Tian Guang-Min, Yi Ming-Yan, Yan Tai-Sen, Liu Song-Song, Huang Jian, Li Hong, Bao Xiao-Ping
State Key Laboratory of Green Pesticide, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Centre for Research and Development of Fine Chemicals, Guizhou University, Guiyang, China.
Pest Manag Sci. 2025 Mar;81(3):1624-1637. doi: 10.1002/ps.8566. Epub 2024 Dec 4.
To find efficient agricultural fungicides, 29 new 4-thioquinazoline-containing acetohydrazide derivatives were prepared and tested for their fungicidal properties.
All of the target compounds were characterized by H and C nuclear magnetic resonance and high-resolution mass spectrometry techniques, and the molecular structure of compound A2 was verified by single-crystal X-ray diffraction measurement. The experimental results revealed that many compounds from this series had impressive inhibition efficacies in vitro against the tested fungi. For example, compound A25 was identified as the best fungicidal agent against Rhizoctonia solani with an EC (half-maximal effective concentration) value of 0.66 μg mL, superior to those of the commercial fungicides chlorothalonil, carbendazim and boscalid. Additionally, this compound displayed favorable protection and curative activities in vivo against rice sheath blight caused by R. solani. Antifungal mechanistic studies on compound A25 indicated that this compound exerted its strong anti-R. solani effects probably through an effective inhibition of fungal succinate dehydrogenase activity [half-maximal inhibitory concentration (IC) = 4.88 μm] and the impairment of cell membrane integrity, based on the results from enzymatic bioassays, molecular docking studies, and scanning and transmission electron microscopy observations.
Acetohydrazide derivatives containing the 4-thioquinazoline moiety had the potential to be employed as lead compounds for developing more efficient agricultural fungicides in the near future. © 2024 Society of Chemical Industry.
为了寻找高效的农用杀菌剂，制备了29种新型含4-硫代喹唑啉的乙酰肼衍生物，并对其杀菌性能进行了测试。
所有目标化合物均通过氢和碳核磁共振以及高分辨率质谱技术进行了表征，化合物A2的分子结构通过单晶X射线衍射测量得到了验证。实验结果表明，该系列中的许多化合物在体外对受试真菌具有令人印象深刻的抑制效果。例如，化合物A25被确定为对茄丝核菌的最佳杀菌剂，其EC（半数有效浓度）值为0.66μg/mL，优于商业杀菌剂百菌清、多菌灵和啶酰菌胺。此外，该化合物在体内对由茄丝核菌引起的水稻纹枯病表现出良好的保护和治疗活性。对化合物A25的抗真菌作用机制研究表明，基于酶促生物测定、分子对接研究以及扫描和透射电子显微镜观察结果，该化合物可能通过有效抑制真菌琥珀酸脱氢酶活性[半数抑制浓度（IC）=4.88μm]和损害细胞膜完整性来发挥其对茄丝核菌的强大抗菌作用。
含4-硫代喹唑啉部分的乙酰肼衍生物有潜力在不久的将来用作开发更高效农用杀菌剂的先导化合物。©2024化学工业协会。
