Substituted phenyluracils

Abstract

Phenyluracils of the general formula (I) in which Q, R 1 , R 2 , R 3 , R 4 , R 5 and R 6 each have one of the meanings given in the description, and processes for their preparation and their use as herbicides.

1 . Substituted phenyluracils of the general formula (I)  
       
         
           
           
               
               
           
         
       
       in which 
 Q represents O (oxygen), S (sulphur), SO or SO 2 ,  
 R 1  represents hydrogen, amino, optionally cyano-, halogen- or C 1 -C 4 -alkoxy-substituted alkyl having 1 to 4 carbon atoms or in each case optionally halogen-substituted alkenyl or alkinyl having in each case 2 to 4 carbon atoms,  
 R 2  represents cyano, carboxyl, carbamoyl, thiocarbamoyl or in each case optionally cyano-, halogen- or C 1 -C 4 -alkoxy-substituted alkyl or alkoxy-carbonyl having in each case 1 to 4 carbon atoms,  
 R 3  represents hydrogen, halogen or optionally halogen-substituted alkyl having 1 to 4 carbon atoms,  
 R 4  represents hydrogen, nitro, cyano or halogen,  
 R 5  represents cyano, thiocarbamoyl, bromine or in each case optionally halogen-substituted alkyl or alkoxy having in each case 1 to 4 carbon atoms, and  
 R 6  represents an optionally nitro-, hydroxyl-, mercapto-, amino-, cyano-, carboxyl-, carbamoyl-, halogen-, C 1 -C 4 -alkyl-, cyano-C 1 -C 4 -alkyl-, carboxyl-C 1 -C 4 -alkyl-, C 1 -C 4 -halogenoalkyl-, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl-, C 1 -C 4 -alkoxy-carbonyl-C 1 -C 4 -alkyl-, C 1 -C 4 -alkylaminocarbonylalkyl-, di-(C 1 -C 4 -alkyl)-aminocarbonylalkyl-, C 1 -C 4 -alkoxy-, cyano-C 1 -C 4 -alkoxy-, C 1 -C 4 -halogenoalkoxy-, C 1 -C 4 -alkoxy-C 1 -C 4 -alkoxy-, carboxyl-C 1 -C 4 -alkoxy-, C 1 -C 4 -alkoxy-carbonyl-C 1 -C 4 -alkoxy-, C 1 -C 4 -alkylaminocarbonyl-C 1 -C 4 -alkoxy-, di-(C 1 -C 4 -alkyl)-aminocarbonyl-C 1 -C 4 -alkoxy-, C 1 -C 4 -alkoxy-carbonyl-, C 2 -C 4 -alkenyloxy-, C 2 -C 4 -alkinyloxy-, C 1 -C 4 -alkylthio-, C 1 -C 4 -halogenoalkylthio-, C 1 -C 4 -alkylsulphinyl-, C 1 -C 4 -halogenoalkylsulphinyl-, C 1 -C 4 -alkylsulphonyl-, C 1 -C 4 -halogenoalkylsulphonyl-, C 1 -C 4 -alkylcarbonyl-amino-, C 1 -C 4 -alkoxy-carbonyl-amino- or C 1 -C 4 -alkylsulphonyl-amino-substituted nitrogen-containing heterocyclic grouping from the group consisting of pyrrolyl, pyrazolyl, imidazolyl, triazolyl, triazolinyl, pyridinyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, benzoxazolyl, benzothiazolyl, quinolinyl, quinazolinyl, quinoxalinyl, 
 including all possible tautomeric forms of the compounds of the general formula (I) and the possible salts and acid or base adducts of the compounds of the general formula (I).  
 
 
     
