KR900007311A - 살충제 - Google Patents

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KR900007311A
KR900007311A KR1019890016642A KR890016642A KR900007311A KR 900007311 A KR900007311 A KR 900007311A KR 1019890016642 A KR1019890016642 A KR 1019890016642A KR 890016642 A KR890016642 A KR 890016642A KR 900007311 A KR900007311 A KR 900007311A
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cyclopropyl
dieneamide
penta
methyl
trans
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KR0140890B1 (ko
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존 블라드 로버트
스튜어트 카커릴 조지
에드워드 로빈슨 존
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엠.피.잭슨
더 웰컴 화운데이션 리미티드
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Abstract

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Description

살충제
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (15)

  1. a) 위티그(Wittia)형 반응을 통해 하기식(Ⅰ)의 잔기를 형성하거나, b) X가 산소일때, 상응하는 산 또는 하기식(B)의 산유도체를 하기식(c)의 아민과 반응시킨 뒤, 임의로 기술분야에서 잘 알려진 방법으로 식(Ⅰ)의 화할물을 식(Ⅰ)의 화합물을 식(Ⅰ)의 다른 화합물로 전환시키는 것을 포함하는 하기식(Ⅰ)의 화합물 또는 그 염의 제조방법
    QQ1CR2=CR3CR4=CR5C(=X)NHR1(Ⅰ)
    tf; 식중, Q는 모노사이클 방향족 고리 또는 하나의 원자가 질소이고 나머지 탄소 각각의 고리 시스템이 임의로 치환된 9 또는 10개의 원자를 함유하는 방향족인 적어도 하나의 고리를 지닌 융해된 비사이클 고리시스템, 또는 Q는 디할로비닐기 또는 R6가 C1-4알킬, 트리 C1-4알킬실릴, 할로겐 또는 수소이며, Q1은 C1-3알킬, 할로 C1-3할로알킬, 알키닐, 또는 시아노로 부터 선택된 하나 이상의 기에 의해 임의 치환된 1, 2-시클로프로필 고리이며, R2, R3, R4및 R5는 동일하거나 서로 다르며, 적어도 하나는 수소이고, 나머지는 수소, 할로, C1-4알킬 또는 C1-4할로알킬로 부터 각각 선택되며 X는 산소 또는 황이며, R1은 수소 및 디옥살란일, 할로, 시아노, 트리플루오로 메틸, 트리플루오로메틸티오 또는 C1-6알콕시에 의해 임의 치환된 C1-5히드로 카르빌로 부터 선택된다.
    CR2=CR3CR4=CR5C(=X)NHR1(A)
    QQ1CR2=CR3CR4=CR5C(=X)Z' (B)
    H2NR1(C)
    상기 식중, Q,Q',R2, R3,R4,R5및 R1상기에서 정의한 바와 같으며 Z1은 히트록시, C1-6알콕시, 할로 또는 포스포로 이미데이트 에스테트(-P(0) (0-아릴)NH-아릴(여기서, 아릴은 C6-10=0아릴임이며, X는 산소이다.
  2. 제1항에 있어서, Q가, 내지 3개의 할로 또는 할로, 시아노 또는 너트로에 의해 각각 임의 치환된 C1-6히드로카르빌 C1-6알콕시 또는 메틸렌디옥시로 부터 선택된, 1내지 4개의 기에 의해 각각 임의 치환된 페닐, 피리닐, 티에닐 또는 나프틸기, 또는 치환체가 n=0, 1 또는 2이고, R7이 하나 또는 두개의 C1-6알킬 또는 R7이 하나 이상의 할토에 임의 치환된 C1-6알킬기에 의해 임의 치환된 아미노인 S(O)7NR7기 또는 회전체가 및 R8및 R9가 각각 수소, C1-6알킬로 부터 선택된 NR8R9기 또는 R10이 C1-6알킬인 COR10기인 것을 특징으로 하는(Ⅰ)의 화합물의 제조방법.
