### A.I.Chemical Name: Zinc

- 2

- pyridinethiol

- 1

- oxide Copper

- 2

- pyridinethiol

- 1

- oxide

DP Barcode : D344371

Registrant: Arch Chemicals, Inc.

PC Code (s) : 088002 , 088001

Executive Summary (for Zn and Cu pyrithione)

Fate Assessment

Zinc Pyrithione (Zinc Omadine®) appears hydrolytically stable in abiotic, buffered and simulated water systems wit h an extrapolated half life between 99 and 123 days in buffered medium and 96 days (extrapolated) in simulated sea water (MRID

. 4 386 4602). However, Cu o madine hydrolysis is pH

- dependent with calculated half

- lives of 235, 107, and 9 days in pH 5, 7, and 9 buffers, respectively. Hydrolysis in seawater occurred with a half

- life of 16 days (MRID 45774322). B oth Zn and Cu omadine degrade rapidly in both fresh and salt irradiated water with half

- lives of 11

- 36 minutes (MRIDs 44011501, 45774323). In a literatu re study, b oth Zn and Cu omadine hydrolyzed rapidly in seawater with half

- lives of 8.3 and 7.1 minutes, respectively (Maraldo and Dahllof

, 2004). Nitrate and dissolved organic matter increase this degradation rate (Sakkas et al., 2007). These data indic ate that in shallow, well

- mixed, and clear irradiated waters, Zn and Cu omadine will degrade rapidly. However, suspended sediment and shading will inhibit this route of degradation.

There are multiple microbial degradat ion pathways for Zn and Cu omadin e in aquatic systems

. Both compounds degrade rapidly in anaerobic aqu a tic studies (representing bottom sediment) with half

- lives of 31

- 75 minutes (MRIDs 44010403, 44850002, 44850001). However, the two compounds differed in the degradation rate under aero bic aquatic conditions (representing surface water). The half

- lives were 35

- 59 minutes for Zn omadine (MRIDs 44850004 and 45876501) and 4.7 hours for Cu omadine (MRID 44850003). In many studies, Zn omadine was observed to transchelate to Cu omadine which was more stable.

Zinc omadine shows a moderately strong tendency to bind with soils and sediments: With salt water soil and sediment , the K d 

### s are 50 and 99 ml/g, respectively. Tendency to bind with freshwater soils and sediments are less strong and obs erved K d 

### s are 11 and 48 ml/g

, respectively (MRID 440010402). Z inc omadine is not likely to bio concentrate in aquatic organisms based on the bioconcentration factor of <1 (MRID 45201401). Copper omadine has a similar sorption potential to soil with a Kd v alue of 38.7 and a Koc value of 5528 ml/g.

### Leaching of Zn and Cu omadine does occur from treated paint. For Zn omadine,

t he maximum, minimum, and average leaching rates were 7.3

- 14.3

, 0.95

- 5.9 , and 1 .3

- 7.4 ug/cm 2 

### /day, respectively. For Cu omadine, th e maximum, minimum, and average leaching rates were 5.0

- 9.3, 2. 9

- 4.6, and 3.9

- 6 ug/cm 2 

### /day, respectively.

In the UK, Zn pyrithione was not found (<20 ng/l) in seawater. However, it is known to undergo transchelation with copper and possibly manganese replacing the zinc ion (Konstantinou and Albanis, 2004). The registrant acknowledges this transchelation in several studies.

Even though Zn and Cu omadine are relatively non

- persistent, chronic exposure is likely to occur due to trannschelation and co ntinuous exposure in aquatic environments. In a harbor, boats will reside continuously and the antifoulants in the paint will leach while they sit. Also, larger boats and ships will arrive periodically and bring more exposure. The primary exposure to t hese compounds is the non

- chelated omadine and pyridine degradates with different levels of reduction and oxidation that are formed at

> 10 % of applied parent compound. They include:

Omadine disulfide Omadine sulfinic acid Omadine sulfonic acid Omadine thiosulfonic acid Pyridine disulfide Pyridine sulfinic acid Pyridine sulfonic acid 2

- mercaptopyridine / 2

- mercaptopyrine

- N

- oxide (mixed disulfides)

Tables 1 and 2 contain the environmental fa te data for Zn omadine, and Table 3 contains the data for Cu omadi ne. The percentages of each degradate may be seen for each individual study in Tables 1 and 3.

Bridging from Zinc to Copper Omadine

Bridging from Zinc to Copper Omadine

The registrant for zinc omadine is requesting a registration for copper omadine b ased on the zinc omadine data. They are requesting that the Antimicrobial Division bridge the Zn omadine data to satisfy the data requirements for Cu omadine. They have several proposed justifications for this proposal, including similarity of results in guideline tests and different association constants . The registrant used chemical equilibria of Pt complexes with Cu(II), Zn(II), Fe(III), Ni(II), Co(II), and Mn(II) to illustrate competitive equilibria with the Pt ligand. They did not address the stabi lity of the Cu(I)

- Pt or Fe(II)

- Pt ligand complexes. It is important to note that the activities of Cu(I) and Fe(II) will increase in anaerobic (anoxic) environments (Lindsay, 1979). The stability diagrams of metal

- Pt complexes show that the Cu(II)

- Pt comp lex is the predominant metal complex at Cu(II) concentrations ranging from 0.001 to 10 ug/L.

### Therefore, the Cu(II)

- Pt, based on chemical equilibria, is expected to be the

predominant Pt

- metal complex in aerobic (oxic) aquatic environments and bridging is appropriate.

The registrant correctly noted that the guideline environmental fate data that incorporates both Zn and Cu omadine provide consistent results (See Table 4). The aquatic metabolism data show short half

- lives in total water:sediment systems with consistent degradates that are formed for both chemicals, and sorption is similar for both.

