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WO2015178262A1 - Composé pyrazole - Google Patents

Composé pyrazole Download PDF

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Publication number
WO2015178262A1
WO2015178262A1 PCT/JP2015/063726 JP2015063726W WO2015178262A1 WO 2015178262 A1 WO2015178262 A1 WO 2015178262A1 JP 2015063726 W JP2015063726 W JP 2015063726W WO 2015178262 A1 WO2015178262 A1 WO 2015178262A1
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WO
WIPO (PCT)
Prior art keywords
compound
present
reaction
methyl
acid
Prior art date
Application number
PCT/JP2015/063726
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English (en)
Japanese (ja)
Inventor
英樹 采女
康 片桐
Original Assignee
住友化学株式会社
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
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Publication of WO2015178262A1 publication Critical patent/WO2015178262A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D231/18—One oxygen or sulfur atom
    • C07D231/20—One oxygen atom attached in position 3 or 5

Definitions

  • the present invention relates to a pyrazole compound and its use for controlling harmful arthropods.
  • An object of the present invention is to provide a novel compound having a controlling activity against harmful arthropods.
  • the present invention is as follows.
  • Formula (1) A pyrazole compound represented by the following (hereinafter referred to as the present compound).
  • a harmful arthropod control agent comprising a pyrazole compound represented by the formula (1) and an inert carrier.
  • a method for controlling harmful arthropods which comprises applying an effective amount of a pyrazole compound represented by the formula (1) to harmful arthropods or a place where the harmful arthropods grow.
  • Me represents a methyl group.
  • examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • the leaving group represents a halogen atom, an alkylsulfonyloxy group or an arylsulfonyloxy group, for example, a fluorine atom, a chlorine atom, a bromine atom or an iodine atom, a methanesulfonyloxy group, trifluoromethanesulfonyl
  • alkylsulfonyloxy groups such as oxy group
  • arylsulfonyloxy groups such as benzenesulfonyloxy group and p-toluenesulfonyloxy group.
  • the compounds of the present invention include geometric isomers derived from carbon-nitrogen double bonds present in the oxime moiety, and the present invention includes each of these and mixtures thereof.
  • Examples of the present compound include the following pyrazole compounds.
  • a pyrazole compound in which the geometric isomer derived from the double bond present in the oxime moiety is E-form in formula (1);
  • a pyrazole compound in which the geometric isomer derived from a double bond present in the oxime moiety is a Z-form;
  • the compound of the present invention can be produced by reacting compound (2) with compound (3).
  • X 1 represents a leaving group.
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include water; alcohols such as methanol, ethanol and isopropyl alcohol; ketones such as acetone and methyl ethyl ketone; tetrahydrofuran (hereinafter sometimes referred to as THF), diethyl ether, tert-butyl methyl ether, and ethylene.
  • Ethers such as glycol dimethyl ether and 1,4-dioxane; acid amides such as N, N-dimethylformamide (hereinafter sometimes referred to as DMF); nitriles such as acetonitrile; aromatic hydrocarbons such as toluene and xylene; pentane; Aliphatic hydrocarbons such as hexane and heptane; esters such as ethyl acetate; sulfoxides such as dimethyl sulfoxide; sulfolanes; halogenated hydrocarbons such as 1,2-dichloroethane, chloroform and chlorobenzene, and mixtures thereof It is done.
  • DMF N, N-dimethylformamide
  • the amount of compound (3) to be used is generally 0.5 to 5 mol per 1 mol of compound (2).
  • the reaction is usually performed in the presence of a base.
  • the base used in the reaction include alkali metal hydrides such as sodium hydride; carbonates such as sodium carbonate, potassium carbonate and cesium carbonate; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; potassium tert- And alkali metal alkoxides such as butoxide and organic amines such as triethylamine, pyridine, 1,8-diazabicyclo [5.4.0] undec-7-ene).
  • the amount of the base to be used is generally 1 to 5 mol per 1 mol of compound (2).
  • the reaction may be carried out in the presence of a phase transfer catalyst.
  • the phase transfer catalyst include quaternary ammonium salts such as tetrabutylammonium bromide and benzyltriethylammonium chloride.
  • the amount of the phase transfer catalyst to be used is generally 0.01-0.5 mol per 1 mol of compound (2).
  • the reaction temperature is usually in the range of 0 to 100 ° C., and the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound of the present invention can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, drying and concentration.
  • the isolated compound of the present invention can be further purified by chromatography, recrystallization and the like.
  • the compound of the present invention can also be produced by reacting compound (4) with compound (5).
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include alcohols such as methanol, ethanol and isopropyl alcohol; ethers such as tetrahydrofuran, diethyl ether, tert-butyl methyl ether, ethylene glycol dimethyl ether and 1,4-dioxane; N, N-dimethylformamide and the like.
  • Acid amides such as acetonitrile; aromatic hydrocarbons such as toluene and xylene; aliphatic hydrocarbons such as pentane, hexane and heptane; esters such as ethyl acetate; sulfoxides such as dimethyl sulfoxide; sulfolane; 1,2-dichloroethane , Halogenated hydrocarbons such as chloroform and chlorobenzene; carboxylic acids such as acetic acid and mixtures thereof.
  • Compound (5) may be compound (5) itself or a salt of compound (5) and an acid. Examples of the acid include hydrochloric acid, sulfuric acid, phosphoric acid and the like.
  • the amount of compound (5) to be used is generally 1 to 5 mol per 1 mol of compound (4).
  • the reaction may be performed in the presence of an acid.
  • the acid include acetic acid, hydrochloric acid, sulfuric acid, phosphoric acid and the like.
  • the amount of the acid to be used is generally 0.01 mol-10 mol per 1 mol of compound (4).
  • the reaction may be performed in the presence of a base.
  • the base include triethylamine, pyridine, sodium hydrogen carbonate, sodium carbonate, potassium carbonate, sodium hydroxide, potassium hydroxide and the like.
