KR890000429A - N-페닐 피라졸류의 제조방법 - Google Patents

N-페닐 피라졸류의 제조방법 Download PDF

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KR890000429A
KR890000429A KR1019880007045A KR880007045A KR890000429A KR 890000429 A KR890000429 A KR 890000429A KR 1019880007045 A KR1019880007045 A KR 1019880007045A KR 880007045 A KR880007045 A KR 880007045A KR 890000429 A KR890000429 A KR 890000429A
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죠오지 벤테인 이안
로이 하톤 레슬리
윌리암 호킨스 데이비드
존 피어선 크리스토퍼
알란 로버츠 데이비드
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테리 페터 밀러
메이 앤드 베이커 리미티드
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Abstract

내용 없음

Description

N-페닐 피라졸류의 제조방법.
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (14)

  1. 하기 일반식(I)의 N-페닐피라졸 유도체.
    [상기식중, R1은 시아노 또는 니트로기, 할로겐원자 또는 아세틸 또는 포르밀기를 나타내고; R2는 기 R5SO2, R5SO 또는 R5S(식중, R5는 같거나 서로 다를 수 있는 하나 이상의 할로겐원자에 의해 치환 또는 비치환될 수 있는 4이하의 탄소원자를 함유한 직쇄- 또는 측쇄-알킬, 알케닐 또는 알카닐기를 나타낸다)를 나타내며; R3는 수소원자 또는 아미노기 -NR6R7(식중, R6및 R7은 같거나 서로 다르며 각각 수소원자 또는 5이하의 탄소원자를 함유한 직쇄- 또는 측쇄 알킬, 알케닐알킬 또는 알키닐알킬기, 포르밀기, 하나 이상의 할로겐 원자에 의해 임의 치환될 수 있는 2~5 탄소원자를 함유한 직쇄 또는 측쇄 알카노일기를 나타내거나, R6및 R7은 그에 부착된 질소원자와 함께 5 또는 6원 고리형 이미드를 형성하거나, 하나 이상의 할로겐 원자에 의해 치환 또는 비치환된 2~5탄소원자를 함유한 직쇄-또는 측쇄 알콕시카르보닐기를 나타낸다.)를 나타내거나, R3는 1~4 탄소원자를 함유한 직쇄 또는 측쇄알킬기에 의해 메틸렌이 치환 또는 비치환될 수 있는 2~5 탄소원자를 함유한 직쇄 또는 측쇄 알콕시메틸렌 아미노기를 나타내거나, 할로겐원자를 나타내고; R4는 플루오르, 염소, 브롬 또는 요오드 원자에 의해 2-위치가, 같거나 서로 다를 수 있는 하나 이상의 할로겐 원자에 의해 치환 또는 비치환 될 수 있는 1~4 탄소원자를 함유한 직쇄 또는 알킬 도는 알콕시기, 또는 염소 또는 브롬원자에 이해 4-위치가, 및 임의로 플루오로, 염소, 브롬 또는 요오드원자에 의해 6-위치가 치환된 페닐기를 나타내며; 단 R1이 시아노를 나타내고, R2가 메탄술포닐을 나타내며, R3가 아미노를 나타내고, R4가 2,6-디클로로-4-트리플루오로메틸페닐을 나타내는 화합물은 제외한다].
  2. 제1항에 있어서, R1이 포르밀기 이외의 기이고, R6또는 R7이 알케닐알킬 또는 알키닐알킬기를 나타내지 않는 화합물.
  3. 제1항에 있어서, R2가 임의로 할로겐 치환된 1~4 탄소원자를 함유한 알킬술포닐/술피닐/티오기, 또는 임의로 할로겐 치환된 4이하의 탄소원자를 함유한 알케닐-또는 알키닐-술포닐/-술피닐/티오기를 나타내고, R3가 수소원자, 아미노 또는 메틸아미노기를 나타내며, R1이 할로겐원자 또는 시아노 또는 니트로기를 나타내는 화합물.
