KR890012938A - 신규의 다이온 화합물과 그것의 용도 및 제조방법 - Google Patents

신규의 다이온 화합물과 그것의 용도 및 제조방법 Download PDF

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KR890012938A
KR890012938A KR1019890001047A KR890001047A KR890012938A KR 890012938 A KR890012938 A KR 890012938A KR 1019890001047 A KR1019890001047 A KR 1019890001047A KR 890001047 A KR890001047 A KR 890001047A KR 890012938 A KR890012938 A KR 890012938A
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South Korea
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compound
alkyl
group
phenyl
substituted
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KR1019890001047A
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제임스 엔더슨 리챠드
그리나 요나스
쿠넨 프레드
리 샤이-퓨
와이네류어 게리
슈나이더 헤르만
세킨져 칼
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크레머, 한스 루돌프 하우스
산도즈 리미티드
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Publication of KR890012938A publication Critical patent/KR890012938A/ko

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Abstract

내용 없음.

Description

신규의 다이온 화합물과 그것의 용도 및 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (52)

  1. 하기식 (I)의 화합물.
    상기식에서, R1,R2,R3및 R4는 독자적으로 최고 6개 탄소원자의 불포화 지방족 히드로카르빌기 : 최고 6개 탄소원자의 시클로알킬기 ; Ar 또는 (A1)nX 기이며 ; 따라서 R1,R2,R3및 R4중 하나가 C2-5알콜시카르보닐 일 수도 있으며 ; 최소한 R1,R2,R3및 R4중 하나가 (A1)nX이며 ; R2와 함께 R1또는 R4와 함께 R3가 또한 C2-5알킬렌 일 수 있으며, R1및 R2는 함께 옥소 또는 C1-5알킬리덴 기를 형성할 수도 있으며, Ar은 O,N 및 S로부터 선택된 1 내지 3개 헤테로원자를 포함한 비치환 또는 치환된 5- 또는 6-성분의 헤테로아릴이며, 환 탄소 원자에 의해 환 A에 결합되었으며, n은 0 또는 1이고, X는 H,OR6,SR7,NR8R9,R9,NO2,할로겐,CN,CF3,CHF2,S(O)mR10,CO-NHR11,CO-R12,CR13R14-COO(C1-6알킬) 또는 벤질이고, A1은 메틸렌 또는 에틸렌으로, 하나 이상의 C1-5알킬기로 치환 또는 비치환되었으며, R6및 R7은 독자적으로 H, 히드로카르빌, 할로알킬, 헤테로아릴 또는 기 CO-R15이며, R8은 H, 히드로카르빌, 헤테로아릴 또는 기 CO-R15이며, R9,R10,R1 zR14는 독자적으로 H, C1-6알킬 또는 아릴이며, R11은 H 또는 히드로카르빌이며, R12및 R15는 독자적으로 H, 히드로카르빌 또는 헤테로아릴이며, m은 1 또는 2이며, A2는 결합, CR16R17, CR16R17-CR18R19,O,S,NR20이거나 CO이며, R17및 R18은 독자적으로 H, 히드로카르빌 또는 유리형, 염형 또는 에스테르화형의 카르복실시 이며 따라서 근처 탄소 원자상에서 R1과 함께 R16는 결합을 형성할 수 있으며, R17및 R19는 독자적으로 H, 히드로카르빌 또는 (A1)nX 기이며, 여기에서 A1,n 및 X는 상기에 규정한 바이며, 그에 