KR930000480A - 치환된 1h-3-아릴-피롤리딘-2,4-디온 유도체 - Google Patents

치환된 1h-3-아릴-피롤리딘-2,4-디온 유도체 Download PDF

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KR930000480A
KR930000480A KR1019920011297A KR920011297A KR930000480A KR 930000480 A KR930000480 A KR 930000480A KR 1019920011297 A KR1019920011297 A KR 1019920011297A KR 920011297 A KR920011297 A KR 920011297A KR 930000480 A KR930000480 A KR 930000480A
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피셔 라이너
크뤼거 베른트-빌란트
브레트쉬나이더 토마스
에르델렌 크리스토프
바헨도르프-노이만 울리케
뤼르쎈 클라우스
잔텔 한스-요아힘
아르. 쉬미트 로베르트
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Abstract

내용 없음

Description

치화된 1H-3-아릴-피롤리딘-2,4-디온 유도체
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (10)

  1. 일반식(I)의 치환된 3-아릴-피롤리딘-2,4-디온 유도체 및 일반식(I)의 화합물의 순수한 거울상 이성체 형태.
    상기 식에서, X는 알킬, 할로겐 또는 알콕시를 나타내고, Y는 수소, 알킬, 할로겐, 알콕시 또는 할로게노알킬을 나타내며, Z는 알킬, 할로겐 또는 알콕시를 나타내고, n은 0 내지 3의 숫자를 나타내며, A는 수소를 나타내거나, 또는 각각 임의로 할로겐으로 치환된 알킬, 알콕시알킬 또는 알킬티오알킬, 헤테로원자로 임의로 차단된 시클로알킬을 나타내거나, 또는 각각 할로겐, 알킬, 할로게노알킬, 알콕시 또는 니트로로 임의로 치환된 아릴, 아릴알킬 또는 헤트아릴을 나타내고, B는 수소, 알킬 또는 알콕시알킬을 나타내거나, 또는 A 및 B는 이들이 결합된 탄소원자와 함께, 임의로 치환된, 산소 및/또는 황으로 차단될 수 있는 포화 또는 불포화환을 형성하며, R은 일반식 (a), (b), (c) 또는 (d)로 표시되는 그룹을 나타내고,
    상기 식에서, L 및 M은 산소 또는 황을 나타내고, 단 L 및 M은 동시에 산소를 나타내지 않으며, R1, R2및 R3는 독립적으로 각각 임의로 할로겐 치환된 알킬, 알콕시, 알킬아미노, 디알킬아미노, 알킬티오, 알케닐티오, 알키닐티오 및 시클로알킬티오를 나타내고, 또한 각각 임의로 치환된 페닐, 벤질, 페녹시 또는 페닐티오를 나타내고, R4및 R5는 독립적으로 각각 수소를 나타내거나, 또는 각각 임의로 할로겐으로 치환된 알킬, 알케닐, 알콕시 또는 알콕시알킬을 나타내거나, 또는 임의로 치환된 페닐 또는 임의로 치환된 벤질을 나타내거나, 또는 R4및 R5는 함꼐 임의로 산소원자로 차단된 알케닐 라디칼을 나타내며, R6는 임의로 할로겐으로 치환되고, 산소로 차단될 수 있는 알킬을 나타내거나, 또는 임의로 할로겐, 할로게노알킬 또는 알콕시로 치환된 페닐을 나타내거나, 또는 임의로 할로겐, 할로게노느알킬, 알킬 및 알콕시로 치환된 벤질을 나타내거나, 또는 알케닐 또는 알키닐을 나타낸다.
  2. 일반식(Ia) 내지 (Id)의 치환된 3-아릴-피롤리딘-2,4-디은-유도체.
    상기 식에서, A, B, L, M, X, Y, Zn, R1, R2, R3, R4, R5및 R6는 특허청구범위 제1항에서 주어진 의미를 가진다.