     
         2 . Compounds according to  claim 1 , characterized in that 
 Q represents O (oxygen), S (sulphur) or SO 2 ,    R 1  represents hydrogen, amino, in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, or in each case optionally fluorine- and/or chlorine-substituted propenyl or propinyl,    R 2  represents cyano, carboxyl, carbamoyl, thiocarbamoyl or 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 in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, n- or i-propyl,    R 4  represents hydrogen, cyano, fluorine, chlorine or bromine,    R 5  represents cyano, thiocarbamoyl, bromine or in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, methoxy or ethoxy, and    R 6  represents an in each case optionally nitro-, hydroxyl-, amino-, cyano-, carboxyl-, carbamoyl-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, chloromethyl-, fluoromethyl-, dichloromethyl-, difluoromethyl-, trichloromethyl-, trifluoromethyl-, chlorodifluoromethyl-, fluorodichloromethyl-, chloroethyl-, fluoroethyl-, dichloroethyl-, difluoroethyl, chlorofluoroethyl-, trichloroethyl-, trifluoroethyl-, chlorodifluoroethyl-, fluorodichloroethyl-, tetrafluoroethyl-, chlorotrifluoroethyl-, pentafluoroethyl-, chloro-n-propyl-, fluoro-n-propyl-, chloro-1-propyl-, fluoro-1-propyl-, dichloropropyl-, difluoropropyl-, trichloropropyl-, trifluoropropyl-, cyanomethyl-, cyanoethyl-, cyanopropyl-, carboxymethyl-, carboxyethyl-, carboxypropyl-, methoxymethyl-, ethoxymethyl-, propoxymethyl-, methoxyethyl-, ethoxyethyl-, methoxycarbonylmethyl-, ethoxycarbonylmethyl-, n- or i-propoxycarbonylmethyl-, methylaminocarbonylmethyl-, ethylaminocarbonylmethyl-, dimethylaminocarbonylmethyl-, methoxycarbonylethyl-, ethoxycarbonylethyl-, n- or i-propoxycarbonylethyl-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s- or t-butoxy-, difluoromethoxy-, trifluoromethoxy-, chlorodifluoromethoxy-, carboxymethoxy-, carboxyethoxy-, methoxycarbonylmethoxy-, ethoxycarbonylmethoxy-, n- or i-propoxycarbonylmethoxy-, methylaminocarbonylmethoxy-, ethylaminocarbonylmethoxy-, dimethylaminocarbonylmethoxy-, methoxycarbonylethoxy-, ethoxycarbonylethoxy-, n- or i-propoxycarbonylethoxy-, methylaminocarbonylethoxy-, ethylaminocarbonylethoxy-, dimethylaminocarbonylethoxy-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-, propenyloxy-, butenyloxy-, propinyloxy-, butinyloxy-, methylthio-, ethylthio-, n- or i-propylthio-, n-, i-, s- or t-butylthio-, difluoromethylthio-, trifluoromethylthio-, chlorodifluoromethylthio-, methylsulphinyl-, ethylsulphinyl-, n- or i-propylsulphinyl-, trifluoromethylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, n- or i-propylsulfonyl-, trifluoromethylsulphonyl-, acetylamino-, propionylamino-, n- or i-butyroylamino-, methoxycarbonylamino-, ethoxycarbonylamino-, n- or i-propoxycarbonylamino-, methylsulphonylamino-, ethylsulphonylamino-, n- or i-propylsulphonylamino-substituted nitrogen-containing heterocyclic grouping form the group consisting of pyrrolyl, pyrazolyl, imidazolyl, triazolyl, triazolinyl, pyridinyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, benzoxazolyl, benzothiazolyl, quinolinyl, quinazolinyl, quinoxalinyl.    
     
     
         3 . Compounds according to  claim 1  or  2 , characterized in that 
 Q represents O (oxygen) or S (sulphur),  
 R 1  represents hydrogen, amino or represents in each case optionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl or ethyl,  
 R 2  represents cyano, carboxyl, carbamoyl or in each case optionally fluorine- and/or chlorine-substituted methyl, ethyl, methoxycarbonyl or ethoxycarbonyl,  
 R 3  represents hydrogen, fluorine, chlorine, bromine or in each case optionally fluorine- and/or chlorine-substituted methyl or ethyl,  
 R 4  represents hydrogen, fluorine or chlorine,  
 R 5  represents cyano, thiocarbamoyl, bromine or trifluoromethyl, and  
 R 6  represents an in each case optionally nitro-, hydroxyl-, amino-, cyano-, carboxyl-, carbamoyl-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, dichloromethyl-, difluoromethyl-, trichloromethyl-, trifluoromethyl-, chlorodifluoromethyl-, fluorodichloromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s- or t-butoxy-, difluoromethoxy-, trifluoromethoxy-, chlorodifluoromethoxy-, carboxymethoxy-, carboxyethoxy-, methoxycarbonylmethoxy-, ethoxycarbonylmethoxy-, n- or i-propoxycarbonylmethoxy-, methoxycarbonylethoxy-, ethoxycarbonylethoxy-, n- or i-propoxycarbonylethoxy-, methoxycarbonyl-, ethoxycarbonyl-, propenyloxy-, butenyloxy-, propinyloxy-, butinyloxy-, methylthio-, ethylthio-, n- or i-propylthio-, n-, i-, s- or t-butylthio-, difluoromethylthio-, trifluoromethylthio-, chlorodifluoromethylthio-, methylsulphinyl-, ethylsulphinyl-, n- or i-propylsulphinyl-, trifluoromethylsulphinyl-, methylsulphonyl, ethylsulphonyl-, n- or i-propylsulphonyl-, trifluoromethylsulphonyl-, acetylamino-, propionylamino-, n- or i-butyroylamino-, methoxycarbonylamino-, ethoxycarbonylamino-, n- or i-propoxycarbonylamino-, methylsulphonylamino-, ethylsulphonylamino-, n- or i-propylsulphonylamino-substituted nitrogen-containing heterocyclic grouping from the group consisting of pyrrolyl, pyrazolyl, imidazolyl, triazolyl; triazolinyl, pyridinyl, pyrazinyl, pyridazinyl, pyrimidinyl, triazinyl, benzoxazolyl, benzothiazolyl, quinolinyl, quinazolinyl, quinoxalinyl.  
 
