Document ID: EPA-HQ-OPP-2007-1151-0009
Agency: epa
Document Type: Supporting & Related Material
Title: 
Posted Date: 2008-01-16T05:00Z

ENVIRONMENTAL PROTECTION AGENCY

WASHINGTON, D.C. 20460

OFFICE OF

                                                                        
                                    PREVENTION, PESTICIDES AND 

                                                                        
                                             TOXIC SUBSTANCES

					

January 9, 2008

MEMORANDUM  

                                                                        

	

SUBJECT:	Environmental Fate Assessment of Diiodomethyl p-tolyl sulfone 
for RED

Case No.:  4009		DP Barcode:  344849

FROM:		James Breithaupt, Agronomist

Environmental Risk Branch II

Environmental Fate and Effects Division (7507P)

TO:			Marshall Swindell, Risk Manager

K. Avivah Jakob, Risk Manager Reviewer

Regulatory Management Branch I

Antimicrobials Division (7510P)

 

THRU:	Richard C. Petrie, Team Leader, Team Three

Risk Assessment and Science Support Branch (RASSB)

Antimicrobials Division (7510P)

Norman Cook, Branch Chief

Risk Assessment and Science Support Branch (RASSB)

Antimicrobials Division (7510P)

Chemical Name				PC Code	CAS#		Common Name

(p-tolyl diiodomethyl sulfone			101002	20018-09-1	Amical 48™

  	

Environmental Fate Science Chapter and Fate Assessment on Diiodomethyl
p-tolyl sulfone technical is submitted for Reregistration.

Diiodomethyl p-tolyl sulfone Technical

ENVIRONMENTAL FATE SCIENCE CHAPTER

EXECUTIVE SUMMARY

	Amical 48™ Technical is an anti-fouling preservative that contains
95% of the active ingredient (p-tolyl diiodomethyl sulfone).  It is used
for food handling/storage establishments premises and equipment (drains,
grease traps), Materials Preservatives [Paints (in-can), coatings, fire
retardant, adhesives, caulks, sealants, slurries, dispersions/emulsions/
solutions/suspensions, rubber products, plastic/PVC/vinyl products,
hides/leathers/leather products, textiles, papermaking, paper and
paperboard, nitrocellulose, melamine formaldehyde thermosetting resins,
Industrial Processes and Water Systems (septic systems), and Wood
Preservatives (mildew, sapstain, and wood-rotting organisms for wood
above ground, no pressure treatment).  

	Diiodomethyl p-tolyl sulfone is a wettable powder that is slightly
soluble in water.  The chemical structure of diiodomethyl p-tolyl
sulfone is as follows:

Figure 1.  Structure of Diiodomethyl p-tolyl sulfone

 

Figure 2.  Structure of MIMPTS (monoiodomethyl-p-tolylsulfone)

 

Figure 3.  Structure of MPTS (methyl-p-tolylsulfone)

 

Figure 4.  Structure of PTSA (p-toluene sulfinic acid)

 

Figure 5.  Structure of PTS-O-A (p-toluene sulfonic acid)	

	Diiodomethyl p-tolyl sulfone (Figure 1) is stable to hydrolysis at pH
5, but degraded with half-lives of 2-4 days at pH 7 and 9.  MIMPTS
(Figure 2, Monoiodomethyl-p-tolylsulfone, parent minus one iodo group)
was the major degradate formed, and increased until the end of the study
(30 days).  MPTS (Figure 3, methyl-p-tolylsulfone, parent minus both
iodo groups) and PTSA (Figure 4, p-toluene sulfinic acid, parent minus
methyl group) reached minor concentrations.  Soil photolysis half-lives
of 13 days (linear) and 5.3 (non-linear) were observed for parent
compound. MIMPTS was stable in the dark control but degraded with a
half-life of 12.5 day in irradiated sample.  Volatiles and
non-extractables were negligible.

