JP2011001294A - Amide compound and application thereof for controlling plant disease - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a compound exhibiting excellent controlling efficacy on a plant disease.SOLUTION: The amide compound represented by formula (I) (wherein Ris a methyl group and Ris a fluorine atom or a trifluoromethyl group; or Ris an ethyl group and Ris a fluorine atom or a trifluoromethoxy group) exhibits excellent controlling efficacy on a plant disease.

Description

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

  Drugs for controlling plant diseases have been developed, and many compounds having a plant disease control effect have been found, but the effect may not be sufficient, and a search for new compound groups has been conducted eagerly. Yes.

  An object of the present invention is to provide a compound having an excellent control effect against plant diseases.

〔式中、
Ｒ¹はメチル基を表し、Ｒ²はフッ素原子又はトリフルオロメチル基を表すか、或いは、Ｒ¹はエチル基を表し、Ｒ²はフッ素原子又はトリフルオロメトキシ基を表す。〕
で示されるアミド化合物（以下、本発明化合物と記す。）。
〔２〕 〔１〕記載のアミド化合物を有効成分として含有する植物病害防除剤（以下、本発明防除剤と記す。）。
〔３〕 〔１〕記載のアミド化合物の有効量を植物又は土壌に処理する工程を有してなる植物病害の防除方法（以下、本発明防除方法と記す。）。
〔４〕 植物又は土壌に処理することにより、植物病害を防除するための〔１〕記載のアミド化合物の使用。 As a result of studying to find a compound having an excellent control effect against plant diseases, the present inventor has found that the amide compound represented by the following formula (I) has an excellent control effect against plant diseases, The present invention has been reached.
That is, the present invention is as follows [1] to [4].
[1] Formula (I)

[Where,
R ¹ represents a methyl group, R ² represents a fluorine atom or a trifluoromethyl group, or R ¹ represents an ethyl group, and R ² represents a fluorine atom or a trifluoromethoxy group. ]
(Hereinafter referred to as the present compound).
[2] A plant disease control agent containing the amide compound according to [1] as an active ingredient (hereinafter referred to as the present invention control agent).
[3] A plant disease control method comprising a step of treating an effective amount of the amide compound according to [1] to a plant or soil (hereinafter referred to as the present invention control method).
[4] Use of the amide compound according to [1] for controlling plant diseases by treating the plant or soil.

  According to the present invention, plant diseases can be controlled.

The manufacturing method of this invention compound is demonstrated.
The compound of the present invention can be produced, for example, by the following (Production Method 1) or (Production Method 2).

〔式中、Ｒ¹及びＲ²は前記と同じ意味を表す。〕
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばテトラヒドロフラン（以下、ＴＨＦと記す場合がある。）、エチレングリコールジメチルエーテル、ｔｅｒｔ−ブチルメチルエーテル（以下、ＭＴＢＥと記す場合がある。）等のエーテル類、ヘキサン、へプタン、オクタン等の脂肪族炭化水素類、トルエン、キシレン等の芳香族炭化水素類、クロロベンゼン等のハロゲン化炭化水素類、酢酸ブチル、酢酸エチル等のエステル類、アセトニトリル等のニトリル類、Ｎ，Ｎ−ジメチルホルムアミド（以下、ＤＭＦと記す場合がある。）等の酸アミド類、ジメチルスルホキシド（以下、ＤＭＳＯと記す場合がある。）等のスルホキシド類、ピリジン等の含窒素芳香族化合物類等及びこれらの混合物が挙げられる。
反応に用いられる脱水縮合剤としては、１−エチル−３−（３−ジメチルアミノプロピル）カルボジイミド塩酸塩（以下、ＷＳＣと記す。）及び１，３−ジシクロヘキシルカルボジイミド等のカルボジイミド類、（ベンゾトリアゾール−１−イルオキシ）トリス（ジメチルアミノ）ホスホニウムヘキサフルオロホスフェート（以下、ＢＯＰ試薬と記す場合がある。）等が挙げられる。
化合物（ＩＩ）１モルに対して、化合物（ＩＩＩ）が通常０．５〜３モルの割合、脱水縮合剤が通常１〜５モルの割合で用いられる。
該反応の反応温度は、通常−２０℃〜１４０℃の範囲であり、反応時間は通常１〜２４時間の範囲である。
反応終了後は、反応混合物に水を加えた後、固体が析出した場合は、濾過することにより本発明化合物を単離することができ、また、固体が析出しない場合は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、本発明化合物を単離することができる。単離された本発明化合物は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Production method 1)
The compound of the present invention is produced by reacting compound (II) with compound (III) or a salt thereof (for example, hydrochloride and hydrobromide) in the presence of a dehydration condensing agent. Can do.

[Wherein, R ¹ and R ² represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as tetrahydrofuran (hereinafter sometimes referred to as THF), ethylene glycol dimethyl ether, tert-butyl methyl ether (hereinafter sometimes referred to as MTBE), hexane, and the like. Aliphatic hydrocarbons such as pentane 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 dimethyl sulfoxide (hereinafter sometimes referred to as DMSO), nitrogen-containing aromatic compounds such as pyridine, and the like Of the mixture.
Examples of the dehydrating condensing agent used in the reaction include 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride (hereinafter referred to as WSC) and carbodiimides such as 1,3-dicyclohexylcarbodiimide, (benzotriazole- 1-yloxy) tris (dimethylamino) phosphonium hexafluorophosphate (hereinafter sometimes referred to as BOP reagent) and the like.
The compound (III) is usually used in a proportion of 0.5 to 3 mol and the dehydrating condensing agent is usually used in a proportion of 1 to 5 mol with respect to 1 mol of the compound (II).
The reaction temperature of the reaction is usually in the range of -20 ° C to 140 ° C, and the reaction time is usually in the range of 1 to 24 hours.
After completion of the reaction, after adding water to the reaction mixture, if a solid precipitates, the compound of the present invention can be isolated by filtration. If the solid does not precipitate, the reaction mixture is added to an organic solvent. The compound of the present invention can be isolated by performing post-treatment operations such as extraction with, 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.

