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WO2015064725A1 - Composé de pyrazole et son application pour la lutte contre les nuisibles - Google Patents

Composé de pyrazole et son application pour la lutte contre les nuisibles Download PDF

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Publication number
WO2015064725A1
WO2015064725A1 PCT/JP2014/079004 JP2014079004W WO2015064725A1 WO 2015064725 A1 WO2015064725 A1 WO 2015064725A1 JP 2014079004 W JP2014079004 W JP 2014079004W WO 2015064725 A1 WO2015064725 A1 WO 2015064725A1
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WIPO (PCT)
Prior art keywords
compound
present
reaction
compounds
methyl
Prior art date
Application number
PCT/JP2014/079004
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English (en)
Japanese (ja)
Inventor
英樹 采女
康 片桐
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住友化学株式会社
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Publication of WO2015064725A1 publication Critical patent/WO2015064725A1/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
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • A61K31/4155—1,2-Diazoles non condensed and containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates to a pyrazole compound and its use for controlling pests.
  • An object of the present invention is to provide a novel compound having an excellent control activity against pests.
  • the present inventor has found that the pyrazole compound represented by the following formula (1) has an excellent controlling effect on pests. It came to. That is, the present invention is as follows. [1] Formula (1) [Wherein, R represents a cyclohexyl group, a 3-cyclohexen-1-yl group or a 4-methylcyclohexyl group. ] A pyrazole compound represented by the following (hereinafter referred to as the present compound). [2] A pest control agent comprising a pyrazole compound represented by the formula (1) and an inert carrier. [3] A method for controlling pests, which comprises applying an effective amount of the pyrazole compound represented by the formula (1) to pests or habitats of pests. [The invention's effect]
  • the compound of the present invention is useful as an active ingredient of a pest control agent because it has an excellent control activity against pests.
  • 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.
  • a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, a methanesulfonyloxy group, or trifluoromethane.
  • alkylsulfonyloxy groups such as a sulfonyloxy group
  • arylsulfonyloxy groups such as a benzenesulfonyloxy group and a p-toluenesulfonyloxy group.
  • the pyrazole compound represented by the formula (1) can be mixed with, for example, hydrochloric acid, sulfuric acid or phosphoric acid to take an agriculturally acceptable salt form.
  • the compounds of the present invention also include pyrazole compounds in the form of such agriculturally acceptable salts.
  • 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.
  • the compound of the present invention may have isomers derived from asymmetric carbon atoms, and the present invention includes each of them and a mixture thereof.
  • the compound of the present invention may have isomers derived from the relative configuration between substituents, and the present invention includes each of them and a mixture 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).
  • R represents the same meaning as described above, and 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, Ethers such as ethylene 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, heptane, etc .;
  • the amount of compound (3) used in the reaction is usually 0.5 to 5 moles relative to 1 mole 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 -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 used in the reaction is usually 1 to 5 mol with respect to 1 mol of compound (2).
  • the reaction can also be performed in the presence of a phase transfer catalyst.
  • phase transfer catalyst used in the reaction include quaternary ammonium salts such as tetrabutylammonium bromide and benzyltriethylammonium chloride.
  • the amount of the phase transfer catalyst used in the reaction is usually 0.01 to 0.5 mol with respect to 1 mol of the compound (2).
  • the reaction temperature of the reaction is usually in the range of 0 to 100 ° C.
  • 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 also be purified by chromatography, recrystallization and the like.
  • the compound of the present invention can also be produced by reacting compound (4) with compound (5).
  • R represents the same meaning as described above.
  • 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.
  • Nitriles 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; And halogenated hydrocarbons such as dichloroethane, 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 used here include hydrochloric acid, sulfuric acid, and phosphoric acid.
  • the amount of the compound (5) used in the reaction is usually 1 to 5 mol with respect to 1 mol of the compound (4).
  • the reaction can also be performed in the presence of an acid.
  • the acid used in the reaction include acetic acid, hydrochloric acid, sulfuric acid, and phosphoric acid.
  • the amount of the acid used in the reaction is usually 0.01 to 10 mol per 1 mol of compound (4).
  • the reaction can also be performed in the presence of a base.
  • Examples of the base used in the reaction include triethylamine, pyridine, sodium hydrogen carbonate, sodium carbonate, potassium carbonate, sodium hydroxide, and potassium hydroxide.
