Fenpyroximate Summary of Analytical Chemistry and Residue Data DP# 405715

Page 1 of 16 **U.S. ENVIRONMENTA**  **L PROTECTION AG**  **ENCY**

**WA SHINGTON, D.C. 20460**  **OFFICE OF CHEMICAL SAFETY AND**  **POLLUTION PREVENTION MEMORANDUM**  **Date:** 08 - MAY - 201 3 **SUBJECT: Fenpyroximate**  . Peti tion for the Establishment of Permanent Tolerances for

Residues in/on Stone Fruits (Group 12 - 12), Tuberous and Corm Vegetables (Subgroup 1C), and Small Vine Climbing Fruits Except Kiwifruit (Subgroup 13 - 07F) . **Summary of Analytical Che mistry and Residue Data**  . **PC Code:** 129131 **DP Barcode:** D 4 05 7 1 5 **Decision No.:** 4 686 35 **Registration No s**  **. :**  71711 - 19 , 71711 - 4 **Petition No.:** 2 E8 0 72 **Regulatory Action:** Sec. 3 Registration **Risk Assessment Type:** NA **Case No.:** 7432 **T XR No.:**  NA **CAS No.:** 134098 - 61 - 6 (E - isomer) **MRID No s**  **.:** 48 9037 - 01 thru - 0 4 **40 CFR:** § 180. 566 **FROM:** George F. Kramer, Ph.D., Senior Chemist

Risk Assessment Branch 1 (RAB1) Health Effects Division (HED ; 7509P ) **THROUGH:** Dana M. Vogel, Acting Branch Chief, RAB1

Associate Division Director, HED (7509P) **TO:** Barbara Madden/ Sidney Jackson , RM 05 Registration Division (RD; 7505P) **Executive Summary** Fenp yroximate is a contact insecticide/miticide used for the control of leafhoppers, meal ybugs, and mites. Fenp yroximate is a mitochondrial electron - transport inhibitor (METI) which acts by targeting proton - translocating NADH:Q oxidoreductase and blocking ubiquinone reduction. The Interregional Project No. 4 ( IR- 4) has proposed a Section 3 Registration for application of fenp yroximate to stone fruits (group 12 - 12) , small vine climbing fruits except kiwifruit (subgroup 13 - 07F) , and tuberous and corm vegetables (subgroup 1C) . IR- 4, on behalf of the Agricultural Experiment Stations of C A , M I , M T , P A , TX , and U T , requests the establishment of tolerances for the for the combined residues of the insecticide fenp yroximate, including its metabolites and degradates, in or on the commodities in the table below. Compliance with the tolerance levels specified below is to be determined by measuring only

the sum of fenp yroximate, (

E) - 1,1 - dimethylethyl 4 - [[[[(1,3 - dimethyl - 5 -phenoxy- 1 H -py razol - 4 - yl ) methylene] amino]oxy]methyl] benzoate and its Z-isomer, (Z ) - 1,1 - dimethyl ethyl 4 - [[[[(1,3 -Fenpyroximate Summary of Analytical Chemistry and Residue Data DP# 405715

Page 2 of 16 dimethyl - 5 - phenoxy- l

H - py razol - 4 - yl ) methyl ene]amino]ox y] methyl]benzoate, calculated as the stoichiometric equivalent of fenp yroximate , in/on the following raw agricultural commodities (RACs): **Comm odity**  **Proposed Tolerance (ppm)**

Fruit, stone, group 12 2. 0 Vegetable, tuberous and corm, subgroup lC 0. 10 Fruit, small, vine climbing, except fuzzy kiwifruit, subgroup 13 - 07F 1.0 No new residue data were submitted to support tolerance on small vine climbing fruits except kiwifruit (subgroup 13 - 07F) . IR- 4 has requested that the established tolerance for residues in/on grape be expanded to its respective crop group. Fenp yroximate tolerances have been established in 40 CFR §180.566. Tolerances for plant commodities are expressed in terms of combined residues of fenp yroximate and its Z - isomer. Permanent tolerances for plant commodities, under §180.566(a)(1) range from 0.10 ppm for cotton undelinted seed to 2 0 ppm tea . Tolerances for milk and the fat, meat, and meat by products (excluding liver and kidney) of cattle, goat, horse, and sheep are listed in 40 CFR §180.566(a)(2) and are expressed in terms of the combined re sidues of fenpy roximate and its metabolites (

E) - 4 - [(1,3 - dimethyl - 5 -phenoxy py razol - 4 - yl ) - methylene aminooxy methyl]benzoic acid and ( E) - 1,1 - dimethylethyl - 2 - hydroxyethyl4 - [[[[(1,3 - dimethyl - 5 -phenoxy- 1 H - py razol - 4 - yl )methyl ene]amino]oxy]methyl]benzoate, calcul ated as the parent compound. Tolerances for cattle, goat, horse, and sheep liver and kidney are listed under 40 CFR §180.566(a)(3) at 0.25 ppm and are expressed in terms of fenp yroximate and its metabolite ( E) - 4 - [(1,3 - dimethyl - 5 - phenox yp yr azol - 4 - yl ) - methylene aminooxy methyl]benzoic acid, calculated as the parent compound . A time - limited tolerance for residues in/on honey at 0.10 ppm with a 12/31/13 expiration date is listed in 40 CFR §180.566(b) under a Section 18 Emergency Exemption. The nature of the residue in crops is understood based on acceptable plant metabolism studies with fenp yroximate on snap beans, apples, citrus, cotton, and grapes. The HED Metabolism Assessment Review Committee (MARC) has determined that the residues of concern for purposes of tolerance enforcement and risk assessment are the parent compound plus its Z isomer (M - 1). The nature of the residue in ruminants is adequatel y understood based on an acceptable metabolism study in goats. The MARC reviewed the se data and determined that the residues of concern for purposes of tolerance enforcement and risk assessment are parent, FenOH [( E) - 1,1 - dimethylethyl - 2 - hydroxyethyl4 - [[[[(1,3 - dimethyl - 5 - phenoxy- 1 H -py razol - 4 - yl )methyl ene]amino]oxy]methyl]benzoate], and M 3 [( E ) - 4 - [(1,3 - dimethyl - 5 -phenox yp yr azol - 4 - yl ) - methylene aminooxymethyl]benzoic acid] in milk, meat, and fat; and parent and M3 in liver and kidney . An adequate enforcement method is available for determination of fenp yroximate residues of concern in the proposed/registered crops. A gas chromatography method with nitrogen/phosphorus detection (GC/NPD), Method S19, has passed an Agency validation (DP# 269410, 10/10/00, G. Kramer). Method S19 has a limit of quantitation (LOQ) of 0.05 ppm for the combined residues of fenpy roximate and M - 1 in snap beans and avocados. A data - gathering liquid chromatography/mass spectroscop y/mass spectroscop y ( LC /MS/MS) method is also available. This method was used for the anal ys is of the samples from submitted field and pro cessing studies.Fenpyroximate Summary of Analytical Chemistry and Residue Data DP# 405715

