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GB1448228A - Substituted 2,2-dimethyl cyclopropane carboxylic acid esters processes for their preparation and their use as insecticides - Google Patents

Substituted 2,2-dimethyl cyclopropane carboxylic acid esters processes for their preparation and their use as insecticides

Info

Publication number
GB1448228A
GB1448228A GB2631674A GB2631674A GB1448228A GB 1448228 A GB1448228 A GB 1448228A GB 2631674 A GB2631674 A GB 2631674A GB 2631674 A GB2631674 A GB 2631674A GB 1448228 A GB1448228 A GB 1448228A
Authority
GB
United Kingdom
Prior art keywords
formula
cyclopropane ring
phenoxybenzyl
compounds
configuration
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
GB2631674A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
NAT RES DEV
National Research Development Corp UK
Original Assignee
NAT RES DEV
National Research Development Corp UK
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
Application filed by NAT RES DEV, National Research Development Corp UK filed Critical NAT RES DEV
Priority to GB2631674A priority Critical patent/GB1448228A/en
Priority to AU72249/74A priority patent/AU484820B2/en
Priority to CH1103774A priority patent/CH608941A5/en
Priority to IL45462A priority patent/IL45462A/en
Priority to CH1465277A priority patent/CH611593A5/en
Priority to IT2628474A priority patent/IT1048189B/en
Priority to DE19742439177 priority patent/DE2439177C2/en
Priority to IE169474A priority patent/IE41614B1/en
Priority to CA206,882A priority patent/CA1045632A/en
Priority to US05/497,056 priority patent/US4024163A/en
Priority to NL7410838A priority patent/NL178590C/en
Priority to FR7428098A priority patent/FR2240914A2/en
Priority to CY99474A priority patent/CY994A/en
Publication of GB1448228A publication Critical patent/GB1448228A/en
Priority to KE291879A priority patent/KE2918A/en
Priority to MY7900141A priority patent/MY7900141A/en
Priority to US06/612,807 priority patent/US4622337A/en
Expired legal-status Critical Current

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

Landscapes

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

Abstract

1448228 3 - Substituted - 2,2 - dimethylcyclopropane - carboxylic acid esters NATIONAL RESEARCH DEVELOPMENT CORP 22 Oct 1974 [22 Oct 1973 13 June 1974] 49098/73 and 26316/74 Addition to 1413491 Heading C2C The invention comprises compounds having the general formula in the form of a substantially pure optical isomer with respect to the cyclopropane ring and having [R] configuration at the carbon atom of the cyclopropane ring carrying the COOR group and wherein (1) the compound is a crystalline isomer wherein R<SP>2</SP> and R<SP>3</SP> are each bromine and R is alpha-cyano-3-phenoxybenzyl, or (2) R<SP>2</SP> and R<SP>3</SP> are each fluorine and R is 3-phenoxybenzyl, alpha-cyano-3-phenoxybenzyl or 5-benzyl-3-furylmethyl, or (3) R<SP>2</SP> and are each chlorine and R is 3-phenoxybenyzl when the cyclopropane ring has [IR, cis or [IR, trans] configuration or R is 5-benzyl-3- furylmethyl when the cyclopropane ring has [IR, cis] configuration. Compounds of Formula I wherein R<SP>2</SP> and R<SP>3</SP> are each chlorine or each fluorine may be prepared by reacting a compound of the formula with a compound of the formula RQ where Q and Q<SP>1</SP> are groups which react together to form an ester linkage, the resolution into the desired configuration on the cyclopropane ring taking place before or after formation of the ester linkage. Compounds of Formula I wherein R<SP>2</SP> and R<SP>3</SP> are each bromine are prepared by dissolving (Œ)-alpha-cyano-3-phenoxybenzyl [IR, cis] 2,2 - dimethyl - 3 - (2,2 - dibromovinyl)- cyclopropane carboxylate in a solvent at elevated temperature and cooling the solution to precipitate the crystalline isomer. The compounds of the invention may be used as active ingredients in insecticidal compositions.
GB2631674A 1972-05-25 1974-06-13 Substituted 2,2-dimethyl cyclopropane carboxylic acid esters processes for their preparation and their use as insecticides Expired GB1448228A (en)

Priority Applications (16)