  • the amount of the base used in the reaction is usually 0.01 to 10 mol with respect to 1 mol of compound (4).
  • the reaction can also be carried out in the presence of molecular sieve, anhydrous magnesium sulfate, anhydrous sodium sulfate and the like.
  • the amount of these compounds is usually 1 to 10 grams per 1 gram of compound (4).
  • the reaction temperature of the reaction 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 also be purified by chromatography, recrystallization and the like.
  • the compound of the present invention can also be produced by reacting compound (6) with compound (7).
  • R represents the same meaning as defined above, 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 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 Sulfoxides; sulfolanes; halogenated hydrocarbons such as 1,2-dichloroethane, chloroform, chlorobenzene; and mixtures thereof.
  • the amount of compound (7) used in the reaction is usually 0.5 to 5 moles relative to 1 mole 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 -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 used in the reaction is usually 1 to 5 mol with respect to 1 mol of compound (6).
  • the reaction can also be performed in the presence of a phase transfer catalyst.
  • phase transfer catalyst used in the reaction examples include quaternary ammonium salts such as tetrabutylammonium bromide and benzyltriethylammonium chloride.
  • the amount of the phase transfer catalyst used in the reaction is usually 0.01 to 0.5 mol with respect to 1 mol of the compound (6).
  • the reaction temperature of the reaction is usually in the range of 0 to 100 ° C.
  • 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 also be purified by chromatography, recrystallization and the like.
  • Compound (5) can be produced by reacting compound (10) with hydrazine monohydrate.
  • the reaction is usually performed in a solvent.
  • the solvent used in the reaction include alcohols such as methanol, ethanol and isopropyl alcohol.
  • the amount of hydrazine monohydrate used in the reaction is usually 1 to 5 mol with respect to 1 mol of compound (10).
  • the reaction temperature of the reaction is usually in the range of 50 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 also be purified by chromatography, recrystallization and the like.
  • Compound (10) can be produced by reacting compound (11) with compound (12) 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, heptane, and the like.
  • Aliphatic hydrocarbons such as 1,2-dichloroethane, chloroform, chlorobenzene; and mixtures thereof.
  • the amount of the compound (12) used in the reaction is usually 0.5 to 2 mol with respect to 1 mol of the compound (11).
  • the amount of triphenylphosphine used in the reaction is usually 0.5 to 2 mol with respect to 1 mol of compound (11).
  • the amount of diethyl azodicarboxylate used in the reaction is usually 0.5 to 2 moles relative to 1 mole of compound (11).
  • the reaction temperature of the reaction is usually in the range of 0 to 50 ° 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 also be purified by chromatography, recrystallization and the like.
  • compound (3), compound (7), compound (8), compound (9), compound (11) and compound (12) are known or known from known compounds. It can be manufactured according to the method.
  • pests for which the compounds of the present invention are effective include harmful arthropods and nematodes such as harmful insects and harmful mites. Specific examples of such pests include the following.
  • 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 (Brevicoryne brassicae), snowy aphids (Aphis spiraecola), tulip beetle aphids (Aphis spiraecola) Acrosiphum euphorbiae, potato beetle aphids (Aulacorthum solani), wheat leaf aphids (R
  • Stink bugs such as stink bugs (Riptortus clavetus), spider helicopter bugs (Leptocorisa chinensis), bark beetle (Eysarcoris parvus), winged beetle (Halyomorpha mista) whitefly species such as svaporiarum, tobacco whitefly (Bemisia tabaci), citrus whitefly (Dialeurodes citri), Alecananthus spiniferus (Aleurocanthus spiraferus) citri), Ruby Roe beetle (Ceroplastes rubens), Iceria scale insect (Icerya purchasi), Fujino scale insect (Pranococcus kraunhiae), Swan scale scale (Pseudococcus longis) nis), scale insects such as Pseudauracapaspis pentagona, bed bugs, bed bugs such as Cimectularus, and whales.
  • stink bugs Rhiptort
  • 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 (Lissohoprus oryzophilus), Azuki beetle (Callosobrchuchus Kunststoffsis), Echonocnemus quail (Echinocnemus squatium) onomus grandis), weevils such as grass reed weevil (Sphenophorus venatus), Chai Loco Meno mealworm (Tenebrio molitor), mealworm such as red flour beetle (Tribolium castaneum), Inedorooimushi (Oulema or
  • Pterodoptera Tocusama grasshopper (Locusta migratoria), Kera (Gryllotalpa africana), Oxya yezoensis, Lobster (Oxya japonica) and crickets.
