KR950701318A - 닌드기살충용, 곤충살충용 및 선충살충용 치환된 (헤테로) 아릴알킬 케톤 옥심0 -에테르, 그의 제조 방법, 이를 함유한 살충제 및 살충제로서의 용도(acaricidal, insecticidal and nematicidal substituted (hetero) arylalkyl ketone oxime 0-ethers, processes for preparing the same, agent containing the same and its use as pest control agent) - Google Patents

닌드기살충용, 곤충살충용 및 선충살충용 치환된 (헤테로) 아릴알킬 케톤 옥심0 -에테르, 그의 제조 방법, 이를 함유한 살충제 및 살충제로서의 용도(acaricidal, insecticidal and nematicidal substituted (hetero) arylalkyl ketone oxime 0-ethers, processes for preparing the same, agent containing the same and its use as pest control agent)

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Publication number
KR950701318A
KR950701318A KR1019940703734A KR19940703734A KR950701318A KR 950701318 A KR950701318 A KR 950701318A KR 1019940703734 A KR1019940703734 A KR 1019940703734A KR 19940703734 A KR19940703734 A KR 19940703734A KR 950701318 A KR950701318 A KR 950701318A
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South Korea
Prior art keywords
alkyl
optionally substituted
aryl
heteroaryl
substituted
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KR1019940703734A
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English (en)
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KR0173146B1 (ko
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쿤 비르기트
될레르 우베
쉬나테레르 스테판
슈베르트 한스-헤르베르트
크나우프 베르너
발테르스도르퍼 안나
케른 만프레트
Original Assignee
울리히 테르가우, 위르겐 루츠
훽스트 쉐링 아그레보 게엠베하
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Publication of KR950701318A publication Critical patent/KR950701318A/ko
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Publication of KR0173146B1 publication Critical patent/KR0173146B1/ko

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Abstract

본 발명은 하기 일반식(Ⅰ)의 화합물에 관한 것이다 :
상기 식에서, Ar1및 Ar2는 치환될 수 있는 아릴 또는 헤테로아릴이고, R은 가능한 치환된 지방족 또는 치환족 잔기이다.
또한, 본 발명은 상기 화합물의 제조 방법, 이를 함유하는 약제 및 동물의 해충을 방제하는 그의 용도를 개시하고 있다.

Description

