Substituted 1-arylpyrazoles

Abstract

The invention relates to new substituted 1-arylpyrazoles of the general formula (I)to a plurality of processes for their preparation, and to their use as pesticides.

What is claimed is:  
     
       1. A substituted 1-arylpyrazole of the formula                    
       wherein 
       R 1  represents hydrogen, cyano, alkyl, alkoxyalkyl, alkylthioalkyl, halogenoalkyl or cyanoalkyl,  
       R 2  represents difluoroethyl or trifluoroethyl,  
       R 3  represents hydrogen, amino, halogen or one of the following groups                    
       in which 
       R 4  represents alkyl, halogenoalkyl, alkoxyalkyl or optionally substituted phenyl,  
       R 5  represents hydrogen or alkyl,  
       R 6  represents hydrogen, alkyl or optionally substituted phenyl, and  
       R 7  represents alkyl, or  
       R 5  and R 6  together with the carbon atom to which they are bonded represent an optionally substituted heterocycle,  
       Ar represents optionally substituted pyridyl, and  
       n represents a number 0, 1 or 2.  
     
     
       2. A substituted 1-arylpyrazole according to  claim 1 , wherein 
       R 1  represents hydrogen, cyano, (C 1 -C 6 )-alkyl, (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-halogenoalkyl or (C 1 -C 2 )-cyanoalkyl,  
       R 2  represents difluoroethyl or trifluoroethyl,  
       R 3  represents hydrogen, amino, halogen or one of the following groups                    
       wherein 
       R 4  represents (C 1 -C 6 )-alkyl, (C 1 -C 6 )-halogenoalkyl having 1-3 halogen atoms, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, or phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents,  
       R 5  represents hydrogen or (C 1 -C 6 )-alkyl,  
       R 6  represents hydrogen, (C 1 -C 6 )-alkyl, or phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents,  
       R 7  represents (C 1 -C 6 )-alkyl or  
       R 5  and R 6  together with the carbon atom to which they are bonded represent optionally substituted pyridyl,  
       Ar represents pyridyl optionally monosubstituted to trisubstituted by identical or different substituents selected from the series comprising  group consisting of halogen, halogeno (C 1 -C 6 )alkyl, halogeno(C 1 -C 6 )alkylthio, halogeno(C 1 -C 6 )alkoxy, alkoxy, hydrazino, (C 1 -C 6 )-dialkylhydrazino, amino, amino (C 1 -C 6 )alkyl, diamino(C 1 -C 6 )alkyl, imino(C 1 -C 6 )alkyl, cyano, (C 1 -C 6 )alkylthio or  and the group                    
       in which 
       R 9  and R 10  are identical or different and represent hydrogen or (C 1 -C 6 )-alkyl, and  
       n represents a number 0, 1 or 2.  
     
     
       3. A substituted 1-arylpyrazole according to  claim 1 , wherein 
       R 1  represents hydrogen, cyano, (C 1 -C 4 )-alkyl, (C 1 -C 4 )-alkoxy-(C 1 -C 2 )-alkyl, (C 1 -C 2 )-halogenoalkyl having 1 to 5 identical or different fluorine, chlorine or bromine atoms, or cyanomethyl,  
       R 2  represents difluoroethyl or trifluoroethyl,  
       R 3  represents hydrogen, amino, bromine or one of the following groups                    
       wherein 
       R 4  represents (C 1 -C 4 )-alkyl, (C 1 -C 4 )-halogenoalkyl having 1-3 halogen atoms, (C 1 -C 4 )-alkoxy-(C 1 -C 2 )alkyl, or phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents,  
       R 5  represents hydrogen or (C 1 -C 4 )-alkyl,  
       R 6  represents hydrogen, (C 1 -C 4 )-alkyl, phenyl which is optionally monosubstituted or disubstituted by identical or different substituents, or 4-hydroxy-3-methoxy-phenyl,  
       R 7  represents (C 1 -C 4 )-alkyl, or  
       R 5  and R 6  together with the carbon atom to which they are bonded represent optionally substituted pyridyl,  
       Ar represents pyridyl optionally monosubstituted to trisubstituted by identical or different substituents selected from the series comprising  group consisting of fluorine, chlorine, trifluoromethyl, trifluoromethylthio, trifluoromethoxy, methoxy, hydrazino, dimethylhydrazino, amino, methylamino, dimethylamino, iminomethyl, cyano, methylthio or  and the group                    
       in which 
       R 9  and R 10  are identical or different and represent hydrogen or (C 1 -C 4 )-alkyl, and  
       n represents a number 0, 1 or 2.  
     
     
       4. A substituted 1-arylpyrazole according to  claim 1 , wherein 
       R 1  represents hydrogen, cyano, (C 1 -C 4 )-alkyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, trifluoromethyl, bromomethyl and cyanomethyl,  
       R 2  represents 1,1-difluoroethyl or 2,2,2-trifluoroethyl,  
       R 3  represents halogen, amino, bromine or one of the following groups                    
       wherein 
       R 4  represents (C 1 -C 4 )-alkyl, (C 1 -C 4 )-halogenoalkyl having 1-3 halogen atoms, (C 1 -C 4 )-alkoxy-(C 1 -C 2 )alkyl, or phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents,  
       R 5  represents hydrogen or (C 1 -C 4 )-alkyl,  
       R 6  represents hydrogen, (C 1 -C 4 )-alkyl, phenyl which is optionally monosubstituted or disubstituted by identical or different substituents, or 4-hydroxy-3-methoxy-phenyl,  
       R 7  represents (C 1 -C 4 )-alkyl, or  
       R 5  and R 6  together with the carbon atom to which they are bonded represent optionally substituted pyridyl,  
       Ar represents a 2-pyridyl radical which is substituted in the 4-position by trifluoromethyl and in the 6-position by fluorine or chlorine, and  
       n represents a number 0, 1 or 2.  
     
