiocyanate, morantartrate tartrate, and imiciafos.
Examples of the active ingredient of such a plant growth regulator include etephon, chlormequat-chloride, mepiquat-chloride, and the like.
The plant disease control agent of the present invention can be used, for example, in agricultural lands such as fields, paddy fields, lawns, orchards. Examples of the “crop” in which the plant disease control agent of the present invention can be used include the following.
Agricultural crops: corn, rice, wheat, barley, rye, oats, sorghum, cotton, soybeans, peanuts, buckwheat, sugar beet, rapeseed, sunflower, sugarcane, tobacco, vegetables, solanaceous vegetables (eggplants, tomatoes, peppers, peppers, potatoes) Cucumber, pumpkin, zucchini, watermelon, melon, etc., cruciferous vegetables (radish, turnip, horseradish, kohlrabi, cabbage, cabbage, mustard, broccoli, cauliflower, etc.), asteraceae (burdock, Shungiku, artichokes, lettuce, etc.), liliaceae vegetables (leek, onion, garlic, asparagus), celeryaceae vegetables (carrot, parsley, celery, red pepper, etc.), red crustacean vegetables (spinach, chard, etc.) (Perilla, mint, basil ), Strawberry, sweet potato, yam, taro, Jatropha, etc.,
Bridegroom,
Foliage plant,
Fruit trees; pears (apples, pears, Japanese pears, quince, quince, etc.), nuclear fruits (peaches, plums, nectarines, ume, sweet cherry, apricots, prunes, etc.), citrus (satsuma mandarin, orange, lemon, lime, grapefruit) ), Nuts (chestnut, walnut, hazel, almond, pistachio, cashew nut, macadamia nut, etc.), berries (blueberry, cranberry, blackberry, raspberry, etc.), grape, oyster, olive, loquat, banana, coffee, Date palm, coconut palm, etc.
Trees other than fruit trees: Cha, mulberry, flowering trees, street trees (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak, poplar, redwood, fu, sycamore, zelkova, black bean, peach tree, Tsuga, rat, pine, Spruce, yew) etc.
“Crop” also includes genetically modified crops.
Examples of plant diseases in which the compound of the present invention or a salt thereof is effective include plant diseases caused by filamentous fungi, and specific examples include the following plant diseases.
Rice blast (Magnaporthe grisea), sesame leaf blight (Cochliobolus miyabeanus), blight (Rhizoctonia solani), idiot seedling (Gibberella fujikuri);
Wheat diseases: powdery mildew (Erysiphe graminis), red mold disease (Fusarium graminearum, F. avenacerum, F. culmorum, Microdochium nivare), rust (Puccinia striformi. (Microlectriella nivale), Snow rot microspora nuclear disease (Typhula sp.), Bare smut (Ustilago tritici), Tuna scab (Pseudocercosporella herposis), Blight (Stagonospora nodorum), macular disease (Pyrenophora tritici-repentis);
Diseases of barley: powdery mildew (Erysiphe graminis), red mold disease (Fusarium graminearum, F. avenacerum, F. culmorum, Microdochium nivare), rust (Puccinia striformi. Ustilago nuda), cloud disease (Rhynchosporium secalis), reticular disease (Pyrenophora teres), spot disease (Cochliobolus sativus), leafy leaf disease (Pyrenophora graminea)
Citrus black spot (Diaporthe citri), scab (Elsinoe fawceti), fruit rot (Penicillium digitatum, P. italicum), Phytophthora parasitica, Phytophthora
