MD70C2 - Method for obtaining the isomeric cypermetrine mixture - Google Patents
Method for obtaining the isomeric cypermetrine mixtureInfo
- Publication number
- MD70C2 MD70C2 MD94-0138A MD940138A MD70C2 MD 70 C2 MD70 C2 MD 70C2 MD 940138 A MD940138 A MD 940138A MD 70 C2 MD70 C2 MD 70C2
- Authority
- MD
- Moldova
- Prior art keywords
- trans
- mixture
- izopropanol
- antioxidant
- hexane
- Prior art date
Links
Classifications
-
- 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
Landscapes
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to the carbonic nitryl acids, namely to the obtaining of cypermetrine mixture that contains in a ecchymolar proportion a enantiomeric couple of 1R trans and S-and 1S trans-R-isomer - with the structural formulathat manifests an insecticide activity. The aim is the finding of some more active compounds from the indicated class.These are to be obtained from a mixture that contains eight isomers in isopropan or diisopropyl ether in the presence of an antioxidant or the initial mixter that contain trans isomers is to be dissolved in the presence of an antioxidant in izopropan oil ether, hexane, reptane, cyclohexane, methanol, hexane in mixture with CCIn or izopropanol and oil ether in the presence of an antioxidant and of a basa as for exemple 2-amino-benzimidazol, basec ion changing or in izopropanol and oil ether in the presence of a base as for example diazobiciclo-(4,3,0)-en-5, ammoniumsodium's carbonate ammonium's hydroxide or in tret-C1- C4-alkylamine, di-C1-C4-alkylamine at 15-60°C. In the obtained solution or directly in the initial mixture a crystallization agent is introduced. It consists of the enantiomeric couplt 1R-trans-S and 1S-trans-R, is to be cooled till the temperature from +30 till -30°C, the hurried crystals are separated, and then the mume solution is evaporated. As a oxidizer 2,6 ditret-butyl-4-methylphenye is used in the hexane or izopropanol.
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HU85158A HU198612B (en) | 1985-01-16 | 1985-01-16 | Arthropodicide comprising determined stereo isomers of pyrethroid as active ingredient and process for producing the active ingredients |
HU8674A HU198373B (en) | 1986-01-08 | 1986-01-08 | Artropodicide composition containing trans-cipermetrin isomeres and process for producing the active components |
PCT/HU1986/000004 WO1986004216A1 (en) | 1985-01-16 | 1986-01-16 | Insecticidal composition comprising more than one active ingredients |
SU864028150A SU1579454A3 (en) | 1985-01-16 | 1986-09-15 | Method of obtaining isomeric mixture |
Publications (2)
Publication Number | Publication Date |
---|---|
MD70B1 MD70B1 (en) | 1994-10-31 |
MD70C2 true MD70C2 (en) | 1995-01-31 |
Family
ID=26317151
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
MD94-0138A MD70C2 (en) | 1985-01-16 | 1994-04-21 | Method for obtaining the isomeric cypermetrine mixture |
Country Status (17)
Country | Link |
---|---|
US (4) | US4845126A (en) |
EP (2) | EP0215010B1 (en) |
JP (2) | JPH0621111B2 (en) |
KR (2) | KR870700004A (en) |
AR (1) | AR240225A1 (en) |
AU (1) | AU581732B2 (en) |
BG (2) | BG60226B1 (en) |
BR (2) | BR8604534A (en) |
CA (1) | CA1275108A (en) |
DD (2) | DD264913B3 (en) |
DE (2) | DE3670194D1 (en) |
DK (2) | DK159712C (en) |
ES (3) | ES8705376A1 (en) |
MD (1) | MD70C2 (en) |
NO (3) | NO166682C (en) |
PT (2) | PT81856B (en) |
WO (2) | WO1986004216A1 (en) |
Families Citing this family (24)
