KR890701567A - 헤테로사이클릭 화합물 - Google Patents

헤테로사이클릭 화합물

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KR890701567A
KR890701567A KR1019890700897A KR890700897A KR890701567A KR 890701567 A KR890701567 A KR 890701567A KR 1019890700897 A KR1019890700897 A KR 1019890700897A KR 890700897 A KR890700897 A KR 890700897A KR 890701567 A KR890701567 A KR 890701567A
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alkyl
chloro
methyl
dioxo
dihydro
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벵거 쟝
빈터니쯔 파울
젤러 마틴
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쟝-쟈크 오가이, 프리돌린 클라우스너
에프.호프만-라 로슈 앤드 캄파니 아크티엔 게젤샤프트
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Publication of KR890701567A publication Critical patent/KR890701567A/ko

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    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
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    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
    • C07C259/10—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to carbon atoms of six-membered aromatic rings
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
    • C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/08—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing alicyclic rings
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    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/08—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing alicyclic rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
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  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

내용 없음

Description

헤테로사이클릭 화합물
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (16)

  1. 하기 일반식(Ⅰ)의 화합물과 하기 일반식(Ⅰ)에서 R1이 C1-4-알킬, C3-또는 C4-알켄일 또는 C3-또는 C4알킨일을 나타내고, R6이 수소, 할로겐 또는 C1-4-알킨올 나타내며, R7이 C1-4-할로알킬을 나타내는 일반식(Ⅰ)의 화합물의 상응하는 엔올 에테르 및 R1및 /또는 R2가 수소를 나타내는 일반식(Ⅰ)의 화합물 또는 엔올 에테르의 염.
    상기식에서, R1C1-4-알킬, C1-4-할로알킬, C3- 또는 C4-알킬 또는 C3-또는 C4-알킨일을 나타내고, R2및 R3은 각각 독립적으로 수소, C1-8-알킬, C2-8-알켄일, C3-8-알킨일, C1-8-할로알킬, C1-8-하이드록시알킬, C1-4-알콕시-C1-8-알킬, C1-4-알킬티오-C1-8-알킬,C1-4-할로알콕시-C1-8-알킬, C2-8-시아노알킬, C1-8-니트로알킬, C2-9-카복시알킬, C2-5-알콕시카보닐-C1-8-알킬, C1-4-알킬설포닐-C1-8-알킬, 디(C1-4-알킬)-포스포노-C1-8-알킬, C3-8-사이클로알킬, C1-8-알콕시 또는 임의로 할로겐, 하이드록시, C1-4-알킬, C1-4-할로알킬, C1-4-알콕시, C1-4-알킬티오, C1-4-할로알콕시, 시아노, 니트로 카복시 및/ 또는 C2-5-알콕시카보닐에 의해 치환된 페닐 또는 페닐-C1-4-알킬(이에 의해 임의로 치환되는 페닐은 융합, 포화카보사이클릭 5 내지 7원 환 또는 1 또는 2개의 산소원자를 함유하는 5내지 7원의 융합, 포화 헤테로사이클릭 환을 가질수 있다)을 나타내며, 이때 R2및 R3은 모두 C1-8-알콕시일 수 없거나, R2및 R3은 이들이 결합된 질소 원자와 함께 임의로, C1-6-알킬에 의해 일치환 또는 다치환되고 또한 질소원자 이외에 산소원자, 황원자 및/또는 다른 질소원자가 환에 존재할수 있는 4내지 7원 헤테로사이클릭 환을 나타내고, R4는 할로겐 또는 시아노를 나타내고, R5는 수소 또는 할로겐을 나타내고, R6은 수소, 할로겐 또는 C1-4-알킬을 나타내고, R7은 C1-4-알킬이거나, R1이 C1-4-할로알킬이 아닌 경우, C1-4-할로알킬을 나타내거나, R6및 R7은 함께 트리-또는 테트라메틸렌을 나타낸다.
  2. 제1항에 있어서, R1이 C1-4-알킬 또는 C1-4-플루오로알킬을 나타내는 화합물.
  3. 제1항 또는 제2항에 있어서, R2가 수소 또는 C1-8-알킬을 나타내고, R3이 C1-8-알킬, C2-8-알켄일, C3-8-알킨일, C2-8-시아노알킬 또는 C3-8사이클로알킬을 나타내는 화합물.