Apple Moniria disease (Valsa ceratosperma), powdery mildew (Podosphaera leucotrica), spotted leaf disease (Alternaria alternata apple disease), black spot disease (Alternaria alternata apple disease) (Phytophotocatarum);
Pear black spot (Venturia nashicola, V. pilina), black spot (Alternaria alternata Japan pair pathotype), red scab (Gymnosporangium haraaeum);
Peach ash scab (Monilinia fracticola), black scab (Cladosporium carpophilum), Phomopsis spoilage (Phomopsis sp.);
Grapes black rot (Elsinoe ampelina), late rot (Glomerella gingulata), powdery mildew (Uncinula apelopidis), black rot (Guignardia olividid)
Oyster anthracnose (Gloeosporium kaki), deciduous leaf disease (Cercospora kaki, Mycosphaerella nawae);
Colletotrichum lagenarium, powdery mildew (Sphaerotheca fuligenea), vine blight (Mycosphaerella meloniis), tsuba disease (Fusium oxysporum), psoriasis (Puso) Seedling blight (Pythium sp.);
Tomato ring rot (Alternaria solani), leaf mold (Cladosporium fulvum), plague (Phytophthora infestans);
Eggplant brown spot (Phomopsis vexans), powdery mildew (Erysiphe cichoacearum);
Brassicaceae vegetable black spot (Alternaria japonica), white spot (Cercosporella brassicae);
Leek rust (Puccinia allii), soybean purpura (Cercospora kikuchii), black scab (Elsinoe glycycines), black spot (Diaporthe pororirum var, sojae), rust ps
Green Bean Anthracnose (Colletotrichum lindemthianum)
Peanut black astringency (Cercospora personata), brown spot (Cercospora arachidicola), white silkworm (Sclerotium rolfsii);
Pea powdery mildew (Erysiphe pisi);
Potato summer plague (Alternaria solani), plague (Phytophthora infestans), Scarlet rot (Phytophthora erythroseptica), half body wilt (Verticillium albo-atrum, V. dahenli;
Strawberry powdery mildew (Sphaerotheca humuli);
Tea net blast (Exobasidium reticulatum); white scab (Elsinoe leucospila), ring spot disease (Pestarotropis sp.), Anthracnose (Colletotrichum theae-sinensis)
Tobacco red leaf disease (Alternaria longipes), powdery mildew (Erysiphe cichoracearum), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina), plague (Phytophathorophora)
Sugar beet brown spot (Cercospora beticola), leaf rot (Thanatephorus cucumeris), root rot (Thanatephorus cucumeris), black root (Aphanomyces cochlioides);
Rose scab (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa);
Chrysanthemum brown spot (Septoria chrysanthemi-indici), white rust (Puccinia horiana);
Sunflower downy mildew (Plasmopara halstedii);
Onion white spot blight (Botrytis cinerea, B. byssidea, B. squamosa), gray rot (Botrytis alli), sclerotia rot (Botrytis squamosa);
Various crops of gray mold disease (Botrytis cinerea), sclerotia sclerotia, seedling blight caused by Pythium spp. (Pythium aphanidermatum, P. debarianum, P. Black soot disease (Alternaria brassicicola);
Shiva dollar spot disease (Sclerotinia homeocarpa), brown patch disease and large patch disease (Rhizotonia solani);
Banana sigatoka disease (Mycosphaerella fijiensis, Mycosphaerella musicola, Pseudocercospora musae); and
Viral diseases of various plants mediated by Polymixa spp. Or Olpidium spp.

