WO2010134628A1 - Composé amide et son utilisation pour la lutte contre les maladies des plantes - Google Patents

Composé amide et son utilisation pour la lutte contre les maladies des plantes Download PDF

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WO2010134628A1
WO2010134628A1 PCT/JP2010/058856 JP2010058856W WO2010134628A1 WO 2010134628 A1 WO2010134628 A1 WO 2010134628A1 JP 2010058856 W JP2010058856 W JP 2010058856W WO 2010134628 A1 WO2010134628 A1 WO 2010134628A1
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group
halogen
carboxylic acid
optionally substituted
amino
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PCT/JP2010/058856
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English (en)
Japanese (ja)
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有本翔
大平大輔
久保田真由美
倉橋真
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住友化学株式会社
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Publication of WO2010134628A1 publication Critical patent/WO2010134628A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles

Definitions

  • the present invention relates to an amide compound and its use for controlling plant diseases.
  • An object of the present invention is to provide 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.
  • 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, A methyl group substituted with one or more groups selected from group A, a C2-C5 chain hydrocarbon group optionally substituted with one or more groups selected from group B, a C3-C5 cycloalkyl group, fluoromethyl Represents a group or a difluoromethyl group, p represents any integer from 0 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 ( ⁇
  • R 5 and R 6 are independently hydrogen, a C1-C10 chain hydrocarbon group which may be substituted with one or more groups selected from group C, and one or more groups selected from group D.
  • R 2 may be the same as or different from each other.
  • Group A represents a group consisting of chlorine, bromine, iodine, cyano group, C1-C4 alkoxy group, C1-C4 alkylthio group, C1-C4 alkylsulfinyl group and C1-C4 alkylsulfonyl group
  • 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, or a halogen-substituted group
  • an salt thereof (hereinafter referred to as the present compound).
  • R 1 is hydrogen and R 2 is fluorine or bromine.
  • a plant disease control agent comprising the amide compound or salt thereof according to any one of [1] to [10] and an inert carrier.
  • 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 [10] to a plant or soil where the plant grows.
  • Halogen means fluorine, chlorine, bromine and iodine.
  • methyl group substituted with one or more groups selected from group A include, for example, chloromethyl group, dichloromethyl group, trichloromethyl group, bromomethyl group, dibromomethyl group, iodomethyl group, cyanomethyl group, dicyanomethyl group, Methoxymethyl group, ethoxymethyl group, propoxymethyl group, isopropoxymethyl group, butoxymethyl group, isobutoxymethyl group, t-butoxymethyl group, methylthiomethyl group, ethylthiomethyl group, propylthiomethyl group, isopropylthiomethyl group Butylthiomethyl group, isobutylthiomethyl group, t-butylthiomethyl group, methanesulfinylmethyl group, ethanesulfinylmethyl group, propanesulfiny
  • Examples of the “C2-C5 chain hydrocarbon group optionally substituted with one or more groups selected from group B” include, for example, an ethyl group, a 2-fluoroethyl group, a 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
  • 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-chlor
  • C3-C10 cycloalkyl group optionally substituted with one or more groups selected from group D examples include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, cyclononyl.
  • 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, 4-methyl
  • phenyl group optionally substituted with one or more groups selected from group E examples 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-propylphenyl 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.
  • propene-1,3-diyl group optionally substituted with one or more groups selected from group E examples 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-methoxyprop
  • 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,
  • C1-C4 chain hydrocarbon group examples 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-triflu
  • 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.
  • C1-C4 alkylsulfinyl group examples include a methanesulfinyl group, an ethanesulfinyl group, a propanesulfinyl group, an isopropanesulfinyl group, a butanesulfinyl group, an isobutanesulfinyl group, and a t-butanesulfinyl group.
  • C1-C4 alkylsulfonyl group examples 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.
  • 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.
  • C1-C4 alkylsulfinyl group optionally substituted with halogen examples 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, isopropanesulfin
  • 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, isopropanesulfony
  • 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-
  • 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.
