PICOLINAMIDE COMPOUNDS WITH FUNGICIDAL ACTIVITY
This disclosure relates to picolinamides of Formula I and their use as fungicides.
1 . A compound of Formula I
wherein:
X is hydrogen or C(O)R 5 ;
Y is hydrogen, C(O)R 5 , or Q;
Q is
wherein: Z is N or CH;
R 1 is hydrogen or alkyl, substituted with 0, 1 or multiple R 8 ;
R 2 is methyl;
R 3 is chosen from aryl or heteroaryl, each optionally substituted with 0, 1 or multiple R 8 ;
R 4 is chosen from hydrogen, halo, hydroxyl, alkyl or alkoxy;
R 5 is chosen from alkoxy or benzyloxy, each optionally substituted with 0, 1, or multiple R 8 ;
R 6 is chosen from hydrogen, alkoxy, or halo, each optionally substituted with 0, 1, or multiple R 8 ;
R 7 is chosen from hydrogen, —C(O)R 9 , or —CH 2 OC(O)R 9 ;
R 8 is chosen from hydrogen, alkyl, aryl, acyl, halo, alkenyl, alkynyl, alkoxy, cyano or heterocyclyl, each optionally substituted with 0, 1, or multiple R 10 ;
R 9 is chosen from alkyl, alkoxy, or aryl, each optionally substituted with 0, 1, or multiple R 8 ;
R 10 is chosen from hydrogen, alkyl, aryl, acyl, halo, alkenyl, alkoxy, or heterocyclyl.
R 11 is chosen from hydrogen or alkyl, substituted with 0, 1 or multiple R 8 ; and
R 12 is chosen from aryl or heteroaryl, each optionally substituted with 0, 1 or multiple R 8 .
2 . The compound according to claim 1 , wherein X and Y are hydrogen.
3 . The compound according to claim 2 , wherein R 1 and R 11 are independently chosen from hydrogen or alkyl.
4 . The compound according to claim 2 , wherein R 3 and R 12 are independently aryl, each optionally substituted with 0, 1 or multiple R 8 .
5 . The compound according to claim 2 , wherein R 4 is H.
6 . The compound according to claim 2 , wherein R 1 and R 11 are independently chosen from hydrogen or alkyl, R 3 and R 12 are independently aryl, each optionally substituted with 0, 1 or multiple R 8 , and R 4 is H.
7 . The compound according to claim 1 , wherein X is C(O)R 5 and Y is hydrogen.
8 . The compound according to claim 7 , wherein R 1 and R 11 are independently chosen from hydrogen or alkyl.
9 . The compound according to claim 7 , wherein R 3 and R 12 are independently aryl, each optionally substituted with 0, 1 or multiple R 8 .
10 . The compound according to claim 7 , wherein R 4 is H.
11 . The compound according to claim 7 , wherein R 1 and R 11 are independently chosen from hydrogen or alkyl, R 3 and R 12 are independently aryl, each optionally substituted with 0, 1 or multiple R 8 , and R 4 is H.
12 . The compound according to claim 1 , wherein X is hydrogen and Y is Q.
13 . The compound according to claim 12 , wherein Z is N.
14 . The compound according to claim 13 , wherein R 6 is alkoxy.
15 . The compound according to claim 14 , wherein R 7 is hydrogen.
16 . The compound according to claim 15 , wherein R 1 and R 11 are independently chosen from hydrogen or alkyl.
17 . The compound according to claim 15 , wherein R 3 and R 12 are independently aryl, each optionally substituted with 0, 1 or multiple R 8 .
18 . The compound according to claim 15 , wherein R 4 is H.
19 . The compound according to claim 15 , wherein R 1 and R 11 are independently chosen from hydrogen or alkyl, R 3 and R 12 are independently aryl, each optionally substituted with 0, 1 or multiple R 8 , and R 4 is H.
20 . The compound according to claim 14 , wherein R 7 is chosen from —C(O)R 9 , or —CH 2 OC(O)R 9 .
21 . The compound according to claim 20 , wherein R 1 and R il are independently chosen from hydrogen or alkyl.
22 . The compound according to claim 20 , wherein R 3 and R 12 are independently aryl, each optionally substituted with 0, 1 or multiple R 8 .
23 . The compound according to claim 20 , wherein R 4 is H.
24 . The compound according to claim 20 , wherein R 1 and R il are independently chosen from hydrogen or alkyl, R 3 and R 12 are independently aryl, each optionally substituted with 0, 1 or multiple R 8 , and R 4 is H.
25 . The compound according to claim 24 , wherein R 9 is chosen from —CH 3 , —CH 2 OCH 2 CH 3 , —CH 2 CH 2 OCH 3 , —CH(CH 3 ) 2 , —CH 2 CH 2 CH 2 CH 3 , cyclopropyl.
26 . A composition for the control of a fungal pathogen including mixtures of at least one of
1 . pounds of claim 1 and another pesticide including fungicides, insecticides, nematocides, miticides, arthropodicides, bactericides and combinations thereof.
27 . A composition for the control of a fungal pathogen including mixtures of at least one of the compounds of claim 15 and another pesticide including fungicides, insecticides, nematocides, miticides, arthropodicides, bactericides and combinations thereof.
28 . A composition for the control of a fungal pathogen including mixtures of at least one of the compounds of claim 20 and another pesticide including fungicides, insecticides, nematocides, miticides, arthropodicides, bactericides and combinations thereof.
29 . A method for the control and 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 any of claims 1 - 25 to at least one of the plant, an area adjacent to the plant, soil adapted to support growth of the plant, a root of the plant, and foliage of the plant.
30 . A method for the control and prevention of fungal attack on a plant, the method including the step of:
applying a fungicidally effective amount of at least one of the compositions of any of claims 26 - 28 to at least one of the plant, an area adjacent to the plant, soil adapted to support growth of the plant, a root of the plant, and foliage of the plant.