Page
1of
21
UNITED
STATES
ENVIRONMENTAL
PROTECTION
AGENCY
WASHINGTON,
D.
C.
20460
OFFICE
OF
PREVENTION,
PESTICIDES
AND
TOXIC
SUBSTANCES
MEMORANDUM
Date:
06­
APR­
2006
Subject:
Bifenthrin.
Petitions
for
Tolerances
and
Uses
on
Tuberous
and
Corm
Vegetables
(
Subgroup
1C;
PP#
3E6882),
Leafy
Brassica
Greens
(
Subgroup
5B;
2E6451),
Dried
Shelled
Peas
and
Beans
(
Subgroup
6C;
2E6423),
and
Cilantro
(
4E6843),
and
a
Label
Amendment
for
Use
on
Tobacco.
Summary
of
Analytical
Chemistry
and
Residue
Data.

DP#
s:
310089,
310874,
313738,
313817,
313299,
317208
Decision#
s:
305246,
305406,
327616,
331702,
351451,
351522
PC
Code:
128825
MRID#
s:
45624701,
45660301,
45794202,
45794203,
46045001,
46279701
40
CFR
180.442
Chemical
Class:
Synthetic
Pyrethroid
From:
Sarah
J.
Levy,
M.
S.,
Chemist
George
F.
Kramer,
Ph.
D.,
Chemist
Registration
Branch
1
(
RAB1)
Health
Effects
Division
(
HED;
7509C)

Through:
P.
V.
Shah,
Ph.
D.,
Branch
Senior
Scientist
RAB1/
HED
(
7509C)

To:
George
LaRocca,
PM
13
Insecticide
Branch
Registration
Division
(
RD;
7505C)

This
document
was
originally
prepared
under
contract
by
Dynamac
Corporation
(
1910
Sedwick
Rd.,
Building
100,
Suite
B;
Durham,
NC
27713;
submitted
25­
OCT­
2005).
The
document
has
been
reviewed
by
the
HED
and
revised
to
reflect
current
OPP
policies.

Executive
Summary
Bifenthrin
(
2­
methyl[
1,1'­
biphenyl]
3­
yl)
methyl­
3­(
2­
chloro­
3,3,3­
trifluoro­
1­
propenyl)­
2,2­
dimethyl­
cyclopropanecarboxylate)
is
a
synthetic
pyrethroid
that
is
currently
used
for
control
of
insects
on
a
variety
of
fruit,
vegetable
and
field
crops.
Permanent
tolerances
are
established
for
residues
of
bifenthrin
in/
on
plant
and
livestock
commodities
at
levels
ranging
from
0.05
ppm
(
limit
of
quantitation
(
LOQ))
on
various
commodities
to
10.0
ppm
in/
on
dried
hop
cones
[
40
CFR
§
180.442(
a)].

The
Interregional
Research
Project
No.
4
(
IR­
4)
has
submitted
a
series
of
petitions
(
PP#
s:
2E6451,
2E6423,
3E6882
and
4E6843)
proposing
the
use
of
bifenthrin,
formulated
as
a
2
lb/
gal
Summary
of
Analytical
Chemistr
y
and
Residue
Data
Bi
fenthrin
DP#
s
:
310089,
310874,
313738,
313817,
313299,
and
317208
Page
2
of
21
emulsifiable
concentrate
(
EC)
or
a
1.15%
granule
(
G),
on
tuberous
and
corm
vegetables,
Brassica
leafy
greens,
dried
shelled
peas
and
beans
(
except
soybeans),
and
cilantro.
The
proposed
use
for
tuberous
and
corm
vegetables
includes
an
at­
planting
application
of
the
EC
or
G
formulations
at
0.3
lb
ai/
A,
followed
by
up
to
two
foliar
applications
of
the
EC
formulation
at
0.1
lb
ai/
A/
application,
with
a
retreatment
interval
(
RTI)
of
21
days
and
a
21­
day
pre­
harvest
interval
(
PHI).
The
uses
on
Brassica
leafy
greens,
dried
peas
and
beans,
and
cilantro
(
coriander)
are
for
2
to
5
broadcast
foliar
applications
of
the
EC
formulation
at
0.1
lb
ai/
A/
application,
with
a
RTI
of
7
days
(
when
specified)
and
PHIs
of
3­
14
days.
In
conjunction
with
these
uses,
IR­
4
is
proposing
tolerances
for
residues
on
tuberous
and
corm
vegetables
(
subgroup
1C)
at
0.1
ppm,
Brassica
leafy
greens
(
subgroup
5B)
at
3.0
ppm,
dried
shelled
pea
and
bean,
except
soybean,
(
subgroup
6C)
at
0.1
ppm,
cilantro
leaves
and
seed
at
5.0
ppm,
and
cilantro
dried
leaves
at
30.0
ppm.
FMC
Corporation
is
also
requesting
a
label
amendment
for
its
EC
formulation
allowing
use
of
bifenthrin
on
tobacco
as
a
pre­
plant
or
at­
transplanting
application
at
0.1
lb
ai/
A
followed
by
foliar
application(
s)
at
0.05
lb
ai/
A/
application.

Based
on
the
previously­
submitted
cotton,
corn,
apple,
hen,
and
goat
metabolism
data
and
the
currently­
submitted
potato
metabolism
study,
the
nature
of
bifenthrin
residues
in
plants
and
livestock
is
understood.
The
residue
of
concern
is
bifenthrin
per
se
in
both
primary
and
rotated
crop
commodities
and
in
livestock.

Adequate
gas
chromatography
(
GC)/
electron­
capture
detection
(
ECD)
methods
are
available
for
enforcing
tolerances
of
bifenthrin
in
plant
and
livestock
commodities.
The
available
methods
for
plant
commodities
generally
involve
extraction
of
the
sample
with
acetone,
partitioning
with
hexane,
purification
using
a
Florisil
column,
and
analysis
of
residues
by
GC/
ECD.
The
limit
of
quantitation
(
LOQ)
for
these
methods
is
0.05
ppm.
Samples
from
the
current
field
trials
and
the
potato
processing
study
were
analyzed
using
methods
that
are
modifications
to
one
of
the
current
enforcement
methods
(
P­
2550
M),
with
variations
in
extraction
solvents
and
detection
methods.
Residues
of
bifenthrin
in/
on
mustard
greens
and
cilantro
(
leaves
and
seeds)
were
determined
using
a
GC/
ECD
method
(
FMC
Report
P­
2132).
For
this
method,
residues
are
extracted
with
hexane,
concentrated,
and
cleaned
up
using
a
Florisil
column,
then
analyzed
by
GC/
ECD.
Residues
in/
on
potato
fractions
and
dried
beans
and
peas
were
determined
using
a
GC/
mass­
selective
detection
(
MSD)
method
(
FMC
Report
P­
3426).
For
this
method,
residues
are
extracted
with
acetone,
concentrated,
and
purified
by
silica­
gel
solid­
phase
extraction
(
SPE).
The
residues
are
then
analyzed
by
GC/
MSD,
using
the
m/
z
181
ion
for
quantitation.
Residues
in/
on
green
tobacco
were
determined
using
a
related
GC/
MSD
method
(
FMC
Report
P­
3457).
For
this
method,
residues
are
extracted
with
acetone/
water,
partitioned
into
hexane,
and
cleaned
up
with
a
SPE
column,
and
analyzed
by
GC/
MSD.
For
each
of
the
above
methods,
the
LOQ
for
bifenthrin
is
0.05
ppm,
and
the
reported
limit
of
detection
(
LOD)
is
0.01
ppm.
Each
of
these
methods
was
adequately
validated
in
conjunction
with
analysis
of
samples
from
the
field
trials
or
processing
study.

The
field
trials
on
potatoes,
mustard
greens,
dried
beans
and
peas,
cilantro,
and
tobacco
are
adequate.
An
adequate
number
of
trials
were
conducted
reflecting
the
proposed
use
patterns
in
the
appropriate
geographic
regions,
and
the
appropriate
commodities
were
collected
at
the
proposed
PHIs.
Samples
were
analyzed
using
adequate
analytical
methods,
and
the
sample
storage
intervals
are
supported
by
the
available
storage
stability
data.

