Issue 9, 2008
From the journal:

Green Chemistry

Potential green fungicide: 16-oxo-1-oxa-4-azoniacyclohexadecan-4-ium tetrafluoroborate

Yanhong Dong,a   Xiaomei Liang,a   Huizhu Yuan,b   Shuhua Qi,b   Fuheng Chena  and  Daoquan Wang*a  

* Corresponding authors

a Key Laboratory of Pesticide Chemistry and Application Technology, Department of Applied Chemistry, China Agricultural University, Beijing, People's Republic of China
E-mail: wangdq@cau.edu.cn
Fax: 86-10-62732219
Tel: 86-10-62732219

b Institute of Plant Protection, Chinese Academy of Agriculture Science, Beijing, People's Republic of China

Abstract

16-Oxo-1-oxa-4-azoniacyclohexadecan-4-ium tetrafluoroborate (2a) and its sulfonyl derivatives (2b–2i) were synthesized, their structures were confirmed by 1H NMR and elemental analysis and their fungicidal activities were investigated. Among them, compound 2a was not only more effective than compounds 2b–2i against the Rhizoctonia solani Kühn in vitro bioassay, but also better than the commercial fungicide Carbendazim both in pot culture experiments and field efficacy trial. These results once again proved the correctness of our original proposal that macrocyclic compounds with two polarizable groups (one hydrogen-bonding donor and one hydrogen-bonding acceptor) on the ring may have certain good bioactivity. Furthermore, 2a has low toxicity, is safe for human beings, and its synthesis is a green and most economical process, because the atoms of the starting materials are almost fully utilized.

Graphical abstract: Potential green fungicide: 16-oxo-1-oxa-4-azoniacyclohexadecan-4-ium tetrafluoroborate

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Article information

DOI
https://doi.org/10.1039/B805797D
Article type
Paper
Submitted
07 Apr 2008
Accepted
17 Jun 2008
First published
11 Aug 2008

Green Chem., 2008,10, 990-994

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Potential green fungicide: 16-oxo-1-oxa-4-azoniacyclohexadecan-4-ium tetrafluoroborate

Y. Dong, X. Liang, H. Yuan, S. Qi, F. Chen and D. Wang, Green Chem., 2008, 10, 990 DOI: 10.1039/B805797D

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