Hydrates of 2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1-(2H)-pyrimidinyl]-4-fluoro-N-[[methyl(1-methylethyl)amino]sulfonyl]benzamide

• US 20100035905A1
• Filed: 10/12/2007
• Published: 02/11/2010
• Est. Priority Date: 10/13/2006
• Status: Active Grant

• Current Assignee: BASF SE
• Original Assignee: BASF SE
• Inventors: Wolf, Bernd, Mayer, Guido, Wevers, Jan Hendrik, Seitz, Werner, Schmidt, Thomas, Keil, Michael, Erk, Peter, Zagar, Cyrill, Sievernich, Bernd, Reinhard, Robert, Hamprecht, Gerhard, Cox, Gerhard, Löhr, Sandra, Saxell, Heidi Emilia, Gebhardt, Joachim, Michel, Alfred
• Granted Patent: US 8,357,695 B2
• Time in Patent Office: Days
• US Class Current: 514/274
• CPC Class Codes: A01N 43/54 1,3-Diazines; Hydrogenated 1,3-diazines
• CPC Class Codes: C07D 239/54 as doubly bound oxygen atoms or as unsubstituted hydroxy radicals

Abstract

The present invention relates to hydrates of 2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1-(2H)pyrimidinyl]-4-fluoro-N-[[methyl(1-methylethyl)amino]-sulfonyl]benzamide. The invention also relates to a process for the preparation of these hydrates and to plant protection formulations which comprise hydrates of the phenyluracil I.

Claims

1-17. -17. (canceled)

18. A hydrate of 2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1-(2H)pyrimidinyl]-4-fluoro-N-[[methyl(1-methylethyl)amino]sulfonyl]benzamide.

19. The hydrate according to claim 18, comprising 0.8 to 1.2 mol of water, per mole of 2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1-(2H)pyrimidinyl]-4-fluoro-N-[[methyl(1-methylethyl)amino]sulfonyl]benzamide.

20. The hydrate according to claim 18, with a melting peak in the range of from 100 to 140°

C.

21. The hydrate according to claim 18, with a 2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1-(2H)pyrimidinyl]-4-fluoro-N-[[methyl(1-methylethyl)amino]sulfonyl]benzamide content of at least 94% by weight, based on the total amount of the organic constituents in the hydrate.

28. A process for the preparation of a hydrate according to claim 18, comprising the crystallization of a solution of 2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1-(2H)pyrimidinyl]-4-fluoro-N-[[methyl(1-methyl-ethyl)amino]sulfonyl]benzamide in an organic solvent in the presence of water.

29. A process for the preparation of a hydrate according to claim 18, comprising the suspending of amorphous 2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1-(2H)pyrimidinyl]-4-fluoro-N-[[methyl(1-methyl-ethyl)amino]sulfonyl]benzamide in water or a water-containing organic solvent.

30. A plant protection composition comprising a hydrate according to claim 18 and auxiliaries conventionally employed for the formulation of plant protection compositions.

31. The plant protection composition according to claim 30 in the form of an aqueous suspension concentrate.

32. The plant protection composition according to claim 30 in the form of a nonaqueous suspension concentrate.

33. The plant protection composition according to claim 30 in the form of a water-dispersible powder or water-dispersible granules.

34. A method of controlling undesired vegetation, wherein a hydrate of 2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1-(2H)pyrimidinyl]-4-fluoro-N-[[methyl(1-methylethyl)amino]sulfonyl]benzamide according to claim 18 is allowed to act on plants, their environment and/or on seeds.

22. A hydrate (a) of 2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1-(2H)pyrimidinyl]-4-fluoro-N-[[methyl(1-methylethyl)amino]sulfonyl]benzamide, which in an X-ray powder diffractogram at 25°

C. and Cu-K_α

radiation, shows at least one reflex at the 2θ

value of 11.6±

0.2°

.

23. The hydrate (a) according to claim 22, which additionally shows at least three of the following reflexes, given as 2θ

values;

5.1±

0.2°

, 10.1±

0.2°

, 10.8±

0.2°

, 13.9±

0.2°

, 15.1±

0.2°

, 16.1±

0.2°

, 17.9±

0.2°

, 20.2±

0.2°

, 24.5±

0.2°

.

24. 2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1-(2H)pyrimidinyl]-4-fluoro-N-[[methyl(1-methylethyl)amino]sulfonyl]benzamide, consisting essentially of hydrate (a) according to claim 22.

25. A hydrate (b) of 2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1-(2H)pyrimidinyl]-4-fluoro-N-[[methyl(1-methylethyl)amino]sulfonyl]benzamide, which in an X-ray powder diffractogram at 25°

C. and Cu-K_α

radiation, shows at least one reflex at the 2θ

value of 12.1±

0.2°

.

26. The hydrate (b) according to claim 25, which additionally shows at least three of the following reflexes, given as 2θ

values;

5.2±

0.2°

, 10.2±

0.2°

, 10.9±

0.2°

, 14.0±

0.2°

, 14.6±

0.2°

, 15.3±

0.2°

, 19.2±

0.2°

, 19.9±

0.2°

, 20.5±

0.2°

, 24.7±

0.2°

, 26.7±

0.2°

, 27.8±

0.2°

.

27. 2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1-(2H)-pyrimidinyl]-4-fluoro-N-[[methyl(1-methylethyl)amino]sulfonyl]benzamide, consisting essentially of hydrate (b) according to claim 25.