Synthesis and Biological Activity of Diamide Compounds

doi:10.6023/cjoc201909023

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (3): 782-786.DOI: 10.6023/cjoc201909023 Previous Articles Next Articles

双酰胺类化合物的合成及生物活性研究

杨森, 邹文倩, 陶敏, 马天扬, 刘幸海, 翁建全, 谭成侠

浙江工业大学化学工程学院杭州 310014

收稿日期:2019-09-16 修回日期:2019-10-18 发布日期:2019-11-07
通讯作者: 谭成侠 E-mail:tanchengxia@zjut.edu.cn
基金资助:
国家重点研发计划（No.2017YFD0200507）资助项目.

Synthesis and Biological Activity of Diamide Compounds

Yang Sen, Zou Wenqian, Tao Min, Ma Tianyang, Liu Xinghai, Weng Jianquan, Tan Chengxia

College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014

Received:2019-09-16 Revised:2019-10-18 Published:2019-11-07
Supported by:
Project supported by the National Key R&D Program (No. 2017YFD0200507).

1. 200782S.pdf.pdf(2488KB)

Abstract

In order to find pesticidal lead compounds with high activity, a series of novel diamide compounds were designed and synthesized by using metalaxyl as a leading compound, as well as the principle of active substructure combination. The structures of the target compounds were confirmed by ¹H NMR, ¹³C NMR and HRMS. The preliminary bioassay showed that compound 5j showed an 85% inhibition rate against Pseudoperoniospora cubensis at 50 mg/L, most of the target compounds had good insecticidal activity against Oriental armyworm at 500 mg/L, and compounds 5b, 5f, 5g, 5h, 5i and 5l have a mortality rate of 100% against Oriental armyworm. At 250 mg/L, the mortality rate of compounds 5f, 5h and 5l against Oriental armyworm was 50%.

Key words: diamide compound, synthesize, biological activity

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Yang Sen, Zou Wenqian, Tao Min, Ma Tianyang, Liu Xinghai, Weng Jianquan, Tan Chengxia. Synthesis and Biological Activity of Diamide Compounds[J]. Chinese Journal of Organic Chemistry, 2020, 40(3): 782-786.

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[1] Zhao, W.; Xing, J. H.; Xu, T. M.; Peng, W. L.; Liu, X. H. Front. Chem. Sci. Eng. 2017, 11, 363.
[2] Zhao, W.; Shen, Z. H.; Xu, T. M.; Peng, W. L.; Liu, X. H. J. Hetero- cycl. Chem. 2017, 54, 1751.
[3] Cheng, L.; Shen, Z. H.; Xu, T. M.; Tan, C. X.; Weng, J. Q.; Han, L.; Peng, W. L.; Liu. X. H. J. Heterocycl. Chem. 2018, 55, 946.
[4] Zhong, L. K.; Jiang, T.; Zhang, F.; Fu, Q.; Liu, X. H.; Xu, T. M.; Ding, C. R.; Chen, J.; Yuan, J.; Tan, C. X. Chin. J. Org. Chem. 2019, 39, 2655(in Chinese). (钟良坤, 江涛, 张帆, 付庆, 刘幸海, 许天明, 丁成荣, 陈杰, 袁静, 谭成侠, 有机化学, 2019, 39, 2655.)
[5] Zhao, W.; Shen, Z. H.; Xing, J. H.; Yang, G.; Xu, T. M.; Peng, W. L.; Liu, X. H. Chem. Pap. 2017, 71, 921.
[6] Yang, Z. B.; Hu, D. Y.; Zeng, S.; Song, B. A. Bioorg. Med. Chem. Lett. 2016, 26, 1161.
[7] Ding, C. R.; Pan, Y. Y.; Yin, X.; Tan, C. X. Chin. J. Org. Chem. 2019, 39, 2099(in Chinese). (丁成荣, 潘亚运, 殷许, 谭成侠, 有机化学, 2019, 39, 2099.)
[8] Zhao, W.; Shen, Z. H.; Xing, J. H.; Xu, T. M.; Peng, W. L.; Liu, X. H. Chin. J. Struct. Chem. 2017, 36, 423.
[9] Liu, X. H.; Qiao, L.; Zhai, Z. W.; Cai, P. P.; Cantrell, C. L.; Tan, C. X.; Weng, J. Q.; Han, L.; Wu, H. K. Pest Manage. Sci. 2019, 75, 2892.
[10] Xu, L.Y. CN 108516955, 2018[Chem. Abstr. 2018, 169, 428795].
[11] Sun, N. B.; Shi, Y. X.; Liu, X. H.; Ma, Y.; Tan, C. X.; Weng, J. Q.; Jin, J. Z.; Li, B. J. Int. J. Mol. Sci. 2013, 14, 21741.
[12] Duan, L. P.; Zhao, Q. F.; Zhang, H. B. Arabian J. Chem. 2010, 3, 225.
[13] Liu, D. W.; Cheng, L. Z.; Chang, Q.; Dong, H. L.; Zhu, R. Y.; Gu, J. K. CN 106632122, 2017[Chem. Abstr. 2017, 167, 30990].
[14] Vishnoi, S.; Agrawal, V.; Kasana, V. K. J. Agric. Food Chem. 2009, 57, 3261.
[15] Liu, M.; Wang, Y.; Liu, F.; Cui, Y. L.; Duan, Y. S. J. Agric. Food Chem. 2010, 58, 6858.
[16] Easton, G. D.; Nagle, M. E. Am. Potato J. 1984, 61, 83.
[17] Zheng, L. Y.; Zhang, S. Q.; Xie, Y. C.; Ding, Z. Y.; Zhu, X. F. CN 101088986, 2007[Chem. Abstr. 2007, 148, 121450].
[18] Grieder, A.; Coers, K. J.; Labuhn, P. US 4267356, 1981[Chem. Abstr. 1981, 95, 81542].
[19] Nagy, L; Pelyva, J.; Agocs, P.; Soptei, C.; Kolonics, Z.; Benczik, J.; Balini, S.; Sebok, D.; Cseke, J. WO 9320041, 1994[Chem. Abstr. 1994, 120, 134058].
[20] Molchanov, L. V.; Aripov, K. N.; Khalikov, S.-S.; Gorovits, T. T. Uzb. Khim. Zh. 1990, 1, 27.
[21] Yang, S.; Ding, C. R.; Liu, X. H.; Weng, J. Q.; Yuan, J.; Tang, C. X. Chin. J. Org. Chem. 2019, 39, 3588(in Chinese). (杨森, 丁成荣, 刘幸海, 翁建全, 袁静, 谭成侠, 有机化学, 2019, 39, 3588.)
[22] Liu, X. H.; Tan, C. X.; Weng, J. Q. Phosphorus, Sulfur, Silicon Relat. Elem. 2011, 186, 558.

双酰胺类化合物的合成及生物活性研究

Synthesis and Biological Activity of Diamide Compounds

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