Acetyl CoA carboxylase modulators

Patent metadata

Field	Value
Publication number	US-10207995-B2
Application number	US-201414896616-A
Country	US
Kind code	B2
Filing date	Jun 13, 2014
Priority date	Jun 13, 2013
Publication date	Feb 19, 2019
Grant date	Feb 19, 2019

Abstract

Provided herein are compounds that exhibit activity as acetyl-CoA carboxylase modulators (e.g., inhibitors) and are useful, for example, in methods for the control of fungal pathogens in plants.

First claim

What is claimed is:

1. A method of controlling fungal pathogens, the method comprising administering to a plant, a seed or soil a composition comprising an effective amount of a compound of Formula I or a salt thereof,

wherein
R 1 is selected from the group consisting of hydrogen, halogen, alkyl, alkoxy, haloalkyl, and haloalkoxy;
R 2 is selected from the group consisting of aryl and heteroaryl, each of which may be optionally independently substituted with one or more substituents selected from the group consisting of halogen, OH, CN, alkyl, alkoxy, haloalkyl, haloalkoxy, alkenyl, C 1 to C 4 hydroxyalkyl, N(R 7 R 8 ), and NR 9 C(O)R 10 , wherein R 9 is selected from the group consisting of hydrogen and alkyl and R 10 is alkyl;
R 3 , R 4 , R 5 , and R 6 are each independently selected from the group consisting of hydrogen, halogen, OH, alkyl, alkoxy, haloalkyl, haloalkoxy, C 1 to C 4 hydroxyalkyl, N(R 7 R 8 ), NR 9 C(O)R 10 , and C(O)R 11 , wherein R 9 is selected from the group consisting of hydrogen and alkyl and R 10 and R 11 are alkyl;
X is selected from the group consisting of a bond, CH 2 , O, S, NH, and N(CH 3 );
Y is selected from the group consisting of OH, NH 2 , N(H)OH, N(CH 3 )OH, and N(R 7 R 8 ); and
Z is selected from the group consisting of aryl and heteroaryl, each of which may be optionally independently substituted with one or more substituents selected from the group consisting of halogen, alkyl, alkoxy, haloalkyl, haloalkoxy, C 1 to C 4 hydroxyalkyl, CN, and C(H)O;
wherein when R 2 is substituted with N(R 7 R 8 ) or when any one of R 3 , R 4 , R 5 , and R 6 is N(R 7 R 8 ), R 7 and R 9 are each independently selected from the group consisting of hydrogen and alkyl; and
when Y is N(R 7 R 8 ), R 7 and R 9 are each independently selected from the group consisting of hydrogen, alkyl, and hydroxyalkyl.

2. The method of claim 1 wherein the compound is of Formula Ia or a salt thereof,

wherein
R 1 is selected from the group consisting of hydrogen, halogen, alkyl, alkoxy, haloalkyl, and haloalkoxy;
R 3 , R 4 , R 5 , and R 6 are each independently selected from the group consisting of hydrogen, halogen, OH, alkyl, alkoxy, haloalkyl, haloalkoxy, C 1 to C 4 hydroxyalkyl, N(R 7 R 8 ), NR 9 C(O)R 10 , and C(O)R 11 , wherein R 9 is selected from the group consisting of hydrogen and alkyl and R 10 and R 11 are alkyl;
X is selected from the group consisting of CH 2 , O, S, NH, and N(CH 3 ); and
Y is selected from the group consisting of OH, NH 2 , N(H)OH, N(CH 3 )OH, and N(R 7 R 8 );
wherein when any one of R 3 , R 4 , R 5 , and R 6 is N(R 7 R 8 ), R 7 and R 8 are each independently selected from the group consisting of hydrogen and alkyl; and
when Y is N(R 7 R 8 ), R 7 and R 8 are each independently selected from the group consisting of hydrogen, alkyl, and hydroxyalkyl.

3. The method of claim 1 wherein the compound is of Formula Ib or a salt thereof,

wherein
R 1 is selected from the group consisting of hydrogen, halogen, alkyl, alkoxy, haloalkyl, and haloalkoxy;
R 3 , R 4 , R 5 , and R 6 are each independently selected from the group consisting of hydrogen, halogen, OH, alkyl, alkoxy, haloalkyl, haloalkoxy, C 1 to C 4 hydroxyalkyl, N(R 7 R 8 ), NR 9 C(O)R 10 , and C(O)R 11 , wherein R 9 is selected from the group consisting of hydrogen and alkyl and R 10 and R 11 are alkyl;
Y is selected from the group consisting of OH, NH 2 , N(H)OH, N(CH 3 )OH, and N(R 7 R 8 ); and
E is selected from the group consisting of S, O, and N(CH 3 );
wherein when any one of R 3 , R 4 , R 5 , and R 6 is N(R 7 R 8 ), R 7 and R 8 are each independently selected from the group consisting of hydrogen and alkyl; and
when Y is N(R 7 R 8 ), R 7 and R 8 are each independently selected from the group consisting of hydrogen, alkyl, and hydroxyalkyl.

