Bifenazate
(
000586)
Residue
Chemistry
Summary
D324430
page
1
of
16
UNITED
STATES
ENVIRONMENTAL
PROTECTION
AGENCY
WASHINGTON,
D.
C.
20460
OFFICE
OF
PREVENTION,
PESTICIDES,
AND
TOXIC
SUBSTANCES
MEMORANDUM
Date:
19­
July­
2006
Subject:
Bifenazate
(
PC
Code
000586).
Section
3
Registration
for
Application
of
Bifenazate
to
Tuberous
and
Corm
Vegetable
(
crop
subgroup
1c)
and
Succulent
Pea.
Summary
of
Residue
Chemistry
Data.

DP
#:
324430
Registration
#:
5E6992
PC
Code:
000586
Decision
#:
360901
MRID
No.:
46651701,
46651703,
and
46651702
40
CFR:
180.572
From:
Tom
Bloem,
Chemist
Registration
Action
Branch
1/
Health
Effects
Division
(
RAB1/
HED;
7509P)

Through:
George
Kramer,
Ph.
D.,
Branch
Senior
Chemist
RAB1/
HED
(
7509P)

To:
Daniel
Rosenblatt/
Sidney
Jackson
(
RM
05)
Registration
Division
(
7505P)

The
Interregional
Research
Project
Number
4
(
IR­
4)
requested
a
Section
3
registration
for
the
application
of
bifenazate
to
tuberous
and
corm
vegetables
(
crop
subgroup
1c)
and
succulent
pea.
In
conjunction
with
this
request,
the
petitioner
requested
the
establishment
of
the
following
permanent
tolerances
for
the
combined
residues
of
bifenazate
(
hydrazinecarboxylic
acid,
2­(
4­
methoxy­[
1,1'­
biphenyl]­
3­
yl),
1­
methylethyl
ester)
and
D3598
(
diazinecarboxylic
acid,
2­(
4­
methoxy­[
1,1'­
biphenyl]­
3­
yl),
1­
methylethyl
ester)
expressed
as
bifenazate
(
see
attachment
1
for
structures):

pea,
garden............................................................................................................................
0.2
ppm
pea,
edible
podded.................................................................................................................
4.0
ppm
vegetable,
tuberous
and
corm,
subgroup
1c
.........................................................................
0.01
ppm
Bifenazate
(
000586)
Residue
Chemistry
Summary
D324430
page
2
of
16
Executive
Summary
Background:
Bifenazate
is
a
selective
miticide
which
controls
the
motile
stage
of
mites
either
by
direct
contact
or
through
contact
with
foliar
residues.
The
petitioner
indicated
that
bifenazate
blocks
or
closes
the
gamma­
aminobutyric
acid
(
GABA)
activated
chloride
channels
of
susceptible
pests
resulting
in
over­
excitation
of
the
peripheral
nervous
system.
Bifenazate
tolerances
are
currently
established
in/
on
several
crops
and
in
ruminant
commodities
as
a
result
of
secondary
residues
(
40
CFR
180.572).

Application
Scenarios:
The
petitioner
proposed
single
foliar
applications
of
Acramite
®
­
4SC
(
suspension
concentrate;
4
lb
ai/
gal;
EPA
Reg.
No.
­
400­
514)
to
succulent
pea
and
tuberous
and
corm
vegetables
(
crop
subgroup
1c).
The
proposed
label
indicates
that
application
through
irrigation
equipment
is
prohibited
and
does
not
include
rotational
crop
restrictions.
Table
3
is
a
summary
of
the
proposed
application
scenario.

The
submitted
label
adequately
describes
the
proposed
application
scenarios.
Based
on
the
current
rotational
crop
data,
HED
concludes
that
a
30­
day
rotational
crop
restriction
is
appropriate
for
all
nonlabeled
crops
(
labeled
crops
may
be
planted
at
anytime;
see
section
OPPTS
860.1850).
A
revised
Section
B
is
requested.

Nature
of
the
Residue
­
Plants:
Based
on
apple,
orange,
and
cotton
metabolism
studies,
the
HED
Metabolism
Assessment
Review
Committee
(
MARC)
determined
that
for
tolerance
expression
and
risk
assessment
purposes,
the
residues
of
concern
in
these
crops
are
bifenazate
and
D3598
(
D276801,
T.
Bloem,
16­
Aug­
2001).
The
metabolic
route
in
apple,
orange,
and
cotton
were
similar
and
proceeded
via
oxidation
of
the
hydrazine
moiety
of
bifenazate
to
form
D3598
which
is
further
degraded
to
D1989,
D9963,
D4642,
and/
or
A1530
and
to
bound
residues
by
reaction
with
natural
products.

Subsequent
to
this
decision,
the
petitioner
submitted
a
radish
metabolism
study.
The
metabolic
route
in
radish
was
similar
to
that
of
apple,
orange,
and
cotton
with
the
major
identified
residues
being
bifenazate
and
D3598.
HED
concludes
that
the
nature
of
the
residue
in
plants
is
adequately
understood
and
the
residues
of
concern
for
tolerance
expression
and
risk
assessment
purposes
are
bifenazate
and
D3598.

Nature
of
the
Residue
­
Livestock:
The
MARC
reviewed
goat
and
hen
metabolism
studies
and
determined
that
for
tolerance
expression
and
risk
assessment
purposes,
the
residues
of
concern
in
livestock
tissue
(
excluding
fat),
eggs,
and
milk
are
bifenazate,
D3598
(
expressed
as
bifenazate),
A1530,
and
A1530­
sulfate
(
expressed
as
A1530).
The
residues
of
concern
for
tolerance
expression
and
risk
assessment
purposes
in
fat
are
bifenazate
and
D3598
(
expressed
as
bifenazate).
The
metabolic
route
in
goats
and
hens
were
similar
and
proceeded
via
oxidation
of
the
hydrazine
moiety
of
bifenazate
to
form
D3598
which
is
further
degraded
to
D1989,
D9569,
A1530,
and/
or
A1530
­
sulfate
and
to
bound
residues
by
reaction
with
natural
products
(
D276801,
T.
Bloem,
16­
Aug­
2001).

