1,2,4-oxadiazole derivatives and their use as parasiticides for

Details 1,2,4-oxadiazole derivatives and their use as parasiticides for 1,2,4-oxadiazole derivatives and their use as parasiticides for

1996-07-11

1999-11-16

Stockton, Laura L.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

514340, 5462694, 548131, A61K 3141, C07D27106

Patent

active

059859040

DESCRIPTION:

BRIEF SUMMARY
The invention relates to new 1,2,4-oxadiazole derivatives, to a plurality of processes for their preparation, and to their use for combating animal pests.
A range of substituted 1,2,4-oxadiazole derivatives have already been disclosed as compounds for use in the control of parasitic protozoans (cf. EP 7 529, EP 8 356), as analgesics (GB 1 198 726) or as herbicides (JP 57 175 177) (cf. also the earlier, but not published, Patent Application DE-P 42 32 418 by the Applicant Company).
Furthermore, the preparation of substituted 1,2,4-oxadiazole derivatives, such as, for example, 5-(4-chlorophenyl)-3-[2-(2,4-dichlorophenyl)ethyl]-1,2,4-oxadiazole and 5-(2,4-dichlorophenyl)-3-[2-(2,4-dichlorophenyl)ethyl]-1,2,4-oxadiazole is described (J. Heterocycl. Chem., 15 (8), 1373-8, 1978). However, its use for combating animal pests has not been disclosed.
New 1,2,4-oxadiazole derivatives have now been found, of the formula (I) ##STR2## in which R.sup.1 represents halogen, alkyl or alkoxy, alkylenethio, oxyalkylene, oxyalkyleneoxy, alkyleneoxyalkylene, alkenediyl or alkindiyl, halogenoalkinyl, optionally substituted cycloalkyl, optionally substituted phenyl or optionally substituted pyridyl, or one or two CH.sub.2 groups which are not bonded directly to each other to be replaced by oxygen and/or sulfur, halogenoalkoxy, 5-(2,4-dichlorophenyl)-3-[2-(2,4-dichlorophenyl)ethyl]-1,2,4-oxadiazole (cf. J. Heterocycl. Chem. 15 (8), 1373-8, 1978) and 3-(4-tert-butyl-phenoxymethyl)-5-(2,6-difluorophenyl)-1,2,4-oxadiazole (cf. DE-P 42 32 418).
Depending on the nature of the substituents, the compounds of the formula (I) can exist in the form of geometric and/or optical isomers or variously composed isomer mixtures. The invention relates to the pure isomers as well as to the isomer mixtures.
Furthermore, it has been found that the new 1,2,4-oxadiazole derivatives of the formula (I) are obtained when ##STR3## in which n, X, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 have the abovementioned meanings (V) ##STR4## in which R.sup.1, R.sup.2, m and Y have the abovementioned meanings, ##STR5## in which X, Y, R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, m and n have the abovementioned meanings a diluent and if appropriate in the presence of a reaction auxiliary, or ##STR6## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, Y and m have the abovementioned meanings and formula (VIII) ##STR7## in which X, R.sup.5, R.sup.6 and n have the abovementioned meanings, in the presence of a diluent and, if appropriate, in the presence of a reaction auxiliary.
Furthermore, it has been found that the new 1,2,4-oxadiazole derivatives of the formula (I) are highly suitable for combating animal pests. In particular, they are distinguished by a powerful activity against arthropods and nematodes.
Surprisingly, the new 1,2,4-oxadiazole derivatives of the formula (I) according to the invention show considerably better activity against animal pests than the prior art compounds which have a similar constitution.
Formula (I) provides a general definition of the compounds according to the invention.
Preferred substituents or ranges of the radicals mentioned in the formulae hereinabove and hereinbelow are illustrated in the following text: -alkyl or C.sub.1 -C.sub.6 -alkoxy. C.sub.1 14 C.sub.6 -halogenoalkyl or C.sub.1 -C.sub.6 -halogenoalkoxy. -C.sub.8 -)-alkyl-silyl-(C.sub.1 -C.sub.6 -)-alkyl or tri-(C.sub.1 -C.sub.8 -)-alkyl-silyl-(C.sub.1 -C.sub.6 -)-alkoxy; or a group --A.sub.k --R.sup.7, C.sub.1 -C.sub.6 -alkyleneoxy, C.sub.1 -C.sub.6 -alkylenethio, C.sub.1 -C.sub.6 -oxyalkylene, C.sub.1 -C.sub.6 -oxyalkyleneoxy, C.sub.1 -C.sub.6 -alkyleneoxy-C.sub.1 -C.sub.6 -alkylene, C.sub.2 -C.sub.5 -alkenediyl or C.sub.2 -C.sub.5 -alkindiyl, C.sub.2 -C.sub.20 -alkinyl, each of which is optionally monosubstituted or polysubstituted by fluorine and/or chlorine, or represents C.sub.3 -C.sub.12 -cycloalkyl which is optionally monosubstituted to tri-substituted by identical or different substituents and in which one or two CH.sub.2 groups which are not directly adjacent are optio

REFERENCES:
patent: 5037467 (1991-08-01), Cho et al.
patent: 5428047 (1995-06-01), Jeschke et al.

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