닌드기살충용, 곤충살충용 및 선충살충용 치환된 (헤테로) 아릴알킬 케톤 옥심 0-에테르, 그의 제조 방법, 이를 함유한 살충제 및 살충제로서의 용도(ACARICIDAL, INSECTICIDAL AND NEMATICIDAL SUBSTITUTED (HETERO) ARYLALKYL KETONE OXIME O-ETHERS, PROCESSES FOR PREPARING THE SAME, AGENT CONTAINING THE SAME AND ITS USE AS PEST CONTROL AGENT)
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (16)

  1. syn 또는 anti 화합물 또는 이들의 혼합 형태의 일반식(Ⅰ)의 화합물 또는 그의 염 :
    상기식에서, Ⅰ. Ar1및 Ar2는 동일하거나 또는 상이하며, a) 10개 이하의 탄소 원자를 가진 (C6-C12)-아릴 또는 헤테로아릴 또는 b) Ⅰ. a)에 정의된 바와 같으며, 하기 1-45를 포함하는 그룹중에서 선택된 동일하거나 또는 상이한 5개 이하의 치환체를 갖고; 1. (C1-C6)-알킬, 2. (C2-C6)-알케닐, 3. (C2-C6)-알키닐, 4. 할로겐 및 (C1-C4)-알킬을 포함하는 그룹중에서 선택된 동일하거나 또는 상이한 6개 이하의 라디칼로 임의로 치환된 (C3-C8)-사이클로알킬, 5. 할로겐, 6. (C1-C6)-할로알킬, 7. (C2-C6)-할로알케닐, 8. (C2-C6)-할로알키닐, 9. (C1-C6)-알콕시-(C1-C6)-알킬, 10. (C1-C6)-알킬, (C1-C6)-알콕시, (C1-C6)-할로알킬 및 (C1-C6)-할로알콕시를 포함하는 그룹중에서 선택된 동일하거나 또는 상이한 3개 이하의 라디칼로 임의로 치환된 (C6-C12)-아릴, 11. 10개 이하의 탄소 원자를 가지며, Ⅰ. b)10에 기재된 바와 같이 임의로 치환된 헤테로아릴, 12. Ⅰ. b)10. 기재된 바와 같이 아릴 잔기에서 임의로 치환된 (C6-C12)-아릴-(C1-C4)-알킬, 13. 헤테로아릴 잔기에 10개 이하의 탄소 원자를 가지며 Ⅰ. b)10. 에 기재된 바와 같이 헤테로아릴 잔기에서 임의로 치환된 헤테로아릴-(C1-C4)-알킬, 14. (C1-C6)-알콕시, 15. (C2-C6)-알케닐옥시, 16. (C2-C6)-알키닐옥시, 17. Ⅰ. b)4. 에 기재된 바와 같이 임의로 치환된 (C3-C8)-사이클로알킬옥시, 18. (C1-C6)-알콕시-(C1-C4)-알콕시, 19. Ⅰ. b)10. 에 기재된 바와 같이 임의로 치환된 (C6-C12) 아릴옥시, 20. 10개 이하의 탄소 원자를 가지며 Ⅰ. b)10. 에 기재된 바와 같이 임의로 치환된 헤테로아릴옥시, 21. (C1-C6)-할로알콕시, 22. (C2-C6)-할로알케닐옥시, 23. (C2-C6)-할로알키닐옥시, 24. -O-N=CR′2(여기서, 라디칼 R′는 할로겐, (C1-C6)-알킬, (C3-C6)-사이클로알킬 및 (C6-C12)-아릴을 포함하는 그룹 중에서 선택된 동일하거나 또는 상이한 라디칼이다), 25. (C1-C6)-알킬아미노, 26. 디-(C1-C6)-알킬아미노, 27. Ⅰ.b)4. 에 기재된 바와 같이 임의로 치환된 (C3-C8)-사이클로알킬아미노, 28. Ⅰ.b)10. 에 기재된 바와 같이 임의로 치환된 (C6-C12)-아릴아미노, 29. 10개 이하의 탄소 원자를 가지며 Ⅰ. b)10. 에 기재된 바와 같이 임의로 치환된 헤테로아릴아미노, 30. (C1-C6)-알킬머캅토, 31. (C6-C12)-아릴머캅토, 32. 10개 이하의 탄소 원자를 가진 헤테로아릴머캅토, 33. (C1-C6)-알킬설피닐, 34. (C6-C12)-아릴설피닐, 35. 10개 이하의 탄소 원자를 가진 헤테로아릴설피닐, 36. (C1-C6)-알킬설포닐, 37. (C6-C12)-아릴설포닐, 38. 10개 이하의 탄소 원자를 가진 헤테로아릴설포닐, 39. 니트로, 40. 시아노, 41. 시아노-(C1-C6)-알킬, 42. (C1-C6)-알콕시카보닐, 43. (C6-C12)-아릴옥시카보닐 및 44. 