WO2024071440A1 - Cyclopropanecarboxylic acid ester compound and use thereof - Google Patents

Cyclopropanecarboxylic acid ester compound and use thereof Download PDF

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Publication number
WO2024071440A1
WO2024071440A1 PCT/JP2023/044005 JP2023044005W WO2024071440A1 WO 2024071440 A1 WO2024071440 A1 WO 2024071440A1 JP 2023044005 W JP2023044005 W JP 2023044005W WO 2024071440 A1 WO2024071440 A1 WO 2024071440A1
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composition
compound
group
compound according
diseases
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PCT/JP2023/044005
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French (fr)
Japanese (ja)
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康 片桐
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住友化学株式会社
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P3/00—Fungicides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C69/757—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety

Definitions

  • Patent Document 1 discloses a compound represented by the formula (A): The compound represented by the formula (hereinafter referred to as compound A) is described.
  • the objective of the present invention is to provide a compound that has excellent control effects against plant diseases.
  • the present inventors have conducted studies to find a compound having excellent control activity against plant diseases, and as a result have found that a compound represented by the following formula (I) has excellent control activity against plant diseases.
  • the present invention is as follows. [1] Formula (I) (hereinafter, referred to as the compound of the present invention). [2] A composition comprising the compound according to [1] and an inert carrier. [3] A method for controlling plant diseases, which comprises applying an effective amount of the compound according to [1] to plants or soil. [4] A composition comprising the compound according to [1] and one or more compounds selected from the group consisting of metofluthrin and dimefluthrin.
  • a composition comprising the compound according to [1] or the composition according to [4], and one or more liquid carriers selected from the group consisting of water, alcohols, ketones, aromatic hydrocarbons, aliphatic hydrocarbons, esters, nitriles, ethers, amides, halogenated hydrocarbons, sulfoxides, mineral oils, and vegetable oils.
  • a composition comprising the compound according to [1] or the composition according to [4], and one or more surfactants selected from the group consisting of alkyl sulfates, alkyl sulfonates, alkylaryl sulfonates, alkylaryl ethers, polyoxyethylated alkylaryl ethers, polyethylene glycol ethers, polyhydric alcohol esters, and sugar alcohol derivatives.
  • a composition comprising the compound according to [1] or the composition according to [4] and one or more thickeners selected from the group consisting of casein, gelatin, polysaccharides, lignin derivatives, bentonite, and synthetic water-soluble polymers.
  • BHT 2,6-di-t-butyl-4-methylphenol
  • BHA a mixture of 2-t-butyl-4-methoxyphenol and 3-t-butyl-4-methoxyphenol.
  • a composition comprising the compound according to [1] or the composition according to [4] supported on a plant powder.
  • composition in which the compound according to [1] or the composition according to [4] is supported on a thermoplastic resin or paper.
  • the present invention makes it possible to control plant diseases.
  • Stereoisomers include enantiomers and diastereomers.
  • the present invention includes each stereoisomer and mixtures of stereoisomers in any ratio.
  • the compound represented by formula (I') examples include those represented by the following formula:
  • the 2,2-dimethylcyclopropyl group is preferably in the 1R, trans form, ie, in the 1R,3R form, and such a compound is an optically active form represented by the formula (I').
  • the embodiments of the compound of the present invention include the following compounds.
  • a compound represented by formula (I') An optically active substance represented by formula (I') or an isomeric mixture rich in said optically active substance.
  • the composition according to one embodiment of the present invention is a composition containing the compound of the present invention and an inert carrier.
  • the composition is usually prepared by mixing the compound of the present invention with an inert carrier such as a solid carrier or a liquid carrier, and adding a surfactant or other formulation auxiliary as necessary to prepare an emulsion, oil, powder, granule, wettable powder, wettable granule, flowable, dry flowable, microcapsule, etc.
  • the composition generally contains the compound of the present invention in an amount of 0.0001 to 95% by weight based on the total weight of the composition.
  • Solid carriers used in formulation include, for example, fine powders and granules of clays (kaolin clay, diatomaceous earth, bentonite, acid clay, etc.), dry silica, wet silica, talc, ceramics, other inorganic minerals (sericite, quartz, sulfur, activated carbon, calcium carbonate, etc.), chemical fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride, etc.), and synthetic resins (polyester resins such as polypropylene, polyacrylonitrile, polymethylmethacrylate, polyethylene terephthalate, nylon resins such as nylon-6, nylon-11, nylon-66, polyamide resins, polyvinyl chloride, polyvinylidene chloride, vinyl chloride-propylene copolymers, etc.).
  • clays kaolin clay, diatomaceous earth, bentonite, acid clay, etc.
  • dry silica wet silica
  • Liquid carriers include, for example, water, alcohols (methanol, ethanol, etc.), ketones (acetone, methyl ethyl ketone, etc.), aromatic hydrocarbons (toluene, xylene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, etc.), esters (ethyl acetate, butyl acetate, etc.), nitriles (acetonitrile, etc.), ethers (diisopropyl ether, diethylene glycol dimethyl ether, etc.), amides (N,N-dimethylformamide, etc.), sulfoxides (dimethyl sulfoxide, etc.), and vegetable oils (soybean oil, cottonseed oil, etc.).
  • alcohols methanol, ethanol, etc.
  • ketones acetone, methyl ethyl ketone, etc.
  • aromatic hydrocarbons toluene, xylene, etc
  • Surfactants include, for example, nonionic surfactants such as polyoxyethylene alkyl ether or its salt (polyoxyethylene alkyl ether sulfate ammonium salt), polyoxyethylene alkyl aryl ether or its salt, polyethylene glycol fatty acid ester, and anionic surfactants such as alkyl sulfonates, alkyl benzene sulfonates, and alkyl sulfates.
  • nonionic surfactants such as polyoxyethylene alkyl ether or its salt (polyoxyethylene alkyl ether sulfate ammonium salt), polyoxyethylene alkyl aryl ether or its salt, polyethylene glycol fatty acid ester, and anionic surfactants such as alkyl sulfonates, alkyl benzene sulfonates, and alkyl sulfates.
  • formulation adjuvants include adhesives, dispersants, colorants, and stabilizers, such as casein, gelatin, sugars (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), isopropyl acid phosphate, BHT (2,6-di-tert-butyl-4-methylphenol), and BHA (a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol).
  • adhesives such as casein, gelatin, sugars (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), isopropyl acid phosphate, BHT
  • the compound of the present invention is effective against plant diseases caused by plant pathogenic microorganisms such as fungi, Oomycetes, Phytomyxea, and bacteria, and can control the plant diseases.
  • plant pathogenic microorganisms such as fungi, Oomycetes, Phytomyxea, and bacteria
  • fungi include Ascomycota, Basidiomycota, Blasocladiomycota, Chytridiomycota, Mucoromycota, and Olpidiomycota.
  • Specific examples include the following.
  • the names in parentheses indicate the scientific names of the plant pathogenic microorganisms that cause the diseases.
  • Rice diseases blast disease (Pyricularia oryzae, Magnaporthe grisea), brown leaf blight (Cochliobolus miyabeanus), sheath blight (Rhizoctonia solani), Gibberella fujikuroi, yellow dwarf disease (Sclerophthora macrospora), blast and panicle blight (Epicoccum nigrum), seedling damping-off (Trichoderma viride, Rhizopus oryzae), pseudo-sheath blight (Waitea circinata, Ceratobasidium setariae, Thanatephorus cucumeris); Wheat diseases: Powdery mildew (Blumeria graminis), Red mold (Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivale), Yellow rust (Puccinia striiformis), Black rust (Puccinia graminis), Red rust (Pucc
  • cucumber bacterial spot disease Pseudomonas syringae pv. lachrymans
  • eggplant bacterial wilt Ralstonia solanacearum
  • citrus canker disease Xanthomonas citri
  • Chinese cabbage soft rot disease Erwinia carotovora
  • potato scab disease Streptomyces scabiei
  • corn Goss's wilt disease Clavibacter michiganensis
  • grape olive, peach, etc.
  • Pierce's disease Xylella fastidiosa
  • crown gall disease Agrobacterium tumefaciens of Rosaceae plants such as apples, peaches, and cherries.
  • the method for controlling plant diseases of the present invention includes, for example, treatment of plants, such as spraying of foliage or seed disinfection, and treatment of areas where plants are cultivated, such as soil treatment.
  • the amount of the compound of the present invention to be applied is usually 1 to 10,000 g per 1,000 m2 of plant cultivation area.
  • the compound of the present invention is formulated as an emulsifiable concentrate, wettable powder, flowable agent or the like, it is usually applied after diluting with water so that the active ingredient concentration becomes 0.01 to 10,000 ppm (e.g., 1,000 ppm), and granules, dusts, etc. are usually applied as they are.
  • composition of the present invention can be used as a plant disease control agent in agricultural land such as fields, paddy fields, lawns, and orchards.
  • composition A is a composition (hereinafter referred to as composition A) containing the compound of the present invention and at least one compound selected from the group consisting of metofluthrin and dimefluthrin.
  • Metofluthrin and dimefluthrin can be used alone or in combination of two types.
  • metofluthrin and dimefluthrin each have one or more stereoisomers, and the metofluthrin and dimefluthrin used in the present invention include stereoisomers and mixtures thereof.
  • the ratio of the compound of the present invention to at least one compound selected from the group consisting of metofluthrin and dimefluthrin is not particularly limited, and may be, in terms of mass ratio (compound of the present invention:at least one compound selected from the group consisting of metofluthrin and dimefluthrin), 100,000:1 to 1:100,000, 50,000:1 to 1:50,000, Examples include 10,000:1 to 1:10,000, 1,000:1 to 1:1000, 500:1 to 1:500, 100:1 to 1:100, 50:1, 20:1, 10:1, 9:1, 8:1, 7:1, 6:1, 5:1, 4:1, 3:1, 2:1, 1:1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9, 1:10, 1:20, and 1:50.
  • composition A containing at least one compound selected from the group consisting of metofluthrin and dimefluthrin is expected to have excellent control effects against harmful arthropods.
  • harmful arthropods include the following.
  • Hemiptera pests planthoppers such as the striate brown planthopper, the brown planthopper, and the white-backed planthopper, leafhoppers such as the green rice leafhopper and the Taiwanese green rice leafhopper, aphids, stink bugs, whiteflies, scale insects, earwigs, psyllids, etc.;
  • Lepidoptera pests moths such as the rice stem borer, rice leaf borer, and Indian meal moth, cutworms such as the common cutworm, the armyworm, and the cutworm moth, butterflies such as the cabbage white butterfly, tortrix moths such as the small tortrix, fruit borer moths, leafminers, tussock moths, grasshoppers, Agrotis spp.
  • Dipteran pests Culex pipiens pallens, Culex tritaeniorhynchus, and other Culex pipiens, Aedes mosquitoes, Aedes aegypti, Aedes albopictus, and other Anopheles mosquitoes, Chironomids, House flies, Musca domestica, Musca domestica, and other blowflies, flesh flies, seed flies, little house flies, onion flies, and other flower flies, fruit flies, Drosophila melanogaster, moth flies, horseflies, black flies, stable flies, and the like; Coleoptera pests: corn rootworms such as Western corn rootworm and Southern corn rootworm, scarab beetles such as cupre be
  • Dictyoptera pests German cockroach, Smoky brown cockroach, American cockroach, Brown cockroach, Oriental cockroach, etc.
  • Thysanoptera pests Thrips palmi, Thrips occidentalis, Thrips palmi, etc.
  • Hymenoptera pests ants, hornets, ant wasps, sawflies such as turnip sawflies, etc.
  • Orthoptera pests mole crickets, grasshoppers, etc.
  • Siphonaptera pests human fleas, cat fleas, etc.
  • Phthiraptera pests body lice, pubic lice, etc.
  • Isoptera pests Reticulitermes speratus, Formosan termites, etc.
