新型含1,3,4-噁二唑结构的吡唑酰胺类化合物的合成与杀虫活性研究
收稿日期: 2017-02-07
修回日期: 2017-03-07
网络出版日期: 2017-03-17
基金资助
国家自然科学基金（No.21372135）、江苏省"六大人才高峰"（No.2013-SWYY-013）、南通市科技计划（No.MS22015020）、江苏省大学生创新训练计划（No.201610304047Z）和南通大学研究生科研创新计划（No.YKC16086）资助项目.
Synthesis and Insecticidal Activities of Novel Pyrazole Amides Containing 1,3,4-Oxadiazole Moiety
Received date: 2017-02-07
Revised date: 2017-03-07
Online published: 2017-03-17
Supported by
Project supported by the National Natural Science Foundation of China (No.21372135),the Research Foundation of the Six People Peak of Jiangsu Province (No.2013-SWYY-013),the Science and Technology Project Fund of Nantong City (No.MS22015020),the Science and Technology Innovation Foundation for the College Students of Jiangsu Province (No.201610304047Z) and the Science and Technology Innovation Foundation for the Graduate Students of Nantong University (No.YKC16086).
为了寻找与发现新的活性物质，以杀虫剂吡螨胺为先导化合物，采用活性基团拼接的方法，设计并制备了一系列未见文献报道的新型含1，3，4-噁二唑结构的吡唑酰胺类化合物.通过1H NMR，13C NMR和元素分析测试确认了目标化合物的结构.初步的生物活性测试结果显示，部分目标化合物表现出较好的杀虫活性.在测试浓度为500 μg/mL时，有5个化合物对粘虫的杀灭活性可达80%~100%，其中4个化合物对粘虫的防治效果与对照药剂唑虫酰胺接近.此外，1-甲基-3-乙基-4-氯-N-{[5-（4-甲基苯基）-1，3，4-噁二唑-2-基]甲基}-1H-吡唑-5-甲酰胺（9g）在测试浓度为500 μg/mL时对蚜虫的杀死率为100%.
石玉军 , 叶林玉 , 仲苏林 , 曹雄飞 , 戴红 , 洪宇 , 李春建 , 石健 , 吴锦明 . 新型含1,3,4-噁二唑结构的吡唑酰胺类化合物的合成与杀虫活性研究[J]. 有机化学, 2017 , 37(7) : 1844 -1849 . DOI: 10.6023/cjoc201702006
In order to find new pesticide with potent bioactivities, a series of novel pyrazole amides carrying 1,3,4-oxadiazole moiety were prepared according to the structure of tebufenpyrad. The structures of the title compounds were characterized by 1H NMR, 13C NMR and elemental analysis. Preliminary bioassay data showed that some target compounds displayed good insecticidal activities. At the concentration of 500 μg/mL, five compounds had insecticidal activity against Oriental armyworm with 80%~100%, and four compounds displayed comparable insecticidal activity against Oriental armyworm to that of the control tolfenpyrad. In addition, 1-methyl-3-ethyl-4-chloro-N-{[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl)methyl]-1H-pyrazole-5-carboxamide (9g) exhibited 100% insecticidal activity against Aphis medicaginis at 500 μg/mL.
Key words： 1,3,4-oxadiazole; pyrazole; synthesis; insecticidal activity
[1] Li, Y.; Zhang, H. Q.; Liu, J.; Yang, X. P.; Liu, Z. J. J. Agric. Food Chem. 2006, 54, 3636.
[2] Dai, H.; Zhuang. H. Y.; Shi, L.; Li, G.; Zhang, H. J.; Fang, Y.; Dai, B. J. Chin. J. Org. Chem. 2015, 35, 2399(in Chinese). (戴红, 庄辉阳, 施磊, 李刚, 张海军, 方源, 戴宝江, 有机化学, 2015, 35, 2399.)
[3] Dai, H.; Li, H.; Jin. Z. C.; Liu, W. Y.; Xiao, Y.; He, H. B.; Wang, Q. M.; Shi, Y. J. Chin. J. Org. Chem. 2016, 36, 185(in Chinese). (戴红, 李宏, 金智超, 刘文永, 肖瑶, 何海兵, 汪清民, 石玉军, 有机化学, 2016, 36, 185.)
[4] Park, H. J.; Lee, K.; Park, S. J.; Ahn, B.; Lee, J. C.; Cho, H. Y.; Lee, K. I. Bioorg. Med. Chem. Lett. 2005, 15, 3307.
[5] Zheng, J.; Chen, Y.; Wu, K. L.; Ran, C. L.; Xu, Y.; Song, M. P. Chin. J. Org. Chem. 2013, 33, 1536(in Chinese). (郑娟, 陈雨, 吴孔丽, 冉春玲, 徐琰, 宋毛平, 有机化学, 2013, 33, 1536.)