Following
an
at­
planting
soil
application
and
two
foliar
applications
of
bifenthrin
at
1x
the
proposed
rate,
residues
were
<
0.05
ppm
(<
LOQ)
in/
on
all
potatoes
harvested
at
21
days
after
the
Summary
of
Analytical
Chemistr
y
and
Residue
Data
Bi
fenthrin
DP#
s
:
310089,
310874,
313738,
313817,
313299,
and
317208
Page
3
of
21
final
application
(
DAT).
Residues
on
mustard
greens
harvested
6­
7
DAT
were
<
0.05­
2.05
ppm
following
four
foliar
applications
of
bifenthrin
(
EC)
totaling
~
0.4
lb
ai/
A
(
1x).
In
the
dried
bean
and
pea
field
trials,
residues
on
dried
beans
harvested
13­
15
DAT
were
<
0.05­
0.10
ppm
following
three
foliar
applications
of
bifenthrin
(
EC)
totaling
0.3
lb
ai/
A
(
1x),
and
residues
on
dried
peas
harvested
14­
15
DAT
were
<
0.05
ppm
following
two
foliar
applications
of
bifenthrin
(
EC)
totaling
0.2
lb
ai/
A
(
1x).
Following
five
foliar
applications
of
bifenthrin
(
EC)
to
cilantro
totaling
~
0.5
lb
ai/
A
(
1x),
residues
at
3
DAT
were
1.98­
4.83
ppm
in/
on
fresh
leaves,
14.93­
16.25
ppm
in/
on
dried
leaves,
and
3.66­
3.69
ppm
in/
on
seeds.
In
the
tobacco
field
trials,
residues
of
bifenthrin
were
<
0.05
ppm
in/
on
all
green
tobacco
samples
harvested
at
normal
maturity
following
either
a
preplant
or
at­
transplanting
application
of
bifentrhin
(
EC
or
G)
at
0.1
lb
ai/
A
and
a
single
foliar
application
of
bifenthrin
(
EC)
at
0.05
or
0.10
lb
ai/
A
(
1x).

The
available
potato
processing
study
is
adequate.
Because
bifenthrin
residues
were
<
LOQ
(<
0.05
ppm)
in
all
samples
from
the
potato
field
trials
and
in
potato
tubers
and
all
processed
fractions
from
the
processing
study
conducted
at
a
3x
rate,
HED
concludes
that
residues
of
bifenthrin
in
wet
peel
are
unlikely
to
exceed
the
LOQ
when
bifenthrin
is
applied
at
a
1x
rate.
Therefore,
a
separate
tolerance
will
be
not
required
for
residues
in/
on
processed
potato
fractions.
In
addition,
a
comparison
of
residues
in/
on
fresh
and
dried
cilantro
leaves
indicates
that
there
is
a
5.7x
processing
factor
for
dried
cilantro
leaves.
Based
on
highest­
average
field­
trial
(
HAFT)
residues
of
3.96
ppm
in/
on
fresh
leaves,
the
maximum
expected
residues
in/
on
dried
cilantro
leaves
would
be
22.6
ppm.

The
proposed
tolerances
for
plant
commodities
will
not
have
any
impact
on
the
current
tolerances
for
livestock
commodities.
The
only
proposed
crop
use
with
any
regulated
livestock
feedstuffs
is
potato
(
processed
potato
waste
and
culls),
and
the
addition
of
these
commodities
to
livestock
diets
will
not
increase
the
dietary
exposure
of
livestock
calculated
in
the
Bifenthrin
Tolerance
Reassessment
Eligibility
Decision
(
TRED)
(
S.
Levy,
22­
AUG­
2002;
DP#
283808).

Adequate
confined
and
field
rotational
crop
studies
are
available
to
support
the
proposed
uses.
Based
on
the
results
of
these
rotational
crop
studies,
HED
concludes
that
the
current
rotational
crop
plant­
back
interval
is
acceptable
and
that
tolerances
for
rotated
crops
are
not
necessary.

Regulatory
Recommendations
and
Residue
Chemistry
Deficiencies
Provided
revised
Sections
B
and
F
are
submitted,
HED
concludes
there
are
no
residue
chemistry
data
requirements
that
would
preclude
establishing
permanent
tolerances
for
residues
of
bifenthrin
per
se
at
0.05
ppm
in/
on
tuberous
and
corm
vegetables
(
subgroup
1C),
3.5
ppm
in/
on
leafy
Brassica
greens
(
subgroup
5B),
0.15
ppm
in/
on
dried
shelled
pea
and
beans,
except
soybean
(
subgroup
6C),
5.0
ppm
in/
on
coriander
leaves
and
seeds,
and
25
ppm
in/
on
coriander
dried
leaves.
Revised
Section
Fs
should
be
submitted
with
the
correct
tolerance
level
and
commodity
definitions,
where
appropriate
(
see
Table
6).
Also,
the
use
directions
for
dried
beans
and
peas
should
be
amended
to
specify
a
minimum
RTI
of
7
days
The
available
field
trial
data
will
also
support
the
use
of
bifenthrin
(
EC)
on
tobacco,
for
which
tolerances
are
not
required.
As
residues
were
<
0.1
ppm
in/
on
all
samples
of
green
tobacco
from
the
field
trials,
no
additional
residue
data
are
required
on
tobacco.
However,
FMC
should
amend
its
use
directions
for
tobacco
to
specify
the
maximum
number
of
foliar
applications
allowed
and
the
maximum
seasonal
use
rate.
The
available
tobacco
field
trials
will
support
use
of
the
2
lb/
gal
Summary
of
Analytical
Chemistr
y
and
Residue
Data
Bi
fenthrin
DP#
s
:
310089,
310874,
313738,
313817,
313299,
and
317208
Page
4
of
21
EC
as
either
a
broadcast
pre­
plant
soil
application
at
up
to
0.1
lb
ai/
A
or
an
in­
furrow
water
drench
application
at
transplant
at
up
to
0.1
lb
ai/
A,
followed
by
a
single
broadcast
foliar
application
up
to
lay­
by
at
up
to
0.1
lb
ai/
A,
for
a
maximum
seasonal
use
rate
of
0.2
lb
ai/
A.
A
revised
Section
B
should
be
submitted.

A
human­
health
risk
assessment
for
bifenthrin
will
be
prepared
in
a
separate
document.

Background
Bifenthrin
is
a
synthetic
pyrethroid
insecticide
(
MOA
Group
3)
that
is
registered
to
FMC
Corporation
for
control
of
insects
on
a
variety
of
fruit,
vegetable,
and
field
crops.
Tolerances
are
established
for
residues
of
bifenthrin
per
se
in/
on
plant
and
livestock
commodities
at
levels
from
0.05
ppm
(
LOQ)
on
various
commodities
to
10.0
ppm
on
dried
hop
cones
[
40
CFR
180.442(
a)].

The
IR­
4
has
submitted
a
series
of
petitions
(
2E6451,
2E6423,
3E6882
and
4E6843)
proposing
the
use
of
bifenthrin,
formulated
as
a
2
lb/
gal
EC
or
a
1.15%
G,
on
tuberous
and
corm
vegetables,
Brassica
leafy
greens,
dried
and
shelled
peas
and
beans
(
except
soybeans),
and
cilantro.
In
conjunction
with
these
uses,
the
petitioner
is
proposing
the
following
tolerances:

Vegetable,
tuberous
and
corm,
subgroup
1C
...........................................................
0.1
ppm
Brassica,
leafy
greens,
subgroup
5B
.......................................................................
3.0
ppm
Pea
and
bean,
dried
shelled,
except
soybean,
subgroup
6C......................................
0.1
ppm
Cilantro,
leaves
.......................................................................................................
5.0
ppm
Cilantro,
dried
leaves
............................................................................................
30.0
ppm
Coriander,
seed
.......................................................................................................
5.0
ppm
In
addition,
FMC
has
proposed
amending
the
2
lb/
gal
EC
formulation
to
include
uses
on
tobacco
(
non­
food/
feed).
The
nomenclature
and
physicochemical
properties
of
bifenthrin
are
presented
below
in
Tables
1
and
2.
Summary
of
Analytical
Chemistr
y
and
Residue
Data
Bi
fenthrin
DP#
s
:
310089,
310874,
313738,
313817,
313299,
and
317208
Page
5
of
21
Table
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
®

Molecular
weight
422.88
IUPAC
name
2­
methylbiphenyl­
3­
ylmethyl(
Z)­(
1RS,
3RS)­
3­(
2­
chloro­
3,3,3­
trifluoroprop­
1­
enyl)­
2,2­
dimethylcyclopropanecarboxylate
or
2­
methylbiphenyl­
3­
ylmethyl(
Z)­(
1RS)­
cis­
3­(
2­
chloro­
3,3,3­
trifluoroprop­
1­
enyl)­
2,2­
dimethylcyclopropanecarboxylate
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
and
1.5%
G
Table
2.
Physicochemical
Properties
of
the
Technical
Grade
Bifenthrin
Parameter
Value
Reference
Melting
range
68­
70.6
º
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
TRED
NA
=
Not
available
860.1200
Directions
for
use
There
are
currently
four
bifenthrin
end­
use
products
(
EPs)
registered
to
FMC
for
use
on
food/
feed
crops.
One
is
a
2
lb/
gal
EC
formulation
marketed
under
the
trade
name
Capture
®
2EC
Insecticide/
Miticide
(
EPA
Reg.
No.
279­
3069)
and
another
is
a
1.15%
G
formulation
marketed
under
the
trade
name
Capture
®
1.15G
Insecticide
(
EPA
Reg.
No.
279­
3244).
IR­
4
is
supporting
the
use
of
the
2
lb/
gal
EC
on
tuberous
and
corm
vegetables
(
subgroup
1C),
Brassica
leafy
greens
(
subgroup
5B),
dried
peas
and
beans
(
subgroup
6C),
cilantro,
and
the
use
of
the
1.15%
G
on
tuberous
and
corm
vegetables.
FMC
is
also
proposing
amending
the
label
for
the
2
lb/
gal
EC
to
Summary
of
Analytical
Chemistr
y
and
Residue
Data
Bi
fenthrin
DP#
s
:
310089,
310874,
313738,
313817,
313299,
and
317208
Page
6
of
21
include
a
non­
food/
feed
use
on
tobacco.
Example
labels
were
provided
and
the
proposed
use
directions
are
summarized
below
in
Table
3.

