KR920016422A - N-페닐카바메이트 화합물, 이의 제조방법 및 유해한 유기체를 방제하기 위한 살균 조성물 - Google Patents

N-페닐카바메이트 화합물, 이의 제조방법 및 유해한 유기체를 방제하기 위한 살균 조성물 Download PDF

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KR920016422A
KR920016422A KR1019920001806A KR920001806A KR920016422A KR 920016422 A KR920016422 A KR 920016422A KR 1019920001806 A KR1019920001806 A KR 1019920001806A KR 920001806 A KR920001806 A KR 920001806A KR 920016422 A KR920016422 A KR 920016422A
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South Korea
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hydrogen atom
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KR1019920001806A
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데루마사 고묘지
이타루 시게하라
노리후사 마쓰오
히로시 시모하라다
다케시 오시마
도시오 아카기
시게루 미타니
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아키자와 아키라
이시하라산교 가부시키가이샤
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Publication of KR920016422A publication Critical patent/KR920016422A/ko

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    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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Abstract

내용 없음

Description

N-페닐카바메이트 화합물, 이의 제조방법 및 유해한 유기체를 방지하기 위한 살균조성물
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Claims (17)

  1. 하기 일반식(I)의 N-페닐카바메이트 화합물 또는 이의 염.
    상기식에서, R1은 비치환되거나 치환된 알킬그룹이고;R2는 수소원자, 비치환되거나 치환된 알킬 그룹, 비치환되거나 치환된 알케닐 그룹, 비치환되거나 치환된 사이클로알킬 그룹이거나 또는 -COX1그룹(여기서,X1는 비치환되거나 치환된 알킬그룹, 비치환되거나 치환된 알케닐 그룹,비치환되거나 치환된 알키닐 그룹, 비치환되거나 치환된 사이클로알킬 그룹, 또는 비치환되거나 치환된 알콕시 그룹이다)이며; Z는 -CH2S-그룹, -SCH2-그룹,-CO2O-그룹, -OCH2-그룹, -CH2-CH2-그룹, -CH=CH-그룹, -C≡C-그룹, -CH2SO-그룹,-CH2SO2-그룹, -CH2SCH2-그룹,-CH2O-N=C(R4)-그룹이고, 이들 각각의 우측 실선은 R3에 대한 결합을 나타내며;R3는 비치환되거나 치환된 페닐그룹,비치환되거나 치환된 피리딜 그룹, 비치환되거나 치환된 벤조티아졸릴 그룹, 비치환되거나 치환된 벤즈옥사졸릴 그룹,비치환되거나 치환된 벤즈이미다졸릴 그룹,비치환되거나 치환된 이미다조피리딜 그룹, 비치환되거나 치환된 나프틸 그룹, 비치환되거나 치환된 피리미디닐 그룹, 비치환되거나 치환된 티에닐 그룹, 비치환되거나 치환된 푸릴 그룹, 비치환되거나 치환된 티아졸리닐 그룹, 비치환되거나 치환된 옥사졸리닐 그룹, 비치환되거나 치환된 푸릴 그룹, 비치환되거나 치환된 티아졸릴 그룹, 비치환되거나 치환된 이미다졸 비치환되거나 치환된 옥사졸릴 그룹, 비치환되거나 치환된 피라졸릴 그룹, 비치환되거나 치환된 퀴놀릴 그룹, 비치환되거나 치환된 인돌릴 그룹, 비치환되거나 치환된 피롤릴 그룹, 비치환되거나 치환된 디하이드로벤조푸릴 그룹,비치환되거나 치환된 벤조티에닐 그룹, 비치환되거나 치환된 인다닐 그룹, 비치환되거나 치환된 테트라하이드로나프틸 그룹, 비치환되거나 치환된 벤조푸릴 그룹, 비치환되거나 치환된 디하이드로 벤조티에닐 그룹, 비치환되거나 치환된 벤즈옥사지닐 그룹, 비치환되거나 치환된 벤조티아지닐 그룹, 비치환되거나 치환된 벤조일 그룹이고 ;R4는 수소 원자, 비치환되거나 치환된 알킬그룹, 비치환되거나 치환된 사이클로알킬 그룹, 비치환되거나 치환된 알콕시그룹, 비치환되거나 치환된 알킬티오 그룹, 비치환되거나 치환된 페닐그룹, 시아노그룹, -NR5R6그룹, 또는 -CO2R7그룹,이며; R5및 R6는 각기 독립적으로 수소원자 또는 비치환되거나 치환된 알킬 그룹이거나 이들이 결하된 질소원자와 함께 5-내지 7- 원 헤테로사이클릭 그룹을 형성하고; R7은 비치환되거나 치환된 알킬그룹이며;A는 수소원자, 할로겐 원자, 비치환되거나 치환된 알킬그룹, 비치환되거나 치환된 알콕시 그룹, 비치환되거나 치환된 페녹시 그룹, 또는 비치환되거나 치환된 피리딜옥시 그룹이고; 단, (1)Z가 -CH2SO-그룹 또는 -CH2SO2-그룹인 경우R2는 수소원자이고, (2)(ⅰ)R1이 메틸그룹이고, R2가 수소원자이며-Z-R3그룹이 2-니트로-3-피리딜옥시메틸 그룹, 페닐에틸닐 그룹, 스티릴 그룹 도는 2-브로모벤질옥시 그룹인 경우와, (ⅱ)R1이 에틸그룹이고, R2가 수소원자이고-Z-R3가 벤질옥시 그룹, 페닐에티닐 그룹, 스티릴 그룹 또는 2-브로모벤질티오 그룹인 경우는 제외된다.