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 |
DE3522629A1 (en) * | 1985-06-25 | 1987-01-08 | Bayer Ag | METHOD FOR PRODUCING SPECIFIC ENANTIOMER PAIRS OF PERMETHRINIC ACID (ALPHA) CYANO-3-PHENOXY-4-FLUOR-BENZYL ESTERS |
US4997970A (en) * | 1987-06-15 | 1991-03-05 | Fmc Corporation | Conversion of pyrethroid isomers to move active species |
HU205839B (en) * | 1987-11-18 | 1992-07-28 | Chinoin Gyogyszer Es Vegyeszet | Synergetic artropodicide composition containining pirethroides and phosphate-esters as active components |
HU198830B (en) * | 1988-02-05 | 1989-12-28 | Chinoin Gyogyszer Es Vegyeszet | Arthropodicides comprising cypermethrin trans-isomers and tetramethrin |
US5189062A (en) * | 1988-04-07 | 1993-02-23 | Chinoin Gyogyszer -Es Vegyeszeti Termekek Gyara R.T. | Plant protecting agent |
HU204393B (en) * | 1988-12-22 | 1992-01-28 | Chinoin Gyogyszer Es Vegyeszet | Insecticide aqouos solutions containing piretroides as active components and microemulsion compositions containing former solutions |
GEP20002025B (en) | 1989-01-17 | 2000-04-10 | Chinoin Diodser Esh Bidieceti Diara Rt Hu | The Stable Arthropodicidal Composition |
MD282C2 (en) * | 1989-01-17 | 1996-01-31 | Chinoin Gyogyszer -Es Vegyeszeti Termekek Gyara Rt. | Method of obtaining a mixture of cypermethrin isomers in form of stabilized crystalline product |
DE69001866T2 (en) * | 1989-01-17 | 1993-09-23 | Chinoin Gyogyszer Es Vegyeszet | METHOD FOR PRODUCING CYPERMETHRIN ISOMERS. |
HU210098B (en) * | 1989-12-27 | 1995-02-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing isomeric mixtures of cypermethrin and stabilised insecticidal compositions and concentrates containing the mixtures |
HU206605B (en) * | 1989-07-31 | 1992-12-28 | Chinoin Gyogyszer Es Vegyeszet | Synergetic artropodicide compositions containing pyrethroides as active components |
DK0426948T3 (en) | 1989-08-11 | 1996-05-28 | American Cyanamid Co | Aryl pyrrols such as insecticidal, acaricidal and nematodicidal agents as well as methods for their preparation |
US5128497A (en) * | 1990-01-03 | 1992-07-07 | Fmc Corporation | Conversion of pyrethroid isomers to more active species |
US5164411A (en) * | 1991-01-25 | 1992-11-17 | Fmc Corporation | Pyrethroid compositions |
EP0601237A1 (en) * | 1992-12-09 | 1994-06-15 | Duphar International Research B.V | Method of preparing optically active cyanohydrin derivatives |
HUT69381A (en) * | 1993-12-09 | 1995-09-28 | Egyt Gyogyszervegyeszeti Gyar | Process for producing (2-chloro pyridyl)-7-azabicyclo [2.2.1.]heptane |
LV12032B (en) * | 1995-04-24 | 1998-09-20 | ARGO-CHEMIE Novenyvedoszer Gyarto Ertekesito es Forgalmazo Kft. | METHODS OF PESTICIDE COMPOSITIONS AND THEIR ACQUISITION |
HUP9603007A1 (en) * | 1996-10-31 | 1998-10-28 | Chinoin Gyógyszer és Vegyészeti Termékek Gyára Rt. | Arthropodal agents and process for producing the same |
CN100525612C (en) * | 2002-04-24 | 2009-08-12 | 拜尔作物科学股份有限公司 | Composition for luring and controlling arthropods comprising synthetic silicic acid and protein autolysate |
US8110608B2 (en) | 2008-06-05 | 2012-02-07 | Ecolab Usa Inc. | Solid form sodium lauryl sulfate (SLS) pesticide composition |
DE102010023586A1 (en) * | 2010-06-12 | 2011-12-15 | Saltigo Gmbh | Synergistic mixtures of α, ω-Aminalkohol enantiomers, their preparation and their use in insect and mite repellent preparations |
