CH616314A5 - - Google Patents
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- Publication number
- CH616314A5 CH616314A5 CH828075A CH828075A CH616314A5 CH 616314 A5 CH616314 A5 CH 616314A5 CH 828075 A CH828075 A CH 828075A CH 828075 A CH828075 A CH 828075A CH 616314 A5 CH616314 A5 CH 616314A5
- Authority
- CH
- Switzerland
- Prior art keywords
- radical
- phosphorothiolate
- carbon atoms
- propyl
- ethyl
- Prior art date
Links
- -1 phenylthio, phenylsulfinyl Chemical group 0.000 claims description 42
- 239000000203 mixture Substances 0.000 claims description 37
- 150000001875 compounds Chemical class 0.000 claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 244000045947 parasite Species 0.000 claims description 12
- 241000607479 Yersinia pestis Species 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 9
- 241000238876 Acari Species 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 241000238631 Hexapoda Species 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 239000000575 pesticide Substances 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 6
- 241000233866 Fungi Species 0.000 claims description 5
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 5
- 241000244206 Nematoda Species 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 244000052769 pathogen Species 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims 1
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 claims 1
- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 66
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 47
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 45
- 239000000243 solution Substances 0.000 description 44
- 239000000725 suspension Substances 0.000 description 35
- 239000003921 oil Substances 0.000 description 34
- 235000019198 oils Nutrition 0.000 description 34
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 24
- 238000002360 preparation method Methods 0.000 description 22
- 230000006378 damage Effects 0.000 description 19
- 238000012360 testing method Methods 0.000 description 19
- 239000000047 product Substances 0.000 description 18
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 16
- 241000196324 Embryophyta Species 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000011780 sodium chloride Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 14
- 239000012312 sodium hydride Substances 0.000 description 14
- 229910000104 sodium hydride Inorganic materials 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
- 239000000706 filtrate Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000002689 soil Substances 0.000 description 12
- 238000004587 chromatography analysis Methods 0.000 description 11
- 238000009472 formulation Methods 0.000 description 11
- 238000009835 boiling Methods 0.000 description 10
- 201000010099 disease Diseases 0.000 description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 10
- 230000000855 fungicidal effect Effects 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000007921 spray Substances 0.000 description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000000417 fungicide Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical class OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 7
- 235000013601 eggs Nutrition 0.000 description 7
- 239000002480 mineral oil Substances 0.000 description 7
- 235000010446 mineral oil Nutrition 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 241000255925 Diptera Species 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000012085 test solution Substances 0.000 description 6
- 241000907223 Bruchinae Species 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 244000046052 Phaseolus vulgaris Species 0.000 description 5
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- 239000002917 insecticide Substances 0.000 description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 230000000361 pesticidal effect Effects 0.000 description 5
- KRVHFFQFZQSNLB-UHFFFAOYSA-N 4-phenylbenzenethiol Chemical compound C1=CC(S)=CC=C1C1=CC=CC=C1 KRVHFFQFZQSNLB-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 241000257159 Musca domestica Species 0.000 description 4
- 206010033799 Paralysis Diseases 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 230000000895 acaricidal effect Effects 0.000 description 4
- 239000000642 acaricide Substances 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- NAGJZTKCGNOGPW-UHFFFAOYSA-K dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [O-]P([O-])([S-])=S NAGJZTKCGNOGPW-UHFFFAOYSA-K 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 4
- 239000005645 nematicide Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 150000007944 thiolates Chemical class 0.000 description 4
- 231100000167 toxic agent Toxicity 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- VESHAJRDDOTYSR-UHFFFAOYSA-N 3-chloro-4-(4-chlorophenyl)sulfanylphenol Chemical compound ClC1=CC(O)=CC=C1SC1=CC=C(Cl)C=C1 VESHAJRDDOTYSR-UHFFFAOYSA-N 0.000 description 3
- ATDIXWVKXAIROJ-UHFFFAOYSA-N 3-methoxy-4-phenylbenzenethiol Chemical compound COC1=CC(S)=CC=C1C1=CC=CC=C1 ATDIXWVKXAIROJ-UHFFFAOYSA-N 0.000 description 3
- GVIHOWJOFYDUJF-UHFFFAOYSA-N 3-methyl-4-phenylbenzenethiol Chemical compound CC1=CC(S)=CC=C1C1=CC=CC=C1 GVIHOWJOFYDUJF-UHFFFAOYSA-N 0.000 description 3
- MHAJLICSGFKVFK-UHFFFAOYSA-N 4-(4-chlorophenyl)sulfanylphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(Cl)C=C1 MHAJLICSGFKVFK-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 240000008067 Cucumis sativus Species 0.000 description 3
- 241000721621 Myzus persicae Species 0.000 description 3
- 241000118205 Ovicides Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000370 acceptor Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 230000012010 growth Effects 0.000 description 3
- 230000000974 larvacidal effect Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000001069 nematicidal effect Effects 0.000 description 3
- 231100000194 ovacidal Toxicity 0.000 description 3
- 230000003151 ovacidal effect Effects 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- JWUKZUIGOJBEPC-UHFFFAOYSA-N phenyl thiohypochlorite Chemical compound ClSC1=CC=CC=C1 JWUKZUIGOJBEPC-UHFFFAOYSA-N 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 239000003440 toxic substance Substances 0.000 description 3
- HORNXRXVQWOLPJ-UHFFFAOYSA-N 3-chlorophenol Chemical compound OC1=CC=CC(Cl)=C1 HORNXRXVQWOLPJ-UHFFFAOYSA-N 0.000 description 2
- ASHGTJPOSUFTGB-UHFFFAOYSA-N 3-methoxyphenol Chemical compound COC1=CC=CC(O)=C1 ASHGTJPOSUFTGB-UHFFFAOYSA-N 0.000 description 2
- OZKBCXNJYCRMLD-UHFFFAOYSA-N 4-(4-nitrophenyl)sulfanylphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C([N+]([O-])=O)C=C1 OZKBCXNJYCRMLD-UHFFFAOYSA-N 0.000 description 2