  • Indoor dust mites Dermatophagoides farinae, Dermatophagoides pteronys
  • composition B is usually prepared by mixing the compound of the present invention or composition A with a liquid carrier, a surfactant, etc., and adding formulation auxiliaries such as a thickener, a binder, a dispersant, a stabilizer, and a gas, if necessary, to be used as an oil solution, an emulsion, a wettable powder, a flowable agent (suspension in water, emulsion in water, etc.), a powder, a granule, an aerosol agent (direct spray type, space spray type, metered spray type, one-push type, total spray type, intermittent spray type, etc.), a spray, an electric spray (ultrasonic vibration type, electrostatic spray type, etc.), a heated transpiration agent (incense stick, electric mat, liquid-absorbing wick type heated transpiration agent, etc.), a non-heated transpiration agent (incense stick, electric mat, liquid-absorbing wick type heated transpiration agent, etc.), a non-heated transpiration agent (
  • a formulation that is one embodiment of the present invention is a formulation containing the compound of the present invention or Composition A, which is selected from the group consisting of an oil solution, an emulsion, a flowable agent, an aerosol agent, a heated evaporation agent, a non-heated evaporation agent, a fog agent, and a ULV agent.
  • These preparations usually contain the compound of the present invention or composition A in an amount of 0.0001 to 99% by weight based on the total weight of the preparation.
  • liquid carriers examples include water, alcohols (ethanol, cyclohexanol, benzyl alcohol, propylene glycol, polyethylene glycol, etc.), ketones (acetone, cyclohexanone, methyl ethyl ketone, etc.), aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, methylnaphthalene, phenylxylylethane, etc.), aliphatic hydrocarbons (hexane, cyclohexane, etc.), esters (ethyl acetate, butyl acetate, methyl oleate, etc.), nitriles (acetonitrile, isobutyronitrile, etc.), ethers (diisopropyl ether, dioxane, etc.), amides (N,N-dimethylformamide, N,N-dimethylacetamide, etc.), halogenated hydrocarbons (d
  • a composition according to one embodiment of the present invention is a composition containing the compound of the present invention or composition A and one or more liquid carriers selected from the group consisting of water, alcohols, ketones, aromatic hydrocarbons, aliphatic hydrocarbons, esters, nitriles, ethers, amides, halogenated hydrocarbons, sulfoxides, mineral oils, and vegetable oils.
  • a formulation according to one embodiment of the present invention is a formulation containing the composition and selected from the group consisting of oil solutions, emulsions, flowables, aerosols, heat evaporation agents, and ULV agents.
  • surfactant examples include alkyl sulfates, alkyl sulfonates, alkylaryl sulfonates, alkylaryl ethers, polyoxyethylated alkylaryl ethers, polyethylene glycol ethers, polyhydric alcohol esters, and sugar alcohol derivatives.
  • the composition according to one embodiment of the present invention is a composition containing the compound of the present invention or composition A and one or more surfactants selected from the group consisting of alkyl sulfates, alkyl sulfonates, alkylaryl sulfonates, alkylaryl ethers, polyoxyethylated alkylaryl ethers, polyethylene glycol ethers, polyhydric alcohol esters, and sugar alcohol derivatives.
  • the formulation according to one embodiment of the present invention is a formulation containing the composition and selected from the group consisting of emulsions, flowables, and heat-transferables.
  • a composition according to one embodiment of the present invention is a composition containing the compound of the present invention or composition A and one or more thickeners selected from the group consisting of casein, gelatin, polysaccharides, lignin derivatives, bentonite, and synthetic water-soluble polymers.
  • a formulation according to one embodiment of the present invention is a flowable preparation containing the composition.
  • Antioxidants include, for example, BHT (2,6-di-tert-butyl-4-methylphenol) and BHA (a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol).
  • a composition which is one embodiment of the present invention is a composition containing the compound of the present invention or composition A and one or more antioxidants selected from the group consisting of BHT and BHA.
  • a formulation which is one embodiment of the present invention is a formulation which contains the composition and is selected from the group consisting of oil solutions, emulsions, flowables, aerosols, heated transpiration agents, non-heated transpiration agents, aerosols, and ULV agents.
  • the composition according to one embodiment of the present invention is a composition in which the compound of the present invention or composition A is supported on a vegetable powder (wood flour, meal powder, etc.).
  • the vegetable powder may be used by mixing the vegetable powder with a binder (tab flour, starch, gluten, etc.).
  • the preparation according to one embodiment of the present invention is a heat-transpirable agent containing the composition.
  • a composition according to another embodiment of the present invention is a composition containing the compound of the present invention or composition A and a binder.
  • a preparation according to one embodiment of the present invention is a heat-transferable agent containing the composition.
  • the composition which is one embodiment of the present invention, is a composition in which the compound of the present invention or composition A is supported on one or more substrates selected from the group consisting of cotton linters and pulp.
  • substrates selected from the group consisting of cotton linters and pulp.
  • Specific examples of the substrate include cotton linters solidified into a plate shape and fibers of a mixture of cotton linters and pulp solidified into a plate shape.
  • the formulation which is one embodiment of the present invention, is a heat-transpirable agent containing the composition.
  • the composition according to one embodiment of the present invention is a composition in which the compound of the present invention or composition A is supported on a resin or paper.
  • the preparation according to one embodiment of the present invention is a non-heated evaporative agent containing the composition.
  • the resin include polyethylene resins such as low-density polyethylene, linear low-density polyethylene, and high-density polyethylene; ethylene-vinyl ester copolymers such as ethylene-vinyl acetate copolymer; ethylene-methacrylic acid ester copolymers such as ethylene-methyl methacrylate copolymer and ethylene-ethyl methacrylate copolymer; ethylene-acrylic acid ester copolymers such as ethylene-methyl acrylate copolymer and ethylene-ethyl acrylate copolymer; ethylene-vinyl carboxylic acid copolymers such as ethylene-acrylic acid copolymer; ethylene-tetracyclododecen
  • compositions may be used alone or in combination of two or more. If necessary, plasticizers such as phthalates (dimethyl phthalate, dioctyl phthalate, and the like), adipic acid esters, and stearic acid may be added to these resins.
  • plasticizers such as phthalates (dimethyl phthalate, dioctyl phthalate, and the like), adipic acid esters, and stearic acid may be added to these resins.
  • the paper include filter paper and Japanese paper.
  • Another embodiment of the composition of the present invention is a composition in which the compound of the present invention or Composition A is supported on a resin.
  • a composition which is yet another embodiment of the present invention is a composition in which the compound of the present invention or composition A is supported on paper.
  • Test Example 1 35 parts by weight of a mixture of polyoxyethylene alkyl ether sulfate ammonium salt and silica (weight ratio 1:1), 10 parts by weight of the compound of the present invention, and 55 parts by weight of water were mixed and finely ground by a wet grinding method to obtain a preparation.
  • the obtained preparation was mixed with water to obtain a mixture containing 1000 ppm of the compound of the present invention.
  • Plastic pots were filled with soil, rice (variety: Hinohikari) was sown therein, and cultivated in a greenhouse for 20 days. The mixture obtained was then sprayed on the stems and leaves of the rice so that it was sufficiently attached to the leaf surface of the rice.
  • the rice was air-dried, and the sprayed rice was placed in contact with rice seedlings (variety: Hinohikari) infected with rice blast fungus (Magnaporthe grisea) for 6 days under high humidity at 24°C during the day and 20°C at night, and the lesion area was then examined.
  • the lesion area in the rice treated with the compound of the present invention was 10% or less of that in the untreated rice, where "untreated" means that the mixture containing the compound of the present invention was not sprayed.
  • the compound of the present invention exhibits excellent control effects against plant diseases.

Abstract

The present invention provides a compound having excellent control efficacy against plant diseases. The compound, represented by formula (I), has excellent control efficacy against plant diseases.

Description

シクロプロパンカルボン酸エステル化合物及びその用途Cyclopropane carboxylic acid ester compounds and their uses
　本特許出願は、日本国特許出願２０２３－０２４１８６号（２０２３年２月２０日出願）に基づくパリ条約上の優先権および利益を主張するものであり、ここに引用することによって、上記出願に記載された内容の全体が本明細書中に組み込まれるものとする。
　本発明はシクロプロパンカルボン酸エステル化合物及びその用途に関する。 This patent application claims priority and the benefit of Japanese Patent Application No. 2023-024186 (filed February 20, 2023) under the Paris Convention, the entire contents of which are incorporated herein by reference.
The present invention relates to a cyclopropane carboxylic acid ester compound and its use.
　これまでに植物病害の防除を目的として、様々な化合物が検討されており、実用に供されている（非特許文献１参照）。一方で、特許文献１には、家庭防疫用途に優れた効力を有する化合物として式（Ａ）：
Figure JPOXMLDOC01-appb-C000002
 で示される化合物（以下、化合物Ａと記す）が記載されている。 Various compounds have been studied and put to practical use for the purpose of controlling plant diseases (see Non-Patent Document 1). On the other hand, Patent Document 1 discloses a compound represented by the formula (A):
Figure JPOXMLDOC01-appb-C000002
 The compound represented by the formula (hereinafter referred to as compound A) is described.
特開２００１－１１０２２号公報JP 2001-11022 A
　本発明は、植物病害に対して優れた防除効力を有する化合物を提供することを課題とする。 The objective of the present invention is to provide a compound that has excellent control effects against plant diseases.
　本発明者は、植物病害に対する優れた防除効力を有する化合物を見出すべく検討の結果、下記式（Ｉ）で示される化合物が、植物病害に対して優れた防除効力を有することを見出した。
　本発明は、以下のとおりである。
［１］　式（Ｉ）
Figure JPOXMLDOC01-appb-C000003
 で示される化合物（以下、本発明化合物と記す）。
［２］　［１］に記載の化合物と、不活性担体とを含有する組成物。
［３］　［１］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。
［４］　［１］に記載の化合物と、メトフルトリン及びジメフルトリンからなる群より選ばれる１以上の化合物とを含有する組成物。
［５］　［１］に記載の化合物又は［４］に記載の組成物と、水、アルコール類、ケトン類、芳香族炭化水素類、脂肪族炭化水素類、エステル類、ニトリル類、エーテル類、アミド類、ハロゲン化炭化水素類、スルホキシド類、鉱物油類、及び植物油類からなる群より選ばれる１以上の液体担体とを含有する組成物。
［６］　［１］に記載の化合物又は［４］に記載の組成物と、アルキル硫酸エステル塩、アルキルスルホン酸塩、アルキルアリールスルホン酸塩、アルキルアリールエーテル類、アルキルアリールエーテル類のポリオキシエチレン化物、ポリエチレングリコールエーテル類、多価アルコールエステル類、及び糖アルコール誘導体からなる群より選ばれる１以上の界面活性剤とを含有する組成物。
［７］　［１］に記載の化合物又は［４］に記載の組成物と、カゼイン、ゼラチン、多糖類、リグニン誘導体、ベントナイト、及び合成水溶性高分子からなる群より選ばれる１以上の増粘剤とを含有する組成物。
［８］　［１］に記載の化合物又は［４］に記載の組成物と、ＢＨＴ（２，６－ジ－ｔ－ブチル－４－メチルフェノール）、及びＢＨＡ（２－ｔ－ブチル－４－メトキシフェノールと３－ｔ－ブチル－４－メトキシフェノールとの混合物）からなる群より選ばれる１以上の酸化防止剤とを含有する組成物。
［９］　［１］に記載の化合物又は［４］に記載の組成物を、植物性粉末に担持させた組成物。
［１０］　［１］に記載の化合物又は［４］に記載の組成物と、結合剤とを含有する組成物。
［１１］　［１］に記載の化合物又は［４］に記載の組成物を、コットンリンター及びパルプからなる群より選ばれる１以上の基材に担持させた組成物。
［１２］　［１］に記載の化合物又は［４］に記載の組成物を、熱可塑性樹脂、又は紙に担持させた組成物。
［１３］　［４］～［１２］のいずれか１項に記載の組成物を含有する、油剤、乳剤、フロアブル剤、エアゾール剤、加熱蒸散剤、非加熱蒸散剤、煙霧剤、及びＵＬＶ剤からなる群より選ばれる製剤。 Means of the Invention The present inventors have conducted studies to find a compound having excellent control activity against plant diseases, and as a result have found that a compound represented by the following formula (I) has excellent control activity against plant diseases.
The present invention is as follows.
[1] Formula (I)
Figure JPOXMLDOC01-appb-C000003
 (hereinafter, referred to as the compound of the present invention).
[2] A composition comprising the compound according to [1] and an inert carrier.
[3] A method for controlling plant diseases, which comprises applying an effective amount of the compound according to [1] to plants or soil.