  • 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, Butano
  • C1-C5 alkyl group examples 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′-hexa
  • R 1 Is hydrogen, halogen, cyano group, methyl group substituted with one or more groups selected from group A, C2-C5 chain hydrocarbon group optionally substituted with one or more groups selected from group B, fluoro An amide compound which is a methyl group or a difluoromethyl group;
  • R 1 Is hydrogen, halogen, a methyl group substituted with one or more groups selected from group A, a C2-C5 chain hydrocarbon group optionally substituted with one or more groups selected from group B, a fluoromethyl group, or An amide compound which is a difluoromethyl group;
  • formula (1) R 1 Is hydrogen, halogen, cyano group, methyl group substituted with one or more groups selected from group A,
  • the compound of the present invention or a salt thereof can be produced by reacting compound (3) or a salt thereof with compound (2) in the presence of a dehydration condensing agent.
  • a dehydration condensing agent [In the formula, R 1 , R 2 And p represent the same meaning as described above. ] The reaction is usually performed in the presence of a solvent.
  • 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.
  • THF tetrahydrofuran
  • MTBE tert-butyl methyl ether
  • hexane Aliphatic hydrocarbons such as
  • 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.
  • WSC 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride
  • benzotriazol-1-yloxy) tris dimethylamino) phosphonium hexa
  • BOP reagent fluorophosphate
  • 1,3-dicyclohexylcarbodiimide 1,3-dicyclohexylcarbodiimide.
  • 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.
  • a BOP reagent when used, the reaction is performed in the presence of a base as necessary.
  • bases include tertiary amines such as triethylamine and diisopropylethylamine, and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine.
  • the base is usually used at a ratio of 1 to 10 mol per 1 mol of the compound (2).
  • 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.
  • 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 And p represent the same meaning as described above. ] The reaction is usually performed in the presence of a solvent.
  • solvent used in the reaction examples 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.
  • 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.
  • the compound (3) is usually used in a proportion of 1 to 3 mol
  • 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.
  • 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.
  • 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.
  • solvent used in the reaction examples 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.
  • Examples of the dehydrating condensing agent used in the reaction include WSC, BOP reagent, and 1,3-dicyclohexylcarbodiimide.
  • the compound (3) is usually used in a proportion of 1 to 3 mol
  • 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.
  • the reaction when a BOP reagent is used, the reaction is performed in the presence of a base as necessary.
  • the base examples include tertiary amines such as triethylamine and diisopropylethylamine, and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine.
  • the base is usually used at a ratio of 1 to 10 mol per 1 mol of the compound (5).
  • 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 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, acetones, ketones such as methyl ethyl ketone and 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.
  • 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.
  • 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 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.
  • 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.
  • 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.
  • 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.
  • a surfactant and other formulation adjuvants 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%.
  • 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).
  • liquid carrier examples 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
  • gaseous carrier examples include dimethyl ether and carbon dioxide.
  • surfactant examples 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.
  • 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 sugars, 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.
  • fixing agents eg starch, arabic gum, cellulose derivatives, Alginic acid
  • lignin derivatives lignin derivatives
  • bentonite sugars synthetic water-soluble polymers (eg
  • 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 cultivated, and a method of applying to the plant seed. It is done.
  • the plant disease control method of the present invention the plant disease control agent of the present invention is usually used.
  • the application amount of the plant disease control agent of the present invention is 1,000 m.
  • the amount of the compound of the present invention or a salt thereof is usually 1 to 500 g, preferably 2 to 200 g.
  • 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.
  • 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.
  • 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.
  • Azole bactericidal active compound Propiconazole, Prothioconazole, Triadimenol, Prochloraz, Penconazole, Dibuconazole, Tebuconazole, 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;
  • Amine fungicidal active compounds Fenpropimorph, tridemorph,
  • a compound represented by Examples of the active ingredient of such an acaricide include acequinocyl, amitraz, benzoximate, bifenate, phenobromolate, quinomethionate, and chinomethionate.
