Substituted herbicidal phenyluracils

Abstract

The invention relates to novel substituted phenyluracils of the general formula (I) in which m, n, Q, R 1 , R 2 , R 3 , R 4 , R 5 , X and Y are each as defined in the description, to processes for their preparation, to novel intermediates and to their use as herbicides.

1 . Substituted phenyluracils of the general formula (I)  
       
         
           
           
               
               
           
         
       
       in which 
 m represents 0, 1, 2 or 3,  
 n represents 0, 1, 2, 3 or 4,  
 Q represents O (oxygen), S (sulphur), SO, SO 2 , NH or N(alkyl),  
 R 1  represents hydrogen, amino or optionally substituted alkyl,  
 R 2  represents carboxyl, cyano, carbamoyl, thiocarbamoyl or in each case optionally substituted alkyl or alkoxycarbonyl,  
 R 3  represents hydrogen, halogen or optionally substituted alkyl,  
 R 4  represents hydrogen, cyano, carbamoyl, thiocarbamoyl or halogen,  
 R 5  represents cyano, carbamoyl, thiocarbamoyl, halogen or in each case optionally substituted alkyl or alkoxy,  
 X represents hydroxyl, mercapto, amino, nitro, formyl, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, sulphonyl, halogenosulphonyl, or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaininocarbonyloxy, dialkylaminocarbonyloxy, alkylcarbonylamino, alkoxycarbonylamino, alkylsulphonylamino, alkenyl, alkenyloxy, alkenyloxycarbonyl, alkenylcarbonyloxy, alkinyl, alkinyloxy, alkinyloxycarbonyl, alkinylcarbonyloxy or arylcarbonyloxy, and  
 Y represents hydroxyl, mercapto, amino, nitro, formyl, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, sulphonyl, halogenosulphonyl, or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, alkylcarbonylamino, alkoxycarbonylamino, alkylsuipholnylamino, alkenyl, alkenyloxy, alkenyloxycarbonyl, alkenylcarbonyloxy, alkinyl, alkinyloxy, alkinyloxycarbonyl, alkinylcarbonyloxy or arylcarbonyloxy, 
 where, in the case that m and/or are greater than 1, X and Y in the individual compounds possible in each case have identical or different meanings from those given,  
 and salts of compounds of the formula (I).  
 
 
     
