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Allelopathy in Sustainable Agriculture and Forestry pp 63–104Cite as

Allelochemicals in Plants

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Abstract

This chapter presents a brief coverage of a range of common plant allelochemical groups, and includes discussion of their structures, chemistry, distribution, ecology, bioactivity, biosynthesis, allelopathy, and mode of action where known.

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References

  • Angelini, L.G., Carpanese, G., Cioni, P.L., Morelli, I., Macchia, M. and Flamini, G. (2003) Essential oils from Mediterranean Lamiaceae as weed germination inhibitors. J. Agric. Food Chem. 51, 6158–6164.

    Article  PubMed  CAS  Google Scholar 

  • Angus, J.F., Gardner, P.A., Kirkegaard, J.A. and Desmarchelier, J.M. (1994) Biofumigation: isothiocyanates released fromBrassica roots inhibit growth of the take-all fungus. Plant Soil 162, 107–112.

    Article  CAS  Google Scholar 

  • Avers, C.J. and Goodwin, R.H. (1956) Studies on roots IV. Effects of coumarin and scopoletin on the standard root growth pattern of Phleum pratense. Amer. J. Bot. 43, 612–620.

    Article  CAS  Google Scholar 

  • Bais, H.P., Loyola-Vargas, V.M., Flores, H.E. and Vivanco, J.M. (2001) Root-specific metabolism: the biology and biochemistry of underground organs. In Vitro Cell. Dev. Biol. Plant. 37, 730–741.

    Article  CAS  Google Scholar 

  • Bais, H.P., Vepachedu, R., Gilroy, S., Callaway, R.M. and Vivanco, J.M. (2003a) Allelopathy and exotic plant invasion: from molecules and genes to species interactions. Science 301, 1377–1338.

    Google Scholar 

  • Bais, H.P., Walker, T.S., Kennan, A.J., Stermitz, F.R. and Vivanco, J.M. (2003b) Structure-dependent phytotoxicity of catechins and other flavonoids: Flavonoid conversions by cell-free protein extracts of Centaurea maculosa (Spotted knapweed) roots. J. Agric. Food Chem. 51, 897–901.

    Google Scholar 

  • Barnes, J.P. and Putnam, A.R. (1987) Role of benzoxazinones in allelopathy by rye (Secale cereale L.). J. Chem. Ecol. 13, 889–906.

    Article  CAS  Google Scholar 

  • Batish, D.R., Singh, H.P., Kohli, R.K., Saxena, D.B. and Kaur, S. (2002) Allelopathic effects of parthenin against two weedy species, Avena fatua, andBidens pilosa. Environ. Exper. Bot. 47, 149–155.

    Article  CAS  Google Scholar 

  • Belz, R.G. and Hurle, K. (2004) A novel laboratory screening bioassay for crop seedling allelopathy. J. Chem. Ecol. 30, 175–198.

    Article  PubMed  CAS  Google Scholar 

  • Bialy, Z., Oleszek, W., Lewis, J. and Fenwick, G.R. (1990) Allelopathic potential of glucosinolates (mustard oil glycosides) and their degradation products against wheat. Plant Soil 129, 277–281.

    CAS  Google Scholar 

  • Blum, M.S. (2004a) The importance of alkaloid functions. In: Macias, F.A., J.C.G. Galindo, J.M.G. Molinillo and H.G. Cutler (Eds.), Allelopathy: Chemistry and Mode of Action of Allelochemicals. CRC Press, Boca Raton, pp. 163–181.

    Google Scholar 

  • Blum, U. (2004b) Fate of phenolic allelochemicals in soils – the role of soil and rhizosphere microorganisms. In: Macias, F.A., J.C.G. Galindo, J.M.G. Molinillo and H.G. Cutler (Eds.), Allelopathy: Chemistry and Mode of Action of Allelochemicals. CRC Press, Boca Raton, pp. 57–76.

    Google Scholar 

  • Brown, P.D. and Morra, M.J. (1995) Glucosinolate-containing plant tissues as bioherbicides. J. Agric. Food Chem. 43, 3070–3074.

    Article  CAS  Google Scholar 

  • Brown, P.D. and Morra, M.J. (1996) Hydrolysis products of glucosinolates inBrassica napus tissues as inhibitors of seed germination. Plant Soil. 181, 307–316.

    Article  CAS  Google Scholar 

  • Brown, P.D. and Morra, M.J. (1997) Control of soil-borne plant pests using glucosinolate-containing plants. In: L.D. Sparks (Ed.), Advances in Agronomy. Vol. 61, Academic Press, New York, pp. 167–231.