  • chlorobenzilate CPCBS (chlorfenson), clofentezine, cyflumetofen, quercene, dioxol, etoxazole, fenbutatin phenothiophene Fenpyroximate, fluacrylpyrim, fluproxyfen, penthiridinepirpene, fenpyridine , Tetradiphon, spirodiclofen, spiromesifen, spirotetramat, amidoflumet, cenopyrofene ), 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,
  • 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.
  • 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.
  • 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-arum, re.
  • 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); Chrysant
  • 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.
  • 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 solid was washed with t-butyl methyl ether, and 2-amino-N- (4-methylbenzyl) -thiazole-5-carboxylic acid amide (hereinafter referred to as the present compound (2)) was reduced to 0. 21 g was obtained.
  • 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-N- (3-methylbenzyl) -thiazole-5-carboxylic acid amide (hereinafter referred to as the present compound (3)) to 0. 10 g was obtained.
  • 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 solid was washed with t-butyl methyl ether, and 2-amino-N- (2-methylbenzyl) -thiazole-5-carboxylic acid amide (hereinafter referred to as the present compound (4)) was reduced to 0. 15 g was obtained.
  • the reaction mixture was poured into aqueous sodium bicarbonate and extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over magnesium sulfate. The mixture was concentrated under reduced pressure, and t-butyl methyl ether and hexane were added to the residue. The crystals were collected by filtration to obtain 0.39 g of 2-amino-N- (2-bromobenzyl) -thiazole-5-carboxylic acid amide (hereinafter referred to as the present compound (10)).
  • the reaction mixture was poured into water and extracted with ethyl acetate.
  • the extract was washed with saturated aqueous sodium hydrogen carbonate and saturated brine, and dried over magnesium sulfate. Concentrated under reduced pressure, and chloroform was added to the residue. After applying ultrasonic waves, the crystals were collected by filtration, and 2-amino-N- (2,3-difluorobenzyl) -thiazole-5-carboxylic acid amide (hereinafter referred to as the present compound (13)) was 0. .36 g was obtained.
  • the reaction mixture was poured into water and extracted with ethyl acetate.
  • the extract was washed with saturated aqueous sodium hydrogen carbonate and saturated brine, and dried over magnesium sulfate. Concentrated under reduced pressure, and chloroform was added to the residue. After applying ultrasonic waves, the crystals were collected by filtration, and 2-amino-N- (2-chloro-4-fluorobenzyl) -thiazole-5-carboxylic acid amide (hereinafter referred to as the present compound (14)). 0.42 g was obtained.
  • 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-N- (3-methoxybenzyl) -thiazole-5-carboxylic acid amide (hereinafter referred to as the present compound (25)) to 0. 19 g was obtained.
  • Production Example 97 A mixture of 0.54 g of 2-amino-4-chlorothiazole-5-carboxylic acid, 3 mL of DMF, 0.20 g of triethylamine, 0.89 g of BOP reagent, and 0.31 g of 3,4-difluoro-2-methylbenzylamine, The mixture was stirred at room temperature for 2 hours. 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.
  • Production Example 99 Mix 0.54 g 2-amino-4-difluoromethylthiazole-5-carboxylic acid, 3 mL DMF, 0.14 g triethylamine, 0.62 g BOP reagent, and 0.22 g 4,5-difluoro-2-methylbenzylamine, The mixture was stirred at room temperature for 3 hours. 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.
  • Production Example 102 Mix 0.78 g of 2-amino-4-difluoromethylthiazole-5-carboxylic acid, 3 mL of DMF, 0.41 g of triethylamine, 0.89 g of BOP reagent, and 0.52 g of 2-bromo-3,5-difluorobenzylamine hydrochloride And the mixture was stirred at room temperature for 3 hours. 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 reaction mixture was poured into ice water and extracted with ethyl acetate.
  • the extract was washed with saturated aqueous sodium hydrogen carbonate and saturated brine, and dried over magnesium sulfate.
  • the mixture was concentrated under reduced pressure, and hexane, t-butyl methyl ether, and ethyl acetate were added to the residue.
  • the crystals were collected by filtration, and 2-amino-N- (2,6-dichlorobenzyl) -thiazole-5-carboxylic acid amide (hereinafter referred to as the present compound (107)) was 0. .32 g was obtained.