  4. 제3항에 있어서, R1이 시아노 또는 니트로기를 나타내는 화합물.
  5. 제1~4항중 어느 한항에 있어서, R4가 트리플루오로메틸 또는 트리플루오로메톡시기를 함유하며, R2가 1~4탄소원자를 함유한 임의로 할로겐화된 알킬술포닐/술피닐/티오기를 나타내는 화합물.
  6. 제5항에 있어서, R2가 트리플루오로메틸티오, 트리플루오로메틸술피닐 또는 트리플루오로메닐 술포닐기를 나타내는 화합물.
  7. 제1~6항중 어느 한 항에 있어서, R4가 2,4,6-트리클로로-2,6-디클로로-4-디플루오로메톡시-2-클로로-4-트리플루오로메틸-2-브로모-6-클로로-4-트리플루오로메틸-2,6-디브로모-4-트리플루오로메틸-또는 2-브로모-4-틀리플루오로메틸-페닐기를 나타내는 화합물.
  8. 제1~6항중 어느 한 항에 있어서, R4가 2,6-디클로로-4-트리플루오로메틸-또는 2,6-디클로로-4-트리플루오로메톡시-페닐기를 나타내는 화합물.
  9. 제1항에 있어서, 화합물번호 1~101중 어느 하나로 표시된 화합물.
  10. (a) R2가 R5SO2, R5SO 또는 R5S기를 나타내고, R3가 비치환아미노기를 나타내며, R1이 시아노 또는 아세틸기를 나타낼때, 일반식
    (식중, R8은 시아노 또는 아세틸기를 나타내고, R4는 제1항에 정의한 바와 같다)의 화합물을 일바닉 R2CH2CN(식중, R2는 제1항에 정의한 바와 같다)의 화합물과 반응시키거나; (b) R2가 R5S기를 나타내고, R3가 아미노기 -NR6R7(식중, R6및 R7은 각각 수소원자 또는 제1항에 정의한 바와 같은 직쇄 또는 측쇄 알킬, 알케닐알킬 또는 알키닐알킬기를 나타낸다)를 나타낼때, R2가 수소원자로 치환된 일반식(I)에 상응하는 화합물을 일반식
    R5-SCI (III)
    (식중, R5는 제1항에 정의한 바와 같다)의 화합물과 반응시키거나; (C) R1이 염소 또는 플루오로원자를 나타내고, R2가 R5SO2, R5SO 또는 R5S기를 나타내며, R3가 아미노기를 나타낼때, 일반식
    (식중, X 및 Y는 둘다 염소원자를 나타내거나, 둘다 플루오르원자를 나타낸다)의 화합물을 일반식
    R4NHNH2(V)
    (식중, R4는 제1항에 정의한 바와 같다)의 페닐 히드라진 또는 그의 산부가염과 반응시키거나; (d) (1)R2가 R5S기를 나타내고, R1이 염소, 브롬, 요오드 또는 플로오르원자 또는 시아노 또는 니트로기를 나타내며, R3가 아미노기를 나타낼때 R2가 티오시아나토기로 치환된 일반식(I)에 상응하는 화합물을 일반식
    R5-Mg-X1(VI)
    (식중, R5는 제1항에 정의한 바와 같고, X1은 할로겐원자이다)의 화합물 또는 일반식
    R9-C=C-Li+(IX)
    (식중, R9-C=C-는 일반식(I)의 R5에 상응한다)의 화합물과 반응시키거나; (d) (2) R2가 R5S기(식중, R5S는 1-알케닐티오 또는 1-알키닐티오기 이외의 기이다)를 나타낼때, R2가 티오시아 나토기로 치환된 일반식(I)에 상응하는 화합물을 일반식
    R5′-X2(VII)
    (식중, R5′는 1-알케닐 및 1-알키닐을 제외하고는 제1항의 R5에서 정의한 바와같고, X2는 할로겐원자를 나타낸다)의 시약 존재하에 염기 또는 환원제와 반응시키거나, 일반식
    F2C=C(Z)(Z′) (VIIA)
    (식중, Z는 플루오르, 염소 또는 브롬원자를 나타내고, Z′는 Z에서 정의한 것 또는 트리플루오르 메틸기를 나타낸다)의 화합물 존재하에 염기와 반응시키거나; (d) (3) R5S가 1-알케닐티오 또는 1-알키닐티오기 이외의 기일때, 일반식
