Document ID: EPA-HQ-OPP-2007-0312-0004
Agency: epa
Document Type: Supporting & Related Material
Title: 
Posted Date: 2009-06-03T04:00Z

UNITED STATES ENVIRONMENTAL PROTECTION AGENCY

WASHINGTON, D.C.  20460

OFFICE OF           

PREVENTION, PESTICIDES

AND TOXIC SUBSTANCES

MEMORANDUM

	Date:	12/7/07

	Subject:	Triflumizole.  Petition for Registration of use on Brassica
Leafy Greens (Subgroup 5B).  Summary of Analytical Chemistry and Residue
Data.  Petition Number 7E7183

DP Nums:	338653, 341963	Decision Number:	374869

PC Code:	128879	MRID Nos.:	47054101

40 CFR 180.	476

Chemical Class:	Imidazole Fungicide

	From:	J. R. Tomerlin, PhD., Plant Pathologist

		Alternative Risk Integration Assessment (ARIA) Team

		Fungicide Branch/Registration Division (FB/RD, 7505P)

	Through:	William Cutchin, Chemist, ARIA Team

		Risk Integration, Minor Use, and Emergency Response Branch (RIMUERB)

		Registration Division (RD, 7505P)

		Dana Vogel, Branch Chief

		Registration Action Branch 1/Health Effects Division (RAB1/HED, 7509P)

	To:	Barbara Madden, Minor Use Team Leader

		RIMUERB/RD (7505P)

This document was originally prepared under contract by Dynamac
Corporation (1910 Sedwick Road, Building 100, Suite B, Durham NC 27713;
submitted 08/24/2007).  The Alternative Risk Integration and Assessment
(ARIA) team reviewed the document and revised it to reflect current
Office of Pesticide Programs (OPP) policies.

Executive Summary

Triflumizole is a broad spectrum, imidazole fungicide (Group 3) used for
the control of fungal diseases on a variety of fruit crops, cucurbit
vegetables, hazelnuts, and pineapple seed pieces.    SEQ CHAPTER \h \r 1
Permanent tolerances are established for the combined residues of
triflumizole and its metabolites containing the FA-1-1 moiety (IUPAC
name 4-chloro-2-trifluoromethylaniline), calculated as parent, in/on
various crops at levels ranging from 0.05 parts per million (ppm) on
filberts to 15 ppm in grape pomace [40 CFR §180.476(a)(1)].  Tolerances
are also established for the combined residues of triflumizole,
4-chloro-2-hydroxy-6-trifluoromethylaniline sulfate, and other
metabolites containing the FA-1-1 moiety, calculated as parent, in
livestock commodities [40 CFR §180.476(a)(2)].  In addition,
time-limited tolerances are established on various Brassica vegetables,
Swiss chard, and dandelion in conjunction with Section 18 emergency
uses.

In the U.S., triflumizole is registered to Chemtura USA Corporation for
use on food/feed crops under the trade name Procure® and is formulated
as 50% water soluble packets (WS), 50% water dispersible granules (WDG),
and as 480SC (suspension concentrate) at approximately 42% active
ingredient (ai).  Interregional Research Project No. 4 (IR-4) has
submitted a petition proposing the use of triflumizole (SC) on Brassica
leafy greens as multiple broadcast foliar applications at up to 0.25 lb
ai/A per application at a minimum retreatment interval (RTI) of 7 days,
for a maximum of 1.0 lb ai/A per season.  Applications may be made with
ground or air equipment in a minimum of 10 gallons per acre (gal/A) and
a 1-day preharvest interval (PHI) is specified.  In conjunction with
this use, IR-4 has proposed the following permanent tolerance for
triflumizole:

Vegetable, Brassica leafy, subgroup 5B	20.0 ppm

  SEQ CHAPTER \h \r 1 The nature of the residue is adequately understood
based on acceptable metabolism data on apples, cucumbers, grapes, and
pears.  The residues of concern are triflumizole and its metabolites
containing the 4-chloro-2-trifluoromethylaniline moiety.

As the crop uses being purposed in this petition do not include any
regulated livestock feedstuffs, issues pertaining to livestock
metabolism, analytical methods and storage stability data for animal
commodities, and residues in livestock commodities are not relevant to
the current petition.

An adequate gas chromatograph/nitrogen-phosphorus detection (GC/NPD)
method is available (Method I in PAM Vol. II) for enforcing tolerances
of triflumizole in plant commodities.  This common moiety method
involves alkaline hydrolysis of parent and its metabolites to FA-1-1,
which is then distilled and partitioned into hexane.  Residues of FA-1-1
are purified using a silica gel column and determined by GC/NPD. 
Residues are expressed in terms of triflumizole, and the method limit of
quantitation (LOQ) is 0.5 ppm for plant commodities.