헤테로아릴 잔기에 10개 이하의 탄소 원자를 가진 헤테로아릴옥시카보닐 또는 45. a) 치환체들중 2개가 메틸렌디옥시이고, b) 상기 메틸렌디옥시 그룹이 할로겐 및 (C1-C4)-알킬을 포함하는 그룹중에서 선택된 동일하거나 또는 상이한 하나 또는 2개의 라디칼로 임의로 치환되며; Ⅱ. R은 a) (C1-C6)-알킬, b) (C2-C6)-알케닐, c) (C2-C6)-알키닐 또는 d) (C3-C8)-사이클로알킬, 또는 e) Ⅱ. a)-d)에 정의된 바와 같으며, 하기 치환체를 포함하는 그룹중에서 선택된 동일하거나 또는 상이한 3개 이하의 치환체를 가지며; 1. 할로겐, 2. 하이드록실, 3. (C1-C6)-알콕시, 4. (C1-C6)-알킬머캅토, 5. (C1-C6)-알킬설피닐, 6. (C1-C6)-알킬설포닐, 7. 사이노, 8. 니트로 및 9. (C1-C6)-알콕시카보닐 또는 f) Ⅱ. a)-d)에 정의된 바와 같으며 수소 원자 수가 5이상이면, 이러한 수소 원자 모두는 할로겐으로 치환되어 할로겐 원자 수가 4이상이고; 또한 Ⅰ. a) 및 b)에 정의된 바와 같이 아릴 및 헤테로아릴이 부분적으로 수소화 분해될 수 있고, 이러한 아릴 및 헤테로아릴, 잔기의 CH2그룹 하나 또는 2개가 CO로 치환될 수 있고; Ⅲ. 단, a) R이 메틸 또는 Ⅱ. e) 1. 또는 3. -9.에 정의된 바와 같이 동일하거나 또는 상이한 1 내지 3개의 라디칼을 갖는 치환된 메틸인 경우, 이들중 적어도 하나의 라디칼이 할로겐이며, Ar1이 Ⅱ. b) 2. -4., 7., 8., 11., 13., 15. -44. 또는 45. b)에 기재된 바와 같이 치환된 아릴, 또는 임의로 치환된 헤테로아릴인 경우, Ar2는 Ⅱ. a) 또는 b)에 기재된 바와 같고, b) R이 메틸 또는 Ⅱ. e)1. 또는 3. -9. 에 정의된 바와 같이 동일하거나 또는 상이한 1 내지 3개의 라디칼을 갖는 치환된 메틸인 경우, 이들중 적어도 하나의 라디칼이 할로겐이며, Ar1이 Ⅰ. b) 1., 5., 6., 9., 10., 12., 14. 또는 45a)에 기재된 바와 같이 치환된 아릴인 경우, Ar2는 Ⅰ.a) 또는 b)에 기재된 바와 같으나, 4-플루오로-3-페녹시페닐, 3-페녹시페닐, 펜타플루오로페닐 또는 2, 6-디할로페닐이 아니며, c) R이 (C2-C6)-알킬 또는 Ⅱ. b)-f)에 정의된 바와 같고, Ar1는 Ⅰ. a)에 정의된 바와 같거나 또는 Ⅰ. b)에 정의된 바와 같이 아릴 또는 Ⅰ. b)1. -20. 또는 24. -45. 에 정의된 바와 같이 헤테로아릴인 경우, Ar2는 Ⅰ. a) 및 b)에 기재된 바와 같으나, 하기 화합물은 아니고,
    2,6-디할로페닐, 펜타플루오로페닐,
    (여기서, Z는 할로겐 또는 수소이고, Q는 O, S, NH 또는 CH2이며, R4는 할로겐이고, X는 O 또는 S이며, R10, R11및 R12는 동일하거나 또는 상이하며, 수소 또는 Ⅰ. b)1. -45.에 정의된 바와 같고, R13은 수소, 불소 또는 메틸이고, o는 0, 1 또는 2이며, R6은 수소, 불소 또는 알킬이고, R7은 할로페녹시, 할로벤질, -O-CH2-CH=CH2, -O-CH2-C≡CH, CH2-CH=CH2, 또는 CH2-C≡CH이며, R8은 알케닐 또는 할로알케닐이다), d) R이 (C2-C6)-알킬 또는 Ⅱ. b)-f)에 정의된 바와 같고, Ar1이 Ⅰ. b)21. -23.에 정의된 바와 같은 헤테로아릴인 경우, Ar2는 부가적으로 Ⅰ. a) 및 b)에 정의된 바와 같을 수 있고, e) R이 (C2-C6)-알킬 또는 Ⅱ. b)-f)에 정의된 바와 같고, Ar1이 Ⅰ. a) 또는 b)에 정의된 바와 같은 헤테로아릴인 경우, Ar2는 부가적으로 펜타플루오로페닐 또는
    (여기서, R13및 o는 상기 정의한 바와 같다)이며, f) R이 Ⅱ. e)에 정의된 바와 같이 치환된 (C2-C6)-알킬, (C2-C6)-알케닐 또는 (C2-C6)-알키닐이고, Ar1이 Ⅰ. a) 또는 b)에 정의된 바와 같이 아릴인 경우, Ar2는 부가적으로
    (여기서, R13및 o는 상기 정의한 바와 같다)이고, 및 g) R이 (C2-C6)-알킬 또는 Ⅱ. b)-f)에 정의된 바와 같고, Ar1이 Ⅰ. b)21. 에 정의된 바와 같은 치환된 (C6-C12)-아릴인 경우, Ar2는 부가적으로 펜타플루오로페닐이다.
