Picolinamide compounds with fungicidal activity
View Patent ↗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
R 1 and R 11 are independently chosen from hydrogen or alkyl, optionally substituted with 0, 1 or multiple R 8 ;
alternatively, R 1 and R 11 may be taken together to form a 3-6 membered saturated or partially saturated carbocyclic or heterocyclic ring, optionally substituted with 0, 1 or multiple R 8 ;
R 2 and R 12 are independently chosen from hydrogen, alkyl, aryl, or alkenyl, each optionally substituted with 0, 1 or multiple R 8 ;
R 3 is methyl;
R 4 is chosen from alkyl, aryl, or acyl, each optionally substituted with 0, 1 or multiple R 8 ;
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, or alkoxy, 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 ; and
R 10 is chosen from hydrogen, alkyl, aryl, acyl, halo, alkenyl, alkoxy, or heterocyclyl.
2. A compound according to claim 1 , wherein X and Y are hydrogen.
3. A compound according to claim 2 , wherein R 1 and R 11 are independently chosen from hydrogen or alkyl.
4. A compound according to claim 2 , wherein R 2 and R 12 are independently chosen from hydrogen or alkyl, each optionally substituted with 0, 1 or multiple R 8 .
5. A compound according to claim 2 , wherein R 4 is aryl, optionally substituted with 0, 1 or multiple R 8 .
6. A compound according to claim 2 , wherein R 1 and R 11 are independently chosen from hydrogen or alkyl, R 2 and R 12 are independently hydrogen or alkyl, each optionally substituted with 0, 1 or multiple R 8 , and R 4 is aryl, optionally substituted with 0, 1 or multiple R 8 .
7. A compound according to claim 1 , wherein X is C(O)R 5 and Y is hydrogen.
8. A compound according to claim 7 , wherein R 1 and R 11 are independently chosen from hydrogen or alkyl.
9. A compound according to claim 7 , wherein R 2 and R 12 are independently chosen from hydrogen or alkyl, each optionally substituted with 0, 1 or multiple R 8 .
10. A compound according to claim 7 , wherein R 4 is aryl, optionally substituted with 0, 1 or multiple R 8 .
11. A compound according to claim 7 , wherein R 1 and R 11 are independently chosen from hydrogen or alkyl, R 2 and R 12 are independently hydrogen or alkyl, each optionally substituted with 0, 1 or multiple R 8 , and R 4 is aryl, optionally substituted with 0, 1 or multiple R 8 .
12. A compound according to claim 1 , wherein X is hydrogen and Y is Q.
13. A compound according to claim 12 , wherein R 6 is alkoxy.
14. A compound according to claim 13 , wherein R 7 is hydrogen.
15. A compound according to claim 14 , wherein R 1 and R 11 are independently chosen from hydrogen or alkyl.
16. A compound according to claim 14 , wherein R 2 and R 12 are independently chosen from hydrogen or alkyl, each optionally substituted with 0, 1 or multiple R 8 .
17. A compound according to claim 14 , wherein R 4 is aryl, optionally substituted with 0, 1 or multiple R 8 .
18. A compound according to claim 14 , wherein R 1 and R 11 are independently chosen from hydrogen or alkyl, R 2 and R 12 are independently hydrogen or alkyl, each optionally substituted with 0, 1 or multiple R 8 , and R 4 is aryl, optionally substituted with 0, 1 or multiple R 8 .
19. A compound according to claim 13 , wherein R 7 is chosen from —C(O)R 9 , or —CH 2 OC(O)R 9 .
20. A compound according to claim 19 , wherein R 1 and R 11 are independently chosen from hydrogen or alkyl.
21. A compound according to claim 19 , wherein R 2 and R 12 are independently chosen from hydrogen or alkyl, each optionally substituted with 0, 1 or multiple R 8 .
22. A compound according to claim 19 , wherein R 4 is aryl, optionally substituted with 0, 1 or multiple R 8 .
23. A compound according to claim 19 , wherein R 1 and R 11 are independently chosen from hydrogen or alkyl, R 2 and R 12 are independently hydrogen or alkyl, each optionally substituted with 0, 1 or multiple R 8 , and R 4 is aryl, optionally substituted with 0, 1 or multiple R 8 .
24. A compound according to claim 23 , 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 , or -cyclopropyl.
25. A composition for the control of a fungal pathogen including mixtures of at least one of the compounds of claim 12 and another pesticide including fungicides, insecticides, nematocides, miticides, arthropodicides, bactericides and combinations thereof.
26. A composition for the control of a fungal pathogen including mixtures of at least one of the compounds of claim 14 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 19 and another pesticide including fungicides, insecticides, nematocides, miticides, arthropodicides, bactericides and combinations thereof.