Form of mefenpyr-diethyl, a process for its preparation and use of the same

Patent metadata

Field	Value
Publication number	US-9809555-B2
Application number	US-201514956991-A
Country	US
Kind code	B2
Filing date	Dec 2, 2015
Priority date	Dec 2, 2015
Publication date	Nov 7, 2017
Grant date	Nov 7, 2017

Abstract

A crystalline form of mefenpyr-diethyl 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 mefenpyr-diethyl, exhibiting each of the following reflexes in an X-ray powder diffractogram recorded using Cu-Kα radiation at 25° C.:
2θ=7.76±0.2  (1)

2θ=10.76±0.2  (2)

2θ=14.00±0.2  (3)

2θ=14.85±0.2  (4)

2θ=16.67±0.2  (5)

2θ=19.49±0.2  (6)

2θ=23.10±0.2  (7)

2θ=23.75±0.2  (8)

2θ=24.48±0.2  (9)

2θ=26.02±0.2  (10)

2θ=26.27±0.2  (11)

2θ=28.49±0.2  (12).

2. The crystalline modification I of mefenpyr-diethyl according to claim 1 , exhibiting IR spectrum with one or more of the characteristic bands at 3086.56, 2983.56, 2903.31, 1731.44 and 1719.50 cm −1 .

3. The crystalline modification I of mefenpyr-diethyl according to claim 1 , exhibiting a Differential Scanning calorimeter (DSC) thermogram exhibits an endothermic melting peak with onset at 48.6° C. and peak maximum at about 50° C. to 54° C.

4. A process for the preparation of a crystalline modification I of mefenpyr-diethyl according to claim 1 , comprising:
i) preparing a solution of an amorphous mefenpyr-diethyl in a solvent, wherein the solvent comprises diethyl ether, acetonitrile, or a combination thereof;
ii) effecting crystallization of mefenpyr-diethyl from the solution to obtain a solid precipitate; and
iii) isolating the precipitated crystalline modification I.

5. A composition comprising a safening amount of the crystalline modification I of mefenpyr-diethyl according to claim 1 , a herbicidally effective amount of at least one sulfonylurea herbicide, and an effective amount of at least one auxiliary.

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

9. The composition according to claim 6 , in the form of a water-dispersible granule (WG).

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, an antifoaming agent and a thickening agent.

11. The composition according to claim 5 , where the weight ratio of the mefenpyr-diethyl to sulfonylurea herbicides is in a range of about 1:10 to about 10:1.

12. The composition according to claim 5 , where the weight ratio of the mefenpyr-diethyl to sulfonylurea herbicides is in a range of about 1:10 to about 5:1.

13. A method of controlling undesirable plant growth, comprising applying to the plant an effective amount of a composition according to claim 5 .

14. The composition according to claim 5 , wherein the sulfonylurea herbicide includes one or more selected from the group consisting of amidosulfuron, azimsulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron-methyl, ethoxysulfuron, flupyrsulfuron-methyl, flazasulfuron, foramsulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron-methyl-sodium, mesosulfuron-methyl, metsulfuron-methyl, nicosulfuron, oxasulfuron, primisulfuron-methyl, prosulfuron, pyrazosulfuron-ethyl, rimsulfuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron-methyl, triasulfuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron-methyl, tritosulfuron and salts thereof, and mixtures thereof.

15. The composition according to claim 14 , wherein the sulfonylurea herbicide includes one or more selected from the group consisting of iodosulfuron-methyl-sodium, mesosulfuron-methyl, bensulfuron-methyl, flupyrsulfuron-methyl, metsulfuron-methyl, nicosulfuron, rimsulfuron, sulfometuron-methyl, thifensulfuron-methyl, tribenuron-methyl, halosulfuron-methyl and salts thereof, and mixtures thereof.

Assignees

• Rotam Agrochem Int Co Ltd

Inventors

• Bristow James Timothy

Classifications

• A01N43/56

  1,2-Diazoles; Hydrogenated 1,2-diazoles · CPC title

• A01N47/36

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

• C07D231/06 Primary

  having one double bond between ring members or between a ring member and a non-ring member · CPC title

• A01N25/12

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

• A01N25/14

  wettable · CPC title