Study on the Synthesis and Insecticidal Activity of Spinosyn A Derivatives

doi:10.6023/cjoc201807001

Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (12): 3363-3372.DOI: 10.6023/cjoc201807001 Previous Articles Next Articles

Notes

多杀菌素A衍生物的合成及其生物活性研究

张凯^a, 李加荣^a, 温都苏^a, 刘洪林^b, 王海邮^b, 阿拉木斯^b

a 北京理工大学化学与化工学院北京 100081;
b 中国农业科学院草原研究所呼和浩特 010000

收稿日期:2018-07-01 修回日期:2018-08-02 发布日期:2018-09-05
通讯作者: 李加荣 E-mail:jrli@bit.edu.cn
基金资助:
国家自然科学基金（No.41471198）资助项目.

Study on the Synthesis and Insecticidal Activity of Spinosyn A Derivatives

Zhang Kai^a, Li Jiarong^a, Wen Dusu^a, Liu Honglin^b, Wang Haiyou^b, A Lamusi^b

a School of Chemistry and Chemical Engineering, Beijing Institute of Technology, Beijing 100081;
b Institute of Grassland Research of Chinese Academy of Agricultural Sciences, Hohhot 010000

Received:2018-07-01 Revised:2018-08-02 Published:2018-09-05
Contact: 10.6023/cjoc201807001 E-mail:jrli@bit.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 41471198).

1. Study on the Synthesis and Insecticidal Activity of Spinosyn A Derivatives.PDF(7471KB)

Abstract

Spinosyns are a novel kind of biopesticide produced by Saccharopolyspora spinosa. Spinosyns have been widely applied in pest control because of their broad insecticidal spectrum, high insecticidal activity, low environmental impact, and low toxicity. To identify spinosyn compounds with improved insecticidal activity, a series of D-forosamine replacement derivatives of spinosyn A were synthesized. The insecticidal activities of the synthetic derivatives were evaluated against 3rd-instar larvae of Plutella xylostella. All derivatives exhibited good insecticidal activity to P. xylostella.

Key words: natural product, spinosyn A, semi-synthetic derivative, insecticidal activity