  2. 제1항에 있어서, Ar1이 각각 제1항에 정의된 바와 같이 임의로 치환된 페닐 나프틸, 인다닐, 벤조푸릴, 벤조티에닐,
    (여기서, X는 O, S 또는 NR3이며, R3은 수소; (C1-C6)-알킬; (C2-C6)-알케닐; (C2-C6)-알키닐; 할로겐 및 (C1-C4)-알킬을 포함하는 그룹중에서 선택된 동일하거나 또는 상이한 6개 이하의 라디칼로 임의로 치환된 (C3-C8)-사이클로알킬; (C1-C6)-할로알킬; (C2-C6)-할로알케닐; (C2-C6)-할로알키닐; (C1-C6)-알콕시(C1-C6)-알킬; (C6-C12)-아릴-(C1-C4)-알킬; 헤테로아릴 잔기에 10개 이하의 탄소 원자를 가진 헤테로아릴-(C1-C4)-알킬; 시아노-(C1-C6)-알킬; (C1-C6)-알콕시카보닐 (C6-C12)-아릴옥시카보닐; 또는 10개 이하의 탄소 원자를 가진 헤테로아릴옥시카보닐이다)인 화합물 또는 그의 염.
  3. 제1 또는 2항에 있어서, Ar1이 하기 일반식의 라디칼
    (여기서, X는 제2항에 정의한 바와 같으며, P는 0 내지 5의 정수이고, 라디칼 R1이 동일하거나 상이하며, 할로겐; (C1-C6)-알킬; (C2-C6)-알케닐; (C2-C6)-알키닐; 할로겐 및 (C1-C4)-알킬을 포함하는 그룹중에서 선택된 동일하거나 또는 상이한 6개 이하의 라디칼로 임의로 치환된 (C3-C8)-사이클로알킬; (C1-C6)-할로알킬; (C2-C6)-할로알케닐; (C2-C6)-할로알키닐; (C1-C6)-할로알킬 및 (C1-C6)-할로알시로 이루어진 그룹중에서 선택된 동일하거나 또는 상이한 3개 이하의 라디칼로 임의로 치환된 (C6-C12)-아릴; 10개 이하의 탄소 원자를 가지며 전술한 아릴과 같이 임의로 치환된 헤테로아릴; 전술한 아릴과 같이 아릴 잔기에 임의로 치환된 (C6-C12)-아릴-(C1-C4)-알킬; 헤테로아릴잔기에 10개 이하의 탄소 원자를 가지며 전술한 아릴과 같이 상기 잔기에 임의로 치환된 헤테로아릴-(C1-C4)-알킬; (C1-C6)-알콕시; (C2-C6)-알케닐옥시; (C2-C6)-알키닐옥시; (C3-C8)-사이클로알킬옥시; (C1-C6)-알콕시-(C1-C6)-알콕시; 전술한 아릴과 같이 임의로 치환된 (C6-C12)-아릴옥시; 10개 이하의 탄소 원자를 가지며 전술한 아릴과 같이 임의로 치환된 헤테로아릴옥시; (C1-C6)-할로알콕시, (C2-C6)-할로알케닐옥시, (C2-C6)-할로알키닐옥시 또는 -O-N=CR′2(여기서, R′는 수소, (C1-C6)-알킬, (C3-C8)-사이클로알킬 및 (C8-C12)-아릴을 포함하는 그룹중에서 선택된 동일하거나 또는 상이한 라디칼이다); 또는 R1에 대한 라디칼중 2개가 Ⅰ. b)45. b)에 기재된 바와 같이 임의로 치환된 메틸렌디옥시이다)인 화합물 또는 그의 염.
