Document ID: EPA-HQ-OPP-2006-0366-0009
Agency: epa
Document Type: Supporting & Related Material
Title: 
Posted Date: 2006-08-11T04:00Z

Bifenthrin/
128825/
IR­
4
DACO
7.4.1/
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
­
Cilantro
DP#:
310089/
MRID#:
46279701
Page
1
of
7
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
Rd.,
Building
100,
Suite
B;
Durham,
NC
27713;
submitted
20­
APR­
2005).
The
DER
has
been
reviewed
by
the
HED
and
revised
to
reflect
current
Office
of
Pesticide
Programs
(
OPP)
policies.

STUDY
REPORT:

46279701
Samoil,
K.
(
2004)
Bifenthrin:
Magnitude
of
the
Residue
on
Cilantro.
Lab
Project
Number:
07557.
Unpublished
study
prepared
by
IR­
4
Project,
The
Technology
Center
of
New
Jersey.
141
p.

EXECUTIVE
SUMMARY:

Field
trials
on
cilantro
were
conducted
at
four
trial
sites
in
CA
(
2),
GA
(
1),
and
TX
(
1)
during
2000­
2001.
Bifenthrin
(
2
lb/
gal
EC)
was
applied
as
five
broadcast
foliar
applications
to
cilantro
at
0.097­
0.106
lb
ai/
A/
application,
for
a
total
of
0.497­
0.518
lb
ai/
A/
season.
Applications
were
made
beginning
at
the
1­
4
true
leaf
stage,
at
retreatment
intervals
(
RTIs)
of
6­
7
days.
At
commercial
maturity,
samples
of
fresh
cilantro
foliage
(
3
trials)
and
seeds
(
1
trial)
were
harvested
at
3
day
pre­
harvest
intervals
(
PHIs).
At
one
of
the
trial
sites,
additional
samples
of
fresh
cilantro
were
harvested
at
a
2­
day
PHI
and
dried
in
ovens
for
2
days
to
yield
dried
cilantro
samples.
Duplicate
control
and
treated
samples
were
collected
for
analysis
from
each
trial.
Samples
were
stored
frozen
for
up
to
23
months,
an
interval
supported
by
the
available
storage
stability
data.

The
gas
chromatography
(
GC)/
electron­
capture
detector
(
ECD)
method
used
to
determine
bifenthrin
residues
in/
on
cilantro
(
FMC
Corporation
Report
No.
P­
2132M,
modified)
was
adequately
validated
in
conjunction
with
the
field
trial
analyses.
Briefly,
bifenthrin
residues
are
extracted
with
hexane,
concentrated,
and
cleaned
up
using
a
Florisil
column.
The
residues
were
analyzed
by
GC/
ECD
using
a
capillary
DB­
1
column.
The
validated
limit
of
quantitation
(
LOQ)
was
0.05
ppm;
and
the
calculated
LOQ
for
bifenthrin
in/
on
fresh
cilantro,
dry
cilantro,
and
cilantro
seeds
are
0.026,
0.106,
and
0.071
ppm,
respectively.
The
calculated
limit
of
detection
(
LOD)
for
bifenthrin
in/
on
fresh
cilantro,
dry
cilantro,
and
cilantro
seeds
are
0.026,
0.106,
and
0.071
ppm,
respectively.

Bifenthrin
residues
were
1.98­
4.83
ppm
in/
on
6
samples
of
fresh
cilantro
foliage
harvested
at
a
3­
day
PHI,
14.93­
16.25
ppm
in/
on
2
dried
cilantro
samples
harvested
at
a
2­
day
PHI,
and
3.66­
3.69
ppm
in/
on
2
cilantro
seed
samples
harvested
at
a
3­
day
PHI.
The
average
and
highest­
average
field
trial
(
HAFT)
residues
in/
on
fresh
cilantro
were
2.97
and
3.96
ppm,
respectively.
Based
on
average
residues
in
fresh
cilantro
(
2.73
ppm)
and
dried
cilantro
(
15.59
ppm)
from
one
trial,
the
concentration
factor
for
dried
cilantro
is
5.7x.
Bifenthrin/
128825/
IR­
4
DACO
7.4.1/
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
­
Cilantro
DP#:
310089/
MRID#:
46279701
Page
2
of
7
O
O
Cl
F
3
C
CH
3
CH
3
C
H
3
STUDY/
WAIVER
ACCEPTABILITY/
DEFICIENCIES/
CLARIFICATIONS:

Under
the
conditions
and
parameters
used
in
the
study,
the
cilantro
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].

