Skip to main content

Phytotoxins as potential herbicides

Abstract

Phytotoxins are produced in various culture media by many fungi that are pathogenic to weeds. These phytotoxins belong to a wide array of chemical substances including sesquiterpenoids, sesterterpenoids, diketopiperazines, peptides, spirocyclic lactams, isocoumarins, and polyketides. In most cases, the phytotoxin belongs to a family of related compounds produced by the fungus. These related compounds may or may not be phytotoxins. Phytotoxin production, in some cases, is optimized by the addition of a host extract to the culture medium. Biological activity is usually observed in a range of concentrations from 10−3 to 10−6 M. The concept of using these molecules, derivatives thereof, or related compounds as herbicides should be explored.

This is a preview of subscription content, access via your institution.

References

  1. 1

    Atkin, C. L., and Neilands, J. B., Leaf infections: Siderochromes (natural polyhydroxamates) mimic the ‘green island’ effect. Science176 (1972) 300–301.

    Google Scholar 

  2. 2

    Berglund, D., Strobel, S., Sugawara, F., and Strobel, G., Flow cytometry as a method for assaying the biological activity of phytotoxins. Plant Sci.56 (1988) 183–188.

    Article  Google Scholar 

  3. 3

    Bohlman, F., and Otto, W., Synthese des Isopetasols. Liebigs Ann. Chem. (1982) 186–190.

  4. 4

    Bunkers, G., PhD Thesis, Montana State University, Bozeman, MT 1989.

  5. 5

    Canales, M. W., and Gray, G. R., 6-Epiophiobolin A and 3-anhydro-6-epiophiobolin A — Host specific phytotoxins ofDrechslera maydis (race T). Phytochemistry27 (1988) 1653–1663.

    Article  Google Scholar 

  6. 6

    Couch, H. B., Diseases of Turfgrasses, p. 10. Reinhold Publishing Corp., New York 1962.

    Google Scholar 

  7. 7

    Cutler, H. G., Isolating, characterizing, and screening mycotoxins for herbicidal activity, in: The Science of Allelopathy, pp. 147–170. Eds A. R. Putnam and C. S. Tang. Wiley-Interscience, New York 1986.

    Google Scholar 

  8. 8

    Dekhuijzen, H. M., Endogenous cytokinins in healthy and diseased plants, in: Physiological Plant Pathology, Encyclopedia of Plant Physiology, N.S., vol. 4, pp. 538–540. Eds R. Heitefuss and P. H. Williams. Springer-Verlag, New York 1976.

    Google Scholar 

  9. 9

    Dhar, T. K., Siddiqui, K., and Ali, E., Structure of phaseolinone, a novel phytotoxin fromMacrophomina phaseolina. Tetrahedron Lett.23 (1982) 5459–5462.

    Google Scholar 

  10. 10

    Dinoor, A., and Eshed, N., The role and importance of pathogens in natural plant communities. A. Rev. Phytopath.22 (1984) 443–466.

    Article  Google Scholar 

  11. 11

    Duke, S. O., Naturally occurring chemical compounds as herbicides. Rev. Weed Sci.2 (1986) 15–44.

    Google Scholar 

  12. 12

    Duke, S. O., Microbially produced phytotoxins as herbicides — a perspective, in: The Science of Allelopathy, pp. 287–304. Eds A. R. Putnam and C. S. Tang. Wiley - Interscience, New York 1986.

    Google Scholar 

  13. 13

    Graniti, A., Durbin, R. D., and Ballio, A. (Eds.), Phytotoxins and Plant Pathogenesis. Springer-Verlag, Berlin 1988.

    Google Scholar 

  14. 14

    Hallock, Y., Clardy, J., Kenfield, D., and Strobel, G., De-O-methyldiaporthin, a new phytotoxin fromDrechslera siccans. Phytochemistry27 (1988) 3123–3125.

    Article  Google Scholar 

  15. 15

    Hallock, Y., PhD thesis. Cornell University, Ithaca, New York 1988.

  16. 16

    Kenfield, D. S., Hallock, Y. F., Clardy, J., and Strobel, G. A., Curvulin andO-methylcurvulinic acid: Phytotoxic metabolites ofDrechslera indica which cause necroses on purslane and spiny amaranth. Plant Sci.60 (1988) 123–127.

    Article  Google Scholar 

  17. 17

    Kenfield, D. S., Bunkers, G., Wu, Ya-Hua, Strobel, G. A., Sugawara, F., Hallock, Y., and Clardy, J., Gigantenone — a novel phytohormone mimic. Experientia45 (1989) 900–902.

    Google Scholar 

  18. 18

    Kenfield, D. S., Strobel, S., Sugawara, F., Berglund, D., and Strobel, G. A., Triticone A, a novel bioactive lactam with potential as a molecular probe. Biochem. biophys. Res. Commun.157 (1988) 174–182.

    Article  PubMed  Google Scholar 

  19. 19

    Lam, A.,Drechslera siccans from ryegrass fields in England and Wales. Trans. Br. Mycol. Soc.83 (1984) 305–311.

    Google Scholar 

  20. 20

    Murray, R. D. H., Mendez, J., and Brown, S. A. (Eds), The Natural Coumarins. Occurrence, Chemistry, and Biochemistry. Wiley, Chichester 1982.