  2. 제1항에 있어서, Z가 -CH2O-N=C(R4)-그룹이고, R4가 수소원자, 비치환되거나 치환된 알킬 그룹, 비치환되거나 치환된 알콕시 그룹, 또는 비치환되거나 치환된 알킬티오 그룹인 N-페닐카바메이느 화합물 또는 이의 염.
  3. 제1항에 있어서, R2가 수소원자, 비치화되거나 알킬그룹, 비치환되거나 치환된 알키닐 그룹, 또는 -COX1그룹(여기서, X1은 비치환되거나 치환된 알킬 그룹이다)인 N-페닐카바메이트 화합물 또는 이의 염.
  4. 제1항에 있어서, R3이 비치환되거나 치환된 페닐그룹, 비치환되거나 치환된 피리딜 그룹, 비치환되거나 치환된 티에닐 그룹, 비치환되거나 치환된 푸릴그룹, 비치환되거나 치환된 인다닐 그룹 똔느 비치환되거나 치환된 디하이드로벤조 푸릴 그룹인 N-페닐카바메이트 화합물 또는 이의 염.
  5. 제1항에 있어서, R2가 비치환되거나 치환된 알킬 그룹이고,Z가 -CH2O--N=C(R4)-그룹이며, R3이 비치환되거나 치환된 페닐 그룹, 비치환되거나 치환된 피리딜 그룹, 비치환되거나 치환된 티에닐 그룹, 비치환되거나 치환된 푸릴그룹, 비치환되거나 치환된 인다닐 그룹, 또는 비치환되거나 치환된 디하이드로벤조푸릴 그룹이고R4가 비치환되거나 치환된 알킬 그룹이 N-페닐카바메트 화합물 또는 이의 염.
  6. 제5항에 있어서, R2가 메틸그룹, 에틸 그룹 또는 메톡시메틸 그룹이고, R4가 메틸인 그룹인 N-페닐카바메이트 화합물 또는 이의 염.
  7. 제6항에 있어서, 메틸 N-(메톡시메틸)-N-[2[(-메틸벤질리덴)아미노 옥시메틸]페닐]카바메이트, 메틸 N-(에틸)-N-[2-[(-메틸벤질리덴)아미노옥시메틸]페닐]카바메이트, 메틸 N-(메톡시페닐)-N-[2-〔〔α메틸-3,4-(메틸렌 디옥시)벤질리덴〕아미노옥시메틸〕페닐〕카바메이트, 메틸 N-(에틸)-N-〔2-〔〔α-메틸-3,4-메틸렌 디옥시)벤질리덴 ]아미노옥시메틸]페닐]카바메이트, 메틸 N-(메톡시메틸)-N-[2-[〔-메틸-4-이소프로독시]벤질리덴〕아미노옥시메틸]페닐]카바메이트, 메틸 N-(메톡시메틸)-N-[2-[〔-메틸-4-이소프로폭시)벤질리덴)아미노옥시메틸]페닐]카바메이트, 메틸 N-(메톡시메틸)-N-[2-[〔-메틸-4-(에톡시)-3-(메톡시)벤질리덴]아미노옥시메틸]페닐]카바메이트, 메틸 N-(메톡시메틸)-N-[2-[〔-메틸-4(메톡시)-3-(메틸벤질리덴)〕아미노옥시메틸]페닐]카바메이트, 메틸 N-(메톡시메틸)-N[1-[(2,3-디하이드로-5-벤조푸릴)에틸리덴)아미노옥시메틸]페닐]카바메이트, 메틸 N-(메톡시메틸)-N-[2-[〔1-(5-인다닐)에틸리덴〕아미노옥시메틸]페닐]카바메이트, 메틸 N-(메톡시메틸)-N-〔2-〔〔1-(5-트리플루오로메틸-2-피리딜)에틸리덴〕아미노옥시메틸〕페닐〕카바메이트 또는 메틸 N-(메톡시메틸)-N-[2-[〔1-(5-클로로-2-피리딜)에틸리덴)아미노옥시메틸]페닐]카바메이트인 N-페닐카바메이트 화합물 또는 이의 염.