  • the amount of the base to be used is generally 0.01 mol-10 mol per 1 mol of compound (4).
  • the reaction may be carried out under conditions where molecular sieves, anhydrous sodium chloride, anhydrous sodium sulfate, etc. are usually present in an amount of 1 to 10 grams per 1 gram of compound (4).
  • the reaction temperature is usually in the range of 0 to 100 ° C.
  • the reaction time is usually in the range of 0.5 to 24 hours.
  • the compound of the present invention can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, drying and concentration.
  • the isolated compound of the present invention can be further purified by chromatography, recrystallization and the like.
  • the compound of the present invention can also be produced by reacting compound (6) with compound (7).
  • X 2 represents a leaving group.
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include water; alcohols such as methanol, ethanol and isopropyl alcohol; ketones such as acetone and methyl ethyl ketone; tetrahydrofuran, diethyl ether, tert-butyl methyl ether, ethylene glycol dimethyl ether, 1,4-dioxane and the like.
  • Ethers acid amides such as N, N-dimethylformamide; nitriles such as acetonitrile; aromatic hydrocarbons such as toluene and xylene; aliphatic hydrocarbons such as pentane, hexane and heptane; esters such as ethyl acetate; dimethyl sulfoxide and the like Examples thereof include sulfoxides; sulfolanes; halogenated hydrocarbons such as 1,2-dichloroethane, chloroform and chlorobenzene, and mixtures thereof.
  • the amount of compound (7) to be used is generally 0.5 to 5 mol per 1 mol of compound (6).
  • the reaction is usually performed in the presence of a base.
  • Examples of the base used in the reaction include alkali metal hydrides such as sodium hydride; carbonates such as sodium carbonate, potassium carbonate and cesium carbonate; alkali metal hydroxides such as sodium hydroxide and potassium hydroxide; potassium tert- And alkali metal alkoxides such as butoxide and organic amines such as triethylamine, pyridine, 1,8-diazabicyclo [5.4.0] undec-7-ene).
  • the amount of the base to be used is generally 1 to 5 mol per 1 mol of compound (6).
  • the reaction may be carried out in the presence of a phase transfer catalyst.
  • phase transfer catalyst examples include quaternary ammonium salts such as tetrabutylammonium bromide and benzyltriethylammonium chloride.
  • the amount of the phase transfer catalyst to be used is generally 0.01-0.5 mol per 1 mol of compound (6).
  • the reaction temperature is usually in the range of 0 to 100 ° C., and the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound of the present invention can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, drying and concentration.
  • the isolated compound of the present invention can be further purified by chromatography, recrystallization and the like.
  • Compound (2) can be produced by reacting compound (4) with hydroxylamine. The reaction is carried out according to (Production Method 2).
  • the compound (3 ′) in which X 1 is a chlorine atom or a bromine atom is produced by reacting the compound (9) with thionyl chloride or thionyl bromide represented by the compound (10).
  • X 1 ′ represents a chlorine atom or a bromine atom.
  • the reaction is usually performed in a solvent.
  • Solvents used for the reaction include ethers such as tetrahydrofuran, diethyl ether, tert-butyl methyl ether, ethylene glycol dimethyl ether, and 1,4-dioxane; aromatic hydrocarbons such as toluene and xylene; fats such as pentane, hexane, and heptane Group hydrocarbons; esters such as ethyl acetate; halogenated hydrocarbons such as 1,2-dichloroethane, chloroform and chlorobenzene, and mixtures thereof.
  • the amount of compound (10) to be used is generally 1 to 5 mol per 1 mol of compound (9).
  • the reaction may be performed in the presence of organic amines.
  • organic amines examples include triethylamine and pyridine.
  • the amount of the base to be used is generally 1 to 5 mol per 1 mol of compound (9).
  • the reaction temperature is usually in the range of 0 to 100 ° C., and the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound of the present invention can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, drying and concentration.
  • the isolated compound (3 ′ ) can be further purified by chromatography, recrystallization and the like.
  • Solvents used for the reaction include ethers such as tetrahydrofuran, diethyl ether, tert-butyl methyl ether, ethylene glycol dimethyl ether, and 1,4-dioxane; aromatic hydrocarbons such as toluene and xylene; fats such as pentane, hexane, and heptane Group hydrocarbons; esters such as ethyl acetate; halogenated hydrocarbons such as 1,2-dichloroethane, chloroform and chlorobenzene, and mixtures thereof.
  • the amount of compound (11) to be used is generally 1 to 5 mol per 1 mol of compound (9).
  • the amount of triphenylphosphine to be used is generally 1 to 5 mol per 1 mol of compound (9).
  • the reaction temperature is usually in the range of 0 to 100 ° C., and the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound of the present invention can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, drying and concentration.
  • the isolated compound (3 ′ ) can be further purified by chromatography, recrystallization and the like.
  • Compound (5) can be produced by reacting compound (13) with hydrazine monohydrate.
  • the reaction is usually performed in a solvent.
  • the solvent used for the reaction include alcohols such as methanol, ethanol and isopropyl alcohol.
  • the amount of hydrazine monohydrate to be used is generally 1 to 5 mol per 1 mol of compound (13).
  • the reaction temperature is usually in the range of 50 to 100 ° C., and the reaction time is usually in the range of 0.5 to 24 hours.
  • the compound of the present invention can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, drying and concentration.
  • the isolated compound (5) can be further purified by chromatography, recrystallization and the like.
  • Compound (13) can be produced by reacting compound (9) with compound (14) in the presence of triphenylphosphine and diethyl azodicarboxylate.
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include ethers such as tetrahydrofuran, diethyl ether, tert-butyl methyl ether, ethylene glycol dimethyl ether, and 1,4-dioxane; aromatic hydrocarbons such as toluene and xylene, pentane, hexane, and heptane.
  • Aliphatic hydrocarbons such as 1,2-dichloroethane, chloroform, chlorobenzene and mixtures thereof.
  • the amount of compound (14) to be used is generally 0.5 to 2 mol per 1 mol of compound (9).
