KR890005029A - (7-(헤테로)아릴옥시나프탈렌-2-일-옥시)알칸카복실산 유도체 - Google Patents

(7-(헤테로)아릴옥시나프탈렌-2-일-옥시)알칸카복실산 유도체 Download PDF

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KR890005029A
KR890005029A KR1019880012173A KR880012173A KR890005029A KR 890005029 A KR890005029 A KR 890005029A KR 1019880012173 A KR1019880012173 A KR 1019880012173A KR 880012173 A KR880012173 A KR 880012173A KR 890005029 A KR890005029 A KR 890005029A
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alkyl
halogen
group
hydrogen
optionally
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KR1019880012173A
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하우크 미카엘
안드레 롤란트
잔텔 한스-요아힘
에르. 쉬미트 로베르트
스트랭 해리
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귄터 슈마허, 클라우스 데너
바이엘 아크티엔게젤샤프트
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Publication of KR890005029A publication Critical patent/KR890005029A/ko

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    • C07D213/04Heterocyclic 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
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Abstract

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Description

(7-헤테로)아릴옥시나프탈렌-2-일-옥시)알칸카복실산 유도체
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (10)

  1. 다음 일반식(I)의 (7-헤테로)아릴옥시나프탈렌-2-일-옥시)알칸카복실산 유도체.
    상기식에서, R1은 할로겐, 시아노 또는 트리플루오로메틸이고, R2는 수소 또는 할로겐이며, R3은 할로겐, 트리플루오로메틸, 트리플루오로메톡시, 트리플루오로메틸티오 또는 트리플루오로메틸설포닐이고, R4는 수소 또는 할로겐이며, X는 질소 또는 그룹 C-R5(여기에서, R5는 수소 또는 할로겐이다)이고, 단 R1이 염소 또는 시아노이고, 동시에 R3은 트리플루오로메틸이며 X는 CH인 경우, 치환체 R2또는 R4중의 하나 이상은 수소가 아니며, X가 질소인 경우, R3은 트리플루오로메틸이 아니고, A는 임의 의 촉쇄 알칸디일이며, Z는 시아노 또는 그룹 -CO-Y[여기에서, Y는 할로겐, 하이드록실, 아미노, 알킬아미노, 알케닐아미노, 알키닐아미노, 아릴아미노, 아르알킬아미노, 알콕시카보닐알킬아미노, 시아노아미노, 디알킬아미노, 디알케닐아미노, N-알킬아릴아미노, 알킬설포닐아미노, 아릴설포닐아미노, 하이드록시아미노, 알콕시아미노, 하이드라지노, 알킬설포닐하이드라지노, 아릴설포닐하이드라지노, 알킬티오, 아릴티노, 아르알킬티오, 알콕시카보닐알킬티오 또는 그룹 -O-R6(여기에서, R6은 알킬, 