### UNITED STATES ENVIRONMENTAL PROTECTION AGENCY WASHI NGTON , D .C. 20460 OFFICE OF CH EM ICAL SAFETY AND POLLUTION PREVENTION 

### MEMORANDUM Date: Subject: 29 -0CT -20 1 3 Triflumizole. Section 3 Registration for Greenho u se Uses on Tomato and Cucumber; Translations of Apple and Pear to Pome Fruit Group 11 - 1 

### 0, Grape to Crop S u bgroup 13-07F, and Strawberry to Crop Subgroup 13-07G, Exce pt Cranberry . Summary of Analytical Chemistry and Residue Data . PC Code : 128879 DP Barcode : 0 413698 Decisi on No . : 472282 Registr ation No. : NA Petition No. : 2E8119 Regu latory Action: Section 3 Registration R isk Assessment Type: NA Case No.: NA TXR No.: NA CAS N o.: 68694-11-1 MRID Nos.: 48998101 &48998102 40CFR: §180.476 

### FROM :
TH ROUGH:

TO : Willi amH.Donovan,Ph.D.,Chemis t

# 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 D i vision (7509P) Andrew Ertman!Barbara Madden, 

### RM 05 Risk Integrati on , M i nor Us e, Emergency Response Branch Registration D ivision (7505P) And Seyed Tadayon, Ri sk Assessor Risk Assessment Branch (RAB) V Health Effects D iv i s i on (7509P)

Page I of 18Triflumizole 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 estab li shing tolerances for trifl um izole in or on greenhouse grown cucumber and tomato, and for converting the estab li shed tolerances for apple and pear to the same tolerance level for pome fruit crop group 11-10, for converting the established tolerance fo r grape to the same tolerance level for crop subgroup 13-07F, and for convertin g 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 th e new use requests for triflumi zo le. The nature of the residue in plants is adequately understood for th e purposes of this petition based on previously reviewed plant metabolism studies . Fi eld tr i al s 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 met hod i s availab le to enforce triflumizole tolerances. In a stability study conducted concurrently with the cucumber magnitude of the residue study, combined triflumizo le residues declined on average by 38% in cucumber samples stored at -20°C for 832 days, or 0 . 0457% per day. Based o n this factor , corrections were made to th e cucumber field trial data to account for res idue dec line in frozen storage . Tolerance recommendati ons 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 rotati onal crop studies support the rotational crop restrictions specified on current labels. The proposed label for greenhouse grown cucumber and tomato shou ld be revised to omit the rotational crop restriction since greenhouse soils are not typically reused. 

### 2.0 Regulatory Recommendations Pendi ng submission of a revised Section Bas detailed 

### in Section 2.3, there are no res idu e chemistry co n s iderations that would preclude establishment of the recommended tolerances. 

### 2.1 Data Deficiencies/Data Needs There are no residue chemistry deficiencies identified for this peti t ion . 

### 2.2 Tolerance Considerations 2 .2.1 Enforcement Analytical Method An adequate GC/NPD method i s available (Method I in PAM Vol. II) fo r determining the combined residues of triflumi zol e 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 metabo li tes to F A
- 1- 1 coup led w ith distillation of FA-1-1 into hexane. Page 2 of 18Triflumizole Summary of Analytical Chemistry and Residu e Data 0413698 

### Residues are fi ltered through anhydrous sodium sulfate, purified using a silica gel SPE column, and de termined as FA- 1
- 1 by GC/NPD. Residues are expressed in terms oftriflumizole. The method LOQ is 0.5 ppm for p l ant commodities. 

### 2.2.2 Recommended Tolerances The proposed to lerances and commodity defin it i ons are appropriate and match HED recommendat ions. Table 2.2.2 summarizes triflumizole tolerances resulting from the current petition . Table 2.2.2. Tolerance Summary for Triflumizole'. Commodity Proposed Recommended Comments; Corre ct Com modify To lerance ( ppm) To lerance (ppm) Definilion Tomato 1.5 1.5 Greenhouse tomatoes only. Fruit, pome, group Il-l 0 0.5 0.50 Fruit, small, vine climbi ng, except fuzzy kiwifruit, 2.5 2.5 subgroup 1 3-0?F Berry, low growing, subgroup 13
-0?G, except 2 .0 2 . 0 cranberry Includes established field uses for Vegetable, cucurbit, group 9 0.50 2 0 . 50 cucurbits and the proposed greenhouse use on cucumber. Th ese tolerances s hould be established under 40 CFR § 180.476. 2 The established and propose d tolerances for crop group 9 are identical and cover the proposed use on greenhouse grown cucumber. 

### Note to RD : Upon estab lishment of the recommended to lerances listed above, to lerance listi n gs for the fo ll owing individual crops should be revoked since they will be included in the new crop group and crop subgroups listings: apple, pear, grape, and s trawberry. In addition, some recommendations for changes made in a previous review are not cur rently reflected i n 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; app le, wet pomace; grape, dried pomace; grape, raisin, waste; and grape, wet pomace . The commodity listed as "cil antro, leaves" shou ld be changed to "coriander, leaves.'' A l so, 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; mil k; poultry, fat; poultry , meat; poultry, meat byproducts ; and sheep, meat. T o lerance levels for the following commodi t ies shou l d be lowered from 0 . 5 to 0.10 ppm: fat of cattle, sheep, goat, and horse . Tolerance levels for the following commodi t ies should be lowered from 0 . 5 to 0.20 ppm : meat byproducts of ca ttle, sheep, goat, and ho r se. 

### 2.2.3 Revisions to Petitioned-For Tolerances None 

### 2.2.4 International Harmonization Page 3 of 18Tritlumizole Summary of Analytical Chemistry and Re s idue 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 tol erance levels (see Appendix A). Trifl umizole i s not registered for use in Canada. The Canadian MRLs for triflumizole were set to support the import oftreated commodities . 

### 2.3 Label Re commenda tions HED recommend s that the rotational crop re strictio n be omitted from the greenhouse grown cucumber and tomato use directions si nce soils in greenhouses are not typically reused. 

### 3.0 Introduction 3 . 1 Chemical Identity Table 3.1 Triflumizole and Metabo lite Nomenclature Chemical structure FC

# ~N**r~b- CI** **N~-\_** 0 \ CH 2CH2CH 3 Empirical formula C1sH 1 sN 30CIF 3 Common name Tr itlumizo le IUPA C 1 name (E)-4-chlor o-a,a,a-tritluoro-N-( I- im idazol-1- y l-2- propoxyethyl idene) -o toluidine CAS 2 name 1
- [(IE)
- 1
- [[4
- chloro-2-(tritluoromethyl)phenyl]imino)-2-propoxyethyi]-1Himidazole CAS registry number 68694- 1 1-1 End -use products (EPs) Procurellll SOWS; EPA Reg . No. 400-431 Procure® 480SC ; EPA Re g. No . 400-518 Metabolite structure F3 C 

# N=(**~**

# ~ 0

## ~

# ~ Cl Common Na m e FM-6- 1 IUPAC name N- (4-Chloro-2-tritluoromethyl-phenyl)-2-propoxy-acetamidine



### Page 4 of 18Triflumizole Summary of Analytical Chemistry and Resi due Data 0413698 Tab le 3 . 1 Triflumizole and Metabolite Nomenclature Chemical class Imidazole Common moiety structure F 3 C 

# H,N_:oCI

Common name FA-l-1 IUPAC name 4-chloro-2-tri fluoromethy Ian il ine Livestock metabo lite CF 3 

# CI-Q-NH 2 OH Common name FA-1-5 IUPAC name 4-chloro-2-hydroxy-6-trifluoromethylaniline Livestock metabolite CF 3 

# CI-Q-NH 2 

### S0 3 

### H OH Common name FA
- 1
- 5-S IUPAC name 4-ch loro-2-hydroxy
- 6
-trifluoromethyJanil ine sui fate 1 T

UPAC = International Union of Pure and Applied Chemistry 2 CAS = Chem ic al Abstracts Service 

### 3.2 PhysicaUChemical Characteristics Physiochemical properties for triflumizole are shown in Tab l e 3 . 2.

TABLE 3.2. Physicochemica l 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 solub il ity (g/L at 20 °C) 0.0125 (at pH 5 .9) Solvent solubility (g/1 00 mL at 20 <>q Chlo roform 222 Acetone 144 n-Hexane 1.76 Methanol 49.6 X

ylene 63 .9 Vapor pressure (25 °C) 1.4 x 10· 6 mmHg Dissociation constant (pK. at 25 · q 3 .7 Octanol/water partition coefficient Ko w at 25 25 

### o c UV/visib le 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 18Tr iflumizole Summary of Analytical Chemistry an d Re sidue Data 0413698 

### 3.3 Pesticide Use Pattern/Direction s for Use (860.1200) Tab le 3.3 . S umma ry o f D ir ectio n s f or Proposed Uses o f T riflumi z ole. App li c. Timi ng; Formu lat ion Applic. M ax. No. M ax. Seasonal PHI Type : and [EPA Reg. R ate App li c. per App lic. Rate (days) Us e Di rec ti o ns and Li mitations Equip. No . ] (lb ai/ A) Season ( l b ai/ A) P o me fruit crop grou p ll -1 0 Broadcast fo liar; 4 lb /ga l F I C 0 . 5 4 2 . 0 14 A m inimum RTI of I 0 da ys is At fir s t indication [400
- 518] s p ec ified . App ly in a of disease ; minimum of SO ga llA f or Ground or aerial gro und app licatio ns . equ ipmen t Sma ll fruit v in e climbing , exce pt fu zzy kiwif ruit, c r op s ub group 1 3-0 7F Low-growing berr y crop s ubgroup 1 3-07G, except c ran berry Broadcast fo li ar ; 4 l b/gal F I C 0.25 4 1.0 1 4 A minimum RTI of2 1 days is [400-5 1 8] s pecified . App l y in a At first indication m inimum of 50 ga l / A for of disease ; g r o und app li cations. Ground and Aerial ( ae rial a pplication for grape is equipment pro hibited ) Gree nhouse g r own vege table (C u c umb er a nd Tomat o) Manually a nd 4 l b / gal SC 0.25 

### s 1. 25 0 D o no t plant leafy or non - leaf y mecha nic ally [400
- 521] Bras sica vegetables or fru iting pressurized hand vegetab l es w ithi n 3 0 days afier gu n s prayer app lication. Do not pl a nt bulb vegetab l es or root vegetab l es w ith in 60 days after app lication. Do no plant cotton , small cereal grains and a ll o ther crop s not registered o n th e l a b el within one year aft er application . RE I : 12 hou r s . Minimum RTI : 7 days. 

