UNITED
STATES
ENVIRONMENTAL
PROTECTION
AGENCY
WASHINGTON,
D.
C.
20460
OFFICE
OF
PREVENTION,
PESTICIDES
AND
TOXIC
SUBSTANCES
MEMORANDUM
Date:
11/
02/
05
Subject:
Tridemorph
Tolerance
Reassessment
Eligibility
Decision
(
TRED).
Summary
of
Analytical
Chemistry
and
Residue
Data.

DP
Number:
D322129
PC
Code:
121401
40
CFR
§
180.372
Chemical
Class:
morpholine
fungicide
From:
Gary
Otakie,
Chemist
Reregistration
Branch
4
Health
Effects
Division
(
7509C)

Through:
Susan
V.
Hummel,
Branch
Senior
Scientist
Reregistration
Branch
4
Health
Effects
Division
(
7509C)

To:
Rebecca
Daiss,
Risk
Assessor
Reregistration
Branch
4
Health
Effects
Division
(
7509C)

and
Rosanna
Louie,
Chemical
Review
Manager
Reregistration
Branch
2
Special
Review
&
Reregistration
Division
(
7508C)

Attached
is
the
Residue
Chemistry
Chapter
for
the
Tridemorph
Tolerance
Reassessment
Eligibility
Decision
(
TRED)
document.
This
chapter
was
completed
by
Versar,
Inc.
under
supervision
of
HED
and
has
undergone
secondary
review/
modification
in
Reregistration
Branch
4
for
consistency
with
current
EPA
policies
and
add
new
information.

The
existing
residue
chemistry
database
for
tridemorph
is
incomplete.
No
data
will
be
required
if
all
tolerances
are
revoked.
However,
if
tolerances
are
to
remain
to
cover
import
uses,
additional
data
are
required.

cc
:
Chem
F,
Chron
G.
Otakie
RDI:
Team:
10/
19
/
05;
SVH
11/
02/
05
GO,
Gary
Otakie,
Rm.
824A,
CM2,
305­
6991,
mail
code
7509C
Tridemorph
Summary
of
Analytical
Chemistry
and
Residue
Data
Barcode:
D322129
2
of
18
Executive
Summary
Tridemorph
(
2,6­
dimethyl­
4­
tridecylmorpholine)
is
a
fungicide
registered
in
South
America
for
the
control
of
Sigatoka
disease
in
or
on
bananas.
Tridemorph
is
formulated
as
a
emulsifiable
concentrate
(
EC)
containing
6.26
lb
ai/
A
in
the
end­
use
product,
Calixin.
The
formulation
is
to
be
applied
at
a
the
rate
of
0.33­
0.40
lb
ai/
A
(
0.375­
0.450
kg
ai/
ha)
with
0.5­
1.1
gal
oil/
A
(
5­
10
L
oil/
ha)
and
sufficient
water
to
obtain
a
volume
of
2.7
gal/
A
(
25
L/
ha).
Most
applications
are
aerial.
Depending
on
the
degree
of
infection
and
the
season,
applications
are
to
be
made
every
2­
4
weeks.
There
is
no
established
pre­
harvest
interval
(
PHI).
Currently,
there
are
no
U.
S.
registrations
for
tridemorph.

A
petition
(
PP#
1H5281)
was
submitted
by
BASF
Wyandotte
Corporation
to
establish
a
tolerance
of
50
ppm
for
the
residues
of
tridemorph
in/
on
dried
tea.
However,
the
proposed
tolerance
was
not
established
due
to
significant
toxicological
data
gaps,
teratogenicity
concerns
and
the
presence
of
a
morpholine
moiety
which
can
easily
be
nitrosated
by
ingested
dietary
nitrites
at
acidic
pH's
of
the
stomach
(
G.
Ghali,
4/
13/
82).
Nitrosamine
data
were
later
submitted
and
reviewed..
No
detectable
nitrosamines
were
found
(
R.
J.
Hummel,
10/
25/
77)

The
nature
of
terminal
residue
in
bananas
was
considered
adequately
defined
based
on
a
field
metabolism
study
using
ring­
labeled
14C­
tridemorph
conducted
on
a
banana
plantation
in
Costa
Rica.
Tridemorph
per
se
is
the
residue
of
concern.
As
there
are
no
uses
on
animal
feed,
the
Agency
concluded
that
the
metabolism
in
animals
was
adequately
understood,
and
the
intended
use
will
be
Category
3
of
Section
180.6(
a)
with
respect
to
secondary
residues
in
meat,
milk,
poultry
and
eggs.

Adequate
tolerance
enforcement
methods
are
listed
in
PAM
Volume
II
for
the
determination
of
tridemorph
residues
of
concern.
The
analytical
enforcement
analytical
method
is
a
colorimetric
method
based
on
the
formation
of
a
chloroform
soluble
tridemorph/
methyl
orange
addition
complex.
Residues
of
tridemorph
are
confirmed
through
a
GC/
MS
procedure.
The
analytical
method
is
also
suitable
for
the
determintation
of
2,6­
dimethylmorpholine
(
DMM),
a
metabolite
of
tridemorph.

A
tolerance
has
been
established
under
40
CFR
§
180.372
for
residues
of
tridemorph
in
or
on
bananas
imported
into
the
U.
S.
at
0.1
ppm.
Three
field
trials
were
conducted
in
Costa
Rica
using
aerial
application
of
tridemorph
to
bagged
banana
crops
at
0.33
lb
ai/
A
(
10­
21
applications).
Two
of
the
three
studies
resulted
in
no
detectable
residues
of
tridemorph
(<
0.05
ppm)
in
either
the
peels
or
pulp
of
bananas.
In
the
third
study,
tridemorph
residues
ranged
from
nondetectable
(<
0.01
ppm)
to
barely
detectable
(
0.01
ppm)
in
the
pulp
and
from
<
0.01
to
0.1
ppm
in
the
peels.
Another
study
was
conducted
in
an
unknown
location
on
presumably
bagged
bannanas.
At
0.33
lb
ai/
A
(
19­
21
applications
over
2
years),
residues
of
tridemorph
or
its
metabolite
DMM
were
not
detected
in
either
pulp
or
peel
(<
0.05
ppm).
In
twelve
field
trials
conducted
in
2002
in
Colunbia
(
2),
Guatemala(
1),
Costa
Rica
(
2),
Mexico
(
1),
Ecuador
(
2),
Honduras
(
2),
and
Martinique
(
2)
epoxiconazle
(
EC)
and
tridemorph
(
OL)
were
applied
to
both
bagged
and
unbagged
bannans
with
10
foliar
applications
of
tridemorph
at
0.338­
0.518
kg
ai/
ha/
application.
Residues
of
tridemorph
in
the
main
tests
were
<
0.05
ppm
(<
LOQ)
in/
on
all
samples
of
bagged
whole
bananas
Tridemorph
Summary
of
Analytical
Chemistry
and
Residue
Data
Barcode:
D322129
3
of
18
(
n=
12)
harvested
at
0
DAT
and
in
all
associated
subsamples
of
pulp
(
Table
C.
3.3).
Residues
were
also
<
0.05
ppm
in/
on
10
out
of
12
peel
samples,
and
were
0.066
and
0.085
ppm
in/
on
the
remaining
2
samples
of
peel
from
bagged
fruits.
For
unbagged
fruit
samples
harvested
at
0­
DAT,
residues
of
tridemorph
were
<
0.05
ppm
in/
on
7
out
of
12
samples
of
whole
fruit;
residues
in/
on
the
remaining
5
samples
were
0.054­
0.628
ppm.
In
pulp
from
unbagged
fruits,
residues
were
<
0.05
ppm
in/
on
11
subsamples
and
0.066
ppm
in
one
subsample.
In
peel
from
unbagged
fruits,
residues
were
<
0.05
ppm
in/
on
7
subsamples
and
0.052­
0.907
ppm
in
5
subsamples.

