UV-visible degradation of boscalid - structural characterization of photoproducts and potential toxicity using<i>in silico</i>tests

Lassalle, Yannick; Kinani, Aziz; Rifai, Ahmad; Souissi, Yasmine; Clavaguéra, Carine; Bourcier, Sophie; Jaber, Farouk; Bouchonnet, Stéphane

doi:10.1002/rcm.6880

Cited by 16 publications

(19 citation statements)

References 25 publications

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“…Nevertheless, some of the described photoproducts can be found in environmental samples, e.g. boscalid photoproducts were found on grape leaves treated under field conditions . The present work focuses on the phototransformation of fludioxonil in aqueous solution.…”

Section: Introductionmentioning

confidence: 99%

“…boscalid photoproducts were found on grape leaves treated under field conditions. [17] The present work focuses on the phototransformation of fludioxonil in aqueous solution. Fludioxonil was introduced by Ciba-Geigy in 1990 to be primarily used as a foliar fungicide in order to control Botrytis cinerea, Monilinia, Sclerotinia, Rhizoctonia and Alternaria.…”

Section: Introductionmentioning

confidence: 99%

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Structural elucidation and estimation of the acute toxicity of the major UV–visible photoproduct of fludioxonil – detection in both skin and flesh samples of grape

et al. 2015

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Ultraviolet (UV)-visible irradiation of fludioxonil was investigated with two photoreactors using either a mercury or xenon vapor lamp. In both cases, it led to the formation of only one photoproduct in significant amount: 2-(2,2-difluorobenzo[d][1,3]dioxol-4-yl)-2-(nitrosomethylene)-4-oxobutanenitrile, which has been characterized using Liquid Chromatography - High Resolution - Tandem Mass Spectrometry (LC-HR-MS/MS) coupling. A photolysis pathway has been proposed to rationalize its formation in degassed water. In vitro bioassays on Vibrio fischeri bacteria showed that UV-vis irradiation of an aqueous solution of fludioxonil significantly increases its toxicity. Because no other by-product was detected in significant amount, the photoproduct mentioned above may be considered mainly responsible for this increase in toxicity. Grape berries treated with a 50 ppm aqueous solution of fludioxonil were submitted to UV-visible irradiation under laboratory conditions. The fungicide and photoproduct were detected in both skin and flesh of berries, even after they have been rinsed with water. The ability of the photoproduct to pass through the fruit skin is comparable with that of fludioxonil. These results are of concern for consumers because they mean that water tap rinsing does not lead to efficient removing of both compounds.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Structural elucidation and estimation of the acute toxicity of the major UV–visible photoproduct of fludioxonil – detection in both skin and flesh samples of grape

et al. 2015

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“…This corresponded to ~88% and up to 100% degradation on glass and apple skin, respectively. Lassalle et al (2014) have previously observed that UV irradiation effectively degrades boscalid residues using a high-pressure mercury lamp irradiating 120 mL quartz tubes in a sonicator at 25 ± 3□C. While the UV dose to samples was not reported, 150 min of exposure of a 5 mg/L aqueous solution of boscalid to a lamp with a radiation flux of 6200 lumens (wavelength 200 to 650 nm) resulted in a 90% decrease in residues.…”

Section: Resultsmentioning

confidence: 99%

“…Using these wash techniques can increase the risk of microbial contamination (CDC, 1989; DiCaprio et al, 2015; Franz et al, 2008; Gombas, 2017). A potential alternative is the use of advanced oxidative processes (AOPs), for example the combinations of multiple treatments such as UV light, hydrogen peroxide, ozone, titanium dioxide and others that are capable of generating hydroxyl or other highly reactive radicals that can degrade pesticide residues (Junges et al, 2013; Lassalle et al, 2014; 2015; Manassero et al, 2010). AOP has been a common technique to degrade pollutants in wastewater for decades and has recently seen some application in the treatment of food commodities for the same purpose.…”

Section: Introductionmentioning

confidence: 99%

Degradation ofboscalid, pyraclostrobin, fenbuconazole, andglyphosateresidues by an advanced oxidative process utilizing ultraviolet light and hydrogen peroxide

Skanes

Ho²,

Warriner³

et al. 2020

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Recently an advanced oxidative process (AOP) combining H2O2 and UV-C light was observed to be effective at controlling Listeria monocytogens (Murray et al., 2018) and Escherichia coli O157:H7 and degrading chlorpyrifos residues on the surface of apples (Ho et al., 2020). Little is known about the application of AOP for the degradation of other pesticide residues. This study examined degradation of boscalid, pyraclostrobin, fenbuconazole and glyphosate by 3% (w/v) H2O2, UV-C (254 nm) irradiation and their combination on apple skin and glass. The extent of degradation was not significantly different between the AOP and optimal individual treatment. However, treatment susceptibility was different with glyphosate most effectively degraded by H2O2 exposure (up to 98% on apple, 3% (w/v) H2O2 at 30□C for 15 min) while boscalid, pyraclostrobin and fenbuconazole were more effectively degraded by UV-C (up to 88%, 100% and 70% degradation after ~11,000 mJ/cm2). Suggestions for possible causes of degradation are proposed.

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“…The first strategy consisted in establishing a list of boscalid metabolites previously identified in the literature in different media or organisms such as rats (Grosshans and Knoell, 2001) or soil (US EPA, 2003). We also included transformation products from electrochemical, photolytic or photocatalytic reactions (Lohmann et al, 2009;Lagunas-Allu e et al, 2010;Lassalle et al, 2014). The exact mass of each potential metabolite was calculated as well as several adducts, namely [MþH] þ , [MþNa] þ and [MþNH 4 ] þ .…”

Section: Analytical Strategy To Detect and Identify The Metabolitesmentioning

confidence: 99%

Detection and quantification of boscalid and its metabolites in honeybees

et al. 2016

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Boscalid is a new-generation fungicide that has been detected in several bee matrices. The objective of this work was to characterize boscalid metabolites in honeybees based on in vivo experimentation, and next to verify the presence of theses metabolites into honeybees from colonies presenting troubles. A methodology based on complementary mass spectrometric tools, namely ultra-high performance liquid chromatography coupled to high-resolution mass spectrometry (UHPLC-QToF) or triple quadrupole mass spectrometry (UHPLC-QqQ) was implemented. Honeybees were sprayed with boscalid, at field rate (to induce the metabolization process) and the parent compound with its generated metabolites were then extracted using modified EU-QuEChERS method. The mass characteristics including exact mass, isotopic profile and mass fragments allowed assuming the structure of several metabolites. Some of them were unambiguously identified by comparison with synthesized analytical standards. The metabolites were resulted from hydroxylation and dechlorination of the parent compound as well as the substitution of a chlorine atom with an hydroxyl group. The metabolites were then quantified in bee samples collected from various beehives located in France. Boscalid and three of its metabolites were present in some samples at a level ranged between 0.2 and 36.3 ng/g.

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UV-visible degradation of boscalid - structural characterization of photoproducts and potential toxicity usingin silicotests

Cited by 16 publications

References 25 publications

Structural elucidation and estimation of the acute toxicity of the major UV–visible photoproduct of fludioxonil – detection in both skin and flesh samples of grape

Structural elucidation and estimation of the acute toxicity of the major UV–visible photoproduct of fludioxonil – detection in both skin and flesh samples of grape

Degradation ofboscalid, pyraclostrobin, fenbuconazole, andglyphosateresidues by an advanced oxidative process utilizing ultraviolet light and hydrogen peroxide

Detection and quantification of boscalid and its metabolites in honeybees

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