IL103089A - Process for the manufacture of insecticidal, nematicidal and acaricidal 2-aryl-3-substituted-5- (trifluoromethyl) pyrrole compounds from n-substituted benzyl)-2,2,2- trifluoroacetimidoyl chloride compounds - Google Patents
Process for the manufacture of insecticidal, nematicidal and acaricidal 2-aryl-3-substituted-5- (trifluoromethyl) pyrrole compounds from n-substituted benzyl)-2,2,2- trifluoroacetimidoyl chloride compoundsInfo
- Publication number
- IL103089A IL103089A IL103089A IL10308992A IL103089A IL 103089 A IL103089 A IL 103089A IL 103089 A IL103089 A IL 103089A IL 10308992 A IL10308992 A IL 10308992A IL 103089 A IL103089 A IL 103089A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- base
- solvent
- molar
- process according
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 19
- 230000000895 acaricidal effect Effects 0.000 title abstract description 4
- 230000000749 insecticidal effect Effects 0.000 title abstract description 4
- 238000004519 manufacturing process Methods 0.000 title abstract description 4
- 230000001069 nematicidal effect Effects 0.000 title abstract 2
- 150000002148 esters Chemical class 0.000 claims abstract description 10
- 150000002828 nitro derivatives Chemical class 0.000 claims abstract description 10
- 239000002585 base Substances 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 17
- -1 formamide acetonitrile tetrahydrofuran Chemical group 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 8
- 150000001805 chlorine compounds Chemical class 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 3
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- 229940126062 Compound A Drugs 0.000 claims 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims 1
- 241000212342 Sium Species 0.000 claims 1
- RRUROMNUPPONFR-UHFFFAOYSA-L [Na+].[Na+].[O-]C([O-])=O.CCN(CC)CC Chemical group [Na+].[Na+].[O-]C([O-])=O.CCN(CC)CC RRUROMNUPPONFR-UHFFFAOYSA-L 0.000 claims 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 1
- 125000005587 carbonate group Chemical group 0.000 claims 1
- 229940125904 compound 1 Drugs 0.000 claims 1
- 229940126214 compound 3 Drugs 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 abstract description 6
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 229940086542 triethylamine Drugs 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- OYUNTGBISCIYPW-UHFFFAOYSA-N 2-chloroprop-2-enenitrile Chemical compound ClC(=C)C#N OYUNTGBISCIYPW-UHFFFAOYSA-N 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- WUIRKDMXJRSDPX-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-2,2,2-trifluoroethanimidoyl chloride Chemical compound FC(F)(F)C(Cl)=NCC1=CC=C(Cl)C=C1 WUIRKDMXJRSDPX-UHFFFAOYSA-N 0.000 description 3
- ZXLQPJBQKJYNGN-UHFFFAOYSA-N 2-(4-chlorophenyl)-5-(trifluoromethyl)-1h-pyrrole-3-carbonitrile Chemical compound N1C(C(F)(F)F)=CC(C#N)=C1C1=CC=C(Cl)C=C1 ZXLQPJBQKJYNGN-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- FHRBKTYGPURYRT-UHFFFAOYSA-N n-[(2-chlorophenyl)methyl]-2,2,2-trifluoroethanimidoyl chloride Chemical compound FC(F)(F)C(Cl)=NCC1=CC=CC=C1Cl FHRBKTYGPURYRT-UHFFFAOYSA-N 0.000 description 2
- MGZRBHWCLPJTJQ-UHFFFAOYSA-N n-[(3,4-dichlorophenyl)methyl]-2,2,2-trifluoroethanimidoyl chloride Chemical compound FC(F)(F)C(Cl)=NCC1=CC=C(Cl)C(Cl)=C1 MGZRBHWCLPJTJQ-UHFFFAOYSA-N 0.000 description 2
- DEXVYKWXVWAYGO-UHFFFAOYSA-N n-benzyl-2,2,2-trifluoroacetamide Chemical class FC(F)(F)C(=O)NCC1=CC=CC=C1 DEXVYKWXVWAYGO-UHFFFAOYSA-N 0.000 description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
- PCYWMDGJYQAMCR-UHFFFAOYSA-N 1h-pyrrole-3-carbonitrile Chemical compound N#CC=1C=CNC=1 PCYWMDGJYQAMCR-UHFFFAOYSA-N 0.000 description 1
- RJJDLPQZNANQDQ-UHFFFAOYSA-N 2,3-dichloropropanenitrile Chemical compound ClCC(Cl)C#N RJJDLPQZNANQDQ-UHFFFAOYSA-N 0.000 description 1
- FSTDETBEBVWNJI-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-(trifluoromethyl)-1h-pyrrole-3-carbonitrile Chemical compound N1C(C(F)(F)F)=CC(C#N)=C1C1=CC=CC=C1Cl FSTDETBEBVWNJI-UHFFFAOYSA-N 0.000 description 1
