Insecticidal and acaricidal plant-protection agents containing s

Details Insecticidal and acaricidal plant-protection agents containing s Insecticidal and acaricidal plant-protection agents containing s

1994-01-13

1995-06-27

Gerstl, Robert

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

548131, C07D27106, A01N 4382

Patent

active

054280494

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 PCT/EP92/01525 Jul. 6, 1992.
The present invention relates to the use of 1,2,4-oxadiazole derivatives, some of which are already known, as insecticides and acaricides in plant protection.
It is already known that certain 1,2,4-oxadiazole derivatives possess parasiticidal (in particular endoparasiticidal) activity in humans and animals (cf. U.S. Pat. No. 4,012,377).
Certain 1,2,4-oxadiazole derivatives and their use as endoparasiticides are the subject-matter of an older, but not previously published, patent application (cf. German patent application No. 4041474 of 22.12.1990).
It has now been found that the 1,2,4-oxadiazole derivatives, some of which are already known, of the general formula (I) ##STR2## in which R.sup.1 represents hydrogen, or represents in each case optionally substituted alkyl, cycloalkyl, aryl or heterocyclyl, or represents in each case optionally substituted alkyl, alkoxy or alkylthio, or represents in each case optionally substituted alkyl, alkoxy or alkylthio, and halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio, halogenoalkylthio, alkylsulphinyl, halogenoalkylsulphinyl, alkylsulphonyl, halogenoalkylsulphonyl, alkylamino, dialkylamino, alkylcarbonylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkoxyalkyl, hydroxyalkoxy or alkoxyalkoxy, or represents aryl, aryloxy, aralkyloxy, arylthio, aralkylthio, arylsulphinyl or arylsulphonyl, which are in each case optionally substituted by halogen, alkyl, halogenoalkyl, alkoxy or halogenoalkoxy, or, together with R.sup.3, represents alkanediyl, alkylene(di)oxy or halogenoalkylenedioxy,
The substituted 1,2,4-oxadiazole derivatives, to be used in accordance with the invention, are generally defined by the formula (I). In accordance with the invention, those compounds of the formula (I) are preferably used in which having 1 to 6 carbon atoms, which is optionally substituted by hydroxyl, halogen, C.sub.3 -C.sub.6 -cycloalkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.1 -C.sub.4 -alkyl-carbonyl, C.sub.1 -C.sub.4 -alkoxy-carbonyl or phenyl, or represents C.sub.3 -C.sub.6 -cycloalkyl or phenyl, which are in each case optionally substituted by halogen or C.sub.1 -C.sub.4 -alkyl, or represents pyridyl, furyl or thienyl, or represents alkyl, alkoxy or alkylthio having in each case 1 to 4 carbon atoms, which are in each case optionally substituted by halogen, or represents alkyl, alkoxy or alkylthio having in each case 1 to 4 carbon atoms, which are in each case optionally substituted by halogen, and represents alkyl, halogenoalkyl, alkoxy, halogenoalkoxy, alkylthio, halogenoalkylthio, alkylsulphinyl, halogenoalkylsulphinyl, alkylsulphonyl, halogenoalkylsulphonyl, alkylamino, dialkylamino, alkylcarbonylamino, alkylcarbonyl, alkylcarbonyloxy, alkoxycarbonyl, alkoxyalkyl, hydroxyalkoxy or alkoxyalkoxy having in each case 1 to 4 carbon atoms, or represents phenyl, phenoxy, benzyloxy, phenylthio, benzylthio, phenylsulphinyl or phenylsulphonyl, which are in each case optionally substituted by halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -halogenoalkyl, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -halogenoalkoxy, or, together with R.sup.3, represents C.sub.3 -C.sub.4 -alkanediyl, C.sub.1 -C.sub.3 -alkylene(di)oxy or C.sub.1 -C.sub.2 -halogenoalkylenedioxy.
In accordance with the invention, those compounds of the formula (I) are used in particular in which C.sub.1 -C.sub.4 -alkyl, which is optionally substituted by fluorine, chlorine, bromine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl or ethoxycarbonyl, or represents cyclopropyl, cyclopentyl, cyclohexyl or thienyl, or represents alkyl, alkoxy or alkylthio having in each case 1 to 4 carbon atoms, which are in each case optionally substituted by fluorine and/or chlorine, or represents alkyl having 1 to 4 carbon atoms, which is in each case optionally substituted by fluorine and/or chlorine, and trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, ch

REFERENCES:
patent: 3192103 (1965-06-01), Sousa et al.
patent: 4012377 (1977-03-01), Claisse et al.
Chemical Abstract, vol. 109, 1988, p. 18; CA# 142067v: "Action of potent cholinergic anthlemintics . . . ", R. D. Pinnock, et al.
J. C. S. Perkin I, pp. 2241-2249, Nov. 29, 1972; "Some 5-Unsubstituted Acetylenic and Vinylic 1,2,4-Oxadiazoles", J. A. Claisse et al.

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