Document ID: EPA-HQ-OPP-2007-0540-0005
Agency: epa
Document Type: Supporting & Related Material
Title: 
Posted Date: 2007-07-18T04:00Z

UNITED STATES ENVIRONMENTAL PROTECTION AGENCY

WASHINGTON, D.C. 20460

 OFFICE OF

                                                                        
                                    PREVENTION, PESTICIDES AND 

         TOXIC SUBSTANCES

June 28, 2007

MEMORANDUM

SUBJECT:	Environmental Fate Science Chapter for the Bromonitrostyrene
Reregistration Eligibility Decision (RED) Document

			DP Barcode:	336286	Reregistration Case No.:  2065

FROM:	Srinivas Gowda, Microbiologist/Chemist

Risk Assessment and Science Support Branch (RASSB)

Antimicrobials Division (7510P)

TO:			Mark Hartman, Branch Chief

Diane Isbell, Team Leader

ShaRon Carlisle, Chemical Review Manager

Regulatory Management Branch II

Antimicrobials Division (7510P)

Jenny Tao, Risk Assessor

Risk Assessment and Science Support Branch (RASSB)

Antimicrobials Division (7510P)

THRU:	Siroos Mostaghimi, Team Leader, Team one

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 Names

		      beta-Bromo-beta-	  101401	7166-19-0	Bromonitrostyrene

		         nitrostyrene

Attached is the Environmental Fate Science Chapter for the
Bromonitrostyrene RED Document.

Attachment:  Environmental Fate Science Chapter for the
Bromonitrostyrene RED Document.

BROMONITROSTYRENE

REREGISTRATION ELIGIBILITY DECISION

ENVIRONMENTAL FATE SCIENCE CHAPTER

EXECUTIVE SUMMARY

	Bromonitrostyrene (Figure 1) is Fungicide, Slimicide, Molluscide,
Mildewcide, Algaecide, and Microbicide/Microbiostat.  Bromonitrostyrene
is used in the manufacture of a variety of materials as a preservative
such as cleaners, adhesives, paper and paperboard (food contact), water
based coatings, paints, inks and dyes.  Industrial process and water
system uses include evaporative condenser water and systems, pulp and
paper mill water systems, brewery pasteurizer water and metal working
machinery coolant systems.  Bromonitrostyrene containing products are
also approved for use in aquatic areas such as ponds, waste water
systems, sewage water and cooling tower water.  Bromonitrostyrene (TGAI)
is a yellow powder and is soluble in water at 0.001g/100 ml (10 ppm) at
25˚C.  The chemical structure of Bromonitrostyrene (Figure 1) is as
follows:

 

Figure 1.  Structure of Bromonitrostyrene

	Six of the required guideline studies for an environmental fate
assessment have been submitted for Bromonitrostyrene.  The Agency is
using the six environmental fate studies for the fate assessment of
Bromonitrostyrene to fulfill the re-registration requirements.

	When Bromonitrostyrene is introduced into the environment, it is most
likely to degrade rapidly through hydrolysis and photodegradation.  In
abiotic and aqueous buffered conditions over the pH 5-9 range at 25°C,
the half-lives for Bromonitrostyrene in pH 5, pH 7 (HEPES), pH 7 (TRIS),
and pH 9 buffer solutions were 10.32 hours, 6.17 hours, 4.68 hours, and
3.40 hours, respectively.  The major transformation product in all
solutions was benzaldehyde.  2-Bromo-2-nitro-1-phenyl ethanol (as a
mixture of diastereomers; degradate 1) was a major transformation
product in the pH 5 buffer solutions and a minor transformation product
in the other buffer solutions.  Benzoyl formic acid (degradate 2) was a
major transformation product in the pH 9 buffer solutions, and a minor
transformation product in the other buffer solutions.  The only
identified minor transformation product was benzoic acid, which was
found in all buffer solutions.  Bromonitrostyrene also photodegraded
rapidly in pH 5 aqueous buffer solutions with a calculated half-life of
1.70 hours in irradiated samples, and 10.4 hours in the dark controls. 
Three major transformation products were identified in the irradiated
system: 2-phenyl-2-isonitroso acetic acid, benzaldehyde, and
2-bromo-2-nitro-1-phenyl ethanol.  One minor transformation product,
benzoyl formic acid, was also identified in the irradiated system only. 
Benzaldehyde and 2-bromo-2-nitro-1-phenyl ethanol were also identified
in the dark controls, but attributed largely to hydrolysis of the
parent.

	Under biotic conditions, the degradation rate of Bromonitrostyrene in
aerobic and anaerobic aquatic river water-sediment systems could not be
determined.  The half-lives for Bromonitrostyrene were not calculated
because data were only provided for the first two sampling intervals. 
Two transformation products were identified: benzaldehyde and
bromonitromethane.  Uncharacterized total radioactivity partitioned into
the sediment in both aerobic and anaerobic systems, with sediment:water
ratios of 12-27:1 by 14 days.

	Bromonitrostyrene was slightly mobile to moderately mobile in soil. 
Freundlich adsorption Kd values were 4.56, 4.57, 8.99, and 13.5 for the
silty clay loam soil, silt loam soil, sandy loam soil, and sand
sediment, respectively; corresponding Freundlich Koc values were 770,
1570, 1180, and 853, respectively.  The estimated Koc value for
Bromonitrostyrene using an HPLC method was 3.0.  In an unaged column
leaching study, Bromonitrostyrene desorbed readily from soils with a Kd
range of 17 to 126.

	Bromonitrostyrene is not likely to bioaccumulation in fish (log Kow
2.34).  No signs of distress or death in Bluegills were observed after
30 days of exposure to 0.05 ppm and 0.1 ppm of Bromonitrostyrene, and
after 24 weeks of exposure to 2 ppm of Bromonitrostyrene.

 α-carbon-labeled [14C]Bromonitrostyrene (radiochemical purity 98.0%)
degraded rapidly in sterile aqueous buffer solutions adjusted to pH 5
(acetate), pH 7 (HEPES), pH 7 (TRIS), and pH 9 (borate) that were
incubated in darkness at 25°C ± 1°C for 24 hours.  In the pH 5 buffer
solution, the parent was 107.8% of the applied at time 0, declined to
70.0% at 5 hours, and was 19.9% at 24 hours.  In the pH 7 HEPES buffer
solution, the parent was 107.9% of the applied at time 0, declined to
69.2% at 5 hours, and was 7.4% at 24 hours.  In the pH 7 TRIS buffer
solution, the parent was 95.8% of the applied at time 0, declined to
60.2% at 5 hours, and was 3.1% at 24 hours.  In the pH 9 buffer
solution, the parent was 101.0% of the applied at time 0, declined to
65.5% at 3 hours, to 47.2% at 5 hours, and was 0.89% at 24 hours.  The
half-lives for Bromonitrostyrene in pH 5, pH 7 (HEPES), pH 7 (TRIS), and
pH 9 buffer solutions were 10.32 hours, 6.17 hours, 4.68 hours, and 3.40
hours, respectively.  The major transformation product in all solutions
was benzaldehyde, which was a maximum of 83.7%, 89.7%, 99.9%, and 74.0%
of the applied at 24 hours post treatment in the pH 5, pH 7 (HEPES), pH
7 (TRIS), and pH 9 buffer solutions, respectively. 
2-Bromo-2-nitro-1-phenyl ethanol (as a mixture of diastereomers;
degradate 1) was a major transformation product in the pH 5 buffer
solutions only, with a maximum of 11.8% at 3 hours, and 2.6% at 24
hours.  In the other buffer solutions, 2-bromo-2-nitro-1-phenyl was a
maximum of 2.2-4.4%.  Benzoyl formic acid (degradate 2) was a major
transformation product in the pH 9 buffer solution only, with a maximum
of 14.0% at 24 hours.  In the other buffer solutions, benzoyl formic
acid was a maximum of 2.6-4.8%.  The only identified minor
transformation product, benzoic acid, was a maximum of 0.2-0.8% in the
four buffer solutions.  An unidentified minor transformation product
(degradate 3) was a maximum of 0.2-4.0% in the four buffer solutions. 
The hydrolysis guideline requirements (OPP 161-1) have been fulfilled by
this study (MRID Nos. 423614-03 and 423614-04, supplemented by MRID No.
425385-01 for metabolite identification).

