Document ID: EPA-HQ-OPP-2006-0366-0011
Agency: epa
Document Type: Supporting & Related Material
Title: 
Posted Date: 2006-08-11T04:00Z

Bifenthrin/
128825/
IR­
4
DACO
7.4.1/
7.4.2/
OPPTS
860.1500/
OECD
IIA
6.3.1,
6.3.2,
6.3.3
and
IIIA
8.3.1,
8.3.2,
8.3.3
Crop
Field
Trial
 
Mustard
Greens
DP#:
310089/
MRID#:
45660301
Page
1
of
8
Primary
Evaluator:
Sarah
J.
Levy,
Chemist
Registration
Action
Branch
1
(
RAB1)
Health
Effects
Division
(
HED;
7509C)
Date:
06­
APR­
2006
Approved
by:
George
Kramer,
Ph.
D.,
Chemist
RAB1/
HED
(
7509C)
Date:
06­
APR­
2006
This
DER
was
originally
prepared
under
contract
by
Dynamac
Corporation
(
1910
Sedwick
Road,
Building
100,
Suite
B,
Durham,
NC
27713;
submitted
10/
17/
2005).
The
DER
has
been
reviewed
by
HED
and
revised
to
reflect
current
Office
of
Pesticide
Programs
(
OPP)
policies.

STUDY
REPORT:

45660301.
Samoil,
K.
(
2002)
Bifenthrin:
Magnitude
of
the
Residue
on
Greens
(
Mustard).
Lab
Project
Number:
06970.99­
MIR03.
Study
No
06970.
Unpublished
study
prepared
by
IR­
4
Project,
Center
for
Minor
Crop
Pest
Management.
136
pages.

EXECUTIVE
SUMMARY:

Field
trials
on
mustard
greens
were
conducted
at
eight
trial
sites
in
FL
(
1),
GA
(
2),
TN
(
1),
TX
(
1),
WI
(
1),
and
CA
(
2)
during
the
1999
growing
season.
Bifenthrin
(
2
lb/
gal
emulsifiable
concentrate
(
EC))
was
applied
as
four
broadcast
foliar
applications
to
mustard
greens
at
0.097­
0.110
lb
ai/
A/
application,
for
a
total
of
0.397­
0.427
lb
ai/
A/
season.
Applications
were
made
during
vegetative
growth,
at
retreatment
intervals
(
RTI)
of
6­
8
days.
Duplicate
control
and
treated
samples
of
fresh
mustard
greens
were
harvested
at
commercial
maturity
from
each
trial
site
at
6­
7
day
pre­
harvest
intervals
(
PHIs).
Samples
were
stored
frozen
for
up
to
2
months
prior
to
analysis,
an
interval
supported
by
the
available
storage
stability
data.

The
gas
chromatography
(
GC)/
electron­
capture
detector
(
ECD)
method
(
FMC
Corporation
Report
No.
P­
2132M,
modified)
used
to
determine
bifenthrin
residues
in/
on
mustard
greens
was
adequately
validated
in
conjunction
with
the
field
trial
analyses.
Briefly,
bifenthrin
residues
are
extracted
with
hexane
under
high
pressure
and
temperature
using
an
automated
solvent
extraction
system
(
Dionex
ASE­
200).
The
residues
were
then
analyzed
by
GC/
ECD
using
a
capillary
DB­
1
column.
The
validated
limit
of
quantitation
(
LOQ)
was
0.05
ppm.
The
limit
of
detection
(
LOD)
was
not
calculated
or
estimated.

Bifenthrin
residues
were
0.05­
2.05
ppm
in/
on
16
samples
of
mustard
greens
harvested
at
6­
7
day
PHIs.
The
average
and
highest­
average
field
trial
(
HAFT)
residues
in/
on
mustard
greens
were
1.04
and
2.01
ppm,
respectively.
Residue
decline
data
were
not
provided.

STUDY/
WAIVER
ACCEPTABILITY/
DEFICIENCIES/
CLARIFICATIONS:

Under
the
conditions
and
parameters
used
in
the
study,
the
mustard
green
field
trial
residue
data
are
classified
as
scientifically
acceptable.
The
acceptability
of
this
study
for
regulatory
purposes
is
addressed
in
the
forthcoming
U.
S.
EPA
Residue
Chemistry
Summary
Document
[
DP#:
310089].
Bifenthrin/
128825/
IR­
4
DACO
7.4.1/
7.4.2/
OPPTS
860.1500/
OECD
IIA
6.3.1,
6.3.2,
6.3.3
and
IIIA
8.3.1,
8.3.2,
8.3.3
Crop
Field
Trial
 
