Synthesis, insecticidal activities and DFT study of pyrimidin-4-amine derivatives containing the 1,2,4-oxadiazole motif

doi:10.1007/s11705-021-2091-5

Front. Chem. Sci. Eng.

2022, Vol. 16

Issue (7) : 1090-1100 https://doi.org/10.1007/s11705-021-2091-5

RESEARCH ARTICLE

Synthesis, insecticidal activities and DFT study of pyrimidin-4-amine derivatives containing the 1,2,4-oxadiazole motif

Yong-Hui Wen^1,², Long Cheng^1,², Tian-Ming Xu², Xing-Hai Liu¹(

), Ning-Jie Wu²(

)

¹. College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014, China
². Zhejiang Base of National Southern Pesticide Research Centre, Zhejiang Research Institute of Chemical Industry, Hangzhou 310023, China

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Abstract

Twenty six novel pyrimidin-4-amine derivatives containing the 1,2,4-oxadiazole motif were synthesized. Their chemical structures were confirmed by ¹H nuclear magnetic resonance (NMR), ¹³C NMR, and high-resolution mass spectrography. The insecticidal activity results indicated that some of them possessed excellent insecticidal activity (100%) against Mythimna separate, especially for compounds 6d, 6f, 6o, 6w, 6y and 6z. These compounds exhibited no activity against the insects Aphis medicagini and Tetranychus cinnabarinus. The structure- insecticidal activity relationships are discussed. Density functional theory analysis can potentially be used to design more active compounds. These results provide useful insecticide design information for further optimization.

Keywords synthesis pyrimidin-4-amine derivatives 1,2,4-oxadiazole insecticidal activity structure-activity relationship

Corresponding Author(s): Xing-Hai Liu,Ning-Jie Wu

Online First Date: 04 November 2021 Issue Date: 15 July 2022

Cite this article:

Yong-Hui Wen,Long Cheng,Tian-Ming Xu, et al. Synthesis, insecticidal activities and DFT study of pyrimidin-4-amine derivatives containing the 1,2,4-oxadiazole motif[J]. Front. Chem. Sci. Eng., 2022, 16(7): 1090-1100.

URL:

https://academic.hep.com.cn/fcse/EN/10.1007/s11705-021-2091-5
https://academic.hep.com.cn/fcse/EN/Y2022/V16/I7/1090

Fig.1 The design strategy of new pyrimidinamine derivatives.

Scheme 1 The synthesis of key pyrimidine intermediates e1–e8.

Scheme 2 The synthetic route of title pyrimidinamine compounds.

Tab.1 The insecticidal activity of synthesized compounds against three insects (mg?L^–1)

Fig.2 The intramolecular hydrogen bonds between the NH and halogen atoms of 6d.

Tab.2 Total energy and frontier orbital energy of flufenerim and 6d

Fig.3 The HOMO and LUMO of 6d and flufenerim.

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