AU2010236006A1 - Harmful organisim-controlling composition and control method of harmful organisms - Google Patents

Description

Australian Patents Act 1990 - Regulation 3.2 ORIGINAL COMPLETE SPECIFICATION STANDARD PATENT Invention Title Harmful organism-controlling composition and control method of harmful organisms The following statement is a full description of this invention, including the best method of performing it known to me/us: P/00/0 11 5102 la BACKGROUND OF THE INVENTION 5 Field of the Invention [0001] The present invention relates to a pest control composition and a control method of pests. Description of the Related Art 10 [0002] An ester compound represented by the formula (I): F F H 3 C CH 3

H

3

COH

2 C CH=CCl 2 (I) - 0 F F 0 is known to be an effective ingredient of a pest control preparation (e.g., see JP 57-123146 A and CN 101306997 A). 15 Further, an ester compound represented by the formula (II) 0

H

3 C CH 3

CH=C(CH

3

)

2 (I

H

3 C 0 2 is also known to be an effective ingredient of a pest control preparation (e.g., see "Zoku Iyakuhin no Kaihatsu, vol. 18, Noyaku no Kaihatsu III (The Second Series of Pharmaceutical Research and Development, vol. 18, 5 Management and Development of Agrochemicals III)", Hirokawa Publishing Company, 1993, p. 493-514). [0003] However, in some cases, a pest control preparation having a superior controlling effect to such a known 10 preparation is required depending on particular application and pests to be controlled. SUMMARY OF THE INVENTION Problems to be Solved by the Invention [0004] 15 An object of the present invention is to provide a pest control composition and a control method having an excellent control effect on pests. Means for Solving the Problems [0005] 20 As a result of the present inventor's intensive study, it has been found that combination use of the ester compound represented by the formula (I) and the ester compound represented by the formula (II) exhibits excellent control effect on pests. Thus, the present invention has 25 been completed.

3 [00061 That is, the present invention provides: (1) a pest control composition which comprises as effective ingredients a combination of an ester compound 5 represented by the formula (I): F F H3C CH 3

H

3 C0H 2 C CH=CCl 2 -- 0 F F 0 (hereinafter referred to as the present ester compound A) and an ester compound represented by the formula (II): 0

H

3 C

CH

3

CH=C(CH

3

)

2

H

3 C 0 0 10 (hereinafter referred to as the present ester compound B); (2) the pest control composition according to the above (1) (hereinafter referred to as the present control composition), wherein the weight ratio of the present ester compound A to the present ester compound B is within the 15 range of from 50 : 1 to 1 : 50; (3) a control method of pests which comprises applying an effective amount of a combination of the 4 present ester compound A and the present ester compound B to pests or areas where pests live; and (4) use of a combination of the present ester compound A and the present ester compound B for controlling 5 pests. Effects of the Invention [0007] The present control composition and the control method exhibit an excellent control effect on pests. 10 DETAILED DESCRIPTION OF THE INVENTION [0008] The present control composition is characterized in that it contains both the present ester compound A and the present ester compound B. 15 The present ester compound A can be produced, for example, by a process described in JP 57-123146 A. [0009] The present ester compound B can be produced, for example, by a process described in JP 49-054529 A. 20 [0010] Each of the present ester compound A and the present ester compound B has isomers based on two asymmetric carbon atoms on its cyclopropane ring. In the present invention, the ester compound containing the active isomers in any 25 ratios can be used.

