Synthesis and Fungicidal Activity of 12-Alkoxyiminothiopentadecanlactones

A series of novel 12-alkoxyiminothiopentadecanlactones were synthesized starting from 2-nitrocyclododecanone by Michael addition to acrolein, followed by selective reduction of the aldehyde group, conversion of hydroxyl group to mercapto group, ring expansion, Nef reaction, and finally reaction with...

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Bibliographic Details
Published in:Phosphorus, sulfur, and silicon and the related elements sulfur, and silicon and the related elements, 2014-10, Vol.189 (10), p.1529-1538
Main Authors: Meng, Chen, Li, Jian-jun, Liang, Xiao-mei, Zhang, Jian-jun, Wang, Dao-quan
Format: Article
Language:English
Subjects:
12-alkoxyimino-1,15-thiopentadecanlactone
12-nitro-1,15-thiopentadecanlactone
12-oxo-1,15-thiopenta- decanlactone
fungicidal activity
NMR
Nuclear magnetic resonance
Sulfur
Synthesis
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Summary:A series of novel 12-alkoxyiminothiopentadecanlactones were synthesized starting from 2-nitrocyclododecanone by Michael addition to acrolein, followed by selective reduction of the aldehyde group, conversion of hydroxyl group to mercapto group, ring expansion, Nef reaction, and finally reaction with alkoxyamines. Their structures were confirmed by 1 H NMR, 13 C NMR spectra, and mass spectrometry. The Z and E isomers of some of the title compounds were separated by column chromatography and their configurations were determined by 1 H NMR. These compounds showed excellent fungicidal activity against P. asparagi and are better than the commercial fungicide chlorothalonil. The results indicated that replacing an oxygen atom or NH group by sulfur atom may be an effective approach to improve the fungicidal activity or change the fungicidal spectrum of macrolactones and macrolactams.
ISSN:1042-6507
1563-5325
DOI:10.1080/10426507.2014.884095