Synthesis, Structural Characterization, and Antibacterial and Antifungal Activities of Novel 1,2,4-Triazole Thioether and Thiazolo[3,2-b]-1,2,4-triazole Derivatives Bearing the 6-Fluoroquinazolinyl Moiety

稻黄单胞菌 抗菌剂 部分 三唑 化学 EC50型 索拉尼链格孢菌 立体化学 生物化学 生物 杀菌剂 体外 有机化学 植物 基因
作者
Muhan Ding,Suran Wan,Nan Wu,Yan Ye,Junhong Li,Xiaoping Bao
出处
期刊:Journal of Agricultural and Food Chemistry [American Chemical Society]
卷期号:69 (50): 15084-15096 被引量:15
标识
DOI:10.1021/acs.jafc.1c02144
摘要

A total of 52 novel 1,2,4-triazole thioether and thiazolo[3,2-b]-1,2,4-triazole derivatives bearing the 6-fluoroquinazolinyl moiety were designed, synthesized, and evaluated as antimicrobial agents in agriculture based on the molecular hybridization strategy. Among them, molecular structures of compounds 5g and 6m were further confirmed via the single-crystal X-ray diffraction method. The bioassay results indicated that some of the target compounds possessed excellent antibacterial activities in vitro against the pathogen Xanthomonas oryzae pv. oryzae (Xoo). For example, compound 6u demonstrated a strong anti-Xoo efficacy with an EC50 value of 18.8 μg/mL, nearly 5-fold more active than that of the commercialized bismerthiazol (EC50 = 93.6 μg/mL). Moreover, the anti-Xoo mechanistic studies revealed that compound 6u exerted its antibacterial effects by increasing the permeability of bacterial membrane, reducing the content of extracellular polysaccharide, and inducing morphological changes of bacterial cells. Importantly, in vivo assays revealed its pronounced protection and curative effects against rice bacterial blight, proving its potential as a promising bactericide candidate for controlling Xoo. Moreover, compound 6u had a good pesticide-likeness based on Tice's criteria. More interestingly, compound 6u with high anti-Xoo activity also demonstrated a potent inhibitory effect of 80.8% against the fungus Rhizoctonia solani at 50 μg/mL, comparable to that of the commercialized chlorothalonil (85.9%). Overall, the current study will provide useful guidance for the rational design of more efficient agricultural antimicrobial agents using the thiazolo[3,2-b]-1,2,4-triazole derivatives bearing the 6-fluoroquinazolinyl moiety as lead compounds.
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