  3. 제1항 또는 제2항에 있어서, R2, R3,R4및 R5가 수소, 메틸 또는 플루오로로 부터 선택되는 것을 특징으로 하는 식(Ⅰ)의 화합물의 제조방법.
  4. 제1항 내지 제3항중 어느 한항에 있어서, 시클로프로필 고리 Q1은 비치환되고2-위치는 플루오로 또는 클로로에 의해 치환 또는 비치환 되는 것을 특징으로 하는 식(I)의 화합물의 제조방법.
  5. 제1항 내지 제4항중 어느 한항에 있어서, R1이소부틸, 1, 2-디메틸프로필, 1,1,2-트리메틸프로필, 2,2-디메틸프로필, 2-메틸프로프-2-에닐 또는 (2-메틸-1, 3-디옥산-2-일)메틸인 것을 특징으로 하는 식(I)의 화합물의 제조방법
  6. 하기식(Ⅱ) 또는 그 염의 제조방법.
    QaQ1aCR2a=CR3aCR4aCR5aC(=Xa)NHR1a(Ⅱ)
    상기식에서 Qa는 임의로 치환된 페닐 또는 페닐기, 또는 하나의 원자가 질소이고, 나머지가 탄소인 9 또는 10개의 원자를 함유하는 방향족인 적어도 하나의 고리를 지닌 융해된 비사이클 고리 시스템, 또는 Qa는 디할로비닐기 또는 R6a가 C1-4알킬, 트리알킬실릴 또는 수소인 R6a-C=C-기이며, Q19는 C1-3알킬, 할로 또는 X1-3할로알킬로 부터 선택된 하나이상의 기로 임의 치환된 1,2-시클로필로필 고리이며, R2a, R3a, R4a및 R5a는 동일하거나 사로 다르며, 적어도 하나는 수소이고, 나머지는 수소, 할로 C1-4알킬 또는 C1-4할로알킬로 부터 각각 선택되며, R1a는 소수 및 디옥살란일, 할로, 시아노, 트리플루오로 메틸, 트리플루오로메틸티오 는C1-6알콕시에 의해 임의 치완된 C1-6히드로카르빌로 부터 선택된다.
  7. (±)-(2E,43) N-이소부틸-3-메틸-5-메틸-5-[트랜스-2-(4-클로로 페닐)시클로프로필] 펜타-2,4-디엔아미드, (±)-(2E,4E) N-(2-메틸프로프-2-에닐)-3-메틸-5-[트랜스-2-(3,4-디브로모페닐)시클로프로필] 펜타-2,4-디엔아미드, (±)-(2E,4E) N-이소부틸-3-메틸-5-[트랜스-2-(3-트리플루오로메틸-4-클로로페닐)시클로프로필] 펜타-2-4디엔아미드, (±)-(2E,4E) N-이소부틸-3-메틸-5-[트랜스-2-(3.5-디클로로-4-브로모페닐) 시클로프로필] 펜타-2,4-디엔아미드, ±)-(2E,4E) N-이소부틸-3-메틸-5-[트랜스-8-(3,4,5-트리클로로-페닐) 시클로프로필] 펜타-2,4-디엔아미드, (±)-(2E,4E) N-이소부틸-3-메틸-4-플루오로-5-[트랜스-2-(3,4-디클로페닐) 시클로프로필] 펜타2,4-디엔아미드, (±)-(2E,4E) N-(1,2-디메틸프로필)5-[트랜스-2-(3-클로로-4-브로모페닐)시클로프로필] 펜타-2,4-디엔아미드, (±)-(2E,4E) N-이소부틸-3-메틸-5-[트랜스-2-(3-클로로-4-브로모페닐)시클로프로필] 펜타-2,4-디엔아미드, (±)-(2E,4E) N-(1,2-디메틸프로필)-5-[트랜스-2-(4-브로모페닐)-시클로프로필] 펜타-2,4-디엔아미드, (±)-(2E,4E) N-이소부틸-3-메틸-5-(트랜스-2-(3,5-비스트리 플루오로메틸-페닐)시클로프로필)-2,4-디엔아미드, (±)-(2E,4E) N-(1-2-디메틸프로필)-5-(트랜스-2-(3,5-비스트리 