喹啉腙类及酰腙类衍生物的合成及杀松材线虫活性评价
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摘要
[目的]开发新型的具有喹啉骨架的杀松材线虫农药。[方法]根据亚结构活性拼接原理在喹啉结构中引入-NHN=CH-结构,合成24个喹啉腙类和酰腙类衍生物,然后采用浸渍法分别测定了喹啉腙类衍生物对松材线虫的毒杀活性。[结果]目标化合物都经过熔点、IR、1H NMR、13C NMR和HRMS确定。活性研究结果表明:喹啉腙类及酰腙类衍生物具有了较好的杀松材线虫活性,LC_(50)值最低能达到4.30 mg/L。构效关系表明腙类衍生物的杀松材线虫活性比酰腙类衍生物的活性好。[结论]喹啉腙类及酰腙类衍生物对松材线虫具有较好的毒杀活性,为喹啉类衍生物在松材线虫病害防治研究奠定了一定的研究基础。
[Aims] To discover quinoline derivatives with high nematicidal activity against the pine wood nematode,Bursaphelenchus xylophilus. [Methods] Twenty-four hydrazone and acylhydrazone derivatives base on quinoline were synthesized by combining the moiety of-NHN=CH-, and investigated their nematicidal activity by using the impregnation method. [Results] All the synthesized compounds have been were characterized by m.p., IR, ~1H NMR,~(13)C NMR and HRMS. The evaluated result of these derivatives' nematicidal activities displayed that the hydrazone and acylhydrazone derivatives revealed the significant promising nematicidal activity against B. xylophilus with the best LC_(50) values of 4.30 mg/L. The preliminary structure-activity relationships indicated that hydrazone derivatives of quinoline had more nematicidal activity than acyldrazone derivatives. [Conculsions] Hydrazone and acylhydrazone derivatives base on quinoline revealed the significant promising nematicidal activity against B. xylophilus, and laid a certain foundation for the research of quinoline derivatives in the prevention and control of pine nematodes.
[Aims] To discover quinoline derivatives with high nematicidal activity against the pine wood nematode,Bursaphelenchus xylophilus. [Methods] Twenty-four hydrazone and acylhydrazone derivatives base on quinoline were synthesized by combining the moiety of-NHN=CH-, and investigated their nematicidal activity by using the impregnation method. [Results] All the synthesized compounds have been were characterized by m.p., IR, ~1H NMR,~(13)C NMR and HRMS. The evaluated result of these derivatives' nematicidal activities displayed that the hydrazone and acylhydrazone derivatives revealed the significant promising nematicidal activity against B. xylophilus with the best LC_(50) values of 4.30 mg/L. The preliminary structure-activity relationships indicated that hydrazone derivatives of quinoline had more nematicidal activity than acyldrazone derivatives. [Conculsions] Hydrazone and acylhydrazone derivatives base on quinoline revealed the significant promising nematicidal activity against B. xylophilus, and laid a certain foundation for the research of quinoline derivatives in the prevention and control of pine nematodes.
引文
[1]理永霞,张星耀.松材线虫病致病机理研究进展[J].环境昆虫学报,2018,40(2):231-241.
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[4]郑忠辉,杜德平,刘浚,等.喹啉酮结构整合酶抑制剂的设计、合成及其抗HIV-1活性研究[J].中国药物化学杂志,2015,127(5):333-338.
[5]杜鼎,方建新.具有生物活性的喹啉类化合物的最新进展[J].有机化学,2007,27(11):1318-1336.
[6]WANG Yi,YU Xiang,ZHI Xiao-yan,et al.Synthesis and Insecticidal Activity of Novel Hydrazone Compounds Derived from a Naturally Occurring Lignan Podophyllotoxin against Mythimna separata(Walker)[J].Bioorganic&Medicinal Chemistry Letters,2014,24:2621-2624.
[7]CHE Zhi-ping,ZHANG Shao-yong,SHAO Yong-hua,et al.Synthesis and Quantitative Structure-Activity Relationship(QSAR)Study of Novel N-Arylsulfonyl-3-acylindole Arylcarbonyl Hydrazone Derivatives as Nematicidal Agents[J].Journal of Agricultural and Food Chemistry,2013,61:5696-5705.
[8]GUO Yong,YAN Yuan,YANG Chun,et al.Regioselective Synthesis of Fraxinellone-based Hydrazone Derivatives as Insecticidal Agents[J].Bioorganic&Medicinal Chemistry Letters,2012,22:5384-5387.
[9]YU Xiang,FENG Gang,HUANG Jiu-lin,et al.Evaluation of Some Quinoline-based Hydrazone Derivatives as Insecticidal Agents[J].RSC Advances,2016,6:30405-30411.
[10]焦宏伟,张璐,赵宝华,等.36种中草药提取物杀松材线虫活性研究[J].中国生物防治学报,2014,30(2):239-246.
[2]LESCOAT G,L′EONCE S,PIERR′E A,et al.Antiproliferative and Iron Chelating Efficiency of the New Bis-8-Hydroxyquinoline Benzylamine Chelator S1 in Hepatocyte Cultures[J].Chem Biol Interact,2012,195(2):165-172.
[3]SEVGI F,BEDUK A D.Synthesis and Antimicrobial Activity of Novel Glyoximes Containing Quinoline Moiety[J].World Applied Sciences Journal,2012,19(2):192-197.
[4]郑忠辉,杜德平,刘浚,等.喹啉酮结构整合酶抑制剂的设计、合成及其抗HIV-1活性研究[J].中国药物化学杂志,2015,127(5):333-338.
[5]杜鼎,方建新.具有生物活性的喹啉类化合物的最新进展[J].有机化学,2007,27(11):1318-1336.
[6]WANG Yi,YU Xiang,ZHI Xiao-yan,et al.Synthesis and Insecticidal Activity of Novel Hydrazone Compounds Derived from a Naturally Occurring Lignan Podophyllotoxin against Mythimna separata(Walker)[J].Bioorganic&Medicinal Chemistry Letters,2014,24:2621-2624.
[7]CHE Zhi-ping,ZHANG Shao-yong,SHAO Yong-hua,et al.Synthesis and Quantitative Structure-Activity Relationship(QSAR)Study of Novel N-Arylsulfonyl-3-acylindole Arylcarbonyl Hydrazone Derivatives as Nematicidal Agents[J].Journal of Agricultural and Food Chemistry,2013,61:5696-5705.
[8]GUO Yong,YAN Yuan,YANG Chun,et al.Regioselective Synthesis of Fraxinellone-based Hydrazone Derivatives as Insecticidal Agents[J].Bioorganic&Medicinal Chemistry Letters,2012,22:5384-5387.
[9]YU Xiang,FENG Gang,HUANG Jiu-lin,et al.Evaluation of Some Quinoline-based Hydrazone Derivatives as Insecticidal Agents[J].RSC Advances,2016,6:30405-30411.
[10]焦宏伟,张璐,赵宝华,等.36种中草药提取物杀松材线虫活性研究[J].中国生物防治学报,2014,30(2):239-246.