Preparation method of sulfonyl phenylurea herbicide safener

A technology of sulfonylurea and herbicide, which is applied in the field of preparation of sulfonylurea herbicide safener, can solve the problems of large amount of catalyst and organic solvent, complex reaction process, serious environmental pollution, etc., and achieve the solution of environmental pollution and potential safety hazards, simplification of the reaction process, and less pollution

Pending Publication Date: 2022-01-18
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The raw materials used in this method, such as phenyl chloroformate and 2-methoxybenzoyl chloride, are irritating and highly toxic items, the reaction process is complicated, the amount of catalyst and organic solvent is large, the cost is high, there are many three wastes, serious environmental pollution, and it is not suitable for my country's current environmental protection needs

Method used

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  • Preparation method of sulfonyl phenylurea herbicide safener

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1 Synthesis of phenyl 4-sulfamoylphenylcarbamate

[0027] Add p-aminobenzenesulfonamide (50g, 0.29mol), diphenyl carbonate (65.3g, 0.30mol), isobutyric acid (2.6g, 0.029mol), methanol (500ML) into the reaction flask, and heat to 65°C , reflux reaction for 48 hours, cooled to room temperature after the reaction, and filtered to obtain 72.1 g of phenyl 4-sulfamoylphenylcarbamate, yield 85.1%, melting point: 220.3-222.8°C.

example 2

[0028] Example 2 Synthesis of 4-(3-methylureido)benzenesulfonamide

[0029] Add 4-sulfamoylphenylcarbamate phenyl ester (30 grams, 0.1mol) and ethanol (200ML) into the reactor, heat to 78°C, add methylamine ethanol solution dropwise, react at 78°C for 6 hours, and react After cooling to room temperature, 21.5 g of 4-(3-methylureido)benzenesulfonamide was obtained by filtration, with a yield of 93.8% and a melting point of 210.8-212.7°C.

example 3

[0030] Example 3 Synthesis of 2-methoxy-N-{[4-(3-methylureido)phenyl]sulfonyl}benzamide

[0031] Add 4-(3-methylureido)benzenesulfonamide (15 grams, 0.065mol), o-methoxybenzoic acid (11.9 grams, 0.08mol), 4-dimethylaminopyridine (0.8 grams, 0.007mol), dicyclohexylcarbodiimide (27.0g, 0.13mol), N,N-dimethylformamide (200ML), reacted at -10°C for 36 hours, filtered, recovered the organic solvent, and weighed with ethanol 20.9 g of the product 2-methoxy-N-{[4-(3-methylureido)phenyl]sulfonyl}benzamide was obtained by crystallization, the yield was 88.2%, and the melting point was 236.2-238.4°C.

[0032] 1 H NMR (300MHz, DMSO) δ11.70(s, 1H), 9.11(s, 1H), 7.83(d, J=8.9Hz, 2H), 7.62(d, J=8.9Hz, 2H), 7.50(m ,J=9.0,7.4,1.8Hz,1H),7.39(dd,J=7.6,1.7Hz,1H),7.12(d,J=8.3Hz,1H),6.99(t,J=7.5Hz,1H) ,6.24(q,J=4.3Hz,1H),3.83(s,3H),2.66(d,J=4.6Hz,3H).

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Abstract

The invention belongs to the technical field of herbicide safeners and relates to a preparation method of a sulfonyl phenylurea herbicide safener. The method comprises the following steps of: adding sulfanilamide, diphenyl carbonate and an organic solvent into a reactor, making the material to undergo a reaction under the action of a catalyst, and performing cooling and filtering after the reaction is finished to obtain 4-sulfamoyl phenyl carbamate; adding the 4-sulfamoyl phenyl carbamate and a solvent into a reactor for reaction, cooling after the reaction is finished, and filtering to obtain 4-(3-methylureido) benzenesulfonamide; adding the 4-(3-methylureido) benzenesulfonamide, an organic solvent, o-methoxybenzoic acid, a catalyst and a condensing agent into the reactor, performing a reaction at room temperature, performing filtering, recovering the organic solvent, and recrystallizing with low-fat alcohol to obtain the product 2-methoxy-N-{[4-(3-methylureido) phenyl] sulfonyl} benzamide. The preparation method is simple in process, convenient to operate, high in yield, low in cost, green, safe and less in pollution.

Description

technical field [0001] The invention relates to the technical field of herbicide safeners, in particular to a preparation method of sulfonylurea herbicide safeners. Background technique [0002] Herbicide safeners protect crops from herbicide damage without affecting their activity on the target crop. Herbicide safeners can enhance the selectivity of herbicides on weeds and crops, and can be mixed with herbicides or used as seed treatments before sowing. Repeated applications or uneven spraying can lead to local overdose of herbicides, and changes in soil and climate conditions can lead to excessive herbicide concentrations recommended for use. In order to solve the problem of herbicide phytotoxicity and residual phytotoxicity, many compounds have been developed as herbicide safeners, which can selectively protect crops and reduce the sensitivity of crops to herbicides without reducing the activity of herbicides. This increases crop safety and improves weed control. Howev...

Claims

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Application Information

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IPC IPC(8): C07C303/40C07C311/47C07C311/51
CPCC07C303/40C07C311/47C07C311/51
Inventor 徐德锋叶凯冯文豪祁久乐徐斌陈竞雷胡航陈海群
Owner CHANGZHOU UNIV
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