Compositions and methods for controlling nematodes

Patent metadata

Field	Value
Publication number	US-9420788-B2
Application number	US-201414567694-A
Country	US
Kind code	B2
Filing date	Dec 11, 2014
Priority date	Aug 13, 2007
Publication date	Aug 23, 2016
Grant date	Aug 23, 2016

Abstract

Compositions and methods for controlling nematodes are described herein, e.g., nematodes that infest plants or animals. The compounds include oxazoles, oxadiazoles and thiadiazoles.

First claim

What is claimed is:

1. A treated seed comprising a nematicidal composition comprising a compound of Formula IV, Formula V, or a salt thereof

wherein A is selected from the group consisting of phenyl, pyrazyl, oxazolyl, and isoxazolyl, each of which can be optionally independently substituted with one or more substituents selected from halogen, CF 3 , CH 3 , OCF 3 , OCH 3 , CN, and C(H)O; and
C is selected from the group consisting of thienyl, furanyl, oxazolyl, and isoxazolyl, each of which can be optionally independently substituted with one or more substituents selected from fluorine, chlorine, CH 3 , and OCF 3 .

2. The seed of claim 1 wherein A is phenyl.

3. The seed of claim 1 wherein A is pyrazyl.

4. The seed of claim 1 wherein A is oxazolyl.

5. The seed of claim 1 wherein A is isoxazolyl.

6. The seed of claim 1 wherein C is thienyl.

7. The seed of claim 1 wherein C is furanyl.

8. The seed of claim 1 wherein C is oxazolyl.

9. The seed of claim 1 wherein C is isoxazolyl.

10. The seed of claim 1 wherein the nematicidal composition comprises a compound of Formula IVa or a salt thereof,

wherein R 1 and R 5 are independently selected from hydrogen, CH 3 , F, Cl, Br, CF 3 and OCF 3 ;
R 2 and R 4 are independently selected from hydrogen, F, Cl, Br, and CF 3 ;
R 3 is selected from hydrogen, CH 3 , CF 3 , F, Cl, Br, OCF 3 , OCH 3 , CN, and C(H)O;
R 7 and R 8 are independently selected from hydrogen and fluorine;
R 9 is selected from hydrogen, F, Cl, CH 3 , and OCF 3 ; and
E is O or S.

11. The seed of claim 1 wherein the nematicidal composition comprises a compound of Formula IVb or a salt thereof,

wherein R 1 and R 5 are independently selected from hydrogen, CH 3 , F, Cl, Br, CF 3 and OCF 3 ;
R 2 and R 4 are independently selected from hydrogen, F, Cl, Br, and CF 3 ;
R 3 is selected from hydrogen, CH 3 , CF 3 , F, Cl, Br, OCF 3 , OCH 3 , CN, and C(H)O;
R 8 is selected from hydrogen and fluorine;
R 6 and R 9 are independently selected from hydrogen, F, Cl, CH 3 , and OCF 3 ; and
E is O or S.

12. The seed of claim 1 wherein the nematicidal composition comprises a compound of Formula Va or a salt thereof,

wherein, R 1 and R 5 are independently selected from hydrogen, CH 3 , F, Cl, Br, CF 3 and OCF 3 ;
R 2 and R 4 are independently selected from hydrogen, F, Cl, Br, and CF 3 ;
R 3 is selected from hydrogen, CH 3 , CF 3 , F, Cl, Br, OCF 3 , OCH 3 , CN, and C(H)O;
R 7 and R 8 are independently selected from hydrogen and fluorine;
R 9 is selected from hydrogen, F, Cl, CH 3 , and OCF 3 ;
and E is O or S.

13. The seed of claim 1 wherein the nematicidal composition comprises a compound of Formula Vb or a salt thereof,

wherein R 1 and R 5 are independently selected from hydrogen, CH 3 , F, Cl, Br, CF 3 and OCF 3 ;
R 2 and R 4 are independently selected from hydrogen, F, Cl, Br, and CF 3 ;
R 3 is selected from hydrogen, CH 3 , CF 3 , F, Cl, Br, OCF 3 , OCH 3 , CN, and C(H)O;
R 8 is selected from hydrogen and fluorine;
R 6 and R 9 are independently selected from hydrogen, F, Cl, CH 3 , and OCF 3 ; and
E is O or S.

