Novel 1,3,4-Oxadiazole-2-carbohydrazides as Prospective Agricultural Antifungal Agents Potentially Targeting Succinate Dehydrogenase

• DOI: 10.1021/acs.jafc.9b05942
• Publication Date: 2019-11-27T18:30:02Z
• Authors: Yuan-Yuan Wu; Wu-Bin Shao; Jian-Jun Zhu; Zhou-Qing Long; Li-Wei Liu; Pei-Yi Wang; Zhong Li; Song Yang
• Keywords: Gibberella zeae; EC50; Oxadiazole; Carbohydrazide

A novel simple 1,3,4-oxadiazole-2-carbohydrazide was reported to discover low-cost and versatile antifungal agents. Bioassay results suggested that a majority of the designed compounds were extremely bioactive against four types fungi two kinds oomycetes. This extreme bioactivity highlighted by applausive inhibitory effects 4b, 4h, 5c, 5g, 5h, 5i, 5m, 5p, 5t, 5v Gibberella zeae, affording EC50 values ranging from 0.486 0.799 μg/mL, which superior fluopyram (2.96 μg/mL) comparable those carbendazim (0.947 prochloraz (0.570 μg/mL). Meanwhile, 4g, 5f, 5t showed significant actions Fusarium oxysporum with 0.652, 0.706, 0.813, 0.925 respectively. Pharmacophore exploration N′-phenyl-1,3,4-oxadiazole-2-carbohydrazide pattern is necessary for bioactivity. Molecular docking 5h succinate dehydrogenase (SDH) indicated it can completely locate inside binding pocket via hydrogen-bonding hydrophobic interactions, revealing this framework might target SDH. result further verified effect on SDH activity. In addition, scanning electron microscopy patterns performed elucidate anti-G. zeae mechanism. Given these features, type suitable template future alternative inhibitors plant microbial infections.