CN1133836A - 通过噁唑胺中间体制备芳基吡咯杀昆虫剂的方法 - Google Patents
通过噁唑胺中间体制备芳基吡咯杀昆虫剂的方法 Download PDFInfo
- Publication number
- CN1133836A CN1133836A CN95118932A CN95118932A CN1133836A CN 1133836 A CN1133836 A CN 1133836A CN 95118932 A CN95118932 A CN 95118932A CN 95118932 A CN95118932 A CN 95118932A CN 1133836 A CN1133836 A CN 1133836A
- Authority
- CN
- China
- Prior art keywords
- alkyl
- halogen
- hydrogen
- haloalkyl
- compound
- 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
- 238000000034 method Methods 0.000 title claims abstract description 29
- -1 oxazole amine Chemical class 0.000 title claims description 27
- 230000000749 insecticidal effect Effects 0.000 title abstract description 4
- 238000004519 manufacturing process Methods 0.000 title abstract description 4
- 239000000543 intermediate Substances 0.000 title description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 27
- 150000002367 halogens Chemical class 0.000 claims description 27
- 238000002360 preparation method Methods 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 13
- 150000001721 carbon Chemical group 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 8
- 239000003513 alkali Substances 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 7
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 6
- 238000007363 ring formation reaction Methods 0.000 claims description 6
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 5
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910015900 BF3 Inorganic materials 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- RILZRCJGXSFXNE-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]ethanol Chemical compound OCCC1=CC=C(OC(F)(F)F)C=C1 RILZRCJGXSFXNE-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims 2
- 150000001266 acyl halides Chemical class 0.000 claims 1
- PCYWMDGJYQAMCR-UHFFFAOYSA-N 1h-pyrrole-3-carbonitrile Chemical compound N#CC=1C=CNC=1 PCYWMDGJYQAMCR-UHFFFAOYSA-N 0.000 abstract 1
- 230000000895 acaricidal effect Effects 0.000 abstract 1
- 238000006352 cycloaddition reaction Methods 0.000 abstract 1
- 239000005645 nematicide Substances 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
- 239000007787 solid Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- OYUNTGBISCIYPW-UHFFFAOYSA-N 2-chloroprop-2-enenitrile Chemical compound ClC(=C)C#N OYUNTGBISCIYPW-UHFFFAOYSA-N 0.000 description 5
- 238000000605 extraction Methods 0.000 description 5
- 239000002917 insecticide Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 238000003810 ethyl acetate extraction Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- 241001585712 Noctua Species 0.000 description 2
- 239000000642 acaricide Substances 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 2
- 150000003851 azoles Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000002574 poison Substances 0.000 description 2
- 231100000614 poison Toxicity 0.000 description 2
- 150000003233 pyrroles Chemical class 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- QHZVYZZRMVDSRK-UHFFFAOYSA-N 1,3-oxazole-2-sulfonamide Chemical class NS(=O)(=O)C1=NC=CO1 QHZVYZZRMVDSRK-UHFFFAOYSA-N 0.000 description 1
- QJQGMOIUEXCUOH-UHFFFAOYSA-N 1,3-oxazole;1h-pyrrole Chemical class C=1C=CNC=1.C1=COC=N1 QJQGMOIUEXCUOH-UHFFFAOYSA-N 0.000 description 1
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
- OFJBYLCQNJHFMI-UHFFFAOYSA-N 2,5-dihydro-1,2-oxazole Chemical compound C1ONC=C1 OFJBYLCQNJHFMI-UHFFFAOYSA-N 0.000 description 1
- GUGQQGROXHPINL-UHFFFAOYSA-N 2-oxobutanoyl chloride Chemical compound CCC(=O)C(Cl)=O GUGQQGROXHPINL-UHFFFAOYSA-N 0.000 description 1
- DKFAYHWIVQDPCC-UHFFFAOYSA-N 3-chloroprop-2-enenitrile Chemical compound ClC=CC#N DKFAYHWIVQDPCC-UHFFFAOYSA-N 0.000 description 1
- JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
- OKTJSMMVPCPJKN-OUBTZVSYSA-N Carbon-13 Chemical compound [13C] OKTJSMMVPCPJKN-OUBTZVSYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical class FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000256257 Heliothis Species 0.000 description 1
- 241000256248 Spodoptera Species 0.000 description 1
- 241001454295 Tetranychidae Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- KWHDXJHBFYQOTK-UHFFFAOYSA-N heptane;toluene Chemical compound CCCCCCC.CC1=CC=CC=C1 KWHDXJHBFYQOTK-UHFFFAOYSA-N 0.000 description 1
- 239000002955 immunomodulating agent Substances 0.000 description 1
- 229940121354 immunomodulator Drugs 0.000 description 1
- 230000002584 immunomodulator Effects 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- KRPAJLYSLFNDOA-UHFFFAOYSA-N mephenesin carbamate Chemical compound CC1=CC=CC=C1OCC(O)COC(N)=O KRPAJLYSLFNDOA-UHFFFAOYSA-N 0.000 description 1
- 229950006838 mephenesin carbamate Drugs 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N methyl alcohol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- QGNBDSPDXGLEJP-UHFFFAOYSA-N n-fluoroacetamide Chemical compound CC(=O)NF QGNBDSPDXGLEJP-UHFFFAOYSA-N 0.000 description 1
- FVSUYFWWFUVGRG-UHFFFAOYSA-N naphthalen-1-ylurea Chemical compound C1=CC=C2C(NC(=O)N)=CC=CC2=C1 FVSUYFWWFUVGRG-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002728 pyrethroid Substances 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003419 tautomerization reaction Methods 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
- C07D207/34—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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyrrole Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/343,147 | 1994-11-22 | ||
| US08/343,147 US5446170A (en) | 1994-11-22 | 1994-11-22 | Process for the manufacture of insecticidal arylpyrroles via oxazole amine intermediates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1133836A true CN1133836A (zh) | 1996-10-23 |
Family
ID=23344892
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN95118932A Pending CN1133836A (zh) | 1994-11-22 | 1995-11-22 | 通过噁唑胺中间体制备芳基吡咯杀昆虫剂的方法 |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US5446170A (enExample) |
| EP (1) | EP0713868B1 (enExample) |
| JP (1) | JP3781464B2 (enExample) |
| KR (1) | KR960017638A (enExample) |
| CN (1) | CN1133836A (enExample) |
| AR (1) | AR000173A1 (enExample) |
| AT (1) | ATE212012T1 (enExample) |
| AU (1) | AU701087B2 (enExample) |
| BR (1) | BR9505251A (enExample) |
| CA (1) | CA2163327A1 (enExample) |
| CZ (1) | CZ286772B6 (enExample) |
| DE (1) | DE69525021T2 (enExample) |
| ES (1) | ES2170785T3 (enExample) |
| HU (1) | HU217922B (enExample) |
| IL (1) | IL116070A0 (enExample) |
| SK (1) | SK143895A3 (enExample) |
| TW (1) | TW296379B (enExample) |
| ZA (1) | ZA959949B (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5659046A (en) * | 1993-12-30 | 1997-08-19 | American Cyanamid Company | Method for the preparation of 2-perfluoroalkyl-3-oxazolin-5-one |
| 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 |
| 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 |
| 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 |
| US5777132A (en) * | 1996-06-28 | 1998-07-07 | American Cyanamid Company | Process for the manufacture of 2-aryl-5 perfluoroalkylpyrrole derivatives |
| TW381087B (en) * | 1996-06-28 | 2000-02-01 | American Cyanamid Co | Ammonium oxazole and amino oxazolium intermediates, methods for the preparation thereof and the use therefor in the manufacture of insecticidal arylpyrroles |
| 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 |