  8. 제1항에 있어서, Z가 -CH=CH-그룹인 N-페닐 카바메이트 화합물 또는 이의 염.
  9. 제8항에 있어서, R2가 수소원자 또는 비치환 되거나 치환된 알킬그룹이고, Z가 -CH-CH-그룹이며, R3,가 비치환 되거나 치환된 페닐 그룹인 N-페닐카바메이트 화합물.
  10. 제9항에 있어서, R2가 수소원자, 메틸 그룹, 에틸 그룹 또는 메톡시메틸 그룹인 N-페닐카바메이트 화합물.
  11. 제10항에 있어서, 메틸N-(메톡시메틸 )-N[2-(2-클로로스티릴)페닐]카바메이트인 -N-페닐카바메이트 화합물.
  12. 활성 성분으로서 하기 일반식(I)의 N-페닐카바메이트 화합물 또는 이의 염을 포함하는, 유해한 미생물을 방지하기 위한 살균 조성물.
    상기식에서, R1은 비치환되거나 치환된 알킬그룹이고;R2는 수소원자, 비치환되거나 치환된 알킬 그룹, 비치환되거나 치환된 알케닐 그룹, 비치환되거나 치환된 알키는 그룹비치환되거나 치환된 사이클로알킬 그룹이거나 또는 -COX1그룹(여기서,X1는 비치환되거나 치환된 알킬그룹, 비치환되거나 치환된 알케닐 그룹,비치환되거나 치환된 알키닐 그룹, 비치환되거나 치환된 사이클로알킬 그룹, 또는 비치환되거나 치환된 알콕시 그룹이다)이며; Z는 -CH2S-그룹, -SCH2-그룹,-CO2O-그룹, -OCH2-그룹, -CH2-CH2-그룹, -CHCH-그룹, -CC-그룹, -CH2SO-그룹,-CH2SO2-그룹, -CH2SCH2-그룹,-CH2O-N=C(R4)-그룹이고, 이들 각각의 우측 실선은 R3에 대한 결합을 나타내며;R3는 비치환되거나 치환된 페닐그룹,비치환되거나 치환된 피리딜 그룹, 비치환되거나 치환된 벤조티아졸릴 그룹, 비치환되거나 치환된 벤즈옥사졸릴 그룹,비치환되거나 치환된 벤즈이미다졸릴 그룹,비치환되거나 치환된 이미다조피리딜 그룹, 비치환되거나 치환된 나프틸 그룹, 비치환되거나 치환된 피리미디닐 그룹, 비치환되거나 치환된 티에닐 그룹, 비치환되거나 치환된 푸릴 그룹, 비치환되거나 치환된 티아졸리닐 그룹, 비치환되거나 치환된 옥사졸리닐 그룹, 비치환되거나 치환된 피라지닐 그룹, 비치환되거나 치환된 티아졸릴 그룹, 비치환되거나 치환된 옥사졸릴 그룹, 비치환되고나 치환된 이미다졸릴 그룹, 비치환되거나 치환된 피라졸릴 그룹, 비치환되거나 치환된 퀴놀릴 그룹, 비치환되거나 치환된 인돌릴 그룹, 비치환되거나 치환된 피롤릴 그룹, 비치환되거나 치환된 벤조푸릴 그룹,비치환되거나 치환된 벤조티에닐 그룹, 비치환되거나 치환된 인다닐 그룹, 비치환되거나 치환된 테트라하이드로나프틸 그룹, 비치환되거나 치환된 벤조푸릴 그룹, 비치환되거나 치환된 디하이드로 벤조티에닐 그룹, 비치환되거나 치환된 벤즈옥사지닐 그룹, 비치환되거나 치환된 벤조티아지닐 그룹, 비치환되거나 치환된 벤조일 그룹이고 ;R4는 수소 원자, 비치환되거나 치환된 알킬그룹, 비치환되거나 치환된 사이클로알킬 그룹, 비치환되거나 치환된 알콕시그룹, 비치환되거나 치환된 알킬티오 그룹, 비치환되거나 치환된 페닐그룹, 시아노그룹, -NR5R6그룹, 또는 -CO2R7그룹,이며; R5및 R6는 각기 독립적으로 수소원자 또는 비치환되거나 치환된 알킬 그룹이거나 이들이 결하된 질소원자와 함께 5-내지 7- 원 헤테로사이클릭 그룹을 형성하고; R7은 비치환되거나 치환된 