Document ID: EPA-HQ-OPP-2006-0339-0008
Agency: epa
Document Type: Supporting & Related Material
Title: 
Posted Date: 2006-04-26T04:00Z

UNITED
STATES
ENVIRONMENTAL
PROTECTION
AGENCY
WASHINGTON,
D.
C.
20460
OFFICE
OF
PREVENTION,
PESTICIDES
AND
TOXIC
SUBSTANCES
April
13,
2006
MEMORANDUM
SUBJECT:
Environmental
Fate
Assessment
of
Alkyl*
dimethyl
benzyl
ammonium
chloride
*(
50%
C14,
40%
C12,
10%
C16)
(
ADBAC)
for
the
Reregistration
Eligibility
Decision
(
RED)
Document
Case
No.:
0350­
26186
DP
Barcode:
322870
FROM:
Srinivas
Gowda,
Microbiologist/
Chemist
Risk
Assessment
and
Science
Support
Branch
(
RASSB)
Antimicrobials
Division
(
7510C)

TO:
Mark
Hartman,
Branch
Chief
Benjamin
Chambliss,
Team
Leader
Najm
Shamim,
Risk
Assessor
Regulatory
Management
Branch
II
Antimicrobials
Division
(
7510C)

Jacqueline
McFarland,
Chemical
Review
Manager
Regulatory
Management
Branch
I
Antimicrobials
Division
(
7510C)

THRU:
Siroos
Mostaghimi,
Acting
Team
Leader,
Team
one
Risk
Assessment
and
Science
Support
Branch
(
RASSB)
Antimicrobials
Division
(
7510C)

Norman
Cook,
Branch
Chief
Risk
Assessment
and
Science
Support
Branch
(
RASSB)
Antimicrobials
Division
(
7510C)

Chemical
Name
PC
Code
CAS#
Common
Name
Alkyl*
dimethyl
benzyl
ammonium
chloride
069105
68424­
85­
1
ADBAC
*(
50%
C14,
40%
C12,
10%
C16)

Environmental
Fate
Science
Chapter
and
Fate
Assessment
on
ADBAC
is
submitted
for
Reregistration
Eligibility
Decision
(
RED).
Page
2
of
14
ALKYL
DIMETHYL
BENZYL
AMMONIUM
CHLORIDE
(
ADBAC)
ENVIRONMENTAL
FATE
SCIENCE
CHAPTER
EXECUTIVE
SUMMARY
ADBAC
is
used
primarily
as
a
disinfectant,
a
sanitizer,
or
as
a
microbicide/
microbiostat.
It
also
serves
as
an
algaecide,
bactericide/
bacteriostat,
fungicide/
fungistat,
insecticide,
miticide,
virucide,
defoliant,
feeding
depressant,
repellent
and
tuberculocide.
Use
sites
for
ADBAC
include
agricultural
premises
and
equipment,
food
handling,
commercial,
industrial
and
institutional
settings,
residential
areas
or
areas
of
public
access,
pets
and
kennels,
medical
facilities,
swimming
pools,
aquatic
areas,
and
industrial
water
systems.
ADBAC
is
also
used
as
a
wood
preservative.
As
an
agricultural
pesticide,
ADBAC
is
used
for
ornamental
plants,
shrubs,
and
vines.
Some
of
the
required
guideline
studies
for
an
environmental
fate
assessment
have
been
submitted.
The
Agency
is
using
the
available
environmental
fate
studies
for
fate
assessment
of
ADBAC
to
fulfill
the
reregistration
requirements.
Because
of
its
use
as
a
wood
preservative,
an
aqueous
availability
study
evaluating
the
leachability
of
ADBAC
from
treated
wood
is
required.
However,
no
data
have
been
submitted
to
the
Agency.

ADBAC
is
hydrolytically
stable
under
abiotic
and
buffered
conditions
over
the
pH
5­
9
range.
ADBAC
is
also
stable
to
photodegradation
in
pH
7
buffered
aqueous
solutions.
However,
in
the
presence
of
a
photosensitizer
(
e.
g.,
acetone),
ADBAC
has
been
shown
to
degrade
with
an
estimated
half­
life
of
7.1
days.

Aquatic
metabolism
studies
under
aerobic
and
anaerobic
conditions
indicate
that
ADBAC
is
stable
to
microbial
degradation.
ADBAC
did
not
degrade
in
flooded
sand
loam
soil
that
was
incubated
at
24­
27
E
C
in
the
dark
for
up
to
30
days
in
an
aerobic
aquatic
metabolism
study.
Under
anaerobic
conditions,
ADBAC
was
found
to
be
very
resistant
to
degradation
with
a
calculated
half­
life
of
1,815
days.
However,
a
report
on
the
biodegradability
of
ADBAC
prepared
by
the
Registrant
concluded
that
the
degree
of
ADBAC
biodegradability
is
variable
and
is
influenced
by
the
chemical
concentration,
alkyl
chain
length,
the
presence
of
anionic
moieties
and
the
quantity
and
characteristics
of
the
microbial
population.
According
to
this
report,
ADBAC
is
biodegradable
and
environmentally
acceptable.
This
report
was
based
on
information
from
the
open
literature,
unpublished
sources,
and
meeting
proceedings
and
has
not
been
reviewed
by
the
Agency.

ADBAC
is
immobile
in
soil.
The
available
soil
mobility
study
shows
that
ADBAC
has
a
strong
tendency
to
bind
to
sediment/
soil
with
Freundlich
Kads
values
were
6,172
for
the
sand
soil,
10,797
for
the
silt
loam,
5,123
for
the
sandy
loam
soil,
and
32,429
for
the
clay
loam
and
the
corresponding
Koc
values
were
6,171,657
for
the
sand
soil,
2,159,346
for
the
silt
loam,
640,389
for
the
sandy
loam
soil,
and
1,663,039
for
the
clay
loam.
Because
of
its
strong
adsorption
to
soils,
ADBAC
is
not
expected
to
contaminate
surface
and
ground
waters.

Bioaccumulation
of
ADBAC
in
freshwater
fish
is
not
likely
to
occur.
Maximum
bioconcentration
factors
(
BCF)
were
33X
for
edible
tissues
(
muscle,
skin),
160X
for
nonedible
Page
3
of
14
tissues
(
viscera,
head,
carcass),
and
79X
for
whole
fish
tissues.
ADBAC
is
not
expected
to
pose
a
concern
for
bioconcentration
in
aquatic
organisms.

