KR910002798A - 제초 활성을 갖는 시클로헥산디온, 이들을 함유하는 농약 조성물 및 그의 제조방법 - Google Patents

제초 활성을 갖는 시클로헥산디온, 이들을 함유하는 농약 조성물 및 그의 제조방법 Download PDF

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KR910002798A
KR910002798A KR1019890010502A KR890010502A KR910002798A KR 910002798 A KR910002798 A KR 910002798A KR 1019890010502 A KR1019890010502 A KR 1019890010502A KR 890010502 A KR890010502 A KR 890010502A KR 910002798 A KR910002798 A KR 910002798A
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alkyl
hydrogen
cyclohexanedione
alkoxy
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게오르그 부르너 한스
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베르너 발데크
시바-가이기 아게
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Abstract

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Description

제초 활성을 갖는 시클로헥산디온, 이들을 함유하는 농성 조성물 및 그의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (34)

  1. 하기 일반식(Ⅰ) 또는 (Ⅰ')의 시클로헥산-1,3-디온 :
    상기식에서, R 및 R2는 서로 독립해서 수소 ; 할로겐; 니트로; 시아노; C1-C4알킬; C1-C4알콕시; C1-C4알킬-S(O)n-;COR8; C1-C4할로알콕시; 또는 C1-C4할로알킬이고; R3, R4및 R5는 서로 독립해서 수소; C1-C4알킬; 또는 비치환되거나 또는 할로겐, 니트로, C1-C4알킬, C1-C4알콕시, C1-C4알킬-S(O)n-, C1-C4할로알킬, C1-C4할로알킬-S(O)n- 및 C1-C4할로알콕시로부터 선정된 동일하거나 상이한 3이하의 치환체로 치환된 페닐 또는 벤질이며 ; R6은 수소; C1-C4알킬; C1-C4알콕시카르보닐; 또는 시아노이고 ; R7은 OH ; 또는 O M이며 ; R8은 OH; C1-C4알콕시; HN2; C1-C4알킬아미노; 또는 디-C1-C4알킬아미노이고; n은 0, 1 또는 2이며 ; M은 금속이온의 양이온 또는 비치환되거나 또는 3이하의 C1-C4알킬, C1-C4히드록시알킬 또는 C1-C4알콕시-C1-C4알킬기로 치환된 암모늄 이온의 양이온임.
  2. 제1항에 있어서, 하기 일반식(Ⅰ) 또는 (Ⅰ')의 시클로헥산디온 :
  3. 제1항에 있어서, 하기 일반식(Ⅰ) 또는 (Ⅰ')의 시클로헥산디온 :
  4. 제2항 또는 제3항에 있어서, 하기 일반식(Ⅰ) 또는 (Ⅰ')의 시클로헥산디온:
    상기식에서, 라디칼 R1및 R2가 피리딘 고리의 3- 및 5-위치에서 결합되고 또 피리딘 카르보닐계는 피리딘 고리의 2-위치를 통하여 결합됨.
