Ecotoxicity of the degradation products of triphenylborane pyridine (TPBP) antifouling agent

Triphenylborane pyridine (TPBP) is an alternative to organotin antifouling compounds. This work aimed to identify the unknown Peak #1, and to evaluate the ecotoxicity of TPBP and its degradation products. Peak #1 was produced from TPBP dissolved in acetonitrile under UV-A photolysis using a high-pressure mercury lamp. The Peak #1 fraction was purified using two-step column chromatography from a TPBP–acetonitrile solution. The major compound of the fraction was identified as being biphenyl from the 1H NMR and 13C NMR spectra. The ecotoxicity of four degradation products (diphenylborane hydroxide, phenylborane dihydroxide, phenol, and biphenyl) and TPBP towards two marine planktons were assessed. The 48 h LC50 values of the crustacean, Artemia salina, were 0.13 mg L−1 for TPBP, 14 mg L−1 for biphenyl, 17 mg L−1 for phenol, and >50 mg L−1 for the other degradation products. The 72 h EC50 values of the diatom, Skeletonema costatum, were 0.0022 mg L−1 for TPBP, 1.2 mg L−1 for biphenyl, and >2 mg L−1 for the other degradation products. Thus, the ecotoxicity of biphenyl and the other degradation products were not high compared to the parent compound, TPBP.