알케닐, 알키닐, 알콕시알킬, 알킬티오알킬, 알킬설피닐알킬, 알킬설포닐알킬, 아릴옥시알킬, 아르알콕시알킬, 트리알킬실릴알킬, 아릴티오알킬, 아르알킬티오알킬, 알목시카보닐알킬, 알킬아미노카보닐알킬, 아릴아미노카보닐알킬, N-알킬-N-아릴아미노카보닐알킬, 아르알킬, 아졸릴알킬 및 알킬리덴아미노중에서 선택된 임의로 할로겐-치환된 라디칼이거나, 등가의 암모늄, 등가의 알킬암모늄, 등가의 알칼리금속 또는 등가의 알칼리 토금속이거나, 그룹(여기에서, R7은 수소, 알킬, 아릴, 푸릴, 티에닐 또는 피리딜이고, R8은 알킬 또는 알콕시이며, R9는 알콕시이고, Q는 산소 또는 황이다)이거나, 그룹 -(CH2)n-R10(여기에서, R10은 푸릴, 테트라히이드로푸릴, 옥소테트라하이드로푸릴, 티에닐, 테트라하이드로티에닐, 퍼하이드로피라닐, 옥사졸릴, 티아졸린, 티아디아졸린, 디옥솔라닐, 퍼하이드로피롤릴, 옥소퍼하이드로피롤릴, 피리디닐 및 피리미디닐중에서 선택된 임의로 할로겐-치환되고/되거나 임의로 알킬-치환된 헤테로사이클릭 라디칼이고, n은 0,1 또는 2이다)이다)이다]이다.
  2. 제1항에 있어서, R1은 불소, 염소, 브롬, 시아노 또는 트리플루오로메틸이고, R2는 수소, 불소 또는 염소이며, R3은 불소, 염소, 브롬, 트리플루오로메틸, 트리플루오로메톡시, 트리플루오로메틸티오 또는 트리플루오로메틸설포닐이고, R4는 수소, 불소 또는 염소이며, X는 질소 또는 그룹 C-R5(여기에서, R5는 수소, 불소, 염소 또는 브롬이다)이고, 단 R1이 염소 또는 시아노이고, 동시에 R3은 트리플루오로메틸이며 X는 CH인 경우, 치환체 R2또는 R4중의 하나 이상은 수소가 아니며, X가 질소인 경우, R3은 트리플루오로메틸이 아니고, A는 임의의 측쇄 C1-4알칸디일이며, Z는 시아노 또는 그룹 -CO-Y[여기에서, Y는 염소, 하이드록실, 아미노, C1-6알킬아미노, C3-4알케닐아미노, C3-4알키닐아미노, 페닐아미노, 벤질아미노, C1-4알콕시카보닐-C1-2알킬아미노, 시아노마이노, 디-(C1-4알킬) 아미노, 디-(C3-4알케닐)아미노, N-(C1-4알킬)페닐아미노, C1-4알킬설포닐아미노, 페닐설포닐아미노, 톨릴설포닐아미노, 하이드록시아미노, C1-6알콕시아미노, 하이드라지노, C1-4알킬설포닐하이드라지노, 페닐설포닐하이드라지노, 톨릴설포닐하이드라지노, C1-4알킬티오, 페닐티오, 벤질티오, C1-4알콕시카보닐-C1-2알킬티오 또는 그룹-O-R6(여기에서,R6은 C1-6알킬, C3-4알케닐, C3-4알키닐, C1-4알콕시-C1-4알킬, C1-4알킬티오-C1-4알킬, C14알킬설피닐-C1-4알킬, C1-4알킬설포닐-C1-4알킬, 페녹시-C1-3알킬, 트리-(C1-2알킬)실릴-C1-2알킬, 페닐티오-C1-3알킬, 벤질옥시-C1-3-알킬, 벤질티오-C1-3알킬, C1-4알콕시카보닐-C1-2알킬, C1-4알칼아미노카보닐-C1-2알킬, 페닐아미노카보닐-C1-4알킬, N-(C1-4알킬)-N-페닐아미노카보닐-C1-4알킬, 벤질, 피라졸릴-C1-4알킬 및 C2-4알킬덴아미노중에서 선택된 임의 로 불소-치환되고/되거나 임의 로 염소-치화뇐 라디칼이거나, 등가의 암모늄, 등가의 C1-4알킬암모늄, 등가의 나트륨, 등가의 칼륨 또는 등가의 칼슘이거나, 그룹(R7은 수소, C1-4알킬, 페닐, 푸릴, 티에닐 또는 피리딜이고, R8은 C1-4알콕시이며, R9는 C1-4알콕시이고, Q는 산소 또는 황이다)이거나, 그룹 -(CH2)n-R10(여기에서, n은 0,1 또는 2이고, R10은 불소, 염소 브롬 및/또는 C1-4알킬에 의해 임의 로 치환되며, 푸릴, 테트라히이드로푸릴, 옥소테트라하이드로푸릴, 티에닐, 테트라하이드로티에닐, 퍼하이드로피라닐, 옥사졸린, 티아졸린, 티아디아졸린, 디옥솔라닐, 퍼하이드로피롤릴, 옥소퍼하이드로피롤릴, 피리디닐 또는 피리미디닐중에서 선택된 헤테로사이클릭 라디칼이다)이다)이다)인 일반식(I)의 (7-헤테로)아릴옥시나프탈렌-2-일-옥시)알칸 카복실산 유도체.
