AP28A - Insecticidal alkenes. - Google Patents
Insecticidal alkenes. Download PDFInfo
- Publication number
- AP28A AP28A APAP/P/1986/000043A AP8600043A AP28A AP 28 A AP28 A AP 28A AP 8600043 A AP8600043 A AP 8600043A AP 28 A AP28 A AP 28A
- Authority
- AP
- ARIPO
- Prior art keywords
- compound
- fluoro
- hydrogen
- formula
- dimethyl
- Prior art date
Links
- 230000000749 insecticidal effect Effects 0.000 title claims description 5
- 150000001336 alkenes Chemical class 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 72
- 150000001875 compounds Chemical class 0.000 claims abstract description 52
- -1 phenoxy phenyl group Chemical group 0.000 claims abstract description 23
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 241000607479 Yersinia pestis Species 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 24
- 239000004480 active ingredient Substances 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 241000238631 Hexapoda Species 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 238000007239 Wittig reaction Methods 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 239000001273 butane Substances 0.000 claims description 2
- 239000003701 inert diluent Substances 0.000 claims description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 3
- NZODPCQZQSWRNP-FOCLMDBBSA-N 4-[[(e)-2,2-dimethyl-4-(4-methylphenyl)but-3-enoxy]methyl]-1-fluoro-2-phenoxybenzene Chemical compound C1=CC(C)=CC=C1\C=C\C(C)(C)COCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 NZODPCQZQSWRNP-FOCLMDBBSA-N 0.000 claims 1
- 102100040141 Aminopeptidase O Human genes 0.000 claims 1
- 108050008333 Aminopeptidase O Proteins 0.000 claims 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 239000002917 insecticide Substances 0.000 abstract description 12
- 239000000543 intermediate Substances 0.000 abstract description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 81
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 48
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 238000002360 preparation method Methods 0.000 description 30
- 239000000047 product Substances 0.000 description 26
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 25
- 229960004132 diethyl ether Drugs 0.000 description 25
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 21
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 20
- 239000003921 oil Substances 0.000 description 19
- 235000019198 oils Nutrition 0.000 description 19
- 239000003480 eluent Substances 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 15
- 239000007788 liquid Substances 0.000 description 15
- 238000001704 evaporation Methods 0.000 description 13
- 230000008020 evaporation Effects 0.000 description 13
- 238000004817 gas chromatography Methods 0.000 description 13
- 239000000725 suspension Substances 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 229940093499 ethyl acetate Drugs 0.000 description 11
- 235000019439 ethyl acetate Nutrition 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 10
- 235000019341 magnesium sulphate Nutrition 0.000 description 10
- 125000001309 chloro group Chemical group Cl* 0.000 description 9
- 239000000284 extract Substances 0.000 description 9
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 8
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical group [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 241000209094 Oryza Species 0.000 description 7
- 235000007164 Oryza sativa Nutrition 0.000 description 7
- 239000012141 concentrate Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 235000009566 rice Nutrition 0.000 description 7
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical class C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 7
