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 (VI), Formula (VII), or a salt thereof,
wherein A is an optionally substituted aryl or optionally substituted arylalkyl or optionally substituted heteroarylalkyl, wherein said 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 1 -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; and
C is thienyl, furanyl, oxazolyl or isoxazolyl, each of which can be optionally independently substituted with one or more with substituents selected from the group consisting of fluorine, chlorine, CH 3 , and OCF 3 .
2. The compound of claim 1 wherein A is an optionally substituted aryl.
3. The compound of claim 1 wherein A is an optionally substituted arylalkyl.
4. The compound of claim 1 wherein A is an optionally substituted heteroarylalkyl.
5. The compound of claim 1 wherein C is optionally substituted thienyl.
6. The compound of claim 1 wherein C is optionally substituted furanyl.
7. The compound of claim 1 wherein C is optionally substituted oxazolyl.
8. The compound of claim 1 wherein C is optionally substituted isoxazolyl.
9. The compound of claim 1 wherein A is phenyl.
10. The compound of claim 1 wherein the compound is of Formula VIa or a salt thereof,
wherein R 1 and R 5 are independently selected from the group consisting of hydrogen, CH 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, 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 and R 8 are independently selected from the group consisting of hydrogen and fluorine;
R 9 is selected from the group consisting of hydrogen, F, Cl, CH 3 , and OCF 3 ; and
E is O or S.
11. The compound of claim 10 wherein E is O.
12. The compound of claim 10 wherein E is S.
13. The compound of claim 1 wherein the compound is of Formula VIb or a salt thereof,
wherein R 1 and R 5 are independently selected from the group consisting of hydrogen, CH 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, 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 8 is selected from the group consisting of hydrogen and fluorine;
R 6 and R 9 are independently selected from the group consisting of hydrogen, F, Cl, CH 3 , and OCF 3 ; and
E is O or S.
14. The compound of claim 13 wherein E is O.
15. The compound of claim 13 wherein E is S.
16. The compound of claim 1 wherein the compound is of Formula VIIa or a salt thereof,
wherein R 1 and R 5 are independently selected from the group consisting of hydrogen, CH 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, 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 and R 8 are independently selected from the group consisting of hydrogen and fluorine;
R 9 is selected from hydrogen, F, Cl, CH 3 , and OCF 3 ; and
E is O or S.
17. The compound of claim 16 wherein E is O.
18. The compound of claim 16 wherein E is S.
19. The compound of claim 1 wherein the compound is of Formula VIIb or a salt thereof,
wherein R 1 and R 5 are independently selected from the group consisting of hydrogen, CH 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, 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 8 is selected from the group consisting of hydrogen and fluorine;
R 6 and R 9 are independently selected from the group consisting of hydrogen, F, Cl, CH 3 , and OCF 3 ; and
E is O or S.
20. The compound of claim 19 wherein E is O.
21. The compound of claim 19 wherein E is S.
22. A method for control of plant parasitic nematodes, the method comprising administering to a plant, a seed or soil a composition comprising an effective amount of a compound of claim 1 or a salt thereof.
23. The method of claim 22 wherein the composition comprises a surfactant.
24. The method claim 22 wherein the composition includes one or more of an insecticide, a fungicide, a herbicide, or other pesticide.
25. The method of claim 22 wherein the composition comprises a co-solvent.
26. The method of claim 24 wherein the insecticide, fungicide, herbicide or the pesticide is selected from the group consisting of avermectin, ivermectin, milbemycin, imidacloprid, aldicarb, oxamyl, fenamiphos, fosthiazate, metam sodium, etridiazole, penta-chloro-nitrobenzene (PCNB), flutolanil, metalaxyl, mefenoxam, fosetyl-al, silthiofam, fludioxonil, myclobutanil, azoxystrobin, chlorothalonil, propiconazole, tebuconazole, pyraclostrobin, trifloxysulfuron, glyphosate and halosulfuron.
27. The method of claim 22 wherein the plant parasitic nematode is selected from Pratylenchus spp, Heterodera spp, Globodera spp, Meloidogyne spp, Rotylenchulus spp, Hoplolaimus spp, Belonolaimus spp, Longidorus spp, Paratrichodorus spp, Ditylenchus spp, Xiphinema spp, Helicotylenchus spp, Radopholus spp, Hirschmanniella spp, Tylenchorhynchus spp, and Trichodorus spp.
28. The method of claim 22 wherein the composition is applied to seeds.
29. A seed produced in accordance with the method of claim 28 .
30. A seed having a coating comprising a compound of claim 1 or a salt thereof.
31. A seed having a coating comprising a compound selected from the group consisting of:
3-(4 -chloro-2-methylphenyl)-5-(furan-2-yl)-1,2,4-thiadiazole;
3-(2,4-dichlorophenyl)-5-(furan-2-yl)-1,2,4-thiadiazole;
3-(4-bromo-2-methylphenyl)-5-(furan-2-yl)-1,2,4-thiadiazole;
3-(4-bromo-2-chlorophenyl)-5-(furan-2-yl)-1,2,4-thiadiazole;
3-(4-chlorophenyl)-5-(thien-2-yl)-1,2,4-thiadiazole;
3-(4-chlorophenyl)-5-(furan-2-yl)-1,2,4-thiadiazole;
3-(4-chloro-2-fluorophenyl)-5-(furan-2-yl)-1,2,4-thiadiazole; and
5-(2-chloro-4-methylphenyl)-3-(furan-2-yl)-1,2,4-thiadiazole.
32. A method for control of plant parasitic nematodes, the method comprising administering to a plant, a seed or soil a composition comprising an effective amount of a compound of claim 31 or a salt thereof.
33. A seed having a coating comprising a compound of claim 31 or a salt thereof.