WO2018047670A1 - イミド化合物及びその用途 - Google Patents
イミド化合物及びその用途 Download PDFInfo
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- WO2018047670A1 WO2018047670A1 PCT/JP2017/030861 JP2017030861W WO2018047670A1 WO 2018047670 A1 WO2018047670 A1 WO 2018047670A1 JP 2017030861 W JP2017030861 W JP 2017030861W WO 2018047670 A1 WO2018047670 A1 WO 2018047670A1
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- Prior art keywords
- compound
- disease
- present
- plant
- imide compound
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- 0 CC(CC(C)(C)c1c(*)cc2)c1c2N(C(c1c[n](C)nc1C(F)F)=O)C(c1c[n](C)nc1C(F)F)=O Chemical compound CC(CC(C)(C)c1c(*)cc2)c1c2N(C(c1c[n](C)nc1C(F)F)=O)C(c1c[n](C)nc1C(F)F)=O 0.000 description 1
- ZDKWZKNQRDPUHH-UHFFFAOYSA-N CC(CC(C)(C)c1c(cc2)F)c1c2N(C(c1c[n](C)nc1C(F)F)=O)C(c1c[n](C)nc1C(F)F)=O Chemical compound CC(CC(C)(C)c1c(cc2)F)c1c2N(C(c1c[n](C)nc1C(F)F)=O)C(c1c[n](C)nc1C(F)F)=O ZDKWZKNQRDPUHH-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
Definitions
- the present invention relates to an imide compound and its use.
- Patent Document 1 Conventionally, various compounds have been developed to control plant diseases (see Patent Document 1).
- An object of the present invention is to provide a compound having an excellent control effect against plant diseases.
- the present inventors have found that the imide compound represented by the following formula (I) has an excellent control effect against plant diseases. It was. That is, the present invention is as follows. [1] Formula (I) [Wherein, R represents a fluorine atom or a hydrogen atom. ] An imide compound represented by the following (hereinafter referred to as the present compound). [2] The imide compound represented by the formula (I) is represented by the formula (II) [Wherein, R represents a fluorine atom or a hydrogen atom. ] The imide compound according to [1], which is an imide compound represented by formula (hereinafter referred to as compound (II)).
- a plant disease control agent containing the imide compound according to [1] or [2] and an inert carrier (hereinafter referred to as the present invention control agent).
- Formula (I) [Wherein, R represents a fluorine atom or a hydrogen atom.
- composition containing one or more selected from the group consisting of an insecticidal active ingredient, an acaricidal active ingredient, a nematicidal active ingredient, a plant growth regulator, a synergist and other plant disease control ingredients .
- plant diseases can be controlled.
- Examples of the compound of the present invention include the following compounds.
- a compound wherein R is a fluorine atom;
- a compound wherein R is a hydrogen atom;
- a compound wherein R is a fluorine atom;
- compounds wherein R is a hydrogen atom;
- Compound (II) and formula (III) A compound having a ratio of 1/1 to 100000/1 with an imide compound represented by formula (hereinafter referred to as compound (III)), wherein R is a fluorine atom in compound (II), and R in compound (III) A compound having a ratio of 1/1 to 100,000 / 1 with a compound that is a fluorine atom; A compound in which the ratio of the compound in which R is a hydrogen atom in compound (II) to the compound in which R is a fluorine atom in compound (III) is 1/1 to 100,000 / 1;
- the present control agent contains the present compound and an inert carrier.
- the control agent of the present invention is usually prepared by mixing the compound of the present invention with an inert carrier such as a solid carrier or a liquid carrier, oil, and / or a surfactant, and if necessary, a fixing agent, a dispersant, a stabilizer, etc.
- These preparations contain the compound of the present invention in a weight ratio of usually 0.1 to 99%, preferably 0.2 to 90%.
- Examples of the solid support include clays (for example, kaolin clay, 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). , Calcium carbonate) and the like.
- Examples of the liquid carrier include water, alcohols (methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, phenoxyethanol, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, etc.), and aromatic carbonization.
- Hydrogen toluene, xylene, ethylbenzene, dodecylbenzene, phenylxylylethane, methylnaphthalene, etc.
- aliphatic hydrocarbons hexane, cyclohexane, kerosene, light oil, etc.