Subsequent
to
this
decision,
the
petitioner
submitted
a
radiovalidation
study
which,
for
purposes
of
sample
generation,
dosed
goats
with
14C­
bifenazate
uniformly
labeled
in
the
o­
methyl
phenyl
ring
for
Bifenazate
(
000586)
Residue
Chemistry
Summary
D324430
page
3
of
16
four
consecutive
days
(
20­
ppm
daily
dietary
burden).
Milk,
liver,
and
fat
samples
were
collected,
extracted
with
a
variety
of
solvents,
and
analyzed
using
the
same
methods
employed
in
the
goat
metabolism
study
(
lactating
goat;
10
ppm
dietary
burden;
D277089,
T.
Bloem,
16­
Aug­
2001).
Residue
identification
was
performed
via
retention
time
comparison
with
a
mixed
standard
containing
bifenazate,
D3598,
A1530,
A1530­
sulfate,
D9569,
D9472,
and
D1989.
For
liver
and
fat,
these
analyses
yielded
some
difference
from
those
attained
in
the
original
goat
metabolism
study
but
none
of
which
are
of
concern
to
HED.
For
milk,
the
major
identified
residue
in
the
goat
metabolism
study
was
A1530­
sulfate
(
41%
total
radioactive
residue
(
TRR))
while
in
the
radiovalidation
study
the
major
identified
residue
was
D9569
(
24%
TRR;
A1530­
sulfate
was
included
as
a
reference
standard
but
was
not
identified).
HED
notes
that
the
mixed
reference
standard
resulted
in
D9569
and
A1530­
sulfate
eluting
very
close
to
one
another.

Since
radiovalidation
data
indicated
that
the
magnitude
of
A1530/
A1530­
sulfate
residues
found
using
the
enforcement
method
(
concurrent
recoveries
of
86­
88%)
was
in
agreement
with
the
magnitude
of
the
residue
found
when
using
the
methods
employed
in
the
metabolism
study
(
i.
e.
only
trace
residues
were
identified;
see
46691301.
der.
wpd),
HED
concludes
that
the
original
goat
metabolism
study
misidentified
D9569
as
A1530­
sulfate.
HED
requests
that
the
petitioner
submit
data
confirming
the
current
results.

Magnitude
of
the
Residue
­
Plants:
The
petitioner
submitted
potato
tuber
and
succulentshelled
podded
pea
magnitude
of
the
residue
studies.
The
following
are
summaries
of
these
data.

Tuberous
and
Corm
Vegetables
(
crop
subgroup
1c)
­
Combined
residues
of
bifenazate/
D3598
were
<
0.01­
0.015
ppm
in/
on
potato
tuber
samples
harvested
13­
15
days
following
two
broadcast
spray
applications
at
0.75
lb
ai/
acre
(
2x;
retreatment
interval
(
RTI)
=
13­
14
days;
n=
28)
and
were
<
0.01
ppm
in/
on
potato
tuber
samples
harvested
14
days
following
two
broadcast
spray
applications
at
3.73
lb
ai/
acre
(
10x;
RTI
=
13
days;
n=
2).

Based
on
Tables
3
and
5
of
OPPTS
860.1500,
an
additional
potato
field
trial
in
Region
11
is
needed
to
fulfill
the
requested
geographical
distribution
to
support
a
crop
subgroup
1c
registration.
In
addition,
the
potato
storage
stability
data
indicate
that
residues
may
have
declined
83­
89%
during
the
interval
from
harvest
to
analysis.
However,
HED
concludes
that
that
the
currently­
available
data
indicate
that
a
0.10
ppm
tolerance
for
the
combined
residues
of
bifenazate
and
D3598
in/
on
the
tuberous
and
corm
vegetables
is
acceptable
for
the
following
reasons
(
no
additional
data
are
required):
(
1)
all
of
the
field
trials
were
conducted
at
2x
the
proposed
seasonal
rate
and
resulted
in
residues
 
0.015
ppm;
(
2)
the
exaggerated
rate
field
trial
(
10x
the
proposed
seasonal
rate)
resulted
in
residues
<
LOQ
(
limit
of
quantitation);
and
(
3)
the
radish
metabolism
study
result
in
TRRs
in
the
root
of
 
0.0043
ppm
(
1
x
0.75
lb
ai/
acre;
7­
day
PHI).
A
revised
Section
F
is
requested.

Succulent
Shelled/
Podded
Pea
­
Combined
residues
of
bifenazate/
D3598
were
0.028­
0.173
ppm
in/
on
succulent­
shelled
pea
(
n=
12)
and
were
0.91­
3.74
ppm
in/
on
edible­
podded
pea
samples
(
n=
10)
harvested
2­
4
days
following
two
broadcast
spray
applications
at
0.75
lb
ai/
acre
(
3x;
RTI
=
12­
14
days;
n=
28).
Bifenazate
(
000586)
Residue
Chemistry
Summary
D324430
page
4
of
16
The
succulent­
shelled
pea
and
edible­
podded
pea
residue
data
were
conducted
with
application
rates
1.5x
the
single
application
rate
and
3.0x
the
seasonal
application
rate.
As
a
result,
these
data
are
not
indicative
of
the
magnitude
of
the
residue
following
application
at
the
proposed
rate.
Therefore,
HED
requests
that
the
petitioner
submit
succulent­
shelled
pea
(
Regions
1
or
2
(
n=
1),
5
(
n=
3),
11(
n=
1),
and
12
(
n=
1))
and
edible­
podded
pea
(
n=
3;
Regions
at
the
discretion
of
the
petitioner)
field
trial
data
conducted
at
the
proposed
rate
(
storage
stability
data
supporting
the
relevant
storage
intervals
should
also
be
submitted).
Provided
the
petitioner
agrees
to
submit
these
data,
HED
concludes
that
the
available
data
support
a
tolerance
for
the
combined
residues
of
bifenazate
and
D3598
in/
on
succulent
garden­
pea
and
edible­
podded
pea
of
0.20
ppm
and
4.0
ppm,
respectively.
A
revised
Section
F
is
requested.

Magnitude
of
the
Residue
­
Livestock:
Cattle,
goat,
hog,
horse,
and
sheep
meat
(
0.02
ppm),
meat
byproduct
(
0.02
ppm),
and
fat
(
0.10
ppm)
tolerances
are
currently
established;
a
milk
(
0.01
ppm)
tolerance
is
also
currently
established.
Poultry
tolerances
are
not
currently
established.
These
ruminant
tolerances
are
derived
form
secondary
residues
resulting
from
the
wet
apple
pomace
(
1.2
ppm)
and
cotton
gin
byproduct
(
20
ppm)
tolerances.

The
only
feed
items
associated
with
the
current
petition
are
potato
culls
and
processed
potato
waste
(
ruminant
feed
commodities;
no
poultry
feed
commodities).
Based
on
the
wet
apple
pomace
and
cotton
gin
byproduct
tolerances
and
the
recommended
tuberous
and
corm
vegetable
tolerance
of
0.02
ppm,
HED
concludes
that
the
contribution
to
the
dietary
burden
from
the
currently­
requested
crops
is
minimal
and
adjustment
in
the
livestock
tolerances
are
unnecessary.

