DE2724494A1 - Verfahren zur kontrolle von milben- und insekten-schaedlingen, milben- und insektenbekaempfungsmittel und substituierte thiophene - Google Patents
Verfahren zur kontrolle von milben- und insekten-schaedlingen, milben- und insektenbekaempfungsmittel und substituierte thiopheneInfo
- Publication number
- DE2724494A1 DE2724494A1 DE19772724494 DE2724494A DE2724494A1 DE 2724494 A1 DE2724494 A1 DE 2724494A1 DE 19772724494 DE19772724494 DE 19772724494 DE 2724494 A DE2724494 A DE 2724494A DE 2724494 A1 DE2724494 A1 DE 2724494A1
- Authority
- DE
- Germany
- Prior art keywords
- thiophene
- phenyl
- carbon atoms
- diphenylthiophene
- phenylthio
- 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.)
- Pending
Links
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical class C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 title claims description 100
- 229930192474 thiophene Natural products 0.000 title claims description 65
- 238000000034 method Methods 0.000 title claims description 15
- 241000238631 Hexapoda Species 0.000 title claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 79
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 59
- 229910052799 carbon Inorganic materials 0.000 claims description 56
- 239000000460 chlorine Substances 0.000 claims description 48
- 229910052801 chlorine Inorganic materials 0.000 claims description 47
- 125000004432 carbon atom Chemical group C* 0.000 claims description 45
- 150000001875 compounds Chemical class 0.000 claims description 39
- -1 fhenyl Chemical group 0.000 claims description 38
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 37
- 239000011737 fluorine Substances 0.000 claims description 32
- 229910052731 fluorine Inorganic materials 0.000 claims description 32
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 30
- 229910052794 bromium Inorganic materials 0.000 claims description 30
- 241000238876 Acari Species 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 27
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 26
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 26
- 150000003577 thiophenes Chemical class 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 10
- 241000607479 Yersinia pestis Species 0.000 claims description 9
- 125000004970 halomethyl group Chemical group 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 5
- SDZYNDZWHGOSHW-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-phenylsulfanylthiophene Chemical compound ClC1=CC=CC(C=2SC(SC=3C=CC=CC=3)=CC=2)=C1 SDZYNDZWHGOSHW-UHFFFAOYSA-N 0.000 claims description 4
- GGJDJCBJLDHXEZ-UHFFFAOYSA-N 2-phenyl-5-phenylsulfanylthiophene Chemical compound C=1C=CC=CC=1SC(S1)=CC=C1C1=CC=CC=C1 GGJDJCBJLDHXEZ-UHFFFAOYSA-N 0.000 claims description 4
- PJRGDKFLFAYRBV-UHFFFAOYSA-N 2-phenylthiophene Chemical compound C1=CSC(C=2C=CC=CC=2)=C1 PJRGDKFLFAYRBV-UHFFFAOYSA-N 0.000 claims description 4
- USJMCEXXPYUTEE-UHFFFAOYSA-N 5-(4-fluorophenyl)-2,3-diphenylthiophene Chemical compound C1=CC(F)=CC=C1C1=CC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)S1 USJMCEXXPYUTEE-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 230000000749 insecticidal effect Effects 0.000 claims description 4
- JWXZLCFGVKMEEK-UHFFFAOYSA-N triarathene Chemical compound C1=CC(Cl)=CC=C1C1=CC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)S1 JWXZLCFGVKMEEK-UHFFFAOYSA-N 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- PITSXXFDQLCAGC-UHFFFAOYSA-N 2-(3,4-dimethylphenyl)-5-phenylsulfanylthiophene Chemical compound C1=C(C)C(C)=CC=C1C(S1)=CC=C1SC1=CC=CC=C1 PITSXXFDQLCAGC-UHFFFAOYSA-N 0.000 claims description 3
