WO2010134636A1 - 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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WO2010134636A1
WO2010134636A1 PCT/JP2010/058864 JP2010058864W WO2010134636A1 WO 2010134636 A1 WO2010134636 A1 WO 2010134636A1 JP 2010058864 W JP2010058864 W JP 2010058864W WO 2010134636 A1 WO2010134636 A1 WO 2010134636A1
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group
halogen
optionally substituted
compound
mixture
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PCT/JP2010/058864
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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 WO2010134636A1 publication Critical patent/WO2010134636A1/fr

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    • 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
    • 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
    • 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

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 2 may be the same as or different from each other, and may be substituted with one or more groups selected from group C, which may be substituted with one or more groups selected from group C;
  • Group C is a C3-C10 cycloalkyl group which may be substituted with one or more groups selected from Group D, a halogen, a cyano group, a C1-C4 alkoxy group which may be substituted with halogen, or a halogen
  • An optionally substituted C1-C4 alkylthio group, an optionally substituted C1-C4 alkylsulfinyl group, an optionally substituted C1-C4 alkylsulfonyl group, and an optionally substituted 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, cyan
  • an salt thereof (hereinafter referred to as the present compound).
  • [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.
  • a plant disease control agent comprising the amide compound or salt thereof according to any one of [1] to [7] 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 [7] to a plant or a soil in which the plant grows.
  • 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 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-t
  • 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, 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-fluoroprop
  • 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 2 Is a C1-C5 chain hydrocarbon group optionally substituted with one or more groups selected from group C, C3-C10 cycloalkyl group optionally substituted with one or more groups selected from group D, Represents a phenyl group, a halogen, a cyano group or a nitro group which may be substituted with one or more groups selected from E, or two R 2 When the carbons on the benzene ring to which are bonded are adjacent, the two R 2 Are together, a C2-C5 polymethylene group optionally substituted with one or more groups selected from group E, and propene-1,3-diyl optionally substituted with one or more groups selected from group E An amide compound which is a 1,3-butadiene-1,4-diyl group or a methylenedioxy group optionally substituted by one or more groups selected from the group, group E; In formula (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.
  • a dehydration condensing agent [In the formula, 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.
  • R 2 And p represent the same meaning as described above.
  • the reaction is usually performed in the presence of a solvent.
  • 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.
  • 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.
  • the compound of the present invention can be produced, for example, from compound (5) according to the following scheme. [In the formula, R 2 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.
  • a solvent 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 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.
  • 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 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, granule, dry flowable liquid, emulsion, aqueous liquid, oil, smoke, aerosol, microcapsule 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%.
  • 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), and aromatics.
  • Hydrocarbons eg, benzene, toluene, xylene, ethylbenzene, methylnaphthalene
  • aliphatic hydrocarbons eg, hexane, cyclohexanone, kerosene
  • esters eg, ethyl acetate, butyl acetate
  • nitriles eg, Acetonitrile, isobutyronitrile
  • ethers eg geo Sun, diisopropyl ether
  • acid amides e.g., dimethylformamide, dimethylacetamide
  • halogenated hydrocarbons e.g., dichloroethane, trichlorethylene, and carbon tetrachloride
  • 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, 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.
  • fixing agents eg starch, arabic gum, cellulose derivatives, Alginic acid
  • lignin derivatives bentonite
  • saccharides eg, synthetic water-soluble polymers (
  • 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.
  • 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, 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,
  • 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.
  • 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 mixture was stirred for 5 minutes under ice cooling, and then stirred for 4.5 hours at room temperature.
  • the reaction mixture was left overnight at room temperature, and the reaction mixture was poured into 10 mL of saturated aqueous sodium bicarbonate.
  • the mixture was extracted with ethyl acetate, washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography.
  • the mixture was stirred for 5 minutes under ice-cooling and then stirred at room temperature for 1.5 hours.
  • the reaction mixture was left overnight at room temperature, and the reaction mixture was poured into 10 mL of saturated aqueous sodium bicarbonate.
  • the mixture was extracted with ethyl acetate, washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure.
