Document ID: EPA-HQ-OPP-2004-0048-0006
Agency: epa
Document Type: Supporting & Related Material
Title: 
Posted Date: 2004-06-18T04:00Z

UNITED
STATES
ENVIRONMENTAL
PROTECTION
AGENCY
WASHINGTON,
D.
C.
20460
OFFICE
OF
PREVENTION,
PESTICIDES
AND
TOXIC
SUBSTANCES
MEMORANDUM
Date:
4/
30/
04
Subject:
Amitraz.
TRED
­
Report
on
FQPA
Tolerance
Reassessment
Progress
and
Interim
Risk
Management
Decisions.
Product
Chemistry
Considerations.
Case
No.
0234.

DP
Barcode:
D300301
PC
Code:
106201
From:
José
J.
Morales,
Chemist
Reregistration
Branch
3
Health
Effects
Division
(
7509C)

Through:
Danette
Drew,
Branch
Senior
Scientist
Reregistration
Branch
3
Health
Effects
Division
(
7509C)

To:
John
Pates,
Chemical
Review
Manager
Reregistration
Branch
1
Special
Review
and
Reregistration
Division
(
7508C)
Amitraz
Product
Chemistry
Considerations
­
TRED
Barcode:
D300301
2
Executive
Summary
Amitraz
[
N'­(
2,4­
dimethylphenyl)­
N­[[(
2,4­
dimethylphenyl)
imino]
methyl]­
Nmethylmethanimidamide
is
an
insecticide/
acaricide
with
registered
food/
feed
uses
in
the
U.
S.
on
cotton,
pears,
beef
and
dairy
cattle,
and
hogs.
Amitraz
is
currently
registered
for
use
on
cotton
to
control
various
insects
(
bollworm
larvae
and
eggs,
beet
armyworm,
whitefly,
aphids,
and
spider
mites)
as
well
as
on
pears
for
the
control
of
pear
psylla
and
grape
mealybug.
Amitraz
can
be
applied
by
airblast
and
concentrate
spray
(
pears)
with
up
to
3.0
lb
a.
i./
acre
applied
during
dormancy
and
throughout
the
growing
season
excluding
prebloom
applications.
It
can
also
be
applied
via
ground
boom
or
aircraft
(
cotton)
with
up
to
1.0
lb
a.
i./
acre
during
the
growing
season
with
a
maximum
of
eight
applications
per
year.
Current
formulations
include:
wettable
powder,
emulsifiable
concentrate,
and
soluble
concentrate/
liquid.
In
addition,
an
import
tolerance
has
been
established
to
support
amitraz
use
on
hops
to
be
imported
into
the
U.
S.
Amitraz
products
with
food/
feed
uses
are
registered
in
the
U.
S.
to
Bayer
CropScience
(
BCS)
LP
and
Intervet,
Inc.
under
the
trade
names
Ovasyn
®
,
Mitac
®
,
and
Taktic
®
.
Currently,
the
1.5
lb/
gal
soluble
concentrate
(
SC),
50%
wettable
powder
(
WP),
and
12.5%
emulsifiable
concentrate
(
EC)
formulations
are
registered
for
use
on
food/
feed
sites.
The
SC
formulation
is
registered
for
use
on
cotton,
and
the
WP
formulation
is
registered
for
use
on
pears.
The
EC
formulation
is
registered
for
use
on
cattle
and
swine
as
dermal
treatments.

Amitraz
is
also
used
for
tick
control
on
dogs
as
well
as
mite
and
lice
management
on
beef
cattle,
dairy
cattle
and
swine.
In
the
case
of
tick
and
flea
collars
(
Preventic
®
and
Preventic
®
Plus),
application
should
be
made
every
three
months
in
dogs
more
than
12
weeks
of
age.
Additionally,
amitraz
can
be
applied
via
dip
or
low
pressure
hand
spray
for
cattle
and
swine
with
up
to
0.2
lb
a.
i./
50
gallons
of
water.
For
the
use
of
Taktic
E.
C.
on
beef
cattle,
dairy
cattle
and
swine,
the
following
application
methods
are
suggestedl:
1)
cattle
applied
via
spraying
or
by
a
spray
dip
machine,
2)
swine
applied
via
spraying,
and
3)
piglets/
weaners
applied
by
dipping.
However,
Taktic
E.
C.
is
not
to
be
applied
within
three
days
of
slaughter
for
swine,
which
are
not
to
be
treated
more
than
four
times
per
year.
All
of
the
established
tolerances
for
meats,
meat
byproducts
and
milk
will
be
maintained
to
support
the
animal
health
uses.

