KR910004541A - 제초제 글루타람산 및 그 유도체 - Google Patents

제초제 글루타람산 및 그 유도체 Download PDF

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KR910004541A
KR910004541A KR1019900013703A KR900013703A KR910004541A KR 910004541 A KR910004541 A KR 910004541A KR 1019900013703 A KR1019900013703 A KR 1019900013703A KR 900013703 A KR900013703 A KR 900013703A KR 910004541 A KR910004541 A KR 910004541A
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South Korea
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alkyl
hydrogen
compound
alkoxycarbonyl
carboxy
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KR1019900013703A
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English (en)
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클리포드 레인지 배리
위싱거 코닐 제인
윌리엄 애쉬모어 죤
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원본미기재
롬 앤드 하스 캄파니
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Publication of KR910004541A publication Critical patent/KR910004541A/ko

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
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    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
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    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C233/07—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
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    • C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
    • C07C233/15—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
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    • C07C233/25—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
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Abstract

내용 없음.

Description

제초제 글루타람산 및 그 유도체
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (28)

  1. 다음 일반식 I의 글루타람산 화합물
    상기 일반식 I에서, A는 히드록시메틸, 클로로메틸, 카르복시, 카르복시염(CO2 -M+, 여기서 M+는 농경학적으로 허용되는 염임), 알콕시 카보닐, 또는 알킬아미노카보닐이고 ; D는 CH 또는 N이고 ; n은 0 또는 1이고 ; R은 수소, (C1-C4)알킬, 1개 내지 9개의 할로겐 원자를 함유하는 할로(C1-C4)알킬 또는 페닐이고 ; R1은 수소, (C1-C2)알킬 또는 할로(C1-C2)알킬이고 ; R2는 수소 또는 (C1-C2)알킬이고 ; T는 수소 또는 불소이고 ; X는 수소 또는 할로겐이고 ; Y는 수소, 할로(C1-C3)알킬, (C1-C3)알킬, 시아노, 니트로, 할로겐, 페녹시 또는 페닐 티오이고 ; Z는 수소, 히드록시, 할로겐, 알콕시, 알케닐옥시, 알키닐옥시, 알킬티오, 알케닐티오, 알키닐티오, 카르복시알콕시, 카르복시알킬티오, 알콕시카보닐알콕시, 알콕시카보닐알킬티오, 시클로알콕시, 시클로알킬알콕시, 시클로알킬티오, 시클로알킬알킬디오, 헤테로고리알콕시, 포르밀, 알카노일, 알콕시카보닐, 알케닐옥시카보닐, 알키닐옥시카보닐, 시클로알콕시카보닐, 시클로알킬알콕시카보닐, 알콕시카보닐 알콕시카보닐, 알킬, 히드록시알킬, 알콕시알킬, 알케닐옥시알킬, 알키닐옥시알킬, 알킬티오알킬, 알케닐티오알킬, 알키닐티오알킬, 시클로알콕시알킬, 시클로알킬알콕시알킬, 시클로알킬티오알킬, 시클로알킬알킬티오알킬, 알콕시카보닐, 알콕시알킬, 페녹시알킬, 페닐티오알킬, 알킬아미노알킬, 헤테로고리, 옥시밀(-CH=NOH), 알킬옥시밀, 알케닐옥시밀, 알키닐오시밀, 알콕시카보닐알킬옥시밀, 알킬(알킬)옥시밀, 알케닐(알킬)옥시밀, 알키닐(알킬)옥시밀, 알콕시카보닐알킬(알킬)옥시밀, 알킬아미노, 모노알케닐아미노, 모노알키닐아미노, 알킬술포닐아미노 또는 알카노일아미노 이며 ; 또는 Y와 Z는 함께 다음 구조식의 이중고리를 형성하도록 페닐 고리에 연합되는 헤테로고리를 형성할 수 있으며 ;
    상기 구조식들에서, L은 산소 또는 황이고 ; R3은 수소 또는 알킬이며 ; R4는 수소, 알킬, 알케닐, 알키닐, 알콕시알킬, 알케닐옥시알킬, 알키닐옥시알킬, 알콕시카보닐알킬, 시클로알킬, 시클로알킬알킬, 페닐알킬, 알킬리오알킬, 알케닐티오알킬, 알키닐티오알킬, 헤테로고리알킬, 알킬아미노알킬, 알콕시카보닐 또는 알카노일임.