Page 3 of 16 Data pertaining to multiresidue methods testing were previously submitted in conjunction with a petition for fenp yroximate tolerances in/on imported wine grapes and hops (PP#5E04435). Fenp yroximate was not adequatel y recovered b y any multiresidue protocol. No new livestock feeding studies were submitted with this petition. The only cattle feed commodities associated with this petition are potato culls and processed waste. The additional fenp yroximate uses are not expected to result in an increase in the maximum reasonabl y balanced diets (MRBDs). The existing tolerances on ruminant commodities are thus adequate to support registration of the proposed new uses of fenpy roximate. There are no swine or poultry feedstuffs associated with this petition. The submitted field trial residue data for stone fruit and potatoes are adequate. The field trial data reflect the proposed use pattern; an adequate number of trials were conducted in the appropriate geographic regions; and samples were anal yz ed for the residue of concern using validated data - collection methods. The storage intervals were also validated. Using the Organization for Economic Co - operation and Development (OECD) tolerance calculation procedures for the residue data sets indicate that the req uested tolerance levels are appropriate. However, a revised Section F with corrected commodity definitions is requested (see below). The submitted plum and potato processing studies are also adequate. Separate tolerances are not required for residues in/on any of the processed fractions. An adequate confined rotational crop study is available. [ 14 C]Fenpyroximate was applied to sandy loam soil at 0.20 lb ai/A (1X the maximum seasonal rate to annual crops addressed in this petition). Crops of radish, lettuce, and wheat were planted at 30, 120, and 365 days after treatment. Residues were too low to allow for metabolite identification. A field rotational crop study and rotational crop tolerances will, therefore, not be needed to support the proposed and registered uses. The proposed 30 - day plant - back interval (PBI) is appropriate. Codex and Mexican maximum residue limits (MRLs) are established for residues of fenp yroximate per se in/ grap es (fresh and dried) . Harmonization with the Codex and Mexican MRL s is not possible because the U.S. tolerance expression includes an additional isomer and the U.S. use pattern requires a higher numerical value . There are currently no established Canadian MRL s. A human - health risk assessment is forthcoming in a separate document ( D 404839 ). **Residue Chemistry Deficiencies** 860.1550 Proposed Tolerances A summary

of the recommended tolerance levels along with recommendations for commodity definitions are presented in Table 9 . The petitioner is required to submit a revised Section F to reflect the recommendations in Table 9 . **Background** The chemical structure and nomenclature of fenpy roximate and its Z - isomer and the physicochemical properties of fenpy roximate are presented in Tables 1 and 2.Fenpyroximate Summary of Analytical Chemistry and Residue Data DP# 405715

Page 4 of 16 **Table 1. Fenpyroximate Nomenclature.** Chemical structure

Common name Fenpyroximate Company experimental name NNI - 850 IUPAC name tert- butyl(E) - alpha - (1,3 - dimethyl - 5 - phenoxypyrazol - 4 - yl methyleneamino - oxy) - p - toluate CAS name 1,1 - dimethylethyl 4 - [[[( E) - [(1,3 - dimethyl - 5 - phenoxy1 H - py razol - 4 - yl)methylene] - amino]oxy]methyl]benzoate CAS registry number 134098 - 61 - 6 (E isomer); 111812 - 58 - 9 (unspecified stereochemistry) End -use product (EP) FujiMite ® 0.4 lb ai/gal EC formulation (5% ai; EPA Reg. No. 71711 - 19) Chemical structure of fenpyroximate Z - isomer metabolite 1,1 - dimethylethyl 4 - [[[(Z ) - [(1,3 - dimethyl - 5 - phenoxy1 H - py razol - 4 - yl)methylene] - amino]oxy]methyl]benzoate Metabolite M1 **Table 2. Physicochemical Properties of Fenpyroxim**  **ate.** Parameter Value Reference Melting range 99.3 - 101.7 ° C D301316, 5/3/04, L. Kutney pH 5.63 - 6.10 D301316, 5/3/04, L. Kutney Density 1.247 - 1.257 g/mL at 20 ° C D301316, 5/3/04, L. Kutney Water solubility Water, pH 5 - 21.4 ppb Water, pH 7 - 23.1 ppb Water, pH 9 - 29.8 ppb D257640, 8/20/99, G. Kramer Solvent solubility Acetone 15.0 g/100 mL Chloroform 119.7 g/100 mL DMSO 2.86 g/100 mL Ethanol 1.65 g/100 mL Ethyl acetate 20.1 g/100 mL Hexane 0.35 g/100 mL Methanol 1.53 g/100 mL Methylene chloride 130.7 g/100 mL Tetrahydrofuran 73.7 g/100 mL Toluene 26.8 g/100 mL Xylene 19.3 g/100 mL D301316, 5/3/04, L. Kutney