     
         2 . Compounds according to  claim 1  characterized in that 
 m represents 0, 1 or 2,  
 n represents 0, 1, 2 or 3,  
 Q represents O (oxygen), S (sulphur), SO, SO 2 , NH or N(C 1 -C 4 -alkyl),  
 R 1  represents hydrogen, amino or represents optionally cyano-, halogen- or C 1 -C 3 -alkoxy-substituted alkyl having 1 to 4 carbon atoms,  
 R 2  represents carboxyl, cyano, carbamoyl, thiocarbamoyl or represents in each case optionally cyano-, halogen- or C 1 -C 3 -alkoxy-substituted alkyl or alkoxycarbonyl having in each case 1 to 4 carbon atoms,  
 R 3  represents hydrogen, halogen or represents optionally cyano-, halogen- or C 1 -C 3 -alkoxy-substituted alkyl having 1 to 4 carbon atoms,  
 R 4  represents hydrogen, cyano, fluorine or chlorine,  
 R 5  represents cyano, carbamoyl, thiocarbamoyl, halogen or represents in each case optionally halogen-substituted alkyl or alkoxy having in each case 1 to 4 carbon atoms,  
 X represents hydroxyl, mercapto, amino, nitro, formyl, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, sulphonyl, halogenosulphonyl, represents in each case optionally cyano-, carboxyl-, carbamoyl-, halogen-, C 1 -C 4 -alkoxy-, C 1 -C 4 -alkylthio-, C 1 -C 4 -alkylsulphinyl-, C 1 -C 4 -alkylsulphonyl-, C 1 -C 4 -alkyl-carbonyl-, C 1 -C 4 -alkoxy-carbonyl-, C 2 -C 4 -alkenyloxy-carbonyl-, C 2 -C 4 -alkinyloxy-carbonyl-, C 1 -C 4 -alkylaminocarbonyl-, di-(C 1 -C 4 -alkyl)-amino-carbonyl-, phenoxycarbonyl-, benzyloxycarbonyl-, phenylaminocarbonyl- or benzylaminocarbonyl-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or alkylamino having in each case 1 to 6 carbon atoms, represents dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylamino-carbonyl, dialkylaminocarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, alkylcarbonylamino, alkoxycarbonylamino, alkylsulfonylamino, bis-alkylsulfonyl-amino or N-alkylcarbonyl-N-alkylsulphonyl-amino having in each case 1 to 6 carbon atoms in the alkyl groups, represents in each case optionally cyano-, carboxyl-, carbamoyl-, halogen-, C 1 -C 4 -alkoxy-carbonyl-, C 1 -C 4 -alkylamino-carbonyl- or di-(C 1 -C 4 -alkyl)-amino-carbonyl-substituted alkenyl, alkenyloxy, alkenyloxycarbonyl, alkenylcarbonyloxy, alkinyl, alkinyloxy, alkinyloxycarbonyl or alkinylcarbonyloxy having in each case 2 to 6 carbon atoms in the alkenyl or alkinyl groups, or represents benzyloxy, and  
 Y represents hydroxyl, mercapto, amino, nitro, formyl, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, sulphonyl, halogenosulphonyl, represents in each case optionally cyano-, carboxyl-, carbamoyl-, halogen-, C 1 -C 4 -alkoxy-, C 1 -C 4 -alkylthio-, C 1 -C 4 -alkylsulphinyl-, C 1 -C 4 -alkylsulphonyl-, C 1 -C 4 -alkyl-carbonyl-, C 1 -C 4 -alkoxy-carbonyl-, C 2 -C 4 -alkenyloxy-carbonyl-, C 2 -C 4 -alkinyloxy-carbonyl-, aminocarbonyl-, C 1 -C 4 -alkylaminocarbonyl-, di-(C 1 -C 4 -alkyl)-aminocarbonyl-, phenoxycarbonyl-, benzyloxycarbonyl-, phenylaminocarbonyl- or benzylaminocarbonyl-substituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or alkylamino having in each case 1 to 6 carbon atoms, represents dialkylamino, alkylcarbonyl, alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, dialkylaminocarbonyloxy, alkylcarbonylamino, alkoxycarbonylamino, alkylsulfonylamino, bis-alkylsulfonyl-amino or N-alkylcarbonyl-N-alkylsulphonyl-amino having in each case 1 to 6 carbon atoms in the alkyl groups, represents in each case optionally cyano-, carboxyl-, carbamoyl-, halogen-, C 1 -C 4 -alkoxycarbonyl-, C 1 -C 4 -alkylaminocarbonyl- or di-(C 1 -C 4 -alkyl)-amino-carbonyl-substituted alkenyl, alkenyloxy, alkenyloxycarbonyl, alkenylcarbonyloxy, alkinyl, alkinyloxy, alkinyloxycarbonyl or alkinylcarbonyloxy having in each case 2 to 6 carbon atoms in the alkenyl or alkinyl groups, or represents benzyloxy.  
 
     
     