4. The method of claim 1 wherein R 2 is phenyl.

5. The method of claim 1 wherein Z is phenyl.

6. The method of claim 1 wherein R 1 is hydrogen.

7. The method of claim 1 wherein R 1 is halogen.

8. The method of claim 1 wherein R 3 , R 4 , R 5 , and R 6 are each hydrogen.

9. The method of claim 1 wherein X is a bond.

10. The method of claim 1 wherein Y is NH 2 .

11. The method of claim 1 wherein R 1 is selected from the group consisting of hydrogen, halogen, CH 3 , OCH 3 , CF 3 , and OCF 3 .

12. The method of claim 1 wherein R 3 , R 4 , R 5 , and R 6 are each independently selected from the group consisting of hydrogen, halogen, OH, CH 3 , OCH 3 , CF 3 , and OCF 3 .

13. The method of claim 1 wherein X is O.

14. The method of claim 1 wherein Y is OH.

15. The method of claim 1 wherein Z is thienyl.

16. The method of claim 1 wherein the method comprises administering the composition to a seed.

17. A treated seed prepared according to the method of claim 16 .

18. The method of claim 1 wherein the method comprises exogenously administering the composition to a plant.

19. The method of claim 18 wherein the composition is applied to the foliage of a plant.

20. The method of claim 18 wherein the method comprises applying the composition to the soil surrounding the root zone of a plant.

21. A method of modulating acetyl-CoA carboxylase (ACCase) in a biological organism, the method comprising administering to the biological organism a composition comprising an effective amount of a compound of Formula I or a salt thereof,

wherein
R 1 is selected from the group consisting of hydrogen, halogen, alkyl, alkoxy, haloalkyl, and haloalkoxy;
R 2 is selected from the group consisting of aryl and heteroaryl, each of which may be optionally independently substituted with one or more substituents selected from the group consisting of halogen, OH, CN, alkyl, alkoxy, haloalkyl, haloalkoxy, alkenyl, C 1 to C 4 hydroxyalkyl, N(R 7 R 8 ), and NR 9 C(O)R 10 , wherein R 9 is selected from the group consisting of hydrogen and alkyl and R 10 is alkyl;
R 3 , R 4 , R 5 , and R 6 are each independently selected from the group consisting of hydrogen, halogen, OH, alkyl, alkoxy, haloalkyl, haloalkoxy, C 1 to C 4 hydroxyalkyl, N(R 7 R 8 ), NR 9 C(O)R 10 , and C(O)R 11 , wherein R 9 is selected from the group consisting of hydrogen and alkyl and R 10 and R 11 are alkyl;
X is selected from the group consisting of a bond, CH 2 , O, S, NH, and N(CH 3 );
Y is selected from the group consisting of OH, NH 2 , N(H)OH, N(CH 3 )OH, and N(R 7 R 8 ); and
Z is selected from the group consisting of aryl and heteroaryl, each of which may be optionally independently substituted with one or more substituents selected from the group consisting of halogen, alkyl, alkoxy, haloalkyl, haloalkoxy, C 1 to C 4 hydroxyalkyl, CN, and C(H)O;
wherein when R 2 is substituted with N(R 7 R 8 ) or when any one of R 3 , R 4 , R 5 , and R 6 is N(R 7 R 8 ), R 7 and R 8 are each independently selected from the group consisting of hydrogen and alkyl; and
when Y is N(R 7 R 8 ), R 7 and R 8 are each independently selected from the group consisting of hydrogen, alkyl, and hydroxyalkyl.

Assignees

• Monsanto Technology Llc

Inventors

• Slomczynska Urszula
• Dimmic Matthew W
• Haakenson Jr William P
• Bennett Jennifer L
• Shortt Barry J
• Taylor Christina M
• Williams Deryck Jeremy

Classifications

• A01N57/20

  containing acyclic or cycloaliphatic radicals · CPC title

• A01N57/24

  containing heterocyclic radicals · CPC title

• A01N43/84

  six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4 · CPC title

• A61K31/045

  Hydroxy compounds, e.g. alcohols; Salts thereof, e.g. alcoholates · CPC title

• C07D215/14 Primary

  Radicals substituted by oxygen atoms · CPC title