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KR830007615A - 피레트 린산과 연관된 시클로프로판 카복실산 에스테르와 그의 제조방법 - Google Patents

피레트 린산과 연관된 시클로프로판 카복실산 에스테르와 그의 제조방법 Download PDF

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KR830007615A
KR830007615A KR1019810003710A KR810003710A KR830007615A KR 830007615 A KR830007615 A KR 830007615A KR 1019810003710 A KR1019810003710 A KR 1019810003710A KR 810003710 A KR810003710 A KR 810003710A KR 830007615 A KR830007615 A KR 830007615A
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쟉끄 마르뗄
쟝 뜨시에르
앙드레 뜨셔
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허버트 후리텔
로우셀 우크라프
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C69/743—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring of acids with a three-membered ring and with unsaturation outside the ring
    • C07C69/747—Chrysanthemumic acid esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • C07D213/647—One oxygen atom attached in position 2 or 6 and having in the molecule an acyl radical containing a saturated three-membered ring, e.g. chrysanthemumic acid esters
    • 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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/105—Aliphatic or alicyclic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/111—Aromatic compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
    • A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
    • A61K31/225—Polycarboxylic acids

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  • Polymers & Plastics (AREA)
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  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Indole Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pyrane Compounds (AREA)
  • Furan Compounds (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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Abstract

내용 없음

Description

피레트 린산과 연관된 시클로프로판 카복실산 에스테르와 그의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (7)

  1. 다음의구조식(I)과 같은 시클로 파라핀 카복실산의 에스테르;
    윗 구조식에서;
    R은 하나 혹은 그 이상의 같거나 서로 다은 기능 그룹으로 치환가능한 C1-C8의 포화나 불포화된 직쇄, 측쇄, 또는 고리형알킬기이거나 하나 또는 그 이상의 기능 그룹으로 치환가능한 C6-C14의 아릴그룹, 또는 하나 또는 그 이상의 같거나 서로 다른 기능 그룹으로 치환가능한 헤텔사이클기이고,
    B는 C1-C18의 직쇄, 측쇄, 또는 고리형의 포화나 불포화된 알킬기이거나 피레트리노이드 계열의 에스테르의 합성에 사용된 알콜의 잔사이며,
    X는 할로겐 원자이고 2중 에틸렌 결합은 Z나 E기하 구조를 갖는다.
  2. R이 (CH2)mO(CH2)n-CH3기 (여기에서, m은 1-8, n은 0-8인 정수이다). 인 상기 1항의 화합물.
  3. B가
    -C1∼C18인 알킬기, 또는,
    -C1∼C4인 알킬기, C2-C6인 알케닐기, C2-C6인 알케닐옥시기,
    C4∼C8인 알카디에닐기, 메틸렌디옥시기, 그리고 할로겐 원자들로 구성되는 그룹에서 선택된 하나 또는 그 이상의 기로 치환 가능한 벤질기, 또는,
    -R1이 수소나 메틸기이고, R2는 모노사이클 아릴기나 -CH-C≡CH 기로서, 특히 5-벤질 3-푸릴 메틸그룹인 다음과 같은 그룹.
    -또는 a가 수소나 메틸기이고, R3는 C2-C6인 지방족 유기 기로서, 특히 -CH2-CH=CH2, CH2-CH=CH-CH3, -CH2-CH=CH-CH=CH2, -CH2-CH=CH-CH2-CH3기들인 다음과 같은 그룹.
    -또는 R1′와 R2′가 서로 같거나 다른 것으로서 수소-할로겐,
    C6∼C10인 아릴기, C2∼C5인 알콕시 카보닐그룹, 또는 시아노그룹인 다음과 같은 그룹.
    -또는 B가 산소나 황, 또는나 -CH2-그룹, 혹은 설폭사이드나 술폰 그룹이고, R4는 수소, -C≡N 기, 메틸기, -CONH2기, CSNH2기, 또는 -C≡CH 기이며, R5는 할로겐이나 메틸기이고,
    n은 0-1인 정수로서 특히 3-페복시벤, α-시아노 3-페녹시 벤질, α-에티닐 3-페녹시벤질, 3-벤조일벤질, 1-(3-페녹시 페닐) 에틸이나 α-티오아미노 3-페녹시 벤질그룹인 다음과 같은 그룹.
    -또는 다음과 같은 그룹.
    -또는 S/I가 방향족사이클이나 유사한 디하이드로로 및 테트라하이드로 고리를 나타내며, R6,R7,R8,R9는 수소, 염소, 또는 메틸기인 다음과 같은 그룹.
    -또는 다음과 같은 그룹.
    -또는 R10이 수소나 CN기, R12가 -CH2-기나 산소,
    R11은 티아졸릴이나 티아디아졸릴기로서결합은 가능한 어느 위치에도 존재할 수 있으며,
    R12는 황원자와 질소원자사이의 탄소에 의해 R1에 부착되어 있는 다음과 같은 그룹.
    -또는 다음과 같은 R13이 수소나 CN 기인 그룹.
    -또는 다음과 같은 그룹.
    -또는 다음과 같은 그룹.
    -또는 R14가 수소, 메틸, 에티닐이나 시아노기이고, R15, R16은 각기 다른 것으로서 수소, 불소, 또는 브롬을 나타내는 다음과 같은 그룹.
    -또는 R17′가 C1-C4의 알킬 그룹, C1-C4의 알콕시그룹, C1-C4의 알킬티오그룹, C1-C4의 알킬 술포닐 그룹, 트리플루오로메틸그룹, 또는 3,4-메틸렌디옥시, 클로로, 플루오로, 또는 브롬그룹이며, P는 0-2의 정수,
    B″는 산소나 황 원자를 나타내는 다음과 같은 그룹.
    -또는 다음과 같은 그룹.
    -또는 다음과 같은 그룹.
    -또는 다음과 같은 그룹.
    -또는 다음과 같은 그룹.
    인 상기 1항의 화합물.
  4. 다음의 구조식(IA)에 따르는 상기 1항의 구조식(I)의 화합물.
    상기식에서,
    A는 산소, 메틸렌그룹, 카보닐그룹, 황, 설폭사이드그룹, 또는 술폰그룹이고,
    R18은 C1-C8인 직쇄나 측쇄알킬기이며, 이중 에틸렌 결합은 (E)나 (Z) 기하구조를 가질수 있는, 치환된 시클로프로판고리는 그의 가능한 모든 입체 이성체 형태로 존재할 수 있다.
  5. 다음의 구조(Ⅱ)와 같은 화합물을 구조(Ⅲ)의 알콜로 처리하고 이를 CO2R 그룹에 대한 선택적인 이탈제와 작용시켜 다음의구조(Ⅳ)인 화합물을 얻은 뒤 이를 R-OH와 작용시켜 그에 따른 구조(I)의 화합물을 얻는 것을 특징으로 하는 상기 1항의 구조식(I)과 같은 화합물의 제조방법.
  6. 다음의 구조(ⅡA)와 같은 산을 구조(ⅢA)와 같은 알콜과 작용시키는 것을 특징으로 하는 상기 4항의 구조(IA)와 같은 화합물의 제조공정.
  7. R이나 R18이 C1-C5인 알킬기인 경우, 구조(Ⅱ)나(ⅡA)의 산은 다음의 구조(V)와 같은 락톤형태의 시스알데히드나 구조(Ⅵ)와 같은 트랜스 알데히드를 위티그(wittig) 반응에 따라 강염기 존재하에서 구조(Ⅶ)의 포스포란과 반응시키거나 구조(Ⅷ)의 포스포네이트와 반응시킴을 특징으로 하는 상기 5항 및 6항에서의 구조(Ⅱ)나 (ⅡA)와 같은 산의 제조방법.
    상기 식에서 R19는 C1-C5의 알킬기,
    R20은 C1-C8의 알킬기를 나타낸다.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019810003710A 1980-10-01 1981-10-02 시클로프로판 카복실산 에스테르의 제조방법 KR880001829B1 (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR8021017A FR2491060A1 (fr) 1980-10-01 1980-10-01 Esters d'acides cyclopropanes carboxyliques apparentes a l'acide pyrethrique, leur procede de preparation et leur application a la lutte contre les parasites
FR80-21017 1980-10-01
FR21017 1980-10-01

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KR830007615A true KR830007615A (ko) 1983-11-04
KR880001829B1 KR880001829B1 (ko) 1988-09-20

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EP (1) EP0050534B1 (ko)
JP (2) JPS57126447A (ko)
KR (1) KR880001829B1 (ko)
AT (1) ATE12490T1 (ko)
AU (1) AU548041B2 (ko)
BR (1) BR8106299A (ko)
CA (2) CA1242648A (ko)
DD (2) DD211473A5 (ko)
DE (1) DE3169688D1 (ko)
DK (2) DK164740C (ko)
ES (1) ES8207133A1 (ko)
FI (1) FI78679C (ko)
FR (2) FR2491060A1 (ko)
GR (1) GR75021B (ko)
HU (1) HU195759B (ko)
IE (1) IE52212B1 (ko)
IL (1) IL63979A0 (ko)
MA (1) MA19293A1 (ko)
NZ (1) NZ198515A (ko)
OA (1) OA07538A (ko)
PT (1) PT73753B (ko)
SU (1) SU1473707A3 (ko)
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ZW (1) ZW24181A1 (ko)

Families Citing this family (25)

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Publication number Priority date Publication date Assignee Title
FR2536392A2 (fr) * 1982-11-22 1984-05-25 Roussel Uclaf Nouveaux derives de l'acide cyclopropane carboxylique, leur procede de preparation et leur application a la lutte contre les parasites
FR2536389B2 (fr) * 1982-11-22 1986-06-27 Roussel Uclaf Esters d'acides cyclopropane carboxyliques apparentes a l'acide pyretrique, leur procede de preparation et leur application a la lutte contre les parasites
FR2491060A1 (fr) * 1980-10-01 1982-04-02 Roussel Uclaf Esters d'acides cyclopropanes carboxyliques apparentes a l'acide pyrethrique, leur procede de preparation et leur application a la lutte contre les parasites
FR2533416B1 (fr) * 1982-09-29 1988-09-02 Roussel Uclaf Nouvelles compositions pesticides renfermant un photostabilisant
FR2534252A1 (fr) * 1982-10-12 1984-04-13 Roussel Uclaf Nouveaux derives de l'acide cyclopropane carboxylique substitues en 3 par une chaine vinylique elle-meme substituee, leur procede de preparation et leur application comme pesticides
FR2535315A1 (fr) * 1982-11-02 1984-05-04 Roussel Uclaf Nouveaux derives de l'acide cyclopropane carboxylique comportant un groupement alcoylthio carbonyle et un atome d'halogene, leur preparation, leur application a la lutte contre les parasites des vegetaux, des animaux et des locaux et les compositions les renfermant
FR2536748A1 (fr) * 1982-11-25 1984-06-01 Roussel Uclaf Nouveaux esters derives d'acides 2,2-dimethyl cyclopropane carboxyliques et d'alcools biaryliques, leur procede de preparation et leur application a la lutte contre les parasites
FR2547817B2 (fr) * 1982-12-15 1986-02-14 Roussel Uclaf Esters d'acides cyclopropane carboxyliques et d'alcools aliphatiques insatures, leur procede de preparation et les compositions pesticides les renfermant
FR2537973B1 (fr) * 1982-12-15 1985-11-08 Roussel Uclaf Esters d'acides cyclopropane carboxyliques et d'alcools aliphatiques insatures, leur procede de preparation et les compositions pesticides les renfermant
FR2569189B1 (fr) * 1984-08-14 1986-12-19 Roussel Uclaf Nouveaux derives du pyrrole, leur procede de preparation et leur application comme pesticides
FR2590259B1 (fr) * 1985-11-20 1989-05-12 Roussel Uclaf Procede de preparation de derives fluores de l'acide phosphonique, et produits obtenus par la mise en oeuvre de ce procede
KR880007430A (ko) * 1986-12-11 1988-08-27 허버트 프리텔 펜타플루오로페닐메틸 2,2-디메틸3-포밀 시클로프로판 카르복실레이트의 제조방법
FR2610624B1 (fr) * 1987-02-06 1989-06-09 Roussel Uclaf Nouveaux esters d'acides cyclopropanecarboxyliques apparentes a l'acide pyrethrique, leur procede de preparation et leur application a la lutte contre les parasites
FR2618432B1 (fr) * 1987-07-20 1989-12-01 Roussel Uclaf Nouveaux derives pyrethrinoides comportant un heterocycle azote, leur procede de preparation et leurs applications comme pesticides
JP2570388B2 (ja) * 1988-06-10 1997-01-08 住友化学工業株式会社 カルボン酸エステルおよびその殺虫剤としての用途
GB8902324D0 (en) * 1989-02-02 1989-03-22 Ici Plc Insecticidal compounds
FR2687666A1 (fr) * 1992-02-21 1993-08-27 Roussel Uclaf Nouveaux esters pyrethrinouiques, derives de l'alcool 6-(trifluoromethyl) benzylique, leur procede de preparation et leur application comme pesticides.
FR2693082B1 (fr) * 1992-07-01 1994-08-26 Roussel Uclaf Nouvelles compositions insecticides renfermant comme principe actif un ester de l'acide 3-[(DELTAZ) 2-fluoro 3-oxo 3-méthoxy propényl] cyclopropane carboxylique.
FR2703044B1 (fr) * 1993-03-25 1995-06-02 Roussel Uclaf Nouveau procédé d'isomérisation de doubles liaisons.
JP3694915B2 (ja) * 1994-06-17 2005-09-14 住友化学株式会社 エステル化合物およびそれを有効成分とする有害生物防除剤
EP0729949A2 (en) * 1995-03-01 1996-09-04 Sumitomo Chemical Company, Limited 1,2,4-Triazol-3-ones as pesticides
JP3286598B2 (ja) * 1998-06-11 2002-05-27 富士写真フイルム株式会社 シートの搬送装置
JP4552456B2 (ja) * 2004-02-27 2010-09-29 住友化学株式会社 エステル化合物およびその用途
JP5066843B2 (ja) * 2006-06-15 2012-11-07 住友化学株式会社 エステル化合物及びその有害生物防除用途
CN106642346A (zh) * 2016-12-28 2017-05-10 武汉海尔电器股份有限公司 空调器

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ES505887A0 (es) 1982-09-01
DK164740C (da) 1992-12-28
DK164402B (da) 1992-06-22
EP0050534A1 (fr) 1982-04-28
FI813042L (fi) 1982-04-02
OA07538A (fr) 1985-03-31
ATE12490T1 (de) 1985-04-15
ZA816768B (en) 1982-09-29
JPS57126447A (en) 1982-08-06
DD202422A5 (de) 1983-09-14
MA19293A1 (fr) 1982-04-01
ZW24181A1 (en) 1982-02-24
JPS6254421B2 (ko) 1987-11-14
BR8106299A (pt) 1982-06-22
KR880001829B1 (ko) 1988-09-20
AU548041B2 (en) 1985-11-21
IE812274L (en) 1982-04-01
NZ198515A (en) 1985-03-20
DK164402C (da) 1992-11-09
GR75021B (ko) 1984-07-12
JPH0643369B2 (ja) 1994-06-08
IL63979A0 (en) 1982-01-31
FR2491060A1 (fr) 1982-04-02
CA1242648A (fr) 1988-10-04
FR2491060B1 (ko) 1983-09-16
PT73753B (fr) 1983-11-08
SU1473707A3 (ru) 1989-04-15
DK15691D0 (da) 1991-01-29
DK164740B (da) 1992-08-10
DK432781A (da) 1982-04-02
PT73753A (fr) 1981-10-01
CA1237135A (fr) 1988-05-24
AU7596181A (en) 1982-04-08
FR2560189B2 (fr) 1987-12-11
DK15691A (da) 1991-01-29
FR2560189A2 (fr) 1985-08-30
HU195759B (en) 1988-07-28
FI78679B (fi) 1989-05-31
IE52212B1 (en) 1987-08-05
EP0050534B1 (fr) 1985-04-03
DD211473A5 (de) 1984-07-18
JPS6023343A (ja) 1985-02-05
FI78679C (fi) 1989-09-11
ES8207133A1 (es) 1982-09-01
DE3169688D1 (en) 1985-05-09

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