### Th e use d irection s are adequate to allow evalu ation of th e residue data relative to the proposed uses. The prop osed m axim um application rates, RTis, and PHi s are s upp orte d by the submitted fi e ld trial data. Because g reenho use soils are not reused , there is no need for a rotational crop restrict ion for greenho u se grown vegetab les. HED re commends removal of the p ropos ed rotational crop restriction for greenhous e cucumber and tomato. 

### 4 .0 Meta bol ite/Degradate Residue Profile 4.1 Nature of the Residue 4.1.1 Summary of P lan t Meta b olism (860 .1300 ) The nature of the re sidue in p lants is adequ ately unde rst ood for purpo ses of the crops that are th e subject of thi s petition. Acceptable metab o li sm data are av ailable on apples , cucumbers , grapes , and pears (PP#5G3232, N. Dodd , 7/ 3/ 85 ). Th e Agency determined that the residues of conc ern include triflumi zo le and it s metabo li tes co ntain in g the 4-chloro
-2-tr ifluoromethylaniline moiety , P age6of l8Triflumizole Summary of Analytical Chemistry and R es idu e Data D413698 calcula ted as triflumi zo l e. This conclusion was reaffirmed in a meeting of the Metabo li sm Assessment Review Committee (MARC) on 2/26/ 02 (D 280869, J. Tyler, 3/ 13 / 02) . 

### 4.1.2 Summary of Livestock Metab olism (860 . 1 300) There are no li vestock feedstuffs associated with th e prop o sed uses. T herefore, data requirements for li vestock metabol ism are not re leva n t 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 c ro p studies were submit t ed in conjunction with a tolerance petition for use oftriflumizo l e on str awbe rri es (PP# 1F06297, D274589, 

### J. Ty l er, 3111/02; D327173, J. Ty l er, 10/19 / 06) . Based on th e resu l ts ofthe confined st u dy, the MARC (meeting 2/26/ 02) concluded th at th e re sidues of concern in rotational crops i nclude tri flumizole and all met abo li tes containi ng the 4
- chloro -2- trifluoromethylanili ne moie ty for purposes of ri sk assessment a nd the t olerance expression . 

### 4 . 2 Residues of Concern Summary and Rationale The Metabolism Assessment Review Commi ttee (MA RC) determined that res i dues of concern should include parent triflumi z ole and all metabolites conta i ning the 4-chl oro-2- trifluoromethy l aniline moiety (D280869, 

### J. Tyler, 3/13 / 02). Metabolites conta i ning t he 4-chloro2-trifluoromethylaniline moiety are unli kel y 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 i nclude these compounds in th e ri sk assessment. Furth er, it is al so appropriate to include these metabo li te s i n the tolera n ce express i on since a common moiety enforcement method is available. 

### Table 4 .2 Summary of Metabolites and Degradates to be included in the Risk Assessmen t and Tolerance Expression Matri x Res idu es inc l uded in Risk Ass ess m e nt R es idu es in cluded in Tole ranc e Exp ressio n Plants (Primary and Triflumizole and all metabo l ites Triflumizol e and all metabolites contain ing containing the 4
- chloro
- 2
- the 4
- chloro
- 2
- tri fluoromethylani line Rotational Crops) trifluoromethylan iline moiety moiety Triflumizole, 4 -c hloro-2- Tritlumizole , 4-chloro-2- Livestock trifluoromethylan iline sulfa te , and other t rifluoromethy lani l ine su lfate, an d other metabolites containing the 4-chloro-2- metabolites containing the 4-chloro
- 2
- trifluoromethylaniline moiety tri fluoromethylaniline moiety T riflumizole and all metabolites Drinking Water containing the 4-ch loro-2- Not Applicable trifluoromethylaniline mo iety

Page 7 of 18Triflumizole 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 fie l d trials were analyzed for the combined residues of triflumizole and its metabolites convertible to FA-1
- 1 using a GC/MSD method (Morse Labo ratories Analytical Method Meth
- 115, Rev i sion #3). T his method i s de rived 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 ace t ic acid/sodium n itrate for 90 minutes . While still reflux ing, 20% sodium hydrox i de (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. Res i dues are expressed in parent equ i valents by multiplying the amount ofF A-1-1 by a molecu l ar weigh t convers i on facto r of 1. 77. The lowest limit of method validati on (LLMV) was 0.1 and 0 . 5 ppm fo r the cucumber and tomato trials, respective ly . Based on acceptable concurrent method recovery data, the analytical method is adequate for data collection. 

### 5 . 1.2 Multi-Residue Methods (860 .1 360) Data are available on the recovery oftri fl umi zo le through FD A Mu ltiresidue Method Testing Protocols . The FDA PES T DA T A database dated 06/2005 (PAM Vol. I, Appendix I), ind ica tes that triflumizo le is completely recovered using Multiresidue Method Sec t ion 302 (Pro tocol D) w ithout 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 trifl umi zo le and its me taboli tes contain ing the FA-1-1 moiety in p l an t commodit i es (G . Kramer, 12/16/94). This common moiety method involves alkali ne hydrolysis of parent and its metabolites to FA
- 1
- 1 coupled with d i still ati on ofF A- 1
- 1 i nto hexane. Res i d ues are fi ltered through anhydrous sodium sulfate , purified us i ng a silica gel SPE column , and de termined as FA
- 1-1 by GC/NPD. Residues are expressed in terms oftriflumizole. The method LOQ is 0 . 5 ppm for plant commodities.

P age 8 of 18Triflumizole Summary of Analytical Chemistry and Residue Data 0413698 

### 5.1.4 Submittal of Analytical Reference Standards (860.1650) Analytical s tan dards fo r tr iflumizo l e (CAS # 1 08-62
- 3) and its re gu l ated metaboli tes are avail able at the EPA National Pest i cide Standards Repository [personal communi cation from T . Cole of ACB/BEAD to S. Tadayon, 08/20/2013] wi th the fo ll ow i ng rece ipt and expiration dates: 

### Inventory Chemical Name Notes Company Date Reed Date Exp triflumi z ole Chemtura 8 /1 6/2013 1/31/2018 triflumizole metab o lite FA-1-1 Chemtura 5/9/2011 9/30/2015 triflum i zole meta b oli t e FA-1- 5 Chemtura 5/9/2011 8/31/2015 triflumizole metabolite FA-1- 5 sulfate Chemtura 9 / 14/2010 8/31/2015 triflumi z ole metabolite F M -6-1 Chemtura 9/10/20 10 5 /3 1/2014 Pr ior to t h e li sted exp irat ion dates, fresh s t andards should b e re - sub m itted to the Repository. The reference standard(s) s h ould be sent to the A nalytical Chemistry Lab, which is located at Fo r t Meade, to the attenti on of T heresa Cole at the followi ng add ress: USE PA Nat ional Pes t icide S tandard s Re p osi tory/Analyti cal Chemi stry B ranch/OPP 70 1 Mapes Road Fort George G . Meade, M D 2 0755-5350 The full 9 dig i t zip code is man datory or th e mai l will be returned . 

### 5 . 2 Storage Stability (860.1 3 80 ) Adequate storage stability data are available i nd i cating th at tri flumizole i s stab l e under froze n s torage condi t ions for at leas t 12 months in apples, grapes, and cherries (PP#6F3372, S. Mal ak, 1125 / 90 ; and 0242429, J. Tyler, 3111/02), 1 0 mo n ths in cucurb i t vegetables and st r awberries (0271003, J. T yle r , 3111/02; and 0 27 4 589, J
. T yl e r , 3/11/ 0 2), and 3.2 months in filberts (0312293, J. T yle r , 5118/05). However , significant residue decline in frozen storage has also been ob served in the fo ll owing matrices: mus tard greens (44% decli n e in 9 . 5 month s] (D338653, J. Tomerlin, 07-DEC-2007), brocco li [ 58% decl i ne i n 7 . 6 month s ], and cabbage (5 0 % decline in 8 months ] (0346779, W . Cutchin, 01-0CT-20 08 ) . When residue decl ine in the storage stabili t y study exceeds 30%, correc t ions to the magn itu de of th e r esidue data are needed to avoid u nderesti mating residue and toler ance levels . Storage stability studies were conducted in conju n ctio n w ith the submi tted cucum b er and toma to field trials . For these studies, cont ro l samp l es of cucum b er and tomato were forti fi ed separatel y with tri flumizole an d its me tab oli tes> FM-6- 1 an d FA- 1 -1, each at 0.5 ppm, and stored un der th e same conditions (
- 20°C) as the field t rial samp l es. At th e end of the analytical p hase, the sto r ed
P age 9 of 1 8Triflumizo le Summary of Analytical Chemistry and Residue Data 0413698 

### samples were analyzed in triplicate along wi th a control sample and samples fresh ly fortified 

### with each analyte. Acceptable residue stab ili ty was observed over the 552 

### day sto rage interval in the tomato storage stability as residue decline was asse ssed to be 12% . In contrast, the cucumber storage s tability study showed significant decline. Thus, the average recovery from the stored samples (co rrected 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 st orage and indicate a potential for res idue decl i ne in frozen cucumber. Becau se the me th od converts parent and all me tabolites to a common moiety, corrections for the individual residues could not be determined. T herefore, the average decline of 38% over 832 days (0.0457% / day decrease) was used to correc t residue values according to t he equati on Rc 

## = R u -:- (1 - 

### (0 . 000457 x 

### DAYS)), where Rc is th e corrected residue concentration, Ru is the unco rrected residue concentration, and DAYS is the number of days in sto rage. In the submitted cucumber field trials, samp le s were he ld in s torage at -20°C for 517 -8 81 days (:S29 months) prior to extract ion for analys i s. Corrected re sidues were calculated usin g the ac tual sto rage interval for each sample and a decline factor of0.0457%/day. 

