KR930005975A - 2-아릴-3-치환-5-(트리플루오로메틸)피롤 화합물의 제조방법 - Google Patents

2-아릴-3-치환-5-(트리플루오로메틸)피롤 화합물의 제조방법 Download PDF

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KR930005975A
KR930005975A KR1019920016399A KR920016399A KR930005975A KR 930005975 A KR930005975 A KR 930005975A KR 1019920016399 A KR1019920016399 A KR 1019920016399A KR 920016399 A KR920016399 A KR 920016399A KR 930005975 A KR930005975 A KR 930005975A
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compound
base
substituted
trifluoromethyl
aryl
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KR1019920016399A
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KR100236237B1 (ko
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카아메스와란 벤카타라만
조오지 쿠운 데이빗
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알퐁스 아아르 노에
아메리칸 사이아나밋드 캄파니
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    • 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

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  • 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)
  • Pyrrole Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Cephalosporin Compounds (AREA)

Abstract

본 발명은, N-(치환벤질)-2,2,2-트리플루오로아세트이미도일 클로라이드 화합물과 α-할로, -α,β-불포화 니트릴, 에스테르 또는 니트로 화합물의 축합에 의한 살충성, 선충박멸성 및 진드기 구충성 2-아릴-3-치환-5-(트리플루오로메틸)피롤 화합물의 제조방법을 제공한다.

Description

2-아릴-3-치환-5-(트리플루오로메틸)피롤 화합물의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (10)

  1. 용매의 존재하에, 하기 일반식을 갖는 N-(치환벤질)-2,2,2-트리플루오로아세트이미도일 클로라이드 화합물:
    (이때, L, M 및 Q는 하기 서술된 바와 같음)을 하기 일반식을 갖는 α-할로-α,β-불포화 니트릴, 에스테르 또는 니트로 화합물 적어도 약 1몰 당량:
    (이때, W 및 Y는 하기 서술된 바와 같고, X는 Cl, Br 또는 I임) 및 염기 적어도 1몰 당량과 반응시켜 2-아릴-3-치환-5-(트리플루오로메틸)피롤 화합물을 형성하는 것으로 구성되는, 하기 일반식을 갖는 2-아릴-3-치환-5-(트리플루오로메틸)피롤 화합물의 제조방법.
    상기식에서 W는 H 또는 CF3이고, Y는 CN, NO2또는 CO2R이고, R은 C1-C4알킬이고, L은 C1-C4알킬이고, L은 H, F, Cl 또는 Br이고, M 및 Q는 각각 독립적으로 H, F, Cl, Br, I, CN, NO2, CF3, C1-C3알킬, C1-C3알콕시, C1-C3알킬설포닐, C1-C3알킬설피닐, C1-C3알킬티오 또는 R1CF2Z이고 Z는 S(0)n 또는 0이고, n은 1 또는 2의 정수이고, 및 R1은 H, F, CHF2, CHFCl 또는 CF3이다.
  2. 제1항에 있어서, α-할로-α,β-불포화 니트릴, 에스테르 또는 니트로 화합물은 약 1 내지 4몰 당량의 양으로 제공되고 염기는 약 1 내지 4몰 당량의 양으로 제공되는 방법.
  3. 제1항에 있어서, 염기는 알칼리 금속 카보네이트 또는 C1-C4트리알킬아민이고 용매는 N,N-디메틸포름아미드, 아세토니트릴, 테트라히드로푸란 또는 염화 메틸렌인 방법.
  4. 제3항에 있어서, 염기는 트리에틸아민, 탄산 나트륨 또는 탄산 칼륨이고 용매는 N,N-디메틸포름아미드 또는 아세토니트릴인 방법.
  5. 제1항에 있어서, W는 H이고, X는 Cl 또는 Br이고, Y는 CN이고, L은 H이고, M 및 Q는 각각 독립적으로 H, F, Cl, Br, CN NO2또는 CF3인 방법.
  6. 용매의 존재하에, 하기 일반식을 갖는 N-(치환벤질)-2,2,2-트리플루오로아세트이미도일 클로라이드 화합물:
    (이때, L, M 및 Q는 상기 서술된 바와 같음)을 하기 일반식을 갖는 α,β-티할로 니트릴, 에스테르 또는 니트로 화합물 저겅도 약 1몰 당량:
    (이때, W 및 Y는 하기 서술된 바와 같고, X는 Cl, Br 또는 I임) 및 염기 적어도 약 2몰 당량과 반응시켜 2-아릴-3-치환-5-(트리플루오로메틸)피롤 화합물을 형성하는 것으로 구성되는 하기 일반식을 갖는 2-아릴-3-치환-5-(트리플루오로메틸)피롤 화합물의 제조방법.
    상기식에서 W는 H 또는 CF3이고, Y는 CN, NO2또는 CO2R이고, R은 C1-C4알킬이고, L은 C1-C4알킬이고, L은 H, F, Cl 또는 Br이고, M 및 Q는 각각 독립적으로 H, F, Cl, Br, I, CN, NO2, CF3, C1-C3알킬, C1-C3알콕시, C1-C3알킬설포닐, C1-C3알킬설피닐, C1-C3알킬티오 또는 R1CF2Z이고 Z는 S(0)n 또는 0이고, n은 1 또는 2의 정수이고, 및 R1은 H, F, CHF2, CHFCl 또는 CF3이다.
  7. 제6항에 있어서, α,β-디할로 니트릴, 에스테르 또는 니트로 화합물은 약 1 내지 4몰 당량의 양으로 제공되고 염기는 약 2 내지 5몰 당량의 양으로 제공되는 방법.
  8. 제6항에 있어서, 염기는 알칼리 금속 카보네이트 또는 C1-C4트리알킬아민이고 용매는 N,N-디메틸포름아미드, 아세토니트릴, 테트라히드로푸란 또는 염화 메틸렌인 방법.
  9. 제8항에 있어서, 염기는 트리에틸아민, 탄산 나트륨 또는 탄산 칼륨이고 용매는 N,N-디메틸포름아미드 또는 아세토니트릴인 방법.
  10. 제6항에 있어서, W는 H이고, X는 Cl 또는 Br이고 Y는 CN이고 L은 H이고, M 및 Q는 각각 독립적으로 H, F, Cl, Br, CN, NO2또는 CF3인 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019920016399A 1991-09-09 1992-09-08 2-아릴-3-치환-5-(트리플루오로메틸)피롤화합물의제조방법 KR100236237B1 (ko)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US07/756,639 1991-09-09
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

