  SEQ CHAPTER \h \r 1 U. S. ENVIRONMENTAL PROTECTION AGENCY

Washington, D.C. 20460	

									            OFFICE OF

PREVENTION, PESTICIDES

AND TOXIC SUBSTANCES

								

Date: October 3, 2007 

MEMORANDUM 					

Subject:	Triflumizole Drinking Water Assessment in Support of New Use
Registration Action for Brassica, Leafy Greens, Subgroup 5B, Leafy
Greens Subgroup 4A (except Spinach), Papayas, and Hops.

	PC Code: 128879

	DP Barcode: 338654 and 344465	

To:		Pv Shah, Branch Chief, RAB 1

		Health Effects Division (7509P)

		Mary Waller, Product Manager, FB

Registration Division (7505P)

From:	Iwona L. Maher, Chemist, ERBI

		Thuy Nguyen, RAPL, ERB1

		Tom Bailey, Branch Chief, ERBI

Environmental Fate and Effects Division (7507P)

Attached is EFED’s Tier II drinking water assessment document in
support of triflumizole new use registration on brassica, leafy greens,
subgroup 5B, leafy greens subgroup 4A (except spinach), papayas, and
hops.  This assessment supplants any previous FQPA drinking water
assessments.

EXECUTIVE SUMMARY

Triflumizole is classified as a “reduce risk” chemical which acts as
a broad spectrum fungicide.  It is manufactured by Chemtura USA
Corporation under the registered pesticide product name Procure 480SC,
Procure 50WS, and Terragourd 50W.  Triflumizole is registered for
filberts, cherries, apples, pears, strawberries, cucurbits, and
ornamentals.  The risk assessment for uses on filberts was completed in
Feb. 2, 2006 (D312295) while the risk assessment for uses on cherries,
strawberries, cucurbits, and ornamentals was completed in May 21, 2001
(D242426).  Tier I drinking water assessment for triflumizole, including
degradates, was completed on March 3, 2002 (D281356) (S. Ramasamy, March
3, 2002).  Since then the registrant submitted an anaerobic aquatic
metabolism study.

Due to lack of comprehensive monitoring data, drinking water
concentration estimates were made by reliance on PRZM/EXAMS (surface
water) and SCI-GROW (ground water) modeling.

Among all the registered and proposed new uses, the highest estimated
drinking water concentrations (EDWCs) from surface water sources were
derived for aerial applications of trflumizole to cherries.  Up to date,
the maximum registered application rate for cherries is the highest
application rate allowed for triflumizole use hence it provides the
highest water concentrations.  The proposed Procure application rates
for brassica leafy greens subgroup 5B, leafy greens subgroup 4A (except
spinach), papayas, and hops are lower than those registered for cherries
hence this assessment is based on Procure application to cherries.  The
proposed application rates for brassica, leafy greens, subgroup 05B, and
leafy greens subgroup 4, papayas, and hops very from 0.125 to 0.375 lb
ai/acre for single application, and may not exceed 1.0 to 2.0 lbs
ai/acre per season (see Table 2).  The maximum single application rate
for cherries is 0.5 lb ai/acre with up to six applications made at the
minimum interval of 7 days between consecutive applications.  For aerial
applications, the acute drinking water concentration in surface water
(1-in-10 year annual peak concentration) reached a maximum of 37.4 μg/L
from use on cherries, the chronic non-cancer drinking water
concentration (1- in-10 year annual average concentration) is not
expected to exceed 15.8 μg/L and the cancer/chronic drinking water
concentration (30-year annual average) is not expected to exceed 12.0
μg/L from use on cherries.  For ground water, the SCI-GROW model
estimated the concentration of triflumizole in shallow ground 3.11 μg/L
from the use on cherries at the maximum application rate.  The estimated
drinking water concentrations represent the parent compound along with
the degradates containing the 4-chloro-2-trifluoromethyl aniline moiety
namely, FD-1-1, FM-6-1, FA-1-1, FM-5-1, FM-3-1, FD-2-1, and FM-8-1.  For
chemical name and structure refer to Appendix II.  

Table 1 presents the estimated drinking water concentrations for
triflumizole from aerial and ground applications on cherries.

Table 1.  Triflumizole Estimated Drinking Water Concentrations from
Surface Water Sources.

Drinking water source (model)	

Scenario	Estimated Drinking Water Concentrations (µg/L) 



1 in 10 year annual peak	1 in 10 year annual mean	36 year annual mean



Surface water

(PRZM/EXAMS) 	MI Cherries a

ground –  air blast 	

29.0			

12.1	

8.2

	MI Cherries a

aerial	

37.4 	

15.8	

12.0

Ground water

(SCI-GROW)	

MI Cherries	

3.11	

<3.11	

<3.11

a  – The default PCA (0.87) corrected values.

Submitted laboratory studies suggest that triflumizole dissipates with
half-lives (t½) ranging from 2 to 18 days, not likely to be persistent
under most environmental conditions (the field half-live less than 8
days) and, except for soils in a sand textural class with low organic
material, unlikely to be very mobile.  Triflumizole degradates may be
more persistent based on the longer half-lives (t½ (laboratory) = 8 to
142 days; t½ (field) = 102 and 133 days) for the combined residue
studies, thus, the total residues are considered moderately stable in
the environment.  The major degradate’s (FD-1-1) KOC values suggest
that it is more mobile than the parent compound, the KD and KOC values
range from 0.178-13.8 and 33.6-961.2, respectively.  

Triflumizole may drift off during application and runoff into the
surface water, but less likely reach ground water, unless under
vulnerable soils conditions it may have potential for leaching.
Triflumizole has some of the properties of a chemical with leaching
potential in vulnerable soils.  After application, total residues
(triflumizole and its degradates) may runoff into the adjacent surface
water and may potentially reach shallow ground water.

