Design, Synthesis, and Biological Evaluation of Novel 1,3,4-Thiadiazolylpyrazolines Compounds Containing Ferrocene

Article abstract of DOI:10.1002/jhet.3238

The synthesis of 1,3,4-thiadiazole skeleton compounds exhibiting high fungicidal activities has been demonstrated. Thirteen novel 1,3,4-thiadiazolyl-pyrazolines compounds containing ferrocene were designed and synthesized from the ferrocenylchalcones intermediates 3a–3m and the 2-hydrazino-5-phenyl-1,3,4-thiadiazole intermediate 8. All compounds were characterized by ¹H NMR, ¹³C NMR, FT-IR spectra, and HR-MS, and the structure of one of the new compounds N-(4-phenyl-1,3,4-thiadiazol-2-yl)-3-ferrocenyl-5-phenyl-pyrazoline 9a was further determined by X-ray diffraction analysis. The preliminary results of a biological activity assay indicated that all the title compounds exhibited significant fungicidal activities against Pythium solani, Gibberella saubinetii, and Gibberella nicotiancola. Furthermore, compounds 9e and 9h displayed even higher fungicidal activities against the three fungal species compared with the control drug pyraclostrobin.