JPH043382B2 - - Google Patents
Info
- Publication number
- JPH043382B2 JPH043382B2 JP16574983A JP16574983A JPH043382B2 JP H043382 B2 JPH043382 B2 JP H043382B2 JP 16574983 A JP16574983 A JP 16574983A JP 16574983 A JP16574983 A JP 16574983A JP H043382 B2 JPH043382 B2 JP H043382B2
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- formula
- compound
- compound represented
- reaction
- 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
- 150000001875 compounds Chemical class 0.000 claims description 37
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 10
- 239000002917 insecticide Substances 0.000 claims description 7
- 239000011230 binding agent Substances 0.000 claims description 6
- 150000002923 oximes Chemical class 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000005905 mesyloxy group Chemical group 0.000 claims description 2
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- -1 hemiketals Chemical class 0.000 description 12
- 238000009472 formulation Methods 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 241000607479 Yersinia pestis Species 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 241000238631 Hexapoda Species 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 230000003054 hormonal effect Effects 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance 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
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000256054 Culex <genus> Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- 241000257226 Muscidae Species 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- OUNSASXJZHBGAI-UHFFFAOYSA-N Salithion Chemical compound C1=CC=C2OP(OC)(=S)OCC2=C1 OUNSASXJZHBGAI-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-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
- 150000008055 alkyl aryl sulfonates Chemical class 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
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000073 carbamate insecticide Substances 0.000 description 2
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 2
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- DIRFUJHNVNOBMY-UHFFFAOYSA-N fenobucarb Chemical compound CCC(C)C1=CC=CC=C1OC(=O)NC DIRFUJHNVNOBMY-UHFFFAOYSA-N 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 230000000366 juvenile effect Effects 0.000 description 2
- 239000003350 kerosene Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- VOEYXMAFNDNNED-UHFFFAOYSA-N metolcarb Chemical compound CNC(=O)OC1=CC=CC(C)=C1 VOEYXMAFNDNNED-UHFFFAOYSA-N 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 2
- KEUPLGRNURQXAR-UHFFFAOYSA-N (4-chlorophenyl) acetate Chemical compound CC(=O)OC1=CC=C(Cl)C=C1 KEUPLGRNURQXAR-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241001414720 Cicadellidae Species 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- 241001587415 Cryptoblabes gnidiella Species 0.000 description 1
- 239000005947 Dimethoate Substances 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- KKUKTXOBAWVSHC-UHFFFAOYSA-N Dimethylphosphate Chemical compound COP(O)(=O)OC KKUKTXOBAWVSHC-UHFFFAOYSA-N 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- 241001466042 Fulgoromorpha Species 0.000 description 1
- 241000255896 Galleria mellonella 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
- 241000255777 Lepidoptera Species 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical compound CON GMPKIPWJBDOURN-UHFFFAOYSA-N 0.000 description 1
- 241000257159 Musca domestica 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
- 241000238814 Orthoptera Species 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 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
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 210000001142 back Anatomy 0.000 description 1
- 235000012216 bentonite Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229960005286 carbaryl Drugs 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 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
