Formulations of clomazone

• US 9,801,377 B2
• Filed: 06/18/2013
• Issued: 10/31/2017
• Est. Priority Date: 07/27/2012
• Status: Active Grant

• Current Assignee: FMC Corporation
• Original Assignee: FMC Corporation
• Inventors: Liu, Hong, Welch, Michael R., Nicholson, Paul, Cook, Jeffrey A., Ranin, Catherine, Shinn, Sandra L., Pepper, Robert F.
• Primary Examiner(s): Pak, John
• Assistant Examiner(s): BRANSON, DANIEL L
• Application Number:
  US13/920,788
• Publication Number:
  US 20140031231A1
• Time in Patent Office: 1,596 Days
• Field of Search: None
• CPC Class Codes: A01N 25/04 Dispersions, emulsions, suspoemulsions, suspension concentrates or gels foams A01N25/16
• CPC Class Codes: A01N 25/10 Macromolecular compounds
• CPC Class Codes: A01N 25/14 wettable
• CPC Class Codes: A01N 25/28 Microcapsules or nanocapsules
• CPC Class Codes: A01N 33/18 Nitro compounds
• CPC Class Codes: A01N 33/22 having at least one oxygen or sulfur atom and at least one nitro group directly attached to the same aromatic ring system
• CPC Class Codes: A01N 39/02 Aryloxy-carboxylic acids; Derivatives thereof
• CPC Class Codes: A01N 39/04 Aryloxy-acetic acids; Derivatives thereof
• CPC Class Codes: A01N 43/42 condensed with carbocyclic rings
• CPC Class Codes: A01N 43/56 1,2-Diazoles; Hydrogenated 1,2-diazoles
• CPC Class Codes: A01N 43/64 having rings with three nitrogen atoms as the only ring hetero atoms
• CPC Class Codes: A01N 43/653 1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
• CPC Class Codes: A01N 43/80 five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
• CPC Class Codes: A01N 47/30 Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl

Abstract

New formulations of clomazone are provided, as well as new methods for making formulations of clomazone. The new formulations provide improved efficacy, decreased volatility, and/or increased loading of clomazone over the clomazone formulations in the prior art.

Claims

1. A formulation comprising multilayered particles comprising:

a core comprising clomazone,

a first encapsulating layer surrounding the core and comprising polyurea, and

a second encapsulating layer surrounding the first encapsulating layer and comprising polyvinyl alcohol,

wherein the weight ratio of the polyvinyl alcohol to clomazone is from 1;

6 to 1;

4, the weight ratio of polyurea to polyvinyl alcohol is from 1.5;

1 to 1;

1.5, and further wherein the multilayered particles contain at least 50% by weight of ciomazone.

2. An herbicidal composition comprising the formulation of claim 1 and a carrier.

3. The herbicidal composition of claim 2, wherein the herbicidal composition exhibits clomazone volatility control of at least 80%.

4. The formulation of claim 1 comprising linseed oil in the core.

5. The formulation of claim 1 comprising clomazone in the core in an amount of from about 80 wt % to about 97 wt %%.

6. A method for preparing an herbicidal composition comprising the steps of:

a) preparing an aqueous suspension of particles comprising a core and a first encapsulating layer, wherein the core comprises clornazone and the first encapsulating layer comprises polyurea;

b) adding a polyvinyl alcohol to the aqueous suspension; and

c) spray drying the resulting mixture;

wherein the weight ratio of the polyvinyl alcohol to clomazone is from 1;

6 to 1;

4, the weight ratio of polyurea to polyvinyl alcohol is from 1.5;

1 to 1;

1.5, and further wherein the multilayered particles contain at least 50% by weight of clomazone.

7. A method for making water-dispersible granules for delivering agricultural chemicals to a crop comprising the steps of:

forming a water-dispersible powder containing at least one agriculturally active ingredient;

milling the water-dispersible powder; and

forming water-dispersible granules by combining the water-dispersible powder with a clomazone composition, wherein the clomazone composition comprises multilayered clomazone containing particles suspended in an aqueous solution, said multilayered clomazone containing particles comprising;

a core comprising clomazone,

a first encapsulating layer surrounding the core and comprising polyurea, and a second encapsulating layer surrounding the first encapsulating layer and comprising polyvinyl alcohol,

wherein the weight ratio of the polyvinyl alcohol to clomazone is from 1;

6 to 1;

4, the weight ratio of polyurea to polyvinyl alcohol is from 1.5;

1 to 1;

1.5, and further wherein the multilayered particles contain at least 50% by weight of clomazone;

wherein the granules exhibit controlled volatility.

8. The method of claim 7, wherein the step of forming water-dispersible granules comprises:

kneading the clomazone composition into the milled water-dispersible powder to form a wetted powder,

forming granules by subjecting the wetted powder to pan pelletization, and drying the granules.

9. The method of claim 7, wherein the step of forming water-dispersible granules comprises:

kneading the milled water-dispersible powder with water to form a dough,

extruding the dough to form granules,

spray coating the granules with the clomazone composition, and

drying the coated granules.

10. The method of claim 7, wherein the step of forming water-dispersible granules comprises:

kneading the clomazone composition into the milled water-dispersible powder to form a

dough, and extruding the dough to form granules

and drying the granules.

11. The method of claim 7, wherein the step of forming water-dispersible granules comprises:

mixing the milled water dispersible powder with an aqueous encapsulated clomazone composition, and

forming granules from the mixture by fluid bed agglomeration.

12. The method of claim 7, wherein the step of forming water-dispersible granules comprises:

mixing the milled water-dispersible powder with the clomzone composition, and

spray-drying the mixture to form granules.

13. The method of claim 7, wherein the step of forming water-dispersible granules comprises:

mixing the milled water-dispersible powder with the clomzone composition, and

spray-coating the mixture onto an inert carrier material.

14. The method of claim 7, wherein the agriculturally active agent is an herbicide.

15. The method of claim 14, wherein the herbicide is selected from the group consisting of aclonifen, diuron, hexoconazole, quinchlorac, sulfentrazone, hexazinone, 2,4-D, napropamide, and combinations thereof.