Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1996-08-12
1998-12-15
Fan, Jane
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
5483687, 5483717, 5483714, A61K 31415, C07D23152
Patent
active
058497781
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/EP95/00416, Feb. 6, 1995 now WO95/22,530.
The present invention relates to new N-pyrazolylanilines and N-pyrazolylaminopyridines, to processes for their preparation, and to their use as pesticides.
It is known that certain N-heteroaryl-2-nitro-anilines such as, for and laniline, have fungicidal and insecticidal properties (cf. EP-A-0 478 974, WO 93/19 054). However, the activity of these compounds is not always entirely satisfactory under certain circumstances, in particular when low concentrations of active compound and low application rates are used.
New N-pyrazolylanilines and N-pyrazolylaminopyridines of the formula (I) ##STR2## have now been found, in which X represents C--NO.sub.2, C-halogen, C-halogenoalkyl or N, halogenoalkylthio, alkenyl, alkinyl, aryl, hetaryl or aralkyl, halogen, cyano or nitro, or in each case optionally substituted alkyl, aryl or hetaryl, or one of the radicals CO.sub.2 R.sup.5, CONR.sup.6 R.sup.7, CSNR.sup.6 R.sup.7, S(O).sub.n R.sup.8, alkenyl, alkinyl, aralkyl, aryloxy or aralkyloxy or one of the radicals SO.sub.2 NR.sup.6 R.sup.7, SO.sub.2 R.sup.9, COR.sup.10 or CH.sub.2 N(R.sup.9).sub.w, in which alkyl, or together with the N atom to which they are bonded form a ring which optionally contains at least one further hetero atom, aryl or aryloxy, and substituted phenylsulfonyl or pyridyl and/or phenyl, optionally substituted phenylsulfonyl, CO.sub.2 -alkyl or CO.sub.2 -benzyl, NO.sub.2.
Furthermore, it has been found that A) the N-pyrazolylanilines and N-pyrazolylaminopyridines of the formula (I) are obtained by a process which comprises reacting 5-aminopyrazoles of the formula (II) ##STR3## in which R.sup.1, R.sup.2 and R.sup.3 have the abovementioned meanings with compounds of the formula (III) ##STR4## in which Hal represents fluorine, chlorine, bromine or iodine, preferably fluorine or chlorine, and the presence of a diluent, and, if appropriate, subsequently reacting the resulting compounds of the formula (Ia) ##STR5## in which X, Y, Z, R.sup.1, R.sup.2 and R.sup.3 have the abovementioned meanings with compounds of the formula (IV) bromine, iodine, acetoxy, tosyl or mesyl and hydrogen in the presence of a base and if appropriate in the presence of a diluent, and that B) compounds of the formula (Ib) ##STR6## in which R.sup.1, R.sup.2, R.sup.3, X, Y and Z have the abovementioned meanings and comprises reacting 5-aminopyrazoles of the formula (II) ##STR7## in which R.sup.1, R.sup.2 and R.sup.3 have the abovementioned meanings with compounds of the formula (IV) and in the presence of a diluent, and subsequently reacting the resulting compounds of the formula (V) ##STR8## in which R.sup.1, R.sup.2, R.sup.3 and R.sup.11 have the abovementioned meanings with compounds of the formula (III) ##STR9## in which Hal, X, Y and Z have the abovementioned meanings in the presence of a base and in the presence of a diluent.
The new compounds of the formula (I) have properties which allow them to be used as pesticides. In particular, they can be used as insecticides, arthropodicides and fungicides.
Formula (I) provides a general definition of the N-pyrazolylanilines and N-pyrazolylaminopyridines according to the invention.
Preferred substituents or ranges of the radicals listed in the formulae mentioned hereinabove and hereinbelow will be illustrated in the following text. -halogenoalkyl or N. -halogenoalkyl. C.sub.1 -C.sub.6 -halogenoalkoxy or C.sub.1 -C.sub.6 -halogenoalkylthio. -C.sub.8 -cyanoalkyl, C.sub.1 -C.sub.8 -halogenoalkyl, C.sub.1 -C.sub.8 -hydroxyalkyl, C.sub.1 -C.sub.4 -alkoxy-C.sub.1 -C.sub.8 -alkyl, or represents phenyl, benzyl or phenethyl, each of which is optionally monosubstituted to trisubstituted by identical or different substituents from the series consisting of halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -halogenoalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -halogenoalkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -halogenoalkylthio, phenyl, phenoxy, CN or NO.sub.2, or represents pyridyl which is monosubstituted to
REFERENCES:
CA111:232751 Chakrabarti et al.,1989.
Dehne Heinz-Wilhelm
Erdelen Christoph
Heil Markus
Lui Nobert
Wachendorff-Neumann Ulrike
Bayer Aktiengesellschaft
Fan Jane
LandOfFree
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