5 [00:11] Examples of the pests against which the present control composition exhibits a controlling effect include harmful arthropods such as insect pests and acarine pests. 5 Specific examples thereof are as follows. [0012] Lepidoptera insect pests: Pyralid moths (Pyralidae) such as rice stem borer (Chilo suppressalis), rice leafroller (Cnaphalocrocis 10 medinalis), and Indian meal moth (Plodia interpunctella); owlet moths (Noctuidae) such as common cutworm (Spodoptera litura), beet armyworm (Spodoptera exigua), rice armyworm (Pseudaletia separata), and cabbage armyworm (Mamestra brassicae); white butterflies (Pieridae) such as common 15 white (Pieris rapae); tortricid moths (Tortricidae) such as Adoxophyes spp.; fruitworm moths (Carposinidae); lyonetiid moths (Lyonetiidae); tussock moths (Lymantriidae); Plusiae; Agrotis spp. such as cutworm (Agrotis segetum) and bluck cutworm (Agrotis ipsilon); Helicoverpa spp.; Heliothis 20 spp.; diamondback (Plutella xylostella); common straight swift (Pamara guttata); casemaking clothes moth (Tinea translucens); and webbing clothes moth (Tineola bisselliella). Diptera insect pests: 25 Mosquitos (Calicidae) such as common mosquito (Culex 6 pipiens pallets), Culex tritaeniorhynchus, and Southern house mosquito (Culex quinquefasciatus); Aedes spp. such as yellow fever mosquito (Aedes aegypti), and Asian tiger mosquito (Aedes albopictus); Anopheles spp. such as 5 Anopheles sinensis; midges (Chironomidae); houseflies (Muscidae) such as housefly (Musca domestica, Musca bezzi, false stable fly (Muscina stabulans), and lesser housefly (Fannia canicularis); blow flies (Calliphoridae); flesh flies (Sarcophagidae); anthomyiid flies (Anthomyiidae) such 10 as seedcorn maggot (Delia platura), and onion maggot (Delia antiqua); black scavenger flies (Sepidae); fruit flies (Tephritidae); leaf-miner flies (Agromyzidae); small fruit flies (Drosophilidae) such as common fruit fly (Drosophila melanogaster); moth flies (Psychodidae); Phorid flies 15 (Phoridae) such as humpbacked fly (Megasalia spiracularis); black flies (Simuliidae) ; horse flies (Tabanidae); stable flies (Stomoxyidae); and biting midges (Ceratopogonidae). Dictyoptera insect pests: Cockroaches (Blattariae) such as German cockroach 20 (Blattella germanica) , smokybrown cockroach (Periplaneta f uliginosa) , American cockroach (Periplaneta americana) , blown cockroach (Periplaneta brunnea), and oriental cockroach (Blatta orientalis). Hymenoptera insect pests: 25 Ants (Formicidae); hornets (Vespidae); Bethylid wasps 7 (Betylidae); and sawflies (Tenthredinidae) such as cabbage sawfly (Athalia rosae). Aphaniptera insect pests: Dog flea (Ctenocephalides canis), cat flea 5 (Ctenocephalides feils), and human flea (Purex irritans). Anoplura insect pests: Human louse (PediCulus humans), crab louse (Phthirus pubis), head louse (Pediculus humans capitis), and human body louse (Pediculus humanus corporis). 10 Isoptera insect pests: Japanese subterranean termite (Reticulitermes speratus), and Formosan subterranean termite (Coptotermes formosanus) . Hemiptera insect pests: 15 Planthoppers (Delphacidae) such as small brown planthopper (Laodelphax striatellus), brown rice planthopper (Nilaparvata lugens), and white-backed rice planthopper (Sogatella furcifera); leafhoppers (Deltocephalidae) such as green rice leafhopper 20 (Nephotettix cincticeps), and Taiwan green rice leafhopper (Nephotettix virescens); aphids (Aphididae); stink bugs (Pentatomidae); whiteflies (Aleyrodidae) ; scales (Coccidae); cimices such as Cimex lectularius; lace bugs (Tingidae); and psyllids (Psyllidae). 25 Coleoptera insect pests: 8 Corn root worms (Diabrotica spp.) such as black carpet beetle (Attagenus japonicus), varied carpet beetle (Anthreus verbasci), Western corn root worm (Diabrotica virgifera virgifera), and Southern corn root worm 5 (Diabrotica undecimpunctata howardi); scarabs (Scarabaeidae) such as cupreous chafer (Anomala cuprea), and soybean beetle (Anomala rufocuprea); weevils (Curculionidae) such as maize weevil (Sitophilus zeamais), rice water weevil (Lissorhoptrus oryzophilus), boll weevil 10 (Anthonomus grandis), and azuki bean weevil (Callosobruchus chinensis); darkling beetles (Tenebrionidae) such as yellow mealworm (Tenebrio molitor), and red flour beetle (Tribolium castaneum); leaf beetles (Chrysomelidae) such as rice leaf beetle (Oulema oryzae), striped flea beetle 15 (Phyllotreta striolata), and cucurbit leaf beetle (Aulacophora femoralis); drugstore beetles (Anobiidae); Epilachna spp. such as twenty-eight-spotted ladybird (Epilachna vigintioctopunctata); powder post beetles (Lyctinae); false powder post beetles (Bostrichidae); 20 longhorn beetles (Cerambycidae); and rove beetle (Paederus fuscipes) . Thysanoptera insect pests: Melon thrips (Thrips palmi), yellow citrus thrips (Frankliniella occidentalis), and flower thrips 25 (Frankliniella intonsa).

