KR970064375A - Novel pyrrol-2-one derivatives for the control of plant pathogens and their preparation - Google Patents

Novel pyrrol-2-one derivatives for the control of plant pathogens and their preparation Download PDF

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KR970064375A
KR970064375A KR1019960007613A KR19960007613A KR970064375A KR 970064375 A KR970064375 A KR 970064375A KR 1019960007613 A KR1019960007613 A KR 1019960007613A KR 19960007613 A KR19960007613 A KR 19960007613A KR 970064375 A KR970064375 A KR 970064375A
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alkyl
halogen
general formula
following general
substituted
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KR0156680B1 (en
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류요섭
김성기
유성훈
전재훈
김문정
편승엽
최우봉
전성욱
전삼재
이성백
박현철
조진호
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성재갑
주식회사 Lg 화학
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—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
    • C07D207/30—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
    • C07D207/34—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/38—2-Pyrrolones

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

Abstract

본 발명은 하기 일반식(Ⅰ)으로 표시되는 식물병원균 퇴치용 피롤-2-온 유도체 및 그의 제조방법에 관한 것이다.The present invention relates to a pyrrol-2-one derivative represented by the following general formula (I) for eliminating plant pathogens and a process for producing the same.

상기 식에서 X는 l 내지 3개 존재할 수 있고, 각각 독립적으로 C1-C3알킬 또는 할로겐원자를 나타내고, R1은 할로겐, C1-C2알킬티오, 메톡시, 또는 할로겐, C1-C3알킬, 니트로에 의해 치환되거나 비치환된 페닐을 나타내며, R2는 하이드록시 또는 C1-C6알킬카르보닐옥시를 나타내고, R3및 R4는 각각 독립적으로 수소, C1-C3, 알킬, 할로겐 또는 C1-C3알킬에 의해 치환되거나 비치환된 페닐, 벤젠환이 할로겐 또는 C1-C3에 의해 치환되거나 비치환된 벤질을 나타낸다.Wherein X may be from 1 to 3, and each independently represents a C 1 -C 3 alkyl or a halogen atom, R 1 is halogen, C 1 -C 2 alkylthio, methoxy, or halogen, C 1 -C C 1 -C 3 alkyl, nitro, R 2 represents hydroxy or C 1 -C 6 alkylcarbonyloxy, R 3 and R 4 each independently represent hydrogen, C 1 -C 3 , Phenyl which is unsubstituted or substituted by alkyl, halogen or C 1 -C 3 alkyl, benzyl wherein the benzene ring is substituted by halogen or C 1 -C 3 .

Description

식물 병원균 퇴치를 위한 신규 피롤-2-온 유도체 및 그의 제조방법Novel pyrrol-2-one derivatives for the control of plant pathogens and their preparation

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is a trivial issue, I did not include the contents of the text.

Claims (13)