  5. 제1항에 있어서, 하기 일반식(Ⅰ) 또는 (Ⅰ')의 시클로헥산디온 :
    상기식에서, R1은 수소 ; 할로겐 ; 니트로 ; 시아노 ; C1-C4알킬 ; C1-C4알콕시 ; C1-C4알킬-S(O)n- ; COR8; C1-C4할로알콕시 ; 또는 C1-C4할로알킬이고 ; R2는 수소 ; 할로겐 ; 니트로 ; 시아노 ; C1-C4알킬 ; C1-C4알콕시 ; C1-C4할로알콕시 ; C1-C4알킬-S(O)n- ; 또는 C1-C4할로알킬이고 ; R3, R4및 R5는 서로 독립해서 수소 ; C1-C4알킬 ; 또는 비치환되거나 또는 할로겐, 니트로, 시아노, C1-C4알킬, C1-C4알콕시, C1-C4알킬-S(O)n- , C1-C4할로알킬, C1-C|4할로알킬--S(O)n- 및 C1-C4할로알콕시로부터 선정된 동일하거나 상이한 3이하의 치환체에 의해 치환된 페닐 또는 벤질이고 ; R6은 수소 C1-C4알콕시카르보닐 ; 또는 시아노이며 ; R7은 OH ; 또는 OM이며 ; R8은 OH ;C1-C4알콕시 ; HN2;C1-C4알킬아미노 ; 또는 디-C1-C4알킬아미노이고 ; n은 0, 1 또는 2이며 ; M은 알칼리 금속 이온, 알칼리 토금속 이온 또는 암모늄 이온의 양이온 ; 모노 -C1-C4알킬암모늄 이온의 양이온 ; 디-C1-C4알킬암모늄 이온의 양이온 ; 트리-C1-C4알킬암모늄 이온의 양이온 ; 또는 트리에탄올암모늄 이온의 양이온임.
  6. 제1항 내지 제5항중 어느 하나에 있어서, 라디칼 R3내지 R6의 적어도 하나가 수소인 일반식(Ⅰ) 또는 (Ⅰ')의 시클로헥산디온.
  7. 제1항 내지 제5항중 어느하나에 있어서, 라디칼 R3내지 R6의 적어도 2개가 수소인 일반식(Ⅰ) 또는 (Ⅰ')의 시클로헥산디온.
  8. 제1항 내지 제5항중 어느 하나에 있어서, R6이 시아노이고 또 R5가 수소인 일반식(Ⅰ) 또는 (Ⅰ')의 시클로헥산디온.
  9. 제1항 내지 제5항중 어느 하나에 있어서, R6이 시아노이고 또 R5가 수소이며 또 R3및 R4가 독립적으로 수소 또는 C1-C4알킬인 일반식(Ⅰ) 또는 (Ⅰ')의 시클로헥산디온.
  10. 제1항 내지 제5항중 어느 하나에 있어서, R6이 C1-C4알콕시카르보닐인 일반식(Ⅰ) 또는 (Ⅰ')의 시클로헥산디온.
  11. 제1항 내지 제5항중 어느 하나에 있어서, R7이 OH인 일반식(Ⅰ) 또는 (Ⅰ')의 시클로헥산디온.
  12. 제1항 내지 제5항중 어느 하나에 있어서, R7이 O-M인 일반식(Ⅰ) 또는 (Ⅰ')의 시클로헥산디온.
  13. 제1항 내지 제5항중 어느 하나에 있어서, R1이 수소, 염소, 불소, 니트로, 트리풀루오로메틸, 메톡시, 브롬, 메틸티오, 메틸술포닐, 카르복시, 트리클로로메틸 또는 메틸인 일반식(Ⅰ) 또는 (Ⅰ')의 시클로헥산디온.
  14. 제1항 내지 제5항중 어느 하나에 있어서, R2`가 수소, 염소, 니트로, 메틸티오, 메틸술피닐, 메틸술포닐, 메틸, 불소, 트리풀루오로메틸 또는 트리클로로메틸인 일반식(Ⅰ) 또는 (Ⅰ')의 시클로헥산디온.
  15. 제1항 내지 제5항중 어느 하나에 있어서, R1이 수소; 염소; 브롬; 니트로, 시아노; 메틸; 트리풀루오로메틸; 트리클로로메틸; 메톡시; 메틸티오; 메틸술피닐; 메틸술포닐; 카르복시; 카르바모일; 메톡시카르보닐 또는 에톡시카르보닐이고; R2가 수소; 불소; 염소; 니트로; 트리풀루오로메틸; 트리클로로메틸; 메틸티오; 메틸술피닐; 또는 메틸술포닐이며; R3이 수소; C1-C3알킬; 페닐; 벤질; 또는 클로로페닐이고, R5는 수소; 또는 메틸이며, R6는 수소; 또는 메틸이고; R6는 수소; 시아노; 메틸; 또는 C1-C2알콕시카르보닐; R7은 OH; 또는 O-M이고; M_는 나트륨, 리튬, 칼슘, 트리메틸암모늄 또는 트리에탄올암노늄 이온 양이온의 일반식(Ⅰ) 또는 (Ⅰ')의 시클로헥산디온.
