Identification of photoproducts of fungicide cyprodinil and elucidation of transformation mechanism in water using LC-IT-TOF-MS/MS technique

Chen, Xiaoxin; Dong, Bizhang; Lin, Hongfang; Hu, Jiye

doi:10.1016/j.chemosphere.2016.05.036

Cited by 22 publications

(5 citation statements)

References 34 publications

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“…Extensive use of pesticides leads to their residues ending up in aquatic environments, posing serious health problems for humans and aquatic life. , Hence, performing a risk assessment and determining the potential adverse effects of pesticides are critical. Pyraclostrobin and a mixture group at 1 μM induced a significant delay in the development of embryos and resulted in mortality at all time-points.…”

Section: Discussionmentioning

confidence: 99%

“…Pesticides are used to control pests and diseases in agricultural applications to increase the yield and quality of the products . Extensive use of pesticides results in their residues ending up in the environment, including soil and water systems, which subsequently causes several health problems. , Every year, approximately 2.5 million tons of pesticides are leached out into the environment worldwide . According to the World Health Organization, unintentional poisonings are commonly associated with excessive use of and exposure to pesticides, and this causes approximately 355,000 global death yearly…”

Section: Introductionmentioning

confidence: 99%

“…2,3 Hence, performing a risk assessment and determining the potential adverse effects of h i b i t e d .…”

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confidence: 99%

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In Vitro, In Vivo, and In Silico Analysis of Pyraclostrobin and Cyprodinil and Their Mixture Reveal New Targets and Signaling Mechanisms

Kim,

Bereketoglu,

Sercinoglu

et al. 2024

Chem. Res. Toxicol.

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Pyraclostrobin and cyprodinil are broad-spectrum fungicides that are used in crops to control diseases. However, they are excessively used and, as a result, end up in the environment and threaten human health and ecosystems. Hence, knowledge of their mechanisms of action is critical to revealing their environmental fate and negative effects and regulating their use. In the present study, we conducted a comprehensive study to show the adverse effects of pyraclostrobin, cyprodinil, and their mixture using zebrafish larvae and different cell lines. Several end points were investigated, including mortality, development, gene expression, reporter assays, and molecular docking simulations. We found that both compounds and their mixture caused developmental delays and mortality in zebrafish, with a higher effect displayed by pyraclostrobin. Both compounds altered the expression of genes involved in several signaling pathways, including oxidative stress and mitochondrial function, lipid and drug metabolisms, the cell cycle, DNA damage, apoptosis, and inflammation. A noteworthy result of this study is that cyprodinil and the mixture group acted as NFκB activators, while pyraclostrobin demonstrated antagonist activity. The AHR activity was also upregulated by cyprodinil and the mixture group; however, pyraclostrobin did not show any effect. For the first time, we also demonstrated that pyraclostrobin had androgen receptor antagonist activity.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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In Vitro, In Vivo, and In Silico Analysis of Pyraclostrobin and Cyprodinil and Their Mixture Reveal New Targets and Signaling Mechanisms

Kim,

Bereketoglu,

Sercinoglu

et al. 2024

Chem. Res. Toxicol.

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“…, in which FeOH 2+ could be photo-active to the decay of PRO and TET due to the photo-generated hydroxyl radicals (Chen et al 2016). However, this photosensitization was almost not reflected in DIN degradation ( Fig.…”

Section: +mentioning

confidence: 97%

Degradation pathway of triazole fungicides and synchronous removal of transformation products via photo-electrocatalytic oxidation tandem MoS2 adsorption