Hereinafter, although this invention is demonstrated in more detail by a manufacture example, a formulation example, a test example, etc., this invention is not limited only to these examples.
First, the manufacture example of this invention compound is shown.
Production Example 1

To a mixture of 0.30 g of 2-amino-thiazole-5-carboxylic acid, 2 mL of DMF, 0.42 g of triethylamine and 0.65 g of 2-chloro-N-methylbenzylamine, 1.10 g of BOP reagent was added and stirred at room temperature overnight. . The reaction mixture was poured into ice water and the resulting crystals were collected by filtration. The obtained crystallized crystals were washed with saturated aqueous sodium hydrogen carbonate, water and ethyl acetate to give 2-amino-N- (2-chlorobenzyl) -N-methyl-thiazole-5-carboxylic acid amide (hereinafter referred to as the present compound (1). 0.26 g was obtained.
¹ H-NMR (DMSO-d ₆ ) δ [ppm]: 3.13 (3H, s), 4.72 (2H, s), 7.22-7.52 (7H, m)
Production Example 2

To a mixture of 1.34 g of 2-amino-4-chloro-thiazole-5-carboxylic acid, 30 mL of DMF, 0.50 g of triethylamine and 2.21 g of BOP reagent, 0.20 g of 2-chloro-4-fluoro-N-methyl-benzylamine was added. 87 g was added and stirred at room temperature for 3 hours. The reaction mixture was poured into ice water and extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2-amino-4-chloro-N- (2-chloro-4-fluorobenzyl) -N-methyl-thiazole-5-carboxylic acid amide (hereinafter referred to as the present product). 0.90 g of Inventive Compound (2)) was obtained.
¹ H-NMR (CDCl ₃ ) δ: 3.04 (3H, s), 4.78 (2H, s), 5.33 (2H, s), 7.00 (1H, td, J = 8.27) , 2.50 Hz), 7.15 (1H, dd, J = 8.33, 2.78 Hz), 7.34-7.29 (1H, m),
Production Example 3

2-aminothiazole-5-carboxylic acid 0.29 g, DMF 3 mL, triethylamine 0.24 g, BOP reagent 1.06 g, and 2-chloro-4-fluoro-N-methylbenzylamine 0.35 g were mixed, and the mixture was Stir at room temperature for 1 hour. The reaction mixture was poured into ice water and extracted with ethyl acetate. The extract was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2-amino-N- (2-chloro-4-fluorobenzyl) -N-methylthiazole-5-carboxylic acid amide (hereinafter referred to as the present compound (3)). 0.37 g was obtained.
¹ H-NMR (DMSO-D ₆ ) δ: 3.12 (3H, s), 4.68 (2H, s), 7.22-7.31 (2H, m), 7.38 (1H, s ), 7.50 (1H, dd, J = 8.8, 2.4 Hz), 7.53 (2H, s).
Production Example 4

A mixture of 0.32 g of 2-amino-4-methylthiazole-5-carboxylic acid, 3 mL of DMF, 0.24 g of triethylamine, 1.06 g of BOP reagent, and 0.35 g of 2-chloro-4-fluoro-N-methylbenzylamine was mixed. The mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into ice water and extracted with ethyl acetate. The extract was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2-amino-N- (2-chloro-4-fluorobenzyl) -4-methyl-N-methylthiazole-5-carboxylic acid amide (hereinafter referred to as the present invention). 0.29 g of compound (4) is obtained.
¹ H-NMR (DMSO-D ₆ ) δ: 2.13 (3H, s), 2.89 (3H, s), 4.63 (2H, s), 7.24-7.30 (3H, m ), 7.32-7.36 (1H, m), 7.49 (1H, dd, J = 8.8, 2.7 Hz).
Production Example 5

0.42 g of 2-amino-4-trifluoromethylthiazole-5-carboxylic acid, 3 mL of DMF, 0.24 g of triethylamine, 1.06 g of BOP reagent, and 0.35 g of 2-chloro-4-fluoro-N-methylbenzylamine Mix and stir the mixture for 1 hour at room temperature. The reaction mixture was poured into ice water and extracted with ethyl acetate. The extract was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography to give 2-amino-N- (2-chloro-4-fluorobenzyl) -N-methyl-4-trifluoromethylthiazole-5-carboxylic acid amide (hereinafter, 0.45 g of the present compound (5) was obtained.
¹ H-NMR (DMSO-D ₆ ) δ: 2.88 (3H, s), 4.66 (2H, s), 7.26-7.35 (2H, m), 7.50 (1H, dd) , J = 8.8, 2.4 Hz), 7.73 (2H, s).
Reference production example 1
To 400 ml of sulfolane dehydrated azeotropically with 100 ml of n-heptane, 52.3 g of potassium fluoride and 100 ml of n-heptane were added and azeotropically dehydrated for 1 hour. The reaction mixture was cooled to room temperature. To this, 92.4 g of 2,4-dichlorothiazole was added and stirred at 180 ° C. for 5 hours. The reaction mixture was cooled to room temperature and distilled under reduced pressure to obtain 62.5 g of 4-chloro-2-fluorothiazole.
4-chloro-2-fluorothiazole