Table
3.
Summary
of
Proposed
Use
Directions
for
Bifenthrin.

Application
Timing,
Type
and
Equipment
Formulation
[
EPA
reg.
No.]
Single
rate
(
lb
ai/
A)
Max
Number
Applications
per
Season
Max.
Seasonal
Application
Rate
(
lb
ai/
A)
PHI
(
Days)
Use
Directions
and
Limitations
1
Tuberous
and
Corm
Vegetables
(
Crop
subgroup
1C)
1.15%
G
[
279­
3244
]
0.3
In­
furrow
application
at
planting
Ground
equipment
2
lb/
gal
EC
[
279­
3069]
0.3
1
Directed
foliar
applications
during
tuber
formation
Ground
equipment
2
lb/
gal
EC
[
279­
3069]
0.1
2
0.5
21
The
minimum
RTI
is
21
days.

Brassica
leafy
Greens
(
subgroup)
Post­
emergence
broadcast
foliar
applications
Ground
or
aerial
equipment
2
lb/
gal
EC
[
279­
3069]
0.1
4
0.4
7
The
minimum
RTI
is
7
days
Dried
Beans
(
subgroup
6C)
Post­
emergence
broadcast
foliar
applications
Ground
or
aerial
equipment
2
lb/
gal
EC
[
279­
3069]
0.1
3
0.3
14
No
minimum
RTI
is
specified
Dried
Peas
(
subgroup
6C)
Post­
emergence
broadcast
foliar
applications
Ground
or
aerial
equipment
2
lb/
gal
EC
[
279­
3069]
0.1
2
0.2
14
A
minimum
RTI
is
not
specified
Cilantro
(
Coriander)
Post­
emergence
broadcast
foliar
applications
Ground
or
aerial
equipment
2
lb/
gal
EC
[
279­
3069]
0.1
5
0.5
3
The
minimum
RTI
is
7
days.

Tobacco
Pre­
transplant
soil
application
Ground
equipment
0.1
1
NS
At
transplant
water
drench
application
Ground
equipment
0.1
1
NS
Broadcast
foliar
applications
up
to
and
including
lay­
by
Ground
equipment
2
lb/
gal
EC
[
279­
3069]

0.05
NS
NS
NS
Apply
pretransplant
soil
application
and
broadcast
foliar
applications
in
a
minimum
of
10
gal/
A,
and
water
drench
application
in
50­
200
gal/
A
1
Crops
with
bifenthrin
tolerances
may
be
rotated
at
any
time,
and
all
other
corps
may
be
rotated
30
days
following
the
final
bifenthrin
application.
NS
=
not
specified.

Conclusions.
The
proposed
use
directions
for
tuberous
and
corm
vegetables,
leafy
Brassica
greens,
dried
peas
and
beans,
and
cilantro
are
adequately
supported
by
the
available
field
trials
on
potatoes,
mustard
greens,
dried
beans
and
peas,
and
cilantro;
however,
the
use
directions
for
dried
beans
and
peas
should
be
amended
to
specify
a
minimum
RTI
of
7
days.
The
available
tobacco
field
trials
will
also
support
the
use
of
the
EC
formulation
on
tobacco;
however,
the
use
directions
should
be
amended
to
specify
the
maximum
number
of
foliar
applications
allowed
and
the
maximum
seasonal
use
rate.
The
available
tobacco
field
trails
will
support
use
of
the
2
lb/
gal
EC
Summary
of
Analytical
Chemistr
y
and
Residue
Data
Bi
fenthrin
DP#
s
:
310089,
310874,
313738,
313817,
313299,
and
317208
Page
7
of
21
as
either
a
broadcast
pre­
plant
soil
application
at
up
to
0.1
lb
ai/
A
or
an
in­
furrow
water
drench
application
at
transplant
at
up
to
0.1
lb
ai/
A,
followed
by
a
single
broadcast
foliar
application
up
to
lay­
by
at
up
to
0.1
lb
ai/
A,
for
a
maximum
seasonal
use
rate
of
0.2
lb
ai/
A.
These
data
will
also
support
the
use
of
the
1.15%
G
formulation
to
tobacco
as
a
single
broadcast
pre­
plant
soil
application
at
up
to
0.1
lb
ai/
A.
A
revised
Section
B
should
be
submitted.

860.1300
Nature
of
the
Residue
 
Plants.

Bifenthrin
TRED,
S.
Levy,
21­
AUG­
2002;
DP#
283808
45794202.
der
The
nature
of
bifenthrin
residues
in
plants
is
adequately
understood
based
on
the
available
metabolism
studies
on
corn,
cotton,
and
apple.
HED
previously
determined
that
for
purposes
of
tolerance
expression
and
risk
assessment,
the
residue
of
concern
in
cotton
and
apple
commodities
is
bifenthrin
per
se
(
Memos,
M.
Flood,
24­
DEC­
1987
and
N.
Dodd,
02­
JUL­
1987).
After
reexamining
the
cotton
and
apple
metabolism
data
and
additional
corn
metabolism
data,
the
HED
Metabolism
Committee
(
Memo,
M.
Flood,
23­
JUL­
1993)
reaffirmed
that
the
residue
of
concern
in
plant
commodities
is
bifenthrin
per
se.

In
conjunction
with
the
petition
for
use
on
tuberous
and
corm
vegetables,
IR­
4
has
submitted
an
additional
metabolism
study
on
potatoes
reflecting
both
soil
and
foliar
applications
of
[
14C]
bifenthrin.
The
potato
study
is
adequate
and
the
results
from
the
metabolism
study
(
discussed
below)
support
HED's
previous
determination
that
the
residue
of
concern
is
bifenthrin
per
se.

Potato
metabolism.
The
metabolism
of
bifenthrin
in
potatoes
was
examined
in
two
trials
using
either
[
cyclopropyl­
1­
14C]­
or
[
U­
phenyl­
14C]­
labeled
bifenthrin
(
14C­
CP
or
14C­
PH).
Each
14Clabel
was
formulated
as
an
EC
and
applied
to
potatoes
as
a
single
in­
furrow
application
at
0.3
lb
ai/
A,
followed
by
two
broadcast
foliar
applications
at
0.1
lb
ai/
A/
application,
for
a
total
of
0.5
lb
ai/
A
(
1x
rate).
The
foliar
applications
were
made
late
in
the
season
during
the
vegetative
stage,
at
a
RTI
of
14
days.
Samples
of
potato
tubers
and
foliage
were
collected
at
2­
and
14­
day
PHIs.

The
levels
of
radioactivity
in
foliage
and
tubers
were
similar
for
the
[
14C­
CP]
and
[
14C­
PH]
labeled
samples.
Total
radioactive
residues
(
TRR)
in
foliage
were
2.89­
3.29
ppm
at
a
2­
day
PHI
and
declined
to
1.94­
2.70
ppm
by
the
14­
day
PHI.
TRR
were
substantially
lower
in
tubers
(
0.020­
0.068
ppm)
at
both
sampling
intervals,
indicating
that
translocation
of
[
14C]
bifenthrin
from
leaves
to
the
tubers
was
minimal.