Wang

Chen

Sun

et al. 2021

Environ Sci Pollut Res

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A simple and effective tandem process of photo-electrocatalytic oxidation (PECO)-MoS2 adsorption was developed for the synchronous removal of triazole fungicides (TFs) and toxicological transformation products (TPs). In order to accurately identify trace TPs and evaluate degradation pathway during water treatment, a sensitive analytical method was developed on the basis of the stir bar sorptive extraction (SBSE) pretreatment tandem LC-MS/MS technique. Firstly, the typical TFs (PRO, TET, and DIN, C0 = 1.0 mg/L) in actual water samples were treated under the optimal process (bias voltage 1.8 V, pH 4, irradiation intensity 50 mW/cm2, 0.05 g MoS2/100 mL, 350 rpm, adsorption of 5 min). The result indicated that the residues of PRO, TET, and DIN in secondary effluent were 0.0973, 0.0617, and 0.0012 mg/L, respectively, with the removal rates of 90.3%, 93.8%, and 99.9%, respectively, undergoing 30-min photo-electrocatalysis and 5-min adsorption. The alkaline medium was favorable for the adsorption of MoS2 to TFs. The assessment results of potential cancer risk indicated that the residues of TFs in secondary effluent were safe for drinking water consumption. Besides, the major TPs were identified via the SBSE-HRLC-MS/MS technique, and one possible transformation pathway of TFs was proposed. TFs mainly underwent dehydrochlorination, cyclization, hydroxylation, etc. to produce a series of nitrogenous heterocyclic compounds that possess higher polarity than parents, hinting that TPs might pose potential aquatic toxicity. However, TPs can be removed synchronously by this tandem technique. The current study can provide a theoretical basis for the harmless treatment of TFs in the water environment.

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“…One of the environmental pollutants associated with the factors mentioned above is cyprodinil, a pyrimidine amine pesticide widely used in the cultivation of vegetables, fruits, and rice. Its widespread use is driven by its effectiveness in combating gray mold in agricultural settings (Chen et al, 2016). Notably, cyprodinil has been detected in aquatic environments at concentrations ranging from 0.73 µg/L to 2.89 µg/L, indicating its potential for environmental exposure (Tang et al, 2020).…”

Section: Introductionmentioning

confidence: 99%

(−)‐Epicatechin gallate ameliorates cyprodinil‐induced cardiac developmental defects through inhibiting aryl hydrocarbon receptor in zebrafish

Huang,

Su,

et al. 2024

Birth Defects Research

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BackgroundCyprodinil is a widely used fungicide with broad‐spectrum activity, but it has been associated with cardiac abnormalities. (−)‐Epicatechin gallate (ECG), a natural polyphenolic compound, has been shown to possess protective properties in cardiac development.MethodsIn this study, we investigated whether ECG could mitigate cyprodinil‐induced heart defects using zebrafish embryos as a model. Zebrafish embryos were exposed to cyprodinil with or without ECG.ResultsOur results demonstrated that ECG significantly improved the survival rate, embryo movement, and hatching delay induced by cyprodinil. Furthermore, ECG effectively ameliorated cyprodinil‐induced cardiac developmental toxicity, including pericardial anomaly and impairment of cardiac function. Mechanistically, ECG attenuated the cyprodinil‐induced alterations in mRNA expression related to cardiac development, such as amhc, vmhc, tbx5, and gata4, as well as calcium ion channels, such as ncx1h, atp2a2a, and cdh2. Additionally, ECG was found to inhibit the activity of the aryl hydrocarbon receptor (AhR) signaling pathways induced by cyprodinil.ConclusionsIn conclusion, our findings provide evidence for the protective effects of ECG against cyprodinil‐induced cardiac developmental toxicity, mediated through the inhibition of AhR activity. These findings contribute to a better understanding of the regulatory mechanisms and safe utilization of pesticide, such as cyprodinil.

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Identification of photoproducts of fungicide cyprodinil and elucidation of transformation mechanism in water using LC-IT-TOF-MS/MS technique

Cited by 22 publications

References 34 publications

In Vitro, In Vivo, and In Silico Analysis of Pyraclostrobin and Cyprodinil and Their Mixture Reveal New Targets and Signaling Mechanisms

In Vitro, In Vivo, and In Silico Analysis of Pyraclostrobin and Cyprodinil and Their Mixture Reveal New Targets and Signaling Mechanisms

Degradation pathway of triazole fungicides and synchronous removal of transformation products via photo-electrocatalytic oxidation tandem MoS2 adsorption

(−)‐Epicatechin gallate ameliorates cyprodinil‐induced cardiac developmental defects through inhibiting aryl hydrocarbon receptor in zebrafish

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