Document ID: EPA-HQ-OPP-2006-0103-0004
Agency: epa
Document Type: Supporting & Related Material
Title: 
Posted Date: 2006-03-15T05:00Z

UNITED
STATES
ENVIRONMENTAL
PROTECTION
AGENCY
WASHINGTON,
D.
C.
20460
OFFICE
OF
PREVENTION,
PESTICIDES
AND
TOXIC
SUBSTANCES
MEMORANDUM
Date:
18­
MAY­
2005
Subject:
Triflumizole.
Section
3
Request
for
Use
on
Filberts.
Summary
of
Analytical
Chemistry
and
Residue
Data.

DP#:
D312293
Decision
#:
352810
PC
Code:
128879
PP#:
3E6535
40
CFR
§
180.476
MRID#:
45810201
From:
Jennifer
R.
Tyler,
Chemist
Registration
Action
Branch
(
RAB1)
Health
Effects
Division
(
HED)
(
7509C)

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

To:
Sidney
Jackson/
Robert
Forrest,
PM
Team
05
Registration
Division
(
RD)
(
7505C)

The
Interregional
Research
Project
Number
4
(
IR­
4)
has
submitted
a
petition
for
the
establishment
of
a
permanent
tolerance
for
residues
of
the
fungicide
triflumizole,
[
1­((
4­
chloro­
2­
(
trifluoromethyl)
phenyl)
imino­
2­
propoxyethyl]­
1H­
imidazole,
and
its
metabolites
containing
the
4­
chloro­
2­
trifluoromethylaniline
moiety,
calculated
as
the
parent
compound,
in/
on
filbert
at
0.05
ppm.

Background
Triflumizole
is
an
imidazole
fungicide
that
inhibits
ergosterol
biosynthesis
in
fungi.
The
petitioner
is
proposing
Procure
®
50WS
(
EPA
Reg
No.
400­
431),
a
50%
wettable­
powder
(
WP)
formulation
of
triflumizole,
for
use
on
filberts.

Permanent
tolerances
are
established
under
40
CFR
§
180.476(
a)
for
the
combined
residues
of
triflumizole
and
its
metabolites
containing
the
4­
chloro­
2­
trifluoromethylaniline
moiety,
calculated
as
parent
compound,
in/
on
apples,
grapes,
pears,
strawberries,
cherries
and
cucurbits.
In
addition,
Page
2
of
8
permanent
tolerances
for
livestock
commodities
have
been
established
under
40
CFR
§
180.476(
b)
for
the
combined
residues
of
triflumizole,
the
metabolite
4­
chloro­
2­
hydroxy­
6­
trifluoromethylaniline
sulfate,
and
other
metabolites
containing
the
4­
chloro­
2­
trifluoromethylaniline
moiety,
calculated
as
parent
compound,
in/
on
milk;
eggs;
meat,
fat,
and
meat
byproducts
(
mbyp)
of
cattle,
goats,
hogs,
horses,
and
sheep;
and
in/
on
meat,
and
mbyp
of
poultry.

Residue
Chemistry
Deficiencies
°
None.

HED
Conclusions/
Recommendations
The
current
residue
chemistry
database
supports
the
establishment
of
the
following
permanent
tolerance
for
residues
of
triflumizole,
[
1­((
4­
chloro­
2­(
trifluoromethyl)
phenyl)
imino­
2­
propoxyethyl]­
1H­
imidazole,
and
its
metabolites
containing
the
4­
chloro­
2­
trifluoromethylaniline
moiety,
calculated
as
the
parent
compound:
filbert
at
0.05
ppm.