9 Orthoptera insect pests: Mole crickets (Gryllotalpidae), and grasshoppers (Acrididae). Acarina: 5 House dust mites (Pyroglyphidae) such as Der7atophagoides farinae,' and Dermatophagoides ptrenyssnus; Acarid mites (Acaridae) such as mold mite (Tyrophagus putrescentiae), and Aleurogrlyphus ovatus; Glycyphagid mites such as Glycyphagus privatus, Glycyphagus domesticus, and 10 Glycyphagus destructgor; Cheyletide mites (Cheyletidae) such as Cheyletus malaccensis, and Cheyletus fortis; Tarsonemid mites (Tarsonemidae); Chortoglyphid mites (Chortoglyphidae); Haplochthoniid mites (Haplochthoniidae); spider mites (Tetranychidae) such as two-spotted spider 15 mite (Tetranychus urticae), Kanzawa spider mite (Tetranychus kanzawai) , citrus red mite (Panonychus citri), and European red mite (Panonychus ulmi); ticks (Ixodidae) such as Haemaphysalis longicornis; and parasitoid mites (Dermanyssidae) such as northern fowl mite (Ornithonyssus 20 sylviarum) , and poultry red mite (Dermanyssus gallinae). [0013] In particular, the present control composition exhibits excellent control effect on Diptera insect pests, more excellent control effect on mosquitos (Calicidae). 25 [0014] 10 In the present control composition, the weight ratio of the present ester compound A to the present ester compound B is not specifically limited as far as the excellent control effect of the present invention is 5 maintained. Usually, the weight ratio is within the range of from 50 : 1 to 1 : 50, preferably from 10 : 1 to 1 : 10. [0015] The present control composition can be a simple mixture of the present ester compound A and the present 10 ester compound B. However, it is usually used in the form of various formulations. Examples of the formulations include oil solution, emulsifiable concentrate, wettable powder, suspension concentrate (e.g. suspension in water, and emulsion in water), microcapsule formulation, dust, 15 granule, tablet, aerosol, carbon dioxide formulation, heating vaporization formulation (e.g. mosquito coil, electric mosquito mat, and fluid absorption wicking-type pesticide), piezo-type spray insecticide, heating fumigant (e.g. self-burning fumigant, chemical reaction type 20 fumigant, and porous ceramic plate fumigant), non-heating fumigant (e.g. resin fumigant, paper fumigant, unwoven fabric fumigant, woven fabric fumigant, and sublimation tablet), smoking formulation (e.g. fogging), direct contact formulation (e.g. sheet type contact formulation, tape type 25 contact formulation, and net type contact formulation), ULV 11 formulation, and poison bait. [0016] The formulation can be prepared, for example, by the following methods. 5 (1) The present ester compound A and the present ester compound B are mixed with a solid carrier, a liquid carrier, a gaseous carrier or feed and, if necessary, other auxiliary agents for formulations such as a surfactant. (2) A base material is impregnated with the present 10 ester compound A and the present ester compound B. (3) The present ester compound A, the present ester compound B and a base material are mixed, followed by molding. These formulations usually contain as a total amount 15 0.001 to 98% by weight of the present ester compound A and the present ester compound B. [0017] Examples of the solid carrier used for the formulation include fine powders and granules such as clays (e.g. 20 kaolin clay, diatomaceous earth, bentonite, Fubasami clay, and acidic white clay) , synthetic hydrated silicon oxide, talc, ceramics, other inorganic minerals (e.g. sericite, quarts, sulfur, active carbon, calcium carbonate, and hydrated silica), and chemical fertilizers (e.g. ammonium 25 sulfate, ammonium phosphate, ammonium nitrate, ammonium 12 chloride, and urea); and solid materials at ordinary temperature (e.g. 