Degradation of Kresoxim-Methyl in Water: Impact of Varying pH, Temperature, Light and Atmospheric CO2 Level

Khandelwal, Ashish; Gupta, Suman; Gajbhiye, V. T.; Varghese, Eldho

doi:10.1007/s00128-015-1627-0

Cited by 8 publications

(6 citation statements)

References 14 publications

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“…Differing from the other strobilurin fungicides such as azoxystrobin , and kresoxim-methyl, 1 possesses a unique methoxyacetamide moiety instead of the conventional methoxyacrylate or methoxyiminoacetate structure. The absence of acrylate or imino double bond in 1 resulted in the differential photodegradation profiles in water.…”

Section: Discussionmentioning

confidence: 99%

Photodegradation of Strobilurin Fungicide Mandestrobin in Water

Adachi

Suzuki

Nishiyama

et al. 2018

J. Agric. Food Chem.

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Photodegradation of a new strobilurin fungicide, mandestrobin, was investigated in buffered aqueous solution and synthetic humic water (SHW) under continuous irradiation with artificial sunlight (λ > 290 nm). In both aquatic media, the direct photolysis preferentially proceeded via homolytic bond cleavage at the benzyl phenyl ether, and the subsequent recombination of geminate radicals in a solvent cage gave the photo-Claisen rearrangement products. A radical mechanism in the photochemical rearrangement was strongly supported by a radical-trapping technique using a novel nitroxide spin label combined with electron spin resonance (ESR) and liquid chromatography-mass spectrometry (LC-MS) analyses. Photosensitized generation of hydroxyl radical in SHW might significantly contribute to enhancing the formation of a benzyl alcohol derivative. The series of photolysis products steadily degraded and finally mineralized to carbon dioxide.

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Section: Discussionmentioning

confidence: 99%

Photodegradation of Strobilurin Fungicide Mandestrobin in Water

Adachi

Suzuki

Nishiyama

et al. 2018

J. Agric. Food Chem.

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“…AZOX concentration decreased with time for all formulations, and all degradation kinetics followed a first-order model (Figure and Table ; R > 0.9876, P < 0.05). Hydrolysis is expected to be the main degradation mechanism at pH 8 . The first-order degradation rate constant ( k ) determined from the slope (absolute value) of the linear fit ranged from 0.0026 ± 0.0002 min –1 for the conventional formulation to 0.0028 ± 0.0002 min –1 for AZOX encapsulated in nSiO 2 , and to 0.002 ± 0.0002 min –1 for AZOX encapsulated in Allosperse.…”

Section: Resultsmentioning

confidence: 99%

“…Hydrolysis is expected to be the main degradation mechanism at pH 8. 35 The first-order degradation rate constant (k) determined from the slope (absolute value) of the linear fit ranged from 0.0026 ± 0.0002 min −1 for the conventional formulation to 0.0028 ± 0.0002 min −1 for AZOX encapsulated in nSiO 2 , and to 0.002 ± 0.0002 min −1 for AZOX encapsulated in Allosperse. In the equation, the slope for the Allosperse (0.002) was significantly lower than that of the conventional pesticide (0.0026) or nSiO 2 (0.0028).…”

Section: Thermal Degradation Kinetics Of Azoxystrobin Inmentioning

confidence: 98%

Thermal Degradation of Conventional and Nanoencapsulated Azoxystrobin due to Processing in Water, Spiked Strawberry, and Incurred Strawberry Models

Wang

Gravel

Bueno

et al. 2022

ACS Agric. Sci. Technol.