Note:
The
most
recent
human­
health
risk
assessment
(
Memo,
J.
Tyler
et
al.,
1/
28/
05;
D306463)
and
dietary
exposure
assessment
(
Memo,
J.
Tyler,
1/
28/
05;
D312453)
were
performed
by
HED
in
conjunction
with
a
Section
18
Emergency
Exemption
request
for
the
use
of
triflumizole
on
several
commodities.
In
that
assessment,
a
tolerance
of
0.05
ppm
was
used
for
filberts.
Therefore,
the
aforementioned
recent
human­
health
risk
assessment
is
adequately
protective
of
any
potential
for
triflumizole
residues
in/
on
filberts
as
a
result
of
the
current
action.
A
new
human­
health
risk
assessment
is
not
needed
at
this
time.

Detailed
Considerations
860.1200
Directions
for
Use
The
petitioner
is
proposing
use
of
triflumizole
on
filberts
to
control
eastern
blight.
A
specimen
label
was
provided
for
Procure
®
50WS
(
EPA
Reg.
No.
400­
431),
a
50%
WP
formulation.

Table
1.
Summary
of
Directions
for
Registered
and
Proposed
Uses
of
Triflumizole
Applic.
Type
RTI
1
(
days)
Formulation
(
EPA
Reg.
No.)
Applic.
Rate
(
lb
ai/
A)
Max.
No.
Applic.
per
Season
Max.
Seasonal
Applic.
Rate
(
lb
ai/
A)
PHI
2
(
days)
Use
Directions
and
Limitations
Foliar
10­
14
Procure
®
50WS
(
EPA
Reg
No.
400­
431)
0.125­
0.25
4
1.0
Not
Specified
Applications
are
made
by
ground
or
air
using
minimum
spray
volumes
of
100
and
15
gallons/
A,
respectively.
The
highest
label
rate
should
be
used
for
air
applications.
Apply
in
sufficient
spray
volume
to
ensure
coverage.
Tank
mixing
the
lowest
labeled
rate
of
a
spray
surfactant
my
improve
coverage.
Ground
application
is
preferred.
Applications
should
be
made
at
budbreak
as
a
preventative
spray.

1
RTI
=
Retreatment
Interval.
2
PHI
=
Preharvest
Interval.
3
NA
=
Not
Applicable.
Page
3
of
8
HED
Conclusions:
The
use
directions
on
the
submitted
label
do
not
match
the
use
pattern
employed
in
the
submitted
crop
field
trials,
in
which
treated
plots
received
a
total
of
six
foliar
applications
of
triflumizole
at
~
0.75
lb
ai/
A/
application,
for
a
total
application
rate
of
~
4.5
lb.
ai/
A
(
4.5x
the
proposed
seasonal
application
rate).
Applications
were
made
at
retreatment
intervals
(
RTIs)
of
14­
16
days
(
except
for
110­
111
days
between
the
fourth
and
fifth
application),
and
samples
were
collected
18­
19
days
following
the
last
application.
However,
as
the
combined
residues
of
triflumizole
and
it
metabolite
FA­
1­
1
were
<
0.05
ppm
[<
limit
of
quantitation
(
LOQ)]
in/
on
filberts
samples,
the
submitted
filbert
field
trial
data
are
adequate
and
support
the
proposed
tolerance
of
0.05
ppm
for
residues
of
triflumizole
on
filbert.

In
addition,
the
proposed
label
did
not
include
a
PHI
for
filberts.
The
available
residue
data
support
a
18­
day
PHI.
Therefore,
the
label
should
be
amended
to
include
a
PHI
of
18
days
for
filberts.

860.1300
Nature
of
the
Residue
­
Plants
and
Livestock
The
nature
of
the
residue
in
fruit
is
adequately
understood
based
on
acceptable
metabolism
data
on
apples,
cucumbers,
grapes,
and
pears.
The
results
of
metabolism
studies
were
extensively
discussed
in
connection
with
PP#
5G3232
(
Memo,
N.
Dodd,
7/
3/
85).
HED
concluded
that
the
residues
of
concern
in/
on
apples,
pears,
cucumbers
and
grapes
include
the
parent
compound,
triflumizole
and
its
metabolites
(
free
and
conjugates)
containing
the
4­
chloro­
2­
trifluormethyaniline
moiety
(
calculated
as
triflumizole).
In
a
meeting
on
2/
26/
02,
HED
MARC
concluded
that
there
was
no
need
to
revisit
the
residues
of
concern
in
primary
crops
(
Memo,
J.
Tyler,
3/
13/
02;
D280869).
The
MARC
concurred
with
the
current
tolerance
expression
for
plants
as
stated
in
40
CFR
§
180.476.

