Novel form of tribenuron-methyl, a process for its preparation and use of the same
a technology of tribenuron and methyl, which is applied in the field of new tribenuronmethyl, can solve the problems of wastewater disposal, and achieve the effects of reducing viscosity, increasing solubility, and ensuring the cleanliness of spray equipmen
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example 1
Preparation of Amorphous Tribenuron-Methyl in Accordance with the Disclosure of EP 0202830
[0064]To a solution of 2-carbomethoxybenzenesul-fonyl isocyanate (22.4 g 93.0 mmol) in dichloromethane (100 mL) was added 2-methoxy-4-methyl-6-methylamino-1,3,5-triazine (10.7 g, 69.6 mmol), followed by a catalytic amount of 1,4-diaza[2.2.2]bicyclooctane. After stirring overnight at ambient temperature under a nitrogen atmosphere, the reaction mixture was concentrated in vacuo. The residue was triturated with diethyl ether and then washed with 1-chlorobutane to yield the title compound as a white powder (28.8 g).
[0065]As shown in FIG. 4, the X-ray powder diffraction pattern of the resulting tribenuron-methyl product has no significant individual signals or peaks, which indicates the tribenuron-methyl product prepared in accordance with the disclosure of EP 0202830 A1 is amorphous.
Preparation of Crystalline Modification I of Tribenuron-Methyl
example 2
Crystallization from Methanol
[0066]Tribenuron-methyl sample prepared in Example 1 (10 g) was taken in a three-necked round bottom flask along with methanol (60 mL) and the resulting slurry was heated to 50° C. to get a homogeneous solution. The insoluble particles, if any, were filtered and the solution was slowly cooled to room temperature. Upon cooling, fine crystals were formed and the heterogeneous mixture was stirred at room temperature for 2 hours. Then, the slurry was filtered and washed with methanol (3 mL). The filtered crystals were dried under vacuum in order to remove the methanol traces from the crystalline product. The crystalline product thus obtained had a purity of >98% and was recovered at not less than 80% yield.
[0067]The obtained crystal was analyzed by IR, X-ray powder diffraction and DSC, and found to be crystalline modification I of tribenuron-methyl as shown in FIGS. 1, 2 and 3, respectively.
[0068]Differential scanning calorimetry (DSC) (FIG. 3) shows an endo...
example 3
Crystallization from Ethanol
[0071]Tribenuron-methyl (5 g) sample prepared in Example 1 was taken in a three-necked round bottom flask along with ethanol (35 mL) and the resulting slurry was heated to 60° C. to get a homogeneous solution. The resultant hot solution was filtered to remove the insoluble (if any) and the solution was slowly cooled to ambient temperature. Product was precipitated out as fine crystal during cooling and the mixture was stirred at room temperature for 2 h. Then, the slurry was filtered, washed with ethanol (3 mL). The filtered crystals were dried under vacuum at room temperature in order to remove the ethanol traces from the crystalline product. The crystalline product thus obtained was having a purity of >98% and the recovered yield was found to be not less than 80%.
[0072]The crystals were characterized as being tribenuron-methyl crystalline modification I using IR spectrometry, X-ray diffraction and DSC, as described in Example 2.
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