  • the reaction mixture was poured into ice water and extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate and saturated brine, and dried over magnesium sulfate. Concentrated under reduced pressure, and chloroform was added to the residue. After applying ultrasonic waves, the crystals were collected by filtration, and 2-amino-N- (2-chloro-6-fluorobenzyl) -thiazole-5-carboxylic acid amide (hereinafter referred to as the present compound (108)). 0.23 g was obtained.
  • the reaction mixture was poured into ice water and extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate and saturated brine, and dried over magnesium sulfate. The mixture was concentrated under reduced pressure, and t-butyl methyl ether and ethyl acetate were added to the residue. After applying ultrasonic waves, the crystals were collected by filtration, and 2-amino-N- (2,3-dimethylbenzyl) -thiazole-5-carboxylic acid amide (hereinafter referred to as the present compound (109)) was 0. .29 g was obtained.
  • the present compound (109) 2-amino-N- (2,3-dimethylbenzyl) -thiazole-5-carboxylic acid amide
  • the mixture was heated and stirred at 80 ° C. for 4 hours.
  • the reaction mixture was allowed to cool to room temperature, hexane was added to the reaction mixture to precipitate a precipitate, the solid was filtered off, and the filtrate was concentrated.
  • To the obtained residue were added 30 ml of EtOH and 2.3 g of thiourea, and the mixture was stirred at 80 ° C. for 2 hours. After allowing to cool to room temperature, 47 ml of 5% NaOH aqueous solution was added to the reaction mixture, and the mixture was stirred at room temperature for 2 hours.
  • the mixture was stirred at room temperature for 3 hours, and 46.4 mL of 4N aqueous sodium hydroxide solution was added.
  • the mixture was stirred at room temperature for 1 hour, and 87.5 mL of 1N hydrochloric acid was added.
  • the reaction mixture was allowed to stand and the THF layer was separated.
  • the aqueous layer was extracted with t-butyl ethyl ether and combined with the THF layer.
  • the extract was washed with water and saturated brine in that order and dried over sodium sulfate. Concentrated under reduced pressure and 5 mL of THF was added to the residue. Under ice-cooling, 1.5 mL of concentrated hydrochloric acid was added, and toluene was added to azeotrope water.
  • reaction mixture was left overnight at room temperature, and 30 mL of aqueous ammonia (28%) was added. The mixture was stirred at room temperature for 3 hours, 94 mL of 4N aqueous sodium hydroxide solution was added, and the mixture was stirred at room temperature for 1 hour. 177 mL of 1N hydrochloric acid was added here.
  • the reaction mixture was allowed to stand and the THF layer was separated. The aqueous layer was extracted with t-butyl ethyl ether and combined with the THF layer. The extract was washed with water and saturated brine in that order and dried over sodium sulfate. Concentrated under reduced pressure and 10 mL of THF was added to the residue.
  • reaction mixture was left at room temperature overnight, and then the reaction mixture was poured into 80 mL of water. The mixture was extracted with t-butyl methyl ether. The organic layer was washed with water and saturated brine in this order. Dried over magnesium sulfate and concentrated under reduced pressure. To the residue was added 100 mL of THF, 7.27 g of triphenylphosphine was added under ice cooling, and the mixture was stirred at room temperature for 1.5 hours. After leaving at room temperature for 3 days, 28 mL of aqueous ammonia (28%) was added and stirred for 3 hours. To the mixture, 94 mL of 4N aqueous sodium hydroxide solution was added and stirred for 1 hour.
  • the reaction mixture was left at room temperature overnight and then concentrated under reduced pressure. Water and ethyl acetate were added to the residue, and the ethyl acetate layer was separated. The aqueous layer was extracted with ethyl acetate and combined with the previous ethyl acetate layer. The extract was washed with saturated brine and dried over magnesium sulfate. After concentration under reduced pressure, the residue was subjected to silica gel column chromatography to obtain 6.603 g of 2-bromo-3,4,5-trifluorobenzyl alcohol.