Residues
in
Rotational
Crops:
A
confined
rotational
crop
study
has
been
previously
submitted
and
reviewed
(
D277089,
T.
Bloem,
16­
Aug­
2001;
field
rotational
crop
study
has
not
been
submitted).
The
MARC
concluded
that
residues
of
concern
in/
on
rotational
crops
could
not
be
determined
from
the
available
data
(
D276801,
T.
Bloem,
16­
Aug­
2001).
On
the
basis
of
the
confined
rotational
crop
study
and
the
proposed
maximum
seasonal
application
rates,
HED
concludes
that
a
30­
day
PBI
for
the
currently­
requested
crops
is
appropriate.

Analytical
Enforcement
Method
­
Plants:
A
method
is
available
for
enforcement
of
the
currentlyestablished
plant
tolerances
(
D281973,
T.
Bloem,
29­
Aug­
2002;
D281979,
T.
Bloem,
29­
Aug­
2002).
The
methods
used
in
the
field
trial
and
processing
studies
were
similar
to
the
current
enforcement
method
(
D281973,
T.
Bloem,
29­
Aug­
2002;
D281979,
T.
Bloem,
29­
Aug­
2002).
Since
the
procedures
are
similar
and
adequate
method
validation
and
concurrent
recoveries
were
attained
in
the
field
trial
and
processing
studies,
HED
concludes
that
the
current
enforcement
method
is
appropriate
for
enforcement
of
the
tolerances
associated
with
this
petition.
Bifenazate
(
000586)
Residue
Chemistry
Summary
D324430
page
5
of
16
Recommendations
Provided
the
petitioner
submits
revised
Sections
B
and
F,
HED
concludes
that
the
residue
chemistry
database
is
sufficient
for
a
conditional
registration
and
establishment
of
the
following
tolerances
for
the
combined
residues
of
bifenazate
and
D3598
(
expressed
as
bifenazate;
a
human­
health
risk
assessment
will
be
prepared
as
a
separate
document):

pea,
garden,
succulent
.........................................................................................................
0.20
ppm
pea,
edible
podded,
succulent
................................................................................................
4.0
ppm
vegetable,
tuberous
and
corm,
subgroup
1c
.........................................................................
0.10
ppm
The
residue
chemistry
database
may
be
suitable
for
unconditional
registration
upon
the
submission
of
data
addressing
the
following
deficiency.

 
succulent­
shelled
pea
(
Regions
1
or
2
(
n=
1),
5
(
n=
3),
11(
n=
1),
and
12
(
n=
1))
and
edible­
podded
pea
(
n=
3;
Regions
at
the
discretion
of
the
petitioner)
field
trial
data
(
storage
stability
data
validating
the
relevant
intervals
should
also
be
submitted)
Bifenazate
(
000586)
Residue
Chemistry
Summary
D324430
page
6
of
16
Detailed
Considerations
Background
Bifenazate
is
a
selective
miticide
which
controls
the
motile
stage
of
mites
either
by
direct
contact
or
through
contact
with
foliar
residues.
The
petitioner
indicated
that
bifenazate
blocks
or
closes
the
gamma­
aminobutyric
acid
(
GABA)
activated
chloride
channels
of
susceptible
pests
resulting
in
overexcitation
of
the
peripheral
nervous
system.

Table
1:
Test
Compound
Nomenclature.

Compound
O
NH
N
H
O
CH
3
O
CH
3
CH
3
Common
name
Bifenazate
Company
experimental
name
D2341
IUPAC
name
isopropyl
2­(
4­
methoxy­
1,1'­
biphenyl­
2­
yl)
hydrazinecarboxylate
CAS
name
hydrazine
carboxylic
acid,
2­(
4­
methoxy­[
1,1'­
biphenyl]­
3­
yl),
1­
methylethyl
ester
CAS
registry
number
149877­
41­
8
End­
use
products
(
EPs)
AcramiteTM
50WS
(
50%
WP;
EPA
Reg.
No.
400­
503)

Table
2:
Physicochemical
Properties
of
the
Technical
Grade
of
Bifenazate.

Melting
range
124­
125
º
C
pH
6.78
Density
1.19
g/
cm3
Water
solubility
2.1
mg/
L
(
20
°
C)

Solvent
solubility
102
mg/
mL
ethyl
acetate
(
20
°
C)

Vapor
pressure
<
1
x
10­
8
atm
M3/
mole
(
25
°
C)

Dissociation
constant,
pKa
12.94
at
23
°
C
Octanol/
water
partition
coefficient,
Log(
KOW)
3.4
UV/
visible
absorption
spectrum
Max
264
nm
in
water
MRID
46064101
Bifenazate
(
000586)
Residue
Chemistry
Summary
D324430
page
7
of
16
860.1200
Directions
for
Use
The
petitioner
proposed
single
foliar
applications
of
Acramite
®
­
4SC
(
4
lb
ai/
gal;
EPA
Reg.
No.
­
400­
514)
succulent
pea
and
tuberous
and
corm
vegetables
(
crop
subgroup
1c).
The
proposed
label
indicates
that
application
through
irrigation
equipment
is
prohibited
and
does
not
include
rotational
crop
restrictions.
Table
3
is
a
summary
of
the
proposed
application
scenario.

The
submitted
label
adequately
describes
the
proposed
application
scenarios.
Based
on
the
current
rotational
crop
data,
HED
concludes
that
a
30­
day
rotational
crop
restriction
is
appropriate
for
all
nonlabeled
crops
(
labeled
crops
may
be
planted
at
anytime;
see
section
OPPTS
860.1850).
A
revised
Section
B
is
requested.

Table
3:
Proposed
Application
Scenarios
Formulation
Crop
App.
Rate
(
lb
ai/
acre)
PHI1
(
days)
Comments
tuberous
and
corm
vegetables
(
crop
subgroup
1c)
2
1x
0.50­
0.75
14
­
apply
with
ground
(
min
20
gallons
per
acre
(
GPA))
or
aerial
(
min
5
GPA)
equipment
­
do
not
apply
more
than
one
application
per
year
4
lb
ai/
gal
SC
succulent
pea
1x
0.38­
0.50
14
­
apply
with
ground
(
min
20
GPA)
or
aerial
(
min
5
GPA)
equipment
­
do
not
apply
more
than
one
application
per
year
1
PHI
=
preharvest
interval
2
arracacha,
arrowroot,
Chinese
artichoke,
Jerusalem
artichoke,
edible
canna,
cassava,
bitter
and
sweet
chayote
(
root),
chufa,
dasheen
(
taro),
ginger,
leren,
potato,
sweet
potato,
tanier,
yam
bean,
true
yam
860.1300
Nature
of
the
Residue
­
Plants
Based
on
apple,
orange,
and
cotton
metabolism
studies,
the
MARC
determined
that
for
tolerance
expression
and
risk
assessment
purposes,
the
residues
of
concern
in
these
crops
are
bifenazate
and
D3598
(
D276801,
T.
Bloem,
16­
Aug­
2001).
The
metabolic
route
in
apple,
orange,
and
cotton
were
similar
and
proceeded
via
oxidation
of
the
hydrazine
moiety
of
bifenazate
to
form
D3598
which
is
further
degraded
to
D1989,
D9963,
D4642,
and/
or
A1530
and
to
bound
residues
by
reaction
with
natural
products.
The
MARC
did
discuss
the
possible
formation
of
hydrazine
in
plants
and
concluded
that
formation
of
hydrazine
is
unlikely
due
to
the
oxidation
of
the
parent
to
the
conjugated
diazene.
However,
the
MARC
suggested
that
if
the
petitioner
submits
additional
metabolism
studies,
the
presence
of
biphenyl
hydrazine
should
be
monitored
as
a
confirmatory
measure.

