KR950011389A - 디할로프로펜 화합물, 활성성분으로서 상기 디할로프로펜 화합물을 함유한 살충제/살진드기제 및 상기 디할로프로펜 화합물 제조용의 중간체 화합물 - Google Patents

디할로프로펜 화합물, 활성성분으로서 상기 디할로프로펜 화합물을 함유한 살충제/살진드기제 및 상기 디할로프로펜 화합물 제조용의 중간체 화합물 Download PDF

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KR950011389A
KR950011389A KR1019940026769A KR19940026769A KR950011389A KR 950011389 A KR950011389 A KR 950011389A KR 1019940026769 A KR1019940026769 A KR 1019940026769A KR 19940026769 A KR19940026769 A KR 19940026769A KR 950011389 A KR950011389 A KR 950011389A
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trifluoromethyl
compound
halogen
dihalopropene
alkyl
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노리야스 사까모또
마사야 스즈끼
도시오 나가또미
가즈노리 쓰시마
기미또시 우메다
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고오사이 아끼오
스미또모가가꾸고오교 가부시끼가이샤
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Publication of KR950011389A publication Critical patent/KR950011389A/ko

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Abstract

하기 식 I의 디할로프로펜 화합물이 개시되어 있다.
(식중, ℓ은 1 내지 5의 정수이며; m은 1 내지 4의 정수이고; R1들 및 R2들은 같거나 다르며, 독립적으로 할로겐 또는 여러 기들이며; D는 산소이고; X들은 같거나 다르고 독립적으로 염소 또는 브롬이며; Y는 산소이고; Z, P 및 Q은 같거나 다르고 독립적으로 질소 또는 CH이고, 단 P와 Q은 동시에 질소가 될수 없고, Y가 황일 경우 Z는 CH이다). 또한 활성 성분으로서 디할로프로펜 화합물을 함유한 살충제/살진드기제가 개시되어 있다. 본 디할로프로펜 화합물은 뛰어난 살충/살진드기 활성을 나타낸다. 또한, 상기 디할로프로펜 화합물의 제조에 사용할 수 있는 중간체 화합물이 개시되어 있다.

Description

디할로프로펜 화합물, 활성성분으로서 상기 디할로프로펜 화합물을 함유한 살충제/살진드기제 및 상기 디할로프로펜 화합물 제조용의 중간체 화합물
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (33)