	Degradation by microorganisms will reduce diiodomethyl p-tolyl sulfone
concentrations in the environment, but residues are expected to
partition to water in the presence of soil or sediment.   In aerobic
soil (the top layer of non-flooded soil), the non-linear parent, MIMPTS,
and MPTS half-lives were 1.5, 32, and 53 days, respectively.   The
linear half-life of MPTS was 173 days.  PTS-O-A (p-toluene sulfonic
acid, parent minus methyl plus added oxygen, Figure 5) did not exceed
0.7 % in the study.  In the anaerobic soil metabolism study (the second
layer of soil), the half-lives of parent diiodomethyl p-tolyl sulfone
were 1.7 and 4.2 days in aerobic (non-flooded) and anaerobic (flooded
soil) portions of the study, respectively.  Diiodomethyl p-tolyl sulfone
was found in equal portions in water and sediment.  MIMPTS was a major
degradate with a half-life of 21 days and was found predominantly in
water.  MPTS reached 81 % by the end of the study and was primarily
found in water.  Anaerobic aquatic metabolism (representing bottom
sediment) degrades parent and MIMPTS with total system half-lives of 9.6
and 11 days, respectively.  MPTS was the terminal metabolite and
increased to 95 % by 4-6 months.  Aqueous residues were greater than
sediment residues for parent, MIMPTS, and MPTS for 7, 180, and 60 days,
respectively.  

	Diiodomethyl p-tolyl sulfone was mobile in columns of soil that were
leached with water.  The amounts of parent compound that leached through
12-inch columns were 73, 84, 34, and 8 % in sand, silt loam, sandy loam,
and clay soils.  An average of 2, 1.5, 5, and 8 % of applied compound
was present in each inch of the columns, respectively.  

The Log Kow (Log P) for parent diiodomethyl p-tolyl sulfone is 2.66,
and the estimated (EPI-SUITE) Log Kow values for MIMPTS, MPTS, and PTSA
were 2.2, 1.1, and 0.56, respectively.  None of these compounds are
expected to bioconcentrate significantly because the Log Kow values are
below 3.0.  

	An average of 43 % of diiodomethyl p-tolyl sulfone from wooden tongue
depressors leached into pH 5, 7, 9 unfiltered buffers over a 30-day
study (median of 42 %).  Maximum residues in water were observed at day
zero, followed by a decrease to the minimum values at day 7 and a
general increase.  In filtered samples, the aqueous residues averaged
4.3 %, indicating that some sorption to organic materials may occur in
the environment.  

	There was no inhibition of microorganisms in sewage sludge treated at 9
mg/l.

	

I.	Environmental Fate Assessment

	A.	Abiotic

Diiodomethyl p-tolyl sulfone (Figure 1) forms sequential metabolites
MIMPTS (parent minus one iodo group, Figure 2), MPTS (parent minus both
iodo groups, Figure 3), PTSA (parent minus methyl group, Figure 4), and
PTS-O-A (MPTS minus methyl plus oxygen, Figure 5).  The degree of
formation of metabolites depends on the level of oxidation potential
present in the test system.  Diiodomethyl p-tolyl sulfone and its
metabolites are largely present in water in the presence of
soil/sediment and degradation forms compounds that are more polar and
water soluble than parent compound.   

Diiodomethyl p-tolyl sulfone is stable to hydrolysis at pH 5, but
degrades rapidly in pH 7 and 9 buffered solutions with linear half-lives
of 2.1-3.6 days.  The major degradate was MIMPTS, whose concentrations
did not decline in the study and reached 90-100 % of applied by the end
of the study.  The minor degradates MPTS and PTSA were formed in the
study.  Soil photolysis half-lives of 13 days (linear) and 5.3
(non-linear) were observed for parent compound. MIMPTS was stable in the
dark control but degraded with a half-life of 12.5 day in irradiated
sample.  Volatiles and non-extractables were negligible.

	B.	Biotic

	Under aerobic soil conditions, parent Diiodomethyl p-tolyl sulfone and
MIMPTS degraded with non-linear half-lives of 1.5 and 32 days in sandy
loam soil, respectively.  The next sequential metabolite was MPTS which
degraded with calculated non-linear and linear half-lives of 53 (poor
fit) and 173 (better fit) days, respectively.  The metabolite PTS-O-A
(MPTS minus methyl plus oxygen) did not exceed 0.7 % in the study. 
Based on the increase in non-extractable residues, the decrease in
extractable residues, and the formation of CO2, complete mineralization
of some of the product in aerobic soil was occurring.  