[4] A composition comprising the compound according to [1] and one or more compounds selected from the group consisting of metofluthrin and dimefluthrin.
[5] A composition comprising the compound according to [1] or the composition according to [4], and one or more liquid carriers selected from the group consisting of water, alcohols, ketones, aromatic hydrocarbons, aliphatic hydrocarbons, esters, nitriles, ethers, amides, halogenated hydrocarbons, sulfoxides, mineral oils, and vegetable oils.
[6] A composition comprising the compound according to [1] or the composition according to [4], and one or more surfactants selected from the group consisting of alkyl sulfates, alkyl sulfonates, alkylaryl sulfonates, alkylaryl ethers, polyoxyethylated alkylaryl ethers, polyethylene glycol ethers, polyhydric alcohol esters, and sugar alcohol derivatives.
[7] A composition comprising the compound according to [1] or the composition according to [4] and one or more thickeners selected from the group consisting of casein, gelatin, polysaccharides, lignin derivatives, bentonite, and synthetic water-soluble polymers.
[8] A composition containing the compound according to [1] or the composition according to [4], and one or more antioxidants selected from the group consisting of BHT (2,6-di-t-butyl-4-methylphenol) and BHA (a mixture of 2-t-butyl-4-methoxyphenol and 3-t-butyl-4-methoxyphenol).
[9] A composition comprising the compound according to [1] or the composition according to [4] supported on a plant powder.
[10] A composition comprising the compound according to [1] or the composition according to [4] and a binder.
[11] A composition comprising the compound according to [1] or the composition according to [4] supported on one or more substrates selected from the group consisting of cotton linters and pulp.
[12] A composition in which the compound according to [1] or the composition according to [4] is supported on a thermoplastic resin or paper.
[13] A formulation containing the composition according to any one of [4] to [12], the formulation being selected from the group consisting of an oil solution, an emulsion, a flowable agent, an aerosol agent, a heated evaporation agent, a non-heated evaporation agent, a fog agent, and a ULV agent.
　本発明により、植物病害を防除することができる。 The present invention makes it possible to control plant diseases.
　本発明化合物は、一つ以上の立体異性体が存在する。立体異性体としては、エナンチオマー及びジアステレオマーが挙げられる。本発明には各立体異性体及び任意の比率の立体異性体混合物が含まれる。 The compound of the present invention exists in one or more stereoisomers. Stereoisomers include enantiomers and diastereomers. The present invention includes each stereoisomer and mixtures of stereoisomers in any ratio.
　立体異性体としては、例えば、式（Ｉ’）:
Figure JPOXMLDOC01-appb-C000004
 で示される化合物が挙げられる。
　２，２－ジメチルシクロプロピル基は、１Ｒ，ｔｒａｎｓ体、即ち、１Ｒ，３Ｒ体であることが好ましく、かかる化合物は式（Ｉ’）で示される光学活性体である。
　本発明化合物として、式（Ｉ’）で示される光学活性体又は該光学活性体を多く含む異性体混合物を使用するのが好ましい。 As a stereoisomer, for example, the compound represented by formula (I'):
Figure JPOXMLDOC01-appb-C000004
 Examples of the compound include those represented by the following formula:
The 2,2-dimethylcyclopropyl group is preferably in the 1R, trans form, ie, in the 1R,3R form, and such a compound is an optically active form represented by the formula (I').
As the compound of the present invention, it is preferable to use an optically active substance represented by formula (I') or a mixture of isomers rich in said optically active substance.
　本発明化合物の態様として、以下の化合物が挙げられる。
　式（Ｉ’）で示される化合物。
　式（Ｉ’）で示される光学活性体又は該光学活性体を多く含む異性体混合物。 The embodiments of the compound of the present invention include the following compounds.
A compound represented by formula (I'):
An optically active substance represented by formula (I') or an isomeric mixture rich in said optically active substance.
　本発明の１つの実施形態である組成物は、本発明化合物と不活性担体とを含有する組成物である。前記組成物は、通常、本発明化合物と固体担体、液体担体等の不活性担体とを混合し、必要に応じて界面活性剤、その他の製剤用補助剤を添加して、乳剤、油剤、粉剤、粒剤、水和剤、顆粒水和剤、フロアブル剤、ドライフロアブル剤、マイクロカプセル剤等に製剤化される。
　前記組成物は、本発明化合物を通常、組成物の総重量に対して、０．０００１～９５重量％含有する。 The composition according to one embodiment of the present invention is a composition containing the compound of the present invention and an inert carrier. The composition is usually prepared by mixing the compound of the present invention with an inert carrier such as a solid carrier or a liquid carrier, and adding a surfactant or other formulation auxiliary as necessary to prepare an emulsion, oil, powder, granule, wettable powder, wettable granule, flowable, dry flowable, microcapsule, etc.
The composition generally contains the compound of the present invention in an amount of 0.0001 to 95% by weight based on the total weight of the composition.
　製剤化の際に用いられる固体担体としては、例えば粘土類（カオリンクレー、珪藻土、ベントナイト、酸性白土等）、乾式シリカ、湿式シリカ、タルク、セラミック、その他の無機鉱物（セリサイト、石英、硫黄、活性炭、炭酸カルシウム等）、化学肥料（硫安、燐安、硝安、尿素、塩安等）等の微粉末及び粒状物等、並びに合成樹脂（ポリプロピレン、ポリアクリロニトリル、ポリメタクリル酸メチル、ポリエチレンテレフタレート等のポリエステル樹脂、ナイロン－６、ナイロン－１１、ナイロン－６６等のナイロン樹脂、ポリアミド樹脂、ポリ塩化ビニル、ポリ塩化ビニリデン、塩化ビニル－プロピレン共重合体等）が挙げられる。 Solid carriers used in formulation include, for example, fine powders and granules of clays (kaolin clay, diatomaceous earth, bentonite, acid clay, etc.), dry silica, wet silica, talc, ceramics, other inorganic minerals (sericite, quartz, sulfur, activated carbon, calcium carbonate, etc.), chemical fertilizers (ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ammonium chloride, etc.), and synthetic resins (polyester resins such as polypropylene, polyacrylonitrile, polymethylmethacrylate, polyethylene terephthalate, nylon resins such as nylon-6, nylon-11, nylon-66, polyamide resins, polyvinyl chloride, polyvinylidene chloride, vinyl chloride-propylene copolymers, etc.).
　液体担体としては、例えば水、アルコール類（メタノール、エタノール等）、ケトン類（アセトン、メチルエチルケトン等）、芳香族炭化水素類（トルエン、キシレン等）、脂肪族炭化水素類（ヘキサン、シクロヘキサン等）、エステル類（酢酸エチル、酢酸ブチル等）、ニトリル類（アセトニトリル等）、エーテル類（ジイソプロピルエーテル、ジエチレングリコールジメチルエーテル等）、アミド類（Ｎ，Ｎ－ジメチルホルムアミド等）、スルホキシド類（ジメチルスルホキシド等）、及び植物油（大豆油、綿実油等）が挙げられる。 Liquid carriers include, for example, water, alcohols (methanol, ethanol, etc.), ketones (acetone, methyl ethyl ketone, etc.), aromatic hydrocarbons (toluene, xylene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, etc.), esters (ethyl acetate, butyl acetate, etc.), nitriles (acetonitrile, etc.), ethers (diisopropyl ether, diethylene glycol dimethyl ether, etc.), amides (N,N-dimethylformamide, etc.), sulfoxides (dimethyl sulfoxide, etc.), and vegetable oils (soybean oil, cottonseed oil, etc.).
　界面活性剤としては、例えばポリオキシエチレンアルキルエーテルもしくはその塩（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）、ポリオキシエチレンアルキルアリールエーテルもしくはその塩、ポリエチレングリコール脂肪酸エステル等の非イオン界面活性剤、及びアルキルスルホン酸塩、アルキルベンゼンスルホン酸塩、アルキル硫酸塩等の陰イオン界面活性剤が挙げられる。 Surfactants include, for example, nonionic surfactants such as polyoxyethylene alkyl ether or its salt (polyoxyethylene alkyl ether sulfate ammonium salt), polyoxyethylene alkyl aryl ether or its salt, polyethylene glycol fatty acid ester, and anionic surfactants such as alkyl sulfonates, alkyl benzene sulfonates, and alkyl sulfates.
　その他の製剤用補助剤としては、固着剤、分散剤、着色剤及び安定剤等、具体的には例えばカゼイン、ゼラチン、糖類（でんぷん、アラビアガム、セルロース誘導体、アルギン酸等）、リグニン誘導体、ベントナイト、合成水溶性高分子（ポリビニルアルコール、ポリビニルピロリドン、ポリアクリル酸類等）、酸性リン酸イソプロピル、ＢＨＴ（２，６－ジ－ｔｅｒｔ－ブチル－４－メチルフェノール）、ＢＨＡ（２－ｔｅｒｔ－ブチル－４－メトキシフェノールと３－ｔｅｒｔ－ブチル－４－メトキシフェノールとの混合物）が挙げられる。 Other formulation adjuvants include adhesives, dispersants, colorants, and stabilizers, such as casein, gelatin, sugars (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), isopropyl acid phosphate, BHT (2,6-di-tert-butyl-4-methylphenol), and BHA (a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol).
　本発明化合物は、真菌（fungi）、卵菌(Oomycete)、ネコブカビ(Phytomyxea)、細菌(bacteria)等の植物病原性微生物が引き起こす植物病害に対して効力を有し、該植物病害を防除することができる。真菌（fungi）としては、例えば、子嚢菌門（Ascomycota）、担子菌門（Basidiomycota）、Blasocladiomycota、Chytridiomycota、Mucoromycota、及びOlpidiomycotaが挙げられる。具体的には、例えば、以下のものが挙げられる。括弧内は、その病害を引き起こす植物病原性微生物の学名を示す。 The compound of the present invention is effective against plant diseases caused by plant pathogenic microorganisms such as fungi, Oomycetes, Phytomyxea, and bacteria, and can control the plant diseases. Examples of fungi include Ascomycota, Basidiomycota, Blasocladiomycota, Chytridiomycota, Mucoromycota, and Olpidiomycota. Specific examples include the following. The names in parentheses indicate the scientific names of the plant pathogenic microorganisms that cause the diseases.
