Document ID: EPA-HQ-OPP-2004-0032-0028
Agency: epa
Document Type: Supporting & Related Material
Title: 
Posted Date: 2006-06-28T04:00Z

UNITED
STATES
ENVIRONMENTAL
PROTECTION
AGENCY
WASHINGTON,
D.
C.
20460
OFFICE
OF
PREVENTION,
PESTICIDES
AND
TOXIC
SUBSTANCES
MEMORANDUM
Date:
December
14,
2005
Subject:
Formetanate
Hydrochloride
HED
Revised
Chemistry
Chapter
of
the
RED:
Summary
of
Analytical
Chemistry
and
Residue
Data
(
Phase
4).

DP
Barcode:
D324543
PC
Code:
097301
From:
Danette
Drew,
Chemist
Reregistration
Branch
3
Health
Effects
Division
(
7509C)

Through:
Catherine
Eiden,
Branch
Chief
Reregistration
Branch
3
Health
Effects
Division
(
7509C)

To:
Demson
Fuller
Reregistration
Branch
2
Special
Review
and
Reregistration
Branch
(
7509C)

The
document
"
Formetanate
Hydrochloride
HED
Revised
Chemistry
Chapter
of
the
RED:
Summary
of
Analytical
Chemistry
and
Residue
Data,
3/
27/
03,
D289010"
has
been
revised
herein
to
reflect
current
Special
Local
Need
(
SLN)
registrations.
    
2
  
38
Executive
Summary
Formetanate
hydrochloride
{
m­[[(
dimethylamino)
methylene]
amino]
phenyl
methylcarbamate
hydrochloride}
is
a
miticide/
insecticide
used
on
a
variety
of
fruits
and
alfalfa
grown
for
seed.
The
92%
wettable
powder
formulation
(
Carzol
®
SP)
contains
formetanate
hydrochloride
(
HCl)
as
the
sole
active
ingredient
and
is
registered
for
foliar
or
dormant
applications
using
ground
or
aerial
equipment.
The
registrant
is
Gowan
Company
(
transferred
from
Aventis
CropScience,
formerly
AgrEvo
USA
Company,
on
4/
30/
01).

Formetanate
HCl
was
the
subject
of
a
Reregistration
Standard
Guidance
Document
dated
9/
83;
the
Residue
Chemistry
Chapter
of
the
Guidance
Document
was
completed
on
9/
30/
82.
The
Residue
Chemistry
Chapter
of
the
Formetanate
HCl
Second
Round
Review
(
SRR)
was
issued
on
5/
10/
89.
The
Residue
Chemistry
Chapter
for
the
Reregistration
Eligibility
Decision
(
RED)
was
completed
on
4/
18/
97
and
the
resulting
preliminary
HED
Risk
Assessment
was
issued
4/
6/
99.
Subsequently,
a
Memorandum
of
Agreement
(
MOA)
between
the
registrant
and
the
EPA
was
issued
(
dated
10/
14/
99).
This
MOA
was
drawn
because
the
Agency
is
concerned
that
formetanate
HCl
presents
dietary,
worker,
and
ecological
risks
that
are
not
consistent
with
the
FIFRA
mandate
that
pesticides
must
not
pose
unreasonable
adverse
effects.

The
MOA
stipulated
label
amendments
to
lower
application
rates,
increase
PHIs
(
pre­
harvest
intervals)
and
limit
uses
to
certain
crops
in
an
effort
to
reduce
risks
by
reducing
exposures
associated
with
formetanate
HCl.
The
MOA
requirements,
for
continued
use
of
formetanate
HCl
on
food/
feed
crops,
as
they
pertain
to
residue
chemistry,
include
the
following.

(
A)
Label
instructions
limiting
use
to
one
application
of
one
product
containing
formetanate
hydrochloride
per
growing
season,
for
all
crops.

(
B)
Label
instructions
prohibiting
use
in
Florida.

[(
C)
Label
instructions
prohibiting
use
on
greenhouse
grown
ornamental
plants.]

(
D)
Label
instruction
prohibiting
its
use
on
plums
and
prunes.

(
E)
Label
instructions
restricting
certain
uses
as
follows:

·
Pome
fruits
(
apples
and
pears):
Pesticide
products
containing
the
active
ingredient
formetanate
hydrochloride
shall
not
be
applied
after
bloom.
Late
season
applications
may
be
made
to
control
stink
bugs,
lygus
bugs,
and
pear
rust
mites
in
CA,
OR,
WA,
and
ID,
upon
written
approval
on
a
case­
by­
case
basis
by
the
State
agency
responsible
for
enforcement
of
FIFRA,
or
authorized
by
that
State
agency.

·
Peaches
and
nectarines:
Pesticide
products
containing
the
active
ingredient
formetanate
hydrochloride
shall
not
be
applied
after
shuck
fall.

·
Citrus
(
oranges,
lemons,
limes,
grapefruit,
tangelos
and
tangerines):
Pesticide
products
containing
the
active
ingredient
formetanate
hydrochloride
shall
not
be
applied
after
fruit
reach
one
inch
in
diameter.
Pesticide
products
containing
the
active
ingredient
formetanate
hydrochloride
may
be
applied
to
overcropped
grapefruits
and
Valencia
oranges
above
one
inch
in
    
3
  
38
diameter,
provided
that
a
preharvest
interval
("
PHI")
of
30
days
is
observed.

(
F)
Label
instruction
requiring
a
preharvest
interval
("
PHI")
of
21
days
for
alfalfa
(
grown
for
seed).

(
G)
Label
instructions
establishing
a
maximum
application
rate
of
not
more
than
0.92
pounds
of
active
ingredient
per
acre
on
alfalfa
grown
for
seed
only.

(
H)
Label
instructions
establishing
a
maximum
application
rate
of
not
more
than
1.15
pounds
of
active
ingredient
per
acre
for
all
food
crops.

(
I)
Label
instructions
restricting
the
replanting
of
fields
after
harvest
of
alfalfa
treated
with
pesticide
products
containing
the
active
ingredient
formetanate
hydrochloride,
as
follows:

Leafy
vegetables
shall
not
be
planted
until
30
days
after
harvest
of
treated
alfalfa.

Root
crops
shall
not
be
planted
until
120
days
after
harvest
of
treated
alfalfa.

Small
grains
and
all
other
crops
shall
not
be
planted
until
12
months
after
harvest
of
treated
alfalfa.

The
MOA
also
required
that
the
registrant
generate
certain
data
reflecting
the
new
reduced
rates
and
increased
PHIs
including
field
trials
(
OPPTS
860.1500)
for
stone
fruit,
pome
fruit,
and
citrus.
A
confirmatory
orchard
crop
(
stone
or
pome
fruit)
metabolism
study
was
also
required.
The
results
of
those
submissions
are
summarized
in
this
document.
This
document
updates
the
previous
chemistry
chapter
(
4/
97)
and
includes
only
those
uses
allowed
by
the
MOA.

The
nature
of
the
residue
of
formetanate
HCl
in
livestock
and
plants
has
been
adequately
delineated.
Formetanate
HCl
per
se
was
not
identified
in
the
ruminant
and
poultry
metabolism
studies.
The
two
cholinesterase­
inhibiting
metabolites
(
3­
formamidophenyl
methylcarbamate
and
3­
aminophenyl
methylcarbamate)
found
in
milk,
liver,
and
kidney
have
been
determined
to
be
not
of
significant
toxicological
concern
(
3/
15/
99
Metabolism
Assessment
Review
Committee,
MARC,
decision).
Therefore,
no
tolerances
are
required
for
formetanate
HCl
and
its
metabolites
for
livestock
commodities.
An
adequate
method
is
available
for
data
collection
in
livestock
commodities.
This
method
is
similar
to
Method
I
of
PAM
(
Pesticide
Analytical
Manual)
Vol.
II.
Because
tolerances
for
livestock
commodities
are
not
required,
the
registrant
is
not
required
at
this
time
to
submit
an
independent
laboratory
validation
of
this
method.

The
results
of
the
alfalfa,
lemon,
and
orange
seedling
metabolism
studies
indicate
that
the
metabolic
pathway
in
plants
is
similar
with
resulting
metabolites
containing
the
formamidine
moiety.
Formetanate
HCl
was
the
only
compound
identified
in
the
extractable
radioactivity
in/
on
peaches.
The
majority
of
the
terminal
residue
in
plants
consists
mainly
of
parent
compound.
The
majority
of
formetanate
residues
appear
on
the
surface
(
peel)
of
fruit.
Parent
formetanate
HCl
is
the
residue
of
concern
to
be
included
in
the
tolerance
expression
and
the
dietary
risk
assessment.

An
adequate
method
is
available
for
tolerance
enforcement
for
plant
commodities.
The
gas
chromatography/
electron
capture
detection
(
GC/
ECD)
Method
I
is
listed
in
the
PAM
Vol.
II
and
    
4
  
38
involves
hydrolysis
of
residues
to
3­
aminophenol
and,
therefore,
determines
residues
of
formetanate
HCl
and
all
metabolites
convertible
to
3­
aminophenol.

An
adequate
method
for
data
collection
for
plant
commodities
has
been
submitted
by
the
registrant.
The
high
performance
liquid
chromatography
(
HPLC)
method
determines
residues
of
the
parent
compound
formetanate
only.
An
independent
laboratory
validation
(
ILV)
of
the
method
was
also
submitted
and
found
adequate.
If
the
registrant
proposes
that
this
be
a
new
enforcement
method
then
the
method
should
be
radiovalidated
and
an
Agency
method
validation
should
be
performed.

Tolerances
are
established
for
residues
of
formetanate
hydrochloride
per
se
in
or
on
apple;
pear;
peach;
nectarine;
orange;
lemon;
lime;
grapefruit;
tangerine;
and
plum,
prune,
fresh
[
40CFR
180.276].
According
to
the
MOA,
the
only
food/
feed
uses
allowed
are
those
on
apple,
pear,
peach,
nectarine,
orange,
lemon,
lime,
grapefruit,
tangelo,
tangerine,
and
alfalfa
grown
for
seed.
Formetanate
HCl
tolerances
are
reassessed
in
this
document
for
the
permitted
food
uses
(
see
Table
6).
The
tolerances
were
reassessed
based
on
limited
field
trial
data
performed
at
the
reduced
rate
and
increased
PHIs.
In
general
the
field
trial
data
did
not
satisfy
the
requirements
for
number
of
field
trials
(
see
"
Residue
Chemistry
Deficiencies"
below).
At
such
time
as
the
additional
field
trials
are
received
and
deemed
adequate,
the
reassessed
tolerances
will
be
reevaluated.

Residue
Chemistry
Deficiencies
·
860.1300
Nature
of
the
Residue­
Pending
submission
of
adequate
information
regarding
the
use
of
peach
leaves
to
support
the
storage
stability
of
peach
extract,
the
requirement
for
plant
metabolism
data
for
formetanate
HCl
will
be
fulfilled.

·
860.1500
Crop
Field
Trials­
Tolerance
reassessment
will
be
reevaluated
upon
receipt
and
acceptance
of
the
following
outstanding
data:
Apple:
Four
additional
field
trials
in
Regions
1,
5,
and
11
must
be
conducted
(
the
trials
should
include
an
early
and
late
season
application
as
allowed
in
the
MOA);
Pear:
Two
additional
field
trials
in
Regions
10
and
11
must
be
conducted
(
the
trials
should
include
an
early
and
late
season
application
as
allowed
in
the
MOA);
Peach:
Three
additional
field
trials
in
Regions
1
(
or
2),
5,
and
10
must
be
submitted.
Nectarine:
Details
pertaining
to
the
field
procedures
used
in
the
at­
harvest
study
(
i.
e.,
application
method
and
timing,
equipment,
spray
volumes,
tank
mix
adjuvants)
and
multiple
application
rates
must
be
provided.;
Citrus
Fruit:
Five
additional
orange
field
trials
in
Regions
6
and
10
must
be
conducted.
An
additional
lemon
trial
(
Region
10)
and
2
additional
grapefruit
trials
(
Regions
6,
10)
are
also
required.
    
5
  
38
Chemical
Overview
TABLE
1.
Test
Compound
Nomenclature
Compound
Chemical
Structure
Common
name
Formetanate
HCl
Company
experimental
name
Carzol
®

IUPAC
name
3­
dimethylaminomethyleneaminophenyl
methylcarbamate
monohydrochloride
CAS
name
Methanimidamide,
N,
N­
dimethyl­
N ­[
3­[[(
methylamino)
carbonyl]
oxy]
phenyl]­,
monohydrochloride
CAS
#
23422­
53­
9
TABLE
2.
Physicochemical
Properties
1
Parameter
Value
Melting
point/
range
191.2
C
pH
 
2.5
(
10%
solution)

Density
200­
450
g/
L
Water
solubility
(
25
°
C)
82.2
g/
100mL
Solvent
solubility
(
g/
100mL
at
20
°
C)
n­
hexane
<
0.00005
ethylacetate
0.0001
toluene
0.001
acetone
0.007
dichloromethane
0.03
methanol
28.3
Vapor
pressure
at
25
°
C
1.6
x
10­
6
mmHg
Dissociation
constant
(
pKa)
8.0
Octanol/
water
partition
coefficient
(
KOW)
<
0.002
UV/
visible
absorption
spectrum
2
 
max:
Molar
Absorbance
Absorbance
Media
Maximum
Coefficient
Acidic
208
nm
22130
250
nm
16603
Neutral
208
nm
21934
250
nm
16540
Basic
236
nm
23015
Results
indicate
no
significant
change
in
absorption
in
acidic
and
neutral
media;
however,
a
significant
change
in
the
wavelength
maximum
was
observed
in
basic
media.

1
Information
collected
from
a
92%
technical
product
or
from
D173714,
8/
26/
92,
W.
Smith.
2
Information
collected
from
D270875,11/
7/
02,
D.
Drew.
    
6
  
38
860.1200
Directions
for
Use
An
OPPIN
search
conducted
on
12/
14/
05
identified
one
formetanate
HCl
end­
use
product
(
EP)
registered
to
Gowan
Co.
for
use
on
food/
feed
crops
(
Table
3).
There
are
two
Special
Local
Need
(
SLN)
registrations
under
FIFRA
Section
24.

HED
has
examined
the
registered
food/
feed
use
patterns
and
reevaluated
the
available
residue
chemistry
database
for
adequacy
in
supporting
these
use
patterns.
A
comprehensive
summary
of
formetanate
HCl
food/
feed
use
patterns,
based
on
the
product
labels
registered
to
Gowan,
is
presented
in
Table
4.
The
status
of
reregistration
requirements
for
each
guideline
topic
listed
in
Table
7
is
based
on
the
use
patterns
registered
by
the
basic
producer.
When
end­
use
product
DCIs
are
developed
(
e.
g.,
at
issuance
of
the
RED),
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.

The
registered
use
of
formetanate
HCl
on
alfalfa
grown
for
seed
in
CA,
ID,
NV,
OR,
WA
and
AZ
is
considered
to
be
a
non­
food
use,
since
these
states
have
established
programs
designed
to
prevent
diversion
of
alfalfa
forage,
hay,
seed,
and
seed
screenings
(
from
treated
alfalfa
grown
for
seed)
to
livestock
feed.

