SK689989A3 - Pyrrole derivatives, insecticidal and acaricidal agent containing same and their use - Google Patents
Pyrrole derivatives, insecticidal and acaricidal agent containing same and their use Download PDFInfo
- Publication number
- SK689989A3 SK689989A3 SK6899-89A SK689989A SK689989A3 SK 689989 A3 SK689989 A3 SK 689989A3 SK 689989 A SK689989 A SK 689989A SK 689989 A3 SK689989 A3 SK 689989A3
- Authority
- SK
- Slovakia
- Prior art keywords
- cyano
- pyrrole
- dichloro
- trifluoromethylphenyl
- chloro
- Prior art date
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- 150000003233 pyrroles Chemical class 0.000 title claims description 16
- 230000000895 acaricidal effect Effects 0.000 title claims description 9
- 230000000749 insecticidal effect Effects 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 186
- 239000000203 mixture Substances 0.000 claims description 100
- -1 1- (2,6-dichloro-4-trifluoromethylphenyl) -2-chloro-3-cyano-4-trifluoromethylsulfinyl-5-bromopyridine Chemical compound 0.000 claims description 60
- 239000000460 chlorine Substances 0.000 claims description 60
- 229910052739 hydrogen Inorganic materials 0.000 claims description 46
- 239000001257 hydrogen Substances 0.000 claims description 46
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 44
- 239000004480 active ingredient Substances 0.000 claims description 40
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 39
- 125000005843 halogen group Chemical group 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 125000001188 haloalkyl group Chemical group 0.000 claims description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
- 125000004414 alkyl thio group Chemical group 0.000 claims description 24
- 229910052801 chlorine Inorganic materials 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 241000238876 Acari Species 0.000 claims description 11
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 241000238631 Hexapoda Species 0.000 claims description 9
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
- 125000004995 haloalkylthio group Chemical group 0.000 claims description 8
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 claims description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 7
- 150000003254 radicals Chemical group 0.000 claims description 7
- PJKWHQWDOVRAPZ-UHFFFAOYSA-N 2-chloro-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfanyl)pyrrole-3-carbonitrile Chemical compound ClC1=C(C#N)C(SC(F)(F)F)=CN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl PJKWHQWDOVRAPZ-UHFFFAOYSA-N 0.000 claims description 6
- JIPKGZGRXPPXLO-UHFFFAOYSA-N 5-amino-2-chloro-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfanyl)pyrrole-3-carbonitrile Chemical compound NC1=C(SC(F)(F)F)C(C#N)=C(Cl)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl JIPKGZGRXPPXLO-UHFFFAOYSA-N 0.000 claims description 6
