Skip to main content

Abstract

Plant pathogens are able to affect weedy plants, in part because of the phytotoxins produced by them. Phytotoxins of weedy pathogens are produced in culture media by most of the phytopathogenic fungi of weeds that we have studied. In many cases, the phytotoxins belong to a family of related compounds produced by the pathogen. These phytotoxins belong to a wide array of chemical substances including sesquiterpenoids, sesterterpenoids, diketopiperadines, peptides, spirocyclic lactams, isocoumarins and polyketides. Biological activity is usually observed in the range of 10-3 to 10-6M concentration. The concept of using these molecules and related compounds as herbicides should be explored.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 129.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 169.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 169.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Agrios, G. N. (1988). Plant Pathology. 3rd Edition. New York: Academic Press, USA.

    Google Scholar 

  2. Bunkers, G. J. and Strobel, G. (1991). Fate of petasol, a phytotoxin produced by Drechslera gigantea in plants. Plant Science 77: 155–161.

    Article  CAS  Google Scholar 

  3. Bunkers, G. J. and Strobel, G. (1991). A proposed mode of action for green island introduction by eremophilane phytotoxins produced by Drechslera gigantea. Physiological and Molecular Plant Science 38: 313–323.

    Article  CAS  Google Scholar 

  4. Canales, M. W. and Gray, G. R. (1988). 6-Epiophiobolin A and 3-anhydro- 6-epiophiobolin A- host specific phytotoxins of Drechslera maydis (race T). Phytochemistry 27: 1653–1663.

    Article  CAS  Google Scholar 

  5. Carlson, H., Nisson, P., Jansson, H.B. and Odham, G. (1991). Characterization and determination of prehelminthosporol, a toxin from the plant pathogenic fungus, Bipolaris sorokiniana using liquid chromatography/ mass spectroscopy. Journal of Microbiological Methods 13: 259–69.

    Article  CAS  Google Scholar 

  6. Canonica, L., Beretta, M. G., Colombo, L., Gennari, C., Ranzi, B. M. and Scolastico, C. (1980). Biosynthesis of cochlioquinones. Journal of Chemical Society, Perkin Transactions 1: 2686–2690.

    Article  Google Scholar 

  7. Coval, S. J., Hradil, C. M., M. Lu, H. S., Clardy, J., Satouri, S. and Strobel, G. (1990). Pyrenokine-A and -B, two new phytotoxins from Pyrenophora teres. Tetrahedron Letters 31: 2117–2120.

    Article  CAS  Google Scholar 

  8. Cuq, F., Herrmenn-Gorline, S., Klaebe, A., Rossignol, M. and Petitprez, M. (1993). Monocerin in Exserohilum turticum isolates from maize and a study of its phytotoxicity. Phytochemistry 34: 1265–1270.

    Article  Google Scholar 

  9. Friis, P., Olsen, C. E. and Moller, B. L. (1991). Toxin production in Pyrenophora teres, the Ascomycete causing the Net-Spot blotch disease of barley (Hordeum vulgare L.). Journal of Biological Chemistry 266: 1332–1335.

    Google Scholar 

  10. Hallock, Y. (1988). Isolation and Characterization of Novel Phytotoxins From Pathogenic Fungi. Ph D. thesis. Ithaca, New York: Cornell University, U. S. A.

    Google Scholar 

  11. Hallock, Y. F., Clardy, J., Kenfield, D. and Strobel, G. (1988). De-O-methyldiaporthin, a phytotoxin from Drechslera siccans. Phytochemistry 27: 3123–3125.

    Article  CAS  Google Scholar 

  12. Hallock, Y. F., Liu, H. S. M., Clardy, J., Strobel, G., Sugawara, F., Samsoedin, R. and Yoshida, S. (1993). Triticones, spirocyclic lactams from the fungal plant pathogen Drechslera tritici-repentis. Journal of Natural Products 56: 747–754.

    Article  CAS  Google Scholar 

  13. Holm, L. G., Plucknet, D. L., Pancho, J. V. and Herberger, J. P. (1977). The World Worst Weeds: Distribution and Biology. Hawaii: University press.

    Google Scholar 

  14. Kenfield, D., Bunkers, G., Strobel, G. and Sugawara, E. (1988). Potential new herbicide-phytotoxins from plant pathogens. Weed Technology 2: 519–524.

