8-氯-6-(三氟甲基)咪唑并1,2-a吡啶噻二唑、三唑衍生物的设计、合成及其杀线虫、杀菌活性

    Design, synthesis, and nematicidal and fungicidal activity of 8-chloro-6-(trifluoromethyl) imidazo 1,2-a pyridine thiadiazole/triazole derivatives

    • 摘要: 为发现具有高活性的新型杀线虫和杀菌化合物,本研究以2-氨基-3-氯-5-三氟甲基吡啶为原料,利用活性亚结构拼接原理,将1,3,4-噻二唑、1,2,4-三唑等结构引入咪唑并1,2-a吡啶,设计并合成了24个未见报道的8-氯-6-(三氟甲基)咪唑并1,2-a吡啶噻二唑、三唑衍生物,其结构均经过核磁共振氢谱(1H NMR)、碳谱(13C NMR)和高分辨质谱(HRMS)确证。杀线虫结果显示,质量浓度为100 mg/L时,所有化合物对秀丽隐杆线虫均表现出不同程度的毒力,其中化合物9e9f9i9k10d10h在48 h后的校正死亡率分别为94.10%、84.08%、93.74%、91.82%、92.61%和88.90%,优于对照药剂噻唑膦(60.28%),但低于氟吡菌酰胺(100%),但对松材线虫的毒力不理想,只有化合物9c9l有中等的杀线虫活性,校正死亡率分别为50.27%和49.43%,低于对照药剂噻唑膦(52.04%)和氟吡菌酰胺(96.50%)。菌丝生长速率法测定的室内杀菌活性结果显示,化合物9a9c对水稻纹枯病菌(Rhizoctonia solani)的EC50值分别为57.35和34.75 mg/L,其活性优于对照药剂氟吡菌酰胺(122.37 mg/L),但低于多菌灵(0.48 mg/L)。本研究合成的咪唑并1,2-a吡啶噻二唑/三唑类化合物具有一定的杀线虫和杀菌活性,为咪唑并1,2-a吡啶类化合物的进一步研发提供了参考。

       

      Abstract: To discover new nematicidal and fungicidal compounds with high activity, 1,3,4-thiadiazole and 1,2,4-triazole structures were introduced into imidazo 1,2-a pyridine by using the principle of active substructure splice, with 2-amino-3-chloro-5-trifluoromethyl pyridine as raw material. Twenty-four unreported 8-chloro-6-(trifluoromethyl) imidazo 1,2-a pyridine thiadiazole/triazole derivatives were designed and synthesized, and their structures were confirmed by 1H NMR, 13C NMR and HRMS. The results indicated that all the compounds showed different levels of toxic activity against Caenorhabditis elegans when the concentration was 100 mg/L. After 48 h, the corrected mortality rates of compounds 9e, 9f, 9i, 9k, 10d and 10h were 94.10%, 84.08%, 93.74%, 91.82%, 92.61% and 88.90%, respectively, which were better than the control agent fosthiazate (60.28%), but lower than fluopyram (100%). The toxicity of the target compound to Bursaphelenchus xylophilus was not ideal. At a concentration of 100 mg/L, only compounds 9c and 9l exhibited moderate nematicidal activity, with corrected mortality rates of 50.27% and 49.43%, respectively, which were lower than the control agents fosthiazate (52.04%) and fluopyram (96.50%). The results of the fungicidal activity assay by mycelium growth rate method showed that EC50 values of compounds 9a and 9c were 57.35 and 34.75 mg/L, respectively, which were better than the control agent fluopyram (122.37 mg/L), but lower than carbendazim (0.48 mg/L). The imidazo 1,2-a pyridine thiadiazole/triazole compounds synthesized in this study have certain nematoidal and fungicidal activities, and provide a reference for further exploration of imidazo 1,2-a pyridine compounds.

       

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