KR840007401A - 플루오로아졸릴프로판 유도체의 제조방법 - Google Patents

플루오로아졸릴프로판 유도체의 제조방법 Download PDF

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KR840007401A
KR840007401A KR1019830006339A KR830006339A KR840007401A KR 840007401 A KR840007401 A KR 840007401A KR 1019830006339 A KR1019830006339 A KR 1019830006339A KR 830006339 A KR830006339 A KR 830006339A KR 840007401 A KR840007401 A KR 840007401A
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alkyl
formula
alkoxy
substituted
halogen
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KR1019830006339A
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KR880001813B1 (ko
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우르스뮐러, (외 2)
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아놀드 자일러 에른스트알테르
시바-가이기에이. 지
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
    • 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

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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)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

Abstract

내용 없음.

Description

플루오로아졸릴프로판 유도체의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (24)

  1. 다음식(II)의 플루오로아 졸릴 메틸 옥시란과 다음식(III)의 티올알콜 또는 알콜을 염기 및 불활성 용매의 존재하에 반응시키고 이 결과의 식(Ia) 화합물들을 다음 식(IV)의 에테르 또는 에스테르화제로에테르 또는 에스테르화 하는 단계로 구성되는 다음식(I)의 플루오로 아졸릴프로판 유도체의 제조방법.
  3. 상기식에서, Az는 이미다졸릴 또는 트리아졸릴이고, R1은 수소, 알킬 또는 수소, 알킬, 알콕시, 할로게 노알킬, 니트로, 시아노, 카르복실 또는 알콕시카르보닐로 치환 또는 비치환된 아랄킬이고, R2는 알콕시, 아랄콕시 또는 페닐로 치환 또는 비치환된 C1-10알킬로서 이것은 할로겐, 알킬, 알콕시, 할로게노알킬, 카르복실 또는 알콕시 카르보닐로 치환 또는 비치환된 아랄콕시 및 페닐의 방향족 핵이될 수 있으며, R3는 수소, 알킬, 알킬카르보닐 또는 할로겐, 알콕시, 알킬, 할로게노알킬, 시아노, 카르복실 또는 알콕시 카르보닐로 치환 또는 비치환된 아랄킬이고, R5는 C1-8알킬, C3-8시클로알킬, C2-6알케닐, C3-6알키닐, 페닐, 나프틸, 비페닐, 벤질페닐, 벤질옥시페닐, 페녹시페닐 및 아랄킬에서 선택되는 비치환 또는 단일치환 또는 다중치환된 라디칼이고, X는 산소 또는 황이며, Y는 할로겐 원자 또는 유기 또는 무기산 라디칼임.
  4. 제1항에 있어서, 용매가 N,N-디메틸포름아미드, N, -디메틸아세타미드, 디메틸설폭시드, 아세토니트릴, 벤조니트릴 또는 이것과 다른 알맞은 용매를 혼합시켜서 제조한 용매인 방법.