　イネの病害：いもち病（Pyricularia oryzae、Magnaporthe grisea）、ごま葉枯病（Cochliobolus miyabeanus）、紋枯病（Rhizoctonia solani）、馬鹿苗病（Gibberella fujikuroi）、黄化萎縮病（Sclerophthora macrospora）、にせいもち病及び穂枯病（Epicoccum nigrum）、苗立枯病（Trichoderma viride、Rhizopus oryzae）、疑似紋枯症（赤色菌核病菌（Waitea circinata）、褐色菌核病菌（Ceratobasidium setariae）、褐色紋枯病菌（Thanatephorus cucumeris））；
　コムギの病害：うどんこ病（Blumeria graminis）、赤かび病（Fusarium graminearum、Fusarium avenaceum、Fusarium culmorum、Microdochium nivale）、黄さび病（Puccinia striiformis）、黒さび病（Puccinia graminis）、赤さび病（Puccinia recondita）、紅色雪腐病（Microdochium nivale、Microdochium majus）、雪腐小粒菌核病（Typhula incarnata、Typhula ishikariensis）、雪腐大粒菌核病（Sclerotinia borealis）、褐色雪腐病（Pythium spp.）裸黒穂病（Ustilago tritici）、なまぐさ黒穂病（Tilletia caries、Tilletia controversa）、眼紋病（Pseudocercosporella herpotrichoides）、葉枯病（Septoria tritici）、ふ枯病（Stagonospora nodorum）、黄斑病（Pyrenophora tritici-repentis）、リゾクトニア属菌による苗立枯れ病（Rhizoctonia solani）、立枯病（Gaeumannomyces graminis）、いもち病（Pyricularia graminis-tritici）；
　オオムギの病害：うどんこ病（Blumeria graminis）、赤かび病（Fusarium graminearum、Fusarium avenaceum、Fusarium culmorum、Microdochium nivale）、黄さび病（Puccinia striiformis）、黒さび病（Puccinia graminis）、小さび病（Puccinia hordei）、裸黒穂病（Ustilago nuda）、雲形病（Rhynchosporium secalis）、網斑病（Pyrenophora teres）、斑点病（Cochliobolus sativus）、斑葉病（Pyrenophora graminea）、ラムラリアリーフスポット病（Ramularia collo-cygni）、リゾクトニア属菌による苗立枯れ病（Rhizoctonia solani）；
　トウモロコシの病害：さび病（Puccinia sorghi）、南方さび病（Puccinia polysora）、すす紋病（Setosphaeria turcica）、熱帯性さび病（Physopella zeae）、ごま葉枯病（Cochliobolus heterostrophus）、炭疽病（Colletotrichum graminicola）、グレーリーフスポット病（Cercospora zeae-maydis）、褐斑病（Kabatiella zeae）、ファエオスファエリアリーフスポット病（Phaeosphaeria maydis）、Diplodia病（Stenocarpella maydis、Stenocarpella macrospora）、ストークロット病（Fusarium graminearum、Fusarium verticilioides、Colletotrichum graminicola）、黒穂病（Ustilago maydis）、フイソデルマ病（Physoderma maydis）、tar spot病(Phyllachora maydis)；
　ワタの病害：炭疽病（Colletotrichum gossypii）、白かび病（Ramularia areola）、黒斑病（Alternaria macrospora、Alternaria gossypii）、Black root rot病 (Thielaviopsis basicola）；
　コーヒーの病害：さび病（Hemileia vastatrix）、リーフスポット病（Cercospora coffeicola)；
　ナタネの病害：菌核病（Sclerotinia sclerotiorum）、黒斑病（Alternaria brassicae）、根朽病（Phoma lingam）、light leaf spot病（Pyrenopeziza brassicae）；
　サトウキビの病害：さび病（Puccinia melanocephela、Puccinia kuehnii）、黒穂病 (Ustilago scitaminea）；
　ヒマワリの病害：さび病（Puccinia helianthi）、べと病（Plasmopara halstedii）；
　カンキツ類の病害：黒点病（Diaporthe citri）、そうか病（Elsinoe fawcetti）、緑かび病（Penicillium digitatum）、青かび病（Penicillium italicum）、疫病（Phytophthora parasitica、Phytophthora citrophthora）、こうじかび病（Aspergillus niger）；
　リンゴの病害：モニリア病（Monilinia mali）、腐らん病（Valsa ceratosperma）、うどんこ病（Podosphaera leucotricha）、斑点落葉病（Alternaria alternata apple pathotype）、黒星病（Venturia inaequalis）、炭疽病（Glomerella cingulata、Colletotrichum acutatum）、褐斑病（Diplocarpon mali）、輪紋病（Botryosphaeria berengeriana）、疫病（Phytophtora cactorum）、赤星病（Gymnosporangium juniperi-virginianae、Gymnosporangium yamadae）；
　ナシの病害：黒星病（Venturia nashicola、Venturia pirina）、黒斑病（Alternaria alternata Japanese pear pathotype）、赤星病（Gymnosporangium haraeanum）；
　モモの病害：灰星病（Monilinia fructicola）、黒星病（Cladosporium carpophilum）、ホモプシス腐敗病（Phomopsis sp.）、縮葉病（Taphrina deformans）；
　ブドウの病害：黒とう病（Elsinoe ampelina）、晩腐病（Glomerella cingulata、Colletotrichum acutatum）、うどんこ病（Uncinula necator）、さび病（Neophysopella sp.）、ブラックロット病（Guignardia bidwellii）、べと病（Plasmopara viticola）；
　カキの病害：炭疽病（Gloeosporium kaki、Colletotrichum acutatum）、落葉病（Cercospora kaki、Mycosphaerella nawae）；
　イチジクの病害：さび病（Phakopsora nishidana）；
　ウリ類の病害：炭疽病（Colletotrichum lagenarium）、うどんこ病（Sphaerotheca fuliginea）、つる枯病（Didymella bryoniae）、褐斑病（Corynespora cassiicola）、つる割病（Fusarium oxysporum）、べと病（Pseudoperonospora cubensis）、疫病（Phytophthora capsici）、苗立枯病（Pythium sp.）、ホモプシス根腐病（Phomopsis sp.）；
　トマトの病害：輪紋病（Alternaria solani）、葉かび病（Cladosporium fulvum）、すすかび病（Pseudocercospora fuligena）、疫病（Phytophthora infestans）、うどんこ病（Leveillula taurica）；
　ナスの病害：褐紋病（Phomopsis vexans）、うどんこ病（Erysiphe cichoracearum）；
　アブラナ科野菜の病害：黒斑病（Alternaria japonica）、白斑病（Cercosporella brassicae）、根こぶ病（Plasmodiophora brassicae）、べと病（Peronospora parasitica）、白さび病（Albugo candida）；
　ネギの病害：さび病（Puccinia allii）、黒斑病（Alternaria porri）、黒腐菌核病(Sclerotium cepivorum)、小菌核腐敗病（Botrytis squamosa）；
　ダイズの病害：紫斑病（Cercospora kikuchii）、黒とう病（Elsinoe glycines）、黒点病（Diaporthe phaseolorum var. sojae）、さび病（Phakopsora pachyrhizi)、褐色輪紋病（Corynespora cassiicola）、炭疽病（Colletotrichum glycines、Colletotrichum truncatum）、葉腐病（Rhizoctonia solani）、褐紋病（Septoria glycines）、斑点病（Cercospora sojina）、菌核病（Sclerotinia sclerotiorum）、うどんこ病（Microsphaera diffusa）、茎疫病（Phytophthora sojae）、べと病（Peronospora manshurica）、突然死病（Fusarium virguliforme）、黒根腐病（Calonectria ilicicola）、Diaporthe/Phomopsis complex（Diaporthe longicolla）；
　インゲンの病害：菌核病（Sclerotinia sclerotiorum）、さび病（Uromyces appendiculatus）、角斑病（Phaeoisariopsis griseola）、炭疽病（Colletotrichum lindemuthianum）、根腐病（Fusarium solani）；
　ラッカセイの病害：黒渋病（Cercospora personata）、褐斑病（Cercospora arachidicola）、白絹病（Sclerotium rolfsii）、黒根腐病（Calonectria ilicicola）；
　エンドウの病害：うどんこ病（Erysiphe pisi）、根腐病（Fusarium solani）；
　ジャガイモの病害：夏疫病（Alternaria solani）、疫病（Phytophthora infestans）、緋色腐敗病（Phytophthora erythroseptica）、粉状そうか病（Spongospora subterranea f. sp. subterranea）、半身萎凋病（Verticillium albo－atrum、Verticillium dahliae、Verticillium nigrescens）、乾腐病（Fusarium solani）、がん腫病（Synchytrium endobioticum）；
　イチゴの病害：うどんこ病（Sphaerotheca humuli）、炭疽病（Glomerella cingulata、Colletotrichum acutatum）；
　チャの病害：網もち病（Exobasidium reticulatum）、白星病（Elsinoe leucospila）、輪斑病（Pestalotiopsis sp.）、炭疽病（Colletotrichum theae－sinensis）；
　タバコの病害：赤星病（Alternaria longipes）、炭疽病（Colletotrichum tabacum）、べと病（Peronospora tabacina）、疫病（Phytophthora nicotianae）；
　テンサイの病害：褐斑病（Cercospora beticola）、葉腐病（Thanatephorus cucumeris）、根腐病（Thanatephorus cucumeris）、黒根病（Aphanomyces cochlioides）、さび病（Uromyces betae）；
　バラの病害：黒星病（Diplocarpon rosae）、うどんこ病（Sphaerotheca pannosa）；
　キクの病害：褐斑病（Septoria chrysanthemi-indici）、白さび病（Puccinia horiana）；
　タマネギの病害：白斑葉枯病（Botrytis cinerea、Botrytis byssoidea、Botrytis squamosa)、灰色腐敗病（Botrytis allii）、小菌核性腐敗病（Botrytis squamosa）；
　種々の作物の病害：灰色かび病（Botrytis cinerea）、菌核病（Sclerotinia sclerotiorum）、黒腐菌核病(Sclerotium cepivorum)、白絹病（Sclerotium rolfsii）苗立枯病（Pythium aphanidermatum、Pythium irregulare、Pythium ultimum）；
　ダイコンの病害：黒斑病（Alternaria brassicicola）；
　シバの病害：ダラースポット病（Sclerotinia homoeocarpa）、ブラウンパッチ病、ラージパッチ病（Rhizoctonia solani）、赤焼病（Pythium aphanidermatum）；
　バナナの病害：シガトカ病（Mycosphaerella fijiensis、Mycosphaerella musicola）;
　レンズマメの病害：Ascochyta病（Ascochyta lentis）;
　ヒヨコマメの病害：Ascochyta病（Ascochyta rabiei）;
　ピーマンの病害：炭疽病（Colletotrichum scovillei）；
　マンゴーの病害：炭疽病（Colletotrichum acutatum）；
　かんしょの病害：基腐病（Diaporthe destruens）；
　果樹の病害：白紋羽病（Rosellinia necatrix）、紫紋羽病（Helicobasidium mompa）；
　収穫後のリンゴ、ナシ等の果実の病害：ムコールロット病（Mucor piriformis）；
Aspergillus属、Penicillium属、Fusarium属、Gibberella属、Tricoderma属、Thielaviopsis属、Rhizopus属、Mucor属、Corticium属、Phoma属、Rhizoctonia属、Diplodia属等によって引き起こされる、種子病害又は生育初期の病害；
　ウイルス病：Olpidium brassicaeによって媒介されるレタスのビッグベイン病、Polymyxa属（例えば、Polymyxa betae及びPolymyxa graminis）によって媒介される各種作物のウイルス病；
　細菌(bacteria)が引き起こす病害：イネの苗立枯細菌病（Burkholderia plantarii）、イネの内穎褐変病（Pantoea ananatis）、イネの白葉枯病（Xanthomonas oryzae pv. oryzae.）、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）、ジャガイモのそうか病（Streptomyces scabiei）、トウモロコシのGoss's wilt病（Clavibacter michiganensis）、ブドウ、オリーブ、モモ等のピアス病（Xylella fastidiosa）、リンゴ、モモ、サクランボ等のバラ科植物の根頭がんしゅ病（Agrobacterium tumefaciens）。 Rice diseases: blast disease (Pyricularia oryzae, Magnaporthe grisea), brown leaf blight (Cochliobolus miyabeanus), sheath blight (Rhizoctonia solani), Gibberella fujikuroi, yellow dwarf disease (Sclerophthora macrospora), blast and panicle blight (Epicoccum nigrum), seedling damping-off (Trichoderma viride, Rhizopus oryzae), pseudo-sheath blight (Waitea circinata, Ceratobasidium setariae, Thanatephorus cucumeris);
Wheat diseases: 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 recondita), Pink snow mold (Microdochium nivale, Microdochium majus), Snow mold sclerotinia (Typhula incarnata, Typhula ishikariensis), Snow mold sclerotinia (Sclerotinia borealis), Brown snow mold (Pythium spp.), Bark smut (Ustilago tritici), Cattle smut (Tilletia caries, Tilletia controversa), Eyespot (Pseudocercosporella herpotrichoides), Leaf blight (Septoria tritici), blight (Stagonospora nodorum), yellow spot (Pyrenophora tritici-repentis), seedling damping-off (Rhizoctonia solani), damping-off (Gaeumannomyces graminis), blast (Pyricularia graminis-tritici);
Barley diseases: powdery mildew (Blumeria graminis), red mold (Fusarium graminearum, Fusarium avenaceum, Fusarium culmorum, Microdochium nivale), yellow rust (Puccinia striiformis), black rust (Puccinia graminis), small rust (Puccinia hordei), bare smut (Ustilago nuda), scald (Rhynchosporium secalis), net blotch (Pyrenophora teres), spot (Cochliobolus sativus), spotted leaf (Pyrenophora graminea), leaf spot (Ramularia collo-cygni), damping-off (Rhizoctonia solani);
Corn diseases: rust (Puccinia sorghi), southern rust (Puccinia polysora), sooty leaf spot (Setosphaeria turcica), tropical rust (Physopella zeae), brown spot (Cochliobolus heterostrophus), anthracnose (Colletotrichum graminicola), gray leaf spot (Cercospora zeae-maydis), brown spot (Kabatiella zeae), Phaeosphaeria leaf spot (Phaeosphaeria maydis), Diplodia disease (Stenocarpella maydis, Stenocarpella macrospora), stalk rot (Fusarium graminearum, Fusarium verticilioides, Colletotrichum graminicola), smut (Ustilago maydis), Physoderma maydis, tar spot (Phyllachora maydis);
Cotton diseases: Anthracnose (Colletotrichum gossypii), White mold (Ramularia areola), Black spot (Alternaria macrospora, Alternaria gossypii), Black root rot (Thielaviopsis basicola);
Coffee diseases: Rust (Hemileia vastatrix), Leaf spot (Cercospora coffeicola);
Rapeseed diseases: Sclerotinia sclerotiorum, Alternaria brassicae, Phoma lingam, light leaf spot (Pyrenopeziza brassicae);