  • the resulting residue was washed with chloroform, and 2-amino-4-methyl-N- ( ⁇ -naphthylmethyl) -thiazole-5-carboxylic acid amide (hereinafter referred to as the present compound (6)) was reduced to 0. 39 g was obtained.
  • the mixture was stirred under ice-cooling for 5 minutes and then stirred at room temperature for 11.5 hours.
  • the reaction mixture was poured into 10 mL of saturated aqueous sodium bicarbonate and extracted with ethyl acetate. The extract was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography.
  • the mixture was stirred for 5 minutes under ice-cooling and then stirred at room temperature for 1.5 hours.
  • the reaction mixture was allowed to stand at room temperature overnight, then poured into 10 mL of saturated aqueous sodium hydrogen carbonate, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography.
  • the mixture was stirred for 5 minutes under ice-cooling and then stirred at room temperature for 1.5 hours.
  • the reaction mixture was allowed to stand at room temperature overnight, then poured into 10 mL of saturated aqueous sodium hydrogen carbonate, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography.
  • the mixture was stirred under ice-cooling for 5 minutes and then stirred at room temperature for 3.5 hours.
  • the reaction mixture was allowed to stand at room temperature overnight, then poured into 10 mL of saturated aqueous sodium hydrogen carbonate, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography.
  • the obtained residue was subjected to silica gel column chromatography.
  • the obtained 2-amino-N- (4-fluoro-2-trifluoromethyl-benzyl) -4-methyl-thiazole-5-carboxylic acid amide was washed with a mixed solution of ethyl acetate and hexane to give 2-amino- 0.52 g of N- (4-fluoro-2-trifluoromethyl-benzyl) -4-methyl-thiazole-5-carboxylic acid amide (hereinafter referred to as the present compound (15)) was obtained.
  • the mixture was stirred for 5 minutes under ice-cooling and then stirred at room temperature for 0.5 hour.
  • the reaction mixture was allowed to stand at room temperature for 3 days, poured into 10 mL of saturated aqueous sodium hydrogen carbonate, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was washed with ethyl acetate and chloroform in this order, and 2-amino-4-methyl-N- (2-methyl-3-nitro-benzyl) -thiazole-5-carboxylic acid amide (hereinafter referred to as the present compound ( 18) was obtained 0.47 g.
  • the mixture was stirred for 5 minutes under ice-cooling and then stirred at room temperature for 2 hours.
  • the reaction mixture was allowed to stand at room temperature overnight, then poured into 10 mL of saturated aqueous sodium hydrogen carbonate, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography.
  • Production Example 24 Mix 0.32 g of 2-amino-4-methylthiazole-5-carboxylic acid, 3 mL of DMF, 0.49 g of triethylamine, 1.06 g of BOP reagent, and 0.45 g of 2-chloro-5-nitrobenzylamine hydrochloride. 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 25 A mixture of 0.32 g of 2-amino-4-methylthiazole-5-carboxylic acid, 3 mL of DMF, 0.49 g of triethylamine, 1.06 g of BOP reagent, and 0.42 g of 4-fluoro-2-nitrobenzylamine hydrochloride, 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 27 A mixture of 0.32 g of 2-amino-4-methylthiazole-5-carboxylic acid, 3 mL of DMF, 0.49 g of triethylamine, 1.06 g of BOP reagent, and 0.43 g of 2-chloro-4,5-difluorobenzylamine hydrochloride 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.
  • Production Example 28 A mixture of 0.32 g of 2-amino-4-methylthiazole-5-carboxylic acid, 3 mL of DMF, 0.71 g of triethylamine, 1.06 g of BOP reagent, and 0.52 g of 2-bromo-4,5-difluorobenzylamine hydrochloride 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.
  • Production Example 29 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 0.31 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 30 Mix 0.32 g of 2-amino-4-methylthiazole-5-carboxylic acid, 3 mL of DMF, 0.49 g of triethylamine, 1.06 g of BOP reagent, and 0.52 g of 2-bromo-3,5-difluorobenzylamine hydrochloride. 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.
