KR950017954A - 피롤의 알콕시메틸화 - Google Patents

피롤의 알콕시메틸화 Download PDF

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Publication number
KR950017954A
KR950017954A KR1019940040706A KR19940040706A KR950017954A KR 950017954 A KR950017954 A KR 950017954A KR 1019940040706 A KR1019940040706 A KR 1019940040706A KR 19940040706 A KR19940040706 A KR 19940040706A KR 950017954 A KR950017954 A KR 950017954A
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KR
South Korea
Prior art keywords
sub
halogen
haloalkyl
hydrogen
alkoxy
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KR1019940040706A
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English (en)
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프랜시스 도우너 로버트
마이클 바아턴 제리
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알퐁스 아아르 노에
아메리칸 사이아나밋드 캄파니
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Application filed by 알퐁스 아아르 노에, 아메리칸 사이아나밋드 캄파니 filed Critical 알퐁스 아아르 노에
Publication of KR950017954A publication Critical patent/KR950017954A/ko

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    • 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
    • C07D207/32—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
    • C07D207/325—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 with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
    • C07D207/327—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • C07D207/32—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
    • C07D207/325—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 with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
    • 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

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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)
  • Pyrrole Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Detergent Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

적절한 피롤 전구체를 연속적으로 디알콕시메탄, 빌스미디어 시약 및 삼차아민과 반응시켜 다양한 피롤 화합물의 고리 질소 원자 상에 알콕시메틸기를 도입시키는 안전하고 효과적인 수단이 제공된다. 생성물 1-(알콕시메틸)피롤은 살충제, 진드기 구충제, 선충박멸제 및 연체동물 박멸제로서 유용하다.

Description

피롤의 알콕시메틸화
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (10)

1-H-피롤 화합물을 비 양성자성 용매의 존재 하에서 디-(알콕시)메탄, 디메틸포름아미드 및 옥시염호인과 반응시켜 반응 혼합물을 형성하고 그 반응 혼합물을 임의적으로 높은 온도에서, 삼차 아민으로 처리하는 것으로 구성되는 1-(알콕시메틸)피롤 화합물의 제조 방법.
제1항에 있어서, 1-H-피롤 화합물이 하기 일반식 Ⅰ의 화합물인 방법:
상기 식에서 W는 CN, NO2, S(O)nCR 또는 CNR1R2이고 X는 수소, 할로겐, CN, NO2, S(O)mCR3, C1-C4할로알킬, Q, 또는 하나 이상의 할로겐, NO2, CN, C1-C4할로알킬, C1-C4알콕시 또는 C1-C4할로알콕시 기로 임의 치환된 페닐이고; Y는 수소, 할로겐, C1-C4할로알킬 또는 하나 이상의 할로겐, NO3, CN, C1-C4알킬, C1-C4할로알킬, C1-C4알콕시 또는 C1-C4할로알콕시 기로 임의 치환된 페닐이고; Z는 수소, 할로겐 또는 C1-C4할로알킬이고; n 및 m은 각각 독립적으로 0, 1 또는 2의 정수이고; R 및 R3은 각각 독립적으로 C1-C6할로알킬이고; R1및 R2는 각각 독립적으로 C1-C4알킬, C1-C4할로알킬 또는 하나 이상의 할로겐, NO2, CN, C1-C4알킬, C1-C4할로알킬, C1-C4알콕시 또는 C1-C4할로알콕시 기로 임의 치환된 페닐이고; Q는
R4, R5및 R6는 각각 독립적으로 수소, 할로겐, NO2, CHO이거나 R5및 R6는 그들이 부착되어 있는 원자와 함께 취해져서 R5R6가 하기 구조식;
으로 나타내어지는 고리를 형성할 수 있고; R7, R8, R8및 R10은 각각 독립적으로 수소, 할로겐, CN 또는 NO2이며; A 및 A1은 각각 독립적으로 O 또는 S이다.
제2항에 있어서, W는 CN 또는 NO2이고; X는 할로겐, C1-C4할로알킬 또는 하나 이상의 할로겐 또는 C1-C4할로알킬기로 임의 치환된 페닐이고; Y가 수소, 할로겐 또는 C1-C4할로알킬이며; Z가 수소, 할로겐 또는 C1-C4할로알킬이다.
제1항에 있어서, 비양성자성 용매가 방향족 탄화수소 또는 지방족 니트릴인 방법.
제4항에 있어서, 용매가 톨루엔, 크실렌 또는 아세토니트릴인 방법.
제1항에 있어서, 삼차 아민이 트리(C1-C6알킬)아민인 방법.
제6항에 있어서, 아민이 트리에틸아민인 방법.
제1항에 있어서, 1-(알콕시메틸)피롤 화합물이 1-(C1-C6알콕시메틸)피롤 화합물이고 디-(알콕시)메탄이 디-(C1-C6알콕시)메탄인 방법.
제8항에 있어서, 디-(C1-C6알콕시)메탄이 디-(에톡시)메탄인 방법.
제9항에 있어서, 1-H-피롤 화합물이 하기 구조식을 갖는 방법:
※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019940040706A 1993-12-29 1994-12-28 피롤의 알콕시메틸화 KR950017954A (ko)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US08/174,999 US5359090A (en) 1993-12-29 1993-12-29 Alkoxymethylation of pyrroles
US08/174999 1993-12-29