  3. 제1항에 있어서, X가 C1-C6-알킬, 할로겐 또는 C1-C6-알콕시를 나타내고, Y가 수소, C1-C6-알킬, 할로겐 C1-C6-알콕시 또는 C1-C3-할로게노알킬을 나타내며, Z가 C1-C6-알킬, 할로겐 또는 C1-C6-알콕시를 나타내고, n이 0 내지 3의 숫자를 나타내며, A가 수소 또는 각각 임의로 할로겐으로 치환된, 각각 직쇄 또는 측쇄의 C1-C12-알킬, C3-C8-알케닐, C3-C8-알키닐, C1-C10-알콕시-C2-C8-알킬, C1-C8-폴리알콕시-C2-C8-알킬 및 C1-C10-알킬티오-C2-C8-알킬을 나타내거나, 또는 3 내지 8개의 환원자를 가지며, 산소 및/또는 황으로 차단될 수 있는 시클로 알킬을 나타내거나, 또는 각각 임의로 할로겐, C1-C6-알킬, C1-C6-할로알킬, C1-C6-알콕시 또는 니트로로 치환된 아릴, 헤트아릴 또는 아릴-C1-C6-알킬을 나타내고, B가 수소 또는 직쇄 또는 측쇄의 C1-C12-알킬 또는 C1-C8-알콕시알킬을 나타내거나, 또는 A 및 B가 이들이 결합된 탄소원자와 함께, 각각 임의로 할로겐화된 알킬, 알콕시 또는 페닐 및 할로겐으로 치환될 수 있고, 산소 및/또는 황으로 차단될 수 있는 3- 내지 8-원의 포화 또는 불포화환을 형성하며, R이 일반식 (a), (b), (c) 또는 (d)로 표시되는 그룹을 나타내고,
    L 및 M은 각각 산소 또는 황을 나타내고, 단 L 및 M은 동시에 산소를 나타내지 않으며, R1, R2및 R3가 개개 독립적으로 각각 임의로 할로겐 치환된 C1-C8-알킬, C1-C8-알콕시, C1-C8-알킬아미노, 디-(C1-C8)-알킬아미노, C1-C8-알킬티오, C2-C5-알케닐티오, C2-C5-알키닐티오 및 C3-C7-시클로알킬티오를 나타내거나, 또는 각각 임의로 할로겐, 니트로, 시아노, C1-C4-알콕시, C1-C4-할로게노알콕시, C1-C4-알킬티오, C1-C4-알로게노 알킬티오, C1-C4-알킬 또는 C1-C4-할로게노알킬로 치환된 페닐, 벤질, 페녹시 또는 페닐티오를 나타내고, R4및 R5가 개개 독립적으로 각각 임의로 할로겐 치환된 C1-C20-알킬, C1-C20-알콕시, C2-C8-알케닐 또는 C1-C20-알콕시-C1-C20-알킬을 나타내거나, 또는 임의로 할로겐, C1-C20-할로게노알킬, C1-C20-알킬 또는 C1-C20-알콕시로 치환된 페닐을 나타내거나, 또는 임의로 할로겐, C1-C20-알킬, C1-C20-할로게노알킬 또는 C1-C20-알콕시로 치환된 벤질을 나타내거나, 또는 R4및 R5가 함께 임의로 산소원자로 차단된 C2-C8-알킬렌환을 나타내며, R6가 임의로 할로겐으로 치환되고, 산소로 차단될 수 있는 C1-C20-알킬을 나타내거나, 또는 임의로 할로겐, C1-C20-할로게노알킬 또는 C1-C20-알콕시로 치환된 페닐을 나타내거나, 임의로 할로겐, C1-C20-할로게노알킬 또는 C1-C20-알콕시로 치환된 벤질을 나타내거나, 또는 C2-C8-알케닐 또는 C2-C5-알키닐을 나타내는 일반식(I)의 치환된 3-아릴-피롤리딘-2,4-디온유도체 및 일반식(I)의 화합물의 순수한 거울상 이성체 형태.
