Synthesis and biological evaluation of 4-methyl-1,2,3- thiadiazole-5-carboxaldehyde benzoyl hydrazone derivatives |
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Authors: | Jing-Peng Zhang Xiang-Yang Li Ya-Wen Dong Yao-Guo Qin Xin-Lu Li Bao-An Song Xin-Ling Yang |
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Institution: | a Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China;
b Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Research and Development Center for Fine Chemicals, Guizhou University, Guiyang 550025, China |
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Abstract: | To find new lead compounds with high biological activity, a series of novel 4-methyl-1,2,3-thiadiazole-5- carboxaldehyde benzoyl hydrazone derivatives were designed and synthesized. Their structures were confirmed by 1H NMR, 13C NMR, IR spectrum and elemental analysis. Preliminary bioassay indicated that the title compounds exhibited moderate to strong fungicidal activity against six fungi in vitro at 50 μg/mL. Moreover, some of the title compounds exhibited good curative activity against TMV in vivo at 500 μg/mL. The structure-activity relationship analysis of compounds against Valsa mali showed that compounds containing halogen at the para position on phenyl exhibited the best activity. Especially compound 8k showed broad spectrum fungicidal activities against Valsa mali, Botrytis cinerea, Pythium aphanidermatum, Rhizoctonia solani, Fusarium moniliforme and Alternaria solani with the EC50 values of 8.20, 24.42, 15.80, 40.53, 41.48, and 34.16 μg/mL, respectively. |
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Keywords: | 1 2 3-Thiadiazole Benzoyl hydrazone Synthesis Fungicidal activity Curative activity against TMV Structure-activity relationship |
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