JPH0469B2 - - Google Patents
Info
- Publication number
- JPH0469B2 JPH0469B2 JP14715683A JP14715683A JPH0469B2 JP H0469 B2 JPH0469 B2 JP H0469B2 JP 14715683 A JP14715683 A JP 14715683A JP 14715683 A JP14715683 A JP 14715683A JP H0469 B2 JPH0469 B2 JP H0469B2
- Authority
- JP
- Japan
- Prior art keywords
- parts
- compound
- present
- formulation example
- ethyl acetate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000002917 insecticide Substances 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 238000009472 formulation Methods 0.000 description 14
- -1 3-chloro-5-trifluoromethyl-2-pyridone sodium salt Chemical compound 0.000 description 13
- 239000000843 powder Substances 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000004927 clay Substances 0.000 description 5
- ABNQGNFVSFKJGI-UHFFFAOYSA-N 2,3-dichloro-5-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CN=C(Cl)C(Cl)=C1 ABNQGNFVSFKJGI-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000000443 aerosol Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 239000003350 kerosene Substances 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 239000005995 Aluminium silicate Substances 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
- 239000003915 liquefied petroleum gas Substances 0.000 description 3
- 229910052814 silicon oxide Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
- 241000238657 Blattella germanica Species 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000255925 Diptera Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-UHFFFAOYSA-N 0.000 description 2
- 241000257226 Muscidae Species 0.000 description 2
- 240000007594 Oryza sativa Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 2
- 239000000440 bentonite Substances 0.000 description 2
- 229910000278 bentonite Inorganic materials 0.000 description 2
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000002316 fumigant Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- CXBMCYHAMVGWJQ-CABCVRRESA-N (1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)methyl (1r,3r)-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCN1C(=O)C(CCCC2)=C2C1=O CXBMCYHAMVGWJQ-CABCVRRESA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- BYRJSCNPUHYZQE-UHFFFAOYSA-N 5-(trifluoromethyl)-1h-pyridin-2-one Chemical compound OC1=CC=C(C(F)(F)F)C=N1 BYRJSCNPUHYZQE-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 229910021532 Calcite Inorganic materials 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 241000256054 Culex <genus> Species 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- 241001466042 Fulgoromorpha Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 241000258937 Hemiptera Species 0.000 description 1
- 240000007049 Juglans regia Species 0.000 description 1
