WO2003007717A1 - Method for agricultural insect pest control - Google Patents

Method for agricultural insect pest control Download PDF

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Publication number
WO2003007717A1
WO2003007717A1 PCT/JP2002/006714 JP0206714W WO03007717A1 WO 2003007717 A1 WO2003007717 A1 WO 2003007717A1 JP 0206714 W JP0206714 W JP 0206714W WO 03007717 A1 WO03007717 A1 WO 03007717A1
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Prior art keywords
compound
phenoxybenzyl
cyano
chloro
pests
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PCT/JP2002/006714
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French (fr)
Japanese (ja)
Inventor
Satoshi Nakamura
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Sumitomo Chemical Company, Limited
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Publication of WO2003007717A1 publication Critical patent/WO2003007717A1/en

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    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/541,3-Diazines; Hydrogenated 1,3-diazines

Definitions

  • the present invention relates to a method for controlling agricultural pests.
  • the present invention provides a method for controlling an agricultural pest by applying the compound (A) and a pyrethroid compound to a plant to be protected from damage by the agricultural pest or a soil where the plant is cultivated (hereinafter referred to as the present invention). Method). Further, the present invention provides an agricultural pest controlling composition containing the compound (A) and a pyrethroid compound, which is suitable for carrying out the method of the present invention.
  • Compound (A) which is one of the active ingredients in the present invention, is a compound described in U.S. Pat. No. 5,498,612, and can be produced according to the description in the publication.
  • Examples of the pyrethroid compound as one of the active ingredients in the present invention include a benzyl-type pyrethroid compound having a substituted benzyl group in the structure. More specifically, for example, 2- (4-ethoxyphenyl) _2-methylpropinole 3-phenoxybenzinole ethereol represented by the following formula:
  • the pyrethroid compound described above is a compound described in, for example, The Pesticide Manual, 12th Edition (published by The British Crop Protection Council), and can be produced by a known method, and a preparation containing the pyrethroid compound.
  • the product is commercially available.
  • the agricultural pest according to the present invention is a pest that pests plants that produce agricultural crops. Including, but not limited to, pests that attack plants grown for horticulture and plants that produce wood. Specific examples of agricultural pests include insects and nematodes as shown below.
  • Hemiptera Insects such as Lagodelphax striatellus, Nilaparvata lugens, and Singathorn fur (Sogatella furcifera), and other insects; Species, Aphis gossypii, Aphis gossypii, Myzus persicae, Orange aphid (Aphis citricola), Nisedai aphid (Lipaphis pserudobrassicae), Nippol aphid (Nippolachnus aphi) Aphids such as aphids (Toxoptera ci idius), Aphid stink bugs (Nezara antennata), and a stink bug (Plautia stall) such as a stink bug (Plautia stall) and a stink bug (Plautia stall) Whiteflies such as riorum, Benosia tabaci and Benosia argent if oli i, Bemisi
  • Lepidopteran pests Chilo suppressalis, Cnaphalocrocis medinalis, Ostrinia nubilalis, Parapediasia teterrella ⁇ Notarcha derogate ⁇ P. Japanese beetles, Spodoptera litura, Pseudaletia separata, Mamestra brassicae, Agrotis ipsilon, Trichopulcia, Heliotis, Helikoberpa, etc.
  • Diptera pests Anopheles (Delia platura), onions (Delia antiqua), etc., Flies (Liriomyza trifoli i), etc., mipales, mipayes, dwarfs.
  • Hymenopteran pests falcons such as the genus Atta, haplas such as Athalia rosae, and mifushi wasps such as Arge pagana.
  • Pteratoid pests Corn worms, such as Western corn noreworm (Diabrotica virgifera virgifera) and Southern corn noreto worm (Diabrotica undecimpunctata howardi); Coleoptera, Coleoptera (Aulacophora feraoralis), Kisujinomino, Musi doh (Phaeophyta) Chrysomelids, such as beetles (Leptinotarsa decemlineata), and Epilacunas, such as Epilachna vigintioctopunctata.
  • Corn worms such as Western corn noreworm (Diabrotica virgifera virgifera) and Southern corn noreto worm (Diabrotica undecimpunctata howardi); Coleoptera, Coleoptera (Aulacophora feraoralis), Kisujinomino, Musi doh (Phaeophyta) Chrysomelids, such as beetles (Leptin
  • Thistle pests Thrips palmi, Thrips tabaci, Thrips tabai, Thrips hawaiiensis, Thrips thrips Frankliniella occidentalis), Ponticulothrips diospyrosi.
  • Orthoptera pests Kera, putta, etc.
  • Nematodes Nematodes (Pratylenchus coffeae), Kitanegususaresenchu (Pratylenchus fallax), Cyanegusaresenchu (Pratylenchus loosi), Coleoptera japonicus (Pratylenchus vulnus), etc.
  • Cystosentieu Heterodera glycines
  • Potato cysts Globodera rostochiens is, etc., Meloidogyne hapla, Meloidogyne incognita, Aphelenchoides besseyi, Aphelenchoides besseyi, Aphelenchoides fragarieae), such as Aferencoides, Ishuku nematodes, Cinnamonidae, Pin centuries, Longidulus, Trichodnoles
  • Plants that can be protected from attack by agricultural pests by the method of the present invention include, for example, the following: Plants that produce agricultural crops, plants that are cultivated for horticulture, plants that produce wood, and the like.
  • Cereals rice, corn, wheat, oats, rye, empaku, etc.
  • Potatoes potato, sweet potato, taro, jamanoimo, etc.
  • Beans soybean, peanut, broad bean, cowpea, azuki, endo, kidney bean, etc.
  • Vegetables Solanaceous vegetables such as eggplants, tomatoes, peppers, and peppers, melons, macawuli, kiuri, shirouri, yugao, capochiya, hechima, watermelons and other vegetables, daikon, Chinese cabbage, komatsuna, bok choy, cabbage Cruciferous vegetables such as broccoli and keel, lily vegetables such as leek, onion, leek, garlic, asparagus, asteraceous vegetables such as lettuce, chisha, burdock, artichoke, carrot, celery, etc.
  • Umbelliferous vegetables such as parsley, strawberry, spinach, okra, udo, lotus root, etc.
  • Fruit trees almonds, carrots, plums, apricots, plums, nectarines, peaches, raspberries, apples, pears, vegetation, etc., mandarins, haskap, kiwifruit, papaya, mango, durian, pineapple , Banana, date palm etc.
  • Turfgrass sipa, koraisaipa, pumudagrass, bentgrass, etc.
  • Forage crops Alfalpha, Shiromekusa, Kentucky Bluegrass, Italy Mushrooms: shiitake, enokidake, maitake, oyster mushroom, etc.
  • Trees Pinaceae trees, such as larch, hinoki, cedar, beech, zelkova, drill, etc.
  • the method of the present invention is carried out by applying the compound (A) and the pyrethroid compound to the plant or the soil where the plant is grown substantially simultaneously. That is, it can be carried out by applying a mixed composition of the compound (A) and the pyrethroid compound to a plant or soil for growing a plant, or applying the compound (A) to soil for growing a plant or a plant, Further, it can be carried out by separately applying the pyrethroid compound substantially at the same time.
  • a mixed composition containing the compound (A) and a pyrethroid compound hereinafter, referred to as the present mixed composition
  • the present mixed composition a mixed composition containing the compound (A) and a pyrethroid compound
  • the ratio of the compound (A) to the pyrethroid compound used is a ratio that exhibits a synergistic effect.
  • the ratio by weight is usually 30: 1 to 1:50.
  • the ratio is preferably a ratio of 20: 1 to 1:30, and more preferably a ratio of 10: 1 to 1:20.
  • the compound (A) and the pyrethroid compound can be used in the form as they are.
  • a solid carrier, a liquid carrier and / or a gaseous carrier are added, and if necessary, an interface is added.
  • Formulated into oils, emulsions, flowables, granules, powders, aerosols, microcapsules, ULVs, sheet preparations, smokers, etc. Is done.
  • the solid carrier used in the formulation examples include clays (such as clay ore clay, diatomaceous earth, synthetic hydrated silicon oxide, bentonite, fupasami clay, acid clay), talc, ceramic, and other inorganic minerals (sericite, quartz). , Sulfur, activated carbon, calcium carbonate, hydrated silica, etc.), and fine powders and granules such as chemical fertilizers (ammonium sulfate, phosphorous ammonium, ammonium nitrate, urea, salt ammonium, etc.).
  • clays such as clay ore clay, diatomaceous earth, synthetic hydrated silicon oxide, bentonite, fupasami clay, acid clay), talc, ceramic, and other inorganic minerals (sericite, quartz).
  • fine powders and granules such as chemical fertilizers (ammonium sulfate, phosphorous ammonium, ammonium n
  • Liquid carriers include, for example, water, alcohols (methanol, ethanol, etc.), ketones (acetone, methylethyl ketone, etc.), aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, methylnaphthalene, etc.), fats Group hydrocarbons (hexane, cyclohexane, kerosene, gas oil, etc.), esters (ethyl acetate, butyl acetate, etc.), nitriles (acetonitrile, isoptyronitrile, etc.), ethers (diisopropyl ether, dioxane) Acid amides (N, N-dimethylformamide, N, N-di Examples include methylacetoamide, etc., hagenated hydrocarbons (dichloromethane, trichloroethane, carbon tetrachloride, etc.), dimethyl sulfoxide and vegetable oils
  • gaseous carrier examples include fluorocarbon, butane gas, LPG (liquefied petroleum gas), dimethyl ether and carbon dioxide gas.
