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Combination of 1,4-naphthoquinone with benzothiazoles had selective algicidal effects against harmful algae

机译:1,4-萘醌与苯并噻唑类化合物对有害藻类具有选择性杀藻作用

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摘要

A series of naphthoquinone-benzothiazole conjugates were synthesized as algicides, and their efficacies against harmful algal blooming species, such as Chattonella marina, Heterosigma akashiwo and Cochlodinium polykrikoides, were examined. The introduction of substituted benzothiazole at the C2 position of 1,4-naphthoquinone (compounds 1–9) resulted in higher algicidal activity against C. polykrikoides than the C6 conjugates (compounds 10–20). On the other hand, of the C6 conjugates, compounds 11 and 12 exhibited better algicidal activity against H. akashiwo, C. marina, and C. polykrikoides than the C2 conjugates. Further structure-activity analysis indicated that a replacement of the methoxy groups with hydroxyl groups (compounds 21–26) decreased the algicidal activity significantly. Among the various synthetic naphthoquinonebezothiazole conjugates tested, compound 12 was found to affect the most significant decrease in the level of C. polykrikoides growth, with an IC50 of 0.19 μM. Compound 11 was found to be the most potent inhibitor against H. akashiwo and C. polykrikoides, with IC50 values of 0.32 and 0.12 μM, respectively. Overall, these results highlight a possible method for controlling and inhibiting red tide forming algae using NQ derivatives.
机译:合成了一系列萘醌-苯并噻唑缀合物作为杀藻剂,并研究了它们对有害藻类开花物种(如滨海Chattonella marina,Heterosigma akashiwo和Cochlodinium polykrikoides)的功效。在1,4-萘醌的C2位置(化合物1–9)引入取代的苯并噻唑,比C6缀合物(化合物10–20)具有更高的抗多角衣藻的杀藻活性。另一方面,在C6缀合物中,化合物11和12显示出比C2缀合物更好的针对赤子芥,C.marina和C.polykrikoides的杀藻活性。进一步的结构活性分析表明,用羟基(化合物21-26)取代甲氧基可显着降低其杀藻活性。在测试的各种合成萘醌苯并噻唑共轭物中,发现化合物12影响多角衣藻生长水平的最显着降低,IC50为0.19μM。已发现化合物11是最有效的针对akashiwo和C. polykrikoides的抑制剂,IC50值分别为0.32和0.12μM。总体而言,这些结果突出了使用NQ衍生物控制和抑制赤潮形成藻类的可能方法。

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