College of Materials and Chemistry and School of Plant Protection, Anhui Agricultural University, Hefei 230036, China.
Joint Research Center for Food Nutrition and Health of IHM, Hefei 230051, China.
J Agric Food Chem. 2024 Oct 9;72(40):22045-22053. doi: 10.1021/acs.jafc.4c05050. Epub 2024 Sep 25.
To develop further novel environmentally friendly antifungal agents with high efficacy, a series of pyrazole-5-sulfonamide derivatives were designed and synthesized by using the active molecules synthesized in previous works as lead compounds. Their antifungal activities were evaluated in vitro against ten highly destructive plant pathogenic fungi. The bioassay results indicated that more than half of the target compounds displayed potent antifungal activities (inhibition rate ≥85%) against and at 20 mg/L. Among them, compound exhibited significant broad-spectrum antifungal activities against , , , , and , with EC values of 0.45, 0.49, 3.06, 0.57, and 1.43 mg/L, respectively. Moreover, compounds and exhibited remarkable protective effects on apple canker similar to (89.5%) at 50 mg/L. Preliminary antifungal mechanism investigations demonstrated that compound may have inhibited mycelial growth by inducing oxidative damage to the mycelium and compromising the integrity of the cell membrane. Meanwhile, compounds and exhibited no obvious toxicity to worker bees ( ligustica). Taken together, these pyrazole-5-sulfonamide derivatives, particularly compound , possess huge potential to be developed as novel environmentally friendly fungicides with high efficacy.
为了开发进一步具有高效、环保的新型抗真菌剂，本研究以前期工作中合成的活性分子为先导化合物，设计并合成了一系列吡唑-5-磺酰胺衍生物。采用菌丝生长速率法，在 20 mg/L 浓度下，对这一系列化合物进行了抗十种重要植物病原真菌的活性评价。生物测定结果表明，半数以上的目标化合物对 和 具有较强的抑制活性（抑制率≥85%）。其中，化合物 对 、 、 、 、 和 显示出广谱抗真菌活性，EC 值分别为 0.45、0.49、3.06、0.57 和 1.43 mg/L。此外，化合物 和 在 50 mg/L 浓度下对苹果腐烂病的保护效果与 （89.5%）相当。初步的抗真菌机制研究表明，化合物 可能通过诱导菌丝氧化损伤和破坏细胞膜完整性来抑制 菌丝生长。同时，化合物 和 对意大利蜜蜂（ ligustica）没有明显的毒性。综上所述，这些吡唑-5-磺酰胺衍生物，特别是化合物 ，具有作为高效、环保新型杀菌剂开发的巨大潜力。
