Kresoxim­
Methyl
Summary
of
Analytical
Chemistry
and
Residue
Data
DP#:
328725
Page
1
of
23
UNITED
STATES
ENVIRONMENTAL
PROTECTION
AGENCY
WASHINGTON,
D.
C.
20460
OFFICE
OF
PREVENTION,
PESTICIDES
AND
TOXIC
SUBSTANCES
MEMORANDUM
Date:
26­
MAY­
2006
Subject:
Kresoxim­
Methyl.
Petition
for
the
Establishment
of
a
Crop
Group
Tolerance
on
Cucurbit
Vegetables.
Summary
of
Analytical
Chemistry
and
Residue
Data.
PP#
3E6594.

DP
#:
328725
Decision
#:
354442
PC
Code:
129111
MRID
Nos.:

40
CFR.
§
180.554
Chemical
Class:
Strobilurin
Fungicide;
Quinone
Outside
Inhibitor
(
QoI)
Fungicide
45101401,
45101402,
45101403,
45101404,
and
45939305
From:
George
F.
Kramer,
Ph.
D.,
Chemist
Registration
Branch
1
(
RAB1)
Health
Effects
Division
(
HED;
7509C)

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

To:
Barbara
Madden/
Dan
Rosenblatt,
PM
Team
05
Registration
Division
(
RD;
7505C)

This
document
was
originally
prepared
under
contract
by
Dynamac
Corporation
(
2275
Research
Blvd,
Suite
300;
Rockville,
MD
20850;
submitted
02/
09/
2006).
The
document
has
been
reviewed
by
HED
and
revised
to
reflect
current
Office
of
Pesticide
Programs
(
OPP)
policies.

Executive
Summary
The
Interregional
Research
Project
No.
4
(
IR­
4),
on
behalf
of
the
Agricultural
Experiment
Stations
of
AZ,
CA,
MI,
NC,
NY,
OK,
OR,
SC,
TN,
and
WI,
has
submitted
a
petition
for
an
amended
Section
3
registration
of
Sovran
®
Fungicide
(
EPA
Reg.
No.
7969­
154),
a
50%
kresoxim­
methyl
dry­
flowable
(
DF)
formulation,
for
use
on
cucurbit
vegetables.
The
petitioner
requests
the
establishment
of
a
permanent
tolerance
for
the
combined
residues
of
kresoxim­
methyl
[
methyl
(
 E)­
 ­(
methoxyimino)­
2­[(
2­
methylphenoxy)
methyl]
benzeneacetate]
and
its
metabolites
BF
490­
2
[
2­[
o­(
o­
hydroxymethylphenoxymethyl)
phenyl]­
2­(
methoxyimino)
acetic
acid]
and
BF
490­
9
[
2­[
o­(
p­
hydroxymethylphenoxymethyl)
phenyl]­
2­(
methoxyimino)
acetic
acid]
as
follows:
Crop
Group
9,
Cucurbit
Vegetables
Group
 .   
0.5
ppm
Kresoxim­
Methyl
Summary
of
Analytical
Chemistry
and
Residue
Data
DP#:
328725
Page
2
of
23
Kresoxim­
methyl
belongs
to
the
Quinone
Outside
Inhibitor
(
QoI)
class
of
fungicides.
It
inhibits
mitochondrial
respiration
by
blocking
electron
transfer
at
the
bc1
complex
in
fungi.
The
protective
effect
is
due
to
the
inhibition
of
both
spore
germination
and
host
infection.
The
curative
and
eradicative
effects
are
the
result
of
kresoxim­
methyl's
inhibition
of
mycelial
growth
and
sporulation.
This
is
the
second
food­
use
application
for
kresoxim­
methyl.
The
first
food­
use
registration
for
this
active
ingredient
(
a.
i.)
on
pome
fruits,
grapes,
and
pecans
was
conditionally
approved
through
PP#
7F04880
(
D255097;
T.
Bloem,
4/
12/
1999).

The
50%
DF
formulation
is
to
be
used
for
multiple
foliar
sprays
on
cucurbit
vegetables
for
the
control
of
powdery
mildew
and
gummy
stem
blight.
Up
to
six
foliar
treatments
may
be
made,
with
retreatment
intervals
of
7­
10
days,
at
a
maximum
single
application
rate
of
0.15
lb
ai/
A.
The
label
specifies
a
maximum
seasonal
rate
of
0.9
lb
ai/
A,
and
a
preharvest
interval
(
PHI)
of
0
days.

The
nature
of
the
residues
in
pome
fruits,
grapes
and
wheat
is
adequately
understood.
The
major
metabolic
pathway
for
kresoxim­
methyl
in
the
above
crops
is
the
isomerization
to
its
Z­
isomer
(
a
minor
component)
or
hydrolysis
of
the
ester
to
the
acid
(
BF
490­
1).
This
acid
metabolite
oxidizes
at
one
of
the
three
positions
on
the
cresyl
ring
to
yield
BF
490­
2,
BF
490­
9,
and/
or
BF
490­
15.
All
of
the
hydroxylated
metabolites
undergo
conjugation
with
glucose.
There
is
no
apparent
cleavage
of
the
two
rings.

The
Metabolism
Assessment
Review
Committee
(
MARC)
previously
determined
that
the
available
plant
metabolism
studies
are
sufficient
for
the
registration
of
kresoxim­
methyl
on
pome
fruits,
grapes,
pecans,
and
related
crops
(
fruit
or
fruiting
vegetables).
The
MARC
also
determined
that
the
tolerance
expression
for
kresoxim­
methyl
in/
on
pome
fruits,
grapes
and
pecans
will
include
kresoxim­
methyl,
BF
490­
1,
BF
490­
2
(
free
and
glucose
conjugated)
and
BF
490­
9
(
free
and
glucose
conjugated).
The
kresoxim­
methyl
tolerances
established
in
40
CFR
§
180.554
for
apple
pomace,
pome
fruit,
grape,
raisin,
and
pecans
are
expressed
as
above.
It
is
noted
that
the
metabolite
BF
490­
1
is
included
in
the
tolerance
expression
because
the
analytical
methods
do
not
distinguish
between
kresoxim­
methyl
and
BF
490­
1.

The
nature
of
the
residues
in
rotational
crops
is
adequate
pending
submission
of
supporting
sample
storage
stability
information/
data.
In
the
submitted
confined
rotational
crop
study,
total
radioactive
residues
(
TRR)
accumulated
at
 
0.01
ppm
in
all
rotated
crops
(
radish,
Swiss
chard,
and
sorghum)
planted
14/
28,
91,
or
210/
245
days
following
four
applications
of
[
14C]
kresoximmethyl
for
a
total
rate
of
1.2
lb
ai/
A
(
1.3x).
The
parent,
kresoxim­
methyl,
was
not
detected
in/
on
any
rotational
crop
commodity
at
any
plantback
interval
(
PBI).
The
major
residue
components
identified
in
rotational
crop
commodities
were
the
glucosides
of
490
M2
and
490
M9.
These
conjugated
metabolites,
490
M2
and
490
M9,
are
converted
to
their
unconjugated
metabolites
BF
490­
2
and
BF
490­
9
following
enzyme
hydrolysis.
The
metabolic
pathway
of
kresoxim­
methyl
in
rotational
crops
involves
the
initial
cleavage
of
the
acid
ester
to
the
free
acid
(
490
M1),
the
oxidation
of
the
A
ring
to
form
hydroxylated
products
(
490
M2
and
490
M9),
the
conjugation
of
these
hydroxylated
products
to
glucose
(
490­
B
and
490­
C),
and
the
final
incorporation
of
these
metabolites
into
natural
products.

The
requirements
for
livestock
metabolism
data,
analytical
enforcement
methodology
for
livestock
commodities,
storage
stability
data
for
livestock
commodities,
and
magnitude
of
the
residue
data
in
meat,
milk,
poultry
and
eggs
are
not
relevant
to
this
petition
because
there
are
no
feedstuffs
Kresoxim­
Methyl
Summary
of
Analytical
Chemistry
and
Residue
Data
DP#:
328725
Page
3
of
23
associated
with
the
proposed
use
on
cucurbit
vegetables.

There
is
an
adequate
analytical
methodology
for
tolerance
enforcement
of
regulated
residues
in/
on
plant
commodities.
BASF
Methods
350/
3­
US
and
D9611A
are
high­
performance
liquid
chromatography
(
HPLC)/
column­
switching
methods
with
ultraviolet
(
UV)
detection
(
270
nm)
which
have
been
determined
to
meet
Agency
guidelines
for
the
enforcement
of
kresoxim­
methyl
tolerances
on
plant
commodities.
BASF
Method
350/
3­
US
converts
glucose
conjugates
of
BF
490­
B
and
BF
490­
C
to
their
unconjugated
forms
BF
490­
2
and
BF
490­
9,
respectively,
following
enzyme
hydrolysis.
The
parent,
kresoxim­
methyl,
is
converted
to
the
acid
metabolite
BF
490­
1
following
enzymatic
cleavage
and
base
hydrolysis.
The
metabolite
BF
490­
1
is
measured
as
kresoxim­
methyl
equivalents.

The
methods
have
been
forwarded
to
FDA
for
publication
as
Roman
numeral
methods
in
the
Pesticide
Analytical
Manual
(
PAM)
Volume
II.
BASF
Method
350/
3­
US
will
be
designated
as
Method
I
and
has
been
determined
to
be
applicable
for
pome
fruits,
apple
pomace,
grapes,
and
raisins;
this
method
will
also
be
suitable
for
cucurbit
vegetables.
BASF
Method
D9611A
will
be
designated
as
Method
II
and
is
applicable
for
pecans.
The
limit
of
quantitation
(
LOQ)
is
0.05
ppm
for
each
analyte
(
BF
490­
1,
BF
490­
2,
and
BF
490­
9).
The
limit
of
detection
(
LOD)
is
described
as
about
0.025
ppm
for
each
analyte.

Samples
collected
from
the
submitted
field
trials,
storage
stability,
and
field
rotational
crop
studies
were
analyzed
for
residues
of
kresoxim­
methyl
and
its
metabolites
BF
490­
2
and
BF
490­
9
using
BASF
Method
350/
3­
US
or
a
slightly
modified
version
of
the
method.
Concurrent
method
recoveries
were
well
within
the
acceptable
range
of
70­
120%.

Adequate
storage
stability
data
are
available
to
support
the
storage
conditions
and
intervals
of
crop
commodity
samples
collected
from
cucurbit
field
trials
as
well
as
from
the
limited
field
rotational
crop
study.
There
are
no
storage
stability
issues
or
corrections
that
may
need
to
be
applied
to
the
various
residue
studies.