  • Lepidoptera Cat fleas (Ctenocephalides felis), dog fleas (Ctenocephalides canis), human fleas (Pulex irritans), keops mud mines (Xenopsylla cheopeis) 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.
  • White-eye pests sheep lice (Dalmalinia ovis), bovine lice (Dalmalinia bovis), chicken lice (Menopon gallinae), dog lice (Trichodictes canis), cat wings, 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).
  • Nematodes rice Shin Galle nematode (Aphelenchoides besseyi), strawberry menu nematode (Nothotylenchus acris), sweet potato root-knot nematode (Meloidogyne incognita), northern root-knot nematode (Meloidogyne hapla), Java root-knot nematode (Meloidogyne javanica), soybean cyst nematode (Heterodera glycines), Potato cyst nematode (Globodera rostochiensis), southern nematode crested pea (Pratylenchus coffeae), barley nematode nematode (Pratylenchus neglectus).
  • 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, Gyptotermes nakajimai, Caterpillars (Glyptotermes fuscus), Gyptotermes kodamai Moto termites (Glyptotermes kushimensis), giant termite (Hodotermopsis japonica), Kou Shu Ye termite (Coptotermes guangzhoensis), Amami termites (Reticulitermes miyatakei), R.
  • Mite order pests Taninychus urticae, Kantawa spider mite (Tetranychus kanzawai), citrus spider mite (Panonychus citri), mite spider mite (Pananycos ulmi), spider mite pistula mite (Panthonychus urmi), spider mite pistula mite (Panthonychus urmi), spider mite pistula mite (Panthonychus urmi); Tomato rust mites (Aculops lycopersici), Chinese radish mites (Calacarus carinatus), Chinese mosquito mites (Acaphylla theavagrans), Green rust mites (Eriophys chibaensis), Apple rust mites Fushidani such, dust mite such as Chanohokoridani (Polyphagotarsonemus latus), southern Hime Himehadani such as spider mites (Brevipalpus phoenici
  • pteronyssinus (Dermatophagoides ptrenyssnus) Lion ticks, such as Cheyletus eruditus, Scarlet ticks (Cheyletus malacensis), Scarlet ticks (Cheyletus mooreii), Tiger ticks (Cheyletie) tick mites such as ll. Ornithonysus sylvairum, duck spider (Dermanysussus gallinae), etc .; Lip and limb class: Geeu (Thereunema hilgendorfi), Tobizukade (Scorpendra subspinipes) and the like. Double leg class: Oxidus gracilis, Nedyopus tambanus, etc. Isopods: Armadillium vulgare, etc. Gastropoda: Limax marginatus, Limax flavus, etc.
  • the pest control agent of the present invention contains the compound of the present invention and an inert carrier.
  • the pesticidal 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, liquid carrier, gaseous carrier, etc., and if necessary, a surfactant or other formulation adjuvant is added Emulsions, oils, powders, granules, wettable powders, flowables, microcapsules, aerosols, smokers, poisonous baits, resin formulations, shampoos, pastes, foams, carbon dioxide formulations, It is formulated into tablets.
  • the pest 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).
  • Polyester resins such as 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 pest control method of the present invention is carried out by applying an effective amount of the compound of the present invention to pests directly and / or to pest habitats (plants, soil, households, animal bodies, etc.).
  • the pest control method of the present invention is usually used in the form of the pest control agent of the present invention.
  • the application amount is usually 1 to 10,000 g in terms of the amount of the compound of the present invention per 10,000 m 2 .
  • the pest 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 0.01 to 10000 ppm. Agents, powders, etc. are usually applied as they are.
  • preparations and water dilutions of the preparations may be sprayed directly on pests or plants such as crops to be protected from pests, and in order to control pests that inhabit cultivated soil. You may process to soil.
  • 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 the amount of the compound of the present invention per 1 m 2 treated area when treated on the surface, usually 0.01.
  • 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 pest 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 aerosols, smoke, poisonous bait, etc. as they are.
  • the pest control agent of the present invention When the pest control agent of the present invention is used for controlling ectoparasites of cattle, horses, pigs, sheep, goats, chickens, small animals such as dogs, cats, rats, mice, etc., a method known in veterinary medicine Can be used on animals.
  • a method known in veterinary medicine Can be used on animals.
