• 专利附录
  • 专利说明
  • 权利要求
  • 类似技术
  • 同族专利
  • 引用文献
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  • 优先权
    • 专利摘要:
    The pyrone compounds of formula 1 have an excellent effect in controlling harmful pests. Formula 1 In Formula 1 above, R is a trifluoromethyl group, a hydrogen atom or a methyl group.
    公开号:KR20020093570A
    申请号:KR1020020031315
    申请日:2002-06-04
    公开日:2002-12-16
    发明作者:후지나미미치히코
    申请人:스미또모 가가꾸 고교 가부시끼가이샤；
    IPC主号:
    专利说明:

    Pyrone compounds and their use}
    [1] The present invention relates to pyron compounds and their use as pesticides.
    [2] Japanese Laid-Open Patent Publication No. 51-19126 discloses that some pyron compounds have insecticide / caricide activity. However, these compounds are not effective to the extent that they are satisfactory in controlling harmful sea layer.
    [3] The present invention provides a compound of formula (1) and a pesticide composition comprising the same as an active ingredient, and a method for controlling pests, wherein the pesticide composition is applied to a pest or applied to a place where the pests reproduce.
    [4] The compounds of the present invention have excellent pesticidal activity.
    [5]
    [6] In Formula 1 above,
    [7] R is a trifluoromethyl group, a hydrogen atom or a methyl group.
    [8] The process for preparing the compounds of the present invention is described below.
    [9] The compounds of the present invention can be prepared by reacting the method shown in the following scheme, that is, 4-hydroxy-6-methyl-2-pyrone of formula (2) with a carboxylic acid of formula (3).
    [10]
    [11]
    [12]
    [13] In Scheme 1 above,
    [14] R is a trifluoromethyl group, a hydrogen atom or a methyl group.
    [15] This reaction is usually carried out in the presence of a condensing agent (eg dicyclohexylcarbodiimide) and 4-dimethylaminopyridine in dissolution.
    [16] Examples of solvents used in the reaction include aliphatic hydrocarbons such as hexane, heptane, octane and nonane, aromatic hydrocarbons such as toluene, xylene and mesitylene, halogenated hydrocarbons such as chlorobenzene, dichlorobenzene and benzotrifluoride, diisopropyl ether Ethers such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether and diethylene glycol dimethyl ether, acid amides such as N, N-dimethylformamide and N, N-dimethylacetamide, dimethyl sulfoxide and Sulfur-containing solvents such as sulfolane and mixtures thereof.
    [17] In the reaction, the proportion of the compound of formula 3 is 0.7 to 1.5 molar amount based on 1 mole of the compound of formula 2.
    [18] The proportion of the reagent is 1 to 5 moles of the condensing agent and 0.01 to 1 moles of 4-dimethylaminopyridine based on 1 mole of the compound of the formula (2).
    [19] The reaction temperature is usually in the range of 0 to 100 ° C., and the reaction time is usually 1 to 48 hours, although it depends on the reaction temperature.
    [20] After completion of the reaction, the reaction mixture can be filtered, for example, the filtrate is washed with acidic water, dried, concentrated and optionally purified by chromatography to afford the compounds of the invention as isolated products. have.