Adequate
field
trial
data
are
available
for
cantaloupes,
cucumbers,
and
summer
squash,
which
are
the
representative
crops
of
cucurbit
vegetables
(
Crop
group
9).
The
maximum
combined
residues
of
kresoxim­
methyl
and
its
metabolites
BF
490­
2
and
BF
490­
9
in/
on
cucurbit
vegetables
harvested
0
days
following
the
last
of
six
broadcast
foliar
applications
of
the
50%
DF
formulation
for
a
total
seasonal
rate
of
~
1.0
lb
ai/
A
(~
1.1x)
were
<
0.320
ppm
in/
on
cantaloupes,
<
0.220
ppm
in/
on
cucumber,
and
<
0.340
ppm
in/
on
summer
squash.
The
parent
accounted
for
the
majority
of
the
combined
residues;
maximum
individual
residues
of
kresoxim­
methyl
in/
on
treated
samples
were
0.220
ppm
for
cantaloupes,
0.120
ppm
for
cucumbers,
and
0.240
ppm
for
squash.
Individual
residues
of
metabolites
BF
490­
2
and
BF
490­
9
were
each
below
the
method
LOQ
(<
0.05
ppm)
in/
on
all
treated
samples
collected
at
a
0­
day
PHI.
Based
on
these
data,
the
recommended
tolerance
level
for
kresoxim­
methyl
on
"
Vegetable,
cucurbit,
group
9"
is
0.40
ppm.

An
acceptable
limited
field
rotational
crop
study
with
kresoxim­
methyl
is
available.
Representative
rotational
crops
of
cabbage
(
leafy
vegetable),
radish
(
root
vegetable),
and
wheat
(
cereal
grain)
were
planted
at
intervals
of
~
14,
30,
and
45
days
after
the
primary
crop
(
cucumbers)
was
treated
at
~
1.2x
and
harvested
at
maturity.
Only
residues
of
the
glycoside
metabolites
(
BF
490­
2
and
BF
490­
9)
were
measured
in
this
limited
study
since
these
glycoside
Kresoxim­
Methyl
Summary
of
Analytical
Chemistry
and
Residue
Data
DP#:
328725
Page
4
of
23
metabolites
were
the
predominant
residues
identified
in
the
confined
rotational
crop
study.
The
results
indicate
that
at
a
PBI
of
14
days,
residues
of
BF
490­
2
and
BF
490­
9
were
each
below
the
LOQ
(<
0.05
ppm)
in/
on
cabbage
(
with
and
without
wrapper
leaves),
radish
roots
and
tops,
and
wheat
forage,
hay,
straw,
and
grain.
Because
residues
were
below
the
LOQ
in
all
samples
of
rotated
crop
commodities
from
the
14­
day
PBI,
samples
from
later
PBIs
were
not
analyzed.
Based
on
these
data,
HED
concludes
that
tolerances
for
rotational
crop
commodities
are
not
required
for
the
purpose
of
this
petition
provided
the
label
for
Sovran
®
Fungicide
(
EPA
Reg.
No.
7969­
154)
is
amended
to
specify
a
PBI
of
14
days.

Analytical
standards
for
kresoxim­
methyl
are
currently
available
in
the
National
Pesticide
Standards
Repository.
However,
standards
for
the
regulated
metabolites
(
BF
490­
1,
BF
490­
2,
and
BF
490­
9)
are
not
available
and
should
be
submitted
to
the
Repository.

Regulatory
Recommendations
and
Residue
Chemistry
Deficiencies
Provided
revised
Sections
B
and
F
are
submitted,
HED
concludes
there
are
no
residue
chemistry
data
requirements
that
would
preclude
establishing
conditional
registrations
and
permanent
tolerances
for
residues
of
kresoxim­
methyl
and
its
metabolites
BF
490­
2
and
BF
490­
9
in/
on
"
Vegetable,
cucurbit,
group
9"
at
0.40
ppm.
Registration
should
be
made
conditional
pending
resolutions
of
deficiencies
regarding
the
confined
rotational
crop
study
and
the
submission
of
reference
analytical
standards
for
kresoxim­
methyl
metabolites.

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

860.1200
Directions
for
Use
°
The
label
for
Sovran
®
Fungicide
(
EPA
Reg.
No.
7969­
154)
should
be
amended
to
specify
a
PBI
interval
of
14
days.

860.1850
Confined
Accumulation
in
Rotational
Crops
°
To
upgrade
the
submitted
confined
rotational
crop
study
(
MRID
45101404),
the
petitioner
should
provide
dates
of
analysis
for
all
sample
extracts
and
hydrolysates.
In
addition,
if
final
analyses
of
samples
and
extracts
were
not
completed
within
18
months
of
sample
collection
for
any
rotated
crop,
the
petitioner
should
provide
data
demonstrating
that
the
metabolite
profile
in
the
rotated
crop
was
stable
during
the
storage
interval
of
the
study.

860.1550
Proposed
Tolerances
°
The
petitioner
should
submit
a
revised
Section
F
to
reflect
all
the
residues
of
concern
[
kresoxim­
methyl,
BF
490­
1,
BF
490­
2
(
free
and
glucose
conjugated)
and
BF
490­
9
(
free
and
glucose
conjugated)]
in
the
tolerance
expression
as
specified
in
40
CFR
§
180.554(
a)(
1):
"
for
the
combined
residues
of
the
fungicide
kresoxim­
methyl
(
methyl
(
E)­
2­[
2­(
2­
methylphenoxy)­
methyl]
phenyl­
2­(
methoxyimido)
acetate)
and
its
metabolites
as
follows:
(
E)­
2­[
2­(
2­
methylphenoxy)
methyl]­
phenyl­
2­(
methoxyimido)
acetic
acid;
(
E)­
2­[
2­(
2­
hydroxymethylphenoxy)
methyl]­
phenyl­
2­(
methoxyimido)
acetic
acid
(
free
and
glucose
conjugated);
and
(
E)­
2­[
2­(
4­
hydroxy­
2­
methylphenoxy)­
methyl]
phenyl­
2­(
methoxyimido)
acetic
acid
(
free
and
glucose
conjugated)."
In
addition,
the
petitioner
should
revise
commodity
Kresoxim­
Methyl
Summary
of
Analytical
Chemistry
and
Residue
Data
DP#:
328725
Page
5
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23
definition
from
"
Crop
Group
9,
Cucurbit
Vegetables
Group"
to
"
Vegetable,
cucurbit,
group
9."

860.1650
Submittal
of
Analytical
Reference
Standards
°
Analytical
standards
for
kresoxim­
methyl
metabolites
(
BF
490­
1,
BF
490­
2,
and
BF
490­
9)
are
required.
The
reference
standards
should
be
sent
to
the
Analytical
Chemistry
Lab,
which
is
located
at
Fort
Meade,
to
the
attention
of
either
Theresa
Cole
or
Frederic
Siegelman
at
the
following
address:

USEPA
National
Pesticide
Standards
Repository/
Analytical
Chemistry
Branch/
OPP
701
Mapes
Road
Fort
George
G.
Meade,
MD
20755­
5350
(
Note
that
the
mail
will
be
returned
if
the
extended
zip
code
is
not
used.)

Background
The
nomenclature
and
chemical
structure
of
kresoxim­
methyl
are
listed
below
in
Table
1.
The
physicochemical
properties
of
kresoxim­
methyl
are
listed
in
Table
2.
The
chemical
names
and
structures
of
kresoxim­
methyl
and
its
transformation
products
identified
from
the
submitted
confined
rotational
crop
study
are
presented
in
Appendix
I.

TABLE
1.
Kresoxim­
Methyl
Nomenclature.

Compound
O
CH
3
N
O
CH
3
O
O
C
H
3
Common
name
Kresoxim­
methyl
Company
experimental
name
BAS
490
F
IUPAC
name
methyl
(
E)­
2­
methoxyimino­
2­[
2­(
o­
tolyloxymethyl)
phenyl]
acetate
CAS
name
methyl
(
 E)­
 ­(
methoxyimino)­
2­[(
2­
methylphenoxy)
methyl]
benzeneacetate
CAS
registry
number
143390­
89­
0
End­
use
product
(
EP)
Sovran
®
Fungicide
(
EPA
Reg.
No.
7969­
154)

TABLE
2.
Physicochemical
Properties
of
the
Technical
Grade
Kresoxim­
Methyl.

Parameter
Value
Reference
Melting
range
PAI:
97.2­
101.7
°
C
TGAI:
98­
100
°
C
PMRA
Document
PRDD2003­
05
pH
5.8
USEPA;
Pesticide
Fact
Sheet
for
Kresoxim­
Methyl
(
143390­
89­
0)

Density
PAI:
1.258
g/
cm3
at
20
°
C
PMRA
Document
PRDD2003­
05
Water
solubility
PAI:
2.00
±
0.08
mg/
L
(
20
°
C)
PMRA
Document
PRDD2003­
05
Kresoxim­
Methyl
Summary
of
Analytical
Chemistry
and
Residue
Data
DP#:
328725
Page
6
of
23
TABLE
2.
Physicochemical
Properties
of
the
Technical
Grade
Kresoxim­
Methyl.

Parameter
Value
Reference
Solvent
solubility
(
g/
100
mL
@
20
°
C)
n­
heptane
0.172
toluene
11.1
dichloromethane
93.9
methanol
1.46
acetone
2.17
ethyl
acetate
12.3
acetonitrile
16.6
i­
propanol
0.480
PMRA
Document
PRDD2003­
05
Vapor
pressure
2.3
x
10­
6
Pa
at
20
°
C
PMRA
Document
PRDD2003­
05
Dissociation
constant,
pKa
No
pKa
value
at
pH
2­
12
PMRA
Document
PRDD2003­
05
Octanol/
water
partition
coefficient,
Log(
KOW)
3.4
±
0.02
PMRA
Document
PRDD2003­
05
UV/
visible
absorption
spectrum
at
26
°
C
 max
at
204
nm,
no
absorption
at
 >
350
nm
PMRA
Document
PRDD2003­
05
860.1200
Directions
for
Use
Table
3.
Summary
of
Proposed
End­
Use
Products.

Trade
Name
EPA
Reg.
No.
ai
(%
of
formulation)
Formulation
Type
Target
Crops
Target
Pests
Label
Date
Sovran
®

Fungicide
7969­
154
50%
DF
Cucurbit
vegetables
Powdery
mildew
and
gummy
stem
blight
Not
specified
Table
4.
Summary
of
Proposed
Directions
for
Use
of
Kresoxim­
methyl.

