MD70C2 - Способ получения изомерной смеси циперметрина - Google Patents

Способ получения изомерной смеси циперметрина

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
English (en)
Romanian (ro)
Other versions
MD70B1 (ro
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/hu
Priority claimed from HU8674A external-priority patent/HU198373B/hu
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/xx
Publication of MD70C2 publication Critical patent/MD70C2/ru

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

Изобретение относится к нитритам карбоновых кислот в частности к получению изомерой смеси циперметрина, содержащей в эквимолярном соотношении энантиомерную пару 1R транс-S- и 1S транс-R-изомеров структурной формулыкоторая проявляет инсектицидную активность. Цель - выявление новых более активных соединений указанного класса. Получение ведут из смеси, состоящей из восьми изомеров в изопропаноле или диизопропиловом эфире, в присутствии антиоксиданта, или растворяют исходную смесь, состоящую из транс-изомеров, в присутствии антиоксиланта в изопропаноле, петролейном эфире, гексане, гептане, циклогексане, метаноле гексане в смеси с CCl4 или изопропаноле и петролейном эфире в присутстии антиоксиданта и основания, такого как 2-амино-бензимидазол, основная ионообменная смола, или в изопропаноле и петролейном эфире в присутстии основания такого как диазобицикло-(4,3,0)-ен-5, аммиак, карбонат натрия, гидроксид аммония, или в трет-С1-С4-алкиламине, ди-С1-С4-алкиламине при 15-60°С. В полученный раствор или непосредственно в исходную смесь вносят затравку, состоящую из эвантиомерной пары 1R-транс-S- и 1S-транс-R, охлаждают до температуры от +30 до -30°С, отделяют выпавшие кристаллы с последующим выпариванием маточного раствора. В качестве антиоксиданта используют 2,6-дитрет-бутил-4-метилфенол в изопропаноле или гексане. 1 з.п. ф-лы, 10 табл.
MD94-0138A 1985-01-16 1994-04-21 Способ получения изомерной смеси циперметрина MD70C2 (ru)

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 (ru) 1985-01-16 1986-09-15 Способ получени изомерной смеси циперметрина

Publications (2)

Publication Number Publication Date
MD70B1 MD70B1 (ro) 1994-10-31
MD70C2 true MD70C2 (ru) 1995-01-31

Family

ID=26317151

Family Applications (1)

Application Number Title Priority Date Filing Date
MD94-0138A MD70C2 (ru) 1985-01-16 1994-04-21 Способ получения изомерной смеси циперметрина

Country Status (17)

Country Link
US (4) US4845126A (ru)
EP (2) EP0215010B1 (ru)
JP (2) JPH0621111B2 (ru)
KR (2) KR870700004A (ru)
AR (1) AR240225A1 (ru)
AU (1) AU581732B2 (ru)
BG (2) BG60226B1 (ru)
BR (2) BR8604534A (ru)
CA (1) CA1275108A (ru)
DD (2) DD255471A5 (ru)
DE (2) DE3670194D1 (ru)
DK (2) DK159712C (ru)
ES (3) ES8802602A1 (ru)
MD (1) MD70C2 (ru)
NO (3) NO166682C (ru)
PT (2) PT81857B (ru)
WO (2) WO1986004216A1 (ru)

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 (de) * 1985-06-25 1987-01-08 Bayer Ag Verfahren zur herstellung bestimmter enantiomerenpaare von permethrinsaeure-(alpha)-cyano-3-phenoxy-4-fluor-benzyl -ester
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 (ru) * 1989-01-17 1996-01-31 Chinoin Gyogyszer -Es Vegyeszeti Termekek Gyara Rt. Способ получения смеси изомеров циперметрина в форме стабилизированного кристаллического продукта
GEP20002025B (en) 1989-01-17 2000-04-10 Chinoin Diodser Esh Bidieceti Diara Rt Hu The Stable Arthropodicidal Composition
ES2057531T3 (es) * 1989-01-17 1994-10-16 Chinoin Gyogyszer Es Vegyeszet Procedimiento para la preparacion de isomeros de cipermetrina.
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 (hu) * 1996-10-31 1998-10-28 Chinoin Gyógyszer és Vegyészeti Termékek Gyára Rt. Arthropodicid szerek és eljárás előállításukra
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 (de) * 2010-06-12 2011-12-15 Saltigo Gmbh Synergistisch wirkende Mischungen aus α-,ω-Aminalkohol-Enantiomeren, deren Herstellung und ihre Verwendung in insekten- und milbenabwehrenden Zubereitungen
CN101915809B (zh) * 2010-07-01 2012-10-17 王冬群 一种大米中拟除虫菊酯类农药残留的检测方法
US8968757B2 (en) 2010-10-12 2015-03-03 Ecolab Usa Inc. Highly wettable, water dispersible, granules including two pesticides

