Insights into the toxicity and biodegradation of fipronil in contaminated environment

Bhatt, Pankaj; Gangola, Saurabh; Ramola, Sudipta; Bilal, Muhammad; Bhatt, Kalpana; Huang, Yaohua; Zhou, Zhe; Chen, Shaohua

doi:10.1016/j.micres.2022.127247

Cited by 38 publications

(23 citation statements)

References 207 publications

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“…In soil, its half-life varies depending on the soil conditions, the microorganisms present in the medium, and the presence of oxygen [3], [4]. Its mode of action is selective towards insects and non-mammals, and it affects their nervous system by contact or ingestion, causing everything from excitement and convulsions to death due to disruption of the central nervous system [5]. On the other hand, the development of resistance to this pesticide in the target organisms has not been documented.…”

Section: Introductionmentioning

confidence: 99%

Characterization of Fipronil in Micellar Medium with Brij 35

Reyes-Sánchez,

Velázquez-Manzanares,

Gutiérrez-Ortiz

et al. 2024

EJCHEM

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Fipronil is a phenyl pyrazole used as an insecticide to combat termites, moths, and locusts. Its low solubility in water represents a problem with its commercial formulations. In this work, an aqueous micellar medium was formed with Brij 35, calculating the critical micellar concentration at 0.01% (w/v) by UV-visible spectrophotometry and conductimetry. In this medium, the apparent pka was estimated at 12.6 from spectrophotometric data by the graphical method and Partial Least Squares Regression. Finally, its degradation kinetics in this medium at pH 12 was studied, finding that it conforms to a first-order model, with a half-life of 3.3 h, higher than the 2.4 h reported by other authors for an aqueous medium. In conclusion, the micellar medium favored the solubility of the compound in aqueous medium, allowing the estimation of its pka and retarding its chemical degradation.

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Section: Introductionmentioning

confidence: 99%

Characterization of Fipronil in Micellar Medium with Brij 35

Reyes-Sánchez,

Velázquez-Manzanares,

Gutiérrez-Ortiz

et al. 2024

EJCHEM

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“…N -Phenylpyrazole derivatives have been reported to possess diversiform biological activities in the pharmaceutical and agrochemical fields. − Various molecules containing this motif are successfully developed as insecticides, acaricides, and herbicides in agriculture. In particular, N -phenylpyrazoles bearing a cyanide group on 3 position, a sulfinyl or thioalkyl group on 4 position, and an amino (or substituted amino) on 5 position of the pyrazole ring exhibit potent insecticidal activity. , For instance, fipronil, as the first marketed phenylpyrazole insecticide, has been widely used in crop protection and hygiene pest control for its excellent and broad-spectrum bioactivity, and no cross-resistance with other insecticidal agents. , The proven activity of fipronil is due to the affinity on the gamma-aminobutyric acid receptors (GABARs) and the inhibited influx of chloride ions by blocking the channels enclosed with the TM2 transmembrane helixes, thus causing neurological hyperexcitability and death of pests. − Although fipronil has a high selectivity between insects and mammals, potential toxicity risks to aquatic organisms and bees are also emphasized. − Consequently, the pesticide formulations containing fipronil have been banned in China since 2009, except for sanitary and dry field seed coating use. , Therefore, it is urgently necessary to develop low toxicity and high efficiency, as well as environmentally friendly, pesticide varieties through the modification of fipronil.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Bioactivity of Trifluoroethylthio-Substituted Phenylpyrazole Derivatives

