KR940011414A - 살충제로서 유용한 n'-치환된-n,n'-디아실히드라진류 화합물 및 이를 함유하는 조성물과 그들의 사용방법 - Google Patents

살충제로서 유용한 n'-치환된-n,n'-디아실히드라진류 화합물 및 이를 함유하는 조성물과 그들의 사용방법 Download PDF

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KR940011414A
KR940011414A KR1019930025020A KR930025020A KR940011414A KR 940011414 A KR940011414 A KR 940011414A KR 1019930025020 A KR1019930025020 A KR 1019930025020A KR 930025020 A KR930025020 A KR 930025020A KR 940011414 A KR940011414 A KR 940011414A
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tert
butylhydrazine
methylbenzoyl
methoxy
dimethylbenzoyl
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KR100317793B1 (ko
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리더트 제브
유진 호만 로버트
패트 리 대트
랜슨 오피 토마스
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윌리엄 이. 램버트 3세
롬 앤드 하스 캄파니
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Abstract

본 발명은 N-(2-Ra-3-Rb-4-Rh-벤조일)-N′-(2-Rc-3-Rd-4-Re-5-Rf-벤조일)-N′-Rg을 히드라진을 갖는 살충화합물 뿐만 아니라 농경학적으로 수용할만한 캐리어(carrier) 및 이와 같은 화합물의 살충유효양을 함유하는 조성물; 및 이와같은 화합물 및 조성물의 사용 방법에 관한 것이다.
단, 상기 식에서 Ra는 할로 또는 저급 알킬; Rb는 저급알콕시 혹은 임의적으로 할로(바람직하게는 플루오르)로 치환된 저급 알콕시; Rc는 수소, 할로, 저급알킬, 저급 알콕시, 및 니트로로부터 선택되면; Rd, Re및 Rf는 수소, 브로모, 클로로, 플루오로, 저급 알킬, 저급 알콕시, 및 저급 알콕시 저급 알킬로부터 각각 독립적으로 선택되며; Rg는 (C4-C6)알킬; Rh는 수소, 저급 알콕시, 저급 알킬, 또는 Rb와 함께 취할때는 옥소원자가 Rb위치에 있는 메틸렌디옥시(-OCH2O-), 1,2-에틸렌디옥시(OCH2CH2O-), 1,2-에틸렌옥시(-CH2CH2O-), 또는 1,3-프로필렌옥시(-CH2CH2CH2O-)이며; 치환기 Rc또는, Rd과 Re, 또는 Re와 Rf을 함께 취할때는 메틸렌디옥시 또는 1,2-에틸렌디옥시일 수 있다.
또한, 본 발명은 3-아미노-2-(치환된)-벤조산, 소디움 나이트리트 및 산성조건하의 메탄올을 혼합하는 단계 또는 3,4-융합된 헤테로고리 벤조산 및 알킬 리튬 시약을 혼합한 후 친전자성 시약과 후속적으로 반응함을 포함하는 화합물 및 그들의 중간체 생성방법에 관한 것이다.

Description

살충제로서 유용한 N′-치환된 -N,N′-디아실히드라진류 화합물 및 이를 함유하는 조성물과 그들의 사용방법
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Claims (55)

  1. 식 N-(2-Ra-3-Rb-4-Rh-벤조일)-N′-(2-Rc-3-Rd-4-Re-5-Rf-벤조일)-N′-Rg을 히드라진을 갖는 살충화합물. 단, 상기 식에서 Ra는 할로 또는 저급 알킬; Rb는 저급 알콕시 또는 할로로 치환된 저급 알콕시; Rc는 수소, 할로, 저급 알킬, 저급알콕시, 저급알콕시 저급알킬, 및 니트로로 부터 선택되며; Rd,Re및 Rf는 수소, 브로모, 클로로, 플루오로, 저급알킬, 저급알콕시, 및 저급 알콕시 저급 알킬로부터 각각 독립적으로 선택되며; Rg는 (C4-C6)알킬; Rh는 수소, 저급 알콕시, 저급 알킬, 또는 Rb와 함께 취할때는 옥시원자가 Rb자리에 위치한 메틸렌디옥시, 1,2-에틸렌디옥시 1,2-에틸렌옥시 또는 1,3-프로필렌옥시이며; 치환기 Rc와 Rd과 Re, 또는 Re와 Rf를 함께 취할때는 메틸렌디옥시 또는 1,2-에틸렌디옥시일 수 있다.
  2. 제1항에 있어서, Ra는 브로모, 클로로, 또는 (C1-C3)알킬이며; Rb는 (C1-C4)알콕시; Rc는 수소, 브로모, 클로로, 플루오로, (C1-C3)알킬, (C1-C4)알콕시, (C1-C2)알콕시 (C1-C2)알킬 및 니트로로부터 선택되며; Rd,Re및 Rf는 수소, 브로모, 클로로, 플루오로, (C1-C3)알킬, (C1-C4)알콕시, 및 (C1-C2)알콕시, (C1-C2)알킬로부터 각각 독립적으로 선택되며; Rg는 (C4-C6)알킬; Rh는 수소, (C1-C2)알콕시, (C1-C2)알킬, 또는 Rb와 함께 취할때는 메틸렌디옥시 또는 1,2-에틸렌디옥시이고; 치환기 Rc와 Rd, 또는 Rd와 Re, 또는 Re와 Rf를 함께 취할때는 메틸렌디옥시 또는 1,2-에틸렌디옥시일 수 있음을 특징으로 하는 살충화합물.
