CH611593A5 - Process for the preparation of a cyclopropanecarboxylic acid ester - Google Patents

Process for the preparation of a cyclopropanecarboxylic acid ester

Info

Publication number
CH611593A5
CH611593A5 CH1465277A CH1465277A CH611593A5 CH 611593 A5 CH611593 A5 CH 611593A5 CH 1465277 A CH1465277 A CH 1465277A CH 1465277 A CH1465277 A CH 1465277A CH 611593 A5 CH611593 A5 CH 611593A5
Authority
CH
Switzerland
Prior art keywords
residue
preparation
acid ester
cyclopropanecarboxylic acid
phenoxybenzyl
Prior art date
Application number
CH1465277A
Inventor
Michael Elliott
Norman Frank Janes
David Allen Pulman
Original Assignee
Nat Res Dev
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 GB2631674A external-priority patent/GB1448228A/en
Application filed by Nat Res Dev filed Critical Nat Res Dev
Publication of CH611593A5 publication Critical patent/CH611593A5/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/42—Singly bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The compounds of formula IIA below in the form of an optical isomer having the (R) configuration at C1 of the ring of the cyclopropane are obtained from a derivative of the cyclopropane containing the acyl residue of formula IIB below. R<2> and R<3> represent F, Cl or Br and R represents 3-phenoxybenzyl, alpha -cyano-3-phenoxybenzyl or 5-benzyl-3-furylmethyl. The process consists in introducing the residue R by esterification and in introducing the dihalovinyl residue in position 3 by the Wittig reaction using triphenylphosphine and a carbon tetrahalide. The compounds of formula IIA are particularly effective insecticides. <IMAGE>
CH1465277A 1973-08-15 1974-08-13 Process for the preparation of a cyclopropanecarboxylic acid ester CH611593A5 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB3953973 1973-08-15
GB4909873 1973-10-22
GB2631674A GB1448228A (en) 1973-10-22 1974-06-13 Substituted 2,2-dimethyl cyclopropane carboxylic acid esters processes for their preparation and their use as insecticides

Publications (1)

Publication Number Publication Date
CH611593A5 true CH611593A5 (en) 1979-06-15

Family

ID=27258509

Family Applications (2)

Application Number Title Priority Date Filing Date
CH1103774A CH608941A5 (en) 1973-08-15 1974-08-13 Use of a synthetic pyrethroid as insecticide
CH1465277A CH611593A5 (en) 1973-08-15 1974-08-13 Process for the preparation of a cyclopropanecarboxylic acid ester

Family Applications Before (1)

Application Number Title Priority Date Filing Date
CH1103774A CH608941A5 (en) 1973-08-15 1974-08-13 Use of a synthetic pyrethroid as insecticide

Country Status (7)

