Synthesis and Biological Activity of Novel 1,4-Pentadien-3-one Oxime Esters Bearing Heterocycle Moiety

doi:10.11944/j.issn.1000-0518.2017.03.160219

Chinese Journal of Applied Chemistry ›› 2017, Vol. 34 ›› Issue (3): 316-323.DOI: 10.11944/j.issn.1000-0518.2017.03.160219

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Synthesis and Biological Activity of Novel 1,4-Pentadien-3-one Oxime Esters Bearing Heterocycle Moiety

XIA Lijuan^a^b,‡,WANG Xiaobin^a,‡,XIE Yan^a,WANG Xiaoyan^c,XIAO Wei^a,ZHONG Xinming^a,HUANG Minguo^a,XUE Wei^a^*()

^aState Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering,Key Laboratory of Green Pesticide and Agricultural Bioengineering,Ministry of Education,Certer for Rearch and Development of Fine Chemicals,Guizhou University,Guiyang 550025,China
^bEnvironmental Monitoring Station of Anshun,Anshun,Guizhou 561000,China
^cthe First Clinical Medical College,Nanjing University of Chinese Medicine,Nanjing 210029,China

Received:2016-05-25 Accepted:2016-08-09 Published:2017-02-27 Online:2017-02-27
Contact: XUE Wei
Supported by:
Supported by the National Natural Science Foundation of China(No.21462012), the Special Fund for Outstanding Scientific and Technological Candidates of Guizhou Province(No.201535), the Innovation Fund for Graduate Student of Guizhou University(No.2016076)

Abstract

Abstract:

In order to explore novel green pesticide with potent biological activities, a series of novel 1,4-pentadien-3-one oxime ester derivatives bearing heterocycle moiety, derived from curcumin, was designed and synthesized. Their structures were confirmed by infrared spectroscopy, proton nuclear magnetic resonance spectroscopy(¹H NMR), ¹³C NMR, and high resolution mass spectroscopy(HRMS). The bioassays indicate that inhibition rates of compound 5d against G.zeae, F.ox-ysporum and C.mandshurica at 50 mg/L are 64.75%, 52.05% and 69.68%, respectively, and compounds 5d, 5e and 5f have good curative and deactivation activities against tobacco mosaic virus at 500 mg/L, with the inhibition rates of 56.93% and 86.89%, 53.08% and 83.51%, and 53.40% and 89.01%, respectively. These indicate that 1,4-pentadien-3-one oxime ester is a valuable scafford to develope new compounds poessessing high biological activities such as potential antifungal and antiviral activities.

Key words: pentadien-one, oxime ester, fungicidal activities, antiviral activities

XIA Lijuan, WANG Xiaobin, XIE Yan, WANG Xiaoyan, XIAO Wei, ZHONG Xinming, HUANG Minguo, XUE Wei. Synthesis and Biological Activity of Novel 1,4-Pentadien-3-one Oxime Esters Bearing Heterocycle Moiety[J]. Chinese Journal of Applied Chemistry, 2017, 34(3): 316-323.

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Synthesis and Biological Activity of Novel 1,4-Pentadien-3-one Oxime Esters Bearing Heterocycle Moiety

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