Pyrethrinoid esters derived from isoxazolic or isothiazolic alco

Details Pyrethrinoid esters derived from isoxazolic or isothiazolic alco Pyrethrinoid esters derived from isoxazolic or isothiazolic alco

1993-10-07

1995-07-18

Gerstl, Robert

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

514372, 548214, 548247, C07D26108, A01N 4380

Patent

active

054341752

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/FR93/00119 filed Feb. 5, 1993.
The present invention relates to new pyrethrinoid esters derived from isoxazolic or isothiazolic alcohol, their preparation process and their use as pesticides.
A subject of the invention is, in all their possible stereoisomer forms as well as their mixtures, the compounds of formula (I): ##STR2## in which the ##STR3## radical is in position 3 or 5, X represents a hydrogen atom, a cyano radical or a linear or branched, saturated or unsaturated alkyl radical containing up to 4 carbon atoms, C.tbd.N radical, a saturated or unsaturated, linear or branched alkyl radical containing up to 8 carbon atoms optionally substituted by one or more halogen atoms, a etherified or esterified, n representing the number 0, 1, 2, 3 or 4 or a ##STR4## radical, or an NHalk.sub.1 or ##STR5## radical in which alk.sub.1 and alk.sub.2, identical or different, represent an alkyl radical containing up to 8 carbon atoms, ##STR6## in which: Z.sub.1 and Z.sub.2 each represent a methyl radical, ##STR7## in which Z.sub.3 represents a hydrogen or halogen atom and T.sub.1 and T.sub.2, identical or different, represent a hydrogen atom, a halogen atom, a saturated or unsaturated alkyloxy or alkyl radical containing 1 to 8 carbon atoms optionally substituted by halogens, a mono-, di- or trifluoromethyl or cyano radical or a phenyl nucleus optionally substituted by a halogen, or T.sub.1 and T.sub.2 form together a cycloalkyl radical containing 3 to 6 carbon atoms or a radical: ##STR8## in which B represents an oxygen or sulphur atom; or Z.sub.2 represents a radical: ##STR9## in which a, b, c and d, identical or different, each represent a halogen atom, ##STR10## in which D represents a hydrogen or halogen atom, an alkyloxy radical containing 1 to 8 carbon atoms, G represents an oxygen or sulphur atom and J represents either a saturated or unsaturated, linear, branched or cyclic alkyl radical containing 1 to 8 carbon atoms, optionally substituted by one or more identical or different functional groups, or an aryl group containing 6 to 14 carbon atoms, optionally substituted by one or more identical or different functional groups, or a heterocyclic radical optionally substituted by one or more identical or difference functional groups, or R represents a radical: ##STR11## in which U, in any position on the benzene nucleus, represents a halogen atom, an alkyl radical containing 1 to 8 carbon atoms or an alkoxy radical containing 1 to 8 carbon atoms, m representing the number 0, 1 or 2 and when m is 2, the U substituents can be identical or different.
When X represents an alkyl radical, it is preferably a methyl, ethyl or ethynyl radical.
When Y represents an alkyl radical, it is preferably one of the following radicals: methyl, ethyl, isopropyl, n-butyl, isobutyl, terbutyl, vinyl, allyl, ethynyl or propynyl.
When Y is substituted by a halogen atom, the halogen is preferably fluorine or chlorine, it can be for example the CF.sub.3, CHF.sub.2, CHCl.sub.2, CH.sub.2 F radical or also the ##STR12##
When Y represents an O-alkyl radical, the alkyl preferably has one of the values indicated above.
When Y represents a free, etherified or esterified --(CH.sub.2).sub.n OH radical, it is preferably the --CH.sub.2 OH, --CH.sub.2 OCH.sub.3 or --CH.sub.2 OCOCH.sub.3 radical.
When T.sub.1, T.sub.2 or Z.sub.3 represents a halogen atom, it is preferably a fluorine, chlorine or bromine atom.
When T.sub.1 or T.sub.2 represents an alkyl or alkyloxy radical, it is preferably a methyl, ethyl, propyl, methoxy, ethoxy or propoxy radical.
a, b, c and d preferably represent a chlorine or bromine atom.
When D represents a halogen atom, it is preferably a fluorine, chlorine or bromine atom.
When J represents an alkyl radical substituted by one or more functional groups, by alkyl is preferably meant a radical containing 1 to 8 carbon atoms such as, for example, the methyl, ethyl, propyl, isopropyl, butyl, isobutyl or tert-butyl radical and by functional group is meant one of those mentioned in the European Applic

REFERENCES:
patent: 4833163 (1989-05-01), Martel
Lel, Pestic Sci 7, 288, (1976).

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