Vapor pressure 5.6 x 10 - 8 Pa at 25 ° C D257640, 8/20/99, G. Kramer Dissociation constant, pKa Not applicable; nearly insoluble in water D301316, 5/3/04, L. Kutney Octanol/water partition coefficient, Log(KOW) log P ow = 5.01 (PAI) D301316, 5/3/04, L. Kutney **860.1200 Directions for Use** The end - use products associated with this registration action are Fujimite ® 5EC Miticide/Insecticide (EPA Reg. No. 71711 - 19), an EC formulation containing 5% ai (equivalent to 0.4 lb ai/gal); Portal ® Miticide/Insecticide (EPA Reg. No. 71711 - 1 9), an EC formulation containing 5% ai (equivalent to 0.4 lb ai/gal); and Akari ® 5SC Miticide/Insecticide (EPA Reg. No. 71711 - 4), an SC formulation containing 5% ai (equivalent to 0.42 lb ai/gal). O C H 2 N N C H 3 C H 3 C N

O C O O C ( C H 3 ) 3 H

C O O C ( C H 3 ) 3 H

N N C H 3 C H 3 C N

O O C H 2Fenpyroximate Summary of Analytical Chemistry and Residue Data DP# 405715

Page 5 of 16 Summaries of the proposed end - use products and crop use patterns are presented in Tables 3a and 3b , respectivel y. **Table 3a**  **. Summary of Proposed End**  **- Use Product**  **.** Trade Name EPA

Reg. No. ai (% of formulation) Formulation Type Target Crops Target Pests Label Date Fujimite ® 5EC Miticide/ Insecticide 71711 - 19 5% (equivalent to 0.4 lb ai/gal) Emulsifiable

Concentrate stone fruits (group 12 -

12), small vine climbing fruits except kiwifruit (subgroup 13 - 07F), and tuberous and corm vegetables (subgroup 1C) Mites Undated draft label Portal ® Miticide/ Insecticide Akari ® 5SC Miticide/ Insecticide 71711 - 4 5% (equivalent to 0.42 lb ai/gal) Soluble

Concentrate stone fruits (group 12 -

12), and tuberous and corm vegetables (subgroup 1C) **Table 3b**  **. Summary of Proposed Directions for Use of Fenpyroximate.** Trade Name App.

Equipment App.

Rate (lb ai/A) Max. Seasonal

App. Rate (lb ai/A) PHI 1

(days) Max. #

App. Min.

GP A2 RTI 3

(days) Small Vine Climbing Fruits Except Kiwifruit (Subgroup 13 - 07F) FujiMite ® 5EC Portal ® Airblast 0. 05 0. 1 1 4 2 5 0 14 Stone Fruits (Group 12 - 12) FujiMite ® 5EC Portal ® Akari ® 5SC Airblast 0.1 0.2 7 2 8 0 14 Tuberous and Corm Vegetables (Subgroup 1C) FujiMite ® 5EC Portal ® Akari ® 5SC Groundboom,

Aerial 0.1 0.2 7 2 Ground: 2 0 Air: 5 7

1 PHI = pre - harvest interval. 2 GP A = gallons of water per acre. 3 RTI = retreatment interval. The following rotational crop restriction appears on the proposed label s : “Do not plant rotational crops other than those listed on the label for 30 days following the last application of this product.” Conclusions : The proposed use patterns are adequate to allow evaluation of the residue data submitted in support of this petition. **860.1300 Nature of the Residue -**  **Plants** The nature of the residue in crops is understood based on acceptable plant metabolism studies with fenp yroximate on snap beans, apple s , citrus, cotton, and grape s . The HED MARC has determined (D P# 292 639, J. Stokes , 7/12/03 ) that the residues of concern for purposes of tolerance enforcement and risk assessment are the parent compound plus its Z - isomer (M - 1).Fenpyroximate Summary of Analytical Chemistry and Residue Data DP# 405715

Page 6 of 16 **860.1300 Nature of the Res idue**  **- Livestock**  The nature of the residue in ruminants is adequately understood based on an acceptable metabolism study

in goats. The MARC reviewed these data and determined that the residues of concern for purposes of tolerance enforcement and risk ass essment are parent, Fen - OH, and M3 in milk, meat , and fat; and parent and M3 in liver and kidney (D P# 292639, J. Stokes, 7/12/03). Data concerning the nature of the residue in poultry have not been submitted. **860.1340 Residue Analytical Methods Plant Commodities**  Enforcement Analytical Method : Based on validation in a wide variety of matrices, an acceptable enforcement method, GC/NPD method DFG S19, is available for the proposed/registered crops . This method has undergone a petition method validation (D P# 269410, 10/10/00, G. Kramer) and is listed in the U.S. EPA Index of Residue Anal ytical Methods under fenp yroximate, Method ID 2000_109M, “Quantitation of Fenpy roximate Residues in Raw Agricultural and Processed Commodities.” All of the deficiencies pertaining to this method have been resolved (DP# 364908 , G. Kramer , 7/7/09 ) . Based on the lowest level s of method validation (LLMV s ) reported in various matrices, Method DFG S19 has a LOQ of 0.02 - 0. 1 0 ppm for the combined residues of fenpy roximate and M - 1 . Data - collection methods : Samples from the submitted field and processing studies were anal yz ed using an LC /MS/MS method adapted from a PTRLWest, Inc. method entitled “Magnitude of Residue of Fenp yroximate in/on Cotton Raw Agricultural Commodities and Processed Fractions of Cotton RACs” (PTRLStudy Nos. P819W and P820W). A number of minor modifications to the method were specified in the working methods (Working Outline WO 9.150 for peach and plum and 9.151 for cherry), including changes in clean - up procedures, reagents, and sampl e sizes. Briefl y, residues were extracted with acetone/water (4/1, v/v). The volume of the final extract was adjusted to be within the calibration range for instrumental anal ys is. Fenpy roximate and M 1 were determined b y LC /MS/MS. The L OQ (determined as the LLMV) was 0.05 ppm for fenp yroximate and M - 1 for each matrix. The method was adequate for data collection based on acceptable method validation and concurrent recovery data. Recoveries were within the acceptable range of 70 - 120%. The fortificati on levels used in method validation and concurrent method recovery

