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

Xianhao Wang , Jianguo Li , Guangjian Wang , Xianzheng Han , Dongmei Li , Zhongzhen Tian

Chemical Research in Chinese Universities ›› 2019, Vol. 35 ›› Issue (5) : 799 -805.

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Chemical Research in Chinese Universities ›› 2019, Vol. 35 ›› Issue (5) : 799 -805. DOI: 10.1007/s40242-019-9122-5
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Design, Synthesis and Insecticidal Activities of Novel 5-Alkoxyfuran-2(5H)-one Derivatives

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Abstract

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.

Keywords

Butenolide derivative / Flupyradifurone / Neonicotinoid / Insecticidal activity

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Xianhao Wang, Jianguo Li, Guangjian Wang, Xianzheng Han, Dongmei Li, Zhongzhen Tian. Design, Synthesis and Insecticidal Activities of Novel 5-Alkoxyfuran-2(5H)-one Derivatives. Chemical Research in Chinese Universities, 2019, 35(5): 799-805 DOI:10.1007/s40242-019-9122-5

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References

[1]

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.

[2]

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

[3]

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

[4]

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

[5]

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

[6]

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

[7]

Fang T, Sun C W, Xu Y Y, Yuan J, Wang Y F, Xing J H. Chem. Res. Chinese Universities, 2014, 306: 931.

[8]

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

[9]

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

[10]

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

[11]

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

[12]

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

[13]

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

[14]

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.

[15]

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

[16]

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

[17]

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

[18]

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

[19]

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.

[20]

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.

[21]

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

[22]

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

[23]

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

[24]

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

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