JP2019151553A - Oxadiazole compound and use thereof - Google Patents

Abstract

To provide a compound having excellent control effect on plant diseases.SOLUTION: A compound represented by formula (1) in the figure (where X represents a C3-C5 alkyl group or NRR; Rrepresents a C1-C3 alkyl group; Rrepresents a C2-C3 alkyl group; and R, R, Rand Reach independently represent a hydrogen atom or a fluorine atom) has excellent control effect on plant diseases.SELECTED DRAWING: None

Description

  The present invention relates to oxadiazole compounds and uses thereof.

  Conventionally, various compounds have been developed to control plant diseases (see Patent Document 1).

JP 63-162680 A

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

〔式中、
ＸはＣ３−Ｃ５アルキル基、又はＮＲ¹Ｒ²を表し、
Ｒ¹はＣ１−Ｃ３アルキル基を表し、
Ｒ²はＣ２−Ｃ３アルキル基を表し、
Ｒ³、Ｒ⁴、Ｒ⁵及びＲ⁶はそれぞれ独立して水素原子又はフッ素原子を表す。〕
で示される化合物（以下、本発明化合物と記す）。
〔２〕 Ｒ³、Ｒ⁴、Ｒ⁵及びＲ⁶が水素原子である、〔１〕に記載の化合物。
〔３〕 〔１〕又は〔２〕に記載の化合物を含有する植物病害防除剤（以下、本発明防除剤とも記す）。
〔４〕 〔１〕又は〔２〕に記載の化合物の有効量を植物又は土壌に処理することによる、植物病害の防除方法。
〔５〕 植物病害を防除するための、〔１〕又は〔２〕に記載の化合物の使用。 As a result of studies to find a compound having an excellent control effect against plant diseases, the present inventors have found that the compound represented by the following formula (1) has an excellent control effect against plant diseases. .
That is, the present invention is as follows.
[1] Formula (1)

[Where,
X represents a C3-C5 alkyl group, or NR ¹ R ² ;
R ¹ represents a C1-C3 alkyl group,
R ² represents a C2-C3 alkyl group,
R ³ , R ⁴ , R ⁵ and R ⁶ each independently represent a hydrogen atom or a fluorine atom. ]
(Hereinafter referred to as the present compound).
[2] The compound according to [1], wherein R ³ , R ⁴ , R ⁵ and R ⁶ are hydrogen atoms.
[3] A plant disease control agent comprising the compound according to [1] or [2] (hereinafter also referred to as the present control agent).
[4] A method for controlling plant diseases by treating a plant or soil with an effective amount of the compound according to [1] or [2].
[5] Use of the compound according to [1] or [2] for controlling plant diseases.

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

The substituents in this specification will be described.
Examples of the C3-C5 alkyl group include propyl group, isopropyl group, 1,1-dimethylpropyl group, 1,2-dimethylpropyl group, 2,2-dimethylpropyl group, 1-ethylpropyl group, butyl group, isobutyl. Group, sec-butyl group, tert-butyl group, 1-methylbutyl group, 2-methylbutyl group, and pentyl group, and X is propyl group, isopropyl group, butyl group, isobutyl group, and tert-butyl group. preferable.
Examples of the C1-C3 alkyl group include a methyl group, an ethyl group, a propyl group, and an isopropyl group, and R ¹ is preferably a methyl group.
Examples of the C2-C3 alkyl group include an ethyl group, a propyl group, and an isopropyl group, and R ² is preferably an ethyl group.

  When this invention compound has an asymmetric center, each optical isomer and the mixture containing them in arbitrary ratios are also contained in this invention compound.

  The compound of the present invention is mixed with an acid such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid or benzoic acid, thereby adding an acid addition salt such as hydrochloride, sulfate, nitrate, phosphate, acetate or benzoate. May form.

  Examples of the compound of the present invention include the following compounds.

The compound of the present invention, wherein X is a C3-C5 alkyl group.
In the compounds of the present invention, a compound wherein X is a propyl group, an isopropyl group or a butyl group.
The compound of the present invention, wherein X is a C3-C5 alkyl group and R ³ , R ⁴ , R ⁵ and R ⁶ are hydrogen atoms.
The compound of the present invention, wherein X is a propyl group, isopropyl group or butyl group, and R ³ , R ⁴ , R ⁵ and R ⁶ are hydrogen atoms.
In the compounds of the present invention, a compound wherein X is NR ¹ R ² .
The compound of the present invention, wherein X is NR ¹ R ² , and R ³ , R ⁴ , R ⁵ and R ⁶ are hydrogen atoms.
In the compounds of the present invention, a compound wherein X is a propyl group.
In the compounds of the present invention, a compound wherein X is an isopropyl group.
In the compounds of the present invention, a compound wherein X is a butyl group.
The compound of the present invention, wherein R ¹ is a methyl group and R ² is an ethyl group.
The compound of the present invention, wherein X is NR ¹ R ² , R ¹ is a methyl group, and R ² is an ethyl group.

  Next, the manufacturing method of this invention compound is demonstrated.

  The compound of the present invention can be produced by the following production method or the like.

〔式中の記号は前記と同じ意味を表す。〕
反応は、通常溶媒中で行われる。反応に用いられる溶媒としては、例えば、ｎ−ヘキサン、シクロヘキサン、トルエン、キシレン等の炭化水素（以下、炭化水素類と記す。）、ジエチルエーテル、テトラヒドロフラン（以下、ＴＨＦと記す。）、１，４−ジオキサン、エチレングリコールジメチルエーテル、メチルｔｅｒｔ−ブチルエーテル、ジイソプロピルエーテル等のエーテル（以下、エーテル類と記す。）、クロロホルム、ジクロロメタン、クロロベンゼン等のハロゲン化炭化水素（以下、ハロゲン化炭化水素類と記す。）、Ｎ，Ｎ−ジメチルホルムアミド（以下、ＤＭＦと記す。）、１，３−ジメチル−２−イミダゾリジノン、Ｎ−メチルピロリドン等のアミド（以下、アミド類と記す。）、酢酸エチル、酢酸メチル等のエステル（以下、エステル類と記す。）、アセトニトリル、プロピオニトリル等のニトリル（以下、ニトリル類と記す。）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例えば、トリエチルアミン、ピリジン、２，２’−ビピリジン、ジアザビシクロウンデセン等の有機塩基（以下、有機塩基類と記す。）、炭酸ナトリウム、炭酸カリウム等のアルカリ金属炭酸塩（以下、アルカリ金属炭酸塩類と記す。）、炭酸水素ナトリウムなどのアルカリ金属炭酸水素塩（以下、アルカリ金属炭酸水素塩類と記す。）、水素化ナトリウム等のアルカリ金属水素化物（以下、アルカリ金属水素化物類と記す。）及びその混合物が挙げられる。
化合物（Ａ１）は塩の形態であってもよい。化合物（Ａ１）の塩としては例えば、塩酸塩及び硫酸塩が挙げられる。
反応には、化合物（Ａ１）１モルに対して、化合物（Ａ２）が通常１〜１０モルの割合、塩基が通常１〜２０モルの割合で用いられる。
反応温度は通常−２０〜１５０℃の範囲内である。反応時間は通常０．１〜１２０時間の範囲内である。
反応終了後は、反応混合物に水を加え、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。
化合物（Ａ１）は、国際公開第２０１６／０３１８１５号に記載の方法に準じて製造することができる。
化合物（Ａ２）は、公知である。 Manufacturing method A
The compound of the present invention comprises a compound represented by formula (A1) (hereinafter referred to as compound (A1)) and a compound represented by formula (A2) (hereinafter referred to as compound (A2)) in the presence of a base. It can manufacture by making it react.

[The symbols in the formula have the same meaning as described above. ]
The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include hydrocarbons such as n-hexane, cyclohexane, toluene and xylene (hereinafter referred to as hydrocarbons), diethyl ether, tetrahydrofuran (hereinafter referred to as THF), and 1,4. -Ethers such as dioxane, ethylene glycol dimethyl ether, methyl tert-butyl ether and diisopropyl ether (hereinafter referred to as ethers), halogenated hydrocarbons such as chloroform, dichloromethane and chlorobenzene (hereinafter referred to as halogenated hydrocarbons). N, N-dimethylformamide (hereinafter referred to as DMF), amides such as 1,3-dimethyl-2-imidazolidinone and N-methylpyrrolidone (hereinafter referred to as amides), ethyl acetate, methyl acetate Esters such as (hereinafter referred to as esters), a Tonitoriru, nitriles such as propionitrile (hereinafter, referred to as nitriles.) And mixtures thereof.
Examples of the base used in the reaction include organic bases such as triethylamine, pyridine, 2,2′-bipyridine, diazabicycloundecene (hereinafter referred to as organic bases), alkali metal carbonates such as sodium carbonate and potassium carbonate. Salts (hereinafter referred to as alkali metal carbonates), alkali metal hydrogen carbonates such as sodium hydrogen carbonate (hereinafter referred to as alkali metal hydrogen carbonates), alkali metal hydrides such as sodium hydride (hereinafter referred to as alkali metals). Hydrides) and mixtures thereof.
Compound (A1) may be in the form of a salt. Examples of the salt of compound (A1) include hydrochloride and sulfate.
In the reaction, with respect to 1 mol of compound (A1), compound (A2) is usually used at a ratio of 1 to 10 mol, and base is usually used at a ratio of 1 to 20 mol.
The reaction temperature is usually in the range of -20 to 150 ° C. The reaction time is usually in the range of 0.1 to 120 hours.
After completion of the reaction, the compound of the present invention can be isolated by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.
Compound (A1) can be produced according to the method described in International Publication No. 2016/031815.
Compound (A2) is known.