were adequate to bracket expected residue levels. Apparent residues of fenp yroximate and M - 1 were below the LOQ in/on all samples of untreated samples . Concurrent recoveries and residues in the treated samples were not corrected for residues in controls. Conclusions : The available enforcement analy tical method is adequate to enforce the proposed tolerance s . An acceptable data - collection method was used in the submitted field trial studies. **860.1360 Multiresidue Methods** Data pertaining to multiresidue methods testing were previously submitted in conjunction with a petition for fenp yroximate tolerances on imported wine grapes and hops (PP#5E04435; DP# 292394, 8/20/03, G. Kramer). Fenp yroximate was not adequatel y recovered by any multiresidueFenpyroximate Summary of Analytical Chemistry and Residue Data DP# 405715

Page 7 of 16 protocol. No further data are required. **860.1380 Storage Stability** IR- 4 conducted concurre nt storage stability studies with the potato , cherry , peach, and plum field trials. Inaddition, f

reezer storage stability

data are available for five diverse crops (i.e., vegetable s - 364 - 529 days in/on melon, pepper, and tomato ; a high - oil - content crop - 397 day s in avocado ; a leafy crop - 2 years in/on hops; a nut - 281 days in/on almond nutmeat and hulls; and a legume bean with pod - 560 days in/on snap beans) which demonstrate stability fenpy roximate residues (DP# 391843 , 5 / 11 / 12 , G. Kramer) . Conclusions : The available storage stability data for fenp yroximate are adequate to support the storage conditions and durations of samples from the submitted crop field trials processing studies. There are no storage stability issues and no corrections for storage stability need be applied to the field trial and processing study data . **860.1480 Meat, Milk, Poultry, and Eggs Ruminants:**  No new livestock feeding studies were submitted with this petition. The cattle feed commodities associated with this petition are potato culls and processed waste . Previously ( DP# 391843 , 5 / 11 / 12 , G. Kramer), the MRBD of fenpy roximate to beef and dairy cattle was estimated to be 0.76 - 1. 6 ppm, based on a diet consisting of corn RACs and cotton seed meal . A s the combined residues of fenpy roximate and M - 1 were <0.10 ppm in/on potato tubers in the crop field trials, the addition of potato feed items would not significantl y affect the MRDBs . **Hog and**  **Poultry :**  There are no swine or poultry feedstuff s associated with this petition . **860.1500 Crop Field Trials** Stone Fruit 48903701 .der.doc x (also includes 4890370 2 and 4890370 3) IR- 4 has submitted field trial data for fenp yroximate on stone fruit . Twenty - two field trials were conducted on stone fruit in the U.S. during the 2010 growing season. Seven cherry field trials ( 3 tart cherry

trials and 4 sweet cherry trials) were conducted in North American Fre e Trade Agreement (NAFTA) Growing Zones 1 (NY; 1 trial), 5 (MI; 2 trials), 9 (CO; 1 trial), 10 (CA; 1 trial), and 11 (WA; 2 trials), nine peach field trials were conducted in NAFTA Growing Zones 2 (NJ and NC; 3 trials), 4 (AR; 1 trial), 5 (MI ; 1 trial), 6 (TX; 1 trial), and 10 (CA; 3 trials), and six plum field trials were conducted in NAFTA Growing Zones 5 (MI; 1 trial), 10 (CA; 4 trials), and 12 (OR; 1 trial). Each trial consisted of one untreated plot and one to three treated plots. At each trial loc ation, one treated plot received two foliar- directed applications of FujiMite ® 5EC at 0.095 - 0.106 lb ai/A/application, for a total seasonal rate of 0.194 - 0.206 lb ai/A (1X) . Applications were generall y made at 13 - to 15 - day RTIs using ground equipment in spray volumes of 60 - 148 gal/A; applications at the CA95 peach trial were made at a 7 - day RTI. For all sites, a nonionicFenpyroximate Summary of Analytical Chemistry and Residue Data DP# 405715

Page 8 of 16 surfactant (NIS) was added to the spray mixture for each of the applications on treatment plot 2, except for two cherry

trials in which a crop - oil concentrate/organosilicone surfactant (COC/OSS) blend was used. Additional side - by- side plots were also established at two cherry trial sites (CA90 and WA22) and three peach trial sites (CA94, CA95, and NC18), in which a COC or OSS adjuvant was added to the spray mixture for treatment plot 3 and no adjuvant was added to the spray mixture for treatment plot 4. At the CA95 “no adjuvant” plot, the sprayer lost pre ssure and the second application was not completed; samples were not collected from this plot. Samples of cherries, peaches, and plums were harvested from all trials at a 6 - to 8 - day PHI ; additional samples of peaches were collected at PHIs of 2, 11, and 14 day s from one trial (CA95) to assess residue decline. For stone fruit harvested at a 6 - to 8 - day PHIfollowing two foliar- directed applications of FujiMite ® 5EC at 0.194 - 0.206 lb ai/A (with and without adjuvant), residues (and per- trial averages) of fenp yroximate, M - 1, and combined residues, respectivel y, were: 0.0889 - 0.897 (0.0934 - 0.807), <0.05 - 0.123 (<0.05 - 0.121), and <0.139 - 1.02 (<0.143 - 0.928) ppm in/on cherry ; 0.0589 - 0.200 (0.0594 - 0.195), <0.05 (<0.05), and <0.109 - <0.250 (<0.109 - <0.245) ppm in/on peach; and, <0.05 - 0.290 (<0.05 - 0.271), <0.05 (<0.05), and <0.10 - <0.340 (<0.10 - <0.321) ppm in/on plum (Table 4 ) . When the results following foliar applications are examined for the five side - by- side trial sites (three peach and two cherry), combined res idues of fenp yroximate and M - 1 were slightly higher following applications made with an adjuvant (NIS, OSS , or COC) than without an adjuvant by 1.1X to 1.6X, with the exception of one cherry side - by- side trial (WA22) in which the combined residues from the plot were 2.4X higher at the plot without an adjuvant than with an NI S adjuvant. For the four side - by- side trial s ites with both NI S and OSS plots, combined residues were slightly