- 229920006184 cellulose methylcellulose Polymers 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- OEBRKCOSUFCWJD-UHFFFAOYSA-N dichlorvos Chemical compound COP(=O)(OC)OC=C(Cl)Cl OEBRKCOSUFCWJD-UHFFFAOYSA-N 0.000 description 1
- 229950001327 dichlorvos Drugs 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- YLFBFPXKTIQSSY-UHFFFAOYSA-N dimethoxy(oxo)phosphanium Chemical compound CO[P+](=O)OC YLFBFPXKTIQSSY-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 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
- 239000000417 fungicide Substances 0.000 description 1
- 239000003502 gasoline 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
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000002373 hemiacetals Chemical class 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 230000000887 hydrating effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-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
- 229930014550 juvenile hormone Natural products 0.000 description 1
- 239000002949 juvenile hormone Substances 0.000 description 1
- 150000003633 juvenile hormone derivatives Chemical class 0.000 description 1
- 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 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000011707 mineral Substances 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
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000003992 organochlorine insecticide Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 229960000490 permethrin Drugs 0.000 description 1
- RLLPVAHGXHCWKJ-UHFFFAOYSA-N permethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 RLLPVAHGXHCWKJ-UHFFFAOYSA-N 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 229920013635 phenyl ether polymer Polymers 0.000 description 1
- 239000010665 pine oil Substances 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 230000019617 pupation Effects 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 150000005846 sugar alcohols Chemical class 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
- 210000000115 thoracic cavity Anatomy 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 239000010981 turquoise Substances 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 235000015099 wheat brans Nutrition 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
本発明は、一般式（）
〔式中、R1は水素原子またはメチル基を表わ
し、R2は炭素原子数１〜３のアルキル基を表わ
し、ｍは１〜３の整数を表わし、ｎは０または１
を表わす。〕
で示されるオキシム誘導体（以下、本発明化合物
と称する。）、その製造法およびそれを有効成分と
して含有する殺虫剤に関するものである。
有機リン系殺虫剤や有機塩素系殺虫剤あるいは
カーバメート系殺虫剤が害虫防除にはたしてきた
役割は非常に大きいものであるが、これらのある
物は毒性が高く、また残留性により生態系を乱す
ためきわめて憂慮すべき状況となつている。ま
た、近年ある種の害虫、たとえばイエバエ、ウン
カ類、ヨコバイ類、メイ虫類等に殺虫剤抵抗性が
問題となつている。
本発明はかかる状況に対処すべく、低濃度でき
わめて優れた防除効果を示す幼若ホルモン様活性
を有する化合物を用いて農林園芸害虫、貯穀害虫
および衛生害虫等の防除を目的とするものであ
る。
本発明者らは鋭意研究を行なつた結果、一般式
（）で示される化合物が幼若ホルモン活性を有
し、鞘翅目、鱗翅目、半翅目、直翅目、双翅目等
の昆虫にきわめて高い防除効果を示すことを見出
した。
一般式（）で示される本発明化合物は、次の
方法により製造することができる。
（製造法Ａ）
一般式（）
〔式中、R1，ｍおよびｎは前述と同じ意味を
表わす。〕
で示される化合物または該反応性誘導体と一般式
（）
R2−Ｏ−NH2 （）
〔式中、R2は前述と同じ意味を表わす。〕
で示される化合物または該反応性誘導体とを反応
させる。
ここに、一般式（）で示される化合物は、そ
の反応性誘導体として、アセタール、ケタール、
ヘミアセタール、ヘミケタール、水和物等のすべ
てを包含してなり、反応系内で一般式（）を形
成し得るすべての一般式（）の誘導体を含む。
また、一般式（）で示される化合物は、その
反応性誘導体として、塩酸塩、硫酸塩等の鉱酸塩
類、有機酸塩類、本発明化合物に含まれるオキシ
ムエーテル類およびその他のオキシムエーテル類
等を包含してなり、反応系内で一般式（）を形
成し得るすべての一般式（）の誘導体を含む。
本反応は、不活性溶媒の存在下または不存在
下、いずれの場合でもよく、酸またはアルカリの
存在下または不存在下のいずれでもよい。
好適な溶媒としては、水、ベンゼン、トルエ
ン、ピリジン、四塩化炭素、クロロホルム、エチ
レンクロリド、塩化メチレン等およびこれらの２
種以上の混合溶媒があげられる。好適な酸は、塩
酸、硫酸、ｐ−トルエンスルホン酸が、好適なア
ルカリは、水酸化ナトリウム、水酸化カリウム、
炭酸カリウム等の無機塩基またはトリエチルアミ
ン、ピリジン等の有機塩基である。
反応温度は特に制限されないが、一般に30℃な
いし反応混合物の沸点の温度、好ましくは室温な
いし100℃の温度である。一般に反応は、0.5〜24
時間で完予する。
一般式（）で示される化合物と一般式（）
で示される化合物とのモル比は、普通１：１〜20
であり、好ましくは１：1.1〜1.2である。
（製造法Ｂ）
一般式（）
〔式中、R1.mおよびｎは前述と同じ意味を表
わす。〕
で示される化合物と一般式（）
R2−Ｘ （）
〔式中、R2は前述と同じ意味を表わし、Ｘは
ハロゲン原子、メシルオキシ基またはトシルオキ
シ基を表わす。〕
で示される化合物とを酸結合剤の存在下に反応さ
せる。
本反応において、酸結合剤としては、たとえば
アルカリ金属、アルカリ金属水素化物、アルカリ
金属アミド、アルカリ金属水酸化物、アルカリ金
属炭酸塩およびトリエチルアミン、トリメチルア
ミン、ピリジン等の有機塩基等があげられる。
このような酸結合剤は、そのまま他の反応試剤
と共に反応系に加えてもよいが、アルカリ金属由
来の上記の酸結合剤を使用する場合には、予め酸
結合剤と一般式（）で示される化合物とを反応
させ、一般式（′）
〔式中、Ｑはアルカリ金属原子を表わす。〕
で示されるアルコラートを形成させておいて、こ
れに一般式（）で示される化合物を反応させる
こともできる。
本反応は、不活性有機溶媒中で行なうのが都合
がよく、好適な溶媒としては、ジメチルホルムア
ミド、ジメチルスルホキシド、テトラヒドロフラ
