UNITED
STATES
ENVIRONMENTAL
PROTECTION
AGENCY
WASHINGTON,
D.
C.
20460
OFFICE
OF
PREVENTION,
PESTICIDES,
AND
TOXIC
SUBSTANCES
MEMORANDUM
Date:
November
2,
2005
Subject:
Bitertanol.
Summary
of
Analytical
Chemistry
and
Residue
Data
for
the
Tolerance
Reassessment
Eligibility
Decision
(
TRED)
Document.

DP
Barcode:
D302882
PC
Code:
117801
40
CFR
§
:
180.457
Chemical
Class:
Azole
From:
Samuel
Ary,
Chemist
Reregistration
Branch
II
Health
Effects
Division
(
7509C)

Through:
Sherrie
L.
Kinard,
Chemist
Reregistration
Branch
II
Health
Effects
Division
(
7509C)

Chemistry
Science
Advisory
Council
Health
Effects
Division
(
7509C)

Alan
Nielsen,
Branch
Senior
Scientist
Reregistration
Branch
II
Health
Effects
Division
(
7509C)

To:
Christina
Jarvis,
Risk
Assessor
Reregistration
Branch
II
Health
Effects
Division
(
7509C)

Rosanna
G.
Louie,
Chemical
Review
Manager
Reregistration
Branch
III
Special
Review
and
Reregistration
Division
(
7508C)

This
summary
of
analytical
chemistry
and
residue
data
document
was
originally
prepared
under
contract
by
Versar,
Inc.
(
6850
Versar
Center,
Springfield,
VA
22151;
submitted
August
16,
2004).
The
summary
document
has
been
reviewed
by
the
Health
Effects
Division
(
HED)
and
revised
to
reflect
current
Office
of
Pesticide
Program
(
OPP)
policies.
Bitertanol
Summary
Analytical
Chemistry
and
Residue
Data
DP
Barcode:
302882
2
of
17
Executive
Summary
Bitertanol,
$­([
1,1
'­
biphenyl]­
4­
yloxy)­"­(
1,1­
dimethylethyl)­
1H­
1,2,4­
triazole­
1­
ethanol,
is
a
fungicide
used
for
the
control
of
black
sigatoka,
a
fungal
disease
that
destroys
the
leaf
tissue
of
the
banana
plant.
Bitertanol
is
formulated
as
an
emulsifiable
concentrate
(
EC)
or
suspension
concentrate
(
SC)
and
may
be
applied
as
a
foliar
spray
by
airplane,
tractor
driven
equipment,
or
knapsack
sprayer.
Bitertanol
end­
use
products
are
marketed
under
the
trade
name
Baycor
®
.
The
active
ingredient
constitutes
30%
for
the
EC
formulation
and
50%
for
the
SC
formulation.
Applications
are
as
needed
and
based
on
the
speed
of
leaf
emergence
with
a
maximum
of
8
applications
during
the
development
period
of
a
fruit
bunch.
The
rate
per
application
is
0.13
lb
ai/
A
for
a
maximum
seasonal
application
rate
of
1.1
lb
ai/
A.
It
is
intended
for
use
on
bagged
bananas
only.
There
are
no
U.
S.
registrations
for
bitertanol.

A
tolerance
has
been
established
under
40
CFR
§
180.457
for
the
residues
of
bitertanol
in/
on
bananas
at
0.20
ppm.
This
tolerance
is
an
import
tolerance
since
bitertanol
is
not
registered
for
use
in
the
U.
S.
The
Codex
Alimentarius
Commission
(
Codex)
has
established
a
maximum
residue
limit
(
MRL)
for
bitertanol
residues
in/
on
bananas
at
0.5
mg/
kg.
Additionally,
the
Codex
MRL
for
bitertanol
is
expressed
in
terms
of
residues
of
bitertanol
only,
as
is
the
U.
S.
tolerance
expression.
It
is
the
Agency's
policy
to
harmonize
its
tolerances
with
the
levels
established
by
Codex
provided
that
the
Agency
has
sufficient
information
to
make
a
determination
that
the
Codex
MRLs
will
be
protective
of
the
health
of
the
U.
S.
public
and
meet
FFDCA
standards.
The
established
tolerance
should
be
reassessed
to
0.50
ppm
to
harmonize
with
Codex
as
the
dietary
exposure
and
risk
are
not
of
concern
(
S.
Ary,
D302880,
11/
2/
2005).

The
nature
of
residues
in
plants
is
adequately
understood
based
on
acceptable
plant
metabolism
studies
in
apples
and
peanuts
conducted
with
bitertanol
labeled
in
the
biphenyl
ring
system
and
additional
studies
submitted
recently
in
apples,
cotton,
and
tomatoes
conducted
with
bitertanol
labeled
in
the
traizole
ring
system.
The
recently
submitted
studies
are
currently
under
review
by
the
Agency,
however
it
is
noted
that
after
initial
review
of
the
newly
submitted
studies,
the
data
support
the
conclusions
drawn
from
the
two
previous
submissions.
The
residues
identified
in
these
studies
consisted
primarily
of
the
parent
compound
with
traces
of
the
metabolites
bitertanol
ketone
and
4­
hydroxybiphenol.
Although
no
metabolism
studies
for
bananas
are
available,
HED
has
concluded
that
the
nature
of
residues
in
bananas
is
likely
similar
to
that
in
apples,
cotton,
peanuts,
and
tomatoes.
Therefore,
HED
has
determined
that
the
bitertanol
residues
of
concern
in/
on
bananas
for
tolerance
expression
and
for
risk
assessment
are
bitertanol.

Additionally,
the
Agency
does
have
concern
about
the
potential
toxicity
of
1,2,4­
triazole
and
two
conjugates,
triazole
alanine
and
triazole
acetic
acid,
which
are
metabolites
common
to
most
of
the
triazole
fungicides.
To
support
the
extension
of
existing
and
granting
of
new
parent
triazolederivative
fungicide
tolerances,
the
Agency
will
be
conducting
a
human­
health
assessment
for
aggregate
exposure
to
1,2,4­
triazole.

An
analytical
method
for
analysis
of
residues
of
bitertanol
has
been
submitted
and
found
acceptable
for
data
collection
purposes.
The
submitted
method
is
a
modification
of
Mobay
Chemical
Corporation's
Method
54166
for
the
analysis
of
bitertanol
in
apples.
Analysis
is
by
gas
chromatography
using
a
nitrogen­
phosphorus
flame
ionization
detector.
The
limit
of
detection
is
Bitertanol
Summary
Analytical
Chemistry
and
Residue
Data
DP
Barcode:
302882
3
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17
0.01
ppm.
A
method
trial
was
successfully
performed
on
banana
pulp
and
peels
at
fortification
levels
of
0.1
ppm
and
0.2
ppm.
Recoveries
ranged
from
78
to
88%
for
pulp
samples,
and
from
70
to
98%
for
peel
samples.
The
method
was
approved
by
the
Agency
for
the
enforcement
of
tolerance
in/
on
bananas
and
the
results
were
forwarded
to
FDA
for
inclusion
in
the
Pesticide
Analytical
Manual
(
PAM)
Volume
II.

The
FDA
PESTDATA
database
dated
11/
2001
(
PAM
Volume
I,
Appendix
I)
indicates
that
bitertanol
was
completely
recovered
using
Multiresidue
Method
Section
302
(
Protocol
D).