  16. 제1항에 있어서, 일반식(Ⅰ)의 화합물이 2-(3-클로로-5-트리풀루오로메틸피리딘-2-알카르보닐)-시클로헥스-1-엔-1-올-3-온 또는 2-(3-클로로-5-메틸술포닐피리딘-2-일카르보닐)-시클로헥스-1-엔-1-올-3-온인 화합물.
  17. a)염기 존재하에서, 하기 일반식(Ⅱ)의 시클로헥산디온을 하기 일반식(Ⅲ)의 피리딘과 반응시키거나, 또는 b)하기 일반식(Ⅳ) 또는 (Ⅳ')의 에스테르를 열에의한 자리옮김 반응시키는 것을 포함하는 하기 일반식(Ⅰa) 또는 (Ⅰa')의 시클로헥산디온의 제조방법.
    상기식에서, 라디칼 R1내지 R6은 상기 정의한 바와같고, R7은 OH이며, X는 할로겐, 바람직하게는 염소 또는 브롬이거나 또는 라디칼또는이고, 또 R8은 C1-C4알킬, 페닐 또는 벤질임.
  18. 하기 일반식(Ⅰa) 또는 (Ⅰa')의 시클로헥산디온을 하기 일반식(Ⅴ)의 염기와 반응시키는 것을 포함하는 하기 일반식(Ⅰb) 또는 (Ⅰb')의 시클로헥산디온의 염의 제조방법.
    상기식에서, 라디칼 R1내지 R6및 M은 제1항 내지 제10항 또는 제12항 내지 제15항중 어느 하나에서 정의된 바와같고, B는이며, R7은 일반식(Ⅰa) 또는 (Ⅰa')에서는 OH이고, 일반식(Ⅰ) 또는 (Ⅰ')에서는이다.
  19. 하기 일반식(Ⅰd) 또는 (Ⅰd')의 티오에테르를 산화시키는 것을 포함하는, 제1항에 따른 일반식(Ⅰc) 또는 (Ⅰc')의 화합물의 제조방법.
    상기식(Ⅰd) 또는 (Ⅰd')에서, 산화될 라디칼 R1내지 R6이 C1-C4알킬-S(O)|n-이고, n 은 0이며, 나머지 라디칼은 상기 정의한 바와같으며, 일반식(Ⅰc) 또는 (Ⅰc)중에서, 라디칼 R1내지 R6의 1개 이상은 C1-C4알킬-S(O)|n-이고, n은 1 또는 2이며 또 나머지 라디칼은 상기 정의한 바와같다.
  20. 하기 일반식(Ⅹ)의 할로피리딘을 Pd촉매 존재하에서 일산화탄소 및 알코올 R'OH과 반응시키는 것을 포함하는, 하기 일반식 (ⅩⅠ)의 피리딘-2-카르복시산 에스테르의 제조방법 :
    상기식에서, R1및 R2제1항, 제3항, 제4항, 제5항, 제13항, 제14항, 제15항 또는 제16항중의 어느 하나에서 정의된 바와같고, R'은 C1-C4알킬이며 또 Hal은 할로겐임.
  21. 하기 일반식(Ⅳ) 또는 (Ⅳ')의 화합물 :
    상기식에서 라디칼 R1내지 R6은 제1항 내지 제10항 또는 제13항 내지 제16항중 어느 하나에서 정의된 바와 같다.
