Photodegradation of mercaptopyridine-N-oxide biocides

Neihof, Rex A.; Bailey, Carmela A.; Patouillet, Constance; Hannan, Patrick J.

doi:10.1007/bf01056251

Cited by 30 publications

(12 citation statements)

References 9 publications

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“…The persistence of ZnPT 2 in natural waters is low because of its rapid photodegradation (Turley et al 2000), and ZnPT 2 has not been detected in aquatic environments to our knowledge. One study demonstrated the persistence of pyrithione in water (Mackie et al 2004) although another study revealed pyrithione underwent rapid reduction in toxicity upon exposure to sunlight (Neihof et al 1979). ZnPT 2 can transform into CuPT 2 by transchelation with the copper ion in the laboratory and under natural conditions (Grunnet and Dahllof 2005;Thomas 1999).…”

mentioning

confidence: 97%

“…The environmental effects of ZnPT 2 or CuPT 2 on microalgae, macrophytes, crustaceans, fish, sea urchin, and other organisms have been studied (Bao et al 2008;Bellas et al 2005;Goka 1999;Kobayashi and Okamura 2002;Koutsaftis and Aoyama 2006;Mochida et al 2006Mochida et al , 2008Myers et al 2006;Okamura et al 2002Okamura et al , 2003. However, only a few works have investigated the environmental toxicity of their degradation products (Mochida et al 2009(Mochida et al , 2011Neihof et al 1979;Onduka et al 2010). ZnPT 2 causes morphological abnormality in both killifish and zebrafish (Goka 1999).…”

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confidence: 98%

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Effects of metal pyrithione antifoulants on freshwater macrophyte Lemna gibba G3 determined by image analysis

et al. 2012

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Copper pyrithione (CuPT(2)) and zinc pyrithione (ZnPT(2)) are two popular antifouling agents that prevent biofouling. Research into the environmental effects of metal pyrithiones has mainly focused on aquatic animal species such as fish and crustaceans, and little attention has been paid to primary producers. There have been few reports on residues in environmental matrices because of the high photolabile characteristics of the agents. Residue analyses and ecological effects of the metabolites and metal pyrithiones are not yet fully understood. This study was undertaken to assess the effects of CuPT(2), ZnPT(2), and six metabolites (PT(2): 2,2'-dithio-bispyridine N-oxide, PS(2): 2,2'-dithio-bispyridine, PSA: pyridine-2-sulfonic acid, HPT: 2-mercaptopyridine N-oxide, HPS: 2-mercaptopyridine, and PO: pyridine N-oxide) on a freshwater macrophyte. A 7-day static bioassay using axenic duckweed Lemna gibba G3 was performed under laboratory conditions. Toxic effects of test compounds were assessed by biomass reduction and morphological changes were determined in image analysis. Concentrations of ZnPT(2) and CuPT(2) and those of PT(2) and HPT in the medium were determined by derivatizing 2,2'-dithio-bispyridine mono-N-oxide with pyridine disulfide/ethylene diamine tetra-acetic acid reagent that was equimolar with pyrithione. The toxic intensity of the compounds was calculated from the measured concentrations after 7-day exposure. ZnPT(2), CuPT(2), PT(2), and HPT inhibited the growth of L. gibba with EC(50) ranging from 77 to 140 μg/l as calculated from the total frond number as the conventional index, whereas the other four metabolites had less effect even at 10 mg/l. The presence of the former four toxic derivatives resulted in abnormally shaped and unhealthily colored fronds, whose size was about 20% of the control fronds. EC(50), calculated from the healthy frond area determined in image analysis, ranged from 10 to 53 μg/l. Thus, image analysis as part of a duckweed bioassay can detect the toxic effects of pyrithione derivatives with 3-10 times higher sensitivity than the traditional index.

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confidence: 97%

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confidence: 98%

Effects of metal pyrithione antifoulants on freshwater macrophyte Lemna gibba G3 determined by image analysis

et al. 2012

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“…The pyrithione complexes are neutral and hydrophobic, with a low solubility in water, resulting in a high affinity for organic matter. The pyrithione molecule can be photolysed at wavelengths between 320-355 nm (Neihof et al, 1979) or degraded by chemical or biological oxidation (Turley et al, 2000). Reported half-lives of ZnPT 2 and CuPT 2 vary between minutes to hours in water, whereas no studies have been made in sediments.…”

Section: Chemical Properties Of Znpt 2 and Cuptmentioning

confidence: 99%

Analysis, Fate and Toxicity of Zinc- and Copper Pyrithione in the Marine Environment

Dahllöf¹,

Grunnet²,

Haller³

et al. 2005

TemaNord

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“…The bactericide and fungicide agent 2-mercaptopyridine-N-oxide (PySH), or pyrithione, is widely used in cosmetic preparations and, in the form of its Zn(II) complex, which has marked antiseborrheic properties, in dermatological shampoos [1][2][3][4][5]. The use of such products contributes to the contamination of rivers, lakes and sea through urban wastewaters.…”

Section: Introductionmentioning

confidence: 99%

Electrooxidation of 2-Mercaptopyridine-N-oxide (Pyrithione) at Carbon Electrodes versus Mercury Electrodes

1998

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The electrooxidation of the bactericide and fungicide agent 2-mercaptopyridine-N-oxide (PySH), or pyrithione, was investigated by using mercury (Hg), glassy carbon (GCE), plastic formed carbon (PFCE) and paste (CPE) electrodes. From controlled-potential electrolyses or chronoamperometric measurements, the number of electrons involved in the oxidation processes was found to be close to unity in all cases. Voltammetric measurements showed that the irreversibility of the electron transfer must be related to the roughness and ordering in the surface of the electrode material: as the amorphous character of the carbon electrode was increased, the transfer appeared faster. Other effects as the O/C ratio or the removal of impurities can also influence the reversibility of the transfer. The rate constants of the electron transfers at zero potential were obtained. In addition, the extension of the adsorptive oxidation decreased when the amorphous character of the electrode was increased, but the Gibbs free enthalpy of this process did not vary from one electrode to another nor for the Hg electrode.

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Photodegradation of mercaptopyridine-N-oxide biocides

Cited by 30 publications

References 9 publications

Effects of metal pyrithione antifoulants on freshwater macrophyte Lemna gibba G3 determined by image analysis

Effects of metal pyrithione antifoulants on freshwater macrophyte Lemna gibba G3 determined by image analysis

Analysis, Fate and Toxicity of Zinc- and Copper Pyrithione in the Marine Environment

Electrooxidation of 2-Mercaptopyridine-N-oxide (Pyrithione) at Carbon Electrodes versus Mercury Electrodes

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