    [21] Examples of harmful pests in which the compounds of the present invention have a control effect include the following arthropods:
    [22] Semi-peptide pests: Delphacidae (Animalaceae) [for example, Laodelphax striatellus (Animalhopper), Nilaparvata lugens (Petocera) and Socatella purpur Sogatella furcifera (white back extinct)], Deltocephalidae (Cicada) [e.g., Nephotettix cincticeps, Nephotettix virescens and Les Recilia dorsalis], Aphididae (Aphidaceae), Stink bugs, Aleyrodidae (Gropiaceae), Beetles, Tingidae (Meteoraceae) and Psillida Psyllidae (Tropaceae),
    [23] Species Pests: Pyralidae (M. moth) [e.g. Chilo suppressalis (E. moth), Cnaphalocrocis medinalis (Black moth) And Plodia interpunctella (Hwarangok moth)], Noctuidae (chestnut moth) (eg, Spodoptera litura (tobacco spider moth), Sudaleti ce Pseudaletia separata (dystaglio moth), Mamestra brassicae (thief moth), Plusiinae (midnight moth), Agrotis segetum (macropod moth) And Agrotis spp., Helicobpa spp. And Heliothis spp., And Pierreidae, containing Agrotis ipsilon (arrested seminary) (The white butterfly family) (for example, Pieris rapae), Tortricidae ( Horse moth family) (eg, Adoxophyes spp.), Carposinidae (American moth), Lyoniteidae (Oyster moth), and Lehmantri. Lymantriidae (Poison moth), Yponameutidae (home moth) (for example, Flutella xylostella), Hesperiidae (Palangavidae) [ For example, Parnara guttata], Tineidae (grain moth) (for example, Tinea translucens (cloth moth) and Tyneola vituliella) (Tineola bisselliella)
    [24] Twin-peptide pests: Culex spp. (Eg, Culex pipiens pallens and Culex tritaeniorhynchus), Aedes spp. (Eg For example, Aedes aegypti (Egypt forest mosquito) and Aedes albopictus], Anopheles spp. (E.g., Anopheles sinensis). ], Chironomidae (Colcidae), Muscidae [e.g. Musca domestica (housefly), Muscina stabulans (doctor housefly) and plate Fannia canicularis (small housefly)], Califoridae, Sarcophagidae, Anthomyiidae [for example, Delia platura ( Sea Capricorn) and Delia antiqua (Capricorn)], Tephritidae (fruit onions) Family), Drosophilidae (Drosophila), Psychodidae (Mothfly), Tabanidae, Simuliidae (Mamparidae), Stompoxyidae ( Drosophila), Phoridae and Ceratopogonidae (Deer Mosquito),
    [25] Crop pests: Corn roots (for example Diabrotica virgifera (grain root worm) and Diabrotica undecimpunctata howardi (spotted cucumber leaf beetle)), Scarabeidae ) [For example Anomala cuprea and Anomala rufocuprea], Curculionidae (Weevilaceae) [for example, Sitophilus zeamais (Rice weed weevil) and Lissorhoptrus oryzophilus (rice weevil)], Dermestidae (e.g., Authrenus verbasci and Atagenus uni) Attagenus unicolor japonicus], Tenerbrionidae (eggum), for example Tenebrio molitor (brown grout) and Tribolium castaneum (false)Rice thief)], Chrysomelidae (Lepidaceae) [eg Oulema oryzae (leaf beetle), Phyllotreta striolata (leaven beetle) And Aulacophora femoralis (cucumber beetle)], Anobiidae (combine beetle), Coccinellidae (ladybug) [e.g. Octopunta vigintioctopunctata], Lyctidae (Tropaceae), Bostrychidae, Cerambycidae and Staphylinidae (eg Pae Derus puscipes],
    [26] Mantis Pests: Blattella germanica (German Cockroach), Periplaneta fuliginosa (cockroach), Periplaneta americana (US cockroach), Periplaneta Brunnea Periplaneta brunnea (Brown Cockroach) and Blata orientalis,
    [27] Total pests: Tripidae [e.g. Tripps palmi, Frankliniella occidentalis (cucumber larvae) and Tripps hawaiiensis (Hawaii borealis) )],
    [28] Maxima pests: Formicidae (antaceae), Vespidae (e.g. bumblebees and stilt wasps), Bethylidae and Tenthredinidae (Lepidoptera) ) [For example Athaliajaponica (cabbage leaf bee)],
    [29] Direct-infested Pests: Gryllotalpidae (Gropedidae) and Acrididae (Grassoptera),
    [30] Silver Pests: Ctenocephalides canis (dog flea), Ctenocepalidae felis (cat flea) and Pulex irritans (human flea),
    [31] Anopluran pests: Humanus corporis, Pediculus capitis and Phthirus pubis (slopes),
    [32] Isopod pests: Reticulitermes speratus and Coptotermes formosanus,
    [33] Mite pests: Tetranychidae (mite) (for example Tetranychus cinnabarinus (spotted mite), Tetranychus urticae (spotted mite), Tetranychus kanzawai (Cha Ngae), Panonychus citri (Cangtan Ngae) and Panonichus ulmi (Apple Ngae), Ixodidae [example Examples include Boophilus microplus and Haemaphysalis longiconis, Acaridae (eg Tyrophagus putrescentiae (long hair mite)). And Aleuroglyphus ovatus], Dermanyssidae [e.g., dermatophagoides farinae (American house dust mite) and dermatopagodes pternisus ( Dermatophagoides ptrenyssnus], Glycyphagidae [e.g., Glycyphagus privates, Glycyphagus domesticus and Glycyphagus destructor] , Cheyletidae (e.g., Cheyletus malaccensi and Cheyletus fortis), Tarsonemidae, Chortoglyphus spp .) And Haplochthonius spp.],
    [34] Isometric pests: wood louse (e.g. Porcellio scaber and Porcellionides pruinosus) and pill-bug (e.g. armadyl) Iridium vulgare].
