State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, China.
State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agricultural Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, China.
Pestic Biochem Physiol. 2021 Jun;175:104857. doi: 10.1016/j.pestbp.2021.104857. Epub 2021 Apr 16.
To discover new nematicides, a series of novel amide derivatives containing an imidazo[1,2-a]pyridine moeity were designed and synthesized. Among the title compounds, compounds 3 and 27 exhibited good nematicidal activities against Aphelenchoides besseyi (rice white-tip nematode), with LC values against of 27.3 and 35.9 mg/L, respectively, which were superior to that of fosthiazate (45.4 mg/L). Meanwhile, the LC value of compound 27 against Caenorhabditis elegans was 5.7 mg/L, which was superior to that of fosthiazate (77.2 mg/L). Compound 27 not only binds well to acetylcholinesterase (AChE) of nematodes, but also has a good inhibitory activity against AChE. Thus, AChE may be a potential target of compound 27 against nematodes. Unexpectedly, compound 28 exhibited excellent antibacterial activities with EC values of 1.2 and 3.1 mg/L against Xanthomonas oryzae pv. oryzae (Xoo) and Xanthomonas oryzae pv. oryzicola (Xoc), respectively, which were superior to those of bismerthiazol (68.6 and 77.1 mg/L) and thiodiazole copper (80.8 and 96.6 mg/L). The curative and protective activities of compound 28 against bacterial leaf blight were 37.0% and 36.8% at 50 mg/L, respectively, which were higher than those of thiodiazole copper (16.1% and 15.5%). In addition, compound 28 may inhibit the growth of Xoo by affecting the production of cell membranes and extracellular polysaccharides. Amide derivatives containing an imidazo[1,2-a]pyridine moeity can be used as good lead-structures to discover new nematicidal and antibacterial agents in the future.
为了发现新的杀线虫剂，设计并合成了一系列含有咪唑并[1,2-a]吡啶结构单元的新型酰胺衍生物。在标题化合物中，化合物 3 和 27 对 Aphelenchoides besseyi（水稻白尖线虫）表现出良好的杀线虫活性，LC 值分别为 27.3 和 35.9mg/L，优于福噻唑（45.4mg/L）。同时，化合物 27 对秀丽隐杆线虫的 LC 值为 5.7mg/L，优于福噻唑（77.2mg/L）。化合物 27 不仅与线虫乙酰胆碱酯酶（AChE）结合良好，而且对 AChE 具有良好的抑制活性。因此，AChE 可能是化合物 27 对线虫的潜在靶标。出乎意料的是，化合物 28 对 Xanthomonas oryzae pv. oryzae（Xoo）和 Xanthomonas oryzae pv. oryzicola（Xoc）具有优异的抗菌活性，EC 值分别为 1.2 和 3.1mg/L，优于双噻唑铜（68.6 和 77.1mg/L）和噻二唑铜（80.8 和 96.6mg/L）。化合物 28 对细菌性条斑病的防治效果分别为 50mg/L 时的 37.0%和 36.8%，高于噻二唑铜（16.1%和 15.5%）。此外，化合物 28 可能通过影响细胞膜和胞外多糖的产生来抑制 Xoo 的生长。含有咪唑并[1,2-a]吡啶结构单元的酰胺衍生物可作为未来发现新的杀线虫和抗菌剂的良好先导结构。