ン、ジメトキシエタン、トルエン、水等およびこ
れらの２種以上の混合溶媒があげられる。反応溶
媒として、水または水と他の有機溶媒との混合溶
媒を用いる場合には、ベンジルトリエチルアンモ
ニウムクロリドおよびテトラｎ−ブチルアンモニ
ウムブロミド等の相関移動触媒を用いることによ
り、効率よく反応が進行する。
反応温度は特に制限されるものではないが、一
般に−30℃ないし反応混合物の沸点の温度、好ま
しくは室温ないし100℃の温度である。一般に反
応は、0.5〜24時間で完了する。
一般式（）または（′）で示される化合物
と一般式（）で示される化合物とのモル比は、
普通１：１〜３であり、好ましくは１：1.1〜1.2
である。
得られた本発明化合物は必要に応じてカラムク
ロマトグラフイー、蒸留等の手段により精製する
ことができる。
なお、本発明化合物にはオキシムに由来する幾
何異性体が存在するが、これらも本発明に含まれ
ることは言うまでもない。
次に製造例を示す。
製造例 １
（製造法Ａ）による化合物(5)の製造
４−（４−フエノキシ）ブチルアルデヒド1.50
ｇ（5.85mmol）をジメチルホルムアミド20mlに
溶解し、氷冷下に撹拌しながらＯ−メチルヒドロ
キシルアミン．塩酸塩1.00ｇ（11.2mmol）を30
分間を要して添加した。完了後室温で１晩撹拌し
た後、反応液を水に投じてトルエンで抽出した。
抽出液を十分に水洗した後、濃縮し、残渣を塩化
メチレンを展開溶媒としたシリカゲルカラムクロ
マトグラフイーで精製することにより、1.22ｇの
目的とする化合物(5)を無色油状物として得た（収
率73.1％、n24.5 D1.5563）。
製造例 ２
（製造法Ｂ）による化合物(1)の製造
３−（４−フエノキシフエノキシ）プロピオン
アルドオキシム1.50ｇ（5.83mmol）をジメチル
ホルムアミド20mlに溶解し、氷冷下内温10℃以下
で撹拌しながらNaH（純度62.1％）0.23ｇ
（5.83mmol）を添加した。完了後２時間撹拌を続
行した後、ヨウ化エチル1.09ｇ（7.11mmol）を
適下した。滴下完了後、室温にて１晩撹拌した
後、反応液を水に投じてトルエンで抽出した。抽
出液を水洗後、濃縮し、残渣を塩化メチレンを展
開溶媒としたシリカゲルカラムクロマトグラフイ
ーで精製することにより、1.07ｇの目的とする化
合物(1)を無色油状物として得た（収率64.3％、
n23.0 D1.5571）。次にこれらの製造例に示した製造
法に準じて製造した本発明化合物のいくつかを表
１に示す。
The present invention is based on the general formula () [In the formula, R 1 represents a hydrogen atom or a methyl group, R 2 represents an alkyl group having 1 to 3 carbon atoms, m represents an integer of 1 to 3, and n represents 0 or 1.
represents. ] The present invention relates to an oxime derivative represented by (hereinafter referred to as the compound of the present invention), a method for producing the same, and an insecticide containing the same as an active ingredient. Organophosphorus insecticides, organochlorine insecticides, and carbamate insecticides have played a very important role in pest control, but some of these substances are highly toxic and disturb the ecosystem due to their persistence. The situation is extremely worrying. Furthermore, in recent years, resistance to insecticides has become a problem in certain pest insects, such as houseflies, planthoppers, leafhoppers, and insects. In order to cope with such a situation, the present invention aims to control agricultural, forestry, and horticultural pests, grain storage pests, sanitary pests, etc. using a compound having juvenile hormone-like activity that exhibits extremely excellent control effects at low concentrations. . As a result of intensive research, the present inventors have found that the compound represented by the general formula () has juvenile hormone activity, and has been found to be effective against insects such as Coleoptera, Lepidoptera, Hemiptera, Orthoptera, and Diptera. It was found that it has an extremely high pesticidal effect. The compound of the present invention represented by the general formula () can be produced by the following method. (Manufacturing method A) General formula () [In the formula, R 1 , m and n have the same meanings as above. ] A compound or the reactive derivative represented by the general formula () R 2 -O-NH 2 () [wherein R 2 represents the same meaning as above. ] A compound represented by these or the reactive derivative thereof is reacted. Here, the compound represented by the general formula () includes acetal, ketal,
It includes all hemiacetals, hemiketals, hydrates, etc., and includes all derivatives of general formula () that can form general formula () within the reaction system. In addition, the compound represented by the general formula () includes mineral acid salts such as hydrochloride and sulfate, organic acid salts, oxime ethers and other oxime ethers contained in the compounds of the present invention as reactive derivatives thereof. It includes all derivatives of the general formula () that can form the general formula () in the reaction system. This reaction may be carried out in the presence or absence of an inert solvent, and may be carried out in the presence or absence of an acid or alkali. Suitable solvents include water, benzene, toluene, pyridine, carbon tetrachloride, chloroform, ethylene chloride, methylene chloride, etc.
