FR2424249A1 - Insecticidal ester(s) of alpha-halogenated alcohol(s) - useful in prepn. of insecticidal corresp. cyano-ester(s) - Google Patents

Insecticidal ester(s) of alpha-halogenated alcohol(s) - useful in prepn. of insecticidal corresp. cyano-ester(s)

Info

Publication number
FR2424249A1
FR2424249A1 FR7732414A FR7732414A FR2424249A1 FR 2424249 A1 FR2424249 A1 FR 2424249A1 FR 7732414 A FR7732414 A FR 7732414A FR 7732414 A FR7732414 A FR 7732414A FR 2424249 A1 FR2424249 A1 FR 2424249A1
Authority
FR
France
Prior art keywords
ester
insecticidal
prepn
iiia
formula
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.)
Granted
Application number
FR7732414A
Other languages
French (fr)
Other versions
FR2424249B1 (en
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.)
Sanofi Aventis France
Original Assignee
Roussel Uclaf SA
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 Roussel Uclaf SA filed Critical Roussel Uclaf SA
Priority to FR7732414A priority Critical patent/FR2424249A1/en
Priority to US05/951,184 priority patent/US4277617A/en
Priority to DE7878400142T priority patent/DE2861367D1/en
Priority to AT0756778A priority patent/AT366022B/en
Priority to EP78400142A priority patent/EP0001944B1/en
Priority to JP13009278A priority patent/JPS5470242A/en
Priority to BR7807025A priority patent/BR7807025A/en
Priority to IT51658/78A priority patent/IT1106074B/en
Priority to DK475878A priority patent/DK475878A/en
Priority to PT68708A priority patent/PT68708A/en
Priority to ES474545A priority patent/ES474545A1/en
Priority to IE2126/78A priority patent/IE47961B1/en
Priority to AU41072/78A priority patent/AU518964B2/en
Priority to CA000314610A priority patent/CA1181411A/en
Priority to HU78RO998A priority patent/HU182569B/en
Publication of FR2424249A1 publication Critical patent/FR2424249A1/en
Priority to US06/193,798 priority patent/US4315868A/en
Priority to AT0573080A priority patent/AT367732B/en
Application granted granted Critical
Publication of FR2424249B1 publication Critical patent/FR2424249B1/fr
Priority to JP62074579A priority patent/JPS62265257A/en
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Furan Compounds (AREA)
  • Indole Compounds (AREA)

Abstract

Intermediate priorities: 27.10.77, 24.7.78-FR-032415, 021811. D/S: E(BE, CH, DT, GB, LU, NL). (A) Cpds. of formula (I) as stereoisomers and mixts. thereof, are new: (where X is F, Cl or Br; R1 is of formula (IIa) or (IIb) where Y1=Y2=CH3 or Y1 is H and Y2 is of formula (IIIa) or (IIIb) Y3 and Y4 are each F, Cl or Br or are each H or CH3; when Y2 is (IIIb), then (IIa) corresponds to a racemic or optically active cis or trans acid residue or mixt. of cis acid and trans acid residues; Z is H, F, Cl, Br or 1-4C opt. branched alkyl or alkoxy, (IIb) corresponding to an optically active or racemic acid residue; R2, when Y2 is not (IIIa), is (IVa-e) where A is O-Ph, -O-m-tolyl, -O-CH=CCl2, -S-Ph or R2, when Y2 is (IIIa), is m-phenoxyphenyl; the existence of the asymmetric C atom substd. by X giving 2 diastereoisomers (A and B) for the ester obtd. with any particular defined acid stereoisomer). (B) Also new is the prepn. of cpds. (V) by reaction of (I) with a cpd. generating CN- ions, partic. an alkali cyanide, pref. in acetonitrile or DMF as solvent: (I) are insecticides for domestic and agricultural use and intermediates to pesticidal, esp. insecticidal esters. (V) include several known high activity insecticides. Prepn. of (V) from (I) gives good yield and avoids the need for using alpha-cyano-3-phenoxybenzyl alcohol which is sensitive and difficult to handle.
FR7732414A 1977-10-27 1977-10-27 Insecticidal ester(s) of alpha-halogenated alcohol(s) - useful in prepn. of insecticidal corresp. cyano-ester(s) Granted FR2424249A1 (en)

Priority Applications (18)