### Conclusions . The avail ab le storage stability data are adequate. Although ea rl ier studies in dicated th at t riflumizo le is stable under frozen storage in cucurbit vege tables fo r at least 10 months , the cucumber samples in the greenh ouse trials were stored for significant ly longer perio ds of time . The storage stabi li ty data submitted i n support of the greenhouse cucumber tri als indicate that residues decline on average by 0 .0457% per day; therefore, to properly assess triflumizole residue leve l s i n the cucumber magnitude of the residue studies, reported res idue 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 Tr ials) 

### Cucumber Greenhouse T rials T h e Interregional Research Project No.4 (IR-4) submitted magnitude of the residue data for triflumizole on greenhouse cucumber. Four gree nh ouse trials we re conducted in the United · S tates in EPA Region 2: Salis bury, Maryland (1 trial), Region 3 : Citra, Fl orida (1 trial), Region

6: Weslaco, T exas (1 trial) an d R egion 9: F ort Collins , Co l orado (1 trial). The tri al s reflect the use offive foliar direc ted app lications of trifl umizole, at a rate of 0.25 lb ai/A, a 7-day re treatment interval (R TI ), and a 0
- day pre-harvest interval (PH I ), without the use of a surfactant. At the Colorado greenhouse site, a decline tri al was conducted with th e last app li cation 0, 3, 7, 12 and 15 days before harvest (0-15 day PHI). Samples we re stored frozen for up to 88 1 days pri or to extraction for analysis . Based on the results of the concurrent storage stability study, residues of parent an d the metabolites FM-6 -1 and FA-1 -1 were shown to decline over 832 days of frozen (-20°C) sto r age by 31%, 23% and Page 10 of 18Triflumizole Summary of Analytical Chemistry and Residu e Data 0413698 

### 61%, re spectively (38% averaged decline). As the analytical method converts parent and all metabolites to a common moiety, an average d ecline of 0.0457% per day (38%/832) was used to c orrec t re sidue values according to the equation R c 

### = R u + 

### (1
- (0.000457 x 

### DAYS)), where Rc i s the conected res i due concentration, Ru is the uncorrected residue concentration, and DAYS is the number of days in storage. The GC/MSD method us ed to determi ne the combined residues of triflumizo le and its metabolites convertible to FA -1
- 1 was adequately validated prior to and in conjunction with the analysis of field trial samples . The st atisticall y calcu lated LOQ for parent was 0.045 ppm, and the calcu l ated LOD was 0.015 ppm. The LLMV was 0.1 ppm. Fo ll owing five broadcast fo li ar applicati ons of triflumizole to taling 1.25 lb ai /A, the combined residues (uncorrected for sto r age 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 fi eld trial (HAFT) res i due was 0.26 ppm. When corrected for potential declines during storage, combined re sidues 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 triflumizo le residues were at or below the LLMV at all sampli n g i ntervals; thus, no decline trend could be discerned. T he results from these studies are summari zed in T ab le 5.3.1.1. TABLE 5.3 . 1.1 Summary of Residue Data from Gree nhouse Cucumber Field Tria ls with Triflum izole Total Applic . PH I 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 o f samp le s 2 x numbe1 of field tnals . 

### Conclusions: 

### The number of cucumber greenhouse trials an d the ir geographical distribution are adequate (four trials we re recommended in an EPA/HED ChemSAC decision of September 17, 2008). The storage stabili ty study i ndi cated that residues declined during frozen sto r age a t 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 app ropriate (see Appendix B). However, HED concl ud es that the es tab li shed tolerance of 0 .5 ppm for cucurbit vegetables group 9 is adequate to cover greenhouse cucumber for th e following reasons: 1) the greenhouse cucumber HAFT is 0 . 34 ppm (less than the establ i shed crop group 9 tole rance), and 2) keep i ng the establ i shed crop group 9 tole rance at 0 . 5 ppm retain s harmonization with the PMRA MRL. To mato Greenhouse Trials IR-4 submitted field trial data for triflumizo le on greenhouse tomato . Four greenhouse tri als were conducted in the United States in EPA region 2: Salisbury, Maryland (I 

### trial), region 5: Arlington, Wiscons i n (1 

### trial), region 6 : Wes l aco, Texas ( 1 trial), an d region 10: P arli er, Calif ornia ( 1 trial). The trials reflect the use of four fo li ar directed appl ic ations of triflumizole, at a rate of 0.25 lb Page 11 of 18Triflumizole 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 l ast 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 extracti on for analysis . Based on the resu lts 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 wi th the analysis of field trial samples. The statistica ll y 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 app li cat i ons 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 PH I. 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 sma ll tomato varieties, while residues were below the LLMV in both trial s that used large tomato varieties. In the decline study, total triflumizole residues were below the LLMV at all sampl ing intervals; thus, no decline trend could be discerned . The results from these studies are summarized in Tab le 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 a i /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 t11al s. 

### 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 triflumizo le at a rate of0 . 25 lb ai/A (for a seasonal rate of 1.0 lb ai/A) rather than the labe l 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 i mportant factor for triflumizole residues in this crop, wi th higher residues likely in small tomato varieties. The tomato data set was analyzed using the OECD MRL calculation procedures to determine the recommended tolerance leve l of 1.5 ppm for greenhouse grown tomato (see Appendix B). Tolerance Conversions to Crop Groups/Subgroups Page 12 of 18Triflumizole Summary of Analytical Chemistry and Residue Data 0413698


### • Apple and Pear to Pome Fru it 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 triflumi z ole use pattern is identical for apple and pear (and for the propos ed 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 th e 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 1 3-07F, 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 th e representative commodity for crop subgroup 13-07F . • Strawberry to Crop Subgroup 13-07G, Except Cranberry [Berry, low growing, subgroup 13 -07 F, except cranberry] IR-4 p roposed that the es tab lished tol erance of2.0 ppm for strawber ry be converted to crop subgroup 13-07G, except cranberry, also at 2.0 ppm. This request is supported by extension of the s tra wberry use pattern to include crop subgroup 13-07G, except cranberry, as indicated in the proposed revisions to th e Procure® 480SC label, submitted as part of Section B of the petition. S trawberry 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 gr oup/subgro up tolerances, the ind ividual crop tolerances for apple, pear , grape, and strawberry should be revoked as they w ill be included i n the group/ subgroup tolerance lis tings. 

### 5.3.2 Field Rotati o nal Crops (860.1900) 0341963, J.R . To m erlin, 07-DEC-2007 

### Adequate limited field r otationa l crop studies were submitted in conjunction with a tolerance petition for use oftriflumizo le on s trawberries (PP#1F06297, 0274589, J. 

### Ty ler, 3111/02; 0 327173, J. 

### Ty ler, 10/19/06). Results from the limited ro tational crop field tri als 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 wi th out registered uses for triflumizole . The current labels include ro tat ional crop restrictions that are consistent with the above PBi s; the proposed label directions fo r greenhouse grown cucumber and tomato do not need to include rotati onal crop restrictions since soils in greenh ouses are not typically reused (email message from B. Sc hneider toW. Donovan , 16 -SEP- 2013, and from B. Barney (IR
- 4) to A. 

### Ertman, 24-SEP-2013).

Page 13 of 18Triflumizole Summary of Analytica l Chemistry and Residue Da ta 0413698


### 5.3.3 Processed Food and Feed {860.1520) There are no processed commo dit ies assoc i ated with greenhouse cucumber or tomato. Although greenhouse tomatoes could potentially b e processed, economic considerati ons limit this possibility (email message from B. Schneider toW. Donovan, 01-AUG-20 1 3). 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 res idu e chemistry data have been provided fo r triflumizole. Field trials are of adequate number and geographic representati on . Data analyses employed validated analytical methods and are supported by adequate storage stabili ty data. Residues oftriflumi z ole demonstrated satisfactory stability 

### in frozen storage except fo r fortified samples of cucumb er, where residues declined 38% over 832 days . According ly, magnitude of the residue data for cucumber was corrected for degradation duri n g frozen storage . No tom ato process i ng 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 follow in g tolerances shou ld be deleted from 180.476(a)(l ): app le, dry pomace; apple, wet pomace; grape, dried pomace ; grape, rais in , waste; and grape, wet pomace. The commodity listed as "cilant ro, 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 shou ld 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, sma ll cereal grains, and any oth er crops without registered uses for triflumizole. 