     
     
         4 . Compounds according to any of  claims 1  to  3 , characterized in that 
 R 1  represents hydrogen, amino, methyl or ethyl,  
 R 2  represents cyano or trifluoromethyl,  
 R 3  represents hydrogen, chlorine or methyl,  
 R 5  represents cyano, thiocarbamoyl or bromine, and  
 R 6  represents in each case optionally hydroxyl-, amino-, cyano-, carboxyl-, carbamoyl-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, dichloromethyl-, difluoromethyl-, trichloromethyl-, trifluoromethyl-, chlorodifluoromethyl-, fluorodichloromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy-, trifluoromethoxy-, chlorodifluoromethoxy-, carboxymethoxy-, carboxyethoxy-, methoxycarbonylmethoxy-, ethoxycarbonylmethoxy-, n- or i-propoxycarbonylmethoxy-, methoxycarbonylethoxy-, ethoxycarbonylethoxy-, n- or i-propoxycarbonylethoxy-, methoxycarbonyl-, ethoxycarbonyl-, propenyloxy-, butenyloxy-, propinyloxy-, butinyloxy-, methylthio-, ethylthio-, n- or i-propylthio-, difluoromethylthio-, trifluoromethylthio-, chlorodifluoromethylthio-, methylsulphinyl-, ethylsulphinyl-, n- or i-propylsulphinyl-, trifluoromethylsulphinyl-, methylsulphonyl-, ethylsulphonyl-, n- or i-propylsulfonyl-, trifluoromethylsulphonyl-, acetylamino-, propionylamino-, n- or i-butyroylamino-, methoxycarbonylamino-, ethoxycarbonylamino-, n- or i-propoxycarbonylamino-, methylsulphonylamino-, ethylsulphonylamino-, n- or i-propylsulphonylamino-substituted pyrazolyl, pyridinyl, pyrimidinyl, triazinyl or benzoxazolyl.  
 
     
     
         5 . Compounds according to any of  claims 1  to  4 , characterized in that 
 R 1  represents hydrogen, amino or methyl,  
 R 2  represents trifluoromethyl,  
 R 5  represents cyano or bromine, and  
 R 6  represents in each case optionally hydroxyl-, amino-, cyano-, fluorine-, chlorine-, methyl-, ethyl-, trichloromethyl-, methoxy- or ethoxy-substituted pyrazolyl, pyridinyl, pyrimidinyl or benzoxazolyl.  
 
     
     
         6 . Compounds according to any of  claims 1  to  5 , characaterized in that 
 Q represents O (oxygen).  
 
     
     
         7 . Process for preparing compounds according to any of  claims 1  to  6 , characterized in that 
 (a) phenyluracils of the general formula (II)  
                     
  in which 
 Q, R 1 , R 2 , R 3 , R 4  and R 5  are each as defined in any of  claims 1  to  6   
 are reacted with compounds of the general formula (III)  
 X 1 —R 6   (III)  
  in which 
 R 6  is as defined in any of  claims 1  to  5  and  
 X 1  represents halogen or alkylsulphonyl,  
 if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,  
 or that  
 
 
 (b) halogenophenyluracils of the general formula (IV)  
                     
  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 2  represents halogen  
 are reacted with compounds of the general formula (V)  
 M-Q-R 6   (V)  
 in which 
 Q and R 6  are each as defined in any of  claims 1  to  6  and  
 M represents hydrogen or a metal equivalent,  
 if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,  
 or that  
 
 
 (c) aminoalkenoic acid esters of the general formula (VI)  
                     
  in which 
 R 1 , 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 substituted phenyl isocyanates of the general formula (VII)  
                     
  in which 
 Q, R 4 , R 5  and R 6  are each as defined in any of  claims 1  to  6   
 or with substituted phenylurethanes (phenylcarbamates) of the general formula (VIII)  
                     
  in which 
 Q, R 4 , R 5  and R 6  are each as defined in any of  claims 1  to  6  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  
 
 
 
 (d) substituted N-phenyl-1-alkoxycarbonylamino-maleimides of the general formula (IX)  
                     
  in which 
 Q, R 4 , R 5  and R 6  are each as defined in any of  claims 1  to  6  and  
 R′ represents alkyl  
 are reacted with a metal hydroxide in the presence of water and, if appropriate in the presence of an organic solvent,  
 or that  
 
 (e) substituted phenyluracils of the general formula (Ia)  
                     
  in which 
 Q, R 2 , R 3 , R 4 , R 5  and R 6  are each as defined in any of  claims 1  to  6   
 are reacted with 1-aminooxy-2,4-dinitro-benzene or 2-aminooxysulphonyl-1,3,5-trimethylbenzene or with alkylating agents of the general formula (X)  
 X 3 -A 1   (X)  
  in which 
 A 1  represents optionally cyano-, halogen- or C 1 -C 4 -alkoxy-substituted alkyl having 1 to 4 carbon atoms or in each case optionally halogen-substituted alkenyl or alkinyl having in each case 2 to 4 carbon atoms, and  
 X 3  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.  
 