higher for the OSS plots than the NIS plots (1.2X to 1.4X), with the excep tion of one peach side - by- side trial (CA95) in which the combined residues were 1.2X higher for the NI S plot than the OSS plot. For the one cherry trial with both NI S and COC plots, combined residues were higher for the COC plot by 2.7X. The submitted pe ach residue decline data indicate that mean residues of fenpy roximate and combined residues decrease with increasing PHI. Residues of M - 1 were all <L OQ (0.05 ppm) at each sampling interval; therefore, residue decline could not be assessed. **TABLE 4. Sum mary of Residue Data from** **Stone Fruit Trials with Fenpyroxim ate.**  Commodity Pl ot

Type Analyte Total Rate (lb ai/A) PHI

(days) Residue Levels (ppm) 1 n Sample Min. Sample Max. LAFT 2 HAFT 2 Median Mean Std. Dev. Cherry, Fruit Adjuvant Fenpyroximate 0.194 - 0.203 7 - 8 9 0.0889 0.8970 0.0934 0.807 0.358 0.450 0.239 M - 1 <0.05 0.1230 <0.05 0.1210 0.05 0.0685 0.0286 Combined <0.139 1.02 <0.143 0.928 0.408 0.519 0.266 No Adjuvant Fenpyroximate 0.201 7 2 0.269 0.313 0.273 0.299 0.286 0.286 NA

M - 1 <0.05 <0.05 <0.05 <0.05 0.05 0.05 NA Combined <0.319 <0.363 <0.323 <0.349 0.336 0.336 NA All Fenpyroximate 0.194 - 0.203 7 - 8 11 0.0889 0.897 0.0934 0.807 0.340 0.421 0.224 M - 1 <0.05 0.123 <0.05 0.121 0.05 0.065 0.027 Combined < 0.139 1.02 <0.143 0.928 0.390 0.486 0.249Fenpyroximate Summary of Analytical Chemistry and Residue Data DP# 405715

Page 9 of 16 **TABLE 4. Sum mary of Residue Data from** **Stone Fruit Trials with Fenpyroxim ate.**  Commodity Pl ot

Type Analyte Total Rate (lb ai/A) PHI

(days) Residue Levels (ppm) 1 n Sample Min. Sample Max. LAFT 2 HAFT 2 Median Mean Std. Dev. Peach, Fruit Adjuvant Fenpyroximate 0.195 - 0.206 6 - 8 12 0.0617 0.20 0.0731 0.195 0.122 0.125 0.0404 M - 1 <0.05 <0.05 <0.05 <0.05 0.05 0.05 NA Combined <0.112 <0.250 <0.123 <0.245 0.172 0.175 0.0404 No Adjuvant Fenpyroximate 0.201 - 0.202 6 - 8 2 0.0589 0.1002 0.0594 0.0978 0.0786 0.0786 NA M - 1 <0.05 <0.05 <0.05 <0.05 0.05 0.05 NA Combined <0.109 <0.150 <0.109 <0.148 <0.129 0.129 NA All Fenpyroximate 0.195 - 0.206 6 - 8 14 0.0589 0.20 0.0594 0.195 0.110 0.118 0.0415 M - 1 <0.05 <0.05 <0.05 <0.05 0.05 0.05 NA Combined <0.109 <0.250 <0.109 <0.245 0.160 0.168 0.0415 Plum, Fruit Adjuvant Fenpyroximate 0.198 - 0.206 6 - 7 6 <0.05 0.290 <0.05 0.271 0.106 0.130 0.0884 M - 1 <0.05 <0.05 <0.05 < 0.05 0.05 0.05 N/A Combined <0.10 <0.340 <0.10 <0.321 0.157 0.180 0.0883 1 Except for sample min/max, values reflect per- trial averages; n = no. of field trials. N/A = not applicable. 2 LAF T = lowest - average field trial; HAFT = highest - average field trial. Conclusions : The submitted residue data are adequate to fulfill data requirements for stone fruit . The number and locations of the crop field trials are in accordance with OPPTS Guideline 860.1500 (Table 5 ). The available data will support the proposed use pattern. **TABLE 5**  **. Trial Numbers and Geographical Locations**  . NAFTA Gro wing Zones Cherry Peach Plum

Submitted Requested 1 Submitted Requested 1 Submitted Requested 1

Canada U.S. Canada U.S. Canada U.S. Sweet Tart Sweet Tart 1 -- 1 -- -- 1/1 -- -- 1/1 -- -- -- 2 -- -- -- -- -- 3 2

-- 4/3 -- -- -- 4 -- -- -- -- -- 1 -- 1/0 -- -- -- 5 1 1 2

-- 2/2 5/4 1 -- 1/1 1 -- 1/1 6 -- -- -- -- -- 1 -- 1/1 -- -- -- 9 -- 1 -- -- 1/1 -- -- -- -- -- -- 10 1 -- -- 2/2 -- 3 -- 4/3 4 -- 5/4 11 2 -- -- 3/2 1 3 /0 -- -- -- -- -- 1/0 12 -- -- -- 1/0 1 3 /0 -- -- -- 1 -- 1/1 Total 4 3 2