  4. 제1항 또는 제2항에 있어서, R2가 수소 또는 C1-8-알킬을 나타내고, R3이 벤질을 나타내는 화합물.
  5. 제1항 내지 제4항중 어느 한 항에 있어서, R4가 염소 또는 브롬을 나타내고, R5가 수소 또는 불소를 나타내는 화합물.
  6. 제1항 내지 제5항중 어느 한 항에 있어서 R6이 수소, 불소 또는 메틸을 나타내고, R7이 C1-4-할로알킬을 나타내는 화합물.
  7. 제1항 내지 제5항중 어느 한 항에 있어서 R6이 수소, 불소 또는 메틸을 나타내고, R7이 C1-4-알킬을 나타내는 화합물.
  8. 제1항에 있어서, N-에틸-2-클로로-5-[3,6-디하이드로-2,6-디옥소-3-메틸-4-트리플루오로메틸-1(2H)-피리디딘일]-4-플루오로벤즈아미드, N-프로필-2-클로로-5-[3,6-디하이드로-2,6-디옥소-3-메틸-4-트리플루오로메틸-1(2H)-피리디딘일]-4-플루오로벤즈아미드, N-이소프로필-2-클로로-5-[3,6-디하이드로-2,6-디옥소-3-메틸-4-트리플루오로메틸-1(2H)-피리미딘일]-4-플루오로벤즈아미드,N-부틸-2-클로로-5-[3,6-디하이드로-2,6-디옥소-3-메틸-4-트리플루오로메틸-1(2H)-피리디딘일]-4-플루오로벤즈아미드, N-(S-부틸)-2-클로로-5-[3,6-디하이드로-2,6-디옥소-3-메틸-4-트리플루오로메틸-1(2H)-피리디딘일]-4-플루오로벤즈아미드, N-알릴-2-클로로-5-[3,6-디하이드로-2,6-디옥소-3-메틸-4-트리플루오로메틸-1(2H)-피리디딘일]-4-플루오로벤즈아미드, N-(2-메틸-2-프로펜일)-2-클로로-5-[3,6-디하이드로-2,6-디옥소-3-메틸-4-트리플루오로메틸-1(2H)-피리디딘일]-4-플루오로벤즈아미드, N-프로파프길-2-클로로-5-[3,6-디하이드로-2,6-디옥소-3-메틸-4-트리플루오로메틸-1(2H)-피리디딘일]-4-플루오로벤즈아미드, N-(1,1,-디메틸-2-프로핀일)-2-클로로-5-[3,6-디하이드로-2,6-디옥소-3-메틸-4-트리플루오로메틸-1(2H)-피리디딘일]-4-플루오로벤즈아미드, N-(1-시아노-메틸에틸)-2-클로로-5-[3,6-디하이드로-2,6-디옥소-3-메틸-4-트리플루오로메틸-1(2H)-피리디딘일]-4-플루오로벤즈아미드, N-(1-시아노-1,2-디메틸프로필)-2-클로로-5-[3,6-디하이드로-2,6-디옥소-3-메틸-4-트리플루오로메틸-1(2H)-피리미딘일]-4-플루오로벤즈아미드, N-사이클로프로필-2-클로로-5-[3,6-디하이드로-2,6-디옥소-3-메틸-4-트리플루오로메틸-1(2H)-피리디딘일]-4-플루오로벤즈아미드, N-사이클로헥실-2-클로로-5-[3,6-디하이드로-2,6-디옥소-3-메틸-4-트리플루오로메틸-1(2H)-피리미딘일]-4-플루오로벤즈아미드, N-벤질-2-클로로-5-[3,6-디하이드로-2,6-디옥소-3-메틸-4-트리플루오로메틸-1(2H)-피리디딘일]-4-플루오로벤즈아미드, N-(1-페닐미딘일)-2-클로로-5-[3,6-디하이드로-2,6-디옥소-3-메틸-4-트리플루오로메틸-1(2H)-피리디딘일]-4-플루오로벤즈아미드, N,N-디에틸-2-클로로-5-[3,6-디하이드로-2,6-디옥소-3-메틸-4-트리플루오로메틸-1(2H)-피리미딘일]-4-플루오로벤즈아미드, N-알릴-2-클로로-5-[3,6-디하이드로-3,4-디메틸-2,6-디옥소-1(2H)-피리미딘일]-4-플루오로벤즈아미드, N-(1-시아노-메틸에틸)-2-클로로-5-[3,6-디하이드로-3,4-디메틸-2,6-디옥소-1(2H)-피리미딘일]-4-플루오로벤즈아미드, N-알릴-2-클로로-5-[3,6-디하이드로-2,6-디옥소-3-메틸-4-펜타플루오로메틸-1(2H)-피리미딘일]-4-플루오로벤즈아미드, 및 N-알릴-2-클로로-5-[3,6-디하이드로-3,4-디메틸-2,6-디옥소-1(2H)-피리미딘일]-벤즈아미드로부터 선택되는 화합물.
