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Herbicidal Metabolites from a Soil-Dwelling Fungus (Scopulariopis brumptii)

  • Jamin Huang (a1), Alan R. Putnam (a2), Georgina M. Werner (a1), Saroj K. Mishra (a2) and Curt Whitenack (a2)...


The fungus Scopulariopis brumptii Salvanet-Duval (MSU 42018) was isolated from a soil sample collected from the rhizosphere of a potted asparagus plant. When cultured 7 days in A-9 broth medium, the organism produced compounds phytotoxic to seeding dicotyledonous weeds (via foliar application) and to Chlamydomonas reinhardtii Dangeard. Three herbicidal metabolites, 3-hydroxybenzyl alcohol, 2-methylhydroquinone, and (+)-epiepoformin, were isolated by column and thin-layer chromatography (TLC) and structures confirmed by Fourier transform infrared spectroscopy (FT-IR), nuclear magnetic reasonance spectroscopy (NMR), and mass spectrometry (MS). Of the three compounds, (+)-epiepoformin was the most active, providing complete control of redroot pigweed and 88% control of white mustard when applied at 4.4 kg/ha.



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1. Barron, G. L. 1968. The genera of hyphomycetes from soil. Pages 275279. Williams and Wilkins, Baltimore.
2. Basalkevich, E. D., Cherepenko, T. I., Vysotskii, N. N., Shapovalenko, V. F., and Svishchuk, A. A. 1971. Synthesis and fungicidal activity of methylated hydroquinones. Fiziol. Aktiv. Veshchestva Respub. Mezhvedom. Sb. 3, 174180.
3. Bottger, G. T., Yerington, A. P., and Gertler, S. I. 1951. Synthetic organic compounds as insecticides, U.S. Dep. Agric. Bur. Entomol. and Plant Quarantine E-826. 23 pp.
4. Carey, S. T. and Nair, M.S.R. 1979. Metabolites of pyrenomycetes. X. Isolation of P-toluquinone and toluquinol from Nectria erubescens . J. Nat. Prod. 42:231.
5. Carlson, S. D. 1967. Paraquinone secretion by confused flour beetles after carbon dioxide or nitrogen anesthesia. J. Econ. Entomol. 60:878879.
6. Cutler, H. G. 1986. Isolating, characterizing, and screening mycotoxins for herbicidal activity. Pages 147170 in Putnam, A. R. and Tang, C. S., eds. The Science of Allelopathy, Wiley-Interscience, New York.
7. DeFrank, J. and Putnam, A. R. 1985. Screening procedures to identify soil-borne actinomycetes that can produce herbicidal compounds. Weed Sci. 33:271274.
8. Dettner, K. and Schwinger, G. 1982. Defensive secretions of three oxytelinge rove beetles (Coleoptera: Straphylinidae). J. Chem. Ecol. 8:14111412.
9. Duke, S. O. 1986. Microbially produced phytotoxins as herbicides – a perspective. Pages 287394 in Putnam, A. R. and Tang, C. S., eds. The Science of Allelopathy. Wiley-Interscience, New York.
10. Emmons, C. W., Chapman, H. B., Utz, J. P., and Kwon-Chung, K. J. 1977. Medical Mycology. Lea and Febiger, Philadelphia. Page 540.
11. Englehardt, M., Rapaport, H., and Sokoloff, A. 1965. Odorous secretion of normal and mutant Tribolium confusum . Science 150:632633.
12. Fischer, H. P. and Bellus, D. 1983. Phytotoxicants from microorganisms and related compounds. Pestic. Sci. 14:334346.
13. Heisey, R. M., DeFrank, J., and Putnam, A. R. 1985. A survey of soil microorganisms for herbicidal activity. Pages 337349 in Thompson, A. C., ed. The Chemistry of Allelopathy. ACS Symp. Ser. No. 268.
14. Hess, F. D. 1980. A Chlamydomonas algal bioassay for detecting growth inhibitor herbicides. Weed Sci. 28:515520.
15. Ichihara, A., Kimura, R., Oda, K., Moriyasu, K., and Sakamura, S. 1982. Synthesis of (±)-epoxydon and related natural compounds. Agric. Biol. Chem. 46:18791883.