[6] Huang, Q. C.; Qian, X. H.; Song, G. H.; Cao, S. Pest Manage. Sci. 2003, 59, 933.
[7] Wang, B. L.; Li, Z. M.; Li, Y. H.; Wang, S. H. Chem. J. Chin. Univ. 2008, 29, 90(in Chinese). (王宝雷, 李正名, 李永红, 王素华, 高等学校化学学报, 2008, 29, 90.)
[8] Ruan, L. L.; Fan, R. J.; Liu, X. H.; Chen, J.; Weng, J. Q. Chin. J. Org. Chem. 2015, 35, 1166(in Chinese). (阮铃莉, 范人杰, 刘幸海, 陈杰, 翁建全, 有机化学, 2015, 35, 1166.)
[9] Formagio, A. S. N.; Tonin, L. T. D.; Foglio, M. A.; Madjarof, C.; Carvalho. J. E. D.; Costa, W. F. D.; Cardoso, F. P.; Sarragiotto, M. H. Bioorg. Med. Chem. 2008, 16, 9660.
[10] Zheng, X. M.; Zhong, L.; Wang, Y. L.; Chen, W. D.; Huang, Q. C.; Liu, C. X.; Song, G. H. J. Fluorine Chem. 2003, 123, 163.
[11] Shi, Y. J.; Li, Y.; Fang, Y.; Chen, J.; Ye, L. Y.; Ge, S. S.; Dai, H. Chin. J. Org. Chem. 2016, 36, 2472(in Chinese). (石玉军, 李阳, 方源, 陈佳, 叶林玉, 葛书山, 戴红, 有机化学, 2016, 36, 2472.)
[12] Dai, H.; Li, Y. Q.; Du, D.; Qin, X.; Zhang, X.; Yu, H. B.; Fang, J. X. J. Agric. Food Chem. 2008, 56, 10805.
[13] Hamaguchi, H.; Kajihara, O.; Katoh, M. J. Pestic. Sci. 1995, 20, 173.
[14] Motoba, K.; Nishizawa, H.; Suzuki, T.; Hamaguchi, H.; Uchida, M.; Funayama, S. Pestic. Biochem. Physiol. 2000, 67, 73.
[15] Swanson, M. B.; Ivancic, W. A.; Saxena, A. M.; Allton, J. D.; O'Brien, G. K.; Suzuki, T.; Nishizawa, H.; Nokata, M. J. Agric. Food Chem. 1995, 43, 513.
[16] Lahm, G. P.; Selby, T. P.; Freudenberger, J. H.; Stevenson, T. M.; Myers, B. J.; Seburyamo, G.; Smith, B. K.; Flexner, L.; Clark, C. E.; Cordova, D. Bioorg. Med. Chem. Lett. 2005, 15, 4898.
[17] Gu, B. Q.; Zhu, W. Q.; Fan, W. Z.; Qian, H.; Liu, J. M.; Zhang, A. Q.; Shen, R. X. Mod. Agrochem. 2002, 1, 9(in Chinese). (顾保权, 朱伟清, 范文政, 钱虹, 刘建梅, 张爱庆, 沈荣仙, 现代农药, 2002, 1, 9.)
[18] Fan, W. Z.; Gu, B. Q.; Zhu, W. Q.; Zhang, Y. B. Mod. Agrochem. 2005, 4, 9(in Chinese). (范文政, 顾保权, 朱伟清, 张一宾, 现代农药, 2005, 4, 9.)
[19] Wang, Z. J.; Liu, B.; Li, Y. H.; Zhao, W. G. Chin. J. Org. Chem. 2011, 31, 317(in Chinese). (王振军, 刘斌, 李永红, 赵卫光, 有机化学, 2011, 31, 317.)
[20] Dai, H.; Liu, J. B.; Miao, W. K.; Wu, S. S.; Zhang, X.; Wang, T. T.; Fang, J. X. Chin. J. Org. Chem. 2011, 31, 1943(in Chinese). (戴红, 刘建兵, 苗文科, 吴珊珊, 张欣, 王婷婷, 方建新, 有机化学, 2011, 31, 1943.)
[21] Wang, H. S.; Zhao, W. X. Chin. J. Org. Chem. 2013, 33, 1822(in Chinese). (王宏社, 赵卫星, 有机化学, 2013, 33, 1822.)
[22] Sheng, G. Z.; Zhang, W. Chin. J. Org. Chem. 2013, 33, 2271(in Chinese). (盛国柱, 张炜, 有机化学, 2013, 33, 2271.)
[23] Wei, F.; Zhao, B. X.; Huang, B.; Zhang, L.; Sun, C. H.; Dong, W. L.; Shin, D. S.; Miao, J. Y. Bioorg. Med. Chem. Lett. 2006, 16, 6342.
[24] Song, H. J.; Liu, Y. X.; Xiong, L. X.; Li, Y. Q.; Yang, N.; Wang, Q. M. J. Agric. Food Chem. 2013, 61, 8730.
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