  3. 제2항에 있어서, Ra는 브로모, 클로로, 메틸 또는 에틸이며; Rb는 메톡시, 트리플루오로메톡시 또는 에톡시이며; Rc,Rd,Re및 Rf는 수소, 브로모, 클로로, 플루오로, 메틸, 메톡시 및 메톡시메틸로부터 각각 독립적으로 선택되며, Rg는 tert-부틸, 네오펜틸 또는 메틸네오펜틸임을 특징으로 하는 살충화합물.
  4. 제3항에 있어서, Ra는 메틸 또는 에틸이고; Rb는 메톡시 또는 에톡시이며; Rc,Rd,Re및 Rf는 수소, 브로모, 클로로, 플루오로, 메틸 및 메톡시로부터 각각 독립적으로 선택되며; Rg는 tert-부틸이고; Rh는 수소 또는 Rb와 함께 취할때는 메틸렌디옥시 또는 1,2-에틸렌디옥시임을 특징으로 하는 살충화합물.
  5. 제4항에 있어서, Rb는 메톡시, 또는 Rh와 함께 취할때는 메틸렌디옥시 또는 1,2-에틸렌디옥시이고, Rc,Rd,Re및 Rf중 셋 이하만이 브로모, 클로로, 플루오로, 및 메틸로 구성되는 그룹에서 선택된 같은 요소이거나, Rd,Re및 Rf중 둘이하만이 메톡시임을 특징으로 하는 살충화합물.
  6. 제5항에 있어서, Rc,Rd,Re및 Rf중 셋이하만이 클로로, 플루오로, 메톡시 및 메틸로부터 독립적으로 선택되고 나머지 Rc,Rd,Re및 Rf는 수소임을 특징으로 하는 살충화합물.
  7. 제6항에 있어서, Rd및 Rf는 클로로,메톡시 및 메틸로부터 독립적으로 선택되고 Rc및 Re는 모두 수소임을 특징으로 하는 살충화합물.
  8. 제7항에 있어서, Rd및 Rf는 브로모, 클로로, 및 플루오로로부터 각각 독립적으로 선택됨을 특징으로 하는 살충화합물.
  9. 제8항에 있어서, Rd및 Rf는 각각 클로로임을 특징으로 하는 살충화합물.
  10. 제7항에 있어서, Rd및 Rf는 메틸 및 메톡시로부터 각각 독립적으로 선택됨을 특징으로하는 살충화합물.
  11. 제10항에 있어서, Rd및 Rf는 각각 메틸임을 특징으로하는 살충화합물.
  12. 제7항에 있어서, Rd는 브로모, 클로로 및 플루오로로부터 선택되고, Rf는 메틸 및 메톡시로부터 선택됨을 특징으로 하는 살충화합물.
  13. 제12항에 있어서, Rd는 클로로이고 Rf는 메틸임을 특징으로 하는 살충화합물.
  14. 제5항에 있어서, Rc는 클로로, 플루오로, 및 메톡시로부터 선택되고; Rd는 수소임을 특징으로 하는 살충화합물.
  15. 제14항에 있어서, Rc는 클로로이고 Rf는 메틸 또는 메톡시임을 특징으로 하는 살충화합물.
  16. 제5항에 있어서, Rc는 클로로이고 Rd는 클로로임 특징으로 하는 살충화합물.
  17. 제4항에 있어서, Rc는 수소, Rd는 수소이며, Re는 클로로이며, Rf는 수소임을 특징으로 하는 살충화합물.
  18. 제4항에 있어서, Rc는 수소, Rd는 메틸, Re는 수소, 그리고 Rf는 수소임을 특징으로 하는 살충화합물.
  19. 제4항에 있어서, Rc는 수소, Rd는 수소, Re는 수소, Rf는 수소임을 특징으로 하는 살충화합물.
  20. 제1항 또는 제2항에 있어서, N-(3-메톡시-2-메틸벤조일)-N′-(3-클로로-5-메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(2,4-디클로로벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3-메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-벤조일-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(4-클로로벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3,4,5-트리클로로벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3,4-디클로로벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3-메톡시-5-메틸벤조일)-N′-tert-부틸히드라진, N-(메톡시-2-메틸벤조일)-N′-(4-플루오로벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3-메톡시-4-메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3,4-디메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3-메톡시벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(4-클로로-3-메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(4-클로로-2-메틸벤조일)-N′tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3-브로모-5-메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3-브로모-5-클로로벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3,5-디플루오로벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(4-메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3-클로로-4-플루오로벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3-플루오로벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3,4-플루오로벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(2-메톡시-4-메틸벤조일)-N′-tert-부틸히드라진, N-(3-에톡시-2-메틸벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3-클로로벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(2-클로로-5-메틸벤조일)-N′-tert-부틸히드라진,N-(2-브로모-3-메톡시벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(2-클로로-3-메톡시벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(2-메틸-3-트리플루오르메틸벤조일-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진,N-(3-메톡시-2-메틸벤조일)-N′-(3-브로모-4-플루오로벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(4-플루오로-3-메틸벤조일-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3-클로로-4-메틸벤조일)-N′-tert-부틸히드라진, N-(-3-메톡시-2-메틸벤조일)-N′-(3-클로로-4-에톡시벤조일)-N′-tert-부틸히드라진, N-(-3-메톡시-2-메틸벤조일)-N′-(3-에틸벤조일)-N′-tert-부틸히드라진, N-(2-에틸-3-메톡시벤조일)-N′-(2,5-디플루오로벤조일)-N′-tert-부틸히드라진, N-(2-에틸-3-메톡시벤조일)-N′-(3-메톡벤조일)-N′-tert-부틸히드라진, N-(2-에틸-3-메톡시벤조일)-N′-(3-메틸벤조일)-N′-tert-부틸히드라진, N-(2-에틸-3-메톡시벤조일)-N′-(3,5-디클로로벤조일)-N′-tert-부틸히드라진, N-(2-에틸-3-메톡시벤조일)-N′-(2,4-디클로로벤조일)-N′-tert-부틸히드라진, N-(2-에틸-3-메톡시벤조일)-N′-(2-클로로-5-메틸벤조일)-N′-tert-부틸히드라진, N-(2-메틸-3,4-메틸렌디옥시벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(2-에틸-3,4-메틸렌디옥시벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(2-클로로-3,4-메틸렌디옥시벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(2-브로모-3,4-메틸렌디옥시벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(3-에톡시-2-에틸벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(3,4-(1,2-에틸렌디옥시)-2-메틸벤조일-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, 및 N-(2-에틸-3,4-(1,2-에틸렌디옥시)벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3,5-디메틸벤조일)-N′-네오펜틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3,5-디메틸벤조일)-N′-(메틸네오펜틸)히드라진, N-(2-에틸-3-메톡시벤조일)-N′-(3,5-디메틸벤조일)-N′-네오펜틸히드라진, 및 N-(2-에틸-3-메톡시벤조일)-N′-(3,5-디메틸벤조일)-N′-(메틸네오펜틸)히드라진으로부터 선택됨을 특징으로 하는 살충화합물.