Samples from the mustard greens field trials were analyzed for the
combined residues of triflumizole and its metabolites convertible to
FA-1-1 using a GC/mass selective detection (MSD) method (CG/MSD, Morse
Method Meth-115, Revision #3), which was derived from the tolerance
enforcement method.  For this method, residues are converted to FA-1-1
by refluxing under acidic and then basic conditions, and FA-1-1 is then
distilled and partitioned into hexane.  Following cleanup using a silica
solid phase extraction (SPE) cartridge, residues of FA-1-1 are
determined by GC/MSD and expressed in parent equivalents.  The
statistically calculated LOQ for parent was 0.04 ppm, and the limit of
detection (LOD) was 0.01 ppm.  This method was adequately validated
prior to and in conjunction with the analysis of field trial samples.

  SEQ CHAPTER \h \r 1 Adequate storage stability data are available
indicating that triflumizole is stable under frozen storage conditions
for up to 12 months in apples, grapes, and cherries, 10 months in
cucurbit vegetables and strawberries, and 3.2 months in filberts. 
However, in a stability study conducted concurrently with the mustard
greens field trials, combined triflumizole residues were shown to
decline on average by 44% in mustard greens stored at -20ºC for 9.5
months, or 0.15% per day.  Based on these data, the combined residues
in/on mustard greens were corrected for potential declines during frozen
storage, according to the equation RS = RF ÷ (1 – (0.0015 x DAYS)),
where RS is the starting residue concentration, RF is the final residue
concentration, and DAYS is the number of days in storage.

The mustard green field trial data are adequate and support the use of
triflumizole on Brassica leafy greens.  An adequate number of tests were
conducted in the appropriate geographical regions at approximately the
1x use rate, and samples were analyzed for residues of concern using an
adequate method.  Although the field trials were conducted using a 50%WS
formulation and the proposed label directions specify an approximate 42%
WS formulation, study treatments were applied appropriately in lb ai/A. 
The difference in formulations is not expected to have a significant
impact on the magnitude of the residues.

Following four broadcast foliar applications of triflumizole (50%WS)
totaling 0.99-1.02 lb ai/A (approximate 1x rate), the uncorrected
combined residues were 0.99-17.90 ppm in/on 20 samples of mustard greens
harvested at 1 day after the last treatment (DAT).  The average
uncorrected residues were 6.84 ppm and the highest average field trial
(HAFT) residues were 15.45 ppm.  When residues are corrected for
potential declines of 0.15%/day during frozen storage, the combined
residues are 1.09-20.27 ppm in/on mustard greens, and the average and
HAFT residues are 7.72 and 17.50 ppm, respectively.  Data from a residue
decline test also indicated that the combined residues declined rapidly
from 0 to 1 DAT, and then declined more slowly from 1 to 6 DAT.

Adequate confined and field rotational crop studies are available to
support the rotational crop restrictions specified on current and
proposed labels.  

  SEQ CHAPTER \h \r 1 Regulatory Recommendations and Residue Chemistry
Deficiencies

No major deficiencies were noted in the subject petition that would
preclude establishing a permanent tolerance for triflumizole residues on
Brassica leafy greens.  Therefore, ARIA recommends establishing a
permanent tolerance for the combined residues of triflumizole and its
metabolites convertible to FA-1-1, expressed as parent, in/on Brassica
leafy greens (subgroup 5B) at 40 ppm.  A human health risk assessment
for triflumizole is forthcoming.  

Although IR-4 proposed a tolerance of 20 ppm, the residue data submitted
with the petition results in a calculated tolerance value of 40 ppm. 
Therefore, the registrant must be instructed to submit a revised Section
F requesting a tolerance of 40 ppm in/on Vegetable, Brassica leafy,
subgroup 5B.

NOTE TO PM: The following current 20 ppm tolerances on some individual
commodities of crop subgroup 5B will be superceded by the recommended
crop group tolerance of 40 ppm and should be deleted from 40 CFR
180.476: collards, kale; mustard greens, and turnip greens.

