Insight into the uptake and metabolism of a new insecticide cyetpyrafen in plants

Li, Runan; Wang, Sijia; Chang, Jinhe; Pan, Xinglu; Dong, Fengshou; Li, Zhiyuan; Zheng, Yongquan; Li, Yuanbo

doi:10.1016/j.envint.2022.107522

Cited by 31 publications

(12 citation statements)

References 67 publications

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“… Further, experimental K D values for lettuce roots were low for all compounds (0.05–0.7 L g –1 ), (Table S13) indicating that the translocation was not entirely hindered by sorption of the compounds to the root tissue and that these TWP-derived compounds can passively transit the plasma membranes without the need of secondary active transport mechanisms. Active transport was found to not be a significant contributor to translocation of cyetpyrafen . On the other hand, uptake of benzotriazole and 2-mercaptobenzothiazole into Arabidopsis plants was shown to exceed the transpiration stream by far. , Thus, the fast uptake of BTZ in lettuce plants (Figure ) may be partly attributed to the contribution of active transporter proteins.…”

Section: Resultsmentioning

confidence: 87%

“…Active transport was found to not be a significant contributor to translocation of cyetpyrafen. 32 On the other hand, uptake of benzotriazole and 2-mercaptobenzothiazole into Arabidopsis plants was shown to exceed the transpiration stream by far. 25 , 26 Thus, the fast uptake of BTZ in lettuce plants ( Figure 1 ) may be partly attributed to the contribution of active transporter proteins.…”

Section: Resultsmentioning

confidence: 99%

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Uptake, Metabolism, and Accumulation of Tire Wear Particle-Derived Compounds in Lettuce

Castan

Sherman

Peng

et al. 2022

Environ. Sci. Technol.

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Tire wear particle (TWP)-derived compounds may be of high concern to consumers when released in the root zone of edible plants. We exposed lettuce plants to the TWP-derived compounds diphenylguanidine (DPG), hexamethoxymethylmelamine (HMMM), benzothiazole (BTZ), N-phenyl-N′-(1,3-dimethylbutyl)-p-phenylenediamine (6PPD), and its quinone transformation product (6PPD-q) at concentrations of 1 mg L–1 in hydroponic solutions over 14 days to analyze if they are taken up and metabolized by the plants. Assuming that TWP may be a long-term source of TWP-derived compounds to plants, we further investigated the effect of leaching from TWP on the concentration of leachate compounds in lettuce leaves by adding constantly leaching TWP to the hydroponic solutions. Concentrations in leaves, roots, and nutrient solution were quantified by triple quadrupole mass spectrometry, and metabolites in the leaves were identified by Orbitrap high resolution mass spectrometry. This study demonstrates that TWP-derived compounds are readily taken up by lettuce with measured maximum leaf concentrations between ∼0.75 (6PPD) and 20 μg g–1 (HMMM). Although these compounds were metabolized in the plant, we identified several transformation products, most of which proved to be more stable in the lettuce leaves than the parent compounds. Furthermore, continuous leaching from TWP led to a resupply and replenishment of the metabolized compounds in the lettuce leaves. The stability of metabolized TWP-derived compounds with largely unknown toxicities is particularly concerning and is an important new aspect for the impact assessment of TWP in the environment.

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Section: Resultsmentioning

confidence: 87%

Section: Resultsmentioning

confidence: 99%

Uptake, Metabolism, and Accumulation of Tire Wear Particle-Derived Compounds in Lettuce

Castan

Sherman

Peng

et al. 2022

Environ. Sci. Technol.

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“…The specific chromatogram and fragmentation spectra are shown in Figures S5–S16. As the authentic standards were not available for most of the identified transformation products, considering their similar core structures and the same analytical conditions between parents and the products, peak areas were thus used for their relative quantification . The relative areas of these transformation products with their parents in the greenhouse PM are presented in Figure S3.…”

Section: Results and Discussionmentioning

confidence: 99%

Pesticides in Greenhouse Airborne Particulate Matter: Occurrence, Distribution, Transformation Products, and Potential Human Exposure Risks

Gao,

Wang,

et al. 2024

Environ. Sci. Technol.

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Pesticides are frequently sprayed in greenhouses to ensure crop yields, where airborne particulate matter (PM) may serve as a carrier in depositing and transporting pesticides. However, little is known about the occurrence and fate of PMborne pesticides in greenhouses. Herein, we examined the distribution, dissipation, and transformation of six commonly used pesticides (imidacloprid, acetamiprid, prochloraz, triadimefon, hexaconazole, and tebuconazole) in greenhouse PM (PM 1 , PM 2.5 , and PM 10 ) after application as well as the associated human exposure risks via inhalation. During 35 days of experiment, the six pesticides were detected in all PM samples, and exhibited size-and time-dependent distribution characteristics, with the majority of them (>64.6%) accumulated in PM 1 . About 1.0−16.4% of initially measured pesticides in PM remained after 35 days, and a total of 12 major transformation products were elucidated, with six of them newly identified. The inhalation of PM could be an important route of human exposure to pesticides in the greenhouse, where the estimated average daily human inhalation dose (ADD inh ) of the six individual pesticides was 2.1−1.2 × 10 4 pg/kg day −1 after application (1−35 days). Our findings highlight the occurrence of pesticides/transformation products in greenhouse PM, and their potential inhalation risks should be further concerned.

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“…Cyetpyrafen ( 43) was announced by Sinochem International Crop Care Company, Ltd. as a new acaricide in 2020. 6 It is an inhibitor of succinate dehydrogenase (complex II in the respiratory chain), 56,57 as also the closely related earlier product cyenopyrafen (44) (Figure 8). 58 It is mainly used against spider mites, especially Tetranychus urticae (two-spotted spider mite) 59,60 and Tetranychus cinnabarinus (carmine spider mite), 61,62 Panonychus citri (citrus red mite), 62 but also to control coccinellid beetles and is mainly applied in crops such as apples, citrus and strawberries.…”

Section: Cyetpyrafen (43)mentioning

confidence: 99%

“…Cyclobutrifluram (55) can be seen as a conformationally locked analog of fluopyram ( 56), 70 which also has fungicidal and nematicidal activity (Figure 10). The synthesis of cyclobutrifluram (55) starts from 2,4dichlorophenylacetonitrile (57). Benzylic alkylation with 1,2-dibromoethane results in cyclization to give the cyclopropyl derivative 58.…”

Section: Cyclobutrifluram (55)mentioning

confidence: 99%

Synthetic Approaches to the 2019–2020 New Agrochemicals

et al. 2023

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Insight into the uptake and metabolism of a new insecticide cyetpyrafen in plants

Cited by 31 publications

References 67 publications

Uptake, Metabolism, and Accumulation of Tire Wear Particle-Derived Compounds in Lettuce

Uptake, Metabolism, and Accumulation of Tire Wear Particle-Derived Compounds in Lettuce

Pesticides in Greenhouse Airborne Particulate Matter: Occurrence, Distribution, Transformation Products, and Potential Human Exposure Risks

Synthetic Approaches to the 2019–2020 New Agrochemicals

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