  • systemic suppression for the purpose of 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 pest control agent of the present invention can be used in farmland where the following “crop” is 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 pest control agent of the present invention can be used in combination or in combination with other insecticides, acaricides, nematicides, fungicides, plant growth regulators, herbicides, synergists and safeners.
  • active ingredients of such insecticides, acaricides, nematicides, fungicides, herbicides, synergists and safeners are shown below.
  • thrin phenothrin, cyphenothrin, alpha-cypermethrin, zeta-cypermethrin, lambda cihalothrin (lambda-cythhalothrin) ), Furamethrin, tau-fluvalinate, methfluthrin, profluthrin, dimethylfluthrin, 2,3,5,6-tetrafluoro-4- (methoxymethyl) benzyl EZ)-(1RS, 3RS; 1RS, 3S ) -2,2-dimethyl-3-prop-1-enylcyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4-methylbenzyl (EZ)-(1RS, 3RS; 1RS, 3SR) -2 , 2-dimethyl-3-prop-1-enylcyclopropanecarboxylate, and 2,3,5,6-tetrafluoro-4- (methoxymethyl) benz
  • 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.
  • Machine oil (nicotine-sulfate); avermectin (avermectin-B), bromopropyrate, buprofezin, chlorphenapyr Ritranol, cyromazine, DD (1,3-Dichloropropene), emamectin benzoate, fenazaquin, flupirahydroprene , Indoxacarb, methoxadiazone, milbemycin-A, pymetrozine, pyridalyl, pyriprosul, spiromidol, spinomidol tolfenpyrad, triazamate, flubendiamide, repimectin, arsenous acid, benclothiaz, lime nitrogen calcium lime ulfide, chlordane, DDT, DSP, flufenerium, flonicamid, flurimfen, formatenate, metam-ammonium, metam-ammonium sodium, methyl
  • 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; Benzimidazolic fungicidal compounds such as carbendezim, benomyl, thiabendazole, thiophanate-methyl; Procymid
  • Active ingredient of herbicide (1) phenoxy fatty acid herbicidal compound 2,4-PA, MCP, MCPB, phenothiol, mecoprop, fluroxypyr, triclopyr, clomeprop Naproanilide. (2) Benzoic acid herbicidal compound 2,3,6-TBA, dicamba, clopyralid, picloram, aminopyralid, quinclorac, and quinmerac. (3) Urea herbicidal compounds diuron, linuron, chlortoluron, isoproturon, fluometuron, isouron, tebuthiuron, tebuthiuron, tebuthiuron , Cumyluron, daimuron, and methyl-daimuron.
  • 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.
  • Organic phosphorus herbicidal compounds amiprofos-methyl, butamifos, bensulide, piperophos, anilofos, glyphosate, glufosinate, glufosinate, glufosinate P (glufosinate-P), and bialaphos.
  • 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, and clomethoxynfen.
  • Triketone herbicidal compounds isoxaflutole, benzobicyclon, sulcotrione, mesotrione, tembotrione, and tefriltrione.
  • Aryloxyphenoxypropionic acid herbicidal compound clodinafop-propargyl, cyhalofop-butyl, diclohop-methyl, phenoxaprop-ethyl, fenoxaprop-propyl Fluazifop-butyl, haloxyhop-methyl, and quizalofop-ethyl, metamihop.
  • Trionoxime herbicidal compounds alloxydim-sodium, cetoxydim, butoxydim, crestodim, cloxydimim, cycloxidim, texydimym (Traxydim), and profoxydim.
  • MLK 264 N- (2-ethylhexyl) -8,9,10-trinorborn-5-ene-2,3-dicarboximide
  • N-decylimidazole WARF-antiresistant, TBPT, TPP, IBP, PSCP, methyl iodide (CH 3 I), t-phenylbutenone ( t-phenylbut
  • Active ingredients of safeners Benoxacol, cloquintocet-mexyl, thiomethrinil, dichlormid, fenchlorazole-l, fluchlorizol , Furilazole, mefenpyr-diethyl, MG191, oxabetrinil, alidochlor, isoxadifen-ethyl, cyprodesulfide fluxofenim), 1,8- naphthalic anhydride (1,8-naphthalic anhydride), and AD-67.