  • Surfactants include, for example, alkyl sulfate esters, alkyl sulfonates, alkyl sulfonates, alkyl aryl ethers and polyalkylene ethers thereof, polyethylene glycol ethers, polyhydric alcohol esters and sugars. Alcohol derivatives are mentioned.
  • Other pharmaceutical auxiliaries include fixing agents, dispersants and stabilizers, such as casein, gelatin, polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, Saccharides, synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), PAP (isopropynole acid phosphate), BHT (2,6_di-tert-butyl_4-methylphenol), B HA (mixture of 2-tert-butynole-4-methoxyphenol and 3-tert-butyl-14-methoxyphenol), vegetable oil, mineral oil, fatty acids and fatty acid esters.
  • A) or the pyrethroid compound is usually contained in an amount of 0.01 to 90% by weight.
  • This mixture composition can be used as it is as a mixture of the compound (A) and the pyrethroid compound, but usually, as described above, a solid carrier, a liquid carrier and / or a gaseous carrier are added, and if necessary, a surfactant, Add other formulation auxiliaries and formulate into oils, emulsions, flowables, granules, powders, aerosols, microcapsules, ULVs, sheet formulations, etc. and adjust.
  • the present mixed composition can be prepared by mixing a formulation of the compound (A) with a formulation of the pyrethroid compound separately, or the compound (A) can be prepared immediately before use.
  • the ratio between the compound (A) and the pyrethroid compound is a ratio showing a synergistic effect, for example, a ratio of 30: 1 to 1:50 by weight, preferably 20: 1 to 1 by weight. : 30 ratio, more preferably 10 : 1-1: 20 ratio.
  • the total of the compound (A) and the pyrethroid compound is usually 0.01 to 90% by weight.
  • specific methods for application to plants or soil for cultivating plants include, for example, direct spraying on the aerial parts of plants, immersion or dressing of plant seeds, and application to soil for cultivating plants.
  • Surface treatment, mixing treatment, canning treatment and the like can be mentioned.
  • compound (A) and pyrethroid compound are added to feed ingredients such as cereal flour, vegetable oil, sugar, and crystalline cellulose, and if necessary, storage of antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid, and dehydroacetic acid Poisonous bait by adding food, pepper powder and other child and pet accidental food preservatives, cheese flavor, onion flavor, peanut oil and other pest-inducing flavors, which can be used to control agricultural pests. .
  • the total amount of the compound (A) and the pyrethroid compound to be applied is 0.1 to 100 g per 100 m 2 of the plant cultivation area.
  • compound (A) and pyrethroid compounds are used in the form of emulsions, wettable powders, flowables, etc., they are usually diluted with water so that the active ingredient concentration is 10 to 1000 ppm.
  • When applied in the form of granules, powders, etc. it is usually applied as it is.
  • These application rates and application concentrations vary depending on the type of formulation, application time, application place, application method, type of pest, degree of damage, etc., and can be increased or decreased without being limited to the above range. , Can be selected as appropriate.
  • a wettable powder is obtained by uniformly mixing and pulverizing with a dry mill.
  • 10% water diluent at a predetermined concentration and a water diluent at a predetermined concentration of each of the compounds (I) to (VI II) were formulated with a spreading agent (New Reno-Ion). : Manufactured by Nippon Agrochemical Co., Ltd.) so as to have a volume of 1/300000 (volume) to prepare each spray liquid.
  • cabbage was planted in plastic pots and grown until the four-leaf stage.
  • the above-mentioned spray liquid was sprayed at a rate of 30 ml per strain.
  • the cabbage leaves were released with Lepidoptera pests (five larvae of the fourth instar larva and 40 third instar larvae of the Japanese moth).
  • Lepidoptera pests five larvae of the fourth instar larva and 40 third instar larvae of the Japanese moth.
  • the degree of damage was determined by the following formula. (4 X n 4 + 3 X n 3 + 2 X n 2 + l X n 1 + OX n 0 )
  • Degree of damage (%) 100 X
  • ⁇ 4 is the number of leaves with an area ratio of 61 to 100%
  • ⁇ 3 is the number of leaves with an area of 31 to 60%
  • ⁇ 2 is the number of leaves with an area ratio of 11 to 30%
  • is the number of leaves with a 1 to 1 ⁇ % damage area
  • n Q is the number of leaves with a 0% damage area.
  • compositions of Compounds (I) to (VIII) used in the above test were 20% emulsion of Compound (I), 20% emulsion of Compound (II), and 5 of Compound (III), respectively. /. Emulsion, 10% emulsion of compound (IV), 20% emulsion of compound (V), 5% emulsion of compound (VI), 2% emulsion of compound (VII) and 6% emulsion of compound (VII I) It is.

Abstract

A method for agricultural insect pest control, which comprises applying 5-chloro-6-(1-fluoroethyl)-N-[2-[4-(trifluoromethoxy)phenyl]ethyl]pyrimidine-4-ylamine represented by the formula (A): (A) and a pyrethroid compound to a plant to be protected against the injury by an agricultural insect pest or to the soil for cultivating the plant.

Description

明 細 書  Specification
農業害虫の防除方法 技術分野 Method of controlling agricultural pests
本発明は農業害虫 (agricultural pest) の防除方法に関する。 背景技術  The present invention relates to a method for controlling agricultural pests. Background art
5 _クロロー 6— ( 1—フルォロェチル) - N - [ 2— [ 4一 (トリフノレオロメ ト キシ) フエニル] ェチル] ピリ ミジン _ 4一ィルァミンが農業害虫に対する防除活性 を有することが知られている (米国特許公報 5 , 4 9 8, 6 1 2号)。 また、 ピレス ロイド化合物が農業害虫に対する防除活性を有することも知られている (例えばザ ぺスティサイド マ二ユアノレ 第 1 2版 (The British Crop Protection Council発 行))。  5 _Chloro-6- (1-fluoroethyl) -N- [2- [4-1 (Triphnorelomethoxy) phenyl] ethyl] pyrimidine _4-ylamine is known to have a controlling activity against agricultural pests (US Patent Publications 5, 498, 612). It is also known that pyrethroid compounds have pest control activity against agricultural pests (for example, The Pesticide Manuyanore 1st Edition (published by The British Crop Protection Council)).
しかし、 これら化合物の農業害虫に対する防除活性は、 必ずしも十分ではないこと から、 より優れた農業害虫防除組成物の開発が望まれている。 発明の開示  However, since the control activity of these compounds against agricultural pests is not always sufficient, development of a more excellent agricultural pest control composition is desired. Disclosure of the invention
本発明者はかかる状況下に鋭意検討した結果、 式 (A)  The present inventor has conducted intensive studies in such a situation, and found that the formula (A)
Figure imgf000003_0001
Figure imgf000003_0001
で示される 5—クロロー 6— ( 1—フルォロェチル) — N— [ 2— [ 4 - (トリフノレ ォロメ トキシ) フエニル] ェチル] ピリ ミジン一 4一イノレアミン (以下、 化合物 (A ) と記す。) とピレスロイド化合物とを同時に使用することにより、 各々の化合物を 単独で使用した場合には防除効果が不十分な農業害虫も効果的に防除できるように なり、 結果として各々の化合物の施用薬量を低減できることを見出し、本発明を完成 した。 即ち、 本発明は、 化合物 (A) とピレスロイド化合物とを、 農業害虫による加害か ら保護しょうとする植物又はその植物を栽培する土壌に施用することによる農業害 虫の防除方法 (以下、 本発明方法と記す。) を提供する。 更に、 本発明方法を実施す るに適した、 化合物 (A) とピレスロイド化合物とを含有する農業害虫防除組成物を 提供する。 発明を実施するための最良の形態 5—chloro-6— (1-fluoroethyl) —N— [2 -— [4- (trifluoromethyl) phenyl] ethyl] pyrimidine-1-inoleamine (hereinafter referred to as compound (A)) and pyrethroid The simultaneous use of the compounds enables effective control of agricultural pests with insufficient control if each compound is used alone, resulting in a reduction in the applied dose of each compound. And completed the present invention. That is, the present invention provides a method for controlling an agricultural pest by applying the compound (A) and a pyrethroid compound to a plant to be protected from damage by the agricultural pest or a soil where the plant is cultivated (hereinafter referred to as the present invention). Method). Further, the present invention provides an agricultural pest controlling composition containing the compound (A) and a pyrethroid compound, which is suitable for carrying out the method of the present invention. BEST MODE FOR CARRYING OUT THE INVENTION
本発明における有効成分のひとつである化合物 (A) は米国特許公報 5, 498, 612号に記載された化合物であり、該公報の記載にしたがって製造することができ る。  Compound (A), which is one of the active ingredients in the present invention, is a compound described in U.S. Pat. No. 5,498,612, and can be produced according to the description in the publication.