The fate and transport database for triflumizole is complete with the
exception of an aerobic aquatic metabolism study (162-4).  The missing
laboratory study would be beneficial in characterizing the potential for
triflumizole leaching to ground water or remaining in surface water at
concentrations of ecological or human health concern, and may be
requested for future risk assessments. A foliar dissipation study, in a
green house setting preferred, would be beneficial in characterizing the
half-life for modeling drinking water EECs via PRZM/EXAMS.  For future
risk assessment, a laboratory volatility study (163-3) for triflumizole
degradate
4-chloro-alpha-alpha-alpha-trifluoro-N-2-propoxyacetyl-o-toluidine
(FD-1-1) may be requested if FD-1-1 appears to be of human health
concern.  Majority of FD-1-1 volatilized during anaerobic aquatic
metabolism study.  The data requirement details are presented in
Appendix II of this document.

PROBLEM FORMULATION

This is a Tier II drinking water assessment (DWA) that uses modeling and
available monitoring data to estimate the groundwater and surface water
concentrations of pesticides in drinking water source water
(pre-treatment) resulting from pesticide use on sites that are
vulnerable.  

While Tier I DWAs are designed to screen out chemicals with low
potential risk for posing a drinking water concern, the Tier II
assessment provides more site-specific, refined modeling estimates of
pesticide exposure by using additional environmental fate parameters,
specific soil data, weather information, and management practices to
estimate daily concentrations of pesticides for an extended period of
time (up to 30 years).  This Tier II surface water assessment reflects
application of triflumizole at the maximum label rate to cherries and
with scenario intended to be representative of an environment that is
more vulnerable to runoff and leaching than most where cherries may be
grown.

2.2.	Background

common name:

chemical name:

IUPAC:	

Triflumizole

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

3-chloro-4-[(2RS,4RS;2RS,4SR)-4-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)-1
,3-dioxolan-2-yl]phenyl 4-chlorophenyl ether

CAS:
1-[2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-ylmeth
yl]-1H-1,2,4-triazole

Reg. No.:	119446-68-3

Formula:	C19H17Cl2N3O3

pesticide type:

chemical class:	Fungicides

 

Imidazole

 

InChI:

	InChI=1/C19H17Cl2N3O3/c1-13-9-25-19(27-13,10-24-12-22-11-23-24)17-7-6-1
6(8-18(17)21)26-15-4-2-14(20)3-5-15/h2-8,11-13H,9-10H2,1H3/t13?,19?





Triflumizole([1-[1-((4-chloro-2(trifluoromethyl)
phenyl)imino)-2-propoxyethyl]-1H-Imidazole]; 

CAS 68694-11-1) is an imidazole that is effective in inhibiting
ergosterol biosynthesis in fungi. Many fungi must synthesize ergosterol
which is a compound needed for the stabilization of membranes that make
up cell walls.  Target pests are powdery mildew, blossom blight, scab,
fruit rot, black and leaf spot.

2.3.	Use Characterization

  TC \l3 "		Overview of Pesticide Usage 

Triflumizole is a fungicide that is used as foliage, flower, nut spray,
and soil drench to control of fungus and blights on apples, cherries,
Christmas trees, conifer seed, filberts, cucurbits, grapes, ornamental
woody and herbaceous plants (flowering or non- flowering), pear,
pineapple and strawberries.  Triflumizole is formulated as a wettable
powder, soluble concentrate and liquid, and can be applied as various
spray treatments such as; ground, soil drench, aerial, microtube, high
and low volume ground sprayers, hand held wand, dipper, mist sprayer,
chemigation and sprinkler irrigation.  For formulation of Procure 480SC,
applications through any type of irrigation systems are not permitted. 

The currently approved triflumizole application rates for agricultural
uses range from 0.5 lb ai/acre (apples and cherries) to 0.1875 lb
ai/acre (filberts) for a single application (BEAD 2007) with a seasonal
maximum label rate of 3.0 lb ai/acre (cherries).  The proposed
application rate for Procure 480SC to control powdery mildew or black
spot in brassica leafy greens subgroup 5B, leafy greens subgroup 4A,
hops, and papayas very from 0.125 to 0.375 lb ai/acre for single
application, and may not exceed 1 to 2 lb ai/acre per season depending
on crop type.  A foliar spray to leafy vegetables can be made via ground
or aerial method.  Table 2 lists detailed application rates for those
proposed uses and the highest registered use rate.

Table 2.  Triflumizole application rates for the proposed and
registered1 uses.



Crop	Maximum application rate (lbs ai/A)	Maximum number of applications
per year2	Minimum interval between applications

	Single	Annual





Cherries1	

0.5	

3.0	

6	

7

Brassica Leafy Greens 5B	0.125-0.25	1.0	4	7-14

Leafy Greens 4A	0.125-0.25	1.0	4	7-14

Papayas	0.375	1.875	5	14

Hops	0.5	2.0	4	10

1 – It shows only the maximum registered application rate for
triflumizole registered uses.

2 – Calculated based on the max annual and single application rate
allowed per label.

The proposed Procure application rates for leafy greens (subgroup 5B and
4A), papayas, and hopes are lower than those registered for cherries
hence this assessment is based on Procure application to cherries.  The
maximum single application rate for cherries is 0.5 lb ai/acre with up
to six applications made at the minimum interval of 7 days between
consecutive applications.  

Conceptual Model

The source of the stressor considered is triflumizole fungicide (PC Code
128897) and triflumizole degradates containing the
4-chloro-2-trifluoromethyl aniline moiety.  During the HED MARC meeting
on February 26, 2002, the MARC committee has not excluded the possible
toxicological concern for the metabolites containing the
4-chloro-2-trifluoromethyl aniline moiety.  The half-lives for anaerobic
aquatic metabolism, aerobic soil metabolism, hydrolysis and photolysis
were calculated collectively for the parent and degradates of concern.
The estimated drinking water concentrations represent the degradates
containing the 4-chloro-2-trifluoromethyl aniline moiety namely, FD-1-1,
FM-6-1, FA-1-1, FM-5-1, FM-3-1, FD-2-1, and FM-8-1 along with the parent
compound.  