    CAS  Google Scholar 

  15. Kenfield, D., Bunkers, G., Woo, Y. H., Strobel, G., Sugawara, F., Hallock, Y. F. and Clardy, J. (1989). Gigantenone, a novel sesquiterpene phytohormone mimic. Experientia 45: 900–902.

    Article  CAS  Google Scholar 

  16. Kenfield, D. S., Hallock, Y. F., Clardy, J. and Strobel, G. A. (1988). Curvulin, and O-methylcurvulinic acid: phytotoxic metabolites of Drechslera indica which causes necrosis on purslane and spiny amaranthus. Plant Science 60: 123–127.

    Article  Google Scholar 

  17. Kim, J. M., Hyeon, S. B., Isogai, A. and Suzuki, A. (1984). Isolation of ophiobolin A and its analogues as inhibitor to photosynthesis. Agricultural and Biological Chemistry 48: 803–805.

    Article  CAS  Google Scholar 

  18. Lim, C.-H., Miyagawa, H., Tsurushima, T., Ueno, T. and Sato, M. (1996). Cochlioquinol: a new cochlioquinone derivative produced by the plant fungus Bipolaris cynodontis. Bioscience, Biotechnology and Biochemistry 60: 724–725.

    Article  CAS  Google Scholar 

  19. Lipski, K. M., McQuiggan, J. D., Loucy, K. J. and Fondy, T. P. (1987). Cytochalasin B: preparation, analysis in tissue extracts and pharmacokinetics after intraperiteneal bolus administration in mice. Analytical Biochemistry 161: 332–340.

    Article  PubMed  CAS  Google Scholar 

  20. Miyagawa, H., Nagai, S., Tsurushima, T., Sato, M. and Ueno, T. (1994). Phytotoxins produced by the plant pathogenic fungus Bipolaris bicolor EI-I. Bioscience, Biotechnology and Biochemistry 58: 1143–1145.

    Article  CAS  Google Scholar 

  21. Nakajima, H., unpublished data.

    Google Scholar 

  22. Nakajima, H., Fujimoto, H., Kimura, Y. and Hamasaki, T. (1993). Importance of ketone function for the phytotoxicity of spiciferone A, a phytotoxin produced by the fungus Cochliobolus spicifer. Bioscience, Biotechnology and Biochemistry 57: 1938–1939.

    Article  CAS  Google Scholar 

  23. Nakajima, H., Fujimoto, H., Matsumoto, R. and Hamasaki, T. (1993). Biosynthesis of spiciferone A and spicifenin. Bioactive metabolites of phytopathogenic fungus, Cochliobolus spicifer. Journal of Organic Chemistry 58: 4526–4528.

    Article  CAS  Google Scholar 

  24. Nakajima, H., Fukuyama, K., Fujimoto, H., Baba, T. and Hamasaki, T. (1994). Absolute stereochemistry of spiciferones and spicifinin, bioactve metabolites of the fungus Cochliobolus spicifer. Journal of Chemical Society, Perkin Transaction 1: 1865–1869.

    Article  Google Scholar 

  25. Nakajima, H., Hamasaki, T., Kohno, M. and Kimura, Y. (1991). Spiciferon B and C, minor phytotoxin from the fungus, Cochliobolus spicifer. Phytochemistry 30: 2563–2565.

    Article  CAS  Google Scholar 

  26. Nakajima, H., Hamasaki, T., Maeta, S., Kimura, Y. and Takeuchi, Y. (1990). A plant growth regulator produced by the fungus, Cochliobolus spicifer. Phytochemistry 29: 1739–1743.

    Article  CAS  Google Scholar 

  27. Nakajima, H., Hamasaki, T. and Kimura, Y. (1989). Structure of speciferone A, a novel y-pyrone plant growth inhibitor produced by fungus Cochliobolus specifer Nelson. Agricultural and Biological Chemistry 53: 2297–2299.

    Article  CAS  Google Scholar 

  28. Nakajima, H., Isomi, K., Hamasaki, T. and Ichinoe, M. (1994). Sorokinianin: a novel phytotoxin produced by phytopathogenic fungus Bipolaris sorokiniana. Tetrahedron Letters 35: 9597–9600.

    Article  CAS  Google Scholar 

  29. Nakajima, H., Kimura, Y. and Hamasaki, T. (1992).. Speciferone, an azaphilone phytotoxin produced by the fungus Cochliobolus specifer. Phytochemistry 31: 105–107.