本発明における有効成分のひとつであるピレスロイド化合物としては、例えば構造 内に置換ベンジル基を有するベンジル型ピレスロイド化合物等があげられる。 より具 体的には、 例えば下記式で示される 2— (4—エトキシフエニル) _ 2—メチルプロ ピノレ 3—フエノキシべンジノレ エーテノレ  Examples of the pyrethroid compound as one of the active ingredients in the present invention include a benzyl-type pyrethroid compound having a substituted benzyl group in the structure. More specifically, for example, 2- (4-ethoxyphenyl) _2-methylpropinole 3-phenoxybenzinole ethereol represented by the following formula:
(I)
Figure imgf000004_0001
(I)
Figure imgf000004_0001
(一般名:エトフェンプロックス、 etofenprox。 以下、 化合物(I)と記す。)、 下記式 で示される (RS) —α—シァノ一3—フエノキシベンジル (RS) -2- (4一 クロ口フエニル) —3—メチルブチレート  (Generic names: etofenprox; hereinafter, referred to as compound (I).) A compound represented by the following formula (RS) -α-cyano-13-phenoxybenzyl (RS) -2- (4-chloro) Methyl phenyl) —3-methylbutyrate
Figure imgf000004_0002
Figure imgf000004_0002
(一般名: フェンパレレート、 fenvalerate0 以下、 化合物(II)と記す。)、 下記式で 示される (S) 一 α—シァノ一3—フエノキシベンジル (S) -2- (4—クロ口 フエ二ノレ) 一3—メチルブチレート
Figure imgf000005_0001
(Generic name: fenparerate, fenvalerate 0 or less, described as compound (II).) (S) -α-cyano-13-phenoxybenzyl (S) -2- (4-chloro) represented by the following formula: Mouth Feninole) 1-3-Methylbutyrate
Figure imgf000005_0001
(一般名:エスフェンパレレート、 esfenvalerate。 以下、 化合物(III)と記す。)、 下 記式で示される (RS) —ひ一シァノ _ 3—フエノキシベンジル 2, 2, 3, 3 - テトラメチノレシク口プロパンカルボキシレート  (Generic name: esfenvalerate. Hereinafter, referred to as compound (III).), (RS) represented by the following formula: (Hiscisano_3—phenoxybenzyl 2,2,3,3-) Tetramethinoresic mouth propane carboxylate
(I )
Figure imgf000005_0002
(I)
Figure imgf000005_0002
(一般名 : フェンプロパトリン、 fenpropathrin。 以下、 化合物(IV)と記す。)、 下記 式で示ざれる 3—フエノキシベンジル (1 R S, 3 R S ; 1 R S, 3 SR) — 3— (2, 2—ジクロロビュル) 一 2, 2—ジメチルシク口プロパンカルボキシレート  (Generic names: fenpropathrin, fenpropathrin; hereinafter, referred to as compound (IV).) 3-phenoxybenzyl (1 RS, 3 RS; 1 RS, 3 SR) represented by the following formula — 3— ( 2,2-dichlorobutyl) 1,2,2-dimethylcyclopropanecarboxylate
Figure imgf000005_0003
Figure imgf000005_0003
(一般名 : レメ トリン、 permethrin0 以下、 化合物 (V)と記す。)、 下記式で示され る (RS) α—シァノ一3—フエノキシベンジル (Ζ) - (1 R S, 3RS) — 3 - (2—クロ口一 3, 3, 3—トリフロォ口プロぺニル) -2, 2—ジメチノレシク 口プロノヽ。ンカルボキシレ一ト (Generic name: remethrin, permethrin 0 or less, described as compound (V)), represented by the following formula (RS) α-cyano-13-phenoxybenzyl (Ζ)-(1 RS, 3RS) — 3-(2-chloro-1,3,3-trifluoropropenyl) -2,2-Dimethinoresic Carboxylates
Figure imgf000005_0004
Figure imgf000005_0004
(一般名 : シハロ トリン、 cyhalothrin0 以下、 化合物 (VI)と記す。)、 下記式で示さ れる 2—メチルビフエニル _ 3—ィルメチル (Z) - (1 R S, 3RS) — 3— ( 2—クロ口一 3, 3, 3—トリフルォロプロプ— 1ーェニル) 一 2, 2—ジメチルシ ク口プロパンカノレポキシレート (Generic name: cyhalothrin, cyhalothrin 0 or less, described as compound (VI).) 2-Methylbiphenyl-3-ylmethyl (Z) represented by the following formula-(1 RS, 3RS) — 3— (2-chloro 1,3,3,3-Trifluoroprop-1-enyl) 1,2,2-dimethylcy Mouth propane canolepoxylate
Figure imgf000006_0001
Figure imgf000006_0001
(—般名: ビフェントリン、 bifenthrin。 以下、 化合物 (VII)と記す。)、 下記式で示 される (RS) 一 α—シァノー 3—フエノキシベンジル (1 R S, 3RS ; 1RS , 3 SR) - 3 - (2, 2—ジクロ口ビュル) -2, 2—ジメチルシクロプロパン力 ノレボキシレート (-.. Which generic name: bifenthrin, bif en thrin hereinafter described as Compound (VII)), is shown by the following formula (RS) one α- Shiano 3- phenoxyethanol benzyl (1 RS, 3RS; 1RS, 3 SR)-3-(2,2-Dichrolic butyl) -2,2-Dimethylcyclopropane
Figure imgf000006_0002
Figure imgf000006_0002
(一般名: シペルメトリン、 cypermethrin0 以下、 化合物 (VIII)と記す。)、 下記式で 示される (S) 一 α—シァノー 3 _フエノキシベンジル (1 R, 3 S) —2, 2― ジメチノレ一 3— [2 - (2, 2, 2—トリフノレオロー 1—トリフノレオロメチノレエトキ シカルボニル) ビュル] シクロプロパンカルポキシレート (Generic name: cypermethrin, cypermethrin 0 or less, described as compound (VIII).) (S) mono-α-cyano 3 _phenoxybenzyl (1 R, 3 S) represented by the following formula: —2, 2— Dimethinole 1- [2- (2,2,2-Trifnoroleol 1-Trifnorolelomethinoleethoxycarbonyl) Bull] Cyclopropanecarboxylate
Figure imgf000006_0003
Figure imgf000006_0003
(一般名: ァクリナトリン、 acrinathrin。 以下、 化合物(IX)と記す。) 等が挙げられ る。  (Generic names: acrinathrin, hereinafter referred to as compound (IX)).
上記のピレスロイド化合物はザ ぺスティサイド マニュアル 第 1 2版 (The British Crop Protection Council発行) 等に記載されている化合物であり、 公知の 方法で製造することができ、また該ピレスロイド化合物を含有する製剤品が市販され ている。 本発明における農業害虫とは、 農作物を生産する植物を加害する害虫 (pests) 1 限らず、 園芸用に栽培される植物および木材を生産する植物を加害する害虫も含む。 農業害虫としては、 具体的には例えば以下に示されるような昆虫、 線虫等が挙げられ る。 The pyrethroid compound described above is a compound described in, for example, The Pesticide Manual, 12th Edition (published by The British Crop Protection Council), and can be produced by a known method, and a preparation containing the pyrethroid compound. The product is commercially available. The agricultural pest according to the present invention is a pest that pests plants that produce agricultural crops. Including, but not limited to, pests that attack plants grown for horticulture and plants that produce wood. Specific examples of agricultural pests include insects and nematodes as shown below.
半翅目害虫 : ヒメ トビゥンカ (Laodelphax striatellus)、 トビイロゥンカ ( Nilaparvata lugens)、 セジロウンカ (Sogatella furcifera)等のゥンカ類、 ツマ グロョコパ、ィ (Nephotettix cincticeps) , タイヮンツマグロョコノ ィ (Nephotettix virescens) 等のョコパイ類、 ヮタアブラムシ' (Aphis gossypii) , モモァカァブラ ムシ (Myzus persicae) , ミカンミ ドリアブラムシ (Aphis citricola)、 ニセダイ コンアブラムシ (Lipaphis pserudobrassicae)、 ナシミ ドリオオアブラムシ ( Nippolachnus piri)、 コミカンアブラムシ (Toxoptera aurantii) , ミカンクロア ブラムシ (Toxoptera ci idius) 等のアブラムシ類、 ァォクサカメムシ (Nezara antennata) ホソノヽリカメムシ (Cletus punctiger) , ホソヘリカメムシ (Riptortus clavetus)、 チヤバネアォカメムシ (Plautia stall) 等のカメムシ類、 オンシッコ ナンフミ (Trialeurodes vaporariorum 、 タノヽココナジフ (Bemisia tabaci)、 シノレバーリーフコナジラミ (Bemisia argent if oli i) 等のコナジラミ類、 ァカマル カイガラムシ (Aonidiella aurantii)、 サンホーゼカイガラムシ ( Corns tockasp is perniciosa)、 シトラススノースケーノレ (Unaspis citri)、 クヮシロカィガラムシ ( Pseudaulacaspis pentagona) リーブカタ刀ィガフムシ (Saissetia o丄 eae)、 5. カンノフ J 力 刀フムシ (Lepiaosaphes beckii)、 ノレヒーロウムン (Ceroplastes rubens)、 イセリャカイガラムシ (Icerya purchasi) 等のカイガラムシ類、 グンパ ィムシ類、 キジラミ類等。  Hemiptera: Insects such as Lagodelphax striatellus, Nilaparvata lugens, and Singathorn fur (Sogatella furcifera), and other insects; Species, Aphis gossypii, Aphis gossypii, Myzus persicae, Orange aphid (Aphis citricola), Nisedai aphid (Lipaphis pserudobrassicae), Nippol aphid (Nippolachnus aphi) Aphids such as aphids (Toxoptera ci idius), Aphid stink bugs (Nezara antennata), and a stink bug (Plautia stall) such as a stink bug (Plautia stall) and a stink bug (Plautia stall) Whiteflies such as riorum, Benosia tabaci and Benosia argent if oli i, Bemisia argent if oli i; Aonidiella aurantii; ), Pseudaulacaspis pentagona, Pseudaulacaspis pentagona, Saissetia o 丄 eae, 5. Kannoff J, Lepiaosaphes beckii, Ceroplastes rubens, and Icerya purpura, etc. , Beetles, lice, etc.