Triflumizole is not likely to be persistent under most environmental
conditions and, except for soils in a sand textural class with low
organic material, unlikely to be very mobile.  Triflumizole degradates
may be more persistent than the parent based on the longer half-lives
for the combined residue.  The half-lives derived for aquatic
photolysis, soil photolysis, aerobic soil metabolism, and aerobic
aquatic metabolism for total residues correspond to 12.7 days, 8 days,
44 days, and 142 days respectively.  The relatively high KOC values in
non-sand soils and the moderate adsorption characteristics in sandy
soils with organic carbon content greater than one percent suggest that
triflumizole has low potential to reach groundwater in most soils. 
However, triflumizole may present leaching potential in vulnerable
soils.  The KOC values for the degradate, FD-1-1, suggest that it is
more mobile than the parent compound.  Triflumizole total residues will
reach surface water in both the dissolved form and sorbed onto soils and
organic material for several weeks following application. 

Currently, triflumizole is applied via various spray treatments such as;
ground spray , soil drench, aerial, microtube, high and low volume
ground sprayers, hand held wand, dipper, chemigation, mist sprayer and
sprinkler irrigation.  The extent of acreage treated with triflumizole
is unknown, but the crops to be treated are collectively grown
throughout the United States.  

Drinking water contamination is the result of runoff and spray drift
from labeled applications, and the magnitude is largely dependent on the
use patterns and environmental fate and transport characteristics of the
pesticide. 

3.	ANALYSIS

3.1.	Environmental Fate and Transport Characterization

Active Ingredient

  TC \l3 "		Environmental Fate and Transport Characterization 

The major pathways of triflumizole degradation appear to be hydrolysis
under acidic and alkaline conditions (8.9 days at pH 5.0; 3.9 days at pH
9.0), photolysis (2-3 days), anaerobic aquatic metabolism (7.7 days in a
total water: sediment system), and to lesser extent aerobic soil
metabolism.  Triflumizole is not likely to be persistent under most
environmental conditions.  It is unlikely to be very mobile except for
soils in a sand textural class with low organic material.  Based on the
laboratory and field study findings it has potential to reach
groundwater under vulnerable soil conditions (sandy soils), and it will
reach surface water in both the dissolved form, and sorbed onto soils,
and organic material for several weeks following application.

Triflumizole is converted to several degradates containing the
4-chloro-2-trifluoromethyl aniline moiety during hydrolysis, photolysis
as well as during aerobic soil metabolism and anaerobic aquatic
metabolism.  During the HED MARC meeting on February 26, 2002, the MARC
committee has not excluded the possible toxicological concern for the
metabolites containing the 4-chloro-2-trifluoromethyl aniline moiety. 

Triflumizole photolyzed relatively rapidly under simulated sunlight
conditions in water buffered to pH 7 and on the surface of soil with
half-lives from 2 to 3 days. Triflumizole hydrolyzed in buffered water
with calculated half-lives of 8.9, 64.6 and 3.9 days at pH 5, 7 and 9,
respectively. The major degradate of hydrolysis was found to be
4-chloro-alpha-alpha-alpha-trifluoro-N-2-propoxyacetyl-o-toluidine
(FD-1-1).  No photolysis and hydrolysis data are available for
triflumizole degradates.

In a laboratory aerobic soil metabolism study, triflumizole degraded
with a half-life of 18 days.  The major soil metabolite was identified
as 2-trifluoromethyl-4-chloroaniline (FA-1-1) with minor metabolites
comprising of 4-chloro-2-trifluoromethyl-propoxyacetanilide and
N-[4-chloro-2-(trifluoromethyl)phenyl]imino-2-propoxyethyl amine.  In an
anaerobic aquatic metabolism study triflumizole degraded with half-life
of 7.7 days in a pond water-sandy loam sediment system to FA-1-1 and
N-[4-chloro-2-(trifluoromethyl)phenyl]-N-hydroxy-2-propoxyacetamide
(M-1) while majority of FA-1-1 appear to volatilize.  No soil metabolism
and aquatic metabolism data are available for triflumizole degradates.  

Laboratory soil mobility studies (batch equilibrium and column leaching)
indicate that triflumizole has slightly mobile to relatively immobile
characteristics depending upon the type of soil and organic matter
content.  The reported Freundlich KD values for sand, sandy loam, silt
loam, and clay soils were 1.5, 7.6-63.3, 25.4, and 79.4, respectively. 
The corresponding KOC values for sand, sandy loam, silt loam, and clay
soils were 289, 1286-1993, 4113, and 2812, respectively.  The low KD of
1.5 in the sandy soil (organic matter content <1%) suggests that
triflumizole is mobile under those conditions.  The batch equilibrium
studies on triflumizole degradate,
4-chloro-alpha-alpha-alpha-trifluoro-N-2-propoxyacetyl-o-toluidine
(FD-1-1) suggests that it is more mobile than the parent compound (KOC:
33.6-961.2 for the FD-1-1).  However, field studies conducted on sand
and sandy loam soils indicated that triflumizole and its metabolites did
not leach in soil depths below 12 inches.

Laboratory findings for triflumizole are in agreement with field
dissipation studies with regard to soil metabolism half-life (18 days)
and abiotic degradation rates at similar environmental conditions (pH
and photoperiod) in the laboratory.  In a series of previously reviewed
cropped and non-cropped terrestrial field dissipation studies (2 valid
and 2 invalid), triflumizole dissipated with half-lives of less than 8
days following soil and foliar applications at 0.5 lb ai/acre.  No
triflumizole or degradates were found below the 6- to 12-inch soil
layer.  The major degradate found in all studies was
N-[4-chloro-2-(trifluoromethyl)phenyl]imino-2-propoxyethylamine (FM-6-1)
at 0.21 ppm.  2-trifluoromethyl-4-chloroaniline (FA-1-1) and 
4-chloro-alpha-alpha-alpha-trifluoro-N-2-propoxyacetyl-o-toluidine
(FD-1-1) were identified at <0.02-0.08 ppm.  These studies indicate that
triflumizole rapidly dissipated under field conditions similar to normal
product use.