〔式中の記号は前記と同じ意味を表す。〕 Manufacturing method B
A compound represented by the formula (1-A) (hereinafter referred to as the compound (1-A)) can be produced according to the following scheme.

[The symbols in the formula have the same meaning as described above. ]

  In this production method, the compound (1-A) is produced from the first step of producing a compound represented by the formula (A3) from the compound (A1) (hereinafter referred to as the compound (A3)) and the compound (A3). Including a second step.

First, the first step will be described.
Compound (A3) can be produced by reacting compound (A1) with phosgene, diphosgene or triphosgene in the presence of a base. The reaction can be performed according to the method described in Synthetic Communications, 2007, 37, 1037.
After completion of the reaction, the compound (A3) can be used as it is in the second step without removing it, or the residue obtained by concentrating the reaction mixture can be used as it is in the second step.

Next, the second step will be described.
Compound (1-A) can be produced by reacting compound (A3) with a compound represented by formula (A4) (hereinafter referred to as compound (A4)).
The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, and mixtures thereof.
In the reaction, compound (A4) is usually used at a ratio of 1 to 10 mol with respect to 1 mol of compound (A3).
The reaction temperature is usually in the range of -20 to 100 ° C. The reaction time is usually in the range of 0.1 to 120 hours.
After completion of the reaction, the compound (1-A) 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.
Compound (A4) is publicly known.

〔式中、記号は前記と同じ意味を表す。〕 Manufacturing method C
The compound of the present invention can also be produced from a compound represented by formula (A5) (hereinafter referred to as compound (A5)) according to the following scheme.

[Wherein the symbols have the same meaning as described above. ]

  In this production method, the first step of producing a compound represented by the formula (A6) from the compound (A5) (hereinafter referred to as the compound (A6)), a compound represented by the formula (A7) from the compound (A6) ( Hereinafter, the second step of producing the compound (A7)) and the third step of producing the compound of the present invention from the compound (A7) are included.

First, the first step will be described.
Compound (A6) can be produced by reacting compound (A5) with compound (A2) in the presence of a base. The reaction can be carried out according to the method described in Production Method A.
Compound (A5) is publicly known.

Next, the second step will be described.
Compound (A7) can be produced by reacting compound (A6) with hydroxylamine. The reaction can be carried out according to the method described in Organic Letters, 2014, 16, 892.

Next, the third step will be described.
The compound of the present invention can be produced by reacting compound (A7) with trifluoroacetic anhydride in the presence of a base.
The reaction is usually performed in a solvent. Examples of the solvent used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, alcohols such as methanol and ethanol (hereinafter referred to as alcohols), and these. A mixture is mentioned.
Examples of the base used in the reaction include organic bases, alkali metal carbonates, alkali metal hydrogen carbonates, alkali metal hydrides, and mixtures thereof.
In the reaction, with respect to 1 mol of the compound (A7), the trifluoroacetic anhydride is usually used at a ratio of 1 to 10 mol and the base at a ratio of 1 to 10 mol.
The reaction temperature is usually in the range of -20 to 150 ° C. The reaction time is usually in the range of 0.1 to 120 hours.
After completion of the reaction, the compound of the present invention can be isolated by performing post-treatment operations such as adding water to the reaction mixture, extracting with an organic solvent, and drying and concentrating the organic layer.

  The control agent of the present invention is usually prepared by mixing the compound of the present invention with a solid carrier, a liquid carrier, and / or a surfactant, and if necessary, adding auxiliary agents for preparation such as a fixing agent, a dispersing agent and a stabilizer. Wettable powder, wettable powder, flowable powder, granule, dry flowable powder, emulsion, aqueous liquid, oil, smoke, aerosol, microcapsule, poison bait, resin preparation, shampoo, paste It is formulated into preparations, foams, carbon dioxide preparations, tablets 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 thereof include fine powders or granular materials such as calcium carbonate and hydrated silica.
Examples of the liquid carrier include water, alcohols, ketones (eg, acetone, methyl ethyl ketone, cyclohexanone), aromatic hydrocarbons (eg, benzene, toluene, xylene, ethylbenzene, methylnaphthalene), aliphatic hydrocarbons ( Examples thereof include n-hexane, kerosene), esters, nitriles, ethers, amides, and halogenated hydrocarbons.

  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 alcohols. Derivatives.

  Other formulation adjuvants include, for example, fixing agents, dispersants, and stabilizers. Specifically, casein, gelatin, polysaccharides (eg, starch, arabic gum, cellulose derivatives, alginic acid), lignin derivatives, bentonite. , Sugars, synthetic water-soluble polymers (eg, polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acids), isopropyl acid phosphate, 2,6-di-tert-butyl-4-methylphenol, 2-tert-butyl-4- Examples thereof include mixtures of methoxyphenol and 3-tert-butyl-4-methoxyphenol, vegetable oils, mineral oils, fatty acids and esters thereof.

  Further, the compound of the present invention may be used for controlling plant diseases by mixing with oils such as mineral oil and vegetable oil, or surfactants. Oils that can be used in admixture, or surfactants include Nimbus (registered trademark), Assist (registered trademark), Aureo (registered trademark), Iharol (registered trademark), Silwet L-77 (registered trademark), BreakThru ( (Registered trademark), Sundance II (registered trademark), Induce (registered trademark), Penetrator (registered trademark), AgriDex (registered trademark), Lutensol A8 (registered trademark), NP-7 (registered trademark), Triton (registered trademark), Nufilm (Registered trademark), Emulator NP7 (registered trademark), Emulad (registered trademark), TRITON X 45 (registered trademark), AGRAL 90 (registered trademark), AGROTIN (registered trademark), ARPON (registered trademark), EnSpray N (registered trademark) And BANOLE (registered trademark).

The application amount of the compound of the present invention varies depending on weather conditions, formulation form, application time, application method, application location, target disease, target crop, etc., but the amount of the compound of the present invention in the control agent of the present invention is about 1000 m ^2. Usually, 1 to 500 g, preferably 2 to 200 g. Emulsions, wettable powders, suspensions and the like are usually diluted with water before use. 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 2% by weight, and powders, granules, etc. are usually applied as they are without dilution

The method of applying the compound of the present invention is not particularly limited as long as the compound of the present invention can be applied, but for example, treatment to plants such as foliage spraying, soil treatment, etc. Treatment, seed treatment such as seed disinfection, treatment of harmful arthropods, and the like.
When processing this invention compound to the foliage of a plant, or when processing to the soil which grows a plant, this invention compound is 1-500g normally per 1000m < ² > of soil. When treating seeds, the amount of the compound of the present invention in the present control agent is usually 0.001 to 100 g, preferably 0.01 to 50 g per 1 kg seed.
Emulsions, wettable powders, flowables and the like are usually treated by diluting with water and spraying. In this case, the concentration of the compound of the present invention is usually 0.0005 to 2% by weight. Powders, granules, etc. are usually processed without dilution.

  In addition, the compound of the present invention can be used as a plant disease control agent in agricultural land such as fields, paddy fields, lawns, orchards. The compound of the present invention can control diseases of the cultivated land in cultivated lands where the following plants are cultivated. Moreover, this invention compound can control the harmful arthropod of the said agricultural field.

Agricultural crops: corn, rice, wheat, barley, rye, oats, sorghum, cotton, soybeans, peanuts, buckwheat, sugar beet, rapeseed, sunflower, sugarcane, tobacco, etc. Vegetables: eggplants (eggs, tomatoes, peppers, peppers, potatoes) Cucumber, pumpkin, zucchini, watermelon, melon, etc., cruciferous vegetables (radish, turnip, horseradish, coral rabi, Chinese cabbage, cabbage, mustard, broccoli, cauliflower, etc.), asteraceae vegetables ( Burdock, garlic, artichoke, lettuce, etc.), liliaceae vegetables (leek, onion, garlic, asparagus), celery vegetables (carrots, parsley, celery, American burdock etc.), red crustacean vegetables (spinach, chard, etc.), perilla Vegetables (Perilla, Mint, Basil) Etc.), strawberry, sweet potato, yam, taro, etc., flower bud, houseplant,
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 plants include genetically modified crops.

