KR920012022A - 아릴피롤 화합물 및 이의 제조방법 - Google Patents

아릴피롤 화합물 및 이의 제조방법 Download PDF

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KR920012022A
KR920012022A KR1019910024311A KR910024311A KR920012022A KR 920012022 A KR920012022 A KR 920012022A KR 1019910024311 A KR1019910024311 A KR 1019910024311A KR 910024311 A KR910024311 A KR 910024311A KR 920012022 A KR920012022 A KR 920012022A
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alkyl
hydrogen
halogen
alkoxy
chlorophenyl
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케임즈와란 벤카타라만
프랜시스 도우너 쥬니어 로버트
마이클 바아턴 제리
조오지 쿠운 데이빗
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알퐁스 아아르 노에
아메리칸 사이아나밋드 캄파니
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    • C07D207/18—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 one double bond between ring members or between a ring member and a non-ring member
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    • 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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Abstract

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Description

아릴피롤 화합물 및 이의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (13)

  1. 하기 일반 구조식을 특징으로 하는 화합물 :
    (상기식에서, A는 수소 또는 C1-C4알킬이고, W는 CN, NO2또는 CO2R6이고, L은 수소 또는 할로겐이며, M 및 R은 각각 독립적으로 수소, C1-C4알킬, C1-C4알콕시, C1-C4알킬티오, C1-C4알킬설피닐, C1-C4알킬설포닐, CN, NO2, 할로겐, CF3, F1, CF2, Z, R2CO 또는 NR3R4이며, M 및 R이 이웃한 위치에 있을 때, 이들은 이들이 결합된 탄소원자와 함께 취해져서 MR이 하기 구조식 : -OCH2O-, -OCF2O- 또는 -CH=CH-CH=CH-을 나타내는 고리를 형성하고, Z는 S(O)n 또는 O이고, R1은 수소, F, CHF2, CHFCl 또는 CF3이고, R2는 C1-C4알킬, C1-C4알콕시 또는 NR3R4이고, R3는 수소 또는 C1-C4알킬이고, R4는 수소, C1-C4알킬 또는 R5CO이고, R5는 수소 또는 C1-C4알킬이며, R6는 C1-C6알킬, C3-C6시클로알킬 또는 페닐이고, n은 0.1 또는 2의 정수이다)|
  2. 제1항에 있어서, 2-(p-클로로페닐)-1-메틸-5-(트리플루오로메틸)-2-피롤린-3-카르보니트릴 및 2-(p-클로로페닐)-5-(트리플루오로메틸)-2-피롤린-3-카르보니트릴로 구성된 군으로 선택되는 화합물.
  3. 하기 일반구조식을 특징으로 하는 화합물 :
    상기 식에서, A는 수소 또는 C1-C4알킬이고, L은 수소 또는 할로겐이며, M 및 R은 각각 독립적으로 수소, C1-C3알킬, C1-C3알콕시, C1-C3알킬티오, C1-C3알킬설피닐, C1-C3알킬설포닐, CN, NO2, 할로겐, CF3, R1CF2Z, R2CO 또는 NR3R4이며, M 및 R이 이웃한 위치에 있을 때, 이들은 이들이 결합된 탄소원자와 함께 취해져서 MR이 하기구조식 :-OCH2O-, -OCF2O- 또는 -CH=CH-CH=CH-을 나타내는 고리를 형성하고, 단, A가 수소일 때, L, M 및 R중 적어도 하나는 수소 이외의 다른 것이어야만 하며, Z는 S(O)n 또는 0이고, R1은 수소, F, CHF2, CHFCl 또는 CF3이고, R2는 C1-C4알킬, C1-C4알콕시 또는 NR3R4이고, R3는 수소 또는 C1-C4알킬이고, R4는 수소, C1-C4알킬 또는 R5CO이고, R5는 수소 또는 C1-C4알킬이며, R6는 C1-C6알킬, C3-C6시클로 알킬 또는 페닐이고, n은 0, 1 또는 2의 정수이다)
  4. 제3항에 있어서, 2-(p-클로로페닐)-N-(트리플루오로아세틸)사르코신 및 2-(p-클로로페닐)-N-(트리플루오로아세틸)글리신으로 구성된 군으로부터 선택되는 화합물.
