Synthesis and Insecticidal Activity of 3-Arylisoxazoline-pyrazole-5-carboxamide Derivatives

doi:10.6023/cjoc201903056

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (9): 2655-2662.DOI: 10.6023/cjoc201903056 Previous Articles Next Articles

NOTE

3-芳基异噁唑啉-吡唑-5-甲酰胺类化合物的合成及杀虫活性研究

钟良坤^a,b, 江涛^a, 张帆^a, 付庆^a, 刘幸海^a, 许天明^b, 丁成荣^a, 陈杰^c, 袁静^c, 谭成侠^a

a 浙江工业大学化学工程学院杭州 310014;
b 浙江省化工研究院有限公司杭州 310023;
c 浙江农林大学林业与生物技术学院杭州 311300

收稿日期:2019-03-26 修回日期:2019-04-19 发布日期:2019-05-15
通讯作者: 袁静, 谭成侠 E-mail:1015251265@qq.com;tanchengxia@zjut.edu.cn
基金资助:
国家重点研发计划（No.2017YFD0200507）资助项目.

Synthesis and Insecticidal Activity of 3-Arylisoxazoline-pyrazole-5-carboxamide Derivatives

Zhong Liangkun^a,b, Jiang Tao^a, Zhang Fan^a, Fu Qing^a, Liu Xinghai^a, Xu Tianming^b, Ding Chengrong^a, Chen Jie^c, Yuan Jing^c, Tan Chengxia^a

a College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014;
a Zhejiang Research Institute of Chemical Industry. Ltd., Hangzhou 310023;
b School of Forestry and Biotechnology, Zhejiang A & F University, Hangzhou 311300

Received:2019-03-26 Revised:2019-04-19 Published:2019-05-15
Contact: 10.6023/cjoc201903056 E-mail:1015251265@qq.com;tanchengxia@zjut.edu.cn
Supported by:
Project supported by the National Key Research and Development Plan (No. 2017YFD0200507).

1. Synthesis and Insecticidal Activity of 3-Arylisoxazoline-pyrazole-5-carboxamide Derivatives.PDF(640KB)

Abstract

A series of 3-arylisoxazoline-pyrazole-5-carboxamide derivatives derived from ethyl 5,5-dimethoxy-2,4-dioxopentanoate were designed, synthesized, and characterized by ¹H NMR, ¹³C NMR and HRMS. The preliminary bioassay indicated that most title compounds exhibited positive potency against Mythimna separate (Walker) at 500 mg/L. At the concentration of 100 mg/L, three compounds were still moderately active against Mythimna separate (Walker) (lethal rate≈60%). At 500 mg/L, four compounds were also active against Aphis craccivora. The results indicated that the potential of these 3-arylisoxazoline-pyrazole-5-carboxamide derivatives can be utilized in insecticide research with further optimization.

Key words: arylisoxazoline, pyrazole-5-carboxamide, synthesis, insecticidal activity

Cite this article

Zhong Liangkun, Jiang Tao, Zhang Fan, Fu Qing, Liu Xinghai, Xu Tianming, Ding Chengrong, Chen Jie, Yuan Jing, Tan Chengxia. Synthesis and Insecticidal Activity of 3-Arylisoxazoline-pyrazole-5-carboxamide Derivatives[J]. Chin. J. Org. Chem., 2019, 39(9): 2655-2662.

