CH611593A5 - Process for the preparation of a cyclopropanecarboxylic acid ester - Google Patents
Process for the preparation of a cyclopropanecarboxylic acid esterInfo
- 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
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>
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)
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)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5237046B1 (en) * | 1969-11-14 | 1977-09-20 |
-
1974
- 1974-08-13 NL NL7410838A patent/NL178590C/en active Search and Examination
- 1974-08-13 CH CH1103774A patent/CH608941A5/en not_active IP Right Cessation
- 1974-08-13 CA CA206,882A patent/CA1045632A/en not_active Expired
- 1974-08-13 IT IT2628474A patent/IT1048189B/en active
- 1974-08-13 FR FR7428098A patent/FR2240914A2/en active Granted
- 1974-08-13 IE IE169474A patent/IE41614B1/en unknown
- 1974-08-13 CH CH1465277A patent/CH611593A5/en not_active IP Right Cessation
- 1974-08-13 DE DE19742439177 patent/DE2439177C2/en not_active Expired
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 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUE | Assignment |
Owner name: BRITISH TECHNOLOGY GROUP LTD |
|
PL | Patent ceased |