KR950032168A - Novel heterocyclic vinyl sulfides and sulfone compounds and preparation methods thereof - Google Patents

Novel heterocyclic vinyl sulfides and sulfone compounds and preparation methods thereof Download PDF

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KR950032168A
KR950032168A KR1019940010020A KR19940010020A KR950032168A KR 950032168 A KR950032168 A KR 950032168A KR 1019940010020 A KR1019940010020 A KR 1019940010020A KR 19940010020 A KR19940010020 A KR 19940010020A KR 950032168 A KR950032168 A KR 950032168A
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heterocyclic vinyl
following general
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compound
sulfone
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김범태
민용기
박노균
김병섭
조광연
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재단법인 한국화학연구소
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    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
    • C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
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    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/10—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
    • C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
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    • C07—ORGANIC CHEMISTRY
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    • C07D321/02—Seven-membered rings
    • C07D321/04—Seven-membered rings not condensed with other rings
    • C07D321/06—1,3-Dioxepines; Hydrogenated 1,3-dioxepines
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
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    • C07D321/12—Eight-membered rings
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
    • C07D339/02—Five-membered rings
    • C07D339/06—Five-membered rings having the hetero atoms in positions 1 and 3, e.g. cyclic dithiocarbonates

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Abstract

본 발명은 헤테로시클릭 비닐 술파이드 및 술폰계 화합물에 관한 것이다. 좀 더 구체적으로, 본 발명은 하기 일반식(I), (Ⅱ), (Ⅲ) 및 (Ⅳ)로 표시되는 헤테로시클릭 비닐 술파이드 및 술폰계 화합물과 그의 제조방법, 및 살균제로서의 용도에 관한 것이다.The present invention relates to heterocyclic vinyl sulfides and sulfone-based compounds. More specifically, the present invention relates to heterocyclic vinyl sulfides and sulfone compounds represented by the following general formulas (I), (II), (III) and (IV), methods for their preparation, and their use as bactericides. will be.

상기식에서, m은 0 또는 2의 상수를 나타내고; n은 2 내지 8의 정수를 나타내며; 및, X 및 Y는 N, O, S 또는 SO2(단, X의 결합치수가 3인 경우에는 X는 N이다)이다.Wherein m represents a constant of 0 or 2; n represents an integer from 2 to 8; And X and Y are N, O, S or SO 2 (wherein X is N when the bond size of X is 3).

본 발명에 의해 제조된 헤테로시클릭 비닐 술파이드 및 술폰계 화합물은 그 자체로서 살균활성을 갖는 농약의 활성성분으로 이용될 수 있으며, 농약 및 의약의 유효성분을 합성하는 중간체로서도 유용할 것으로 밝혀졌다.The heterocyclic vinyl sulfide and sulfone compounds prepared by the present invention can be used as active ingredients of pesticides having bactericidal activity per se, and have been found to be useful as intermediates for synthesizing active ingredients of pesticides and medicines. .

Description

신규한 헤테로시클릭 비닐 술파이드 및 술폰계 화합물과 그의 제조방법Novel heterocyclic vinyl sulfides and sulfone compounds and preparation methods thereof

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is an open matter, no full text was included.

Claims (16)