    Article  CAS  Google Scholar 

  30. Nakajima, H., Matsumoto, R., Mimura, Y. and Hamasaki, T. (1992). Biosynthesis of spicifernin, a unique metabolite of the phytopathogenic fungus, Cochliobolus spicifer. Journal of Chemical Society Chemical Communication 1654–1656.

    Google Scholar 

  31. Nisson, P., Accession, H., Jansson, H. B. and Odham, G. (1993). Production and release of the phytotoxin prehelminthosporol by Bipolaris sorokiniana during growth. FEMS Microbiological Ecology 102: 91–98,.

    Article  Google Scholar 

  32. Nukina, M., Ikeda, M. and Sassa, T. (1980). Two new pyrenolides, fungal morphogenic substances produced by Pyrenophora teres (Diedicke) Drechsler. Agricultural and Biological Chemistry 44: 2761–2762.

    Article  CAS  Google Scholar 

  33. Nukina, M., and Marumo, S. (1977). Radicinol: a new metabolite of Cochliobolus lunuta and absolute stereochemistry of radicinin. Tetrahedron Letters 18: 3271–3272.

    Article  Google Scholar 

  34. Ogawara, H., Higashi, K., Machida, T., Takashima, J., Chiba, N. and Mikawa, T. (1994). Inhibitors of diacylglycerol kinase from Drechslera sacchari. Journal of Antibiotics 47: 499–501.

    Article  PubMed  CAS  Google Scholar 

  35. Pena-Rodriguez, L. M., Armingeon, N. A. and Chilton, W. S. (1988). Toxins from weed pathogens. I. Phytotoxins from Bipolaris pathogen of Johnson grass. Journal of Natural Products 51: 821–828.

    Article  PubMed  CAS  Google Scholar 

  36. Pena-Rodriguez, L. M. and Chilton, W. S. (1989). 3-Anhydroophiobolin A and 3-anhydro-6-O-ophiobolin A, phytotoxic metabolites of the Johnson grass pathogen Bipolaris sorghicola. Journal of Natural Products 52: 1170–1172.

    Article  CAS  Google Scholar 

  37. Pena-Rodriguez L. M. and Chilton, W. S. (1989). Victoxinin and prehelminthosporolactone, two major phytotoxic metabolites produced by Bipolaris sp., a pathogen of Johnson grass. Journal of Natural Products 52: 899–901.

    Article  CAS  Google Scholar 

  38. Park, A. H., Stierle, A. C. and Strobel, G. A. (1994). Metabolism of maculosin, a host specific phytotoxin produced by Alternaria alternata on spotted knapweed (Centaura maculosa). Phytochemistry 35: 101–106.

    Article  CAS  Google Scholar 

  39. Park, A. H. and Strobel, G. A. (1994). Cellular protein receptors of maculosin, a host specific phytotoxin of spotted knapweed (Centaura maculosa). Biochimica et Biophysica Acta 1199: 13–19.

    Article  PubMed  CAS  Google Scholar 

  40. Robeson, D. J. and Strobel, G. (1982). Monocerin, a phytotoxin from Exserohilum turticum (=Drechslera turticum). Agricultural and Biological Chemistry 46: 2681–2683.

    Article  CAS  Google Scholar 

  41. Scott, F. E., Simpson, L. A., Trimble, L. A. and Vederas, J. C. (1984). Biosynthesis of monocerin. Incorporation of 2H-, 13C- and 18O-labeled acetates by Drechslera ravenelii. Journal of Chemical Society, Chemical Communication: 756–758.

    Google Scholar 

  42. Stiele, A. C., Cardellina II, J. H., and Strobel, G. A. (1988). Maculosin, a host specific phytotoxin for spotted knapweed (Centaureaa maculosa). Proceedings of National Academy of Science, U. S. A. 85: 8008–8011.

    Article  Google Scholar 

  43. Strobel, G., Sugawara, F. and Clardy, J. (1987). Phytotoxins from plant pathogens of weedy plants. In Allelochemicals: Role in Agriculture and Forestry, (Ed., G.R. Waller). ACS Symposium Series 330: pp. 516–523. Washington DC: American Chemical Society.

    Chapter  Google Scholar 

  44. Strobel, G., Sugawara, F. and Hershenhom, J. (1992). Pathogens and other products affecting weedy plants. Phytoparasitica 20: 307–323.

    Article  Google Scholar 

  45. Sugawara, F., Hallock, Y. F., Bunkers, G., Kenfield, D. S., Strobel, G. and Yoshida, S. (1993). Phytoactive eremophilanes produced by the weed pathogen Drechslera gigantea. Bioscience, Biotechnology and Biochemistry 57: 236–239.