- 239000000969 carrier Substances 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- QYCLVBVJUKKXIY-UHFFFAOYSA-N 2-chloro-1-[2,6-dichloro-4-(trifluoromethoxy)phenyl]-4-(trifluoromethylsulfonyl)pyrrole-3-carbonitrile Chemical compound ClC1=CC(OC(F)(F)F)=CC(Cl)=C1N1C(Cl)=C(C#N)C(S(=O)(=O)C(F)(F)F)=C1 QYCLVBVJUKKXIY-UHFFFAOYSA-N 0.000 claims description 5
- QLAACFJZZMUARS-UHFFFAOYSA-N 2-chloro-4-[dichloro(fluoro)methyl]sulfanyl-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrrole-3-carbonitrile Chemical compound ClC1=C(C#N)C(SC(Cl)(Cl)F)=CN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl QLAACFJZZMUARS-UHFFFAOYSA-N 0.000 claims description 5
- CADPGIHCCXXPHI-UHFFFAOYSA-N 2-chloro-4-[dichloro(fluoro)methyl]sulfinyl-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrrole-3-carbonitrile Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1N1C(Cl)=C(C#N)C(S(=O)C(F)(Cl)Cl)=C1 CADPGIHCCXXPHI-UHFFFAOYSA-N 0.000 claims description 5
- OSERJKSIBWTOSC-UHFFFAOYSA-N 2-chloro-4-[dichloro(fluoro)methyl]sulfonyl-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrrole-3-carbonitrile Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1N1C(Cl)=C(C#N)C(S(=O)(=O)C(F)(Cl)Cl)=C1 OSERJKSIBWTOSC-UHFFFAOYSA-N 0.000 claims description 5
- ACHOLDMXYSODSW-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfanyl)pyrrole-3-carbonitrile Chemical compound NC1=C(SC(F)(F)F)C(C#N)=CN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ACHOLDMXYSODSW-UHFFFAOYSA-N 0.000 claims description 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
- FMBQMSRBKHSQLL-UHFFFAOYSA-N 5-amino-2-bromo-1-[2-chloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfanyl)pyrrole-3-carbonitrile Chemical compound NC1=C(SC(F)(F)F)C(C#N)=C(Br)N1C1=CC=C(C(F)(F)F)C=C1Cl FMBQMSRBKHSQLL-UHFFFAOYSA-N 0.000 claims description 4
- VSSIBQTWYRAYCR-UHFFFAOYSA-N 5-bromo-2-chloro-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfanyl)pyrrole-3-carbonitrile Chemical compound ClC1=C(C#N)C(SC(F)(F)F)=C(Br)N1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl VSSIBQTWYRAYCR-UHFFFAOYSA-N 0.000 claims description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- HFEOIQVXKRFABN-UHFFFAOYSA-N 1-(2,4,6-trichlorophenyl)-4-(trifluoromethylsulfanyl)pyrrole-3-carbonitrile Chemical compound C1=C(C#N)C(SC(F)(F)F)=CN1C1=C(Cl)C=C(Cl)C=C1Cl HFEOIQVXKRFABN-UHFFFAOYSA-N 0.000 claims description 3
- ONQZIPAGVIWZKM-UHFFFAOYSA-N 2-chloro-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfinyl)pyrrole-3-carbonitrile Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1N1C(Cl)=C(C#N)C(S(=O)C(F)(F)F)=C1 ONQZIPAGVIWZKM-UHFFFAOYSA-N 0.000 claims description 3
- CQSBJLMSDCJYGB-UHFFFAOYSA-N 4-[dichloro(fluoro)methyl]sulfinyl-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrrole-3-carbonitrile Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1N1C=C(S(=O)C(F)(Cl)Cl)C(C#N)=C1 CQSBJLMSDCJYGB-UHFFFAOYSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 3
