Synthesis, antiviral and antifungal bioactivity of 2-cyano-acrylate derivatives containing phosphonyl moieties

Alkyl 2-cyano-3-methylthio-3-phosphonylacrylates were synthesized by the reaction of alkyl 2-cyano-3,3-dimethylthioacrylates with dialkyl phosphites. The structures of the new compounds were characterized by elemental analyses, IR, 1H-, 13C- and 31P-NMR spectral data. These compounds were tested in...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2007-05, Vol.12 (5), p.965-978
Main Authors: Lv, Yin-Pu, Wang, Xian-You, Song, Bao-An, Yang, Song, Yan, Kai, Xu, Guang-Fang, Bhadury, Pinaki S, Liu, Fang, Jin, Lin-Hong, Hu, De-Yu
Format: Article
Language:English
Subjects:
2-Cyanoacrylate
Agricultural production
antifungal activity
Antifungal Agents - chemical synthesis
Antifungal Agents - pharmacology
antiviral activity
Antiviral Agents - chemical synthesis
Antiviral Agents - pharmacology
Bioassays
Biological activity
Enbucrilate - chemical synthesis
Enbucrilate - pharmacology
Fungi
Fungicides
Fusarium - drug effects
Magnetic Resonance Spectroscopy
Microbial Sensitivity Tests
Pesticides
phosphonyl moiety
R&D
Research & development
Spectrophotometry, Infrared
synthesis
Temperature
Tobacco Mosaic Virus - drug effects
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Summary:Alkyl 2-cyano-3-methylthio-3-phosphonylacrylates were synthesized by the reaction of alkyl 2-cyano-3,3-dimethylthioacrylates with dialkyl phosphites. The structures of the new compounds were characterized by elemental analyses, IR, 1H-, 13C- and 31P-NMR spectral data. These compounds were tested in vitro against pathogenic fungi, namely, Fusarium graminearum, Cytospora mandshurica and Fusarium oxysporum. Amongst all compounds, 2d and 2t were found to be effective against the tested fungi at 50 microg/mL. A half-leaf method was used to determine the in vivo protective, inactivation and curative efficacies of the title products against tobacco mosaic virus (TMV). Title compounds 2a and 2b were found to possess good in vivo curative, protection and inactivation effects against TMV with inhibitory rates at 500 mg/L of 60.0, 89.4 and 56.5 and 64.2, 84.2 and 61.2 %, respectively. To the best of our knowledge, this is the first report on the antiviral and antifungal activity of alkyl 2-cyano-3-methylthio-3-phosphonylacrylates.
ISSN:1420-3049
1420-3049
DOI:10.3390/12050965