Average
tridemorph
resides
were
0.114
and
0.025
ppm
in/
on
unbagged
and
bagged
samples
of
whole
bananas
(
RAC),
respectively,
and
0.028
and
0.025
ppm
in
pulp
samples
from
unbagged
and
bagged
fruits.

For
tridemorph,
residue
data
on
unbagged
whole
fruit
and
peel
samples
from
one
test
indicated
that
residues
of
tridemorph
generally
declined
at
longer
post­
treatment
intervals.
In
this
test,
maximum
whole
fruit
residues
occurred
at
5
DAT
(
0.06
ppm)
and
then
declined
to
<
0.05
ppm
by
7
DAT.
Maximum
peel
residues
occurred
at
3
DAT
(
0.093
ppm)
and
then
declined
to
<
0.05
ppm
by
10
DAT.

For
tridemorph
the
highest
residues
were
clearly
associated
with
the
two
field
trials
conducted
in
Martinique,
which
used
applications
in
100%
spray
oil
to
the
underside
of
the
canopy.
For
these
two
tests,
residues
of
tridemorph
were
0.066­
0.085
ppm
in/
on
bagged
fruits
and
0.638­
0.907
ppm
in/
on
unbagged
fruits.

While
in
general
the
residue
chemistry
requirements
for
import
tolerances
are
similar
to
those
for
any
other
tolerance
issued
by
the
NAFTA
countries,
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.
Based
on
this
new
guidance,
for
import
tolerances
in
the
U.
S.
for
bananas,
12
field
trials
are
required.
The
12
field
trials
should
be
split
between
Columbia
(
2),
Ecuador
(
3),
Honduras
(
2),
and
Guatemala
(
2).

It
should
be
noted
that
the
crop
field
trials
were
conducted
prior
to
the
issuance
of
a
guidance
document
by
NAFTA
countries
on
the
data
requirements
for
import
tolerances.
Although
the
distribution
of
the
banana
field
trials
does
not
exactly
match
the
distribution
recommended
by
the
Agency,
the
12
field
trails
conducted
at
1x
during
2002
in
Columbia
(
2
tests),
Guatemala
(
1
test),
Costa
Rica
(
2
tests),
Mexico
(
1
test),
Ecuador
(
2
tests),
Honduras
(
2
tests),
and
Martinique
(
2
tests)
are
adequate.

Regulatory
Recommendations
and
Residue
Chemistry
Deficiencies
A
tolerance
has
been
established
under
40
CFR
§
180.372
for
the
residues
of
tridemorph
in
or
on
bananas
imported
into
the
U.
S.
at
0.1
ppm.
Based
on
new
residue
data,
the
established
tolerance
of
0.1
ppm
in/
on
banana
must
be
increased
to
1.0
ppm.
HED
supports
a
revised
import
tolerance
of
1.0
ppm
in/
on
banana,
provided
that
the
following
deficiencies
and
data
gaps
are
resolved:
Tridemorph
Summary
of
Analytical
Chemistry
and
Residue
Data
Barcode:
D322129
4
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18
°
There
was
no
information
in
the
review
documents
regarding
submittal
of
data
for
FDA
multiresidue
methods
by
the
petitioner.
Tridemorph
was
not
listed
in
the
FDA
PESTDATA
database
dated
11/
01
(
PAM
Volume
I,
Appendix
I).
Data
are
required
for
FDA
multiresidue
methods.

°
Acceptable
frozen
storage
stability
data
for
tridemorph
in
bananas
for
a
one
year
period
must
be
submitted.

°
Product
Chemistry
data
must
be
provided.

A
human
health
risk
assessment
is
forthcoming.

Background
The
nomenclature
of
tridemorph
is
listed
in
Table
1,
the
physicochemical
properties
of
tridemorph
are
listed
in
Table
2,
and
the
chemical
names
and
structures
of
tridemorph
and
metabolites
are
listed
in
Table
3.
Tridemorph
Summary
of
Analytical
Chemistry
and
Residue
Data
Barcode:
D322129
5
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18
TABLE
1.
Tridemorph
Nomenclature
Compound
Chemical
Structure
Common
name
Tridemorph
Trade
Name
Calixin
Company
experimental
name
BASF
2203F
IUPAC
name
2,6­
dimethyl­
4­
tridecylmorpholine
CAS
name
CAS:
2,6­
dimethyl­
4­
tridecylmorpholine
CAS
#
24602­
86­
6
Current
Food/
Feed
Site
Registration
No
U.
S.
registrations.
Registered
for
use
in/
on
bananas
in
South
America.

TABLE
2.
Physicochemical
Properties
of
the
Technical
Grade
Tridemorph
Parameter
Value
Reference
Melting
point/
range
NA
pH
NA
Density
NA
Water
solubility
(
20
/

C)
11.7
mg/
L
EEE
Branch
Review,
R.
Ney,
10/
20/
75,
00067847.

Solvent
solubility
(
mg/
L
at20
/

C)
Miscible
with
ordinary
organic
solvents
at
any
rate.
EEE
Branch
Review,
R.
Ney,
10/
20/
75,00067847.