Country Link
CA (1) CA1045632A (en)
CH (2) CH608941A5 (en)
DE (1) DE2439177C2 (en)
FR (1) FR2240914A2 (en)
IE (1) IE41614B1 (en)
IT (1) IT1048189B (en)
NL (1) NL178590C (en)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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)
NZ184241A (en) * 1976-06-16 1979-12-11 Ici Ltd A process for the preparation of certain cyano-substituted ester -cyano-3-phenoxybenzyl 3-(2,2-dichl-orovinyl)-2,2-dimethyl-cyclopropane carboxylate insecticidal composition
FR2396006A1 (en) * 1977-06-27 1979-01-26 Roussel Uclaf NEW CYCLOPROPANIC CORE COMPOUNDS, PREPARATION PROCESS AND APPLICATION TO THE PREPARATION OF CYCLOPROPANIC DERIVATIVES WITH DIHALOVINYL CHAIN
CA1123452A (en) * 1977-06-30 1982-05-11 John H. Davies Cyclopropyl carboxylate compounds a process for their manufacture and their use as pesticides
CA1215717A (en) * 1977-09-26 1986-12-23 Samuel B. Soloway Process for converting a stereoisomeric ester into its diastereoisomer
DE2860760D1 (en) * 1977-11-22 1981-09-17 Shell Int Research Method of controlling acarid pests by means of cyclopropane carboxylate esters, the use of such esters as an acaricide, and one of said esters as a novel compound
DE2800922A1 (en) 1978-01-10 1979-07-19 Bayer Ag PROCESS FOR THE SEPARATION OF STEREOISOMER VINYLCYCLOPROPANIC CARBONIC ACIDS
ZA7911B (en) * 1978-01-31 1980-01-30 Roussel Uclaf Optically-active substituted benzyl alcohol and process for preparing it
MD244C2 (en) * 1978-01-31 1995-12-31 Roussel Uclaf, Societe Anonyme Method of preparation of ester of alcohol (S)-a-cyai-3-fenoxybenzol and 1R, cis-2,2-domethyl-3-(2'2'-dibromvinil)-cyclopropan-1-carbonic acid
JPS54163811A (en) * 1978-05-30 1979-12-26 Wellcome Found Harmful organism controlling composition
DK158037C (en) * 1978-06-02 1990-08-13 Shell Int Research METHOD OF COMBATING ACARI USING OXYIMINO-SUBSTITUTED CYCLOPROPANCARBOXYL ACID ESTERS AND Z-ISOMERS OF CERTAIN THESE ESTERS FOR USE BY THE PROCEDURE
FR2428029A1 (en) * 1978-06-06 1980-01-04 Roussel Uclaf ESTERS OF CYCLOPROPANE CARBOXYLIC ACIDS SUBSTITUTED BY A-CYANE ALCOHOL, PROCESS FOR THEIR PREPARATION AND INSECTICIDE OR NEMATICIDE COMPOSITIONS CONTAINING THEM
FR2455024A1 (en) * 1979-04-03 1980-11-21 Roussel Uclaf NEW PROCESS FOR THE SPLITTING OF ACIDS D, L-CIS 2,2-DIMETHYL 3- (2 ', 2'-DIHALOVINYL) CYCLOPROPANE-1-CARBOXYLIC
US4261921A (en) * 1979-06-06 1981-04-14 Fmc Corporation Process for preparation of a crystalline insecticidal pyrethroid enantiomer pair
HU198373B (en) * 1986-01-08 1989-10-30 Chinoin Gyogyszer Es Vegyeszet Artropodicide composition containing trans-cipermetrin isomeres and process for producing the active components
CA1301642C (en) * 1987-03-30 1992-05-26 Howard Bernard Dawson Chemical formulations
CN1157358C (en) * 2000-01-12 2004-07-14 住友化学工业株式会社 Process for synthetizing 2,2-demethyl-3-(1-propenyl) cyclopropane carboxylic ester
WO2022200364A1 (en) 2021-03-25 2022-09-29 Syngenta Crop Protection Ag Insect, acarina and nematode pest control
EP4337015A1 (en) 2021-05-14 2024-03-20 Syngenta Crop Protection AG Insect, acarina and nematode pest control
WO2022268813A1 (en) 2021-06-24 2022-12-29 Syngenta Crop Protection Ag Insect, acarina and nematode pest control
WO2022268815A1 (en) 2021-06-24 2022-12-29 Syngenta Crop Protection Ag Insect, acarina and nematode pest control
WO2023105064A1 (en) 2021-12-10 2023-06-15 Syngenta Crop Protection Ag Insect, acarina and nematode pest control
WO2023105065A1 (en) 2021-12-10 2023-06-15 Syngenta Crop Protection Ag Insect, acarina and nematode pest control

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5237046B1 (en) * 1969-11-14 1977-09-20

Also Published As

Publication number Publication date
IE41614L (en) 1975-02-15
FR2240914A2 (en) 1975-03-14
DE2439177A1 (en) 1975-02-27
IE41614B1 (en) 1980-02-13
NL7410838A (en) 1975-02-18
DE2439177C2 (en) 1984-02-02
AU7224974A (en) 1976-02-12
NL178590B (en) 1985-11-18
CH608941A5 (en) 1979-02-15
FR2240914B2 (en) 1982-03-19
NL178590C (en) 1986-04-16
CA1045632A (en) 1979-01-02
IT1048189B (en) 1980-11-20