    Google Scholar 

  • Burgos, N.R., Talbert, R.E. and Mattice, J.D. (1999) Cultivar and age differences in the production of allelochemicals by Secale cereale. Weed Sci. 47, 481–485.

    CAS  Google Scholar 

  • Cambier, V., Hance, T. and de Hoffmann, E. (2000) Variation of DIMBOA and related compounds content in relation to the age and plant organ in maize. Phytochemistry 53, 223–229.

    Article  PubMed  CAS  Google Scholar 

  • Charron, C.G. and Sams, C.E. (1999) Inhibition of Pythium ultimum and Rhizoctonia solani by shredded leaves of Brassica species. J. Amer. Soc. Hortic. Sci. 124, 462–467.

    CAS  Google Scholar 

  • Chaves, N., Sosa, T. and Escudero, J.C. (2001) Plant growth inhibiting flavonoids in exudate of Cistus ladanifer and in associated soils. J. Chem. Ecol. 27, 623–631.

    Article  PubMed  CAS  Google Scholar 

  • Chen, S. and Andreasson, E. (2001) Update on glucosinolate metabolism and transport. Plant Physiol. Biochem. 39, 743–758.

    Article  CAS  Google Scholar 

  • Choesin, D.V. and Boerner, R.E.J. (1991) Allyl isothiocyanate release and the allelopathic potential of Brassica napus (Brassicaceae). Amer. J. Bot. 78, 1083–1090.

    Article  CAS  Google Scholar 

  • Copaja, S.V., Nicol, D. and Wratten, S.D. (1999) Accumulation of hydroxamic acids during wheat germination. Phytochemistry 50, 17–24.

    Article  CAS  Google Scholar 

  • Dalton, B.R. (1999). The occurrence and behavior of plant phenolic acids in soil environments and their potential involvement in allelochemical interference interactions: methodological limitations in establishing conclusive proof of allelopathy. In: Inderjit, K.M.M. Dakshini and C.L. Foy (Eds.), Principles and Practices in Plant Ecology: Allelochemical interactions. CRC Press, Boca Raton, pp. 57–74.

    Google Scholar 

  • Davis, E.F. (1928) The toxic principle of Juglans nigra as identified with synthetic juglone, and its toxic effects on tomato and alfalfa plants. Amer. J. Bot. 15, 620.

    Google Scholar 

  • Dayan, F.E., Kagan, I.A. and Rimando, A.M. (2003) Elucidation of the biosynthetic pathway of the allelochemical sorgoleone using retrobiosynthetic NMR analysis. J. Biol. Chem. 278, 28607–28611.

    Article  PubMed  CAS  Google Scholar 

  • Desai, S.R., Kumar, P. and Chilton, W.S. (1996) Indole is an intermediate in the biosynthesis of cyclic hydroxamic acids in maize. Chem. Commun. 1321.

    Google Scholar 

  • Drobnica, L., Kristian, P. and Augustin, J. (1977) The chemistry of the -NCS group. In: Patai S. (Ed.), The Chemistry of Cyanates and Their Thio Derivatives. Part 2. Wiley, New York.

    Google Scholar 

  • Duke, S.O. and Oliva, A. (2004) Mode of action of phytotoxic terpenoids. In: Macias, F.A., J.C.G. Galindo, J.M.G. Molinillo and H.G. Cutler (Eds.), Allelopathy: Chemistry and Mode of Action of Allelochemicals. CRC Press, Boca Raton, pp. 201–216.

    Google Scholar 

  • Duroux, L., Delmotte, F.M., Lancelin, J.M., Keravis, G. and Jay, A.C. (1998) Insight into naphthoquinone metabolism: beta-glucosidase-catalyzed hydrolysis of hydrojuglone beta-D-glucopyranoside. Biochem. J. 333, 275–283.

    PubMed  CAS  Google Scholar 

  • Einhellig, F.A., Schon, M.K. and Rasmussen, J.A. (1982) Synergistic effects of four cinnamic acid compounds on grain sorghum. J. Plant Growth Regul. 1, 251–258.

    Google Scholar 

  • Einhellig, F.A. (1996) Interactions involving allelopathy in cropping systems. Agron. J. 88, 886–893.

    CAS  Google Scholar 

  • Einhellig, F.A. (2004) Mode of allelochemical action of phenolic compounds. In: Macias, F.A., J.C.G. Galindo, J.M.G. Molinillo and H.G. Cutler (Eds.), Allelopathy: Chemistry and Mode of Action of Allelochemicals. CRC Press, Boca Raton, pp. 217–238.