  9. 제1항에 있어서, N-알릴-2-클로로-5-[3-디플루오로메틸-3,6-디하이드로-2,6-디옥소-4-메틸-1(2H)-피리미딘일]-플루오로벤즈아미드인 화합물.
  10. 하기 일반식(ⅩⅤ)의 화합물.
    상기식에서, R2및 R3은 각각 독립적으로 수소, C1-8-알킬, C3-8-알켄일, C3-8알킨일, C1-8할로알킬, C1-8-하이드록시알킬, C1-4-알콕시-C1-8-알킬,C1-4-알킬티오-C1-8-알킬, C1-4-할로알콕시-C1-8-알킬, C2-8-시아노알킬,C1-8-니트로알킬, C2-9-카복시알킬, C2-5-알콕시카보닐-C1-8-알킬, C1-4-알킬설포닐-C1-8-알킬, 디(C1-4-알킬)-포스포노-C1-8-알킬, C2-8-사이크로알킬, C1-8-알콕시 또는 임의로 할로겐, 하이드록시, C1-4-알킬, C1-4-할로알킬, C1-4-알콕시, C1-4-알킬티오, C1-4-할로알콕시, 시아노, 니트로, 카복시 및/또는 C2-5-알콕시카보닐에 의해 치환된 페닐 또는 페닐-C1-4-알킬(이에 의해 임의로 치환되는 페닐은 융합, 포화카보사이크릭 5 내지 7원 환 또는 1또는 2개의 산소원자를 함유하는 5내지 7원의 융합, 포화 헤테로사이클릭 환을 가질수 있다)을 나타내며, 이때 R2및 R3은 모두 C1-8-알콕시일 수 없거나, R2및 R3은 이들의 결합된 질소원자와 함께 임의로 C1-6-알킬에 의해 일치환 또는 다치환되고 또한 질소원자 이외에 산소원자, 황원자 및/또는 다른 질소원자가 환에 존재할수 있는 4내지 7원 헤테로사이클릭 환을 나타내고, R4는 할로겐 또는 시아노를 나타내고, R5는 수소 또는 할로겐을 나타내고, R12는 니트로, 아미노, 이소이소시아네이토, (C1-6-알콕시)-카보닐아미노 또는 우레이도를 나타내며, R12이 니트로 또는 아미노를 나타내는 경우, R5는 불소만을 나타낸다.
  11. 적어도 하나의 일반식(Ⅰ)의 화합물 또는 일반식(Ⅰ)에서 R1이 C1-4-알킬, C3-또는 C4-알켄일 또는 C3-또는 C4-알킨일을 나타내고, R5이 수소, 할로겐 또는 C1-4-알킬을 나타내고, R7이 C1-4-할로알킬을 나타내는 일반식(Ⅰ)의 화합물의 엔을 에테르 또는 R1및/또는 R2가 수소를 나타내는 일반식(Ⅰ)의 화합물 또는이의 엔을 에테르 염의 유효량 및 제형 보조제를 함유함을 특징으로 하는 잡초 방제 조성물.