- esters ethyl acetate, butyl acetate, isopropyl myristate
- Ethyl oleate diisopropyl adipate, diisobutyl adipate, propylene glycol monomethyl ether acetate, etc.
- nitriles ethers (diisopropyl Ether, 1,4-dioxane, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, 3-methoxy-3-methyl-1-butanol
- surfactant examples include alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, alkyl aryl ethers and polyoxyethylene compounds thereof, polyoxyethylene glycol ethers, polyhydric alcohol esters, sugar alcohol derivatives. Is mentioned.
- formulation adjuvants include, for example, fixing agents, dispersants, and stabilizers.
- 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, BHA (2-tert-butyl-4 A mixture of -methoxyphenol and 3-tert-butyl-4-methoxyphenol), vegetable oils, mineral oils and fatty acids.
- polysaccharides eg, starch, arabic gum, cellulose derivatives, alginic acid
- lignin derivatives bentonite
- Sugars synthetic water-soluble polymers (eg, polyvinyl alcohol, polyvinyl pyrrolidone, polyacrylic acids), isoprop
- Oils and surfactants that can be used in combination with the compounds of the present invention include Nimbus (registered trademark), Assist (registered trademark), Aureo (registered trademark), Iharol (registered trademark), and 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), EnSpra N (R), BANOLE (registered trademark).
- the compound of the present invention is applied as the control agent of the present invention.
- the method is not particularly limited as long as the present control agent can be applied.
- treatment to plant bodies such as foliage spraying, soil treatment, etc.
- the treatment to the planting place of a plant the treatment to seeds, such as seed disinfection, are mentioned.
- the treatment amount of the compound of the present invention depends on the type of plant to be treated, the type and occurrence frequency of plant diseases to be controlled, formulation form, treatment time, treatment method, treatment place, weather conditions, etc.
- the compound of the present invention is usually 1 to 500 g per 1000 m 2 when it is treated on the foliage of the plant or on the soil where the plant is grown.
- Emulsions, wettable powders, flowables and the like are usually treated by diluting with water and spraying.
- 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.
- 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 such as cultivated land in cultivated lands where the following plants are cultivated.
- Agricultural crops corn, rice, wheat, barley, rye, oats, sorghum, cotton, soybeans, peanuts, buckwheat, sugar beet, rapeseed, sunflower, sugarcane, tobacco, vegetables, solanaceous vegetables (eggplants, tomatoes, peppers, peppers, potatoes) Cucumber, pumpkin, zucchini, watermelon, melon, etc., cruciferous vegetables (radish, turnip, horseradish, coral rabi, 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) ), Strawberry, sweet potato, yam, taro, etc., flowers, foliage plants, Fruit trees;
- 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.
- 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
- Rice 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.
- the obtained organic layer was washed successively with water, saturated aqueous sodium hydrogen carbonate and water, dried over magnesium sulfate, and concentrated under reduced pressure.
- the obtained residue was subjected to silica gel column chromatography to obtain the compound described below (hereinafter referred to as the present compound (1)) (optical purity 99.9%).
- Production Example 2 In accordance with the method described in Production Example 1, using 7-fluoro-1,1,3-trimethyl-4-aminoindane instead of (R) -1,1,3-trimethyl-4-aminoindane, This invention compound (2) shown by these was obtained.
- the compound of the present invention and at least one selected from the group consisting of insecticidal active ingredients, acaricidal active ingredients, nematocidal active ingredients, plant growth regulating ingredients, synergists and other plant disease controlling ingredients (hereinafter collectively referred to as this ingredient) can be controlled by treating the plant or the soil with a composition containing the toxic pests, harmful pests, phytopathogenic fungi and the like. Moreover, this invention compound and this component can be applied separately and a pest can be controlled. Examples of the insecticidal active ingredient, acaricidal active ingredient and nematocidal active ingredient include those prescribed by IRAC (Insecticide Resistance Action Committee).
- the plant growth regulating component means a component that controls plant growth, such as fruit set promotion and rooting promotion, and examples thereof include indole butyric acid.
- a synergist is one that enhances its efficacy when used in combination with other drugs, such as piperonyl butoxide.
