IL99209A - Bis-and tris (trifluoromethyl) arylpyrroles process for their preparation and insecticidal and acaricidal compositions containing them - Google Patents
Bis-and tris (trifluoromethyl) arylpyrroles process for their preparation and insecticidal and acaricidal compositions containing themInfo
- Publication number
- IL99209A IL99209A IL9920991A IL9920991A IL99209A IL 99209 A IL99209 A IL 99209A IL 9920991 A IL9920991 A IL 9920991A IL 9920991 A IL9920991 A IL 9920991A IL 99209 A IL99209 A IL 99209A
- Authority
- IL
- Israel
- Prior art keywords
- bis
- halogen atoms
- optionally substituted
- trifluoromethyl
- alkyl
- Prior art date
Links
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 title claims abstract description 77
- 239000007983 Tris buffer Substances 0.000 title claims abstract description 38
- 238000002360 preparation method Methods 0.000 title claims abstract description 29
- 238000000034 method Methods 0.000 title claims abstract description 18
- 239000000203 mixture Substances 0.000 title claims description 23
- 230000000895 acaricidal effect Effects 0.000 title abstract description 12
- 230000000749 insecticidal effect Effects 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 66
- 241000238631 Hexapoda Species 0.000 claims abstract description 12
- 125000005843 halogen group Chemical group 0.000 claims description 95
- 125000000217 alkyl group Chemical group 0.000 claims description 63
- 125000003545 alkoxy group Chemical group 0.000 claims description 58
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 44
- -1 one C.-C Chemical group 0.000 claims description 39
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
- 229910052794 bromium Inorganic materials 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 229910052731 fluorine Inorganic materials 0.000 claims description 23
- 239000002904 solvent Substances 0.000 claims description 21
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 17
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 14
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 14
- 241000238876 Acari Species 0.000 claims description 12
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 12
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 12
- 229910052740 iodine Inorganic materials 0.000 claims description 12
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
- JHNRZXQVBKRYKN-VQHVLOKHSA-N (ne)-n-(1-phenylethylidene)hydroxylamine Chemical compound O\N=C(/C)C1=CC=CC=C1 JHNRZXQVBKRYKN-VQHVLOKHSA-N 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 8
- 125000005193 alkenylcarbonyloxy group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 239000002689 soil Substances 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- WBCLXFIDEDJGCC-UHFFFAOYSA-N hexafluoro-2-butyne Chemical compound FC(F)(F)C#CC(F)(F)F WBCLXFIDEDJGCC-UHFFFAOYSA-N 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
- 229920002554 vinyl polymer Polymers 0.000 claims description 7
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 6
- 230000002140 halogenating effect Effects 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 5
- FHUDAMLDXFJHJE-UHFFFAOYSA-N 1,1,1-trifluoropropan-2-one Chemical compound CC(=O)C(F)(F)F FHUDAMLDXFJHJE-UHFFFAOYSA-N 0.000 claims description 4
- MHNKBFPGHOSXJS-UHFFFAOYSA-N 5-(trifluoromethyl)-3,4-dihydro-2H-pyrrol-2-ol Chemical compound FC(F)(F)C1=NC(CC1)O MHNKBFPGHOSXJS-UHFFFAOYSA-N 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 235000013305 food Nutrition 0.000 claims description 4