    X와 Z가 각각 수소 또는 할로겐이고, Y가 할로겐이며, D가 CH인 경우, R은 반드시 트리플루오로메틸(CF3)이고 ; Y가 수소이고, R이 트리플루오로메틸인 경우, R1과 R2는 수소이고 Z는 수소가 아니고 ; Y가 염소이고 Z가 산소에 의하여 페닐고리에 연결된 치환체인 경우, R은 수소가 아니고 ; Z가 아세트아미도인 경우, Y는 염소가 아니다.
  2. 제1항에 있어서, 일반식 I에서의 각 치환체들이 다음과 같은 글루타람산의 화합물. A는 CH2OH, CH2Cl, COOH, COO-M+(M+는 농경학적으로 허용되는 염임), (C1-C6)알콕시카보닐 또는 (C1-C6)알킬아미노카보닐이고 ; n은 0이고, D는 CH 또는 N이고 ; R은 H, (C1-C4)알킬, 할로(C1-C4)알킬 또는 페닐이고 ; R1은 H 또는 (C1-C2)알킬이고 ; R2는 H 또는 (C1-C2)알킬이고 ; T는 H 또는 F이고 ; X는 H 또는 할로겐이고 ; Y는 수소, 할로겐 CF3, OC6H5, 시아노 또는 NO2이고 ; Z는 수소, 할로겐, (C1-C6)알콕시, (C3-C6)알케닐옥시, 할로(C3-C6)알케닐옥시, (C3-C6)알키닐옥시, (C3-C6)알킬티오, (C3-C6)알케닐티오, (C3-C6)알키닐티오, 페닐(C1-C6)알콕시, 헤테로고리(C1-C6)알콕시, 페닐(C1-C6)알킬티오, 카르복시(C1-C6)알킬티오, (C1-C6)알콕시카보닐(C1-C6)알킬티오, (C1-C6)알카노일, (C1-C6)알콕시카보닐, (C1-C6)알킬, 히드록시(C1-C6)알킬, (C1-C6)알콕시(C1-C6)알킬, (C3-C6)알케닐옥시(C1-C6)알킬, (C3-C6)알키닐옥시(C1-C6)알킬, (C1-C6)알킬티오(C1-C6)알킬, (C1-C6)알콕시카보닐(C1-C6)알콕시(C1-C6)알킬, 페녹시(C1-C6)알킬, 페닐티오(C1-C6)알킬, 헤테로고리, 디(C1-C6)알킬아미노(C1-C6)알킬, 모노(C1-C6)알카노일아미노, 또는 디(C1-C6)알킬술포닐아미노이며 ; 또는 Y와 Z는 함께 다음 구조식의 이중 고리를 형성하도록 페닐 고리에 연합되는 헤테로고리를 형성할 수 있으며 ;
    상기 구조식들에서, L은 산소 또는 황이고 ; R3은 수소 또는 (C1-C3)알킬이고, R4는 수소, (C1-C6)알킬, (C3-C6)알케닐, 할로(C3-C6)알케닐, (C3-C6)알키닐, (C3-C6)시클로알킬(C1-C6)알킬, (C1-C6)알콕시(C1-C6)알킬, 페닐(C1-C6)알킬, 시아노(C1-C6)알킬, 헤테로고리(C1-C6)알킬, (C1-C6)알킬아미노(C1-C6)알킬, 또는 (C1-C6)알콕시카보닐(C1-C6)알킬임. X와 Z가 각각 수소 또는 할로겐이고, Y가 할로겐이며, D가 CH인 경우, R은 반드시 CF3이고 ; Y가 수소이고 R이 트리플루오로메틸(CF3)인 경우, R1과 R2는 수소이고 Z는 수소가 아니고 ; Y가 염소(C1)이고 Z가 산소에 의하여 페닐고리에 연결된 치환체인 경우, R은 수소가 아니며 ; Z가 아세트아미도인 경우, Y는 염소가 아니다.