Application Number Priority Date Filing Date Title
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
AU72249/74A AU484820B2 (en) 1973-08-15 1974-08-12 Improvements relating to insecticides
IE169474A IE41614B1 (en) 1973-08-15 1974-08-13 Substituted 2,2-dimethyl cylopropane carboxylic acid estersprocess for their preperation and their use as insecticides
US05/497,056 US4024163A (en) 1972-05-25 1974-08-13 Insecticides
CH1465277A CH611593A5 (en) 1973-08-15 1974-08-13 Process for the preparation of a cyclopropanecarboxylic acid ester
IT2628474A IT1048189B (en) 1973-08-15 1974-08-13 REFECTIONS RELATED TO INSECTICIDES
DE19742439177 DE2439177C2 (en) 1973-08-15 1974-08-13 (±) -? -Cyan-3-phenoxybenzyl- (1R, trans) - and (1R, cis) -2,2-dimethyl-3- (2,2-dibromovinyl) -cyclopropanecarboxylate and (S) -? -Cyan-3-phenoxybenzyl- (1R, cis) -2,2-dimethyl-3- (2,2-dibromovinyl) -cyclopropanecarboxylate, process for the preparation of the (S) -isomer and insecticides containing these compounds
CH1103774A CH608941A5 (en) 1973-08-15 1974-08-13 Use of a synthetic pyrethroid as insecticide
CA206,882A CA1045632A (en) 1973-08-15 1974-08-13 Insecticides
IL45462A IL45462A (en) 1973-05-24 1974-08-13 (1r)-2,2-dimethyl-3-(2,2-dhialovinyl)-cyclopropanecarboxylic acid ester their preparation and insecticidal compositions containing the ester
NL7410838A NL178590C (en) 1973-08-15 1974-08-13 METHOD FOR PREPARING AN INSECTICIDE PREPARATION; PROCESS FOR PREPARING A SYNTHETIC PYRETHROID.
FR7428098A FR2240914A2 (en) 1973-08-15 1974-08-13 Insecticidal stereoisomeric esters - of 2,2-dimethyl-3-(2,2-di-halovinyl) cyclopropane carboxylic acid which are very toxic to houseflies
CY99474A CY994A (en) 1973-10-22 1974-10-22 Substituted 2,2-dimethyl cyclopropane carboxylic acid esters processes for their preparation and their use as insecticides
KE291879A KE2918A (en) 1973-10-22 1979-02-07 Substituted 2,2-dimethyl cyclopropane carboxylic acid esters, processes for their preparation and their use as insecticides
MY7900141A MY7900141A (en) 1973-10-22 1979-12-31 Substituted 2,2-dimethyl cyclopropane carboxylic acid esters, processes for their preparation and their use as insecticides
US06/612,807 US4622337A (en) 1972-05-25 1984-05-22 2,2-dimethyl-3-(2-halovinyl)cyclopropane carboxlic acid ester pesticides

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
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
GB1448228A true GB1448228A (en) 1976-09-02

Family

ID=26258188

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2631674A Expired GB1448228A (en) 1972-05-25 1974-06-13 Substituted 2,2-dimethyl cyclopropane carboxylic acid esters processes for their preparation and their use as insecticides

Country Status (4)

Country Link
CY (1) CY994A (en)
GB (1) GB1448228A (en)
KE (1) KE2918A (en)
MY (1) MY7900141A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4312816A (en) 1977-07-07 1982-01-26 Sumitomo Chemical Company, Limited Process for preparing optically active α-cyano-3-phenoxybenzyl 2-(4-chlorophenyl)isovalerate
US4341760A (en) 1976-12-24 1982-07-27 Burroughs Wellcome Co. Synergistic compositions
US4683089A (en) * 1978-10-27 1987-07-28 Imperial Chemical Industries Limited Cyclopropane carboxylic acid derivatives
US4897386A (en) * 1976-12-24 1990-01-30 Burroughs Wellcome Co. Synergistic compositions
US5096895A (en) * 1976-12-24 1992-03-17 Burroughs Wellcome Co. Novel synergistic compositions

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4341760A (en) 1976-12-24 1982-07-27 Burroughs Wellcome Co. Synergistic compositions
US4780459A (en) * 1976-12-24 1988-10-25 Burroughs Wellcome Company Synergistic compositions
US4897386A (en) * 1976-12-24 1990-01-30 Burroughs Wellcome Co. Synergistic compositions
US5096895A (en) * 1976-12-24 1992-03-17 Burroughs Wellcome Co. Novel synergistic compositions
US5134132A (en) * 1976-12-24 1992-07-28 Matthewson Michael D Synergistic compounds
US4312816A (en) 1977-07-07 1982-01-26 Sumitomo Chemical Company, Limited Process for preparing optically active α-cyano-3-phenoxybenzyl 2-(4-chlorophenyl)isovalerate
US4683089A (en) * 1978-10-27 1987-07-28 Imperial Chemical Industries Limited Cyclopropane carboxylic acid derivatives
US4780252A (en) * 1978-10-27 1988-10-25 Imperial Chemical Industries Plc Process for separating optical isomers of cyclopropane carboxylic acids

Also Published As

Publication number Publication date
CY994A (en) 1979-08-02
MY7900141A (en) 1979-12-31
KE2918A (en) 1979-03-30

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Legal Events

Date Code Title Description
PS Patent sealed
429A Application made for amendment of specification (sect. 29/1949)
429H Application (made) for amendment of specification now open to opposition (sect. 29/1949)
429D Case decided by the comptroller ** specification amended (sect. 29/1949)
SPA Amended specification published