FR2351943A1 - 2-(Dihalovinyl) cyclopropane carboxylate insecticides prodn. - by reacting alkenol and orthoformate, addition of carbon tetrahalide, basic cyclisation and dehydrohalogenation - Google Patents

2-(Dihalovinyl) cyclopropane carboxylate insecticides prodn. - by reacting alkenol and orthoformate, addition of carbon tetrahalide, basic cyclisation and dehydrohalogenation

Info

Publication number
FR2351943A1
FR2351943A1 FR7639508A FR7639508A FR2351943A1 FR 2351943 A1 FR2351943 A1 FR 2351943A1 FR 7639508 A FR7639508 A FR 7639508A FR 7639508 A FR7639508 A FR 7639508A FR 2351943 A1 FR2351943 A1 FR 2351943A1
Authority
FR
France
Prior art keywords
lower alkyl
insecticides
reacting
addition
dihalovinyl
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
FR7639508A
Other languages
French (fr)
Other versions
FR2351943B1 (en
Inventor
Kiyoshi Kondo
Kiyohide Matsui
Akira Negishi
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.)
Sagami Chemical Research Institute
Original Assignee
Sagami Chemical Research Institute
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 JP13663174A external-priority patent/JPS5165734A/en
Priority claimed from JP50028606A external-priority patent/JPS5817451B2/en
Application filed by Sagami Chemical Research Institute filed Critical Sagami Chemical Research Institute
Publication of FR2351943A1 publication Critical patent/FR2351943A1/en
Application granted granted Critical
Publication of FR2351943B1 publication Critical patent/FR2351943B1/fr
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/32—Compounds having groups or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
    • C07C43/14—Unsaturated ethers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/27—Preparation of carboxylic acid esters from ortho-esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/317—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/62—Halogen-containing esters
    • C07C69/65—Halogen-containing esters of unsaturated acids

Landscapes

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

Abstract

Cyclopropanecarboxylates of formula (I), are prepd. by reacting alkenols (II) with orthoesters (III) to give unsatd. esters, (IV), which, opt. after transesterification to (V), are subjected to CX4 addition to give (VI) and these dehydrohalogenated with base. (R is R1 or R8; R1 is lower alkyl; R2 and R3 are H, lower alkyl or cycloalkyl, phenyl or aralkyl; or R2 and R3 are together 2C alkylene or where one of them is not H the other can be lower alkoxycarbonyl or alkanoyl, aroyl, di (lower alkyl)amido or CN; R7 is H, lower alkyl ro cycloalkyl, phenyl or aralkyl; R8 is a gp. of formula (VII) R9 is H or CN; R10 is H, lower alkyl, phenoxy, benzyl or phenylmercapto; R11 is H or lower alkyl; R12 is O, S or vinylene; X is halo). The final stage proceeds via intermediates X, Y and Z which give (I) on further loss of HX (I) have insecticides and are prepd. more easily and in higher yields than by known processes. The prod. contain 50-90% of the more active trans isomers. Specif. claimed are (I) where X is Cl, R2 and R3 are CH3 and R is ethyl or 3-phenoxybenzyl.
FR7639508A 1974-11-30 1976-12-29 2-(Dihalovinyl) cyclopropane carboxylate insecticides prodn. - by reacting alkenol and orthoformate, addition of carbon tetrahalide, basic cyclisation and dehydrohalogenation Granted FR2351943A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP13663174A JPS5165734A (en) 1974-11-30 1974-11-30 SHIKUROPUROPANKARUBONSANESUTERUO SEIZOSURU HOHO
JP50028606A JPS5817451B2 (en) 1975-03-11 1975-03-11 Production method of γ↓-chloro↓-δ↓-unsaturated carboxylic acid ester

Publications (2)

Publication Number Publication Date
FR2351943A1 true FR2351943A1 (en) 1977-12-16
FR2351943B1 FR2351943B1 (en) 1979-07-20

Family

ID=26366748

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7639508A Granted FR2351943A1 (en) 1974-11-30 1976-12-29 2-(Dihalovinyl) cyclopropane carboxylate insecticides prodn. - by reacting alkenol and orthoformate, addition of carbon tetrahalide, basic cyclisation and dehydrohalogenation

Country Status (1)

Country Link
FR (1) FR2351943A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2341553A1 (en) * 1976-02-19 1977-09-16 Bayer Ag PROCESS FOR THE PRODUCTION OF 2,2-DIMETHYL-3- (2 ', 2'-DICHLOROVINYL) -CYCLOPROPANE-1-CARBOXYLIC ACID

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2341553A1 (en) * 1976-02-19 1977-09-16 Bayer Ag PROCESS FOR THE PRODUCTION OF 2,2-DIMETHYL-3- (2 ', 2'-DICHLOROVINYL) -CYCLOPROPANE-1-CARBOXYLIC ACID

Also Published As

Publication number Publication date
FR2351943B1 (en) 1979-07-20

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