  21. 식 N-(2-Ra-3-Rb-4-Rh-벤조일)-N′-(2-Rc-3-Rd-4-Re-5-Rf-벤조일-N′-Rg- 히드라진을 갖는 화합물을 하나 또는 이상 함유하는 살충조성물. 단, 상기 식에서 Ra는 할로 또는 저급 알킬; Rb는 저급 알콕시 또는 할로로 치환된 저급 알콕시; Rc는 수소, 브로모, 클로로, 플루오로, 저급 알킬, 저급알콕시, 저급알콕시저급알킬, 및 니트로로부터 선택하며; Rd,Re및 Rf는 수소, 브로모, 클로로, 플루오로, 저급알킬, 저급알콕시, 및 저급알콕시저급알킬로부터 각각 독립적으로 선택되며; Rg는 (C4-C6)알킬; Rh는 수소, 저급 알콕시, 저급 알킬, 또는 Rb와 함께 취할때는 옥시원자가 Rb자리에 위치한 메틸렌디옥시, 1,2-에틸렌디옥시 1,2-에틸렌옥시 또는 1,3-프로필렌옥시이며; 치환기 Rc와 Rd와 Re, 또는 Re, Rd, 또는 Rf를 함께 취할때는 메틸렌디옥시 또는 1,2-에틸렌디옥시일 수 있다.
  22. 제21항에 있어서, 나비목(order Lepidoptera)곤충을 제어하는데 사용됨을 특징으로 하는 살충 조성물.
  23. 제22항에 있어서, N-(3-메톡시-2-메틸벤조일)-N′-(3-클로로-5-메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3-메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3,5-디클로로벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3,4-디클로로벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3-메톡시-5-메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(4-플루오로벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3-메톡시-4-메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3,4-디메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-3(메톡시벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(4-클로로-3-메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(4-클로로-2-메톡시벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3-브로모-5-메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(4-클로로벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3-브로모-5-클로로벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3,5-디플루오로벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(4-메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3-클로로-4-플루오로벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3-플루오로벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3,4-디플루오로벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(2-메톡시-4-메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(2,4-디클로로벤조일)-N′-tert-부틸히드라진, N-(3-에톡시-2-메틸벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3-클로로벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-네오펜틸히드라진, N-(2-브로모-3-메톡시벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진,N-(2-클로로-3-메톡시벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(2-메틸-3-트리플루오로메톡시벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(4-메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3-브로모-4-플루오로벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3-플루오르-4-메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3-클로로-4-메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3-클로로-4-메톡시벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3,4,5-트리클로로벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3-에틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3,5-디클로로-4-플루오로벤조일)-N′-tert-부틸히드라진, N-(2-에틸-3-메톡시벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(2-에틸-3-메톡시벤조일)-N′-(3-클로로-5-메틸벤조일)-N′-tert-부틸히드라진, N-(2-에틸-3-메톡시벤조일)-N′-(3,5-디플루오로벤조일)-N′-tert-부틸히드라진, N-(2-에틸-3-메톡시벤조일)-N′-(3-메톡벤조일)-N′-tert-부틸히드라진, N-(2-에틸-3-메톡시벤조일)-N′-(3,5-메틸벤조일)-N′-tert-부틸히드라진, N-(2-에틸-3-메톡시벤조일)-N′-(3,5-디클로로벤조일)-N′-tert-부틸히드라진, N-(2-에틸-3-메톡시벤조일)-N′-(2,4-디클로로벤조일)-N′-tert-부틸히드라진, N-(2-에틸-3-메톡시벤조일)-N′-(2-클로로-5-메틸벤조일)-N′-tert-부틸히드라진, N-(2-클로로-3-메톡시벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(2-브로모-3-메톡시벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(3,4-메틸렌디옥시-2-메틸벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(2-에틸-3,4-메틸렌디옥시벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(2-클로로-3,4-메틸렌옥시벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(2-브로로-3,4-메틸렌디옥시벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(3,4-(1,2-에틸렌디옥시)-2-메틸벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, 및 N-(2-에틸-3,4-(1,2-에틸렌디옥시)벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, 및 -N′-tert-부틸히드라진으로부터 선택된 화합물을 하나 또는 그 이상 함유함을 특징으로 하는 살충조성물.