### 6.0 Tolerance Derivations T he recommended tolerances for trif1urni z ole were derived by 1) use of the OECD MRL calcu l ati on 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 calcula tion procedures . However, HED concludes that the estab li shed tolerance of 0 . 5 ppm for cucurbit vegetables group 9 is adequate to cover greenhouse Page 14 of 18Triflumizole 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 estab lished 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 Lim its Tabl e. B. Tolerance Calculations. Attachments 4899810 1.der.d ocx 489981 02 .der.do cx

Page 15 of 18Triflumizole Summary of Analytical Chemistry and Residue Data 0413698 Appendix A. International Residue Limits Table


### Triflumizole (128879; 09112/ 2013) Summa1y of US and Inte rnational Tolerance s and Maximum Residue Limit s Residue Definition : 

# us Canada Mexico l Codex 40 CFR 40 CFR § 180.4 76 1-[ 1-[[4-chloro-2- None Plants: parent compound tritlumi zole, 1-( 1-((4- (trifluoromethyl)phenyl] imino ]-2- ch loro
-2 -(trifluoro methy l )phenyl)imino )
- 2- propoxyethyl]-1 H-imidazole, propoxyethyl)-1 H -imid azole , and its including metabo lites metabolites containin g the 4-ch lo ro-2- containing the 4-chloro-2- trifluoromethylaniline moiety , calculated as trifluorome th y lanilin e moi ety, sto i chi ometric eq uival ent of the parent expressed as triflumizole compo und. 

### Commodity 1 

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

# us Canada Mexico 2 

### Codex Tomato 1.5 Fru it , pome, group Il- l 0 0.50 0.5 apples, pears Fru it , small, vine c limbing, except 2.5 2.5 grapes fuzzy kiwifruit , s ub group 13-07F Berry , low growing, subgroup 13
- 2.0 2 strawberries 07G, except cranberry 0.5 balsam app les , balsam pears , canta l oupes, chayote fruit , Chinese cucumbers , Chinese waxgourds, ci tron Vegetable, cucurbit, group 9 0.50 melons , cucumbers, edible gourds , muskmelons (other than those listed in this item) pumpkins, summer squash. waterme lons , west Indian gherkins, winter squash Com pleted : M. Negussie; 09/ 13/13 1 In c lud es only co mm od iti es of interest for this ac ti on. Tolerance values should be the HED r ecommen dation s and not thos e propose d by the app l icant. 2 Mexico adopts US tolerances and/or Codex MRLs for it s export purposes.



### Page 16 of 18Appendix B. R es ults 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 M R

L e s t ima te . [Small dataset]
Residues {mg/kg) N 0.14 1 0.18 1 0.3 3 1 0. 3 4 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 . 7 43 0 . 7 43

0 . 8Triflumi zo le Summary of Anal yti cal Che mistry and R es idu e 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

Hi gh un ce r tainty of M RL estimate. [Small data se t ]
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

1.5 041 3698.. .**~** 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 Reg ulatio n
Theresa Ratto, Ph.D., StaffEnvironmental Scientist, California Department of Pesticide Regulation Will iam 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 Interre gional Research Project No.4 (IR-4) has submitted field trial data for triftumizole on greenhouse tomato. Four greenho use 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 pl an ts 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, I0, 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 Laborato ry 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 FA-ll (4 -chloro-2-trifluorometh y lanili ne) by acidic and alkaline reflux, followed by distillation. The
DP Barcode 04 I 3698 f MRID No. 489981-02 Page I of 10Triflumi zo le / 12 88 7 9 I CHEMTU RA /400 DACO 7.4 . 1 17 .4. 2/0PPTS 860.1500/0E C D IIA 6 . 3. 1 , 6.3.2 , 6.3.3 and 111 A 8 .3. 1 , 8.3.2 , 8.3.3 Crop Field Trial
- Greenhouse Tomato 

### distillate was acidified and then extracted with ethy l acetate. If necessary, furth er clean-up was achieved by concentrating th e ethyl acetate lay ers and using an optional silica solid phase extraction (SPE) procedure. Total triflumi zole residues were quantitated using a gas chromatograph (GC) equ ipp ed with a mass selective detector (MSD) in se lective ion monitoring (SIM) mode. A ll residues were converted to FA-1-1 and expressed in parent equiva lents. The method was va l idated at 0.5 , 1.0, and 10.0 ppm for triflumizole, FM-6-1 {( IE) N' -[ 4-chloro2-(trifluoromethyl)phenyl)-2-propoxyethanimidamide}, and FA-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), respective ly. The calcu l ated limit of detection (LOD) and limit of quantitation (LOQ) for FA-1-1 on greenhouse tomato we re 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 w ith thi s study . The maximum storage interval for greenhouse tomato samples du rin g the study was 556 days. Average reco veries f rom storage s tability greenhouse tomato samp les fortified at 1.0 ppm and sto red 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 , re spectively. Because the storage stability study demonstrate d adequate residue stability, no corrections to the magnitude of the res idu e data were needed. The field trials support the use of triflumizole in/on greenho use tomato according to the fo ll owing use pattern: up to four broadcast foliar applications at 0.25 lb a i / A per application [m aximum of 1.0 lb ai/ A per season], a 7-day RTI, and a 0-day PHI. Triflumi z ole residues in greenhouse tomatoes we re 0.88 ppm or less whe n an SC formulation was applied according to the supported use patt e rn , 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 discernib le. STUDY/WAIVER ACCEPT ABILI TY/DEFICIENCI ES/CLARIFI CA TIONS : Under the conditions and parameters used in the study , the field trial residue data are classified as scientifi cally acceptable. The acceptability of this study for regulatory purposes i s addressed in the forthcoming U . S . EPA Residue Chemistry Summary Document [DP Barcode D413698]. COMPLIANCE: Signed and dated Good Laborato ry Practice (GLP), Quality Assurance and Data Confidentiality Statements were provided . This study meets current GLP Requirements of 40 CFR Part 1 60 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 10Tritlumizole / 128879 / CH EMTURA / 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 fie l d tri al s, supporting data such as soi l characterization , weather , irrigation, cultural practices , si te history r ecords, and maintenance chemical app li cations were not collected in strict adherence to 40 CFR 160 gu idelines. 2. At all field trials , the scales used to roughly estimate the weight of the samp les at the field trial site were not ca librated or maintained under GLP. 

### A. BACKGROUND INFORMAT IO N The ac tiv e ingredi en t, triflumizole : (N- [4-chloro-2-(trifluoromethyl) phenyi)-N-[1-(l Himid azole- 1 -y l)-2-propoxye th y lid ene] amine), used in this study is an imidazo l e that i s effective in inhibiting ergostero l biosynthes is in fungi. The ergosterol is needed for the stabilization of membranes that make up cell walls in fungi. Triflum izole, 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 Sa li sbury , MD (reg ion 2), Arlington, WI (reg ion 5), Weslaco , TX (regio n 6) and Parlier, CA (region 1 0). Triflumizo le is currently registered for applications on a variety of fruit, vegetable, and field crops. To l erances for re s idu es oftri flum izole, includ i ng i ts metabo lites and degradates, ha ve been estab li shed in or on seve ral commodities at 40 CFR 

### § 180.476. The nomenclature and physicochemical properties oftriflumizole are presented below in Tables A. I. 

### and A.2.

TA BL E A. l. Test Compou nd No me nclature. Triflumizole "'


# ..-¢**"Jo ~**  

# () Commo n name Triflumizole Company experimental name Not applicable IU

PAC 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 E

nd-use product/(EP) 4 lb a. i./gal Fl owable Concentrate (Procure® 480SC; EPA Reg. No. 400-518) Metabo li te structure**r, c~co**  "•" Co mmon Name FA -l-l IUPAC name 4
-chloro
-2
- (t rifluorom et h yl)anil inc

DP Barcode 0413698 I M RW No. 489981-02 Page3ofl0Triflumizole / 128879 I CHEMTURA /400 DACO 7.4.1/7.4.2/0PPTS 860.1500 / 0ECD II A 6.3.1, 6.3.2, 6.3.3 and IHA 8.3. 1 , 8 . 3.2, 8.3.3 Crop Fi eld Trial- Greenhouse Tomato Metabolite s tru cture

# :o·~ Cl

# ~ Common Name FM
- 6-1 IUPAC name N
- ( 4-Ch I oro -2- tri 

### n uorometh y l-phen y l }
- 2 -propoxy- acetamid ine TA BL E A.2. Ph ys icochemical P rop erties of Triflumizo l e 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 so lu bility (gil 00 mL at 20 °C} Ch loroform 222 Acetone 144 n-Hexane 1.76 Methanol 49 . 6 Xylene 63.9 Vapor pressure (25 ° C} 1.4 x 10 -6 mmHg Di ss ociation constant (PKa at25 C) 3.7 Octanollwa t er partition coefficient Log 25 P(K 0 w) at 25 °C UV/visible absorption spec trum (in N IA methanol) 

### B. EXPERIMENTAL DESIGN 

### 8. 1. Stud y Site I nformati on

TAB L E 8. 1. 1 T ri al S ite Co n d itions.

