KR920703518A - 보다 활성인 종의 함량이 많은 사이퍼메트린 또는 사이플루트린 이성체 혼합물의 제조방법 - Google Patents
보다 활성인 종의 함량이 많은 사이퍼메트린 또는 사이플루트린 이성체 혼합물의 제조방법Info
- Publication number
- KR920703518A KR920703518A KR1019920701159A KR920701159A KR920703518A KR 920703518 A KR920703518 A KR 920703518A KR 1019920701159 A KR1019920701159 A KR 1019920701159A KR 920701159 A KR920701159 A KR 920701159A KR 920703518 A KR920703518 A KR 920703518A
- Authority
- KR
- South Korea
- Prior art keywords
- configuration
- phenoxyphenylacetonitrile
- hydroxy
- acid chloride
- cyfluthrin
- Prior art date
Links
- 239000005946 Cypermethrin Substances 0.000 title claims description 3
- QQODLKZGRKWIFG-QSFXBCCZSA-N cyfluthrin Chemical compound CC1(C)[C@@H](C=C(Cl)Cl)[C@H]1C(=O)O[C@@H](C#N)C1=CC=C(F)C(OC=2C=CC=CC=2)=C1 QQODLKZGRKWIFG-QSFXBCCZSA-N 0.000 title claims description 3
- 229960001591 cyfluthrin Drugs 0.000 title claims description 3
- 229960005424 cypermethrin Drugs 0.000 title claims description 3
- KAATUXNTWXVJKI-UHFFFAOYSA-N cypermethrin Chemical compound CC1(C)C(C=C(Cl)Cl)C1C(=O)OC(C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 KAATUXNTWXVJKI-UHFFFAOYSA-N 0.000 title claims description 3
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 239000000203 mixture Substances 0.000 title claims description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 6
- GXUQMKBQDGPMKZ-UHFFFAOYSA-N 2-hydroxy-2-(3-phenoxyphenyl)acetonitrile Chemical compound N#CC(O)C1=CC=CC(OC=2C=CC=CC=2)=C1 GXUQMKBQDGPMKZ-UHFFFAOYSA-N 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- -1 2,2-dichloroethenyl Chemical group 0.000 claims 1
- SFBGIISWPCQUIL-UHFFFAOYSA-N 2,3-dimethylcyclopropane-1-carbonyl chloride Chemical compound CC1C(C1C)C(=O)Cl SFBGIISWPCQUIL-UHFFFAOYSA-N 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 230000000361 pesticidal effect Effects 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/38—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by esterified hydroxy groups
- C07C255/39—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by esterified hydroxy groups with hydroxy groups esterified by derivatives of 2,2-dimethylcyclopropane carboxylic acids, e.g. of chrysanthemumic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Instrument Panels (AREA)
- Digital Computer Display Output (AREA)
- Controls And Circuits For Display Device (AREA)
Abstract
Description
Claims (8)
- 불활성 대기중 75 내지 1150℃의 온도에서 산 수용체의 부재하에서, 적절한 α-하이드록시-3-페녹시페닐아세토니트릴을 탄화수소 용매중의 3-(2,2-디클로로에테닐)-2,2-디메틸사이클로프로판카보닐 클로라이드의 용액과 반응시키고, 반응 혼합물을 수성 염기로 세척한 후, 생성물을 회수함을 특징으로 하는, 보다 살충활성이 큰 이성체의 함량이 많은 사이퍼메트린 또는 사이플루트린의 이성체 혼합물의 제조방법.
- 제1항에 있어서, α-하이드록시-3-페녹시페닐아세토니트릴이 R, S배위를 가지며, 산 클로라이드가 R, S-시스/트랜스 배위를 가짐을 특징으로 하는 방법.
- 제1항에 있어서, α-하이드록시-3-페녹시페닐아세토니트릴이 R, S배위를 가지며, 산 클로라이드가 R, S-시스 배위를 가짐을 특징으로 하는 방법.
- 제1항에 있어서, α-하이드록시-3-페녹시페닐아세토니트릴이 R, S배위를 가지며, 산 클로라이드가 R, S-트랜스 배위를 가짐을 특징으로 하는 방법.
