Preparation ofN-chloroacetyl-N′-arylsulfonylureas and the crystal structure ofN-chloroacetyl-N′-(4-methylphenylsulfonyl)urea
Novel arylsulfonylureas were prepared by the reaction of chloroacetyl isocyanate with arylsulfamides. The structures of the compounds synthesized were determined by IR and1H NMR spectra. An X-ray structural analysis ofN-chloroacetyl-N′-(4-methylphenylsulfonyl)urea was carried out. It was found that the molecule has theanti-syn conformation stabilized by an intramolecular H-bond. In the crystal, the molecules are combined into centrosymmetrical dimers by intermolecular hydrogen bonds. The compounds considered exhibit moderate fungicide activity.
Key wordsN-chloroacetyl-N′-arylsulfonylureas X-ray diffraction analysis hydrogen bonds chloroacetyl isocyanate arylsulfamides biological activity
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- 1.V. K. Promonenkov, V. I. Sorokin, L. M. Nesterova, O. N. Fedorova, and T. E. Granina,Sul'fonilgeterilmocheviny [Sulfonylheterylureas], NIITEKhIM, Moscow, 1985 (in Russian).Google Scholar
- 2.V. I. Sorokin, S. N. Golosov, A. N. Kornilov, D. S. Yufit, Yu. T. Struchkov, and V. N. Drozd,Khim. Geterotsikl. Soedin., 1993, 960 [Chem. Heterocycl. Compd., 1993 (Engl. Transl.)].Google Scholar
- 3.USSR patent 1559660,Byul. izobret., 1990, 56.Google Scholar
- 4.T. Sotomatsu, Y. Nakagawa, and T. Fujita,Pestic. Biochem. and Physiol., 1987,27, 156.Google Scholar
- 5.W. A. Brett, P. Rademacher, and R. Boese,Acta Crystallogr., 1990,46, 880.Google Scholar
- 6.G. Husroon and G. W. M. Tiemessen,Acta Crystallogr., B, 1976,32, 1604.Google Scholar
- 7.S. Kashino and M. Haisa,Acta Crystallogr. B, 197733 855.Google Scholar
- 8.A. S. Vyazgin, D. S. Yufit, Yu. T. Struchkov, A. N. Kornilov, E. N. Vetrova, V. I. Sorokin, and V. N. Drozd,Izv. TSKhA [Bull. Timiryazev Agricult. Acad.], 1988, 180 (in Russian).Google Scholar
- 9.D. S. Yufit, Yu. T. Struchkov, A. N. Kornilov, M. A. Amanova, V. I. Sorokin, V. N. Knyazev, and V. N. Drozd,Izv. TSKhA [Bull. Timiryazev Agricult. Acad.], 1990, 185 (in Russian).Google Scholar