  3. (a) 다음 일반식(II)의 7-(헤테로)아릴옥시-2-나프톨을, 경우에 따라 산 수용체의 존재하 및 경우에 따라 희석제의 존재하에, 다음 일반식(III)의 카복실산 유도체와 반응시키거나, (b) 다음 일반식(IV)의 할로게노-(헤테로)아릴화합물을, 경우에 따라 산 수용체의 존재하 및 경우에 따라 희석제의 존재하에, 다음 일반식(V)의 (7-하이드록시나프탈렌-2-일-옥시)알칸-카복실산 유도체와 반응시키거나, (c) 일반식(I)에서 Z가 그룹 -CO-Y(여기에서, Y는 하이드록실이다)이고, A, R1, R2, R3, R4및 X는 상기에서 정의한 바와 같은 경우, Z가 시아노 또는 그룹 -CO-Y(여기에서, Y는 메톡시 또는 에톡시이다)이고, A, R1, R2, R3, R4및 X는 상기에서 정의한 바와 같은 일반식(I)의 화합물을 유기용매의 존재하에 알칼리 금속수산화물과 반응시키고, 반응 혼합물을 농축시킨 다음, 경우에 따라, 무기산으로 산성화시키거나, (d) 일반식(I)에서 Z가 그룹 -CO-Y(여기에서, Y는 할로겐이다)이고, A, R1, R2, R3, R4 및 X는 상기에서 정의한 바와 같은 경우, Z가 그룹 -CO-Y(여기에서, Y는 하이드록실이다)이고, A, R1, R2, R3, R4및 X는 상기에서 정의한 바와 같은 일반식(I)의 화합물을, 경우에 따라 희석제의 존재하에 할로겐화제와 반응시키거나, (e) 일반식 (I)에서 Z가 그룹 -CO-Y(여기에서, Y는 할로겐을 제외한 상기에서 정의한 바와 같다)이고, A, R1, R2, R3, R4및 X는 상기에서 정의한 바와 같은 경우, Z가 시아노 또는 그룹 -CO-Y(여기에서, Y는 할로겐이다)이고, A, R1, R2, R3, R4및 X는 상기에서 정의한 바와 같은 일반식(I)의 화합물을, 경우에 다라 산 또는 산 수용체의 존재하 및 경우에 따라 희석제의 존재하에, 다음 일반식(VI)(여기에서, Y는 할로겐을 제외한 상기에서 정의한 바와 같다)의 화합물과 반응시키거나, (f) 일반식(I)에서 Z가 그룹 -CO-Y (여기에서, Y는 그룹 -O-R6(여기에서, R6은 암모늄, 알킬암모늄, 알칼리금속 및 알칼리토금속을 제외한 상기에서 정의한 바와 같다)이다)이고, A, R1, R2, R3, R4및 X는 상기에서 정의한 바와 같은 경우, Z가 그룹 -CO-Y(여기에서 Y는 하이드록실이다)이고, A, R1, R2, R3, R4및 X는 상기에서 정의한 바와 같은 일반식(I)의 화합물을, 경우에 따라 산 수용체의 존재하 및 경우에 따라 희석제의 존재하에, 다음 일반식(VII)의 화합물과 반응시킴을 특징으로 하여, 일반식(I)의 (7-헤테로)아릴옥시나프탈렌-2-일-옥시)알칸카복실산 유도체를 제조하는 방법.
    상기식에서, R1은 할로겐, 시아노 또는 트리플루오로메틸이고, R2는 수소 또는 할로겐이며, R3은 할로겐, 트리플루오로메틸, 트리플루오로메톡시, 트리플루오로메틸티오 또는 트리플루오로메틸설포닐이고, R4는 수소 또는 할로겐이며, X는 질소 또는 그룹 C-R5(여기에서, R5는 수소 또는 할로겐이다)이고, 단 R1이 염소 또는 시아노이고, 동시에 R3은 트리플루오로메틸이며 X는 CH인 경우, 치환체 R2또는 R4중의 하나 이상은 수소가 아니며, X가 질소인 경우, R3은 트리플루오로메틸이 아니고, A는 임의 의 촉쇄 알칸디일이며, Z는 시아노 또는 그룹 -CO-Y[여기에서, Y는 할로겐, 하이드록실, 아미노, 알킬아미노, 알케닐아미노, 알키닐아미노, 아릴아미노, 아르알킬아미노, 알콕시카보닐알킬아미노, 시아노아미노, 디알킬아미노, 디알케닐아미노, N-알킬아릴아미노, 