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GB2251621A - Process for the preparation of pyrethroide derivatives - Google Patents

Process for the preparation of pyrethroide derivatives

Info

Publication number
GB2251621A
GB2251621A GB9205920A GB9205920A GB2251621A GB 2251621 A GB2251621 A GB 2251621A GB 9205920 A GB9205920 A GB 9205920A GB 9205920 A GB9205920 A GB 9205920A GB 2251621 A GB2251621 A GB 2251621A
Authority
GB
United Kingdom
Prior art keywords
general formula
cyanhydride
pyrethroide
derivatives
acylated
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
GB9205920A
Other versions
GB9205920D0 (en
GB2251621B (en
Inventor
Sandor Botar
Istvan Szekely
Bela Bertok
Antal Gajary
Gyoergy Hidasi
Sandor Zoltan
Janis Hajimichael
Andras Rapi
Ferenc Lindwurm
Laszlo Csiz
Agnes Hegedues
Istvan Lak
Maria Tary
Peterne Magyar
Lajos Nagy
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.)
Chinoin Private Co Ltd
Original Assignee
Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt
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 Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt filed Critical Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt
Publication of GB9205920D0 publication Critical patent/GB9205920D0/en
Publication of GB2251621A publication Critical patent/GB2251621A/en
Application granted granted Critical
Publication of GB2251621B publication Critical patent/GB2251621B/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/38—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by esterified hydroxy groups
    • C07C255/39—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by esterified hydroxy groups with hydroxy groups esterified by derivatives of 2,2-dimethylcyclopropane carboxylic acids, e.g. of chrysanthemumic acids

Landscapes

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

Abstract

The invention relates to the preparation of pyrethroide derivatives in a great purity suitable for controlled crystallisation. The pyrethroides of general formula (I), wherein A is a chlorine or bromine atom or a methyl group, Y is a hydrogen, a fluor or chlorine atom, the waved line means an R respectively S configuration, are obtained in a reaction in the course of which cyanhydride of general formula (II) is acylated with acid chloride of general formula (III), and the cyanhydride of general formula (II) is prepared from benzaldehyde of general formula (IV) by reacting the same with alkali cyanide and water using an amine as catalyst, characterized by that in the aqueous alkalicyanide solution of 7-9 mol % benzaldehyde is added in the presence of 0,15-0,25 mol equivalents of amine, and the cyanhydride formed in the reaction mixture is acylated in statu nascens parallel to the formation of cyanhydride with an acid chloride, and the cypermetrine emulsion obtained is extracted with an apolar solvent.
GB9205920A 1990-07-27 1992-03-18 Process for the preparation of pyrethroid derivatives Expired - Fee Related GB2251621B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/HU1990/000053 WO1992002492A1 (en) 1990-07-27 1990-07-27 Process for the preparation of pyrethroide derivatives

Publications (3)

Publication Number Publication Date
GB9205920D0 GB9205920D0 (en) 1992-04-29
GB2251621A true GB2251621A (en) 1992-07-15
GB2251621B GB2251621B (en) 1994-04-06

Family

ID=10980904

Family Applications (1)

Application Number Title Priority Date Filing Date
GB9205920A Expired - Fee Related GB2251621B (en) 1990-07-27 1992-03-18 Process for the preparation of pyrethroid derivatives

Country Status (3)

Country Link
GB (1) GB2251621B (en)
HK (1) HK1003993A1 (en)
WO (1) WO1992002492A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
LT4405B (en) 1995-04-24 1998-11-25 Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt. Pesticide formulations and process for the manufacture thereof

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH589051A5 (en) * 1971-06-29 1977-06-30 Sumitomo Chemical Co
EP0039173A1 (en) * 1980-04-21 1981-11-04 Ici Americas Inc. Preparation of cyano substituted benzyl ester insecticides
US4323685A (en) * 1980-06-13 1982-04-06 Fmc Corporation Preparation of esters
US4382894A (en) * 1981-06-22 1983-05-10 Ciba-Geigy Corporation Production of α-cyanobenzyl esters

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CH589051A5 (en) * 1971-06-29 1977-06-30 Sumitomo Chemical Co
EP0039173A1 (en) * 1980-04-21 1981-11-04 Ici Americas Inc. Preparation of cyano substituted benzyl ester insecticides
US4323685A (en) * 1980-06-13 1982-04-06 Fmc Corporation Preparation of esters
US4382894A (en) * 1981-06-22 1983-05-10 Ciba-Geigy Corporation Production of α-cyanobenzyl esters

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
LT4405B (en) 1995-04-24 1998-11-25 Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt. Pesticide formulations and process for the manufacture thereof
US5912267A (en) * 1995-04-24 1999-06-15 Chinoin Pharmaceutical & Chemical Works Co., Ltd. Pesticide formulations and process for the manufacture thereof

Also Published As

Publication number Publication date
GB9205920D0 (en) 1992-04-29
HK1003993A1 (en) 1998-11-13
WO1992002492A1 (en) 1992-02-20
GB2251621B (en) 1994-04-06

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Legal Events

Date Code Title Description
PCNP Patent ceased through non-payment of renewal fee

Effective date: 19990727