Examples of plant diseases that can be controlled by the compounds of the present invention include diseases derived from plant pathogens such as filamentous fungi and bacteria. Specific examples include, but are not limited to, the following: It is not a thing. The parenthesis indicates the scientific name of the pathogen causing the disease.
Rice blast (Magnaporthe grisea), sesame leaf blight (Cochliobolus miyabeanus), blight (Rhizoctonia solani), idiot seedling (Gibberella fujikuroi), yellow dwarf (Sclerophthora macrospora); wheat powdery mildew (Blumeriagraminis) ), Red mold (Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivale), yellow rust (Puccinia striiformis), black rust (Puccinia graminis), red rust (Puccinia recondita), red snow rot (Microdochium nival) Microdochium majus), Snow rot microbe nuclear disease (Typhula incarnata, Typhula ishikariensis), Bare smut (Ustilago tritici), Tuna scab (Tilletia caries, Tilletia controversa), Eye rot (Pseudocercosporella herpotrichoidesep), Leaf blight tritici), blight (Stagonospora nodorum), maculopathy (Pyrenophora tritici-repentis), Rhizoctonia solani, blight (Gaeuma) nnomyces graminis); Barley powdery mildew (Blumeria graminis), red mold (Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivale), yellow rust (Puccinia striiformis), black rust (Puccinia graminis), red rust Puccinia hordei), scab disease (Puccinia hordei), naked scab disease (Ustilago nuda), cloud disease (Rhynchosporium secalis), reticular disease (Pyrenophora teres), spot disease (Cochliobolus sativus), leafy disease (Pyrenophora graminea), Ramallaria leaf spot disease (Ramularia collo-cygni), Rhizoctonia solani (Rhizoctonia solani); Corn rust (Puccinia sorghi), Southern rust (Puccinia polysora), Soot disease (Setosphaeria turcica), Tropical Sexual rust (Physopella zeae), sesame leaf blight (Cochliobolus heterostrophus), anthracnose (Colletotrichum graminicola), gray leaf spot disease (Cercospora zeae-maydis), Brown spot disease (Kabatiella zeae), Faeosfaeria reef spot disease (Phaeosphaeria maydis), Stenocarpella maydis, Stenocarpella macrospora, Stokelot disease (Fusarium graminearum, Fusarium verticilioides, Colletotrichum graminicola), smut (Ustilago maydis); Downy mildew (Colletotrichum gossypii), White mold disease (Ramularia areola), Black spot disease (Alternaria macrospora, Alternaria gossypii), Black root rot disease (Thielaviopsis basicola) caused by Thielaviopsis spp .; Coffee rust (Hemileia vastatrix), Leaf spot Diseases (Cercospora coffeicola); Sclerotinia sclerotiorum, black spot disease (Alternaria brassicae), root rot disease (Phoma lingam); sugarcane rust disease (Puccinia melanocephela, Puccinia kuehnii), scab (Ustilago scamine) Sunflower rust (Puccinia helianthi), downy mildew (Plasmopara halstedii); citrus black spot (Diaporthe citri) , Common scab (Elsinoe fawcetti), fruit rot (Penicillium digitatum, Penicillium italicum), plague (Phytophthora parasitica, Phytophthora citrophthora); apple monilia (Monilinia mali), rot (Valsa ceratosperma), powdery mildew (Podosera) leucotricha), spotted leaf disease (Alternaria alternata apple pathotype), black spot disease (Venturia inaequalis), anthracnose (Glomerella cingulata), brown spot disease (Diplocarpon mali), ring rot (Botryosphaeria berengeriana), plague (Phytophtora cactorum); Pear black spot disease (Venturia nashicola, Venturia pirina), black spot disease (Alternaria alternata Japanese pear pathotype), red star disease (Gymnosporangium haraeanum); peach asteroid disease (Monilinia fructicola), black star disease (Cladosporium carpophilum), fomosis rot (Phomopsis sp.); Grape black rot (Elsinoe ampelina), late rot (Glomerella cingulata), powdery mildew (Uncinula necator), rust Phakopsora ampelopsidis), black lot disease (Guignardia bidwellii), downy mildew (Plasmopara viticola); oyster anthracnose (Gloeosporium kaki), deciduous disease (Cercospora kaki, Mycosphaerella nawae); cucurbit anthracnose (Colletotrichum lagenarium) , Powdery mildew (Sphaerotheca fuliginea), vine blight (Didymella bryoniae), brown spot (Corynespora cassiicola), vine split disease (Fusarium oxysporum), downy mildew (Pseudoperonospora cubensis), plague (Phytophthora sp.) Blight (Pythium sp.); Ring tomato (Alternaria solani), leaf mold (Cladosporium fulvum), mold mold (Pseudocercospora fuligena), plague (Phytophthora infestans), powdery mildew (Leveillula taurica); Brown spot disease (Phomopsis vexans), powdery mildew (Erysiphe cichoracearum); black spot disease of cruciferous vegetables (Alternaria japonica), white spot disease (Cercosporella brassicae), clubroot disease (Plasmodiophora brassicae), Peronospora parasitica; green onion rust (Puccinia allii); soybean purpura (Cercospora kikuchii), black scab (Elsinoe glycines), black spot (Diaporthe phaseolorum var. Sojae), rust (Phakopsora pachyrhizi), Brown rot (Corynespora cassiicola), anthrax (Colletotrichum glycines, Colletotrichum truncatum), leaf rot (Rhizoctonia solani), brown rot (Septoria glycines), spot disease (Cercospora sojina), sclerotia (Sclerotinia sclerotiorum) Powdery mildew (Microsphaera diffusa), stem rot (Phytophthora sojae), downy mildew (Peronospora manshurica), sudden death (Fusarium virguliforme); kidney bean sclerotia (Sclerotinia sclerotiorum), rust (Uromyces appendiculatus), horny spot Diseases (Phaeoisariopsis griseola), anthracnose (Colletotrichum lindemuthianum); groundnut black rot (Cercospora personata), brown spot (Cercospora arachidicola), silkworm (Sclerotium rolfsii); Powdery mildew (Erysiphe pisi); Potato summer plague (Alternaria solani), plague (Phytophthora infestans), scarlet rot (Phytophthora erythroseptica), powdery scab (Spongospora subterranea f. Sp. Subterranea), half body wilt Diseases (Verticillium albo-atrum, Verticillium dahliae, Verticillium nigrescens); Strawberry powdery mildew (Sphaerotheca humuli); Chamochi rice rot (Exobasidium reticulatum), White spot disease (Elsinoe leucospila), Ring spot disease (Pestalotiopsis sp.) Anthracnose (Colletotrichum theae-sinensis); tobacco red star disease (Alternaria longipes), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina), plague (Phytophthora nicotianae); sugar beet brown spot (Cercospora beticola) Leaf rot (Thanatephorus cucumeris), root rot (Thanatephorus cucumeris), black root disease (Aphanomyces cochlioides), rust (Uromyces betae); rose scab (Diplocarpon rosae), Powdery mildew (Sphaerotheca pannosa); Chrysanthemum leaf spot (Septoria chrysanthemi-indici); White rust (Puccinia horiana); Onion leaf spot (Botrytis cinerea, Botrytis byssoidea, Botrytis squamosa); Botrytis squamosa; Gray rot of various crops (Botrytis cinerea); Mycorrhizal sclerosis (Sclerotinia sclerotiorum); Radish black spot (Alternaria brassicicola); Sclerot's spot disease (Sclerotinia homoeocarpa) ), Shiba brown patch disease and large patch disease (Rhizoctonia solani); and banana Sigatoka disease (Mycosphaerella fijiensis, Mycosphaerella musicola).
Seed disease or early growth of various crops caused by Aspergillus, Penicillium, Fusarium, Gibberella, Tricoderma, Thielaviopsis, Rhizopus, Mucor, Corticium, Phoma, Rhizoctonia, and Diplodia Disease. Viral diseases of various crops mediated by Polymyxa genus or Olpidium genus.
Rice seed blight (Burkholderia plantarii); Cucumber spotted bacterial disease (Pseudomonas syringae pv. Lachrymans); Eggplant blight (Ralstonia solanacearum); Citrus scab (Xanthomonas citri); carotovora) etc.