- 125000005221 halo alkyl carbonyl amino group Chemical group 0.000 claims description 3
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- IRZUMURIODGTLE-UHFFFAOYSA-N 1-(2,4,6-trichlorophenyl)-4-(trifluoromethylsulfonyl)pyrrole-3-carbonitrile Chemical compound C1=C(C#N)C(S(=O)(=O)C(F)(F)F)=CN1C1=C(Cl)C=C(Cl)C=C1Cl IRZUMURIODGTLE-UHFFFAOYSA-N 0.000 claims description 2
- FXABPQDICWREHN-UHFFFAOYSA-N 1-(4-bromo-2,6-dichlorophenyl)-4-(trifluoromethylsulfanyl)pyrrole-3-carbonitrile Chemical compound C1=C(C#N)C(SC(F)(F)F)=CN1C1=C(Cl)C=C(Br)C=C1Cl FXABPQDICWREHN-UHFFFAOYSA-N 0.000 claims description 2
- ITVDBXOTSCPCCO-UHFFFAOYSA-N 1-(4-bromo-2,6-dichlorophenyl)-4-(trifluoromethylsulfinyl)pyrrole-3-carbonitrile Chemical compound C1=C(C#N)C(S(=O)C(F)(F)F)=CN1C1=C(Cl)C=C(Br)C=C1Cl ITVDBXOTSCPCCO-UHFFFAOYSA-N 0.000 claims description 2
- DMWUUYVFRKEESO-UHFFFAOYSA-N 1-(4-bromo-2,6-dichlorophenyl)-4-(trifluoromethylsulfonyl)pyrrole-3-carbonitrile Chemical compound C1=C(C#N)C(S(=O)(=O)C(F)(F)F)=CN1C1=C(Cl)C=C(Br)C=C1Cl DMWUUYVFRKEESO-UHFFFAOYSA-N 0.000 claims description 2
- JYOGOEWOJDMCQJ-UHFFFAOYSA-N 1-(4-bromo-2,6-dichlorophenyl)-4-[chloro(difluoro)methyl]sulfanylpyrrole-3-carbonitrile Chemical compound C1=C(C#N)C(SC(F)(Cl)F)=CN1C1=C(Cl)C=C(Br)C=C1Cl JYOGOEWOJDMCQJ-UHFFFAOYSA-N 0.000 claims description 2
- KHSCRRNSQRLQND-UHFFFAOYSA-N 1-(4-bromo-2,6-dichlorophenyl)-4-[chloro(difluoro)methyl]sulfinylpyrrole-3-carbonitrile Chemical compound C1=C(C#N)C(S(=O)C(F)(Cl)F)=CN1C1=C(Cl)C=C(Br)C=C1Cl KHSCRRNSQRLQND-UHFFFAOYSA-N 0.000 claims description 2
- UQGOHGJWBFNKCA-UHFFFAOYSA-N 1-(4-bromo-2,6-dichlorophenyl)-4-[chloro(difluoro)methyl]sulfonylpyrrole-3-carbonitrile Chemical compound C1=C(C#N)C(S(=O)(=O)C(F)(Cl)F)=CN1C1=C(Cl)C=C(Br)C=C1Cl UQGOHGJWBFNKCA-UHFFFAOYSA-N 0.000 claims description 2
- DPRSXIXKIYNLAQ-UHFFFAOYSA-N 1-(4-bromo-2,6-dichlorophenyl)-4-[dichloro(fluoro)methyl]sulfanylpyrrole-3-carbonitrile Chemical compound C1=C(C#N)C(SC(Cl)(Cl)F)=CN1C1=C(Cl)C=C(Br)C=C1Cl DPRSXIXKIYNLAQ-UHFFFAOYSA-N 0.000 claims description 2
- SAQMKOCIZRQLLJ-UHFFFAOYSA-N 1-(4-bromo-2,6-dichlorophenyl)-4-[dichloro(fluoro)methyl]sulfinylpyrrole-3-carbonitrile Chemical compound C1=C(C#N)C(S(=O)C(Cl)(Cl)F)=CN1C1=C(Cl)C=C(Br)C=C1Cl SAQMKOCIZRQLLJ-UHFFFAOYSA-N 0.000 claims description 2
- DGPCTVKLPVZZFI-UHFFFAOYSA-N 1-(4-bromo-2,6-dichlorophenyl)-4-[dichloro(fluoro)methyl]sulfonylpyrrole-3-carbonitrile Chemical compound C1=C(C#N)C(S(=O)(=O)C(Cl)(Cl)F)=CN1C1=C(Cl)C=C(Br)C=C1Cl DGPCTVKLPVZZFI-UHFFFAOYSA-N 0.000 claims description 2
- MOOQSNAQQORCPW-UHFFFAOYSA-N 1-(4-bromo-2,6-difluorophenyl)-4-[dichloro(fluoro)methyl]sulfanylpyrrole-3-carbonitrile Chemical compound FC1=CC(Br)=CC(F)=C1N1C=C(C#N)C(SC(F)(Cl)Cl)=C1 MOOQSNAQQORCPW-UHFFFAOYSA-N 0.000 claims description 2
- FKGMIKRTCPDHHX-UHFFFAOYSA-N 1-(4-bromo-2,6-dimethylphenyl)-4-(trifluoromethylsulfinyl)pyrrole-3-carbonitrile Chemical compound CC1=CC(Br)=CC(C)=C1N1C=C(S(=O)C(F)(F)F)C(C#N)=C1 FKGMIKRTCPDHHX-UHFFFAOYSA-N 0.000 claims description 2