In
a
recent
letter
to
the
Agency,
BCS
has
decided
to
voluntarily
withdraw
the
registrations
of
Ovaysn
Insecticide/
Miticide
(
EPA
Reg.
No.
264­
625)
and
Mitac
W
Insecticide
(
EPA
Reg.
No.
264­
636).
The
registrant
has
also
requested
to
maintain
the
registration
of
technical
amitraz,
to
revoke
established
tolerances
for
apples,
beeswax,
honey,
and
pears
as
well
as
maintain
import
tolerances
for
hops
and
cottonseed
(
Amitraz
Use
Closure
Memo,
10/
22/
03).

Amitraz
is
a
FIFRA
List
A
chemical.
The
Amitraz
Reregistration
Standard,
dated
10/
84,
required
additional
product
chemistry
data
for
the
Nor­
Am
"
stabilized"
amitraz
technical
(
93%
T;
EPA
Reg.
No.
45639­
51).
In
response
to
the
Amitraz
Reregistration
Standard,
Nor­
Am
submitted
new
product
chemistry
data
for
a
97%
technical
product
with
the
same
EPA
Reg.
No.
The
Amitraz
Reregistration
Standard
Update,
dated
7/
6/
90,
summarized
the
available
product
chemistry
database
for
the
reregistration
of
amitraz.
Although
the
Update
identified
the
product
as
a
93%
product,
Nor­
Am
subsequently
confirmed
that
the
nominal
concentration
was
97%.
As
of
the
Product
Chemistry
Chapter
of
the
Amitraz
Reregistration
Eligibility
Decision
(
RED),
dated
Amitraz
Product
Chemistry
Considerations
­
TRED
Barcode:
D300301
3
N
N
N
C
H
3
CH
3
C
H
3
CH
3
CH
3
9/
17/
93
(
the
Amitraz
RED
was
signed
03/
95),
the
registrant
had
resolved
all
outstanding
product
chemistry
issues.
However,
OPPTS
830
Series
Test
Guidelines
now
require
data
concerning
the
UV/
visible
absorption
of
the
PAI
(
830.7050).

All
pertinent
product
chemistry
data
requirements
are
satisfied
for
the
only
registered
manufacturing
use
product,
the
Bayer
CropSciences
97%
T,
except
that
data
are
required
concerning
the
UV/
visible
absorption
of
the
PAI
(
OPPTS
830.7050).
Provided
that
the
registrant
submits
the
data
required
in
the
attached
data
summary
table
for
the
amitraz
technical
product,
and
either
certifies
that
the
suppliers
of
beginning
materials
and
the
manufacturing
process
have
not
changed
since
the
last
comprehensive
product
chemistry
review
or
submits
a
complete
updated
product
chemistry
data
package,
the
Agency
has
no
objections
to
the
reregistration
of
amitraz
with
respect
to
product
chemistry
data
requirements.

Product
Chemistry
Deficiencies
Data
are
required
concerning
the
UV/
visible
absorption
of
the
PAI
(
OPPTS
830.7050)
for
the
Bayer
97%
T
(
EPA
Reg.
No.
264­
614).

Background
Identification
of
Active
Ingredient
The
PC
code
and
nomenclature
of
amitraz
are
listed
below
in
Table
1.
The
physicochemical
properties
of
amitraz
are
listed
in
Table
2.

Table
1.
Amitraz
Nomenclature
Chemical
structure
Common
name
Amitraz
Molecular
Formula
C19H23N3
Molecular
Weight
293.42
IUPAC
name
N­
methylbis(
2,4­
xylyliminomethyl)
amine
CAS
name
N'­(
2,4­
dimethylphenyl)­
N­[[(
2,4­
dimethylphenyl)
imino]
methyl]­
Nmethylmethanimidamide
CAS
#
33089­
61­
1
PC
Code
106201
Current
Food/
Feed
Site
Registration
Cotton,
pear,
beef
and
dairy
cattle,
hog
Amitraz
Product
Chemistry
Considerations
­
TRED
Barcode:
D300301
4
Table
2.
Physicochemical
Properties
of
Amitraz.