In other two bare ground terrestrial field dissipation studies
(California and North Carolina), triflumizole and triflumizole
degradates, FA-1-1, FD-1-1, and FM-6-1 were studied, and results were
reported as FA-1-1 total residues.  Trifumizole was applied 8 times at
7-day intervals at a rate of 0.25 lbs. a.i./acre.  Total residue
half-lives (expressed as FA-1-1 equivalents) were estimated to be 102
days in the California study and 133 days in the North Carolina study. 
Triflumizole residues were not seen below the 6- to 12-inch soil layer
and only at very low concentrations, equal to or slightly above the
level of detection (LOD) or 0.01 ppm.  Pan evaporation data were not
supplied.  Therefore, it is difficult to conclude that leaching below
the 6- to 12-inch soil layer is unlikely because the site water balance
may not have been conducive to promote leaching.  The analytical method
selected did not permit the determination of individual species, parent
and each degradate.  However, these data and the data from the previous
terrestrial field dissipation studies might suggest that triflumizole
dissipates rather quickly, but triflumizole degradates may be more
persistent based on the longer half-lives for the combined residue
studies. 

Triflumizole appears to accumulate in fish.  BCFs for edible, nonedible,
and whole fish were 107x, 758x, and 393x, respectively.     

 

	B.	Total Residues

The half-lives for anaerobic aquatic metabolism, aerobic soil
metabolism, hydrolysis and photolysis were calculated collectively for
the parent and the degradates of concern which are the metabolites
containing the 4-chloro-2-trifluoromethyl aniline moiety (Appendix II). 
The half-lives derived for aquatic photolysis, soil photolysis, aerobic
soil metabolism, and anaerobic aquatic metabolism for total residues
(parent and its degradates) correspond to 12.7 days, 8 days, 44 days,
and 142 days (in a total water: sediment system), respectively.  These
data suggest that triflumizole and triflumizole degradates are
moderately persistent in the environment.  The total residue levels
during hydrolysis at all pH conditions are very stable (half-life of
several months to years).  However, in the environment the microbial
degradation pathways might have a greater influence than the non-biotic
pathways and therefore, the total residues appear moderately stable in
the environment. 

The registrant submitted a mobility study for one of triflumizole
degradates, FD-1-1.  The degradate KOC values suggest that it is more
mobile than the parent compound.  The Freundlich KD and KOC values for
FD-1-1 range from 0.178-13.8 and 33.6-961.2, respectively.  As an input
parameter in PRZM/EXAM modeling an average KOC value for parent and the
degradate (FD-1-1) was used.  The lowest KOC value of all available KOC
(parent and FD-1-1) was used in SCI-GROW modeling.  A recently submitted
anaerobic aquatic metabolism study suggests that FA-1-1 may dissipate
though volatilization.  In this study, organic volatiles as extracted
from the PUF plugs were mainly made up of FA-1-1; i.e. 50.6% of the
applied at study termination (365 days after application). 

In this drinking water assessment, in modeling aquatic EECs, the PRZM/
EXAMS input parameters were calculated for a total residues
(triflumizole and its degradates).  Detailed information on how the
individual modeling input parameters were derived can be obtained from
the “Tier I Estimated Drinking Water Concentrations for Triflumizole
Including Degradates” memo (S. Ramasamy, March 3, 2002) (D281356).  

3.2.	Drinking Water Exposure Modeling

Estimated drinking water concentrations (EDWCs) were generated using
EFED’s standard suite of models.  The currently registered maximum use
pattern for cherries was modeled.

	A.	Surface Water Assessment

A Tier II drinking water assessment was performed using PRZM 3.12/EXAMS
2.98.04 modeling with index reservoir (IR) scenarios and percent cropped
area (PCA) adjustment factors.  The assessment was based on triflumizole
proposed agricultural uses on cherries that is the highest application
rate among all the registered and proposed uses.

Table 3 lists the input parameters used for the PRZM/EXAMS modeling. 
The EDWCs for triflumizole are listed in Tables 1.

TABLE 3.  PRZM/EXAMS Input parameters for triflumizole use on cherries. 

Model Parameter	Value	Source

Maximum application rate per event (product label) 	Cherries:

0.5 lb ai/A (0. 56 kg ai/ha)	EPA Product Label for Procure 480 SC

Maximum number of applications per year	6 - cherries	Product label as
above



Minimum interval between applications	7 days - cherries

	Product label as above

Method of application	air-blast 

aerial 	Product label as above

First application date (day-month)	10-05 

	Assumed based on crop profile and planting dates data from PRZM crop
scenarios

Application rate efficiency	0.99 ground

0.95 aerial	Guidance for Selecting Input Parameters in Modeling the
Environmental Fate and Transport of Pesticides; Feb 2, 2002

Spray drift fraction	0.063 ground air-blast

0.16 aerial spray	Guidance for Selecting Input Parameters in Modeling
the Environmental Fate and Transport of Pesticides; Feb 2, 2002

Percent Crop Area (PCA) factors	0.87	Default PCA was chosen.

Aerobic soil metabolism  t ½2	44.2 days	MRID 00149861

Anaerobic aquatic metabolism  t ½3 

	426 days	MRID 47136403

Aerobic aquatic metabolism  t½  	88.4 days

	Assumed 2 x aerobic soil metabolism half-life input value because the
compound is stable to hydrolysis and no aerobic aquatic metabolism data
are available. (Guidance for Selecting Input Parameters in Modeling the
Environmental Fate and Transport of Pesticides; Feb 2, 2002)

Soil partition coefficient (KOC)

	1229 L/kg	MRIDs:  40824601 and 40824602

(average Koc value for parent and its degradate (FD-1-1) was used)

Aqueous photolysis t ½4	12.7 days	MRID 40494405

Hydrolysis t ½5	2767 days	MRID 40494404

Molecular weight	345.7 g/mole	Assumed molecular weight of parent

Solubility (pH 7, 20oC)	125 mg/l	Assumed the parent solubility for
degradates

Vapor pressure at 20oC	1.4 x 10-6 mm Hg	Assumed vapor pressure of parent

Henry’s Law Constant at 20oC	4.94 x 10-8 atm m3/mol	Henry’s Law 
constant estimated based on chemical solubility and vapor pressure

1 - The registrant water solubility was multiplied by 10 according to
Guidance for Selecting Input Parameters in Modeling the Environmental
Fate and Transport of Pesticides; Feb 2, 2002

2 - 90% upper bound of available combined (parent and degradates) half
lives (half-lives (n= 5) = 44.3, 39.1, 17.3, 49, and 26.3 days) was
used.