COMPLIANCE:

Signed
and
dated
Good
Laboratory
Practice
(
GLP),
quality
assurance,
and
data
confidentiality
statements
were
provided.
No
deviations
from
regulatory
requirements
were
noted
that
would
impact
the
study
results
or
their
interpretation.

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
emulsifiable
concentrate
(
EC)
and
is
marketed
by
FMC
Corporation
as
Capture
®
2
EC.

TABLE
A.
1.
Nomenclature
of
Test
Compound.

Compound
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
Bifenthrin/
128825/
IR­
4
DACO
7.4.1/
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
­
Cilantro
DP#:
310089/
MRID#:
46279701
Page
3
of
7
TABLE
A.
2.
Physicochemical
Properties
of
the
Technical
Grade
Bifenthrin.

Parameter
Value
Reference
Melting
point/
range
68­
70.6
/

C
Product
Chemistry
Chapter
of
the
Tolerance
Reassessment
Eligibility
Decision
(
TRED)
pH
NA
Density
at
24
/

C
1.26
g/
mL
Water
solubility
<
0.1
µ
g/
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
NA
=
not
available
B.
EXPERIMENTAL
DESIGN
B.
1.
Study
Site
Information
TABLE
B.
1.1.
Trial
Site
Conditions.

Trial
Identification
(
City,
State;
Year)
Soil
characteristics1
Meteorological
data
Type
%
OM
pH
CEC
Total
rainfall
(
inches)
2
Overall
temperature
range
(
°
C)

Cilantro
Waslaco,
TX;
2000
Sandy
loam
0.5
7.9
NR
5.37
22­
27
Salinas,
CA;
2001
Loam
NR
7.5
NR
4.50
19­
25
Salinas,
CA;
2001
Loam
NR
7.5
NR
0.49
7­
16
Tifton,
GA;
2001
Sand
0.67
6.2
NR
3.74
24­
30
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.
2
Total
rainfall
and
irrigation
provided
from
first
to
last
applications.
NR
=
Not
reported
A
summary
of
weather
conditions
was
provided
for
each
field
site,
including
temperature
range
and
total
precipitation/
irrigation
during
the
field
trial
(
Table
B.
1.1).
No
unusual
conditions
were
reported
that
would
affect
the
integrity
of
the
study.
The
use
pattern
in
each
field
trial
are
present
below
in
Table
B.
1.2.
Bifenthrin/
128825/
IR­
4
DACO
7.4.1/
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
­
Cilantro
DP#:
310089/
MRID#:
46279701
Page
4
of
7
TABLE
B.
1.2.
Study
Use
Pattern
on
Cilantro.

Location
(
City,
State;
Year)
Application
EP1
Method2;
Timing3
Volume
(
gal/
A)
Single
Rate
(
lb
ai/
A)
4
No.
of
Appl.
RTI
(
days)
Total
Rate
(
lb
ai/
A)
4
Tank
Mix
Adjuvants
Waslaco,
TX;
2000
2.0
lb/
gal
EC
Directed
foliar;
vegetative
stage
39­
44
0.099­
0.104
5
7
0.506
None
Salinas,
CA;
2001
2.0
lb/
gal
EC
Directed
and
broadcast
foliar;
vegetative
stage
58­
75
0.097­
0.101
5
7
0.497
None
Salinas,
CA;
2001
2.0
lb/
gal
EC
Broadcast
foliar;
vegetative
stage
88­
92
0.102­
0.106
5
6­
7
0.518
None
Tifton,
GA;
2001
2.0
lb/
gal
EC
Directed
foliar;
vegetative
stage
50­
51
0.101­
0.102
5
6­
7
0.508
None
1
EP
=
End­
use
Product.
2
All
applications
were
made
using
ground
equipment.
3
The
first
applications
were
made
beginning
at
the
1­
4
true
leaf
stage,
with
subsequent
applications
made
during
the
vegetative
and
flowering
stages.
4
The
single
target
rate
was
0.10
lb
ai/
A
and
the
total
target
rate
was
0.50
lb
ai/
A.

