Thiazoyl biphenyl amides

Abstract

The invention relates to novel thiazolylbiphenylamides of the formula (I) in which R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are as defined in the disclosure, to a process for preparing these compounds and to their use for controlling unwanted microorganisms.

1 - 17 . (canceled)  
   
   
       18 . A thiazolylbiphenylamide of the formula (I)  
     
       
         
         
             
             
         
       
       in which  
       R 1 , R 2 , and R 3  independently of one another represent hydrogen, halogen, cyano, nitro, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkyl-sulfonyl, or C 3 -C 6 -cycloalkyl; or represent C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkylthio, or C 1 -C 4 -haloalkylsulfonyl having in each case 1 to 5 halogen atoms, or  
       R 1  and R 2  together or R 2  and R 3  together represent optionally halogen- or C 1 -C 6 -alkyl-substituted alkenylene,  
       R 4  and R 5  independently of one another represent hydrogen, halogen, cyano, nitro, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfonyl, or C 3 -C 6 -cycloalkyl; or represent C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkylthio, or C 1 -C 4 -haloalkylsulfonyl having in each case 1 to 5 halogen atoms, or  
       R 6  represents C 1 -C 8 -alkyl, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 8 -cycloalkyl; represents C 1 -C 6 -haloalkyl, C 1 -C 4 -haloalkylsulfanyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -haloalkylsulfonyl, halo-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, or C 3 -C 8 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine, and/or bromine atoms; or represents —COR 7 , —CONR 8 R 9 , or —CH 2 NR 10 R 11 ,  
       R 7  represents hydrogen, C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 3 -C 8 -cycloalkyl; represents C 1 -C 6 -haloalkyl, C 1 -C 6 -haloalkoxy, halo-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, or C 3 -C 8 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine, and/or bromine atoms; or represents 4-(difluoromethyl)-2-methyl-1,3-thiazol-2-yl,  
       R 8  and R 9  independently of one another represent hydrogen, C 1 -C 8 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, or C 3 -C 8 -cycloalkyl; or represent C 1 -C 8 -haloalkyl, halo-C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, or C 3 -C 8 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine, and/or bromine atoms, or  
       R 8  and R 9  together with the nitrogen atom to which they are attached form a saturated heterocycle that is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen and C 1 -C 4 -alkyl and that has 5 to 8 ring atoms, where the heterocycle optionally contains 1 or 2 further non-adjacent heteroatoms selected from the group consisting of oxygen, sulfur, and NR 12 ,  
       R 10  and R 11  independently of one another represent hydrogen, C 1 -C 8 -alkyl, or C 3 -C 8 -cycloalkyl; or represent C 1 -C 8 -haloalkyl or C 3 -C 8 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine, and/or bromine atoms, or  
       R 10  and R 11  together with the nitrogen atom to which they are attached form a saturated heterocycle that is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen and C 1 -C 4 -alkyl and that has 5 to 8 ring atoms, where the heterocycle optionally contains 1 or 2 further non-adjacent heteroatoms from the group consisting of oxygen, sulfur and NR 12 , and  
       R 12  represents hydrogen or C 1 -C 6 -alkyl.  
     
   
   