3 – Only one half-life was available hence the input parameter was
assumed to be three times the half-life value as per Feb. 2002
guidelines.  The half-life was calculated for parent and degradates
(FA-1-1, FD-1-1, and M-1).

4 - Parameter calculated for parent and degradates.

5 - Used an average half-life calculated out of four combined half-lives
available for the parent and degradates, i.e. 5433, 2436, 680, 2520
days.

Cherry leaf spot (Blumeriella jaapii) is an important disease of
cherries in Michigan. It is a fungal disease of the foliage that can
adversely affect the vigor and health of trees. Only 5-6 hours of leaf
wetness during optimal temperatures are sufficient to cause a light
infection. Any infection is significant because of the ability of the
fungus to rapidly initiate secondary disease cycles resulting in
increased disease incidence and spread.  Small reddish to purplish
lesions first appear on the upper surface of leaves. The lesions turn
brown and yellow (chlorotic) and can coalesce. Chlorotic infected leaves
abscise, often resulting in severe defoliation.  Poorly controlled leaf
spot can cause early defoliation of trees, resulting in reduced winter
hardiness and even tree death.  Optimum conditions for disease
development are temperatures of 60 to 68 F with rainfall or high
humidity (minimum of 12 hours leaf wetness to initiate a moderate
infection).  The usual timing of the first fungicide application to
control leaf spot is at early bloom stage (popcorn stage), with
consecutive applications as needed up through petal fall.  Therefore,
for the modeling purpose, May 10, around bloom time, was selected for
the initial application date when the disease potentially may develop.

	B.	Ground Water Assessment

No ground water monitoring data were available for triflumizole. 
Triflumizole was not listed in the 1992 Pesticides in Ground Water
Database, U.S. EPA/EFED/EFGWB, and was not included in the National
Pesticide Survey, USEPA 1990.  Therefore, the SCI-GROW screening model
was used to estimate ground water concentrations.  The model estimates
upper-bound ground water concentrations of pesticides likely to occur
when the pesticide is used at the maximum allowable rate in areas where
ground water is vulnerable to contamination.  The modeling input
parameters were selected according to EFED’s Guidance for Selecting
Input Parameters in Modeling the Environmental Fate and Transport of
Pesticides, Feb 2, 2002.  Table 4 lists the modeling input parameters.

Table 4.  SCI-GROW input parameters for Triflumizole applied on cherries
at the maximum label application rate.

MODEL INPUT VARIABLE	INPUT VALUES	SOURCE

Application Rate	0.5 lbs/A	Procure 50 WS Label

Number of Applications / Season	6	 Procure 50 WS Label

Aerobic Soil Metabolism half-life1	39.1 days 	MRID 00149861

Koc2	33.6 L/kg	MRID 40824601

1 There were five values, which is more than four, thus, the median of
all five values calculated for total residues was used (i.e. 44.3, 39.1,
17.3, 49, 26.3).

2 Koc values for parent and its degradate, FD-1-1, show greater than
three-folds variations (Koc ranged from 33.6 to 4114), therefore, the
lowest value (for FD-1-1) was used as per Feb. 28, 2002 guidance.

The SCI-GROW model estimated triflumizole concentration in drinking
water from shallow ground water sources to be 3.11µg/L from the maximum
application rate.  This concentration can be considered as both the
acute and chronic value.  The modeling output file is provided in
Appendix III of this document.

3.3.	Monitoring Data 

Comprehensive monitoring data for triflumizole in surface water and
ground water are not available.  Currently, there are no
chemical-specific federal or state drinking/ground water standards for
triflumizole.  

3.4.	Drinking Water Treatment

No data were located regarding the fate of triflumizole during the
drinking water treatment process.  It should be noted, however, that the
agricultural waste water treatment technique, that used TiO2 catalyst
particles and a high-pressure water current may result in triflumizole
removal of up to 80 percent of the initial concentrations.  This
procedure was examined by Japanese researchers
(http://sciencelinks.jp/j-east/article/200703/000020070307A0003791.php).

EXPOSURE CHARACTERIZATION

μg/L and 3.11 μg/L for groundwater.  For surface water chronic and
cancer EDWCs are 15.8 μg/L and 12.0 μg/L, respectively.

The following uncertainties have been identified in the environmental
fate properties and exposure models for triflumizole:  

•	The microbial degradation on foliage was assumed stable for the
modeling purposes due to lack of statistically sound foliar dissipation
studies.  The registrant submitted magnitude of residues studies on
mustard greens can not be used for a calculation of foliar dissipation
half-life.  

•	The wash-off of the foliage was considered using the default
wash-off coefficient assumption of 0.5 cm-1.  

•	Spray drift was directly considered in the assessments as a route of
loading to the reservoir, with higher levels of spray drift for aerial
applications than ground spray applications.

•	The aerobic soil metabolism half-life input parameter was calculated
for the parent and degradates.  The submitted laboratory studies,
however, suggest that one of degradates is potentially volatile. 
Volatilization may be the major route of dissipation for this degradate.


