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Benzoxazinones: Cyclic hydroxamic acids found in plants

  • John I. Willard
  • Donald Penner
Part of the Residue Reviews book series (RECT, volume 64)

Abstract

The benzoxazinones are naturally occurring cyclic hydroxamic acids found in numerous plant species. Their possible role in insect and disease resistance, and detoxication of the triazine herbicides, has aroused scientific interest in several disciplines.

Keywords

Stem Rust European Corn Borer Triazine Herbicide Northern Corn Leaf Blight Corn Line 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. Ashford, A. E., and M. E. McCully: Histochemical localization of ß-glycosidases in roots of Zea mays. Protoplasma 77, 411 (1973).CrossRefGoogle Scholar
  2. Barba, R. C., and R. R. Romanowskr, JR.: Differential phytotoxicity of atrazine and ametryne to bananas. Weed Res. 9, 114 (1969).CrossRefGoogle Scholar
  3. Beck, S. D.: Resistance of plants to insects. Ann. Rev. Entomol. 10, 207 (1965).Google Scholar
  4. Beck, S. D., E. T. Kaske, and E. E. Smissman: Quantitative estimation of the resistance factor, 6-methoxybenzoxazolinone, in corn plant tissue. J. Agr. Food Chem. 5, 933 (1957).CrossRefGoogle Scholar
  5. Bemiller, J. N., and A. J. Pappelis: 2,4-Dihydroxy-7-methoxy-1,4-benzoxazin-3-one glucoside in corn. I. Relation of water-soluble, I-butanol-soluble glycoside fraction content of pith cores and stalk rot resistance. Phytopathol. 55, 1237 (1965).Google Scholar
  6. Calus, A. G., G. M. Dunn, D. G. Routley, and R. M. Couture: Genetic and environmental effects on production of inhibitory compounds in corn resistant to Helminthosporium turcicum. Crop Sci. 14, 359 (1974).CrossRefGoogle Scholar
  7. Couture, R. M., D. G. Routley, and G. M. Dunn: Role of cyclic hydroxamic acids in monogenic resistance of maize to Helminthosporium turcicum. Physiol. Plant. Pathol. 1, 515 (1971).CrossRefGoogle Scholar
  8. Dabler, J. M., A. J. Pappelis, and J. N. Bemiller: Effect of phenolic acids and corn extracts upon spore germination of Diplodia zeae. Phytopathol. 59, 1098 (1969).Google Scholar
  9. Elnaghy, M. A., and P. Linko: The role of 4–0-glucosyl-2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one in resistance of wheat to stem rust. Physiol. Plant. 15, 764 (1962).CrossRefGoogle Scholar
  10. Elnaghy, M. A., and M. Shaw: Correlation between resistance to stem rust and the concentration of glucoside in wheat. Nature 210, 417 (1966).CrossRefGoogle Scholar
  11. Gahagan, H. E., and R. O. Mumma: The isolation of 2-(2-hydroxy-7-methoxy-1,4benzoxazin-3-one)ß-D-glucopyranoside from Zea mays. Phytochem. 6, 1441 (1967).CrossRefGoogle Scholar
  12. Gallun, R. L., K. J. Starxs, and W. D. Guthrie: Plant resistance to insects attacking cereals. Ann. Rev. Entomol. 20, 337 (1975).CrossRefGoogle Scholar
  13. Hamilton, R. H.: Tolerance of several grass species to 2-chloro-s-triazine herbicides in relation to degradation and content of benzoxazinone derivatives. J. Agr. Food Chem. 12, 14 (1964).CrossRefGoogle Scholar
  14. Hamilton, R. H., and D. E. Moreland: Simazine: Degradation by corn seedlings. Science 135, 373 (1961).CrossRefGoogle Scholar
