The development of new green fungicides is an effective way to solve the resistance of agricultural pathogens and plays an important role in promoting high-quality and sustainable development of modern agriculture. In this project, a series of aryloxy-, arylthio-, and arylamino-containing acethydrazide derivatives were designed, synthesized, and characterized by ¹H nuclear magnetic resonance (NMR), ¹³C NMR, and high-resolution mass spectrometry (HRMS). The fungicidal bioassays indicated that some compounds showed excellent and broad-spectrum fungicidal activity, and the structure–activity relationship was discussed. The in vivo fungicidal activity demonstrated that compounds C4 and D8 exhibited good preventative effects against Fusarium graminearum infecting wheat leaves, of which the preventative activity of compound D8 was almost equal to that of the positive agents. Transmission electron microscopy (TEM) observation revealed that the plasma membrane in the C4-treated F. graminearum hyphal cells was severely contracted and separated with the cell wall, coupling with the visible lysosomes and the disappeared cytoplasm and organelles, which may be the reasons for the shriveled and even ruptured hyphae observed by scanning electron microscopy (SEM). Subsequently, transcriptomics and metabolomics were performed to further elucidate the fungicidal mechanism. The regulatory networks of differential genes and metabolites in plasma membrane-related sphingolipid metabolism, linoleic acid metabolism, α-linoleic acid metabolism, and arachidonic acid metabolism were constructed and elaborated. Additionally, preliminary investigation of seeding growth suggested that compounds C4 and D8 may have different degrees of influence on the growth indicators of wheat seedlings; however, this effect may be negligible as the plant grows.

中文翻译：

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发现含有芳氧基、芳硫基和芳氨基的乙酰肼作为杀真菌剂

开发新型绿色杀菌剂是解决农业病原菌抗药性的有效途径，对推动现代农业高质量可持续发展具有重要作用。在该项目中，设计、合成了一系列含芳氧基、芳硫基和芳基氨基的乙酰肼衍生物，并通过¹ H 核磁共振 (NMR)、¹³ C NMR 和高分辨率质谱 (HRMS) 对其进行了表征。杀菌生物测定表明，一些化合物表现出优异的广谱杀菌活性，并讨论了构效关系。体内杀真菌活性表明化合物C4和D8对禾谷镰刀菌侵染小麦叶片，其中复方D8的防治活性与阳性药剂基本相当。透射电子显微镜 (TEM) 观察显示C4处理的禾谷镰刀菌中的质膜菌丝细胞严重收缩并与细胞壁分离，溶酶体可见，细胞质和细胞器消失，这可能是扫描电子显微镜（SEM）观察到菌丝干枯甚至破裂的原因。随后，进行了转录组学和代谢组学以进一步阐明杀菌机制。构建并阐述了质膜相关鞘脂代谢、亚油酸代谢、α-亚油酸代谢和花生四烯酸代谢中差异基因和代谢物的调控网络。此外，对种子生长的初步调查表明，化合物C4和D8可能对小麦幼苗的生长指标有不同程度的影响；然而，随着植物的生长，这种影响可以忽略不计。