         3 . Compounds according to  claim 1  or  2 , characterized in that 
 m represents 0 or 1,  
 n represents 0, 1 or 2,  
 Q represents O (oxygen) or S (sulphur),  
 R 1  represents hydrogen, amino or represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl,  
 R 2  represents carboxyl, cyano, carbamoyl, thiocarbamoyl or represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl,  
 R 3  represents hydrogen, fluorine, chlorine, bromine, or represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl,  
 R 4  represents hydrogen, fluorine or chlorine,  
 R 5  represents cyano, carbarnoyl, thiocarbamoyl, fluorine, chlorine, bromine, or represents in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy,  
 X represents hydroxyl, mercapto, amino, nitro, formyl, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, sulphonyl, chlorosulphonyl, represents in each case optionally cyano-, carboxyl-, carbanoyl-, thiocarbamoyl-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, n- or i-propylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, n- or i-propylsulphonyl-, acetyl-, propionyl-, n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, n-, i-, s- or t-butoxycarbonyl-, propenyloxycarbonyl-, butenyloxycarbonyl-, propinyloxycarbonyl-, butinyloxycarbonyl-, methylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-, dimethylaminocarbonyl-, diethylaminocarbonyl-, phenoxycarbonyl-, benzyloxycarbonyl-, phenylaminocarbonyl- or benzylaminocarbonyl-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsuliphonyl, ethylsulphonyl, n- or i-propylsulphonyl, methylamino, ethylamino, n- or i-propylamino, represents dimethylamino, diethylamino, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n-oder i-propylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, acetyloxy, propinoyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, n-, i-, s- or t-butoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, n-, i-, s- or t-butylaminocarbonyloxy, dimethylaminocarbonyloxy, diethylaminocarbonyloxy, acetylamino, propionylamino, n- or i-butyroylamino, methoxycarbonylamino, ethoxycarbonylamino, n- or i-propoxycarbonylamino, methylsulphonylamino, ethylsulphonylamino, n- or i-propylsulphonylamino, or represents in each case optionally cyano-, carboxyl-, carbamoyl-, fluorine-, chlorine-, bromine-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, methylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-, dimethylaminocarbonyl- or diethylaminocarbonyl-substituted ethenyl, propenyl, butenyl, propenyloxy, butenyloxy, propenyloxycarbonyl, butenyloxycarbonyl, ethenecarbonyloxy, propenecarbonyloxy, butenecarbonyloxy, ethinyl, propinyl, butinyl, propinyloxy, butinyloxy, propinyloxycarbonyl, butinyloxycarbonyl, ethinecarbonyloxy, propinecarbonyloxy or butinecarbonyloxy, or represents benzoyloxy,  
 Y represents hydroxyl, mercapto, amino, nitro, formyl, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, sulphonyl, chlorosulphonyl, represents in each case optionally cyano-, carboxyl-, carbamoyl-, thiocarbamoyl-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, n- or i-propylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, n- or i-propylsulphonyl-, acetyl-, propionyl-, n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, n-, i-, s- or t-butoxycarbonyl-, propenyloxycarbonyl-, butenyloxycarbonyl-, propinyloxycarbonyl-, butinyloxycarbonyl-, aminocarbonyl-, methylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-, dimethylaminocarbonyl-, diethylaminocarbonyl-, phenylaminocarbonyl- or benzylaminocarbonyl-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, methylamino, ethylamino, n- or i-propylamino, represents dimethylamino, diethylamino, acetyl, propionyl, n- or i-butyroyl, methylcarbonyloxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, acetyloxy, propinoyloxy, n- or i-butyroyloxy, methylcarbonyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, n-, i-, s- or t-butoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, n-, i-, s- or t-butylaminocarbonyloxy, dimethylaminocarbonyloxy, diethylaminocarbonyloxy, acetylamino, propionylamino, n- or i-butyroylamino, methoxycarbonylamino, ethoxycarbonylamino, n- or i-propoxycarbonylamino, methylsulphonylamino, ethylsulphonyl amino, n- or i-propylsulphonylamino, or represents in each case optionally cyano-, carboxyl-, carbamoyl-, fluorine-, chlorine-, bromine-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, methylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-, dimethylaminocarbonyl- or diethylaminocarbonyl-substituted ethenyl, propenyl, butenyl, propenyloxy, butenyloxy, propenyloxycarbonyl, butenyloxycarbonyl, ethenecarbonyloxy, propenecarbonyloxy, butenecarbonyloxy, ethinyl, propinyl, butinyl, propinyloxy, butinyloxy, propinyloxycarbonyl, butinyloxycarbonyl, ethinecarbonyloxy, propinecarbonyloxy or butinecarbonyloxy, or represents benzoyloxy.  
 