  15. Hamilton, R. H., R. S. Bandurski, and W. H. Reusch: Isolation and characterization of cylic hyroxamate from Zea mays. Cereal Chem. 39, 107 (1962).Google Scholar
  16. Hieta, P. K., and A. I. Virtanen: Precursors of benzoxazolinone in rye plants. II. Precursor I, the glucoside. Acta Chem. Scand. 14, 502 (1960).CrossRefGoogle Scholar
  17. Hofman, J., and O. Hofmanova: 1,4-Benzoxazine derivatives in plants: Sephadex fractionation and identification of a new glucoside. European J. Biochem. 8, 109 (1969).CrossRefGoogle Scholar
  18. Hofman, J., and O. Hofmanova: 1,4-Benzoxazine derivatives in plants: Absence of 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3 (4H) -one from uninjured Zea mays plants. Phytochem. 10, 1441 (1971).CrossRefGoogle Scholar
  19. Honkanen, E., and A. I. Virtanen: On the reaction of 2,4-dihydroxy-1,4-benzoxazin-3-one to 2(3) -benzoxazolinone. Acta Chem. Scand. 15, 221 (1961).CrossRefGoogle Scholar
  20. Hurter, J.: Abbauprodukte von Simazine in Gramineen. Experientia 22, 741 (1966).CrossRefGoogle Scholar
  21. Ingham, J. L.: Phytoalexins and other natural products as factors in plant disease resistance. The Bot. Rev. 38, 343 (1972).CrossRefGoogle Scholar
  22. Klun, J. A., and T. A. Brindley: Role of 6-methoxy benzoxazolinone in inbred resistance of host plants (Maize) to first-brood larvae of european corn borer. J. Econ. Entomol. 59, 711 (1966).Google Scholar
  23. Klun, J. A., and J. F. Robinson: Concentration of two 1,4-benzoxazinones in dent corn at various stages of development of the plant and its relation to resistance of the host plant to the european corn borer J. Econ. Entomol. 62, 214 (1969).Google Scholar
  24. Klun, J. A., W. D. Guthrie, A. R. Hallauer, and W. A. Russell: Genetic nature of the concentration of 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one and resistance to the european corn borer in a diallele set of eleven maize inbreds. Crop Sci. 10, 87 (1970a).CrossRefGoogle Scholar
  25. Klun, J. A., C. L. Tipton, J. F. Robinson, D. L. Ostrem, and M. Beroza: Isolation and identification of 6,7-dimethoxy-2-benzoxazolinone from dried tissues of Zea mays (L.) and evidence of its cyclic hydroxamic acid precursor. J. Agr. Food Chem. 18, 663 (1970b).CrossRefGoogle Scholar
  26. Klun, J. A., and T. A. Brindley: 2,4-Dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA), an active agent in the resistance of maize to the european corn borer. J. Econ. Entomol. 60, 1529 (1967).Google Scholar
  27. Knott, D. R., and J. Kumar: Tests of the relationship between a specif phenolic glucoside and stem rust resistance in wheat. Physiol. Plant Pathol. 2, 393 (1972).CrossRefGoogle Scholar
  28. Lamoureux, G. L., L. E. Stafford, and R. H. Shimabukuro: Conjugation of 2-chloro-4,6-bis(alkylamino)-s-triazines in higher plants. J. Agr. Food Chem. 20, 1004 (1972).CrossRefGoogle Scholar
  29. Long, B. J., G. M. Dunn, and D. G. Routley: Relationship of hydroxamic acid content (DIMBOA) in maize to resistance to Helminthosporium turcicum. Crop Sci. 15, 333 (1975).CrossRefGoogle Scholar
  30. Loomis, R. S., S. D. Beck, and J. F. Stauffer: The European corn borer, Pyrausta nibilalis (Hubn). and its principal host plant. V. A. chemical study of host plant resistance. Plant Physiol. 32, 379 (1957).Google Scholar