According to the registrant, the association constants are much higher for copper omadine than for any other chelation product (MRID 45774327). A higher association constant indicates higher stability of the chelate. The association constant for Cu is >8.5 compared to 5.3 for Zn. However, they acknowledged that other ions (e.g. Fe, Mn) will be in equilibrium with Zn and Cu and will form omadine ch elates as well. To justify their argument, the registrant provided association constants and a mole fraction diagram for Cu (II/I), Zn, Fe (II/III), Mn, Ca, Mg, and H as a function of pH. The submitted Excel spreadsheet and PowerPoint presentation clearl y demonstrate this phenomenon. In descending order, the maximum predicted chelation was for Cu(II), followed by Fe(III), Zn(II), Ni(II), Co(II), Mn(II), Mg(II) and Ca(II).

### Table 1. Summary of Results from Environmental Degradation and

Bioconcentrati on Data for Zinc Omadine

Guideline Half

- life(s) Major degradates Percentages References

Hydrolysis (161

- 1) pH 5 (freshwater) 99 days Omadine disulfide Max of 21 % by end of study (30 days) 43864602

pH 7 (freshwater) 120 days Omadine disulfide Max of 16 % by end of study (30 days) pH 9 (freshwater) 123 days Omadine sulfinic acid Max of 12 % by end of study (30 days) Seawater (pH 8.2) 96 days Omadine sulfinic acid Max of 17 % by end of study (30 days) Photodegradation in Water (161

- 2) pH 9 (fre shwater) 11 minutes Pyridine disulfide Max of 11.2

- 11.7 % by 1 hour, and non

- detectable by 1

- 14 days 44011501

Pyridine sulfonic acid Max of 70

- 71 % by end of study (30 days) Mixed disulfides (2

- mercaptopyridine and 2

- mercaptopyridine

- N

- oxide Max o f 11 % by 15 minutes, <10 % otherwise Seawater (pH 8.2) 14 minutes Pyridine disulfide Max of 12.5 % by 1 hour, and non

- detectable by 1 day Pyridine sulfonic acid Max of 70

- 74 % by end of study (30 days) Anaerobic Aquatic Metabolism (representing b ottom sediment)

— 162

- 3 Freshwater system 75 minutes Omadine sulfinic acid Max of 13 % by 6 hours, and average of 5 % until end of study (91 days) 44010403

Omadine disulfide Max of 26 % by 3 days, and near non

- detectable by 30 days Pyridine sulfinic acid Max of 32 % by end of study (91 days) Pyridine sulfonic acid Max of 23 % by 18 hours, and 0.46 % by 91 days Mixed disulfides Max of 7

- 15 % by 2

- 91 days Pyridine disulfide Max of 11 % by 14

- 91 days (end of study) Saltwater system 57 min utes Omadine disulfide Max of 31 % at day zero,

non

- detectable by 30 days Pyridine sulfinic acid Max of 57 % by 90 days (end of study) Pyridine sulfonic acid Max of 11 % by 7 days, 2.5 % by 90 days Pyridine disulfide Max of 11

- 12 % by 2

- 3 d ays, 0.03 % by 90 days Saltwater 31 minutes Omadine sulfinic acid Max of 11

- 14 % at zero 44850002system days, minor concentrations after 2

- mercaptopyridine Max of 71

- 78 % by 7 days, 33

- 34 % by 30 days (end of study) Aerobic Aquatic Metabolism (re presenting surface water)

— 162

- 4 Saltwater system 59 minutes Omadine sulfinic acid Max of 36

- 46 % by 3

- 7 days, 7

- 18 % by 30 days (end of study) 44850004

Omadine sulfonic acid Max of 22

- 35 % by 30 days Omadine thiosulfonic acid Max of 21

- 26 % by 0 days, 7

- 8 % by 30 days Pyridine sulfonic acid Max of 12

- 15 % by 30 days Outdoor microcosm test (Aerobic Aquatic Metabolism with light)

— 164

- 2 Saltwater system 35 minutes Omadine sulfonic acid Max of 18 % by 1 hour, not detected by 8 hours 4587650 1

Omadine sulfinic acid Max of 19 % by 4 hours,

non

- detectable by 30 days Pyridine sulfinic acid Max of 29 % by 1 day,

non

- detectable by 14 days Pyridine sulfonic acid Max of 82 % by 14 days, 76 % by 30 days Bioaccumulation in non

- target aq uatic organisms (165

- 5) Bioconcentration was negligible with bioconcentration factors of <1. MRID 45201401

Leaching from Green Paint Maximum average leach rate (ug/cm 2 /day) 9.0 (day 1) MRID 47171304 40.43 % CuO and 3 % Zn Omadine Minimum average lea ch rate (ug/cm 2 /day) 1.6 (day 45)

Cumulative leach rate (ug/cm 2 ) 111 (days 0

- 45)

Mean leach rate (ug/cm 2 /day) 2.5 (days 0

- 45) Leaching from Red Paint Maximum average leach rate (ug/cm 2 /day) 7.8 (day 21) MRID 47171305 40.43 % CuO and 3 % Zn Omadine Minimum average leach rate (ug/cm 2 /day) 1.4 (day 45)

Cumulative leach rate (ug/cm 2 ) 103 (days 0

- 45)

Mean leach rate (ug/cm 2 /day) 2.3 (days 0

- 45)

Leaching from BluePaint Maximum average leach rate (ug/cm 2 /day) 7.3 (day 1) MRID 47171303 40.43 % CuO and 3 % Zn Omadine Minimum average leach rate (ug/cm 2 /day) 1.5 (day 42)

Cumulative leach rate (ug/cm 2 ) 114 (days 0

- 45)

Mean leach rate (ug/cm 2 /day) 2.5 (days 0

- 45) Leaching from Black PaintMaximum average leach rate

(ug/cm 2 /day) 8.8 (day 1) MRID 47188401 40.43 % CuO and 3 % Zn Omadine Minimum average leach rate (ug/cm 2 /day) 1.4 (days 21

- 45)

Cumulative leach rate (ug/cm 2 ) 105 (days 1

- 45)