NOTE TO PM: The tolerance listing for   SEQ CHAPTER \h \r 1 triflumizole
currently includes tolerances on grape pomace (15 ppm) and grape, raisin
waste (10 ppm).  These commodities are no longer regulated livestock
feedstuffs and the registrant should be advised to petition the Agency
to delete them from 40 CFR §180.476.  In addition, the registrant
should be advised that the current tolerance on apple pomace (2 ppm) is
based on the processing factor for dry apple pomace.  As the apple
processing study indicates that residues do not concentrate in wet apple
pomace; , a separate tolerance on apple pomace is not necessary and the
registrant should also be advised to petition the Agency for the
deletion of the tolerance on apple pomace.

NOTE TO PM: With regards to tolerances for animal commodities, apples
are the only crop with registered triflumizole uses that also have a
regulated livestock feedstuff (wet apple pomace).  As wet apple pomace
is not fed to either poultry or swine, there is no potential for
transferring triflumizole residues to poultry or swine commodities. 
Therefore, the registrant should be advised to petition the Agency for
deletion of the current tolerances on eggs; poultry fat, meat, and meat
byproducts; and hog fat, meat and meat byproducts.  In addition, the
registrant should be advised to petition the Agency to reevaluate the
current tolerances on cattle, horse, goat and sheep commodities as the
deletion of grape pomace and raisin waste may substantially reduce the
dietary exposure of cattle to triflumizole.  

Background

Triflumizole is a broad spectrum, imidazole fungicide (group 3) that
inhibits ergosterol biosynthesis in fungi.  It is used for the control
of powdery mildew, leaf spot, scab and various blights, rusts and rots. 
In the U.S., triflumizole is registered to Chemtura USA Corporation and
is marketed under the trade name Procure® for use on food/feed crops. 
It is approved for broadcast foliar applications to apples, pears,
cherries, cucurbit vegetables, grapes, strawberries and hazelnuts, and
for pre-plant treatment of pineapple seed pieces.  Section 18 emergency
exemptions have also been approved for foliar uses on various Brassica
vegetables, Swiss chard and dandelions.

Table 1: Nomenclature for Triflumizole and its Common Analyte

Chemical structure	

Common name	Triflumizole

IUPAC1 name
(E)-4-chloro-α,α,α-trifluoro-N-(1-imidazol-1-yl-2-propoxyethylidene)-
o-toluidine

CAS2 name
1-[(1E)-1-[[4-chloro-2-(trifluoromethyl)phenyl]imino]-2-propoxyethyl]-1H
-imidazole

CAS registry number	68694-11-1

End-use products (EPs)	Procure® 50WS; EPA Reg. No. 400-431

Procure® 480SC; EPA Reg. No. 400-518

Metabolite structure	

Common name	FA-1-1

IUPAC name	4-chloro-2-trifluoromethylaniline

1 IUPAC = International Union of Pure and Applied Chemistry

2 CAS = Chemical Abstracts Service

Table 2: Physicochemical Properties of Triflumizole

Parameter	Value	Reference

Melting point/range	63.5 degrees Celsius ((C)	DEB# 6410, J. Smith,
1/7/92

pH	Not available (NA)

	Bulk Density	0.50-0.70 (at 20ºC)

	Water solubility (grams/liter (g/L) at 20ºC)	0.0125 (at pH 5.9)

	Solvent solubility (grams per 100 milliliters (g/100 mL) at 20ºC)
Chloroform	222

Acetone	144

n-Hexane	1.76

Methanol	49.6

Xylene	63.9

	Vapor pressure (at 25ºC)	1.4 x 10-6 millimeters of mercury (mmHg) 

	Dissociation constant, pKa	3.7

	Octanol/water partition coefficient, Log(KOW) at 25ºC	25

	UV/visible absorption spectrum	NA

	

860.1200  Directions for Use

The proposed use patterns on Brassica leafy greens are summarized in
Table 3.

Table 3: Summary of Directions for Use of Triflumizole (Procure 480SC)

Applic. Timing, Type, and Equip. 1	Formulation

[EPA Reg. No.]	Applic. Rate 

(lb ai/A)	Max. No. Applic. per Season	Max. Seasonal Applic. Rate

(lb ai/A)	PHI

(days)	Use Directions and Limitations 2

Brassica Leafy Greens 3

Broadcast foliar application, at first indication of disease, using
ground or air equipment	4 lb/gal SC

[400-518]	0.125-0.25	4	1.0	1	A minimum RTI of 7 days is specified.  

Apply in a minimum of 10 gal/A for ground applications.

1	Do not apply through irrigation systems.

2	Rotational crops restrictions of 30 days are specified for leafy and
fruiting vegetables and 60 days for bulb and root vegetables.  Do not
plant small cereal grains, cotton and all other crops not listed on the
label for one year after application. 