    [35] The pesticide composition of the present invention comprises a compound of the present invention and an inert carrier such as a solid carrier, a liquid carrier, a gaseous carrier and / or a bait material (toxic feed material). The compound of the present invention can be impregnated into a substrate (eg, porous ceramic plate, nonwoven fabric, paper, mosquito-coil substrate). In addition, the pesticide composition of the present invention may optionally include a surfactant or other auxiliaries, including an oily solution, an emulsifiable concentrate, a wettable powder, a fluid formulation, a granule, a powder, an aerosol, an aerosol, a heating oxidizer, Iii), smokers, toxic feeds, microcapsule formulations, ULV formulations, spot-on formulations, pour-on formulations, shampoo formulations, sheet formulations, resin formulations, etc. Can be formulated.
    [36] Such formulations typically comprise the compound of the invention as an active ingredient in an amount of 0.01 to 95% by weight.
    [37] Examples of solid carriers used in the formulation include micropowders or granules of clay (e.g. kaolin clay, diatomaceous earth, synthetic hydrous silicon oxide, bentonite, Fuvasami clay, acid clay), talc, ceramics, fertilizers ( For example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ammonium chloride, urea) and other inorganic minerals (eg, sericite, quartz, sulfur, activated carbon, calcium carbonate, hydrous silicon oxide).
    [38] Examples of liquid carriers include water, alcohols (eg methanol, ethanol), ketones (eg acetone, methyl ethyl ketone), aromatic hydrocarbons (eg toluene, xylene, ethylbenzene, methylnaphthalene), aliphatic Hydrocarbons (eg hexane, chlorohexane, kerosene, diesel), esters (ethyl acetate, butyl acetate), nitriles (eg acetonitrile, isobutyronitrile), ethers (eg diisopropyl ether) , Dioxane), acid amides (e.g., N, N-dimethylformamide, N, N-dimethylacetamide), halogenated hydrocarbons (e.g., dichloromethane, trichloroethane, carbon tetrachloride), organic sulfur compounds ( For example, dimethyl sulfoxide) and vegetable oils (eg soybean oil, cottonseed oil) are included.
    [39] Examples of gaseous carriers include fluorocarbons, butane gas, LPG (liquefied petroleum gas), dimethyl ether and carbon dioxide.
    [40] Examples of surfactants include alkyl sulfates, alkyl sulfonates, alkylaryl sulfonates, alkyl aryl ethers, polyoxyethylenealkyl aryl ethers, polyethylene glycol ethers, polyhydric alcohol ethers and sugar alcohol derivatives.
    [41] Examples of other adjuvants include fixatives, dispersants and stabilizers, typically casein, gelatin, polysaccharides (eg starch, gum arabic, cellulose derivatives, alginic acid), lignin derivatives, synthetic water soluble polymers (eg polyvinyl) Alcohols, polyvinyl pyrrolidone, polyacrylic acid), PAP (acid isopropyl phosphate), BHT (2,6-di-tert-butyl-4-methylphenol), BHA (2-tert-butyl-4-methoxy Phenols and mixtures of tertiary butyl-4-methoxyphenol), vegetable oils, mineral oils, fatty acids and fatty acid esters.