In sandy loam soil, diiodomethyl p-tolyl sulfone degraded with
calculated half-lives of 1.7 and 4.2 days in aerobic and anaerobic
conditions, respectively.  Diiodomethyl p-tolyl sulfone was found in
equal portions in water and soil in the anaerobic portion of the study. 
 MIMPTS degraded with a non-linear half-life of 21 days in the anaerobic
portion of the study and was found primarily in the water phase.  MPTS
increased to 81 % by the end of the study (60 days) and was found in the
water instead of the sediment.  PTS-O-A was not formed in significant
quantities.  Extractable residues declined in the study,
non-extractables were not in significant quantities, and water soluble
residues increased to 84 % by 60 days.  The lack of non-extractables and
the increase in water soluble residues is consistent with the formation
of metabolites with increasing water solubility.  Volatiles did not
exceed 0.05 % indicating that complete mineralization or volatility of
organic compounds did not occur.

Under anaerobic aquatic conditions (sandy loam sediment, water, and
nitrogen atmosphere), the total system, non-linear half-lives of
diiodomethyl p-tolyl sulfone and MIMPTS were 9.6 and 11 days,
respectively.  Parent compound was associated more with water than
sediment through 7 days and more in sediment afterwards.  MIMPTS reached
16.2 % by 7 days, and then declined to <1 % by 3-6 months.  MIMPTS was
associated more in water than sediment for 60 days and then in equal
portions thereafter.  MPTS increased to 94.5 by 4-6 months, and was
associated with water rather than sediment over the duration of the
study.  PTS-O-A did not reach significant levels in the study. 
Extractable residues were 23-31 % (0-14 days) and 16-18 % by 30-180
days, and non-extractable residues never exceeded 2 %.  Water soluble
residues ranged from 68 to 85 % and volatiles did not exceed 0.8 %.

In columns of sand, silt loam, sandy loam, and clay soils, 73, 84, 34,
and 8 % of radioactivity passed through the columns into the leachate,
respectively.  An average of 2, 1.5, 5, and 8 % of applied diiodomethyl
p-tolyl sulfone was detected in each inch of the 12-inch columns.  These
results indicate that diiodomethyl p-tolyl sulfone residues will
eventually leach through the columns.  

	An average of 43 % of diiodomethyl p-tolyl sulfone from wooden tongue
depressors leached into pH 5, 7, 9 unfiltered buffers over a 30-day
study (median of 42 %).  Maximum residues in water were observed at day
zero, followed by a decrease to the minimum values at day 7 and a
general increase.  The wood extract accounted for 2.1-6 % of applied for
pH 5, 7, and 9.  In filtered samples, the aqueous residues averaged 4.3
%, indicating that some sorption to organic materials may occur in the
environment.  

There was no inhibition of microorganisms in sewage sludge treated at 9
mg/l.

APPENDIX

Environmental Fate Data for Diiodomethyl p-tolyl sulfone Technical

A.	Environmental Fate Guideline Studies

	1.	Hydrolysis (Guideline Number OPPTS 161-1, MRID No.  43008701)

	This hydrolysis study, submitted under MRID No. 43008701, was reviewed
by the Agency and found to be acceptable for the active ingredient,
di-iodomethyl-p-tolylsulfone.  The hydrolysis data requirement for
diiodomethyl p-tolyl sulfone technical has been fulfilled.

Amical 48 (di-iodomethyl-p-tolylsulfone, Figure 1) is stable to
hydrolysis at pH 5, but degrades rapidly in pH 7 and 9 buffered
solutions with linear half-lives of 2.1-3.6 days.  The major degradate
was MIMPTS (Monoiodomethyl-p-tolylsulfone, parent minus 1 iodo group,
Figure 2).  MIMPTS concentrations did not decline in the study and
reached 90-100 % of applied by the end of the study (14-30 days). 
However, some MIMPTS did degrade to the minor degradates MPTS
(methyl-p-tolylsulfone, parent minus both iodo group, Figure 3) and PTSA
(p-toluene sulfinic acid, parent minus methyl group, Figure 4).   MPTS
and PTSA were formed at <2.8 and <4.4 % of applied, respectively (MRID
43008701).  