TABLE
B.
1.3.
Trial
Numbers
and
Geographical
Locations.

NAFTA
Growing
Region1
Cilantro
Submitted
Requested2
Canada
US
2
1
NA
­­

6
1
NA
­­

10
2
NA
­­

Total
4
NA
­­

1
Regions
13­
21
and
1A,
5A,
5B,
and
7A
were
not
included
as
the
use
is
for
the
US
only.
2
There
are
no
cilantro
field
location
requirements.
NA
=
not
applicable.

B.
2.
Sample
Handling
and
Preparation
Duplicate
control
and
treated
samples
(
1­
2
lbs)
of
fresh
cilantro
were
harvested
at
a
3­
day
PHI
from
3
of
the
4
trials,
and
duplicate
control
and
treated
samples
of
seeds
were
harvested
at
a
3­
day
PHI
from
the
fourth
trial.
In
addition,
control
and
treated
bulk
samples
(
21
lb)
of
fresh
cilantro
samples
were
collected
from
one
of
the
trials
at
a
2­
day
PHI
and
placed
in
drying
ovens
for
2
days,
after
which
duplicate
control
and
treated
samples
of
dried
cilantro
were
collected.
All
samples
were
placed
in
frozen
storage
(<
0
°
C)
within
4
hours
of
collection
and
shipped
frozen
to
the
analytical
laboratory
(
North
Central
Region
Leader
Laboratory,
Michigan
State
University,
East
Lansing),
where
samples
were
stored
at
­
28
to
­
4
°
C
until
analysis.
Samples
were
stored
frozen
from
collection
to
analysis
for
658,
678,
and
504
days
for
fresh
cilantro,
dry
cilantro,
and
seeds,
respectively.

B.
3.
Analytical
Methodology
Bifenthrin/
128825/
IR­
4
DACO
7.4.1/
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
­
Cilantro
DP#:
310089/
MRID#:
46279701
Page
5
of
7
A
GC/
ECD
method
entitled
"
Analytical
method
for
the
determination
of
bifenthrin
in/
on
various
crops
and
soils"
(
Modified
FMC
Corporation
Report
No.
P­
2132M)
has
been
validated
by
the
Agency.
A
brief
description
of
the
method
follows.

Briefly,
bifenthrin
residues
are
extracted
with
hexane,
concentrated,
and
cleaned
up
using
a
Florisil
column.
The
residues
were
analyzed
by
GC/
ECD
using
a
capillary
DB­
1
column.
The
estimated
LOQ
was
0.05
ppm.

C.
RESULTS
AND
DISCUSSION
The
number
and
geographic
representation
of
the
cilantro
field
trials
are
adequate.
In
four
field
trials
conducted
during
2000­
2001,
bifenthrin
(
EC)
was
applied
as
five
broadcast
foliar
applications
to
cilantro
at
0.097­
0.106
lb
ai/
A/
application,
for
a
total
of
0.497­
0.518
lb
ai/
A/
season,
at
RTIs
of
6­
7
days.
At
commercial
maturity
(
3­
day
PHI),
fresh
cilantro
foliage
was
collected
from
3
trials
and
seeds
were
collected
from
the
fourth
trial.
Additional
samples
for
fresh
cilantro
were
collected
from
one
of
the
trials
at
a
2­
day
PHI
and
dried
in
ovens
to
yield
samples
of
dried
cilantro.
Duplicate
control
and
treated
samples
were
collected
for
analysis
from
each
trial.

The
fresh
and
dried
foliage
and
seed
samples
were
stored
frozen
from
collection
to
analysis
for
up
to
approximately
22,
23,
and
17
months,
respectively
(
Table
C.
2).
Storage
stability
data
are
not
available
for
cilantro;
however,
available
stability
data
indicate
that
bifenthrin
is
stable
for
up
to
36
months
in/
on
lettuce
(
Memo,
S.
Levy,
21­
AUG­
2002;
DP#:
283808).

