Design, Synthesis and Antifungal/Nematicidal Activity of Novel 1,2,4-Oxadiazole Derivatives Containing Amide Fragments

• Published in: International journal of molecular sciences Vol. 23; no. 3; p. 1596
• Main Authors: Liu, Dan, Luo, Ling, Wang, Zhengxing, Ma, Xiaoyun, Gan, Xiuhai
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 29-01-2022; MDPI
• Subjects: 1,2,4-oxadiazole; Amides - chemistry; Antifungal activity; Antifungal agents; Antifungal Agents - chemical synthesis; Antifungal Agents - chemistry; Antifungal Agents - pharmacology; Ascomycota - drug effects; Ascomycota - growth & development; Ascomycota - metabolism; Bioassays; Cell Line; Crop diseases; Cytotoxicity; Dehydrogenases; Drug Design; Fragments; Fungal Proteins - chemistry; Fungal Proteins - metabolism; Fungi; Fungicides; Humans; Hyphae; Hyphae - drug effects; Hyphae - growth & development; Hyphae - metabolism; Microbial Viability - drug effects; Models, Molecular; Molecular docking; Molecular Structure; nematicidal activity; Nematodes; Oxadiazoles; Oxadiazoles - chemical synthesis; Oxadiazoles - chemistry; Oxadiazoles - pharmacology; Pesticides; Plant diseases; Plants - drug effects; Plants - microbiology; Plants - parasitology; Protein Conformation; Scanning electron microscopy; Structure-Activity Relationship; Succinate dehydrogenase; Succinate Dehydrogenase - chemistry; Succinate Dehydrogenase - metabolism; 1,2,4-oxadiazole; antifungal activity; nematicidal activity; succinate dehydrogenase
• ISSN: 1422-0067; 1661-6596; 1422-0067
• DOI: 10.3390/ijms23031596

Plant diseases that are caused by fungi and nematodes have become increasingly serious in recent years. However, there are few pesticide chemicals that can be used for the joint control of fungi and nematodes on the market. To solve this problem, a series of novel 1,2,4-oxadiazole derivatives containing amide fragments were designed and synthesized. Additionally, the bioassays revealed that the compound
demonstrated excellent antifungal activity against
(
) in vitro, and the EC
value of that was 2.9 μg/mL, which is comparable with commonly used fungicides thifluzamide and fluopyram. Meanwhile,
demonstrated excellent curative and protective activity against
-infected cole in vivo. The scanning electron microscopy results showed that the hyphae of
treated with
became abnormally collapsed and shriveled, thereby inhibiting the growth of the hyphae. Furthermore,
exhibited favorable inhibition against the succinate dehydrogenase (SDH) of the
(IC
= 12.5 μg/mL), and the combination mode and binding ability between compound
and SDH were confirmed by molecular docking. In addition, compound
showed excellent nematicidal activity against
at 200 μg/mL, the corrected mortality rate was 93.2%, which is higher than that of tioxazafen.