Compositions and methods for controlling nematodes
Compositions and processes for controlling nematodes are described herein, e.g., nematodes that infest plants or animals. The compounds include oxazoles, oxadiazoles and thiadiazoles.
1. A compound of Formula VIII or a salt thereof,
wherein,
A is an optionally singly or independently multiply substituted aryl, an optionally singly or independently multiply substituted arylalkyl, an optionally singly or independently multiply substituted heteroaryl or an optionally singly or independently multiply substituted heteroarylalkyl wherein the substituents are selected from the group consisting of halo, C 1 -C 6 haloalkyl, C 6 -C 10 aryl, C 4 -C 7 cycloalkyl, C 2 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 6 -C 10 aryl(C 1 -C 6 )alkyl, C 6 -C 10 aryl(C 2 -C 6 ) alkenyl, C 6 -C 10 aryl(C 2 -C 6 ) alkynyl, C 1 -C 6 hydroxyalkyl, amino, ureido, cyano, C 1 -C 6 acylamino, hydroxy, thiol, C 1 -C 6 acyloxy, azido, C 1 -C 6 alkoxy and carboxy, and C(H)O;
C is a heteroaryl selected from the group consisting of furanyl, oxazolyl, or isoxazolyl, each of which can be optionally singly or independently multiply substituted with one or more substituents selected from the group consisting of fluorine, chlorine, CH 3 and OCF 3 ; and
X is O or S.
2. The compound of claim 1 wherein A is an optionally singly or independently multiply substituted heteroaryl.
3. The compound of claim 2 wherein A is selected from the group consisting of pyridyl, pyrazyl, oxazolyl and isoxazolyl, each of which can be optionally singly or independently multiply substituted, wherein the substituents are selected from the group consisting of halo, C 1 -C 6 haloalkyl, C 6 -C 10 aryl, C 4 -C 7 cycloalkyl, C 2 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 6 -C 10 aryl(C 1 -C 6 )alkyl, C 6 -C 10 aryl(C 2 -C 6 ) alkenyl, C 6 -C 10 aryl(C 2 -C 6 )alkynyl, C 1 -C 6 hydroxyalkyl, amino, ureido, cyano, C 1 -C 6 acylamino, hydroxy, thiol, C 1 -C 6 acyloxy, azido, C 1 -C 6 alkoxy and carboxy, and C(H)O.
4. The compound of claim 1 of Formula VIIIa or a salt thereof
wherein,
R 1 and R 5 are independently selected from the group consisting of hydrogen, CH 3 , OCH 3 , F, Cl, Br, CF 3 , and OCF 3 ;
R 2 and R 4 are independently selected from the group consisting of hydrogen, F, Cl, Br, CH 3 , and CF 3 ;
R 3 is selected from the group consisting of hydrogen, CH 3 , CF 3 , F, Cl, Br, OCF 3 , OCH 3 , CN, and C(H)O;
R 7 , R 8 and R 9 are independently selected from the group consisting of hydrogen, F, Cl, CH 3 , and OCF 3 ;
E is O; and
X is O or S.
5. The compound of claim 1 of formula VIIIb or a salt thereof
wherein,
R 1 and R 5 are independently selected from the group consisting of hydrogen, CH 3 , OCH 3 , F, Cl, Br, CF 3 , and OCF 3 ;
R 2 and R 4 are independently selected from the group consisting of hydrogen, F, Cl, Br, CH 3 , and CF 3 ;
R 3 is selected from the group consisting of hydrogen, CH 3 , CF 3 , F, Cl, Br, OCF 3 , OCH 3 , CN, and C(H)O;
R 6 , R 8 and R 9 are independently selected from the group consisting of hydrogen, F, Cl, CH 3 , and OCF 3 ;
E is O; and
X is O or S.
6. A compound of Formula IXa or a salt thereof,
wherein,
R 1 and R 5 are independently selected from the group consisting of hydrogen, CH 3 , OCH 3 , F, Cl, Br, CF 3 , and OCF 3 ;
R 2 and R 4 are independently selected from the group consisting of hydrogen, F, Cl, Br, CH 3 , and CF 3 ;
R 3 is selected from the group consisting of hydrogen, CH 3 , CF 3 , F, Cl, Br, OCF 3 , OCH 3 , CN, and C(H)O;
R 7 , R 8 and R 9 are independently selected from the group consisting of hydrogen, F, Cl, CH 3 , and OCF 3 ;
E is O or S; and
X is CH 2 , O or S.