Table
3.
Formetanate
HCl
EP
with
Food/
Feed
Uses
Registered
to
Gowan
EPA
Reg.
No.
Label
Acceptance
Date
Formulation
Product
Name
10163­
2651
7/
23/
02
92%
WP
Carzol
®
SP
in
Water
Soluble
Packaging
Miticide/
Insecticide
1
Including
SLNs
AZ030012,
ID030016
(
alfalfa
for
seed
[
non­
food
use])
TABLE
4
(
Formerly
Table
A2)
FOOD/
FEED
USE
PATTERNS
SUMMARY
FOR
Formetanate
hydrochloride
(
CASE
0091)
    
7
  
38
SITE
NAME
Product/
Site
Limitations
Application
Type
(
for
any
Reg.#
at
any
rate)
(
aggregate)
Application
Timing
(
for
any
Reg.#
at
any
rate)
Application
Equipment
(
for
any
Reg.#
at
any
rate)

(
aggregate)
Max.
Single
Appl.

Rate
to
a
Single
Site
(
AI
unless
notedotherwise)
InconvertibleLabel
(
L)
DosagesAlso
Present
MaxSeaso
nalRate
(
L)
Dosage
sAlsoPres
ent
Max.
#

Apps
Per
Crop
Cycle
(
cc)
and
Year
(
at
any
rate)
Min
Retmt
Intv
(
days)

(
at
any
rate)
PHI/
PGI/
PSIUse
Limitations
(
at
any
rate)

(
May
not
apply
to
all
Reg.
#
s
within
group)

ALFALFA
21
day(
s)
preharvest
interval.
Do
not
apply
through
any
type
of
irrigation
system.
Do
not
contaminate
water,
food
or
feed.

Do
not
contaminate
water,
food,
or
feed
by
storage
or
disposal.
Do
not
feed
to
livestock.
Do
not
graze
livestock
in
treated
areas.

Do
not
graze
livestock
in
treated
orchards.
Do
not
graze
or
feed
treated
crop
to
livestock.
For
terrestrial
uses,
do
not
apply
directly
to
water
or
to
areas
where
surface
water
is
present
or
to
intertidal
areas
below
the
mean
high
water
mark.

Formulation
is
contained
within
water
soluble
bags.
Grown
for
seed
only.

Rotational/
plant
back
crop
restriction.

Geographic
allowable:
AZ
CA
ID
NV
OR
WAGeographic
disallowable:
FL
A
second
application
(
post­
bloom)
may
be
made
to
control
lygus
bugs
in
AZ
and
ID.

Low
volume
spray
(
concentrate)/
Spray
FoliarAircraft/
Ground
.92
lb
A
1.84
lb/
cc
2/
ccNS
NS
Low
volume
spray
(
concentrate)/
Spray
PrebloomAircraft/
Ground
.92
lb
A
.92
lb/
cc
1/
ccNS
NS
Geographic
disallowable:
CA
APPLE
Do
not
apply
after
petal
fall.
Do
not
apply
through
any
type
of
irrigation
system.
Do
not
contaminate
water,
food,
or
feed
by
storage
or
disposal.

Do
not
graze
livestock
in
treated
orchards.
For
terrestrial
uses,

do
not
apply
directly
to
water
or
to
areas
where
surface
water
is
present
or
to
intertidal
areas
below
the
mean
high
water
mark.
Formulation
is
contained
within
water
soluble
bags.

[
A
second,
later
season,
application
may
be
made
to
control
stink
bugs,
lygus
bugs,
and
pear
rust
mites
in
CA,
OR,
WA,
and
ID
only
after
written
approval
by
the
State
agency
responsible
for
enforcement
of
FIFRAor
authorized
by
that
State
agency.
]

Geographic
disallowable:
FL
High
volume
spray
(
dilute)/
Low
volume
spray
(
concentrate)
BloomHigh
volume
ground
sprayer/
Low
volume
sprayer
1.15
lb
A
1.15
lb/
cc
2/
ccNS
NS
High
volume
spray
(
dilute)/
Low
volume
spray
(
concentrate)
FoliarHigh
volume
ground
sprayer/
Low
volume
sprayer
1.15
lb
A
1.15
lb/
cc
2/
ccNS
NS
Spray
Petal
fall
through
foliarSprayer
1.15
lb
A
NS
1/
ccNS
NS
Geographic
allowable:
WA
Late
Season
application
TABLE
4
(
Formerly
Table
A2)
FOOD/
FEED
USE
PATTERNS
SUMMARY
FOR
Formetanate
hydrochloride
(
CASE
0091)
    
8
  
38
High
volume
spray
(
dilute)/
Low
volume
spray
(
concentrate)
Petal
fallHigh
volume
ground
sprayer/
Low
volume
sprayer
1.15
lb
A
1.15
lb/
cc
2/
ccNS
NS
High
volume
spray
(
dilute)/
Low
volume
spray
(
concentrate)
PinkHigh
volume
ground
sprayer/
Low
volume
sprayer
1.15
lb
A
1.15
lb/
cc
2/
ccNS
NS
High
volume
spray
(
dilute)/
Low
volume
spray
(
concentrate)

PrebloomAircraft/
High
volume
ground
sprayer/
Low
volume
sprayer
.92
lb
A
1.15
lb/
cc
2/
ccNS
NS
(
Geographic
disallowable:

CA
,

for
campylomma
control)

Spray
When
neededAircraft/
Ground
1.15
lb
A
NS
NSNS
NS
GRAPEFRUIT
Do
not
apply
through
any
type
of
irrigation
system.
Do
not
contaminate
water,

food,
or
feed
by
storage
or
disposal.
Do
not
graze
livestock
in
treated
orchards.

For
terrestrial
uses,
do
not
apply
directly
to
water
or
to
areas
where
surface
water
is
present
or
to
intertidal
areas
below
the
mean
high
water
mark.
Formulation
is
contained
within
water
soluble
bags.
Do
not
apply
after
fruit
reach
a
diameter
of
one
inch.

If
unharvested
grapefruit
and
Valencia
oranges
are
present
from
the
previous
crop,
an
application
may
be
made
to
the
new
crop.
A
preharvest
interval
of
30
days
must
be
observed
for
the
unharvested
crop.
Geographic
disallowable:
FL
High
volume
spray
(
dilute)/
Spray
FoliarAircraft/
High
volume
ground
sprayer/
Sprayer
1.15
lb
A
1.15
lb/
cc
1/
ccNS
NS
30
day(
s)
preharvest
interval.

Geographic
allowable:
AZ
CA
TX
LEMON
Do
not
apply
through
any
type
of
irrigation
system.
Do
not
contaminate
water,

food,
or
feed
by
storage
or
disposal.
Do
not
graze
livestock
in
treated
orchards.

For
terrestrial
uses,
do
not
apply
directly
to
water
or
to
areas
where
surface
water
is
present
or
to
intertidal
areas
below
the
mean
high
water
mark.
Formulation
is
contained
within
water
soluble
bags.
Do
not
apply
after
fruit
reach
a
diameter
of
one
inch.
Geographic
disallowable:
FL
Broadcast/
High
volume
spray
(
dilute)/
Low
volume
spray
(
concentrate)/
Spray
FoliarAircraft/
High
volume
ground
sprayer/
Sprayer
1.15
lb
A
1.15
lb/
cc
1/
ccNS
NS
60
day(
s)
preharvest
interval.

Geographic
allowable:
AZ
CA
TX
LIME
Do
not
apply
through
any
type
of
irrigation
system.
Do
not
contaminate
water,

food,
or
feed
by
storage
or
disposal.
Do
not
graze
livestock
in
treated
orchards.

For
terrestrial
uses,
do
not
apply
directly
to
water
or
to
areas
where
surface
water
is
present
or
to
intertidal
areas
below
the
mean
high
water
mark.
Formulation
is
contained
within
water
soluble
bags.
Do
not
apply
after
fruit
reach
a
diameter
of
one
inch
Geographic
disallowable:
FL
Spray
FoliarAircraft/
Sprayer
1.15
lb
A
1.15
lb/
cc
1/
ccNS
NS
Geographic
allowable:
CA
TABLE
4
(
Formerly
Table
A2)
FOOD/
FEED
USE
PATTERNS
SUMMARY
FOR
Formetanate
hydrochloride
(
CASE
0091)
    
9
  
38
NECTARINE
Do
not
apply
after
petal
fall.
Do
not
apply
through
any
type
of
irrigation
system.
Do
not
contaminate
water,
food,
or
feed
by
storage
or
disposal.

Do
not
graze
livestock
in
treated
orchards.
For
terrestrial
uses,

do
not
apply
directly
to
water
or
to
areas
where
surface
water
is
present
or
to
intertidal
areas
below
the
mean
high
water
mark.
Formulation
is
contained
within
water
soluble
bags.

Geographic
disallowable:
FL
High
volume
spray
(
dilute)/
Low
volume
spray
(
concentrate)

BloomAircraft/
High
volume
ground
sprayer/
Low
volume
sprayer
1.15
lb
A
1.15
lb/
cc
1/
ccNS
NS
High
volume
spray
(
dilute)/
Low
volume
spray
(
concentrate)
Petal
fallAircraft/
High
volume
ground
sprayer/
Low
volume
sprayer
1.15
lb
A
1.15
lb/
cc
1/
ccNS
NS
ORANGE
Do
not
apply
through
any
type
of
irrigation
system.
Do
not
contaminate
water,

food,
or
feed
by
storage
or
disposal.
Do
not
graze
livestock
in
treated
orchards.

For
terrestrial
uses,
do
not
apply
directly
to
water
or
to
areas
where
surface
water
is
present
or
to
intertidal
areas
below
the
mean
high
water
mark.
Formulation
is
contained
within
water
soluble
bags.
Do
not
apply
after
fruit
reach
a
diameter
of
one
inch.
If
unharvested
grapefruit
and
Valencia
oranges
are
present
from
the
previous
crop,
an
application
may
be
made
to
the
new
crop.
A
preharvest
interval
of
30
days
must
be
oserved
for
the
unharvested
crop.
Geographic
disallowable:
FL
High
volume
spray
(
dilute)/
Spray
FoliarAircraft/
High
volume
ground
sprayer/
Sprayer
1.15
lb
A
1.15
lb/
cc
1/
ccNS
NS
30
day(
s)
preharvest
interval.

Geographic
allowable:
AZ
CA
TX
PEACH
Do
not
apply
after
petal
fall.
Do
not
apply
through
any
type
of
irrigation
system.
Do
not
contaminate
water,
food,
or
feed
by
storage
or
disposal.

Do
not
graze
livestock
in
treated
orchards.
For
terrestrial
uses,

do
not
apply
directly
to
water
or
to
areas
where
surface
water
is
present
or
to
intertidal
areas
below
the
mean
high
water
mark.
Formulation
is
contained
within
water
soluble
bags.

Geographic
disallowable:
FL
High
volume
spray
(
dilute)/
Low
volume
spray
(
concentrate)
Petal
FallHigh
volume
ground
sprayer/
Low
volume
sprayer
1.15
lb
A
1.15
lb/
cc
1/
ccNS
NS
PEAR
Do
not
apply
after
petal
fall.
Do
not
apply
through
any
type
of
irrigation
system.
Do
not
contaminate
water,
food,
or
feed
by
storage
or
disposal.

Do
not
graze
livestock
in
treated
orchards.
For
terrestrial
uses,

do
not
apply
directly
to
water
or
to
areas
where
surface
water
is
present
or
to
intertidal
areas
below
the
mean
high
water
mark.
Formulation
is
contained
within
water
soluble
bags.

[
A
second,
later
season,
application
may
be
made
to
control
stink
bugs,
lygus
bugs,
and
pear
rust
mites
in
CA,
OR,
WA,
and
ID
only
after
written
approval
by
the
State
agency
responsible
for
enforcement
of
FIFRAor
authorized
by
that
State
agency.
]

Geographic
disallowable:
FL
High
volume
spray
(
dilute)/
Low
volume
spray
(
concentrate)
FoliarHigh
1.15
lb
A
1.15
NSNS
NS
TABLE
4
(
Formerly
Table
A2)
FOOD/
FEED
USE
PATTERNS
SUMMARY
FOR
Formetanate
hydrochloride
(
CASE
0091)
    
10
  
38
volume
ground
sprayer/
Low
volume
sprayer
lb/
cc
Spray
Petal
fall
through
foliarSprayer
1.15
lb
A
NS
1/
ccNS
NS
Spray
PostharvestSprayer
1.15
lb
A
NS
1/
ccNS
NS
Geographic
allowable:
WA
TABLE
4
(
Formerly
Table
A2)
FOOD/
FEED
USE
PATTERNS
SUMMARY
FOR
Formetanate
hydrochloride
(
CASE
0091)

11
Spray
When
neededGround
1.15
lb
A
NS
NSNS
NS
TANGELO
D
o
not
apply
through
any
type
of
irrigation
system.
food,
or
feed
by
storage
or
disposal.
Do
not
gra
For
terrestrial
uses,
do
not
apply
directly
to
wa
present
or
to
intertidal
areas
below
the
mean
high
water
mark.
within
water
soluble
bags.
Do
not
appl
inch.
Geographic
disallowabl
Spray
FoliarAircraft/
Sprayer
1.15
lb
A
1.15
lb/
cc
1/
ccNS
NS
G
TANGERINES
Do
not
apply
through
any
type
of
irrigation
system.
food,
or
feed
by
storage
or
disposal.
Do
not
gra
For
terrestrial
uses,
do
not
apply
directly
to
wa
present
or
to
intertidal
areas
below
the
mean
high
water
mark.
within
water
soluble
bags.
Do
not
appl
inch.
Geographic
disallowable:
FL
High
volume
spray
(
dilute)/
Spray
FoliarAircraft/
High
volume
ground
sprayer/
Sprayer
1.15
lb
A
1.15
lb/
cc
1/
ccNS
NS
G
Product
Number(
s)
Contained
in
this
Report
:
010163­
00265
;
AZ030012,
ID030016
860.1300
Nature
of
the
Residue
­
Plants
Tolerances
are
established
for
residues
of
formetanate
hydrochloride
per
se
in
or
on
apple;
pear;
peach;
nectarine;
orange;
lemon;
lime;
grapefruit;
tangerine;
and
plum,
prune,
fresh
[
40CFR
180.276].
According
to
the
10/
99
MOA,
the
only
food/
feed
uses
allowed
are
those
on
apples,
pears,
peaches,
nectarines,
oranges,
lemons,
limes,
grapefruit,
tangelos,
tangerines,
and
alfalfa
grown
for
seed.

The
qualitative
nature
of
the
residue
in
alfalfa
is
adequately
understood;
the
majority
of
the
terminal
residue
in
alfalfa
forage
consists
mainly
of
parent
compound
and
related
compounds
containing
the
3­
aminophenol
moiety.

A
lemon
study
(
MRID
42684605)
was
deemed
inadequate
because
the
test
substance
was
not
    
12
  
38
applied
foliarly,
and
therefore
the
resulting
metabolic
profile
did
not
take
into
account
metabolites
resulting
from
translocation.
In
addition,
the
total
radioactive
residue
(
TRR)
was
not
properly
determined
in
the
whole
fruit.
The
lemon
metabolism
study
indicated
that
parent
formetanate
was
the
major
residue
and
metabolites
were
identified
as
3­
dimethylaminomethylenaminophenol,
3­
formaminophenyl
 
methyl­
carbamate
(
SN35902),
and
3­
formaminophenol
(
SN38075)
(
D189020,
C.
Swartz,
1/
3/
97).
The
MARC
determined
that
SN35902
and
SN38075
were
not
of
toxicological
concern
as
they
are
86
and
48
times,
respectively,
less
potent
as
cholinesterase
inhibitors
than
parent
formetanate
(
3/
15/
99
MARC).

