The metabolite 3,4,3ʹ,4ʹ-tetrachloroazobenzene (TCAB) exerts a higher ecotoxicity than the parent compounds 3,4-dichloroaniline (3,4-DCA) and propanil

Xiao, Huang; Kuckelkorn, Jochen; Nüßer, Leonie; Floehr, Tilman; Hennig, Michael; Roß-Nickoll, Martina; Schäffer, Andreas; Hollert, Henner

doi:10.1016/j.scitotenv.2016.02.019

Cited by 18 publications

(5 citation statements)

References 125 publications

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“…38 Previous quantitative structure-activity relationship simulations with TCAB, a major DCA metabolite, have indicated that triggering of ERβ, mineralocorticoid, glucocorticoid, and progesterone receptor activities are expected. 39 Taken together, these findings strengthen the evidence of the endocrine disrupting effects of DCA and its alterations at the molecular level.…”

Section: Resultssupporting

confidence: 68%

Proteomics analysis of zebrafish larvae exposed to 3,4‐dichloroaniline using the fish embryo acute toxicity test

Vieira

Hissa

Souza

et al. 2020

Environmental Toxicology

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The zebrafish (Danio rerio) is a small teleost fish that is becoming increasingly popular in laboratories worldwide and several attributes have also placed the zebrafish under the spotlight of (eco)toxicological studies. Since the 1990s, international organizations such as ISO and OECD have published guidelines for the use of zebrafish in ecotoxicological assessment of environmental toxicants such as the Fish Embryo Acute Toxicity (FET) test, OECD n 236 guideline. This protocol uses 3,4-dichloroaniline (DCA), an aniline pesticide whose toxicity to fish species at early life stages is well known, as a positive control. Despite its use, little is known about its molecular mechanisms, especially in the context of the FET test. Therefore, this study aimed to investigate such changes in zebrafish larvae exposed to DCA (4 mg/L) for 96 hours using gelfree proteomics. Twenty-four proteins detected in both groups were identified as significantly affected by DCA exposure, and, when considering group-specific entities, 48 proteins were exclusive to DCA (group-specific proteins) while 248 were only detected in the control group. Proteins modulated by DCA treatment were found to be involved in metabolic processes, especially lipids and hormone metabolism (eg, Apoa1 and Apoa1b and vitelogenins), as well as proteins important for developmental processes and organogenesis (eg, Myhc4, Acta2, Sncb, and Marcksb). The results presented here may therefore provide a better understanding of the relationships between molecular changes and phenotype in zebrafish larvae treated with DCA, the reference compound of the FET test.

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Section: Resultssupporting

confidence: 68%

Proteomics analysis of zebrafish larvae exposed to 3,4‐dichloroaniline using the fish embryo acute toxicity test

Vieira

Hissa

Souza

et al. 2020

Environmental Toxicology

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“…3,4-dichlorothalonil (3,4-DCA) is the main degradation product of diuron [37] and endangers the growth and development of aquatic organisms [39][40][41]. 3,4-DCA has a high water solubility of 580 mg/L at 20 • C and an estimated half-life of 18 days.…”

Section: 4-dcamentioning

confidence: 99%

Booster Biocides Levels in the Major Blood Cockle (Tegillarca granosa L., 1758) Cultivation Areas along the Coastal Area of Peninsular Malaysia

Mukhtar

Zulkifli

Mohamat-Yusuff

et al. 2020

Water

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Booster biocides have been rapidly growing in use, mainly in the shipping industry and in agricultural activities. The use of booster biocides is known to cause adverse effects on marine ecosystems, such as by inhibiting the photosynthesis process in marine plants, and they have the potential to accumulate in marine organisms. In the present study, booster biocides of Irgarol 1051, diuron, 3,4-dichloroaniline (3,4-DCA) and chlorothalonil were measured in the major blood cockle (Tegillarca granosa) cultivation areas along the west coast of Peninsular Malaysia. The highest Irgarol 1051 mean was found in the blood cockle with a value of 98.92 ± 13.65 µg/kg in Kapar, Selangor, while the means of diuron and its metabolites and 3,4-DCA showed the highest values of 40.31 ± 7.61 and 41.42 ± 21.58 µg/kg in Kapar, Selangor and Sungai Ayam, Johor, respectively. Sungai Ayam, Johor also exhibited the highest amount of chlorothalonil of 29.76 ± 8.80 µg/kg. By referring to sediment quality guidelines, about 72% and more than 90% of sediment samples exceeded the environmental risk limits (ERLs) and maximum permissible concentration (MPC) for Irgarol 1051 and diuron, respectively. However, referring to the risk characterization ratio (RCR), none of the blood cockle samples exceeded 1, which means that there is no potential for adverse effects to occur. Thus, the contaminants in the marine ecosystem caused by booster biocides are highlighted as a serious issue, mainly in sediment.

