Metalaxyl and prothioconazole cocrystals and methods of making and using

Patent metadata

Field	Value
Publication number	US-9795137-B2
Application number	US-201314391749-A
Country	US
Kind code	B2
Filing date	Mar 12, 2013
Priority date	Apr 25, 2012
Publication date	Oct 24, 2017
Grant date	Oct 24, 2017

Abstract

The invention relates to co-crystals of metalaxyl and prothioconazole, to methods of making them, to compositions containing them and to the methods of using said co-crystals and said compositions to treat crops and plants.

First claim

The invention claimed is:

1. A cocrystal consisting of prothioconazole and metalaxyl, wherein said cocrystal has a water solubility less than the water solubility of metalaxyl alone.

2. The cocrystal of claim 1 , wherein said cocrystal has a melting point of about 100.8° when measured with a Differential Scanning Calorimeter.

3. The cocrystal of claim 1 , wherein the diameter of said cocrystal is about 0.1 μm to about 100 μm.

4. The cocrystal of claim 1 , wherein said cocrystal exhibits the Differential Scanning Calorimeter profile of FIG. 5 when crystallized from butyrolactone.

5. The cocrystal of claim 1 , wherein said cocrystal exhibits the Differential Scanning Calorimeter profile of FIG. 6 when crystallized from acetone.

6. A method of making the cocrystal of claim 1 comprising
(a) dissolving metalaxyl and prothioconazole in a solvent; and
(b) crystallizing the dissolved metalaxyl and prothioconazole,

wherein said cocrystal has a water solubility less than the water solubility of metalaxyl alone.

7. The method of claim 6 , wherein the dissolved metalaxyl and prothioconazole is crystallized in step (b) by the addition of water.

8. The method of claim 6 , wherein the dissolved metalaxyl and prothioconazole is crystallized in step (b) by freezing.

9. The method of claim 6 , wherein the dissolved metalaxyl and prothioconazole is crystallized in step (b) by seeding a solution with preformed metalaxyl and prothioconazole cocrystals.

10. The method of claim 6 , wherein said cocrystal has a melting point at about 100.8° when measured with a Differential Scanning Calorimeter.

11. A method of reducing damage or infestation to a crop caused by weeds, fungi, or pests by applying the cocrystal of claim 1 to said crop or its environment.

12. The method of claim 11 , wherein said cocrystal is applied to a crop from about 0.5 fluid ounces/acre to about 10.0 fluid ounces/acre.

13. The method of claim 11 , wherein said crop is selected from the group consisting of cereals, barley, wheat, winter wheat, triticale winter rye, ground nut, peanuts, rape, bulb onions, oilseed rape, canola, rice, pulses, soybeans, sugar beet, vegetables, and corn.

14. The method of claim 11 , wherein said cocrystal has a melting point of about 100.8° when measured with a Differential Scanning Calorimeter.

15. The method of claim 11 , wherein the diameter of said cocrystal is about 0.1 μm to about 100 μm.

16. A composition consisting essentially of the cocrystal as claimed in claim 1 .

17. The composition of claim 16 , wherein said composition consists essentially of about 0.01% to about 0.5%, about 1% to about 2%, about 2% to about 4%, about 5% to about 10%, or about 20% to about 50% percent by weight of said cocrystal.

18. A method of reducing damage or infestation to a crop caused by weeds, fungi, or pests by applying the composition according to claim 16 to said crop or its environment.

19. The composition of claim 16 , wherein the composition has a water solubility that is reduced by about 90% or more relative to a water solubility of metalaxyl alone.

20. The composition of claim 16 , wherein said composition consists essentially of about 0.1% to about 90% percent by weight of said cocrystal.

Assignees

• Bayer Cropscience Lp

Inventors

• Frizzell David

Classifications

• A01N37/26

  containing the group [IMAGE cpc-sch-A01N-0936.gif]; Thio analogues thereof · CPC title

• A01N43/653 Primary

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

• A01N25/12

  Powders or granules (A01N25/26 takes precedence) · CPC title

• A01N25/00

  Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application {, e.g. seed treatment or sequential application}; Substances for reducing the noxious effect of the active ingredients to organisms other than pests · CPC title

• A01N2300/00

  Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48 · CPC title