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- RAFLWVRGEUNWLN-UHFFFAOYSA-N 3-[(4-fluoro-3-phenoxyphenyl)methoxy]-2,2-dimethylpropanal Chemical compound O=CC(C)(C)COCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 RAFLWVRGEUNWLN-UHFFFAOYSA-N 0.000 description 5
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- 239000000080 wetting agent Substances 0.000 description 5
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 4
- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 239000003995 emulsifying agent Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000000417 fungicide Substances 0.000 description 4
- 239000004009 herbicide Substances 0.000 description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 4
- DWIYANXFWXPJQY-UHFFFAOYSA-M (4-fluorophenyl)methyl-triphenylphosphanium;bromide Chemical compound [Br-].C1=CC(F)=CC=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 DWIYANXFWXPJQY-UHFFFAOYSA-M 0.000 description 3
- CTJIGYSODYOMGI-UHFFFAOYSA-N 1-(bromomethyl)-3,5-dichlorobenzene Chemical compound ClC1=CC(Cl)=CC(CBr)=C1 CTJIGYSODYOMGI-UHFFFAOYSA-N 0.000 description 3
- DCLMJYZEOSDVCL-UHFFFAOYSA-N 1-(chloromethyl)-4-ethoxybenzene Chemical compound CCOC1=CC=C(CCl)C=C1 DCLMJYZEOSDVCL-UHFFFAOYSA-N 0.000 description 3
- UQQRMQJWHACSPY-UHFFFAOYSA-N 2,2-dimethyl-3-[(3-phenoxyphenyl)methoxy]propan-1-ol Chemical compound OCC(C)(C)COCC1=CC=CC(OC=2C=CC=CC=2)=C1 UQQRMQJWHACSPY-UHFFFAOYSA-N 0.000 description 3
- DQHAFABSSNVWEJ-UHFFFAOYSA-N 2,2-dimethyl-3-[(3-phenoxyphenyl)methoxy]propanal Chemical compound O=CC(C)(C)COCC1=CC=CC(OC=2C=CC=CC=2)=C1 DQHAFABSSNVWEJ-UHFFFAOYSA-N 0.000 description 3
- 239000005660 Abamectin Substances 0.000 description 3
- 241000251468 Actinopterygii Species 0.000 description 3
- 241001124076 Aphididae Species 0.000 description 3
- 241000426499 Chilo Species 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 241000257159 Musca domestica Species 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 241000344246 Tetranychus cinnabarinus Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000005648 plant growth regulator Substances 0.000 description 3
- KFMPZHBLRRGZPN-UHFFFAOYSA-M (4-chlorophenyl)methyl-triphenylphosphanium;bromide Chemical compound [Br-].C1=CC(Cl)=CC=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 KFMPZHBLRRGZPN-UHFFFAOYSA-M 0.000 description 2
- UKFLLQIRBABMKF-UHFFFAOYSA-N (4-ethoxyphenyl)methanol Chemical compound CCOC1=CC=C(CO)C=C1 UKFLLQIRBABMKF-UHFFFAOYSA-N 0.000 description 2
- DAHDOAWPHZYRNB-UHFFFAOYSA-M (4-fluorophenyl)-triphenylphosphanium;bromide Chemical compound [Br-].C1=CC(F)=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 DAHDOAWPHZYRNB-UHFFFAOYSA-M 0.000 description 2
- CEEKCHGNKYVTTM-UHFFFAOYSA-M (4-methylphenyl)methyl-triphenylphosphanium;bromide Chemical compound [Br-].C1=CC(C)=CC=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 CEEKCHGNKYVTTM-UHFFFAOYSA-M 0.000 description 2
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- SCBZBMXPJYMXRC-UHFFFAOYSA-N 1-(bromomethyl)-3-fluorobenzene Chemical compound FC1=CC=CC(CBr)=C1 SCBZBMXPJYMXRC-UHFFFAOYSA-N 0.000 description 2
- XTCFXTPNWBJYNS-UHFFFAOYSA-N 1-[3,3-dimethyl-4-[(3-phenoxyphenyl)methoxy]but-1-enyl]-4-(trifluoromethyl)benzene Chemical compound C=1C=C(C(F)(F)F)C=CC=1C=CC(C)(C)COCC(C=1)=CC=CC=1OC1=CC=CC=C1 XTCFXTPNWBJYNS-UHFFFAOYSA-N 0.000 description 2
- XLNYEJKLBFOYFW-UHFFFAOYSA-N 1-[3,3-dimethyl-4-[(3-phenoxyphenyl)methoxy]but-1-enyl]-4-ethoxybenzene Chemical compound C1=CC(OCC)=CC=C1C=CC(C)(C)COCC1=CC=CC(OC=2C=CC=CC=2)=C1 XLNYEJKLBFOYFW-UHFFFAOYSA-N 0.000 description 2