Trade
Name
Application
Timing
Application
Rate
(
lb
ai/
A)
Max.
No.
Applic.
per
Season
RTI1
(
days)
Max.
Seasonal
Applic.
Rate
(
lb
ai/
A)
PHI
(
days)
Use
Directions
and
other
Limitations
Cucurbit
Vegetables:
EPA
Crop
Group
9:
Citron
melon,
muskmelon;
watermelon;
Chayote;
Chinese
waxgourd;
cucumber;
gherkin;
gourd,
edible;
Momordica
spp.;
pumpkin;
squash,
summer;
squash,
winter
Sovran
®

fungicide
Foliar
spray
0.1­
0.15
6
7­
10
0.9
0
Applications
may
be
made
using
ground
equipment.
Application
through
any
type
of
irrigation
system
is
prohibited.
1
RTI
=
Retreatment
interval
Conclusions.
The
submitted
product
label
for
Sovran
®
Fungicide
(
EPA
Reg.
No.
7969­
154)
is
adequate
to
allow
evaluation
of
the
residue
data
relative
to
the
proposed
use
on
cucurbit
vegetables.
However,
based
on
the
results
of
the
limited
field
rotational
crop
study,
the
label
should
be
amended
to
specify
a
PBI
interval
of
14
days.

860.1300
Nature
of
the
Residue
­
Plants
The
nature
of
the
residues
in
plants
is
adequately
understood
based
on
acceptable
metabolism
studies
conducted
on
pome
fruits,
grapes,
and
wheat
(
PP#
7F04880;
D255097,
4/
12/
1999,
T.
Bloem).
The
major
metabolic
pathway
for
kresoxim­
methyl
in
pome
fruits,
grapes
and
wheat
is
isomerization
to
its
Z­
isomer
(
a
minor
component)
or
hydrolysis
of
the
ester
to
the
acid
(
BF
490­
1).
This
acid
metabolite
oxidizes
at
one
of
the
three
positions
on
the
cresyl
ring
to
yield
BF
490­
2,
BF
490­
9,
and/
or
BF
490­
15.
All
of
the
hydroxylated
metabolites
undergo
conjugation
with
Kresoxim­
Methyl
Summary
of
Analytical
Chemistry
and
Residue
Data
DP#:
328725
Page
7
of
23
glucose.
There
is
no
apparent
cleavage
of
the
two
rings.

The
HED
MARC
determined
that
the
submitted
plant
metabolism
studies
are
sufficient
for
registration
of
kresoxim­
methyl
on
pome
fruits,
grapes
and
pecans
and
related
crops
(
fruit
or
fruiting
vegetables).
The
grain
metabolism
study
would
cover
registration
on
grain
crops.
If
the
petitioner
wishes
to
register
uses
on
root
crops
or
leafy
vegetables,
then
additional
plant
metabolism
studies
may
be
necessary.
The
MARC
determined
that
the
tolerance
expression
for
kresoxim­
methyl
in/
on
pome
fruits,
grapes
and
pecans
will
include
kresoxim­
methyl,
BF
490­
1,
BF
490­
2
(
free
and
glucose
conjugated)
and
BF
490­
9
(
free
and
glucose
conjugated)
(
D254643,
4/
5/
1999,
T.
Bloem).

860.1300
Nature
of
the
Residue
­
Livestock
Data
requirements
for
this
guideline
topic
are
not
relevant
to
this
petition
since
there
are
no
livestock
feedstuffs
associated
with
the
proposed
use
on
cucurbit
vegetables.

860.1340
Residue
Analytical
Methods
There
is
adequate
analytical
methodology
for
tolerance
enforcement
of
regulated
residues
in/
on
plant
commodities.
BASF
Methods
350/
3­
US
and
D9611A
are
HPLC/
column­
switching
methods
with
UV
detection
(
270
nm)
which
have
been
determined
to
meet
Agency
guidelines
for
the
enforcement
of
kresoxim­
methyl
tolerances
on
plant
commodities.
BASF
Method
350/
3­
US
converts
glucose
conjugates
of
BF
490­
B
and
BF
490­
C
to
their
unconjugated
forms
BF
490­
2
and
BF
490­
9,
respectively,
following
enzyme
hydrolysis.
The
parent,
kresoxim­
methyl,
is
converted
to
the
acid
metabolite
BF
490­
1
following
enzymatic
cleavage
and
base
hydrolysis.
The
metabolite
BF
490­
1
is
measured
as
kresoxim­
methyl
equivalents.

The
methods
have
been
forwarded
to
FDA
for
publication
as
Roman
numeral
methods
in
the
Pesticide
Analytical
Manual
(
PAM)
Volume
II.
BASF
Method
350/
3­
US
will
be
designated
as
Method
I
and
has
been
determined
to
be
applicable
for
pome
fruits,
apple
pomace,
grapes,
and
raisins;
this
method
will
also
be
suitable
for
cucurbit
vegetables.
BASF
Method
D9611A
will
be
designated
as
Method
II
and
is
applicable
for
pecans.
The
LOQ
is
0.05
ppm
for
each
analyte
(
BF
490­
1,
BF
490­
2,
and
BF
490­
9).
The
LOD
is
about
0.025
ppm
for
each
analyte.

Samples
collected
from
the
submitted
field
trials,
storage
stability,
and
field
rotational
crop
studies
were
analyzed
for
residues
of
kresoxim­
methyl
and
its
metabolites
BF
490­
2
and
BF
490­
9
using
BASF
Method
350/
3­
US
or
a
slightly
modified
version
of
the
method.
Concurrent
method
recoveries
were
well
within
the
acceptable
range
of
70­
120%.

860.1360
Multiresidue
Methods
The
data
requirements
for
multiresidue
methods
are
fulfilled.
It
was
reported
in
PP#
7F04880
(
D255097,
4/
12/
1999,
T.
Bloem)
that
acceptable
recoveries
and
standard
deviations
were
achieved
with
protocols
D,
E,
and
F
for
kresoxim­
methyl.
Recoveries
for
BF
490­
2
and
BF
490­
9
were
low
or
variable.
BF
490­
9
was
recovered
well
through
protocols
B
and
D
in
a
non­
fatty
Kresoxim­
Methyl
Summary
of
Analytical
Chemistry
and
Residue
Data
DP#:
328725
Page
8
of
23
matrix
(
grapes).
BF
490­
1
was
recovered
adequately
through
protocols
E
and
F.
No
single
protocol
recovered
all
of
the
compounds
efficiently.
Additionally,
none
of
the
protocols
incorporate
enzymatic
release
of
the
conjugated
residues.
The
Multiresidue
Methods
are
thus
not
suitable
for
enforcement
of
the
proposed
tolerances.

860.1380
Storage
Stability
45101402.
der.
doc
(
Cucumbers)
45101403.
der.
doc
(
Grapes,
Apples,
and
Processed
Apple
Commodities)

In
support
of
sample
storage
intervals
from
the
magnitude
of
the
residue
and
limited
field
rotational
studies,
BASF
Corporation
submitted
storage
stability
studies
investigating
the
recovery
of
fortified
residues
of
kresoxim­
methyl
and
its
metabolites
BF
490­
B
and
BF
490­
C
in/
on
various
plant
commodities.
These
studies
have
been
reviewed,
and
the
Executive
Summaries
from
study
DERs
are
reproduced
below.

MRID
45101402
BASF
Corporation
has
submitted
the
results
of
a
storage
stability
study
with
kresoxim­
methyl
on
cucumbers.
Untreated
samples
of
cucumber
were
fortified
with
kresoxim­
methyl
at
1.0
ppm
and
then
stored
frozen
(<­
10
°

C).
At
storage
intervals
of
0,
2,
6,
and
12
month,
subsamples
of
the
spiked
cucumbers
were
analyzed
for
residues
of
kresoxim­
methyl
using
BASF
Method
350/
3­
US,
an
HPLC
method
with
UV
detection
(
270
nm).
The
method
is
adequate
for
data
collection
based
on
acceptable
concurrent
method
recovery
data.
The
results
indicate
that
residues
of
kresoximmethyl
are
stable
(
storage
stability
recoveries
of
81­
110%)
under
frozen
storage
conditions
for
up
to
12
months
in/
on
cucumbers.

MRID
45101403
BASF
Corporation
has
submitted
the
final
results
of
a
storage
stability
study
with
kresoximmethyl
and/
or
its
metabolites
BF
490­
B
and
BF
490­
C
in/
on
grapes,
apples,
wet
apple
pomace,
and
apple
juice.
The
interim
results
of
this
study
were
previously
reported
and
reviewed
in
conjunction
with
a
previous
petition
on
apples
and
grapes
(
PP#
7F4880;
D255097,
T.
Bloem,
4/
12/
99).
Untreated
samples
of
grapes,
apples,
apple
wet
pomace,
and
apple
juice
were
fortified
with
kresoxim­
methyl
at
1.0
ppm
and
then
stored
frozen
(<­
10
°

C).
In
addition,
untreated
samples
of
grapes
and
apples
were
each
fortified
with
BF
490­
B
at
0.258­
0.393
ppm
and
with
BF
490­
C
at
0.332­
0.504
ppm;
these
samples
were
also
stored
frozen
(<­
10
°

C)
after
spiking.
At
storage
intervals
of
0,
2,
6,
12,
and
26
months,
subsamples
of
the
fortified
matrices
were
taken
for
analysis
using
BASF
Method
350/
3­
US,
an
HPLC
method
with
UV
detection
(
270
nm).
The
method
is
adequate
for
data
collection
based
on
acceptable
concurrent
method
recovery
data.
The
results
indicate
that
fortified
residues
of
kresoxim­
methyl
are
stable
under
frozen
storage
conditions
for
up
to
26
months
in/
on
grapes
and
for
12
months
in/
on
apples,
wet
apple
pomace,
and
apple
juice.
Fortified
residues
of
the
glucose
conjugate
metabolites
BF
490­
B
and
BF
490­
C
are
each
stable
for
up
to
26
months
in/
on
grapes
and
for
12
months
in/
on
apples.

Conclusions.
Adequate
storage
stability
data
for
kresoxim­
methyl
and
its
metabolites
are
available
to
support
the
storage
conditions
and
intervals
of
field
trial
samples.
The
maximum
Kresoxim­
Methyl
Summary
of
Analytical
Chemistry
and
Residue
Data
DP#:
328725
Page
9
of
23
storage
intervals
of
samples
collected
from
the
magnitude
of
the
residue
study
were
278
days
(
9.1
months)
for
cantaloupes,
295
days
(
9.7
months)
for
cucumbers,
and
314
days
(
10.3
months)
for
squash.
The
maximum
storage
intervals
of
samples
collected
from
the
limited
rotational
crop
study
were
295
days
(
9.7
months)
for
cabbage
(
with
and
without
wrapper
leaves),
344
days
(
11.3
months)
for
radish
(
roots
and
tops),
292
months
(
9.6
months)
for
wheat
forage,
194
days
(
6.4
months)
for
wheat
hay,
161
days
(
5.3
months)
for
wheat
straw
and
grain.
The
available
storage
stability
data
indicate
that:
(
i)
kresoxim­
methyl
is
stable
under
frozen
storage
conditions
in/
on
cucumbers,
apple
wet
pomace,
and
apple
juice
for
up
to
12
months;
and
(
ii)
kresoxim­
methyl
and
its
metabolites
(
BF
490­
B
and
BF
490­
C)
are
stable
under
frozen
conditions
in/
on
apples
for
up
to
12
months
and
grapes
for
up
to
26
months.
There
are
no
storage
stability
issues
or
corrections
that
may
need
to
be
applied
to
the
various
residue
studies.