  • Production Example 31 Mix 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 3,4,5-trifluoro-2-methylbenzylamine And the mixture was stirred at room temperature for 7 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 33 Mix 0.32 g of 2-amino-4-methylthiazole-5-carboxylic acid, 3 mL of DMF, 0.49 g of triethylamine, 1.06 g of BOP reagent, and 0.43 g of 2,3,4,5-tetrafluorobenzylamine hydrochloride And 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.
  • Production Example 34 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 0.31 g of 4,5-difluoro-2-methylbenzylamine, 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.
  • reaction mixture was left overnight at room temperature, and 15 mL of aqueous ammonia (28%) was added. After stirring at room temperature for 3 hours, 46.4 mL of 4N aqueous sodium hydroxide solution was added. After stirring at room temperature for 1 hour, 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.
  • reaction mixture was left overnight at room temperature, and 30 mL of aqueous ammonia (28%) was added. After stirring at room temperature for 3 hours, 94 mL of 4N aqueous sodium hydroxide solution was added. After stirring at room temperature for 1 hour, 177 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 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. After extraction with t-butyl methyl ether, water and saturated brine were washed 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. Thereafter, the mixture was allowed to stand at room temperature for 3 days, 28 mL of aqueous ammonia (28%) was added to the mixture, and the mixture was 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.
  • Formulation Example 1 Each wettable powder is obtained by thoroughly pulverizing and mixing 50 parts of any one of the compounds (1) to (36) 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 (36) 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 is obtained by thoroughly pulverizing and mixing 2 parts of any one of the compounds (1) to (36) 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 (36) 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 (36) 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 (36) 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 (36) of the present invention, 38.5 parts of NN kaolin clay (manufactured by Takehara Chemical Industries), 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 The plastic pot was filled with soil, tomato (variety: patio) was sown and grown in a greenhouse for 20 days.
  • Compound (5), (8), (9), (12), (13), (14), (15), (16), (17), (18), (19), (20) , (21), (24), (28), (30), (32), (35) and (36) are each made into a flowable formulation according to Formulation Example 6, and then diluted with water to a predetermined concentration ( 500 ppm) and sprayed with foliage so that the leaves would adhere well to the leaves of the tomato seedlings. After air-drying the diluted solution on the leaf surface to dryness, an aqueous suspension of Phytophthora infestans spores was spray-inoculated.
  • 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 2 The plastic pot was filled with soil, tomato (variety: patio) was sown and grown in a greenhouse for 20 days.
  • 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 (200 ppm), and sprayed with foliage so as to adhere well to the leaf surface of the tomato 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. for 4 days. The lesion area in the plant which processed this invention compound (2) was 30% or less of the lesion area in an untreated plant.
  • Test example 3 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) and (3) of the present invention is made into a flowable formulation according to Formulation Example 6, and then diluted with water to a predetermined concentration (50 ppm) and sprayed with foliage to adhere well to the leaves of the tomato seedlings. did.
  • 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) and (3) was 30% or less of the lesion area in an untreated plant.
  • Test example 4 Tomato (variety: patio) was sown on a plastic sponge piece and hydroponically cultivated in a plastic cup for about 20 days.
  • Compound (3), (5), (8), (9), (12), (13), (14), (15), (16), (17), (18), (20) , (24), (26), (28), (29), (30), (31), (32) and (34) are made into a flowable preparation according to Preparation Example 6 and then converted into one plant by weight. 1 mg per unit was put into the cup of the tomato hydroponic seedling.
  • each of the compounds (11) and (36) of the present invention was made into a flowable formulation according to Formulation Example 6, and then diluted with water to a predetermined concentration (500 ppm), so that the foliage was sufficiently adhered to the rice leaf surface. Scattered. After spraying, the plants were air-dried and placed in contact with rice seedlings (variety: Nipponbare) affected by blast fungus (Magnaporthe oryzae) at 24 ° C in the daytime and 20 ° C in the nighttime at high humidity. did. As a result, the lesion area in the plant treated with the present compounds (11) and (36) was 30% or less of the lesion area in the untreated plant.
  • Test Example 8 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 (29) 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 adhered sufficiently to the leaf surface of the wheat.
