Crystalline forms of 2-[2-chloro-4-methylsulfony1-3-(2,2,2-trifluoroethoxymethyl)benzoyl]cyclohexan-1,3-dione

• US 8,309,769 B2
• Filed: 03/14/2008
• Issued: 11/13/2012
• Est. Priority Date: 03/15/2007
• Status: Active Grant

• Current Assignee: BASF SE
• Original Assignee: BASF SE
• Inventors: Hupe, Eike, Gewehr, Markus, Erk, Peter, Saxell, Heidi Emilia, Griesser, Ulrich, Tischler, Michaela
• Primary Examiner(s): Gonzalez, Porfirio Nazario
• Assistant Examiner(s): Meadows, James
• Application Number:
  US12/530,666
• Publication Number:
  US 20100041557A1
• Time in Patent Office: 1,705 Days
• Field of Search: None
• US Class Current: 568/31
• CPC Class Codes: A01N 41/10 Sulfones; Sulfoxides
• CPC Class Codes: C07C 317/24 having sulfone or sulfoxide groups and doubly-bound oxygen atoms bound to the same carbon skeleton

Abstract

The present invention relates to two crystalline forms of 2-[2-chloro-4-methylsulfonyl-3-(2,2,2-trifluoro-ethoxymethyl)benzoyl]cyclohexan-1,3-dione, which is also known under the common name tembotrione. The invention also relates to a process for the production of these crystalline forms and formulations for plant protection which contain one of these crystalline forms of tembotrione.

Claims

1. A crystalline form A of 2-[2-chloro-4-methyl-sulfonyl-3-(2,2,2-trifluoroethoxymethyebenzoyl]-cyclohexan-1,3-dione, which in an X-ray powder diffraction diagram at 25°

C. and Cu—

Kα

radiation displays at least 3 of the following reflections, quoted as 2θ

values;

5.6±

0.2°

, 8.9±

0.2°

, 11.1±

0.2°

, 14.0±

0.2°

, 18.9±

0.2°

, 23.4±

0.2°

, 26.7±

0.2°

, 28.9±

0.2° and

36.2±

0.2°

.

2. The crystalline form A of claim 1 with a content of 2-[2-chloro-4-methylsulfonyl-3-(2,2,2-trifluoroethoxymethyl)benzoyl]cyclohexan-1,3-dione of at least 94 wt. %.

3. 2-[2-chloro-4-methylsulfonyl-3-(2,2,2-trifluoro-ethoxymethyl)benzoyl]cyclohexan-1,3-dione consisting of at least 90 wt. % of crystalline form A of claim 1.

4. A process for the production of the crystalline form A of claim 1, comprising:

i) preparing a solution of 2-[2-chloro-4-methylsulfonyl-3-(2,2,2-trifluoro-ethoxymethyl)-benzoyl]cyclohexan-1,3-dione in a polar organic solvent which is selected from the group consisting of cyclic ethers, acetonitrile, methanol, nitromethane, acetic acid, methyl ethyl ketone, pyridine and dimethyl sulfoxide, and

ii) effecting a crystallization of 2-[2-chloro-4-methylsulfonyl-3-(2,2,2-trifluoro-ethoxymethyl)-benzoyl]cyclohexan-1,3-dione

thereby obtaining the crystalline form A of 2-[2-chloro-4-methylsulfonyl-3-(2,2,2-trifluoroethoxymethyl)-benzoyl]cyclohexan-1,3-dione.

9. A plant protection agent containing 2-[2-chloro-4-methylsulfonyl-3-(2,2,2-trifluoroethoxymethyl)-benzoyl]cyclohexan-1,3-dione which consists of at least 90 wt. % of the crystalline form A of claim 1, and one or more additives customary for the formulation of plant protection agents.

10. The plant protection agent of claim 9 in the form of an aqueous suspension concentrate.

11. The plant protection agent of claim 9 in the form of a non-aqueous suspension concentrate.

12. The plant protection agent of claim 9 in the form of a powder or granules dispersible in water.

17. A method for combating undesired plant growth, wherein 2-[2-chloro-4-methylsulfonyl-3-(2,2,2-trifluoroethoxymethyl)-benzoyl]cyclohexan-1,3-dione consisting of at least 90 wt. % of the crystalline form A of claim 1 is used on plants, the habitat thereof and/or on seeds.

5. A crystalline form C of 2-[2-chloro-4-methyl-sulfonyl-3-(2,2,2-trifluoroethoxymethyl)-benzoyl]-cyclohexan-1,3-dione, which in an X-ray powder diffraction diagram at 25°

C. and Cu—

Kα

radiation displays at least 3 of the following reflections, quoted as 2θ

values;

7.4±

0.2°

, 10.8±

0.2°

, 14.8±

0.2°

, 16.6±

0.2°

, 21.1±

0.2°

, 21.6±

0.2° and

33.6±

0.2°

.

6. The crystalline form C of claim 5 with a content of 2-[2-chloro-4-methylsulfonyl-3-(2,2,2-trifluoroethoxymethyl)benzoyl]cyclohexan-1,3-dione of at least 94 wt. %.

7. 2-[2-chloro-4-methylsulfonyl-3-(2,2,2-trifluoro-ethoxymethyl)benzoyl]-cyclohexan-1,3-dione consisting of at least 90 wt. % of crystalline form C of claim 5.

8. A process for the production of the crystalline form C of claim 5 comprising:

i) preparing a hot solution having a temperature of at least 80°

C. of 2-[2-chloro-4-methylsulfonyl-3-(2,2,2-trifluoroethoxymethyl)-benzoyl]cyclohexan-1,3-dione in 2,2-dimethyl-propanol or in an aromatic hydrocarbon or in a mixture of an aromatic hydrocarbon with an aliphatic hydrocarbon, and

ii) effecting a crystallization of 2-[2-chloro-4-methylsulfonyl-3-(2,2,2-trifluoroethoxymethyl)-benzoyl]cyclohexan-1,3-dione by cooling of the solution

thereby obtaining the crystalline form C of 2-[2-chloro-4-methylsulfonyl-3-(2,2,2-trifluoroethoxymethyl)-benzoyl]cyclohexan-1,3-dione.

13. A plant protection agent containing 2-[2-chloro-4-methylsulfonyl-3-(2,2,2-trifluoroethoxymethyl)-benzoyl]cyclohexan-1,3-dione which consists of at least 90 wt. % of the crystalline form C of claim 5 and one or more additives customary for the formulation of plant protection agents.

14. The plant protection agent of claim 13 in the form of an aqueous suspension concentrate.

15. The plant protection agent of claim 13 in the form of a non-aqueous suspension concentrate.

16. The plant protection agent of claim 13 in the form of a powder or granules dispersible in water.

18. A method for combating undesired plant growth, wherein 2-[2-chloro-4-methylsulfonyl-3-(2,2,2-trifluoroethoxymethyl)-benzoyl]cyclohexan-1,3-dione consisting of at least 90 wt. % of the crystalline form C of claim 5 is used on plants, the habitat thereof and/or on seeds.