- XCSJAMJIXBQZPY-UHFFFAOYSA-N 2-bromo-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfinyl)pyrrole-3-carbonitrile Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1N1C(Br)=C(C#N)C(S(=O)C(F)(F)F)=C1 XCSJAMJIXBQZPY-UHFFFAOYSA-N 0.000 claims description 2
- ISZDMLAVSPUZBG-UHFFFAOYSA-N 2-bromo-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfonyl)pyrrole-3-carbonitrile Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1N1C(Br)=C(C#N)C(S(=O)(=O)C(F)(F)F)=C1 ISZDMLAVSPUZBG-UHFFFAOYSA-N 0.000 claims description 2
- QNDCDGBKNFAILD-UHFFFAOYSA-N 2-bromo-1-[2-chloro-4-(trifluoromethyl)phenyl]-4-[dichloro(fluoro)methyl]sulfonylpyrrole-3-carbonitrile Chemical compound ClC1=CC(C(F)(F)F)=CC=C1N1C(Br)=C(C#N)C(S(=O)(=O)C(F)(Cl)Cl)=C1 QNDCDGBKNFAILD-UHFFFAOYSA-N 0.000 claims description 2
- YLMWNNUKXDGGEM-UHFFFAOYSA-N 2-bromo-4-[chloro(difluoro)methyl]sulfanyl-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrrole-3-carbonitrile Chemical compound BrC1=C(C#N)C(SC(F)(Cl)F)=CN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl YLMWNNUKXDGGEM-UHFFFAOYSA-N 0.000 claims description 2
- IRPGWLUXEMYNDY-UHFFFAOYSA-N 2-bromo-4-[chloro(difluoro)methyl]sulfinyl-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrrole-3-carbonitrile Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1N1C(Br)=C(C#N)C(S(=O)C(F)(F)Cl)=C1 IRPGWLUXEMYNDY-UHFFFAOYSA-N 0.000 claims description 2
- JPYXNPMKDKSRDL-UHFFFAOYSA-N 2-bromo-4-[chloro(difluoro)methyl]sulfonyl-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrrole-3-carbonitrile Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1N1C(Br)=C(C#N)C(S(=O)(=O)C(F)(F)Cl)=C1 JPYXNPMKDKSRDL-UHFFFAOYSA-N 0.000 claims description 2
- RPSKDKFJRIANLI-UHFFFAOYSA-N 2-bromo-4-[dichloro(fluoro)methyl]sulfanyl-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrrole-3-carbonitrile Chemical compound BrC1=C(C#N)C(SC(Cl)(Cl)F)=CN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl RPSKDKFJRIANLI-UHFFFAOYSA-N 0.000 claims description 2
- AMRNWPPZEPFZCK-UHFFFAOYSA-N 2-bromo-4-[dichloro(fluoro)methyl]sulfinyl-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrrole-3-carbonitrile Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1N1C(Br)=C(C#N)C(S(=O)C(F)(Cl)Cl)=C1 AMRNWPPZEPFZCK-UHFFFAOYSA-N 0.000 claims description 2
- BLOCOLOABOHNMO-UHFFFAOYSA-N 2-bromo-4-[dichloro(fluoro)methyl]sulfonyl-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrrole-3-carbonitrile Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1N1C(Br)=C(C#N)C(S(=O)(=O)C(F)(Cl)Cl)=C1 BLOCOLOABOHNMO-UHFFFAOYSA-N 0.000 claims description 2
- YGYPMNSFMKEKCN-UHFFFAOYSA-N 2-chloro-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfonyl)pyrrole-3-carbonitrile Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1N1C(Cl)=C(C#N)C(S(=O)(=O)C(F)(F)F)=C1 YGYPMNSFMKEKCN-UHFFFAOYSA-N 0.000 claims description 2