Cite this article

Zhang Kai, Li Jiarong, Wen Dusu, Liu Honglin, Wang Haiyou, A Lamusi. Study on the Synthesis and Insecticidal Activity of Spinosyn A Derivatives[J]. Chin. J. Org. Chem., 2018, 38(12): 3363-3372.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Deng, X. L.; Zhang, L.; Hu, X. P.; Yin, B.; Liang P.; Yang, X. L. Chin. Chem. Lett. 2016, 27, 251.
[2] Liu, Y.; Lei, C.; Xu, X. Y.; Shao, X. S.; Li, Z. Chin. Chem. Lett. 2016, 27, 321.
[3] Lahm, G. P.; Cordova, D.; Barry, J. D. Med. Chem. 2009, 17, 4127.
[4] Wei, R. B.; Liu, Y.; Liang, Y. Chin. J. Org. Chem. 2009, 29, 476(in Chinese). (魏荣宝, 刘洋, 梁娅, 有机化学, 2009, 29, 476.)
[5] Mertz, F. P.; Yao, R. C. Int. J. Syst. Bacteriol. 1990, 40, 34.
[6] Legocki, J.; Polec, I.; Zelechowski, K. Pestycydy 2010, 33, 59.
[7] Thompson, G. D.; Dutton, R.; Sparks, T. C. Pest. Manage. Sci. 2000, 56, 696.
[8] Tillman, P. G.; Mulrooney, J. E. J. Econ. Entomol. 2000, 93, 1638.
[9] Boeck, L. D.; Chio, E. H.; Eaton, T. E.; Godfrey, O. W.; Michel, K. H.; Nakatsukasa, W. M.; Yao, R. C. EP 0375316, 1990.
[10] Baker, P. J. US 5227295, 1993.
[11] Turner, J. R.; HuberM, L. B.; Broughton, M. C.; Mynderse, J. S.; Martin, J. W. US 5591606, 1997.
[12] Mynderse, J. S.; Baker, P. J.; Mabe, J. A.; Broughton, M. C.; Huber, M. B.; Martin, J. W.; Turner, J. R. WO 9420518, 1994.
[13] Bacci, L.; Lupi, D.; Savoldelli, S.; Rossaro, B. J. Entomol. Acarolog. Res. 20016, 48, 40.
[14] Salgado, V. L.; Sheets, J. J.; Watson, G. B.; Schmidt, A. L. Pestic. Biochem. Physiol. 1998, 60, 103.
[15] Carson, W.; Trumble, J. Arthropod Manage. Tests 1998, 23, 74.
[16] Kerns, D. Arthropod Manage. Tests 1996, 21, 117.
[17] Linduska, J. Arthropod Manage. Tests 1998, 23, 95.
[18] Thompson, G. D.; Sparks, T. C. Synthesis and Chemistry of Agrochemicals, American Chemical Society, Washington, DC, 2002, Chapter 5, pp. 61~73.
[19] Cleveland, C. B.; Mayes, M. A.; Cryer, S. A. Pest Manage. Sci. 2002, 58, 70.
[20] Chai, H. X.; Shi, D. X.; Zhang Q.; Li, J. R. Chem. Ind. Eng. Prog. 2011, 30, 239(in Chinese). (柴洪新, 史大昕, 张奇, 李加荣, 化工进展, 2011, 30, 239.)
[21] Sparks, T. C.; Dripps, J. E.; Watson, G. B.; Paroonagian, D. Pestic. Biochem. Physiol. 2012, 102, 1.
[22] Hong, L.; Zhao, Z. B.; Melançon, C. E.; Zhang, H.; Liu, H. W. J. Am. Chem. Soc. 2008, 130, 4954.
[23] Erb, A.; Weiss, H.; Härle, J.; Bechthold, A. Phytochemistry 2009, 70, 1812.
[24] Fisher, M. H. Phytochemicals for Pest Control, American Chemical Society, Washington, DC, 1997, Chapter 17, pp. 220~238.
[25] Sheehan, L. S.; Lill, S. R. E.; Wilkinson, B.; Sheridan, R. M.; Vousden, W. A.; Kaja, A. L.; Crouse, G. D.; Gifford, J.; Graupner, P. R.; Karr, L.; Lewer, P.; Sparks, T. C.; Leadlay, P. F.; Waldron, C.; Martin, C. J. J. Nat. Prod. 2006, 69, 1702.
[26] Creemer, L. C.; Kirst, H. A.; Paschal, J. W. J. Antibiot. 1998, 51, 795.
[27] Daeuble, J.; Sparks, T. C.; Johnson, P.; Graupner, P. R. Bioorg. Med. Chem. 2009, 17, 4197.
[28] Tietze, L. F.; Brasche, G.; Grube, A.; Böhnke, N.; Stadler, C. Chem.-Eur. J. 2007, 13, 8543.
[29] Oliver, M. P.; Crouse, G. D.; Demeter, D. A.; Sparks, T. C. J. Agric. Food Chem. 2015, 63, 5571.
[30] Shi, D. X.; Feng, X.; Zhuang, X. L.; Chai, H. X.; Liu, A. J.; Liu, T.; Zhang, Q.; Li, J. R. Chin. J. Org. Chem. 2014, 34, 2543(in Chinese). (史大昕, 冯雪, 庄晓磊, 柴洪新, 柳安军, 刘霆, 张奇, 李加荣, 有机化学, 2014, 34, 2543.)
[31] Calabrese, A. WO 2017040763, 2017.
[32] Cheng, L. X. Mod. Agrochem. 2004, 3, 7(in Chinese). (程隆新, 现代农药, 2004, 3, 7.)
[33] Thomas C. Pestic. Biochem. Physiol. 2000, 67, 187.
[34] Creemer L. C.; Kirst H. A.; Paschal J. W. J. Antibiot. 1998, 51, 795.
[35] Tian, X. L.; Yin, X. H.; Long, Y. H.; Li, M.; Cai, T.; Li, R. Y.; Zhu, L. H. Chin. J. Pestic Sci. 2016, 18, 589(in Chinese). (田雪莲, 尹显慧, 龙友华, 李明, 蔡滔, 李荣玉, 朱流红, 农药学学报, 2016, 18, 589.)
[36] Wu, Y. L.; Wu, W. L.; Yao, Z. J.; Li, Y. L.; Wang, Y. F.; Li, J. C.; Sun, X. L.; Peng, Z. H.; Yu, Q.; Hu, T. S.; Zeng, B. B.; Wang, X. Z. Chin. J. Org. Chem. 2001, 21, 1051(in Chinese). (吴毓林, 吴文连, 姚祝军, 黎运龙, 王燕芳, 李金翠, 孙小玲, 彭陟辉, 俞千, 胡泰山, 曾步兵, 王祥柱, 有机化学, 2001, 21, 1051.)
[37] Hua, N. Z. Agrochemicals 2015, 54, 1(in Chinese). (华乃震, 农药, 2015, 54, 1.)
[38] Zhang, K.; Liu, S. L.; Liu, A. J.; Chai, H. X.; Li, J. R.; A, L. M. S. Beilstein J. Org. Chem. 20017, 13, 2603.
[39] Bai, Y.; Shen, X.; Li, Y.; Dai, M. J. Am. Chem. Soc. 2016, 138, 10838.

