Synthesis and Insecticidal Activities of Novel Optically Active Dicarboxamides Containing N-Trifluoroacetyl Sulfulimiyl Substituents

doi:10.6023/cjoc202101032

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (9): 3532-3538.DOI: 10.6023/cjoc202101032 Previous Articles Next Articles

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新型含N-COCF₃硫亚胺取代的手性双酰胺类化合物的合成与生物活性研究

周莎^a^,^*(), 王目阔^b, 谢伟彬^a, 周沙^a, 熊丽霞^a, 赵毓^a^,^*(), 李正名^a^,^*()

a 南开大学化学学院元素有机化学国家重点实验室农药国家工程中心(天津) 天津 30071
b 南开大学药学院药物化学生物学重点实验室天津市药物分子研究重点实验室天津 300353

收稿日期:2021-01-19 修回日期:2021-05-09 发布日期:2021-07-19
通讯作者: 周莎, 赵毓, 李正名
作者简介:
† 共同第一作者.
基金资助:
国家重点研发计划(2018YFD0200100); 国家自然科学基金(21602118)

Synthesis and Insecticidal Activities of Novel Optically Active Dicarboxamides Containing N-Trifluoroacetyl Sulfulimiyl Substituents

Sha Zhou^a(), Mukuo Wang^b, Weibin Xie^a, Shaa Zhou^a, Lixia Xiong^a, Yu Zhao^a(), Zhengming Li^a()

a National Pesticidal Engineering Centre (Tianjin), State Key Laboratory of Elemento-organic Chemistry,College of Chemistry, Nankai University, Tianjin 300071
b State Key Laboratory of Medicinal Chemical Biology, Tianjin Key Laboratory of Molecular Drug Research, College of Pharmacy, Nankai University, Tianjin 300353

Received:2021-01-19 Revised:2021-05-09 Published:2021-07-19
Contact: Sha Zhou, Yu Zhao, Zhengming Li
About author:
† These authors contributed equally to this work.
Supported by:
National Key Research and Development Program of China(2018YFD0200100); National Natural Science Foundation of China(21602118)

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Abstract

Dicarboxamide is a class of special insecticide targeting at Ryanodine Receptor (RyR) with potent activity, new mode of action and eco-friendly characteristics in modern pest control. To explore new structures acting on RyR, a series of new dual chiral N-COCF₃ sulfiliminyl derivatives were designed, synthesized, and characterized by melting point, ¹H NMR, high-resolution mass spectrometry (HRMS) and optical polarimeter. Their insecticidal activity against oriental armyworm (Pseudaletia separata Walker) were evaluated and the structure-activity relationship were summarized. The bioactivity revealed that some compounds showed favourable insecticidal activities against oriental armyworm. The sequence of these isomers' insecticidal activity was (S_c,R_s)≥(S_c,S_s). It was worth noting that compounds containing 2-CH₃-4-Cl in the anilide moiety gave better activity than the compounds with 3-CF₃. The study provided some important information for the further research of sulfiliminyl dicarboxamides.

Key words: chirality, sulfilimine, bioactivity, ryanodine receptor, dicarboxamides

Cite this article

Sha Zhou, Mukuo Wang, Weibin Xie, Shaa Zhou, Lixia Xiong, Yu Zhao, Zhengming Li. Synthesis and Insecticidal Activities of Novel Optically Active Dicarboxamides Containing N-Trifluoroacetyl Sulfulimiyl Substituents[J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3532-3538.