  5. 산 무수물 및 용매의 존재하에 하기 일반식 구조식(Ⅱ),
    (상기 식에서, A는 수소 또는 C1-C4알킬이고, L은 수소 또는 할로겐이며, M 및 R은 각각 독립적으로 수소, C1-C3알킬, C1-C3알콕시, C1-C3알킬티오, C1-C3알킬설피닐, C1-C3알킬설포닐, CN, NO2, 할로겐, CF3, R1CF2Z, R2CO 또는 NR3R4이며, M 및 R이 이웃한 위치에 있을 때, 이들은 이들이 결합된 탄소원자와 함게 취해져서 MR이 하기구조식 :-OCH2O-, -OCF2O- 또는 -CH=CH-CH=CH-을 나타내는 고리를 형성하고, Z는 S(O)n 또는 0이고, R1은 수소, F, CHF2, CHFCl 또는 CF3이고, R2는 C1-C4알킬, C1-C4알콕시 또는 NR3R4이고, R3는 수소 또는 C1-C4알킬이고, R4는 수소, C1-C4알킬 또는 R5CO이고, R5는 수소 또는 C1-C4알킬이며, C6는 C1-C6알킬, C3-C6시클로 알킬 또는 페닐이고, n은 0.1 또는 2의 정수이다)을 하기 일반구조식 :H2C=CHW(상기식에서, W는 CN, NO2또는 CO2R6이다)을 갖는 약1몰 당량의 올레핀 및 임의적으로 촉매량의 유기염기와 반응시키는 것으로 구성된, 하기 일반 구조식(Ⅰ) :
    (상기 식에서, A, L, M 및 R은 상기 정의된 바와 같다)을 특징으로 하는 화합물의 제조방법.
  6. 용매의 존재하에 하기 일반 구조식 :
    (상기 식에서, L은 수소 또는 할로겐이며, M 및 R은 각각 독립적으로 수소, C1-C3알킬, C1-C3알콕시, C1-C3알킬티오, C1-C3알킬설피닐, C1-C3알킬설포닐, CN, NO2, 할로겐, CF3, R1CF2Z, R2CO 또는 NR3R4이며, M 및 R이 이웃한 위치에 있을 때, 이들은 이들이 결합된 탄소원자와 함께 취해져서 MR이 하기구조식 :-OCH2O-, -OCF2O- 또는 -CH=CH-CH=CH-을 나타내는 고리를 형성하고, 단, A가 수소일 때, L, M 및 R중 적어도 하나는 수소 이외의 다른 것이어야만 하며, Z는 S(O)n 또는 0이고, R1은 수소, F, CHF2, CHFCl 또는 CF3이고, R2는 C1-C4알킬, C1-C4알콕시 또는 NR3R4이고, R3는 수소 또는 C1-C4알킬이고, R4는 수소, C1-C4알킬 또는 R5CO이고, R5는 수소 또는 C1-C4알킬이며, R6는 C1-C6알킬, C3-C6시클로 알킬 또는 페닐이고, n은 0, 1 또는 2의 정수이다)을 하기 일반 구조식 : N2N-A·HCl(상기식에서, A는 수소 또는 C1-C4알킬이다)을 갖는 적어도 1몰 당량의 아민 염산염과 반응시켜 중간체를 형성시키고, 상기 중간체 용액을 적어도 1몰 당량의 알칼리 금속 시안화물을 함유한 수용액과 반응시켜 아미노 니트릴 중간체를 형성시키고, 임의적으로 고온에서 물의 존재하에 상기 아미도 니트릴을 광산과 반응시켜 아미노 산 중간체를 산출시키고, 상기 중간체를 삼불화 아세트산 무수물과 반응시켜 하기 일반 구조식(Ⅱ)를 갖는 바람직한 화합물을 산출하는 것을 특징으로 하는, 하기 일반 구조식(Ⅱ) :
    (상기식에서, A, L, M 및 R은 상기 정의된 바와 같다)을 특징으로 하는 화합물의 제조방법.