알킬설포닐아미노, 아릴설포닐아미노, 하이드록시아미노, 알콕시아미노, 하이드라지노, 알킬설포닐하이드라지노, 아릴설포닐하이드라지노, 알킬티오, 아릴티노, 아르알킬티오, 알콕시카보닐알킬티오 또는 그룹 -O-R6(여기에서, R6은 알킬, 알케닐, 알키닐, 알콕시알킬, 알킬티오알킬, 알킬설피닐알킬, 알킬설포닐알킬, 아릴옥시알킬, 아르알콕시알킬, 트리알킬실릴알킬, 아릴티오알킬, 아르알킬티오알킬, 알목시카보닐알킬, 알킬아미노카보닐알킬, 아릴아미노카보닐알킬, N-알킬-N-아릴아미노카보닐알킬, 아르알킬, 아졸릴알킬 및 알킬리덴아미노중에서 선택된 임의로 할로겐-치환된 라디칼이거나, 등가의 암모늄, 등가의 알킬암모늄, 등가의 알칼리금속 또는 등가의 알칼리 토금속이거나, 그룹(여기에서, R7은 수소, 알킬, 아릴, 푸릴, 티에닐 또는 피리딜이고, R8은 알킬 또는 알콕시이며, R9는 알콕시이고, Q는 산소 또는 황이다)이거나, 그룹 -(CH2)n-R10(여기에서, R10은 푸릴, 테트라히이드로푸릴, 옥소테트라하이드로푸릴, 티에닐, 테트라하이드로티에닐, 퍼하이드로피라닐, 옥사졸릴, 티아졸린, 티아디아졸린, 디옥솔라닐, 퍼하이드로피롤릴, 옥소퍼하이드로피롤릴, 피리디닐 및 피리미디닐중에서 선택된 임의로 할로겐-치환되고/되거나 임의로 알킬-치환된 헤테로사이클릭 라디칼이고, n은 0,1 또는 2이다)이다)이다)이다. Z1은 친핵성 이탈기이며, Z2는 할로겐이고, R6-1은 암모늄, 알킬암모늄, 알칼리금속 및 알칼리토금속을 제외한 상기에서 R6엘 대하여 정의한 바와 같으며, Z3은 할로겐이다.
  4. 제1항 내지 제3항중 어느 한 항에 따른 일반식(I)의 (7-헤테로)아릴옥시나프탈렌-2-일-옥시)알칸카복실산 유도체를 하나 이상 함유함을 특징으로 하는 제초제.
  5. 제1항 내지 제3항중 어느 한 항에 따른 일반식(I)의 (7-헤테로)아릴옥시나프탈렌-2-일-옥시)알칸카복실산 유도체를 잡초 및/또는 이의 서식처에 작용시킴을 특징으로 하여, 잡초를 방제하는 방법.
  6. 잡초를 방제하기 위한, 제1항 내지 제3항중 어느 한 항에 따른 일반식(I)의 (7-헤테로)아릴옥시나프탈렌-2-일-옥시)알칸카복실산 유도체의 용도.
  7. 제1항 내지 제3항중 어느 한 항에 따른 일반식(I)의 (7-헤테로)아릴옥시나프탈렌-2-일-옥시)알칸카복실산 유도체를 중량제 및/또는 계면활성제와 혼합시킴을 특징으로 하여, 제초제를 제조하는 방법.
  8. 다음 일반식의 화합물.
  9. 다음 일반식(IIa)의 7-(헤테로)아릴옥시-2-나프톨.
    상기식에서, R1-1은 할로겐 또는 트리플루오로메틸이고, R2는 수소 또는 할로겐이며, R3은 할로겐, 트리플루오로메틸 또는 트리플루오로메톡시, 트리플루오로메틸티오 또는 트리플루오로메틸설포닐이고, R4는 수소 또는 할로겐이며, X1는 질소 또는 그룹 C-R5-1(여기에서, R5-1은 할로겐이다)이다.
  10. 다음 일반식(IVa)의 할로게노(헤테로(아릴 화합물을 산 수용체의 존재하 및 희석제의 존재하에 2,7-디하이드록시나프탈렌과 반응시킴을 특징으로하여, 다음 일반식(IIa)의 7-(헤테로)아릴옥시-2-나프톨을 제조하는 방법.
    상기 식에서, R1은 할로겐 또는 트리플루오로메틸이고, R2는 수소 또는 할로겐이며, R3은 할로겐, 트리플루오로메틸, 트리플루오로메톡시, 트리플루오로메틸티오 또는 트리플루오로메틸설포닐이고, R4는 수소 또는 할로겐이며, X1는 질소 또는 그룹 C-R5-1(여기에서5-1은 할로겐이다)이고, Z2는 할로겐이다.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019880012173A 1987-09-22 1988-09-21 (7-(헤테로)아릴옥시나프탈렌-2-일-옥시)알칸카복실산 유도체 KR890005029A (ko)

