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Polymorphs of herbicidal sulfonamides

A polymorphic, sulfentrazone technology, applied in the field of polymorphic forms of herbicidal sulfonamide, can solve problems such as solvent exposure

Active Publication Date: 2019-08-06
FMC CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The presence of entrapped solvents in Sulfentralam Technical Grade may create exposure issues in subsequent processing and / or use of Sulfentralam Technical Grade

Method used

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  • Polymorphs of herbicidal sulfonamides
  • Polymorphs of herbicidal sulfonamides
  • Polymorphs of herbicidal sulfonamides

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0145] Preparation of polymorphs

[0146] Sulfentrazone (Formula (I)) is generally prepared as described in US Patent 7,169,952.

[0147]The following procedure is taken from U.S. Patent 7,169,952 and is a typical procedure used herein for the preparation of technical grade sulfentrazone (Form 2), where possible variations are related to processing conditions such as batch size, time, temperature, etc.:

[0148] This example illustrates the preparation of N-[2,4-dichloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo- Scheme for 1H-1,2,4-triazol-1-yl]phenyl]methanesulfonamide.

[0149] Under a nitrogen atmosphere, 262 lbs of 16 wt% 1-(5-amino-2,4-dichlorophenyl)-4,5-dihydro-4-difluoromethane was charged to a 50-gallon glass-lined reactor A solution of 3-methyl-1,2,4-triazol-5(1H)-one in toluene. The solution was stirred and heated to about 105-115°C. During heating, the nitrogen atmosphere was stopped and the reaction vessel was sealed under a vacuum of about 750-780 mmH...

preparation Embodiment

[0165] The sulfentrazone-1 obtained as above was formulated into a suspension concentrate and a wettable powder.

[0166] 3a. Preparation of formulations of sulfentrazone-1 in the form of suspension concentrates

Embodiment 1

[0168]

[0169]

[0170] Mix water with Tergitol TM XD and Tergitol TM XH mix until they are completely dissolved. Join Dextrol TM OC-180. The mixture was transferred to an attritor and sulfentrazone-1 was added. The slurry was milled using 0.5 mm stainless steel beads until the particle size was reduced to 13 μd90. The milled slurry is separated from the grinding media and the slurried in propylene glycol M and GXL is added to the mix.

[0171] 3b. Formulation of sulfentrazone-1 in wettable powder form

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Abstract

Solid polymorphic forms of sulfentrazone are described. Particularly, a new polymorphic form of sulfentrazone is described herein as sulfentrazone-1, having surprising property advantages over technical sulfentrazone. Processes for the preparation of sulfentrazone-1, herbicidal compositions comprising sulfentrazone-1, and methods of its use are described.

Description

[0001] Field of invention [0002] The present invention relates to novel solid polymorphs of N-(substituted phenyl)sulfonamides, processes for their preparation, compositions containing the solid forms and their use in herbicides. Background technique [0003] It is known in the art that some N-(substituted phenyl)sulfonamides can have insecticidal activity, and these compounds can be used in the preparation of certain pesticides. For example, use N-[2,4-dichloro-5-[4-(difluoromethyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4- Triazol-1-yl]phenyl]methanesulfonamide is disclosed as a herbicide (described below as Formula I and commonly referred to as sulfentrazone) in US Patent 4,818,275. U.S. Patents 4,818,275 and 7,169,952 disclose methods for preparing sulfentrazone. Commercial products incorporating sulfentrazone are prepared using technical grade materials containing a mixture of polycrystalline forms of sulfentrazone. Technical grade saflufentrazone materials may often incl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A01N43/653A01N37/18A01N33/18
CPCA01N43/653A01N25/12C07B2200/13C07D249/12
Inventor P·尼科尔森K·考夫曼
Owner FMC CORP
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