Abstract
Two phytotoxic compounds [2,4-dihydroxy-1,4(2H)-benzoxazin-3-one (DIBOA) and 2(3H)-benzoxazolinone (BOA)] were previously isolated and identified in 35-day-old greenhouse-grown rye shoot tissue. Both compounds were also detected by TLC in greenhouse-grown root and fieldgrown shoot tissue. The concentration of DIBOA varied in the tissues, with the greatest quantity detected in greenhouse-grown shoots. DIBOA and BOA were compared with β-phenyllactic acid (PLA) and β-hydroxybutyric acid (HBA) for activity on seed germination and seedling growth and were consistently more toxic than either compound. Dicot species tested, including lettuce (Lactuca sativa L.), tomato (Lycopersicon esculentum Mill.), and redroot pigweed (Amaranthus retroflexus L.), were 30% more sensitive than the monocots tested. Of the two benzoxazinone compounds, DIBOA was most toxic to seedling growth. DIBOA and BOA reduced chlorophyll production inChlamydomonas rheinhardtii Dangeard, by 50% at 7.5 × 10−5 M and 1.0 × 10−3 M, respectively. Both DIBOA and BOA inhibited emergence of barnyardgrass (Echinochloa crusgalli L. Beauv.), cress (Lepidium sativum L.), and lettuce when applied to soil, indicating their potential for allelopathic activity.
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References
Arqandona, V.H., Luza, J., Niemeyer, H.M., andCorcuera, L.J. 1980. Role of hydroxamic acids in the resistance of cereals to aphids.Phytochemistry 19:1665–1668.
Argandona, V.H., Niemeyer, H.M., andCorcuera, L.J. 1981. Effect of content and distribution of hydroxamic acids in wheat on infestation by the aphidSchizaphis graminum.Phytochemistry 20:673–676.
Barnes, J.P. 1981. Exploitation of rye (Secale cereale L.) and its residues for weed suppression in vegetable cropping systems. MS thesis, Michigan State University, East Lansing. 128 pp.
Barnes, J.P., andPutnam, A.R. 1983. Rye residues contribute weed suppression in no-till cropping systems.J. Chem. Ecol. 9:1045–1057.
Barnes, J.P., andPutnam, A.R. 1985. Evidence for allelopathy by residues and aqueous extracts of rye (Secale cereale).Weed Sci. 34:384–390.
Barnes, J.P.,Putnam, A.R., andBurke, B.A. 1987. Isolation and characterization of allelochemicals in rye (Secale cereale L.) shoot tissue.Phytochemistry. In press.
Beck, S.D., andReese, J.C. 1976. Insect-Plant Interactions: Nutrition and metabolism, pp. 41–92,in J.W. Wallace and R.L. Mansell (eds.). Recent Advances in Phytochemistry. Vol. 10, Biochemical Interactions between Plants and Insects. Plenum Press, New York.
Benoit, R.E., Willits, N.A., andHanna, W.J. 1962. Effect of rye winter cover crop on soil structure.Agron. J. 54:419.
Blevins, R.L., Cook, D., Phillips, S.H., andPhillips, R.E. 1971. Influence of no-tillage on soil moisture.Agron. J. 63:593–596.
Chou, C.-H., andPatrick, Z.A. 1976. Identification and phytotoxic activity of compounds produced during decomposition of corn and rye residues in soil.J. Chem. Ecol. 2:369–387.
Corcuera, L.J., Woodward, M.D., Helgeson, J.P., Kelman, A., andUpper, C.D. 1978. 2,4-Dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one, an inhibitor fromZea mays with differential activity against soft rottingErwinia species.Plant. Physiol. 61:791–795.
Cubbon, M.H. 1925. Effect of a rye crop on the growth of grapes.J. Am. Soc. Agron. 17:568–577.
Fuerst, E.P., andPutnam, A.R. 1983. Separating the competitive and allelopathic components of interference: Theoretical principles.J. Chem. Ecol. 9:937–944.
Hamilton, R.H. 1964. Tolerance of several grass species to 2-chloro-s-triazine herbicides in relation to degradation and content of benzoxazinone derivatives.J. Agric. Food Chem. 12:14–17.
Harborne, J.B. 1977. Introduction to Ecological Biochemistry. Academic Press, London. 243 pp.
Hess, F.D. 1980. AChlamydomonas algal bioassay for detecting growth inhibition herbicides.Weed Sci. 28:515–520.
Hill, H.H. 1926. Decomposition of organic matter in soil.J. Agric. Res. 33:77–99.
Hofman, J., andHofmanova, O. 1969. 1,4-benzoxazine derivatives in plants: Sephadex fractionation and identification of a new glycoside.J. Biochem. 8:109–112.
