Synthesis and Bioactivity Study of 2-Acylamino-Substituted N '-Benzylbenzohydrazide Derivatives

文献类型： 外文期刊

第一作者： Xu, Xibao

作者： Xu, Xibao;Rui, Changhui;Ou, Junjun;Zhu, Xiaokun;Wang, Lei;Xu, Chuan;Liu, Feng;Wang, Yi;Liu, Shangzhong

作者机构：

关键词： 2-acylamino-substituted N '-benzylbenzohydrazide derivatives;synthesis;insecticide

期刊名称：JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY （ 影响因子：5.279； 五年影响因子：5.269 ）

ISSN： 0021-8561

年卷期： 2012 年 60 卷 44 期

页码：

收录情况： SCI

摘要： The discovery of new safe and effective pesticides is one of the main means of providing eco-friendly agricultural agents for modern crop protection. To identify new biological molecules based of the anthranilic diamide skeleton of the novel pesticide chlorantraniliprole, which acts on the ryanodine receptor and functional groups in acyl hydrazine insect growth regulators, more than 40 new compounds of 2-acylamino-substituted N'-benzylbenzohydrazide derivatives were designed and synthesized. The structures of the new compounds were characterized using H-1 nuclear magnetic resonance (NMR), high-resolution mass spectrometry (HRMS), or electron impact mass spectrometry (El MS), and their biological activities at a concentration of 600 mg L-1 were determined against cotton aphid (Aphis gossypii Glover), carmine spider mite (Tetranychus cinnabarinus), and diamondback moth (Plutella xylostella). The results of a preliminary assay showed that compounds 6a-I-2 and 6d-III-4 maintained the lethal activity of anthranilic diamide against P. xylostella; compounds 6c-II-4, 6d-I-7, 6d-II-1, and 6d-III-5 exhibited good lethal activity against A gossypii; and compounds 6a-II-1, 6a-III-1, 6b-I-7, 6c-I-1, and 6c-III-5 retained promising larvicidal activities against T. cinnabarinus. In subsequent further tests against T. cinnabarinus, compounds 6a-II-1, 6a-III-1, 6c-I-1, and 6c-III-5 showed an LC50 value of <90 mg L-1; especially, the LC50 of compound 6a-III-1 was only 27.9 mg L-1. In conclusion, the introduction of the functional fragment-substituted acyl hydrazine improved the acaricidal activity of the anthranilic diamide skeleton, and the halogen atom at X position and the methyl group at RI play crucial roles in the biological activities of the compounds.

分类号：

  • 相关文献

[1]Target site insensitivity mutations in the AChE and LdVssc1 confer resistance to pyrethroids and carbamates in Leptinotarsa decemlineata in northern Xinjiang Uygur autonomous region. Jiang, Wei-Hua,Lu, Wei-Ping,Shi, Xiao-Qin,Xiong, Man-Hui,Wang, Zhi-Tian,Li, Guo-Qing,Guo, Wen-Chao.

[2]Synthesis and Bioactivity Evaluation of Anthranilic Diamide Derivatives as Green Potential Insecticides. Liu Genyan,Ju Xiulian,Yuan Huizhu,Yang Daibin. 2011

[3]Effects of pyrethroids on neuronal excitability of adult honeybees Apis mellifera. Zhang, Yi-Li,Sun, Ji-Hu,Zhou, Ting,Zhou, Wei,Wang, Qiang,Dai, Ping-Li,Liu, Feng,Zhou, Ting,Zhou, Wei,Wang, Qiang,Dai, Ping-Li.

[4]Toxicity of chlorantraniliprole to Cry1Ac-susceptible and resistant strains of Helicoverpa armigera. Lu, Qiong,Zhang, Lili,Guo, Fang,Liang, Gemei,Wu, Kongming,Guo, Yuyuan,Wyckhuys, Kris A. G..

[5]Increased expression of CSP and CYP genes in adult silkworm females exposed to avermectins. Xuan, Ning,Guo, Xia,Xie, Hong-Yan,Liu, Guo-Xia,Picimbon, Jean-Francois,Lou, Qi-Nian,Lu, Xing-Bo. 2015

[6]Using Next-Generation Sequencing to Detect Differential Expression Genes in Bradysia odoriphaga after Exposure to Insecticides. Chen, Haoliang,Lin, Lulu,Ali, Farman,Xie, Minghui,Zhang, Guangling,Su, Weihua,Ali, Farman. 2017

