TW201035059A - Ester compound and use thereof - Google Patents

Abstract

An ester compound represented by a formula (I) is provided, where A represents a group represented by any one of A1, A2 and A3. In each formula, R.sup.1 represents a methyl, propenyl or propynyl group, and R.sup.2 represents a methyl group. Alternatively, R.sup.1 and R.sup.2 bond with each other and represent a tetramethylene group.

Description

201035059 VI. Description of the Invention: TECHNICAL FIELD OF THE INVENTION The present invention relates to ester compounds and uses thereof. [Prior Art] A variety of conventional compounds have been developed to control pests and diseases (see The second series of pharmaceutical research and development, vol. 18, "Development of agrochemicals III", page 493, Hirokawa Shoten, 1993). For example, JP-A 〇 S57-158765 discloses certain cyclopropanecarboxylate derivatives. [Invention and Content] An object of the present invention is to provide a novel compound having an excellent pest control effect. The inventors of the present invention have intensively studied to find a compound of the formula (1) having an excellent pest control effect, and thus completed the present invention. The present invention provides an ester compound of the formula (1):

Wherein A represents a group represented by any one of the formulae A1, A2 and A3, 321738 3 201035059

In the formula, R1 represents a methyl group, a propenyl group or a propynyl group, and R2 represents a methyl group, or R1 and R2 are bonded to each other to represent a tetradecylene group; a pest control composition comprising the compound of the present invention as an active ingredient; And a method of controlling pests and diseases comprising the step of applying an effective amount of a compound of the invention to a pest or pest or a habitat of the pest. The compound of the present invention has an excellent pest control effect, and therefore it is suitable for use as an active ingredient of a pest control composition. [Embodiment] In the present invention, R1 represents a fluorenyl group, a propenyl group or a propynyl group. The propylene group contains a 1-propenyl group and a 1-propenyl group. The propynyl group includes a 1-propynyl group and a 2-propynyl group. The compounds of the invention have two asymmetric carbon atoms in the cyclopropane ring. In the compound, the relative configuration of the substituents at the 1-position and the 3-position of the cyclopropane ring is a trans conf iguration. Therefore, in the compound, when the absolute configuration of the 1-position of the cyclopropane ring is configured as R, the absolute configuration of the 3-position of the cyclopropane ring is configured as R, and when in the cyclopropane ring - The absolute configuration of the position is the S configuration, the absolute configuration of the 3-position of the cyclopropane ring is configured as S. The compounds of the present invention have isomers resulting from the presence of a double bond in the moiety -ch=c(cn)ch3 4 321738 201035059. The present invention comprises the above isomers of activity and mixtures thereof. Axis = Prevention The compounds of the present invention contain, for example, the following compounds. Species: (1) The σ object 'where' exists in the _CH=_ redundancy key relative configuration is Z configuration; Scythe < another compound of formula (1), where A矣+彳“sink A group of the formula (1), wherein A represents a group represented by the formula A1, and 〇 is present in the double bond of the _CH=C(CN)CH3 moiety. The relative configuration is z configuration; T is a compound of the formula (1), wherein A represents a group represented by the formula ,, and R represents a propynyl group; a compound of the formula (1), wherein Α represents the formula A1 a group in which r1 represents a propynyl group and is present in -(d) (the relative configuration of the double bond of the (8) (10) moiety is a Z configuration; a compound of the formula (1), wherein A represents a group represented by the formula A2; a compound of the formula (1), wherein A represents a group of the formula A2, and the relative configuration of the double bond of the oxime present in the -CH=C(CN)CH3 moiety is a z configuration; one formula (1) a compound wherein A represents a group represented by the formula A2, and R1 and R2 each represent a fluorenyl group; and a compound of the formula (1), wherein A represents a group represented by the formula A2, and R1 and R represent a fluorenyl group, respectively. And exist in _CH=c(CN)CH3 The relative configuration of the double bonds is a Z configuration; a compound of the formula (1), wherein A represents a group represented by the formula A2, and R and R2 are bonded to each other to represent a tetramethylene group; 1) a compound wherein A represents a group represented by the formula A2, and R1 5 321738 201035059 and R2 are bonded to each other to represent a tetra-indenyl group and a relative group of a double bond present in the -CH=C(CN)CH3 moiety. The state is a Z configuration; a compound of the formula (1), wherein A represents a group represented by the formula A3; a compound of the formula (1), wherein A represents a group represented by the formula A3 and is present in -CH The relative configuration of the double bond of the =C(CN)CH3 portion is a Z configuration; a compound of the formula (1), wherein A represents a group represented by the formula A3, R1 represents a propynyl group and R2 represents a fluorenyl group; A compound of the formula (1), wherein A represents a group of the formula A3, R1 represents a propynyl group, and R2 represents a thiol group and the relative configuration of the bismuth bond present in the -CH=C(CN)CH3 moiety Configuration for Z. The compound of the invention can be obtained by making a compound of formula (2): A-CH2

(wherein A represents the same definition as described above.) Compound of formula (3):