I.
Environmental
Fate
Assessment
A.
Abiotic
In
a
hydrolysis
study
conducted
under
abiotic
and
buffered
conditions,
alkyl
dimethyl
benzyl
ammonium
chloride
(
ADBAC),
did
not
hydrolyze
at
pH
9
(
estimated
half­
life
=
379
days)
and
appeared
hydrolytically
stable
at
pH
5
and
7
(
estimated
half­
lives
=
150­
183
days).
The
study
was
conducted
at
25
±
1
E
C
for
up
to
30
days.
The
hydrolysis
data
requirements
(
OPP
161­
1)
for
ADBAC
have
been
fulfilled
by
this
study
(
MRID
408356­
02).

The
photodegradation
potential
of
ADBAC
was
investigated
in
sensitized
and
nonsensitized
buffer
solutions
adjusted
to
pH
7
[
0.2
M
tris(
hydroxyl
methyl)
amino
methane].
ADBAC
did
not
degrade
in
the
pH
7
sterile
buffered
aqueous
solution
that
was
continuously
irradiated
over
a
30­
day
period
at
25
E
C.
In
contrast,
ADBAC
degraded
with
an
estimated
halflife
of
7.1
days
in
a
similar
buffer
solution
that
had
been
sensitized
with
1%
acetone.
ADBAC
did
not
degrade
in
the
dark
controls
of
the
sensitized
and
non­
sensitized
solutions.
An
unidentified
degradate,
isolated
from
the
sensitized
irradiated
solution
30­
days
post
treatment,
accounted
for
74.5%
of
the
applied
radioactivity.
Because
of
missing
information,
the
photodegradation
in
water
guideline
requirements
(
OPP
161­
2)
have
not
been
fulfilled
by
this
study
(
MRID
No.
408356­
03).

B.
Biotic
In
a
study
on
an
aerobic
aquatic
system,
ADBAC
did
not
degrade
in
flooded
sand
loam
soil
that
was
incubated
at
24­
27
E
C
in
the
dark
for
up
to
30
days.
During
the
study,
most
of
the
applied
radioactivity,
of
which
>
90%
was
extractable,
was
observed
in
the
soil
fraction.
The
aerobic
aquatic
metabolism
guideline
requirements
(
OPP
162­
4)
have
been
fulfilled
by
this
study
(
MRID
408356­
04).

Under
anaerobic
conditions,
ADBAC
was
found
to
be
very
resistant
to
degradation
in
flooded
sandy
loam
soil
that
had
been
incubated
for
a
year
at
25
E
C.
The
registrant­
calculated
half­
life
was
1,815
days.
No
degradation
products
were
found.
This
study
satisfies
the
anaerobic
aquatic
metabolism
guideline
requirements
(
OPP
162­
3)
(
MRID
Nos.
411055­
01
&
424151­
01).

A
review
of
information
from
the
open
literature,
unpublished
sources
and
meeting
proceedings
prepared
by
the
Registrant
indicates
that
ADBAC
is
readily
and
ultimately
degradable.
The
report
author
noted
that
the
aerobic
and
anaerobic
aquatic
metabolism
studies
for
ADBAC
were
designed
to
assess
environmental
fate
of
ADBAC
based
on
outdoor
applications
of
agricultural
chemicals,
but
not
the
direct
biodegradability
potential
of
this
chemical
as
a
result
of
its
use
as
an
antimicrobial.
Other
limitations
of
the
tests
were
noted,
such
as
loss
of
microbial
activity
during
air
drying
of
soil
material
and
limited
gas
exchange
in
the
Page
4
of
14
aerobic
test.
According
to
this
report,
the
degree
of
ADBAC's
biodegradability
is
variable
and
is
influenced
by
the
chemical
concentration,
alkyl
chain
length,
the
presence
of
anionic
moieties
and
the
quantity
and
characteristics
of
the
microbial
population.
A
mechanism
of
biodegradation
for
ADBAC,
in
which
several
bacterial
species
are
needed
for
ultimate
biodegradation
of
this
compound,
is
also
described.

The
adsorption/
desorption
characteristics
of
ADBAC
were
studied
on
four
representative
agricultural
soils:
sand,
sandy
loam,
silt
loam,
and
clay
loam.
The
study
determined
ADBAC
to
be
immobile
in
all
soils
tested.
Freundlich
Kads
values
were
6,172
for
the
sand
soil,
10,797
for
the
silt
loam,
5,123
for
the
sandy
loam
soil,
and
32,429
for
the
clay
loam
and
the
corresponding
Koc
values
were
6,171,657
for
the
sand
soil,
2,159,346
for
the
silt
loam,
640,389
for
the
sandy
loam
soil,
and
1,663,039
for
the
clay
loam.
Following
the
first
desorption
step,
Freundlich
Kdes
values
were
7,137
for
the
sand
soil,
14,083
for
the
silt
loam
soil,
96,540
for
the
sandy
loam
soil,
and
165,556
for
the
clay
loam
soil;
corresponding
Koc
values
were
7,137,310
for
the
sand
soil,
2,816,590
for
the
silt
loam
soil,
12,067,457
for
the
sandy
loam
soil,
and
8,490,062
for
the
clay
loam
soil.
Since
the
study
only
provides
information
on
the
mobility
of
unaged
ADBAC,
the
adsorption/
desorption
guideline
requirements
(
OPP
163­
1)
have
been
partially
fulfilled
(
MRID
Nos.
408356­
05
&
424148­
01).

