Targeted Synthesis of Anthranilic Diamides Insecticides Containing Trifluoroethoxyl Phenylpyrazole

doi:10.1007/s40242-020-0287-8

高等学校化学研究 ›› 2021, Vol. 37 ›› Issue (3): 655-661.doi: 10.1007/s40242-020-0287-8

Targeted Synthesis of Anthranilic Diamides Insecticides Containing Trifluoroethoxyl Phenylpyrazole

LI Huangong, ZHAO Yangyang, SUN Pengwei, GAO Li, XIONG Lixia, YANG Na, ZHOU Sha, LI Yuxin, LI Zhengming

State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, P. R. China

收稿日期:2020-09-17 修回日期:2020-11-07 出版日期:2021-06-01 发布日期:2020-11-09
通讯作者: LI Zhengming, LI Yuxin E-mail:nkzml@vip.163.com;liyx128@nankai.edu.cn
基金资助:
This work was supported by the National Key Research and Development Program of China(Nos.2018YFD0200100, 2017YFD0200505) and the National Na-tural Science Foundation of China(Nos.31972287, 21602118).

Targeted Synthesis of Anthranilic Diamides Insecticides Containing Trifluoroethoxyl Phenylpyrazole

LI Huangong, ZHAO Yangyang, SUN Pengwei, GAO Li, XIONG Lixia, YANG Na, ZHOU Sha, LI Yuxin, LI Zhengming

State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, P. R. China

Received:2020-09-17 Revised:2020-11-07 Online:2021-06-01 Published:2020-11-09
Contact: LI Zhengming, LI Yuxin E-mail:nkzml@vip.163.com;liyx128@nankai.edu.cn
Supported by:
This work was supported by the National Key Research and Development Program of China(Nos.2018YFD0200100, 2017YFD0200505) and the National Na-tural Science Foundation of China(Nos.31972287, 21602118).

摘要/Abstract

摘要： Aseries of novel anthranilic diamides analogues(9a-9t) containing trifluoroethoxyl pyrazole moiety was designed and synthesized and their insecticidal bioactivities against Mythimna separata(Walker, M. separata) and Plutellaxylostella (P. xylostella) were evaluated. The structures of the title compounds were confirmed by ¹H NMR, ¹³C NMR and HRMS. Preliminary insecticidal activities showed that some of the title compounds possessed good to excellent bioactivities towards M. separata and P. xylostella. Compounds 9c and 9t exhibited 100% mortality rate against M. separate at 0.2 mg/L. For the P. xylostella, the synthesized compounds(9c-9e, 9i and 9o) showed 70%, 80%, 75%, 65% and 60% insecticidal activities at 1×10^-6 mg/L, respectively, higher than that of chlorantraniliprole(0). Based on excellent insecticidal activities, the mode of the action was tested by the calcium-imaging technique, the results of which demonstrated that the novel compounds shared the same target with chlorantraniliprole. The binding pose of the most active compound 9t in RyRs of P. xylostella was predicted by molecular docking, which showed that compound 9t interacted with the residues Glu140(A) and His147(A) via hydrogen bond.

关键词: Trifluoroethoxylphenylpyrazole, Anthranilic diamide derivative, Insecticidal bioactivity, Mode of the action, Molecular docking

Abstract: Aseries of novel anthranilic diamides analogues(9a-9t) containing trifluoroethoxyl pyrazole moiety was designed and synthesized and their insecticidal bioactivities against Mythimna separata(Walker, M. separata) and Plutellaxylostella (P. xylostella) were evaluated. The structures of the title compounds were confirmed by ¹H NMR, ¹³C NMR and HRMS. Preliminary insecticidal activities showed that some of the title compounds possessed good to excellent bioactivities towards M. separata and P. xylostella. Compounds 9c and 9t exhibited 100% mortality rate against M. separate at 0.2 mg/L. For the P. xylostella, the synthesized compounds(9c-9e, 9i and 9o) showed 70%, 80%, 75%, 65% and 60% insecticidal activities at 1×10^-6 mg/L, respectively, higher than that of chlorantraniliprole(0). Based on excellent insecticidal activities, the mode of the action was tested by the calcium-imaging technique, the results of which demonstrated that the novel compounds shared the same target with chlorantraniliprole. The binding pose of the most active compound 9t in RyRs of P. xylostella was predicted by molecular docking, which showed that compound 9t interacted with the residues Glu140(A) and His147(A) via hydrogen bond.

Key words: Trifluoroethoxylphenylpyrazole, Anthranilic diamide derivative, Insecticidal bioactivity, Mode of the action, Molecular docking

LI Huangong, ZHAO Yangyang, SUN Pengwei, GAO Li, XIONG Lixia, YANG Na, ZHOU Sha, LI Yuxin, LI Zhengming. Targeted Synthesis of Anthranilic Diamides Insecticides Containing Trifluoroethoxyl Phenylpyrazole[J]. 高等学校化学研究, 2021, 37(3): 655-661.

参考文献 35

[1]	Jeanguenat A., Pest Manage. Sci., 2013, 22, 7
[2]	Lahm G. P., Selby T. P., Freudenberger J. H., Stevenson T. M., Mers B. J., Seburyamo G., Smith B. K., Flexner L., Clark C. E., Cordova D., Bioorg. Med. Chem. Lett., 2005, 15, 4898
[3]	Tohnishi M., Nishimatsu T., Motoba K., Hirooka T., Seo A., J. Pestic. Sci., 2010, 35, 490
[4]	Lahm G. P., Stevenson T. M., Selby T. P., Freudenberger J. H., Cordova D., Flexner D. L., Bellin C. A., Dubas C. M., Smith B. K., Hughes K. A., Hollingshaus J. G., Clark C. E., Benner E. A., Bioorg. Med. Chem., 2007, 17, 6274
[5]	Chai B. S., He X. M., Wang J. F., Li Z. N., Liu C. L., Agrochemicals, 2006, 49, 167
[6]	Li B., Yang H. B., Wang J. F., Song Y. Q., Modern Agrochemicals, 2014, 3, 17
[7]	Koyanagi T., Morita M., Nakamoto K., Hisamatsu A., Preparation of Anthranilamides as Pesticides, WO2005077934, 2005
[8]	Koyanagi T., Nakamoto K., Method for Preparing Halopyrazole Moiety-containing Anthranilamides, WO2008155990, 2008
[9]	Roditakis E., Steinbach D., Moritz G., Vasakis F., Stavrakaki M., Ilias A., García-Vidal L., Martínez-Aguirre M. R., Bielza P., Morou E., Silva J. E., Silva W. M., Siqueira H. A., Iqbal S., Troczka B. J., Williamson M. S., Bass C., Tsagkarakou A., Vontas J., Nauen R., Insect Biochem. Mol. Biol., 2017, 80, 11
[10]	Yao R., Zhao D. D., Zhang S., Zhou L. Q., Wang X., Gao C. F., Wu S. F., Pest Manage. Sci., 2017, 63, 1169
[11]	Wang B. L., Zhu H. W., Li Z. M., Zhang X., Yu S. J., Ma Y., Song H. B., Pest Manage. Sci., 2019, 75, 3273
[12]	Liu J. B., Li Y. X., Zhang X. L., Hua X. W., Wu C. C., Wei W., Wan Y. Y., Cheng D. D., Xiong L. X., Yang N., Song H. B., Li Z. M., J. Agric. Food Chem., 2016, 64, 3697
[13]	Liu Q., Zhu R., Gao S., Ma S. H., Tang H. J., Yang J. J., Diao Y. M., Wang H. L., Zhu H. J., Pest Manage. Sci., 2017, 73, 917
[14]	Shi J. J., Ren G. H., Wu N. J., Weng J. Q., Xu T. M., Liu X. H., Tan C. X., Chin. Chem. Lett., 2017, 28, 1727