多杀菌素A衍生物的合成及其生物活性研究

Study on the Synthesis and Insecticidal Activity of Spinosyn A Derivatives

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Weizhong Ding, Bingwen Zhang, Yanqing Xue, Yuqi Lin, Zhijun Tang, Jing Wang, Wenchao Yang, Xiaofeng Wang, Wen Liu. A New Polyketide from Fusarium graminearum [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3319-3322.
[2]	Xiurong Wu, Chaojiang Xiao, Yi Shen, Hongxia Tang, Junyi Zhu, Bei Jiang. Research Progress on Antimalarial Natural Sesquiterpenoids from Plants from 1972 to 2022 [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2764-2789.
[3]	Min Liu, Dongyan Yang, Yumei Xiao, Wangcang Su, Fenghai Zhao, Qin Zhaohai .. Synthesis and Bioactivities of 5-Nitroimino-[1,4-2H]-1,2,4-triazolines as Olefin-Imidacloprid Mimics [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2790-2799.
[4]	Zichan Zhang, Yang Sun, Sheng Hua, Baolin Xu, Min Zhang, Qin Zhao, Dandan Zheng, Yang Wang, Jianfeng Ju, Yujun Shi, Hong Dai. Synthesis and Insecticidal Activity of Novel Pyrazole Amides Containing an Isoxazole Moiety [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1435-1443.
[5]	Huaiyuan Zhang, Nuo Xu, Rongping Tang, Xingli Shi. Recent Advances in Asymmetric Dearomatization Reactions Induced by Chiral Hypervalent Iodine Reagents [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3784-3805.
[6]	Lei Wang, Shujing Yu, Na Yang, Baolei Wang. Studies on the Synthesis and Biological Activities of Novel Dihydroquinazolinone-Containing Caffeine Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 299-307.
[7]	Xiangkai Kong, Yipeng Zhang, Lingjing Dang, Wen Chen, Hongbin Zhang. Research Progress in Synthesis of Indole Alkaloids Vindoline and Vindorosine [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2728-2744.
[8]	Liangcai Yao, Jinghan Gui. Application of the Radical Polyene Cyclization Reaction in Natural Product Synthesis [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2703-2714.
[9]	Wenjuan Li, Rui Zhang, Zhihua Cai, Xiaoqiang Han, Lin He, Bin Dai. Constrution and Insecticidal Activities of Trifluoromethylated Benzocyclicsulfoximine Derivatives by [3+2] Cycloaddition Reaction of Beznyne [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2832-2839.
[10]	Ran Gao, Weisheng Tian. Synthesis of Azedarachol and 2α,3α,20R-Trihydroxypregnane-16β-methacrylate [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2521-2526.
[11]	Fasheng Shi, Shengwen Wang, Huan Xu, Xingxing Lu, Xinling Yang, Tengda Sun, Changkai Wang, Xiaoming Zhang, Qing Yang, Yun Ling. Design, Synthesis and Fungicidal Actiνity of Noνel Thiosemicarbazide Compounds [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2106-2116.
[12]	Yaqian Yan, Haoxin Wang, Yaoyao Li. Discovery of a New Polycyclic Tetramate Macrolactam 3-Hydroxycombamide I [J]. Chinese Journal of Organic Chemistry, 2022, 42(5): 1557-1561.
[13]	Jie Luo, Yaqian Yan, Haoxin Wang, Yaoyao Li. Discovery of a New Polycyclic Tetramate Macrolactam Clifednamide K [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1224-1228.
[14]	Mengmeng Xu, Quan Cai. Progress of Catalytic Asymmetric Diels-Alder Reactions of 2-Pyrones [J]. Chinese Journal of Organic Chemistry, 2022, 42(3): 698-713.
[15]	Shu Chen, Yingying Shao, Xinhao Fu, Qingwu Chen, Xiaohua Du, Chengxia Tan. Design, Synthesis and Insecticidal Activities of Pyridyl Thiazole Diamide Compounds [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3870-3879.