Enhancement of the Diffusion of Active Ingredients in Barley Leaf Cuticular Wax by Monodisperse Alcohol Ethoxylates

Journal of Agricultural and Food Chemistry

Volumn 46, Issue 4, 1998, Pages 1593-1602

  Burghardt, Markus ^a   Schreiber, Lukas ^a   Riederer, Markus ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

Alcohol ethoxylate adjuvants; Cuticular wax; Diffusion coefficient; Foliar uptake; Hordeum vulgae

Indexed keywords

HORDEUM; HORDEUM VULGARE SUBSP. VULGARE;

EID: 0001181241     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf970737g     Document Type: Article

References (66)

1. Abraham, M. H.; McGowan, J. C. The Use of Characteristic Volumes to Measure Cavity Terms in Reversed Phase Liquid Chromatography. Chromatographia 1987, 23, 243-246.
2. Albert, A.; Serjeant, E. P. The Determination of Ionization Constants; Wiley: New York, 1962.
3. Baker, E. A. Chemistry and Morphology of Plant Epicuticular Waxes. In The Plant Cuticle; Cutler, D. F., Alvin, K. L., Price, C. E., Eds.; Academic Press: London, 1982; pp 139-165.
4. Bauer, H.; Schönherr, J. Determination of Mobilities of Organic Compounds in Plant Cuticles and Correlation with Molar Volumes. Pestic. Sci. 1992, 35, 1-11.
5. Baur, P. Barriereeigenschaften pflanzlicher Kutikularmem-branen und ihre Beeinflussung durch organische Xenobiotika. Ph.D. Dissertation, Technische Universität München, 1993.
6. Baur, P.; Marzouk, H.; Schönherr, J.; Bauer, H. Mobilities of Organic Compounds in Plant Cuticles as Affected by Structure and Molar Volumes of Chemicals and Plant Species. Planta 1996, 199, 404-412.
7. Baur, P.; Schönherr, J. Die Aufnahme systemischer Wirkstoffe über Blätter: Grundlagen und Optimierung (The uptake of systemic active ingredients by leaves: principles and optimization). Gartenbauwissenschaft 1996, 61, 105-115.
8. Baur, P.; Grayson, B. T.; Schönherr, J. Polydisperse Ethoxylated Fatty Alcohol Surfactants as Accelerators of Cuticular Penetration: 1. Effects of Ethoxy Chain Length and the Size of the Penetrants. Pestic. Sci. 1997, in press.
9. Baur, P.; Schönherr, J. Penetration of an Ethoxylated Fatty Alcohol Surfactant across Leaf Cuticles as Affected by Concentration, Additives and Humidity. Z. Pflanzenkr. Pflanzensch. 1997a, 104, 380-393.
10. Baur, P.; Marzouk, H.; Schönherr, J.; Grayson, B. T. Partition Coefficients of Active Ingredients between Plant Cuticle and Adjuvants As Related to Rates of Foliar Uptake. J. Agric. Food Chem. 1997b, 45, 3659-3665.
11. Bayer, D. E.; Lumb, J. M. Penetration and Translocation of Herbicides. In Pesticide Formulations; Van Valkenburg, W., Ed.; Dekker: New York, 1979; pp 387-439.
12. Bianchi, G. Plant Waxes. In Waxes: Chemistry, Molecular Biology and Functions; Hamilton, R. J., Eds.; The Oily Press: West Ferry, Dundee, Scotland, 1995; pp 175-222.
13. Bukovac, M. J. Herbicide Entry into Plants. In Herbicides; Audus, L. J., Ed.; Academic Press: London, 1976; Vol. 1, pp 335-364.