- 235000009496 Juglans regia Nutrition 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 241001477931 Mythimna unipuncta Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 241001556089 Nilaparvata lugens Species 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- BCKXLBQYZLBQEK-KVVVOXFISA-M Sodium oleate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC([O-])=O BCKXLBQYZLBQEK-KVVVOXFISA-M 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 230000001760 anti-analgesic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229960005286 carbaryl Drugs 0.000 description 1
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
- 235000021240 caseins Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- CAMHHLOGFDZBBG-UHFFFAOYSA-N epoxidized methyl oleate Natural products CCCCCCCCC1OC1CCCCCCCC(=O)OC CAMHHLOGFDZBBG-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- ZNOLGFHPUIJIMJ-UHFFFAOYSA-N fenitrothion Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C(C)=C1 ZNOLGFHPUIJIMJ-UHFFFAOYSA-N 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- NVVZQXQBYZPMLJ-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid Chemical compound O=C.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 NVVZQXQBYZPMLJ-UHFFFAOYSA-N 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000000077 insect repellent Substances 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- QPPQHRDVPBTVEV-UHFFFAOYSA-N isopropyl dihydrogen phosphate Chemical compound CC(C)OP(O)(O)=O QPPQHRDVPBTVEV-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 1
- 229940073769 methyl oleate Drugs 0.000 description 1
- 235000013379 molasses Nutrition 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000010665 pine oil Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- VEMKTZHHVJILDY-FIWHBWSRSA-N resmethrin Chemical compound CC1(C)[C@H](C=C(C)C)C1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-FIWHBWSRSA-N 0.000 description 1
- 229940108410 resmethrin Drugs 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229960005199 tetramethrin Drugs 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
本発明は式(I)
で示されるピリジルピリドン誘導体およびそれを
有効成分として含有する殺虫剤に関する。
これまでにピリジルピリドン誘導体の生物活性
としては抗炎症作用、鎮痛作用が知られているに
過ぎない(日本特許6803,196;6720,294;
6720,295)。
本発明者らは、新規農薬の合成研究を行なつた
結果、式(I)で表わされるピリジルピリドン誘
導体(以下本発明化合物(I)と称する。)が
1 極めて高い殺虫効力を有する。
2 殺虫剤抵抗性の害虫に対しても卓効を発揮す
る。
などの優れた性質を有することを見い出し本発明
を完成するに至つた。
本発明化合物(I)が特に有効な具体的害虫と
しては、ウンカ類などの半翅目、ヨトウ類などの
鱗翅目、アカイエカ、イエバエなどの双翅目、チ
ヤバネゴキブリなどの網翅目などが挙げられる。
本発明化合物(I)を合成する方法としては、
例えば、(1)2,3−ジクロロ−5−トリフルオロ
メチルピリジンをジメチルホルムアミド中、無水
酢酸ナトリウムと加熱する方法。
(2) 2,3−ジクロロ−5−トリフルオロメチル
ピリジンと3−クロロ−5−トリフルオロメチル
−2−ピリドンナトリウム塩とを、ジメチルホル
ムアミド中、銅触媒の存在下、加熱する方法によ
つて容易に合成することができる。以下参考例に
よつて合成例を示す。
(参考例 1)
2,3−ジクロロ−5−トリフルオロメチルピ
リジン4.0g、無水酢酸ナトリウム1.9gを、乾燥
したジメチルホルムアミド15mlに加え、140〜150
℃で8時間かきまぜた。反応液を氷水にあけ酢酸
エチルで抽出した。酢酸エチル層を食塩水で洗浄
の後、無水硫酸マグネシウムで乾燥した。酢酸エ
チルを留去した後、シリカゲルカラムクロマトグ
ラフイーに付し(展開溶媒n−ヘキサン:酢酸エ
チル=20:1)、〔1(2H),3−クロロ−5−ト
リフルオロメチル−3′−クロロ−5′−トリフルオ
ロメチル−2′−ビピリリジン〕−2−オン1.2gを
白色結晶として得た。
融点 108.5〜109.0℃
PMR(内部標準:テトラメチルシラン、δ値、溶
媒:重クロロホルム)
7.77(2H,S),8.19(1H),8.77(1H)
1R 1680cm-1(カルボニル)
元素分析
C% H% N% Cl%
実測値 38.33 1.16 7.46 18.62
(計算値 38.22 1.07 7.43 18.83)
C12 H4 Cl2 F6 N2Oとして
(参考例 2)
水素化ナトリウム100mg(62%)を、乾燥した
ジメチルホルムアミド10mlに加え、3−クロロ−