鱗翅目害虫:二カメィガ (Chilo suppressalis) , コブノメイガ (Cnaphalocrocis medinalis) , ョ一口ビアンコーンポーラ一 (Ostrinia nubilalis)、 シパットガ ( Parapediasia teterrella) ^ ヮタノメ カ (Notarcha derogate) ^ ノシメマダフメ ィガ(Plodia interpunctella)等のメイガ類、ハスモンョトウ(Spodoptera litura )、 ァヮョ 卜ゥ (Pseudaletia separata)、 ョ卜ゥ (Mamestra brassicae)、 タマ ナヤガ (Agrotis ipsilon)、 トリコプルシア属、 へリオティス属、 へリコべルパ属 等のャガ類、 モンシロチョウ (Pieris rapae) 等のシロチョウ類、 アドキソフイエ ス属、 ナシヒメシンクイ (Grapholita molesta) , コドリンガ (Cydia pomonella) 等のハマキガ類、 モモシンクィガ (Carposina niponensis) 等のシンクィガ類、 リ ォネティア属等のハモグリガ類、 リマントリァ属、 ユープロクティス属等のドクガ類 、 コナガ (Plutella xylostella) 等のスガ類、 ヮタァカミムシ (Pectinophora gossypiella) 等のキパガ類、 アメリカシロヒ トリ (Hyphantria cunea) 等のヒ トリ ガ類等。 Lepidopteran pests: Chilo suppressalis, Cnaphalocrocis medinalis, Ostrinia nubilalis, Parapediasia teterrella ^ Notarcha derogate ^ P. Japanese beetles, Spodoptera litura, Pseudaletia separata, Mamestra brassicae, Agrotis ipsilon, Trichopulcia, Heliotis, Helikoberpa, etc. , Pieris rapae and other white butterflies, Adoxofuses, Papilioita molesta, Codlinga (Cydia pomonella) And squirrels such as the locust (Carposina niponensis), the lycopodium such as the genus Rionetia, the toads such as the genus Limantria and the genus Euproctis, the stags and the like (Pectinophora gossypia) such as Plutella xylostella And other birds such as American white chicks (Hyphantria cunea).
双翅目害虫: タネバエ (Delia platura)、 タマネギパェ (Delia antiqua) 等の ハナバエ類、 マメハモグリバエ (Liriomyza trifoli i) 等のハモグリバエ類、 ミパ ェ類、 ショウジョゥパェ類等。  Diptera pests: Anopheles (Delia platura), onions (Delia antiqua), etc., Flies (Liriomyza trifoli i), etc., mipales, mipayes, dwarfs.
膜翅目害虫:アツタ属等のァリ類、 力ブラハパチ (Athalia rosae) 等のハパチ類 、 チュウレンジハパチ (Arge pagana) 等のミフシハパチ類等。  Hymenopteran pests: falcons such as the genus Atta, haplas such as Athalia rosae, and mifushi wasps such as Arge pagana.
雜翅目害虫:ウェスタンコーンノレームワーム (Diabrotica virgifera virgifera )、 サザンコーンノレートワーム (Diabrotica undecimpunctata howardi) 等のコー ンノレートワーム類、 ドウガネブイブイ (Anomala cuprea)、 ヒメコガネ (Anomala rufocuprea) 等のコガネムシ類、 メイズウイ一ビル (Sitophilus zearaais)、 イネミ ズゾゥムシ (Lissorhoptrus oryzophilus)、 ァノレファノレフアタコゾゥムシ (Hypera pastica) 等の、ノクムシ類、 クリノヽムシ (Aulacophora feraoralis) , キスジノミノ、ム シ (Phyllotreta strioiata)、 コロフドノヽムシ (Leptinotarsa decemlineata) 等 のハムシ類、 ニジユウャホシテントウ (Epilachna vigintioctopunctata) 等のェピ ラクナ類等。  Pteratoid pests: Corn worms, such as Western corn noreworm (Diabrotica virgifera virgifera) and Southern corn noreto worm (Diabrotica undecimpunctata howardi); Coleoptera, Coleoptera (Aulacophora feraoralis), Kisujinomino, Musi doh (Phaeophyta) Chrysomelids, such as beetles (Leptinotarsa decemlineata), and Epilacunas, such as Epilachna vigintioctopunctata.
ァザミゥマ目害虫: ミナミキイロアザミゥマ (Thrips palmi) , ネギアザミゥマ ( Thrips tabaci) , ハナァザミゥマ (Thrips hawaiiensis)、 チヤノキイロアザミゥ マ (Scirtothrips dorsalis)、 ヒラズノヽナァザミゥマ (Frankliniella intonsa、 ミ力ンキイ口ァザミゥマ (Frankliniella occidentalis)、 力キクダァザミゥマ ( Ponticulothrips diospyrosi 。  Thistle pests: Thrips palmi, Thrips tabaci, Thrips tabai, Thrips hawaiiensis, Thrips thrips Frankliniella occidentalis), Ponticulothrips diospyrosi.
直翅目害虫:ケラ類、 パッタ類等。  Orthoptera pests: Kera, putta, etc.
線虫類: ミナミネグサレセンチュゥ (Pratylenchus coffeae)、 キタネグサレセン チュウ (Pratylenchus fallax)、 チヤネグサレセンチュゥ (Pratylenchus loosi) 、 クノレミネグサレセンチユウ (Pratylenchus vulnus) 等のネグサレセンチユウ類、 ダイズシストセンチユウ (Heterodera glycines) , ジャガイモシストセンチユウ ( Globodera rostochiens is) 等のシス トセンチユウ類、 キタネコブセンチユウ ( Meloidogyne hapla)、 サッマイモネコフセンチユウ (Meloidogyne incognita) 等 のネコブセンチユウ類、 イネシンガレセンチユウ (Aphelenchoides besseyi)、 イチ ゴセンチユウ (Aphelenchoides fragarieae) 等のァフェレンコイデス類、 イシュク センチュゥ類、 ヮセンチユウ類、 ピンセンチュゥ類、 ロンギドルス類、 トリコドノレス 本発明方法により、 農業害虫による加害から保護することのできる植物としては、 例えば以下に示されるような農作物を生産する植物、 園芸用に栽培される植物および 木材を生産する植物等があげられる。 Nematodes: Nematodes (Pratylenchus coffeae), Kitanegususaresenchu (Pratylenchus fallax), Cyanegusaresenchu (Pratylenchus loosi), Coleoptera japonicus (Pratylenchus vulnus), etc. Cystosentieu (Heterodera glycines), Potato cysts Globodera rostochiens is, etc., Meloidogyne hapla, Meloidogyne incognita, Aphelenchoides besseyi, Aphelenchoides besseyi, Aphelenchoides fragarieae), such as Aferencoides, Ishuku nematodes, Cinnamonidae, Pin centuries, Longidulus, Trichodnoles Plants that can be protected from attack by agricultural pests by the method of the present invention include, for example, the following: Plants that produce agricultural crops, plants that are cultivated for horticulture, plants that produce wood, and the like.
穀物類:イネ、 トウモロコシ、 コムギ、 ォォムギ、 ライムギ、 ェンパク等。  Cereals: rice, corn, wheat, oats, rye, empaku, etc.
いも類:パレイショ、 カンショ、 サトイモ、 ャマノィモ等。  Potatoes: potato, sweet potato, taro, jamanoimo, etc.
まめ類:ダイズ、 ラッカセィ、 ソラマメ、 ササゲ、 ァズキ、 エンドゥ、 インゲンマ メ等。  Beans: soybean, peanut, broad bean, cowpea, azuki, endo, kidney bean, etc.
野菜類:ナス、 トマト、 ピーマン、 トウガラシ等のナス科野菜、 メロン、 マクワウ リ、 キユウリ、 シロウリ、 ユウガオ、 カポチヤ、 へチマ、 スイカ等のゥリ科野菜、 ダ イコン、 ハクサイ、 コマツナ、 チンゲンサイ、 キャベツ、 ブロッコリ一、 ケ一ル等の アブラナ科野菜、 ネギ、 タマネギ、 ニラ、 ニン-ク、 アスパラガス等のユリ科野菜、 レタス、 チシャ、 ゴボウ、 ァーティーチョ一ク等のキク科野菜、 ニンジン、 セルリー 、 パセリ等のセリ科野菜、 イチゴ、 ホウレンソゥ、 オクラ、 ウド、 レンコン等。 果樹類:ァ—モンド、 ォゥトウ、 ウメ、 アンズ、 スモモ、 ネクタリン、 モモ、 キイ チゴ類、 リンゴ、 ナシ、 ビヮ等のパラ科、 ミカン類、 ハスカップ、 キウイフルーツ、 パパイヤ、 マンゴー、 ドリアン、 パインアップル、 バナナ、 ナツメヤシ等。  Vegetables: Solanaceous vegetables such as eggplants, tomatoes, peppers, and peppers, melons, macawuli, kiuri, shirouri, yugao, capochiya, hechima, watermelons and other vegetables, daikon, Chinese cabbage, komatsuna, bok choy, cabbage Cruciferous vegetables such as broccoli and keel, lily vegetables such as leek, onion, leek, garlic, asparagus, asteraceous vegetables such as lettuce, chisha, burdock, artichoke, carrot, celery, etc. Umbelliferous vegetables such as parsley, strawberry, spinach, okra, udo, lotus root, etc. Fruit trees: almonds, carrots, plums, apricots, plums, nectarines, peaches, raspberries, apples, pears, vegetation, etc., mandarins, haskap, kiwifruit, papaya, mango, durian, pineapple , Banana, date palm etc.