14. Bukovac, M. J.; Petracek, P. D. Characterizing Pesticide and Surfactant Penetration with Isolated Plant Cuticles. Pestic. Sci. 1993, 37, 179-194.
15. Büscher, K. E. Messung der Dichte, des spezifischen Volumens und des kubischen Ausdehnungskoeffizienten plastischer Massen mit Hilfe des Haake-Konsistometers. Erdoel Kohle 1960, 13, 102-106.
16. Cadogan, D. F.; Howick, C. J. Plasticizers. In Ullmann's Encyclopedia of Industrial Chemistry; Elvers, B., Hawkins, S., Schulz, G., Eds.; VCH Verlag: Weinheim, 1992; Vol. A20, pp 439-458.
17. 14C]-Isoproturon Through Isolated Plant Cuticles. Plant Physiol. Biochem. 1992, 30, 713-721.
18. 14C]Chlorotoluron across Isolated Plant Cuticles. Weed Res. 1994, 34, 445-451.
19. 14C]Chlorotoluron across Isolated Plant Cuticles. Pestic. Sci. 1995, 43, 163-166.
20. Crank, J., Park, G. S., Eds. Diffusion in Polymers; Academic Press: London, 1968.
21. Durner, J.; Shah, J.; Klessig, D. F. Salicylic Acid and Desease Resistance in Plants. Trends Plant Sci. 1997, 2, 266-274.
22. Felder, R. M.; Huvard, G. S. Permeation, Diffusion, and Sorption of Gases and Vapors. In Methods of Experimental Physics; Marton, L., Marton, C., Eds.; Academic Press: London, 1980; Vol. 16, pp 315-377.
23. Gauvrit, C.; Dufour, J. L. Effects of Adjuvants on Herbicidal Action. II. Effects of a Mixture of Adjuvants on Isoproturon Retention and Penetration in Wheat and Ryegrass. Agronomie 1990, 10, 841-846.
24. Holloway, P. J. The Chemical Constitution of Plant Cutins. In The Plant Cuticle; Cutler, D. F., Alvin, K. L., Price, C. E., Eds.; Academic Press: London, 1982; pp 45-85.
25. Holloway, P. J.; Wong, W. W.-C.; Partridge, H. J.; Seaman, D.; Perry, R. B. Effects of Some Nonionic Polyoxyethylene Surfactants on Uptake of Ethirimol and Diclobutrazol from Suspension Formulations Applied to Wheat Leaves. Pestic. Sci. 1992, 34, 109-118.
26. Hull, H. M. Leaf Structure as Related to Absorption of Pesticides and Other Compounds. Residue Rev. 1970, 31, 1-150.
27. Jost, W. Diffusion in Solids, Liquids, Gases; Academic Press: New York, 1960.
28. Kirkwood, R. C. Use and Mode of Action of Adjuvants for Herbicides: A Review of some Current Work. Pestic. Sci. 1993, 38, 93-102.
29. Kirsch, T.; Kaffarnik, F.; Riederer; M.; Schreiber, L. Cuticular Permeability of the Three Tree Species Prunus laurocerasus L., Ginkgo biloba L. and Jugions regia L.: Comparative Investigation of the Transport Properties of Intact Leaves, Isolated Cuticles and Reconstituted Cuticular Waxes. J. Exp. Bot. 1997, 48, 1035-1045.
30. Knoche, M.; Bukovac, M. J. Surfactants Influence Foliar Absorption of Gibberellic Acid by Sour Cherry Leaves. J. Am. Soc. Hortic. Sci. 1992, 117, 80-84.
31. Knoche, M.; Bukovac, M. J. Considerations in the Use of an Infinite-Dose System for Studying Surfactant Effects on Diffusion in Isolated Cuticles. J. Agric. Food Chem. 1994, 42, 1013-1018.
32. Leo, A.; Hansch, C.; Elkins, D. Partition Coefficients and their Uses. Chem. Rev. 1971, 71, 526-616.
