WO2024070892A1 - Composé d'ester d'acide cyclopropanecarboxylique et son utilisation - Google Patents

Composé d'ester d'acide cyclopropanecarboxylique et son utilisation Download PDF

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Publication number
WO2024070892A1
WO2024070892A1 PCT/JP2023/034321 JP2023034321W WO2024070892A1 WO 2024070892 A1 WO2024070892 A1 WO 2024070892A1 JP 2023034321 W JP2023034321 W JP 2023034321W WO 2024070892 A1 WO2024070892 A1 WO 2024070892A1
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Prior art keywords
composition
compound
compound according
group
diseases
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PCT/JP2023/034321
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English (en)
Japanese (ja)
Inventor
康 片桐
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住友化学株式会社
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Publication of WO2024070892A1 publication Critical patent/WO2024070892A1/fr

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • 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
    • 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

Definitions

  • the present invention relates to cyclopropane carboxylate compounds and their uses.
  • Patent Document 1 lists a compound represented by the formula (A) as having excellent efficacy for home quarantine use.
  • 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 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 sulfate salts, alkyl sulfonate salts, alkylaryl sulfonate salts, 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, synthetic water-soluble polymers, and polyacrylic acid.
  • a composition comprising 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).
  • 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.
  • a composition comprising the compound according to [1] or the composition according to [4] and a binder.
  • 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.
  • 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 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 usually contains 0.0001 to 95% by weight of the compound of the present invention.
  • 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 ethers, polyoxyethylene alkylaryl ethers, and polyethylene glycol fatty acid esters, and anionic surfactants such as alkyl sulfonates, alkylbenzene sulfonates, and alkyl sulfates.
  • nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, and polyethylene glycol fatty acid esters
  • anionic surfactants such as alkyl sulfonates, alkylbenzene 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, 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, 2,6-di
  • 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), 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),
  • 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.
  • the compound of the present invention is formulated as an emulsifiable concentrate, wettable powder, flowable powder or the like, it is usually applied after diluting with water so that the active ingredient concentration becomes 0.01 to 10,000 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.
  • the compound of the present invention is represented by the formula (I'): It is preferable to use an optically active substance represented by the formula: or a mixture of isomers rich in said optically active substance.
  • 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, but 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, , 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, 1:50, and the like.
  • 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 striated brown planthopper, brown planthopper, and white-backed planthopper; leafhoppers such as the green rice leafhopper and the Taiwan 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; white butterflies such as the cabbage white butterfly; tortrix moths such as the small tortrix moth; fruit borers, leafminers, tussock moths, grasshoppers, Agrotis spp. such as the turnip cutworm and the rice cutworm; Helicoverpa pests Heliothis spp.), diamondback moth, skipper butterfly, burr moth, Japanese moth, etc.
  • Diptera pests Culex pipiens quinquefasciatus and Culex tritaeniorhynchus, Aedes aegypti and Aedes albopictus, Anopheles sinensis and Anopheles sinensis, chironomids, houseflies and Musca domestica and Musca domestica, blowflies, flesh flies, seed flies, little house flies, onion flies and other flower flies, fruit flies, Drosophila melanogaster, horseflies, black flies, stable flies, etc.
  • Coleoptera pests corn rootworms such as the western corn rootworm and the southern corn rootworm; scarab beetles such as the cupreous beetle and the dung beetle; weevils such as the rice weevil, rice water weevil, boll weevil, and azuki bean weevil; meal beetles such as the brown meal beetle and the red flour beetle; leaf beetles such as the rice leaf beetle, the yellow flea beetle, and the cucumber beetle; beetles, Epilachna spp.
  • Dictyoptera pests German cockroach, brown cockroach, American cockroach, brown cockroach, and oriental cockroach.
  • Thysanoptera pests Thrips palmi, thrips citri, flower thrips, etc.
  • Hymenoptera pests Ants, wasps, ant wasps, sawflies such as turnip sawflies, etc.
  • Orthoptera pests mole crickets, grasshoppers, etc.
  • Crypoptera pests human fleas, cat fleas, etc.
  • Phthiraptera pests human lice, pubic lice, etc. Ectoptera pests: Japanese termite, Formosan termite, etc.
  • Indoor dust mites Dermatophagoides farinae, Dermatophagoides pteronyssinus, and other dust mites; grain mites, such as Tyrophagus putrescentiae and Acarus vicina; flesh mites, such as Dermestida dust mites, Glycine max householdi, and Dermestida gracilis; chigger mites, such as Cheyletiella stag beetle and Cheyletiella plicata; dust mites, Sarcoptes orbiculatus, house mites, spider mites, ixodid mites, such as Haemaphysalis longicornis; two-spotted spider mites, Kanzawa spider mites, citrus red mite, brown mite, etc. Harmful arthropods may be those which have reduced
  • 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 which is one embodiment of the present invention is a formulation containing the compound of the present invention or Composition A, and 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 an 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.
  • 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 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 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 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, 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 500 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.

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Zoology (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Environmental Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Dentistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention concerne un composé ayant une excellente efficacité de lutte contre les maladies des plantes. Un composé représenté par la formule (I) présente une excellente efficacité de lutte contre les maladies des plantes.
PCT/JP2023/034321 2022-09-26 2023-09-21 Composé d'ester d'acide cyclopropanecarboxylique et son utilisation WO2024070892A1 (fr)

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JP2022-152272 2022-09-26
JP2022152272 2022-09-26

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06316569A (ja) * 1992-08-10 1994-11-15 Dainippon Jochugiku Co Ltd 新規カルボン酸エステル誘導体、およびこれを含有する 殺虫、殺ダニ剤
JP2001011022A (ja) * 1998-11-20 2001-01-16 Sumitomo Chem Co Ltd ピレスロイド化合物およびそれを有効成分として含有する有害生物防除剤
JP2018500361A (ja) * 2014-12-30 2018-01-11 ダウ アグロサイエンシィズ エルエルシー 殺真菌剤としてのピコリンアミドの使用
JP2020066621A (ja) * 2018-10-23 2020-04-30 住友化学株式会社 エステル化合物及びその用途

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06316569A (ja) * 1992-08-10 1994-11-15 Dainippon Jochugiku Co Ltd 新規カルボン酸エステル誘導体、およびこれを含有する 殺虫、殺ダニ剤
JP2001011022A (ja) * 1998-11-20 2001-01-16 Sumitomo Chem Co Ltd ピレスロイド化合物およびそれを有効成分として含有する有害生物防除剤
JP2018500361A (ja) * 2014-12-30 2018-01-11 ダウ アグロサイエンシィズ エルエルシー 殺真菌剤としてのピコリンアミドの使用
JP2020066621A (ja) * 2018-10-23 2020-04-30 住友化学株式会社 エステル化合物及びその用途

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