
Page
1
of
6
UNITED
STATES
ENVIRONMENTAL
PROTECTION
AGENCY
WASHINGTON,
D.
C.
20460
OFFICE
OF
PREVENTION,
PESTICIDES
AND
TOXIC
SUBSTANCES
November
22,
2005
MEMORANDUM
SUBJECT:
Triadimefon:
Summary
of
Product
Chemistry
Data
for
Reregistration
Eligibility
Decision
(
RED)
Document.

DP
Barcode:
D315115
PC
Code:
109901
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
byes
Dynamac
Corporation,
The
Dynamac
Building
2275
Research
Boulevard
Rockville,
MD
20850­
3268.
Page
2
of
6
TRIADIMEFON
REREGISTRATION
ELIGIBILITY
DECISION
(
RED)

PRODUCT
CHEMISTRY
CONSIDERATIONS
PC
Code
109901;
Case
No.
2700
DESCRIPTION
OF
CHEMICAL
Triadimefon
[
1­(
4­
chlorophenoxy)­
3,3­
dimethyl­
1­(
1H­
1,2,4­
triazol­
1­
yl)­
2­
butanone]
is
a
triazole
systemic
fungicide
registered
for
treatment
of
mildew
and
rust
diseases
in
apples,
grapes,
pears,
pineapple,
and
raspberries.

Chemical
Structure:
Triadimefon
Empirical
Formula:
C14H16ClN3O2
Molecular
Weight
293.75
grams
Chemistry
Abstract
Service
[
CAS]
Registry
Number:
43121­
43­
3
PC
Code:
109901
IDENTIFICATION
OF
ACTIVE
INGREDIENT
Triadimefon
is
a
colorless
crystalline
solid
with
a
melting
point
of
82
º
C,
density
of
1.23
g/
mL,
noctanol
water
partition
coefficient
(
log
Po/
w)
of
3.11,
and
vapor
pressure
of
0.2
mPa
at
20
º
C.
Triadimefon
is
soluble
in
water
(
64
mg/
L
at
20
º
C),
and
is
moderately
soluble
in
most
organic
solvents
except
aliphatics.

MANUFACTURING­
USE
PRODUCTS
A
search
of
the
Reference
Files
System
(
REFS)
conducted
03/
06/
2000
identified
three
Triadimefon
manufacturing­
use
products
(
MPs)
registered
under
PC
Code
109901:
The
Bayer
Corporation
(
formerly
Mobay
Corporation)
97.7
percent
technical
(
Technical;
EPA
Registration
Number.
3125­
319),
and
50
percent
and
22
percent
formulation
intermediates
(
FIs;
EPA
Registration
Numbers:
Page
3
of
6
3125­
334
and
3125­
376,
respectively).
Triadimefon
is
a
List
B
chemical,
the
Bayer
Corporation's
97.7
percent
Technical/
Technical
Grade
Active
Ingredient
[
T/
TGAI]
is
subject
to
a
reregistration
eligibility
decision.

REGULATORY
BACKGROUND
Product
chemistry
data
originally
reviewed
for
Triadimefon
in
conjunction
with
PP#
2F2665/
FAP#
2H5343/
2F2688/
2F2704
(
RCB
Memorandum,
09/
09/
1982,
A.
Smith).
The
Triadimefon
Phase
4
Review
dated
01/
31/
1991
by
S.
Funk,
determined
that
the
available
product
chemistry
submissions
concerning
product
identity;
discussion
of
formation
of
impurities;
preliminary
analysis;
certified
limits;
color;
physical
state;
odor;
pH;
melting
point;
density;
and
solubility
(
OPPTS
Guideline
Numbers:
830.1550,
830.1670,
830.1700,
830.1750,
830.6302,
830.6303,
830.6304,
830.7000,
830.7200,
830.7300,
and
830.7840)
were
acceptable
for
Phase
5
review.
Additional
data
were
required
for
the
remaining
product
chemistry
requirements
listed
in
Table
1.

The
status
of
the
data
requirements
for
the
Triadimefon
[
T/
TGAI]
is
presented
in
Table
1.
Refer
to
this
table
for
a
listing
of
the
outstanding
data
requirements/
data
gaps.

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

1.
OPPTS
Guideline
830.1670,
Discussion
formation
of
impurities.
2.
OPPTS
Guideline
830.1750,
Upper
certified
limits
not
provided
for
impurities
on
the
confidential
statement
of
formula
[
CSF].
Current
Agency
Policy
requires
that
the
registrant
submit
data
which
demonstrate
that
all
impurities
listed
on
the
confidential
statement
of
formula
[
CSF]
either
are
not
toxicologically
significant
or
submit
a
revised
CSF
with
upper
certified
limits
for
all
impurities
structurally
related
to
the
active
ingredient
and
present
at
greater
than
0.1%.
3.
OPPTS
Guideline
830.1800,
Enforcement
Analytical
Method.
4.
OPPTS
Guideline
830.7050,
UV/
VIS
Absorption.

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
the
OPPTS
830
Series
Guidelines,
the
registrant
must
submit
a
new
complete
updated
Product
Chemistry
Data
Package.

AGENCY
MEMORANDA
CITED
IN
THIS
DOCUMENT
Page
4
of
6
CBRS
Number(
s):
None
DP
Barcode(
s):
None
Subject:
PP#
2F2665/
FAP#
2H5343/
2F2688/
2F2704:
Bayleton
in
Wheat,
Barley,
Pineapples,
and
Grasses.
Evaluation
of
residue
data
and
analytical
method.
From:
A.
Smith
To:
H.
Jacoby
and
Toxicology
Branch
Dated:
09/
09/
1982
MRID(
s):
00098118
and
00098120
CBRS
Number(
s):
8566
and
9929
DP
Barcode(
s):
D168542
and
D178884
Subject:
Triadimefon
(
109901):
Storage
Stability
Data,
PAM
I
Multiresidue
Methods,
Product
Chemistry
Data.
From:
S.
Hummel
To:
M.
Wilhite/
B.
Sidwell
Dated:
12/
22/
1992
MRID(
s):
42307801­
42307803
CBRS
Number(
s):
RD
Memorandum
DP
Barcode(
s):
D232412
Subject:
Product
Chemistry
Review
of
Bayleton
Technical
From:
A.
Smith
To:
R.
Kearns
Dated:
03/
14/
1997
MRID(
s):
44166001
PRODUCT
CHEMISTRY
CITATIONS
Bibliographic
citations
include
only
master
record
identification(
s)
[
MRIDs]
containing
data,
which
fulfill
the
data
requirements.

References
(
cited):

MRID
00098119
Smith,
D.
N.
(
1981)
Bayleton
Manufacture.
(
Unpublished
study
received
Mar
30,
1982
under
2F2665;
submitted
by
Mobay
Chemical
Corp.,
Kansas
City,
Mo.;
CDL:
070747­
A)

MRID
00098120
Harbin,
D.
N.;
Slahck,
S.
C.;
Westphal,
C.
(
1982)
The
Composition
of
Technical
Bayleton:
Report
No.
80605.
(
Unpublished
study
received
Mar
30,
1982
under
2F2665;
submitted
by
Mobay
Chemical
Corp.,
Kansas
City,
Mo.;
CDL:
070747­
B)

MRID
40477401
Talbot,
T.
(
1987)
Supplement
1:
Product
Chemistry
of
Bayleton
Technical:
Laboratory
Project
ID
ANR­
00587.
Unpublished
study
prepared
by
Mobay
Corporation.
55
p.
Page
5
of
6
MRID
41616001
Talbot,
T.
(
1990)
Product
Chemistry
of
Bayleton
Technical:
Supplement
1:
Lab
Project
Number:
80298;
85997;
91321.
Unpublished
study
prepared
by
Mobay
Corp.
25
p.

MRID
42307801
Fontaine,
L.
(
1992)
Supplemental
Product
Chemistry
of
Bayleton
Technical:
Lab
Project
Number:
MCL0054.
Unpublished
study
prepared
by
Miles,
Inc.
22
p.

MRID
42307802
Fontaine,
L.
(
1992)
Supplemental
Product
Chemistry
of
Bayleton
Technical:
Lab
Project
Number:
ANR­
00692:
ANR­
00792.
Unpublished
study
prepared
by
Miles,
Inc.
20
p.

MRID
42307803
Fontaine,
L.
(
1992)
Supplemental
Product
Chemistry
of
Bayleton
Technical:
Lab
Project
Number:
52834:
68665:
85997.
Unpublished
study
prepared
by
Miles,
Inc.
41
p.

MRID
44166001
Fontaine,
L.
(
1996)
Product
Chemistry
of
Bayleton
Technical:
Lab
Project
Number:
107296:
107241:
99642.
Unpublished
study
prepared
by
Bayer
Corp.
173
p.
Page
6
of
6
Table
1
:
Product
Chemistry
Data
Summary
for
Triadimefon
OPPTS
Guideline
Number
Requirements:
Triadimefon
[
Technical
]

CAS
No.:
43121­
43­
3
PC
Code:
109901
Formula:
C14H16ClN3O2
Data
Requirements
Completed
Results
or
*
Data
Gap
Master
Record
ID
[
MRID]
or
Reference
830.1550
Product
identity
and
composition
Yes
CSF
Oct.
16­
17,
1996
830.1600
Description
of
materials
used
to
produce
the
product
Yes
00098119,
423078­
01
830.1620
Description
of
production
process
Yes
00098119,
423078­
01
830.1650
Description
of
formulation
process
Yes
00098119,
423078­
01
830.1670
Discussion
of
formation
of
impurities
No
*
Data
Gap
(
impurities)

830.1700
Preliminary
analysis
Yes
00098120,
441660­
01
830.1750
Certified
limits
No
*
Data
Gap
(
impurities)

830.1800
Enforcement
analytical
method
No
*
Data
Gap
(
impurities)

830.1900
Submittal
of
Sample
Yes
Expires
05/
2007
EPA,
Ft.
Meade,
MD
830.6302
Color
Yes
Colorless
416160­
01
830.6303
Physical
state
Yes
Crystalline
solid
416160­
01
830.6304
Odor
Yes
Odorless
to
musty
416160­
01
830.6313
Stability
to
normal
and
elevated
temperatures,
metals,
and
metal
ions
Yes
Compatible
w/
materials
tested
423078­
03
830.7000
pH
Yes
5.5
in
a
1%
suspension
416160­
01
830.7050
UV/
Visible
absorption
No
*
Data
Gap
830.7100
Viscosity
Not
Applicable
830.7200
Melting
point/
melting
range
Yes
82.3
º
C
416160­
01
830.7220
Boiling
point/
boiling
range
See
Guideline
830.7200
830.7300
Density/
relative
density/
bulk
density
Yes
1.23
g/
mL
416160­
01
830.7370
Dissociation
constants
in
water
Not
Applicable
830.7550
Partition
coefficient
(
n­
octanol/
water),
shake
flask
method
Yes
log
Po/
w
of
3.11
at
22
º
C
423078­
03
830.7560
Partition
coefficient
(
n­
octanol
/
water)
generator
column
method
See
Guideline
830.7550
830.7570
Partition
coefficient
(
n­
octanol
/
water)
estimation
by
liquid
chromatography
See
Guideline
830.7550
830.7840
Water
solubility:
column
elution
method;
shake
flask
method
Yes
64
mg/
L
at
20
º
C
416160­
01
830.7860
Water
solubility,
generator
column
method
See
Guideline
830.7840
0.2
mPa
at
20
º
C
830.7950
Vapor
pressure
Yes
0.6
mPa
at
25
º
C
423078­
01
RDI:
Branch
Team
Review;
S.
Ary
(
08/
17/
2005);
S.
Kinard
(
08/
19/
2005)