    Google Scholar 

  • Erdie, L., Szabo-Nagy, A. and Laszlavik, M. (1994) Effects of tannin and phenolics on H+ -ATPase activity in plant plasma membrane. J. Plant Physiol. 144, 49.

    Google Scholar 

  • Fahey, J.W., Zalcmann, A.T. and Talalay, P. (2001)The chemical diversity and distribution of glucosinolates and isothiocyanates among plants. Phytochemistry 56, 5–51.

    Article  PubMed  CAS  Google Scholar 

  • Fate, G., Chang, M. and Lynn, D.G. (1990) Control of germination in Striga asiatica: chemistry of spatial definition. Plant Physiol. 93, 201.

    PubMed  CAS  Google Scholar 

  • Feucht, W. and Treutter, D. (1999) The role of flavan-3-ols and proanthocyanidins in plant defense. In: Inderjit, K.M.M. Dakshini, and C.L. Foy (Eds.), Principles and Practices in Plant Ecology: Allelochemical Interactions. CRC Press, Boca Raton, pp. 307–338.

    Google Scholar 

  • Fischer, N.H. (1986) The function of mono and sesquiterpenes as plant germination and growth regulators. In: Putnam A.R. and C.S. Tang (Eds.), The Science of Allelopathy. Wiley-Interscience, New York, pp. 203–218.

    Google Scholar 

  • Fischer, N.H., Weidenhamer, J.D. and Bradow, J.M. (1989) Inhibition and promotion of germination by several sesquiterpenes. J. Chem. Ecol. 15, 1785–1793.

    Article  CAS  Google Scholar 

  • Fischer, N.H. (1991) Plant terpenoids as allelopathic agents. In: Harborne J.B. and F.A. Tomas-Barberan (Eds.), Ecological Chemistry and Biochemistry of Plant Terpenoids. Clarendon Press, Oxford, pp. 377–398.

    Google Scholar 

  • Friebe, A., Roth, U., Kuck, P., Schnabl, H. and Schulz, M. (1997) Effects of 2,4-dihydroxy-1,4-benzoxazin-3-ones on the activity of plasma membrane H+-ATPase. Phytochemistry 44, 979–983.

    Article  CAS  Google Scholar 

  • Friebe, A. (2001) Role of benzoxazinones in cereals. J. Crop Prod. 4, 379–400.

    Article  CAS  Google Scholar 

  • Gagliardo, R.W. and Chilton, W.S. (1992) Soil transformation of 2(3H)-benzoxazolone of rye into phytotoxic 2-amino-3H-phenoxazin-3-one. J. Chem. Ecol. 18, 1683–1690.

    Article  CAS  Google Scholar 

  • Hagin, R.D. (1989) Isolation and identification of 5-hydroxyindole-3-acetic acid and 5-hydroxytryptophan, major allelopathic aglycons in quackgrass (Agropyron repens L. Beauv.). J. Agric. Food Chem. 37, 1143–1149.

    Article  CAS  Google Scholar 

  • Harborne, J.B. (1991) Recent advances in the ecological chemistry of plant terpenoids. In: Harborne, J.B. and F.A. Tomas-Barberan (Eds.), Ecological Chemistry and Biochemistry of Plant Terpenoids. Phytochemical Society of Europe, Proceedings Vol. 31. Clarendon Press, Oxford, pp. 399–426.

    Google Scholar 

  • Hashimoto, Y. and Shudo, K. (1996) Chemistry of biologically active benzoxazinoids. Phytochemistry 43, 551–559.

    Article  PubMed  CAS  Google Scholar 

  • Haughn, G.W., Davin, L., Giblin, M. and Underhill, E.W. (1991) Biochemical genetics of plant secondary metabolites in Arabidopsis thaliana. Plant Physiol. 97, 217–226.

    PubMed  CAS  Google Scholar 

  • Hejl, A.M., Einhellig, F.A. and Rasmussen, J.A. (1993) Effects of juglone on growth, photosynthesis, and respiration. J. Chem. Ecol. 19, 559–568.

    Article  CAS  Google Scholar 

  • Hejl, A.M. and Koster, K.L. (2004) Juglone disrupts root plasma membrane H+-ATPase activity and impairs water uptake, root respiration, and growth in soybean (Glycine max) and corn (Zea mays). J. Chem. Ecol. 30, 453–471.

