WO2017057121A1 - Composé pyrimidine et son utilisation pour la lutte contre les organismes nuisibles - Google Patents

Composé pyrimidine et son utilisation pour la lutte contre les organismes nuisibles Download PDF

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Publication number
WO2017057121A1
WO2017057121A1 PCT/JP2016/077784 JP2016077784W WO2017057121A1 WO 2017057121 A1 WO2017057121 A1 WO 2017057121A1 JP 2016077784 W JP2016077784 W JP 2016077784W WO 2017057121 A1 WO2017057121 A1 WO 2017057121A1
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Prior art keywords
present
compound
pest control
parts
pests
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PCT/JP2016/077784
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English (en)
Japanese (ja)
Inventor
英樹 采女
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住友化学株式会社
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Publication of WO2017057121A1 publication Critical patent/WO2017057121A1/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
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/42—One nitrogen atom

Definitions

  • the present invention relates to a pyrimidine compound and its use for pest control.
  • Certain pyrimidine compounds are known as active ingredients of pest control agents (see, for example, Patent Documents 1 to 3).
  • An object of the present invention is to provide a novel compound having a controlling activity against pests.
  • a pyrimidine compound represented by the following formula (1) has a control effect on pests, leading to the present invention. It was. That is, the present invention is as follows.
  • Formula (1) A pyrimidine compound represented by the following (hereinafter referred to as the present compound).
  • a pest control agent comprising the compound of the present invention and an inert carrier.
  • a method for controlling pests which comprises applying an effective amount of the compound of the present invention to a pest or a place where the pests grow.
  • the compound of the present invention has a pest control activity against pests, it is useful as an active ingredient of pest control agents.
  • the compound of the present invention may 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 pyrimidine compounds in the form of such agriculturally acceptable salts.
  • 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, Ayuyoto (Pseudaletia sepata), Atoga Estra brassicae, Agrotis ipsilon, Tamanaginawaba (Prusia nigrisigna), Trichopulsia, Heliotis, Helicoberpa, etc.
  • Thrips of the order Thrips thrips (Frankliniella occidentalis), Thrips peri, etc.
  • 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, house flies (Musca domestica), house flies such as Muscina stabulans, fly flies, moth flies, moth flies, i elia 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), Red-bellied lion (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 insects German cockroaches (Blatella germanica), Black cockroaches (Periplaneta fuliginosa), Cockroach cockroach (Periplaneta americana), Japanese cockroach (Peripraneta brunat)
  • 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 inert carrier represents a bulking agent, a diluent or the like used in the field of prevention and agriculture.
  • the pest 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 a surfactant or other formulation adjuvant is added as necessary.
  • 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). , Activated carbon, calcium carbonate, hydrated silica, etc.), fine fertilizers such as chemical fertilizers (ammonium sulfate, phosphorous acid, ammonium nitrate, urea, ammonium chloride, etc.) and granular materials.
  • liquid carrier examples include water, alcohols (methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, 2-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, myristic acid) Isopropyl, ethyl oleate, diisopropyl adipate, diisobutyl adipate, propylene glycol monomethyl ether acetate, etc.
  • 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-t-butyl-4-methylphenol), BHA (2-t- And a mixture of butyl-4-methoxyphenol and 3-t-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 (isopropy
  • bait base examples include cereal flour, vegetable oil, sugar, crystalline cellulose, and the like, and if necessary, antioxidants such as BHT and nordihydroguaiaretic acid, preservatives such as dehydroacetic acid, and pepper.
  • antioxidants such as BHT and nordihydroguaiaretic acid
  • preservatives such as dehydroacetic acid, and pepper.
  • Additives such as anti-fouling agents by children and pets such as powder, cheese flavor, onion flavor, peanut oil and other pest-attracting flavors.
  • Pests can be controlled by applying the pest control agent of the present invention to pests and / or habitats of pests.
  • the pest control method of the present invention is carried out by applying an effective amount of the compound of the present invention to a pest and / or a pest habitat (plant, soil, household, animal body, etc.).
  • a pest and / or a pest habitat plant, soil, household, animal body, etc.
  • the compound 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, wettable powder, flowable agent, etc., it is usually applied after diluting with water so that the concentration of the compound of the present invention is 0.01 to 10,000 ppm. Granules, powders and the like are usually applied as they are.
  • preparations and water dilutions of the preparations may be sprayed 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.
  • the amount applied is the amount of the compound of the present invention per 1 m 2 of treatment area when treated on the surface, usually 0.01. In the case of treatment in a space, the amount of the compound of the present invention per 1 m 3 of the treatment 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 concentration of the compound of the present invention is 0.1 to 10,000 ppm. Apply oil, aerosol, smoke, poison bait, etc. as they are.
  • the pesticidal agent of the present invention When the pesticidal agent of the present invention is used for controlling ectoparasites of domestic animals such as cattle, horses, pigs, sheep, goats and chickens, and small animals such as dogs, cats, rats and mice, a method known in veterinary medicine Can be used for livestock or animals.
  • a method known in veterinary medicine Can be used for livestock or animals.
  • systemic suppression for example, administration by tablet, feed mixing, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.) is intended for non-systemic suppression.
  • a pour-on process or a spot-on process is performed by spraying an oil or an aqueous liquid.
  • 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 crops are cultivated.
  • Agricultural crops corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, buckwheat, sugar beet, rapeseed, sunflower, sugarcane, tobacco, etc.
  • Vegetables Eggplant, tomato, pepper, pepper, potato, cucumber, pumpkin, zucchini, watermelon, melon, radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, mustard, broccoli, cauliflower, burdock, sangiku, artichoke, lettuce, Leek, onion, garlic, asparagus, carrots, parsley, celery, American bowfish, spinach, chard, perilla, mint, basil, strawberry, sweet potato, yam, taro, etc.
  • Fruit trees apple, pear, Japanese pear, quince, quince, peach, plum, nectarine, ume, sweet cherry, apricot, prunes, citrus, orange, lemon, lime, grapefruit, chestnut, walnut, hazel, almond, pistachio, cashew nut, Macadamia nut, blueberry, cranberry, blackberry, raspberry, grape, oyster, olive, loquat, banana, coffee, date palm, coconut palm, oil palm, etc. Trees other than fruit trees: tea etc.
  • the crop includes a genetically modified crop.
  • the pest control agent of the present invention can be mixed or used in combination with other insecticides, acaricides, nematicides, fungicides, plant growth regulators, herbicides, synergists and safeners.
  • a part represents a weight part.
  • Formulation Example 1 9 parts of the present compound is dissolved in 37.5 parts of xylene and 37.5 parts of dimethylformamide, 10 parts of polyoxyethylene styrylphenyl ether and 6 parts of calcium dodecylbenzenesulfonate are added to this, and the mixture is stirred well. 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 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 A compound is obtained by mixing 10 parts of the compound of the present invention, 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. .
  • 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 1 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. 20 mL of the test chemical solution was sprayed on cabbage (Brassicae oleracea) at the 3-4 leaf stage. After the test chemical solution is dried, the above-ground part is cut off, stored in a polyethylene cup (capacity 100 mL) together with 5 second larvae of Pterella xylostella, stored at 25 ° C., and after 5 days, the number of surviving insects is investigated. The dead insect rate was calculated
  • required by the following formula. Death rate (%) (Number of dead insects / number of test insects) ⁇ 100 As a result, in the treatment with the compound of the present invention, the death rate was 80% or more.
  • 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. 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 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.
  • 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.