Parameter
Value
Reference
Melting
point/
range
86­
87

C
Amitraz
RED,
03/
95
pH
of
1%
aqueous
suspension
N/
A
(
low
solubility;
decomposes
in
water)
Amitraz
RED,
03/
95
Density
or
specific
gravity
1.128
g/
mL
at
20

C
Amitraz
RED,
03/
95
Water
solubility
<
1
ppm
at
20­
25

C
Amitraz
RED,
03/
95
Solvent
solubility
At
20­
25

C
xylene
66.6
g/
100
mL
acetone
50.0
g/
100
mL
methanol
2.38
g/
100
mL
Amitraz
RED,
03/
95
Vapor
pressure
3.4
x
10­
4
Pa
at
25

C
Amitraz
RED,
03/
95
Octanol/
water
partition
coefficient
(
Kow)
3.0
x
105
at
25

C
(
pH
5.8)
CBRS
No.
3975,
7/
21/
88,
H.
Fonouni.

Manufacturing­
use
Products
A
search
of
the
OPPIN
product
listings
conducted
6/
9/
03
identified
a
single
manufacturing­
use
product
(
MP)
registered
under
PC
Code
106201:
the
Bayer
CropScience
LP
97%
technical
product
(
T;
EPA
Reg.
No.
264­
614).
The
Bayer
97%
T
was
transferred
2/
22/
00
from
AgrEvo
USA
Company
(
formerly
Nor­
Am
Chemical
Company;
EPA
Reg.
No.
45639­
51).
The
Bayer
97%
T
(
EPA
Reg.
No.
264­
614)
is
the
only
MP
subject
to
a
reregistration
eligibility
decision.

830.1550­
7950
Product
Chemistry
Data
Requirements
The
current
status
of
the
product
chemistry
data
requirements
for
the
Bayer
97%
T
is
presented
in
the
attached
data
summary
table.
Refer
to
this
table
for
a
listing
of
the
outstanding
product
chemistry
data
requirements.
Amitraz
Product
Chemistry
Considerations
­
TRED
Barcode:
D300301
5
Case
No.
0234
Chemical
No.
106201
Case
Name:
Amitraz
Registrant:
Bayer
CropScience
LP
Product(
s):
97%
T
(
EPA
Reg.
No.
264­
614)

PRODUCT
CHEMISTRY
DATA
SUMMARY
Guideline
Number
Requirement
Are
Data
Requirements
Fulfilled?
1
MRID
Number
2
830.1550
Product
identity
and
composition
Y
00030051,
40650703
3,
CSF
6/
24/
96
4
830.1600
Description
of
materials
used
to
produce
the
product
Y
40650701
3
830.1620
Description
of
production
process
Y
40650701
3
830.1670
Discussion
of
formation
of
impurities
Y
40650701
3
830.1700
Preliminary
analysis
Y
40650702
3
830.1750
Certified
limits
Y
40650703
3,
CSF
6/
24/
96
4
830.1800
Enforcement
analytical
method
Y
40650704
3,
40650705
3,
40650706
3
830.6302
Color
Y
40650707
3
830.6303
Physical
state
Y
40650707
3
830.6304
Odor
Y
40650707
3
830.6313
Stability
to
normal
and
elevated
temperatures,
metals,
and
metal
ions
Y
41068403
5
830.6314
Oxidation/
reduction:
chemical
incompatibility
Y
42496001
6
830.6315
Flammability
Y
42496001
6
830.6316
Explodability
Y
42496001
6
830.6317
Storage
stability
Y
41068403
5,
43041001
7
830.6319
Miscibility
N/
A
8
830.6320
Corrosion
characteristics
Y
42496001
6
830.7000
pH
N/
A
9
830.7050
UV/
Visible
absorption
N
10
830.7100
Viscosity
N/
A
8
830.7200
Melting
point/
melting
range
Y
40650707
3
830.7220
Boiling
point/
boiling
range
N/
A
8
830.7300
Density/
relative
density/
bulk
density
Y
40650707
3
830.7370
Dissociation
constants
in
water
Y
41068404
5
830.7550
Partition
coefficient
(
n­
octanol/
water),
shake
flask
method
Y
40650707
3
830.7840
Water
solubility:
column
elution
method;
shake
flask
method
Y
40650707
3,
41068401
5,
41068402
5
830.7950
Vapor
pressure
Y
40650707
3
1
Y
=
Yes;
N
=
No;
N/
A
=
Not
Applicable.
The
Bayer
97%
T
was
transferred
from
AgrEvo
(
formerly
Nor­
Am
Chemical
Company;
EPA
Reg.
No.
45639­
51).
The
data
summarized
above
reflect
new
product
chemistry
data
submitted
by
Nor­
Am;
Nor­
Am
has
confirmed
that
the
97%
T
was
the
test
substance
used
to
generate
the
current
product
chemistry
database
(
D193083,
9/
3/
93,
F.
Toghrol).
Bayer
must
confirm
that
the
manufacturing
process
and
location
have
not
changed
since
the
product
transfer;
otherwise,
additional
product
chemistry
data
may
be
required.
Amitraz
Product
Chemistry
Considerations
­
TRED
Barcode:
D300301
6
2
Bolded
references
were
reviewed
in
the
Amitraz
Reregistration
Standard,
dated
10/
84;
and
all
other
references
were
reviewed
as
noted.