    [42] Substrates for toxic foods include food ingredients (e.g., cereal meal, vegetable oil, sugar, cellulose), antioxidants (e.g. dibutylhydroxytoluene, nordihydroguaiaretic acid), preservatives (e.g. , Dehydroacetic acid), ingredients for preventing eating (e.g. red pepper powder) by children and pets, pest attractant flavors (e.g. cheese flavors, onion flavors, peanut oil).
    [43] When the pesticide composition of the present invention is used for the control of agricultural and forest pests, the dosage of the compound of the present invention is usually 1 to 10000 g per hectare. Emulsifiable concentrates, wettable powders and flowable formulations are applied by dilution with water to a concentration of 10 to 10000 ppm. Granules and powders are normally used as prepared. Such formulations may be applied directly to plants or to plants that are crops to be protected from pests. In addition, the formulation may be applied to the soil in order to control pests inhabiting the soil.
    [44] When the pesticide composition of the present invention is used for protection, the emulsifiable concentrate, the wettable powder, and the flowable formulation are diluted with water so as to have a concentration of 0.01 to 10000 ppm, and applied at the place where the pests or pests reproduce. Oily solutions, aerosols, smokers and toxic foods are applied as prepared to the pest or place where the insects reproduce. The heating transcriptant is applied by heating and volatilizing the active ingredient in a place where pests reproduce. The dosage of the compounds of the invention is typically from 0.001 to 5 g / m 2 at the bottom or from 0.01 to 10 g / m 3 at the bottom.
    [45] The insecticide composition of the present invention can be used with other insecticides, acaricides, nematicides, fungicides, herbicides, plant growth regulators, synergists, fertilizers, soil improvers, animal feeds and the like.
    [46] Examples of insecticides, acaricides and nematicides include organophosphorus compounds such as phenythrothione, pention, diazinon, chlorpyriphos, acetate, methiditaone, disulfotone, DDVP, sulfo Phos, cyanoforce, dioxabenzofoss, dimethoate, pentoate, malathion, trichlorphone, azineforce-methyl, monocrotophos and ethion; Carbamate compounds such as BPMC, benpracarb, propoxur, carbosulfan, carbaryl, methyl, thiophencarb, aldicarb, oxamyl and phenothiocarb; Pyrethroid compounds such as etofenprox, penvalerate, esfenvalerate, phenpropatrine, cypermethrin, permethrin, cyhalothrin, deltamethrin, cycloprotrin, fluvalinate, bifent Lean, tralomethrin, silafluorophene, d-phenotrine, d-alletrin, cyphenotrin, d-resmethrin, acrinatrin, cyfluthrin, tefluthrin, transfluthrin, tetrameth Lean, alletrin, praletrin, empentrin, imiprotrin and d-puramethrin; Thiadiazine derivatives such as buprofezin; Nitroimidazolidine derivatives; Neracetoxin derivatives such as cartops, thiocyclams and benzaltops; Neonicotinoid compounds such as acetamiprid, thiamethoxam and thiacloprid; Chlorinated hydrocarbons such as endosulfan, γ-BHC and DDT; Benzoylphenylurea compounds such as chlorfluazuron, teflubenzuron and flufenoxuron; Formamidine derivatives such as amitraz and chlordimeform; Thiourea derivatives such as diafenthiuron; Phenylpyrazole compounds; Methoxadiazone; Bromopropylate; Tetradipon; Chinomethionate; Propargite; Fenbutatin oxide; Hexathiax; Clofenthezin; Pyridane; Fenpyroximate; Tebufenpyrad; Polynactin complexes [tetralactin, dianthin and triactin]; Pyrimidifene; Milbemectin; Abamectin; Ivermectin and azadirachtin [AZAD].
    [47] Example
    [48] The invention will be illustrated in more detail by the preparation examples, formulation examples and test examples, but the invention is not limited to these examples.
    [49] Preparation examples are shown below.
