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Photochemical Fate of Organic Booster Biocides in the Aquatic Environment

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Antifouling Paint Biocides

Part of the book series: The Handbook of Environmental Chemistry ((HEC5,volume 5O))

Abstract

Considering the relevance and importance of photochemical processes in the environmental fate and behavior of organic micropollutants, the present review describes the state-of-the-art knowledge regarding the photodegradation of antifouling biocides in the aquatic environment. It includes data on photodegradation rates, primary and end photoproducts, and the pathways and mechanisms for most of the organic booster biocides (i.e., irgarol 1051, Sea-Nine 211, dichlofluanid, diuron, chlorothalonil, TCMTB, zinc and copper pyrithione, maneb, zineb, ziram, thiram, and triphenylboron-pyridine) used in antifouling paints.

Light-induced degradation took place both with direct or indirect (photosensitized) mechanisms via first-order kinetics. Direct photolysis in most cases seemed to be a minor event compared to photosensitized processes that usually enhanced the degradation. The composition of the water matrix is a key factor for the photofate of biocides in various natural waters. Half-lives ranged from a few minutes (zinc/copper pyrithiones) to several days (diuron and irgarol 1051) depending on the irradiation conditions as well as the constitution of the irradiated media. In most cases identified photoproducts were less toxic and innocuous than the parent compounds, however, the formation of more toxic compounds at the first degradation steps or synergistic effects among the transformation products should be taken into consideration.

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Abbreviations

3,4-DCA:

3,4-Dichloroaniline

APCI:

Atmospheric pressure chemical ionization

BT:

Benzothiazole

CDOM:

Colored dissolved organic matter

CPDU:

1-(3,4-Dichlorophenyl)-3,1-dimethylurea

CuPT:

Copper pyrithione

DCPMU:

1-(3,4-Dichlorophenyl)-3-methylurea

DCPU:

1-(3,4-Dichlorophenyl)urea

DMDC:

Dimethyldithiocarbamates

DMSA:

N,N-Dimethyl-N′-phenyl-sulfamide

DOM:

Dissolved organic matter

DTCs:

Dithiocarbamates

EBDC:

Ethylene(bis)dithiocarbamates

EBIS:

Ethylene(bis)isothiocyanate sulfide

EI-MS:

Electron impact–mass spectra

ETU:

Ethylenethiourea

EU:

Ethyleneurea

FA:

Fulvic acids

GC:

Gas chromatography

GS26575:

2-Methylthio-4-tert-butylamino-6-amino-s-triazine

HA:

Humic acids

IMO:

International Maritime Organization

LC:

Liquid chromatography

MBT:

2-Mercaptobenzothiazole

MBTS:

(bis)benzothiazolyl disulfide

MEPC:

Marine Environment Protection Committee

MS:

Mass spectrometry

MTBT:

2-(methylthio)benzothiazole

NHS:

Natural humic substances

NOS:

Natural occurring substances

OBT:

2(3H)-Benzothiazolone

OHBT:

2-hydroxybenzothiazole

PSA:

Pyridine-2-sulfonic-acid

SIM:

Selected ion monitoring

SPE:

Solid phase extraction

TBT:

Tri-butyl tin

TCMS pyridine:

2,3,5,6-Tetrachloro-4-(methyl sulphonyl) pyridine

TCMTB:

2-(thiocyanomethylthio)benzothiazole

TPBP:

Triphenylboron-pyridine

USEPA:

United States Environmental Protection Agency

UV:

Ultraviolet

ZnPT:

Zinc pyrithione

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Authors and Affiliations

  1. Chemistry Department, Laboratory of Industrial Chemistry, Ioannina University, 45110, Ioannina, Greece

    Vasilios A. Sakkas, Ioannis K. Konstantinou & Triantafyllos A. Albanis

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  1. Vasilios A. Sakkas
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  2. Ioannis K. Konstantinou
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  3. Triantafyllos A. Albanis
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Correspondence to Triantafyllos A. Albanis .

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Ioannis K. Konstantinou

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Sakkas, V.A., Konstantinou, I.K., Albanis, T.A. Photochemical Fate of Organic Booster Biocides in the Aquatic Environment. In: Konstantinou, I.K. (eds) Antifouling Paint Biocides. The Handbook of Environmental Chemistry, vol 5O. Springer, Berlin, Heidelberg . https://doi.org/10.1007/698_5_054

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