  3. 제2항에 있어서, 일반식 I에서의 각 치환체들이 다음과 같은 화합물.
    A는 CO2H, (C1-C6)알콕시카보닐 또는 CO2 -M+이고 ; D는 CH 또는 X가 H인 경우에는 N이고 ; n은 O이고 ; R은 (C1-C4)알킬 또는 할로(C1-C4)알킬이고 ; R1은 H 또는 (C1-C2)알킬이고 ; R2는 H이고 ; X는 수소 또는 할로겐이고 ; Y는 수소 또는 할로겐이고 ; T는 H 또는 F이고 ; Z는 H, (C1-C6)알콕시, (C1-C6)알케닐옥시, 할로(C3-C6)알케닐옥시, (C3-C6)알키닐옥시, (C1-C6)알킬티오, (C3-C6)알케닐티오, (C3-C6)알키닐티오, 페닐(C1-C6)알콕시, 헤테로고리(C1-C6)알콕시, 페닐(C1-C6)알킬티오, 카르복시(C1-C6)알킬티오, 또는 (C1-C6)알콕시카보닐(C1-C6)알킬티오임.
  4. 제3항에 있어서, A는 카르복시, (C1-C6)알콕시카보닐 또는 CO2 -M+이고 ; D는 CH이고 ; n은 0이고 ; R은 CH3, CF3, CHF2또는 CF2CF3이고 ; R1은 H이고 ; X는 Cl 또는 F이고 ; Y는 Br, F 또는 Cl이고 ; T는 H이고 ; Z는 (C1-C6)알콕시, (C3-C6)알케닐옥시 또는 (C3-C6)알키닐옥시인 것을 특징으로 하는 화합물.
  5. 제4항에 있어서, A는 카르복시, 에톡시카보닐, 메톡시카보닐, 이소프로필옥시카보닐, 에토민카르복실레이트, 이소프로필 암모늄카르복실레이트 또는 칼륨 카르복실레이트이고 ; X는 F이고 ; Y는 Br 또는 Cl이고 ; Z는 프로파길옥시, 알릴옥시, n-프로필옥시, 이소프로필옥시, 에톡시 또는 메톡시인 것을 특징으로 하는 화합물.
  6. 제5항에 있어서, A는 카르복시이고 ; R은 CF3이고 ; Y는 Cl이고 ; Z는 프로파길옥시, 이소프로파길옥시, n-프로필옥시, 에톡시, 메톡시 또는 알릴옥시인 것을 특징으로 하는 화합물.
  7. 제5항에 있어서, R은 CH3이고 ; A는 COOH이고 ; Y는 Cl 또는 Br이며 ; Z는 프로파길옥시인 것을 특징으로 하는 화합물.
  8. 제5항에 있어서, R은 CF2CF3이고 ; A는 COOH이며 ; Z는 프로파길옥시인 것을 특징으로 하는 화합물.
  9. 제5항에 있어서, R은 CF3이고 ; Y는 Cl이고 ; Z는 프로파길옥시이며 ; A는 카르복시, 에톡시카보닐, 메톡시카보닐, 이소프로필옥시카보닐, 에토민카르복실레이트, 이소프로필암모늄 카르복실레이트 또는 칼륨카르복실레이트인 것을 특징으로 하는 화합물.
  10. 제5항에 있어서, R은 CHF2이고 ; Y는 Cl이고 ; Z는 프로파길옥시이며 ; A는 카르복시인 것을 특징으로 하는 화합물.
  11. 제5항에 있어서, R은 CF3이고 ; Y는 Cl이고 ; Z는 이소프로필옥시이며 ; A는 카르복시 또는 메톡시 카보닐인 것을 특징으로 하는 화합물.