Or a reactive derivative of the compound of the formula (3) is reacted to obtain. The reactive derivative comprises an acid dentate of the compound of formula (3), an acid anhydride of the compound, or a decyl ester of the compound. The acid i compound comprises an acid chloride compound and an acid bromide compound. The reaction is usually carried out in a solvent in the presence of a condensing agent or a base. 6 321738 201035059 The condensing agent or the test system is appropriately selected depending on the kind of the compound of the formula (3) or a reactive derivative thereof. Examples of the solvent include hydrocarbons such as benzene, toluene or hexane, ethers such as diethyl ether or tetrahydrofuran, halogenated hydrocarbons such as gas, two gas, or 1,2-'dichloroethane, chlorobenzene and mixture. Examples of the condensing agent include dicyclohexylcarbodiimide and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride. Examples of the base include an organic base such as triethylamine, pyridine, N, N-diethyl f% aniline, 4-dimethylaminopyridine, or diisopropylethylamine. The reaction time is usually in the range of 5 minutes to 72 hours. The reaction temperature is usually in the range of from -20 to 100 ° C, and preferably in the range of from -5 ° C to 100 ° C. Here, when the boiling point of the solvent used is less than 100 ° C, the reaction temperature is in the range of from -20 ° C to the boiling point of the solvent, preferably from -5 ° C to the boiling point of the solvent. Q In the reaction, the molar ratio of the compound of the formula (2) to the compound of the formula (3) or a reactive derivative thereof may be appropriately selected, however, it is preferably an equimolar ratio or a close molar ratio. The condensing agent or base can be used in any ratio of from 0.25 moles to excess, preferably from 0.5 moles to 2 moles, per mole of the compound of formula (2). After the completion of the reaction, 5 the reaction mixture is filtered and concentrated, or the reaction mixture is poured into water, followed by a conventional post-treatment operation such as extraction with an organic solvent or concentration to obtain a compound of the present invention. The resulting compound of the invention of 7 321 738 201035059 can be purified by, for example, chromatography or steaming. The compound of the formula (2) is disclosed in JP-A No. H5-255271, JP-A S57-158765, U.S. Patent No. 3,345, 379, which is a commercially available product, and can be obtained by the method described in the publication. Manufacturing. Equation (3) 5 The system is exposed in Agricuiturai & Bi〇i〇gicai