Examples include mixed solvents of more than one species. Suitable acids are hydrochloric acid, sulfuric acid, p-toluenesulfonic acid, and suitable alkalis include sodium hydroxide, potassium hydroxide,
Inorganic bases such as potassium carbonate or organic bases such as triethylamine and pyridine. The reaction temperature is not particularly limited, but is generally from 30°C to the boiling point of the reaction mixture, preferably from room temperature to 100°C. Generally the reaction is between 0.5 and 24
Complete in time. Compounds represented by general formula () and general formula ()
The molar ratio with the compound represented by is usually 1:1 to 20
and preferably 1:1.1-1.2. (Manufacturing method B) General formula () [In the formula, R 1 .m and n represent the same meanings as above. ] A compound represented by the general formula () R 2 -X () [wherein R 2 represents the same meaning as above, and X represents a halogen atom, mesyloxy group or tosyloxy group. ] is reacted with the compound shown in the following in the presence of an acid binder. In this reaction, examples of the acid binder include alkali metals, alkali metal hydrides, alkali metal amides, alkali metal hydroxides, alkali metal carbonates, and organic bases such as triethylamine, trimethylamine, and pyridine. Such an acid binder may be added as is to the reaction system along with other reaction reagents, but when using the above acid binder derived from an alkali metal, the acid binder and the general formula () shown in The general formula (′) is [In the formula, Q represents an alkali metal atom. ] It is also possible to form an alcoholate represented by the following and then react it with a compound represented by the general formula (). This reaction is conveniently carried out in an inert organic solvent, and suitable solvents include dimethylformamide, dimethyl sulfoxide, tetrahydrofuran, dimethoxyethane, toluene, water, etc., and mixed solvents of two or more of these. . When water or a mixed solvent of water and another organic solvent is used as the reaction solvent, the reaction proceeds efficiently by using a phase transfer catalyst such as benzyltriethylammonium chloride and tetra n-butylammonium bromide. The reaction temperature is not particularly limited, but generally ranges from -30°C to the boiling point of the reaction mixture, preferably from room temperature to 100°C. Generally the reaction is complete in 0.5 to 24 hours. The molar ratio of the compound represented by the general formula () or (′) and the compound represented by the general formula () is:
Usually 1:1-3, preferably 1:1.1-1.2
It is. The obtained compound of the present invention can be purified by means such as column chromatography and distillation, if necessary. Note that the compounds of the present invention include geometric isomers derived from oximes, and it goes without saying that these are also included in the present invention. Next, a manufacturing example will be shown. Production example 1 Production of compound (5) by (Production method A) 4-(4-phenoxy)butyraldehyde 1.50
(5.85 mmol) was dissolved in 20 ml of dimethylformamide, and O-methylhydroxylamine was added while stirring under ice cooling. Hydrochloride 1.00g (11.2mmol) 30
It took a few minutes to add. After completion of stirring at room temperature overnight, the reaction solution was poured into water and extracted with toluene.
After thoroughly washing the extract with water, it was concentrated, and the residue was purified by silica gel column chromatography using methylene chloride as a developing solvent to obtain 1.22 g of the target compound (5) as a colorless oil ( Yield 73.1%, n 24.5 D 1.5563). Production Example 2 Production of Compound (1) by (Production Method B) 1.50 g (5.83 mmol) of 3-(4-phenoxyphenoxy)propionaldoxime was dissolved in 20 ml of dimethylformamide, and the temperature was adjusted to 10°C under ice cooling. 0.23 g of NaH (purity 62.1%) while stirring
(5.83 mmol) was added. After the mixture was stirred for 2 hours, 1.09 g (7.11 mmol) of ethyl iodide was added dropwise. After completion of the dropwise addition, the mixture was stirred at room temperature overnight, and then the reaction solution was poured into water and extracted with toluene. The extract was washed with water, concentrated, and the residue was purified by silica gel column chromatography using methylene chloride as a developing solvent to obtain 1.07 g of the target compound (1) as a colorless oil (yield: 64.3). %,
n 23.0 D 1.5571). Next, Table 1 shows some of the compounds of the present invention produced according to the production methods shown in these production examples.