Mean leach rate (ug/cm 2 /day) 2.3 (days 1

- 45) Leaching from Alumaspray+ 1863 Black Paint Maximum averag e leach rate (ug/cm 2 /day) 8.02 (day 24) MRID 46547404 1.43 % Zn Omadine Minimum average leach rate (ug/cm 2 /day) 1.3 (day 45)

Cumulative leach rate (ug/cm 2 ) 183 (days 1

- 45)

Mean leach rate (ug/cm 2 /day) 4.1 (days 1

- 45) Leaching from Alumaspray+ 1763 Gray Paint Maximum average leach rate (ug/cm 2 /day) 9.1 (day 1) MRID 46547403 1.43 % Zn Omadine Minimum average leach rate (ug/cm 2 /day) 1.5 (day 45)

Cumulative leach rate (ug/cm 2 ) 136 (days 1

- 45)

Mean leach rate (ug/cm 2 /day) 3.0 (days 1

- 45) Leachin g from Alumaspray+ 1262 Blue Paint Maximum average leach rate (ug/cm 2 /day) 7.6 (day 10) MRID 46632004 4.95 % Zn Omadine Minimum average leach rate (ug/cm 2 /day) 2.8 (day 45)

Cumulative leach rate (ug/cm 2 ) 228 (days 1

- 45)

Mean leach rate (ug/cm 2 /day) 5.1 (days 1

- 45)

Leaching from International Copper

- Free, White Paint Maximum average leach rate (ug/cm 2 /day) 14.3 (day 1) MRID 47039201 4.34 % Zn Omadine Minimum average leach rate (ug/cm 2 /day) 4.3 (day 45)

Cumulative leach rate (ug/cm 2 ) 322 (days 1

- 45)

Mean leach rate (ug/cm 2 /day) 7.2 (days 1

- 45) Leaching from Ecoflex BEA368/G584 Paint Maximum average leach rate (ug/cm 2 /day) 13 (day 7) MRID 44877103 Zn omadine percentage not available Minimum average leach rate (ug/cm 2 /day) 5.9 (day 49)

Cum ulative leach rate (ug/cm 2 ) 423 (days 1

- 49)

Mean leach rate (ug/cm 2 /day) 8.6 (days 1

- 49) Leaching from Ecoflex BEA369/G044 Paint Maximum average leach rate (ug/cm 2 /day) 13 (day 1) MRID 44877104 Zn omadine percentage not available Minimum average leac h rate (ug/cm 2 /day) 5.1 (day 49)

Cumulative leach rate (ug/cm 2 ) 361 (days 1

- 49)Mean leach rate (ug/cm 2 /day) 7.4 (days 1

- 49) Leaching from Ecoflex BEA468/G580 Paint Maximum average leach rate (ug/cm 2 /day) 11 (day 3) MRID 44877104 Zn omadine percent age not available Minimum average leach rate (ug/cm 2 /day) 3.9 (day 49)

Cumulative leach rate (ug/cm 2 ) 298 (days 1

- 49)

Mean leach rate (ug/cm 2 /day) 6.1 (days 1

- 49) Leaching from Ecoflex BEA469/G044 Paint Maximum average leach rate (ug/cm 2 /day) 7.1 (day 7) MRID 44877106 Zn omadine percentage not available Minimum average leach rate (ug/cm 2 /day) 3.2 (day 49)

Cumulative leach rate (ug/cm 2 ) 242 (days 1

- 49)

Mean leach rate (ug/cm 2 /day) 4.9 (days 1

- 49) Leaching from Ecoflex BEA469/G044 Paint Maxi mum average leach rate (ug/cm 2 /day) 4.5 (day 1) MRID 44833310 4.7 % Zn omadine Minimum average leach rate (ug/cm 2 /day) 0.95 (day 38)

Cumulative leach rate (ug/cm 2 ) 64.6 (days 1

- 49)

Mean leach rate (ug/cm 2 /day) 1.3 (days 1

- 49)


### Table 2. Leaching

- Ad sorption

- Desorption Data for Zn Omadine (MRID 44010402)

Soil/Sediment Kads

(ml/g) Koc

(ml/g) Kdes

(ml/g) Koc

(ml/g) Comment(s)

Marblehead salt soil 50 2,347 71 3,293 Sorption unrelated to clay, organic matter, or pH Sorption coefficients are for mixture of compounds Portland fresh soil 11 784 13 873

Marblehead salt sediment 99 10,633 202 21,814

Portland fresh sediment 48 3,597 87 6,524Ta ble 3. Summary of Results from Environmental Degradation Data for Copper Omadine

Guideline Half

- life(s) Maj or

degradates Percentages References

Hydrolysis (161

- 1) pH 5 (freshwater) 235 days None Not applicable 45774322 pH 7 (freshwater) 107 days Omadine sulfinic acid Max of 13 % by

30 days (end of study) pH 9 (freshwater) 9.1 days Omadine disulfide Max of 10 % by 7 days, 0.6 % by 30 days Omadine sulfinic acid Max of 69 % by

30 days Seawater (pH 8.2) 16 days Omadine sulfinic acid Max of 57

- 61 %

by 21

- 30 days Photodegradation in Water (161

- 2) pH 5 (freshwater) 36 minutes Lactam Max of 29 % by 17 da ys (end of study) 45774323

Pyridine sulfinic acid Max of 43 % by 6

hours, 2 % by 17 days Pyridine sulfonic acid Max of 42 % by

17 days Seawater (pH 8.2) 31 minutes Lactam (reaction intermediate) Max of 64 % by

