新型吡唑酰胺类化合物的设计、合成与生物活性Design, synthesis and biological evalulation of novel pyrazolecarboxamides
毛明珍;张晓光;张媛媛;卫天琪;张选利;崔哲;张建功;李玉新;
摘要(Abstract):
[目的]寻找较高杀虫活性的吡唑酰胺类化合物并进行结构优化。[方法]设计合成一系列含有多种苯环2-位取代基结构的吡唑酰胺类化合物。[结果]合成了7个结构新颖的含有苯环2-位取代基结构的吡唑酰胺类化合物,其结构经过1H NMR和有机元素分析或高分辨质谱确证,并进行了杀虫活性测试研究。[结论]杀虫活性测试结果表明:部分目标化合物对小菜蛾和东方黏虫具有较好的杀虫活性,值得进一步研究。
关键词(KeyWords): 氯虫酰胺;吡唑酰胺类化合物;合成;杀虫活性
基金项目(Foundation):
作者(Authors): 毛明珍;张晓光;张媛媛;卫天琪;张选利;崔哲;张建功;李玉新;
参考文献(References):
- [1]CONCH-MEYER A,GRANDON S,SEPULVEDA G,et al.Pesticide residues quantification in frozen fruit and vegetables in chilean domestic market using QuEChERS extraction with ultra-high-performance liquid chromatography clectrospray ionization orbitrap mass spectrometry[J].Food Chem,2019,295:64-71.
- [2]LAHM G P,CORDOVA D,BARRY J D,et al.New and selective ryanodine receptor activators for insect control[J].Bioorg Med Chem,2009,17:4127-4133.
- [3]ZHOU Yuan-yuan,MA Dan,LIN Lian-yun,et al.Crystal structure of the ryanodine receptor SPRY2 domain from the diamondback moth provides insights into the development of novel insecticides[J].J Agric Food Chem,2020,68:1731-1740.
- [4]LI Bin,XIANG Dong,CHAI Bao-shan,et al.Benzamide compounds and application thereof:WO2008134969A1[P].2008-11-13.
- [5]FENG Qi,LIU Zhi-li,XIONG Li-xia,et al.Synthesis and insecticidal activities of novel anthranilicdiamides containing modified N-pyridylpyrazoles[J].J Agric Food Chem,2010,58:12327-12336.
- [6]CLARK D A,FINKELSTEIN B L,LAHM G P,et al.Ortho-heterocyclic substituted aryl amides for controlling invertebrate pests:WO2003016304A1[P].2003-02-27.
- [7]MAO Ming-zhen,LI Yu-xin,LIU Xiao-xia,et al.Synthesis and insecticidal evaluation of novel N-pyridylpyrazolecarboxamides containing cyano substituent in the ortho-position[J].Bioorg Med Chem Lett,2013,23:42-46.
- [8]毛明珍,王伦,李正名,等.N-烷氧基(卤代烷基)酰基取代的邻苯二胺酰胺类化合物设计、合成与生物活性[J].农药,2018,57(11):802-806.
- [9]WU Chang-chun,YU Xiao-bo,WAGN Bao-lei,et al.Synthesis,insecticidal evaluation,and 3D-QASR of novel anthranilic diamide derivatives containing N-arylpyrrole as potential ryanodine receptor activators[J].J Agric Food Chem,2020,68:9319-9328.
- [10]LI Feng-yun,WANG Yuan-hong,LIU Jing-bo,et al.Synthesis,insecticidal evaluation and mode of action of novel anthranilic diamide derivatives containing sulfur moiety as potential ryanodine receptor activators[J].Bioorg Med Chem,2019,27:769-776.
- [11]WANG Bao-lei,ZHU Hong-wei,LI Zheng-ming,et al.One-pot synthesis,structure and structure-activity relationship of novel bioactive diphenyl/diethyl (3-bromo-1-(3-chloropyridin-2-yl)-1Hpyrazol-5-yl)(arylamino) methylphosphonates[J].Pest Manag Sci,2019,75:3273-7281.
- [12]ZHAO Yang-yang,GAO Li,LI Huan-gong,et al.Synthesis,insecticidal activities,and structure-activity relationship of phenylpyrazole derivatives containing a fluoro-substituted benzene moiety[J].J Agric Food Chem,2020,68(40):11282-11289.
- [13]WILES C,WATTS P,HASWELL S J.The use of electroosmotic flow as a pumping mechanism for semi-preparative scale continuous flow synthesis[J].Chem Commun,2007:966-968.
- [14]MATE E,MIRANDA V,CHRISTIAN S,et al.Chemistry and folding of photomodulable peptides-stilbene and thioaurone-type candidates for conformational switches[J].Org Biomol Chem,2008,6:4356-4373.
- [15]COUNCELLER C M,EICHMAN C C,WRAY B C,et al.Apractical,metal-free synthesis of 1H-indazoles[J].Org Lett,2008,10:1021-1023.
- [16]SEKI M,MORI Y,HATSUDA M,et al.A novel synthesis of(+)-biotin from L-cysteine[J].J Org Chem,2002,67:5527-5536.
- [17]GUDUDURU V,HURH E,DALTON J T,et al.Discovery of2-arylthiazolidine-4-carboxylic acid amides as a new class of cytotoxic agents for prostate cancer[J].J Med Chem,2005,48:2584-2588.
- [18]DONG Wei-li,XU Jun-ying,XIONG Li-xia,et al.Synthesis,structure and biological activities of some novel anthranilic acid esters containing N-pyridylpyrazole[J].Chin J Chem,2009,27:579-586.