Subsequent
to
this
decision,
a
radish
metabolism
study
was
submitted.
Radish
plants
were
treated
with
single
spray
application
of
bifenazate
at
0.375
or
0.75
lb
ai/
acre
(
soil
was
added
to
cover
exposed
root
prior
to
application)
and
mature
root
and
top
samples
were
harvested
7
days
after
application
(
TRRs;
top
­
13.0
ppm
(
0.375
lb
ai/
acre)
and
26.4
ppm
(
0.75
lb
ai/
acre);
root
­
0.0023
ppm
(
0.375
lb
ai/
acre)
and
0.0043
ppm
(
0.75
lb
ai/
acre)).
No
further
analytical
work
was
performed
in/
on
the
radish
root
samples
since
the
TRRs
were
<
0.01
ppm.
Analysis
of
the
radish
tops
indicated
that
bifenazate
and
D3598
were
the
major
residues
(
hydroxylated
D3598
and
D23­
03
were
also
identified;
biphenyl
hydrazine
was
included
as
a
reference
standard
put
was
not
identified).

The
petitioner
has
submitted
metabolism
studies
on
radish,
apple,
orange,
and
cotton.
The
metabolic
Bifenazate
(
000586)
Residue
Chemistry
Summary
D324430
page
8
of
16
route
in
all
crops
were
similar
with
major
residues
being
comprised
of
bifenazate
and
D3598.
Since
metabolism
studies
on
three
diverse
crops
have
been
submitted
and
the
metabolic
route
were
similar,
HED
concludes
that
the
nature
of
the
residue
in
plants
understood
and
the
residues
of
concern
for
tolerance
expression
and
risk
assessment
purposes
are
bifenazate
and
D3598.

OPPTS
GLN
860.1300:
Nature
of
the
Residue
­
Livestock
The
MARC
reviewed
goat
and
hen
metabolism
studies
and
determined
that
for
tolerance
expression
and
risk
assessment
purposes,
the
residues
of
concern
in
livestock
tissue
(
excluding
fat),
eggs,
and
milk
are
bifenazate,
D3598
(
expressed
as
bifenazate),
A1530,
and
A1530­
sulfate
(
expressed
as
A1530).
The
residues
of
concern
for
tolerance
expression
and
risk
assessment
purposes
in
fat
are
bifenazate
and
D3598
(
expressed
as
bifenazate).
The
metabolic
route
in
goats
and
hens
were
similar
and
proceeded
via
oxidation
of
the
hydrazine
moiety
of
bifenazate
to
form
D3598
which
is
further
degraded
to
D1989,
D9569,
A1530,
and/
or
A1530
­
sulfate
and
to
bound
residues
by
reaction
with
natural
products
(
D276801,
T.
Bloem,
16­
Aug­
2001).

Subsequent
to
this
decision,
the
petitioner
submitted
a
radiovalidation
study
which,
for
purposes
of
sample
generation,
dosed
goats
with
14C­
bifenazate
uniformly
labeled
in
the
o­
methyl
phenyl
ring
for
four
consecutive
days
(
20­
ppm
daily
dietary
burden).
Milk,
liver,
and
fat
samples
were
collected,
extracted
with
a
variety
of
solvents,
and
analyzed
using
the
same
methods
employed
in
the
goat
metabolism
study
(
lactating
goat;
10
ppm
dietary
burden;
D277089,
T.
Bloem,
16­
Aug­
2001).
Residue
identification
was
performed
via
retention
time
comparison
with
a
mixed
standard
containing
bifenazate,
D3598,
A1530,
A1530­
sulfate,
D9569,
D9472,
and
D1989.
For
liver
and
fat,
these
analyses
yielded
some
difference
from
those
attained
in
the
original
goat
metabolism
study
but
none
of
which
are
of
concern
to
HED.
For
milk,
the
major
identified
residue
in
the
goat
metabolism
study
was
A1530­
sulfate
(
41%
TRR)
while
in
the
radiovalidation
study
the
major
identified
residue
was
D9569
(
24%
TRR;
A1530­
sulfate
was
included
as
a
reference
standard
but
was
not
identified).
HED
notes
that
the
mixed
reference
standard
resulted
in
D9569
and
A1530­
sulfate
eluting
very
close
to
one
another.

Since
radiovalidation
data
indicated
that
the
magnitude
of
A1530/
A1530­
sulfate
residues
found
using
the
enforcement
method
(
concurrent
recoveries
of
86­
88%)
was
in
agreement
with
the
magnitude
of
the
residue
found
when
using
the
methods
employed
in
the
metabolism
study
(
i.
e.
only
trace
residues
were
identified;
see
46691301.
der.
wpd),
HED
concludes
that
the
original
goat
metabolism
study
misidentified
D9569
as
A1530­
sulfate.
HED
requests
that
the
petitioner
submit
data
confirming
the
current
results.
Bifenazate
(
000586)
Residue
Chemistry
Summary
D324430
page
9
of
16
OPPTS
GLN
860.1340:
Residue
Analytical
Method
­
Plants
The
methods
used
in
the
magnitude
of
the
residue
studies
were
adequately
validated
and
are
appropriate
for
data
collection
purposes.
These
methods
are
similar
to
the
current
analytical
enforcement
method
(
method
does
not
distinguish
between
bifenazate
and
D3598;
LOQ
=
0.01
ppm;
D281973,
T.
Bloem,
29­
Aug­
2002;
D281979,
T.
Bloem,
29­
Aug­
2002).
Since
the
procedures
are
similar
and
adequate
concurrent
recoveries
were
attained
in
the
magnitude
of
the
residue
studies,
HED
concludes
that
the
current
enforcement
method
is
appropriate
for
enforcement
of
the
tolerances
associated
with
this
petition.