    Article  PubMed  CAS  Google Scholar 

  • Hogge, L.R., Reed, D.W., Underhill, E.W. and Haughn, G.W. (1988) HPLC separation of glucosinolates from leaves and seeds of Arabidopsis thaliana and their identification using thermospray liquid chromatography/mass spectrometry. J. Chromatogr. 26, 551–556.

    CAS  Google Scholar 

  • Hoult, A.H.C. and Lovett, J.V. (1993) Biologically active secondary metabolites of barley. III. A method for identification and quantification of hordenine and gramine in barley by high-performance liquid chromatography. J. Chem. Ecol. 19, 2245–2254.

    Article  CAS  Google Scholar 

  • Huang, Z., Haig, T., Wu, H., An, M. and Pratley, J. (2003) Correlation between phytotoxicity on annual ryegrass (Lolium rigidum) and production dynamics of allelochemicals within root exudates of an allelopathic wheat. J. Chem. Ecol. 29, 2263–2279.

    Article  PubMed  CAS  Google Scholar 

  • Inderjit and Dakshini, K.M.M. (1995) Quercetin and quercitrin from Pluchea lanceolata and their effect on growth of asparagus bean. In: Inderjit, K.M.M. Dakshini and F.A. Einhellig (Eds.), Allelopathy: Organisms, Processes, and Applications. Washington. ACS Symposium Series 582, pp. 86–93.

    Google Scholar 

  • Inderjit (1996) Plant phenolics in allelopathy. Bot. Rev. 62, 186–202.

    Google Scholar 

  • Inderjit, Cheng, H.H. and Nishimura, H. (1999) Plant phenolics and terpenoids: transformation, degradation, and potential for allelopathic interactions. In: Inderjit, K.M.M. Dakshini and C.L. Foy (Eds.), Principles and Practices in Plant Ecology: Allelochemical Interactions. CRC Press, Boca Raton, pp. 255–266.

    Google Scholar 

  • Inoguchi, M., Ogawa, S., Furukawa, S. and Kondo, H. (2003) Production of an allelopathic polyacetylene in hairy root cultures of goldenrod (Solidago altissima L.). Biosci. Biotechnol. Biochem. 67, 863–868.

    Article  PubMed  CAS  Google Scholar 

  • Inoue, M., Nishimura, H., Li, H.H. and Mizutani, J. (1992) Allelochemicals from Polygonum sachalinense Fr. Schm. (Polygonaceae). J. Chem. Ecol. 18, 1833.

    Article  CAS  Google Scholar 

  • Kagan, I.A., Rimando, A.M. and Dayan, F.E. (2003) Chromatographic separation and in vitro activity of sorgoleone congeners from the roots of Sorghum bicolor. J. Agric. Food Chem. 51, 7589–7595.

    Article  PubMed  CAS  Google Scholar 

  • Kamo, T., Hiradate, S. and Fujii, Y. (2003) First isolation of cyanamide as a possible allelochemical from hairy vetch (Vicia villosa). J. Chem. Ecol. 29, 275–283.

    Article  PubMed  CAS  Google Scholar 

  • Kato-Noguchi, H. (2002a) Isolation of allelopathic substances in rice seedlings. Plant Prod. Sci. 5, 8–10.

    Google Scholar 

  • Kato-Noguchi, H., Ino, T., Sata, N. and Yamamura, S. (2002b) Isolation and identification of potent allelopathic substance in rice root exudates. Physiol. Plant. 115, 401–405.

    Google Scholar 

  • Kato-Noguchi, H. and Ino, T. (2003a) Rice seedlings release allelopathic substances. Biol. Plant. 46, 157–159.

    Google Scholar 

  • Kato-Noguchi, H., Ino, T. and Ichii, M. (2003b) Changes in release of momilactone B into the environment from rice throughout its life cycle. Funct. Plant Biol. 30, 995–997.

    Google Scholar 

  • Kato-Noguchi, H. (2003c) Allelopathic substances in Pueraria thunbergiana. Phytochemistry 63, 577–580.

    Google Scholar 

  • Kato-Noguchi, H. (2003d) Isolation and identification of an allelopathic substance in Pisum sativum. Phytochemistry 62, 1141–1144.

    Google Scholar 

  • Kato-Noguchi, H. (2004) Allelopathic substance in rice root exudates: rediscovery of momilactone B as an allelochemical. J. Plant Physiol. 161, 271–276.