Vapour
pressure
(
mPa)
at
20
/

C
6.4
Dissociation
constant
(
pKa)
NA
Octanol/
water
partition
coefficient
Log(
KOW)
NA
UV/
visible
absorption
spectrum
NA
Tridemorph
Summary
of
Analytical
Chemistry
and
Residue
Data
Barcode:
D322129
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18
O
NH
C
H
3
CH
3
TABLE
3.
Chemical
Names
and
Structures
of
Tridemorph
and
Metabolites
Company
Name
Chemical
Name
Structure
Tridemorph
2,6­
dimethyl­
4­
tridecylmorpholine
DMM
2,6­
dimethylmorpholine
860.1200
Directions
for
Use
Product
List
Currently,
there
are
no
U.
S.
registrations
for
tridemorph.
However,
tridemorph,
contained
in
the
end­
use
product,
Calixin,
is
a
emulsifiable
concentrate
containing
6.26
lb
ai/
A
registered
for
use
on
bananas
in
South
America
(
N.
Dodd,
9/
8/
83).
According
to
a
6/
24/
76
EPA
memo
from
R.
J.
Hummel,
tridemorph
is
registered
for
use
in
Columbia,
Costa
Rica,
Dominican
Republic,
Ecuador,
and
Guatemala.
It
is
also
proposed
for
use
in
Honduras,
but
no
registration
is
required
for
this
country.
Calixin
is
manufactured
by
BASF
Corporation.

Use
Patterns
A
summary
of
the
direction
for
the
use
of
tridemorph
is
presented
in
Table
4.
For
control
of
Sigatoka
disease
in
bananas,
tridemorph
is
to
be
applied
at
a
the
rate
of
0.33­
0.40
lb
ai/
A
with
0.5­
1.1
gal
oil/
A
(
5­
10
L
oil/
ha)
and
sufficient
water
to
obtain
a
volume
of
2.7
gal/
A
(
25
L/
ha).
Most
applications
are
aerial.
Depending
on
the
degree
of
infection
and
the
season,
applications
are
to
be
made
every
2­
4
weeks.
There
is
no
established
PHI
(
R.
J.
Hummel,
2/
25/
76).

A
tabular
summary
of
the
chemistry
science
assessments
is
presented
in
Table
5.
The
conclusions
listed
in
Table
5
regarding
the
reregistration
eligibility
of
tridemorph
food/
feed
uses
are
based
on
the
use
patterns
registered
by
the
producer.
When
end­
use
product
data
call
in's
(
DCIs)
are
developed
(
e.
g.,
at
issuance
of
the
RED),
the
Registration
Division
(
RD)
should
require
that
all
end­
use
product
labels
(
e.
g.,
MAI
labels,
SLNs,
and
products
subject
to
the
generic
data
exemption)
be
amended
such
that
they
are
consistent
with
the
basic
producer
labels.
Tridemorph
Summary
of
Analytical
Chemistry
and
Residue
Data
Barcode:
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Tridemorph
Summary
of
Analytical
Chemistry
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Residue
Data
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18
TABLE
4.
Summary
of
Directions
for
Use
of
Tridemorph1
Application
Timing
°
Type
°
Equipment
Formulation
Applic.
Rate
(
lb
ai/
A)
Max.
No.
Applic.
per
Season
Max.
Seasonal
Applic.
Rate
(
lb
ai/
A)
PHI
(
days)
Use
Directions
and
Limitations
Bananas
Depending
on
the
degree
of
infection
and
the
season,
applications
are
to
be
made
every
2­
4
weeks
°
Aerial
°
Aircraft
Calixin
EC
0.33­
0.40
lb
ai/
A
NR
NR
NR
Do
not
apply
Calixin
to
bananas
grown
for
the
U.
S.
market
unless
they
are
to
be
bagged
on
the
plant
according
to
usual
and
common
practice.

Ground
foliar
Calixin
86
(
OL)
0.37­
0.39
lb/
ai/
A
(
430
g
ai/
ha/
ap
plication
)
10
with
RTI
of
12­
15
days
4.0
lb
ai/
A
0
None
(
no
restriction
for
use
on
unbagged
bananas)

1
Currently,
there
are
no
U.
S.
registrations
for
tridemorph.
A
label
for
Calixin,
registered
for
use
in
South
America,
was
not
available.
Data
contained
in
this
table
were
compiled
from
Agency
memos
(
R.
J.
Hummel,
2/
25/
76
and
R.
J.
Hummel,
6/
24/
76)
A
proposed
label
submitted
for
#
7E4885,
epoxiconazole
on
bananas
uses
a
duel
ai
product
which
includes
tridemorph
(
A.
Acierto,
xx/
xx/
05,
G.
Otakie,
11/
02/
05).

TABLE
5.
Residue
Chemistry
Science
Assessment
for
Reregistration
of
Tridemorph
GLN
Data
Requirements
Current
Tolerances
(
ppm)
[
§
180.372]
Additional
Data
Needed?
MRID
Nos.

860.1200:
Directions
for
Use
N/
A
=
Not
Applicable
No
See
Table
4.

860.1300:
Nature
of
the
Residue
­
Plants
­
Bananas
N/
A
No
001513371
860.1300:
Nature
of
the
Residue
­
Animals
N/
A
No
001513372
860.1340:
Residue
Analytical
Method
­
Plant
Commodities
N/
A
No
000407113,
46574902,
46574903
­
Animal
Commodities
N/
A
No
None
860.1360:
Multiresidue
Method
N/
A
Yes4
None
860.1380:
Storage
Stability
Data
Tridemorph
Summary
of
Analytical
Chemistry
and
Residue
Data
Barcode:
D322129
TABLE
5.
Residue
Chemistry
Science
Assessment
for
Reregistration
of
Tridemorph
GLN
Data
Requirements
Current
Tolerances
(
ppm)
[
§
180.372]
Additional
Data
Needed?
MRID
Nos.