A
study
consisting
of
a
35­
day
bioconcentration
and
a
21­
day
depuration
period
was
conducted
to
evaluate
the
bioconcentration
of
ADBAC
in
bluegill
sunfish
under
flow­
through
aquarium
conditions.
Analysis
of
edible
tissues
(
muscle,
skin),
whole
fish,
and
nonedible
tissues
(
viscera,
carcass)
were
performed
throughout
the
exposure
period.
Maximum
bioconcentration
factors
(
BCFs),
based
on
total
radioactivity,
were
33X
for
edible
tissues,
79X
for
whole
fish
tissues
and160X
for
nonedible
tissues.
The
maximum
concentrations
of
residues
occurred
at
day
35
and
were
3.4,
6.6,
and
13
ppm
for
edible
tissues,
whole
fish,
and
nonedible
tissues,
respectively.
After
21
days
of
depuration,
14[
C]
residues
were
2.4
ppm
in
edible
tissues,
3.7
ppm
in
whole
fish
tissues,
and
5.3
ppm
in
nonedible
tissues.
14[
C]
residues
in
edible
tissues
did
not
decline
significantly
from
the
concentrations
detected
during
the
exposure
period.
The
study
is
scientifically
valid,
but
it
does
not
satisfy
the
guidelines
(
OPP
165­
4)
for
bioaccumulation
in
fish
(
MRID
410268­
01)
since
residues
present
at
0.05
ppm
or
greater
in
the
treated
water
and
fish
were
not
identified.
Page
5
of
14
APPENDIX
Environmental
Fate
Data
for
ADBAC
A.
Environmental
Fate
Guideline
Studies
1.
Hydrolysis
(
OPP
Guideline
Number
161­
1,
MRID
No.
408356­
02)

This
study
was
reviewed
by
the
Agency
and
found
to
be
scientifically
valid.
The
hydrolysis
data
requirements
for
ADBAC
have
been
fulfilled.

Uniformly
ring­
labeled
[
14C]
ADBAC
(
alkyl
dimethyl
benzyl
ammonium
chloride;
radiochemical
purity
98%;
specific
activity
2.03
x
104
dpm/
µ
g),
diluted
with
nonradiolabeled
ADBAC
and
deionized
water,
was
added
at
1,298
µ
g/
flask
to
sterile
pH
5
(
acetic
acid),
pH
7
[
N­
2­
hydroxyethyl­
piperazine­
N'­
2­
ethanesulfonic
acid
(
HEPES)],
pH
7
[
tris(
hydroxymethyl)
aminomethane­
(
TRIS)]
and
pH
9
(
boric
acid)
aqueous
buffer
solutions.
Acetonitrile
was
added
to
the
buffer
solutions
as
a
cosolvent
at
<
1%.
The
final
nominal
concentration
of
[
14C]
ADBAC
in
the
treated
solutions
was
9.7
µ
g/
ml.
Aliquots
of
the
treated
buffer
solutions
were
added
to
amber­
colored
silanized
vials.
The
vials
were
capped
and
incubated
in
the
dark
at
25
±
1
E
C
for
30
days.
Duplicate
samples
were
collected
at
0,
1,
3,
7,
14,
22
and
30
days
post
treatment.

At
each
sampling
interval,
duplicate
aliquots
of
the
buffer
solutions
were
analyzed
for
total
radioactivity
by
liquid
scintillation
counting
(
LSC).
Sample
solutions
were
also
analyzed
for
specific
[
14C]
compounds
by
one­
dimensional
TLC
on
silica
gel
plates
developed
in
a
chloroform:
methanol:
formic
acid
(
60:
40:
2,
v:
v)
solvent
system.
A
radioscanner
was
used
to
locate
radioactive
areas
on
the
plates.
Autoradiographs
were
prepared
from
the
0­
and
30­
day
TLC
plates.
After
scrapping
radioactive
areas
from
the
plates,
the
radioactivity
was
desorbed
and
quantified
by
LSC.
The
pH
of
each
solution
was
also
measured
at
each
sampling
interval.

Uniformly
ring­
labeled
[
14C]
ADBAC,
at
a
nominal
concentration
of
9.7
µ
g
/
ml,
was
relatively
stable
to
hydrolysis
in
pH
5
and
7
buffer
solutions
(
half­
lives
were
150­
183
days),
decreasing
by
 
2.3%
of
the
recovered
radioactivity
during
30
days
of
incubation.
[
14C]
ADBAC
did
not
hydrolyze
in
pH
9
buffer
solution;
the
half­
life
was
calculated
to
be
379
days.

In
the
buffer
solutions,
the
parent
was
present
at
89.5
 
92.8%
of
the
applied
radioactivity
at
30
days
post
treatment.
The
original
containers
for
all
individual
samples
with
less
than
90%
recovery
were
further
extracted
with
methanol.
The
30­
day
mass
balance
increased
to
92.2­
97.4%
of
the
applied
radioactivity
when
the
methanol
rinse
of
the
vials
was
analyzed.
The
pH
of
all
buffer
solutions
remained
stable
throughout
the
study
period.

2.
Photodegradation
in
Water
(
OPP
Guideline
No.
161­
2,
MRID
No.
408356­
03)

This
photodegradation
study
was
reviewed
by
the
Agency
and
found
scientifically
valid.
However,
in
its
original
review
the
Agency
concluded
that
the
study
did
not
meet
guideline
Page
6
of
14
requirements
since
information
on
characterization
of
the
light
source
was
not
reported
and
one
[
14C]
compound
isolated
30
days
post
treatment
from
the
sensitized
irradiated
solution
at
74.5%
(
6.97
ppm)
of
the
applied
radioactivity
was
not
identified.
Supplemental
information
(
MRID
424152­
01)
submitted
by
the
Registrant
provided
information
on
the
light
source;
however,
the
identity
of
the
degradate
was
not
reported.
The
Agency
noted
that
there
are
many
organic
photosensitizers
in
the
environment,
so
it
is
important
to
identify
the
major
photoproduct
that
was
detected
in
the
photosensitized
system
(
EFGB,
1993).
The
photodegradation
in
water
guideline
requirements
for
ADBAC
have
not
been
fulfilled.
This
study
is
classified
as
upgradable.

In
this
study,
ring­
labeled
[
14C]
ADBAC
(
alkyl
dimethyl
benzyl
ammonium
chloride;
radiochemical
purity
98%;
specific
activity
2.03
x
104
dpm/
µ
g),
diluted
with
nonradiolabeled
ADBAC
and
deionized
water,
was
added
to
two
flasks
containing
sterile
pH
7
buffer
solution
(
tris(
hydroxy
methyl)
amino
methane)
prepared
with
<
1%
acetonitrile
as
cosolvent.
The
solution
in
one
flask
was
photosensitized
with
1%
acetone
(
v:
v).
Final
concentrations
of
[
14C]
ADBAC
were
9.11
ppm
and
9.35
ppm
in
the
nonsensitized
solution
and
sensitized
solution,
respectively.