17 days (end of study) Pyridine s ulfinic acid Max of 38 % by 6

hours, non

detectable by 17 days Pyridine sulfonic acid Max of 36 % by

7

- 17 days Anaerobic Aquatic Metabolism (162

- 3) Saltwater system 34 minutes 2

- mercaptopyridine Max of 78 % by 7

days, 2.3 % by 182 days (end of study ) 44850001

Omadine sulfinic acid Max of 13.8 % at

time 0, non

detectable by 14 days Aerobic Aquatic Metabolism (162

- 4) Freshwater system 4.7 hours Omadine sulfinic acid Max of 42 % by 7

days, 1.7 % by 84 days (end of study) 44850003

Omadine sulfon ic acid Max of 29

- 35 %

by 21

- 84 days Omadine thiosulfonic acid Max of 41 % by 1

day, 4.4 % by 84 days Pyridine sulfonic acid (M

- 7) Max of 25 % by

84 days.Leaching from Brown Paint

Maximum average leach rate (ug/cm 2 /day) 6.5 (day 45) MRID 47107 710 , 46105309 Minimum average leach rate (ug/cm 2 /day) 4.6 (day 14)

Cumulative leach rate (ug/cm 2 ) 240 (days 1

- 45) Mean leach rate (ug/cm 2 /day) 5.33 (days 1

- 45) Leaching from Dark Red Paint Maximum average leach rate (ug/cm 2 /day) 9.3 (day 3) MRID 47107709 , 46105308 Minimum average leach rate (ug/cm 2 /day) 4 .1 (day 28)

Cumulative leach rate (ug/cm 2 ) 270 (days 1

- 45) Mean leach rate (ug/cm 2 /day) 6.0 (days 1

- 45) Leaching from Dark Red Paint Maximum average leach rate (ug/cm 2 /day) 5.0 (day 7) MRID 45793501 Minimum average leach rate (ug/cm 2 /day) 2.9 (day 38)

Cumulative leach rate (ug/cm 2 ) 161 (days 1

- 45) Mean leach rate (ug/cm 2 /day) 3.9 (days 1

- 45) Soil Leaching

- Adsorption

- Desorption Kd (ml/g) 38.7 MRID 45780508 Koc (ml/g) 5528

### Table 4. Comparison of Environmental Fate Results for Copper Omadine and Zinc

Omadine

Zinc Omadine Copper Omadine Test Guideline Half

- life Degradates Test Guideline Half

- life Degradates Hydrolysis (835.2120, 161

- 1, MRID 43864602) Hydrolysis (835.2120, 161

- 1, MRID 45774322) pH 5 (freshwater) 99 days Omadine disulfide pH 5 (freshwater) 235 days None

pH 7 (freshwater) 120 days Omadine disulfide pH 7 (freshwater) 107 days Omadine sulfinic acid pH 9 (freshwater) 123 days Omadine sulfinic acid pH 9

(freshw ater) 9.1 days Omadine disulfide Omadine sulfinic acid Seawater (pH 8.2) 96 days Omadine sulfinic acid Seawater (pH

8.2) 16 days Omadine sulfinic acid Photodegradation in Water (835.2240, 161

- 2,

MRID 44011501) Photodegradation in Water (835.2240, 161

- 2, MRID 45774323) pH 9 (freshwater) 11 minutes Pyridine disulfide Pyridine sulfonic acid Mixed disulfides (2

- mercaptopyridine and 2

- mercaptopyridine

N

- oxide) pH 5

(freshwater) 36 minutes Lactam Pyridine sulfinic acid Pyridine sulfonic acid

pH 8.2 (Seawa ter) 14 minutes Pyridine disulfide Pyridine sulfonic acid pH 8.2

(seawater) 31 minutes Lactam Pyridine sulfinic acid Pyridine sulfonic acid Anaerobic Aquatic Metabolism (835.4300, 162

- 3,

MRID 44010403, 44850002) Anaerobic Aquatic Metabolism (835.4300, 1 62

- 3, MRID 44850001) Freshwater system 75 minutes Omadine sulfinic acid Omadine disulfide Pyridine sulfinic acid Pyridine sulfonic acid Mixed disulfides Pyri di ne disulfide No data

Saltwater system 57 minutes Omadine disulfide Pyridine sulfinc acid Pyridi ne sulfonic acid Pyridine disulfide Saltwater system 31 minutes 2

- mercaptopyridine Omadine sulfinic acid

Saltwater system 31 minutes Omadine sulfinic acid 2

- mercaptopyridine (one of the mixed disulfides)Aerobic Aquatic Metabolism (835.4400, 162

- 4/164

- 4, MRID 44850004, 45876501 Aerobic Aquatic Metabolism (835.4400, 162

- 4, MRID 4850003) Saltwater system 59 minutes Omadine sulfinic acid Omadine sulfonic acid Omadine thiosulfonic acid Pyridine sulfonic acid Freshwater

system 5 hours Omadine sulfinic aci d Omadine sulfonic acid Omadine thiosulfonic acid Pyridine sulfonic acid Saltwater system (Outdoor microcosm with light) 35 minutes Omadine sulfinic acid Omadine sulfonic acid Pyridine sulfinic acid Pyridine sulfonic acid No data

Leaching and Adsorption Desorption (835.1230,

163

- 1, MRID 44010402) Leaching and Adsorption Desorption (835.1230, 163

- 1, MRID 45780508) Kad (Kads values ) ml/g 11

- 99 (soils

and sediments) For mixture of compounds Not applicable 38 Not applicable Not applicable

Bioconcentratio n in non

- target organisms (850.1710, 165

- 5, MRID 45201401) Bioconcentration in non

- target organisms (165

- 5) Bioconcentration was negligible with bioconcentration factors of <1. Not

applicable Not applicable No data (no bioconcentration expected) Not

app licable Not applicable

Leaching rates from treated paints (ASTM 5108

- 90, MRIDs 47171304, 47071305, 47171303, 47188401, 46547404, 46547403, 46632004, 47039201, 44877103, 44877104, 44877105,

448771016, 44833310) Leaching rates from treated paints (ASTM D5 108

- 90, MRIDs 47107710, 46105309, 47107709, 45793501)

Maximum leaching rates (ug/cm 2 /day) 4.5

- 14

(average of 9.3) Not applicable Maximum leaching rates (ug/cm 2 /day) 5

- 9.3

(average of 6.9) Not applicable

Minimum average leach rate (ug/cm 2 /day) 0.95

- 5. 9

(average of 2.7) Minimum average leach
rate (ug/cm 2 /day) 2.9

- 4.6

(average of 3.9)

Cumulative each rate (ug/cm 2) 65

- 423

(average of 207) Cumulative each rate (ug/cm 2) 161

- 270

(average of 224) Mean leach rate (ug/cm 2 ) 1.3

- 7.4

(average of 4.4) M ean leach rate (ug/cm 2 ) 3.9

- 6

(average of 4.4)

### References

Open Literature references

Konstantinou, I.K and T.A. Albanis. 2004. Worldwide occurrence and effects of antifouling paint booster biocides in the aquatic environment: a review. Environment International 30(2004): 235

- 248.