OPPTS
GLN
860.1360:
Multiresidue
Method
HED
reviewed
the
petitioner
submitted
Food
and
Drug
Administration
(
FDA)
Multireresidue
Method
studies
for
bifenazate,
D3598,
A1530,
and
A1530­
sulfate.
These
data
indicate
that
bifenazate,
D3598,
A1530,
and
A1530­
sulfate
are
not
quantitatively
recovered
through
the
FDA
Multiresidue
Methods.
The
following
is
a
summary
of
these
data.

Bifenazate
and
D3598:
The
petitioner
submitted
data
concerning
the
recovery
of
bifenazate
and
D3598
using
FDA
multiresidue
method
protocols
A,
C,
D,
E,
and
F
(
D277089,
T.
Bloem,
16­
Aug­
2001).
These
data
were
forwarded
to
FDA
(
D273067,
T.
Bloem,
6­
Mar­
2001).
Due
to
instability
in
methanol,
neither
compound
could
be
accurately
quantified
using
Protocol
A.
Gas
chromatographic
systems
equipped
with
a
DB­
1
type
column
and
either
an
ECD
or
NPD
detector
gave
acceptable
results
for
both
compounds
(
Protocol
C).
Recovery
from
apples
using
Protocol
D
without
Florisil
cleanup
resulted
in
recoveries
of
 
43%.
Testing
using
Protocols
E
and
F
Florisil
cleanup
systems
resulted
in
recoveries
of
<
30%.

A1530
and
A1530­
sulfate:
The
petitioner
also
submitted
concerning
the
recovery
of
A1530
and
A1530­
sulfate
using
FDA
multiresidue
method
protocols
A,
B,
C,
and/
or
D
(
D313261,
T.
Bloem,
5­
July­
2006).
These
data
were
forwarded
to
the
FDA
(
D328815,
T.
Bloem,
17­
May­
2006).

A1530
was
tested
through
Protocols
A,
B,
C,
and
D;
because
the
test
substance
is
not
a
substituted
urea,
testing
under
Protocol
G
is
not
required.
Protocol
A
testing
indicated
that
A1530
is
naturally
fluorescent,
but
the
compound
was
not
recovered
from
the
charcoal/
celite
cleanup
column.
Under
Protocol
B,
the
methyl
ether
of
A1530
was
not
detected
using
a
gas
chromatograph/
electron­
capture
detector
(
GC/
ECD)
system.
Metabolite
A1530
chromatographed
(
GC/
ECD)
with
a
reasonable
relative
retention
time
and
acceptable
sensitivity
through
Level
I
testing
of
Protocol
C.
However,
A1530
was
not
recovered
under
the
conditions
of
Module
DG6
of
Protocol
D
testing;
therefore,
further
testing
through
Protocols
D,
E,
and
F
was
not
conducted.

A1530­
S
was
tested
through
Protocols
A
and
C;
because
the
test
substance
is
not
an
acid
or
a
phenol
or
a
substituted
urea,
testing
under
Protocols
B
and
G
is
not
required.
Protocol
A
testing
indicated
that
A1530­
S
is
naturally
fluorescent,
but
the
compound
was
converted
to
A1530
and
was
not
recovered
from
the
charcoal/
Celite
cleanup
column.
Level
I
testing
through
Protocol
C
indicated
that
A1530­
S
is
partially
converted
to
A1530
and
does
not
pass
intact
through
GC
analysis;
therefore,
further
testing
through
Protocols
C,
D,
E,
and
F
was
not
conducted.
Bifenazate
(
000586)
Residue
Chemistry
Summary
D324430
page
10
of
16
OPPTS
GLN
860.1380:
Storage
Stability
Data
Table
4
is
a
summary
of
the
currently­
available
storage
stability
data.
HED
notes
that
some
of
the
storage
stability
studies
were
conducted
for
only
bifenazate
(
bifenazate
and
D3598
are
the
residues
of
concern
for
risk
assessment
and
tolerance
enforcement).
D3598
was
not
a
major
residue
identified
in
the
plant
metabolism
studies
( 
6%
TRR)
and
was
included
as
a
residue
of
concern
only
because
the
analytical
method
did
not
distinguish
between
bifenazate
and
D3598
(
D276623,
T.
Bloem,
31­
Jul­
2001;
D276801,
T.
Bloem,
16­
Aug­
2001;
D290053,
T.
Bloem,
29­
May­
2003).
Therefore,
plant
storage
stability
data
for
D3598
are
not
necessary.

The
potato
magnitude
of
the
residue
study
employed
a
storage
interval
of
4­
15
days.
Based
on
the
potato
storage
stability
data
submitted
with
this
petition,
HED
concludes
that
significant
decline
in
residues
may
have
occurred
in
potato
during
storage
(
46651702.
der.
doc;
see
below
for
summary).
The
succulent
pea
magnitude
of
the
residue
study
employed
a
storage
interval
of
 
30
days.
Since
the
currently
available
data
indicate
that
residue
of
bifenazte
are
unstable
in
some
matrices
when
stored
frozen
for
intervals
<
30
days,
HED
requests
that
the
petitioner
submit
succulent
pea
storage
stability
data
validating
this
interval.

46651702.
der.
doc
(
potato
storage
stability
data):
Potato
tuber
samples
were
fortified
on
the
skin
with
bifenazate
at
0.1
ppm.
The
samples
were
homogenized
and
placed
in
frozen
storage
for
7,
14,
and
28
days
and
were
analyzed
for
residues
of
bifenazate
using
an
adequately­
validated
method.
The
average
percent
recovery
of
bifenazate
at
time
zero
was
83%
(
n=
1).
The
average
corrected
percent
recovery
(
corrected
for
concurrent
recovery
and
residues
in/
on
controls)
after
7
(
n=
3),
14
(
n=
3),
and
28
(
n=
3)
days
of
storage
was
15%,
11%,
and
17%,
respectively.