5−トリフルオロメチル−2−ピリドン500mgを
20℃で加えた。15分かきまぜた後、2,3−ジク
ロロ−5−トリフルオロメチルピリジン660mg、
塩化第一銅20mgを加え、140〜150℃で5時間かき
まぜた。氷水にあけて、酢酸エチルで抽出した。
酢酸エチル層を食塩水で洗浄の後、溶媒留去後、
シリカゲルカラムクロマトグラフイーに付し(ク
ロマト条件は参考例1と同様)、目的物を白色結
晶として350mg得た。
本発明化合物(I)を殺虫剤の有効成分として
用いる場合は、他の何らの成分も加えず、そのま
ま使用してもよいが、通常は、個体担体、液体担
体、ガス状担体、界面活性剤、その他の製剤用補
助剤等、餌等と混合し、あるいは線香やマツト等
の基材に含浸して、乳剤、水和剤、粉剤、粒剤、
油剤、エアゾール、蚊取線香や電気蚊取マツト等
の加熱燻蒸剤、フオツギング等の煙霧剤、非加熱
燻蒸剤、毒餌等に製剤する。
これらの製剤には有効成分として本発明化合物
を、重量比で0.01%〜95%含有する。固体担体と
しては、カオリンクレー、アツタパルジヤイトク
レー、ベントナイト、酸性白土、ピロフイライ
ト、タルク、珪藻土、方解石、トウモロコシ穂軸
粉、クルミ殻粉、尿素、硫酸アンモニウム、合成
含水酸化珪素等の微粉末あるいは粒状物が挙げら
れ、液体担体としては、ケロシン、灯油等の脂肪
族炭化水素、ベンゼン、トルエン、キシレン、メ
チルナフタレン等の芳香族炭化水素、ジクロロエ
タン、トリクロロエチレン、四塩化炭素等のハロ
ゲン化炭化水素、メタノール、エタノール、イソ
プロパノール、エチレングリコール、セロソルブ
等のアルコール、アセトン、メチルエチルケト
ン、シクロヘキサノン、イソホロン等のケトン、
ジエチルエーテル、ジオキサン、テトラヒドロフ
ラン等のエーテル、酢酸エチル等のエステル、ア
セトニトリル、イソブチロニトリル等のニトリ
ル、ジメチルホルムアミド、ジメチルアセトアミ
ド等の酸アミド、ジメチルスルホキシド、大豆
油、綿実油等の植物油等が挙げられる。ガス状担
体としては、フロンガス、LPG(液化石油ガス)、
ジメチルエーテル等が挙げられる。乳化、分散、
湿展等のために用いられる界面活性剤としては、
アルキル硫酸エステル塩、アルキル(アリール)
スルホン酸塩、ジアルキルスルホこはく酸塩、ポ
リオキシエチレンアルキルアリールエーテルりん
酸エステル塩、ナフタレンスルホン酸ホルマリン
縮合物等の陰イオン界面活性剤、ポリオキシエチ
レンアルキルエーテル、ポリオキシエチレンポリ
オキシプロピレンブロツクコポリマー、ソルビタ
ン脂肪酸エステル、ポリオキシエチレンソルビタ
ン脂肪酸エステル等の非イオン界面活性剤が挙げ
られる。固着剤や分散剤等の製剤用補助剤として
は、リグニンスルホン酸塩、アルギン酸塩、ポリ
ビニルアルコール、アラビアガム、糖蜜、カゼイ
ン、ゼラチン、CMC(カルボキシメチルセルロー
ス)、松根油、寒天等が挙げられ、安定剤として
は、PAP(酸性りん酸イソプロピル)、TCP(りん
酸トリクレジル)等のりん酸アルキル、植物油、
エポキシ化油、前記の界面活性剤、BHT,BHA
等の酸化防止剤、オレイン酸ナトリウム、ステア
リン酸カルシウム等の脂肪酸塩、オレイン酸メチ
ル、ステアリン酸メチル等の脂肪酸エステル等が
挙げられる。
次に製剤例を示す。
なお、以下の製剤例において、部は重量部を示
す。
製剤例 1
本発明化合物(I)0.2部、キシレン2部およ
び白灯油97.8部を混合し、油剤を得る。
製剤例 2
本発明化合物(I)10部、ポリオキシエチレン
スチリルフエニルエーテル14部、ドデシルベンゼ
ンスルホン酸カルシウム6部およびキシレン70部
をよく混合して乳剤を得る。
製剤例 3
本発明化合物(I)20部、フエニトロチオン10
部、リグニンスルホン酸カルシウム3部、ラウリ
ル硫酸ナトリウム2部および合成含水酸化珪素65
部をよく粉砕混合して水和剤を得る。
製剤例 4
本発明化合物(I)1部、カルバリール2部、
カオリンクレー87部およびタルク10部をよく粉砕
混合して粉剤を得る。
製剤例 5
本発明化合物(I)5部、合成含水酸化珪素1
部、リグニンスルホン酸カルシウム2部、ベント
ナイト30部およびカオリンクレー62部をよく粉砕
混合し、水を加えてよく練り合わせた後、造粒乾
燥して粒剤を得る。
製剤例 6
本発明化合物(I)0.05部、テトラメスリン
0.2部、レスメスリン0.05部、キシレン7部およ
び脱臭灯油32.7部を混合溶解し、エアゾール容器
に充填し、バルブ部分を取り付けた後、該バルブ
部分を通じて噴射剤(液化石油ガス)60部を加圧
充填すればエアゾールを得る。
製剤例 7
本発明化合物(I)1gに5−プロパルギルフ
ルフリル−d−シス、トランスクリサンセメー
ト0.5g、BHT0.5gを加え、適量のアセトンに溶
解し、4.0cm×4.0cm、厚さ1.2cmの多孔セラミツク
板に均一に吸着させれば、加熱燻煙剤を得る。
これらの製剤は、そのままで、あるいは水で希
釈して用いる。また、他の殺虫剤、殺ダニ剤、殺
線虫剤、殺菌剤、除草剤、植物生長調節剤、肥
料、土壌改良剤等と混合して用いることもでき
る。
本発明化合物(I)を殺虫剤として用いる場
合、その施用量は、通常10アールあたり5g〜
500gであり、乳剤、水和剤等を水で希釈して施
用する場合は、その施用濃度は10ppm〜1000ppm
であり、粉剤、粒剤、油剤、エアゾール等は、何
ら希釈することなく、製剤のままで施用する。
次に試験例を示す。なお比較対照に用いた化合
物は、第1表の化合物記号で示す。
The present invention relates to formula (I) The present invention relates to a pyridylpyridone derivative represented by the formula and an insecticide containing the same as an active ingredient. Until now, the only known biological activities of pyridylpyridone derivatives are anti-inflammatory and analgesic effects (Japanese patents 6803, 196; 6720, 294;