- plant disease control components include bactericidal active components, which are components used to protect plants from diseases caused by phytopathogenic fungi (filamentous fungi and bacteria). For example, FRAC (Fungicide Resistance Action Committee : Antibacterial-resistant bacteria countermeasure committee) and the like.
- tebuconazole + SX means a combination of tebuconazole and SX.
- the abbreviation SX means any one compound selected from the compounds of the present invention.
- the numbers in parentheses represent CAS registration numbers.
- the ratio of the compound of the present invention to this component is not particularly limited, but the weight ratio (the compound of the present invention: this component) is, for example, 1000: 1 to 1: 1000, 500: 1 to 1: 500, 100: 1 to 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.
- Formulation Example 1 A preparation is obtained by thoroughly pulverizing and mixing 50 parts of any one of the compounds 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 compound of the present invention and 1.5 parts of sorbitan trioleate were mixed with 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol and finely pulverized by a wet pulverization method. Thereafter, 40 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate is added to this, and 10 parts of propylene glycol is further added and stirred to obtain a preparation.
- Formulation Example 3 A formulation is obtained by thoroughly pulverizing and mixing 2 parts of any one compound of the present invention, 88 parts of kaolin clay and 10 parts of talc.
- Formulation Example 4 A preparation is obtained by thoroughly mixing 5 parts of any one of the compounds of the present invention, 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 of the present invention, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay, water is added and kneaded and granulated. The preparation is obtained by drying.
- Formulation Example 6 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 of the present invention and 45 parts of water are sufficiently mixed to obtain a preparation.
- Test example 1 A plastic pot was filled with soil, and wheat (variety: Shirogane) was sown therein and allowed to grow in a greenhouse for 9 days.
- the compound of the present invention (1), the compound of the present invention (2) or the compound of the present invention (3) formulated according to the method described in Formulation Example 6 is mixed with water to a concentration of 500 ppm, and the mixture is mixed. Then, the stems and leaves were sprayed so as to adhere well to the leaves of the wheat. After spraying, the wheat was air-dried and cultivated at 20 ° C. under illumination for 5 days, and then sprinkled with spores of wheat red rust fungus (Puccinia recondita).
- 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.
- the lesion area in the wheat treated with the present compound (1), the present compound (2) or the present compound (3) was 10% or less of the lesion area in the untreated wheat. .
- Test example 2 A plastic pot was filled with soil, and barley (variety: Nishinohoshi) was sown therein and grown in a greenhouse for 7 days.
- the compound of the present invention (2) or the compound of the present invention (3) formulated according to the method described in Formulation Example 6 is mixed with water so that the concentration becomes 500 ppm, and the mixture is added to the leaf surface of the barley.
- the foliage was sprayed so as to adhere well. After spraying, the barley was air-dried, and two days later, an aqueous suspension of barley reticulum spore spores was spray-inoculated. After inoculation, the barley was placed in a 23 ° C. daytime and 20 ° C.
- the lesion area in the barley treated with the present compound (2) or the present compound (3) was 10% or less of the lesion area in the untreated barley.
- 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.