Aliquots
of
the
treated
solutions
were
transferred
to
capped
culture
tubes.
Half
of
the
vials
containing
each
solution
were
covered
with
aluminum
foil
and
stored
inside
a
closed
box
(
dark
control
solutions).
The
box
was
placed
along
with
the
unwrapped
vials
in
a
photolysis
apparatus.
A
xenon
lamp,
characterized
as
having
approximately
one­
half
the
intensity
of
sunlight,
was
used
to
irradiate
the
samples.
The
temperature
in
the
photolysis
chamber
was
maintained
at
25
±
1
E
C.
Duplicate
samples
of
irradiated
and
dark
control
solutions
were
removed
for
analysis
at
approximately
0,
1,
3,
7,
10,
14,
21,
and
30
days
post
treatment.

At
each
sampling
interval,
duplicate
samples
of
irradiated
and
dark
control
solutions
were
analyzed
without
extraction
for
total
radioactivity
by
liquid
scintillation
counting
(
LSC).
The
aliquots
were
also
analyzed
for
specific
[
14C]
compounds
using
one­
dimensional
TLC
on
silica
gel
plates
developed
in
a
chloroform:
methanol:
formic
acid
(
60:
40:
2,
v:
v)
solvent
system.
A
radioscanner
was
used
to
locate
radioactive
areas
on
the
plates.
In
addition,
autoradiographs
were
prepared
from
the
0­
and
30­
day
TLC
plates.
After
scrapping
radioactive
areas
from
the
plates,
the
radioactivity
was
desorbed
and
quantified
by
LSC.
The
pH
of
each
solution
was
measured
at
each
sampling
interval.
The
volatilization
of
[
14C]
residues
from
the
irradiated
and
dark
control
samples
was
also
measured
by
analyzing
the
trapping
solutions
at
0,
1,
3,
7,
10,
14,
21,
and
30
days
post
treatment
for
total
radioactivity
using
LSC.

Ring­
labeled
[
14C]
ADBAC
(
alkyl
dimethyl
benzyl
ammonium
chloride;
radiochemical
purity
98%;
specific
activity
2.03
x
104
dpm/
µ
g),
at
approximately
9
ppm,
did
not
degrade
in
a
sterile
buffer
solution
that
was
irradiated
continuously
for
30
days
with
a
xenon
light
source
and
maintained
at
25
±
1
E
C
or
in
a
sterile
buffer
solution
used
as
dark
control.
[
14C]
ADBAC
accounted
for
>
99%
of
the
applied
radioactivity
at
30
days
post
treatment
in
the
sterile
buffer
solutions.
During
the
study,
the
material
balance
of
the
sterile
buffer
solutions
ranged
from
96.3
to
105%
of
the
applied
radioactivity.
In
contrast,
[
14C]
ADBAC
degraded
with
a
calculated
halflife
of
7.1
days
in
the
irradiated
solution
that
had
been
sensitized
with
1%
acetone.
The
parent
Page
7
of
14
compound
declined
from
76.9%
of
the
applied
radioactivity
at
3
days
post
treatment
to
approximately
37%
at
7
and
10
days,
and
16.3%
at
30
days
post
treatment.
An
unidentified
degradate
accounted
for
74.5%
of
the
applied
radioactivity.
[
14C]
ADBAC
did
not
degrade
in
the
sensitized
dark
control.
The
material
balance
of
the
sensitized
solutions
ranged
from
90.3
to
101%
of
the
applied
radioactivity
during
the
study.
Volatilization
of
[
14C]
residues
from
the
sensitized
and
nonsensitized
buffered
solutions
accounted
for
3.4­
5.4%
of
the
applied
radioactivity
during
30
days
of
incubation.

3.
Anaerobic
Aquatic
Metabolism
(
OPP
Guideline
No.
162­
3,
MRID
Nos.
411055­
01
&
424151­
01)

This
anaerobic
aquatic
metabolism
study
was
reviewed
by
the
Agency
and
found
to
be
acceptable
after
supplemental
information
was
submitted
by
the
Registrant
(
MRID
No.
424151­
02)
(
EFGB,
1993).
The
anaerobic
aquatic
metabolism
data
requirement
for
ADBAC
has
been
satisfied.
Information
was
extracted
directly
from
the
study
report
with
minor
editing
changes.

In
this
study,
samples
of
well
water
and
sandy
loam
soil,
preincubated
under
anaerobic
conditions
for
34
days,
were
fortified
with
[
14C]
ADBAC
at
a
nominal
test
concentration
of
10
µ
g/
g.
The
fortified
samples
were
placed
in
metabolism
vessels
in
an
environmental
chamber
maintained
at
an
average
temperature
of
25.2
±
0.5
E
C
under
dark
conditions.
The
treatment
samples
were
incubated
anaerobically
for
one
year
following
dosing.
In
addition
to
the
day
0
soil
and
water
analysis,
samples
of
soil,
water
and
trapping
solutions
were
collected
for
analysis
at
1,
3,
7,
14
days
post
treatment
and
1,
2,
3,
4,
6,
9
and
12
months
post
treatment.
Trapping
solutions
were
also
sampled
at
5,
7,
8,
10,
and
11
months.

On
each
sample
day,
sample
tubes
were
vortexed
and
centrifuged
to
separate
the
water
layer
from
the
soil.
The
aqueous
phase
was
pippetted
into
a
separate
silanized
tube
and
adjusted
to
volume
with
deionized
water.
The
remaining
soil
in
each
tube
was
extracted
three
times
with
dimehtylformamide:
acetic
acid.
Triplicate
aliquots
of
the
both
the
aqueous
phase
and
soil
extracts
were
analyzed
by
liquid
scintillation
counting
(
LSC)
to
determine
total
radioactivity.
Bound
residues
were
determined
by
combustion
of
triplicate
aliquots
of
the
post­
extracted
soil
followed
by
LSC
analysis.
The
trapping
solutions
were
also
analyzed
in
triplicate
by
LSC.
Thinlayer
chromatography
(
TLC)
was
used
to
characterize
[
14C]
residues
in
the
samples.

Throughout
the
year­
long
study,
[
14C]
residues
levels
in
the
water
remained
low
ranging
from
0.7
to
2.4%
of
the
total
residues
(
mean
value
of
1.2
±
0.4%).
The
non­
extractable
residues
of
[
14C]
ADBAC
accounted
for
10.9%
of
the
total
residues
at
the
end
of
the
study.
Volatilization
of
[
14C]
residues
was
minimal
with
only
0.3%
of
the
applied
dose
present
in
the
volatile
trap
samples
after
366
days
of
anaerobic
incubation.