Publications (1)

Publication Number Publication Date
KR950017954A true KR950017954A (ko) 1995-07-22

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Country Status (20)

Country Link
US (1) US5359090A (ko)
EP (1) EP0669318B1 (ko)
JP (1) JP3746801B2 (ko)
KR (1) KR950017954A (ko)
CN (1) CN1055464C (ko)
AT (1) ATE168369T1 (ko)
AU (1) AU681725B2 (ko)
BR (1) BR9405282A (ko)
CA (1) CA2139045C (ko)
CZ (1) CZ286316B6 (ko)
DE (1) DE69411701T2 (ko)
DK (1) DK0669318T3 (ko)
ES (1) ES2119049T3 (ko)
HU (1) HU213027B (ko)
IL (1) IL112158A (ko)
RU (1) RU2137758C1 (ko)
SK (1) SK279455B6 (ko)
TW (1) TW282454B (ko)
UA (1) UA39935C2 (ko)
ZA (1) ZA9410361B (ko)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6271392B1 (en) * 1994-10-07 2001-08-07 Rhone-Poulenc Inc. Intermediates useful for the synthesis of 1-arylpyrrole pesticides
BR9608502A (pt) * 1995-06-07 1999-07-06 Nippon Shinyaku Co Ltd Derivado da pirrola e composição medicinal
US5817834A (en) * 1998-02-09 1998-10-06 American Cyanamid Company Process for the preparation of 2-aryl-5-(perfluoro-alkyl) pyrrole compounds from N-(perfluoroalkyl-methyl) arylimidoyl chloride compounds
US6133455A (en) * 1998-02-09 2000-10-17 American Cyanamid Company Process for the preparation of 2-aryl-5(perfluoro-alkyl) pyrrole compounds from N-(arylmethylene)-1-chloro-1-(perfluoroalkyl) methylamine compounds
US5965773A (en) * 1998-02-09 1999-10-12 American Cyanamid Company Process for the preparation of 2-aryl-5-(perfluoroalkyl) pyrrole compounds from N-(perfluoroalkylmethyl) arylimidoyl chloride compounds
US6011161A (en) * 1998-02-09 2000-01-04 American Cyanamid Company Process for the preparation of 2-aryl-5-(perfluoroalkyl)pyrrole compounds from N-(perfluoro-alkylmethyl)arylimidoyl chloride compounds
US6320059B1 (en) 2000-03-07 2001-11-20 American Cyanamid Company Process for the preparation of 2-aryl-5-(perfluoro-alkyl) pyrrole compounds from N-[1-chloro-1-(perfluoroalkyl) methyl] arylimidoyl chloride compounds
JP5628787B2 (ja) 2009-02-25 2014-11-19 武田薬品工業株式会社 ピロール化合物の製造法
CN102617439A (zh) * 2012-02-27 2012-08-01 山东潍坊双星农药有限公司 一种溴虫腈的制备方法
CN104016899A (zh) * 2014-05-16 2014-09-03 浙江师范大学 一种溴虫腈的合成方法
AU2016259360B1 (en) * 2016-11-16 2017-09-07 Rotam Agrochem International Company Limited A novel crystalline form of chlorfenapyr, a process for its preparation and use of the same
MX2019010998A (es) * 2017-03-13 2019-10-17 Basf Agro Bv Produccion de compuestos de arilpirrol en presencia de una base de dipea.
CN109006823B (zh) * 2018-09-11 2021-05-07 江苏省血吸虫病防治研究所 2-芳基取代吡咯类化合物在杀钉螺药物中的应用
CN109006824B (zh) * 2018-09-11 2021-04-27 江苏省血吸虫病防治研究所 2-芳基取代吡咯类化合物在杀双脐螺药物中的应用
CN115286551A (zh) * 2022-04-15 2022-11-04 陕西美邦药业集团股份有限公司 一种虫螨腈及类似物的制备方法