| 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 |
| 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 |
| 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 |
| CN103058946A (zh) * | 2012-12-19 | 2013-04-24 | 浙江工业大学 | 一种2,5-二取代噁唑衍生物的制备方法 |
| JP7260480B2 (ja) | 2017-03-13 | 2023-04-18 | ビーエーエスエフ アグロ ベー．ブイ． | Ｄｉｐｅａ塩基の存在下でのアリールピロール化合物の製造 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US5118816A (en) * | 1990-12-26 | 1992-06-02 | American Cyanamid Company | 2-aryl-5-(trifluoromethyl)-2-pyrroline compounds useful in the manufacture of insecticidal, nematocidal and acaricidal arylpyrroles |
| YU8592A (sh) * | 1991-08-28 | 1994-06-10 | Flumroc Ag. | Postupak i uređaj za izradu ploča od mineralnih vlakana primenjenih kao nosač zidnog premaza |
| US5130328A (en) * | 1991-09-06 | 1992-07-14 | American Cyanamid Company | N-alkanoylaminomethyl and N-aroylaminomethyl pyrrole insecticidal and acaricidal agents |
| US5145986A (en) * | 1991-09-09 | 1992-09-08 | American Cyanamid Company | 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 |
| CN1074439A (zh) * | 1992-01-17 | 1993-07-21 | 中国科学院上海有机化学研究所 | 一种从三氟甲基唑酮合成三氟甲基吡咯类化合物的方法 |
| US5286743A (en) * | 1992-10-27 | 1994-02-15 | American Cyanamid Company | N-aminoalkylcarbonyloxyalkylpyrrole insecticidal acaricidal and molluscicidal agents |
| US5426225A (en) | 1993-12-30 | 1995-06-20 | American Cyanamid Company | Perfluoroalkanoyl aminonitriles |
-
1994
- 1994-11-22 US US08/343,147 patent/US5446170A/en not_active Expired - Lifetime
-
1995
- 1995-05-16 US US08/442,045 patent/US5574175A/en not_active Expired - Fee Related
- 1995-08-10 TW TW084108310A patent/TW296379B/zh active
- 1995-11-06 CZ CZ19952887A patent/CZ286772B6/cs not_active IP Right Cessation
- 1995-11-16 SK SK1438-95A patent/SK143895A3/sk unknown
- 1995-11-17 JP JP32383695A patent/JP3781464B2/ja not_active Expired - Fee Related
- 1995-11-20 CA CA002163327A patent/CA2163327A1/en not_active Abandoned
- 1995-11-21 AR AR33431495A patent/AR000173A1/es unknown
- 1995-11-21 DE DE69525021T patent/DE69525021T2/de not_active Expired - Lifetime
- 1995-11-21 EP EP95308298A patent/EP0713868B1/en not_active Expired - Lifetime
- 1995-11-21 BR BR9505251A patent/BR9505251A/pt not_active IP Right Cessation
- 1995-11-21 HU HU9503324A patent/HU217922B/hu not_active IP Right Cessation
- 1995-11-21 KR KR1019950042446A patent/KR960017638A/ko not_active Abandoned
- 1995-11-21 IL IL11607095A patent/IL116070A0/xx unknown
- 1995-11-21 AT AT95308298T patent/ATE212012T1/de not_active IP Right Cessation
- 1995-11-21 ES ES95308298T patent/ES2170785T3/es not_active Expired - Lifetime
- 1995-11-22 ZA ZA959949A patent/ZA959949B/xx unknown
- 1995-11-22 AU AU39017/95A patent/AU701087B2/en not_active Ceased
- 1995-11-22 CN CN95118932A patent/CN1133836A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IL116070A0 (en) | 1996-01-31 |
| KR960017638A (ko) | 1996-06-17 |
| CA2163327A1 (en) | 1996-05-23 |
| JPH08225522A (ja) | 1996-09-03 |
| HU9503324D0 (en) | 1996-01-29 |
| AU701087B2 (en) | 1999-01-21 |
| AU3901795A (en) | 1996-05-30 |
| US5446170A (en) | 1995-08-29 |
| DE69525021T2 (de) | 2002-07-18 |
| US5574175A (en) | 1996-11-12 |
| EP0713868B1 (en) | 2002-01-16 |
| CZ288795A3 (en) | 1996-06-12 |
| DE69525021D1 (de) | 2002-02-21 |
| ZA959949B (en) | 1997-05-22 |
| ES2170785T3 (es) | 2002-08-16 |
| HU217922B (hu) | 2000-05-28 |
| EP0713868A1 (en) | 1996-05-29 |
| JP3781464B2 (ja) | 2006-05-31 |
| HUT73018A (en) | 1996-06-28 |
| TW296379B (enExample) | 1997-01-21 |
| BR9505251A (pt) | 1997-09-16 |
| SK143895A3 (en) | 1996-09-04 |
| AR000173A1 (es) | 1997-05-21 |
| ATE212012T1 (de) | 2002-02-15 |
| CZ286772B6 (en) | 2000-07-12 |
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