¹ H-NMR (CDCl ₃ ) δ: 6.72 (1H, s)
Reference production example 2
10.7 g of diisopropylamine was dissolved in 200 ml of tetrahydrofuran and cooled to -70 ° C. Here, 64 ml of n-butyllithium (1.65 mol / L) was dropped, and the temperature was raised to 0 ° C. The mixture was again cooled to -70 ° C, and 30 ml of a tetrahydrofuran solution containing 13.2 g of 4-chloro-2-fluorothiazole was added dropwise. After incubating at -70 ° C for 3 hours, finely crushed dry ice was added, followed by stirring at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and ethyl acetate and 10% sulfuric acid were added to the resulting solid for liquid separation. The organic layer was washed with water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to give 13.5 g of 4-chloro-2-fluorothiazole-5-carboxylic acid.
4-chloro-2-fluorothiazole-5-carboxylic acid

¹ H-NMR (DMSO-d ₆ ) δ: 4.14 (1H, s)
Reference production example 3
30 ml of 28% aqueous ammonia solution was cooled to 0 ° C., and 3.63 g of 4-chloro-2-fluorothiazole-5-carboxylic acid was added in several portions. The mixture was stirred overnight at room temperature and 10% sulfuric acid was added dropwise until a solid formed. The resulting solid was filtered and dried to obtain 3.10 g of 2-amino-4-chlorothiazole-5-carboxylic acid.
2-Amino-4-chlorothiazole-5-carboxylic acid

