Discovery of rosin-based acylhydrazone derivatives as potential antifungal agents against rice Rhizoctonia solani for sustainable crop protection
Discovery of rosin-based acylhydrazone derivatives as potential antifungal agents against rice Rhizoctonia solani for sustainable crop protection
复制标题
发现松香基酰腙衍生物作为抗水稻立枯丝核菌的潜在抗真菌剂，实现可持续作物保护
DOI：
10.1002/ps.7232
复制
发表时间：
2022-10-29
影响因子：
4.1
通讯作者：
Li, Jian
中科院分区：
文献类型：
--
作者：
Xu, Renle;Gu, Shihao;Li, Jian
使用杀真菌剂保护作物免受病害是一种有效的方法，并且具有增强的性能和低毒性的新型环境友好的植物源杀真菌剂是可持续农业的迫切需求。结果设计并合成了两种松香酰腙类化合物。在对水稻纹枯病菌、尖孢镰刀菌、辣椒疫霉、核盘菌和灰葡萄孢的抑菌活性评价的基础上，筛选了含噻吩环的酰腙类化合物，并对水稻纹枯病菌、尖孢镰刀菌、辣椒疫霉、核盘菌和灰葡萄孢进行了抑菌活性测定。索拉尼其中，苯环结构上带有吸电子基团的化合物4 n表现出最佳的活性，其EC 50值为0.981 mg L-1，低于多菌灵。进一步研究表明，4 n可影响菌丝形态、细胞膜透性和显微结构，引起真菌细胞内活性氧的产生，并损伤细胞核和线粒体的生理功能，导致真菌细胞死亡。索拉尼同时，化合物4 n对活体水稻植株表现出更好的治疗效果。而4 n对水稻叶鞘中防御酶的诱导活性表明，4 n通过清除活性氧，从而保护细胞膜或增强细胞壁的强度，刺激水稻植株的初始抗性。通过定量构效关系研究发现，定量化学和静电参数显著影响4 n与受体的结合，从而提高了其抗真菌活性。结论该研究为开发松香基杀菌剂促进作物可持续保护提供了依据。(c)2022化学工业协会。
BACKGROUND The use of fungicides to protect crops from diseases is an effective method, and novel environmentally friendly plant-derived fungicides with enhanced performance and low toxicity are urgent requirements for sustainable agriculture. RESULTS Two kinds of rosin-based acylhydrazone compounds were designed and prepared. Based on the antifungal activity assessment against Rhizoctonia solani, Fusarium oxysporum, Phytophthora capsici, Sclerotinia sclerotiorum, and Botrytis cinerea, acylhydrazone derivatives containing a thiophene ring were screened and showed an inhibitory effect on rice R. solani. Among them, Compound 4n, with an electron-withdrawing group on the benzene ring structure attached to the thiophene ring, showed optimal activity, and the EC50 value was 0.981 mg L-1, which was lower than that of carbendazim. Furthermore, it was indicated that 4n could affect the mycelial morphology, cell membrane permeability and microstructure, cause the generation of reactive oxygen species in fungal cells, and damage the nucleus and mitochondrial physiological function, resulting in the cell death of R. solani. Meanwhile, Compound 4n exhibited a better therapeutic effect on in vivo rice plants. However, the induction activity of 4n on the defense enzyme in rice leaf sheaths showed that 4n stimulates the initial resistance of rice plants by removing active oxygen, thereby protecting the cell membrane or enhancing the strength of the cell wall. Through the quantitative structure-activity relationship study, the quantitative chemical and electrostatic descriptors significantly affect the binding of 4n with the receptor, which improves its antifungal activity. CONCLUSION This study provides a basis for exploiting potential rosin-based fungicides in promoting sustainable crop protection. (c) 2022 Society of Chemical Industry.