Sugarcane diseases: rust (Puccinia melanocephela, Puccinia kuehnii), smut (Ustilago scitaminea);
Sunflower diseases: Rust (Puccinia helianthi), Downy mildew (Plasmopara halstedii);
Citrus diseases: black spot (Diaporthe citri), scab (Elsinoe fawcetti), green mold (Penicillium digitatum), blue mold (Penicillium italicum), late blight (Phytophthora parasitica, Phytophthora citrophthora), aspergillus niger;
Apple diseases: Monilinia mali, canker (Valsa ceratosperma), powdery mildew (Podosphaera leucotricha), leaf spot (Alternaria alternata apple pathotype), black spot (Venturia inaequalis), anthracnose (Glomerella cingulata, Colletotrichum acutatum), brown spot (Diplocarpon mali), ring spot (Botryosphaeria berengeriana), late blight (Phytophtora cactorum), red spot (Gymnosporangium juniperi-virginianae, Gymnosporangium yamadae);
Pear diseases: black spot (Venturia nashicola, Venturia pirina), black spot (Alternaria alternata Japanese pear pathotype), red spot (Gymnosporangium haraeanum);
Peach diseases: Brown spot (Monilinia fructicola), Black spot (Cladosporium carpophilum), Phomopsis rot (Phomopsis sp.), Leaf curl (Taphrina deformans);
Grape diseases: black rot (Elsinoe ampelina), late rot (Glomerella cingulata, Colletotrichum acutatum), powdery mildew (Uncinula necator), rust (Neophysopella sp.), black rot (Guignardia bidwellii), downy mildew (Plasmopara viticola);
Persimmon diseases: anthracnose (Gloeosporium kaki, Colletotrichum acutatum), leaf spot (Cercospora kaki, Mycosphaerella nawae);
Fig Diseases: Rust (Phakopsora nishidana);
Cucurbit diseases: Anthracnose (Colletotrichum lagenarium), Powdery mildew (Sphaerotheca fuliginea), Blight (Didymella bryoniae), Brown spot (Corynespora cassiicola), Blight (Fusarium oxysporum), Downy mildew (Pseudoperonospora cubensis), Late blight (Phytophthora capsici), Seedling damping off (Pythium sp.), Phomopsis root rot (Phomopsis sp.);
Tomato diseases: Alternaria solani, Cladosporium fulvum, Pseudocercospora fuligena, Phytophthora infestans, powdery mildew;
Eggplant diseases: brown spot (Phomopsis vexans), powdery mildew (Erysiphe cichoracearum);
Diseases of cruciferous vegetables: black spot (Alternaria japonica), white spot (Cercosporella brassicae), clubroot (Plasmodiophora brassicae), downy mildew (Peronospora parasitica), white rust (Albugo candida);
Diseases of leeks: rust (Puccinia allii), black spot (Alternaria porri), black rot (Sclerotium cepivorum), small sclerotinia rot (Botrytis squamosa);
Soybean diseases: Purple spot (Cercospora kikuchii), black rot (Elsinoe glycines), black spot (Diaporthe phaseolorum var. sojae), rust (Phakopsora pachyrhizi), brown spot (Corynespora cassiicola), anthracnose (Colletotrichum glycines, Colletotrichum truncatum), leaf rot (Rhizoctonia solani), brown spot (Septoria glycines), leaf spot (Cercospora sojina), sclerotinia sclerotiorum, powdery mildew (Microsphaera diffusa), stem rot (Phytophthora sojae), downy mildew (Peronospora manshurica), sudden death (Fusarium virguliforme), black root rot (Calonectria ilicicola), Diaporthe/Phomopsis complex (Diaporthe longicolla);
Diseases of beans: Sclerotinia sclerotiorum, rust (Uromyces appendiculatus), angular spot (Phaeoisariopsis griseola), anthracnose (Colletotrichum lindemuthianum), root rot (Fusarium solani);
Peanut diseases: black leaf spot (Cercospora personata), brown spot (Cercospora arachidicola), white rot (Sclerotium rolfsii), black root rot (Calonectria ilicicola);
Pea diseases: powdery mildew (Erysiphe pisi), root rot (Fusarium solani);
Potato diseases: Alternaria solani, Phytophthora infestans, Phytophthora erythroseptica, Spongospora subterranea f. sp. subterranea, Verticillium albo-atrum, Verticillium dahliae, Verticillium nigrescens, Fusarium solani, Synchytrium endobioticum;
Strawberry diseases: Powdery mildew (Sphaerotheca humuli), anthracnose (Glomerella cingulata, Colletotrichum acutatum);
Tea diseases: net blight (Exobasidium reticulatum), white spot (Elsinoe leucospila), ring spot (Pestalotiopsis sp.), anthracnose (Colletotrichum theae-sinensis);
Tobacco diseases: red spot (Alternaria longipes), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina), late blight (Phytophthora nicotianae);
Sugar beet diseases: brown spot (Cercospora beticola), leaf rot (Thanatephorus cucumeris), root rot (Thanatephorus cucumeris), black root (Aphanomyces cochlioides), rust (Uromyces betae);
Rose diseases: black spot (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa);
Chrysanthemum diseases: brown spot (Septoria chrysanthemi-indici), white rust (Puccinia horiana);
Onion diseases: white spotted leaf spot (Botrytis cinerea, Botrytis byssoidea, Botrytis squamosa), grey rot (Botrytis allii), small sclerotinia rot (Botrytis squamosa);
Diseases of various crops: gray mold (Botrytis cinerea), sclerotinia sclerotiorum, black rot (Sclerotium cepivorum), white mold (Sclerotium rolfsii), damping-off (Pythium aphanidermatum, Pythium irregulare, Pythium ultimum);
Diseases of radish: Black spot (Alternaria brassicicola);
Turfgrass diseases: Dollar spot disease (Sclerotinia homoeocarpa), Brown patch disease, Large patch disease (Rhizoctonia solani), Red burn disease (Pythium aphanidermatum);
Banana diseases: Sigatoka disease (Mycosphaerella fijiensis, Mycosphaerella musicola);
Lentil diseases: Ascochyta disease (Ascochyta lentis);
Chickpea diseases: Ascochyta disease (Ascochyta rabiei);
Pepper diseases: Anthracnose (Colletotrichum scovillei);
Mango diseases: Anthracnose (Colletotrichum acutatum);
Diseases of sweet potato: Root rot (Diaporthe destruens);
Fruit tree diseases: White root rot (Rosellinia necatrix), Purple root rot (Helicobasidium mompa);
Post-harvest diseases of apples, pears, and other fruits: Mucor rot (Mucor piriformis);
Seed diseases or diseases in the early growth stage caused by the genera Aspergillus, Penicillium, Fusarium, Gibberella, Tricoderma, Thielaviopsis, Rhizopus, Mucor, Corticium, Phoma, Rhizoctonia, Diplodia, etc.;
Viral diseases: big vein disease of lettuce transmitted by Olpidium brassicae, viral diseases of various crops transmitted by the genus Polymyxa (e.g., Polymyxa betae and Polymyxa graminis);
Diseases caused by bacteria: rice seedling bacterial blight (Burkholderia plantarii), rice inner lemma browning disease (Pantoea ananatis), rice white leaf blight (Xanthomonas oryzae pv. oryzae.), cucumber bacterial spot disease (Pseudomonas syringae pv. lachrymans), eggplant bacterial wilt (Ralstonia solanacearum), citrus canker disease (Xanthomonas citri), Chinese cabbage soft rot disease (Erwinia carotovora), potato scab disease (Streptomyces scabiei), corn Goss's wilt disease (Clavibacter michiganensis), grape, olive, peach, etc. Pierce's disease (Xylella fastidiosa), and crown gall disease (Agrobacterium tumefaciens) of Rosaceae plants such as apples, peaches, and cherries.
　本発明の植物病害の防除方法は、例えば茎葉散布、種子消毒等の植物体への処理；土壌処理等の植物の栽培地への処理が挙げられる。 The method for controlling plant diseases of the present invention includes, for example, treatment of plants, such as spraying of foliage or seed disinfection, and treatment of areas where plants are cultivated, such as soil treatment.
　本発明化合物の処理量は、植物の栽培地の１０００ｍ2あたり通常１～１００００ｇである。本発明化合物が乳剤、水和剤、フロアブル剤等に製剤化されている場合は、通常、有効成分濃度が０．０１～１００００ｐｐｍ（例えば１０００ｐｐｍ）となるように水で希釈して施用し、粒剤、粉剤等は、通常、そのまま施用する。 The amount of the compound of the present invention to be applied is usually 1 to 10,000 g per 1,000 m2 of plant cultivation area. When the compound of the present invention is formulated as an emulsifiable concentrate, wettable powder, flowable agent or the like, it is usually applied after diluting with water so that the active ingredient concentration becomes 0.01 to 10,000 ppm (e.g., 1,000 ppm), and granules, dusts, etc. are usually applied as they are.
　本発明の組成物は、畑、水田、芝生、果樹園等の農耕地における植物病害の防除剤として使用することができる。 The composition of the present invention can be used as a plant disease control agent in agricultural land such as fields, paddy fields, lawns, and orchards.
　本発明の１つの実施形態である組成物は、本発明化合物と、メトフルトリン（metofluthrin）及びジメフルトリン（dimefluthrin）からなる群より選ばれる少なくとも１つの化合物とを含有する組成物（以下、組成物Ａと記す）である。メトフルトリン及びジメフルトリンは、一種のみで、又は、二種を組み合わせて、使用できる。また、メトフルトリン及びジメフルトリンには、それぞれ一つ以上の立体異性体が存在するが、本発明で使用されるメトフルトリン及びジメフルトリンには、立体異性体及びその混合物が含まれる。
　組成物Ａにおいて、本発明化合物と、メトフルトリン及びジメフルトリンからなる群より選ばれる少なくとも１つの化合物との比は、特に限定されるものではないが、質量比（本発明化合物：メトフルトリン及びジメフルトリンからなる群より選ばれる少なくとも１つの化合物）で、１０００００：１～１：１０００００、５００００：１～１：５００００、１００００：１～１：１００００、１０００：１～１：１０００、５００：１～１：５００、１００：１～１：１００、５０：１、２０：１、１０：１、９：１、８：１、７：１、６：１、５：１、４：１、３：１、２：１、１：１、１：２、１：３、１：４、１：５、１：６、１：７、１：８、１：９、１：１０、１：２０、及び１：５０等が挙げられる。 A composition according to one embodiment of the present invention is a composition (hereinafter referred to as composition A) containing the compound of the present invention and at least one compound selected from the group consisting of metofluthrin and dimefluthrin. Metofluthrin and dimefluthrin can be used alone or in combination of two types. In addition, metofluthrin and dimefluthrin each have one or more stereoisomers, and the metofluthrin and dimefluthrin used in the present invention include stereoisomers and mixtures thereof.
In composition A, the ratio of the compound of the present invention to at least one compound selected from the group consisting of metofluthrin and dimefluthrin is not particularly limited, and may be, in terms of mass ratio (compound of the present invention:at least one compound selected from the group consisting of metofluthrin and dimefluthrin), 100,000:1 to 1:100,000, 50,000:1 to 1:50,000, Examples include 10,000:1 to 1:10,000, 1,000:1 to 1:1000, 500:1 to 1:500, 100:1 to 1:100, 50:1, 20:1, 10:1, 9:1, 8:1, 7:1, 6:1, 5:1, 4:1, 3:1, 2:1, 1:1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9, 1:10, 1:20, and 1:50.