- SSWFEYFQVDHGBZ-UHFFFAOYSA-N 2-chloro-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfinylpyrrole-3-carbonitrile Chemical compound ClC1=C(C#N)C(S(=O)C)=CN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl SSWFEYFQVDHGBZ-UHFFFAOYSA-N 0.000 claims description 2
- VWZMIXHSXRWQLL-UHFFFAOYSA-N 2-chloro-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylsulfonylpyrrole-3-carbonitrile Chemical compound ClC1=C(C#N)C(S(=O)(=O)C)=CN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl VWZMIXHSXRWQLL-UHFFFAOYSA-N 0.000 claims description 2
- LJQVFYZTUYZPON-UHFFFAOYSA-N 2-chloro-1-[2-chloro-4-(trifluoromethyl)phenyl]-4-[dichloro(fluoro)methyl]sulfinylpyrrole-3-carbonitrile Chemical compound ClC1=CC(C(F)(F)F)=CC=C1N1C(Cl)=C(C#N)C(S(=O)C(F)(Cl)Cl)=C1 LJQVFYZTUYZPON-UHFFFAOYSA-N 0.000 claims description 2
- DMEHQJYQLGKSMP-UHFFFAOYSA-N 2-chloro-1-[2-chloro-4-(trifluoromethyl)phenyl]-4-[dichloro(fluoro)methyl]sulfonylpyrrole-3-carbonitrile Chemical compound ClC1=CC(C(F)(F)F)=CC=C1N1C(Cl)=C(C#N)C(S(=O)(=O)C(F)(Cl)Cl)=C1 DMEHQJYQLGKSMP-UHFFFAOYSA-N 0.000 claims description 2
- YKPWWHBRKSYWMY-UHFFFAOYSA-N 2-chloro-4-[chloro(difluoro)methyl]sulfanyl-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrrole-3-carbonitrile Chemical compound ClC1=C(C#N)C(SC(F)(Cl)F)=CN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl YKPWWHBRKSYWMY-UHFFFAOYSA-N 0.000 claims description 2
- QKLWHGSXKIXESL-UHFFFAOYSA-N 2-chloro-4-[chloro(difluoro)methyl]sulfinyl-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrrole-3-carbonitrile Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1N1C(Cl)=C(C#N)C(S(=O)C(F)(F)Cl)=C1 QKLWHGSXKIXESL-UHFFFAOYSA-N 0.000 claims description 2
- YXKAUSUBHLVBPH-UHFFFAOYSA-N 2-chloro-4-[chloro(difluoro)methyl]sulfonyl-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrrole-3-carbonitrile Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1N1C(Cl)=C(C#N)C(S(=O)(=O)C(F)(F)Cl)=C1 YXKAUSUBHLVBPH-UHFFFAOYSA-N 0.000 claims description 2
- XKLQOCIWJHNCFX-UHFFFAOYSA-N 2-chloro-4-[dichloro(fluoro)methyl]sulfinyl-1-[2,6-dichloro-4-(trifluoromethoxy)phenyl]pyrrole-3-carbonitrile Chemical compound ClC1=CC(OC(F)(F)F)=CC(Cl)=C1N1C(Cl)=C(C#N)C(S(=O)C(F)(Cl)Cl)=C1 XKLQOCIWJHNCFX-UHFFFAOYSA-N 0.000 claims description 2
- DXCPGBMMFHWPOK-UHFFFAOYSA-N 2-chloro-4-[dichloro(fluoro)methyl]sulfonyl-1-[2,6-dichloro-4-(trifluoromethoxy)phenyl]pyrrole-3-carbonitrile Chemical compound ClC1=CC(OC(F)(F)F)=CC(Cl)=C1N1C(Cl)=C(C#N)C(S(=O)(=O)C(F)(Cl)Cl)=C1 DXCPGBMMFHWPOK-UHFFFAOYSA-N 0.000 claims description 2
- QTKBHQMSQVIOAS-UHFFFAOYSA-N 4-[bromo(difluoro)methyl]sulfanyl-2-chloro-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrrole-3-carbonitrile Chemical compound ClC1=C(C#N)C(SC(F)(Br)F)=CN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl QTKBHQMSQVIOAS-UHFFFAOYSA-N 0.000 claims description 2
