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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 8: 2547 - 2554

DOI: https://doi.org/10.6023/cjoc202004050

Synthesis and Unexpected Insecticidal Activity of (E)-3-(1-Imino-ethyl)-5,5-disubstituted-4-(methylamino)furan-2(5H)-one

  • Zhao Yu ,
  • Liu Xinlei ,
  • Li Yihao ,
  • Xu Leichuan ,
  • Su Yanhao ,
  • Jiang Jiazhen ,
  • Wang Ming'an
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  • Innovation Center of Pesticide Research, Department of Applied Chemistry, China Agricultural University, Beijing 100193

Received date: 2020-04-29

  Revised date: 2020-05-10

  Online published: 2020-05-29

Supported by

Project supported by the National Natural Science Foundation of China (No. 21772229).

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Abstract

In order to improve the fungicidal activity against phytopathogens and enlarge the constructed molecular library, eighteen novel (E)-3-(1-iminoethyl)-5,5-disubstituted-4-(methylamino)-furan-2(5H)-ones were designed and synthesized based on the diversity-oriented synthesis strategy when the C-4 phenyl group of 3-(1-iminoethyl)-5,5-disubstituted-4-phenylfuran-2(5H)-one was replaced with the methylamino group. Their structures were characterized by 1H NMR, 13C NMR, HR-MS spectral data. The crystal structure of (E)-3-(1-((4-methoxybenzyloxy)imino)ethyl)-4-(methylamino)-1-oxaspiro[4.5]dec-3-en-2-one (5O) was determined by X-ray diffraction analysis. The bioassay results indicated that all compounds did not exhibit significant in vivo fungicidal activities against phytopathogens, but some of them showed good insecticidal activities against Plutella xylostella, Mythimna seprata and Myzus persicae with 100% mortality at the concentration of 600 μg/mL.

Key words： (E)-3-(1-iminoethyl)-5,5-disubstituted-4-(methylamino)furan-2(5H)-one; diversity-oriented synthesis; oxime ether scaffold; insecticidal activity

Cite this article

Zhao Yu , Liu Xinlei , Li Yihao , Xu Leichuan , Su Yanhao , Jiang Jiazhen , Wang Ming'an . Synthesis and Unexpected Insecticidal Activity of (E)-3-(1-Imino-ethyl)-5,5-disubstituted-4-(methylamino)furan-2(5H)-one[J]. Chinese Journal of Organic Chemistry, 2020 , 40(8) : 2547 -2554 . DOI: 10.6023/cjoc202004050

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