	In a supplemental hydrolysis study (MRID 124516), the half-life of
Bromonitrostyrene (labeling and purity not reported) was estimated at
5.36 hours using UV detection (pH not stated or controlled).  In another
supplemental study (EFED Document No. 2020704), the half-life of
Bromonitrostyrene applied at 10 ppm in water at pH 9, was 5.3 hours;
benzaldehyde and bromonitromethane were hydrolysis products.  In another
supplemental hydrolysis study (MRID No. 124521), Bromonitrostyrene
(labeling and purity not reported) was applied at a rate of 10 ppm to
distilled water and Passaic river water at pH 5, 7, and 9 for up to 24
hours.  In the distilled water, the rate of hydrolysis was fastest at pH
9.  The same trend was observed in the river water, but the degradation
occurred faster in the river water than the distilled water. 
Transformation products were not identified.  Half-lives were not
determined, however, hydrolysis was rapid.  In an unaccessioned
supplemental hydrolysis study (EFED Document No. 2020699),
Bromonitrostyrene (labeling and purity not reported) was applied at a
rate of 10 ppm to water buffered at pH 9 for up to 7 hours and analyzed
for Bromonitrostyrene, benzaldehyde and bromonitromethane.  The study
concluded that degradation takes place with rapid build-up of
degradation products and that there is room for error based on the total
recoveries.

of α-carbon-labeled [14C]Bromonitrostyrene (radiochemical purity 98.5%)
was studied in sterile pH 5 aqueous buffer solutions exposed to
artificial light for 12 hours (application rate, light/dark cycles, and
irradiation source were not reported).  The calculated half-life for
Bromonitrostyrene in the pH 5 solutions was 1.70 hours in the irradiated
samples, and 10.4 hours in the dark controls.  Three major
transformation products were identified: 2-phenyl-2-isonitroso acetic
acid, benzaldehyde, and 2-bromo-2-nitro-1-phenyl ethanol. 
2-Phenyl-2-isonitroso acetic acid was identified only in the irradiated
system, increasing to a maximum of 36.6% of the applied at 5 hours, then
declined to 24.1% at 12 hours.  Benzaldehyde was a maximum of 72.9% and
49.6% at 12 hours in the irradiated and dark controls, respectively. 
2-Bromo-2-nitro-1-phenyl ethanol (as a mixture of isomers) was in a
maximum of 15.8% at 1 hour in the irradiated and dark controls.  The
presence of benzaldehyde and 2-bromo-2-nitro-1-phenyl ethanol in the
dark controls was attributed largely to hydrolysis of the parent.  One
minor transformation product, benzoyl formic acid, was a maximum of 6.5%
in the irradiated samples only.  The photodegradation in water guideline
requirements (OPP 161-2) have been fulfilled by this study (MRID Nos.
423614-01 and 423614-02, supplemented by MRID 425385-02 for metabolite
identification).

Biotic

α-carbon-labeled [14C]Bromonitrostyrene (radiochemical purity ca. 96%)
was applied at a nominal rate of 10.3 mg/L to a river water-sediment
system from Florida and incubated under aerobic (air) or anaerobic
(nitrogen) conditions for 14 days in darkness at 24.0°C ( 1.1(C.  The
water:sediment ratio was 3:1 (75 mL water:25 g dry wt. sediment).  The
test system consisted of glass Erlenmeyer flasks (250-mL) containing
treated water and sediment attached to a volatile trapping system for
the collection of CO2 and volatile organic compounds. Samples were
collected after 2 hours, 1, 2, 4, 7, and 14 days.  Under aerobic and
anaerobic conditions, the overall recovery of radiolabeled material in
the total system averaged 73.0 ( 26.4%, and 57.87 ( 17.04% of the
applied, respectively, with no discernable pattern of decline but a
large variability within replicates.  In the aerobic system, the overall
recovery in the water decreased from an average of 20.1% at 2 hours to
1.9% at 14 days; and the recovery in the sediment increased from an
average of 36.3-53.0% at 2 hours-1 day, to a maximum of 56.6% at 4 days,
and was 50.4% at 14 days. Volatiles reached a maximum of 31.6% at 14
days.  In the anaerobic system, overall recovery in the water increased
from 16.2% at 2 hours, to a maximum of 21.5% at 1 day, and then declined
to 3.2% at 14 days; and the recovery in the sediment increased from
25.6% at 2 hours, to a maximum of 67.8% at 4 days, then declined to a
minimum of 11.8% at 7 days before increasing to 39.4% at 14 days. 
Volatiles reached a maximum of 21.4% at 14 days.  Uncharacterized total
radioactivity partitioned into the sediment in both aerobic and
anaerobic systems, with sediment:water ratios of 12-27:1 by 14 days.

The half-lives for Bromonitrostyrene were not calculated for either
system because radioactivity was characterized on for the first two
sampling intervals (2 hours and 1 day).  Two transformation products
were identified in both systems: benzaldehyde and bromonitromethane.  In
the aerobic aquatic system, benzaldehyde and bromonitromethane were
maximums of 0.297 µg/mL and 0.502 µg/mL at 2 hours, respectively, in
the water; and <0.307 µg/g and <0.189 µg/g at 1 day, respectively, in
the sediment.  In the anaerobic aquatic system, benzaldehyde and
bromonitromethane were maximums of <0.245 µg/mL and 0.382 µg/mL at 2
hours, respectively, in the water; and 6.94 µg/g and <0.187 µg/g at 2
hours, respectively, in the sediment.  These studies (MRID Nos.
409168-01 and 920110-17; and MRID Nos. 409169-01 and 920110-16) contain
several deviations from good scientific practices.  Therefore, these
aerobic aquatic (OPP 162-4) and anaerobic aquatic (OPP 162-3) metabolism
studies are considered useful supplemental information in fulfillment of
the aerobic and anaerobic aquatic metabolism guideline data requirements
for Bromonitrostyrene.  They provide useful supplemental information for
risk assessment.

In an adsorption/desorption study, α-carbon-labeled
[14C]Bromonitrostyrene (radiochemical purity ca. 96%) was determined to
be slightly mobile to moderately mobile in four domestic soils (silty
clay loam, silt loam, sandy loam soils and sand sediment).   Freundlich
adsorption Kd values were 4.56, 4.57, 8.99, and 13.5 for the silty clay
loam soil, silt loam soil, sandy loam soil and sand sediment,
respectively; corresponding Freundlich Koc values were 770, 1570, 1180,
and 853.  These studies (MRID Nos. 408177-01, 920110-18 and 459009-01)
contain several deviations from good scientific practices.  Therefore,
these adsorption/desorption (OPP 163-1) guideline studies are considered
useful supplemental information in fulfillment of the
adsorption/desorption guideline data requirements on the mobility (batch
equilibrium) of Bromonitrostyrene.  They provide useful supplemental
information for risk assessment.

A supplemental adsorption/desorption study was performed to determine
the Koc value for unlabeled Bromonitrostyrene (BIOBAN BNS; chemical
purity 99.7%) by comparing its retention time on an HPLC column.  The
column contained a stationary phase composed of cyanopropyl groups
bonded onto silica (OECD Method 121), and was compared to a series of
reference compounds that have an experimentally determined Koc.  The
determined Koc value for BIOBAN BNS using the HPLC method was 3.0.  This
value was in good agreement with the Koc values determined by two
different commercially available quantitative structure activity
relationship (QSAR) programs (3.0 and 2.7). This study (MRID 459009-01)
is considered supplemental information for the adsorption/desorption
guideline requirements (OPP 163-1).

 A supplemental soil column leaching study was performed using
α-carbon-labeled [14C]Bromonitrostyrene (radiochemical purity ca. 96%)
in four domestic unaged soils (two silty clay loam soils, a clay loam
soil and a silt loam soil) eluted with deionized water, then sawed into
1-inch sections.  No attempt was made to characterize the radioactivity
in any matrix; volatiles were not trapped.  Estimated desorption
coefficients indicated Bromonitrostyrene desorbed readily from all soil
types tested.  In the silty clay loam 1, silty clay loam 2, clay loam,
and silty loam, the Kd values were 30, 126, 23, and 17, respectively. 
This soil column leaching study (MRID Nos. 411916-01, 409309-01 and
920110-19) contains several deviations from good scientific practices,
and therefore is considered useful supplemental information in
fulfillment of the soil column leaching guideline data requirements (OPP
163-1) for Bromonitrostyrene and it provides useful supplemental
information for risk assessment.