- KHMIYBLOYXKKRS-UHFFFAOYSA-N 5-chloro-2-(4-chlorophenyl)sulfanylphenol Chemical compound OC1=CC(Cl)=CC=C1SC1=CC=C(Cl)C=C1 KHMIYBLOYXKKRS-UHFFFAOYSA-N 0.000 description 2
- 241000256118 Aedes aegypti Species 0.000 description 2
- 241001388466 Bruchus rufimanus Species 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 241000931974 Leucania Species 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- 241000257226 Muscidae Species 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- ZGPJRROJOCUIEK-UHFFFAOYSA-N dihydroxy-sulfanyl-sulfanylidene-lambda5-phosphane hydrochloride Chemical compound P(O)(O)(=S)S.Cl ZGPJRROJOCUIEK-UHFFFAOYSA-N 0.000 description 2
- 235000021186 dishes Nutrition 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 238000003197 gene knockdown Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 239000002267 larvicidal agent Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 150000002903 organophosphorus compounds Chemical class 0.000 description 2
- 230000003032 phytopathogenic effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- WVTOJNFZIVWNIY-UHFFFAOYSA-N (4-chlorophenyl) thiohypochlorite Chemical compound ClSC1=CC=C(Cl)C=C1 WVTOJNFZIVWNIY-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
- KLTGKQZVXLIZPV-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)sulfanylphenol Chemical compound OC1=CC=CC=C1SC1=CC=C(Cl)C(Cl)=C1 KLTGKQZVXLIZPV-UHFFFAOYSA-N 0.000 description 1
- DSSULPPMTATCMP-UHFFFAOYSA-N 2-(4-chlorophenyl)phenol Chemical compound OC1=CC=CC=C1C1=CC=C(Cl)C=C1 DSSULPPMTATCMP-UHFFFAOYSA-N 0.000 description 1
- UJNZIFMLHOAZRY-UHFFFAOYSA-N 2-(4-chlorophenyl)sulfanylphenol Chemical compound OC1=CC=CC=C1SC1=CC=C(Cl)C=C1 UJNZIFMLHOAZRY-UHFFFAOYSA-N 0.000 description 1
- GMXMPJROWZZBTO-UHFFFAOYSA-N 2-(4-methylphenyl)sulfanylphenol Chemical compound C1=CC(C)=CC=C1SC1=CC=CC=C1O GMXMPJROWZZBTO-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- NDXZISMVZLQJDI-UHFFFAOYSA-N 2-chloro-3-(2-chlorophenyl)sulfanylphenol Chemical class OC1=CC=CC(SC=2C(=CC=CC=2)Cl)=C1Cl NDXZISMVZLQJDI-UHFFFAOYSA-N 0.000 description 1
- ZIOVDUNWSILGJC-UHFFFAOYSA-N 2-chloro-6-phenylsulfanylphenol Chemical compound OC1=C(Cl)C=CC=C1SC1=CC=CC=C1 ZIOVDUNWSILGJC-UHFFFAOYSA-N 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- UECUPGFJVNJNQA-UHFFFAOYSA-N 2-phenylbenzenethiol Chemical compound SC1=CC=CC=C1C1=CC=CC=C1 UECUPGFJVNJNQA-UHFFFAOYSA-N 0.000 description 1
- UNAKVMGQFVGWPX-UHFFFAOYSA-N 2-phenylsulfanyl-3-(trifluoromethyl)phenol Chemical compound OC1=CC=CC(C(F)(F)F)=C1SC1=CC=CC=C1 UNAKVMGQFVGWPX-UHFFFAOYSA-N 0.000 description 1
- HNHSWDPMFNORON-UHFFFAOYSA-N 4-(2-nitrophenyl)sulfanylphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=CC=C1[N+]([O-])=O HNHSWDPMFNORON-UHFFFAOYSA-N 0.000 description 1
- NRHQHEJTXFUWIZ-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)sulfanylphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(Cl)C(Cl)=C1 NRHQHEJTXFUWIZ-UHFFFAOYSA-N 0.000 description 1
- ZXNAAJFVXOECAV-UHFFFAOYSA-N 4-(3-methylphenyl)sulfanylphenol Chemical compound CC1=CC=CC(SC=2C=CC(O)=CC=2)=C1 ZXNAAJFVXOECAV-UHFFFAOYSA-N 0.000 description 1
- YJNDTOFPKRJTSR-UHFFFAOYSA-N 4-(4-chlorophenyl)sulfanyl-2-methylphenol Chemical compound C1=C(O)C(C)=CC(SC=2C=CC(Cl)=CC=2)=C1 YJNDTOFPKRJTSR-UHFFFAOYSA-N 0.000 description 1
- PQVAIVRPZSNNIE-UHFFFAOYSA-N 4-(4-chlorophenyl)sulfinylphenol Chemical compound C1=CC(O)=CC=C1S(=O)C1=CC=C(Cl)C=C1 PQVAIVRPZSNNIE-UHFFFAOYSA-N 0.000 description 1