  22. 하기 일반식(ⅩⅤ)의 피콜린산 유도체 :
    상기식에서, Y는 OH; C1-C4알콕시; 또는 할로겐이고; R1및 R2는 서로 독립해서 할로겐; 니트로; 시아노; C1-C4할로알킬; C1-C4알킬; C1-C4알콕시; 또는 C1-C4알킬-S(O)n-이며; 또 n은 0;1; 또는 2이고; 단 Y가 염소이고 라디칼 R1이 3위치에 결합되어 있고 또 라디칼 R2가 5위치에 결합될때, R1및 R2는 동시에 염소가 아니거나 또는 동시에 메틸이고, 또는 R1이 니트로일 때 R2는 메틸이 아니다.
  23. 제22항에 있어서, 하기 일반식(ⅩⅤ')의 피콜린산 유도체 :
    상기식에서, Y는 OH; C1-C4알콕시; 또는 할로겐이고; R1및 R2는 서로 독립해서 할로겐; 니트로; 시아노; C1-C4할로알킬; C1-C4알킬; C1-C4알콕시; 또는 C1-C4알킬-S(O)n-이며; 또 n은 0;1; 또는 2이고; 단 Y가 염소이면, R1및 R2가 동시에 염소가 아니거나 또는 동시에 메틸이고, 또는 R1이 니트로이고 R2는 메틸임.
  24. 제23항에 있어서, Y가 OH; C1-C4알콕시; 또는 할로겐이고; R1이 수소이며; 또 R2가 C1-C4알콕시; C1-C4할로알킬; 또는 시아노인 일반식(ⅩⅤ')의 피콜린산 유도체.
  25. 제23항에 있어서, Y가 OH; C1-C4알콕시; 또는 할로겐이고; R1이 C1-C4알콕시; C1-C4할로알킬; 또는 시아노이며; 또 R2는 수소인 일반식(ⅩⅤ')의 피콜린산 유도체.
  26. 제22항 내지 제25항중 어느하나에 있어어, Y가 염소인 피콜린산 클로라이드.
  27. 하기 일반식(Ⅱ)의 시클로헥산디온을 하기 일반식(Ⅲ)의 피리딘으로 0-아실화하는 것에 의하여 제21항에 따른 일반식(Ⅳ) 또는 (Ⅳ')의 화합물을 제조하는 방법 :
    상기식에서, R1내지 R6은 상기 정의된 바와같고, X는 할로겐, 바람직하게는 염소 또는 브롬, 또는 라디칼또는이고, 또 R8은 C1-C4알킬, 페닐 또는 벤질임.
  28. 보조제 및/또는 담체와 함께 제1항 내지 제16항중 어느 하나에 따른 일반식(Ⅰ)의 화합물을 함유하는 제초제 조성물.
  29. 일반식(Ⅰ)의 화합물을 보조제 및/또는 담체와 함께 혼합하는 것을 포함하는 제28항에 따른 제초제 조성물의 제조방법.
  30. 바람직하지 않는 식물 생장을 방제하기 위한 제1항 내지 제16항중 어느 하나에 따른 일반식(Ⅰ)의 화합물의 용도.
  31. 제1항 내지 제16항에 따른 일반식(Ⅰ)의 화합물 또는 제28항중 따른 조성물을 방제될 식물 또는 이들의 소재지에 투여하는 것을 포함하는 바람직하지 않은 식물 생장의 억제방법.
  32. 제31항에 있어서, 유용작물에서 잡초 또는 풀을 방제하는 방법.
  33. 제31항에 있어서, 곡류, 목화, 간장콩, 옥수수, 벼, 사탕수수 또는 소금(sorghum)에서 잡초 또는 풀을 출아전 또는 출아후에 방제하는 방법.
  34. 제1항 내지 제16항중 어느 하나에 따른 일반식(Ⅰ)의 화합물을 제초 유효량만큼 함유하는 종자.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019890010502A 1988-07-25 1989-07-25 제초 활성을 갖는 시클로헥산디온, 이들을 함유하는 농약 조성물 및 그의 제조방법 KR910002798A (ko)

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