    Article  PubMed  CAS  Google Scholar 

  • Kim, Y.S. and Kil, B.-S. (2001) Allelopathic effects of some volatile substances from the tomato plant. J. Crop Prod. 4, 313–321.

    Article  CAS  Google Scholar 

  • Kobayashi, A., Morimoto, S., Shibata, Y., Yamashita, K. and Numata, M. (1980) C-10 polyacetylenes as allelopathic substances in dominants in early stages of secondary succession. J. Chem. Ecol. 6, 119–131.

    Article  CAS  Google Scholar 

  • Korableva, N.P., Morozova, E.V., Popova, L.V. and Metlinskii, L.V. (1969) Specific growth inhibitors in connection with dormancy and immunity in plants. Dok. Akad. Nauk SSSR. 184, 979–981.

    CAS  Google Scholar 

  • Krishnan, G., Holshauser, D.L. and Nissen, S.J. (1998) Weed control in soybean (Glycine max) with green manure crops. Weed Technol. 12, 97–102.

    Google Scholar 

  • Lam, J., Christensen, L.P., Farch, T. and Thomasen, T. (1992) Acetylenes from the roots of Solidago species. Phytochemistry 31, 4159–4161.

    Article  CAS  Google Scholar 

  • Lee, K.C. and Campbell, R.W. (1969) Nature and occurrence of juglone in Juglans nigra L. Hortic. Sci. 4, 297–298.

    CAS  Google Scholar 

  • Lehman, M.E. and Blum, U. (1999) Evaluation of ferulic acid uptake as a measurement of allelochemical dose: effective concentration. J. Chem. Ecol. 25, 2585–2600.

    Article  CAS  Google Scholar 

  • Levitt, J. and Lovett, J.V. (1984) Activity of allelochemicals of Datura stramonium L. (thornapple) in contrasting soil types. Plant Soil 79, 181–189.

    Article  CAS  Google Scholar 

  • Liu, D.L. and Lovett, J.V. (1993a) Biologically active secondary metabolites of barley. I. Developing techniques and assessing allelopathy in barley. J. Chem. Ecol. 19, 2217–2230.

    Article  CAS  Google Scholar 

  • Liu, D.L., and Lovett, J.V. (1993b) Biologically active secondary metabolites of barley. II. Phytotoxicity of barley allelochemicals. J. Chem. Ecol. 19, 2231–2244.

    Article  CAS  Google Scholar 

  • Lovett, J.V., Levitt, J., Duffield, A.M. and Smith, N.G. (1981) Allelopathic potential of Datura stramonium L. (thornapple). Weed Res. 21, 165–170.

    Article  Google Scholar 

  • Lovett, J.V., Ryuntyu, M.Y. and Liu, D.L. (1989) Allelopathy, chemical communication, and plant defense. J. Chem. Ecol. 15, 1193–1202.

    Article  Google Scholar 

  • Lovett, J.V., Hoult, A.H.C. and Christen, O. (1994) Biologically active secondary metabolites of barley. IV. Hordenine production by different barley lines. J. Chem. Ecol. 20, 1945–1954.

    Article  CAS  Google Scholar 

  • Lovett, J.V. and Hoult, A.H.C. (1995) Allelopathy and self-defense in barley. In: Inderjit, K.M.M. Dakshini and F.A. Einhellig (Eds.), Allelopathy: Organisms, Processes, and Applications. ACS Symposium Series 582, Washington, pp. 172–183.

    Google Scholar 

  • Macias, F.A. (1995) Allelopathy in the search for natural herbicide models. In: Inderjit, K.M.M. Dakshini and F.A. Einhellig (Eds.), Allelopathy: Organisms, Processes, and Applications. ACS Symposium Series 582, Washington, pp. 310–329.

    Google Scholar 

  • Massey, A.B. (1925) Antagonism of walnuts. Phytopathology 15, 773.

    CAS  Google Scholar 

  • Matsuo, A., Nadaya, K., Nakayama, M. and Hayashi, S. (1981) Plant growth inhibitors isolated from the Liverwort, Plagiochila ovalifolia. Nippon Kagaku Kaishi pp. 665–670.

    Google Scholar 

  • Mizutani, J. (1999) Selected allelochemicals. Crit. Rev. Plant Sci. 18, 653–671.

    Article  CAS  Google Scholar 

  • Moreland, D.E. and Novitsky, W.P. (1987) Effects of phenolic acids, coumarins, and flavanoids on isolated chloroplasts and mitochondria. ACS Symposium Series 330, pp. 247–274.