Application Number Priority Date Filing Date Title
FR7732414A FR2424249A1 (en) 1977-10-27 1977-10-27 Insecticidal ester(s) of alpha-halogenated alcohol(s) - useful in prepn. of insecticidal corresp. cyano-ester(s)
US05/951,184 US4277617A (en) 1977-10-27 1978-10-13 Process for the preparation of esters
DE7878400142T DE2861367D1 (en) 1977-10-27 1978-10-20 Esters of alpha-halogenated alcohols, method of preparation and application to the synthesis of esters of alpha-cyano substituted alcohols
AT0756778A AT366022B (en) 1977-10-27 1978-10-20 METHOD FOR PRODUCING NEW CYCLOPROPANE CARBONIC ACID ESTERS
EP78400142A EP0001944B1 (en) 1977-10-27 1978-10-20 Esters of alpha-halogenated alcohols, method of preparation and application to the synthesis of esters of alpha-cyano substituted alcohols
JP13009278A JPS5470242A (en) 1977-10-27 1978-10-24 Ester of alphaahalogenoalcohol*its manufacture and use in synthesis of said ester
BR7807025A BR7807025A (en) 1977-10-27 1978-10-25 PROCESS TO PREPARE, IN ALL ITS STEREO ISOMERS OR IN THE FORM OF STEREO ISOMER MIXTURES, ALPHA-HALOGENATED ALCOHOL ESTERS, ITS APPLICATION, AND PROCESS TO PREPARE IN ALL ITS STEREO ISOMERS OR IN A MONEY FORM -ISOMERS, ALPHA-CYANATED ALCOHOL ESTERS
PT68708A PT68708A (en) 1977-10-27 1978-10-26 PROCESS FOR THE PREPARATION OF ALPHA-HALOGEN ALCOHOL ESTERS AND THE APPLICATION OF SAID ESTERS TO THE SYNTHESIS OF ALPHA-CYAN ALCOHOL ESTERS
IT51658/78A IT1106074B (en) 1977-10-27 1978-10-26 PROCESS FOR THE PRODUCTION OF ALPHA-HALOGENATED ALCOHOL ESTERS PRODUCT OBTAINED AND ITS USE IN THE SYNTHESIS OF ALPHA-CYANALCOAL ESTERS
ES474545A ES474545A1 (en) 1977-10-27 1978-10-26 Esters of alpha-halogenated alcohols, method of preparation and application to the synthesis of esters of alpha-cyano substituted alcohols.
IE2126/78A IE47961B1 (en) 1977-10-27 1978-10-26 Chemical compounds
AU41072/78A AU518964B2 (en) 1977-10-27 1978-10-26 Ester of halogeno alcohols
DK475878A DK475878A (en) 1977-10-27 1978-10-26 ESTERS OF ALFA-HALOGENATED ALCOHOLS AND METHODS OF PREPARATION
CA000314610A CA1181411A (en) 1977-10-27 1978-10-27 ESTERS OF .alpha.-HALOGENATED ALCOHOLS, PROCESS FOR PREPARING THE SAME AND INSECTICIDAL COMPOSITIONS CONTAINING THEM
HU78RO998A HU182569B (en) 1977-10-27 1978-10-27 Process for producing alpha-halogenated and alpha-cyano esters
US06/193,798 US4315868A (en) 1977-10-27 1980-10-03 Process for the preparation of α-cyanobenzyl esters
AT0573080A AT367732B (en) 1977-10-27 1980-11-24 METHOD FOR PRODUCING NEW 2-PHENYL-2-ISOPROPYL ACETIC ESTERS
JP62074579A JPS62265257A (en) 1977-10-27 1987-03-30 Synthesis of alpha-cyanoalcohol ester

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7732414A FR2424249A1 (en) 1977-10-27 1977-10-27 Insecticidal ester(s) of alpha-halogenated alcohol(s) - useful in prepn. of insecticidal corresp. cyano-ester(s)

Publications (2)

Publication Number Publication Date
FR2424249A1 true FR2424249A1 (en) 1979-11-23
FR2424249B1 FR2424249B1 (en) 1982-07-16

Family

ID=9197011

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7732414A Granted FR2424249A1 (en) 1977-10-27 1977-10-27 Insecticidal ester(s) of alpha-halogenated alcohol(s) - useful in prepn. of insecticidal corresp. cyano-ester(s)

Country Status (4)

Country Link
JP (1) JPS62265257A (en)
AT (1) AT366022B (en)
AU (1) AU518964B2 (en)
FR (1) FR2424249A1 (en)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2805226A1 (en) * 1977-02-11 1978-08-17 Ciba Geigy Ag CYCLOPROPANIC CARBON ACID ESTERS, THE PROCESS FOR THEIR MANUFACTURING AND THEIR USE IN PEST CONTROL

Also Published As

Publication number Publication date
AU518964B2 (en) 1981-10-29
AT366022B (en) 1982-03-10
ATA756778A (en) 1981-07-15
AU4107278A (en) 1980-05-01
FR2424249B1 (en) 1982-07-16
JPH0224266B2 (en) 1990-05-29
JPS62265257A (en) 1987-11-18

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