Abstract
In this study, a series of p-aromatic isothiocyanates are prepared by reacting p-aromatic amines with carbon disulphide and further treating with molecular iodine to yield corresponding isothiocyanate derivatives. The structures of newly synthesized compounds are confirmed by IR, NMR, and MS data. Activity of the products against plant pathogenic fungi and bacteria is tested and the structure-activity relationship is approached. p-Nitrophenyl isothiocyanate most efficiently inhibits Rhizoctonia solani and Erwinia carotovora. The order of seven aromatic isothiocyanates antifungicidal activity is following: p-nitrophenyl > p-methoxyphenyl > p-chlorophenyl > p-methylphenyl > p-ethylphenyl > phenyl > p-fluorophenyl. For antibacterial activity, the order was p-nitrophenyl > p-chlorophenyl > p-methylphenyl > p-ethylphenyl > p-fluorophenyl > phenyl > p-methoxyphenyl. The present study indicates that some of the compounds exhibit promising antimicrobial activity and can be used as an alternative to the traditional synthetic fungicides for controlling R. solani and E. carotovora.
Similar content being viewed by others
References
Lalancette, N., Furman, L.A., and White, J.F., Crop Prot., 2013, vol. 43, p. 7. doi 10.1016/j.cropro.2012.08.006
Belakhov, V.V. and Garabadzhiu, A.V., Russ. J. Gen. Chem., 2014, vol. 84, no. 13, p. 2664. doi 10.1134/S1070363214130271
Belakhov, V.V. and Garabadzhiu, A.V., Russ. J. Gen. Chem., 2016, vol. 86, no. 13, p. 3002. doi 10.1134/S1070363216130120
Perelló, A., Lampugnani, G., Abramoff, C., Slusarenko, A., and Bello, G.D., Int. J. Pest Manage., 2016, vol. 63, no. 2, p. 157. doi 10.1080/09670874.2016.1252478
Smolinska, U., Morra, M.J., Knudsen G.R., and James, R.L., Plant Dis., 2007, vol. 87, no. 4, p. 407. doi 10.1094/pdis.2003.87.4.407
Deng, Q., Zinoviadou, K.G., Galanakis, C.M., Orlien, V., Grimi, N., Vorobiev, E., Lebovka N., and Barba, F.J., Food Eng. Rev., 2015, vol. 7, no. 3, p. 357. doi 10.1007/s12393-015-9122-2
Dufour, V., Stahl M., and Baysse, C., Microbiology, 2015, vol. 161, no. Pt 2, p. 229. doi 10.1099/mic.0.082362-0
Ugolini, L., Martini, C., Lazzeri, L., D’Avino, L., and Mari, M., Postharvest Biol. Tec., 2014, vol. 90, p. 34. doi 10.1016/j.postharvbio.2013.12.002
Ntalli, N. and Caboni, P., Phytochem. Rev., 2017, vol. 16, no. 5, p. 827. doi 10.1007/s11101-017-9491-7
Mochida, K. and Ogawa, T., J. Sci. Food Agr., 2010, vol. 88, no. 10, p. 1704. doi 10.1002/jsfa.3268
Main, M., Mccaffrey J.P., and Morra, M.J., J. Appl. Entomol., 2015, vol. 138, no. 9, p. 701. doi 10.1111/jen.12128
Bangarwa, S.K. and Norsworthy, J.K., Crop Prot., 2015, vol. 74, p. 145. doi 10.1016/j.cropro.2015.04.012
Pilyugin, V.S., Sapozhnikov, Y.E., and Sapozhnikova, N.A., Russ. J. Gen. Chem., 2004, vol. 74, no. 5, p.738.
Ko, M.O., Kim, M.B., and Lim, S.B., J. Microbiol. Biotechnol., 2016, vol. 26, no. 12, p. 2036. doi 10.4014/jmb.1606.06008
Milelli, A., Fimognari, C., Ticchi, N., Neviani, P., Minarini A., and Tumiatti, V., Mini Rev. Med. Chem., 2014, vol. 14, no. 12, p. 963. doi 10.2174/1389557514666141106131909
Li, D., Shu, Y., Li, P., Zhang, W., Ni H., and Cao, Y., Med. Chem. Res., 2012, vol. 22, no. 7, p. 3119. doi 10.1007/s00044-012-0323-4
Hansch, C., Gao, H., and Hoekman, D., A Generalized Approach to Comparative QSAR, Devillers. J., Ed., Washington, DC: Taylor and Francis, 1998, p.285.
Schultz, T.W. and Comeaux, J.L., B. Environ. Contam. Tox., 1996, vol. 56, no. 4, p. 638. doi 10.1007/s001289900093
Mays, J.R., Weller Roska, R.L., Sarfaraz, S., Mukhtar, H., and Rajski, S.R., Chembiochem., 2008, vol. 9, no. 5, p. 729. doi 10.1002/cbic.200700586
Tajima, H., Nakamoto, Y., and Taketo, A., Biosci. Biotech. Bioch., 2007, vol. 71, no. 4, p. 1094. doi 10.1271/bbb.70001
Parmeter, J., Rhizoctonia Solani, Biology and Pathology, Univ. of California Press, 1970.
Ogoshi, A., Annual Rev. phytopathol., 1987, vol. 25, no. 1, p. 125. doi 10.1146/annurev.py.25.090187.001013
Dong, Y.-H., Xu, J.-L., Li, X.-Z, and Zhang, L.-H., P. Natl. Acad. Sci. USA., 2000, vol. 97, no. 7, p. 3526. doi 10.1073/pnas.060023897
Etzenhouser, B., Hansch, C., Kapur, S., and Selassie, C.D., Bioorg. Med. Chem., 2001, vol. 9, no. 1, p. 199. doi 10.1016/S0968-0896(00)00238-8
Kuroda, K., Caputo, G.A., and DeGrado, W.F., Chem. Eur. J., 2009, vol. 15, no. 5, p. 1123. doi 10.1002/chem.200801523
Screnci, D., Mckeage, M.J., Galettis, P., Hambley, T.W., Palmer, B.D., and Baguley, B.C., Brit. J. Cancer, 2000, vol. 82, no. 4, p. 996. doi 10.1054/bjoc.1999.1026
Saksena, N.K., Folia Microbiol., 1985, vol. 30, no. 4, p. 359. doi 10.1007/BF02927591
Nath, J., Ghosh, H., Yella, R., and Patel, B.K., Eur. J. Org. Chem., 2009, vol. 2009, no. 12, p. 1849. doi 10.1002/ejoc.200801270
Author information
Authors and Affiliations
Corresponding author
Additional information
The text was submitted by the authors in English.
Rights and permissions
About this article
Cite this article
Tang, J., Niu, J., Wang, W. et al. p-Aromatic Isothiocyanates: Synthesis and Anti Plant Pathogen Activity. Russ J Gen Chem 88, 1252–1257 (2018). https://doi.org/10.1134/S1070363218060348
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363218060348