Mechanism and kinetics of diuron oxidation by hydroxyl radical addition reaction

Manonmani, Gunasekaran; Sandhiya, L.; Senthilkumar, K.

doi:10.1007/s11356-020-07806-4

Cited by 17 publications

(13 citation statements)

References 41 publications

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“…The M06-2X method is known to be a more reliable method to calculate the energetics, thermochemistry, and kinetics of atmospheric chemical reactions. Previous studies from many research groups − and our group − showed that the results obtained from the M06-2X method are comparable with the available experimental results.…”

Section: Resultssupporting

confidence: 82%

“…To study the possibility of photolysis for sulfoxaflor and its oxidation products, the absorption spectra of sulfoxaflor and intermediate complexes IC1 – IC7 were calculated by employing the time-dependent DFT (TDDFT) method at the M06-2X , and the CAM-B3LYP methods with the 6-311+G(d,p) basis set, and the calculated absorption wavelength (λ), absorption energy ( T v ), orbital transitions, and oscillator strength ( f ) are summarized in Table S7. The simulated spectra are shown in Figure .…”

Section: Resultsmentioning

confidence: 99%

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Mechanism, Kinetics, and Ecotoxicity Assessment of ·OH-Initiated Oxidation Reactions of Sulfoxaflor

2021

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The •OH-initiated reaction mechanism and kinetics of sulfoxaflor were investigated by using electronic structure calculations. The possible hydrogen atom and cyano group abstraction reaction pathways were studied, and the calculated thermochemical parameters show that the hydrogen atom abstraction from the C7 carbon atom is the more favorable reaction pathway. The subsequent reactions for the favorable intermediate (I4) with other atmospheric reactive species, such as O 2 , H 2 O, HO 2 •, and NO x • (x = 1, 2), were studied in detail. The products identified from the subsequent reactions could contribute to secondary organic aerosol (SOA) formation in the atmosphere. The intermediates and products formed from the initial and subsequent reactions are equally as toxic as the parent sulfoxaflor. At 298 K, the rate constant calculated for the formation of the favorable intermediate I4 is 2.54 × 10 −12 cm 3 molecule −1 s −1 , which shows that the lifetime of sulfoxaflor is 54 h. The excited-state calculation performed through time-dependent density functional theory shows that the photolysis of the title molecule is unlikely in the atmosphere. The global warming potentials (GWPs) for different time horizons, photochemical ozone creation potential (POCP), and ecotoxicity analysis were also studied for the insecticide sulfoxaflor.

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Section: Resultssupporting

confidence: 82%

Section: Resultsmentioning

confidence: 99%

Mechanism, Kinetics, and Ecotoxicity Assessment of ·OH-Initiated Oxidation Reactions of Sulfoxaflor

2021

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“…This is corroborated by the fact that inhibitions are noted only with photosynthetic physiology (at the impingement of light, and not otherwise); a clear signal that supports the murburn proposal that DROS are the obligatory agents involved in the interactive scheme with these molecules. In this regard, the reactions of molecules like diuoron and paraquat are documented with DROS like hydroxyl or superoxide radicals (da Silva Simões et al, 2017;Manonmani et al, 2020). Therefore, this is strong evidence in support of the murburn perspective of Pl-Pp.…”

Section: A Survey and Analysis Of Various Types Of Inhibitors Of Pl-ppmentioning

confidence: 64%

Correlation of inhibitions to structural aspects of chloroplast proteins: A murburn perspective

Manoj¹,

Gideon²,

Nirusimhan³

2021

Preprint

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In this manuscript, we we first present a brief review of the structural awareness on chloroplasts, the two photosystems (PS I & PS II, along with the respective light harvesting complexes and chlorophyll binding proteins). Thereafter, with an in silico approach, we attempt to correlate the photoactive proteins’ inhibition by various class of molecules, particularly weedicides. The prevailing understanding relies on topographical-affinity driven binding based explanations for electron transfers and inhibitions. The murburn model of photosynthesis deems DROS (diffusible reactive oxygen species) mediated constructive outcomes as the physiological mechanism for overall outcomes. We unravel key anomalous observations on the inhibitory aspects of the photosynthetic machinery, which were also noted in DROS involving systems like microsomal xenobiotic metabolism and mitochondrial oxidative phosphorylation. Via a comparative logic and applying Ockham’s razor, we infer that inhibitory outcomes in several photolysis-photophosphorylation processes are better explained by the murburn model.