  4. 제1항에 있어서, X가 C1-C6-알킬, 할로겐 또는 C1-C6-알콕시를 나타내고, Y가 수소, C1-C6-알킬, 할로겐 C1-C4-알콕시 또는 C1-C2-할로게노알킬을 나타내며, Z가 C1-C4-알킬, 할로겐 또는 C1-C4-알콕시를 나타내고, n이 0 내지 3의 숫자를 나타내며, A가 수소 또는 각각 임의로 할로겐으로 치환된, 각각 직쇄 또는 측쇄의 C1-C20-알킬, C3-C8-알케닐, C3-C8-알키닐, C1-C8-알콕시-C2-C8-알킬, C1-C8-폴리알콕시-C2-C8-알킬 및 C1-C8-알킬티오-C2-C8-알킬을 나타내거나, 또는 3 내지 7개의 환원자로 가지며, 1내지 2개의 산소 및/또는 황원자로 차단될 수 있는 시클로 알킬을 나타내거나, 또는 각각 임의로 할로겐, C1-C4-알킬, C1-C4-할로알킬, C1-C4-알콕시 또는 니트로로 치환된 아릴, 헤트아릴 또는 아릴-C1-C4-알킬을 나타내고, B가 수소 또는 직쇄 또는 측쇄의 C1-C10-알킬 또는 C1-C6-알콕시알킬을 나타내거나, 또는 A 및 B가 이들이 결합된 탄소원자와 함께, C1-C6-알킬, C1-C6-알콕시, C1-C3-할로알콕시, 불소, 염소 및 치환된 페닐로 치환될 수 있고, 산소 및/또는 황으로 차단될 수 있는 3- 내지 7-원의 포화 또는 불포화환을 형성하며, R이 일반식 (a), (b), (c) 또는 (d)로 표시되는 그룹을 나타내고,
    상기식에서 L 및 M은 각각 산소 또는 황을 나타내고, 단 L 및 M은 동시에 산소를 나타내지 않으며, R1, R2및 R3가 개개 독립적으로 각각 임의로 할로겐 치환된 C1-C6-알킬, C1-C6-알콕시, C1-C6-알킬아미노, 디-(C1-C8)-알킬아미노, C1-C8-알킬티오, C3-C4-알케닐티오, C3-C4-알키닐티오 및 C3-C6-시클로알킬티오를 나타내거나, 또는 각각 임의로 불소, 염소, 브롬, 니트로, 시아노, C1-C3-알콕시, C1-C3-알로게노알콕시, C1-C3-알킬티오, C1-C3-알로게노 알킬티오, C1-C3-알킬 또는 C1-C3-할로게노알킬로 치환된 페닐, 벤질, 페녹시 또는 페닐티오를 나타내고, R4및 R5가 개개 독립적으로 각각 임의로 할로겐 치환된 C1-C20-알킬, C1-C20-알콕시, C2-C8-알케닐 또는 C1-C20-알콕시-C1-C20-알킬을 나타내거나, 또는 임의로 할로겐, C1-C5-알로게노알킬, C1-C5-알킬 또는 C1-C5-알콕시로 치환된 페닐을 나타내거나, 또는 임의로 할로겐, C1-C5-알킬, C1-C5-할로게노알킬 또는 C1-C5-알콕시로 치환된 벤질을 나타내거나, 또는 R6가 임의로 할로겐으로 치환되고, 산소로 차단될 수 있는 C1-C20-알킬을 나타내거나, 또는 임의로 할로겐, C1-C5-할로게노알킬 또는 C1-C5-알콕시로 치환된 페닐을 나타내거나, 임의로 할로겐, C1-C5-할로게노알킬 또는 C1-C5-알콕시로 치환된 벤질을 나타내는, 일반식(I)의 치환된 3-아릴-피롤리딘-2,4-디온유도체 및 일반식(I)의 화합물의 순수한 거울상 이성체 형태.
  5. 제1항에 있어서, X가 메틸, 에틸, 프로필, i-프로필, 불소, 염소, 브롬, 메톡시 및 에톡시를 나타내고, Y가 수소, 메틸, 에틸, i-프로필, 부틸, i-부틸, 3급-부틸, 불소, 염소, 브롬, 메톡시, 에톡시 및 트리플루오로 메틸을 나타내고, Z가 메틸, 에틸, i-프로필, 부틸, i-부틸, 3급-부틸, 불소, 염소, 브롬, 메톡시 및 에톡시를 나타내고, n이 0 내지 3의 숫자를 나타내고, A가 수소를 나타내거나, 또는 각각의 경우에서 각각 임의로 할로겐으로 치환된, 각각 직쇄 또는 측쇄의 C1-C8-알킬, C3-C4-알케닐, C3-C4-알키닐, C1-C6-알콕시-C2-C4-알킬, C1-C4-폴리옥콕시-C2-C4-알킬 및 C1-C6-알킬티오-C2-C4-알킬을 나타내거나, 또는 1 내지 