- NEUIJIALUXKKKR-UHFFFAOYSA-N 2-(4-chloro-3-nitrophenyl)-5-(trifluoromethyl)-1h-pyrrole-3-carbonitrile Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC(C2=C(C=C(N2)C(F)(F)F)C#N)=C1 NEUIJIALUXKKKR-UHFFFAOYSA-N 0.000 description 1
- VELCWUVCHSZXRP-UHFFFAOYSA-N 2-(4-nitrophenyl)-5-(trifluoromethyl)-1h-pyrrole-3-carbonitrile Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=C(C#N)C=C(C(F)(F)F)N1 VELCWUVCHSZXRP-UHFFFAOYSA-N 0.000 description 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 description 1
- 108010081348 HRT1 protein Hairy Proteins 0.000 description 1
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 240000004120 Syzygium malaccense Species 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- JSERFYFLHUVKCE-UHFFFAOYSA-N n-[(4-chloro-3-nitrophenyl)methyl]-2,2,2-trifluoroacetamide Chemical compound [O-][N+](=O)C1=CC(CNC(=O)C(F)(F)F)=CC=C1Cl JSERFYFLHUVKCE-UHFFFAOYSA-N 0.000 description 1
- YFLMJLSWCJBGBW-UHFFFAOYSA-N n-[(4-chloro-3-nitrophenyl)methyl]-2,2,2-trifluoroethanimidoyl chloride Chemical compound [O-][N+](=O)C1=CC(CN=C(Cl)C(F)(F)F)=CC=C1Cl YFLMJLSWCJBGBW-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003233 pyrroles Chemical class 0.000 description 1
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
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
- 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cephalosporin Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/756,639 US5145986A (en) | 1991-09-09 | 1991-09-09 | Process for the manufacture of insecticidal, nematicidal and acaricidal 2-aryl-3-substituted-5-(trifluoromethyl)pyrrole compounds from N-(substituted benzyl)-2,2,2-trifluoro-acetimidoyl chloride compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL103089A0 IL103089A0 (en) | 1993-02-21 |
| IL103089A true IL103089A (en) | 1998-03-10 |
Family
ID=25044398
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL103089A IL103089A (en) | 1991-09-09 | 1992-09-07 | Process for the manufacture of insecticidal, nematicidal and acaricidal 2-aryl-3-substituted-5- (trifluoromethyl) pyrrole compounds from n-substituted benzyl)-2,2,2- trifluoroacetimidoyl chloride compounds |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US5145986A (de) |
| EP (1) | EP0531702B1 (de) |
| JP (1) | JP3138547B2 (de) |
| KR (1) | KR100236237B1 (de) |
| AT (1) | ATE201667T1 (de) |
| BR (1) | BR9203477A (de) |
| DE (1) | DE69231843T2 (de) |
| ES (1) | ES2157891T3 (de) |
| HU (1) | HU213026B (de) |
| IL (1) | IL103089A (de) |
| ZA (1) | ZA926833B (de) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5446170A (en) * | 1994-11-22 | 1995-08-29 | American Cyanamid Company | Process for the manufacture of insecticidal arylpyrroles via oxazole amine intermediates |
| US5631379A (en) * | 1994-11-22 | 1997-05-20 | American Cyanamid Company | Oxazole amines as intermediates in the manufacture of insecticidal pyrroles |
| US5945538A (en) * | 1996-06-28 | 1999-08-31 | American Cyanamid Company | Ammonium oxazole and amino oxazolium intermediates, methods for the preparation thereof and the use therefor in the manufacture of insecticidal arylpyrroles |
| US5777132A (en) * | 1996-06-28 | 1998-07-07 | American Cyanamid Company | Process for the manufacture of 2-aryl-5 perfluoroalkylpyrrole derivatives |
| US5750726A (en) * | 1996-06-28 | 1998-05-12 | American Cyanamid Company | Process for the manufacture of 2-aryl-5-perfluoroalkylpyrrole derivatives and intermediates useful therefor |
| US5925773A (en) * | 1996-06-28 | 1999-07-20 | American Cyanamid Company | Ammonium oxazole and amino oxazolium intermediates, methods for the preparation thereof and the use thereof in the manufacture of insecticidal arylpyrroles |
| IL128343A0 (en) * | 1998-02-09 | 2000-01-31 | American Cyanamid Co | Process for the preparation of 2-aryl-5-(perfluoroalkyl) pyrrole compounds from N-(arylmethylene)-1-chloro-1-(perfluoroalkyl) methylamine compounds |