Similar Documents

Publication Publication Date Title
CH611593A5 (en) Process for the preparation of a cyclopropanecarboxylic acid ester
ES462473A1 (en) Polyhalogenated carboxylic acids
IE37681B1 (en) Improvements relating to insecticides
ES2008658B3 (en) PROCEDURE FOR THE PREPARATION OF MONOSTERS OR DIESTERS OF ENDOETHANE ACID 9,10 DIHIDRO ANTRACENO DICARBOXILICO-11,11, NEW MONOSTERS OR DIESTERS SO PREPARED AND THEIR USE FOR THE PREPARATION OF ASYMETHYL-METHYLENE AND MALONATES.
GB1512419A (en) esters and a process for their conversion to trans-2,2-di2,2-dimethyl-3,5,5,5-tetrachloro-pentane-1-carboxylic acidmethyl-3-(2,2-dichlorovinyl)-cyclopropane-1-carboxylic acid and esters thereof
IL54665A (en) Preparation for substituted benzyl esters of 2,2-dimethyl-3-(2,2-disubstituted vinyl)cyclopropane carboxylic acids and insecticical compsitions containing them
EP0022970A3 (en) Stereoisomers of alpha-cyano-3-phenoxy-4-fluor-benzyl esters of 2,2-dimethyl-3-(2,2-dichloro-vinyl)-cyclopropane carboxylic acid, process for their preparation and their application as insecticides and acaricides, and their intermediates
GB2016447A (en) Cyclopropane carboxylic acid esters containing a polyhalogenated substituent
IE802442L (en) Cyclopropane carboxylic acids esters
AU8143487A (en) New derivatives of 2,2-dimethyl cyclopropane carboxylic acid having a saturated halogenated chain in position 3, the process and the intermediates for their preparation, their use as pesticides and the compositions containing them
ES474682A1 (en) Phenoxy-alpha-vinylbenzyl esters of cyclopropane carboxylic acids, process for their preparation and their use as pesticides.
SE8102525L (en) PROCEDURE FOR PREPARING CYCLOPROPANCARBOXYL ACID ESTER DERIVATIVES
DE3062046D1 (en) (+/-)-(alpha-cyano-3-phenoxy-4-fluoro-benzylic)esters of (+/-)-trans-3-(e,z-2-chloro-2-(4-chloro-phenyl)-vinyl)-2,2-dimethyl-cyclopropane carboxylic acid, their e and z isomers, a process for their preparation and their application as ectoparasiticides
EP0121847A3 (en) 2,2-dimethyl-3-(2-halovinyl)cyclopropane carboxylates, process for their preparation and their use as pesticides
MX9303331A (en) PROCEDURE FOR PREPARING ESTERS OF ACID 2,2-DIMETHYL-3 - ((Z) -1-PROPENYL) -CYCLOPROPAN CARBOXYLIC AND INTERMEDIATE COMPOUNDS.
JPS547236A (en) High-resolution cathode-ray tube
JPS5612355A (en) Manufacture of optically active alphaacyanoalcohol
GB1556999A (en) Unsaturated carboxylic acids
SE8102526L (en) PROCEDURE FOR PREPARING CYCLOPROPANCARBOXYL ACID ESTER DERIVATIVES
GB1448228A (en) Substituted 2,2-dimethyl cyclopropane carboxylic acid esters processes for their preparation and their use as insecticides
GB2026483A (en) Cyclopropane derivatives
DE3173145D1 (en) Cyclopropane derivatives, processes for their preparation and their use in the preparation of dihalovinylcyclopropane carboxylic acids
JPS5281396A (en) Preparation of curable resins
JPS5639043A (en) Cyclopropanecarboxylic acid ester and insecticide and miticide
JPS52116440A (en) Preparation of vinylcyclopropane carboxylic acid ester

Legal Events

Date Code Title Description
PUE Assignment

Owner name: BRITISH TECHNOLOGY GROUP LTD

PL Patent ceased