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“…Various technologies have emerged to remove DUR from the environment and reduce its harmful effects, including advanced physical adsorption, photocatalytic degradation, chemical degradation, and biological treatments (da Silva Teófilo et al, 2020;de Souza and Dos Santos, 2020;Park and Jhung, 2020;Silambarasan et al, 2020). However, previous studies have reported that the by-products of the abiotic transformation of this compound are more hazardous than the parent compound itself (Liu et al, 2018;Manonmani et al, 2020). Moreover, DUR can be released back into the soil after the formation of bound residues via physical adsorption (Dias Guimaraes et al, 2018).…”

Section: Introductionmentioning

confidence: 99%

“…Continuous use of DUR has resulted in the contamination of the environment and raised public concern about its impact on human health. In mammals, including humans, DUR (0.05–0.5 μg/L) is suspected of having carcinogenic, mutagenic, and neurotoxic effects, causing genotoxicity, cytotoxicity, embryotoxicity, and immunotoxicity, as well as a disruption of endocrine, respiratory, and cardiovascular processes ( da Rocha et al, 2013 ; Behrens et al, 2016 ; Manonmani et al, 2020 ). This compound (200 ng/L) is also harmful to fish, plants, aquatic invertebrates, freshwater algae, and microbial species ( Pesce et al, 2010 ; Pereira et al, 2015 ; Wilkinson et al, 2017 ; Pei et al, 2020 ).…”

Section: Introductionmentioning

confidence: 99%

Emerging Strategies for the Bioremediation of the Phenylurea Herbicide Diuron

Zhang

Lin

et al. 2021

Front. Microbiol.

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Diuron (DUR) is a phenylurea herbicide widely used for the effective control of most annual and perennial weeds in farming areas. The extensive use of DUR has led to its widespread presence in soil, sediment, and aquatic environments, which poses a threat to non-target crops, animals, humans, and ecosystems. Therefore, the removal of DUR from contaminated environments has been a hot topic for researchers in recent decades. Bioremediation seldom leaves harmful intermediate metabolites and is emerging as the most effective and eco-friendly strategy for removing DUR from the environment. Microorganisms, such as bacteria, fungi, and actinomycetes, can use DUR as their sole source of carbon. Some of them have been isolated, including organisms from the bacterial genera Arthrobacter, Bacillus, Vagococcus, Burkholderia, Micrococcus, Stenotrophomonas, and Pseudomonas and fungal genera Aspergillus, Pycnoporus, Pluteus, Trametes, Neurospora, Cunninghamella, and Mortierella. A number of studies have investigated the toxicity and fate of DUR, its degradation pathways and metabolites, and DUR-degrading hydrolases and related genes. However, few reviews have focused on the microbial degradation and biochemical mechanisms of DUR. The common microbial degradation pathway for DUR is via transformation to 3,4-dichloroaniline, which is then metabolized through two different metabolic pathways: dehalogenation and hydroxylation, the products of which are further degraded via cooperative metabolism. Microbial degradation hydrolases, including PuhA, PuhB, LibA, HylA, Phh, Mhh, and LahB, provide new knowledge about the underlying pathways governing DUR metabolism. The present review summarizes the state-of-the-art knowledge regarding (1) the environmental occurrence and toxicity of DUR, (2) newly isolated and identified DUR-degrading microbes and their enzymes/genes, and (3) the bioremediation of DUR in soil and water environments. This review further updates the recent knowledge on bioremediation strategies with a focus on the metabolic pathways and molecular mechanisms involved in the bioremediation of DUR.

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Mechanism and kinetics of diuron oxidation by hydroxyl radical addition reaction

Cited by 17 publications

References 41 publications

Mechanism, Kinetics, and Ecotoxicity Assessment of ·OH-Initiated Oxidation Reactions of Sulfoxaflor

Mechanism, Kinetics, and Ecotoxicity Assessment of ·OH-Initiated Oxidation Reactions of Sulfoxaflor

Correlation of inhibitions to structural aspects of chloroplast proteins: A murburn perspective

Emerging Strategies for the Bioremediation of the Phenylurea Herbicide Diuron

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