9
of
18
­
Plant
Commodities
N/
A
Yes5
None
­
Animal
Commodities
N/
A
No
None
860.1400:
Magnitude
of
the
Residue
­
Water,
Fish,
and
Irrigated
Crops
N/
A
No
None
860.1460:
Magnitude
of
the
Residue
­
Food
Handling
N/
A
No
None
860.1480:
Magnitude
of
the
Residue
­
Meat,
Milk,
Poultry,
Eggs
N/
A
No
001513376
860.1500:
Crop
Field
Trials
­
Bananas
0.1
Yes5
1353818,
464821017
860.1520:
Processed
Food/
Feed
­
Tea
N/
A
No
00067848
860.1650:
Submittal
of
Analytical
Reference
Standards
N/
A
No9
None
860.1850:
Confined
Accumulation
in
Rotational
Crops
N/
A
No
None
860.1900:
Field
Accumulation
in
Rotational
Crops
N/
A
No
None
1
The
nature
of
residue
in
plants
was
reviewed
in
R.
J.
Hummel,
2/
25/
76
and
R.
J.
Hummel,
10/
25/
77.
2
The
nature
of
residue
in
animals
was
reviewed
in
R.
J.
Hummel,
2/
25/
76.
3
The
MRID
number
was
found
in
the
MRID
bibliography
for
tridemorph.
No
MRID
or
accession
numbers
were
provided
in
the
EPA
reviews
of
the
analytical
methodologies
(
R.
J.
Hummel,
6/
24/
76).
4
Multiresidue
testing
data
have
not
been
submitted.
Tridemorph
is
not
listed
in
Pestrak
5
Storage
stability
data
were
not
provided.
The
banana
field
trial
residue
data
are
acceptable
pending
submission
of
supporting
storage
stability
data
for
tridemorph
residues
in
frozen
bananas
for
one
year.
6
Livestock
feeding
studies
were
reviewed
in
R.
J.
Hummel,
2/
25/
76.
7
Based
on
this
new
guidance,
for
import
tolerances
in
the
U.
S.
for
bananas,
12
field
trials
are
required.
Only
four
field
trials
had
been
submitted;
therefore,
additional
data
were
required.
In
acccordance
with
import
tolerance
guidance,
12
field
trials
should
be
split
between
Columbia
(
2),
Ecuador
(
3),
Honduras
(
2),
and
Guatemala
(
2).
However,
these
new
data
adequately
represents
the
major
banana
producing
countries
exporting
to
the
US.
8
The
MRID
number
was
found
in
the
MRID
bibliogrpahy
for
tridemorph.
No
MRID
or
accession
numbers
were
provided
in
the
EPA
reviews
of
the
crop
field
trials
(
in
R.
J.
Hummel,
2/
25/
76
and
R.
J.
Hummel,
10/
25/
77).
9
Replenish
standards
as
requested
by
the
repository,
including
all
residues
of
concern,
needed
by
the
enforcement
method.

860.1300
Nature
of
the
Residue
­
Plants
To
determine
whether
tridemorph
is
systemic,
ring­
labeled
14C­
tridemorph
was
applied
to
the
leaves
of
barley,
cucumbers
and
bananas.
Plants
were
sampled
at
various
intervals
and
analyzed
autoradiometrically.
In
barley
and
cucumbers,
tridemorph
was
absorbed
and
translocated
rapidly.
In
bananas,
translocation
was
slow
as
a
result
of
slow
penetration
of
the
leaf
surface
(
R.
J.
Hummel,
2/
25/
76).

A
banana
translocation
study
was
also
carried
out
in
Costa
Rica.
Banana
leaves
were
treated
with
either
unlabeled
or
ring­
labeled
14C­
tridemorph.
At
appropriate
intervals,
leaves
were
analyzed
either
by
the
proposed
analytical
method
or
by
radiometric
techniques
to
determine
both
the
speed
Tridemorph
Summary
of
Analytical
Chemistry
and
Residue
Data
Barcode:
D322129
10
of
18
of
leaf
penetration
and
translocation.
Tridemorph
was
found
to
rapidly
penetrate
into
leaves
and
remain
at
levels
>
2
ppm
for
at
least
4
weeks
after
treatment.
Partial
treatment
of
leaves
indicated
that
translocation
to
untreated
portions
of
the
leaves
was
relatively
slow.
The
petitioner
postulates
that
because
of
this
slow
rate
of
translocation,
no
residues
in
fruit
would
result
from
translocation
of
residues
from
the
treated
leaves
(
R.
J.
Hummel,
2/
25/
76).

Additionally,
a
field
metabolism
study
using
ring­
labeled
14C­
tridemorph
was
conducted
on
a
banana
plantation
in
Costa
Rica.
Banana
plants
which
contained
fruit
that
was
to
be
harvested
in
approximately
1
month
were
treated
with
14C­
tridemorph
five
times
at
weekly
intervals.
Applications
were
made
by
painting
the
upper
three
leaves
and
the
entire
fruiting
stem
with
a
formulation
consisting
of
300
mg
14C­
tridemorph,
20
mg
spray
oil,
0.25
mg
surfactant
and
approximately
300
mL
water.
Application
rates
were
10
mg/
m2
14C­
tridemorph.
After
the
first
two
applications,
the
stem
was
covered
with
a
polyethylene
bag
in
order
to
simulate
commercial
practice.
Shortly
after
the
last
application,
the
treated
leaves
and
fruiting
stems
were
harvested;
the
fruit
was
essentially
mature
and
at
a
stage
typical
of
commercial
harvest.
Leaves,
peels,
and
pulp
were
analyzed
for
total
activity
by
radiometric
techniques.
Total
radioactivity
(
expressed
as
tridemorph)
ranged
from
0.02­
0.04
ppm
in
pulp,
from
0.15­
0.31
ppm
in
peel
and
from
7­
33
ppm
in
leaves.
The
residues
in
leaves
and
peels
were
characterized
by
radiometric
TLC
and
confirmed
by
GC/
MS.
Of
the
extractable
activity,
87%
of
the
residues
in
leaves
partitioned
into
the
organic
phase.
The
major
component
of
this
phase
was
found
to
be
the
parent
compound
with
a
small
amount
of
polar
material.
The
majority
of
the
aqueous
soluble
activity
was
found
to
be
2,6­
dimethyl
morpholine
(
DMM).
The
residues
in
the
peel
was
also
found
to
be
primarily
tridemorph,
per
se,
with
traces
of
2,6­
dimethyl
morpholine
found
in
the
aqueous
phase.
No
attempt
was
made
to
characterize
the
trace
amount
of
residue
(
0.02
­
0.04
ppm)
in
the
pulp
(
R.
J.
Hummel,
2/
25/
76);
however,
HED
concluded
that
there
was
no
need
to
characterize
the
total
activity
equivalent
to
0.02­
0.04
ppm
in
banana
pulp
because
possible
residues
of
the
metabolite
2,6­
dimethylmorpholine
in
banana
pulp
at
these
levels
would
not
be
of
toxicological
concern
(
R.
D.
Coberly,
personal
communication,
5/
11/
76).