ChemiStlT' 34' 1 119 (1970), and can be made by the methods described in such publications. The compound of the present invention comprises pests and diseases which exhibit an effective force, for example, a terrarium animal such as an insect or a mite. Specific examples thereof are as follows. Lepidoptera: Pyralidae such as chilo suppressalis, rice leaf roller, cnaphai〇crocis (1丨11&1丨5), and Indian rice powder moth (卩1〇(^3丨11力6印1111(^6118); Noctuidae such as gpodoptera Htura, Pseudaletia separate and Mamestra brassicae 'Teddy Pieridae such as Pierisrapae crucivora; Tortricidae such as Adoxophyes spp.; carposinidae; Lyonetiidae; Lymantriidae; night Moth (Autographa), and Agrotis spp. such as Agrotis segetum and Agrotis ipsilon; Helicoverpa spp.; Heliothis spp.; Plutella xylostella; Phyllostachys pubescens (parnara 8 321738 201035059 guttata) 'Tinea translucens; and Tine〇la bissel1iella; Diptera: Culex SPP· ) such as Culex pipiens (8116115) and _ Mosquitoes ((1, 1116} (_^丨"|:&6]11〇1*11711.11115); Aedes spp.), such as Aedes aegypti and Aedes Albopictus); An〇pheles spp. such as Anopheles sinensis; Chironomidae; Muscidae such as ordinary house rope (Musca is 丨(2)), 廄Muscina stabulans and Fannia canicularis; Calliphoridae; Sarcophagidae; Anthomyiidae such as Delia platura and Delia antique 'Tephritidae; Liriomyza sativae; Agromyzidae; Drosophilidae; pSyCh〇didae; Phoridae; (Tabanidae); Simuliidae; Stomoxyidae; and Ceratopogonidae; Blattaria: Blattella germanica, Periplaneta iuliginosa, American cockroach蠊 (Periplaneta americana), brown 蜚蠊 (Periplaneta brunnea), Oriental 蜚蠊 (Blatta orie Ntalis), et al; Hymenoptera: Formicidae, Vespidae, genus, genus 9 321738 201035059 (Bethylidae), Tenthredinidae, such as Athalia rosae Ruficornis); Siphonaptera: Ctenocephalides canis, Ctenocephalides felis, Pulex irritans; Anoplura: Pediculus humanus, Pthirus pubis ^^(Pediculus capitis) ' ^^(Pediculus corporis), et al; Isoptera: Reticulitermes speratus, Coptotermes formosanus, etc. Hemiptera: De 1 phac i dae such as Laode 1 phax striatellus, Nilaparvata lugens, and Sogatella furcifera; Deltocephalidae such as black-tailed spider mites (Nephotettix virescens) and Nephotettix cincticeps; Aphididae; Pentatomidae; Aleyrodidae; Coccidae; Cimicidae Temperate bed bug (Cimex lectularius); Tingidae; Psyllidae ', etc.; Coleoptera: Attagenus unicolor japonicus; Jiyuanjing 10 321738 201035059 worm (Authrenus verbasci ); corn rootworms such as Diabrotica virgifera & Diabrotica undecimpunctata howardi; Scarabaeidae such as Anomala cuprea and 榛吉金* Turtle (Anomala ruiocuprea); Curculionidae such as Sitophilus zeamais, Lisorhoptrus oryzophilus, Anthonomus grandis grandis and Callosobruchus chinensis; Eneenebrionidae such as Tenebrio mol itor and Tribolium castaneum; Chrysomelidae such as Oulema oryzae, Phyllotreta striolata Aulacophora femoralis; Anobi idae; Epi lachna spp. (Epilachna vigintioctopunctata); Lyctidae; Bostrychidae; Cerambycidae; and Paederus fuscipes, etc.; Thysanoptera: Southern scutellaria Horse (Thrips palmi), Frankliniella occidentalis, Thrips hawaiiensis, etc.; Orthoptera: Gryllotalpidae; Acrididae, et al; Acarina): Pyroglyphidae such as American dust mites 321738 11 201035059 (Dermatophagoides farinae) and European dust mites (Dermatophagoides pteronyssinus); Acaridae such as Tyrophagus putrescentiae and Aleuroglyphusovatus Glycyphagidae, such as Glycyphagus privates, Glycyphagus domesticus, and Glycyphagus destructor; Cheyletidae, such as the genus Cheyletus malaccensis and meat. (Cheyletus fortis); Tarsonemidae; Chortoglyphus spp.; Onyx (Oribatei) ); Tetranychidae such as Tetranychus urticae, Tetranychus kanzawai, pan〇nychus citri, and Panonychus ulmi; (Ixodidae) such as Haemaphysalis longiconis; Dermanyssidae such as Ornithonyssus sylviarum and Dermanyssus gallinae. The pest control composition of the present invention is usually a formulation, It can be composed of the compound of the present invention itself. Examples of formulation forms include oily solutions, emulsifiable concentrates, wettable powders, flowable formulations (eg, aqueous suspensions, or aqueous emulsions), microcapsules, powders, granules, bonds; agents, aerosols (aer〇s〇l), carbon dioxide formulation, heated evapotranspiration (such as insecticide coils, electrically heated insecticide tablets, or liquid absorbing core type of heated evapotranspiration), piezoelectric killing Insecticide formulation, heating fumigant (such as self-igniting fumigant, chemical anti-321738 201035059 type of fumigant, or porous ceramic plate fumigant), non-heated evapotranspiration (such as resin evaporative formulation, paper evapotranspiration) Formulations, non-woven evapotranspiration formulations, fabric evapotranspiration formulations, or sublimation tablets), aerosol formulations (eg, aerosols), direct-touch formulations (eg, sheet-type touch formulations, strip type) Touch the formulation, or the mesh type touch formulation), ULV formulation and bait. Depending on the type of formulation, these formulations will generally comprise from 0.001 to 98% by weight of the total amount of the compound of the invention. The form of the formulation as described above can be prepared, for example, by the following method. [1] A method comprising mixing a compound of the present invention with a solid carrier, a liquid carrier, a gas carrier, a bait or the like, and if necessary, adding an adjuvant or other adjuvanting agent, and then processing. [2] A method comprising impregnating a compound of the present invention in a substrate. [3] The method comprises mixing a compound of the present invention with a substrate, and then molding the resulting mixture into a shape.固体Used for the solid carrier of the formulation to give η, 只 刎 刎 包含 包含 包含 包含 包含 包含 包含 包含 包含 包含 包含 包含 包含 包含 包含 包含 包含 包含 包含 包含 包含 包含 包含 包含 包含 包含 包含 包含 包含 包含 包含 包含 包含 包含 包含 包含 包含 包含 包含 包含 包含 包含 包含 包含 包含 包含 包含 包含 包含 包含) or acid clay), synthesizing other inorganic minerals (such as sericite, sulphur dioxide, or hydrated oxidized oxide) and chemical fertilizer activated carbon, carbonic acid, ammonium chloride, or urea); Such as ammonium sulfate, 醆 〜 ~ ammonium typhate, keto-1,3,5-trioxane, naphthalene / 对 pair:, = substance (such as 2,4,6-triisopropyl (adamantine)); and blue 1 〇 樟 樟 、, or diamond wire (thread), foam, porous 丨 fiber, quasi-knitted fabric, sheet, paper, gauze and multifilament fiber, including one or 321738 13 201035059 Group heart _ : , fiber, pulp, synthetic resin ( · ' σσ, silk, cotton, marijuana, linear low-density poly-bine and high-density sound 6 ^ month purpose such as low-density polyethylene such as ethylene - ethylene Acetic acid I means 取 取 取 取 取 取 ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' ' '埽-propylene·^, agglomerate and acetamethylene ethene methacrylate and ethylene-acrylic acid ethyl acetamidine ''(10) acid methyl vinegar as ethylene-acrylic acid copolymer; olefinic phthalic acid copolymer resin Such as propylene homopolymer and bis-'tetradecene decene copolymer; polypropylene small polybutanol, polybutylene bismuth acrylonitrile-butadiene-styrene tree bismuth ethylene 'acrylonitrile' stupid Vinyl resin; resin; styrene elastomer such as lean styrene styrene; acrylic wax such as polymethyl methacrylate polyamide resin such as nylon 6 and nylon 66; Such as polyethylene terephthalate, p〇ly ethylene naphthalate, polybutylene terephthalate and polycyclohexylene dimethylene Terephthalate); or a porous resin such as polycarbonate, polyacetal, polypropylene (卩〇1丫3(^713111!