Mature
(
14­
day
PHI)
samples
of
tubers
and
foliage
were
extracted
with
acetonitrile
(
ACN),
releasing
91­
96%
of
the
TRR
from
each
matrix.
Solubilized
residues
were
subsequently
partitioned
into
hexane,
ether/
ACN,
and
aqueous
fractions.
Radioactivity
remaining
in
the
residual
solids
accounted
for
7.5­
8.6%
TRR
in
tubers
and
4.3%
of
the
TRR
in
foliage.
With
the
exception
of
several
minor
metabolites,
the
14C­
residue
profiles
in
tubers
and
foliage
were
similar
for
the
two
14C­
labels,
with
identified
residues
accounting
for
75­
81%
of
the
TRR
in
tubers
and
95%
of
the
TRR
in
foliage.
In
all
matrices,
bifenthrin
was
the
major
14C­
residue
accounting
for
73­
81
%
of
the
TRR
in
tubers
and
95%
of
the
TRR
in
foliage.
Minor
amounts
( 
1.2%
TRR,
<
0.001
ppm)
of
the
following
metabolites
were
also
tentatively
identified
by
high­
performance
liquid
chromatography
(
HPLC)
in
tubers:
4­
OH­
bifenthrin,
biphenyl
alcohol
or
acid
metabolites,
a
Summary
of
Analytical
Chemistr
y
and
Residue
Data
Bi
fenthrin
DP#
s
:
310089,
310874,
313738,
313817,
313299,
and
317208
Page
8
of
21
biphenyl
aldehyde
metabolite,
and
TFP
acid
(
see
attachment
2
for
structures).
No
metabolites
were
detected
in
foliage.
Considering
the
type
of
metabolites
detected,
the
metabolism
of
bifenthrin
in
potatoes
appears
to
involve
hydrolytic
cleavage
of
the
ester
linkage
and
hydroxylation
of
the
biphenyl
moiety.

860.1300
Nature
of
the
Residue
 
Livestock.

Bifenthrin
TRED,
S.
Levy,
21­
AUG­
2002;
DP#
283808
Adequate
ruminant
and
poultry
metabolism
studies
are
available
depicting
the
metabolism
of
bifenthrin
radiolabeled
in
either
the
phenyl
or
cyclopropyl
ring.
Based
on
these
data,
the
HED
Metabolism
Committee
(
M.
Flood,
8/
2/
93)
concluded
that
the
residue
of
concern
in
livestock
commodities
is
bifenthrin
per
se.

860.1340
Residue
Analytical
Methods
­
Plants.

Adequate
GC/
ECD
methods
are
available
for
enforcing
bifenthrin
tolerances
on
cottonseed
(
FMC
Method
RAN­
0140),
corn
commodities
(
FMC
Method
P­
2550),
pears
(
FMC
Method
P­
0757),
and
pecans
(
FMC
Method
PC­
0130);
these
methods
have
undergone
successful
petition
method
validation
(
PMV)
trials.
The
general
procedures
of
these
methods
involve
extraction
of
the
sample
with
acetone,
partitioning
with
hexane,
purification
of
the
extract
by
Florisil
column
chromatography,
and
analysis
of
the
extract
by
GC/
ECD.
The
LOQ
for
these
methods
is
0.05
ppm.

Residues
of
bifenthrin
in
samples
from
the
current
crop
field
trials
and
processing
study
were
determined
using
modifications
of
FMC
method
P­
2550
M,
with
variations
in
extraction
solvents
and
detection
methods.
Residues
of
bifenthrin
in/
on
mustard
greens
and
cilantro
(
fresh,
dried,
seeds)
were
determined
using
a
GC/
ECD
method
(
FMC
Report
P­
2132).
For
this
method,
residues
are
extracted
with
hexane,
concentrated,
and
cleaned
up
using
a
Florisil
column,
then
analyzed
by
GC/
ECD.
Residues
in/
on
potato
fractions
and
dried
beans
and
peas
were
determined
using
a
GC/
MSD
method
(
FMC
Report
P­
3426).
For
this
method,
residues
are
extracted
with
acetone,
concentrated,
and
purified
by
silica­
gel
SPE.
The
residues
are
then
analyzed
by
GC/
MSD,
using
the
m/
z
181
ion
for
quantitation.
Residues
in/
on
green
tobacco
were
determined
using
a
related
GC/
MSD
method
(
FMC
Report
P­
3457).
For
this
method,
residues
are
extracted
with
acetone/
water,
partitioned
into
hexane,
and
cleaned
up
with
a
SPE
column,
and
analyzed
by
GC/
MSD.
For
each
of
the
above
methods,
the
LOQ
for
bifenthrin
is
0.05
ppm,
and
the
reported
LOD
is
0.01
ppm.

Each
of
the
above
methods
was
validated
in
conjunction
with
the
field
trials
or
processing
study.
For
potatoes
matrices
fortified
at
0.05­
0.2
ppm,
average
recoveries
were
72­
100%
with
standard
deviations
of
±
7­
12%;
for
mustard
greens
fortified
at
0.05­
6.1
ppm,
average
recoveries
were
73­
104%,
with
standard
deviations
of
±
2­
15%;
for
fresh
cilantro
and
seed
fortified
at
0.05­
4.9
ppm
and
dried
cilantro
fortified
at
0.1­
20
ppm,
average
recoveries
were
79­
92%,
with
standard
deviations
of
±
4­
15%;
and
for
tobacco
fortified
at
0.05
ppm,
the
average
recovery
was
110
±
4%.
Summary
of
Analytical
Chemistr
y
and
Residue
Data
Bi
fenthrin
DP#
s
:
310089,
310874,
313738,
313817,
313299,
and
317208
Page
9
of
21
Conclusion.
The
available
GC/
ECD
or
GC/
MSD
methods
are
adequate
for
collecting
data
on
bifenthrin
residues
in/
on
mustards
greens,
dried
beans
and
peas,
potato
matrices
(
tubers,
chips,
wet
peel,
and
flakes),
cilantro
leaves
(
fresh
and
dried)
and
seeds,
and
green
tobacco.

860.1340
Residue
Analytical
Methods
­
Livestock.

Several
GC/
ECD
methods
are
available
for
enforcing
of
tolerances
for
bifenthrin
in
cattle
tissues
and
milk
(
P­
1031)
and
in
poultry
tissues
(
P­
1843M)
and
eggs
(
RAN­
0204M).
The
general
procedures
of
these
methods
involve
extraction
of
the
sample
with
acetone,
purification
of
the
residues
by
Florisil
column
chromatography,
and
analysis
of
the
residues
by
GC/
ECD.
The
LOQ
for
bifenthrin
is
0.005
ppm
in
eggs,
and
0.05
ppm
in
milk
and
tissues.

860.1360
Multiresidue
Methods
(
MRM)

The
Food
and
Drug
Administration
(
FDA)
PESTDATA
database
dated
10/
99
(
PAM
Vol.
I,
Appendix
II)
indicates
that
bifenthrin
is
completely
recovered
using
MRM
Section
303
and
that
recoveries
using
Section
302
are
variable.
No
information
pertaining
to
the
recovery
of
bifenthrin
using
Section
304
is
available.

860.1380
Storage
Stability.

Bifenthrin
TRED,
S.
Levy,
21­
AUG­
2002;
DP#
283808
Adequate
data
are
available
indicating
that
bifenthrin
is
stable
during
frozen
storage
( ­
18
°
C)
in
a
variety
of
plant
matrices.
Residues
of
bifenthrin
are
stable
during
frozen
storage
for
up
to:
12
months
in
corn
flour,
meal,
oil,
and
starch;
18
months
in/
on
oranges
(
whole)
and
orange
dried
pulp,
juice,
and
oil;
24
months
in/
on
cottonseed;
34
months
in/
on
corn
grain;
36
months
in/
on
lettuce,
pecans,
and
potatoes;
and
49
months
in/
on
apple,
corn
silage,
and
corn
stover.

In
the
current
field
trials
and
potato
processing
study,
the
maximum
frozen
storage
intervals
were
2
months
for
mustard
greens,
dried
peas
and
beans,
and
whole
potatoes,
 
1
month
for
processed
potato
fractions,
8
months
for
green
tobacco,
22
and
23
months
for
cilantro
leaves,
fresh
and
dried,
respectively,
and
17
months
for
seeds.

Conclusion.
The
available
storage
stability
data
are
adequate
to
support
the
sample
storage
intervals
and
conditions
from
the
current
field
trials
and
potato
processing
study.

860.1480
Meat,
Milk,
Poultry,
and
Eggs
Bifenthrin
TRED,
S.
Levy,
21­
AUG­
2002;
DP#
283808
The
maximum
theoretical
dietary
burdens
(
MTDB)
of
bifenthrin
for
livestock
were
recently
calculated
in
the
Bifenthrin
TRED.
Based
on
established
and
recommended
tolerances,
the
MTDB
was
calculated
to
be
2.7
ppm
for
beef
cattle,
3.3
ppm
for
dairy
cattle,
0.14
ppm
for
poultry,
and
Summary
of
Analytical
Chemistr
y
and
Residue
Data
Bi
fenthrin
DP#
s
:
310089,
310874,
313738,
313817,
313299,
and
317208
Page
10
of
21
0.12
ppm
for
hogs.
In
the
current
series
of
petitions,
the
only
crop
with
any
regulated
livestock
feedstuffs
is
potato
(
processed
potato
waste
and
culls).
As
potato
waste
and
culls
are
not
fed
to
poultry,
the
proposed
uses
will
not
have
any
impact
on
the
current
tolerances
for
poultry
commodities.