  • the compounds (1-1) to (1-3) and the compounds (2-1) to (2-3) of the present invention have geometric isomers derived from a carbon-nitrogen double bond existing in the oxime moiety. In some cases, both isomers can also be separated. In the following examples, unless otherwise specified, geometric isomers derived from double bonds existing in the oxime moiety are E isomers.
  • Reference production example 2 1.93 g (37.4 mmol) of 1,3-dimethyl-5-chloropyrazole-4-carbaldehyde, 50 ml of THF, 4.70 g (41.2 mmol) of trans-4-methylcyclohexanol, and 1.65 g of sodium hydride (41.2 mmol) was added and stirred at 40 degrees for 5 hours. 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.
  • the resulting crude 1,3-dimethyl-5- (3-cyclohexen-1-yloxy) pyrazole-4-carbaldehyde was mixed with 20 ml of ethanol, 4.17 g (60.0 mmol) of hydroxylamine hydrochloride, and sodium acetate 8 .23 g (100 mmol) was added, and the mixture was stirred for 30 minutes with heating under reflux. To the reaction mixture was added saturated brine, and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated.
  • a part represents a weight part.
  • Formulation Example 1 9 parts of any one of the compounds (1-1) to (1-3) of the present invention are dissolved in 37.5 parts of xylene and 37.5 parts of dimethylformamide, and 10 parts of polyoxyethylene styrylphenyl ether and dodecyl are dissolved in this. Add 6 parts of calcium benzenesulfonate and mix well with stirring to obtain an emulsion.
  • Formulation Example 2 This invention compound (1-1)-(1-3) 40 parts of Solpol 5060 (trade name of Toho Chemicals) is added to 40 parts and mixed well, and Carplex # 80 (Shionogi Pharmaceutical registered trademark). Name, synthetic hydrous silicon oxide fine powder) 32 parts, 300 mesh diatomaceous earth 23 parts are added and mixed with a juice mixer to obtain a wettable powder.
  • Formulation Example 3 3 parts of any one of the compounds (1-1) to (1-3) of the present invention, 5 parts of a synthetic hydrous silicon oxide fine powder, 5 parts of sodium dodecylbenzenesulfonate, 30 parts of bentonite and 57 parts of clay are added and stirred well. Next, an appropriate amount of water is added to the mixture, and the mixture is further stirred, granulated with a granulator, and dried by ventilation to obtain granules.
  • Formulation Example 4 4.5 parts of any one of the compounds (1-1) to (1-3) of the present invention, 1 part of a synthetic hydrous silicon oxide fine powder, 1 part of Doreles B (manufactured by Sankyo) as a flocculant, and 7 parts of clay Mix well and mix with 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 10 parts of any one of the compounds of the present invention (1-1) to (1-3), 35 parts of a mixture of polyoxyethylene alkyl ether sulfate ammonium salt and white carbon (1: 1 by weight) and 55 parts of water are mixed. And a formulation is obtained by carrying out the fine grinding
  • Formulation Example 7 0.1 part of any one of the compounds (1-1) to (1-3) of the present invention, 49.9 parts of Neothiozole (Chuo Kasei Co., Ltd.) are put into an aerosol can, and 25 parts of An oily aerosol is obtained by filling dimethyl ether and 25 parts of LPG in the aerosol can, shaking the aerosol can, and mounting the actuator.
  • Neothiozole Cho Kasei Co., Ltd.
  • Formulation Example 8 Any one of the compounds (1-1) to (1-3) of the present invention 0.6 part, 0.01 part BHT, 5 parts xylene, 3.39 parts deodorized kerosene and an emulsifier ⁇ Atmos 300 (registered trademark of Atmos Chemical Co., Ltd.) ) ⁇ 1 part mixed and dissolved and 50 parts of distilled water are filled into an aerosol container, a valve part is attached, and 40 parts of propellant (LPG) is pressure-filled through the valve. Get an aerosol.
  • LPG propellant
  • test examples show that the compound of the present invention is effective as an active ingredient of a pest control composition.
  • Test example 2 Each formulation of the present compounds (1-1) to (1-3) 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 Each formulation of the present compounds (1-1) and (1-3) obtained in Formulation Example 5 was diluted with water so that the active ingredient concentration was 500 ppm to prepare a test drug solution.