The
parent
compound
was
the
only
compound
detected
in
the
TLC
analysis
of
the
soil
extracts.
The
recovery
of
[
14C]­
activity
from
the
thin­
layer
plates
ranged
from
89.1
to
106.1%
of
the
applied
radioactivity
(
mean
of
96.1
±
4.2%).
Most
of
the
radioactivity
recovered
was
in
the
zone
corresponding
to
the
co­
chromatographed
parent
compound.
The
mean
recovery
as
parent
compound
was
94.8
±
4.3%.
Based
on
the
levels
of
ADBAC
present
in
the
extractable
residues,
Page
8
of
14
the
half­
life
was
determined
to
be
1,815
days.
The
mass
balance
ranged
from
100
to
112
%
of
the
measured
day
0
levels
(
mean
of
106
±
4%).

4.
Aerobic
Aquatic
Metabolism
(
OPP
Guideline
No.
162­
4,
MRID
No.
408356­
04)

This
aerobic
aquatic
metabolism
study
was
reviewed
by
the
Agency
and
found
scientifically
valid.
In
its
original
review
the
Agency
noted
that
the
study
did
not
meet
guideline
requirements
since
several
[
14C]
residues
present
at
 
0.01
ppm
were
not
identified,
including
one
degradate
present
at
0.12
µ
g/
g
and
the
composite
of
all
the
scraped
TLC
material
known
as
"
remainder"
that
accounted
for
up
to
0.97
µ
g
/
g.
Supplemental
information
(
MRID
424149­
01)
submitted
by
the
Registrant
indicated
that
the
degradate
represents
only
a
minor
impurity,
not
a
metabolic
degradate,
and
was
not
detected
after
day
2.
In
addition,
the
"
remainder"
fraction
contained
only
nondistinct
components
that
were
less
than
1%
of
the
initial
dose.
After
review
of
the
supplemental
information,
the
Agency
concluded
that
the
study
is
acceptable
and
satisfies
the
aerobic
aquatic
metabolism
data
requirement
for
ADBAC
(
EFGB,
1993).

In
this
study,
samples
(
10
g)
of
sieved
(
2
mm)
sandy
loam
soil
(
64%
sand,
20%
silt,
16%
clay,
1.6%
organic
matter,
pH
6.2,
CEC
9.5
meq/
100
g)
were
weighed
into
silanized
culture
tubes
and
then
flooded
with
20
ml
of
well
water
that
had
been
treated
with
approximately
10
µ
g/
ml
of
ring­
labeled
[
14C]
ADBAC
(
alkyl
dimethyl
benzyl
ammonium
chloride;
radiochemical
purity
98%;
specific
activity
2.03
x
104
dpm/
µ
g).
The
treated
soil:
water
samples
were
homogenized
and
divided
between
two
3­
L
glass
metabolism
vessels.
Humidified
air
was
pumped
continuously
into
the
vessels
holding
the
tubes
of
soil;
effluent
air
was
then
passed
through
an
ethylene
glycol
trap,
a
1
N
sulfuric
acid
trap
and
two
1
N
potassium
hydroxide
traps.
The
test
tubes
were
maintained
at
24­
27
E
C
under
dark
conditions.
One
sample
was
collected
from
each
metabolism
vessel
at
0,
1,
2,
7,
14,
21,
and
30
days
post
treatment.
Volatile
traps
were
sampled
at
the
same
intervals.

At
each
sampling
interval,
soil:
water
samples
were
vortexed
and
centrifuged
and
the
aqueous
phase
decanted.
Aliquots
of
the
aqueous
phase
were
analyzed
for
total
radioactivity
by
liquid
scintillation
counting
(
LSC)
and
for
specific
compounds
using
normal­
phase
thin
layer
chromatography
(
TLC)
on
silica
gel
plates
developed
in
chloroform:
methanol:
formic
acid
(
60:
40:
20).
The
soil
fraction
was
extracted
three
times
with
dimethylformamide:
acetic
acid
(
80:
20);
the
extracts
were
separated
from
the
soil
by
centrifugation
and
combined.
Aliquots
of
the
extracts
were
analyzed
for
total
radioactivity
by
LSC
and
for
specific
compounds
using
normal­
phase
TLC
as
described
for
the
aqueous
phase
aliquots.
Unextractable
[
14C]
residues
in
the
soil
were
quantified
by
LSC
following
combustion.
Residues
were
corrected
for
combustion
recovery
efficiencies
in
controls.
Radioactivity
in
the
volatile
trapping
solutions
was
quantified
by
LSC.

Ring­
labeled
[
14C]
ADBAC,
at
approximately
10
µ
g/
g,
did
not
degrade
in
aerobic
flooded
sandy
loam
soil
that
was
incubated
in
the
dark
at
24­
27
E
C
for
30
days.
During
the
study,
the
soil
fraction
contained
9.19­
10.34
µ
g
of
radioactivity/
g
while
the
aqueous
fraction
contained
0.095­
0.204
µ
g
of
radioactivity/
g,
with
no
definitive
pattern.
More
than
90%
of
the
radioactivity
in
the
Page
9
of
14
soil
fraction
was
extractable.
In
the
soil
fraction,
there
was
a
steady
decrease
from
day
0
to
day
30
in
the
concentration
of
extractable
radioactivity
associated
with
the
origin
(
from
0.78
to
0.0%
of
the
recovered
radioactivity
from
the
TLC
plate),
with
an
unidentified
[
14C]
compound
at
Rf
0.15
(
from
0.92
to
0%),
and
with
the
remainder
radioactivity
(
from
11.3
to
1.63%).
The
remainder
radioactivity
was
defined
as
all
radioactivity
on
the
TLC
plate
that
was
not
associated
with
the
origin,
ADBAC,
or
the
unknown
at
Rf
0.15.
The
concentration
of
extractable
[
14C]
ADBAC
(
Rf
0.4)
increased
from
87.0%
at
day
0
to
98.4%
of
the
recovered
radioactivity
at
day
30.
Unextractable
[
14C]
residues
in
the
soil
fraction
increased
in
concentration
from
0.272
µ
g/
g
at
day
0
to
0.520
µ
g/
g
at
day
30.
In
the
water
fraction,
[
14C]
ADBAC
accounted
for
68.1­
86.3%
of
the
radioactivity
recovered
from
the
TLC
plate
while
the
origin
material
and
"
remainder"
comprised
0.92­
4.19%
and
10.9­
27.7%,
respectively.
Volatiles
accounted
for
a
small
fraction
of
the
radioactivity
(
1.36
µ
g)
at
day
30.
Recoveries
from
the
TLC
plates
ranged
from
86.4­
104%
of
the
applied
radioactivity
during
the
30
day
study.
The
material
balance
during
the
study
ranged
from
96.1
to
103.4%
of
the
nominal
application
rate.