Storage
stability
data
for
bitertanol
in/
on
bananas
have
not
been
submitted
by
the
registrant,
therefore,
storage
stability
data
are
required
As
indicated
in
the
tolerance
petition,
bitertanol
was
originally
marketed
for
use
on
bananas
in
Costa
Rica
and
Honduras,
but
has
expanded
to
include
Ecuador,
Guatemala,
Honduras,
Mexico,
Nicaragua,
Peru,
Venezuela,
Dominican
Republic,
and
Panama.
Residue
data
from
trials
conducted
in
Costa
Rica
and
Honduras
have
been
submitted
and
reviewed
by
the
Agency.
Bitertanol
was
applied
to
both
bagged
and
unbagged
bunches
of
green
and
ripe
bananas
at
a
rate
of
0.26
lb
ai/
A/
application
(
2x
the
current
rate
per
application),
the
maximum
rate
per
application
indicated
on
the
product
label
at
that
time.
Samples
of
peel,
pulp
and
whole
fruit
were
collected
3
days
after
the
last
of
9
treatments
and
0
days
after
the
last
of
12
treatments.
Washed
and
unwashed
samples
were
analyzed
for
bitertanol
by
Method
54166,
with
modifications.
The
number
of
trials,
the
location
of
the
trials
within
Costa
Rica
and
Honduras,
and
the
formulation
type
were
not
specified.
No
data
were
provided
on
how
long
the
samples
were
stored
prior
to
analysis.
Residues
found
in
samples
of
whole
fruit
from
unbagged
and
bagged
bunches
of
ripe
and
green
bananas
were
all
below
the
recommended
tolerance
level
of
0.5
ppm.
The
residue
data
are
deemed
adequate
to
support
a
tolerance
of
0.5
ppm
in/
on
bananas.

The
SC
formulation
will
be
supported
with
additional
field
trials
that
are
currently
being
conducted
by
the
registrant.
The
studies
are
planned
for
completion
in
2006.

Regulatory
Recommendations
and
Residue
Chemistry
Deficiencies
°
Revise
tolerance
to
0.50
ppm
to
harmonize
with
Codex.

°
Storage
stability
data
are
required
to
determine
the
stability
of
residues
in
bananas
during
cold
storage.
No
data
were
provided
on
how
long
the
banana
samples
from
submitted
field
trial
studies
were
stored
prior
to
analysis.

°
Field
trial
data
for
the
SC
formulation
are
required.

°
Additional
data
are
required
in
order
for
the
submitted
field
trials
conducted
in
Costa
Rica
and
Honduras
to
be
acceptable.
The
number
of
trials,
location
of
the
trials
within
the
countries,
and
the
formulation
type
used.
Bitertanol
Summary
Analytical
Chemistry
and
Residue
Data
DP
Barcode:
302882
4
of
17
O
N
N
N
OH
Background
The
chemical
structure
and
nomenclature
of
bitertanol
are
listed
in
Table
1
and
the
chemical
names
and
structures
of
the
metabolites
of
bitertanol
are
presented
in
Table
3.
Table
2
presents
the
physicochemical
properties
of
bitertanol.

Table
1.
Test
Compound
Nomenclature.

Chemical
structure
Common
name
Bitertanol
Trade
name
Baycor
®

Company
experimental
name
KWG
0599
Molecular
formula
C20H23N3O2
IUPAC
name
1­(
biphenyl­
4­
yloxy)­
3,3­
dimethyl­
1­(
1H­
1,2,4­
triazol­
1­
yl)
butan­
2­
ol
CAS
name
$­(
1,1'­
biphenyl)­
4­
yloxy­"­(
1,1­
dimethylethyl)­
1H­
1,2,4­
triazole­
1­
ethanol
CAS
number
55179­
31­
2
PC
Code
117801
Table
2.
Physicochemical
Properties
of
the
Technical
Grade
Test
Compound.

Parameter
Value
Reference
Molecular
weight
337.42
g/
mol
MRID
46655901
Melting
point/
range
145­
155
°
C
MRID
46655901
pH
Not
available
Density
1.16
g/
mL
at
20
°
C
MRID
46655901
Water
solubility
1.1
mg/
L
at
20
°
C
for
isomer
A
MRID
46655901
2.7
mg/
L
at
20
°
C
for
isomer
B
Solvent
solubility
(
temperature
not
specified)
1­
5
g/
100g
of
propan­
2­
ol,
1­
5
g/
100g
of
toluene,
5­
10
g/
100g
of
cyclohexane,
10­
20
g/
100g
of
methylene
chloride
Stable
in
aqueous
acid
and
alkaline
solutions.
Merck
Index
12th
Edition
Vapor
pressure
10­
5
mBar
at
20
°
C
Merck
Index
12th
Edition
Dissociation
constant
(
pKa)
None
MRID
46655901
Octanol/
water
partition
coefficient
Log(
KOW)
K
OW
log
P
=
4.04
at
20
°
C
for
isomer
A
MRID
46655901
K
OW
log
P
=
4.10
at
20
°
C
for
isomer
B
UV/
visible
absorption
spectrum
Peak
maximum
at
255
nm
MRID
46655901
Bitertanol
Summary
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Data
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O
N
N
N
O
O
H
Table
3.
Chemical
Names
and
Structures
of
Metabolites
of
Bitertanol.

Common
Name
Chemical
Name
Structure
bitertanol
ketone
1­[(
1,1­
biphenyl)­
4­
yloxy]­
3,3­
dimethyl­
1­(
1H­
1,2,4­
triazole­
1­
yl)­
2­
butanone
p­
hydroxybiphenyl
4­
hydroxybiphenyl
Summary
of
Science
Findings
860.1200
Directions
for
Use
Product
List
There
are
no
U.
S.
registrations
for
bitertanol.
An
import
tolerance
for
residues
of
bitertanol
in/
on
bananas
was
established
through
a
petition
(
PP#
2E2756)
submitted
by
Mobay
Chemical
Corporation.
As
indicated
in
the
tolerance
petition,
bitertanol
was
originally
marketed
for
use
on
bananas
in
Costa
Rica
and
Honduras,
but
has
expanded
to
include
Ecuador,
Guatemala,
Honduras,
Mexico,
Nicaragua,
Peru,
Venezuela,
Dominican
Republic,
and
Panama.
There
are
two
Bayer
CropScience
end­
use
products
containing
the
active
ingredient
bitertanol
as
indicated
in
Table
4.
The
variation
in
product
names
reflect
different
product
naming
requirements
depending
on
which
country
each
product
is
registered
in.

Table
4.
Bitertanol
End­
Use
Products
(
EPs)
with
Food/
Feed
Uses.

EPA
Reg.
No.
1
Formulation2
Label
Acceptance
Date1
Registrant
Product
Name
Commodity
N/
A
=
not
applicable
30%
EC
N/
A
Bayer
CropScience
Baycor
®
300
EC,
Baycor
®
30
EC,
Baycor
®
300
DC,
and
Baycor
®
300
CE
Banana
N/
A
50%
SC
N/
A
Bayer
CropScience
Baycor
®
500
EC
and
Baycor
®
50
SC
Banana
1.
There
are
no
U.
S.
registrations
for
bitertanol.
2.
EC
=
emulsifiable
concentrate
and
SC
=
soluble
concentrate.

