Persistence behavior of metamifop and its metabolite in rice ecosystem

Barik, Suhrid Ranjan; Ganguly, Pritam; Patra, Sandip; Dutta, Swaraj Kumar; Goon, Arnab; Bhattacharyya, Anjan

doi:10.1016/j.chemosphere.2017.11.101

Cited by 14 publications

(5 citation statements)

References 17 publications

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“…Metamifop can be quickly degraded to several metabolites in plants, including N-(2-fluorophenyl)-2-(4-hydroxyphenoxy)-Nmethylpropionamide (HPPFMA), HPFMA, 4-(6-chlorobenzooxazol-2-yloxy)phenol (CBOP), and 6-chloro-3H-benzooxazol-2-one (6-CBO) (Figure 4A). [45][46][47] In this study, metamifop and its major metabolites, HPFMA and 6-CBO, were identified by LC-MS/MS with retention times of 1.22, 0.76, and 0.77 min, respectively (Figure 4B-D). However, 6-CBO could not be quantified absolutely.…”

Section: Metamifop Metabolism In S and R Plants Of E Glabrescensmentioning

confidence: 73%

“…As documented, metamifop can be rapidly degraded to HPPFMA, HPFMA, CBOP, 6-CBO, and several other metabolites, and HPPFMA and CBOP will be degraded further to yield HPFMA and 6-CBO, respectively (Figure 4A). 45,46 In this study, the amounts of metamifop and its major metabolites HPFMA and 6-CBO were each compared between the S and R plants at different times after herbicide treatment. Unexpectedly, no significant difference in the amount of metamifop was revealed between the two biotypes at each time point.…”

Section: Discussionmentioning

confidence: 99%

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Metamifop resistance in Echinochloa glabrescens via glutathione S‐transferases‐involved enhanced metabolism

Zhao

Jiang

et al. 2023

Pest Management Science

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BACKGROUND Echinochloa glabrescens Munro ex Hook. f. is one of the main Echinochloa spp. seriously invading Chinese rice fields and has evolved resistance to commonly used herbicides. Previously, an E. glabrescens population (LJ‐02) with suspected resistance to the acetyl‐CoA carboxylase (ACCase)‐inhibiting herbicide metamifop was collected. This study aimed to determine its resistance status to metamifop and investigate the internal molecular mechanisms of resistance. RESULTS Single‐dose testing confirmed that the LJ‐02 population had evolved resistance to metamifop. Gene sequencing and a relative expression assay of ACCase ruled out target‐site based resistance to metamifop in LJ‐02. Whole‐plant bioassays revealed that, compared with the susceptible population XZ‐01, LJ‐02 was highly resistant to metamifop and exhibited cross‐resistance to fenoxaprop‐P‐ethyl. Pretreatment with the known glutathione S‐transferase (GST) inhibitor, 4‐chloro‐7‐nitrobenzoxadiazole (NBD‐Cl), largely reversed the resistance to metamifop by approximately 81%. Liquid chromatography–tandem mass spectrometry analysis indicated that the metabolic rates of one of the major metabolites of metamifop, N‐(2‐fluorophenyl)‐2‐hydroxy‐N‐methylpropionamide (HPFMA), were up to 383‐fold faster in LJ‐02 plants than in XZ‐01 plants. There were higher basal and metamifop‐inducible GST activities toward 1‐chloro‐2,4‐dinitrobenzene (CDNB) in LJ‐02 than in XZ‐01. Six GST genes were metamifop‐induced and overexpressed in the resistant LJ‐02 population. CONCLUSION This study reports, for the first time, the occurrence of metabolic metamifop resistance in E. glabrescens worldwide. The high‐level metamifop resistance in the LJ‐02 population may mainly involve specific isoforms of GSTs that endow high catalytic activity and strong substrate specificity. © 2023 Society of Chemical Industry.