Tria l Identificat i on (City , State/Year) CA 08 (Parlier, CA/2010) MD 0 1 (Sa li sbury, MD/ 2010) TX 03 (Wes l aco , TX/201 0) WI 03 (Arlington , Wl/20 10 ) Orgamc Maner 2NA=Not available 'C ation-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

So il characteristi cs %0 M 1 pH CEC 3 NA2 NA NA NA NA NA NA NA NA NA NA NA


### T h e weather conditions at the greenhou se sites were generally considered normal. Plants were g r

own in a greenhouse-contro ll e d environment. Co mmon cultural practices we re fo ll owed to mai ntain t he crop. Add iti onal maintenance pesticides an d fertilizers were used at most of the s ites to produc e commercial quali ty tom atoes (greenho u se). At each test location, experi mental plants were treated with fo ur foliar directed app li cations of triflumizole, the acti ve ingredient (42 . 14 %) 

### in Procure® 480SC at 6-8 day i ntervals, except the Texas site where five applications of the test substance were made at 6-14 day intervals and 0- day PH I. All foliar applications ran ged from 0.230-0.258 lb ai/A per application fo r a total rate
DP Barco de 041 3698 I MR ID No. 489981-02 Page4ofl0Triflumizole / 128879/ CHEMTURA /4 00 

## •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 decl i ne 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 summar ized in Table B .1.2. TABL E 8. 1.2 . Stud y Use Pattern. Location Application Tank Mix/ (City, State/Year) EP 1 Vo l ume Rate RTe Total Rate Tria ii D Method/Timing GPA 2 lb ai/A (days) lb ai/A Adjuvants Foliar Directed / Blooming/ 50 0.252
--- Fruiting Foliar Directed/Blooming/ 5 1 0 .2 55 7 Induce (Parlier, CN20 10) Procure® 480SC Fruiting 1.012 (non ionic CA 08 Folia r 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 T X/20 I0) TX 03 Foliar Directed/Fruiting 89 0.257 6 surfactant) Foliar Directed/Fruiting 89 0.256 7 Foliar Directed /F ruiting 89 0.256 6 Fo liar Directed/Fruiting 69 0.252 

### --- (Ar lington. Foliar Directed /F ruiting 77 0.258 7 Activator 90 Procure® 480SC 1.006 (non ionic Wl /20 I 0) WI 02 Foliar Directed/Fruiting 74 0 .2 47 7 surfactant) Foliar Directed/Fruiting 76 0.250 7 I - EP • E nd-u se Product Gallons per Acre Re-treatmentlnterval

DP Barcode 0413698 I MRlD No. 4899 81
- 02 Page 5 of 10Triflumizole / 128879 I CH E MTURA /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. Tria l N um bers and Geograp h ical Locatio n s US EPA Green hou s e T omato Growing Regions Submitted Reque sted* 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 T otal 4 4 *Four trials are recommended based on an EPA/ HED ChemSAC decision ofNovember 16,2005. 

### B.2. Sample Handling and Preparation 

### Sampling sta rted in the untreated control p l ot , followed by t he treated plot. Two untreated and two treated greenhouse tomato samples were collected at all greenhouse trials on the day of the last app lication (0-day PHI). All samples collected at 0
- day PHI were dry before crops were harvested. Greenhouse tomatoes (12-36 fru its) we re harvested by hand from h i gh/low and exposed/sheltered parts of 12-14 plants (avoidi ng 1-2 p l ants at each end of row) and placed directly into residue sample bags. At the California greenhouse trial, two un treated samples (day 0) and two treated samp les were collected on 1, 4, 8 , 1 0, and 1 5 days PHI. The samp les were shipped frozen to the analytical l aboratory either by AC D S freezer truck or by overnight air express packed i n dry ice . T he T X 03 and W I 03 samples were orig inally shipped to the USDA-ARS laboratory 

### in Beltsville, MD where, the TX 03 samples were chopped with dry ice. After reass i gnmen t of the analytical l aboratory these samp les were shipped to the IR-4 Western Region Laboratory at the Universi ty 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 shippi n g fo rm . 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 Tria l
- Greenhouse Tomato 

### laboratory sample ID numbers and stored frozen. Raw Agricultural Commodity (RAC) samples were proces sed with dry ice in either a Hobart or Robot Coupe food c h opper. After t he entire sample was chopped , a portion was placed in labeled gl ass pint jars. Surplus was put back into the samp le bag and both were store d frozen (gene rally -20 °C). B.3. A nal ytical Methodology Samples of greenhouse tomato were analyz ed using the method derived from " Determination of Triflumizole in Crops ," Analytical Method #Meth -115, Revision #3, Morse laboratories, Inc. , July 18, 2003. The study followe d IR-4 National Pesticide Clearance Laboratory Ph ase Protocol PR# 09299 as amended. Modifications made did not negatively affect th e performance of th e method. Residues of triflumizo le and its aniline-containin g metabolites were converted to FA- l
l by acidic and alkaline reflux, followed by distillation. The distillate was acid ified 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 triflumi zole residues were quantitated using a GC equ ipped with a MSD in SIM mode. All residue s were converted to FAl-l and expressed in parent equivalents. The analytical method was validated for triflumizole, FM-6- 1, and FA-1-1 on greenho use t omato at three fortification levels: 0.5 ppm, 1.0 ppm and 1 0.0 ppm prior to sample analysis. Meth od su itability 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-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 FA-1-1 at 0.5 ppm for concurrent recoveries. Greenhouse tomato storage stability samples were fort ified with triflumizole, FM-6-1 and FA-ll at 1.0 ppm and stored unde r 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), r espectively. Concurrent recoveries of triflumizole, FM-6-1, and FA-1-1 in greenhouse tomato samples ave r aged 78 ± 

### 4% (n =4), 84 ± 

### 9% (n=3) , and 94% (n=1). The results a re presented in Tab le C.1. 1 , Table s C.1.2 and Table C.1.3 . Residues of triflumizole in all control samples were <0 . 50 ppm. Sa mples were stored fro z en fo r up to 556 days prior to extraction for analysis (Table C.2.1). T o support this storage interval , a concurrent free z er storage stability study wa s con ducted usin g 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 10Triflumizole / 128879 / CH E MTURA /400 DACO 7.4. 1 17.4.2/0P PTS 860 . 1500 / 0ECD II A 6 . 3.1 , 6.3.2, 6 .3 .3 and IliA 8.3 . 1, 8.3.2, 8.3.3 Crop Field Trial
- Greenhou se Tomato 

### 1.0 ppm. The fort ified samples were stored u nder th e same con d it ions (
- 20°C) as the field trial samples. At the end of the analytical ph ase, the stored samples were analyze d in triplicate a long with a contro l sampl e and control samples freshly fortified with each analyte. Concurrent recovery samples had recove ries of 82%, 82%, and 89% for triflurnizo le , FM-6
- 1 , and FA
- 1
- 1, respectively. The ave rage recovery f rom the sto red samples (corrected f or concurren t recoveries) was 83%, 98% and 84% for parent, FM-6 -1, and F A
- 1
- 1, respectively; for a mean average co rrected recovery o f 8 8% for all three analytes (Table C.2.2). T he se recoveries correla te to decli n es of 1 7%, 2%, and 16% [average of 12% ] over 552 days of storage and indicate only slight re sidue decline in froze n tomato. Because the sto r age stability study demonstrated adequate res i due stability, no correcti on s to the magni t ude of the residue data were needed. Following four broadcast foliar app li cations of 4 lb ailgal SC triflumizole totali ng 1. 0 lb ai/ A, the combined residues we re <0.50
- 0.88 ppm in/on 8 samples o f tomato harv ested at a 0-day PHI. Th e ave rage residue was 0.59 ppm and the HAFT res idue was 0.76 ppm. Triflumizo1e residues above the LLMV of 0 . 5 ppm were found in both trials which used sma ll tomato varieties, w hil e residues we re below the LLMV in both trials which use d large tomato varieties. In the dec li ne study, total triflumizole residues were below the LLMV at all samplin g intervals; thus, no decline trend could be discerned. The detail ed residue results from the four greenhouse tomato trials are presented i n Table C.3. Table C.4 presents a s u mmary of the results .

TABLE C.l.l. Su m mary of Re co veries ofT ritlumi zo le from Greenh ou se Tomato Matrix

Greenhouse Tomato Fruit

' Method Vahdat10n 2 Co ncurrent Recovery Spike level (ppm)

0.5 1.0 10 . 0 1.0 )S t

orage Stabil i ty Concurrent Recovery Sample size (n) 3 2 3 I 3 I Type of Recoveries Reco very (%) Triflumizole

MY 1 98, 95, 103 CR
- 74,80 MY 91, 84, 91 CR 75 MY 74,85, 77 SSCR--:r 82

TABLE C.l.2. S umm a ry o f Recove rie s o f F M -6- 1 from G re e nhouse T oma to Matrix

Greenhouse Tomato Fruit

' Method Vahdat1on 2Concurrent 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 N o. 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 10Triflu mizo lel !28879 I CHEMTURA 1 400 DACO 7.4.117.4.2I O PPTS 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. S umm ary of Recoveries of FA
- l- l from Gree nh o u se To m ato Matri x
Greenhou se 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 MV 1 90 , 86 , 90 c R • 94 MV 9 1 , 94,8 1 MV 92,95 , 98

TABLE C.2.1. S um mary o f Sto r age Co ndi tions For Gree nh o u se Tomato Matrix Storage Tempera ture Actu al Sto rage Duration' (RAC or extract) ( OC) Greenhouse Tomato Fru i t < - 20 (triflumizole) Greenhou se Tomato Fruit <- 20 (FM- 6 -1) Green house Tomato Fru it <-20 (FA-l-l) Calculated I r o m sa mpling to extracuon of treated samp le s 2Calculat ed from fortification to ex trac tio n (days) 340 -55 6 340 -55 6 340-556

TA B LE C.2.2. Stab ili ty ofT ri flumizo le i n G r ee n ho u se To m ato Ana l yte Sp ike S torage Fres hl y Fortifi ed Stored Sample Leve l interval Recovery' (%) Re coveries( %) [A vg] (p pm) (day s) Triflumi zo l e 1.0 552 82 78, 68, s1 : r68l FM
- 6- 1 1.0 552 82 73, 75, 92 : [8 0] FA-l- l 1.0 552 89 74, 77, 73: [751 Mean ± std dev (%) 90 ± 3 89 ± 7 95 ± 3

I nterval of De mon s trated Storage Stabilit i (days) 552 552 552

A verage Co rrected Mean Avg. Sto red Recover / (%) Correct ed Recovery ( %) 8 3 98 88 84