	In a summary of a bioaccumulation in fish study (MRID No. None; EFED
Document No. 2020700), Bluegills were exposed to 0.05 ppm, 0.1 ppm, and
2 ppm of Bromonitrostyrene (labeling and purity not reported) for 30
days or 24 weeks.  No signs of distress or death were observed after 30
days of exposure to 0.05 ppm and 0.1 ppm of Bromonitrostyrene, and after
24 weeks of exposure to 2 ppm of Bromonitrostyrene.  This study
satisfies the bioaccumulation in fish data requirements for
Bromonitrostyrene (OPP 165-4).

II.	Environmental Fate Assessment (EPI Suite Summary)

	The Agency has used its databases (EPI Suite) to conduct the
environmental fate risk assessment.  EPI Suite estimates
physical/chemical properties, environmental fate and transport, and
includes estimation programs for Log Kow, Koc, Atmospheric Oxidation
Potential, Henry's Law Constant, Water Solubility, Melting Point,
Boiling Point, Vapor Pressure, Biodegradation, Bioconcentration Factor,
Hydrolysis, Sewage Treatment Plant Removal, Fugacity Modeling, and
Multimedia Modeling.

Bromonitrostyrene is not bioaccumlative (log Kow is 2.34) and poses a
low to moderate concern for bioconcentration in aquatic organisms due to
a bioconcentration factor (BCF) of 12.65.  Hydrolysis is expected to be
an important environmental fate process due to Bromonitrostyrene’s
instability against strong acids and bases.  Bromonitrostyrene is
immobile in soils based upon an estimated Koc value of 1,051.  However,
recently reviewed studies in four domestic soils indicate
Bromonitrostyrene adsorption Koc values of 770 to 1,570, which are
classified as slightly mobile to moderately mobile based on Standardized
Soil Mobility Classification Guidance (OPP/EFED Memorandum, April 21,
2006).  Bromonitrostyrene is not expected to volatize from dry soil
surfaces based upon an estimated vapor pressure of 6.76 x 10-4 mm Hg.
Bromonitrostyrene is confirmed to be non-biodegradable according to the
standard test of the Japanese Ministry of Industry and Trade (MITI). 
Its half-life in air is 37.99 hours (estimated), calculated from its
rate constant of 6.4820 x 10-12 cu cm/molecule-sec that was derived
using a structure estimation method.

Environmental Fate Assessment for Bromonitrostyrene based on EPI Suite:

Bromonitrostyrene (PC Code 101401) is registered as an active product
and is used primarily as a fungicide to control the growth of bacteria
and fungi in aqueous systems.  The following fate properties were
obtained from EPA internal environmental fate databases, open
literature, and from the Estimation Programs Interface (EPI) Suite: 

	

Vapor Pressure: 6.76 x 10-4 mm Hg at 25°C.

Henry law Constant (air/water partition coefficient): 6.93 x 10-7 atm-cu
m/mole at 25°C.

Koc (organic carbon ratio in soil): 770 to 1,570, slightly to moderately
mobile.

Log Kow (octanol/water partition coefficient): 2.34.

Bromonitrostyrene may be susceptible to direct photolysis; a direct
photolysis half-life of 1.70 hours has been measured.

Bromonitrostyrene is confirmed to be non-biodegradable according to the
standard test of the Japanese Ministry of Industry and Trade (MITI).

Water solubility is 127.4 mg/L at 25°C.

Vapor-phase Bromonitrostyrene is degraded in the atmosphere by reaction
with photochemically-produced hydroxyl radicals; its half-life in air is
37.99 hours (estimated).  

Sediment adsorption coefficient of 1,051, immobility in soil.

Log BCF: 1.102; BCF: 12.65 (EPI Suite summary).

Volatilization and bioconcentration are not expected to be significant
fate processes for bromonitrostyrene.  The Henry’s Law constant for
Bromonitrostyrene indicates that it is expected to be essentially
nonvolatile from water surfaces.  Bromonitrostyrene has a high
absorptivity and therefore is immobile in soil.  However, recently
reviewed studies in four domestic soils indicate Bromonitrostyrene
adsorption Koc values of 770 to 1,570, which are classified as slightly
mobile to moderately mobile based on Standardized Soil Mobility
Classification Guidance (OPP/EFED Memorandum, April 12, 2006). 
Bromonitrostyrene is confirmed to be non-biodegradable according to the
standard test of the Japanese Ministry of Industry and Trade (MITI). 
The log Kow (2.34) indicates that bioaccumulation in aquatic organisms
like fish is not likely.  With a vapor pressure of 6.76 x 10-4 mm Hg at
25°C Bromonitrostyrene is not expected to volatize from dry soil
surfaces.  The vapor phase will degrade by reaction with
photochemically-produced hydroxyl radicals (half-life of 37.99 hours).

Surface Water and Ground Water Contamination:

Bromonitrostyrene’s use as a wide-spectrum biocide, most frequently as
a fungicide to combat the formation of slime in paper and pulp mill
operations may result in its direct release to the environment. 
However, due to its reported instability and susceptibility to breakdown
by hydrolysis and ultraviolet light, it is unlikely to be a significant
environmental contaminant (Friend and Whitekettle, 1980).APPENDIX

Environmental Fate Data for Bromonitrostyrene

Bromonitrostyrene was registered with EPA on October 12, 1972.  The Dow
Chemical Company has submitted the required guideline studies for an
environmental fate assessment.  The Agency is using these environmental
fate studies for fate assessment of bromonitrostyrene to fulfill the
reregistration requirements.

Parameter	Value	Comment

Molecular weight	228.1 g/mol

	Molecular formula	C8H6BrNO2

	Water Solubility (g/100 mL) at 25(C.	0.001 	MRID Nos. 108467,

41603502, and 92011020

Other Solubility (g/100 mL) at 25(C.	95% Ethanol: 4

Acetone: 100

at 25˚C ± 0.5˚C	4.14 x 10-4 mm Hg 	MRID No. 42361405

pKa	Does not dissociate

	Kow/log Kow  SEQ CHAPTER \h \r 1 	Log Po/w = 2.34 (EPI Suite)

Log PBNS = 2.71 (Calculated value)	MRID Nos. 92011999

40661011

  SEQ CHAPTER \h \r 1 Stability of compound at room temperature	Stable
under normal storage conditions and in nonalcoholic solvents in the dark
or artificial light.	MRID Nos. 108467

41603502

92011020

A.	Environmental Fate Guideline Studies

	1.	Hydrolysis (OPP Guideline Number 161-1; MRID Nos. 423614-03,
423614-04 and 425385-01)

	The hydrolysis study was reviewed by the Agency and fulfills the
hydrolysis data requirements for Bromonitrostyrene.  Additionally,
several supplemental hydrolysis studies were submitted to the Agency.

The hydrolysis of α-carbon-labeled [14C]Bromonitrostyrene
[(2-bromo-2-nitroethenyl)-benzene, β-bromo-β-nitrostyrene,
2-bromo-2-nitrostyrene; radiochemical purity 98.0%, specific activity
240.8 μCi/mg], in acetonitrile, was studied in sterile pH 5 (acetate),
pH 7 (HEPES), pH 7 (TRIS), and pH 9 (borate) aqueous buffer solutions at
an application rate of 5 μg/mL (molarities of the buffer solutions was
not reported).  The test system consisted of sealed amber borosilicate
glass flasks which were incubated in the dark at 25 ± 1°C for 24
hours; volatiles were not collected.  Duplicate samples were taken for
analysis at 0, 0.5, 1, 2, 3, 4, 5, and 24 hours posttreatment.  The
buffer solutions were analyzed directly by liquid scintillation counting
(LSC) for total radioactivity.  A portion of the buffer solution was
acidified to pH 2 with 6N HCl and extracted three times with ethyl
acetate.  Quantification and identification of the
[14C]Bromonitrostyrene residues was performed by analyzing the ethyl
acetate extracts with HPLC.  Confirmation of the identifications was
performed via 1-D TLC of the 5-hour samples.