    Article  CAS  Google Scholar 

  • Mucciarelli, M., Camusso, W., Bertea, C.M., Bossi, S. and Maffei, M. (2001) Effect of (+)-pulegone and other oil components of Mentha x piperita on cucumber respiration. Phytochemistry 57, 91–98.

    Article  PubMed  CAS  Google Scholar 

  • Nakano, H., Nakajima, E., Hiradate, S., Fujii, Y., Yamada, K., Shigemori, H. and Hasegawa, K. (2004) Growth inhibitory alkaloids from mesquite (Prosopis juliflora (Sw.) DC.) leaves. Phytochemistry 65, 587–591.

    Article  PubMed  CAS  Google Scholar 

  • Netzley, D.H. and Butler, L.G. (1986) Roots of sorghum exude hydrophobic droplets containing biologically active components. Crop Sci. 26, 776–778.

    Google Scholar 

  • Niemeyer, H.M. (1988) Hydroxamic acids (4-hydroxy-1,4-benzoxazine-3-ones), defense chemicals in the Gramineae. Phytochemistry 27, 3349–3358.

    Article  CAS  Google Scholar 

  • Niemeyer, H.M. and Perez, F.J. (1995) Potential of hydroxamic acids in the control of cereal pests, diseases, and weeds. In: Inderjit, K.M.M. Dakshini and F.A. Einhellig (Eds.), Allelopathy: Organisms, Processes, and Applications. ACS Symposium Series 582, Washington, pp. 260–269.

    Google Scholar 

  • Nishimura, H., Hiramoto, S., Mizutani, J., Noma, Y., Furusaki, A. and Matsumoto, T. (1983) Structure and biological activity of bottrospicatol, a novel monoterpene produced by microbial transformation of (-)-cis-carveol. Agric. Biol. Chem. 47, 2697.

    CAS  Google Scholar 

  • Oleszek, W. (1987) Allelopathic effects of volatiles from some Cruciferae species on lettuce, barnyard grass and wheat growth. Plant Soil. 102, 271–273.

    Article  CAS  Google Scholar 

  • Olofsdotter, M., Rebulanan, M., Madrid, A., Dali, W., Navarez, D. and Olk, D.C. (2002) Why phenolic acids are unlikely primary allelochemicals in rice. J. Chem. Ecol. 28, 229–242.

    Google Scholar 

  • Overland, L. (1966) The role of allelopathic substances in the smother crop barley. Amer. J. Bot. 53, 423–432.

    Article  CAS  Google Scholar 

  • Perez, F.J. (1990) Allelopathic effect of hydroxamic acids from cereals on Avena sativa and Avena fatua. Phytochemistry 29, 773–776.

    Article  CAS  Google Scholar 

  • Petersen, J., Belz, R., Walker, F. and Hurle, K. (2001) Weed suppression by release of isothiocyanates from turnip-rape mulch. Agron. J. 93, 37–43.

    CAS  Google Scholar 

  • Pheto, M. (1993) Occurrence of cyclic hydroxamic acids in the tissues of barnyard grass (Echinochloa cruz-galli /L./P.B.), and their role in allelopathy. Acta Agron. Hungarica 42, 197–202.

    Google Scholar 

  • Podbielkowski, M., Waleza, M., Dobrzynska, K. and Zobel, A.M. (1996) Reaction of coumarin and its derivatives on ultrastructure ATP-ases and acid phosphatases in meristematic cells of Allium cepa roots. Int. J. Pharm. 34, 105.

    Article  Google Scholar 

  • Reynolds, T. (1987) Comparative effects of alicyclic compounds and quinones on inhibition of lettuce fruit germination. Ann. Bot. 60, 215–223.

    CAS  Google Scholar 

  • Rietveld, W.J. (1983) Allelopathic effects of juglone on germination and growth of several herbaceous and woody species. J. Chem. Ecol. 9, 1119–1133.

    Article  Google Scholar 

  • Rimando, A.M., Olofsdotter, M., Dayan, F.E. and Duke, S.O. (2001) Searching for rice allelochemicals: an example of bioassay-guided isolation. Agron. J. 93, 16–20.

    CAS  Google Scholar 

  • Roberts, M.F. and Wink, M. (1998) Introduction (Chapt. 1). In: Alkaloids: Biochemistry, Ecology, and Medicinal Applications. Plenum Press, New York, pp. 1–7.

    Google Scholar 

  • Romagni, J.G., Duke, S.O. and Dayan, F.E. (2000) Inhibition of plant asparagine synthetase by monoterpene cineoles. Plant Physiol. 123, 725–732.