-- 8/6 8/6 9 2

-- 12/9 6 -- 8/6 1 As per OCSPP 860.1500, Tables 2 and 5 for cherry, peach and plum as the representative crops of stone fruits group 12. The second number reflects a 25% reduction in the number of trials allowed for the crop as a representative commodity in support of a crop group/subgroup tolerance or when application results in no quantifiable residues. For a stone fruit crop group tolerance, only **six trials of sweet or tart cherries are required** . 2 HED has concluded that two sweet cherry trials conducted in MI (MI24 and MI25) and two peach trials conducted in NJ (NJ09 and NJ10) each constitute a single trial with replicate samples for purposes of 860.1500 data requirements. 3 Trial can be conduc ted in either Zone. The residue data for stone fruit were analyzed using the OECD tolerance calculation procedures (see Appendix I). When the results for the five side - by- side trial sites (NI S, OSS or COC ) were entered into the spreadsheet , the plot with the highest residue was chosen. The recommended tolerance s for the combined residues of fenp yroximate and M - 1 are 2.0 ppm in/on cherry , 0.60 ppm in/on peach , and 0.60 ppm in/on plum . The appropriate tolerance for the combined residues of fenpy roximate and M - 1 in/on fruit, stone, group 12 is thus 2.0 ppm .Fenpyroximate Summary of Analytical Chemistry and Residue Data DP# 405715

Page 10 of 16 Potato 48903704.der1 .doc x Twelve field trials were conducted in the U.S. during the 2009 - 2010 growing season in NAFTA Growing Zones 1 (NY; 2 trials), 2 (NC; 1 trial); 3 (FL; 1 trial); 5 (OH, MI , and WI ; 3 trials), 9 (NM; 1 trial), 10 (CA; 1 trial), and 11 (ID and WA; 3 trials). Each trial consisted of one untreated plot and one treated plot. At each trial location, the treated plot received two foliar broadcast or directed applications of FujiMite ® 5EC at 0.098 - 0.112 lb ai/A/application, for a total seasonal rate of 0.198 - 0.215 lb ai/A (1X) . Applications were made at 6 - to 8 - day

RTIs using ground equipment in spray volumes of 21.4 - 50.3 gal/A. A NI S was added to the spray

mixture for each of the applications. Samples of potatoes were harvested from all trials at a 6 - to 7 - day PHI; additional samples of potatoes were collected at PHIs of 0, 3, 9 - 11, and 12 - 14 day s from two trials (09 -NC18 and 09 - MI 11) to assess residue decline. Following two foliar broadcast or directed applications of the 0.4 lb ai/gal EC formulation of fenp yroximate at 0.198 - 0.215 lb ai/A, residues of fenpy roximate, M - 1, and combined residues, respectivel y, in/on potato tubers harvested at a 6 - to 7 - day PHI were <0.05, <0.05, and <0.10 ppm (Table 6 ) . In the residue - decline trials, residues of fenp yroximate and M - 1 were <0.05 ppm in/on all samples. Therefore, residue decline could not be assessed. **TABLE 6**  **. Summary of Residue Data from Potato Field Trials with Fenpyroximate.**  Commodity Analyte Total Rate (lb ai/A) PHI

(days) Residue Levels (ppm) 1 n Sample Min. Sample Max. LAFT 2 HAFT 2 Median Mean Std. Dev. Potato, Tubers Fenpyroximate 0.198 - 0.215 6 - 7 12 <0.05 <0.05 <0.05 <0.05 0.05 0.05 N/A

M - 1 <0.05 <0.05 <0.05 <0.05 0.05 0.05 N/A Combined <0.10 <0.10 <0.10 <0.10 0.10 0.10 N/A 1 Except for sample min/max, values reflect per - trial averages; n = no. of field trials. N/A = not applicable. 2 LAF T = lowest - average field trial; HAFT = highest - average field trial. Conclusions : The submitted residue data are adequate to fulfill data requirements for potatoes as a representative of the v egetable, tuberous and corm, subgroup lC . The number and locations of the crop field trials are in accordance with OPPTS Guideline 860.1500 (Table 7 ). The available data will support the proposed use pattern. **TABLE 7**  **. Trial Numbers and Geographical Locations**  . NAFTA Growing Regions Potato Submitted Requested 1 Canada U.S. 1 2 -- 2/2 2 1 -- 1/1 3 1 -- 1/1 5 3 2

-- 4/2 9 1 -- 1/1 10 1 -- 1/1 11 3 2

-- 6/4 Total 12 16/12 1 As per OCSPP 860.1500, Table 5 for potato. The second number reflects a 25% reduction in the number of trials allowed when application results in no quantifiable residues.Fenpyroximate Summary of Analytical Chemistry and Residue Data DP# 405715

Page 11 of 16 2 HED has concluded that four sets of two trials conducted in WI (09 - WI12 and 09 - WI16), ID (09 - ID12 and 09 - ID13), and WA (09 - WA05 and 09 - WA06; 09 - WA* 07 and 09 - WA* 08) each constitute a single trial with replicate samples for purposes of 860.1500 data requirements. The residue data for potatoes were not anal yz ed using the OECD tolerance calculation procedures as all residues were <LOQ . The recommended tolerance for the combined residues of fenp yroximate and M - 1 is 0. 1 0 ppm for the v egetable, tuberous and corm, subgroup lC . Fruit, small, vine climbing, except fuzzy kiwifruit, subgroup 13 - 07F No additional field trial data were submitted. A tolerance for combined residues of fenp yroximate and M - 1 in/on grapes has been established at 1 .0 ppm [40 CFR §180.5 6 6]. IR- 4 has proposed to convert this tolerance to f ruit, small, vine climbing, except fuzzy kiwifruit, subgroup 13 - 07F tolerance at the same level. As the proposed use on f

