Substituted 1,2,3,4-tetrahydro-5-nitro-pyrimidines

Details Substituted 1,2,3,4-tetrahydro-5-nitro-pyrimidines Substituted 1,2,3,4-tetrahydro-5-nitro-pyrimidines

1996-07-12

1999-02-09

Ford, John M.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

544319, C07D48704, A01N 4354

Patent

active

058694919

DESCRIPTION:

BRIEF SUMMARY
This is a 371 of PCT/EP95/00058 filed Jan. 9, 1995.
The present invention relates to new substituted 1,2,3,4-tetrahydro-5-nitro-pyrimidines, to processes for their preparation, and to their use in pesticides, in particular as insecticides.
In addition, the new compounds have a highly pronounced ectoparasiticidal activity.
Furthermore, it is known that certain nitrated nitrogen heterocycles have insecticidal properties (cf. EP 0 316 843; EP 0 375 613).
The new substituted 1,2,3,4-tetrahydro-5-nitro-pyrimidines of the formula (I) have been found, ##STR2## in which Het represents optionally substituted pyridyl or thiazolyl, 6-membered ring which optionally contains N or O as further hetero atom and which is optionally substituted, which is optionally substituted by phenyl, halogen, OH, CN or the radical NR.sup.4 R.sup.5, where R.sup.4 ard R.sup.5 represent hydrogen, C.sub.1-4 -alkyl or phenyl, and which is optionally interrupted once or more than once by O, S, ##STR3## A furthermore represents optionally substituted cycloalkylene, R.sup.3 represents one of the radicals ##STR4## where R.sup.6 represents alkyl, cycloalkyl, alkenyl, aryl, aralkyl, heteroaryl, alkoxy, cycloalkoxy, alkenoxy, aryloxy, aralkoxy, heteroaryloxy, alkylthio, arylthio, aralkylthio, heteroarylthio, amino, alkylamino, dialkylamino, arylamino, aryl-alkylamino, aralkylamino, aralkyl-alkylamino, it being possible for the radicals to be optionally substituted,
Furthermore, it has been found that the substituted 1,2,3,4-tetrahydro-5-nitro-pyrimidines of the formula (I) are obtained when ##STR5## in which Het, R.sup.1 and R.sup.2 have the abovementioned meanings, appropriate in the presence of acidic catalysts and if appropriate in the presence of diluents, or ##STR6## or the radical ##STR7## nitromethylene derivatives of the formulae IV or IVa ##STR8## in which Het, R.sup.1, R.sup.2 and A have the abovementioned meanings, are reacted with compounds of the formula (V) ##STR9## in which Z represents a leaving group, such as halogen, or the radical ##STR10## and X and R.sup.6 have the abovementioned meanings, which have been mentioned under R.sup.6, in the presence of diluents and/or catalysts, or adjacent atoms do not cyclize, nitromethylene derivatives of the formula (A) ##STR11## in which R.sup.10 represents C.sub.1 -C.sub.4 -alkyl or phenyl, of diluents and/or catalysts.
The present invention also relates to the nitromethylene derivatives of the formulae (IVb), (IVc) and (IVd) ##STR12## in which R.sup.1, R.sup.2 and A have the abovementioned meanings, ##STR13## in which, R.sup.1, R.sup.2 and A have the abovementioned meanings, ##STR14## in which R.sup.1 and R.sup.2 have the abovementioned meanings and ##STR15##
Optionally substituted alkyl in the general formulae denotes straight-chain or branched alkyl having preferably 1 to 12, in particular 1 to 6, carbon atoms. The following may be mentioned by way of example and as being preferred: optionally substituted methyl, ethyl, n- and i-propyl and n-, i- and t-butyl.
Optionally substituted alkenyl and the alkenyl moiety of optionally substituted alkenyloxy and alkenylthio in the general formulae denote straight-chain or branched alkenyl having preferably 2 to 6, in particular 2 to 4, carbon atoms. The following may be mentioned by way of example and as being preferred: optionally substituted ethenyl, propene-1-yl, propene-2-yl and butene-3-yl.
Optionally substituted cycloalkyl or cycloalkylene in the general formulae denotes mono-, bi- and tricyclic cycloalkyl having preferably 3 to 10, in particular 3, 5 or 6, carbon atoms. The following may be mentioned by way of example and as being preferred: optionally substituted cyclopropyl, adamantyl.
Optionally substituted alkoxy in the general formulae denotes straight-chain or branched alkoxy having preferably 1 to 6, in particular 1 to 4, carbon atoms. The following may be mentioned by way of example and as being preferred: optionally substituted methoxy, ethoxy, n- and i-propoxy and n-, s- and t-butoxy.
Optionally substituted alkylthio in the general

REFERENCES:
Patent Abstracts of Japan, vol. 16, No. 71 (1991) (English Abstract of WO 90/05134).

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