Because
toxicological
studies
have
indicated
that
morpholine
is
a
weak
carcinogen
and
the
concern
that
secondary
amines
and
nitrites
in
acid
situations
form
dinitrosamines,
nitrosamine
data
were
required
for
tridemorph.
Therefore,
residue
data
for
N­
nitroso­
2,6­
dimethyl
morpholine
(
NDMM)
on
tridemorph
treated
bananas
and
numerous
other
studies
related
to
nitrosation
of
DMM
were
submitted..
The
residue
data
indicated
that
no
detectable
residues
of
either
the
plant
metabolite
DMM
or
NDMM
were
found
in
tridemorph
treated
bananas.
Also,
residues
of
unsubtituted
morphaline
are
not
expected
to
be
present
in
tridemorph
treated
bananas
or
to
be
a
rat
metabolite
of
tridemorph
(
R.
J.
Hummel,
10/
25/
77).

The
Toxicology
Branch
determined
the
nature
of
terminal
residue
in
bananas
is
considered
adequately
defined;
tridemorph
per
se
is
the
residue
of
concern.
Tridemorph
Summary
of
Analytical
Chemistry
and
Residue
Data
Barcode:
D322129
11
of
18
860.1300
Nature
of
the
Residue
­
Livestock
A
balance
study
was
submitted
in
which
rats
were
given
a
single
oral
dose
of
14C­
tridemorph
at
a
rate
equivalent
to
20
mg/
kg
and
urine,
feces
and
expired
air
were
monitored
for
radioactivity.
The
rats
were
sacrificed
after
5
days
and
the
carcasses
analyzed
for
residual
activity.
Separate
experiments
were
conducted
in
which
bile
and
carcasses
were
monitored
for
activity
at
various
intervals
after
dosing.
Attempts
were
made
to
characterize
the
activity
in
urine,
feces
and
bile
by
TLC
and
MS.

Approximately
90%
of
the
ingested
activity
was
eliminated
in
the
excreta
within
5
days
of
dosing.
Urine
contained
about
43%,
feces
about
47%,
an
additional
1.5%
was
eliminated
as
14CO
2
and
3.5%
was
retained
in
the
carcass.
At
least
four
metabolites
of
tridemorph
were
detected
in
urine
and
two
in
bile
and
fecal
extracts.
One
of
these
was
tentatively
identified
as
the
N­
oxide
of
2,6­
dimethylmorpholine.
Only
negligible
amounts
of
tridemorph,
per
se,
were
eliminated;
the
plant
metabolite
2,6­
dimethyl­
morpholine
could
not
be
detected.
Incubation
of
extracts
with
Bglucuronidase
did
not
affect
the
pattern
of
metabolites
on
TLC
(
R.
J.
Hummel,
2/
25/
76).

As
there
are
no
tolerances
for
animal
feed
established,
no
additional
livestock
metabolism
data
are
needed.

860.1340
Residue
Analytical
Methods
The
enforcement
analytical
method
is
a
colorimetric
method
based
on
the
formation
of
a
chloroform
soluble
tridemorph/
methyl
orange
addition
complex.
HED
concluded
that
the
original
colorimetric
method
submitted
was
not
adequate
without
the
submittal
of
data
demonstrating
that
residues
of
tridemorph
can
be
determined
in
the
presence
of
all
other
pesticides
with
tolerances
for
bannanas
or
a
confirmatory
method.
In
response,
the
petitioner
submitted
both
the
results
of
a
specificity
study
and
a
GC/
MS
confirmatory
method.
HED
concluded
that
the
method
is
adequate
to
enforce
a
tolerance
of
0.1
ppm
when
coupled
with
the
GC/
MS
confirmatory
procedure.
In
addition
to
modifying
the
procedure
with
the
addition
of
the
confirmatory
method,
the
petitioner
revised
the
original
method
so
that
is
also
capable
of
determining
residue
of
DMM.
In
the
revised
method,
inital
extraction
is
performed
with
50%
aqueous
acetone
and
then
residues
are
partitioned
between
chloroform
and
water.
Tridemorph
is
organo­
soluble
and
partitions
into
the
chloroform
layer;
2,6­
dimethylmorpholine
(
DMM)
is
water
soluble
and
partitions
into
the
aqueous
phase.
Tridemorph
residues
are
extracted
into
hexane
and
cleaned­
up
by
alumina
column
chromatography.
The
eluate
is
taken
up
in
water
and
a
buffer
solution,
methyl
orange
and
chloroform
are
added.
The
chloroform
layer
is
drawn
off
with
great
care
taken
to
avoid
contamination
with
the
aqueous
phase.
The
tridemorph/
methyl
orange
addition
complex
is
cleaved
by
extraction
with
1N
HCl.
The
released
methyl
orange
is
extracted
into
the
aqueous
acid
phase
and
determined
colorimetrically
at
510
nm.
In
the
procedure
for
determining
DMM,
residues
are
extracted
from
the
aqueous
phase
by
repetitive
extraction
with
chloroform,
cleanedup
by
liquid/
liquid
partitioning
and
alumina
column
chromatography,
and
reacted
with
4­
bromobenzoyl
chloride.
The
resulting
derivative,
N­
4'­
bromobenzoyl­
2,6­
dimethylmorpholine,
is
cleaned­
up
by
silica
gel
column
chromatography
and
determined
by
ECGC.
Under
the
GLC
conditions,
separate
peaks
for
cis­
and
trans­
isomers
are
observed
(
R.
J.
Hummel,
6/
24/
76).
Tridemorph
Summary
of
Analytical
Chemistry
and
Residue
Data
Barcode:
D322129
12
of
18
The
petitioner
reported
recoveries
of
80­
90%
from
grain,
straw,
bananas
and
cucumbers
fortified
with
tridemorph
at
levels
of
0.05­
1
ppm.
The
limit
of
detection
was
0.05
ppm
(
as
determined
by
the
petitioner)
and
0.01
ppm
(
as
determined
by
Delmonte
Corporation
who
also
used
this
method
on
bananas).
An
EPA
tryout
of
this
method
completed
on
whole
bananas
and
banana
pulp
at
tridemorph
fortification
levels
of
0.1
and
0.05
ppm,
respectively,
showed
corrected
recoveries
of
80­
90%.
Based
on
residues
of
0.04
to
0.05
ppm
detected
in
the
blanks,
the
indicated
sensitivity
of
the
method
is
0.1
ppm
(
K.
T.
Zee,
1/
8/
76).

This
method
was
determined
to
be
adequate
to
enforce
tolerances
for
combined
residues
of
tridemorph
and
its
metabolite
DMM.

A
LC/
MS/
MS
method
(
BASF
Method
Number
529/
0)
was
used
to
determine
residues
of
tridemorph
in
the
banana
crop
field
trials
(
MRID
46482101).
A
brief
description
of
the
method
follows.