하기 일반식(I)로 표시되는 헤테로시클릭 비닐 술파이드 및 술폰계 화합물.Heterocyclic vinyl sulfide and sulfone type compound represented by the following general formula (I). 상기식에서, m은 0 또는 2의 상수를 나타내고; n은 2 내지 8의 정수를 나타내며; 및 X 및 Y는 N, O, S 또는 SO2(단, X의 결합차수가 3인 경우에는 X는 N이다)이다.Wherein m represents a constant of 0 or 2; n represents an integer from 2 to 8; And X and Y are N, O, S or SO 2 (wherein X is N when the bond order of X is 3). 하기 일반식(Ⅱ)로 표시되는 헤테로시클릭 비닐 술파이드 및 술폰계 화합물.Heterocyclic vinyl sulfide and sulfone type compound represented by the following general formula (II). 상기식에서, m, n, X 및 Y는 제1항에 기재한 바와 같다.Wherein m, n, X and Y are as described in claim 1. 하기 일반식(Ⅲ)로 표시되는 헤테로시클릭 비닐 술파이드 및 술폰계 화합물.Heterocyclic vinyl sulfide and sulfone type compound represented by the following general formula (III). 상기식에서, m, X 및 Y는 제1항에 기재한 바와 같다.Wherein m, X and Y are as described in claim 1. 하기 일반식(Ⅳ)로 표시되는 헤테로시클릭 비닐 술파이드 및 술폰계 화합물.Heterocyclic vinyl sulfide and sulfone type compound represented by the following general formula (IV). 상기식에서, m, X 및 Y는 제1항에 기재한 바와 같다.Wherein m, X and Y are as described in claim 1. 하기 구조식(Ⅴ)의 2,2-디플루오로-1-페닐티오스티렌을 염기 존재하에서 1당량의 이중 음이온 친핵체와 반응시켜 하기 일반식(I)의 헤테로시클릭 비닐 술파이드계 화합물을 제조하는 방법.A heterocyclic vinyl sulfide compound of formula (I) is prepared by reacting 2,2-difluoro-1-phenylthiostyrene of formula (V) with 1 equivalent of a double anion nucleophile in the presence of a base. Way. 상기식에서, n, X 및 Y는 제1항에 기재한 바와 같다.Wherein n, X and Y are as described in claim 1. 하기 구조식(Ⅴ)의 2,2-지플루오로-1-페닐티오스티렌을 염기 존재하에서 1당량의 이중 음이온 친핵체와 반응시켜 하기 일반식(Ⅱ)의 헤테로시클릭 비닐 술파이드계 화합물을 제조하는 방법.To prepare a heterocyclic vinyl sulfide compound of formula (II) by reacting 2,2-zifluoro-1-phenylthiostyrene of formula (V) with 1 equivalent of a double anion nucleophile in the presence of a base Way. 상기식에서, n, X 및 Y는 제1항에 기재한 바와 같다.Wherein n, X and Y are as described in claim 1. 하기 구조식(Ⅴ)의 2,2-디플루오로-1-페닐티오스티렌을 염기 존재하에서 1당량의 이중 음이온 친핵체와 반응시켜 하기 일반식(Ⅲ)의 헤테로시클릭 비닐 술파이드계 화합물을 제조하는 방법.To prepare a heterocyclic vinyl sulfide compound of the following general formula (III) by reacting 2,2-difluoro-1-phenylthiostyrene of the following structural formula (V) with 1 equivalent of a double anion nucleophile in the presence of a base Way. 상기식에서, X 및 Y는 제1항에 기재한 바와 같다.Wherein X and Y are as described in claim 1. 하기 구조식(Ⅴ)의 2,2-디플루오로-1-페닐티오스티렌을 염기 존재하에서 1당량의 이중 음이온 친핵체와 반응시켜 하기 일반식(Ⅳ)의 헤테로시클릭 비닐 술파이드계 화합물을 제조하는 방법.To prepare a heterocyclic vinyl sulfide compound of the following general formula (IV) by reacting 2,2-difluoro-1-phenylthiostyrene of the following structural formula (V) with 1 equivalent of a double anion nucleophile in the presence of a base Way. 상기식에서, X 및 Y는 제1항에 기재한 바와 같다.Wherein X and Y are as described in claim 1. 하기 일반식(I)의 헤테로시클릭 비닐 술파이드계 화합물을 산화 반응시켜 하기 일반식(I)의 헤테로시클릭 비닐 술폰계 화합물을 제조하는 방법.A method for producing a heterocyclic vinyl sulfone compound of the following general formula (I) by oxidizing a heterocyclic vinyl sulfide compound of the following general formula (I). 