Photochemical behavior of alloxydim herbicide in environmental waters. Structural elucidation and toxicity of degradation products

Sandín‐España, Pilar; Sevilla-Morán, Beatriz; Calvo, L.; Mateo-Miranda, Miguelina M.; Alonso‐Prados, José Luis

doi:10.1016/j.microc.2012.07.003

Cited by 38 publications

(34 citation statements)

References 17 publications

(23 reference statements)

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“…Therefore, it is expected that one of the most important reactions of CHD herbicides is the cleavage of the N-O bond to yield two possible dealkoxylated compounds, imine and/or amine (Table 3). Thus, photodegradation of alloxydim in aqueous solution was investigated under simulated and natural solar light and the main photoproduct obtained was the imine [45,73]. Both studies revealed that the amount of alloxydim imine formed can be influenced by the composition of aqueous solution and the intensity of radiation source [45].…”

Section: Transformation Productsmentioning

confidence: 99%

Degradation of Cyclohexanedione Oxime Herbicides

Sevilla-Morán¹,

López-Goti²,

Alonso‐Prados³

et al. 2013

Herbicides - Advances in Research

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Section: Transformation Productsmentioning

confidence: 99%

Degradation of Cyclohexanedione Oxime Herbicides

Sevilla-Morán¹,

López-Goti²,

Alonso‐Prados³

et al. 2013

Herbicides - Advances in Research

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“…In addition, Alloxydim was investigated with a standard microtest procedure based on the decrease of light emission by the marine bacterium Vibrio fischeri. The results indicated that the toxicity of the photoproducts was higher than the toxicity of the parent compound (Sandín-España et al 2013).…”

Section: Discussionmentioning

confidence: 95%

Micronucleus assay in human lymphocytes after exposure to alloxydim sodium herbicide in vitro

et al. 2014

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This study evaluates the cytotoxic and genotoxic potential of alloxydim sodium using micronucleus (MN) assay, in human peripheral lymphocytes. MN assay was used to investigate the genotoxic effects of alloxydim sodium in human peripheral lymphocytes treated with 250, 500, 750, 1,000 lg/ml concentrations of alloxydim sodium for 24 and 48 h. Solvent, negative and positive controls were also used in the experiments in parallel. The obtained results were evaluated in statistical analyses by using Dunnett-t test (two sided) and p \ 0.05 was accepted as significant. Alloxydim sodium significantly increased the MN formation compared with the negative control, at both 750 and 1,000 lg/ml concentrations and treatment periods. We also evaluated the nuclear division index (NDI) for cytotoxicity of this pesticide in the experiment, and finally observed a significant decrease of the NDI values at all concentrations of alloxydim sodium and at both treatment periods.

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“…4) In the case of triclosan rearranging at 300 nm to the diphenyl derivative, a different biradical mechanism was proposed via one-electron reduction, followed by the release of Cl − . 75) Cyclohexene oxime herbicides such as alloxydim 119) generally undergo photo-induced N-O cleavage to form the corresponding imines. The succeeding hydrolysis produced the ketone derivative in the case of tralkoxydim.…”

Section: Ethersmentioning

confidence: 99%

“…4) The photoisomerization from anti (E) to syn (Z) of the oxime ether clethodim 186) and fenpyroximate 4,121) proceeded rapidly, while it was of minor importance for alloxydim 119) and sethoxydim 120) due to a more favorable N-O bond cleavage. Incidentally, pyrethroids that have a cyclopropyl moiety are known to undergo cis-trans isomerization via the homolytic cleavage of the C 1 -C 3 bond, followed by the recombination of the resulting biradical.…”

Section: Rearrangement 331 Isomerization 3311 Geometrical Isommentioning

confidence: 99%

Direct photolysis mechanism of pesticides in water

Katagi

2018

Journal of Pesticide Science

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Photodegradation is one of the most important abiotic transformations for pesticides in the aquatic environment, and the high energy of sunlight causes characteristic reactions such as bond scission, cyclization, and rearrangement, which are scarcely observed in hydrolysis and microbial degradation. This review deals with direct photolysis via excitation of a pesticide by absorbing natural or artificial sunlight in order to know its basic photochemistry, and indirect photolysis meaning either sensitization by dissolved organic matters or oxidation by reactive oxygen species is basically excluded. Several experimental approaches including spectroscopic techniques together with theoretical calculations are first discussed from the viewpoint of the reaction mechanisms in direct photolysis. Then, the typical photoreactions of pesticides are summarized by chemical classes and/or functional groups and discussed as far as possible in relation to their mechanisms.

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Photochemical behavior of alloxydim herbicide in environmental waters. Structural elucidation and toxicity of degradation products

Cited by 38 publications

References 17 publications

Degradation of Cyclohexanedione Oxime Herbicides

Degradation of Cyclohexanedione Oxime Herbicides

Micronucleus assay in human lymphocytes after exposure to alloxydim sodium herbicide in vitro

Direct photolysis mechanism of pesticides in water

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