Table
4:
Storage
Stability
Data
Crop
Resdiue
Interval
Reference
cantaloupe
bifenazate
2
months
46024201.
der.
wpd
tomato
bifenazate
5
months
46024203.
der.
wpd
tomato
paste
bifenazate
1
month
tomato
puree
bifenazate
1
month
46555001.
der.
wpd
mint
foliage
bifenazate
2.5
months
45971701.
der.
wpd
pepper
bifenazate
5
months
46024202.
der.
wpd
apple
bifenazate
and
D3598
42
days
grape
bifenazate
and
D3598
7
days
peach
bifenazate
and
D3598
56
days
­
bifenazate
14
days
­
D3598
cottonseed
bifenazate
and
D3598
<
21
days1
cotton
gin
byproducts
bifenazate
and
D3598
<
44
days1
cottonseed
hulls
bifenazate
and
D3598
52
days
cottonseed
oil
bifenazate
and
D3598
28
days
cottonseed
meal
bifenazate
and
D3598
43
days
­
bifenazate
<
43
days
­
D35981
D277089,
T.
Bloem,
16­
Aug­
2001
potato
bifenazate
<
7
days
46651702.
der.
doc
1
shortest
interval
tested
Bifenazate
(
000586)
Residue
Chemistry
Summary
D324430
page
11
of
16
OPPTS
GLN
860.1480:
Meat/
Milk/
Poultry/
Eggs
Cattle,
goat,
hog,
horse,
and
sheep
meat
(
0.02
ppm),
meat
byproduct
(
0.02
ppm),
and
fat
(
0.1
ppm)
tolerances
are
currently
established;
a
milk
(
0.01
ppm)
tolerance
is
also
currently
established.
Poultry
tolerances
are
not
currently
established.
These
ruminant
tolerances
are
derived
from
secondary
residues
resulting
from
the
wet
apple
pomace
(
1.2
ppm)
and
cotton
gin
byproduct
(
20
ppm)
tolerances.

The
only
feed
items
associated
with
the
current
petition
are
potato
culls
and
processed
potato
waste
(
ruminant
feed
commodities;
no
poultry
feed
commodities).
Based
on
the
wet
apple
pomace
and
cotton
gin
byproduct
tolerances
and
the
recommended
tuberous
and
corm
vegetable
tolerance
of
0.02
ppm,
HED
concludes
that
the
contribution
to
the
dietary
burden
from
the
currently
requested
crops
is
minimal
and
adjustment
in
the
livestock
tolerances
is
unnecessary.

OPPTS
GLN
860.1500:
Crop
Field
Trials
46651701.
der.
doc;
46651703.
der.
doc
The
following
paragraphs
and
Table
5
are
summaries
of
the
potato
and
succulent
pea
field
trial
data
submitted
in
support
of
the
current
petition.

Tuberous
and
Corn
Vegetables
(
crop
subgroup
1c):
A
total
of
15
potato
field
trials
were
conducted
during
the
2002
growing
season
in
Regions
1
(
n=
2),
2
(
n=
1),
3
(
n=
1),
5
(
n=
4),
9
(
n=
1),
10
(
n=
1),
and
11
(
n=
5).
Each
field
trial
consisted
of
a
control
and
treated
plot.
The
treated
plot
received
two
broadcast
spray
applications
of
the
4
lb
ai/
gal
SC
bifenazate
formulation
(
Acramite
®
4L
SC;
EPA
Reg.
No.
400­
514)
at
0.75
lb
ai/
acre
(
RTI
14
days).
At
one
of
the
sites,
only
a
single
application
was
made
due
to
excessive
heat
and
lack
in
rainfall
late
in
the
season
which
caused
vine
desiccation.
In
addition,
at
one
of
the
sites
a
second
treated
plot
was
established
which
received
two
broadcast
spray
applications
of
the
4
lb
ai/
gal
SC
bifenazate
formulation
at
3.73
lb
ai/
acre
(
14­
day
RTI).
All
applications
were
broadcast
sprays
and
were
made
using
ground
equipment
in
18­
78
GPA.
A
surfactant
(
Silwet
®
)
was
added
to
most
of
the
spray
mixtures.
Mature
potato
tubers
were
harvested
13­
15
days
after
the
final
application.

The
potato
tuber
samples
were
analyzed
for
combined
residues
of
bifenazate
and
its
metabolite
D3598
using
a
high­
performance
liquid
chromatograph
(
HPLC)
method
with
oxidative
coulometric
electrochemical
detection.
The
validated
LOQ
was
0.01
ppm.
This
method
is
essentially
the
same
as
the
enforcement
method
for
the
currently­
established
plant
tolerances
(
D281973,
T.
Bloem,
29­
Aug­
2002).
This
method
is
adequate
for
data
collection
based
on
acceptable
concurrent
method
recoveries
from
potato
tubers
fortified
at
0.01­
0.05
ppm
(
residue
in/
on
controls
were
nondetect­
0.003
ppm).

The
potato
tuber
samples
were
stored
frozen
from
harvest
to
extraction
for
4­
15
days.
The
currently­
available
storage
stability
data
indicate
the
bifenazate
residues
declined
83­
89%
after
7
days
of
frozen
storage
(
shortest
interval
tested;
46651702.
der.
wpd).
Based
on
these
data,
HED
concludes
that
significant
decline
in
bifenazate
residues
may
have
occurred.
HED
notes
that
the
storage
stability
data
were
for
bifenazate
only
(
D3598
data
were
not
included).
However,
D3598
was
not
a
major
residue
identified
in
the
apple,
orange,
cotton,
and
radish
metabolism
studies
( 
6%
Bifenazate
(
000586)
Residue
Chemistry
Summary
D324430
page
12
of
16
TRRs)
and
was
included
as
a
residue
of
concern
only
because
the
analytical
method
did
not
distinguish
between
bifenazate
and
D3598
(
D276623,
T.
Bloem,
31­
Jul­
2001;
D276801,
T.
Bloem,
16­
Aug­
2001;
D290053,
T.
Bloem,
29­
May­
2003).
Therefore,
storage
stability
data
for
D3598
are
not
necessary.

Combined
residues
of
bifenazate/
D3598
were
<
0.01­
0.015
ppm
in/
on
potato
tuber
samples
harvested
13­
15
days
following
two
broadcast
spray
applications
at
0.75
lb
ai/
acre
(
RTI
=
13­
14
days;
n=
28).
Combined
residues
of
bifenazate/
D3598
were
<
0.01
ppm
in/
on
potato
tuber
samples
harvested
14
days
following
two
broadcast
spray
applications
at
3.73
lb
ai/
acre
(
RTI
=
13
days;
n=
2)
and
were
<
0.01
ppm
in/
on
potato
tuber
samples
harvested
14
days
following
a
single
broadcast
spray
application
at
0.75
lb
ai/
acre
(
n=
2).

Conclusion:
Based
on
Tables
3
and
5
of
OPPTS
860.1500,
an
additional
potato
field
trial
in
Region
11
is
needed
to
fulfill
the
requested
geographical
distribution
to
support
a
crop
subgroup
1c
registration.
In
addition,
the
potato
storage
stability
data
indicate
that
residues
may
have
declined
83­
89%
during
the
interval
from
harvest
to
analysis.
However,
HED
concludes
that
that
the
currently­
available
data
indicate
that
a
0.10
ppm
tolerance
for
the
combined
residues
of
bifenazate
and
D3598
in/
on
the
tuberous
and
corm
vegetables
is
acceptable
for
the
following
reasons
(
no
additional
data
are
required):
(
1)
all
of
the
field
trials
were
conducted
at
2x
the
proposed
seasonal
rate
and
resulted
in
residues
 
0.015
ppm;
(
2)
the
exaggerated
rate
field
trial
(
10x
the
proposed
seasonal
rate)
resulted
in
residues
<
LOQ;
and
(
3)
the
radish
metabolism
study
result
in
TRRs
in
the
root
of
 
0.0043
ppm
(
1
x
0.75
lb
ai/
acre;
7­
day
PHI).
A
revised
Section
F
is
requested.

