Macrocyclic picolinamides as fungicides

Abstract

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

1 . A compound of Formula I 
       
         
           
           
               
               
           
         
         wherein: 
         X is hydrogen or C(O)R 3 ; 
         Y is hydrogen, C(O)R 3 ; 
         R 1  and R 2  are independently selected from the group consisting of alkyl, alkenyl, and aryl, 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 6  is hydrogen, alkyl, aryl, halo, acyloxy, alkenyl, alkoxy, heteroaryl, heterocyclyl, or thioalkyl, each optionally substituted with 0, 1, or multiple R 7 ; and 
         R 7  is hydrogen, alkyl, haloalkyl, alkoxy, haloalkoxy, aryl, or halo. 
       
     
     
         2 . The compound according to  claim 1 , wherein X and Y are hydrogen. 
     
     
         3 . The compound according to  claim 1 , wherein X is C(O)R 3  and Y is hydrogen. 
     
     
         4 .- 8 . (canceled) 
     
     
         9 . A composition for the control of a fungal pathogen including at least one of the compounds of  claim 1  and at least one additional compound selected from the group consisting of: a phytologically acceptable carrier material, a second fungicide, an insecticide, a nematocides, a miticide, an arthropodicide, a bactericide. 
     
     
         10 . The composition for the control of a fungal pathogen according to  claim 9 , wherein the at least one additional compound is at least one phytologically acceptable carrier material. 
     
     
         11 . The compositions according to  claim 9 , wherein the fungal pathogen is at least one 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 ), 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 ). 
     
     
         12 . The composition according to  claim 11  wherein the fungal pathogen is at least one of the pathogens selected from the group consisting of: Leaf Blotch of Wheat ( Septoria tritici ), Wheat Brown Rust ( Puccinia triticina ), and Rust of Soybean ( Phakopsora pachyrhizi ). 
     
     
         13 . The compositions according to  claim 10  wherein the fungal pathogen is at least one 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 ), 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 ). 
     
     
         14 . The composition according to  claim 13  wherein the fungal pathogen is at least one of the pathogens selected from the group consisting of: Leaf Blotch of Wheat ( Septoria tritici ), Wheat Brown Rust ( Puccinia triticina ), and Rust of Soybean ( Phakopsora pachyrhizi ). 
     
     
         15 . A method for the control and/or 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  claim 1  to at least one portion of a plant, an area adjacent to the plant, a portion of soil adapted to support growth of the plant, a root of the plant, and foliage of the plant.   
     
     
         16 . The method according to  claim 15  wherein the applying step further includes applying at least additional compound selected from the group consisting of: a phytologically acceptable carrier material, a second fungicide, an insecticide, a nematocides, a miticide, an arthropodicide, and a bactericide 
     
     
         17 . The method according to  claim 16 , wherein the additional compound is at least one phytologically acceptable carrier material. 
     
     
         18 . The method according to  claim 16 , wherein the additional compound is at least a one of the following; a second fungicide, an insecticide, a nematocides, a miticide, an arthropodicide, and a bactericide. 
     
     
         19 . (canceled) 
     
     
         20 . (canceled)