Synthesis And Biological Activities Of Sulfonylureido Or Sulfonohydrazino Substituted Pyrrolidine-2,4-Dione Derivatives

Tenuazonic acid and its natural analogues with complex structure exhibited excellent bioactivities including antitumor, antivirus, fungicidal and herbicidal activities. Many tetramic acid analogues have been synthesized by the structure optimization of groups at pyrrolidine-2,4-dione, and many of them showed high bioactivity. In this article, sulfonylurea groups and sulfonylhydrazide groups were introduced to the 3-postion of tetramic acids to design and synthesize twenty-two 3-sulfonylureido or sulfonohydrazino substituted pyrrolidine-2,4-dione derivatives. These target compounds were evaluated for the herbicidal and fungicidal activities.Eight tetramic acid analogues were synthesized firstly. Then they were used as raw materials to react with substituted benzenesulfonylchlorides and toluenesulfonyl isocyanates respectively to give a class of sulfonohydrazino substituted tetramic acid derivatives and two classes of sulfonylureido substituted tetramic acid derivatives. These compounds included fourteen N’-((1-(1(5)-substituted-2,4-dioxopyrrolidin-3-ylidene)ethyl)benzenesulfonohydrazide compounds, five 3-(1-(1(5)-substituted-2,4-dioxopyrrolidin-3-ylidene)ethylamido)-1-(4-methylbenzenesulfonyl)urea and three 3-(1-(5-substituted-2,4-dioxopyrrolidin-3-ylidene)ethyl)-1-(4-methyl-benzenesulfonyl)-urea. The structures of the target compounds were confirmed by IR,1H NMR, MS and elemental analysis.The target compounds were evaluated for herbicidal activity asganist Brassica napus and Echinochloa crusgalli in vitro. Some of the compounds showed certain herbicidal activities aganist both of B. Campestris and E. Crusgalil at the concentration of 100 mg/L. The inhibitory rates of compounds A1, A7, C1, C2 and C3 aganist stem of Brassica napus were over 50%, in which the rates of C1, C2 and C3 reached 60%. But the target compounds showed low inhibitory rates of less than 50% aganist Echinochloa crusgalli roots and shoots.The fungicidal activities of all target compounds against Fusarium gramineaum, Botrytis cinerea, Rhizoctonia cerealis and Colletotrichum capsici were evaluated by mycelial growth rate method. At the concentration of 100 mg/L, all the compounds didn’t show obvious inhibition against the tested plant pathogens except the compound A7, its inhibitory rates against Botrytis cinerea and Rhizoctonia cerealis was over 50%, reached 57.3% and 52.3% respectively.