    상기식에서, R1은 수소, C1-8-알킬, C2-8-알켄일, C3-8-알킨일, C1-8-할로알킬,C1-8-하이드록시알킬, C1-4-알콕시-C1-8-알킬, C1-4-알킬티오-C1-8-알킬, C1-4-할로알콕시-C1-8-알킬,C2-8-시아노알킬, C1-8-니트로알킬, C2-9-카복시알킬, C2-5-알콕시카보닐-C1-8-알킬, C1-4-알킬설포닐-C1-8-알킬, 디(C1-4-알킬)-포스포노-C1-8-알킬, C3-8-사이클로알킬, C1-8-알콕시 또는 임의로 할로겐, 하이드록시, C1-4-알킬, C1-4-할로알킬, C1-4-알콕시, C1-4-알킬티오, C1-4-할로알콕시, 시아노, 니트로, 카복시 및/ 또는 C2-5-알콕시카보닐에 의해 치환된 페닐 또는 페닐-C1-4-알킬(이에 의해 임의로 치환된 페닐은 융합, 포화카보사이클릭 5 내지 7원환 또는 1또는 2개의 산소원자를 함유하는 5내지 7원의 융합, 포화 헤테로사이클릭 환을 가질수 있다)을 나타내며, 이때 R2및 R3은 모두 C1-8-알콕시일수 없거나, R2및 R3은 이들이 결합된 질소원자와 함께 임의로 C1-6-알킬에 의해 일치환 또는 다치환 되고 또한 질소원자 이외에 산소원자, 황원자 및/또는 다른 질소원자가 환에 존재할수 있는 4내지 7원 헤테로사 이클릭 환을 나타내고, R4는 할로겐 또는 시아노를 나타내고, R5는 수소 또는 할로겐을 나타내고, R6은 수소, 할로겐 또는 C1-4-알킬을 나타내고, R7은 C1-4-알킬이거나, R1이 C1-4-할로알킬이 아닌 경우, C1-4-할로알킬을 나타내거나, R6및 R7은 함께 트리-또는 테트라메틸렌을 나타낸다.
  12. 제11항에 있어서, 하기의 그룹으로부터 선택되어도 적어도 하나의 화합물 유효량과 재형 보조제를 함유함을 특징으로 하는 잡초 방제 조성물. N-에틸-2-클로로-5-[3,6-디하이드로-2,6-디옥소-3-메틸-4-트리플루오로메틸-1(2H)-피리미딘일]-4-플루오로벤즈아미드, N-프로필-2-클로로-5-[3,6-디하이드로-2,6-디옥소-3-메틸-4-트리플루오로메틸-1(2H)-피리미딘일]-4-플루오로벤즈아미드, N-이소프로필-2-클로로-5-[3,6-디하이드로-2,6-디옥소-3-메틸-4-트리플루오로메틸-1(2H)-피리미딘일]-4-플루오로벤즈아미드, N-부틸-2-클로로-5-[3,6-디하이드로-2,6-디옥소-3-메틸-4-트리플루오로메틸-1(2H)-피리미딘일]-4-플루오로벤즈아미드, N-(S-부틸)-2-클로로-5-[3,6-디하이드로-2,6-디옥소-3-메틸-4-트리플루오로메틸-1(2H)-피리미딘일]-4-플루오로벤즈아미드, N-알릴-2-클로로-5-[3,6-디하이드로-2,6-디옥소-3-메틸-4-트리플루오로메틸-1(2H)-피리미딘일]-4-플루오로벤즈아미드, N-(2-메틸-2-프로펜일)-2-클로로-5-[3,6-디하이드로-2,6-디옥소-3-메틸-4-트리플루오로메틸-1(2H)-피리미딘일]-4-플루오로벤즈아미드, N-프로파르길-2-클로로-5-[3,6-디하이드로-2,6-디옥소-3-메틸-4-트리플루오로메틸-1(2H)-피리미딘일]-4-플루오로벤즈아미드, N-(1,1-디메틸-2-프로핀일)-2-클로로-5-[3,6-디하이드로-2,6-디옥소-3-메틸-4-트리플루오로메틸-1(2H)-피리미딘일]-4-플루오로벤즈아미드, N-(1-시아노-메틸에틸)-2-클로로-5-[3,6-디하이드로-2,6-디옥소-3-메틸-4-트리플루오로메틸-1(2H)-피리미딘일]-4-플루오로벤즈아미드, N-(1-시아노-1,2-디메틸프로필)-2-클로로-5-[3,6-디하이드로-2,6-디옥소-3-메틸-4-트리플루오로메틸-1(2H)-피리미딘일]-4-플루오로벤즈아미드, N-사이클로프로필-2-클로로-5-[3