Residues
of
tridemorph
are
extracted
by
initially
homogenizing
the
sample
with
MeOH:
water:
2N
HCl
(
80/
15/
5,
v/
v/
v).
An
equal
volume
of
water
is
then
added
and
the
sample
is
further
homogenized.
After
centrifuging,
residues
in
the
extract
are
partitioned
into
dichloromethane
and
concentrated
to
dryness.
Residues
are
then
redissolved
in
water/
acetonitrile
(
50/
50,
v/
v)
and
analyzed
by
HPLC
with
MS/
MS
detection.
The
HPLC
system
uses
a
reverse
phase
C
18
column
with
a
mobile
phase
gradient
of
water
to
acetonitrile,
each
containing
0.1%
formic
acid.
The
retention
time
for
tridemorph
is
­

8.2
min,
and
residues
were
detected
and
quantified
by
monitoring
the
m/
z
2986130
and
2986116
transitions.
The
validated
method
LOQ
is
0.05
ppm
for
residues
of
tridemorph
in/
on
bananas.
The
LOD
was
not
reported.

The
method
was
validated
concurrently
with
the
analysis
of
the
field
trial
samples
using
control
samples
of
whole
fruit,
pulp,
and
peel
fortified
with
tridemorph
at
0.05
and
0.50
ppm.

860.1360
Multiresidue
Methods
Tridemorph
is
not
listed
in
the
FDA
PESTDATA
database
dated
11/
01
(
PAM
Volume
I,
Appendix
I).
FDA
multiresidue
data
are
required.

860.1380
Storage
Stability
Storage
stability
data
for
tridemorph
have
not
been
submitted.
These
data
are
required.

860.1400
Water,
Fish,
and
Irrigated
Crops
Tridemorph
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
Tridemorph
is
not
intended
for
use
in
food­
handling
establishments;
therefore,
no
residue
Tridemorph
Summary
of
Analytical
Chemistry
and
Residue
Data
Barcode:
D322129
13
of
18
chemistry
data
are
required
under
this
guideline
topic.

860.1480
Meat,
Milk,
Poultry,
and
Eggs
Two
cattle
feeding
studies
were
submitted.
In
the
first
study,
two
dairy
cows
were
fed
a
daily
dose
of
0.5
g
tridemorph
for
14
days.
The
daily
dose
was
then
increased
to
1
g
for
an
additional
14
days
and
finally
to
1.5
g
for
the
concluding
14
days
of
the
study.
Samples
of
each
milking
were
analyzed
for
tridemorph
residues
using
a
method
with
a
sensitivity
of
0.05
ppm.
No
detectable
residues
were
found
in
milk
from
the
0.5
g
feeding
level.
At
the
higher
feeding
levels,
milk
residues
ranged
from
0.05­
0.4
ppm.
Residues
in
milk
declined
to
nondetectable
levels
after
withdrawal
periods
of
5­
10
days.

In
the
second
study,
three
groups
of
four
lactating
dairy
cows
each
were
fed
0.1,
0.5,
and
1.0
g/
day
of
tridemorph
for
15­
16
days.
Milk
from
the
highest
dose
level
was
sampled
daily
and
milk
from
the
intermediate
level
was
sampled
on
feeding
days
3,
5,
6,
7,
9,
12,
and
15.
The
animals
were
not
slaughtered.
Tridemorph
residues
in
milk
reached
a
plateau
after
7
days
of
feeding.
Maximum
residues
from
the
1.0
g/
day
feeding
level
were
0.13
ppm.
Residues
declined
slowly
after
tridemorph
was
withdrawn
from
the
diet
and
reached
nondetectable
levels
after
7
days.
The
feeding
at
0.5
g/
day
resulted
in
trace
residues
of
about
0.01
ppm
in
milk.
Milk
from
the
0.1
g/
day
feeding
level
was
not
analyzed
(
R.
J.
Hummel,
2/
25/
76).

As
there
are
no
tolerances
for
livestock
feed
the
proposed
use
will
be
Category
3
of
Section
180.6(
a)
with
respect
to
secondary
residues
in
meat,
milk,
poultry
and
eggs.

860.1500
Crop
Field
Trials
Residue
data
were
submitted
from
three
plantations
in
Costa
Rica.
In
one
study,
bananas
were
sampled
from
1
hour
to
20
days
after
the
last
of
10
to
20
applications
of
tridemorph
at
a
rate
of
0.33
lb
ai/
A
(
0.83x
maximum
proposed
rate).
In
a
second
study,
bananas
were
sampled
1
to
20
days
after
the
last
of
11
to
19
applications
of
tridemorph
at
the
maximum
proposed
rate.
The
samples
were
shipped
to
Germany,
four
by
air
and
the
remainder
by
sea,
and
analyzed
immediately
upon
arrival.
The
time
from
the
last
application
to
analysis
varied
from
5
to
50
days.
No
detectable
residues
of
tridemorph
(<
0.05
ppm)
were
found
in
either
the
peels
or
pulp.
In
both
of
these
studies,
fruit
were
protected
by
bagging
in
polyethylene
(
R.
J.
Hummel,
2/
25/
76).

In
the
third
study,
bananas
were
sampled
4
to
18
days
after
the
last
of
11
to
21
treatments
of
tridemorph
at
0.83x
the
maximum
proposed
rate
and
shipped
by
air
to
the
U.
S.
for
analysis.
Tridemorph
residues
ranged
from
nondetectable
(<
0.01
ppm)
to
0.01
ppm
in
the
pulp
and
from
<
0.01
to
0.1
ppm
in
the
peels.
It
was
not
specified
whether
the
bananas
in
this
study
were
protected
with
polyethylene
bags
(
R.
J.
Hummel,
2/
25/
76).
The
petitioner
submitted
clarification
that
the
bananas
were,
in
fact,
protected
with
polyethylene
bags
and
agreed
to
the
following
label
restriction:
"
Do
not
apply
Calixin
to
bananas
grown
for
the
U.
S.
market
unless
they
are
to
be
bagged
on
the
plant
according
to
usual
and
common
practice"
(
R.
J.
Hummel,
6/
24/
76).

Additional
residue
data,
presumably
for
bagged
bananas,
were
subsequently
subsquently
submitted
and
reviewed
in
the
6/
24/
76
EPA
memo
from
R.
J.
Hummel.
Bananas
were
harvested
Tridemorph
Summary
of
Analytical
Chemistry
and
Residue
Data
Barcode:
D322129
14
of
18
from
plants
which
had
received
19­
21
application
of
tridemorph
at
the
maximum
proposed
rate
over
a
2
year
period.
Samples
were
shipped
to
Germany
for
analysis
(
using
the
revised
method).
No
detectable
residues
(<
0.05
ppm)
of
tridemorph
or
DMM
were
found
in
either
peel
or
pulp.
The
location
of
the
trial
was
not
reported
in
the
EPA
memo.