    [50] Preparation Example 1
    [51]
    [52] 14.1 g of 4-hydroxy-6-methyl-2-pyrone was suspended in 240 ml of toluene, followed by 1.94 g of 4-dimethylaminopyridine, 16.6 g of 4,4,4-trifluorobutyric acid and dicyclohexylcarbodie. Add 21.9 g of mead. These reaction mixtures are stirred at room temperature for 1 hour and further stirred at 70 ° C. for 20 hours. After cooling to room temperature, it is filtered. The filtrate is washed twice with 1% hydrochloric acid and then once with saturated brine. The organic layer is dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography to give 5.38 g of 4-hydroxy-6-methyl-3- (4,4,4-trifluorobutyryl) -2-pyrone (hereinafter referred to as compound (A) of the present invention). To obtain.
    [53] Melting point 104 캜.
    [54] 1 H NMR (250 MHz, CDCl 3 / TMS): δ (ppm) 16.01 (s, 1H), 5.98 (s, 1H), 3.38 (t, J = 7.5 Hz, 2H), 2.62-2.42 (m, 2H) , 2.30 (s, 3 H).
    [55] Preparation Example 2
    [56]
    [57] 2.00 g of 4-hydroxy-6-methyl-2-pyrone, 240 mg of 4-dimethylaminopyridine, 2.48 g of 3-methyl-4,4,4-trifluorobutyric acid, 3.27 g of dicyclohexylcarbodiimide and 100 toluene 4-hydroxy-6-methyl-3- (3-trifluoromethylbutyryl) -2-pyrone [hereinafter referred to as compound (B) of the present invention) 0.46 in the same manner as in Preparation Example 1 from mL; g is obtained.
    [58] Melting point 69 ° C.
    [59] 1 H NMR (250 MHz, CDCl 3 / TMS): δ (ppm) 16.17 (s, 1H), 5.97 (s, 1H), 3.41 (dd, J = 18.3, 4.1 Hz, 1H), 3.18 (dd, J = 18.3, 8.6 Hz, 1H), 3.10-2.90 (m, 1H), 2.29 (s, 3H), 1.18 (d, J = 6.8 Hz, 3H).
    [60] Preparation Example 3
    [61]
    [62] 4-hydroxy-6-methyl-2-pyrone 1.58 g, 4-dimethylaminopyridine 220 mg, 3-trifluoromethyl-4,4,4-trifluorobutyric acid 2.50 g, dicyclohexylcarbodiimide 2.60 g And 4-hydroxy-6-methyl-3- (3-trifluoromethyl-4,4,4-trifluorobutyryl) -2-pyrone in the same manner as in Preparation Example 1 from 70 ml of toluene. Hereinafter, referred to as compound (C) of the present invention] 0.17 g.
    [63] Melting point 73 ° C.
    [64] 1 H NMR (300 MHz, CDCl 3 / TMS): δ (ppm) 15.48 (s, 1H), 6.01 (s, 1H), 4.15-4.00 (m, 1H), 3.60 (d, J = 5.3 Hz, 2H) , 2.32 (s, 3 H).
    [65] Formulation examples are described below. Parts indicate parts by weight.
    [66] Formulation Example 1
    [67] 10 parts of the compounds (A), (B) or (C) of the present invention, 17.5 parts of ammonium polyoxyethylenealkyl ether sulfonate and 17.5 parts of silica were mixed with 55 parts of water under wet grinding to obtain respective formulations.
    [68] Formulation Example 2
    [69] 50 parts of the compound (A), (B) or (C) of the present invention, 3 parts of calcium ligninsulfonate, 2 parts of sodium laurylsulfonate and 45 parts of synthetic hydrous silicon oxide are ground and mixed well to obtain respective wettable powders. do.
    [70] Formulation Example 3
    [71] Two parts of the compound (A), (B) or (C) of the present invention, 88 parts of kaolin clay and 10 parts of talc are well ground and mixed to obtain respective powders.
    [72] Formulation Example 4
    [73] 20 parts of the compound (A), (B) or (C) of the present invention, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 60 parts of xylene were mixed well to obtain respective emulsifiable concentrates. do.
    [74] Formulation Example 5
    [75] 2 parts of the compound (A), (B) or (C) of the present invention, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium ligninsulfonate, 30 parts of bentonite and 65 parts of kaolin clay are finely ground and mixed, kneaded with water and then granulated Drying yields each granule.