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Abstract
Description
すなわち、本発明は以下のとおりである。
〔1〕 式(I)
〔式中、Rは、フッ素原子又は水素原子を表す。〕
で示されるイミド化合物(以下、本発明化合物と記す)。
〔2〕 式(I)で示されるイミド化合物が式(II)
〔式中、Rは、フッ素原子又は水素原子を表す。〕
で示されるイミド化合物(以下、化合物(II)と記す)である、〔1〕に記載のイミド化合物。
〔3〕 〔1〕又は〔2〕に記載のイミド化合物と、不活性担体とを含有する植物病害防除剤(以下、本発明防除剤と記す)。
〔4〕 〔1〕又は〔2〕に記載のイミド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〕に記載のイミド化合物の使用。
〔6〕 式(I)
〔式中、Rは、フッ素原子又は水素原子を表す。〕
で示されるイミド化合物、並びに殺虫活性成分、殺ダニ活性成分、殺センチュウ活性成分、植物成長調節成分、共力剤及び他の植物病害防除成分からなる群より選ばれる1種以上を含有する組成物。
本発明化合物において、Rがフッ素原子である化合物;
本発明化合物において、Rが水素原子である化合物;
化合物(II)において、Rがフッ素原子である化合物;
化合物(II)において、Rが水素原子である化合物;
で示されるイミド化合物(以下、化合物(III)と記す)との比が1/1~100000/1である化合物
化合物(II)においてRがフッ素原子である化合物と、化合物(III)においてRがフッ素原子である化合物との比が1/1~100000/1である化合物;
化合物(II)においてRが水素原子である化合物と、化合物(III)においてRがフッ素原子である化合物との比が1/1~100000/1である化合物;
化合物(II)においてRがフッ素原子である化合物と、化合物(III)においてRがフッ素原子である化合物との比が4/1~100000/1である化合物;
化合物(II)においてRが水素原子である化合物と、化合物(III)においてRが水素原子である化合物との比が4/1~100000/1である化合物;
液体担体としては、例えば、水、アルコール類(メタノール、エタノール、イソプロピルアルコール、ブタノール、ヘキサノール、ベンジルアルコール、エチレングリコール、プロピレングリコール、フェノキシエタノール等)、ケトン類(アセトン、メチルエチルケトン、シクロヘキサノン等)、芳香族炭化水素類(トルエン、キシレン、エチルベンゼン、ドデシルベンゼン、フェニルキシリルエタン、メチルナフタレン等)、脂肪族炭化水素類(ヘキサン、シクロヘキサン、灯油、軽油等)、エステル類(酢酸エチル、酢酸ブチル、ミリスチン酸イソプロピル、オレイン酸エチル、アジピン酸ジイソプロピル、アジピン酸ジイソブチル、プロピレングリコールモノメチルエーテルアセテート等)、ニトリル類、エーテル類(ジイソプロピルエーテル、1,4-ジオキサン、エチレングリコールジメチルエーテル、ジエチレングリコールジメチルエーテル、ジエチレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテル、ジプロピレングリコールモノメチルエーテル、3-メトキシ-3-メチル-1-ブタノール等)、アミド類、及びスルホキシド類が挙げられる。が挙げられる。
本発明の防除方法における、本発明化合物の処理量は、処理する植物の種類、防除対象である植物病害の種類や発生頻度、製剤形態、処理時期、処理方法、処理場所、気象条件等によっても異なるが、植物の茎葉に処理する場合又は植物を栽培する土壌に処理する場合は、本発明化合物は、1000m2あたり、通常1~500gである。
乳剤、水和剤、フロアブル剤等は通常水で希釈して散布することにより処理する。この場合、本発明化合物の濃度は、通常0.0005~2重量%である。粉剤、粒剤等は通常希釈することなくそのまま処理する。
果樹;仁果類(リンゴ、セイヨウナシ、ニホンナシ、カリン、マルメロ等)、核果類(モモ、スモモ、ネクタリン、ウメ、オウトウ、アンズ、プルーン等)、カンキツ類(ウンシュウミカン、オレンジ、レモン、ライム、グレープフルーツ等)、堅果類(クリ、クルミ、ハシバミ、アーモンド、ピスタチオ、カシューナッツ、マカダミアナッツ等)、液果類(ブルーベリー、クランベリー、ブラックベリー、ラズベリー等)、ブドウ、カキ、オリーブ、ビワ、バナナ、コーヒー、ナツメヤシ、ココヤシ等、
果樹以外の樹;チャ、クワ、花木、街路樹(トネリコ、カバノキ、ハナミズキ、ユーカリ、イチョウ、ライラック、カエデ、カシ、ポプラ、ハナズオウ、フウ、プラタナス、ケヤキ、クロベ、モミノキ、ツガ、ネズ、マツ、トウヒ、イチイ)等。