하기 일반식(Ⅰ)의 피롤-2-온 유도체.Pyrrol-2-one derivatives of the general formula (I) 상기 식에서 X는 l 내지 3개 존재할 수 있고, 각각 독립적으로 C1-C3알킬 또는 할로겐원자를 나타내고, R1은 할로겐, C1-C2알킬티오, 메톡시, 또는 할로겐, C1-C3알킬, 니트로에 의해 치환되거나 비치환된 페닐을 나타내며, R2는 하이드록시 또는 C1-C6알킬카르보닐옥시를 나타내고, R3및 R4는 각각 독립적으로 수소, C1-C3, 알킬, 할로겐 또는 C1-C3알킬에 의해 치환되거나 비치환된 페닐, 벤젠환이 할로겐 또는 C1-C3에 의해 치환되거나 비치환된 벤질을 나타낸다.Wherein X may be from 1 to 3, and each independently represents a C 1 -C 3 alkyl or a halogen atom, R 1 is halogen, C 1 -C 2 alkylthio, methoxy, or halogen, C 1 -C C 1 -C 3 alkyl, nitro, R 2 represents hydroxy or C 1 -C 6 alkylcarbonyloxy, R 3 and R 4 each independently represent hydrogen, C 1 -C 3 , Phenyl which is unsubstituted or substituted by alkyl, halogen or C 1 -C 3 alkyl, benzyl wherein the benzene ring is substituted by halogen or C 1 -C 3 . 제1항에 있어서, X는 1 내지 3개 존재할 수 있고 각각 독립적으로 C1-C3, 알킬 또는 할로겐원자률 나타내며; R1은 할로겐 또는 C1-C3, 알킬에 의해 치환되거나 비치환된 페닐이고; R2는 하이드록시 또는 C1-C6알킬카르보닐옥시이며; R3및 R4는 각각 독립적으로 수소, C1-C3, 알킬, 할로겐 또는 C1-C3, 알킬에 의해 치환되거나 비치환된 페닐인 역병균(Phtophthora infestans)에 유용한 화합물.The method of claim 1 wherein, X is 1 to 3 may be present and each independently represents a C 1 -C 3, alkyl or halogen atom ratio represents; R 1 is halogen or C 1 -C 3, substituted by alkyl or unsubstituted phenyl; R 2 is hydroxy or C 1 -C 6 alkylcarbonyloxy; R 3 and R 4 are each independently selected from the group consisting of hydrogen, C 1 -C 3 alkyl, halogen or C 1 -C 3 alkyl which is phenyl unsubstituted or substituted by alkyl, Phtophthora infestans. 제1항에 있어서, X는 1 내지 3개 존재할 수 있고, 각각 독립적으로 C1-C3, 알킬을 나타내며; R1은 메톡시이고; R2는 C1-C6알킬카르보닐옥시이며, R3및 R4는 각각 독립적으로 수소 또는 C1-C3알킬인 도열병(Pytophthora oryzae)에 유용한 화합물.2. A compound according to claim 1, wherein X may be present from 1 to 3, and each independently represents C 1 -C 3 alkyl; R < 1 > is methoxy; R 2 is C 1 -C 6 alkylcarbonyloxy and R 3 and R 4 are each independently hydrogen or C 1 -C 3 alkyl, are useful in the Pytophthora oryzae. 제1항에 있어서, X는 1 내지 3개 존재할 수 있고, 각각 독립으로 C1-C3, 알킬 또는 할로겐원자를 나타내며; R1은 할로겐이고; R2는 하이드록시 또는 C1-C6알킬카르보닐옥시이며; R3및 R4는 각각 독립적으로 수소 또는 C1-C3, 알킬인 잿빛 곰팡이병(Botrytis cinerea)에 유용한 화합물.2. The compound of claim 1, wherein X may be present from 1 to 3, and each independently represents a C 1 -C 3 alkyl or halogen atom; R < 1 > is halogen; R 2 is hydroxy or C 1 -C 6 alkylcarbonyloxy; R 3 and R 4 are each independently hydrogen or C 1 -C 3 , alkyl, useful as Botrytis cinerea. 하기 일반식(Ⅲ)의 화합물을 염기 및 용매 존재하에 고리화반응시켜 하기 일반식(I -1)의 화합물을 제도하는 방법.A process for preparing a compound represented by the following general formula (I-1) by cyclizing a compound represented by the following general formula (III) in the presence of a base and a solvent. 상기 식에서, X1, R2, R3및 R4는 제1항에서 정의한 바와 같다.Wherein X 1 , R 2 , R 3 and R 4 are as defined in claim 1. 제5항에 있어서, 염기가 소듐메톡사이드, 소듐에톡사이드, 수소화나트륨, 수소화칼륨 및 테트라부틸암모늄플루오라이드 중에서 선택된 1종인 방법.The process according to claim 5, wherein the base is one selected from the group consisting of sodium methoxide, sodium ethoxide, sodium hydride, potassium hydride and tetrabutylammonium fluoride. 제5항에 있어서, 용매가 톨루엔, 벤젠, 메탄올, 에탄올, 테트라하이드로푸란, 디메톡시에탄 및 디에틸에테르 중에서 선택된 1종인 방법.The process according to claim 5, wherein the solvent is one selected from the group consisting of toluene, benzene, methanol, ethanol, tetrahydrofuran, dimethoxyethane and diethyl ether. 제5항에 있어서, 반응을 0 내지 111℃의 온도에서 수행하는 방법.6. The process according to claim 5, wherein the reaction is carried out at a temperature of from 0 to 111 DEG C. 하기 일반식(I-1)의 화합물을 염기 및 용매 존재하에 하기 일반식(Ⅱ)의 산클로라이드와 반응시킴을 특징으로 하여 하기 일반식(I-2)의 화합물을 제조하는 방법.A process for producing a compound represented by the following general formula (I-2), characterized by reacting a compound represented by the following general formula (I-1) with an acid chloride represented by the following general formula (II) in the presence of a base and a solvent. 상기 식에서, X1, R2, R3및 R4는 제1항에서 정의한 바와 같고, R2'는 제1항에서 정의한 R2와 같으나, 단 하이드록시는 제외하며, R5는 C1-C6알킬을 나타낸다.Wherein R, X 1, R 2, R 3 and R 4 are as defined in claim 1, wherein R 2 'are, but with R 2 as defined in claim 1, except for the end hydroxyl, R 5 is C 1 - It represents a C 6 alkyl. 제9항에 있어서, 염기가 트리에틸아민, 피리딘, 탄산수소나트륨, 탄산나트륨, 탄산수소칼륨 및 탄산칼륨 중에서 선택된 l종인 방법.10. The process of claim 9, wherein the base is selected from the group consisting of triethylamine, pyridine, sodium hydrogencarbonate, sodium carbonate, potassium hydrogencarbonate and potassium carbonate. 제9항에 있어서, 용매가 디클로로메탄, 디클로로에탄, 클로로포름 및 아세토니트릴 중에서 선택된 1종인 방법.The process according to claim 9, wherein the solvent is one selected from the group consisting of dichloromethane, dichloroethane, chloroform and acetonitrile. 제9항에 있어서, 반응을 0 내지 30℃의 온도에서 수행하는 방법.10. The process according to claim 9, wherein the reaction is carried out at a temperature between 0 and 30 < 0 > C. 제1항에 정의된 화합물을 유효성분으로 함유하는 식물병원균 퇴치용 조성물.A composition for combating plant pathogens containing the compound defined in claim 1 as an active ingredient. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: It is disclosed by the contents of the first application.
KR1019960007613A 1996-03-20 1996-03-20 New pyrrol-2-one derivative for controlling phytopathogenic organism and process for preparing the same KR0156680B1 (en)

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