860.1480
Meat,
Milk,
Poultry,
and
Eggs
Data
requirements
pertaining
to
this
guideline
topic
are
not
relevant
to
this
petition
because
there
are
no
feedstuffs
associated
with
the
proposed
use
on
cucurbit
vegetables.

860.1500
Crop
Field
Trials
45101401.
der.
doc
(
Cucurbit
Vegetables)

Table
5.
Summary
of
Residue
Data
from
Crop
Field
Trials
with
Kresoxim­
Methyl.

Residue
Levels
(
ppm)
1
Commodity
Total
Applic.
Rate
(
lb
ai/
A)
PHI
(
days)
Analyte
N
Min.
Max.
HAFT2
Median
Mean
Std.
Dev.

Kresoximmethyl
12
<
0.05
0.220
0.210
0.088
0.101
0.057
BF
490­
2
12
<
0.05
<
0.05
<
0.05
0.025
0.025
0.0
BF
490­
9
12
<
0.05
<
0.05
<
0.05
0.025
0.025
0.0
Cantaloupe
1.044­
1.0552
0
Combined
12
<
0.15
<
0.320
<
0.310
0.138
0.151
0.057
Kresoximmethyl
16
<
0.05
0.120
0.106
0.025
0.037
0.030
BF
490­
2
16
<
0.05
<
0.05
<
0.05
0.025
0.025
0.0
BF
490­
9
16
<
0.05
<
0.05
<
0.05
0.025
0.025
0.0
Cucumber
1.0462­
1.0695
0
Combined
16
<
0.15
<
0.220
<
0.206
0.075
0.087
0.030
Kresoximmethyl
10
<
0.05
0.240
0.219
0.025
0.066
0.081
BF
490­
2
10
<
0.05
<
0.05
<
0.05
0.025
0.025
0.0
BF
490­
9
10
<
0.05
<
0.05
<
0.05
0.025
0.025
0.0
Squash,
summer
1.049­
1.0742
0
Combined
10
<
0.15
<
0.340
<
0.319
0.075
0.116
0.081
1
The
LOQ
was
0.05
ppm
for
kresoxim­
methyl,
BF
490­
2,
and
BF
490­
9.
The
LOD
was
0.025
ppm
for
each
analyte.
The
minimum,
maximum,
and
HAFT
values
are
based
on
the
LOQ.
For
calculating
the
median,
mean,
and
standard
deviation,
half
the
LOQ
was
used
for
residues
reported
below
the
LOQ
in
Table
C.
3.
2
HAFT
=
Highest
Average
Field
Trial.

BASF
Corporation
has
submitted
field
trial
data
for
kresoxim­
methyl
on
the
representative
crops
(
cantaloupes,
cucumbers,
and
summer
squash)
of
the
cucurbit
vegetable
crop
group.
A
total
of
Kresoxim­
Methyl
Summary
of
Analytical
Chemistry
and
Residue
Data
DP#:
328725
Page
10
of
23
19
field
trials
were
conducted
during
the
1997
growing
season.
Six
cantaloupe
field
trials
were
conducted
in
Regions
2
(
AL;
1
trial),
5
(
MI;
1
trial),
6
(
OK;
1
trial),
and
10
(
CA;
3
trials).
Eight
cucumber
trials
were
conducted
in
Regions
2
(
GA
and
SC;
3
trials),
3
(
FL;
1
trial),
5
(
MI
and
WI;
2
trials),
6
(
TX;
1
trial),
and
10
(
CA;
1
trial).
Five
summer
squash
field
trials
were
conducted
in
Regions
1
(
PA;
1
trial),
2
(
NC;
1
trial),
3
(
FL;
1
trial),
5
(
WI;
1
trial),
and
10
(
CA;
1
trial).
The
number
and
locations
of
field
trials
are
in
accordance
with
OPPTS
Guideline
860.1500
for
cantaloupe,
cucumber,
and
summer
squash
as
the
representative
crops
of
the
cucurbit
vegetables
crop
group.

At
each
test
location,
a
total
of
six
broadcast
foliar
spray
applications
of
the
50%
DF
formulation
were
made
at
0.15­
0.23
lb
ai/
A/
application
with
a
5­
to
10­
day
retreatment
interval,
for
total
seasonal
rates
of
~
1.0
lb
ai/
A
(~
1.1x).
Applications
were
made
in
~
10­
51
gal/
A
of
water
using
ground
equipment.
An
adjuvant
was
added
to
the
spray
mixture
for
all
trials,
except
the
first
two
applications
at
the
two
WI
trials
(
RCNs
97029
and
97031).
Samples
of
mature
cantaloupe,
cucumber,
and
summer
squash
fruits
were
harvested
from
all
test
sites
0,
3,
and
7
days
after
the
last
application
(
DALA).
In
addition,
samples
were
collected
from
two
cucumber
trials
(
RCNs
97023
and
97395)
10
and
15
days
following
the
last
application
of
the
test
formulation
to
evaluate
residue
decline.

Adequate
storage
stability
data
for
kresoxim­
methyl
and
its
metabolites
are
available
to
support
the
storage
conditions
and
intervals
of
field
trial
samples.
The
maximum
storage
intervals
of
samples,
from
harvest
to
analysis,
were
278
days
(
9.1
months)
for
cantaloupes,
295
days
(
9.7
months)
for
cucumbers,
and
314
days
(
10.3
months)
for
squash.

BASF
Method
350/
3­
US
(
or
a
slightly
modified
version
of
the
method),
an
HPLC
method
with
UV
detection
(
270
nm),
was
used
to
determine
residues
of
kresoxim­
methyl
and
its
predominant
metabolites
(
BF
490­
1,
BF
490­
2,
and
BF
490­
9)
in/
on
harvested
samples.
BASF
Method
350/
3­
US
converts
glucose
conjugates
of
BF
490­
B
and
BF
490­
C
to
their
unconjugated
forms
BF
490­
2
and
BF
490­
9,
respectively,
following
enzyme
hydrolysis.
The
parent,
kresoxim­
methyl,
is
converted
to
the
acid
metabolite
BF
490­
1
following
enzymatic
cleavage
and
base
hydrolysis.
The
metabolite
BF
490­
1
is
measured
as
kresoxim­
methyl
equivalents.
The
validated
LOQ
for
each
analyte
was
established
at
0.05
ppm
in
cantaloupes,
cucumbers,
and
summer
squash.
The
method
was
found
to
give
acceptable
recoveries,
and
the
standard
deviations
measured
with
respect
to
recoveries
following
spiking
at
0.05
and
1.0
ppm
were
indicative
of
the
method
having
satisfactory
repeatability.

The
maximum
combined
residues
of
kresoxim­
methyl
and
its
metabolites
BF
490­
2
and
BF
490­
9
in/
on
cucurbit
vegetables
harvested
0
days
following
the
last
of
six
broadcast
foliar
applications
of
the
50%
DF
formulation
for
a
total
seasonal
rate
of
~
1.0
lb
ai/
A
were
<
0.320
ppm
in/
on
cantaloupes,
<
0.220
ppm
in/
on
cucumber,
and
<
0.340
ppm
in/
on
summer
squash.
The
parent
accounted
for
the
majority
of
the
combined
residues;
maximum
individual
residues
of
kresoximmethyl
in/
on
treated
samples
were
0.220
ppm
for
cantaloupes,
0.120
ppm
for
cucumbers,
and
0.240
ppm
for
squash.
Individual
residues
of
metabolites
BF
490­
2
and
BF
490­
9
were
each
below
the
method
LOQ
(<
0.05
ppm)
in/
on
all
treated
samples
collected
at
0­
day
PHI.

In
the
residue
decline
study
conducted
in
CA
(
RCN
97395),
kresoxim­
methyl
residues
generally
declined
in/
on
cucumber
samples
with
increasing
sampling
intervals
following
treatment
with
test
formulation.
Higher
residues
of
kresoxim­
methyl
(
0.092­
0.120
ppm)
were
detected
at
the
0­
and
Kresoxim­
Methyl
Summary
of
Analytical
Chemistry
and
Residue
Data
DP#:
328725
Page
11
of
23
3­
day
PHIs
and
decreased
to
below
the
LOQ
(<
0.05
ppm)
at
the
10­
and
15­
day
PHIs.
Residues
of
BF
490­
2
were
below
the
LOQ
(<
0.05
ppm)
at
all
sampling
intervals.
Residues
of
BF
490­
9
were
variable
but
below
or
close
to
the
LOQ
(<
0.05­
0.082
ppm)
at
all
sampling
intervals.
Residue
decline
data
from
the
decline
study
conducted
in
GA
(
RCN
97023)
were
inconclusive
because
residues
of
kresoxim­
methyl
and
its
metabolites
were
each
below
the
LOQ
(<
0.05
ppm)
at
all
sampling
intervals.

Conclusions.
The
residue
data
for
cantaloupes,
cucumbers,
and
summer
squash,
which
are
the
representative
crops
of
the
cucurbit
vegetable
crop
group,
are
adequate
and
are
supported
by
adequate
storage
stability
data.
The
data­
collection
method
used
for
the
analysis
of
the
residues
of
concern
in/
on
treated
samples
is
also
adequate.
The
results
indicate
that
when
the
50%
DF
formulation
of
kresoxim­
methyl
is
applied
according
to
the
maximum
proposed
label
use
pattern
on
cantaloupes,
cucumbers,
and
summer
squash,
the
proposed
tolerance
of
0.5
ppm
will
not
be
exceeded.
However,
the
petitioner
should
submit
a
revised
Section
F
to
specify
the
HEDassessed
tolerance
of
0.40
ppm
for
the
combined
residues
of
kresoxim­
methyl,
BF
490­
1,
BF
490­
2
(
free
and
glucose
conjugated)
and
BF
490­
9
(
free
and
glucose
conjugated)
on
"
Vegetable,
cucurbit,
group
9"
(
see
section
860.1550
Proposed
Tolerances,
below).

860.1520
Processed
Food
and
Feed
Data
requirements
pertaining
to
this
guideline
topic
are
not
relevant
to
this
petition
because
there
is
no
processed
food/
feed
item
associated
with
the
proposed
use
on
cucurbit
vegetables.