Lindsay, Willard L. 1979. Chemical Equilibria in Soil. Wiley Interscience, John Wiley and Sons, New York.

Maraldo, K. and L. Dahliof. 2004. Seasonal variations in the effect of zine pyrithione and copper pyrithione on pelagic phytoplankton communities. Aquatic toxicology (2004)): 189

- 198.

Sakkas, V.A, K. Shibata, Y. Yamaguchi, S. Sugasawa, and T. Albanis. 2007. Aqueous phototransformation of zinc pyrithione. Degradation kinetics and by

- product identification by liquid chromatography

- atmospheric pressure chemical ionization mass spectrometry. Journal of Chromatography A, 1144 (2007) 175

- 182.

### Submitted Guideline Studies



## Zinc Omadine

161

- 1 Hydrolysis

MRID Citation Reference

43864602 Reynolds, J. (1995 ) Hydrolysis of (Pyridine

- 2,6

- (carbon 14)) Zinc Omadine: Lab

Project Number: XBL 94052: RPT00217: 94052. Unpublished study prepared by XenoBiotic Labs, Inc. 128 p.



## 835.2130 Hydrolysis as a function of pH and temperature

MRID Citation Reference

46101101 Turley, P. (2003) Calculation of Predicted Environmental Concentrations of Zinc

Pyrithione in Antifouling Applications. Project Number: CASR/04/2003. Unpublished study prepared by Biocides Technology. 74 p.



## 161

- 2 Photodegradation

- water

MR ID Citation Reference

43864601 Reynolds, J. (1995) Aqueous Photolysis of (Pyridine

- 2,6

- (carbon 14)) Zinc

Omadine in pH 9 Buffer and Artificial Sea Water: Lab Project Number: 95025: RPT00243: XBL 95025. Unpublished study prepared by XenoBiotic Labs, I nc. 130 p.

44011501 Reynolds, J. (1996) Aqueous Photolysis of (pyridine

- 2,6

- (carbon 14))Zinc

Omadine in pH 9 Buffer and Artificial Seawater: Revised Report: Lab Project Number: 95025: RPT00243: XBL 95025. Unpublished study prepared by XenoBiotic Labs, In c. 139 p.

45876501 McLaughlin, S. (2003) Zinc Pyrithione Outdoor Microcosm Study: Lab Project

Number: 13778.6100: 082001. Unpublished study prepared by Springborn Smithers Laboratories. 141 p. {OPPTS 835.3180, 835.0001}



## 835.2210 Direct photolysis rate in water by sunlight

MRID Citation Reference

46101101 Turley, P. (2003) Calculation of Predicted Environmental Concentrations of Zinc

Pyrithione in Antifouling Applications. Project Number: CASR/04/2003. Unpublished study prepared by Biocides T echnology. 74 p.

## 162

- 3 Anaerobic aquatic metab.

MRID Citation Reference

44010403 Smalley, J.; Reynolds, J. (1996) Anaerobic Aquatic Metabolism of (Pyridine

2,6

- (carbon 14)) Zinc Omadine in Fresh Water and Sea Water: Lab Project Number: 95022: RPT00241. Unpublished study prepared by XenoBiotic Labs., Inc. 232 p.

44509701 Ritter, J. (1998) Summary of the Aerobic and Anaerobic Aquatic Metabolism of

(pyridine

- 2,6

- (carbon 14)) Copper Omadine and (pyridine

- 2,6

- (carbon 14)) Zinc Omadine in Marine Wa ter and Sediment: (Interim Report): Lab Project Number: 42

- 96B10CUOM: 45

- 97B10ZNOM: 49

- 97B10ZPT. Unpublished study prepared by Olin Research Center. 16 p.

44850001 Ritter, J. (1999) Anaerobic Aquatic Metabolism of (pyridine

- 2,6

- (carbon

- 14))

Copper Omadin e in Marine Water and Sediment: Lab Project Number: 50

- 97B10CUOM. Unpublished study prepared by Arch Chemicals, Inc. 201 p.

44850002 Ritter, J. (1999) Supplemental Anaerobic Aquatic Metabolism of (pyridine

- 2,6

-

(carbon

- 14)) Zinc Omadine in Marine Water an d Sediment: Lab Project Number: 49

- 97B10ZPT. Unpublished study prepared by Arch Chemicals, Inc. 126 p.

46101101 Turley, P. (2003) Calculation of Predicted Environmental Concentrations of Zinc

Pyrithione in Antifouling Applications. Project Number: CASR/0 4/2003. Unpublished study prepared by Biocides Technology. 74 p.



## 162

- 4 Aerobic aquatic metab.

MRID Citation Reference

44010401 Ritter, J. (1996) Aerobic Aquatic Metabolism of (Pyridine

- 2,6

- (carbon 14)) Zinc

Omadine: (Final Report): Lab Project Number: 29

- 95B10ZPT. Unpublished study prepared by Olin Research Center. 292 p.

44509701 Ritter, J. (1998) Summary of the Aerobic and Anaerobic Aquatic Metabolism of

(pyridine

- 2,6

- (carbon 14)) Copper Omadine and (pyridine

- 2,6

- (carbon 14)) Zinc Omadine i n Marine Water and Sediment: (Interim Report): Lab Project Number: 42

- 96B10CUOM: 45

- 97B10ZNOM: 49

- 97B10ZPT. Unpublished study prepared by Olin Research Center. 16 p.

