4- piridinylmethylsulphonamide derivative as fungicidal plant protection agents

Abstract

Sulfonamides of the formula I where the substituents are as follows: R 1 is hydrogen, alkyl, alkoxy, alkenyl or alkynyl; and R 2 , R 3 , R 4 , R 5 are hydrogen, halogen, alkyl, alkoxy or halomethyl; R 2 and R 3 together may also form a phenyl, cyclopentyl or cyclohexyl ring, it being possible for these rings to carry two groups R 2 ′ and R 3 ′, R 2 ′, R 3 ′ are hydrogen, halogen, alkyl, alkoxy or halomethyl; in case a), if R 2 , R 3 , R 4 and R 5 are hydrogen: X is phenyl substituted by a group C(R 6 )═NOR 7 , where R 6 is alkyl and R 7 is alkyl, benzyl, alkenyl, haloalkyl, haloalkenyl, alkynyl or haloalkynyl; and in case b), if at least one of the groups R 2 , R 3 , R 4 and R 5 is not hydrogen: X is phenyl, naphthyl or a five- or six-membered saturated, or partially unsaturated or aromatic heterocycle which is attached via a carbon atom and contains one to four heteroatoms from the group consisting of O, N and S, where X may be substituted according to the description; Processes for preparing these compounds, compositions comprising them and their use for controlling phytopathogenic harmful fungi.

1 . A method for controlling harmful fungi in the protection of material, comprising:
 treating the materials to be protected from fungal attack with a fungicidally effective amount of a compound of formula I   
       
         
           
           
               
               
           
         
       
       wherein
 R 1  is hydrogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl or benzyl; 
 R 2 , R 3 , R 4  and R 5  are independently of one another hydrogen, halogen, 
 C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy or halomethyl; 
 R 2  and R 3  together may also form a phenyl, cyclopentyl or cyclohexyl ring, it being possible for these rings to carry two groups R 2  and R 3 , 
 R 2  and R 3  independently of one another are hydrogen, halogen, C 1 -C 4 -alkyl, 
 C 1 -C 4 -alkoxy or halomethyl; 
 in case a), if R 2 , R 3 , R 4  and R 5  are hydrogen: 
 X is phenyl substituted by a group —C(R 6 )═NOR 7 , wherein 
 R 6  is C 1 -C 4 -alkyl and 
 R 7  is C 1 -C 8 -alkyl, benzyl, C 2 -C 4 -alkenyl, C 1 -C 4 -haloalkyl, C 2 -C 4 -haloalkenyl, 
 C 2 -C 4 -alkynyl or C 2 -C 4 -haloalkynyl; and 
 in case b), if at least one of the groups R 2 , R 3 , R 4  and R 5  is not hydrogen: 
 X is phenyl, naphthyl or a five- or six-membered saturated, partially unsaturated or aromatic heterocycle which is attached via a carbon atom and contains one to four heteroatoms selected from the group consisting of O, N and S, 
 where X may carry one to four groups R a : 
 R a  is halogen, cyano, nitro, C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, C 1 -C 8 -haloalkoxy, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl, —C(R 6 )═NOR 7 , C 1 -C 4 -alkylaminocarbonyl, 
 di(C 1 -C 4 -alkyl)aminocarbonyl or phenyl or phenoxy, where the rings may carry one to three groups R b : 
 R b  is halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl or C 1 -C 8 -haloalkoxy; 
 R a  or R b  may also be a C 3 -C 4 -alkylene or a C 4 -alkenylene group which, together with two adjacent ring members of the phenyl ring to which it is attached, forms a ring which may be substituted by one or more of the abovementioned groups R a  or R b . 
 
     
     
         2 . The method according to  claim 1 , wherein the treating is performed before the infection of the materials. 
     
     
         3 . The method according to  claim 1 , wherein R 2 , R 3 , R 4  and R 5  of formula I are independently of one another hydrogen, methyl, fluorine, chlorine, CF 3 , OCF 3  or OCHF 2 . 
     
     
         4 . The method according to  claim 1  or  3 , wherein R 1  of formula I is hydrogen, methyl, methoxy, ethoxy, allyl or propargyl. 
     
     
         5 . The method according to  claim 1  or  3 , wherein X of formula I is a phenyl ring which is substituted in the para position. 
     
     
         6 . The method according to  claim 1  or  3 , wherein X of formula I is an aromatic heterocycle. 
     
     
         7 . The method according to  claim 4 , wherein X of formula I is a phenyl ring which is substituted in the para position. 
     
     
         8 . The method according to  claim 4 , wherein X of formula I is an aromatic heterocycle.