2개의 산소 및/또는 황원자으로 차단될 수 있는 시클로 알킬을 나타내거나, 또는 각각 임의로 불소, 염소, 브롬, 메틸, 에틸, 프로필, i-프로필, 메톡시, 에톡시, 트리플루오로메틸 또는 니트로로 치환된 아릴, 피리딘, 이미다졸, 피라졸, 트리아졸, 인돌, 티아졸 또는 아릴-C1-C3-알킬을 나타내고, B가 수소 또는 각각의 경우에서 직쇄 또는 측쇄의 C1-C8-알킬 또는 C1-C4-알콕시알킬을 나타내거나, 또는 A 및 B가 이들이 결합된 탄소원자와 함께, C1-C4-알킬, C1-C4-알콕시, 트리플루오로메틸, 트리플루오로메톡시, 불소, 염소 및 치환된 페닐로 치환될 수 있고, 산소 및/또는 황으로 차단될 수 있는 3 내지 6원의 포화 또는 불포화환을 형성하며, R이 일반식 (a), (b), (c) 또는 (d)로 표시되는 그룹을 나타내고,
    상기식에서, L 및 M은 각각 산소 또는 황을 나타내고, 단 L 및 M은 동시에 산소를 나타내지 않으며, R1, R2및 R3가 개개 독립적으로 각각 임의로 불소 또는 염소로 치환된 C1-C4-알킬, C1-C4-알콕시, C1-C4-알킬아미노, 디-(C1-C4)아미노, 또는 C1-C4-알킬티오를 나타내거나, 또는 각각 임의로 불소, 브롬, 니트로, 시아노, C1-C2-알콕시, C1-C4-플루오로알콕시, C1-C2-클로로알콕시, C1-C2-알킬티오, C1-C2-플루오로 알킬티오, C1-C2-클로로알킬티오 또는 C1-C3-알킬로 치환된 페닐, 벤질, 페녹시 또는 페닐티오를 나타내고, R4및 R5가 개개 독립적으로 각각 임의로 불소, 염소 또는 브롬으로 치환된 C1-C10-알킬, C1-C10-알콕시, 또는 C1-C10-알콕시-(C1-C10)알킬을 나타내거나, 또는 임의로 불소, 염소, 브롬, C1-C20-할로게노알킬, C1-C20-알킬 또는 C1-C4-알콕시로 치환된 페닐을 나타내거나, 또는 임의로 불소, 염소, 브롬, C1-C4-알킬, C1-C4-할로게노알킬 또는 C1-C4-알콕시로 치환된 벤질을 나타내고, R6가 임의로 불소, 염소 또는 브롬으로 치환되고, 산소로 차단될 수 있는 C1-C120-알킬을 나타내거나, 또는 임의로 불소, 염소, 브롬, C1-C4-할로게노알킬 또는 C1-C4-알콕시로 치환된 페닐을 나타내거나, 임의로 불소, 염소, 브롬, C1-C4-할로게노알킬 또는 C1-C4-알콕시로 치환된 벤질을 나타내는 일반식(I)의 치환된 3-아릴-피롤리딘-2,4-디온유도체 및 일반식(I)의 화합물의 순수한 거울상 이성체 형태.
  6. (A)일반식(II)의 3-아릴-피롤리딘-2,4-디온 또는 그의 엔올을 경우에 따라 희석제의 존재하에서, 경우에 따라 산-결합제의 존재하에서 및 경우에 따라 상-이동 촉매의 존재하에서 일반식(III)인 인화합물과 반응시켜 일반식(Ia)의 치환된 3-아릴-피롤리딘-2,4-디온을 수득하거나, (B)일반식(II)의 화합물을 경우에 따라 희석제의 존재하에서 및 경우에 따라 산-결합제의 존재하에서 일반식(IV)의 술포닐클로라이드와 반응시켜 일반식(Ib)의 화합물을 수득하거나, (C)일반식(II)의 화합물을 α)경우에 따라 희석제의 존재하에서 및 경우에 따라 촉매의 존재하에서 일반식(V)의 이소시아네이트와 반응시키거나, β)경우에 따라 희석제의 존재하에서 및 경우에 따라 산-결합제의 존재하에서 일반식(VI)의 카르밤산클로라이드 또는 티오카르밤산 클로라이드와 반응시켜, 일반식(Ic)의 화합물을 α)경우에 따라 희석제의 존재하에서 및 경우에 따라 산-결합제의 일반식(VII)의 클로로 모노티오포름산 에스테르, 클로로포름산티오에스테르 또는 클로로디티오포름산 에스테르와 반응시키거나, β)이황화탄소와 반응시키고, 계속해서 일반식(VIII)의 알킬할라이드와 반응시켜, 일반식(Id)의 화합물을 수득함을 특징으로 하여 일반식(I)의 치환된 3-아릴-피롤리딘-2,4-디온 유도체를 제조하는 방법.