860.1650
Submittal
of
Analytical
Reference
Standards
Analytical
standards
for
kresoxim­
methyl
are
currently
available
in
the
National
Pesticide
Standards
Repository.
However,
standards
for
the
regulated
metabolites
(
BF
490­
1,
BF
490­
2,
and
BF
490­
9)
are
not
available
and
are
required.
Analytical
reference
standards
of
kresoximmethyl
and
its
metabolites
should
be
supplied
and
supplies
replenished
as
requested
by
the
Repository.
The
reference
standards
should
be
sent
to
the
Analytical
Chemistry
Lab,
which
is
located
at
Fort
Meade,
to
the
attention
of
either
Theresa
Cole
or
Frederic
Siegelman
at
the
following
address:

USEPA
National
Pesticide
Standards
Repository/
Analytical
Chemistry
Branch/
OPP
701
Mapes
Road
Fort
George
G.
Meade,
MD
20755­
5350
(
Note
that
the
mail
will
be
returned
if
the
extended
zip
code
is
not
used.)
Kresoxim­
Methyl
Summary
of
Analytical
Chemistry
and
Residue
Data
DP#:
328725
Page
12
of
23
860.1850
Confined
Accumulation
in
Rotational
Crops
45101404.
der.
doc
BASF
Corporation
has
submitted
a
confined
rotational
crop
study
with
kresoxim­
methyl.
The
radiolabeled
test
substance,
[
14C]
kresoxim­
methyl
[
labeled
uniformly
in
the
benzyl
(
B)
ring,
specific
activity
of
6.28
MBq/
mg],
was
mixed
with
methanol/
water
and
applied
to
bare
sandy
loam
soil
in
eight
planting
containers
at
0.3
lb
ai/
A/
application.
Four
applications
were
made
at
7­
day
intervals
for
a
total
rate
of
1.2
lb
ai/
A.
Radish,
Swiss
chard,
and
sorghum
were
planted
in
the
treated
soil
as
rotational
crops
at
PBIs
of
14/
28,
91,
210/
245,
and
394/
423/
434
days.

TRR,
expressed
as
kresoxim­
methyl
equivalents,
accumulated
at
 
0.01
ppm
in
all
rotated
crops
planted
14/
28,
91,
or
210/
245
days
following
applications
of
[
benzyl­
UL­
14C]
kresoxim­
methyl
to
bare
soil
for
a
total
application
rate
of
1.2
lb
ai/
A.
Overall,
TRR
were
highest
from
the
14/
28­
day
PBI
and
subsequently
decreased
at
later
PBIs.
At
the
14­
day
PBI,
residues
were
0.858
and
0.612
ppm
in
radish
tops
and
roots,
respectively,
0.496
ppm
in
sorghum
forage,
0.597
ppm
in
sorghum
fodder,
and
0.156
ppm
in
sorghum
seed.
At
the
28­
day
PBI,
residues
were
0.384
ppm
for
Swiss
chard.
At
the
91­
day
PBI,
residues
were
0.197
and
0.182
ppm
in
radish
tops
and
roots,
respectively,
0.339
ppm
in
Swiss
chard,
and
0.054­
0.096
ppm
in
sorghum
forage,
fodder,
and
seed.
At
the
210­
day
PBI,
residues
were
0.013­
0.033
ppm
in
radish
tops
and
roots,
and
Swiss
chard.
At
the
245­
day
PBI,
residues
were
0.010­
0.014
ppm
in
sorghum
forage,
fodder,
and
seed.
At
the
394/
423/
434­
day
PBI,
TRR
were
<
0.01
ppm
in
all
rotated
crops.

In
general,
the
fractionation
procedures
used
to
characterize/
identify
residues
resulted
in
three
fractions:
organic
extract
(
dichloromethane
(
DCM)/
ethyl
acetate
(
EtOAc)),
methanol/
water
extract,
and
0.1
N
HCl
hydrolysate.
Residue
characterization
of
rotational
crops
focused
on
the
earliest
PBIs
(
14/
28
and
91
day)
since
they
bore
the
greatest
amount
of
residues.
Samples
from
the
210/
245­
day
PBI
were
extracted
but
not
analyzed
because
of
low
residues
( 
0.01
ppm)
in
the
extracts.

At
the
14/
28­
day
PBI,
the
majority
of
the
radioactivity
(
58­
78%
TRR)
was
extracted
into
methanol/
water,
except
for
sorghum
seed
(
11%
TRR
in
the
methanol/
water
extract).
The
majority
of
the
radioactivity
(
57%
TRR)
in
sorghum
seed
was
released
with
subsequent
acid
hydrolysis;
5­
26%
TRR
was
released
with
acid
hydrolysis
of
the
other
rotated
matrices.
In
the
91­
day
PBI
samples,
solvent­
extractable
residues
were
reduced,
while
a
larger
amount
of
radioactivity
was
released
with
acid
hydrolysis.
Base
digestion
of
nonextractable
residues
released
an
additional
5­
9%
TRR
from
most
matrices,
and
24­
28%
TRR
from
radish
roots
and
sorghum
seed.
Nonextractable
residues
remaining
following
extraction/
hydrolysis
accounted
for
<
0.03
ppm
in
all
rotational
crop
matrices;
accountabilities
ranged
~
90­
114%.
Residues
were
identified
and
quantitated
primarily
by
HPLC
and
liquid
chromatography/
mass
spectroscopy
(
LC/
MS)
cochromatography.
These
methods
successfully
identified
the
predominant
residues
in
rotated
crops.

At
the
14/
28­
and
91­
day
PBI,
total
identified
residues
ranged
5­
45%
in
rotated
crop
commodities
other
than
sorghum
seed;
no
residues
were
identified
in
rotated
sorghum
seed.
The
parent,
kresoxim­
methyl,
was
not
identified
in
any
rotational
crop
commodity
at
any
PBI.
Two
metabolites,
the
glucose
conjugates
of
490
M2
and
490
M9,
were
identified
in
the
rotated
crop
matrices
(
except
sorghum
seed).
The
490
M2
glucoside
was
found
to
be
the
major
metabolite
Kresoxim­
Methyl
Summary
of
Analytical
Chemistry
and
Residue
Data
DP#:
328725
Page
13
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23
identified
in
14­
and
91­
day
PBI
sorghum
forage
(
12.3­
13.5%
TRR,
0.013­
0.061
ppm)
and
14­
day
PBI
sorghum
fodder
(
16.8%
TRR,
0.100
ppm);
the
490
M2
glucoside
represented
4­
8%
TRR
in
radish
tops
and
roots
(
both
PBIs).
The
490
M9
glucoside
was
found
to
be
the
major
metabolite
identified
in
14­
and
91­
day
PBI
radish
top
(
13.5­
37.0%
TRR,
0.027­
0.318
ppm),
and
14­
and
91­
day
PBI
radish
root
(
17.5­
24.6%
TRR,
0.044­
0.107
ppm);
the
490
M9
glucoside
represented
7­
9%
in
14­
day
PBI
sorghum
forage
and
fodder.
Both
490
M2
and
490
M9
glucosides
were
detected
at
approximately
equal
amounts
in
28­
day
PBI
Swiss
chard
(
15.5­
16.2%
TRR,
0.060­
0.062
ppm);
however,
in
91­
day
PBI
Swiss
chard,
the
490
M2
glucoside
was
found
at
higher
levels
(
12.0%
TRR,
0.039
ppm)
than
the
490
M9
glucoside
(
5.2%
TRR,
0.017
ppm).
The
490
M2
and
M9
glucosides
co­
eluted
in
91­
day
PBI
sorghum
fodder
as
a
minor
residue
(<
5%
TRR).
A
second
major
peak
in
91­
day
PBI
Swiss
chard,
accounting
for
13.9%
TRR
(
0.047
ppm),
was
tentatively
identified
by
LC/
MS
as
a
glycine
conjugate
of
a
dihydroxylated
metabolite
of
kresoxim­
methyl
(
no
structure
was
proposed).

A
polar
peak
area,
observed
in
the
methanol/
water
extracts
of
all
rotational
crop
commodities,
accounted
for
2.0­
6.0%
TRR
(
0.009­
0.036
ppm)
in
all
matrices,
except
for
sorghum
seed
(
34.8%
TRR,
0.053
ppm)
at
the
14/
28­
day
PBI,
and
7.7­
18.5%
TRR
(
0.009­
0.034
ppm)
in
all
matrices,
except
for
sorghum
seed
(
53.8%
TRR,
0.029
ppm)
at
the
91­
day
PBI.
Further
characterization
of
this
polar
peak,
using
fractions
isolated
from
radish
tops
and
Swiss
chard
(
91­
day
PBI),
indicated
that
the
polar
residue
is
a
cluster
consisting
of
more
than
20
peaks.
Unknown
residues
accounted
for
the
remaining
residues
in
the
rotated
crop
matrices
at
8­
28.5%
TRR;
each
peak
represented
<
7%
TRR
(<
0.05
ppm).
The
petitioner
stated
that
the
radioactivity
released
with
base
digestion
represents
solubilized
lignin,
indicating
that
the
metabolites
of
kresoxim­
methyl
were
incorporated
into
natural
products
in
the
rotated
crops;
5­
9%
TRR
from
most
matrices,
and
24­
28%
TRR
from
radish
roots
and
sorghum
seed.

The
sample
extraction
and
analysis
dates
were
not
provided.
Based
on
the
study
completion
dates,
samples
may
have
been
stored
for
up
to
~
28
months
prior
to
analysis.
The
petitioner
provided
data
demonstrating
that
the
metabolic
profile
is
relatively
stable
in
radish
tops,
Swiss
chard,
and
sorghum
forage
stored
frozen
for
~
18
months.

Based
on
the
results
of
the
study,
the
metabolic
pathway
of
kresoxim­
methyl
in
rotational
crops
involves
the
initial
cleavage
of
the
acid
ester
to
the
free
acid
(
490
M1),
oxidation
of
the
A
ring
to
form
hydroxylated
products
(
490
M2
and
490
M9),
conjugation
of
these
hydroxylated
products
to
glucose
(
490­
B
and
490­
C)
and
final
incorporation
of
these
metabolites
into
natural
products.

Conclusions.
The
nature
of
the
residues
in
rotational
crops
is
adequate
pending
submission
of
supporting
sample
storage
stability
information/
data.
In
the
submitted
confined
rotational
crop
study,
total
radioactive
residues
accumulated
at
 
0.01
ppm
in
all
rotated
crops
(
radish,
Swiss
chard,
and
sorghum)
planted
14/
28,
91,
or
210/
245
days
following
four
applications
of
[
14C]
kresoxim­
methyl
for
a
total
rate
of
1.2
lb
ai/
A
(
1.3x).
The
parent,
kresoxim­
methyl,
was
not
detected
in/
on
any
rotational
crop
commodity
at
any
PBI.
The
major
residue
components
identified
in
rotational
crop
commodities
were
the
glucosides
of
490
M2
and
490
M9.
These
conjugated
metabolites,
490
M2
and
490
M9,
are
converted
to
their
unconjugated
metabolites
BF
490­
2
and
BF
490­
9
following
enzyme
hydrolysis.
Kresoxim­
Methyl
Summary
of
Analytical
Chemistry
and
Residue
Data
DP#:
328725
Page
14
of
23
860.1900
Field
Accumulation
in
Rotational
Crops
45939305.
der.
doc
(
Cabbage,
Radish,
and
Wheat)

Table
6.
Summary
of
Residue
Data
with
Kresoxim­
Methyl
on
Rotational
Crops.