〔式中、Ｒ¹及びＲ²は前記と同じ意味を表す。〕
該反応は、通常溶媒の存在下で行われる。
反応に用いられる溶媒としては、例えばＴＨＦ、エチレングリコールジメチルエーテル、ＭＴＢＥ等のエーテル類、ヘキサン、へプタン、オクタン等の脂肪族炭化水素類、トルエン、キシレン等の芳香族炭化水素類、クロロベンゼン等のハロゲン化炭化水素類、酢酸ブチル、酢酸エチル等のエステル類、アセトニトリル等のニトリル類及びこれらの混合物が挙げられる。
反応に用いられる塩基としては、炭酸ナトリウム、炭酸カリウム等のアルカリ金属炭酸塩類、トリエチルアミン、ジイソプロピルエチルアミン等の第３級アミン類及びピリジン、４−ジメチルアミノピリジン等の含窒素芳香族化合物類等が挙げられる。
化合物（ＩＶ）１モルに対して、化合物（ＩＩＩ）が通常０．５〜３モルの割合、塩基が通常１〜５モルの割合で用いられる。
該反応の反応温度は通常−２０〜１００℃の範囲であり、反応時間は通常０．１〜２４時間の範囲である。
反応終了後は、反応混合物に水を加えた後、固体が析出した場合は、濾過することにより本発明化合物を単離することができ、また、固体が析出しない場合は、反応混合物を有機溶媒で抽出し、有機層を乾燥、濃縮する等の後処理操作を行うことにより、本発明化合物を単離することができる。単離された本発明化合物は、クロマトグラフィー、再結晶等によりさらに精製することもできる。 (Production method 2)
The compound of the present invention comprises compound (IV) or a salt thereof (for example, hydrochloride) and compound (III) or a salt thereof (for example, hydrochloride and hydrobromide) as a base. It can also manufacture by making it react in presence of.

[Wherein, R ¹ and R ² represent the same meaning as described above. ]
The reaction is usually performed in the presence of a solvent.
Examples of the solvent used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, and MTBE, aliphatic hydrocarbons such as hexane, heptane, and octane, aromatic hydrocarbons such as toluene and xylene, and halogens such as chlorobenzene. Hydrocarbons, esters such as butyl acetate and ethyl acetate, nitriles such as acetonitrile, and mixtures thereof.
Examples of the base used in the reaction include alkali metal carbonates such as sodium carbonate and potassium carbonate, tertiary amines such as triethylamine and diisopropylethylamine, and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine. It is done.
The compound (III) is usually used in a proportion of 0.5 to 3 mol and the base is usually used in a proportion of 1 to 5 mol with respect to 1 mol of the compound (IV).
The reaction temperature of the reaction is usually in the range of -20 to 100 ° C, and the reaction time is usually in the range of 0.1 to 24 hours.
After completion of the reaction, after adding water to the reaction mixture, if a solid precipitates, the compound of the present invention can be isolated by filtration. If the solid does not precipitate, the reaction mixture is added to an organic solvent. The compound of the present invention can be isolated by performing post-treatment operations such as extraction with, 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 control agent of the present invention is prepared by mixing the compound of the present invention with a solid carrier, liquid carrier, gas carrier, surfactant, etc., and if necessary, adding an auxiliary for formulation such as a fixing agent, a dispersant, a stabilizer, It is formulated into a powder, wettable powder, flowable powder, granule, dry flowable powder, emulsion, aqueous liquid, oil, smoke, aerosol, microcapsule and the like. These preparations usually contain 0.1 to 99%, preferably 0.2 to 90% by weight of the compound of the present invention.

  Examples of the solid carrier include clays (for example, kaolin, diatomaceous earth, synthetic hydrous silicon oxide, fusami clay, bentonite, acidic clay), talc, and other inorganic minerals (for example, sericite, quartz powder, sulfur powder, activated carbon, Examples of the liquid carrier include water, alcohols (for example, methanol, ethanol), ketones (for example, acetone, methyl ethyl ketone), aromatic carbonization, and the like. Hydrogens (eg, benzene, toluene, xylene, ethylbenzene, methylnaphthalene), aliphatic hydrocarbons (eg, n-hexane, cyclohexanone, kerosene), esters (eg, ethyl acetate, butyl acetate), nitriles (eg, , Acetonitrile, isobutylnitrile), ethers (eg , Dioxane, diisopropyl ether), acid amides (e.g., dimethylformamide, dimethylacetamide), halogenated hydrocarbons (e.g., dichloroethane, trichlorethylene, and carbon tetrachloride), and the like.

  Examples of the surfactant include alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and polyoxyethylene compounds thereof, polyoxyethylene glycol ethers, polyhydric alcohol esters, sugar alcohol derivatives. Etc.

  Other formulation adjuvants include, for example, fixing agents and dispersants, specifically casein, gelatin, polysaccharides (eg starch, arabic gum, cellulose derivatives, alginic acid), lignin derivatives, bentonite, saccharides, synthetic water-soluble high Molecules (for example, polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acids), PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (2-tert-butyl-4) -Mixtures of methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oils, mineral oils, fatty acids or esters thereof.

  The method of applying the control agent of the present invention is not particularly limited as long as the control agent of the present invention can be applied substantially, but for example, treatment to plant bodies such as foliage spraying, plant such as soil treatment, etc. And the like, and the treatment of seeds such as seed disinfection.

〔式中、Ｘ¹は水素原子、またはハロゲン原子を表し、Ｘ²はメチル基、ジフルオロメチル基、又はトリフルオロメチル基を表し、Ｑは下記のいずれかの基

を表す。〕
で示されるピラゾールカルボキサミド化合物；

式（１２）

〔式中、Ｘ³はメチル基、ジフルオロメチル基、またはエチル基を表し、Ｘ⁴はメトキシ基、またはメチルアミノ基を表し、Ｘ⁵はフェニル基、２−メチルフェニル基、または２，５−ジメチルフェニル基を表す。〕
で示されるα−アルコキシフェニル酢酸化合物；
式（１３）

〔式中、Ｘ⁶はメトキシ基、エトキシ基、プロポキシ基、２−プロペニルオキシ基、２−プロピニルオキシ基、３−ブテニルオキシ基、３−ブチニルオキシ基、メチルチオ基、エチルチオ基、または２−プロペニルチオ基を表し、Ｘ⁷は１−メチルエチル基、または１−メチルプロピル基を表し、Ｘ⁸は２−メチルフェニル基、または２，６−ジクロロフェニル基を表す。〕
で示されるピラゾリノン化合物、
等があげられる。 In addition, the present control agent may be used simultaneously with or without mixing with other fungicides, insecticides, acaricides, nematicides, herbicides, plant growth regulators, fertilizers or soil conditioners. You can also.
Such other fungicides include, for example,
(1) Azole fungicides propiconazole, prothioconazole, triadimenol, prochloraz, penconazole, zebolazole, tebuconazole, tebuconazole diconazole, bromuconazole, epoxyconazole, difenoconazole, cyproconazole, metconazole, metconazole, metconazole, metconazole, metconazole, metconazole, metconazole, metconazole, metconazole, metconazole, metconazole, metconazole. Traconazole, microbutanil, fenbuconazole, hexaconazole, fluquinconazole, triticonazole, triticonazole, triticonazole, triticonazole, triticonazole, triticonazole , Flutriafol, simeconazole, ipconazole, etc .;
(2) Amine-based fungicides fenpropimorph, tridemorph, fenpropidin, spiroxamine, etc .;
(3) benzimidazole fungicides carbendazim, benomyl, thiabendazole, thiophanate-methyl and the like;
(4) Dicarboximide fungicides procymidone, iprodione, vinclozolin and the like;
(5) Anilinopyrimidine fungicides cyprodinil, pyrimethanil, mepanipyrim and the like;
(6) Phenylpyrrole fungicide fenpiclonil, fludioxonil, etc .;
(7) The strobilurin fungicide cresoxim-methyl, azoxystrobin, trifloxystrobin, floxastrobin, picoxystrobin (picoxystrobin) pyraclostrobin, dimoxystrobin, pyribencarb, methinostrobin, oryzatrobin, enestrobin, etc .;
(8) Phenylamide fungicides metalaxyl, metalaxyl M or mephenoxam, benalaxyl, benalaxyl M or beilaxyl-ra
(9) Carboxylic acid amide fungicide dimethomorph, iprovalicalb, benchavaricarb-isopropyl, mandipropamide, varifenal
(10) Carboxamide fungicides carboxin, mepronil, flutolanil, thifluzamide, furamethpyr, boscalid, penthipyrdo, pentiopyrad bifafen),
(11) Other fungicides dietofencarb; thiuram; fluazinam; mancozeb; chlorothalonil; captan; diclofluuride; folpette; quinoxyphene; Flupicolide; fluorpicolide; focetyl; simoxanyl; pencyclon; tolcrofosmethyl; carpropamide; diclocimet; phenoxanyl; tricyclazole; pyroxilone; probenazole; Isoproti Oran; Oxolinic acid; Oxytetracycline; Streptomycin; Basic copper chloride; Cupric hydroxide; Basic copper sulfate; Organic copper;

