Synthesis method of pyrazosulfuron-ethyl intermediate 4-ethoxycarbonyl-5-sulfamine-1-methylpyrazole
The invention discloses a synthesis method of a pyrazosulfuron-ethyl intermediate 4-ethoxycarbonyl-5-sulfamine-1-methylpyrazole. The method comprises the following steps: (1) performing condensation reaction on 4-ethoxycarbonyl-5-hydroxyl-1-methylpyrazole and dimethylthiocarbamoyl chloride to obtain 4-ethoxycarbonyl-5-dimethylthio carbamoyl oxy-1-methylpyrazole; (2) performing transposition rearrangement reaction on the 4-ethoxycarbonyl-5-dimethylthio carbamoyl oxy-1-methylpyrazole to obtain 4-ethoxycarbonyl-5-dimethyl carbamoyl sulfenyl-1-methylpyrazole; (3) performing chlorosulfonation reaction on the 4-ethoxycarbonyl-5-dimethyl carbamoyl sulfenyl-1-methylpyrazole and chlorine to obtain 4-ethoxycarbonyl-5-sulfonyl chloride-1-methylpyrazole; (4) performing ammoniation reaction on the 4-ethoxycarbonyl-5-sulfonyl chloride-1-methylpyrazole and ammonium hydroxide to obtain the 4-ethoxycarbonyl-5-sulfamine-1-methylpyrazole. The method is less in environment pollution, particularly high in product purity, and high in total yield.
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(2017/07/20)
Transformation kinetics and mechanism of the sulfonylurea herbicides pyrazosulfuron ethyl and halosulfuron methyl in aqueous solutions
Pyrazosulfuron ethyl (PE) and halosulfuron methyl (HM) are two new highly active sulfonylurea herbicides that have been widely used for weed control in a variety of vegetables and other crops. These two herbicides have similar molecular structures, differing only in the substitutions on the pyrazole ring. Chemical hydrolysis is a primary process affecting the environmental fate of sulfonylurea pesticides. The hydrolytic transformation kinetics of PE and HM were investigated as a function of pH and temperature. For both herbicides, the hydrolysis rate was pH-dependent and increased with increasing temperature. The hydrolysis of both sulfonylureas was much faster in acidic or basic media than under neutral conditions. Identification of hydrolytic products by liquid chromatography-mass spectrometry (LC-MS) suggested that both PE and HM were subject to cleavage and contraction of the sulfonylurea bridge. The hydrolysis rate of HM was significantly higher than that of PE in alkaline solutions, despite their structural similarity. A chlorine substitution on HM's pyrazole ring makes HM more susceptible to bridge contraction than PE under basic conditions. The hydrolysis of HM and PE was relatively unaffected by the presence of cyclic oligosaccharides (cyclodextrins), indicating that natural OH-containing organic compounds occurring in aquatic environments may have little impact on the transformation of these sulfonylurea herbicides.
Zheng, Wei,Yates, Scott R.,Papiernik, Sharon K.
experimental part
p. 7367 - 7372
(2010/05/18)
Sulfonylureas as dual acting agents - Synthesis and biological activity
2-Amino-5-aryl/alkyl-1,3,4-thiadiazoles 3a-e were used as intermediates in the synthesis of some 1,3-substituted urea derivatives 5a-o to evaluate their antidiabetic activity as well as antibacterial activity. The obtained compounds exhibited marginal activity against the animal models and the selected microorganisms.
Chavan, Ameya A.,Pai, Nandini R.
p. 771 - 777
(2008/03/11)
A facile synthesis of pyrazole-5-sulfonamide derivatives [1]
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Yamamoto,Sato,Morimoto,Makino
p. 1849 - 1852
(2007/10/02)
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