Heterocyclylbenzonitriles

Details Heterocyclylbenzonitriles Heterocyclylbenzonitriles

1996-10-21

1999-01-12

Morris, Patricia L.

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

548513, A01N 4338, C07D20902

Patent

active

058589252

DESCRIPTION:

BRIEF SUMMARY
The invention relates to new heterocyclylbenzonitriles, processes and new intermediate products for their preparation and their use as herbicides.
It is already known that certain heterocyclylbenzonitriles, such as, for example, the compounds 2,5-difluoro4-(4,5,6,7-tetrahydro-3-methyl-2H-indazol-2-yl)benzonitrile le, have herbicidal properties (cf. EP-A 370332, Examples 2 and 7; cf. also EP-A 364797 and EP-A 558999). However, the activity of these compounds which are already known is not completely satisfactory in all fields of use, especially when low amounts are applied and at low concentrations.
The new heterocyclylbenzonitriles of the general formula (I) ##STR2## in which R.sup.1 represents hydrogen or halogen, case optionally substituted alkyl, alkenyl, alkinyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylsulphonyl, cycloalkyl, cycloalkylalkyl, cycloalkylcarbonyl, cycloalkylsulphonyl, arylalkyl, arylcarbonyl, arylalkylcarbonyl, aryloxycarbonyl, arylsulphonyl, arylalkylsulphonyl or heteroarylsulphonyl, aryl, arylalkyl or heteroaryl and N) ##STR3## wherein, in each case, where appropriate, A represents C.sub.1 -C.sub.4 -alkanediyl which is optionally interrupted by SO.sub.2 and mentioned in each case are optionally substituted once to four times by identical or different radicals from the series consisting of hydroxyl, halogen, cyano, nitro, 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 or phenyl, and cyano, nitro, 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 or phenyl,
It has furthermore been found that heterocyclylbenzonitriles of the general formula (I) are obtained by a procedure in which ##STR4## in which Q has the abovementioned meaning, ##STR5## in which R.sup.1, R.sup.2 and R.sup.3 have the abovementioned meanings, presence of a reaction auxiliary, ##STR6## in which Het and R.sup.1 have the abovementioned meanings and ##STR7## in which R.sup.2 and R.sup.3 have the abovementioned meanings, presence of an acid acceptor.
The new heterocyclylbenzonitriles of the general formula (I) are distinguished by a potent herbicidal activity.
Surprisingly, the compounds of the formula (I) according to the invention show a considerably more potent action against weeds, coupled with a good tolerance with respect to crop plants, such as, for example, barley, than the structurally similar compounds 2,5-difluoro4-(4,5,6,7-tetrahydro-3-methyl-2H-indazol-2-yl)-benzonitrile and own from the prior art.
In the definitions, the saturated or unsaturated hydrocarbon chains, such as alkyl, alkenyl or alkinyl, are in each case straight-chain or branched.
Halogen in general 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 alkenyl, alkinyl, alkoxy, alkylcarbonyl, alkoxycarbonyl or alkylsulphonyl having in each case up to 6 carbon atoms and in each case optionally substituted by halogen, cyano, C.sub.1 -C.sub.4 -alkoxy or C.sub.1 -C.sub.4 -alkoxy-carbonyl, or represents cycloalkyl, cycloalkylalkyl, cycloalkylcarbonyl or cycloalkylsulphonyl having 3 to 6 carbon atoms in the cycloalkyl part and, where appropriate, 1 to 4 carbon atoms in the alkyl part and in each case optionally substituted by halogen, cyano or C.sub.1 -C.sub.4 -alkyl, or represents phenylmethyl, phenylcarbonyl, naphthylcarbonyl, phenylmethylcarbonyl, phenoxycarbonyl, phenylsulphonyl, naphthylsulfonyl, phenylmethylsulphonyl, thienylsulphonyl, pyrazolylsulphonyl, pyridinylsulphonyl or pyridinylmethylsulphonyl (which are in each case optionally substituted by halogen, cyano, 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 or C.sub.1 -C.sub.4 -alkoxycarbonyl), carbon atoms and in each case optionally substituted by halogen, cyano or C.sub.1 -C.sub.4 -alkoxy, or represents cycloalkyl or cycloalkylalkyl having

REFERENCES:
patent: 5221318 (1993-06-01), Fischer et al.
Cran & Hammond, "Organic Chemistry", McGraw-Hill Book Co., NY (1964) 2nd Ed pp. 565-567.

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