- YWQRLLSDLDQKLH-UHFFFAOYSA-N 4-[bromo(difluoro)methyl]sulfonyl-2-chloro-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrrole-3-carbonitrile Chemical compound ClC1=CC(C(F)(F)F)=CC(Cl)=C1N1C(Cl)=C(C#N)C(S(=O)(=O)C(F)(F)Br)=C1 YWQRLLSDLDQKLH-UHFFFAOYSA-N 0.000 claims description 2
- FWRYVUABAYJMGK-UHFFFAOYSA-N 4-[chloro(difluoro)methyl]sulfanyl-1-(2,4,6-trichlorophenyl)pyrrole-3-carbonitrile Chemical compound C1=C(C#N)C(SC(F)(Cl)F)=CN1C1=C(Cl)C=C(Cl)C=C1Cl FWRYVUABAYJMGK-UHFFFAOYSA-N 0.000 claims description 2
- QGVHLIYLGRLUOH-UHFFFAOYSA-N 4-[chloro(difluoro)methyl]sulfinyl-1-(2,4,6-trichlorophenyl)pyrrole-3-carbonitrile Chemical compound C1=C(C#N)C(S(=O)C(F)(Cl)F)=CN1C1=C(Cl)C=C(Cl)C=C1Cl QGVHLIYLGRLUOH-UHFFFAOYSA-N 0.000 claims description 2
- WBPBHDOLOXJMKB-UHFFFAOYSA-N 4-[chloro(difluoro)methyl]sulfonyl-1-(2,4,6-trichlorophenyl)pyrrole-3-carbonitrile Chemical compound C1=C(C#N)C(S(=O)(=O)C(F)(Cl)F)=CN1C1=C(Cl)C=C(Cl)C=C1Cl WBPBHDOLOXJMKB-UHFFFAOYSA-N 0.000 claims description 2
- UOPABXCHHSZFJX-UHFFFAOYSA-N 4-[dichloro(fluoro)methyl]sulfanyl-1-(2,4,6-trichlorophenyl)pyrrole-3-carbonitrile Chemical compound C1=C(C#N)C(SC(Cl)(Cl)F)=CN1C1=C(Cl)C=C(Cl)C=C1Cl UOPABXCHHSZFJX-UHFFFAOYSA-N 0.000 claims description 2
- INMKNEVRKGLNPQ-UHFFFAOYSA-N 4-[dichloro(fluoro)methyl]sulfanyl-1-(2,6-dichlorophenyl)pyrrole-3-carbonitrile Chemical compound C1=C(C#N)C(SC(Cl)(Cl)F)=CN1C1=C(Cl)C=CC=C1Cl INMKNEVRKGLNPQ-UHFFFAOYSA-N 0.000 claims description 2
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- YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 0.000 description 1
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
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- YFMZQCCTZUJXEB-UHFFFAOYSA-N tris(methylsulfanyl)methane Chemical compound CSC(SC)SC YFMZQCCTZUJXEB-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members 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
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Pyrrole Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28243988A | 1988-12-09 | 1988-12-09 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK278926B6 SK278926B6 (sk) | 1998-04-08 |
| SK689989A3 true SK689989A3 (en) | 1998-04-08 |
Family
ID=23081529
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK6899-89A SK689989A3 (en) | 1988-12-09 | 1989-12-06 | Pyrrole derivatives, insecticidal and acaricidal agent containing same and their use |
Country Status (21)
| Country | Link |
|---|---|
| CN (1) | CN1028475C (he) |
| BG (1) | BG60842B1 (he) |
| CZ (1) | CZ284089B6 (he) |
| DD (1) | DD289920A5 (he) |
| DK (1) | DK175618B1 (he) |
| EG (1) | EG19169A (he) |
| FI (1) | FI95462C (he) |
| IL (1) | IL92507A (he) |
| MA (1) | MA21689A1 (he) |
| MX (1) | MX18585A (he) |
| MY (1) | MY105867A (he) |
| NO (1) | NO174344C (he) |
| OA (1) | OA09248A (he) |
| PL (1) | PL162669B1 (he) |
| PT (1) | PT92521B (he) |
| RO (1) | RO105644B1 (he) |
| RU (1) | RU2063688C1 (he) |
| SK (1) | SK689989A3 (he) |
| TR (1) | TR25800A (he) |
| UA (1) | UA37172C2 (he) |