Family Cites Families (26)

* Cited by examiner, † Cited by third party
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 (fr) * 1976-04-23 1978-07-21 Roussel Uclaf Procede de transformation d'un ester d'acide chiral d'alcool secondaire a-cyane optiquement actif de structure (r) en ester d'acide chiral d'alcool secondaire a-cyane de structure (s)
FR2402411A1 (fr) * 1977-09-08 1979-04-06 Roussel Uclaf Application comme pesticide, dans la lutte contre les acariens et contre les nematodes parasites des vegetaux, d'esters d'acides cyclopropane carboxyliques a chaine dihalovinylique et les compositions acaricides et nematicides les renfermant
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 (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
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
GB8308507D0 (en) * 1983-03-28 1983-05-05 Ici Plc Insecticidal product
ZA836964B (en) * 1982-10-11 1984-05-30 Ici Plc Insecticidal product and preparation thereof
GB2128607A (en) * 1982-10-18 1984-05-02 Ici Plc An enantiomeric pair of cyhalothrin isomers and process for preparation thereof
CA1206483A (en) * 1982-11-11 1986-06-24 Johannes Van Berkel Process for preparing cyclopropane carboxylic acid ester derivatives
JPS59227806A (ja) * 1983-06-10 1984-12-21 Sumitomo Chem Co Ltd 殺虫組成物
DE3401483A1 (de) * 1984-01-18 1985-07-25 Bayer Ag, 5090 Leverkusen Verfahren zur herstellung bestimmter enantiomerenpaare von permethrinsaeure-(alpha)-cyano-3-phenoxy-4-fluor-benzyl-ester
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
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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 (no) 1986-09-15
DD255471A5 (de) 1988-04-06
US5110976A (en) 1992-05-05
DD264913A5 (de) 1989-02-15
JPS62501708A (ja) 1987-07-09
CA1275108A (en) 1990-10-09
JPH0621111B2 (ja) 1994-03-23
NO166682C (no) 1991-08-28
NO863682L (no) 1986-09-15
AR240225A1 (es) 1990-03-30
ES8802602A1 (es) 1988-11-01
NO166831C (no) 1991-09-11
NO863682D0 (no) 1986-09-15
ES8900001A1 (es) 1988-11-16
NO903920D0 (no) 1990-09-07
EP0215010A1 (en) 1987-03-25
NO903920L (no) 1986-09-15
DE3670194D1 (de) 1990-05-17
DK440886A (da) 1986-09-15
NO166831B (no) 1991-06-03
AU5354286A (en) 1986-08-13
DK159711B (da) 1990-11-26
ES557848A0 (es) 1988-11-16
EP0208758B1 (en) 1989-08-16
DD264913B3 (de) 1992-11-19
US5013754A (en) 1991-05-07
PT81856B (pt) 1987-11-30
JPH05201949A (ja) 1993-08-10
NO863681D0 (no) 1986-09-15
KR870700004A (ko) 1987-02-28
NO166682B (no) 1991-05-21
US4963584A (en) 1990-10-16
EP0208758A1 (en) 1987-01-21
DK159712C (da) 1991-04-29
WO1986004215A1 (en) 1986-07-31
ES8705376A1 (es) 1987-05-16
DK440786D0 (da) 1986-09-15
BG60226B2 (en) 1994-01-18
ES551467A0 (es) 1988-11-01
DK440786A (da) 1986-09-15
DK440886D0 (da) 1986-09-15
WO1986004216A1 (en) 1986-07-31
PT81857B (pt) 1987-11-30
DE3665002D1 (en) 1989-09-21
AU581732B2 (en) 1989-03-02
BG60226B1 (bg) 1994-01-24
PT81857A (en) 1986-02-01
DK159712B (da) 1990-11-26
JPH0825982B2 (ja) 1996-03-13
MD70B1 (ro) 1994-10-31
US4845126A (en) 1989-07-04
NO169957C (no) 1992-08-26
AU5354186A (en) 1986-08-13
EP0215010B1 (en) 1990-04-11
ES551465A0 (es) 1987-05-16
PT81856A (en) 1986-02-01
BR8604534A (pt) 1987-07-14
DK159711C (da) 1991-04-29
AU581731B2 (en) 1989-03-02
BR8604535A (pt) 1987-07-14
NO169957B (no) 1992-05-18
BG47645A3 (en) 1990-08-15
KR870700005A (ko) 1987-02-28

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