Abstract
A series of 12 pyrimidine derivatives were prepared and tested in vitro against growth, sporulation and nucleic acids ofFusarium oxysporum f. sp.lycopersici andHelminthosporium oryzae. Introduction of thiazole ring together with two aryl groups to 2-aminopyrimidine induced drastic toxicity for both fungi. Pyrimidine derivatives with aryl groups were less toxic. Nitro groups were found to enhance the toxicity of the pyrimidine derivatives especially when substituted in ortho-position of the aryl groups. Inhibition of nucleic acids synthesis of both fungi was attributed mainly to the presence of thiazole ring.
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Literature Cited
Ashwell, G.,Methods in Enzymology. III. Interscience Publishers, Inc. New York, 1957, p.81.
Awad, I. M. A., Abdel-Rahman, A. I. and Bakhite, E. A., Synthesis and application of some new S-(substituted) thio-and thienoquinoline derivative and antimicrobial agents.Collect. Czech. Chem. Commun., 56, 1749–60 (1991).
Burton, K.,Methods in Enzymology. Vol. 12 part B. Interscience Publishers, Inc. New York, 1968, p.163.
Cerkauskas, R. F., Verma, P. R. and McKenzie, D. L., Effects of herbicides on in vitro growth and carpogenic germination of Sclerotinia sclerotiorum.Canadian Journal of Plant Pathology, 8, 161–166 (1986).
Cole, A. M., Turner, J. A. W. and Snell, B. K., Fungicidal 2-amino-4-(sulfamoyloxy)-6-methylpyrimidines.Ger. Offen., 2,246–645 (1973).
Cremyln, R. J.,Pesticides Preparation and Mode of Action, Wiley, Chickester, 1978, p.54.
Ebert, E. and Dumford, S. W., In Gunther, F. A. (Eds.),Residue Reviews, Vol. 65, Springer-Verlag, New York, 1976.
Elbe, H., Dutzmann, S. and Reinecke, P., Pr$$ and testing of (aryloxy)-, (arylsufinyl)-, and (arylsulfonyl) oxoalkylpyrimidines as agrochemical fungicides.Ger. Offen. DE 3,702,962 (1988).
Esser, H. O., Depuis, G., Ebert, E., Marco, G. and Vogel, C., In Kearney, P. C. and Kaufman, D. D. (Eds.)Herbicides-Chemistry, Degradation and Mode of Action. Vol. 1, Dekker, New York, 1976, p.129.
Hammad, A., El-Sayed, A. S., Islam, I. E., Shafik, N., Synthesis of 3-(2-benzimidazolyl) coumarins of anticipated biological activity.J. Chem. Soc. Pak., 12, 292–6 (1990).
Huxley, A., Kunz, W., Ackermann, P. and Sutter, M., Benzothienyl- and benzofuryl pyrrolecarbonitrile fungicides.Eur. Pat. Appl., EP. 404,721 (1990).
Igwegbe, E. C. K. and Salary, J. 6-Methyl purine induced inhibition of selerotia morphogensis in Sclerotium rolfsii and its reversal by adenosine.Mycopathologia, 62, 153–159 (1977).
Ismail, I. M. K., Salama, A. M., Ali, M. I. A. and Ouf, S. A., Effect of some phenolic compounds on spore germination and germ-tube length of Aspergillus fumigatus and Fusarium oxysporum f. sp.Lycopersici.Cryptogamie Mycol., 8, 51–60 (1987).
Kharchuk, A. N., Protopopova, G. V., Telyuk, V. G., Fedotov, K. V. and Mikitenko, E. K., Biological activity of thiazole and pyrimidine derivatives.Fiziol. Akt. Veshchestva, 20, 21–6 (1988).
Kuhr, R. J. and Dorough, H. W.,Carbamate Insecticides: Chemistry, Biochemistry and Toxicology. CRC Press, Cleveland, 1976.
Kunz, W., and Schurter, R., Preparation of 1,2,3-benzo-thiadiazole derivatives and their use for protecting plants against diseases.Eur. Pat. Appl., EP, 420,803 (1991).
Lowen, G. T., Process for preparation of insecticidal, acaricidal and molluscicidal 2-halopyrrole-3-carbonitrile compounds.U.S. Pat. US 5,041,556 (1991).
Mehta, R. J., Swithenbank, C. and Lidert, Z., Preparation of quinone derivatives as microbicidal and plant growth regulating compounds.U. S. Pat., US 4,975,459 (1990).
Nezu, M., Nagata, T., Masudag, K. and Ito, S., Preparation of 2 alkylsulfonyl- or 2-benzylsulfonyl pyrimidine derivatives as agrochemical fungicides.Jpn. Koka; Tokkyo Koho JP 63 23,870 (1986).
Porter, D. M. and Rud, O. E., Suppression of Sclerotinia blight of peanuts with dinitrophenol herbicides.Phytopathol., 70, 720–722 (1980).
Shortle, W. C., Tattar, T. A. and Rich, A. E., Effect of some phenolic compounds on growth of phialophoramelinii and Fomes connatus.Phytopathology, 61, 552–555 (1971).
Singh, H., Yadav, L. D. S., Shukla, K. N. and Dwivedi, R., Synthesis and fungitoxicity of some new thiazolo [2,3-c]-1,2,4-triazole derivatives.Indian J. Pharm. Sci., 53, 1–5 (1991).
Skipp, R. A. and Bailey, J. A., The effect of phaseollin on the growth of Colletotrichum lindemuthianum in bioassays designed to measure fungitoxicity.Physiological Plant Pathology, 9, 253–263 (1976).
Spendley, P. J. and Ride, J. P., Fungitoxic effects of two alka-2,4-dienals, α-and B-triticene, isolated from wheat.Trans. Br. Mycol. Soc., 82, 283–288 (1984).
Tsuboi, S. and Honda, I., Synergistic insecticides containing nitro compounds and acephate.Faming Zhuanli Shenping Gongkai Schuomingshu, CN 1,045,333 (1990).
West, T. P., Metabolism of pyrimidine bases and nucleosides by Pseudomonas fluorescens biotype F.Microbios, 56, 27–36 (1988).
Woodcock, D., In March, R. W. (Eds.),Systemic Fungicides, Longman, London, 1977, p.63.
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Ouf, S.A., Sherif, S.M. Synthesis and fungitoxicity of some pyrimidine derivatives. Arch. Pharm. Res. 16, 62–67 (1993). https://doi.org/10.1007/BF02974130
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DOI: https://doi.org/10.1007/BF02974130