Design, Synthesis And Biological Activity Of Novel Sulfonylurea Oxazolidines

A series of N- [(p-methylphenyl)sulfonyl]-1,3-oxazolidine-3-carboxamide 4 was synthesized by cycloaddition and acylation reaction with alkamine, ketones, and p-methylbenzenesulfonyl isocyanate as the starting materials.The structures of all the compounds were characterized by IR, 1 H NMR, 13 C NMR, MS, and elemental analysis.The configuration of 4d was determined by X-ray crystallography.The preliminary biological test showed that all compounds could protect maize against injury caused by chlorsulfuron to certain extent.The sulfonylurea oxazolidines were possible acted as antagonists of sulfonylureas herbicides at target enzyme pocket site by docking analysis.Sulfonylureas (SUs) compounds have a wide range of practical applications such as insecticides, 1 antimicrobial agents, 2 anticancer agents, 3 as well as herbicides. 4SUs are the very popular herbicides used for controlling a range of weeds and some grasses in a variety of crops and vegetables because of their good herbicidal activity, low mammalian toxicity, high selectivity, and benign environmental activity.However their phytotoxicities and the residues to succeeding crops have caused some concerns.Some sulfonylurea herbicides (such as Chlorsulfuron, Metsulfuron, Chlorimuron-ethyl) are long residual herbicides, and persistent in soil which is poisonous to susceptive crops. 5More and more novel safeners for SUs herbicides have been commercialized, such as Dimepiperate, Dymron, and Cyprosulfamide (Scheme 1). 6ructure-activity relationship theory (SAR) are very important in the search for bioactive materials because it provides useful molecular structure information that are necessary for the target bioactivity. 7se on the SAR, active substructure combination, and bioisosteric replacement, the novel aniline derivatives of Chlorothalonil was designed and synthesized by substitution of Cl atom on Chlorothalonil with aryl amine moiety of Fluazinam, another commercially available agent (Scheme 2). 8Recently many