  31. Lund-Hole, K.: Uptake, translocation and metabolism of simazine in Norway Spruce (Picea abies). Weed Res. 9, 142 (1969).CrossRefGoogle Scholar
  32. Mace, M. E.: Histochemistry of beta-glucosidase in isolines of Zea mays susceptible or resistant to Northern Corn Leaf Blight. Phytopathol. 63, 243 (1973).CrossRefGoogle Scholar
  33. Maehr, H.: Antibiotics and other naturally occurring hydroxamic acids and hy-droxamates. Pure & Applied Chem. 28, 603 (1971).CrossRefGoogle Scholar
  34. Maxwell, F. G., J. N. Jenkins, and W. L. Parrot: Influence of constituents of the cotton plant of feeding, oviposition, and development of the boll weevil. J. Econ. Entomol. 60, 1294 (1967).Google Scholar
  35. Maxwell, F. G., J. N. Jenkins, and W. L. Parrot: Review of European corn borer resistance. Adv. Agron. 24, 187 (1972).CrossRefGoogle Scholar
  36. Molot, P. M.: Recherches sur la résistance du maïs à l’Helminthosporiose et aux Fusarioses. II. Ann. Phytopathol. 1, 353 (1969).Google Scholar
  37. Molot, P. M., and P. Anclade: Résistance commune des lignées de mais à L’Helmintho-sporiose (Helminthosporium turcicum Pass.) et à la Pyrale (Ostrinia nubilalis Hbn.) en relation avec la présence d’une substance identifiable à la 6-methoxy-2(3) -benzoxazolinone. Ann. Epiphyties 19, 75 (1968).Google Scholar
  38. Palmer, R. D., and C. O. Groyan: Tolerance of corn lines to atrazine in relation to content of benzoxazinone derivative, 2-glucoside. Weeds 13, 219 (1965).CrossRefGoogle Scholar
  39. Radosevich, S. R., and A. P. Appleby: Studies on the mechanism of resistance to simazine in common groundsel. Weed Sci. 21, 497 (1973).Google Scholar
  40. Roeth, F. W., and T. L. Lavy: Atrazine translocation and metabolism in Sudangrass, sorghum and corn. Weed Sci. 19, 98 (1971).Google Scholar
  41. Shimabuxuro, R. H.: Significance of atrazine dealkylation in root and shoot of pea plants. J. Agr. Food Chem. 15, 557 (1967a).CrossRefGoogle Scholar
  42. Shimabuxuro, R. H.: Atrazine metabolism and herbicidal selectivity. Plant Physiol. 42, 1269 (1967b).CrossRefGoogle Scholar
  43. Shimabuxuro, R. H.: Atrazine metabolism in resistant corn and sorghum. Plant Physiol. 43, 1925 (1968).CrossRefGoogle Scholar
  44. Shimabuxuro, R. H., and H. R. Swanson: Atrazine metabolism in cotton as a basis for intermediate tolerance. Weed Sci. 18, 231 (1970).Google Scholar
  45. Shimabuxuro, R. H., D. S. Frear, H. R. Swanson, and W. C. Walsh: Glutathione conjugation of atrazine. Plant Physiol. 47, 10 (1971).CrossRefGoogle Scholar
  46. Shimabuxuro, R. H.:, R. E. Kadunce, and D. S. Frear: Dealkylation of atrazine in mature pea plants. J. Agr. Food Chem. 14, 392 (1966).CrossRefGoogle Scholar
  47. Sikka, H. C., and D. E. Davis: Absorption, translocation and metabolism of prometryne in cotton and soybean. Weed Sci. 16, 474 (1968).Google Scholar
  48. Smissman, E. E., M. D. Corbett, N. A. Jenny, and O. Kristiansen: Mechanism of the transformation of 2,4-dihydroxy-1,4-benzoxazin-3-ones to 2-hydroxy-2-methyl4-methoxy-1,4-benzoxazin-3-one to 2-benzoxazolinone. J. Org. Chem. 37, 1700 (1972).CrossRefGoogle Scholar
