1
UNITED
STATES
ENVIRONMENTAL
PROTECTION
AGENCY
WASHINGTON,
D.
C.
20460
OFFICE
OF
PREVENTION,
PESTICIDES
AND
TOXIC
SUBSTANCES
September
29,
2005
MEMORANDUM
SUBJECT:
Revised
Environmental
Fate
Assessment
of
4­
tert­
Amylphenol
and
its
Potassium
and
Sodium
salts
for
the
Reregistration
Eligibility
Decision
(
RED)
Document
Case
No.:
3016
DP
Barcode:
322006
FROM:
Srinivas
Gowda,
Microbiologist/
Chemist
Risk
Assessment
and
Science
Support
Branch
(
RASSB)
Antimicrobials
Division
(
7510C)

TO:
Mark
Hartman,
Branch
Chief
Benjamin
Chambliss,
Team
Leader
Killian
Swift,
Chemical
Review
Manager
Regulatory
Management
Branch
II
Antimicrobials
Division
(
7510C)

Deborah
Smegal,
Risk
Assessor
Risk
Assessment
and
Science
Support
Branch
(
RASSB)
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
4­
tert­
Amylphenol
064101
80­
46­
6
p­
tert­
amylphenol
Potassium
4­
tert­
amylphenate
064111
53404­
18­
5
Potassium
p­
tert­
amylphenate
Sodium
4­
tert­
amylphenate
064112
31366­
95­
7
Sodium
p­
tert­
amylphenate
Environmental
Fate
Science
Chapter
and
Fate
Assessment
on
4­
tert­
Amylphenol
and
its
2
potassium
and
sodium
salts
is
submitted
for
Reregistration
Eligibility
Decision
(
RED).

EXECUTIVE
SUMMARY
Environmental
Fate
Assessment:

The
environmental
fate
assessment
for
4­
tert­
Amylphenol
and
its
potassium
and
sodium
salts
is
based
on
US
EPA
=

s
Estimation
Programs
Interface
(
EPI)
Suite.
EPI
Suite
provides
estimations
of
physical/
chemical
properties
and
environmental
fate
properties.

4­
tert­
Amylphenol
may
be
bioaccumlative
(
log
KOW
3.91)
and
is
likely
to
pose
a
concern
for
aquatic
organisms.
It
is
expected
to
have
moderate
to
slight
mobility
in
soils
based
upon
the
estimated
Koc
value
of
3799.
Estimated
value
for
biodegradation
probability
indicates
that
it
may
biodegrade
linearly
within
days
in
aquatic
medium.
However,
ultimate
biodegradation
(
mineralization)
may
take
months.
Ready
Biodegradability
study
results
also
indicate
that
the
relationship
between
biodegradation
of
4­
tert­
Amylphenol
and
time
appears
to
be
linier
in
an
aqueous
medium
and
ultimate
biodegradation
would
occur
over
a
period
longer
than
a
month.
It
is
volatile
and
may
vaporize
into
atmosphere.
The
estimated
half
life
in
the
air
for
4­
tert­
Amylphenol
is
about
three
hours
which
indicates
that
it
is
not
persistent
in
air.
Because
of
the
possibility
of
biodegradation
in
water
and
soils,
it
is
not
likely
to
contaminate
surface
and
ground
waters.

p­
tert­
Amylphenol,
potassium
salt,
is
not
likely
to
be
bioaccumlative
(
log
KOW
1.23)
and
may
not
pose
a
concern
for
bioconcentration
in
aquatic
organisms.
It
may
be
expected
to
have
moderate
to
slight
mobility
in
soils
as
its
estimated
Koc
value
is
3799.
Estimated
probability
of
biodegradation
of
p­
tert­
Amylphenol,
potassium
salt,
in
soils
and
water
indicates
that
it
is
likely
to
biodegrade
within
days
to
weeks.
Therefore,
it
may
be
unlikely
that
soil
and
water
contamination
would
take
place.
It
has
low
volatility
and
its
estimated
half
life
in
air
is
about
4.68
hours
and
is
not
likely
to
be
persistent
in
air.

p­
tert­
Amylphenol,
sodium
salt,
is
not
likely
to
be
bioaccumlative
(
log
KOW
is
1.23)
and
may
not
pose
a
concern
for
bioconcentration
in
aquatic
organisms.
It
may
be
expected
to
have
moderate
to
slight
mobility
in
soils
as
its
estimated
Koc
value
is
the
same
as
the
parent
molecule,
4­
tert­
Amylphenol.
Probability
for
Sodium
4­
tert­
amylphenate
biodegradation
is
the
same
as
the
parent
molecule,
4­
tert­
Amylphenol.
Hence
it
is
not
likely
to
persist
in
soils
and
water,
and
surface
and
ground
water
contamination
is
not
likely
to
occur.
It
has
low
volatility
and
its
estimated
half
life
in
air
is
about
4.68
hours
and
is
not
likely
to
be
persistent
in
air.
3
4
APPENDIX
Environmental
Fate
Science
Chapter
for
para­
tert­
amylphenol:

4­
tert­
Amylphenol
is
registered
as
an
active
product
and
is
used
as
bactericide/
fungicide/
fungistat.
For
the
Reregistration
Eligibility
Decision
(
RED)
process
the
Agency
used
an
in­
house
database
program,
Estimation
Programs
Interface
(
EPI)
Suite,
and
open
literature
(
Toxnet)
to
obtain
fate
properties
of
para­
tert­
Amylphenol.
The
Agency
lacks
database
on
environmental
fate/
transport
properties
of
p­
tert­
Amylphenol.
Hence
Agency
made
use
of
the
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).
The
following
fate
properties
were
obtained
from
EPI
Suite
and
TOXNET.

1.
Vapor
Pressure:
0.00116
mm
Hg
at
25oC
(
1)

2.
Henry
=

s
law
Constant
(
air/
water
partition
coefficient):
2.03
x
10­
6
atm­
m3/
mole
at
25oC
(
1)

3.
Log
KOC
(
organic
carbon
ratio
in
soil):
3.57
(
Koc:
3799
)
(
1)

4.
Log
KOW
(
octanol/
water
partition
coefficient):
3.91
(
1)

5.
Water
solubility:
113
mg/
L
(
1)

6.
Log
bioconcentration
factor
(
BCF)
is
2.313
(
BCF
=
205.7)
(
1)

7.
Medium
to
slight
soil
mobility.
(
1)

8.
May
undergo
direct
air
photolysis,
half
life
in
air
(
estimated)
is
3.07
hours
due
to
induced
photochemical
reaction
of
atmospheric
hydroxyl
radical
(
2)

9.
Abiotic
Degradation:
Phenols
are
generally
resistant
to
aqueous
environmental
hydrolysis.
Therefore,
4­
tert­
Amylphenol
is
not
expected
to
hydrolyze
in
environmental
media
(
SRC)
(
2)

The
estimated
value
for
biodegradation
probability
indicates
that
4­
t­
amylphenol
may
biodegrade
linearly
within
days
in
aquatic
medium.
However,
ultimate
biodegradation
(
mineralization)
may
take
months.
Aquatic
hydrolysis,
oxidation,
volatilization,
bioconcentration,
and
adsorption
to
sediment
are
not
expected
to
be
significant
fate
processes
for
para­
tert­
Amylphenol
because
of
its
lack
of
hydrolyzable
hydrogen.
Because
of
a
low
Henry
=

s
Law
Constant,
volatilization
of
para­
tert­
Amylphenol
to
partition
from
surface
water
to
air
is
likely
to
be
minimum.
Based
upon
Koc
value
of
3799,
para­
tert­
Amylphenol
has
a
moderate
to
slight
soil
mobility.
Adsorption
to
sediment
is
not
expected
to
be
important
fate
process.
The
KOW
indicates
that
bioaccumulation
in
aquatic
organisms
like
fish
is
not
likely.
With
a
vapor
pressure
of
0.00116
mm
Hg
at
25oC
para­
tert­
Amylphenol
likely
to
vaporize
easily
from
soils
and
degrades
rapidly
by
reaction
with
photochemically
produced
hydroxyl
radicals
(
half­
life
of
~
3.07
hours)
in
air.

Ready
Biodegradability
(
OPPTS
Guideline
No.
835.3110,
MRID
No.
466247­
01)
(
3)

This
study
was
reviewed
by
the
Agency,
and
satisfies
the
OPPTS
835.3110
guideline
requirements
for
a
biodegradation
study.
Biodegradability
was
investigated
under
aerobic
static
exposure
conditions
using
the
CO2
Evolution
Test.
5
Based
on
the
data
of
the
individual
inorganic
carbon
determinations,
the
mean
biodegradability
in
the
CO2
Evolution
Test
of
p­
tert­
Amylphenol
was
calculated
to
be
73%
after
28
days.
The
biodegradation
of
p­
tert­
Amylphenol
reached
52%
at
the
end
of
the
10­
day
window.
Significant
biodegradation
of
the
test
substance
was
observed
after
a
lag
phase
of
about
7
days.
The
procedural
control,
sodium
benzoate,
reached
86%
biodegradation
after
14
days.
This
confirms
the
validity
of
the
test,
as
the
OPPTS
guidelines
require
that
the
procedural
control
reach
at
least
60%
degradation
by
day
14.
p­
tert­
Amylphenol
did
not
reach
the
pass
level
of
60%
for
ready
biodegradability
in
the
CO2
Evolution
Test
within
the
10­
day
window.