    Article  PubMed  CAS  Google Scholar 

  • Rosa, E.A.S., Heaney, R.K., Fenwick, G.R. and Portas, C.A.M. (1997) Glucosinolates in crop plants. Hort. Rev. 19, 99–215.

    CAS  Google Scholar 

  • Sardari, S., Nishibe, S. and Daneshtalab, M. (2000) Coumarins, the bioactive structures with antifungal property. In: Atta-ur-Rahman (Ed.), Studies in Natural Products Chemistry. Vol. 23. Elsevier Science, Amsterdam, pp. 335–393.

    Google Scholar 

  • Schulz, M., Friebe, A., Kuck, P., Seipel, M. and Schnabl, H. (1994) Allelopathic effects of living quackgrass (Agropyron repens L.). Identification of inhibitory allelochemicals exuded from rhizome borne roots. Appl. Bot. 68, 195–200.

    CAS  Google Scholar 

  • Sicker, D. and Schulz, M. (2002) Benzoxazinones in plants: occurrence, synthetic access, and biological activity. In: Atta-ur-Rahman (Ed.), Bioactive Natural Products. (Part H), Vol. 27. Elsevier Science, Amsterdam, pp. 185–232.

    Google Scholar 

  • Sicker, D., Hao, H. and Schulz, M. (2004) Benzoxazolin-2(3H)-ones – generation, effects and detoxification in the competition among plants. In: Macias, F.A., J.C.G. Galindo, J.M.G. Molinillo and H.G. Cutler (Eds.), Allelopathy: Chemistry and Mode of Action of Allelochemicals. CRC Press, Boca Raton, pp. 77–102.

    Google Scholar 

  • Spencer, G.F., Wolf, R.B. and Weisleder, D. (1984) Germination and growth inhibitory sesquiterpenes from Iva axillaris seeds. J. Nat. Prod. 47, 730–732.

    Article  CAS  Google Scholar 

  • Stevens, K.L. (1986) Polyacetylenes as allelochemicals. In: Putnam A.R. and C.S. Tang (Eds.), The Science of Allelopathy. Wiley, New York, pp. 219–228.

    Google Scholar 

  • Towers, G.H.N. and Wat, C.K. (1978) Biological activity of polyacetylenes. Rev. Latinoam. Quim. 9, 162–170.

    CAS  Google Scholar 

  • Tsao, R. and Eto, M. (1996) Light-activated plant growth inhibitory activity of cis-dehydromatricaria ester, rose bengal and fluoren-9-one on lettuce (Lactuca sativa L.). Chemosphere 32, 1307–1317.

    Article  CAS  Google Scholar 

  • Tsao, R., Yu, Q., Friesen, I., Potter, J. and Chiba, M. (2000) Factors affecting the dissolution and degradation of oriental mustard-derived sinigrin and allyl isothiocyanate in aqueous media. J. Agric. Food Chem. 48, 1898–1902.

    Article  PubMed  CAS  Google Scholar 

  • Vaughn, S.F. and Spencer, G.F. (1993) Volatile monoterpenes as potential parent structures for new herbicides. Weed Sci. 41, 114–119.

    CAS  Google Scholar 

  • Virtanan, A.I. and Hietala, P.K. (1960) Precursors of benzoxazolinone in rye plants: I. Precursor II, the aglucone. Acta Chem. Scand. 14, 499–502.

    Article  Google Scholar 

  • Vokou, D., Douvli, P., Blionis, G.J. and Halley, J.M. (2003) Effects of monoterpenoids, acting alone or in pairs, on seed germination and subsequent seedling growth. J. Chem. Ecol. 29, 2281–2301.

    Article  PubMed  CAS  Google Scholar 

  • Warton, B., Matthiessen, J.N. and Shakelton, M.A. (2001) Glucosinolate content and isothiocyanate evolution – two measures of the biofumigation potential of plants. J. Agric. Food Chem. 49, 5244–5250.

    Article  PubMed  CAS  Google Scholar 

  • Weir, T.L., Bais, H.P. and Vivanco, J.M. (2003) Intraspecific and interspecific interactions mediated by a phytotoxin, (-)-catechin, secreted by the roots of Centaurea maculosa (Spotted knapweed). J. Chem. Ecol. 29, 2397–2412.

    Article  PubMed  CAS  Google Scholar 

  • Weston, L.A. and Czarnota, M.A. (2001) Activity and persistence of sorgoleone, a long-chain hydroquinone produced by Sorghum bicolor. J. Crop Prod. 4, 363–377.