3	Broccoli raab, Chinese cabbage (bok choy), collards, kale, mizuna,
mustard greens, mustard spinach, and rape greens (including all
cultivars and/or hybrids of these).

Conclusions.  The label directions are adequate to allow evaluation of
the residue data relative to the proposed use.  

860.1300 Nature of the Residue - Plants

  SEQ CHAPTER \h \r 1 The nature of the residue in plants is adequately
understood for purposes of this petition on Brassica leafy greens. 
Acceptable metabolism data are available on apples, cucumbers, grapes,
and pears (PP#5G3232, N. Dodd, 7/3/85).  The Agency determined that the
residues of concern include triflumizole and its metabolites containing
the 4-chloro-2-trifluoromethyaniline moiety (calculated as
triflumizole).  This conclusion was reaffirmed in a meeting of the
Metabolism Assessment Review Committee (MARC) on 2/26/02 (D280869, J.
Tyler, 3/13/02).  

860.1300 Nature of the Residue - Livestock

There are no livestock feedstuffs associated with the proposed use on
mustard greens.  Therefore, data requirements for livestock metabolism
are not relevant to this tolerance petition.    

860.1340 Residue Analytical Methods

An adequate GC/NPD method is available (Method I in PAM Vol. II, section
180.476) for determining the combined residues of triflumizole and its
metabolites containing the FA-1-1 moiety in plant commodities (G.
Kramer, 12/16/94).  This common moiety method involves alkaline
hydrolysis of parent and its metabolites to FA-1-1 coupled with
distillation of FA-1-1 into hexane.  Residues are filtered through
anhydrous sodium sulfate, purified using a silica gel SPE column, and
determined as FA-1-1 by GC/NPD.  Residues are expressed in terms of
triflumizole.  The method LOQ is 0.5 ppm for plant commodities.

Samples from the current mustard greens field trials were analyzed for
the combined residues of triflumizole and its metabolites convertible to
FA-1-1 using a GC/MSD method (Morse Laboratories Analytical Method
Meth-115, Revision #3).  This method is derived from the current
tolerance enforcement method and is a more recent version of a method
previously deemed adequate for collecting residue data on strawberries
(DP Num: 274589, J. Tyler, 3/11/02).

For the GC/MSD method, samples were refluxed with dilute acetic
acid/sodium nitrate for 90 minutes.  While still refluxing, 20% sodium
hydroxide (NaOH) was slowly added and refluxing was continued for an
additional 90 minutes.  At completion of the reflux, the contents of the
flask were distilled into a flask containing hexane.  The
distillate/hexane fraction was acidified, and residues were partitioned
into the hexane and concentrated.  Residues were then cleaned up using a
silica SPE cartridge eluted with ethyl acetate.  Residues of FA-1-1 were
determined by GC/MSD, using the mass to charge ratio (m/z) 173 and 195
ions for quantitation.  Residues are expressed in parent equivalents. 
The statistically calculated LOQ for parent was 0.04 ppm, and the LOD
was 0.01 ppm.  The lowest limit of method validation (LLMV) was 0.05
ppm.

  SEQ CHAPTER \h \r 1 Based on acceptable concurrent method recovery
data, the analytical method is adequate for data collection.

860.1360 Multiresidue Methods

Data are available on the recovery of triflumizole through FDA
Multiresidue Method Testing Protocols.  The FDA PESTDATA database, dated
06/2005 (PAM Vol. I, Appendix I), indicates that triflumizole is
completely recovered using Multiresidue Method Section 302 (Protocol D)
without cleanup, but information was not listed for Methods 303 and 304.

860.1380 Storage Stability

  SEQ CHAPTER \h \r 1 Adequate storage stability data are available
indicating that triflumizole is stable under frozen storage conditions
for up to 12 months in apples, grapes, and cherries (PP#6F3372, S.
Malak, 1/25/90; and DP Num: 242429, J. Tyler, 3/11/02), 10 months in
cucurbit vegetables and strawberries (DP Num: 271003, J. Tyler, 3/11/02;
and DP Num: 274589, J. Tyler, 3/11/02), and 3.2 months in filberts (DP
Num: 312293, J. Tyler, 5/18/05).