	Bromonitrostyrene hydrolyzed with half-lives of less than 24 hours in
sterile pH 5, pH 7 (HEPES and TRIS), and pH 9 buffer solutions incubated
in sealed amber borosilicate glass flasks at 25°C for 24 hours.  In the
pH 5 buffer solution, the parent was 107.8% of the applied at time 0,
then declined to 70.0% at 5 hours, and was 19.9% at 24 hours.  In the pH
7 HEPES buffer solution, the parent was 107.9% of the applied at time 0,
then declined to 69.2% at 5 hours, and was 7.4% at 24 hours.  In the pH
7 TRIS buffer solution, the parent was 95.8% of the applied at time 0,
then declined to 60.2% at 5 hours, and was 3.1% at 24 hours.  In the pH
9 buffer solution, the parent was 101.0% of the applied at time 0, then
declined to 65.5% at 3 hours, to 47.2% at 5 hours, and was 0.89% at 24
hours.  The half-lives for Bromonitrostyrene in pH 5, pH 7 (HEPES), pH 7
(TRIS), and pH 9 buffer solutions at 25°C were 10.32 hours, 6.17 hours,
4.68 hours and 3.40 hours, respectively.

	The major transformation product in all solutions was benzaldehyde,
which was present at maximums of 83.7%, 89.7%, 99.9% and 74.0% of the
applied at 24 hours posttreatment in the pH 5, pH 7 (HEPES), pH 7
(TRIS), and pH 9 buffer solutions, respectively. 
2-Bromo-2-nitro-1-phenyl ethanol (as a mixture of diastereomers;
degradate 1) was a major transformation product in the pH 5 buffer
solutions only.  In the pH 5 buffer solutions, 2-bromo-2-nitro-1-phenyl
ethanol was observed at a maximum of 11.8% at 3 hours, then declined to
2.6% at 24 hours.  In the pH 7 (HEPES), pH 7 (TRIS), and pH 9 buffer
solutions, 2-bromo-2-nitro-1-phenyl was maximums of 4.4%, 2.2% and 2.4%,
respectively.  Benzoyl formic acid (degradate 2) was a major
transformation product in the pH 9 buffer solutions only.  In the pH 9
buffer solutions, benzoyl formic acid was a maximum of 14.0% at 24
hours.  In the pH 5, pH 7 (HEPES), and pH 7 (TRIS) buffer solutions,
benzoyl formic acid was maximums of 2.6%, 4.0%, and 4.8%, respectively. 
An identified minor transformation product was benzoic acid, found at
maximums of 0.8%, 0.2%, 0.5%, and 0.3% in the pH 5, pH 7 (HEPES), pH 7
(TRIS) and pH 9 buffer solutions, respectively.  An unidentified minor
transformation product (degradate 3) was maximums of 0.2-4.0% in the
four buffer solutions.

	The overall recoveries ranged from 93.1-100.0% of the applied (96.9% ±
2.3%) in the pH 5 buffer solution, 89.1-100.0% (96.9% ± 3.4%) in the pH
7 (HEPES) buffer solution, 94.2-100.0% (97.5% ± 2.4%) in the pH 7
(TRIS) buffer solution and 92.9-100.0% (96.5% ± 2.3%) in the pH 9
buffer solution.  There was a pattern of loss of recovery over time in
all of the buffer solutions.

Supplemental Hydrolysis (OPP Guideline Number 161-1; MRID No.124516)

This study was reviewed by the Agency and was classified unacceptable,
but upgradeable, for the following reasons: pH was not stated or
controlled; the transformation products were not monitored; water was
not sterilized; temperature was room temperature; and mass balance was
not stated.  Therefore, this study is considered as supplemental
information for the hydrolysis of bromonitrostyrene.

In this study, the half-life of Bromonitrostyrene
[(2-bromo-2-nitroethenyl)-benzene, β-bromo-β-nitrostyrene,
2-bromo-2-nitrostyrene; labeling and purity not reported] was estimated
at 5.36 hours using UV detection (pH not stated or controlled).

b.  Supplemental Hydrolysis (MRID No. None; EFED Document No. 2020704)

This study was reviewed by the Agency; however, a classification was not
indicated.  Deficiencies include the following:  the temperature and
darkness under which this study was performed were not confirmed.

At pH 9, the half-life of Bromonitrostyrene applied at 10 ppm in water
was 5.3 hours; benzaldehyde and bromonitromethane were hydrolysis
products.

Supplemental Hydrolysis (OPP Guideline Number 161-1; MRID No. 124521)

This study was reviewed by the Agency and was classified unacceptable,
but upgradeable for the following reasons: the transformation products
were not monitored; water was not sterilized; temperature was room
temperature; and mass balance was not stated. Therefore, the study is
considered supplemental information for the hydrolysis of
bromonitrostyrene.

β-bromo-β-nitrostyrene, 2-bromo-2-nitrostyrene; labeling and purity
not reported] was applied at a rate of 10 ppm to distilled water and
Passaic river water at pH 5, 7, and 9 for up to 24 hours.  Samples at pH
5 and 7 were analyzed for the parent at 0, 1, 2, 3, 6, and 24 hours
posttreatment.  Samples at pH 9 were analyzed for the parent at 0, 0.5,
1, 3, 6, and 24 hours posttreatment.  In the distilled water, the rate
of hydrolysis was faster at pH 9 than at pH 7.  At pH 5,
Bromonitrostyrene decreased from 10 ppm at time 0, to 5 ppm at 6 hours,
to 0.5 ppm at 24 hours.  At pH 7, Bromonitrostyrene decreased from 10
ppm at time 0, to 4.3 ppm at 6 hours, to 0.5 ppm at 24 hours.  At pH 9,
Bromonitrostyrene decreased from 10 ppm at time 0, to 5.5 ppm at 1 hour,
to 3.6 ppm at 3 hours, to 0.5 ppm at 6 hours, and was not detected at 24
hours.  The same trend was observed in the river water, but the
degradation occurred faster in the river water than the distilled water.
 At pH 5, Bromonitrostyrene decreased from 10 ppm at time 0, to 6.1 ppm
at 3 hours, to 3.2 ppm at 6 hours, to 0.5 ppm at 24 hours.  At pH 7,
Bromonitrostyrene decreased from 10 ppm at time 0, to 4.3 ppm at 2
hours, to 0.5 ppm at 6 hours, and was not detected at 24 hours.  At pH
9, Bromonitrostyrene decreased from 10 ppm at time 0, to 2.4 ppm at 0.5
hours, to 0.5-0.7 ppm at 1-3 hours, and was not detected at 6-24 hours.
The transformation products were not monitored.  Hydrolysis was rapid;
however half-lives were not determined.

β-bromo-β-nitrostyrene, 2-bromo-2-nitrostyrene; labeling and purity
not reported] at a rate of 10 ppm was added to water buffered at pH 9. 
Samples were analyzed for BNS, benzaldehyde, and bromonitromethane (BNM)
at 1, 2, 2.7, 5, and 7 hours posttreatment.  BNS decreased from 8.9 ppm
at 1 hour, to 4.10 ppm at 7 hours.  Benzaldehyde increased from 0.3 ppm
at 1 hour, to 2.85 ppm at 7 hours.  BNM increased from 0 ppm at 1 hour,
to 3.65 ppm at 7 hours.  The total recoveries ranged 9.2 ppm to 10.6
ppm.  The two conclusions from this data were that degradation takes
place with rapid build-up of degradation products and that there is room
for error based on the total recoveries.

	2.	Photodegradation in Water (OPP Guideline No. 161-2; MRID Nos.
423614-01, 423614-02, and 425385-02)

	The photodegradation in water study was reviewed by the Agency and
classifed acceptable, fulfilling the photolysis in water data
requirements for Bromonitrostyrene.

	In the study, α-carbon-labeled [14C]Bromonitrostyrene
[(2-bromo-2-nitroethenyl)-benzene, β-bromo-β-nitrostyrene,
2-bromo-2-nitrostyrene; radiochemical purity 98.5%, specific activity
not reported] was added to a sterile pH 5 aqueous buffer solution at an
unreported rate (the identity and molarity of the buffer solution were
not reported).  The treated pH 5 buffer solutions were exposed to
artificial light (unreported light/dark cycles, unreported irradiation
source) for 12 hours.  A dark control was prepared and subjected to the
same experimental conditions, except that it was unexposed.  Sampling
intervals and analytical methods were not reported.  The calculated
half-lives for Bromonitrostyrene in the pH 5 solutions were 1.70 hours
in the exposed system and 10.4 hours in the unexposed system.  The
decline of the parent was not reported as percentage of the applied.