33. Merk, S.; Blume, A.; Riederer, M. Phase Behavior and Crystallinity of Plant Cuticular Waxes Studied by Fourier Transform Infrared Spectroscopy. Planta 1998, 204, 44-53.
34. Nassetta, M.; Remedi, V.; de Rossi, R. H. Effect of Surfactants on the Solubility of Herbicides. J. Agric. Food Chem. 1991, 39, 1175-1178.
35. Potts, R. O.; Guy, R. H. Predicting Skin Permeability. Pharm. Res. 1992, 9, 663-669.
36. Reynhardt, E. C.; Riederer, M. Structure and Molecular Dynamics of the Cuticular Wax from Leaves of Citrus aurantium L. J. Phys. D: Appl. Phys. 1991, 24, 478-486.
37. Reynhardt, E. C.; Riederer, M. Structures and Molecular Dynamics of Plant Waxes. 2. Cuticular Waxes from Leaves of Fagus sylvatica L. and Hordeum vulgare L. Eur. Biophys. J. 1994, 23, 59-70.
38. Riederer, M.; Schönherr, J. Effects of Surfactants on Water Permeability of Isolated Cuticles and on the Composition of Cuticular Waxes. Pestic. Sci. 1990, 29, 85-94.
39. Riederer, M.; Schreiber, L. Waxes - the Transport Barriers of Plant Cuticles. In Waxes: Chemistry, Molecular Biology and Functions; Hamilton, R. J., Ed.; Oily Press: West Ferry, Scotland, 1995; pp 130-156.
40. Riederer, M.; Burghardt, M.; Mayer, S.; Obermeier, H.; Schönherr, J. Sorption of Monodisperse Alcohol Ethoxylates and Their Effects on the Mobility of 2,4-D in Isolated Plant Cuticles. J. Agric. Food Chem. 1995, 43, 1067-1075.
41. Rippen, G. Handbuch der Umweltchemikalien; Ecomed-Verlag: Landsberg/Lech, 1992.
42. Rosen, M. J. Surfactants and Interfacial Phenomena; Wiley: New York, 1989.
43. Schick, M. J. Nonionic Surfactants. Physical Chemistry; Dekker: New York, 1987.
44. Schönherr, J. Effects of Monodisperse Alcohol Ethoxylates on Mobility of 2,4-D in Isolated Plant Cuticles. Pestic. Sci. 1993a, 38, 155-164.
45. Schönherr, J. Effects of Alcohols, Glycols and monodisperse Ethoxylated Alcohols on Mobility of 2,4-D in Isolated Plant Cuticles. Pestic. Sci. 1993b, 38, 213-223.
46. Schönherr, J.; Baur, P. Modelling Penetration of Plant Cuticles by Crop Protection Agents and Effects of Adjuvants on their Rates of Penetration. Pestic. Sci. 1994, 42, 185-208.
47. Schönherr, J.; Baur, P. Effects of Temperature, Surfactants and Other Adjuvants on Rates of Uptake of Organic Compounds. In Plant Cuticles. An Integrated Functional Approach; Kerstiens, G., Ed.; BIOS Scientific Publishers: Oxford, U.K., 1996; pp 135-156.
48. 4) on mobilities of selected pesticides in Citrus leaf cuticles. Z. Pflanzenkr. Pflanzensch. 1997, 104, 246-253.
49. Schönherr, J.; Riederer, M.; Schreiber, L.; Bauer, H. Foliar Uptake of Pesticides and its Activation by Adjuvants: Theories and Methods for Optimization. In Pesticide Chemistry; Frehse, H., Ed.; VCH Verlag: Weinheim, 1991; pp 237-253.
50. Schreiber, L. A Mechanistic Approach Towards Surfactant/ Wax Interactions: Effects of Octaethyleneglycolmonododecylether on Sorption and Diffusion of Organic Chemicals in Reconstituted Cuticular Wax of Barley Leaves. Pestic. Sci. 1995, 45, 1-11.
