Synthesis process of primisulfuron-methy and other fluoric hebicide

A technology for fluoxulfuron-methyl and herbicides is applied in the field of synthesizing fluorine-containing herbicides, which can solve the problems of low yield and ozone layer destruction in the synthesis method, and achieve the effects of improving the yield and protecting the atmospheric environment.

Inactive Publication Date: 2003-08-20
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AI-Extracted Technical Summary

Problems solved by technology

[0005] The purpose of the present invention is to solve the problem of existing flurisulfuron-methyl, fluroxyzin, ET 751 The synthetic method of such fluorine-containing herbicides has the problem that the ozone layer...
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The synthesis process of primisulfuron-methyl and other fluoric herbicide incldues the reaction between fluorosulfuryl ethanoyl difluoride as fluorinating reagent and aza compound precurser in the molar ratio of 1.5-2.5 to 1 while adding polar compound as solvent and salt as catalyst at 20-80 deg.c for 2-4 hr; filtering; evaporating filtrate and washing residue with acid or alkali solution; and purification of the coarse product to obtain fluoric herbicide product or intermediate, which may be further produced into fluoric herbicide through available technological process. Using fluorosulfuryl ethanoyl difluoride, rather than freon, as fluorinating reagent has high yield and no damage to ozone layer of atmosphere.

Application Domain

BiocideAnimal repellants +1

Technology Topic

SolventChemistry +5


  • Experimental program(1)

Example Embodiment

[0012] Embodiment: For the key intermediate 2-amino of synthetic flurimsulfuron methyl, the reaction of 4,6 bis (difluoromethoxy) pyrimidines:
[0013] The specific operation is as follows, 1.27g (0.01mol) of 2-amino, 4,6-dihydroxypyrimidine, 0.007mol of Cu + catalyst while adding 30ml of CH 3 CN was used as a solvent, put it into the reflux tube and a thermometer, filled with nitrogen gas protection, added dropwise 4.5g (0.025mol) fluorosulfone difluoroacetic acid, raised the temperature to 50°C, and reacted for 3 hours. After the reaction was completed, filter, and evaporate the filtrate to its solvent. After cooling, a solid was precipitated, and the resulting solid was washed with 5% NaOH solution to obtain a crude product, which was separated by column chromatography (developing solvent: V (petroleum ether): V (ethyl acetate) = 5: 1) to obtain a white needle. 0.4 g of solid crystals, yield 18%. The obtained crystals were examined: m.p, 68~69°C; H-NMR, δ: (CDCl 3 /TMS), 5.10 (S, 2H, NH 2 ); 5.80 (S, H, CH), 7.38 (t, 2H, CHF 2 );1 9 F-NMR, δ: (CDCl 3 )5.85(t, 2F, CF 2 H), MS, M/z: 227 (M + ), 177 (M + -CF 2 ), 161 (M + -OCF 2 ), 127 (M + -2CF 2 ), 68 (HOCF 2 H), 51 (CF 2 h).
[0014] Elemental analysis: (theory/experiment): C: 31.73/31.65, H: 2.22/2.14, N: 18.5/18.58.
[0015] After analysis, the resulting product is 2-amino, 4,6-bis(difluoromethoxy)pyrimidine, then react it with o-methoxyformylbenzenesulfonyl isocyanate, and use acetonitrile as solvent to obtain the final Product Fluorosulfuron-methyl herbicide.


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