상기식에서, n, X 및 Y는 제1항에 기재한 바와 같다.Wherein n, X and Y are as described in claim 1. 하기 일반식(Ⅱ)의 헤테로시클릭 비닐 술파이드계 화합물을 산화 반응시켜 하기 일반식(Ⅱ)의 헤테로시클릭 비닐 술폰계 화합물을 제조하는 방법.A method for producing a heterocyclic vinyl sulfone compound of the following general formula (II) by oxidizing a heterocyclic vinyl sulfide compound of the following general formula (II). 상기식에서, n, X 및 Y는 제1항에 기재한 바와 같다.Wherein n, X and Y are as described in claim 1. 하기 일반식(Ⅲ)의 헤테로시클릭 비닐 술파이드계 화합물을 산화 반응시켜 하기 일반식(Ⅲ)의 헤테로시클릭 비닐 술폰계 화합물을 제조하는 방법.A method for producing a heterocyclic vinyl sulfone compound of the following general formula (III) by oxidizing a heterocyclic vinyl sulfide compound of the following general formula (III). 상기식에서, X 및 Y는 제1항에 기재한 바와 같다.Wherein X and Y are as described in claim 1. 하기 일반식(Ⅳ)의 헤테로시클릭 비닐 술파이드계 화합물을 산화 반응시켜 하기 일반식(Ⅳ)의 헤테로시클릭 비닐 술폰계 화합물을 제조하는 방법.A method for producing a heterocyclic vinyl sulfone compound of the following general formula (IV) by oxidizing a heterocyclic vinyl sulfide compound of the following general formula (IV). 상기식에서, X 및 Y는 제1항에 기재한 바와 같다.Wherein X and Y are as described in claim 1. 하기 일반식(I)로 표시되는 헤테로시클릭 비닐 술파이드 및 술폰계 화합물 중에서 선택된 1종 이상의 화합물을 유효성분으로 함유하는 살균제.A fungicide containing at least one compound selected from heterocyclic vinyl sulfide and sulfone compounds represented by the following general formula (I) as an active ingredient. 상기식에서, m, n, X 및 Y는 제1항에 기재한 바와 같다.Wherein m, n, X and Y are as described in claim 1. 하기 일반식(Ⅱ)로 표시되는 헤테로시클릭 비닐 술파이드 및 술폰계 화합물 중에서 선택된 1종 이상의 화합물을 유효성분으로 함유하는 살균제.A fungicide containing at least one compound selected from heterocyclic vinyl sulfide and sulfone compounds represented by the following general formula (II) as an active ingredient. 상기식에서, m, n, X 및 Y는 제1항에 기재한 바와 같다.Wherein m, n, X and Y are as described in claim 1. 하기 일반식(Ⅲ)로 표시되는 헤테로시클릭 비닐 술파이드 및 술폰계 화합물 중에서 선택된 1종 이상의 화합물을 유효성분으로 함유하는 살균제.A fungicide containing at least one compound selected from heterocyclic vinyl sulfide and sulfone compounds represented by the following general formula (III) as an active ingredient. 상기식에서, m, X 및 Y는 제1항에 기재한 바와 같다.Wherein m, X and Y are as described in claim 1. 하기 일반식(Ⅳ)로 표시되는 헤테로시클릭 비닐 술파이드 및 술폰계 화합물 중에서 선택된 1종 이상의 화합물을 유효성분으로 함유하는 살균제.A fungicide containing at least one compound selected from heterocyclic vinyl sulfide and sulfone compounds represented by the following general formula (IV) as an active ingredient. 상기식에서, m, X 및 Y는 제1항에 기재한 바와 같다.Wherein m, X and Y are as described in claim 1. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019940010020A 1994-05-07 1994-05-07 Novel heterocyclic vinyl sulfide and sulfone compounds, and process for preparing the same KR0119964B1 (en)

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