	Three major transformation products were identified:
2-phenyl-2-isonitroso acetic acid, benzaldehyde, and
2-bromo-2-nitro-1-phenyl ethanol.  2-Phenyl-2-isonitroso acetic acid was
only observed in the exposed system, increasing to a maximum of 36.6% of
the applied at 5 hours, then declining to 24.1% at 12 hours. 
Benzaldehyde was identified as a hydrolysis product, but was observed in
greater amounts in the exposed system.  Benzaldehyde was a maximum of
72.9% and 49.6% in the exposed samples and unexposed samples,
respectively.  2-Bromo-2-nitro-1-phenyl ethanol (as a mixture of
isomers) was present in both the exposed and unexposed systems with a
maximum of 15.8% at 1 hour.  One minor transformation product, benzoyl
formic acid, was a maximum of 6.5% at 1 hour in the exposed system only.
 Total recoveries were not reported.

	3.	Anaerobic Aquatic Metabolism (OPP Guideline No. 162-3; MRID Nos.
409169-01 and 920110-16)

This anaerobic aquatic metabolism study was reviewed by the Agency and
is considered useful supplemental information in fulfillment of the
anaerobic aquatic metabolism data requirements for Bromonitrostyrene. 
Several deviations from good scientific practices were noted:  the
material balances were <90%; the sampling intervals were inadequate to
accurately establish a half-life for the parent and transformation
products; anaerobic conditions prior to treatment and during the study
were not confirmed; the pattern of formation and decline of the
transformation products could not be determined; the methods may not
have been adequate to accurately characterize and quantify the parent
and transformation products.

	The anaerobic aquatic biotransformation of Bromonitrostyrene was
studied using subsamples (25 g dry weight) of sieved (2 mm) sediment
from Jacksonville, Florida (92.0% sand, 2.0% silt, 6.0% clay, pH 5.5,
organic matter 5.0%) flooded with 75 mL of river water from the same
site (pH 7.0).  The water:sediment ratio used was ca. 3:1 (75 mL
water:25 g dry wt. sediment).  The water-sediment samples were treated
with a sufficient amount of α-carbon-labeled [14C]Bromonitrostyrene
[(2-bromo-2-nitroethenyl)-benzene, β-bromo-β-nitrostyrene,
2-bromo-2-nitrostyrene, Giv 2-0820; radiochemical purity ca. 96%) to
achieve a nominal rate of 10.3 mg/L.  The test systems were incubated
under anaerobic (static, nitrogen atmosphere) conditions in darkness at
24.0 ( 1.1(C for 14 days.  Each 250-mL glass Erlenmeyer flask containing
treated water and sediment was connected to a volatile trapping system
consisting of ethylene glycol, 1.0M H2SO4 and 1.0M NaOH traps. 
Anaerobic conditions were maintained by flowing filtered, humidified
nitrogen through the sample flasks to the volatile traps.  Following
treatment, duplicate flasks were collected after 2 hours and 1, 2, 4, 7,
and 14 days of incubation.  Volatile traps were sampled at the same
intervals.  Sterilized test systems were also prepared as controls;
single flasks were collected after 2 hours, and 2 and 7 days of
incubation.

	At each sampling interval, sediment:water samples were filtered using
vacuum to separate the water layer from the sediment.  The water layer
was filtered again prior to liquid scintillation counting (LSC) and high
performance liquid chromatography (HPLC) analysis.  Prior to analysis by
gas chromatography (GC), water samples were extracted once using
dichloromethane; the dichloromethane extract was dried (sodium sulfate)
and analyzed by GC.  Aliquots of the sediment were used for moisture
determination prior to determination of total radioactivity by LSC
following combustion.  The filter paper was also subjected to
LSC/combustion.  The sediment was extracted once using acetonitrile;
acetonitrile extracts were analyzed by HPLC.  The trapping solutions
were analyzed using LSC.  Quantification and identification of the
[14C]Bromonitrostyrene residues was performed using HPLC and GC. 
However, the concentrations of [14C]Bromonitrostyrene residues were not
reported as a percent of applied, but as µg/mL in the water layer and
µg/g in the sediment.  Also, results were not reported for any sampling
interval after the first two sampling intervals for the nonsterile test
system; for the sterile test system, only results from the first
sampling interval were reported.

	The overall recovery of radiolabeled material averaged 57.87 ( 17.04%
of the applied (range 35.49-87.39%) in the total system, with no
discernable pattern of decline but a large variability between
replicates.  The overall recovery in the water increased from 16.2% at 2
hours to a maximum of 21.5% at 1 day, then declined to 12.6% at 4 days,
and to 3.2% at 14 days (range 3.1-22.5%).  The overall recovery in the
sediment increased from 25.6% at 2 hours, to a maximum of 67.8% at 4
days, then declined to a minimum of 11.8% at 7 days, before increasing
to 39.4% at 14 days, with large variability between replicates (range
9.0-68.5%).  The amounts of extractable and non-extractable residues
were not reported.  Volatiles reached a maximum of 21.4% at 14 days.

In the water layer, [14C]Bromonitrostyrene decreased from an average of
<0.225 (g/mL at 2 hours, to <0.14 (g/mL at 1 day.  In the sediment,
[14C]Bromonitrostyrene was <0.293 (g/g at 2 hours and <0.144 (g/g at 1
day.  The half-lives for Bromonitrostyrene were not calculated because
data were only provided for the first two sampling intervals (2 hours
and 1 day).  Two transformation products were identified: benzaldehyde
and bromonitromethane.  In the water layer, benzaldehyde accounted for
<0.245 (g/mL at 2 hour and <0.193 (g/mL at 1 day; in the sediment,
benzaldehyde accounted for 6.94 (g/g at 2 hours and <0.280 (g/g at 1
day.  Bromonitromethane accounted for 0.382 (g/mL at 2 hours and <0.232
(g/mL at 1 day in the water layer, and <0.187 (g/g at 2 hours and <0.180
(g/g at 1 day in the sediment layer.  The pathway of anaerobic
biotransformation of [14C]Bromonitrostyrene in the water-sediment system
was not described.

	The overall recovery of radiolabeled material for the sterile samples
averaged 76.34 ( 31.62% of the applied (range 50.19-111.48%) in the
total system.  The overall recovery in the water decreased from 50.5% at
2 hours, to 27.5% at 2 days, and was 22.1% at 7 days.  The overall
recovery in the sediment increased from 14.5% at 2 hours, to 17.9% at 2
days, to 65.9% at 7 days.  At 2 hours posttreatment, Bromonitrostyrene
was detected at <0.225 (g/mL in the water layer and at <0.247 (g/g in
the sediment.  The half-lives for bromonitrostyrene were not calculated
because data were only provided for the first sampling interval (2
hours).  Benzaldehyde was detected at <0.245 (g/mL in the water layer
and at 8.55 (g/g in the sediment.  Bromonitromethane was detected at
0.463 (g/mL in the water layer and at <0.176 (g/g in the sediment.

	4.	Aerobic Aquatic Metabolism (OPP Guideline No. 162-4; MRID Nos.
409168-01 and 920110-17)

This aerobic aquatic metabolism study was reviewed by the Agency and is
considered useful supplemental information in fulfillment of the aerobic
aquatic metabolism data requirements for Bromonitrostyrene.  Several
deviations from good scientific practices were noted:  the material
balances were <90%; the sampling intervals were inadequate to accurately
establish a half-life for the parent and transformation products;
aerobic conditions during the study were not confirmed; the pattern of
formation and decline of the transformation products could not be
determined; the methods may not have been adequate to accurately
characterize and quantify the parent and transformation products.