Aspergillus属、Penicillium属、Fusarium属、Gibberella属、Tricoderma属、Thielaviopsis属、Rhizopus属、Mucor属、Corticium属、Phoma属、Rhizoctonia属、及びDiplodia属菌等によって引き起こされる、各種作物の種子病害又は生育初期の病害。
Polymyxa属又はOlpidium属等によって媒介される各種作物のウイルス病。
イネの苗立枯細菌病(Burkholderia plantarii);キュウリの斑点細菌病(Pseudomonas syringae pv. Lachrymans);ナスの青枯病(Ralstonia solanacearum)、カンキツのかいよう病(Xanthomonas citri);ハクサイの軟腐病(Erwinia carotovora)等。
まず、本発明化合物の製造について、製造例を示す。
(R)-1,1,3-トリメチル-4-アミノインダン0.20g(光学純度96%)、ジイソプロピルエチルアミン1.2mL、4-ジメチルアミノピリジン0.02g、テトラエチレングリコールジメチルエーテル5mL、及び1-メチル-3-ジフルオロメチルピラゾール-4-カルボン酸クロライド0.46gを混合し、80℃で1時間撹拌し、ついで120℃で5時間撹拌した。反応混合物を室温まで冷却した後、得られた混合物に水、トルエン及び5%塩酸を加えて分液した。得られた有機層を水、飽和重曹水及び水で順次洗浄後、硫酸マグネシウムで乾燥し減圧下濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィーに付して下記に記載の化合物(以下、本発明化合物(1)と記す。)(光学純度99.9%)を得た。
本発明化合物(1)
1H-NMR (CDCl3) δ: 7.51 (1H, s),7.32 (1H, dd, J = 7.2Hz, 7.8Hz),7.22 (1H, d, J = 7.2Hz),7.13 (1H, t, J = 54Hz),7.07 (1H, d, J = 7.8Hz),6.96 (1H, t, J = 54Hz), 6.52 (1H, s), 3.89 (3H, s), 3.72 (3H, s),2.91-2.83 (1H, m),2.05 (1H, dd, J = 4.8Hz,7.8Hz), 1.57 (1H, dd, J = 7.8Hz、12.6Hz), 1.36 (3H, s), 1.24 (3H, d, J = 13.8 Hz),0.98 (3H, s).
[α]D 22=+113.5°(CHCl3,c1.1)
(R)-1,1,3-トリメチル-4-アミノインダンに代えて7-フルオロ-1,1,3-トリメチル-4-アミノインダンを用い、製造例1に記載の方法に準じて、下記で示される本発明化合物(2)を得た。
本発明化合物(2)
1H-NMR (CDCl3) δ: 7.53 (1H, s), 7.10 (1H, t, J = 53.8 Hz), 7.06 (1H, dd, J = 8.8, 4.4 Hz), 6.98 (1H, t, J = 8.8 Hz), 6.93 (1H, t, J = 54.5 Hz), 6.71 (1H, s), 3.91 (3H, s), 3.78 (3H, s), 2.97-2.88 (1H, m), 2.07 (1H, dd, J = 12.9, 8.1 Hz), 1.62 (1H, dd, J = 12.9, 8.1 Hz), 1.58 (3H, s), 1.48 (3H, s), 1.24 (3H, d, J = 6.9 Hz).
(R)-1,1,3-トリメチル-4-アミノインダンに代えて1,1,3-トリメチル-4-アミノインダンを用い、製造例1に記載の方法に準じて、下記で示される本発明化合物(3)を得た。
本発明化合物(3)
1H-NMR (CDCl3) δ: 7.51 (1H, s), 7.33 (1H, t, J = 7.6 Hz), 7.22 (1H, dd, J = 7.6, 1.0 Hz), 7.13 (1H, t, J = 53.5 Hz), 7.07 (1H, dd, J = 7.8, 1.0 Hz), 6.95 (1H, t, J = 54.8 Hz), 6.52 (1H, s), 3.91 (3H, s), 3.72 (3H, s), 2.92-2.83 (1H, m), 2.06 (1H, dd, J = 12.7, 7.7 Hz), 1.57 (1H, dd, J = 12.7, 7.5 Hz), 1.36 (3H, s), 1.24 (3H, d, J = 6.8 Hz), 0.99 (3H, s).
