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KR940005588A - 2-아릴피리미딘류 및 이의 제초성 용도 - Google Patents

2-아릴피리미딘류 및 이의 제초성 용도 Download PDF

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KR940005588A
KR940005588A KR1019930013396A KR930013396A KR940005588A KR 940005588 A KR940005588 A KR 940005588A KR 1019930013396 A KR1019930013396 A KR 1019930013396A KR 930013396 A KR930013396 A KR 930013396A KR 940005588 A KR940005588 A KR 940005588A
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alkenyl
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마이클 타이스 콜린
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윌리엄 이. 램버트 3세
롬 앤드 하스 캄파니
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Abstract

본 발명은 하기 일반식(Ⅰ)로 표시되는 잡초제거에 유용한 2-아닐피리미딘류를 제공한다.
상기식에서, R2는 임의로 치환된 방향족 그리고; R3는 포화 또는 불포화 알킬기이고; R5는 수소원자, 할로, 알킬, 알켄일, 알킨일, 알콕시 및 알킬티오기에서 선택된 기이고 R6는 수소원자, 할로, 알킬, 할로알킬, 아릴 및 알콕시기로부터 선택된 기이고; X는 산소원자 또는 황원자이다.
또한, 본 발명은 상기 화합물의 제초적으로 유효한 양을 잡초자체 또는 잡초 생장지역 또는 잡초의 생장매체에 살포하는 제초방법을 제공한다.

Description

2-아릴피리딘류 및 이의 제초성 용도
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (13)

  1. 일반식(Ⅰ)로 표시되는 화합물;
    상기식에서, (a) R2는 브로모, 클로로, 플루오로, (C1-C12)알킬, 시클로(C3-C8)알킬, (C2-C12)알켄일, 시클로(C3-C8)알켄일, (C2-C12)알킬, 폴리할로(C1-C12)알킬, 할로(C1-C12)알켄일, 폴리할로(C2-C12)알켄일, 할로(C2-C6)알킨일, 폴리할로(C2-C6)알킨일, (C1-C12)알콕시, (C1-C12)알킬티오(C1-C12)알킬술포닐, (C1-C12)알킬술포닐, 페닐, 펜(C1-C12)알킬, 펜(C2-C12)알켄일, 펜(C2-C12)알킨일, 시아노, 할로(C1-C12)알콕시, 1,3-디옥솔란-2-일, 히드록시이미노, 또는 니트로기에서 독립적으로 선택된 3이하의 치환체로 각기 임의로 치환된, 푸릴, 페닐, 나프틸, 피리딜, 또는 티에닐기이고; R2가 피리디일 경우, 이러한 피리딜기는 피리딜기의 질소원자상에 산소원자가 임의로 치환되거나; 또는 R2는 인접탄소원자 또는 푸릴, 페닐, 나프틸, 피리딜 또는 티에닐기에 옥시메틸렌옥시 또는 옥소에틸렌옥시 링크 결합을 이루는 접합고리 부분을 갖는 푸릴, 페닐 나프틸, 피리딜 또는 티에닐기이고; (b) R3는 (C1-C3)알킬; 할로(C1-C3)알킬, 폴리할로(C1-C3)알킬, (C3-C4)알켄일, (C5-C6)알켄인일, (C3-C6)알킨일, (C1-C6)알콕시(C1-C3)알킬, 디(C1-C6)알콕시(C1-C6)알킬, 할로(C1-C6)알콕시(C1-C6)알킬, 또는 2-옥소(C2-C6)알킬, 트리메틸실릴(C3-C4)알킨일 또는 