【表】
本発明化合物は、固体担体、液体担体、界面活
性剤、その他の製剤用副資剤と混じて製剤、たと
えば乳剤、粉剤、粒剤、水和剤、微粒剤などに調
整し、各種の用途に供しうる。各製剤中には有効
成分として本発明化合物を重量比で0.1〜99.9％、
好ましくは２〜80％含有することができる。
これらの製剤は常法に従つて調整することがで
きる。この場合固体担体としては、粘土類（たと
えばカオリン、ベントナイト、酸性白土、ピロフ
イライト、セリサイト）、タルク類、その他無機
鉱物（たとえば水和二酸化ケイ素、軽石、珪藻
土、硫黄粉末、活性炭）などの微粉末ないし粉状
物があげられる。
液体担体としては、アルコール類（たとえばメ
チルアルコール、エチルアルコール）、ケトン類
（たとえばアセトン、メチルエチルケトン）、エー
テル類（たとえばエチルエーテル、ジオキサン、
セロソルブ、テトラハイドロフラン）、芳香族炭
化水素類（たとえばベンゼン、トルエン、キシレ
ン、メチルナフタレン）、脂肪族炭化水素類（た
とえばガソリン、ケロシン、灯油）、エステル類、
ニトリル類、酸アミド類（たとえばメチルホルム
アミド、ジメチルアセタマイド）、ハロゲン化炭
化水素類（たとえばジクロロエタン、トリクロロ
エチレン、四塩化炭素）などがあげられる。次に
界面活性剤としては、アルキル硫酸エステル類、
アルキルスルホン酸塩、アルキルアリールスルホ
ン酸塩、ポリエチレングリコールエーテル類、多
価アルコールエステル類などがあげられる。ま
た、使用できる固着剤や分散剤としては、カゼイ
ン、ゼラチン、でんぶん粉、CMC、アラビヤゴ
ム、アルギン酸、リグニンスルフオネート、ベン
トナイト、糖蜜、ポリビニルアルコール、松根
油、寒天などがあり、安定剤としては、たとえば
PAP（リン酸イソプロピル）、TCP（トリクレジル
ホスフエート）、トール油、エポキシ化油、各種
界面活性剤、各種脂肪酸またはそのエステルなど
があげられる。
また、これらの化合物はフエニトロチオン
｛Ｏ，Ｏ−ジメチル−Ｏ−（３−メチル−４−ニト
ロフエニレ）ホスホロチオエート｝、マラソン
〔Ｓ−｛１，２−ビス（エトキシカルボニル）エチ
ル｝Ｏ，Ｏ−ジメチルホスホロチオエート〕、ジ
メトエート｛Ｏ，Ｏ−ジメチルＳ−（Ｎ−メチル
カルバモイルメチル）ホスホロジチオエート｝、
サリチオン（２−メトキシ−4H−１，３，２−
ベンゾジオキサホスホリン−２−スルフイド）、
ダイアジノン｛Ｏ，Ｏ−ジエチルＯ−（２−イソ
プロピル−６−メチル−４−ピリミジニル）ホス
ホロチオエート｝、ジプテレツクス｛２，２，２
−トリクロロ−１−ハロドロキシエチル）Ｏ，Ｏ
−ジメチルホスホネート｝、ジクロルボス｛Ｏ−
（２，２−ジクロロビニル）Ｏ，Ｏ−ジメチルホ
スフエート｝等の有機リン系殺虫剤、MPMC
（３，４−ジメチルフエニルＮ−メチルカーバメ
ート）、MTMC（ｍ−トリルＮ−メチルカーバメ
ート）、BPMC（２−sec−ブチルフエニルＮ−メ
チルカーバメート）、カルバリル（１−ナフチル
Ｎ−メチルカーバメート）等のカーバメート系殺
虫剤、パーメスリン｛３−フエノキシベンジル
ｄ，ｌ−シス，トランス−３−（２，２−ジクロ
ロビニル）−２，２−ジメチルシクロプロパンカ
ルボキシレート｝、フエンパレレート（α−シア
ノ−ｍ−フエノキシベンジルα−イソプロピル−
ｐ−クロロフエニルアセテート）等のピレスロイ
ド系殺虫剤、殺ダニ剤、殺線虫剤、殺菌剤、除草
剤、植物生長調整剤、肥料、土壌改良剤などと任
意の割合で混合することができ、特に殺虫剤と混
合する場合には、それぞれの効力の安定と共力作
用が期待できる。
次にいくつかの製剤例および試験例を示すが本
発明はもちろんこれらのみに限定されるものでは
ない。
製剤例 １
本発明化合物(1)〜(6)の各々20部、それらに各々
乳化剤（ポリオキシエチレンスチレン化フエニル
エーテル、ポリオキシエチレンスチレン化フエニ
ルエーテルのポリマー、アルキルアリールスルホ
ン酸塩の混合物）20部、キシレン60部を加え、こ
れらをよく撹拌混合すれば、各々の乳剤を得る。
製剤例 ２
本発明化合物(1)〜(6)の各々20部に乳化剤（ラウ
リル硫酸ナトリウム）５部をよく混合し、300メ
ツシユ珪藻土75部を加え、擂潰器中にて充分撹拌
混合すれば、各々の水和剤を得る。
製剤例 ３
本発明化合物(1)〜(6)の各々３部をアセトン20部
に溶解し、300メツシユタルク97部を加え、擂潰
器中にて充分撹拌混合した後、アセトンを蒸発除
去すれば、各々の粉剤を得る。
試験例 １
本発明化合物の幼若ホルモン様活性をハチミツ
ガ蛹を用いて検討した。方法はシユナイダーマン
（J.Insect Physiol.，1965.Vol.11，1641）によつ
て報告されているものにしたがつた。すなわち、
ハチミツガ（Galleriamellonella）の蛹を蛹化20
時間内に集め、その胸背の右側に約１m2の穴をあ
け、パラフイン、ピーナツツオイルの混合物に溶
かした所定の薬量の化合物でシールした。処理蛹
は28℃の恒温器に入れ、羽化直前に処理部分のク
チクラをはぎ、蛹クチクラのできかたによつて平
均反応率を求め、変態を50％抑制するのに要する
薬量（ID50）を求めた。結果は表２に示すとおり
である。[Table] The compound of the present invention can be mixed with solid carriers, liquid carriers, surfactants, and other auxiliary ingredients for formulations to prepare formulations, such as emulsions, powders, granules, wettable powders, fine granules, etc. It can be used for various purposes. Each formulation contains the compound of the present invention as an active ingredient in a weight ratio of 0.1 to 99.9%.
Preferably, it can be contained in an amount of 2 to 80%. These formulations can be prepared according to conventional methods. In this case, solid carriers include fine powders such as clays (e.g. kaolin, bentonite, acid clay, pyrophyllite, sericite), talcs, and other inorganic minerals (e.g. hydrated silicon dioxide, pumice, diatomaceous earth, sulfur powder, activated carbon). Or powdered substances can be given. Liquid carriers include alcohols (e.g. methyl alcohol, ethyl alcohol), ketones (e.g. acetone, methyl ethyl ketone), ethers (e.g. ethyl ether, dioxane,