  24. 제23항에 있어서, N-(3-메톡시-2-메틸벤조일)-N′-(3-클로로-5-메틸벤조일)-N′-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(3-에톡시-2-메틸벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3-메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3,5-디클로로벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3,4-디클로로벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3-메톡시-5-메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(4-플루오로벤조일)-N′-tert-부틸히드라진, N-(2-클로로-3-메틸벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(3-브로모-3-메톡시벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(3,4-(1,2-에틸렌디옥시)-2-메틸벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, 및 N-(2-에틸-3,4-(1,2-에틸렌디옥시)벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진으로부터 선택된 화합물중 하나 또는 이상을 포함함을 특징으로 하는 살충 조성물.
  25. 제21항에 있어서, 동시목(order Homoptera) 해충을 제어하는데 사용됨을 특징으로 하는 살충 조성물.
  26. 제25항에 있어서, N-(2-에틸-3-메톡시벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(2-에틸-3-메톡시벤조일)-N′-(3-클로로-5-메틸벤조일)-N′-tert-부틸히드라진, N-(2-에틸-3-메톡시벤조일)-N′-(3-메톡시벤조일)-N′-tert-부틸히드라진, N-(2-에틸-3-메톡시벤조일)-N′-(2-메톡벤조일)-N′-tert-부틸히드라진, N-(2-에틸-3-메톡시벤조일)-N′-(2-클로로벤조일)-N′-tert-부틸히드라진, N-(2-에틸-3-메톡시벤조일)-N′-(3-메틸벤조일)-N′-tert-부틸히드라진, N-(3-에톡시-2-에틸벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(3,4-(1,2-에틸렌디옥시)-2-메틸벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, 및 N-(2-에틸-3,4-(1,2-에틸렌디옥시)벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진으로부터 선택된 화합물 중 하나 또는 그 이상을 포함함을 특징으로 하는 살충 조성물.
  27. 식 N-(2-Ra-3-Rb-4-Rh-벤조일)-N′-(2-Rc-3-Rd-4-Re-5-Rf-벤조일-N′-Rg- 히드라진을 갖는 화합물의 살충 유효양을 곤충과 접촉시키는 단계를 포함하는 해충 제어방법. 단, 상기 식에서 Ra는 할로 또는 저급 알킬; Rb는 저급 알콕시 또는 할로로 치환된 저급 알콕시; Rc는 수소, 브로모, 클로로, 플루오로, 저급알킬, 저급알콕시, 저급알콕시저급알킬, 및 니트로로부터 선택하며; Rd,Re및 Rf는 수소, 브로모, 클로로,플루오로, 저급알킬, 저급알콕시, 및 저급알콜시저급알킬로부터 각각 독립적으로 선택되며; Rg는 (C4-C6)알킬; Rh는 수소, 저급 알콕시, 저급 알킬이거나, Rb와 함께 취할때는 옥시원자가 Rb자리에 위치한 메틸렌디옥시, 1,2-에틸렌디옥시 1,2-에틸렌옥시 또는 1,3-프로필렌옥시이며; 치환기 Rc과 Rd또는 Rd와 Re, 또는 Re와 Rf를 함께 취할때는 메틸렌디옥시 또는 1,2-에틸렌디옥시일 수 있다.
  28. 27항에 있어서, 인시목(order Lepidoptera)곤충을 제어하는데 사용됨을 특징으로 하는 방법.
  29. 28항에 있어서, N-(3-메톡시-2-메틸벤조일)-N′-(3-클로로-5-메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-3(-메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3,5-디클로로벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3,4-디클로로벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3-메톡시-5-메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(4-플루오로벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3-메톡시-4-메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3,4-디메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3-메톡시벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(4-클로로-3-메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(4-클로로-2-메톡시벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3-브로모-5-메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(4-클로로벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3-브로모-5-클로로벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3,5-디플루오로벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(4-메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3-클로로-4-플루오로벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3-플루오로벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3,4-디플루오로벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(2-메톡시-4-메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(2,4-디클로로벤조일)-N′-tert-부틸히드라진, N-(3-에톡시-2-메틸벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3-클로로벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-네오펜틸히드라진, N-(2-브로모-3-메톡시벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(2-클로로-2-메톡시벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(2-메틸-3-트리플루오르메톡시벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(4-메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3-브로모-4-플루오로벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3-플루오로-4-메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3-클로로-4-메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3-클로로-4-메톡시벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3,4,5-트리클로로벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3-에틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3,5-디클로로-4-플루오로벤조일)-N′-tert-부틸히드라진, N-(2-에틸-3-메톡시벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(2-에틸-3-메톡시벤조일)-N′-(3-클로로-5-메틸벤조일)-N′-tert-부틸히드라진, N-(2-에틸-3-메톡시벤조일)-N′-(3,5-디플루로벤조일)-N′-tert-부틸히드라진, N-(2-에틸-3-메톡시벤조일)-N′-(3-메톡벤조일)-N′-tert-부틸히드라진, N-(2-에틸-3-메톡시벤조일)-N′-(3-메틸벤조일)-N′-tert-부틸히드라진, N-(2-에틸-3-메톡시벤조일)-N′-(3,5-디클로로벤조일)-N′-tert-부틸히드라진, N-(2-에틸-3-메톡시벤조일)-N′-(2,4-디클로로벤조일)-N′-tert-부틸히드라진, N-(2-에틸-3-메톡시벤조일)-N′-(2-클로로-5-메틸벤조일)-N′-tert-부틸히드라진, N-(2-클로로-3-메톡시벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(2-브로모-3-메톡시벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(3,4-에틸렌디옥시-2-메틸벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(2-에틸-3,4-메틸렌디옥시벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(2-클로로-3,4-메틸렌디옥시벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(2-브로모-3,4-메틸렌디옥시벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, 및 N-3,4-(1,2-에틸렌디옥시)-2-메틸벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, 및 N-(2-에틸-3,4-(1,2-에틸렌디옥시)벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진으로 부터 선택된 화합물중 하나 또는 그 이상을 함유함을 특징으로 하는 방법.