A storage stability study was conducted in conjunction with the
submitted mustard greens field trials.  For this study, control samples
of mustard greens were fortified separately with triflumizole and its
metabolites, FM-6-1 and FA-1-1, each at 5.0 ppm, and stored under the
same conditions (-20ºC) as the field trial samples.  At the end of the
analytical phase, the stored samples were analyzed in triplicate along
with a control sample and samples freshly fortified with each analyte. 
The average recoveries from the stored samples, corrected for concurrent
recoveries, were 70%, 55% and 44% for parent, FM-6-1, and FA-1-1,
respectively.  These recoveries correlate to declines of 30-56% over 9.5
months of storage and indicate that there is the potential for residue
decline in frozen mustard greens.  Because the method converts parent
and all metabolites to a common moiety, corrections for declines in
individual residues can not be made.  Therefore, residue values should
be corrected based on the average decline of 44% over 9.5 months
(0.15%/day decrease) according to the equation RS = RF ÷ (1 – (0.0015
x DAYS)), where RS is the starting residue concentration, RF is the
final residue concentration, and DAYS is the number of days in storage. 

In the submitted mustard greens field trials, samples were held in
storage at -20ºC for 16-213 days  (≤7 months) prior to extraction for
analysis.  Corrected residues were calculated using the actual storage
interval for each sample and a decline factor of 0.15%/day.

Conclusions.  The available storage stability data are adequate. 
Although all earlier studies indicated that triflumizole is stable under
frozen storage in plant commodities, none of these studies included a
leafy or forage type matrix.  The data on mustard greens indicates that
residues may decline by 0.15% per day in mustard greens; therefore,
residues in/on mustard greens should be corrected for potential declines
during frozen storage.

860.1400 Water, Fish, and Irrigated Crops

This guideline requirement is not relevant to the current petition as no
aquatic uses are being proposed. 

860.1460 Food Handling

This guideline requirement is not relevant to the current petition as no
food handling uses are being proposed for triflumizole. 

860.1480 Meat, Milk, Poultry, and Eggs

As there are no livestock feedstuffs associated with the proposed crop
uses, data requirements pertaining to meat, milk, poultry, and eggs are
not relevant to this tolerance petition.

860.1500 Crop Field Trials

47054101.der.doc, J. R. Tomerlin, @@date

IR-4 submitted field trial data on mustard greens to support the
proposed use of triflumizole (SC) on Brassica leafy greens.    SEQ
CHAPTER \h \r 1 The results from these studies are discussed below and
the residue data are summarized in Table 4.

Table 4: Summary of Residue Data from Crop Field Trials with
Triflumizole

Crop matrix	Total Applic. Rate (lb ai/A)	PHI (days)	Residue Levels (ppm)
1

	n	Min.	Max.	HAFT 2	Median	Mean	Std. Dev.

Mustard Greens (proposed use = 1.0 lb ai/A total application rate, 1-day
PHI)

Mustard Greens	0.99-1.02	1	20	0.99	17.90	15.45	4.61	6.84	4.83

1.09 3	20.27	17.50	5.53	7.72	5.40

1 The method converts all metabolites into the common moiety, FA-1-1. 
The statistically calculated LOQ was 0.04 ppm.

2 HAFT = highest average field trial residues.

3 The bolded values were determined using residue data corrected for
declines of 0.15%/day during frozen storage according to the equation RS
= RF ÷ (1 – (0.0015 x DAYS)), where RS is the starting residue
concentration, RF is the final residue concentration, and DAYS is the
number of days in storage.

Mustard greens.  In ten field trials conducted in Zones 2, 3, 4, 5, 6,
and 10 during 2004, triflumizole (50%WS) was applied to mustard greens
as four broadcast foliar applications, beginning approximately 28 days
before normal maturity, at 0.24-0.26 lb ai/A/application and RTIs of
6-10 days, for a total of 0.99-1.02 lb ai/A (approximate 1x rate). 
Applications were made using ground equipment in volumes of 20-46 gal/A,
and did not include the use of any spray adjuvants.  Single control and
duplicate treated samples of mature mustard green leaves were collected
at each site at 1 DAT.  Samples were also collected a 0, 1, 4, and 6 DAT
from one site to assess residue decline.  In addition, samples were
collected at one other site 1, 3, and 7 DAT; however, only data for 1
DAT from that site are addressed in the study report.

Samples were stored frozen for up to 213 days (7 months) prior to
extraction for analysis.  Based on the results of the concurrent storage
stability study, residues of parent and the metabolites FM-6-1 and
FA-1-1 were shown to decline over 9.5 months of frozen (-20ºC) storage
by 30%, 45% and 56%, respectively.  As the analytical method converts
parent and all metabolites to a common moiety, an average decline of
0.15% per day was used to correct residue values according to the
equation RS = RF ÷ (1 – (0.0015 x DAYS)), where RS is the starting
residue concentration, RF is the final residue concentration, and DAYS
is the number of days in storage.

 

The GC/MSD method used to determine the combined residues of
triflumizole and its metabolites convertible to FA-1-1 was adequately
validated prior to and in conjunction with the analysis of field trial
samples.  The statistically calculated LOQ for parent was 0.04 ppm, and
the calculated LOD was 0.01 ppm.  The LLMV is 0.05 ppm.

Following four broadcast foliar applications of triflumizole (SC)
totaling 0.99-1.02 lb ai/A, the combined residues (uncorrected for
storage decline) were 0.99-17.9 ppm in/on 20 samples of mustard greens
harvested 1 DAT.  The average uncorrected residues were 6.84 ppm and the
HAFT residues were 15.45 ppm.  When corrected for potential declines of
0.15%/day during storage, combined residues in/on all 20 samples were
1.09-20.27 ppm, average residues were 7.72 ppm, and the HAFT residues
were 17.50 ppm.  

Data from the residue decline test indicated that the combined residues
declined rapidly from 0 to 1 DAT, and then declined more slowly from 1
to 6 DAT.

Conclusions.  The mustard green field trials are adequate and support
the use of triflumizole on Brassica leafy greens.  An adequate number of
tests were conducted in the appropriate geographical regions, and
samples were analyzed for residues of concern using an adequate method. 

860.1520 Processed Food and Feed

There are no processed commodities associated with mustard greens. 
Therefore, data requirements for processed food and feed are not
relevant to this tolerance petition.

  SEQ CHAPTER \h \r 1 860.1650 Submittal of Analytical Reference
Standards

An analytical reference standard for triflumizole is currently available
at the EPA National Pesticide Standards Repository.

860.1850/1900 Confined and field Accumulation in Rotational Crops

Adequate   SEQ CHAPTER \h \r 1 confined and limited field rotational
crop studies were submitted in conjunction with a tolerance petition for
use of triflumizole on strawberries (PP#1F06297, DP Num: 274589, J.
Tyler, 3/11/02; DP Num: 327173, J. Tyler, 1019/06).  Based on the
results of the confined study, the MARC (meeting 2/26/02) concluded that
the residues of concern in rotational crops include triflumizole and all
metabolites containing the FA-1-1 moiety for purposes of risk assessment
and the tolerance expression.  Results from the limited rotational crop
field trials also indicated that the   SEQ CHAPTER \h \r 1 following
plant-back intervals are appropriate for rotated crops:  30 days for
leafy and fruiting vegetables; 60 days for root and tuber vegetables;
and 1 year for cotton, small cereal grains, and any other crops without
registered uses for triflumizole.  The above plant-back intervals are
specified on the current labels; therefore, no plant-back restrictions
are currently required.

860.1550 Proposed Tolerances

The Agency has determined that the residues of concern for plant
commodities include triflumizole and its metabolites containing the
FA-1-1 moiety.    SEQ CHAPTER \h \r 1 Permanent tolerances are
established under 40 CFR §180.476(a)(1) for the combined residues of
triflumizole and its metabolites containing the FA-1-1 moiety,
calculated as parent, in/on various crop at levels ranging from 0.05 ppm
in/on filberts to 15 ppm in/on grape pomace.  Tolerances for livestock
commodities are established under 40 CFR §180.476(a)(2) for the
combined residues of triflumizole,
4-chloro-2-hydroxy-6-trifluoromethylaniline sulfate, and other
metabolites containing the FA-1-1 moiety, calculated as parent, at
levels ranging from 0.05 ppm in eggs, milk, and meat to 0.5 ppm in fat. 
In conjunction with Section 18 uses, time-limited tolerances are also
established under 40 CFR § 180.476(b) at 1 ppm on broccoli, 7 ppm on
Swiss chard and dandelion leaves, and at 20 ppm on various types of
Brassica leafy greens.  These tolerances are set to expire on 12/31/09.

The data submitted with the petition were used with the MRL Calculator
spreadsheet to determine a tolerance value of 40 ppm (Attachment I)
rather than the value of 20 ppm proposed by the petitioner.  

The proposed and recommended tolerances for the Brassica leafy green
subgroup 5B are listed in Table 5.  An adequate number of mustard green
field trials were conducted at the 1x rate to support a permanent
tolerance on Brassica leafy greens.  The Agency’s Guidelines for
Setting Pesticide Tolerances Based on Field Trial Data were utilized for
determining the appropriate tolerance level for the subgroup (Appendix
I), and potential tolerances were calculated using the uncorrected and
corrected residue data; however, only tolerance calculations using
corrected data are reported here.  Based on the residue data corrected
for storage declines, the calculated tolerance is 40 ppm for the
Brassica leafy greens (subgroup 5B).  