Formula (11)

[Wherein, X ¹ represents a hydrogen atom or a halogen atom, X ² represents a methyl group, a difluoromethyl group, or a trifluoromethyl group, and Q represents any of the following groups:

Represents. ]
A pyrazole carboxamide compound represented by:

Formula (12)

[Wherein, X ³ represents a methyl group, a difluoromethyl group or an ethyl group, X ⁴ represents a methoxy group or a methylamino group, X ⁵ represents a phenyl group, a 2-methylphenyl group, or 2,5- Represents a dimethylphenyl group. ]
An α-alkoxyphenylacetic acid compound represented by:
Formula (13)

[Wherein, X ⁶ is a methoxy group, an ethoxy group, a propoxy group, a 2-propenyloxy group, a 2-propynyloxy group, a 3-butenyloxy group, a 3-butynyloxy group, a methylthio group, an ethylthio group, or a 2-propenylthio group. X ⁷ represents a 1-methylethyl group or a 1-methylpropyl group, and X ⁸ represents a 2-methylphenyl group or a 2,6-dichlorophenyl group. ]
A pyrazolinone compound represented by:
Etc.

Examples of such other insecticides include: (1) Organophosphorus compounds: acephate, aluminum phosphide, butathiofos, cadusafos, chlorethoxyfos, chlorfenvinphos (Ch1orfenvinphos), chlorpyrifos (chlorpyrifos), chlorpyrifos-methyl, cyanophos (CYAP), diazinon (diazinon), DCIP (dichlorodiisopropyl ether), dichlorfenthion (ECP), dichlorvos (DDVP), dimethophos (Dimethoate), dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, etrimfos, fenthion (MPP), fenitrothion (MEP), phos Azate (fosthiazate), formothion, hydrogen phosphide, isofenphos, isoxathion, malathion, mesulfenfos, methidathion (DMTP), monocrotophos (monocrotophos) , Naled (BRP), oxydeprofos (ESP), parathion, parathion, phosalone, phosmet (PMP), pyrimiphos-methy1, pyridafenthion, quinalphos , Phenthoate (PAP), profenofos, propaphos, prothiofos, pyraclorfos, salithion, sulprofos, tebupirimfos, temephos os), tetrach1orvinphos, terbufos, thiometon, trichlorphon (DEP), bamidomion, phorate, cadusafos, etc .;
(2) Carbamate compounds Alananicarb, bendiocarb, benfuracarb, BPMC, carbaryl, carbfuran, carbosulfan, cloethocarb, ethiofencarb ), Fenobucarb, fenothiocarb, fenoxycarb, furathiocarb, isoprocarb (MIPC), metolcarb, metomyl, methiocarb, NAC, oxamyl (amyl) ), Pirimicarb, propoxur (PHC), XMC, thiodicarb, xylylcarb, aldicarb, etc .;
(3) Synthetic pyrethroid compounds Acrinathrin, allethrin, benfluthrin, beta-cyfluthrin, bifenthrin, cycloprothrin, cyfluthrin, cyhalothrin (cyfluthrin) cyhalothrin), cypermethrin, deltamethrin, esfenvalerate, ethofenprox, fenpropathrin, fenvalerate, flucythrinate, flufenthrinate Prox (flufenoprox), flumethrin, fluvalinate, halfenprox (halfenprox), imiprothrin, permethrin, praretrin (pi) Threin (pyrethrins), resmethrin, sigma-cypermethrin, silafluofen, tefluthrin, tralomethrin, transfluthrin, tetramethrin, othrin Cyphenothrin, alpha-cypermethrin, zeta-cypermethrin, lambda-cyhalothrin, furamethrin, tau-fluvalinate, 2 , 3,5,6-tetrafluoro-4- (methoxymethyl) benzyl (EZ)-(1RS, 3RS; 1RS, 3SR) -2,2-dimethyl-3-prop-1-enylcyclopropanecarboxylate, 2 , 3,5,6-tetrafluoro-4- Tylbenzyl (EZ)-(1RS, 3RS; 1RS, 3SR) -2,2-dimethyl-3-prop-1-enylcyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4- (methoxymethyl) Benzyl (1RS, 3RS; 1RS, 3SR) -2,2-dimethyl-3- (2-methyl-1-propenyl) cyclopropanecarboxylate and the like;
(4) Nereistoxin compounds Cartap, bensu1tap, thiocyclam, monosultap, bisultap, etc .;
(5) Neonicotinoid compounds imidacloprid (imidac1oprid), nitenpyram (nitenpyram), acetamiprid (acetamiprid), thiamethoxam (thiamethoxam), thiacloprid, dinotefuran, clothianidin, etc .;
(6) Benzoylurea compounds Chlorfluazuron, bistrifluron, diafenthiuron, diflubenzuron, fluazuron, flucycloxuron, flufenoc Flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, triazuron, etc .;
(7) Phenylpyrazole compounds acetoprole, ethiprole, fiproni1, fiproni1, vaniliprole, pyriprole, pyrafluprole, etc .;
(8) Bt toxin insecticide, live spores and produced crystal toxins derived from Bacillus thuringiensis, and mixtures thereof;
(9) Hydrazine compounds Chromafenozide, halofenozide, methoxyfenozide, tebufenozide and the like;
(10) Organochlorine compounds Aldrin, dieldrin, dienochlor, endosulfan, methoxychlor, etc .;
(11) Natural insecticide machine oil, nicotine-sulfate;
(12) Other insecticides: avermectin-aver (B), bromopropylate, buprofezin, chlorphenapyr, cyromazine, DD (1,3-Dichloropropene), emamectin benzoate ( emamectin-benzoate, fenazaquin, flupyrazofos, hydroprene, metoprene, indoxacarb, metoxadiazone, milbemycin-A, pymetrozine , Pyridalyl, pyriproxyfen, spinosad, sulfluramid, tolfenpyrad, triazamate, flubendiamide, lepimectin, subpimectin Arsenic acid, Benclothiaz, Calcium cyanamide, Calcium polysulfide, chlordane, DDT, DSP, flufenerim, flonicamid, flurimidene (Flurimfen), formetanate, metam-ammonium, metam-sodium, methyl bromide, nidinotefuran, potassium oleate, prototri Fenbute, spiromesifen, sulfur, metaflumizone, spirotetramat, pyrifluquinazone, spinetram, chlorantraniliprole, cyan Traniliprol (Cyantraniliprole),
Etc.
Such other acaricides (acaricidal active ingredients) include, for example, acequinocyl, amitraz, benzoximate, bifenaate, phenisobromolate, chinomethionat , Chlorobenzilate, CPCBS (chlorfenson), clofentezine, cyflumetofen, kelofol, etoxazole, fenbutatin oxide, fenothiocarb, fenpyroxycarb (Fenpyroximate), fluacrypyrim, fluproxyfen, hexythiazox, propargite (BPPS), polynactins, polynactins, pyridaben, Pyrimidifen, tebufenpyrad, tetradifon, spirodiclofen, spiromesifen, spirotetramat, amidoflumet, cyenopyrafen, etc. It is done.
Examples of such other nematicides (nematicidal active ingredients) include, for example, DCIP, fosthiazate, levamisol hydrochloride, methamiisothiocyanate, morantel tartarate, imicyafos Etc.