  30. 제29항에 있어서, N-(3-메톡시-2-메틸벤조일)-N′-(3-클로로-5-메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(3-에톡시-2-메틸벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3-메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3,5-디클로로벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3,5-디클로로벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(3-메톡시-5-메틸벤조일)-N′-tert-부틸히드라진, N-(3-메톡시-2-메틸벤조일)-N′-(4-플루오로벤조일)-N′-tert-부틸히드라진, N-(2-클로로-3-메틸벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(2-브로모-3-메톡시벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(3,4-(1,2-에틸렌디옥시)-2-메틸벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, 및 N-(2-에틸-3,4-(1,2-에틸렌디옥시)벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진으로부터 선택된 화합물중 하나 또는 이상을 포함함을 특징으로 하는 방법.
  31. 제27항에 있어서, 동시목(order Homoptera) 해충을 제어하는데 사용됨을 특징으로 하는 방법.
  32. 제31항에 있어서, N-(2-에틸-3-메톡시벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(2-에틸-3-메톡시벤조일)-N′-(3-클로로-5-메틸벤조일)-N′-tert-부틸히드라진, N-(2-에틸-3-메톡시벤조일)-N′-(3-메톡시벤조일)-N′-tert-부틸히드라진, N-(2-에틸-3-메톡시벤조일)-N′-(2-메톡벤조일)-N′-tert-부틸히드라진, N-(2-에틸-3-메톡시벤조일)-N′-(2-클로로벤조일)-N′-tert-부틸히드라진, N-(3-에톡시-2-에틸벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, N-(3-메틸-3-메톡시벤조일)-N′-(3-메틸벤조일)-N′-tert-부틸히드라진,-N′-(3,4-(1,2-에틸렌디옥시)-2-메틸벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진, 및 N-(2-에틸-3,4-(1,2-에틸렌디옥시)벤조일)-N′-(3,5-디메틸벤조일)-N′-tert-부틸히드라진으로부터 선택된 화합물중 하나 또는 그 이상을 포함함을 특징으로하는 살충 조성물.
  33. (1)3-아미노-2-(치환된)벤조산, (2)소디움 나이트리트, 및 (3)산성조건하의 알코올이나 알코올과 물의 혼합물을 효과적으로 혼합하는 단계를 포함하는 3-알콕시-2-(치환된)벤조산 제조공정.
  34. 제33항에 있어서, 상기 알코올을 메탄올임을 특징으로 하는 방법.
  35. (a)(i)3-아미노-2-(치환된)벤조산 또는 그 각각의 에스테르 및 (ii)산성조건하의 알코올 또는 알코올과 물의 혼합물,을 포함하는 조성물; (b)유효량의 무기산; 및 (c)소디움 나이트리트를, 혼합하는 단계를 포함하는 3-알콕시-2-(치환된)벤조산 또는 3-알콕시-2-(치환된)벤조산의 에스테르 제조공정.
  36. 제35항에 있어서, 상기 알코올은 메탄올 또는 에탄올임을 특징으로 하는 공정.
  37. 제36항에 있어서, 상기 알코올은 메탄올임을 특징으로 하는 3-메톡시-2-(치환된)벤조산 제조공정.
  38. 제37항에 있어서, 상기 3-메톡시-2-(치환된)벤조산은 3-메톡시-2-메틸벤조산임을 특징으로 하는 공정.
  39. 제37항에 있어서, 2-에틸-3-메톡시벤조산을 제조함을 특징으로 하는 공정.
  40. 제37항에 있어서, 상기 무기산은 브롬화 수소산, 염화수소산 염, 인산, 및 황산으로 부터 선택함을 특징으로 하는 공정.
  41. 제37항에 있어서, 약 0-100℃의 온도에서 행함을 특징으로하는 공정.
  42. 3,4-융합된 헤테로고리 벤조산 및 알킬 리튬 시약을 효과적으로 혼합한 후 후속적으로 친전자성 시약과 반응시키는 단계를 포함하는 2-알킬-3,4-융합된 헤테로고리 벤조산 또는 2-할로-3,4-융합된 헤테로고리 벤조산 제조공정.
  43. 제42항에 있어서, 2-알킬-3,4-융합된 헤테로고리 벤조산을 생성함을 특징으로 하는 공정.
  44. 제43항에 있어서, 상기 3,4-융합된 헤테로고리 벤조산은 3,4-메틸렌디옥시 벤조산, 3,4-(1,2-에틸렌디옥시)벤조산, 3,4-(1,3-프로필렌디옥시)벤조산, 3,4-(1,2-에틸렌옥시)벤조산, 또는 3,4-(1,3-프로필렌옥시)벤조산임을 특징으로 하는 공정.
  45. 제44항에 있어서, 상기 친전자성 시약은 메틸 요오드(methyl iodido) 또는 에틸 요오드(ethyl iodide)임을 특징으로 하는 방법.