¹ H-NMR (DMSO-d ₆ ) δ: 7.20 (1H, brs), 8.04 (2H, s)
Next, formulation examples are shown. In addition, a part shows a weight part.
Formulation Example 1
A wettable powder is obtained by thoroughly pulverizing and mixing 50 parts of any of the compounds (1) to (5) of the present invention, 3 parts of calcium lignin sulfonate, 2 parts of magnesium lauryl sulfate, and 45 parts of synthetic silicon hydroxide.
Formulation Example 2
20 parts of any one of the compounds (1) to (5) of the present invention and 1.5 parts of sorbitan trioleate are mixed with 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol and finely pulverized by a wet pulverization method. Thereafter, 40 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added to this, and 10 parts of propylene glycol is further added and stirred to obtain a flowable preparation.
Formulation Example 3
A powder is obtained by thoroughly pulverizing and mixing any 2 parts of the compounds (1) to (5) of the present invention, 88 parts of kaolin clay and 10 parts of talc.
Formulation Example 4
An emulsion is obtained by thoroughly mixing 5 parts of any one of the compounds (1) to (5) of the present invention, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 75 parts of xylene.
Formulation Example 5
Any 2 parts of the compounds (1) to (5) of the present invention, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay may be mixed well, and then water may be added. A granule is obtained by kneading and granulating and drying.
Formulation Example 6
By mixing 10 parts of any one of the compounds (1) to (5) of the present invention; 35 parts of white carbon containing 50 parts of polyoxyethylene alkyl ether sulfate ammonium salt; and 55 parts of water, and finely pulverizing them by a wet pulverization method. Get a flowable formulation.
Formulation Example 7
40 parts of any of the compounds (1) to (5) of the present invention, 5 parts of propylene glycol (manufactured by Nacalai Tesque), 5 parts of Soprophor FLK (manufactured by Rhodia Nikka), and 0.2 part of anti-form C emulsion (Dow) Corning), 0.3 part of Proxel GXL (manufactured by Arch Chemical), and 49.5 parts of ion-exchanged water are mixed to prepare a base slurry. 150 parts of glass beads (Φ = 1 mm) are added to 100 parts of the slurry, and pulverized for 2 hours while cooling with cooling water. After grinding, the glass beads are removed by filtration to obtain a flowable formulation.
Formulation Example 8
50 parts of any one of the present compounds (1) to (5), 38.5 parts of NN kaolin clay (manufactured by Takehara Chemical Industries), 10 parts of Morwet D425, 1.5 parts of Morwer EFW (manufactured by Akzo Nobel) And the mixture is pulverized with a jet mill to obtain a powder.
Next, test examples show that the compounds of the present invention are useful for controlling plant diseases.
The control effect is obtained by visually observing the area of the lesion on the test plant at the time of the survey, and comparing the area of the lesion on the plant treated with the compound of the present invention and the area of the lesion on the untreated plant. evaluated.
Test example 1
The plastic pot was filled with soil, tomato (variety: patio) was sown and grown in a greenhouse for 20 days. Each of the compounds (1), (2), (3) and (4) of the present invention is made into a flowable formulation according to Formulation Example 6, and then diluted with water to a predetermined concentration (500 ppm). The foliage was sprayed so as to adhere well. After air-drying the diluted solution on the leaf surface to dryness, an aqueous suspension of Phytophthora infestans spores was spray-inoculated. After inoculation, the plant was first placed at 23 ° C. under high humidity for 1 day, and then cultivated in an artificial climate room at 20 ° C. for 4 days.
The lesion area in the plant which processed this invention compound (1), (2), (3) and (4) was 30% or less of the lesion area in an untreated plant.
Test example 2
Tomato (variety: patio) was sown on a plastic sponge piece and hydroponically cultivated in a plastic cup for about 20 days. Each compound of the present invention (1), (2), (3) and (4) is made into a flowable formulation according to Formulation Example 6, and then 1 mg per plant in a cup of the above-mentioned tomato hydroponics seedling in terms of weight. It was thrown into. Further, after hydroponics for 7 days, an aqueous suspension of Phytophthora infestans spores was spray-inoculated. After inoculation, the plant was first placed at 23 ° C. under high humidity for 1 day, and then cultivated in an artificial climate room at 20 ° C. for 4 days.
The lesion area in the plant which processed this invention compound (1), (2), (3) and (4) was 30% or less of the lesion area in an untreated plant.
Test example 3
A plastic pot was filled with soil, seeded with wheat (variety: Shirogane), grown in a greenhouse for 9 days, and then sprinkled with spores of wheat red rust fungus (Puccinia redondota f. Sp. Tritici). After inoculation, it was placed in a dark and humid place at 23 ° C. for 1 day, and then air-dried to obtain a wheat rust-infected seedling. The compound (2) of the present invention was made into a flowable formulation according to Formulation Example 6, diluted with water to a predetermined concentration (500 ppm), and sprayed on the foliage so that it sufficiently adhered to the leaf surface of the wheat. After spraying, the plants were air-dried and placed under illumination for 6 days, and then the lesion area was examined. As a result, the lesion area in the plant treated with the compound (2) of the present invention was 30% or less of the lesion area in the untreated plant.
Test example 4
The plastic pot was filled with soil, cucumber (variety: Sagamihanjiro) was sown and grown in a greenhouse for 12 days. The above-mentioned pot was spray-inoculated with an aqueous suspension of Pseudoperonospora cubis zoosporangium, placed at 23 ° C. under high humidity for 1 day, and then air-dried to obtain a cucumber downy mildew-infected seedling. Each of the compounds (2), (3) and (4) of the present invention is made into a flowable formulation according to Formulation Example 6 and then diluted with water to a predetermined concentration (500 ppm) so that it sufficiently adheres to the cucumber leaf surface. The foliage was sprayed. After spraying, the plants were air-dried and placed in a greenhouse at 23 ° C. for 5 days, and then the lesion area was examined. As a result, the lesion area in the plant which processed this invention compound (2), (3) and (4) was 30% or less of the lesion area in an untreated plant.

The compound of the present invention or a salt thereof is useful for plant disease control because it has an excellent plant disease control effect.

Claims (10)

1. Formula (1)
   

   