cellosolve, tetrahydrofuran), aromatic hydrocarbons (e.g. benzene, toluene, xylene, methylnaphthalene), aliphatic hydrocarbons (e.g. gasoline, kerosene, kerosene), esters,
Nitriles, acid amides (for example, methylformamide, dimethylacetamide), halogenated hydrocarbons (for example, dichloroethane, trichloroethylene, carbon tetrachloride), and the like. Next, as surfactants, alkyl sulfate esters,
Examples include alkyl sulfonates, alkylaryl sulfonates, polyethylene glycol ethers, and polyhydric alcohol esters. In addition, usable fixing agents and dispersants include casein, gelatin, starch powder, CMC, gum arabic, alginic acid, lignin sulfonate, bentonite, molasses, polyvinyl alcohol, pine oil, and agar.As stabilizers, ,for example
Examples include PAP (isopropyl phosphate), TCP (tricresyl phosphate), tall oil, epoxidized oil, various surfactants, and various fatty acids or their esters. In addition, these compounds include phenitrothion {O,O-dimethyl-O-(3-methyl-4-nitrophenyle)phosphorothioate}, marathon [S-{1,2-bis(ethoxycarbonyl)ethyl}O,O-dimethylphosphorothioate ], dimethoate {O,O-dimethyl S-(N-methylcarbamoylmethyl)phosphorodithioate},
Salithion (2-methoxy-4H-1,3,2-
benzodioxaphosphorine-2-sulfide),
Diazinon {O,O-diethyl O-(2-isopropyl-6-methyl-4-pyrimidinyl)phosphorothioate}, dipterex {2,2,2
-trichloro-1-halodroxyethyl)O,O
-dimethylphosphonate}, dichlorvos {O-
Organophosphorus insecticides such as (2,2-dichlorovinyl)O,O-dimethylphosphate}, MPMC
(3,4-dimethylphenyl N-methylcarbamate), MTMC (m-tolyl N-methylcarbamate), BPMC (2-sec-butylphenyl N-methylcarbamate), carbaryl (1-naphthyl N-methylcarbamate), etc. Carbamate insecticides, permethrin {3-phenoxybenzyl d,l-cis, trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate}, phenparerate (α-cyano -m-phenoxybenzyl α-isopropyl-
It can be mixed in any proportion with pyrethroid insecticides such as p-chlorophenyl acetate, acaricides, nematicides, fungicides, herbicides, plant growth regulators, fertilizers, soil conditioners, etc. Particularly when mixed with insecticides, stability in the efficacy of each and synergistic action can be expected. Next, some formulation examples and test examples will be shown, but the present invention is of course not limited to these. Formulation Example 1 20 parts each of the compounds (1) to (6) of the present invention, each emulsifier (polyoxyethylene styrenated phenyl ether, polyoxyethylene styrenated phenyl ether polymer, alkylaryl sulfonate mixture) ) and 60 parts of xylene and stir and mix well to obtain each emulsion. Formulation Example 2 20 parts each of the compounds (1) to (6) of the present invention are thoroughly mixed with 5 parts of an emulsifier (sodium lauryl sulfate), 75 parts of 300 mesh diatomaceous earth are added, and the mixture is sufficiently stirred in a crusher. , to obtain each hydrating agent. Formulation Example 3 3 parts each of the compounds (1) to (6) of the present invention are dissolved in 20 parts of acetone, 97 parts of 300 ml of turquoise are added, and the mixture is thoroughly stirred and mixed in a grinder, and the acetone is removed by evaporation. , to obtain each powder. Test Example 1 The juvenile hormone-like activity of the compound of the present invention was investigated using honeydew moth pupae. The method was as reported by Schneiderman (J. Insect Physiol., 1965. Vol. 11, 1641). That is,