  46. 제45항에 있어서, 2-메틸-3,4-메틸렌디옥시벤조산, 2-에틸-3,4-메틸렌디옥시벤조산, 2-메틸-3,4-(1,2-에틸렌디옥시)-2-메틸벤조산, 2-에틸-3,4-(1,2-에틸렌디옥시)벤조산, 2-메틸-3,4-(1,2-에틸렌옥시)벤조산, 2-에틸-3,4-(1,2-에틸렌디옥시)벤조산, 2-메틸-3,4-(1,3-프로필렌옥시)벤조산 또는 2-에틸-3,4-(1,3-프로필렌옥시)벤조산을 생성함을 특징으로 하는 방법.
  47. (a)(i)3,4-융함된 헤테로고리 벤조산과 (ii)비양성자성 용매를 함유하는 조성물, 및 (b)(i)알칼리듐 시약과 (ii)비양성자성 용매를 함유하는 조성물;을 약 -90~-20℃에서 약 1-4시간 동안 혼합한 후 (c)약 -90℃-실온에서 친전자성 시약을 후속적으로 혼합하는 단계를 포함하는 2-치환된-3,4-융합된 헤테로고리 벤조산 제조공정.
  48. 제47항에 있어서, 3,4-융합된 헤테로고리 벤조산은 3,4-메틸렌디옥시벤조 산, 3,4-(1,2-에틸렌디옥시)벤조산, 3,4-(1,3-프로필렌디옥시)벤조산, 3,4-(1,2-에틸렌옥시)벤조산, 또는 3,4-(1,3-프로필렌옥시)벤조산임을 특징으로 하는 공정.
  49. 제48항에 있어서, 비양성자성 반응용매는 테트라하이드로퓨란, 에틸 에테르, 1,4-디옥산, 헥산 또는 그것의 혼합물임을 특징으로 하는 공정.
  50. 제49항에 있어서, 용매는 테트라하이드로퓨란임을 특징으로 하는 공정.
  51. 제48항에 있어서, 알킬 리튬 시약은 n-부틸 리튬, sec-부틸 리튬, tert-부틸 리튬 또는 페닐 리튬임을 특징으로 하는 공정.
  52. 제51항에 있어서, 알킬 리튬 시약은 n-부틸 리튬임을 특징으로 하는 공정.
  53. 제48항에 있어서, 친전자성 시약은 화학식 R11Z로 나타내며, 상기 식에서 R11은 저급 알킬, 퍼할로알킬, 브로모, 클로로 또는 요오드이고 Z는 클로로, 브로모, 요오드, 알킬카르보닐, 알킬카르보닐옥시 또는 포밀임을 특징으로 하는 공정.
  54. 제53항에 있어서, 친전자성 시약은 메틸 요오드 또는 에틸 요오드 임을 특징으로 하는 공정.
  55. 제47항에 있어서, 2-메틸-3,4-메틸렌디옥시벤조산, 2-에틸-3,4-메틸렌디옥시벤조산, 2-메틸-3,4-(1,2-에틸렌디옥시)-2-메틸벤조산, 2-에틸-3,4-(1,2-에틸렌디옥시)벤조산, 2-메틸-3,4-(1,2-에틸렌옥시)벤조산, 2-에틸-3,4-(1,2-에틸렌옥시)벤조산, 2-메틸-3,4-(1,3-프로필렌옥시)벤조산 또는 2-에틸-3,4-(1,3-프로필렌옥시)벤조산을 생성함을 특징으로 하는 공정.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019930025020A 1992-11-23 1993-11-23 살충제로서유용한n'-치환된-n,n'-디아실히드라진류화합물및이를함유하는조성물과그들의사용방법 KR100317793B1 (ko)

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US07/984,189 US5344958A (en) 1992-11-23 1992-11-23 Insecticidal N'-substituted-N,N'-diacylhydrazines
US08/129,549 US5530028A (en) 1992-11-23 1993-09-29 Insecticidal N'-substituted-N,N'-diacylhydrazines
US129,549 1993-09-29

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Families Citing this family (61)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6013836A (en) * 1992-02-28 2000-01-11 Rohm And Haas Company Insecticidal N'-substituted-N,N'-disubstitutedhydrazines
US5369127A (en) * 1993-04-21 1994-11-29 Allergan, Inc. 1,3-benzodioxole and 1,2-dialkoxybenzene derivatives as ocular hypotensive agents
US5948406A (en) * 1996-08-12 1999-09-07 Rohm And Haas Company Immunogens, antibodies formed therefrom, and coating antigens useful in a diacylhydrazine immunoassay method
US5917079A (en) * 1996-09-24 1999-06-29 Rohm And Haas Company Process for synthesizing benzoic acids
DE19730848A1 (de) 1997-07-18 1999-01-21 Bayer Ag Verfahren zur Herstellung von 3-Hydroxy-2-methylbenzoesäure
US6013671A (en) * 1998-02-03 2000-01-11 Rohm And Haas Company Synergistic insecticidal compositions
US6124500A (en) * 1998-03-09 2000-09-26 Rohm And Haas Company Process for synthesizing benzoic acids
US6258603B1 (en) * 1998-06-17 2001-07-10 Rohm And Haas Company Ligands for modulating the expression of exogenous genes via an ecdysone receptor complex
DE19831710A1 (de) * 1998-07-15 2000-01-20 Merck Patent Gmbh Diacylhydrazinderivate
IL133121A (en) 1998-12-08 2004-06-20 Dow Agrosciences Llc Process for the preparation of benzoic acids-2-alkyl-3-hydroxy
US20040033600A1 (en) * 2001-03-21 2004-02-19 Palli Subba Reddy Ecdysone receptor-based inducible gene expression system
US8105825B2 (en) 2000-10-03 2012-01-31 Intrexon Corporation Multiple inducible gene regulation system
US6576422B1 (en) 2000-10-17 2003-06-10 Rohm And Haas Company Method for identifying products employing gene expression
WO2002066615A2 (en) * 2001-02-20 2002-08-29 Rheogene, Inc. Novel substitution mutant receptors and their use in a nuclear receptor-based inducible gene expression system
US8715959B2 (en) 2001-02-20 2014-05-06 Intrexon Corporation Substitution mutant receptors and their use in a nuclear receptor-based inducible gene expression system
ES2392508T3 (es) 2001-02-20 2012-12-11 Intrexon Corporation Receptores X retinoides quiméricos y su uso en un sistema inducible de expresión génica basado en receptores de ecdisona novedoso
MXPA03007493A (es) 2001-02-20 2004-10-15 Rheogene Holdings Inc Nuevo sistema de expresion genetica inducible a base de receptor de ecdisona/receptor x retinoide de invertebrado.