   [Where,
   R ¹ is hydrogen, halogen, cyano group, nitro group, —O—R ⁴ group, —S—R ⁴ group, —S (═O) —R ⁴ group, —S (═O) ₂ —R ⁴ group, Represents a C1-C5 chain hydrocarbon group or C3-C5 cycloalkyl group optionally substituted with one or more groups selected from group B;
   p represents any integer from 1 to 5;
   R ² is a C1-C5 chain hydrocarbon group which may be substituted with one or more groups selected from group C, and a C3-C10 cycloalkyl group which may be substituted with one or more groups selected from group D , Phenyl group, halogen, cyano group, nitro group, —O—R ⁵ group, —S—R ⁵ group, —C (═O) —R optionally substituted with one or more groups selected from group E ⁵ groups, —C (═O) —OR ⁵ groups, —OC (═O) —R ⁵ groups, —NR ⁵ R ⁶ groups, —C (═O) —NR ⁵ R ⁶ groups or —NR ⁵ —C (= O) —R ⁶ group is represented,
   Alternatively, when p is 2 or more and two R ² are bonded to adjacent carbons of the benzene ring, the two R ² are bonded and substituted with one or more groups selected from group E. An optionally substituted C2-C5 polymethylene group, a propene-1,3-diyl group optionally substituted with one or more groups selected from group E, and one or more groups selected from group E. Represents a 1,3-butadiene-1,4-diyl group or a methylenedioxy group,
   R ³ is a C1-C5 chain hydrocarbon group which may be substituted with one or more groups selected from group C or a C3-C10 cycloalkyl group which may be substituted with one or more groups selected from group D Represents
   R ⁴ represents a C1-C4 chain hydrocarbon group,
   R ⁵ and R ⁶ are the same or different from each other, and are hydrogen, a C1 to C10 chain hydrocarbon group optionally substituted with one or more groups selected from group C, and one or more groups selected from group D. A C3-C10 cycloalkyl group which may be substituted or a phenyl group which may be substituted with one or more groups selected from group E.
   However, when p is any integer of 2 to 5, R ² is the same or different from each other.
   Group B represents a group consisting of halogen, cyano group, C1-C4 alkoxy group, C1-C4 alkylthio group, C1-C4 alkylsulfinyl group and C1-C4 alkylsulfonyl group,
   Group C is a C3-C10 cycloalkyl group optionally substituted with one or more groups selected from Group D, a halogen, a cyano group, a C1-C4 alkoxy group optionally substituted with halogen, and a halogen-substituted group An optionally substituted C1-C4 alkylthio group, an optionally substituted C1-C4 alkylsulfinyl group, an optionally substituted C1-C4 alkylsulfonyl group, optionally substituted with a halogen (C1- C4 alkyl) represents a group consisting of a carbonyl group, a (C1-C4 alkoxy) carbonyl group optionally substituted with halogen, and a (C1-C4 alkyl) carbonyloxy group optionally substituted with halogen,
   Group D represents a group consisting of a C1-C5 alkyl group and halogen,
   Group E is halogen, cyano group, nitro group, C1-C10 chain hydrocarbon group optionally substituted with halogen, C3-C10 cycloalkyl group optionally substituted with one or more groups selected from group D C1-C4 alkoxy group optionally substituted with halogen, C1-C4 alkylthio group optionally substituted with halogen, C1-C4 alkylsulfinyl group optionally substituted with halogen, halogen-substituted May be a C1-C4 alkylsulfonyl group, a (C1-C4 alkyl) carbonyl group optionally substituted with halogen, a (C1-C4 alkoxy) carbonyl group optionally substituted with halogen, and a halogen-substituted Represents a group of good (C1-C4 alkyl) carbonyloxy groups. ]
   Or an salt thereof.
2. The amide compound or a salt thereof according to claim 1, wherein R ² is halogen.
3. The amide compound or a salt thereof according to claim 1, wherein R ² is fluorine or chlorine.
4. The amide compound or a salt thereof according to claim 1, wherein R ² is fluorine or bromine.
5. The amide compound or a salt thereof according to claim 1, wherein p is 3, and R ² is the same or different from each other and is halogen.
6. The amide compound or a salt thereof according to claim 1, wherein p is 3, and R ² are the same or different from each other and are fluorine or chlorine.
7. The amide compound or a salt thereof according to claim 1, wherein p is 3, and R ² is the same or different from each other and is fluorine or bromine.
8. A plant disease control agent comprising the amide compound or a salt thereof according to claim 1 and an inert carrier.
9. A method for controlling plant diseases comprising a step of applying an effective amount of the amide compound or a salt thereof according to claim 1 to a plant or a soil in which the plant grows.
10. Use of the amide compound or a salt thereof according to claim 1 for controlling plant diseases.