  The application amount of the present control agent varies depending on weather conditions, formulation form, application time, application method, application place, target disease, target crop, etc., but per 10 ares of the present compound amount in the present control agent, Usually 1 to 500 g, preferably 2 to 200 g. Emulsions, wettable powders, suspensions and the like are usually diluted with water and applied. In this case, the concentration of the compound of the present invention after dilution is usually 0.0005 to 2% by weight, preferably 0.005 to 1. The powder, granules and the like are usually applied as they are without dilution. In the seed treatment, the amount of the compound of the present invention in the control agent of the present invention is usually 0.001 to 100 g, preferably 0.01 to 50 g per 1 kg seed.

  The control agent of the present invention can be used as a plant disease control agent in agricultural land such as fields, paddy fields, lawns, orchards. The control agent of the present invention can control diseases of the farmland in the farmland where the following “crop” and the like are cultivated.

Agricultural crops: corn, rice, wheat, barley, rye, oats, sorghum, cotton, soybeans, peanuts, buckwheat, sugar beet, rapeseed, sunflower, sugarcane, tobacco, vegetables, solanaceous vegetables (eggplant, tomato, pepper, pepper, potato 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, etc.,
Bridegroom,
Foliage plant,
Fruit trees; pears (apples, pears, Japanese pears, quince, quince, etc.), nuclear fruits (peaches, plums, nectarines, ume, sweet cherry, apricots, prunes, etc.), citrus (satsuma mandarin, orange, lemon, lime, grapefruit) ), Nuts (chestnut, walnut, hazel, almond, pistachio, cashew nut, macadamia nut, etc.), berries (blueberry, cranberry, blackberry, raspberry, etc.), grape, oyster, olive, loquat, banana, coffee, Date palm, coconut palm, etc.
Trees other than fruit trees: Cha, mulberry, flowering trees, street trees (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak, poplar, redwood, fu, sycamore, zelkova, black bean, peach tree, Tsuga, rat, pine, Spruce, yew) etc.

  The above `` crop '' is resistant to HPPD inhibitors such as isoxaflutol, ALS inhibitors such as imazetapyr and thifensulfuron methyl, EPSP synthase inhibitors, glutamine synthase inhibitors, herbicides such as bromoxynil, This includes crops granted by classical breeding methods or genetic engineering techniques.

  As an example of a “crop” to which resistance has been imparted by a classic breeding method, imidazolinone herbicide-resistant Clearfield (registered trademark) canola, such as imazetapil, and sulfonylurea-based ALS-inhibiting herbicide resistance such as thifensulfuron methyl There are STS soybeans. Examples of “crop” to which tolerance has been imparted by genetic engineering techniques include glyphosate and glufosinate-resistant corn varieties such as RoundupReady (registered trademark), RoundupReady2 (registered trademark), and LibertyLink (registered trademark). Already sold by name.

The “crop” includes, for example, a crop that can synthesize selective toxins known in the genus Bacillus by using genetic recombination technology.
Toxins expressed in such transgenic plants include insecticidal proteins from Bacillus cereus and Bacillus popirie; Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C from Bacillus thuringiensis Insecticidal protein such as δ-endotoxin, VIP1, VIP2, VIP3 or VIP3A; nematode-derived insecticidal protein; toxin produced by animals such as scorpion toxin, spider toxin, bee toxin or insect-specific neurotoxin; filamentous fungal toxin; plant Lectin; agglutinin; protease inhibitor such as trypsin inhibitor, serine protease inhibitor, patatin, cystatin, papain inhibitor; ribosome inactivating protein (RIP) such as lysine, corn-RIP, abrin, ruffin, saporin, bryodin; 3-hydroxysteroid oxidase, ecdysteroid Steroid metabolic enzymes such as UDP-glucosyltransferase and cholesterol oxidase; ecdysone inhibitor; HMG-COA reductase; ion channel inhibitor such as sodium channel and calcium channel inhibitor; juvenile hormone esterase; diuretic hormone receptor; stilbene synthase; Benzyl synthase; chitinase; glucanase and the like.

In addition, as toxins expressed in such genetically modified crops, Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C and other δ-endotoxin proteins, VIP1, VIP2, VIP3 or VIP3A and other insecticidal protein hybrids Toxins, partially defective toxins, modified toxins are also included. Hybrid toxins are produced by new combinations of different domains of these proteins using recombinant techniques. As a toxin lacking a part, Cry1Ab lacking a part of the amino acid sequence is known. In the modified toxin, one or more amino acids of the natural toxin are substituted.
Examples of these toxins and recombinant plants capable of synthesizing these toxins are EP-A-0 374 753, WO 93/07278, WO 95/34656, EP-A-0 427 529, EP-A-451 878. , WO 03/052073 and the like.
The toxins contained in these recombinant plants particularly confer resistance to Coleoptera pests, Diptera pests, and Lepidoptera pests.