알킬그룹이며;A는 수소원자, 할로겐 원자, 비치환되거나 치환된 알킬그룹, 비치환되거나 치환된 알콕시 그룹, 비치환되거나 치환된 페녹시 그룹, 또는 비치환되거나 치환된 피리딜옥시 그룹이고; 단, (1)Z가 -CH2SO-그룹 또는 -CH2SO2-그룹인 경우R2는 수소원자이고, (2)(ⅰ)R1이 메틸그룹이고, R2가 수소원자이며-Z-R3그룹이 2-니트로-3-피리딜옥시메틸 그룹, 페닐에틸닐 그룹, 스티릴 그룹 도는 2-브로모벤질옥시 그룹인 경우와, (ⅱ)R1이 에틸그룹이고, R2가 수소원자이고-Z-R3가 벤질옥시 그룹, 페닐에티닐 그룹, 스티릴 그룹 또는 2-브로모벤질티오 그룹인 경우는 제외된다.
  13. 하기 일반식 (Ⅱ)의 화합물 또는 이의 염을 일반식(Ⅴ)의 화합물과 반응시킴을 특징으로 하여, 일반식(I-I)으 N-페닐카바메이트 화합물, 또는 이의 염을 제조하는 방법.
    상기식에서, R1은 비치환되거나 치환된 알킬그룹이고;R2는 수소원자, 비치환되거나 치환된 알킬 그룹, 비치환되거나 치환된 알케닐 그룹, 비치환되거나 치환된 알키닐그룹, 비치환되거나 치환된 사이클로알킬 그룹이거나 또는 -COX1그룹(여기서,X1는 비치환되거나 치환된 알킬그룹, 비치환되거나 치환된 알케닐 그룹,비치환되거나 치환된 알키닐 그룹, 비치환되거나 치환된 사이클로알킬 그룹, 또는 비치환되거나 치환된 알콕시 그룹이다)이며; Z는 -CH2S-그룹, -SCH2-그룹,-CO2O-그룹, -OCH2-그룹, -CH2-CH2-그룹, -CH=CH-그룹, -C≡C-그룹, -CH2SCH2-그룹, 또는 -CH2O-N=C(R4)-그룹이고, 이들 각각의 우측 실선은 R3에 대한 결합을 나타내며;R3는 비치환되거나 치환된 페닐그룹,비치환되거나 치환된 피리딜 그룹, 비치환되거나 치환된 벤조티아졸릴 그룹, 비치환되거나 치환된 벤즈옥사졸릴 그룹,비치환되거나 치환된 벤즈이미다졸릴 그룹,비치환되거나 치환된 이미다조피리딜 그룹, 비치환되거나 치환된 나프틸 그룹, 비치환되거나 치환된 피리미디닐 그룹, 비치환되거나 치환된 티에닐 그룹, 비치환되거나 치환된 푸릴 그룹, 비치환되거나 치환된 티아졸리닐 그룹, 비치환되건카 치환된 옥사졸리닐 그룹, 비치환되거나 치환된 피라지닐 그룹, 비치환되거나 치환된 티아졸릴 그룹, 비치환되거나 치환된 옥사졸릴 그룹, 비치환되거나 치환된 이미다졸릴 그룹, 비치환되거나 치환된 피라졸릴 그룹, 비치환되거나 치환된 퀴놀릴 그룹, 비치환되거나 치환된 인돌릴 그룹, 비치환되거나 치환된 피롤릴 그룹, 비치환되거나 치환된 벤조푸릴 그룹,비치환되거나 치환된 벤조티에닐 그룹, 비치환되거나 치환된 인다닐 그룹, 비치환되거나 치환된 테트라하이드로나프틸 그룹, 비치환되거나 치환된 디하이드로 벤조푸릴 그룹, 비치환되거나 치환된 디하이드로 벤조티에닐 그룹, 비치환되거나 치환된 벤즈옥사지닐 그룹, 비치환되거나 치환된 벤조티아지닐 그룹, 비치환되거나 치환된 벤조일 그룹이고 ;R4는 수소 원자, 비치환되거나 치환된 알킬그룹, 비치환되거나 치환된 사이클로알킬 그룹, 비치환되거나 치환된 알콕시그룹, 비치환되거나 치환된 알킬티오 그룹, 비치환되거나 치환된 페닐그룹, 시아노그룹, -NR5R6그룹, 또는 -CO2R7그룹,이며; R5및 R6는 각기 독립적으로 수소원자 또는 비치환되거나 치환된 알킬 그룹이거나 이들이 