6720, 295). The present inventors conducted research on the synthesis of new agricultural chemicals and found that a pyridylpyridone derivative represented by formula (I) (hereinafter referred to as the compound (I) of the present invention) has extremely high insecticidal efficacy. 2. Extremely effective against insecticide-resistant pests. They discovered that it has excellent properties such as, and completed the present invention. Specific pests to which the compound (I) of the present invention is particularly effective include Hemiptera such as planthoppers, Lepidoptera such as armyworms, Diptera such as Culex mosquitoes and houseflies, and Reciptera such as the German cockroach. Can be mentioned. The method for synthesizing the compound (I) of the present invention is as follows:
For example, (1) a method in which 2,3-dichloro-5-trifluoromethylpyridine is heated with anhydrous sodium acetate in dimethylformamide. (2) By heating 2,3-dichloro-5-trifluoromethylpyridine and 3-chloro-5-trifluoromethyl-2-pyridone sodium salt in dimethylformamide in the presence of a copper catalyst. Can be easily synthesized. Synthesis examples will be shown below using reference examples. (Reference Example 1) Add 4.0 g of 2,3-dichloro-5-trifluoromethylpyridine and 1.9 g of anhydrous sodium acetate to 15 ml of dry dimethylformamide,
Stir at ℃ for 8 hours. The reaction solution was poured into ice water and extracted with ethyl acetate. The ethyl acetate layer was washed with brine and then dried over anhydrous magnesium sulfate. After distilling off the ethyl acetate, it was subjected to silica gel column chromatography (developing solvent: n-hexane:ethyl acetate = 20:1), and [1(2H),3-chloro-5-trifluoromethyl-3'- 1.2 g of chloro-5'-trifluoromethyl-2'-bipyrylidin]-2-one was obtained as white crystals. Melting point 108.5-109.0℃ PMR (internal standard: tetramethylsilane, δ value, solvent: deuterium chloroform) 7.77 (2H, S), 8.19 (1H), 8.77 (1H) 1R 1680cm -1 (carbonyl) Elemental analysis C% H % N% Cl% Actual value 38.33 1.16 7.46 18.62 (Calculated value 38.22 1.07 7.43 18.83) As C 12 H 4 Cl 2 F 6 N 2 O (Reference example 2) 100 mg (62%) of sodium hydride was dissolved in dried dimethylformamide 10ml plus 3-chloro-
500mg of 5-trifluoromethyl-2-pyridone
Added at 20°C. After stirring for 15 minutes, 660 mg of 2,3-dichloro-5-trifluoromethylpyridine,
20 mg of cuprous chloride was added and stirred at 140-150°C for 5 hours. It was poured into ice water and extracted with ethyl acetate.
After washing the ethyl acetate layer with brine and evaporating the solvent,
The product was subjected to silica gel column chromatography (chromatography conditions were the same as in Reference Example 1) to obtain 350 mg of the desired product as white crystals. When the compound (I) of the present invention is used as an active ingredient of an insecticide, it may be used as it is without adding any other ingredients, but it is usually used in combination with a solid carrier, liquid carrier, gaseous carrier, or surfactant. , other formulation auxiliaries, etc., mixed with feed, etc., or impregnated into base materials such as incense sticks and mats, to produce emulsions, wettable powders, powders, granules, etc.
