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Mechanisms of adsorption of s-triazines by clay colloids and factors affecting plant availability

  • Conference paper
Single Pesticide Volume: The Triazine Herbicides

Part of the book series: Residue Reviews / Rückstands-Berichte ((RECT,volume 32))

Abstract

Many new organic agricultural chemicals have been developed which offer great potential in the production and preservation of food and fiber (Weber 1969). In the process of developing and utilizing these chemicals we must come to understand how they affect the target organisms and what becomes of them after they have done their job. The purpose of this review is to discuss1 the behavior of one family of these organic compounds, the s-triazines, at the molecular level, in systems in which the chemicals are associated with clay minerals. Factors affecting the adsorption and release of s-triazines by clay colloids and the availability of the compounds to plant roots will also be included. The literature citations are limited to those studies in which s-triazines and clays were directly associated and situations in which other compounds behaved in a manner similar to the s-triazines.

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References

  • Allcock, H. R.: Heteroatom ring systems and polymers. New York: Academic Press (1967).

    Google Scholar 

  • Allis, E. S.: Solvent effects on reaction rates and mechanisms. New York: Academic Press (1966).

    Google Scholar 

  • Armstrong, D. E., and G. Chesters: Properties of protein-bentonite complexes as influenced by equilibration conditions. Soil Sci. 98, 39 (1964).

    Article  CAS  Google Scholar 

  • Armstrong, D. E., and R. F. Harris: Atrazine hydrolysis in soil. Soil Sci. Soc. Amer. Proc. 31, 61 (1967).

    CAS  Google Scholar 

  • Audus, L. J.: The physiology and biochemistry of herbicides. New York: Academic Press (1964).

    Google Scholar 

  • Bailey, G. W., and J. L. White: Review of adsorption and desorption of organic pesticides by soil colloids, with implications concerning pesticide bioactivity. J. Agr. Food Chem. 12, 324 (1964).

    Article  CAS  Google Scholar 

  • Bailey, G. W.: Herbicides—A compilation of their physical, chemical, and biological properties. Residue Reviews 10, 97 (1965).

    PubMed  CAS  Google Scholar 

  • Bailey, G. W., and T. Rothberg: Adsorption of organic herbicides by montmorillonite. Role of pH and chemical character by adsorbate. Soil Sci. Soc. Amer. Proc. 32, 222 (1968).

    CAS  Google Scholar 

  • Bailey, S. W.: The status of clay minerals. Clay and Clay Minerals, 14th Conf., p. 1 (1966).

    Google Scholar 

  • Banin, A., and S. Ravirovitch: Kinetics of reactions in the conversion of Na-or Ca-saturated clays to H-Al clay. Clays and Clay Minerals, 14th Conf., p. 193 (1966).

    Google Scholar 

  • Barshad, I.: The effect of the interlayer cations on the expansion of the mica type of crystal lattice. Amer. Min. 35, 225 (1950).

    CAS  Google Scholar 

  • Boitsov, E. N., and A. I. Finrelshtein: Optical investigations of the molecular structure of s-triazine derivatives. V. Infrared adsorption spectra of salts of oxy-and amino-derivatives of s-triazine. Optics and Spectroscopy 7, 307 (1959).

    Google Scholar 

  • Boitsov, E. N., and V. A. Petukov: Dependence of the vacuum ultraviolet spectra of sym-triazine derivatives on their molecular structure. Optics and Spectroscopy 13, 151 (1962).

    Google Scholar 

  • Burnside, O. C., and R. Behrens: Phytotoxicity of simazine. Weeds 9, 145 (1961).

    Article  Google Scholar 

  • Coleman, N. T., and D. Craig: The spontaneous alteration of hydrogen clay. Soil Sci. 91, 14 (1961).

    Article  CAS  Google Scholar 

  • Cruz, M., J. L. White, and J. D. Russell: Montmorillonite-s-triazine interactions. Israel J. Chem. 6, 315 (1968).

    CAS  Google Scholar 

  • Davies, J. T., and E. K. Rideal: Interfacial phenomena. New York: Academic Press (1963).

    Google Scholar 

  • Day, B. E., L. S. Jordan, and V. A. Jolliffe: The influence of soil characteristics on the adsorption and phytotoxicity of simazine. Weed Sci. 16, 209 (1968).

    CAS  Google Scholar 

  • Dixon, J. K., N. T. Woodrerry, and G. W. Costa: The dissociation constants of melamine and certain of its compounds. J. Amer. Chem. Soc. 69, 599 (1947).