    Article  CAS  Google Scholar 

  • Wieland, I., Kluge, M., Schneider, B., Schmidt, J., Sicker, D. and Schultz, M. (1998) 3β -D-Glucopyranosyl- benzoxazolin-2(3H)-one -a detoxification product of benzoxazolin-2(3H)-one in oat roots. Phytochemistry 49, 719–722.

    Google Scholar 

  • Wilkes, M.A., Marshall, D.R. and Copeland, L. (1999) Hydroxamic acids in cereal roots inhibit the growth of take-all. Soil Biol. Biochem. 31, 1831–1836.

    Article  CAS  Google Scholar 

  • Wink, M. (1983) Inhibition of seed germination by quinolizidine alkaloids. Aspects of allelopathy in Lupinus albus L. Planta 158, 365–368.

    Article  CAS  Google Scholar 

  • Wink, M. (1985) Chemische verteidigung der lupinen: Zur biologischen bedeutung der chinolizidinalkaloide. Plant Syst. Evol. 150, 65–81.

    Article  CAS  Google Scholar 

  • Wink, M. and Latz-Bruning, B. (1995) Allelopathic properties of alkaloids and other natural products: possible modes of action. In: Inderjit, K.M.M. Dakshini, and F.A. Einhellig (Eds.), Allelopathy: Organisms, Processes, and Applications. Amer. Chem. Soc. Symposium Series 582, Washington, pp. 117–126.

    Google Scholar 

  • Wink, M. (1998) Chemical ecology of alkaloids. In: Roberts M.F. and M. Wink (Eds.), Alkaloids: Biochemistry, Ecology, and Medicinal Applications. Plenum Press, New York, pp. 265–300.

    Google Scholar 

  • Wink, M. (2004) Allelochemical properties of Quinolizidine Alkaloids. In: Macias, F.A., J.C.G. Galindo, J.M.G. Molinillo and H.G. Cutler (Eds.), Allelopathy: Chemistry and Mode of Action of Allelochemicals. CRC Press, Boca Raton, pp. 183–200.

    Google Scholar 

  • Wolf, R.B., Spencer, G.F. and Kwolek, W.F. (1984) Inhibition of velvetleaf (Abutilon theophrasti) germination and growth by benzyl isothiocyanate, a natural toxicant. Weed Sci. 32, 612–615.

    CAS  Google Scholar 

  • Wu, H., Haig, T., Pratley, J., Lemerle, D. and An, M. (2000) Distribution and exudation of allelochemicals in wheat Triticum aestivum. J. Chem. Ecol. 26, 2141–2154.

    Article  CAS  Google Scholar 

  • Wu, H., Haig, T., Pratley, J., Lemerle, D. and An, M. (2001a) Allelochemicals in wheat (Triticum aestivum L.): production and exudation of 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one. J. Chem. Ecol. 27, 1691–1700.

    Google Scholar 

  • Wu, H., Pratley, J., Lemerle, D. and Haig, T. (2001b) Allelopathy in wheat (Triticum aestivum). Ann. Appl. Biol. 139, 1–9.

    Google Scholar 

  • Wu, H., Haig, T., Pratley, J., Lemerle, D. and An, M. (2002) Biochemical basis for wheat seedling allelopathy on the suppression of annual ryegrass (Lolium rigidum). J. Agric. Food Chem. 50, 4567–4571.

    Article  PubMed  CAS  Google Scholar 

  • Yu, J.Q. and Matsui, Y. (1993) p-Thiocyanatophenol as a novel allelochemical in exudates from the root of cucumber. Chem. Express. 8, 577–580.

    CAS  Google Scholar 

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  1. E.H. Graham Center for Agricultural Innovation, Charles Sturt University, Wagga Wagga, Australia

    Terry Haig

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  1. Terry Haig
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  1. South China Agricultural University, Guangzhou, Guangdong, China

    Ren Sen Zeng

  2. Lakehead University, Thunder Bay, Ontario, Canada

    Azim U. Mallik

  3. Institute of Tropical & Sub-tropical Ecology, South China Agricultural University, Guangzhou, Guangdong, China

    Shi Ming Luo

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Haig, T. (2008). Allelochemicals in Plants. In: Zeng, R.S., Mallik, A.U., Luo, S.M. (eds) Allelopathy in Sustainable Agriculture and Forestry. Springer, New York, NY. https://doi.org/10.1007/978-0-387-77337-7_4

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