의해 R16및 R17또는 R18및 R19는 함께 (CH2)2-5기를 나타내기도 하며, 따라서 스피로 화합물을 형성하며 ; 및/또는 근처 탄소원자중 상에서 R16이 R1과 함께 또는 R18이 R3와 함께 (CH2)1-5를 형성하며 비시클릭 환을 형성하며, R24은 H, 히드로카르빌 또는 CO-R15이고, 여기에서 R15는 상기에 규정한 바이며, A3A4는 C=C(ORa) (기 A) 또는 C(X1)-C(O) (기 B)이며, X1은 F 또는 Cl이며, Ra는 H, 염 형성 부위 또는 그것이 결합된 산소화 함께 에테르 또는 에스테르 부위이며, Y는 R21,R22및 R23중 하나에 의해 치환된 페닐이거나, Ar′이며, Ar′은 O,S 및 N으로부터 선택된 1,2 또는 3개 헤테로원자를 포함한 5- 또는 6- 성분의 헤테로 원자기이며, 여기에서 헤테로 방향족 기는 치환 또는 비치환 되었으며, 환 탄소원자에 의해 그것이 결합한 C0-기에 연결되었으며, R21및 R22는 독자적으로 H, 할로겐, C1-4알킬, C1-4알콕시, C1-4할로알킬, CN,NO2,CF3O, RbS(O)p,NRcRd,C(O)-R,SO2-NRcRd또는 NRc-C(O)-Rd이며, 그에 의해 R21는 함께 메틸렌 디옥시 기를 형성할 수도 있고 P는 0,1 또는 2이며, Rb는 할로겐, 시아노, 페닐 또는 벤질에 의해 선택적으로 치환된 C1-4알킬이며, Rc및 Rd는 독자적으로 H 또는 C1-4알킬이고, Rㆍ는 C1-4알킬 또는 C1-4알콕시이며, R23은 할로겐, NO2,CN,C1-2알킬, C1-2알콕시, C1-2할로알킬 또는 C1-4알킬 -S(O)q이며, q는 0,1 또는 2인데, 상기 식에서, Y가 선택적으로 치환된 피리미디닐, 이외의 경우, R1,R2,R3및 R4중 하나는 페닐 또는 치환된 페닐이며, 하기 (a)(b) 및 (c)의 조건을 가짐. (a) R1,R2,R3및 R4중 하나에서 X는 H이며, 하기의 조건 (i) 내지 (vi)중 최소한 하나를 작용함. i) CR1R2-A2는 C(R2)=C(R17) 또는 CR1R2-CR16R17-CR18R19, ii) Y는 선택적으로 치환된 페닐, 또는 선택적으로 치환된 피리미디닐 이외의 것, iii) R1및 R2는 함께 옥소 또는 C1-5알킬리덴, iv) 기타 치환체 R1,R2,R3및 R4중 최소한 하나는 불포화 지방족 히드로카르빌기, 시클로알킬, 비치환 또는 치환된 페닐 또는 Ar, v) 기타 치환체 R1,R2,R3,R4,R17및 R19중 최소한 하나는 X가 H 이외의 것인 기(A1)nX, 또는 vi) A3A4는 C(X1)-C(O) (b) 상기식에서 CR1R2-A2는 C(R2)=C(R17)이고 R3및 R4는 둘다 H가 아니며, 및 (c) 상기식에서 R1및 R2는 함께 옥소이고, A2는 O,S,NR20또는 CO가 아님.
  2. 제1항에 있어서, R1은 최고 6개 탄소원자의 불포화 지방족기, 최고 6개 탄소원자의 시클로알킬기 또는 Ar이며, Ar은 제1항에서 규정된 바에 따르는 화합물.
  3. 제1항에 있어서, CR1-R2-A2는 C(R2)=CR17으로서 R2및 R17은 제1항에서 규정된 바에 따르는 화합물.
  4. 제1항에 있어서, R1및 R2가 함께 옥소 또는 C1-5알킬리덴인 화합물.
  5. 제1항에 있어서, A3A4는 C(X1)-C(O)이며, X1은 제1항에서 규정된 바에 따르는 화합물.
  6. 제1항에 있어서, R1은 CH3,C2H5, 비닐, 알릴, 프포파길, 시클로프로필, 선택적으로 치환된 페닐 ; 푸릴 ; 티에닐, (A1)nX′이거나 R2와 함께 옥소, CH2또는 CH-CH3기 또는 R17과 함께 결합을 이루며 ; n=0 또는 1 ; A1는 CH2또는 하나 또는 두개의 CH3기로 선택적으로 치환된 (CH2)2, 및 X′는 C1-4알카노일 ; OH 및 C2-5지방족 카르복실산 선택적으로 치환된 벤조산과 함께 그것의 에스테르 ; (C2-5카르브알콕시)-CH2; (C2-5카르브알콕시)-CH(CH3) ; 시아노, F,Cl,CHF2,CF3,NO2,CONH2,CONH(C1-4알킬), 디(C1-4알킬) N 또는 벤질 ; R2,R3및 R4중 하나는 H,C1-4알킬, C-1-4알콕시, C1-4알킬티오, OH,C1-4알킬 -CO-O,C2-5카르브알콕시, 티에닐 또는 푸릴 ; 및 R2,R3및 R4의 임의의 나머지 치환체는 H 또는 CH3인 화합물.
