Macrocyclic picolinamides as fungicides

Abstract

The disclosure relates to macrocyclic picolinamides of Formula I and their use as fungicides.

What is claimed: 
     
         1 . A compound of Formula I: 
       
         
           
           
               
               
           
         
         wherein, R 1  is H, —C(O)R 3 , or —CH 2 OC(O)R 3 ; 
         R 2  is H, halogen, alkyl, alkenyl, alkynyl, aryl, heterocyclyl, alkylthio, arylthio or heteroarylthio each substituted with 0, 1 or multiple R 5 , —CH 2 R 4 , —CH 2 OC(O)R 4 , —C(O)OR 4 , —CH 2 OS(O) 2 R 4 , or —CH 2 OR 4 ; 
         R 3  is alkyl or alkoxy, substituted with 0, 1, or multiple R 5 ; 
         R 4  is H, alkyl, alkenyl, aryl, arylalkyl, or heterocyclyl, each substituted with 0, 1 or multiple R 5 ; 
         R 5  is alkyl, alkenyl, halo, haloalkyl, alkoxy, haloalkoxy, arylalkoxy, cyano, aryl or heterocyclyl, each substituted with 0, 1 or multiple R 6 ; and 
         R 6  is alkyl, alkenyl, halo, haloalkyl, alkoxy, haloalkoxy, arylalkoxy, cyano, aryl or heterocyclyl. 
       
     
     
         2 . The compound according to  claim 1 , wherein:
 R 1  is H, —C(O)R 3 , or —CH 2 OC(O)R 3 ;   R 2  is alkyl, alkenyl, or aryl, each substituted with 0, 1 or multiple R 5 ;   R 3  is alkyl or alkoxy, substituted with 0, 1, or multiple R 5 ;   R 5  is alkyl, alkenyl, halo, haloalkyl, alkoxy, haloalkoxy, arylalkoxy, cyano, aryl or heterocyclyl, each substituted with 0, 1 or multiple R 6 ; and   R 6  is alkyl, alkenyl, halo, haloalkyl, alkoxy, haloalkoxy, arylalkoxy, cyano, aryl or heterocyclyl.   
     
     
         3 . A compound according to  claim 3 , wherein:
 R 1  is H, —C(O)R 3 , or —CH 2 OC(O)R 3 ;   R 2  is alkyl, alkenyl, or aryl, each substituted with 0, 1 or multiple R 5 ;   R 3  is alkyl or alkoxy, substituted with 0, 1, or multiple R 5 ; and   R 5  is alkyl, halo, haloalkyl, or aryl.   
     
     
         4 . A compound according to  claim 3 , wherein:
 R 1  is H, —C(O)R 3 , or —CH 2 OC(O)R 3 ;   R 2  is alkyl, alkenyl, or aryl, each substituted with 0, 1 or multiple R 5 ;   R 3  is alkyl; and   R 5  is alkyl, halo, haloalkyl, or aryl.   
     
     
         5 . A composition for the control of a fungal pathogen, including the compound of Formula I 
       
         
           
           
               
               
           
         
         wherein, R 1  is H, —C(O)R 3 , or —CH 2 OC(O)R 3 ; 
         R 2  is H, halogen, alkyl, alkenyl, alkynyl, aryl, heterocyclyl, alkylthio, arylthio or heteroarylthio each substituted with 0, 1 or multiple R 5 , —CH 2 R 4 , —CH 2 OC(O)R 4 , —C(O)OR 4 , —CH 2 OS(O) 2 R 4 , or —CH 2 OR 4 ; 
         R 3  is alkyl or alkoxy, substituted with 0, 1, or multiple R 5 ; 
         R 4  is H, alkyl, alkenyl, aryl, arylalkyl, or heterocyclyl, each substituted with 0, 1 or multiple R 5 ; 
         R 5  is alkyl, alkenyl, halo, haloalkyl, alkoxy, haloalkoxy, arylalkoxy, cyano, aryl or heterocyclyl, each substituted with 0, 1 or multiple R 6 ; and 
         R 6  is alkyl, alkenyl, halo, haloalkyl, alkoxy, haloalkoxy, arylalkoxy, cyano, aryl or heterocyclyl, and 
         at least one phytologically acceptable carrier and/or at least one agriculturally active ingredient selected from the group consisting of pesticides, fungicides, insecticides, nematocides, miticides, arthropodicides, bactericides and combinations thereof. 
       
     
     
         6 . A method for treating a plant, comprising the steps of:
 applying an amount of at least one of the compounds of Formula I   
       
         
           
           
               
               
           
         
       
       wherein, R 1  is H, —C(O)R 3 , or —CH 2 OC(O)R 3 ;
 R 2  is H, halogen, alkyl, alkenyl, alkynyl, aryl, heterocyclyl, alkylthio, arylthio or heteroarylthio each substituted with 0, 1 or multiple R 5 , —CH 2 R 4 , —CH 2 OC(O)R 4 , —C(O)OR 4 , —CH 2 OS(O) 2 R 4 , or —CH 2 OR 4 ; 
 R 3  is alkyl or alkoxy, substituted with 0, 1, or multiple R 5 ; 
 R 4  is H, alkyl, alkenyl, aryl, arylalkyl, or heterocyclyl, each substituted with 0, 1 or multiple R 5 ; 
 R 5  is alkyl, alkenyl, halo, haloalkyl, alkoxy, haloalkoxy, arylalkoxy, cyano, aryl or heterocyclyl, each substituted with 0, 1 or multiple R 6 ; and 
 R 6  is alkyl, alkenyl, halo, haloalkyl, alkoxy, haloalkoxy, arylalkoxy, cyano, aryl or heterocyclyl, to at least one portion of a plant, an area adjacent to a plant, and/or soil adapted to support growth of a plant, wherein said amount is effective for the control of at least one plant pathogen. 
 
     
     
         7 . The compositions according to  claim 6 , wherein the effective amount of the compound is effective against at least one plant pathogen selected from the group consisting of: Leaf Blotch of Wheat ( Mycosphaerella graminicola ; anamorph:  Septoria tritici ), Wheat Brown Rust ( Puccinia triticina ), Stripe Rust ( Puccinia striiformis ), and Black Sigatoka ( Mycosphaerella fujiensis ). 
     
     
         8 . The composition according to  claim 7 , wherein the plant pathogen is at least one organism selected from the group consisting of ( Septoria tritici ) and ( Puccinia triticina ).