5.
Adsorption/
Desorption
(
OPP
Guideline
No.
163­
1,
MRID
Nos.
408356­
05
&
424148­
01)

This
adsorption/
desorption
study
was
reviewed
by
the
Agency
and
found
scientifically
valid.
However,
the
study
only
provides
information
on
the
mobility
of
unaged
ADBAC.
The
adsorption/
desorption
data
requirements
for
ADBAC
has
been
partially
fulfilled.

Based
on
the
results
of
a
preliminary
study
of
the
adsorption
of
ring­
labeled
[
14C]
ADBAC
to
sand,
sandy
loam,
silt
loam,
and
clay
loam
soils,
a
soil:
solution
ratio
of
1:
200
and
an
equilibration
period
of
20
hours
were
chosen
for
the
definitive
adsorption
and
desorption
study.

In
the
definitive
study,
sand,
silt
loam,
sandy
loam,
and
clay
loam
soils
were
sieved
(
10
mesh
screen)
and
sterilized
by
autoclaving
at
250
°
F
(
121
°
C)
and
15
psi
for
1
hour.
Uniformly
ring­
labeled
[
14C]
ADBAC
was
purified
to
98.4%,
as
determined
by
TLC/
radiochemical
analysis,
and
mixed
with
non­
radiolabeled
ADBAC
(
specific
activity
2.03
x
104
dpm/
µ
g).

For
the
adsorption
phase
of
the
study,
subsamples
of
each
soil
were
weighed
into
nalgene
bottles
and
mixed
with
0.01
M
CaCl2
solution.
The
soil:
solution
slurries
(
1:
200)
were
individually
treated
at
nominal
concentrations
of
0.1,
0.5,
1.0,
and
2.0
µ
g/
ml
with
[
14C]
ADBAC.
After
shaking
the
bottles
for
20
hours
in
the
dark
at
25
±
1
E
C
(
adsorption
equilibration
period),
the
soil:
solution
slurries
were
centrifuged
and
aliquots
of
the
supernatant
were
analyzed
for
total
radioactivity
by
liquid
scintillation
counting
(
LSC).

For
the
desorption
phase
of
the
study,
196
ml
of
0.01M
CaCl2
were
added
to
each
sample.
The
soil:
solution
slurries
were
shaken
for
14
hours
and
45
minutes
and
centrifuged.
Aliquots
of
the
supernatant
were
analyzed
for
total
radioactivity
by
LSC.
The
soil
was
air
dried
and
analyzed
for
total
radioactivity
by
LSC
following
combustion.

Uniformly
phenyl
ring­
labeled
[
14C]
ADBAC,
at
approximately
0.1,
0.5,
1.0,
and
2.0
Page
10
of
14
µ
g/
ml,
was
determined
to
be
immobile
in
sterilized
sand,
silt
loam,
sandy
loam,
and
clay
loam
soil:
solution
slurries
(
1:
200)
that
were
equilibrated
in
the
dark
for
20
hours
at
25
±
1
E
C.
Freundlich
Kads
values
were
6,172
for
the
sand
soil,
10,797
for
the
silt
loam,
5,123
for
the
sandy
loam
soil,
and
32,429
for
the
clay
loam
and
the
corresponding
Koc
values
were
6,171,657
for
the
sand
soil,
2,159,346
for
the
silt
loam,
640,389
for
the
sandy
loam
soil,
and
1,663,039
for
the
clay
loam.
Following
the
first
desorption
step,
Freundlich
Kdes
values
were
7,137
for
the
sand
soil,
14,083
for
the
silt
loam
soil,
96,540
for
the
sandy
loam
soil,
and
165,556
for
the
clay
loam
soil;
corresponding
Koc
values
were
7,137,310
for
the
sand
soil,
2,816,590
for
the
silt
loam
soil,
12,067,457
for
the
sandy
loam
soil,
and
8,490,062
for
the
clay
loam
soil.
Material
balances
ranged
from
71.66
to
123.43%.

It
should
be
noted
that
the
soils
tested
in
this
study
were
sterilized
by
autoclaving
prior
to
the
experiment.
Autoclaving
affects
the
physical
and
chemical
properties
of
the
soils.
However,
the
Registrant
noted
that
at
the
time
the
protocol
was
developed,
the
use
of
autoclaved
soils
was
a
generally
accepted
practice.
It
was
also
noted
that
autoclaving
is
expected
to
enhance
the
apparent
mobility
of
the
chemical;
however,
the
results
of
the
study
showed
that
ADBAC
is
immobile.
The
Agency
concluded
that
the
results
are
acceptable
(
EFGB,
1993).

6.
Aquatic
Field
Dissipation
(
OPP
Guideline
No.
164­
2)

The
Agency
has
waived
data
requirements
for
an
aquatic
field
dissipation
study
for
ADBAC.

7.
Bioaccumulation
in
Fish
(
OPP
Guideline
No.
165­
4,
MRID
No.
410268­
01)

This
bioaccumulation
study
was
reviewed
by
the
Agency
and
found
scientifically
valid.
However,
the
study
does
not
meet
guidelines
for
the
fulfillment
of
data
requirements
for
ADBAC
on
the
bioaccumulation
in
fish
since
[
14C]
residues
present
at
0.05
ppm
or
greater
in
the
treated
water
and
fish
tissues
were
not
characterized.
This
study
was
classified
by
the
Agency
as
supplemental
(
EFGB,
1993).

Bluegill
sunfish
(
Lepomis
macrochirus;
average
length
65
mm,
average
weight
3.6
g)
were
maintained
in
a
cultured
tank
under
a
light/
dark
cycle
of
16
hours/
8
hours
for
at
least
14
days
prior
to
the
initiation
of
the
study.
Flow­
through
aquatic
exposure
systems
were
prepared
using
two
75­
L
aquaria
(
one
exposure
and
one
control).
Each
aquarium
was
continuously
supplied
with
well
water
(
pH
6.9­
7.1,
dissolved
oxygen
78­
88%
of
saturation,
hardness
24­
28
mg/
L
as
CaCO3,
alkalinity
19­
22
mg/
L
as
CaCO3,
temperature
18
°
C)
at
a
flow
rate
of
10
turnovers
per
day.
Bluegill
sunfish
(
190)
were
placed
in
each
aquarium.
The
exposure
aquarium
was
continuously
treated
with
ring­
labeled
[
14C]
ADBAC
(
alkyl
dimethyl
benzyl
ammonium
chloride;
radiochemical
purity
98.9%,
specific
activity
227013
dmp/
µ
g)
combined
with
unlabeled
ADBAC
(
30.64%
active),
at
a
concentration
of
0.05
ppm.