Examples of harmful arthropods that can be controlled by the compounds of the present invention include the following.
Hemiptera: Japanese brown planthopper (Laodelphax striatellus), Japanese brown planthopper (Nilaparvata lugens), white-tailed planthopper (Sogatella furcifera), corn planter (Peregrinus maidis), yellow-spotted plant (Javesella pellucida), black-tailed squid (Delphacidae); Nephotettix cincticeps, Nephotettix virescens, Nephotettix nigropictus, Recilia dorsalis, Eki ca ), Corn Leaf Hopper (Dalbulus maidis), Cofana spectra, etc., Cicadellidae; Mahanarva posticata, Mahanarva fimbriolata, etc., Cercopidae; Aphis fabae, soybean aphids (Aphis glycines), cotton aphids (Aphis gossypii), European apple aphids (Aphis pomi), snowy aphids (Aphis spiraecola), peach aphids (Myzus persicae), wheat arasi , Radish aphids (Brevicoryne brassicae), Rosy apple aphid (Dysaphis plantaginea), black radish aphids (Lipaphis erysimi), tulip beetle aphids (Macrosiphum euphorbiae), potato beetle aphids (Aulacorthum solani), aphids Aphids (Rhopalosiphum padi), corn aphids (Rhopalosiphum maidis), citrus aphids (Toxoptera citricidus), peach beetles (Hyalopterus pruni), hyena aphids (Melanaph) is sacchari), Tetraneura nigriabdominalis, Ceratovacuna lanigera, Ariodomae such as Eriosoma lanigerum; Daktulosphaira vitifolill Leaf phylloxera (Phylloxera notabilis), Southern pecan leaf phylloxera (Phylloxera russellae) and other aphids (Phylloxeridae); ; Scotinophara lurida, Malayan rice black bug (Scotinophara coarctata), Nezara antennata, Eysarcoris aeneus, Eysarcoris ysori village Saxirah Hawk stink bug (Eysarcoris annamita), Wagtail bug (Halyomorpha halys), Southern stink bug (Nezara viridula), Brown stink bug (Euschistus heros), Red banded stink bug (Piezodorus guildinii), Oebalus pugnax Pentatomidae); Burrower brown bug (Scaptocoris castanea) and other hornworms (Cydnidae); ); Coleus punctiger, Leptoglossus australis, etc. (Coreidae); Blissus leucopterus) (Lygaeidae); Trigonotylus caelestialium, Stenotus rubrovittatus, Stenodema calcarata, ario des riode (Rygus) , Tobacco whitefly (Bemisia tabaci), Daleurodes citri, Aleurocanthus spiniferus, Aleurocanthus camelliae, Peleius eleyae, etc. (Abgrallaspis cyanophylli), Aonidiella aurantii, Nasimaru scale (Diaspidiotus perniciosus), Scarab scale (Pseudaulacaspis pentagona), Bamboo scale (Unaspis yanonensis), Diaspididae such as Unaspis citri; Coccidae such as Ceroplastes rubens; Icerya purchasi; Icerya purchasi; Icerya seychellarum Scales (Margarodidae); Phenacoccus solani, Phenacoccus solenopsis, Pterococcus kraunhiae, Planococcus comstocki, Ciococcus octocus (Pseudococcus calceolariae), Pseudodococcus longispinus, Tattlemy Lee bug (Brevennia rehi), etc., Pseudococcidae; Diaphorina citri; ioza erytreae), Pepylthalidae (Cacopsylla pyrisuga), Pepylthiaceae (Psylliduch), Pear psylla (Cacopsylla pyricola) Corythucha marmorata), Stephanitis nashi, Stephanitis pyrioides, and other species; Cimex lectularius, such as Cimicidae;

  Lepidoptera: Green moth (Chilo suppressalis), Darkheaded stem borer (Chilo polychrysus), White stem borer (Scirpophaga innotata), Scirpophaga incertulas, Rupela albina, Cnaphalocrocisis media, Cnaphalocrocisis medis Hacasino maiga (Marasmia exigua), Watano maiga (Notarcha derogata), Awa no maiga (Ostrinia furnacalis), European corn borer (Ostrinia nubilalis), Hydraula undalis, Herpetogramma rel tueter, Rice case worms (Nymphula depunctalis), Sugarcane borer (Diatraea saccharalis), etc. (Crambidae); , Shiloi Spodoptera exigua, Mythimna separata, Mamestra brassicae, Sesamia inferens, Spodoptera mauritia, Naranga aenescens opt, Safoptera ma exempta), Agrotis ipsilon, Tamanaginuiwa (Autographa nigrisigna), Echinocera (Plusia festucae), Soybean looper (Chrysodeixis includens), Trichoplusia spp. (Helicoverpa armigera), Helicobelpa genus such as American tobacco moth (Helicoverpa zea), Velvetbean caterpillar (Anticarsia gemmatalis), Cotton leafworm (Alabama argillacea), Hop vine borer (Hydraecia immanis), etc. (Noctuidae) P; ris rapae) and other white butterflies (Pieridae); Nashihimeshinsukui (Grapholita molesta), Sumomohimeshinshii (Grapholita dimorpha), Beansinkigaiga (Leguminivora glycinivorella), Azusayamamushiga (Matsumuraeses azukivora), apples Adoxophyes honmai, Chamonaki (Homona magnanima), Midrekakumonmonaki (Archips fuscocupreanus), Kodlinga (Cydia pomonella), Kanshashini Amaki (Tetramoera schistaceana), Bean Shoot Borer (Epinotiacd fruitbo) Tortricidae such as aurantiana; Caloptilia theivora; Phyllonorycter ringoniella; Gracillariidae; Carposinera miner (Carposucidae); Pseudomonas (Lyonetia clerkella), Pleifolia (Lyonetia prunifoliella), etc. (Lyonetiidae); Lymantria dispar (Europetis pseudoconspersa), etc. (Plutella xylostella), etc. (Pluteliidae); peach beetle (Anarsia lineatella); Hytitria cunea, etc. Arctiidae; Giant Sugarcane borer (Telchin licus), Castniidae; Castus insularis, etc. Geometridae); Limacodidae, such as Parasa lepida; Staphmopodidae, such as Stahmopoda masinissa; Sphingidae, such as Acherontia lachesis; Nokona feral, etc. Sesiidae; Hesperiidae such as Parnara guttata.

  Thysanoptera: Citrus thalis (Fripliniella occidentalis), Thrips palmi, Scirtothrips dorsalis, Thrips tabasa, Thrips tabasa, Thrips tabasa ), Thripidae such as Echinothrips americanus; Phlaeothripidae such as Haplothrips aculeatus.

  Diptera: Drosophila (Delia platura), onion flies (Delia antiqua), etc .; Anthomyiidae; Tomato leaf fly (Liriomyza sativae), bee leaf leaf fly (Liriomyza trifolii), leaf leaf fly (Chromatomyia horticola), and the like leaf fly family (Agromyzidae); ), Eggplant fly (Bactrocera latifrons), olive fruit fly (Bactrocera oleae), quinsland fruit fly (Bactrocera tryoni), Ceratitis capitata, etc. (Tephritidae); Hydrellia philippina, Hydrellia sasakii, and other species (Ephydridae); Drosophila suzukii, and other species; Drosophila suzukii; (Clogmia albipunctata) and other butterflies; Bradysia difformis and other species of black flies (Sciaridae); Diopsidae such as macrophthalma; Tipulidae such as Tipula aino, Common cranefly (Tipula oleracea), European cranefly (Tipula paludosa).

  Coleoptera: Western corn root worm (Diabrotica virgifera virgifera), Southern corn root worm (Diabrotica undecimpunctata howardi), Northern corn root worm (Diabrotica barberi), Mexican corn root worm (Diabrotica virgifera zeae), Banded cucumber beetle Diabrotica balteata), Cucurbit Beetle (Diabrotica speciosa), bean leaf beetle (Cerotoma trifurcata), tiger beetle (Oulema melanopus), cucumber leaf beetle (Aulacophora femoralis), pheasant leaf beetle (Phyllotreta striolata) et black flea beetle (Phyllotreta pusilla), Cabbage stem flea beetle (Psylliodes chrysocephala), Colorado potato beetle (Leptinotarsa decemlineata), rice beetle (Oulema oryzae), grape colaspis (Colaspis brunnea), corn flarebi Toru (Chaetocnema pulicaria), sweet potato beetle (Chaetocnema confi), potato flare beetle (Epitrix cucumeris), rice beetle (Dicladispa armigera), Grape Colaspis (Colaspis brunnea), southern corn leaf denetle (Sweet corn leaf denticle) Laccoptera quadrimacu), Chrysomelidae such as Epitrix hirtipennis; Seedcorn beetle (Stenolophus lecontei), Slender seedcorn beetle (Clivina impressifrons); Carabidae; Anomala ala rufocuprea), Anomala albopilosa, bean squirrel (Popillia japonica), nagachakogane (Heptophylla picea), European Chafer (Rhizotrogus majalis), black marsh squirrel (Tomarus gibbosus), holotrichia genus, hyllophia lob s abderus genus Diloboderus genus Scarabaeidae; cotton beetle (Araecerus coffeae), aphid weevil (Cylas formicarius), weevil (Euscepes postfasciatus), alfalfa weevil (Hypera post zoe) (Echinocnemus squameus), rice weevil (Lissorhoptrus oryzophilus), white-headed weevil (Rhabdoscelus lineatocollis), cotton weevil (Anthonomus grandis), sword weevil (Sphenophorus venatus), Southern Corn Billbug (Sphenophusweest stalk stalk) , Sugarcane weevil (Sphenophorus levis), Sabigo weevil (Scepticus griseus), Scoticus uniform weevil (Scepticus uniformis), Brazilian weevil (Zabrotes subfasciatus), pine beetle (Tomicus piniperda), Coffee Berry Borer (Hypothenemus hampei), Aracanthus genus such as Aracanthus mourei, culmidae (Curculionidae) such as cotton root borer (Eutinobothrus brasiliensis); Tribolium castaneum, ), Ladybirds such as Epilachna vigintioctopunctata (Coccinellidae); beetles such as Lyctus brunneus (Bostrychidae); Ptinidae; Cerambycidae; Melanotus okinawensis, Agriotes fuscicollis, Melanotus sp., Elousus sp. , Limonius sp., Conoderu s sp., Ctenicera sp.); Staphylinidae, such as Paederus fuscipes.