〇1^), polyarylate (?〇17&〇丨&1:6 ), phenyl phthalic acid polyester, polyether phthalimide, polyester carbonate, polyphenylene ether resin, polyvinyl chloride, polyethylene dioxide Polyurethane, foamed polyamine phthalate, expanded polypropylene and expanded polyethylene), glass, metal and ceramics. Examples of liquid carriers include aromatic smoke or aliphatic Hydrocarbons (eg dimethyl 14 321738 201035059 benzene, toluene, alkyl naphthalene, phenyl xylylene ethane, kerosene, light oil, hexane, or cyclohexane); halogenated hydrocarbons (eg chlorobenzene, dichlorodecane, Dichloroethane, or trichloroethane); alcohol (such as methanol, ethanol, isopropanol, butanol, benzyl alcohol, or ethylene glycol); ether (such as diethyl ether, ethylene glycol dimethyl ether, Diethylene glycol monomethyl test, diethylene glycol monoethyl test, propylene glycol monomethyl ether, tetrahydroanion, or dioxane); ester (such as ethyl acetate or butyl acetate); ketone (such as acetone) , mercapto ethyl ketone, methyl isobutyl ketone, or cyclohexanone); nitrile (eg acetonitrile, or isobutyronitrile); hydrazine (eg dimethyl hydrazine); carboxamide (eg 〇N, N) - Dimercaptocarbamamine, N,N-dimercaptoacetamide, or N-methyl-pyrrole, I); Stretching base carbonate (for example, propylene carbonate); Oils (e.g. soybean oil, or cottonseed oil); vegetable essential oils (e.g. hanging orange oil, hyssop (hyssop square i 1), or lemon oil); and water. Examples of gaseous carriers include butane gas, chlorofluorocarbons, liquefied petroleum gas (LPG), dimethyl ether, and carbon dioxide. Examples of surfactants include alkyl sulfates, alkyl sulfonates, alkyl Q aryl sulfonates, alkyl aryl ethers, polyoxyethylated alkyl aryl ethers, polyethylene glycol ethers, polyols S is intended to be a sugar alcohol derivative. Examples of other adjuvants for the formulation include binders, dispersants, and stabilizers. Specifically, for example, casein, gelatin, polysaccharides (such as starch, gum arabic, cellulose derivatives, or alginic acid), lignin derivatives, bentonite, sugars, synthetic water-soluble polymers (such as polyethylene) Alcohol, or polyvinylpyrrolidone), polyacrylic acid, BHT (2,6-di-t-butyl-4-methylphenol), and BHA (2-tert-butyl-4-methoxyphenol) a mixture of tert-butyl-4-methoxyphenol). 15 321738 201035059 Examples of substrates for insecticide coils include plant powders (such as wood flour and les powder) and binders (such as scented granules and gluten). mixture. Examples of the substrate for the electrically heated insecticidal sheet include a sheet obtained by hardening cotton wool and a sheet obtained by hardening fibers of a mixture of cotton linters and pulp. Examples of substrates for self-igniting fumigants include combustion heat generating agents such as nitrates, nitrites, strontium salts, potassium chlorate, nitrocellulose, ethyl cellulose, and wood flour; thermal decomposition stimulators, such as a metal salt, a soil metal salt, a dichromate and a chromate; an oxygen carrier such as potassium nitrate; a combustion aid such as melamine and wheat flour; an extender such as diatomaceous earth; A binder, such as a synthetic paste. Examples of the substrate for the chemical reaction type scenting agent include a heat generating agent such as a metal sulfide, a polysulfide, a hydrogen sulfide, and an oxidizing mother; a catalyst such as a carbonaceous material, iron carbide, and activated clay; an organic foaming agent; Such as azo dimethyl hydrazine, benzene sulfonium, dinitro pentamethylenetetramine, polystyrene and polyurethane; and fillers, such as natural fiber strips and synthetic fiber strips. Examples of the substrate for the resin evapotranspiration formulation include polyethylene resins such as low density polyethylene, linear low density polyethylene, and high density polyethylene; ethylene-vinyl ester copolymers such as ethylene-vinyl acetate copolymer; Ethylene-methacrylate copolymers, such as ethylene-methyl methacrylate copolymers and ethylene-mercapto acrylate copolymers; ethylene-acrylate copolymers, such as ethylene-methyl acrylate copolymers and ethylene-acrylic acid Ester copolymer; B 16 321738 201035059 olefin-alkenyl carboxylic acid copolymer, such as ethylene-acrylic acid copolymer; ethylene tetracyclododecene copolymer; polypropylene resin, such as propylene copolymer and propylene-ethylene copolymer; Polymethylpentene-1, polybutene-1, polybutadiene, polystyrene acrylonitrile-stupid vinyl resin; acrylonitrile_丁二场-笨乙乙烤树月曰 This B-baked elastomer, such as benzene Ethylene-co-light dilute segment copolymer and gasified styrene-conjugated diene block copolymer; fluororesin; acrylic resin, such as polymethyl propyl acetate; polyamine resin, such as nylon 6 and nylon 〇66; Polyacetal resin, such as polyethylene terephthalate, polyethylene terephthalate, polybutylene terephthalate and polycyclohexylene dimethylene terephthalate. Polyacetal, polypropylene sulfone, polyarylate (p〇lyaryla1:e), hydroxybenzoic acid polyester, polyether phthalimide, polyester carbonate, polyphenylene ether resin, poly Chloroethylene, polyvinylidene chloride and polyaminoformic acid. These base materials resins may be used singly or in combination of two or more. To the right, a plasticizer such as phthalic acid ester (e.g., phthalic acid G-methyl sulphate, or dioctyl phthalate, etc.), adipate, and stearic acid may be added to these substrates. The resin evaporating formulation can be prepared by mixing the compound of the present invention with a substrate, kneading the mixture, and then molding by injection molding, extrusion molding or compression molding. If desired, the resulting resin evaporative formulation can be further subjected to a molding or cutting procedure to form a flat sheet, film, ribbon, web or thread. These resin formulations can be processed into animal collars, animal earring labels, flat products, catching ropes, gardening piles and other products.