•	The only submitted soil adsorption/desorption studies for
triflumizole and its degradate, FD-1-1, were conducted on the soils that
were autoclaved prior to use, which may have affected their
adsorptive/desorptive properties.  Therefore, the observed data on
mobility of triflumizole and its major metabolite FD-1-1 in the soils of
the two submitted studies may not be accurate (MRIDs:  40824601 and
40824602).  Autoclaving has been shown to affect the physical as well as
biological properties of soils; specifically, autoclaving has been shown
to reduce the adsorptive properties of same soils.  Triflumizole and
FD-1-1 may therefore be less mobile than those studies indicate.

•	This MI cherry scenario was adjusted with the default PCA of 0.87. 
In general, the likelihood that multiple crops from the list of proposed
uses will be found within single watersheds where triflumizole is used
is unknown; therefore, specific PCA adjustment factor was not used.  The
potential to underestimate or overestimate environmental concentrations
may be associated with the application of the default (0.87) PCA factor
for this use.  

APPENDIX I.

Table 1. Environmental Fate and Transport Data Submitted for
Triflumizole



Study Guideline	

Data Requirement	Study Classification	Is Data Requirement Satisfied	MRID

161-1	Hydrolysis	 Acceptable	Yes	40494404

161-2	Aquatic Photodegradation	 Acceptable	Yes	40494405

161-3	Soil Photodegradation	 Acceptable	Yes	(00156550

40638302)

162-1	Aerobic Soil Metabolism	 Acceptable	Yes	00149861

162-2	Anaerobic Soil Metabolism	No study



162-3	Anaerobic Aquatic Metabolism

	47136403

162-4	Anaerobic Soil Metabolism	No study



163-1	Leaching/Adsorption/

Desorption	 Acceptable	Yes	(40602601

41256601

41256602

41706602

40824601

40824602)

164-1	Soil Dissipation

Field Dissipation	 Acceptable

Acceptable	Yes

Yes	(00156551

40494406)

45262700

44971304

44971305

164-2	Aquatic Dissipation	No study



165-4

	Fish Accumulation

	 Acceptable	Yes	(00149865

40494407)



Appendix II:  Table 1.  Chemical name and structure of triflumizole and
its degradates of potential concern

Common Name/Number	Chemical Structure

Triflumizole

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

 

Metabolite FA-1-1

4-chloro-2-trifluoromethylaniline moiety

 

Metabolite FM-5-1



Metabolite FM-6-1

 

Metabolite FM-8-1

 

Metabolite FD-2-1

 

Metabolite FD-1-1

 

Metabolite M-1





APPENDIX III

I.	PRZM/EXAM Output Files

Michigan Cherry Scenario – ground air blast application 

stored as triflumMicherriesIRAb_10-05.out

Chemical: triflumizole

PRZM environment: MICherriesSTD.txt	modified Tueday, 29 May 2007 at
12:56:56

EXAMS environment: ir298.exv	modified Thuday, 29 August 2002 at 15:34:12

Metfile: w14850.dvf	modified Wedday, 3 July 2002 at 09:05:40

Water segment concentrations (ppb)