Mustard
Greens
DP#:
310089/
MRID#:
45660301
Page
2
of
8
COMPLIANCE:

Signed
and
dated
Good
Laboratory
Practice
(
GLP),
Quality
Assurance
and
Data
Confidentiality
statements
were
provided.
The
study
author
noted
numerous
minor
deviations
from
GLP
compliance
at
several
trial
sites
pertaining
to
collection
of
data
on
weather,
agricultural
practices,
maintenance
fertilizers
and
pesticides,
raw
data
collection,
and
one
trial,
CA15,
where
temperature
data
for
the
untreated
sample
freezer
was
not
collected
for
the
first
three
days.
However,
none
of
these
deviations
substantially
impacts
the
validity
of
the
study.

A.
BACKGROUND
INFORMATION
Bifenthrin
is
a
non­
systemic
insecticide/
miticide
in
the
class
of
synthetic
pyrethroids.
Bifenthrin
is
formulated
as
a
2.0
lb/
gal
EC
and
is
marketed
by
FMC
Corporation
under
the
trade
name
Capture
®
2
EC
(
EPA
Reg.
No.
279­
3069).

TABLE
A.
1.
Nomenclature
of
Bifenthrin.

Compound
O
O
Cl
F
3
C
CH
3
CH
3
C
H
3
Common
name
Bifenthrin
Company
experimental
names
Capture
®
2
EC
IUPAC
name
2­
methylbiphenyl­
3­
ylmethyl(
Z)­(
1RS,
3RS)­
3­(
2­
chloro­
3,3,3­
trifluoroprop­
1­
enyl)­
2,2dimethylcyclopropanecarboxylate
or
2­
methylbiphenyl­
3­
ylmethyl(
Z)­(
1RS)­
cis­
3­(
2­
chloro­
3,3,3­
trifluoroprop­
1­
enyl)­
2,2dimethylcyclopropanecarboxylate
CAS
name
rel­
2­
methyl(
1,1'­
biphenyl)­
3­
yl)
methyl(
1R,
3R)­
3­((
1Z)­
2­
chloro­
3,3,3­
trifluoro­
1­
propenyl)­
2,2­
dimethylcyclopropanecarboxylate
CAS
#
82657­
04­
03
End­
use
products/
EP
2.0
lb/
gal
EC
(
EPA
Reg.
No.
279­
3069)
Bifenthrin/
128825/
IR­
4
DACO
7.4.1/
7.4.2/
OPPTS
860.1500/
OECD
IIA
6.3.1,
6.3.2,
6.3.3
and
IIIA
8.3.1,
8.3.2,
8.3.3
Crop
Field
Trial
 
Mustard
Greens
DP#:
310089/
MRID#:
45660301
Page
3
of
8
TABLE
A.
2.
Physicochemical
Properties
of
the
Technical
Grade
Bifenthrin.

Parameter
Value
Reference
Melting
point/
range
68­
70.6
°
C
pH
NA
Density
at
24
°
C
1.26
g/
mL
Water
solubility
<
0.1
Fg/
L
Solvent
solubility
(
g/
100
mL)
8.9
in
heptane
and
methanol
125
in
acetone,
chloroform,
ether,
methylene
chloride,
and
toluene
Vapor
pressure
(
Pa)
at
25
°
C
2.41
x
10­
5
Dissociation
constant
(
pKa)
NA
Octanol/
water
partition
coefficient)
Kow
>
1
x
10
6
UV/
visible
absorption
spectrum
NA
Product
Chemistry
Chapter
of
the
Tolerance
Reassessment
Eligibility
Decision
(
TRED)

B.
EXPERIMENTAL
DESIGN
B.
1.
Study
Site
Information
Mustard
Greens
were
grown
and
maintained
at
each
trial
site
using
typical
agricultural
practices
for
the
respective
geographical
region
(
Table
B.
1.1).
Monthly
rainfall
and
irrigation
data
were
provided
for
each
site,
along
with
10­
to
30­
year
average
rainfall
data.
No
detailed
temperature
data
were
reported
for
any
site.
Information
was
also
provided
on
maintenance
chemicals
and
other
pesticides
used
at
each
site.
Variations
from
historical
values
in
temperature
were
cited
at
TN01,
where
it
was
cool
in
the
early
growing
season
and
CA16
where
weather
was
warmer
than
usual.