The
GC/
ECD
method
(
Modified
FMC
Corporation
Report
No.
P­
2132M)
used
to
determine
bifenthrin
residues
in/
on
cilantro
is
adequate
for
data
collection.
Average
method
validation
recoveries
were
91
±
4%
from
9
fresh
cilantro
samples
fortified
at
0.05­
4.88
ppm,
81
±
12%
from
12
dry
cilantro
samples
fortified
at
0.10­
20.03
ppm,
and
92
±
15%
from
12
seed
samples
fortified
at
0.05­
4.91
ppm
(
Table
C.
1).
The
average
concurrent
method
recoveries
were
79
±
9%
from
9
fresh
cilantro
samples
fortified
at
0.248­
1.00
ppm,
76%
from
the
one
dry
cilantro
sample
fortified
at
4.948
ppm,
and
71%
from
the
one
seed
sample
fortified
at
0.409
ppm.
Apparent
residues
of
bifenthrin
were
<
LOQ
(<
0.05)
in/
on
all
control
samples.
The
estimated
LOQ
was
0.05
ppm;
and
the
calculated
LOQ
for
bifenthrin
in/
on
fresh
cilantro,
dry
cilantro,
and
cilantro
seeds
are
0.026,
0.106,
and
0.071
ppm,
respectively.
The
calculated
LOD
for
bifenthrin
in/
on
fresh
cilantro,
dry
cilantro,
and
cilantro
seeds
are
0.026,
0.106,
and
0.071
ppm,
respectively.
Adequate
sample
calculations
and
chromatograms
were
provided.

Following
the
last
of
five
foliar
applications
of
bifenthrin
totaling
0.497­
0.518
lb
ai/
A
(
1x),
bifenthrin
residues
were
1.98­
4.83
ppm
in/
on
6
samples
of
fresh
cilantro
harvested
at
a
3­
day
PHI,
14.93­
16.25
ppm
in/
on
2
dried
cilantro
samples
harvested
at
a
2­
day
PHI,
and
3.66­
3.69
ppm
in/
on
2
cilantro
seed
samples
harvested
at
a
3­
day
PHI
(
Table
C.
3).
Average
residues
in/
on
fresh
cilantro
were
2.97
ppm
(
Table
C.
4),
and
HAFT
residues
were
3.96
ppm.
Based
on
average
residues
in
fresh
cilantro
(
2.73
ppm)
and
dried
cilantro
(
15.59
ppm)
from
one
trial,
the
concentration
factor
for
dried
cilantro
is
5.7x.
Bifenthrin/
128825/
IR­
4
DACO
7.4.1/
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
­
Cilantro
DP#:
310089/
MRID#:
46279701
Page
6
of
7
Common
cultural
practices
were
used
to
maintain
plants,
and
the
weather
conditions
and
the
maintenance
chemicals
and
fertilizer
used
in
the
study
did
not
have
a
notable
impact
on
the
residue
data.

TABLE
C.
1.
Summary
of
Method
Validation
and
Concurrent
Recovery
Results
using
GC/
ECD
Method
P­
2132M
for
Cilantro.

Analyte
Matrix
Spiking
Level
(
mg/
kg)
Sample
size
Recoveries
(%)
Mean
Recovery
±
SD
Method
Validation
Recoveries
Bifenthrin
Fresh
Cilantro
0.05
3
82­
90
91
±
4
0.50
3
92­
98
4.87­
4.88
3
89­
93
Dried
Cilantro
0.10
6
66­
98
81
±
12
0.99­
1.00
3
64­
83
4.97­
4.99
3
83­
107
19.95­
20.03
3
76­
79
Seeds
0.05
6
79­
116
92
±
15
0.41
3
88­
98
4.91
3
69­
89
Concurrent
Method
Recoveries
Bifenthrin
Fresh
Cilantro
0.248
1
69
79
±
9
0.509
1
86
1.00
1
81
Dried
Cilantro
4.948
1
76
76
Seeds
0.409
1
71
71
TABLE
C.
2.
Summary
of
Freezer
Storage
Conditions.

