UV characterization and photodegradation mechanism of the fungicide chlorothalonil in the presence and absence of oxygen

Cooke, María Victoria; Oviedo, M. Belén; Peláez, Walter José; Argüello, Gustavo A.

doi:10.1016/j.chemosphere.2017.08.111

Cited by 12 publications

(7 citation statements)

References 36 publications

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“…All photolysis reactions were followed by 1 H-NMR in deuterated acetonitrile and all of them unveiled the formation of acetic acid as the unique decomposition product ( 1 H-NMR and photolysis 1 H-NMR study of DHAA 1 spectra are given in Figures S4–S5 in Supplementary data). Additionally, the possible interaction of oxygen in the mechanism of photodegradation was analyzed via an indirect singlet oxygen measurement method with cysteine [ 33 ]. This essay confirmed that there was no energy transfer involved in the process and that neither the presence nor the absence of oxygen present a remarkable difference in the resulting product.…”

Section: Resultsmentioning

confidence: 99%

Photolysis, tautomerism and conformational analysis of dehydroacetic acid and a comparison with 2-hydroxyacetophenone and 2-acetyl-1,3-cyclohexanodione

Cooke

Chans

Argüello

et al. 2020

Heliyon

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The purpose of this work was to determine the tautomerism, the conformational analysis and photoreactivity of dehydroacetic acid (DHAA, 1 ). For that reason, the photolysis of DHAA ( 1 ) was performed at 254 nm and compared with two structurally similar compounds: 2-hydroxyacetophenone (HAP, 2 ) and 2-acetyl-1,3-cyclohexanodione (ACH, 3 ). We confirmed the degradation of 1 to acetic acid and we propose a mechanism on the assumption that a [2+2] cyclodimerization occurs (after UV light absorption) followed by some consecutive Norrish Type I cleavages, affording ketenes that end-up in acetic acid. The UV absorption study was conducted for all three compounds to gain insight about their electronic transitions, both experimentally and with computational simulations using TDDFT (B3LYP/6-31+G(d,p)) methods. A detailed analysis of the different tautomers and isomers that can be present in solution and the MOs involved in the electronic transitions was also achieved. The HOMO→LUMO transition was the least energetic optically active transition for 1 and 2 , whereas 3 was recognized to have a HOMO-1→LUMO transition. These transitions were all of n→π ∗ character.

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Section: Resultsmentioning

confidence: 99%

Photolysis, tautomerism and conformational analysis of dehydroacetic acid and a comparison with 2-hydroxyacetophenone and 2-acetyl-1,3-cyclohexanodione

Cooke

Chans

Argüello

et al. 2020

Heliyon

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“…[a,b] Compound Gas Phase [c] TEA [d] Acetone [e] ~E kJ mol [a] For more details, see supporting information. [b] B3LYP and CAMÀ B3LYP functional methods [38,39] in combination with the 6-311 + G(d,p) basis set. [c] Gas: ɛ = 1.0000, [d] TEA: ɛ = 2.3832, [e] Acetone: ɛ = 20.7 (Due to the NMR analysis).…”

Section: Discussionmentioning

confidence: 99%

Selective Synthesis using ETFBO: A New Strategy for the Preparation of Hexahydro‐1H‐pyrrolo[1,2‐c]imidazol‐1‐one.

et al. 2023

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In this work, we report the regiospecific and stereoselective synthesis of novel pyrrolo thioxoimidazolidinones with promising biological activities due to the inherent pharmaceutical properties of thioxoimidazolidinone core. The reaction of different thioxoimidazolidinones with trans‐4‐ethoxy‐1,1,1‐trifluorobut‐3‐en‐2‐one (ETFBO) yields bicyclic 1,3‐diaza heterocycles bearing the trifluoromethyl (CF3) moiety. Our investigation involved both depth experimental analysis and theoretical calculations to fathom out the mode of reaction of this building block and elucidate the underlying mechanism operating for the observed reactions. Remarkably, this unusual mechanism retained the ethanol moiety from the building block in the final products, deviating from conventional nucleophilic reactions reported in the literature.

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“…In presence of ROS, L-Cys yields the insoluble cystine (Cys-Cys) by the formation of a disulfide bridge, Equation 8. [36] We assayed this experiment using 5 d as a sensitizer to generate ROS. After the irradiation of an oxygenated solution of 5 d in presence of L-Cys, a precipitate was formed.…”

Section: Light-mediated Antimicrobial Activitymentioning

confidence: 99%

Sulfated and Oxygenated Imidazoline Derivatives: Synthesis, Antioxidant Activity and Light‐Mediated Antibacterial Activity

et al. 2020

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Imidazoline derivatives with different exocyclic substituents were simply prepared from common starting materials. The procedures were carried out in an eco‐friendly manner. The antioxidant activity of these derivatives was explored by different experimental assays, such as ABTS.+ and DPPH. scavenging assay, as well as reducing power assay. The structural differences are discussed in terms of the results. Sulfur analogs showed higher antioxidant activity than their oxygenated counterparts. The same tendency was observed in microbiological studies, in which the same imidazoline compounds were assayed for light‐mediated activity against of Staphylococcus aureus and Escherichia coli strains. A light‐enhanced activity was observed for almost all the sulfated imidazolines after exposure to UV‐A (400‐320 nm) light.

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UV characterization and photodegradation mechanism of the fungicide chlorothalonil in the presence and absence of oxygen

Cited by 12 publications

References 36 publications

Photolysis, tautomerism and conformational analysis of dehydroacetic acid and a comparison with 2-hydroxyacetophenone and 2-acetyl-1,3-cyclohexanodione

Photolysis, tautomerism and conformational analysis of dehydroacetic acid and a comparison with 2-hydroxyacetophenone and 2-acetyl-1,3-cyclohexanodione

Selective Synthesis using ETFBO: A New Strategy for the Preparation of Hexahydro‐1H‐pyrrolo[1,2‐c]imidazol‐1‐one.

Sulfated and Oxygenated Imidazoline Derivatives: Synthesis, Antioxidant Activity and Light‐Mediated Antibacterial Activity

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