　メトフルトリン及びジメフルトリンは、それぞれ、有害昆虫、有害ダニ類等の有害節足動物に対し優れた防除効果を発揮することが知られている。そのため、メトフルトリン及びジメフルトリンからなる群より選ばれる少なくとも１つの化合物を含有する組成物Ａは、有害節足動物に対し優れた防除効果を発揮することも期待できる。有害節足動物としては、例えば、以下のものが挙げられる。
　半翅目害虫：ヒメトビウンカ、トビイロウンカ、セジロウンカ等のウンカ類、ツマグロヨコバイ、タイワンツマグロヨコバイ等のヨコバイ類、アブラムシ類、カメムシ類、コナジラミ類、カイガラムシ類、グンバイムシ類、キジラミ類等；
　鱗翅目害虫：ニカメイガ、コブノメイガ、ノシメコクガ等のメイガ類、ハスモンヨトウ、アワヨトウ、ヨトウガ等のヨトウ類、モンシロチョウ等のシロチョウ類、コカクモンハマキ等のハマキガ類、シンクイガ類、ハモグリガ類、ドクガ類、ウワバ類、カブラヤガ、タマナヤガ等のアグロティス属害虫（Ａｇｒｏｔｉｓ　ｓｐｐ．）、ヘリコベルパ属害虫（Ｈｅｌｉｃｏｖｅｒｐａ　ｓｐｐ．）ヘリオティス属害虫（Ｈｅｌｉｏｔｈｉｓ ｓｐｐ．）、コナガ、イチモンジセセリ、イガ、コイガ等；
　双翅目害虫：アカイエカ、コガタアカイエカ等のイエカ類、ネッタイシマカ、ヒトスジシマカ等のヤブカ類、シナハマダラカ等のハマダラカ類、ユスリカ類、イエバエ、オオイエバエ等のイエバエ類、クロバエ類、ニクバエ類、タネバエ、ヒメイエバエ、タマネギバエ等のハナバエ類、ミバエ類、ショウジョウバエ類、チョウバエ類、アブ類、ブユ類、サシバエ類等；
　鞘翅目害虫：ウエスタンコーンルートワーム、サザンコーンルートワーム等のコーンルートワーム類、ドウガネブイブイ、ヒメコガネ等のコガネムシ類、コクゾウムシ、イネミズゾウムシ、ワタミゾウムシ、アズキゾウムシ等のゾウムシ類、チャイロコメノゴミムシダマシ、コクヌストモドキ等のゴミムシダマシ類、イネドロオイムシ、キスジノミハムシ、ウリハムシ等のハムシ類、シバンムシ類、ニジュウヤホシテントウ等のエピラクナ属（Ｅｐｉｌａｃｈｎａ　ｓｐｐ．）、ヒラタキクイムシ類、ナガシンクイムシ類、カミキリムシ類、アオバアリガタハネカクシ等；
　網翅目害虫：チャバネゴキブリ、クロゴキブリ、ワモンゴキブリ、トビイロゴキブリ、コバネゴキブリ等；
　総翅目害虫：ミナミキイロアザミウマ、ミカンキイロアザミウマ、ハナアザミウマ等；
　膜翅目害虫：アリ類、スズメバチ類、アリガタバチ類、カブラハバチ等のハバチ類等；
　直翅目害虫：ケラ、バッタ等；
　隠翅目害虫：ヒトノミ、ネコノミ等；
　シラミ目害虫：ヒトジラミ、ケジラミ等；
　等翅目害虫：ヤマトシロアリ、イエシロアリ等；
　屋内塵性ダニ類：コナヒョウヒダニ、ヤケヒョウヒダニ等のヒョウヒダニ類、ケナガコナダニ、ムギコナダニ等のコナダニ類、チリニクダニ、イエニクダニ、サヤアシニクダニ等のニクダニ類、クワガタツメダニ、フトツメダニ等のツメダニ類、ホコリダニ類、マルニクダニ類、イエササラダニ類、ハダニ類、フタトゲチマダニ等のマダニ類、ナミハダニ、カンザワハダニ、ミカンハダニ、リンゴハダニ等。
　有害節足動物は、殺虫剤、殺ダニ剤等に薬剤感受性の低下した、又は薬剤抵抗性の発達した有害節足動物であってもよい。 Metofluthrin and dimefluthrin are known to have excellent control effects against harmful arthropods such as harmful insects and harmful mites. Therefore, composition A containing at least one compound selected from the group consisting of metofluthrin and dimefluthrin is expected to have excellent control effects against harmful arthropods. Examples of harmful arthropods include the following.
Hemiptera pests: planthoppers such as the striate brown planthopper, the brown planthopper, and the white-backed planthopper, leafhoppers such as the green rice leafhopper and the Taiwanese green rice leafhopper, aphids, stink bugs, whiteflies, scale insects, earwigs, psyllids, etc.;
Lepidoptera pests: moths such as the rice stem borer, rice leaf borer, and Indian meal moth, cutworms such as the common cutworm, the armyworm, and the cutworm moth, butterflies such as the cabbage white butterfly, tortrix moths such as the small tortrix, fruit borer moths, leafminers, tussock moths, grasshoppers, Agrotis spp. such as the turnip cutworm and the burr moth, Helicoverpa spp., Heliothis spp., diamondback moth, skipper butterfly, burr moth, and the like;
Dipteran pests: Culex pipiens pallens, Culex tritaeniorhynchus, and other Culex pipiens, Aedes mosquitoes, Aedes aegypti, Aedes albopictus, and other Anopheles mosquitoes, Chironomids, House flies, Musca domestica, Musca domestica, and other blowflies, flesh flies, seed flies, little house flies, onion flies, and other flower flies, fruit flies, Drosophila melanogaster, moth flies, horseflies, black flies, stable flies, and the like;
Coleoptera pests: corn rootworms such as Western corn rootworm and Southern corn rootworm, scarab beetles such as cupre beetle and dung beetle, weevils such as rice weevils, rice water weevils, cotton weevils, and azuki bean weevils, meal beetles such as brown meal beetles and red flour beetles, leaf beetles such as rice leaf beetles, yellow flea beetles, and cucumber beetles, Epilachna spp. such as 200-spotted ladybird beetles, flat-headed wood beetles, long-horned beetles, and green leaf beetles;
Dictyoptera pests: German cockroach, Smoky brown cockroach, American cockroach, Brown cockroach, Oriental cockroach, etc.;
Thysanoptera pests: Thrips palmi, Thrips occidentalis, Thrips palmi, etc.;
Hymenoptera pests: ants, hornets, ant wasps, sawflies such as turnip sawflies, etc.;
Orthoptera pests: mole crickets, grasshoppers, etc.;
Siphonaptera pests: human fleas, cat fleas, etc.;
Phthiraptera pests: body lice, pubic lice, etc.;
Isoptera pests: Reticulitermes speratus, Formosan termites, etc.;
Indoor dust mites: Dermatophagoides farinae, Dermatophagoides pteronyssinus, and other dust mites; grain mites such as Acaridae putrescentiae and Acorn mites; flesh mites such as Acaridae dust mites, Acaridae house mites, and Acaridae legumes; chigger mites such as Acanthogneisseria gonorrhoeae and Acaridae foot mites; dust mites, Acaridae mites, Ophiopogonidae, spider mites, mites such as Haemaphysalis longicornis, two-spotted spider mites, Kanzawa spider mites, citrus red mite, apple red mite, and the like.
The harmful arthropod may be an arthropod having reduced sensitivity to insecticides, acaricides, etc., or having developed resistance to such drugs.
　本発明化合物又は組成物Ａは、通常、さらに不活性担体を含有する組成物（以下、組成物Ｂと記す）として使用する。組成物Ｂは、通常、本発明化合物又は組成物Ａと液体担体、界面活性剤等とを混合し、必要により、増粘剤、結合剤、分散剤、安定剤、ガス等の製剤用補助剤を添加して、油剤、乳剤、水和剤、フロアブル剤（水中懸濁剤、水中乳濁剤等）、粉剤、粒剤、エアゾール剤（直撃噴霧型、空間噴霧型、定量噴霧型、ワンプッシュ型、全量噴霧型、間欠噴霧型等）、スプレー剤、電気式噴霧剤（超音波振動式、静電噴霧式等）、加熱蒸散剤（線香、電気マット、吸液芯型加熱蒸散剤等）、非加熱蒸散剤（樹脂蒸散剤、含浸紙蒸散剤、ネット製剤等）、煙霧剤（フォギング等）、ＵＬＶ（Ultra Low Volume）剤等に用いることができる。
　本発明の１つの実施形態である製剤は、本発明化合物又は組成物Ａを含有する、油剤、乳剤、フロアブル剤、エアゾール剤、加熱蒸散剤、非加熱蒸散剤、煙霧剤、及びＵＬＶ剤からなる群より選ばれる製剤である。
　これらの製剤には本発明化合物又は組成物Ａが、製剤の総重量に対して、重量比で通常０．０００１～９９％含有される。 The compound of the present invention or composition A is usually used as a composition further containing an inert carrier (hereinafter referred to as composition B). Composition B is usually prepared by mixing the compound of the present invention or composition A with a liquid carrier, a surfactant, etc., and adding formulation auxiliaries such as a thickener, a binder, a dispersant, a stabilizer, and a gas, if necessary, to be used as an oil solution, an emulsion, a wettable powder, a flowable agent (suspension in water, emulsion in water, etc.), a powder, a granule, an aerosol agent (direct spray type, space spray type, metered spray type, one-push type, total spray type, intermittent spray type, etc.), a spray, an electric spray (ultrasonic vibration type, electrostatic spray type, etc.), a heated transpiration agent (incense stick, electric mat, liquid-absorbing wick type heated transpiration agent, etc.), a non-heated transpiration agent (resin transpiration agent, impregnated paper transpiration agent, net preparation, etc.), a fog agent (fogging, etc.), ULV (Ultra Low Volume) agent, etc.
A formulation that is one embodiment of the present invention is a formulation containing the compound of the present invention or Composition A, which is selected from the group consisting of an oil solution, an emulsion, a flowable agent, an aerosol agent, a heated evaporation agent, a non-heated evaporation agent, a fog agent, and a ULV agent.
These preparations usually contain the compound of the present invention or composition A in an amount of 0.0001 to 99% by weight based on the total weight of the preparation.
　液体担体としては、例えば、水、アルコール類（エタノール、シクロヘキサノール、ベンジルアルコール、プロピレングリコール、ポリエチレングリコール等）、ケトン類（アセトン、シクロヘキサノン、メチルエチルケトン等）、芳香族炭化水素類（ベンゼン、トルエン、キシレン、エチルベンゼン、メチルナフタレン、フェニルキシリルエタン等）、脂肪族炭化水素類（ヘキサン、シクロヘキサン等）、エステル類（酢酸エチル、酢酸ブチル、オレイン酸メチル等）、ニトリル類（アセトニトリル、イソブチロニトリル等）、エーテル類（ジイソプロピルエーテル、ジオキサン等）、アミド類（Ｎ，Ｎ－ジメチルホルムアミド、Ｎ，Ｎ－ジメチルアセトアミド等）、ハロゲン化炭化水素類（ジクロロメタン、トリクロロメタン、四塩化炭素等）、スルホキシド類（ジメチルスルホキシド等）、ラクタム類（Ｎ－メチルピロリドン、Ｎ－オクチルピロリドン等）、脂肪酸類（オレイン酸等）、鉱物油類（ケロシン、灯油、軽油等）、及び植物油類（大豆油、綿実油等）が挙げられる。
　本発明の１つの実施形態である組成物は、本発明化合物又は組成物Ａと、水、アルコール類、ケトン類、芳香族炭化水素類、脂肪族炭化水素類、エステル類、ニトリル類、エーテル類、アミド類、ハロゲン化炭化水素類、スルホキシド類、鉱物油類、及び植物油類からなる群より選ばれる１以上の液体担体とを含有する組成物である。また、本発明の１つの実施形態である製剤は、当該組成物を含有する、油剤、乳剤、フロアブル剤、エアゾール剤、加熱蒸散剤、及びＵＬＶ剤からなる群より選ばれる製剤である。 Examples of liquid carriers include water, alcohols (ethanol, cyclohexanol, benzyl alcohol, propylene glycol, polyethylene glycol, etc.), ketones (acetone, cyclohexanone, methyl ethyl ketone, etc.), aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, methylnaphthalene, phenylxylylethane, etc.), aliphatic hydrocarbons (hexane, cyclohexane, etc.), esters (ethyl acetate, butyl acetate, methyl oleate, etc.), nitriles (acetonitrile, isobutyronitrile, etc.), ethers (diisopropyl ether, dioxane, etc.), amides (N,N-dimethylformamide, N,N-dimethylacetamide, etc.), halogenated hydrocarbons (dichloromethane, trichloromethane, carbon tetrachloride, etc.), sulfoxides (dimethyl sulfoxide, etc.), lactams (N-methylpyrrolidone, N-octylpyrrolidone, etc.), fatty acids (oleic acid, etc.), mineral oils (kerosene, kerosene, diesel, etc.), and vegetable oils (soybean oil, cottonseed oil, etc.).