Bitertanol
is
formulated
as
an
emulsifiable
concentrate
(
EC)
or
suspension
concentrate
(
SC)
and
may
be
applied
as
a
foliar
spray
by
airplane,
tractor
driven
equipment,
or
knapsack
sprayer.
The
active
ingredient
constitutes
30%
for
the
EC
formulation
and
50%
for
the
SC
formulation.
Applications
are
as
needed
and
based
on
the
speed
of
leaf
emergence
with
a
maximum
of
8
applications
during
the
development
period
of
a
fruit
bunch.
The
rate
per
application
is
0.13
lb
ai/
A
for
a
maximum
seasonal
application
rate
of
1.06
lb
ai/
A.
It
is
intended
for
use
on
bagged
bananas
only,
however,
application
to
unbagged
bananas
may
occur.
The
current
labels
do
not
Bitertanol
Summary
Analytical
Chemistry
and
Residue
Data
DP
Barcode:
302882
6
of
17
restrict
application
to
bagged
bananas
and
does
not
specify
any
pre­
harvest
interval
(
PHI)
requirements.

There
are
no
U.
S.
registrations
for
bitertanol.
An
import
tolerance
for
residues
of
bitertanol
in/
on
bananas
was
established
through
a
petition
(
PP#
2E2756)
submitted
by
Mobay
Chemical
Corporation.
As
indicated
in
the
tolerance
petition,
bitertanol
was
originally
marketed
for
use
on
bananas
in
Costa
Rica
and
Honduras,
but
has
expanded
to
include
Ecuador,
Guatemala,
Honduras,
Mexico,
Nicaragua,
Peru,
Venezuela,
Dominican
Republic,
and
Panama.

Bitertanol
is
formulated
as
an
EC
that
contains
30%
active
ingredient
(
Baycor
®
300
EC,
Baycor
®

30
EC,
Baycor
®
300
DC,
and
Baycor
®
300CE)
or
SC
that
contains
50%
active
ingredient
(
Baycor
®
500
EC
and
Baycor
®
50SC).

Use
Patterns
A
summary
of
the
direction
for
the
use
of
bitertanol
is
presented
in
Table
5.
Based
on
label
information
provided
by
the
petitioner,
bitertanol
can
be
applied
as
needed
based
on
the
speed
of
leaf
emergence
with
a
maximum
of
8
applications
during
the
development
period
of
a
fruit
bunch.
The
maximum
rate
per
application
is
0.133
lb
ai/
A
for
a
total
seasonal
application
rate
of
1.064
lb
ai/
A.
Bitertanol
can
be
applied
as
a
foliar
spray
by
air
in
a
minimum
of
2
gallons
of
water
per
acre.
It
is
intended
for
use
on
bagged
bananas
only,
however,
application
to
unbagged
bananas
may
occur.
The
current
labels
do
not
restrict
application
to
bagged
bananas
and
does
not
specify
any
PHI
requirements.

Table
5.
Summary
of
Directions
for
Use
of
Bitertanol.

Applic.
Timing,
Type,
and
Equip.
Formulation
Applic.
Rate
(
lb
ai/
A)
Max.
No.
Applic.
per
Season
Max.
Seasonal
Applic.
Rate
(
lb
ai/
A)
PHI
(
days)

Banana
Apply
as
needed
based
on
speed
of
leaf
emergence
during
fruit
development.
Minimum
retreatment
interval
of
7
days.
Apply
specified
dosage
as
a
foliar
spray
by
air,
tractor
driven
equipment,
or
knapsack
sprayer
in
a
minimum
of
2
gallons
of
water
per
acre.
Baycor
®

30%
EC
0.13
lb
ai/
A
8
1.06
lb
ai/
A
None
Apply
as
needed
based
on
speed
of
leaf
emergence
during
fruit
development.
Minimum
retreatment
interval
of
7
days.
Apply
specified
dosage
as
a
foliar
spray
by
air,
tractor
driven
equipment,
or
knapsack
sprayer
in
a
minimum
of
2
gallons
of
water
per
acre.
Baycor
®

50%
SC
0.13
lb
ai/
A
8
1.06
lb
ai/
A
None
A
tabular
summary
of
the
chemistry
science
assessments
is
presented
in
Table
6.
The
conclusions
listed
in
Table
6
regarding
the
reregistration
eligibility
of
bitertanol
food/
feed
uses
are
based
on
the
use
patterns
registered
by
the
basic
producer,
Bayer
CropScience.
Bitertanol
Summary
Analytical
Chemistry
and
Residue
Data
DP
Barcode:
302882
7
of
17
Table
6.
Residue
Chemistry
Science
Assessment
for
Reregistration
of
Bitertanol.

GLN
Data
Requirements
Current
Tolerances
(
ppm)
[
40
CFR]
Additional
Data
Needed?
MRID
Nos.

860.1200:
Directions
for
Use
N/
A
=
Not
Applicable
No
None
860.1300:
Nature
of
the
Residue
­
Plants
­
Bananas
N/
A
No
00025731,
00025734
860.1300:
Nature
of
the
Residue
­
Animals
N/
A
No
None
860.1340:
Residue
Analytical
Method
­
Plant
Commodities
N/
A
No
00025716,
00071187
­
Animal
Commodities
N/
A
No
None
860.1360:
Multiresidue
Method
N/
A
No1
None
860.1380:
Storage
Stability
Data
­
Plant
Commodities
N/
A
Yes2
None
­
Animal
Commodities
N/
A
No
None
860.1400:
Magnitude
of
the
Residue
­
Water,
Fish,
and
Irrigated
Crops
None
established
No
None
860.1460:
Magnitude
of
the
Residue
­
Food
Handling
None
established
No
None
860.1480:
Magnitude
of
the
Residue
­
Meat,
Milk,
Poultry,
and
Eggs
None
established
No
None
860.1500:
Crop
Field
Trials
­
Bananas
0.2
[
180.457]
Yes3
00071186,
00071188,
00114273
860.1520:
Processed
Food/
Feed
None
established
No
None
860.1650:
Submittal
of
Analytical
Reference
Standards
N/
A
Yes
None
860.1850:
Confined
Accumulation
in
Rotational
Crops
N/
A
No
None
860.1900:
Field
Accumulation
in
Rotational
Crops
None
established
No
None
1.
There
was
no
information
in
the
review
documents
regarding
submittal
of
data
for
FDA
multiresidue
methods
by
the
petitioner.
However,
the
FDA
PESTDATA
database
dated
11/
2001
(
PAM
Volume
I,
Appendix
I)
indicates
that
bitertanol
was
completely
recovered
using
Multiresidue
Method
Section
302
(
Protocol
D).
2.
Storage
stability
data
for
bitertanol
in/
on
bananas
have
not
been
submitted
by
the
registrant,
therefore,
storage
stability
data
are
required
(
HED
SOP
98.6).
No
information
on
the
stability
of
residues
in/
on
bananas
during
cold
storage
have
been
submitted.
Additionally,
no
data
were
provided
on
how
long
the
samples
were
stored
from
the
submitted
field
trial
studies
conducted
on
bananas
prior
to
analysis.
3.
Additional
data
are
required
in
order
for
the
submitted
field
trials
conducted
in
Costa
Rica
and
Honduras
to
be
acceptable.
The
number
of
trials,
location
of
the
trials
within
the
countries,
and
the
formulation
type
used.
New
field
trial
data
are
required
for
the
SC
formulation.
4.
Analytical
reference
standards
must
be
replenished
as
requested
by
the
Repository.

860.1300
Nature
of
the
Residue
­
Plants
The
nature
of
the
residue
in
plants
is
adequately
understood
based
on
acceptable
metabolism
Bitertanol
Summary
Analytical
Chemistry
and
Residue
Data
DP
Barcode:
302882
8
of
17
studies
on
apples
and
peanuts.
The
residues
consisted
primarily
of
the
parent
compound
with
traces
of
the
metabolites
bitertanol
ketone
and
4­
hydroxybiphenol.
The
Agency
concluded
that
the
residue
of
concern
is
the
parent
(
E.
Zager,
PP#
0G2311,
6/
30/
1980).

Apple
(
MRID
00025731)

Golden
Delicious
variety
apples
were
individually
syringe­
treated
to
run­
off
with
a
50%
wettable
powder
formulation
at
0.015
g
ai/
100
mL
(
2
oz
ai/
100
gallons
of
water)
of
14C­
bitertanol
labeled
uniformly
in
the
biphenyl
ring.
Sampling
(
6­
9
apples)
was
immediately
after
drying,
at
3,
7,
14,
23,
35,
42,
and
49
days.
The
apples
were
initially
subjected
to
several
methanol
rinses.
The
rinses
were
collected
and
analyzed.
The
apples
were
then
separated
into
peel
and
pulp,
portions
of
which
were
separately
homogenized
in
liquid
nitrogen.
Subsamples
of
each
portion
were
analyzed
for
total
activity.
Analysis
was
by
thin­
layer
chromatography
(
TLC)
using
radiochromatogram
scanning
and
autoradiography
techniques.

The
peel
contained
95%
of
the
total
recovered
radioactivity
even
after
49
days,
the
rest
being
in
the
pulp,
showing
that
little
migration
had
occurred.
Surface
residues
decreased
from
92%
at
day
0
to
43%
at
49
days
while
the
radioactivity
in
the
peel
organic
extract
increased
from
7%
to
44%
of
the
total.
Peel
solids
increased
to
12%
in
the
same
interval,
indicating
some
binding
had
occurred.

The
two
diasterioisomers
of
bitertanol
were
the
major
residues,
in
roughly
equal
proportions
throughout
the
49­
day
study.
The
level
of
the
two
combined
in
peel
and
pulp
ranged
from
98%
of
the
total
radioactivity
at
day
0
to
83%
at
49
days,
with
lower
surface
residues
and
greater
peel
uptake
by
the
end
of
that
time.
The
two
had
penetrated
the
pulp
by
day
7
from
which
time
residues
were
relatively
constant
at
about
3%
over
the
remaining
test
period.
Minor
metabolites
were
bitertanol
ketone
and
4­
hydroxybiphenyl,
together
never
exceeding
3%
of
the
total
radioactivity.
Both
of
the
metabolites
were
found
in
the
peel.
The
half­
life
of
bitertanol
in
this
experiment
was
estimated
at
approximately
150
days.

Peanut
(
MRID
00025734)

To
investigate
the
fate
of
bitertanol
in
peanuts,
bitertanol
labeled
in
the
biphenyl
ring
system
was
applied
to
peanut
plant
leaves;
to
1­
month
old
peanut
plants;
to
2­
month
old
peanut
plants
which
were
grown
to
maturity;
and
to
the
nutrient
solution
of
growing
peanut
plants.

Peanut
plant
leaflets
were
treated
with
14C­
bitertanol
and
samples
were
taken
at
3
and
14
days.
At
sampling
the
treated
leaves
were
rinsed
with
methanol
and
subsequently
extracted
with
dichloromethane
and
ACN.
After
3
days,
1.7%
of
the
applied
14C­
bitertanol
was
absorbed,
nearly
all
of
which
was
identified
as
bitertanol
by
TLC.
After
14
days,
3%
of
the
applied
14C­
bitertanol
was
found
in
the
extract
of
the
rinsed
leaves,
82%
of
which
was
bitertanol
and
14%
unidentified
polar
material.
The
remainder
of
the
applied
14C­
bitertanol
was
recovered
in
the
methanol
rinse
and
consisted
of
96%
bitertanol.
Total
recoveries
at
each
interval
were
100­
101%.
This
evidence
shows
that
foliar
application
result
in
poor
leaf
absorption
(
96%
unchanged
bitertanol
on
the
leaf
surface
after
14
days),
with
no
observable
volatility
losses.
Only
very
little
translocation
was
observed,
as
well
as
little
translocation
to
opposite
leaves.
Bitertanol
Summary
Analytical
Chemistry
and
Residue
Data
DP
Barcode:
302882
9
of
17
In
another
study,
14C­
bitertanol
uniformly
labelled
in
the
biphenyl
ring
was
sprayed
as
a
50%
WP
formulation
to
both
1­
month
and
2­
month
old
potted
peanut
plants
at
an
approximate
equivalent
field
rate
of
2.7
lbs
ai/
A.
Young
plants
were
sampled
at
12
and
28
days
after
treatment
and
the
older
plants
and
nuts
after
10
weeks.
In
the
1­
month
old
plants,
after
12
days
72%
and
after
28
days
61%
of
the
total
recovered
radioactivity
was
surface
residue,
the
remainder
were
extractable
residues
(
28%
at
12
days
and
39%
at
28
days).
In
the
2­
month
old
plants
the
distribution
was
46%
surface
and
50%
extractable.

In
the
1­
month
peanut
plants,
bitertanol
comprised
93%
and
86%
of
the
total
residue
at
12
days
and
28
days,
respectively.
Metabolite
R­
1,
apparently
a
glucoside
of
bitertanol,
constituted
2­
4%
of
the
total
residue.
Traces
(
0.6%)
of
the
metabolite
4­
hydroxybiphenyl
were
found
in
extracted
shoot
solids
of
the
28­
day
sample.
Little
movement
of
14C
was
observed
from
shoots
to
roots
of
the
peanut
plants.

In
the
2­
month
peanut
plants,
residues
in
the
foliage
were
16.8
ppm
bitertanol
equivalent,
with
75%
of
the
plant
residue
actually
identified
as
bitertanol.
Metabolite
R­
1
constituted
6%
of
the
residue
and
several
other
polar
metabolites
were
observed
with
none
constituting
more
than
1%
of
the
residue.
Residues
in
nut
meats
were
0.06
ppm
bitertanol
equivalent,
which
is
0.008%
of
the
total
plant
residue.

In
the
root
uptake
study,
young
peanut
plants
were
grown
for
7
days
in
a
nutrient
solution
fortified
with
biphenyl
labeled
14C­
bitertanol
at
1
ppm
followed
by
7
days
in
an
unfortified
nutrient
solution.
A
total
of
94%
of
the
administered
radioactivity
was
recovered
with
29%
in
the
roots,
15%
in
the
shoots,
40%
in
the
fortified
nutrient
solution,
and
11%
in
the
non­
fortified
solution.
Bitertanol
constituted
a
total
(
roots
and
shoots)
of
56%
of
the
absorbed
14C
while
the
metabolite
R­
1
(
glucoside
of
bitertanol)
accounted
for
16%.
Unextracted
shoot
solids
were
reacted
with
HI
which
released
9%
of
absorbed
14C
as
4­
hydroxybiphenyl.
Radioactivity
was
concentrated
in
the
veins,
but
distributed
throughout
the
plant.
No
translocation
to
new
growth
occurred
after
removal
of
the
fortified
solution.
Radioactivity
in
the
non­
fortified
solution
suggests
desorption
from
within
or
from
the
surface.

Additional
metabolism
studies
conducted
with
apples,
cotton,
and
tomatoes
have
been
submitted
and
are
under
review
by
the
Agency.
The
apple
(
Report
No.
94373,
3/
16/
1987)
and
cotton
(
Report
No.
94382,
4/
13/
1987)
metabolism
studies
were
conducted
with
14C­
bitertanol
labeled
in
the
triazole
ring.
The
tomato
(
Report
No.
M1731133­
9,
1/
15/
2003)
metabolism
studies
were
conducted
with
14C­
bitertanol
labeled
in
the
triazole
ring
and
in
the
phenyl
ring.