特用作物:チヤ、 タバコ、 コーヒー、 サトウキビ、 テンサイ、 ォリーブ、 ヮタ、 ィ グサ、 ヒマヮリ、 ナタネ、 ソパ、 コンニヤク、 チョゥセンニンジン等。  Special crops: cherries, tobacco, coffee, sugarcane, sugar beet, olive, ivy, rush, castor bean, rapeseed, sopa, konnyaku, and chopped carrot.
花卉 ·花木類:キク類、 ユリ類、 パラ類、 カーネーション、 トルコギキヨウ、 スト ック、 ッッジ類、 ポインセチア等。  Flowers and flowers: chrysanthemums, lilies, paras, carnations, lisianthus, stocks, rugs, poinsettia, etc.
芝草類:シパ、 コゥライシパ、 パミューダグラス、 ベントグラス等。  Turfgrass: sipa, koraisaipa, pumudagrass, bentgrass, etc.
飼料作物:アルフアルファ、 シロッメクサ、 ケンタツキ一ブルーグラス、 イタリア キノコ類:シィタケ、 エノキダケ、 マイタケ、 ヒラタケ等。 Forage crops: Alfalpha, Shiromekusa, Kentucky Bluegrass, Italy Mushrooms: shiitake, enokidake, maitake, oyster mushroom, etc.
樹木類:カラマツ等のマツ科樹木、 ヒノキ、 スギ、 ブナ、 ケャキ、 キリ等。  Trees: Pinaceae trees, such as larch, hinoki, cedar, beech, zelkova, drill, etc.
本発明方法は、 化合物 (A) とピレスロイ ド化合物とを、 実質的に同時期に植物又 は植物を栽培する土壌に施用することにより行われる。 即ち、 化合物 (A) とピレス ロイド化合物との混合組成物を植物又は植物を栽培する土壌に施用することにより 行うこともできるし、 化合物 (A) を植物又は植物を栽培する土壌に施用し、 更にピ レスロイド化合物を実質的に同時期に別途施用することによつても行うことができ る。 但し、 通常は施用作業の簡便性等から、 化合物 (A) とピレスロイド化合物とを 含有する混合組成物 (以下、 本混合組成物と記す。) を使用する。  The method of the present invention is carried out by applying the compound (A) and the pyrethroid compound to the plant or the soil where the plant is grown substantially simultaneously. That is, it can be carried out by applying a mixed composition of the compound (A) and the pyrethroid compound to a plant or soil for growing a plant, or applying the compound (A) to soil for growing a plant or a plant, Further, it can be carried out by separately applying the pyrethroid compound substantially at the same time. However, a mixed composition containing the compound (A) and a pyrethroid compound (hereinafter, referred to as the present mixed composition) is usually used for the convenience of application.
本発明方法において、 使用する化合物 (A) とピレスロイド化合物との割合は、 相 乗的な効果を示す割合であるが、 具体的には例えば重量比で通常 3 0 : 1 - 1 : 5 0 の割合、 好ましくは 2 0 : 1〜 1 : 3 0の割合、 さらに好ましくは 1 0 : 1〜 1 : 2 0の割合である。  In the method of the present invention, the ratio of the compound (A) to the pyrethroid compound used is a ratio that exhibits a synergistic effect. Specifically, for example, the ratio by weight is usually 30: 1 to 1:50. The ratio is preferably a ratio of 20: 1 to 1:30, and more preferably a ratio of 10: 1 to 1:20.
本発明方法を実施するにおいて、 化合物 (A) およびピレスロイド化合物は、 その ままの形態で使用することも可能である力 通常は固体担体、 液体担体及び/又はガ ス状担体を加え、 必要により界面活性剤、 その他の製剤用補助剤を添加して、 油剤、 乳剤、 フロアブル剤、 粒剤、 粉剤、 エアゾール、 マイクロカプセル剤、 U L V剤、 シ ート製剤、 燻煙剤等に製剤化されて使用される。  In carrying out the method of the present invention, the compound (A) and the pyrethroid compound can be used in the form as they are. Usually, a solid carrier, a liquid carrier and / or a gaseous carrier are added, and if necessary, an interface is added. Formulated into oils, emulsions, flowables, granules, powders, aerosols, microcapsules, ULVs, sheet preparations, smokers, etc. Is done.
製剤化の際に用いられる固体担体としては、 例えば粘土類 (力オリンクレー、 珪藻 土、 合成含水酸化珪素、 ベントナイト、 フパサミクレー、 酸性白土等)、 タルク、 セ ラミック、 その他の無機鉱物 (セリサイト、 石英、 硫黄、 活性炭、 炭酸カルシウム、 水和シリカ等)、 化学肥料 (硫安、 燐安、 硝安、 尿素、 塩安等) 等の微粉末及び粒状 物等があげられる。  Examples of the solid carrier used in the formulation include clays (such as clay ore clay, diatomaceous earth, synthetic hydrated silicon oxide, bentonite, fupasami clay, acid clay), talc, ceramic, and other inorganic minerals (sericite, quartz). , Sulfur, activated carbon, calcium carbonate, hydrated silica, etc.), and fine powders and granules such as chemical fertilizers (ammonium sulfate, phosphorous ammonium, ammonium nitrate, urea, salt ammonium, etc.).
液体担体としては、 例えば水、 アルコール類 (メタノール、 エタノール等)、 ケト ン類 (アセトン、 メチルェチルケトン等)、 芳香族炭化水素類 (ベンゼン、 トルエン 、 キシレン、 ェチルベンゼン、 メチルナフタレン等)、 脂肪族炭化水素類 (へキサン 、 シクロへキサン、 灯油、 軽油等)、 エステル類 (酢酸ェチル、 酢酸プチル等)、 ニト リル類 (ァセトニトリル、 イソプチロニトリル等)、 エーテル類 (ジイソプロピルェ 一テル、 ジォキサン等)、 酸アミド類 (N, N—ジメチルホルムアミド、 N, N—ジ メチルァセトアミ ド等)、 ハ口ゲン化炭化水素類 (ジクロロメタン、 トリクロ口エタ ン、 四塩化炭素等)、 ジメチルスルホキシド及び植物油 (大豆油、 綿実油等) があげ られる。 Liquid carriers include, for example, water, alcohols (methanol, ethanol, etc.), ketones (acetone, methylethyl ketone, etc.), aromatic hydrocarbons (benzene, toluene, xylene, ethylbenzene, methylnaphthalene, etc.), fats Group hydrocarbons (hexane, cyclohexane, kerosene, gas oil, etc.), esters (ethyl acetate, butyl acetate, etc.), nitriles (acetonitrile, isoptyronitrile, etc.), ethers (diisopropyl ether, dioxane) Acid amides (N, N-dimethylformamide, N, N-di Examples include methylacetoamide, etc., hagenated hydrocarbons (dichloromethane, trichloroethane, carbon tetrachloride, etc.), dimethyl sulfoxide and vegetable oils (soybean oil, cottonseed oil, etc.).
ガス状担体としては、 例えばフルォロカーボン、 ブタンガス、 L P G (液化石油ガ ス)、 ジメチルエーテル及び炭酸ガスがあげられる。  Examples of the gaseous carrier include fluorocarbon, butane gas, LPG (liquefied petroleum gas), dimethyl ether and carbon dioxide gas.
界面活性剤としては、 例えばアルキル硫酸エステノレ塩、 アルキルスルホン酸塩、 ァ ルキルァリ一ルスルホン酸塩、アルキルァリールエーテル類及びそのポリ才キシェチ レン化物、 ポリエチレングリコールエーテル類、 多価アルコールエステノレ類並びに糖 アルコール誘導体があげられる。  Surfactants include, for example, alkyl sulfate esters, alkyl sulfonates, alkyl sulfonates, alkyl aryl ethers and polyalkylene ethers thereof, polyethylene glycol ethers, polyhydric alcohol esters and sugars. Alcohol derivatives are mentioned.
