Design, synthesis and insecticidal evaluation of aryloxy dihalopropene derivatives.

作者: Ji-Chun Yang , Miao Li , Qiao Wu , Chang-Ling Liu , Xiu-Hui Chang

DOI: 10.1016/J.BMC.2015.09.030

关键词:

摘要: Plutella xylostella (P. xylostella) is a highly migratory, cosmopolitan species and one of the most important pest cruciferous crops worldwide. Pyridalyl as novel class insecticides has good efficacy against P. xylostella. On basis commercial insecticide pyridalyl, series new aryloxy dihalopropene derivatives were designed synthesized by using Intermediate Derivatization Methods. Their chemical structures confirmed (1)H NMR, high-resolution mass spectrum (HRMS), single-crystal X-ray diffraction analysis. The insecticidal activities compounds evaluated. results bioassays indicated that showed moderate to high at tested concentration, especially 10e 10g displayed more than 75% activity 6.25mg/L, while pyridalyl 50% same concentration. field trials result compound 10% emulsifiable concentrate (EC) was effective in control 75-150g a.i./ha, mortality for treatment with 75g a.i./ha equivalent 105g a.i./ha.

参考文章(18)
Hui-Chao Li, Chang-Ling Liu, Bao-Shan Chai, Miao Li, Zhi-Nian Li, Ji-Chun Yang, Design, synthesis and fungicidal activity of novel strobilurin analogues containing substituted N-phenylpyrimidin-2-amines. Natural Product Communications. ,vol. 4, pp. 1209- 1214 ,(2009) , 10.1177/1934578X0900400911
Miao Li, Chang-Ling Liu, Jing Zhang, Qiao Wu, Shu-Lin Hao, Yu-quan Song, Design, synthesis and structure-activity relationship of novel insecticidal dichloro-allyloxy-phenol derivatives containing substituted pyrazol-3-ols. Pest Management Science. ,vol. 69, pp. 635- 641 ,(2013) , 10.1002/PS.3417
Noriyasu Sakamoto, Shigeru Saito, Taro Hirose, Masaya Suzuki, Sanshiro Matsuo, Keiichi Izumi, Toshio Nagatomi, Hiroshi Ikegami, Kimitoshi Umeda, Kazunori Tsushima, Noritada Matsuo, The discovery of pyridalyl: a novel insecticidal agent for controlling lepidopterous pests. Pest Management Science. ,vol. 60, pp. 25- 34 ,(2004) , 10.1002/PS.788
John G Topliss, None, Utilization of operational schemes for analog synthesis in drug design Journal of Medicinal Chemistry. ,vol. 15, pp. 1006- 1011 ,(1972) , 10.1021/JM00280A002
Miao Li, Chang-Ling Liu, Lin Li, Hao Yang, Zhi-Nian Li, Hong Zhang, Zheng-Ming Li, Design, synthesis and biological activities of new strobilurin derivatives containing substituted pyrazoles Pest Management Science. ,vol. 66, pp. 107- 112 ,(2010) , 10.1002/PS.1837
Hui Chao Li, Bao Shan Chai, Zhi Nian Li, Ji Chun Yang, Chang Ling Liu, Synthesis and fungicidal activity of novel strobilurin analogues containing substituted N-phenylpyrimidin-2-amines Chinese Chemical Letters. ,vol. 20, pp. 1287- 1290 ,(2009) , 10.1016/J.CCLET.2009.05.028
Aiying Guan, Changling Liu, Guang Huang, Huichao Li, Shulin Hao, Ying Xu, Yong Xie, Zhinian Li, Synthesis and fungicidal activity of fluorine-containing chlorothalonil derivatives Journal of Fluorine Chemistry. ,vol. 160, pp. 82- 87 ,(2014) , 10.1016/J.JFLUCHEM.2014.01.006
Ai-Ying Guan, Chang-Ling Liu, Guang Huang, Hui-Chao Li, Shu-Lin Hao, Ying Xu, Zhi-Nian Li, Design, synthesis, and structure-activity relationship of novel aniline derivatives of chlorothalonil. Journal of Agricultural and Food Chemistry. ,vol. 61, pp. 11929- 11936 ,(2013) , 10.1021/JF403739E
Ai Ying Guan, Chang Ling Liu, Zhi Nian Li, Ming Xing Zhang, Synthesis and bioactivity of novel coumarin derivatives containing (E)-methyl 2-(methoxyimino)-2-phenylacetates Chinese Chemical Letters. ,vol. 22, pp. 663- 666 ,(2011) , 10.1016/J.CCLET.2010.12.028
Aiying Guan, Changling Liu, Xiaoping Yang, Mark Dekeyser, Application of the Intermediate Derivatization Approach in Agrochemical Discovery Chemical Reviews. ,vol. 114, pp. 7079- 7107 ,(2014) , 10.1021/CR4005605