Year	Peak	96 hr	21 Day	60 Day	90 Day	Yearly

1961	8.646	8.38	7.62	6.574	5.979	2.934

1962	20.54	19.97	17.96	14.74	13.19	7.478

1963	14.08	13.77	13.28	12.43	11.54	7.854

1964	14.7	14.32	12.95	11.33	10.43	7.478

1965	10.75	10.53	10.05	9.241	8.742	7.346

1966	10.07	9.819	9.228	8.298	7.897	6.434

1967	12.05	11.78	10.79	9.397	8.701	6.286

1968	10.38	10.17	9.225	8.741	8.243	5.863

1969	37.25	36.23	34.03	29.41	26.43	13.42

1970	14.98	14.69	14.12	13.28	12.68	11.8

1971	11.99	11.71	11.11	10.22	9.668	8.258

1972	16.13	15.68	14.82	12.7	11.75	8.38

1973	12.09	11.83	11.04	10.36	9.727	7.506

1974	19.2	18.7	17.64	15.44	13.97	8.542

1975	15.09	14.76	13.79	11.93	10.93	8.476

1976	10.96	10.71	10.11	9.165	8.587	7.054

1977	10.9	10.64	10.04	8.658	8.201	6.275

1978	12.34	12.04	11.12	9.978	9.351	7.126

1979	14.29	13.96	12.74	11.02	11.1	8.096

1980	15.44	15.08	13.73	11.67	10.7	7.666

1981	23.39	22.76	20.95	17.84	16.67	10.2

1982	24.86	24.3	21.85	18.1	16.34	11.55

1983	16.88	16.46	15.01	14.59	13.97	11.31

1984	13.87	13.57	12.69	11.57	10.84	9.151

1985	20.89	20.32	18.27	16.63	15.75	10.14

1986	50.24	49.26	46.22	38.93	35.11	19.96

1987	27.62	26.99	24.77	22.15	21.18	18.29

1988	15.56	15.26	14.74	14.24	13.87	11.59

1989	33.9	33.04	29.85	24.42	22.12	13.06

1990	27.67	26.97	25.59	21.72	19.95	13.91

Sorted results

Prob.	Peak	96 hr	21 Day	60 Day	90 Day	Yearly

0.032258064516129	50.24	49.26	46.22	38.93	35.11	19.96

0.0645161290322581	37.25	36.23	34.03	29.41	26.43	18.29

0.0967741935483871	33.9	33.04	29.85	24.42	22.12	13.91

0.129032258064516	27.67	26.99	25.59	22.15	21.18	13.42

0.161290322580645	27.62	26.97	24.77	21.72	19.95	13.06

0.193548387096774	24.86	24.3	21.85	18.1	16.67	11.8

0.225806451612903	23.39	22.76	20.95	17.84	16.34	11.59

0.258064516129032	20.89	20.32	18.27	16.63	15.75	11.55

0.290322580645161	20.54	19.97	17.96	15.44	13.97	11.31

0.32258064516129	19.2	18.7	17.64	14.74	13.97	10.2

0.354838709677419	16.88	16.46	15.01	14.59	13.87	10.14

0.387096774193548	16.13	15.68	14.82	14.24	13.19	9.151

0.419354838709677	15.56	15.26	14.74	13.28	12.68	8.542

0.451612903225806	15.44	15.08	14.12	12.7	11.75	8.476

0.483870967741936	15.09	14.76	13.79	12.43	11.54	8.38

0.516129032258065	14.98	14.69	13.73	11.93	11.1	8.258

0.548387096774194	14.7	14.32	13.28	11.67	10.93	8.096

0.580645161290323	14.29	13.96	12.95	11.57	10.84	7.854

0.612903225806452	14.08	13.77	12.74	11.33	10.7	7.666

0.645161290322581	13.87	13.57	12.69	11.02	10.43	7.506

0.67741935483871	12.34	12.04	11.12	10.36	9.727	7.478

0.709677419354839	12.09	11.83	11.11	10.22	9.668	7.478

0.741935483870968	12.05	11.78	11.04	9.978	9.351	7.346

0.774193548387097	11.99	11.71	10.79	9.397	8.742	7.126

0.806451612903226	10.96	10.71	10.11	9.241	8.701	7.054

0.838709677419355	10.9	10.64	10.05	9.165	8.587	6.434

0.870967741935484	10.75	10.53	10.04	8.741	8.243	6.286

0.903225806451613	10.38	10.17	9.228	8.658	8.201	6.275

0.935483870967742	10.07	9.819	9.225	8.298	7.897	5.863

0.967741935483871	8.646	8.38	7.62	6.574	5.979	2.934

0.1	33.277	32.435	29.424	24.193	22.026	13.861

					Average of yearly averages:	9.44776666666667

Inputs generated by pe5.pl - Novemeber 2006

Data used for this run:

Output File: triflumMicherriesIRAb_10-05

Metfile:	w14850.dvf

PRZM scenario:	MICherriesSTD.txt

EXAMS environment file:	ir298.exv

Chemical Name:	triflumizole

Description	Variable Name	Value	Units	Comments

Molecular weight	mwt	345.7	g/mol

Henry's Law Const.	henry	4.94e-8	atm-m^3/mol

Vapor Pressure	vapr	1.4e-6	torr

Solubility	sol	125	mg/L

Kd	Kd		mg/L

Koc	Koc	1229	mg/L

Photolysis half-life	kdp	12.7	days	Half-life

Aerobic Aquatic Metabolism	kbacw	88.4	days	Halfife

Anaerobic Aquatic Metabolism	kbacs	426	days	Halfife

Aerobic Soil Metabolism	asm	44.2	days	Halfife

Hydrolysis:	pH 7	2767	days	Half-life

Method:	CAM	2	integer	See PRZM manual

Incorporation Depth:	DEPI	0	cm

Application Rate:	TAPP	0.56	kg/ha

Application Efficiency:	APPEFF	0.99	fraction

Spray Drift	DRFT	.063	fraction of application rate applied to pond

Application Date	Date	10-05	dd/mm or dd/mmm or dd-mm or dd-mmm

Interval 1	interval	7	days	Set to 0 or delete line for single app.

app. rate 1	apprate		kg/ha

Interval 2	interval	7	days	Set to 0 or delete line for single app.

app. rate 2	apprate		kg/ha

Interval 3	interval	7	days	Set to 0 or delete line for single app.

app. rate 3	apprate		kg/ha

Interval 4	interval	7	days	Set to 0 or delete line for single app.

app. rate 4	apprate		kg/ha

Interval 5	interval	7	days	Set to 0 or delete line for single app.

app. rate 5	apprate		kg/ha

Record 17:	FILTRA	

	IPSCND	1

	UPTKF	

Record 18:	PLVKRT	

	PLDKRT	

	FEXTRC	0.5

Flag for Index Res. Run	IR	Reservoir

Flag for runoff calc.	RUNOFF	total	none, monthly or total(average of
entire run)

Michigan Cherry Scenario – aerial application 

stored as triflumMicherriesIRair_10-05.out

Chemical: triflumizole

PRZM environment: MICherriesSTD.txt	modified Tueday, 29 May 2007 at
12:56:56

EXAMS environment: ir298.exv	modified Thuday, 29 August 2002 at 15:34:12

Metfile: w14850.dvf	modified Wedday, 3 July 2002 at 09:05:40

Water segment concentrations (ppb)