,6-디하이드로-2,6-디옥소-3-메틸-4-트리플루오로메틸-1(2H)-피리미딘일]-4-플루오로벤즈아미드, N-사이클로헥실-2-클로로-5-[3,6-디하이드로-2,6-디옥소-3-메틸-4-트리플루오로메틸-1(2H)-피리미딘일]-4-플루오로벤즈아미드, N-벤질-2-클로로-5-[3,6-디하이드로-2,6-디옥소-3-메틸-4-트리플루오로메틸-1(2H)-피리미딘일]-4-플루오로벤즈아미드, N-(1-페닐에틸)-2-클로로-5-[3,6-디하이드로-2,6-디옥소-3-메틸-4-트리플루오로메틸-1(2H)-피리미딘일]-4-플루오로벤즈아미드, N,N-디에틸-2-클로로-5-[3,6-디하이드로-2,6-디옥소-3-메틸-4-트리플루오로메틸-1(2H)-피리미딘일]-4-플루오로벤즈아미드,N-알릴-2-클로로-5-[3,6-디하이드로-3,4-디메틸-2,6-디옥소-1(2H)-피리미딘일]-4-플루오로벤즈아미드, N-(1-시아노-메틸에틸)-2-클로로-5-[3,6-디하이드로-3,4-디메틸-2,6-디옥소-1(2H)-피리미딘일]-4-플루오로벤즈아미드, N-알릴-2-클로로-5-[3,6-디하이드로-2,6-디옥소-3-메틸-4-펜타플루오로메틸-1(2H)-피리미딘일]-4-플루오로벤즈아미드, 및 N-알릴-2-클로로-5-[3,6-디하이드로-3,4-디메틸-2,6-디옥소-1(2H)-피리미딘일]-4-벤즈아미드.
  13. 제11항에 있어서, 유효량의 N-알릴-2-클로로-5-[3-디플루오로메틸-3,6-디하이드로-2,6-디옥소-4-메틸-1(2H)-피리미딘일]-4-플루오로벤즈아미드와 제형 보조제를 함유함을 특징으로 하는 잡초 방제 조성물.
  14. a)일반식(Ⅱ)의 또는 일반식(Ⅲ)의 화합물을 양성자기 이탈된 형태의 또는 일반식(Ⅴ)의 화합물과 반응시켜 R1이 수소를 나타내는 일반식(Ⅰ)의 화합물을 제조하거나, b)일반식(Ⅴ)의 화합물을 일반식(Ⅵ)또는 일반식(Ⅶ)의 화합물과 반응시켜 R1이 수소를 나타내는 일반식(Ⅰ)의 화합물을 제조하거나, c) 일반식(Ⅰ')의 화합물을 알킬화시켜 R1이 C1-4-알킬, C1-4-할로알킬, C4-알켄일, C3-또는C-4-알킨일을 나타내는 일반식(Ⅰ)의 화합물을 제조하거나, d) 일반식 (Ⅷ)의 화합물을 양성자가 이탈된 형태의 일반식(R1'OH)(여기서, R1'는 C1-4-알킬, C3- 또는 C4-알켄일 또는 C3-또는 C4-알킨일을 나타낸다)의 알킨올, 알켄올 또는 알킨올로 처리하여 R2및 R3이 수소가 아닌 일반식(Ⅰ)화합물이 엔을 에테르를 제조하거나, e)반응성 유도체의 형태로 존재할 수 있는 일반식(Ⅸ)의 벤조산 또는 일반식(Ⅸa)의 각각의 엔을 에테로를 일반식(Ⅹ)의 아민과 반응시켜 R1이 C1-4-알킬, C1-4-할로알킬, C3-는 C4-알켄일 또는 C3-또는 C4-알킨일인 일반식(Ⅰ) 화합물이 및 R1이 C1-4-알킬, C3-또는 C4-알켄일 또는 C3또는 C4-알킨일-나타내고, R6이 수소, 할로겐 또는 C1-4-알킬을 나타내고, R7이 C1-4-할로알킬을 나타내는 일반식(Ⅰ)의 화합물의 엔을 에테로를 제조하고, 경우에 따라 이렇게 하여 수득한 R1및/또는 R2가 수소를 나타내는 일반식(Ⅰ) 화합물 또는 이이렇게 하여 수득한 R2가 수소를 나타내는 엔올 에테르를 염으로 전환시킴을 특징으로 하여, 일반식(Ⅰ)의 화합물과 일반식(Ⅰ)에서 R1이 C1-4-알킬, C3-또는 C4-알켄일 또는 C3-또는 C4-알킨일을 나타내고, R6이 수소, 할로겐 또는 C1-4-알킬을 나타내고, R7이 C1-4-할로알킬을 나타내는 일반식(Ⅰ)의 화합물에 상응하는 엔올 에테르 및 R1및 / 또는 R2가 수소를 나타내는 일반식(Ⅰ)의 화합물 및 엔올 에테르의 염을 제조하는 방법.