DE10244149A1 (de) * 2001-09-25 2003-04-30 Werner Keber Verfahren und Einrichtung zum Verhindern einer unzulässigen Flugannäherung von Flugzeugen an zu schützende Bodenobjeke
US7919269B2 (en) 2001-09-26 2011-04-05 Intrexon Corporation Whitefly ecdysone receptor nucleic acids, polypeptides, and uses thereof
MXPA04002810A (es) * 2001-09-26 2005-06-06 Rheogene Holdings Inc Acidos nucleicos receptores de ecdisona de saltarilla, polipeptidos, y sus usos.
US7375093B2 (en) 2002-07-05 2008-05-20 Intrexon Corporation Ketone ligands for modulating the expression of exogenous genes via an ecdysone receptor complex
US7304161B2 (en) * 2003-02-10 2007-12-04 Intrexon Corporation Diaclhydrazine ligands for modulating the expression of exogenous genes in mammalian systems via an ecdysone receptor complex
US7304162B2 (en) * 2003-02-21 2007-12-04 Intrexon Corporation Oxadiazoline ligands for modulating the expression of exogenous genes via an ecdysone receptor complex
US7456315B2 (en) 2003-02-28 2008-11-25 Intrexon Corporation Bioavailable diacylhydrazine ligands for modulating the expression of exogenous genes via an ecdysone receptor complex
US7935510B2 (en) 2004-04-30 2011-05-03 Intrexon Corporation Mutant receptors and their use in a nuclear receptor-based inducible gene expression system
US20070212716A1 (en) * 2006-02-10 2007-09-13 Commonwealth Scientific & Industrial Research Org. Nezara viridula Ecdysone Receptor
CA2689137C (en) 2007-05-29 2017-05-02 Intrexon Corporation Chiral diacylhydrazine ligands for modulating the expression of exogenous genes via an ecdysone receptor complex
JP2010536373A (ja) 2007-08-23 2010-12-02 イントレキソン コーポレーション 疾患を診断するための方法および組成物
BRPI0817009A2 (pt) * 2007-09-17 2014-10-07 Rohm & Haas Sistema de expressão de gene para a expressão controlável de resposta ao etileno em uma célula de planta, composição, e, métodos para produzir uma planta transgênica, e para modular sensibilidade ao etileno em uma planta.
CA2715080C (en) 2007-09-28 2021-09-28 Intrexon Corporation Therapeutic gene-switch constructs and bioreactors for the expression of biotherapeutic molecules, and uses thereof
CA2702058A1 (en) 2007-10-08 2009-04-16 Intrexon Corporation Engineered dendritic cells and uses for the treatment of cancer
WO2011119773A1 (en) 2010-03-23 2011-09-29 Roeth Jeremiah F Vectors conditionally expressing therapeutic proteins, host cells comprising the vectors, and uses thereof
CN103534355A (zh) 2011-03-04 2014-01-22 英特瑞克斯顿股份有限公司 条件性表达蛋白质的载体
MX369690B (es) 2011-09-08 2019-11-19 Intrexon Corp Diacilhidrazina cristalina y sus usos.
CN103563953A (zh) * 2012-08-05 2014-02-12 南京华洲药业有限公司 一种含甲氧虫酰肼和氟啶脲的复合杀虫组合物及其用途
CN102863355B (zh) * 2012-09-24 2014-05-21 浙江禾田化工有限公司 一种n-(3-甲氧基-2-甲基苯甲酰基)-n’-叔丁基肼的提纯方法
CN102960356A (zh) * 2012-12-12 2013-03-13 海利尔药业集团股份有限公司 一种含有双三氟虫脲与甲氧虫酰肼的杀虫组合物
CN103416409A (zh) * 2012-12-15 2013-12-04 海利尔药业集团股份有限公司 一种含有氟螨嗪与甲氧虫酰肼的杀虫组合物
AU2014227571B2 (en) 2013-03-15 2017-02-02 Intrexon Corporation Boron-containing diacylhydrazines
CN103222466A (zh) * 2013-04-26 2013-07-31 南通金陵农化有限公司 一种吡蚜酮和甲氧虫酰肼的复配农药
CN104072383A (zh) * 2014-07-10 2014-10-01 四川北方红光特种化工有限公司 制备3-氨基-2-甲基苯甲酸的方法
EP3194359B1 (en) 2014-09-17 2020-04-08 Intrexon Corporation Boron-containing diacylhydrazine compounds
US10721933B2 (en) 2015-01-23 2020-07-28 Syngenta Participations Ag Pesticidally active semi-carbazones and thiosemicarbazones derivatives
EP3347373A1 (en) 2015-10-10 2018-07-18 Intrexon Corporation Improved therapeutic control of proteolytically sensitive, destabilized forms of interleukin-12
MX2018005886A (es) 2015-11-11 2018-08-15 Intrexon Corp Composiciones y metodos para la expresion de polipeptidos biologicamente activos a partir de un vector unico para tratamiento de condiciones cardiacas y otras patologias.