There
are
no
livestock
feed
items
associated
with
the
proposed
uses;
therefore,
a
discussion
of
potential
transfer
of
secondary
residues
to
livestock
commodities
is
not
relevant
to
this
petition.

860.1340
Residue
Analytical
Methods
The
method
used
in
the
crop
field
trial
is
suitable
for
data
gathering
purposes.
Samples
of
filberts
were
analyzed
using
a
gas
chromatography/
mass
selective
detector
(
GC/
MSD)
method
entitled
Morse
Method
Meth­
115
Rev
#
2,
with
Morse
Labs,
Inc.
Modifications
10­
31000.
Morse
Method
METH­
115,
Revision
#
2
converts
residues
of
triflumizole
and
its
aniline­
containing
metabolites
to
FA­
1­
1
which
is
then
quantified
as
triflumizole
equivalents.
The
validated
LOQ
for
both
triflumizole
and
FA­
1­
1
was
0.05
ppm
in
filberts.
A
similar
GC/
nitrogen­
phosphorous
detector
(
NPD)
method
has
been
deemed
acceptable
as
a
tolerance
enforcement
method
in
conjunction
with
a
petition
for
use
on
apples,
grapes,
and
pears,
and
has
been
forwarded
to
the
Food
and
Drug
Administration
(
FDA)
for
inclusion
in
the
Pesticide
Analytical
Manual
(
PAM),
Volume
II
as
Method
I
(
G.
Kramer,
12/
16/
94).
For
the
purposes
of
this
petition,
HED
concludes
that
the
current
enforcement
method
is
appropriate
for
enforcement
of
the
tolerance
associated
with
this
petition.

There
are
no
livestock
feed
items
associated
with
the
proposed
uses;
therefore,
data
collection
and
tolerance
enforcement
methods
for
livestock
commodities
are
not
required
for
the
Page
4
of
8
establishment
of
a
tolerance
for
triflumizole
residues
in/
on
the
proposes
uses.
However,
adequate
methods
are
available
for
determining
residues
of
triflumizole,
its
sulfate
metabolite,
and
other
metabolites
containing
the
4­
chloro­
2­
trifluromethylaniline
moiety
in
livestock
commodities.
These
methods
are
listed
as
Methods
II
and
III
in
PAM­
II.

860.1360
Multiresidue
Method
(
MRM)

FDA
PESTDATA
database
(
PAM
Volume
I,
Appendix
I,
3rd
edition,
1994)
indicates
that
triflumizole
is
completely
recovered
(>
80%)
by
Multiresidue
Protocol
D
(
PAM
I
Sections
232.4).

860.1380
Storage
Stability
The
storage
stability
data
submitted
in
conjunction
with
the
magnitude
of
the
residue
study
are
adequate.
The
maximum
storage
interval
of
filbert
samples,
from
harvest
to
analysis,
was
108
days
(~
3.6
months).
The
storage
stability
of
triflumizole
residues
in
filberts
was
evaluated
for
a
storage
period
of
97
days
(~
3.2
months),
in
which
corrected
recoveries
of
triflumizole
and
it
metabolite
FA­
1­
1
were
120
±
31%
and
97
±
23%,
respectively.
In
addition,
previouslysubmitted
storage
stability
data
indicate
that
triflumizole
is
stable
for
up
to
10
months
in
frozen
cucurbits
vegetables
(
MRID
449713­
01
thru
­
03;
Memo,
J.
Tyler,
3/
11/
02;
D271003)
and
strawberries
(
MRID
45375406;
J.
Tyler,
3/
11/
02;
D274589)
and
up
to
­

12
months
in
frozen
cherries
(
MRID
44438401;
Memo,
J.
Tyler,
4/
30/
01;
D242429)
and
apples
and
grapes
(
MRID
41131203;
Memo,
S.
Malak,
1/
25/
90,
DEB#
s
5479
&
5480).

860.1480
Meat,
Milk,
Poultry,
and
Eggs
As
there
are
no
livestock
feed
items
associated
with
the
proposed
uses,
data
on
residues
of
triflumizole
in
livestock
tissues,
milk
and
eggs
are
not
required
to
support
the
current
action.

860.1500
Crop
Field
Trials
45810201.
der.
wpd
IR­
4
has
submitted
a
magnitude
of
the
residue
study
reflecting
treatment
of
filberts
with
triflumizole.
Three
filbert
trials
were
conducted
in
Region
12
[
Oregon
(
OR)].
Each
of
the
three
field
trials
consisted
of
one
untreated
control
plot
and
one
treated
plot.
The
treated
plots
received
a
total
of
six
foliar
applications
of
the
test
substance
(
Procure
®
50WS)
at
~
0.75
lb
ai/
A/
application,
for
a
total
application
rate
of
~
4.5
lb.
ai/
A
(
4.5x
the
proposed
seasonal
application
rate).
Applications
were
made
at
RTIs
of
14­
16
days
(
except
for
110­
111
days
between
the
fourth
and
fifth
application),
and
samples
were
collected
18­
19
days
following
the
last
application.
The
combined
residues
of
triflumizole
and
metabolite
FA­
1­
1
were
<
0.05
ppm
(<
LOQ)
in/
on
all
six
filbert
samples.
Page
5
of
8
Table
2.
Summary
of
Residue
Data
from
Crop
Field
Trials
with
Imidacloprid.

Commodity
Total
Applic.
Rate
(
lb
ai/
A)
PHI
(
days)
1
Residue
Levels
(
ppm)

n
Min.
Max.
HAFT1
Median
Mean
Std.
Dev.

Filbert
nutmeat
4.54­
4.63
18­
19
6
<
0.05
<
0.05
<
0.05
<
0.05
<
0.05
­

1
PHI
=
preharvest
interval.
2
HAFT
=
Highest­
Average
Field
Trial.

HED
Conclusions:
Geographic
representation
and
the
number
of
filbert
trials
conducted
are
adequate
and
match
current
guidelines
(
OPPTS.
GLN
860.1500)
for
a
tolerance
on
filberts.
The
petitioner
provided
residue
data
from
a
total
of
3
trials
in
Region
12.
According
to
Table
1
of
OPPTS
860.1500,
registrants
have
the
option
of
doing
3
trials
with
two
treated
samples
(
1x
rate)
per
trial
or
2
trials
with
four
treated
samples
(
two
at
1x
;
two
at
2x
rate)
per
trial.
No
suggested
distribution
of
field
trials
is
available;
however,
according
to
Table
6
of
OPPTS
860.1500,
100%
of
the
filbert
production
in
the
U.
S.
occurs
in
Region
12.

The
combined
residues
of
triflumizole
and
it
metabolite
FA­
1­
1
were
<
0.05
ppm
(<
LOQ)
in/
on
filberts
samples
following
six
applications
of
triflumizole
(
formulated
as
Procure
®
50WS)
at
~
0.75
lb
ai/
A/
application,
for
a
total
application
rate
of
4.5
lb
ai/
A
(
4.5x
the
proposed
seasonal
use
rate;
PHI
of
18­
19
days).
Although
the
submitted
filbert
field
trials
were
performed
at
4.5x
the
proposed
application
rate,
the
residues
were
<
LOQ
in
all
samples.
Therefore,
the
submitted
filbert
field
trial
data
are
adequate
and
support
the
proposed
tolerance
of
0.05
ppm
for
residues
of
triflumizole
on
filbert.
An
acceptable
method
was
used
for
quantitation
of
residues
in/
on
filberts.

860.1520
Processed
Food
and
Feed
This
guideline
is
not
applicable
as
there
are
no
regulated
processed
commodities
associated
with
filberts.

860.1850/
1900
Confined/
Field
Accumulation
in
Rotational
Crops
This
guideline
is
not
applicable
as
filberts
are
not
considered
to
be
a
rotated
crop.

860.1550
Proposed
Tolerances
The
residue
chemistry
database
supports
the
establishment
of
the
permanent
tolerances
for
the
combined
residues
of
residues
of
triflumizole,
[
1­((
4­
chloro­
2­(
trifluoromethyl)
phenyl)
imino­
2­
propoxyethyl]­
1H­
imidazole,
and
its
metabolites
containing
the
4­
chloro­
2­
trifluoromethylaniline
moiety,
calculated
as
the
parent
compound,
in/
on
the
raw
agricultural
commodity
(
RAC)
listed
in
Table
3.
Page
6
of
8
Table
3.
Tolerance
Summary
for
Triflumizole
Commodity
Proposed
Tolerance
(
ppm)
Recommended
Tolerance
(
ppm)
Comments
(
correct
commodity
definition)

Filbert
0.05
0.05
­

The
International
Residue
Limit
Status
(
IRLS)
Sheet
is
attached
as
Attachment
1.
There
are
no
established
Codex,
Canadian
or
Mexican
maximum
residue
limits
(
MRLs)
for
triflumizole
in/
on
filbert.
Therefore,
harmonization
is
not
an
issue
at
this
time.

cc:
J.
Tyler
(
RAB1)
RDI:
PV
Shah
(
5/
18/
05),
G.
Kramer
(
5/
11/
05);
RAB1
Chemists
(
5/
11/
05)
J.
Tyler:
809B:
CM#
2:
(
703)
305­
5564:
7509C:
RAB1
ATTACHMENT
1
INTERNATIONAL
RESIDUE
LIMIT
STATUS
Chemical
Name:
[
1­((
4­
chloro­
2­
(
trifluoromethyl)
phenyl
)
imino­
2­
propoxyethyl]­
1Himidazole
Common
Name:
Triflumizole
x
Proposed
tolerance
9
Reevaluated
tolerance
9
Other
Date:
4/
12/
05
Codex
Status
(
Maximum
Residue
Limits)
U.
S.
Tolerances
X
No
Codex
proposal
step
6
or
above
9
No
Codex
proposal
step
6
or
above
for
the
crops
requested
Petition
Number:
DP
Barcode:
312293
Other
Identifier:

Residue
definition
(
step
8/
CXL):
N/
A
Reviewer/
Branch:
J.
Tyler/
RAB1
Residue
definition:
triflumizole,
[
1­((
4­
chloro­
2­
(
trifluoromethyl)
phenyl)
imino­
2­
propoxyethyl]­
1H­
imidazole,
and
its
metabolites
containing
the
4­
chloro­
2­
trifluoromethylaniline
moiety,
calculated
as
the
parent
compound
Crop
(
s)
MRL
(
mg/
kg)
Crop(
s)
Tolerance
(
ppm)

Filbert
0.05
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:
1­[
1­[[
4­
chloro­
2­
(
trifluoromethyl)
phenyl]
imino]­
2­
propoxyethyl]­
1Himidazole,
including
metabolites
containing
the
4­
chloro­
2­
trifluoromethylaniline
moiety,
expressed
as
triflumizole
Residue
definition:

triflumizole
Crop(
s)
MRL
(
mg/
kg)
Crop(
s)
MRL
(
mg/
kg)

Notes/
Special
Instructions:
S.
Funk,
04/
12/
2005.
Page
8
of
8
Rev.
1998