Succulent
Pea:
A
total
of
5
succulent­
shelled
pea
field
trials
were
conducted
during
the
2002
growing
season
in
Regions
2
(
n=
2),
5
(
n=
1),
11
(
n=
1),
and
12
(
n=
1)
and
total
of
4
edible­
podded
pea
field
trials
were
conducted
during
the
2002
growing
season
in
Regions
2
(
n=
1),
5
(
n=
1),
10
(
n=
1),
and
11
(
n=
1).
Each
field
trial
consisted
of
a
control
and
treated
plot.
The
treated
plot
received
two
broadcast
spray
applications
of
the
4
lb
ai/
gal
SC
bifenazate
formulation
(
Acramite
®
4L
SC;
EPA
Reg.
No.
400­
514)
at
0.75
lb
ai/
acre
(
RTI
=
12­
14
days).
All
applications
were
broadcast
sprays
and
were
made
using
ground
equipment
in
24­
52
GPA.
Mature
succulent­
shelled
pea
and
edible­
podded
pea
were
harvested
2­
4
days
after
the
final
application.

The
samples
were
analyzed
for
combined
residues
of
bifenazate
and
its
metabolite
D3598
using
a
HPLC
method
with
oxidative
coulometric
electrochemical
detection
(
see
attachment
1
for
structures).
The
validated
LOQ
was
0.01
ppm.
This
method
is
essentially
the
same
as
the
enforcement
method
for
the
currently­
established
plant
tolerances
(
D281973,
T.
Bloem,
29­
Aug­
2002).
This
method
is
adequate
for
data
collection
based
on
acceptable
concurrent
method
recoveries
from
control
samples
fortified
at
0.01­
5.0
ppm
(
residue
in/
on
controls
were
nondetect­
0.008
ppm).

The
samples
were
stored
frozen
from
harvest
to
extraction
for
 
30
days
(
samples
were
analyzed
within
one
day
of
extraction).
The
currently­
available
storage
stability
data
indicate
the
bifenazate
and/
or
D3598
are
not
stable
in/
on
some
matrices
when
stored
frozen
for
intervals
of
<
30
days
(
D277089,
T.
Bloem,
16­
Aug­
2001).
Based
on
these
data
and
since
HED
does
not
have
storage
stability
data
in/
on
a
legume
vegetable,
HED
concludes
that
the
storage
intervals
have
not
been
validated.
Bifenazate
(
000586)
Residue
Chemistry
Summary
D324430
page
13
of
16
Combined
residues
of
bifenazate/
D3598
were
0.028­
0.173
ppm
in/
on
succulent­
shelled
pea
(
n=
12)
and
were
0.91­
3.74
ppm
in/
on
edible­
podded
pea
samples
(
n=
10)
harvested
2­
4
days
following
two
broadcast
spray
applications
at
0.75
lb
ai/
acre
(
RTI
=
12­
14
days;
n=
28).

Conclusion:
The
succulent­
shelled
pea
and
edible­
podded
pea
residue
data
were
conducted
with
application
rates
1.5x
the
single
application
rate
and
3.0x
the
seasonal
application
rate.
Therefore,
these
data
are
not
indicative
of
the
magnitude
of
the
residue
following
application
at
the
proposed
rate.
As
a
result,
HED
requests
that
the
petitioner
submit
succulent­
shelled
pea
(
Regions
1
or
2
(
n=
1),
5
(
n=
3),
11(
n=
1),
and
12
(
n=
1))
and
edible­
podded
pea
(
n=
3;
Regions
at
the
discretion
of
the
petitioner)
field
trial
data
conducted
at
the
proposed
rate
(
storage
stability
data
validating
the
relevant
intervals
should
also
be
submitted).
Provided
the
petitioner
agrees
to
submit
these
data,
HED
concludes
that
the
available
data
support
a
tolerance
for
the
combined
residues
of
bifenazate
and
D3598
in/
on
succulent
garden­
pea
and
edible­
podded
pea
of
0.20
ppm
and
4.0
ppm,
respectively.
A
revised
Section
F
is
requested.
Since
the
currently­
available
succulent
pea
residue
data
were
conducted
at
3.0x
the
proposed
rate
and
since
these
data
are
being
used
in
the
interim
until
a
complete
set
of
succulent
pea
field
trial
data
conducted
at
1x
is
submitted,
HED
concluded
that
use
of
the
tolerance
spreadsheet
was
unnecessary
(
the
tolerance
spreadsheet
will
be
used
for
the
1x
data).

Table
5.
Summary
of
Residue
Data.

Combined
Bifenazate/
D3598
Residue
Levels
(
ppm)
Commodity
Total
App.
Rate
(
lb
ai/
acre)
PHI
(
days)
n
Min.
Max.
HAFT
1
Median
Mean
Std.
Dev.

succulent­
shelled
pea
2
x
0.75
2­
4
12
0.028
0.173
0.132
0.038
0.060
0.043
edible­
podded
pea
2
x
0.75
2­
4
10
0.91
3.74
3.08
1.51
1.99
0.99
potato
tuber
2
x
0.75
13­
15
28
<
0.01
0.015
0.012
<
0.01
<
0.01
­­
1
HAFT
=
Highest
Average
Field
Trial.

860.1520
Processed
Food
and
Feed
46651701.
der.
doc
The
only
processed
commodity
associated
with
the
current
petition
is
processed
potato
waste.
The
potato
magnitude
of
the
residue
study
included
a
field
trial
which
was
treated
with
2
applications
of
bifenazate
at
3.73
lb
ai/
acre
(
14­
day
RTI;
5x
the
single
application
rate
and
10x
the
seasonal
application
rate).
The
potato
tubers
were
harvested
14
days
after
the
final
application.
Residues
of
bifenazate
and
D3598
were
<
LOQ
in/
on
the
potato
tuber
samples
(
frozen
storage
interval
of
5
days);
therefore,
the
potato
tubers
were
not
processed.
HED
notes
that
the
potato
storage
stability
data
indicated
that
residues
declined
83­
89%
after
7
days
of
storage.
Since
the
radish
metabolism
study
result
in
TRRs
in
the
root
of
 