The
apple
metabolism
study
shows
that
bitertanol
is
slowly
metabolized
when
14C­
bitertanol
labeled
in
the
triazole
ring
is
applied
as
the
50%
WP
at
a
field
rate
of
2
oz
ai/
100
gallons
of
water
to
apple
fruit
(
less
than
5%
degradation
in
49
days).
All
samples
were
radioassayed
for
14C
content
by
liquid
scintillation
counting
(
LSC).
Quantitation
of
the
parent
and
metabolites
was
achieved
by
LSC
and
identified
by
TLC
and
high
performance
liquid
chromatography
(
HPLC).
There
was
very
little
penetration
of
bitertanol
into
the
fruit
pulp
throughout
the
49
day
sampling
interval.
The
majority
of
the
radiocarbon
(
91­
98%)
was
located
in
the
methanol
rinse
of
the
bag
and
fruit
at
every
time
interval.
From
2
to
9%
of
the
total
residues
were
found
to
be
associated
with
the
washed
peel
fraction,
i.
e.
not
removed
by
the
methanol
rinse.
No
more
than
1.5%
was
Bitertanol
Summary
Analytical
Chemistry
and
Residue
Data
DP
Barcode:
302882
10
of
17
found
associated
with
the
pulp
fraction
at
any
sampling
interval
with
no
trend
toward
increased
residues
over
time.
The
majority
of
organoextractable
residues
from
peel
and
pulp
were
identified
as
bitertanol
with
only
0.4­
2%
of
the
total
residues
being
identified
in
the
organosoluble
fractions.
Therefore,
96­
99%
of
the
total
recovered
residues
were
identified
as
intact
parent
bitertanol.
An
additional
0.1­
0.5%
of
the
total
residue
was
unidentified
as
water
soluble
components.

The
cotton
metabolism
study
was
conducted
with
14C­
bitertanol
labeled
in
the
triazole
ring
is
applied
as
the
50%
WP
at
a
field
rate
of
250
g
ai/
ha
in
a
volume
of
300
liters
to
cotton
plants
at
early
bloom
stage.
An
identical
second
treatment
was
made
14
days
following
second
treatment.
Samples
were
collected
following
the
second
treatment
and
at
7,
21,
35,
and
63
days
following
the
second
application.
Whole
plants
were
stored
frozen
pending
processing
and
analysis
for
0­
through
35­
day
intervals.
The
63­
day
interval
plants
(
mature
sample)
were
separated
into
foliage,
lint,
calyx,
seed,
and
hull
and
the
comments
also
stored
frozen
pending
processing
and
analysis.
All
samples
were
radioassayed
for
14C
content
by
liquid
scintillation
counting
(
LSC).
Quantitation
of
the
parent
and
metabolites
was
achieved
by
LSC
and
identified
by
TLC
and
HPLC.
In
mature
cotton
plants
63­
days
after
the
second
application
of
14C­
bitertanol
91%
of
the
total
recovered
radioactivity
was
associated
with
the
foliage
portion
of
the
plant;
6%
was
associated
with
the
calyx
fraction;
1.3%,
1%,
and
1%
were
associated
with
the
lint,
seed,
and
hull
respectively.
The
majority
of
the
recovered
radiocarbon
was
was
identified
as
intact
bitertanol,
amounting
to
a
total
of
79%
of
the
mature
harvest
interval
residue.
The
relative
concentration
of
bitertanol
isomers
remained
constant
throughout
the
study
period.
There
were
trace
amount
of
bitertanol
acid
and
two
metabolites
tentatively
identified
as
R­
1
and
R­
2
present
in
the
more
mature
time
intervals,
collectively
accounting
for
1.3%
and
0.3%
of
the
35­
day
and
63­
day
interval
samples
respectively.

The
metabolism
of
bitertanol
was
investigated
in
tomatoes
following
three
spray
applications
at
600
g
ai/
ha
for
a
total
of
1800
g
ai/
ha.
The
active
ingredient
was
14C­
bitertanol
labeled
in
the
triazole
and
was
formulated
as
a
SC.
The
first
application
was
performed
when
mainly
small
tomatoes
were
visible
and
a
few
flowers
were
still
open.
The
treatment
was
performed
when
most
of
the
fruits
had
reached
ca.
50%
of
the
final
size.
The
third
treatment
was
three
days
before
harvest,
when
ca.
30%
of
the
tomatoes
showed
the
typical
ripe
color.
All
samples
were
radioassayed
for
14C
content
by
LSC.
Quantitation
of
the
parent
and
metabolites
was
achieved
by
HPLC
and
identified
by
LC/
MS,
LC/
MS/
MS,
and
1H­
NMR
spectroscopy
experiments.
The
total
radioactive
residue
(
TRR)
in
tomatoes
amounted
for
to
7.76
mg/
kg,
expressed
as
parent
compound
equivalents.
Most
of
the
radioactivity
(
97%)
was
extracted
by
surface
wash
with
methanol.
After
homogenisation
of
the
tomatoes
and
extraction
with
acn/
water
the
residues
were
extracted
quantitatively
(
99%).
Unchanged
parent
compound
accounted
for
99%
of
the
TRR.
Two
minor
metabolites
<
0.1%
were
also
detected,
but
due
to
the
low
portion
of
the
TRR,
they
were
not
further
analyzed.
Judged
by
HPLC,
the
ratio
of
the
two
diasterioisomers
of
bitertanol
remained
nearly
unchanged
during
the
course
of
the
study.

The
other
tomato
study
was
conducted
in
the
same
way
as
noted
above,
however,
the
active
ingredient
was
14C­
bitertanol
labeled
in
the
phenyl
ring.
The
TRR
amounted
to
8.19
mg/
kg,
expressed
as
parent
compound
equivalents.
Most
of
the
radioactivity
(
96%)
was
extracted
by
surface
wash
with
methanol.
After
homogenisation
of
the
tomatoes
and
extraction
with
acn/
water
the
residues
were
extracted
quantitatively
(
99.6%).
Unchanged
parent
compound
accounted
for
99.5%
of
the
TRR
and
only
a
very
small
amount
was
detected
as
a
metabolite
(<
0.1%).
Judged
Bitertanol
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and
Residue
Data
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by
HPLC,
the
ratio
of
the
two
diasterioisomers
of
bitertanol
remained
nearly
unchanged
during
the
course
of
the
study.

In
the
plant
studies
bitertanol
penetration
from
surface
applications
was
minimal
and
there
was
little
volatility.
Residues
are
taken
up
by
roots,
although
translocation
into
the
plant
is
relatively
low.
There
are
some
measurable
but
not
major
differences
in
absorption,
translocation,
and
plant
metabolism
rates
of
the
two
diasterioisomeric
forms
of
bitertanol.
Bitertanol
is
by
far
the
main
plant
residue,
with
low
levels
of
bitertanol
ketone
and
4­
hydroxybiphenyl.

No
metabolism
studies
for
bananas
were
submitted.
However,
HED
has
concluded
that
the
nature
of
residues
in
bananas
is
likely
similar
to
that
in
apples,
cotton,
tomatoes,
and
peanuts.
Therefore,
HED
has
determined
that
the
bitertanol
residues
of
concern
in/
on
bananas
for
tolerance
expression
and
for
risk
assessment
are
bitertanol.