A
literature
study
on
orange
seedlings
also
shows
that
the
metabolic
pathway
in
plants
proceeds
primarily
by
hydrolysis
to
SN35902
(
major
metabolite,
11%
TRR)
and
SN38075
and
related
conjugates.
The
phenol
(
SN38075)
is
deformylated
to
3­
aminophenol
and
acelylated
to
3­
acetamidophenol
(
Roberts,
Terry,
and
David
Hudson,(
editors).
Metabolic
Pathways
of
Agrochemicals,
Part
2:
Insecticides
and
Fungicides,
Cambridge:
The
Royal
Society
of
Chemistry,
1999).

Gowan
Company
submitted
a
study
investigating
the
metabolism
of
[
14C]
formetanate
hydrochloride
in
peach
as
a
result
of
the
10/
99
MOA
(
MRID
45595601).
Radiolabeled
[
14C]
formetanate
HCl,
uniformly
labeled
in
the
phenyl
ring,
was
applied
to
two
separate
branches
of
a
peach
tree
at
rates
equivalent
to
1.15
lb
ai/
A
(
1x
rate)
and
11.5
lb
ai/
A
(
10x
rate).
Samples
of
peach
leaves
were
harvested
on
the
day
of
treatment,
and
samples
of
immature
and
mature
fruit
were
collected
from
each
branch
at
33
and
91
days
posttreatment,
respectively.

TRR
were
determined
in
samples
of
peach
leaves
and
immature
peaches
by
summing
radioactivity
in
the
extracts
and
the
nonextractable
radioactivity.
TRR
in
mature
peaches
were
determined
by
combustion/
LSC.
Samples
of
leaves
were
rinsed
with
0.1%
HCl
to
extract
radioactivity.
Samples
of
immature
peaches
were
rinsed
and
then
extracted
with
0.1%
HCl,
and
samples
of
mature
peaches
were
extracted
with
0.1%
HCl.
The
aqueous
extracts
of
peach
leaves
(
both
treatment
rates)
and
immature
and
mature
peaches
(
10x
rate
only)
were
analyzed
by
HPLC.
Peach
leaf
extracts
were
also
analyzed
by
thin
layer
chromatography
(
TLC).

Following
treatment
of
a
branch
of
a
peach
tree
with
[
14C]
formetanate
HCl
at
10X
rate
(
11.5
lb
ai/
A),
TRR
were
112­
187
ppm
in/
on
peach
leaves
harvested
0
days
posttreatment,
0.014­
0.026
ppm
in/
on
immature
peaches
harvested
33
days
posttreatment,
and
0.004­
0.008
ppm
in/
on
mature
peaches
harvested
91
days
posttreatment.
Approximately
87­
92%
of
TRR
were
extractable
from
peach
leaves,
and
approximately
48­
77%
of
TRR
were
extractable
from
immature
and
mature
peaches.
Only
extracts
of
peach
leaves
from
this
treatment
rate
were
analyzed.
Formetanate
HCl
was
identified
at
80.2­
85.3%
TRR;
the
remainder
of
the
aqueous
extractable
radioactivity
consisted
of
unknowns,
each
of
which
was
present
at
 
5.2%
TRR.

Following
treatment
of
a
branch
of
a
peach
tree
with
[
14C]
formetanate
HCl
at
11.5
lb
ai/
A,
TRR
were
594­
1130
ppm
in/
on
peach
leaves
harvested
0
days
posttreatment,
0.170­
0.233
ppm
in/
on
immature
peaches
harvested
33
days
posttreatment,
and
0.033­
0.110
ppm
in/
on
mature
peaches
harvested
91
days
posttreatment.
Approximately
93­
95%
of
TRR
were
extractable
from
peach
leaves,
and
approximately
72­
76%
of
TRR
were
extractable
from
immature
and
mature
peaches.
Formetanate
HCl
was
the
only
compound
identified
in
the
extractable
radioactivity,
at
86.4­
89.4%
TRR
(
514­
1000
ppm)
in/
on
peach
leaves,
49%
TRR
(
0.115
ppm)
in/
on
immature
peaches,
and
47%
TRR
(
0.052
ppm)
in/
on
mature
peaches.
The
remainder
of
the
aqueous
extractable
radioactivity
consisted
of
unknowns,
each
of
which
was
present
at
 
7.4%
TRR.

This
study
did
not
attempt
to
extract
or
determine
organic
activity
or
bound
residues;
only
an
    
13
  
38
aqueous
HCl
extraction
was
performed,
yielding
72%
(
0.079
ppm)
TRR
on
mature
peaches.
The
remaining
0.031
ppm
(
28%)
TRR
were
labeled
as
"
nonextractable."
Nonetheless,
the
majority
of
the
TRR
in/
on
peaches
are
identified
as
parent
and
the
unknowns
are
less
than
0.008
ppm.
Also,
the
results
of
the
alfalfa,
lemon,
and
orange
seedling
studies
indicate
that
the
metabolic
pathway
in
plants
is
similar
with
resulting
metabolites
containing
the
formamidine
moiety.
Based
on
that
information
and
that
the
enforcement
method
is
a
common
moiety
method
(
all
metabolites
converted
to
3­
aminophenol),
additional
data
on
the
metabolism
of
formetanate
residues
on
peaches
are
not
required
at
this
time;
however,
the
peach
study
is
inadequate
to
satisfy
data
requirements
for
a
plant
metabolism
study
with
peach
because
additional
data
are
required
pertaining
to
storage
stability.
The
registrant
should
provide
supporting
chromatographic
evidence
for
their
statement
that
a
day­
0
leaf
extract
was
found
to
be
stable
for
13
months,
and
justification
for
use
of
a
day­
0
leaf
extract
to
support
the
storage
of
an
extract
of
peach
fruit
for
up
to
9
months
prior
to
analysis.

Pending
submission
of
adequate
information
regarding
the
use
peach
leaves
to
support
the
storage
stability
of
peach
extract,
the
requirement
for
plant
metabolism
data
for
formetanate
HCl
will
be
fulfilled.

860.1300
Nature
of
the
Residue
­
Livestock
The
reregistration
data
requirement
for
livestock
metabolism
is
fulfilled.
Acceptable
studies
depicting
the
qualitative
nature
of
the
residue
in
ruminants
and
poultry
have
been
submitted.
Formetanate
hydrochloride
per
se
was
not
identified
in
the
metabolism
studies.
The
two
cholinesterase­
inhibiting
metabolites
(
3­
formamidophenyl
methylcarbamate
and
3­
aminophenyl
methylcarbamate)
found
in
milk,
liver,
and
kidney
have
been
determined
to
be
not
of
significant
toxicological
concern.
Therefore,
no
tolerances
are
required
for
formetanate
hydrochloride
and
its
metabolites
for
livestock
commodities
(
3/
15/
99
MARC).

860.1340
Residue
Analytical
Methods
Adequate
methods
are
available
for
data
collection
and
tolerance
enforcement
for
plant
commodities.
A
GC/
ECD
method
(
Method
I)
is
listed
in
the
PAM
Vol.
II
for
the
enforcement
of
formetanate
hydrochloride
tolerances
in
fruits.
This
method
involves
hydrolysis
of
residues
to
3­
aminophenol
and,
therefore,
determines
residues
of
formetanate
and
all
metabolites
convertible
to
3­
aminophenol.
Methods
A
and
A(
1)
are
two
TLC­
colorimetric
methods
deemed
adequate
for
data
collection
for
the
respective
purposes
of
formetanate
hydrochloride
residue
confirmation
and
determination
of
formetanate
hydrochloride
hydrolysis
products.

An
adequate
method
for
data
collection
for
plant
commodities
has
been
submitted
by
the
registrant.
The
HPLC
method
determines
residues
of
the
parent
formetanate
only.
An
ILV
of
the
method
was
also
submittted
and
found
adequate.
If
the
registrant
proposes
that
this
be
a
new
enforcement
method,
the
method
should
be
radiovalidated
and
an
Agency
method
validation
should
be
performed.

An
adequate
method
is
available
for
data
collection
in
livestock
commodities.
This
method
is
similar
to
Method
I
of
PAM
Vol.
II,
but
includes
an
additional
acid
hydrolysis
step
to
release
bound
residues.
Because
tolerances
for
livestock
commodities
are
not
required,
the
registrant
is
not
required
at
this
time
to
submit
an
ILV
of
this
method.
    
14
  
38
860.1360
Multiresidue
Methods
The
January
1994
FDA
PESTDATA
database
(
PAM
Volume
I,
Appendix
I,
10/
99
update)
has
no
information
pertaining
to
the
recovery
of
formetanate
HCl
through
multiresidue
methods
(
MRMs).
The
registrant
attempted
to
conduct
methods
trials
with
formetanate
HCl
(
Protocols
A
through
E)
but
these
submissions
did
not
provide
information
regarding
recoveries
via
FDA's
MRMs.
This
is
not
a
deficiency
as
water­
soluble
formetanate
HCl
would
not
be
expected
to
extract
efficiently
via
FDA's
MRMs.

860.1380
Storage
Stability
The
reregistration
requirements
for
storage
stability
data
are
fulfilled.
The
available
storage
stability
data
indicate
that
formetanate
residues
are
generally
stable
in
frozen
apples
and
stone
fruits
for
up
to
33
months,
and
in
frozen
citrus
fruits
for
up
to
2
years.
Residues
of
the
metabolite
3­
formamidophenyl­
N­
methylcarbamate
declined
after
storage
intervals
of
9
to
33
months.
This
metabolite
is
considered
not
of
significant
toxicological
concern.
Storage
stability
data
support
the
storage
intervals
used
in
the
field
trial
studies.

860.1400
Water,
Fish,
and
Irrigated
Crops
Formetanate
hydrochloride
is
not
presently
registered
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
Formetanate
hydrochloride
is
not
presently
registered
for
use
in
food­
handling
establishments,
therefore;
no
residue
chemistry
data
are
required
under
this
guideline
topic.

860.1480
Meat,
Milk,
Poultry,
and
Eggs
Adequate
livestock
feeding
studies
have
been
submitted
to
the
Agency.
The
reregistration
requirements
for
magnitude
of
the
residue
in
meat,
milk,
poultry,
and
eggs
are
fulfilled.

Milk
and
the
fat,
meat,
and
meat
byproducts
of
cattle,
goats,
hogs,
horses,
and
sheep:
The
maximum
theoretical
dietary
burdens
of
formetanate
HCl
to
beef
and
dairy
cattle
are
1.5
ppm
and
0.75
ppm,
respectively,
based
on
a
diet
consisting
of
wet
apple
pomace
(
40%
and
20%,
respectively,
of
the
diet).
An
adequate
dairy
cattle
feeding
study
has
been
submitted;
the
study
reflected
dosing
with
formetanate
HCl
~
20,
60,
and
200
ppm
for
28­
31
days.
These
dosing
levels
represent
13X,
40X,
and
130X
the
maximum
theoretical
dietary
burden
to
beef
cattle
and
27X,
80X,
and
270X
the
maximum
theoretical
dietary
burden
to
dairy
cattle.

No
detectable
residues
of
parent
formetanate
were
observed
in
milk,
fat,
muscle,
kidney,
and
liver.
The
two
cholinesterase­
inhibiting
metabolites
(
3­
formamidophenyl
methylcarbamate
[
SN
35902]
and
3­
aminophenyl
methylcarbamate
[
SN
38075])
found
in
dairy
milk,
liver,
and
kidney
have
been
determined
to
be
not
of
significant
toxicological
concern
as
a
result
of
an
in
vitro
study.
The
study
found
that
these
metabolites
were
86
and
48
times
less
potent
as
cholinesterase
inhibitors
than
parent
formetanate.
These
findings,
along
with
the
fact
that
these
two
metabolites
    
15
  
38
are
found
in
rats
and
thus
their
toxicity
is
assessed
when
the
parent
compound
is
assessed,
indicate
that
the
tolerance
expression
does
not
need
to
include
these
metabolites
(
J.
Doherty,
12/
10/
98,
DP:
D249197;
MARC
Decisions
1/
12/
99,
D252123
and
3/
15/
99,
D254395).
Therefore,
no
tolerances
are
required
for
formetanate
hydrochloride
and
its
metabolites
for
milk
and
the
fat,
meat,
and
meat
byproducts
of
cattle,
goats,
horses,
and
sheep
(
40CFR
180.6(
a)(
3)).

A
2/
19/
97
HED
metabolism
committee
decision
determined
that
for
purposes
of
risk
assessment,
only
the
potentially
cholinesterase­
inhibiting
metabolites
(
3­
formamidophenyl
methylcarbamate
and
3­
aminophenyl
methylcarbamate)
should
be
considered
for
livestock
commodities.
These
metabolites
were
found
in
dairy
milk,
liver,
and
kidney
at
combined
levels
of
0.012
ppm,
0.018
ppm,
and
0.055
ppm,
respectively,
using
a
100x
feeding
rate.
Since
these
two
metabolites
have
been
determined
as
not
of
significant
toxicological
concern,
milk
and
the
fat,
meat,
and
meat
byproducts
of
cattle,
goats,
horses,
and
sheep
do
not
need
to
be
included
in
the
dietary
risk
assessment
for
formetanate
HCl.

Fat,
meat,
and
meat
byproducts
of
hogs:
No
tolerances
are
required
for
the
fat,
meat,
and
meat
byproducts
of
hogs
because
there
are
no
registered
uses
of
formetanate
hydrochloride
on
any
swine
feed
item.

Eggs
and
the
fat,
meat,
and
meat
byproducts
of
poultry:
Currently,
there
are
no
registered
uses
of
formetanate
hydrochloride
on
any
poultry
feed
item,
and
there
are
no
registered
direct
animal
treatments
of
formetanate
hydrochloride
to
poultry;
therefore,
no
residue
chemistry
data
are
required
for
poultry
commodities.

860.1500
Crop
Field
Trials
Tolerances
are
established
for
residues
of
formetanate
hydrochloride
per
se
in
or
on
apple;
pear;
peach;
nectarine;
orange;
lemon;
lime;
grapefruit;
tangerine;
and
plum,
prune,
fresh
[
40CFR
180.276].
According
to
the
10/
99
MOA,
the
only
food/
feed
uses
allowed
are
those
on
apple,
pear,
peach,
nectarine,
orange,
lemon,
lime,
grapefruit,
tangelo,
tangerine,
and
alfalfa
grown
for
seed.

Limited
residue
data
are
available
to
support
uses
on
apple,
pear,
peach,
nectarine
orange,
lemon,
lime,
grapefruit,
tangelo
and
tangerine
at
the
MOA
maximum
application
rate
of
1.15
lb
a.
i./
A.
The
registrant
submitted
field
trial
studies
at
the
new
reduced
rate
for
apple,
pear,
peach,
nectarine,
orange,
grapefruit
and
lemon.
The
number
of
trials
for
these
studies
were
determined
to
be
inadequate.

Field
trial
data
are
no
longer
required
for
alfalfa
commodities
since
the
use
on
alfalfa
grown
for
seed
in
CA,
ID,
NV,
OR,
WA
and
AZ
is
considered
to
be
a
non­
food
use.

Table
5.
Summary
of
Residues
from
the
Crop
Field
Trials
with
Formetanate
HCl
Formetanate
only
(
HPLC
method)
Residues
(
ppm)
Formetanate
and
Metabolites
(
GC/
ECD
common
moeity
method)
Residues
(
ppm)
Crop
Matrix
App.
Rate
(
lb
ai/
A)
PHI
(
days)

Mean
HAFT
Min.
Max.
Mean
HAFT
Min.
Max.