Using
a
HED­
recommended
tolerance
of
0.05
ppm
for
potato
(
tuber
and
corm
vegetable),
the
MTDB
was
recalculated
for
cattle
and
hogs
(
Table
4).
The
inclusion
of
potato
feedstuffs
did
not
increase
the
MTDB
of
beef
cattle
(
2.73
ppm),
dairy
cattle
(
3.33
ppm),
or
hogs
(
0.12
ppm).
Therefore,
the
proposed
uses
will
not
have
any
impact
on
the
current
milk
or
livestock
tolerances.

Table
4.
Calculation
of
Maximum
Dietary
Burdens
of
Livestock
for
bifenthrin
Residues.

Feed
Commodity
%
Dry
Matter1
%
Diet1
Current
or
Recommended
Tolerance
(
ppm)
Dietary
Contribution
(
ppm)
2
Beef
Cattle
Corn,
sweet,
forage
48
40
3.0
2.5
Potato,
culls
20
35
0.05
0.09
Cotton,
seed
88
25
0.5
0.14
TOTAL
BURDEN
100
2.73
Dairy
Cattle
Corn,
sweet,
forage
48
50
3.0
3.13
Potato,
culls
20
25
0.05
0.06
Cotton,
seed
88
25
0.5
0.14
TOTAL
BURDEN
3.33
Hog
Field
corn,
Grain
88
45
0.05
0.023
Cottonseed,
Meal
89
15
0.5
0.075
Potato,
culls
20
40
0.05
0.02
TOTAL
BURDEN
100
­­
0.12
1
Table
1
(
August
1996).
2
Contribution
=
[
tolerance
÷
%
DM
(
if
cattle)]
×
%
diet.

860.1500
Crop
Field
Trials
45794203.
der1
(
potato)
45660301.
der
(
mustard
greens)
45642701/
der
(
beans
and
peas)
46279701.
der
(
cilantro)
46045001.
der
(
tobacco)

IR­
4
has
submitted
crop
field
trials
supporting
the
use
of
bifenthrin
on
tuberous
and
corm
vegetables
(
subgroup
1C),
leafy
Brassica
vegetables
(
subgroup
5B),
dried
shelled
beans
and
peas
(
subgroup
6C),
and
cilantro.
FMC
has
also
submitted
data
supporting
the
use
of
bifenthrin
on
tobacco.
The
results
from
these
studies
are
discussed
below
and
summarized
in
Table
5.
Summary
of
Analytical
Chemistr
y
and
Residue
Data
Bi
fenthrin
DP#
s
:
310089,
310874,
313738,
313817,
313299,
and
317208
Page
11
of
21
Table
5.
Summary
of
Residue
Data
from
Field
Trials
with
Bifenthrin
(
EC
or
G).
Residue
Levels
(
ppm)
1
Commodity
Form.
Total
Applic.
Rate
(
lb
ai/
A)
PHI
(
days)
n
Min.
Max.
HAFT2
Median
Mean
Std.
Dev.

Potatoes
G
+
EC
0.5
21
24
<
0.05
<
0.05
0.05
0.025
0.025
0
Potatoes3
EC
+
EC
0.5
21
24
<
0.05
<
0.05
0.05
0.025
0.025
0
Mustard
Greens
Mustard
Greens
EC
0.397­
0.427
6­
7
16
<
0.05
2.05
2.01
1.04
1.08
0.71
Dried
Beans
and
Peas
Dried
Beans
EC
0.3
13­
15
18
<
0.05
0.10
0.095
0.025
0.043
0.029
Dried
Peas
EC
0.2
14­
15
12
<
0.05
<
0.05
0.05
0.025
0.025
0
Cilantro
(
Coriander)
Fresh
leaves
EC
0.497­
0.508
3
6
1.98
4.83
3.96
2.73
2.97
0.99
Dried
leaves
EC
0.497
2
2
14.93
16.25
NA
15.60
15.59
0.94
Seeds
EC
0.518
3
2
3.66
3.69
NA
3.67
3.67
0.03
Tobacco
EC
or
G
0.1
85­
176
14
<
0.05
<
0.05
NA
0.025
0.025
NA
EC
0.1
85­
176
14
<
0.05
<
0.05
NA
0.025
0.025
NA
EC
0.15
55­
106
14
<
0.05
<
0.05
NA
0.025
0.025
NA
Green
Tobacco4
EC
0.20­
0.30
55­
106
14
<
0.05
<
0.05
NA
0.025
0.025
NA
1
The
LOQ
is
0.05
ppm
for
all
commodities,
and
the
LOD
is
0.01
ppm.
For
calculation
of
the
median,
mean,
and
standard
deviation,
½
LOQ
was
used
for
samples
with
residues
<
LOQ.
2
HAFT
=
Highest­
Average
Field
Trial.
3
The
use
rate
for
potatoes
reflects
the
use
of
either
an
EC
or
G
formulation
applied
in­
furrow
at
0.3
lb
ai/
A
in
side­
by­
side
trials,
followed
by
two
foliar
applications
of
an
EC
at
0.1
lb
ai/
A/
application.
4
Four
application
regimes
were
used
on
tobacco:
(
1)
a
single
pre­
transplant,
broadcast
application
(
EC
or
G)
at
0.1
lb
ai/
A;
(
2)
a
single
in­
furrow
or
soil
drench
application
(
EC)
at
transplanting
at
0.1
lb
ai/
A;
an
in­
furrow
or
soil
drench
application
(
EC)
at
0.1
lb
ai/
A
at
transplanting,
followed
by
a
single
broadcast
foliar
application
(
EC)
at
0.05
lb
ai/
A,
for
a
total
of
0.15
lb
ai/
A/
season
;
and
(
4)
an
in­
furrow
or
soil
drench
application
(
EC)
at
0.1
or
0.2
lb
ai/
A
at
transplanting,
followed
by
a
single
broadcast
foliar
application
(
EC)
at
0.1
lb
ai/
A,
for
a
total
of
0.2
or
0.3
lb
ai/
A/
season
.

Potatoes:
Twelve
potato
field
trials
were
conducted
during
2001
comparing
the
use
of
two
bifenthrin
formulations.
At
each
trial,
bifenthrin
(
2
lb/
gal
EC
or
1.15%
G)
was
applied
to
potatoes
as
one
in­
furrow
application
at
0.3
lb
ai/
A
followed
by
two
broadcast
foliar
applications
of
the
2
lb/
gal
EC
at
0.1
lb
ai/
A/
application,
for
a
total
of
0.5
lb
ai/
A/
season
(
1x
proposed
rate).
The
infurrow
application
was
made
prior
to
planting,
and
the
foliar
applications
were
made
late
in
the
season,
approximately
42
and
21
days
prior
to
normal
maturity.
Duplicate
control
and
treated
samples
of
potatoes
were
harvested
at
commercial
maturity
from
treatment
at
each
trial
site,
at
approximately
20­
21­
day
PHIs.
Samples
were
stored
frozen
for
up
to
1
month,
an
interval
supported
by
the
available
storage
stability
data.

The
GC­
MSD
method
(
FMC
Report
P­
3426)
used
to
determine
bifenthrin
residues
in/
on
potatoes
was
adequately
validated
in
conjunction
with
the
field
trial
analyses.
The
validated
LOQ
was
0.05
ppm,
and
the
LOD
was
0.01
ppm.

Regardless
of
the
type
of
formulation
used
for
the
in­
furrow
application
(
G
or
EC),
bifenthrin
residues
were
<
LOQ
(<
0.05
ppm)
in/
on
all
48
samples
of
potatoes
harvested
~
20­
21
DAT
following
applications
at
1x.
The
average
and
HAFT
residues
in/
on
potatoes
were
0.025
and
0.05
ppm,
respectively.
Residue
decline
information
could
not
be
determined
from
the
two
decline
trials
because
of
the
lack
of
residues
found
at
any
of
the
sampling
points.
Summary
of
Analytical
Chemistr
y
and
Residue
Data
Bi
fenthrin
DP#
s
:
310089,
310874,
313738,
313817,
313299,
and
317208
Page
12
of
21
Mustard
Greens:
In
eight
field
trials
conducted
during
1999,
bifenthrin
(
2
lb/
gal
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
(
1x
the
propose
rate).
Applications
were
made
during
vegetative
growth,
at
RTIs
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
PHIs.
Samples
were
stored
frozen
for
up
to
2
months
prior
to
analysis,
an
interval
supported
by
the
available
storage
stability
data.