 
 
     
     
         8 . Compounds of the formula (VII)  
       
         
           
           
               
               
           
         
       
       in which 
 Q, R 4 , R 5  and R 6  are each as defined in any of  claims 1  to  6 .  
 
     
     
         9 . Process for preparing compounds according to  claim 8 , characterized in that aniline derivatives of the general formula (XI)  
       
         
           
           
               
               
           
         
       
       in which 
 Q, R 4 , R 5  and R 6  are each as defined in any of  claims 1  to  6   
 are reacted with phosgene in the presence of a diluent, such as, for example, chlorobenzene, at temperatures between −20° C. and +150° C.  
 
     
     
         10 . Compounds of the formula (VIII)  
       
         
           
           
               
               
           
         
       
       in which 
 Q, R 4 , R 5 , R 6  and R are each as defined in any of  claims 1  to  7 .  
 
     
     
         11 . Process for preparing compounds according to  claim 10 , characterized in that aniline derivatives of the general formula (XI)  
       
         
           
           
               
               
           
         
       
       in which 
 Q, R 4 , R 5  and R 6  are each as defined in any of  claims 1  to  6   
 are reacted with chlorocarbonyl compounds of the general formula (XII)  
 RO—CO—Cl  (XII)  
  in which 
 R represents alkyl, aryl or arylalkyl,  
 if appropriate in the presence of an acid acceptor, such as, for example, pyridine, and if appropriate in the presence of a diluent, such as, for example, methylene chloride, at temperatures between −20° C. and +100° C.  
 
 
     
     
         12 . Compounds of the formula (XIa)  
       
         
           
           
               
               
           
         
       
       in which 
 Q, R 4  and R 6  are each as defined in any of  claims 1  to  6  and  
 Y represents cyano, thiocarbamoyl or trifluorormethyl.  
 
     
     
         13 . Process for preparing compounds according to  claim 12 , characterized in that 
 (α) anilines of the general formula (XIII)                           in which 
 Q, R 4  and Y are each as defined in any of  claims 1  to  6  and  12   
 are reacted with compounds of the general formula (III)  
 X 1 —R 6   (III)  
  in which 
 R 6  and X 1  are each as defined in any of  claims 1  to  5  and  7 ,  
 if appropriate in the presence of an acid acceptor, such as, for example, potassium hydroxide, potassium carbonate or pyridine, and if appropriate in the presence of a diluent, at temperatures between 0° C. and 200° C.,  
 or that  
 
   (β) anilines of the general formula (XIV)                           in which 
 R 4 , X 2  and Y are each as defined in any of  claims 1  to  5 ,  7  and  12   
 are reacted with compounds of the general (V)  
 M-Q-R 6   (V)  
  in which 
 M, Q and R 6  are each as defined in any of  claims 1  to  7 ,  
 if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent, at temperatures between 0° C. and 200° C.  
 
   
     
     
         14 . Compounds of the formula (IX)  
       
         
           
           
               
               
           
         
       
       in which 
 Q, R 4 , R 5  and R 6  are each as defined in any of  claims 1  to  6  and R′ represents alkyl.  
 
     
     
         15 . Process for preparing compounds according to  claim 14 , characterized in that alkyl (2,5-di oxo-2,5-dihydro-furan-3-yl)-carbamates of the general formula  
       
         
           
           
               
               
           
         
       
       in which 
 R 3  is as defined in any of  claims 1  to  5  and  
 R′ represents alkyl  
 are reacted with aniline derivatives of the general formula (XI)  
                     
  in which 
 Q, R 4 , R 5  and R 6  are each as defined in any of  claims 1  to  6 ,  
 if appropriate in the presence of a diluent, at temperatures between 0° C. and 200° C.  
 
 
     
     
         16 . Compounds of the formula (Ia)  
       
         
           
           
               
               
           
         
       
       in which 
 Q, R 2 , R 3 , R 4 , R 5  and R 6  are each as defined in any of  claims 1  to  6 .  
 
     
     
         17 . Herbicidal compositions, characterized in that they comprise at least one compound according to any of  claims 1  to  6  and customary extenders.  
     
     
         18 . Use of at least one compound according to any of  claims 1  to  6  or a composition according to  claim 17  for controlling undesirable plants.