  • the amount of triphenylphosphine to be used is generally 0.5-2 mol per 1 mol of compound (9).
  • the amount of diethyl azodicarboxylate to be used is generally 0.5-2 mol per 1 mol of compound (9).
  • the reaction temperature is usually in the range of 0 to 50 ° C., and the reaction time is usually in the range of 0.5 to 24 hours.
  • the compound of the present invention can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, drying and concentration.
  • the isolated compound (13) can be further purified by chromatography, recrystallization and the like.
  • Compound (13) can also be produced by reacting compound (3) with compound (14). [Wherein, X 1 represents a leaving group. ] The reaction is carried out according to (Production Method 1).
  • Compound (6) can be produced by reacting compound (8) with compound (3). [Wherein, X 1 and X 2 represent a leaving group. ] The reaction is carried out according to (Production Method 1).
  • Compound (6) can be produced by reacting compound (12) with compound (5). [Wherein, X 2 represents a leaving group. ] The reaction is carried out according to (Production Method 2).
  • the compound (3 ′′) in which X 1 is a chlorine atom, bromine atom or iodine atom is hydrogen chloride, hydrogen bromide or iodine represented by the compound (9) and the compound (15). It can be produced by reacting with hydrogen fluoride.
  • X 1 ′′ represents a chlorine atom, a bromine atom or an iodine atom.
  • the reaction is usually carried out in the corresponding hydrogen halide water (that is, hydrochloric acid, hydrogen bromide water, hydrogen iodide water), but a solvent inert to the reaction may be mixed.
  • Examples of the solvent inert to the reaction include ethers such as diethyl ether, tert-butyl methyl ether, and ethylene glycol dimethyl ether; aromatic hydrocarbons such as toluene and xylene; aliphatic hydrocarbons such as pentane, hexane, and heptane; -Halogenated hydrocarbons such as dichloroethane, chloroform, chlorobenzene and mixtures thereof.
  • the amount of compound (15) to be used is generally 2 to 20 mol per 1 mol of compound (9).
  • the reaction temperature is usually in the range of 0 to 100 ° C., and the reaction time is usually in the range of 0.1 to 24 hours.
  • the compound of the present invention can be isolated by performing post-treatment operations such as extraction of the reaction mixture with an organic solvent, drying and concentration.
  • the isolated compound (3 ′′) can be further purified by chromatography, recrystallization and the like.
  • compound (7), compound (8), compound (9), compound (10), compound (11), compound (12), compound (14) and compound (15) are publicly known. Or can be produced from a known compound according to a known method.
  • harmful arthropods for which the compounds of the present invention are effective include harmful insects and harmful mites. More specifically, the following are mentioned.
  • Hemiptera small brown planthopper (Laodelphax striatella), brown planthopper (Nilaparvata lugens), planthoppers such as Sejirounka (Sogatella furcifera), green rice leafhopper (Nephotettix cincticeps), Taiwan green rice leafhopper (Nephotettix virescens), tea Roh green leafhopper (Empoasca onukii) such as Leafhoppers, cotton aphids (Aphis gossypii), peach aphids (Myzus persicae), radish aphids (Brevicorine brassicae), aphid spiraecola, tulip beetle aphids Macrosiphum euphorbiae, potato beetle aphids (Aulacorthum solani), wheat beetle aphids (Rhopalosiphum aphids), citrus aphid
  • Lepidoptera rice stem borer (Chilo suppressalis), Sankameiga (Tryporyza incertulas), leaf roller (Cnaphalocrocis medinalis), Watanomeiga (Notarcha derogata), Indian meal moth (Plodia interpunctella), the European corn borer (Ostrinia furnacalis), high Madara Roh moth (Hellula undalis), Common moths such as Shibatatsuga (Pediasia teterrellus), Lotus moth (Spodoptera litura), Spodoptera exigua, Ayuyotoga (Pseudaletia separata), Yotoga Mestra brassicae), Agrotis ipsilon, Tamanaginuwaba (Plusia nigrisigna), Trichopulcia, Heliotis, Helicoberpa, etc.
  • Species of the genus Cypridae such as Archopus fuscocuppreanus, Cydia pomonella, Chaptolia sapiens , Limantria genus, Euproctinis genus, etc., Pterella xylostella, etc., Suga, Peptinophora gossypiella potato moth (Phthorimaea operculella), etc.
  • a triggers such as a cunea, and Hirokosu koga such as iga (Tinea translucens) and koiga (Tineola bisselliella).
  • Culex Culex pipiens pallens
  • Culex Culex tritaeniorhynchus
  • Culex quinquefasciatus Culex quinquefasciatus
  • Culex such as, Aedes aegypti (Aedes aegypti), Aedes spp such as Aedes albopictus (Aedes albopictus), Anopheles sinensis (Anopheles sinensis), Anopheles genus such as Anopheles gambiae, chironomids, houseflies (Musca domestica), house flies such as Muscina stabulans, fly flies, sand flies, moth flies, i Delia antiqua) Anthomyiidae such as, rice leafminer (Agromyza oryzae), rice Hime leafminer (Hydrellia griseola),
  • Coleoptera pests Western Corn Rootworm (Diabrotica virgifera virgifera), corn rootworm such as southern corn rootworm (Diabrotica undecimpunctata howardi), cupreous chafer (Anomala cuprea), rufocuprea (Anomala rufocuprea), chafers such as Japanese beetle (Popillia japonica) , Weevil (Sitophilus zeamais), Rice weevil (Lissohoptrus oryzophilus), Azuki beetle (Callosobruchuys Kunststoffsis), Ezonocnemus squamus Weevil (Anthonomus grandis), Weevil weevil (Sphenophorus venatus) and other weevil, Tenebrio molitor, Aureum oleume olium (Olymoidum) Chestnut beetles (Phyllotreta striola), Colorado potato beetle (Leptinotarsa
  • Pterodoptera Tocusama grasshopper (Locusta migratoria), Kera (Gryllotalpa africana), Oxya yezoensis, Lobster (Oxya japonica) and crickets.
  • Insect pests cat fleas (Ctenocephalides felis), dog fleas (Ctenocephalides canis), human fleas (Pulex irritans), keops mud mines (Xenopsylla cheopes) and the like.
  • Anoplura body louse (Pediculus humanus corporis), head lice (Pediculus humanus humanus), crab louse (Phthirus pubis), Ushijirami (Haematopinus eurysternus), Hitsujijirami (Dalmalinia ovis), Butajirami (Haematopinus suis), Inujirami (Linognathus setosus) and the like.
  • ⁇ Lepidoptera sheep lice (Dalmalinia ovis), cattle lice (Dalmalinia bovis), chicken lice (Menopon gallinae), dog lice (Trichodictes canis), cat flies, etc.
  • Hymenoptera Monomorium phalaosis, Black sea ants (Formica fusca japonica), Luriari (Ochtellus puns), Pstomyrex puns, Pseudorme spr. Ants such as Argentine ants (Linepithema humile), wasps such as wasps, scallops, and wasps such as wasp (Athalia rosae) and Japanese bee (Athalia japonica).
  • Cockroach eye pests German cockroach (Blatella germanica), Black cockroach (Periplaneta fuliginosa), American cockroach (Periplaneta americana), Japanese cockroach (Peripraneta bruna)
  • Termite pests Reticulites speratus, Termite terminator (Coptoptermes formosanus), American termite terminus (Incitermes minors), Cyptotermes domesticus, Owantosistorus Glypoptermes satsumensis, Glyptotermes nakajimai, Caterpillars (Glypoptermes fuscus), Gyptotermes kodamai, Shimotoshiroari (Glyptotermes kushimensis), giant termite (Hodotermopsis japonica), Kou Shu Ye termite (Coptotermes guangzhoensis), Amami termites (Reticulitermes miyatakei), R.
  • Mite order pests Tick spider mites (Tetranychus urticae), Tick spider mites (Tetranychus kanzawai), citrus spider mite (Pananychus citri), mite spider mite (Panthonychus ulmi), prickly mite pistols, citrus urticae Tomato rust mites (Aculops lycopersici), Chanosabi mites (Calacarus carinatus), Chanogasabi mite (Acaphylla theevagrans), Green rust mites (Eriophyses chibaensis), Apple scab mites Achulus schizus endali) Fushidani such as, dust mite such as Chanohokoridani (Polyphagotarsonemus latus), southern Hime Himehadani such as spider mites (Brevipalpus phoenicis), Kenagahadani such, longicornis (Haemaphysalis longicornis), Yama
  • Lip limb class Geese (Thereunema hilgendorfi), Tobizukade (Scorpendra subspinipes), etc.
  • Double-legged class Oxidus gracilis, Nadeyopus tambanus, etc.
  • Isopods Armadillium vulgare, etc.
  • Gastropods Limax marginatus, Limax flavus, etc.
  • the harmful arthropod control agent of the present invention contains the compound of the present invention and an inert carrier.
  • the inert carrier represents a bulking agent, a diluent and the like used in the field of prevention and agriculture.
  • the harmful arthropod control agent of the present invention is usually a mixture of the compound of the present invention and an inert carrier such as a solid carrier, a liquid carrier, a gaseous carrier, etc., and if necessary, a surfactant and other adjuvants for formulation.
  • the harmful arthropod control agent of the present invention usually contains 0.01 to 95% by weight of the compound of the present invention.
  • solid carriers used for formulation include clays (kaolin clay, diatomaceous earth, bentonite, fusami clay, acidic clay), synthetic hydrous silicon oxide, talc, ceramics, and other inorganic minerals (sericite, quartz, sulfur).
  • Activated carbon calcium carbonate, hydrated silica, etc.
  • fine powders and granules of chemical fertilizers (ammonium sulfate, phosphorous, ammonium nitrate, urea, ammonium chloride, etc.), and synthetic resins (polyethylene, polypropylene, polyacrylonitrile, polymethacrylic)
  • Polyester resins such as methyl acid and polyethylene terephthalate, nylon resins such as nylon-6, nylon-11, and nylon-66, polyamide resins, polyvinyl chloride, polyvinylidene chloride, and vinyl chloride-propylene copolymers).
  • liquid carrier examples include water, alcohols (methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, phenoxyethanol, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, etc.), aromatic hydrocarbons (Toluene, xylene, ethylbenzene, dodecylbenzene, phenylxylylethane, methylnaphthalene, etc.), aliphatic hydrocarbons (hexane, cyclohexane, kerosene, light oil, etc.), esters (ethyl acetate, butyl acetate, isopropyl myristate, Ethyl oleate, diisopropyl adipate, diisobutyl adipate, propylene glycol monomethyl ether acetate, etc.), n
  • Acid amides N, N-dimethylformamide, N, N-dimethylacetamide, etc.
  • halogenated hydrocarbons diichloromethane, trichloroethane, carbon tetrachloride, etc.
  • sulfoxides dimethylsulfoxide, etc.
  • propylene carbonate and vegetable oil Soybean oil, cottonseed oil, etc.
  • gaseous carrier examples include fluorocarbon, butane gas, LPG (liquefied petroleum gas), dimethyl ether, and carbon dioxide gas.
  • surfactant examples include nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, and polyethylene glycol fatty acid ester, and anions such as alkyl sulfonate, alkyl benzene sulfonate, and alkyl sulfate. Surfactant is mentioned.
  • adjuvants for preparation include fixing agents, dispersants, colorants and stabilizers, such as casein, gelatin, saccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, Synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), PAP (isopropyl acid phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (2-tert- And a mixture of butyl-4-methoxyphenol and 3-tert-butyl-4-methoxyphenol).
  • fixing agents such as casein, gelatin, saccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, Synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), PAP (is
  • the base material of the resin preparation examples include vinyl chloride polymers, polyurethanes, etc., and these base materials include phthalic acid esters (dimethyl phthalate, dioctyl phthalate, etc.) and adipic acid esters as necessary. Further, a plasticizer such as stearic acid may be added.
  • the resin formulation is obtained by kneading the compound in the base material using a normal kneading apparatus, and then molding by injection molding, extrusion molding, press molding, etc., and if necessary, through steps such as molding, cutting, It can be processed into resin preparations such as plate, film, tape, net, and string.
  • These resin preparations are processed, for example, as animal collars, animal ear tags, sheet preparations, attracting strings, or gardening supports.
  • the bait base include cereal flour, vegetable oil, sugar, crystalline cellulose and the like, and if necessary, antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid, and preservatives such as dehydroacetic acid.
  • antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid
  • preservatives such as dehydroacetic acid.
  • Additives for preventing accidental eating by children and pets such as pepper powder, pests such as cheese flavor, onion flavor and peanut oil are added.
  • the harmful arthropod can be controlled by applying the harmful arthropod control agent of the present invention directly to the harmful arthropod and / or in the place where the harmful arthropod lives.
  • an effective amount of the compound of the present invention is applied directly to harmful arthropods and / or to the place where the harmful arthropods live (plants, soil, households, animal bodies, etc.). Is done.
  • the harmful arthropod control method of the present invention is usually used in the form of the harmful arthropod control agent of the present invention.
  • the application amount is usually 1 to 10,000 g in the amount of the compound of the present invention per 10,000 m 2 .
  • the harmful arthropod control agent of the present invention is formulated into an emulsion, a wettable powder, a flowable agent, etc., it is usually applied by diluting with water so that the active ingredient concentration becomes 0.01 to 10,000 ppm. Granules, powders and the like are usually applied as they are.
  • These preparations and water dilutions of these preparations may be sprayed directly on harmful arthropods or plants such as crops to be protected from harmful arthropods, and harmful arthropods that inhabit the soil of cultivated land. You may treat to this soil in order to control.
  • it can be treated by methods such as wrapping a resin preparation processed into a sheet or string around the crop, stretching it around the crop, or laying it on the stock soil.
  • the amount applied is usually the amount of the compound of the present invention per 1 m 2 when treated on the surface. 0.01 to 1000 mg, and when processing in a space, the amount of the compound of the present invention per 1 m 3 of the processing space is usually 0.01 to 500 mg.
  • the harmful arthropod control agent of the present invention is formulated into an emulsion, a wettable powder, a flowable agent, etc., it is usually diluted with water so that the active ingredient concentration is 0.1 to 10,000 ppm. Apply oils, aerosols, smoke, poison baits, etc. as they are.
  • the harmful arthropod control agent of the present invention When used to control ectoparasites of cattle, horses, pigs, sheep, goats, chickens, small animals such as dogs, cats, rats, mice, etc., it is well known in veterinary medicine. Can be used on animals.
  • systemic suppression for example, administration by tablet, feed mixing, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.) is intended for non-systemic suppression.
  • an oil agent or an aqueous liquid is sprayed, a pour-on treatment or a spot-on treatment is performed, the animal is washed with a shampoo preparation, or a resin preparation is attached to the animal with a collar or ear tag.
  • the amount of the compound of the present invention when administered to an animal body is usually in the range of 0.1 to 1000 mg per 1 kg body weight of the animal.
  • the harmful arthropod control agent of the present invention can be used in farmland where the following crops are cultivated.
  • Agricultural crops corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, buckwheat, sugar beet, rapeseed, sunflower, sugarcane, tobacco, etc.
  • Vegetables Solanum vegetables (eggplants, tomatoes, peppers, peppers, potatoes, etc.), Cucurbitaceae vegetables (cucumbers, pumpkins, zucchini, watermelons, melons, etc.), Brassicaceae vegetables (radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage) , Mustard, broccoli, cauliflower, etc.), asteraceae vegetables (burdock, shungiku, artichokes, lettuce, etc.), liliaceae vegetables (leek, onion, garlic, asparagus), celery family vegetables (carrot, parsley, celery, American scallop, etc.) ), Red crustacean vegetables (spinach, chard, etc.), persimmon vegetables (perilla, mint, basil, etc.), strawberry, sweet potato, yam, taro, etc.
  • Fruit trees berries (apples, pears, Japanese pears, quince, quince, etc.), nuclear fruits (peaches, plums, nectarines, ume, sweet cherry, apricots, prunes, etc.), citrus (satsuma mandarin, orange, lemon, lime, grapefruit) ), Nuts (chestnut, walnut, hazel, almond, pistachio, cashew nut, macadamia nut, etc.), berries (blueberry, cranberry, blackberry, raspberry, etc.), grape, oyster, olive, loquat, banana, coffee, Date palm, coconut palm, oil palm etc.
  • Trees other than fruit trees tea, mulberry, flowering trees (Satsuki, camellia, hydrangea, sasanqua, shikimi, sakura, yurinoki, crape myrtle, eustoma, etc.), roadside trees (ash, birch, dogwood, eucalyptus, ginkgo, lilac, maple, oak) , Poplar, redwood, fu, sycamore, zelkova, blackfish, Japanese amberjack, moths, pine, pine, spruce, yew, elm, Japanese cypress, etc.), coral jug, dogwood, cedar, cypress, croton, masaki, kanamochi, etc.
  • Lawn Shiba (Nasis, Pleurotus, etc.), Bermudagrass (Neurodonidae, etc.), Bentgrass (Oleoptera, Hykonukagusa, Odonoptera, etc.), Bluegrass (Nagahagusa, Oosuzunokatabira, etc.), Fescue (Oonishi nokegusa, Drosophila, etc.) , Grass, etc.), ryegrass (rat, wheat, etc.), anemonefish, and blue whale.
  • Crop includes genetically modified crops.
  • the harmful arthropod control agent of the present invention may be mixed or used in combination with other insecticides, acaricides, nematicides, fungicides, plant growth regulators, herbicides, synergists and safeners. it can.