		The aerobic aquatic biotransformation of Bromonitrostyrene was studied
using subsamples (25 g dry weight) of sieved (2 mm) sediment from
Jacksonville, Florida (92.0% sand, 2.0% silt, 6.0% clay, pH 5.8, organic
carbon 2.9%) flooded with 75 mL of stream water from the same site (pH
7.0).   The sediment:water ratio was ca. 3:1 (25 g dry wt. sediment:75
mL water).  The water-sediment samples were treated with a sufficient
amount of α-carbon-labeled [14C]Bromonitrostyrene
[(2-bromo-2-nitroethenyl)-benzene, β-bromo-β-nitrostyrene,
2-bromo-2-nitrostyrene; radiochemical purity 96%) to achieve a nominal
rate of 10.0 mg/L. The test systems were incubated under aerobic
conditions for 14 days in darkness at 24.0 ( 1.1(C.  Each 250-mL glass
Erlenmeyer flask containing treated water and sediment was connected to
a volatile trapping system consisting of ethylene glycol, 1.0M H2SO4,
and 1.0M NaOH traps.  Aerobic conditions were maintained via filtered,
humidified air flowing through the sample flasks to the volatile traps. 
Following treatment, duplicate flasks were collected after 2 hours and
1, 2, 4, 7, and 14 days of incubation.  Volatile traps were sampled at
the same intervals.  Sterilized test systems were also prepared as
controls; single flasks were collected after 2 hours and 2 and 7 days of
incubation.

		At each sampling interval, sediment:water samples were filtered using
vacuum to separate the water layer from the sediment.  The water layer
was filtered again prior to liquid scintillation counting (LSC) and high
performance liquid chromatography (HPLC) analysis.  Prior to analysis by
gas chromatography (GC), water samples were extracted once using
dichloromethane; the dichloromethane extract was dried (sodium sulfate)
and analyzed by GC.  Aliquots of the sediment were used for moisture
determination prior to determination of total radioactivity by LSC
following combustion.  The filter paper was also subjected to
LSC/combustion.  The sediment was extracted once using acetonitrile;
acetonitrile extracts were analyzed by HPLC.  The trapping solutions
were analyzed using LSC.  Quantification and identification of the
[14C]Bromonitrostyrene residues was performed using HPLC and GC. 
However, the concentrations of [14C]Bromonitrostyrene residues were not
reported as a percent of applied, but as µg/mL in the water layer and
µg/g in the sediment.  Also, results were not reported for any sampling
interval after the first two sampling intervals for the nonsterile test
system; for the sterile test system, only results from the first
sampling interval were reported.

	The overall recovery of radiolabeled material averaged 73.05 ( 26.39%
of the applied (range 39.83-118.92%) in the total system, with no
discernable pattern of decline but a large variability between
replicates.  The overall recovery in the water decreased from an average
of 20.1% at 2 hours, to 8.2% at 1 day, to 1.9% at 14 days (range
1.6-23.3%).  The overall recovery in the sediment increased from an
average of 36.3-53.0% at 2 hours-1 day, to a maximum of 56.6% at 4 days,
and was 50.4% at 14 days, with a large variability between replicates
(range 22.4-83.5%).  The amounts of extractable and non-extractable
residues were not reported.  Volatiles reached a maximum of 31.6% at 14
days.

	In the water layer, Bromonitrostyrene decreased from 0.324 (g/mL at 2
hours, to <0.14 (g/mL at 1 day.  In the sediment, Bromonitrostyrene was
<0.205 (g/g to 0.415 (g/g at 2 hours and <0.151 (g/g to <0.164 (g/g at 1
day.  The half-lives for Bromonitrostyrene were not calculated because
data were only provided for the first two sampling intervals (2 hours
and 1 day).  Two transformation products were identified: benzaldehyde
and bromonitromethane.  Benzaldehyde accounted for <0.245 to 0.297 (g/mL
at 2 hour and <0.193 (g/mL at 1 day in the water layer and <0.275 (g/g
at 2 hours and <0.307 (g/g at 1 day in the sediment.  Bromonitromethane
accounted for 0.502 (g/mL at 2 hours and <0.232 (g/mL at 1 day in the
water layer, and <0.179 (g/g at 2 hours and <0.189 (g/g at 1 day in the
sediment.  An aerobic biotransformation pathway for
[14C]Bromonitrostyrene in the water-sediment system was not described.

		The overall recovery of radiolabeled material for the sterile samples
averaged 60.37 ( 12.61% of the applied (range 46.41-70.94%) in the total
system.  The overall recovery in the water decreased from 25% at 2 hours
to 14.4% at 2 days and was 10.2% at 7 days.  The overall recovery in the
sediment ranged from 44.3% at 2 hours, to 17.8% at 2 days, to 20.7% at 7
days.  At 2 hours posttreatment, Bromonitrostyrene was detected at 0.319
(g/mL in the water layer and at 5.31 (g/g in the sediment.  The
half-lives for Bromonitrostyrene were not calculated because data were
only provided for the first sampling interval (2 hours).  Benzaldehyde
was detected at 0.283 (g/mL in the water layer and at 0.423 (g/g in the
sediment.  Bromonitromethane was detected at 0.620 (g/mL in the water
layer and at <0.184 (g/g in the sediment. 

	5.	Adsorption/Desorption (OPP Guideline No. 163-1; MRID Nos. 408177-01,
920110-18, and 459009-01)

This adsorption/desorption study was reviewed by the Agency and is
considered useful supplemental information in fulfillment of the
adsorption/desorption data requirements on the mobility (batch
equilibrium) of Bromonitrostyrene.  Additional data are required on the
mobility of aged Bromonitrostyrene residues in soil.  Several deviations
from good scientific practices were noted:  the soils and sediment used
were autoclaved; the material balance was <90% of the applied; and the
transformation products were not identified or quantified.

The adsorption/desorption characteristics of the α-carbon-labeled
[14C]Bromonitrostyrene [(2-bromo-2-nitroethenyl)-benzene,
β-bromo-β-nitrostyrene, 2-bromo-2-nitrostyrene, GIV 2-0820;
radiochemical purity ca. 96%, specific activity 239 μCi/mg] was studied
a silty clay loam soil (pH 7.0, organic carbon 0.58%) from Mississippi,
a silt loam soil (pH 5.9, organic carbon 0.29%) from Arkansas, a sandy
loam soil (pH 4.9, organic carbon 0.76%) from California and a sand
sediment (pH 5.5, organic carbon 1.57%) from Massachusetts in a batch
equilibrium experiment.

Based on the results of preliminary batch equilibrium studies, an
equilibration period of 48 hours and soil:solution ratios of 1:5 (w:v;
Mississippi silty clay loam soil and Arkansas silt loam soil) and 1:20
(w:v; California sandy loam soil and Massachusetts sand sediment) were
chosen for this study.  For the adsorption phase of the study, aliquots
of 0.01M CaCl2 solution containing [14C]bromonitrostyrene at nominal
test concentrations of 0.2, 1.0, 5.0, and 20 mg a.i./kg soil
(Mississippi silty clay loam soil and Arkansas silt loam soil) and 0.8,
4.0, 20, and 80 mg a.i./kg soil (California sandy loam soil and
Massachusetts sand sediment) were added to subsamples (8.0 g or 11.0 g)
of each soil/sediment.  The soil/sediment samples had been air-dried via
autoclaving and sieved (2 mm) prior to the experiment.  Triplicate
samples were prepared for each soil type/treatment rate combination. 
After the adsorption equilibration period of 48 hours at 22.5 ( 3.5(C in
the dark, the soil:solution slurries were centrifuged; triplicate
aliquots of the supernatant were analyzed for total radioactivity by
liquid scintillation counting (LSC).

	The desorption phase of the study was carried out by replacing the
adsorption solution with an equivalent volume of 0.01M CaCl2 solution
and equilibrating in the dark at 21.9 ( 3.2(C for 48 hours.  Two
desorption steps were performed for each test soil.  Following
equilibration, the soil:solution slurries were centrifuged; triplicate
aliquots of the supernatant were analyzed for total radioactivity by
LSC.  The radioactivity in the soil residue after the second desorption
step was determined using LSC following combustion.

[14C]Bromonitrostyrene (GIV 2-0820) was determined to be mobile in silty
clay loam and silt loam soil:solution slurries (1:5) at nominal test
concentrations of 0.2-20 mg a.i./kg soil and in sandy loam soil and sand
sediment soil:solution slurries (1:20) at nominal test concentrations of
0.8-80 mg a.i./kg soil that were equilibrated in darkness at 22.5 (
3.5(C for 48 hours.   Freundlich adsorption K values were 4.56, 4.57,
8.99, and 13.5 for the Mississippi silty clay loam soil, Arkansas silt
loam soil, California sandy loam soil, and Massachusetts sand sediment,
respectively; corresponding Freundlich Koc values were 770, 1570, 1180,
and 853.  Registrant-calculated adsorption K and Koc values were not
reported.