32173S 17 201035059 Examples of substrates for baits include food ingredients such as lotus root starch, vegetable oil, sugar, crystalline cellulose; antioxidants such as dibutylhydroxytoluene and nordihydroguaiaretic acid; Agents such as dehydroacetic acid; anti-child and pet ingestants, such as red paprika; and attracting pests and diseases such as milk-flavored spices, onion flavors and peanut oil. The pest control method of the present invention comprises the step of applying an effective amount of the compound of the present invention to a pest or a habitat of the pest. In the control method, the compound of the present invention is usually applied to a pest or a pest or a pest in the form of a pest control composition. For example, the application of the compound of the present invention can be carried out according to the method below, and the specific application method can be appropriately selected depending on the form of the compound of the present invention, the place where it is to be used, and the like. (1) A method comprising treating a pest or a habitat of the pest with the compound of the present invention or the pest controlling composition of the present invention. (2) A method comprising diluting the compound of the present invention or the pest controlling composition of the present invention with a solvent such as water, and then spraying it onto a pest or a pest orbit. In the method (2), the compound of the present invention or the pest control composition of the present invention is generally diluted so that the concentration of the compound of the present invention is from 0.1 to 1000 ppm, and then sprayed. (3) A method comprising heating a pest control composition of the present invention in a habitat of a pest to evaporate a compound of the present invention. In the method (3), the application amount and the application concentration of the compound of the present invention can be appropriately selected depending on the form of the compound of the present invention, the administration time, the place of application, the method of application 18 321738 201035059, the type of pests and diseases, the damage, and the like. When the compound of the present invention is used for the prevention of epidemics, the application amount in the space where the application is carried out is usually 0.0001 to 1000 mg/m3, and the application amount is 0. 0001 to 1000 mg when the site is flat. /m2. * A heating fumigant such as an insecticide strip or an electrically heated insecticide tablet can be carried out by heating to volatilize the active ingredient according to the formulation. The application of a non-heated evapotranspiration formulation such as a resin evapotranspiration formulation, a paper evapotranspiration formulation, a nonwoven fiber evapotranspiration formulation, a woven evapotranspiration formulation or a sublimation tablet may, by way of example, be placed by itself The formulation is placed in the space to be applied, or under the action of blowing air. In the case where the compound of the present invention is used for the purpose of preventing epidemics, examples of the habitat of the pest include a closet, a Japanese kitchen cabinet, a crate, a cupboard, a toilet, a bathroom, a shelter, a living room, and a dining room. , garage and car interior. The compounds of the invention may also be applied to outdoor open spaces. When the compound of the present invention is used for controlling parasites other than livestock (such as cattle, horses, pigs, sheep, goats or chickens) or small animals (such as dogs, cats, rats or mice), it can be used in the veterinary field. Known methods of applying the compounds of the invention to animals. As for the specific method of use, when it is intended to be used for systemic control, it is administered, for example, as a tablet, a feed mixture, a suppository, and an injection (via muscle, subcutaneous, intravenous, abdominal cavity). When intended for non-systemic control, the method of administering a compound of the invention to an animal, such as spraying with a grease or aqueous liquid, pouring or spot-on treatment, washing with a shampoo formulation Animals, the resin evapotranspiration is made into a collar or earring label to be fixed on the animal 19 321738 201035059 1 kg. When administered to an animal, the amount of the compound of the present invention is usually in the range of from 0.01 to 1000 mg per body weight. The compound of the present invention can be mixed with the following agents or used together with the following agents: other killing agents & agents, smoldering agents, nematicides, soil diseases A Bao, A agents, fungicides, herbicides, plant growth Conditioner, repellent, synergist, fertilizer or soil modifier. The above-mentioned insecticide, acaricide, nematicide, soil pest control agent, fungicide, herbicide, plant growth regulator, insect repellent, synergist, fertilizer and soil modifier No special restrictions. Examples of such insecticides and smoldering active ingredients include organic can compounds such as fenitrothion, fenthi〇n, diazinon, chlorpyrifos, and dinosaur ( Acephate), methidathion, disulfoton, DDVP, sulprofos, cyanophos, dioxabenzofos, dimethoate, 赛达松Phethoate), marathion, trichlorphon, azinphosmethyl, monocrotophos or ethion; urethane compounds such as BPMC, defec Benfuracarb), propoxur, carbosulfan, carbaryl, methomyl, ethiofencarb, aldicarb, temple killing ( Oxamyl) or fenothi〇carb; 20 321738 201035059 Pyrethroid compounds, such as etofenprox, fenvalerate, esfenvalerate , fenpropathin, 赛, (cypermethrin), permethrin, cyhalothrin, deltamethrin, cycloprothrin, fluvalinate, bifenyi Bifenthrin), 2-methyl-2-(4-bromodifluorodecyloxyphenyl)propyl (3_^phenoxy alkalyl) ether, tralomethrin, Shi Xiyan vine | (silafluofen ), benzoquinone, d-phenothrin, cyphenothrin, d-resmethrin, acrinathrin, cyfluthrin, tefluthrin , transfluthrin, tetramethrin, allethrin, d-furamethrin, prallethrin, alkyne. Imiprothrin, empenthrin, 2, 2, 3, 3-tetramethylcyclopropanecarboxylate 5-(2-propynyl)furanmethyl ester, methotrex (metof luthrin) ), prof luthrin and dimefluthrin; nitroimidazole derivatives, nitroguanidine derivatives such as clothianidin and dinotefuran, N- Cyanoguanidine derivatives such as acetamiprid, chlorinated hydrocarbon compounds such as endosulfan, r-BHC and: [-bis(gas phenyl)-2,2,2-trisole ethanol, benzene Formyl phenyl gland compounds such as chlorfluazuron, teflubenzuron, and flufensulfon 21 321738 201035059 (flufenoxuron), phenylpyrazole compounds, and methoxadiazon, new kills Bromopropylate, tetradifon, chinomethionat, pyridaben, fenpyroximate, diafenthiuron, tebufenpyrad, liuyangmycin Polynactin complex (tetranactin, dinactin, trisin (trina) Examples of active ingredients of ctin)), pyrimidifen, milbemectin, abamectin, ivermectin, and azadirachtin ° insect repellents include 3 , 4-Phasediol (3,4-caranediol), N, N-diethyl-m-nonylbenzamide, 2_(2-hydroxyethyl)-1-bred bite taurine 1-mercaptopropyl Base vinegar, p-menthol-3, 8-diol and plant essential oils such as hyssop oil. Examples of the active ingredient of the synergist include bis-(2,3,3,3-tetrachloropropyl)ether (S-421), N-(2-ethylhexyl)bicyclo[2.2.1]g -5-ene-2,3-diimine (MGK-264), and α-[2-(2-butoxyethoxy)ethoxy]-4, 5-methylenedioxy 2-propyl fluorene benzene (piperonyl butoxide). EXAMPLES The present invention will be further illustrated by the following Preparation Examples, Formulation Examples and Test Examples, but the present invention is not limited to the examples. First, a production example of the compound of the present invention is shown. Production Example 1 281 g (1.47 mmol) of 1-ethyl-3-(3-didecylaminopropyl 22 321738 201035059 base) carbodiimide hydrochloride and 10 mg of 4-dimethylamino group Pyridine was added to 1 mL of 247 mg (1.47 mmol) of 3-hydroxymethyl, -(propynyl)imidazolidine-2,4-dione and 220 mg (1.23 „1111〇1) (11〇_) Trans-_"3_((Z)-2-cyano-1-propanyl)-2,2-dimercaptocyclopropanecarboxylic acid in chloroform solution. The resulting mixture was stirred at room temperature for 48 hours. Pour into the reaction mixture, and then the reaction mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and then dried under reduced pressure, and the residue obtained was subjected to a second column chromatography to obtain 134 mg. A compound of the formula (hereinafter referred to as the compound (1) of the present invention).