결하된 질소원자와 함께 5-내지 7- 원 헤테로사이클릭 그룹을 형성하고; R7은 비치환되거나 치환된 알킬그룹이며;A는 수소원자, 할로겐 원자, 비치환되거나 치환된 알킬그룹, 비치환되거나 치환된 알콕시 그룹, 비치환되거나 치환된 페녹시 그룹, 또는 비치환되거나 치환된 피리딜옥시 그룹이고; 단, (ⅰ)R1이 메틸그룹이고, R2가 수소원자이며-Z′-R3그룹이 2-니트로-3-피리딜옥시메틸 그룹, 페닐에틸닐 그룹, 스티릴 그룹 도는 2-브로모벤질옥시 그룹인 경우와, (ⅱ)R1이 에틸그룹이고, R2가 수소원자이고-Z′-R3가 벤질옥시 글부, 페닐에티닐 그룹, 스티릴 그룹 또는 2-브로모벤질티오 그룹인 경우는 제외된다.
  14. 하기 일반식 (Ⅲ)의 화합물을 일반식(Ⅵ)의 화합물과 반응시킴을 특징으로 하여, 일반식(I-2)의 N-페닐카바메이트 화합물, 또는 이의 염을 제조하는 방법.
    상기식에서, R1은 비치환되거나 치환된 알킬그룹이고;Z′-CH2S-그룹, -SCH2-그룹,-CO2O-그룹, -OCH2-그룹, -CH2-CH2-그룹, -CH=CH-그룹, -C≡C-그룹, -CH2SCH2-그룹,-CH2O-N=C(R4)-그룹이고, 이들 각각의 우측 실선은 R3에 대한 결합을 나타내며;R3는 비치환되거나 치환된 페닐그룹,비치환되거나 치환된 피리딜 그룹, 비치환되거나 치환된 벤조티아졸릴 그룹, 비치환되거나 치환된 벤즈옥사졸릴 그룹,비치환되거나 치환된 벤즈이미다졸릴 그룹,비치환되거나 치환된 이미다조피리딜 그룹, 비치환되거나 치환된 나프틸 그룹, 비치환되거나 치환된 피리미디닐 그룹, 비치환되거나 치환된 티에닐 그룹, 비치환되거나 치환된 푸릴 그룹, 비치환되거나 치환된 티아졸리닐 그룹, 비치환되거나 치환된 옥사졸리닐 그룹, 비치환되거나 치환된 피라지닐 그룹, 비치환되거나 치환된 티아졸릴 그룹, 비치환되거나 치환된 옥사졸릴 그룹, 비치환되거나 치환된 이미다졸릴 그룹, 비치환되거나 치환된 피라졸릴 그룹, 비치환되거나 치환된 퀴놀릴 그룹, 비치환되거나 치환된 인돌릴 그룹, 비치환되거나 치환된 피롤릴 그룹, 비치환되거나 치환된 벤조푸릴 그룹,비치환되거나 치환된 벤조티에닐 그룹, 비치환되거나 치환된 인다닐 그룹, 비치환되거나 치환된 테트라하이드로나프틸 그룹, 비치환되거나 치환된 디하이드로 벤조푸릴 그룹, 비치환되거나 치환된 디하이드로 벤조티에닐 그룹, 비치환되거나 치환된 벤즈옥사지닐 그룹, 비치환되거나 치환된 벤조티아지닐 그룹, 비치환되거나 치환된 벤조일 그룹이고 ;R4는 수소 원자, 비치환되거나 치환된 알킬그룹, 비치환되거나 치환된 사이클로알킬 그룹, 비치환되거나 치환된 알콕시그룹, 비치환되거나 치환된 알킬티오 그룹, 비치환되거나 치환된 페닐그룹, 시아노그룹, -NR5R6그룹, 또는 -CO2R7그룹,이며; R5및 R6는 각기 독립적으로 수소원자 또는 비치환되거나 치환된 알킬 그룹이거나 이들이 결하된 질소원자와 함께 5-내지 7- 원 헤테로사이클릭 그룹을 형성하고; R7은 비치환되거나 치환된 알킬그룹이며;A는 수소원자, 할로겐 원자, 비치환되거나 치환된 알킬그룹, 비치환되거나 치환된 알콕시 그룹, 비치환되거나 치환된 페녹시 그룹, 또는 비치환되거나 치환된 피리딜옥시 그룹이고; 단, (1)Z가 -CH2SO-그룹 또는 -CH2SO2-그룹인 경우R2는 수소원자이고, (2)(ⅰ)R1이 메틸그룹이고, R2가 수소원자이며-Z-R3그룹이 2-니트로-3-피리딜옥시메틸 그룹, 페닐에틸닐 그룹, 스티릴 그룹 도는 2-브로모벤질옥시 그룹인 경우와, (ⅱ)R1이 에틸그룹이고, R2가 수소원자이고-Z′-R3가 벤질옥시 글부, 페닐에티닐 그룹, 스티릴 그룹 또는 2-브로모벤질티오 그룹인 경우는 제외된다.