  • Each wettable powder is obtained by thoroughly pulverizing and mixing 50 parts of any one of the compounds (1) to (111) of the present invention, 3 parts of calcium lignin sulfonate, 2 parts of magnesium lauryl sulfate, and 45 parts of synthetic silicon hydroxide. Get.
  • Formulation Example 2 20 parts of any one of the compounds (1) to (111) 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. After pulverization, 40 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added thereto, and further 10 parts of propylene glycol is added and stirred to obtain each flowable preparation.
  • Formulation Example 3 Each powder agent is obtained by thoroughly crushing and mixing 2 parts of any one of the compounds (1) to (111) of the present invention, 88 parts of kaolin clay and 10 parts of talc.
  • Formulation Example 4 Each emulsion is obtained by thoroughly mixing 5 parts of any one of the compounds (1) to (111) of the present invention, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 75 parts of xylene. Get. Formulation Example 5 After thoroughly mixing 2 parts of any one of the compounds (1) to (111) 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, water is added. Kneaded well and granulated and dried to obtain each granule.
  • Formulation Example 6 10 parts of any one of the compounds (1) to (111) of the present invention; 35 parts of white carbon containing 50 parts of polyoxyethylene alkyl ether sulfate ammonium salt; and 55 parts of water are mixed and pulverized by a wet pulverization method. Thus, each flowable preparation is obtained.
  • Formulation Example 8 50 parts of any one of the compounds (1) to (111) of the present invention, 38.5 parts of NN kaolin clay (manufactured by Takehara Chemical Industry), 10 parts of Morwet D425, 1.5 parts of Morwer EFW (Akzo Nobel) And the mixture is pulverized with a jet mill to obtain each powder.
  • 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 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.
  • Each of the compounds (15), (18), (52), (57), (58), (85), (90) and (97) of the present invention was made into a flowable formulation according to Formulation Example 6, was diluted to a predetermined concentration (500 ppm) and sprayed on the foliage so as to adhere well 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 compounds (15), (18), (52), (57), (58), (85), (90) and (97) of the present invention was untreated. It was 30% or less of the lesion area in the plant.
  • Test example 2 A plastic pot was filled with soil, seeded with wheat (variety: Apogee), and grown in a greenhouse for 10 days. Each of the compounds (2), (9), (18), (40), (43), (52), and (89) of the present invention was made into a flowable formulation according to Formulation Example 6, and then diluted with water. A predetermined concentration (500 ppm) was applied, and the foliage was sprayed so as to sufficiently adhere to the leaf surface of the wheat. After spraying, the plants were air-dried and sprayed and inoculated with an aqueous suspension of Septoria tritici spores after 3 or 4 days. After the inoculation, the area was first placed under a high humidity of 18 ° C.
  • the lesion area in the plant treated with the compounds (2), (9), (18), (40), (43), (52), and (89) of the present invention is the disease in the untreated plant. It was 30% or less of the spot area.
  • Test example 3 The plastic pot was filled with soil, cucumber (variety: Sagamihanjiro) was sown and grown in a greenhouse for 12 days.
  • Each of the compounds (17), (18) and (19) 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 adheres well to the cucumber leaf surface. The foliage was sprayed.
  • test example 4 A plastic pot was stuffed with soil, seeded with green beans (variety; Nagahama peas) and grown in a greenhouse for 8 days.
  • Each of the compounds (16), (17), (18), (89), (95), (96) and (101) of the present invention was made into a flowable formulation according to Formulation Example 6, then diluted with water to give The concentration was set to 500 ppm, and the foliage was sprayed so as to adhere well to the kidney leaf surface. After spraying, the plants were air-dried, and a mycelia-containing PDA medium of Sclerotinia sclerotiorum was placed on the kidney leaf surface. After inoculation, the lesion area was investigated after 23 days at 23 ° C. and high humidity.
  • the lesion area in the plant treated with the compounds (16), (17), (18), (89), (95), (96) and (101) of the present invention is the lesion spot in the untreated plant. It was 30% or less of the area.