  5. 제1항에 있어서, Az가 이미다졸릴 또는 1,2,4-트리아졸릴이고, R1은 수소, 할로겐 또는 시아노로 치환된 또는 비치환 C1-6알킬 또는 할로겐, C1-3알킬, C1-3알콕시, C1-3할로 게노 알킬, 니트로 시아노,카르복실 또는 C1-6알콕시카르보닐로 치환 또는 비치환된 C1-3페닐알킬이고, R2는 C1-3알콕시, 페닐 또는 C1-3페닐알킬로 치환 또는 비치환된 C1-10알킬로서, 이것은 할로겐, C1-3알킬, C1-3알콕시, C1-3할로게노알킬, 니트로, 시아노, 카르복실 또는 C1-6알콕시카르보닐로 치환 또는 비치환된 페닐핵이 될 수 있고, R3는 수소, C1-6알킬, C1-6알킬카르보닐 또는 할로겐, C1-3알콕시, C1-3알킬, C1-3할로게노알릴, 시아노, 카르복실 또는 C1-6알콕시카르보닐로 치환 또는 비치환된 C1-3페닐알킬이고, R5는 C1-8알콕시, C3-8시클로알킬, C3-6알케닐, C3-6알키닐, 페닐, 나프틸, 비페닐, 벤진페닐, 벤질옥시페닐, 페녹시페닐 및 아랄킬에서 선택된 비치환 또는 단일치환 또는 다중치환된 라디칼로서 치횐체는 할로겐, 시아노, C1-3알킬, C1-5알콕시, C1-5할로게노알킬, C1-3알킬티오, C1-3</SB할로게노알킬티오, 니트로 및 티오시아노인 것에서 선택되고, X는 산소 또는 황인 제조방법.
  6. 제1항에 있어서, Az가 1,2,4-트리아졸릴인 방법.
  7. 제1항에 있어서, R2가 C1-6알킬 또는 할로겐으로 치환 또는 비치환된 벤질인 방법.
  8. 제5항에 있어서 R2가 테트라부틸 또는 i-프로필인 방법.
  9. 제1항에 있어서 R1과 R3가 수소 또는 C1-4알킬인 방법.
  10. 제1항에 있어서 R5가 할로겐 치환된 페닐인 방법.
  11. 제1항에 있어서, R5가 4위치가 할로겐으로 치환된 페닐인 방법.
  12. 제1항에 있어서 X가 산인 방법.
  13. 제1항에 있어서 Az가 1,2,4-트리아졸일이고, R1과 R3는 수소 또는 C1-4알킬이고, R2는 t-부틸 또는 i-프로필이고, R5는 4위치가 할로겐 치환된 페닐이고 X는 산소인 방법.
  14. 제1항에 있어서, 1-(4-플루오로페녹시)-2-t-부틸-2-히드록시-3-플루오로-3-(1H-1,2,4-트리아졸-1-일)프로판, 1-(4-플루오로페녹시)-2-부틸-2-히드록시-3-플루오로-3-메틸-3-(1H-1,2,4-트리아졸-1-일) 프로판, 1-(4-클로로페녹시)-2-t-부틸-2-히드록시-3-플루오로-3-(1H-1,2,4-트리아졸-1-일)프로판. 1-(4-클로로페녹시)-2-t-부틸-2-히드록시-3-플루오로-3-메틸-3-(1H-1,2,4-트리아졸-1-일)프로판 및 1-(4-메틸페녹시)-2-t-부틸-2-히드록시-3-플루오로-3-메틸-3-(1H-1,2,4-트리아졸-1-일)프로판에서 선택한 화합물이 제조되는 방법.
  15. 염기의 존재하에 식(V)의 플루오로아졸릴케톤을 식(VI)의 할로게노케톤과 식(VII)의 아졸을 반응시켜서 제조하는 방법.
  17. 상기식에서 각 치환체는 제1항에서 정의한 대로임.
  18. 제12항에 있어서 식(VIII)의 아졸릴메틸케톤과 식(IX)의 화합물을 염기의 존재하에 반응시켜서 식(V)의 플루오로아졸릴 케톤을 제조하는 방법.
  20. 상기식에서 Z는 할로겐 또는 유기 또는 무기 라디칼이고, 나머지 치환기는 식(I)의 기설명에서 정의한대로임.
  21. 제1항에 있어서 식(V)의 케톤과 디메틸설포늄 메틸리드, 디메틸옥소설포늄 메틸리드 또는 대응하는 염과 강염기 및 반응에 불활성인 극성용매에서 반응시켜서 식(I)의 플루오로아졸릴 메틸 옥시란을 제조하는 방법.
  23. 상기식에서 각 치환기는 식(I)에서 정의한 대로임.
  24. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019830006339A 1983-01-10 1983-12-30 플루오로아졸릴 프로판 유도체의 제조방법 KR880001813B1 (ko)

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CH11283 1983-01-10
CH112/83-4 1983-01-10