Following the second desorption step, the percent of
[14C]bromonitrostyrene desorbed from the test soils, as percent of the
radioactivity adsorbed, was not determined.  Freundlich desorption K
values were 20.9, 22.7, 72.9, and 59.7 for the Mississippi silty clay
loam soil, Arkansas silt loam soil, California sandy loam soil, and
Massachusetts sand sediment, respectively; corresponding Freundlich
desorption Koc values were 3540, 7830, 9590, and 3750. 
Registrant-calculated desorption K and Koc values were not reported. 
Samples were not analyzed for transformation products.

Mass balances for soils at the end of the adsorption phase were not
reported.  Mass balances for soils at the end of the second desorption
step were 89.2 ( 10.4% (range 70.0-111.0%), 76.6 ( 9.7% (range
59.9-91.5%), 88.9 ( 5.4% (range 79.5-98.4%), and 77.0 ( 11.2% (range
58.6-88.8%) of the applied for the Mississippi silty clay loam soil,
Arkansas silt loam soil, California sandy loam soil, and Massachusetts
sand sediment, respectively.

	a.	Supplemental Adsorption/Desorption (OPP Guideline No. 163-1; MRID
Nos. 408177-01, 920110-18 and 459009-01)

This adsorption/desorption study was reviewed by the Agency and is
considered useful supplemental information in fulfillment of the
adsorption/desorption guideline data requirement for Bromonitrostyrene
by providing information on the Koc values for unlabeled
Bromonitrostyrene.

β-bromo-β-nitrostyrene, 2-bromo-2-nitrostyrene, BIOBAN BNS; chemical
purity 99.7%] and several other biocides were determined by comparing
their retention times on an HPLC column containing a stationary phase
composed of cyanopropyl groups bonded onto silica (OECD Method 121) to a
series of reference compounds which have an experimentally determined
Koc.  The standard method for determining the Koc value, which involves
a series of soils with varied organic carbon content, was not employed
because of the instability of Bromonitrostyrene in this system.  The
determined Koc value for BIOBAN BNS using the HPLC method was 3.0.  The
study authors also calculated the Koc values for the biocides using two
different commercially available quantitative structure activity
relationship (QSAR) programs, which were the QSAR programs from Syracuse
Research Corporation and ACD Labs.  For BIOBAN BNS, the Koc values
calculated by the QSAR programs from Syracuse Research Corporation and
ACD Labs were 3.0 and 2.7, respectively.  These were in good agreement
with the Koc value determined by the HPLC method.

	b.	Soil Column Leaching (OPP Guideline No. 163-1, MRID Nos. 411916-01,
409309-01, and 920110-19)

This soil column leaching study was reviewed by the Agency and is
considered useful supplemental information in fulfillment of the soil
column leaching guideline data requirements for Bromonitrostyrene. 
Several deviations from good scientific practices were noted:  the
material balances were <90% of the applied; transformation products were
not characterized; and none of the four soils tested had an organic
matter content <1%.

aged α-carbon-labeled [14C]Bromonitrostyrene
[(2-bromo-2-nitroethenyl)-benzene, β-bromo-β-nitrostyrene,
2-bromo-2-nitrostyrene; Giv 2-0820; radiochemical purity ca. 96%] was
investigated in two silty clay loam soils (silty clay loam 1: pH 7.3,
organic matter 4.4%; silty clay loam 2: pH 5.4, organic matter 3.9%)
from Illinois, a clay loam soil (pH 6.9, organic matter 1.3%) from
California, and a silt loam soil (pH 8.0, organic matter 1.4%) from
Texas.  Triplicate PVC columns (3-inch i.d. x 14-inch length) for each
test soil type were packed with 12 inches of sieved (2 mm), untreated
test soil, then saturated with deionized water.  [14C]Bromonitrostyrene
was applied to ca. 35 g (dry weight) of each soil at a rate of 10.0 mg
a.i./kg, and ca. 10 g of the treated soil was evenly distributed onto
the top of the corresponding soil column, resulting in a nominal rate of
0.1 mg a.i./column.  The soil columns were eluted with 2020 mL of
deionized water.  Aliquots of the total collected leachate were analyzed
directly by liquid scintillation counting (LSC).  The soil columns were
frozen and sawed into 1-inch sections; the top five sections were
analyzed by combustion/LSC.  No attempt was made to characterize the
radioactivity in any matrix.

The study author noted a true mass balance could not be reported because
degradation products were formed during the study due to hydrolysis of
bromonitrostyrene; however, transformation products were not identified.
 Radioactivity may have also been lost due to volatilization.  Estimated
desorption coefficients indicated bromonitrostyrene desorbed readily
from all soil types tested (Kd range 17-126).

For the Illinois silty clay loam 1, mass balances ranged from 42.6-45.4%
of the applied radioactivity.  Of the total radioactivity recovered,
85.9-93.9% remained in the 0-1 inch soil layer (mean of 88.8%, Section
1), with ≤0.8% detected in each of the 1-2, 2-3, 3-4, and 4-5 inch
segments (Sections 2 through 5).  Radioactivity in the leachate ranged
from 5.2-12.3% of the recovered (mean of 9.7%).  The estimated Kd value
was 30.

, 1.5-7.1% was detected in the 1-2 inch layer (mean of 3.5%, Section 2),
and ≤0.6% was in each of the 2-3, 3-4, and 4-5 inch segments (Sections
3 through 5).  Radioactivity in the leachate ranged from 9.2-15.0% of
the recovered (mean of 11.7%).  The estimated Kd value was 126.

ected in the 1-2 inch layer (mean of 6.5%, Section 2), and ≤1.4% was
in each of the 2-3, 3-4, and 4-5 inch segments (Sections 3 through 5). 
Radioactivity in the leachate ranged from 6.8-14.7% of the recovered
(mean of 11.7%).  The estimated Kd value was 23.

yer (mean of 1.9%, Section 2), and ≤0.6% was in each of the 2-3, 3-4,
and 4-5 inch segments (Sections 3 through 5).  Radioactivity in the
leachate ranged from 15.7-20.4% of the recovered (mean of 17.6%).  The
estimated Kd value was 17.

hI

# h*

h*

& h*

h*

 h*

h*

hå

h*

h*

h*

h*

h*

 h*

h*

# h*

h*

1$gdI

÷gd*

gd*

gd*

`„†ågd*

„° `„° gd*

gd*

gd*

$a$gd*

U

V

[

×

Ø

Ù

# h*

h*

 h*

h*

 h*

h*

  h*

h*

  h*

h*

# h*

h*

hI

hI

hI

5

U

V

…

¸

Ø

Ù

ó

$

%

0

2

L

]

n

|

~

´

µ

×

Ù

Ú

ë

@

gd*

&

@

`„ðñgd*

Ù

Ú

ì

í

@

h

h

h

h

h

h

h

h

yt

yt

yt

yt

yt

h

h

h

h

h

h

h

h

h

yt

yt

h;

h

e stock solution of unaged [14C]-labeled bromonitrostyrene
(radiochemical purity ca. 96%) was applied to the soil surface in each
biometer flask.  The soil was mixed, and the flasks were immediately
sealed and maintained in the dark for 2 days at 20-24°C.  The KOH
trapping solution was quantitatively removed and recharged on day 1.  On
days 1 and 2, aliquots of the KOH solution were analyzed using LSC. 
After 2 days, the soil and PUF plugs were removed from the flasks and
analyzed for total radioactivity using LSC following combustion.

After 2 days, material balances were 67.3% and 79.4% (mean 73.5%) of the
applied radioactivity for the duplicate test systems.  Of this,
45.9-56.8% of the applied was recovered from the soil, 21.3-22.4% from
the KOH trapping solution, and 0.1-0.2% from the PUF plugs.  Based on
these results, the study author concluded that the loss of radioactivity
in the soil column leaching study was caused by volatilization of
bromonitrostyrene and/or its biodegradation products.