A composition according to one embodiment of the present invention is a composition containing the compound of the present invention or composition A and one or more liquid carriers selected from the group consisting of water, alcohols, ketones, aromatic hydrocarbons, aliphatic hydrocarbons, esters, nitriles, ethers, amides, halogenated hydrocarbons, sulfoxides, mineral oils, and vegetable oils. A formulation according to one embodiment of the present invention is a formulation containing the composition and selected from the group consisting of oil solutions, emulsions, flowables, aerosols, heat evaporation agents, and ULV agents.
　界面活性剤としては、例えば、アルキル硫酸エステル塩、アルキルスルホン酸塩、アルキルアリールスルホン酸塩、アルキルアリールエーテル類、アルキルアリールエーテル類のポリオキシエチレン化物、ポリエチレングリコールエーテル類、多価アルコールエステル類、及び糖アルコール誘導体が挙げられる。
　本発明の１つの実施形態である組成物は、本発明化合物又は組成物Ａと、アルキル硫酸エステル塩、アルキルスルホン酸塩、アルキルアリールスルホン酸塩、アルキルアリールエーテル類、アルキルアリールエーテル類のポリオキシエチレン化物、ポリエチレングリコールエーテル類、多価アルコールエステル類、及び糖アルコール誘導体からなる群より選ばれる１以上の界面活性剤とを含有する組成物である。また、本発明の１つの実施形態である製剤は、当該組成物を含有する、乳剤、フロアブル剤、及び加熱蒸散剤からなる群より選ばれる製剤である。 Examples of the surfactant include alkyl sulfates, alkyl sulfonates, alkylaryl sulfonates, alkylaryl ethers, polyoxyethylated alkylaryl ethers, polyethylene glycol ethers, polyhydric alcohol esters, and sugar alcohol derivatives.
The composition according to one embodiment of the present invention is a composition containing the compound of the present invention or composition A and one or more surfactants selected from the group consisting of alkyl sulfates, alkyl sulfonates, alkylaryl sulfonates, alkylaryl ethers, polyoxyethylated alkylaryl ethers, polyethylene glycol ethers, polyhydric alcohol esters, and sugar alcohol derivatives. Also, the formulation according to one embodiment of the present invention is a formulation containing the composition and selected from the group consisting of emulsions, flowables, and heat-transferables.
　増粘剤としては、例えば、カゼイン、ゼラチン、多糖類（デンプン、アラビアガム、セルロース誘導体、アルギン酸等）、リグニン誘導体、ベントナイト、及び合成水溶性高分子（ポリビニルアルコール、ポリビニルピロリドン、ポリアクリル酸類等）が挙げられる。
　本発明の１つの実施形態である組成物は、本発明化合物又は組成物Ａと、カゼイン、ゼラチン、多糖類、リグニン誘導体、ベントナイト、及び合成水溶性高分子からなる群より選ばれる１以上の増粘剤とを含有する組成物である。また、本発明の１つの実施形態である製剤は、当該組成物を含有する、フロアブル剤である。 Examples of thickeners include casein, gelatin, polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, and synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.).
A composition according to one embodiment of the present invention is a composition containing the compound of the present invention or composition A and one or more thickeners selected from the group consisting of casein, gelatin, polysaccharides, lignin derivatives, bentonite, and synthetic water-soluble polymers. A formulation according to one embodiment of the present invention is a flowable preparation containing the composition.
　酸化防止剤としては、例えば、ＢＨＴ（２，６－ジ－ｔｅｒｔ－ブチル－４－メチルフェノール）、及びＢＨＡ（２－ｔｅｒｔ－ブチル－４－メトキシフェノールと３－ｔｅｒｔ－ブチル－４－メトキシフェノールとの混合物）が挙げられる。
　本発明の１つの実施形態である組成物は、本発明化合物又は組成物Ａと、ＢＨＴ及びＢＨＡからなる群より選ばれる１以上の酸化防止剤とを含有する組成物である。また、本発明の１つの実施形態である製剤は、当該組成物を含有する、油剤、乳剤、フロアブル剤、エアゾール剤、加熱蒸散剤、非加熱蒸散剤、煙霧剤、及びＵＬＶ剤からなる群より選ばれる製剤である。 Antioxidants include, for example, BHT (2,6-di-tert-butyl-4-methylphenol) and BHA (a mixture of 2-tert-butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol).
A composition which is one embodiment of the present invention is a composition containing the compound of the present invention or composition A and one or more antioxidants selected from the group consisting of BHT and BHA. Also, a formulation which is one embodiment of the present invention is a formulation which contains the composition and is selected from the group consisting of oil solutions, emulsions, flowables, aerosols, heated transpiration agents, non-heated transpiration agents, aerosols, and ULV agents.
　本発明の１つの実施形態である組成物は、本発明化合物又は組成物Ａを、植物性粉末（木粉、粕粉等）に担持させた組成物である。植物性粉末は、前記植物性粉末と結合剤（タブ粉、スターチ、グルテン等）とを混合して用いてもよい。また、本発明の１つの実施形態である製剤は、当該組成物を含有する、加熱蒸散剤である。
　本発明のまた別の実施形態である組成物は、本発明化合物又は組成物Ａと、結合剤とを含有する組成物である。また、本発明の１つの実施形態である製剤は、当該組成物を含有する、加熱蒸散剤である。 The composition according to one embodiment of the present invention is a composition in which the compound of the present invention or composition A is supported on a vegetable powder (wood flour, meal powder, etc.). The vegetable powder may be used by mixing the vegetable powder with a binder (tab flour, starch, gluten, etc.). The preparation according to one embodiment of the present invention is a heat-transpirable agent containing the composition.
A composition according to another embodiment of the present invention is a composition containing the compound of the present invention or composition A and a binder. A preparation according to one embodiment of the present invention is a heat-transferable agent containing the composition.
　本発明の１つの実施形態である組成物は、本発明化合物又は組成物Ａを、コットンリンター及びパルプからなる群より選ばれる１以上の基材に担持させた組成物である。前記基材は、具体的には、例えば、コットンリンターを板状に固めたもの及びコットンリンターとパルプとの混合物の繊維を板状に固めたものが挙げられる。また、本発明の１つの実施形態である製剤は、当該組成物を含有する、加熱蒸散剤である。 The composition, which is one embodiment of the present invention, is a composition in which the compound of the present invention or composition A is supported on one or more substrates selected from the group consisting of cotton linters and pulp. Specific examples of the substrate include cotton linters solidified into a plate shape and fibers of a mixture of cotton linters and pulp solidified into a plate shape. In addition, the formulation, which is one embodiment of the present invention, is a heat-transpirable agent containing the composition.
　本発明の１つの実施形態である組成物は、本発明化合物又は組成物Ａを、樹脂又は紙に担持させた組成物である。また、本発明の１つの実施形態である製剤は、当該組成物を含有する、非加熱蒸散剤である。
　前記樹脂としては、例えば、低密度ポリエチレン、直鎖状低密度ポリエチレン、高密度ポリエチレン等のポリエチレン樹脂；エチレン－酢酸ビニル共重合体等のエチレン－ビニルエステル共重合体；エチレン－メタクリル酸メチル共重合体、エチレン－メタクリル酸エチル共重合体等のエチレン－メタクリル酸エステル共重合体；エチレン－アクリル酸メチル共重合体、エチレン－アクリル酸エチル共重合体等のエチレン－アクリル酸エステル共重合体；エチレン－アクリル酸共重合体等のエチレン－ビニルカルボン酸共重合体；エチレン－テトラシクロドデセン共重合体；プロピレン重合体、プロピレン－エチレン共重合体のポリプロピレン樹脂；ポリ－４－メチルペンテン－１、ポリブテン－１、ポリブタジエン、ポリスチレン、アクリロニトリル－スチレン樹脂；アクリロニトリル－ブタジエン－スチレン樹脂、スチレン－共役ジエン共重合体、スチレン－共役ジエンブロック共重合体水素添加物等のスチレン系エラストマー；フッ素樹脂；ポリメタクリル酸メチル等のアクリル酸樹脂；ナイロン６、ナイロン６６等のポリアミド樹脂；ポリエチレンテレフタレート、ポリエチレンナフタレート、ポリブチレンテレフタレート、ポリシクロへキシレンジメチレンテレフタレート等のポリエステル樹脂；ポリカーボネート、ポリアセタール、ポリアクリルサルフォン、ポリアリレート、ヒドロキシ安息香酸ポリエステル、ポリエーテルイミド、ポリエステルカーボネート、ポリフェニレンエーテル樹脂、ポリ塩化ビニル、ポリ塩化ビニリデン、ポリウレタンが挙げられ、これらの樹脂は、単独で用いても２種以上の混合物として用いてもよい。これらの樹脂には、必要により、フタル酸エステル類（フタル酸ジメチル、フタル酸ジオクチル等）、アジピン酸エステル類、ステアリン酸等の可塑剤が添加されていてもよい。
　前記紙としては、例えば、濾紙及び和紙が挙げられる。
　本発明の別の実施形態である組成物は、本発明化合物又は組成物Ａを、樹脂に担持させた組成物である。
　本発明のまた別の実施形態である組成物は、本発明化合物又は組成物Ａを、紙に担持させた組成物である。 The composition according to one embodiment of the present invention is a composition in which the compound of the present invention or composition A is supported on a resin or paper. Also, the preparation according to one embodiment of the present invention is a non-heated evaporative agent containing the composition.
Examples of the resin include polyethylene resins such as low-density polyethylene, linear low-density polyethylene, and high-density polyethylene; ethylene-vinyl ester copolymers such as ethylene-vinyl acetate copolymer; ethylene-methacrylic acid ester copolymers such as ethylene-methyl methacrylate copolymer and ethylene-ethyl methacrylate copolymer; ethylene-acrylic acid ester copolymers such as ethylene-methyl acrylate copolymer and ethylene-ethyl acrylate copolymer; ethylene-vinyl carboxylic acid copolymers such as ethylene-acrylic acid copolymer; ethylene-tetracyclododecene copolymer; polypropylene resins such as propylene polymers and propylene-ethylene copolymers; poly-4-methylpentene-1, polybutene-1, polybutadiene, polystyrene, and acrylonitrile-styrene resins; acrylonitrile-styrene resins such as ethylene-vinyl carboxylic acid copolymers; Examples of the resin include styrene-based elastomers such as styrene-conjugated diene copolymers and hydrogenated styrene-conjugated diene block copolymers; fluororesins; acrylic resins such as polymethyl methacrylate; polyamide resins such as nylon 6 and nylon 66; polyester resins such as polyethylene terephthalate, polyethylene naphthalate, polybutylene terephthalate, and polycyclohexylene dimethylene terephthalate; polycarbonate, polyacetal, polyacrylsulfone, polyarylate, hydroxybenzoic acid polyester, polyetherimide, polyester carbonate, polyphenylene ether resin, polyvinyl chloride, polyvinylidene chloride, and polyurethane. These resins may be used alone or in combination of two or more. If necessary, plasticizers such as phthalates (dimethyl phthalate, dioctyl phthalate, and the like), adipic acid esters, and stearic acid may be added to these resins.
Examples of the paper include filter paper and Japanese paper.
Another embodiment of the composition of the present invention is a composition in which the compound of the present invention or Composition A is supported on a resin.
A composition which is yet another embodiment of the present invention is a composition in which the compound of the present invention or composition A is supported on paper.
　以下、本発明を製造例、参考製造例、及び試験例等によりさらに詳しく説明するが、本発明はこれらの例のみに限定されるものではない。 The present invention will be explained in more detail below with reference to manufacturing examples, reference manufacturing examples, and test examples, but the present invention is not limited to these examples.