  1. 하기 식 I의 디할로프로펜 화합물 :
    (식중, ℓ은 1 내지 5의 정수이며; m은 1 내지 4의 정수이고; R1은 할로겐, 시아노, 아세트아미도, 트리플루오로아세트아미도, 니트로, C1∼C8알킬, C1∼C3할로알킬, C1∼C7알콕시, C1∼C3할로알콕시, C1∼C3알킬티오, C1∼C3할로알킬티오, C3∼C6알케닐옥시 C3∼C6할로알케닐옥시, C1∼C8히드록시알킬, C1∼C4알케닐, C2∼C4할로알케닐, C2∼C4알키닐, C2∼C4할로알키닐, C3∼C6알키닐옥시, C3∼C6할로알키닐옥시, C2∼C4알콕시알킬, C2∼C4알킬티오알킬, C3∼C6시클로알킬, C5∼C6시클로알케닐, C3∼C6시클로알킬옥시, C5∼C6시클로알케닐옥시, 페닐, 피리딜옥시, 페녹시 또는 벤질이며, 이들 중 마지막 네개는 할로겐, C1∼C5알킬, C1∼C3알콕시, C1∼C3할로알킬 또는 C1∼C3할로알콕시로 임의로 치환될 수 있는데 단, ℓ이 2 내지 5의 정수일 경우, R1들은 같거나 다르며, 또는 두개의 인접한 R1들은 그들 말단에서 함께 결합하여 트리메틸렌, 테트라메틸렌, 메틸렌디옥시, 에틸렌디옥시 또는 CH=CH-CH=CH를 형성할 수 있고; R2은 할로겐, C1∼C5알킬, C1∼C3할로알킬, C1∼C3알콕시, C1∼C3할로알콕시, C1∼C4알케닐, C2∼C4할로알케닐, C2∼C4알콕시알킬 C2∼C4알콕시아미노, 알릴옥시이미노, 니트로, 또는 할로겐, 알킬 또는 C1∼C3알콕시로 임의로 치환될 수 있는 페닐이며, 단 m이 2 내지 4의 정수일 경우, R2들은 같거나 다르며, 또는 인접한 두개의 R2들은 그들의 말단에서 함께 결합하여 트리메틸렌 또는 테트라메틸렌을 형성할 수 있고; D는 산소, NH 또는 황이며; X들은 같거나 다르고, 독립적으로 염소이거나 브롬이고; Y가 산소, NR3, S(O)q, C(R4)2, C=C(R4)2또는 C(CH3)2이며 (여기서, R3은 수소, C1∼C2알킬, 트리플루오로아세틸 또는 아세틸이고, R4들은 같거나 다르고 옥립적으로 수소이거나 C1∼C3알킬이고, q는 0 내지 2의 정수이다) : Z, P 및 Q는 같거나 다르고 독립적으로 질소 또는 CH인데, 단 P와 Q가 동시에 질소가 될수 없고, Y가 황일 경우 Z은 CH이다).
  2. 제1항에 있어서, R1이 할로겐, C1∼C8알킬, C1∼C3할로알킬, C1∼C7알콕시, C1∼C3할로알콕시, C3∼C6알케닐옥시 C3∼C6할로알케닐옥시, C3∼C6시클로알킬, 페닐, 피리딜옥시, 페녹시 또는 벤질이며, 이들 중 마지막 네개는 할로겐, C1∼C5알킬, C1∼C3알콕시, C1∼C3할로알킬 또는 C1∼C3할로알콕시로 임의로 치환될 수 있는데 단, ℓ이 2 내지 5의 정수일 경우, R1들은 같거나 다르며, 또는 두개의 인접한 R1들은 그들의 말단에서 함께 결합하여 트리메틸렌, 테트라메틸렌, 메틸렌디옥시, 에틸렌디옥시 또는 CH=CH-CH=CH를 형성할 수 있으며; R2가 할로겐, 니트로, C1∼C5알킬, C1∼C3할로알킬, C4∼C4알케닐, C2∼C4할로알케닐, C2∼C4알키닐, C2∼C4알콕시알킬, C2∼C4알콕시이미노, 알릴옥시이미노 또는 할로겐, C1∼C5알킬 또는 C1∼C3알콕시로 임의로 치환될 수 있는 페닐이고, 단 m이 2 내지 4의 정수일 경우, R2들은 같거나 다르며, 또는 인접한 두개의 R2들은 그들의 말단에서 함께 결합하여 트리메틸렌 또는 테트라메틸렌을 형성할 수 있으며; D가 산소이고; X들이 같거나 다르고, 독립적으로 염소 또는 브롬이며; Y는 산소, NR3, 황 또는 C(R4)2이고 (여기서, R3은 수소 또는 C1∼C2알킬이고, R4들은 같거나 다르고 독립적으로 수소 또는 C1∼C3알킬이다); Z가 질소 또는 CH이고, 단 Y가 황일 경우 Z가 CH이며; P 및 Q가 CH인 디할로프로펜 화합물.