  Orthoptera: Orthooptera: Locusta migratoria, Moroccan locust (Dociostaurus maroccanus), Australian locust (Chortoicetes terminifera), Red-necked grasshopper (Nomadacris septemfasciata), Brown Locust (Locustana parustina, Locustana pardalina, Locustana pardalina) Italian Locust (Calliptamus italicus), Differential grasshopper (Melanoplus differentialis), Two striped grasshopper (Melanoplus bivittatus), Migratory grasshopper (Melanoplus sanguinipes), Red-Legged grasshopper (Melanoplus femurrubrum), Clearwinged grasshopper (Camnula pellucister) gregaria), Yellow-winged locust (Gastrimargus musicus), Spur-throated locust (Austracris guttulosa), Cobainago (Oxya yezoensis), Scarlet moth (Oxya japonica), Thai winged locust (Patanga succincta), etc. a ricidae (Gryllotalpidae) such as a africana; crickets (Gryllidae) such as European cricket (Acheta domesticus) and Teleogryllus emma; and Tettigoniidae such as Mormon cricket (Anabrus simplex).

  Hymenoptera: Ants such as Athalia rosae and Athalia japonica, Tenthredinidae; Fire ant (Solenopsis spp.), Brown leaf-cutting ant (Atta capiguara) Department (Formicidae) etc.

  Cockroaches (Blattodea): German cockroach (Blattellidae) such as Blattella germanica; Black cockroach (Periplaneta fuliginosa), American cockroach (Periplaneta americana), Greater cockroach (Periplaneta brunnea), Greater cockroach (B) Family (Blattidae); Yamato termite (Reticulitermes speratus), termite (Coptotermes formosanus), American ant termite (Incisitermes minor), scallop termite (Cryptotermes domesticus), taiwan termite (Odontotermes formosanus), hun Nen termis (Glyptotermes satsumensis), long term termite (Glyptotermes nakajimai), long term termite (Glyptotermes fuscus), large termite (Hodotermopsis sjostedti), long term termite (Coptotermes guangzhouensis), amami Loite (Reticulitermes namobei), Miyatake termite (Reticulitermes miyatakei), Japanese termite (Reticulitermes kanmonensis), Takasago termite (Nasutitermes takasagoensis), Ants termites (Pericapritermes nitobei), Shari termites (mu) termites (mu) termites ).

  Hereinafter, the present invention will be described more specifically with reference to production examples, formulation examples, and test examples. However, the present invention is not limited to these examples.

  In the present specification, Me represents a methyl group, Et represents an ethyl group, Pr represents a propyl group, i-Pr represents an isopropyl group, Bu represents a butyl group, and Pen represents a pentyl group.

本発明化合物１：
¹H-NMR (CDCl₃) δ: 8.06 (2H, d), 7.69 (2H, d), 2.37 (2H, t), 1.73-1.82 (2H, m), 1.02 (3H, t). Production Example 1-1
0.19 mL of butyryl chloride was added dropwise to a mixture of 0.40 g of 3- (4-aminophenyl) -5- (trifluoromethyl) -1,2,4-oxadiazole hydrochloride, 0.52 mL of triethylamine, and 100 mL of THF. And stirred at room temperature for 1 hour. After the reaction solution was filtered, the filtrate was concentrated under reduced pressure. Water was added to the obtained residue, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to obtain 0.37 g of the present compound 1 shown below.

The present compound 1:
¹ H-NMR (CDCl ₃ ) δ: 8.06 (2H, d), 7.69 (2H, d), 2.37 (2H, t), 1.73-1.82 (2H, m), 1.02 (3H, t).

で示される化合物において、Ｘが下記で示される化合物。 Production Example 1-2
The compounds produced according to the method described in Production Example 1-1 and the physical properties thereof are shown below.
Formula (2)

A compound represented by the following formula, wherein X is:

Compound 2 of the present invention (X: CH (CH ₃ ) ₂ ):
¹ H-NMR (CDCl ₃ ) δ: 8.07 (2H, d), 7.70 (2H, d), 2.48-2.59 (1H, m), 1.27 (6H, d).
Compound 3 of the present invention (X: CH ₂ CH ₂ CH ₂ CH ₃ ):
¹ H-NMR (CDCl ₃ ) δ: 8.06 (2H, d), 7.69 (2H, d), 2.39 (2H, t), 1.67-1.76 (2H, m.), 1.46-1.35 (2H, m), 0.95 (3H, t).
Compound 4 of the present invention (X: CH ₂ CH (CH ₃ ) ₂ ):
¹ H-NMR (CDCl ₃ ) δ: 8.07 (2H, d), 7.69 (2H, d), 7.21 (1H, br s), 2.21-2.27 (3H, m), 1.03 (6H, d).
Compound 5 of the present invention (X: C (CH ₃ ) ₃ ):
¹ H-NMR (CDCl ₃ ) δ: 8.07 (2H, d), 7.71 (2H, d), 7.45 (1H, br s), 1.33 (9H, s).
Compound 6 of the present invention (X: CH (CH ₃ ) CH ₂ CH ₂ CH ₃ ):
¹ H-NMR (CDCl ₃ ) δ: 8.07 (2H, d), 7.71 (2H, d), 2.41-2.32 (1H, m), 1.69-1.79 (1H, m), 1.33-1.51 (3H, m) , 1.25 (3H, d), 0.93 (3H, t)
Compound 7 of the present invention (X: C (CH ₃ ) ₂ CH ₂ CH ₃ ):
¹ H-NMR (CDCl ₃ ) δ: 8.07 (2H, d), 7.71 (2H, d), 7.42 (1H, br s), 1.66 (2H, q), 1.29 (6H, s), 0.92 (3H, t)
Compound 8 of the present invention (X: CH ₂ C (CH ₃ ) ₃ ):
¹ H-NMR (CDCl ₃ ) δ: 8.06 (2H, d), 7.68 (2H, d), 7.20 (1H, br s), 2.26 (2H, s), 1.11 (9H, s)
Compound 9 of the present invention (X: CH ₂ (CH ₂ CH ₃ ) ₂ ):
¹ H-NMR (CDCl ₃ ) δ: 8.07 (2H, d), 7.72 (2H, d), 2.02-2.09 (1H, m), 1.54-1.79 (4H, m), 0.96 (6H, t)
Compound 10 of the present invention (X: CH ₂ CH ₂ CH ₂ CH ₂ CH ₃ ):
¹ H-NMR (CDCl ₃ ) δ: 8.07 (2H, d), 7.69 (2H, d), 2.39 (2H, t), 1.71-1.78 (2H, m), 1.34-1.39 (4H, m), 0.89 -0.93 (3H, m)

本発明化合物１１：
¹H-NMR (CDCl₃) δ: 8.02 (2H, d), 7.56 (2H, d), 6.48 (1H, br s), 3.43 (2H, q), 3.03 (3H, s), 1.21 (3H, t) Production Example 2
To a mixture of 0.22 g of triphosgene and 10 mL of chloroform was added 400 mg of 3- (4-aminophenyl) -5- (trifluoromethyl) -1,2,4-oxadiazole hydrochloride, 0.42 mL of triethylamine, and 15 mL of chloroform. The mixture was added dropwise and stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and a mixture of the obtained residue and chloroform (10 mL) was added dropwise with a mixture of ethylmethylamine (0.14 mL), triethylamine (0.31 mL), and chloroform (10 mL), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was filtered and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (hexane: ethyl acetate = 1: 1) to obtain 0.45 g of the present compound 11 shown below.

Compound 11 of the present invention:
¹ H-NMR (CDCl ₃ ) δ: 8.02 (2H, d), 7.56 (2H, d), 6.48 (1H, br s), 3.43 (2H, q), 3.03 (3H, s), 1.21 (3H, t)

本発明化合物１２：
¹H-NMR (CDCl₃) δ: 8.59 (1H, t), 7.92-7.89 (1H, m), 7.86-7.82 (1H, m), 7.48 (1H, br s), 2.42 (2H, t), 1.83-1.74 (2H, m), 1.02 (3H, t) Production Example 3-1
0.19 mL of butyryl chloride was added dropwise to a mixture of 150 mg of 4-amino-3-fluorobenzonitrile, 0.38 mL of triethylamine, and 10 mL of THF, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was filtered and concentrated under reduced pressure. To a mixture of the obtained residue and 10 mL of ethanol, 0.22 mL of 50% aqueous hydroxylamine solution was added dropwise and stirred at 80 ° C. for 2 hours. The reaction solution was concentrated under reduced pressure. To a mixture of the obtained residue and 10 mL of DMF, 0.22 mL of pyridine was added dropwise at room temperature, and subsequently 0.18 mL of trifluoroacetic anhydride was added dropwise, followed by stirring at 100 ° C. for 2 hours. Water was added to the reaction solution, the precipitate was filtered, and the filtrate was washed with water and hexane and dried under reduced pressure to obtain 130 mg of the present compound 12 shown below.