  4. 제3항에 있어서, R1이 (C1-C6)-알킬; (C2-C6)-알케닐; (C3-C8)-사이클로알킬; 할로겐; (C1-C6)-할로알킬; (C2-C6)-할로알케닐; (C2-C6)-할로알키닐; 10개 이하의 탄소 원자를 가진 헤테로아릴 또는 제3항에 기재된 바와 같이 임의로 치환된 (C6-C12)-아릴; (C1-C6)-알콕시; (C2-C6)-알케닐옥시; (C2-C6)-알키닐옥시; (C3-C8)-사이클로알킬옥시; 10개 이하의 탄소 원자를 가진 헤테로아릴옥시 또는 제3항에 기재된 바와 같이 임의로 치환된 (C6-C12)-아릴옥시; (C1-C6)-알콕시-(C1-C6)-알킬; (C1-C6)-알콕시-(C1-C6)-알콕시; (C1-C6)-할로알콕시; (C2-C6)-할로알케닐옥시; 또는 (C2-C6)-할로알키닐옥시; 또는 라디칼 R1중 2개가 Ⅰ. b)45. b)에 기재된 바와 같이 임의로 치환된 메틸렌디옥시인 화합물 또는 그의 염.
  5. 제3 또는 4항에 있어서, R1이 (C1-C6)-할로알콕시, 예를 들면 OCHF2, OCF3, OCF2CF2H, OCH2CF3또는 OCH(CF3)2, (C1-C6)-알콕시, 불소, 염소, 브롬, (C1-C6)-알킬, (C2-C6)-할로알케닐옥시, (C2-C6)-할로알키닐옥시, (C1-C6)-할로알킬, (C2-C6)-할로알케닐 또는 (C2-C6)-할로알키닐인 화합물 또는 그의 염.
  6. 제3 내지 제5항중 어느 한항에 있어서, Ar1[lacuna]이
    (여기서, R1`및 X는 제2내지 5항중 어느 한항에 정의된 바와 같다)인 화합물 또는 그의 염.
  7. 제1 내지 6중 어느 한항에 있어서, R이 각각 할로겐으로 부분적으로 또는 전체적으로 치환될 수 있는 (C1-C6)-알킬 또는 (C3-C8)-사이클로알킬, 바람직하게는 3개 이하의 불소 원자로 치환될 수 있는 (C1-C6)-알킬인 화합물 또는 그의 염.
  8. 제2 내지 제7항중 어느 한항에 있어서, Ar2는 특히
    (여기서 A, B 및 C는 동일하거나 상이하며, N, CH 또는 C-Hal이고, Q는 O, S, NH 또는 CH2, 바람직하게는 O 또는 CH2이며, R4는 수소, 할로겐, O-CH2-CH=CH=CH2또는 O-CH2-C≡CH, 바람직하게는 4-F, 3-F, 4-Cl이고, Hal은 할로겐이며, R9는 수소 또는 R1에 대한 정의와 같고, m 및 n은 동일하거나 또는 상이하며, 각각의 경우에 1, 2, 3 또는 4이며, m+n은 5이고, R5는 수소 또는 제3항에서의 R1에 대한 정의와 같고, q, r 및 s는 동일하거나 또는 상이하며, 각각의 경우에 1, 2 또는 3이고, q+r+s는 5이며, R3은 상기 정의한 바와 같으며, R10, R11및 R12는 상기 정의한 바와 같고, 바람직하게는 CH3, CF3, CN, 페닐, -CH2-CH=CH2, -CH2-C≡CH 또는 벤질이고, R13는 수소, 불소 또는 메틸이며, o는 0, 1 또는 2이고, R6은 수소, 불소 또는 (C1-C6)-알킬이며, R7은 할로페녹시, 할로벤질, O-CH2-CH=CH2, O-CH2-C≡CH, -CH2-CH=CH2또는 -CH-C≡CH2이고, 및 R8는 (C1-C6)-알케닐 또는 (C2-C6)-할로알케닐이다)인 화합물 또는 그의 염.