  12. 제2항에 있어서, A는 카르복시이고 ; D는 CH 또는 X가 H인 경우에는 N이고 ; n은 0이고 ; R은 (C1-C4)알킬 또는 할로(C1-C4)알킬이고 ; R1은 H 또는 (C1-C2)알킬이고 ; R2는 H이고 ; X는 H 또는 할로겐이고 ; Y는 H 또는 할로겐이고 ; T는 H 또는 F이며 ; Z는 (C1-C6)알콕시카보닐인 것을 특징으로 하는 화합물, 및 농경학적으로 허용되는 그 염.
  13. 제12항에 있어서, A는 카르복시이고 ; D는 CH이고 ; R은 CH3, CF3또는 CHF2이고 ; R1항에 있어서,은 H이고 ; X는 Cl 또는 F이고 ; Y는 Br, F 또는 Cl이고 ; T는 H이며 ; Z는 (C1-C6)알콕시카보닐인 것을 특징으로 하는 화합물.
  14. 제13항에 있어서, R은 CF3이고 ; X는 F이고 ; Y는 Cl 또는 Br이고 ; Z는 이소프로필옥시카보닐인 것을 특징으로 하는 화합물.
  15. 제13항에 있어서, R은 CHF2또는 CH3이고 ; X는 F이고 ; Y는 Cl이며 ; Z는 이소프로필옥시카보닐인 것을 특징으로 하는 화합물.
  16. 제2항에 있어서, A는 카르복시이고 ; D는 CH 또는, X가 H인 경우에는 N이고 ; n은 0이고 ; R은 (C1-C4)알킬 또는 할로(C1-C4)알킬이고 ; R1은 H 또는 (C1-C2)알킬이고 ; R2는 H이고 ; X는 H 또는 할로겐이고 ; Y는 H 또는 할로겐이고 ; T는 H 또는 F이며 ; Z는 (C1-C6)알콕시(C1-C6)알킬, (C3-C6)알케닐옥시(C1-C6)알킬 또는 (C3-C6)알키닐(C1-C6)알킬인 것을 특징으로 하는 화합물 및 농경학적으로 허용되는 그 염.
  17. 제16항에 있어서, A는 카르복시이고 ; D는 CH이고 ; n은 0이고 ; R은 CF3이고 ; R1은 H이고 ; X는 Cl 또는 F이고 ; Y는 Br, F 또는 Cl이고 ; T는 H이며 ; Z는 (C1-C6)알콕시(C1-C6)알킬, (C3-C6)알케닐옥시(C1-C6)알킬 또는 (C3-C6)알킬닐옥시(C1-C6)알킬인 것을 특징으로 하는 화합물.
  18. 제17항에 있어서, X는 F이고 ; Y는 Cl이며 ; Z는 이소프로필옥시메틸 또는 1-메틸프로파길옥시메틸인 것을 특징으로 하는 화합물.
  19. 제2항에 있어서, Y와 Z가 함께 하기 구조식의 헤테로고리를 형성하며 각 치환체가 다음과 같은 화합물.
    A는 COOH, (C1-C6)알콕시카보닐 또는 COO-M+이고 ; D는 CH이고 ; n은 0이고 ; L은 산소 또는 황이고 ; X는 수소 또는 불소이고 ; R은 (C1-C4)알킬 또는 할로(C1-C4)알킬이고 ; R1은 H 또는 (C1-C2)알킬이고 ; R2는 수소이고 ; R3은 수소 또는 (C1-C3)알킬이며 ; R4는 수소, (C1-C6)알킬, (C3-C6)알케닐, 할로(C3-C6)알케닐, (C3-C6)알키닐, (C3-C6)시클로알킬(C1-C6)알킬, (C1-C6)알콕시(C1-C6)알킬, 페닐(C1-C6)알킬, 시아노(C1-C6)알킬, 헤테로고리(C1-C6)알킬, (C1-C6)알킬아미노(C1-C6)알킬 또는 (C1-C6)알콕시카보닐(C1-C6)알킬임.
  20. 제19항에 있어서, 다음 일반식을 갖는 화합물.
    상기 일반식에서, A는 카르복시, COO-M+또는 (C1-C6)알콕시카보닐이고 ; X는 H 또는 F이고 ; L은 0 또는 S이고 ; R은 CH3, CF2H 또는 CF3이고 ; R3은 H 또는 (C1-C3)알킬이며 ; R4는 (C1-C6)알킬, (C3-C6)알케닐, 할로(C3-C6)알케닐, (C3-C6)알키닐, (C3-C6)시클로알킬(C1-C6)알킬, (C1-C6)알콕시메틸, 시아노(C1-C6)알킬, 푸라닐(C1-C6)알킬 또는 페닐(C1-C6)알킬임.
  21. 제20항에 있어서, 다음 일반식을 갖는 화합물.
    상기 일반식에서, A는 카르복시이고 ; L은 산소이고 ; X는 H 또는 F이고 ; R은 CF3또는 CHF2이고 ; R3은 메틸이며 ; R4는 프로파길임.
  22. 제20항에 있어서, A는 카르복시 또는 알콕시카보닐이고 ; L은 산소이고 ; X는 H 또는 F이고 ; R은 CF3또는 CHF2이고 ; R3은 수소이고 ; R4는 프로파길, 에틸, 알릴, 2-메틸알릴, 2-클로로알릴, 시클로프로필메틸, n-프로필, 이소프로필, 이소부틸, 2-테트라하이드로푸라닐메틸, 시아노메틸, 에톡시메틸, 메톡시메틸 또는 2-부테닐인 것을 특징으로 하는 화합물.
  23. 제22항에 있어서, A는 카르복시이고 ; L은 산소이고 ; X는 수소이고 ; R은 CF3이고 ; R3은 수소이며 ; R4는 프로파길, 알릴 또는 메톡시메틸인 것을 특징으로 하는 화합물.
  24. 제22항에 있어서, A는 카르복시이고 ; L은 산소이고 ; X는 F이고 ; R은 CF3이고 ; R3은 수소이며 ; R4는 프로파길, 에틸, 알릴, 2-메틸알릴, 2-클로로알릴, n-프로필, 이소프로필, 이소부틸, 시클로프로필메틸, 시아노메틸, 2-테트라하이드로푸라닐메틸, 메톡시메틸, 에톡시메틸 또는 2-부테닐인 것을 특징으로 하는 화합물.
  25. 제22항에 있어서, A는 메톡시카보닐 또는 이소프로필옥시카보닐 이고 ; L은 산소이고 ; X는 F이고 ; R은 CF3이고 ; R4는 H이며 ; R4는 알릴인 것을 특징으로 하는 화합물.
  26. 제22항에 있어서, A는 COO-NM4 +또는 COO-K+이고 ; L은 산소이고 ; X는 F이고 R3은 H이며 ; R4는 알릴인 것을 특징으로 하는 화합물.
  27. 제22항에 있어서, A는 COOH이고 ; R은 CHF2이고 ; L은 산소이고 ; X는 F이고 ; R3은 H이며 ; R4는 프로파길인 것을 특징으로 하는 화합물.
  28. 제20항에 있어서, 다음 일반식을 갖는 화합물.
    상기 일반식에서, A는 COOH이고 ; X는 H 또는 F이며 ; R4는 프로파길임.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019900013703A 1989-08-31 1990-08-31 제초제 글루타람산 및 그 유도체 KR910004541A (ko)

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JPH08151364A (ja) * 1994-02-18 1996-06-11 Nissan Chem Ind Ltd 含窒素環状化合物および除草剤
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UA89941C2 (ru) 2002-10-30 2010-03-25 Басф Акциенгезелльшафт Фенилизо(тио)цианаты и промежуточные соенинения, способы их получения
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WO2009050120A1 (de) * 2007-10-12 2009-04-23 Basf Se Verfahren zur herstelung von sulfonsäurediamiden
CN103755658B (zh) * 2014-01-28 2016-06-01 迈克斯(如东)化工有限公司 苯并内酰胺化合物及其合成方法和应用
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CA2023495A1 (en) 1991-03-01
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