  15. 하기 일반식 (I-2)의 화합물 또는 이의 염을 일반식(Ⅶ)의 화합물과 반응시킴을 특징으로 하여, 일반식(I-3)의 N-페닐카바메이트 화합물, 또는 이의 염을 제조하는 방법.
    상기식에서, R1은 비치환되거나 치환된 알킬그룹이고;Y 비치환되거나 치환된 알킬 그룹, 비치환되거나 치환된 알케닐 그룹, 비치환되거나 치환된 알키닐 그룹, 비치환되거나 치환된 사이클로알킬 그룹이거나 또는 -COX1그룹(여기서,X1는 비치환되거나 치환된 알킬그룹, 비치환되거나 치환된 알케닐 그룹,비치환되거나 치환된 알키닐 그룹, 비치환되거나 치환된 사이클로알킬 그룹, 또는 비치환되거나 치환된 알콕시 그룹이다)이며; Z′는 -CH2S-그룹, -SCH2-그룹,-CO2O-그룹, -OCH2-그룹, -CH2-CH2-그룹, -CH=CH-그룹, -C≡C-그룹, -CH2SCH2-그룹,-CH2O-N=C(R4)-그룹이고, 이들 각각의 우측 실선은 R3에 대한 결합을 나타내며;R3는 비치환되거나 치환된 페닐그룹,비치환되거나 치환된 피리딜 그룹, 비치환되거나 치환된 벤조티아졸릴 그룹, 비치환되거나 치환된 벤즈옥사졸릴 그룹,비치환되거나 치환된 벤즈이미다졸릴 그룹,비치환되거나 치환된 이미다조피리딜 그룹, 비치환되거나 치환된 나프틸 그룹, 비치환되거나 치환된 피리미디닐 그룹, 비치환되거나 치환된 티에닐 그룹, 비치환되거나 치환된 푸릴 그룹, 비치환되거나 치환된 티아졸리닐 그룹,비치환되거나 치환된 옥사졸리닐 그룹, 비치환되거나 치환된 피라지닐 그룹, 비치환되거나 치환된 티아졸릴 그룹, 비치환되거나 치환된 옥사졸릴 그룹, 비치환되거나 치환된 피라졸릴 그룹, 비치환되거나 치환된 퀴놀릴 그룹, 비치환되거나 치환된 인돌릴 그룹, 비치환되거나 치환된 피롤릴 그룹, 비치환되거나 치환된 벤조푸릴 그룹,비치환되거나 치환된 벤조티에닐 그룹, 비치환되거나 치환된 인다닐 그룹, 비치환되거나 치환된 테트라하이드로나프틸 그룹, 디하이드로 비치환되거나 치환된 벤조푸릴 그룹, 비치환되거나 치환된 디하이드로 벤조티에닐 그룹, 비치환되거나 치환된 벤즈옥사지닐 그룹, 비치환되거나 치환된 벤조티아지닐 그룹, 비치환되거나 치환된 벤조일 그룹이고 ;R4는 수소 원자, 비치환되거나 치환된 알킬그룹, 비치환되거나 치환된 사이클로알킬 그룹, 비치환되거나 치환된 알콕시그룹, 비치환되거나 치환된 알킬티오 그룹, 비치환되거나 치환된 페닐그룹, 시아노그룹, -NR5R6그룹, 또는 -CO2R7그룹,이며; R5및 R6는 각기 독립적으로 수소원자 또는 비치환되거나 치환된 알킬 그룹이거나 이들이 결합된 질소원자와 함께 5-내지 7- 원 헤테로사이클릭 그룹을 형성하고; R7은 비치환되거나 치환된 알킬그룹이며;A는 수소원자, 할로겐 원자, 비치환되거나 치환된 알킬그룹, 비치환되거나 치환된 알콕시 그룹, 비치환되거나 치환된 페녹시 그룹, 또는 비치환되거나 치환된 피리딜옥시 그룹이고;W는 염소원자, 브롬원자 또는 요오드 원자이다.