ruit, small, vine climbing, except fuzzy kiwifruit, subgrou

p 13 - 07F is identical to the existing use grapes on the product labels for FujiMite ® 5EC , Portal ® , Akari ® 5SC , the existing grape tolerance can be translated to f ruit, small, vine climbing, except fuzzy kiwifruit, subgroup 13 - 07F . **860.1520 Processed Fo od and Feed**  Plum 48903703 .de r .doc x In one trial conducted in CA, plums received two foliar- directed applications of FujiMite ® 5EC at an exaggerated rate of 0.509 - 0.511 lb ai/A/application for a total seasonal rate of 1.02 lb ai/A (~5X) . Applications were made at a 13 - day RTI using ground equipment in spray volumes of 142 gal/A. A NIS was added to the spray mixture for each of the applications. Plums were harvested at a PHI of 7 days and processed into dried plums at the field site using simulated co mmercial procedures. Adequate descriptions were provided of the processing procedures; material balance summaries were not provided. Following two foliar broadcast applications of FujiMite ® 5EC at a total seasonal rate of 1.0 lb ai/A (~5X), average resid ues of fenp yroximate, M - 1, and combined residues, respectivel y were 1.84, 0.208, and 2.05 ppm in/on plums (RAC) and 3.18, 0.316, and 3.50 ppm in/on dried plums (Table 8 ) . The processing data indicate combined residues of fenp yroximate and M - 1 may concentr ate in dried plums (processing factor of 1.7X). The observed processing factors do not exceed the theoretical concentration factor of 3.4X for prunes (OCSPP 860.1520, Table 2, based on loss of water). **TABLE 8**  **. Residue Data from Plum Processing Study**  **with Fenpyroximate.** RAC Processed

Commodity Total

Rate (lb ai/A) PHI

(days) Residues (ppm) 1 Processing Factor2 Fenpyroximate M - 1 Combined Fenpyroximate M - 1 Combined Plum Fruit (RAC) 1.020 7 1.84 0.208 2.05 --- --- ---

Dried plum 3.18 0.316 3 3.50 1.7X 1.5X 1.7X 1 All values are the average of replicate analyses. The LOQ was 0.05 ppm for each analyte. 2 Processing f

actor = average residue in processed fraction ÷ average residue in unprocessed RAC commodity. 3 Mean of multiple analyses.Fenpyroximate Summary of Analytical Chemistry and Residue Data DP# 405715

Page 12 of 16 Conclusions: Concentration following processing was observed in dried plums . Multiplication of the p lum HAFT residue (0.321 ppm) b y the dried plum processing factor of 1.7X yi elds a value ( 0. 55 ppm) which is less than the recommended RAC tolerance ( 2 .0 ppm); therefore, a separate tolerance i s not required for dried plum s. Potato DER Reference List 48903704.der2.docx In one trial conducted in ID, potatoes received two foliar broadcast applications of FujiMite ® 5EC at an exaggerated rate of 0.505 - 0.507 lb ai/A/application for a total seasonal rate of 1.012 lb ai/A (5X). Applications were made at a 7 - day RTI using ground equipment in spray volumes of 45.4 - 45.7 gal/A. A NIS was added to the spray mixture for each of the applications. Potatoes were harvested at a PHI of 7 day s and processed into flakes, chips, and wet peel b y the Food Technology

Center (Caldwell, ID) using simulated commercial procedures. Adequate descriptions were provided of the processing pro cedures, including material balance summaries. Following two exaggerated - rate applications of fenpy roximate, average residues of fenp yroximate and M - 1 were below the LOQ (<0.05 ppm) in/on potato tubers (RAC), flakes, chips, and wet peel; therefore, proces sing factors could not be calculated. The theoretical concentration factors for potato are 4.7X for dried flakes/granules and 4.0X for processed waste (based on loss of water, OPPTS 860.1520, Table 2; and separation of components; OPPTS 860.1520, Table 3, respectively). Conclusions: These data indicate that significant concentration of fenp yroximate residues are unlikely to occur in the processed fractions of p otato ; therefore, separate tolerances are not required for potato processed fractions. **860.1650 Submittal of Analytical Reference Standards** Analy tical standards for fenpy

roximate (with expiration date of 11/20/2015 ) and its Z - isomer (with expiration date of 5/16/2014 ) are currentl y available in the EPA National Pesticide Standards Repository (personal communication with Theresa Cole , Anal ytical Chemistry Branch , 2/23/2012 ). **860.1850 Confined Accumulation in Rotational Crops 860.1900 Field Accumulation in Rotational Crops**  No new confined rotational crop data were submitted with this petition. An acceptable confined rotational crop study was previously submitted in support of the tolerance petition for uses on pome fruit s , cotton, and grapes (PP#s 0F06437 and 0E06519; DP#s 291925 and 29192 6, 8/20/03, G. Kramer; 45649913.der.wpd). In the study , lettuce, radish, and wheat were planted 30, 120, and 365 day s following treatment of sandy loam soil at 0.2 lb ai/A. The application rate used in the study

is 1X the proposed maximum seasonal rate to the crops addressed in this petition . The rotational crop data indicated that fenp yroximate - related residues were <0.01 ppm in all samples of rotated lettuce, radish, and wheat planted at 30 - , 120 - , and 365 - day PBI s exceptFenpyroximate Summary of Analytical Chemistry and Residue Data DP# 405715

Page 13 of 16 wheat straw from the 120 - day PBI. The proposed 30 - day PBI on the product labels is appropriate. **860.1550 Proposed Tolerances** IR- 4 has proposed a tolerance expression for the combined residues of the insecticide fenp yroximate, including its metabolites and degradates, in or on the commodities in the table below. Compliance with the tolerance levels specified below is to be determined by measuring only the sum of fenpy

roximate, (E) - 1,1 - dimethylethyl4 - [[[[(1,3 - dimethyl - 5 - phenox y- 1H py razol - 4 - yl ) methyl ene] amino]ox y] methyl] benzoate and its Z-isomer, (Z) - 1,1 - dimethylethyl4 - [[[[(1,3 - dimethyl - 5 - phenoxy- lH -py razol - 4 - yl ) methylene]amino]oxy] methyl]benzoate, calculated as the stoichiometric equivalent of fenpyroximate . Codex and Mexican MRLs are established for residues of fenp yroximate per se in/ grap es (f resh and dried) . Harmonization with the Codex and Mexican MRL s is not possible because the U.S. tolerance expression include s an additional isomer and the U.S. use pattern requires a higher numerical value . There are currentl y no e stablished Canadian MRL s. The submitted U.S. stone fruit residue data were entered into the tolerance spreadsheet as per the OECD tolerance calculation procedures in order to determine appropriate tolerance levels ; see Appendix I . The submitted residue d ata for potato were not entered into the tolerance spreadsheet because all treated samples bore combined residues below the LOQ of 0 . 1 0 ppm. A summary

of recommended tolerances for the current petition is listed in Table 9 . **A revised Section F specifying the HED**  **- recommended tolerances should be submitted.**  **Table 9**  **. Tolerance Summary for Fenpyroxim ate.**  Commodity Proposed Tolerance (ppm) HED - Recommended