  7. 용매의 존재하에, 하기 일반 구조식(V)
    (상기식에서, W는 CN, NO2또는 CO2R2이고, L은 수소 또는 할로겐이며, M 및 R은 각각 독립적으로 수소, C1-C4알킬, C1-C4알콕시, C1-C4알킬티오, C1-C4알킬설피닐, C1-C4알킬설피닐, CN, NO2, Cl, Br, F, I, CF3, R3CF2Z, R4CO 또는 NR5R6이며, M 및 R이 이웃한 위치에 있을 때 이들은 이들이 결합된 탄소원자와 함께 취해져서 MR이 하기 구조식 : -OCH2O-, -OCF2O- 또는 -CH=CH-CH=CH-을 나타내는 고리를 형성하고, R2는 C1-C6알킬, C3-C6시클로알킬 또는 페닐, R3는 수소, F, CHF2, CHFCl또는 CF3, R4는 C1-C4알킬, C1-C4알킬 또는 NR5R6, R5는 수소 또는 C1-C4알킬, R6는 수소, C1-C4알킬 또는 R7CO, R7는 수소 또는 C1-C4알킬, Z는 S(O)n 또는 O 및 n는 0, 1 또는 2의 정수이다)을 적어도 1당량의 할로겐, X2(이때, X2는 Br, Cl 또는 I이다)과 반응시켜, 2-아릴-1-메틸피롤 중간체를 얻고, 상기 1-메틸피를 중간체를 상기 할로겐의 적어도 1첨가 몰 당량과 반응시켜 2-아릴-4-할로-1-메틸피를 중간체를 형성시키고, 라디칼 개시제의 존재하에, 상기 4-할로-1-메틸피를 중간체를 부가적으로 상기 할로겐의 적어도 1몰 당량과 반응시켜 2-아릴-4-할로-1-(할로메틸)피를 중간체를 형성하고, 상기 4-할로-1-(할로메틸)피를 중간체를 적어도 1몰 당량의 알칼리 금속 C1-C6알콕시드와 반응시켜, 이란 구조식 Ⅰ의 화합물을 산출하는 것으로 구성되는, 하기 일반 구조식(Ⅳ) :
    (상기식에서, R1은 C1-C6알킬이고, X는 Br, Cl 또는 I이고, W, L, M 및 R은 상기 정의된 바와 같다)을 특징으로 하는 화합물의 제조방법.
  8. 제9항에 있어서, 하기 일반 구조식을 특징으로 하는 방법에 따라 제조된 생성물.
    상기식에서, R1은 C1-C6알킬이고, W는 CN, NO2또는 CO2R6이고, L은 수소 또는 할로겐이며, M 및 R은 각각 독립적으로 수소, C1-C4알킬, C1-C4알콕시, C1-C4알킬티오, C1-C4알킬설포닐, C1-C4알킬설포닐, CN, NO2, Cl, Br, F, I, CF2, R3, CF2, Z, R4CO 또는 NR5R6이며, M 및 R이 이웃한 위치에 있을 때 이들은 이들이 결합된 탄소원자와 함께 취해져서, MR이 하기 구조식 : -OCH2O-, -OCF2O- 또는 -CH=CH-CH=CH-을 나타내는 고리를 형성하고, R2는 C1-C6알킬, C3-C6시클로알킬 또는 페닐이고, R3는 수소, F, CHF2, CHFCl 또는 CF3이고, R4는 C1-C4알킬이고, C1-C4알킬 또는 NR5R6, R5는 수소 또는 C1-C4알이고킬, R6는 수소, C1-C4알킬 또는 R7CO이고, R7는 수소 또는 C1-C4알이고킬, Z는 S(O)n 또는 O 및 n는 0, 1 또는 2의 정수이다.