	6.	Bioaccumulation in Fish (OPP Guideline No. 165-4; MRID No. None;
EFED Document No.  2020700)

	This bioaccumulation in fish study was reviewed by the Agency and
fulfills the bioaccumulation in fish data requirements for
Bromonitrostyrene.

	In this study, Bluegills were exposed to 0.05 ppm, 0.1 ppm, and 2 ppm
of Bromonitrostyrene for 30 days or 24 weeks.  No signs of distress or
death were observed after 30 days of exposure to 0.05 ppm and 0.1 ppm of
Bromonitrostyrene and after 24 weeks of exposure to 2 ppm of
Bromonitrostyrene.

Data Gap Table:  See Table below.

Environmental Fate Data Requirements for Bromonitrostyrene

OPP Guideline	Data

 Requirement	MRID

No.	Data Requirement

 Status

161-1	

Hydrolysis

(Required)

	

423614-03

423614-04

425385-01

124516

124521

	

Satisfied

161-2	

Photodegradation in Water (Required)

	

423614-01 

423614-02 

425385-02

	

Satisfied

162-3

	

Anaerobic Aquatic Metabolism (Required)

	

409169-01

920110-16	

Supplemental

162-4

	

Aerobic Aquatic Metabolism (Required)

	

409168-01

920110-17	

Supplemental

163-1	

Adsorption/Desorption (Required)	

408177-01

920110-18

459009-01

	

Supplemental

163-1	

Soil  Column Leaching

 (Not Required)

	

411916-01

409309-01

920110-19

	

Supplemental

165-4	

Accumulation Studies in Fish (Conditionally Required)	

MRID No.: None.

(EFED Document No. 2020700)

	

Satisfied

BIBLIOGRAPHY

161-1       Hydrolysis

124516	Porcaro, P.; Shubiak, P. (1972) Analyses of
Beta-bromo-beta-nitro- styrene and It's Hydrolysis Products.
(Unpublished study received Dec 21, 1972 under 824-8; submitted by
Givaudan, Clifton, NJ; CDL:004462-A) 

124521	Brandman, H. (1971) Hydrolysis of Giv-Gard BNS at Various pH's.
(Unpublished study received Dec 21, 1972 under 824-8; submitted by
Givaudan, Clifton, NJ; CDL:101505-C) 

42361403	Williamson, K.; Williams, M. (1992) Hydrolysis of BNS as a
Function of pH at 25(degree)C: Final Report: Lab Project Number: 40044.
Unpublished study prepared by ABC Laboratories, Inc. 78 p. 

42361404	Williamson, K.; Williams, M. (1992) Hydrolysis of ?carbon
14|-BNS as a Function of pH at 25(degree)C: Final Report: Lab Project
Number: 40044R. Unpublished study prepared by ABC Laboratories, Inc.
1484 p. 

42538501	Williams, M.; Bashir, M. (1992) Hydrolysis of BNS as a Function
of pH at 25 degrees celsius--Supplemental Report: Lab Project Number:
400441. Unpublished study prepared by ABC Labs, Inc. 30 p. 

161-2       Photodegradation-water

42361401	Williamson, K.; Williams, M. (1992) Determination of the
Aqueous Photolysis Rate of BNS: Final Report: Lab Project Number: 40045.
Unpublished study prepared by ABC Laboratories, Inc. 57 p. 

42361402	Williamson, K.; Williams, M. (1992) Determination of the
Aqueous Photolysis Rate of BNS: Final Report: Lab Project Number:
40045R. Unpublished study prepared by ABC Laboratories, Inc. 733 p. 

42538502	Williams, M.; Bashir, M. (1992) Determination of the Aqueous
Photolysis Rate of BNS--Supplemental Report: Lab Project Number: 400451.
Unpublished study prepared by ABC Labs, Inc. 29 p. 

162-3       Anaerobic aquatic metabolism

40916901	Martinson, J. (1988) Determination of the Biodegradability of
GIV 2-0820 in Soil and Water under Anaerobic Conditions: SLS Report:
88-11-2866: Study No.: 11629-0787-6103. Unpublished study pre- pared by
Springborn Life Sciences, Inc. 115 p. 

92011016	Lewis, B.; Manowitz, M. (1990) Givaudan Phase 3 Summary of MRID
40916901. Determination of the Biodegradability of Giv 2-0820 in Soil
and Water under Anaerobic Conditions: Project No. 88-11-2866. Prepared
by SPRINGBORN LIFE SCIENCES, INC. 17 p 

162-4       Aerobic aquatic metabolism

40916801	Martinson, J. (1988) Determination of the Biodegradability of
GIV 2-0820 in Soil and Water under Aerobic Conditions: Final Report: SLS
Report: 88-11-2865: Study No.: 11629-0787-6103. Unpublished study
prepared by Springborn Life Sciences, Inc. 114 p. 

92011017	Lewis, B.; Manowitz, M. (1990) Givaudan Phase 3 Summary of MRID
40916801. Determination of the Biodegradability of Giv 2-0820 in Soil
and Water under Aerobic Conditions: Project No. 88-11-2865. Prepared by
SPRINGBORN LIFE SCIENCES, INC. 14 p. 

163-1       Leaching/Adsorption/Desorption

40817701	Martinson, J. (1988) Determination of Adsorption and Desorption
Coefficients of Giv 2-0820: SLS Report #88-06-2753: Study #11629-6101.
Unpublished study prepared by Springborn Life Sciences, Inc. 68 p. 

40930901	Martinson, J. (1988) Mobility in Soils of GIV 2-0820 by the
Soil Column Leaching Method: Final Report: SLS Report #88-10-2838:
Laboratory Study No.: 11629-0787-6102. Unpublished study prepared by
Springborn Life Sciences, Inc. 35 p. 

41191601	Martinson, J. (1988) Mobility in Soils of GIV 2-0820 by the
Soil Column Leaching Method: Rev. Final Report: SLS Report #88-10- 2838.
Unpublished study prepared by Springborn Life Sciences, Inc. 45 p. 

45900901	Gonsior, S.; Rivard, M.; Stock, M. (2002) Estimating the Soil
Adsorption Coefficient (Koc) for a Series of Biocides by HPLC Using OECD
Method 121: Lab Project Number: STUDY 011094: 011094: 121. Unpublished
study prepared by The Dow Chemical Company. 41 p.

92011018	Lewis, B.; Manowitz, M. (1990) Givaudan Phase 3 Summary of MRID
40817701. Determination of Adsorption and Desorption Coefficients of Giv
2-0820: Project No. 88-06-2753. Prepared by SPRINGBORN LIFE SCIENCES,
INC. 12 p. 

92011019	Lewis, B.; Manowitz, M. (1990) Givaudan Phase 3 Summary of MRID
41191601. Mobility in Soils of Giv 2-0820 by the Soil Column Leaching
Method: Project No. 88-10-2838. Prepared by SPRINGBORN LIFE SCIENCES,
INC. 14 p. 

165-4       Bioaccumulation in Fish

None

	Givaudan Corp (1973) Evaluation of Environmental Data for
B-Bromo-B-nitrostyrene.  Reg. No. 824-8.  Unpublished study prepared by
Givaudan Corp. EFED Document No. 2020700.

Non-Guideline Documents

None	Friend, P.L. and Whitekettle, W.K. (1980).  Biocides and Water
Cooling Towers.  Dev. Ind. Microbiol. 21, 123-131.

None	The Estimation Programs Interface (EPI) Suite.  Windows based suite
of physical/chemical properties and environmental estimation models
developed by the US EPA’s Office of Prevention, Pesticides and Toxic
substances (OPPTS) and Syracuse Research Institute (SRC).  Physical
properties of Bromonitrostyren.  EPI Suite Summary (v3.12).   HYPERLINK
"http://www.epa.gov/opptintr/exposure/docs/EPISuitedl.htm"
http://www.epa.gov/opptintr/exposure/docs/EPISuitedl.htm 

None	Guidance document: Standard Soil Mobility Classification Guidance
dated April 21, 2006, by Roxolana Kashuba, Dana Spatz, and Steven
Bradbury, Fate and Transport Technology Team, Environmental Fate and
Effects Division, Office of Pesticide Program.

Sign-off Date: 02/22/07   DP Barcode No.:  D336286   

	  PAGE  1  of   NUMPAGES  24 	

C

Br

C

H

N

O

2