Potential green fungicide: 16-oxo-1-oxa-4-azoniacyclohexadecan-4-ium tetrafluoroborate
Potential green fungicide: 16-oxo-1-oxa-4-azoniacyclohexadecan-4-ium tetrafluoroborate
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DOI：
10.1039/b805797d
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发表时间：
2008-01-01
期刊：
影响因子：
9.8
通讯作者：
Wang, Daoquan
中科院分区：
文献类型：
--
作者：
Dong, Yanhong;Liang, Xiaomei;Wang, Daoquan
合成了16-氧代-1-氧杂-4-氮鎓环十六烷-4-鎓四氟硼酸盐（2a）及其磺酰基衍生物（2b-2 i），其结构经1HNMR和元素分析确证，并研究了它们的杀菌活性。其中，化合物2a对水稻立枯病的抑制效果优于化合物2b-2 i，盆栽试验和田间药效试验均优于市售杀菌剂多菌灵。这些结果再次证明了我们原先提出的环上有两个可极化基团（一个氢键供体和一个氢键受体）的大环化合物可能具有一定的生物活性的正确性。此外，2a具有低毒性，对人类是安全的，并且其合成是绿色和最经济的方法，因为起始材料的原子几乎被完全利用。
16-Oxo-1-oxa-4-azoniacyclohexadecan-4-ium tetrafluoroborate (2a) and its sulfonyl derivatives (2b-2i) were synthesized, their structures were confirmed by (1)H 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 Kuhn 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.