Abstract：
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.
CONCLUSIONS: This study provides a basis for exploiting potential rosin-based fungicides in promoting sustainable crop protection. © 2022 Society of Chemical Industry.
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.
CONCLUSIONS: This study provides a basis for exploiting potential rosin-based fungicides in promoting sustainable crop protection. © 2022 Society of Chemical Industry.
摘要：
背景：使用杀菌剂保护农作物免受疾病侵害是一种有效的方法，和具有增强性能和低毒性的新型环保植物源杀菌剂是可持续农业的迫切需求。
结果：设计并制备了两种松香基酰腙类化合物。基于对枯萎病菌的抗真菌活性评估，尖孢镰刀菌,辣椒疫霉,菌核病,和灰葡萄孢菌,筛选了含有噻吩环的酰腙衍生物，并对水稻R.solani具有抑制作用。其中,化合物4n,苯环结构上的吸电子基团与噻吩环相连，显示出最佳的活性，EC50值为0.981mgL-1，低于多菌灵。此外，表明4n可以影响菌丝形态，细胞膜通透性和微观结构，在真菌细胞中产生活性氧，损伤细胞核和线粒体的生理功能,导致R.solani细胞死亡.同时,化合物4n对体内水稻植物表现出更好的治疗效果。然而,4n对水稻叶鞘中防御酶的诱导活性表明，4n通过去除活性氧刺激水稻植株的初始抗性，从而保护细胞膜或增强细胞壁的强度。通过定量构效关系研究,定量化学和静电描述符显着影响4n与受体的结合，提高了其抗真菌活性。
结论：本研究为开发潜在的松香基杀菌剂促进可持续作物保护提供了基础。©2022化学工业学会。
结果：设计并制备了两种松香基酰腙类化合物。基于对枯萎病菌的抗真菌活性评估，尖孢镰刀菌,辣椒疫霉,菌核病,和灰葡萄孢菌,筛选了含有噻吩环的酰腙衍生物，并对水稻R.solani具有抑制作用。其中,化合物4n,苯环结构上的吸电子基团与噻吩环相连，显示出最佳的活性，EC50值为0.981mgL-1，低于多菌灵。此外，表明4n可以影响菌丝形态，细胞膜通透性和微观结构，在真菌细胞中产生活性氧，损伤细胞核和线粒体的生理功能,导致R.solani细胞死亡.同时,化合物4n对体内水稻植物表现出更好的治疗效果。然而,4n对水稻叶鞘中防御酶的诱导活性表明，4n通过去除活性氧刺激水稻植株的初始抗性，从而保护细胞膜或增强细胞壁的强度。通过定量构效关系研究,定量化学和静电描述符显着影响4n与受体的结合，提高了其抗真菌活性。
结论：本研究为开发潜在的松香基杀菌剂促进可持续作物保护提供了基础。©2022化学工业学会。