- LFASIQLVFCSCCU-UHFFFAOYSA-N 4-(4-chlorophenyl)sulfonylphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(Cl)C=C1 LFASIQLVFCSCCU-UHFFFAOYSA-N 0.000 description 1
- KPDAZWDAQLHZNV-UHFFFAOYSA-N 4-(4-fluorophenyl)sulfanylphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(F)C=C1 KPDAZWDAQLHZNV-UHFFFAOYSA-N 0.000 description 1
- LADOBJZJEARFJO-UHFFFAOYSA-N 4-(4-methylphenyl)sulfanylphenol Chemical compound C1=CC(C)=CC=C1SC1=CC=C(O)C=C1 LADOBJZJEARFJO-UHFFFAOYSA-N 0.000 description 1
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 1
- BRKOMYZFHCHELV-UHFFFAOYSA-N 4-chloro-2-phenylsulfanylphenol Chemical compound OC1=CC=C(Cl)C=C1SC1=CC=CC=C1 BRKOMYZFHCHELV-UHFFFAOYSA-N 0.000 description 1
- VZXOZSQDJJNBRC-UHFFFAOYSA-N 4-chlorobenzenethiol Chemical compound SC1=CC=C(Cl)C=C1 VZXOZSQDJJNBRC-UHFFFAOYSA-N 0.000 description 1
- NKZXKUSROCSYRT-UHFFFAOYSA-N 4-methoxy-2-phenylsulfanylphenol Chemical compound COC1=CC=C(O)C(SC=2C=CC=CC=2)=C1 NKZXKUSROCSYRT-UHFFFAOYSA-N 0.000 description 1
- DXYCKRHEPIOUIU-UHFFFAOYSA-N 4-methyl-2-phenylsulfanylphenol Chemical compound CC1=CC=C(O)C(SC=2C=CC=CC=2)=C1 DXYCKRHEPIOUIU-UHFFFAOYSA-N 0.000 description 1
- SDFXHGHYTJVNSO-UHFFFAOYSA-N 4-phenylsulfanyl-3-(trifluoromethyl)phenol Chemical compound FC(F)(F)C1=CC(O)=CC=C1SC1=CC=CC=C1 SDFXHGHYTJVNSO-UHFFFAOYSA-N 0.000 description 1
- 244000066764 Ailanthus triphysa Species 0.000 description 1
- 241000254175 Anthonomus grandis Species 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 241000239290 Araneae Species 0.000 description 1
- 241000238421 Arthropoda Species 0.000 description 1
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- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 1
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 1
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 1
- 244000308180 Brassica oleracea var. italica Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- 235000009849 Cucumis sativus Nutrition 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- 241000256113 Culicidae Species 0.000 description 1
- 241000489976 Diabrotica undecimpunctata howardi Species 0.000 description 1
- 241000462639 Epilachna varivestis Species 0.000 description 1
- 241000896222 Erysiphe polygoni Species 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 241000282414 Homo sapiens Species 0.000 description 1
- 241000243786 Meloidogyne incognita Species 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 241000488583 Panonychus ulmi Species 0.000 description 1
- 241000233679 Peronosporaceae Species 0.000 description 1
- 241000219833 Phaseolus Species 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 206010035148 Plague Diseases 0.000 description 1
- 241001281803 Plasmopara viticola Species 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 241001123569 Puccinia recondita Species 0.000 description 1
- 241001071900 Scapanus orarius Species 0.000 description 1
- 241001521235 Spodoptera eridania Species 0.000 description 1
- 241001494115 Stomoxys calcitrans Species 0.000 description 1
- 241001454293 Tetranychus urticae Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 244000098338 Triticum aestivum Species 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000009418 agronomic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 210000000576 arachnoid Anatomy 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 238000012925 biological evaluation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- TXHWYSOQHNMOOU-UHFFFAOYSA-N chloro(diethoxy)phosphane Chemical compound CCOP(Cl)OCC TXHWYSOQHNMOOU-UHFFFAOYSA-N 0.000 description 1