7. A method for control of unwanted nematodes, the method comprising administering to mammals, birds, or their food, plants, seeds or soil a composition comprising an effective amount of a compound of Formula VIII or a salt thereof,
wherein,
A is an optionally singly or independently multiply substituted aryl, an optionally singly or independently multiply substituted arylalkyl, an optionally singly or independently multiply substituted heteroaryl or an optionally singly or independently multiply substituted heteroarylalkyl wherein the substituents are selected from the group consisting of halo, C 1 -C 6 haloalkyl, C 6 -C 10 aryl, C 4 -C 7 cycloalkyl, C 2 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 6 -C 10 aryl(C 1 -C 6 )alkyl, C 6 -C 10 aryl(C 2 -C 6 ) alkenyl, C 6 -C 10 aryl(C 2 -C 6 ) alkynyl, C 1 -C 6 hydroxyalkyl, amino, ureido, cyano, C 1 -C 6 acylamino, hydroxy, thiol, C 1 -C 6 acyloxy, azido, C 1 -C 6 alkoxy and carboxy, and C(H)O;
C is an optionally singly or independently multiply substituted heteroaryl wherein the substituents are selected from the group consisting of fluorine, chlorine, CH 3 and OCF 3 ; and
X is O or S.
8. The method of claim 7 wherein the composition comprises a surfactant.
9. The method of claim 7 wherein the composition comprises a co-solvent.
10. The method of claim 7 wherein the composition includes one or more of: a fungicide, a herbicide, and a pesticide.
11. A composition comprising the compound of claim 1 in an aqueous carrier.
12. The composition of claim 11 wherein the composition comprises a surfactant.
13. The composition of claim 11 wherein the composition comprises a co-solvent.
14. A method for control of unwanted nematodes, the method comprising administering to mammals, birds, or their food, plants, seeds or soil a composition comprising an effective amount of a compound of claim 6 .
15. The method of claim 14 wherein the composition comprises a surfactant.
16. The method of claim 14 wherein the composition comprises a co-solvent.
17. The method of claim 14 wherein the composition includes one or more of: a fungicide, a herbicide, and a pesticide.
18. A composition comprising the compound of claim 6 in an aqueous carrier.
19. The composition of claim 18 wherein the composition comprises a surfactant.
20. The composition of claim 18 wherein the composition comprises a co-solvent.
21. The compound of claim 1 wherein the compound is 3-(4-chlorophenoxy)-5-(furan-2-yl)-1,2,4-oxadiazole.
22. The method of claim 7 wherein the compound is 3-(4-chlorophenoxy)-5-(furan-2-yl)-1,2,4-oxadiazole.
23. The composition of claim 11 wherein the compound is 3-(4-chlorophenoxy)-5-(furan-2-yl)-1,2,4-oxadiazole.
24. The compound of claim 1 wherein the compound is 3-(3-chlorophenoxy)-5-(furan-2-yl)-1,2,4-oxadiazole.
25. The method of claim 7 wherein the compound is 3-(3-chlorophenoxy)-5-(furan-2-yl)-1,2,4-oxadiazole.
26. The composition of claim 11 wherein the compound is 3-(3-chlorophenoxy)-5-(furan-2-yl)-1,2,4-oxadiazole.
27. The compound of claim 6 wherein the compound is 3-(4-chlorophenyl)-5-(furan-2-ylmethyl)-1,2,4-oxadiazole.
28. The method of claim 14 wherein the compound is 3-(4-chlorophenyl)-5-(furan-2-ylmethyl)-1,2,4-oxadiazole.
29. The composition of claim 18 wherein the compound is 3-(4-chlorophenyl)-5-(furan-2-ylmethyl)-1,2,4-oxadiazole.
30. The compound of claim 6 wherein the compound is 3-(3-chlorophenyl)-5-(furan-2-ylmethyl)-1,2,4-oxadiazole.
31. The method of claim 14 wherein the compound is 3-(3-chlorophenyl)-5-(furan-2-ylmethyl)-1,2,4-oxadiazole.
32. The composition of claim 18 wherein the compound is 3-(3-chlorophenyl)-5-(furan-2-ylmethyl)-1,2,4-oxadiazole.