It is formulated into oil solutions, aerosols, heating fumigants such as mosquito coils and electric mosquito repellents, fogging agents such as fogging, non-heating fumigants, poison baits, etc. These preparations contain 0.01% to 95% by weight of the compound of the present invention as an active ingredient. Examples of solid carriers include fine powders or granules such as kaolin clay, attapalgite clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, corn cob powder, walnut shell powder, urea, ammonium sulfate, and synthetic hydrous silicon oxide. Liquid carriers include aliphatic hydrocarbons such as kerosene and kerosene, aromatic hydrocarbons such as benzene, toluene, xylene, and methylnaphthalene, halogenated hydrocarbons such as dichloroethane, trichloroethylene, and carbon tetrachloride, and methanol. , alcohols such as ethanol, isopropanol, ethylene glycol, and cellosolve; ketones such as acetone, methyl ethyl ketone, cyclohexanone, and isophorone;
Examples include ethers such as diethyl ether, dioxane, and tetrahydrofuran, esters such as ethyl acetate, nitriles such as acetonitrile and isobutyronitrile, acid amides such as dimethylformamide and dimethylacetamide, and vegetable oils such as dimethyl sulfoxide, soybean oil, and cottonseed oil. . Gaseous carriers include fluorocarbon gas, LPG (liquefied petroleum gas),
Examples include dimethyl ether. emulsification, dispersion,
Surfactants used for wet spreading, etc.
Alkyl sulfate salt, alkyl (aryl)
Anionic surfactants such as sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkylaryl ether phosphate ester salts, naphthalene sulfonic acid formalin condensates, polyoxyethylene alkyl ethers, polyoxyethylene polyoxypropylene block copolymers, Examples include nonionic surfactants such as sorbitan fatty acid ester and polyoxyethylene sorbitan fatty acid ester. Formulation aids such as fixing agents and dispersants include lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, molasses, casein, gelatin, CMC (carboxymethyl cellulose), pine oil, agar, etc., and are stable. Agents include alkyl phosphates such as PAP (isopropyl acid phosphate) and TCP (tricresyl phosphate), vegetable oil,
Epoxidized oil, surfactants mentioned above, BHT, BHA
, fatty acid salts such as sodium oleate and calcium stearate, and fatty acid esters such as methyl oleate and methyl stearate. Examples of formulations are shown below. In addition, in the following formulation examples, parts indicate parts by weight. Formulation Example 1 0.2 parts of the compound (I) of the present invention, 2 parts of xylene and 97.8 parts of white kerosene are mixed to obtain an oil solution. Formulation Example 2 10 parts of the compound (I) of the present invention, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 70 parts of xylene are thoroughly mixed to obtain an emulsion. Formulation Example 3 20 parts of the compound (I) of the present invention, 10 parts of fenitrothion
3 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and 65 parts of synthetic hydrated silicon oxide.
Thoroughly grind and mix the two parts to obtain a wettable powder. Formulation Example 4 1 part of the compound (I) of the present invention, 2 parts of carbaryl,
87 parts of kaolin clay and 10 parts of talc are thoroughly ground and mixed to obtain a powder. Formulation Example 5 5 parts of the compound (I) of the present invention, 1 part of synthetic hydrated silicon oxide
1 part, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 62 parts of kaolin clay are thoroughly ground and mixed, water is added and the mixture is thoroughly kneaded, followed by granulation and drying to obtain granules. Formulation Example 6 0.05 part of the compound (I) of the present invention, tetramethrin
Mix and dissolve 0.2 parts of Resmethrin, 0.05 parts of xylene, and 32.7 parts of deodorized kerosene, fill it into an aerosol container, attach the valve part, and then pressurize and fill 60 parts of propellant (liquefied petroleum gas) through the valve part. Then you get an aerosol. Formulation Example 7 Add 5-propargylfurfuryl-d-cis, 0.5 g of transchrysansemate, and 0.5 g of BHT to 1 g of the compound (I) of the present invention, dissolve in an appropriate amount of acetone, and prepare a 4.0 cm x 4.0 cm, thickness 1.2 If it is evenly adsorbed onto a cm porous ceramic plate, a hot smoking agent will be obtained. These preparations can be used as is or diluted with water. It can also be used in combination with other insecticides, acaricides, nematicides, fungicides, herbicides, plant growth regulators, fertilizers, soil conditioners, etc. When the compound (I) of the present invention is used as an insecticide, the application amount is usually 5 g to 10 are.
500g, and when applying emulsions, wettable powders, etc. diluted with water, the application concentration is 10ppm to 1000ppm.
Powders, granules, oils, aerosols, etc. are applied as they are without any dilution. Next, a test example is shown. The compounds used for comparison are indicated by the compound symbols in Table 1.
