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Photochemistry and Photoinduced Toxicity of Acifluorfen, a Diphenyl-Ether Herbicide

^a Dipartimento di Produzione Vegetale, Università della Basilicata, Via N. Sauro 85, I 85100 Potenza, Italy
^b Dipartimento di Chimica, Università della Basilicata, Via N. Sauro 85, I 85100 Potenza, Italy
^c L.A.C.E., Université Claude Bernard Lyon I, 43 Bd du 11 novembre 1918, F 69622 Villeurbanne Cedex, France
^d GSF-National Research Centre for Environment and Health, Institute of Ecological Chemistry, Ingolstädter Landstrasse 1, D 85764 Neuherberg-München, Germany

View larger version (15K): [in a new window]   Fig. 1. Illustration of Scheme 1, showing the mechanism of acifluorfen photodegradation (20% transformed).

View larger version (18K): [in a new window]   Fig. 2. Ultraviolet spectra of acifluorfen (0.1 mM) in different solvents.

View larger version (12K): [in a new window]   Fig. 3. Fluorescence spectrum of acifluorfen (0.1 mM in acetonitrile vs. diphenyl-anthracene [DPA] as the actinometer); exc = 288 nm, em = 300 nm.

View larger version (12K): [in a new window]   Fig. 4. Phosphorescence emission of acifluorfen (0.1 mM in the mixture of ethylether, 2-methylbutane, and ethanol [5:5:2] [EPA] vs. acetophenone as the actinometer); exc = 290 nm, em = 410 nm.

View larger version (21K): [in a new window]   Fig. 5. Degradation curves of acifluorfen (0.1 mM) in different solvents (xenon arc [Suntest irradiation]).

View larger version (18K): [in a new window]   Fig. 6. Degradation curves of acifluorfen (0.1 mM) in different solvents (UV mercury arc).

View larger version (8K): [in a new window]   Fig. 7. Further by-products found after 36 h of irradiation (98% acifluorfen transformed).

View larger version (17K): [in a new window]   Fig. 8. Illustration of Scheme 2, showing the mechanism of cleavage of the ether linkage of acifluorfen followed by the rearrangement of the molecule to give the product 5-trifluoromethyl-5'-nitrodibenzofuran.