    Article  CAS  Google Scholar 

  • Ekwall, P., K. Grout, and V. Runnstromreio: Surface chemistry. New York: Academic Press (1965).

    Google Scholar 

  • Ensminger, L. E., and J. E. Gieseking: Resistance of clay-adsorbed proteins to proteolytic hydrolysis. Soil Sei. 53, 205 (1942).

    CAS  Google Scholar 

  • Estermann, E. F., G. H. Peterson, and A. D. Mclaren: Digestion of clay-protein, lignin-protein, and silica-protein complexes by enzymes and bacteria. Soil Sci. Soc. Amer. Proc. 23, 31 (1959).

    CAS  Google Scholar 

  • Farmer, V. C., and M. M. Mortland: An infrared study of the coordination of pyridine and water to exchangeable cations in montmorillonite and saponite. J. Chem. Soc. (A), p. 344 (1966).

    Google Scholar 

  • Frank, H. S., and W. Wen: Structural aspects of ion-solvent interaction in aqueous solutions. A suggested picture of water structure. Disc. Faraday Soc. 24, 133 (1957).

    Article  Google Scholar 

  • Freed, V. H., J. Vernetti, and M. Montgomery: The soil behavior of herbicides as influenced by their physical properties. Proc. W. Weed Control Conf. 19, 21 (1962).

    Google Scholar 

  • Fripiat, J. J.: Surface chemistry and soil science. In E. D. Hallsworth and D. V. Crawford (ed.): Experimental pedology, pp. 3–13. London: Butterworths (1965).

    Google Scholar 

  • Frissel, M. J.: The adsorption of some organic compounds, especially herbicides, on clay minerals. Versl. Landbouwk. Onderz. N.R. 67.3, Wageningen, 54 pp. (1961).

    Google Scholar 

  • Frissel, M. J., and G. H. Bolt: Interaction between certain ionizable organic compounds (herbicides) and clay minerals. Soil Sci. 94, 284 (1962).

    Article  CAS  Google Scholar 

  • Futrell, J. H., and T. O. Tiernan: Ion-molecule reactions. Science 162, 415 (1968).

    Article  PubMed  CAS  Google Scholar 

  • Gieseking, J. E.: The clay minerals in soils. Adv. Agron. 1, 159 (1949).

    Article  CAS  Google Scholar 

  • Giles, C. H., T. H. Macewan, S. N. Nakhwa, and D. Smith: Studies in adsorption. Part XI. A system of classification of solution adsorption isotherms, and its use in diagnosis of adsorption mechanisms and in measurement of specific surface areas of solids. J. Chem. Soc., p. 3973 (1960).

    Google Scholar 

  • Gould, R. F.: Organic pesticides in the environment. Adv. Chem. Series 60, 309 (1966).

    Google Scholar 

  • Greenland, D. J.: Interactions between clays and organic compounds in soils. Part I. Mechanisms of interaction between clays and defined organic compounds. Soils and Fert. 28, 415 (1965a).

    Google Scholar 

  • Greenland, D. J.: Interaction between clays and organic compounds in soils. Part II. Adsorption of soil organic compounds and its effect on soil properties. Soils and Fert. 28, 521 (1965b).

    CAS  Google Scholar 

  • Grim, R. E.: Clay Mineralogy. New York: McGraw-Hill (1968).

    Google Scholar 

  • Grover, R.: Influence of organic matter, texture, and available water on the toxicity of simazine in soil. Weeds 14, 148 (1966).

    Article  CAS  Google Scholar 

  • Gysin, H., and E. Knüsli: Chemistry and herbicidal properties of triazine derivatives. Adv. Pest Control Research 3, 289 (1960).

    CAS  Google Scholar 

  • Hance, R. J.: Relationship between partition data and the adsorption of some herbicides by soils. Nature 214, 630 (1967).

    Article  CAS  Google Scholar 

  • Hance, R. J.: Decomposition of herbicides in the soil by non-biological chemical processes. J. Sci. Food Agr. 18, 544 (1967).

    Article  CAS  Google Scholar 

  • Harris, C. I.: Adsorption, movement, and phytotoxicity of monuron and s-triazine herbicides in soil. Weeds 14, 6 (1966).

    Article  CAS  Google Scholar 

  • Harris, C. I.: Fate of 2-chloro-s-triazines in soil. J. Agr. Food Chem. 15, 157 (1967).

    Article  CAS  Google Scholar 

  • Harris, C. I.: Movement of herbicides in soil. Weeds 15, 214 (1967).