  • Test Example 5 Cucumber downy mildew treatment effect test (Pseudoperonospora cubensis) The plastic pot was filled with soil, cucumber (variety: Sagamihanjiro) was sown and grown in a greenhouse for 12 days. The pot was spray-inoculated with an aqueous suspension of cucumber downy mildew zoosporangium, placed at 23 ° C.
  • the plants were air-dried and placed in a greenhouse at 23 ° C. for 5 days, and then the lesion area was examined.
  • the present compounds (10), (12), (13), (14), (16), (27), (33), (36), (37), (40), (41), (43), (49), (52), (56), (57), (58), (59), (61), (62), (63), (64), (65), (66 ), (69), (72), (75), (76), (77), (78), (81), (82), (84), (86), (89), (90),
  • the lesion area in the plant which processed (91), (92), (99), (100), (101), (102) and (110) is 30% or less of the lesion area in an untreated plant.
  • Test Example 6 The plastic pot was filled with soil, tomato (variety: patio) was sown and grown in a greenhouse for 20 days.
  • Compounds of the present invention (1), (2), (3), (4), (5), (6), (7), (8), (9), (10), (11), (12) , (13), (14), (15), (16), (17), (26), (27), (28), (30), (31), (33), (35), ( 36), (37), (38), (39), (40), (41), (43), (45), (49), (50), (52), (56), (57) , (58), (59), (61), (62), (63), (64), (65), (69), (71), (72), (73), (75), ( 76), (77), (78), (80), (81), (82), (84), (85), (86), (88), (89), (90), (91) , (92), (93), (94), (95), (96), ( 7), (98), (99), (100), (101), (
  • 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.
  • Test Example 7 The plastic pot was filled with soil, tomato (variety: patio) was sown and grown in a greenhouse for 20 days.
  • Each of the compounds (18), (20), (21), (22) and (23) of the present invention was made into a flowable formulation according to Formulation Example 6, then diluted with water to a predetermined concentration (200 ppm), and the tomato The foliage was sprayed so as to adhere well to the leaf surface of the seedling. 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.
  • Test Example 8 Tomato (variety: patio) was sown on a plastic sponge piece and hydroponically cultivated in a plastic cup for about 20 days.
  • Compound (1), (2), (4), (5), (6), (7), (8), (9), (10), (11), (12), (13) , (14), (15), (16), (17), (26), (33), (36), (40), (41), (43), (49), (52), ( 53), (62), (63), (65), (72), (75), (76), (77), (78), (81), (82), (84), (85) , (86), (87), (88), (89), (90), (91), (93), (94), (95), (96), (97), (98), ( 99), (100), (101), (102), (106) and (110) are each made into a flowable formulation according to Formulation Example 6, and then 1 mg of the above tomato hydroponics per plant in terms of weight In a seedling cup Off to.
  • 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.
  • Test Example 9 Tomato (variety: patio) was sown on a plastic sponge piece and hydroponically cultivated in a plastic cup for about 20 days.
  • Each of the compounds (18), (20), (21), (22) and (23) of the present invention was made into a flowable formulation according to Formulation Example 6, and then 0.4 mg per plant in terms of weight was added to the tomato water. It put into the cup of the cultivation seedling. 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 (18), (20), (21), (22) and (23) 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.

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Abstract

L'invention porte sur un composé amide représenté par la formule (1) [dans laquelle R1 représente un atome d'hydrogène, un atome d'halogène, un groupe cyano, un groupe nitro ou similaire ; p représente un entier de 0 à 5 ; et R2 représente un atome d'halogène, un groupe cyano, un groupe nitro ou similaire] ou un sel de celui-ci, qui a un excellent effet de lutte contre les maladies des plantes.
PCT/JP2010/058856 2009-05-20 2010-05-19 Composé amide et son utilisation pour la lutte contre les maladies des plantes WO2010134628A1 (fr)

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Cited By (1)

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WO2023176458A1 (fr) * 2022-03-18 2023-09-21 石原産業株式会社 Composition désinfectante contenant un composé hydrazide d'acide thiazole carboxylique

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