Macrocyclic picolinamides as fungicides

Abstract

The disclosure relates to macrocyclic picolinamides of Formula (I) and to the use of these compounds as fungicides.

1 . A compound of Formula I: 
       
         
           
           
               
               
           
         
         wherein: 
         X is C(O)R 5 ; 
         Y is H, C(O)R 5 , or Q; 
         Q is 
       
       
         
           
           
               
               
           
         
         R 1  is H, alkyl, alkenyl, aryl, —C(O)R 4 , each substituted with 0, 1 or multiple R 4 ; 
         R 2  is H, alkyl, alkenyl, aryl —C(O)R 4 , each substituted with 0, 1 or multiple R 4 ; 
         R 3  is H, —C(O)R 6  or —CH 2 OC(O)R 6 ; 
         R 4  is alkyl, alkenyl, halo, haloalkyl, alkoxy, or aryl; 
         R 5  is alkyl, alkoxy, benzyl, benzyloxy, each substituted with 0, 1, or multiple R 7 , wherein 
         each R 7  may be substituted with 0, 1, or multiple R 4 ; 
         R 6  is alkyl or alkoxy, each substituted with 0, 1, or multiple R 4 ; 
         R 7  is alkyl, alkenyl, halo, haloalkyl, alkoxy, aryl, heteroaryl, carbocyclic, heterocyclic, and —Si(R 4 ) 3 , —C(O)R 4 , —S(O) n R 4 , each substituted with 0, 1, or multiple R 4 ; 
         with the proviso that when R 1  and R 2  are H, X and Y are C(O)R 5  and R 5  is tert-butoxy. 
       
     
     
         2 . The compound according to  claim 1  wherein X is C(O)R 5  and Y is chosen from H or C(O)R 5 . 
     
     
         3 . The compound according to  claim 2  wherein X and Y are C(O)R 5  and R 5  is independently chosen from alkyl, alkoxy, benzyl, or benzyloxy, each substituted with 0, 1, or multiple R 7 , wherein each R 7  may be substituted with 0, 1, or multiple R 4 . 
     
     
         4 . The compound according to  claim 3  wherein R 1  and R 2  are independently chosen from H, alkyl, alkenyl, aryl, or —C(O)R 4 , each substituted with 0, 1 or multiple R 4 . 
     
     
         5 . The compound according to  claim 4  wherein R 5  is alkoxy and R 1  and R 2  are H. 
     
     
         6 . The compound according to  claim 5  wherein R 5  is tert-butoxy. 
     
     
         7 . The compound according to  claim 2  wherein Y is hydrogen. 
     
     
         8 . The compound according to  claim 7  wherein R 1  and R 2  are independently chosen from H, alkyl, alkenyl, aryl, or —C(O)R 4 , each substituted with 0, 1 or multiple R 4 . 
     
     
         9 . The compound according to  claim 8  wherein R 1  and R 2  are independently alkyl, alkenyl, aryl, or —C(O)R 4 , each substituted with 0, 1 or multiple R 4 . 
     
     
         10 . The compound according to  claim 9  wherein R 1  and R 2  are independently alkyl, or aryl, each substituted with 0, 1 or multiple R 4 . 
     
     
         11 . The compound according to  claim 8  wherein the amine is protonated to give an ammonium salt of a mineral acid independently chosen from hydrogen chloride, hydrogen bromide, or hydrogen iodide. 
     
     
         12 . The compound according to  claim 11  wherein the ammonium salt is the ammonium hydrochloride. 
     
     
         13 . The compound according to  claim 1  wherein X is C(O)R 5  and Y is Q. 
     
     
         14 . The compound according to  claim 13  wherein R 1  and R 2  are independently chosen from H, alkyl, alkenyl, aryl, or —C(O)R 4 , each substituted with 0, 1, or multiple R 4 . 
     
     
         15 . The compound according to  claim 14  wherein R 1  and R 2  are independently alkyl, alkenyl, aryl, or —C(O)R 4 , each substituted with 0, 1, or multiple R 4 . 
     
     
         16 . A composition for the control of a fungal pathogen including:
 the compound of Formula I; and   a phytologically acceptable carrier material, wherein the combination of Formula I and the carrier is useful for the control of fungal and fungal like pathogens.   
     
     
         17 . The composition according to  claim 16 , wherein the fungal or fungal like pathogen is selected from the group consisting of:  Mycosphaerella graminicola, Septoria tritici, Puccinia triticinaPuccinia striiformis, Venturia inaequalis, Ustilago maydis, Uncinula necator, Rhynchosporium secalis, Magnaporthe grisea, Pseudoperonospora cubensis, Phakopsora pachyrhizi, Phaeosphaeria nodorum, Blumeria graminis tritici, Blumeria graminis hordei, Erysiphe cichoracearum, Glomerella lagenarium, Cercospora beticola, Alternaria solani , and  Pyrenophora teres.    
     
     
         18 . The composition according to  claim 17 , wherein the fungal pathogen or fungal like pathogen is selected from the group consisting of:  Septoria tritici  and  Puccinia tritician ) 
     
     
         19 . A method for the control and prevention plant disease, comprising the steps of:
 applying a fungicidally effective amount of at least one of the compounds of Formula Ito at least one surface selected from the group consisting of: at least one surface of a plant, an area adjacent to a plant, soil in contact with a plant, soil adjacent to a plant, seeds, and equipment for use in agriculture.   
     
     
         20 . The method of  claim 19 , wherein the fungicidally effective amount Formula I is applied to a surface in the range of about 0.01g/m 2  to about 0.45 g/m 2  of Formula I.