Li Luwei, Chen Guangyou, Gu Huiping, Lei Peng, Gao Yanqing, Ma Zhiqing, Feng Juntao
College of Plant Protection, Northwest A&F University, 712100, Yangling, Shaanxi, China.
Shaanxi Research Center of Biopesticide Engineering & Technology, Northwest A&F University, 712100, Yangling, Shaanxi, China.
Chem Biodivers. 2024 Dec;21(12):e202401955. doi: 10.1002/cbdv.202401955. Epub 2024 Oct 28.
In order to develop novel, efficient and green fungicides, a series of novel isoaurone derivatives were designed and synthesized, which were characterized by H and C NMR, high-resolution mass spectra and melting points. The target compounds showed different inhibitory activities against seven plant pathogenic fungi. Compounds 1, 12, 17, 20, 22, 24 and intermediate A showed more than 90 % inhibition rates against S. s at 50 mg/L. Interestingly, compound 22 and intermediate A showed the great inhibitory effect against S. s with EC values of 4.65 and 4.24 mg/L, which were better than the lead compound isoaurone (EC=15.62 mg/L). The EC values of compounds 17 and 24 against B. c were 13.94 and 22.13 mg/L. Moreover, compound 19 displayed significant antifungal activity against G. g with the EC value of 11.88 mg/L. Theoretical calculations by DFT revealed that the α, β-unsaturated carbonyl bond and the benzyl ring are very importantly linked to the strength of the fungicidal activity. Therefore, this study identified a valuable antifungal lead compound for further development of green fungicides.
为了开发新型、高效且绿色的杀菌剂，设计并合成了一系列新型异奥酮衍生物，通过氢核磁共振（H NMR）、碳核磁共振（C NMR）、高分辨质谱和熔点对其进行了表征。目标化合物对七种植物病原真菌表现出不同的抑制活性。化合物1、12、17、20、22、24和中间体A在50 mg/L时对核盘菌（S. s）的抑制率超过90%。有趣的是，化合物22和中间体A对核盘菌表现出很强的抑制作用，其半数有效浓度（EC）值分别为4.65和4.24 mg/L，优于先导化合物异奥酮（EC = 15.62 mg/L）。化合物17和24对灰葡萄孢（B. c）的EC值分别为13.94和22.13 mg/L。此外，化合物19对香蕉炭疽病菌（G. g）表现出显著的抗真菌活性，EC值为11.88 mg/L。密度泛函理论（DFT）的理论计算表明，α,β-不饱和羰基键和苄基环与杀菌活性的强度密切相关。因此，本研究确定了一种有价值的抗真菌先导化合物，可用于进一步开发绿色杀菌剂。