TABLE
B.
1.1.
Trial
Site
Conditions.
Soil
characteristics1
Trial
Identification
(
City,
State;
Year)
Type
%
OM
pH
CEC
(
meq/
g)
Gainesville,
FL;
1999
Sand
2.6­
2.8
5.9­
6.0
Tifton,
GA;
1999
Sand
0.67
6.0
Tifton,
GA;
1999
Loamy
sand
0.67
6.2
Crossville,
TN;
1999
Loam
2.67
5.3
Weslaco,
TX;
1999
Sandy
Clay
Loam
0.5
8.0
N.
Leeds,
WI;
1999
Silt
Loam
4.4
5.9
Parlier,
CA;
1999
Fine
sandy
loam
0.44
6.4
Holtville,
CA;
1999
Silty
Clay
Loam
0.87
7.4
NR
1
OM
=
Organic
matter,
CEC
=
Cation­
exchange
capacity.
These
parameters
are
optional
except
in
cases
where
their
value
affects
the
use
pattern
for
the
chemical.
NR
=
Not
reported
Bifenthrin/
128825/
IR­
4
DACO
7.4.1/
7.4.2/
OPPTS
860.1500/
OECD
IIA
6.3.1,
6.3.2,
6.3.3
and
IIIA
8.3.1,
8.3.2,
8.3.3
Crop
Field
Trial
 
Mustard
Greens
DP#:
310089/
MRID#:
45660301
Page
4
of
8
TABLE
B.
1.2.
Study
Use
Pattern.
Application
Location
(
City,
State;
Year)
Trial
ID
EP1
Method;
Timing
Volume
(
Gal/
A)
Single
Rate
(
lb
ai/
A)
RTI2
(
days)
Total
Rate
(
lb
ai/
A)
Tank
Mix/
Adjuvants
31
0.104
­­­
32
0.107
7
31
0.106
7
Gainesville,
FL;
1999
06970.99­
FL21
2
lb/
gal
EC
Directed
Foliar;
Vegetative
32
0.110
7
0.427
None
50
0.100
­­­
50
0.100
7
50
0.101
7
Tifton,
GA;
1999
06970.99­
GA*
04
2
lb/
gal
EC
Directed
Foliar;
Vegetative
50
0.101
7
0.402
None
51
0.102
­­­
51
0.102
7
50
0.100
7
Tifton,
GA;
1999
06970.99­
GA*
05
2
lb/
gal
EC
Directed
Foliar;
Vegetative
50
0.101
7
0.405
None
28
0.104
­­­
28
0.103
6
28
0.104
7
Crossville,
TN;
1999
06970.99­
TN01
2
lb/
gal
EC
Broadcast
Foliar;
Vegetative
27
0.101
7
0.412
None
40
0.099
­­­
43
0.100
7
43
0.100
8
Weslaco,
TX;
1999
06970.99­
TX06
2
lb/
gal
EC
Broadcast
Foliar;
Vegetative
47
0.101
6
0.400
None
26
0.099
­­­
26
0.097
7
25
0.100
6
N.
Leeds,
WI;
1999
06970.99­
WI03
2
lb/
gal
EC
Broadcast
Foliar;
Vegetative
25
0.101
6
0.397
None
32
0.101
­­­
31
0.101
6
31
0.104
8
Parlier,
CA;
1999
06970.99­
CA15
2
lb/
gal
EC
Directed
Foliar;
Vegetative
31
0.103
7
0.409
None
32
0.099
­­­
33
0.101
8
32
0.099
8
Holtville,
CA;
1999
06970.99­
CA16
2
lb/
gal
EC
Directed
Foliar;
Vegetative
33
0.102
6
0.401
None
1
EP
=
End­
use
Product
2
RTI
=
Retreatment
Interval
Bifenthrin/
128825/
IR­
4
DACO
7.4.1/
7.4.2/
OPPTS
860.1500/
OECD
IIA
6.3.1,
6.3.2,
6.3.3
and
IIIA
8.3.1,
8.3.2,
8.3.3
Crop
Field
Trial
 
Mustard
Greens
DP#:
310089/
MRID#:
45660301
Page
5
of
8
TABLE
B.
1.3.
Trial
Numbers
and
Geographical
Locations.

Mustard
Greens
Requested
NAFTA
Growing
Region1
Submitted
Canada
US
2
2
NA
2
3
1
NA
1
4
1
NA
1
5
1
NA
1
6
1
NA
1
10
2
NA
2
Total
8
NA
8
1
Regions
13­
21
and
1A,
5A,
5B,
and
7A
were
not
included
as
the
use
is
for
the
US
only.
NA
=
not
applicable.

B.
2.
Sample
Handling
and
Preparation
Duplicate
control
and
treated
samples
of
mustard
greens
( 
12
plants)
were
harvested
from
each
trial
site
at
commercial
maturity,
6­
7
DAT.
Samples
were
placed
into
frozen
storage
within
1.5
hours
of
sampling.
Samples
were
shipped
frozen
by
ACDS
freezer
truck
to
the
analytical
laboratory,
where
samples
were
stored
at
­
26
to
­
10
°
C
until
extraction
for
analysis.

