MACROCYCLIC PICOLINAMIDES AS FUNGICIDES

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.