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[1] Pirol, S.-C.; Caliskan, B.; Durmaz, I.; Atalay, R.; Banoglu, E. Eur. J. Med. Chem. 2014, 87, 140.
[2] Gong, C.-C.; Tan, H.-Y.; Zhang, Q. Chin. J. Org. Chem. 2018, 38, 3086(in Chinese). (龚超超, 谈寒一, 张倩, 有机化学, 2018, 38, 3086.)
[3] He, B.; Wang, D.-W.; Yang, W.-C.; Chen, Q.; Yang, G.-F. Chin. J. Org. Chem. 2017, 37, 2895(in Chinese). (何波, 王大伟, 杨文超, 陈琼, 杨光富, 有机化学, 2017, 37, 2895.)
[4] Li, Y.-X.; Liu, S.-H.; Li, Y.-H.; Song, H.-B.; Wang, Q.-M. Bioorg. Med. Chem. Lett. 2009, 19, 2953.
[5] Bizikova, P.; Linder, K.; Olivry, T. Vet. Dermatol. 2014, 25, 103.
[6] Aloisi, A.; Franchet, A.; Ferrandon, D.; Bianco, A.; Moyon, C. Bioorg. Med. Chem. Lett. 2018, 28, 2631.
[7] Xiong, L.; Li, H.; Jiang, L.-N.; Ge, J.-M.; Yang, W.-C.; Zhu, X.-L.; Yang, G.-F. J. Agric. Food Chem. 2017, 65, 1021.
[8] Sun, N.-B.; Shen, Z.-H.; Zhai, Z.-W.; Han, L.; Weng, J.-Q.; Tan, C.-X.; Liu, X.-H. Chin. J. Org. Chem. 2017, 37, 2705(in Chinese). (孙娜波, 沈钟华, 翟志文, 韩亮, 翁建全, 谭成侠, 刘幸海, 有机化学, 2017, 37, 2705.)
[9] Li, X.-H.; Zhi, L.-P.; Song, B.-A.; Xu, H.-L. Chem. Res. Chin. Univ. 2008, 24, 454.
[10] Shi, Y.-J.; Zhou, Q.; Wang, Y.; Qian, H.-W.; Ye, L.-Y.; Feng, X.; Chen, H.; Li, Y.-T.; Dai, H.; Wei, Z.-H.; Wu, J.-M. Chin. J. Org. Chem. 2018, 38, 2450(in Chinese). (石玉军, 周钱, 王杨, 钱宏炜, 叶林玉, 冯霞, 陈辉, 李雅婷, 戴红, 魏中昊, 吴锦明, 有机化学, 2018, 38, 2450.)
[11] Zhang, X.-L.; Wang, B.-L.; Mao, M.-Z.; Xiong, L.-X.; Yu, S.-J.; Li, Z.-M. Chem. J. Chin. Univ. 2013, 34, 96(in Chinese). (张秀兰, 王宝雷, 毛明珍, 熊丽霞, 于淑晶, 李正名, 高等学校化学学报, 2013, 34, 96.)
[12] Song, H.-J.; Liu, Y.-X.; Xiong, L.-X.; Li, Y.-Q.; Yang, N.; Wang, Q.-M. J. Agric. Food Chem., 2013, 61, 8730.
[13] Zhao, Y.; Li, Y.-Q.; Xiong, Li.-X.; Xu, L.-P.; Peng, L.-N.; Li, F.; Li, Z.-M. Chem. Res. Chin. Univ. 2013, 29, 51.
[14] Grossmann, K.; Ehrhardt, T. Pest. Manage. Sci. 2007, 63, 429.
[15] Yang, S.-G.; Hao, G.-F.; Dayan, F.-E.; Tranel, P.; Yang, G.-F. Chin. J. Chem. 2013, 31, 1153.
[16] Monicka, J.; James, C. J. Mol. Struct. 2014, 1075, 335.
[17] Chen, X.-L.; Xiao, Y.-X.; Wang, G.-L.; Li, Z.; Xu, X.-Y. Res. Chem. Intermed. 2016, 42, 5495.
[18] Meanwell, N. J. Med. Chem. 2011, 54, 2529.
[19] Lingaraju, G.; Balaji, K.; Jayarama, S.; Anil, S.; Kiran, K.; Sa-dashiva, M. Bioorg. Med. Chem. Lett. 2018, 28, 3606.
[20] Loh, B.; Vozzolo, L.; Mok, B.; Lee, C.-C.; Fitzmaurice, R.; Caddick, S.; Fassati, A. Chem. Biol. Drug. Des. 2010, 75, 461.
[21] Talley, J.; Brown, D.; Carter, J.; Graneto, M.; Koboldt, C.; Masferrer, J.; Perkins, W.; Rogers, R.; Shaffer, A.; Zhang, Y.-Y.; Zweifel, B.; Seibert, K. J. Med. Chem. 2000, 43, 775.
[22] Brahmayya, M.; Venkateswararao, B.; Krishnarao, D.; Durgarao, S.; Prasad, U.; Damodharam, T.; Mishra, R. J. Pharm. Res. 2013, 7, 516.
[23] Fang, F. Ph.D. Dissertation, Guangxi University, Nanning, 2016(in Chinese). (方芳, 博士论文, 广西大学, 南宁, 2016.)
[24] Pascal, B.; Gopal, D.; Wolfgang, V.; Matthias, P.; Franz, J. B. WO 2016102482, 2016[Chem. Abstr. 2016, 165, 152398].
[25] Shoop, W.; Hartline, E.; Gould, B.; Waddell, M.; McDowell, R.; Kinney, J.; Lahm, G.; Long, J.; Xu, M.; Wagerle, T.; Jones, G.; Dietrich, R.; Cordova, D.; Schroeder, M.; Rhoades, D.; Benner, E.; Confalone, P. Vet. Parasitol. 2014, 201, 179.
[26] Ishaaya, I.; Horowitz, A. R. In Insecticides with Novel Modes of Action:Mechanisms and Application, Eds.:Ishaaya, I.; Degheele, D., Springer, Berlin, 1998, p. 152.
[27] Semple, G.; Gharbaoui, T.; Shin, Y.; Decaire, M.; Averbuj, C.; Skinner, P. US 20070032537, 2007[Chem. Abstr. 2007, 142, 219276].
[28] Martins, M.; Sinhorin, A.; Frizzo, C.; Buriol, L.; Scapin, E.; Zanatta, N.; Bonacorso, H. J. Heterocycl. Chem. 2013, 50, 71.
[29] Jagannath, M.; Madhavan, G.; Shanmugam, P. WO 2014202580, 2014[Chem. Abstr. 2014, 162, 137571].
[30] Liu, T.-T.; Ni, Y.; Zhong, L.-K.; Huang, H.-Y.; Hu, W.-Q.; Xu, T.-M.; Tan, C.-X. Chin. J. Org. Chem. 2015, 35, 422(in Chinese). (刘婷婷, 倪芸, 钟良坤, 黄红英, 胡伟群, 许天明, 谭成侠, 有机化学, 2015, 35, 422.)

3-芳基异噁唑啉-吡唑-5-甲酰胺类化合物的合成及杀虫活性研究

Synthesis and Insecticidal Activity of 3-Arylisoxazoline-pyrazole-5-carboxamide Derivatives

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