Matrix
Storage
Temp.
(/
C)
Actual
Storage
Duration
(
months)
1
Limit
of
Demonstrated
Storage
Stability
(
months)
2
Fresh
Cilantro
<
­
28
to
­
4
~
22
362
Dry
Cilantro
~
23
Seeds
~
17
1
Extracts
were
stored
frozen
for
2­
8
days
prior
to
analysis.
2
Storage
stability
data
are
not
available
for
cilantro;
however,
available
stability
data
indicate
that
bifenthrin
is
stable
for
up
to
36
months
in/
on
lettuce
(
Memo,
S.
Levy,
21­
AUG­
2002;
DP#:
283808).

TABLE
C.
3.1.
Residue
Data
from
Cilantro
Field
Trials
with
Bifenthrin,
as
2.0
lb
ai/
gal
EC.

Trial
ID
(
City,
State;
Year)
EPA
Region
Variety
Cilantro
Matrix
Total
Rate
(
lb
ai/
A)
PHI
(
days)
Bifenthrin
Residues
(
ppm)
1
Waslaco,
TX;
2000
6
Santo
Fresh
Cilantro
0.506
3
1.98,
2.44
Salinas,
CA;
2001
10
NR
Fresh
Cilantro
0.497
3
2.84,
2.61
(
2.73)
2
Dry
Cilantro
2
14.93,
16.25
(
15.59)
2
Salinas,
CA;
2001
10
NR
Seed
0.518
3
3.66,
3.69
Tifton,
GA;
2001
2
Jantar
Fresh
Cilantro
0.508
3
4.83,
3.09
Bifenthrin/
128825/
IR­
4
DACO
7.4.1/
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
­
Cilantro
DP#:
310089/
MRID#:
46279701
Page
7
of
7
1
The
estimated
LOQ
was
0.05
ppm;
and
the
calculated
LOQ
for
bifenthrin
in/
on
fresh
cilantro,
dry
cilantro,
and
cilantro
seeds
are
0.026,
0.106,
and
0.071
ppm,
respectively.
The
calculated
LOD
for
bifenthrin
in/
on
fresh
cilantro,
dry
cilantro,
and
cilantro
seeds
are
0.026,
0.106,
and
0.071
ppm,
respectively.
2
For
comparison,
average
residue
for
fresh
and
dried
cilantro
from
the
same
trial
are
listed
in
parentheses.
NR
=
Not
reported
TABLE
C.
4.
Summary
of
Residue
Data
for
Cilantro
from
Crop
Field
Trials
using
Bifenthrin.

Commodity
Formulation
Total
Rate
(
lb
ai/
A)
PHI
(
days)
Residue
Levels
(
ppm)
1
n
Min.
Max.
HAFT2
Median
Mean
Std.
Dev.

Fresh
Cilantro
2.0
lb/
gal
EC
0.497­
0.508
3
6
1.98
4.83
3.96
2.73
2.97
0.99
Dry
Cilantro
2.0
lb/
gal
EC
0.497
2
2
14.93
16.25
NA
15.60
15.59
0.94
Seeds
2.0
lb/
gal
EC
0.518
3
2
3.66
3.69
NA
3.67
3.67
0.03
1
The
estimated
LOQ
is
0.05
ppm
for
bifenthrin
in/
on
cilantro.
For
calculation
of
the
median,
mean,
and
standard
deviation,
½
LOQ
was
used
for
samples
with
residues
<
LOQ.
2
HAFT
=
Highest­
Average
Field
Trial.
NA=
Not
applicable
D.
CONCLUSION
The
cilantro
field
trial
data
are
adequate
and
will
support
the
use
of
up
to
five
foliar
applications
of
bifenthrin
(
EC)
at
0.1
lb
ai/
A/
application
for
a
maximum
seasonal
rate
of
0.5
lb
ai/
A.

E.
REFERENCES
DP#:
283808
Subject:
Bifenthrin
(
PC
Code:
128825).
Residue
and
Product
Chemistry
Considerations
for
the
Tolerance
Reassessment
Eligibility
Decision
(
TRED).
From:
S.
Levy
To:
T.
Myers
Dated:
21­
AUG­
2002
MRID(
s):
NR
F.
DOCUMENT
TRACKING
RDI:
RAB1
Chemists
(
16­
NOV­
2005)
Petition#:
4E6843
DP#:
310089
PC
Code:
128825
Template
Version
September
2003