Photodegradation in Water and on Soil (Guideline Nos. OPPTS 161-2 and
161-3, Waived)

	The Agency is waiving the data requirement for the photodegradation of
diiodomethyl p-tolyl sulfone Technical in water.  The active ingredient
is hydrolytically unstable (2-4 days) and rapidly degrades.  The aerobic
soil metabolism study also demonstrates a half-life of 1.5 days.  
However, the registrant submitted a soil photolysis study (Madsen, S.
and M.D. Williams.  ABC Report No. 38727, no MRID).   Soil photolysis
half-lives of 13 days (linear) and 5.3 (non-linear) were observed for
parent compound. MIMPTS was stable in the dark control but degraded with
a half-life of 12.5 day in irradiated sample.  Volatiles and
non-extractables were negligible.	

	3.	Aerobic Soil Metabolism (Guideline No. OPPTS 162-1, MRID No.
41765405)

	This aerobic soil metabolism study, submitted under MRID No. 41765405,
was reviewed by the Agency and found to be supplemental for the active
ingredient, di-iodomethyl-p-tolylsulfone.  

Under aerobic soil conditions, parent diiodomethyl p-tolyl sulfone
degraded with a non-linear half-life of 1.5 days in sandy loam soil. 
Parent compound  declined from 87 % of applied at time zero to 1.3-3 %
by 60-366 days (end of study).  The first sequential metabolite was
MIMPTS (Figure 2), which reached a maximum of 65 % by day five and
declined to 1.2-2.1 % by 182-366 days.  It declined with a calculated
non-linear (formation/decline) half-life of 32 days.   The next
sequential metabolite was MPTS (Figure 3), which reached about 56 % of
applied by 121 days and declined to about 20 % of applied by 366 days. 
The calculated non-linear and linear half-lives were 53 and 173 days,
respectively.  The 173-day linear half-life more closely represents the
MPTS data.  The metabolite PTS-O-A (parent minus methyl plus oxygen,
Figure 5) did not exceed 0.7 % in the study.  Non-extractable residues
reached consistent levels of 18-27 % by 21-366 days, and extractable
residues declined from 77 % (21 days) to 25 % (366 days).  Volatiles
(virtually all CO2) increased to 53 % of applied by 366 days, indicating
complete mineralization of some residues (MRID 41765405).

	4.	Anaerobic Soil Metabolism (Guideline No. OPPTS 162-2, MRID No.
41765406)

	This anaerobic soil metabolism study, submitted under MRID No.
41765406, was reviewed by the Agency and found to be supplemental for
the active ingredient, di-iodomethyl-p-tolylsulfone.  

Under aerobic soil and anaerobic conditions, diiodomethyl p-tolyl
sulfone degraded with half-lives of 1.7 and 4.2 days, respectively. 
Parent compound was found in equal portions in water and soil in the
anaerobic portion of the study.  MIMPTS (Figure 2) was the first major
metabolite, and degraded under anaerobic conditions with a non-linear
half-life of 21 days.  Aqueous residues were about 4.6 times higher than
those in sediment.  MPTS (Figure 3) increased to 81 % by the end of the
study (60 days) and was found in the water over the sediment (4X). 
PTS-O-A (Figure 5) was formed at <1.4 % of applied in the study. 
Extractable residues declined from 99 % at day zero to 15 % at 60 days
and non-extractables did not exceed 5 % in the study.  Water soluble
residues increased from 56 % at the start of the anaerobic period (15
days) and increased to 84 % by 60 days.  The lack of non-extractables
and the increase in water soluble residues is consistent with the
formation of metabolites with increasing water solubility.  Volatiles
did not exceed 0.05 % (MRID 41765406).

	5.	Anaerobic Aquatic Metabolism (Guideline No. OPPTS 162-3, MRID No.
42177201)

	This anaerobic aquatic metabolism study was reviewed by the Agency and
found to be supplemental for the active ingredient
di-iodomethyl-p-tolylsulfone. 

