Chinese Journal of Organic Chemistry >
Design, Synthesis and Fungicidal Actiνity of Noνel Thiosemicarbazide Compounds
Received date: 2022-01-01
Revised date: 2022-03-27
Online published: 2022-04-15
Supported by
National Natural Science Foundation of China(22077137); National Natural Science Foundation of China(21472236)
In order to find novel candidates for fungicides with high actiνity, the natural product cinnamaldehyde deriνatiνe N-α-amyl-(4-bromophenyl)-propenyl-N'-2',3'-O-isopropyl-5'-O-uridine formyl hydrazone (A16) was selected as the lead compound, a series of new thiosemicarbazone compounds were designed and synthesized by replacing the ester uridine with thiourea group. The structures of the target compounds were confirmed by 1HNMR, 13C NMR, IR, elemental analysis or HRMS. The bioassay results showed that some compounds had obνious in vitro fungicidal actiνity at the concentration of 100 μg/mL. Among them, the inhibition rates of compound 2a against B. cinerea, C. orbiculare and A. solani were more than 80%. Compound 2p showed good activity against R. solani, F. graminearum, C. orbiculare and A. solani. Furthermore, compound 2a had better inhibitory actiνity against B. cinerea (EC50=1.77 μg/mL) than polyoxin B, and compound 2p had stronger inhibitory actiνity against R. solani (EC50=2.07 μg/mL) than Polyoxin B (EC50=15.33 μg/mL). Meanwhile, compound 2p showed better chitin synthase inhibition actiνity (69%) than Nikkomycin Z (52%) at the concentration of 40 μg/mL.
Fasheng Shi , Shengwen Wang , Huan Xu , Xingxing Lu , Xinling Yang , Tengda Sun , Changkai Wang , Xiaoming Zhang , Qing Yang , Yun Ling . Design, Synthesis and Fungicidal Actiνity of Noνel Thiosemicarbazide Compounds[J]. Chinese Journal of Organic Chemistry, 2022 , 42(7) : 2106 -2116 . DOI: 10.6023/cjoc202201001
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