Compound 12 of the present invention:
¹ H-NMR (CDCl ₃ ) δ: 8.59 (1H, t), 7.92-7.89 (1H, m), 7.86-7.82 (1H, m), 7.48 (1H, br s), 2.42 (2H, t), 1.83-1.74 (2H, m), 1.02 (3H, t)

で示される化合物において、Ｘ、Ｒ³及びＲ⁴が下記で示される化合物。 Production Example 3-2
The compounds produced according to the method described in Production Example 3-1 and their physical property values are shown below.
Formula (3)

In which X, R ³ and R ⁴ are as follows:

Compound 13 of the present invention (X: CH (CH ₃ ) _2, R ³ : F, R ⁴ : H):
¹ H-NMR (CDCl ₃ ) δ: 8.60 (1H, t), 7.90-7.92 (1H, m), 7.83-7.86 (1H, m), 7.52 (1H, br s), 2.55-2.65 (1H, m ), 1.29 (6H, d)
Compound 14 of the present invention (X: CH ₂ CH ₂ CH ₃ , R ³ : H, R ⁴ : F):
¹ H-NMR (CDCl ₃ ) δ: 8.03 (1H, t), 7.79-7.83 (1H, m), 7.34 (1H, br s), 7.28-7.30 (1H, m), 2.39 (2H, t), 1.74-1.83 (2H, m), 1.03 (3H, t)
Compound 15 of the present invention (X: CH (CH ₃ ) _2, R ³ : H, R ⁴ : F):
¹ H-NMR (CDCl ₃ ) δ: 8.03 (1H, t), 7.81-7.84 (1H, m), 7.37 (1H, br s), 7.30-7.32 (1H, m), 2.50-2.60 (1H, m ), 1.29 (6H, d)

In the compounds of the present invention, a compound in which the combination of X, R ³ , R ⁴ , R ⁵ and R ^{6 is} the combination described in any of compound numbers A1 to A69 can be produced according to the above production method. it can. Among the compounds of the present invention, the compounds of Compound Nos. A1 to A69 are represented as the present compounds A1 to A69, and the present compounds A1 to A69 are collectively represented as the present compound A.

For example, the compound A4 of the present invention represents a compound represented by the following structure in which X, R ³ , R ⁴ , R ⁵ and R ⁶ are the combinations described in the compound number A4 in the compound of the present invention.

[Compound number; X, R ³ , R ⁴ , R ⁵ , R ⁶ ]: [A1; Pr, H, H, H, H], [A2; i-Pr, H, H, H, H], [ A3; Bu, H, H, H, H], [A4; CH ₃ CH ₂ (CH ₃ ) CH, H, H, H, H], [A5; (CH ₃ ) ₂ CHCH ₂ , H, H, H, H], [A6; (CH ₃ ) ₃ C, H, H, H, H], [A7; Pen, H, H, H, H], [A8; CH ₃ CH ₂ CH ₂ (CH ₃ ) CH, H, H, H, H], [A9; CH ₃ CH ₂ (CH ₃ ) CHCH ₂ , H, H, H, H], [A10; (CH ₃ ) ₂ CH ₂ CH ₂ , H, H, H, H], [A11; (CH ₃ ) ₂ CH (CH ₃ ) CH, H, H, H, H], [A12; CH ₃ CH ₂ (CH ₃ ) ₂ C, H, H, H , H], [A13; (CH ₃ ) ₃ CCH ₂ , H, H, H, H], [A14; (CH ₂ CH ₂ ) ₂ CH, H, H, H, H], [A15; Pr, F, H, H, H], [A16; i-Pr, F, H, H, H], [A17; Bu, F, H, H, H], [A18; CH ₃ CH ₂ (CH ₃ ) CH, F, H, H, H], [A19; (CH ₃ ) ₂ CHCH ₂ , F, H, H, H], [A20; (CH ₃ ) ₃ C, F, H, H, H], [A21; Pen, F, H, H, H], [A22; CH ₃ CH ₂ CH ₂ (CH ₃ ) CH, F, H, H, H], [A23; CH ₃ CH ₂ (CH ₃ ) CHCH ₂ , F, H, H, H], [A24; (CH ₃ ) ₂ CH ₂ CH ₂ , F, H, H, H], [A25; (CH ₃ ) ₂ CH (CH ₃ ) CH, F, H, H, H], [A26; CH ₃ CH ₂ (CH ₃ ) ₂ C, F, H, H, H], [A27; (CH ₃ ) ₃ CCH ₂ , F, H, H, H], [A28; (CH ₂ CH ₂ ) ₂ CH, F, H, H, H], [A29; Pr, H, F, H, H], [A30; i-Pr, H, F, H, H] , [A31; Bu, H, F, H, H], [A32; C H ₃ CH ₂ (CH ₃ ) CH, H, F, H, H], [A33; (CH ₃ ) ₂ CHCH ₂ , H, F, H, H], [A34; (CH ₃ ) ₃ C, H , F, H, H], [A35; Pen, H, F, H, H], [A36; CH ₃ CH ₂ CH ₂ (CH ₃ ) CH, H, F, H, H], [A37; CH ₃ CH ₂ (CH ₃ ) CHCH ₂ , H, F, H, H], [A38; (CH ₃ ) ₂ CH ₂ CH ₂ , H, F, H, H], [A39; (CH ₃ ) ₂ CH (CH ₃ ) CH, H, F, H, H], [A40; CH ₃ CH ₂ (CH ₃ ) ₂ C, H, F, H, H], [A41; (CH ₃ ) ₃ CCH ₂ , H , F, H, H], [A42; (CH ₂ CH ₂ ) ₂ CH, H, F, H, H], [A43; NMeEt, H, H, H, H], [A44; NMePr, H, H, H, H], [A45; NMe (i-Pr), H, H, H, H], [A46; NEt ₂ , H, H, H, H], [A47; NEtPr, H, H, H, H], [A48; NEt (i-Pr), H, H, H, H], [A49; NPr 2, H, H, H, H], [A50; NPr (i-Pr), H , H, H, H], [A51; N (i-Pr) ₂ , H, H, H, H], [A52; NMeEt, F, H, H, H], [A53; NMePr, F, H , H, H], [A54; NMe (i-Pr), F, H, H, H], [A55; NEt ₂ , F, H, H, H], [A56; NEtPr, F, H, H , H], [A57; NEt (i-Pr), F, H, H, H], [A58; NPr ₂ , F, H, H, H], [A59; NPr (i-Pr), F, H, H, H], [A60; N (i-Pr) ₂ , F, H, H, H], [A61; NMeEt, H, F, H, H], [A62; NMePr, H, F, H, H], [A63; NMe (i-Pr), H, F, H, H], [A64; NEt 2, H, F, H, H], [A65; nEtPr, H, F, H, H], [A66; NEt ( i-Pr), H, F, H, H], [A67; NPr 2, H, F, H, H], [A68; NPr (i-Pr), H, F , H, H], [A 69; N (i-Pr) ₂ , H, F, H, H]

The compound of the present invention can be used in combination or in combination with a bactericidal active ingredient, insecticidal active ingredient, acaricidal active ingredient, nematocidal active ingredient, plant growth regulating ingredient or synergist (hereinafter collectively referred to as this ingredient). it can. Below, the example of the combination of this invention compound and this component is described. For example, tebuconazole + SX means a combination of tebuconazole and SX. In addition, the abbreviation for SX means any one compound selected from the compounds A1 to A69 of the present invention. The numbers in parentheses represent CAS registration numbers.
Tebuconazole + SX, prothioconazole + SX, metconazole + SX, ipconazole + SX, triticonazole + SX, difenoconazole + SX, imazalil + SX triadimenol) + SX, tetraconazole + SX, flutriafol + SX, bromuconazole + SX, propiconazole + SX, mefentrifluconazole + SX, ipfentrifluconazole (SX) ipfentrifluconazole) + SX, epoxiconazole + SX, cyproconazole + SX, mandestrobin + SX, azoxystrobin + SX, pyraclostrobin + SX, trifloxystrobin ( trifloxystrobin) + SX, fluoxast Robin (fluoxastrobin) + SX, picoxystrobin (SX), fenamidone (fenamidone) + SX, dimoxystrobin (SX) + metominostrobin (SX), pyribencarb (SX), sedaxane (SX) Penflufen + SX, fluxapyroxad + SX, fluopyram + SX, benzovindiflupyr + SX, boscalid + SX, carboxin + SX, penthiopyrad + SX, flutolanil (flutolanil) + SX, bixafen + SX, pydiflumetofen + SX, 3-difluoromethyl-N- (7-fluoro-1,1,3-trimethylindan-4-yl) -1-methylpyrazole -4-carboxamide (1383809-87-7) + SX, N-cyclopropyl-3- (difluoromethyl) -5 Fluoro-N- (5-chloro-2-isopropylbenzyl) -1-methyl-1H-pyrazole-4-carboxamide (1255734-28-1) + SX, 3-difluoromethyl-1-methyl-N- (1,1 , 3-Trimethylindan-4-yl) pyrazole-4-carboxamide (141573-94-6) + SX, 3-difluoromethyl-1-methyl-N-[(3R) -1,1,3-trimethylindan-4 -Yl] pyrazole-4-carboxamide (1352994-67-2) + SX, metalaxyl + SX, metalaxyl-M + SX, metrafenone + SX, cyflufenamid + SX, proquinazid + SX, 3-chloro-5-phenyl-6-methyl-4- (2,6-difluorophenyl) pyridazine (1358061-55-8) + SX, 1- (2-{[1- (4-chlorophenyl) -1H-pi Zol-3-yl] oxymethyl} -3-methylphenyl) -4-methyl-1,4-dihydrotetrazol-5-one (1472649-01-6) + SX, 4- (2-bromo-4-fluorophenyl) ) -N- (2-chloro-6-fluorophenyl) -1,3-dimethyl-1H-pyrazol-5-amine (1362477-26-6) + SX, fenpicoxamid + SX, N '-( 2,5-dimethyl-4-phenoxyphenyl) -N-ethyl-N-methylmethanimidamide (1052688-31-9) + SX, isothianil + SX, oxolinic acid + SX, ferimzone + SX , Phthalide + SX, kasugamycin + SX, tebufloquin + SX, quinofumelin + SX, fenpyrazamine + SX, procymidone + SX, fludioxonil xonil + SX, tolclofos-methyl + SX, thiabendazole + SX, ethaboxam + SX, picarbutrazox + SX, oxathiapiprolin + SX, iminoctadine tritate + SX, iminoctadine albesilate + SX, fenpropimorph + SX, fenpropidin + SX, spiroxamine + SX, chlorothalonil + SX, folpet + SX, captan ( captan + SX, thiram + SX, silthiofam + SX, mancozeb + SX, cartap + SX, clothianidin + SX, thiamethoxam + SX, imidacloprid + SX, thiacloprid + SX, thiacloprid + SX + SX, flupyradifurone + SX, Sulfoxaflor + SX, triflumezopyrim + SX, dicloromezotiaz + SX, beta-cyfluthrin + SX, tefluthrin + SX, fipronil + SX, chlorantraniliprolol (chlorantraniliprole) + SX, cyantraniliprole + SX, tetraniliprole + SX, thiodicarb + SX, carbofuran + SX, fluxametamide + SX, afoxolaner + SX, uralflner + SX, broflanilide + SX, abamectin + SX, fluensulfone + SX, fluazaindolizine + SX, tioxazafen + SX, (E) -N- {1-[(6-chloro Pyridin-3-yl) methyl] pyridine-2 (1H) Iridene} -2,2,2-trifluoroacetamide (1689566-03-7) + SX, Mycorrhizal Fungi + SX, Bacillus firmus + SX, Bacillus amyloliquefaciens (Bacillus) amyloliquefaciens) + SX, Pasteuria nishizawae + SX, Pasteuria penetrans + SX.