殺虫活性成分、殺ダニ活性成分及び殺センチュウ活性成分としてはIRAC(Insecticide Resistance Action Committee:殺虫剤抵抗性対策委員会)等で規定されるものが挙げられる。
植物成長調節成分とは、着果促進、発根促進のように、植物の成長をコントロールする成分を意味し、例えばインドール酪酸が挙げられる。
共力剤とは、他の薬剤と混合して用いた場合に、その効力を増強するものであり、例えばピペロニル ブトキサイドが挙げられる。
植物病害防除成分としては殺菌活性成分が挙げられ、殺菌活性成分とは、植物病原菌(糸状菌や細菌)に由来する病害から植物を守るために使用する成分であり、例えばFRAC(Fungicide Resistance Action Committee:殺菌剤耐性菌対策委員会)等で規定されるものが挙げられる。
テブコナゾール(tebuconazole)+SX、プロチオコナゾール(prothioconazole)+SX、メトコナゾール(metconazole)+SX、イプコナゾール(ipconazole)+SX、トリチコナゾール(triticonazole)+SX、ジフェノコナゾール(difenoconazole)+SX、イマザリル(imazalil)+SX、トリアジメノール(triadimenol)+SX、テトラコナゾール(tetraconazole)+SX、フルトリアホール(flutriafol)+SX、ブロムコナゾール(bromuconazole)+SX、プロピコナゾール(propiconazole)+SX、メフェントリフルコナゾール(mefentrifluconazole)+SX、イプフェントリフルコナゾール(ipfentrifluconazole)+SX、エポキシコナゾール(epoxiconazole)+SX、シプロコナゾール(cyproconazole)+SX、マンデストロビン(mandestrobin)+SX、アゾキシストロビン(azoxystrobin)+SX、ピラクロストロビン(pyraclostrobin)+SX、トリフロキシストロビン(trifloxystrobin)+SX、フルオキサストロビン(fluoxastrobin)+SX、ピコキシストロビン(picoxystrobin)+SX、フェナミドン(fenamidone)+SX、ジモキシストロビン(dimoxystrobin)+SX、メトミノストロビン(metominostrobin)+SX、ピリベンカルブ(pyribencarb)+SX、セダキサン(sedaxane)+SX、ペンフルフェン(penflufen)+SX、フルキサピロキサド(fluxapyroxad)+SX、フルオピラム(fluopyram)+SX、ベンゾビンジフルピル(benzovindiflupyr)+SX、ボスカリド(boscalid)+SX、カルボキシン(carboxin)+SX、ペンチオピラド(penthiopyrad)+SX、フルトラニル(flutolanil)+SX、ビキサフェン(bixafen)+SX、ピジフルメトフェン(pydiflumetofen)+SX、3-ジフルオロメチル-N-(7-フルオロ-1,1,3-トリメチルインダン-4-イル)-1-メチルピラゾール-4-カルボキサミド(1383809-87-7)+SX、N-シクロプロピル-3-(ジフルオロメチル)-5-フルオロ-N-(5-クロロ-2-イソプロピルベンジル)-1-メチル-1H-ピラゾール-4-カルボキサミド(1255734-28-1)+SX、3-ジフルオロメチル-1-メチル-N-(1,1,3-トリメチルインダン-4-イル)ピラゾール-4-カルボキサミド(141573-94-6)+SX、3-ジフルオロメチル-1-メチル-N-[(3R)-1,1,3-トリメチルインダン-4-イル]ピラゾール-4-カルボキサミド(1352994-67-2)+SX、メタラキシル(metalaxyl)+SX、メタラキシルM(metalaxyl-M)+SX、メトラフェノン(metrafenone)+SX、シフルフェナミド(cyflufenamid)+SX、プロキナジド(proquinazid)+SX、3-クロロ-5-フェニル-6-メチル-4-(2,6-ジフルオロフェニル)ピリダジン(1358061-55-8)+SX、1-(2-{[1-(4-クロロフェニル)-1H-ピラゾール-3-イル]オキシメチル}-3-メチルフェニル)-4-メチル-1,4-ジヒドロテトラゾール-5-オン(1472649-01-6)+SX、4-(2-ブロモ-4-フルオロフェニル)-N-(2-クロロ-6-フルオロフェニル)-1,3-ジメチル-1H-ピラゾール-5-アミン(1362477-26-6)+SX、フェンピコキサミド(fenpicoxamid)+SX、N’-(2,5-ジメチル-4-フェノキシフェニル)-N-エチル-N-メチルメタンイミドアミド(1052688-31-9)+SX、イソチアニル(isotianil)+SX、オキソリニック酸(oxolinic