title: Photochemical transformation of atrazine and formation of photointermediates under conditions relevant to sunlit surface waters: laboratory measures and modelling.
abstract: By combination of laboratory experiments and modelling, we show here that the main photochemical pathways leading to the transformation of atrazine (ATZ, 2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine) in surface waters would be direct photolysis, reaction with ·OH and with the triplet states of chromophoric dissolved organic matter ((3)CDOM*). Reaction with (3)CDOM* would be favoured by elevated water depth and dissolved organic carbon content, while opposite conditions would favour direct photolysis and OH reaction. Desethylatrazine (DEA, 4-amino-2-chloro-6-isopropylamino-1,3,5-triazine) was the main detected intermediate of ATZ phototransformation. Its formation yield from ATZ (ratio of DEA formation to ATZ transformation rate) would be 0.93 ± 0.14 for ·OH, 0.55 ± 0.05 for (3)CDOM*, and 0.20 ± 0.02 for direct photolysis. Direct photolysis and ·OH reaction also yielded 4-amino-2-hydroxy-6-isopropylamino-1,3,5-triazine (DEAOH) and 6-amino-2-chloro-4-ethylamino-1,3,5-triazine (DIA). Reaction with excited triplet states also produced 2-hydroxy-4,6-diamino-1,3,5-triazine (AN) and 2-chloro-4,6-diamino-1,3,5-triazine (CAAT). Therefore, if biological processes can be neglected and if the low formation yields do not prevent detection, DEAOH and DIA could be used as markers of ATZ direct photolysis and ·OH reaction, while AN and CAAT could be markers of ATZ reaction with (3)CDOM*. Model predictions concerning ATZ phototransformation were compared with available field data from the literature. When sufficiently detailed field information was provided, good agreement was found with the model.
authors: Università degli Studi di Torino, Dipartimento di Chimica, Via P. Giuria 5, 10125 Torino, Italy(1); LAV s.r.l., Strada Carignano 58/14, 10024 Moncalieri (TO), Italy(2).
authors: Giulia
authors: G
authors: Marchetti
authors: Marco
authors: M
authors: Minella
authors: Valter
authors: V
authors: Maurino
authors: Claudio
authors: C
authors: Minero
authors: Davide
authors: D
authors: Vione
mesh_terms: D001280:Atrazine / Q000737:chemistry*; D006540:Herbicides / Q000737:chemistry*; D008962:Models, Theoretical; D010777:Photochemistry; D014874:Water Pollutants, Chemical / Q000737:chemistry*
chemical_list: D006540:Herbicides; D014874:Water Pollutants, Chemical; D001280:Atrazine
keywords: Atrazine; Environmental modelling; Indirect photolysis; Pesticides; Photosensitisers; Surface-water photochemistry