Pupation of Honey Hemlock (Galleriamellonella) pupa20
Once collected in time, a hole of approximately 1 m 2 was drilled on the right side of its thoracic dorsum and sealed with a predetermined dose of a compound dissolved in a mixture of paraffin and peanut oil. The treated pupae were placed in a constant temperature chamber at 28°C, and the cuticle of the treated area was removed just before emergence, and the average reaction rate was determined based on the formation of the pupal cuticle . ) was sought. The results are shown in Table 2.
【表】
試験例 ２
製剤例１によつて得られた乳剤を水で400倍に
希釈し、その液0.7mlを100mlの蒸留水に加え、そ
の中にアカイエカ終令幼虫を放ち、餌を与えて羽
化まで約７日間飼育した。
結果は表３に示すとおりである（２反復）。[Table] Test Example 2 The emulsion obtained in Formulation Example 1 was diluted 400 times with water, 0.7 ml of the solution was added to 100 ml of distilled water, and Culex Culex final instar larvae were released into it and fed. The birds were reared for about 7 days until emergence. The results are shown in Table 3 (2 replicates).
【表】【table】
【表】
※ 前述に同じ
試験例 ３
製剤例１によつて得られた乳剤のうち、表４に
記載の化合物を含む乳剤を水で所定の濃度に希釈
し、その液0.5mlを100mlの蒸留水に加え、その中
にアカイエカ終令幼虫20頭を放ち餌を与え、羽化
まで約７日間飼育し、50％羽化阻害濃度（IC50
（ppm））を求めた（２反復）。結果は次式により
PI50として表４に示した。
PI50＝−logIC50 [Table] * Same test example as above 3 Among the emulsions obtained in Formulation Example 1, the emulsion containing the compounds listed in Table 4 was diluted with water to the specified concentration, and 0.5 ml of the solution was distilled into 100 ml. In addition to water, 20 terminal instar Culex Culex larvae were released into the water, fed, and reared for approximately 7 days until emergence .
(ppm)) was determined (2 repetitions). The result is given by the following formula
It is shown in Table 4 as PI 50 . PI 50 = −logIC 50
【表】
＊ 前述に同じ
試験例 ４
フスマ14ｇに粉末飼料２ｇを充分混合した。そ
の中に製剤例１で得られた乳剤のうち、表５に記
載の化合物を含む乳剤を水で所定の濃度に希釈し
た薬液を加え、撹拌混合した。こうしてできたイ
エバエ用人工培地にイエバエ終令幼虫30頭を放
ち、その中で蛹化させた。できた蛹を新しいプラ
スチツクカツプにうつし、羽化率を求め、次式に
よつて羽化阻害率を求めた。
羽化阻害率（％）＝（１−処理区羽化率／無処理区羽
化率）×
100
結果は表５に示すとおりである。[Table] * Same test example as above 4 14 g of wheat bran and 2 g of powdered feed were thoroughly mixed. A chemical solution obtained by diluting an emulsion containing the compounds listed in Table 5 with water to a predetermined concentration with water among the emulsions obtained in Formulation Example 1 was added thereto, and the mixture was stirred and mixed. Thirty final instar house fly larvae were released into the artificial medium for house flies, and pupated therein. The formed pupae were transferred to new plastic cups, the emergence rate was determined, and the emergence inhibition rate was determined using the following formula. Inhibition rate of emergence (%) = (1 - emergence rate in treated area/emergence rate in untreated area) x 100 The results are shown in Table 5.
