Condensed nitrogen heterocycles and their use as pesticides, fun

Details Condensed nitrogen heterocycles and their use as pesticides, fun Condensed nitrogen heterocycles and their use as pesticides, fun

1996-01-11

1998-10-13

Grumbling, Matthew V.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

514250, 514258, 544279, 544283, 544284, 544287, 544293, 544350, A61K 3154, A61K 31535, C07D40302, C07D40314

Patent

active

058212442

DESCRIPTION:

BRIEF SUMMARY
This application claims priority under 35 U.S.C. .sctn. 371 from PCT/EP94/00643, filed Mar. 4, 1994.
It has already been disclosed that certain 4-amino- and 4-alkoxy-substituted quinolines, cinnolines, naphthyridines, pyridopyrimidines and pteridines show a fungicidal, acaricidal and insecticidal activity (cf. EP-A-326 328, EP-A-326 330, EP-A-326 331, EP-A-410 762, EP-A-414 386). However, the biological activity of these compounds is not satisfactory in all fields of application, in particular when low application rates and concentrations are used.
Novel 4-amino- and 4-alkoxy-substituted condensed nitrogen heterocycles of the formulae 1a to 1d ##STR2## in which the radicals and groups are defined below, which are well tolerated by plants and of favorable toxicity to warm-blooded species while being highly suitable for controlling animal pests, such as insects, arachnids, nematodes, helminths and molluscs, for controlling endo- and ectoparasites in the field of veterinary medicine and for controlling fungal pests, have been found.
The invention therefore relates to compounds of the formula I ##STR3## in which two of the symbols A, B, D and E are in each case CR.sup.1 and the remaining two symbols are in each case CH or in each case nitrogen, or (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-alkoxy, halo-(C.sub.1 -C.sub.4)-alkyl or halo-(C.sub.1 -C.sub.4)-alkoxy, where, preferably, one radical R.sup.1 is always hydrogen, -C.sub.4)-alkoxy, halo-(C.sub.1 -C.sub.4)-alkyl or halo-(C.sub.1 -C.sub.4)-alkoxy, -C.sub.4)-alkanediyl group, ##STR4## in which n is an integer from 2 to 7, R.sup.4 and R.sup.5 are identical or different and are in each case hydrogen, (C.sub.1 -C.sub.12)-alkyl, (C.sub.3 -C.sub.8)-cycloalkyl, (C.sub.3 -C.sub.8)-cycloalkyl-(C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.8)-alkoxy, (C.sub.3 -C.sub.8)-cycloalkoxy, (C.sub.1 -C.sub.4)-alkoxy-(C.sub.1 -C.sub.4)-alkyl, (C.sub.3 -C.sub.8)-cycloalkyl-(C.sub.1 -C.sub.4)-alkoxy, (C.sub.1 -C.sub.8)-alkoxycarbonyl, (C.sub.1 -C.sub.4)-alkoxy-(C.sub.1 -C.sub.4)-alkylcarbonyl, (C.sub.3 -C.sub.8)-cycloalkoxycarbonyl, (C.sub.1 -C.sub.8)-alkylcarbamoyl, di-(C.sub.1 -C.sub.8)-alkylcarbamoyl, N-piperidinocarbonyl, N-morpholino-carbonyl, (C.sub.3 -C.sub.8)-cycloalkylcarbamoyl, (C.sub.1 -C.sub.8)-alkylcarbonyloxy, (C.sub.3 -C.sub.8)-cycloalkylcarbonyloxy, (C.sub.1 -C.sub.8)-alkylcarbonylamino, (C.sub.3 -C.sub.8)-cycloalkylcarbonylamino, tri-(C.sub.1 -C.sub.8)-alkylsilyl, preferably dimethyl-(C.sub.1 -C.sub.8)-alkylsilyl or triethylsilyl, di-(C.sub.1 -C.sub.8)-alkyl-(C.sub.3 -C.sub.8)-cycloalkylsilyl, preferably dimethylcyclohexylsilyl, di-(C.sub.1 -C.sub.8)-alkyl-(phenyl-(C.sub.1 -C.sub.4)-alkyl)silyl, preferably dimethyl-(phenyl-(C.sub.1 -C.sub.4)-alkyl-silyl, di-(C.sub.1 -C.sub.8)-alkyl-(C.sub.1 -C.sub.4)-haloalkylsilyl, preferably dimethyl-(C.sub.1 -C.sub.4)-haloalkylsilyl, dimethylphenylsilyl, (C.sub.1 -C.sub.4)-haloalkyl, halogen, (C.sub.1 -C.sub.4)-haloalkoxy, (C.sub.1 -C.sub.4)-haloalkoxycarbonyl, (C.sub.1 -C.sub.4)-haloalkylcarbamoyl, (C.sub.3 -C.sub.8)-haloalkylcarbonyloxy, (C.sub.3 -C.sub.8)-haloalkylcarbonylamino, heteroaryl, phenyl, naphthyl, biphenylyl, phenyl-(C.sub.1 -C.sub.4)-alkyl, benzyloxy, benzyloxy-(C.sub.1 -C.sub.4)-alkyl, benzylthio, phenoxycarbonyl, benzyloxycarbonyl, phenylcarbamoyl, benzylcarbamoyl, benzoyloxy, phenylacetyloxy, benzoylamino, phenylacetylamino, phenylthio or phenoxy, it being possible for the phenyl rings in the 17 last-mentioned radicals and in heteroaryl to be unsubstituted or provided with one or two substituents, and these substituents are identical or different and can in each case be (C.sub.1 -C.sub.8)-alkyl, (C.sub.3 -C.sub.8)-cycloalkyl, (C.sub.1 -C.sub.4)-haloalkyl, preferably trifluoromethyl, halogen, (C.sub.1 -C.sub.4)-dialkylamino, (C.sub.1 -C.sub.4)-alkylthio, (C.sub.1 -C.sub.8)-alkoxy, (C.sub.1 -C.sub.4)-haloalkoxy, (C.sub.1 --CH.sub.2 --O--!.sub.x where x=2, 3 or 4, 2-(tetrahydro-2H-pyran-2-yloxy)-ethoxy, (C.sub.2 -C.sub.8)-alkenyl, (C.sub.2 -C.sub.8)-alkynyl, benzyloxy, which optionally has one or two identical or

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