    Article  CAS  Google Scholar 

  • Harris, C. I., and T. J. Sheets: Influence of soil properties on adsorption and phytotoxicity of CIPC, diuron, and simazine. Weeds 13, 215 (1965).

    Article  CAS  Google Scholar 

  • Harris, C. I., and G. F. Warren: Adsorption and desorption of herbicides by soil. Weeds 12, 120 (1964).

    Article  Google Scholar 

  • Harter, R. D., and J. L. Ahlrichs: Determination of clay surface acidity by infrared spectroscopy. Soil Sci. Soc. Amer. Proc. 31, 30 (1967).

    CAS  Google Scholar 

  • Hayes, M. H. B.: The role of soil organic matter in the adsorption of triazine herbicides. Residue Reviews, this volume (1969).

    Google Scholar 

  • Hendricks, S. B., R. A. Nelson, and L. T. Alexander: Hyrdation mechanism of the clay mineral montmorillonite saturated with various cations. J. Amer. Chem. Soc. 62, 1457 (1940).

    Article  CAS  Google Scholar 

  • Hirt, R. C., and R. G. Sehmirr: Ultraviolet adsorption spectra of derivatives of symmetric triazine—II. Oxo-triazines and their acyclic analogs. Spectrochimica Acta 12, 127 (1958).

    Article  CAS  Google Scholar 

  • Hirt, R. C., H. L. Strauss, and J. G. Koren: Spectrophotometrically determined ionization constants of derivatives of symmetric triazines. J. Chem. Eng. Data 6, 610 (1961).

    Article  CAS  Google Scholar 

  • Holly, K., and H. A. Roberts: Persistence of phytotoxic residues of triazine herbicides in soil. Weed Research 3, 1 (1963).

    Article  CAS  Google Scholar 

  • Horrobin, S.: The hydrolysis of some chloro-1,3,5-triazines. Mechanism-structure and reactivity. J. Chem. Soc., p. 41–30 (1963).

    Google Scholar 

  • Jackson, M. L.: Structural role of hydronium in layer silicates during soil genesis. Trans. 7th Internat. Congress Soil Sci., p. 445 (1960).

    Google Scholar 

  • Keenan, A. G., R. W. Mooney, and L. A. Wood: The relation between exchangeable ions and water adsorption on kaolinite. J. Phys. Chem. 55, 1462 (1951).

    Article  CAS  Google Scholar 

  • Kipling, J. J.: Adsorption from solutions of non-electrolytes. New York: Academic Press (1965).

    Google Scholar 

  • Kohnke, H.: Soil physics. New York: McGraw-Hill (1968).

    Google Scholar 

  • Kosower, E. M.: Physical organic chemistry. New York: Wiley (1968).

    Google Scholar 

  • Kunze, G. W.: Pesticides and clay minerals. In: Pesticides and their effects on soils and water. A.S.A. Special Publ. No. 8, Madison, Wis., pp. 49–70 (1966).

    Google Scholar 

  • Lailach, G. E., T. D. Thompson, and G. W. Brindley: Adsorption of pyrimidines, purines, and nucleoses by Lidi-, Na-, Mg-, and Ca-montmorillonite. Clays and Clay Minerals, 16th Conf., p. 285 (1968).

    Google Scholar 

  • Laity, T. L.: Micromovement mechanisms of s-triazines in soil. Soil Sei. Soc. Amer. Proc. 32, 377 (1968).

    Google Scholar 

  • Low, P. F.: The role of aluminum in the titration of bentonite. Soil Sci. Soc. Amer. Proc. 19, 135 (1955).

    CAS  Google Scholar 

  • Low, P. F.: Physical chemistry of clay-water interaction. Adv. Agron. 13, 269 (1961).

    Article  CAS  Google Scholar 

  • Low, P. F.: Influence of adsorbed water on exchangeable ion movement. Clays and Clay Minerals, 9th Conf., p. 219 (1962).

    Google Scholar 

  • Marshall, C. E.: The physical chemistry and mineralogy of soils. New York: Wiley (1964).

    Google Scholar 

  • Martin, J. P.: Influence of pesticide residues on soil microbiological and chemical properties. Residue Reviews 4, 96 (1963).

    CAS  Google Scholar 

  • Martin, R. T.: Adsorbed water on clay. A review. Clays and Clay Minerals, 9th Conf., p. 28 (1962).

    Google Scholar 

  • Mathers, A. C., S. B. Weed, and N. T. Coleman: The effect of acid and heat treatment on montmorillonoids. Clays and Clay Minerals, 2d Conf., p. 403 (1954).