     
     
         4 . Compounds according to any of  claims 1  to  3 , characterized in that 
 m represents 0,  
 n represents 0 or 1,  
 Q represents O (oxygen),  
 R 1  represents hydrogen, amino or methyl,  
 R 2  represents carboxyl, cyano, carbamoyl, thiocarbamoyl or represents in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, methoxycarbonyl or ethoxycarbonyl,  
 R 3  represents hydrogen, fluorine, chlorine, bromine, or represents optionally fluorine- and/or chlorine-substituted methyl,  
 R 4  represents fluorine,  
 R 5  represents cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or represents in each case optionally fluorine- and/or chlorine-substituted methyl or methoxy,  
 X represents hydroxyl, mercapto, amino, nitro, formyl, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, sulphonyl, chlorosulphonyl, represents in each case optionally cyano-, carboxyl-, carbamoyl-, thiocarbamoyl-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, acetyl-, propionyl-, n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, propenyloxycarbonyl-, methylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-, dimethylaminocarbonyl- or benzyloxycarbonyl-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl, methylamino, ethylamino, n- or i-propylamino, represents dimethylamino, diethylamino, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n-oder i-propylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, acetyloxy, propinoyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, dimethylaminocarbonyloxy, diethylaminocarbonyloxy, acetylamino, propionylamino, n- or i-butyroylamino, methoxycarbonylamino, ethoxycarbonylamino, n- or i-propoxycarbonylamino, methylsulphonylamino, ethylsulphonylamino, n- or i-propylsulphonylamino, or represents in each case optionally cyano-, carboxyl-, carbamoyl-, fluorine-, chlorine-, bromine-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, methylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-, dimethylaminocarbonyl- or diethylaminocarbonyl-substituted ethenyl, propenyl, butenyl, propenyloxy, butenyloxy, propenyloxycarbonyl, butenyloxycarbonyl, ethinyl, propinyl, butinyl, propinyloxy, butinyloxy, propinyloxycarbonyl or butinyloxycarbonyl, or represents benzoyloxy, and  
 Y represents hydroxyl, mercapto, amino, nitro, formyl, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, sulpho, chlorosulphonyl, represents in each case optionally cyano-, carboxyl-, carbamoyl-, thiocarbamoyl-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl-, ethylsulfonyl-, acetyl-, propionyl-, n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, propenyloxycarbonyl-, aminocarbonyl-, methylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-, dimethylaminocarbonyl-, phenylaminocarbonyl- or benzyloxycarbonyl-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl, methylamino, ethylamino, n-oder i-propylamino, represents dimethylamino, diethylamino, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, acetyloxy, propinoyloxy, n- or i-butyroyloxy, methylcarbonyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, dimethylaminocarbonyloxy, diethylaminocarbonyloxy, acetylamino, propionylamino, n- or i-butyroylamino, methoxycarbonylamino, ethoxycarbonylamino, n- or i-propoxycarbonylamino, methylsulphonylamino, ethylsulphonylamino, n- or i-propylsulphonylamino, or represents in each case optionally cyano-, carboxyl-, carbamoyl-, fluorine-, chlorine-, bromine-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, methylaminocarbonyl-, ethylaminocarbonyl-, n- or i-propylaminocarbonyl-, dimethylaminocarbonyl- or diethylaminocarbonyl-substituted ethenyl, propenyl, butenyl, propenyloxy, butenyloxy, propenyloxycarbonyl, butenyloxycarbonyl, ethinyl, propinyl, butinyl, propinyloxy, butinyloxy, propinyloxycarbonyl or butinyloxycarbonyl, or represents benzoyloxy.  
 
     
     
         5 . Compounds according to any of  claims 1  to  4 , characterized in that 
 R 2  represents trifluoromethyl,  
 R 3  represents hydrogen, and  
 R 5  represents cyano.  
 
     
     
         6 . Compounds according to any of  claims 1  to  5 , characterized in that 
 Q represents oxygen (O).  
 
     
     
         7 . Compounds according to any of  claims 1  to  5 , characterized in that 
 Y represents hydroxyl, methoxy, represents in each case methoxycarbonyl-, ethoxycarbonyl-, methylaminocarbonyl-, dimethylaminocarbonyl- and phenylaminocarbonyl-substituted methoxy and ethoxy, represents methylaminocarbonyloxy, methylcarbonyloxy, propinyloxy, butinyloxy and ethoxycarbonyloxy.  
 