  • active ingredients of such insecticides, acaricides, nematicides, fungicides, herbicides, synergists and safeners are shown below.
  • rin cyphenothrin, alpha-cypermethrin, zeta-permethrin, lambda-cyhalothrin, gammacyhalothrin (gammathrin) ), Tau-fluvalinate, metofluthrin, profluthrin, dimethylfluthrin, 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl (EZ)-(1RS) , 3RS; 1RS, 3SR) -2,2-dimethyl-3-prop-1-eni Cyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4-methylbenzyl (EZ)-(1RS, 3RS; 1RS, 3SR) -2,2-dimethyl-3-prop-1-enylcyclopropanecarboxy And 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl (1RS, 3RS; 1RS, 3SR) -2,2-d
  • Neonicotinoid compounds imidacloprid, nitenpyram, acetamiprid, thiamethoxam, thiacloprid, dinotefuran and dinotefuran (dinoteurine).
  • Phenylpyrazole compounds Acetoprole, etiprole, fipronil, vaniliprole, pyriprole, and pyrafluprole.
  • Bt toxin Live spores and produced crystal toxins derived from Bacillus thuringiensis, and mixtures thereof;
  • Hydrazine compounds Chromafenozide, halofenozide, methoxyphenozide, and tebufenozide.
  • Insecticide Active Ingredients Machine oil, nicotine-sulfate; avermectin, bromopropyrate, buprofezin, chlorfenapyr, chlorphenapyr Ritranol, cyromazine, DD (1,3-Dichloropropene), emamectin benzoate, fenazaquin, flupirroprene, flupyrazolen , Indoxacarb, methoxadiazone, milbemycin-A, pymetrozine, pyridalyl, pyriprosul, spiromidol, spinodulsulfide tolfenpyrad, triazamate, flubendiamide, repimectin, arsenous acid, benclothiaz, lime nitrogen calcium lime ulfide, chlordane, DDT, DSP, flufenerim, flonicamid, flurimfen, formatenate, metham-ammonium, metam-ammonium
  • Active ingredients of acaricides acequinocyl, amitraz, benzoximate, bifenaate, phenisobromolate (BS), chinomethionate (BS), chinomethionate (BS) chlorfenson, clofentezine, cyflumetofene, kelsen (dicofol), etoxazole, fenbutatin oxide (fenbutafen), fenothiocarbene roximate, fluacrylpyrim, fluproxyfen, hexythiazox, propargite (BPPS), polynactin complex (pyridene), pyridaben (pyriben) (Tetradifon), spirodiclofen, spiromesifen, spirotetramat, amidoflumet, and cenopyrafen.
  • BS phenisobromolate
  • BS chinomethionate
  • BS chinomethionate
  • Active ingredients of nematicides DCIP, fostiazate, levamisole hydrochloride, methylisothiocyanate, morantel tartrate, and imiciafos.
  • Active ingredients of fungicides Propiconazole, Prothioconazole, Triadimenol, Prochloraz, Penconazole, Tebuconazole, Tebuconazole, Tebuconazole , Bromuconazole, epoxiconazole, difenoconazole, cyproconazole, metconazole, triflumazole, triflumizole Tetraconazole, microbutanil, fenbuconazole, hexaconazole, fluquinconazole, triticonazole, triticonazole, triticonazole, triticonazole Azole fungicidal compounds such as flutriafol; Cyclic amine bactericidal compounds such as fenpropimorph, tridemorph, fenpropidin; Benzimidazole fungicidal compounds such as carbendezim, benomyl, thiabendazole, thiophanate-methyl; Procymid
  • Active ingredients of plant growth regulators Ethephon, chlormequat-chloride, mepiquat-chloride, gibberellin A3 (Gibberellin A3), abscisic acid Kinetin, benzyladenine, 1,3-diphenylurea, forchlorfenuron, thidiazuron, 4-oxo-4- (2-phenylethyl) aminobutyric acid, 5- (trifluoro) Methyl) benzo [b] thiophene-2-carboxylate and 5- (trifluoromethyl) benzo [b] thio Fen-2-carboxylic acid.
  • Triazine herbicidal compounds atrazine, ametrine, cyanazine, simazine, propazine, simetrin, dimethamethrin (dimethymetrine) ), Triaziflam, and indaziflam.
  • Bipyridinium herbicidal compound paraquat and diquat.
  • Hydroxybenzonitrile herbicidal compounds bromoxynil and ioxynil.
  • Dinitroaniline herbicidal compounds pendimethalin, prodiamine, and trifluralin.
  • Organophosphorus herbicidal compounds amiprofos-methyl, butamifos, bensulide, piperophos, anilofos, glyphosate, glufosinate, glufosinate, glufosinate P (glufosinate-P), and bialaphos.
  • Carbamate herbicidal compounds di-allate, tri-allate, EPTC, butyrate, beniocarb, esprocarb, molinate, dimepiperate (Swep), chlorpropham, phenmedifam, phenisopham, piributicarb, and asuram.
  • Acid amide herbicidal compounds propanil, propyzamide, bromobutide, and etobanzanide.
  • Chloroacetanilide herbicidal compounds acetochlor, acechlor, butachlor, dimethenamide, propachlor, metazachlor, metrachlor or totrachlor pretilachlor, tenylchlor, and petoxamide.
  • Diphenyl ether herbicidal compounds aciflufen-sodium, bifenox, oxyfluorfen, lactofen, fomesafen, clomethoxynfen, and clomethoxynylphen.
  • Cyclic imide herbicidal compounds oxadiazon, cinidon-ethyl, carfentrazone-ethyl, sulfentrazone, full-microlac-pentyl, flumi-lacyl-pentyl Oxazine (flumioxazin), pyraflufen-ethyl, oxadiargyl, pentoxazone, fluthiacet-methyl, phenafenezene (butafenzil) zone), and saflufenacil (saflufenacil).