    Google Scholar 

  • Mcglamery, M. D., and F. W. Slife: The adsorption and desorption of atrazine as affected by pH, temperature, and concentration. Weeds, 14, 37 (1966).

    Article  Google Scholar 

  • Mclaren, A. D., G. H. Peterson, and I. Barshad: The adsorption and reactions of enzymes and proteins on clay minerals. IV. Kaolinite and montmorillonite. Soil Sci. Soc. Amer. Proc. 22, 239 (1958).

    CAS  Google Scholar 

  • Mering, J.: On the hydration of montmorillonite. Trans. Faraday Soc. 42B, 205 (1946).

    Article  CAS  Google Scholar 

  • Morimoto, G.: Dissociation constants of 6-substituted-diamino-1,3,5-triazines. J. Chem. Soc. Japan 87, 790 (1966a).

    CAS  Google Scholar 

  • Morimoto, G.: Infrared adsorption of 6-substituted-2,4-diamino-1,3,5-triazines. J. Chem. Soc. Japan 87, 797 (1966b).

    CAS  Google Scholar 

  • Mortland, M. M., J. J. Fripiat, J. Chaussidon, and J. Uytterhoeven: Interaction between ammonia and the expanding lattices of montmorillonite and vermiculite. J. Phys. Chem. 67, 248 (1963).

    Article  CAS  Google Scholar 

  • Mysels, K. J.: Introduction to colloid chemistry. New York: Interscience (1964).

    Google Scholar 

  • Nancollas, G. H.: Interactions in electrolyte solutions. New York: Elsevier (1966).

    Google Scholar 

  • Nearpass, D. C.: Effects of soil acidity on the adsorption, penetration, and persistence of simazine. Weeds 13, 341 (1965).

    Article  CAS  Google Scholar 

  • Nearpass, D. C.: Effect of the predominating cation on the adsorption of simazine and atrazine by Bayboro clay soil. Soil Sci. 103, 177 (1967).

    Article  CAS  Google Scholar 

  • Pince, L. A., R. S. Dyal, and F. E. Allison: Protein-montmorillonite complexes, their preparation and the effects of soil micro-organisms on their decomposition. Soil Sci. 78, 109 (1954).

    Article  Google Scholar 

  • Pince, L. A., A. Soulides, and F. E. Allison: Antibiotics in soils. II. Extent and mechanism of release. Soil Sci. 91, 94 (1961).

    Article  Google Scholar 

  • Ross, M.: The torbenite minerals as model compounds for the hydrous layer silicates. Clays and Clay Minerals, 13th Conf., p. 65 (1966).

    Google Scholar 

  • Russell, J. D., M. I. Cruz, and J. L. White: The adsorption of 3-aminotriazole by montmorillonite. J. Agr. Food Chem. 16, 21 (1968a).

    Article  CAS  Google Scholar 

  • Russell, J. D., G. W. Bailey, W. R. Payne, J. D. Pope, and J. I. Teasley: Mode of chemical degradation of s-triazines by montmorillonite. Science 160, 3140 (1968b).

    Article  Google Scholar 

  • Scott, D. C., and J. B. Weber: Herbicide phytotoxicity as influenced by adsorption. Soil Sci. 104, 151 (1967).

    Article  CAS  Google Scholar 

  • Shainberg, I., and W. D. Kemper: Conductance of adsorbed alkali cations in aqueous and alcoholic bentonite pastes. Soil Sci. Soc. Amer. Proc. 30, 700 (1966).

    CAS  Google Scholar 

  • Sheets, T. J., A. S. Crafts, and H. R. Drever: Influence of soil properties on the phytotoxicities of the s-triazine herbicides. J. Agr. Food Chem. 10, 458 (1962).

    Article  CAS  Google Scholar 

  • Smolin, E. M., and L. Rapoport: s-Triazines and derivatives. New York: Inter-science (1959).

    Google Scholar 

  • Talbert, R. E., and O. H. Fletchall: The adsorption of some s-triazines in soils. Weeds 13, 46 (1965).

    Article  CAS  Google Scholar 

  • Talibudeen, O.: Complex formation between montmorillonoid clays and amino-acids and proteins. Trans. Faraday Soc. 51, 582 (1955).

    Article  CAS  Google Scholar 

  • Upchurch, R. P.: Behavior of herbicides in soil. Residue Reviews 16, 46 (1966).

    CAS  Google Scholar 

  • Van Olphen, H.: Interlayer forces in bentonite. Clays and Clay Minerals, 2d Conf. p. 418 (1954).

