Hostname: page-component-848d4c4894-m9kch Total loading time: 0 Render date: 2024-05-02T11:24:36.327Z Has data issue: false hasContentIssue false
  • English
  • Français

Photostabilization of a Nitromethylene Heterocycle Insecticide on the Surface of Montmorillonite

Published online by Cambridge University Press:  02 April 2024

L. Margulies ,
H. Rozen  and
E. Cohen
L. Margulies
Affiliation:
Seagram Centre for Soil and Water Sciences, Faculty of Agriculture, The Hebrew University, Rehovot 76-100, Israel
H. Rozen
Affiliation:
Seagram Centre for Soil and Water Sciences, Faculty of Agriculture, The Hebrew University, Rehovot 76-100, Israel
E. Cohen
Affiliation:
Department of Entomology, Faculty of Agriculture, The Hebrew University, Rehovot 76-100, Israel
Get access Rights & Permissions [Opens in a new window]

Abstract

The photochemical stability of the insecticidal compound tetrahydro-2-(nitromethylene)-2H-1,3-thiazine (NMH) adsorbed on montmorillonite (Mont), in the presence or in the absence of a second organic chromophore was studied. Two different organic dyes were investigated as possible stabilizers of NMH: the divalent cation methyl green (MG) and the monovalent cation thioflavin T (TFT). Samples of free NMH and of the adsorption complexes Mont-NMH, Mont-MG-NMH, and Mont-TFT-NMH were exposed to direct sunlight, and the residual insecticidal activity was estimated. Some photostabilization of the pesticide adsorbed to the clay was observed. The highest degree of photoprotection was achieved in samples containing 0.5 mmole of TFT and 0.2 mmole of NMH/g clay. Increasing the load of TFT to 0.8 mmole/g clay resulted in a complete loss of photostabilization. The interactions of the organic molecules at the clay surface were studied by UV-VIS absorption and Fourier-transform infrared spectroscopy. For the Mont-NMH and Mont-MG-NMH complexes, the observed photostabilization is probably due to clay-NMH interactions. In the Mont-TFT-NMH complex specific interactions between the cationic dye and the pesticide molecules probably occurred as well.

Keywords

AdsorptionClay-organic complexInfrared spectroscopyMontmorilloniteNitromethylene heterocyclePesticidePhotostabilization
Type
Research Article
Information
Clays and Clay Minerals , Volume 36 , Issue 2 , April 1988 , pp. 159 - 164
Copyright
Copyright © 1988, The Clay Minerals Society

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

Anvir, D., Grauer, Z., Huppert, D., Rojanksi, D. and Yariv, S., 1986 Electronic energy transfer on clay surfaces. Rhodamine 6G to cationic dye acceptors Nouv. J. Chem. 10 153 – 157.Google Scholar
DellaGuardia, R. A. and Thomas, J. K., 1983 Photoprocesses on colloidal clay systems. Tris(2,2′-bipyridine)-ruthenium(Ii) bound to colloidal kaolin and montmorillonite J. Phys. Chem. 87 990 – 998.CrossRefGoogle Scholar
DellaGuardia, R. A. and Thomas, J. K., 1983 Photoprocesses on colloidal clay systems. 2. Quenching studies and the eifect of surfactants on the luminescent properties of pyrene and pyrene derivatives adsorbed on clay colloids J. Phys. Chem. 87 3550 – 3557.CrossRefGoogle Scholar
DellaGuardia, R. A. and Thomas, J. K., 1984 Photoprocesses on colloidal clay systems. 3. Interaction of dodecanol and its micelles with colloidal montmorillonite J. Phys. Chem. 88 964 – 970.CrossRefGoogle Scholar
Kleier, D., Holden, I., Casida, J. E. and Ruzo, L. O., 1985 Novel photoreactions of an insecticidal nitromethylene het-erocycle J. Agric. Food Chem. 33 998 – 1000.CrossRefGoogle Scholar
Krenske, D., Abdo, S., Van Damme, H., Cruz, M. and Fripiat, J. J., 1980 Photochemical and photocatalytic properties of adsorbed organometallic compounds. Luminescence quenching of tris(2,2’-bipyridine)ruthenium(II) and chromium(III) in clay membranes J. Phys. Chem. 84 2447 – 2457.CrossRefGoogle Scholar
Margulies, L., Cohen, E. and Rozen, H., 1987 Photostabilization of bioresmethrin by organic cations on a clay surface Pest. Sci. 18 79 – 87.CrossRefGoogle Scholar
Margulies, L. and Rozen, H., 1986 Adsorption of methyl green on montmorillonite J. Molec. Structure 141 219 – 226.CrossRefGoogle Scholar
Margulies, L., Rozen, H. and Cohen, E., 1985 Energy transfer at the surface of clays and protection of pesticides from photodegradation Nature 315 658 – 659.CrossRefGoogle Scholar
Mortland, M. M., 1970 Clay-organic complexes and interactions Adv. Agron. 22 75 – 117.CrossRefGoogle Scholar
Nakamura, T. and Thomas, J. K., 1985 Photochemistry of materials adsorbed on clay systems. Effect of the nature of the adsorption on the kinetic description of the reactions Langmuir 1 568 – 573.CrossRefGoogle Scholar
Nakamura, T. and Thomas, J. K., 1986 The interaction of alkylammonium salts with synthetic clays. A fluorescence and laser excitation study J. Phys. Chem. 90 641 – 644.CrossRefGoogle Scholar
Nakanish, K. and Soloman, P. H., 1977 Infrared Absorption Spectroscopy California Holden Day, Oakland.Google Scholar
Plimmer, J. R. and Tahori, A. S., 1972 Photochemistry of pesticides: A discussion of the influence of some environmental factors Fate ofPesticides in Environment London Gordon and Breach 47 – 76.Google Scholar
Pouchen, C. J., 1981 The Aldrich Library of Infrared Spectra Wisconsin Aldrich Chemical Company, Inc..Google Scholar
Schoonheydt, R. A., De Pauw, P., Vliers, D. and De Schrijver, F. C., 1984 Luminescence of tris(2,2′-bipyridine)-ruthenium(II) in aqueous clay mineral suspensions J. Phys. Chem. 88 5113 – 5118.CrossRefGoogle Scholar
Soloway, S. B., Henry, A. C., Kollmeyer, W. D., Padgett, W. M., Powell, J. E., Roman, S. A., Tieman, C. H., Corey, R. A., Home, C. A., Shankland, D. L., Hollingworth, R. M. and Smyth, T. Jr., 1978 Nitromethylene heterocycles as insecticides Pesticides and Venom Neurotoxicity New York Plenum 153 – 158.CrossRefGoogle Scholar
Theng, B. K. G., 1974 The Chemistry of Clay-Organic Reactions New York Wiley.Google Scholar