       19 . A thiazolylbiphenylamide of formula (I) as claimed in  claim 18  in which 
 R 1 , R 2 , and R 3  independently of one another represent hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or isopropyl, n-, iso-, sec-, or tert-butyl, methoxy, ethoxy, methylthio, ethylthio, n- or isopropylthio, cyclopropyl, trifluoromethyl, trichloromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, or trifluoromethylthio, or    R 1  and R 2  or R 2  and R 3  together represent optionally fluorine-, chlorine-, bromine-, or methyl-substituted butadienediyl,    R 4  and R 5  independently of one another represent hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or isopropyl, n-, iso-, sec-, or tert-butyl, methoxy, ethoxy, methylthio, ethylthio, n- or isopropylthio, cyclopropyl, trifluoromethyl, trichloromethyl, trifluoroethyl, difluoromethoxy, trifluoromethoxy, difluorochloromethoxy, trifluoroethoxy, difluoromethylthio, difluorochloromethylthio, or trifluoromethylthio,    R 6  represents C 1 -C 6 -alkyl, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, or C 3 -C 6 -cycloalkyl; represents C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkylsulfanyl, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -haloalkylsulfonyl, halo-C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, C 3 -C 6 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine, and/or bromine atoms; or represents —COR 7 , —CONR 8 R 9 , or —CH 2 NR 10 R 11 ,    R 7  represents hydrogen, C 1 -C 6 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, or C 3 -C 6 -cycloalkyl; represents C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, halo-C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, or C 3 -C 6 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine, and/or bromine atoms; or represents 4-(difluoromethyl)-2-methyl-1,3-thiazol-2-yl,    R 8  and R 9  independently of one another represent hydrogen, C 1 -C 6 -alkyl, C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, or C 3 -C 6 -cycloalkyl; or represent C 1 -C 4 -haloalkyl, halo-C 1 -C 3 -alkoxy-C 1 -C 3 -alkyl, C 3 -C 6 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine, and/or bromine atoms, or    R 8  and R 9  together with the nitrogen atom to which they are attached form a saturated heterocycle that is optionally mono- to tetrasubstituted by identical or different substituents selected from the group consisting of halogen and C 1 -C 4 -alkyl and that has 5 to 8 ring atoms, where the heterocycle optionally contains 1 or 2 further non-adjacent heteroatoms selected from the group consisting of oxygen, sulfur, and NR 12 ,    R 10  and R 11  independently of one another represent hydrogen, C 1 -C 6 -alkyl, or C 3 -C 6 -cycloalkyl; or represent C 1 -C 4 -haloalkyl or C 3 -C 6 -halocycloalkyl having in each case 1 to 9 fluorine, chlorine, and/or bromine atoms, or    R 10  and R 11  together with the nitrogen atom to which they are attached form a saturated heterocycle that is optionally mono- or polysubstituted by identical or different substituents selected from the group consisting of halogen and C 1 -C 4 -alkyl and that has 5 to 8 ring atoms, where the heterocycle optionally contains 1 or 2 further non-adjacent heteroatoms selected from the group consisting of oxygen, sulfur, and NR 12 , and    R 12  represents hydrogen or C 1 -C 4 -alkyl.    
   
   
       20 . A thiazolylbiphenylamide of formula (I) as claimed in  claim 18  in which 
 R 1 , R 2 , R 3 , R 4 , and R 5  independently of one another represent hydrogen, fluorine, chlorine, bromine, cyano, methyl, methoxy, methylthio, trifluoromethyl, difluoromethoxy, trifluoromethoxy, difluoromethylthio, or trifluoromethylthio,    R 6  represents methyl, ethyl, n- or isopropyl, n-, iso-, sec-, or tert-butyl, pentyl, or hexyl, methylsulfinyl, ethylsulfinyl, n- or isopropylsulfinyl, n-, iso-, sec-, or tert-butylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or isopropylsulfonyl, n-, iso-, sec-, or tert-butylsulfonyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, trifluoromethyl, trichloromethyl, trifluoroethyl, difluoromethylsulfanyl, difluorochloromethylsulfanyl, trifluoromethylsulfanyl, trifluoromethylsulfinyl, trifluoromethylsulfonyl, trifluoromethoxymethyl, —COR 7 , —CONR 8 R 9 , or —CH 2 NR 10 R 11 ,    R 7  represents hydrogen, methyl, ethyl, n- or isopropyl, tert-butyl, methoxy, ethoxy, tert-butoxy, cyclopropyl; trifluoromethyl, trifluoromethoxy, or 4-(difluoromethyl)-2-methyl-1,3-thiazol-2-yl,    R 8  and R 9  independently of one another represent hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec-, or tert-butyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl; trifluoromethyl, trichloromethyl, trifluoroethyl, or trifluoromethoxymethyl, or    R 8  and R 9  together with the nitrogen atom to which they are attached form a saturated heterocycle selected from the group consisting of morpholine, thiomorpholine, and piperazine, which heterocycle is optionally mono- to tetrasubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, bromine, and methyl, where the piperazine is optionally substituted on the second nitrogen atom by R 12 ,    R 10  and R 1  independently of one another represent hydrogen, methyl, ethyl, n- or isopropyl, n-, iso-, sec-, or tert-butyl, methoxymethyl, methoxyethyl, ethoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl; trifluoromethyl, trichloromethyl, trifluoroethyl, or trifluoromethoxymethyl, or    R 10  and R 11  together with the nitrogen atom to which they are attached form a saturated heterocycle selected from the group consisting of morpholine, thiomorpholine, and piperazine, which heterocycle is optionally mono- to tetrasubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, bromine, and methyl, where the piperazine is optionally substituted on the second nitrogen atom by R 12 , and    R 12  represents hydrogen, methyl, ethyl, n- or isopropyl, or n-, iso-, sec-, or tert-butyl.    
   