  9. 4-클로로-1-(클로로메틸)-2-(p-클로로페닐)-5-(트리플루오로메틸)-피롤-3-카르보니트릴, 4-브로모-1-(브로모메틸)-2-(p-클로로페닐)-5-(트리플루오로메틸)-피롤-3-카르보니트릴 및 4-클로로-1-(에톡시메틸)-2-(p-클로로페닐)-5-(트리플루오로메틸)피롤-3-카르보니트릴로 구성된 군으로부터 선택된 화합물.
  10. 살충성, 선충박멸성 또는 진드기 구충성 유효량의 4-클로로-1-(에톡시메틸)-2-(p-클로로페닐)-5-(트리플루오로메틸)피롤-3-카르보니트릴을, 식물의 잎 또는 식물이 성장하고 있는 토양 또는 물에 적용시키는 것을 특징으로 하는 곤충, 선충 및 진드기에 의한 공격으로부터 식물을 보호하는 방법.
  11. 살충성, 선충박멸성 또는 진드기 구충성 유효량의 4-클로로-1-(에톡시메틸)-2-(p-클로로페닐)-5-(트리플루오로메틸)피롤-3-카르보니트릴을 곤충, 선충 및 진드기, 사육장, 먹이 공급원 또는 서식지와 접촉시키는 것을 특징으로 하는 곤충, 선충 및 진드기를 구제하는 방법.
  12. 살충성, 선충 박멸성 또는 진드기 구충성 유효량의 피롤카르보니트릴 화합물을 함유한 농경법상 허용가능한 담체를 특징으로 하는 곤충, 선충 및 진드기에 의한 공격으로부터 성장하는 식물을 보호하기 위한 조성물.
  13. 살충성, 선충박멸성 또는 진드기 구충성 유효량의 피롤카르보니트릴 화합물을 함유한 농경법상 허용가능한 담체를 특징으로 하는, 곤충, 선충 및 진드기를 구제하는 조성물.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019910024311A 1990-12-26 1991-12-24 아릴피롤 화합물 및 이의 제조 방법 KR100217319B1 (ko)

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US07/634,288 US5194630A (en) 1990-12-26 1990-12-26 Process for the manufacture of insecticidal 2-aryl-1-(alkoxymethyl)-4-halo-5-(trifluoromethyl)pyrroles
US07/634,287 US5118816A (en) 1990-12-26 1990-12-26 2-aryl-5-(trifluoromethyl)-2-pyrroline compounds useful in the manufacture of insecticidal, nematocidal and acaricidal arylpyrroles
US07/634,288 1990-12-26
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EP0492093B1 (en) * 1990-12-26 1999-03-17 American Cyanamid Company Process for the preparation of 2-aryl 1-substituted-5-(trifluoromethyl)pyrrole compounds useful as insecticidal, acaricidal and nematocidal agents and as intermediates for the manufacture of said agents
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
DE4217725A1 (de) * 1992-05-29 1993-12-02 Bayer Ag Substituierte 2-Arylpyrrole
DE4217722A1 (de) * 1992-05-29 1993-12-02 Bayer Ag Substituierte 2-Arylpyrrole
FR2713640B1 (fr) * 1993-12-15 1996-01-05 Cird Galderma Nouveaux composés aromatiques polycycliques, compositions pharmaceutiques et cosmétiques les contenant et utilisations.
AU722204B2 (en) * 1995-10-31 2000-07-27 Sumitomo Chemical Company, Limited Pesticidal composition
JP4126621B2 (ja) * 1996-11-25 2008-07-30 日本農薬株式会社 殺虫・殺ダニ剤
GB0813042D0 (en) * 2008-07-16 2008-08-20 Syngenta Participations Ag Insecticidal compounds
CN102731363B (zh) * 2011-12-15 2013-09-25 青岛农业大学 一组吡咯杀虫剂化合物
AU2016259360B1 (en) * 2016-11-16 2017-09-07 Rotam Agrochem International Company Limited A novel crystalline form of chlorfenapyr, a process for its preparation and use of the same
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US4891442A (en) * 1987-03-09 1990-01-02 Texaco Inc. Process for synthesis of β-phenylalanine
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