acid)+SX、フェリムゾン(ferimzone)+SX、フサライド(phthalide)+SX、カスガマイシン(kasugamycin)+SX、テブフロキン(tebufloquin)+SX、キノフメリン(quinofumelin)+SX、フェンピラザミン(fenpyrazamine)+SX、プロシミドン(procymidone)+SX、フルジオキソニル(fludioxonil)+SX、トルクロホスメチル(tolclofos-methyl)+SX、チアベンダゾール(thiabendazole)+SX、エタボキサム(ethaboxam)+SX、ピカルブトラゾクス(picarbutrazox)+SX、オキサチアピプロリン(oxathiapiprolin)+SX、イミノクタジン酢酸塩(iminoctadine triacetate)+SX、イミノクタジンアルベシル酸塩(iminoctadine albesilate)+SX、フェンプロピモルフ(fenpropimorph)+SX、フェンプロピジン(fenpropidin)+SX、スピロキサミン(spiroxamine)+SX、クロロタロニル(chlorothalonil)+SX、フォルペット(folpet)+SX、キャプタン(captan)+SX、チウラム(thiram)+SX、シルチオファム(silthiofam)+SX、マンコゼブ(mancozeb)+SX、カルタップ(cartap)+SX、クロチアニジン(clothianidin)+SX、チアメトキサム(thiamethoxam)+SX、イミダクロプリド(imidacloprid)+SX、チアクロプリド(thiacloprid)+SX、フルピラジフロン(flupyradifurone)+SX、スルホキサフロル(sulfoxaflor)+SX、トリフルメゾピリム(triflumezopyrim)+SX、ジクロロメゾチアズ(dicloromezotiaz)+SX、ベータシフルトリン(beta-cyfluthrin)+SX、テフルトリン(tefluthrin)+SX、フィプロニル(fipronil)+SX、クロラントラニリプロール(chlorantraniliprole)+SX、シアントラニリプロール(cyantraniliprole)+SX、テトラニリプロール(tetraniliprole)+SX、チオジカルブ(thiodicarb)+SX、カルボフラン(carbofuran)+SX、フルキサメタミド(fluxametamide)+SX、アフォキソラネル(afoxolaner)+SX、フルララネル(fluralaner)+SX、ブロフラニリド(broflanilide)+SX、アバメクチン(abamectin)+SX、フルエンスルホン(fluensulfone)+SX、フルアザインドリジン(fluazaindolizine)+SX、チオキサザフェン(tioxazafen)+SX、(E)-N-{1-[(6-クロロピリジン-3-イル)メチル]ピリジン-2(1H)-イリデン}-2,2,2-トリフルオロアセトアミド(1689566-03-7)+SX、菌根菌(Mycorrhizal Fungi)+SX、バチルス・フィルムス菌(Bacillus firmus)+SX、バチルス・アミロリケファシエンス菌(Bacillus amyloliquefaciens)+SX、パスツーリア・ニシザワエ菌(Pasteuria nishizawae)+SX、パスツーリア・ペネトランス菌(Pasteuria penetrans)+SX。
本発明化合物のいずれか1化合物50部、リグニンスルホン酸カルシウム3部、ラウリル硫酸マグネシウム2部及び合成含水酸化珪素45部をよく粉砕混合することにより、製剤を得る。
本発明化合物のいずれか1化合物20部とソルビタントリオレエート1.5部とを、ポリビニルアルコール2部を含む水溶液28.5部と混合し、湿式粉砕法で微粉砕した。その後、この中に、キサンタンガム0.05部及びアルミニウムマグネシウムシリケート0.1部を含む水溶液40部を加え、さらにプロピレングリコール10部を加えて攪拌混合し、製剤を得る。
本発明化合物のいずれか1化合物2部、カオリンクレー88部及びタルク10部をよく粉砕混合することにより、製剤を得る。
本発明化合物のいずれか1化合物5部、ポリオキシエチレンスチリルフェニルエーテル14部、ドデシルベンゼンスルホン酸カルシウム6部及びキシレン75部をよく混合することにより、製剤を得る。
本発明化合物のいずれか1化合物2部、合成含水酸化珪素1部、リグニンスルホン酸カルシウム2部、ベントナイト30部及びカオリンクレー65部をよく粉砕混合した後、水を加えてよく練り合せ、造粒乾燥することにより、製剤を得る。