- JJPSNVRYEOHSAD-UHFFFAOYSA-N 2,3-dichloro-1,1,3,4,4,4-hexafluorobut-1-ene Chemical compound FC(F)=C(Cl)C(F)(Cl)C(F)(F)F JJPSNVRYEOHSAD-UHFFFAOYSA-N 0.000 claims description 3
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 3
- YAXXJPKGNGKJGZ-UHFFFAOYSA-N 5-(trifluoromethyl)-3,4-dihydro-2h-pyrrol-3-ol Chemical compound OC1CN=C(C(F)(F)F)C1 YAXXJPKGNGKJGZ-UHFFFAOYSA-N 0.000 claims description 3
- SUHPVIWAYJQMBD-UHFFFAOYSA-N [C].N1C=CC=C1 Chemical group [C].N1C=CC=C1 SUHPVIWAYJQMBD-UHFFFAOYSA-N 0.000 claims description 3
- 238000009395 breeding Methods 0.000 claims description 3
- 230000001488 breeding effect Effects 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 2
- QZCOCZZLSRYRMD-UHFFFAOYSA-N 2-(trifluoromethyl)pyrrole-1-carbonitrile Chemical compound FC(F)(F)C1=CC=CN1C#N QZCOCZZLSRYRMD-UHFFFAOYSA-N 0.000 claims description 2
- CXIBBZMZNFNDNH-UHFFFAOYSA-N 3-bromo-2-(3,4-dichlorophenyl)-1-methyl-4,5-bis(trifluoromethyl)pyrrole Chemical compound FC(F)(F)C1=C(C(F)(F)F)N(C)C(C=2C=C(Cl)C(Cl)=CC=2)=C1Br CXIBBZMZNFNDNH-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- IVDHYYCFEMRCDZ-UHFFFAOYSA-N 2-(trifluoromethyl)-1h-pyrrole Chemical compound FC(F)(F)C1=CC=CN1 IVDHYYCFEMRCDZ-UHFFFAOYSA-N 0.000 claims 1
- AEDUTYSZICKIPG-UHFFFAOYSA-N 3-bromo-2-(3,4-dichlorophenyl)-1-(ethoxymethyl)-4,5-bis(trifluoromethyl)pyrrole Chemical compound FC(F)(F)C1=C(C(F)(F)F)N(COCC)C(C=2C=C(Cl)C(Cl)=CC=2)=C1Br AEDUTYSZICKIPG-UHFFFAOYSA-N 0.000 claims 1
- IQCCHCHCXQSTHR-UHFFFAOYSA-N 3-bromo-2-(3,4-dichlorophenyl)-4,5-bis(trifluoromethyl)-1h-pyrrole Chemical compound FC(F)(F)C1=C(C(F)(F)F)NC(C=2C=C(Cl)C(Cl)=CC=2)=C1Br IQCCHCHCXQSTHR-UHFFFAOYSA-N 0.000 claims 1
- PTARIZTZVFEFBH-UHFFFAOYSA-N 5-(trifluoromethyl)-3,4-dihydro-2h-pyrrole Chemical compound FC(F)(F)C1=NCCC1 PTARIZTZVFEFBH-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 33
- 238000012360 testing method Methods 0.000 description 32
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- 239000007787 solid Substances 0.000 description 27
- 239000007788 liquid Substances 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 241000196324 Embryophyta Species 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 239000003921 oil Substances 0.000 description 15
- 238000009472 formulation Methods 0.000 description 14
- 239000012267 brine Substances 0.000 description 13
- 239000000284 extract Substances 0.000 description 13
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- 239000002917 insecticide Substances 0.000 description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 8
- 229910052783 alkali metal Inorganic materials 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 230000003595 spectral effect Effects 0.000 description 8
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 7
- 238000011156 evaluation Methods 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
- 239000000642 acaricide Substances 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 229940093499 ethyl acetate Drugs 0.000 description 6
- 235000019439 ethyl acetate Nutrition 0.000 description 6
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 244000045232 Canavalia ensiformis Species 0.000 description 5
- 241001521235 Spodoptera eridania Species 0.000 description 5
- 241000607479 Yersinia pestis Species 0.000 description 5
- 238000010586 diagram Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- KWVPFECTOKLOBL-KTKRTIGZSA-N 2-[(z)-octadec-9-enoxy]ethanol Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCO KWVPFECTOKLOBL-KTKRTIGZSA-N 0.000 description 4