  Also, genetically modified plants that contain one or more insecticidal pest resistance genes and express one or more toxins are already known, and some are commercially available. Examples of these transgenic plants include YieldGard® (a corn variety expressing Cry1Ab toxin), YieldGard Rootworm® (a corn variety expressing Cry3Bb1 toxin), YieldGard Plus® (Cry1Ab and Cry3Bb1 Corn varieties that express toxins), Herculex I® (corn varieties that express phosphinotricin N-astilyltransferase (PAT) to confer resistance to Cry1Fa2 toxin and glufosinate), NuCOTN33B (Cry1Ac toxin) Cotton varieties expressing), Bollgard I (registered trademark) (cotton varieties expressing Cry1Ac toxin), Bollgard II (registered trademark) (cotton varieties expressing Cry1Ac and Cry2Ab toxin), VIPCOT (registered trademark) (VIP toxin) Cotton varieties), NewLeaf (registered trademark) (potato varieties expressing Cry3A toxin), NatureGard (registered trademark) Agrisure (registered trademark) GT Advant Examples include age (GA21 glyphosate resistance trait), Agrisure (registered trademark) CB Advantage (Bt11 corn borer (CB) trait), Protecta (registered trademark), and the like.

The above “crop” includes those given the ability to produce an anti-pathogenic substance having a selective action using genetic recombination technology.
PR proteins and the like are known as examples of anti-pathogenic substances (PRPs, EP-A-0 392 225). Such anti-pathogenic substances and genetically modified plants that produce them are described in EP-A-0 392 225, WO 95/33818, EP-A-0 353 191 and the like.
Examples of anti-pathogenic substances expressed in such genetically modified plants include, for example, sodium channel inhibitors and calcium channel inhibitors (KP1, KP4, KP6 toxins produced by viruses, etc.) are known. Ion channel inhibitors; stilbene synthase; bibenzyl synthase; chitinase; glucanase; PR protein; peptide antibiotics, heterocyclic antibiotics, protein factors involved in plant disease resistance (called plant disease resistance genes, WO No. 03/000906)) and other anti-pathogenic substances produced by microorganisms.

Moreover, the above-mentioned “crop” is a line to which two or more kinds of traits related to herbicide resistance, pest resistance, disease resistance, etc. as described above are imparted using classical breeding technology or genetic recombination technology Also included are strains to which two or more properties of the parent strain are imparted by crossing genetically modified plants having similar or different properties.

Examples of plant diseases that can be controlled by the present invention include filamentous fungi and the like, and more specifically, the following diseases can be mentioned, but are not limited thereto.
Usually, this invention control method is performed by using this invention control agent by the method of applying this invention control agent mentioned above.

  Rice blast (Magnaporthe grisea), sesame leaf blight (Cochliobolus miyabeanus), blight (Rhizoctonia solani), idiot seedling (Gibberella fujikuroi), yellow dwarf (Sclerophthora macrospora); wheat powdery mildew (Erysiphe) graminis), red mold (Fusarium graminearum, F. avenacerum, F. culmorum, Microdochium nivale), rust (Puccinia striiformis, P. graminis, P. recondita), red snow rot (Micronectriella nivale), snow mold Nuclear disease (Typhula sp.), Bare smut (Ustilago tritici), Tilletia caries, Eye spot disease (Pseudocercosporella herpotrichoides), Leaf blight (Mycosphaerella graminicola), Blight (Stagonospora nodorum), Macular disease (Pyrenophora tritici-repentis), barley powdery mildew (Erysiphe graminis), red mold (Fusarium graminearum, F. avenacerum, F. culmorum, Microdochium nivale), rust (Puccinia striiformis, P. graminis, P. hordei) ),naked Blackhead disease (Ustilago nuda), cloud disease (Rhynchosporium secalis), reticular disease (Pyrenophora teres), spot disease (Cochliobolus sativus), leafy leaf disease (Pyrenophora graminea), Rhizoctonia genus Rhizoctonia solani; Citrus black spot (Diaporthe citri), common scab (Elsinoe fawcetti), fruit rot (Penicillium digitatum, P. italicum); apple monilia (Monilinia mali), rot (Valsa ceratosperma), powdery mildew (Podosphaera) leucotricha), spotted leaf disease (Alternaria alternata apple pathotype), black spot disease (Venturia inaequalis), anthrax (Glomerella cingulata); pear black spot disease (Venturia nashicola, V. pirina), black spot disease (Alternaria alternata Japanese pear pathotype) ), Red scab (Gymnosporangium haraeanum); peach blight (Monilinia fructicola), black scab (Cladosporium carpophilum), phomopsis sp. (Phomopsis sp.); Grape black scab ( Elsinoe ampelina), late rot (Glomerella cingulata), powdery mildew (Uncinula necator), rust (Phakopsora ampelopsidis), blacklot disease (Guignardia bidwellii), downy mildew (Plasmopara viticola); oyster anthracnose (Gloeosporium) kaki), leaf fall (Cercospora kaki, Mycosphaerella nawae); cucurbit (Colletotrichum lagenarium), powdery mildew (Sphaerotheca fuliginea), vine blight (Mycosphaerella melonis), vine split (Fusarium oxysporum), downy mildew Disease (Pseudoperonospora cubensis), plague (Phytophthora sp.), Seedling blight (Pythium sp.); Tomato ring-rot (Alternaria solani), leaf mold (Cladosporium fulvum), plague (Phytophthora infestans); brown eggplant Herpes disease (Phomopsis vexans), powdery mildew (Erysiphe cichoracearum); black spot disease of cruciferous vegetables (Alternaria japonica), white spot disease (Cercosporella brassicae), clubroot disease (Plasmodiophora parasitica), downy mildew (Peronos) pora parasitica); green onion rust (Puccinia allii), soybean purpura (Cercospora kikuchii), black scab (Elsinoe glycines), black spot (Diaporthe phaseolorum var. sojae), rust (Phakopsora pachyrhizi), green beans Colletotrichum lindemthianum groundnut black rot (Cercospora personata), brown spot (Cercospora arachidicola), silkworm (Sclerotium rolfsii); pea powdery mildew (Erysiphe pisi); potato summer plague (Alternaria solani) , Plague (Phytophthora infestans), half body wilt (Verticillium albo-atrum, V. dahliae, V. nigrescens); strawberry powdery mildew (Sphaerotheca humuli); tea net blast (Exobasidium reticulatum); white star disease (Elsinoe leucospila) ), Ring spot disease (Pestalotiopsis sp.), Anthracnose (Colletotrichum theae-sinensis) tobacco red streak (Alternaria longipes), powdery mildew (Erysiphe cichoracearum), anthracnose (Colletotrichum tabacum), Downy mildew (Peronospora tabacina), plague (Phytophthora nicotianae); brown spot of sugar beet (Cercospora beticola), leaf rot (Thanatephorus cucumeris), root rot (Thanatephorus cucumeris), black root (Aphanomyces sochlioides); Diseases (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa); brown spot of chrysanthemum (Septoria chrysanthemi-indici), white rust (Puccinia horiana); leaf blight of onion (Botrytis cinerea, B. byssoidea, B. squamosa), gray rot (Botrytis alli); botanytis squamosa, various crops of gray mold (Botrytis cinerea), sclerotia (Sclerotinia sclerotiorum); radish black spot (Alternaria brassicicola) Shirah's Dollar Spot Disease (Sclerotinia homeocarpa), Shiva Brown Patch Disease and Rhizoctonia solani; and Banana Sigatoka Disease (Mycosphaerella fijiensis, Mycosphaerella musicola).