- XZXYQEHISUMZAT-UHFFFAOYSA-N 2-[(2-hydroxy-5-methylphenyl)methyl]-4-methylphenol Chemical compound CC1=CC=C(O)C(CC=2C(=CC=C(C)C=2)O)=C1 XZXYQEHISUMZAT-UHFFFAOYSA-N 0.000 description 2
- OPPFLKUKMPLPOE-UHFFFAOYSA-N 2-methyl-2-[(3-phenoxyphenyl)methoxymethyl]butan-1-ol Chemical compound CCC(C)(CO)COCC1=CC=CC(OC=2C=CC=CC=2)=C1 OPPFLKUKMPLPOE-UHFFFAOYSA-N 0.000 description 2
- CBQDTCDOVVBGMN-UHFFFAOYSA-N 2-methyl-3-octylphenol Chemical compound CCCCCCCCC1=CC=CC(O)=C1C CBQDTCDOVVBGMN-UHFFFAOYSA-N 0.000 description 2
- DUIOKRXOKLLURE-UHFFFAOYSA-N 2-octylphenol Chemical compound CCCCCCCCC1=CC=CC=C1O DUIOKRXOKLLURE-UHFFFAOYSA-N 0.000 description 2
- RQBSITCQIWIGPD-UHFFFAOYSA-N 3-[(4-fluoro-3-phenoxyphenyl)methoxy]-2,2-dimethylpropan-1-ol Chemical compound OCC(C)(C)COCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 RQBSITCQIWIGPD-UHFFFAOYSA-N 0.000 description 2
- NDUYSHSMFJHTAZ-UHFFFAOYSA-N 4-(2,2-dimethylbut-3-enoxymethyl)-1-fluoro-2-phenoxybenzene Chemical compound C=CC(C)(C)COCC1=CC=C(F)C(OC=2C=CC=CC=2)=C1 NDUYSHSMFJHTAZ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 241000353522 Earias insulana Species 0.000 description 2
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- 206010061217 Infestation Diseases 0.000 description 2
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- 241001608567 Phaedon cochleariae Species 0.000 description 2
- 241000500437 Plutella xylostella Species 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- 239000004141 Sodium laurylsulphate Substances 0.000 description 2
- 241000256250 Spodoptera littoralis Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
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- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical class 0.000 description 2
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- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 2
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- JIJAYWGYIDJVJI-UHFFFAOYSA-N butyl naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)OCCCC)=CC=CC2=C1 JIJAYWGYIDJVJI-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
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- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
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- 235000010445 lecithin Nutrition 0.000 description 2
- 150000004668 long chain fatty acids Chemical class 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 2
- 229940055577 oleyl alcohol Drugs 0.000 description 2
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 2
- 239000010502 orange oil Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- QYMMJNLHFKGANY-UHFFFAOYSA-N profenofos Chemical compound CCCSP(=O)(OCC)OC1=CC=C(Br)C=C1Cl QYMMJNLHFKGANY-UHFFFAOYSA-N 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- HFQQZARZPUDIFP-UHFFFAOYSA-M sodium;2-dodecylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O HFQQZARZPUDIFP-UHFFFAOYSA-M 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
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- NNKVPIKMPCQWCG-UHFFFAOYSA-N methamidophos Chemical compound COP(N)(=O)SC NNKVPIKMPCQWCG-UHFFFAOYSA-N 0.000 description 1
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- LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 1
- FXWHFKOXMBTCMP-WMEDONTMSA-N milbemycin Natural products COC1C2OCC3=C/C=C/C(C)CC(=CCC4CC(CC5(O4)OC(C)C(C)C(OC(=O)C(C)CC(C)C)C5O)OC(=O)C(C=C1C)C23O)C FXWHFKOXMBTCMP-WMEDONTMSA-N 0.000 description 1
- KRTSDMXIXPKRQR-AATRIKPKSA-N monocrotophos Chemical compound CNC(=O)\C=C(/C)OP(=O)(OC)OC KRTSDMXIXPKRQR-AATRIKPKSA-N 0.000 description 1
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- 150000004045 organic chlorine compounds Chemical class 0.000 description 1