  3. 제1항에 있어서, Z가 CH일 경우 R1이 할로겐, C1∼C8알킬, 트리플루오로메틸, C1∼C2할로알콕시, C1∼C4알콕시, C3∼C6알케닐옥시, C3∼C6할로알케닐옥시, 시클로헥실, 시클로펜틸, 페닐, 페녹시, 또는 할로겐, C1∼C4알킬 또는 트리플루오로메틸로 임의로 치환될 수 있는 피리딜옥시이고, 단 ℓ이 2 또는 3의 정수인 경우, R1들은 같거나 다르며, 또는 두개의 인접한 R1들은 그들 말단에서 함께 결합하여 트리메틸렌, 테트라메틸렌, 메틸렌디옥시, 에틸렌디옥시 또는 CH=CH-CH=CH를 형성할 수 있으며; Z가 질소인 경우, R1이 할로겐, 트리플루오로메틸, C3∼C4알케닐, C3∼C4할로알케닐, 에티닐, 메톡시메틸, 니트로, C1∼C2알콕시이미노, 알릴옥시이미노 또는 페닐이며, 단 m이 2 또는 3의 정수일 경우, R2들은 같거나 다르며, 또는 인접한 두개의 R2들은 그들의 말단에서 함께 결합하여 테트라메틸렌을 형성할 수 있고; D가 산소이며; X들은 같거나 다르고, 독립적으로 염소 또는 브롬이고; Z가 CH일 경우, Y가 산소, NR3, 황 또는 C(CH3)2이며 (여기서, R3는 상기에서 정의된 것과 같다). Z가 질소일 경우, Y가 산소 또는 NH이고; P와 Q가 CH인 디할로프로펜 화합물.
  4. 제1항에 있어서, Z가 CH일 경우, ℓ이 1 내지 3의 정수이고, R1이 할로겐, C1∼C2할로알킬, C3∼C4알킬, C1∼C4알콕시, C2∼C3할로알콕시, 시클로헥실, 시클로펜틸, 페닐, 또는 페녹시이고, 단 ℓ이 2 또는 3의 정수일 경우, R1들은 같거나 다르며, 또는 두개의 인접한 R1들은 그들 말단에서 함께 결합하여 테트라메틸렌, 메틸렌디옥시 또는 CH=CH-CH=CH을 형성할 수 있고, R2가 할로겐, 트리플루오로메틸, 알릴 또는 C3알킬이며; 그리고 Z가 질소인 경우, m은 1 내지 2의 정수이고, R1이 할로겐 또는 트리플루오로메틸이고, R2가 할로겐 또는 메틸이고, 단 m이 1 또는 2의 정수일 경우, R2들은 같거나 다르며; D가 산소이고; X들은 같거나 다르고 독립적으로 염소 또는 브롬이고; Z가 CH일 경우, Y가 산소, 황 또는 C(CH3)2이고, Z가 질소일 경우, Y가 산소 또는 NH이며; P와 Q가 CH인 디할로프로펜 화합물.
  5. 제4항에 있어서, 2-트리플루오로메틸-4-(4-이소프로폭시페녹시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠인 디할로프로펜 화합물.
  6. 제4항에 있어서, 2-트리플루오로메틸-4-(4-이소프로폭시페녹시)-1-(3,3-디브로모-2-프로페닐옥시)벤젠인 디할로프로펜 화합물.
  7. 제4항에 있어서, 2-브로모-4-(1-메틸-1-(4-이소프로폭시페닐)에틸)-1-(3,3-디브로모-2-프로페닐옥시)벤젠인 디할로프로펜 화합물.
  8. 제4항에 있어서, 2-트리플루오로메틸-4-(4-시클로헥실페녹시)-1-(3,3-디브로모-2-프로페닐옥시)벤젠인 디할로프로펜 화합물.
  9. 제4항에 있어서, 2-트리플루오로메틸-4-(4-시클로헥실페녹시)-1-(3,3-디브로모-2-프로페닐옥시)벤젠인 디할로프로펜 화합물.
  10. 제4항에 있어서, 2-트리플루오로메틸-4-(2,6-디클로로-4-트리플루오로메틸페녹시)-1-(3,3-디브로모-2-프로페닐옥시)벤젠인 디할로프로펜 화합물.
  11. 제4항에 있어서, 2-트리플루오로메틸-4-(5,6,7-테트라히드로-2-나프틸옥시)-1-(3,3-디브로모-2-프로페닐옥시)벤젠인 디할로프로펜 화합물.
  12. 제4항에 있어서, 2-n-프로필-4-(4-이소프로폭시페녹시)-1-(3,3-디클로로-2-프로페닐옥시)벤젠인 디할로프로펜 화합물.
  13. 제4항에 있어서, 2-n-프로필-4-(4-이소프로폭시페녹시)-1-(3,3-디브로모-2-프로페닐옥시)벤젠인 디할로프로펜 화합물.
  14. 제4항에 있어서, 3,5-디클로로-4-(3-클로로-5-트리플루오로메틸-2-피리딜옥시)-1-3,3-디클로로프로페닐옥시)벤젠인 디할로프로펜 화합물.
  15. 제4항에 있어서, 3,5-디클로로-4-(3-브로모-5-트리플루오로메틸-2-피리딜옥시)-1-3,3-디클로로프로페닐옥시)벤젠인 디할로프로펜 화합물.
  16. 제4항에 있어서, 3,5-디클로로-4-(3,5-비스트리플루오로메틸-2-피리딜옥시)-1-(3,3-디클로로프로페닐옥시)벤젠인 디할로프로펜 화합물.
  17. 제4항에 있어서, 2,6-디클로로-4-(3-클로로-5-트리플루오로메틸-2-피리딜아미노)-1-(3,3-디브로모-2-프로페닐옥시)벤젠인 디할로프로펜 화합물.
  18. 활성 성분으로서 제1항에 따른 디할로프로펜 화합물을 함유한 살충제/살진드기제.
  19. 해충이 서식하는 장소에 제1항에 따른 디할로프로펜 화합물을 유효량 살포하는 해충 방제 방법.
  20. 활성 성분으로서 제1항에 따른 디할로프로펜 화합물의 용도.
  21. 하기식 Ⅱ의 화합물을 하기식 Ⅲ의 화합물과 반응시킴을 특징으로 하는 제1항에 따른 디할로프로펜 화합물의 제조 방법 :