    상기식에서, R1은 수소, C1-8-알킬, C2-8-알켄일, C3-8-알킨일, C1-8-할로알킬, C1-8-하이드록시알킬, C1-4-알콕시-C1-8-알킬, C1-4-알킬티오-C1-8-알킬, C1-4-할로알콕시-C1-8-알킬, C2-8-시아노알킬, C1-8-니트로알킬, C2-9-카복시알킬, C2-5-알콕시카보닐--C1-8-알킬, -C1-4-알킬설포닐-C1-8-알킬,디(C1-4-알킬)-포스포노-C1-8-알킬, C3-8-사이클로알킬, C1-8-알콕시 또는 임의로 할로겐, 하이드록시, C1-4-알킬, C1-4-할로알킬, C1-4-알콕시, C1-4-알킬티오, C1-4-할로알콕시, 시아노, 니트로, 카복시 및/ 또는 C2-5-알콕시카보닐에 의해 치환된 페닐 또는 페닐-C1-4-알킬(이에 의해 임의로 치환되는 페닐은 융합, 포화카보사이클릭 5내지 7원 환 또는 1또는 2개의 산소원자를 함유하는 5내지 7원의 융합, 포화 헤테로사이클릭 환을 가질수 있다)을 나타내며, 이때 R2및 R3은 모두 C1-8-알콕시일수 없거나, R2및 R3은 이들이 결합된 질소 원자와 함께 임의로 C1-8-알킬에 의해 일치환 또는 다치환되고 또한 질소이외에 산소원자, 황원자 및/또는 다른 질소원자가 환에 존재할수 있는 4내지 7원 헤테로사이클릭 환을 나타내고, R4는 할로겐 또는 시아노를 나타내고, R5는 수소 또는 할로겐을 나타내고, R6은 수소, 할로겐 또는 C1-4-알킬을나타내고,R7은 C1-4알킬이거나,R1이 C1-4-할로알킬이 아닌 경우, C1-4-할로알킬을 나타내거나, R6및 R7은 함께 트리- 또는 테트라메틸렌을 나타내고, R1'는 상기에서 정의한 바와 같고, R1"는 C1-4-알킬, C1-4-할로알킬, C3-또는 C4-알켄일 또는 C3-또는 C-4알킨일을 나타내고, R2' 및 R3'는 수소를 제외하고는 상기한 R2와 R3에 대한 의미를 갖고, R6'는 수소, 할로겐 또는 C1-4-알킬을 나타내고, R7'는 C1-4-할로알킬을 나타내고, Hal 은 염소 또는 브롬을 의미하고, R8, R9및 R10은 저급 알킬을 나타낸다.
  15. 제1항 내지 제9항에 있어서, 어느 한항에 있어서, 화합물 또는 제11항에 내지 제13항 중의 어느 한 항에 따르는 조성물 유효량을 잡초에 대해 보호해야할 장소및/또는 잡초에 처리함을 특징으로 하는 잡초를 방제하는 방법.
  16. 잡초를 방제하기 위한, 제1항에 내지 제9항중의 어느 한항에 따르는 화합물 또는 제11항 내지 제13항중의 어느 한항에 따르는 조성물의 용도.
    ※ 참고사항: 최초출원 내용에 의하여 공개하는 것임.
KR1019890700897A 1987-09-23 1988-09-19 헤테로사이클릭 화합물 KR890701567A (ko)

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WO1989002891A1 (en) 1989-04-06
US5017211A (en) 1991-05-21
AU2328188A (en) 1989-04-18
HU203542B (en) 1991-08-28

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