.. Freshly forttfied concurrent recovery reported as part of th e sto rage stabtltty study (SSC R value ), except for FA -1-1 , where no SSCR val ue was reported. For FA -1-1 , the av erage of three val ues rep orted as part of the method validatio n st ud y, reflectin g a 1.0 ppm spike l eve l , was us ed. 2 Average s tored sa mple recov eries w e r e co rrected fo r s tor age s tability concurre nt r eco very (SSCR) values.
TABLE C.3. Res idu e Data from G r eenhouse To m ato Fie ld T r ial s w ith Triflumizole Tria!ID Total R ate Storage PHJ (City, State ; Year) Zone C rop/ Variety (lb ai/ A) (days) (days) R esidue s (pp m )' [A vg] 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/M atch 1.012 340 ( Parlier, CA/20 10) (lar ge) 8 <0.50, <0. 50 [ <0. 50] 1 0 <0.50 , <0 . 50 [<0.50] 1 . 5 < 0 . 50, <0 . 50 [< 0 . 50] G re e nhouse MD 0 I (Salisb ury . 2 t omato/ 0 . 921 479 0 <0.50 , < 0.50 [ <0 . 50] MD/ 2010) Gero nim o ( large)

DP Barcode 0413698 I MRlD N o. 489981-02 Page 9 of 10Tri fl u mizole/ 12 887 9/ C HEM T URA /4 00 DACO 7.4.1/7 .4. 2/ 0P P TS 860. 1 5 00/0EC D IIA 6.3.1 , 6 . 3 .2 , 6.3.3 a nd Ili A 8.3 . 1 , 8.3.2, 8 . 3.3 C ro p Field T r ia l
- Gree nhou se T o ma to TABL E C.3 . Residue Dat a from Greenhou s e Tomato Fie ld Tri a ls with Triflumizol e T ri aiiD T otal Ra te S to rag e PH I ( C it y, Stat e; Yea r) Zon e C r op/ Variety ( lb ai/ A) ( d ays) (days) Resi du es (ppm) 1 (A v g)
G ree nhouse T X 03 (W es l aco , 6 tom ato / 1.284 2 556 0 <0 . 5 0 , 0.67 [0.585) TX/ 20 10) To m ato berr y (small) G ree nhouse W I 03 (Ar lin g t o n , 5 tomato/ 1.006 5 5 3 0 0.63 , 0 . 88 [0 .755) Wl / 2 0 10) Dashe r ( s ma ll) I The meth o d con ve rts a ll m etabolites mto th e co mm o n m01et y, FA-1- 1 , wh1 ch I S ex p re ssed as tnnum1 zo le eq u1va lent s. The s ta ti s ti call y c a l c ul ated LOQ an d LOD we re 0 . 23 and 0.077 p pm, respec t ively; the LL MV was 0 .5 0 ppm . R

enec t s 5 a pp lic ations at approxima te ly 0.25 lb ai/Napp li cation. TABLE C .4. S ummary of R es idu e Data from Gre en h ouse Tomato F ield Trials with Triflumizole Total A ppli c . PH I R e s idue Leve ls Commodity Rate ( days ) (ppm) (l b ai/ A ) nl Mi n. M ax . HAFT Medi an Me an S td. Dev . Gre enh o u se 0 . 92 1
- 1.284 0 8 <0. 5 0 0. 88 0.76 0 .5 0 0. 59 0. 14

T o mato



## - N umb er o f sa mpl es 2 x num be r o f fi e ld tnals . 

### D. C ONC LUS I ON Th e green ho u se to mato field trials are a d equate wi th respect to the res idu e c hemist ry gu id e li ne s (860. 1 500 ) an d an E P NH E D C he mS AC dec i s ion regard ing the numbe r of tri a l s . The fi e ld tria l s s up p ort the use of tri flu m i z o l e in/o n greenhou s e to m ato acco rd in g to the fo ll owi ng u se p attern: up to fou r broadc a s t foliar appl i c ation s at 0.25 lb ai /A p e r ap p lication [m ax imu m of 1.0 lb ai/ A p e r s e a so n ] , a 7
- day RTI , an d a 0
- day PHI. Tri:flumi zole res idu es in greenh o u se tomatoes were 0.88 pp m o r less whe n an SC fo rmul ation was ap pli e d acc o rdi ng to the s upp orte d u s e patt e rn , an d residue s i n s m a ll tomato vari e ti es were foun d to b e higher th an in lar ge to mato v ariet ies. No res i due de c line trend could b e discerned as re s id ues we re < LLMV at all samp li ng i nterval s i n the res i due de cline tri a l. 

### E . RE FERENCES DE B # 6410 , 1.0. 

### No . 400- U GA, Trifl um izole , Reg is t rat ion o f A8 15 T echnical , J . Smi th , 1 992 

### F. DOC U MENT TRA C KING Petition Nu mber : 2E811 9 DP B arcode: 04 13 69 8 PC Code: 128 879 T

empl a t e Versio n Jun e 200 5 . DP Ba rcod e 04136 98 I MRlD No. 489981
- 0 2 Page1 0of l 0Tritlumizolc/ 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~Env ironmental 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 ailA, 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 J5 days before harvest (0-15 day PHI) . Samples of greenhouse cucumber were analyzed using the method deri ved 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 d id 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 tr iflumizole residues were quanti tated 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 12Triflumizolel 128879 I CHEMTURA 1 400 DACO 7. 4.1 17.4 .2 1 0PPTS 860.1500 10ECD 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 residues were converted to F A-1- 1 and expressed in parent equ ivalents. The meth od was validated at 0. 1 , 1.0, and 10.0 ppm for triflumi zole , FM-6- 1 {(IE) N'
- [4
- chloro2-(trifluo r omethyl)pheny l]-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 ), respecti vely. The analytical method is acceptable and available for enforcement. The calculated lim i t of detection (LOD) and lim it of quantitation (LOQ) for FA-1-1 on g reenhouse cucumber were 0.015 ppm and 0.045 ppm, respectively. The lowest level of method validation (LLMV) was 0. 1 ppm. Samp les were s tored froze n for up to 881 days prior to extraction for analys i s. To s uppo rt this storage in terval, a concurrent freezer storage stability study was conducted us i ng contro l samples of cucumber fortified separately with triflumizole , FM-6
- 1, and F A-1-1 each at 0.5 ppm . The fortified samples were sto red 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, respective ly. These recove ri es correla te to declines of 3 1 %, 23%, and 61% over 832 days of s torage and in dicate a potenti a l for residue decline in frozen cucumber. Because the method converts parent and a ll metabo li tes to a common moiety, corrections for the individual residues cou l d 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 = R u-:- (1
- (0.000 457 x D AYS)) , where R c is the corrected residue concentration, Ru is the uncorrected re sidue concentration, and DAYS is the number of days in storage. Following five broadcast foliar applications of triflumizole totaling 1.25 lb ai/A, t h e combined residues ( u ncor rected for storage decl in es) we re < 0. 1 0- 0.27 ppm in/on 8 samp les of cuc u mber harvested at a 0-day PH I , and with a 7-day RTI. The average uncorrected residue was 0.17 ppm and the highest average fie ld tria l (HAFT) residue was 0.26 ppm. When corrected for potentia l 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 residue s were a t or below the LLMV at all sam pli ng interval s; thus, no decline trend could be discerned. 

### STUDY/WAIVER ACCEPTABILITY /DEFICIENCIES/CLARIFICATIONS : Under the conditions and parameters used in the study, the field tria l residue data are classified as scientifically acceptab le. The acceptability of this study for regulatory purpo ses is addressed in the forthcoming U.S. E PA Residue Chemistr y Summary Document [D P Barcode 0413698]

DP Barcode 0413698 I MRJD No. 489981-01 Page 2 of 12Triflumizole / 128 8 79 I CHEMTURA /400 DACO 7.4. 1 17.4.2 / 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 Fiel d Tria l
- Greenhous e Cucumber 

### COMPLIANCE: Sig n ed and dated Good Laboratory Practice ( GLP ), Quality Assurance and D ata Co nfidenti ality Statements were provided. This study meets curre n t GLP Requirements of 40 CFR Pa1t 160 excep t the fo llowing deviations, which do n o t affect the conclusions presented in thi s report. 1. Supportin g data such as weather , irrigation, and so il characterization data were not collected in adherence to 40 CFR 160 guide lines. 2. Test si t e history , cu ltural pract ices, maintenance ferti li ze rs an d p es ticides , and residue sam pl e weighing equipment we re not maintain ed in adherence to 40 CFR 160 guidelines at fie ld s ites 09300.09
- TX 18 , 09300.09
- FL 4 2, 09300.09
- CO 08, and 09300.09- MD 1 3. 3. The te st substance triflumizole (lot# B08M15P034) and reference substances triflumizole ( lo t # 2841
- 33 -RRG) , FM-6-l (Lot# 2842-45-RRG) a nd FA -1-1 (Lot # 2842-95 -RRG ) were not characterized in accordance with 160 . 135 (a)(b), but were c haracterized i n accordance w ith OECD guideli nes, whic h a re accepted by the US EPA in a Memorandum o f Understanding. A. BACKGROUND INFORMATION Th e ac ti ve in gred ie nt , triflumizole: (N-[4 -chl oro-2-(trifluoromethyl) ph e ny l]-N- [1-(1 Himidazole-1-yl)-2-propoxyethy lidene] amine) , us ed in this study is an imidazole that is effective in inhibiting e r goste rol biosynthesis in fungi. The ergosterol is needed for the stabilization of m emb ranes th a t make u p cell walls in fungi. Triflumizole, an active ingredient in Procure® 480SC fu n g icide was used in these tri al s to control powde ry mild e w in greenhouse cucumber production. Th e magnitude of residue data were collected f ro m four gree nhouse trials located in Salisbury , Mary lan d ( re g i on 2), Citra, Florid a (region 3), Wes laco, T exas (reg i on 6 ) and Fort Collins, Co lorado (region 9) . Tri flum izo le is cu rrentl y registered for applications on a variety of fruit, vege t able, and field crops. To leranc es for residues of triflumizole , includin g its metabo li tes and degradates, ha ve been establ i shed in or on several commo d ities at 40 CFR §1 80.476. The no men clature and physicochemical properties of triflumizole are presented in Table s A.1 and A.2 .