44850003 Ritter, J. (1999) Aerobic Aquatic Metabolism of (pyridine

- 2,6

- (carbon

- 14))

Copp er Omadine in Marine Water and Sediment: Lab Project Number: 42

- 96B10CUOM. Unpublished study prepared by Arch Chemicals, Inc. 168 p.

44850004 Ritter, J. (1999) Supplemental Aerobic Aquatic Metabolism of (pyridine

- 2,6

-

(carbon

- 14)) Zinc Omadine in Marine W ater and Sediment: Lab Project Number: 45

- 97B10ZNOM. Unpublished study prepared by Arch Chemicals, Inc. 143 p.

46101101 Turley, P. (2003) Calculation of Predicted Environmental Concentrations of Zinc

Pyrithione in Antifouling Applications. Project Number : CASR/04/2003. Unpublished study prepared by Biocides Technology. 74 p.

## 163

- 1 Leach/adsorp/desorption

MRID Citation Reference

44010402 Wisocky, M.; Reynolds, J. (1996) Adsorption and Desorption of (pyridine

- 2,6

-

(carbon 14)) Zinc Omadine in Tw o Sediments and Two Terrestrial Soils: Revised: Lab Project Number: 95023: RPT00242. Unpublished study prepared by XenoBiotic Labs., Inc. 195 p.

45565201 Ritter, J. (2001) Zinc Pyrithione Soil Column Leaching Study: Lab Project

Number: 72

- 00B10ZPT. Unpub lished study prepared by Arch Chemicals, Inc. 179 p.

47695602 Chang, S. (2009) Measurement of Zinc Pyrithone Leached from Polyester

Fabrics. Project Number: CASR/01/2009. Unpublished study prepared by Arch Chemicals, Inc. 30 p.



## 164

- 2 Aquatic field dissipation

MRID Citation Reference

45876501 McLaughlin, S. (2003) Zinc Pyrithione Outdoor Microcosm Study: Lab Project

Number: 13778.6100: 082001. Unpublished study prepared by Springborn Smithers Laboratories. 141 p. {OPPTS 835.3180, 835.0001}



## 1 65

- 5 Bioaccum

- aquatic non

- target

MRID Citation Reference

45204101 Ward, T.; Boeri, R. (2000) Bioconcentration Test with Zinc (pyridine

- 2,6

- (14)C)

Omadine and the Oyster, Crassostrea virginica. Unpublished study prepared by T.R. Wilbury Laborato ries, Inc. 54 p.



## ASTM D5108

- 90 Leaching from Treated Paint

44587209 Ritter, J. (1998) Zinc Omadine Leach Rates from Four Ecoloflex Paints in

Synthetic Seawater: Lab Project Number: 54

- 97B10ZPT: 57

- 97B10ZPT: 58

- 98B10ZPT. Unpublished study prepared by Olin Biocides. 23 p.

44833310 Audette, D. (1998) Leach Rate of Zinc and Zinc Omadine from Two E. Paint

Antifouling Paints: Lab Project Number: 47

- 97B10ZPT: ASTM D5108

- 90. Unpublished study prepared by Olin Research Center. 92 p.

44877103 Ritter, J. (19 99) Leach Rate of Zinc Omadine from Ecoloflex BEA368/G584

Paint in Synthetic Seawater: Lab Project Number: 54

- 97B10ZPT. Unpublished study prepared by Arch Chemicals, Inc. 58 p.

### 44877104 Ritter, J. (1999) Leach Rate of Zinc Omadine from Ecoloflex BEA369 /G044 Paint in Synthetic Seawater: Lab Project Number: 57

- 98B10ZPT. Unpublished study prepared by Arch Chemicals, Inc. 58 p.

44877105 Ritter, J. (1999) Leach Rate of Zinc Omadine from Ecoloflex BEA468/G580

Paint in Synthetic Seawater: Lab Project Number: 58

- 98B10ZPT. Unpublished study prepared by Arch Chemicals, Inc. 58 p.

44877106 Ritter, J. (1999) Leach Rate of Zinc Omadine from Ecoloflex BEA469/G043

Paint in Synthetic Seawater: Lab Project Number: 59

- 98B10ZPT. Unpublished study prepared by Arch Chemi cals, Inc. 58 p.

44974202 Boeri, R.; Rondon, C.; Ward, T. (1999) Leach Rate of Zinc Omadine from

Micron Optima Paint in Synthetic Seawater: Lab Project Number: 1706

- OL. Unpublished study prepared by T.R. Wilbury Labs., Inc. 52 p.

45347201 Boeri, R.; Ro ndon, C.; Ward, T. (2000) Leach Rate of Zinc Omadine from

Micron Optima Red in Synthetic Seawater: Lab Project Number: 1980

- IP. Unpublished study prepared by T.R. Wilbury Laboratories, Inc. 50 p.

45347202 Boeri, R.; Rondon, C.; Ward, T. (2000) Leach Rate of Zinc Omadine from

Micron Optima Black in Synthetic Seawater: Lab Project Number: 1981

- IP. Unpublished study prepared by T.R. Wilbury Laboratories, Inc. 50 p.

45349801 Boeri, R.; Rondon, C.; Ward, T. (2000) Leach Rate of Zinc Omadine from

Intersmooth 360 Ecoloflex BEA 363 Dark Brown in Synthetic Seawater: Lab Project Number: 1976

- IP. Unpublished study prepared by T.R. Wilbury Labs., Inc. 51 p.

45349802 Boeri, R.; Rondon, C.; Ward, T. (2000) Leach Rate of Zinc Omadine from

Intersmooth 360 Ecoloflex BE A 364 Dark Red in Synthetic Seawater: Lab Project Number: 1977

- IP. Unpublished study prepared by T.R. Wilbury Labs., Inc. 50 p.