  • Trione oxime herbicidal compounds alloxydim-sodium, cetoxydim, butoxydim, crestodim, cloxydimim, cycloxidim, texydimym (Traxydim), and profoxydim.
  • sulfonylurea herbicidal compounds chlorsulfuron, sulfomethuron-methyl, metsulfuron-methyl, chlorimuron-ethyl, trivenuron methyl (18) tribenuron-methyl, triasulfuron, bensulfuron-methyl, thifensulfuron-methyl, pyrazosulfuron-methyl, urmisyl-uryl Nicosulfuron (nico) ulfuron, amidosulfuron, cinosulfuron, imazosulfuron, rimsulfuron, halosulfuron-thulfuron, sulfuluron-thulfuron , Triflusulfuron-methyl, flazasulfuron, cyclosulfuron, flupirsulfuron, sulfosulfuron, azulsulfuron Azulsulfuron, ethoxysulfuron, oxasulfuron, iod
  • Benzocor active ingredient of safeners, cloquintocet-mexyl, cyometrinil, dichlormid, fenchlorazole-lu, fluchlorizol-ol, fluchlorimol , Furilazole, mefenpyr-diethyl, MG191, oxabetrinil, aldidochlor, isoxadifen-ethyl, cyprodesulfide (cyprodesulfide) fluxofenim), 1,8- naphthalic anhydride (1,8-naphthalic anhydride), and AD-67.
  • the compound of the present invention and compound (2) have geometric isomers derived from the carbon-nitrogen double bond present in the oxime moiety, and in some cases, both isomers can be separated.
  • geometric isomers derived from double bonds existing in the oxime moiety are E isomers.
  • Reference production example 1 100 ml of THF, 22.0 g (220 mmol) of cyclohexanol and 8.80 g (220 mmol) of sodium hydride were added to 31.7 g (200 mmol) of 1,3-dimethyl-5-chloropyrazole-4-carbaldehyde and stirred at room temperature for 2 hours. did. 1M Hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and concentrated.
  • Reference production example 3 200 ml of THF and 34.2 g (287 mmol) of thionyl chloride were added to 40.6 g (192 mmol) of 3,5-difluoro-4-trifluoromethylbenzyl alcohol, and the mixture was stirred at room temperature for 30 minutes. Water was added to the reaction mixture, and the mixture was stirred for 30 minutes, extracted with tertiary butyl methyl ether, and the organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and saturated brine. The obtained organic layer was dried over magnesium sulfate, filtered and concentrated.
  • a part represents a weight part.
  • Formulation Example 1 9 parts of the compound of the present invention is dissolved in 37.5 parts of xylene and 37.5 parts of dimethylformamide. To this, 10 parts of polyoxyethylene styrylphenyl ether and 6 parts of calcium dodecylbenzenesulfonate are added and stirred and mixed. Obtain an emulsion.
  • Formulation Example 2 5 parts of Solpol 5060 (registered trademark of Toho Chemical) is added to 40 parts of the compound of the present invention and mixed well. 32 parts of Carplex # 80 (registered trademark of Shionogi & Co., synthetic silicon hydroxide fine powder), 300 mesh diatomaceous earth Add 23 parts and mix with juice mixer to obtain wettable powder.
  • Solpol 5060 registered trademark of Toho Chemical
  • Carplex # 80 registered trademark of Shionogi & Co., synthetic silicon hydroxide fine powder
  • 300 mesh diatomaceous earth Add 23 parts and mix with juice mixer to obtain wettable powder.
  • Formulation Example 3 Add 3 parts of the compound of the present invention, 5 parts of synthetic hydrous silicon oxide fine powder, 5 parts of sodium dodecylbenzenesulfonate, 30 parts of bentonite and 57 parts of clay, and stir and mix well, and then add an appropriate amount of water to these mixtures. Further, the mixture is stirred, granulated by a granulator, and dried by ventilation to obtain a granule.
  • Formulation Example 4 4.5 parts of the compound of the present invention, 1 part of synthetic hydrous silicon oxide fine powder, 1 part of Doreles B (manufactured by Sankyo Co., Ltd.) as a flocculant and 7 parts of clay are mixed well in a mortar, and then stirred and mixed in a juice mixer. 86.5 parts of cut clay is added to the resulting mixture and mixed well with stirring to obtain a powder.
  • Formulation Example 5 By mixing 10 parts of the present compound (1), 35 parts of a mixture of polyoxyethylene alkyl ether sulfate ammonium salt and white carbon (weight ratio 1: 1) and 55 parts of water, and finely pulverizing by a wet pulverization method, A formulation is obtained.
  • Formulation Example 7 0.1 part of the compound of the present invention and 49.9 parts of Neothiozole (Chuo Kasei Co., Ltd.) are placed in an aerosol can, and after mounting an aerosol valve, 25 parts of dimethyl ether and 25 parts of LPG are filled into the aerosol can. An oily aerosol is obtained by adding shaking to the aerosol can and mounting an actuator.
  • Neothiozole Cho Kasei Co., Ltd.
  • Formulation Example 8 0.6 parts of the compound of the present invention, 0.01 part of BHT, 5 parts of xylene, 3.39 parts of deodorized kerosene and 1 part of an emulsifier ⁇ Atmos 300 (registered trademark of Atmos Chemical) ⁇ and 50 parts of distilled water
  • a valve portion is attached, and 40 parts of a propellant (LPG) is pressure-filled through the valve to obtain an aqueous aerosol for each of the above compounds.
  • LPG propellant
  • Test example 2 The preparation of the compound of the present invention obtained in Formulation Example 5 was diluted with water so that the active ingredient concentration was 500 ppm to prepare a test drug solution.
  • Test example 3 The preparation of the compound of the present invention obtained in Formulation Example 5 was diluted with water so that the active ingredient concentration was 500 ppm to prepare a test drug solution. 10 ml of the test chemical solution was sprayed on rice seedlings in the second leaf development stage planted in a polyethylene cup. After air drying, 20 3-4 instar larvae of the green planthopper (Nilaparvata lugens) were released and stored in a greenhouse at 25 ° C. Six days later, the number of brown planthoppers infested with rice was investigated, and the control value was determined by the following formula.