51. Schreiber, L.; Riederer, M. Determination of Diffusion Coefficients of Octadecanoic Acid in Isolated Cuticular Waxes and their Relationship to Cuticular Water Permeabilities. Plant Cell Environ. 1996, 19, 1075-1082.
52. Schreiber, L.; Schönherr, J. Analysis of Foliar Uptake of Pesticides in Barley Leaves: Role of Epicuticular Waxes and Compartmentation. Pestic. Sci. 1992, 36, 213-221.
53. Schreiber, L.; Schönherr, J. Uptake of two Chlorinated Chemicals in Conifer Needles: Reversibility and Compartmental Analysis. New Phytol. 1993a, 123, 547-554.
54. Schreiber, L.; Schönherr, J. Mobilities of Organic Compounds in Reconstituted Cuticular Wax of Barley Leaves: Determination of Diffusion Coefficients. Pestic. Sci. 1993b, 38, 353-361.
55. Schreiber, L.; Bach, S.; Kirsch, T.; Knoll, D.; Schalz, K.; Riederer, M. A Simple Photometric Device Analysing Cuticular Transport Physiology: Surfactant Effect on Permeability of Isolated Cuticular Membranes of Prunus laurocerasus L. J. Exp. Bot. 1995, 46, 1915-1921.
56. Schreiber, L.; Kirsch, T.; Riederer, M. Transport Properties of Cuticular Waxes of Fagus sylvatica L. and Picea abies (L.) Karst.: Estimation of Size Selectivity and Tortuosity from Diffusion Coefficients of Aliphatic Molecules. Planta 1996a, 198, 104-109.
57. Schreiber, L.; Kirsch, T.; Riederer, M. Diffusion through Cuticles: Principles and Models. In Plant Cuticles. An Integrated Functional Approach; Kerstiens, G., Ed.; BIOS Scientific Publishers: Oxford, U.K., 1996b; pp 109-120.
58. Schreiber, L.; Riederer, M.; Schorn, K. Mobilities of Organic Compounds in Reconstituted Cuticular Wax of Barley Leaves: Effects of Monodisperse Alcohol Ethoxylates on Diffusion of Pentachlorophenol and Tetracosanoic Acid. Pestic. Sci. 1996c, 48, 117-124.
59. 2H NMR Study of Cuticular Wax Isolated from Hordeum vulgare L. Leaves: Identification of Amorphous and Crystalline Wax Phases. Eur. Biophys. J. 1997, 16, 371-380.
60. Shafer, W. E.; Bukovac, M. J. Studies on Octylphenoxy Surfactants. 7. Effects of Triton X-100 on Sorption of 2-(1-Naphthylacetic) Acid by Tomato Fruit Cuticles. J. Agric. Food Chem. 1989, 37, 486-492.
61. Steurbaut, W. Adjuvants for Use with Foliar Fungicides. Pestic. Sci. 1993, 38, 85-91.
62. Stevens, P. J. G.; Kimberley, M. O.; Murphy, D. S.; Policello, G. A. Adhesion of Spray Droplets to Foliage: The Role of Dynamic Surface Tension and Advantages of Organosilicone Surfactants. Pestic. Sci. 1993, 38, 237-245.
63. Stock, D.; Edgerton, B. M.; Gaskin, R. E.; Holloway, P. J. Surfactant-Enhanced Foliar Uptake of Some Organic Compounds: Interactions with Two Model Polyoxyethylene Aliphatic Alcohols. Pestic. Sci. 1992, 34, 233-242.
64. Stock, D.; Holloway, P. J. Possible Mechanisms for Surfactant-Induced Foliar Uptake of Agrochemicals. Pestic. Sci. 1993, 38, 165-177.
65. Tan, S.; Crabtree, G. D. Effects of Nonionic Surfactants on Cuticular Sorption and Penetration of 2,4-Dichlorophenoxy Acetic Acid. Pestic. Sci. 1992, 35, 299-303.
66. Vieth, W. R. Diffusion in and through Polymers; Carl Hanser Verlag: München, 1991.