  • Artificial feed Silk Mate 2S (Nippon Agricultural Industry) placed on the bottom of a 5.5 cm diameter polyethylene cup with the same size filter paper and sliced to a thickness of 2 mm, and any one of the above test chemicals ( 1 mL (500 ppm) was irrigated. After air-drying the test chemical solution, a filter paper having a diameter of 5.5 cm was placed on the artificial feed, and 30 first-instar larvae of Adox ophyces orana were released on the artificial feed, and the lid was capped.
  • Death rate (%) (Number of dead insects / number of test insects) ⁇ 100 As a result, in the treatment with the compounds (1-1) and (1-3) of the present invention, the death rate was 90% or more.
  • Test example 4 Each formulation of the present compounds (1-1) and (1-3) 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 any one of the above test chemicals 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 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 compound of the present invention (1 In the treatment of -1) and (1-3)
  • the control value was 90% or more.
  • Test Example 5 Each formulation of the present compounds (1-1) to (1-3) 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. 20 ml of any one of the above test chemicals was sprayed on the seedlings. 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 compound of the present invention (1 In the treatments of -1) to (1-3), the control value was 90% or more.
  • Test Example 6 Each formulation of the present compounds (1-1) and (1-3) obtained in Formulation Example 5 was diluted with water so that the active ingredient concentration was 500 ppm to prepare a test drug solution. Ten adult adults of Tetanychus urticae were released on the green beans immediately after the development of the primary leaves. On the next day, any one of the above test chemicals was sprayed with a spray gun in such an amount that the chemical was dripping. 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 living female adults in treated group / number of living female adults in untreated group) ⁇ 100 As a result, in the treatment of the present compounds (1-1) and (1-3), the control value was 90% or more.
  • Test Example 7 The preparation of the compound of the present invention (1-1) obtained in Formulation Example 5 was diluted with water so that the active ingredient concentration was 500 ppm to prepare a test drug solution. Ten adult adults of Tetanychus urticae were released on the green beans immediately after the development of the 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 living female adults in treated group / number of living female adults in untreated group) ⁇ 100 As a result, the treatment value of 90% or more was shown in the treatment of the compound (1-1) of the present invention.
  • Test Example 8 Each formulation of the present compounds (1-1) to (1-3) 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 any one of the above test chemicals was dropped on the filter paper, and 30 mg of sucrose was uniformly added as food.
  • the compound of the present invention is useful as an active ingredient of a pest control agent because it has an excellent control activity against pests.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
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  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
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  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
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Abstract

L'invention concerne un composé de pyrazole représenté par la formule (1) (1) [Dans la formule, R représente un groupe cyclohexyle, un groupe 3-cyclohexène-1-yle ou un groupe 4-méthylcyclohexyle] qui a une excellente activité de lutte contre les nuisibles. L'invention concerne également un pesticide qui comprend le composé de pyrazole et un support inerte. L'invention concerne en outre un procédé de lutte contre les nuisibles qui comprend l'application d'une quantité efficace du composé de pyrazole aux nuisibles ou à leurs habitats.
PCT/JP2014/079004 2013-10-31 2014-10-24 Composé de pyrazole et son application pour la lutte contre les nuisibles WO2015064725A1 (fr)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6413086A (en) * 1987-07-07 1989-01-17 Nihon Nohyaku Co Ltd Pyrazole oxime derivative and germicide insecticide and acaricide containing said compound
JPH01197471A (ja) * 1988-02-02 1989-08-09 Nissan Chem Ind Ltd ピラゾールオキシム誘導体および殺虫、殺ダニ、殺菌剤
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
CN1844103A (zh) * 2006-03-22 2006-10-11 南开大学 吡唑肟醚类衍生物和制备及其应用
WO2012083550A1 (fr) * 2010-12-24 2012-06-28 南开大学 Dérivés d'éthers d'oxime pyridylique, leurs procédés de préparation et leurs utilisations

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6413086A (en) * 1987-07-07 1989-01-17 Nihon Nohyaku Co Ltd Pyrazole oxime derivative and germicide insecticide and acaricide containing said compound
JPH01197471A (ja) * 1988-02-02 1989-08-09 Nissan Chem Ind Ltd ピラゾールオキシム誘導体および殺虫、殺ダニ、殺菌剤
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
CN1844103A (zh) * 2006-03-22 2006-10-11 南开大学 吡唑肟醚类衍生物和制备及其应用
WO2012083550A1 (fr) * 2010-12-24 2012-06-28 南开大学 Dérivés d'éthers d'oxime pyridylique, leurs procédés de préparation et leurs utilisations

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