Abstract

Composé pyrimidine représenté par la formule (1), efficace en tant qu'agent de lutte contre les organismes nuisibles.
PCT/JP2016/077784 2015-09-28 2016-09-21 Composé pyrimidine et son utilisation pour la lutte contre les organismes nuisibles WO2017057121A1 (fr)

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JP2015-189359 2015-09-28
JP2015189359 2015-09-28

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WO2017057121A1 true WO2017057121A1 (fr) 2017-04-06

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Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS57176967A (en) * 1981-04-21 1982-10-30 Sankyo Co Ltd Aminopyrimidine derivative and antibacterial, insecticidal and miticidal agent
JPS63225364A (ja) * 1986-10-08 1988-09-20 Ube Ind Ltd アラルキルアミノピリミジン誘導体、その製造法並びに該誘導体を有効成分とする殺虫剤、殺ダニ剤及び殺菌剤
JPH06502864A (ja) * 1990-11-19 1994-03-31 ペン・ステイト・リサーチ・フアウンデーション 殺昆虫剤性、殺ダニ剤性および殺菌・殺カビ剤性のアミノピリミジン類
JPH07258223A (ja) * 1994-02-01 1995-10-09 Ube Ind Ltd ４−フェネチルアミノピリミジン誘導体、その製法及び農園芸用の有害生物防除剤
JPH11302261A (ja) * 1998-04-17 1999-11-02 Ube Ind Ltd ５−ヨード−４−フェネチルアミノピリミジン誘導体、その製法及び農園芸用の有害生物防除剤
WO2015146870A1 (fr) * 2014-03-28 2015-10-01 住友化学株式会社 Composé pyrimidine
JP2015189703A (ja) * 2014-03-28 2015-11-02 住友化学株式会社 ピリミジン化合物及びその有害生物防除用途
JP2015189704A (ja) * 2014-03-28 2015-11-02 住友化学株式会社 ピリミジン化合物及びその有害生物防除用途

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS57176967A (en) * 1981-04-21 1982-10-30 Sankyo Co Ltd Aminopyrimidine derivative and antibacterial, insecticidal and miticidal agent
JPS63225364A (ja) * 1986-10-08 1988-09-20 Ube Ind Ltd アラルキルアミノピリミジン誘導体、その製造法並びに該誘導体を有効成分とする殺虫剤、殺ダニ剤及び殺菌剤
JPH06502864A (ja) * 1990-11-19 1994-03-31 ペン・ステイト・リサーチ・フアウンデーション 殺昆虫剤性、殺ダニ剤性および殺菌・殺カビ剤性のアミノピリミジン類
JPH07258223A (ja) * 1994-02-01 1995-10-09 Ube Ind Ltd ４−フェネチルアミノピリミジン誘導体、その製法及び農園芸用の有害生物防除剤
JPH11302261A (ja) * 1998-04-17 1999-11-02 Ube Ind Ltd ５−ヨード−４−フェネチルアミノピリミジン誘導体、その製法及び農園芸用の有害生物防除剤
WO2015146870A1 (fr) * 2014-03-28 2015-10-01 住友化学株式会社 Composé pyrimidine
JP2015189703A (ja) * 2014-03-28 2015-11-02 住友化学株式会社 ピリミジン化合物及びその有害生物防除用途
JP2015189704A (ja) * 2014-03-28 2015-11-02 住友化学株式会社 ピリミジン化合物及びその有害生物防除用途

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