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 III or a salt thereof,
wherein,
A is phenyl or pyrazyl, each of which can be optionally independently substituted with one or more substituents selected from the group consisting of halogen, CF 3 , CH 3 , OCF 3 , OCH 3 , CN and C(H)O; and
C is thienyl, furanyl, oxazolyl, or isoxazolyl, each of which can be optionally independently substituted with one or more substituents selected from the group consisting of fluorine, chlorine, CH 3 and OCF 3 .
2 . The treated seed of claim 1 wherein A is phenyl.
3 . The treated seed of claim 1 wherein C is thienyl.
4 . The treated seed of claim 1 wherein C is furanyl.
5 . The treated seed of claim 1 wherein the composition comprises a compound of Formula IIIa 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 the group consisting of from 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.
6 . The treated seed of claim 5 wherein E is S.
7 . The treated seed of claim 5 wherein E is O.
8 . The treated seed of claim 1 wherein the composition comprises a compound of Formula IIIb 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.
9 . The treated seed of claim 8 wherein E is S.
10 . The treated seed of claim 8 wherein E is O.
11 . The treated seed of claim 1 wherein the composition comprises 2-(4-chlorophenyl)-5-(thiophen-2-yl)-1,3,4-oxadiazole.
12 . A compound selected from the group consisting of:
5-(4-fluorophenyl)-2-(furan-2-yl)oxazole;
5-(4-chlorophenyl)-2-(furan-3-yl)oxazole;
2-(4-chlorophenyl)-5-(thiophen-2-yl)-1,3,4-oxadiazole;
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.
13 . A nematicidal composition comprising:
an effective amount of a compound selected from the group consisting of:
5-(4-fluorophenyl)-2-(furan-2-yl)oxazole;
5-(4-chlorophenyl)-2-(furan-3-yl)oxazole;
2-(4-chlorophenyl)-5-(thiophen-2-yl)-1,3,4-oxadiazole;
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; and
one or more of an insecticide, a fungicide, a herbicide, or another pesticide.
14 . The composition of claim 13 wherein the insecticide, fungicide, herbicide or pesticide is selected from the group consisting of an avermectin, milbemycin, imidacloprid, aldicarb, oxamyl, fenamiphos, fosthiazate, metam sodium, etridiazole, penta-chloro-nitrobenzene (PCNB), flutolanil, metalaxyl, mefonoxam, fosetyl-al, silthiofam, fludioxonil, myclobutanil, azoxystrobin, chlorothalonil, propiconazole, tebuconazole, pyraclostrobin, trifloxysulfuron, glyphosate, and halosulfuron.
15 . The composition of claim 13 further comprising water.
16 . The composition of claim 13 further comprising a solvent in which the compound of Formula IV, Formula V, or a salt thereof is dissolved.
17 . The composition of claim 16 further comprising a co-solvent.
18 . The composition of claim 17 wherein the co-solvent is selected from the group consisting of ethyl lactate, methyl soyate, isopropanol, acetone, 1,2-propanediol, n-alkylpyrrolidone, petroleum-based oil and mineral oil.
19 . The composition of claim 13 further comprising an aqueous surfactant.
20 . The composition of claim 13 further comprising a permeation enhancer.