  16. 하기 일반식 (I-4)의 화합물 또는 이의 염을 산화제와 반응시킴을 특징으로 하여, 일반식(I-5)의 N-페닐카바메이트 화합물, 또는 이의 염을 제조하는 방법.
    상기식에서, R1은 비치환되거나 치환된 알킬그룹이고;R3는 비치환되거나 치환된 페닐그룹, 비치환되거나 치환된 피리딜 그룹, 비치환되거나 치환된 벤조티아졸릴 그룹, 비치환되거나 치환된 벤즈옥사졸릴 그룹,비치환되거나 치환된 벤즈이미다졸릴 그룹,비치환되거나 치환된 이미다조피리딜 그룹, 비치환되거나 치환된 나프틸 그룹, 비치환되거나 치환된 피리미디닐 그룹, 비치환되거나 치환된 티에닐 그룹, 비치환되거나 치환된 푸릴 그룹, 비치환되거나 치환된 티아졸리닐 그룹, 비치환되거나 치환된 옥사졸릴 그룹, 비치환되거나 치환된 피라지닐 그룹, 비치환되거나 치환된 티아졸릴 그룹, 비치환되거나 치환된 옥사졸릴 그룹, 비치환되거나 치환된 이미다졸릴 그룹, 비치환되거나 치환된 피라졸릴 그룹,비치환되거나 치환된 퀴놀릴 그룹, 비치환되거나 치환된 인돌릴 그룹, 비치환되거나 치환된 피롤릴 그룹, 비치환되거나 치환된 벤조푸릴 그룹, 비치환되거나 치환된 디하이드로 벤조티에닐 그룹, 비치환되거나 치환된 인다닐 그룹, 비치환되거나 치환된 테트라하이드로나프틸 그룹,비치환되거나 치환된 다이하드로 벤조푸릴 그룹, 비치환되거나 치환된 다이하르로벤조티에닐 그룹, 비치환되거나 치환된 벤즈옥사지닐 그룹, 비치환되거나 치환된 벤조티아지닐 그룹,비치환되거나 치환된 벤조일 그룹이며 ;A는 수소 원자, 할로겐 원자, 비치환되거나 치환된 알킬 그룹, 비치환되거나 치환된 알콕시그룹, 비치환되거나 치환된 페녹시 그룹, 비치환되거나 치환된 피리딜옥시 그룹이고 ;n은 1또는 2 이다.
  17. 하기 일반식 (Ⅵ)의 화합물을 일반식(Ⅷ)의 화합물과 반응시킴을 특징으로 하여 일반식(I-6)의 N-페닐카바메이트 화합물, 또는 이의 염을 제조하는 방법.