     
     
         8 . Process for preparing compounds according to any of  claims 1  to  7 , characterized in that 
 (a) halogenophenyluracils of the general formula (II)  
                     
 in which 
 R 1 , R 2 , R 3 , R 4  and R 5  are each as defined in any of  claims 1  to  5  and  
 X 1  represents halogen,  
 
 are reacted with naphthalene derivatives of the general formula (III)  
                     
 in which 
 m, n, Q, X and Y are each as defined in any of  claims 1  to  4 ,  6  and  7 ,  
 
 or with alkali metal salts of compounds of the formula (III) 
 if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,  
 or that  
 
 (b) aminoalkenoic acid esters of the general formula (IV)  
                     
 in which 
 R 2  and R 3  are each as defined in any of  claims 1  to  5  and  
 R represents alkyl, aryl or arylalkyl,  
 
 are reacted with aryl isocyanates of the general formula (V)  
                     
 in which 
 m, n, Q, R 4 , R 5 , X and Y are each as defined in any of  claims 1  to  7   
 
 or with arylurethanes (arylcarbamates) of the general formula (VI)  
                     
 in which 
 m, n, Q, R 4 , R 5 , X and Y are each as defined in any of  claims 1  to  7  and  
 R represents alkyl, aryl or arylalkyl,  
 if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,  
 or that  
 
 (c) N-aryl-1-alkoxycarbonylamino-maleimides of the general formula (VII)  
                     
 in which 
 m, n, Q, R 3 , R 4 , R 5 , X and Y are each as defined in any of  claims 1  to  7  and  
 R′ represents alkyl  
 are reacted with a metal hydride in the presence of water and, if appropriate, in the presence of an organic solvent,  
 or that  
 
 (d) substituted phenyluracils of the general formula (Ia)  
                     
 in which 
 m, n, Q, R 2 , R 3 , R 4 , R 5 , X and Y are each as defined in any of  claims 1  to  7   
 are reacted with 1-aminooxy-2,4-dinitro-benzene or with alkylating agents of the general formula (VIII) 
 X 2 —A 1   (VIII) 
 
 in which 
 A 1  represents optionally substituted alkyl and  
 X 2  represents halogen or the grouping —O—SO 2 —O—A 1    
 if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,  
 and electrophilic or nucleophilic and/or oxidation or reduction reactions within the scope of the definition of the substituents are, if appropriate, subsequently carried out in a customary manner.  
 
 
     
     
         9 . Compounds of the general formula (Ia)  
       
         
           
           
               
               
           
         
       
       in which 
 m, n, Q, R 2 , R 3 , R 4 , R 5 , X and Y are each as defined in any of  claims 1  to  7 .  
 
     
     
         10 . Compounds of the general formula (V)  
       
         
           
           
               
               
           
         
       
       in which 
 m, n, Q, R 4 , R 5 , X and Y are each as defined in any of  claims 1  to  7 .  
 
     
     
         11 . Compounds of the general formula (VI)  
       
         
           
           
               
               
           
         
       
       in which 
 m, n, Q, R 4 , R 5 , X and Y are each as defined in any of  claims 1  to  7  and  
 R represents alkyl, aryl or arylalkyl.  
 
     
     
         12 . Compounds of the general formula (VII)  
       
         
           
           
               
               
           
         
       
       in which 
 m, n, Q, R 3 , R 4 , R 5 , X and Y are each as defined in any of  claims 1  to  7  and  
 R′ represents alkyl.  
 
     
     
         13 . Compounds of the general formula (IX)  
       
         
           
           
               
               
           
         
       
       in which 
 m, n, Q, R 4 , R 5 , X and Y are each as defined in any of  claims 1  to  7 .  
 
     
     
         14 . Herbicidal compositions, characterized in that they comprise at least one compound according to any of  claims 1  to  7  and  9  to  13  and customary extenders.  
     
     
         15 . Use of at least one compound according to any of  claims 1  to  7  and  9  to  12  for controlling undesirable plants.