ポリオキシエチレンアルキルエーテルサルフェートアンモニウム塩及びホワイトカーボンの混合物(重量比1:1)35部と、本発明化合物のいずれか1種20部と、水45部とを十分に混合し、製剤を得る。
プラスチックポットに土壌を詰め、そこにコムギ(品種;シロガネ)を播種し、温室内で9日間生育させた。製剤例6に記載の方法に準じて製剤化された本発明化合物(1)、本発明化合物(2)又は本発明化合物(3)を濃度が500ppmとなるように水と混合し、該混合物を、上記コムギの葉面に充分付着するように茎葉散布した。散布後コムギを風乾し、20℃、照明下で5日間栽培した後、コムギ赤さび病菌(Puccinia recondita)の胞子をふりかけ接種した。接種後コムギを23℃、暗黒多湿下に1日間置いた後、20℃、照明下で8日間栽培し、病斑面積を調査した。その結果、本発明化合物(1)、本発明化合物(2)又は本発明化合物(3)を処理したコムギにおける病斑面積はいずれも、無処理のコムギにおける病斑面積の10%以下であった。
プラスチックポットに土壌を詰め、そこにオオムギ(品種;ニシノホシ)を播種し、温室で7日間生育させた。製剤例6に記載の方法に準じて製剤化された本発明化合物(2)又は本発明化合物(3)を、濃度が500ppmとなるように水と混合し、該混合物を、上記オオムギの葉面に充分付着するように茎葉散布した。散布後オオムギを風乾し、2日後にオオムギ網斑病菌(Pyrenophora teres)胞子の水懸濁液を噴霧接種した。接種後オオムギを昼間23℃、夜間20℃の温室内で多湿下に3日間置き、次に温室内で7日間栽培した後、病斑面積を調査した。その結果、本発明化合物(2)又は本発明化合物(3)を処理したオオムギにおける病斑面積はいずれも、無処理のオオムギにおける病斑面積の10%以下であった。
Claims (6)
- 請求項1又は請求項2に記載のイミド化合物と、不活性担体とを含有する植物病害防除剤。
- 請求項1又は請求項2に記載のイミド化合物の有効量を植物又は土壌に処理することによる、植物病害防除方法。
- 植物病害を防除するための、請求項1又は請求項2に記載のイミド化合物の使用。
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WO2019168112A1 (ja) * | 2018-02-28 | 2019-09-06 | 北興化学工業株式会社 | イミド誘導体およびそれらを有効成分として含有する殺菌剤 |
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ZA201901475B (en) | 2020-09-30 |
MY190545A (en) | 2022-04-27 |
MX2019002431A (es) | 2019-07-04 |
UA121180C2 (uk) | 2020-04-10 |
JP6905987B2 (ja) | 2021-07-21 |
US11234439B2 (en) | 2022-02-01 |
PH12019500492A1 (en) | 2019-11-11 |
JPWO2018047670A1 (ja) | 2019-06-27 |
BR112019004304A2 (pt) | 2019-05-28 |
EP3511324A4 (en) | 2020-01-22 |
CN109661388B (zh) | 2021-11-26 |
KR20190043585A (ko) | 2019-04-26 |
IL265037B (en) | 2021-10-31 |
RU2019109978A (ru) | 2020-10-08 |
EP3511324B1 (en) | 2021-03-17 |
CA3036018A1 (en) | 2018-03-15 |
AU2017322952A1 (en) | 2019-04-04 |
AU2017322952B2 (en) | 2021-01-28 |
US20210274786A1 (en) | 2021-09-09 |
HUE054977T2 (hu) | 2021-10-28 |
BR112019004304B1 (pt) | 2022-09-20 |
EP3511324A1 (en) | 2019-07-17 |
PL3511324T3 (pl) | 2021-08-09 |
CN109661388A (zh) | 2019-04-19 |
KR102477723B1 (ko) | 2022-12-14 |
CL2019000572A1 (es) | 2019-06-21 |
DK3511324T3 (da) | 2021-04-12 |
CO2019002394A2 (es) | 2019-05-10 |
ES2870656T3 (es) | 2021-10-27 |
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