【表】
試験例 1
直径5.5cmのポリエチレンカツプの底に同大の
紙をしき、製剤例2によつて得られた本発明化
合物(I)および対照化合物の乳剤の水による所
定濃度希釈液0.7mlを紙上に滴下した。餌とし
て、シユークロース30mgを紙上に入れた。その
中に殺虫剤抵抗性系統イエバエ雌成虫を各々10頭
放ち、フタをして48時間後に生死を調査し、死虫
率を求めた(2反復)。
結果を下表に示す。[Table] Test Example 1 Place paper of the same size on the bottom of a polyethylene cup with a diameter of 5.5 cm, and dilute the emulsion of the compound (I) of the present invention and the control compound obtained in Formulation Example 2 with water to a predetermined concentration of 0.7. ml was dropped onto the paper. As bait, 30 mg of sucrose was placed on the paper. Ten female adult house flies of the insecticide-resistant strain were released into each container, the lids were closed, and 48 hours later, the survival rate was determined to determine the mortality rate (2 repetitions). The results are shown in the table below.
【表】
試験例 2
製剤例2によつて得られた本発明化合物(I)
および対照化合物の乳剤の水による所定濃度の希
釈液にイネ茎(長さ12cm)を1分間浸漬した。風
乾後、試験管にイネ茎を入れ、ヒメトビウンカ成
虫を10頭放ち、1日後に生死を調査し、LC50値
(50%致死濃度)を求めた(2反復)。
結果を下表に示す。[Table] Test Example 2 Compound (I) of the present invention obtained by Formulation Example 2
Rice stems (12 cm in length) were immersed for 1 minute in a diluted emulsion of the control compound and a control compound with water at a predetermined concentration. After air-drying, the rice stems were placed in a test tube, 10 adult brown planthoppers were released, and one day later, they were examined to see if they were alive or dead, and the LC50 value (50% lethal concentration) was determined (2 repetitions). The results are shown in the table below.
【表】
試験例 3
直径5.5cmのポリエチレンカツプの底に同大の
紙をしき、製剤例2によつて得られた本発明化
合物(I)および対照化合物の乳剤の水による所
定濃度希釈液0.7mlを紙上に滴下した。餌とし
てシユークロース30mgを紙上に入れた。その中
にチヤバネゴキブリ雄成虫を10頭放ち、フタをし
て48時間後に生死を調査し、死虫率を求めた(2
反復)。
結果を下表に示す。[Table] Test Example 3 A piece of paper of the same size was placed at the bottom of a polyethylene cup with a diameter of 5.5 cm, and the emulsion of the compound (I) of the present invention and the control compound obtained in Formulation Example 2 was diluted with water at a predetermined concentration of 0.7. ml was dropped onto the paper. As bait, 30 mg of sucrose was placed on the paper. We released 10 male German cockroaches into the container, covered it, and examined whether it was alive or dead after 48 hours to determine the mortality rate (2
repetition). The results are shown in the table below.
Claims (1)
して含有することを特徴とする殺虫剤。[Claims] 1 formula A pyridylpyridone derivative represented by 2 formulas An insecticide characterized by containing a pyridylpyridone derivative represented by the following as an active ingredient.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP14715683A JPS6038363A (en) | 1983-08-10 | 1983-08-10 | Pyridylpypyridone derivative and insecticide containing it as active ingredient |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP14715683A JPS6038363A (en) | 1983-08-10 | 1983-08-10 | Pyridylpypyridone derivative and insecticide containing it as active ingredient |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS6038363A JPS6038363A (en) | 1985-02-27 |
JPH0469B2 true JPH0469B2 (en) | 1992-01-06 |
Family
ID=15423848
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP14715683A Granted JPS6038363A (en) | 1983-08-10 | 1983-08-10 | Pyridylpypyridone derivative and insecticide containing it as active ingredient |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS6038363A (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6172754A (en) * | 1984-09-18 | 1986-04-14 | Sumitomo Chem Co Ltd | Pyridylpyridone derivative and insecticide containing it as active ingredient |
BRPI0715137B8 (en) * | 2006-08-10 | 2021-10-19 | Nippon Soda Co | Agrochemical composition containing an agrochemically active ingredient having a restricted wetting capacity |
-
1983
- 1983-08-10 JP JP14715683A patent/JPS6038363A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS6038363A (en) | 1985-02-27 |
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