    상기식에서, R1은 비치환되거나 치환된 알킬그룹이고;R3비치환되거나 치환된 페닐 그룹, 비치환되거나 치환된 피리딜 그룹, 비치환되거나 치환된 벤조티아졸 그룹, 비치환되거나 치환된 벤즈옥사졸릴 그룹, 치환된 벤즈이미다졸릴 그룹, 비치환되거나 치환된 이미다조피리딜 그룹, 비치환되거나 치환된 나프틸 그룹, 비치환되거나 치환된 피리미디닐 그룹, 비치환되거나 치환된 티에닐 그룹, 비치환되거나 치환된 푸릴 그룹, 비치환되거나 치환된 티아졸리닐 그룹, 비치환되거나 치환된 옥사졸리닐 그룹, 비치환되거나 치환된 피라지닐 그룹, 비치환되거나 치환된 티아졸릴 그룹, 비치환되거나 치환된 옥사졸릴 그룹, 비치환되거나 치환된 이미다졸릴 그룹, 비치환되거나 치환된 피라졸릴 그룹, 비치환되거나 치환된 퀴놀릴 그룹, 비치환되거나 치환된 인돌릴 그룹, 비치환되거나 치환된 피롤릴 그룹, 비치환되거나 치환된 벤조푸릴 그룹, 비치환되거나 치환된 벤조티에닐 그룹, 비치환되거나 치환된 디하이드로 벤조푸릴 그룹, 비치환되거나 치환된 벤조티에닐 그룹, 비치환되거나 치환된 인다닐 그룹, 비치환되거나 치환된 테트라하이드로나프틸 그룹, 비치환되거나 치환된 다이하드로벤조푸릴 그룹, 또는 비치환되거나 치환된 벤즈옥사지닐 그룹, 비치환되거나 치환된 벤조티아지닐 그룹, 비치환되거나 치환된 벤조일 그룹이고,;Q는 산소원자, 황원자,-SCH2-그룹 또는 -O-N=C(R4)-그룹이며 각각의 우측실선은 R3로 향하는 결합을 나타내고;R4는 수소 원자, 비치환되거나 치환된 알킬그룹, 비치환되거나 치환된 사이클로알킬 그룹, 비치환되거나 치환된 알콕시 그룹, 비치환되거나치환된 알킬티오 그룹, 비치환되거나 치환된 페닐 그룹, 시아노그룹, -NR5R6그룹, 또는 -CO2R7그룹,이며; R5및 R6는 각기 독립적으로 수소원자 또는 비치환되거나 치환된 알킬 그룹이거나 이들이 결합된 질소원자와 함께 5-내지 7- 원 헤테로사이클릭 그룹을 형성하고; R7은 비치환되거나 치환된 알킬그룹이며;A는 수소원자, 할로겐 원자, 비치환되거나 치환된 알킬그룹, 비치환되거나 치환된 알콕시 그룹, 비치환되거나 치환된 페녹시 그룹, 또는 비치환되거나 치환된 피리딜옥시 그룹이고;W는 염소원자,브롬원자 또는 요오드원자이며;단 (i)R1이 메틸 그룹이고,-Q-R3가 2-니트로 -3-피리딜옥시 그룹인 경우는 제외된다,
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
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SI9210092B (en) 2001-02-28
AU640852B2 (en) 1993-09-02
HUT60241A (en) 1992-08-28
IL100807A0 (en) 1992-09-06
DE69220820D1 (de) 1997-08-21
MY110439A (en) 1998-05-30
AU1075992A (en) 1992-08-13
DE69220820T2 (de) 1997-12-11
TR28289A (tr) 1996-04-24
ES2106792T3 (es) 1997-11-16
PH30945A (en) 1997-12-23
EP0498396A2 (en) 1992-08-12
CA2060623A1 (en) 1992-08-08
SI9210092A (sl) 1998-06-30
CN1065659A (zh) 1992-10-28
JPH05170726A (ja) 1993-07-09
CS34192A3 (en) 1992-09-16
NZ241526A (en) 1993-10-26
ATE155459T1 (de) 1997-08-15
PL169429B1 (pl) 1996-07-31
EP0498396A3 (en) 1993-02-24
DK0498396T3 (da) 1998-02-23
IL100807A (en) 1997-03-18
GR3024473T3 (en) 1997-11-28
UY23372A1 (es) 1992-03-15
MX9200538A (es) 1992-08-01
YU9292A (sh) 1994-09-09
RU2049775C1 (ru) 1995-12-10
CZ284332B6 (cs) 1998-10-14
US5436267A (en) 1995-07-25
HRP921200B1 (en) 2000-06-30
BR9200398A (pt) 1992-10-13
EP0498396B1 (en) 1997-07-16
HRP921200A2 (en) 1997-04-30
PL293413A1 (en) 1993-03-22
RO107939B1 (ro) 1994-01-31
HU9200370D0 (en) 1992-05-28

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