  • Test Example 9 A plastic pot was filled with soil, seeded with wheat (variety: Apogee), and grown in a greenhouse for 10 days. Each of the compounds (5), (9), (25), (29), (32), and (34) of the present invention was made into a flowable formulation according to Formulation Example 6, and then diluted with water to give a predetermined concentration (500 ppm) Then, the leaves were sprayed so as to adhere well to the leaf surface of the wheat.
  • 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 (5), (14), (15), (16), (18), (20), (25), (29), (32), (34), and (35) of the present invention is formulated.
  • Test Example 11 The plastic pot was filled with soil, cucumber (variety: Sagamihanjiro) was sown and grown in a greenhouse for 12 days.
  • the compound (22) 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 as to adhere well to the cucumber leaf surface.
  • Test Example 12 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 (5), (27), (28), (31), (33), and (34) of the present invention was made into a flowable formulation according to Formulation Example 6 and then diluted with water to give a predetermined concentration (500 ppm) Then, the foliage was sprayed so as to adhere sufficiently to the surface of the kidney beans. After spraying, the plants were air-dried, and a mycelia-containing PDA medium of sclerotia sclerotium was placed on the kidney leaf surface. After inoculation, the lesion area was investigated after 23 days at 23 ° C. and high humidity. As a result, the lesion area in the plant treated with the compounds (5), (27), (28), (31), (33), (34) of the present invention was 30% of the lesion area in the untreated plant. It was the following.
  • 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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  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
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Abstract

L'invention porte sur un composé amide représenté par la formule (1) [dans laquelle p représente un entier de 2 à 5, et R2 tel que défini dans la description et 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/JP2010/058864 2009-05-20 2010-05-19 Composé amide et son utilisation pour la lutte contre les maladies des plantes WO2010134636A1 (fr)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1211889A (en) * 1966-12-07 1970-11-11 Uniroyal Inc The use of carboxamidothiazoles as agricultural chemicals
JPH04128275A (ja) * 1990-09-19 1992-04-28 Mitsubishi Kasei Corp Ｎ―ベンジルアミド類およびこれを有効成分とする殺虫、殺ダニ剤
JPH0789946A (ja) * 1993-08-16 1995-04-04 Lucky Co Ltd 新規２−アミノチアゾルカルボキサミド誘導体、その製造方法及び植物病原菌用抗菌剤
JP2001342183A (ja) * 2000-06-01 2001-12-11 Ube Ind Ltd ４−（１−フルオロエチル）チアゾール−５−カルボン酸アミド誘導体及び農園芸用の有害生物防除剤
WO2007087906A1 (fr) * 2006-02-01 2007-08-09 Bayer Cropscience Sa Dérivés fongicides de n-cycloalkyl-benzylamide
WO2010012794A1 (fr) * 2008-08-01 2010-02-04 Bayer Cropscience Sa Dérivés de n-cycloalkyl-n-biphénylméthyl-carboxamide fongicides

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1211889A (en) * 1966-12-07 1970-11-11 Uniroyal Inc The use of carboxamidothiazoles as agricultural chemicals
JPH04128275A (ja) * 1990-09-19 1992-04-28 Mitsubishi Kasei Corp Ｎ―ベンジルアミド類およびこれを有効成分とする殺虫、殺ダニ剤
JPH0789946A (ja) * 1993-08-16 1995-04-04 Lucky Co Ltd 新規２−アミノチアゾルカルボキサミド誘導体、その製造方法及び植物病原菌用抗菌剤
JP2001342183A (ja) * 2000-06-01 2001-12-11 Ube Ind Ltd ４−（１−フルオロエチル）チアゾール−５−カルボン酸アミド誘導体及び農園芸用の有害生物防除剤
WO2007087906A1 (fr) * 2006-02-01 2007-08-09 Bayer Cropscience Sa Dérivés fongicides de n-cycloalkyl-benzylamide
WO2010012794A1 (fr) * 2008-08-01 2010-02-04 Bayer Cropscience Sa Dérivés de n-cycloalkyl-n-biphénylméthyl-carboxamide fongicides

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