Additionally,
the
Agency
does
have
concern
about
the
potential
toxicity
of
1,2,4­
triazole
and
two
conjugates,
triazole
alanine
and
triazole
acetic
acid,
which
are
metabolites
common
to
most
of
the
triazole
fungicides.
To
support
the
extension
of
existing
and
granting
of
new
parent
triazolederivative
fungicide
tolerances,
the
Agency
will
be
conducting
a
human­
health
assessment
for
aggregate
exposure
to
1,2,4­
triazole.

860.1300
Nature
of
the
Residue
­
Livestock
Bitertanol
is
not
intended
for
application
to
livestock
exported
to
the
U.
S.
In
addition,
there
are
no
feedstuffs
associated
with
bananas.
Therefore,
no
residue
chemistry
data
are
required
under
this
guideline
topic.

860.1340
Residue
Analytical
Methods
An
analytical
method
for
analysis
of
residues
of
bitertanol
was
submitted
and
reviewed
in
PP#
2E2756.
The
submitted
method
is
a
modification
of
Mobay
Chemical
Corporation's
Method
54166
for
the
analysis
of
Baycor
®
in
apples.
The
modified
method
employs
different
gas
chromatography
(
GC)
parameters
and
column
packing
than
the
original
Method
54166.
The
modified
method
consists
of
extracting
the
residues
by
blending
successively
with
acetone
followed
by
dichloromethane.
The
samples
are
then
shaken
three
times
with
water
in
a
separatory
funnel.
The
water
is
discarded
and
the
organic
phase
is
collected,
evaporated,
and
cleaned
up
using
a
Florisil
column.
Analysis
is
by
GC
using
a
nitrogen/
phosphorus
flame
ionization
detector
(
NPD).
The
method
was
validated
by
the
Biological
and
Economic
Analysis
Division's
(
BEAD)
Analytical
Chemistry
Branch
(
ACB)
and
the
limit
of
quantitation
was
determined
at
0.1
ppm
(
A.
Burns,
PP#
2E2756,
3/
22/
1983).
The
method
trial
was
successfully
performed
on
banana
pulp
and
peels
at
fortification
levels
of
0.1
ppm
and
0.2
ppm.
Recoveries
ranged
from
78
to
88%
for
pulp
samples,
and
from
70
to
98%
for
peel
samples.
The
method
was
approved
by
the
Agency
for
the
enforcement
of
a
tolerance
in/
on
bananas
and
the
results
were
forwarded
to
FDA
for
inclusion
in
PAM
Volume
II
as
Method
I
for
bitertanol
(
M.
Bradley,
9/
15/
92).
The
method
has
been
received
by
FDA,
however,
it
has
not
been
compiled
into
PAM
Volume
II
as
of
yet.

860.1360
Multiresidue
Methods
Bitertanol
Summary
Analytical
Chemistry
and
Residue
Data
DP
Barcode:
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of
17
There
was
no
information
in
the
review
documents
regarding
submittal
of
data
for
FDA
multiresidue
methods
by
the
petitioner.
However,
the
FDA
PESTDATA
database
dated
11/
2001
(
PAM
Volume
I,
Appendix
I)
indicates
that
bitertanol
was
completely
recovered
using
Multiresidue
Method
Section
302
(
Protocol
D).

860.1380
Storage
Stability
Storage
stability
data
for
bitertanol
in/
on
bananas
have
not
been
submitted
by
the
registrant,
therefore,
storage
stability
data
are
required
(
HED
SOP
98.6).
No
information
on
the
stability
of
residues
in/
on
bananas
during
cold
storage
have
been
submitted.
Additionally,
no
data
were
provided
on
how
long
banana
samples
from
the
submitted
field
trials
were
stored
prior
to
analysis.

860.1400
Water,
Fish,
and
Irrigated
Crops
Bitertanol
is
not
intended
for
direct
use
on
water
and
aquatic
food
and
feed
crops;
therefore,
no
residue
chemistry
data
are
required
under
this
guideline
topic.

860.1460
Food
Handling
Bitertanol
is
not
intended
for
use
in
food­
handling
establishments;
therefore,
no
residue
chemistry
data
are
required
under
this
guideline
topic.

860.1480
Meat,
Milk,
Poultry,
and
Eggs
Bitertanol
is
not
intended
for
application
to
livestock
exported
to
the
U.
S.
In
addition,
there
are
no
animal
feedstuffs
associated
with
bananas.
Therefore,
no
residue
chemistry
data
are
required
under
this
guideline
topic.

860.1500
Crop
Field
Trials
Residue
data
for
bananas
grown
in
Costa
Rica
and
Honduras
were
provided
by
the
petitioner.
The
petitioner
indicated
that
these
two
countries
are
the
only
ones
where
bitertanol
would
be
used.
Bitertanol
was
applied
to
both
bagged
and
unbagged
bunches
of
green
and
ripe
bananas
at
a
rate
of
4.2
oz
ai/
A/
application,
the
maximum
rate
indicated
in
the
product
label.
Samples
of
peel,
pulp,
and
whole
fruit
were
collected
3
days
after
the
last
of
9
treatments
and
0
days
after
the
last
of
12
treatments.
Washed
and
unwashed
samples
were
analyzed
for
bitertanol
by
Method
54166,
with
modifications.
No
data
were
provided
on
how
long
the
samples
were
stored
prior
to
analysis.
Control
samples
of
washed
or
unwashed
green
peel,
ripe
peel,
green
pulp,
and
ripe
pulp
had
no
detectable
(<
0.01
ppm)
residues
of
bitertanol.
Recoveries
for
control
samples
of
peel
and
pulp
from
green
and
ripe
bananas
fortified
at
levels
of
0.02
­
0.10
ppm
were
56
to
120%
(
A.
Smith,
PP#
2E2756,
1/
28/
83).

Residue
data
were
reported
for
both
washed
and
unwashed
samples
of
bagged
and
unbagged
bananas.
The
results
are
summarized
below
in
Table
7.
All
residues
identified
in
the
bagged
samples
were
below
the
tolerance
level
of
0.2
ppm.
In
the
bagged
banana
trials,
after
9
applications
of
bitertanol,
the
highest
residue
in
a
washed
sample
was
0.5
ppm
(
green
and
ripe
Bitertanol
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and
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Data
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peel)
and
the
highest
residue
in
an
unwashed
sample
was
0.01
ppm
(
green
pulp).
After
12
applications
of
bitertanol,
the
highest
residue
in
a
washed
sample
was
0.15
ppm
(
green
peel)
and
the
highest
residue
in
an
unwashed
sample
was
0.12
ppm
(
ripe
peel).
Residues
were
detected
above
the
tolerance
level
of
0.2
ppm
in
the
unbagged
samples.
In
the
unbagged
banana
trials,
the
highest
residues
detected
after
9
applications
were
0.45
ppm
(
ripe
peel)
in
washed
samples
and
0.53
ppm
(
green
peel)
in
unwashed
samples.
After
12
applications,
the
highest
residues
detected
were
0.73
ppm
(
green
peel)
in
washed
samples
and
0.76
ppm
(
green
peel)
in
unwashed
samples.
With
few
exceptions,
residues
were
higher
in
washed
samples
than
in
unwashed
samples
for
both
bagged
and
unbagged
bananas.
No
explanation
was
provided
for
the
higher
residues
found
in
washed
samples.