    상기 식에서, X는 알킬, 할로겐 또는 알콕시를 나타내고, Y는 수소, 알킬, 할로겐, 알콕시 또는 할로게알킬을 나타내며, Z는 알킬, 할로겐 또는 알콕시를 나타내고, n은 0 내지 3의 숫자를 나타내며, A는 수소를 나타내거나, 또는 각각 임의로 할로겐으로 치환된 알킬, 알콕시알킬 또는 알킬티오알킬, 헤테로원자로 임의로 차단된 시클로알킬을 나타내거나, 또는 각각 할로겐, 알킬, 할로게노알킬, 알콕시 또는 니트로로 임의로 치환된 아릴, 아릴알킬 또는 헤트아릴을 나타내고, B는 수소, 알킬 또는 알콕시알킬을 나타내거나, 또는 A 및 B는 이들이 결합된 탄소원자와 함께, 임의로 치환된, 산소 및/또는 황으로 차단될 수 있는 포화 또는 불포화환을 형성하며, R은 일반식 (a),(b),(c)또는 (d)로 표시되는 그룹을 나타내고,
    상기 식에서, L 및 M은 산소 또는 황을 나타내고, 단 L 및 M은 동시에 산소를 나타내지 않으며, R1, R2및 R3는 독립적으로 각각 임의로 할로겐 치환된 알킬, 알콕시, 알킬아미노, 디알킬아미노, 알킬티오, 알케닐티오, 알키닐티오 및 시클로알킬티오를 나타내고, 또한 각각 임의로 치환된 페닐, 벤질, 페녹시 또는 페닐티오를 나타내고, R4및 R5는 독립적으로 각각 수소를 나타내거나, 또는 각각 임의로 할로겐으로 치환된 알킬, 알케닐, 알콕시 또는 알콕시알킬을 나타내거나, 또는 임의로 치환된 페닐 또는 임의로 치환된 벤질을 나타내거나, 또는 R4및 R5는 함께 임의로 산소원자로 차단된 알케닐 라디칼을 나타내며, R6는 임의로 할로겐으로 치환되고, 산소로 차단될 수 있는 알킬을 나타내거나, 또는 임의로 할로겐, 할로게노알킬 또는 알콕시로 치환된 페닐을 나타내거나, 또는 임의로 할로겐, 할로게노알킬, 알킬 및 알콕시로 치환된 벤질을 나타내거나, 또는 알케닐 또는 알키닐을 나타내고, 일반식(III)에서 Hal은 할로겐, 특히 염소 및 브롬을 나타내며, 일반식(VIII)에서 Hal은 염소, 브롬 또는 요오드를 나타낸다.
  7. 적어도 하나의 일반식(I)의 3-아릴-피롤리딘-2,4-디온 유도체를 함유함을 특징으로 하는 살충, 살비 및 제초제.
  8. 일반식(I)의 3-아릴-피롤리딘-2,4-디온 유도체를 곤충 및/또는 진드기 및/또는 잡초 및/또는 이들의 환경에 적응시킴을 특징으로 하는 곤충 및/또는 진드기 및/또는 잡초를 구제하는 방법.
  9. 곤충 및/또는 진드기 및/또는 잡초를 구제하기 위한 일반식(I)의 3-아릴-피롤리딘-2,4-디온 유도체의 용도.
  10. 일반식(I)의 3-아릴-피롤리딘-2,4-디온 유도체를 중량제 및/또는 계면활성제와 혼합함을 특징으로 하여 살충 및/또는 살비 및/또는 제초제를 제조하는 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019920011297A 1991-06-28 1992-06-26 치환된 1h-3-아릴-피롤리딘-2,4-디온 유도체 Expired - Fee Related KR100231804B1 (ko)

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CA2072280A1 (en) 1992-12-29
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ZA924746B (en) 1993-03-31
US5616536A (en) 1997-04-01
DE4121365A1 (de) 1993-01-14
ES2120424T3 (es) 1998-11-01
EP0521334B1 (de) 1998-09-09
MX9203644A (es) 1993-11-01
JPH05221971A (ja) 1993-08-31
US5589469A (en) 1996-12-31
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DE59209490D1 (de) 1998-10-15
KR100231804B1 (ko) 2000-02-01

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