Synthesis and antifungal activity of
D
-glucopyranosyl
ureas and
D
-glucofurano-imidazolidine-2-ones
Xuan Tang
•
Feng Xue
•
Hongju Ma
•
Xiufang Cao
•
Changshui Chen
•
Xuegang Li
Received: 26 March 2012 / Accepted: 6 May 2012 / Published online: 30 June 2012
Ó Springer Science+Business Media B.V. 2012
Abstract A series of N-b-
D
-glucopyranosyl-N’-substituted phenyl ureas were
synthesized by reaction of glucosyl isocyanate with arylamines and glycosamine
with aryl isocyanates, and a series of
D
-glucofurano-imidazolidine-2-ones were
obtained via deacetylation of glycosylureas. Although some of the compounds have
already been described, most were prepared for the first time in this work. The
structures of all the compounds synthesized were confirmed by IR,
1
H NMR, and, in
part, by
13
C NMR. Antifungal activity of the title compounds was determined
against four kinds of plant pathogenic fungi, Sclerotinia sclerotiorum, Fusarium
graminearum, Fusarium oxysporum, and Bipolaris maydis. Preliminary bioassay
indicates that most of glycosylureas had some activity against S. sclerotiorum; for
some, the antifungal activity was strong. However, most of the imidazolidine-2-ones
had weak antifungal activity.
Keywords Glycosylureas Á Imidazolinone Á Synthesis Á Antifungal activity
Introduction
Glucose, an energy source of living cells and an intermediate of metabolism, exists
widely in nature and is important in biology. Because modification of medicines by
glycosyl can not only prolong and enhance their effect but also efficiently reduce
X. Tang Á F. Xue Á X. Cao Á C. Chen (&) Á X. Li (&)
College of Science, Huazhong Agricultural University, Wuhan 430070,
People’s Republic of China
e-mail: chenchang@mail.hzau.edu.cn
X. Li
e-mail: lixuegang@mail.hzau.edu.cn
H. Ma
Department of Plant Protection, Huazhong Agricultural University, Wuhan, China
123
Res Chem Intermed (2013) 39:805–820
DOI 10.1007/s11164-012-0596-8
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