DP Ba r code 0413698 I MRID No. 489981-01 Page 3 of 12Triflumizole / 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 0 1



# ..

# ~**·r o~**  

# () Common name Tritlumizole Company experimental name Not applicab le IUPAC name (£)-4-chlor o-a,a,a-trifluoro-N-( 1
- imidazol
- 1
- y 1-2-propoxyethy Iidene )-o-tol uid ine CAS name 1
- [(1 E)-1-[[4-chloro-2-(trifluoromethyl)phenyl]imino]
-2-propoxyethy l]
- 1Himida zole CAS Number 68694-11-1 End-use product/(EP) 4 lb a . i./gal Flowable Concentrate (Procure® 480 SC; EPA Reg. No. 400-518) Metabolite structu r e 

# F ,CX)O I

K,N Common Name FA-1-1 I UPAC name 4-chloro- 2-(tritl uo r ometh y I)ani I ine Metabolite structure F,c 

# =( 

# .l:f"
-**~** Common Name FM-6-1 IUPAC name N-( 4-Ch Ioro- 2-tritl uorometh y (
- phenyl)
-2
-propoxy-acetamidine TABLE A.2 . Physicochemical Properties o f Tri tl um i zo le Parameter Value Reference Melting poin t/r ange 63.5 °C DEB# 6410. J. Smith. 1 17192 pH Not available Bulk Density (at 20 °C) 0 . 50
- 0.70 Water solubi lity (giL at 2 0 °C) 0.0125 (at pH 5.9) Solvent solubi lity (g/1 00 mL at 20 °C) Chloroform 222 Acetone 144 n-Hexane 1.76 Methano l 49 .6 Xylene 63.9 Vapor pressure (25 °C) 1.4 x 10' 6 mmHg Dissociation constant ( PKa a t 25 

### ·q 3.7 Octanollwater partition coefficient 25 Log (K0 w) at 25 °C U

V

/v isible absorption spec trum (i n Not available methanol)

DP Barcode 0413698 / MRID No. 489981-0 I Page 4 of 12**,a,J** Triflumizol e / 12 8879 I CH EMTURA / 400**~ ~**  DA CO 7.4. 1 17.4.2 / 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 Tri a l
- Greenho use Cucumb er 

### B. EXPERIMENTAL DESIGN B.l. Study Site Info rmation

TABLE 8.1.1 . Trial S ite Co ndition s. Trial Identification (City, State/Year) Soil characteri stics Type % 0M2 pH CEC 3 TX 18 ( Weslaco , TX/2009 ) Not applicable ' Not No t Not applicabl e' app li cab le ' app l icable 1 FL42 (C itra, FL/2010 ) Not app licable 4 21.38 5.74 Not app li cable4 C 008 (Fort Col lin s, C0/2009) No t appl icab le 5 Not 5.510 6.5 Not aoolicable5 aoolicabl e 5 MD 13 (Sa lisbu ry, MD/2009) Not applicab le 6 Not Not Not applicable6 applicab le 6 applicab le 6 

### • Plants were grown m Su nshan e M1x # I(S unGr o Hom culture) (so1lless mcd1a). ln gre d1ents of the m1xture mc lu dc 70·80 Yo Canad ian sphagnum peat moss , perlite , dolomitic lim e s tone, gyps um , and a wetting a gent. Scotts Osmocote Plus ( 15-9-12 / 5-6 m o nths @ 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-Exc han ge Capacit y •rtants were grown in S p eed lin g® Scien tifica ll y Formu lated Peat-Lite Mix for Professional Gr owers (gr een h ouse container media) 1 Fafard Can adian G r owing Mix 2 (ge n eral purpose Canadian sphagnum peat mix) was used in the 5-gallon pots . This mix co ntained Canadian s phagnum pea t m oss, perlit e , vermi culi te , s tarter nutrients , a wettin g agent, and dol o mitic li meston e . 6 Pia nts were grown in rock wool. 

### Weather condition s at th e gree nhouses were gene ra ll y cons idered norm a L Plants were grown in a g ree nhouse-controll ed e nvironment. Common cu ltu ral practices were followed to maintain the crop. Additional main tenance pesticides and fertili zers we re used to produce co mmercial quality c ucu mbers ( greenhouse ) . At each test location , experimental plants were treated w ith five foliar directe d app li cat ions of triflumizo le, the act ive in gredi ent (42.14 %) 

### in Procure ® 480SC. All foliar applica tions tar geted a r ate of0.25 lb ai /A, a 7-day RT I, and a 0-day PHI , without the u se of a s ur fac ta nt. At the Co lorado greenhous e s i te, a decline trial was conducted with th e las t a ppli ca tion 0 , 3, 7, 12 and 1 5 days before harve s t (0
- 15 day PHI). The appli ca tion use patterns are s ummari ze d in Table 8 . 1.2.

DP Barcode 041 3698 I MRID No. 489981 -01 Pa ge 5 of 12Triflumizole / 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
TAB LE 8.1.2. Study Use Patte rn. Location (City, State/Year) TriaiiD

(Weslaco, TX/2009) TX 18

(Ci tra, FU2010) FIA2

(Fort Collins. C0 / 2009) C008

(Sa lisb ury , MD/2009) MDI3

- EP
- E nd-use Product 1 Gallo ns per Acre

· 'Rc-treatment Interval 'NA : Not app li cab l e EP 1

Procure® 480SC

Procure ® 480SC

Procure® 480SC

Procure® 480SC Method/Timing Foliar Directed/B looming and Fruiting Foliar Directed/Blooming and Fruiting Foliar Directed/Blooming and Fruiting Foliar Directed/Blooming and Fruiting Foliar Directed/B looming and Fruiting Foliar Directed / Fruiting Foliar Directe d/ Fruiting Foliar Directed/ Fruiting Foliar Directed / Fruiting Foliar Directed/ Fruiting Foliar Directed / Vegetative Foliar Directed/Imm ature fruit Foliar Dire cted / Immature fruit Foliar Directed/Imm ature fruit Foliar Directed/ Fruiting Foliar Directed/Firs t mature fruits Foliar Directed / Fruiting Foliar Directed /Fruiting Foliar Directed/Fruiting Foliar Directed / Matur e fruit Application Volume Rate RTI 3 To t a l Rate GPA2 Ib a i/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 10 0.9 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 Mi x/ Adjuvants

None

None

None

None

DP Barcode 041 3698 I M RID No. 489981-01 Page 6 of 12Tritlumizol el 128879 I CHEMTURA /400 DACO 7 .4.117.4 . 2 10PPTS 860.1500 10ECD 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 Geograph ical Locations

US E PA 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, fo ll owed by the treated plo t. Two untreated and two treated greenhouse cucumber samples were collected at all of the greenhouse tri als on the day of the l ast app li cation (0-day PHI) . All samples co ll ected at 0-day PH I 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 fru its were collected from each s ite depending on the variety. At the Co l orado 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 Co l orado field sit e, after stems and flowers were removed, cucumber fruits were quartered and/or hal ved lengthwise and/o r 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 trial s after samp li ng procedures were completed , greenhouse cucumber samples were
DP Barcode 0413698 I MRID No. 489981-01 Page 7 of 12Tritlumizole / 1288 79 I CHEMTURA /400

# ~·· DACO 7. 4.1 17 .4 .2 / 0PPTS 860 . 1500 / 0ECD II A 6.3 . 1 , 6.3.2, 6.3 .3 and IliA 8.3 . 1, 8.3 .2, 8.3.3 Crop F iel d Trial -Greenhouse Cucumber placed in labe l e d sample bags and held in froz en storage until shipment to the analytical laboratory . Treated greenhouse cucumber samples were placed in frozen storage within I hour and 32 minutes of samp li ng at th e Colorado site . All samples were shipped frozen to the a nalytical laboratory at the University of Californi a, Davis (UCD) by AC DS freezer truck or Overnight Air Express. Upon arrival the sam ples we re checked in and s tored frozen . Raw Agricultural Commodity (RAC) samples were processed w i th dry ice in a Hobart food chopper. Afte r the en ti re sample was chopped, a portion was p l aced in labeled g lass pint ja r s and surplus, if any, was put back into the sample bag and both were stored frozen (generally
- 20 °C). 

### B.3. Analytical Methodology Samp l es o f g reenhouse cucumber were analyzed using the method derived from "Determina t ion ofTriflumizole in Crops," Analytical Method #Meth-115, Revision # 3, Morse laborato r ies, Inc., July 18 , 2003. The study followed IR-4 Nat ional Pestic i de Clearance Laborato ry Phase Protocol PR# 09300 as a mend ed. Modifications made did not negative ly affect the performance of the method. Residues of trifl umizole and its aniline-containing metabolites were converted to F A-1-1 by ac idic a nd alkal in e reflux, followed b y distill ati on. The distillate was acidified followed by extraction with hex a ne. If necessary, further clean
- up was achieved by concentr atin g the hexane l ayers and using an optional si li ca solid phase extraction (SPE) procedure. Total triflumizo l e residues were quantitated using GC equip p ed with a MSD in SIM mode. All residues were converted to FA-1-1 and expressed i n parent equivalents . The analytical method was validated for triflumizole, FM-6-1, and FA-1-1 on greenhouse cucumber at three fo rtification 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 th e LLMV, the calculated LOD (standard deviation x o n e-tailed t- statis tic) and LOQ ( 3 x LOD) fo r FA-1- 1 on greenhouse cucumber we r e 0.015 ppm and 0.045 ppm , respectively. T he LLMV was 0.10 ppm. During the samp l e ana lysis, untreated greenhouse cucumber fruit were fortified with triflumizole at 0.1 ppm, 0.2 ppm , and 1 .0 ppm for concurrent recove ry spikes . Untreated greenhouse cucumber fruit were f ortified with FM-6
- 1 at 0.1 ppm and 1.0 ppm for concurrent recovery spikes. Greenhouse cucumber storage stab ili ty samples and concurrent recovery samples duri ng sample analysis were fortified with triflumizole, FM-6- 1 and FA-1-1 at 0.5 ppm. 