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KR930005975A true KR930005975A (ko) 1993-04-20
KR100236237B1 KR100236237B1 (ko) 2001-11-22

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US (1) US5145986A (ko)
EP (1) EP0531702B1 (ko)
JP (1) JP3138547B2 (ko)
KR (1) KR100236237B1 (ko)
AT (1) ATE201667T1 (ko)
BR (1) BR9203477A (ko)
DE (1) DE69231843T2 (ko)
ES (1) ES2157891T3 (ko)
HU (1) HU213026B (ko)
IL (1) IL103089A (ko)
ZA (1) ZA926833B (ko)

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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
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
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
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
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
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
JP4485638B2 (ja) * 1999-03-09 2010-06-23 ワイス・ホールディングズ・コーポレイション 塩化ｎ−［１−クロロ−１−（ペルフルオロアルキル）メチル］アリールイミドイル化合物からの２−アリール−５−（ペルフルオロアルキル）ピロール化合物の製造方法
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

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US5010098A (en) * 1987-07-29 1991-04-23 American Cyanamid Company Arylpyrrole insecticidal acaricidal and nematicidal agents and methods for the preparation thereof
EP0358047A3 (en) * 1988-09-08 1991-05-29 American Cyanamid Company Method of controlling phytopathogenic fungi
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
US5068390A (en) * 1990-07-31 1991-11-26 American Cyanamid Company 1,1,1-trifluoro-2-propene 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
DK0492093T3 (da) * 1990-12-26 1999-09-27 American Cyanamid Co Fremgangsmåde til fremstilling af 2-aryl-1-substituerede-5-(trifluormethyl)-pyrrolforbindelser anvendelige som insekticide,

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BR9203477A (pt) 1993-04-13
IL103089A (en) 1998-03-10
DE69231843T2 (de) 2001-10-25
JPH05194383A (ja) 1993-08-03
ZA926833B (en) 1993-03-15
JP3138547B2 (ja) 2001-02-26
EP0531702B1 (en) 2001-05-30
DE69231843D1 (de) 2001-07-05
IL103089A0 (en) 1993-02-21
KR100236237B1 (ko) 2001-11-22
ATE201667T1 (de) 2001-06-15
HUT62857A (en) 1993-06-28
ES2157891T3 (es) 2001-09-01
HU9202872D0 (en) 1992-11-30
US5145986A (en) 1992-09-08
HU213026B (en) 1997-01-28
EP0531702A1 (en) 1993-03-17

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