  9. 제1 내지 8항중 어느 한항에 있어서, Ar1이 임의로 치환된 헤테로아릴이고, R이 트리플루오로메틸인 화합물 또는 그의 염.
  10. 제1 내지 9항중 어느 한항에 있어서, Ar2가 제8항의 B.c), B.d), C.b), C.c) 또는 C.d)에 정의한 바와 같은 화합물 또는 그의 염.
  11. 제1 내지 제10항중 어느 한항에 있어서, Ar1이 임의로 치환된 아릴 또는 헤테로아릴이고, Ar2가 제8항의 D. 또는 E. 에 정의한 바와 같고, R이 트리플루오로메틸인 화합물 또는 그의 염.
  12. a) M이 수소인 경우, 적합한 염기의 존재하에 일반식(Ⅱ)의 화합물을 일반식(Ⅲ)의 화합물과 반응시키는 단계; 또는 b) 경우에 따라 적합한 염기의 존재하에, 일반식(Ⅳ)의 화합물을 일반식(Ⅴ)의 화합물 또는 그의 염과 반응시키고, 경우에 따라, 일반식(Ⅰ)의 생성 화합물을 그의 염으로 전환시키는 단계를 포함하는 제1 내지 제11항중 어느 한항에 청구된 화합물의 제조 방법 :
    상기 식에서, Ar1, Ar2및 R은 일반식(Ⅰ)의 정의에서와 동일하며, M은 수소 또는 알칼리 금속 원자이고, X은 이탈기이다.
  13. 제1 내지 제11항중 어느 한항에 청구된 적어도 하나의 화합물을 통상적인 첨가제 또는 보조제와 함께 포함하는 곤충살충제, 진드기살충제 또는 선충살충제.
  14. 제1 내지 제11항중 어느 한항에 청구된 화합물 효과량을 해충, 진드기 및 선충류 또는 이에 감염된 농작물, 지역 또는 기질에 적용하는, 해충, 진드기 및 선충류의 방제 방법.
  15. 해충, 진드기 및 선충류를 방제하기 위한 제1 내지 제11항중 어느 한항에 청구된 화합물의 용도.
  16. 장내기생충 또는 외부기생충 및 선충류를 방제하기 위한 제1 내지 제11항중 어느 한항에 청구된 화합물의 용도.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019940703734A 1992-04-22 1993-04-16 진드기살충용,곤충살충용 및 선충살충용 치환된 (헤테로아릴알킬 케톤 옥심 o-에테르, 그의 제조 방법, 이를 함유한 살충제 및 살충제로서의 용도 KR0173146B1 (ko)

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DE4213149A DE4213149A1 (de) 1992-04-22 1992-04-22 Akarizide, insektizide und nematizide substituierte (Hetero)-Aryl-Alkyl-ketonoxim-O-ether, Verfahren zu ihrer Herstellung, sie enthaltende Mittel und ihre Verwendung als Schädlingsbekämpfungsmittel
DEP4213149.9 1992-04-22
PCT/EP1993/000916 WO1993021157A2 (de) 1992-04-22 1993-04-16 Akarizide, insektizide und nematizide substituierte (hetero)-aryl-alkyl-ketonoxim-o-ether, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung als schädlingsbekämpfungsmittel

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