[7]Identification of glutathione S-transferases in Bemisia tabaci (Hemiptera: Aleyrodidae) and evidence that GSTd7 helps explain the difference in insecticide susceptibility between B.tabaci Middle East-Minor Asia 1 and Mediterranean. He, C.,He, C.,Xie, W.,Yang, X.,Wang, S. -L.,Wu, Q. -J.,Zhang, Y. -J.. 2018

[8]Identification and biochemical characterization of Laodelphax striatellus neutral ceramidase. Zhou, Y.,Lin, X. -W.,Zhang, Y. -R.,Huang, Y. -J.,Zhang, C. -H.,Yang, Q.,Yuan, J. -Q.,Cheng, J. -A.,Zhu, Z. -R.,Zhou, Y.,Lin, X. -W.,Zhang, Y. -R.,Huang, Y. -J.,Zhang, C. -H.,Yang, Q.,Yuan, J. -Q.,Cheng, J. -A.,Zhu, Z. -R.,Zhou, Y.,Xu, R.,Mao, C.,Li, H. -Y.,Yang, Q.. 2013

[9]Sublethal Effects of Insecticide Exposure on Megacopta cribraria (Fabricius) Nymphs: Key Biological Traits and Acetylcholinesterase Activity. Miao, Jin,Li, Guoping,Wu, Yuqing,Miao, Jin,Reisig, Dominic D.,Li, Guoping. 2016

[10]Joint toxicity of chlorpyrifos, atrazine, and cadmium at lethal concentrations to the earthworm Eisenia fetida. Yang, Guiling,Wang, Yanhua,Cai, Leiming,Wang, Qiang,Chen, Chen,Kong, Xiangzhen,Qian, Yongzhong.

[11]Recent progress of highly efficient in vivo biological screening for novel agrochemicals in China. Qian, Xuhong,Li, Baoju,Yuan, Huizhu,Fang, Jichao,Tao, Liming,Fan, Zhijin.

[12]The efficacies of 5 insecticides against hard ticks Hyalomma asiaticum, Haemaphysalis longicornis and Rhipicephalus sanguineus. Lu, Haiyan,Ren, Qiaoyun,Li, Youquan,Liu, Junlong,Niu, Qingli,Yin, Hong,Guan, Guiquan,Luo, Jianxun,Yin, Hong,Lu, Haiyan,Meng, Qingling.

[13]Mineralization of chlorpyrifos by co-culture of Serratia and Trichosporon spp.. Xu, Gangming,Li, Yingying,Zheng, Wei,Peng, Xiang,Li, Wen,Yan, Yanchun.

[14]Demographic Changes in Multigeneration Plutella xylostella (Lepidoptera: Plutellidae) After Exposure to Sublethal Concentrations of Spinosad. Yin, Xian-Hui,Wu, Qing-Jun,Zhang, You-Jun,Xu, Bao-Yun,Yin, Xian-Hui,Li, Xue-Feng,Wu, Qing-Jun.

[15]Effect of Six Insecticides on Three Populations of Bactrocera (Tetradacus) minax (Diptera: Tephritidae). Liu, Haoqiang,Jiang, Gaofei,Zhang, Yunfei,Chen, Fei,Li, Xiaojiao,Yue, Jiansu,Ran, Chun,Jiang, Gaofei,Chen, Fei,Zhao, Zhimo,Zhang, Yunfei,Li, Xiaojiao,Yue, Jiansu.

[16]Insecticide resistance in Bemisia tabaci biotype Q (Hemiptera: Aleyrodidae) from China. Luo, C.,Jones, C. M.,Devine, G.,Denholm, I.,Gorman, K.,Luo, C.,Zhang, F..

[17]Ternary toxicological interactions of insecticides, herbicides, and a heavy metal on the earthworm Eisenia fetida. Wang, Yanhua,Zhao, Xueping,Wang, Qiang,Chen, Chen,Qian, Yongzhong.

[18]Effect of chlorpyrifos on infectivity and survival of Steinernema feltiae. Chen, SL,Han, XY,Moens, M. 2003

[19]The growth and antioxidant defense responses of wheat seedlings to omethoate stress. Liang, Yongchao,Zhang, Bo,Chu, Guixin,Wei, Changzhou,Ye, Jun,Li, Zhiqiang,Zhang, Bo.

[20]Effect of heat shock on the susceptibility of Frankliniella occidentalis (Thysanoptera: Thripidae) to insecticides. Zuo Tai-qiang,Sun Li-juan,Wang Si-fang,Zheng Chang-ying,Wan Fang-hao,Wan Fang-hao,Li Hong-gang. 2016

作者其他论文 更多>>

微信小程序