  • Control value (%) ⁇ 1 ⁇ (Cb ⁇ Tai) / (Cai ⁇ Tb) ⁇ ⁇ 100
  • the character in a formula represents the following meaning.
  • Tai number of insects during observation of the treated group
  • the control value was 90% or more.
  • Test example 4 The preparation of the compound of the present invention obtained in Formulation Example 5 was diluted with water so that the active ingredient concentration was 500 ppm to prepare a test drug solution. Meanwhile, about 30 cotton aphids (Aphis gossypii) were inoculated into cucumber seedlings (first true leaf development stage) planted in plastic cups and left for 1 day. Each of these seedlings was sprayed with 20 ml of the test chemical solution. Six days after spraying, the number of live cotton aphids that parasitized on the leaves of the cucumber was examined, and the control value was determined by the following formula.
  • Control value (%) ⁇ 1 ⁇ (Cb ⁇ Tai) / (Cai ⁇ Tb) ⁇ ⁇ 100
  • the character in a formula represents the following meaning.
  • Tai number of insects during observation of the treated group
  • the control value was 90% or more.
  • Test Example 5 The preparation of the compound of the present invention obtained in Formulation Example 5 was diluted with water so that the active ingredient concentration was 500 ppm to prepare a test drug solution.
  • the root of a cucumber seedling (first true leaf development stage) in which the soil was washed off was immersed in 5 ml of the test chemical solution, and 30 cotton aphids (all stages) were inoculated on the cucumber leaf surface one day after the treatment. Further, after 7 days, the number of viable cotton aphids parasitic on the cucumber leaves was investigated, and the control value was determined by the following formula. Control value (%) ⁇ 1 ⁇ (Cb ⁇ Tai) / (Cai ⁇ Tb) ⁇ ⁇ 100
  • the character in a formula represents the following meaning.
  • Test Example 6 The preparation of the compound of the present invention obtained in Formulation Example 5 was diluted with water so that the active ingredient concentration was 500 ppm to prepare a test drug solution. Forty-nine spider mites (Tetranychus urticae) female adults were released to the kidney beans immediately after the development of primary leaves. On the next day, the test chemical solution was sprayed in an amount of the chemical solution dripping with a spray gun. It placed in a constant temperature breeding room (25 degreeC), the number of living insects was investigated 7 days after the process, and the control value was calculated
  • required by the following formula. Control value (1 ⁇ number of live female adults in treated group / number of live female adults in untreated group) ⁇ 100 As a result, in the treatment of the compound of the present invention, a control value of 90% or more was shown.
  • Test Example 7 The preparation of the compound of the present invention obtained in Formulation Example 5 was diluted with water so that the active ingredient concentration was 500 ppm to prepare a test drug solution. Forty-nine spider mites (Tetranychus urticae) female adults were released to the kidney beans immediately after the development of primary leaves. On the next day, the test chemical solution was sprayed in an amount of the chemical solution dripping with a spray gun. It placed in a constant temperature breeding room (25 degreeC), the number of living insects was investigated 13 days after the process, and the control value was calculated
  • required by the following formula. Control value (1 ⁇ number of live female adults in treated group / number of live female adults in untreated group) ⁇ 100 As a result, in the treatment of the compound of the present invention, a control value of 90% or more was shown.
  • Test Example 8 The preparation of the compound of the present invention obtained in Formulation Example 5 was diluted with water so that the active ingredient concentration was 500 ppm to prepare a test drug solution.
  • a filter paper of the same size was laid on the bottom of a polyethylene cup having a diameter of 5.5 cm, 0.7 ml of the test chemical solution was dropped onto the filter paper, and 30 mg of sucrose was uniformly added as a bait.
  • the compound of the present invention has a controlling activity against harmful arthropods, it is useful as an active ingredient of a harmful arthropod controlling agent.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
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  • Engineering & Computer Science (AREA)
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Abstract

La présente invention se rapporte à un composé pyrazole représenté par la formule (1), qui est efficace en tant qu'agent de lutte contre les arthropodes nuisibles.
PCT/JP2015/063726 2014-05-22 2015-05-13 Composé pyrazole WO2015178262A1 (fr)

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JP2014105881 2014-05-22

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH03227975A (ja) * 1990-02-02 1991-10-08 Sumitomo Chem Co Ltd ピラゾール誘導体およびそれを有効成分とする殺虫、殺ダニ剤
JP2003026647A (ja) * 2001-05-09 2003-01-29 Sumitomo Chem Co Ltd マロノニトリル化合物及びその用途
JP2011500574A (ja) * 2007-10-09 2011-01-06 ダウ アグロサイエンシィズ エルエルシー 殺虫性置換アジニル誘導体
JP2015086178A (ja) * 2013-10-31 2015-05-07 住友化学株式会社 ピラゾール化合物及びその有害生物防除用途
JP2015086177A (ja) * 2013-10-31 2015-05-07 住友化学株式会社 ピラゾール化合物及びその有害生物防除用途

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH03227975A (ja) * 1990-02-02 1991-10-08 Sumitomo Chem Co Ltd ピラゾール誘導体およびそれを有効成分とする殺虫、殺ダニ剤
JP2003026647A (ja) * 2001-05-09 2003-01-29 Sumitomo Chem Co Ltd マロノニトリル化合物及びその用途
JP2011500574A (ja) * 2007-10-09 2011-01-06 ダウ アグロサイエンシィズ エルエルシー 殺虫性置換アジニル誘導体
JP2015086178A (ja) * 2013-10-31 2015-05-07 住友化学株式会社 ピラゾール化合物及びその有害生物防除用途
JP2015086177A (ja) * 2013-10-31 2015-05-07 住友化学株式会社 ピラゾール化合物及びその有害生物防除用途

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