Yellow liquid, h-NMRiCDClhTMS) δ (ppm): 1.19(S,3H>, 1.33(s,3H), 1.69(d,lH,J = 5.3 Hz), l.95(d,3H,J = 1.4 Hz ), 2.37 (t, 1H, J = 2.5 Hz), 2.44 (dd, 1H, J = 9.5, 5.3 Hz), Q 4.05 (s, 2H), 4.27 (d, 2H, J = 2.5 Hz), 5.51 ( d, lH, J = 10.4 Hz) f 5.59 (d, 1H, J = 10.4 Hz), 5.77 (dd, 1H, J = 9.5, 1.4 Hz) Production Example 2 The same operation as in Production Example 1 was carried out, but used 1-hydroxymethyl_3,4-dimethylene-11 each-2,5-dione substituted 3-mercapto-1-(2-propyl) miso bite-2,4-dione A compound of the following formula (hereinafter referred to as the compound (2) of the present invention). 321738 23 201035059 Ο

1.18(s,3H>r1.32(s,3H), = 5.3 Η幻,Ι 95(εΐ,3υ = 1-6 Hz), 2.02(s;6H), 2.43(dd,lH,J = 9.7, 5.3 Hz), 5.50 (d, lH, J = 10.6 Rz) r 5.56 (dflHfj = i〇.6 Hz), 5.75 (ddflHf J s 9.8, 1.6 Hz) r ' Manufacturing Example 3 The same as in Manufacturing Example 1 Operation, but using 2-hydroxymethyl-5-methyl-4-(2-propynyl)_2,4-dihydro-[1,2,4]triazol-3-indole instead of 3-hydroxyindole 1-(2-propynyl)imidazolidine-2,4-dione, a compound of the following formula (hereinafter referred to as the compound (3) of the present invention) is obtained.

1.72 (d,lH/J = 5.1 Hz), 1.95 (d, 3H, J = 1.5 Hz), 2.36 (brs, 4H), 2.45 (dd, 1H, J = 9.8, 5.1 Hz), 4.44 (d, 2H) , J - 2.4 Hz) / 5.70 (4; ^^ e 11.0 Hz), 5.76 (dd, lH, J = 9.8, 1.5 Hz), 5-78 (d; 1H, j = il. O Hz) Manufacturing Example 4 The same operation as in Production Example 1 was carried out except that 2-hydroxy-3-, 5-, 6, 7-tetrahydroisoindole-1,3-dione was used to replace 3-hydroxydecyl-1-(2- Propyne 24 321738 201035059 base imidazolium-2, 4-dione, a compound of the following formula (hereinafter referred to as the compound (4) of the present invention) is obtained.

