Department of Applied Chemistry, School of Science, Anhui Agricultural University, Hefei, China.
Department of Pesticide Science, College of Plant Protection, Northwest A&F University, Yangling, China.
Pest Manag Sci. 2021 Jul;77(7):3529-3537. doi: 10.1002/ps.6406. Epub 2021 May 12.
To promote the discovery and development of new fungicide with novel scaffolds or modes of action, a series of novel 5-(2-chloroethyl)-1-phenyl-6-(pyridin-4-yl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one derivatives were synthesized, and evaluated for their antifungal activities.
The bioassay data showed that compound 8IIId (EC = 1.93 mg L ) is superior to boscalid (EC = 6.71 mg L ) against Valsa mali. We introduced chiral groups on the structure of 8IIId, and two chiral configurations were respectively synthesized, which are 8Vc and 8Vd. Surprisingly, 8Vc showed significant antifungal activities against Valsa mali and Physalospora piricola with EC values of 0.22 and 0.55 mg L . Physiological and biochemical studies showed that the primary action mechanism of compound 8Vc on Valsa mali may involve changing mycelial morphology and increasing cell membrane permeability.
These results demonstrated that 8Vc could be further modified as fungicide and provided a valuable reference for antifungal agents with pyrazolo[3,4-d]pyrimidin-4-one skeleton. © 2021 Society of Chemical Industry.
为了发现和开发具有新型骨架或作用模式的新型杀菌剂，我们合成了一系列新型 5-(2-氯乙基)-1-苯基-6-(吡啶-4-基)-1,5-二氢-4H-吡唑并[3,4-d]嘧啶-4-酮衍生物，并对其进行了抗真菌活性评估。
生物测定数据表明，化合物 8IIId（EC = 1.93 毫克/升）对苹果腐烂病菌的活性优于肟菌酯（EC = 6.71 毫克/升）。我们在 8IIId 的结构中引入了手性基团，分别合成了两种手性构型，即 8Vc 和 8Vd。令人惊讶的是，8Vc 对苹果腐烂病菌和梨黑星病菌表现出显著的抗真菌活性，EC 值分别为 0.22 和 0.55 毫克/升。生理生化研究表明，化合物 8Vc 对苹果腐烂病菌的主要作用机制可能涉及改变菌丝形态和增加细胞膜通透性。
这些结果表明，8Vc 可以进一步修饰为杀菌剂，为具有吡唑并[3,4-d]嘧啶-4-酮骨架的抗真菌剂提供了有价值的参考。 © 2021 化学工业协会。
