Design, synthesis and insecticidal activities of novel pyrazole amides containing hydrazone substructures
Design, synthesis and insecticidal activities of novel pyrazole amides containing hydrazone substructures
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含腙结构的新型吡唑酰胺的设计、合成及其杀虫活性
DOI：
10.1002/ps.2329
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发表时间：
2012-05-01
影响因子：
4.1
通讯作者：
Yang, Song
中科院分区：
文献类型：
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作者：
Wu, Jian;Song, Bao-An;Yang, Song
背景：吡唑和腙类化合物具有良好的杀虫活性，其亚结构单元在农药设计中有着广泛的应用。为了寻找具有良好杀虫活性的新化合物，合成了一系列含腙结构的吡唑酰胺衍生物，并进行了生物活性测定。生物活性测定结果表明，部分化合物对小菜蛾有较好的防治效果（Linnaeus）、棉铃虫（Helicoverpa armigera（Hubner））、淡色库蚊（Culex pipiens pallens）、甜菜夜蛾（Laphygma exigua（Hubner））、斜纹夜蛾（Spodoptera litura（Fabricius）、褐飞虱（Nilaparvata lugens）和麦蚜（Rhopalosiphum majenum）的浓度分别为5、10、0.25、200、20、100和500 mg L-1。用比较分子场分析法（CoMFA）对小菜蛾的生物活性进行了研究，CoMFA模型的q（2）和r（2）值分别为0.701和0.964。结论：部分目标化合物对不同种类的昆虫表现出较好的广谱杀虫活性; CoMFA模型揭示了苯的4-位上的大体积且带负电荷的基团可以增强杀虫活性。这些结果可为设计含吡唑酰胺和腙亚结构单元的新型杀虫剂提供有用的信息。(C)2011年化学工业协会
BACKGROUND: Pyrazole and hydrazone derivatives possess good insecticidal activities; their substructural units are widely used in pesticide design. In an effort to discover new molecules with good insecticidal activities, a series of pyrazole amide derivatives containing hydrazone substructures were synthesised and bioassayed.RESULTS: Bioassays demonstrated that some of the title compounds exhibited notable control of Plutella xylostella (Linnaeus), Helicoverpa armigera (Hubner), Culex pipiens pallens, Laphygma exigua (Hubner), Spodoptera litura (Fabricius), Nilaparvata lugens (Stal) and Rhopalosiphum maidis (Fitch) at 5, 10, 0.25, 200, 20, 100 and 500 mg L-1 respectively. Comparative molecular field analysis (CoMFA) based on the bioactivities for P. xylostella was studied; the values of q(2) and r(2) for the CoMFA model were 0.701 and 0.964 respectively.CONCLUSION: Some of the title compounds displayed good and broad-spectrum insecticidal activities against different insect species; the CoMFA model revealed that a bulky and negatively charged group at the 4-position of benzene could enhance insecticidal activity. These results could provide useful information for the design of novel insecticide containing substructural units of pyrazole amide and hydrazone. (C) 2011 Society of Chemical Industry