  7. 제6항에 있어서, A2는 결합, CH2,CH(CH3),C(CH3)2,CO,O,CH(CF3),CH2-CH2또는 CH(CH3)-(CH3)중 하나이거나, CR1R2와 함께 A2는 C(R2)=C(R17)이며, 여기에서 R17은 H,SCH3,CH3또는 CF3인 화합물.
  8. 제7항에 있어서, A2는 CH2,CH(CH3) 또는 C(CH3)2; (A1)nX′은 NO2, 티에닐 또는 푸릴이며 Y는 R21,R22및 R23에 의해 치환된 페닐인 화합물.
  9. 제7항에 있어서, n은 1 또는 2이고, Y는 R21,R22, 및 R23에 의해 치환된 페닐임을 특징으로 하는 화합물.
  10. 제1 내지 제7항중 어느 한 항에 있어서, Y는 R21,R22및 R23에 의해 치환된 페닐이거나 티에닐, 피라졸릴, 이소티아졸릴, 피리딜, 피라지닐 또는 피리미디닐이며, 헤테로 방향족기는 메틸렌 디옥시, NO2,할로겐,CN,CF3,CH3-SO2또는 CH3SCH2에 의해 O-치환되었으며, 선택적으로 환탄소 원자에 결합한 C1-4알킬과 할로겐 및 환 N-원자에 결합한 C1-4알킬, 벤질 및 C1-4알킬티오-C1-4알킬로부터 선택된 1 또는 2개의 부가치환체를 가지며 ; R22는 카르보닐기의 P-위치에 있으며, H, 할로겐, C1-4알킬, -S, C1-4알킬-SO2이고, R23은 카르보닐기의 O-위치에 있으며, 할로겐,CF3,NO2,CN 또는 CH3SO2이고 R21은 H, 할로겐 또는 CH3인 화합물.
  11. 제10항에 있어서, Y가 R21,R22및 R23으로 치환된 페닐인 화합물.
  12. 제10항에 있어서, Y가 피라졸릴, 피리미디닐 또는 피리닐인 화합물.
  13. 제12항에 있어서, Y가 치환된 피라졸릴인 화합물.
  14. 제12항에 있어서, Y가 치환된 피리딜인 화합물.
  15. 제1항에 있어서, R1이 H, CH3,SCH3,S(O)CH3,SO2CH3페닐 또는 C1-4알킬, C1-4알콕시, 할로겐 또는 CF3로 일치환된 페닐이거나 최고 4개 탄소원자의 알케닐 또는 알키닐인 화합물.
  16. 제1항 또는 제15항에 있어서, R2,R3및 R4가 독자적으로 H 또는 CH3이고 또한 R2내지 R4중 단 하나가 SCH3,S(O)CH3또는 SO2CH3인 조건으로, R2,R3및 R4중 하나는 SCH3,S(O)CH3또는 SO2(CH3)인 화합물.
  17. 제16항에 있어서, A2가 CH(CF3),CH2또는0인 화합물.
  18. 제17항에 있어서, Y가 3,5-디클로로-2-피리딜인 화합물.
  19. 제17항에 있어서, Y가 1-CH3-4-NO2-피라졸-5-일 또는 1-CH3-4-NO-피라졸-3-일인 화합물.
  20. 제17항에 있어서, Y가 R21,R22및 R23으로 치환된 페닐이며, 여기에서 R21,R22및 R23은 제1항에서 규정되어 있는 화합물.
  21. 제15항에 있어서, R1은 SCH3,S(O)CH3또는 SO2CH3; R2,R3및 R4는 독자적으로 H 또는 CH3; A2는 CH2,O 또는 CH(CF3) ; 및 Y는 3,5-디클로로-2-피리딜, 1-CH3-4-NO2-피라졸-5-일, 1-CH3-4-NO2-피라졸-3-일 또는 R21,R22및 R23에 의해 치환된 페닐인 화합물.
  22. 제21항에 있어서, A2는 CH(CF3) 또는 0이고 Y는 R21,R22및 R23으로 치환된 페닐인 화합물.
  23. 제15항에 있어서, R1은 최고 4개 탄소원자의 알케닐 또는 알키닐 : R2,R3및 R4는 독자적으로 H,CH3,SCH3,S(O)CH3또는 SO2CH3이며, 단 R2내지 R4중 단 하나는 SCH3,S(O)CH3및 SO2CH3로부터 선택되며, A2는 CH2,O 또는 CH(CF3) ; 및 Y는 3,5-디클로로-2-피리딜, 1-CH3-4-NO2-피라졸-5-일, 1-CH3-4-NO2-피라졸-3-일 또는 R21,R22및 R23에 의해 치환된 페닐인 화합물.
  24. 제15항에 있어서, R21은 페닐 또는 C1-4알킬, C1-4알콕시, 할로겐 또는 CF3로 일치환된 페닐 ; R2,R3및 R4는 독자적으로 H 또는 CH3; A2는 CH(CF3),CH2또는 0 ; 및 Y는 3,5-디클로로-2-피리딜, 1-CH3-4-NO2-피라졸-5-일, 1-CH3-4-NO2-피라졸-3-일 또는 R21,R22및 R23으로 치환된 페닐인 화합물.