B.
3.
Analytical
Methodology
Samples
of
mustard
greens
were
analyzed
for
residues
of
bifenthrin
using
a
modification
of
the
GC/
ECD
enforcement
method
titled
"
Analytical
method
for
the
determination
of
bifenthrin
in/
on
various
crops
and
soils"
(
FMC
Corporation
Method
P­
2132M).
A
Dionex
ASE­
200
automated
extraction
was
used
instead
of
the
extraction
procedures
specified
in
the
method
in
order
to
speed
sample
preparation.

Briefly,
residues
were
extracted
using
the
Dionex
ASE­
200
instrumentation,
which
extracts
residues
with
hexane
at
high
pressures
(
2000
lb/
inch2)
and
temperatures
(
90
°
C).
Following
automated
extraction
of
residues,
the
extract
solvent
was
removed
by
rotary
evaporation.
Residues
were
then
redissolved
in
hexane
for
analysis.
Residue
levels
of
bifenthrin
were
determined
by
GC/
ECD;
external
standards
were
used
for
quantitation.
The
validated
method
LOQ
for
bifenthrin
in/
on
mustard
greens
is
0.05
ppm;
an
LOD
was
not
reported.

Prior
to
analysis
of
field
trial
samples,
the
method
was
validated
using
control
samples
of
mustard
greens
fortified
with
bifenthrin
at
0.051,
0.51,
2.03,
and
6.10
ppm.
The
method
was
also
validated
concurrently
with
the
analysis
of
field
trial
samples.

C.
RESULTS
AND
DISCUSSION
The
number
and
geographic
representation
of
the
mustard
green
field
trials
are
adequate.
In
eight
field
trials
conducted
during
1999,
bifenthrin
(
EC)
was
applied
as
four
broadcast
foliar
applications
to
mustard
greens
at
0.097­
0.110
lb
ai/
A/
application,
for
a
total
of
0.397­
0.4.27
lb
Bifenthrin/
128825/
IR­
4
DACO
7.4.1/
7.4.2/
OPPTS
860.1500/
OECD
IIA
6.3.1,
6.3.2,
6.3.3
and
IIIA
8.3.1,
8.3.2,
8.3.3
Crop
Field
Trial
 
Mustard
Greens
DP#:
310089/
MRID#:
45660301
Page
6
of
8
ai/
A/
season,
at
RTIs
of
6­
8
days.
At
commercial
maturity
(
6­
7
DAT),
duplicate
control
and
treated
samples
of
fresh
mustard
greens
were
collected
from
each
trial.

The
GC/
ECD
method
used
to
determine
bifenthrin
residues
in/
on
mustard
greens
was
adequately
validated
prior
to
and
in
conjunction
with
the
field
sample
analyses.
Method
validation
recoveries
from
control
samples
fortified
at
0.05­
6.10
ppm
averaged
73­
104%
with
standard
deviations
2­
8%
(
Table
C.
1),
and
concurrent
method
recoveries
of
bifenthrin
average
101
±
15%
from
greens
fortified
at
0.05
ppm.
Apparent
residues
of
bifenthrin
were
<
LOQ
in/
on
all
16
control
samples.
The
validated
method
LOQ
for
bifenthrin
in
mustard
greens
is
0.05
ppm,
and
the
LOD
was
not
reported.
Adequate
sample
calculations
and
example
chromatograms
were
provided.

The
samples
were
stored
frozen
from
collection
to
analysis
for
up
to
65
days
(
Table
C.
2).
Storage
stability
data
are
not
available
for
mustard
greens;
however,
storage
stability
data
are
available
indicating
that
bifenthrin
is
stable
for
up
to
36
months
in
frozen
lettuce
(
Memo,
S.
Levy,
21­
AUG­
2002;
DP#:
283808).
These
data
will
support
the
storage
intervals
and
conditions
of
the
mustard
green
field
trials.

Bifenthrin
residues
were
0.05­
2.05
ppm
in/
on
16
samples
of
mustard
greens
harvested
6­
7
DAT
(
Table
C.
3).
The
average
and
HAFT
residues
in/
on
mustard
greens
were
1.04
and
2.01
ppm,
respectively
(
Table
C.
4).
Residue
decline
data
were
not
provided.

