Process for preparing a novel crystalline form of mesosulfuron-methyl and use of the same

Patent metadata

Field	Value
Publication number	US-9693558-B2
Application number	US-201514957768-A
Country	US
Kind code	B2
Filing date	Dec 3, 2015
Priority date	Dec 3, 2015
Publication date	Jul 4, 2017
Grant date	Jul 4, 2017

Abstract

A crystalline form of mesosulfuron-methyl of formula (I), the crystal preparation process, the analyses of the crystal through various analytical methods and using the crystal to prepare stable agrochemical formulation. The invention also describes the use of various solvents towards the crystalline form preparation conditions.

First claim

The invention claimed is:

1. A crystalline modification I of mesosulfuron-methyl, exhibiting each of the following reflexes as 2θ values in an X-ray powder diffractogram recorded using Cu-Kα radiation at 25° C.:
2θ=5.41±0.2  (1)

2θ=10.26±0.2  (2)

2θ=10.88±0.2  (3)

2θ=12.14±0.2  (4)

2θ=16.38±0.2  (5)

2θ=18.87±0.2  (6)

2θ=19.47±0.2  (7)

2θ=20.82±0.2  (8)

2θ=21.88±0.2  (9)

2θ=22.55±0.2  (10)

2θ=22.96±0.2  (11)

2θ=23.22±0.2  (12)

2θ=24.10±0.2  (13)

2θ=24.50±0.2  (14)

2θ=26.35±0.2  (15).

2. The crystalline modification I of mesosulfuron-methyl according to claim 1 , exhibiting a Differential Scanning calorimeter (DSC) thermogram having endothermic melting peak with onset at 188.8° C. and peak maximum at about 192.9° C.

3. The crystalline modification I of mesosulfuron-methyl according to claim 1 , exhibiting IR spectrum with the characteristic bands at 3246.88, 2958.83, 1741.75 and 1712.06 cm −1 .

4. A process for the preparation of a crystalline modification I of mesosulfuron-methyl according to claim 1 , comprising:
i) preparing a solution of an amorphous mesosulfuron-methyl in a solvent, wherein the solvent is 1,1-dichloroethane, ethanol, or a mixture thereof;
ii) effecting crystallization of mesosulfuron-methyl from the solution to obtain a precipitate; and
iii) isolating the precipitated crystalline modification I.

5. A composition comprising the crystalline modification I of mesosulfuron-methyl according to claim 1 and at least one herbicidally acceptable auxiliary.

6. The composition according to claim 5 , wherein the composition is formulated as a suspension concentrates (SC), an oil-based suspension concentrates (OD), water-soluble granules (SG), a dispersible concentrate (DC), an emulsifiable concentrates (EC), an emulsion seed dressing, a suspension seed dressing, granules (GR), microgranules (MG), a suspoemulsion (SE) or water-dispersible granules (WG).

7. The composition according to claim 6 , wherein the composition is formulated as an oil-based suspension concentrate (OD).

8. The composition according to claim 6 , wherein the composition is formulated as water-dispersible granules (WG).

9. The composition according to claim 6 , wherein the composition is formulated as water-soluble granules (SG).

10. The composition according to claim 5 , wherein the auxiliary is selected from the group consisting of one or more of a solvent, a diluent, a wetting agent, a dispersant, a thickening agent and an antifoaming agent.

11. The composition according to claim 5 , which comprises crystalline modification I of mesosulfuron-methyl in an amount of less than 75% by weight.

12. A method of controlling undesirable plant growth comprising applying to a plant, plant part, or locus thereof an effective amount of crystalline modification I of mesosulfuron methyl according to claim 1 .

Assignees

• Rotam Agrochem Int Co Ltd

Inventors

• Bristow James Timothy

Classifications

• A01N47/36 Primary

  containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof · CPC title

• A01N25/12

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

• A01N25/14

  wettable · CPC title

• A01N25/04

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

• C07D239/52 Primary

  Two oxygen atoms · CPC title