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Effects of Elemental Sulfur, Dithiocarbamates, and Related Fungicides on Organic Acid Metabolism of Fungus Spores

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Abstract

Various aspects of the mechanisms of action, insofar as they are known, of sulfur, dithiocarbamates, and related fungicides have been reviewed by McCallan (1957), Horsfall (1945), and Martin (1959). The present paper reports some comparative biochemical effects of these materials on metabolism of organic acids by way of the citric acid cycle. The purpose of the study was to determine whether all of these fungicides affect the same or different biochemical processes and to relate the observed effects to the structure and chemical properties of the compounds and the enzymes.

This work was supported in part by a grant from the Rockefeller Foundation.

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References

  • American Phytopathological Society. 1943 Committee on Standardization of Fungicidal Tests. The slide-germination method of evaluating protectant fungicides. Phytopathology, 33, 627–632.

    Google Scholar 

  • Bartlett, D., and Kwart, H. 1950 Dilatometric studies of the behavior of some inhibitors and retarders in the polymerization of liquid vinyl acetate. I. J. Am. Chem. Soc., 72, 1051–1059.

    Article  CAS  Google Scholar 

  • Calvin, M., and Sogo, P. B. 1957 Primary quantum conversion process in photosynthesis: electron spin resonance. Science, 125, 499–500.

    Article  PubMed  CAS  Google Scholar 

  • Cavallini, D., and Frontali, N. 1954 Quantitative determination of keto acids by paper partition chromatography. Biochem. et Biophys. Acta, 13, 439–445.

    Article  CAS  Google Scholar 

  • Commoner, B., Townsend, J., and Pake, G. E. 1954 Free radicals in biological materials. Nature, 174, 689–691.

    Article  PubMed  CAS  Google Scholar 

  • Commoner, B., Heise, J. J., Lippincott, B. B., Norberg, R. E., Passonneau, J.V., and Townsend, J. 1957 Biological activity of free radicals. Science, 126, 57–63.

    Article  PubMed  CAS  Google Scholar 

  • Dickman, R., and Cloutier, A. A. 1950 Activation and stabilization of aconitase by ferrous ions. Arch. Biochem., 25, 229–231.

    PubMed  CAS  Google Scholar 

  • Ehrenberg, A., and Ludwig, G.D. 1958 Free radical formation in reaction between old yellow enzyme and reduced triphosphopyridine nucleotide. Science, 127, 1177–1178.

    Article  PubMed  CAS  Google Scholar 

  • Farmer, E. H., and Shipley, F.W. 1947 The reaction of sulphur and sulphur compounds with olefinic substances. Part I. The reaction of sulphur with mono-olefins and with A 1:5-diolefins. J. Chem. Soc., 1947, 1519–1532.

    Google Scholar 

  • Farmer, E.H., Ford, J.F., and Lyons, J. A. 1954 The interaction of sulphur and sulphur compounds with olefinic substances. VII. Low-temperature sulphuration of trialkylethy-lenes with hydrogen sulphide-sulphur dioxide, and with a sulphur-zinc dithiocarbamate system. J. Appl. Chem. ( London ) 4, 554–561.

    Google Scholar 

  • Gardner, D. M., and Fraenkel, G. K. 1954 Paramagnetic resonance in liquid sulfur. J. Am. Chem. Soc., 76, 5891–5892.

    Article  CAS  Google Scholar 

  • Gardner, D. M., and Fraenkel, G. K. 1956 Paramagnetic resonance of liquid sulfur: determination of molecular properties. J. Am. Chem. Soc., 78, 3279–3288.

    Article  CAS  Google Scholar 

  • Gee, G. 1952 The molecular complexity of sulphur in the liquid and vapour. Trans. Faraday Soc., 48, 515–526.

    Article  CAS  Google Scholar 

  • Goksyr, J. 1955 The effect of some dithiocarbamyl compounds on the metabolism of fungi. Physiol. Plantarum, 8, 719–835.

    Article  Google Scholar 

  • Haber, F., und Willstatter, R. 1931 Unpaarigkeit und Radikalketten im Reaktionsmechan-ismus organischer und enzymatischer Vorgange. Ber. Deut. Chem. Ges., 64B, 2844–2856.

    Article  CAS  Google Scholar 

  • Hirshon, J.M., Gardner, D. M., and Fraenkel, G. K. 1953 Evidence for the existence of radicals in the presence of Lewis acids. J. Am. Chem. Soc., 75, 4115.

    Article  CAS  Google Scholar 

  • Horsfall, J. G. 1945 Fungicides and their action. 239pp. Chronica BotanicaCo., Waltham, Mass.

    Google Scholar 

  • Hoshino, T., Yamagishi, K., and Lchikawa, Y. 1953 On the photochemical addition reaction of methylmercaptane with vinylacetate, vinylchloride, and allylalcohol. Proc. Japan. Acad., 29, 55.

    CAS  Google Scholar 

  • Kern, R. J. 1955 Some sulfur compounds as polymerization sensitizers. J. Am. Chem. Soc., 77, 1382–1383.

    Article  CAS  Google Scholar 

  • Ludwig, R. A., Thorn, G. D., and Unwin, C. H. 1955 Studies on the mechanism of fungicidal action of metallic ethylenebisdithiocarbamates. Can. J. Botany, 33, 42–59.

    Article  CAS  Google Scholar 

  • McCallan, S. E. A. 1957 Mechanisms of toxicity with special reference to fungicides. Proc. Second Internat. Plant Prot. Conf. 1956. Fernhurst, England, pp. 77–95.

    Google Scholar 

  • McCallan, S. E. A., and Miller, L. P. 1957 Equimolar formation of carbon dioxide and hydrogen sulfide when fungus tissue reduces sulfur. Contrib. Boyce Thompson Inst., 18, 497–506.

    CAS  Google Scholar 

  • McCallan, S. E. A., Miller, L. P., and Weed, R. M. 1954 Comparative effect of fungicides on oxygen uptake and germination of spores. Contrib. Boyce Thompson Inst., 18, 39–68.

    Google Scholar 

  • McCallan, S. E. A., and Wilcoxon, F. 1931 The fungicidal action of sulphur. II. The production of hydrogen sulphide by sulphured leaves and spores and its toxicity to spores. Contrib. Boyce Thompson Inst., 3, 13–38.

    CAS  Google Scholar 

  • Manten, A., Klopping, H. L., and van der Kerk, G. J.M. 1951 Investigations on organic fungicides. III. The influence of essential trace metals upon the fungitoxicity of tetra-methylthiuram disulphide and 8-hydroxyquinoline. Antonie van Leeuwenhoek, 17, 58–68.

    Article  PubMed  CAS  Google Scholar 

  • Martin, H. 1959 The Scientific Principles of Crop Protection. 359 pp. Edward Arnold ( Publishers) Ltd., London. 4th ed.

    Google Scholar 

  • Meyerhof, O. 1951 Aldolase and isomerase.ii: Sumner, J. B., and Myrback, K., editors. The Enzymes. Vol. II, pt. 1, pp. 162–182. Academic Press, Inc., New York.

    Google Scholar 

  • Michaelis, L. 1951 Theory of oxidation-reduction. In: Sùmner, J. B., and Myrback, K., editors. The Enzymes. Vol. II, pt. 1, pp. 1–54. Academic Press, Inc., New York.

    Google Scholar 

  • Michaelis, L., and Smythe, C.V. 1938 Biological oxidations and reductions. Ann. Rev. Biochem., 7, 1–36. 1938.

    Google Scholar 

  • Miller, L. P., McCallan, S.E.A., and Weed, R. M. 1953 Quantitative studies on the role of hydrogen sulfide formation in the toxic action of sulfur to fungus spores. Contrib. Boyce Thompson Inst., 17, 151–171.

    CAS  Google Scholar 

  • Ochoa, S. 1951 Fumarase and aconitase. In’-Sumner, J. B., and Myrback, K., editors. The Enzymes. Vol. 1, pt. 2, pp. 1217–1236. Academic Press, Inc., New York.

    Google Scholar 

  • Owens, R. G. 1953 Studies on the nature of fungicidal action. I. Inhibition of sulfhydryl-, amino-, iron-, and copper-dependent enzymes in vitro by fungicides and related compounds. Contrib. Boyce Thompson Inst., 17, 221–242.