Hereinafter, the present invention will be described in more detail with reference to production examples, formulation examples, and test examples.
First, the manufacture example of this invention compound is shown.

¹H-NMR (DMSO-D₆) δ: 1.16 (3H, t, J = 7.6 Hz), 2.51-2.56 (2H, m), 3.99 (3H, s), 4.41 (2H, d, J = 6.0 Hz), 6.71 (1H, s), 7.03-7.09 (4H, m), 7.34-7.39 (4H, m), 8.95 (1H, t, J = 6.0 Hz). Production Example 1
Mix 0.20 g of 3-ethyl-1-methylpyrazole-5-carboxylic acid, 0.42 g of 4- (4-trifluoromethoxyphenoxy) benzylamine hydrochloride, 0.69 g of BOP reagent, 0.46 g of triethylamine and 3 ml of DMF. And stirred at room temperature for 2 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to give N- [4- (4-trifluoromethoxyphenoxy) phenyl] methyl-3-ethyl-1-methylpyrazole-5-carboxylic acid amide (hereinafter referred to as the present compound). (Described as (1).) 0.42 g was obtained.
Compound (1) of the present invention

¹ H-NMR (DMSO-D ₆ ) δ: 1.16 (3H, t, J = 7.6 Hz), 2.51-2.56 (2H, m), 3.99 (3H, s), 4.41 (2H, d, J = 6.0 Hz ), 6.71 (1H, s), 7.03-7.09 (4H, m), 7.34-7.39 (4H, m), 8.95 (1H, t, J = 6.0 Hz).

¹H-NMR (DMSO-D₆) δ: 2.15 (3H, s), 3.98 (3H, s), 4.43 (2H, d, J = 6.0 Hz), 6.67 (1H, s), 7.09-7.14 (4H, m), 7.38 (2H, d, J = 8.5 Hz), 7.73 (2H, d, J = 8.9 Hz), 8.95 (1H, t, J = 6.2 Hz). Production Example 2
Mix 0.20 g of 1,3-dimethylpyrazole-5-carboxylic acid, 0.43 g of 4- (4-trifluoromethylphenoxy) phenylmethylamine hydrochloride, 0.76 g of BOP reagent, 0.51 g of triethylamine and 3 ml of DMF, Stir at room temperature for 3 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to give N- [4- (4-trifluoromethylphenoxy) phenyl] methyl-1,3-dimethylpyrazole-5-carboxylic acid amide (hereinafter referred to as the present compound (2). ) 0.49 g was obtained.
Compound (2) of the present invention

¹ H-NMR (DMSO-D ₆ ) δ: 2.15 (3H, s), 3.98 (3H, s), 4.43 (2H, d, J = 6.0 Hz), 6.67 (1H, s), 7.09-7.14 (4H , m), 7.38 (2H, d, J = 8.5 Hz), 7.73 (2H, d, J = 8.9 Hz), 8.95 (1H, t, J = 6.2 Hz).

¹H-NMR (DMSO-D₆) δ: 2.15 (3H, s), 3.97 (3H, s), 4.39 (2H, d, J = 5.9 Hz), 6.66 (1H, s), 6.96 (2H, d, J = 8.5 Hz), 7.01-7.06 (2H, m), 7.19-7.24 (2H, m), 7.31 (2H, d, J = 8.5 Hz), 8.91 (1H, t, J = 6.1 Hz). Production Example 3
0.20 g of 1,3-dimethylpyrazole-5-carboxylic acid, 0.31 g of 4- (4-fluorophenoxy) phenylmethylamine, 0.76 g of BOP reagent, 0.36 g of triethylamine and 3 ml of DMF were mixed, and 2 hours at room temperature. Stir. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to give N- [4- (4-fluorophenoxy) phenyl] methyl-1,3-dimethylpyrazole-5-carboxylic acid amide (hereinafter referred to as the present compound (3)). 0.31 g was obtained.
Compound (3) of the present invention

¹ H-NMR (DMSO-D ₆ ) δ: 2.15 (3H, s), 3.97 (3H, s), 4.39 (2H, d, J = 5.9 Hz), 6.66 (1H, s), 6.96 (2H, d , J = 8.5 Hz), 7.01-7.06 (2H, m), 7.19-7.24 (2H, m), 7.31 (2H, d, J = 8.5 Hz), 8.91 (1H, t, J = 6.1 Hz).

¹H-NMR (DMSO-D₆) δ: 1.16 (3H, t, J = 7.0 Hz), 2.53 (2H, q, J = 7.6 Hz), 3.99 (3H, s), 4.40 (2H, d, J = 5.8 Hz), 6.71 (1H, s), 6.96 (2H, d, J = 7.7 Hz), 7.02-7.06 (2H, m), 7.19-7.24 (2H, m), 7.32 (2H, d, J = 8.0 Hz), 8.93 (1H, t, J = 5.8 Hz). Production Example 4
Mix 0.20 g of 3-ethyl-1-methylpyrazole-5-carboxylic acid, 0.28 g of 4- (4-fluorophenoxy) phenylmethylamine, 0.69 g of BOP reagent, 0.33 g of triethylamine and 3 ml of DMF at room temperature. Stir for 2 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography to give N- [4- (4-fluorophenoxy) phenyl] methyl-3-ethyl-1-methylpyrazole-5-carboxylic acid amide (hereinafter referred to as the present compound (4)). ) 0.28 g was obtained.
The present compound (4)

¹ H-NMR (DMSO-D ₆ ) δ: 1.16 (3H, t, J = 7.0 Hz), 2.53 (2H, q, J = 7.6 Hz), 3.99 (3H, s), 4.40 (2H, d, J = 5.8 Hz), 6.71 (1H, s), 6.96 (2H, d, J = 7.7 Hz), 7.02-7.06 (2H, m), 7.19-7.24 (2H, m), 7.32 (2H, d, J = 8.0 Hz), 8.93 (1H, t, J = 5.8 Hz).

  Next, reference production examples are shown for production of the production intermediate of the compound of the present invention.