The
petitioner
originally
had
requested
the
establishment
of
a
tolerance
for
residues
of
bitertanol
at
0.5
ppm.
However,
based
on
the
results
of
the
field
trials,
HED
concluded
that
a
tolerance
of
0.5
ppm
was
excessive
and
recommended
that
a
tolerance
of
0.2
ppm
be
proposed
(
A.
Smith,
Memorandum,
1/
28/
83).
The
petitioner
submitted
a
revised
tolerance
petition
proposing
a
tolerance
for
residues
of
bitertanol
of
0.2
ppm,
which
was
later
accepted
by
HED
(
A.
Smith,
PP#
2E2756,
9/
14/
83).
In
order
to
harmonize
with
Codex,
the
established
tolerance
should
be
increased
to
0.5
ppm.

It
is
noted
that
the
number
of
trials,
location
of
the
trials
within
the
countries
were
not
specified,
and
the
formulation
type
was
not
specified.
The
petitioner
had
originally
proposed
the
use
of
a
50%
WP
and
a
30%
emulsifiable
concentrate
(
Baycor
®
300
EC).
The
use
of
the
emulsifiable
concentrate
formulation
was
later
withdrawn
by
the
registrant
(
G.
E.
Brussell,
PP#
2E2756,
10/
13/
83).

At
the
time
the
import
tolerance
for
bitertanol
on
bananas
was
established,
HED
provided
caseby
case
advice
on
adapting
data
requirements
for
field
trials
to
import
situations.
Since
then,
guidance
on
data
requirements
for
import
tolerance
petitions
has
been
issued.
In
the
Federal
Register
of
June
1,
2000
(
65
FR
35069;
FRL­
6559­
30),
EPA
provided
detailed
guidance
on
applying
current
U.
S.
data
requirements
for
the
establishment
or
continuance
of
tolerances
for
pesticide
residues
in
or
on
imported
foods.
In
addition,
in
2003,
Canada,
Mexico
and
the
United
States
jointly
issued
a
guidance
document
on
the
data
requirements
needed
to
meet
the
North
American
Free
Trade
Agreement
(
NAFTA)
standards
for
the
establishment
of
pesticide
import
tolerances
or
maximum
residue
levels
in
the
NAFTA
countries
(
68
FR
18638;
FRL­
7299­
1).
The
NAFTA
guidance
document
is
consistent
with
the
2000
U.
S.
guidance.
In
general,
the
residue
chemistry
requirements
for
import
tolerances
listed
in
the
NAFTA
guidance
document
are
similar
to
those
for
any
other
tolerance
issued
by
the
NAFTA
countries.
However,
the
NAFTA
guidance
document
details
a
procedure
for
determining
the
minimum
number
and
location
of
field
trials,
based
on
the
maximum
consumption
of
the
commodity
as
a
percentage
of
the
U.
S.,
Canadian,
or
Mexican
diet,
and
the
maximum
relative
amount
imported
into
the
U.
S.,
Canada,
or
Mexico
from
outside
of
North
America.
The
NAFTA
guidance
document
also
indicates
that
field
trials
generally
will
need
to
be
conducted
in
all
countries
whose
exports
comprise
at
least
5%
of
the
total
amount
of
a
specific
commodity
imported
into
any
of
the
North
American
countries
where
a
tolerance
is
being
sought.
It
is
noted
that
the
field
trials
currently
being
conducted
with
the
SC
formulation
should
adhere
to
all
guidance
documents.
Bitertanol
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and
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Data
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Table
7.
Summary
of
Residues
from
the
Crop
Field
Trials
with
Bitertanol.

Crop
Matrix
Applic.
Rate
(
lb
ai/
A)
Number
of
Applications
PHI
(
days)
Residues
(
ppm)

Bagged
Unbagged
Washed
samples
Unwashed
samples.
Washed
samples
Unwashed
samples.

Green
peel
4.2
oz
ai/
A
9
3
0.05
<
0.01
0.41
0.53
Green
pulp
0.01
0.01
0.09
0.11
Green
fruit
0.03
<
0.01
0.22
0.24
Ripe
peel
0.05
<
0.01
0.45
0.25
Ripe
pulp
0.02
<
0.01
0.11
0.06
Ripe
fruit
0.03
<
0.01
0.23
0.13
Green
peel
4.2
oz
ai/
A
12
0
0.05,
0.15
0.04
0.09­
0.73
0.10­
0.76
Green
pulp
0.01,
0.02
0.01
0.03,
0.17
0.03,
0.08
Green
fruit
0.03,
0.06
0.02
0.05,
0.36
0.06­
0.33
Ripe
peel
0.03­
0.08
0.03­
0.12
0.05,
0.51
0.03­
0.32
Ripe
pulp
<
0.01,
0.02
0.01
0.02,
0.14
<
0.01,
0.08
Ripe
fruit
0.01­
0.04
0.02­
0.05
0.03­
0.28
0.01­
0.17
860.1520
Processed
Food
and
Feed
There
are
no
processed
commodities
associated
with
bananas.
Therefore,
no
residue
chemistry
data
are
required
under
this
guideline
topic.

860.1650
Submittal
of
Analytical
Reference
Standards
An
analytical
reference
standard
for
bitertanol
was
submitted
by
Bayer
in
December
of
2004
and
expires
October
of
2010.
The
standard
is
available
at
the
EPA
National
Pesticide
Standards
Repository.

860.1850
Confined
Accumulation
in
Rotational
Crops
Rotational
crop
studies
are
not
required
for
uses
of
pesticides
on
bananas
(
HED
SOP
96.6).

860.1900
Field
Accumulation
in
Rotational
Crops
Rotational
crop
studies
are
not
required
for
uses
of
pesticides
on
bananas
(
HED
SOP
96.6).

Tolerance
Reassessment
Summary
The
tolerance
for
residues
of
bitertanol
in/
on
plant
commodities
is
expressed
in
terms
of
residues
of
bitertanol
per
se
[$­([
1,1
'­
biphenyl]­
4­
yloxy)­"­(
1,1­
dimethylethyl)­
1H­
1,2,4­
triazole­
1­
Bitertanol
Summary
Analytical
Chemistry
and
Residue
Data
DP
Barcode:
302882
15
of
17
ethanol].

A
summary
of
the
bitertanol
tolerance
reassessment
for
bananas
is
presented
in
Table
8.

Tolerances
Listed
Under
40
CFR
§
180.457:

A
tolerance
has
been
established
under
40
CFR
§
180.457
for
residues
of
bitertanol
in/
on
bananas
imported
into
the
U.
S.
Field
trials
conducted
in
Costa
Rica
and
Honduras
showed
residues
below
the
existing
tolerance
level
of
0.2
ppm.
In
order
to
harmonize
with
Codex,
the
established
tolerance
should
be
increased
to
0.5
ppm.

Since
the
tolerance
for
bitertanol
is
an
import
tolerance,
it
should
be
listed
in
a
separate
subsection
of
40
CFR
indicating
that
there
are
no
U.
S.
registrations
for
bitertanol.

Table
8.
Tolerance
Summary
for
Bitertanol.

Commodity
Established/
Proposed
Tolerance
(
ppm)
Recommended
Tolerance
(
ppm)
Comments
[
correct
commodity
definition]

Banana
(
whole)
0.20
(
established)
0.5
Tolerance
should
be
listed
in
a
separate
subsection
of
40
CFR
indicating
that
there
are
no
U.
S.
registrations
associated
with
bitertanol.
[
Banana]

Codex/
International
Harmonization
The
Codex
Alimentarius
Commission
has
established
a
maximum
residue
limit
(
MRL)
for
bitertanol
residues
in/
on
bananas
at
0.5
mg/
kg.
The
Codex
MRL
for
bitertanol
is
expressed
in
terms
of
residues
of
bitertanol
only,
as
is
the
U.
S.
tolerance
expression.
Various
enforcement
methods
are
listed
for
bitertanol
under
the
Codex
system
including
PAM
Multiresidue
Method
Section
302
(
Protocol
D).