45349803 Boeri, R.; Rondon, C.; Ward, T. (2000) Leach Rate of Zinc Omadine from

Intersmooth 460 Ecoloflex BEA 463 Dark Brown i n Synthetic Seawater: Lab Project Number: 1978

- IP. Unpublished study prepared by T.R. Wilbury Labs., Inc. 50 p.

45349804 Boeri, R.; Rondon, C.; Ward, T. (2000) Leach Rate of Zinc Omadine from

Intersmooth 460 Ecoloflex BEA 464 Dark Red in Synthetic Seawat er: Lab Project Number: 1979

- IP. Unpublished study prepared by T.R. Wilbury Labs., Inc. 50 p.

45690201 Boeri, R.; Rondon, C.; Ward, T. (2002) Leach Rate of Zinc Omadine from

Multi

- Micron Antifouling

-- Blue in Synthetic Seawater: Lab Project Number: 2348

- IP . Unpublished study prepared by T.R. Wilbury Laboratories, Inc. 44
p.

### 45690202 Boeri, R.; Rondon, C.; Ward, T. (2002) Leach Rate of Zinc Omadine from Multi

- Micron Antifouling

-- Red in Synthetic Seawater: Lab Project Number: 2349

- IP. Unpublished study prepared by T.R. Wilbury Laboratories, Inc. 44
p.
45690203 Boeri, R.; Rondon, C.; Ward, T. (2002) Leach Rate of Zinc Omadine from

Multi

- Micron Antifouling

-- Black in Synthetic Seawater: Lab Project Number: 2350

- IP. Unpublished study prepared by T.R. Wilbu ry Laboratories, Inc. 44
p.
45811901 Boeri, R.; Rondon, C.; Ward, T. (2002) Leach Rate of Zinc Omadine from

Superyacht 800 Antifouling

-- White in Synthetic Seawater: Lab Project Number: 2369

- IP. Unpublished study prepared by T.R. Wilbury Laboratories, Inc . 44 p.

45811902 Boeri, R.; Rondon, C.; Ward, T. (2002) Leach Rate of Zinc Omadine from

Superyacht 800 Antifouling

-- Red in Synthetic Seawater: Lab Project Number: 2371

- IP. Unpublished study prepared by T.R. Wilbury Laboratories, Inc. 44 p.

45811903 Boe ri, R.; Rondon, C.; Ward, T. (2002) Leach Rate of Zinc Omadine from

Superyacht 800 Antifouling

-- Blue in Synthetic Seawater: Lab Project Number: 2370

- IP. Unpublished study prepared by T.R. Wilbury Laboratories, Inc. 44 p.

45811904 Boeri, R.; Rondon, C.; W ard, T. (2002) Leach Rate of Zinc Omadine from

Superyacht 800 Antifouling

-- Black in Synthetic Seawater: Lab Project Number: 2372

- IP. Unpublished study prepared by T.R. Wilbury Laboratories, Inc. 44 p.

46059703 Sinning, D. (2002) Leach Rate Determination of Pettit Marine Paint

Alumacoat SR Antifouling Paint 1261 Blue Containing Zinc Omadine. Project Number: 390/59. Unpublished study prepared by Case Consulting Laboratories, Inc. 22 p.

46059704 Sinning, D. (2002) Leach Rate Determination of Pettit Marine P aint

Alumacoat SR Antifouling Paint 1861 Black Containing Zinc Omadinet. Project Number: 390/60. Unpublished study prepared by Case Consulting Laboratories, Inc. 22 p.

46059705 Sinning, D. (2002) Leach Rate Determination of Pettit Marine Paint

Alumacoat S R Antifouling Paint 1161 White Containing Zinc Omadine. Project Number: 390/62. Unpublished study prepared by Case Consulting Laboratories, Inc. 22 p.

46059706 Sinning, D. (2002) Leach Rate Determination of Pettit Marine Paint

Alumacoat SR Antifouling Pai nt 1661 Red Containing Zinc Omadine. Project Number: 390/63. Unpublished study prepared by Case Consulting Laboratories, Inc. 22 p.

### 46088608 Sinning, D. (2003) Leach Rate Determination of Sea Nine TM21 1 Antifouling Agent and Zinc Omadine from Sea Grand P rix CF

- 10: Final Report. Project Number: 2750/03. Unpublished study prepared by Case Consulting Laboratories, Inc. 34 p.

46248002 Sinning, D. (2004) Leach Rate Determination of Pettit Marine Paint

Alumacoat SR Antifouling Paint 1461 Yellow Containing Zinc Omadine. Project Number: 390/71, ASTM/D/5108/90. Unpublished study prepared by Case Consulting Laboratories, Inc. 22 p.

46547403 Sinning, D. (2004) Leach Rate Determination of Pettit Marine Paint

Alumaspray + Aerosol Antifouling Paint 1763 Gray Co ntaining Zinc Omadine. Project Number: 390/78. Unpublished study prepared by Case Consulting Laboratories, Inc. 22 p.

46547404 Sinning, D. (2004) Leach Rate Determination of Pettit Marine Paint

Alumaspray + Aerosol Antifouling Paint 1863 Black Containing Zinc Omadine. Project Number: 390/77. Unpublished study prepared by Case Consulting Laboratories, Inc. 22 p.

46625103 Sinning, D. (2005) Leach Rate Determination of Cuprous Oxide 40% and

4.4% Zinc Omadine (Solvent) Island 77 Plus Black Antifouling Paint C ontaining Zinc Omadine. Project Number: 2450/09. Unpublished study prepared by Case Consulting Laboratories, Inc. 22 p.

46640501 Sinning, D. (2005) Leach Rate Determination of Cuprous Oxide Free with 4%

Zinc Omadine (Solvent) White Antifouling Paint Conta ining Zinc Omadine. Project Number: 2450/07. Unpublished study prepared by Case Consulting Laboratories, Inc. 22 p.

