Herbicidally and insecticidally active phenyl-substituted pyridazinones

Abstract

The invention describes phenyl-substituted pyridazinones of the formula (I) as herbicides and insecticides. In this formula (I), A, B, G, X, Y and Z are radicals such as hydrogen, organic radicals such as alkyl, and other radicals such as halogen, nitro and cyano.

1 . A 4-phenylpyridazinone of the formula (I) or salts thereof 
       
         
           
           
               
               
           
         
       
       in which
 A and B are in each case independently of one another hydrogen, (C 3 -C 6 )-cycloalkyl or (C 1 -C 6 )-alkyl substituted by n radicals from the group consisting of halogen, (C 3 -C 6 )-cycloalkyl, phenyl and halophenyl, 
 n is 0, 1, 2 or 3; 
 G is R 8 ; 
 R 8  is (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl, (C 1 -C 4 )-alkoxy-(C 1 -C 6 )-alkyl, (C 1 -C 4 )-alkylthio-(C 1 -C 4 )-alkyl or di-(C 1 -C 4 )-alkoxy-(C 1 -C 6 )-alkyl substituted by n halogen atoms, (C 3 -C 6 )-cycloalkyl substituted by n radicals from the group consisting of halogen, (C 1 -C 4 )-alkyl and (C 1 -C 4 )-alkoxy, 
 a fully saturated 3- to 6-membered ring consisting of 3 to 5 carbon atoms and 1 to 3 heteroatoms from the group consisting of oxygen, sulfur and nitrogen which is substituted by n radicals from the group consisting of halogen, (C 1 -C 4 )-alkyl and (C 1 -C 4 )-alkoxy, 
 phenyl, phenyl-(C 1 -C 4 )-alkyl, heteroaryl, phenoxy-(C 1 -C 4 )-alkyl or heteroaryloxy-(C 1 -C 4 )-alkyl substituted by n radicals from the group consisting of halogen, (C 1 -C 4 )-alkyl and (C 1 -C 4 )-alkoxy; 
 and 
 a) X is hydrogen, (C 1 -C 6 )-alkyl or (C 3 -C 6 )-cycloalkyl;
 Y is halogen, cyano, nitro, halo-(C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkoxy, (C 3 -C 6 )-cycloalkyl, (C 1 -C 6 )-alkoxy or is phenyl which is substituted by n halogen atoms, 
 Z is hydrogen, halogen, cyano, nitro, (C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkoxy, (C 3 -C 6 )-cycloalkyl or is phenyl which is substituted by n halogen atoms; 
 or 
 
 b) X is halogen, cyano, nitro or is (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 1 -C 6 )-alkoxy or phenyl, each of which is substituted by n halogen atoms;
 Y and Z are each independently of one another hydrogen, halogen, cyano, nitro, (C 3 -C 6 )-cycloalkyl or are (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy or phenyl, each of which is substituted by n halogen atoms. 
 
 
     
     
         2 . The 4-phenylpyridazinone as claimed in  claim 1  in which
 A is hydrogen, (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, benzyl or halophenyl-(C 1 -C 6 )-alkyl; 
 B is hydrogen, (C 1 -C 6 )-alkyl, (C 3 -C 6 )-cycloalkyl, (C 3 -C 6 )-cycloalkyl-(C 1 -C 6 )-alkyl, benzyl or halophenyl-(C 1 -C 6 )-alkyl; 
 n is 0, 1, 2 or 3; 
 G is R 8 ; 
 R 8  is (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl substituted by n halogen atoms or is phenyl or phenyl-(C 1 -C 4 )-alkyl substituted by n radicals from the group consisting of halogen, (C 1 -C 4 )-alkyl and (C 1 -C 4 )-alkoxy; 
 and 
 a) X is hydrogen, methyl, ethyl or cyclopropyl;
 Y is halogen, cyano, nitro, halo-(C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkoxy, (C 3 -C 6 )-cycloalkyl, (C 1 -C 6 )-alkoxy or phenyl which is substituted by n halogen atoms, 
 Z is hydrogen, halogen, halo-(C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkoxy, (C 3 -C 6 )-cycloalkyl or phenyl which is substituted by n halogen atoms, 
 or 
 
 b) X is halogen, cyano, nitro, halo-(C 1 -C 6 )-alkyl, halo-(C 1 -C 6 )-alkoxy, (C 1 -C 6 )-alkoxy or (C 3 -C 6 )-cycloalkyl;
 Y is hydrogen, halogen, cyano, nitro, (C 3 -C 6 )-cycloalkyl, is (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy or phenyl, each of which is substituted by n halogen atoms; 
 Z is hydrogen, halogen, cyano, nitro, (C 3 -C 6 )-cycloalkyl or is (C 1 -C 6 )-alkyl, (C 1 -C 6 )-alkoxy or phenyl, each of which is substituted by n halogen atoms. 
 