- 241001124076 Aphididae Species 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- 241000256244 Heliothis virescens Species 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 235000008504 concentrate Nutrition 0.000 description 4
- 235000011167 hydrochloric acid Nutrition 0.000 description 4
- 229960000443 hydrochloric acid Drugs 0.000 description 4
- 150000002923 oximes Chemical class 0.000 description 4
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 239000000454 talc Substances 0.000 description 4
- 229910052623 talc Inorganic materials 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 206010001497 Agitation Diseases 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 241001414720 Cicadellidae Species 0.000 description 3
- 241000995027 Empoasca fabae Species 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 230000002152 alkylating effect Effects 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 230000009969 flowable effect Effects 0.000 description 3
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 238000000227 grinding Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- CMKCVJZWOPPOMM-UHFFFAOYSA-N 2-bromo-5-(4-chlorophenyl)-3,4-bis(trifluoromethyl)-1h-pyrrole Chemical compound FC(F)(F)C1=C(Br)NC(C=2C=CC(Cl)=CC=2)=C1C(F)(F)F CMKCVJZWOPPOMM-UHFFFAOYSA-N 0.000 description 2
- ONZQYZKCUHFORE-UHFFFAOYSA-N 3-bromo-1,1,1-trifluoropropan-2-one Chemical compound FC(F)(F)C(=O)CBr ONZQYZKCUHFORE-UHFFFAOYSA-N 0.000 description 2
- FPGXXLGDGFUGLN-UHFFFAOYSA-N 3-bromo-2-(3,4-dichlorophenyl)-4,5-bis(trifluoromethyl)pyrrole-1-carbonitrile Chemical compound N#CN1C(C(F)(F)F)=C(C(F)(F)F)C(Br)=C1C1=CC=C(Cl)C(Cl)=C1 FPGXXLGDGFUGLN-UHFFFAOYSA-N 0.000 description 2
- GCZALKJOOCILPK-UHFFFAOYSA-N 5-(4-chlorophenyl)-2,3-bis(trifluoromethyl)-1h-pyrrole Chemical compound N1C(C(F)(F)F)=C(C(F)(F)F)C=C1C1=CC=C(Cl)C=C1 GCZALKJOOCILPK-UHFFFAOYSA-N 0.000 description 2
- 241001524388 Abrupta Species 0.000 description 2
- 241001425390 Aphis fabae Species 0.000 description 2
- 241000238658 Blattella Species 0.000 description 2
- 241000238657 Blattella germanica Species 0.000 description 2
- 241001674044 Blattodea Species 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 description 2
- 235000010617 Phaseolus lunatus Nutrition 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- WFAULHLDTDDABL-UHFFFAOYSA-N Proxazole citrate Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.C=1C=CC=CC=1C(CC)C1=NOC(CCN(CC)CC)=N1 WFAULHLDTDDABL-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 229920001400 block copolymer Polymers 0.000 description 2
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- FCYRSDMGOLYDHL-UHFFFAOYSA-N chloromethoxyethane Chemical compound CCOCCl FCYRSDMGOLYDHL-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000013601 eggs Nutrition 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000007046 ethoxylation reaction Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 230000000361 pesticidal effect Effects 0.000 description 2
- AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical class ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 2
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 2
- 229940001584 sodium metabisulfite Drugs 0.000 description 2
- 235000010262 sodium metabisulphite Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000004546 suspension concentrate Substances 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- 241001478887 unidentified soil bacteria Species 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- JQZAEUFPPSRDOP-UHFFFAOYSA-N 1-chloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C=C1 JQZAEUFPPSRDOP-UHFFFAOYSA-N 0.000 description 1