    (식중, R1, R3및 R4는 제1항에 정의한 바와 같다)의 디설파이드를 염기 및 일반식(VII) (식중, R5′는 상기에서 정의한 바와 같다)의 할라이드 존재하에 환원제를 사용하여 환원적 알킬화하거나; (e) R2가 R5SO 또는 R5SO2기를 나타낼때, R2가 R5S를 나타내는 일반식 I의 화합물에서 황원자를 산화시키거나; (f) R1이 플루오르, 염소, 브롬 또는 요오드원자 또는 시아노 또는 니트로기를 나타낼 때, R1이 아미노기로 치환되고, R3가 수소원자 또는 아미노기를 나타내는 일반식(I)에 상응하는 화합물을 디아조화하고, 디아조화된 아미노기 R1을 공지방법에 의해 플루오르, 염소, 브롬 또는 요오드원자 또는 시아노 또는 니트로기로 전환시키거나, R3가 할로겐원자를 나타낼때, R3가 아미노길ㄹ 나타내는 일반식(I)의 화합물을 디아조화하고, 디아조화된 아미노기 R3를 공지방법에 의해 할로겐원자로 전화시키거나; (g) R1이 플루오르원자 또는 시아노기를 나타내고, R3가 수소원자 또는 아미노기를 나타낼때, R1이 염소 또는 브롬원자를 나타내는 일반식(I)의 할라이드를 알칼리금속 플루오라이드 또는 금속 시아나이드와 반응시켜 염소 또는 브롬원자를 플루오르원자 또는 시아노기로 전환시키거나; (h) R1이 니트로기를 나타내고, R2가 R5SO2또는 R5SO를 나타낼때, R1이 비치환 아미노기로 치환되고, R2가 기 R5SO2, R5SO 또는 R5S이며, R3가 수소원자 또는 아미노기를 나타내는 일반식(I)에 상응하는 화합물을 산화제와 반응시켜 비치환아미노기를 니트로기 R1으로 전환시키거나;
    (i) R1이 시아노기를 나타내고, R3가 수소원자 또는 아미노기를 나타낼때, R1이 카르바모일기로 치환된 일반식(I)에 상응하는 화합물을 탈수시키거나; (j) R1이 아세틸기이고, R3가 수소원자 또는 아미노기를 나타낼때, R1이 시아노기인 일반식(I)의 상응하는 니트릴 또는 R1이 알콕시카르보닐기 CO2R(식중, R은 1~6 탄소원자를 함유한 직쇄 또는 측쇄 알킬기를 나타낸다)로 치환된 상응하는 에스테르, 또는 R1이 카르복시기로 치환된 카르복실산을 메틸리튬과 반응시키거나, R1이 시아노기인 일반식(I)의 니트릴 또는 R1이 알콕시카르보닐기 CO2R로 치환된 에스테르를 그리나드시약 CH3MgX3(식중, X3는 할로겐원자를 나타낸다)과 반응시키거나; (k) R1이 아세틸기를 나타내고, R3가 상기에 정의한 바와 같을때, R1이 히드록시에틸기로 치환된 일반식(I)에 상응하는 알콜을 산화제로 산화시키거나; (l) R1이 포르밀기를 나타내고, R3가 상기에 정의한 바와 같을 때, R1이 시아노기를 나타내는 일반식(I)의 상응하는 니트릴을 환원제와 반응시키고 산 가수분해하거나, 포름산 중에서 라니니켈과 반응시켜 시아노기를 포르밀기로 전환시키거나; (m) R3가 아미노기 -NR6R7을 나타내는 일반식(I)의 화합물을 공지방법에 의해 R3가 다른 아미노기 -NR6R7을 나타내는 일반식(I)의 화합물로 전환시키거나;
    (n) R3가 1~4탄소원자를 함유한 직쇄- 또는 측쇄 알킬기에 의해 메틸렌이 치환 또는 비치환될 수 있는 2~5 탄소원자를 함유한 직쇄- 또는 특쇄 알톡시메틸렌 아미노기를 나타낼때, R3가 비치환 아미노기를 나타내는 일반식(I)의 화합물을 트리스알콕시알칸과 반응시키거나; (o) R3가 기 -NHCH2R16(식중, R16은 수소원자 또는 1~4탄소원자를 함유한 직쇄 또는 측쇄 알킬기를 나타낸다)를 나타낼때, R3가 기 -N=C(OR17)R16(식중, R17은 1~4 탄소원자를 함유한 직쇄 또는 측쇄 알킬기를 나타낸다)를 나타내는 일반식(I)의 화합물을 환원제와 반응시키거나; (p) R1이 포르밀, 아세틸, 시아노 또는 니트로기를 나타내고, R3가 플루오르원자를 나타낼때, R3가 염소 또는 브롬원자를 나타내는 일반식(I)의 화합물과 할로겐 교환 반응시키거나; (q) R3가 수소원자를 나타낼 때, R3가 아미노기를 나타내는 일반식(I)의 