¹H-NMR (CDCl₃) δ: 5.60 (1H, s), 5.99 (1H, s), 7.08 (2H, d, J = 8.9 Hz), 7.11 (2H, d, J = 8.9 Hz), 7.63 (2H, d, J = 8.9 Hz), 7.84 (2H, d, J = 8.7 Hz).
水素化リチウムアルミニウム４．６gをＴＨＦ２００ｍｌに混合し、４−（４−トリフルオロメチルフェノキシ）ベンズアミド１７ｇとＴＨＦ５０ｍｌの混合物を室温で加え、ついで６５℃で２時間撹拌した。室温付近まで放冷した反応混合物に水４．６ｍｌ、２０％水酸化ナトリウム水溶液４．６ｍｌ及び水１４ｍｌを順次加え、セライト（登録商標）で濾過し、濾液を減圧下濃縮した。残渣にメタノール１００ｍｌ及び３６％塩酸６．１ｍｌを加えて減圧下で濃縮し、得られた残渣をヘキサンで洗浄して４−（４−トリフルオロメチルフェノキシ）フェニルメチルアミン塩酸塩１３ｇを得た。
４−（４−トリフルオロメチルフェノキシ）フェニルメチルアミン塩酸塩

¹H-NMR (DMSO-D₆) δ: 4.04 (2H, s), 7.14 (2H, d, J = 8.7 Hz), 7.18 (2H, d, J = 8.5 Hz), 7.63 (2H, d, J = 8.5 Hz), 7.76 (2H, d, J = 8.7 Hz), 8.64 (3H, s). Reference production example 1
A mixture of 10 g of 4-hydroxybenzamide, 16 g of 4-fluoro-1-trifluoromethylbenzene, 36 g of cesium carbonate and 200 ml of DMF was stirred at 120 ° C. for 16 hours. Water was added to the reaction mixture allowed to cool to near room temperature, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with 10% aqueous sodium hydroxide solution, water, 5% hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was washed with hexane and dried to obtain 13 g of 4- (4-trifluoromethylphenoxy) benzamide.
4- (4-Trifluoromethylphenoxy) benzamide

¹ H-NMR (CDCl ₃ ) δ: 5.60 (1H, s), 5.99 (1H, s), 7.08 (2H, d, J = 8.9 Hz), 7.11 (2H, d, J = 8.9 Hz), 7.63 ( 2H, d, J = 8.9 Hz), 7.84 (2H, d, J = 8.7 Hz).
4.6 g of lithium aluminum hydride was mixed with 200 ml of THF, a mixture of 17 g of 4- (4-trifluoromethylphenoxy) benzamide and 50 ml of THF was added at room temperature, and then stirred at 65 ° C. for 2 hours. 4.6 ml of water, 4.6 ml of 20% aqueous sodium hydroxide solution and 14 ml of water were sequentially added to the reaction mixture allowed to cool to near room temperature, filtered through Celite (registered trademark), and the filtrate was concentrated under reduced pressure. To the residue, 100 ml of methanol and 6.1 ml of 36% hydrochloric acid were added and concentrated under reduced pressure. The resulting residue was washed with hexane to obtain 13 g of 4- (4-trifluoromethylphenoxy) phenylmethylamine hydrochloride.
4- (4-Trifluoromethylphenoxy) phenylmethylamine hydrochloride

¹ H-NMR (DMSO-D ₆ ) δ: 4.04 (2H, s), 7.14 (2H, d, J = 8.7 Hz), 7.18 (2H, d, J = 8.5 Hz), 7.63 (2H, d, J = 8.5 Hz), 7.76 (2H, d, J = 8.7 Hz), 8.64 (3H, s).

¹H-NMR (CDCl₃) δ: 1.61 (2H, br s), 3.87 (2H, s), 6.95-7.00 (4H, m), 7.16 (2H, d, J = 8.6 Hz), 7.31 (2H, d, J = 8.3 Hz). Reference production example 2
419 mg of 4- (4-trifluoromethoxyphenoxy) benzonitrile was added to 1 ml of THF, 1 ml of a lithium aluminum hydride solution (2.0 M) was added dropwise at 0 ° C., and the mixture was stirred at room temperature for 2 hours. To the reaction mixture, 1 ml of ethanol, 2 ml of water and 1 ml of 15% aqueous sodium hydroxide solution were successively added dropwise at 0 ° C. The reaction mixture was filtered through Celite (registered trademark), and the filtrate was concentrated by centrifugation under reduced pressure. Saturated saline was added to the resulting residue and the mixture was extracted with MTBE. The organic layer was dried over magnesium sulfate and concentrated by centrifugation under reduced pressure to obtain 361 mg of 4- (4-trifluoromethoxyphenoxy) phenylmethylamine.
4- (4-Trifluoromethoxyphenoxy) phenylmethylamine

¹ H-NMR (CDCl ₃ ) δ: 1.61 (2H, br s), 3.87 (2H, s), 6.95-7.00 (4H, m), 7.16 (2H, d, J = 8.6 Hz), 7.31 (2H, d, J = 8.3 Hz).

  Next, formulation examples are shown. In addition, a part represents a weight part.

Formulation Example 1
The wettable powder is obtained by thoroughly pulverizing and mixing 50 parts of any one of the compounds (1) to (4) of the present invention, 3 parts of calcium lignin sulfonate, 2 parts of magnesium lauryl sulfate and 45 parts of synthetic silicon hydroxide. .

Formulation Example 2
20 parts of any one of the compounds (1) to (4) 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, followed by a wet pulverization method. After that, 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 and mixed to obtain a flowable preparation. Get.

Formulation Example 3
A powder is obtained by thoroughly pulverizing and mixing 2 parts of any one of the compounds (1) to (4) of the present invention, 88 parts of kaolin clay and 10 parts of talc.

Formulation Example 4
An emulsion is obtained by thoroughly mixing 5 parts of any one of the compounds (1) to (4) of the present invention, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 75 parts of xylene. .

Formulation Example 5
After thoroughly mixing 2 parts of any one of the compounds (1) to (4) of the present invention, 1 part of synthetic hydrous hydroxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay, water is added. Knead well and granulate dry to obtain granules.

Formulation Example 6
Mix 10 parts of any one of the compounds (1) to (4) of the present invention, 35 parts of white carbon containing 50 parts of polyoxyethylene alkyl ether sulfate ammonium salt and 55 parts of water, and pulverize them by wet pulverization. To obtain a flowable formulation.

Next, test examples show that the compounds of the present invention are useful for controlling plant diseases.
The control effect is obtained by visually observing the area of the lesion on the test plant at the time of the survey, and comparing the area of the lesion on the plant treated with the compound of the present invention and the area of the lesion on the untreated plant. evaluated.