   
       21 . A thiazolylbiphenylamide of formula (I) as claimed in  claim 18  in which four of the radicals R 1 , R 2 , R 3 , R 4 , and R 5  represent hydrogen.  
   
   
       22 . A thiazolylbiphenylamide of formula (I) as claimed in  claim 18  in which 
 R 1 , R 2 , R 4 , and R 5  each represent hydrogen, and    R 3  represents hydrogen, halogen, cyano, nitro, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfonyl, or C 3 -C 6 -cycloalkyl; or represents C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkylthio, or C 1 -C 4 -haloalkyl-sulfonyl having in each case 1 to 5 halogen atoms.    
   
   
       23 . A thiazolylbiphenylamide of formula (I) as claimed in  claim 18  in which 
 R 2 , R 4 , and R 5  each represent hydrogen, and    R 1  and R 3  independently of one another represent hydrogen, halogen, cyano, nitro, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfonyl, or C 3 -C 6 -cycloalkyl; or represent C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkylthio, or C 1 -C 4 -haloalkylsulfonyl having in each case 1 to 5 halogen atoms.    
   
   
       24 . A thiazolylbiphenylamide of formula (I) as claimed in  claim 18  in which 
 R 1 , R 4 , and R 5  each represent hydrogen, and    R 2  and R 3  independently of one another represent hydrogen, halogen, cyano, nitro, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfonyl, or C 3 -C 6 -cycloalkyl; or represent C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkylthio, or C 1 -C 4 -haloalkylsulfonyl having in each case 1 to 5 halogen atoms.    
   
   
       25 . A thiazolylbiphenylamide of formula (I) as claimed in  claim 18  in which 
 R 1 , R 3 , and R 5  each represent hydrogen, and    R 2  and R 4  independently of one another represent hydrogen, halogen, cyano, nitro, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfonyl, or C 3 -C 6 -cycloalkyl; or represent C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, C 1 -C 4 -haloalkylthio, or C 1 -C 4 -haloalkylsulfonyl having in each case 1 to 5 halogen atoms.    
   
   
       26 . A thiazolylbiphenylamide of formula (I) as claimed in  claim 18  in which 
 R 6  represents —COR 7 , and    R 7  represents 4-(difluoromethyl)-2-methyl-1,3-thiazol-2-yl.    
   
   
       27 . A thiazolylbiphenylamide of formula (I) as claimed in  claim 18  in which 
 R 6  represents —COR 7 , and    R 7  represents methyl, ethyl, cyclopropyl, or trifluoromethyl.    
   
   
       28 . A thiazolylbiphenylamide of formula (I) as claimed in  claim 18  in which R 6  represents —CHO.  
   
   
       29 . A thiazolylbiphenylamide of formula (I) as claimed in  claim 18  in which R 6  represents methyl, ethyl, n- or isopropyl, n-, iso-, sec-, or tert-butyl, methylsulfinyl, methylsulfonyl, methoxymethyl, ethoxyethyl, cyclopropyl, cyclopentyl, cyclohexyl, trifluoromethyl, trichloromethyl, trifluoromethylsulfanyl, trifluoromethylsulfinyl, trifluoromethylsulfonyl, or trifluoromethoxymethyl.  
   
   
       30 . A process for preparing a thiazolylbiphenylamide of formula (I) as claimed in  claim 18  comprising reacting a thiazolylbiphenylamide of formula (II)  
     
       
         
         
             
             
         
       
       in which R 1 , R 2 , R 3 , R 4 , and R 5  are as defined for formula (I) in  claim 18 , with a halide of formula (III) 
         R 6 —X  (III) 
       in which  
       R 6  is as defined for formula (I) in  claim 18 , and  
       X represents chlorine, bromine, or iodine,  
       in the presence of a base and in the presence of a diluent.  
     
   
   
       31 . A composition for controlling unwanted microorganisms comprising one or more thiazolylbiphenylamides of formula (I) as claimed in  claim 18  and one or more extenders and/or surfactants.  
   
   
       32 . A method of controlling unwanted microorganisms comprising applying an effective amount of one or more thiazolylbiphenylamides of formula (I) according to  claim 18  to the microorganisms and/or their habitat.  
   
   
       33 . A process for preparing compositions for controlling unwanted microorganisms comprising mixing one or more thiazolylbiphenylamide of formula (I) as claimed in  claim 18  with one or more extenders and/or surfactants.