〇

Colorless crystals, lH-NMR (CDCl3, TMS) 5 (ppm): 1.18 (s, 3H), 1.32 (s, 3H), 1.66 (d, lH, J =, 5.3 Hz), 1.75-1.80 (4H, m), 1.95 (d, 3H, J = 1.4 Hz), 2.34-2.40 (m, 4H), 2.43 (dd, 1H, J = 9.7, 5.3 Hz), 5.50 (d, lH, J = 10.6 Hz), 5.56 (d, lH, J = 10.6 Hz), 5.75 (dd, lH, J = 9.7, 1.4 Hz) The matching example is shown below. All parts are by weight. Formulation Example 1 20 parts of any one of the present compounds (1) to (4) are dissolved in 65 parts of xylene, and 15 parts of Sorpol 3005X (registered trademark of Toho Chemical Co., LTD.) is added thereto. And stirring to thoroughly mix the mixture to obtain an emulsifiable concentrate. Formulation Example 2 5 parts of Sorpol 3005X was added to 40 parts of any of the present compounds (1) to (4), and the mixture was thoroughly mixed, and 32 parts of Carplex #80 (synthetic hydrous oxide oxide, Sionagi) was added thereto. A registered trademark of Pharmaceutical Co., Ltd.) and 23 parts of 300 mesh diatomaceous earth, and the mixture was stirred with a juice mixer to be mixed to obtain a wettable powder. Formulation Example 3 1.5 parts of the compound of the present invention (丨) to (4), 1 part of 25 321738 201035059

Tokuseal GUN (synthetic hydrous oxide oxide, manufactured by Tokuyama Corp.), 2 parts of Reax 85A (made of West vaco Chemica 1 s) 30 parts of Bentoni te Fu ji (bentonite, A mixture of 5 parts of Shokozan A Clay (kaolin, manufactured by Shokozan Kogyosho) was thoroughly ground and water was added thereto. The 5% granules were then obtained by granulating in a granulator and drying. Formulation Example 4 10 parts of any one of the present compounds (1) to (4), 10 parts of phenyldimethylphenylethane and 0.5 part of Sumijul L-75 (toluene diisocyanate, Sumitomo Bayer Urethane Ltd. Made) mixed. The resulting mixture was added to 20 parts of a 10% aqueous solution of gum arabic, followed by stirring with a homogenizer to obtain an emulsion having an average particle diameter of 20 μm. The emulsion was further mixed with 2 parts of ethylene glycol, and the mixture was stirred in a hot bath at 60 ° C for 24 hours to obtain a microcapsule slurry. Separately, 0.2 parts of xanthan gum and 1.0 part of Veegum R (manufactured by Sanyo Chemical Co., Ltd.) were dispersed in 56.3 parts of ion-exchanged water to obtain thickening. Solution solution. A microcapsule formulation was obtained by mixing 42.5 parts of the microcapsule slurry and 57.5 parts of the thickener solution. Formulation Example 5 A mixture of 10 parts of any one of the present compounds (1) to (4) and 10 parts of phenyldiphenylene phenylethane was added to 20 parts of a 10% aqueous solution of polyethylene glycol, followed by homogenization. The machine was stirred to obtain an emulsion having an average particle diameter of 3 μm. Separately, 0.2 part of xanthan gum and 1.0 part of Veegum R (Shi Xi 26 321738 201035059 magnesium aluminum oxide, manufactured by Sanyo Chemical Co., Ltd.) were dispersed in 58 8 parts of ion-exchanged water to obtain thickening. The solution was mixed with 4 parts of the above emulsion and 6 parts of the thickener solution to obtain a flowable formulation. Formulation Example 6 5 parts of the present compound (1) to (4), 3 parts of Carplex #8G (synthetic hydrous oxide fine powder, S10nogi 0 dirty can (6) 1 C〇·, (9) • registered trademark), 〇. 3 A portion of PAP (a mixture of phosphonium isopropyl hydrazine and diisopropyl vinegar) and 91 parts of talc (300 mesh) were obtained as a powdered juice cake. Formulation Example 7 One part of the compound (1) to (4) of the present invention was dissolved in 10 parts of dichloromethane, and the solution was mixed with 89. 9 parts of deodorized kerosene to obtain an oily solution. Formulation Example 8 One part of the present compounds (1) to (4), 5 parts of dioxane and 34 parts of deodorized kerosene are mixed and dissolved, and the resulting solution is filled into an aerosol container. The container was fitted with a valve, and 6 parts of propellant (liquefied petroleum gas) was fed into the container through the valve under M force to obtain an oily aerosol. Formulation Example 9 6 parts of the present compounds (1) to (4), 5 parts of xylene, 3.4 parts of deodorant oil and 1 part of Atmos 30 ◦ (emulsifier, Atlas Chenucal lnc. The registered trademark) is mixed and dissolved, and the obtained / combined liquid and 50 wound water are filled into the aerosol container, and the container is loaded, 321738 27 201035059 and 60 parts of the propellant are passed through the valve under pressure. (Liquified petroleum gas) is fed to the container to obtain an aqueous aerosol. The solution of the insecticide coil is used to disperse the solution and the solution of the insecticide coil. a substrate (a mixture of aromatherapy material powder, distiller's grains powder and wood powder in a ratio of 4:3:3), 100 ml of water is added thereto, the mixture is thoroughly kneaded, and the mixture is molded and dried to obtain Insecticide coils. _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ 5 cm and 0.3 cm thick electrothermal insecticide sheet substrate (in the form of a plate, obtained by hardening a fine fiber composed of a mixture of cotton wool and pulp) uniformly impregnated with 0.5 ml of the above solution An electrothermal insecticide tablet was obtained. Formulation Example 12 Three parts of the present compounds (1) to (4) are dissolved in 97 parts of deodorized kerosene, and the resulting solution is placed in a container made of polyvinyl chloride, and the liquid is absorbed. The core is inserted into the container to obtain a component for the liquid absorbing core type heating and purifying device. The liquid absorbing core is obtained by solidifying with an inorganic powder containing a binder, followed by calcination, and the upper half thereof can be heated via a heater. The aliquot of the compound (1) to (4) is dissolved in a suitable amount of the compound (1) to (4), and the solution is immersed in 4. 0 cm x 4. 0 cm and a thickness of 1 A 2 cm porous ceramic plate to obtain a heated fumigant. Formulation Example 14 • 100 μg (#g) of any one of the present compounds (1) to (4) was dissolved in an appropriate amount of acetone, and the solution was uniformly applied at 2 cm x 2 cm and a thickness of 0. A room temperature-volatilizer was obtained by removing the acetone by air drying on a 3 mm filter paper. The test examples below show that the compound of the present invention is an effective active ingredient of the pest control composition. 1% of the mixture of 0. 1% of the mixture of the chlorinated kerosene. Oily solution. Six American cockroaches (3 males and 3 females) were placed in a metal container (12.5 cm in diameter, 10 cm high), and the bottom surface of the metal container was made of a 16 〇 mesh metal mesh, and the inner surface of the metal container Thick thick cream. A container containing the American crucible was placed at the bottom of a box (46 cm x 46 cm, 70 cm thick). An oily solution (1.5 ml) was sprayed from the upper surface of the container at a pressure of 0.4 kg/cm 2 by a spray gun at a pressure of 0.4 kg/cm 2 . The container was pulled out of the chamber 30 seconds after spraying. Then calculate the number of defects that are knocked down. Other US 蟑螂 also repeat the above procedure by 2. As a control, the test was carried out in the same manner as in Test Example 1, respectively, with the following compounds, but the container was pulled out from the chamber at 29 321738 201035059 2 minutes or 15 minutes after spraying:

The compound described in Pesticide Science, 10, p. 291 (1979), and is represented by the following formula:

(referred to as comparative compound (1));

Pesticide Biochemistry and Physiology, 30, p. 251 (1988), and is represented by the following formula:

(referred to as comparative compound (2)); a compound described in JP-A S57-158765, and is represented by the following formula:

(referred to as comparative compound (3)); a compound described in W02008M02892, and is represented by the following formula: 30 321738 201035059

(referred to as comparative compound (4)); the compound described in JP-A S60-54350, and is represented by the following formula:

(referred to as comparative compound (5)); the compound described in JP-A S60-54350, and is represented by the following formula:

(referred to as comparative compound (6));

The compound described in Agricultural & Biological Chemistry, 28, p. 914 (1964), and is represented by the following formula:

〇

(referred to as comparative compound (7)). 31 321738 201035059 The fruiting system of the comparative compound of the example in which the container was pulled out of the chamber 2 minutes after the spraying was shown in Table 1. The fruiting system of the comparative compound in which the container was pulled out of the chamber 15 minutes after the spraying was shown in Table 2. Table 1 Test compound knockdown rate (%) 1 Compound of the present invention (1) 82 Compound of the present invention (2) 42 Compound of the present invention (3) 83 Comparative compound (1) 33 Comparative compound (2) 0 Comparative compound (3) 18 Comparative Compound (4) 0 Comparative Compound (5) 0 Comparative Compound (6) 0 Note 1. The compound of the present invention was measured 30 seconds after spraying. Comparative compounds were measured 2 minutes after spraying. Table 2 Test compound Knockdown rate (%) 2 Compound of the present invention (4) 42 Comparative compound (4) 0 Comparative compound (7) 8 Note 2. The compound of the present invention was measured 30 seconds after spraying. Comparative compounds were measured 15 minutes after spraying. 32 321738 201035059 [Industrial Applicability] The compound of the present invention has an excellent pest control effect, and therefore it is applied as an active ingredient of a pest control composition. » [Simplified illustration] ‘No. [Main component symbol description] Benefit.

Ο 33 321738

Claims (1)

(I) 201035059 VII. Patent application scope: 1. An ester compound of formula (1): , , , , , CH=C(CN)CH3 /\ A (the _, A represents the group represented by m, A2A A3), A1 A2 R2 N A3 is the order of 'R1? The base group, the acryl group or the bond to each other represents a tetraphenyl group and the R group is a non-methyl group, and the other is a parental control composition, and the above-mentioned compound is used as an active ingredient. A patent law 3. A method for controlling pests and diseases, including the step of applying an effective amount of the habitat of the diseased moth or the pest. The esterification mentioned in the first paragraph of the patent scope 321738 34 201035059 IV. Designated representative figure: There is no drawing in this case. (1) The representative representative of the case is: ( ). (2) A brief description of the symbol of the representative figure: 5. If there is a chemical formula in this case, please disclose the chemical formula that best shows the characteristics of the invention: 2 321738