その他の製剤用補助剤としては、 固着剤、 分散剤及び安定剤等、 具体的には例えば カゼイン、 ゼラチン、 多糖類 (でんぷん、 アラビアガム、 セルロース誘導体、 アルギ ン酸等)、 リグニン誘導体、 ベントナイト、 糖類、 合成水溶性高分子 (ポリビニルァ ルコール、 ポリビニルピロリ ドン、 ポリアクリル酸類等)、 P A P (酸性りん酸ィソ プロピノレ)、 B H T ( 2, 6 _ジ一 tert—ブチル _ 4 _メチルフエノール)、 B HA ( 2—tert—ブチノレ— 4—メ トキシフエノールと 3—tert—ブチル一 4ーメ トキシフ エノールとの混合物)、 植物油、 鉱物油、 脂肪酸及び脂肪酸エステル等があげられる これらの製剤において、 化合物 (A) またはピレスロイド化合物は、 通常 0 . 0 1 〜 9 0重量%含有される。  Other pharmaceutical auxiliaries include fixing agents, dispersants and stabilizers, such as casein, gelatin, polysaccharides (starch, gum arabic, cellulose derivatives, alginic acid, etc.), lignin derivatives, bentonite, Saccharides, synthetic water-soluble polymers (polyvinyl alcohol, polyvinylpyrrolidone, polyacrylic acids, etc.), PAP (isopropynole acid phosphate), BHT (2,6_di-tert-butyl_4-methylphenol), B HA (mixture of 2-tert-butynole-4-methoxyphenol and 3-tert-butyl-14-methoxyphenol), vegetable oil, mineral oil, fatty acids and fatty acid esters. A) or the pyrethroid compound is usually contained in an amount of 0.01 to 90% by weight.
本混合組成物は、 化合物 (A) とピレスロイド化合物の混合物のそのままでも可能 であるが、 通常は上記のように、 固体担体、 液体担体及び/又はガス状担体を加え、 必要により界面活性剤、 その他の製剤用補助剤を添加して、 油剤、 乳剤、 フロアブル 剤、 粒剤、 粉剤、 エアゾール、 マイクロカプセル剤、 U L V剤、 シート製剤等に製剤 化して調整する。 また、 本混合組成物は化合物 (A) を製剤化したものとピレスロイ ド化合物を別途製剤化したものとを混合することにより調製することもできるし、 ま た、 使用直前に化合物 (A) の製剤の希釈液とピレスロイ ド化合物の製剤の希釈液と を混合することにより調製することもできる。 本混合組成物において、 化合物 (A) とピレスロイド化合物との割合は、 相乗的な効果を示す割合、 例えば重量比で 3 0 : 1〜 1 : 5 0の割合、 好ましくは 2 0 : 1〜 1 : 3 0の割合、 さらに好ましくは 1 0 : 1 - 1 : 2 0の割合である。 本混合組成物において、 化合物 (A) とピレスロイド 化合物との合計は、 通常 0 . 0 1〜9 0重量%でぁる。 This mixture composition can be used as it is as a mixture of the compound (A) and the pyrethroid compound, but usually, as described above, a solid carrier, a liquid carrier and / or a gaseous carrier are added, and if necessary, a surfactant, Add other formulation auxiliaries and formulate into oils, emulsions, flowables, granules, powders, aerosols, microcapsules, ULVs, sheet formulations, etc. and adjust. In addition, the present mixed composition can be prepared by mixing a formulation of the compound (A) with a formulation of the pyrethroid compound separately, or the compound (A) can be prepared immediately before use. It can also be prepared by mixing a diluent of a preparation and a diluent of a preparation of a pyrethroid compound. In the present mixed composition, the ratio between the compound (A) and the pyrethroid compound is a ratio showing a synergistic effect, for example, a ratio of 30: 1 to 1:50 by weight, preferably 20: 1 to 1 by weight. : 30 ratio, more preferably 10 : 1-1: 20 ratio. In the present mixed composition, the total of the compound (A) and the pyrethroid compound is usually 0.01 to 90% by weight.
本発明方法において、植物又は植物を栽培する土壌に施用する具体的な方法として は、例えば植物の地上部への直接散布、 植物の種子の浸漬処理又は粉衣処理、 植物を 栽培する土壌への表面処理、 混和処理、 かん注処理等が挙げられる。  In the method of the present invention, specific methods for application to plants or soil for cultivating plants include, for example, direct spraying on the aerial parts of plants, immersion or dressing of plant seeds, and application to soil for cultivating plants. Surface treatment, mixing treatment, canning treatment and the like can be mentioned.
また、 穀物粉、 植物油、 糖、 結晶セルロース等の餌成分に、 化合物 (A) とピレス ロイド化合物とを加え、 更に必要によりジブチルヒドロキシトルエン、 ノルジヒドロ グアイァレチン酸等の酸化防止剤、 デヒドロ酢酸等の保存料、 トウガラシ粉末等の子 どもやペットによる誤食防止剤、 チーズ香料、 タマネギ香料、 ピーナッツオイルなど の害虫誘引性香料等を加えて毒餌とし、 これを用いて農業害虫を防除することもでき る。  In addition, compound (A) and pyrethroid compound are added to feed ingredients such as cereal flour, vegetable oil, sugar, and crystalline cellulose, and if necessary, storage of antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid, and dehydroacetic acid Poisonous bait by adding food, pepper powder and other child and pet accidental food preservatives, cheese flavor, onion flavor, peanut oil and other pest-inducing flavors, which can be used to control agricultural pests. .
本発明方法において、 施用する化合物 (A) とピレスロイド化合物との合計量は、 植物の栽培面積 1 0 0 0 m2あたり、 0 . 1〜1 0 0 0 gである。 化合物 (A) およ びピレスロイド化合物を、 乳剤、 水和剤、 フロアブル剤等の製剤形態にて用いる場合 は通常、有効成分濃度が 1 0〜1 0 0 0 0 p p mとなるように水で希釈した後に施用 し、 粒剤、 粉剤等の製剤にて施用する場合は通常、 そのままの形態で施用する。 これ らの施用量および施用濃度は、 製剤の種類、 施用時期、 施用場所、 施用方法、 害虫の 種類、 被害程度等の状況によって異なり、 上記の範囲に限定されることなく増減させ ることができ、 適宜選択することができる。 In the method of the present invention, the total amount of the compound (A) and the pyrethroid compound to be applied is 0.1 to 100 g per 100 m 2 of the plant cultivation area. When compound (A) and pyrethroid compounds are used in the form of emulsions, wettable powders, flowables, etc., they are usually diluted with water so that the active ingredient concentration is 10 to 1000 ppm. When applied in the form of granules, powders, etc., it is usually applied as it is. These application rates and application concentrations vary depending on the type of formulation, application time, application place, application method, type of pest, degree of damage, etc., and can be increased or decreased without being limited to the above range. , Can be selected as appropriate.
本発明方法においては、 化合物 (A) およびピレスロイド化合物以外に、 他の殺虫 剤、 殺線虫剤等と共に使用することもできる。 本発明を本混合組成物の製剤例および本発明方法の実施例によりさらに詳しく説 明するが、 本発明はこれらの例に限定されるものではない。  In the method of the present invention, in addition to the compound (A) and the pyrethroid compound, it can be used together with other insecticides, nematicides and the like. The present invention will be described in more detail with reference to Formulation Examples of the present mixed composition and Examples of the method of the present invention, but the present invention is not limited to these Examples.
まず、 本混合組成物の製剤例を示す。 なお、 部は重量部を表す。  First, a formulation example of the present mixed composition will be described. In addition, parts represent parts by weight.
製剤例 1 Formulation Example 1
化合物 (A) 5部、 化合物(I)〜(IX)のいずれかを 5 0部、 ポリオキシエチレンス チリルフエニルエーテル 8部、 ドデシルベンゼンスルホン酸カルシウム 2部およびキ シレン 3 5部を均一に混合して乳剤を得る。 製剤例 2 5 parts of compound (A), 50 parts of any of compounds (I) to (IX), 8 parts of polyoxyethylenestyrylphenyl ether, 2 parts of calcium dodecylbenzenesulfonate and 35 parts of xylene were uniformly mixed. Mix to obtain an emulsion. Formulation Example 2
化合物 (A) 4部、 化合物(I)〜(IX)のいずれか 2 0部、 ドデシルベンゼンスルホ ン酸ナトリウム 3部、 リグ二ンスルホン酸ナトリウム 3部およびおよび硅藻土 7 0部 をジヱットエアーミルで均一に混合粉砕して水和剤を得る。  4 parts of compound (A), 20 parts of any of compounds (I) to (IX), 3 parts of sodium dodecylbenzenesulfonate, 3 parts of sodium ligninsulfonate and 70 parts of diatomaceous earth A wettable powder is obtained by uniformly mixing and pulverizing with a dry mill.
製剤例 3 Formulation Example 3
化合物 (A) を 0 · 5部、 化合物(I)〜(IX)のいずれか 1部、 タノレク 4 8 . 5部お よびクレー 5 0部を均一に混合粉碎して粉剤を得る。  0.5 parts of compound (A), 1 part of any of compounds (I) to (IX), 48.5 parts of Tanolek and 50 parts of clay are uniformly mixed and ground to obtain a powder.
製剤例 4 ' Formulation Example 4 '
化合物 (A) 1 0部、 化合物( I )〜( IX)のいずれか 5部にドデシルべンゼンスルホ ン酸ナトリウム 5部、 ベントナイト 3 0部およびクレー 5 0部を加え、 充分攪拌混合 する。 次いで、 これらの混合物に適量の水を加え、 さらに攪拌し、 造粒機で製粒し、 通風乾燥して粒剤を得る。  To 10 parts of the compound (A) and 5 parts of any of the compounds (I) to (IX), 5 parts of sodium dodecylbenzenesensulfonate, 30 parts of bentonite and 50 parts of clay are added, and the mixture is thoroughly stirred and mixed. Next, an appropriate amount of water is added to the mixture, and the mixture is further stirred, granulated by a granulator, and dried by ventilation to obtain granules.
