Design and Synthesis of Novel meta-Diamide Compounds Containing Sulfur Derivatives as Potential Pesticides

Yan Zhang; Peixuan Li; Jingwen Wu; Yunyi Tan; Sha Zhou; Jifen Wang

doi:10.54647/chemistry150376

ISSN: 2995-6943

Volume 9, Number 2 (2024)

Year Launched: 2016

Journal Menu

■ About The Journal

■ Aims & Scope

■ Editorial Board

■ Article Processing Charge

■ Archive

Previous Issues

■ Volume 9, Number 2 (2024)

■ Volume 9, Number 1 (2024)

■ Volume 8, Number 3 (2023)

■ Volume 8, Number 2 (2023)

■ Volume 8, Number 1 (2023)

■ Volume 7, Number 3 (2022)

■ Volume 7, Number 2 (2022)

■ Volume 7, Number 1 (2022)

■ Volume 6, Number 2 (2021)

■ Volume 6, Number 1 (2021)

■ Volume 5, Number 4 (2020)

■ Volume 5, Number 3 (2020)

■ Volume 5, Number 2 (2020)

■ Volume 5, Number 1 (2020)

■ Volume 4, Number 5 (2019)

■ Volume 4, Number 4 (2019)

■ Volume 4, Number 3 (2019)

■ Volume 4, Number 2 (2019)

■ Volume 4, Number 1 (2019)

■ Volume 3, Number 3 (2018)

■ Volume 3, Number 2 (2018)

■ Volume 3, Number 1 (2018)

■ Volume 2, Number 3 (2017)

■ Volume 2, Number 2 (2017)

■ Volume 2, Number 1 (2017)

■ Volume 1, Number 2 (2016)

■ Volume 1, Number 1 (2016)

Design and Synthesis of Novel meta-Diamide Compounds Containing Sulfur Derivatives as Potential Pesticides

Volume 9, Issue 2, April 2024 | PP. 30-43 | PDF (477 K) | Pub. Date: September 19, 2024
DOI: 10.54647/chemistry150376 32 Downloads 1856 Views

Author(s)

Yan Zhang, School of Resources and Environmental Engineering, Shanghai Polytechnic University, Shanghai 201209, China

Peixuan Li, School of Resources and Environmental Engineering, Shanghai Polytechnic University, Shanghai 201209, China

Jingwen Wu, School of Resources and Environmental Engineering, Shanghai Polytechnic University, Shanghai 201209, China

Yunyi Tan, School of Resources and Environmental Engineering, Shanghai Polytechnic University, Shanghai 201209, China

Sha Zhou, Zhejiang A&F University, Zhejiang 310000, China

Jifen Wang, School of Resources and Environmental Engineering, Shanghai Polytechnic University, Shanghai 201209, China

Abstract
As a typical meta-Diamide (m-diamide) insecticide, Broflanilide is highly effective, exhibits low toxicity, and shows no cross resistance with traditional insecticides that act on the γ-aminobutyric acid (GABA) receptor. As a high halogen content potentially causes risks and was concerning to researchers, easily derivatized sulfur with diverse biological activities was introduced into leading compound based on the principles of the molecular drug design. Fifteen novel sulfur-containing m-amide derivatives, A-F, were synthesized through a series of experiments, and the structures were confirmed by melting point determinations, ¹H NMR, ¹³C NMR and HRMS. The biochemical properties of the compounds were closely related to their structural characteristics. However, the insecticidal activities of the target compounds were lower than expected. Structure-activity relationship (SAR) results revealed that the compounds R₁ = CN exhibited better insecticidal activity (D-3, 46.67%; E-3, 50.00%; and F-3, 34.48%) than that of other compounds against Plutella xylostella (P. xylostella) at 500 mg·L^-1. These experiments provide a reference for related research on the synthesis and derivatization of sulfur-containing compounds.