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US4500738A (en) * 1983-12-08 1985-02-19 American Home Products Corporation Preparation of alkoxy methyl ethers
US5010098A (en) * 1987-07-29 1991-04-23 American Cyanamid Company Arylpyrrole insecticidal acaricidal and nematicidal agents and methods for the preparation thereof
BR8906202A (pt) * 1988-12-05 1990-09-25 American Cyanamid Co Processo e composicao para o controle de pragas de insetos,acaros e moluscos,composto para tal controle e processo para sua preparacao
US5204332A (en) * 1988-12-05 1993-04-20 American Cyanamid Company Pyrrole carbonitrile and nitropyrrole insecticidal and acaricidal and molluscicidal agents
US5371239A (en) * 1989-12-22 1994-12-06 American Cyanamid Company Methods and compositions for protecting animals against attack and infestation by helminth, acarid and arthropod endo- and ectoparasites
US5151536A (en) * 1990-12-17 1992-09-29 American Cyanamid Company Process for the manufacture of pesticidal 1-(alkoxymethyl) pyrrole compounds

Also Published As

Publication number Publication date
ES2119049T3 (es) 1998-10-01
AU681725B2 (en) 1997-09-04
RU94045268A (ru) 1996-10-27
CA2139045A1 (en) 1995-06-30
SK158094A3 (en) 1995-08-09
HU213027B (en) 1997-01-28
IL112158A (en) 1999-10-28
JP3746801B2 (ja) 2006-02-15
CN1055464C (zh) 2000-08-16
RU2137758C1 (ru) 1999-09-20
US5359090A (en) 1994-10-25
CA2139045C (en) 2005-07-26
JPH07242627A (ja) 1995-09-19
BR9405282A (pt) 1995-10-17
DE69411701D1 (de) 1998-08-20
DK0669318T3 (da) 1998-11-02
IL112158A0 (en) 1995-03-15
CZ318794A3 (en) 1995-09-13
EP0669318A1 (en) 1995-08-30
CN1106798A (zh) 1995-08-16
ATE168369T1 (de) 1998-08-15
ZA9410361B (en) 1995-09-05
SK279455B6 (sk) 1998-11-04
UA39935C2 (uk) 2001-07-16
EP0669318B1 (en) 1998-07-15
TW282454B (ko) 1996-08-01
CZ286316B6 (cs) 2000-03-15
DE69411701T2 (de) 1998-11-12
AU8176194A (en) 1995-07-06
HUT69061A (en) 1995-08-28
HU9403802D0 (en) 1995-03-28

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