A series of new 1-tert-butyl-5-amino-4-pyrazole bioxadiazole sulfide derivatives containing a 1,3,4-oxadiazole moiety were designed and synthesized. The bioactivity results showed that some title compounds exhibited excellent protective activity against TMV and certain insecticidal activity. Among the tested compounds, the EC50 values of 5d, 5j, 5k and 5l were 165.8, 163.2, 159.7 and 193.1 mg/L, respectively, which are better than the EC50 value of ningnanmycin (271.3 mg/L). The chlorophyll contents and the defense enzyme activities of the tobacco leaves after treatment with 5j were significantly increased, which indicated that this series of title compounds may induce the systemic acquired resistance of host to defend against diseases. Further in vivo protective activity research on 5j using TMV with a GFP gene tag found that it can effectively inhibit the spread of TMV in inoculated tobacco. A morphological study with TEM revealed that title compound 5h can cause a distinct break of the rod-shaped TMV. Moreover, the insecticidal activity revealed that the fatality rates of 5a, 5b and 5m against aphidoidea were 85%, 83% and 87%, respectively, which indicated that the title compounds can effectively block the common carrier of plant viruses, thereby effectively reducing the TMV infection risk of tobacco. This series of synergistic effects provide key information for the research and development of antiviral agents.

中文翻译：

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研究用含有 1,3,4-恶二唑硫化物部分的新型 1-(叔丁基)-5-氨基-4-吡唑衍生物处理的 TMV 体内抗病毒活性

设计并合成了一系列含有 1,3,4-恶二唑部分的新型 1-叔丁基-5-氨基-4-吡唑生物恶二唑硫化物衍生物。生物活性结果表明，部分标题化合物对TMV表现出优异的保护活性和一定的杀虫活性。在被测化合物中，5d、5j、5k和5l的EC50值分别为165.8、163.2、159.7和193.1 mg/L，优于宁南霉素的EC50值（271.3 mg/L）。5j处理后烟叶的叶绿素含量和防御酶活性显着增加，表明该系列标题化合物可能诱导宿主对疾病的系统性获得性抵抗。使用带有 GFP 基因标签的 TMV 对 5j 的进一步体内保护活性研究发现，它可以有效抑制 TMV 在接种烟草中的传播。使用 TEM 进行的形态学研究表明，标题化合物 5h 会导致棒状 TMV 的明显断裂。此外，杀虫活性显示5a、5b和5m对蚜虫的致死率分别为85%、83%和87%，表明标题化合物能有效阻断植物病毒的共同载体，从而有效降低烟草的 TMV 感染风险。这一系列协同效应为抗病毒药物的研发提供了关键信息。此外，杀虫活性显示5a、5b和5m对蚜虫的致死率分别为85%、83%和87%，表明标题化合物可以有效阻断植物病毒的共同载体，从而有效降低烟草的 TMV 感染风险。这一系列协同效应为抗病毒药物的研发提供了关键信息。此外，杀虫活性显示5a、5b和5m对蚜虫的致死率分别为85%、83%和87%，表明标题化合物可以有效阻断植物病毒的共同载体，从而有效降低烟草的 TMV 感染风险。这一系列协同效应为抗病毒药物的研发提供了关键信息。