    [76] Formulation Example 6
    [77] 28.5 parts of an aqueous solution containing 20 parts of the compound (A), (B) or (C) of the present invention, 1.5 parts of sorbitan trioleate, and 2 parts of polyvinyl alcohol were mixed and ground by sand-grinder. A particle having a diameter of 3 μm or less is produced. 40 parts of an aqueous solution containing 0.05 parts of xanthan gum and 0.1 parts of aluminum magnesium silicate were added thereto and further mixed with 10 parts of propylene glycol to obtain each 20% flowable formulation.
    [78] Formulation Example 7
    [79] 0.1 parts of the compounds (A), (B) or (C) of the present invention are dissolved in 5 parts of xylene and 5 parts of trichloroethane and then mixed with 89.9 parts of deodorized kerosene to give each 0.1% oily solution.
    [80] Formulation Example 8
    [81] A solution obtained by dissolving 0.1 parts of the compounds (A), (B) or (C) of the present invention, 0.2 parts of tetramethrin and 0.1 parts of d-phenotrine together with 10 parts of trichloromethane and 59.6 parts of deodorized equivalent flow Fill the aerosol container. Subsequently, a valve was attached to this container, and 30 parts of propellant (liquefied petroleum gas) were charged into the aerosol container under pressure through the valve to obtain each oily aerosol.
    [82] Formulation Example 9
    [83] 0.2 parts of the compound (A), (B) or (C) of the present invention, 0.2 parts of d- alletrin, 0.2 parts of d-phenotrine, 5 parts of xylene, 3.4 parts of deodorized equivalent flow and Atmos 300 ( Emulsifier; trade name of Atlas Chemical Co.) and a mixture of 1 part and 50 parts of purified water in an aerosol container. This vessel is then equipped with a valve to fill 40 parts of propellant (liquefied petroleum gas) into the aerosol vessel under pressure through the valve to obtain each aqueous aerosol.
    [84] Formulation Example 10
    [85] A solution prepared by dissolving 0.3 g of the compound (A), (B) or (C) of the present invention and 0.3 g of d-allerine in 20 ml of acetone was used as a carrier for insecticidal fragrance [Tabu powder, Pyrethrum powder ( pyrethrum mac) and wood flour 4: 3: 3 mixture] and 99.4 g. After 120 ml of water is added, the mixture is sufficiently kneaded, shaped and dried to give the respective insecticidal flavor.
    [86] Formulation Example 11
    [87] 10 g of a solution is prepared by dissolving 0.4 g of the compound (A), (B) or (C) of the present invention and 0.4 g of piperonyl butoxide in acetone. Half of the obtained solution was uniformly impregnated with a substrate for insecticide mat (flat compressed fibrils consisting of a mixture of fine cotton wool and pulp: 2.5 cm x 1.5 cm x 0.3 cm). Obtain a mat.
    [88] Formulation Example 12
    [89] A solution prepared by dissolving 10 mg of the compound (A), (B) or (C) of the present invention in 0.5 ml of acetone was used as a solid feed powder for animals (solid feed powder for breeding; manufactured by Japan Kurea Co., Ltd., CE-2) Mix uniformly with 5 g. Acetone is then removed by air drying to yield each 0.5% toxic food.
    [90] Formulation Example 13
    [91] An acetone dilution solution containing the compound (A), (B) or (C) of the present invention is impregnated into the nonwoven fabric so that the concentration of the compound of the present invention is 1 g / 1 m 2, and the acetone is air-dried to prepare each acaricide sheet To obtain.
    [92] The following test examples show that the compounds of the present invention are useful as active ingredients for controlling noxious arthropods.
    [93] Test Example 1
    [94] The filter paper with a diameter of 5.5 cm is placed at the bottom of the polyethylene cup (diameter: 5.5 cm). Formulation 0.7 ml of 500 ppm aqueous dilution obtained by diluting the formulation of the test compound prepared according to Example 1 was dropped on filter paper, and 30 mg of sucrose was then scattered. Two male German cockroaches (Blattella germanica) are placed in a covered polyethylene cup. After 6 days, the mortality rate of German cockroaches is examined. As a result, the compounds (A), (B) and (C) of the present invention were found to exhibit a mortality rate of 100%.