CN101915809B (en) * | 2010-07-01 | 2012-10-17 | 王冬群 | Detection method of pyrethroid pesticide remained in rice |
US8968757B2 (en) | 2010-10-12 | 2015-03-03 | Ecolab Usa Inc. | Highly wettable, water dispersible, granules including two pesticides |
Family Cites Families (26)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4024163A (en) * | 1972-05-25 | 1977-05-17 | National Research Development Corporation | Insecticides |
US4031239A (en) * | 1975-02-13 | 1977-06-21 | American Cyanamid Company | Cyclopropanecarboxylates for systemic control of ectoparasites |
FR2375161A1 (en) * | 1976-04-23 | 1978-07-21 | Roussel Uclaf | PROCESS FOR TRANSFORMATION OF AN OPTICALLY ACTIVE A-CYANE SECONDARY ALCOHOL CHIRAL ACID ESTER OF STRUCTURE (R) INTO A-CYANE SECONDARY ALCOHOL CHIRAL ACID ESTER OF STRUCTURE (S) |
FR2402411A1 (en) * | 1977-09-08 | 1979-04-06 | Roussel Uclaf | APPLICATION AS A PESTICIDE, IN THE FIGHT AGAINST MITES AND AGAINST NEMATODES PARASITES OF PLANTS, OF ESTERS OF CYCLOPROPANE CARBOXYLIC ACIDS WITH DIHALOVINYL CHAIN AND THE COMPOSITIONS OF ACARICIDES AND NEMATICIDES CONTAINING THEM |
EP0005826B1 (en) * | 1978-05-30 | 1985-09-11 | The Wellcome Foundation Limited | Synergistic pyrethroid formulations and their preparation |
US4308279A (en) * | 1979-06-06 | 1981-12-29 | Fmc Corporation | Crystalline, insecticidal pyrethroid |
US4261921A (en) * | 1979-06-06 | 1981-04-14 | Fmc Corporation | Process for preparation of a crystalline insecticidal pyrethroid enantiomer pair |
DE2928986A1 (en) * | 1979-07-18 | 1981-02-05 | Bayer Ag | (+) - CIS AND (+) TRANS-2,2-DIMETHYL- 3- (2,2-DICHLOR-VINYL) -CYCLOPROPAN-1-CARBONIC ACID - (+ -) - ALPHA -CYANO-3-PHENOXY4-FLUOR- BENZYL ESTER, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS INSECTICIDES AND ACARICIDES |
JPS5657756A (en) * | 1979-10-15 | 1981-05-20 | Sumitomo Chem Co Ltd | Preparation of more highly active carboxylic ester |
JPS5657755A (en) * | 1979-10-15 | 1981-05-20 | Sumitomo Chem Co Ltd | Preparation of more highly active carboxylic ester |
CA1150301A (en) * | 1979-11-27 | 1983-07-19 | Michael J. Bull | Cyclopropane carboxylic acid ester derivatives |
CA1162560A (en) * | 1980-04-23 | 1984-02-21 | Ronald F. Mason | Process for preparing cyclopropane carboxylic acid ester derivatives |
CA1150730A (en) * | 1980-04-23 | 1983-07-26 | Michael J. Bull | Process for preparing cyclopropane carboxylic acid ester derivatives |
CA1162561A (en) * | 1981-05-26 | 1984-02-21 | Derek A. Wood | Preparation of cyanobenzyl cyclopropane carboxylates |
US4524150A (en) * | 1982-04-12 | 1985-06-18 | E. I. Du Pont De Nemours And Company | Stabilized mixtures of carbamate insecticides and synthetic pyrethroids |
ZA836964B (en) * | 1982-10-11 | 1984-05-30 | Ici Plc | Insecticidal product and preparation thereof |
GB8308507D0 (en) * | 1983-03-28 | 1983-05-05 | Ici Plc | Insecticidal product |
DE3372480D1 (en) * | 1982-10-18 | 1987-08-20 | Ici Plc | Insecticidal product and preparation thereof |
CA1206483A (en) * | 1982-11-11 | 1986-06-24 | Johannes Van Berkel | Process for preparing cyclopropane carboxylic acid ester derivatives |
JPS59227806A (en) * | 1983-06-10 | 1984-12-21 | Sumitomo Chem Co Ltd | Insecticidal composition |
DE3401483A1 (en) * | 1984-01-18 | 1985-07-25 | Bayer Ag, 5090 Leverkusen | METHOD FOR PRODUCING SPECIFIC ENANTIOMER PAIRS OF PERMETHRINIC ACID (ALPHA) -CYANO-3-PHENOXY-4-FLUOR-BENZYL ESTERS |
GB8418331D0 (en) * | 1984-07-18 | 1984-08-22 | Ici Plc | Insecticidal ester |