- KZAUOCCYDRDERY-UHFFFAOYSA-N oxamyl Chemical compound CNC(=O)ON=C(SC)C(=O)N(C)C KZAUOCCYDRDERY-UHFFFAOYSA-N 0.000 description 1
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- 229910052763 palladium Inorganic materials 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 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
- 239000003016 pheromone Substances 0.000 description 1
- BULVZWIRKLYCBC-UHFFFAOYSA-N phorate Chemical compound CCOP(=S)(OCC)SCSCC BULVZWIRKLYCBC-UHFFFAOYSA-N 0.000 description 1
- RGCLLPNLLBQHPF-HJWRWDBZSA-N phosphamidon Chemical compound CCN(CC)C(=O)C(\Cl)=C(/C)OP(=O)(OC)OC RGCLLPNLLBQHPF-HJWRWDBZSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- ATROHALUCMTWTB-OWBHPGMISA-N phoxim Chemical compound CCOP(=S)(OCC)O\N=C(\C#N)C1=CC=CC=C1 ATROHALUCMTWTB-OWBHPGMISA-N 0.000 description 1
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- YFGYUFNIOHWBOB-UHFFFAOYSA-N pirimicarb Chemical compound CN(C)C(=O)OC1=NC(N(C)C)=NC(C)=C1C YFGYUFNIOHWBOB-UHFFFAOYSA-N 0.000 description 1
- QHOQHJPRIBSPCY-UHFFFAOYSA-N pirimiphos-methyl Chemical group CCN(CC)C1=NC(C)=CC(OP(=S)(OC)OC)=N1 QHOQHJPRIBSPCY-UHFFFAOYSA-N 0.000 description 1
- LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- SMKRKQBMYOFFMU-UHFFFAOYSA-N prallethrin Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OC1C(C)=C(CC#C)C(=O)C1 SMKRKQBMYOFFMU-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
- ZYHMJXZULPZUED-UHFFFAOYSA-N propargite Chemical compound C1=CC(C(C)(C)C)=CC=C1OC1C(OS(=O)OCC#C)CCCC1 ZYHMJXZULPZUED-UHFFFAOYSA-N 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- HYJYGLGUBUDSLJ-UHFFFAOYSA-N pyrethrin Natural products CCC(=O)OC1CC(=C)C2CC3OC3(C)C2C2OC(=O)C(=C)C12 HYJYGLGUBUDSLJ-UHFFFAOYSA-N 0.000 description 1
- VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical compound CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VJFUPGQZSXIULQ-XIGJTORUSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 239000001476 sodium potassium tartrate Substances 0.000 description 1
- 235000011006 sodium potassium tartrate Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
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- JXHJNEJVUNHLKO-UHFFFAOYSA-N sulprofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(SC)C=C1 JXHJNEJVUNHLKO-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
- 229960005199 tetramethrin Drugs 0.000 description 1
- OPASCBHCTNRLRM-UHFFFAOYSA-N thiometon Chemical compound CCSCCSP(=S)(OC)OC OPASCBHCTNRLRM-UHFFFAOYSA-N 0.000 description 1
- 101150068774 thyX gene Proteins 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- XQTOXOYESAZYHS-UHFFFAOYSA-M triphenyl-[4-(trifluoromethyl)phenyl]phosphanium;bromide Chemical compound [Br-].C1=CC(C(F)(F)F)=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 XQTOXOYESAZYHS-UHFFFAOYSA-M 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 231100000925 very toxic Toxicity 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N γ Benzene hexachloride Chemical compound ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5456—Arylalkanephosphonium compounds
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
- A01N31/14—Ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
- C07C43/267—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
- C07C43/285—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings having unsaturation outside the six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
- C07C43/29—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/257—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings
- C07C43/295—Ethers having an ether-oxygen atom bound to carbon atoms both belonging to six-membered aromatic rings containing hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/30—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation
- C07C45/305—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation with halogenochromate reagents, e.g. pyridinium chlorochromate
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/277—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Biochemistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB858523464A GB8523464D0 (en) | 1985-09-23 | 1985-09-23 | Insecticidal alkenes |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AP8600043A0 AP8600043A0 (en) | 1986-08-01 |
| AP28A true AP28A (en) | 1988-12-20 |
Family
ID=10585608
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| APAP/P/1986/000043A AP28A (en) | 1985-09-23 | 1986-09-05 | Insecticidal alkenes. |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4705900A (ja) |
| EP (1) | EP0220810B1 (ja) |
| JP (1) | JPS6272642A (ja) |
| CN (1) | CN1016336B (ja) |
| AP (1) | AP28A (ja) |
| AT (1) | ATE53831T1 (ja) |
| AU (1) | AU6259386A (ja) |
| BR (1) | BR8604472A (ja) |
| DE (1) | DE3670837D1 (ja) |
| ES (1) | ES2001980A6 (ja) |
| GB (2) | GB8523464D0 (ja) |
| GR (1) | GR862392B (ja) |
| HU (1) | HU202054B (ja) |
| IL (1) | IL79983A (ja) |
| MY (1) | MY100142A (ja) |
| NZ (1) | NZ217451A (ja) |
| OA (1) | OA08414A (ja) |
| PT (1) | PT83413B (ja) |
| ZA (1) | ZA866660B (ja) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5248834A (en) * | 1984-04-09 | 1993-09-28 | British Technology Group Limited | Pesticides |
| US4788348A (en) * | 1987-08-12 | 1988-11-29 | Imperial Chemical Industries Plc | Insecticidal alkenes |
| US4900758A (en) * | 1989-05-11 | 1990-02-13 | Ici Americas Inc. | Novel insecticides |
| US5635194A (en) * | 1993-11-12 | 1997-06-03 | Shell Oil Company | Detergent range ethoxylated alcohols to control black flies |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1579839A (en) * | 1977-04-16 | 1980-11-26 | Lafon Labor | Chlorophenoxybenzene derivatives |
| DE3317908A1 (de) * | 1982-05-18 | 1983-12-22 | Mitsui Toatsu Chemicals, Inc., Tokyo | Neue aromatische alkanderivate, verfahren zu ihrer herstellung und solch ein derivat als aktiven bestandteil enthaltende insektizide und akarizide mittel |
| EP0125204A1 (de) * | 1983-04-12 | 1984-11-14 | Ciba-Geigy Ag | 3-Phenoxybenzyl-(2-phenyl-2,2-alkylen-äthyl)-äther und -thioäther, Verfahren zu ihrer Herstellung und ihre Verwendung in der Schädlingsbekämpfung |
| JPS59225135A (ja) * | 1983-06-06 | 1984-12-18 | Sumitomo Chem Co Ltd | エ−テル誘導体、その製造法およびそれを有効成分とする殺虫、殺ダニ剤 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3078256A (en) * | 1954-09-24 | 1963-02-19 | Basf Ag | Production of unsaturated compounds |
| US2913498A (en) * | 1956-09-18 | 1959-11-17 | Metal & Thermit Corp | Process for preparing aromatic phosphorus compounds |
| US3379752A (en) * | 1964-05-20 | 1968-04-23 | Merck & Co Inc | Phenoxy substituted 3-hydroxyalkanoic acids and a method for their preparation |
| US3418377A (en) * | 1965-03-15 | 1968-12-24 | Dow Chemical Co | Diphenyl ether polyols |
| US3444216A (en) * | 1966-11-16 | 1969-05-13 | Upjohn Co | Process for the oxidation of primary and secondary alcohols |
| US3726886A (en) * | 1970-12-07 | 1973-04-10 | Dow Chemical Co | Adducts of alkenyl isocyanates with hydroxymethylated diphenyl oxide and derivatives thereof |
| CA1051031A (en) * | 1974-06-21 | 1979-03-20 | The Dow Chemical Company | Latent catalysts for promoting reaction of epoxides with phenols and/or carboxylic acids |
| DE2502786A1 (de) * | 1975-01-24 | 1976-07-29 | Merck Patent Gmbh | Diphenylaether-derivate und verfahren zu ihrer herstellung |
| GB1570982A (en) * | 1976-03-05 | 1980-07-09 | Shell Int Research | Substituted benzyl ethers and thioethers |