  49. Tipton, C. L., R. R. Husted, and F. H. C. Tsao: Catalysis of simazine hydrolysis by 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one. J. Agr. Food Chem. 19, 484 (1971)CrossRefGoogle Scholar
  50. Tipton, C. L., J. A. Klun, R. R. Husted, and M. D. Pierson: Cyclic hydroxamic acids and related compounds from maize. Isolation and characterization. Biochem. 9, 2866 (1967).Google Scholar
  51. Tipton, C. L., M. C. Wang, F. H. C. Tsao, C. C. L. Tu, and R. R. Husted: Biosynthesis of 1,4-benzoxazin-3-ones in Zea mays. Phytochem. 12, 347 (1973).CrossRefGoogle Scholar
  52. Virtanen, A. I.: Some aspects of factors in the maize plant with toxic effects on insect larvae. Suomen Kemistilehti B. 34, 29 (1961).Google Scholar
  53. Virtanen, A. I., and P. K. Hietala: 2(3)-Benzoxazolinone an anti-fusarium factor in rye seedlings. Acta Chem. Scand. 9, 1543 (1955).CrossRefGoogle Scholar
  54. Virtanen, A. I., and P. K. Hietala: On the structure of the precursors of benzoxazolinone in rye plants. II. Suomen Kemistilehti 32, 252 (1959).Google Scholar
  55. Virtanen, A. I., and P. K. Hietala: Precursors of benzoxazolinone in rye plants I. Precursors II, the aglucone. Acta Chem. Scand. 14, 499 (1960).CrossRefGoogle Scholar
  56. Virtanen, A. I, and O. Wahlroos: Absence of 6-methoxybenzoxazolinone in uninjured maize tissue. J. Pharm. Sci. 52, 713 (1963).PubMedCrossRefGoogle Scholar
  57. Virtanen, A. I., P. K. Hietala, and O. Wahlroos: An antifungal factor in maize and wheat plants. Suomen Kemistilehti B. 29, 143 (1956).Google Scholar
  58. Virtanen, A. I., P. K. Hietala, and O. Wahlroos: Antimicrobial substances in cereals and fodder plants. Arch. Biochem. Biophys. 69, 286 (1957).CrossRefGoogle Scholar
  59. Wamlroos, O., and A. I. Virtanen: The precursors of 6-methoxy-benzoxazolinone in maize and wheat plants, their isolation and some of their properties. Acta Chem. Scand. 13, 1906 (1959).CrossRefGoogle Scholar
  60. Wamlroos, O., and A. I. Virtanen: On the formation of 6-methoxybenzoxazolinone in maize and wheat plants. Suomen Kemistilehti B. 32, 139 (1959).Google Scholar
  61. Walker, J. C., and M. A. Stahmann: Chemical nature of disease resistance in plants. Ann. Rev. Plant Physiol. 6, 351 (1955).CrossRefGoogle Scholar
  62. Whitney, N. J., and G. G. Mortimore: An antifungal substance in the corn plant and its effect on growth of two stalk-rotting fungi. Nature 183, 341 (1959a).PubMedCrossRefGoogle Scholar
  63. Whitney, N. J., and G. G. Mortimore: Isolation of the antifungal substance, 6-methoxy benzoxazolinone from field corn (Zea mays L.) in Canada. Nature 184, 1320 (1959b).PubMedCrossRefGoogle Scholar
  64. Whitney, N. J., and G. G. Mortimore: Effect of 6-methoxy benzoxalinone on the growth of Xanthomonas stewartii (Erw. Smith) Downson and its presence in sweet corn (Zea mays var. saccharata Bailey). Nature 189, 596 (1959c).CrossRefGoogle Scholar
  65. Willard, J. I., D. Penner, and D. H. Smith: Physiological tolerance in cereals to the cereal leaf beetle. Amer. Soc. Agron, Abstr. p. 78 (1974).Google Scholar

Copyright information

© Springer-Verlag New York Inc. 1976

Authors and Affiliations

  • John I. Willard
  • Donald Penner
    • 1
  1. 1.Department of Crop and Soil SciencesMichigan State UniversityEast LansingUSA

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