Water
samples
were
collected
from
the
exposure
and
control
aquaria
prior
to
introducing
the
fish
and
at
days
1,
3,
7,
8,
9,
10,
14,
21,
23,
28
and
35.
During
the
exposure
period,
five
fish
were
collected
from
the
exposure
aquarium
at
days
1,
3,
7,
10,
14,
21,
28
and
35.
Fish
were
Page
11
of
14
collected
from
the
control
aquarium
at
days
0,
9,
and
35.

Following
a
35­
day
exposure
period,
35
of
the
fish
remaining
in
the
exposure
aquarium
were
transferred
to
an
aquarium
containing
untreated
water
for
a
21­
day
depuration
period.
Water
samples
and
[
14C]
ADBAC­
treated
fish
(
5)
were
collected
during
the
depuration
period
on
days
1,
3,
7,
10,
14,
16
and
21.
Control
fish
were
collected
on
day
21.

At
each
sampling
interval,
water
samples
were
analyzed
for
total
radioactivity
by
liquid
scintillation
counting
(
LSC).
The
detection
limit
was
0.014
ppm.

Fish
from
the
exposure
and
depuration
periods
were
dissected
and
separated
into
edible
tissues
(
muscle
and
skin)
and
nonedible
tissues
(
viscera,
head
and
carcass).
The
edible
and
nonedible
fractions
were
analyzed
for
total
radioactivity
by
LSC
following
combustion;
the
limit
of
detection
was
0.1
ppm.
The
edible
tissue
fractions
from
additional
fish
(
three
sets
of
ten
fish)
collected
after
35
days
of
exposure
were
homogenized
with
dry
ice
and
extracted
with
hexane
followed
by
methanol.
The
extracts
were
analyzed
by
LSC
while
the
unextractable
radioactivity
remaining
in
the
tissues
were
quantified
by
LSC
following
combustion.
In
addition,
the
skins
from
ten
additional
fish
also
collected
after
35
days
of
exposure
were
analyzed
for
radioactivity
by
combustion
to
determine
if
external
surface
binding
of
the
test
substance
had
occurred.

Radiolabeled
residues
accumulated
in
bluegill
sunfish
that
were
exposed
for
35
days
to
uniformly
phenyl­
ring
labeled
[
14C]
ADBAC,
at
a
concentration
of
0.05
ppm,
under
flow­
through
aquarium
conditions.
Maximum
bioconcentration
factors
(
BCF)
were
33X
for
edible
tissues
(
muscle,
skin),
160X
for
nonedible
tissues
(
viscera,
head,
carcass),
and
79X
for
whole
fish
tissues.
The
maximum
concentrations
of
[
14C]
residues
(
day
35)
were
3.4,
13
and
6.6
ppm
in
edible
tissues,
nonedible
tissues
and
whole
fish,
respectively.

Of
the
total
radioactivity
found
in
the
edible
tissues,
1.2­
4.2%
was
extractable
into
hexane
and
6.7­
18.5%
was
extractable
into
methanol.
Unextractable
radioactivity
accounted
for
72­
89.3%
of
the
total
radioactivity
in
edible
tissues.
[
14C]
ADBAC
at
concentrations
of
2.7­
6.4
ppm
was
determined
in
the
skin
of
fish
after
35
days
of
exposure.

After
21
days
of
depuration,
14[
C]
residues
were
2.4
ppm
in
edible
tissues,
5.3
ppm
in
nonedible
tissues,
and
3.7
ppm
in
whole
fish
tissues.
14[
C]
residues
in
edible
tissues
did
not
decline
significantly
from
the
concentrations
detected
during
the
exposure
period.

8.
Aqueous
Availability
(
Leachability)
(
American
Wood­
Preservers'
Association
Standard
Method
E11­
97
"
Standard
Method
for
Determining
the
Leachability
of
Wood
Preservatives,
None)

Because
of
its
use
as
a
wood
preservative,
an
aqueous
availability
study
evaluating
the
leachability
of
ADBAC
from
treated
wood
is
required.
However,
no
data
have
been
submitted
to
the
Agency.
Page
12
of
14
9.
Assessment
of
the
Biodegradability
of
ADBAC
and
DDAC
(
No
MRID
Number)

This
report
is
an
assessment
of
the
biodegradability
of
ADBAC
and
DDAC
based
on
the
review
of
information
from
the
open
literature,
unpublished
sources
and
meeting
proceedings.
It
also
provides
a
summary
of
the
current
information
available
on
the
environmental
fate
of
ADBAC
and
DDAC.
The
report
was
submitted
by
the
registrant
to
EPA,
but
has
not
been
reviewed
by
the
Agency.

Based
on
the
review
of
the
studies
in
the
report,
Lee
(
1992)
concluded
that:

"
Results
of
studies
published
in
the
open
literature,
literature
reviews,
conference
proceedings
and
information
obtained
from
unpublished
sources
indicate
that
ADBAC
and
DDAC
are
biodegradable
with
the
rate
and
extent
of
degradation
influenced
by
quat
concentration,
alkyl
chain
length,
the
presence
of
anionic
moieties,
and
the
type
of
microbes.
These
factors
and
the
design
of
the
test
system
are
important
in
interpreting
the
reliability
of
biodegradability
test
results.

After
release
of
ADBAC
and
DDAC
to
domestic
waste
streams
or
in
the
open
environment,
a
combination
of
physical
and
chemical
properties,
in
addition
to
biodegradability,
influence
their
fate
through
the
environmental
compartments
of
air,
water,
soil/
sediment
and
biota.
Important
properties
for
evaluating
the
environmental
fate
of
these
materials
include
solubility,
vapor
pressure,
surface
activity
and
adsorptive
properties."

