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Photochemical behaviour of phenylurea herbicides

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Abstract

The photochemical behaviour of phenylurea herbicides in aqueous solution is highly dependent on the nature and position of substituents on the ring. Most of these herbicides are methylated on the urea moiety, the other substituents are usually halogens or methoxy groups. The main reaction involving the aromatic ring of unhalogenated phenylureas excited at wavelengths shorter than 300 nm is an intramolecular rearrangement, similar to photo-Fries rearrangement, whereas with halogenated derivatives, photohydrolysis is the main transformation pathway. In the particular case of para-halogenated phenylureas, the intermediate formation of a carbene is observed. When the urea moiety is substituted with a methoxyl group, demeth-oxylation is a competitive reaction. N-Demethylation or oxidation of methyl groups is also observed, but with a lower yield. Photooxidation of phenylureas can also be induced by photocatalysis, iron salts or humic substances. In the absence of water, the main route for phototransformation of diuron is the oxidation or elimination of methyl groups. It is entirely possible that a photochemical intermediate could turn out to be more toxic than the initial herbicide.

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Authors and Affiliations

  1. Laboratoire des Sciences et Technologies de l’Environnement, Université Mentouri, Route de Aïn El Bey, 25000, Constantine, Algérie

    Amina Amine-Khodja & Abdelaziz Boulkamh

  2. Laboratoire de Photochimie Moléculaire et Macromoléculaire, UMR Université Blaise Pascal/CNRS 6505, F-63177, Aubière cedex, France

    Pierre Boule

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  1. Amina Amine-Khodja
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  2. Abdelaziz Boulkamh
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  3. Pierre Boule
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Correspondence to Pierre Boule.

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† Dedicated to Professor Jean Kossanyi in recognition of his outstanding contribution to the development of photochemistry and for his devoted service to both the EPA and the French Group of Photochemistry.

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Amine-Khodja, A., Boulkamh, A. & Boule, P. Photochemical behaviour of phenylurea herbicides. Photochem Photobiol Sci 3, 145–156 (2004). https://doi.org/10.1039/b307968f

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