高等学校化学学报2016，Vol.37Issue(9)：1636-1642,7.DOI:10.7503/cjcu20160257
苯环5位取代磺酰脲类化合物的水解动力学及三维定量构效关系初步研究
Kinetics of the Chemical Hydrolysis and 3 D-QSAR Study of 5-Substituted Benzenesulfonylurea Compounds
摘要
Abstract
The hydrolysis of 9 new 5-substituted benzenesulfonylurea compounds with good herbicidal activity under acidic, neutral and alkaline pH conditions was investigated in laboratory studies. HPLC-MS was used to identify degradates and to study the pathway of hydrolysis. Comparative molecular field analysis ( CoMFA ) method was applied to the study of the three-dimensional quantitative structure activity relationship ( 3 D-QSAR) on the relationship between the structure of the 5-substituted benzenesulfonylurea compounds and the half-life of hydrolysis. The results showed that the hydrolytic degradation of 5-substituted benzenesulfonylurea followed first-order kinetics. It was easier to be hydrolyzed in acid buffer solutions. Acid-catalyzed cleavage of the sulfonylurea bridge was the first step of degradation, and thus produces 5-substituted benzene sulfonamide and amino-heterocyclic. Amide group further hydrolyzed producing the compound c(6-amino saccharin) and d( saccharin) . The 5-substituted benzenesulfonylurea compounds hydrolyzed significantly faster than the parent compounds, Monosulfuron-methyl and Metsulfuron-methyl, under the same conditions. The hydrolysis rate decreased with the increase of the number of alkyl carbon atoms on the amide group and the increase of the volume of the alkyl group. The CoMFA model was able to predict the hydrolysis half-life of this series of compounds.关键词
5位取代苯磺酰脲类化合物/水解/半衰期/比较分子力场模型/三维定量构效关系Key words
5-Substituted benzenesulfonylurea compound/Hydrolysis/Half-life/Comparative molecular field analysis(CoMFA) model/Three-dimensional quantitative structure activity relationship(3D-QSAR)分类
化学化工引用本文复制引用
王美怡,马翼,王海英,曹刚,李正名..苯环5位取代磺酰脲类化合物的水解动力学及三维定量构效关系初步研究[J].高等学校化学学报,2016,37(9):1636-1642,7.基金项目
国家自然科学基金(批准号:21262001)资助. Supported by the National Natural Science Foundation of China(No.21262001) （批准号:21262001）