製剤例 5 Formulation Example 5
ポリオキシエチレンスチリルフエ二ルェ一テルサルフエ一ト塩 5部、 1 %ザンサン ガム水溶液 2 0部、 スメクタイト系鉱物 3部および水 5 7部を均一に溶解し、化合物 (A) 5部、 化合物(I)〜(IX)のいずれか 1 0部を加えてよく攪拌した後、 サンドミ ルにて湿式粉碎してフ口アプル剤を得る。  5 parts of polyoxyethylene styrylphenyl tersulfate salt, 20 parts of a 1% xanthan gum aqueous solution, 3 parts of smectite mineral and 57 parts of water were uniformly dissolved, and 5 parts of compound (A), compound (I) ) To (IX), add well, stir well, and wet-pulverize with a sand mill to obtain a mouthful.
次に本発明方法の実施例を示す。  Next, examples of the method of the present invention will be described.
実施例 Example
化合物 (A) の 1 0 %水和剤の所定濃度の水希釈液に、 化合物(Ι)〜(ΉΙΙ)のそれ ぞれの製剤を所定濃度となるように加えた水希釈液、 化合物 (Α) 1 0 %水和剤の所 定濃度の水希釈液、 及び化合物( I )〜 (VI II )のそれぞれの製剤の所定濃度の水希釈液 の各々に対して、 展着剤 (新リノ一:日本農薬株式会社製) を 1 / 3 0 0 0 (容量) となるように加え、 各々の散布液を調製した。  A water diluent obtained by adding each of the preparations of Compounds (II) to (III) to a predetermined concentration in a water diluent of 10% wettable powder of compound (A) at a predetermined concentration. ) 10% water diluent at a predetermined concentration and a water diluent at a predetermined concentration of each of the compounds (I) to (VI II) were formulated with a spreading agent (New Reno-Ion). : Manufactured by Nippon Agrochemical Co., Ltd.) so as to have a volume of 1/300000 (volume) to prepare each spray liquid.
一方、 プラスチックポットにキャベツを植え、 4葉期まで生育させた。 ここに、 上 記散布液を、 1株あたり 3 0 m lの割合で散布した。 風乾後、 そのキャベツの葉に鱗 翅目害虫 (ハスモンョトウ 4齢幼虫 5頭とコナガ 3齢幼虫 4 0頭) を放した。 散布 3 日後に、 キャベツの葉の食害面積を調査し、 下式により食害度を求めた。 (4 X n4 + 3 X n3 + 2 X n2 + l X n1 + O X n0) 食害度 (%) = 100 X On the other hand, cabbage was planted in plastic pots and grown until the four-leaf stage. Here, the above-mentioned spray liquid was sprayed at a rate of 30 ml per strain. After air drying, the cabbage leaves were released with Lepidoptera pests (five larvae of the fourth instar larva and 40 third instar larvae of the Japanese moth). Three days after spraying, the area affected by cabbage leaves was investigated, and the degree of damage was determined by the following formula. (4 X n 4 + 3 X n 3 + 2 X n 2 + l X n 1 + OX n 0 ) Degree of damage (%) = 100 X
4 X (,η4 + η3 + η2 + η1 + η0) 4 X (, η 4 + η 3 + η 2 + η 1 + η 0 )
(式中、 η4は食害面積率が 61〜 100 %の葉数、 η3は食害面積率が 31〜 6 0 %の葉数、 η2は食害面積率が 11〜 30 %の葉数、 ηιは食害面積率が 1〜 1◦ % の葉数及び nQは食害面積率が 0 %の葉数を表す。) (In the formula, η 4 is the number of leaves with an area ratio of 61 to 100%, η 3 is the number of leaves with an area of 31 to 60%, η 2 is the number of leaves with an area ratio of 11 to 30%, ηι is the number of leaves with a 1 to 1◦% damage area, and n Q is the number of leaves with a 0% damage area.)
なお、 上記試験にて用いた化合物(I)〜(VIII)の製剤はそれぞれ、 化合物(I)の 20 %乳剤、 化合物( II )の 20 %乳剤、 化合物( Π I )の 5。/。乳剤、 化合物( IV)の 10 %乳 剤、 化合物 (V)の 20%乳剤、 化合物 (VI)の 5%乳剤、 化合物 (VII)の 2%乳剤及び化 合物 (VII I )の 6 %乳剤である。  The preparations of Compounds (I) to (VIII) used in the above test were 20% emulsion of Compound (I), 20% emulsion of Compound (II), and 5 of Compound (III), respectively. /. Emulsion, 10% emulsion of compound (IV), 20% emulsion of compound (V), 5% emulsion of compound (VI), 2% emulsion of compound (VII) and 6% emulsion of compound (VII I) It is.
結果を表 1に示す。 Table 1 shows the results.
ィ匕合物名 有効成分濃度 食害度 Name of the active ingredient Concentration of damage
Ρ ρ πυ (%)  Ρ ρ πυ (%)
化合物 κΑ) iD 75  Compound κΑ) iD 75
化合物 ( I ) 50 1 00  Compound (I) 50 1 00
化合物 (I I) 5 87. 5  Compound (II) 5 87.5
化合物 (I I I) 5 1 00  Compound (I I I) 5 1 00
化合物 ( I V) 5 1 00  Compound (IV) 5 1 00
化合物 (V) 5 0 1 00  Compound (V) 5 0 1 00
化合物 (V I ) 5 8 7. 5  Compound (V I) 5 8 7.5
化合物 (V I I) 5 1 00  Compound (V I I) 5 1 00
化合物 (V I I I ) 5 1 00  Compound (V I I I) 5 100
化合物 (A) +化合物 (I) 5 + 50 0  Compound (A) + Compound (I) 5 + 500
化合物 (A) +化合物 (I I) 5 + 5 25  Compound (A) + Compound (II) 5 + 5 25
化合物 (A) +化合物 (I I I) 5 + 5 0  Compound (A) + Compound (I I I) 5 + 50
化合物 (A) +化合物 ( I V) 5 + 5 1 2. 5  Compound (A) + Compound (IV) 5 + 5 12.5
化合物 (A; +ィ匕合物 (V; 5 + 5 0 1 2. 5  Compound (A; +
化合物 (A) +化合物 (V I ) 5 + 5 0  Compound (A) + Compound (V I) 5 + 50
化合物 (A) +化合物 (V I I ) 5 + 5 1 2. 5  Compound (A) + Compound (V I I) 5 + 5 12.5
化合物 (A) +化合物 (V I I I) 5 + 5 0  Compound (A) + Compound (V I I) 5 + 50
無処理 1 00 産業上の利用可能性  No treatment 1 00 Industrial applicability
本発明によれば、 農業害虫を効果的に防除することが可能であり、植物を農業害虫 による加害から保護することができる。  ADVANTAGE OF THE INVENTION According to this invention, it is possible to control agricultural pests effectively and to protect a plant from damage by agricultural pests.