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Fig. & Tab. 8

References 22

[1]	Sattelle, D. B.; Cordova, D.; Cheek, T. R. Invert Neurosci. 2008, 8, 107. doi: 10.1007/s10158-008-0076-4
[2]	Tohnishi, M.; Nakao, H.; Furuya, T.; Seo, A.; Kodama, H.; Tsubata, K.; Fujioka, S.; Hirooka, T.; Nishimatsu, T. J. Pestic. Sci. 2005, 30, 354.
[3]	Lahm, G. P.; Myers, B. J.; Selby, T. P.; Stevenson, T. M. WO 2001070671, 2001.
[4]	Selby, T. P.; Lahm, G. P.; Stevenson, T. M.; Hughes, K. A.; Cordova, D.; Annan, I. B.; Barry, J. D.; Benner, E, A.; Currie, M. J.; Pahutski, T. F. Bioorg. Med. Chem. Lett. 2013, 23, 6341. doi: 10.1016/j.bmcl.2013.09.076
[5]	Zhou, S.; Yan, T.; Li, Y. X.; Jia, Z. H.; Wang, B. L.; Zhao, Y.; Qiao, Y. Y.; Xiong, L. X.; Li, Y. Q.; Li, Z. M. Org. Biomol. Chem. 2014, 12, 6643. doi: 10.1039/c4ob00716f pmid: 25026986
[6]	Zhou, S.; Yan, T.; Zhou, S.; Hua, X. W.; Wang, B. L.; Gu, Y. C.; Xiong, L. X.; Li, Y. Q.; Li, Z. M. Chin. J. Chem. 2014, 32, 567. doi: 10.1002/cjoc.201400223
[7]	Zhou, S.; Jia, Z. H.; Xiong, L. X.; Yan, T.; Yang, N.; Wu, G. P.; Song, H. B.; Li, Z. M. J. Agric. Food Chem. 2014, 62, 6269.
[8]	Zhou, S.; Gu, Y. C.; Liu, M.; Wu, C. C.; Zhou, S.; Zhao, Y.; Jia, Z. H.; Wang, B. L.; Xiong, L. X.; Yang, N.; Li, Z. M. J. Agric. Food Chem. 2014, 62, 11054.
[9]	Zhou, S.; Li, Z. M. Receptor Clinical Investigation 2014, DOI: 10.14800/rci.339.
[10]	Zhou, S.; Li, Z. M. J. Phys. Chem. Biophys. 2014, 5, 174.
[11]	Zhou, S.; Zhang, X. L.; Wei, W.; Liu, J. B.; Xiong, L. X.; Yang, N.; Li, Z. M. Chin. J. Org. Chem. 2014, 34, 1424. (in Chinese). doi: 10.6023/cjoc201401023
	周莎, 张秀兰, 魏巍, 刘敬波, 熊丽霞, 杨娜, 李正名, 有机化学, 2014, 34, 1424).
[12]	Meng, X. D.; Zhou, S.; Xie, Y. T.; Zhao, Y.; Xiong, L. X.; Zhou, S.; Li, Z. M. Chin. J. Org. Chem. 2017, 37, 908. (in Chinese). doi: 10.6023/cjoc201610027
	( 孟祥德, 周沙, 解永涛, 赵毓, 熊丽霞, 周莎, 李正名, 有机化学, 2017, 37, 908.)
[13]	Zhou, S.; Zhou, S.; Xie, Y. T.; Jin, R. Y.; Meng, X. D.; Zhang, D. K.; Hua, X. W.; Liu, M.; Wu, C. C.; Xiong, L. X.; Zhao, Y.; Li, Z. M. Chin. Chem. Lett. 2017, 28, 1499. doi: 10.1016/j.cclet.2017.02.021
[14]	Zhou, S.; Meng, X. D.; Jin, R. Y.; Ma, Y.; Xie, Y. T.; Zhao, Y.; Song, H. J.; Xiong, L. X.; Li, Z. M. Mol. Diversity 2017, 21, 915. doi: 10.1007/s11030-017-9767-2
[15]	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. doi: 10.1016/j.ibmb.2017.11.009
[16]	Abbott, W. S. J. Econ. Entomol. 1925, 18, 265.
[17]	Raymond, M. Cah. ORSTOM Ser. Ent. Med. Parasitol. 1985, 23, 117.
[18]	Schrödinger, Release 2017-1: Protein Preparation Wizard, Schrödinger, LLC, New York, 2017.
[19]	Schrödinger, Release 2017-1: LigPrep; Schrödinger, LLC, New York, 2017.
[20]	Schrödinger, Release 2017-1: Epik; Schrödinger, LLC, New York, 2017.
[21]	Schrödinger, Release 2017-1: ConfGen; Schrödinger, LLC, New York, 2017.
[22]	Schrödinger, Release 2017-1: Glide; Schrödinger, LLC, New York, 2017.