Test example 1
Radish black spot disease prevention effect test (Alternaria brassicicola)
A plastic pot was filled with sand loam, seeded with Japanese radish (variety; early 40 days), and grown in a greenhouse for 5 days. After making this invention compound (1)-(3) and (4) into a flowable formulation according to the formulation example 6, it dilutes with water, it is made predetermined concentration (500 ppm), and foliage is sprayed so that it may adhere enough to the said radish leaf surface. did. After spraying, the plants were air-dried and spray-inoculated with an aqueous suspension of radish black spot fungus spores. After inoculation, it was first placed at 24 ° C. under high humidity for 1 day and then placed in a greenhouse for 3 days, and then the lesion area was examined. As a result, the lesion area in the plant which processed this invention compound (1)-(3) and (4) was 30% or less of the lesion area in an untreated plant.

Test example 2
Cucumber gray mold prevention effect test (Botrytis cinerea)
A plastic pot was filled with sandy loam, cucumber (variety: Sagamihanjiro) was sown and grown in a greenhouse for 12 days. After making this invention compound (1), (3) and (4) into a flowable formulation according to Formulation Example 6, dilute with water to a predetermined concentration (500 ppm), and spray with foliage to adhere well to the cucumber leaf surface. did. After spraying, the plants were air-dried, and a PDA medium containing spores of cucumber gray mold was placed on the cucumber leaf surface. After inoculation, the lesion area was examined after 5 days in a humid environment at 12 ° C. As a result, the lesion area on the plant treated with the compounds (1), (3) and (4) of the present invention was 30% or less of the lesion area on the untreated plant.

Test example 3
Rice blast prevention effect test (Magnaporthe grisea)
A plastic pot was filled with soil, rice (cultivar; Nihonbare) was sown and grown in a greenhouse for 12 days. The compounds (1) to (3) and (4) of the present invention were made into a flowable preparation according to Preparation Example 6 and then diluted with water to a predetermined concentration (500 ppm) so that the foliage was sufficiently attached to the rice leaf surface. Scattered. After spraying, the plants were air-dried, and a pot having rice blast-affected leaves was left around the sprayed plants. All the rice plants were placed under high humidity only at night, and the lesion area was examined 5 days after the inoculation. As a result, the lesion area in the plant which processed this invention compound (1)-(3) and (4) was 30% or less of the lesion area in an untreated plant.

Test example 4
Cucumber downy mildew treatment effect test (Pseudoperonospora cubensis)
A plastic pot was filled with sandy loam, 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. under high humidity for 1 day, and then air-dried to obtain a cucumber downy mildew-infected seedling. (1) to (3) and (4) were 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 leaf surface of the cucumber seedling. . After spraying, the plants were air-dried, placed in a greenhouse at 23 ° C. for 5 days, and further placed at 23 ° C. and humid for 1 day, and then the lesion area was examined. As a result, the lesion area in the plant treated with (1) to (3) and (4) was 30% or less of the lesion area in the untreated plant.

Test Example 5
Tomato plague prevention effect test (Phytophthora infestans)
A plastic pot was filled with sand loam, seeded with tomato (variety: patio), and grown in a greenhouse for 20 days. After making this invention compound (1)-(3) and (4) into a flowable formulation according to the formulation example 6, it dilutes with water to make predetermined concentration (500 ppm), and it adheres enough to the leaf surface of the said tomato seedling. The foliage was sprayed. After air-dried to such an extent that the diluted solution on the leaf surface was dried, the suspension was spray-inoculated with an aqueous suspension of tomato plague fungus spores. After inoculation, it was first placed at 23 ° C. under high humidity for 1 day and further cultivated in a greenhouse for 4 days, and then the lesion area was examined. As a result, the lesion area in the plant which processed this invention compound (1)-(3) and (4) was 30% or less of the lesion area in an untreated plant.

Test Example 6
Wheat red rust prevention effect test (Puccinia triticina)
A plastic pot was filled with sand loam, wheat (cultivar: Shirogane) was sown and grown in a greenhouse for 10 days. The compound (2), (3) and (4) 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 attached to the leaf surface of the wheat. Scattered. Five days later, wheat spores were sprinkled with spores and inoculated. After inoculation, the lesion area was examined after being placed at 18 ° C. in a dark and humid environment for 1 day and further under illumination for 9 days. As a result, the lesion area in the plant which processed this invention compound (2), (3) and (4) was 30% or less of the lesion area in an untreated plant.

Test Example 7
Test for prevention of kidney bean nuclear disease (Sclerotinia sclerotiorum)
A plastic pot was stuffed with sand loam, seeded with green beans (variety; Nagatake peas) and grown in a greenhouse for 8 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 (500 ppm), and sprayed on the foliage so as to adhere well to 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 the inoculation, all kidney beans were left under high humidity only at night, and the lesion area was examined 5 days after the inoculation. As a result, the lesion area in the plant treated with the compound (2) of the present invention was 30% or less of the lesion area in the untreated plant.

Test Example 8
Wheat leaf blight prevention effect test (Septoria tritici)
A plastic pot was filled with sandy loam, wheat (cultivar: Apogee) was sown and grown in a greenhouse for 10 days. After making this invention compound (1)-(3) and (4) into a flowable formulation according to the formulation example 6, it dilutes with water, it is made a predetermined density | concentration (500 ppm), and foliage so that it may adhere enough to the leaf surface of the said wheat Scattered. After spraying, the plants were air-dried, and after 2 days, sprayed with a water suspension of wheat leaf blight fungus spores. After the inoculation, the area was first placed under a high humidity of 18 ° C. for 3 days and further under illumination for 14 to 18 days, and then the lesion area was examined. As a result, the lesion area in the plant which processed this invention compound (1)-(3) and (4) was 30% or less of the lesion area in an untreated plant.

Test Example 9
Cucumber powdery mildew prevention effect test (Sphaerotheca furiginea)
A plastic pot was filled with sandy loam, cucumber (variety: Sagamihanjiro) was sown and grown in a greenhouse for 12 days. Thereafter, the compounds (1), (3) and (4) of the present invention are made into a flowable preparation according to Preparation Example 6 and then diluted with water to a predetermined concentration (500 ppm) so as to sufficiently adhere to the leaf surface of the cucumber. The foliage was sprayed on the ground. After spraying, the plants were air-dried and sprinkled with spores of pathogenic bacteria. After inoculation, it was placed in a 23 ° C. greenhouse for 10 days, and then the lesion area was examined. As a result, the lesion area in the plant which processed this invention compound (1), (3) and (4) was 30% or less of the lesion area in an untreated plant.

Claims (4)

Formula (I)

[Where,
R ¹ represents a methyl group, R ² represents a fluorine atom or a trifluoromethyl group, or R ¹ represents an ethyl group, and R ² represents a fluorine atom or a trifluoromethoxy group. ]
An amide compound represented by   A plant disease control agent comprising the amide compound according to claim 1 as an active ingredient.   A method for controlling plant diseases comprising a step of treating an effective amount of the amide compound according to claim 1 to a plant or soil.   Use of the amide compound according to claim 1 for controlling plant diseases by treating the plant or soil.