At
the
time
the
import
tolerance
for
tridemorph
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.
Based
on
this
new
guidance,
for
import
tolerances
in
the
U.
S.
for
bananas,
12
field
trials
are
required.
The
12
field
trials
should
be
split
between
Columbia
(
2),
Ecuador
(
3),
Honduras
(
2),
and
Guatemala
(
2).

In
12
field
trials
(
MRID
46482101)
conducted
during
2002
in
Columbia
(
2
tests),
Guatemala
(
1
test),
Costa
Rica
(
2
tests),
Mexico
(
1
test),
Ecuador
(
2
tests),
Honduras
(
2
tests),
and
Martinique
(
2
tests),
epoxiconazole
(
EC)
and
tridemorph
(
OL)
were
applied
to
bananas
as
multiple
foliar
applications.
At
each
test
site,
a
single
plot
of
bananas,
containing
both
bagged
and
unbagged
fruit
clusters,
received
10
foliar
applications
of
tridemorph
(
860
g/
L
OL)
at
0.338­
0.518
kg
ai/
ha/
application
for
a
total
of
4.16­
4.46
kg
ai/
ha/
season.
Applications
were
made
beginning
­

4­
5
months
prior
to
harvest,
at
retreatment
intervals
(
RTIs)
of
9­
14
days,
except
in
one
test
in
Costa
Rica
(
RTI
=
13­
39
days).
All
applications
were
made
using
ground
equipment;
however,
except
in
Martinique,
the
ground
applications
were
made
above
the
plant
canopy
to
simulate
aerial
application.
In
Martinique,
the
ground
applications
were
made
to
the
underside
of
the
canopy,
as
is
typical
for
this
region.
All
applications
were
made
in
50­
100%
spray
oil,
as
per
local
practices,
along
with
an
emulsifier
if
necessary.
The
final
six
applications
in
each
test
included
epoxiconazole
(
75
g/
L
EC)
in
the
tank
mix
at
a
rate
of
0.096­
0.106
kg
ai/
ha/
application
for
a
total
of
0.59­
0.62
kg
ai/
ha/
season.
The
initial
sprays
including
epoxiconazole
were
made
­

70
days
prior
to
harvest.

A
single
control
and
treated
sample
of
bagged
and
unbagged
whole
fruits
were
collected
from
each
test
and
stored
at
ambient
temperatures
for
up
to
7
days
prior
to
being
placed
in
frozen
storage.
Additional
samples
were
collected
from
two
sites
(
Costa
Rica
and
Equador)
at
3,
5,
7,
Tridemorph
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of
Analytical
Chemistry
and
Residue
Data
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D322129
15
of
18
and
10
DAT
to
examine
residue
decline.
Subsamples
of
banana
peel
and
pulp
were
also
obtained
from
each
sample.
Samples
were
stored
frozen
from
collection
to
analysis
for
up
to
12
months,
an
interval
supported
by
available
stability
data.

Residues
of
tridemorph
in
the
main
tests
were
<
0.05
ppm
(<
LOQ)
in/
on
all
samples
of
bagged
whole
bananas
(
n=
12)
harvested
at
0
DAT
and
in
all
associated
subsamples
of
pulp.
For
unbagged
fruit
samples
harvested
at
0­
DAT,
residues
of
tridemorph
were
<
0.05
ppm
in/
on
7
out
of
12
samples
of
whole
fruit;
residues
in/
on
the
remaining
5
samples
were
0.054­
0.628
ppm.
In
pulp
from
unbagged
fruits,
residues
were
<
0.05
ppm
in/
on
11
subsamples
and
0.066
ppm
in
one
subsample.
Average
tridemorph
resides
were
0.114
and
0.025
ppm
in/
on
unbagged
and
bagged
samples
of
whole
bananas
(
RAC),
respectively,
and
0.028
and
0.025
ppm
in
pulp
samples
from
unbagged
and
bagged
fruits.

The
local
cultural
practices
had
a
substantial
impact
on
residue
levels
as
residues
of
tridemorph
were
highest
in
samples
from
the
two
field
trials
conducted
in
Martinique,
which
used
applications
in
100%
spray
oil
to
the
underside
of
the
canopy.
For
these
two
tests,
residues
of
tridemorph
were
0.066­
0.085
ppm
in/
on
bagged
fruits
and
0.638­
0.907
ppm
in/
on
unbagged
fruits.

It
should
be
noted
that
the
crop
field
trials
were
conducted
prior
to
the
issuance
of
a
guidance
document
by
NAFTA
countries
on
the
data
requirements
for
import
tolerances.
Although
the
distribution
of
the
banana
field
trials
does
not
exactly
match
the
distribution
recommended
by
the
Agency,
the
12
field
trails
conducted
at
1x
during
2002
in
Columbia
(
2
tests),
Guatemala
(
1
test),
Costa
Rica
(
2
tests),
Mexico
(
1
test),
Ecuador
(
2
tests),
Honduras
(
2
tests),
and
Martinique
(
2
tests)
are
adequate.

Based
on
these
data,
the
established
tolerance
of
0.1
ppm
in/
on
banana
must
be
increased
to
1.0
ppm.

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
As
of
8/
31/
04,
an
analytical
reference
standard
for
tridemorph
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
(
40
CFR
180.41).

860.1900
Field
Accumulation
in
Rotational
Crops
Rotational
crop
studies
are
not
required
for
uses
of
pesticides
on
bananas
(
40
CFR
180.41).
Tridemorph
Summary
of
Analytical
Chemistry
and
Residue
Data
Barcode:
D322129
16
of
18
TOLERANCE
REASSESSMENT
SUMMARY
Tolerance
Reassessment
for
Tridemorph
The
tolerance
for
residues
of
tridemorph
in/
on
plant
commodities
is
expressed
in
terms
of
residues
of
tridemorph
per
se
(
2,6­
dimethyl­
4­
tridecylmorpholine).
A
summary
of
the
tridemorph
tolerance
reassessment
for
bananas
is
presented
in
Table
6.

Tolerances
Listed
Under
40
CFR
§
180.372:

A
tolerance
has
been
established
under
40
CFR
§
180.372
for
residues
of
tridemorph
in
or
on
bananas
imported
into
the
U.
S
at
0.1
ppm.
New
residue
data
indicates
the
established
tolerance
must
be
increased
to
1.0
ppm.
Additionally,
storage
stability
and
multiresidue
method
data
are
required.

