Tetrabromobisphenol A (TBBPA) is one of the most widely used brominated flame retardants (BFRs) and has been frequently detected in the environment and biota. Recent studies have found that derivatives of TBBPA, such as TBBPA bis(allyl) ether (TBBPA BAE) and TBBPA bis(2,3-dibromopropyl) ether (TBBPA BDBPE) are present in various environmental compartments. In this work, using liquid chromatography coupled with tandem mass spectrometry (LC−MS/MS) and liquid chromatography coupled with quadrupole time-of-flight mass spectrometry (LC−Q-TOF-MS), TBBPA allyl ether (TBBPA AE) and TBBPA 2,3-dibromopropyl ether (TBBPA DBPE) were identified in environmental samples and further confirmed by synthesized standards. Soil, sediment, rice hull, and earthworm samples collected near a BFR manufacturing plant were found to contain these two compounds. In sediments, the concentrations of TBBPA AE and TBBPA DBPE ranged from 1.0 to 346.6 ng/g of dry weight (dw) and from 0.7 to 292.7 ng/g of dw, respectively. TBBPA AE and TBBPA DBPE in earthworm and rice hull samples were similar to soil samples, which ranged from below the method limit of detection (LOD, <0.002 ng/g of dw) to 0.064 ng/g of dw and from below the LOD (<0.008 ng/g of dw) to 0.58 ng/g of dw, respectively. Furthermore, mollusks collected from the Chinese Bohai Sea were used as a bioindicator to investigate the occurrence and distribution of these compounds in the coastal environment. The detection frequencies of TBBPA AE and TBBPA DBPE were 41 and 32%, respectively, and the concentrations ranged from below LOD (<0.003 ng/g of dw) to 0.54 ng/g of dw, with an average of 0.09 ng/g of dw, for TBBPA AE, and from below LOD (<0.008 ng/g of dw) to 1.41 ng/g of dw, with an average of 0.15 ng/g of dw, for TBBPA DBPE.

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Polybrominated diphenyl ethers (PBDEs) are widely distributed persistent organic pollutants. In vitro and in vivo research using various animal models have shown that PBDEs might be transformed to hydroxylated PBDEs, but there are few studies on in vivo metabolism of PBDEs by intact whole plants. In this research, pumpkin plants (Cucurbita maxima × C. moschata) were hydroponically exposed to 2,2',4,4'-tetrabromodiphenyl ether (BDE-47). A debromination product (BDE-28) and four hydroxylated metabolites (5-OH-BDE-47, 6-OH-BDE-47, 4'-OH-BDE-49, and 4-OH-BDE-42) were detected in different parts of the whole plant. In addition, 4-methoxylated-2,2',3,4'-tetraBDE (4-MeO-BDE-42) was observed as a methoxylation product. Root exudates in solution were found to play an important role in metabolizing BDE-47 to a specific OH-PBDE: 4'-OH-BDE-49. BDE-28 was found to translocate more easily and accumulate in shoots than BDE-47 due to the lower hydrophobicity and molecular weight. The concentration ratio between metabolites and parent compound BDE-47 was lower for OH-PBDEs than that for both BDE-28 and 4-MeO-BDE-42. The metabolism pathway of BDE-47 in young whole plants was proposed in this study.