| ZA (1) | ZA899418B (he) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL98235A (en) * | 1990-07-31 | 1999-07-14 | American Cyanamid Co | Process for the preparation of insecticidal acaridical and nematicidal 2-aryl-5-(trifluoromethyl) pyrrole compounds and intermediates thereof |
| JP2012082186A (ja) * | 2010-09-15 | 2012-04-26 | Bayer Cropscience Ag | 殺虫性アリールピロリジン類 |
| CN104418789A (zh) * | 2013-08-26 | 2015-03-18 | 南开大学 | 对氯苄基吡咯类化合物及其制备和在防治虫螨菌方面的应用 |
-
1989
- 1989-11-30 IL IL9250789A patent/IL92507A/he not_active IP Right Cessation
- 1989-12-03 EG EG59489A patent/EG19169A/xx active
- 1989-12-04 MY MYPI89001691A patent/MY105867A/en unknown
- 1989-12-05 MX MX1858589A patent/MX18585A/es unknown
- 1989-12-05 MA MA21947A patent/MA21689A1/fr unknown
- 1989-12-06 SK SK6899-89A patent/SK689989A3/sk unknown
- 1989-12-06 CZ CS896899A patent/CZ284089B6/cs not_active IP Right Cessation
- 1989-12-07 NO NO894905A patent/NO174344C/no not_active IP Right Cessation
- 1989-12-07 PT PT92521A patent/PT92521B/pt not_active IP Right Cessation
- 1989-12-08 FI FI895886A patent/FI95462C/fi active IP Right Grant
- 1989-12-08 DD DD89335423A patent/DD289920A5/de not_active IP Right Cessation
- 1989-12-08 TR TR89/1040A patent/TR25800A/xx unknown
- 1989-12-08 UA UA4742713A patent/UA37172C2/uk unknown
- 1989-12-08 ZA ZA899418A patent/ZA899418B/xx unknown
- 1989-12-08 BG BG90609A patent/BG60842B1/bg unknown
- 1989-12-08 PL PL28268589A patent/PL162669B1/pl unknown
- 1989-12-08 OA OA59693A patent/OA09248A/xx unknown
- 1989-12-08 DK DK198906203A patent/DK175618B1/da not_active IP Right Cessation
- 1989-12-08 RU SU894742713A patent/RU2063688C1/ru not_active IP Right Cessation
- 1989-12-09 RO RO143072A patent/RO105644B1/ro unknown
- 1989-12-09 CN CN89108985A patent/CN1028475C/zh not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FI95462B (fi) | 1995-10-31 |
| EG19169A (en) | 1994-07-30 |
| UA37172C2 (uk) | 2001-05-15 |
| IL92507A0 (en) | 1990-08-31 |
| RO105644B1 (ro) | 1992-11-30 |
| MY105867A (en) | 1995-02-28 |
| DK620389A (da) | 1990-06-10 |
| IL92507A (he) | 1994-06-24 |
| TR25800A (tr) | 1993-08-06 |
| FI895886A0 (fi) | 1989-12-08 |
| DD289920A5 (de) | 1991-05-16 |
| CN1028475C (zh) | 1995-05-24 |
| OA09248A (en) | 1992-06-30 |
| CZ689989A3 (cs) | 1998-05-13 |
| MA21689A1 (fr) | 1990-07-01 |
| PT92521B (pt) | 1997-01-31 |
| PL162669B1 (pl) | 1993-12-31 |
| NO894905D0 (no) | 1989-12-07 |
| SK278926B6 (sk) | 1998-04-08 |
| CZ284089B6 (cs) | 1998-08-12 |
| NO894905L (no) | 1990-06-11 |
| BG90609A (bg) | 1993-12-24 |
| CN1043500A (zh) | 1990-07-04 |
| MX18585A (es) | 1994-02-28 |
| DK175618B1 (da) | 2004-12-27 |
| RU2063688C1 (ru) | 1996-07-20 |
| ZA899418B (en) | 1990-10-31 |
| NO174344C (no) | 1994-04-20 |
| DK620389D0 (da) | 1989-12-08 |
| BG60842B1 (bg) | 1996-05-31 |
| FI95462C (fi) | 1996-02-12 |
| NO174344B (no) | 1994-01-10 |
| PT92521A (pt) | 1990-06-29 |
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