    CAS  Google Scholar 

  • Owens, R. G. 1954 Studies on the nature of fungicidal action. III. Effects of fungicides on polyphenol oxidase in vitro. Contrib. Boyce Thompson Inst., 17, 473–487.

    Google Scholar 

  • Owens, R. G., Novotny, H. M., and Michels, M. 1958 Composition of conidia of Neurospora sitophila. Contrib. Boyce Thompson Inst., 19, 355–374.

    CAS  Google Scholar 

  • Owens, R. G., and Novotny, H. M. 1958 Mechanism of action of the fungicide dichlone (2, 3-dichloro-l,4-naphthoquinone). Contrib. Boyce Thompson Inst., 19, 463–482.

    Google Scholar 

  • Owens, R. G., and Novotny, H. M. 1959 Mechanism of action of the fungicide captan [N-(trichloromethylthio)-4-cyclohexene-l,2-dicarboximide]. Contrib. Boyce Thompson Inst., 20, 171–190.

    CAS  Google Scholar 

  • Palmer, J.K. 1955 Chemical investigations of the tobacco plant. X. Determination of organic acids by ion exchange chromatography. Conn. Agr. Expt. Sta. Bull. 589. 31 pp. Powell, R. E., and Eyring, H. 1943 The properties of liquid sulfur. J. Am. Chem. Soc., 65, 648–654.

    Article  Google Scholar 

  • Ryan, F. J., Beadle, G. W., and Tatum, E. L. 1943 The tube method of measuring growth rate of Neurospora. Am. J. Botany, 30, 784–799.

    Article  Google Scholar 

  • Sijpesteyn. A. K. and van der Kerk, G. J. M. 1954a Investigations on organic fungicides. VIII. The biochemical mode of action of bisdithiocarbamates and diisothiocyanates. Biochim. et Biophys. Acta, 13, 545–552.

    Article  CAS  Google Scholar 

  • Sijpesteyn, A. K., and van der Kerk, G. J. M. 1954b Investigations on organic fungicides. IX. The antagonistic action of certain imidazole derivatives and of a-keto acids on the fungitoxicity of dimethyldithiocarbamates. Biochim. et. Biophys. Acta, 15, 69–77.

    Article  CAS  Google Scholar 

  • Sijpesteijn, A.K., and van der Kerk, G.J. M. 1956 Investigations on organic fungicides. X. Pyruvic acid accumulation and its relation to the phenomenon of inversion growth as affected by sodium dimethyldithiocarbamate. Biochim. et Biophys. Acta, 19, 280–288.

    Article  CAS  Google Scholar 

  • Sisler, H.D., and Marshall, N. L. 1957 Physiological effects of certain fungitoxic compounds on fungus cells. J. Wash. Acad. Sci., 47, 321–329.

    CAS  Google Scholar 

  • Sogo, P. B., Pon, N.G., and Calvin, M. 1957 Photo spin resonance in chlorophyll-containing plant material. Proc. Nat. Acad. Sci. U.S., 43, 387–393.

    Article  CAS  Google Scholar 

  • Tollin, G., and Calvin, M. 1957 The luminescence of chlorophyll-containing plant material. Proc. Nat. Acad. Sci. U.S., 43, 895–908.

    Article  CAS  Google Scholar 

  • Walling, C. 1957 Free Radicals in Solution. 631 pp. John Wiley and Sons, Inc., New York.

    Google Scholar 

  • Weed, R.M., McCallan, S.E.A., and Miller, L. P. 1953 Factors associated with the fungitoxicity Qf ferbam and nabam. Contrib. Boyce Thompson Inst., 17, 299–315.

    CAS  Google Scholar 

  • Zentmyer, G. A. 1944 Inhibition of metal catalysis as a fungistatic mechanism. Science, 100, 294–95.

    Article  PubMed  CAS  Google Scholar 

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Owens, R.G. (1960). Effects of Elemental Sulfur, Dithiocarbamates, and Related Fungicides on Organic Acid Metabolism of Fungus Spores. In: Developments in Industrial Microbiology. Springer, Boston, MA. https://doi.org/10.1007/978-1-4899-5073-4_25

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  • DOI: https://doi.org/10.1007/978-1-4899-5073-4_25

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4899-5075-8

  • Online ISBN: 978-1-4899-5073-4

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