| US4397864A (en) * | 1980-05-02 | 1983-08-09 | Mitsuitoatsu Chemicals Inc. | 2-Arylpropyl ether or thioether derivatives and insecticidal and acaricidal agents containing said derivatives |
| JPS5764632A (en) * | 1980-10-09 | 1982-04-19 | Mitsui Toatsu Chem Inc | Novel 2-arylethyl ether derivative and thioether derivative, their production and insecticide and acaricide |
| SE461790B (sv) * | 1982-10-19 | 1990-03-26 | Mitsui Toatsu Chemicals | Foerfarande foer framstaellning av 3-fenoxibensyl-2-(4-alkoxifenyl)-2-metylpropyletrar |
| GB8311678D0 (en) * | 1983-04-28 | 1983-06-02 | Ici Plc | Phenol derivatives |
-
1985
- 1985-09-23 GB GB858523464A patent/GB8523464D0/en active Pending
-
1986
- 1986-08-26 AT AT86306586T patent/ATE53831T1/de not_active IP Right Cessation
- 1986-08-26 GB GB8620645A patent/GB2180838B/en not_active Expired
- 1986-08-26 EP EP86306586A patent/EP0220810B1/en not_active Expired - Lifetime
- 1986-08-26 DE DE8686306586T patent/DE3670837D1/de not_active Expired - Fee Related
- 1986-09-02 ZA ZA866660A patent/ZA866660B/xx unknown
- 1986-09-03 US US06/903,244 patent/US4705900A/en not_active Expired - Fee Related
- 1986-09-03 NZ NZ217451A patent/NZ217451A/xx unknown
- 1986-09-05 AP APAP/P/1986/000043A patent/AP28A/en active
- 1986-09-09 IL IL79983A patent/IL79983A/xx unknown
- 1986-09-11 AU AU62593/86A patent/AU6259386A/en not_active Abandoned
- 1986-09-18 BR BR8604472A patent/BR8604472A/pt not_active Application Discontinuation
- 1986-09-18 GR GR862392A patent/GR862392B/el unknown
- 1986-09-19 OA OA58958A patent/OA08414A/xx unknown
- 1986-09-22 JP JP61222241A patent/JPS6272642A/ja active Pending
- 1986-09-22 HU HU864008A patent/HU202054B/hu not_active IP Right Cessation
- 1986-09-22 PT PT83413A patent/PT83413B/pt not_active IP Right Cessation
- 1986-09-23 ES ES8602112A patent/ES2001980A6/es not_active Expired
- 1986-09-23 CN CN86106692A patent/CN1016336B/zh not_active Expired
-
1987
- 1987-08-07 MY MYPI87001230A patent/MY100142A/en unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1579839A (en) * | 1977-04-16 | 1980-11-26 | Lafon Labor | Chlorophenoxybenzene derivatives |
| DE3317908A1 (de) * | 1982-05-18 | 1983-12-22 | Mitsui Toatsu Chemicals, Inc., Tokyo | Neue aromatische alkanderivate, verfahren zu ihrer herstellung und solch ein derivat als aktiven bestandteil enthaltende insektizide und akarizide mittel |
| EP0125204A1 (de) * | 1983-04-12 | 1984-11-14 | Ciba-Geigy Ag | 3-Phenoxybenzyl-(2-phenyl-2,2-alkylen-äthyl)-äther und -thioäther, Verfahren zu ihrer Herstellung und ihre Verwendung in der Schädlingsbekämpfung |
| JPS59225135A (ja) * | 1983-06-06 | 1984-12-18 | Sumitomo Chem Co Ltd | エ−テル誘導体、その製造法およびそれを有効成分とする殺虫、殺ダニ剤 |
Also Published As
| Publication number | Publication date |
|---|---|
| HU202054B (en) | 1991-02-28 |
| GB8620645D0 (en) | 1986-10-01 |
| GR862392B (en) | 1986-11-18 |
| CN1016336B (zh) | 1992-04-22 |
| OA08414A (fr) | 1988-06-30 |
| CN86106692A (zh) | 1987-03-18 |
| AP8600043A0 (en) | 1986-08-01 |
| MY100142A (en) | 1990-01-18 |
| GB8523464D0 (en) | 1985-10-30 |
| AU6259386A (en) | 1987-03-26 |
| GB2180838A (en) | 1987-04-08 |
| JPS6272642A (ja) | 1987-04-03 |
| GB2180838B (en) | 1989-09-06 |
| ATE53831T1 (de) | 1990-06-15 |
| EP0220810B1 (en) | 1990-05-02 |
| IL79983A (en) | 1992-05-25 |
| US4705900A (en) | 1987-11-10 |
| NZ217451A (en) | 1989-10-27 |
| EP0220810A1 (en) | 1987-05-06 |
| BR8604472A (pt) | 1987-05-19 |
| IL79983A0 (en) | 1986-12-31 |
| DE3670837D1 (de) | 1990-06-07 |
| ES2001980A6 (es) | 1988-07-01 |
| HUT41593A (en) | 1987-05-28 |
| PT83413A (en) | 1986-10-01 |
| ZA866660B (en) | 1987-05-27 |
| PT83413B (pt) | 1989-05-12 |
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