Residue
Levels
(
ppm)
Commodity
Applic.
Rate
(
lb
ai/
A)
PBI
(
days)
Analyte
n
Min.
Max.
HAFT1
Median
Mean
Std.
Dev.

BF
490­
2
4
<
0.05
<
0.05
<
0.05
0.025
0.025
0.0
BF
490­
9
4
<
0.05
<
0.05
<
0.05
0.025
0.025
0.0
Cabbage
1.054­
1.057
14
Combined
4
<
0.10
<
0.10
<
0.10
0.05
0.05
0.0
BF
490­
2
4
<
0.05
<
0.05
<
0.05
0.025
0.025
0.0
BF
490­
9
4
<
0.05
<
0.05
<
0.05
0.025
0.025
0.0
Radish,
root
1.054­
1.057
14
Combined
4
<
0.10
<
0.10
<
0.10
0.05
0.05
0.0
BF
490­
2
4
<
0.05
<
0.05
<
0.05
0.025
0.025
0.0
BF
490­
9
4
<
0.05
<
0.05
<
0.05
0.025
0.025
0.0
Radish,
tops
1.054­
1.057
14
Combined
4
<
0.10
<
0.10
<
0.10
0.05
0.05
0.0
BF
490­
2
10
<
0.05
<
0.05
<
0.05
0.025
0.025
0.0
BF
490­
9
10
<
0.05
<
0.05
<
0.05
0.025
0.025
0.0
Wheat,
forage
1.048­
1.054
14
Combined
10
<
0.10
<
0.10
<
0.10
0.05
0.05
0.0
BF
490­
2
8
<
0.05
<
0.05
<
0.05
0.025
0.025
0.0
BF
490­
9
8
<
0.05
<
0.05
<
0.05
0.025
0.025
0.0
Wheat,
hay
1.048­
1.054
14
Combined
8
<
0.10
<
0.10
<
0.10
0.05
0.05
0.0
BF
490­
2
6
<
0.05
<
0.05
<
0.05
0.025
0.025
0.0
BF
490­
9
6
<
0.05
<
0.05
<
0.05
0.025
0.025
0.0
Wheat,
straw
1.048­
1.054
14
Combined
6
<
0.10
<
0.10
<
0.10
0.05
0.05
0.0
BF
490­
2
8
<
0.05
<
0.05
<
0.05
0.025
0.025
0.0
BF
490­
9
8
<
0.05
<
0.05
<
0.05
0.025
0.025
0.0
Wheat,
grain
1.048­
1.054
14
Combined
8
<
0.10
<
0.10
<
0.10
0.05
0.05
0.0
1HAFT
=
Highest
Average
Field
Trial.

BASF
Corporation
has
submitted
a
limited
field
rotational
crop
study
with
kresoxim­
methyl
on
the
representative
crops
cabbage
(
leafy
vegetable),
radish
(
root
vegetable),
and
wheat
(
cereal
grain).
Six
field
trials
were
conducted
at
two
test
sites,
in
Regions
2
(
GA)
and
10
(
CA)
for
each
crop.
At
each
site,
six
broadcast
foliar
spray
applications
of
a
50%
DF
formulation
of
kresoximmethyl
were
made
with
an
adjuvant
to
the
primary
crop,
cucumbers,
at
0.17­
0.18
lb
ai/
A/
application,
for
total
application
rates
of
1.05­
1.06
lb
ai/
A
(~
1.2x).
Applications
of
the
test
formulation
began
35
days
prior
to
harvest
of
cucumbers.
When
the
primary
crop
(
cucumbers)
reached
maturity,
they
were
harvested
and
the
treatment
plots
were
planted
with
rotational
crops
of
cabbage,
radish,
and
wheat
at
PBIs
of
~
14,
30,
and
45
days.
The
rotational
crops
were
allowed
to
grow
and
mature
according
to
good
agricultural
practices.
Samples
of
cabbage
(
with
and
without
wrapper
leaves),
radish
roots
and
tops,
and
wheat
forage,
hay,
straw,
and
grain
were
collected
at
crop
maturity.

Samples
of
rotational
crop
commodities
from
the
14­
day
PBI
were
analyzed
for
residues
of
the
glycoside
metabolites,
BF
490­
B
and
BF
490­
C,
as
BF
490­
2
and
BF
490­
9,
respectively,
using
a
modified
version
of
BASF
Method
350/
3­
US.
BASF
Method
350/
3­
US,
an
HPLC
method
with
UV
detection
(
270
nm),
is
the
current
plant
enforcement
method
for
the
determination
of
residues
of
kresoxim­
methyl
and
its
predominant
metabolites
(
BF
490­
1,
BF
490­
2,
and
BF
490­
9).
This
method
was
revised
in
the
current
study
to
measure
only
residues
of
the
glycoside
metabolites
(
BF
Kresoxim­
Methyl
Summary
of
Analytical
Chemistry
and
Residue
Data
DP#:
328725
Page
15
of
23
490­
2
and
BF
490­
9)
since
these
glycoside
metabolites
were
the
predominant
residues
identified
in
a
confined
rotational
crop
study
(
see
the
860.1850
DER
for
MRID
45101404).
A
modification
of
the
method
for
rotational
crop
commodities
included
final
determination
by
LC/
MS/
MS
in
lieu
of
HPLC.
The
validated
LOQs
for
metabolites
BF
490­
2
and
BF
490­
9,
when
using
the
LC/
MS/
MS
method,
were
each
0.05
ppm,
with
a
total
of
0.10
ppm.
The
LOD,
defined
as
the
lowest
standard
level
injected
with
the
analysis
sets
was
equivalent
to
0.02
ppm
for
each
analyte.
The
method
is
adequate
for
data
collection
based
on
acceptable
concurrent
method
recovery
data.

Adequate
storage
stability
data
are
available
to
support
the
storage
conditions
and
intervals
of
samples
collected
from
the
current
study.
The
maximum
storage
intervals,
from
harvest
to
analysis,
were
295
days
(
9.7
months)
for
cabbage
(
with
and
without
wrapper
leaves),
344
days
(
11.3
months)
for
radish
(
roots
and
tops),
292
months
(
9.6
months)
for
wheat
forage,
194
days
(
6.4
months)
for
wheat
hay,
161
days
(
5.3
months)
for
wheat
straw
and
grain.
To
support
sample
storage
conditions
and
intervals,
the
petitioner
cited
storage
stability
data
submitted
in
conjunction
with
the
confined
rotational
crop
study
(
refer
to
860.1850
DER
for
MRID
45101404);
these
data
demonstrate
that
the
percentages
of
total
radioactive
residues
of
BF
490­
2
and
BF
490­
9
remained
constant
under
frozen
conditions
in
Swiss
chard
and
sorghum
for
up
to
18
months.
The
petitioner
also
included
a
storage
stability
study
investigating
the
recovery
of
fortified
residues
of
kresoxim­
methyl
and
its
glucose
conjugate
metabolites
BF
490­
B
and
BF
490­
C
in/
on
apples
(
refer
to
the
860.1380
DER
for
MRID
45101403).
These
data
indicate
that
kresoxim­
methyl,
BF
490­
B,
and
BF
490­
C
are
reasonably
stable
under
frozen
conditions
in/
on
apples
for
up
to
12
months.
The
petitioner
stated
that
a
storage
stability
study
has
been
initiated
for
the
glycoside
metabolites
in
cabbage,
radish
root,
wheat
grain,
and
wheat
straw;
these
supplemental
data
will
be
submitted
to
the
Agency
upon
study
completion.

The
study
results
indicate
that
at
the
14­
day
PBI,
residues
of
BF
490­
2
and
BF
490­
9
were
each
below
the
LOQ
(<
0.05
ppm)
in/
on
cabbage
(
with
and
without
wrapper
leaves),
radish
roots
and
tops,
and
wheat
forage,
hay,
straw,
and
grain.
Because
residues
were
below
the
LOQ
in
all
samples
of
rotated
crop
commodities
from
the
14­
day
PBI,
samples
from
the
30­
and
45­
day
PBIs
were
not
analyzed.

Conclusions.
The
submitted
limited
field
rotational
crop
study
with
kresoxim­
methyl
is
adequate.
Representative
rotational
crops
of
cabbage
(
leafy
vegetable),
radish
(
root
vegetable),
and
wheat
(
cereal
grain)
were
planted
at
intervals
of
~
14,
30,
and
45
days
after
the
primary
crop
(
cucumbers)
was
treated
at
~
1.2x
and
harvested
at
maturity.
Only
residues
of
the
glycoside
metabolites
(
BF
490­
2
and
BF
490­
9)
were
measured
in
this
study
since
these
glycoside
metabolites
were
the
predominant
residues
identified
in
the
confined
rotational
crop
study.
The
results
indicate
that
at
a
PBI
of
14
days,
residues
of
BF
490­
2
and
BF
490­
9
were
each
below
the
LOQ
(<
0.05
ppm)
in/
on
cabbage
(
with
and
without
wrapper
leaves),
radish
roots
and
tops,
and
wheat
forage,
hay,
straw,
and
grain.
Because
residues
were
below
the
LOQ
in
all
samples
of
rotated
crop
commodities
from
the
14­
day
PBI,
samples
from
the
30­
and
45­
day
PBIs
were
not
analyzed.
Based
on
these
data,
HED
concludes
that
tolerances
for
rotational
crop
commodities
are
not
required
for
the
purpose
of
this
petition
provided
the
label
for
Sovran
®
Fungicide
(
EPA
Reg.
No.
7969­
154)
is
amended
to
specify
a
PBI
interval
of
14
days.
Kresoxim­
Methyl
Summary
of
Analytical
Chemistry
and
Residue
Data
DP#:
328725
Page
16
of
23
860.1550
Proposed
Tolerances
The
proposed
tolerance
expression,
listed
in
the
petition's
Section
F,
is
expressed
in
terms
of
the
combined
residues
of
the
fungicide
kresoxim­
methyl;
i.
e.,
methyl
(
E)­
2­
methoxyimino­
2­[
2­(
otolyloxmethyl
phenyl]
acetate
and
its
metabolites
2­[
o­(
o­
hydroxymethylphenoxymethyl)
phenyl]­
2­(
methoxyimino)
acetic
acid
and
2­[
o­(
p­
hydroxymethylphenoxymethyl)
phenyl]­
2­
(
methoxyimino)
acetic
acid.