    [95] Test Example 2
    [96] The 5.5 cm diameter filter paper is placed at the bottom of the polyethylene cup (5.5 cm diameter). Formulation 0.7 ml of 500 ppm aqueous dilution obtained by diluting the formulation of the test compound prepared according to Example 1 was dropped on filter paper, and 30 mg of sucrose was then scattered. Ten female house flies (Musca domestica) are placed in a covered cup. After 1 day, the mortality rate of the housefly is examined. As a result, the compounds (A), (B) and (C) of the present invention were found to exhibit a mortality rate of 100%.
    [97] In addition, the following examples are compounds (A) of the present invention. Is a reference compound described as compound 2 in JP-A-51-19126 It shows a better effect.
    [98] Test Example 3
    [99] Compound (A) and the reference compound of the present invention are diluted with acetone to prepare each solution (30 g / l).
    [100] Acetone solution (0.5 µl) was applied to the back of the chest of 10 female housefly (Musca domestica) using a microsyringe (active ingredient: about 15 µg per housefly), containing water and feed in a plastic cup. Neglect housefly After 24 hours, the percent mortality is checked (3 replicates). The result is as follows.
    [101] death rate(%) Compound (A) of the present invention100 Reference compound3.3
    [102] The compounds of the present invention are excellent in controlling harmful pests.
    权利要求:
    Claims (10)
    [1" claim-type="Currently amended] Pyrone compounds of formula (I).
    Formula 1

    In Formula 1 above,
    R is a trifluoromethyl group, a hydrogen atom or a methyl group.
    [2" claim-type="Currently amended] 2. The pyrone compound of claim 1, wherein R is a trifluoromethyl group.
    [3" claim-type="Currently amended] The pyron compound according to claim 1, wherein R is a hydrogen atom.
    [4" claim-type="Currently amended] 2. The pyrone compound of claim 1, wherein R is a methyl group.
    [5" claim-type="Currently amended] A pesticide composition comprising a pyrone compound of formula 1 and a carrier.
    Formula 1

    In Formula 1 above,
    R is a trifluoromethyl group, a hydrogen atom or a methyl group.
    [6" claim-type="Currently amended] The insecticide composition according to claim 5, wherein R is a trifluoromethyl group.
    [7" claim-type="Currently amended] The insecticide composition according to claim 5, wherein R is a hydrogen atom.
    [8" claim-type="Currently amended] The insecticide composition according to claim 5, wherein R is a methyl group.
    [9" claim-type="Currently amended] A method of controlling pests, comprising applying an effective amount of a pyrone compound of formula (1) to a pest or at a place where the pests reproduce.
    Formula 1

    In Formula 1 above,
    R is a trifluoromethyl group, a hydrogen atom or a methyl group.
    [10" claim-type="Currently amended] Use of a compound of formula 1 for insecticides.
    Formula 1

    In Formula 1 above,
    R is a trifluoromethyl group, a hydrogen atom or a methyl group.
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    同族专利:
    公开号 | 公开日
    JP2002363174A|2002-12-18|
    CN1390838A|2003-01-15|
    AU780731B2|2005-04-14|
    AU4244502A|2002-12-12|
    ITTO20020476D0|2002-06-07|
    CN1200936C|2005-05-11|
    BR0202092A|2003-04-22|
    US20020197294A1|2002-12-26|
    US6509299B2|2003-01-21|
    ES2200689B1|2005-05-01|
    ITTO20020476A1|2003-12-09|
    ES2200689A1|2004-03-01|
    引用文献:
    公开号 | 申请日 | 公开日 | 申请人 | 专利标题
    法律状态:
    2001-06-08|Priority to JP2001173728A
    2001-06-08|Priority to JPJP-P-2001-00173728
    2002-06-04|Application filed by 스미또모 가가꾸 고교 가부시끼가이샤
    2002-12-16|Publication of KR20020093570A
    优先权:
    申请号 | 申请日 | 专利标题
    JP2001173728A|JP2002363174A|2001-06-08|2001-06-08|Pyrone compound and its usage|
    JPJP-P-2001-00173728|2001-06-08|
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