- QOYCSQBDTFMQSG-UHFFFAOYSA-N 2-(3-chlorophenyl)thiophene Chemical compound ClC1=CC=CC(C=2SC=CC=2)=C1 QOYCSQBDTFMQSG-UHFFFAOYSA-N 0.000 claims description 3
- MLSWACXFSABKQX-UHFFFAOYSA-N 2-(4-chlorophenyl)sulfanyl-5-phenylthiophene Chemical compound C1=CC(Cl)=CC=C1SC1=CC=C(C=2C=CC=CC=2)S1 MLSWACXFSABKQX-UHFFFAOYSA-N 0.000 claims description 3
- UUBWNOWUMQHZJH-UHFFFAOYSA-N 2-(4-methylphenyl)-5-phenylsulfanylthiophene Chemical compound C1=CC(C)=CC=C1C(S1)=CC=C1SC1=CC=CC=C1 UUBWNOWUMQHZJH-UHFFFAOYSA-N 0.000 claims description 3
- IIUDZDPILDMBFH-UHFFFAOYSA-N 2-(4-propan-2-ylphenyl)thiophene Chemical compound C1=CC(C(C)C)=CC=C1C1=CC=CS1 IIUDZDPILDMBFH-UHFFFAOYSA-N 0.000 claims description 3
- PETIVRQPYHAKLA-UHFFFAOYSA-N 2-[(4-methoxyphenyl)methyl]-5-phenylsulfanylthiophene Chemical compound C1=CC(OC)=CC=C1CC(S1)=CC=C1SC1=CC=CC=C1 PETIVRQPYHAKLA-UHFFFAOYSA-N 0.000 claims description 3
- WFKYHWLFRXTVOF-UHFFFAOYSA-N 2-phenylsulfanyl-5-(4-propan-2-ylphenyl)thiophene Chemical compound C1=CC(C(C)C)=CC=C1C(S1)=CC=C1SC1=CC=CC=C1 WFKYHWLFRXTVOF-UHFFFAOYSA-N 0.000 claims description 3
- VWRSEKJUUSZKSH-UHFFFAOYSA-N 3,5-diphenyl-2-phenylsulfanylthiophene Chemical compound C=1C=CC=CC=1SC=1SC(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 VWRSEKJUUSZKSH-UHFFFAOYSA-N 0.000 claims description 3
- INSDRAVBKMIDDE-UHFFFAOYSA-N 5-(2-chlorophenyl)-2,3-diphenylthiophene Chemical compound ClC1=CC=CC=C1C1=CC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)S1 INSDRAVBKMIDDE-UHFFFAOYSA-N 0.000 claims description 3
- XIZGQOHBXIBEGQ-UHFFFAOYSA-N 5-(4-methylphenyl)-2,3-diphenylthiophene Chemical compound C1=CC(C)=CC=C1C1=CC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)S1 XIZGQOHBXIBEGQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 230000003129 miticidal effect Effects 0.000 claims description 3
- QIQRZPZOOFRYRL-UHFFFAOYSA-N 2,3,5-triphenylthiophene Chemical compound C1=C(C=2C=CC=CC=2)SC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 QIQRZPZOOFRYRL-UHFFFAOYSA-N 0.000 claims description 2
- HWKZNRABKQDKTC-UHFFFAOYSA-N 2,5-diphenylthiophene Chemical compound C=1C=C(C=2C=CC=CC=2)SC=1C1=CC=CC=C1 HWKZNRABKQDKTC-UHFFFAOYSA-N 0.000 claims description 2
- AFLBPIABCXIKBD-UHFFFAOYSA-N 2-(4-methylsulfanylphenyl)thiophene Chemical compound C1=CC(SC)=CC=C1C1=CC=CS1 AFLBPIABCXIKBD-UHFFFAOYSA-N 0.000 claims description 2
- KXWVWGDIKZWGKU-UHFFFAOYSA-N 2-(benzenesulfonyl)-5-phenylthiophene Chemical compound C=1C=CC=CC=1S(=O)(=O)C(S1)=CC=C1C1=CC=CC=C1 KXWVWGDIKZWGKU-UHFFFAOYSA-N 0.000 claims description 2
- IAAKLXWAPORNCD-UHFFFAOYSA-N 5-(2,4-dimethoxyphenyl)-2,3-diphenylthiophene Chemical compound COC1=CC(OC)=CC=C1C1=CC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)S1 IAAKLXWAPORNCD-UHFFFAOYSA-N 0.000 claims description 2
- MUAUWFOFPQOSSQ-UHFFFAOYSA-N 5-(4-methoxyphenyl)-2,3-diphenylthiophene Chemical compound C1=CC(OC)=CC=C1C1=CC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)S1 MUAUWFOFPQOSSQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 10
- ORVWAOCQBJLARG-UHFFFAOYSA-N 5-(2-methoxyphenyl)-2,3-diphenylthiophene Chemical compound COC1=CC=CC=C1C1=CC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)S1 ORVWAOCQBJLARG-UHFFFAOYSA-N 0.000 claims 2
- IRNKKQWHCYLVPR-UHFFFAOYSA-N 5-(3-fluoro-4-methoxyphenyl)-2,3-diphenylthiophene Chemical compound C1=C(F)C(OC)=CC=C1C1=CC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)S1 IRNKKQWHCYLVPR-UHFFFAOYSA-N 0.000 claims 2
- RTLMTEQCQSIPLH-UHFFFAOYSA-N 5-(3-methoxyphenyl)-2,3-diphenylthiophene Chemical compound COC1=CC=CC(C=2SC(=C(C=2)C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 RTLMTEQCQSIPLH-UHFFFAOYSA-N 0.000 claims 2