시아노(C1-C6)알킬기이고, 상기 (C3-C4) 알켄일 또는 (C3-C6)알킨일기 각각은 5이하의 할로겐으로 임의로 치환되며; (c) R5는 수소원자, (C1-C5)알킬, (C3-C6)알켄일, (C2-C6)알킨일, 할로(C1-C6)알킬, 폴리할로(C1-C6)알킬, 할로(C2-C6)알켄일, 폴리할로(C2-C6)알켄일, 할로(C2-C6)알킨일, 폴리할로(C2-C6)알킨일, 할로(C1-C6)알콕시, 폴리할로(C1-C6)알콕시, 트리메실릴(C2-C3)알킨일, (C1-C6)알콕시, (C1-C6)알킬티오, (C1-C3)알콕시카르보닐(C1-C3)알킬, 할로 또는 시아노기이고; (d) R6는 수소원자, 할로겐원자, (C1-C8)알킬, (C2-C6)알켄일, (C2-C6)알킨일, 할로(C1-C6)알킬, 폴리할로(C1-C6)알킬, 할로(C2-C6)알켄일, 폴리할로(C2-C6)알켄일, 할로(C2-C6)알킨일, 폴리할로(C2-C6)알킨일, (C1-C6)알콕시, (C1-C6)알콕시(C1-C4)알킬, (C1-C6)알킬티오, (C1-C3)알콕시카르보닐, (C1-C3)알콕시카르보닐(C1-C3)알킬, (C6-C10)아릴, 아르(C1-C4)아릴, 시클로(C3-C7)알킬; 푸릴 피리딜 및 티에닐로 이루어진 군에서 선택된 (C4-C5)헤테로시클일, (C1-C3)알킬아미노, 디(C1-C3)알킬아미노카르보닐, 할로(C1-C6)알킬티오, 폴리할로(C1-C6)알킬티오, 할로(C1-C8)알콕시, 폴리할로(C1-C6)알콕시, (C6-C10)아릴옥시 또는 시아노기이고; 상기 (C6-C10)아릴, 아르(C1-C4)알킬 및 (C6-C10)아릴옥시기는 브르모, 클로로, 플루오로, (C1-C12)알킬, 시클로(C3-C8)알킬, (C2-C12)알켄일, 시클로(C2-C12)알켄일, 할로(C2-C12)알킨일, 할로(C1-C12)알킬, 폴리할로(C1-C12)알킬, 할로(C2-C12)알켄일, 폴리할로(C2-C12)알켄일, 할로(C2-C6)알킨일, 폴리할로(C2-C5)알킨일, (C1-C12)알콕시, (C1-C12)알킬티오, (C1-C12)알킬술폰일, (C1-C12)알킬술핀일, 페닐, 펜(C1-C12)알킬, 펜(C2-C12)알켄일, 펜(C2-C12)알킨일, 시아노, 할로(C1-C12)알콕시, 1, 3-디옥살란-2-일, 히드록시이미노 및 니트로기로부터 선택된 각기 3이하의 치환체로 임의로 치환되며; (e) X는 산소원자 또는 황원자이다.
  2. 제1항에 있어서, 상기 R2가 하기 (a), (b), (c) 및 (d)중 어느 하나인 것을 특징으로 하는 화합물; (a) 페닐, 3-메틸페닐, 3-메톡시페닐, 3-니트로페닐, 4-플루오로페닐, 4-클로로페닐, 3-트리플루오로메틸페닐, 3-브로모페닐, 3-클로로페닐, 3-플루오로페닐, 3-트리풀루오로메톡시페닐, 3-시아노페닐, 3-(1, 3-디옥솔란-2-일)-페닐, 3-(히드록시아노)페닐, 2-플루오로페닐, 2-클로로페닐, 2-트리플루오로메톡시페닐, 3,5-디플루오로페닐, 3,5-디클로로페닐, 2,4-디플루오로페닐, 2,5-디플루오로페닐, 3-클로로-4-플루오로페닐, 3,4-디플루오로페닐, 3-플루오로-5-트리플루오로메틸페닐, 또는 3,4,5-트리플루오로페닐기; (b) 6-클로로-2-피리딜, 3-피리딜, 할로겐화 1-메틸-3-피리디늄, 5-브로모-3-피리딜, 5,6-디클로로-3-피리딜, 5-클로로-3-피리딜, 1-옥소-3-피리딜, 4-피리딜, 2-플루오로-4-피리딜, 2-메틸-4-피리딜, 2-메톡시-4-피리딜, 2-시아노-4-피리딜, 1-옥소-4-피리딜, 2-클로로-4-피리틸, 2-클로로-6-메틸-4-피리딜, 2,6-디플루오로-4-피리딜 또는 2,6-디클로로-4-피리딜기; (c) 2-푸릴 또는 3-푸릴기; (d) 2-티에닐, 3-티에닐, 4-클로로-2-티에닐, 5-클로로-2-티에닐, 5-클로로-3-티에닐 또는 2,5-디클로로-3-티에닐기.
