Picolinamide compounds with fungicidal activity

Patent metadata

Field	Value
Publication number	US-10588318-B2
Application number	US-201815953394-A
Country	US
Kind code	B2
Filing date	Apr 13, 2018
Priority date	Dec 30, 2014
Publication date	Mar 17, 2020
Grant date	Mar 17, 2020

Abstract

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

First claim

What is claimed is:

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 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 substituted with 0, 1, or multiple R 8 ;
R 6 is chosen from hydrogen, alkoxy, or halo, each 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 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 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 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 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 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 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 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 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 11 are independently chosen from hydrogen or alkyl.

22. The compound according to claim 20 , wherein R 3 and R 12 are independently aryl, each 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 11 are independently chosen from hydrogen or alkyl, R 3 and R 12 are independently aryl, each 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 , or -cyclopropyl.

26. A composition for the control of a fungal pathogen including mixtures of at least one of the compounds of claim 1 and another pesticide selected from the group consisting of 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 selected from the group consisting of 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 selected from the group consisting of fungicides, insecticides, nematocides, miticides, arthropodicides, bactericides and combinations thereof.

29. A method for the control 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 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 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 claim 26 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.

Assignees

• Dow Agrosciences Llc

Inventors

• Bravo-Altamirano Karla
• Lu Yu
• Loy Brian A
• Buchan Zachary A
• Jones David M
• Wilmot Jeremy
• Rigoli Jared W
• Dekorver Kyle A
• Daeuble Sr John F
• Herrick Jessica
• Wang Xuelin
• Yao Chenglin
• Meyer Kevin G

Classifications

• A01N43/40 Primary

  six-membered rings · CPC title

• C07D405/12

  linked by a chain containing hetero atoms as chain links · CPC title

• C07D409/14

  containing three or more hetero rings · CPC title

• C07C229/22

  the carbon skeleton being further substituted by oxygen atoms · CPC title

• C07C229/20

  the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups · CPC title