    Google Scholar 

  21. 21

    Oyama, H., Sassa, T., and Ikeda, M., Structures of new plant growth inhibitors,trans- andcis-resorcylides. Agric. biol. Chem.42 (1978) 2408–2409.

    Google Scholar 

  22. 22

    Pinder, A. R., The chemistry of the eremophilane and related sesquiterpenes. Fortschr. Chem. org. Naturst.34 (1977) 81–186.

    Google Scholar 

  23. 23

    Riche, C., Pascard-Billy, C., Devys, M., Gaudemer, A., and Barbier, M., Structure crystalline et moléculaire de la phoménone, phytotoxine produite par le champignonPhoma exigua var.non-oxydabilis. Tetrahedron Lett.32 (1974) 2765–2766.

    Article  Google Scholar 

  24. 24

    Robeson, D. J., and Strobel, G., Zinniol induces chlorophyll retention in barley leaves: the selective action of a non-host-specific phytotoxin. Phytochemistry23 (1984) 1597–1599.

    Article  Google Scholar 

  25. 25

    Stierle, A., Cardellina II, J. H., and Strobel, G., Maculosin, a hostspecific phytotoxin for spotted knapweed fromAlternaria alternata. Proc. natl Acad. Sci. USA85 (1989) 8008–8011.

    Google Scholar 

  26. 26

    Stierle, A., Cardellina, J., and Strobel, G. A., Phytotoxins fromAlternaria alternata a pathogen of spotted knapweed. J. nat. Prod.52 (1989) 42–47.

    Article  Google Scholar 

  27. 27

    Strobel, G., Phytotoxins. A. Rev. Biochem.51 (1982) 309–333.

    Article  Google Scholar 

  28. 28

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

    Google Scholar 

  29. 29

    Strobel, G., Kenfield, D., and Sugawara, F., The incredible fungal genus —Drechslera and its phytotoxic ophiobolins. Phytoparasitica16 (1988) 145–152.

    Google Scholar 

  30. 30

    Sugawara, F., and Strobel, G. A., (-)Dihydropyrenophorin, a novel and selective phytotoxin produced byDrechslera avenae. Plant Sci.43 (1986) 1–5.

    Article  Google Scholar 

  31. 31

    Sugawara, F., Strobel, G., Fisher, L. E., Van Duyne, G. D., and Clardy, J., Bipolaroxin, a selective phytotoxin produced byBipolaris cynodontis. Proc. natl Acad. Sci. USA82 (1985) 8291–8294.

    PubMed  Google Scholar 

  32. 32

    Sugawara, F., Takahashi, N., Strobel, G., Yun, C. H., Gray, G., Fu, Y., and Clardy, J., Some new phytotoxic ophiobolins produced byDrechslera oryzae. J. org. Chem.53 (1988) 2170–2172.

    Article  Google Scholar 

  33. 33

    Sugawara, D., Sugawara, F., Strobel, G. A., Yali Fu, He, Cun-Heng, and Clardy, J., Exserohilone: A novel phytotoxin produced byExserohilum holmii. J. org. Chem.50 (1985) 5631–5633.

    Article  Google Scholar 

  34. 34

    Sugawara, F., Samsoedin, R., Takahashi, N., Liu, H., Fu, Y., Clardy, J., Strobel, S., Berglund, D. L., and Strobel, G., Triticones, novel spirocyclic lactam compounds isolated from the plant pathogenic fungus,Drechslera tritici-repentis. J. Am. chem. Soc.110 (1988) 4086.

    Article  Google Scholar 

  35. 35

    Sugawara, F., Strobel, G., Strange, R., Siedow, J., Van Duyne, G. D., and Clardy, J., Phytotoxins from the pathogenic fungiDrechslera maydis andDrechslera sorghicola. Proc. natl Acad. Sci. USA84 (1987) 3081–3085.

    Google Scholar 

  36. 36

    Sugawara, F., and Strobel, G. A., Tryptophol, a phytotoxin produced byDrechslera nodulosum. Phytochemistry26 (1987) 1349–1351.

    Article  Google Scholar 

  37. 37

    Tanaka, S., Wada, K., Marumo, S., and Hattori, H., Structure of sporogen AO-1, a sporogenic substance. Tetrahedron Lett.25 (1984) 5907–5910.

    Article  Google Scholar 

  38. 38

    Tietjen, K. G., Hunkler, D., and Matern, U., Differential response of cultured parsley cells to elicitors from two nonpathogenic strains of fungi. I. Identification of induced products as coumarin derivatives. Eur. J. Biochem.131 (1983) 409–413.

    Article  PubMed  Google Scholar 

  39. 39

    Wei, R., Schnoes, H. K., Hart, P. A., and Strong, F. M., The structure of PR-toxin, a mycotoxin fromPenicillium roqueforti. Tetrahedron31 (1975) 109–114.

    Article  Google Scholar 

Download references

Author information

Affiliations

Authors

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Strobel, G., Kenfield, D., Bunkers, G. et al. Phytotoxins as potential herbicides. Experientia 47, 819–826 (1991). https://doi.org/10.1007/BF01922462

Download citation

Key words

  • Phytotoxins
  • herbicides
  • weeds
  • fungi
  • Cochliobolus
  • Drechslera
  • Phoma
  • Alternaria