Compd.	LC₅₀/(mg•L^–1)
Compd.	y=a+bx	R	LC₅₀	LC₉₅
Ia	y=0.2758+2.6470x	0.9726	60.9216	254.7882
Ib	y=–1.8087+2.6912x	0.9837	338.8469	1384.2087
If	y=–4.7357+3.9709x	0.9440	282.9624	734.4319
Ig	y=1.3515+3.8835x	0.9446	8.6994	23.0697
Ih	y=1.6886+2.0064x	0.9501	44.7156	295.3081
IIa	y=–3.7613+7.8288x	0.9950	13.1557	21.3412
IIg	y=–1.7923+6.0046x	0.9701	13.5261	25.4158
IIh	y=–1.4049+3.8814x	0.9676	44.6843	118.5586
Fluben- diamide	y=7.4237+2.6428x	0.9945	0.1230	0.5160

Compd.	LC₅₀/(mg•L^–1)
Compd.	y=a+bx	R	LC₅₀	LC₉₅
Ia	y=0.2758+2.6470x	0.9726	60.9216	254.7882
Ib	y=–1.8087+2.6912x	0.9837	338.8469	1384.2087
If	y=–4.7357+3.9709x	0.9440	282.9624	734.4319
Ig	y=1.3515+3.8835x	0.9446	8.6994	23.0697
Ih	y=1.6886+2.0064x	0.9501	44.7156	295.3081
IIa	y=–3.7613+7.8288x	0.9950	13.1557	21.3412
IIg	y=–1.7923+6.0046x	0.9701	13.5261	25.4158
IIh	y=–1.4049+3.8814x	0.9676	44.6843	118.5586
Fluben- diamide	y=7.4237+2.6428x	0.9945	0.1230	0.5160

Pocket	Docking score (kcal•mol^–1)	2D diagram
1	–3.54
2	–4.86

Pocket	Docking score (kcal•mol^–1)	2D diagram
1	–3.54
2	–4.86

Pocket	Docking score/ (kcal•mol^–1)	2D diagram
1	–3.89
2	–5.07

新型含N-COCF₃硫亚胺取代的手性双酰胺类化合物的合成与生物活性研究

Synthesis and Insecticidal Activities of Novel Optically Active Dicarboxamides Containing N-Trifluoroacetyl Sulfulimiyl Substituents

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References 22

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Compd.	Larvicidal activity (%) at conc. (mg•L^–1)
Compd.	200	100	50	25	10
Ia	100	60
Ib	30
Ic	100	60
Id	100	100	20	0
Ie	100	100	60	20
If	40
Ig	100	100	100	100	40
Ih	100	100	30
Ii	55
IIa	100	100	100	100	20
IIc	50
IId	40
IIe	100	100	40	0
IIf	40
IIg	100	100	100	100	25
IIh	100	100	60
Flubendiamide	100	100	100	100	100

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新型含N-COCF3硫亚胺取代的手性双酰胺类化合物的合成与生物活性研究

Synthesis and Insecticidal Activities of Novel Optically Active Dicarboxamides Containing N-Trifluoroacetyl Sulfulimiyl Substituents

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Abstract

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Fig. & Tab. 8

References 22

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新型含N-COCF₃硫亚胺取代的手性双酰胺类化合物的合成与生物活性研究