2-(Pyridin-2-yl)-pyrimidines and Their Use for Controlling Harmful Fungi

Abstract

The invention relates to 2-(pyridin-2-yl)-pyrimidine compounds of general formula (I) and their use for controlling pathogenic fungi and as plant protection products that, as an active constituent, contain compounds of this type: In general formula (I), k represents 0, 1, 2, 3; m represents 0, 1, 2, 3, 4 or 5; n represents 1, 2, 3, 4 or 5; R 1 , independent of one another, represents halogen, OH, CN, NO 2 , C 1 -C 4 alkyl, C 1 -C 4 alkyl halide, C 1 -C 4 alkoxy, C 1 -C 4 alkoxy halide, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 3 -C 8 cycloalkyl, C 1 -C 4 alkoxy-C 1 -C 4 alkyl, amino, phenoxy, which is optionally substituted by halogen or C 1 -C 4 alkyl, NHR, NR 2 , C(R a )═N—OR b , S(═O) p A 1 or C(═O)A 2 , or two radicals R 1 bound to adjacent carbon atoms can, together, also represent a group —O-Alk-O—, wherein Alk represents a linear or branched C 1 -C 4 alkylene, and 1, 2, 3 or 4 hydrogen atoms can also be replaced by halogen; R 2 represents C 1 -C 4 alkyl halide, C 1 -C 4 alkoxy, C 1 -C 4 alkoxy halide, hydroxy, halogen, CN or NO 2 ; whereby R 2 can also represent hydrogen or C 1 -C 4 alkyl when at least one of the three following conditions is fulfilled: n represents 3, 4 or 5; k represents 1, 2 or 3; if m is not equal to 0, at least one of the radicals R 1 represents a radical that differs from halogen, C 1 -C 4 alkyl, C 1 -C 4 alkoxy and C 1 -C 4 alkyl halide, and; R 3 represents C 1 -C 4 alkyl.

1 . A 2-(pyridin-2-yl)pyrimidine compound of formula I and agriculturally acceptable salts thereof: 
       
         
           
           
               
               
           
         
         Wherein 
         k is 0, 1, 2 or 3; 
         m is 1, 2, 3, 4 or 5; 
         n is 1, 2, 3, 4 or 5; 
         R 1  is independent of one another and is halogen, OH, CN, NO 2 , C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 8 -cycloalkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, amino, phenoxy, which is optionally substituted by halogen or C 1 -C 4 -alkyl, NHR, NR 2 , C(R a )═N—OR b , S(═O) p A 1  or C(═O)A 2 , provided that at least one of the radicals R 1  is a radical different from halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkyl; and 
         wherein p, R, R a , R b , A 1  and A 2  are defined as follows: 
         R is C 1 -C 4 -alkyl or C 1 -C 4 -alkylcarbonyl, 
         R a  is hydrogen or C 1 -C 4 -alkyl; 
         R b  is C 1 -C 4 -alkyl, C 3 -C 4 -alkenyl or C 3 -C 4 -alkynyl, 
         p is 0, 1 or 2, 
         A 1  is C 1 -C 4 -alkyl, or when p=2 may also be NH 2 , C 1 -C 4 -alkylamino or di-(C 1 -C 4 -alkyl)amino, and 
         A 2  hydrogen, hydroxy, C 1 -C 4 -alkyl, C 1 -C 4 -alkylamino, di-(C 1 -C 4 -alkyl)amino, C 2 -C 4 -alkenyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy; 
         or two radicals R 1  attached to adjacent carbon atoms together may also be a group —O-Alk-O—, wherein Alk is straight-chain or branched C 1 -C 4 -alkylene, wherein 1, 2, 3 or 4 hydrogen atoms may also be replaced with halogen; 
         R 2  is hydrogen or C 1 -C 4 -alkyl 
         R 3  is C 1 -C 4 -alkyl. 
       
     
     
         2 . The compound of formula I according to  claim 1 , wherein n is 3, 4 or 5. 
     
     
         3 . The compound of formula I according to  claim 1 , wherein n is 3. 
     
     
         4 . The compound of formula I according to  claim 1 , wherein m is 1, 2 or 3. 
     
     
         5 . The compound of formula I according to  claim 1 , wherein R 1  is halogen, CN, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 -haloalkoxy provided that at least one of the radicals R 1  is a radical different from halogen, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy and C 1 -C 4 -haloalkyl. 
     
     
         6 . The compound of formula I according to  claim 1 , wherein one of the radicals R 1  is C(R a )═N—OR b . 
     
     
         7 . The compound of formula I according to  claim 1 , wherein the phenyl group substituted by (R 1 ) m    
       
         
           
           
               
               
           
         
         wherein # is the point of attachment to the pyridine ring, is a residue of formula (P) 
       
       
         
           
           
               
               
           
         
         wherein 
         R 11  is hydrogen, fluorine, chlorine, CH 3 , OCH 3 , OCHF 2 , OCF 3  or CF 3 ; 
         R 12  and R 14  independently of one another are each hydrogen, chlorine, fluorine, CH 3 , OCH 3 , OCHF 2 , OCF 3  or CF 3 , wherein one of radicals R 12  and R 14  may also be NO 2 , C(O)CH 3  or COOCH 3 ; 
         R 13  is hydrogen, fluorine, chlorine, cyano, OH, CHO, NO 2 , NH 2 , methylamino, dimethylamino, diethylamino, C 1 -C 4 -alkyl, C 3 -C 8 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloalkoxy, CO(A 2 ), wherein A 2  is C 1 -C 4 -alkyl or C 1 -C 4 -alkoxy, or a group C(R a )═NOR b , wherein R a  is hydrogen or methyl and R b  is C 1 -C 4 -alkyl, propargyl or allyl, or 
         R 12  and R 13  together form a O—CH 2 —O group; and 
         R 15  is hydrogen, fluorine, chlorine or C 1 -C 4 -alkyl, 
         provided that at least one of the radicals R 11 , R 12 , R 13 , R 14  and R 15  is not hydrogen. 
       
     
     
         8 . A composition suitable for controlling harmful fungi, wherein said composition comprises a solid or liquid carrier and
 a compound of formula I according to  claim 1  and/or an agriculturally acceptable salt thereof.   
     
     
         9 . A method for controlling phytopathogenic fungi, wherein said method comprises treating the fungi or the materials, plants, the soil or seed to be protected from fungal attack with an effective amount of a compound of formula I according to  claim 1  and/or an agriculturally acceptable salt thereof.