Heterocyclylbenzonitriles

Details Heterocyclylbenzonitriles Heterocyclylbenzonitriles

2000-08-22

2002-05-28

Morris, Patrica L. (Department: 1625)

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

C546S121000

Reexamination Certificate

active

06395683

ABSTRACT:

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-difluoro-4-(4,5,6,7-tetrahydro-3-methyl-2H-indazol-2-yl)-benzonitrile and 4-[5-(t-butyl)-2-oxo-1,3,4-oxadiazol-3(2H)-yl]-2,5-difluoro-benzonitrile, 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)
in which
R
1
represents hydrogen or halogen,
R
2
represents hydrogen, or represents formyl, or represents in each case optionally substituted alkyl, alkenyl, alkinyl, alkoxy, alkylcarbonyl, alkoxycarbonyl, alkylsulphonyl, cycloalkyl, cycloalkylalkyl, cycloalkylcarbonyl, cycloalkylsulphonyl, arylalkyl, arylcarbonyl, arylalkylcarbonyl, aryloxycarbonyl, arylsulphonyl, arylalkylsulphonyl or heteroarylsulphonyl,
R
3
represents in each case optionally substituted alkyl, cycloalkyl, aryl, arylalkyl or heteroaryl and
Het represents one of the heterocyclic groupings listed below (bonded via N)
 wherein, in each case, where appropriate,
A represents C
1
-C
4
-alkanediyl which is optionally interrupted by SO
2
and
Q represents oxygen or sulphur, and wherein the heterocyclic groupings 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
1
-C
4
-alkyl, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-halogenoalkoxy or phenyl, and
R represents a radical from the series consisting of hydrogen, hydroxyl, cyano, nitro, C
1
-C
4
-alkyl, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-halogenoalkoxy or phenyl,
have now been found.
It has furthermore been found that heterocyclylbenzonitriles of the general formula (I) are obtained by a procedure in which
(a) anhydrides of the general formulae (IIa) to (IIg)
 in which
Q has the abovementioned meaning, are reacted with aminobenzonitriles of the general formula (III)
 in which
R
1
, R
2
and R
3
have the abovementioned meanings,
if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary,
or by a procedure in which
(b) halogenated heterocyclylbenzonitriles of the general formula (IV)
 in which
Het and R
1
have the abovementioned meanings and
X
1
represents halogen, are reacted with sulphonamides of the general formula (V)
 in which
R
2
and R
3
have the abovementioned meanings,
if appropriate in the presence of a diluent and if appropriate in the 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-difluoro-4-(4,5,6,7-tetrahydro-3-methyl-2H-indazol-2-yl)-benzonitrile and 4-[5-(t-butyl)-2-oxo-1,3,4-oxadiazol-3(2H)-yl]-2,5-difluoro-benzonitrile known 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
R
1
represents hydrogen or halogen,
R
2
represents hydrogen, or represents formyl, or represents alkyl, 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
1
-C
4
-alkoxy or C
1
-C
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
1
-C
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
1
-C
4
-alkyl, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-halogenoalkoxy or C
1
-C
4
-alkoxycarbonyl),
R
3
represents alkyl, alkenyl or alkinyl having in each case up to 10 carbon atoms and in each case optionally substituted by halogen, cyano or C
1
-C
4
-alkoxy, or represents cycloalkyl or cycloalkylalkyl having 3 to 8 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
1
-C
4
-alkyl, or represents aryl or arylalkyl having 6 or 10 carbon atoms in the aryl part and 1 to 4 carbon atoms in the alkyl part and in each case optionally substituted by halogen, cyano, nitro, carboxyl or carbamoyl, by C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-alkylsulphinyl or C
1
-C
4
-alkylsulphonyl (which are in each case optionally substituted by fluorine and/or chlorine), or by dimethylaminosulphonyl, diethylaminosulphonyl, dimethylaminocarbonyl or diethylaminocarbonyl, or by C
1
-C
4
-alkoxy-carbonyl (which is optionally substituted by halogen, methoxy or ethoxy), or by phenyl, phenyloxy or phenylthio (which are in each case optionally substituted by halogen, cyano, methyl, methoxy, trifluoromethyl and/or trifluoromethoxy), or represents heterocyclyl or heterocyclylalkyl having 2 to 6 carbon atoms and 1 to 4 nitrogen atoms and/or 1 to 2 oxygen or sulphur atoms in the saturated or unsaturated heterocyclyl part and, where appropriate, 1 to 4 carbon atoms in the alkyl part and in each case optionally substituted by halogen, cyano, nitro, carboxyl or carbamoyl, or by C
1
-C
4
-alkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-alkylthio, C
1
-C
4
-alkylsulphinyl, C
1
-C
4
-alkylsulphonyl or C
1
-C
4
-alkoxycarbonyl (which are in each case optionally substituted by halogen) or by phenyl, phenoxy or phenylthio (which are in each case optionally substituted by halogen, cyano, C
1
-C
4
-alkyl, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-alkoxy and/or C
1
-C
4
-halogenoalkoxy), and
Het represents one of the heterocyclic groupings listed below (bonded via N)
 wherein in each case, where appropriate,
A represents C
1
-C
3
-alkanediyl which is optionally interrupted by SO
2
and
Q represents oxygen or sulphur, and wherein the heterocyclic groupings mentioned are in each case optionally substituted once to three times by identical or different radicals from the series consisting of hydroxyl, halogen, cyano, nitro, C
1
-C
4
-alkyl, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-halogenoalkoxy or phenyl and
R represents a radical from the series consisting of hydrogen, hydroxyl, cyano, nitro, C
1
-C
4
-alkyl, C
1
-C
4
-halogenoalkyl, C
1
-C
4
-alkoxy, C
1
-C
4
-halogenoalkoxy or phenyl.
The invention particularly relates to compounds of the formula (I) in which
R
1
represents hydrogen, fluorine or chlorine,
R
2
represents hydrogen, or represents formyl, or represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, propenyl, butenyl, propinyl, butinyl, methoxy, ethoxy, n- or i-propoxy, n-, i- or s-butoxy, acetyl, propionyl, butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl or n-, i-, s- or t-butylsulphonyl, in each case optionally substituted by fluorine, chlorine, cyano, methoxy, ethoxy, methoxycarbonyl or ethoxycarbonyl, or represents cyclopropyl, cyclobu

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