The
GC/
ECD
method
(
FMC
Report
P­
2132M,
modified)
used
to
determine
bifenthrin
residues
in/
on
mustard
greens
was
adequately
validated
in
conjunction
with
the
field
trial
analyses.
The
validated
LOQ
was
0.05
ppm.
The
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,
following
applications
at
1x
the
proposed
rate.
The
average
and
HAFT
residues
in/
on
mustard
greens
were
1.04
and
2.01
ppm,
respectively.
Residue
decline
data
were
not
provided.

Dried
Beans
and
Peas:
A
total
of
15
field
trials
were
conducted
during
2001
on
dried
beans
(
9
trials)
and
peas
(
6
trials),
which
are
the
representative
crops
for
Crop
subgroup
6C.
Bifenthrin
(
2
lb/
gal
EC)
was
applied
to
dried
beans
as
three
broadcast
foliar
applications
at
0.1
lb
ai/
A/
application,
for
a
total
of
0.3
lb
ai/
A/
season
(
1x
proposed
rate).
The
initial
application
was
made
at
the
2­
6
node
stage,
the
second
application
was
made
at
bloom
through
pod
fill,
and
the
final
application
was
made
at
early
maturity,
~
14
days
prior
to
normal
harvest.
The
RTIs
for
dried
beans
were
10­
44
days.
In
the
six
dried
pea
field
trials,
bifenthrin
(
2
lb
/
gal
EC)
was
applied
as
two
broadcast
foliar
applications
at
0.1
lb
ai/
A/
application,
at
approximately
21
and
14
days
prior
to
normal
maturity,
for
a
total
of
0.2
lb
ai/
A/
season
(
1x
the
proposed
rate).
The
RTIs
for
the
dried
pea
trials
were
6­
7
days.
At
commercial
maturity
(
13­
15
day
PHIs),
a
single
control
and
duplicate
treated
samples
of
dried
beans
or
peas
were
collected
from
each
trial.
To
examine
residue
decline,
additional
duplicate
samples
were
collected
at
9,
14,
19,
and
27
day
PHIs
from
one
dried
bean
trial
and
at
12,
15,
20,
and
27
day
PHIs
from
one
dried
pea
trial.
Samples
were
stored
frozen
for
up
to
2
months,
an
interval
supported
by
the
available
storage
stability
data.

The
GC/
MSD
method
(
FMC
Report
P­
3426)
used
to
determine
bifenthrin
residues
in/
on
beans
and
peas
was
adequately
validated
in
conjunction
with
the
field
trial
analyses.
The
validated
LOQ
was
0.05
ppm,
and
the
LOD
was
0.01
pm.

Following
applications
at
1x
the
proposed
rate,
residues
of
bifenthrin
were
<
0.01­
0.10
ppm
in/
on
18
samples
of
dried
beans
harvested
13­
15
DAT,
and
<
LOQ
in/
on
all
12
samples
of
dried
peas
(<
0.01­
0.02
ppm)
harvested
at
14­
15
DAT.
The
average
residues
were
0.043
ppm
for
dried
beans
and
0.025
ppm
for
dried
peas.
Residue
decline
could
not
be
determined
for
dried
beans,
as
residues
in
all
samples
from
the
decline
trial
were
<
LOD.
However,
residues
in
dried
peas,
although
low
( 
0.02
ppm),
did
show
decline
at
longer
post­
treatment
intervals.

Cilantro
(
Coriander):
In
four
field
trials
conducted
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
(
1x
proposed
rate).
Applications
were
made
beginning
at
the
1­
4
true­
leaf
stage,
at
RTIs
of
6­
7
days.
At
commercial
maturity,
samples
of
fresh
cilantro
foliage
(
3
trials)
and
seeds
(
1
trial)
were
harvested
3
DAT.
At
one
of
the
trial
sites,
additional
samples
of
fresh
cilantro
were
harvested
at
2
DAT
and
dried
in
ovens
for
2
days
to
yield
dried
cilantro
Summary
of
Analytical
Chemistr
y
and
Residue
Data
Bi
fenthrin
DP#
s
:
310089,
310874,
313738,
313817,
313299,
and
317208
Page
13
of
21
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
stability
data.

The
GC/
ECD
method
used
to
determine
bifenthrin
residues
in/
on
cilantro
(
FMC
Report
P­
2132M,
modified)
was
adequately
validated
in
conjunction
with
the
field
trial
analyses.
The
validated
LOQ
was
0.05
ppm.

Following
applications
at
1x
rate,
bifenthrin
residues
were
1.98­
4.83
ppm
in/
on
6
samples
of
fresh
cilantro
foliage
harvested
3
DAT,
14.93­
16.25
ppm
in/
on
2
dried
cilantro
samples
harvested
2
DAT,
and
3.66­
3.69
ppm
in/
on
2
cilantro
seed
samples
harvested
3
DAT.
The
average
and
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.

Tobacco
(
non­
food/
feed):
Field
trials
on
tobacco
were
conducted
at
three
trial
sites
in
VA
(
2)
and
GA
(
1)
during
2002,
with
four
different
application
regimes
being
tested
at
each
field
site.
The
four
application
regimes
included:
(
i)
a
single
pre­
transplant,
broadcast
application
of
either
the
2
lb/
gal
EC
or
1.15%
G
formulation
at
0.1
lb
ai/
A
(
Plot
1);
(
ii)
a
single
in­
furrow
or
soil
drench
application
of
the
2
lb/
gal
EC
at
transplanting
at
0.1
lb
ai/
A
(
Plot
2);
a
combination
of
an
in­
furrow
or
soil
drench
application
of
the
2
lb/
gal
EC
at
0.1
lb
ai/
A
at
transplanting,
followed
­

1
month
later
by
a
single
broadcast
foliar
application
of
the
2
lb/
gal
EC
at
0.05
lb
ai/
A,
for
a
total
of
0.15
lb
ai/
A/
season
(
Plot
3);
and
(
iv)
a
combination
of
an
in­
furrow
or
soil
drench
application
of
the
2
lb/
gal
EC
at
0.1
or
0.2
lb
ai/
A
at
transplanting,
followed
­

1
month
later
by
a
single
broadcast
foliar
application
of
the
2
lb/
gal
EC
at
0.1
lb
ai/
A,
for
a
total
of
0.2
or
0.3
lb
ai/
A/
season
(
Plot
4).

For
the
first
VA
field
trial,
tobacco
was
harvested
three
times
between
90­
176
DAT
from
Plots
1
and
2,
and
57­
106
DAT
from
Plots
3
and
4.
For
the
GA
field
trial,
tobacco
was
also
harvested
three
times
between
85­
128
DAT
from
Plots
1
and
2
and
55­
98
DAT
from
Plots
3
and
4.
For
the
second
VA
field
trial,
tobacco
was
harvested
only
once
at
105
or
142
DAT
from
Plots
1
and
2
and
at
72
DAT
from
Plots
3
and
4.
At
each
harvest
interval,
a
single
control
and
duplicate
treated
samples
of
green
tobacco
were
harvested
from
each
trial
plot.

Residues
of
bifenthrin
in/
on
green
tobacco
were
determined
using
a
GC/
MSD
method
(
FMC
Report
P­
3457).
The
method
LOQ
is
0.05
ppm,
and
the
LOD
is
0.01
ppm.
Bifenthrin
residues
were
<
0.05
ppm
(<
LOQ)
in/
on
all
green
tobacco
samples
from
each
application
regime
at
all
harvest
intervals.

Conclusions.
The
field
trials
on
potatoes,
mustard
greens,
dried
beans
and
peas,
cilantro,
and
tobacco
are
adequate.
An
adequate
number
of
trials
were
conducted
reflecting
the
proposed
use
patterns
in
the
appropriate
geographic
regions,
and
the
appropriate
commodities
were
collected
at
the
proposed
PHIs.
Samples
were
analyzed
using
adequate
analytical
methods,
and
the
sample
storage
intervals
are
supported
by
the
available
storage
stability
data.
The
available
potato
data
will
support
a
tolerance
of
0.05
ppm
on
tuberous
and
corm
vegetables
(
subgroup
1C),
and
the
mustard
green
data
will
support
a
tolerance
of
3.5
ppm
on
leafy
Brassica
vegetables
(
subgroup
5B).
The
data
on
dried
beans
and
peas
will
support
a
tolerance
of
0.15
ppm
on
shelled
dried
beans
and
peas,
excluding
soybean
(
subgroup
6C).
The
data
on
cilantro
(
coriander)
will
support
separate
tolerances
of
5
ppm
in/
on
coriander
leaves
and
seed.
Based
on
the
HAFT
residues
observed
for
Summary
of
Analytical
Chemistr
y
and
Residue
Data
Bi
fenthrin
DP#
s
:
310089,
310874,
313738,
313817,
313299,
and
317208
Page
14
of
21
coriander
leaves
(
3.96
ppm)
and
the
observed
processing
factor
of
5.7x
for
dried
leaves,
the
maximum
expected
residues
in/
on
dried
leaves
would
be
22.6
ppm,
which
will
support
at
tolerance
of
25
ppm
for
dried
coriander
leaves.