14. The seed of claim 10 wherein E is O.

15. The seed of claim 10 wherein E is S.

16. The seed of claim 1 wherein the nematicidal composition comprises a compound selected from the group consisting of:
3-phenyl-5-(thiophen-2-yl)-1,2,4-oxadiazole,
5-(furan-2-yl)-3-phenyl-1,2,4-oxadiazole,
3-(4-fluorophenyl)-5-(thiophen-2-yl)-1,2,4-oxadiazole,
3-(4-fluorophenyl)-5-(furan-2-yl)-1,2,4-oxadiazole,
3-(4-chlorophenyl)-5-(thiophen-2-yl)-1,2,4-oxadiazole,
3-(4-chlorophenyl)-5-(furan-2-yl)-1,2,4-oxadiazole,
3-(4-bromophenyl)-5-(thiophen-2-yl)-1,2,4-oxadiazole,
3-(4-bromophenyl)-5-(furan-2-yl)-1,2,4-oxadiazole,
3-(4-chloro-2-methylphenyl)-5-(furan-2-yl)-1,2,4-oxadiazole,
3-(2,4-dichlorophenyl)-5-(furan-2-yl)-1,2,4-oxadiazole,
3-(4-chlorophenyl)-5-(thiophen-3-yl)-1,2,4-oxadiazole,
3-(4-chlorophenyl)-5-(furan-3-yl)-1,2,4-oxadiazole,
3-(4-fluorophenyl)-5-(thiophen-3-yl)-1,2,4-oxadiazole, and
3-(4-fluorophenyl)-5-(furan-3-yl)-1,2,4-oxadiazole.

17. The seed of claim 16 wherein the nematicidal composition comprises 3-phenyl-5-(thiophen-2-yl)-1,2,4-oxadiazole.

18. The seed of claim 16 wherein the nematicidal composition improves one or more agronomic characteristics of a plant.

19. A method comprising administering to a plant or soil a composition comprising an effective amount of a compound of Formula IV, Formula V, or a salt thereof

wherein
A is selected from the group consisting of phenyl, pyrazyl, oxazolyl, and isoxazolyl, each of which can be optionally independently substituted with one or more substituents selected from halogen, CF 3 , CH 3 , OCF 3 , OCH 3 , CN, and C(H)O; and
C is selected from the group consisting of thienyl, furanyl, oxazolyl, and isoxazolyl, each of which can be optionally independently substituted with one or more substituents selected from fluorine, chlorine, CH 3 , and OCF 3 .

20. The method of claim 19 wherein the compound is administered to improve one or more agronomic characteristics of a plant.

21. The method of claim 20 wherein the compound is administered to improve the vigor of a plant.

22. The method of claim 19 wherein A is phenyl.

23. The method of claim 19 wherein A is pyrazyl.

24. The method of claim 19 wherein A is oxazolyl.

25. The method of claim 19 wherein A is isoxazolyl.

26. The method of claim 19 wherein C is thienyl.

27. The method of claim 19 wherein C is furanyl.

28. The method of claim 19 wherein C is oxazolyl.

29. The method of claim 19 wherein C is isoxazolyl.

30. The method of claim 19 wherein the nematicidal composition comprises a compound of Formula IVa or a salt thereof,

wherein R 1 and R 5 are independently selected from hydrogen, CH 3 , F, Cl, Br, CF 3 and OCF 3 ;
R 2 and R 4 are independently selected from hydrogen, F, Cl, Br, and CF 3 ;
R 3 is selected from hydrogen, CH 3 , CF 3 , F, Cl, Br, OCF 3 , OCH 3 , CN, and C(H)O;
R 7 and R 8 are independently selected from hydrogen and fluorine;
R 9 is selected from hydrogen, F, Cl, CH 3 , and OCF 3 ; and
E is O or S.

31. The method of claim 19 wherein the nematicidal composition comprises a compound of Formula IVb or a salt thereof,

Assignees

• Monsanto Technology Llc

Inventors

• Williams Deryck J
• Dimmic Matt W
• Haakenson William P
• Wideman Al
• Shortt Barry J
• Cheeseright Tim
• Crawford Michael J

Classifications

• A01N43/82 Primary

  five-membered rings with three ring hetero atoms · CPC title

• A61P33/00

  Antiparasitic agents · CPC title

• A61P33/10

  Anthelmintics · CPC title

• A01N43/72 Primary

  having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms · CPC title

• A01N43/76 Primary

  1,3-Oxazoles; Hydrogenated 1,3-oxazoles · CPC title