Since
the
tolerance
for
tridemorph
is
an
import
tolerance,
it
should
be
footnoted
to
indicate
that
there
are
no
U.
S.
registrations
for
tridemorph.

TABLE
6.
Tolerance
Summary
for
Tridemorph
40
CFR
§
180.372
Commodity
Established/
Proposed
Tolerance
(
ppm)
Recommended
Tolerance
(
ppm)
1
Comments
/(
correct
commodity
definition)

Bananas
0.1
(
established)
1.0
The
tolerance
should
be
footnoted
to
indicate
that
there
are
no
U.
S.
registrations
associated
with
tridemorph./
banana
1
The
new
NAFTA
guidance
requires
12
field
trial
studies
for
establishing
tolerances
for
bananas.
The
current
tolerance
was
determined
using
only
4
studies.
The
established
tolerance
must
be
increased
based
on
newly
submitted
residue
data.

Codex/
International
Harmonization
There
are
no
Codex
maximum
residue
limits
(
MRLs)
for
tridemorph
listed
in
the
FAOSTAT
database;
therefore,
no
questions
of
compatibility
with
U.
S.
tolerances
exist.

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
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)
Tridemorph
Summary
of
Analytical
Chemistry
and
Residue
Data
Barcode:
D322129
17
of
18
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)

Study
Citations
40711
Beutel,
P.;
Otto,
S.
(
1976)
A
Study
Regarding
the
Formation
of
N­
Nitroso­
2,6­
dimethylmorpholine:
Report
No.
1362.
Includes
method
entitled:
Analysis
method
for
the
determination
of
N­
Nitroso
DMM
in
bananas.
(
Unpublished
study
including
published
data,
received
Aug
30,
1977
under
6E1670;
submitted
by
BASF
Wyandotte
Corp.,
Wyandotte,
Mich.;
CDL:
096339­
A)

67847
BASF
India,
Limited
(
19??)
^(
R)
ICalixin.
Bombay,
India:
BASF.
(
Technical
information,
plant
protection;
also~
In~
unpublished
submission
received
Nov
12,
1980
under
1H5281;
submitted
by
BASF
Wyandotte
Corp.,
Parsippany,
N.
J.;
CDL:
243711­
A)

135381
BASF
Wyandotte
Chemical
Corp.
(
1975)
Residue
Studies
of
Tridemorph
and
Its
Metabolite
2,6­
Dimethylmorpholine
in
Peel
and
Pulp
of
Calixin
Treated
Bananas.
(
Compilation;
unpublished
study
received
Apr
21,
1976
under
6E1670;
CDL:
098094­
A)

151337
BASF
AG
Research
Station.
(
1975)
(
Metabolism
amd
Residue
Methods
and
Analysis
for
Tridemorph
Fungicide).
Unpublished
compila­
tion.
185
p.

46482101
Johnston,
R.
(
2004)
Magnitude
of
Tridemorph
and
Epoxiconazole
Residues
in
bananas
for
Import
Tolerance.
Project
N:
2003/
5000383,
104861,
2002101.
Unpublished
study
prepared
by
BASF
Agro
Research
and
University
od
Costa
Rica
and
Agros
Consultoria
Agricola.
169
p.

46574902
Kerl,
W.
(
2003)
Method
for
the
Determination
of
Tridemorph
(
Reg.
No.
16291)
and
Epoxiconazole
(
Reg.
No.
205259)
in
Plant
Matrices.
Project
Number:
2004/
1000757,
529/
0.
Unpublished
study
prepared
by
BASF
Ag
Research
Station
(
Basf
Aktieng).
21
p.

46574903
Schulz,
H.
(
2003)
Determination
of
Tridemorph
(
Reg.
No.
16291)
and
Epoxiconazole
(
Reg.
No.
205259)
in
Bananas
­
Independent
Laboratory
Validation
of
the
BASF
Method
529/
0:
Final
Report.
Project
Number:
104855,
IF/
03/
00079588,
2003/
1001281.
Unpublished
study
prepared
by
Institut
Fresenius
Chemische
und
Biologische.
32
p.
Tridemorph
Summary
of
Analytical
Chemistry
and
Residue
Data
Barcode:
D322129
18
of
18
Agency
Memoranda
Citations.

Date
DP
Barcode
CB
No.
ID
Number
From
To
MRID
Nos.
Subject
10/
20/
75
 
 
 
R.
Ney
 
 
EEE
Branch
Review
on
tridemorph.

1/
8/
76
 
 
PP#
6E1670
K.
T.
Zee
J.
Cummings
 
PP#
6E1670.
Tridemorph
method
trial.

2/
25/
76
 
 
PP#
6E1670
R.
J.
Hummel
J.
Lee
and
Toxicology
Branch
 
PP#
6E1670.
Tridemorph
on
bananas.

Evaluation
of
Analytical
Methods
and
Residue
Data.

*
5/
11/
76
R.
D.
Coberly
Personal
Communication
6/
24/
76
 
 
PP#
6E1670
R.
J.
Hummel
J.
Lee
and
Toxicology
Branch
 
PP#
6E1670.
Tridemorph
on
bananas.

Amendment
of
4/
20/
76.

10/
25/
77
PP#
6E1670
R.
J.
Hummel
J.
Lee
and
Toxicology
Branch
 
Tridemorph
on
bananas.
Amendment
of
8/
30/
77.

10/
20/
78
PP#
6E1670/

R162
U.
S.
EPA
Office
of
Pesticide
Programs
Part
180­
Tolerances
and
Exemptions
from
Tolerances
for
Pesticide
Chemicals
in
or
on
Raw
Agricultural
Commodities:
2, 
Dimethyl­
4­

Tridecylmorpholine
(
Final
Rule)

4/
13/
82
 
 
PP#
1H5281
G.
Ghali
H.
Jacoby
 
Tridemorph
on
dried
tea.
PP#
1H5281
(
Acc.
No.
243711,
Caswell
No.
386).

9/
8/
83
 
 
ID#
7969­
Q
N.
Dodd
H.
Jacoby
 
ID#
7969­
Q.
Amended
registration
for
tridemorph
on
bananas.

11/
2/
05
D302111,
D302111A
G.
Otakie
HED
46482101,
46574902,

46574903
Tridemorph
residues
in/
on
bananas
for
import
tolerance
and
analytical
method
and
ILV.

xx/
xx/
05
D267877,

D318715
A.
Acierto
HED
46482101,
46574902,

46574903
PP#
7E4885
Epoxiconazole
residues
in/
on
bananas
and
analytical
method
and
ILV.

*
The
personal
communication
was
documented
in
the
EPA
memo
from
R.
J.
Hummel
dated
6/
24/
76.