The
results
from
the
ready
biodegradability
study
are
consistent
with
the
above
stated
biodegradation
statements
based
on
the
estimated
value.
The
relationship
between
biodegradation
of
the
test
chemical
and
time
appears
to
be
linear
based
on
inspection
of
the
graph
presented
in
the
ready
biodegradation
study
report.
The
p­
tert­
Amylphenol
was
found
not
to
be
readily
biodegradable.
Over
the
28­
day
test
period,
73%
degradation
had
occurred,
suggesting
that
ultimate
biodegradation
would
occur
over
a
period
longer
than
a
month.

Surface
water
and
Ground
Water
Contamination:

4­
tert­
Amylphenol
has
been
found
in
an
effluent
sample
from
a
municipal
waste
water
treatment
plant.
However,
the
estimated
value
for
biodegradation
indicates
it
may
biodegrade
linearly
within
days
in
the
aquatic
environment.
Ultimate
biodegradation
(
mineralization)
may
take
months.
It
is
also
volatile
based
on
its
vapor
pressure
of
0.00116
mmHg,
and
has
a
moderate
to
slight
mobility
in
soils
based
on
its
estimated
Koc
value
of
3799.
Thus,
it
is
not
likely
to
contaminate
surface
and
ground
waters.
6
Environmental
Fate
Science
Chapter
For
para­
tert­
Amylphenol,
potassium
salt:

p­
tert­
Amylphenol,
potassium
salt,
is
registered
as
an
active
product.
For
the
Reregistration
Eligibility
Decision
(
RED)
process
the
Agency
used
an
in­
house
database
program,
Estimation
Programs
Interface
(
EPI)
Suite,
and
open
literature
(
Toxnet)
to
obtain
fate
properties
of
p­
tert­
Amylphenol,
potassium
salt.
The
Agency
lacks
database
on
environmental
fate/
transport
properties
of
p­
tert­
Amylphenol.
Hence
Agency
made
use
of
the
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).
The
following
fate
properties
were
obtained
from
EPI
Suite.

1.
Vapor
Pressure:
7.7
x
10­
10
mm
Hg
at
25oC
(
1)

2.
Henry
law
Constant
(
air/
water
partition
coefficient):
5.379
x
10­
14
atm­
m3/
mole
at
25oC
(
1)

3.
Log
KOC
(
organic
carbon
ratio
in
soil):
3.57
(
KOC:
3799)
(
1)

4.
Log
KOW
(
octanol/
water
partition
coefficient):
1.23
(
1)

5.
Water
solubility:
3811
mg/
L
(
1)

6.
Log
bioconcentration
factor
(
BCF)
is
2.313
(
BCF
=
205.7)
(
1)

7.
Medium
to
slight
mobility
in
soil.
(
1)

8.
May
undergo
direct
air
photolysis,
half
life
in
air
(
estimated)
is
4.68
hours
due
to
induced
photochemical
reaction
of
atmospheric
hydroxyl
radical.(
1)

Estimated
probability
of
biodegradation
of
p­
tert­
Amylphenol,
potassium
salt,
in
soils
and
water
indicates
that
it
is
likely
to
biodegrade
within
days
to
weeks.
Aquatic
hydrolysis,
oxidation,
volatilization,
bioconcentration,
and
adsorption
to
sediment
are
not
expected
to
be
significant
fate
processes
for
p­
tert­
Amylphenol,
potassium
salt,
because
of
its
lack
of
hydrolyzable
hydrogen.
Because
of
a
low
Henry
=

s
Law
Constant,
volatilization
of
p­
tert­
Amylphenol,
potassium
salt,
to
partition
from
surface
water
to
air
is
likely
to
be
minimum.
Koc
value
of
3799
indicates
that
paratert
Amylphenol,
potassium
salt,
has
a
moderate
to
slight
soil
mobility.
The
KOW
indicates
that
bioaccumulation
in
aquatic
organisms
like
fish
is
not
likely.
The
estimated
BCF
(
205.7)
value
indicates
that
bioaccumulation
is
likely
be
low.
p­
tert­
Amylphenol,
potassium
salt
degrades
rapidly
by
reaction
with
photochemically
produced
hydroxyl
radicals
(
half­
life
of
~
4.68
hours)
in
air.