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KR840007401A true KR840007401A (ko) 1984-12-07
KR880001813B1 KR880001813B1 (ko) 1988-09-19

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US (1) US4758670A (ko)
EP (1) EP0116262B1 (ko)
JP (1) JPS59130875A (ko)
KR (1) KR880001813B1 (ko)
AR (1) AR240671A1 (ko)
AT (1) ATE48995T1 (ko)
AU (1) AU571860B2 (ko)
BR (1) BR8400056A (ko)
CA (1) CA1222518A (ko)
DE (1) DE3381012D1 (ko)
ES (1) ES8505355A1 (ko)
IL (1) IL70621A (ko)
MY (1) MY101395A (ko)
PH (1) PH21578A (ko)
ZA (1) ZA84161B (ko)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100237084B1 (ko) * 1997-08-01 2000-01-15 전재구 난연성 견지 및 그의 제조방법

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3470881D1 (de) * 1983-12-20 1988-06-09 Ciba Geigy Ag Microbizides
US5194263A (en) * 1989-01-20 1993-03-16 Allied Colloids Limited Particulate materials, their production and use
US5460817A (en) * 1988-01-19 1995-10-24 Allied Colloids Ltd. Particulate composition comprising a core of matrix polymer with active ingredient distributed therein
DE3825841A1 (de) * 1988-07-29 1990-02-01 Basf Ag 1-halogen-1-azolypropene und -methyloxirane und diese enthaltende fungizide

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DE2918894A1 (de) * 1979-05-10 1980-11-20 Bayer Ag Fluorierte 1-triazolyl-butan-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide
DE2938534A1 (de) * 1979-09-24 1981-04-23 Bayer Ag, 5090 Leverkusen Acylierte triazolyl-(gamma)-fluorpinakolyl-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide
DE2948206A1 (de) * 1979-11-30 1981-06-25 Basf Ag, 6700 Ludwigshafen Fungizide (gamma) -azolyl-verbindungen, ihre herstellung und verwendung
AU542623B2 (en) * 1980-05-16 1985-02-28 Bayer Aktiengesellschaft 1-hydroxyethyl-azole derivatives
DE3033592A1 (de) * 1980-09-06 1982-04-22 Bayer Ag, 5090 Leverkusen Fluorierte 1-azolyl-butan-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide
DE3279417D1 (en) * 1981-03-18 1989-03-09 Ici Plc Triazole compounds, a process for preparing them, their use as plant fungicides and fungicidal compositions containing them
PH19709A (en) * 1982-11-23 1986-06-16 Ciba Geigy Ag Microbicidal 1-carbonyl-1-phenoxyphenyl-2-azolylethanol derivatives
DE3314738A1 (de) * 1983-04-23 1984-10-25 Bayer Ag, 5090 Leverkusen Azolylethyl-benzyl-ether-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide
DE3470881D1 (de) * 1983-12-20 1988-06-09 Ciba Geigy Ag Microbizides

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100237084B1 (ko) * 1997-08-01 2000-01-15 전재구 난연성 견지 및 그의 제조방법

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US4758670A (en) 1988-07-19
EP0116262B1 (de) 1989-12-27
BR8400056A (pt) 1984-08-14
IL70621A0 (en) 1984-04-30
IL70621A (en) 1987-12-31
CA1222518A (en) 1987-06-02
EP0116262A3 (en) 1986-12-17
AR240671A1 (es) 1990-08-31
MY101395A (en) 1991-10-23
DE3381012D1 (de) 1990-02-01
ZA84161B (en) 1984-09-26
AU2310684A (en) 1984-07-12
JPS59130875A (ja) 1984-07-27
ES528698A0 (es) 1985-06-01
KR880001813B1 (ko) 1988-09-19
ATE48995T1 (de) 1990-01-15
AU571860B2 (en) 1988-04-28
ES8505355A1 (es) 1985-06-01
PH21578A (en) 1987-12-11
EP0116262A2 (de) 1984-08-22

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