- DQTRYXANLKJLPK-UHFFFAOYSA-N chlorophosphonous acid Chemical compound OP(O)Cl DQTRYXANLKJLPK-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- GQDAQMBBGHMTQX-UHFFFAOYSA-N dihydroxy-propylsulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound CCCSP(O)(O)=S GQDAQMBBGHMTQX-UHFFFAOYSA-N 0.000 description 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 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
- 238000004821 distillation Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 244000078703 ectoparasite Species 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 244000079386 endoparasite Species 0.000 description 1
- 230000008029 eradication Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 230000003129 miticidal effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000012797 qualification Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910000679 solder Chemical group 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000012795 verification Methods 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/14—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing aromatic radicals
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/18—Esters of thiophosphoric acids with hydroxyaryl compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US48319074A | 1974-06-26 | 1974-06-26 | |
| US05/576,836 US4029774A (en) | 1974-06-26 | 1975-05-12 | O,S-dialkyl O -phenylthio-phenyl phosphorothiolates/phosphorodithioates and their derivatives and pesticidal use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH616314A5 true CH616314A5 (xx) | 1980-03-31 |
Family
ID=27047561
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH828075A CH616314A5 (xx) | 1974-06-26 | 1975-06-25 |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4029774A (xx) |
| JP (1) | JPS5945649B2 (xx) |
| AR (1) | AR209307A1 (xx) |
| AT (1) | AT348828B (xx) |
| BG (1) | BG33272A3 (xx) |
| BR (1) | BR7503937A (xx) |
| CA (1) | CA1052808A (xx) |
| CH (1) | CH616314A5 (xx) |
| CS (1) | CS191269B2 (xx) |
| DD (1) | DD118515A5 (xx) |
| DE (1) | DE2527308C2 (xx) |
| DK (1) | DK144600C (xx) |
| ES (1) | ES439062A1 (xx) |
| FR (1) | FR2276311A1 (xx) |
| GB (1) | GB1509019A (xx) |
| HU (1) | HU175157B (xx) |
| IE (1) | IE41158B1 (xx) |
| IL (1) | IL47564A (xx) |
| IN (1) | IN140974B (xx) |
| IT (1) | IT1044509B (xx) |
| MX (1) | MX3499E (xx) |
| NL (1) | NL179058C (xx) |
| OA (1) | OA05038A (xx) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3700997A (en) * | 1971-02-24 | 1972-10-24 | Mcculloch Corp | Rapid charging of batteries |
| JPS4915935A (en) * | 1972-06-08 | 1974-02-12 | Sony Corp | Battery charging device |
| JPS50110040A (xx) * | 1974-02-12 | 1975-08-29 | ||
| GB1585963A (en) * | 1976-10-14 | 1981-03-11 | Lilly Industries Ltd | Aryl sulphur compounds |
| IL57962A0 (en) * | 1978-08-21 | 1979-12-30 | Kumiai Chemical Industry Co | Organic phosphoric ester derivatives their preparation and bacteriocidal insecticidal and miticidal compositions containing them |
| US4650792A (en) * | 1980-07-18 | 1987-03-17 | Dennis Underwood | Mosquito abatement |
| US10072256B2 (en) * | 2006-05-22 | 2018-09-11 | Abbott Products Gmbh | Process for separating and determining the viral load in a pancreatin sample |