    (식들 중, R1, R2, Y, D, Z, P, Q, ℓ, m 및 X은 각각 제1항에서 정의된 것과 같고, L은 할로겐, 메실옥시 또는 토실옥시이다).
  22. 탈수제의 존재하에 불활성 용매중에서 하기식 Ⅱ의 화합물과 하기식 Ⅳ의 알콜 화합물을 반응시킴을 특징으로 하는 제1항에 따른 디할로프로펜 화합물의 ㅈ조방법 :
    (식중, R1, R2, Y, D, Z, P, Q, ℓ, m 및 X은 각각 제1항에서 정의된 것과 같다).
  23. 하기 식의 중간체 화합물 :
    (식중, ℓ은 1 내지 5의 정수이고; R1은 할로겐, C1∼C8알킬, 트리플루오로메틸, C1∼C4알콕시, C1∼C2할로알킬티오, C3∼C5알케닐옥시, C3∼C4할로알케닐옥시, C3∼C6시클로알킬, 페닐, 피리딜옥시, 페녹시 또는 벤질이며, 이들 중 마지막 네개는 할로겐, C1∼C5알킬, C1∼C3알콕시, C1∼C3할로알킬 또는 C1∼C3할로알콕시로 임의로 치환될 수 있는데 단, ℓ이 2 내지 5의 정수일 경우, R1들은 같거나 다르며, ℓ이 1 내지3의 정수일 경우 두개의 인접한 R1들은 그들 말단에서 함께 결합하여 트리메틸렌, 테트라메틸렌, 메틸렌디옥시, 에틸렌디옥시 또는 CH=CH-CH=CH를 형성할 수 있다).
  24. 하기 식의 중간체 화합물 :
    (식에서, R1은 할로겐 또는 트리플루오로메틸이고; R2및 R2'는 같거나 다르며, 독립적으로 불소, 염소, 트리플루오로메틸 또는 메틸이다).
  25. 하기 식의 중간체 화합물 :
    (식에서, R1은 할로겐 또는 트리플루오로메틸이고; R2들은 같거나 다르며, 독립적으로 할로겐, 트리플루오로메틸 또는 C1~C3알킬이고; 그리고 m은 1 내지 4의 정수이다).
  26. 제23항에 있어서, 2-트리플루오로메틸-4-(4-이소프로폭시페녹시)페놀인 중간체 화합물.
  27. 제23항에 있어서, 2-트리플루오로메틸-4-(4-시클로헥실페녹시)페놀인 중간체 화합물.
  28. 제23항에 있어서, 2-트리플루오로메틸-4-(2,6-디클로로-4-트리플루오로메틸페녹시)페놀인 중간체 화합물.
  29. 제23항에 있어서, 2-트리플루오로메틸-4-(5,6,7,8-테트라히드로-2-나프틸옥시)페놀인 중간체 화합물.
  30. 제24항에 있어서, 3,5-디클로로-4-(3-클로로-5-트리플루오로메틸-2-피리딜옥시)페놀인 중간체 화합물.
  31. 제24항에 있어서, 3,5-디클로로-4-(3-브로모-5-트리플루오로메틸-2-피리딜옥시)페놀인 중간체 화합물.
  32. 제24항에 있어서, 3,5-디클로로-4-(3,5-비스트리플루오로메틸-2-피리딜옥시)페놀인 중간체 화합물.
  33. 제25항에 있어서, 2,6-디클로로-4-(3-클로로-5-트리플루오로메틸-2-피리딜아미노)페놀인 중간체 화합물.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019940026769A 1993-10-19 1994-10-19 디할로프로펜 화합물, 활성성분으로서 상기 디할로프로펜 화합물을 함유한 살충제/살진드기제 및 상기 디할로프로펜 화합물 제조용의 중간체 화합물 KR950011389A (ko)

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CN1108642A (zh) 1995-09-20
BR9404147A (pt) 1995-06-13
IL111252A0 (en) 1994-12-29
US5698702A (en) 1997-12-16
TW306864B (ko) 1997-06-01
DE69411658D1 (de) 1998-08-20
ZA948162B (en) 1995-06-19
CA2118349A1 (en) 1995-04-20
CN1080251C (zh) 2002-03-06
ES2119046T3 (es) 1998-10-01
RU94037561A (ru) 1996-09-10
TR28760A (tr) 1997-02-28
EP0648729B1 (en) 1998-07-15
EG20417A (en) 1999-02-28
EP0648729A1 (en) 1995-04-19
AU675580B2 (en) 1997-02-06
RU2130008C1 (ru) 1999-05-10
DE69411658T2 (de) 1999-02-25
US5530015A (en) 1996-06-25
AU7588094A (en) 1995-05-11

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