Abstract
Irradiation of carboxin (1) with a 500W UV lamp (filter Pyrex) in CH3CN leads to the products 3, 5–8, 12–14 depending upon the reaction conditions. All photo-products were isolated and characterized. Photooxidation occurred even if unsensitized, while photoalteration was very slow in the absence of oxygen. The main oxygenated-products 3 and 13 were also recovered under biomimetic conditions by exposure of an aqueous solution of 1 to sunlight.
References
Snel M, von Schmeling B, Edgington LV (1970): Fungitoxicity and Structure-Activity Relationship of Some Oxathiin and Thiazole Derivatives. Phytopathology 60, 1164–1168
Wolkoff AW, Onuska FI, Comba ME, Larose RH (1975): Determination of 5,6-Dihydro-2-methyl-l,4-oxathiin-3-carboxanilide (Vitavax) and Two of Its Photoproducts by High Speed Liquid Chromatography. Analytical Chemistry 47, 754–756
See for example: Tsao R, Eto M (1994): Effect of Some Natural Photosensitizers on Photolysis of Some Pesticides. In: Helz GR, Zepp RG, Crosby DG (Eds): Aquatic and Surface Photochemistry, Lewis Publishers, Boca Raton (Fl), pp 163–171
Foote CS, Valentine JS, Greenberg A, Liebman JF (1995): Active Oxygen in Chemistry, Chapman & Hall, London, Vol 2
Iesce MR, Cermola F, De Lorenzo F, Graziano ML, Giordano F, Palumbo G (2000): Unexpected Products via Singlet Oxygen Oxygenation of Functionalized 5,6-Dihydro-l,4-oxathiins. Org Lett 2, 1205–1207
Kavarnos GJ, Turro NJ (1986): Photosensitization by Reversible Electron Transfer: Theories, Experimental Evidence, and Examples. Chem Rev 86, 401–449
Ando W, Takata T (1985): Photooxidation of Sulfur Compounds. In: Frimer AA (Ed): Singlet O2, CRC Press, Boca Raton (Fl), Vol III, 1–117
Coyle JD (1986): Introduction to Organic Photochemistry, Wiley, New York, p 101
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Iesce, M.R., Cermola, F., De Lorenzo, F. et al. Photochemical behaviour of the systemic fungicide carboxin. Environ Sci & Pollut Res 9, 107–109 (2002). https://doi.org/10.1007/BF02987455
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF02987455