
Page
1
of
5
UNITED
STATES
ENVIRONMENTAL
PROTECTION
AGENCY
WASHINGTON,
D.
C.
20460
OFFICE
OF
PREVENTION,
PESTICIDES
AND
TOXIC
SUBSTANCES
November
22,
2005
MEMORANDUM
SUBJECT:
Triadimenol:
Summary
of
Product
Chemistry
Data
for
Tolerance
Reassessment
(
TRED)
Document.

DP
Barcode:
D315152
PC
Code:
127201
Chemical
Class:
Azole
FROM:
P.
Yvonne
Barnes,
Chemist
Reregistration
Branch
2
Health
Effects
Division
[
7509C]

THROUGH:
Alan
Nielsen,
Branch
Senior
Scientist
Reregistration
Branch
2
Health
Effects
Division
[
7509C]

TO:
Richard
Griffin,
Risk
Assessor
Reregistration
Branch
2
Health
Effects
Division
[
7509C]

The
summary
analytical
chemistry
and
residue
data
document
was
originally
prepared
under
contract
by
Dynamac
Corporation,
The
Dynamac
Building
2275
Research
Boulevard
Rockville,
MD
20850­
3268.
Page
2
of
5
TRIADIMENOL
TOLERANCE
REASSESMENT
DESCISION
(
TRED)

PRODUCT
CHEMISTRY
CONSIDERATIONS
PC
Code
127201
DESCRIPTION
OF
CHEMICAL
Triadimenol
is
a
triazole
systemic
fungicide
registered
as
a
as
a
seed
treatment
for
corn,
cotton,
small
grains,
and
sorghum
in
the
United
States.
Chemical
Name:
[
beta­(
4­
chlorophenoxy)­
alpha­(
1,1­
dimethylethyl)­
1H­
1,2,4­
triazole­
1­
ethanol].
IUPAC
name:
(
1RS,
2RS;
1RS,
2SR)­
1­(
4­
klorfenoxi)­
3,
3­
dimetyl­
1­(
1H­
1,
2,
4­
­
triazol­
1­
yl)
butan­
2­
ol.

Chemical
Structure:
Triadimenol
Empirical
Formula:
C14H18ClN3O2
Molecular
Weight:
295.77
grams
Chemistry
Abstract
Service
[
CAS]
Registry
Number:
55219­
65­
3
PC
Code:
127201
IDENTIFICATION
OF
TECHNICAL
GRADE
ACTIVE
INGREDIENT
Triadimenol
is
a
colorless
crystalline
solid
mixture
of
two
diastereoisomers
with
a
melting
point
of
109
º
C
 
115
º
C,
specific
gravity
of
1.22,
and
vapor
pressure
of
<
1
mPa
at
20
º
C.
Triadimenol
is
slightly
soluble
in
water
(
0.012
g/
100g
at
20
º
C),
toluene
(
1g
­
5
g/
100
g),
methylene
chloride
(
10g
­
20g
/
100
g),
and
cyclohexanone
(
40g
­
60
g/
100
g),
and
is
insoluble
in
aliphatic
hydrocarbons.
MANUFACTURING­
USE
PRODUCTS
Page
3
of
5
A
search
of
the
Reference
Files
System
(
REFS)
conducted
03/
06/
2000
identified
a
single
triadimenol
manufacturing­
use
product
(
MP)
registered
under
PC
Code
127201:
the
Bayer
Corporation
(
formerly
Mobay
Chemical
Corporation)
98.4
percent
technical
(
Technical,
T;
EPA
Registration
Number:
3125­
347).
Only
the
Bayer
Corporation's
98.4
percent
technical
grade
active
ingredients
[
T/
TGAI]
are
subject
to
a
reregistration
eligibility
decision.

REGULATORY
BACKGROUND
Because
triadimenol
was
registered
after
FIFRA
88,
no
comprehensive
reregistration
reviews
have
been
completed.
Product
chemistry
data
for
triadimenol
were
originally
reviewed
in
conjunction
with
PP#
3F2854
(
RCB
Memorandum,
08/
01/
1983,
A.
Smith).
The
status
of
the
data
requirements
for
the
product
chemistry
of
triadimenol
technical
grade
active
ingredient
[
TGAI]
is
presented
in
the
data
summary
table
below.
Refer
to
this
table
for
a
listing
of
the
outstanding
product
chemistry
data
requirements.

CONCLUSIONS
HED
has
no
objections
to
this
reregistration
if
and
only
if:

(
1)
The
registrant
must
provide
the
required
data
to
fulfill
the
data
gap(
s)
listed
in
Table
1.
(
2)
The
registrant
certifies
that
the
suppliers
beginning
materials
and
the
manufacturing
process
for
the
T/
TGAI
have
not
changed
since
the
last
comprehensive
product
chemistry
review.
(
3)
Alternatively,
to
satisfy
OPPTS
830
Series
Guidelines,
the
registrant
must
submit
a
new
complete
updated
Product
Chemistry
Data
Package.

DATA
REQUIREMENTS
The
registrant
must
submit
the
data
required
in
the
following
guidelines:

1.
OPPTS
Guideline
830.6313,
Normal
and
elevated
temperatures,
and
upon
exposure
to
metals
and
metal
ions
2.
OPPTS
Guideline
830.7000,
pH.
3.
OPPTS
Guideline
830.7050,
UV/
VIS
Absorption.
4.
OPPTS
Guidelines
830.7550,
830.7560,
or
830.7570,
N­
octanol/
water
partition
data.
5.
OPPTS
Guideline
830.7840
or
830.7860,
Water
Solubility.
Page
4
of
5
AGENCY
MEMORANDA
CITED
IN
THIS
DOCUMENT
CBRS
Number(
s):
RD
Memorandum
DP
Barcode(
s):
D237331
Subject:
Product
Chemistry
Review.
Registration/
File
Symbol
Number:
3125­
347,
Baytan
Technical,
Bayer
Corporation.
From:
A.
Smith
To:
J.
Whitehurst
Dated:
08/
22/
1997
MRID(
s):
None
CBRS
Number(
s):
RD
Memorandum
DP
Barcode(
s):
D250514
Subject:
Product
Chemistry
Review
of
a
Technical
Grade
Active
Ingredient
[
TGAI].
Registration/
File
Symbol
Number:
3125­
347,
Baytan
Technical,
90%,
CAS
#
55219­
65­
3,
Bayer
Corporation.
From:
S.
Malak
To:
C.
Giles­
Parker/
M.
Rodriguez
Dated:
01/
07/
1999
MRID(
s):
44656901
CBRS
Number(
s):
RD
Memorandum
DP
Barcode(
s):
D252880
Subject:
Product
Chemistry
Review
of
a
Technical
Grade
[
TGAI].
Registration/
File
Symbol
Number:
3125­
347,
Baytan
Technical,
98.4%,
CAS
#
55219­
65­
3,
Bayer
Corp.
From:
S.
Malak
To:
C.
Giles­
Parker/
M.
Rodriguez
Dated:
02/
09/
1999
MRID(
s):
None
PRODUCT
CHEMISTRY
CITATIONS
Bibliographic
citations
include
only
Master
Record
Identification
[
MRIDs]
containing
data,
which
fulfill
data
requirements.

References
(
cited):

00125399
Mobay
Chemical
Corporation
(
1983)
Product
Chemistry
of
Baytan.
(
Compilation;
unpublished
study
received
March
11,
1983
under
3125­
346;
CDL:
071461­
A)

44656901
Fontaine,
L.
(
1998)
Product
Chemistry
of
Baytan
Technical:
Lab
Project
Number:
82248:
ANR­
03898:
ANR­
03998.
Unpublished
study
prepared
by
Bayer
Corporation.
145
p.
Page
5
of
5
Table
1
:
Product
Chemistry
Data
Summary
of
Triadimenol
OPPTS
Guideline
Number
Chemical
Name:
Triadimenol
[
Technical]

CAS
Number:
55219­
65­
3
PC
Code:
127201
Formula:
C14H18ClN3O2
Master
Record
Identification
[
MRID]
or
Reference
Data
Requirements
Completed
Results
or
*
Data
Gap
830.1550
Product
identity
and
composition
00125399
Yes
CSF
1997,
1999
830.1600
Description
of
materials
used
to
produce
the
product
00125399,
44656901
Yes
830.1620
Description
of
production
process
00125399,
44656901
Yes
830.1650
Description
of
formulation
process
00125399,
44656901
Yes
830.1670
Discussion
of
formation
of
impurities
00125399,
44656901
Yes
830.1700
Preliminary
analysis
00125399,
44656901
Yes
830.1750
Certified
limits
00125399
Yes
CSF
1997,
1999
830.1800
Enforcement
analytical
method
00125399
Yes
830.1900
Submittal
of
Sample
Fort
Meade,
MD
Yes
Expires
11/
06/
2013
830.6302
Color
00125399
Yes
Colorless
830.6303
Physical
state
00125399
Yes
Crystalline
solid
mixture
830.6304
Odor
00125399
Yes
830.6313
Stability
to
normal
and
elevated
temperatures,
metals,
and
metal
ions
No
*
Data
Gap
830.7000
pH
No
*
Data
Gap
830.7050
UV/
Visible
absorption
No
*
Data
Gap
830.7200
Melting
point/
melting
range
00125399
Yes
109
º
C
­
115
º
C
830.7220
Boiling
point/
boiling
range
Not
Applicable
830.7300
Density/
relative
density/
bulk
density
00125399
Yes
1.22g/
mL
830.7370
Dissociation
constants
in
water
00125399
Yes
830.7550
Partition
coefficient
(
n­
octanol/
water),
shake
flask
method
No
*
Data
Gap
830.7560
Partition
coefficient
(
n­
octanol
/
water)
generator
column
method
See
Guidelines
830.7550
or
830.7560
or
830.7570
830.7570
Partition
coefficient
(
n­
octanol
/
water)
estimation
by
liquid
chromatography
See
Guidelines
830.7550
or
830.7560
or
830.7570
830.7840
Water
solubility:
column
elution
method;
shake
flask
method
No
*
Data
Gap
830.7860
Water
solubility,
generator
column
method
See
Guidelines
830.7550
or
830.7860
830.7950
Vapor
pressure
00125399
Yes
Less
than
1
mPa
at
20
º
C
RDI:
Branch
Team
Review;
S.
Ary
08/
18/
2005;
S.
Kinard
08/
31/
2005.
