Design, Synthesis and Insecticidal Activities of Novel 5-Alkoxyfuran-2(5H)-one Derivatives

Xianhao Wang1, Jianguo Li2, Guangjian Wang3, Xianzheng Han2, Dongmei Li1, Zhongzhen Tian1
1Shandong Provincial Key Laboratory of Fluorine Chemistry and Chemical Materials, School of Chemistry and Chemical Engineering, University of Jinan, Jinan, P. R. China
2Research and Development Center, Hailir Pesticides and Chemicals Group Co., Ltd., Qingdao, P. R. China
3State Key Laboratory Base for Eco-Chemical Engineering in College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao, P. R. China

Tóm tắt

A series of novel 5-alkoxyfuran-2(5H)-one derivatives was synthesized, and characterized by 1H NMR, 13C NMR and HRMS. Biological activities of all the title compounds were evaluated systematically. Preliminary bioassays indicated that most of the compounds exhibited moderate insecticidal activities against Aphis craccivora and Nilaparvata lugens at 100 mg/L. Compounds 4h and 4w exhibited 100% mortality rate against Aphis craccivora at 100 mg/L, and compound h exhibited good mortality rate against Aphis craccivora and Nilaparvata lugens (60% and 75%, respectively) even at 4 mg/L. The results demonstrated the impact of various chemical groups on insecticidal activities and provided a potential clue for further exploring novel high-effective broad-spectrum insecticides.

Từ khóa


Tài liệu tham khảo

Klein A. M., Vaissiere B. E., Cane J. H., Steffan-Dewenter I., Cunningham S. A., Kremen C., Tscharntke T., Proc. R. Soc. B, 2007, 274, 303

Aizen M. A., Harder L. D., Curr. Biol., 2009, 19, 915

Gallai N., Salles J. M., Settele J., Vaissiere B. E., Ecol. Econ., 2009, 68, 810

Aizen M. A., Garibaldi L. A., Cunningham S. A., Klein A. M., Curr. Biol., 2008, 18, 1572

Breeze T. D., Bailey A. P., Balcombe K. G., Potts S. G., Agric. Eco-syst. Environ., 2011, 142, 137

Cresswell J. E., Robert F. X. L., Florance H., Smirnoff N., Pest. Ma-nag. Sci., 2014, 70, 332

Fang T., Sun C. W., Xu Y. Y., Yuan J., Wang Y. F., Xing J. H., Chem. Res. Chinese Universities, 2014, 30(6), 931

Whitehorn P. R., O’Connor S., Wackers F. L., Goulson D., Science, 2012, 336, 351

Alkassab A. T., Kirchner W. H., Ecotoxicology, 2016, 25, 1000

Aliouane Y., Hassani A. K., Gary V., Armengaud C., Lambin M., Gauthier M., Environ. Toxicol. Chem., 2009, 28, 113

Hesselbach H., Scheiner R., Ecotoxicology, 2019, 28, 354

Campbell J. W., Cabrera A. R., Stanley-Stahr C., Ellis J. D., J. Econ. Entomol., 2016, 109, 1967

Hesselbach H., Scheiner R., Sci. Rep., 2018, 8, 4954

Nauen R., Jeschke P., Velten R., Beck M. E., Ebbinghaus-Kintscher U., Thielert W., Wölfel K., Haas M., Kunz K., Raupach G., Pest. Manag. Sci., 2015, 71, 850

Jeschke P., Nauen R., Gutbrod O., Beck M. E., Matthiesen S., Haas M., Velten R., Pestic. Biochem. Phys., 2015, 121, 31

Xiao H., Parkin K. L., Phytochemistry, 2007, 68, 1059

Xu X. Y., Zhang X. Y., He F., Peng J., Nong X. H., Qi S. H., Nat. Prod. Commun., 2013, 8, 1069

Seto Y., Kameoka H., Yamaguchi S., Kyozuka J., Plant. Cell. Phy-siol., 2012, 53, 1843

Lattmann E., Sattayasai N., Schwalbe C. S., Niamsanit S., Billington D. C., Lattmann P., Langley C. A., Singh H., Dunn S., Curr. Drug. Discov. Technol., 2006, 3, 125

Lu S. Y., Shao X. S., Li Z., Xu Z. P., Zhao S. H., Wu Y. L., Xu X. Y., J. Agric. Food. Chem., 2012, 60, 322

Lizos D., Weiler S., Stiefl N. J., Organic Compounds, WO 2009013335, 2009

Byczek-Wyrostek A., Kitel R., Rumak K., Skonieczna M., Kasprzycka A., Walczak K., Eur. J. Med. Chem., 2018, 150, 687

Tian Z. Z., Shao X. S., Li Z., Qian X. H., Huang Q. C., J. Agric. Food. Chem., 2007, 55, 2288

Zhang D. D., Cui, S. X., Xu Z. P., Li D. M., Tian Z. Z., Chin. Chem. Lett., 2017, 28, 1743