苯酰胺类化合物防污活性基团的初步探索

Preliminary study of the antifouling active groups of benzamide compounds

开发绿色环保防污剂是海洋船舶防污涂料研究的重要方向,查明防污活性化合物分子结构中的防污活性基团,是设计开发新型防污剂的关键。本文合成了3种结构相似的苯酰胺类化合物HNOB、DOLPA和DHNOB,通过FTIR,^(1)H NMR,^(13)C NMR测试表征3种化合物的分子结构,利用典型污损生物硅藻和贻贝作为目标生物,测试其对硅藻和贻贝附着的影响,并将分子结构与防污活性进行对比,初步探讨影响防污性能的活性基团。硅藻和贻贝附着实验均表明,HNOB的防污性能较好,半数抑制浓度远低于DOLPA和DHNOB。通过结构对比分析发现,极性和非极性结构的协同作用比单一的极性基团或非极性长碳链基团能更好地赋予苯酰胺类物质良好的防污性能。该研究初步探讨了苯酰胺类化合物的构效关系,有助于新型防污活性化合物的设计开发和结构优化,并对探究该类化合物防除污损生物附着的机理和快速筛选有潜力的防污化合物具有重要意义。

The development of green antifoulants is an important research direction for marine antifouling coatings,and the identification of antifouling active groups in the molecular structure of active compounds is crucial in designing and developing new antifoulants.In this study,three benzamide compounds,namely,HNOB,DOLPA,and DHNOB with similar structures,were synthesized,and their molecular structures were characterized via FTIR,^(1)H NMR,and ^(13)C NMR analysis techniques.The effects of these compounds on the adhesion of diatoms and mussels were tested.Next,their molecular structures and antifouling activities were compared,and the active groups affecting the antifouling performance were discussed.The adhesion experiments of diatoms and mussels demonstrated that HNOB exhibited better antifouling performance,and its half inhibitory concentration was considerably lower than those of DOLPA and DHNOB.The synergistic effect of polar and nonpolar structures was observed to be better than that of the single polar group or nonpolar long carbon chain group in endowing benzamide with good antifouling performance.This study explores the conformational relationships of benzamide analogs,which can help the design and development of new antifoulants and structural optimization and is important for the rapid screening of promising antifoulants.