Kimber, R.W. 1973. II. The effect of rotting of straw from some grasses and legumes on the growth of wheat seedlings.Plant Soil 38:347–361.
Lewin, R. 1984. How microorganisms transport iron.Science 225:401–402.
Long, B.J., Dunn, G.M., andRoutley, D.G. 1974. Rapid procedure for estimating cyclic hydroxamate (DIMBOA) conc, in maize.Crop Sci. 14:601–603.
Lovett, J.V. 1982. Allelopathy and self-defence in plants.Aust. Weeds 2:33–36.
Moreland, D.E., andHill, K.L. 1963. Inhibition of photochemical activity of isolated chloroplasts by polycyclic ureas.Weeds 11:284–287.
Muller, C.H. 1966. The role of chemical inhibition (Allelopathy) in vegetational composition.Bull. Torrey Bot. Club 93:332–351.
Nuttonson, M.Y. 1958. Rye-climate relationships on the use of phenology in ascertaining the thermal and photothermal requirements of rye.Am. Inst. Crop Ecol. 21:219 pp.
Osvald, H. 1953. On antagonism between plants, pp. 167–171,in Osvald, H. and Aberg, E. (eds.). Proceedings of the 7th International Botany Congress, Stockholm, 1950. Almquist and Wiksell, Stockholm.
Overland, L. 1966. The role of allelopathic substances in the “smother crop” barley.Am. J. Bot. 53:423–432.
Patrick, Z.A. 1971. Phytotoxic substances associated with the decomposition in soil of plant residues.Soil Sci. 11:13–18.
Patrick, Z.A., andKoch, L.W. 1958. Inhibition of respiration, germination, and growth of substances arising during the decomposition of certain plant residues in the soil.Can. J. Bot. 36:621–647.
Putnam, A.R., andDefrank, J. 1982. Use of phytotoxic plant residues for selective weed control.Crop Protection 2:173–181.
Putnam, A.R., DeFrank, J., andBarnes, J.P. 1983. Exploitation of allelopathy for weed control in annual and perennial cropping systems.J. Chem. Ecol. 9:1001–1009.
Queirolo, C.B., Andreo, C.S., Vallejos, R.H., Niemeyer, H.M., andCorcuera, L.J. 1981. Effects of hydroxamic acids isolated from Gramineae on adenosine 5′-triphophate synthesis in chloroplasts.Plant Physiol. 68:941–943.
Rice, E.L. 1974.Allelopathy. Academic Press, New York. 353 pp.
Shilling, D.G., Liebl, R.A., andWorsham, A.D. 1985. Rye (Secale cereale L.) and wheat (Triticum aestivum L.) mulch: The suppression of certain broadleaf weeds and the isolation and identification of phytotoxins, pp. 243–271,in A.C. Thompson (ed.). The Chemistry of Allelopathy. American Chemical Society, Washington, DC.
Sillen, L.G., andMartell, A.E. 1964. Stability Constants of Metal Iron Complexes, 2nd ed. The Chemical Society, London.
Sullivan, S.L., Gracen, V.E., andOrtega, A. 1974. Resistance of exotic maize varieties to the European corn borerOstrinia nubilalis (Hubner).Environ. Entomol. 3:718–720.
Swain, T. 1977. Secondary compounds as protective agents.Annu. Rev. Plant Physiol. 28:479–501.
Tipton, C.L., andBuell, E.L. 1970. Ferric iron complexes of hydroxamic acids from maize.Phytochemistry 9:1215–1217.
Waid, J.S. 1975. Hydroxamic acids in soil systems, pp. 65–101,in Paul, E.P., and McLaren, A.D. (eds.). Soil Biochemistry. Marcel Dekker, New York.
Whittaker, R.H., andFeeny, P.P. 1971. Allelochemics: Chemical interaction between species.Science 171:757–770.
Woodword, M.D., Corcuera, L.J., Schnoes, H.K., Helgeson, J.P., andUpper, C.D. 1979. Identification of 1,4-benzoxazin-3-ones in maize extracts by GLC and MS.Plant Physiol. 63:9–13.
Zuniga, G.E., Argandona, V.H., Niemeyer, H.M., andCorcuera, L.D. 1983. Hydroxamic acid content in wild and cultivated Gramineae.Phytochemistry 22:2665–2668.
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Journal Article No. 11945 of the Michigan Agricultural Experiment Station.
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Barnes, J.P., Putnam, A.R. Role of benzoxazinones in allelopathy by rye (Secale cereale L.). J Chem Ecol 13, 889–906 (1987). https://doi.org/10.1007/BF01020168
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DOI: https://doi.org/10.1007/BF01020168