Claims

請 求 の 範 囲  The scope of the claims
Figure imgf000016_0001
Figure imgf000016_0001
で示される 5—クロロー 6— (1一フルォロェチル) -N- [2— [4一 (トリフノレ ォロメ トキシ) フエニル] ェチル] ピリミジン一 4一ィルァミンとピレスロイド化合 物との有効量を植物又はその植物を栽培する土壌に施用することによる、該植物を加 害する農業害虫を防除する方法。 2. 式 (A) で示される 5—クロロー 6— (1 --フルォロェチル) 一 N— [2 - [4一 (トリフルォロメ トキシ) フエニル] ェチル] ピリミジン一 4—ィルアミンと ピレスロイド化合物との重量比が 3 0 : 1〜1 : 50である請求項 1に記載の農業害 虫を防除する方法。 3. ピレスロイド化合物が、 2 - (4ーェトキシフエニル) 一 2—メチノレプロピ ノレ 3一フエノキシベンジノレ エーテル、 (RS) - α -シァノー 3—フエノキシべ ンジル (R S) - 2- (4一クロ口フエニル) 一 3—メチルブチレ一ト、 (S) 一 一シァノー 3—フエノキシベンジノレ (S) 一 2— (4一クロ口フエニル) 一 3— メチルブチレート、 (R S) 一 α—シァノー 3—フエノキシベンジル 2, 2, 3, 3—テトラメチルシクロプロパンカルボキシレート、 3—フエノキシベンジル (1 R S, 3 S ; 1 R S, 3 SR) 一 3— (2, 2—ジクロ口ビニル) 一 2, 2—ジメ チルシク口プロバンカルボキシレート、 (R S) 一 α—シァノー 3—フエノキシベン ジル (Ζ) — (1 R S, 3RS) 一 3— (2—クロロー 3, 3, 3—トリフロォ口 プロぺニノレ) 一 2, 2—ジメチルシクロプロパンカルボキシレート、 2—メチルビフ ェニルー 3—ィルメチル (Ζ) - (1 R S, 3 R S) 一 3— (2—クロロー 3, 3 , 3—トリフルォロプロプ一 1一ェニル) 一 2, 2—ジメチルシク口プロパン力ルポ キシレート、 (RS) — α—シァノー 3—フエノキシベンジル (1RS, 3 S ; 1 S, 3 SR) - 3 - (2, 2—ジクロロビニル) -2, 5-Chloro-6- (1-fluoroethyl) -N- [2- (4-1 (trifnorolomethoxy) phenyl] ethyl] pyrimidine-14 pyrimidine and pyrethroid compound represented by the following formula: A method for controlling agricultural pests that inflict the plant by applying the soil to the cultivated soil. 2. The weight ratio of 5-chloro-6- (1-fluoroethyl) -1-N- [2- [4-1 (trifluoromethyl) phenyl] ethyl] pyrimidine-1-4-ylamine and pyrethroid compound represented by the formula (A) is as follows: The method for controlling agricultural pests according to claim 1, wherein the ratio is 30: 1 to 1:50. 3. The pyrethroid compound is 2- (4-ethoxyphenyl) 1-2-methynolepropynole 31-phenoxybenzinole ether, (RS) -α-Cyanol 3-phenoxybenzyl (RS) -2- (4-1-1 3-methylbutyrate, (S) 11-cyano 3-phenyloxybenzinole (S) 12- (4-chlorophenyl) 13-methylbutyrate, (RS) 1 α- Cyano 3-phenoxybenzyl 2,2,3,3-tetramethylcyclopropanecarboxylate, 3-phenoxybenzyl (1 RS, 3 S; 1 RS, 3 SR) 1-3 (2,2-dichloro) (Vinyl) 1, 2,2-dimethylcyclopropane carboxylate, (RS) 1 α-cyano 3-phenoxybenzil (Ζ) — (1 RS, 3RS) 13-(2-Chloro-3,3,3-trifluoro) Mouth Propaninole) 1,2-dimethylcyclopropanecarboxylate, 2-methyl Off Eniru 3- Irumechiru (Ζ) - (1 RS, 3 RS) one 3- (2-chloro 3, 3 , 3-Trifluoroprop-1-enyl) 1,2,2-dimethylcyclopropane propyloxylate, (RS) — α-cyano 3-phenoxybenzyl (1RS, 3S; 1S, 3SR)- 3-(2,2-dichlorovinyl) -2,
2—ジメチルシクロプロ パンカルボキシレート及び (S) 一 α—シァノ一 3—フエノキシベンジル (1 R, 2-Dimethylcyclopropanecarboxylate and (S) -α-cyano-3- 3-phenoxybenzyl (1 R,
3 S) —2, 2—ジメチルー 3— [2- (2, 2, 2—トリフルオロー 1—トリフル 才ロメチノレエトキシカルボ二ノレ) ビュル] シクロプロパンカルボキシレートからなる 群から選ばれる 1以上の化合物である請求項 1または 2に記載の農業害虫を防除す る方法。 3 S) —2,2-dimethyl-3- [2- (2,2,2-trifluoro-1-trifluoromethylmethinoleethoxycarbinole) butyl] at least one selected from the group consisting of cyclopropanecarboxylate 3. The method for controlling an agricultural pest according to claim 1, which is a compound.
4. ピレスロイ ド化合物が、 2— (4—エトキシフエニル) 一2—メチルプロピ ノレ 3—フエノキシベンジノレ エーテル、 ( S) 一ひ:一シァノー 3—フエノキシべ ンジル (R S) 一 2— (4—クロ口フエニル) 一 3—メチノレブチレ一ト、 (S) ― α—シァノ一3—フエノキシベンジル (S) 一 2— (4一クロ口フエ二ノレ) 一 3— メチルブチレート、 (R S) 一 α—シァノー 3—フエノキシベンジル 2, 2, 3, 3—テトラメチルシクロプロパンカルボキシレート、 3—フエノキシベンジル (1 R S, 3 R S ; 1 R S, 3 SR) — 3— (2, 2—ジクロロビニル) 一2, 2—ジメ チルシクロプロパンカルボキシレート、 (RS) 一ひ一シァノ一 3—フエノキシベン ジル (Ζ) 一 (IRS, 3RS) 一 3— (2—クロロー 3, 3, 3—トリフロォ口 プロぺニル) ― 2, 2—ジメチルシク口プロパンカルボキシレート、 2—メチルビフ ェニルー 3—ィルメチル (Ζ) — (IRS, 3RS) — 3— (2—クロロー 3, 3 , 3—トリフルォロプロプー 1ーェニル) 一 2, 2—ジメチルシクロプロパンカルボ キシレート及び (R S) 一 α—シァノー 3—フエノキシベンジノレ (1 R S, 3RS ; 1RS, 3 SR) 一 3— (2, 2—ジクロロビニル) 一 2, 2—ジメチルシクロプ 口パンカルボキシレートからなる群から選ばれる 1以上の化合物である請求項 1ま たは 2に記載の農業害虫を防除する方法。 4. When the pyrethroid compound is 2- (4-ethoxyphenyl) -1-methylpropionole 3-phenoxybenzinole ether, (S) Ichihi: 1 cyano 3-phenoxybenzyl (RS) 1 2— ( 4-Sulfone phenyl) 1-3-Methynolebutyrate, (S) -α-cyano-13-phenoxybenzyl (S) 12- (4-Chlorophenyl) -13-methylbutyrate, ( (RS) 1-α-cyano 3-phenoxybenzyl 2,2,3,3-tetramethylcyclopropanecarboxylate, 3-phenoxybenzyl (1 RS, 3 RS; 1 RS, 3 SR) — 3— ( 2,2-Dichlorovinyl) 1,2,2-dimethylcyclopropanecarboxylate, (RS) 1-cyano-1-3-phenoxybenzyl (Ζ) 1 (IRS, 3RS) 1 3— (2-chloro-3,3 2,3-dimethylpropane carboxylate, 2, 3-trifluoropropionyl), 2 Methylbiphenyl-3-ylmethyl (Ζ) — (IRS, 3RS) — 3 -— (2-chloro-3,3,3-trifluoroprop-1-enyl) -1,2,2-dimethylcyclopropanecarboxylate and (RS) α —Cyanol 3-phenoxybenzinole (1 RS, 3RS; 1RS, 3 SR) 1-3 — (2,2-dichlorovinyl) 1,2,2-dimethylcyclopropane selected from the group consisting of pan carboxylate 1 3. The method for controlling agricultural pests according to claim 1 or 2, which is the above compound.
5. 農業害虫が、 半翅目害虫、 鱗翅目害虫、 鞘翅目害虫、 ァザミゥマ目害虫又は 線虫類である請求項 1〜 4のいずれかに記載の農業害虫を防除する方法。 5. The method for controlling agricultural pests according to any one of claims 1 to 4, wherein the agricultural pests are Hemiptera pests, Lepidoptera pests, Coleoptera pests, Azamazuma pests or nematodes.
6. 植物を加害する農業害虫の防除剤としての、 式 (A) 6. Formula (A) as an agent for controlling agricultural pests that infest plants
Figure imgf000018_0001
Figure imgf000018_0001
で示される 5—クロロー 6— (1—フルォロェチル) 一 N— [2- [4一 (トリフノレ ォロメ トキシ) フエニル] ェチル] ピリミジン一 4一イノレアミンとピレスロイ ド化合 物との使用。 Use of 5-chloro-6- (1-fluoroethyl) -N- [2- [4-1 (trifnorolomethoxy) phenyl] ethyl] pyrimidine-14-inoleamine and pyrethroid compound represented by the following formula.
Figure imgf000018_0002
Figure imgf000018_0002
で示される 5—クロロー 6— (1一フルォロェチル) 一 N— [2— [4一 (トリフル ォロメ トキシ) フエニル] ェチル] ピリミジン一 4一イノレアミンとピレスロイ ド化合 物とを有効成分として含有する農業害虫防除組成物。 5-Chloro-6- (1-fluoroethyl) -1-N- [2- (4- (trifluoromethyl) phenyl] ethyl] pyrimidine-14-indicated by an agricultural pest containing inoleamine and a pyrethroid compound as active ingredients Control composition.
PCT/JP2002/006714 2001-07-11 2002-07-03 Method for agricultural insect pest control WO2003007717A1 (en)

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WO2008090048A2 (en) 2007-01-26 2008-07-31 Basf Se 3-amino-1,2-benzisothiazole compounds for combating animal pest ii
EP1952690A2 (en) 2007-01-31 2008-08-06 Basf Se Pesticidal mixtures based on triazolopyrimidines and insecticides
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US8211828B2 (en) 2007-01-19 2012-07-03 Basf Se Fungicidal mixtures of 1-methylpyrazol-4-ylcarboxanilides and azolopyrimidinylamines
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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0665225A1 (en) * 1994-02-01 1995-08-02 Ube Industries, Ltd. 4-Phenethylamino pyrimidine derivative, process for preparing the same and agricultural and horticultural chemical for controlling noxious organisms containing the same
US5852023A (en) * 1995-03-29 1998-12-22 Hoechst Schering Agrevo Gmbh Cyclohexylamino and cycloalkoxy nitrogen heterocycles, processes for their preparation, and their use as pesticides and fungicides

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0665225A1 (en) * 1994-02-01 1995-08-02 Ube Industries, Ltd. 4-Phenethylamino pyrimidine derivative, process for preparing the same and agricultural and horticultural chemical for controlling noxious organisms containing the same
US5852023A (en) * 1995-03-29 1998-12-22 Hoechst Schering Agrevo Gmbh Cyclohexylamino and cycloalkoxy nitrogen heterocycles, processes for their preparation, and their use as pesticides and fungicides

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