Provided
that
the
use
directions
on
tobacco
are
clarified
with
regards
to
the
number
of
foliar
applications
allowed
and
the
maximum
seasonal
use
rate,
the
available
field
trial
data
will
support
the
use
of
bifenthrin
on
tobacco.
As
residues
in/
on
all
samples
of
green
tobacco
from
the
tobacco
field
trails
were
<
0.1
ppm,
no
additional
data
are
required
to
support
this
use.

860.1520
Processed
Food
and
Feed
45794203.
der2
(
potato)

In
a
field
trial
conducted
during
2001
in
WA,
bifenthrin
(
1.15%
G
and
2
lb/
gal
EC)
was
applied
to
potatoes
as
a
single
in­
furrow
application
at
0.5
lb
ai/
A,
followed
by
two
broadcast
foliar
applications
at
0.5
lb
ai/
A,
for
a
total
of
1.5
lb
ai/
A/
season
(
3x
rate).
The
foliar
applications
were
made
during
tuber
development
at
42
and
21
days
prior
to
normal
maturity.
Bulk
samples
of
potatoes
were
harvested
at
commercial
maturity,
at
a
21­
day
PHI,
and
processed
into
chips,
granules
and
wet
peel
using
simulated
commercial
practices.
Prior
to
analysis,
potato
tubers
(
raw
agricultural
commodity
(
RAC)),
chips,
granules
and
peels
were
stored
frozen
up
to
1
month,
an
interval
supported
by
the
available
storage
stability
data.

The
GC­
MSD
method
(
FMC
Report
P­
3426)
used
to
determine
bifenthrin
residues
in/
on
potatoes
(
RAC)
and
processed
potato
products
was
adequately
validated
in
conjunction
with
the
sample
analyses.
The
validated
LOQ
was
0.05
ppm
for
bifenthrin
in/
on
potatoes
and
potato
processing
products;
the
LOD
was
0.01
ppm.

Following
applications
totaling
1.5
lb
ai/
A
(
3x
rate),
residues
of
bifenthrin
were
nondetectable
(<
0.01
ppm)
in/
on
potatoes
(
RAC)
harvested
at
a
21­
day
PHI,
and
in
processed
samples
of
chips
and
granules.
Residues
in
wet
peel
were
detectable
at
0.02­
0.04
ppm,
but
were
still
below
the
LOQ.
As
residues
were
<
LOD
in
potatoes,
a
processing
factor
for
potato
chips
and
granules
could
not
be
calculated,
and
the
processing
factor
for
wet
peel
was
estimated
to
be
3x.
The
maximum
theoretical
concentration
factor
for
potatoes
is
5x.

Conclusions.
The
available
potato
processing
study
is
adequate.
Because
bifenthrin
residues
were
<
LOQ
in
all
samples
from
the
potato
field
trials
(
46229403.
der1)
and
in
potatoes
(
RAC)
and
all
processed
fractions
from
the
3x
treatment
level,
HED
concludes
that
residues
of
bifenthrin
in
wet
peel
are
unlikely
to
exceed
the
LOQ
when
bifenthrin
is
applied
at
a
1x
rate.
Therefore,
separate
tolerances
will
be
not
required
for
processed
potato
fractions.

860.1650
Submittal
of
Analytical
Reference
Standards
The
analytical
reference
standard
for
bifenthrin
has
been
submitted
to
the
EPA
National
Pesticide
Standards
Repository.
Summary
of
Analytical
Chemistr
y
and
Residue
Data
Bi
fenthrin
DP#
s
:
310089,
310874,
313738,
313817,
313299,
and
317208
Page
15
of
21
860.1850/
1900
Confined
and
Field
Accumulation
in
Rotational
Crops
Bifenthrin
TRED,
S.
Levy,
21­
AUG­
2002;
DP#
283808
Adequate
confined
and
field
rotational
crop
studies
are
available.
Based
on
the
confined
study,
HED
has
concluded
that
the
residue
of
concern
in
rotational
crops
is
the
parent
compound
only.
Based
on
a
maximum
seasonal
use
rate
of
0.5
lb
ai/
A
for
annual
crops,
the
confined
study
and
the
available
field
rotational
crop
study
on
wheat
also
support
the
current
rotational
crop
restrictions
on
the
labels.
Crops
having
bifenthrin
tolerances
may
be
replanted
at
any
time,
and
all
other
crops
may
be
replanted
30
days
following
the
last
application
of
bifenthrin.
No
rotational
crop
tolerances
are
required.

860.1550
Proposed
Tolerances
HED
has
concluded
that
tolerance
expression
for
plant
and
livestock
commodities
should
include
only
parent
bifenthrin.
Tolerances
for
bifenthrin
residues
are
currently
established
on
plant
commodities
at
levels
ranging
from
0.05
ppm
(
LOQ)
on
various
commodities
to
10.0
ppm
on
dried
hop
cones
[
40
CFR
§
180.568(
a)].
The
tolerances
proposed
by
the
registrants
in
the
current
vegetable
petitions
are
listed
below
in
Table
6,
along
with
HED's
recommended
tolerance
levels.
The
appropriate
tolerance
levels
were
calculated
using
the
methodology
formulated
by
the
NAFTA
MRL/
Tolerance
Harmonization
Workgroup
for
calculating
statistically­
based
pesticide
tolerances
for
plant
commodities
based
on
field
trial
residue
data
(
Attachment
2).
Maximum
likelihood
estimation
(
MLE)
techniques
were
used
to
supplement
the
dried
bean
dataset.
Based
on
visual
inspection
of
the
probability
plot,
the
lognormality
assumption
was
rejected
(
HED
Science
Advisory
Council
for
Chemistry
(
ChemSAC)
meeting
of
3/
8/
06).
The
value
derived
by
the
California
Method
(
0.15
ppm)
was
thus
deemed
to
be
appropriate.
Revised
Sections
F
with
the
correct
tolerance
levels
and
commodity
definitions
should
be
submitted
where
appropriate.

The
available
potato
data
will
support
a
tolerance
of
0.05
ppm
on
tuberous
and
corm
vegetables
(
subgroup
1C),
and
the
mustard
green
data
will
support
a
tolerance
of
3.5
ppm
on
leafy
Brassica
vegetables
(
subgroup
5B).
The
data
on
dried
beans
and
peas
will
support
a
tolerance
of
0.15
ppm
on
shelled
dried
beans
and
peas,
excluding
soybean
(
subgroup
6C).
The
data
on
cilantro
(
coriander)
will
support
separate
tolerances
of
5
ppm
in/
on
coriander
leaves
and
seed.
Based
on
the
HAFT
residues
observed
for
coriander
leaves
(
3.96
ppm)
and
the
observed
processing
factor
of
5.7x
for
dried
leaves,
the
maximum
expected
residues
in/
on
dried
leaves
would
be
22.6
ppm,
which
will
support
at
tolerance
of
25
ppm
for
dried
coriander
leaves.
Summary
of
Analytical
Chemistr
y
and
Residue
Data
Bi
fenthrin
DP#
s
:
310089,
310874,
313738,
313817,
313299,
and
317208
Page
16
of
21
Table
6.
Tolerance
Summary
for
Bifenthrin
Crop
Commodity
Proposed
Tolerance
(
ppm)
Recommended
Tolerance
(
ppm)
Comments
(
correct
commodity
definition)
Tuberous
and
corm
vegetables,
subgroup
1C
0.1
0.05
Vegetable,
tuberous
and
corm,
subgroup
1C
Brassica,
leafy
greens,
subgroup
5B1
3
3.5
Turnip
greens1
3
3.5
Turnip,
greens
Pea
and
bean,
dried
shelled,
except
soybean,
subgroup
0.1
0.15
Pea
and
bean,
dried
shelled,
except
soybean,
subgroup
6C
Cilantro,
leaves
5.0
6.0
Coriander,
leaves
Cilantro,
dried
leaves
30.0
25
Coriander,
dried
leaves
Coriander,
seed
5.0
5.0
1
Turnip
greens
will
be
removed
from
Crop
Group
2:
Leaves
of
root
and
tuber
vegetables
group
[
40
CFR
180.41
(
2)],
and
will
become
a
member
of
Crop
Group
5:
Brassica
leafy
vegetables
[
40
CFR
180.41
(
5)].
It
will
also
be
a
member
of
Crop
Subgroup
5B:
Leafy
Brassica
greens
(
Commodity
Reviewers
Guide,
B.
Schneider,
14­
JUN­
2002).
Until
that
time,
"
turnip,
greens"
should
have
a
separate
tolerance.