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Nanoencapsulated formulations of pesticides have been recently developed, and some products are now marketed for specific applications in agriculture. Pesticide residues present in raw agricultural products can degrade or react during food processing steps. To date, the fate of nanopesticides during food processing has not been well described. In this study, the thermal degradation of azoxystrobin (AZOX) in conventional and nanoencapsulated (Allosperse and nSiO 2 ) formulations was first assessed in water, spiked strawberry, and incurred strawberry models. The thermal degradation followed first-order kinetics when heated at 100 °C in the water model. The thermal degradation of AZOX in nanoformulations in strawberry models (18% AZOX decrease) was comparable to or lower than in the conventional formulation (21%), possibly due to the nanocarriers protecting the active ingredient from hydrolytic degradation. Out of 32 thermal degradation products (TDPs), only two were detected in both the spiked water and strawberry models, indicating differences in the thermal degradation reactions for AZOX in these two models. Identical TDPs were detected for both conventional and nanoformulations for each specific model, except for the absence of one (TDP22) in the nSiO 2 formulations. The nanoencapsulation of AZOX did not result in new TDPs in any of the matrices. Only six of the TDPs detected in water, four in spiked strawberries, and two in incurred strawberries have been previously reported in environmental studies on the metabolism of AZOX. Based on the observed TDPs, AZOX thermal degradation pathways include ether cleavage, hydrolysis, demethylation, and decarboxylation. Overall, although nanocarriers have no impact on the degradation product types, nanocarriers had a slight but significant impact on the degradation rate of pesticide active ingredients.

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“…Azoxystrobin metabolism is similar to the degradation of methoxyiminoacetate (Balba, 2007) and the fate of trifloxystrobin in plants and kresoxim-methyl in soils, plants, and rats. Khandelwal et al (2016) and light in aqueous conditions and revealed that it readily forms acid metabolites. The study emphasized that abiotic factors have significant effects on the dissipation of kresoxim-methyl under aqueous conditions.…”

Section: Physicochemical Transformation Of Strobilurinsmentioning

confidence: 99%

“…found that the photochemical reactivity of azoxystrobin was enhanced as the solvent polarity decreased. This phenomenon indicates that the accumulation of azoxystrobin tends to occur inside the cuticle, where it is photodegraded, or at the surface of crop leaves.Azoxystrobin metabolism is similar to the degradation of methoxyiminoacetate(Balba, 2007) and the fate of trifloxystrobin in plants and kresoxim-methyl in soils, plants, and rats Khandelwal et al (2016). investigated the persistence of kresoximmethyl at different temperatures, pH, atmospheric CO 2 levels…”

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confidence: 99%

An Overview of Strobilurin Fungicide Degradation:Current Status and Future Perspective

et al. 2020

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Strobilurin fungicides have been widely used in agricultural fields for decades. These pesticides are designed to manage fungal pathogens, although their broad-spectrum mode of action also produces non-target impacts. Therefore, the removal of strobilurins from ecosystems has received much attention. Different remediation technologies have been developed to eliminate pesticide residues from soil/water environments, such as photodecomposition, ozonation, adsorption, incineration, and biodegradation. Compared with conventional methods, bioremediation is considered a cost-effective and ecofriendly approach for the removal of pesticide residues. Several strobilurindegrading microbes and microbial communities have been reported to effectively utilize pesticide residues as a carbon and nitrogen source. The degradation pathways of strobilurins and the fate of several metabolites have been reported. Further indepth studies based on molecular biology and genetics are needed to elaborate their role in the evolution of novel catabolic pathways and the microbial degradation of strobilurins. The present review summarizes recent progress in strobilurin degradation and comprehensively discusses the potential of strobilurin-degrading microorganisms in the bioremediation of contaminated environments.

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Degradation of Kresoxim-Methyl in Water: Impact of Varying pH, Temperature, Light and Atmospheric CO2 Level

Cited by 8 publications

References 14 publications

Photodegradation of Strobilurin Fungicide Mandestrobin in Water

Photodegradation of Strobilurin Fungicide Mandestrobin in Water

Thermal Degradation of Conventional and Nanoencapsulated Azoxystrobin due to Processing in Water, Spiked Strawberry, and Incurred Strawberry Models

An Overview of Strobilurin Fungicide Degradation:Current Status and Future Perspective

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