Tolerance (ppm) Correct Commodity

Definition/Comments Fruit, stone, group 12 2.0 2.0 Fruit, stone, group 12 - 12 Vegetable, tuberous and corm, subgroup lC 0.10 0.10 Fruit, small, vine climbing, except fuzzy kiwifruit, subgroup 13 - 07F 1.0 1.0 **Rem ove from** **40 CFR §180.566 (a)(1):** Grape Attachments: International Residue Limit s sheet Appendix I - Tolerance - Assessment Calculations cc: G. Kramer (RAB1) RDI: RAB1 Chemists ( 12 / 12 / 12 ) G.F. Kramer: S10 957 :PY - S:(703)305 - 5079:7509P:RAB1 Template Version September 2005Fenpyroximate Summary of Analytical Chemistry and Residue Data DP# 405715

Page 14 of 16 

### International Residue Limits

**Fenpyroximate** 

### ( 129131 ; 12/03/2012 ) Summary of US and International Tolerances and Maximum Residue Limits Residue Definition : US Canada Mexico 2 Codex 3 40 CFR 180. 566 : (a) General. (1) Tolerances are established for combined residues of the insecticide fenpyroximate, (E) - 1,1 - dimethylethyl 4 - [[[[(1,3 - dimethyl - 5 -phenoxy - 1 H -py razol - 4 - yl) methylene] amino]oxy]methyl]benzoate and its Z - isomer, (Z) - 1,1 - dimethylethyl 4 - [[[[(1,3 - dimethyl - 5 -phenoxy - 1 H

-py razol - 4 - yl)methylene] ami no]oxy]methyl]benzoate None Fenpyroximate

Commodity 1 Tolerance (ppm) /Maximum Residue Limit (mg/kg) US Canada Mexico 2 Codex 3 Fruit, stone, group 12 2.0 Vegetable, tuberous and corm, subgroup 1C 0.10 Fruit, small, vine climbing, except fuzzy kiwifruit, subgroup 13 - 07F 1.0 0.1 grapes 0.3 dried grapes (=currants, raisins and sultanas) Completed: M. Negussie; 12/04/2012 1 Includes only commodities of interest for this action. Tolerance values should be the HED recommendations and not those proposed by the applicant. 2 Mexico adopts US tolerances and/or Codex MRLs for its export purposes. 3 * = absent at the limit of quantitation; Po = postharvest treatment, such as treatment of stored grains. PoP = processed postharvest treated commodity, such as processing of treated stored wheat . (fat) = to be measured on the fat portion of the sample . MRLs indicated as proposed have not been finalized by the CCPR and the CAC.Fenpyroximate Summary of Analytical Chemistry and Residue Data DP# 405715

Page 15 of 16 **APPENDIX I: Tolerance**  **- Assessment Calculations** 

**Fenpyroximate Cherry, Fruit**  **USA 0.194**  **- 0.203 lb ai/A, PHI = 7**  **- 8 d**  **Total number of data (n)** 7 **Percentage of censored data** 0% **Number of non -**  **censored data**  7 **Lowest residue** 0.312 **Highest residue** 0.928 **Median residue** 0.507 **Mean** 0.593 **Standard deviation (SD)** 0.246 **Correction factor for censoring (CF)** 1.000 **Proposed MRL estimate**

**- Highest residue**  0.928

**- Mean + 4 SD**  1.579

**- CF x 3 Mean**  1.780 **Unrounded MRL** 1.780 **Rounded MRL 2**  High uncertainty of MRL estimate. [Small dataset] Residues (mg/kg) n 0.312 1 0.39 1 0.408 1 0.507 1 0.786 1 0.823 1 0.928 1 **Fenpyroximate Peach, Fruit**  **USA 0.195**  **- 0.206 lb ai/A, PHI = 6**  **- 8 d**  **Total number of data (n)**  9 **Percentage of censored data** 0% **Number of non -**  **censored data** 9 **Lowest residue** 0.123 **Highest residue** 0.245 **Median residue** 0.164 **Mean** 0.174 **Standard deviation (SD)** 0.043 **Correction factor for censoring (CF)** 1.000 **Proposed MRL estimate** 

**- Highest residue**  0.245

**- Mean + 4 SD**  0.348Fenpyroximate Summary of Analytical Chemistry and Residue Data DP# 405715

Page 16 of 16 **- CF x 3 Mean**  0.523 **Unrounded MRL** 0.523 **Rounded MRL 0.6**  **Residues (mg/kg) n**  0.123 1 0.1249 1 0.1483 1 0.1556 1 0.1641 1 0.1795 1 0.1993 1 0.2303 1 0.2452 1 **Fenpyroximate Plum,**  **Fruit USA**  **0.198 -**  **0.206 lb ai/A, PHI = 6 -**  **7 d Total number of data (n)**  6 **Percentage of censored data** 33% **Number of non -**  **censored data** 4 **Lowest residue** 0.100 **Highest residue** 0.321 **Median residue** 0.157 **Mean** 0.180 **Standard deviation (SD)** 0.088 **Correction factor for censoring (CF)** 0.778 **Proposed MRL estimate**

**- Highest residue**  0.321

**- Mean + 4 SD**  0.533

**- CF x 3 Mean**  0.420 **Unrounded MRL** 0.533 **Rounded MRL 0.6**  High uncertainty of MRL estimate. [Small dataset] **Residues (mg/kg) n**  <0.1 2 0.134 1 0.179 1 0.245 1 0.321 1