Synthesis and Fungicidal Activity of Simple Structural 1,3-Thiazolidine-2-Thione Derivatives
Synthesis and Fungicidal Activity of Simple Structural 1,3-Thiazolidine-2-Thione Derivatives
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简单结构1,3-噻唑烷-2-硫酮衍生物的合成及其杀菌活性
DOI：
10.1080/10426507.2014.931399
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发表时间：
2015
期刊：
影响因子：
--
通讯作者：
Xu Jiaxi
中科院分区：
文献类型：
--
作者：
Chen Ning;Du Hongguang;Liu Weidong;Wang Shanshan;Li Xinyao;Xu Jiaxi
摘要以邻氨基醇为原料，通过两步反应合成了一系列结构简单、在S-、N-、4-和5-位上具有不同取代基的1，3-噻唑烷-2-酮衍生物，并对其进行了抗真菌活性筛选。生物活性测定结果表明，部分噻唑烷-2-酮衍生物对辣椒疫霉、G. zeae、玉米S. sclerotiorum，A. alternata，B. cinerea或R.索拉尼构效关系分析表明，N-酰基取代和4-烷基取代均能提高化合物的抗真菌活性。值得注意的是，4-异丙基-N-丙酰基噻唑烷-2-酮显示出优异的抗B活性。cinerea和G. 4-异丁基-N-丙酰基噻唑烷-2-酮对玉米赤霉菌的IC_（50）分别为3.7 μg/mL和6.5 μg/mL。solani，S. sclerotiorum和G.玉米的IC 50值分别为1.0 μg/mL、12.1 μg/mL和11.0 μg/mL。
GRAPHICAL ABSTRACT Abstract A series of simple structural 1,3-thiazolidine-2-thione derivatives with various substituents on the S-, N-, 4-, and 5-positions was synthesized with high yields from various vicinal amino alcohols via two steps and screened for their antifungal activity. Bioassay results reveal that some thiazolidine-2-thione derivatives show strong antifungal activities against P. capsici, G. zeae, S. sclerotiorum, A. alternata, B. cinerea, or R. solani. The SAR analysis indicates that N-acyl substituted and 4-alkyl substituents can enhance the antifungal activity. Notably, 4-isopropyl-N-propionylthiazoldine-2-thione shows excellent activity against B. cinerea and G. zeae with IC50 values at 3.7 μg/mL and 6.5 μg/mL, respectively, and 4-isobutyl-N-propionylthiazoldine-2-thione shows remarkable fungicidal activity against R. solani, S. sclerotiorum, and G. zeae with IC50 values at 1.0 μg/mL, 12.1 μg/mL, and 11.0 μg/mL, respectively.