NOTE TO PM: The following current 20 ppm tolerances on some individual
commodities of crop subgroup 5B will be superceded by the recommended
crop group tolerance of 40 ppm and should be deleted from 40 CFR
180.476: collards, kale; mustard greens, and turnip greens.

NOTE TO PM: The tolerance listing for   SEQ CHAPTER \h \r 1 triflumizole
currently includes tolerances on grape pomace (15 ppm) and grape, raisin
waste (10 ppm).  These commodities are no longer regulated livestock
feedstuffs and the registrant should be advised to petition the Agency
to delete them from 40 CFR §180.476.  In addition, the registrant
should be advised that the current tolerance on apple pomace (2 ppm) is
based on the processing factor for dry apple pomace.  As the apple
processing study indicates that residues do not concentrate in wet apple
pomace; , a separate tolerance on apple pomace is not necessary and the
registrant should also be advised to petition the Agency for the
deletion of the tolerance on apple pomace.

NOTE TO PM: With regards to tolerances for animal commodities, apples
are the only crop with registered triflumizole uses that also have a
regulated livestock feedstuff (wet apple pomace).  As wet apple pomace
is not fed to either poultry or swine, there is no potential for
transferring triflumizole residues to poultry or swine commodities. 
Therefore, the registrant should be advised to petition the Agency for
deletion of the current tolerances on eggs; poultry fat, meat, and meat
byproducts; and hog fat, meat and meat byproducts.  In addition, the
registrant should be advised to petition the Agency to reevaluate the
current tolerances on cattle, horse, goat and sheep commodities as the
deletion of grape pomace and raisin waste may substantially reduce the
dietary exposure of cattle to triflumizole.  

There are no Codex MRLs established for residues of triflumizole
(Appendix II).  However, Canada and Mexico have established MRL for
triflumizole residues in a number of fruit and/or vegetable crops, but
neither country has established or proposed MRLs for Brassica leafy
greens.  Several other countries (Netherlands, Spain, Brazil, Japan,
Korea, and Australia) also have established MRLs for residues of
triflumizole in a variety of fruit and vegetable crops.  These include
MRLs in the Netherlands and Spain for residues on Brassica leafy
vegetables at 0.05 mg/kg.

Table 5. Tolerance Summary for Triflumizole

Commodity	Proposed/Current Tolerance (ppm)	Recommended Tolerance (ppm)
Comments; Correct Commodity Definition

Vegetable,  Brassica leafy, Group 5B	20	40	Adequate data are available
on mustard greens to support a tolerance on Brassica leafy greens, Group
5B

Cabbage, chinese	20	Delete	Once a tolerance on Brassica leafy greens
(subgroup 5B) is established, the existing separate, time-limited
tolerances on members of this subgroup can be deleted.

Collards	20

Kale	20

Mustard, greens	20

References

DEB#:	6410

Subject:	I.D. No. 400-UGA. Triflumizole.  Registration of A815
Technical.

From:	J. Smith

To:	B. Chambliss

Dated:	1/7/92

MRID(s):	45375403-45375406

DP Number:	None

Subject:	PP #6F3372/FAP#6H5497.  Triflumizole (Procure 50W®) in or on
Various RACs and Animal Commodities.  (Request for Entry of the Proposed
Enforcement Methods into PAM II)

From:	G. Kramer

To:	A. Marcotte

Dated:	12/16/94

MRID(s):	None

DP Number:	242429

Subject:	PP# 8F4938. Triflumizole in/on Cherries.  Evaluation of Residue
Data and Analytical Methods. 

From:	J. Tyler

To:	M. Waller/ S. Gardner-Jenkins

Dated:	4/30/01

MRID(s):	44438401 and 44438402

DP Number:	274589

Subject:	PP# 1F06297. Triflumizole in/on Strawberries.  Evaluation of
Residue Data and Analytical Methods. 

From:	J. Tyler

To:	M. Waller/ S. Gardner-Jenkins

Dated:	3/11/02

MRID(s):	45375403-45375406

DP Number:	271003

Subject:	PP# 0F6077. Triflumizole in/on Cucurbits.  Evaluation of
Residue Data and Analytical Methods. 