  3. 제1항에 있어서, 상기 R3가 알릴, 펜트-2-인일, 프로프-2-인일, 부트-2-인일, 메톡시메틸, 2-메톡시에틸, 아세톤일, 2,2-디메톡시프로필, 펜트-4-엔-2-인일, 3-클로로알릴, 3-요오도프로파길, 3-트리메틸실릴 프로파길 또는 시아노메틸기인 것을 특징으로 하는 화합물.
  4. 제1항에 있어서, 상기 R5가 수소원자, 플루오로, 클로로, 메틸, 에틸 n-프로필, 이소프로필, 프로프-2-인일, 트리멜실릴에틴일, 메틸티오, 메톡시, 메톡시카르보닐메틸, 아릴, 플루오로메틸 또는 트리플루오로메틸기인 것을 특징으로 하는 화합물.
  5. 제1항에 있어서, 상기 R6가 하기 (a)∼(o)중의 어느 하나인 것을 특징으로 하는 화합물 : (a) 메틸, 에틸 n-프로필, n-부틸, n-펜틸, n-헥실, n-헵틸, 이소프로필, 이소부틸, 2차-부틸 또는 3차-부틸기; (b) 2-메틸-1-프로펜일기; (c) 치환되거나 또는 비치환된 페닐기; (d) 3-티에닐, 3-푸릴, 2-티에닐 또는 4-피리딜기; (e) 메톡시 또는 에톡시기; (f0 에톡시카르보닐기; (g0 플루오로, 브로모 또는 클로로기; (h) 트리플루오로메틸, 디플루오로메틸, 펜타플루오로에틸, 트리클로로메틸, 브로모메틸, 클로로메틸 또는 클로로플루오로메틸기; (i) 메틸티오기; (j) 메톡시메틸기; (k) 벤질기; (l) 시클로프로필, 시클로부틸 또는 시클로펜틸기; (m) 디메틸아미노기; (n) 디메틸아미노카르보닐기; (o) 수소원자.
  6. 제1항에 있어서, 상기 X가 산소원자인 것을 특징으로 하는 화합물.
  7. 제1항에 있어서, 상기 X가 산소원자이고, 상기 R2가 치환되거나 또는 비치환된 페닐, 치환되거나 또는 비치환된 피리딜 또는 치환되거나 또는 비치환된 티에닐기이고, R3가 (C3-C6)알킬일기인 것을 특징으로 하는 화합물.
  8. 제7항에 있어서, 상기 R5가 수소원자, 할로 (C1-C4)알킬, 폴리할로(C1-C4)알킬 및(C1-C4)알콕시기에서 선택되고; 상기 R6가 수소원자, 할로, (C1-C4)알킬, 비치환된 페닐, 치환된 페닐, 폴리할로(C1-C4)알킬 및 (C1-C4)알콕시기에서 선택되는 것을 특징으로 하는 화합물.
  9. 제8항에 있어서, 상기 X가 산소원자이고; 상기 R2가 페닐, 3-치환된 페닐 또는 3,5-이치환된 페닐 또는 3,4,5-삼치환된 페닐 또는 2-치환된-4-피리딜 또는 2,6-이치환된-4-피리딜 또는 3-티에닐 또는 5-치환된-3-티에닐기이고; 상기 R3가 (C3-C6)알킬일기이고; 상기 R5수소원자, 할로, (C1-C4)알킬기, 폴리할로(C1-C4)알킬 및(C1-C4)알콕시기에서 선택되고, 상기 R6가 수소원자, 할로, (C1-C4)알킬기, 폴리할로(C1-C4)알킬 및(C1-C4)알콕시기에서 선택되고, 상기 R6가 수소원자, 할로;(C1-C4)알킬, 비치환된페닐, 치환된 페닐, 폴리할로(C1-C4)알킬 및 (C1-C4)알콕시기에서 선택되는 것을 특징으로 하는 화합물.
