Compositions and methods for controlling nematodes

Patent metadata

Field	Value
Publication number	US-10827753-B2
Application number	US-201916507535-A
Country	US
Kind code	B2
Filing date	Jul 10, 2019
Priority date	Aug 13, 2007
Publication date	Nov 10, 2020
Grant date	Nov 10, 2020

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 nematicidal composition comprising:
an effective amount of a compound of Formula IV, Formula V, or a salt thereof

wherein,
A is phenyl, pyrazyl, oxazolyl or isoxazolyl, 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 ; and
one or more of an insecticide, a fungicide, a herbicide, or another pesticide 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.

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

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

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

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

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

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

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

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

10. The composition of claim 1 comprising 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 composition of claim 1 comprising 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 composition of claim 1 comprising 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 composition of claim 1 comprising 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 composition of claim 10 wherein E is O.

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

16. The composition of claim 1 comprising 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 composition of claim 16 comprising 3-phenyl-5-(thiophen-2-yl)-1,2,4-oxadiazole.

18. The composition of claim 1 further comprising water.

19. The composition of claim 1 in the form of a concentrate.

20. The composition of claim 1 further comprising a solvent in which the compound of Formula IV, Formula V, or a salt thereof is dissolved.

21. The composition of claim 20 further comprising a co-solvent.

22. The composition of claim 21 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.

23. The composition of claim 1 further comprising an aqueous surfactant.

24. The composition of claim 1 further comprising a permeation enhancer.

25. The composition of claim 16 comprising 5-(furan-2-yl)-3-phenyl-1,2,4-oxadiazole.

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

• A01N43/76 Primary

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

• C07D405/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• A01N47/12

  containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring · CPC title

• C07D413/14

  containing three or more hetero rings · CPC title

• C07D417/04 Primary

  directly linked by a ring-member-to-ring-member bond · CPC title