Chinese Journal of Organic Chemistry >
Design, Synthesis and Fungicidal Activity of Novel Piperidine Containing Cinnamaldehyde Thiosemicarbazide Derivatives
Received date: 2019-03-17
Revised date: 2019-04-18
Online published: 2019-05-21
Supported by
Project supported by the National Natural Science Foundation of China(No. 21672258)
In order to find new lead compound with higher fungicidal activity, a series of novel cinnamaldehyde thio- semicarbazone derivatives were designed and synthesized according to scaffold hopping strategy, based on the lead of the thiosemicarbazide derivatives containing piperidine discovered in our preliminary studies. Their structures were confirmed by 1H NMR, 13C NMR, IR, elemental analysis or HRMS. The bioassay results indicated that some compounds exhibited excellent fungicidal activities. In particular, N'-((1E,2E)-3-(4-chlorophenyl)allylidene)piperidine-1-carbothiohydrazide (3a) and N'-((1E, 2E)-3-phenylallylidene)piperidine-1-carbothiohydrazide (3p) showed above 95% inhibitory rate against Cytospora sp, S. sclerotiorum, P. aphanidermatum and T. cucumeris at 50 μg/mL with EC50 values lower than 10 μg/mL. The preliminary structure-activity relationship indicated that cinnamaldehyde contributes more to the bioactivity than benzaldehyde.
Xuebo Zhang, , Hangyu Ma, , Tengda Sun, , Peng Lei, , Xinling Yang, , Xiaoming Zhang, , Yun Ling, . Design, Synthesis and Fungicidal Activity of Novel Piperidine Containing Cinnamaldehyde Thiosemicarbazide Derivatives[J]. Chinese Journal of Organic Chemistry, 2019 , 39(10) : 2965 -2972 . DOI: 10.6023/cjoc201903031
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