Surface
Water
and
Ground
Water
Contamination:

Due
to
a
Koc
value
of
3799,
p­
tert­
Amylphenol,
potassium
salt,
has
a
moderate
to
slight
mobility
in
soil.
Biodegradation
of
p­
tert­
Amylphenol,
potassium
salt,
is
likely,
based
on
estimated
high
probability
of
linear
biodegradation.
Estimated
probability
of
biodegradation
of
ptert
Amylphenol,
potassium
salt,
in
soils
and
water
indicates
that
it
is
likely
to
biodegrade
within
days
to
weeks.
Thus,
it
is
unlikely
that
there
will
be
soil
and
water
contamination.
7
Environmental
Fate
Science
Chapter
For
para­
tert­
Amylphenol,
sodium
salt:

p­
tert­
Amylphenol,
sodium
salt,
is
registered
as
an
active
product.
For
the
Reregistration
Eligibility
Decision
(
RED)
process
the
Agency
used
an
in­
house
database
program,
Estimation
Programs
Interface
(
EPI)
Suite,
and
open
literature
(
Toxnet)
to
obtain
fate
properties
of
p­
tert­
Amylphenol,
sodium
salt.
The
Agency
lacks
database
on
environmental
fate/
transport
properties
of
p­
tert­
Amylphenol.
Hence
Agency
made
use
of
the
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).
The
following
fate
properties
were
obtained
from
EPI
Suite.

1.
Vapor
Pressure:
7.7
x
10­
10
mm
Hg
at
25oC
(
1)

2.
Henry
law
Constant
(
air/
water
partition
coefficient):
4.10
x
10­
14
atm­
m3/
mole
at
25oC
(
1)

3.
Log
KOC
(
organic
carbon
ratio
in
soil):
3.57
(
KOC:
3799)
(
1)

4.
Log
KOW
(
octanol/
water
partition
coefficient):
1.23
(
1)

5.
Water
solubility:
4595
mg/
L
(
1)

6.
Log
bioconcentration
factor
(
BCF)
is
2.313
(
BCF
=
205.7)
(
1)

7.
Medium
to
slight
mobility
in
soil.
(
1)

8.
May
undergo
direct
air
photolysis,
half
life
in
air
(
estimated)
is
4.68
hours
due
to
induced
photochemical
reaction
of
atmospheric
hydroxyl
radical.(
1)

Estimated
probability
of
biodegradation
of
p­
tert­
Amylphenol,
sodium
salt,
in
soils
and
water
indicates
that
it
is
likely
to
biodegrade
within
days
to
weeks.
Aquatic
hydrolysis,
oxidation,
volatilization,
bioconcentration,
and
adsorption
to
sediment
are
not
expected
to
be
significant
fate
processes
for
p­
tert­
Amylphenol,
sodium
salt,
because
of
its
lack
of
hydrolyzable
hydrogen.
Because
of
a
low
Henry
=

s
Law
Constant,
volatilization
of
p­
tert­
Amylphenol,
sodium
salt,
to
partition
from
surface
water
to
air
is
likely
to
be
minimum.
Koc
value
of
3799
indicates
that
paratert
Amylphenol,
sodium
salt,
has
a
medium
to
slight
soil
mobility.
The
KOW
indicates
that
bioaccumulation
in
aquatic
organisms
like
fish
is
not
likely.
The
estimated
BCF
(
205.7)
value
indicates
that
bioaccumulation
is
likely
be
low.
p­
tert­
Amylphenol,
sodium
salt,
degrades
rapidly
by
reaction
with
photochemically
produced
hydroxyl
radicals
(
half­
life
of
~
4.68
hours)
in
air.

Surface
Water
and
Ground
Water
Contamination:

Due
to
a
Koc
value
of
3799,
p­
tert­
Amylphenol,
sodium
salt,
has
a
moderate
to
slight
mobility
in
soil.
Biodegradation
of
p­
tert­
Amylphenol,
sodium
salt,
in
soil
is
likely,
based
on
the
estimated
high
probability
of
linear
biodegradation.
Estimated
probability
of
biodegradation
of
ptert
Amylphenol,
sodium,
in
soils
and
water
indicates
that
it
is
likely
to
biodegrade
within
days
to
8
weeks.
Thus,
it
is
unlikely
that
there
will
be
soil
and
water
contamination.

Data
Gap:

Para­
tert­
amylphenol
and
its
potassium
and
sodium
salts
are
registered
as
indoor
use
products
and
minimum
environmental
fate
data
required
by
EPA
for
an
indoor
use
product
is
hydrolysis
(
161­
1).
However,
no
hydrolysis
data
as
indicated
in
the
U.
S.
Environmental
Protection
Agency's
Environmental
Fate
Data
Requirements
published
in
Pesticide
Assessment
Guidelines,
Subdivision
N,
§
161­
1
have
been
submitted
to
the
Agency
for
these
chemicals.
9
BIBLIOGRAPHY
MRID
Citation
­­­­­­­­­­­­­­
(
1)
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
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SRC).
http://
www.
epa.
gov/
opptintr/
exposure/
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EPISuitedl.
htm
­­­­­­­­­­­­­
(
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Hazard
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Library
of
Medicine
=

s
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46624701
(
3)
Haner,
A.
1999.
p­
tert.­
Amylphenol:
Ready
Biodegradability
 
Evaluation
of
the
Aerobic
Biodegradability
in
an
Aqueous
Medium:
OECD
301
B:
CO2
Evolution
Test.
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