本文研究了13个2-(N-芳基氨甲基)苯并异噻唑啉-3-酮类化合物对球等鞭金藻Isochrysis galbana、亚心形扁藻Platymonas subcordiformis及舟形藻Navicula的生长抑制性能,并测试了其对藤壶二期无节幼虫的生物活性。结果表明:2-(N-芳基氨甲基)苯并异噻唑啉-3-酮类化合物对球等鞭金藻、亚心形扁藻和舟形藻都有良好的生长抑制活性,其中对球等鞭金藻和亚心形扁藻的抑制作用较强;对藤壶幼虫的生物活性测试表明,化合物最低质量浓度为2.0 mg/L时,除化合物g和l,都具有良好的生长抑制活性。化合物的结构与浮游生物的生长抑制活性关系表现为间位取代优于对位取代。
The growing inhibitory properties on Isochrysis galbana, Platymonas subcordiformis and Navicula of thirteen 2-(N-arylaminomethyl)-3-oxo-benzo[d]isothiazoles were investigated, and the effects on biological activity of barnacle nauplii were also studied. The results indicate that the tested compounds have favourable growing inhibitory activities to the marine algas, and the better inhibitory activities are on Isochrysis galbana and Platymonas subcordiformis. The results also indicate when the lowest concentration is 2.0 mg/L, the tested compounds show a favourable growing inhibitory activity on barnacle larvae except the compound g and l. The relationship between compounds' structure and plankton growth inhibitory activity reveals that meta-substituent is better than para-substituent.
[1] HUANG Zong-guo, CAI Ru-xing. Marine fouling and its prevention[M].Volume two. Beijing:Ocean Press,2008:219-240.
黄宗国,蔡如星.海洋污损生物及其防除[M].下册.北京:海洋出版社,2008:219-240.
[2] BERNARDO A P, Da Gama, Erwan Plouguerné, et al. Chapter fourteen-The antifouling defence mechanisms of marine macroalgae[J]. Advances in Botanical Research,2014,71:413-440.
[3] PEARCE F. Offshore petroleum[M]∥Bio-fouling problems and solutions. Australia: The University of New South Wales,1994:19-31.
[4] WILSON L H, CALLOW M E. Engineered antifouling micro topographies-correlating wet-tability with cell attachment[J]. Bio-fouling,2006,22(1):11-21.
[5] REN Run-tao, LIANG Jun. Marine antifouling coatings: Development and trends[J]. Development and Application of Materials,2014,2(4):22-26.
任润桃,梁军.海洋防污涂料发展现状与研究趋势[J].材料开发与应用,2014,2(4):22-26.
[6] YU Liang-min, JIANG Xiao-hui, DONG Lei. Isothiazolinone derivatives and its application for antifouling in marine coatings[J]. Paint & Coatings Industry,2004,34(5):43-47.
于良民,姜晓辉,董磊.异噻唑啉酮类化合物及其在海洋防污涂料中的应用[J].涂料工业,2004,34(5):43-47.
[7] XU Feng-ling , LIN Qiang , YUAN Wen ,et al. Synthesis of novel benzisothiazolone derivatives as potential antifoulants[J]. Synth Commun,2006,36(5):19-21.
[8] WANG Xiang-hui, YANG Jian-xin, YOU Cheng-hang, et al. Synthesis and biological activity of benzisothiazoleones[J]. Chemical Research and Application,2011,23(10):1 290-1 294.
王向辉,杨建新,游诚航,等.苯并异噻唑啉酮类化合物的合成与活性研究[J].化学研究与应用,2011,23(10):1 290-1 294.
[9] WANG Xiang-hui, YIN Xue-qiong, FENG Wen, et al. Synthesis and antibacterial and fungicidal activity of 3-oxo-N-arylbenzo[d]isothiazole-2( 3H) -carboxamides[J]. Chinese Journal of Pesticide Science,2012,14(2):225-228.
王向辉,尹学琼,冯文,等.N-取代苯基-2-(苯并异噻唑啉-3-酮-2-基)甲酰胺的合成及抑菌活性[J].农药学学报,2012,14(2):225-228.
[10] YANG Jian-xin, YOU Cheng-hang ,WANG Xiang-hui, et al. The synthesis and bioactivities of 2-hydroxyethyl benzoisothiazole-3(2H)-one marine antifouling paints[J]. Adv Mater Res,2013,646(9):24-29.
[11] WANG Xiang-hui. Design, synthesis and biological activity of benzisothiazoleones[D]. Kunming: Kunming University of Science And Technology,2012.
王向辉.苯并异噻唑啉酮类化合物的设计、合成及生物活性研究[D].昆明:昆明理工大学,2012.
[12] ZHENG Hong-hui, WANG Xiang-hui, YANG Jian-xin, et al. Synthesis and biological activity of benzisothiazole porphyrin ketones[J]. Journal of Biology,2011,28(4):7-9.
郑洪辉,王向辉,杨建新,等.苯并异噻唑啉酮类化合物的生物活性研究[J].生物学杂志,2011,28(4):7-9.
[13] WEI Jie, WANG Xu-yu, YANG Jian-xin, et al. Synthesis and antifouling properties of 3-oxobenzo[d]isothiazole-2(3H)-phenyl formic esters[J]. Paint & Coatings Industry,2014,44(9):14-18.
魏婕,王旭裕,杨建新,等.1,2-苯并异噻唑啉-3-酮-2-甲酸苯酯类化合物的合成及防污性能研究[J].涂料工业,2014,44(9):14-18.
[14] WEI Jie, WANG Xu-yu, YANG Jian-xin, et al. Marine antifouling properties of benzo[d]isothiazole-2(3H)-carboxamides[J]. Natural Science Journal of Hainan University,2014,32(2):129-133.
魏婕,王旭裕,杨建新,等.苯并异噻唑啉酮甲酸酯类衍生物的海洋防污性能研究[J].海南大学学报:自然科学版,2014,32(2):129-133.
[15] ZHOU Yong-xin, ZHANG Zong-she. Biological aquatic toxicity testing methods[M]. First Edition. Beijing: Agriculture Press,1989:109-143,157-165.
周永欣,章宗涉.水生生物毒性试验方法[M].第一版.北京:农业出版社,1989:109-143,157-165.
[16] LI Cui-ping, WU Min-yao, WANG Hong-yuan. LC50 caculated by kochi, probit analysis and linear Regression methods[J]. Progress in Veterinary Medicine,2012,33(9):89-92.
李翠萍,吴民耀,王宏元.3种半数致死浓度计算方法之比较[J].动物医学进展,2012,33(9):89-92.
[17] GU Bing, ZHANG Zheng, LI Yu-ping,et al. Summary of median lethal dose and its calculationmethods[J]. China Occupational Medicine,2009,36(6):506-511.
顾兵,张政,李玉萍,等.半数致死剂量及其计算方法概述[J].中国职业医学,2009,36(6):506-511.