Pear
and
Apple
(
label
rate
=
1.15
lb
ai/
A
lb
ai/
A
total
application
rate,
not
to
be
applied
after
petal
fall1)

Pear
1.15
~
120
0.015
<
0.030
<
0.030
<
0.030
0.010
<
0.020
<
0.020
<
0.020
Apple
1.15
~
120
0.015
<
0.030
<
0.030
<
0.030
0.014
<
0.022
<
0.020
0.024
    
16
  
38
Apple
2.30
14
0.38
0.38
0.34
0.43
0.26
0.26
0.24
0.28
Peach
and
Nectarine
(
label
rate
=
1.15
lb
ai/
A
lb
ai/
A
total
application
rate,
not
to
be
applied
after
shuck
fall)

Peach
1.15
57­
124
0.015
<
0.030
<
0.030
<
0.030
0.010
<
0.020
<
0.020
<
0.020
Nectarine
0.9­
1.12
87­
116
0.05
<
0.10
<
0.10
<
0.10
0.056
0.25
<
0.020
0.29
Citrus2
(
label
rate
=
1.15
lb
ai/
A
lb
ai/
A
total
application
rate,
not
to
be
applied
to
fruit
>
1"
in
diameter)
3
Grapefruit
1.15
215
0.015
<
0.030
<
0.030
<
0.030
0.010
<
0.020
<
0.020
<
0.020
Grapefruit
(
overcrop)
1.15
42
0.060
0.060
0.061
0.059
0.042
0.042
0.031
0.054
Grapefruit
(
overcrop)
1.15
30
0.054
0.054
0.048
0.060
0.070
0.070
0.058
0.081
Lemon
1.15
207
0.015
<
0.030
<
0.030
<
0.030
0.010
<
0.020
<
0.020
<
0.020
Lemon
(
overcrop)
1.15
42
0.46
0.46
0.44
0.48
0.50
0.50
0.47
0.54
Lemon
(
overcrop)
1.15
30
0.98
0.98
0.87
1.1
0.98
0.98
0.95
1.1
Orange
1.15
269
0.015
<
0.030
<
0.030
<
0.030
0.016
0.022
<
0.020
0.023
Orange
(
overcrop)
1.15
42
0.20
0.20
0.19
0.20
0.31
0.31
0.42
0.20
Orange
(
overcrop)
1.15
30
0.28
0.28
0.23
0.34
0.45
0.45
0.40
0.50
1
One
additional
late
season
application
may
be
made
pears
and
apples
to
control
stink
bugs,
lygus
bugs,
and
pear
rust
mites
in
CA,
OR,
WA,
and
ID,
upon
written
approval
on
a
case­
by­
case
basis
by
the
State
agency
responsible
for
enforcement
of
FIFRA,
or
authorized
by
that
State
agency.
No
PHI
is
specified
but
a
16
day
REI
(
re­
entry
interval)
applies
to
hand
harvesting
fruit.
2
may
be
applied
to
oranges,
lemons,
limes,
grapefruit,
tangelos,
tangerines.
3
May
be
applied
to
overcropped
grapefruit
and
Valencia
oranges
>
1"
provided
a
30
day
PHI
is
observed.
May
be
applied
to
lemons
>
1"
provided
a
60
day
PHI
is
observed.

APPLE
,
PEAR
According
to
the
10/
99
MOA,
the
specific
requirements
for
continued
use
of
formetanate
hydrochloride
on
apples
and
pears
include
label
revision
to
specify
that
the
pesticide
shall
not
be
applied
after
bloom
(
petal
fall)
along
with
a
maximum
application
rate
of
not
more
than
1.15
lb
ai/
A
(
1.25
lb
Carzol
®
SP)
for
all
food
crops.
One
additional
late
season
application
may
be
made
to
control
stink
bugs,
lygus
bugs,
and
pear
rust
mites
in
CA,
OR,
WA,
and
ID,
upon
written
approval
on
a
case­
by­
case
basis
by
the
State
agency
responsible
for
enforcement
of
FIFRA,
or
authorized
by
that
State
agency.

Prior
to
the
submission
of
the
apple
and
pear
studies
(
MRIDs
45485001
and
45485002),
HED
reviewed
a
protocol
for
the
conduct
of
apple,
pear
,
peach,
orange,
lemon
and
grapefruit
field
trials
(
DP
Barcode
D263912,
3/
15/
00,
D.
Drew).
In
the
submitted
protocol,
the
registrant
proposed
to
conduct
three
pear
field
trials
and
four
apple
field
trials
each
reflecting
one
application
rate
(
at
a
reduced
rate
of
1.15
lb
ai/
A)
and
an
approximate
PHI
of
70­
170
days
to
coincide
with
petal
fall.
According
to
the
registrant,
the
number
of
planned
field
trials
is
based
on
EPA
Draft
Science
Policy
#
6040
"
Guidance
for
the
Conduct
of
Bridging
Studies
for
Use
in
Acute
Dietary
Probabilistic
Risk
Assessment."
In
its
review
of
submitted
protocol,
HED
recognized
that
the
number
of
planned
pear
and
apple
field
trials
is
in
accordance
with
the
cited
Policy
#
6040;
however,
the
application
scenario
(
only
one
rate)
for
the
planned
studies
would
be
as
per
OPPTS
860.1500
guidelines
and
not
Policy
#
6040.
[
Note:
the
draft
Science
Policy
#
6040
has
since
been
    
17
  
38
incorporated
into
the
final
Science
Policy
paper
#
6063,
"
Guidance
for
Refining
Anticipated
Residue
Estimates
for
Use
in
Acute
Dietary
Probabilistic
Risk
Assessment",
dated
June
15,
2000.]
The
registrant
was
informed
that
as
per
Policy
#
6040,
a
minimum
of
three
different
application
rates
for
each
site
would
be
necessary
in
order
to
compare
or
"
bridge"
results
and
calculate
the
relationship
between
the
original
maximum
application
rate
(
3.68
lb
ai/
A)
that
was
the
basis
for
the
established
apple
and
pear
tolerance
and
the
proposed
lower
rate.

Therefore,
in
order
to
satisfy
reregistration
requirements,
HED's
protocol
review
recommended
two
options:
Option
A
(
bridging
studies
as
per
Policy
#
6040)
or
Option
B
(
crop
field
trials
as
per
860.1500).
For
Option
A,
the
registrant
was
informed
that
they
need
not
perform
pear
bridging
trials
as
long
as
the
apple
bridging
trials
and
resulting
data
are
deemed
adequate.
The
recommendation
to
translate
apple
bridging
data
to
pears
is
based
on
the
identical
use
patterns
of
these
crops
as
per
10/
14/
99
MOA.
For
Option
B,
a
total
of
eight
apple
field
trials
should
be
conducted
at
the
registrant­
proposed
application
rate
in
Regions
1,
5
and
11,
and
a
total
of
four
pear
field
trials
should
be
conducted
at
the
registrant­
proposed
application
rate
in
Regions
10
and
11.
The
860.1500
guidelines
recommend
a
total
of
16
apple
and
8
pear
field
trials.
The
reduced
number
of
trials
recommended
by
HED
takes
into
consideration
the
expectation
of
nondetectable
residues
and
the
reflection
of
regions
representing
the
greatest
formetanate
HCl
use
per
crop.
All
trials
should
reflect
Good
Laboratory
Practice
(
GLP)
and
follow
applicable
recommendations
in
OPPTS
860.1500,
Test
Guidelines
for
Crop
Field
Trials.
A
late
season
application
timing
should
be
included
and
should
coincide
with
the
growing
period
which
would
typically
be
vulnerable
to
late
season
infestations
of
stink
bugs,
lygus
bugs,
and
pear
rust
mites
on
pome
fruit.
If
resulting
data
are
inadequate
to
support
the
new
application
rate
and
PHIs,
then
additional
trials
may
be
required.

Apple
(
MRID
45485002)

In
the
current
study
(
MRID
45485002),
a
total
of
four
apple
field
trials
were
conducted
in
NY
(
1
trial),
MI
(
1
trial),
and
WA
(
2
trials).
In
three
test
sites
(
MI,
NY,
and
WA),
a
representative
92%
SC
formulation
of
formetanate
HCl
was
applied
once
at
petal
fall
as
a
broadcast
spray
at
1.15
lb
ai/
A
(
1x
the
maximum
rate
recommended
rate
by
the
10/
14/
99
MOA).
In
another
WA
trial
location,
the
same
test
formulation
was
applied
twice,
at
petal
fall
and
again
at
crop
maturity
at
1.15
lb
ai/
A
per
application
(
2x);
this
portion
of
the
study
was
conducted
in
order
to
generate
residue
decline
data
but
may
also
be
used
to
determine
residues
resulting
from
a
late
season
application
(
using
the
14
day
PHI
data
to
reflect
the
required
16
day
re­
entry
interval
for
harvesting).
Samples
of
mature
apple
fruits
were
harvested
from
the
1x
treatment
plots
at
107­
134
days
posttreatment.
Fruit
samples
were
also
collected
from
the
2x
plots
at
0,
4,
7,
14,
21,
28,
and
35
days
following
the
last
treatment.
Two
analytical
methods
were
used
to
determine
residues
in/
on
collected
samples.
One
method
(
HPLC/
UV)
measured
only
parent
formetanate
and
the
other
method
(
GC/
ECD)
is
a
common
moiety
method,
slightly
modified
from
PAM
Volume
II,
which
measured
parent
and
several
metabolites
convertible
to
3­
aminophenol.
These
methods
are
adequate
for
data
collection
based
on
acceptable
concurrent
method
recovery
data.
Residues
of
parent
formetanate,
as
determined
by
HPLC/
UV,
were
nondetectable
(<
0.03
ppm)
in/
on
1x­
treated
apples.
As
determined
by
GC/
ECD,
residues
of
formetanate
plus
metabolites
(
measured
as
3­
aminophenol)
ranged
from
nondetectable
(<
0.02
ppm)
to
0.024
ppm
in/
on
1xtreated
samples.

Residues
of
parent
formetanate
in/
on
2x­
treated
apples,
as
determined
by
HPLC/
UV,
were
0.70­
0.79
ppm
at
0­
day
PHI,
0.34­
0.43
ppm
at
14­
day
PHI,
and
0.28­
0.32
ppm
at
35­
day
PHI.
    
18
  
38
The
submitted
residue
data
for
apples
are
not
acceptable
to
support
the
terms
of
the
10/
14/
99
MOA
between
the
Agency
and
the
registrant.
The
number
of
sites
and
geographic
representation
for
conducting
bridging
studies
on
apples
was
adequate
for
Option
A
(
bridging
studies
per
EPA
Science
Policy
#
6040,
draft
version
7/
29/
99);
however,
the
application
scenario
(
only
one
application
rate)
was
not
in
accordance
with
Option
A
requirements.
Application
rates
were
adequate
for
Option
B
(
860.1500
field
trials)
but
the
number
of
field
trials
were
not
adequate.

If
the
registrant
intends
to
conduct
bridging
studies
for
apples
in
accordance
with
Option
A
(
Science
Policy
#
6040),
then
additional
field
trials
that
reflect
the
guidance
as
outlined
above
should
be
conducted
in
Regions
1
and
5/
11;
the
required
study
should
include
the
requirement
for
multiple
application
rates
and
ensuring
that
all
application
rates
used
in
the
bridging
study
result
in
quantifiable
residues.

Alternatively,
if
the
registrant
intends
to
conduct
apple
field
trials
in
accordance
with
Option
B
(
OPPTS
860.1500),
then
at
least
four
additional
field
trials
in
Regions
1,
5,
and
11
must
be
conducted
(
the
trials
should
include
an
early
and
late
season
application
as
allowed
in
the
MOA).

Pear
(
MRID
45485001)

Three
pear
field
trials
were
conducted
in
CA(
1
trial)
and
WA(
2
trials).
In
two
test
sites
(
CA
and
WA),
a
representative
92%
SC
formulation
of
formetanate
HCl
was
applied
once
at
petal
fall
as
a
foliar
airblast
spray
at
1.15
lb
ai/
A
(
1x).
In
another
WA
test
location,
the
same
test
formulation
was
applied
twice,
at
petal
fall
(
3.78
lb
ai/
A)
and
again
at
crop
maturity
(
1.15
lb
ai/
A)
for
a
total
application
of
4.93
lb
ai/
A
(~
4.3x);
this
portion
of
the
study
was
conducted
in
order
to
generate
residue
decline
data.
Samples
of
mature
pear
fruits
were
harvested
from
the
1x
treatment
plots
at
118­
121
days
posttreatment.
Fruit
samples
were
also
collected
from
the
4.3x
plots
at
0,
4,
8,
14,
21,
28,
and
35
days
following
the
last
treatment.
Two
analytical
methods
were
used
to
determine
residues
in/
on
collected
samples.
One
method
(
HPLC/
UV)
measured
only
parent
formetanate
and
the
other
method
(
GC/
ECD)
is
a
common
moiety
method,
slightly
modified
from
PAM
Volume
II,
which
measured
parent
and
several
metabolites.
These
methods
are
adequate
for
data
collection
based
on
acceptable
concurrent
method
recovery
data.

Residues
of
parent
formetanate,
as
determined
by
HPLC/
UV,
were
nondetectable
(<
0.03
ppm)
in/
on
1x­
treated
pears.
As
determined
by
GC/
ECD,
residues
of
formetanate
plus
metabolites
(
measured
as
3­
aminophenol)
were
also
nondetectable
(<
0.02
ppm)
in/
on
1x­
treated
samples.

The
submitted
residue
data
for
pears
are
not
acceptable
to
support
the
terms
of
the
10/
14/
99
MOA
between
the
Agency
and
the
registrant.
The
number
of
sites
and
geographic
representation
for
conducting
bridging
studies
on
pears
was
adequate
for
Option
A
(
bridging
studies
per
Science
Policy
#
6040);
however,
the
application
scenario
(
only
one
application
rate)
was
not
in
accordance
with
Option
A
requirements.
Application
rates
were
adequate
for
Option
B
(
860.1500
field
trials)
but
the
number
of
field
trials
were
not
adequate.

If
the
registrant
intends
to
conduct
bridging
studies
for
pears
in
accordance
with
Option
A,
then
additional
side­
by­
side
field
trials
in
Regions
10
and
11
must
be
conducted.
It
should
be
noted
that
since
the
tolerance­
setting
formetanate
HCl
use
pattern
on
apples
and
pears
is
identical,
as
are
the
new
proposed
use
patterns,
and
since
the
wide
geographic
representation
proposed
for
apples
includes
a
late
season
application
in
the
primary
pear
growing
region,
it
would
be
reasonable
to
translate
the
apple
bridging
data
to
pears.
Therefore,
the
registrant
need
not
perform
pear
bridging
studies
provided
the
apple
bridging
studies
and
resulting
data
are
deemed
adequate.
    
19
  
38
Alternatively,
if
the
registrant
intends
to
conduct
pear
field
trials
in
accordance
with
Option
B
(
860.1500),
then
at
least
two
additional
field
trials
in
Regions
10
and
11
must
be
conducted
(
the
trials
should
include
an
early
and
late
season
application
as
allowed
in
the
MOA).

PEACH
,
NECTARINE
According
to
the
10/
14/
99
MOA,
the
specific
requirements
for
continued
use
of
formetanate
hydrochloride
on
peaches
and
nectarines
include
label
revisions
to
specify
that
the
pesticide
shall
not
be
applied
after
shuck
fall
along
with
a
maximum
application
rate
of
not
more
than
1.15
lb
ai/
A
for
all
food
crops.