UY37343A (es) 2016-07-25 2018-02-28 Intrexon Corp Control del fenotipo en plantas
WO2018089527A1 (en) 2016-11-09 2018-05-17 Intrexon Corporation Frataxin expression constructs
AU2018207281B2 (en) 2017-01-10 2024-08-01 Precigen, Inc. Modulating expression of polypeptides via new gene switch expression systems
CN108530297B (zh) * 2017-03-03 2021-09-24 联化科技股份有限公司 2-氯-3-甲基苯甲酸及其中间体的制备方法
CN109384667A (zh) * 2017-08-02 2019-02-26 江苏永安化工有限公司 一种2-甲基-3-甲氧基苯甲酰氯的合成工艺
KR20200128703A (ko) 2018-03-06 2020-11-16 프레시전 인코포레이티드 B형 간염 백신 및 이의 용도
CN109776464A (zh) * 2019-03-26 2019-05-21 江苏省农药研究所股份有限公司 呋喃虫酰肼的制备方法、中间体及其制备方法
WO2020206056A1 (en) 2019-04-04 2020-10-08 Greenvenus Llc Peptides and methods of plant protection
CN113121339B (zh) * 2021-04-19 2022-10-11 江苏永安化工有限公司 一种3-羟基-2-甲基苯甲酸甲酯与3-甲氧基-2-甲基苯甲酸甲酯的联产工艺
CN113511968A (zh) * 2021-04-19 2021-10-19 江苏永安化工有限公司 一种2-甲基-3-甲氧基苯甲酸的合成工艺
US20240268386A1 (en) 2021-05-14 2024-08-15 Syngenta Crop Protection Ag Seed treatment compositions
WO2022268813A1 (en) 2021-06-24 2022-12-29 Syngenta Crop Protection Ag Insect, acarina and nematode pest control
WO2022268815A1 (en) 2021-06-24 2022-12-29 Syngenta Crop Protection Ag Insect, acarina and nematode pest control
GB2612942A (en) * 2021-09-16 2023-05-24 Rotam Agrochem Int Co Ltd A crystalline form of methoxyfenozide, a process for its preparation and use of the same
WO2023105064A1 (en) 2021-12-10 2023-06-15 Syngenta Crop Protection Ag Insect, acarina and nematode pest control
CN117654560B (zh) * 2023-12-01 2024-06-04 安徽泽升科技股份有限公司 一种通过氧化氨基连续化制备硝基化合物的方法

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4161611A (en) * 1976-02-23 1979-07-17 Veesicol Chemical Corporation Process for the production of 2-methoxy-3,6-dichlorobenzoic acid
US4389401A (en) * 1979-07-10 1983-06-21 Rohm And Haas Company Arthropod repellents
US5117057A (en) * 1985-10-21 1992-05-26 Rohm And Haas Company Insecticidal N' substituted-N-N'-disubstituted-hydrazines
DK483586A (da) * 1985-10-21 1987-04-22 Rohm & Haas Insecticide n'-substituerede-n,n'-diacylhydraziner
US4985461A (en) * 1985-10-21 1991-01-15 Rohm And Haas Company Insecticidal N'-substituted-N,N'-diacylhydrazines
US5110986A (en) * 1988-04-26 1992-05-05 Rohm And Haas Company Synthesis of n-t-alkyl-1,2-diacylhydrazines
JPH0660142B2 (ja) * 1989-06-02 1994-08-10 田辺製薬株式会社 ビフェニル誘導体、その製法及びその合成中間体
AU637573B2 (en) * 1988-06-16 1993-06-03 Dow Agrosciences Llc Hydrazine derivatives for pharmaceutical use
US4954655A (en) * 1989-03-31 1990-09-04 Rohm And Haas Company Preparation of alkylhydrazines
NZ228936A (en) * 1989-05-01 1992-04-28 Rohm & Haas Method for treating insect infestation in rice plants comprising applying diacylhydrazine derivatives
JPH0539252A (ja) * 1990-08-01 1993-02-19 Nippon Kayaku Co Ltd Ｎ，Ｎ’−ジベンゾイル−ｔｅｒｔ−ブチルヒドラジン誘導体およびそれを有効成分とする殺虫組成物
JP3068846B2 (ja) * 1990-08-01 2000-07-24 日本化薬株式会社 新規ヒドラジン誘導体およびそれを有効成分とする殺虫組成物
US5110979A (en) * 1991-01-15 1992-05-05 Imperial Chemical Industries Plc Trisubstituted benzoic acid intermediates
IL100643A (en) * 1991-01-25 1996-10-31 Nippon Kayaku Kk History of hydrazine and pesticides containing these histories as an active ingredient
US5334753A (en) * 1992-03-12 1994-08-02 Rhone-Poulenc Agriculture Ltd Processes for preparing ortho-substituted benzoic acids

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