　まず、本発明化合物及びその製造中間体の製造例を示す。 First, we will show examples of the production of the compound of the present invention and its production intermediates.
参考製造例
　特開２００１－１１０２２号公報の製造例１に記載の方法で製造した４－メトキシメチル－２，３，５，６－テトラフルオロベンジル　３－（２－メチル－１－プロペニル）－２，２－ジメチルシクロプロパンカルボキシレート１．１１ｇ、クロロホルム１０ｍＬ及びメタノール１３２μＬの混合物に、氷冷下で四塩化チタン（１．０Ｍ　トルエン溶液）１．４８ｍＬを加え、室温で２４時間撹拌した。得られた混合物にメタノールを加えた後、セライト（登録商標）でろ過し、ろ液を減圧下で濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィー（ヘキサン：酢酸エチル＝１０：１）に付し、中間体１を１．０２ｇ得た。
Figure JPOXMLDOC01-appb-C000005
 中間体１：1H-NMR（CDCl3）δ：5.29-5.19 (2H, m), 4.59 (2H, s), 3.40 (3H, s), 1.92 (1H, dd), 1.79 (1H, dd), 1.62-1.57 (7H, m), 1.27 (1H, d), 1.25 (3H, s), 1.14 (3H, s). Reference Preparation Example: To a mixture of 1.11 g of 4-methoxymethyl-2,3,5,6-tetrafluorobenzyl 3-(2-methyl-1-propenyl)-2,2-dimethylcyclopropanecarboxylate prepared by the method described in Preparation Example 1 of JP-A-2001-11022, 10 mL of chloroform, and 132 μL of methanol, 1.48 mL of titanium tetrachloride (1.0 M toluene solution) was added under ice cooling, and the mixture was stirred at room temperature for 24 hours. Methanol was added to the resulting mixture, which was then filtered through Celite (registered trademark), and the filtrate was concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain 1.02 g of intermediate 1.
Figure JPOXMLDOC01-appb-C000005
 Intermediate 1: 1H -NMR ( CDCl3 ) δ: 5.29-5.19 (2H, m), 4.59 (2H, s), 3.40 (3H, s), 1.92 (1H, dd), 1.79 (1H, dd), 1.62-1.57 (7H, m), 1.27 (1H, d), 1.25 (3H, s), 1.14 (3H, s).
製造例
　０．３０ｇの中間体１、アセトン１０ｍＬ及び水２ｍＬの混合物に、酸化亜鉛０．０６ｇを加え、加熱還流下で１２時間撹拌した。得られた混合物に水を加えた後、セライト（登録商標）でろ過し、メチルｔｅｒｔ－ブチルエーテルで抽出した。得られた有機層を無水硫酸マグネシウムで乾燥し、減圧下で濃縮した。得られた残渣をシリカゲルカラムクロマトグラフィー（ヘキサン：酢酸エチル＝１０：１）に付し、本発明化合物を０．１０ｇ得た。 Production Example: 0.06 g of zinc oxide was added to a mixture of 0.30 g of intermediate 1, 10 mL of acetone, and 2 mL of water, and the mixture was stirred under heating and reflux for 12 hours. Water was added to the resulting mixture, which was then filtered through Celite (registered trademark) and extracted with methyl tert-butyl ether. The resulting organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain 0.10 g of the present compound.
　本発明化合物の1H-NMRデータを以下に示す。
本発明化合物：1H-NMR（CDCl3）δ：5.28-5.17 (2H, m), 4.59 (2H, s), 3.40 (3H, s), 1.62 (1H, dd), 1.54-1.43 (2H, ｍ), 1.30 (1H, s), 1.28-1.20 (10H, s), 1.13 (3H, s). The 1 H-NMR data of the compound of the present invention are shown below.
Compound of the present invention: 1H -NMR ( CDCl3 ) δ: 5.28-5.17 (2H, m), 4.59 (2H, s), 3.40 (3H, s), 1.62 (1H, dd), 1.54-1.43 (2H, m), 1.30 (1H, s), 1.28-1.20 (10H, s), 1.13 (3H, s).
　次に、本発明化合物の植物病害に対する効力を試験例により示す。 Next, the efficacy of the compound of the present invention against plant diseases will be shown by test examples.
試験例１
　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シリカの混合物（重量比１：１）３５重量部と、本発明化合物１０重量部と、水５５重量部とを混合し、湿式粉砕法で微粉砕し、製剤を得た。得られた製剤と水とを混合し、本発明化合物を１０００ｐｐｍ含有する混合物を得た。
　プラスチックポットに土壌を詰め、そこにイネ（品種；ヒノヒカリ）を播種し、温室内で２０日間栽培した。その後、得られた混合物を、上記イネの葉面に充分付着するように茎葉散布した。散布後、イネを風乾し、昼間２４℃、夜間２０℃多湿下で、前記散布処理をしたイネと、イネいもち病菌（Magnaporthe grisea）に罹病したイネ苗（品種；ヒノヒカリ）とを接触させながら６日間置いた後、病斑面積を調査した。
　本発明化合物を処理したイネにおける病斑面積は、無処理のイネにおける病斑面積の１０％以下であった。なお、無処理とは、本発明化合物を含有する混合物の散布を行わなかったことを意味する。 Test Example 1
35 parts by weight of a mixture of polyoxyethylene alkyl ether sulfate ammonium salt and silica (weight ratio 1:1), 10 parts by weight of the compound of the present invention, and 55 parts by weight of water were mixed and finely ground by a wet grinding method to obtain a preparation. The obtained preparation was mixed with water to obtain a mixture containing 1000 ppm of the compound of the present invention.
Plastic pots were filled with soil, rice (variety: Hinohikari) was sown therein, and cultivated in a greenhouse for 20 days. The mixture obtained was then sprayed on the stems and leaves of the rice so that it was sufficiently attached to the leaf surface of the rice. After spraying, the rice was air-dried, and the sprayed rice was placed in contact with rice seedlings (variety: Hinohikari) infected with rice blast fungus (Magnaporthe grisea) for 6 days under high humidity at 24°C during the day and 20°C at night, and the lesion area was then examined.
The lesion area in the rice treated with the compound of the present invention was 10% or less of that in the untreated rice, where "untreated" means that the mixture containing the compound of the present invention was not sprayed.
　本発明化合物は、植物病害に対して優れた防除効果を示す。 The compound of the present invention exhibits excellent control effects against plant diseases.

Claims (13)

  1. 　式（Ｉ）；
    Figure JPOXMLDOC01-appb-C000001
     で示される化合物。     Formula (I);
    Figure JPOXMLDOC01-appb-C000001
     A compound represented by the formula:
  2. 　請求項１に記載の化合物と、不活性担体とを含有する組成物。 A composition comprising the compound of claim 1 and an inert carrier.
  3. 　請求項１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。 A method for controlling plant diseases by applying an effective amount of the compound according to claim 1 to a plant or soil.
  4. 　請求項１に記載の化合物と、メトフルトリン及びジメフルトリンからなる群より選ばれる１以上の化合物とを含有する組成物。 A composition containing the compound according to claim 1 and one or more compounds selected from the group consisting of metofluthrin and dimefluthrin.
  5. 　請求項１に記載の化合物又は請求項４に記載の組成物と、水、アルコール類、ケトン類、芳香族炭化水素類、脂肪族炭化水素類、エステル類、ニトリル類、エーテル類、アミド類、ハロゲン化炭化水素類、スルホキシド類、鉱物油類、及び植物油類からなる群より選ばれる１以上の液体担体とを含有する組成物。 A composition comprising the compound according to claim 1 or the composition according to claim 4 and one or more liquid carriers selected from the group consisting of water, alcohols, ketones, aromatic hydrocarbons, aliphatic hydrocarbons, esters, nitriles, ethers, amides, halogenated hydrocarbons, sulfoxides, mineral oils, and vegetable oils.
  6. 　請求項１に記載の化合物又は請求項４に記載の組成物と、アルキル硫酸エステル塩、アルキルスルホン酸塩、アルキルアリールスルホン酸塩、アルキルアリールエーテル類、アルキルアリールエーテル類のポリオキシエチレン化物、ポリエチレングリコールエーテル類、多価アルコールエステル類、及び糖アルコール誘導体からなる群より選ばれる１以上の界面活性剤とを含有する組成物。 A composition comprising the compound according to claim 1 or the composition according to claim 4 and one or more surfactants selected from the group consisting of alkyl sulfate ester salts, alkyl sulfonate salts, alkylaryl sulfonate salts, alkylaryl ethers, polyoxyethylated alkylaryl ethers, polyethylene glycol ethers, polyhydric alcohol esters, and sugar alcohol derivatives.
  7. 　請求項１に記載の化合物又は請求項４に記載の組成物と、カゼイン、ゼラチン、多糖類、リグニン誘導体、ベントナイト、及び合成水溶性高分子からなる群より選ばれる１以上の増粘剤とを含有する組成物。 A composition comprising the compound according to claim 1 or the composition according to claim 4 and one or more thickeners selected from the group consisting of casein, gelatin, polysaccharides, lignin derivatives, bentonite, and synthetic water-soluble polymers.
  8. 　請求項１に記載の化合物又は請求項４に記載の組成物と、ＢＨＴ（２，６－ジ－ｔ－ブチル－４－メチルフェノール）、及びＢＨＡ（２－ｔ－ブチル－４－メトキシフェノールと３－ｔ－ブチル－４－メトキシフェノールとの混合物）からなる群より選ばれる１以上の酸化防止剤とを含有する組成物。 A composition containing the compound according to claim 1 or the composition according to claim 4 and one or more antioxidants selected from the group consisting of BHT (2,6-di-t-butyl-4-methylphenol) and BHA (a mixture of 2-t-butyl-4-methoxyphenol and 3-t-butyl-4-methoxyphenol).
  9. 　請求項１に記載の化合物又は請求項４に記載の組成物を、植物性粉末に担持させた組成物。 A composition in which the compound described in claim 1 or the composition described in claim 4 is supported on a plant powder.
  10. 　請求項１に記載の化合物又は請求項４に記載の組成物と、結合剤とを含有する組成物。 A composition comprising the compound according to claim 1 or the composition according to claim 4 and a binder.
  11. 　請求項１に記載の化合物又は請求項４に記載の組成物を、コットンリンター及びパルプからなる群より選ばれる１以上の基材に担持させた組成物。 A composition in which the compound according to claim 1 or the composition according to claim 4 is supported on one or more substrates selected from the group consisting of cotton linters and pulp.
  12. 　請求項１に記載の化合物又は請求項４に記載の組成物を、熱可塑性樹脂、又は紙に担持させた組成物。 A composition in which the compound according to claim 1 or the composition according to claim 4 is supported on a thermoplastic resin or paper.
  13. 　請求項４～１２のいずれか１項に記載の組成物を含有する、油剤、乳剤、フロアブル剤、エアゾール剤、加熱蒸散剤、非加熱蒸散剤、煙霧剤、及びＵＬＶ剤からなる群より選ばれる製剤。 A preparation selected from the group consisting of an oil solution, an emulsion, a flowable agent, an aerosol agent, a heated evaporation agent, a non-heated evaporation agent, a fog agent, and an ULV agent, which contains the composition according to any one of claims 4 to 12.
PCT/JP2023/044005 2023-02-20 2023-12-08 Cyclopropanecarboxylic acid ester compound and use thereof WO2024071440A1 (en)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5746940A (en) * 1980-09-04 1982-03-17 Mitsubishi Chem Ind Ltd Cyclopropanecarboxylic acid ester
JP2001011022A (en) * 1998-11-20 2001-01-16 Sumitomo Chem Co Ltd Pyrethroid compound and pest controller containing the same as active ingredient
JP2004315506A (en) * 2003-03-31 2004-11-11 Sumitomo Chem Co Ltd Method for producing carbonyl compound

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5746940A (en) * 1980-09-04 1982-03-17 Mitsubishi Chem Ind Ltd Cyclopropanecarboxylic acid ester
JP2001011022A (en) * 1998-11-20 2001-01-16 Sumitomo Chem Co Ltd Pyrethroid compound and pest controller containing the same as active ingredient
JP2004315506A (en) * 2003-03-31 2004-11-11 Sumitomo Chem Co Ltd Method for producing carbonyl compound

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