Plant protecting and regulating compositions – Plant growth regulating compositions – Organic active compound containing
Patent
1996-09-24
1999-10-05
Raymond, Richard L.
Plant protecting and regulating compositions
Plant growth regulating compositions
Organic active compound containing
514274, 544311, 544312, 544309, A01N 4354, C07D23902
Patent
active
059623721
DESCRIPTION:
BRIEF SUMMARY
The invention relates to new N-cyanoaryl nitrogen heterocycles, to a plurality of processes for their preparation, to their use as herbicides and insecticides, and to new intermediates.
It has already been disclosed that certain N-cyanoaryl nitrogen heterocycles have herbicidal properties (cf. WO 91/00278, WO 92/11244, DE 4237920, EP 408382/US 5084084, EP 438209, EP 473551). However, the herbicidal action, and the tolerance of the prior-art N-cyanoaryl nitrogen heterocycles with regard to crop plants, are not entirely satisfactory.
There have now been found the new N-cyanoaryl nitrogen heterocycles of the general formula (I) ##STR2## in which R.sup.1 represents hydrogen or halogen, ##STR3## where n represents the numbers 0 or 1, alkinyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl, substituted alkylcarbonyl, alkoxycarbonyl, alkylsulphonyl, cycloalkylcarbonyl, cycloalkylalkylcarbonyl, cycloalkylsulphonyl, cycloalkylalkylsulphonyl, arylcarbonyl, arylalkylcarbonyl, aryloxycarbonyl, arylsulphonyl, heterocyclylsulphonyl or heterocyclylalkylsulphonyl, alkyl, represents alkanediyl, ##STR4## where R.sup.5 represents hydrogen or in each case optionally substituted alkyl, alkenyl, alkinyl, alkylcarbonyl or alkoxycarbonyl, or represents amino or hydroxyl (in each case only bonded to N).
The general formula (I) thus represents the isomeric compounds of the general formulae (IA) and (IB) below ##STR5##
The new N-cyanoaryl nitrogen heterocycles of the general formula (I) are obtained when represents hydrogen and R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the abovementioned meanings, ##STR6## in which R.sup.3 and R.sup.4 have the abovementioned meanings and ##STR7## in which R.sup.1 and R.sup.2 have the abovementioned meanings, (IV) ##STR8## in which R.sup.1 and R.sup.2 have the abovementioned meanings and in the presence of a diluent, represents in each case optionally substituted alkyl, alkenyl, alkinyl, alkylcarbonyl or alkoxycarbonyl and R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the abovementioned meanings, R.sup.4 have the abovementioned meanings, formulae (V) or (VI) alkinyl, alkylcarbonyl or alkoxycarbonyl and the presence of a diluent, following group ##STR9## and n, A.sup.1, A.sup.2, A.sup.3, R.sup.1, R.sup.3, R.sup.4 and Z have the abovementioned meanings, R.sup.2 represents the group --NH--SO.sub.2 --A.sup.1 and A.sup.1, R.sup.1, R.sup.3, R.sup.4 and Z have the abovementioned meanings, the presence of a diluent, or when amino or hydroxyl and R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the abovementioned meanings, in which R.sup.5 represents hydrogen and R.sup.1, R.sup.2, R.sup.3 and R.sup.4 have the abovementioned meanings, appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent.
The new N-cyanoaryl nitrogen heterocycles of the general formula (I) are distinguished by a powerful herbicidal activity.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkanediyl, alkenyl or alkinyl, are in each case straight-chain or branched.
Halogen generally represents fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
The invention preferably relates to compounds of the formula (I) in which ##STR10## in which n represents the numbers 0 or 1, or alkinyl, each of which has up to 10 carbon atoms and each of which is. optionally substituted by halogen, cyano or C.sub.1 -C.sub.4 -alkoxy, carbon atoms in the cycloalkyl moiety and, if appropriate, 1 to 4 carbon atoms in the alkyl moiety, each of which is optionally substituted by halogen, cyano or C.sub.1 -C.sub.4 -alkyl, atoms in the aryl moiety and 1 to 4 carbon atoms in the alkyl moiety, each of which is optionally substituted by halogen, cyano, nitro, carboxyl, carbamoyl, by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -alkylsulphonyl or C.sub.1 -C.sub.4 -alkylsulphonyl (which are in each case optionally substituted by fluorine and/or chlorine), by dimeth
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Andree Roland
Dollinger Markus
Drewes Mark Wilhelm
Erdelen Christoph
Santel Hans-Joachim
Bayer Aktiengesellschaft
Kifle Bruck
Raymond Richard L.
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