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Synthesis, Crystal Structure and Bioactivities of N-(2,6-Difluorobenzoyl)-N′-[5-(Pyrid-4-yl)-1,3,4-Thiadiazol-2-yl]Urea

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Abstract

N-(2,6-difluorobenzoyl)-N′-[5-(pyrid-4-yl)-1,3,4-thiadiazol-2-yl]urea, 3, has been synthesized by reaction of 2-amino-5-(pyrid-4-yl)-1,3,4-thiadiazole with 2,6-difluorobenzoyl isocyanate, and its structure was characterized with X-ray crystallographic, NMR, MS and IR techniques. It crystallizes in the triclinic space group P − 1, with a = 7.0821(9) Å, b = 9.4896(13) Å, c = 11.6594(15) Å, α = 82.311(2)°, β = 82.328(2)°, and γ = 87.641(2)°. In the title compound, the urea scaffold in each molecule is essentially planar due to the presence of intramolecular N–H···O hydrogen bond. The molecules are linked by intermolecular complementary N–H···O hydrogen bonds into centrosymmetric R 22 (8) dimers. Intermolecular π–π stacking interactions are also present. The preliminary bioassay shows that the title compound exhibits excellent fungicidal activities against Rhizoctonia solani, Botrytis cinerea and Dothiorella gregaria.

Index Abstract

N-(2,6-difluorobenzoyl)-N′-[5-(pyrid-4-yl)-1,3,4-thiadiazol-2-yl]urea has been synthesized and characterized with X-ray crystallographic, NMR, MS and IR techniques. The preliminary bioassay shows that the title compound exhibits excellent fungicidal activities.

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Acknowledgments

Financial support of this work by the National Natural Science Foundation of China (grant No. 20072009), Natural Science Foundation of Hubei Province (grant No. 2007ABA001) and the Scientific Research Fund for Distinguished Young Scholar of Hubei Provincial Department of Education (grant No. Q200729001) are acknowledged.

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Authors and Affiliations

  1. Key Laboratory of Biologic Resources Protection and Utilization of Hubei Province, Hubei Institute for Nationalities, Enshi, Hubei, 445000, P.R. China

    Xin-Jian Song

  2. School of Chemical and Environmental Engineering, Hubei Institute for Nationalities, Enshi, Hubei, 445000, P.R. China

    Xin-Jian Song & Xiao-Hong Tan

  3. College of Chemistry, Central China Normal University, Wuhan, 430079, P.R. China

    Yan-Gang Wang

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  1. Xin-Jian Song
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  2. Xiao-Hong Tan
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  3. Yan-Gang Wang
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Correspondence to Xin-Jian Song.

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Song, XJ., Tan, XH. & Wang, YG. Synthesis, Crystal Structure and Bioactivities of N-(2,6-Difluorobenzoyl)-N′-[5-(Pyrid-4-yl)-1,3,4-Thiadiazol-2-yl]Urea. J Chem Crystallogr 38, 479–482 (2008). https://doi.org/10.1007/s10870-008-9357-3

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