  The mixing ratio of the compound of the present invention and this component is not particularly limited, but is 1000: 1 to 1: 1000, 500: 1 to 1: 500, 100: 100 by weight ratio (the compound of the present invention: this component). 1-1: 100, 50: 1 to 1:50, 20: 1 to 1:20, 10: 1 to 1:10, 3: 1 to 1: 3, 1: 1 to 1: 500, 1: 1 to 1: 100, 1: 1 to 1:50, 1: 1 to 1:20, 1: 1 to 1:10, and the like.

  By treating the compound of the present invention with a plant, improvement in seedling establishment rate, increase in the number of healthy leaves, increase in plant height, increase in plant weight, increase in leaf area, increase in the number or weight of seeds or fruits, number of flowers or number of fruits The effect of promoting the growth of the plant, such as an increase in plant weight and an increase in root growth, is obtained. In addition, by treating the compound of the present invention with a plant, tolerance to temperature stress such as high temperature stress or low temperature stress, moisture stress such as drought stress or excessive humidity stress, or abiotic stress such as salt stress is improved.

  Next, formulation examples are shown.

Formulation Example 1 A formulation is obtained by thoroughly pulverizing and mixing 50 parts of any one of the compounds A 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 After mixing 20 parts of any one of the compounds A of the present invention and 1.5 parts of sorbitan trioleate with 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol, and finely pulverizing by a wet pulverization method, Into this, 40 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added, and further 10 parts of propylene glycol is added and stirred to obtain a preparation.

Formulation Example 3 A formulation is obtained by thoroughly pulverizing and mixing 2 parts of any one of the compounds A of the present invention, 88 parts of kaolin clay and 10 parts of talc.

Formulation Example 4 A formulation is obtained by thoroughly mixing 5 parts of any one compound of the present compound A, 14 parts of polyoxyethylene styryl phenyl 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 A 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, add water and knead well The preparation is obtained by combining and granulating and drying.

Formulation Example 6 A mixture of 35 parts of a mixture of polyoxyethylene alkyl ether sulfate ammonium salt and white carbon (weight ratio 1: 1), 20 parts of any one of the compounds A of the present invention, and 45 parts of water were thoroughly mixed. A formulation is obtained.

  Next, test examples show that the compounds of the present invention are useful for controlling plant diseases.

Test Example 1 Control Trial against Wheat Leaf Blight Fungus (Septoria tritici) The present compound 1, 2, 3, 5, 7, 8, 11 or 12 was diluted with dimethyl sulfoxide so as to contain 1500 ppm, and titer plate (96 well) After 1 μL was dispensed, 150 μL of a potato broth liquid medium (PDB medium) inoculated with spores of wheat leaf blight was previously dispensed. This plate was cultured at 18 ° C. for 5 days to grow wheat leaf blight fungi. Then, the absorbance at 550 nm of each well of the titer plate was measured, and the value was taken as the growth degree of wheat leaf blight fungi. As a result, the growth degree in the group treated with the present compound 1, 2, 3, 5, 7, 8, 11 or 12 was 50% or less of the growth degree in the untreated group.

Test Example 2 Control test against tomato leaf mold (Cladosporium fulvum) The present compound 1, 2, 3, 4, 5, 6, 7, 8 or 12 was diluted with dimethyl sulfoxide so as to contain 1500 ppm, and titer plate (96 QoI resistant strain in which the base sequence was mutated so that the 129th amino acid residue of cytochrome b was substituted from phenylalanine to leucine among the genes encoding tomato leaf blight fungus (cytochrome b encoding gene) 150 μL of the potato broth liquid medium (PDB medium) inoculated with the spores of This plate was cultured at 18 ° C. for 5 days to proliferate the tomato leaf mold, and then the absorbance at 550 nm of each well of the titer plate was measured, and the value was taken as the growth degree of the tomato leaf mold. As a result, the growth degree in the group treated with the present compound 1, 2, 3, 4, 5, 6, 7, 8 or 12 was 50% or less of the growth degree in the untreated group.

Test Example 3 Control test against soybean anthracnose (Colletotrichum truncatum) Diluted with dimethyl sulfoxide so that the compound 7 of the present invention contains 1500 ppm, dispensed 1 μL into a titer plate (96-well), and inoculated with spores of soybean anthracnose fungus in advance. 150 μL of the prepared potato broth liquid medium (PDB medium) was dispensed. This plate was cultured at 18 ° C. for 4 days to propagate soybean anthracnose fungi, and then the absorbance at 550 nm of each well of the titer plate was measured, and the value was taken as the degree of growth of soybean anthracnose fungus. As a result, the degree of growth in the group treated with Compound 7 of the present invention was 50% or less of the degree of growth in the untreated group.

Test Example 4 Control test against wheat rust (Puccinia recondita) A plastic pot was stuffed with soil, sowed with wheat (cultivar: Shirogane), and cultivated in a greenhouse for 9 days. The compound 1, 2, 4, 5, 8 or 11 of the present invention formulated according to the method described in Formulation Example 6 is prepared with water so that the concentration is 500 ppm, and the prepared solution is prepared from the above wheat leaf. The foliage was sprayed so as to adhere well to the surface. After spraying, the wheat was air-dried and cultivated under light at 20 ° C. for 5 days, and then sprinkled with spores of wheat rust fungus. After inoculation, the wheat was placed in a dark and humid environment at 23 ° C. for 1 day, and then cultivated at 20 ° C. for 8 days under illumination. As a result, the lesion area in the wheat treated with the present compound 1, 2, 4, 5, 8 or 11 was 30% or less of the lesion area in the untreated wheat.

Test Example 5 Control test against wheat rust (Puccinia recondita) A plastic pot was stuffed with soil, sowed with wheat (cultivar: Shirogane), and cultivated in a greenhouse for 9 days. The compound 1, 2, 3, 4, 5, 8 or 11 of the present invention formulated according to the method described in Formulation Example 6 is prepared with water to a concentration of 200 ppm, and the prepared solution is prepared from the above wheat. The foliage was sprayed so as to adhere well to the leaf surface. After spraying, the wheat was air-dried and cultivated under light at 20 ° C. for 5 days, and then sprinkled with spores of wheat rust fungus. After inoculation, the wheat was placed in a dark and humid environment at 23 ° C. for 1 day, and then cultivated at 20 ° C. for 8 days under illumination. As a result, the lesion area in the wheat treated with the compound 1, 2, 3, 4, 5, 8 or 11 of the present invention was 30% or less of the lesion area in the untreated wheat.

Test Example 6 Control Trial for Wheat Leaf Blight (Septoria tritici) A plastic pot was filled with soil, and wheat (cultivar; Apoge) was sown therein and cultivated in a greenhouse for 10 days. The compound 1, 2, 8, or 11 of the present invention formulated according to the method described in Formulation Example 6 is prepared with water so that the concentration is 500 ppm, and the prepared solution is sufficiently adhered to the leaf surface of the wheat. The foliage was sprayed like so. After spraying, the wheat was air-dried, and after 4 days, an aqueous suspension of wheat leaf blight spores was spray-inoculated. After inoculation, the wheat was placed under high humidity at 18 ° C. for 3 days, then placed under illumination for 14 to 18 days, and then the lesion area was examined. As a result, the lesion area in the wheat treated with the present compound 1, 2, 8, or 11 was 30% or less of the lesion area in the untreated wheat.