GB8422872D0 (en) * | 1984-09-11 | 1984-10-17 | Ici Plc | Insecticidal product |
CA1275108A (en) * | 1985-01-16 | 1990-10-09 | Laszlo Pap | Insecticidal composition comprising more than one active ingredients |
US4997970A (en) * | 1987-06-15 | 1991-03-05 | Fmc Corporation | Conversion of pyrethroid isomers to move active species |
US5028731A (en) * | 1989-11-17 | 1991-07-02 | Fmc Corporation | Preparation of mixtures of cypermethrin or cyfluthrin isomers enriched in more active species |
-
1986
- 1986-01-15 CA CA000499624A patent/CA1275108A/en not_active Expired - Fee Related
- 1986-01-16 AU AU53542/86A patent/AU581732B2/en not_active Expired
- 1986-01-16 WO PCT/HU1986/000004 patent/WO1986004216A1/en active Application Filing
- 1986-01-16 PT PT81856A patent/PT81856B/en not_active IP Right Cessation
- 1986-01-16 ES ES551465A patent/ES8705376A1/en not_active Expired
- 1986-01-16 JP JP61500734A patent/JPH0621111B2/en not_active Expired - Fee Related
- 1986-01-16 DD DD86310743A patent/DD264913B3/en not_active IP Right Cessation
- 1986-01-16 AR AR302871A patent/AR240225A1/en active
- 1986-01-16 DE DE8686900830T patent/DE3670194D1/en not_active Expired - Fee Related
- 1986-01-16 ES ES551467A patent/ES8802602A1/en not_active Expired
- 1986-01-16 WO PCT/HU1986/000003 patent/WO1986004215A1/en active Application Filing
- 1986-01-16 DD DD86286250A patent/DD255471A5/en unknown
- 1986-01-16 BR BR8604534A patent/BR8604534A/en not_active IP Right Cessation
- 1986-01-16 EP EP86900830A patent/EP0215010B1/en not_active Expired - Lifetime
- 1986-01-16 PT PT81857A patent/PT81857B/en not_active IP Right Cessation
- 1986-01-16 EP EP86900829A patent/EP0208758B1/en not_active Expired
- 1986-01-16 DE DE8686900829T patent/DE3665002D1/en not_active Expired
- 1986-01-16 US US06/916,546 patent/US4845126A/en not_active Expired - Lifetime
- 1986-01-16 BR BR8604535A patent/BR8604535A/en not_active IP Right Cessation
- 1986-09-10 KR KR860700628A patent/KR870700004A/en not_active Application Discontinuation
- 1986-09-15 DK DK440886A patent/DK159712C/en not_active IP Right Cessation
- 1986-09-15 DK DK440786A patent/DK159711C/en not_active IP Right Cessation
- 1986-09-15 BG BG076425A patent/BG60226B1/en unknown
- 1986-09-15 NO NO863681A patent/NO166682C/en not_active IP Right Cessation
- 1986-09-15 NO NO863682A patent/NO166831C/en not_active IP Right Cessation
- 1986-09-15 BG BG76424A patent/BG47645A3/en unknown
- 1986-09-16 KR KR1019860700640A patent/KR870700005A/en not_active Application Discontinuation
-
1988
- 1988-07-13 ES ES557848A patent/ES8900001A1/en not_active Expired
-
1989
- 1989-06-16 US US07/367,546 patent/US5013754A/en not_active Expired - Lifetime
- 1989-06-19 US US07/371,650 patent/US4963584A/en not_active Expired - Lifetime
-
1990
- 1990-09-07 NO NO90903920A patent/NO169957C/en not_active IP Right Cessation
-
1991
- 1991-04-30 JP JP3126865A patent/JPH0825982B2/en not_active Expired - Fee Related
- 1991-05-07 US US07/696,580 patent/US5110976A/en not_active Expired - Lifetime
-
1994
- 1994-04-21 MD MD94-0138A patent/MD70C2/en active IP Right Grant
Non-Patent Citations (2)
Title |
---|
Brevet CH nr. 646419, Int. cl. C 07 C 121/75, 1984. * |
Spravocinic po pestiţidam/ Pod red. L. Melnicova, M., 1985, s. 151, 227. * |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
FG4A | Patent for invention issued | ||
IF99 | Valid patent on 19990615 |
Free format text: EXPIRES: 20060115 |