Photolysis of the herbicide sulcotrione: formation of a major photoproduct and its toxicity evaluation

Halle, Alexandra ter; Wiszniowski, Jarosław; Hitmi, Adnane; Ledoigt, Gérand; Bonnemoy, Frédérique; Bonnet, Jean‐Louis; Bohatier, Jacques; Richard, Claire

doi:10.1002/ps.1637

Cited by 21 publications

(17 citation statements)

References 15 publications

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“…Although SUL degradation products had no herbicide activity, they present toxicity towards unicellular organisms different of sulcotrione toxicity (Ter Halle et al 2009; Wiszniowski et al 2009). According to Goujon et al (2014), SUL possesses genotoxic properties against Allium cepa L. The detailed physicochemical parameters of all above-mentioned herbicides and their degradation products are placed in Table 1.…”

Section: Introductionmentioning

confidence: 99%

Atrazine, triketone herbicides, and their degradation products in sediment, soil and surface water samples in Poland

Barchańska

Sajdak

Szczypka

et al. 2016

Environ Sci Pollut Res

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The aim of this study was to monitor the sediment, soil and surface water contamination with selected popular triketone herbicides (mesotrione (MES) and sulcotrione(SUL)), atrazine (ATR) classified as a possible carcinogen and endocrine disrupting chemical, as well as their degradation products, in Silesia (Poland). Seventeen sediment samples, 24 soil samples, and 64 surface water samples collected in 2014 were studied. After solid-liquid extraction (SLE) and solid phase extraction (SPE), analytes were determined by high-performance liquid chromatography (HPLC) with diode array detection (DAD). Ten years after the withdrawal from the use, ATR was not detected in any of the collected samples; however, its degradation products are still present in 41 % of sediment, 71 % of soil, and 8 % of surface water samples. SUL was determined in 85 % of soil samples; its degradation product (2-chloro-4-(methylosulfonyl) benzoic acid (CMBA)) was present in 43 % of soil samples. In 17 % of sediment samples, CMBA was detected. Triketones were detected occasionally in surface water samples. The chemometric analysis (clustering analysis (CA), single-factor analysis of variance (ANOVA), N-Way ANOVA) was applied to find relations between selected soil and sediment parameters and herbicides concentration. In neither of the studied cases a statistically significant relationship between the concentrations of examined herbicides, their degradation products and soil parameters (organic carbon (OC), pH) was observed.Electronic supplementary materialThe online version of this article (doi:10.1007/s11356-016-7798-3) contains supplementary material, which is available to authorized users.

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Section: Introductionmentioning

confidence: 99%

Atrazine, triketone herbicides, and their degradation products in sediment, soil and surface water samples in Poland

Barchańska

Sajdak

Szczypka

et al. 2016

Environ Sci Pollut Res

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“…It was shown that photolytic degradation of triketone herbicides substituted by a Cl atom, such as sulcotrione and tembotrione, mainly resulted in efficient formation of a xanthenic derivative by intramolecular photocyclization in acidic form. , Irradiation time and rising photoproduct levels clearly increased the toxicity of the mixture toward tested organisms (V. fischeri and A. cepa ).…”

Section: Results and Discussionmentioning

confidence: 99%

Transformation of the Herbicide Sulcotrione into a Root Growth Enhancer Compound by Sequential Photolysis and Hydrolysis

Goujon

Maruel

Richard

et al. 2016

J. Agric. Food Chem.

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Xanthene-1,9-dione-3,4-dihydro-6-methylsulfonyl (1), the main product of sulcotrione phototransformation on plant leaves, was slowly hydrolyzed into 2-hydroxy-4-methylsulfonylbenzoic acid (2) and 1,3-cyclohexanedione (3) in aqueous solution. Interestingly, the rate of hydrolysis was significantly enhanced in the presence of roots of monocotyledonous plants, while the same treatment showed adverse effects on broadleaf weeds. Root growth enhancement varied according to the plant species and concentrations of compound 2, as shown with Zea mays roots. Compound 2 is a derivative of salicylic acid that is known to be a plant signaling messenger. Compound 2 was, therefore, able to mimic some known effects of this phytohormone. This work showed that a pesticide like sulcotrione was transformed into a compound exhibiting a positive impact on plant growth. This study exemplified a rarely reported situation where chemical and biological chain reactions transformed a xenobiotic into a compound exhibiting potential beneficial effects.

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“…80 The cyclization photoproduct of sulcotrione is more toxic than the parent compound. 85 The ability of river water (2.9 mg C per L, 0 mg NO 3 À per L) to quench the photolysis of the herbicide was attributed to light screening. 80 In the same study, the ability of seawater (1.1 mg C per L, 0.02 mg NO 3 À per L) to accelerate sulcotrione photolysis was attributed to nitrate photolysis.…”

Section: Azole Fungicidesmentioning

confidence: 99%

The role of indirect photochemical degradation in the environmental fate of pesticides: a review

Remucal

2014

Environ. Sci.: Processes Impacts

190

141

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Photochemical degradation contributes to the environmental fate of many pesticides in surface waters. A better understanding of the role of direct and indirect photochemical degradation of pesticides is necessary in order to predict their environmental fate and persistence. This review includes all major pesticide classes and focuses on the importance of dissolved organic matter (DOM) as a sensitizer in indirect photodegradation within aquatic systems. Photochemical studies conducted under environmentally relevant conditions (i.e., aqueous solutions with irradiation wavelengths >290 nm) are included. Comparisons are made between observed photodegradation rates in pure or buffered water and in water containing DOM to assess the extent of pesticide susceptibility to DOM-sensitized indirect photolysis. When data is available, the role of specific reactive species in indirect photodegradation is described. While it is possible to assess the relative importance of direct and indirect photodegradation on a pesticide-by-pesticide basis in many cases, it is often difficult to make generalizations based on compound class. Knowledge gaps and inconstancies in the current body of literature are discussed and areas that require additional research are described.

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Photolysis of the herbicide sulcotrione: formation of a major photoproduct and its toxicity evaluation

Abstract: On irradiation, sulcotrione mainly gives the photocyclization product, which presents a higher toxicity than sulcotrione and CMBA. This cyclization product should thus be considered in sulcotrione environmental risk assessment.

Cited by 21 publications

References 15 publications

Atrazine, triketone herbicides, and their degradation products in sediment, soil and surface water samples in Poland

Atrazine, triketone herbicides, and their degradation products in sediment, soil and surface water samples in Poland

Transformation of the Herbicide Sulcotrione into a Root Growth Enhancer Compound by Sequential Photolysis and Hydrolysis

The role of indirect photochemical degradation in the environmental fate of pesticides: a review

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