Abstract
Ethephon (I) is used commercially to prolong the flow of latex from the rubber tree after tapping (Yield stimulation). The compound is applied to the bark in the region of the tapping cut and the effect on latex flow is due to the ethylene released by chemical decomposition, since gaseous ethylene itself is also a very effective stimulant. When14C-I is applied to the bark of a youngHevea seedling, it is absorbed into the plant by processes which appear to be largely non-metabolic. Ethylene formation commences immediately at the site of application, and the gas is quickly translocated throughout the plant. Translocation of I to all parts of the plant also occurs and the accumulation of14C in the bark above the zone of application is greater than that below. Chromatographic analysis has shown that compounds other than I remain in the plant tissue.
Experiments using14C-I have shown that detached leaves are able to convert a considerable proportion of the compound to at least twelve non-volatile acid products. One of these is a conjugate of I with an unidentified material. A major component of the products is 2-hydroxyethylphosphonic acid (II), which is itself converted to a number of compounds in leaves. The application of I to bark from matureHevea, results in the formation of a single substance which is also a conjugate of I. Neither I nor II is effective ininducing the formation of ethylene from endogenous precursors in vegetativeHevea tissue.
Ethylene is poorly metabolized byHevea leaves and the evidence available indicates that it is unlikely that any of the compounds produced from I are metabolites of ethylene.
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References
Abeles, F. B.: Biosynthesis and mechanism of action of ethylene. Ann. Rev. Plant Physiol.23, 259 (1972).
Abeles, F. B.: Ethylene in plant biology. New York: Academic Press (1973).
Abraham, P. D., P. R. Wycherley, and S. W. Pakianathan: Stimulation of latex flow inHevea brasiliensis by 4-amino-3,5,6-trichloropicolinic acid and 2-chloroethanephosphonic acid. J. Rubber Res. Inst. Malaya20, 291 (1968).
Amchem Products Inc.: Technical service data sheet H.96 Ethrel. (1969).
Archer, B. L., B. G. Audley, and N. P. Mann: Decomposition of 2-chloroethylphosphonic acid in stems and leaves ofHevea brasiliensis. Phytochemistry12, 1535 (1973).
Audley, B. G., and B. L. Archer: Decomposition of 2-chloroethylphosphonic acid in aqueous solution: formation of 2-hydroxyethylphosphonic acid. Chem. & Ind. (London) p. 634 (1973).
Berlet, H. H.: Thin-layer chromatography of keto-acid dinitrophenylhydrazones of biological interest. Anal. Biochem.22, 525 (1968).
Bieleski, R. L., and R. E. Young: Extraction and separation of phosphate esters from plant tissues. Anal. Biochem.6, 54 (1963).
Boatman, S.G.: Preliminary physiological studies on the promotion of latex flow by plant growth regulators. J. Rubber Res. Inst. Malaya19, 243 (1966).
Burrows, S., F. S. M. Grylls, and J. S. Harrison: Paper chromatography of phosphoric esters. Nature170, 800 (1952).
Cooke, A. R., and D. I. Randall: 2-Haloethanephosphonic acids as ethylene releasing agents for the induction of flowering in pineapples. Nature218, 974 (1968).
Dickenson, P. B.: Compositions containing plant growth regulants. British Patent 1315131 (1973).
Edgerton, L. J., and A. H. Hatch: Absorption and metabolism of14C(2-chloroethyl) phosphonic acid in apples and cherries. J. Am. Soc. Hort. Sci.97, 112 (1972).
El Hawary, M. F. S., and R. H. S. Thompson: Separation and estimation of blood keto-acids by paper chromatography. Biochem. J.53, 340 (1953).
Field, R. J., and A. J. Peel: The metabolism and radial movement of growth regulators and herbicides in willow stems. New Phytologist70, 743 (1971).
Fritz, C. D., and W. F. Evans: Processes and compositions for the regulation of plant growth. British Patent No. 1194433 (1970).
Gregory, M. J., and G. M. C. Higgins: The solvolytic fragmentation of 2-haloalkylphosphonic acids. J. Chem. Soc. Perkin II, 711 (1974).
Jeffay, H., and J. Alvarez: Liquid scintillation counting of carbon-14. Anal. Chem.33, 612 (1961).
Lavee, S., and Martin, G.C.: Ethephon (1,2-14C- (2-chlorethyl) phosphonic acid) in peach fruits. 2. metabolism. J. Am. Soc. Hort. Sci.99, 100 (1974).
Lougheed, E. C., and E. W. Franklin: Ethylene evolution from 2-chloroethylphosphonic acid under nitrogen atmospheres. Can. J. Plant Sci.50, 586 (1970).
Martin, G. C., H. A. Abdel-Gawad, and R. J. Weaver: The movement and fate of (2-chlorethyl) phosphonic acid in walnut. J. Am. Soc. Hort. Sci.97, 51 (1972).
Pucher, G. W., C. S. Leavenworth, and H. B. Vickery: Determination of starch in plant tissues. Anal. Chem.20, 850 (1948).
Ribaillier, D.: Importance of lutoids in flow of latex: Effect of stimulation. Rev. Gen. Caoutchouc47, 305 (1970).
Southorn, W. A.: Physiology ofHevea (latex flow). J. Rubber Res. Inst. Malaya21, 494 (1969).
Vogt, W.: Synthesis ofΒ-hydroxyethanephosphonic acid. Tetrahedron Letters No. 15., 1281 (1970).
Weaver, R. J., H. A. Abdel-Gawad, and G. C. Martin: Translocation and persistence of 1,2-14C-(2-chloroethyl) phosphonic acid (ethephon) in Thompson seedless grapes. Physiol. Planatarum26, 13 (1972).
Yamaguchi, M., C. W. Chu, and S. F. Young: Fate of14C(2-Chloroethyl) phosphonic acid in summer squash, cucumber and tomato. J. Am. Soc. Hort. Sci.96, 606 (1971).
Young, R. E., H. K. Pratt, and J. B. Biale: Manometric determination of low concentrations of ethylene. Anal. Chem.24, 551 (1952).
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Audley, B.G., Archer, B.L. & Carruthers, I.B. Metabolism of ethephon (2-chloroethylphosphonic acid) and related compounds inHevea Brasiliensis . Arch. Environ. Contam. Toxicol. 4, 183–200 (1976). https://doi.org/10.1007/BF02221023
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DOI: https://doi.org/10.1007/BF02221023