	

Under anaerobic aquatic conditions (sandy loam sediment, water, and
nitrogen atmosphere), the total system, non-linear half-lives of
diiodomethyl p-tolyl sulfone and MIMPTS were 9.6 and 11 days,
respectively.  Parent compound was associated more with water than
sediment through 7 days and more in sediment afterwards.  MIMPTS reached
16.2 % by 7 days, and then declined to <1 % by 3-6 months.  MIMPTS was
associated more in water than sediment for 60 days and then in equal
portions thereafter.  MPTS increased to 94.5 by 4-6 months, and was
associated with water rather than sediment over the duration of the
study.  PTS-O-A did not reach significant levels in the study. 
Extractable residues were 23-31 % (0-14 days) and 16-18 % by 30-180
days, and non-extractable residues never exceeded 2 %.  Water soluble
residues ranged from 68 to 85 % and volatiles did not exceed 0.8 % (MRID
42177201).

	6.	Aerobic Aquatic Metabolism (Guideline No. OPPTS 162-4, No data)

No data have been submitted.

 

	7.	Adsorption/Desorption (Guideline No. OPPTS 163-1, MRID No. 41765407)

	This soil column leaching study was reviewed by the Agency and found to
be supplemental for the active ingredient di-iodomethyl-p-tolylsulfone. 
  Batch equilibrium studies using parent compound are not possible
because of hydrolytic instability.  

	In columns of sand, silt loam, sandy loam, and clay soils, 73, 84, 34,
and 8 % of radioactivity passed through the columns into the leachate,
respectively.  An average of 2, 1.5, 5, and 8 % of applied parent
compound was detected in each inch of the 12-inch columns.  These
results indicate that diiodomethyl p-tolyl sulfone residues will
eventually leach through the columns (MRID 41765407).  

	8	Bioaccumulation in Fish (Guideline No. OPPTS 165-4, Agency Estimated
BCF) (No MRID Number))

	Based on the Log P (Log Kow) of 2.66 (<3), significant bioconcentration
in fish is not likely.  Based on the Log P (assuming stability of
parent), the maximum bioconcentration factor is 11X, which is far less
the level of concern of 1,000X.  Also, the lack of persistence in
hydrolysis (2-4 days) and the formation of metabolites with higher
polarity and water solubility  than parent will prevent significant
bioconcentration.

  

 	9.	Special Leaching Study (American Wood Preservers’ Association
Standards-1998, Standard Method E11-97, MRID No. 43997001)

	This leaching study was reviewed by the Agency and was rejected because
non-standard wood (tongue depressors) was used in the study.  The wood
leaching data requirement for diiodomethyl p-tolyl sulfone Technical
should be satisfied using the AWPA E11-97 protocol.  

	Puritan® tongue depressors were treated with diiodomethyl p-tolyl
sulfone stock solution to achieve a 1 % concentration in the wood
(weight basis).  The treated wood sticks were placed into pH 5 (acetate
buffer), pH 7 (HEPES buffer), pH 9 (Borate buffer), 0.1 N HCl, and into
deionized water.  In unfiltered buffers, the aqueous residues within
each buffer averaged 46, 42, 43, 42, and 40 % of the applied,
respectively.  Within each test interval, the averages of aqueous
residues were 53, 33, 40, 42, and 46 % for day 0, 7, 14, 21, and 30,
respectively.  Maximum residues in water were observed at day zero,
followed by a decrease to the minimum values at day 7 and a general
increase.  The wood extract accounted for 2.1-6 % of applied for pH 5,
7, 9, HCl, and water, respectively.  In filtered samples, the aqueous
residues generally declined from day zero (mean of 8 %), declined to
about 1 % at day 7, and increased to 6 % by 30 days.  The average
percent aqueous recovery in each buffer was 3-7 %.  Apparently, wood
fragments sorbed the compound in the water.  MIMPTS (Figure 2) was only
major (10 %) degradate, and minor amounts of PTSA (Figure 4), PTS-O-A
(Figure 5) and MPTS (Figure 3) were formed.  The median ratio of
unfiltered:filtered concentrations was 11, which could have occurred
either from suspended wood particles or the filter itself (MRID
43997001).

Inhibition of Sewage Sludge Respiration (OECD Test Method 209), Gonsior,
2002.