- 제1항에 있어서, α-하이드록시-3-페녹시페닐아세토니트릴이 S배위를 가지며, 산 클로라이드가 R, S-시스/트랜스 배위를 가짐을 특징으로 하는 방법.
- 제1항에 있어서, α-하이드록시-3-페녹시페닐아세토니트릴이 S배위를 가지며, 산 클로라이드가 R, S-시스 배위를 가짐을 특징으로 하는 방법.
- 제1항에 있어서, α-하이드록시-3-페녹시페닐아세토니트릴이 S배위를 가지며, 산 클로라이드가 R, S-트랜스 배위를 가짐을 특징으로 하는 방법.
- ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US438,657 | 1989-11-17 | ||
US07/438,657 US5028731A (en) | 1989-11-17 | 1989-11-17 | Preparation of mixtures of cypermethrin or cyfluthrin isomers enriched in more active species |
PCT/US1990/005578 WO1991007379A1 (en) | 1989-11-17 | 1990-10-01 | Preparation of mixtures of cypermethrin or cyfluthrin isomers enriched in more active species |
Publications (2)
Publication Number | Publication Date |
---|---|
KR920703518A true KR920703518A (ko) | 1992-12-18 |
KR940011906B1 KR940011906B1 (ko) | 1994-12-27 |
Family
ID=23741488
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019920701159A KR940011906B1 (ko) | 1989-11-17 | 1990-10-01 | 보다 활성인 종의 함량이 많은 사이퍼메트린 또는 사이플루트린 이성체 혼합물의 제조방법 |
Country Status (17)
Country | Link |
---|---|
US (1) | US5028731A (ko) |
EP (1) | EP0500572B1 (ko) |
JP (1) | JPH0662536B2 (ko) |
KR (1) | KR940011906B1 (ko) |
BR (1) | BR9007850A (ko) |
CA (1) | CA2068532C (ko) |
DE (1) | DE69025478T2 (ko) |
DK (1) | DK0500572T3 (ko) |
ES (1) | ES2085916T3 (ko) |
HU (1) | HU208304B (ko) |
IL (1) | IL96298A (ko) |
MX (1) | MX171955B (ko) |
RU (1) | RU2060990C1 (ko) |
TR (1) | TR25423A (ko) |
TW (1) | TW200447B (ko) |
WO (1) | WO1991007379A1 (ko) |
ZA (1) | ZA908570B (ko) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA1275108A (en) * | 1985-01-16 | 1990-10-09 | Laszlo Pap | Insecticidal composition comprising more than one active ingredients |
US5164411A (en) * | 1991-01-25 | 1992-11-17 | Fmc Corporation | Pyrethroid compositions |
US9107416B2 (en) * | 2005-12-22 | 2015-08-18 | Fmc Corporation | Insecticidal and miticidal mixtures of bifenthrin and cyano-pyrethroids |
CA2836135A1 (en) * | 2011-05-26 | 2012-11-29 | Allergy Technologies, Llc | Compositions and methods for treating materials with insecticides and potentiating agents |
WO2019145221A1 (en) | 2018-01-29 | 2019-08-01 | BASF Agro B.V. | New agrochemical formulations |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2769835A (en) * | 1953-12-09 | 1956-11-06 | Monsanto Chemicals | Process of producing alkyl acrylates by dehydrohalogenation using an anhydrous calcium sulfate catalyst |
US3078306A (en) * | 1958-04-24 | 1963-02-19 | Basf Ag | Process for the production of alphachloroximes and their hydrochlorides |
US3082236A (en) * | 1959-04-29 | 1963-03-19 | Wallace & Tiernan Inc | Peroxy esters of p-menthane hydroperoxides |
US4024163A (en) * | 1972-05-25 | 1977-05-17 | National Research Development Corporation | Insecticides |
DE2850502A1 (de) * | 1977-11-24 | 1979-05-31 | Ciba Geigy Ag | 2,4,4,4-tetrachlorbuttersaeure-1,2,4, 4,4-pentachlor-but-1-enylester |