The
HED
MARC
has
determined
that
the
tolerance
expression
for
kresoxim­
methyl
on
pome
fruits,
grapes,
pecans,
and
related
crops
(
fruit
or
fruiting
vegetables)
will
include
kresoxim­
methyl,
BF
490­
1,
BF
490­
2
(
free
and
glucose
conjugated)
and
BF
490­
9
(
free
and
glucose
conjugated).
The
petitioner
should
thus
submit
a
revised
Section
F
to
reflect
all
the
residues
of
concern
[
kresoxim­
methyl,
BF
490­
1,
BF
490­
2
(
free
and
glucose
conjugated)
and
BF
490­
9
(
free
and
glucose
conjugated)]
in
the
tolerance
expression
as
specified
in
40
CFR
§
180.554(
a)(
1):
"
combined
residues
of
the
fungicide
kresoxim­
methyl
(
methyl
(
E)­
2­[
2­(
2­
methylphenoxy)­
methyl]
phenyl­
2­(
methoxyimido)
acetate)
and
its
metabolites
as
follows:
(
E)­
2­[
2­(
2­
methylphenoxy)
methyl]­
phenyl­
2­(
methoxyimido)
acetic
acid;
(
E)­
2­[
2­(
2­
hydroxymethylphenoxy)
methyl]­
phenyl­
2­(
methoxyimido)
acetic
acid
(
free
and
glucose
conjugated);
and
(
E)­
2­[
2­(
4­
hydroxy­
2­
methylphenoxy)­
methyl]
phenyl­
2­(
methoxyimido)
acetic
acid
(
free
and
glucose
conjugated)."

Codex,
Canada,
and
Mexico
have
established
maximum
residue
limits
(
MRLs)
for
kresoximmethyl
on
various
crop
commodities;
see
International
Residue
Limit
Status
(
IRLS)
sheet
in
Appendix
III.
The
Codex
and
Mexico
residue
definitions
for
kresoxim­
methyl
in
plant
commodities
are
in
terms
of
the
parent,
and
a
Codex
MRL
is
established
for
cucumber
at
0.05
ppm.
The
U.
S.
and
Codex
tolerances/
MRLs
are
compatible
not
with
regard
to
tolerance
expression
and
the
levels
can
not
be
harmonized
as
the
recommended
tolerance
(
0.40
ppm)
is
significantly
higher
than
the
Codex
MRL
(
0.05
ppm).

The
residue
field
trial
data
for
cantaloupes,
cucumbers,
and
summer
squash,
which
reflect
the
proposed
use
pattern
on
cucurbit
vegetables,
were
entered
into
a
tolerance
spreadsheet
as
specified
by
the
Guidance
for
Setting
Pesticide
Tolerances
Based
on
Field
Trial
Data
SOP;
see
Appendix
II.
The
recommended
tolerance
level
for
kresoxim­
methyl
on
"
Vegetable,
cucurbit,
group
9"
is
0.40
ppm.
The
petitioner
should
submit
a
revised
Section
F
to
specify
the
HEDassessed
tolerance
of
0.40
ppm
and
to
revise
commodity
definition
from
"
Crop
Group
9,
Cucurbit
Vegetables
Group"
to
"
Vegetable,
cucurbit,
group
9."
A
tolerance
summary
assessment
for
this
petition
is
listed
in
Table
7.

Table
7.
Tolerance
Summary
for
Kresoxim­
Methyl
Commodity
Established/
Proposed
Tolerance
(
ppm)
Recommended
Tolerance
(
ppm)
Comments;
Correct
Commodity
Definition
Crop
Group
9,
Cucurbit
Vegetables
Group
0.5
0.40
Vegetable,
cucurbit,
group
9
Kresoxim­
Methyl
Summary
of
Analytical
Chemistry
and
Residue
Data
DP#:
328725
Page
17
of
23
Attachments:
Appendix
I
­
Chemical
Name
and
Structure
Tables
Appendix
II
­
Tolerance
Assessment
Calculations
Appendix
III
­
International
Residue
Limit
Status
Sheet
References
DP
Barcode:
D255097
Subject:
PP#
7F04880.
Kresoxim­
Methyl
in/
on
Pome
Fruits,
Grapes
and
Pecans.
Evaluation
of
Residue
Data
and
Analytical
Methods.
Chemical
129111.
Case
289033.
Submission
S537007.
From:
T.
Bloem
To:
M.
Waller/
L.
Kutney
Dated:
4/
12/
99
MRIDs:
44341026,
4434140­
44341077,
44421006­
44421008,
44539708­
44539713
DOCUMENT
TRACKING
RDI:
RAB1
Chemists
(
5/
24/
06)
Petition
Number:
3E6594
DP#:
328725
PC
Code:
129111
Template
Version
September
2005
Kresoxim­
Methyl
Summary
of
Analytical
Chemistry
and
Residue
Data
DP#:
328725
Page
18
of
23
Appendix
I
Chemical
Name
and
Structures
of
Metabolites
Identified
in
a
Confined
Accumulation
Study
Identification
of
Compounds
from
the
Confined
Rotational
Crop
Study
(
MRID
45101404)

Common
name/
code
Figure
C.
3.1
ID
No.
Chemical
name
Chemical
structure
490
M2
Glucoside
(
490­
B)

O
N
O
CH
3
O
O
H
Glu­
O
490
M9
Glucoside
(
490­
C)

O
N
O
CH
3
O
O
H
Glu­
O
CH
3
Glycine
conjugate
of
a
dihydroxylated
metabolite
of
kresoxim­
methyl
1
No
structure
provided
1
Proposed
identification
based
on
LC/
MS/
MS.

Chemical
Name
and
Structures
of
Regulated
Metabolites
Common
Name
and
Company
Code
Structure
BF
490­
1
(
acid)

(
E)­
2­[
2­(
2­
methylphenoxy)
methyl]­
phenyl­
2­(
methoxyimido)
acetic
acid
O
N
O
CH
3
O
O
H
CH
3
BF
490­
2
(
hydroxymethyl
metabolite)

(
E)­
2­[
2­(
2­
hydroxymethylphenoxy)
methyl]­
phenyl­
2­
(
methoxyimido)
acetic
acid
O
N
O
CH
3
O
O
H
OH
BF
490­
9
(
para
hydroxy
metabolite)

(
E)­
2­[
2­(
4­
hydroxy­
2­
methylphenoxy)­
methyl]
phenyl­
2­
(
methoxyimido)
acetic
acid
O
N
O
CH
3
O
O
H
CH
3
O
H
Kresoxim­
Methyl
Summary
of
Analytical
Chemistry
and
Residue
Data
DP#:
328725
Page
19
of
23
Appendix
II
­
Tolerance
Assessment
Calculations
The
datasets
used
to
establish
a
crop
group
tolerance
for
kresoxim­
methyl
on
cucurbit
vegetables
consisted
of
field
trial
data
representing
application
rates
of
1.0­
1.1
lb
ai/
A
(
6
applications
at
0.15­
0.23
lb
ai/
A/
application)
with
a
0­
day
PHI.
As
specified
by
the
Guidance
for
Setting
Pesticide
Tolerances
Based
on
Field
Trial
Data
SOP,
the
field
trial
application
rates
and
PHIs
are
within
25%
of
the
maximum
label
application
rate
and
minimum
label
PHI,
respectively.
The
residues
values
used
to
calculate
the
tolerance
are
provided
in
Table
II­
1.

There
cantaloupe,
cucumber,
and
summer
squash
trials
were
evaluated
individually.
The
highest
residue
levels
were
seen
in
the
summer
squash
trials.
The
result
from
the
approximate
Shapiro­
Francia
test
statistic
(
Figure
II­
2)
indicated
that
the
assumption
of
lognormality
should
be
rejected
for
summer
squash.
Visual
inspection
of
the
lognormal
probability
plot
(
Figure
II­
1)
provided
in
the
spreadsheet
confirmed
that
the
dataset
is
not
lognormal.

Since
the
field
trial
data
for
kresoxim­
methyl
on
cucurbit
vegetables
are
not
lognormal,
the
upper
bound
on
the
89th
percentile
should
be
selected
as
the
tolerance
value
(
distribution­
free
method).
Using
the
rounding
procedure
as
outlined
in
the
Guidance
for
Setting
Pesticide
Tolerances
Based
on
Field
Trial
Data
SOP,
the
CA
Method
rounds
to
the
value
0.40
ppm.
Therefore,
0.40
ppm
is
the
recommended
tolerance
level
for
kresoxim­
methyl
on
"
Vegetable,
cucurbit
(
Group
9)."

Chemical:
Kresoxim­
Methyl
Crop:
Cantaloupe
PHI:
0
days
App.
Rate:
1.044­
1.0552
lb
ai/
A
Submitter:

Residues
LN(
Residues)
Zscores
0.198
­
1.62
0.54
0.235
­
1.45
0.79
0.169
­
1.78
­
0.79
0.185
­
1.69
­
0.10
0.190
­
1.66
0.10
0.192
­
1.65
0.31
0.299
­
1.21
1.11
0.320
­
1.14
1.64
0.154
­
1.87
­
1.11
0.150
­
1.90
­
1.64
0.169
­
1.78
­
0.54
0.173
­
1.75
­
0.31
Kresoxim­
Methyl
Summary
of
Analytical
Chemistry
and
Residue
Data
DP#:
328725
Page
20
of
23
Chemical:
Kresoxim­
Methyl
Crop:
Cucumber
PHI:
0
days
App.
Rate:
1.0462­
1.0695
lb
ai/
A
Submitter:

Residues
LN(
Residues)
Zscores
0.150
­
1.90
­
1.77
0.150
­
1.90
­
1.28
0.172
­
1.76
0.76
0.173
­
1.75
0.99
0.150
­
1.90
­
0.99
0.150
­
1.90
­
0.76
0.150
­
1.90
­
0.57
0.150
­
1.90
­
0.40
0.150
­
1.90
­
0.23
0.150
­
1.90
­
0.08
0.150
­
1.90
0.08
0.150
­
1.90
0.23
0.150
­
1.90
0.40
0.150
­
1.90
0.57
0.192
­
1.65
1.28
0.220
­
1.51
1.77
Chemical:
Kresoxim­
Methyl
Crop:
Squash,
summer
PHI:
0
days
App.
Rate:
1.049­
1.0742
lb
ai/
A
Submitter:

Residues
LN(
Residues)
Zscores
0.150
­
1.90
­
1.55
0.150
­
1.90
­
1.00
0.150
­
1.90
­
0.66
0.150
­
1.90
­
0.38
0.150
­
1.90
­
0.12
0.150
­
1.90
0.12
0.150
­
1.90
0.38
0.152
­
1.88
0.66
0.297
­
1.21
1.00
0.340
­
1.08
1.55
Kresoxim­
Methyl
Summary
of
Analytical
Chemistry
and
Residue
Data
DP#:
328725
Page
21
of
23
Figure
II­
1.
Lognormal
Probability
Plot
of
Kresoxim­
Methyl
Field
Trial
Data
for
Cucurbits.

