Process for synthesizing triketone herbicide cyclic sulcotrione

A technology of sulfotrione and synthesis process, which is applied in the field of preparation of pesticide technical materials, can solve the problems of high production cost, expensive brominating agent, difficult to handle mercaptan, etc., and achieve reduction of production cost, shortening of reaction steps and time, The effect of production process safety

Inactive Publication Date: 2015-01-21
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The synthetic route that prior art adopts has following shortcoming: (1) adopt sodium methyl mercaptide smell relatively big, the mercaptan in the waste water is difficult to handle, cause environmental pollution; (2) production cost is too high; (3) adopt N-bromine Succinimide as brominating agent, which is expensive

Method used

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  • Process for synthesizing triketone herbicide cyclic sulcotrione
  • Process for synthesizing triketone herbicide cyclic sulcotrione
  • Process for synthesizing triketone herbicide cyclic sulcotrione

Examples

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Embodiment 1

[0033] 1. Synthesis of 2-chloro-6-methylsulfonyltoluene

[0034]

[0035] Add 25.3g (0.2mol) of 2-chlorotoluene, 40.5g (0.3mol) of anhydrous aluminum trichloride and 1,2-dichloroethane into a 500ml four-necked reaction flask equipped with a stirrer, a thermometer and a reflux condenser 150ml of alkane, cooled to 5°C, then added dropwise 25.25g (0.22mol) of methanesulfonyl chloride, the dropping temperature did not exceed 10°C, after the dropwise addition was completed, it was raised to room temperature and continued to react for 10h, followed by LC (liquid chromatography) until the reaction was complete , the reactants were poured into ice water, the organic layer was separated, the aqueous layer was extracted with 1,2-dichloromethane, the organic phases were combined and concentrated to obtain 28.6 g of light yellow solid, with a yield of 84%.

[0036] 2. 2-Chloro-3-acetyl-6-methylsulfonyltoluene

[0037]

[0038] Add 34.0 g (0.2 mol) of 2-chloro-6-methylsulfonyltoluen...

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Abstract

The invention relates to a process for synthesizing triketone herbicide cyclic sulcotrione. The method comprises the following steps: (1) synthesizing 2-chloro-6-methylsulfonyl methylbenzene; (2) synthesizing 2-chloro-3-acetyl-6-methylsulfonyl methylbenzene; (3) synthesizing 2-chloro-3-methyl-4-methylsulfonyl benzoic acid; (4) synthesizing methyl 2-chloro-3-methyl-4-methylsulfonyl benzoate; (5) synthesizing methyl 2-chloro-3-bromomethyl-4-methylsulfonyl benzoate; (6) synthesizing 2-chloro-3-(2,2,2-trifluoroethyoxy)methyl-4-methylsulfonyl benzoic acid; (7) synthesizing 2-chloro-3-(2,2,2-trifluoroethyoxy)methyl-4-methylsulfonyl benzoic acid 3-oxo-1-cyclohexene ester; and (8) synthesizing cyclic sulcotrione. The process disclosed by the invention has the beneficial effects that the reaction steps are reduced, the reaction time is shortened, and the yield of intermediates is improved; the reaction conditions are mild and safe; and the cost is reduced.

Description

technical field [0001] The invention belongs to the field of preparation of pesticide technical materials, and in particular relates to a synthesis process of a triketone herbicide sulfotrione. Background technique [0002] Herbicide Tembotrione, chemical name: 2-(2-chloro-4-methylsulfonyl-3-[(2,2,2-trifluoroethoxy)methyl]benzoyl)cyclohexyl Alkane-1,3-dione. The triketone cornfield herbicide developed by Bayer in 2007 has a higher activity than nitrosulfone and mesotrione currently on the market, and is safe for crops. It has a strong killing effect on a variety of weeds, has no residual activity, has strong resistance to rain erosion, and has a wide spectrum of weeding. It can effectively control Capsicum spp. weeds. [0003] The synthetic route that prior art adopts has following shortcoming: (1) adopt sodium methyl mercaptide smell relatively big, the mercaptan in the waste water is difficult to handle, cause environmental pollution; (2) production cost is too high; (3...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C317/24C07C315/04
Inventor 刘安昌贺晓露冯佳丽
Owner WUHAN INSTITUTE OF TECHNOLOGY
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