     
       5. A compound according to  claim 1 , wherein R 3  is amino. 
     
     
       6. A compound according to  claim 1 , wherein 
       Ar represents a 2-pyridyl radical which is substituted in the 4-position by trifluoromethyl and in the 6-position by fluorine or chlorine.  
     
     
       7. A compound according to  claim 1 , wherein such compound is 5-amino-3-methyl-4-(1,1-difluoroethylthio)-1-(3-chloro-5-trifluoromethlpyrid-2-yl)-pyrazole of the formula                    
     
     
       8. An insecticidal composition comprising an insecticidally effective amount of a compound according to  claim 1  and a diluent. 
     
     
       9. A method of combating unwanted insects which comprises administering to such insects or to a locus from which it is desired to exclude such insects an insecticidally effective amount of a compound according to  claim 1 . 
     
     
       10. A substituted 1-arylpyrazole of the formula                    
       wherein 
       n represents  0 ,  1  or  2   
       R 1  represents hydrogen, cyano, alkyl, alkoxyalkyl, alkylthioalkyl, halogenoalkyl or cyanoalkyl,  
       R 2  represents difluoroethyl or trifluoroethyl,  
       R 3  represents hydrogen, amino, halogen or one of the following groups                    
       in which 
       R 4  represents alkyl, halogenoalkyl, alkoxyalkyl or optionally substituted phenyl,  
       R 5  represents hydrogen or alkyl,  
       R 6  represents hydrogen, alkyl or optionally substituted phenyl, and  
       R 7  represents alkyl, or  
       R 5  and R 6  together with the carbon atom to which they are bonded represent an optionally substituted heterocycle,  
       Ar represents phenyl which is trisubstituted by identical or different substituents,  substituents in the  2 - ,  4   -  and  6   - positions, substituents in  the 2-position being fluorine or chlorine, in the 4-position trifluoromethyl and in the 6-position fluorine or chlorine.  
     
     
       11. A compound according to  claim 10 , wherein 
       R 1  represents hydrogen, cyano, (C 1 -C 6 )-alkyl, (C 1 -C 4 )-alkoxy-(C 1 -C 4 )-alkyl, (C 1 -C 4 )-halogenoalkyl or (C 1 -C 2 )-cyanoalkyl,  
       R 2  represents difluoroethyl or trifluoroethyl,  
       R 3  represents hydrogen, amino, halogen or one of the following groups                    
       wherein 
       R 4  represents (C 1 -C 6 )-alkyl, (C 1 -C 6 )-halogenoalkyl having 1-3 halogen atoms, (C 1 -C 6 )-alkoxy-(C 1 -C 6 )-alkyl, or phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents,  
       R 5  represents hydrogen or (C 1 -C 6 )-alkyl,  
       R 6  represents hydrogen, (C 1 -C 6 )-alkyl, or phenyl which is optionally monosubstituted to trisubstituted by identical or different substituents,  
       R 7  represents (C 1 -C 6 )-alkyl or  
       R 5  and R 6  together with the carbon atom to which they are bonded represent optionally substituted pyridyl.  
     
     
       12. A compound according to  claim 10 , wherein R 3  is amino. 
     
     
       13. A compound according to  claim 10 , wherein such compound is 5-amino-3-methyl-4-(1,1-difluoroethylthio)-1-(2,6-dichloro-4-trifluorometh ylphenyl)-pyrazole of the formula                    
     
     
       14. A compound according to  claim 10 , wherein such compound is 5-amino-3-cyano-4-(1,1-difluoroethylthio)-1-(2,6-dichloro-4-trifluoromethy lphenyl)-pyrazole of the formula                    
     
     
       15. A compound according to  claim 10 , wherein such compound is 5-amino-4-(1,1-difluoroethylthio)-1-(2,6-dichloro-4-trifluoromethylphenyl)-pyrazole of the formula                    
     
     
       16. A compound according to  claim 10 , wherein such compound is 5-amino-3-cyano-4-(1,1-difluoroethylthio))-1-(2,4,6-trichlorophenyl)-pyrazole of the formula                    
         5 - amino -   3   - cyano -   4   -(   1 , 1   - difluoroethylsulfonyl )-   1   -(   2 , 6   - dichloro -   4   - trifluoromethylphenyl )- pyrazole of the formula                      
         
     
     
       17. An insecticidal composition comprising an insecticidally effective amount of a compound according to  claim 10  and a diluent. 
     
     
       18. A method of combating unwanted insects which comprises administering to such insects or to a locus from which it is desired to exclude such insects an insecticidally effective amount of a compound according to  claim 10 . 
     
     
       19. The method according to  claim 18  wherein such compound is 5-amino-3-methyl-4-(1,1-difluorothylthio)-1-(2,6-dichloro-4-trifluoromethylphenyl)-pyrazole, 5-amino-3-cyano-4-(1,1-difluoroethylthio)-1-(2,6-dichloro-4-trifluoromethylphenyl)-pyrazole, 5-amino-4-(1,1-difluoroethylthio)-1-(2,6-dichloro-4-trifluoromethylphenyl)-pyrazole, or 5-amino-3-cyano-4-(1,1-difluoroethylthio))-1-(2,4,6-trichlorophenyl)-pyrazole. 
     
     
       20. A compound according to  claim 10 , of the formula