Dong,

Wang,

Zhou

et al. 2024

J. Agric. Food Chem.

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As the first marketed phenylpyrazole insecticide, fipronil exhibited remarkable broad-spectrum insecticidal activity. However, it poses a significant threat to aquatic organisms and bees due to its high toxicity. Herein, 35 phenylpyrazole derivatives containing a trifluoroethylthio group on the 4 position of the pyrazole ring were designed and synthesized. The predicted physicochemical properties of all of the compounds were within a reasonable range. The biological assay results revealed that compound 7 showed 69.7% lethality against Aedes albopictus (A. albopictus) at the concentration of 0.125 mg/L. Compounds 7, 7g, 8d, and 10j showed superior insecticidal activity for the control of Plutella xylostella (P. xylostella). Notably, compound 7 showed similar insecticidal activity against Aphis craccivora (A. craccivora) compared with fipronil. Potential surface calculation and molecular docking suggested that different lipophilicity and binding models to the Musca domestica (M. domestica) gamma-aminobutyric acid receptors may be responsible for the decreased activity of the tested derivatives. Toxicity tests indicated that compound 8d (LC 50 = 14.28 mg/L) induced obviously 14-fold lower toxicity than fipronil (LC 50 = 1.05 mg/L) on embryonic-juvenile zebrafish development.

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“…The half-life of fipronil in aerobic soils is 122–128 days, and in water it is only 4–12 h when exposed to UV . Fipronil is metabolized in mammals by three main pathways, mainly through oxidation to form fipronil sulfone, reduction to form fipronil sulfide, and hydrolysis to first form fipronil amide and finally a carboxylic acid (5-amino-1-(2,6-dichloro-4-trifluoromethylphenyl) 4-trifluoromethyl sulfinyl pyrazole-3-carboxylic acid) after entering the body. − Humans are exposed to a mixture of FPM at low concentrations through daily drinking water and/or food. Therefore, the purpose of the present study is to identify whether FPM has adverse effects on human thyroid function.…”

Section: Introductionmentioning

confidence: 99%

Thyroid-Disrupting Effects of Exposure to Fipronil and Its Metabolites from Drinking Water Based on Human Thyroid Follicular Epithelial Nthy-ori 3-1 Cell Lines

Zhuang

Jiang

Chen

et al. 2023

Environ. Sci. Technol.

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Fipronil is a broad-spectrum insecticide used for plants and poultry. Owing to its widespread use, fipronil and its metabolites (fipronil sulfone, fipronil desulfinyl, and fipronil sulfide), termed FPM, can be frequently detected in drinking water and food. Fipronil can affect the thyroid function of animals, but the effects of FPM on the human thyroid remain unclear. We employed human thyroid follicular epithelial Nthy-ori 3-1 cells to examine combined cytotoxic responses, thyroid-related functional proteins including the sodium-iodide symporter (NIS), thyroid peroxidase (TPO), deiodinases I−III (DIO I−III), and the nuclear factor erythroid-derived factor 2−related factor 2 (NRF2) pathway induced by FPM of 1−1000-fold concentrations detected in school drinking water collected from a heavily contaminated area of the Huai River Basin. Thyroid-disrupting effects of FPM were evaluated by examining biomarkers of oxidative stress and thyroid function and tetraiodothyronine (T4) levels secreted by Nthy-ori 3-1 cells after FPM treatment. FPM activated the expression of NRF2, HO-1 (heme oxygenase 1), TPO, DIO I, and DIO II but inhibited NIS expression and increased the T4 level of thyrocytes, indicating that FPM can disrupt the function of human thyrocytes through oxidative pathways. Given the adverse impact of low FPM concentrations on human thyrocytes, supportive evidence from rodent studies, and the critical importance of thyroid hormones on development, the effects of FPM on the neurodevelopment and growth of children warrant priority attention.

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Insights into the toxicity and biodegradation of fipronil in contaminated environment

Cited by 38 publications

References 207 publications

Characterization of Fipronil in Micellar Medium with Brij 35

Characterization of Fipronil in Micellar Medium with Brij 35

Design, Synthesis, and Bioactivity of Trifluoroethylthio-Substituted Phenylpyrazole Derivatives

Thyroid-Disrupting Effects of Exposure to Fipronil and Its Metabolites from Drinking Water Based on Human Thyroid Follicular Epithelial Nthy-ori 3-1 Cell Lines

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