2-硫代-1,3-噻唑烷-3-甲酸酯的合成及生物活性

Synthesis and Biological Activities of 2-Thio-1,3-thiazolidine-3-carboxylates

为了寻找新的含噻唑杂环的先导化合物,利用2-硫代-1,3-噻唑烷与氯甲酸酯在三乙胺存在下进行缩合反应,合成了11个2-硫代-1,3-噻唑烷-3-甲酸酯类化合物,并利用1HNMR、IR、MS及元素分析对其结构进行了表征;通过X-ray单晶衍射测定了2-硫代-1,3-噻唑烷-3-甲酸苯酯(3i)的晶体结构,证实反应产物为硫酮式而非硫酯式结构。初步生物活性试验结果表明,在试验浓度下部分目标化合物具有一定的杀菌和杀虫活性,其中3c、3f、3h、3k在500mg/L下对棉红蜘蛛Tetranychus urticae的致死率均在70%以上。

In order to find new thiazole-heterocycle lead compounds, eleven 2-thio-1,3-thiazolidine-3- carboxylates were synthesized from a condensation reaction of 2-thio-1,3-thiazolidine and chloroformates in presence of Et3N. Their structures were confirmed by ^1H NMR ,IR ,MS and elemental analysis. The crystal structure of phenyl 2-thio-1,3-thiazolidine-3-carboxylate （3i） were determined by X-ray diffraction analysis, and the structure of the condensation products of 2-thio-1,3-thiazolidine and chloroformates were proven to be 2-thio-1, 3-thiazolidine-3-carboxylate rather than the ester of mercaptothiazoline. The preliminary bioassay showed that compounds of 3 series exhibited certain fungicidal and insecticidal activities, and compounds 3c, 3f, 3h, 3k showed inhibitory activities （with inhibition rate above 70% ） against Tetranychus urticae at the concentration of 500 mg/L.