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“…3,4-DCA is a precursor and intermediate in the chemical synthesis of a variety of phenylurea herbicides (e.g., diuron and linuron) and is also a primary metabolite of these pesticides in plants and the environment, with higher toxicity and longer persistence in the environment than parent compounds [5,6]. 3,4-DCA is a relatively mobile compound.…”

Section: Introductionmentioning

confidence: 99%

Development of Simultaneous Determination Method of Pesticide High Toxic Metabolite 3,4-Dichloroaniline and 3,5 Dichloroaniline in Chives Using HPLC-MS/MS

Dong,

Yao,

Zhang

et al. 2023

Foods

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3,4-dichloroaniline (3,4-DCA) and 3,5-dichloroaniline (3,5-DCA) are, respectively, the primary metabolites deriving from the breakdown of phenylurea herbicides and dicarboximide fungicides in both soils and plants, whose residues in vegetable products have a heightened concern considering their higher health risks to humans and greater toxicity than the parent compounds in the environment. In this study, a sensitive high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) method was developed for the simultaneous determination of 3,4-DCA and 3,5-DCA residues in chive products based on the optimization of HPLC-MS/MS chromatographic and mass-spectrometric conditions using the standard substances and the modified QuEChERS preparation technique. The preparation efficiency of 3,4-DCA and 3,5-DCA from chive samples showed that acetonitrile was the best extractant. The combination of the purification agent graphite carbon black + primary secondary amine and the eluting agent acetonitrile + toluene (4:1, v/v) had a satisfactory purification effect. The linear correlation coefficients (R2) were more than 0.996 with the six concentration range of 0.001–1.000 mg/L for 3,4-DCA and 3,5-DCA. The limit of detection and limit of quantitation of this method was 0.6 and 2.0 µg/kg for 3,4-DCA, as well as 1.0 and 3.0 µg/kg for 3,5-DCA, respectively. The matrix effect range of 3,4-DCA and 3,5-DCA in chive tissues was from −9.0% to −2.6% and from −4.4% to 2.3%, respectively. The fortified recovery of 3,4-DCA and 3,5-DCA in chive samples at four spiked levels of 0.001–1.000 mg/kg was 75.3–86.0% and 78.2–98.1%, with the relative standard deviation of 2.1–8.5% and 1.4–11.9%, respectively. The limit of detection (LOD) and limit of quantification (LOQ) of the method were 0.6, 2.0, and 1.0, 3.03 for 4-DCA and 3,5-DCA, respectively. This study highlights that the analytical method established here can efficiently and sensitively detect residues of 3,4-DCA and 3,5-DCA residues for monitoring chive products. The method was successfully applied to 60 batches of actual vegetable samples from different regions.

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The metabolite 3,4,3ʹ,4ʹ-tetrachloroazobenzene (TCAB) exerts a higher ecotoxicity than the parent compounds 3,4-dichloroaniline (3,4-DCA) and propanil

Cited by 18 publications

References 125 publications

Proteomics analysis of zebrafish larvae exposed to 3,4‐dichloroaniline using the fish embryo acute toxicity test

Proteomics analysis of zebrafish larvae exposed to 3,4‐dichloroaniline using the fish embryo acute toxicity test

Booster Biocides Levels in the Major Blood Cockle (Tegillarca granosa L., 1758) Cultivation Areas along the Coastal Area of Peninsular Malaysia

Development of Simultaneous Determination Method of Pesticide High Toxic Metabolite 3,4-Dichloroaniline and 3,5 Dichloroaniline in Chives Using HPLC-MS/MS

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