화합물을 용매중 및 주변온도~환류온도에서 디아조화제와 반응시켜 아미노기 R3를 수소원자로 전환시키거나; (r) R1이 시아노 또는 니트로기를 나타내고, R2가 기 R5SO2를 나타내며, R6및 R7이 각각 5이하의 탄소원자를 함유한 직쇄 또는 측쇄 알킬, 알케닐알킬 또는 알키닐알킬기를 나타내고, R7이 수소원자를 나타낼 수도 있을때, R3가 할로겐원자를 나타내는 일반식(I)의 화합물을 일반식 R6R7NH내의 상응하는 아민과 반응시키거나, R6및 R7이 모두 메틸일때 디메틸히드라진과 반응시키거나; 임의로 상기에서 수득된 일반식(I)의 화합물을 일반식(I)의 또다른 화합물로 전환시킴을 특징으로 하는 제1항에 따른 화합물의 제조방법.
  11. 일반식(I)의 화합물을 하나이상의 병용 가능한 희석제 또는 담체와 함께 함유하는 살 절지동물, 살 식물선충, 구충 또는 항 원충 조성물.
  12. 유효량의 제1항에 따른 화합물로 필요부분을 처리함을 특징으로 하는 필요부분에서 절지동물, 식물선충, 기생충 또는 원충류의 억제방법.
  13. 절지동물, 기생충 또는 원충류 감염 처리를 위한 약품제조용 제1항에 정의된 일반식(I)의 화합물.
  14. 하기 일반식(XXV)의 화합물.
    [상기 식중, R2′는 정의한 바와 같거나, 수소원자, 티오시아나토, 포르밀, 시아노 또는 카르복실기, 2~7 탄소원자를 함유한 직쇄-또는 측쇄 알콕시카르보닐기 또는 디티오기(두 피라졸 고리가 연합됨)를 나타내고; R3′는 제1항의 R3에 정의한 바와 같거나, 디페녹시카르보닐아미노기를 나타내며; R1′는 제1항의 R1에 정의한 바와 같거나, 아미노, 1-히드록시에틸, 카르복시 또는 카르바모일기 또는 2~7 탄소원자를 함유한 직쇄 또는 측쇄 알킬카르보닐 또는 알콕시카르보닐아미노기를 나타내고; 단지 제1항에 정의된 일반식(I)의 화합물 및 일반식(XXV)의 화합물중에서, R4가 2,6-디클로로-4-트리플루오로메틸페닐을 나타내고, R2′가 시아노기를 나타내며, R1′가 시아노기를 나타내고, R3′가 아미노, 아세트아미도, 디클로로아세트아미도, t-부틸 카르보닐아미노, 프로피온아미도, 펜탄아미도, 비스(에톡시카르보닐)아미노, 에톡시카르보닐아미노, 메틸아미노 또는 에틸아미노기를 나타내거나, R1′가 염소원자를 나타내고, R3′가 아미노, t-부틸카르보닐아미노, 비스(에톡시카르보닐) 아미노 또는 에톡시카르보닐아미노기를 나타내거나,
    R1′가 브롬 또는 요오드원자 또는 아미노 또는 에톡시카르보닐기를 나타내고, R3′가 아미노기를 나타내거나, R1′가 플루오르원자를 나타내고, R3′가 수소원자 또는 아미노기를 나타내거나, R1′ 가 니트로, 아미노, t-부톡시카르보닐아미노 또는 에톡시카르보닐기를 나타내고, R3′가 수소 원자를 나타내는 화합물 R4가 2,4,6-트리클로로페닐, 2-클로로-4-트리플루오로메틸페닐 또는 2,6-디클로로-4-트리플루오로메톡시페닐기를 나타내고, R2′가 시아노기를 나타내며, R1′가 시아노기를 나타내고, R3′가 아미노기를 나타내는 화합물; R4가 2,6-디클로로-4-트리플루오로메톡시페닐기를 나타내고, R2′가 시아노기를 나타내며, R1′가 염소원자를 나타내고, R3′가 시아미노를 나타내는 화합물; 및 R4가 2,6-디클로로-4-트리플루오로메틸페닐기를 나타내고, R2′가 메탄술포닐기를 나타내며, R1′가 카르복시, 카르바모일 또는 에톡시카르보닐기를 나타내고, R3′가 아미노기를 나타내는 화합물은 제외한다].
    ※참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019880007045A 1987-06-12 1988-06-11 N-페닐 피라졸 유도체 KR970001475B1 (ko)

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