From:	J. Tyler

To:	M. Waller/ S. Gardner-Jenkins

Dated:	3/11/02

MRID(s):	44971301-44971303

DP Number:	280869

Subject:	Briefing to MARC (for meeting on 2/26/02) 

From:	 J. Tyler

To:	Y. Donovan

Dated:	3/13/02

MRID(s):	None

  SEQ CHAPTER \h \r 1 DP Number:	327173

Subject:	Triflumizole.  Label Amendment Request and Review of Limited
Field Rotational Study Submitted in Response to HED-Memoranda Dated
3/11/02.

From:		 J. Tyler

To:		Tamue Gibson/Mary Waller

Dated:		10/19/02

MRID(s):	46728501

DP Number:	312293

Subject:	Triflumizole. Section 3 Request for Use on Filberts. Summary of
Analytical Chemistry and Residue Data. 

From:	J. Tyler

To:	S. Jackson/ R. Forrest

Dated:	5/18/05

MRID(s):	45810201

DP Number:	312293

Subject:	PP#s 1F06297 and 0F06077. Triflumizole.  Label Amendment
Request and Review of Limited Field Rotational Study Submitted in
Response to HED-Memoranda Dated 3/11/02. 

From:	J. Tyler

To:	T. Gibson/ M. Waller

Dated:	10/19/06

MRID(s):	45810201

  SEQ CHAPTER \h \r 1 Attachments: 

Appendix I - Tolerance Assessment Calculations

Appendix II – International Residue Limit Status sheet

Template Version September 2005

Appendix  I - Tolerance Assessment Calculations

The Agency’s Guidance for Setting Pesticide Tolerances Based on Field
Trial Data was utilized for determining the appropriate tolerance level
on Brassica leafy greens.  The datasets used to establish the tolerance
on Brassica leafy greens consisted of mustard greens field trial data
representing applications of a WS formulation at 1x the maximum proposed
use rate.  As specified by the Guidance for Setting Pesticide Tolerances
Based on Field Trial Data SOP, the field trial application rates were
within 25% of the maximum label application rate, and the PHIs were
consistent with the appropriate stage of maturity and the proposed PHI
for Brassica leafy greens.  Only corrected (for storage decline)
residues are provided in Table I-1 and were used to calculate potential
tolerances.

Data corrected for the combined residues of triflumizole and its
metabolites, determined as FA-1-1, in/on mustard greens were entered
into the tolerance spreadsheet.  Visual inspection of the lognormal
probability plot (Figure I-1) indicates that the dataset is reasonably
lognormal, and the results from the approximate Shapiro-Francia tests
(Figures I-2) confirm this assumption.  The calculated tolerance, using
residues corrected for declines of 0.15%/day during frozen storage, is
40 ppm for Brassica leafy greens.



Table I-1: Triflumizole Residues in/on Mustard Greens

Regulator:	EPA

Chemical:	Triflumizole

Crop:	Brassica-5B

PHI:	1 day

App. Rate:	.25 lb ai/A

Submitter:	IR-4

	Residues

	1.090

	1.490

	9.510

	15.960

	5.480

	5.570

	12.960

	7.010

	2.850

	3.730

	14.720

	20.270

	2.650

	4.710

	13.820

	11.520

	5.040

	4.400

	4.380

	7.200

Figure I-1.	Lognormal Probability Plot of Triflumizole Residues in/on
Mustard Greens.



Figure I-2.	Data Summary Sheet for Residues of Triflumizole in/on
Mustard Greens.  

Appendix II - International Tolerances

INTERNATIONAL RESIDUE LIMIT STATUS

Chemical Name:  1-(1-((4-chloro-2-(trifluoromethyl)
phenyl)imino)-2-propoxyethyl)-1H-imidazole

	Common Name: Triflumizole

	X Proposed tolerance

( Reevaluated tolerance

√ No Codex proposal step 6 or above

( No Codex proposal step 6 or above for the crops requested	Petition
Numbers: 7E7183

DP Number:  	341963

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nition:  Combined residues of triflumizole and its metabolites
containing the 4-chloro-2-trifluoromethylaniline moiety (FA-1-1),
calculated as parent

Crop (s)	MRL (mg/kg)	Crop(s) 	Tolerance (ppm)

Brassica, leafy greens, subgroup 5B	40

	Limits for Canada	Limits for Mexico

(Limits

√ No Limits for the crops requested	(No Limits

rop(s)	MRL (mg/kg)	Crop(s)	MRL (mg/kg)

	Notes/Special Instructions:  S.Funk, 11/16/2007.

Page   PAGE  1  of   NUMPAGES  18 

Triflumizole	Summary of Analytical Chemistry and Residue Data	DP Num:
341963