16. Ichihara, A., Moriyasu, K., and Sakamura, S. 1978. Synthesis of (±)-epoformin (desoxyepoxydon) and (±)-epiepoformin (desoxyepiepoxydon). Agric. Biol. Chem. 42:24212422.
17. Ichikawa, Y. and Tsuruta, H. 1975. Methylhydroquinone insecticides. Japan 75, 107, 126 (8-23-1975).
18. Jarvis, B. B., Pavanasasivam, G., and Bean, G. A. 1985. Mycotoxin production from myrothecium species. Page 227 in Lacey, J., ed. Trichothecenes and Other Mycotoxins. Academic Press, London.
19. Jarvis, B. B. and Yatawara, C. S. 1986. Roritoxins, new macrocyclic trichothecenes from Myrothecium roridum . J. Org. Chem. 61:29062910.
20. Krepinsky, J. 1961. Chemistry of defensive substances of the bombardier beetle, Brachynus selopeta, B. explodens, B. crepitans. Chem. Listy. 55:719721.
21. Misato, T. 1982. Recent status and future aspects of agricultural antibiotics. Pages 241246 in Takahashi, et al., eds. Pesticide Chemistry: Human Welfare and the Environment. Vol. 2. Natural Products, Pergamon Press, Oxford–New York.
22. Mishra, S. K., Taft, W. H., Putnam, A. R., and Ries, S. K. 1987. Plant growth regulatory metabolites from novel actinomycetes. J. Plant Growth Regul. 6:7584.
23. Nagasawa, H. 1979. Analogues of epoxydon. Bokin Bobai. 7:T221T225.
24. Nagasawa, H., Suzuki, A., and Tamura, S. 1978. Isolation and structure of (+)-desoxyepiepoxydon and (+)-epiepoxydon, phytotoxic fungal metabolites. Agric. Biol. Chem. 42:13031304.
25. Owens, R. G. 1953. Studies on the nature of fungicidal action. II. Chemical constitution of benzenoid and quinonoid compounds in relation to fungi toxicity and inhibition of amino and sulfhydryl-dependent enzymes. Contrib. Boyce Thompson Inst. 17:273282.
26. Questel, D. D. and Gertler, S. I. 1952. Laboratory tests of toxicity of some organic compounds to the European corn borer. Bur. Entomol., Plant Quarantine E-840. 12 pp.
27. Rebstock, M. C. 1964. New metabolite of patulin-producing penicillia. Arch. Biochem. Biophys. 104:156159 (1964).
28. Sager, R. and Granick, S. 1953. Nutritional studies with Chlamydomonas reinhardtii . Ann. N.Y. Acad. Sci. 56:831838.
29. Scheffer, R. P. 1983. Toxins as chemical determinants of plant disease. Pages 140 in Doly, J. M. and Deverall, B. J., eds. Toxins and Plant Pathogenesis, Academic Press, New York.
30. Scott, A. I. and Yalpani, M. 1967. A mass-spectrometric study of biosynthesis: conversion of deutero-m-cresol in patulin. Chem. Commun. 945.
31. Sequin-Frey, M. and Tamm, C. 1971. Gentisinacetal and chlor-gentisin-alkohol, zwei neve metabolite einer Phoma species. Helv. Chim. Acta 54:851861.
32. Sekizawa, Y. and Takematau, T. 1983. How to discover new antibiotics for herbicidal use. Pages 261268 in Takahashi, N., Yoshioka, H., Misato, T., and Matsunaka, S., eds. Pesticide Chemistry, Human Welfare and the Environment. Vol. 2. Natural Products, Pergamon Press, Oxford.
33. Sun, H., Chen, Z., Xu, G., and Xu, L. 1982. Quantitative structure-activity relationship of the antibiotic properties of a series of hydroquinones. Xaoxue Xuebao 17:107111.
34. Takeda Chem. Ind. Ltd. 1983. Catechols and hydroquinones as termite-controlling agents. Jap. Patent No. 58, 157, 703.
35. Yamamoto, I., Mizuta, E., Henmi, T., Yamano, T., and Yamatodani, S. 1973. Penicillium claviforme bainier epoformin. J. Takeda Res. Lab. 32:532538.
36. Yoshino, Y., Sato, C., and Maeda, S. 1974. Plant growth regulator. Jap. Patent No. 73, 041, 992.


Herbicidal Metabolites from a Soil-Dwelling Fungus (Scopulariopis brumptii)

  • Jamin Huang (a1), Alan R. Putnam (a2), Georgina M. Werner (a1), Saroj K. Mishra (a2) and Curt Whitenack (a2)...


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