### C. RESULTS AND DISCUSSION The analytical me thod was adequate for residue data collection. Metho d validation recoveries of 

### triflumi zole , FM-6-1, and FA-1-1 in greenhouse cucumber samples fortified at 0. 1 , 1.0 , and 1 0.0 ppm averaged 76 ± 8% (n = 9) , 80 ± 8% (n = 9), and 74 ± 8% (n = 11), respec t ively. Concurrent
DP Barcode 0413698 I MRID No. 48998 1- 0 I Page 8 of 12

# uel•l Tritlumizolel 128879 I CHEMTURA 1 400 ,., 

### ==. 

# I DACO 7.4.1/7.4 . 2/0PPTS 860.150010ECD IIA 6.3 . 1 , 6.3.2, 6.3 ..J and lilA 8 . 3.1, 8.3 . 2, 8 . 3.3 Crop Field Trial
- Greenhouse Cucumber 

### recove ries of triflumi zole and FM-6-1 fortified in greenhouse cucumber samples were 69 ± 5% (n 

### = 4) and 87 ± 13% (n = 

### 3), respecti vely. The resu lts are presented i n Tab l es 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 (Tab l e C.2 . 1 ). To support this sto rage interval, a concurrent freezer storage stability study was conducted using control samples of cucumber fortified separately with triflumizole, FM-6-1, and FA- 1 -1 each at 0 . 5 ppm . The fortified samp l es were stored under the same conditions (-20°C) as the fie l d trial samples . At the end of the analytical phase, the stored samples were analyzed i n triplica te along wi th a contro l samp l e and control samples freshly fortified with each analyte. Concurrent recovery samples had recoveries of 74% , 94%, and 79% for triflumizo l e, FM-6-1, and FA-1-1, respectiv ely . T he average recovery from the s tored samples (corrected for concurrent recoveries) was 69%, 77% and 39% for parent, FM-6-1, and FA
- 1-1, respectively; for a mean average co rrected recovery of 62% for all three analytes (Table C.2.2). These r ecoveries 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 res i due decline in the storage stability study exceeds 30%, corrections to the magnitude of the residue data ar e needed to avoid underestimating residue and tolerance leve l s. Because the method converts parent and all me tabolites to a common moiety, corrections for the i nd i vidual residues could no t be determined. Therefore, the average decline of 38% over 832 days (0 . 0457% / day decrease) was used to correct residue values according to th e equation Rc 

### = R u + 

### (1
- (0 . 000457 x 

### DAYS)), where 

### Rc is the corrected residue concentration, R u is the uncorrected residue concentration, and DAYS is the number o f days in storage. Following five broadcast foliar app lications of 4 lb ai/gal SC tri flumizole totaling 1.25 lb a i/ A, the combined residues (uncor rect ed for storage declines) were <0.10
- 0.27 ppm i nion 8 samples of cucumber harvested at a 0
- day PHI. T he average uncorrected residue was 0.17 p pm and the HAFT residue was 0.26 ppm. When corrected for potenti al decl i nes during storage, combined residues inion all 8 samp l es were <0 . 14
- 0.39 ppm, the average residue was 0.25 ppm, and the HAFT residue was 0.34 ppm. In the decline s tudy, total triflumizole residues were at or below the LLMV at all sampling intervals ; thus, no decline trend could be discerned. The detailed res i due results from the four greenhouse cucumber trials are presented in T ab l e C.3. T able C.4 presents a summary of the results .

TABLE C.l.l. S u mmary of Recove ri es ofT ri flumizole from Green h ouse Cucumber Matrix S p ike level Sa mpl e size Type of Recoveries Mean ± s td dev (mg/kg) (n) Recovery (%) (%) Triflumizole 0 . 1 3 MV 67 , 80 ,6 1 68 ± 8 I C R- 65 0.2 I CR 71 71 ± 0 Greenhouse 3 MV 77,85 , 78 Cucumber F ruit 1.0 CR 65 76± 8 I 10.0 3 MV 83 , 80, 70 78 ± 7 0 . 5 I SSCR3 74 74 ±0 'M ethod Validat iOn DP Barcode 0413698 I MRlD No. 489981-0 I Pa ge9o fl2Triflumizo le l 128879 I CHE M TURA 1400 DACO 7 .4.117.4.2/0PPTS 860.1500 10ECD IIA 6 . 3.1, 6.3.2, 6.3 . 3 and IliA 8 . 3 . 1, 8.3.2, 8.3 . 3 Crop Fie ld Trial
- Greenhouse Cucumbe r l Concurrent Recovery 'Storage Stabili ty Concur r ent Recovery TABLE C.1. 2. S ummary of Reco veries of FM
- 6-1 from Gree nhou se Cucu mber Matrix Spike level (mg/kg)

0 . 1 G

reen house 1.0 Cucumber Fruit 10 . 0 0.5 I Method Validation 2 C

oncurrent Recovery ' Storage Stability Concurren t Recovery Sample size (n) 3 I 3 I 3 I Type of Recoveries Recovery (%) FM-6-1 MV 1 65,80, 73 CR 1 94 MV 86, 84, 89 CR 72 MV 86,82, 71 SSCR3 94

TABLE C .1. 3. Summa ry o f Recoveries ofFA-1-1 from Greenhouse Cucumber Mat rix 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 8 1 , 7 8 ,79 C ucumber Fruit 10.0 3 MV 86,85 , 71 0.2 I SSCR3 79 Method Vahdat1on lThis Recovery was omitted from calculations since it was thou ght to be double fortified ' Storage Stability Concurrent Recovery

TABLE C.2 . 1. Sum mary of S torage Co ndi t ions For Gree nhous e 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 I nterval of Demonstrated (RAC or extract) (°C) Actual Storage Duration ' (days) Storage Stabilit/ (days) Greenhouse C ucumber

- 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 fo r tification to extraction 517
- 881 517
- 881 517
- 881

TABLE C.2.2. Sta bili ty of T riflumizo le in Greenhouse Cucumb er 832 832 832

An alyte Spike Storage Freshly Fortified Stored Sample Average Corrected Level interval Recovery ' (%) Recoveries(%) [Avg] Stored Recover/(%) (ppm) (days) Trifl u mizole 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 Fres hly fortafied concurrent recovery reported as part of the storage stabtltty study (SSCR value) . 2 Average st ored sample recoveries were corrected fo r storage stability concurrent recovery (SSCR) va l ues .

DP Barcode 0413698 I MRID No. 489981-01 Mean Avg. Corrected Recovery(%) 62

Page 10 of 12Triflumizole / 128879 / CHEMTURA /400 DA CO 7.4.117.4.2/0PPTS 860.1500/0ECD II A 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 C.3. Residue Data from Gr eenhou se C ucumb e r F i e ld T rial s with Triflumi zo le T ria l iD Total Rate Storage PHI Re s idues (ppm) 1 (City, State ; Year) Zone Crop/ Variety (lb ai / A) (days) (days) Corrected for storage Uncorrected (Av g ] 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] Di va 09300.09
- FL 42 Greenhouse (Citra, FU2010) 3 cucumber / 1.259 517 0 0 .2 7 , 0.25 l0 . 26] 0.35, 0.33 [0 .3 4) J awe ll 0 0.10, < 0.10 [0.10] 0.14, <0. 1 4 [ 0.14] 09300.09-CO 08 Greenhouse 3 <0. 1 0, 0. 1 1 [0 . 1 1) <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. 1 4] 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 1 3 Greenhouse (Sa li sbury, 2 cucu mber / 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 m01et y, FA-1-1, wh1ch IS expressed as tnflum1zole eqUivalents . The s tatistically calculated LOQ and LOD we re 0.045 and 0.015 ppm , respectively; the LLMV was 0. 1 0 ppm. 2 As the method convert s parent and a ll metabolites to FA-1-1 and the average corrected recovery ofeach analyte varied (39-

77%), the average decline (38% ( 100%
- mean avg corrected %recovery) over 832 day s) was u se d to correct residues. Residue va l ues were corrected based on th e actual storage duration of each samples and assuming a decline of0.0457%/day of storage according to the equation R c = Ru + (I
- (0.000457 x DAYS)) , where Rc is the corrected r es idue concentration, Ru i s the uncorrected residue concentration, and OA YS is the number of days in storage.
TABLE C.4. S umm a r y of Resid u e D ata from G r ee nh o u se C ucumber Field Tria ls wit h Triflumizo le 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 Cuc umber Corrected Re s ults 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 samp le s- 2 x number of held tnals.

DP B arcod e D413698 I M RJD No . 489981-01 Page I I of 12Triflumizolel 128879 I CHEMTURA 1 400 DACO 7.4.1 17 .4 . 2 1 0PPTS 860.1500 1 0ECD liA 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 

### D. CONCLUSION The greenhouse cucumber field trials are adequate wi th res p ect to the residue chem istry guidelines (860.1500) and an EPA!HED ChemSAC dec ision regarding the number of trials. The field trials support the use of tri flumizole 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 RT I, and a 0-day PH I. Triflumizole residues in cucumber, corrected for decline in frozen storage, were 0.39 ppm or less when an SC formulation was app li ed acco rding to the supported use pattern. No residue decl i ne trend could be discerned as res i du es were at o r below the LLM V at all sampli ng interval s i n the residue decline trial. 

### E . REFERENCES DEB # 6410, 

### 1.0. No. 400-UGA, Tr iflumizole , Registration of A815 Technical , J. 

### Smith, 1992 

### F. D OCUMENT TRACKING Petition Number: 2E8119 DP Barcode: 0413698 PC Code: 128879 Te mplate Version June 2005 .

DP Barco de 0 413698 I MR ID No. 489981-01 Page 1 2 of 12