Keywords
m-diamine, sulfur, design, synthesis, insecticidal activity

Cite this paper
Yan Zhang, Peixuan Li, Jingwen Wu, Yunyi Tan, Sha Zhou, Jifen Wang, Design and Synthesis of Novel meta-Diamide Compounds Containing Sulfur Derivatives as Potential Pesticides , SCIREA Journal of Chemistry. Volume 9, Issue 2, April 2024 | PP. 30-43. 10.54647/chemistry150376

References

[ 1 ]	Du, S., Hu, X., J. Agric. Food Chem., 2023, vol. 71, p. 3620. https://doi.org/10.1021/acs.jafc.2c08414
[ 2 ]	Lahm, G.P., Cordova, D., Barry, J.D., Bioorg. Med. Chem., 2009, vol. 17, p. 4127. https://doi.org/10.1016/j.bmc.2009.01.018
[ 3 ]	Gao, Y., Zhang, Y., Wu, F., et al., J. Agric. Food Chem., 2020, vol. 68, p. 14768. https://doi.org/10.1021/acs.jafc.0c05728
[ 4 ]	Casida, J.E., Chem. Res. Toxicol., 2015, vol. 28, p. 560. https://doi.org/10.1021/tx500520w
[ 5 ]	Nakao, T., and Banba, S., Bioorg. Med. Chem., 2016, vol. 24, p. 372. https://doi.org/10.1016/j.bmc.2015.08.008
[ 6 ]	Luo, C., Xu, Q., Huang, C., et al., Org. Process Res. Dev., 2020, vol. 24, p. 1024. https://doi.org/10.1021/acs.oprd.0c00028
[ 7 ]	Liang, L., Wu, M., Huang, P., et al., J. Braz. Chem. Soc, 2024, vol. 35, p. 1. https://dx.doi.org/10.21577/0103-5053.20230111
[ 8 ]	Devendar, P., and Yang, G.F., Top. Curr. Chem. (Cham), 2017, vol. 375, p. 82. https://doi.org/10.1007/s41061-017-0169-9
[ 9 ]	Ando, W., Sulfur. Rep., 1981, vol. 1, p. 147. https://doi.org/10.1080/17415998109408001
[ 10 ]	Liang, S., Hofman, K., Friedrich, M., et al., ChemSusChem, 2021, vol. 14, p. 4878. https://doi.org/10.1002/cssc.202101635
[ 11 ]	Long, H., Wu, D., Wang, J., et al., Tetrahedron Lett., 2023, vol. 118, p. 154388. https://doi.org/10.1016/j.tetlet.2023.154388
[ 12 ]	Yoshida, K., Kobayashi, Y., Nomura, M., et al., World intellectual property organization, 2006137395 A1, 2006. 12. 28.
[ 13 ]	Hirabayashi, A., Banba, S., Wakita, T., et al., Japan patent application, 2011063549 A, 2011. 03. 31.
[ 14 ]	Huang, P.M., Wu, M.H., Lv, L., et al., Tetrahedron Lett., 2022, vol. 96, p. 153743. https://doi.org/10.1016/j.tetlet.2022.153743
[ 15 ]	Wang, J., Qin, S., Sheng, Z., et al., Mod. Agrochem, 2020, vol. 19, p. 20. https://doi.org/10.3969/j.issn.1671-5284.2020.03.004
[ 16 ]	Goergens, U., Yanagi, A., Wada, K., et al., 2009, vol. 11. World intellectual property organization, 2009080203 A2, 2009. 11. 05.
[ 17 ]	Zhang, Y., Li, Y., Li, H., et al., Chin. Chem. Lett., 2022, vol. 33, p. 501. https://doi.org/10.1016/j.cclet.2021.05.027
[ 18 ]	Nugent, B.M., Buysse, A.M., Loso, M.R., et al., Pest Manag. Sci., 2015, vol. 71, p. 928. https://doi.org/10.1002/ps.3865
[ 19 ]	Zhang, S., Zhang, X., Shen, J., et al., Pestic. Biochem. Physiol., 2017, vol. 140, p. 85. https://doi.org/10.1016/j.pestbp.2017.06.011