【表】
＊ 前述に同じ
[Table] * Same as above
Claims (1)
し、R2は炭素原子数１〜３のアルキル基を表わ
し、ｍは１〜３の整数を表わし、ｎは０または１
を表わす。〕 で示されるオキシム誘導体。 ２ 一般式 〔式中、R1は水素原子またはメチル基を表わ
し、ｍは１〜３の整数を表わし、ｎは０または１
を表わす。〕 で示される化合物または該反応性誘導体と一般式 R2−Ｏ−NH2 〔式中、R2は炭素原子数１〜３のアルキル基
を表わす。〕 で示される化合物または該反応性誘導体とを反応
させることを特徴とする一般式 〔式中、R1，R2，ｍおよびｎは前述と同じ意
味を表わす。〕 で示されるオキシム誘導体の製造法。 ３ 一般式 〔式中、R1は水素原子またはメチル基を表わ
し、ｍは１〜３の整数を表わし、ｎは０または１
を表わす。〕 で示される化合物と一般式 R2−Ｘ 〔式中、R2は炭素原子数１〜３のアルキル基
を表わし、Ｘはハロゲン原子、メシルオキシ基ま
たはトシルオキシ基を表わす。〕 で示される化合物とを酸結合剤の存在下に反応さ
せることを特徴とする一般式 〔式中、R1，R2，ｍおよびｎは前述と同じ意
味を表わす。〕 で示されるオキシム誘導体の製造法。 ４ 一般式 〔式中、R1は水素原子またはメチル基を表わ
し、R2は炭素原子数１〜３のアルキル基を表わ
し、ｍは１〜３の整数を表わし、ｎは０または１
を表わす。〕 で示されるオキシム誘導体を有効成分として含有
することを特徴とする殺虫剤。[Claims] 1. General formula [In the formula, R 1 represents a hydrogen atom or a methyl group, R 2 represents an alkyl group having 1 to 3 carbon atoms, m represents an integer of 1 to 3, and n represents 0 or 1.
represents. ] An oxime derivative represented by 2 General formula [In the formula, R 1 represents a hydrogen atom or a methyl group, m represents an integer of 1 to 3, and n represents 0 or 1
represents. ] A compound or the reactive derivative represented by the general formula R 2 -O-NH 2 [wherein R 2 represents an alkyl group having 1 to 3 carbon atoms]. ] A general formula characterized by reacting with the compound represented by or the reactive derivative thereof [In the formula, R 1 , R 2 , m and n have the same meanings as above. ] A method for producing an oxime derivative shown in the following. 3 General formula [In the formula, R 1 represents a hydrogen atom or a methyl group, m represents an integer of 1 to 3, and n represents 0 or 1
represents. ] A compound represented by the general formula R 2 -X [wherein R 2 represents an alkyl group having 1 to 3 carbon atoms, and X represents a halogen atom, mesyloxy group or tosyloxy group]. ] A general formula characterized by reacting the compound represented by in the presence of an acid binder. [In the formula, R 1 , R 2 , m and n have the same meanings as above. ] A method for producing an oxime derivative shown in the following. 4 General formula [In the formula, R 1 represents a hydrogen atom or a methyl group, R 2 represents an alkyl group having 1 to 3 carbon atoms, m represents an integer of 1 to 3, and n represents 0 or 1.
represents. ] An insecticide characterized by containing an oxime derivative represented by the following as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16574983A JPS6056948A (en) | 1983-09-07 | 1983-09-07 | Oxime derivative, preparation thereof and insecticide containing the same as active constituent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16574983A JPS6056948A (en) | 1983-09-07 | 1983-09-07 | Oxime derivative, preparation thereof and insecticide containing the same as active constituent |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6056948A JPS6056948A (en) | 1985-04-02 |
| JPH043382B2 true JPH043382B2 (en) | 1992-01-23 |
Family
ID=15818342
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16574983A Granted JPS6056948A (en) | 1983-09-07 | 1983-09-07 | Oxime derivative, preparation thereof and insecticide containing the same as active constituent |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6056948A (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0200686A3 (en) * | 1985-05-02 | 1987-10-07 | Ciba-Geigy Ag | Oxime derivatives |
| JPH0430518U (en) * | 1990-07-05 | 1992-03-11 | ||
| JPH04342554A (en) * | 1991-05-20 | 1992-11-30 | Sumitomo Chem Co Ltd | 3-(4-substituted-2-chlorophenoxy)propionaldoxime ethyl ether compound, its production and noxious life controlling agent containing the same |
| JP2854538B2 (en) * | 1995-05-19 | 1999-02-03 | アイシン・エィ・ダブリュ株式会社 | Control device for linear solenoid valve |
| EA200201050A1 (en) * | 2000-04-11 | 2003-04-24 | Басф Акциенгезельшафт | METHOD OF OBTAINING OXYMAL ETHERS |
-
1983
- 1983-09-07 JP JP16574983A patent/JPS6056948A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6056948A (en) | 1985-04-02 |
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