The potential for diiodomethyl-p-tolylsulfone to inhibit the respiration
of municipal activated sludge was evaluated using the test method OECD
209 “Activated Sludge, Respiration Inhibition Test.” This test
method assesses the effect of a test chemical on microorganisms by
measuring the respiration rate under defined conditions in the presence
of different concentrations of the test chemical following a 3-hour
contact period. Diiodomethyl p-tolyl sulfone , at a nominal
concentration of 9 mg/L (approximately 90-fold higher than the reported
water solubility of 0.1 mg/L), did not inhibit the respiration rate of
the activated sludge compared to control mixtures (no test chemical
added).Data Gap:  See Table below.

Environmental Fate Data Requirements for Diiodomethyl p-tolyl sulfone
Technical

OPP Guideline	

Data Requirement	

MRID No.	

Data Requirement Status

161-1	

Hydrolysis	41765404

43008701	Satisfied

161-2	

Photodegradation in Water	None	Not required

161-3	Photodegradation on Soil	Madsen and  Williams.  ABC Report No.
38727, no MRID)	Acceptable but not required

162-1	Aerobic Soil Metabolism	41765405	Acceptable but not required

162-2	Anaerobic Soil Metabolism	41765406	Acceptable but not required

162-3	

Anaerobic Aquatic Metabolism	42177201	Acceptable but not required

162-4	

Aerobic Aquatic Metabolism	None	Not required

163-1	

Adsorption/Desorption	41765407	Acceptable but not required

OECD

305

	

Bioaccumulation in Fish	None	Not required

ASTM D5108-90

AWPA E11-06 protocol study required	

Special Leaching Study	43997001	Rejected because of non-standard wood
used in test 

OECD 209	Inhibition of Sewage Sludge Respiration	Gonsior, 2002, no MRID
Acceptable but not required

BIBLIOGRAPHY

MRID					CITATION

161-1       Hydrolysis

41765404	Carpenter, M. (1988) Hydrolysis as a Function of pH at
25(degrees)C of carbon 14|-Amical-48: Lab Project Number: 36019. Unpub-
lished study prepared by Analytical Bio-Chemistry Labs., Inc. 756 p. 

43008701	Williams, M.; Heim, L. (1993) Hydrolysis of AMICAL 48 as a
Function of pH at 25 (degrees) C: Lab Project Number: 40886. Unpublished
study prepared by ABC Laboratories, Inc. 63 p. 

161-3		Photodegradation on Soil

Madsen, S. and M.D. Williams.  1991.  Determination of the Photolysis
Rate of 14C-Amical 48 on the Surface of Soil.  ABC Laboratories Final
Report No. 38727.  No MRID.

162-1       Aerobic soil metabolism

41765405	Cranor, W. (1990) Aerobic Soil Metabolism of carbon 14|-Abbott-
9248 (Amical 48): Lab Project Number: 36608. Unpublished study prepared
by Analytical Bio-Chemistry Labs., Inc. 955 p. 

162-2       Anaerobic soil metabolism

41765406	Madsen, S.; Williams, M. (1990) Anaerobic Soil Metabolism of
carbon 14|-Amical 48: Lab Project Number: 38730. Unpublished study
prepared by Analytical Bio-Chemistry Labs., Inc. 461 p. 

162-3       Anaerobic aquatic metab.

42177201	Madsen, S.; Williams, M. (1991) Anaerobic Aquatic Metabolism of
carbon 14| Amical 48: Final Report: Lab Project Number: 38729.
Unpublished study prepared by ABC Labs, Inc. 532 p. 

163-1       Leach/adsorp/desorption

41765407	Daly, D.; Cranor, W. (1987) Leaching Characteristics in Soil
with carbon 14|-Amical-48 (Abbott-9248): Lab Project Number: 36021.
Unpublished study prepared by Analytical Bio-Chemistry Labs., Inc. 277
p. 

Special Leaching from Wood (ASTM D5108-90)

43997001 	Williams, M.; Bradley, A. (1996) Aqueous Availability of
AMICAL 48: Final Report: Lab Project Number: 42782: ABC 42782.
Unpublished study prepared by ABC Laboratories Europe, Ltd. 78 p.  

Inhibition of Sewage Sludge Respiration

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No MRID.  

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