    Google Scholar 

  • Ward, T. M., and J. B. Weber: Aqueous solubility of alkylamino-s-triazines as a function of pH and molecular structure. J. Agr. Food Chem. 16, 959 (1968).

    Article  CAS  Google Scholar 

  • Ward, T. M.: Ultraviolet adsorption spectra of alkyamino-s-triazines. Spectrochimica Acta 25A, 1167 (1969).

    Article  Google Scholar 

  • Weber, J. B.: Molecular structure and pH effects on the adsorption of 13.s-triazine compounds on montmorillonite clay. Amer. Mineralog. 51, 1657 (1966).

    CAS  Google Scholar 

  • Weber, J. B.: Spectrophotometrically determined ionization constants of 13 alkylamino-striazines and the relationships of molecular structure and basicity. Spectrochimica Acta 23A, 458 (1967).

    CAS  Google Scholar 

  • Weber, J. B.: Revolution in farm chemicals. Crops and Soils. 21(5), 11 (1969).

    Google Scholar 

  • Weber, J. B., and H. D. Coble: Microbial decomposition of diquat adsorbed on mont- morillonite and kaolinite clays. J. Agr. Food Chem. 16, 475 (1968).

    Article  CAS  Google Scholar 

  • Weber, J. B., R. C. Meek, and S. B. Weed: The effect of CEC on the retention of diquat, and paraquat by three-layer type clay minerals. II. Plant availability of paraquat. Soil Sei. Soc. Amer. Proc. 33, 382 (1969a).

    CAS  Google Scholar 

  • Weber, J. B., P. W. Perry, and K. Ibarakz: Effect of pH on the phytotoxicity of prometryne applied to synthetic soil media. Weed Sci. 16, 134 (1968a).

    CAS  Google Scholar 

  • Weber, J. B., and R. P. Upchurch: The influence of temperature and time on the adsorption of paraquat, diquat, 2,4-D, and prometone by clays, charcoal, and an anion-exchange resin. Soil Sci. Soc. Amer. Proc. 29, 678 (1965).

    CAS  Google Scholar 

  • Weber, J. B., and D. C. Scorn: Availability of a cationic herbicide adsorbed on clay minerals to cucumber seedlings. Science 152, 1400 (1966).

    Article  PubMed  CAS  Google Scholar 

  • Weber, J. B., and S. B. Weed: Adsorption and desorption of diquat, paraquat, and prometone by montmorillonitic and kaolinitic clay minerals. Soil Sci. Soc. Amer. Proc. 32, 584 (1968).

    Google Scholar 

  • Weber, J. B., T. M. Ward, and S. B. Weed: Adsorption and desorption of diquat, paraquat, prometone, and 2,4-D by charcoal and exchange resins. Soil Sci. Soc. Amer. Proc. 32, 197 (1968b).

    CAS  Google Scholar 

  • Weber, J. B., S. B. Weed, and J. A. Best: Displacement of diquat, a cationic herbicide, from clay and its phytotoxicity. J. Agr. Food Chem. 17, 1075 (1969b).

    Article  CAS  Google Scholar 

  • Weber, J. B., and T. M. Ward: Adsorption of s-triazines on soil organic matter. Weed Sci. 17, 417 (1969c).

    CAS  Google Scholar 

  • Weed, S. B., and J. B. Weber: The effect of adsorbent charge on the competitive adsorption of divalent organic cations by layer-silicate minerals. Amer. Mineralog. 53, 478 (1968).

    CAS  Google Scholar 

  • Weiss, A.: Mica-type layer silicates with alkylammonium ions. Clays and Clay Minerals, 10th Conf., p. 191 (1963).

    Google Scholar 

  • Wicklander, L.: Cation and anion exchange phenomena. In F. E. Bear (ed.): Chemistry of the soil, pp. 163–205. New York: Reinhold (1965).

    Google Scholar 

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Authors and Affiliations

  1. Departments of Crop Science and Soil Science, North Carolina State University, Raleigh, N.C., USA

    Jerome B. Weber

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  1. Jerome B. Weber
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  1. Department of Entomology, University of California, Riverside, California, USA

    Francis A. Gunther

  2. Riverside, California, USA

    Jane Davies Gunther

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Weber, J.B. (1970). Mechanisms of adsorption of s-triazines by clay colloids and factors affecting plant availability. In: Gunther, F.A., Gunther, J.D. (eds) Single Pesticide Volume: The Triazine Herbicides. Residue Reviews / Rückstands-Berichte, vol 32. Springer, New York, NY. https://doi.org/10.1007/978-1-4615-8464-3_5

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