| CN114213454B (zh) * | 2021-12-24 | 2024-02-20 | 河北威远生物化工有限公司 | 一种连续化合成o-乙基-s-仲丁基硫代磷酰氯的方法 |
| CN115385950B (zh) * | 2022-10-27 | 2023-04-28 | 天津凯莱英医药科技发展有限公司 | 连续臭氧氧化制备4-乙酰氧基氮杂环丁酮的系统及方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE556009A (xx) * | 1956-03-22 | |||
| NL135594C (xx) * | 1961-06-06 | |||
| DE1193036B (de) * | 1962-12-22 | 1965-05-20 | Bayer Ag | Verfahren zur Herstellung von Phosphor-, Phosphon-, Phosphin- bzw. Thiophosphor-, -phosphon-, -phosphinsaeureestern |
| JPS4924656B1 (xx) * | 1970-03-13 | 1974-06-25 | ||
| US3839511A (en) * | 1970-12-26 | 1974-10-01 | Bayer Ag | O-ethyl-s-n-propyl-o-(substituted phenyl)-phosphorothiolates |
| CA1058192A (en) * | 1972-11-03 | 1979-07-10 | Ciba-Geigy Ag | Esters |
-
1975
- 1975-05-12 US US05/576,836 patent/US4029774A/en not_active Expired - Lifetime
- 1975-06-04 CA CA228,511A patent/CA1052808A/en not_active Expired
- 1975-06-13 IE IE1337/75A patent/IE41158B1/xx unknown
- 1975-06-16 DK DK270775A patent/DK144600C/da not_active IP Right Cessation
- 1975-06-16 AR AR259210A patent/AR209307A1/es active
- 1975-06-17 IN IN1200/CAL/1975A patent/IN140974B/en unknown
- 1975-06-19 DE DE2527308A patent/DE2527308C2/de not_active Expired
- 1975-06-20 GB GB26234/75A patent/GB1509019A/en not_active Expired
- 1975-06-24 MX MX756360U patent/MX3499E/es unknown
- 1975-06-24 BR BR5062/75D patent/BR7503937A/pt unknown
- 1975-06-25 IL IL47564A patent/IL47564A/xx unknown
- 1975-06-25 AT AT487275A patent/AT348828B/de not_active IP Right Cessation
- 1975-06-25 JP JP50079294A patent/JPS5945649B2/ja not_active Expired
- 1975-06-25 FR FR7519926A patent/FR2276311A1/fr active Granted
- 1975-06-25 CH CH828075A patent/CH616314A5/fr not_active IP Right Cessation
- 1975-06-25 IT IT68637/75A patent/IT1044509B/it active
- 1975-06-25 HU HU76RO842A patent/HU175157B/hu unknown
- 1975-06-25 DD DD186879A patent/DD118515A5/xx unknown
- 1975-06-25 OA OA55537A patent/OA05038A/xx unknown
- 1975-06-26 BG BG030404A patent/BG33272A3/xx unknown
- 1975-06-26 CS CS754552A patent/CS191269B2/cs unknown
- 1975-06-26 ES ES439062A patent/ES439062A1/es not_active Expired
- 1975-06-26 NL NLAANVRAGE7507648,A patent/NL179058C/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2527308A1 (de) | 1976-01-15 |
| HU175157B (hu) | 1980-05-28 |
| JPS5945649B2 (ja) | 1984-11-07 |
| BG33272A3 (en) | 1983-01-14 |
| MX3499E (es) | 1981-01-05 |
| FR2276311A1 (fr) | 1976-01-23 |
| NL7507648A (nl) | 1975-12-30 |
| DK270775A (da) | 1975-12-27 |
| DE2527308C2 (de) | 1983-11-24 |
| DD118515A5 (xx) | 1976-03-12 |
| NL179058C (nl) | 1986-07-01 |
| IN140974B (xx) | 1977-01-08 |
| DK144600C (da) | 1982-10-04 |
| IL47564A0 (en) | 1975-08-31 |
| NL179058B (nl) | 1986-02-03 |
| GB1509019A (en) | 1978-04-26 |
| FR2276311B1 (xx) | 1977-12-02 |
| JPS5119131A (xx) | 1976-02-16 |
| OA05038A (fr) | 1980-12-31 |
| CS191269B2 (en) | 1979-06-29 |
| US4029774A (en) | 1977-06-14 |
| BR7503937A (pt) | 1976-07-06 |
| CA1052808A (en) | 1979-04-17 |
| IT1044509B (it) | 1980-03-31 |
| ES439062A1 (es) | 1977-08-01 |
| IE41158L (en) | 1975-12-26 |
| DK144600B (da) | 1982-04-13 |
| IE41158B1 (en) | 1979-10-24 |
| ATA487275A (de) | 1978-07-15 |
| AR209307A1 (es) | 1977-04-15 |
| AT348828B (de) | 1979-03-12 |
| AU8230375A (en) | 1976-12-23 |
| IL47564A (en) | 1978-06-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |