UNITED STATES ENVIRONMENTAL PROTECTION AGENCY 

WASHINGTON, D.C. 20460 

OFFICE OF CHEMICAL SAFETY AND 

POLLUTION PREVENTION 

MEMORANDUM 

Date: 

Subject: 

29-0CT-2013 

Triflumizole. Section 3 Registration for Greenhouse Uses on Tomato and 

Cucumber; Translations of Apple and Pear to Pome Fruit Group 11 - 1 0, Grape to 

Crop Subgroup 13-07F, and Strawberry to Crop Subgroup 13-07G, Except 

Cranberry. Summary of Analytical Chemistry and Residue Data. 

PC Code: 128879 DP Barcode: 0 413698 

Decision No.: 472282 Registration No.: NA 

Petition No.: 2E8119 Regulatory Action: Section 3 Registration 

Risk Assessment Type: NA Case No.: NA 

TXR No.: NA CAS No.: 68694-11-1 

MRID Nos.: 48998101 &48998102 40CFR: §180.476 

FROM: 

THROUGH: 

TO: 

WilliamH.Donovan,Ph.D.,Chemist LAJ~ cyj" 

Risk Assessment Branch (RAB) V 

Health Effects Division (7509P) 

Peter Savoia, Chemist ~J L. ()~~~ Michael S. Metzger, Branch Chie( ~ _)! ·- RAB VNII . 

Health Effects Division (7509P) 

Andrew Ertman!Barbara Madden, RM 05 

Risk Integration, Minor Use, Emergency Response Branch 

Registration Division (7505P) 

And 

Seyed Tadayon, Risk Assessor 

Risk Assessment Branch (RAB) V 

Health Effects Division (7509P) 

Page I of 18 
Triflumizole Summary of Analytical Chemistry and Residue Data 0413698 

1.0 Executive Summary 

The Interregional Research Project Number 4 (IR-4) has submitted a petition for establishing 

tolerances for triflumizole in or on greenhouse grown cucumber and tomato, and for converting 

the established tolerances for apple and pear to the same tolerance level for pome fruit crop 

group 11-10, for converting the established tolerance for grape to the same tolerance level for 

crop subgroup 13-07F, and for converting the established tolerance for strawberry to the same 

tolerance level for crop subgroup 13-070, except cranberry. 

Adequate residue chemistry data have been provided to support the new use requests for 

triflumizole. The nature of the residue in plants is adequately understood for the purposes of this 

petition based on previously reviewed plant metabolism studies. Field trials are of adequate 

number and geographic representation. Crop field trial data analyses employed validated 

analytical methods that determine the residue of concern via common moiety, and are supported 

by adequate storage stability data. An adequate analytical enforcement method is available to 

enforce triflumizole tolerances. In a stability study conducted concurrently with the cucumber 

magnitude of the residue study, combined triflumizole residues declined on average by 38% in 

cucumber samples stored at -20°C for 832 days, or 0.0457% per day. Based on this factor, 

corrections were made to the cucumber field trial data to account for residue decline in frozen 

storage. Tolerance recommendations were based on use of the Organization for Economic 

Cooperation and Development (OECD) Maximum Residue Limit (MRL) calculation procedures, 

international harmonization considerations, and data translation where appropriate. No 

processing studies were required to support the proposed use patterns. 

Previously reviewed confined and field rotational crop studies support the rotational crop 

restrictions specified on current labels. The proposed label for greenhouse grown cucumber and 

tomato should be revised to omit the rotational crop restriction since greenhouse soils are not 

typically reused. 

2.0 Regulatory Recommendations 

Pending submission of a revised Section Bas detailed in Section 2.3, there are no residue 

chemistry considerations that would preclude establishment of the recommended tolerances. 

2.1 Data Deficiencies/Data Needs 

There are no residue chemistry deficiencies identified for this petition. 

2.2 Tolerance Considerations 

2.2.1 Enforcement Analytical Method 

An adequate GC/NPD method is available (Method I in PAM Vol. II) 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 F A-1-1 coupled with distillation of FA-1-1 into hexane. 

Page 2 of 18 
Triflumizole Summary of Analytical Chemistry and Residue Data 0413698 

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 oftriflumizole. The 

method LOQ is 0.5 ppm for plant commodities. 

2.2.2 Recommended Tolerances 

The proposed tolerances and commodity definitions are appropriate and match HED 

recommendations. Table 2.2.2 summarizes triflumizole tolerances resulting from the current 

petition. 

Table 2.2.2. Tolerance Summary for Triflumizole'. 

Commodity Proposed Recommended Comments; Correct Commodify 

Tolerance (ppm) Tolerance (ppm) Definilion 

Tomato 1.5 1.5 Greenhouse tomatoes only. 

Fruit, pome, group Il-l 0 0.5 0.50 

Fruit, small, vine climbing, 

except fuzzy kiwifruit, 2.5 2.5 

subgroup 13-0?F 

Berry, low growing, 

subgroup 13-0?G, except 2.0 2.0 

cranberry 

Includes established field uses for 

Vegetable, cucurbit, group 9 0.502 0.50 cucurbits and the proposed 

greenhouse use on cucumber. 

These tolerances should be established under 40 CFR § 180.476. 2 The established and proposed tolerances for crop group 9 are identical and cover the proposed use on greenhouse 

grown cucumber. 

Note to RD: Upon establishment of the recommended tolerances listed above, tolerance listings 

for the following individual crops should be revoked since they will be included in the new crop 

group and crop subgroups listings: apple, pear, grape, and strawberry. 

In addition, some recommendations for changes made in a previous review are not currently 

reflected in the 40 CFR § 180.476 (0346779, W. Cutchin, 10/1/08). The following tolerances 

should be deleted from 180.476(a)(l): apple, dry pomace; apple, wet pomace; grape, dried 

pomace; grape, raisin, waste; and grape, wet pomace. The commodity listed as "cilantro, leaves" 

should be changed to "coriander, leaves.'' Also, the following tolerances should be deleted from 

l80.476(a)(2): cattle, meat; egg; goat, meat; hog, fat; hog, meat; hog, meat byproducts; horse, 

meat; milk; poultry, fat; poultry, meat; poultry, meat byproducts; and sheep, meat. Tolerance 

levels for the following commodities should be lowered from 0.5 to 0.10 ppm: fat of cattle, 

sheep, goat, and horse. Tolerance levels for the following commodities should be lowered from 

0.5 to 0.20 ppm: meat byproducts of cattle, sheep, goat, and horse. 

2.2.3 Revisions to Petitioned-For Tolerances 

None 

2.2.4 International Harmonization 

Page 3 of 18 
Tritlumizole Summary of Analytical Chemistry and Residue Data 0413698 

Codex has not established Maximum Residue Limits (MRLs) for residues oftriflumizole inion 

raw agricultural or processed commodities. Tolerance definitions are harmonized between 

Canada and the U.S. Additionally, all Canadian MRLs are harmonized with the corresponding 

US tolerance levels (see Appendix A). Triflumizole is not registered for use in Canada. The 

Canadian MRLs for triflumizole were set to support the import oftreated commodities. 

2.3 Label Recommendations 

HED recommends that the rotational crop restriction be omitted from the greenhouse grown 

cucumber and tomato use directions since soils in greenhouses are not typically reused. 

3.0 Introduction 

3.1 Chemical Identity 

Table 3.1 Triflumizole and Metabolite Nomenclature 

Chemical structure FC 

~N r~b-CI N~-\_ 0 

\ 

CH2CH2CH3 

Empirical formula C1sH1sN30CIF3 

Common name Tritlumizole 

IUPAC1 name (E)-4-chloro-a,a,a-tritluoro-N-( I-im idazol-1-yl-2-propoxyethyl idene )-otoluidine 

CAS2 name 1-[(IE)-1-[[ 4-chloro-2-(tritluoromethyl)phenyl]imino )-2-propoxyethyi]-1Himidazole 

CAS registry number 68694- 11-1 

End-use products (EPs) Procurellll SOWS; EPA Reg. No. 400-431 

Procure® 480SC; EPA Reg. No. 400-518 

Metabolite structure F3C 

~ N=( ~ 0 

~ 

Cl 

~ Common Name FM-6- 1 

IUPAC name N-(4-Chloro-2-tritluoromethyl-phenyl)-2-propoxy-acetamidine 

Page 4 of 18 
Triflumizole Summary of Analytical Chemistry and Residue Data 0413698 

Table 3.1 Triflumizole and Metabolite Nomenclature 

Chemical class Imidazole 

Common moiety structure F3C H,N_:oCI 

Common name F A-l-1 

IUPAC name 4-chloro-2-tri fluoromethy Ian il ine 

Livestock metabolite CF3 CI-Q-NH2 

OH 

Common name FA-1-5 

IUPAC name 4-chloro-2-hydroxy-6-trifluoromethylaniline 

Livestock metabolite 

CF3 CI-Q-NH2 

S03H 

OH 

Common name FA-1-5-S 

IUPAC name 4-ch loro-2-hydroxy-6-trifluoromethy Janil ine sui fate 

1 TUPAC = International Union of Pure and Applied Chemistry 2 CAS = Chemical Abstracts Service 

3.2 PhysicaUChemical Characteristics 

Physiochemical properties for triflumizole are shown in Table 3 .2. 

TABLE 3.2. Physicochemical Properties of Triflumizole 

Parameter Value Reference 

Melting point/range 63 .5 oc DEB# 6410, J. Smith, 117/92 

pH N/A 

Bulk Density (at 20 °C) 0.50 - 0.70 

Water solubility (g/L at 20 °C) 0.0125 (at pH 5.9) 

Solvent solubility (g/1 00 mL at 20 <>q Chloroform 222 

Acetone 144 

n-Hexane 1.76 

Methanol 49.6 

Xylene 63 .9 

Vapor pressure (25 °C) 1.4 x 10·

6 mmHg 

Dissociation constant (pK. at 25 ·q 3.7 

Octanol/water partition coefficient Kow at 25 25 

oc 

UV /visible absorption spectrum Amax = 204, 230, and 308 nm (acidic) D368710, P. Savoia, 09-

Amax = 204, 236, and 300 nm (neutral) NOV-2009 

Amax = 232 and 292 nm (basic) 

Page 5 of 18 
Triflumizole Summary of Analytical Chemistry and Residue Data 0413698 

3.3 Pesticide Use Pattern/Directions for Use (860.1200) 

Table 3.3. Summary of Directions for Proposed Uses of Triflumizole. 

Applic. Timing; Formulation Applic. Max. No. Max. Seasonal PHI Type: and [EPA Reg. Rate Applic. per Applic. Rate (days) Use Directions and Limitations 

Equip. No.] (lb ai/A) Season (lb ai/A) 

Pome fruit crop group ll-10 

Broadcast fo liar; 4 lb/gal FIC 0.5 4 2.0 14 A minimum RTI of I 0 days is 

At first indication [400 -518] specified. Apply in a 

of disease; minimum of SO gallA for 

Ground or aerial ground applications. 

equipment 

Sma ll fruit vine climbing, except fu zzy kiwifruit, crop subgroup 13-07F 

Low-growing berry crop subgroup 13-07G, except cran berry 

Broadcast fo liar; 

4 lb/gal FIC 0.25 4 1.0 14 A minimum RTI of2 1 days is 

[400-5 18] specified. Apply in a At first indication minimum of 50 gal/A for of disease; 

ground applications. Ground and Aerial 

(aerial application for grape is equipment 

prohibited) 

Greenhouse grown vegetable (Cucumber a nd Tomato) 

Manually and 4 lb/gal SC 0.25 s 1.25 0 Do not plant leafy or non-leafy 

mechanically [400-521] Brassica vegetables or fru iting 

pressurized hand vegetables within 30 days afier 

gun sprayer application. Do not plant bulb 

vegetables or root vegetables 

within 60 days after 

application. Do no plant 

cotton, small cereal grains and 

all other crops not registered on 

the label within one year after 

application. 

REI: 12 hours. 

Minimum RTI: 7 days. 

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

uses. The proposed maximum application rates, RTis, and PHis are supported by the submitted 

field trial data. Because greenhouse soils are not reused, there is no need for a rotational crop 

restriction for greenhouse grown vegetables. HED recommends removal of the proposed 

rotational crop restriction for greenhouse cucumber and tomato. 

4.0 Metabolite/Degradate Residue Profile 

4.1 Nature of the Residue 

4.1.1 Summary of Plant Metabolism (860.1300) 

The nature of the residue in plants is adequately understood for purposes of the crops that are the 

subject of this petition. 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-trifluoromethylaniline moiety, 

Page6of l8 
Triflumizole Summary of Analytical Chemistry and Residue Data D413698 

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). 

4.1.2 Summary of Livestock Metabolism (860.1300) 

There are no livestock feedstuffs associated with the proposed uses. Therefore, data 

requirements for livestock metabolism are not relevant to this tolerance petition. 

4.1.3 Summary of Confined Rotational Crops (860.1850) 

D341963, J.R. Tomerlin, 07-DEC-2007 

Adequate confined field rotational crop studies were submitted in conjunction with a tolerance 

petition for use oftriflumizole on strawberries (PP# 1F06297, D274589, J. Tyler, 3111/02; 

D327173, J. Tyler, 10/19/06). Based on the results ofthe confined study, the MARC (meeting 

2/26/02) concluded that the residues of concern in rotational crops include triflumizole and all 

metabolites containing the 4-chloro-2-trifluoromethylaniline moiety for purposes of risk 

assessment and the tolerance expression. 

4.2 Residues of Concern Summary and Rationale 

The Metabolism Assessment Review Committee (MARC) determined that residues of concern 

should include parent triflumizole and all metabolites containing the 4-chloro-2-

trifluoromethylaniline moiety (D280869, J. Tyler, 3/13/02). Metabolites containing the 4-chloro2-trifluoromethylaniline moiety are unlikely to be less toxic than the parent compound. As they 

were found to comprise > 10% TRR in the plant metabolism studies, it is appropriate to include 

these compounds in the risk assessment. Further, it is also appropriate to include these 

metabolites in the tolerance expression since a common moiety enforcement method is available. 

Table 4.2 Summary of Metabolites and Degradates to be included in the Risk 

Assessment and Tolerance Expression 

Matrix Residues included in Risk Assessment Residues included in Tolerance Expression 

Plants (Primary and Triflumizole and all metabolites Triflumizole and all metabolites containing 

containing the 4-chloro-2- the 4-chloro-2-trifluoromethylani line Rotational Crops) trifluoromethylan iline moiety moiety 

Triflumizole, 4-chloro-2- Tritlumizole, 4-chloro-2-

Livestock trifluoromethylaniline sulfate, and other trifluoromethylaniline sulfate, and other 

metabolites containing the 4-chloro-2- metabolites containing the 4-chloro-2-

trifluoromethylaniline moiety trifluoromethylaniline moiety 

Triflumizole and all metabolites 

Drinking Water containing the 4-chloro-2- Not Applicable 

trifluoromethylaniline moiety 

Page 7 of 18 
Triflumizole Summary of Analytical Chemistry and Residue Data 0413698 

5.0 Residue Profile 

5.1 Residue Analytical Methods (860.1340) 

5.1.1 Data Collection Methods 

Samples from the current cucumber and tomato 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 (D274589, J. Tyler, 3111/02). 

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) 175 and 195 ions for quantitation. Residues are 

expressed in parent equivalents by multiplying the amount ofF A-1-1 by a molecular weight 

conversion factor of 1.77. The lowest limit of method validation (LLMV) was 0.1 and 0.5 ppm 

for the cucumber and tomato trials, respectively. 

Based on acceptable concurrent method recovery data, the analytical method is adequate for data 

collection. 

5.1.2 Multi-Residue Methods (860.1360) 

Data are available on the recovery oftriflumizole through FDA Multiresidue Method Testing 

Protocols. The FDA PESTDA T A database dated 06/2005 (PAM Vol. I, Appendix I), indicates 

that triflumizole is completely recovered using Multiresidue Method Section 302 (Protocol D) 

without cleanup. Information was not listed for Methods 303 and 304. 

5.1.3 Tolerance Enforcement Methods 

An adequate GC/NPD method is available (Method I in PAM Vol. II) for determining the 

combined residues of triflumizole and its metabolites containing the F A-1-1 moiety in plant 

commodities (G. Kramer, 12/16/94). This common moiety method involves alkaline hydrolysis 

of parent and its metabolites to F A-1-1 coupled with distillation ofF A-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 oftriflumizole. The 

method LOQ is 0.5 ppm for plant commodities. 

Page 8 of 18 
Triflumizole Summary of Analytical Chemistry and Residue Data 0413698 

5.1.4 Submittal of Analytical Reference Standards (860.1650) 

Analytical standards for triflumizole (CAS # 1 08-62-3) and its regulated metabolites are 

available at the EPA National Pesticide Standards Repository [personal communication from T. 

Cole of ACB/BEAD to S. Tadayon, 08/20/2013] with the following receipt and expiration dates: 

Inventory 

Chemical Name Notes Company Date Reed Date Exp 

triflumizole Chemtura 8/16/2013 1/31/2018 

triflumizole metabolite FA-1-1 Chemtura 5/9/2011 9/30/2015 

triflumizole metabolit e FA-1-5 Chemtura 5/9/2011 8/31/2015 

triflumizole metabolite FA-1-5 sulfate Chemtura 9/ 14/2010 8/31/2015 

triflumizole metabolite FM-6-1 Chemtura 9/10/2010 5/31/2014 

Prior to the listed expiration dates, fresh standards should be re-submitted to the Repository. The 

reference standard(s) should be sent to the Analytical Chemistry Lab, which is located at Fort 

Meade, to the attention of Theresa Cole at the following address: 

USEPA 

National Pesticide Standards Repository/Analytical Chemistry Branch/OPP 

701 Mapes Road 

Fort George G. Meade, MD 20755-5350 

The full 9 digit zip code is mandatory or the mail will be returned. 

5.2 Storage Stability (860.1380) 

Adequate storage stability data are available indicating that triflumizole is stable under frozen 

storage conditions for at least 12 months in apples, grapes, and cherries (PP#6F3372, S. Malak, 

1125/90; and 0242429, J. Tyler, 3111/02), 10 months in cucurbit vegetables and strawberries 

(0271003, J. Tyler, 3111/02; and 0 274589, J. Tyler, 3/11/02), and 3.2 months in filberts 

(0312293, J. Tyler, 5118/05). However, significant residue decline in frozen storage has also 

been observed in the following matrices: mustard greens (44% decline in 9.5 months] 

(D338653, J. Tomerlin, 07-DEC-2007), broccoli [58% decline in 7.6 months], and cabbage (50% 

decline in 8 months] (0346779, W. Cutchin, 01-0CT-2008). When residue decline in the 

storage stability study exceeds 30%, corrections to the magnitude of the residue data are needed 

to avoid underestimating residue and tolerance levels. 

Storage stability studies were conducted in conjunction with the submitted cucumber and tomato 

field trials. For these studies, control samples of cucumber and tomato were fortified separately 

with triflumizole and its metabolites> FM-6-1 and F A- 1-1, each at 0.5 ppm, and stored under the 

same conditions (-20°C) as the field trial samples. At the end of the analytical phase, the stored 

Page 9 of 18 
Triflumizole Summary of Analytical Chemistry and Residue Data 0413698 

samples were analyzed in triplicate along with a control sample and samples freshly fortified 

with each analyte. Acceptable residue stability was observed over the 552 day storage interval in 

the tomato storage stability as residue decline was assessed to be 12%. 

In contrast, the cucumber storage stability study showed significant decline. Thus, the average 

recovery from the stored samples (corrected for concurrent recoveries) was 69%, 77% and 39% 

for parent, FM-6-1, and F A-1- 1, respectively; for a mean average corrected recovery of 62% for 

all three analytes. These recoveries correlate to declines of 31%, 23%, and 61% [average of 

38%] over 832 days of storage and indicate a potential for residue decline in frozen cucumber. 

Because the method converts parent and all metabolites to a common moiety, corrections for the 

individual residues could not be determined. Therefore, the average decline of 38% over 832 

days (0.0457%/day decrease) was used to correct residue values according to the equation Rc = 

Ru -:- (1 - (0.000457 x DAYS)), where Rc is the corrected residue concentration, Ru is the 

uncorrected residue concentration, and DAYS is the number of days in storage. 

In the submitted cucumber field trials, samples were held in storage at -20°C for 517-881 days 

(:S29 months) prior to extraction for analysis. Corrected residues were calculated using the 

actual storage interval for each sample and a decline factor of0.0457%/day. 

Conclusions. The available storage stability data are adequate. Although earlier studies 

indicated that triflumizole is stable under frozen storage in cucurbit vegetables for at least 10 

months, the cucumber samples in the greenhouse trials were stored for significantly longer 

periods of time. The storage stability data submitted in support of the greenhouse cucumber 

trials indicate that residues decline on average by 0.0457% per day; therefore, to properly assess 

triflumizole residue levels in the cucumber magnitude of the residue studies, reported residue 

levels were corrected for decline during frozen storage. 

5.3 Residue Data 

5.3.1 Crop Field Trials (860.1500) 

4899810 l.der (Cucumber Greenhouse Trials) 

489981 02.der (Tomato Greenhouse Trials) 

Cucumber Greenhouse Trials 

The Interregional Research Project No.4 (IR-4) submitted magnitude of the residue data for 

triflumizole on greenhouse cucumber. Four greenhouse trials were conducted in the United 

· States in EPA Region 2: Salisbury, Maryland (1 trial), Region 3: Citra, Florida (1 trial), Region 

6: Weslaco, Texas (1 trial) and Region 9: Fort Collins, Colorado (1 trial). 

The trials reflect the use offive foliar directed applications of triflumizole, at a rate of 0.25 lb 

ai/ A, a 7 -day retreatment interval (R TI), and a 0-day pre-harvest interval (PHI), without the use 

of a surfactant. At the Colorado greenhouse site, a decline trial was conducted with the last 

application 0, 3, 7, 12 and 15 days before harvest (0-15 day PHI). 

Samples were stored frozen for up to 881 days 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 832 days of frozen (-20°C) storage by 31%, 23% and 

Page 10 of 18 
Triflumizole Summary of Analytical Chemistry and Residue Data 0413698 

61%, respectively (38% averaged decline). As the analytical method converts parent and all 

metabolites to a common moiety, an average decline of 0.0457% per day (38%/832) was used to 

correct residue values according to the equation Rc = Ru + (1 - (0.000457 x DAYS)), where Rc 

is the conected residue concentration, Ru is the uncorrected 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 0.045 ppm, and 

the calculated LOD was 0.015 ppm. The LLMV was 0.1 ppm. 

Following five broadcast foliar applications of triflumizole totaling 1.25 lb ai/ A, the combined 

residues (uncorrected for storage declines) were <0.1 0 - 0.27 ppm in/on 8 samples of cucumber 

harvested at a 0-day PHI, and with a 7-day RTI. The average uncorrected residue was 0.17 ppm 

and the highest average field trial (HAFT) residue was 0.26 ppm. When corrected for potential 

declines during storage, combined residues in/on all 8 samples were <0.14 - 0.39 ppm, the 

average residue was 0.25 ppm, and the HAFT residue was 0.34 ppm. In the decline study, total 

triflumizole residues were at or below the LLMV at all sampling intervals; thus, no decline trend 

could be discerned. The results from these studies are summarized in Table 5.3.1.1. 

TABLE 5.3.1.1 Summary of Residue Data from Greenhouse Cucumber Field Trials with Triflumizole 

Total Applic. PHI Residue Levels 

Commodity Rate (ppm) 

(lb ai/A) (days) n' I Min. I Max. I HAFT I Median I Mean I Std. Dev. 

Uncorrected Results 

Greenhouse I. 150-1.292 0 8 I <o. 1o 1 0.27 I 0.26 I 0.14 I 0. 17 I 0.09 

Cucumber Corrected Results 

I. 150-1.292 0 8 I <0.14 I 0.39 I 0.34 I 0.22 I 0.25 I 0.10 

Number of samples- 2 x numbe1 of field tnals. 

Conclusions: The number of cucumber greenhouse trials and their geographical distribution are 

adequate (four trials were recommended in an EPA/HED ChemSAC decision of September 17, 

2008). The storage stability study indicated that residues declined during frozen storage at an 

average rate of0.0457% per day. The corrected cucumber data set was analyzed using the 

OECD MRL calculation procedures, which determined a tolerance level of 0.8 ppm for 

greenhouse grown cucumber is appropriate (see Appendix B). However, HED concludes that 

the established tolerance of 0.5 ppm for cucurbit vegetables group 9 is adequate to cover 

greenhouse cucumber for the following reasons: 1) the greenhouse cucumber HAFT is 0.34 ppm 

(less than the established crop group 9 tolerance), and 2) keeping the established crop group 9 

tolerance at 0.5 ppm retains harmonization with the PMRA MRL. 

Tomato Greenhouse Trials 

IR-4 submitted field trial data for triflumizole on greenhouse tomato. Four greenhouse trials 

were conducted in the United States in EPA region 2: Salisbury, Maryland (I trial), region 5: 

Arlington, Wisconsin (1 trial), region 6: Weslaco, Texas (1 trial), and region 10: Parlier, 

California ( 1 trial). 

The trials reflect the use of four foliar directed applications of triflumizole, at a rate of 0.25 lb 

Page 11 of 18 
Triflumizole Summary of Analytical Chemistry and Residue Data D413698 

ai/A, a 7-day retreatment interval (RTI), and a 0-day pre-harvest interval (PHI), without the use 

of a surfactant. This protocol was followed except at the Texas site where five applications of 

the test substance were made at 6-14 day intervals and 0-day PHI. At the California greenhouse 

site a decline trial was conducted with the last application 0, 1, 4, 8, 10, and 15 days before 

harvest (0-15 day PHI). 

Samples were stored frozen for up to 556 days 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 552 days offrozen (-20°C) storage by 17%,2% and 

16%, respectively. Thus, triflumizole residues were stable inion frozen tomato over the 

maximum storage interval in the magnitude of the residue studies. 

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 0.23 ppm, and the 

calculated LOD was 0.077 ppm. The LLMV was 0.5 ppm. 

Following four broadcast foliar applications of 4 lb ai/gal SC triflumizole totaling 1.0 lb ai/ A, the 

combined residues were <0.50 - 0.88 ppm inion 8 samples of tomato harvested at a 0-day PHI. 

The average residue was 0.59 ppm and the HAFT residue was 0.76 ppm. Triflumizole residues 

above the LLMV of 0.5 ppm were found in both trials that used small tomato varieties, while 

residues were below the LLMV in both trials that used large tomato varieties. In the decline 

study, total triflumizole residues were below the LLMV at all sampling intervals; thus, no 

decline trend could be discerned. The results from these studies are summarized in Table 

5.3.1.2. 

TABLE 5.3.1.2. Summary of Residue Data from Greenhouse Tomato Field Trials with Triflumizole 

Total Applic. PHI 

Residue Levels 

Commodity Rate (days) (ppm) 

(lb ai/A) n' Min. Max. HAFT Median Mean Std. Dev. 

Greenhouse 0.921-1.284 0 8 <0.50 0.88 0.76 0.50 0.59 0. 14 Tomato 

Number of - samples - 2 x number of field t11als. 

Conclusions: The number of tomato greenhouse trials and their geographical distribution are 

adequate (four trials were recommended in an EPA/l-IED ChemSAC decision ofNovember 16, 

2005). Although three of the four tomato trials involved the use of just four applications of 

triflumizole at a rate of0.25 lb ai/A (for a seasonal rate of 1.0 lb ai/A) rather than the label 

maximum of 5 treatments at 0.25 lb ai/ A (for a seasonal rate of 1.25 lb ai/ A), HED concludes 

that the results are acceptable since three of the four trials reflect use of 80% of the maximum 

seasonal rate, and one trial matches the maximum seasonal rate. The results suggest that tomato 

size may be an important factor for triflumizole residues in this crop, with higher residues likely 

in small tomato varieties. The tomato data set was analyzed using the OECD MRL calculation 

procedures to determine the recommended tolerance level of 1.5 ppm for greenhouse grown 

tomato (see Appendix B). 

Tolerance Conversions to Crop Groups/Subgroups 

Page 12 of 18 
Triflumizole Summary of Analytical Chemistry and Residue Data 0413698 

• Apple and Pear to Pome Fruit Group 11-10 

IR-4 proposed that the established tolerances of 0.5 ppm for apple and pear be converted to pome 

fruit group 11-10, also at 0.5 ppm. This request is supported by the following observations: 1) 

apple and pear are the representative commodities of the pome fruit crop group, 2) the 

triflumizole use pattern is identical for apple and pear (and for the proposed crop group use), 3) 

apple and pear have identical tolerance levels, and 4) proposed revisions to the Procure® 480SC 

label, submitted as part of Section B of the petition, are consistent with the requested conversion. 

• Grape to Crop Subgroup 13-07F [Fruit, small vine climbing, except fuzzy kiwifruit, 

subgroup 13 -07F] 

IR-4 proposed that the established tolerance of2.5 ppm for grape be converted to crop subgroup 

13-07F, also at 2.5 ppm. This request is supported by extension of the grape use pattern to 

include crop subgroup 13-07F, as indicated in the proposed revisions to the Procure® 480SC 

label, submitted as part of Section B of the petition. Grape is the representative commodity for 

crop subgroup 13-07F. 

• Strawberry to Crop Subgroup 13-07G, Except Cranberry [Berry, low growing, subgroup 

13-07F, except cranberry] 

IR-4 proposed that the established tolerance of2.0 ppm for strawberry be converted to crop 

subgroup 13-07G, except cranberry, also at 2.0 ppm. This request is supported by extension of 

the strawberry use pattern to include crop subgroup 13-07G, except cranberry, as indicated in the 

proposed revisions to the Procure® 480SC label, submitted as part of Section B of the petition. 

Strawberry is the representative commodity for crop subgroup 13-07G. 

Conclusions: HED concludes that the tolerance conversions proposed by IR-4 are acceptable. 

Upon establishment of the requested crop group/subgroup tolerances, the individual crop 

tolerances for apple, pear, grape, and strawberry should be revoked as they will be included in 

the group/subgroup tolerance listings. 

5.3.2 Field Rotational Crops (860.1900) 

0341963, J.R. Tomerlin, 07-DEC-2007 

Adequate limited field rotational crop studies were submitted in conjunction with a tolerance 

petition for use oftriflumizole on strawberries (PP#1F06297, 0274589, J. Tyler, 3111/02; 

0 327173, J. Tyler, 1 0/19/06). Results from the limited rotational crop field trials indicated that 

the following plant-back intervals (PBis) 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 current labels include 

rotational crop restrictions that are consistent with the above PBis; the proposed label directions 

for greenhouse grown cucumber and tomato do not need to include rotational crop restrictions 

since soils in greenhouses are not typically reused (email message from B. Schneider toW. 

Donovan, 16-SEP-2013, and from B. Barney (IR-4) to A. Ertman, 24-SEP-2013). 

Page 13 of 18 
Triflumizole Summary of Analytical Chemistry and Residue Data 0413698 

5.3.3 Processed Food and Feed {860.1520) 

There are no processed commodities associated with greenhouse cucumber or tomato. Although 

greenhouse tomatoes could potentially be processed, economic considerations limit this 

possibility (email message from B. Schneider toW. Donovan, 01-AUG-2013). Therefore, data 

requirements for processed food and feed are not relevant to this tolerance petition. 

5.3.4 Meat, Milk, Poultry and Eggs (860.1480) 

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. 

5.4 Food Residue Profile 

Adequate residue chemistry data have been provided for triflumizole. Field trials are of adequate 

number and geographic representation. Data analyses employed validated analytical methods 

and are supported by adequate storage stability data. Residues oftriflumizole demonstrated 

satisfactory stability in frozen storage except for fortified samples of cucumber, where residues 

declined 38% over 832 days. Accordingly, magnitude of the residue data for cucumber was 

corrected for degradation during frozen storage. No tomato processing studies were submitted 

because triflumizole use is limited to greenhouse-grown tomato varieties, and these are not 

expected to be processed for economic reasons. 

To reiterate conclusions from previous triflumizole reviews (D346779, W. Cutchin, 1 011/08), 

the following tolerances should be deleted from 180.476(a)(l ): apple, dry pomace; apple, wet 

pomace; grape, dried pomace; grape, raisin, waste; and grape, wet pomace. The commodity 

listed as "cilantro, leaves" should be changed to "coriander, leaves." Also, the following 

tolerances should be deleted from 180.476(a)(2): cattle, meat; egg; goat, meat; hog, fat; hog, 

meat; hog, meat byproducts; horse, meat; milk; poultry, fat; poultry, meat; poultry, meat 

byproducts; and sheep, meat. Tolerance levels for the following commodities should be lowered 

from 0.5 to 0.10 ppm: fat of cattle, sheep, goat, and horse. Tolerance levels for the following 

commodities should be lowered from 0.5 to 0.20 ppm: meat byproducts of cattle, sheep, goat, 

and horse. 

The following PBis are appropriate for rotated crops: 30 days for spinach 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. 

6.0 Tolerance Derivations 

The recommended tolerances for trif1urnizole were derived by 1) use of the OECD MRL 

calculation procedures for tomato, and 2) direct translation for crop group 10-11, and crop 

subgroups 13-07F and 13-07G. The computed tolerance level for greenhouse grown cucumber 

was 0.80 ppm, based on OECD MRL calculation procedures. However, HED concludes that the 

established tolerance of 0.5 ppm for cucurbit vegetables group 9 is adequate to cover greenhouse 

Page 14 of 18 
Triflumizole Summary of Analytical Chemistry and Residue Data D413698 

cucumber for the following reasons: 1) the greenhouse cucumber HAFT is 0.34 ppm (less than 

the established crop group 9 tolerance), and 2) keeping the established crop group 9 tolerance at 

0.5 ppm retains harmonization with the PMRA MRL. 

List of Appendices 

A. International Residue Limits Table. 

B. Tolerance Calculations. 

Attachments 

4899810 1.der.docx 

489981 02.der.docx 

Page 15 of 18 
Triflumizole Summary of Analytical Chemistry and Residue Data 0413698 

Appendix A. International Residue Limits Table 

Triflumizole (128879; 09112/2013) 

Summa1y of US and International Tolerances and Maximum Residue Limits 

Residue Definition: 

us Canada Mexicol Codex 

40 CFR 40 CFR § 180.476 1-[ 1-[[ 4-chloro-2- None 

Plants: parent compound tritlumizole, 1-( 1-((4- (trifluoromethyl)phenyl] imino ]-2-

ch loro-2-(trifluoromethy l)phenyl)imino )-2- propoxyethyl]-1 H-imidazole, 

propoxyethyl)-1 H -imidazole, and its including metabolites 

metabolites containing the 4-chloro-2- containing the 4-chloro-2-

trifluoromethylaniline moiety, calculated as trifluoromethylaniline moiety, 

stoichiometric equivalent of the parent expressed as triflumizole 

compound. 

Commodity1 Tolerance (ppm) /Maximum Residue Limit (mglkg) 

us Canada Mexico2 Codex 

Tomato 1.5 

Fruit, pome, group Il-l 0 0.50 0.5 apples, pears 

Fruit, small, vine climbing, except 2.5 2.5 grapes 

fuzzy kiwifruit, subgroup 13-07F 

Berry, low growing, subgroup 13- 2.0 2 strawberries 

07G, except cranberry 

0.5 balsam apples, balsam pears, 

cantaloupes, chayote fruit, Chinese 

cucumbers, Chinese waxgourds, citron 

Vegetable, cucurbit, group 9 0.50 melons, cucumbers, edible gourds, 

muskmelons (other than those listed in 

this item) pumpkins, summer squash. 

watermelons, west Indian gherkins, 

winter squash 

Completed: M. Negussie; 09/ 13/13 

1 Includes only commodities of interest for this action. Tolerance values should be the HED recommendations and 

not those proposed by the applicant. 

2 Mexico adopts US tolerances and/or Codex MRLs for its export purposes. 

Page 16 of 18 
Appendix B. Results of OECD Tolerance Calculations 

Triflumizole 

GH Cucwnber 

USA 

5 x 0.25 lb ai/A, 0 day PHI 

Total number of data {n) 

Percentage of censored data 

Nwnber of non-censored data 

Lowest residue 

Highest residue 

Median residue 

Mean 

Standard deviation {SD) 

Correction factor for censoring {CF) 

Proposed MRL estimate 

- Highest residue 

- Mean + 4 SD 

- CF x 3 Mean 

Unrounded MRL 

Rounded MRL 

High uncertainty of MRL e s t imate . 

[Small dataset] 

Residues {mg/kg) N 

0.14 1 

0.18 1 

0.3 3 1 

0. 34 1 

Page 17 of 18 

4 

0% 

4 

0 . 140 

0.340 

0.255 

0 . 248 

0.102 

1 .000 

0 .34 0 

0 .6 57 

0 . 743 

0 . 743 

0 . 8 
Triflumizole Summary of Analytical Chemistry and Residue Data 

Triflurnizole 

GH Tomato 

USA 

4 x 0 . 25 lb a i/A, 0 day PHI 

Total number of data (n) 

Percentage of censored data 

Number of non-censored data 

Lowest residue 

Highest residue 

Median residue 

Mean 

Standard deviation (SD) 

Correction factor for censoring (CF) 

Proposed MRL estimate 

- Highest residue 

- Mean + 4 SD 

- CF x 3 Mean 

Unrounded MRL 

Rounded MRL 

High uncer tainty of MRL estimate. 

[Small dataset ] 

Residues (mg/kg) n 

< 0.5 2 

0.585 1 

0.755 1 

Page 18 of 18 

4 

50% 

2 

0.500 

0.755 

0.543 

0.585 

0.120 

0 . 667 

0 . 755 

1 . 066 

1.170 

1.170 

1.5 

0413698 
.. . ~ Triflumizole/128879 I CHEMTURA /400 

10•• DACO 7.4.117.4.2/0PPTS 860.1500/0ECD llA 6.3.1, 6.3.2, 6.3.3 and IliA 8.3.1; 8.3,2, 8.3.3 

Crop Field Trial- Greenhouse Tomato 

Primary Evaluator 

Peer Reviewer 

Approved by 

STUDY REPORTS: 

California Department of Pesticide Regulation 

Theresa Ratto, Ph.D., StaffEnvironmental Scientist, 

California Department of Pesticide Regulation 

William H. Donovan, Ph.D., Senior Chemist 

Risk Assessment Branch V, Health Effects Division 

Environmental Protection Agency (EPA) 

Date: 

/2 -ky -'J.o/3 

Date: 

,~;N4--~/3 

Date: 

i ·;)-AU&- ~013 

MRID No. 489981-02, Barney, W. (2012) Triflumizole: Magnitude of the Residue on Tomato 

(Greenhouse), Final Report. Study No. 268265. Unpublished study prepared by William 

Barney, IR-4 Project, 154 pages. 

EXECUTIVE SUMMARY: 

The Interregional Research Project No.4 (IR-4) has submitted field trial data for triftumizole on 

greenhouse tomato. Four greenhouse trials were conducted in the United States in EPA region 2: 

Salisbury, Maryland (I trial), region 5: Arlington, Wisconsin (I trial), region 6: Weslaco, Texas 

(I trial), and region I 0: Parlier, California (I trial) during the growing season 2010. The number 

and geographical distribution of the supervised field trials on greenhouse tomato are adequate. 

At each test location, experimental plants were treated with foliar directed applications of 

triflumizole, the active ingredient ( 42.14%) in Procure® 480SC. The studies targeted four 

applications a rate of0.25 lb ai/A, a 7-day retreatment interval (RTI), and a 0-day pre-harvest 

interval (PHI), with the use of a non-ionic surfactant. This protocol was followed except at the 

Texas site where five applications of the test substance were made at 6-14 day intervals and 0· 

day PHI. At the California greenhouse site a decline trial was conducted with the last application 

0, I, 4, 8, I 0, and 15 days before harvest (0- 15 day PHI). 

Samples of greenhouse tomato were analyzed using the method derived from "Determination of 

Tritlumizole in Crops," Analytical Method #Meth-115, Revision #3, Morse laboratories, Inc., 

July 18, 2003. The study followed IR-4 National Pesticide Clearance Laboratory Phase Protocol 

PR# 09299 as amended. Modifications made did not negatively affect the performance of the 

method. Residues of triflumizole and its an.iline-containing metabolites were converted to F A-ll (4-chloro-2-trifluoromethylaniline) by acidic and alkaline reflux, followed by distillation. The 

DP Barcode 04 I 3698 f MRID No. 489981-02 Page I of 10 
Triflumizole/ 128879 I CHEMTURA /400 

DACO 7.4.117.4.2/0PPTS 860.1500/0ECD IIA 6.3. 1, 6.3.2, 6.3.3 and 111A 8.3. 1, 8.3.2, 8.3.3 

Crop Field Trial - Greenhouse Tomato 

distillate was acidified and then extracted with ethyl acetate. If necessary, further clean-up was 

achieved by concentrating the ethyl acetate layers and using an optional silica solid phase 

extraction (SPE) procedure. Total triflumizole residues were quantitated using a gas 

chromatograph (GC) equipped with a mass selective detector (MSD) in selective ion monitoring 

(SIM) mode. All residues were converted to F A-1-1 and expressed in parent equivalents. 

The method was validated at 0.5, 1.0, and 10.0 ppm for triflumizole, FM-6-1 {(IE) N'-[4-chloro2-(trifluoromethyl)phenyl)-2-propoxyethanimidamide}, and F A-1-1 in greenhouse tomato 

samples. Average recoveries of triflumizole, FM-6-1, and FA-1-1 were 89 ± 10% (n = 9), 86 ± 

10% (n = 9), and 91 ± 5% (n = 9), respectively. The calculated limit of detection (LOD) and 

limit of quantitation (LOQ) for F A-1-1 on greenhouse tomato were 0.077 ppm and 0.229 ppm, 

respectively. The lowest level of method validation (LLMV) was 0.50 ppm. 

A freezer storage stability study was conducted in conjunction with this study. The maximum 

storage interval for greenhouse tomato samples during the study was 556 days. Average 

recoveries from storage stability greenhouse tomato samples fortified at 1.0 ppm and stored for 

552 days under the same conditions as field trials samples, were 68 ± 11% (n = 3), 80 ± 10% (n 

= 3), and 75 ± 2% (n = 3) for triflumizole, FM-6-l , and FA-1-1 , respectively. Because the 

storage stability study demonstrated adequate residue stability, no corrections to the magnitude 

of the residue data were needed. 

The field trials support the use of triflumizole in/on greenhouse tomato according to the 

following use pattern: up to four broadcast foliar applications at 0.25 lb ai/A per application 

[maximum of 1.0 lb ai/A per season], a 7-day RTI, and a 0-day PHI. Triflumizole residues in 

greenhouse tomatoes were 0.88 ppm or less when an SC formulation was applied according to 

the supported use pattern, and residues in small tomato varieties were found to be higher than in 

large tomato varieties. In the decline study, residues of total triflumizole were <0.50 ppm from 

day 0 to day 15; thus, no residue decline trend was discernible. 

STUDY/WAIVER ACCEPTABILITY/DEFICIENCIES/CLARIFICATIONS: 

Under the conditions and parameters used in the study, the field trial residue data are classified 

as scientifically acceptable. 

The acceptability of this study for regulatory purposes is addressed in the forthcoming U.S. EPA 

Residue Chemistry Summary Document [DP Barcode D413698]. 

COMPLIANCE: 

Signed and dated Good Laboratory Practice (GLP), Quality Assurance and Data Confidentiality 

Statements were provided. 

This study meets current GLP Requirements of 40 CFR Part 160 except the following deviations, 

which do not affect the conclusions presented in this report. 

DP Barcode 0413698 I MRID No. 489981-02 Page 2 of 10 
Tritlumizole/ 128879 / CHEMTURA /400 

DACO 7.4.117.4.2/0PPTS 860.1 500/0ECD IIA 6.3.1, 6.3.2, 6.3.3 and III A 8.3.1, 8.3.2, 8.3.3 

Crop Field Trial - Greenhouse Tomato 

1. At all field trials, supporting data such as soil characterization, weather, irrigation, 

cultural practices, site history records, and maintenance chemical applications were not 

collected in strict adherence to 40 CFR 160 guidelines. 

2. At all field trials, the scales used to roughly estimate the weight of the samples at the field 

trial site were not calibrated or maintained under GLP. 

A. BACKGROUND INFORMATION 

The active ingredient, triflumizole: (N-[4-chloro-2-(trifluoromethyl) phenyi)-N-[1-(l Himidazole- 1-yl)-2-propoxyethylidene] amine), used in this study is an imidazole that is effective 

in inhibiting ergosterol biosynthesis in fungi. The ergosterol is needed for the stabilization of 

membranes that make up cell walls in fungi. Triflumizole, active ingredient in Procure® 480SC 

fungicide was used in these trials to control powdery mildew in greenhouse tomato production. 

The magnitude of residue data were collected from four greenhouse trials located in Salisbury, 

MD (region 2), Arlington, WI (region 5), Weslaco, TX (region 6) and Parlier, CA (region 1 0). 

Triflumizole is currently registered for applications on a variety of fruit, vegetable, and field 

crops. Tolerances for residues oftriflumizole, including its metabolites and degradates, have 

been established in or on several commodities at 40 CFR § 180.476. The nomenclature and 

physicochemical properties oftriflumizole are presented below in Tables A. I. and A.2. 

TABLE A. l. Test Compound Nomenclature. 

Triflumizole "' 

.. -¢ "Jo~ 

() 

Common name Triflumizole 

Company experimental name Not applicable 

IUPAC name (E)-4-chloro-a,a,a-trifluoro-N-( 1-imidazol-1-t!-2-propoxyethylidene)-o-toluidine 

CAS name 1-[( 1 E)-1-[[ 4-chloro-2-(tri fluoromethyl)phenyl]imino )-2-propoxyethyl]-1 Himidazole 

CAS Number 68694-11-1 

End-use product/(EP) 4 lb a. i./gal Flowable Concentrate (Procure® 480SC; EPA Reg. No. 400-518) 

Metabolite structure r,c~co 

"•" 

Common Name FA-l-l 

IUPAC name 4-chloro-2-(trifluoromethyl)anilinc 

DP Barcode 0413698 I M RW No. 489981-02 Page3ofl0 
Triflumizole/ 128879 I CHEMTURA /400 

DACO 7.4.1/7.4.2/0PPTS 860.1500/0ECD IIA 6.3.1, 6.3.2, 6.3.3 and IHA 8.3. 1, 8.3.2, 8.3.3 

Crop Field Trial- Greenhouse Tomato 

Metabolite structure 

Cl 

:o·~ ~ Common Name FM-6-1 

IUPAC name N-( 4-Ch I oro-2-tri n uorometh yl-phenyl}-2 -propoxy-acetamid i ne 

TABLE A.2. Physicochemical P roperties of Triflumizole 

Parameter Value 

Melting point/range 63.5 °C 

pH N/A 

Bulk Density (at 20 °C) 0.50-0.70 

Water solubility (giL at 20 °C} 0.0125 (at pH 5.9) 

Solvent solubility (gil 00 mL at 20 °C} Chloroform 222 

Acetone 144 

n-Hexane 1.76 

Methanol 49.6 

Xylene 63.9 

Vapor pressure (25 °C} 1.4 x 10-6 mmHg 

Dissociation constant (PKa at25 C) 3.7 

Octanollwater partition coefficient Log 25 

P(K0w) at 25 °C 

UV/visible absorption spectrum (in NIA 

methanol) 

B. EXPERIMENTAL DESIGN 

8.1. Study Site I nformation 

TABL E 8. 1. 1 T rial Site Cond itions. 

Trial Identification (City, State/Year) 

CA 08 (Parlier, CA/2010) 

MD 0 1 (Salisbury, MD/2010) 

TX 03 (Weslaco, TX/201 0) 

WI 03 (Arlington, Wl/20 10) 

Orgamc Maner 2

NA=Not available 

'Cation-Exchange Capacity 

Type 

Sunshine mix # I 

Sungro germinating mix No. 

3/ LG3 

Sunshine mix # I 

G mix 35 potting mix 

Reference 

DEB# 6410, J. Smith. 117192 

Soil characteristics 

%0M 1 pH CEC3 

NA2 NA NA 

NA NA NA 

NA NA NA 

NA NA NA 

The weather conditions at the greenhouse sites were generally considered normal. Plants were 

grown in a greenhouse-controlled environment. Common cultural practices were followed to 

maintain the crop. Additional maintenance pesticides and fertilizers were used at most of the 

sites to produce commercial quality tomatoes (greenhouse). 

At each test location, experimental plants were treated with four foliar directed applications of 

triflumizole, the active ingredient (42.14 %) in Procure® 480SC at 6-8 day intervals, except the 

Texas site where five applications of the test substance were made at 6-14 day intervals and 0-

day PHI. All foliar applications ranged from 0.230-0.258 lb ai/A per application for a total rate 

DP Barcode 041 3698 I MRID No. 489981-02 Page4ofl0 
Triflumizole/ 128879/ CHEMTURA /400 ~ •I 

--I DACO 7.4.117.4.2/0PPTS 860.1500/0ECD IIA 6.3.1, 6.3.2, 6.3.3 and JllA 8.3.1, 8.3.2, 8.3.3 

Crop Field Trial- Greenhouse Tomato 

range of 0.921-1.284 lb ai/ A per season, with the use of a non-ionic surfactant. At greenhouse 

site 09299.10- CA08, a decline trial was conducted with the last application 0, 1, 4, 8, 10 and 15 

days before harvest (0-15 day PHI). The application use patterns are summarized in Table B .1.2. 

TABLE 8.1.2. Study Use Pattern. 

Location Application Tank Mix/ (City, State/Year) EP 1 Volume Rate RTe Total Rate 

TriaiiD Method/Timing GPA2 lb ai/A (days) lb ai/A Adjuvants 

Foliar 

Directed/Blooming/ 50 0.252 ---

Fruiting 

Foliar 

Directed/Blooming/ 5 1 0.255 7 Induce (Parlier, CN20 10) Procure® 480SC Fruiting 1.012 (non ionic CA 08 Foliar surfactant) Directed!Blooming/ 51 0.253 7 

Fruiting 

Foliar 

Directed!Blooming/ 51 0.253 7 

Fruiting 

Foliar Directed/ Fruiting 121 0.230 --- (Salisbury, Foliar Directed/ Fruiting 121 0.230 8 Silwet L77 

Procure® 480SC 0.921 (non ionic MD/2010) MD 01 Foliar Directed/ Fruiting 121 0.230 6 surfactant) Foliar Directed/ Fruiting 121 0.230 7 

Foliar Directed/ Fruiting 89 0.257 --- Foliar 

Directed/Flowering & 89 0.257 14 R-11 (Weslaco, Procure® 480SC Fruiting 1.284 (nonionic TX/20 I 0) TX 03 Foliar Directed/Fruiting 89 0.257 6 surfactant) 

Foliar Directed/Fruiting 89 0.256 7 

Foliar Directed/Fruiting 89 0.256 6 

Foliar Directed/Fruiting 69 0.252 --- (Arlington. Foliar Directed/Fruiting 77 0.258 7 Activator 90 

Procure® 480SC 1.006 (non ionic Wl/20 I 0) WI 02 Foliar Directed/Fruiting 74 0.247 7 surfactant) Foliar Directed/Fruiting 76 0.250 7 I -

EP • End-use Product Gallons per Acre Re-treatmentlnterval 

DP Barcode 0413698 I MRlD No. 489981 -02 Page 5 of 10 
Triflumizole/ 128879 I CHEMTURA /400 

DACO 7.4.1/7.4.2/0PPTS 860.1500/0ECD IIA 6.3.1, 6.3.2, 6.3.3 and IliA 8.3.1 , 8.3.2, 8.3.3 

Crop Field Trial - Greenhouse Tomato 

TABLE 8.1.3. Trial Numbers and Geographical Locations 

US EPA Greenhouse Tomato 

Growing 

Regions Submitted Requested* 

I 

lA 

2 I 

3 

4 

5 I 

SA 

5B 

6 I 

7 

7A 

8 

9 

10 I 

II 

12 

13 

14 

IS 

16 

17 

18 

19 

20 

21 

Total 4 4 

*Four trials are recommended based on an EPA/HED ChemSAC decision ofNovember 16,2005. 

B.2. Sample Handling and Preparation 

Sampling started in the untreated control plot, followed by the treated plot. Two untreated and 

two treated greenhouse tomato samples were collected at all greenhouse trials on the day of the 

last application (0-day PHI). All samples collected at 0-day PHI were dry before crops were 

harvested. Greenhouse tomatoes (12-36 fruits) were harvested by hand from high/low and 

exposed/sheltered parts of 12-14 plants (avoiding 1-2 plants at each end of row) and placed 

directly into residue sample bags. At the California greenhouse trial, two untreated samples (day 

0) and two treated samples were collected on 1, 4, 8, 10, and 15 days PHI. 

The samples were shipped frozen to the analytical laboratory either by ACDS freezer truck or by 

overnight air express packed in dry ice. The TX 03 and WI 03 samples were originally shipped 

to the USDA-ARS laboratory in Beltsville, MD where, the TX 03 samples were chopped with 

dry ice. After reassignment of the analytical laboratory these samples were shipped to the IR-4 

Western Region Laboratory at the University of California, Davis (UCD), CA. 

Samples from all other field trials were received at UCD. Upon arrival at the laboratory, samples 

were opened, inspected, and checked against shipping form. Samples were assigned unique 

DP Barcode 0413698 / MRID No. 489981-02 Page 6 of 10 
·· Triflumizole/ 128879 I CHEMTURA /400 

:==, I DACO 7.4.1/7.4.2/0PPTS 860.1500/0ECD IIA 6.3.1, 6.3.2, 6.3.3 and IliA 8.3. 1, 8.3.2, 8.3.3 

Crop Field Trial- Greenhouse Tomato 

laboratory sample ID numbers and stored frozen. Raw Agricultural Commodity (RAC) samples 

were processed with dry ice in either a Hobart or Robot Coupe food chopper. After the entire 

sample was chopped, a portion was placed in labeled glass pint jars. Surplus was put back into 

the sample bag and both were stored frozen (generally -20 °C). 

B.3. Analytical Methodology 

Samples of greenhouse tomato were analyzed using the method derived from "Determination of 

Triflumizole in Crops," Analytical Method #Meth-115, Revision #3, Morse laboratories, Inc., 

July 18, 2003. The study followed IR-4 National Pesticide Clearance Laboratory Phase Protocol 

PR# 09299 as amended. Modifications made did not negatively affect the performance of the 

method. Residues of triflumizole and its aniline-containing metabolites were converted to F A-ll by acidic and alkaline reflux, followed by distillation. The distillate was acidified and then 

extracted with ethyl acetate. If necessary, further clean-up was achieved by concentrating the 

ethyl acetate layers and using an optional SPE procedure. Total triflumizole residues were 

quantitated using a GC equipped with a MSD in SIM mode. All residues were converted to FAl-l and expressed in parent equivalents. 

The analytical method was validated for triflumizole, FM-6- 1, and F A-1-1 on greenhouse tomato 

at three fortification levels: 0.5 ppm, 1.0 ppm and 10.0 ppm prior to sample analysis. Method 

suitability was evaluated both prior to and concurrently with sample analysis. Based on 

recoveries at the LLMV, the calculated LOD (standard deviation x one-tailed t-statistic) and 

LOQ (3 x LOD) for F A-l-1 on greenhouse tomato were 0.077 ppm and 0.229 ppm, respectively. 

The LLMV was 0.5 ppm. 

During sample analysis, untreated greenhouse tomato samples were fortified with triflumizole 

and FM-6-1 at 0.5 ppm and 1.0 ppm, and F A-1-1 at 0.5 ppm for concurrent recoveries. 

Greenhouse tomato storage stability samples were fortified with triflumizole, FM-6-1 and FA-ll at 1.0 ppm and stored under the same conditions as treated field samples. 

C. RESULTS AND DISCUSSION 

The analytical method was adequate for residue data collection. Method validation recoveries of 

triflumizole, FM-6-1, and FA-1-1 in greenhouse tomato samples fortified at 0.5, 1.0 and 10.0 

ppm averaged 89 ± 10% (n = 9), 86 ± 10% (n = 9), and 91 ± 5% (n = 9), respectively. 

Concurrent recoveries of triflumizole, FM-6-1, and F A-1-1 in greenhouse tomato samples 

averaged 78 ± 4% (n=4), 84 ± 9% (n=3), and 94% (n=1). The results are presented in Table 

C.1. 1, Tables C.1.2 and Table C.1.3 . Residues of triflumizole in all control samples were <0.50 

ppm. 

Samples were stored frozen for up to 556 days prior to extraction for analysis (Table C.2.1). To 

support this storage interval, a concurrent freezer storage stability study was conducted using 

control samples of cucumber fortified separately with triflumizole, FM-6-1, and F A-1-1 each at 

DP Barcode 0413698 / MRID No. 489981-02 Page 7 of 10 
Triflumizole/ 128879 / CHEMTURA /400 

DACO 7.4. 117.4.2/0PPTS 860.1500/0ECD IIA 6.3.1 , 6.3.2, 6.3.3 and IliA 8.3.1, 8.3.2, 8.3.3 

Crop Field Trial - Greenhouse Tomato 

1.0 ppm. The fortified samples were stored under the same conditions (-20°C) 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 control samples freshly fortified with each analyte. Concurrent 

recovery samples had recoveries of 82%, 82%, and 89% for triflurnizole, FM-6-1, and F A-1-1, 

respectively. The average recovery from the stored samples (corrected for concurrent 

recoveries) was 83%, 98% and 84% for parent, FM-6-1, and F A-1-1, respectively; for a mean 

average corrected recovery of 88% for all three analytes (Table C.2.2). These recoveries 

correlate to declines of 17%, 2%, and 16% [average of 12%] over 552 days of storage and 

indicate only slight residue decline in frozen tomato. Because the storage stability study 

demonstrated adequate residue stability, no corrections to the magnitude of the residue data were 

needed. 

Following four broadcast foliar applications of 4 lb ail gal SC triflumizole totaling 1.0 lb ai/ A, the 

combined residues were <0.50 - 0.88 ppm in/on 8 samples of tomato harvested at a 0-day PHI. 

The average residue was 0.59 ppm and the HAFT residue was 0.76 ppm. Triflumizo1e residues 

above the LLMV of 0.5 ppm were found in both trials which used small tomato varieties, while 

residues were below the LLMV in both trials which used large tomato varieties. In the decline 

study, total triflumizole residues were below the LLMV at all sampling intervals; thus, no 

decline trend could be discerned. The detailed residue results from the four greenhouse tomato 

trials are presented in Table C.3. Table C.4 presents a summary of the results. 

TABLE C.l.l. Summary of Recoveries ofTritlumizole from Greenhouse Tomato 

Matrix 

Greenhouse 

Tomato Fruit 

'Method Vahdat10n 2

Concurrent Recovery 

Spike level 

(ppm) 

0.5 

1.0 

10.0 

1.0 

)Storage Stability Concurrent Recovery 

Sample size 

(n) 

3 

2 

3 

I 

3 

I 

Type of Recoveries 

Recovery (%) 

Triflumizole 

MY1 98, 95, 103 

CR- 74,80 

MY 91, 84, 91 

CR 75 

MY 74,85, 77 

SSCR--:r 82 

TABLE C.l.2. Summa ry of Recoveries of FM-6-1 from Greenhouse Tomato 

Matrix 

Greenhouse 

Tomato Fruit 

'Method Vahdat1on 2

Concurrent Re-covery 

Spike level 

(ppm) 

0.5 

1.0 

10.0 

1.0 

'Storage Stability Concurrent Recovery 

Sample size 

(n) 

3 

I 

3 

I 

3 

I 

DP Barcode 0413698 I MRID No. 489981 -02 

Type of Recoveries 

Recoverv (%) 

FM-6-1 

MY 85, 93, 91 

cRI 93 

MY 92,83,91 

CR 76 

MY 61 , 92, 82 

sscw 82 

Mean ± std dev 

(%) 

90 ± 12 

85 ± 7 

79±6 

-

Mean ± std dev 

(%) 

91 ±4 

86 ± 8 

78± 16 

-

Page 8 of 10 
Triflumizolel !28879 I CHEMTURA 1400 

DACO 7.4.117.4.2IOPPTS 860.1500/0ECD !lA 6.3.1, 6.3.2, 6.3.3 and lilA 8.3.1 , 8.3.2, 8.3.3 

Crop Field Trial - Greenhouse Tomato 

T ABLE C.l.3. Summary of Recoveries of FA-l-l from Greenhouse Tomato 

Matrix 

Greenhouse 

Tomato Fruit 

I Method Vahdallon 

Concurrent Recovery 

Spike level 

(ppm) 

0.5 

1.0 

10.0 

Sample size 

(n) 

3 

I 

3 

3 

Type of Recoveries 

Recovery (%) 

FA-1-1 

MV1 90, 86, 90 

c R• 94 

MV 9 1, 94,81 

MV 92,95, 98 

TABLE C.2.1. Summary of Storage Conditions For Greenhouse Tomato 

Matrix Storage Temperature Actual Storage Duration' 

(RAC or extract) (OC) 

Greenhouse Tomato Fruit 

<-20 (triflumizole) 

Greenhouse Tomato Fruit 

<-20 (FM-6-1) 

Greenhouse Tomato Fruit 

<-20 (FA-l-l) 

Calculated I rom sampling to extracuon of treated samples 2

Calculated from fortification to extraction 

(days) 

340-556 

340-556 

340-556 

TABLE C.2.2. Stability ofTriflumizole in G r eenhouse Tomato 

Analyte Spike Storage Freshly Fortified Stored Sample 

Level interval Recovery' (%) Recoveries(%) [A vg] 

(ppm) (days) 

Triflumizole 1.0 552 82 78, 68, s1: r68l 

FM-6-1 1.0 552 82 73, 75, 92: [80] 

FA-l- l 1.0 552 89 74, 77, 73: [751 

Mean ± std dev 

(%) 

90 ± 3 

89 ± 7 

95 ± 3 

Interval of Demonstrated Storage 

Stabiliti (days) 

552 

552 

552 

Average Corrected Mean Avg. 

Stored Recover/ (%) Corrected 

Recovery (%) 

83 

98 88 

84 .. Freshly forttfied concurrent recovery reported as part of the storage stabtltty study (SSCR value), except for F A-1-1 , where no 

SSCR value was reported. For FA-1-1 , the average of three values reported as part of the method validation study, reflecting a 

1.0 ppm spike level, was used. 2 Average stored sample recoveries were corrected for storage stability concurrent recovery (SSCR) values. 

TABLE C.3. Residue Data from G reenhouse Tomato Field T rials w ith Triflumizole 

Tria!ID Total Rate Storage PHJ 

(City, State; Year) Zone Crop/ Variety (lb ai/A) (days) (days) Residues (ppm)' [Avg] 

0 <0.50, <0.50 [<0.50] 

I <0.50, <0.50 [<0.50] 

CA08 Greenhouse 4 <0.50, <0.50 [<0.50] 

10 tomato/Match 1.012 340 

(Parlier, CA/2010) (large) 8 <0.50, <0.50 [<0.50] 

10 <0.50, <0.50 [<0.50] 

1.5 <0.50, <0.50 [<0.50] 

Greenhouse 

MD 0 I (Salisbury. 2 tomato/ 0.921 479 0 <0.50, <0.50 [<0.50] MD/2010) Geronimo 

(large) 

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Triflumizole/ 128879/ CHEMTURA /400 

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Crop Field Trial - Greenhouse Tomato 

TABLE C.3. Residue Data from Greenhouse Tomato Field Trials with Triflumizole 

TriaiiD Total Rate Storage PHI 

(City, State; Year) Zone Crop/ Variety (lb ai/A) (days) (days) Residues (ppm)1 (Avg) 

Greenhouse 

TX 03 (Weslaco, 6 tomato/ 1.2842 556 0 <0.50, 0.67 [0.585) TX/ 2010) Tomatoberry 

(small) 

Greenhouse 

WI 03 (Arlington, 5 tomato/ 1.006 553 0 0.63, 0.88 [0.755) Wl/20 10) Dasher 

(small) 

I The method converts all metabolites mto the common m01ety, F A-1- 1, wh1 ch IS expressed as tnnum1zole equ1valents. 

The statistically calculated LOQ and LOD were 0.23 and 0.077 ppm, respectively; the LLMV was 0.50 ppm. 

Renects 5 applications at approximately 0.25 lb ai/Napplication. 

TABLE C.4. Summary of Residue Data from Greenhouse Tomato Field Trials with Triflumizole 

Total Applic. PHI 

Residue Levels 

Commodity Rate (days) (ppm) 

(lb ai/A) nl Min. Max. HAFT Median Mean Std. Dev. 

Greenhouse 0.92 1-1.284 0 8 <0.50 0.88 0.76 0.50 0.59 0.14 

Tomato 

Number of samples - 2 x number of field tnals. 

D. CONCLUSION 

The greenhouse tomato field trials are adequate with respect to the residue chemistry guidelines 

(860. 1500) and an EP NHED ChemSAC decision regarding the number of trials. The field trials 

support the use of triflumizole in/on greenhouse tomato according to the following use pattern: 

up to four broadcast foliar applications at 0.25 lb ai/A per application [maximum of 1.0 lb ai/A 

per season], a 7-day RTI, and a 0-day PHI. Tri:flumizole residues in greenhouse tomatoes were 

0.88 ppm or less when an SC formulation was applied according to the supported use pattern, 

and residues in small tomato varieties were found to be higher than in large tomato varieties. No 

residue decline trend could be discerned as residues were <LLMV at all sampling intervals in the 

residue decline trial. 

E. REFERENCES 

DEB # 6410, 1.0. No. 400-UGA, Triflumizole, Registration of A8 15 Technical, J. Smith, 1992 

F. DOCUMENT TRACKING 

Petition Number: 2E811 9 

DP Barcode: 0413698 

PC Code: 128879 

Template Version June 2005. 

DP Barcode 0413698 I MRlD No. 489981 -02 Page1 0of l0 
Tritlumizolc/ 128S79 / CHEMTURA /400 

DACO 7.4.117.4.2/0PPTS 860.1500/0ECD IIA 6.3.1, 6.3.2, 6.3.3 and lilA 8.3. I, 8.3.2, 8.3.3 

Crop Field Trial - Greenhouse Cucumber 

Primary Evaluator 

Peer Reviewer 

Approved by 

STUDY REPORTS: 

Shadqu~ Environmental Scientist, 

California Department of Pesticide Regulation 

~a, R<dlo 

Theresa Ratto, Ph.D., Staff Environmental Scientist, 

California Department of Pesticide Regulation 

William H. Donovan, Ph.D., Senior Chemist 

Risk Assessment Branch V, Health Effects Division 

Environmental Protection Agency (EPA) 

Date: 

/~-~-2.c/3 

Date: 

J;J..- /tv~- >o;3 

Date: 

~~-Au&-~ot_;, 

MRID No. 489981-01 , Homa, K. (2012) Tritlumizole: Magnitude of the Residue on Greenhouse 

Cucumber, Amended Final Report. Study No. 268264. Unpublished study prepared by Kathryn 

Homa, IR-4 Project, I 69 pages. 

EXECUTI.VE SUMMARY: 

The Interregional Research Project No. 4 (IR-4) has submitted field trial data for tritlumizole on 

greenhouse cucumber. Four field trials were conducted at greenhouses in the United States in 

EPA Region 2: Salisbury, Maryland (I trial), Region 3: Citra, Florida (1 trial), Region 6: 

Weslaco, Texas (I ttial) and Region 9: Fort Collins, Colorado (1 trial). 

At each test location, experimental p.lants were treated with five foliar directed applications of 

triflumizole, the active ingredient (42.14 %) in Procure® 480SC. All foliar applications targeted 

a rate of 0.25 lb ail A, a 7-day retreatment interval (RTI), and a 0-day pre-harvest interval (PHI), 

without the use of a surfactant. At the Colorado greenhouse site, a decline trial was conducted 

with the last application 0, 3, 7, I 2 and J 5 days before harvest (0-15 day PHI). 

Samples of greenhouse cucumber were analyzed using the method derived from "Determination 

ofTriflumizole in Crops," Analytical Method #Meth-115, Revision #J, Morse la'boratories, Inc., 

July 18, 2003. The study followed IR-4 National Pesticide Clearance Laboratory Phase Protocol 

PR# 09300 as amended. Modifications made did not negatively affect the performance of the 

method. Residues oftritlumizole and its aniline-containing metabolites were converted to FA-1-

1 ( 4-chloro-2-trifluoromethylaniline) by acidic and alkaline reflux, followed by distillation. The 

distillate was acidified and then extracted with hexane. If necessary, further clean-up was 

achieved by concentrating the hexane layers and using an optional silica solid phase extraction 

(SPE) procedure. Total triflumizole residues were quantitated using a gas chromatograph (GC) 

equipped with a mass selective detector (MSD) in selective ion monitoring (SIM) mode. All 

DP Barcode 0413698./ MRI D No. 48998 I -0 I Page I of 12 
Triflumizolel 128879 I CHEMTURA 1400 

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Crop Field Trial - Greenhouse Cucumber 

residues were converted to F A-1- 1 and expressed in parent equivalents. 

The method was validated at 0. 1, 1.0, and 10.0 ppm for triflumizole, FM-6- 1 {(IE) N'-[4-chloro2-(trifluoromethyl)phenyl]-2-propoxyethanimidamide}, and F A-1-1 in greenhouse cucumber 

samples. Average recoveries oftriflumizole, FM-6-1, and FA-1-1 were 76 ± 8% (n = 9), 80 ± 

8% (n = 9), and 74 ± 8% (n = 11 ), respectively. The analytical method is acceptable and 

available for enforcement. The calculated limit of detection (LOD) and limit of quantitation 

(LOQ) for FA-1-1 on greenhouse cucumber were 0.015 ppm and 0.045 ppm, respectively. The 

lowest level of method validation (LLMV) was 0. 1 ppm. 

Samples were stored frozen for up to 881 days prior to extraction for analysis. To support this 

storage interval, a concurrent freezer storage stability study was conducted using control samples 

of cucumber fortified separately with triflumizole, FM-6-1, and F A-1-1 each at 0.5 ppm. The 

fortified samples were stored under the same conditions (-20°C) as the field trial samples. At the 

end of the analytical phase, the stored samples were analyzed along with a control sample and 

control samples freshly fortified with each analyte. Concurrent recovery samples had average 

percent recoveries of 74%, 94%, and 79% for triflumizole, FM-6-1 , and F A-1-1, respectively. 

The average recovery from the stored samples (corrected for concurrent recoveries) was 69%, 

77% and 39% for parent, FM-6-1, and FA-1-1, respectively. These recoveri es correlate to 

declines of 3 1%, 23%, and 61% over 832 days of storage and indicate a potential for residue 

decline in frozen cucumber. Because the method converts parent and all metabolites to a 

common moiety, corrections for the individual residues could not be determined. Therefore, the 

average decline of38% over 832 days (0.0457%/day decrease) was used to correct residue 

values according to the equation Rc = Ru-:- (1 - (0.000457 x DAYS)), where Rc is the corrected 

residue concentration, Ru is the uncorrected residue concentration, and DAYS is the number of 

days in storage. 

Following five broadcast foliar applications of triflumizole totaling 1.25 lb ai/ A, the combined 

residues (uncorrected for storage declines) were <0. 1 0- 0.27 ppm in/on 8 samples of cucumber 

harvested at a 0-day PHI, and with a 7-day RTI. The average uncorrected residue was 0.17 ppm 

and the highest average field trial (HAFT) residue was 0.26 ppm. When corrected for potential 

declines during storage, combined residues in/on all 8 samples were <0.1 4 - 0.39 ppm, the 

average residue was 0.25 ppm, and the HAFT residue was 0.34 ppm. In the decline study, total 

triflumizole residues were at or below the LLMV at all sampling intervals; thus, no decline trend 

could be discerned. 

STUDY/WAIVER ACCEPTABILITY /DEFICIENCIES/CLARIFICATIONS: 

Under the conditions and parameters used in the study, the field trial residue data are classified 

as scientifically acceptable. 

The acceptability of this study for regulatory purposes is addressed in the forthcoming U.S. EPA 

Residue Chemistry Summary Document [DP Barcode 0413698] 

DP Barcode 0413698 I MRJD No. 489981-01 Page 2 of 12 
Triflumizole/ 128879 I CHEMTURA /400 

DACO 7.4. 117.4.2/0PPTS 860.1500/0ECD IIA 6.3. 1, 6.3.2, 6.3.3 and lilA 8.3.1 , 8.3.2, 8.3.3 

Crop Field Trial - Greenhouse Cucumber 

COMPLIANCE: 

Signed and dated Good Laboratory Practice (GLP), Quality Assurance and Data Confidentiality 

Statements were provided. 

This study meets current GLP Requirements of 40 CFR Pa1t 160 except the following deviations, 

which do not affect the conclusions presented in this report. 

1. Supporting data such as weather, irrigation, and soil characterization data were not 

collected in adherence to 40 CFR 160 guidelines. 

2. Test site history, cultural practices, maintenance fertilizers and pesticides, and residue 

sample weighing equipment were not maintained in adherence to 40 CFR 160 guidelines 

at field sites 09300.09 - TX 18, 09300.09 - FL 42, 09300.09 - CO 08, and 09300.09-

MD 13. 

3. The test substance triflumizole (lot# B08M15P034) and reference substances 

triflumizole (lot # 2841 -33-RRG), FM-6-l (Lot# 2842-45-RRG) and F A-1-1 (Lot # 

2842-95-RRG) were not characterized in accordance with 160.135 (a)(b), but were 

characterized in accordance with OECD guidelines, which are accepted by the US EPA 

in a Memorandum of Understanding. 

A. BACKGROUND INFORMATION 

The active ingredient, triflumizole: (N-[4-chloro-2-(trifluoromethyl) phenyl]-N-[1-(1 Himidazole-1-yl)-2-propoxyethylidene] amine), used in this study is an imidazole that is effective 

in inhibiting ergosterol biosynthesis in fungi. The ergosterol is needed for the stabilization of 

membranes that make up cell walls in fungi. Triflumizole, an active ingredient in Procure® 

480SC fungicide was used in these trials to control powdery mildew in greenhouse cucumber 

production. The magnitude of residue data were collected from four greenhouse trials located in 

Salisbury, Maryland (region 2), Citra, Florida (region 3), Weslaco, Texas (region 6) and Fort 

Collins, Colorado (region 9). 

Triflumizole is currently registered for applications on a variety of fruit, vegetable, and field 

crops. Tolerances for residues of triflumizole, including its metabolites and degradates, have 

been established in or on several commodities at 40 CFR §1 80.476. The nomenclature and 

physicochemical properties of triflumizole are presented in Tables A.1 and A.2. 

DP Barcode 0413698 I MRID No. 489981-01 Page 3 of 12 
Triflumizole/ 128879 I CHEMTURA /400 

DACO 7.4.1/7.4.2/0PPTS 860.1500/0ECD IIA 6.3.1, 6.3.2, 6.3.3 and IliA 8.3.1, 8.3.2, 8.3.3 

Crop Field Trial - Greenhouse Cucumber 

TABLE A.l. Test Compound Nomenclature. 

Tritlumizole 01 

.. ~ ·ro~ 

() 

Common name Tritlumizole 

Company experimental name Not applicable 

IUPAC name (£)-4-chloro-a,a,a-trifluoro-N-( 1-imidazol-1-y 1-2-propoxyethy I idene )-o-toluid ine 

CAS name 1-[(1 E)-1-[[4-chloro-2-(trifluoromethyl)phenyl]imino ]-2-propoxyethyl]-1 Himidazole 

CAS Number 68694-11-1 

End-use product/(EP) 4 lb a. i./gal Flowable Concentrate (Procure® 480SC; EPA Reg. No. 400-518) 

Metabolite structure F,CX)OI K,N 

Common Name FA-1-1 

IUPAC name 4 -chloro-2 -(tritl uorometh y I )ani I ine 

Metabolite structure F,c =( .l:f"- ~ Common Name FM-6-1 

IUPAC name N-( 4-Ch I oro-2 -tritl uorometh y (-phenyl)-2-propoxy-acetamidine 

TABLE A.2. Physicochemical Properties of Tritlumizole 

Parameter Value Reference 

Melting point/range 63.5 °C DEB# 6410. J. Smith. 117192 

pH Not available 

Bulk Density (at 20 °C) 0.50 - 0.70 

Water solubility (giL at 20 °C) 0.0125 (at pH 5.9) 

Solvent solubility (g/1 00 mL at 20 °C) Chloroform 222 

Acetone 144 

n-Hexane 1.76 

Methanol 49.6 

Xylene 63.9 

Vapor pressure (25 °C) 1.4 x 10'

6 mmHg 

Dissociation constant (PKa at 25 ·q 3.7 

Octanollwater partition coefficient 25 Log (K0w) at 25 °C 

UV/visible absorption spectrum (in Not available methanol) 

DP Barcode 0413698 / MRID No. 489981-0 I Page 4 of 12 
,a,J Triflumizole/ 128879 I CHEMTURA /400 

~ ~ DACO 7.4. 117.4.2/0 PPTS 860.1500/0ECD IIA 6.3. 1, 6.3.2, 6.3.3 and lilA 8.3.1, 8.3.2, 8.3.3 

'"' Crop Field Trial - Greenhouse Cucumber 

B. EXPERIMENTAL DESIGN 

B.l. Study Site Information 

TABLE 8.1.1. Trial Site Conditions. 

Trial Identification (City, State/Year) 

Soil characteristics 

Type %0M2 pH CEC3 

TX 18 (Weslaco, TX/2009) Not applicable' Not Not Not 

applicable' applicable' appl icable1 

FL42 (Citra, FL/2010) Not applicable4 21.38 5.74 Not 

applicable4 

C008 (Fort Collins, C0/2009) Not applicable5 Not 5.510 6.5 Not 

aoolicable5 aoolicable5 

MD 13 (Salisbury, MD/2009) Not applicable6 Not Not Not 

applicable6 applicable

6 applicable6 

Plants were grown m Sunshane M1x # I (SunGro Hom culture) (so1lless mcd1a). lngred1ents of the m1xture mcludc 70·80 • Yo Canadian sphagnum 

peat moss, perlite, dolomitic limestone, gypsum, and a wetting agent. Scotts Osmocote Plus ( 15-9-12/ 5-6 months @ I% (v/v) was added to the 

potting media. Organic matter, pl-1 and cation exchange capacity of soil were not tested. 1

0rganic Matter 

)Cation-Exchange Capacity 

•rtants were grown in Speedling® Scientifically Formulated Peat-Lite Mix for Professional Growers (greenhouse container media) 1Fafard Canadian Growing Mix 2 (general purpose Canadian sphagnum peat mix) was used in the 5-gallon pots. This mix contained Canadian 

sphagnum peat moss, perlite, vermiculite, starter nutrients, a wetting agent, and dolomitic limestone. 6Piants were grown in rock wool. 

Weather conditions at the greenhouses were generally considered normaL Plants were grown in 

a greenhouse-controlled environment. Common cultural practices were followed to maintain the 

crop. Additional maintenance pesticides and fertilizers were used to produce commercial quality 

cucumbers (greenhouse). 

At each test location, experimental plants were treated with five foliar directed applications of 

triflumizole, the active ingredient (42.14 %) in Procure® 480SC. All foliar applications targeted 

a rate of0.25 lb ai/A, a 7-day RTI, and a 0-day PHI, without the use of a surfactant. At the 

Colorado greenhouse site, a decline trial was conducted with the last application 0, 3, 7, 12 and 

15 days before harvest (0-15 day PHI). The application use patterns are summarized in Table 

8 .1.2. 

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Triflumizole/ 128879 I CHEMTURA /400 

DACO 7.4 .117.4.2/0PPTS 860.1500/0ECD IIA 6.3.1, 6.3.2, 6.3.3 and lilA 8.3.1, 8.3.2, 8.3.3 

Crop Field Trial - Greenhouse Cucumber 

TABLE 8.1.2. Study Use Pattern. 

Location 

(City, State/Year) 

TriaiiD 

(Weslaco, 

TX/2009) TX 18 

(Citra, FU2010) 

FIA2 

(Fort Collins. 

C0/2009) C008 

(Salisbury, 

MD/2009) MDI3 

EP -- End-use Product 1

Gallons per Acre 

·'Rc-treatment Interval 

'NA : Not applicable 

EP 1 

Procure® 480SC 

Procure® 480SC 

Procure® 480SC 

Procure® 480SC 

Method/Timing 

Foliar Directed/Blooming 

and Fruiting 

Foliar Directed/Blooming 

and Fruiting 

Foliar Directed/Blooming 

and Fruiting 

Foliar Directed/Blooming 

and Fruiting 

Foliar Directed/Blooming 

and Fruiting 

Foliar Directed/ Fruiting 

Foliar Directed/ Fruiting 

Foliar Directed/ Fruiting 

Foliar Directed/ Fruiting 

Foliar Directed/ Fruiting 

Foliar Directed/ 

Vegetative 

Foliar Directed/Immature 

fruit 

Foliar Directed/Immature 

fruit 

Foliar Directed/Immature 

fruit 

Foliar Directed/Fruiting 

Foliar Directed/First 

mature fruits 

Foliar Directed/Fruiting 

Foliar Directed/Fruiting 

Foliar Directed/Fruiting 

Foliar Directed/Mature 

fruit 

Application 

Volume Rate RTI3 Tota l Rate 

GPA2 Ib ai/A (days) lb ai/A 

112.9 0.251 A• 

113.0 0.251 6 

112.9 0.251 7 1.255 

113.0 0.251 7 

11 3.0 0.251 7 

98.4 0.249 NA 

99.6 0.252 8 

98.9 0.251 7 1.259 

98.5 0.250 7 

101.6 0.257 6 

95.2 0.239 NA 

100.7 0.260 7 

100.9 0.270 8 1.292 

96.2 0.264 7 

I 01.1 0.259 7 

124.9 0.230 NA 

124.9 0.230 8 

124.9 0.230 7 1.150 

124.9 0.230 8 

124.9 0.230 7 

Tank Mix/ 

Adjuvants 

None 

None 

None 

None 

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Tritlumizolel 128879 I CHEMTURA /400 

DACO 7.4.117.4.210PPTS 860.150010ECD IIA 6.3.1, 6.3.2, 6.3.3 and IliA 8.3.1, 8.3.2, 8.3.3 

Crop Field Trial -Greenhouse Cucumber 

TABLE 8.1.3. Trial Numbers and Geographical Locations 

US EPA Greenhouse Cucumber 

Growing 

Regions Submitted Requested* 

I 

lA 

2 I I 

3 I I 

4 

5 

SA 

58 

6 I I 

7 

7A 

8 

9 I I 

10 

II 

12 

13 

14 

15 

16 

17 

18 

19 

20 

21 

Total 4 4 .. *Four trials are recommended based on an EPAIHED ChemSAC dec1s1on of September 17,2008 

B.2. Sample Handling and Preparation 

Sampling started in the untreated control plot, followed by the treated plot. Two untreated and 

two treated greenhouse cucumber samples were collected at all of the greenhouse trials on the 

day of the last application (0-day PHI). All samples collected at 0-day PHI were dry before 

crops were harvested. Each sample was representative of the entire plot (except plot ends) and 

was collected from at least 12 separate plants. Greenhouse cucumbers were harvested by hand or 

by cutting the fruit from the plant with pruners and 12-24 fruits were collected from each site 

depending on the variety. At the Colorado greenhouse trial, two untreated samples (day 0) and 

ten treated samples were collected on day 0, 3, 7, 12, and 15 days PHI. 

At all field sites except Colorado, fruit were placed directly into the sampling bag. At the 

Colorado field site, after stems and flowers were removed, cucumber fruits were quartered 

and/or halved lengthwise and/or crosswise and opposite quarters or halves including the center 

part with seed placed into the sample bag (minimum of 4 pound 11 ounces per sample). 

At all field trials after sampling procedures were completed, greenhouse cucumber samples were 

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Crop Field Trial -Greenhouse Cucumber 

placed in labeled sample bags and held in frozen storage until shipment to the analytical 

laboratory. Treated greenhouse cucumber samples were placed in frozen storage within I hour 

and 32 minutes of sampling at the Colorado site. All samples were shipped frozen to the 

analytical laboratory at the University of California, Davis (UCD) by ACDS freezer truck or 

Overnight Air Express. Upon arrival the samples were checked in and stored frozen . Raw 

Agricultural Commodity (RAC) samples were processed with dry ice in a Hobart food chopper. 

After the entire sample was chopped, a portion was placed in labeled glass pint jars and surplus, 

if any, was put back into the sample bag and both were stored frozen (generally - 20 °C). 

B.3. Analytical Methodology 

Samples of greenhouse cucumber were analyzed using the method derived from "Determination 

ofTriflumizole in Crops," Analytical Method #Meth-115, Revision #3, Morse laboratories, Inc., 

July 18, 2003. The study followed IR-4 National Pesticide Clearance Laboratory Phase Protocol 

PR# 09300 as amended. Modifications made did not negatively affect the performance of the 

method. 

Residues of triflumizole and its aniline-containing metabolites were converted to F A-1-1 by 

acidic and alkaline reflux, followed by distillation. The distillate was acidified followed by 

extraction with hexane. If necessary, further clean-up was achieved by concentrating the hexane 

layers and using an optional silica solid phase extraction (SPE) procedure. Total triflumizole 

residues were quantitated using GC equipped with a MSD in SIM mode. All residues were 

converted to F A-1-1 and expressed in parent equivalents. 

The analytical method was validated for triflumizole, FM-6-1, and FA-1-1 on greenhouse 

cucumber at three fortification levels: 0.1 ppm, 1.0 ppm and 10.0 ppm prior to sample analysis. 

Method suitability was evaluated both prior to and concurrently with sample analysis. Based on 

recoveries at the LLMV, the calculated LOD (standard deviation x one-tailed t-statistic) and 

LOQ (3 x LOD) for FA-1- 1 on greenhouse cucumber were 0.015 ppm and 0.045 ppm, 

respectively. The LLMV was 0.10 ppm. 

During the sample analysis, untreated greenhouse cucumber fruit were fortified with triflumizole 

at 0.1 ppm, 0.2 ppm, and 1.0 ppm for concurrent recovery spikes. Untreated greenhouse 

cucumber fruit were fortified with FM-6-1 at 0.1 ppm and 1.0 ppm for concurrent recovery 

spikes. 

Greenhouse cucumber storage stability samples and concurrent recovery samples during sample 

analysis were fortified with triflumizole, FM-6-1 and FA-1-1 at 0.5 ppm. 

C. RESULTS AND DISCUSSION 

The analytical method was adequate for residue data collection. Method validation recoveries of 

triflumizole, FM-6-1, and FA-1-1 in greenhouse cucumber samples fortified at 0. 1, 1.0, and 10.0 

ppm averaged 76 ± 8% (n = 9), 80 ± 8% (n = 9), and 74 ± 8% (n = 11), respectively. Concurrent 

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Crop Field Trial - Greenhouse Cucumber 

recoveries of triflumizole and FM-6-1 fortified in greenhouse cucumber samples were 69 ± 5% 

(n = 4) and 87 ± 13% (n = 3), respectively. The results are presented in Tables C.1.1, C.1 .2, and 

C.1 .3. Residues of triflumizole in all control samples were <0.1 0 ppm. 

Samples were stored frozen for up to 881 days prior to extraction for analysis (Table C.2.1 ). To 

support this storage interval, a concurrent freezer storage stability study was conducted using 

control samples of cucumber fortified separately with triflumizole, FM-6-1, and F A- 1-1 each at 

0.5 ppm. The fortified samples were stored under the same conditions (-20°C) 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 control samples freshly fortified with each analyte. Concurrent 

recovery samples had recoveries of 74%, 94%, and 79% for triflumizole, FM-6-1, and F A-1-1, 

respectively. The average recovery from the stored samples (corrected for concurrent 

recoveries) was 69%, 77% and 39% for parent, FM-6-1, and FA-1-1, respectively; for a mean 

average corrected recovery of 62% for all three analytes (Table C.2.2). These recoveries 

correlate to declines of31%, 23%, and 61% [average of38%] over 832 days of storage and 

indicate a potential for residue decline in frozen cucumber. When residue decline in the storage 

stability study exceeds 30%, corrections to the magnitude of the residue data are needed to avoid 

underestimating residue and tolerance levels. 

Because the method converts parent and all metabolites to a common moiety, corrections for the 

individual residues could not be determined. Therefore, the average decline of 38% over 832 

days (0.0457%/day decrease) was used to correct residue values according to the equation Rc = 

Ru + (1 - (0.000457 x DAYS)), where Rc is the corrected residue concentration, Ru is the 

uncorrected residue concentration, and DAYS is the number of days in storage. 

Following five broadcast foliar applications of 4 lb ai/gal SC triflumizole totaling 1.25 lb ai/ A, 

the combined residues (uncorrected for storage declines) were <0.10 - 0.27 ppm inion 8 samples 

of cucumber harvested at a 0-day PHI. The average uncorrected residue was 0.17 ppm and the 

HAFT residue was 0.26 ppm. When corrected for potential declines during storage, combined 

residues inion all 8 samples were <0.14 - 0.39 ppm, the average residue was 0.25 ppm, and the 

HAFT residue was 0.34 ppm. In the decline study, total triflumizole residues were at or below 

the LLMV at all sampling intervals; thus, no decline trend could be discerned. The detailed 

residue results from the four greenhouse cucumber trials are presented in Table C.3. Table C.4 

presents a summary of the results. 

TABLE C.l.l. Summary of Recoveries ofTriflumizole from Greenhouse Cucumber 

Matrix Spike level Sample size Type of Recoveries Mean ± std dev 

(mg/kg) (n) Recovery (%) (%) 

Triflumizole 

0. 1 3 MV 67, 80,61 68 ± 8 I CR- 65 

0.2 I CR 71 71 ± 0 Greenhouse 3 MV 77,85, 78 Cucumber Fruit 1.0 CR 65 76± 8 I 

10.0 3 MV 83, 80, 70 78 ± 7 

0.5 I SSCR3 74 74 ±0 

'Method ValidatiOn 

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Crop Field Trial - Greenhouse Cucumber 

lConcurrent Recovery 

'Storage Stability Concurrent Recovery 

TABLE C.1.2. Summary of Recoveries of FM-6-1 from Greenhouse Cucumber 

Matrix Spike level 

(mg/kg) 

0.1 

Greenhouse 1.0 Cucumber Fruit 

10.0 

0.5 I Method Validation 2

Concurrent Recovery 

'Storage Stability Concurrent Recovery 

Sample size 

(n) 

3 

I 

3 

I 

3 

I 

Type of Recoveries 

Recovery (%) 

FM-6-1 

MV1 65,80, 73 

CR1 94 

MV 86, 84, 89 

CR 72 

MV 86,82, 71 

SSCR3 94 

TABLE C.1.3. Summary of Recoveries ofFA-1-1 from Greenhouse Cucumber 

Matrix Spike level Sample size Type of Recoveries 

(mg/kg) (n) Recovery (%) 

FA-l-l 

0.1 6 MV 155-', 72, 62, 70, 65, 68 

Greenhouse 1.0 3 MV 81, 78,79 

Cucumber Fruit 10.0 3 MV 86,85, 71 

0.2 I SSCR3 79 

Method Vahdat1on 

lThis Recovery was omitted from calculations since it was thought to be double fortified 'Storage Stability Concurrent Recovery 

TABLE C.2.1. Summary of Storage Conditions For Greenhouse Cucumber 

Mean ± std dev 

(%) 

78 ± 12 

83 ±7 

80 ± 8 

94± 0 

Mean ± std dev 

(%) 

67 ± 4 

79 ± 2 

80 ± 8 

79 ± 0 

Matrix Storage Temperature Interval of Demonstrated 

(RAC or extract) (°C) Actual Storage Duration ' (days) Storage Stabilit/ 

(days) 

Greenhouse Cucumber -20 Fruit (Triflumizole) 

Greenhouse Cucumber -20 Fruit (FM-6-1) 

Greenhouse Cucumber -20 Fruit (FA-l-l) 

Calculated from sampling to -extraction of treated samples 2

Calculated from fortification to extraction 

517-881 

517-881 

517-881 

TABLE C.2.2. Stability of Triflumizole in Greenhouse Cucumber 

832 

832 

832 

Analyte Spike Storage Freshly Fortified Stored Sample Average Corrected 

Level interval Recovery' (%) Recoveries(%) [Avg] Stored Recover/(%) 

(ppm) (days) 

Triflumizole 0.5 832 74 45, 53, 55: [5 1) 69 

FM-6-1 0.5 832 94 68, 76, n: rn1 77 

FA-l-l 0.5 832 79 29, 32, 31: [3 1] 39 1 ' . Freshly fortafied concurrent recovery reported as part of the storage stabtltty study (SSCR value). 2 Average stored sample recoveries were corrected for storage stability concurrent recovery (SSCR) values. 

DP Barcode 0413698 I MRID No. 489981-01 

Mean Avg. 

Corrected 

Recovery(%) 

62 

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Crop Field Trial - Greenhouse Cucumber 

TABLE C.3. Residue Data from Greenhouse Cucumber Field T rials with Triflumizole 

Trial iD Total Rate Storage PHI 

Residues (ppm) 1 

(City, State; Year) Zone Crop/ Variety (lb ai/A) (days) (days) Corrected for storage Uncorrected (Avg] declines 2 [Avg] 

09300.09-TX 18 Greenhouse 

(Weslaco, TX/2009) 6 cucumber/ 1.255 881 0 0.11 , <0. 10 [0.11] 0. 18, <0.17 [0.18] 

Diva 

09300.09-FL 42 Greenhouse 

(Citra, FU2010) 3 cucumber/ 1.259 517 0 0.27, 0.25 l0.26] 0.35, 0.33 [0.34) 

Jawell 

0 0.10, <0.10 [0.10] 0.14, <0. 14 [0.14] 

09300.09-CO 08 Greenhouse 3 <0. 10, 0. 11 [0. 11) <0. 14, 0. 15 (0.15] 

(Fort Collins, CO/ 9 cucumber/ 1.292 630 7 <0.10, <0.10, [<0. 10] <0.1 4, <0.14 [<0. 14] 

2009) Camaro 12 <0.10, <0.10, [<0. 10) <0.14, <0.14 [<0. 14] 

15 <0.10, <0. 10, [<0. 10] <0. 14, <0.14 [<0. 14] 

09300.09-MD 13 Greenhouse 

(Salisbury, 2 cucumber/ 1.150 777 0 0.17, 0.25 [0.2 1] 0.26, 0.39 [0.33] 

MD/2009) Jawell 

The method converts all metabolites mto the common m01ety, F A-1-1, wh1ch IS expressed as tnflum1zole eqUivalents. The 

statistically calculated LOQ and LOD were 0.045 and 0.015 ppm, respectively; the LLMV was 0. 10 ppm. 2 As the method converts parent and all metabolites to FA-1-1 and the average corrected recovery of each analyte varied (39-

77%), the average decline (38% ( 100% - mean avg corrected %recovery) over 832 days) was used to correct residues. 

Residue values were corrected based on the actual storage duration of each samples and assuming a decline of0.0457%/day of 

storage according to the equation Rc = Ru + (I - (0.000457 x DAYS)), where Rc is the corrected residue concentration, Ru is 

the uncorrected residue concentration, and OA YS is the number of days in storage. 

TABLE C.4. Summa r y of Residue Data from G reenhouse Cucumber Field Trials with Triflumizole 

Total Applic. PHI 

Residue Levels 

Commodity Rate (days) (ppm) 

{lb ai/A) nl I Min. I Max. I HAFT I Median 1 Mean 1 Std. Oev. 

Uncorrected Results 

Greenhouse 1.150-1.292 0 8 I <o.1o 1 0.27 I 0.26 I 0.14 I 0.17 I 0.09 

Cucumber Corrected Results 

1.150-1.292 0 8 I <0.14 I 0.39 I 0.34 1 0.22 1 0.25 I 0.10 

Number of samples- 2 x number of held - tnals. 

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Crop Field Trial - Greenhouse Cucumber 

D. CONCLUSION 

The greenhouse cucumber field trials are adequate with respect to the residue chemistry 

guidelines (860.1500) and an EPA!HED ChemSAC decision regarding the number of trials. The 

field trials support the use of triflumizole on greenhouse cucumber according to the following 

use pattern: up to five broadcast foliar applications at 0.25 lb ai/A per application [maximum of 

1.25 lb ai/A per season], a 7-day RTI, and a 0-day PHI. Triflumizole residues in cucumber, 

corrected for decline in frozen storage, were 0.39 ppm or less when an SC formulation was 

applied according to the supported use pattern. No residue decline trend could be discerned as 

residues were at or below the LLMV at all sampling intervals in the residue decline trial. 

E. REFERENCES 

DEB # 6410, 1.0. No. 400-UGA, Triflumizole, Registration of A815 Technical, J. Smith, 1992 

F. DOCUMENT TRACKING 

Petition Number: 2E8119 

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PC Code: 128879 

Template Version June 2005. 

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