International
Tolerances
The
Codex
Alimentarius
Commission
has
established
maximum
residue
limits
(
MRLs)
for
residues
of
bifenthrin
in/
on
various
commodities.
Codex
MRLs
are
expressed
in
terms
of
bifenthrin
per
se,
as
are
U.
S.
tolerances.
The
only
established
Codex
MRL
relevant
to
the
current
petitions
is
for
potato
at
0.05
mg/
kg
(
See
attached
International
Residue
Limits
Status
sheet).
As
the
recommended
tolerance
of
tuberous
and
corm
vegetables
is
also
0.05
ppm,
this
tolerance
is
in
harmony
with
the
Codex
MRL
for
potato.
There
are
no
equivalent
Canadian
or
Mexican
MRLs
for
the
tolerances
being
requested
in
the
current
petition.
Summary
of
Analytical
Chemistr
y
and
Residue
Data
Bi
fenthrin
DP#
s
:
310089,
310874,
313738,
313817,
313299,
and
317208
Page
17
of
21
References
DP
Barcode:
None
Subject:
The
Metabolism
Committee
Meeting
Held
on
July
27,
1993.
Plant
and
Animal
Metabolism
of
Bifenthrin.
From:
M.
Flood
To:
Metabolism
Committee
Dated:
8/
2/
93
MRID(
s):
None
DP
Barcode:
D283808
Subject:
Bifenthrin.
Residue
and
Product
Chemistry
Considerations
for
the
Tolerance
Reassessment
Eligibility
Decision
(
TRED).
From:
S.
Levy
To:
T.
Myers
Dated:
8/
21/
02
MRID:
None
Attachments
Attachment
1.
International
Residue
Limits
Status
sheet
Attachment
2.
Bifenthrin
Metabolites
from
Potato
Metabolism
Study
Attachment
3.
Tolerance
Assessment
Calculations
RDI:
P.
V.
Shah
(
3/
1/
06),
RAB1
Chemists
(
3/
1/
06)
G.
F.
Kramer:
806T:
CM#
2:(
703)
305­
5079:
7509C:
RAB1
Template
Version
September
2003
Summary
of
Analytical
Chemistr
y
and
Residue
Data
Bi
fenthrin
DP#
s
:
310089,
310874,
313738,
313817,
313299,
and
317208
Page
18
of
21
Attachment
1.

INTERNATIONAL
RESIDUE
LIMIT
STATUS
Chemical
Name:
2­
methyl(
1,1'­
biphenyl)­
3­
yl)
methyl(
1R,
3R)­
3­((
1Z)­
2­
chloro­
3,3,3­
trifluoro­
1­
propenyl)­
2,2­
dimethylcyclopropanecarbo
xylate
Common
Name:
Bifenthrin
X
Proposed
tolerance
9
Reevaluated
tolerance
9
Other
Date:
10/
23/
05
Codex
Status
(
Maximum
Residue
Limits)
U.
S.
Tolerances

No
Codex
proposal
step
6
or
above

No
Codex
proposal
step
6
or
above
for
the
crops
requested
Petition#
s:
2E6451,
2E6423,
3E6882
and
4E6843.
DP#
s:
310089,
310874,
313738,
313817,
313818,
and
313299
Other
Identifier:

Reviewer/
Branch:
S.
Levy
Residue
definition
(
step
8/
CXL):
Bifenthrin
Proposed
Residue
definition:
Bifenthrin
Crop
(
s)
MRL
(
mg/
kg)
Crop(
s)
Tolerance
(
ppm)

Potato
0.05
Tuberous
and
corm
vegetables,
subgroup
1C
0.05
Leafy
Brassica
greens,
subgroup
5B
2.5
Dried
shelled
pea
and
bean
(
except
soybean),
subgroup
6C
0.10
Coriander,
leaves
5.0
Coriander,
leaves,
dried
25.0
Coriander,
seed
5.0
Limits
for
Canada
Limits
for
Mexico
9
No
Limits
X
No
Limits
for
the
crops
requested
9
No
Limits
X
No
Limits
for
the
crops
requested
Residue
definition:
NA
Residue
definition:
Bifenthrin
Crop(
s)
MRL
(
mg/
kg)
Crop(
s)
MRL
(
mg/
kg)

Notes/
Special
Instructions:

Rev.
1998
Summary
of
Analytical
Chemistr
y
and
Residue
Data
Bi
fenthrin
DP#
s
:
310089,
310874,
313738,
313817,
313299,
and
317208
Page
19
of
21
Attachment
2.
Bifenthrin
Metabolites
from
Potato
Metabolism
Study
Common
name/
code
Figure
C.
3.1
ID
No.
Chemical
name
Chemical
structure
TFP
Acid
Cis­
3­(
2­
chloro­
3,
3,
3­
trifluoroprop­
1­
enyl)­
2,
2­
dimethylcyclopropanecarboxylic
acid
Cl
O
OH
F
3
C
CH
3
C
H
3
Biphenyl
Aldehyde
2­
methylbiphenyl­
3­
carboxaldehyde
O
C
H
3
Biphenyl
Acid
2­
methylbiphenyl­
3­
carboxylic
acid
OH
O
C
H
3
4'
Hydroxy
bifenthrin
4'­
hydroxy­
2­
methylbiphenyl­
3­
ylmethyl
(
Z)
cis
3­(
2­
chloro­
3,
3,
3­
trifluoroprop­
1­
enyl)­
2,
2­
dimethylcyclopropanecarboxylate
O
O
Cl
F
3
C
OH
CH
3
C
H
3
CH
3
Biphenyl
Alcohol
2­
methylbipheny­
3­
methanol
OH
C
H
3
Summary
of
Analytical
Chemistr
y
and
Residue
Data
Bi
fenthrin
DP#
s
:
310089,
310874,
313738,
313817,
313299,
and
317208
Page
20
of
21
Attachment
3.
Tolerance
Assessment
Calculations
Chemical:
Bifenthrin
Crop:
Mustard
Greens
PHI:
PHI=
7
App.
Rate:
0.397­
0.427
lb
ai/
A/
season
Submitter:

Residues
LN(
Residues)
Zscores
1.850
0.62
0.76
1.710
0.54
0.57
2.050
0.72
1.77
1.970
0.68
1.28
1.390
0.33
0.23
1.170
0.16
0.08
0.750
­
0.29
­
0.57
0.910
­
0.09
­
0.08
0.050
­
3.00
­
1.77
0.080
­
2.53
­
1.28
0.180
­
1.71
­
0.99
0.190
­
1.66
­
0.76
1.900
0.64
0.99
1.450
0.37
0.40
0.850
­
0.16
­
0.23
0.840
­
0.17
­
0.40
Chemical:
Bifenthrin
Crop:
Cilantro
PHI:
PHI=
3
App.
Rate:
0.497­
0.518
lb
ai/
A/
season
Submitter:

Residues
LN(
Residues)
Zscores
1.980
0.68
­
1.43
2.440
0.89
­
0.85
2.840
1.04
­
0.15
2.610
0.96
­
0.47
3.660
1.30
0.47
3.690
1.31
0.85
4.830
1.57
1.43
3.090
1.13
0.15
Summary
of
Analytical
Chemistr
y
and
Residue
Data
Bi
fenthrin
DP#
s
:
310089,
310874,
313738,
313817,
313299,
and
317208
Page
21
of
21
Chemical:
Bifenthrin
Crop:
Dried
Beans
(
MLE)

PHI:
PHI
=
14
App.
Rate:
0.3
Submitter:

Residues
LN(
Residues)
Zscores
0.001170476
­
6.75
­
1.82
0.001982736
­
6.22
­
1.35
0.02
­
3.91
­
0.07
0.03
­
3.51
0.07
0.03
­
3.51
0.21
0.03
­
3.51
0.35
0.002819934
­
5.87
­
1.06
0.003721372
­
5.59
­
0.85
0.004710501
­
5.36
­
0.66
0.005808347
­
5.15
­
0.50
0.1
­
2.30
1.35
0.09
­
2.41
1.06
0.07
­
2.66
0.66
0.1
­
2.30
1.82
0.07
­
2.66
0.85
0.05
­
3.00
0.50
0.007037443
­
4.96
­
0.35
0.00842402
­
4.78
­
0.21
