Macrocyclic picolinamides as fungicides

Abstract

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

What is claimed is: 
     
         1 . A compound of Formula I 
       
         
           
           
               
               
           
         
         wherein 
         X is hydrogen or C(O)R 3 ; 
         Y is hydrogen, C(O)R 3 , or Q; 
         Q is 
       
       
         
           
           
               
               
           
         
         R 1  is hydrogen, alkyl, alkenyl, aryl, heterocyclyl, alkoxy, or acyl, each optionally substituted with 0, 1 or multiple R 6 ; 
         R 2  is hydrogen, alkyl, alkenyl, aryl, or acyl, each optionally substituted with 0, 1 or multiple R 6 ; 
         R 3  is alkoxy or benzyloxy, each optionally substituted with 0, 1, or multiple R 6 ; 
         R 4  is hydrogen, —C(O)R 5 , or —CH 2 OC(O)R 5 ; 
         R 5  is alkyl, alkoxy, or aryl, each optionally substituted with 0, 1, or multiple R 6 ; 
         R 6  is hydrogen, alkyl, aryl, acyl, halo, alkenyl, alkoxy, heteroaryl, heterocyclyl, or thioalkyl, each optionally substituted with 0, 1, or multiple R 7 ; and 
         R 7  is hydrogen, alkyl, aryl, or halo. 
       
     
     
         2 . The compound according to  claim 1 , wherein X and Y are hydrogen. 
     
     
         3 . The compound according to  claim 2 , wherein R 1  is alkyl or aryl, each optionally substituted with 0, 1 or multiple R 6 . 
     
     
         4 . The compound according to  claim 2 , wherein R 2  is hydrogen or alkyl, each optionally substituted with 0, 1 or multiple R 6 . 
     
     
         5 . The compound according to  claim 1 , wherein X is C(O)R 3  and Y is hydrogen. 
     
     
         6 . The compound according to  claim 5 , wherein R 1  is alkyl or aryl, each optionally substituted with 0, 1 or multiple R 6 . 
     
     
         7 . The compound according to  claim 5 , wherein R 2  is hydrogen or alkyl, each optionally substituted with 0, 1 or multiple R 6 . 
     
     
         8 . The compound according to  claim 1 , wherein X is hydrogen and Y is Q. 
     
     
         9 . The compound according to  claim 8 , wherein R 1  is alkyl or aryl, each optionally substituted with 0, 1 or multiple R 6 . 
     
     
         10 . The compound according to  claim 8 , wherein R 2  is hydrogen or alkyl, each optionally substituted with 0, 1 or multiple R 6 . 
     
     
         11 . The compound according to  claim 9 , wherein R 4  is hydrogen. 
     
     
         12 . The compound according to  claim 9 , wherein R 4  is —C(O)R or —CH 2 OC(O)R 5 . 
     
     
         13 . The compound according to  claim 12 , wherein R 5  is alkyl or alkoxy, each optionally substituted with 0, 1, or multiple R 6 . 
     
     
         14 . The compound according to  claim 13 , wherein R 5  is —CH 3 , —CH(CH 3 ) 2 , —CH 2 OCH 2 CH 3 , or —CH 2 CH 2 OCH 3 . 
     
     
         15 . A composition for the control of a fungal pathogen including at least one of the compounds of Formula I and at least one additional compound selected from the group consisting of: a phytologically acceptable carrier material, a second fungicide, an insecticide, a nematocide, a miticide, an arthropodicide, and a bactericide. 
     
     
         16 . The composition according to  claim 15 , wherein the least one additional compound is at least one phytologically acceptable carrier material. 
     
     
         17 . The composition according to  claim 15  wherein the fungal pathogen is one of Leaf Blotch of Wheat ( Mycosphaerella graminicola ; anamorph:  Zymoseptoria tritici ), Wheat Brown Rust ( Puccinia triticina ), Stripe Rust ( Puccinia striiformis ), Scab of Apple ( Venturia inaequalis ), Blister Smut of Maize ( Ustilago maydis ), Powdery Mildew of Grapevine ( Uncinula necator ), Barley Scald ( Rhynchosporium secalis ), Blast of Rice ( Magnaporthe grisea ), Rust of Soybean ( Phakopsora pachyrhizi ), Glume Blotch of Wheat ( Leptosphaeria nodorum ), Powdery Mildew of Wheat ( Blumeria graminis  f. sp.  tritici ), Powdery Mildew of Barley ( Blumeria graminis  f. sp.  hordei ), Powdery Mildew of Cucurbits ( Erysiphe cichoracearum ), Anthracnose of Cucurbits ( Glomerella lagenarium ), Leaf Spot of Beet ( Cercospora beticola ), Early Blight of Tomato ( Alternaria solani ), and Net Blotch of Barley ( Pyrenophora teres ). 
     
     
         18 . The composition according to  claim 15  wherein the fungal pathogen is one of Leaf Blotch of Wheat ( Zymoseptoria tritici ), Wheat Brown Rust ( Puccinia triticina ), and Rust of Soybean ( Phakopsora pachyrhizi ). 
     
     
         19 . A method for the control and/or the prevention of fungal attack on a plant, the method including the step of:
 applying a fungicidally effective amount of at least one of the compounds of Formula I to at least one portion of a plant, an area adjacent to the plant, soil adapted to support growth of the plant, a root of the plant, and at least a portion of foliage of the plant.   
     
     
         20 . The method according to  claim 19 , wherein the method further includes formulating a composition that includes at least one additional compound selected from the group consisting of a phytologically acceptable carrier material, a second fungicide, an insecticide, a nematocide, a miticide, an arthropodicide, and a bactericide.