TW200934388A - Cyclopropanecarboxylate and pest controlling composition containing the same - Google Patents

Abstract

There is provided a novel cyclopropanecarboxylate compound represented by the formula (1): wherein R1 represents a C2-C4 alkynyl group or a (C1-C4 alkoxy)methyl group, having an excellent pest controlling effect.

Description

200934388 VI. OBJECTS OF THE INVENTION · TECHNICAL FIELD OF THE INVENTION The present invention relates to a cyclopropanecarboxylate and a composition containing the same. Pest and Pest Control [Prior Art] So far, a variety of compounds have been synthesized to control pests and diseases. For example, a certain cyclopropane phthalate derivative is described in W081/02892. however

The control of pests and diseases of the cyclopropanecarboxylate derivatives described in W0 81 / 0 2 8 9 2 is not sufficient. Disclosure of the Invention An object of the present invention is to provide a novel compound having excellent pest control effects. After intensive studies, the inventors have found that the ester compound represented by the following formula (丨) has excellent pest control efficacy. Thus the present invention has been completed. That is, the present invention provides: 环 A cyclopropanecarboxylate represented by the formula (1):

Wherein R1 represents a C2-C4 alkynyl group or a (C1_C4 alkoxy)methyl group (hereinafter sometimes referred to as a compound of the invention); [2] a cyclopropanecarboxylate as shown in the above (1), wherein R1 is 2-propynyl or methoxymethyl; [3] a pest control 'composition comprising an active ingredient represented by the formula (1); and 3 320796 200934388 [4] A pest control method comprising administering an effective amount of a cyclopropanecarboxylate of the formula (1) to a pest or pest habitat. Since the compound of the present invention has excellent pest control effects, it can be used as an active ingredient of a pest control composition. [Embodiment] The best mode for carrying out the invention The compound of the invention has two asymmetric carbon atoms in the cyclopropane ring. The present invention encompasses active isomers and mixtures in all specific ratios thereof. In the present invention, examples of the C2-C4 alkynyl group include a 2-propynyl group and a 2-butynyl fluorenyl group. Examples of the (C1-C4 alkoxy)methyl group include a methoxy group and an ethoxy group. Examples of the compound of the present invention include the following compounds: A compound of the formula (1) in which the absolute configuration of the cyclopropane ring position-1 is an R-configuration; a compound of the formula (1) wherein cyclopropene The relative configuration of the substituents at position -1 and position -3 is a trans configuration; a compound of formula (1) in which the relative positions of the substituents at position -1 and position q of -3 Configured as a cis configuration; a compound of formula (1) in which the absolute configuration of the cyclopropane ring position -1 is R-configuration, and the cyclopropane ring position -1 and position -3 substituents The relative configuration is a trans configuration; a compound of the formula (1) in which the absolute configuration of the cyclopropane ring position -1 is an R-configuration and the substituents of the cyclopropane ring position -1 and position -3 The relative configuration is cis configuration; a compound of the formula (1), wherein R1 is a C2-C4 alkynyl group; 4 320796 200934388, a compound of the formula (1), wherein R1 is 2-alkyne A compound of the formula (1), wherein R1 is 2-propynyl, and the absolute configuration of the cyclopropane ring position-1 is an R-configuration; one formula (1) a compound of the formula wherein R1 is 2-propynyl, and the relative configuration of the substituents of the ring % propane ring position -1 and position -3 is a trans configuration; a compound of the formula (1) wherein R1 Is a 2-propynyl group, and the relative configuration of the substituents of the cyclopropane ring position -1 and position -3 is a cis configuration; a compound of the formula (1) wherein R1 is a 2-propynyl group, The absolute configuration of the cyclopropane® alkane ring position-1 is R-configuration, and the relative configuration of the substituents of the cyclopropane ring position-1 and position-3 is a trans configuration; one is represented by the formula (1) a compound in which R1 is 2-propynyl, the absolute configuration of the cyclopropane ring position-1 is R-configuration, and the relative configuration of the substituents of the cyclopropane ring position-1 and position-3 is cis-configuration . A compound of the formula (1), wherein R1 is (C1-C4 alkoxy)methyl; q a compound of the formula (1), wherein R1 is a methoxy group; one formula (1) is shown a compound wherein R1 is a fluorenyloxymethyl group and the absolute configuration of the cyclopropane ring position-1 is an R-configuration; a compound of the formula (1) wherein R1 is an anthracene fluorenyl group and a cyclopropane ring The relative configuration of the substituents at position-1 and position-3 is a trans configuration; a compound of formula (1) wherein R1 is an anthracene group and the cyclopropane ring is at position -1 and position -3 The relative configuration of the substituents is cis configuration; a compound of the formula (1) in which R1 is an anthracene fluorenyl group, the absolute configuration of the cyclopropane ring position -1 is an R-configuration, and the cyclopropane ring Position-1 and bit 5 320796 200934388 The relative configuration of the substituents set to -3 is a trans configuration; and, a compound of formula (1) wherein R1 is a methoxy group and the cyclopropane ring position is -1 The absolute configuration is R-configuration, and the relative configuration of the substituents for the ring propane ring position -1 and position -3 is cis configuration. 'When the compound of the invention is a mixture of isomers, examples of the mixture of isomers comprise the following mixture: a mixture of isomers comprising 50% or more of the compound of formula (1) wherein the position of the cyclopropane ring The relative configuration of the -1 absolute configuration to the R-configuration and the cyclic propane ring position -1 and position -3 substituents is a trans configuration; 〇 an isomer mixture comprising 80% or 80% The compound of the above formula (1) wherein the absolute configuration of the cyclopropane ring position-1 is R-configuration and the relative configuration of the substituents of the cyclopropane ring position-1 and position-3 is a trans configuration; A mixture of isomers comprising 90% or more of the compound of formula (1) wherein the absolute configuration of the cyclopropane ring position -1 is R-configuration and the cyclopropane ring position -1 and position -3 The relative configuration of the substituents is a trans configuration; an isomer mixture comprising 50% or more of a compound of the formula (1) above wherein R1 is 2-propynyl and the cyclopropane ring position is - The absolute configuration of 1 is R-configuration, and the relative configuration of the substituents of the cyclopropane ring position -1 and position -3 is a trans configuration; a mixture comprising 80% or more of a compound of the formula (1) wherein R1 is 2-propynyl, the absolute configuration of the cyclopropane ring position-1 is R-configuration, and the cyclopropane ring position is -1 The relative configuration of the substituents with position-3 is a trans configuration; an isomer mixture comprising 90% or 90% of the compound of formula 6 (1) 6 796 796 200934388 ^ wherein R 1 is 2-propyne The absolute configuration of the position of the cyclopropane ring -1 is R-configuration, and the relative configuration of the substituents of the cyclopropane ring position -1 and position -3 is a trans configuration; a mixture of isomers, including 50% or more than 50% of the compound of the formula (1) wherein R1 is a fluorenyloxymethyl group, the absolute configuration of the cyclopropane ring position-1 is an R-configuration, and the cyclopropane ring position is -1 and the position -3 The relative configuration of the substituents is a trans configuration; an isomer mixture comprising 80% or 80% of the compound of formula (1) wherein R1 is an anthracene group and the cyclopropane ring is at position -1. Absolutely configured as an R-configuration, and the relative configuration of the substituents of the cyclopropane ring position -1 and position -3 is a trans configuration; an isomer mixture comprising 90% or more A compound of the formula (1) wherein R1 is an anthracene fluorenyl group, the absolute configuration of the cyclopropane ring position-1 is an R-configuration, and the relative configuration of the substituents of the cyclopropane ring position-1 and the position-3 It is a trans configuration; ^ Here, the ratio of each isomer mixture means the content of the isomer in the mixture of isomers. The compound of the present invention can be produced, for example, by the following production method. Manufacturing Method 1 A method comprising the alcohol compound represented by the formula (2):

Wherein R1 represents a C2-C4 alkynyl group or a (C-C4 alkoxy) fluorenyl group which is reacted with a carboxylic acid of the formula (3): 7 320796 200934388

HO r

Cf2h This reaction is usually carried out in the presence of a condensing agent and a base. This reaction is usually carried out by spraying. Examples of the presence of the catalyst include dicyclohexyl quinone diimine and 3 (3-methylaminopropyl) carbodiimide hydrochloride. Alkali soil such as triethylamine, pyridine, N N_ 二美茉 彳匕 3 organic base - and its..., amide, 4, dimethyl aminyl amide

Examples of the acid catalyst include inorganic acids such as sulfuric acid, and hydrazines such as p-toluenesulfonic acid and methanesulfonic acid. The solvent which can be used is inert, and examples thereof include hydrocarbons such as toluene in the reaction such as diethyl- and tetrahydrogen; _ = '趟, 1,2-dichloroethane; and mixtures thereof. The reaction time of gas-fired gas is usually from instant to 72 hours, and the reaction temperature is usually from ~2〇C to 100. (: within the scope.

The amount of the alcohol compound represented by the formula (2) in the reaction is theoretically! Moer (Help 1) to 1 Moer (3) shown, ", can be appropriately selected for the 1 Moer (3) shown as the G. 5 magic. 5 Moule range. When the reaction in the condensing agent When it is carried out in the presence of a base, the amount of the condensing agent used in the reaction is usually in the form of a carboxylic acid represented by the formula (3). However, it can be appropriately changed depending on the reaction state. The amount of the carboxylic acid represented by the formula (3) is usually in the range of 〇.丨 to 1 mole. When the reaction is carried out in the presence of an acid catalyst, the amount of the acid catalyst in the reaction is 1 mole. The tannic acid represented by the formula (3) is usually in the range of from 0.01 to 20 moles, however, it may be appropriately changed depending on the reaction conditions. 8 320796 200934388 • After the reaction is completed, the reaction mixture can be conventionally The post-treatment operation is, for example, poured into water, followed by extraction with an organic solvent and further concentration to separate the compound of the present invention. If necessary, the compound of the present invention isolated in this manner can be purified by a purification operation such as chromatography and evaporation. Method 2 A method comprising the alcoholation of formula (2) The compound is reacted with a reactive derivative of a carboxylic acid represented by the formula (3) (e.g., a mercapto halide, an acid anhydride, etc.). The reaction is usually carried out in the presence of a base. The reaction is usually carried out in a solvent. Examples include organic bases such as triethylamine, pyridine, N,N-diethylaniline, 4-didecylaminopyridine and diisopropylethylamine. The solvent used may be a solvent which is inert in the reaction. Examples include hydrocarbons such as methyl and hexane; ethers such as diethyl ether and tetrahydrofuran; halogenated hydrocarbons such as chloroform, dichlorodecane and 1,2-dichloroethane; and mixtures thereof. The temperature 反应 of the reaction for an instant to 72 hours is usually in the range of -20 ° C to 10 ° C. The amount of the alcohol compound represented by the formula (2) in the reaction is 1 mol to 1 mol. 5摩尔的。 The molar derivative of the carboxylic acid of the formula (3), however, the reactive derivative of the carboxylic acid of the formula (3) is generally selected 〇. 5 to 2. 0 molar The amount used in the reaction is usually 1 mole to 1 mole of the reactive derivative of the carboxylic acid represented by formula (3), however ' It can be appropriately changed according to the reaction conditions. After the reaction is completed, the reaction mixture can be isolated from the present invention by a conventional post-treatment operation such as pouring into water, followed by extraction with an organic solvent and further thickening to reduce the compound of the present invention 9 320796 200934388. If necessary, the inventive product isolated in this manner can be purified by a purification operation such as chromatography and distillation.

The alcohol compound represented by the formula (2) may be a compound described in Jp_A 57-123146 or jp_A 61-207361, or may be produced according to the methods described in the above documents. ’

The method for producing the carboxylic acid represented by the formula (3) and the reactive derivative thereof will be described later. V Further The compound of the present invention can be produced by the production method 3 or the like. Production Method 3 ❹ f The compound of the present invention can be obtained from the compound of the formula (4):

Wherein R1 is produced by reacting with a fluorinating agent as defined above. This reaction is usually carried out in the presence of a solvent. Examples of the solvent include halogenated hydrocarbons such as monooxon and chloroform; hydrocarbons such as toluene and condensed; and mixtures thereof and the like. Examples of the fluorinating agent include diammonium trifluorosulfide and diethylaminosulfur trifluoride. The amount of the fluorinating agent used in the reaction is usually in the range of 2 equivalents to 6 equivalents per equivalent of the compound represented by the formula (4). The reaction time of the reaction is usually in the range of from 1 to 24 hours, and the reaction temperature is usually in the range of from room temperature to 100 °C. After completion of the reaction, the reaction mixture can be isolated from the present invention by a conventional post-treatment operation such as pouring into water, followed by extraction with an organic solvent and further concentration. If necessary, in this way, the compound of the present invention can be purified by a purification operation such as chromatography and evaporation. The compound represented by the formula (4) can be produced according to the method described in JP-A-2003-206264, because the compound of the present invention has two asymmetric carbons in the propylene ring. Therefore, the compounds of the present invention have four isomers, and wherein ri is the same oxime, the four isomers, ie, (10)-trans phase, (10)-trans isomer, (10)-cis isomer and (1S>_cis isomer may be produced from the respective corresponding isomers of the ruthenium (or its reactive derivative) represented by the formula (3) or the disk compound represented by the formula (4). Position f refers to the position of the cyclopropane ring here, "(1R)" and "(1S)" mean the absolute configuration. "trans" and "cis" mean the relative group of substituents at position -3 The carboxylic acid of the formula (3) can be produced by the following method.

HO

CF2H Ο (3)

MeO^ qf2h-O ◎ MeO^^A-CHO —— Ο (5) (6) A compound represented by the formula (6) can be produced from a compound represented by the formula (5): a compound represented by the formula (5) and a fluorinating agent can be used. The reaction is carried out to produce a compound represented by the formula (6). This reaction is usually carried out in the presence of a solvent. Examples of the solvent include halogenated fe such as monochloromethane and chloroform; hydrocarbons such as a stupid and condensed; and mixtures thereof and the like. Examples of the fluorinating agent include dimethylaminosulfur trifluoride and diethylaminotrifluoro 32 〇 796 11 200934388 sulphur. The fluorinating agent is usually used in the reaction in an amount of from 2 equivalents to 6 equivalents per equivalent of the compound of the formula (5). The reaction time of the reaction is usually in the range of 丨 to 24 hours, and the reaction temperature is usually in the range of room temperature to loot:. After the reaction is completed, the reaction mixture can be isolated from the compound of the formula (6) by a conventional post-treatment operation such as pouring into water, followed by extraction with an organic solvent and further concentration. The compound represented by the formula (6) which is isolated in this manner can be purified by a purification operation such as chromatography and distillation, if necessary.

The citric acid represented by the formula (3) is produced from the compound represented by the formula (6): The compound represented by the formula (8) can be hydrolyzed in the presence of the test to produce the tickic acid represented by the formula (3). This reaction can be carried out in the presence of a solvent. Examples of the solvent include alcohols such as methanol and ethanol '丄4-dioxane, water, and the like. Examples of the base include sodium hydroxide and potassium hydroxide. For the compound of the formula (6), the amount of the base may be usually 丨mol or 丨mol. The reaction time of the reaction is usually in the range of 丨 to 24 ' 呷 * J呷

The temperature is usually in the range of room temperature to 150 °C. After the core operation is, for example, addition, and the reaction is completed further, the reaction mixture can be acidified by post-treatment with an acid to be acidified, followed by extraction with an organic solvent to concentrate the citric acid represented by the formula (3). The compound of the formula (5) is produced by the method described in (b) π~j j Lett., 1981' 1097. The reactive derivative of the formula (4) (IV) can be produced by an acid method. 320796 12 200934388 'An example of a pest in which the compound of the present invention can exert efficacy includes harmful arthropods such as harmful insects and wallworms. Specific examples are as follows. Lepidoptera: , Pyralidae such as chn〇suppressalis (Darkworm), Cnaphalocrocis medinalis (rice) and Indian glutinous moth ( Plodia interpunctella), Noctuidae, such as Spodoptera litura, Pseuda 1 etia separate (rice marching insect) and cabbage (Mamestra brassicae) (cabbage march) Insects, Pieridae, such as Pieris rapae crucivora (common cabbage butterfly), Tortricidae, such as Adoxophyes spp., Carposinidae, Lyonetiidae ), Lymantriidae, Autographa, Agrotis spp., such as Agrotis segetum (Agrotis segetum) and Agrotis ipsilon (black marching insect), Helicoverpa spp., Heliothis spp., Plutella xylostella (Dragonback moth), Parnara guttata 'Tinea translucens ), Tineola bisselliell (woven nets moth) and so on. Diptera: (Culex spp.) such as Culex pipiens pal lens (ordinary mosquito) and culex tritaeniorhynchus, Aedes spp. such as Egyptian plaque Mosquito 13 320796 200934388 (Aedes aegypti) and Aedes alb〇pictus, Anopheles spp., such as An 〇pheles sinensis, Chironomidae, Muscidae ) such as Musca domestica (home rope), Muscina sfabuians and Fannia canicuiaris, Calliphordiae, sarc〇phagidae, flower rope Anthomyiidae such as ash ei ia piatura and Delia antique, Tephritidae, Agromyzidae, Drosophilidae, moths Psychodidae), phoridae, Tabanidae, Simuliidae 'stomoxyidae, Ceratopogonidae, etc. Blattaria: Blattel la germanica (German weft), Peniplaneta fuliginosa (Panplaneta fuliginosa), Periplaneta americana (American cockroach), brown cockroach p (Periplaneta brunnea) (brown 蟑螂), Oriental 蜚蠊 (Blatta orientalis) (Oriental 蟑螂) and so on. Hymenoptera: Formicidae, Vespidae, Bethylidae, Tenthredinidae, such as Athalia rosae ruficornis. Siphonaptera: Ctenocephalides canis, I nursery 14 320796 200934388 ' (Ctenocephalides felis), human 蚤 (pulex irritans) and so on. Anoplura: Pediculus humanus, Phthirus pubis, Pediculus capitis pedicuis corporis, etc. Isoptera: Yellow-legged termites (1^1: 沁111 derivatives 61*11^3 3?6 "& plus 3), Taiwanese termites CCoptotermes formosanus) and so on. ❹ Hemiptera: De 1 phac i dae such as Laode 1 phax striatellus, Nilaparvata lugens (Brown rice planthopper) and Whitebacked planthopper (Sogatella furcifera) (Dal tocephal idae), such as Nephotettix vi rescens (green rice leafhopper) and Nephotet t ix cincticeps (green rice leafhopper), Aphididae, Pentatomidae, Aleyrodidae, Coccidae 'Cimicidae', such as bed bug (Cimex lectularius) 'Tingidae', T. cerevisiae (Psyliidae) and so on. Coleoptera: Attagenus unicolor japonicus (Hymenoptera sinensis), H. sylvestris (People 111; 11^11115 ¥6:1^85€〇, corn rootworm such as corn Diabrotica virgifera (Western corn rootworm), Diabrotica undecimpunctata howardi (South 15 320796 200934388 square corn rootworm), Scarabaeidae (such as gold and copper turtle (Anoma 1 a cuprea) (Green Tortoise) and Anoma 1 a rufocuprea (soybean aphids), Curculionidae such as Sitophilus zeamais, Lisorhoptrus oryzophi lus, cotton boll symbol Anthonomus gradis grandis) and Callus edulis (Callosobruchus chinensis) (Traditional Physalis), Tenebrionidae such as Tenebrio molitor and Tribolium castaneum, gold Chrysomel idae, such as Oulema oryzae (rice mud bomb), Phyllotreta striolata and Aulacophora femoral is, Anobiidae, Epilachna spp., such as Epilachna vigintioctopunctata, Lyctidae, Bostrychidae, Cerambycidae, Paederus fuscipes ). Thysanoptera: Thrips palmi, Frankliniel la occidental is, Thrips hawaiiensis, etc. Orthoptera: Elk Gryllotalpidae), Acrididae, etc. Acarina: Pyroglyphidae such as Dermatophagoides farinae and European dust worm 200934388 * (Dermatophagoides ptrenyssnus), Acaridae such as rot Tyrophagus putrescentiae and Aleuroglyphus ovatus, Glycyphagidae such as Glycyphagus privates, Glycyphagus domesticus and Glycyphagus destructor, meat Cheyletidae such as the genus (Cheyletus inalaccensis) and the genus Cheyletus fortis, Tarsonemidae , Chortoglyphus spp., Oribatei, Tetranychidae such as Tetranychus urticae, Tetranychus kanzawai, Panonychusciti (Citrus red lacks 1 spider) and Panonychus ulmi (European red snail), I xod i dae such as long-horned blood scorpion (Haemaphysa i s longicornis), thorns Dermanyssidae) such as the northern fowl (0oiith〇nyssus sylviarum) and the red fowl (Dermanyssus ❹ gallinae). The pest control composition of the present invention contains the compound of the present invention as a living steep wound. The pest control composition of the present invention may be the compound of the present invention itself or may be formulated into the following types. Examples of the formulation type include an oil solution, an emulsifiable concentrate, a wettable powder, a flowable formulation (e.g., an aqueous suspension, an aqueous emulsion), a microcapsule, a powder (d), a granule, a lozenge. , aerosol 'carbon dioxide blending, can be heated to evaporate formulations (such as insecticide coils, electrically heated insecticides or heated evaporative pesticides with liquid absorption core), pressurized insecticides 320*796 17 200934388 Formulation, heating = agent (such as 'self-igniting agent, chemical reaction type, 'or porous ceramic board'), non-heating evaporative formula (eg, tree ^, hairy formulation, Impregnated paper evaporative formulation, evaporative formulation of woven cloth, evaporative formulation of woven fabric, or sublimable tincture), aerosol formulation (such as 1 spray formulation), direct contact with Tatsusaki (eg, #状contact formulation, strip contact formulation, or mesh contact formulation), ULV formulation and bait. When the pest control composition of the present invention is a type of the formulation, the formulation can be formulated, for example, by the following method. (1) A method comprising the step of mixing a compound of the present invention with a solid carrier, a liquid carrier, a gas carrier or a poison bait, and if necessary, a surfactant and other adjuvants may be added and further processed. (2) A method comprising infiltrating a compound of the present invention into a substrate containing no active ingredient. (3) A method comprising mixing a compound of the present invention with a substrate, followed by shaping the resulting mixture. When the pest control composition of the present invention is of the type of the formulation, depending on the type of the formulation, such formulations usually contain from 1 to 98% by weight of the compound of the present invention. Examples of solid carrier for blending include finely powdered or granular clay (such as kaolin, diatomaceous earth, bentonite, fubasamiclay, or acid white clay), synthetic aqueous cerium oxide, talc, ceramics, and other inorganic minerals. Substances (eg sericite, quartz, sulphur, activated carbon, calcium carbonate, or hydrated cerium oxide) and chemical fertilizers (such as ammonium sulphate, ammonium phosphate, ammonium nitrate, ammonium sulphate, or urea); a substance that is solid (eg, 2,4,6_ 18 320796 200934388 • triisopropyl_1,3,5_triterpene,cai,p-dichlorobenzene, off-brain, or diamond); and felt, fiber, Fabric, knitted fabric, lithographic, paper, thread, foam, porous material and multi-fiber, etc., including one or more substances selected from the group consisting of wool, silk, cotton, hemp, wood pulp, synthetic Qin Resins (for example, polyethylene resins such as low-density polyethylene baking, direct-bond low-density polyethylene and high-density polyethylene; ethylene-vinyl ester copolymers such as ethylene-vinyl acetate copolymer; ethylene-methacrylate copolymerization Object Such as ethylene-methyl methacrylate copolymer and ethylene-mercapto acrylate copolymer; ethylene- 〇 acrylate copolymer such as ethylene-methyl acrylate copolymer and ethylene-ethyl acrylate copolymer; ethylene-vinyl carboxylate Acid copolymers such as ethylene-acrylic acid copolymers; ethylene-tetracyclododecene copolymers; polypropylene resins such as propylene homopolymers and propylene-ethylene copolymers; poly-4-methylpentene-1, polybutene -1, polybutadiene, polystyrene; acrylonitrile-styrene resin; acrylonitrile-butadiene-styrene resin; styrene elastomer such as styrene-conjugated diene block copolymer and hydrogenated benzene Ethylene-conjugated diene block copolymer; fluorine-containing resin Q; acrylic resin such as polymethyl methacrylate; polyamine resin such as Nylon 6 and Nylon 66; polyester resin such as poly pair Ethylene phthalate, polyethylene naphthalate, polybutylene terephthalate and poly(trimethylene terephthalate); or porous resin such as polycarbonate, polycondensation Aldehydes, polypropylene oximes, polyarylates, hydroxybenzoic acid polyesters, polyether oximines, Ethyl carbonate, polyphenylene ether resin, polyvinyl chloride, polyvinylidene chloride, polyurethane, foamed polyaminophthalate, expanded polypropylene and foamed ethylene), glass, metal and ceramics . Examples of liquid carriers include aromatic or aliphatic hydrocarbons (e.g., xylene, A 19 320796 200934388 benzene, alkyl naphthalene, phenyl diphenyl phenyl ethane, petroleum, light oil, hexane, or cyclohexane). Alkanes, _ hydrocarbons (eg, benzene, dichloro decane, dichloroethane, or tri-ethane), alcohols (eg, sterols, ethanol, isopropanol, butanol, hexanol, Phenyl sterol, or ethylene glycol), ethers (eg, diethyl ether, ethylene glycol dimethyl ether, diethylene glycol monodecyl ether, diethylene glycol monoethyl ether, propylene glycol monomethyl ether, Tetrahydrofuran or dioxane); esters (eg, ethyl acetate or butyl acetate), ketones (eg, acetone, methyl ethyl ketone, decyl isobutyl ketone, or cyclohexanone), nitrile Classes (eg, acetonitrile, or isobutyronitrile), sulfoxides (eg, dimethyl hydrazine), guanamines (eg, N,N-didecyl decylamine, N,N-dimethyl acetamidine) An amine, or N-methyl-pyrrolidone), an alkylene carbonate (eg, propylene carbonate), a vegetable oil (eg, soybean oil, or cottonseed oil), a plant essential oil (eg, orange oil, Hessian oil, or lemon oil , As well as water. Examples of gaseous carriers include butane gas, carbon fluorinated carbon, liquefied petroleum gas (LPG), dimethyl ether, and carbon dioxide gas. Examples of the surfactant include an alkyl sulfate salt, an alkyl sulfonate, an alkyl aryl sulfonate, an alkyl aryl ether, a polyoxyethylated alkyl aryl ether, a polyethylene glycol ether, Polyol esters and sugar alcohol derivatives. Examples of other adjuvants for formulation include a binder, a dispersant, and a stabilizer. Specifically, examples thereof include cool proteins, gelatin, polysaccharides (eg, powder, gum arabic, cellulose derivatives, or alginic acid), lignin derivatives, bentonite, sugars, synthetic water-soluble polymers (eg, Polyvinyl alcohol, or polyvinylpyrrolidone), polyacrylic acid, BHT (2,6-di-t-butyl-4-methylphenol) and BHA (2-tert-butyl-4-methoxyl) a mixture of phenol and 3-tert-butyl-4-decyloxy). 20 320796 200934388 • An example of a substrate for a 35 insect insect thread comprises a vegetable powder such as wood flour fish wine powder, and a binder-domain fragrance (four) powder, a heterozygous mixture. Examples of the substrate of the electrically heated insecticidal tablet include fine fibers which are hardened into a plate-like velvet, and a mixture of the lint and pulp which is hardened into a plate shape. Examples of the substrate of the self-igniting agent include a heat generating agent such as a salt, a nitrite, a barium salt, a potassium chlorate, a nitrocellulose, an ethyl fiber and a wood powder, a thermal decomposition stimulating agent such as a metal salt, and a test. Earth metal salt, heavy acid salt and chromate, oxygen supply agent such as tartaric acid, combustion aids such as ί = with small flour, increments _ such as residual soil, and adhesion _ Ruhe = chemical reaction type Examples of the substrate include a heat generating agent such as a metal sulfide, a polysulfide, a sulfur hydride and an oxygen _, a catalyst such as a hard white clay 'organic foaming agent such as azo dimethyl =: dinitropentamethylene four Examples of substrates of amines, polystyrenes and lanthanum polycarboxylates, and fillers such as natural fiber oxime resin formulations such as resin evaporative formulations include == low density polyethylene, linear low density polyethylene Copolymer with high vinegar such as acetamidine-vinyl acetate vinegar's ethylene-mercapto acrylate copolymer copolymer with ethyl phenoxymethyl methacrylate - Acrylic vinegar poly: copolymer and ethylene - acrylic acid Twenty = things such as glacial acrylic acid copolymer; propylene; poly propylene tree riding class such as propylene copolymer and propylene ... copolymer '[" ketone 320796 21 200934388 % olefin, polystyrene, acrylonitrile-stupid vinyl; Acrylonitrile-butadiene-phenethyl olefin resin; styrene elastomer such as styrene-conjugated diene block copolymer and hydrogenated styrene-co-diene block copolymer; fluorine-containing resin; Acrylic resins such as methyl polymethacrylate; polyamine resins such as Nylon 6 and Nylon 66; polyester resins such as polyethylene terephthalate, polyethylene naphthalate 'poly Butylene terephthalate and poly(terephthalic acid) cyclohexyl dimethyl ester, polycarbonate, polyacetal, polypropylene (p〇lyacryl sulf one) 'polyaryl vinegar 'hydroxy benzoic acid polyester' Ether quinone imine, polyester carbonate, polyphenylene ether resin, polystyrene, polyvinylidene chloride and polyaminophthalate. These substrates may be used singly or in combination of two or more kinds. If necessary, these substrates may be added with a plasticizer such as a phthalate (e.g., benzo-I-f Sa benzene-m sig), adipic acid and stearic acid. The resin formulation can be prepared by mixing the present compound with a substrate, followed by injection molding, molding.

Further, extrusion molding, press molding, or the like may be carried out by further molding or by a shape such as a tape, a mesh or a wire. These resins, animal earrings, iron, flake products, such as slow powder, vegetable oil, hydroxytoluene and lowering anti-child or pet ingestion such as cheese flavor, 320796 22 200934388 onion flavor and peanut oil. The pest control method of the present invention comprises applying an effective amount of the compound to a pest or pest habitat. The method of controlling pests and diseases of the month 4 is to apply an effective amount of the compound of the present invention, usually in the form of a formulated form, to a pest or pest. The method of using the compound of the present invention is not particularly limited, and may be appropriately selected depending on the type of application, the site of application, and the like.实例 Examples of methods of use include the methods described below. (1) A method comprising the use of the compound of the present invention itself in the habitat of pests or pests. (2) A method comprising diluting a formulation of the compound of the present invention with a solvent such as water, and then spraying the diluted solution onto a pest or pest habitat. In this method, the compound of the present invention is usually formulated into an emulsifiable concentrate, a wettable powder, a flowable formulation, a microcapsule or the like. The formulation is usually diluted so that the concentration of the compound of the invention prior to spraying can reach from 1 to 10,000.

Ppm ° (3) - A method of heating or placing a compound of the present invention in a pest habitat to volatilize the compound of the present invention from the composition. For example, when the compound of the present invention is prepared into a insecticide coil or an electrically heated insecticidal tablet, the compound of the present invention can be volatilized and diffused by heating the formulation. When the compound of the present invention is prepared into a resin evaporative formulation, a dipped paper evaporative formulation, a non-woven evaporative formulation, a woven fabric evaporative formulation 23 320796 200934388 or a sublimable lozenge, the formulation is placed in a pest control space. The compound of the present invention can be volatilized and diffused in the presence or absence of air circulation. The control method of the present invention can be used for the purpose of epidemic prevention and ectoparasite control. There are no special restrictions on the habitat of pests. As long as the pests are inhabited, the habitat can be space, or planes such as the ground and land. When the compound of the present invention is used for epidemic prevention purposes, examples of pest habitat include a closet, a Japanese cabinet, a chest of drawers, a cupboard, a bathroom, a bathroom, a storeroom, a living room, a dining room, a garage, and a car interior. The compounds of the invention may also be used in open spaces outdoors. In the control method of the present invention, the application amount and application concentration of the compound of the present invention can be appropriately determined depending on the type of the control agent, the administration time, the application site, the administration method, the pest type, the damage situation, and other factors. 0001至1000。 When the use of the present invention is in the range of 0.0001 to 1000 mg / m 3 (mg / m3) of the compound of the present invention, the amount of the use of the surface is 0. 0001 to 1000 A compound of the invention in milligrams per square meter (mg/m2). When the compound of the present invention is used for controlling parasites other than livestock, such as cows, horses, pigs, sheep, goats and chickens, and small animals such as dogs, cats, rats and small mice, the pest control composition of the present invention can be learned by veterinarians. The method is applied to these animals. In particular, when systemic control is desired, the pest control composition of the present invention can be administered as a lozenge, a mixture with a feed or a suppository, or by injection (including intramuscular, subcutaneous, intravenous and intraperitoneal injection). On the other hand, when non-systemic control is desired, the disease of the present invention 24 320796 200934388 • The method for applying the pest control composition to an animal is sprinkling, washing or spotting in the form of an oil solution or an aqueous liquid, or scouring Fine-tuning the animal for washing, or wearing a slave or ear tag on the animal. The dose of the compound of the invention will generally range from 01 to 1 mg (mg) per kg (kg) of animal body weight. The compounds of the present invention may be used in admixture or in combination with one or more other insecticides, acaricides, nematode agents, soil pest control agents, mold removers, herbicides, insect repellents, and/or synergists. Examples of active ingredients of cockroach insecticides and sputum worms include: organic filler compounds such as dixel〇rvos, fenitrothion, cyanosephines, profenofos, killing Suipprofos, phenthoate, isoxathion, tetrachlorvinphos, fenthion, chlorpyrifos, diazinon, oxazolone (acephate), terbutfos (terbufos), phorate, chlorethoxyfos, fosthiazate, ethoprophos, cadusafos, dextrosone ( Methidathion), disulfoton, dioxabenzpfos, dimethoate, phenthoate, malathion, trichlorphon, azinphos-methyl , monocrotophos, ethion, etc.; urethane compounds such as propoxur, calpo 25 320796 200934388 (carbaryl), metoxadiazone, butyl extinction虱' (fenobucarb), Na Nai Methomyl, thiodicarb, alanycarb, benfuracarb, oxamyl, aldicarb, metiocarb, butyl plus Carbosulfan), ethiofencarb, fenothiocarb, cartap, etc. Pyrethroid compounds (pyre thro id) such as allethrin Tetramethrin, prallethrin, d-phenothrin, d-resmethrin, cyphenothrin, permethrin, Cypermethrin, alpha-cypermethrin, zeta-cypermethrin, deltamethrin, tralmethrin, cyfluthrin, /3 -beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, d-furamethrin, imiprothrin, Ethofenprox, fenvalerate, esfenvalerate, fenprop Athrin), silafluofen, bifenthrin, transiluthrin, flucythrinate, tau-fluvalinate, acrinathrin, tefluthrin (tefluthrin), cycloprothrin, metof luthrin, prof luthrin, dimefluthrin, and esporin , flumethrin 26 320796 200934388 * (Humethrin), flumethina (fiuvalina1; e), 2 曱 _2 2 - (4_ dimethyl difluoro oxime) propyl (3- phenoxy benzoate Base test (2-111 €1; 1171-2-(4-bromodifluoromethoxyphenyl)propyl(3-phenoxybenzyl)•ether)' and 2, 2, 3, 3-tetramethylcyclopropanecarboxylic acid 5-(2- Propynyl) ° ° Nan A Sa new compounds such as acetam: [prid], nitenpyram, thiacloprid, thiamethoxam, furosemide Amine (dinotefuran), clothianidin, imidacloprid, etc.; Ο chlorinated hydrocarbon compounds such as endosulfan, r _BHC, hydrazine, 2 pairs Phenyl phenyl)-2,2,2-trichloroethanol, etc.; basic basal gland compounds such as lufenur〇n, chlorfluazuron, hexaflumuron, bisflulon (diflubenzuron), trifiumuron, teflubenzuron, fiufenoxuron, fluauron, novalon (novaiur〇n), triazur〇n , bistrifluron, bisflufuron, fiufen〇xur0n, etc.; juvenile hormone analogues such as pyripr〇xyfen, metoprene, hydroprene, Phenoxycarb, etc.; base group compounds such as acet〇pr〇le, pyriprole, pyrafipirin, pyrithione (ethiprole), etc.; this brewing compound such as tebufenozide, chromafenozide, fenfluno, chlorantranium 27 320796 200934388 (halofenozide), etc.; macrolide compounds such as Pan J Penicillin complex (p〇1 ynact iη complex) [tetranactin, dinomycin (dinac) Tin) with trinactin, abamectin, emamectin benzoate, spinosad, ivermectin, azadirachtin, Milbemectin, etc.; and diafenthiuron, pymetrozine, flonicamide, triazamate, buprofezin' Spinosad), emamectin benzoate' chiorfenapyr, indoxacarb MP 'pyridalyl, cyromazine, fenpyroximate' Tebufenpyrad, tolefenpyrad, pyridaben, pyrimidifen 'fluacrypyrim, etoxazole, quinazaquin, aachen

Q (acequinocyl), hexythiazox 'clofentezine, fenbutatin oxide, dicofol, propargite, abamectin, avi Avermectin, milbemectin, amitraz, bensultap, thiocyclam, endosulfan, spirodiclofen, snail Snail (spiromesifen), amidoflumet and azadirachtin 'bromopropylate', decochal 28 320796 200934388 1 (tetradifon) 'chinomethionate, aba; adam (abamectin ), metaflumizone, flubendiamide 'chlorantraniliprole' and 0-pyrene flumasone (pyrifluquinazon). Examples of the insect repellent active ingredient include 3,4-caranediol, N,N-diethyl-m-toluidine, 2-(2-hydroxyethyl)-1 1-methylpropyl piperidine carboxylic acid, p-menthane-3, 8-diol and plant essential oils such as hyssop oi 1 . Examples of hydrazine synergists include bis-(2,3,3,3-tetrachloropropyl)ether (S-421), N-(2-ethylhexyl)bicyclo[2.2.1]hept-5-ene -2,3-dimethylanimine (MGK-264) and α-[2-(2-butoxyethoxy)ethoxy]-4, 5-indenylenedioxy-2-propyl Toluene (piperonyl butoxide). Examples of nematicides, soil disease pest control agents, mold removers and herbicides include conventional practitioners. EXAMPLES Hereinafter, the present invention will be further illustrated by way of Production Examples, Formulation Examples and Test Examples, but the present invention is not limited thereto. First, a production example of the compound of the present invention will be described. Production Example 1 174 mg (mg) (0.91 mmol (mmol)) of 1-ethyl-(3-methylaminopropyl) cleaveramide hydrochloride and 5 mg (mg) of 4- Dimethylaminopyridine was added to 166 mg (0.76 mmol) of 4~(2-propynyl)-2,3,5'6-tetrafluorobenzyl alcohol and 150 mg (〇.91 mil). (1R)-D-Difluoromethyl-2,2-dimethylcyclopropanone in 5 ml (mi) of chloroform dissolved in 320796 29 200934388, and the mixture was stirred at room temperature for 18 hours. . Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was dried with MgSO.sub. The residue was subjected to silica gel column chromatography [product name: si He gel, 60N (spherical, neutral), Kant〇 Chemical c〇., inc. to obtain 166 I g (10) one inverse _3 _二的methyl-cyclopropanecarboxylic acid 4-(2-propynyl)-2, 3, 5, 6-tetrafluoromethane methyl ester':

CF2H (Compound (1) of the present invention) (hereinafter referred to as the compound (1) of the present invention) is a clear colorless liquid.士-眶 (CDC13) “ppm” : h26 (3H, s), 128 1.80-1.82 (1H, m), 1.88-1.96 (iH, m), 2. 〇7-2 08 (1^ mX 3*65 (2H^^J=1-3H^ 5-25(2H, s), 5.61 〇h, d; J=6. 1,55. 9Hz). Manufacturing Example 2 ο 335 gram (mg) (1 .75 millimoles of 1-ethyl-3-(3-dimethylpropyl)carbodiimide hydrochloride with 5 mg (mg) of 4-dimethylamine~= added with 273 mg (1·22 millimolar) of 4-methoxymethyl heart 5: 1,4-tetrahydrofuran with 240 mg (1.46 mmol) of 〇R)-anti-dione- 2,2-two In a 5 ml (iv) solution of methylcyclopropane acid, the mixture was stirred at room temperature for 18 hours. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The residue was subjected to silica gel column chromatography (product name: silica gel, neutral, neutral), manufactured by Kanto Chemical Co., Inc. 3〇 32〇796 30 200934388 g (1R) -trans-3-difluoromethyl-2,2-dimethylcyclopropanecarboxylic acid 4-methoxymethyl-2,3,5,6-tetrafluorobenzyl ester:

(The compound (2) of the present invention) (hereinafter referred to as the compound (2) of the present invention) is a clear colorless liquid. ^-NMR (CDCL·) (5 (ppm): 1.25 (3H, s), 1.28 (3H, s), 1.80-1.82 (1H, m), 1.88-1.95 (1H, m), 3.41 (3H, s ), ❹ 4. 59 (2H, s), 5· 26 (2H, m), 5. 63 (1H, dt, J=6.2, 55.9 Hz). Production Example 3 At 0 ° C, 0.3 ml ( 2. 30 millimoles of dimethylaminotrisulfide sulfur added to 400 mg (1.15 mmol) of (1R)-cis-3-carboxyl-2,2-didecyl ring A solution of 4-methoxymethyl-2,3,5,6-tetrafluorobenzoate of propanecarboxylate in 20 ml of chloroform, and the mixture was stirred at room temperature for 18 hours. _ Water was added to the reaction mixture, Subsequently, it was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was chromatographed by column chromatography [product name · · silica gel, 60N (spherical, neutral), Japan Kanto Chemical Co., Ltd. ( (manufactured by Kanto Chemical Co., Inc.) to obtain 179 mg of (1R)-cis-3-difluoromethyl-2,2-dimercaptocyclopropanecarboxylic acid 4-oxomethoxy as shown in the following formula Base-2, 3, 5, 6-tetrafluorobenzyl ester:

(Compound (3) of the present invention) 31 320796 200934388 s), s), (hereinafter referred to as the compound (3) of the present invention) is a clear colorless liquid. INMR (CDC13) 5 (卯m) : L24 (10), s), 133 (10) 1.56-1.80 (2H, ,), 3.41 (3H, s), 4. 59 (2H; 5. 21-5.29 (2H, m) , 6. 12-6.42 (1H, m). Production Example 4 is the same as the method of Production Example 3, but using (1 Magic_Shun_3_Methyl)

Dimercapto-propyl propyl carboxylic acid 4-(2-propynyl)_2, 3, 5, 6-tetrafluoro-benzoate 31 generation (110-cis_3_mercapto-2' 2-dimethyl ring Propylamine dimethoate-2,3,5,6-tetrafluorobenzoate, and (1R)_cis-3-oxide:methyl-2,2-dimercaptopropane as shown in the following formula 4-(2-propynyl)- 2, 3, 5 ^

F

(Compound (4) of the present invention) (hereinafter referred to as the compound (4) of the present invention) Intermediate of the compound ❹ Next, a method for producing the present invention will be described with reference to the production examples. Reference Manufacturing Example Step 1:

2. 1 ml (16.0 mmol) of dimethylaminosulfur trifluoride was added to 1.0 g (g) (6.40 mmol) of (1{^)_anti_3 at 〇 °C. _Mercapto-2,2-dimethylcyclopropane acid methyl ester in 15 ml (ml) chloroform solution 320796 32 200934388 and the mixture was allowed to stand at room temperature for 18 hours and 18 hours. Water is added to the reaction mixture. The organic layer was dried over magnesium sulfate and then reduced to <RTI ID=0.0>>>> Yes. Pressure concentration to obtain 926 g (1R) - anti-3 Methyl propyl decanoate: ) 6 (ppm): 1. 26 (3Η' s), 1. 28 (3Η, ^-NMR (CDCI3 ) d (όόπί'): 1 〇β (1.77-1.94 (2Η, m), 3.71 (3H, s), 5. 62(1H, dt, J=6 56·0Ηζ). Step 2:

926 mg (mg) (5.20 mmol) of methyl (1R)-trans-3~dimethyl-2,2-dimethylcyclopropanecarboxylate dissolved in 5 ml of methanol with 2 ml The mixture was mixed with a 5% aqueous sodium hydroxide solution and stirred at 100 ° C for 5 hours. Methyl tertiary butyl ether was added to the reaction mixture. After separation of the liquid layer, the aqueous layer was adjusted to pH 2 with 1 Nm acid, and then extracted with ethyl acetate. The obtained organic layer was dried (MgSO4) and evaporated. ^-NMR (CDCh) δ (ppm): 1.30 (3H, s), 1.31 (3H, s) 1. 59 (brs, 1H), 1. 83-1. 96 (2H, m), 5. 64 ( 1H, dt, J=6. 〇, 55.9 Hz) 0 The formulation example will be described below. All parts are by mass. Formulation Example 1 20 parts of any of the present compounds (1) to (4) were dissolved in xylene, and 15 parts of Sorpol 3005X (Toho Chemical 33320796 200934388 company (share)) (Toho Chemical C〇τ) was added thereto. , N 丄*, υ·, Ltd.), and thoroughly mix and mix the resulting mixture to obtain an emulsifiable concentrate. Formulation Example 2 In 40 parts of any of the present compounds (1) to (4), 5 parts of Sorpol 3GG5X' was added to thoroughly mix the resulting compound, and a portion of the drug was added to Carpiex Xia Synthetic Coin, Yanyeyi Pharmaceutical Co., Ltd. ( Shares) (registered trademark of Shionogi Phannaceutic M C〇., Ud) and (ii)

The wounded 3GG mesh, Shixiazao soil, was mixed and mixed with a juice mixer to obtain a wettable powder. Formulation Example 3 1.5 parts of any of the present compounds (1) to (4), aliquot

Tokuseal GUN (synthetic water oxidized oxide eve, manufactured by T〇kUyama c〇rp.) ‘ 2 injured Reax 85A (Lignin nitrite, West Vaco 〇

(manufactured by Chemicals) '30 parts of Bentonite Fuji (bentonite, manufactured by Hojun Corp.) was thoroughly ground together with a mixture of 65.5 parts of Shokozan A clay (kaolin, manufactured by Shokozan Kogyosho), and water was added thereto. The mixture was then thoroughly kneaded, granulated by a granulator, and dried to obtain 1.5% granules. Formulation Example 4 10 parts of any one of the present compounds (1) to (4), 1 part by weight of phenyldiphenylene phenylethane and 0.5 part of Sumijul L-75 (indole diphenyl cyanide) A mixture of Sumitomo (manufactured by Bayer Urethane Ltd.) was added to 20 parts of an aqueous solution of 1% alginate, followed by stirring with an emulsifier homogenizer to obtain an emulsion having an average particle diameter of 20 μm. This emulsion was further mixed with 2 parts of ethylene glycol of 320796 34 200934388, and the mixture was stirred in a warm bath of 60 ° C for 24 hours to obtain a microcapsule slurry. In addition, 0.2 parts of xanthan gum and 1 part by weight

