Compositions and methods for controlling nematodes
Compositions and methods for controlling nematodes are described herein, e.g., nematodes that infest plants or animals. The compounds include oxazoles, oxadiazoles and thiadiazoles.
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,
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.
32. The method of claim 19 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.
33. The method of claim 19 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.
34. The method of claim 30 wherein E is O.
35. The method of claim 30 wherein E is S.
36. The method of claim 19 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.
37. The method of claim 36 wherein the nematicidal composition comprises 3-phenyl-5-(thiophen-2-yl)-1,2,4-oxadiazole.