It
is
EPA's
policy
to
harmonize
its
tolerances
with
the
levels
established
by
Codex
provided
that
the
Agency
has
sufficient
information
to
make
a
determination
that
the
Codex
MRLs
will
be
protective
of
the
health
of
the
U.
S.
public
and
meet
FFDCA
standards.
FQPA
requires
EPA
to
publish
a
notice
for
public
comment
whenever
the
Agency
establishes
a
tolerance
that
differs
from
an
established
Codex
MRL.
The
established
tolerance
should
be
reassessed
to
0.50
ppm
to
harmonize
with
Codex
as
the
dietary
exposure
and
risk
are
not
of
concern
(
S.
Ary,
D302880,
11/
2/
2005).

Bibliography
NAFTA
Guidance
Document
on
Data
Requirements
for
Tolerances
on
Imported
Commodities.
April
2003.
(
http://
yosemite.
epa.
gov/
opp/
naftatwg.
nsf/
0/
ff1cbe90259cd6b985256d0900705b7e/$
FILE/
NAFT
A%
20Import%
20Tolerances%
20Document.
PDF)
Bitertanol
Summary
Analytical
Chemistry
and
Residue
Data
DP
Barcode:
302882
16
of
17
65
FR
35069.
Pesticides;
Guidance
on
Pesticide
Import
Tolerances
and
Residue
Data
for
Imported
Food;
Request
for
Comment.
June
1,
2000
(
Volume
65,
Number
106).
(
http://
www.
epa.
gov/
fedrgstr/
EPA­
PEST/
2000/
June/
Day­
01/
p13708.
htm)

68
FR
18638.
Pesticides;
North
American
Free
Trade
Agreement
Guidance
Document
on
Requirements
for
Tolerances
on
Imported
Commodities;
Notice
of
Availability.
April
16,
2003
(
Volume
68,
Number
73).
(
http://
www.
epa.
gov/
fedrgstr/
EPA­
PEST/
2003/
April/
Day­
16/
p9338.
htm)

HED
Standard
Operating
Procedure
(
SOP)
98.6.
Data
requirements
for
Import
Tolerances
(
12/
3/
1998).

Study
Citations
Table
9.
Agency
Memoranda
Citations.

Date
Barcode
ID
Number
From
To
MRID
Nos.
Subject
6/
30/
1980
PP#
0G2311
E.
Zager
H.
M.
Jacoby
00025731,
00025734,
00025716,
00071187
PP#
0G2311.
Baycor
®
on
apples,
pears
and
peanuts.
Evaluation
of
Analytical
Methods
and
Residue
Data.

1/
28/
1983
PP#
2E2756
A.
Smith
H.
M.
Jacoby
00071186,
00071188,
00114273
PP#
2E2756:
Baycor
®
in
Bananas.
Evaluation
of
residue
data
and
analytical
method.

3/
22/
1983
PP#
2E2756
A.
Burns
A.
Smith
00025716,
00071187
Report
on
Method
trial.

4/
27/
1983
PP#
2E2756
A.
Smith
H.
M.
Jacoby/
Toxicology
Branch
00025716,
00071187
PP#
2E2756:
Baycor
®
in
Bananas.
Report
on
Method
trial.

8/
10/
1983
PP#
2E2756
G.
E.
Brussell
Mobay
Chemical
Corporation
H.
M.
Jacoby
Baycor
®
50%
Wettable
Powder
and
Baycor
®

300
EC.
Pesticide
Petition
No.
2E2756.
Tolerance
for
Baycor
®
in
or
on
Bananas.

9/
14/
1983
PP#
2E2756
A.
Smith
H.
M.
Jacoby
PP#
2E2756:
Baycor
®
in
Bananas.
Amendment
of
5/
26/
83.

10/
13/
1983
PP#
2E2756
G.
E.
Brussell
Mobay
Chemical
Corporation
H.
M.
Jacoby
Baycor
®
on
Bananas.
Pesticide
Petition
No.
2E2756
9/
15/
1992
M.
Bradley
A.
Marcotte
FDA
Letter
to
FDA.
Submission
of
Method
I
for
bitertanol
for
inclusion
in
PAM
Volume
II.

11/
2/
2005
D302880
S.
Ary
C.
Jarvis
and
R.
Louie
Bitertanol.
Acute
and
Chronic
Dietary
Exposure
Assessments
for
the
Tolerance
Reassessment
Eligibility
Decision
(
TRED)
Document.

Master
Record
Identification
Numbers
00025716
Obrist,
J.
J.;
Nichols,
S.
S.
(
1979)
An
Interference
Study
for
the
Baycor(
TM)
Residue
Method
for
Apples
and
Peanuts:
Report
No.
68311.
(
Unpublished
study
received
Dec
21,
1979
under
3125­
EX­
168;
submitted
by
Mobay
Chemical
Corp.,
Kansas
City,
Mo.;
CDL:
099186­
F)

00071187
Obrist,
J.
J.;
Nichols,
S.
S.
(
1980)
An
Interference
Study
for
the
Baycor(
TM)
Residue
Method
for
Apples
and
Peanuts:
Report
No.
68311.
Rev.
(
Unpublished
study
received
Feb
2,
1981
under
1E2468;
submitted
by
Mobay
Chemical
Corp.,
Kansas
City,
Mo.;
CDL:
099905­
C)
Bitertanol
Summary
Analytical
Chemistry
and
Residue
Data
DP
Barcode:
302882
17
of
17
00025731
Puhl,
R.
J.;
Hurley,
J.
B.
(
1979)
The
Metabolism
of
Baycor(
TM)­
biphenyl­
UL­
14C
in
Apple
Fruit:
Report
No.
68305.
(
Unpublished
study
received
Dec
21,
1979
under
3125­
EX­
168;
submitted
by
Mobay
Chemical
Corp.,
Kansas
City,
Mo.;
CDL:
099185­
O)

00025734
Puhl,
R.
J.;
Hurley,
J.
B.
(
1979)
Metabolism
of
Baycor(
TM)­
biphenyl­
UL­
14C
in
Peanut
Plants:
Report
No.
68310.
(
Unpublished
study
received
Dec
21,
1979
under
3125­
EX­
168;
submitted
by
Mobay
Chemical
Corp.,
Kansas
City,
Mo.;
CDL:
099185­
R)

00071186
Mobay
Chemical
Corporation
(
1980)
Synopsis
of
Baycor:
Residue
Chemistry
on
Bananas.
Summary
of
studies
099905­
C
and
099905­
D.
(
Unpublished
study
received
Feb
2,
1981
under
1E2468;
CDL:
099905­
A)

00071188
Mobay
Chemical
Corporation
(
1980)
(
Residue
of
Baycor
(
TM):
Bananas):
Report
No.
68896.
(
Compilation;
unpublished
study,
including
report
nos.
68897,
68898,
68899
received
Feb
2,
1981
under
1E2468;
CDL:
099905­
D)

00114273
Mobay
Chemical
Corp.
(
1982)
Addition
No.
1
to
the
Brochure
Entitled:
Baycor
Residue
Chemistry
on
Bananas:
Document
No.
AS­
82­
2104.
(
Compilation;
unpublished
study
received
Sep
15,
1982
under
2E2756;
CDL:
071088­
A)