In
the
submitted
field
trial
protocol,
the
registrant
proposed
to
conduct
three
peach
field
trials
reflecting
one
application
rate
(
at
a
reduced
rate
of
1.15
lb
ai/
A).
According
to
the
registrant,
the
number
of
planned
field
trials
is
based
on
EPA
Science
Policy
#
6040
"
Guidance
for
the
Conduct
of
Bridging
Studies
for
Use
in
Acute
Dietary
Probabilistic
Risk
Assessment."
In
its
review
of
submitted
protocol,
HED
recognized
that
the
number
of
planned
peach
field
trials
is
in
accordance
with
the
cited
Policy
#
6040;
however,
the
application
scenario
(
only
one
rate)
for
the
planned
study
would
be
as
per
OPPTS
860.1500
guidelines
and
not
Policy
#
6040.
The
registrant
was
informed
that
as
per
Policy
#
6040,
a
minimum
of
three
different
application
rates
for
each
site
would
be
necessary
in
order
to
compare
or
"
bridge"
results
and
calculate
the
relationship
between
the
original
maximum
application
rate
that
was
the
basis
for
establishing
the
peach
tolerance
and
the
proposed
lower
rate.
For
Option
A,
the
registrant
was
informed
that
they
need
not
perform
nectarine
bridging
trials
as
long
as
the
peach
bridging
trials
and
resulting
data
are
deemed
adequate.
The
recommendation
to
translate
peach
bridging
data
to
nectarines
is
based
on
the
identical
use
patterns
of
these
crops
as
per
10/
14/
99
MOA.

For
Option
B,
a
total
of
6
peach
field
trials
should
be
conducted
at
the
registrant­
proposed
application
rate
in
Regions
1,
5
and
11,
and
a
total
of
4
nectarine
field
trials
should
be
conducted
at
the
registrant­
proposed
application
rate
in
Regions
10
and
11.
The
860.1500
guidelines
recommend
a
total
of
12
peach
and
8
nectarine
field
trials.
The
reduced
number
of
trials
recommended
by
HED
takes
into
consideration
the
expectation
of
nondetectable
residues
and
the
reflection
of
regions
representing
the
greatest
formetanate
HCl
use
per
crop.
All
trials
should
reflect
GLP
and
follow
applicable
recommendations
in
OPPTS
860.1500.

Peach
(
MRID
45485003)

Three
peach
field
trials
were
conducted
in
SC(
1
trial),
MI(
1
trial),
and
CA(
1
trial).
In
each
test
site,
a
representative
92%
SC
formulation
of
formetanate
HCl
was
applied
once
at
petal
fall
as
a
broadcast
spray
at
1.15
lb
ai/
A.
Samples
of
mature
peach
fruits
were
harvested
at
57­
124
days
posttreatment.
Two
analytical
methods
were
used
to
determine
residues
in/
on
collected
samples.
One
method
(
HPLC/
UV)
measured
only
parent
formetanate
and
the
other
method
(
GC/
ECD)
is
a
common
moiety
method,
slightly
modified
from
PAM
Volume
II,
which
measured
parent
and
several
metabolites
convertible
to
3­
aminophenol.
These
methods
are
adequate
for
data
collection
based
on
acceptable
concurrent
method
recovery
data.

Residues
of
parent
formetanate,
as
determined
by
HPLC/
UV,
were
nondetectable
(<
0.03
ppm)
in/
on
treated
peaches.
As
determined
by
GC/
ECD,
residues
of
formetanate
plus
metabolites
(
measured
as
3­
aminophenol)
were
also
nondetectable
(<
0.02
ppm)
in/
on
treated
samples.
    
20
  
38
The
submitted
residue
data
for
peaches
are
not
acceptable
to
support
the
terms
of
the
10/
14/
99
MOA
between
the
Agency
and
the
registrant.
The
number
of
sites
and
geographic
representation
for
conducting
bridging
studies
on
peaches
was
adequate
for
Option
A;
however,
the
application
scenario
(
only
one
application
rate)
was
not
in
accordance
with
Option
A
requirements.
Application
rates
were
adequate
for
Option
B
but
the
number
of
field
trials
were
not
adequate.

If
the
registrant
intends
to
conduct
bridging
studies
for
peaches
in
accordance
with
Option
A,
then
additional
side­
by­
side
field
trials
in
Regions
2,
5,
and
10
must
be
conducted.

Alternatively,
if
the
registrant
intends
to
conduct
peach
field
trials
in
accordance
with
Option
B
(
860.1500),
then
results
from
three
additional
field
trials
in
Regions
1
(
or
2),
5,
and
10
must
be
submitted.

Nectarines
(
MRID
45071301)

The
registrant
submitted
the
results
of
a
formetanate
HCL
at­
harvest
study
on
nectarines
(
MRID
45071301).
In
this
study,
nectarine
samples
were
collected
from
California
growers
who
had
treated
the
crops
early
in
the
season
near
the
required
lower
application
rate
of
1.15
lb
ai/
A
(
as
determined
by
grower's
pesticide
application
records).
Sixteen
nectarine
trials
were
conducted
in
CA
(
Region
10).
In
13
trials,
nectarines
were
harvested
87­
116
days
following
a
single
application
of
"
Carzol
90SP"
at
0.9­
1.125
lb
ai/
A.
In
3
trials,
nectarines
were
harvested
77­
87
days
following
the
last
of
two
applications
at
0.99­
1.125
lb
ai/
A.
It
is
unclear
from
the
study
report
if
the
application
rates
listed
for
the
trials
receiving
two
applications
represent
a
single
or
total
application
rate.
Details
pertaining
to
the
field
procedures
used
in
the
study
(
i.
e.,
application
method
and
timing,
equipment,
spray
volumes,
tank
mix
adjuvants)
were
not
provided.

It
is
not
clear
what
end
product
was
used
in
the
trials.
The
only
currently
registered
formetanate
HCL
end
product
is
a
92%
SC
formulation
Carzol
®
SP,
EPA
Reg.
No.
10163­
265.
The
study
reports
that
the
test
substance
and
reference
compound
used
was
Carzol
®
SP,
92%,
EPA
Reg.
No.
45639­
163
[
now
10163­
265].
However,
trial
summary
tables
(
from
grower's
records)
report
that
applications
were
made
using
"
Carzol
90
SP"
applied
as
1.25
lb
product
/
A,
or
1.125
lb
ai/
A.
Calculations
of
active
ingredient
applied
appear
based
on
a
90%
product.
There
are
no
90%
products
registered.
The
EPA
registration
number
for
the
end
product
used
in
the
trials
was
not
reported.

Two
analytical
methods
were
used
to
determine
residues
in/
on
collected
samples.
One
method
(
HPLC/
UV)
measured
only
parent
formetanate
and
the
other
method
(
GC/
ECD)
is
a
common
moiety
method,
slightly
modified
from
PAM
Volume
II,
which
measured
parent
and
several
metabolites.
These
methods
are
adequate
for
data
collection
based
on
acceptable
concurrent
method
recovery
data.

Residues
in/
on
samples
of
nectarines
harvested
87­
116
days
following
a
single
application
of
the
SC
formulation
at
0.9­
1.125
lb
ai/
A
were:
(
i)
nondetectable
(<
0.10
ppm)
as
determined
by
HPLC/
UV,
(
ii)
from
nondetectable
(<
0.02
ppm)
to
0.26
ppm
as
determined
by
GC/
ECD
with
an
RTX­
5
column,
and
(
iii)
from
nondetectable
(<
0.02
ppm)
to
0.29
ppm
as
determined
by
GC/
ECD
with
a
DB­
1701
column.

Residues
in/
on
samples
of
nectarines
harvested
77­
87
days
following
the
last
of
two
applications
of
the
SC
formulation
at
0.99­
1.125
lb
ai/
A
were:
(
i)
nondetectable
(<
0.10
ppm)
as
determined
by
HPLC/
UV;
(
ii)
nondetectable
(<
0.02
ppm)
to
0.49
ppm
as
determined
by
GC/
ECD
with
an
RTX­
5
    
21
  
38
column,
and
(
iii)
nondetectable
(<
0.02
ppm)
to
0.53
ppm
as
determined
by
GC/
ECD
with
a
DB­
1701
column.

The
submitted
nectarine
field
trial
data
are
deemed
inadequate
because
details
pertaining
to
the
field
procedures
used
in
the
study
(
i.
e.,
application
method
and
timing,
equipment,
spray
volumes,
tank­
mix
adjuvants)
and
specific
multiple­
application
rates
were
not
provided.

CITRUS
(
use
limited
to
oranges,
lemons,
limes,
grapefruit,
tangelos,
tangerines)

According
to
the
10/
14/
99
MOA,
the
specific
requirements
for
continued
use
of
formetanate
hydrochloride
on
citrus
fruit
(
limited
to
oranges,
lemons,
limes,
grapefruit,
tangelos,
and
tangerines)
include
label
revisions
to
specify
that
the
pesticide
shall
not
be
applied
after
fruit
reaches
one
inch
in
diameter
along
with
a
maximum
application
rate
of
not
more
than
1.15
lb
ai/
A
for
all
food
crops.
Formetanate
HCl
may
be
applied
to
overcropped
(
both
mature
and
immature
fruit
on
tree
at
time
of
treatment)
grapefruits
and
Valencia
oranges
above
one
inch
in
diameter,
provided
that
a
preharvest
interval
(
PHI)
of
30
days
is
observed.

In
the
submitted
protocol,
the
registrant
proposed
to
conduct
one
orange
(
region
10),
one
lemon
(
region
10),
and
one
grapefruit
(
region
6)
field
trial
reflecting
one
application
rate
(
at
a
reduced
rate
of
1.15
lb
ai/
A)
when
fruit
is
 
1
inch
in
diameter.
For
overcropped
grapefruit
and
Valencia
oranges,
fruit
that
was
mature
at
application
will
be
harvested
at
30
days
PHI
and
fruit
that
was
 
1
inch
in
diameter
will
be
harvested
at
maturity.
According
to
the
registrant,
the
number
of
planned
field
trials
is
based
on
EPA
Science
Policy
#
6040
for
bridging
studies.
In
its
review
of
the
submitted
protocol,
HED
recognized
that
the
number
of
citrus
field
trials
is
in
accordance
with
the
cited
Policy
#
6040;
however,
the
application
scenario
(
only
one
rate)
for
the
planned
study
would
be
as
per
OPPTS
860.1500
guidelines
and
not
Policy
#
6040.
The
registrant
was
informed
that
as
per
Policy
#
6040,
a
minimum
of
three
rates
for
each
site
would
be
necessary
in
order
to
compare
or
"
bridge"
results
and
calculate
the
relationship
between
the
original
maximum
application
rate
(
4.6
lb
ai/
A)
that
was
the
basis
for
establishing
the
citrus
fruit
tolerances
and
the
proposed
lower
rate.

For
Option
B,
a
total
of
three
grapefruit
field
trials
(
region
10)
should
be
conducted
at
the
registrant­
proposed
application
rate.
A
total
of
two
trials
(
region
10)
should
be
conducted
for
lemons
and
six
trails
(
regions
6
and
10)
should
be
conducted
for
oranges.
The
860.1500
guidelines
recommend
a
total
of
6
grapefruit,
5
lemon,
and
12
orange
filed
trials.
The
reduced
number
of
trials
recommended
by
HED
takes
into
consideration
that
formetanate
HCl
use
is
prohibited
in
FL,
the
expectation
of
nondetectable
residues,
and
the
reflection
of
regions
representing
the
greatest
formetanate
HCl
use
per
crop.
All
trials
should
reflect
GLP
and
follow
applicable
recommendations
in
OPPTS
860.1500,
Test
Guidelines
for
Crop
Field
Trials.
If
resulting
data
are
inadequate
to
support
the
new
application
rate
and
PHIs,
then
additional
trials
may
be
required.

In
the
current
study
(
MRID
45798901),
a
total
of
three
field
trials
were
conducted,
one
grapefruit
trial
in
Texas
(
region
6),
one
lemon
trial
in
Arizona
(
region
10),
and
one
orange
trial
in
California
(
region
10).
In
the
trials
a
representative
92%
SC
formulation
of
formetanate
HCl
was
applied
once
by
foliar
airblast
at
1.15
lba.
i/
A.
Applications
were
made
to
grapefruit
at
1"
new
crop
fruit
(
72
BBCH
1),
to
lemons
at
73
BBCH,
and
to
oranges
when
fruit
was
~
40%
of
final
size
(
74
BBCH).
Applications
were
made
when
previous
crop
(
mature)
fruit
was
present.
Samples
(
2
per
trial)
were
collected
at
crop
maturity
(
207­
269
days
after
last
treatment
[
DALA]).
One
method
(
HPLC/
UV)
measured
only
parent
formetanate
and
the
other
method
(
GC/
ECD)
is
a
common
moiety
method,
slightly
modified
from
PAM
Volume
II,
which
measured
parent
and
metabolites
    
22
  
38
convertible
to
3­
aminophenol.
These
methods
are
adequate
for
data
collection
based
on
acceptable
concurrent
method
recovery
data.

Residues
of
parent
formetanate,
as
determined
by
HPLC/
UV,
were
nondetectable
(<
0.03
ppm)
in/
on
1x
treated
citrus
(
immature
fruit
treated
at
1.15
lb
ai/
a
and
harvested
at
maturity,
207­
269
days
PHI).
As
determined
by
GC/
ECD,
residues
of
formetanate
plus
metabolites
were
nondetectable
(<
0.02
ppm)
on
all
1x
treated
samples
except
for
one
orange
sample
at
0.023
ppm.

Samples
of
the
(
old)
mature
crop
(
grapefruit,
lemon,
and
oranges)
present
at
the
time
of
treatment
were
also
collected
at
0,
7,
14,
21,
30,
and
42
days
after
application;
this
portion
of
the
study
was
conducted
in
order
to
generate
residue
decline
data
but
can
also
serve
to
determine
residues
on
(
old)
mature
fruit
at
the
30
day
and
60
day
PHI.

Grapefruit
and
Valencia
oranges
that
were
mature
at
the
time
of
treatment
were
collected
at
a
30­
day
PHI
and
had
average
residues
of
parent
formetanate
at
0.054
ppm
and
0.28
ppm,
respectively,
and
had
residues
of
formetanate
plus
metabolites
at
0.070
ppm
and
0.45
ppm,
respectively.
Mature­
treated
lemons
collected
at
a
30­
day
PHI
had
average
residues
of
parent
formetanate
and
formetanate
plus
metabolites
at
0.98
ppm.

Grapefruit
and
Valencia
oranges
that
were
mature
at
the
time
of
treatment
were
collected
at
a
42­
day
PHI
and
had
average
residues
of
parent
formetanate
at
0.060
ppm
and
0.20
ppm,
respectively,
and
had
residues
of
formetanate
plus
metabolites
at
0.042
ppm
and
0.31
ppm,
respectively.
Mature­
treated
lemons
collected
at
a
42­
day
PHI
had
average
residues
of
parent
formetanate
at
0.46
ppm
and
formetanate
plus
metabolites
at
0.50
ppm.

The
submitted
citrus
field
trial
data
are
deemed
inadequate
to
support
reregistration
requirements
because
the
conducted
study
was
not
in
full
accordance
with
either
Option
A
(
bridging
studies)
or
Option
B
(
crop
field
trials).
If
the
registrant
intends
to
conduct
bridging
studies
for
citrus
in
accordance
with
Option
A,
then
field
trials
should
be
conducted
in
Regions
6
and
10;
the
required
study
should
include
the
requirement
for
multiple
(
side­
by­
side)
application
rates
and
ensuring
that
all
application
rates
used
in
the
bridging
study
result
in
quantifiable
residues.

Alternatively,
if
the
registrant
intends
to
conduct
citrus
field
trials
in
accordance
with
Option
B,
then
5
additional
orange
field
trials
in
Regions
6
and
10
must
be
conducted.
An
additional
lemon
trial
(
region
10)
and
2
additional
grapefruit
trials
(
Regions
6,
10)
are
also
required.

860.1520
Processed
Food
and
Feed
Adequate
apple
and
citrus
processing
studies
are
available
for
tolerance
reassessment
in
processed
commodities.
Residues
of
formetanate
HCl
do
not
concentrate
in
apple
juice
(
0.3x),
orange
juice
(
0.1x),
orange
oil
(
0.1x)
or
dried
citrus
pulp
(
0.8x).
Apple
processing
data
demonstrate
that
a
tolerance
must
be
proposed
for
residues
in
wet
apple
pomace.
Based
on
a
HAFT
residue
value
of
0.38
ppm
from
the
apple
field
trials
(
2
applications,
one
late
season,
for
a
total
of
2.3
lb
ai/
A;
14
day
PHI)
and
an
average
concentration
factor
of
4X
from
four
processing
studies,
a
tolerance
of
1.5
ppm
would
be
appropriate
for
residues
in
apple,
wet
pomace.

1
BBCH
is
a
standardized
system
for
identifying
plant
growth
stages
phenologically.
For
citrus,
BBCH
growth
stage
Code
72
is
defined
as
green
fruit
surrounded
by
sepal
crown.
BBCH
73
is
defined
as
when
some
fruits
slightly
yellow;
beginning
of
physiological
fruit
drop.
BBCH
74
is
when
fruit
is
about
40%
of
final
size
    
23
  
38
860.1850
Confined
Accumulation
in
Rotational
Crops
and
860.1900
Field
Accumulation
in
Rotational
Crops
Since
there
is
a
registered
use
on
alfalfa
grown
for
seed,
a
crop
which
can
be
rotated,
residue
data
for
rotational
crops
is
required.
The
reregistration
data
requirements
for
accumulation
in
rotational
crops
are
tentatively
fulfilled
(
D213962,
C.
Swartz,
10/
10/
95).
The
MOA
requires
that
the
registrant
amend
labels
to
specify
the
following:
Leafy
vegetables
shall
not
be
planted
until
30
days
after
harvest
of
treated
alfalfa..
Root
crops
shall
not
be
planted
until
120
days
after
harvest
of
treated
alfalfa.
Small
grains
and
all
other
crops
shall
not
be
planted
until
12
months
after
harvest
of
treated
alfalfa.
The
existing
EP
label
(
10163­
265)
does
contain
the
required
rotational
crop
restrictions.
(
However,
associated
SLN
AZ030012
instructions
for
use
on
alfalfa
grown
for
seed
do
not
specify
plant
back
intervals.)

860.1550
Proposed
Tolerances
The
tolerances
listed
in
40
CFR
§
180.276
are
expressed
in
terms
of
formetanate
hydrochloride
{
m­
[[(
dimethylamino)
methylene]
­
amino]
phenyl
methylcarbamate
hydrochloride}
and
are
summarized
in
Table
6
below.
Tolerances
were
reassessed
based
on
results
of
either
the
HPLC
method
(
parent
formetanate)
or
the
GC/
ECD
enforcement
method
(
formetanate
plus
metabolites),
whichever
resulted
in
the
higher
residues.

The
established
3
ppm
tolerance
for
residues
of
formetanate
HCl
in
apple
and
pear
may
be
reduced
to
0.50
ppm
based
on
the
new
residue
data
for
apples
where
formetanate
HCl
was
applied
at
the
maximum
rate
and
included
a
late
season
application
(
total
2.3
lb
a.
i/
A
and
14
day
PHI).

The
available
data
for
nectarine
and
peach
indicate
the
established
tolerances
(
4
ppm
and
5
ppm,
respectively)
may
be
reduced
to
0.40
ppm.
Nectarine
data
were
translated
to
peach
data
for
tolerance
reassessment.
Even
though
there
were
no
detectable
residues
(<
0.03)
in
the
peach
trials,
only
two
trials
were
performed.
Since
there
were
a
significant
number
of
detectable
residues
in
nectarines
at
the
new
rate
of
1.15
lb
ai/
A,
it
cannot
automatically
be
assumed
that
there
would
be
no
detects
in
peaches
without
an
adequate
number
of
peach
samples
tested.

Based
on
the
30
day
PHI
residue
data
for
mature­
treated
oranges,
grapefruit
and
lemons
(
1.15
lb
a.
i/
A),
the
tolerances
for
grapefruit
and
orange
may
be
reassessed
at
1.5
ppm.
The
highest
residue
from
the
lemon,
grapefruit,
and
orange
trials
on
mature
fruit
at
a
30
day
PHI
was
used
to
reassess
the
tolerance
for
formetanate
HCl
on
grapefruit
and
orange.

Based
on
the
42
day
PHI
residue
data
for
mature­
treated
oranges,
grapefruit
and
lemons
(
1.15
lb
a.
i/
A),
the
tolerances
for
lemon
(
60
day
PHI
required)
may
be
reassessed
at
0.60
ppm.
The
highest
residue
from
the
lemon,
grapefruit,
and
orange
trials
on
mature
fruit
at
a
42
day
PHI
was
used
to
reassess
the
tolerance
for
formetanate
HCl
on
lemon.

Tolerances
for
residues
of
formetanate
HCl
on
lime,
tangerine
and
tangelo
(
fruit
that
are
not
overcropped)
may
be
reduced
to
0.03
ppm
[
LOQ]
based
on
207
day
PHI
residue
data
for
lemons.

Tolerances
for
residues
of
formetanate
HCl
in
plums,
prune,
fresh
should
be
revoked
as
use
on
    
24
  
38
plums
is
no
longer
permitted.

Apple
processing
data
demonstrate
that
a
tolerance
must
be
proposed
for
residues
in
apple,
wet
pomace.
Based
on
a
HAFT
residue
value
of
0.38
ppm
from
the
apple
field
trials
(
2
applications,
one
of
them
late
season,
for
a
total
of
2.3
lb
ai/
A;
14
day
PHI)
and
an
average
concentration
factor
of
4X
from
four
processing
studies,
a
tolerance
of
1.5
ppm
would
be
appropriate
for
residues
of
formetanate
HCl
in
apple,
wet
pomace.

The
reassessed
tolerances
for
formetanate
HCl
residues
are
based
on
new
field
trials
(
apple,
pear,
peach,
nectarine,
orange,
grapefruit,
lemon)
submitted
in
response
to
the
10/
99
MOA.
While
those
field
trials
generally
reflect
the
new
maximum
rate
and
minimum
PHIs,
the
number
of
field
trials
were
insufficient.
When
the
additional
required
field
trials
are
submitted,
the
tolerance
reassessment
will
be
reevaluated.

No
maximum
residue
limits
(
MRLs)
for
formetanate
HCl
have
been
established
by
Codex
for
any
agricultural
commodity.
Therefore,
no
compatibility
questions
exist
with
respect
to
U.
S.
tolerances.

Table
6.
Tolerance
Reassessment
Summary
for
Formetanate
Hydrochloride
Commodity
Current
Tolerance
(
ppm)
Tolerance
Reassessment
(
ppm)
1
Comment/
[
Correct
Commodity
Definition]

Tolerances
Listed
Under
40
CFR
§
180.276
Apple
3
0.50
Pear
3
0.50
Grapefruit
4
1.5
Lemon
4
0.60
Lime
4
0.03
Oranges
4
1.5
[
orange]

Tangerine
4
0.03
Nectarine
4
0.40
Peach
5
0.40
Plum,
prune,
fresh
2
revoke
no
longer
a
registered
use
Tolerances
To
Be
Proposed
Under
40
CFR
§
180.276
Apple,
wet
pomace
None
1.5
Tangelo
None
0.03
1
Reassessed
tolerances
are
based
on
insufficient
field
trial
data
.
When
additional
acceptable
field
trial
data
are
received,
the
tolerance
reassessment
will
be
reevaluated.
    
25
  
38
Table.
7.
Formetanate
Hydrochloride
Data
Requirements
GLN:
Data
Requirements
Current
Tolerances,
ppm
[
40
CFR]
Must
Additional
Data
Be
Submitted?
References
i
860.1200:
Directions
for
Use
N/
A
=
Not
Applicable
No
See
Tables
3
and
4.

860.1300:
Plant
Metabolism
N/
A
Yes
ii
00077703,
00077711,
40280501,
42684605
iii,
455956012
860.1300:
Livestock
Metabolism
N/
A
No
00164328,
00164329,
42664414­
42664417
iv,
43329001
v,
43329002
5
860.1340:
Residue
Analytical
Methods
­
Plant
commodities
N/
A
No
00029161,
00035917,
40411802
­
Livestock
commodities
N/
A
No
40557601
860.1360:
Multiresidue
Methods
N/
A
No
42664406
vi,
42983201
vii
860.1380:
Storage
Stability
Data
N/
A
No
viii
00077702,
40411803,
42664407
4,
42664408
4,
42723601
4,
43329003
5,
43384401­
43384405
ix,
43610401­
43610403
x
860.1500:
Crop
Field
Trials
Citrus
Fruits
(
Citrus
spp.,
Fortunella
spp.)
Group
­
Grapefruit
4
[
180.276]
Yes17
00077665,
00077702,
41708501
xi,
41708502
11,
41708505
11,4579890117
    
26
  
38
GLN:
Data
Requirements
Current
Tolerances,
ppm
[
40
CFR]
Must
Additional
Data
Be
Submitted?
References
i
­
Lemon
4
[
180.276]
Yes17
00077702,
4170850211,
41708505
11,4579890117
­
Lime
4
[
180.276]
Yes17
00077702
xii,
4579890117
­
Orange
4
[
180.276]
Yes17
00073455,
00077665,
00077702,
41708501
11,
41708503
11,41708504
11,
4579890117
­
Tangelo
None
Yes17
00077768,
4579890117
­
Tangerine
4
[
180.276]
Yes17
00077768,
4579890117
Pome
Fruits
Group
­
Apple
3
[
180.276]
Yes18
00077702,
00077710,
45485002
18
­
Pear
3
[
180.276]
Yes18
00077710,
45485001
18
Stone
Fruits
Group
­
Nectarine
4
[
180.276]
Yes19
00077762,
40411803,
42664410
4,
4507130119
­
Peach
5
[
180.276]
Yes18
00077762,
40411803,
45485003
18
­
Plum
2
[
180.276]
No
00077762
Non­
Grass
Animal
Feeds
­
Alfalfa
seed,
forage,
and
hay
None
established
No
xiii
40534301
860.1520:
Processed
Food/
Feed
­
Apple
None
established
No
00077721
    
27
  
38
GLN:
Data
Requirements
Current
Tolerances,
ppm
[
40
CFR]
Must
Additional
Data
Be
Submitted?
References
i
­
Citrus
None
Established
No
00073455,
00077665,
00077702
­
Plum
None
Established
No
00077762
860.1480:
Meat,
Milk,
Poultry,
Eggs
­
Milk
and
the
Fat,
Meat,
and
Meat
Byproducts
of
Cattle,
Goats,
Hogs,
Horses,
and
Sheep
None
established
No
41299601­
41299603
xiv
­
Eggs
and
the
Fat,
Meat,
and
Meat
Byproducts
of
Poultry
None
established
No
xv
860.1400:
Water,
Fish,
and
Irrigated
Crops
None
established
N/
A
860.1460:
Food
Handling
None
established
N/
A
860.1850:
Confined
Rotational
Crops
N/
A
No21
43170401
xvi,
43583101xvii
860.1900:
Field
Rotational
Crops
None
established
No
20
1
Bolded
references
were
reviewed
in
the
Residue
Chemistry
Chapter
of
the
Formetanate
HCl
Second
Round
Review
(
SRR)
dated
5/
10/
89.
Unbolded
references
were
reviewed
in
the
Residue
Chemistry
Chapter
of
the
Formetanate
Reregistration
Standard
dated
9/
30/
82.
All
other
references
were
reviewed
as
noted.

ii.
DP
Barcode
D281044,
2/
10/
03,
D.
Drew.
The
registrant
must
provide
supporting
chromatographic
evidence
for
their
statement
that
a
Day­
0
leaf
extract
was
found
to
be
stable
for
13
months,
and
justification
for
use
of
a
Day­
0
leaf
extract
to
support
the
storage
of
an
extract
of
peach
fruit
for
up
to
9
months
prior
to
analysis.

iii.
CBRS
No.
11518,
DP
Barcode
D189020,
1/
7/
97,
C.
Swartz.

iv.
CBRS
No.
11729,
DP
Barcode
D190256,
5/
18/
94,
C.
Swartz.

v.
CBRS
No.
14240,
DP
Barcode
D206806,
2/
10/
97,
C.
Swartz.

vi.
Forwarded
to
FDA
for
review
(
memo
dated
5/
21/
93
from
L.
Edwards
to
H.
Hundley).
    
28
  
38
vii.
Forwarded
to
FDA
for
review
(
CBRS
No.
12806,
DP
Barcode
D196721,
11/
22/
93,
L.
Edwards).

viii.
Residues
of
the
metabolite
3­
formamidophenyl­
N­
methylcarbamate
declined
after
storage
intervals
of
9­
33
months.
Additional
data
pertaining
to
this
metabolite
will
not
be
required
at
this
time,
as
that
metabolite
has
been
determined
to
be
not
of
significant
toxicological
concern.

ix.
CBRS
No.
14534,
DP
Barcode
D208231,
2/
11/
97,
C.
Swartz.

x.
CBRS
No.
15469,
DP
Barcode
D214581,
9/
19/
95,
C.
Swartz.

xi.
CB
No.
7522,
3/
11/
91,
F.
Toghrol.

xii.
CBRS
No.
12887,
DP
Barcode
D197102,
2/
4/
97,
C.
Swartz.

xiii.
The
use
on
alfalfa
grown
for
seed
in
CA,
ID,
NV,
OR,
WA
and
AZ
is
considered
to
be
a
nonfood
use,
since
these
states
have
established
programs
designed
to
prevent
diversion
of
alfalfa
forage,
hay,
seed,
and
seed
screenings
(
from
treated
alfalfa
grown
for
seed)
to
livestock
feed.
No
data
and
no
tolerances
for
residues
in
alfalfa
commodities
are
required.

xiv.
CB
Nos.
6127,
6128,
and
6129,
4/
18/
90,
R.
Perfetti.

xv.
Currently
there
are
no
registered
uses
of
formetanate
HCl
on
any
poultry
feed
items
and
there
are
no
direct
livestock
treatments
of
formetanate
HCl
to
poultry;
therefore,
a
poultry
feeding
study
and
tolerances
for
residues
in
poultry
commodities
are
not
required.

xvi.
CBRS
No.
13459,
DP
Barcode
D201138,
5/
2/
94,
C.
Swartz.

17.
DP
Barcode
286406,
1/
15/
03,
D.
Drew.
Five
additional
orange
field
trials
in
Regions
6
and
10
must
be
conducted.
An
additional
lemon
trial
(
region
10)
and
2
additional
grapefruit
trials
(
Regions
6,
10)
are
also
required.

18.
DP
Barcode
D278011,
1/
8/
03,
D.
Drew.
Apples:
at
least
four
additional
field
trials
in
Regions
1,
5,
and
11
must
be
conducted
(
the
trials
should
include
an
early
and
late
season
application
as
allowed
in
the
MOA;
Pears:
at
least
two
additional
field
trials
in
Regions
10
and
11
must
be
conducted
(
the
trials
should
include
an
early
and
late
season
application
as
allowed
in
the
MOA);
Peaches:
three
additional
field
trials
in
Regions
1
(
or
2),
5,
and
10
must
be
submitted.

19.
DP
Barcode
D265072,
2/
10/
03,
D.
Drew.
Details
pertaining
to
the
field
procedures
used
in
the
study
(
i.
e.,
application
method
and
timing,
equipment,
spray
volumes,
tank
mix
adjuvants)
and
multiple
application
rates
must
be
provided.

20.
CBRS
No.
15403,
DP
Barcode
D213962,
10/
5/
95,
C.
Swartz.

21.
Since
there
is
a
registered
use
on
alfalfa
grown
for
seed,
a
crop
which
can
be
rotated,
residue
data
for
rotational
crops
are
required.
The
reregistration
data
requirements
for
accumulation
in
rotational
crops
are
tentatively
fulfilled.
The
10/
99
MOA
requires
that
the
registrant
amend
labels
to
specify
the
following:
Leafy
vegetables
shall
not
be
planted
until
30
days
after
harvest
of
treated
alfalfa.
Root
crops
shall
not
be
planted
until
120
days
after
harvest
of
treated
alfalfa.
Small
grains
and
all
other
crops
shall
not
be
planted
until
12
months
after
harvest
of
treated
alfalfa.
    
29
  
38
AGENCY
MEMORANDA
RELEVANT
TO
REREGISTRATION
CB
Nos.:
6127,
6128,
and
6129
Subject:
Nor­
Am
Chemical
Co.
Response
to
the
Formetanate
Hydrochloride
Reregistration
Standard:
Ruminant
Feeding
Studies.
From:
R.
Perfetti
To:
R.
Engler
and
L.
Rossi
Dated:
4/
18/
90
MRID(
s):
41299601­
41299603
CB
No.:
7522
Subject:
Formetanate
Hydrochloride
(
Carzol
®
SP)
in
or
on
Citrus.
Amendment
to
the
Registration
of
Carzol
SP
(
EPA
Reg.
No.
45639­
74)
to
Change
the
Application
Intervals
from
30
Days
to
14
Days
in
CA
and
AZ.
From:
F.
Toghrol
To:
D.
Edward/
C.
Andreasen
Dated:
3/
11/
91
MRID(
s):
41708501­
41708505
CB
No.:
None
DP
Barcode:
None
Subject:
Formetanate.
HCl
through
FDA
Multi­
Residue
Protocols
A
through
E.
List
A,
Case
#
0091.
From:
L.
Edwards
To:
H.
Hundley
Dated:
5/
21/
93
MRID(
s):
42664406
CBRS
No.:
12806
DP
Barcode:
D196721
Subject:
Reregistration
of
Formetanate.
HCl.
Multi­
Residue
Testing
Data
of
Formetanate.
List
A
Case
No.
0091.
From:
L.
Edwards
To:
L.
Schnaubelt/
S.
Jennings
Dated:
11/
22/
93
MRID(
s):
42983201
    
30
  
38
CBRS
No.:
13459
DP
Barcode:
D201138
Subject:
Formetanate
Hydrochloride.
List
A
Reregistration
Case
No.
0091/
Chemical
ID
No.
097301.
Confined
Rotational
Crop
Study.
From:
C.
Swartz
To:
L.
Schnaubelt/
S.
Jennings
Dated:
5/
2/
94
MRID(
s):
43170401
CBRS
No.:
11729
DP
Barcode:
D190256
Subject:
Formetanate
Hydrochloride.
List
A
Reregistration
Case
No.
0091/
Chemical
ID
No.
097301.
Nature
of
the
Residue
in
Ruminants
and
Poultry;
Residue
Analytical
Methods;
Storage
Stability;
Magnitude
of
the
Residue
in
Nectarines.
From:
C.
Swartz
To:
L.
Schnaubelt
Dated:
5/
18/
94
MRID(
s):
42664406,
42664407,
42664408,
42664410,
42664414­
42664417,
and
42723601
CBRS
No.:
17066
DP
Barcode:
D224582
Subject:
Formetanate
HCl
(
List
A,
Case
No.
0091).
Anticipated
Residues
for
Chronic
Non­
Cancer
Dietary
Exposure
Assessment.
Gowan
Company.
Chemical
No:
097301
From:
D.
Hrdy
To:
W.
Hazel
Dated:
8/
26/
96
MRID(
s):
None
CBTS
No.:
13795
DP
Barcode:
D203797
Subject:
PP#
4F4357.
Formetanate
Hydrochloride.
List
A
Reregistration
Case
No.
0091/
Chemical
ID
No.
097301.
Petition
for
Tolerances
in/
on
Alfalfa
Forage
and
Hay.
From:
C.
Swartz
To:
D.
Edwards
Dated:
9/
19/
95
MRID(
s):
None
CBRS
No.:
15469
DP
Barcode:
D214581
Subject:
Formetanate
Hydrochloride.
List
A
Reregistration
Case
No.
0091/
Chemical
ID
No.
097301.
Guideline
171­
4(
e):
Storage
Stability
Data
in
Apples,
Citrus
and
Stone
Fruit.
From:
C.
Swartz
To:
L.
Schnaubelt/
S.
Jennings
Dated:
9/
19/
95
MRID(
s):
43610401,
43610402,
and
43610403
CBRS
No.:
15403
DP
Barcode:
D213962
Subject:
Formetanate
Hydrochloride.
List
A
Reregistration
Case
No.
0091/
Chemical
ID
No.
097301.
Submission
to
Upgrade
the
Confined
Rotational
Crop
Study.
From:
C.
Swartz
To:
L.
Schnaubelt/
S.
Jennings
    
31
  
38
Dated:
10/
5/
95
MRID(
s):
43583101
CBRS
No.:
11518
DP
Barcode:
D189020
Subject:
Formetanate
Hydrochloride.
List
A
Reregistration
Case
No.
0091/
Chemical
ID
No.
097301.
Citrus
Metabolism
Study.
From:
C.
Swartz
To:
W.
Hazel
Dated:
1/
7/
97
MRID(
s):
42684605
CBRS
No.:
12887
DP
Barcode:
D197102
Subject:
Formetanate
Hydrochloride.
List
A
Reregistration
Case
No.
0091/
Chemical
ID
No.
097301.
Nor­
Am's
Submission
to
Support
Use
of
Formetanate
Hydrochloride
on
Limes.
From:
C.
Swartz
To:
C.
Scheltema
Dated:
2/
4/
97
MRID(
s):
None
CBRS
No.:
14240
DP
Barcode:
D206806
Subject:
Formetanate
Hydrochloride.
List
A
Reregistration
Case
No.
0091/
Chemical
ID
No.
097301.
Registrant
Submission
to
Upgrade
Animal
Metabolism
and
Storage
Stability
Studies.
From:
C.
Swartz
To:
W.
Hazel
Dated:
2/
10/
97
MRID(
s):
43329001,
43329002,
and
43329003
CBRS
No.:
14534
DP
Barcode:
D208231
Subject:
Formetanate
Hydrochloride.
List
A
Reregistration
Case
No.
0091/
Chemical
ID
No.
097301.
Registrant
Submission
of
Storage
Intervals
Incurred
During
Citrus
Residues
Studies.
From:
C.
Swartz
To:
C.
Scheltema
Dated:
2/
11/
97
MRID(
s):
43384401
through
43384405
CBRS
No.:
None
DP
Barcode:
None
Subject:
Formetanate
Hydrochloride.
List
A
Reregistration
Case
No.
0091/
Chemical
ID
No.
097301.
Issues
to
be
presented
at
the
2/
19/
97
meeting
of
the
HED
Metabolism
Committee.
From:
C.
Swartz
To:
HED
Metabolism
Committee
Dated:
2/
19/
97
MRID(
s):
None
CBRS
No.:
13544
DP
Barcode:
D201901
Subject:
Formetanate
Hydrochloride.
List
A
Reregistration
Case
No.
0091/
Chemical
ID
No.
097301.
Registrant
Submission
to
Supplement
Animal
Metabolism
Studies.
    
32
  
38
From:
C.
Swartz
To:
C.
Scheltema
Dated:
2/
27/
97
MRID(
s):
43090000,
43090001,
43179901,
and
43144701
CBRS
No.:
None
DP
Barcode:
None
Subject:
Formetanate
Hydrochloride.
List
A
Reregistration
Case
No.
0091/
Chemical
ID
No.
097301.
Outcome
of
the
2/
19/
97
meeting
of
the
HED
Metabolism
Committee.
From:
C.
Swartz
To:
HED
Metabolism
Committee
Dated:
4/
15/
97
MRID(
s):
None
CBRS
No.:
17752
DP
Barcode:
D233099
Subject:
Formetanate
hydrochloride.
List
A
Reregistration
Case
No.
0091/
Chemical
ID
No.
097301.
HED
RED:
Product
and
Residue
Chemistry
Chapters.
From:
C.
Swartz
To:
R.
Perfetti
Dated:
4/
18/
97
MRID(
s):
None
DP
Barcode:
D234261
Subject:
Formetanate
Hydrochloride.
List
A
Reregistration
Case
No.
0091/
Chemical
ID
No.
097301.
Response
to
Review
of
Citrus
Metabolism
Study.
From:
D.
Drew
To:
M.
Goodis
Dated:
12/
2/
98
MRID(
s):
None
DP
Barcode:
D250747
Subject:
Formetanate
Hydrochloride.
List
A
Reregistration
Case
No.
0091/
Chemical
ID
No.
097301.
Magnitude
of
the
Residue
on
Oranges,
Analytical
Method
for
Determining
Residues
on
Oranges.
From:
D.
Drew
To:
M.
Goodis
Dated:
12/
10/
98
MRID(
s):
44674002,
44674003
DP
Barcode:
D263912
Subject:
Formetanate
HCL:
Review
of
Residue
Chemistry
Proposals
Received
from
Registrant
as
Required
in
the
10/
14/
99
Memorandum
of
Agreement.
Chemical
097301.
From:
D.
Drew
To:
D.
Fuller
Dated:
3/
15/
2000
MRID(
s):
None
DP
Barcode:
D281044
Subject:
Formetanate
Hydrochloride.
List
A
Reregistration
Case
No.

0091/
Chemical
ID
No.
097301
Metabolism
of
[
U­
14C­
phenyl]­
Formetanate
Hydrochloride
in
Peaches.
From:
D.
Drew
To:
D.
Fuller
    
33
  
38
Dated:
2/
10/
03
MRID(
s):
None
DP
Barcode:
D278011
Subject:
Formetanate
HCL:
Crop
Field
Trials­
Pears,
Apples,
Peaches.
Case
no.
0091/
PC
Code
097301.
From:
D.
Drew
To:
D.
Fuller
Dated:
1/
8/
2003
MRID(
s):
45485001,
45485002,
45485003
DP
Barcode:
D286406
Subject:
Formetanate
HCL:
Crop
Field
Trials­
Citrus.
Case
no.
0091/
PC
Code
097301.
From:
D.
Drew
To:
D.
Fuller
Dated:
1/
15/
2003
MRID(
s):
45798901
DP
Barcode:
D265072
Subject:
Formetanate
HCL:
Review
of
Field
Trial
residue
Data
on
Nectarines
Submitted
by
Aventis
CropScience.
Case
no.
0091/
PC
Code
097301.
From:
D.
Drew
To:
D.
Fuller
Dated:
2/
10/
2003
MRID(
s):
45485001,
45485002,
45485001
DP
Barcode:
D250747
Subject:
Formetanate
Hydrochloride.
List
A
Reregistration
Case
No.
0091/
Chemical
ID
No.
097301.
Magnitude
of
the
Residue
on
Oranges,
Analytical
Method
for
Determining
Residues
on
Oranges.
From:
D.
Drew
To:
M.
Goodis
Dated:
12/
10/
98
MRID(
s):
44674002,
44674003
MASTER
RECORD
IDENTIFICATION
NUMBERS
00029161
Nor­
Am
Agricultural
Products,
Incorporated
(
1969)
332/
30:
Colorimetric
Determination
of
Formetanate
HCl.
(
Nor­
Am
EP­
332)
in
Plant
Material:
(
Schering
36
056/
5
Revised).
Method
dated
May
22,
1969.
(
Unpublished
study
received
May
22,
1980
under
OE2363;
submitted
by
Interregional
Research
Project
No.
4,
New
Brunswick,
N.
J.;
CDL:
099438­
B)

00035917
Jenny,
N.
A.
(
1969)
Gas
Chromatographic
Residue
Determination
of
Formetanate
HC1
(
Nor­
Am
Carzol)
in
Plant
Material:
Report
332/
41.
Method
dated
Nov
7,
1969.
(
Unpublished
study
received
Feb
1,
1973
under
3F1351;
submitted
by
Nor­
Am
Agricultural
Products,
Inc.,
Naperville,
Ill.;
CDL:
096476­
F)

00073455
Morton
Chemical
Company
(
1968)
[
Residues
of
Formetanate
on
Oranges,
Grapefruit
and
Lemons].
(
Compilation;
unpublished
study
received
Nov
29,
1968
under
9G0746;
CDL:
091290­
E)

00077665
Nor­
Am
Agricultural
Products,
Incorporated
(
1975)
Residues
of
Formetanate
Hydrochloride
in
Citrus
Treated
with
Carzol
SP
by
Air.
Includes
method
332/
30
dated
May
22,
1969.
(
Compilation;
unpublished
study
received
Mar
12,
1975
under
2139­
99;
CDL:
110595­
A)

00077702
Nor­
Am
Agricultural
Products,
Incorporated
(
1970)
[
Residue
Data
on
Carzol
SP
in
    
34
  
38
Citrus
Fruits].
(
Compilation;
unpublished
study
received
Apr
12,
1970
under
0F0961;
CDL:
091643­
D)

00077703
Knowles,
C.
O.;
Sen
Gupta,
A.
K.
(
1970)
Metabolism
of
Formetanate
Acaricide
by
Orange
Seedlings.
(
Unpublished
study
received
Apr
12,
1970
under
0F0961;
prepared
by
Univ.
of
Missouri,
Dept.
of
Entomology,
submitted
by
Nor­
Am
Agricultural
Products,
Inc.,
Naperville,
Ill.;
CDL:
091643­
E)

00077710
Nor­
Am
Agricultural
Products,
Incorporated
(
1970)
Formetanate
Hydrochloride
Residues
in
Apples
and
Pears:
The
Results
of
Tests
on
the
Amount
of
Residue
Remaining,
Including
a
Description
of
the
Analytical
Method
Used.
(
Compilation;
unpublished
study
received
on
unknown
date
under
0F0989;
CDL:
091703­
B)

00077711
Schering
AG
(
1969)
The
Fate
of
Formetanate
Hydrochloride
Residues
on
Apples:
2nd
Report
1969
on
Formetanate
Residues.
(
Unpublished
study
received
Apr
12,
1970
under
0F0961;
submitted
by
Nor­
Am
Agricultural
Products,
Inc.,
Naperville,
Ill.;
CDL:
091643­
L)

00077721
Nor­
Am
Agricultural
Products,
Incorporated
(
1973)
Residues
of
Formetanate
Hydrochloride
in
Apple
Products.
(
Compilation;
unpublished
study,
including
letter
dated
Oct
8,
1973
from
M.
Lambert
to
Edward
Gross,
received
Apr
25,
1973
under
3H5029;
CDL:
221762­
F)

00077762
Nor­
Am
Agricultural
Products,
Incorporated
(
1971)
Formetanate
Hydrochloride:
Results
of
Tests
on
the
Amount
of
Residue
Remaining:
Peaches,
Plums,
Prunes,
Nectarines,
Grapes.
(
Compilation;
unpublished
study
received
Aug
14,
1972
under
2F1238;
CDL:
091095­
A)

00077768
Nor­
Am
Agricultural
Products,
Incorporated
(
1971)
[
Formetanate
Hydrochloride
Residues
in
Grapes
and
Tangerines].
(
Compilation;
unpublished
study
received
Apr
13,
1971
under
1F1141;
CDL:
090928­
A)

00164328
Campbell,
J.;
Needham,
D.
(
1986)
Metabolism
and
Residues
of
Formetanate
Hydrochloride
in
Laying
Hens:
Proj.
ID.
No.
METAB/
86/
36.
Unpublished
study
prepared
by
Schering
Agrochemicals
Ltd.
24
p.

00164329
Campbell,
J.;
Needham,
D.
(
1986)
Excretion
and
Tissue
Residues
of
Formetanate
Hydrochloride
in
a
Lactating
Goat:
Proj.
ID.
No.
METAB/
86/
28.
Unpublished
study
prepared
by
Schering
Agrochemicals
Ltd.
24
p.

40280501
Celorio,
J.
(
1986)
M15­
Formetanate
HCl:
Fate
of
Formetanate
Hydrochloride
in
Alfalfa
(
Medicago
sativa
L.):
Laboratory
Project
ID:
UPSR
30/
86­
PA
36
056.81/
12.
Unpublished
study
prepared
by
Schering
AG.
45
p.

40411802
R155/
Formetanate
HCl:
GLC
Method
of
Analysis
for
Major
Formetanate
Derived
Residues
in
Nectarines
(
10
970
1/
87):
Laboratory
Project
ID
UPSR
32/
87
PA
10
970.5/
11.
Unpublished
study
prepared
by
Schering
AG.
28
p.

40411803
Scheuermann,
H.
(
1987)
R156
Formetanate
HCl:
Residues
of
Formetanate
X
HCl
and
Major
Metabolites
in
Stone
Fruits
Following
Foliar
Application
of
CARZOL
(
92
SP)
in
the
USA
1985
and
1986
(
10
970
11/
87):
Laboratory
Project
ID
UPSR
36/
87
PA
10
970.6/
11.
Unpublished
study
prepared
by
Schering
AG.
43
p.

40534301
Scheuermann,
H.
(
1988)
R157
Formetanate:
Residue
Decline
of
Formetanate
x
HCl
and
Major
Metabolites
in
Alfalfa
Following
Foliar
Application
of
Carzol
(
90SP)
in
the
USA
1985
(
10970
III/
87):
Laboratory
Project
ID
UPSR
50/
87.
Unpublished
study
prepared
by
Schering
AG,
Germany.
52
p.

40557601
Manley,
J.;
Snowdon,
P.
(
1988)
R154
Formetanate:
Analytical
Method
for
the
    
35
  
38
Determination
of
Residues
of
Formetanate
and
Major
Metabolites
Hydrolysing
to
3­
Aminophenol
in
Animal
Tissues,
Milk
and
Eggs
by
Gas
Chromatography:
Laboratory
Project
ID
RESID/
87/
82.
Unpublished
study
prepared
by
Schering
Agrochemicals
Limited,
England.
38
p.

41299601
Roberts,
N.;
Cameron,
D.;
Emerson,
E.
(
1988)
R163A
Formetanate
Hydrochloride:
Residues
in
Milk
&
Tissues
of
Dairy
Cows­­
Animal
Phase:
Lab
Project
Number
RESID/
88/
44;
FSB
275/
861445;
101/
05/
001.
Unpublished
study
prepared
by
Huntingdon
Research
Centre.
23
p.

41299602
Snowdon,
P.;
Manley,
J.
(
1989)
R163
Formetanate­
derived
Residues
Containing
the
3­
Aminophenol
Moiety
in
the
Tissues
and
Milk
of
Cattle
following
a
28­
Day
Feeding
Study
in
the
UK,
1986:
Lab
Project
Number
RESID/
88/
44;
101/
05/
001.
Unpublished
study
prepared
by
Schering
Agrochemicals
Ltd.
43
p.
41299603
Manley,
J.;
Snowdon,
P.
(
1989)
C49
Formetanate:
Analytical
Method
for
the
Determination
of
Dietary
Concentrations
of
Formetanate
Hydrochloride
in
Maize
Oil
by
High
Performance
Liquid
Chromatography:
Lab
Project
Number
RESID/
88/
46;
101/
01/
002.
Unpublished
study
prepared
by
Schering
Agrochemicals
Ltd.
20
p.

41708501
J.
Moede.
(
1988).
R165
FORMETANATE:
Residues
of
formetanate
x
+
HCl
and
major
metabolites
in
citrus
following
application
of
CARZOL
92
SP
in
the
USA
1988.
Laboratory
Study
No.
UPSR
89/
88.
Unpublished
study
conducted
by
Schering
AG,
Berlin,
Germany
and
submitted
by
Nor­
Am
(
Wilmington,
DE).
133
p.

41708502
A.
Wrede­
Rucker.
(
1990).
R176
FORMETANATE
HCL:
Residues
of
formetanate
x
HCl
and
major
metabolites
in
citrus
following
application
of
CARZOL
92
SP
in
the
USA
1989.
Laboratory
Study
No.
UPSR
6/
90.
Unpublished
study
conducted
by
Schering
AG,
Berlin,
Germany
and
submitted
by
Nor­
Am
(
Wilmington,
DE).
41
p.

41708503
A.
Wrede­
Rucker.
(
1990).
R177
FORMETANATE
HCL:
Residues
of
formetanate
x
HCl
and
major
metabolites
in
oranges
following
application
of
CARZOL
SP
92
in
the
USA
1989.
Laboratory
Study
No.
UPSR
7/
90.
Unpublished
study
conducted
by
Schering
AG,
Berlin,
Germany
and
submitted
by
Nor­
Am
(
Wilmington,
DE).
37
p.

41708504
A.
Wrede­
Rucker.
(
1990).
R178
FORMETANATE
HCL:
Residues
of
formetanate
x
HCl
and
major
metabolites
in
oranges
following
application
of
CARZOL
92
SP
in
the
USA
1989.
Laboratory
Study
No.
UPSR
8/
90.
Unpublished
study
conducted
by
Schering
Agrochemicals
Limited,
Essex,
England
and
submitted
by
Nor­
Am
(
Wilmington,
DE).
38
p.

41708505
A.
Wrede­
Rucker.
(
1990).
R179
FORMETANATE
HCL:
Residues
of
formetanate
x
HCl
and
major
metabolites
in
citrus
following
application
of
CARZOL
92
SP
in
the
USA
1989.
Laboratory
Study
No.
UPSR
11/
90.
Unpublished
study
conducted
by
Schering
Agrochemicals
Limited,
Essex,
England
and
submitted
by
Nor­
Am
(
Wilmington,
DE).
48
p.

42664406
Bowman,
M.
(
1992)
Testing
of
Formetanate
HCl
(
R187)
through
U.
S.
FDA
Multiresidue
Methods:
U.
S.
A.,
1992:
Lab
Project
Number:
MCB­
NOR­
AM/
MR­
5:
Y­
92R­
03.
Unpublished
study
prepared
by
M.
C.
Bowman
&
Associates.
76
p.

42664407
Wrede­
Rucker,
A.
(
1992)
Stability
of
Formetanate
X
HCl
and
its
Metabolite
ZK
10
714
during
Deep
Freeze
Storage
in
Peaches:
Interim
Report:
(
R191
Formetanate
HCl):
Lab
Project
Number:
U/
R
43/
92:
020906:
PF­
R
92
029.
Unpublished
study
prepared
by
Schering
AG.
27
p.

42664408
Wrede­
Rucker,
A.
(
1992)
Stability
of
Formetanate
HCl
and
its
Metabolite
ZK
10
714
during
Deep
Freeze
Storage
in
Apples:
Interim
Report:
(
R191
Formetanate
HCl):
Lab
Project
Number:
U/
R/
45/
92:
020907.
Unpublished
study
prepared
by
Schering
AG.
27
p.

42664410
Brady,
S.
(
1992)
At­
harvest
Formetanate­
derived
Residues
in
or
on
Nectarines
following
Treatment
with
Carzol
SP
(
Aerial
and
Ground)
at
Maximum
Use
Rates:
USA,
1991:
Lab
    
36
  
38
Project
Number:
Y­
91R­
01.
Unpublished
study
prepared
by
NOR­
AM
Chemical
Co.
42
p.

42664414
Reynolds,
C.
(
1993)
The
Nature
of
the
Residues
of
Formetanate
HCl
in
the
Edible
Tissues
and
Milk
of
a
Cow
following
Oral
Administration
for
7
days
at
a
Dose
Equivalent
of
30
ppm
in
the
Diet:
Lab
Project
Number:
TOX
92/
197­
76:
020910:
T0X
91044.
Unpublished
study
prepared
by
Schering
Agrochemical
Ltd.
170
p.

42664415
O'Boyle,
F.
(
1993)
The
Nature
of
Residues
of
Formetanate
HCl
in
the
Edible
Tissues
of
the
Laying
Hen
following
Oral
Administration
for
14
days
at
a
Dose
Equivalent
to
10
ppm
in
the
Diet:
Lab
Project
Number:
TOX
91045A:
020910:
TOX/
92/
197­
77.
Unpublished
study
prepared
by
Schering
Agrochemical
Ltd.
109
p.

42664416
Little,
E.
(
1992)
Absorption,
Distribution
and
Excretion
following
Multiple
Oral
Administration
to
the
Dairy
Cow:
(
carbon
14)­
Formetanate
HCl:
Lab
Project
Number:
7294­
194/
68:
TOX
91044:
TOX/
92/
197­
73.
Unpublished
study
prepared
by
Hazleton
UK
and
Schering
Agrochemicals
Ltd.
59
p.

42664417
Reynolds,
C.
(
1992)
The
Excretion
and
Distribution
of
Formetanate
HCl
and
its
Metabolites
in
the
Laying
Hen
following
Daily
Oral
Administration
at
a
Dose
Rate
Equivalent
to
10
ppm
in
the
Diet:
Lab
Project
Number:
TOX
92/
197­
74:
020911:
TOX
91045.
Unpublished
study
prepared
by
Schering
Agrochemical
Ltd.
27
p.

42684605
Downey,
S.
(
1993)
Metabolism
of
(
carbon
14)­
Formetanate
in
Lemons:
Lab
Project
Number:
504Y.
Unpublished
study
prepared
by
Nor­
Am
Chemical
Co.
52
p.

42723601
Scheuermann,
H.
(
1990)
Stability
of
Formetanate
X
HCl
in
Alfalfa
during
Deep
Freeze
Storage:
Lab
Project
Number:
UPSR
56/
90:
4010.
Unpublished
study
prepared
by
Schering
AG.
20
p.

42983201
Williams,
L.
(
1993)
Testing
of
Formetanate.
HCl
Through
Protocol
A
of
US
FDA
Multiresidue
Methods:
Lab
Project
Number:
Y­
92R­
08.
Unpublished
study
prepared
by
NORAM
Chemical
Co.
26
p.

43170401
Smith,
S.
(
1994)
Uptake
of
(
carbon
14)­
Formetanate
Residues
in
Soil
by
Rotational
Crops
under
Confined
Conditions:
Lab
Project
Number:
503Y.
Unpublished
study
prepared
by
Nor­
Am
Chemical
Co.
167
p.

43329001
Reynolds,
C.
(
1994)
The
Nature
of
Residues
of
Formetanate
HCl
in
the
Edible
Tissues
and
Milk
of
a
Cow
Following
Oral
Administration
for
7
Days
at
a
Dose
Equivalent
of
30
ppm
in
the
Diet:
M19­
Addendum
1:
Lab
Project
Number:
TOX/
92/
197/
76.
Unpublished
study
prepared
by
Schering
Agrochemicals
Ltd.
99
p.

43329002
O'Boyle,
F.
(
1994)
The
Nature
of
Residues
of
Formetanate
HCl
in
the
Edible
Tissues
of
the
Laying
Hen
Following
Oral
Administration
for
14
Days
at
a
Dose
Equivalent
to
10
ppm
in
the
Diet:
M20­
Addendum
1:
Lab
Project
Number:
TOX/
92/
197/
77.
Unpublished
study
prepared
by
Schering
Agrochemicals
Ltd.
69
p.

43329003
Czochor,
L.
(
1994)
Response
to
EPA
Review
of
Formetanate
Hydrochloride
Storage
Stability
Data
Base.
Unpublished
study
prepared
by
AgrEvo
USA
Co.
17
p.

43384401
Wrede,
A.
(
1994)
Formetanate
HCl
R165­
Addendum
to
Report:
Residues
of
Formetanate
x
HCl
and
Major
Metabolites
in
Citrus
Following
Application
of
CARZOL
92
SP
in
the
USA
1988:
Lab
Project
Number:
UPSR
89/
88:
PF­
R88056.
Unpublished
study
prepared
by
Schering
AG
and
Hoechst
Schering
AgrEvo
GmbH.
13
p.

43384402
Wrede,
A.
(
1994)
Formetanate
HCl
R176­
Addendum
to
Report:
Residues
of
Formetanate
x
HCl
and
Major
Metabolites
in
Citrus
Following
Application
of
CARZOL
92
SP
in
    
37
  
38
the
USA
1989:
Lab
Project
Number:
UPSR/
6/
90:
PF/
R89010.
Unpublished
study
prepared
by
Schering
AG
and
Hoechst
Schering
AgrEvo
GmbH.
13
p.

43384403
Wrede,
A.
(
1994)
Formetanate
HCl
R177­
Addendum
to
Report:
Residues
of
Formetanate
x
HCl
and
Major
Metabolites
in
Oranges
Following
Application
of
CARZOL
92
SP
in
the
USA
1989:
Lab
Project
Number:
UPSR
7/
90:
PF­
R90003.
Unpublished
study
prepared
by
Schering
AG
and
Hoechst
Schering
AgrEvo
GmbH.
12
p.

43384404
Wrede,
A.
(
1994)
Formetanate
HCl
R178­
Addendum
to
Report:
Residues
of
Formetanate
x
HCl
and
Major
Metabolites
in
Oranges
Following
Application
of
CARZOL
92
SP
in
the
USA
1989:
Lab
Project
Number:
UPSR
8/
90:
PF­
R90006.
Unpublished
study
prepared
by
Schering
AG
and
Hoechst
Schering
AgrEvo
GmbH.
12
43384405
Wrede,
A.
(
1994)
Formetanate
HCl
R179­
Addendum
to
Report:
Project
Number:
UPSR
11/
90:
PF­
R90007.
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{
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{
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cc::
D.
Drew,
List
File
RDI:
RRB3
Chemists
(
3/
24/
03);
C.
Eiden
(
3/
24/
03);
ChemSAC
(
3/
26/
03)