- WLODWTPNUWYZKN-UHFFFAOYSA-N 1h-pyrrol-2-ol Chemical compound OC1=CC=CN1 WLODWTPNUWYZKN-UHFFFAOYSA-N 0.000 description 1
- SHCMZKABVGMMIZ-UHFFFAOYSA-N 2,3-bis(trifluoromethyl)-1h-pyrrole Chemical compound FC(F)(F)C=1C=CNC=1C(F)(F)F SHCMZKABVGMMIZ-UHFFFAOYSA-N 0.000 description 1
- HDICVSBKNVOGKQ-UHFFFAOYSA-N 2-(4-chlorophenyl)-3,4-bis(trifluoromethyl)-1h-pyrrole Chemical compound FC(F)(F)C1=CNC(C=2C=CC(Cl)=CC=2)=C1C(F)(F)F HDICVSBKNVOGKQ-UHFFFAOYSA-N 0.000 description 1
- UUGORHHVGPMOCD-UHFFFAOYSA-N 2-(4-chlorophenyl)-3,5-bis(trifluoromethyl)-1h-pyrrole Chemical compound N1C(C(F)(F)F)=CC(C(F)(F)F)=C1C1=CC=C(Cl)C=C1 UUGORHHVGPMOCD-UHFFFAOYSA-N 0.000 description 1
- QKBKGNDTLQFSEU-UHFFFAOYSA-N 2-bromo-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C(Br)=C QKBKGNDTLQFSEU-UHFFFAOYSA-N 0.000 description 1
- WBIQQQGBSDOWNP-UHFFFAOYSA-N 2-dodecylbenzenesulfonic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O WBIQQQGBSDOWNP-UHFFFAOYSA-N 0.000 description 1
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 1
- FKTNTKPCXIKFBJ-UHFFFAOYSA-N 3-(4-chlorophenyl)-1,1,1-trifluoropropan-2-one Chemical compound FC(F)(F)C(=O)CC1=CC=C(Cl)C=C1 FKTNTKPCXIKFBJ-UHFFFAOYSA-N 0.000 description 1
- FRMNBPMUOJJGPN-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-hydroxy-2,5-bis(trifluoromethyl)pyrrole Chemical compound ON1C(C(F)(F)F)=CC(C=2C=CC(Cl)=CC=2)=C1C(F)(F)F FRMNBPMUOJJGPN-UHFFFAOYSA-N 0.000 description 1
- UJLOBBJCWICZNX-UHFFFAOYSA-N 3-bromo-2-phenyl-4,5-bis(trifluoromethyl)-1h-pyrrole Chemical class FC(F)(F)C1=C(C(F)(F)F)NC(C=2C=CC=CC=2)=C1Br UJLOBBJCWICZNX-UHFFFAOYSA-N 0.000 description 1
- BGEVEELWQMIMDV-UHFFFAOYSA-N 4-bromo-2-(4-chlorophenyl)-3,5-bis(trifluoromethyl)-1h-pyrrole Chemical compound BrC1=C(C(F)(F)F)NC(C=2C=CC(Cl)=CC=2)=C1C(F)(F)F BGEVEELWQMIMDV-UHFFFAOYSA-N 0.000 description 1
- PKDIRAFBNLLJNZ-UHFFFAOYSA-N 5-(2-chlorophenyl)-2,3-bis(trifluoromethyl)-2,4-dihydropyrrol-3-ol Chemical compound FC(F)(F)C1C(O)(C(F)(F)F)CC(C=2C(=CC=CC=2)Cl)=N1 PKDIRAFBNLLJNZ-UHFFFAOYSA-N 0.000 description 1
- 101150052147 ALLC gene Proteins 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 241000239290 Araneae Species 0.000 description 1
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000489976 Diabrotica undecimpunctata howardi Species 0.000 description 1
- 229920005682 EO-PO block copolymer Polymers 0.000 description 1
- 241000995023 Empoasca Species 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical class F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 description 1
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical class NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- SZYOFORPKNXYIA-UHFFFAOYSA-N N1C=CC=C1.[Br] Chemical compound N1C=CC=C1.[Br] SZYOFORPKNXYIA-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000005708 Sodium hypochlorite Substances 0.000 description 1
- 244000062793 Sorghum vulgare Species 0.000 description 1
- STSCVKRWJPWALQ-UHFFFAOYSA-N TRIFLUOROACETIC ACID ETHYL ESTER Chemical compound CCOC(=O)C(F)(F)F STSCVKRWJPWALQ-UHFFFAOYSA-N 0.000 description 1
- 241000208241 Tropaeolum Species 0.000 description 1
- 240000001260 Tropaeolum majus Species 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 230000009418 agronomic effect Effects 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- VEMKTZHHVJILDY-UXHICEINSA-N bioresmethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OCC1=COC(CC=2C=CC=CC=2)=C1 VEMKTZHHVJILDY-UXHICEINSA-N 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 238000011284 combination treatment Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 239000010440 gypsum Substances 0.000 description 1
- 229910052602 gypsum Inorganic materials 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- GAQGGOBTZCONNR-UHFFFAOYSA-N methyl 4-chlorosulfanyl-n-(trimethylsilylmethyl)benzenecarboximidate Chemical compound C[Si](C)(C)CN=C(OC)C1=CC=C(SCl)C=C1 GAQGGOBTZCONNR-UHFFFAOYSA-N 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- KAXTWDXRCMICEQ-UHFFFAOYSA-N n-[1-(4-chlorophenyl)ethylidene]hydroxylamine Chemical compound ON=C(C)C1=CC=C(Cl)C=C1 KAXTWDXRCMICEQ-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- NBNBICNWNFQDDD-UHFFFAOYSA-N sulfuryl dibromide Chemical compound BrS(Br)(=O)=O NBNBICNWNFQDDD-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- 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
- C07D207/32—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
-
- 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
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/600,054 US5157047A (en) | 1990-10-18 | 1990-10-18 | Bis- and tris(trifluoromethyl)arylpyrrole insecticidal and acaricidal agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL99209A0 IL99209A0 (en) | 1992-07-15 |
| IL99209A true IL99209A (en) | 1996-05-14 |
Family
ID=24402174
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9920991A IL99209A (en) | 1990-10-18 | 1991-08-16 | Bis-and tris (trifluoromethyl) arylpyrroles process for their preparation and insecticidal and acaricidal compositions containing them |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US5157047A (de) |
| EP (1) | EP0481182B1 (de) |
| JP (1) | JPH04288054A (de) |
| AT (1) | ATE148455T1 (de) |
| AU (1) | AU646693B2 (de) |
| BR (1) | BR9104517A (de) |
| CA (1) | CA2053513C (de) |
| DE (1) | DE69124452T2 (de) |
| DK (1) | DK0481182T3 (de) |
| ES (1) | ES2096604T3 (de) |
| GR (1) | GR3022451T3 (de) |
| IL (1) | IL99209A (de) |
| PT (1) | PT99242B (de) |
| ZA (1) | ZA918295B (de) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5328928A (en) * | 1990-05-11 | 1994-07-12 | American Cyanamid Company | N-acylated arylpyrroles useful as insecticidal, agents |
| 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 |
| US5151536A (en) * | 1990-12-17 | 1992-09-29 | American Cyanamid Company | Process for the manufacture of pesticidal 1-(alkoxymethyl) pyrrole compounds |
| US5254559A (en) * | 1991-12-04 | 1993-10-19 | American Cyanamid Company | Insecticidal, acaricidal and molluscicidal 1-(substituted)thioalkylpyrroles |
| DE4233885A1 (de) * | 1992-10-08 | 1994-04-14 | Bayer Ag | Substituierte 2-Arylpyrrole |
| US5286743A (en) * | 1992-10-27 | 1994-02-15 | American Cyanamid Company | N-aminoalkylcarbonyloxyalkylpyrrole insecticidal acaricidal and molluscicidal agents |
| US5232980A (en) * | 1992-10-27 | 1993-08-03 | American Cyanamid Company | N-substituted carbonyloxyalkylpyrrole insecticidal, acaricidal and molluscicidal agents |
| US5286741A (en) * | 1992-10-27 | 1994-02-15 | American Cyanamid Company | N-oxy- and thioalkylcarbonyloxyalkylpyrrole insecticidal, acaricidal and molluscicidal agents |
| US5286742A (en) * | 1992-11-03 | 1994-02-15 | American Cyanamid Company | Pyrrole thiocarboxamide insecticidal and acaricidal agents |
| US5449789A (en) * | 1992-11-30 | 1995-09-12 | American Cyanamid Company | Debrominative chlorination of pyrroles |