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DE19873731801 DE3731801A1 (de) 1987-09-22 1987-09-22 (7-(hetero)aryloxy-naphthalin-2-yl-oxy) -alkancarbonsaeure-derivate
DEP3731801.2 1987-09-22

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US (1) US5041609A (ko)
EP (1) EP0308755B1 (ko)
JP (1) JPH01113334A (ko)
KR (1) KR890005029A (ko)
AR (1) AR245696A1 (ko)
AU (1) AU624338B2 (ko)
DE (2) DE3731801A1 (ko)
DK (1) DK527188A (ko)
HU (1) HU200585B (ko)
ZA (1) ZA887045B (ko)

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Publication number Priority date Publication date Assignee Title
DE3737179A1 (de) * 1987-11-03 1989-05-18 Bayer Ag (6-(hetero)aryloxy-naphthalin-2-yl-oxy)-alkancarbonsaeure-derivate
DE4012711A1 (de) * 1990-04-21 1991-10-24 Bayer Ag Fluor-substituierte (alpha)-(5-aryloxy-naphthalin-l-yl-oxy)-propionsaeure-derivate
DE4111619A1 (de) * 1991-04-10 1992-10-15 Bayer Ag (alpha)-(5-aryloxy-naphthalin-1-yl-oxy)-carbonsaeure-derivate

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3434447A1 (de) * 1984-09-17 1986-03-27 Schering AG, 1000 Berlin und 4709 Bergkamen 7-(aryloxy)-2-naphthyloxy-alkancarbonsaeurederivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende mittel mit herbizider wirkung
AU570341B2 (en) * 1984-09-17 1988-03-10 Schering Aktiengesellschaft 7-(aryloxy)-2-naphthoxy alkanecarboxylic acid
EP0179015B1 (en) * 1984-09-17 1988-04-13 Schering Aktiengesellschaft 7-(aryloxy)-2-naphthoxyalkanecarboxylic acid derivatives, processes for the preparation of these compounds, as well as agents having herbicidal activity containing these compounds
JPS61165346A (ja) * 1985-01-16 1986-07-26 Mitsubishi Petrochem Co Ltd フエノキシナフトキシ酢酸誘導体及びこれを含有する除草剤
JPS6210041A (ja) * 1985-07-08 1987-01-19 Sumitomo Chem Co Ltd ナフトキシプロピオン酸誘導体、その製造法およびそれを有効成分とする除草剤
DE3737179A1 (de) * 1987-11-03 1989-05-18 Bayer Ag (6-(hetero)aryloxy-naphthalin-2-yl-oxy)-alkancarbonsaeure-derivate
DE3821389A1 (de) * 1988-06-24 1989-12-28 Bayer Ag 1,7-dioxy-naphthalin-derivate

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AU624338B2 (en) 1992-06-11
HU200585B (en) 1990-07-28
DK527188A (da) 1989-03-23
US5041609A (en) 1991-08-20
JPH01113334A (ja) 1989-05-02
DE3731801A1 (de) 1989-03-30
AR245696A1 (es) 1994-02-28
EP0308755A3 (en) 1989-07-26
EP0308755B1 (de) 1992-10-28
DE3875572D1 (de) 1992-12-03
ZA887045B (en) 1989-06-28
HUT47526A (en) 1989-03-28
DK527188D0 (da) 1988-09-22
AU2218188A (en) 1989-03-23
EP0308755A2 (de) 1989-03-29

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