0.0043
ppm
(
1
x
0.75
lb
ai/
acre;
7­
day
PHI),
HED
concludes
that
the
currently
available
potato
tuber
data
are
acceptable
and
the
tolerances
in
on
potato
tuber
processed
commodities
are
unnecessary.
Bifenazate
(
000586)
Residue
Chemistry
Summary
D324430
page
14
of
16
OPPTS
GLN
860.1850:
Confined
Accumulation
in
Rotational
Crops
A
confined
accumulation
in
rotational
crop
study
has
been
previously
submitted
and
reviewed
by
HED
(
D277089,
T.
Bloem,
16­
Aug­
2001;
field
rotational
crop
study
has
not
been
submitted).
[
14C]
Bifenazate
was
applied
to
bare
soil
in
pots
at
a
rate
equivalent
to
0.5
lb
ai/
acre
or
5.0
lb
ai/
acre
(
0.7x
and
6.7x
the
maximum
seasonal
application
rate
for
the
currently
requested
crops).
The
soil
was
aged
for
30,
125,
and
365
days
and
was
planted
with
carrot,
lettuce,
and
wheat
(
soil
aged
for
365
days
was
only
planted
with
wheat).

The
MARC
reviewed
the
confined
rotational
crop
study
and
concluded
that
residues
of
concern
in/
on
rotational
crops
could
not
be
determined
from
the
available
data
(
D276801,
T.
Bloem,
16­
Aug­
2001).
HED
concludes
that
the
a
30­
day
rotational
crop
restriction
is
appropriate
for
the
following
reasons:
(
1)
application
was
made
to
bare
soil;
(
2)
TRRs
in
mature
carrot
planted
30
days
after
treatment
at
0.50
lb
ai/
acre
were
<
0.01
ppm
(
0.007
ppm);
(
3)
TRRs
in
mature
lettuce
planted
30
days
after
treatment
at
0.50
lb
ai/
acre
were
0.014
ppm.
However,
upon
analysis,
no
residue
>
0.01
ppm
was
identified;
and
(
4)
TRRs
in
and
wheat
forage,
wheat
hay,
wheat
chaff,
and
wheat
grain
planted
30
days
after
treatment
at
0.50
lb
ai/
acre
were
0.038
ppm,
0.117
ppm,
0.031
ppm,
and
0.016
ppm,
respectively;
however,
upon
analysis,
no
residues
>
0.01
ppm
was
identified.

860.1550
Proposed
Tolerances
Table
6
is
a
summary
of
the
proposed
and
recommended
tolerances
for
the
combined
residues
of
Bifenazate
and
D3598.
A
revised
Section
F
is
requested.
There
are
currently
no
established
Codex,
Canadian,
or
Mexican
maximum
residue
limits
(
MRLs)
for
Bifenazate
in/
on
the
proposed
commodities.
Therefore,
harmonization
is
not
an
issue.

Table
6:
Tolerance
Summary
Proposed
HED
Recommended
Commodity
Definition
Tolerance
(
ppm)
Commodity
Definition
Tolerance
(
ppm)

pea,
garden
0.2
pea,
garden,
succulent
0.20
pea,
edible
podded
4.0
pea,
edible
podded,
succulent
4.0
vegetable,
tuberous
and
corm,
subgroup
1c
0.01
vegetable,
tuberous
and
corm,
subgroup
1C
0.10
Attachment
1:
Chemical
Structures
Attachment
2:
IRLS
RDI:
RAB1
Chemists
(
12­
July­
2006)
T.
Bloem:
S10945:
Potomac
Yard:
703­
605­
0217:
7509P:
RAB1
Bifenazate
(
000586)
Residue
Chemistry
Summary
D324430
page
15
of
16
attachment
1:
chemical
structures
chemical
name
chemical
structure
bifenazate
(
D2341)

hydrazinecarboxylic
acid,
2­(
4­
methoxy­[
1,1'­
biphenyl]­
3­
yl),
1­
methylethyl
ester
O
NH
N
H
O
CH
3
O
CH
3
CH
3
D3598
diazinecarboxylic
acid,
2­(
4­
methoxy­[
1,1'­
biphenyl]­
3­
yl),
1­
methylethyl
ester
O
N
N
O
CH
3
O
CH
3
CH
3
D4642
diazinecarboxylic
acid,
2­(
4­
methoxy­[
1,1'­
biphenyl]­
3­
yl),
1­
methylethyl
ester
2­
oxide
OCH3
N
N
O
CH
3
O
CH
3
OH
D9963
4­
methoxy­[
1,1'­
biphenyl]­
3­
ol
OCH3
OH
D1989
1,1'­
biphenyl,
4­
methoxy
OCH3
D9569
[
1,1'­
biphenyl]­
4,4'­
diol
OH
HO
A1530
1,1'­
biphenyl,
4­
ol
OH
A1530­
sulfate
OSO3H
D9472
OH
OH
D23­
14;
biphenyl
hydrazine;
(
4­
methoxy­[
1,1'­
biphenyl]­
3­
yl)
hydrazine
OCH3
NH
NH2
Bifenazate
(
000586)
Residue
Chemistry
Summary
D324430
page
16
of
16
Attachment
2:
IRLS
INTERNATIONAL
RESIDUE
LIMIT
STATUS
Chemical
Name:
hydrazinecarboxylic
acid,
2­(
4­
methoxy­[
1,1'­
biphenyl]­
3­
yl),
1­
methylethyl
ester
Common
Name:

bifenazate
Proposed
tolerance
Reevaluated
tolerance
x
Other
­
recommended
tolerances
Date:
29­
June­
2006
Codex
Status
(
Maximum
Residue
Limits)
U.
S.
Tolerances
No
Codex
proposal
step
6
or
above
X
No
Codex
proposal
step
6
or
above
for
the
crops
requested
Petition
Number:
279­
3181
DP
Barcode:
329605
Other
Identifier:

Reviewer/
Branch:
Tom
Bloem
Residue
definition
(
step
8/
CXL):
bifenazate
Residue
definition:
bifenazate
and
diazinecarboxylic
acid,
2­
(
4­
methoxy­[
1,1'­
biphenyl]­
3­
yl),
1­
methylethyl
ester
Crop
(
s)
MRL
(
mg/
kg)
Crop(
s)
Tolerance
(
ppm)

tuberous
and
corm
vegetable
(
crop
subgroup
1c)
0.01
pea,
garden
0.2
pea,
edible
podded
0.4
Limits
for
Canada
Limits
for
Mexico
X
No
Limits
No
Limits
for
the
crops
requested
X
No
Limits
No
Limits
for
the
crops
requested
Residue
definition:
N/
A
Residue
definition:
N/
A
Crop(
s)
MRL
(
mg/
kg)
Crop(
s)
MRL
(
mg/
kg)

Notes/
Special
Instructions:
S.
Funk,
07/
03/
2006