    Article  CAS  Google Scholar 

  46. Sugawara, F., Kim, K., Kobayashi, K., Uzawa, J., Yoshida, S., Murofushi, A., Takahashi, N. and Strobel, G. (1992). Zearalenone derivatives produced by Drechslera portulacae. Phytochemistry 31: 1987–1990.

    Article  CAS  Google Scholar 

  47. Sugawara, F. and Strobel, G. (1986). (-)-Dihydropyrenophorin, a novel and selective phytotoxin produced by Drechslera avenae. Plant Science 43: 1–5.

    Article  CAS  Google Scholar 

  48. Sugawara, F. and Strobel, G. (1987). Tryptophol, a phytotoxic metabolite of Helminthosporium nodulosum on weedy plants. Phytochemistry 26: 1349–1351.

    Article  CAS  Google Scholar 

  49. Sugawara, F., Strobel, G., Fisher, L. F., Van Duyne, G. D. and Clardy, J. (1985). Bipolaroxin, a selective phytotoxin produced by Bipolaris cynodontis. Proceedings of National Academy of Science U. S. A. 82: 8291–8294.

    Article  CAS  Google Scholar 

  50. Sugawara, F., Strobel, G., Strange, R. N., Siedow, J. N., Van Duyne, G. D. and Clardy, J. (1987). Phytotoxins from the pathogenic fungi Drechslera maydis and Drechslera sorghicola. Proceedings of National Academy of Science U. S. A. 84: 3081–3085.

    Article  CAS  Google Scholar 

  51. Sugawara, K., Sugawara, F., Strobel, G., Fu, Y., Cun-Heng, H. and Clardy, J. (1985). Exserohilone, a novel phytotoxin produced by Exserohilum holmii. Journal of Organic Chemistry 50: 5631–5933.

    Article  CAS  Google Scholar 

  52. Sugawara, F., Takahashi, N., Strobel, G., Strobel, S., Liu, H. S. M. and Clardy, J. (1988). Triticones A and B, novel phytotoxins from the plant pathogenic fungus Drechslera tritici-repentis. Journal of American Chemistry Society 110: 4086.

    Article  CAS  Google Scholar 

  53. Sugawara, F., Takahashi, N., Strobel, G., Yun, C. H., Gray, G., Fu, Y. and Clardy, J. (1988). Some new phytotoxic ophiobolins produced by Drechslera oryzae. Journal of Organic Chemistry 53: 2170–2172.

    Article  CAS  Google Scholar 

  54. Ueda, K., Xiao, J. Z., Doke, N. and Nakatsuka, S. (1992). Structure of BZR-cotoxin II produced by Bipolaris zeicola race 3, the cause of leaf spot disease in corn. Tetrahedron Letter. 33: 5377–5380.

    Article  CAS  Google Scholar 

  55. Ueda, K., Xiao, J. Z., Doke, N. and Nakatsuka, S. (1994). Structure of BZR-cotoxin I produced by Bipolaris zeicola race 3, the cause of leaf spot disease in corn. Tetrahedron Letters 35: 7033–7036.

    Article  CAS  Google Scholar 

  56. Ueda, K., Xiao, J. Z., Doke, N. and Nakatsuka, S. (1995). Isolation and structure of BZR-cotoxin IV produced by Bipolaris zeicola race 3, the cause of leaf spot disease in corn. Tetrahedron Letters 36: 741–743.

    Article  CAS  Google Scholar 

  57. Xiao, J. Z., Tsuda, M., Doke, N. and Nishimura, S. (1991). Phytotoxins produced in spores of Bipolaris oryzae. Phytopathology 81: 58–64.

    Article  CAS  Google Scholar 

  58. Yun, C. H., Sugawara, F. and Strobel, G. A. (1988). The phytotoxic ophiobolins produced by Drechslera oryzae, their structures and biological activity on rice. Plant Science 54: 237–243.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2000 Springer Science+Business Media Dordrecht

About this chapter

Cite this chapter

Sugawara, F. (2000). Phytotoxins as potential herbicides. In: Narwal, S.S., Hoagland, R.E., Dilday, R.H., Reigosa, M.J. (eds) Allelopathy in Ecological Agriculture and Forestry. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-4173-4_8

Download citation

  • DOI: https://doi.org/10.1007/978-94-011-4173-4_8

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-94-010-5817-9

  • Online ISBN: 978-94-011-4173-4

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics