Novel form of rimsulfuron, a process for its preparation and use of the same

Abstract

A crystal form of rimsulfuron is provided that exhibits improved solubility and decreased viscosity. Furthermore, a process for its preparation is provided. The novel crystal form is particularly suitable for use in herbicidal compositions and in the control of unwanted plant growth.

1 . A crystal form A of rimsulfuron, exhibiting at least 3 of the following reflexes in an X-ray powder diffractogram recorded using Cu—Kα radiation at 25° C.:
   2θ=10.868±0.2   (1)
 
   2θ=12.248±0.2   (2)
 
   2θ=12.845±0.2   ( 3 )
 
   2θ=14.249±0.2   (4)
 
   2θ=15.039±0.2   ( 5 )
 
   2θ=16.120±0.2   (6)
 
   2θ=17.434±0.2   ( 7 )
 
   2θ=18.010±0.2   ( 8 )
 
   2θ=19.699±0.2   ( 9 )
 
   2θ=21.801±0.2   (10)
 
   2θ=22.568±0.2   (11)
 
   2θ=26.567±0.2   (12).
 
 
     
     
         2 . The crystal form A of rimsulfuron according to  claim 1 , exhibiting at least 3 of the following reflexes in an X-ray powder diffractogram recorded using Cu—Kα radiation at 25° C.:
   2θ=10.868±0.2   (1)
 
   2θ=12.248±0.2   (2)
 
   2θ=12.845±0.2   ( 3 )
 
   2θ=16.120±0.2   (6)
 
   2θ=21.801±0.2   (10)
 
   2θ=26.567±0.2   (12).
 
 
     
     
         3 . The crystal form A of rimsulfruon according  claim 1  exhibiting at least four of the said reflexes. 
     
     
         4 . The crystal form A of rimsulfuron according to  claim 1  exhibiting at least five of the said reflexes. 
     
     
         5 . The crystal form A of rimsulfuron according to  claim 1 , exhibiting IR spectrum with the characteristic bands at 3257.17 cm −1  and 2943.91 cm −1 . 
     
     
         6 . A process for the preparation of a crystal form A of rimsulfuron according to  claim 1 , the process comprising:
 i) preparing a solution of an amorphous rimsulfuron in a solvent;   ii) effecting crystallization of rimsulfuron from the solution to obtain a solid precipitate; and   iii) isolating the solid precipitate.   
     
     
         7 . The process according to  claim 6 , wherein the solvent comprises an alcohol. 
     
     
         8 . The process according to  claim 6 , wherein the solvent is methanol and/or ethanol 
     
     
         9 . A composition comprising the crystal form A of rimsulfuron according to  claim 1  and at least one auxiliary. 
     
     
         10 . The composition according to  claim 9 , in the form of a suspension concentrate (SC), an oil-based suspension concentrate (OD), water-soluble granules (SG), a dispersible concentrate (DC), an emulsifiable concentrate (EC), an emulsion seed dressing, a suspension seed dressing, granules (GR), microgranules (MG), a suspoemulsion (SE) or water-dispersible granules (WG). 
     
     
         11 . The composition according to  claim 9 , wherein the auxiliary is selected from one or more of a solvent, a diluent, a wetting agent, a dispersant, and a thickener. 
     
     
         12 . The composition according to  claim 9 , which comprises crystal form A of rimsulfuron in an amount of less than 75% by weight. 
     
     
         13 . A method for controlling unwanted plant growth, comprising applying to the plant, plant part, or surroundings of the plant, a herbicidal effective amount of a crystal form A of rimsulfuron according to  claim 1 . 
     
     
         15 . A process for preparing crystal form A of rimusulfuron according to  claim 1 . 
     
     
         16 . A composition comprising crystal form A of rimusulfuron according to  claim 1 .