  10. 제9항에 있어서, 상기 X가 산소원자이고; 상기 R2가 페닐, 3-플루오로페닐, 3-클로로페닐, 3,5-디플루오로페닐, 3,4,5-트리플루오로페닐, 3,5-디클로로페닐, 2-클로로-4-피리딜, 2-플루오로-4-피리딜 또는 2,6-디클로로-4-피리딜, 3-티에닐 또는 5클로로-3-티에닐기이고; 상기 R3가 프로파길기이고; 상기 R5가 수소원자, 메틸, 에틸, 메톡시, 플루오로 또는 클로로이고; 상기 R6가 수소원자, 메틸, 에틸, 이소프로필, n-프로필, n-부틸, 2차-부틸 이소부틸, 3차-부틸, 디플루오로메틸, 트리플루오로메틸, 페닐, 클로로, 브로모 또는 플루오로기인 것을 특징으로 하는 화합물.
  11. 제10항에 있어서, 상기 화합물이 하기 (a)∼(j)중의 어느 하나인 것을 특징으로 하는 화합물: (a) 5,6-디에틸-2-페닐-3-프로파길-4(3H)-피리미딘온; (b) 5-에틸-2-페닐-3-프로파길-6-트리플루오로메틸-4(3H)-피리미딘온; (c)5-에틸-6-이소프로필-2-페닐-3-프로파길-4-(3H)-피리미딘온; (d) 6-클로로-5-에틸-2-페닐-3-프로파길-4(3H)-피리미딘온; (e) 5,6-디에틸-2-(3-플루오로페닐)-3-프로파길-4(3H)-피리미딘온; (f) 2-(2,6-디클로로-4-피리딜)-5,6-디에틸-3-프로파길-4-(3H)-피리미딘온; (g) 5,6-디에틸-2-(3,5-디플루오로페닐)-3-프로파길-4(3H)-피리미딘온; (h) 5-에틸-2-페닐-3-프로파길-6-(n-프로필)-4(3H)-피리미딘온; (i) 6-디플루오로메틸-5-에틸-2-페닐-3-프로파길-4-(3H)-피리미딘온; (j) 6-에틸-5-메톡시-2-페닐-3-프로파길-4(3H)-피리미딘온.
  12. 일반식(Ⅰ)로 표시되는 화합물의 제초적으로 유효한 양을 포함하여 이루어지는 제초성 조성물:
    상기식에서, (a) R˝는 브로모, 클로로, 플루오로, (C1-C12)알킬, 시클로(C3-C8)알킬, (C2-C12)알켄일, 시클로(C3-C8)알켄일, (C2-C12)알킨일, 할로(C1-C12)알킬, 폴라할로(C1-C12)알킬, 할로(C1-C12)알켄일, 폴리할로(C2-C12)알켄일, 할로(C2-C6)알킨일, 폴리할로(C2-C6)알킨일, (C1-C12)알콕시, (C1-C12)알킬티오, (C1-C12)알킬술포닐, (C1-C12)알킬술피닐, 페닐, 펜(C1-C12)알킬, 펜(C2-C12)알켄일, 펜(C2-C12)알킨일, 시아노, 할로(C1-C12)알콕시, 1,3-디옥솔란-2-일, 히드록시이미노; 또는 니트로기에서 독립적으로 선택된 3이하의 치환체로 각기 임의로 치환된 푸릴, 페닐, 나프틸, 피리딜 또는 티에닐기이고; R2가 피리딜일 경우, 이러한 피리딜기는 피리딜기의 질소원자상에 산소원자가 임의로 치환되거나; 또는 R2가 인접탄소원자 또는 푸릴, 페닐, 나프틸, 피리딜 또는 티에닐기에 옥시메틸렌옥시 또는 옥소에틸렌옥시 링크결합을 이루는 접합고리 부분을 갖는 푸릴, 페닐, 나프틸, 피리딜 또는 티에닐기이고; (b) R2는 (C1-C3)알킬, 할로(C1-C3)알킬, 폴리할로(C1-C3)알킬, (C3-C4)알켄일, (C5-C6)알켄인일, (C3-C6)알킨일, (C1-C6)알콕시 (C1-C6)알킬, 디(C1-C6)알콕시(C1-C6)알킬, 할로(C1-C6)알콕시, (C1-C6)알킬, 2-옥소(C2-C3)알킬, 트리메틸실릴(C3-C4)알킨일, 시아노(C1-C6)알킨기, 또는 페닐기이고, 상기 (C1-C3)알킬, (C3-C4)알켄일, (C2-C6)알킨일기 각각은 5이하의 할로겐으로 임의로 치환되며; (c) R5는 수소원자, (C1-C5)알킬, (C3-C6)알켄일, (C2-C6)알킨일, 할로(C1-C6)알킬, 폴리할로(C1-C6)알킬, 할로(C2-C5)알켄일 폴리할로(C2-C6)알켄일, 할로(C2-C6)알킨일, 폴리할로(C2-C6)알킨일, 할로(C1-C6)알콕시, 폴리할로(C1-C6)알콕시, 트리메틸실릴(C2-C3)알킬일, (C1-C6)알콕시, (C1-C6)알킬티오, (C1-C3)알콕시카르보닐(C1-C3)알킬, 할로 또는 시아노기이고; (d) R6는 수소원자, 할로, (C1-C8)알킬, (C2-C6)알켄일, (C2-C6)알킨일, 할로(C1-C6)알킬, 폴리할로(C1-C6)알킬, 할로(C1-C6)알켄일, 폴리할로(C2-C6)알켄일, 할로(C2-C6)알킨일, 폴리할로(C2-C6)알킨일, (C1-C6)알콕시, (C1-C6)알콕시, (C1-C4)알킬, (C1-C6)알킬티오, (C1-C3)알콕시카르보닐, (C1-C3)알콕시카르보닐(C1-C3)알킬, (C6-C10)아릴, 아르(C1-C4)아킬, 시클로(C3-C7)알킬; 푸릴, 피리딜 및 티에닐로 이루어진 군에서 선택된(C4-C5)헤테로시클일, (C1-C3)알킬아미노, 디(C1-C3)알킬아미노, 디(C1-C3)알킬아미노카르보닐, 할로(C1-C8)알킬티오, 폴리할로(C1-C6)알킬티오, 할로(C1-C6)알콕시, 폴리할로(C1-C6)알콕시, (C6-C10)아릴옥시 또는 시아노기이고; 상기 (C6-C10)아릴, 아르(C1-C4)알킬 및 (C6-C10)아릴옥시기는 브르모, 클로로, 플루오로, (C1-C12)알킬, 시클로(C3-C8)알킬, (C2-C12)알켄일, 시클로(C3-C8)알켄일, (C2-C12)알킨일, 할로(C1-C12)알킬, 폴리할로(C1-C12)알킬, 할로(C2-C12)알켄일, 폴리할로 (C2-C12)알켄일, 할로(C2-C6)알킨일, 폴리할로(C2-C6)알킨일, (C1-C12)알콕시, (C1-C12)알킬티오, (C1-C12)알킬술폰일, (C1-C12)알킬술핀일, 페닐, 펜(C1-C12)알킬, 펜(C2-C12)알켄일, 펜(C2-C12)알킨일, 시아노, 할로(C1-C12)알콕시, 1,3-디옥살란-2-일, 히드록시이미노 및 니트로기에서 독립적으로 선택된 3이하의 치환체로 각기 임의로 치환되며; (e) X는 산소원자 또는 황원자이다.
  13. 제12항의 조성물의 제초적으로 유효한 양을 접초자체 또는 잡초 생장지역 또는 잡초의 생장매체에 살포하는 것으로 이루어지는 것을 특징으로 하는 제초방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019930013396A 1992-07-17 1993-07-16 2-아릴피리미딘류 및 이의 제초성 용도 KR940005588A (ko)

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