46640601 Sinning, D. (2005) Leach Rate Determination of Cuprous Oxide Free with

4.2% Zinc Omadine (Water Base) White Antifouling Paint Cont aining Zinc Omadine. Project Number: 2450/08. Unpublished study prepared by Case Consulting Laboratories, Inc. 22 p.

46934508 Serak, K.; Hanh, J. (2006) Determination of the Leach Rate of Econea from

Paint (International Copper Free) in Synthetic Seawater . Project Number: 49702, 49702/7. Unpublished study prepared by Analytical Bio

- Chemistry Labs., Inc. 62 p.

47039201 Schofield, D. (2007) International Copper Free, White Antifouling Paint

(Zinc Pyrithione) 45 Day Leaching Study. Project Number: STUDY/1304 560. Unpublished study prepared by Intertek ASG. 42 p.

47171303 Sinning, D. (2006) Leach Rate Determination of Pettit Marine Paint ULTIMA

SPC Antifouling Paint 1299 Blue Containing Zinc Omadine. Project Number: 390/81. Unpublished study prepared by Case C onsulting Laboratories, Inc. 26
p.

### 47171304 Sinning, D. (2006) Leach Rate Determination of Pettit Marine Paint ULTIMA SPC Antifouling Paint 1399 Green Containing Zinc Omadine. Project Number: 390/82. Unpublished study prepared by Case Consulting Laborator ies, Inc. 26 p.

47171305 Sinning, D. (2006) Leach Rate Determination of Pettit Marine Paint ULTIMA

SPC Antifouling Paint 1699 Red Containing Zinc Omadine. Project Number: 390/83. Unpublished study prepared by Case Consulting Laboratories, Inc. 26
p.
4718 8401 Sinning, D. (2006) Leach Rate Determination of Pettit Marine Paint Ultima

SPC Antifouling Paint 1899 Black Containing Zinc Omadine. Project Number: 390/84. Unpublished study prepared by Case Consulting Laboratories, Inc. 26 p.

47238912 Serak, K. (200 7) Determination of the Leach Rate of Organic Biocides from

Two Paints in Substitute Ocean Water: Seaguard HMF 1 and Seaguard HMF 2: HMC Antifouling Paint. Project Number: 49912, 49912/1. Unpublished study prepared by ABC Laboratories, Inc. 125 p.

4755080 1 Tunink, A. (2008) Determination of the Leach Rate of Organic Biocides from

Four Paint Colors, Code No. LAg 2007 025

- Black, Red, Blue, and Green in Substitute Ocean Water. Project Number: 63315, AGR/3766, ASTM/D/6903/07. Unpublished study prepared by AB C Laboratories, Inc. 98
p.

Copper Omadine



## 161

- 1 Hydrolysis

MRID Citation Reference

45774322 Fenn, R. (1999) Hydrolysis of (Pyridine

- 2,6

- Carbon 14) Copper Omadine: Final

Report: Lab Project Number: 40

- 96B10CUOM. Unpublished study prepared by A rch Chemicals, Inc. 106 p. {OPPTS 835.2120}



## 161

- 2 Photodegradation

- water

MRID Citation Reference

45774323 Fenn, R. (2000) Photolysis of (Pyridine

- 2,6

- Carbon 14) Copper Omadine: Final

Report: Lab Project Number: 56

- 98B10CUPT. Unpublished study prepared by Arch Chemicals, Inc. 185 p. {OPPTS 835.2240}

## 163

- 1 Leach/adsorp/desorption

MRID Citation Reference

45774327 Sun, P.; Fernando, Q.; Freiser, H. (1964) Formation Constants of Transition

Metal Complexes of 2

- Hydroxypyridine

- 1

- Oxi de and 2

- Mercaptopyridine

- 1

- Oxide. Analytical Chemistry 36(13):2485

- 2488.

45780508 Ritter, J. (2002) Adsorption/Desorption (Batch Equilibrium) Characteristics of

Copper Omadine. Unpublished study prepared by Arch Chemicals, Inc. 10 p. {OPPTS 835.1240, 83 5.1230} 

## ASTM D5108

- 90 Leaching from Treated Paint

45793501 Fenn, R. (2000) Leach Rate of Copper Pyrithione from Antifouling SeaQueen

Paint in Synthetic Seawater: Final Report: Lab Project Number: 71

- 00B10CUPT. Unpublished study prepared by Arch Chemica ls, Inc. 58 p.

45827702 Dahling, M. (2002) Leaching Rates of Copper Pyrithione from Antifouling

Seaqueen by Calculation Method: Lab Project Number: MD/8068

- 1/016. Unpublished study prepared by Jotun AS. 9 p.

46105308 Boeri, R.; Rondon, C.; Ward, T. (20 03) Leach Rate of Copper Omadine from

Interswift 655 (Code Number BMA004) Dark Red in Synthetic Seawater. Project Number: 2617/IP. Unpublished study prepared by T.R. Wilbury Laboratories, Inc. 44 p.

46105309 Boeri, R.; Rondon, C.; Ward, T. (2003) Leach Ra te of Copper Omadine from

Interswift 655 (Code Number BMA008) Brown in Synthetic Seawater. Project Number: 2618/IP. Unpublished study prepared by T.R. Wilbury Laboratories, Inc. 44 p.

47107709 Boeri, R.; Rondon, C.; Ward, T. (2003) Leach Rate of Copper Om adine from

Interswift 655 (Code Number BMA004) Dark Red in Synthetic Seawater. Project Number: 2617/IP. Unpublished study prepared by T.R. Wilbury Laboratories, Inc. 44 p.

47107710 Boeri, R.; Rondon, C.; Ward, T. (2003) Leach Rate of Copper Omadine from

I nterswift 655 (Code Number BMA008) Brown in Synthetic Seawater. Project Number: 2618/IP. Unpublished study prepared by T.R. Wilbury Laboratories, Inc. 44 p.

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- off Date : 11/17/10 DP Barcode No. : D344371