플루오로메틸프로필)시클로프로필)-2,4-디엔아미드, (±)-(2E,4E) N-(1-2-디메틸프로필)-5-(트랜스-2-(3,4-디클로로페닐)시클로프로필)-2,4-디엔아미드, (±)-(2E,4E) N-이소부틸-3-메틸-5-(트랜스-2-(3,4-디클로로페닐시클로프로필)-2,4-디엔아미드, (±)-(2E,4E) N-(1,2-디메틸프로필)-5(트랜스-2-(4-클로로페닐)시클로프로필)-2,4-디엔아미드, (±)-(2E,4E) N-(1,2-디메틸프로필)-5-[트랜스-2-(3,4-디블로모-페닐)시클로프로필]펜타-2,4-디엔아미드, (±)-(2E,4E) N-이소부틸-3-메틸-5-[트랜드-2-(3,4-디브로모-페닐)시클로프로필]펜타-2,4-디엔아미드, (±)-(2E,4E) N-(1,2-디메틸프로필)-5-[트랜스-2-(3-브로모-4-클로로페닐)시클로프로필]펜타-2,4-디엔아미드, (±)-(2E,4E) N-(1,2-디메틸프로필)-[r-1-플루오프-c-2-(3,4,5-트리클로로페닐)시클로프로필]펜타-2,4-디엔아미드, (±)-(2E,4E) N-이소부틸-3-메틸-5-[r-1-플루오로-c-2-(3,4,5-트리클로로페닐)시클로프로필]펜타-2,4-3-디엔아미드, (±)-(2Z,4E) N-이소부틸-2-플루오로-3-메틸-5-[트랜스-2-(3,4-디클로로페닐)시클로프로필]펜타-2,4-디엔아미드, (±)-(2Z,4E) N-(2-메틸프로필-2-에닐)-2-에닐)-2-플루오로-3-메틸-5-(트랜스-2-(3,4-디클로로페닐)시클로프로필 펜타-2,4-디엔아미드, (±)-(2E,4E) N-(S-부틸)-5-[트랜스-2-(3,4-디클로로페닐)시클로프로필 펜타-2,4-디엔아미드, (±)-(2E,4E) N-(1,2-디메틸프로필)-5-[r-1-플로오로-c-2-(3,4-디클로로페닐)시클로프로필] 펜타-2,4-디엔아미드, (±)-(2E/Z,4E) N-(2-메틸프로프-2-에닐)-3-[r-1-플로오로-c-2-(3,4-디브로모페닐)시클로프로필] 펜타-2,4-디엔아미드, (±)-(2E/Z,4E) N-이소부틸-3-메틸-5-메틸-5-[r-1-플로오로-c-2-(3,4-디브로모페닐)시클로프로필] 펜타-2,4-디엔아미드, (±)-(2E/Z,4E) N-(1,2-디메틸프로필)-5-[r-1-플로오로-c-2-(3,4-디브로모페닐)시클로프로필] 펜타-2,4-디엔아미드, (±)-(2E/Z,4E) N-이소부틸-3-메틸-5-[r-1-플루오로-c-2-(3,4-디클로로페닐)시클로프로필] 펜타-2,4-디엔아미드, (±)-(2E/Z,4E) N-(1,2-디메틸프로필)-5-[r-1-클로로-c-2-(3,4-디클로로페닐)시클로프로필] 펜타-2,4-디엔아미드, (±)-(2E/Z,4E) N-(2-메틸프로로프-2-에닐)-3-메틸-4-플루오로-5-트랜스-2-(3,4-디클로로페닐)시클로프로필]펜타-2,4-디엔아미드, (±)-(2E/Z,4E) N-이소부틸-3-3메틸-[r-1-클로로-2-c-(3,4-디클로로페닐)시클로프로필]펜타-2,4-디엔아미드, (±)-(2E/Z,4E) N-(2-메틸프로프-2-에닐)-3-메틸-[r-1-플루오로-2-c-(3,4-디클로로페닐)시클로프로필]펜타-2,4-디엔아미드, (±)-(2E/Z,4E) N-(2-메닐프로프-2-에닐)-3-메틸-5-[r-1-플루오로-2-c-(3,4-5트리클로로페닐)시클로프로필]펜타-2,4-디엔아미드, (±)-(2E,4E) N-(2-메닐프로프-2-에닐)-3-메틸-5-[트랜스-2-(3,4-디브로모페닐)시클로프로필]펜타-2,4-디엔아미드로 부터 선택되는 화합물의 제조 방법.