| DE4325132A1 (de) * | 1993-07-27 | 1995-02-02 | Bayer Ag | Substituierte 2-Aryl-trifluormethylpyrrole |
| US5480902A (en) * | 1993-08-31 | 1996-01-02 | American Cyanamid Company | Thienylpyrrole fungicidal agents |
| US5492925A (en) * | 1993-08-31 | 1996-02-20 | American Cyanamid Company | Thienyl-and furylpyrrole insecticidal and acaricidal agents |
| US5932520A (en) * | 1995-05-23 | 1999-08-03 | American Cyanamid Company | Use of pyrrole compounds as antifouling agents |
| US5908858A (en) * | 1996-04-05 | 1999-06-01 | Sankyo Company, Limited | 1,2-diphenylpyrrole derivatives, their preparation and their therapeutic uses |
| IT1312355B1 (it) * | 1999-06-17 | 2002-04-15 | Isagro Ricerca Srl | Composti pirrolici aventi elevata attivita' erbicida e loro utilizzoagronomico |
| GB9930750D0 (en) | 1999-12-29 | 2000-02-16 | Novartis Ag | Organic compounds |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL6512721A (de) * | 1964-03-25 | 1966-04-13 | ||
| US4303667A (en) * | 1979-05-25 | 1981-12-01 | Nippon Soda Company Limited | Phenylprrole derivatives |
| EP0182737A3 (de) * | 1984-10-16 | 1986-10-08 | Ciba-Geigy Ag | 3-Phenylpyrrolderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel |
| IL87222A (en) * | 1987-07-29 | 1993-04-04 | American Cyanamid Co | Arylpyrroles, methods for thepreparation thereof andinsecticidal, acaricidal andnematicidal compositionscontaining them |
| EP0426948B1 (de) * | 1989-08-11 | 1996-05-08 | American Cyanamid Company | Arylpyrrol enthaltende insekticidale, acaricidale und nematicidale Mittel sowie Verfahren zu ihrer Herstellung |
| US5128485A (en) * | 1990-12-17 | 1992-07-07 | American Cyanamid Company | Synthesis of 2-aryl-5-(trifluoromethyl)pyrroles useful as pesticidal agents and as intermediates for the preparation of said agents |
-
1990
- 1990-10-18 US US07/600,054 patent/US5157047A/en not_active Expired - Lifetime
-
1991
- 1991-08-10 DK DK91113460.9T patent/DK0481182T3/da active
- 1991-08-10 AT AT91113460T patent/ATE148455T1/de not_active IP Right Cessation
- 1991-08-10 DE DE69124452T patent/DE69124452T2/de not_active Expired - Fee Related
- 1991-08-10 ES ES91113460T patent/ES2096604T3/es not_active Expired - Lifetime
- 1991-08-10 EP EP91113460A patent/EP0481182B1/de not_active Expired - Lifetime
- 1991-08-16 IL IL9920991A patent/IL99209A/en not_active IP Right Cessation
- 1991-10-16 JP JP3294759A patent/JPH04288054A/ja active Pending
- 1991-10-16 CA CA002053513A patent/CA2053513C/en not_active Expired - Fee Related
- 1991-10-16 PT PT99242A patent/PT99242B/pt not_active IP Right Cessation
- 1991-10-17 BR BR919104517A patent/BR9104517A/pt not_active Application Discontinuation
- 1991-10-17 ZA ZA918295A patent/ZA918295B/xx unknown
- 1991-10-17 AU AU85953/91A patent/AU646693B2/en not_active Ceased
-
1997
- 1997-01-31 GR GR960403688T patent/GR3022451T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATE148455T1 (de) | 1997-02-15 |
| JPH04288054A (ja) | 1992-10-13 |
| DE69124452T2 (de) | 1997-05-15 |
| CA2053513C (en) | 2003-02-25 |
| BR9104517A (pt) | 1992-06-09 |
| IL99209A0 (en) | 1992-07-15 |
| ZA918295B (en) | 1992-07-29 |
| DE69124452D1 (de) | 1997-03-13 |
| ES2096604T3 (es) | 1997-03-16 |
| PT99242A (pt) | 1992-09-30 |
| US5157047A (en) | 1992-10-20 |
| DK0481182T3 (da) | 1997-02-17 |
| PT99242B (pt) | 1999-04-30 |
| AU646693B2 (en) | 1994-03-03 |
| GR3022451T3 (en) | 1997-04-30 |
| EP0481182A1 (de) | 1992-04-22 |
| AU8595391A (en) | 1992-04-30 |
| CA2053513A1 (en) | 1992-04-19 |
| EP0481182B1 (de) | 1997-01-29 |
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