| US6133455A (en) * | 1998-02-09 | 2000-10-17 | American Cyanamid Company | Process for the preparation of 2-aryl-5(perfluoro-alkyl) pyrrole compounds from N-(arylmethylene)-1-chloro-1-(perfluoroalkyl) methylamine compounds |
| US5965773A (en) * | 1998-02-09 | 1999-10-12 | American Cyanamid Company | Process for the preparation of 2-aryl-5-(perfluoroalkyl) pyrrole compounds from N-(perfluoroalkylmethyl) arylimidoyl chloride compounds |
| US6011161A (en) * | 1998-02-09 | 2000-01-04 | American Cyanamid Company | Process for the preparation of 2-aryl-5-(perfluoroalkyl)pyrrole compounds from N-(perfluoro-alkylmethyl)arylimidoyl chloride compounds |
| US5817834A (en) * | 1998-02-09 | 1998-10-06 | American Cyanamid Company | Process for the preparation of 2-aryl-5-(perfluoro-alkyl) pyrrole compounds from N-(perfluoroalkyl-methyl) arylimidoyl chloride compounds |
| IL134856A0 (en) * | 1999-03-09 | 2001-05-20 | American Cyanamid Co | Process for the preparation of 2-aryl-5-(perfluoroalkyl)pyrrole compounds from n-[1-chloro-1-(perfluoroalkyl) methyl]arylimidoyl choride compounds |
| US6320059B1 (en) | 2000-03-07 | 2001-11-20 | American Cyanamid Company | Process for the preparation of 2-aryl-5-(perfluoro-alkyl) pyrrole compounds from N-[1-chloro-1-(perfluoroalkyl) methyl] arylimidoyl chloride compounds |
| KR100998556B1 (ko) | 2010-04-08 | 2010-12-07 | 강원대학교산학협력단 | 신규한 다치환 피롤 유도체와 이의 제조방법 |
| CN118772034A (zh) * | 2024-09-12 | 2024-10-15 | 山东亿嘉农化有限公司 | 一种2-对氯苯基-5-（三氟甲基）吡咯-3-腈的制备工艺 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5010098A (en) * | 1987-07-29 | 1991-04-23 | American Cyanamid Company | Arylpyrrole insecticidal acaricidal and nematicidal agents and methods for the preparation thereof |
| EP0358047A3 (de) * | 1988-09-08 | 1991-05-29 | American Cyanamid Company | Verfahren zur Bekämpfung von phytopathogenen Pilzen |
| US5068390A (en) * | 1990-07-31 | 1991-11-26 | American Cyanamid Company | 1,1,1-trifluoro-2-propene compounds |
| US5030735A (en) * | 1990-07-31 | 1991-07-09 | American Cyanamid Company | Process for the preparation of insecticidal, acaricidal and nematicidal 2-aryl-5-(trifluoromethyl) pyrrole compounds |
| 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 |
| ES2131044T3 (es) * | 1990-12-26 | 1999-07-16 | American Cyanamid Co | Procedimiento para la preparacion de compuestos 2-aril-5-(trifluorometil)pirrol 1-sustituidos utiles como agentes insecticidas, acaricidas y nematocidas y como intermedios para la fabricacion de dichos agentes. |
-
1991
- 1991-09-09 US US07/756,639 patent/US5145986A/en not_active Expired - Lifetime
-
1992
- 1992-08-03 AT AT92113210T patent/ATE201667T1/de active
- 1992-08-03 ES ES92113210T patent/ES2157891T3/es not_active Expired - Lifetime
- 1992-08-03 DE DE69231843T patent/DE69231843T2/de not_active Expired - Lifetime
- 1992-08-03 EP EP92113210A patent/EP0531702B1/de not_active Expired - Lifetime
- 1992-09-04 JP JP04260496A patent/JP3138547B2/ja not_active Expired - Lifetime
- 1992-09-07 IL IL103089A patent/IL103089A/en not_active IP Right Cessation
- 1992-09-08 KR KR1019920016399A patent/KR100236237B1/ko not_active Expired - Fee Related
- 1992-09-08 BR BR929203477A patent/BR9203477A/pt not_active IP Right Cessation
- 1992-09-08 HU HU9202872A patent/HU213026B/hu not_active IP Right Cessation
- 1992-09-08 ZA ZA926833A patent/ZA926833B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL103089A0 (en) | 1993-02-21 |
| BR9203477A (pt) | 1993-04-13 |
| EP0531702A1 (de) | 1993-03-17 |
| DE69231843T2 (de) | 2001-10-25 |
| ES2157891T3 (es) | 2001-09-01 |
| JPH05194383A (ja) | 1993-08-03 |
| KR930005975A (ko) | 1993-04-20 |
| JP3138547B2 (ja) | 2001-02-26 |
| ATE201667T1 (de) | 2001-06-15 |
| DE69231843D1 (de) | 2001-07-05 |
| US5145986A (en) | 1992-09-08 |
| KR100236237B1 (ko) | 2001-11-22 |
| EP0531702B1 (de) | 2001-05-30 |
| HUT62857A (en) | 1993-06-28 |
| HU213026B (en) | 1997-01-28 |
| HU9202872D0 (en) | 1992-11-30 |
| ZA926833B (en) | 1993-03-15 |
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