  8. 제1항에 있어서, 상기(a)방법이 알데히드기 또는 케톤기를아미드/티오 아미드 말단부 또는 식(I)의 QQ1분절에 부착시키고 이어서 이것을 적당한 포스포러스 일리드와 반응시키는 것을 포함하는 방법.
  9. 제9항에 있어서, QQ1(CR2-CR3)COR4를 Z2CHR5(C=X)NHR1과 반응시키거나, QQ1COR2를 Z2CHR3CR4=(C=X)NHR1과 반응시키거나, 또는 QQ1(CR2=CR3)CHR4Z2를 R5CO=(C=X)NHR1과 반응시키거나, 또는 QQ1(CR2=CR3)CHR4Z2를 방법.[상기식중, Q,Q1,X 및 R1내지 R5는 상기 식(I)에서 정의한 바와같이며, Z2는 (아릴)3P, (아릴)P(O) 또는 (C1-4알콕시)2PC(O)이다.
  10. 식 QQ1CR2=CR3CR4=CR5(=X)Z1, QQ1(CR2=CR3)COR4QQ1COR2또는 QQ1(CR2-CR3)CR4Z2의 신규 화학중간체.
  11. 제1항 내지 제8항중의 어느 한항에 기술된 식(I)의 화합물의 혼합도니 담체 또는 희석제를 포함하는 살충 또는 진드기 구제 조성물.
  12. 식(I)의 화합물 및 담체 또는 희석제의 상승 작용을 위해 제1항 내지 제8항중 어느 한항에 기술된 식(I)의 화합물을 포함하는 상승 작용된 살충 조성물.
  13. 제1항 내지 제8항중의 어느 한항에 기술된 식(I)의 화합물과 다른 살충 화합물의 혼합물.
  14. 제1항 내지 제8항중의 어느 한항에 기재된 화합물 또는 제11항 내지 제13항중의 어느 한항에 기재된 조성물 또는 혼합물을 해충 또는 해충 전염에 민감한 환경에 적용되는 것을 포함하는 해충의 구제 방법.
  15. 인체 또는 동물에서 행하는 외과 수술 또는 치료 방법, 또는 인체 또는 동물에서 행하는 진단 방법에 유용한 제1항 내지 제8항중의 어느 한항에 기재된 화합물 또는 제11항 내지 제13항중의 어느 한항에 기재된 조성물.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019890016642A 1988-11-16 1989-11-15 살충제 KR0140890B1 (ko)

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US6403638B1 (en) 1998-10-01 2002-06-11 Allergan Sales, Inc. 2,4-pentadienoic acid derivatives having selective activity for retinoid X (RXR) receptors
US6147224A (en) * 1998-10-01 2000-11-14 Allergan Sales, Inc. 2,4-pentadienoic acid derivatives having selective activity for retinoid X (RXR) receptors
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IL92317A0 (en) 1990-07-26
BR8905808A (pt) 1990-06-12
DE68911876T2 (de) 1994-05-05
ES2062036T3 (es) 1994-12-16

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