GB1448228A

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

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
1973-10-22
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.)

National Research Development Corp UK

Original Assignee
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.)
1973-10-22
Filing date
1974-06-13
Publication date
1976-09-02

1974-06-13
Application filed by National Research Development Corp UK
filed
Critical
National Research Development Corp UK

1974-06-13
Priority to GB2631674A
priority
Critical
patent/GB1448228A/en

1974-08-12
Priority to AU72249/74A
priority
patent/AU484820B2/en

1974-08-13
Priority to CH1465277A
priority
patent/CH611593A5/en

1974-08-13
Priority to US05/497,056
priority
patent/US4024163A/en

1974-08-13
Priority to CH1103774A
priority
patent/CH608941A5/en

1974-08-13
Priority to DE19742439177
priority
patent/DE2439177C2/en

1974-08-13
Priority to IT2628474A
priority
patent/IT1048189B/en

1974-08-13
Priority to IL45462A
priority
patent/IL45462A/en

1974-08-13
Priority to FR7428098A
priority
patent/FR2240914A2/en

1974-08-13
Priority to CA206,882A
priority
patent/CA1045632A/en

1974-08-13
Priority to NL7410838A
priority
patent/NL178590C/en

1974-08-13
Priority to IE169474A
priority
patent/IE41614B1/en

1974-10-22
Priority to CY99474A
priority
patent/CY994A/en

1976-09-02
Publication of GB1448228A
publication
Critical
patent/GB1448228A/en

1979-02-07
Priority to KE291879A
priority
patent/KE2918A/en

1979-12-31
Priority to MY7900141A
priority
patent/MY7900141A/en

1984-05-22
Priority to US06/612,807
priority
patent/US4622337A/en

Status
Expired
legal-status
Critical
Current

Links

Espacenet

Global Dossier

Discuss

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

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 R2 and R3 are each bromine and R is alpha-cyano-3-phenoxybenzyl, or (2) R2 and R3 are each fluorine and R is 3-phenoxybenzyl, alpha-cyano-3-phenoxybenzyl or 5-benzyl-3-furylmethyl, or (3) R2 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 R2 and R3 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 Q1 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 R2 and R3 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

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

CA206,882A

CA1045632A
(en)

1973-08-15
1974-08-13
Insecticides

CH1103774A

CH608941A5
(en)

1973-08-15
1974-08-13
Use of a synthetic pyrethroid as insecticide

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

IT2628474A

IT1048189B
(en)

1973-08-15
1974-08-13

REFECTIONS RELATED TO INSECTICIDES

CH1465277A

CH611593A5
(en)

1973-08-15
1974-08-13
Process for the preparation of a cyclopropanecarboxylic acid ester

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

US05/497,056

US4024163A
(en)

1972-05-25
1974-08-13
Insecticides

NL7410838A

NL178590C
(en)

1973-08-15
1974-08-13

METHOD FOR PREPARING AN INSECTICIDE PREPARATION; PROCESS FOR PREPARING A SYNTHETIC PYRETHROID.

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

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 (4)

* 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

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

1974

1974-06-13
GB
GB2631674A
patent/GB1448228A/en
not_active
Expired

1974-10-22
CY
CY99474A
patent/CY994A/en
unknown

1979

1979-02-07
KE
KE291879A
patent/KE2918A/en
unknown

1979-12-31
MY
MY7900141A
patent/MY7900141A/en
unknown

Cited By (7)

* 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

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

MY7900141A
(en)

1979-12-31

KE2918A
(en)

1979-03-30

CY994A
(en)

1979-08-02

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Substituted 2, 2-dimethyl cyclopropane carboxylic acid¹esters.

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JPS54130536A
(en)

1979-10-09

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Legal Events

Date
Code
Title
Description

1977-01-13
PS
Patent sealed

1978-02-15
429A
Application made for amendment of specification (sect. 29/1949)

1978-02-22
429H
Application (made) for amendment of specification now open to opposition (sect. 29/1949)

1978-07-05
429D
Case decided by the comptroller ** specification amended (sect. 29/1949)

1978-07-12
SPA
Amended specification published

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