In
a
study
by
Dobbs
et
al.,
1995,
biodegradation
was
studied
under
aerobic
conditions
using
the
CO2
production
test.
The
OECD
guideline
used
states
that
if
>
60%
of
the
theoretical
CO2
is
produced
in
28
days,
then
the
chemical
is
considered
readily
biodegradable.
The
results
show
that
65.9%
of
the
possible
theoretical
CO2
was
released
in
29
days
in
the
10
mg/
L
ADBAC
treatment,
but
only
6.8%
was
released
in
the
20
mg/
L
ADBAC
treatment.
The
authors
suggest
that
the
treatment
at
the
lower
concentration
indicates
that
ADBAC
is
readily
biodegradable,
but
that
at
the
higher
concentration
is
bactericidal.
Use
of
ADBAC
as
a
molluscicide
is
suggested
at
concentrations
of
2.5
mg/
L.
Therefore,
the
authors
concluded
that
results
of
this
test
suggest
that
ADBAC
would
be
biodegradable
under
the
conditions
specified
for
its
use.
Page
13
of
14
BIBLIOGRAPHY
MRID
Citation
408356­
02
Carpenter,
M.
and
M.
Fennessey.
1988.
Hydrolysis
of
ADBAC
as
a
function
of
pH
at
25
°
.
ABC
Amended
Final
Report
#
35712.
Unpublished
study
performed
by
Analytical
Bio­
Chemistry
Laboratories,
Inc.,
Columbia,
MO,
and
submitted
by
Chemical
Specialties
Manufacturers
Association,
Washington,
DC.

408356­
03
Carpenter,
M.
and
M.
Fennessey.
1988.
Determination
of
the
photolysis
rate
of
ADBAC
in
pH
7
buffered
solution
at
25
°
C.
ABC
Final
Report
#
35713.
Unpublished
study
performed
by
Analytical
Bio­
Chemistry
Laboratories,
Inc.,
Columbia,
MO,
and
submitted
by
Chemical
Specialties
Manufacturers
Association,
Washington,
DC.

408356­
04
Daly,
D.
and
W.
Cranor.
1988.
Aerobic
aquatic
metabolism
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alkyl
dimethyl
benzyl
ammonium
chloride.
ABC
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35715.
Unpublished
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performed
by
Analytical
Bio­
Chemistry
Laboratories,
Inc.,
Columbia,
MO,
and
submitted
by
Chemical
Specialties
Manufacturers
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Washington,
DC.

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05
Daly,
D.
and
W.
Cranor.
1992.
Soil/
Sediment
Adsorption­
Desorption
of
Alkyl
Dimethyl
Ammonium
Chloride.
Performed
by
ABC
Laboratories,
Inc.,
Columbia,
Missouri.
Submitted
by
ADBAC
Joint
Venture/
Chemical
Specialties
Manufacturers
Association,
Washington,
DC.

410268­
01
Flacker,
P.
1989.
Bioconcentration
and
elimination
of
14C­
residues
by
bluegill
(
Lepomis
macrochirus)
exposed
to
alkyl
dimethyl
benzyl
ammonium
chloride
(
ADBAC).
Study
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11572­
0287­
6103­
140B,
Report
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89­
1­
2921.
Unpublished
study
performed
by
Springborn
Life
Sciences,
Inc.,
Wareham,
MA,
and
submitted
by
ADBAC
Quat
Joint
Venture/
Chemical
Specialties
Manufacturers
Assoc.,
Washington,
DC.

411055­
01
Daly,
D.
and
W.
Cranor.
1989.
Anaerobic
aquatic
metabolism
of
alkyl
dimethyl
benzyl
ammonium
chloride.
ABC
Amended
Final
Report
#
35714.
Unpublished
study
performed
by
Analytical
Bio­
Chemistry
Laboratories,
Inc.,
Columbia,
MO,
and
submitted
by
ADBAC
Joint
Venture/
Chemical
Specialties
Manufacturers
Association,
Washington,
DC.

424148­
01
Daly,
D.
and
W.
Cranor.
1992.
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Chloride.
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408356­
05.
Performed
by
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Columbia,
Missouri.
Submitted
by
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Joint
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Chemical
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Manufacturers
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Washington,
DC.
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01
Daly,
D.
and
W.
Cranor.
1992.
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alkyl
dimethyl
benzyl
ammonium
chloride.
Supplement
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408356­
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Performed
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ABC
Laboratories,
Inc.,
Columbia,
Missouri.
Submitted
by
ADBAC
Joint
Venture/
Chemical
Specialties
Manufacturers
Association,
Washington,
DC.

424151­
01
Daly,
D.
and
W.
Cranor.
1989.
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metabolism
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alkyl
dimethyl
benzyl
ammonium
chloride.
ABC
Amended
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#
35714.
Supplement
in
support
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MRID#
411055­
01.
Unpublished
study
performed
by
Analytical
Bio­
Chemistry
Laboratories,
Inc.,
Columbia,
MO,
and
submitted
by
ADBAC
Joint
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Chemical
Specialties
Manufacturers
Association,
Washington,
DC.

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02
Daly,
D.
and
W.
Cranor.
1992.
Anaerobic
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alkyl
dimethyl
benzyl
ammonium
chloride.
Supplement
in
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411055­
01.
Performed
by
ABC
Laboratories,
Inc.,
Columbia,
Missouri.
Submitted
by
ADBAC
Joint
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Chemical
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Manufacturers
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Washington,
DC.

424152­
01
Carpenter,
M.
and
M.
Fennessey.
1992.
Determination
of
the
photolysis
rate
of
ADBAC
in
pH
7
buffered
solution
at
25
°
C.
Supplement
in
support
of
MRID#
408356­
03.
Performed
by
ABC
Laboratories,
Inc.,
Columbia,
Missouri.
Submitted
by
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Joint
Venture/
Chemical
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Manufacturers
Association,
Washington,
DC.

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M.
G.,
Cherry,
D.
S.,
Scott,
J.
C.,
Petrille,
J.
C.
1995.
Environmental
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an
Alkyl
Dimethyl
Benzyl
Ammonium
Chloride
(
ADBAC)
Based
Molluscicide
Using
Laboratory
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Virginia
Tech
University
Center
for
Environmental
and
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Materials
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VA
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and
Groundwater
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(
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1993.
EFGB
review
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benzyl
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J.
Lee,
Antimicrobial
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Lee,
C.
1992.
Assessment
of
the
Biodegradability
of
ADBAC
and
DDAC.
Unpublished
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prepared
by
Roy
F.
Weston,
Inc.
Contractor's
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