  25. 제24항에 있어서, Y는 R21,R22및 R23으로 치환된 페닐인 화합물.
  26. 제1항 내지 제25항중 어느 한 항에 있어서, A3A4가 C=C(ORa)인 화합물.
  27. 2-(1-메틸-4-니트로-5-피라졸릴 카르보닐)-1,3-시클로헥산다이온.
  28. 2-(1-메틸-4-니트로-5-피라졸릴카르보닐)-1,3-시클로헥산다이온.
  29. 2-(1-메틸-4-니트로-5-피라졸릴카르보닐)-5-메틸-1,3-시클로헥산다이온.
  30. 2-(1-메틸-4-니트로-5-피라졸릴카르보닐)-4,4,6-트리메틸--1,3-시클로헥산다이온.
  31. 2-(1-메틸-4-니트로-5-피라졸릴카르보닐)-4,4,6,6-테트라메틸-1,3-시클로헥산다이온.
  32. 4-(1-메틸-4-니트로-5-피라졸릴카르보닐)-2,2,6,6-테트라메틸-3,6-디히드로-2H-피란-3-온.
  33. 2-(4-클로로-2-니트로벤조일)-4-페닐-1,3-시클로헥산다이온.
  34. 2-(4-클로로-2-니트로벤조일)-5-트리플루오로메틸-1,3-시클로헥산다이온.
  35. 2-(4-클로로-2-니트로벤조일)-4-메틸-5-트리플루오로메틸-1,3-시클로헥산다이온.
  36. 2-(4-클로로-2-니트로벤조일)-4,4-디메틸-5-트리플루오로메틸-1,3-시클로헥산다이온.
  37. 2-(4-클로로-2-니트로벤조일)-4-(2-플루오로페닐-1,3-시클로헥산다이온.
  38. 2-(4-클로로-2-니트로벤조일)-4-(4-플루오로페닐-1,3-시클로헥산다이온.
  39. 2-(2-시클로-4-메틸설포닐벤조일)-5-트리플루오로메틸-1,3-시클로헥산다이온.
  40. 2-(4-시클로-2-니트로벤조일)-4,6,6-트리메틸-4-시클로헥산다이온.
  41. 2-클로로-2-(4-클로로-2-니트로벤조일)-4,4,6,6-테트라메틸-1,3-시클로헥산다이온.
  42. 2-클로로-2-(4-클로로-2-니트로벤조일)-4,4,6-트리메틸-1,3-시클로헥산-1,3-다이온.
  43. 2-(3,5-디클로로-2-피리딜카르보닐)-1,3-시클로헥산다이온.
  44. 제26항에 있어서, Ra가 H인 형태 또는 염 형태의 화합물.
  45. 유리형태 또는 염형태의 제27항 내지 43항중 어느 한 항에 따른 화합물.
  46. 2-(1-메틸-4-니트로-3-피라졸릴카르보닐-3-(페녹시카르보닐옥시)-2-시클로헥센-1-온.
  47. 제26항에 있어서, Ra가 결합된 산소와 함께 에테르 또는 에스테르 부위를 형성하는 화합물.
  48. 하기식 (II)의 화합물을 하기식 (III)의 화합물과 반응시킨 후, 산출된 하기식 (IV)의 에스테르의 전위로 하기 식 (Ib)의 화합물을 산출하고, 산출된 식 (Ib)의 화합물을 대응하는 2-(Y-CO)-2-엔-1-온-3-올 에테르, 2-(Y-CO)-2-엔-1-온-3-올을 에스테르 또는 2-X1-2-(YCO)-1,3-다이온 화합물로 선택적으로 에테르화, 에스테르화 또는 할로겐화 하는 것을 포함하는 제1항에서 언급된 식 (I)의 화합물을 제조하는 방법.
    상기식에서, Y,A2,R1,R2,R3및 R4는 상기에서 규정하였으며, Hal은 할로겐이고 M은 H 또는 염형성 부위임.
  49. 제48항에 있어서, 본 명세서에서 거의 기술된 실시예의 방식에 의한 방법.
  50. 제48항 또는 제49항에 의한 방법으로 산출된 식 (I)의 화합물.
  51. 제1항 내지 제47항 또는 제50항중 어느 한 항에 의한 식 (I)의 화합물을 포함한 제초성 조성물.
  52. 제1항 내지 제47항 또는 제50항중 어느 한 항에 의한 식 (I) 화합물의 제초적으로 유효한 양을 잡초 또는 그 위치에 적용하여 잡초를 제거하는 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019890001047A 1988-02-01 1989-01-31 신규의 다이온 화합물과 그것의 용도 및 제조방법 KR890012938A (ko)

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