 
     
     
         3 . The 4-phenylpyridazinone as claimed in  claim 1  in which
 A is hydrogen, methyl, ethyl, isobutyl, cyclopropyl, cyclopropylmethyl, benzyl, 2-chlorophenylmethyl, 3-chlorophenylmethyl or 4-chlorophenylmethyl; 
 B is hydrogen, methyl, ethyl, isobutyl, tert-butyl, cyclopropyl, cyclopropylmethyl, benzyl, 2-chlorophenylmethyl, 3-chlorophenylmethyl or 4-chlorophenylmethyl, 
 n is 0, 1, 2 or 3; 
 G is R 8 ; 
 R 8  is (C 1 -C 6 )-alkyl, (C 2 -C 6 )-alkenyl, (C 2 -C 6 )-alkynyl or is benzyl substituted by n radicals from the group consisting of halogen, (C 1 -C 4 )-alkyl and (C 1 -C 4 )-alkoxy; 
 and 
 a) X is hydrogen, methyl or ethyl;
 Y is fluorine, bromine, chlorine, iodine, cyano, nitro, cyclopropyl, methoxy, ethoxy, trifluoromethyl or trifluoromethoxy, phenyl or halophenyl; 
 Z is hydrogen, fluorine, bromine, chlorine, iodine, methyl, ethyl, methoxy, ethoxy, trifluoromethyl or cyclopropyl; 
 or 
 
 b) X is fluorine, bromine, chlorine, iodine, cyano, nitro, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy or cyclopropyl;
 Y is hydrogen, fluorine, bromine, chlorine, iodine, methyl, ethyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy or cyclopropyl; 
 Z is hydrogen, fluorine, bromine, chlorine, iodine, methyl, ethyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy, cyclopropyl, chlorophenyl or fluorophenyl. 
 
 
     
     
         4 . A herbicidal composition which comprises an effective amount of at least one 4-phenylpyridazinone of the formula (I) as claimed in  claim 1 . 
     
     
         5 . The herbicidal composition as claimed in  claim 4  as a mixture with formulation auxiliaries. 
     
     
         6 . The herbicidal composition as claimed in  claim 4  which comprises at least one further pesticidally active compound from the group consisting of insecticides, acaricides, herbicides, fungicides, safeners and growth regulators. 
     
     
         7 . The herbicidal composition as claimed in  claim 4  which comprises a safener. 
     
     
         8 . The herbicidal composition as claimed in  claim 4  which comprises a further herbicide. 
     
     
         9 . A method for controlling unwanted plants wherein an effective amount of at least one 4-phenylpyridazinone of the formula (I) as claimed in  claim 1  is applied to the plants or to the site where the unwanted plants are growing. 
     
     
         10 . A method of use of a 4-phenylpyridazinone of the formula (I) as claimed in  claim 1  for controlling unwanted plants. 
     
     
         11 . The method as claimed in  claim 10  wherein the 4-phenylpyridazinone of the formula (I) is used for controlling unwanted plants in crops of useful plants. 
     
     
         12 . The method as claimed in  claim 11  wherein the useful plants are transgenic useful plants. 
     
     
         13 . A compound of the formula (II), 
       
         
           
           
               
               
           
         
       
       in which the substituents A, B, X, Y and Z are as defined in  claim 1  and R 9  is (C 1 -C 6 )-alkyl. 
     
     
         14 . A compound of the formula (IIa) 
       
         
           
           
               
               
           
         
       
       in which the substituents B, X, Y and Z are as defined in  claim 1 . 
     
     
         15 . A 4-phenylpyridazinone of the formula (I) as claimed in  claim 1  capable of use as an insecticide.