- TWKDIVDAGCWHES-UHFFFAOYSA-N 2-(4-methoxyphenyl)thiophene Chemical compound C1=CC(OC)=CC=C1C1=CC=CS1 TWKDIVDAGCWHES-UHFFFAOYSA-N 0.000 claims 1
- YRKAJCGUTWECCT-UHFFFAOYSA-N 2-(4-nitrophenyl)thiophene Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=CC=CS1 YRKAJCGUTWECCT-UHFFFAOYSA-N 0.000 claims 1
- YKTPNHVEYBMYLV-UHFFFAOYSA-N 2-bromo-3,5-diphenylthiophene Chemical compound BrC=1SC(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 YKTPNHVEYBMYLV-UHFFFAOYSA-N 0.000 claims 1
- SGVIUSGVQLERSF-UHFFFAOYSA-N 5-(4-tert-butylphenyl)-2,3-diphenylthiophene Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=CC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)S1 SGVIUSGVQLERSF-UHFFFAOYSA-N 0.000 claims 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 53
- 229910052717 sulfur Inorganic materials 0.000 description 47
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 31
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 30
- 238000004458 analytical method Methods 0.000 description 29
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 29
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 23
- 239000000243 solution Substances 0.000 description 21
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 238000001953 recrystallisation Methods 0.000 description 15
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- SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 125000002078 anthracen-1-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([*])=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 235000021016 apples Nutrition 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- NOSOEJSZWOKISI-UHFFFAOYSA-N butane-1,4-dione Chemical compound O=[C]CC[C]=O NOSOEJSZWOKISI-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 238000009838 combustion analysis Methods 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 244000221110 common millet Species 0.000 description 1
- 229940125846 compound 25 Drugs 0.000 description 1
- 229940125851 compound 27 Drugs 0.000 description 1
- 229940127204 compound 29 Drugs 0.000 description 1
- 229940125877 compound 31 Drugs 0.000 description 1
- 229940125878 compound 36 Drugs 0.000 description 1
- 229940125807 compound 37 Drugs 0.000 description 1
- 229940127573 compound 38 Drugs 0.000 description 1
- 229940126540 compound 41 Drugs 0.000 description 1
- 229940125936 compound 42 Drugs 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229940082150 encore Drugs 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 1
- QVDYYQXUNAQSNI-UHFFFAOYSA-N ethyl acetate;pentane Chemical compound CCCCC.CCOC(C)=O QVDYYQXUNAQSNI-UHFFFAOYSA-N 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000021021 grapes Nutrition 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
- 239000008263 liquid aerosol Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 201000002266 mite infestation Diseases 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- UYDLBVPAAFVANX-UHFFFAOYSA-N octylphenoxy polyethoxyethanol Chemical compound CC(C)(C)CC(C)(C)C1=CC=C(OCCOCCOCCOCCO)C=C1 UYDLBVPAAFVANX-UHFFFAOYSA-N 0.000 description 1
- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 208000007865 relapsing fever Diseases 0.000 description 1
- 230000037380 skin damage Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 125000003375 sulfoxide group Chemical group 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000013022 venting Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/28—Halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/08—Hydrogen atoms or radicals containing only hydrogen and carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/12—Radicals substituted by halogen atoms or nitro or nitroso radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/18—Radicals substituted by singly bound hetero atoms other than halogen by sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/34—Sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US69166076A | 1976-06-01 | 1976-06-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2724494A1 true DE2724494A1 (de) | 1977-12-08 |
Family
ID=24777438
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772724494 Pending DE2724494A1 (de) | 1976-06-01 | 1977-05-31 | Verfahren zur kontrolle von milben- und insekten-schaedlingen, milben- und insektenbekaempfungsmittel und substituierte thiophene |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS52148067A (enExample) |
| CA (1) | CA1086643A (enExample) |
| DE (1) | DE2724494A1 (enExample) |
| FR (1) | FR2353228A1 (enExample) |
| NL (1) | NL7706027A (enExample) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4426524A (en) | 1980-09-02 | 1984-01-17 | Fmc Corporation | Heterocyclic substituted benzyl alcohol, insecticidal ester derivatives, and intermediates |
| US4999436A (en) * | 1987-09-22 | 1991-03-12 | Merck & Co., Inc. | Aryl-substituted thiophene 3-ols, derivatives and analogs useful as lipoxgenase inhibitors |
| EP1982594A1 (de) | 2003-11-14 | 2008-10-22 | Bayer CropScience AG | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| DE102007045922A1 (de) | 2007-09-26 | 2009-04-02 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| EP2127522A1 (de) | 2008-05-29 | 2009-12-02 | Bayer CropScience AG | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| EP2382865A1 (de) | 2010-04-28 | 2011-11-02 | Bayer CropScience AG | Synergistische Wirkstoffkombinationen |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ211146A (en) * | 1984-02-29 | 1987-10-30 | Merck & Co Inc | 2,5-diaryl-tetrahydrothiophene derivatives and pharmaceutical compositions |
-
1977
- 1977-01-14 CA CA269,731A patent/CA1086643A/en not_active Expired
- 1977-05-27 FR FR7716377A patent/FR2353228A1/fr not_active Withdrawn
- 1977-05-31 JP JP6291877A patent/JPS52148067A/ja active Granted
- 1977-05-31 DE DE19772724494 patent/DE2724494A1/de active Pending
- 1977-06-01 NL NL7706027A patent/NL7706027A/xx not_active Application Discontinuation
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4426524A (en) | 1980-09-02 | 1984-01-17 | Fmc Corporation | Heterocyclic substituted benzyl alcohol, insecticidal ester derivatives, and intermediates |
| US4999436A (en) * | 1987-09-22 | 1991-03-12 | Merck & Co., Inc. | Aryl-substituted thiophene 3-ols, derivatives and analogs useful as lipoxgenase inhibitors |
| EP1982594A1 (de) | 2003-11-14 | 2008-10-22 | Bayer CropScience AG | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| DE102007045922A1 (de) | 2007-09-26 | 2009-04-02 | Bayer Cropscience Ag | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| EP2127522A1 (de) | 2008-05-29 | 2009-12-02 | Bayer CropScience AG | Wirkstoffkombinationen mit insektiziden und akariziden Eigenschaften |
| EP2382865A1 (de) | 2010-04-28 | 2011-11-02 | Bayer CropScience AG | Synergistische Wirkstoffkombinationen |
| WO2011134964A1 (de) | 2010-04-28 | 2011-11-03 | Bayer Cropscience Ag | Synergistische wirkstoffkombinationen |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS52148067A (en) | 1977-12-08 |
| NL7706027A (nl) | 1977-12-05 |
| CA1086643A (en) | 1980-09-30 |
| FR2353228A1 (fr) | 1977-12-30 |
| JPS558506B2 (enExample) | 1980-03-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| OHW | Rejection |