Veegum R (manufactured by Sanyo Chemical Co., Ltd.) was dispersed in 56.3 parts of ion-exchanged water to obtain a thickener 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 1 part by weight of fluorenyl phenyl phenylethane is added to 2 parts of a 1% by weight aqueous solution of polyethylene glycol. Then, it was stirred with an emulsification homogenizer to obtain an emulsion having an average particle diameter of 3 μm. Separately, 0.2 parts of Huangyuan Kick and 1 part of Veegum R (manufactured by Sanyo Chemical Co., Ltd.) were dispersed in 58·8 parts of ion-exchanged water to obtain a solubilizer solution. Splendens 40 parts of the above emulsion was mixed with 60 parts of the thickener solution to obtain a flowable formulation. Formulation Example 6 5 parts of any of the compounds of the present invention (1) to (4), ❹ Carplex #80 (registered trademark of synthetic aqueous oxidized Co., Ud.), 〇 3 parts of 'Shionogi Pharmaceutical 3 parts of PAP (mixture of dish acid-isopropyl vinegar and diisopropyl phosphate) and mixture with fruit juice mixer mix and mix example 1 human I 7 parts of talc (300 mesh) mixed powder (dust) 10 Dissolving 0.1 parts of any of the deodorant kerosene of 89. 9 parts of the deodorant kerosene to dissolve the compound (1) to (4) of the present invention in a portion of methyl chloride, and the solution and the obtained oil solution . Formulation Example 8 320796 35 200934388 1 part of any one of the present compounds (1) to (4), 5 parts of dichloromethane is mixed with 34 parts of deodorized kerosene to dissolve, and the resulting solution is filled into an aerosol. In the container, a valve is attached to the container, and 60 parts of propellant (liquefied petroleum gas) is charged through the valve under pressure to obtain an oily aerosol. Formulation Example 9 0.6 part of any of the present compounds (1) to (4), 5 parts of dinonylbenzene, 3.4 parts of deodorized kerosene and 1 part of sorbitan monolaurate (Leodor SP-L10, Manufactured by Kao Co., Ltd., HLB: 8. 6) Mix and dissolve, fill the resulting solution with 50 parts of water into an aerosol container, attach the valve to the container, and load it through the valve under pressure. A propellant (liquefied petroleum gas) is obtained as an aqueous aerosol. The compound of the present invention (1) to (4) is dissolved in 20 ml of acetone, and the solution and 99.7 g of the insecticide coil substrate (incense material powder, The mixture of distiller's grains powder and wood flour mixed in a ratio of 4:3:3 is uniformly mixed and scrambled, 100 ml of water is added thereto, and the mixture is thoroughly kneaded, molded and dried to obtain a insecticide coil. . The solution of the solution is 0. 5 ml of the solution uniformly, and the solution is 0. 5 ml of the solution is evenly dissolved in a solution of 0.5 ml of the solution. Immersion 2. 5 cm x l. 5 cm and a thickness of 0.3 cm of electrothermal insecticide sheet substrate (hardening fine fibers containing a mixture of cotton wool and pulp into a plate shape) to obtain electrothermal insecticidal Tablets. Formulation Example 12 36 320796 200934388 • 3 parts of any of the inventive compounds (1) to (4>& deodorized kerosene, the resulting solution is placed in a polyvinyl chloride, and the liquid is absorbed into the liquid. It can be used to obtain the components for the liquid collection: the stolen and electric hot yellow device. The liquid absorption core can be obtained by curing with a binder and calcining, and the upper part can be used with a heater, and the sample 13 can be used. Any one of the compounds (1) to (4) of the present invention is dissolved in an appropriate amount of acetone, and the solution is impregnated with a 4 〇 cm x 4 0 cm porous ceramic plate having a thickness of L 2 cm to obtain a heated scenting agent. Formulation Example 14 100 μg (#g) of any of the present compounds (D to (4) was dissolved in an appropriate amount of acetone, and the solution was uniformly applied to a 2 cm x 2 cm filter paper having a thickness of 3 mm, and The acetone was air-dried to obtain a formulation which was volatile in the chamber/dish. The following test examples show that the compound of the present invention is effective as an active ingredient of the pest control composition. In the test examples, the following compounds were used as comparisons. Compound (1R)-trans-3-(2-methyl, propyl)-2,2-dimethylcyclopropanecarboxylic acid 4-(2-propynyl)-2, 3, 5, 6_tetrafluorobenzoate:

F

#CH=C(CH3)2 (The compound described in JP-A 61-207361, hereinafter referred to as Comparative < (A)). (1R)-trans- 2' 2' 3-trimethylcyclopropanecarboxylic acid 4-methyl as shown in the formula: 320796 37 200934388 fluorenyl-2,3,5,6-tetrafluorobenzyl ester:

(The compound described in JP-A 200-302590, hereinafter referred to as Comparative Compound (B)). (1R)-trans-3-difluoromethyl-2,2-dimethylcyclopropanecarboxylic acid 7-trifluorodecyl-2,3-dihydrobenzofuran-3-ester represented by the formula:

(The compound described in W081/02892, hereinafter referred to as comparative compound (1)). Test Example 1 The test was knocked down by Culex pi pi pens pa liens using a insecticide coil. A 1% (w/v) (w/v) test compound acetone solution was prepared. Then, a substrate of 0.3 g of the insecticide coil (manufactured by Yuai Katori) was uniformly impregnated with 0.15 ml of this acetone solution, and air-dried to prepare a test insecticide coil. Ignite one end of the test insecticide coil. After one minute, it is determined that the combustion has stabilized. The test insecticide coils were then placed on a 70 cm standroom floor on each side, and 20 female common adult mosquitoes were released into them. The test insecticide coil was burned indoors for 30 seconds and then taken out immediately. After 3 minutes, the number of knocked down mosquitoes was counted (1 repetition). The results are shown in Table 1. 38 320796 200934388 '[Table 1] Test compound mosquito knockdown number Compound (1) 19 of the present invention Compound (2) 20 Compound (3) 6 Comparative compound (A) 8 Comparative compound (X) 0 ^ Test Example 2 An acetone solution of 0.005% (w/v) test compound was prepared. Ten female common adult mosquitoes were treated with the acetone solution at a dose of 0.015 gram of test compound per mosquito. Next, the water supply and feed are tested to the mosquitoes. After 24 hours, the number of dead mosquitoes was counted and the mortality was calculated (two replicates). The results are shown in Table 2〇 [Table 2] Test compound mortality (%) Compound of the present invention (2) 90 Comparative compound (B) 55 Industrial use The compound of the present invention has excellent pest control effect and thus can be used as a disease The active ingredient of the pest control composition. [Simple diagram] No 0 39 320796

Claims (1)

200934388 V· f VII. Scope of application for patents·· 1. A ciprofloxacin ester represented by formula (1): F In the formula, R1 represents a C2-C4 alkynyl group or a (C1-C4 alkoxy) anthracenyl group. 2. The cyclopropanecarboxylate of claim 1, wherein R1 is 2-propynyl or decyloxymethyl. 3. A pest control composition comprising the cyclopropane carboxylate of claim 1 as an active ingredient. 4. A method for controlling pests and diseases comprising administering an effective amount of the cyclopropanecarboxylate of claim 1 in a pest or pest habitat. ❹ 41 320796 200934388 IV. Designated representative map: There is no schema 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: F 320796