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Section: Metamifop Metabolism In S and R Plants Of E Glabrescensmentioning

confidence: 73%

Section: Discussionmentioning

confidence: 99%

Metamifop resistance in Echinochloa glabrescens via glutathione S‐transferases‐involved enhanced metabolism

Zhao

Jiang

et al. 2023

Pest Management Science

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“…By taking the logarithm (ln) in each side of the equation, this can be re-written as ln C t = ln C 0 − kt . The half-life ( t 1/2 ) value of flucetosulfuron can be calculated as: t 1/2 = ln 2/ k [ 26 ].…”

Section: Methodsmentioning

confidence: 99%

Photodegradation of Flucetosulfuron, a Sulfonylurea-Based Herbicide in the Aqueous Media Is Influenced by Ultraviolet Irradiation

Goon

Bhattacharyya

Ghosh

et al. 2021

JoX

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Photodegradation (photolysis) causes the breakdown of organic pesticides molecules by direct or indirect solar radiation energy. Flucetosulfuron herbicide often encounters water bodies. For this reason, it is important to know the behavior of the compound under these stressed conditions. In this context, photodegradation of flucetosulfuron, a sulfonylurea-based herbicide, has been assessed in aqueous media in the presence of photocatalyst TiO2 and photosensitizers (i.e., H2O2, humic acid, and KNO3) under the influence of ultraviolet (UV) irradiation. The influence of different water systems was also assessed during the photodegradation study. The photodegradation followed the first-order reaction kinetics in each case. The metabolites after photolysis were isolated in pure form by column chromatographic method and characterized using the different spectral data (i.e., XRD, IR, NMR, UV-VIS, and mass spectrometry). The structures of these metabolites were identified based on the spectral data and the plausible photodegradation pathways of flucetosulfuron were suggested. Based on the findings, photocatalyst TiO2 with the presence of ultraviolet irradiation was found effective for the photodegradation of toxic flucetosulfuron residues under aqueous conditions.

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“…The major metabolite N ‐(2‐fluorophenyl)‐2‐hydroxy‐ N ‐methyl‐propionamide of metamifop in E. crus‐galli has been detected using liquid chromatography mass spectrometry (LC–MS) . This hints at the hydrolysis stability of the N ‐methyl‐propionamide fragment in the molecule in comparison with methyl ester cleavage (Fig.…”

Section: Chiral Herbicidesmentioning

confidence: 99%

Current status of chirality in agrochemicals

Jeschke

2018

Pest Management Science

146

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The agrochemical industry is searching continuously for new pesticides to develop products that have optimal efficacy, lower application rates in the field, increased selectivity, favourable toxicological and environmental safety, enhanced user friendliness and better economic viability. One strategy by which to achieve these ambitious goals makes use of the unique properties of molecules containing asymmetric centres. In the past, many natural products and their congeners have been a source of inspiration in the design of new active ingredients, and the molecular structures of the resulting compounds have become increasingly complex; some 30% contain fragments with asymmetric centres. However, despite enormous progress in catalytic asymmetric processes over the past decade, few agrochemicals are produced in an enantiomerically pure or enriched form on an industrial scale. Since 2007, ∼ 43% of the 44 products launched (insecticides, acaricides, fungicides, nematicides and herbicides) contain one or more asymmetric centres in the molecule (∼ 47%) and most have been launched as racemic mixtures of enantiomers or diastereomers. This review provides an overview of the current status of chiral agrochemicals launched over the past 10 years and describes the inherently connected challenges of modern agricultural chemistry by managing important aspects resulting from the stereochemistry of these innovative products. © 2018 Society of Chemical Industry.

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Persistence behavior of metamifop and its metabolite in rice ecosystem

Cited by 14 publications

References 17 publications

Metamifop resistance in Echinochloa glabrescens via glutathione S‐transferases‐involved enhanced metabolism

Metamifop resistance in Echinochloa glabrescens via glutathione S‐transferases‐involved enhanced metabolism

Photodegradation of Flucetosulfuron, a Sulfonylurea-Based Herbicide in the Aqueous Media Is Influenced by Ultraviolet Irradiation

Current status of chirality in agrochemicals

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