Pest disasters which occurs on crops is a serious problem that not only cause crop yield loss or even crop failure but can also spread a number of plant diseases.Sulfonate derivatives have been widely used in insecticide and fungicide research in recent years. On this basis, a series of sulfonate derivatives bearing an amide unit are synthesized and the biological activities are evaluated. The bioassay results showed that compounds A8, A13, A16, B1, B3, B4, B5, B10, B12 − 20, C3, C5, C9, C10, C14, C15, C17 and C19 showed 100% activity at a concentration of 500 µg/mL against the Plutella xylostella (P. xylostella). Among them, B15 which contains a thiadiazole sulfonate structure still shows 100% activity at 50 µg/mL concentration against P. xylostella and had the lowest median lethal concentration (LC50) (7.61 µg/mL) among the target compounds. Further mechanism studies are conducted on compounds with better insecticidal activity. Molecular docking results shows that B15 formed hydrophobic interactions π-π and hydrogen bonds with the indole ring of Trp532 and the carboxyl group of Asp384, respectively, with similar interaction distances or bond lengths as those of diflubenzuron. Moreover, chitinase inhibition assays are performed to further demonstrate its mode of action. In addition, the anti-bacterial activity of the series of compounds is also tested and the results showed that the series of compounds has moderate biological activity against Xanthomonas oryzae pv. oryzae (Xoo) and Xanthomonas oryzae pv. oryzicola (Xoc), with inhibition rates of 91%, 92% and 92%, 88% at the concentration of 100 µg/mL, respectively. Our study indicates that B15 can be used as a novel insecticide for crop protection.

中文翻译：

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带有酰胺单元的磺酸盐衍生物：设计、合成和生物活性研究

农作物发生的病虫害是一个严重的问题，不仅会导致农作物减产甚至绝收，还会传播多种植物病害。近年来，磺酸盐衍生物在杀虫剂和杀菌剂的研究中得到了广泛的应用。在此基础上，合成了一系列带有酰胺单元的磺酸盐衍生物，并对其生物活性进行了评价。生物测定结果表明，化合物A8、A13、A16、B1、B3、B4、B5、B10、B12-20、C3、C5、C9、C10、C14、C15、C17和C19在500浓度下表现出100%的活性。 µg/mL 针对小菜蛾 (P. xylostella)。其中，含有噻二唑磺酸盐结构的B15在50 µg/mL浓度下对小菜蛾仍显示出100%的活性，并且在目标化合物中具有最低的半数致死浓度（LC50）（7.61 µg/mL）。对具有更好杀虫活性的化合物进行了进一步的机理研究。分子对接结果表明，B15分别与Trp532的吲哚环和Asp384的羧基形成疏水相互作用π-π和氢键，相互作用距离或键长与除虫脲相似。此外，进行几丁质酶抑制测定以进一步证明其作用模式。此外，还对该系列化合物的抗菌活性进行了测试，结果表明该系列化合物对米黄单胞菌具有中等的生物活性。米霉 (Xoo) 和米黄单胞菌 pv. oryzicola (Xoc)，浓度为 100 µg/mL 时抑制率分别为 91%、92% 和 92%、88%。我们的研究表明B15可以作为一种新型杀虫剂用于作物保护。