Test Example 7 Control test against wheat leaf blight (Septoria tritici) A plastic pot was filled with soil, and wheat (cultivar; Apoge) was sown therein and cultivated in a greenhouse for 10 days. The compound 1, 2, or 11 of the present invention formulated according to the method described in Formulation Example 6 is prepared with water so as to have a concentration of 200 ppm, and the prepared solution is sufficiently adhered to the leaf surface of the wheat. The foliage was sprayed on the ground. After spraying, the wheat was air-dried, and after 4 days, an aqueous suspension of wheat leaf blight spores was spray-inoculated. After inoculation, the wheat was placed under high humidity at 18 ° C. for 3 days, then placed under illumination for 14 to 18 days, and then the lesion area was examined. As a result, the lesion area in the wheat treated with the present compound 1, 2, or 11 was 30% or less of the lesion area in the untreated wheat.

Test Example 8 Control test against barley cloud disease (Rhynchosporium secalis) A plastic pot was filled with soil, and barley (cultivar: Nishinohoshi) was sown therein and cultivated in a greenhouse for 7 days. The compound 11 of the present invention formulated according to the method described in Formulation Example 6 was prepared with water to a concentration of 200 ppm, and the prepared solution was sprayed on the foliage so as to adhere well to the leaf surface of the barley. . After spraying, the barley was air-dried, and one day later, an aqueous suspension of barley cloud fungus spores was spray-inoculated. After inoculation, the barley was placed under humid conditions at 15 ° C. for 3 days, and then cultivated in a greenhouse for 14 days. As a result, the lesion area in the barley treated with Compound 11 of the present invention was 30% or less of the lesion area in the untreated barley.

Test Example 9 Pyrephorophora teres control test A plastic pot was filled with soil, and barley (cultivar: Nishinohoshi) was sown therein and cultivated in a greenhouse for 7 days. The compound 5 of the present invention formulated in accordance with the method described in Formulation Example 6 is prepared with water so that the concentration is 500 ppm, and the prepared solution is sprayed on the foliage so that it adheres sufficiently to the leaf surface of the barley. did. After spraying, the barley was air-dried, and two days later, a water suspension of barley reticular fungus spores was spray-inoculated. After inoculation, the barley was placed under high humidity in a greenhouse at 23 ° C. during the daytime and 20 ° C. during the night for 3 days and then cultivated in the greenhouse for 7 days. As a result, the lesion area in the barley treated with Compound 5 of the present invention was 30% or less of the lesion area in the untreated barley.

Test Example 10 Control test against soybean rust (Phakopsora pachyrhizi) A plastic pot was filled with soil, and then soybean (cultivar; Kurosengoku) was sown, cultivated in a greenhouse for 10 days, and an aqueous suspension of soybean rust fungus spores. Was spray-inoculated. After inoculation, the present compound 1 was formulated according to the method described in Formulation Example 6 after placing soybeans in a humid room at 23 ° C. in the daytime and 20 ° C. for 1 day in a humid room and then cultivating in the greenhouse for 2 days. 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, or 13 is prepared with water so that the concentration becomes 200 ppm, and the prepared solution is sufficiently adhered to the leaf surface of the soybean. The foliage was sprayed like so. After spraying, the soybeans were air-dried and cultivated in a greenhouse for 8 days, and then the lesion area was examined. As a result, the lesion areas in soybeans treated with the compounds 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12 or 13 of the present invention are all lesion spots in untreated soybeans. It was 30% or less of the area.

Test Example 11 Control Test against Soybean Rust (Phakopsora pachyrhizi) A plastic pot was filled with soil, and then soybean (cultivar; Kurosengoku) was sown therein and cultivated in a greenhouse for 13 days. The compound 1, 2, 3, 4, 5, 8 or 11 of the present invention formulated according to the method described in Formulation Example 6 is prepared with water so as to have a concentration of 200 ppm. The foliage was sprayed so as to adhere well to the leaf surface. After spraying, the soybeans were air-dried, and after 4 days, sprayed with a water suspension of soybean rust spores. After inoculation, the soybeans were placed in a humid room at 23 ° C. in the daytime and 20 ° C. for one day under high humidity, then cultivated in the greenhouse for 10 days, and then the lesion area was examined. As a result, the lesion area in soybean treated with the present compound 1, 2, 3, 4, 5, 8 or 11 was 30% or less of the lesion area in untreated soybean.

Test Example 12 Control test against rice blast (Magnaporthe grisea) A plastic pot was filled with soil, rice (cultivar: Hinohikari) was sown there, and cultivated in a greenhouse for 20 days. Thereafter, the present compound 1, 2 or 8 formulated according to the method described in Formulation Example 6 is prepared with water so that the concentration is 500 ppm, and the prepared solution is sufficiently adhered to the rice leaf surface. The foliage was sprayed like so. After spraying, the rice is air-dried and left for 6 days in contact with a rice seedling (variety: Hinohikari) that has been treated with the rice blast fungus under a high humidity of 24 ° C in the daytime and 20 ° C in the nighttime. The lesion area was investigated. As a result, the lesion area in the rice treated with the present compound 1, 2, or 8 was 30% or less of the lesion area in the untreated rice.

Test Example 13 Control test against rice blast (Magnaporthe grisea) A plastic pot was filled with soil, rice (cultivar: Hinohikari) was sown therein, and cultivated in a greenhouse for 20 days. Thereafter, the compound 8 of the present invention formulated according to the method described in Formulation Example 6 is prepared with water so that the concentration becomes 200 ppm, and the prepared solution is stalks and leaves so as to adhere well to the leaf surface of rice. Scattered. After spraying, the rice is air-dried and left for 6 days in contact with a rice seedling (variety: Hinohikari) that has been treated with the rice blast fungus under a high humidity of 24 ° C in the daytime and 20 ° C in the nighttime. The lesion area was investigated. As a result, the lesion area in rice treated with Compound 8 of the present invention was 30% or less of the lesion area in untreated rice.

  Next, reference compounds show that the compounds of the present invention are useful for controlling harmful arthropods.

Reference test example 1
Compound 11 of the present invention formulated according to the method described in Formulation Example 6 was prepared with water so that the concentration was 500 ppm, and the prepared solution was added to cabbage seedlings (second to third true leaves) planted in a container. The stems and leaves were sprayed so as to adhere well to the leaf surface during the development stage. After spraying, the cabbage was air-dried, and the stems and leaves of this seedling were cut out and placed in a container with filter paper. To this, five 5th instar larvae were released. After 5 days, the number of live insects was counted, and the death rate was calculated from the following formula.
Death rate% = (1−Number of surviving insects / 5) × 100
As a result, the cabbage treated with the compound 11 of the present invention showed a death rate of 80% or more.

Comparative Test Example A plastic pot was filled with soil, soybean (variety: Kurosengoku) was sown there, and cultivated in a greenhouse for 13 days. Compound 1 or 11 of the present invention formulated according to the method described in Formulation Example 6 or Compound 3.2 (N, N-dimethyl-N′-4- [described in JP-A-63-162680) 5- (trifluoromethyl) -1,2,4-oxadiazol-3-yl] phenylurea) or compound 3.14 (N-4- [5- (trifluoromethyl) -1,2,4- [Oxadiazol-3-yl] phenylpropionamide) was prepared with water so that the concentration became 12.5 ppm, and the prepared solution was sprayed on the foliage so that it sufficiently adhered to the leaves of the soybean. After spraying, the soybeans were air-dried, and after 4 days, sprayed with a water suspension containing spores of soybean rust fungus (Phakopsora pachyrhizi). After inoculation, the soybeans were placed in a humid room at 23 ° C. in the daytime and 20 ° C. for one day under high humidity, then cultivated in the greenhouse for 10 days, and then the lesion area was examined. As a result, as shown in Table A, under the same conditions, the lesion area in the soybean treated with the compound 1 or 11 of the present invention is 10% or less of the lesion area in the untreated soybean. The lesion area in soybean treated with Compound 3.2 or Compound 3.14 described in Japanese Utility Model Publication No. 63-162680 was 76% or more of the lesion area in untreated soybean.
[Table A]

  The compound of the present invention has a controlling effect against plant diseases and is useful as an active ingredient of a plant disease controlling agent.

Claims (5)

Formula (1)

[Where,
X represents a C3-C5 alkyl group, or NR ¹ R ² ;
R ¹ represents a C1-C3 alkyl group,
R ² represents a C2-C3 alkyl group,
R ³ , R ⁴ , R ⁵ and R ⁶ each independently represent a hydrogen atom or a fluorine atom. ]
A compound represented by The compound of Claim 1 whose R < ³ >, R < ⁴ >, R < ⁵ > and R < ⁶ > are hydrogen atoms. The plant disease control agent containing the compound of Claim 1 or Claim 2. A method for controlling plant diseases by treating a plant or soil with an effective amount of the compound according to claim 1 or 2. Use of the compound according to claim 1 or claim 2 for controlling plant diseases.