TABLE
C.
1.
Summary
of
Method
Recoveries
of
Bifenthrin
from
Mustard
Greens.
Analyte
Matrix
Spike
level
(
ppm)
Sample
size
(
n)
Recoveries
(%)
Mean
"
std
dev
(%)
Method
Validation
Recoveries
0.051
3
66­
82
(
1)
1
73
±
8
0.51
3
84­
96
88
±
7
2.03
3
102­
106
104
±
2
Bifenthrin
Mustard
greens
6.10
3
89­
97
92
±
4
Concurrent
method
recoveries
Bifenthrin
Mustard
Greens
0.051
8
79­
119
101
±
15
1
The
number
of
recoveries
outside
the
70­
120%
range
is
indicated
in
parentheses.

TABLE
C.
2.
Summary
of
Storage
Conditions.
Matrix
Storage
Temperature
(
°
C)
Actual
Storage
Duration
(
days)
Interval
of
Demonstrated
Storage
Stability
(
months)
1
Mustard
Greens
­
26
to­
10
°
C
65
36
1
Bifenthrin
TRED,
S.
Levy,
21­
AUG­
2002;
DP#:
283808.
Bifenthrin/
128825/
IR­
4
DACO
7.4.1/
7.4.2/
OPPTS
860.1500/
OECD
IIA
6.3.1,
6.3.2,
6.3.3
and
IIIA
8.3.1,
8.3.2,
8.3.3
Crop
Field
Trial
 
Mustard
Greens
DP#:
310089/
MRID#:
45660301
Page
7
of
8
TABLE
C.
3.
Residue
Data
from
Mustard
Green
Field
Trials
using
Bifenthrin
(
2
lb/
gal
EC).
Trial
ID
(
City,
State;
Year)
Zone
Variety
Commodity
or
Matrix
Total
Rate
(
lb
ai/
A)
PHI
(
days)
Bifenthrin
residues
(
ppm)
Gainesville,
FL;
1999
06970.99­
FL21
3
Florida
Broadleaf
Leaves
0.427
7
1.85,
1.71
Tifton,
GA;
1999
06970.99­
GA*
04
2
Southern
Giant
Curled
Leaves
0.402
7
2.05,
1.97
Tifton,
GA;
1999
06970.99­
GA*
05
2
Southern
Giant
Curled
Leaves
0.405
7
1.39,
1.17
Crossville,
TN;
1999
06970.99­
TN01
4
Southern
Giant
Curled
Leaves
0.412
7
0.75,
0.91
Weslaco,
TX;
1999
06970.99­
TX06
6
Florida
Broadleaf
Leaves
0.400
7
0.05,
0.08
N.
Leeds,
WI;
1999
06970.99­
WI03
5
Southern
Giant
Curled
Leaves
0.397
7
0.18,
0.19
Parlier,
CA;
1999
06970.99­
CA15
10
Florida
Broadleaf
Leaves
0.409
7
1.90,
1.45
Holtville,
CA;
1999
06970.99­
CA16
10
Tendergreen
Leaves
0.401
6
0.85,
0.84
TABLE
C.
4.
Summary
of
Residue
Data
from
Mustard
Green
Field
Trials
with
Bifenthrin
(
EC).
Residue
Levels
(
ppm)
Commodity
Total
Applic.
Rate
(
lb
ai/
A)
PHI
(
days)
n
Min.
Max.
HAFT1
Median
Mean
Std.
Dev.

Mustard
Greens
0.397­
0.427
6­
7
16
0.05
2.05
2.01
1.04
1.08
0.71
1
HAFT
=
Highest­
Average
Field
Trial.

D.
CONCLUSION
The
mustard
green
field
trial
data
are
adequate
and
will
support
the
use
of
up
to
four
foliar
applications
of
bifenthrin
(
EC)
at
0.1
lb
ai/
A/
application
for
a
maximum
seasonal
rate
of
0.4
lb
ai/
A.

E.
REFERENCES
DP#:
283808
Subject:
Bifenthrin.
Residue
and
Product
Chemistry
Considerations
for
the
Tolerance
Reassessment
Eligibility
Decision
(
TRED)
From:
S.
Levy
To:
T.
Myers
Dated:
21­
AUG­
2002
MRID(
s):
None
Bifenthrin/
128825/
IR­
4
DACO
7.4.1/
7.4.2/
OPPTS
860.1500/
OECD
IIA
6.3.1,
6.3.2,
6.3.3
and
IIIA
8.3.1,
8.3.2,
8.3.3
Crop
Field
Trial
 
Mustard
Greens
DP#:
310089/
MRID#:
45660301
Page
8
of
8
F.
DOCUMENT
TRACKING
RDI:
RAB1
Chemists
(
16­
NOV­
2005)
Petition#:
2E6451
DP#:
310089
PC
Code:
128825
Template
Version
June
2005