Nematicidal aqueous suspension concentrate compositions

Patent metadata

Field	Value
Publication number	US-9961899-B2
Application number	US-201314649438-A
Country	US
Kind code	B2
Filing date	Dec 4, 2013
Priority date	Dec 4, 2012
Publication date	May 8, 2018
Grant date	May 8, 2018

Abstract

Provided herein are aqueous suspension concentrate compositions comprising biologically active 3,5-disubstituted-1,2,4-oxadiazoles or salts thereof that are useful, for example, in the control of nematodes. Nematodes are active, flexible, elongate organisms that live on moist surfaces or in liquid environments, including films of water within soil and moist tissues within other organisms. Many species of nematodes have evolved to be very successful parasites of plants and animals and, as a result, are responsible for significant economic losses in agriculture and livestock.

First claim

What is claimed is:

1. A method of preparing a nematicidal aqueous suspension concentrate composition comprising an alkylaryl sulfonate dispersant, an organic solvent component comprising a paraffinic hydrocarbon solvent, and a dispersed solid particulate phase comprising a nematicidal component comprising a compound of Formula (I), Formula (II), or a salt thereof,

wherein A is selected from the group consisting of phenyl, pyridyl, pyrazyl, oxazolyl and 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 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 the group consisting of F, Cl, CH 3 , and OCF 3 , the method comprising:
mixing the nematicidal component, the alkylaryl sulfonate dispersant, the organic solvent component, and water to form an aqueous suspension; and
wet milling the aqueous suspension to produce a milled suspension having a reduced particle size, wherein the median size of solid particulates in the dispersed solid particulate phase of the milled suspension is less than about 10 μm.

2. The method of claim 1 wherein the median size of solid particulates in the dispersed solid particulate phase of the milled suspension is less than about 5 μm.

3. The method of claim 1 wherein the median size of solid particulates in the dispersed solid particulate phase of the milled suspension is from about 1 μm to about 5 μm.

4. The method of claim 1 wherein the mean particle size of solid particulates in the dispersed solid particulate phase of the milled suspension is less than about 20 μm.

5. The method of claim 1 wherein the mean particle size of solid particulates in the dispersed solid particulate phase of the milled suspension is from about 0.5 μm to about 10 μm.

6. The method of claim 1 wherein the milled suspension has a polydispersity index of less than about 10.

7. The method of claim 1 wherein the milled suspension has a polydispersity index of from about 1 to about 2.

8. The method of claim 1 wherein the wet milling step comprises ball milling.

9. The method of claim 1 wherein the nematicidal aqueous suspension concentrate composition further comprises a rheology modifying agent.

10. The method of claim 9 wherein the rheology modifying agent comprises a humic substance.

11. The method of claim 1 wherein a secondary dispersant is mixed with the nematicidal component, the dispersant, and water prior to the wet milling step.

12. The method of claim 1 wherein an antifreeze agent is mixed with the nematicidal component, the dispersant, and water prior to the wet milling step.

13. The method of claim 1 wherein a buffer solution is mixed with the nematicidal component, the dispersant, and water prior to the wet milling step.

14. The method of claim 13 wherein the pH of the aqueous suspension during the wet milling step is less than about 10.

15. The method of claim 1 wherein the milled suspension is combined with a stabilizer component.

16. The method of claim 1 wherein the milled suspension is combined with a one or more biological control agents.

17. The method of claim 1 wherein the nematicidal aqueous suspension concentrate composition further comprises an antifoam agent.

18. The method of claim 1 wherein the nematicidal component comprises a compound of Formula (I) or a salt thereof,

wherein A is selected from the group consisting of phenyl, pyridyl, pyrazyl, oxazolyl and 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 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 the group consisting of F, Cl, CH 3 , and OCF 3 .

19. The method of claim 18 wherein the nematicidal component comprises a compound of Formula (Ia) 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 F; R 9 is selected from hydrogen, F, Cl, CH 3 , and OCF 3 ; and E is O or S.

20. The method of claim 1 wherein the nematicidal component comprises a compound of Formula (II), or a salt thereof,

wherein A is selected from the group consisting of phenyl, pyridyl, pyrazyl, oxazolyl and 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 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 the group consisting of F, Cl, CH 3 , and OCF 3 .

Assignees

• Monsanto Technology Llc

Inventors

• Ding Yiwei
• Selness Shaun Raj
• Slomczynska Urszula J

Classifications

• A01N43/653

  1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles · CPC title

• A01N25/04

  Dispersions, {emulsions, suspoemulsions, suspension concentrates} or gels (foams A01N25/16) · CPC title

• A01N37/46

  N-acyl derivatives · CPC title

• A01N43/82 Primary

  five-membered rings with three ring hetero atoms · CPC title

• A01N37/36

  containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids · CPC title