The photo-degradation of mesotrione, a triketone herbicide, in the presence of Cu II  ions

Person, A. Le; Siampiringue, Marie; Sarakha, Mohamed; Moncomble, Aurélien; Cornard, Jean-Paul

doi:10.1016/j.jphotochem.2015.09.010

Cited by 11 publications

(5 citation statements)

References 51 publications

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“…P2 which has a retention time of 3.3 minutes and C 8 H 7 O 5 Sas elemental composition lost the nitrogen atom. These products were already presented in the literature [2][3][4] and they correspond to the following structures (Scheme 5).…”

Section: Mass Spectra Analyses Of the Byproducts P1 P2 And P3mentioning

confidence: 84%

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Homolytic Scission as the Main Pathway in the Liquid Chromatography/ Electrospray Ionization Quadrupole Time-of-Flight Mass Spectrometry of Mesotrione and its Photoproducts

Chahboune¹,

Sarakha²

2018

Mass Spectrom Purif Tech

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The indirect photochemical degradation of mesotrione induced by humic substances was studied by excitation with a solar light simulator. The disappearance rate constant increased by increasing the concentration of molecular oxygen. Three main byproducts were observed. They all arise from the dissociation of the non-aromatic cycle. Collision-induced dissociation tandem mass spectrometry (CID-MS/MS) of the deprotonated molecule was carried out and the effect of the collision energy as well as the elemental compositions of the products ions was used to propose the chemical structures. The presence in the chemical structure of the SO2-Me moiety permitted several types of homolytic scissions leading to the formation of radical anions.

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Section: Mass Spectra Analyses Of the Byproducts P1 P2 And P3mentioning

confidence: 84%

“…It is supposed to act by competitive inhibition of the enzyme 4-hydroxyphenylpyruvate dioxygenase (HPPD) [2,3]. The fate of mesotrione under various environmental conditions has been the subject of several research activities [4][5][6][7][8]. As examples:…”

Section: Mesotrionementioning

confidence: 99%

Homolytic Scission as the Main Pathway in the Liquid Chromatography/ Electrospray Ionization Quadrupole Time-of-Flight Mass Spectrometry of Mesotrione and its Photoproducts

Chahboune¹,

Sarakha²

2018

Mass Spectrom Purif Tech

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“…Mesotrione, 2-(4-methylsulfonyl-2-nitrobenzoyl) cyclohexane-1,3-dione, is an organic compound classified as a triketone herbicide that is widely used in modern agriculture to control weeds and increase crop yields of corn (Mitchell et al, 2001). The coordination properties of triketone herbicides are dictated by the presence of three ketone functional groups, which act as ligands, forming stable coordination complexes with metal ions such as Cu 2+ , Co 2+ and Fe 3+ (Le Person et al, 2016). The stability of the chelates depends largely on the pH, as mesotrione is a weak acid that dissociates from the molecular to the anionic form at higher pH, which is more resistant to hydrolysis and photolysis processes (Reynolds et al, 2007).…”

Section: Chemical Contextmentioning

confidence: 99%

Crystal structure of the sodium salt of mesotrione: a triketone herbicide

Bereziuk,

Gubina,

Trush

et al. 2024

Acta Cryst E

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The crystal structure of the sodium salt of mesotrione, namely, catena-poly[[sodium-μ3-2-[(4-methanesulfonyl-2-nitrophenyl)carbonyl]-3-oxocyclohex-1-en-1-olato] ethanol monosolvate], {[Na(C14H12NO7S)]C2H5OH} n , is described. The X-ray structural analysis results reveal that the coordination sphere is established by two chelating O atoms, the O atom of the coordinated ethanol molecule, and an O atom from the methylsulfonyl group of a neighboring molecule. Simultaneously, an O atom of the cyclohexane fragment serves as a bridge to a neighboring sodium ion, forming a flat Na–O–Na–O quadrangle, thereby forming a mono-periodic polymer. The structure displays O—H...O hydrogen bonds and C—H...O short contacts. Thermogravimetric analysis (TGA) data indicate that the sodium salt of mesotrione decomposes in four stages.

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“…The thermodynamic data indicate that HIHs can be retained in soil with a pH range of 6.5−8.5 because of the formation of nonextractable residues or metal complexes. For example, Le Person et al reported the formation of mesotrione−Cu(II) complex, 16 whereas Hynes and Walsh observed a reaction between either Ni(II) or Co(II) and triketones. 17 The investigation of the reactivity of HIHs with more transition metal ions is still needed.…”

Section: Retention Of Hihs In Soilsmentioning

confidence: 99%

Advances in Understanding the Toxicity of 4-Hydroxyphenylpyruvate Dioxygenase-Inhibiting Herbicides

Ndikuryayo,

Gong,

Yang

2024

J. Agric. Food Chem.

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4-Hydroxyphenylpyruvate dioxygenase inhibiting herbicides (HIHs) represent a recent class (HRAC group 27) of herbicides that offer many advantages, such as broad-spectrum activity, crop selectivity, and low resistance rates. However, emerging studies have highlighted the potential toxicity of HIHs in the environment. This review aims to provide a comprehensive summary of the toxicity of HIHs toward nontarget organisms, including plants, microorganisms, animals, and humans. Furthermore, the present work discusses the ecological roles of these organisms in the environment and their significance in agriculture. By shedding light on the toxicity of HIHs, this study seeks to raise awareness among end users, including environmentalists, researchers, and farmers, regarding the potential ecological implications of these herbicides. Hopefully, this knowledge can contribute to informed decisionmaking and sustainable practices in green agriculture and environmental management.

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The photo-degradation of mesotrione, a triketone herbicide, in the presence of Cu II ions

Cited by 11 publications

References 51 publications

Homolytic Scission as the Main Pathway in the Liquid Chromatography/ Electrospray Ionization Quadrupole Time-of-Flight Mass Spectrometry of Mesotrione and its Photoproducts

Homolytic Scission as the Main Pathway in the Liquid Chromatography/ Electrospray Ionization Quadrupole Time-of-Flight Mass Spectrometry of Mesotrione and its Photoproducts

Crystal structure of the sodium salt of mesotrione: a triketone herbicide

Advances in Understanding the Toxicity of 4-Hydroxyphenylpyruvate Dioxygenase-Inhibiting Herbicides

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