MD70C2 - Method for obtaining the isomeric cypermetrine mixture - Google Patents

Method for obtaining the isomeric cypermetrine mixture

Info

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
Application number
MD94-0138A
Other languages
Romanian (ro)
Russian (ru)
Other versions
MD70B1 (en
Inventor
Gyorgy Hidasi
Szekely Istvan Dr.
Bela Bertok
Sandor Zoltan
Lajos Nagy
GAJARI Antal DR.
Somfai Eva Dr.
Agnes Hegedus
Pap Laszlo Dr.
Soos Rudolf Dr.
Erzsebet Radvany
Botar Sandor Dr.
Szabolcsi Tamas Dr.
Original Assignee
Chinoin Gyogyszer -Es Vegyeszeti Termekek Gyara Rt.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from HU85158A external-priority patent/HU198612B/en
Priority claimed from HU8674A external-priority patent/HU198373B/en
Application filed by Chinoin Gyogyszer -Es Vegyeszeti Termekek Gyara Rt. filed Critical Chinoin Gyogyszer -Es Vegyeszeti Termekek Gyara Rt.
Publication of MD70B1 publication Critical patent/MD70B1/en
Publication of MD70C2 publication Critical patent/MD70C2/en

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)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (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.
MD94-0138A 1985-01-16 1994-04-21 Method for obtaining the isomeric cypermetrine mixture MD70C2 (en)

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) DD255471A5 (en)
DE (2) DE3670194D1 (en)
DK (2) DK159712C (en)
ES (3) ES8802602A1 (en)
MD (1) MD70C2 (en)
NO (3) NO166682C (en)
PT (2) PT81857B (en)
WO (2) WO1986004216A1 (en)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
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
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
GEP20002025B (en) 1989-01-17 2000-04-10 Chinoin Diodser Esh Bidieceti Diara Rt Hu The Stable Arthropodicidal Composition
ES2057531T3 (en) * 1989-01-17 1994-10-16 Chinoin Gyogyszer Es Vegyeszet PROCEDURE FOR THE PREPARATION OF CYPERMETRINE 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
EP0426948B1 (en) 1989-08-11 1996-05-08 American Cyanamid Company Arylpyrrole insecticidal acaricidal and nematicidal agents and methods
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
AP2002A (en) * 2002-04-24 2009-05-18 Bayer Cropscience Sa 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)

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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
JPS5657755A (en) * 1979-10-15 1981-05-20 Sumitomo Chem Co Ltd Preparation of more highly active carboxylic ester
JPS5657756A (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
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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

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
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. *

Also Published As

Publication number Publication date
NO863681L (en) 1986-09-15
DD255471A5 (en) 1988-04-06
US5110976A (en) 1992-05-05
DD264913A5 (en) 1989-02-15
JPS62501708A (en) 1987-07-09
CA1275108A (en) 1990-10-09
JPH0621111B2 (en) 1994-03-23
NO166682C (en) 1991-08-28
NO863682L (en) 1986-09-15
AR240225A1 (en) 1990-03-30
ES8802602A1 (en) 1988-11-01
NO166831C (en) 1991-09-11
NO863682D0 (en) 1986-09-15
ES8900001A1 (en) 1988-11-16
NO903920D0 (en) 1990-09-07
EP0215010A1 (en) 1987-03-25
NO903920L (en) 1986-09-15
DE3670194D1 (en) 1990-05-17
DK440886A (en) 1986-09-15
NO166831B (en) 1991-06-03
AU5354286A (en) 1986-08-13
DK159711B (en) 1990-11-26
ES557848A0 (en) 1988-11-16
EP0208758B1 (en) 1989-08-16
DD264913B3 (en) 1992-11-19
US5013754A (en) 1991-05-07
PT81856B (en) 1987-11-30
JPH05201949A (en) 1993-08-10
NO863681D0 (en) 1986-09-15
KR870700004A (en) 1987-02-28
NO166682B (en) 1991-05-21
US4963584A (en) 1990-10-16
EP0208758A1 (en) 1987-01-21
DK159712C (en) 1991-04-29
WO1986004215A1 (en) 1986-07-31
ES8705376A1 (en) 1987-05-16
DK440786D0 (en) 1986-09-15
BG60226B2 (en) 1994-01-18
ES551467A0 (en) 1988-11-01
DK440786A (en) 1986-09-15
DK440886D0 (en) 1986-09-15
WO1986004216A1 (en) 1986-07-31
PT81857B (en) 1987-11-30
DE3665002D1 (en) 1989-09-21
AU581732B2 (en) 1989-03-02
BG60226B1 (en) 1994-01-24
PT81857A (en) 1986-02-01
DK159712B (en) 1990-11-26
JPH0825982B2 (en) 1996-03-13
MD70B1 (en) 1994-10-31
US4845126A (en) 1989-07-04
NO169957C (en) 1992-08-26
AU5354186A (en) 1986-08-13
EP0215010B1 (en) 1990-04-11
ES551465A0 (en) 1987-05-16
PT81856A (en) 1986-02-01
BR8604534A (en) 1987-07-14
DK159711C (en) 1991-04-29
AU581731B2 (en) 1989-03-02
BR8604535A (en) 1987-07-14
NO169957B (en) 1992-05-18
BG47645A3 (en) 1990-08-15
KR870700005A (en) 1987-02-28

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Legal Events

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FG4A Patent for invention issued
IF99 Valid patent on 19990615

Free format text: EXPIRES: 20060115