[15]	Mao M. Z., Li Y. X., Zhou Y. Y., Zhang X. L., Liu Q. X., Di F. J., Song H. B., Xiong L. X., Li Y. Q., Li Z. M., J. Agric. Food Chem., 2014, 62, 1536
[16]	Zhou S., Zhou S., Xie Y. T., Meng X. D., Wang B. L., Xiong L. X., Yang N., Li Z. M., Chin. Chem. Lett., 2018, 29, 1254
[17]	Liu J. B., Li F. Y., Dong J. Y., Li Y. X., Zhang X. L., Wang Y. H., Xiong L. X., Li Z. M., Bioorg. Med. Chem., 2018, 26, 3541
[18]	Liu J. B., Li Y. X., Zhang X. L., Cheng D. D., Wei W., Wu C. C., Xie Y. T., Xiong L. X., Li Z. M., Chin. J. Chem., 2017, 35, 368
[19]	Hagmann W. K., J. Med. Chem., 2008, 51, 4359
[20]	Gouverneur V., Müller K., Fluorine in Pharmaceutical and Medicinal Chemistry, Imperial College Press, London, 2012
[21]	Gillis E. P., Eastman K. J., Hill M. D., Donnelly D. J., Meanwell N. A., J. Med. Chem., 2015, 58, 8315
[22]	Nohara A., Maky Y., Pyridyl Methylsulfinyl Benzimidazole Derivatives, US4727150A, 1988
[23]	Hua N. Z., Modern Agrochemicals, 2015, 35, 7
[24]	Zhao Y., Li Y. Q., Xiong L. X., Wang H. X., Li Z. M., Chin. J. Chem., 2012, 30, 1748
[25]	Zhang J. F., Xu J. Y., Wang B. L., Li Y. X., Xiong L. X., Li Y. Q., Ma Y., Li Z. M., J. Agric. Food Chem., 2012, 60, 7565
[26]	Fumiyuki S., Hidenori A., Natsuko K., Kazuo O., Katsuya N., Preparation of Pyrazole Derivatives Useful as COX-1 Inhibitors, US20040116475, 2004
[27]	Abbott W. S., J. Econ. Entomol., 1925, 18, 265
[28]	Wu Y. D., Shen J. L., Chen J., Li X. W., Li A. M., Plant Protection, 1996, 22, 3
[29]	Ma H., Wang K. Y., Xia X. M., Zhang Y., Guo Q. L., Modern Agrochemicals, 2006, 5, 44
[30]	Takahashi A., Camacho P., Lechleiter J. D., Herman B., Physiol. Rev., 1999, 79, 1089
[31]	Morris G. M., Huey R., Lindstrom W., Sanner M. F., Belew R. K., Goodsell D. S., Olson A. J., J. Comput. Chem., 2009, 30, 2785
[32]	Lin L. Y., Liu C., Qin J., Wang J., Dong S. J., Chen W., He W. Y., Gao Q. Z., You M. S., Yuchi Z. G., Insect Biochem. Mol. Biol., 2017, 92, 73
[33]	David B. S., Daniel C., Timothy R. C., Invertebr. Neurosci., 2008, 8, 107
[34]	Yu G., Luo L. J., Chen S. H., He F., Xie Y., Luo D. X., Xue W., Wu J., Chemistry Select, 2018, 3, 10991
[35]	Luo D. X., Guo S. X., He F., Wang H. Y., Xu F. Z., Dai A., Zhang R. F., Wu J., Bioorg. Med. Chem. Lett., 2020, 30, 126902

Targeted Synthesis of Anthranilic Diamides Insecticides Containing Trifluoroethoxyl Phenylpyrazole

Targeted Synthesis of Anthranilic Diamides Insecticides Containing Trifluoroethoxyl Phenylpyrazole

可视化

摘要/Abstract

引用本文

使用本文

参考文献 35

相关文章 15

编辑推荐

Metrics

本文评价

[1]	Ghadah F. ALJOHANI, Fatma A. A. EL-HAG, Mohamed S. BEKHEIT, Ewies F. EWIES, May A. EL-MANAWATY. An Efficient One-pot Synthesis of Certain Stereoselective Spiro[pyrazole-4,5'-isoxazoline]-5-one Derivatives: In vitro Evaluation of Antitumor Activities,Molecular Docking and In silico ADME Predictions[J]. 高等学校化学研究, 2022, 38(4): 1073-1082.
[2]	QUAN Jishun, ZHANG Dongping, ZHANG Zhuo, WANG Jian, MA Chao, CHENG Maosheng. Design, Synthesis and Biological Evaluation of Pyrrolo[2,1-c] [1,4]benzodiazepine-3,11-dione Derivatives as Novel Neuroprotective Agents[J]. 高等学校化学研究, 2021, 37(3): 647-654.
[3]	CHEN Aiyu, LIANG Yongdong, YE Jiao, HU Aixi, LIAN Wenwen, LIU Ailin, DU Guanhua. Synthesis of Chalcone Derivatives Containing Furan or/and Pyran Ring as Neuraminidase Inhibitors[J]. 高等学校化学研究, 2019, 35(3): 395-402.
[4]	LIU Sicheng, SUN Shijun. Combined QSAR/QSPR, Molecular Docking, and Molecular Dynamics Study of Environmentally Friendly PBDEs with Improved Insulating Properties[J]. 高等学校化学研究, 2019, 35(3): 478-484.
[5]	MA Junjie, HUANG Kun, NI Xin, CHEN Roufen, XU Boxuan, WANG Cuifang. Design, Synthesis, Biological Activity and Molecular Docking Study of Coumarin Derivatives Bearing 2-Methyl b iphenyl Moiety[J]. 高等学校化学研究, 2019, 35(3): 410-417.
[6]	ZHAO Xiaohui, QIU Youli, JIANG Long, LI Yu. Analysis of Affinity Energy Between Biphenyl Dioxygenase and Polychlorinated Biphenyls Using Molecular Docking[J]. 高等学校化学研究, 2019, 35(2): 325-332.
[7]	JIN Bo, TAO Ye, YANG Hongliang. Synthesis, Biological Evaluation and Molecular Docking of Novel Phenylpyrimidine Derivatives as Potential Anticancer Agents[J]. 高等学校化学研究, 2018, 34(6): 912-917.
[8]	HE Wei, ZHAO Anran, ZOU Jiajia, LUO Xuan, LIN Xiao, WANG Lisheng, LIN Cuiwu. Synthesis, In vitro Coagulation Activities and Molecular Docking Studies on Three L-Histidine Amide Derivatives[J]. 高等学校化学研究, 2018, 34(1): 90-94.
[9]	LIANG Guangping, CHUNG Tseyu, GUO Jinhua, ZHANG Rongrong, XÜ Wei, TZEN Jason T. C., JIANG Renwang. Novel Cinobufagin Oxime Ether Derivatives as Potential Na⁺/K⁺-ATPase Inhibitors: Synthesis, Biological Screening and Molecular Docking[J]. 高等学校化学研究, 2017, 33(3): 378-383.
[10]	LI Xu, LI Chuanhua, JIANG Jianhong, GU Huiwen, WEI Deliang, YE Lijuan, HU Jilin, XIAO Shengxiong, ZHANG Hui, LI Xia, LI Qiangguo. Fluorescence Spectroscopic Studies on the Interaction Between a New Bismuth(III) Schiff Base Complex and Bovine Serum Albumin[J]. 高等学校化学研究, 2017, 33(2): 166-171.
[11]	YANG Haoran, REN Yujie, GAO Xiaodong, GAO Yonghong. Synthesis and Anticoagulant Bioactivity Evaluation of 1, 2, 5-Trisubstituted Benzimidazole Fluorinated Derivatives[J]. 高等学校化学研究, 2016, 32(6): 973-978.
[12]	FANG Ting, SUN Chuanwen, XU Yiyi, YUAN Jing, WANG Yuanfeng, XING Jiahua. Synthesis, Insecticidal Activities and Molecular Docking Studies on cis-Nitenpyram Analogues with a Flexible Amido Segment Anchored on Tetrahydropyrimidine Ring[J]. 高等学校化学研究, 2014, 30(6): 931-936.
[13]	ZHANG Xiaoyi, DENG Dongjie, TAN Jianjun, HE Yu, LI Chunhua, WANG Cunxin. Pharmacophore and Docking-based 3D-QSAR Studies on HIV-1 Integrase Inhibitors[J]. 高等学校化学研究, 2014, 30(2): 297-305.
[14]	PARVEEN Mehtab, MALLA Ali Mohammed, ALI Akhtar, ALAM Mahboob, MUSTAFA Mir Faisal. Silica-supported Thionyl Chloride-assisted Synthesis and Bioassay of Novel Tetrazinan-3-thione and 3-Oxo-pyrazolidine-4-carbonitrile Derivatives of Steroids[J]. 高等学校化学研究, 2014, 30(1): 55-62.
[15]	ZHU Qian-kun, ZHU Meng-li, ZOU Jia-xin, FENG Pei-chun, FAN Gao-tao, LIU Zu-bi, WANG Wan-jun. Molecular Modeling and Docking of Mannose-binding Lectin from Lycoris radiata[J]. 高等学校化学研究, 2013, 29(6): 1153-1158.