2,4,6-triisopropyl-1,3,5-trioxane, naphthalene, p-dichlorobenzene, camphor, and adamantane) as well as felt, fibers, cloth, woven fabrics, sheets, paper, 5 threads, foam, porous materials and multifilaments composed of one or more of wool, silk, cotton, hemp, pulp, synthetic resins (e.g. polyethylene resins such as low-density polyethylene, linear low-density polyethylene, and high density polyethylene; ethylene-vinyl ester copolymers such 10 as ethylene-vinyl acetate copolymer; ethylene-methacrylate copolymers such as ethylene-methyl methacrylate copolymer, and ethylene-ethyl methacrylate copolymer; ethylene acrylate copolymers such as ethylene-methyl acrylate copolymer, and ethylene-ethyl acrylate copolymer; ethylene 15 vinyl carboxylate copolymers such as ethylene-acrylic acid copolymer; ethylene-tetracyclododecene copolymer; polypropylene resins such as propylene homopolymer, and propylene-ethylene copolymer; poly-4-methylpentene-1; polybutene-1; polybutadiene; polystyrene; acrylonitrile 20 styrene resin; styrene elastomers such as acrylonitrile butadiene-styrene resin, styrene-conjugated diene block copolymer, and hydrogenated styrene-conjugated diene block copolymer; fluorine plastics; acrylic resins such as polymethyl methacrylate; polyamide resins such as nylon 6, 25 and nylon 66; polyester resins such as polyethylene 13 terephthalate, polyethylene naphthalate, polybutylene terephthalate, and polycyclohexylene dimethyleneterephthalate; polycarbonate; polyacetal; polyacrylsulfone; polyarylate; polyhydroxybenzoate; 5 polyetherimide; polyestercarbonate; polyphenylene ether resin; polyvinyl chloride; polyvinylidene chloride; polyurethane; and porous resins such as foamed polyurethane, foamed polypropylene, and foamed polyethylene), glass, metals, and ceramics. 10 [0018] Examples of the liquid carrier include aromatic or aliphatic hydrocarbons (e.g. xylene, toluene, alkyl naphthalene, phenylxylylethane, kerosene, light oil, hexane, and cyclohexane), halogenated hydrocarbons (e.g. 15 chlorobenzene, dichloromethane, dichloroethane, and trichloroethane), alcohols (e.g. methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, and ethylene glycol), ethers (e.g. diethylether, ethylene glycol dimethyl ether, diethylene glycol monomethyl ether, 20 diethylene glycol monoethyl ether, propylene glycol monomethyl ether, tetrahydrofuran, and dioxane), esters (e.g. ethyl acetate, and butyl acetate), ketones (e.g. acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone), nitriles (e.g. acetonitrile, and 25 isobutyronitrile), sulfoxides (e.g. dimethyl sulf oxide), 14 acid amides (e.g. N,N-dimethylformamide, N,N dimethylacetoamide, and N-methyl-pyrrolidone), alkylidene carbonates (e.g. propylene carbonate), vegetable oils (e.g. soybean oil, and cotton oil), vegetable essential oil (e.g. 5 orange oil, hyssop oil, and lemon oil) and water. [0019] Examples of the gaseous carrier include butane gas, chlorofluorocarbon gas, liquefied petroleum gas (LPG), dimethyl ether, and carbon dioxide. 10 [0020] Examples of the surfactant include alkyl sulfate ester salts, alkyl sulfonates, alkylaryl sulfonates, alkylaryl ethers, polyoxyethylenated alkylaryl ethers, polyethylene glycol ethers, polyhydric alcohol esters, and sugar alcohol 15 derivatives. [0021] Examples of other auxiliary agents for formulations include binders, dispersants, and stabilizers. Specific examples thereof include casein, gelatin, polysaccharides 20 (e.g. starch, gum arabic, cellulose derivatives, and arginic acid), lignin derivatives, bentonite, saccharides, synthetic water-soluble polymers (e.g. polyvinyl alcohol, polyvinyl pyrrolidone, and polyacrylic acid), BHT (2,6-di t-butyl-4-methylphenol), and BHA (mixture of 2-t-butyl-4 25 methoxyphenol and 3-t-butyl-4-methoxyphenol).