Year	Peak	96 hr	21 Day	60 Day	90 Day	Yearly

1961	14.82	14.32	12.89	10.85	9.756	5.352

1962	29.69	28.84	25.98	21.28	19.25	11.16

1963	24.81	24.18	22.68	20.4	18.77	12.1

1964	21.82	21.27	19.29	18.15	17.46	11.92

1965	21.72	21.17	20.02	17.96	16.59	12.03

1966	21.38	20.8	19.32	17	15.71	11.12

1967	22.9	22.47	20.64	18.08	16.54	11.02

1968	20.55	19.99	18.9	17.32	16.04	10.57

1969	45.76	44.55	41.45	36.61	32.7	17.77

1970	25.93	25.31	23.81	21.63	20.04	16.12

1971	22.95	22.34	20.84	18.58	17.18	12.65

1972	23.29	22.68	21.2	19.68	18.87	12.86

1973	22.34	21.75	20.33	18.87	17.39	12.01

1974	29.99	29.17	27.16	23.29	21.04	12.98

1975	22.81	22.21	20.73	18.29	16.64	12.89

1976	22	21.41	19.93	17.64	16.18	11.56

1977	21.98	21.41	19.94	17.23	15.77	10.87

1978	23.46	22.84	21.06	18.6	17.11	11.75

1979	23.57	22.99	21.66	19.27	18.53	12.8

1980	25.83	25.2	23.07	20.24	18.52	12.39

1981	33.95	33.02	30.08	25.15	23.24	14.74

1982	31.44	30.81	27.83	23.31	22.43	16.05

1983	24.61	24.01	23.02	22.07	21.27	15.76

1984	24.28	23.69	22.52	20.14	18.56	13.67

1985	27.08	26.39	23.92	21.53	20.29	14.66

1986	57.96	56.9	53.83	45.05	40.53	24.08

1987	31.89	31.21	28.81	26.76	26.86	22.32

1988	26.32	25.69	24.18	22.02	20.56	15.78

1989	43.74	42.6	38.4	31.92	29	17.3

1990	36.11	35.2	33.58	28.63	26.44	18.19

Sorted results

Prob.	Peak	96 hr	21 Day	60 Day	90 Day	Yearly

0.032258064516129	57.96	56.9	53.83	45.05	40.53	24.08

0.0645161290322581	45.76	44.55	41.45	36.61	32.7	22.32

0.0967741935483871	43.74	42.6	38.4	31.92	29	18.19

0.129032258064516	36.11	35.2	33.58	28.63	26.86	17.77

0.161290322580645	33.95	33.02	30.08	26.76	26.44	17.3

0.193548387096774	31.89	31.21	28.81	25.15	23.24	16.12

0.225806451612903	31.44	30.81	27.83	23.31	22.43	16.05

0.258064516129032	29.99	29.17	27.16	23.29	21.27	15.78

0.290322580645161	29.69	28.84	25.98	22.07	21.04	15.76

0.32258064516129	27.08	26.39	24.18	22.02	20.56	14.74

0.354838709677419	26.32	25.69	23.92	21.63	20.29	14.66

0.387096774193548	25.93	25.31	23.81	21.53	20.04	13.67

0.419354838709677	25.83	25.2	23.07	21.28	19.25	12.98

0.451612903225806	24.81	24.18	23.02	20.4	18.87	12.89

0.483870967741936	24.61	24.01	22.68	20.24	18.77	12.86

0.516129032258065	24.28	23.69	22.52	20.14	18.56	12.8

0.548387096774194	23.57	22.99	21.66	19.68	18.53	12.65

0.580645161290323	23.46	22.84	21.2	19.27	18.52	12.39

0.612903225806452	23.29	22.68	21.06	18.87	17.46	12.1

0.645161290322581	22.95	22.47	20.84	18.6	17.39	12.03

0.67741935483871	22.9	22.34	20.73	18.58	17.18	12.01

0.709677419354839	22.81	22.21	20.64	18.29	17.11	11.92

0.741935483870968	22.34	21.75	20.33	18.15	16.64	11.75

0.774193548387097	22	21.41	20.02	18.08	16.59	11.56

0.806451612903226	21.98	21.41	19.94	17.96	16.54	11.16

0.838709677419355	21.82	21.27	19.93	17.64	16.18	11.12

0.870967741935484	21.72	21.17	19.32	17.32	16.04	11.02

0.903225806451613	21.38	20.8	19.29	17.23	15.77	10.87

0.935483870967742	20.55	19.99	18.9	17	15.71	10.57

0.967741935483871	14.82	14.32	12.89	10.85	9.756	5.352

0.1	42.977	41.86	37.918	31.591	28.786	18.148

					Average of yearly averages:	13.8157333333333

Inputs generated by pe5.pl - Novemeber 2006

Data used for this run:

Output File: triflumMicherriesIRair_10-05

Metfile:	w14850.dvf

PRZM scenario:	MICherriesSTD.txt

EXAMS environment file:	ir298.exv

Chemical Name:	triflumizole

Description	Variable Name	Value	Units	Comments

Molecular weight	mwt	345.7	g/mol

Henry's Law Const.	henry	4.94e-8	atm-m^3/mol

Vapor Pressure	vapr	1.4e-6	torr

Solubility	sol	125	mg/L

Kd	Kd		mg/L

Koc	Koc	1229	mg/L

Photolysis half-life	kdp	12.7	days	Half-life

Aerobic Aquatic Metabolism	kbacw	88.4	days	Halfife

Anaerobic Aquatic Metabolism	kbacs	426	days	Halfife

Aerobic Soil Metabolism	asm	44.2	days	Halfife

Hydrolysis:	pH 7	2767	days	Half-life

Method:	CAM	2	integer	See PRZM manual

Incorporation Depth:	DEPI	0	cm

Application Rate:	TAPP	0.56	kg/ha

Application Efficiency:	APPEFF	0.95	fraction

Spray Drift	DRFT	.16	fraction of application rate applied to pond

Application Date	Date	10-05	dd/mm or dd/mmm or dd-mm or dd-mmm

Interval 1	interval	7	days	Set to 0 or delete line for single app.

app. rate 1	apprate		kg/ha

Interval 2	interval	7	days	Set to 0 or delete line for single app.

app. rate 2	apprate		kg/ha

Interval 3	interval	7	days	Set to 0 or delete line for single app.

app. rate 3	apprate		kg/ha

Interval 4	interval	7	days	Set to 0 or delete line for single app.

app. rate 4	apprate		kg/ha

Interval 5	interval	7	days	Set to 0 or delete line for single app.

app. rate 5	apprate		kg/ha

Record 17:	FILTRA	

	IPSCND	1

	UPTKF	

Record 18:	PLVKRT	

	PLDKRT	

	FEXTRC	0.5

Flag for Index Res. Run	IR	Reservoir

Flag for runoff calc.	RUNOFF	total	none, monthly or total(average of
entire run)

II.	SCI-GROW Output Files

                           

                           SCIGROW

                          VERSION 2.3

            ENVIRONMENTAL FATE AND EFFECTS DIVISION

                 OFFICE OF PESTICIDE PROGRAMS

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 SciGrow version 2.3

 chemical:triflumizole 2

 time is  9/25/2007  17: 2: 7

 -----------------------------------------------------------------------
-

  Application      Number of       Total Use    Koc      Soil Aerobic

  rate (lb/acre)  applications   (lb/acre/yr)  (ml/g)   metabolism
(days)

 -----------------------------------------------------------------------
-

      0.500           6.0           3.000      3.36E+01       39.1

 -----------------------------------------------------------------------
-

 groundwater screening cond (ppb) =   3.11E+00 

 ***********************************************************************
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഍ግ䅐䕇†㈔ക഍഍഍

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