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Novel form of sulfentrazone, process for its preparation and use thereof

A technology of sulfentrazone and methanesulfonamide, applied in the direction of botany equipment and methods, applications, herbicides and algicides, etc.

Active Publication Date: 2018-12-21
JIANGSU ROTAM CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] To address some or all of the problems with the existing amorphous form of sulfentrazone, new stable crystalline forms of sulfentrazone have been prepared

Method used

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  • Novel form of sulfentrazone, process for its preparation and use thereof
  • Novel form of sulfentrazone, process for its preparation and use thereof
  • Novel form of sulfentrazone, process for its preparation and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0109] Example 1: Preparation of amorphous sulfentrazone according to the disclosure of US Patent No. 4,818,275 (Example 13, Example 14 and Example 15):

[0110] 1. 1-(5-Amino-2,4-dichlorophenyl)-3-methyl-4-difluoromethyl-Δ as an intermediate 2 -1, 2, 4 - three Preparation of oxazolin-5-one (embodiment 13)

[0111] Step A - Synthesis of pyruvate, 2,4-dichlorophenylhydrazone as intermediate

[0112] To a stirred solution of 16.2 g (0.07 mol) of commercially available 2,4-dichlorophenylhydrazine hydrochloride in 100 ml of ethanol was added 9.2 g (0.11 mol) of pyruvic acid in 100 ml of water in one portion. The reaction mixture was stirred for 10 minutes and the resulting solid was collected by filtration to give 13.5 g of pyruvic acid, 2,4-dichlorophenylhydrazone, m.p. 193°C-194°C when dry. This reaction was repeated several times.

[0113]

[0114] Step B - 1-(2,4-dichlorophenyl)-3-methyl-Δ as intermediate 2 -Synthesis of 1,2,4-triazolin-5-one

[0115] To a stir...

Embodiment 2

[0133] Example 2 - Crystallization from xylene

[0134] A sample of amorphous sulfentrazone (10 g) prepared as in Example 1 was placed in a three necked round bottom flask together with xylene (60 ml). The resulting slurry was heated to 90°C to obtain a homogeneous solution. The homogeneous solution was stirred at 90 °C for 2 h and insoluble particles (if any) were filtered and the solution was cooled slowly to 20-25 °C. After cooling, fine crystals formed and the resulting heterogeneous mixture was stirred at 20°C for 2 hours. Then, the slurry was filtered and washed with xylene (3ml) at 20°C. The filtered crystals were dried under vacuum at 60°C. The purity of the resulting crystalline product was about 98%, and the yield of recovered crystalline product was found to be about 85%.

[0135] The obtained crystals were analyzed by IR spectroscopy, X-RPD and DSC and found to be as figure 1 , figure 2 and image 3 Sulfentrazone crystalline modification I shown.

[0136] ...

Embodiment 3

[0141] Example 3 - Crystallization from diethyl ketone

[0142] A sample of sulfentrazone (5 g) prepared as in Example 1 was placed in a three necked round bottom flask together with diethyl ketone (35 ml). The resulting slurry was heated to 80°C to obtain a homogeneous solution. The resulting hot solution was stirred at 80 °C for 2 h and insoluble particles (if any) were filtered and the solution was slowly cooled to 20 °C. After cooling, fine crystals formed and the resulting heterogeneous mixture was stirred at 20°C for 2 hours. Then, the slurry was filtered, washed with diethyl ketone (3 ml) at 20°C, and dried at 50°C under vacuum. The resulting crystalline product was about 98% pure and was found to be recovered in about 85% yield.

[0143] The crystals were characterized as crystalline modification I of sulfentrazone using IR spectroscopy, X-ray powder diffraction and DSC as described in Example 2.

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Abstract

The invention describes a new crystalline form of sulfentrazone and its preparation process. The invention also describes the analyses of the crystal through various analytical methods and the use ofthe crystal to prepare stable agrochemical formulation. The novel crystal form is particularly suitable for use in herbicidal compositions and in the control of unwanted plant growth.

Description

[0001] Cross References to Related Applications [0002] This application claims priority from UK Patent Application No. 1608830.4, filed 19 May 2016, the contents of which are hereby incorporated by reference in their entirety. technical field [0003] This disclosure describes N-[2,4-dichloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2, Crystalline forms of 4-triazol-1-yl]phenyl]methanesulfonamide (sulfentrazone), processes for their preparation and their use in agrochemical formulations. Background technique [0004] N-[2,4-dichloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazole- 1-yl]phenyl]methanesulfonamide (sulfentrazone) is a member of the aryltriazolinone class of chemicals. Sulfentrazone is a pre- and post-emergence herbicide and is very effective against sedges in turfgrasses. It controls weeds through a generally known mode of action known as protoporphyrinogen oxidase (PPO) inhibition. The active ingredient sulfentrazone is ma...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/12A01N43/653A01P13/00
CPCA01N43/653C07D249/12
Inventor 詹姆斯·蒂莫西·布里斯托
Owner JIANGSU ROTAM CHEM
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