Photodegradation of Dialkyl 1,3-Dithiolan-2-ylidenemalonates and Some Other Pesticides on Solid Particles

Abstract

On irradiation with UV light the fungicide isoprothiolane (diisopropyl 1,3-dithiolan-2-ylidenemalonate) decomposed rapidly on the silica gel surface. The degradation pathways involved dithiolane ring cleavage, ester hydrolysis, decarboxylation, heterocycles formation such as dithietane and trithiolane, and sulfur liberation. The photoproducts confirmed were oxalic acid, dithiolanylidenemalonic acid, dithiolanylideneacetic acid, 2,4-bis[bis(isopropoxycar-bonyl)methylene]-1, 3-dithietane, 3, 5-bis[bis(isopropoxy-carbonyl)methylene]-1,2,4-trithiolane and sulfur. The methyl and ethyl homologs of isoprothiolane similarly gave the corresponding photoproducts. The surface area where isoprothiolane was placed appeared to be related closely with the photolysis rate. Isoprothiolane decomposed much more rapidly on sand than on a glass plate. This surface effect was greatly depressed under nitrogen atmosphere. Similar phenomena were observed with some other pesticides, with particularly those containing sulfur atoms in the molecule.