Lognormal
Probability
Plot
99.9
99
98
95
90
80
70
50
30
20
10
5
2
1
0.1
1.0000
0.5000
0.2500
0.1250
y
=
0.239x
­
1.6242
R2
=
0.8736
Percentiles
Concentrations
EPA
Kresoxim­
Methyl
Cantaloupe
0
days
1.044­
1.0552
lb
ai/
A
Lognormal
Probability
Plot
99.9
99
98
95
90
80
70
50
30
20
10
5
2
1
0.1
1.0000
0.5000
0.2500
0.1250
y
=
0.0902x
­
1.8403
R2
=
0.573
Percentiles
Concentrations
EPA
Kresoxim­
Methyl
Cucumber
0
days
1.0462­
1.0695
lb
ai/
A
Lognormal
Probability
Plot
99.9
99
98
95
90
80
70
50
30
20
10
5
2
1
0.1
1.0000
0.5000
0.2500
0.1250
y
=
0.246x
­
1.7457
R
2
=
0.531
Percentiles
Concentrations
EPA
Kresoxim­
Methyl
Squash,
summer
0
days
1.049­
1.0742
lb
ai/
A
Kresoxim­
Methyl
Summary
of
Analytical
Chemistry
and
Residue
Data
DP#:
328725
Page
22
of
23
Figure
II­
2.
Tolerance
Spreadsheet
Summary
of
Kresoxim­
Methyl
Field
Trial
Data
for
Cucurbit
Vegetables.

C
h
e
m
i
c
a
l
:
K
r
e
s
o
x
i
m
­
M
e
t
h
y
l
C
r
o
p
:
C
a
n
t
a
l
o
u
p
e
P
H
I
:
0
d
a
y
s
A
p
p
.
R
a
t
e
:
.
0
4
4
­
1
.
0
5
5
2
l
b
a
i
/
A
S
u
b
m
i
t
t
e
r
:

n
:
1
2
m
i
n
:
0
.
1
5
m
a
x
:
0
.
3
2
m
e
d
i
a
n
;
0
.
1
9
a
v
e
r
a
g
e
:
0
.
2
0
9
5
t
h
P
e
r
c
e
n
t
i
l
e
9
9
t
h
P
e
r
c
e
n
t
i
l
e
9
9
.
9
t
h
P
e
r
c
e
n
t
i
l
e
0
.
3
0
0
.
3
5
0
.
4
0
(
0
.
4
0
)
(
0
.
4
5
)
(
­
­
)
0
.
3
0
0
.
3
5
0
.
4
5
(
0
.
4
0
)
(
0
.
5
0
)
(
­
­
)
0
.
5
0
0
.
4
0
U
P
L
M
e
d
i
a
n
9
5
t
h
1
.
4
0
.
8
7
3
6
p
­
v
a
l
u
e
>
0
.
0
5
:
D
o
n
o
t
r
e
j
e
c
t
l
o
g
n
o
r
m
a
l
i
t
y
a
s
s
u
m
p
t
i
o
n
A
p
p
r
o
x
i
m
a
t
e
S
h
a
p
i
r
o
­
F
r
a
n
c
i
a
N
o
r
m
a
l
i
t
y
T
e
s
t
E
U
M
e
t
h
o
d
I
I
D
i
s
t
r
i
b
u
t
i
o
n
­
F
r
e
e
C
a
l
i
f
o
r
n
i
a
M
e
t
h
o
d
µ
+
3
 
E
U
M
e
t
h
o
d
I
N
o
r
m
a
l
E
U
M
e
t
h
o
d
I
L
o
g
N
o
r
m
a
l
C
h
e
m
i
c
a
l
:
K
r
e
s
o
x
i
m
­
M
e
t
h
y
l
C
r
o
p
:
C
u
c
u
m
b
e
r
P
H
I
:
0
d
a
y
s
A
p
p
.
R
a
t
e
:
.
0
4
6
2
­
1
.
0
6
9
5
l
b
a
i
/
A
S
u
b
m
i
t
t
e
r
:

n
:
1
6
m
i
n
:
0
.
1
5
m
a
x
:
0
.
2
2
m
e
d
i
a
n
;
0
.
1
5
a
v
e
r
a
g
e
:
0
.
1
6
9
5
t
h
P
e
r
c
e
n
t
i
l
e
9
9
t
h
P
e
r
c
e
n
t
i
l
e
9
9
.
9
t
h
P
e
r
c
e
n
t
i
l
e
0
.
2
0
0
.
2
5
0
.
2
5
(
0
.
2
5
)
(
0
.
2
5
)
(
­
­
)
0
.
2
0
0
.
2
5
0
.
2
5
(
0
.
2
5
)
(
0
.
2
5
)
(
­
­
)
0
.
3
5
0
.
2
5
U
P
L
M
e
d
i
a
n
9
5
t
h
1
.
0
0
.
5
7
3
0
p
­
v
a
l
u
e
<
=
0
.
0
1
:
R
e
j
e
c
t
l
o
g
n
o
r
m
a
l
i
t
y
a
s
s
u
m
p
t
i
o
n
A
p
p
r
o
x
i
m
a
t
e
S
h
a
p
i
r
o
­
F
r
a
n
c
i
a
N
o
r
m
a
l
i
t
y
T
e
s
t
E
U
M
e
t
h
o
d
I
I
D
i
s
t
r
i
b
u
t
i
o
n
­
F
r
e
e
C
a
l
i
f
o
r
n
i
a
M
e
t
h
o
d
µ
+
3
 
E
U
M
e
t
h
o
d
I
N
o
r
m
a
l
E
U
M
e
t
h
o
d
I
L
o
g
N
o
r
m
a
l
C
h
e
m
i
c
a
l
:
K
r
e
s
o
x
i
m
­
M
e
t
h
y
l
C
r
o
p
:
S
q
u
a
s
h
,
s
u
m
m
e
r
P
H
I
:
0
d
a
y
s
A
p
p
.
R
a
t
e
:
.
0
4
9
­
1
.
0
7
4
2
l
b
a
i
/
A
S
u
b
m
i
t
t
e
r
:

n
:
1
0
m
i
n
:
0
.
1
5
m
a
x
:
0
.
3
4
m
e
d
i
a
n
;
0
.
1
5
a
v
e
r
a
g
e
:
0
.
1
8
9
5
t
h
P
e
r
c
e
n
t
i
l
e
9
9
t
h
P
e
r
c
e
n
t
i
l
e
9
9
.
9
t
h
P
e
r
c
e
n
t
i
l
e
0
.
3
5
0
.
4
0
0
.
4
5
(
0
.
4
0
)
(
0
.
5
0
)
(
­
­
)
0
.
3
0
0
.
4
0
0
.
5
0
(
0
.
4
5
)
(
0
.
7
0
)
(
­
­
)
0
.
4
0
0
.
4
0
U
P
L
M
e
d
i
a
n
9
5
t
h
1
.
2
0
.
5
3
1
0
p
­
v
a
l
u
e
<
=
0
.
0
1
:
R
e
j
e
c
t
l
o
g
n
o
r
m
a
l
i
t
y
a
s
s
u
m
p
t
i
o
n
A
p
p
r
o
x
i
m
a
t
e
S
h
a
p
i
r
o
­
F
r
a
n
c
i
a
N
o
r
m
a
l
i
t
y
T
e
s
t
E
U
M
e
t
h
o
d
I
I
D
i
s
t
r
i
b
u
t
i
o
n
­
F
r
e
e
C
a
l
i
f
o
r
n
i
a
M
e
t
h
o
d
µ
+
3
 
E
U
M
e
t
h
o
d
I
N
o
r
m
a
l
E
U
M
e
t
h
o
d
I
L
o
g
N
o
r
m
a
l
Kresoxim­
Methyl
Summary
of
Analytical
Chemistry
and
Residue
Data
DP#:
328725
Page
23
of
23
Appendix
III
 
IRLS
Sheet
INTERNATIONAL
RESIDUE
LIMIT
STATUS
Chemical
Name:
methyl
(
E)­
2­
methoxyimino­
2­[
2­
(
o­
tolyloxymethyl)
phenyl]
acetate
Common
Name:
Kresoxim­
methyl
X
Proposed
tolerance

Reevaluated
tolerance

Other
Date:
1/
25/
06
Codex
Status
(
Maximum
Residue
Limits)
U.
S.
Tolerances

No
Codex
proposal
step
6
or
above

No
Codex
proposal
step
6
or
above
for
the
crops
requested
Petition
Number:
PP#
3E6594
DP#:
313836
Other
Identifier:

Reviewer/
Branch:
G.
Kramer
Residue
definition
(
step
8/
CXL):
Plant
commodities:
Kresoxim­
methyl
Livestock
commodities:
Alpha­(
p­
hydroxy­
o­
tolyloxy)­
otolyl
methoxyimino)
acetic
acid,
expressed
as
Kresoxim­
Methyl
Residue
definition:
Kresoxim­
methyl
[
methyl
(
E)­
2­
methoxyimino­
2­[
2­(
o­
tolyloxymethyl)
phenyl]
acetate]
and
its
metabolites
2­[
o­(
o­
hydroxymethyl
phenoxymethyl)
phenyl]
2­(
methoxyimino)
acetic
acid
and
2­[
o­(
p­
hydroxymethylphenoxymethyl)
phenyl]­
2­
(
methoxyimino)
acetic
acid
Crop
(
s)
MRL
(
mg/
kg)
Crop(
s)
Tolerance
(
ppm)

Cucumber
0.05*
Crop
Group
9.
Cucurbit
Vegetables
Group:
Citron
melon,
muskmelon;
watermelon;
Chayote;
Chinese
waxgourd;
cucumber;
gherkin;
gourd,
edible;
Momordica
spp.;
pumpkin;
squash,
summer;
squash,
winter
0.5
Limits
for
Canada
Limits
for
Mexico

No
Limits
X
No
Limits
for
the
crops
requested

No
Limits
X
No
Limits
for
the
crops
requested
Residue
definition:
methyl
("
E)­"­(
methoxyimino)­
2­[(
2­
methylphenoxy)
methyl]
benzeneacetate,
including
the
metabolites
(
E)­
2­[
2­(
2­
methylphenoxymethyl)
phenyl]­
2­
methoxyiminoacetic
acid,
2­[
2­(
2­
hydroxymethylphenoxy
methyl)
phenyl]­
2­
methoxyiminoacetic
acid
and
2­[
2­(
4­
hydroxy­
2­
methyl­
phenoxymethyl)
phenyl]­
2­
methoxyiminoacetic
acid
Residue
definition:
Kresoxim­
metil
Crop(
s)
MRL
(
mg/
kg)
Crop(
s)
MRL
(
mg/
kg)

Notes/
Special
Instructions:
S.
Funk,
01/
26/
2006.