DE2928986A1 (de) * | 1979-07-18 | 1981-02-05 | Bayer Ag | (+)-cis und (+) trans-2,2-dimethyl- 3-(2,2-dichlor-vinyl)-cyclopropan-1- carbonsaeure-(+-) - alpha -cyano-3-phenoxy4-fluor-benzylester, verfahren zu ihrer herstellung sowie ihre verwendung als insektizide und akarizide |
FR2471369A1 (fr) * | 1979-12-17 | 1981-06-19 | Roussel Uclaf | Nouvelles imines, derivant d'esters d'acides formyl cyclopropane carboxyliques, leur procede de preparation et leur application a la preparation d'esters insecticides |
DE3200484A1 (de) * | 1982-01-09 | 1983-07-21 | Bayer Ag, 5090 Leverkusen | Aminoalkylester, verfahren zu ihrer herstellung und ihre verwendung in schaedlingsbekaempfungsmittel |
JPS60202843A (ja) * | 1984-03-27 | 1985-10-14 | Sumitomo Chem Co Ltd | エステル誘導体の合成方法 |
JP2982339B2 (ja) * | 1991-02-25 | 1999-11-22 | ソニー株式会社 | 光ディスクカートリッジと光ディスク装置 |
-
1989
- 1989-11-17 US US07/438,657 patent/US5028731A/en not_active Expired - Lifetime
-
1990
- 1990-10-01 JP JP2514365A patent/JPH0662536B2/ja not_active Expired - Lifetime
- 1990-10-01 KR KR1019920701159A patent/KR940011906B1/ko not_active IP Right Cessation
- 1990-10-01 WO PCT/US1990/005578 patent/WO1991007379A1/en active IP Right Grant
- 1990-10-01 HU HU921627A patent/HU208304B/hu unknown
- 1990-10-01 CA CA002068532A patent/CA2068532C/en not_active Expired - Fee Related
- 1990-10-01 BR BR909007850A patent/BR9007850A/pt not_active IP Right Cessation
- 1990-10-01 DE DE69025478T patent/DE69025478T2/de not_active Expired - Fee Related
- 1990-10-01 ES ES90915553T patent/ES2085916T3/es not_active Expired - Lifetime
- 1990-10-01 DK DK90915553.3T patent/DK0500572T3/da active
- 1990-10-01 EP EP90915553A patent/EP0500572B1/en not_active Expired - Lifetime
- 1990-10-01 RU SU905052420A patent/RU2060990C1/ru not_active IP Right Cessation
- 1990-10-23 TW TW079108928A patent/TW200447B/zh active
- 1990-10-25 ZA ZA908570A patent/ZA908570B/xx unknown
- 1990-11-09 IL IL9629890A patent/IL96298A/en not_active IP Right Cessation
- 1990-11-14 TR TR90/1096A patent/TR25423A/xx unknown
- 1990-11-16 MX MX023375A patent/MX171955B/es unknown
Also Published As
Publication number | Publication date |
---|---|
IL96298A0 (en) | 1991-08-16 |
KR940011906B1 (ko) | 1994-12-27 |
CA2068532C (en) | 1995-05-16 |
EP0500572A4 (en) | 1992-10-07 |
JPH05501110A (ja) | 1993-03-04 |
EP0500572B1 (en) | 1996-02-21 |
HUT62554A (en) | 1993-05-28 |
WO1991007379A1 (en) | 1991-05-30 |
US5028731A (en) | 1991-07-02 |
HU9201627D0 (en) | 1993-04-28 |
CA2068532A1 (en) | 1991-05-18 |
RU2060990C1 (ru) | 1996-05-27 |
MX171955B (es) | 1993-11-24 |
IL96298A (en) | 1995-10-31 |
HU208304B (en) | 1993-09-28 |
DE69025478D1 (de) | 1996-03-28 |
ES2085916T3 (es) | 1996-06-16 |
BR9007850A (pt) | 1992-10-06 |
TR25423A (tr) | 1993-03-01 |
ZA908570B (en) | 1991-08-28 |
EP0500572A1 (en) | 1992-09-02 |
DK0500572T3 (da) | 1996-06-24 |
JPH0662536B2 (ja) | 1994-08-17 |
DE69025478T2 (de) | 1996-10-24 |
TW200447B (ko) | 1993-02-21 |
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