15 [0022] Examples of the base material of a mosquito coil include a mixture of plant powder (e.g. wood powder, and pyrethrum) and a binder (e.g. powder of Machilus thunbergii, 5 starch, and gluten). Examples of the base material of an electric mosquito mat include cotton linter matted, condensed and pressed in a plate shape, and mixed fibrils of cotton linter and pulp matted, condensed and pressed in a plate shape. 10 Examples of the base material of a self-burning fumigant include combustion heat-developing agents such as nitrates, nitrites, guanidine salts, potassium chlorate, nitrocellulose, ethyl cellulose, and wood powder; heat decomposition stimulating agents such as alkali metal salts, 15 alkaline earth metal salts, bichromates, and chromates; oxygen suppliers such as potassium nitrate; combustion supporting agents such as melamine, and wheat starch; fillers such as diatomaceous earth; and binders such as synthetic adhesives. 20 [0023] Examples of the base material of a chemical reaction type fumigant include heat-developing agents such as sulfide, polysulfide, and hydrosulfide of alkali metals, and calcium oxide; catalysts such as carbonaceous materials, 25 iron carbide, and activated clay; organic foaming agents 16 such as azodicarbonamide, benzenesulfonyl hydrazide, dinitro pentamethylene tetramine, polystyrene and polyurethane; and fillers such as natural fibers and synthetic fibers. 5 [0024) Examples of the resin used for, for example, a resin fumigant include polyethylene resins such as low-density polyethylene, linear low-density polyethylene, and high density polyethylene; ethylene-vinyl ester copolymers such 10 as ethylene-vinyl acetate copolymer; ethylene-methacrylate copolymers such as ethylene-methyl methacrylate copolymer, and ethylene-ethyl methacrylate copolymer; ethylene acrylate copolymers such as ethylene-methyl acrylate copolymer, and ethylene-ethyl acrylate copolymer; ethylene 15 vinyl carboxylate copolymers such as ethylene-acrylic acid copolymer; ethylene-tetracyclododecene copolymer; polypropylene resins such as propylene homopolymer, and propylene-ethylene copolymer; poly-4 -methylpentene-1; polybutene-1; polybutadiene; polystyrene; acrylonitrile 20 styrene resin; styrene elastomers such as acrylonitrile but:adiene-styrene resin, styrene-conjugated diene copolymer, and hydrogenated styrene-conjugated diene block copolymer; fluorine plastics; acrylic resins such as polymethyl methacrylate; polyamide resins such as nylon 6, and nylon 25 66; polyester resins such as polyethylene terephthalate, 17 polyethylene naphthalate, polybutylene terephthalate, and polycyclohexylene dimethyleneterephthalate; polycarbonate; polyacetal; polyacrylsulfone; polyarylate; polyhydroxybenzoate; polyetherimide; polyestercarbonate; 5 polyphenylene ether resin; polyvinyl chloride; polyvinylidene chloride; and polyurethane. They can be used alone or in a combination thereof. Further, if necessary, plasticizer such as phthalates (e.g. dimethyl phthalate, and dioctyl phthalate), adipates, and stearic 10 acid can be added to these base materials. The resin fumigant is prepared by kneading the present ester compound A and the present ester compound B into the base material, followed by molding it by injection molding, extrusion molding or press molding. The resultant resin formulation 15 can undergo further processes such as molding and cutting, if necessary, processing into a form of plate, film, tape, net: or string. These resin formulations can be processed into, for example, collars for animals, ear tags for animals, sheet formulations, guide strings and 20 horticultural supports. [0025] Examples of the base material for poison bait include feed ingredients such as grain powder, vegetable oil, sugars, and crystalline cellulose; antioxidants such as 25 dibutylhydroxy toluene, and nordihydroguaiaretic acid; 18 preservatives such as dehydroacetic acid; accidental ingestion prevention agents by children and pets such as chili pepper; and pest attractive flavors such as cheese flavor, onion flavor, and peanut oil. 5 [0026] The control method of pests of the present invention is carried out by applying the present control composition to pests and/or to areas where pests live (e.g., plant body, soil, indoor, and animal body). Further, the control 10 method of pests of the present invention can also be carried out by separately applying the present ester compound A and the present ester compound B to pests and/or to areas where pests live. Specifically, as the application method of the present 15 control composition, the following methods can be exemplified, and these methods can be appropriately selected according to, for example, the form of the control composition, and the application place. (1) The present control composition is applied as it 20 is to pests and/or areas where pests live. (2) The present control composition is diluted with a solvent such as water, followed by applying to pests and/or areas where pests live. In this case, usually, the present control composition 25 in the form of, for example, emulsifiable concentrate, 19 wettable powder, suspension concentrate or microcapsule preparation is diluted so that the total concentration of the present ester compound A and the present ester compound B becomes 0.01 to 1000 ppm. 5 (3) The present control composition is heated at areas where pests live to vaporize the effective ingredients. In this case, the applied rate and concentration of the present ester compound A and the present ester compound B can be appropriately determined according to, for 10 example, the form of the present control composition, the application period, the application place, the application method, and the conditions of damage. [0027] In utilizing the present control composition for 15 preventative purpose, the application rate is usually from 0.0001 to 1000 mg/m 3 in terms of the total amount of the present ester compound A and the present ester compound B when applied to space, while it is from 0.0001 to 1000 mg/m 2 when applied to plane. The heating vaporization 20 formulation such as mosquito coil and electric mosquito mat is applied by appropriately heating according to the form of the formulation to vaporize the effective ingredients. The non-heating fumigant such as resin fumigant, paper fumigant, tablet, unwoven fabric fumigant, woven fabric 25 fumigant, and sheet formulation can be used, for example, 20 by leaving the formulation as it is at the place to be applied, or by making a wind toward the formulation. Examples of the place wherein the present control composition is applied for preventative purpose include 5 closet, dresser, chest, wardrobe, cupboard, toilet, bathroom, storeroom, living room, dining room, warehouse, and inside a car. Further, the composition can also be applied to outside open space. When the present control composition is used to 10 livestock such as cows, horses, pigs, sheep, goats and chickens, and small animals such as dogs, cats, rats and mice, for the purpose of controlling external parasites, veterinary known methods are applied to the animals. Specifically, the formulation is administered by way of 15 tablet, mixing in feed, suppository and injection (including intramuscular, subcutaneous, intravenous and intraperitoneal injections), when systemic control is intended. On the other hand, it is used by way of spraying the oil solution or aqueous solution, pour-on or spot-on 20 treatment, washing an animal with a shampoo formulation, or putting a collar or ear tag made of the resin formulation to an animal, when non-systemic control is intended. The total dosage of the present ester compound A and the present ester compound B is usually in the range from 0.01 25 tc 1000 mg per 1 kg of an animal body.

21 [00.29] The present control composition can be used in combination with, or as a mixture with other ingredients, for example, pest control agents such as other insecticides, 5 acaricides, and repellents, synergists, and pigments. [0030] Hereinafter, the present invention will be described in more detail by way of Formulation Examples and Test Examples. However, the present invention is not limited 10 thereto. First, Formulation Examples of the present control composition will be described. In the Formulation Examples, all the "parts" are by weight unless otherwise stated. [0031] 15 Formulation Example 1 In 37.5 parts of xylene and 37.5 parts of N,N dimethylformamide, 9 parts of the present ester compound A and 0.9 part of the present ester compound B are dissolved. To the resultant solution, 9.1 parts of polyoxyethylene 20 styryl phenyl ether and 6 parts of dodecylbenzenesulfonic acid calcium salt are added, followed by thoroughly mixing to obtain an emulsifiable concentrate. [0032] Formulation Example 2 25 To 20 parts of the present ester compound A and 20 22 parts of the present ester compound B, 5 parts of SORPOL 5060 (registered trademark of TOHO Chemical Industry Co., Ltd.) is added, followed by thoroughly mixing. To the resultant mixture, 32 parts of CARPLEX #80 (registered 5 trademark of Shionogi & Co., Ltd., dust of synthetic hydrated silicon oxide) and 23 parts of 300 mesh diatomaceous earth are added, followed by mixing with a juice mixer to obtain a wettable powder. [0033] 10 Formulation Example 3 To 3 parts of the present ester compound A and 0.3 part of the present ester compound B, 5 parts of dust of synthetic hydrated silicon oxide, 5 parts of dodecylbenzenesulfonic acid sodium salt, 30 parts of 15 bentonite and 56.7 parts of clay are added, followed by thoroughly stirring and mixing. Then, an appropriate amount of water is added to the resultant mixture. The mixture is further stirred, granulated with a granulator, and air-dried to obtain a granular formulation. 20 [0034] Formulation Example 4 In a mortar, 5 parts of the present ester compound A, 0.5 part of the present ester compound B, 1 part of dust of synthetic hydrated silicon oxide, 1 part of DORILES B 25 (trade name, manufacture by Daiichi Sankyo Co., Ltd.) as a 23 flocculating agent and 7 parts of clay are thoroughly mixed, followed by stirring and mixing with a juice mixer. To the resultant mixture, 85.5 parts of cut clay is added, followed by thoroughly stirring and mixing to obtain a dust 5 formulation. [0035] Formulation Example 5 A mixture of 10 parts of the present ester compound A, 1 part of the present ester compound B, 35 parts of white 10 carbon containing a half amount of polyoxyethylene alkyl ether sulfate ammonium salt, and 54 parts -of water are finely ground by a wet grinding method to obtain a dust formulation. [0036] 15 Formulation Example 6 In 10 parts of dichloromethane, 0.05 part of the present ester compound A and 0.1 part of the present ester compound B are dissolved, and the resultant solution is mixed with 89.85 parts of an isoparaffin solvent (ISOPAR M, 20 registered trademark of Exxon Chemical Co., Ltd.) to obtain an oil solution. [0037] Formulation Example 7 Into an aerosol can, 0.1 part of the present ester 25 compound A, 0.05 part of the present ester compound B, and 24 49.85 parts of Neothiozole (Chuo Kasei Co., Ltd.) are placed. After mounting an aerosol valve, 25 parts of dimethylether and 25 parts of LPG are filled, followed by shaking and further mounting an actuator to obtain an oily 5 aerosol. [0038] Formulation Example 8 A mixture of 0.5 part of the present ester compound A, 0.05 part of the present ester compound B, 0.01 part of BHT, 10 5 parts of xylene, 3.44 parts of deodorized kerosine and 1 part of an emulsifier (Atomos 300, registered trademark of Atomos Chemical Co., Ltd.), and 50 parts of distilled water are filled into an aerosol container, and a valve part is attached. Then, 40 parts of a propellant (LPG) is filled 15 thereinto through the valve under pressure to obtain an aqueous aerosol. [0039] Formulation Example 9 A piece of paper work of 0.5 cm thick, 69 cm length 20 and 0.2 cm wide which has a honeycomb structure is rolled up from one end thereof to prepare a cylindrical carrier of 5.5 cm diameter and 0.2 cm high. An appropriate amount of a solution prepared by dissolving 5 parts of the present ester compound A and 0.5 part of the present ester compound 25 B in 94.5 parts of acetone is uniformly applied on the 25 above carrier, and acetone is evaporated by air-drying to obtain a paper vaporization formulation. [0040] Formulation Example 10 5 A three dimensional knitted fabric (trade name: FUSION, model number: AKE69440, dealer: Asahi Kasei Fibers Corporation, thickness: 4.3 mm, fiber density: 321 g/m 2 , made of polyamide) is cut in a round shape of 5 cm diameter. An appropriate amount of a solution prepared by dissolving 10 5 parts of the present ester compound A and 0.5 part of the present ester compound B in 94.5 parts of acetone is uniformly applied on the above round three dimensional knitted fabric, and acetone is evaporated by air-drying to obtain a knitted fabric vaporization formulation. 15 [0041] Formulation Example 11 A mixture of 97.8 parts of an ethylene-methyl methacrylate copolymer (methyl methacrylate content: 10% by weight, MFR = 2[g/10 min.]), 2 parts of the present ester 20 compound A and 0.2 part of the present ester compound B are melted and kneaded with a 45 mm0 twin screw extruder rotating in the same direction at 130 0 C, and further melted and kneaded with a 40 mm0 extruder at 1500C, followed by extruding from a T die in a sheet shape, and cooling with a 25 cooling roll to obtain a resin vaporization formulation.

26 [0042] Formulation Example 12 A mixture of 97.8 parts of an ethylene-vinyl acetate copolymer (vinyl acetate content: 10% by weight, MFR = 5 2[g/10 min.]), 2 parts of the present ester compound A and 0.2 part of the present ester compound B are melted and kneaded with a 45 mm0 twin screw extruder rotating in the same direction at 130 0 C, and further melted and kneaded with a 40 mm0 extruder at 150'C, followed by extruding from 10 a T die in a sheet shape, and cooling with a cooling roll to obtain a resin vaporization formulation. [0043] Formulation Example 13 In 94.5 parts of acetone, 5 parts of the present ester 15 compound A and 0.5 part of the present ester compound B are dissolved. An appropriate amount of the resultant solution is applied on a paper having a foldable structure (2000 cm 2), and acetone is evaporated by air-drying to obtain a paper vaporization formulation. 20 [0044] Formulation Example 14 A solution is prepared by dissolving 3 parts of the present ester compound A and 0.3 part of the present ester compound B in 14.6 parts of acetone. To this solution, 0.2 25 part of zinc oxide, 1.0 part of a starch and 42.8 parts of 27 azodicarbonamide are added. Further, 38.1 part of water is added thereto, and the mixture is kneaded, molded in a granular shape with an extruder, and dried to obtain granules. In a container whose center portion is separated 5 by an aluminum partition, the granules are placed in the upper space thereof, and 50 g of calcium oxide is placed in the lower space thereof to obtain a fumigant. [0345] Formulation Example 15 10 To a mixture of 0.5 part of zinc oxide, 2 parts of a starch and 97.5 parts azodicarbonamide, water is added, and the mixture is kneaded and molded in a granular shape with an extruder, and dried to obtain granules. Then, 2 g of the granules are uniformly impregnated with a solution of 15 0.58 g of the present ester compound A and 0.058 g of the present ester compound B in acetone, and dried to obtain granules. In a container whose center portion is separated by an aluminum partition, the granules are placed in the upper space thereof, and 50 g of calcium oxide is placed in 20 the lower space thereof to obtain a fumigant. [0046] Formulation Example 16 In 20 mL of acetone, 0.5 g of the present ester compound A and 0.05 g of the present ester compound B are 25 dissolved, and the resultant solution is added to a mixture 28 of 99.4 g of a base material for a mosquito coil (a mixture of powder of Machilus thunbergii, pyrethrum and wood powder in the proportion of 4 : 3 : 3) and 0.3 g of green pigment. After thoroughly mixing, 120 mL of water is added to the 5 mixture and thoroughly kneaded. The resultant mixture is molded and dried to obtain a mosquito coil. [0047] Formulation Example 17 A solution is prepared by mixing 10 parts of the 10 present ester compound A, 1 part of the present ester compound B, 39.5 parts of acetyltributyl citrate, 39.5 parts of isononyl adipate, 5 parts of blue pigment and 5 parts of a flavor. A base material for an electric mosquito mat of 3.4 cm x 2.1 cm and 0.22 cm thick (matted, 15 concentrated and pressed fibrils of a mixture of cotton liter and pulp into a plate shape) is uniformly impregnated with the above solution to obtain an electric mosquito mat. [0048) 20 Formulation Example 18 A solution is prepared by dissolving 0.1 part of the present ester compound A and 0.01 part of the present ester compound B in 99.89 parts of deodorized kerosine. The solution is placed in a vinyl chloride container, and a 25 fluid absorption wick (prepared by firming an inorganic 29 powder with a binder and then sintering it) which is processed so as to be heated at its upper part with a heater is inserted therein to obtain a part of a fluid absorption wicking-type vaporization formulation. 5 [0049] Formulation Example 19 Into an aerosol can, 0.2 part of the present ester compound A, 0.02 part of the present ester compound B and 49.78 parts of Neothiozole (Chuo Kasei Co., Ltd.) are 10 placed. After mounting an aerosol valve, 25 parts of dimethylether and 25 parts of LPG are filled, followed by shaking and further mounting an actuator for whole content in:jection type aerosol to obtain an aerosol formulation. [0050] 15 Formulation Example 20 To 0.2 part of the present ester compound A and 0.02 part of the present ester compound B, 99.78 parts of diethylene glycol monoethyl ether is added, followed by thoroughly mixing to obtain a spot-on formulation for 20 controlling external parasites of animals. [0051] Formulation Example 21 A solution is prepared by dissolving 3 parts of the present ester compound A and 0.3 part of the present ester 25 compound B in 96.7 parts of acetone, and 1 mL of the 30 solution is uniformly applied on a disk shaped solid material (3 cm diameter and 3 mm thick) obtained by molding 4 g of 2,4,6-triisopropyl-1,3,5-trioxane under pressure (4 t/cm 2 ), followed by drying to obtain a tablet. 5 [0052] Formulation Example 22 A uniform mixture of 0.2 g of the present ester compound A, 0.02 g of the present ester compound B, and 4 g of 2,4,6-triisopropyl-1,3,5-trioxane is molded in a disk 10 shape (3 cm diameter and 3 mm thick) under pressure to obtain a tablet. [0053] Formulation Example 23 A mixture of 0.2 g of the present ester compound A, 15 0.02 g of the present ester compound B and 4 g of 2,4,6 triisopropyl-1,3,5-trioxane is placed in a 50 mL screw tube, heat-melted and then cooled to room temperature to obtain a tablet. [0054] 20 Then, the following Test Examples show that the present control composition has excellent controlling effect on pests. [0055] In the following Test Examples, as the present ester 25 compound A, [2,3,5,6-tetrafluoro-4- 31 (methoxymethyl)phenyl) methyl (1R) -trans-3- (2,2 dichlorovinyl) -2, 2-dimethylcyclopropanecarboxylate was used. Further, as the present ester compound B, (S)-2 methyl4-oxo-3- (2-propynyl) -2-cyclopentenyl (1R) -cis/trans 5 2,2 -dimethyl-3 - (2-methyl-l-propenyl) cyclopropanecarboxylate was used. [0056] Test Example 1 Oil solutions were prepared by diluting the present 10 ester compound B with given amounts of an isoparaffin solvent (ISOPAR M, registered trademark of Exxon Chemical Co., Ltd.) at concentrations as shown in the following Table 1 (hereinafter, referred to as Comparative Compositions (1) and (3)) . Similarly, the present ester 15 compound A was diluted with given amounts of an isoparaffin solvent (ISOPAR M, registered trademark of Exxon Chemical Co., Ltd.) to prepare oil solutions at concentrations as shown in Table 1 (hereinafter, referred to as Comparative Compositions (2) and (4)). 20 Further, the present ester compound A and the present ester compound B were diluted with given amounts of an isoparaffin solvent (ISOPAR M, registered trademark of Exxon Chemical Co., Ltd.) to prepare oil solutions at concentrations of the effective ingredients as shown in 25 Table 1 (hereinafter, referred to as Present Invention 32 Compositions (1) , (2) and (3)). [0057] In a cubic chamber having 70 cm sides, 10 Culex pipiens (female) were released, and 0.7 mL of Present 5 Invention Composition (1) was sprayed from a small window at the entrance of the chamber with a spray gun (spray pressure: 0.9 kg/cm 2 ) . At a given period of time after spraying, the number of knocked down insects was investigated and a knock down rate (KD rate) was calculated. 10 According to the same manner, KD rates after a given period of time were calculated by using Present Invention Compositions (2) and (3) and Comparative Compositions (1) to (4) (two runs). The results are shown in Table 1. 15 [0058] 33 Table 1 Content of the Content of the KD rate after 7 present ester present ester minutes compound A compound B (%) (w/v%) (w/v%) Present Invention 0.00313 0.00313 100 Composition (1) Comparative Composition - 0.00313 20 (1) Comparative Composition 0.00313 - 20 (2) Present Invention 0.00156 0.00313 50 Composition (2) Present Invention 0.00313 0.00156 50 Composition (3) Comparative Composition - 0.00156 10 (3) Comparative Composition 0.00156 10 ' _ (4) _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ [0059] Test Example 2 A base material for a mosquito coil (obtained by 5 stirring and mixing a mixture of powder of Machilus thunbergii, pyrethrum and wood powder in the proportion of 4 3 : 3, adding water thereto, thoroughly kneading the resultant mixture, followed by molding and drying) was uniformly treated with a given amount of an acetone 10 solution of the present ester compound B and air-dried to obtain a mosquito coil containing the compound at a concentration shown in the following Table 2 (hereinafter, referred to as Comparative Composition (5.)). Similarly, mosquito coils were obtained by using the present ester 34 compound A at concentrations shown in Table 2 (hereinafter, referred to as Comparative Compositions (6) and (7)). Further, the present ester compound A and the present ester compound B were diluted with given amounts of acetone 5 to obtain mosquito coils containing the compounds at concentrations shown in Table 2 (hereinafter, referred to as Present Invention Compositions (4) and (5)). [00603 In a cubic chamber having 70 cm sides, 0.5 g of 10 Present Invention Composition (4) was set on a mosquito coil stand placed on the bottom center thereof and was lit. After complete combustion of the mosquito coil, 20 Culex pipiens (female) were released from a small window at the entrance of the chamber. After a given period of time, the 15 number of knocked down insects was investigated and a knock down rate (KD rate) was calculated. According to the same manner, KD rates after a given period of time were calculated by using Present Invention Composition (5) and Comparative Compositions (5) to (7) (two runs). 20 The results are shown in Table 2. [0061] 35 Table 2 Content of the Content of the KD rate after 7 present ester present ester minutes compound A compound B (%) (wt%) (wt%)_ Present Invention 0.0025 0.025 65 Composition (4) Present Invention 0.005 0.025 80 Composition (5) Comparative Composition - 0.025 20 (5) Comparative Composition 0.0025 5 (6) Comparative Composition 0.005 25 (7) [0062] As described hereinabove, the present invention can provide a pest control composition and a pest control 5 method having excellent effect on pests. Throughout this specification and the claims which follow, unless the context requires otherwise, the word "comprise", and variations such as "comprises" and "comprising", will be understood to imply the inclusion of a stated integer or step or group of integers or steps but not the exclusion of any other integer or step or group of integers or steps. The reference in this specification to any prior publication (or information derived from it), or to any matter which is known, is not, and should not be taken as an acknowledgment or admission or any form of suggestion that that prior publication (or information derived from it) or known matter forms part of the common general knowledge in the field of endeavour to which this specification relates.

Claims (4)

1. A pest control composition which comprises as effective ingredients a combination of an ester compound represented by the formula (I): F F H 3 C CH 3 H 3 COH 2 C CH=CCl 2 (1) - 0 5 F F and an ester compound represented by the formula (II): O H 3 C CH 3 CH=C(CH 3 ) 2 H3CO 0

2. The pest control composition according to claim 1, wherein the weight ratio of the ester compound represented 10 by the formula (I) to the ester compound represented by the formula (II) is within the range of from 50 : 1 to 1 : 50.

3. A control method of pests which comprises applying an effective amount of a combination of an ester compound represented by the formula (I): 37 F F H 3 C CH 3 H 3 COH 2 C CH=CC 2 0 F F and an ester compound represented by the formula (II): 0 H 3 C OH 3 CH=C(CH 3 ) 2 H 3 C 0 0 to pests or areas where pests live. 5

4. Use of a combination of an ester compound represented by the formula (I): F F H 3 C CH 3 H 3 COH 2 C CH=CCl 2 - 0 F F and an ester compound represented by the formula (II): 0 H 3 C CH 3 CH=C(CH 3 ) 2 H 3 C 0 0