3
CBRS
No.
3975,
7/
21/
88,
H.
Fonouni.

4
RD
memorandum,
D241309,
2/
18/
98,
P.
Hong.

5
D185748,
D187485,
D188495,
and
D192950,
7/
27/
93,
F.
Griffith.

6
D183795,
12/
22/
92
and
D193083,
9/
3/
93,
F.
Toghrol.

7
D198187,
5/
12/
94,
C.
Swartz.

8
Data
are
not
required
because
the
TGAI/
MP
is
a
solid
at
room
temperature.

9
Data
are
not
required
because
the
TGAI
is
practically
insoluble
in
water.

10
The
OPPTS
Series
830,
Product
Properties
Test
Guidelines
require
data
pertaining
to
UV/
visible
absorption
for
the
PAI.
Amitraz
Product
Chemistry
Considerations
­
TRED
Barcode:
D300301
7
BIBLIOGRAPHY
Study
Citations
40650701
Johnson,
M.
(
1987)
Amitraz
Manufacturing
Process
and
Discussion
of
Formation
of
Impurities;
Description
of
Beginning
Materials:
Project
ID:
AD
49/
87;
AD
51/
87.
Unpublished
study
prepared
by
Schering
Agrochemicals,
Ltd.
49
p.

40650702
Lal,
S.;
Brahm,
M.
(
1987)
Preliminary
Analysis
of
Technical
Amitraz
Determination
of
N­
Nitrosamines
in
Technical
Amitraz:
Project
ID:
AD
62/
87;
A.
C.
57/
86.
Unpublished
study
prepared
by
Schering
Agrochemicals,
Ltd.,
and
Schering
AG.
41
p.

40650703
Johnson,
M.
(
1987)
Amitraz
Chemical
Product
Composition:
Project
ID:
AD
56/
87.
Unpublished
study
prepared
by
Schering
Agrochemicals,
Ltd.
6
p.

40650704
Leyte,
A.
(
1987)
The
Determination
of
Amitraz
in
Technical
Material
and
Formulations
by
Gas
Chromatography
(
GC):
The
Validation
of
the
Analytical
Method
AM
1800/
1/
6
for
the
Determination
of
Amitraz
in
its
Technical
Material
and
Gettable
Powder
Formulation:
Project
ID;
AM
1800/
6/
1
and
AD/
65/
87.
Unpublished
study
prepared
by
Schering
Agrochemicals,
Ltd.
19
p.

40650705
Lal,
S.
(
1987)
The
Determination
of
Bis
27919,
BIS
27271,
BIS
28037,
and
BIS
24868
Impurities
in
Amitraz
Technical
by
Gas
Chromatography:
An
Assessment
of
the
Accuracy
in
Technical
Amitraz
by
Gas
Chromatography:
Project
ID:
AM
No.
1800/
5/
1;
AD
68/
87.
Unpublished
study
prepared
by
Schering
Agrochemicals,
Ltd.
33
p.

40650706
Lal,
S.
(
1987)
The
Determination
of
(...)
in
Technical
Amitraz
by
Gas
Chromatography
(
GC):
An
Assessment
of
the
Accuracy
and
Precision
of
the
Analytical
Method
(
AM
1800/
6/
1)
for
the
Determination
of
(...)
in
Technical
Amitraz
by
Gas
Chromatography:
Project
ID:
AM
1800/
6/
1;
AD
69/
87.
Unpublished
study
prepared
by
Schering
Agrochemicals,
Ltd.
13
p.

40650707
Johnson,
M.;
Leyte,
A.;
Bright,
A.;
et
al.
(
1987)
Amitraz:
Physical
and
Chemical
Characteristics:
Project
No.
AD
52/
87
CHEM/
87/
78.
Unpublished
study
prepared
by
Schering
Agrochemicals,
Ltd.
88
p.

41068401
Scott,
G.;
Bright,
A.
(
1989)
C180
Amitraz:
Solubility
in
Organic
Solvents
at
25
C:
Proj.
ID
CHEM2/
89/
008.
Unpublished
study
prepared
by
Schering
Agrochemicals,
Ltd.
22
p.

41068402
Bright,
A.;
Scott,
G.
(
1989)
C180
Addendum
1
Amitraz:
Solubility
in
Organic
Solvents:
Proj.
ID
CHEM/
88/
26.
Unpublished
study
prepared
by
Schering
Agrochemicals,
Ltd.
7
p.

41068403
Johnson,
M.
(
1989)
C181
An
Assessment
of
the
Sensitivity
of
Technical
Amitraz
to
Metals
and
Metal
Ions:
Proj.
ID
AD
4/
89.
Unpublished
study
prepared
by
Schering
Agrochemicals,
Ltd.
6
p.
Amitraz
Product
Chemistry
Considerations
­
TRED
Barcode:
D300301
8
41068404
Bright,
A.;
Lows,
P.
(
1989)
C182
Amitraz:
Determination
of
the
pKa:
Proj.
ID
CHEM2/
89/
009.
Unpublished
study
prepared
by
Schering
Agrochemicals,
Ltd.
29
p.

42496001
Baker,
G.;
Finch,
C.
(
1992)
Amitraz
Technical:
Product
Chemistry:
Lab
Project
Number:
REP/
87/
9(
C152):
F1008­
92.01/
4R(
C293).
Unpublished
study
prepared
by
NOR­
AM
Chemical
Co.
21
p.

43041001
Finch,
C.
(
1993)
The
Determination
of
Storage
Stability
of
Amitraz
Technical:
Lab
Project
Number:
F1008­
92.01/
3.
Unpublished
study
prepared
by
NOR­
AM
Chemical
Co.
22
p.
Amitraz
Product
Chemistry
Considerations
­
TRED
Barcode:
D300301
9
Agency
Memoranda
Citations
CBRS
No(
s).:
3975
Subject:
Amitraz
Registration
Standard
Response
From:
H.
Fonouni
To:
D.
Edwards
Dated:
7/
21/
88
MRID(
s):
40650701­
40650707
DP
Barcode(
s):
D183795
Subject:
Amitraz
Reregistration:
A
List
A
Chemical
(
Chemical
No.
106201;
Case
No.
0234).
NOR­
AM:
Response
to
the
Amitraz
Product
Chemistry
Update
(
dated
8/
6/
90
[
sic.])
Regarding
the
Oxidizing/
Reducing
Action,
Flammability,
Explodability,
and
Corrosion
Characteristics.
From:
F.
Toghrol
To:
L.
Rossi
Dated:
12/
22/
92
MRID(
s):
42496001
DP
Barcode(
s):
D185748,
D187485,
D188495,
and
D192950
Subject:
PP#
2F4110
­
Amitraz
(
Tactic
®
)
on
Hogs.
Review
of
the
December
16,
1992;
January
19,
February
12,
and
July
12,
1993,
Amendments.
From:
F.
Griffith
To:
D.
Edwards
Dated:
7/
27/
93
MRID(
s):
42496001,
41068401­
04,
40650707,
42632001,
and
42667001
DP
Barcode(
s):
D193083
Subject:
Nor­
Am:
Response
(
letter
dated
6/
14/
93)
to
the
Amitraz
Product
Chemistry
Data
Requirements
(
dated
12/
22/
93)
Regarding
the
Test
Material
Used
in
Oxidizing/
Reducing
Action,
Flammability,
Explodability,
and
Corrosion
Characteristics
(
Guideline
Nos.
63­
14,
63­
15,
63­
16,
and
63­
20)
Studies.
From:
F.
Toghrol
To:
L.
Rossi
Dated:
9/
3/
93
MRID(
s):
None.
Amitraz
Product
Chemistry
Considerations
­
TRED
Barcode:
D300301
10
DP
Barcode(
s):
D198187
Subject:
Amitraz.
List
A
Reregistration
Case
No.
0234/
Chemical
ID
No.
106201.
Guideline
No.
63­
17:
Storage
Stability.
From:
C.
Swartz
To:
L.
Propped
Dated:
5/
12/
94
MRID(
s):
43041001
DP
Barcode(
s):
RD
Memorandum,
D241309
Subject:
Product
Chemistry
Review
of
Manufacturing­
Use
Product;
Reg.
No.:
45639­
51;
Product
Name:
Amitraz
Insecticide
Technical;
Company
Name:
AgrEvo
USA
Co.
From:
P.
Hong
To:
C.
Moran
Dated:
2/
18/
98
MRID(
s):
None
[
summary
of
previously
reviewed
MRIDs]