Revisiting pesticide pollution: The case of fluorinated pesticides

Alexandrino, Diogo A. M.; Almeida, C. Marisa R.; Mucha, Ana P.; Carvalho, Maria F.

doi:10.1016/j.envpol.2021.118315

Cited by 46 publications

(24 citation statements)

References 114 publications

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“…Fluorinated pesticides have an emerging role in the agrochemical market during the last decade. More notably, fluorine-containing pesticides accounted for almost 70% of the new agrochemicals approved between 2015 and 2020. , The introduction of fluorine can modulate the in vivo stereochemical behavior, lipophilicity, and stability, which results in the emergence of many beneficial properties, such as quick action, high selectivity, specificity, and prolonged residual activity . Modification of natural scaffolds with fluorine substitution was an efficient strategy to develop commercial pesticides; flupyradifurone and florylpicoxamid have been created recently following this strategy …”

Section: Resultsmentioning

confidence: 99%

Design, Synthesis, and Antifungal/Antioomycete Activity of Thiohydantoin Analogues Containing Spirocyclic Butenolide

Zhang

et al. 2023

J. Agric. Food Chem.

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Novel fungicidal agents were designed based on the combination of two privileged scaffolds, thiohydantoin and spirocyclic butenolide, which are widely found in natural products. The synthesized compounds were characterized by 1 H NMR, 13 C NMR, and high-resolution electrospray ionisation mass spectrometry. The in vitro antioomycete activity evaluation showed that most of the compounds exhibited excellent inhibitory activities against different developmental stages in the life cycle of pathogenic oomycete Phytophthora capsici. Compound 5j could inhibit the mycelial growth, sporangium production, zoospore release, and cystospore germination significantly with EC 50 values of 0.38, 0.25, 0.11, and 0.026 μg/mL, respectively. The in vivo antifungal/ antioomycete bioassay results revealed that the series of compounds generally showed outstanding control efficacies against the pathogenic oomycete Pseudoperonospora cubensis, and compounds 5j, 5l, 7j, 7k, and 7l possessed broad-spectrum antifungal activities against the test phytopathogens. The in vivo protective and curative efficacies against P. capsici of the representative compound 5j were excellent, which were better than those of azoxystrobin. More prominently, 5j significantly promoted the biomass accumulation of the root system and reinforced the cell wall by callose deposition. The pronounced upregulation of immune response-related genes indicated that the active oomycete inhibitor 5j also functioned as a plant elicitor. Transmission electron microscopy observation and the enzyme activity test demonstrated that the mechanism of action of 5j was to bind to the pivotal protein, complex III on the respiratory chain, which resulted in a shortage of energy supply. Molecular docking results exhibited that compound 5j appropriately matched with the Qo pocket and had no interaction with the most commonly mutated site Gly-142, which may be of significant benefit in Qo fungicide resistance management. Compound 5j showed great advantages and potential in oomycete control, resistance management, and induction of disease resistance. A further investigation of 5j with a unique structure might have direct implications for the creation of novel oomycete inhibitors against plant-pathogenic oomycetes.

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Section: Resultsmentioning

confidence: 99%

Design, Synthesis, and Antifungal/Antioomycete Activity of Thiohydantoin Analogues Containing Spirocyclic Butenolide

Zhang

et al. 2023

J. Agric. Food Chem.

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“…45 In fact, nearly 70 percent of all pesticides introduced into the global market from 2015 to 2020 contained fluorine. 46 Another possibility are fluorinated polymers, which are known to be used throughout consumer products, including cosmetic products, 47 and textiles. 48 Letcher et al 49 and Fredriksson et al 50 previously observed side-chain fluorinated polymers in sewage sludge at elevated concentrations, but only by using a substantially different extraction procedure (i.e.…”

Section: Characterization Of Standard Reference Materialsmentioning

confidence: 99%

Characterizing the Organohalogen Iceberg: Extractable, multi-halogen mass balance determination in municipal wastewater treatment plant sludge

Spaan

Yuan

Plassmann

et al. 2023

Preprint

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The large number and diversity of organohalogen compounds (OHCs) occurring in the environment poses a grand challenge to analytical chemists. Since no single targeted method can identify and quantify all OHCs, the size of the OHC iceberg may be underestimated. We sought to address this problem in municipal wastewater treatment plant (WWTP) sludge by quantifying the unidentified fraction of the OHC iceberg using targeted analyses of major OHCs together with measurements of total- and extractable (organo)halogen (TX and EOX, respectively; where X=F, Cl, or Br). In addition to extensive method validation via spike/recovery and combustion efficiency experiments, TX and/or EOX were determined in reference materials (BCR-461 and NIST SRMs 2585 and 2781) for the first time. Application of the method to WWTP sludge revealed that chlorinated paraffins (CPs) accounted for most (~92%) of the EOCl, while brominated flame retardants and per- and polyfluoroalkyl substances (PFAS) accounted for only 54% of the EOBr and 2% of the EOF, respectively. Moreover, unidentified EOF in non-polar CP extracts points to the existence of organofluorine(s) with physical-chemical properties unlike those of target PFAS. This study represents the first multi-halogen mass balance in WWTP sludge, and offers a novel approach to prioritization of sample extracts for follow-up investigation.

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“…In addition, diflufenican belongs to the group of fluorinated pesticides with a significant market share in the agricultural sector, and is one of the herbicides with the highest exceedance rate of the environmental quality standards in European surface waters. 38,39 2. Materials and method…”

Section: Introductionmentioning

confidence: 99%

Colloidal silica nanomaterials reduce the toxicity of pesticides to algae, depending on charge and surface area

Book

Persson

Carmona

et al. 2022

Environ. Sci.: Nano

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Revisiting pesticide pollution: The case of fluorinated pesticides

Cited by 46 publications

References 114 publications

Design, Synthesis, and Antifungal/Antioomycete Activity of Thiohydantoin Analogues Containing Spirocyclic Butenolide

Design, Synthesis, and Antifungal/Antioomycete Activity of Thiohydantoin Analogues Containing Spirocyclic Butenolide

Characterizing the Organohalogen Iceberg: Extractable, multi-halogen mass balance determination in municipal wastewater treatment plant sludge

Colloidal silica nanomaterials reduce the toxicity of pesticides to algae, depending on charge and surface area

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