
                        U.S. ENVIRONMENTAL PROTECTION AGENCY
                               WASHINGTON, D.C.  20460
                                       
		OFFICE OF
		CHEMICAL SAFETY AND
		POLLUTION PREVENTION


MEMORANDUM

Date:		08-MAY-2013

SUBJECT:	Fenpyroximate.  Petition 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 Chemistry and Residue Data.

PC Code:  129131
DP Barcode:  D405715
Decision No.:  468635
Registration Nos.:  71711-19, 71711-4
Petition No.:  2E8072
Regulatory Action:  Sec. 3 Registration
Risk Assessment Type:  NA
Case No.:  7432
TXR No.:  NA
CAS No.:  134098-61-6 (E-isomer)
MRID Nos.:  489037-01 thru -04
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

Fenpyroximate is a contact insecticide/miticide used for the control of leafhoppers, mealybugs, and mites.  Fenpyroximate 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 fenpyroximate 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 CA, MI, MT, PA, TX, and UT, requests the establishment of tolerances for the for the combined residues of the insecticide fenpyroximate, 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 fenpyroximate, (E)-1,1-dimethylethyl 4-[[[[(1,3-dimethyl-5-phenoxy-1H-pyrazol-4-yl) methylene] amino]oxy]methyl] benzoate and its Z­isomer, (Z)-1,1-dimethylethyl 4-[[[[(1,3-dimethyl-5- phenoxy-lH-pyrazol-4-yl) methylene]amino]oxy] methyl]benzoate, calculated as the stoichiometric equivalent of fenpyroximate, in/on the following raw agricultural commodities (RACs):

                                   Commodity
                           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.

Fenpyroximate tolerances have been established in 40 CFR §180.566.  Tolerances for plant commodities are expressed in terms of combined residues of fenpyroximate and its Z-isomer.  Permanent tolerances for plant commodities, under §180.566(a)(1) range from 0.10 ppm for cotton undelinted seed to 20 ppm tea.  Tolerances for milk and the fat, meat, and meat byproducts (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 residues of fenpyroximate and its metabolites (E)-4-[(1,3-dimethyl-5-phenoxypyrazol-4-yl)-methylene aminooxymethyl]benzoic acid and (E)-1,1-dimethylethyl-2-hydroxyethyl 4-[[[[(1,3-dimethyl-5-phenoxy-1H-pyrazol-4-yl)methylene]amino]oxy]methyl]benzoate, calculated 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 fenpyroximate and its metabolite (E)-4-[(1,3-dimethyl-5-phenoxypyrazol-4-yl)-methylene aminooxymethyl]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 fenpyroximate 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 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 assessment are parent, Fen-OH [(E)-1,1-dimethylethyl-2-hydroxyethyl 4-[[[[(1,3-dimethyl-5-phenoxy-1H-pyrazol-4-yl)methylene]amino]oxy]methyl]benzoate], and M3 [(E)-4-[(1,3-dimethyl-5-phenoxypyrazol-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 fenpyroximate 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 fenpyroximate and M-1 in snap beans and avocados.  A data-gathering liquid chromatography/mass spectroscopy/mass spectroscopy (LC/MS/MS) method is also available.  This method was used for the analysis of the samples from submitted field and processing studies.  

Data pertaining to multiresidue methods testing were previously submitted in conjunction with a petition for fenpyroximate tolerances in/on imported wine grapes and hops (PP#5E04435).  Fenpyroximate was not adequately recovered by 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 fenpyroximate uses are not expected to result in an increase in the maximum reasonably balanced diets (MRBDs).  The existing tolerances on ruminant commodities are thus adequate to support registration of the proposed new uses of fenpyroximate.  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 analyzed 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 requested 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 fenpyroximate per se in/ grapes (fresh and dried).  Harmonization with the Codex and Mexican MRLs 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 MRLs.

A human-health risk assessment is forthcoming in a separate document (D404839).

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 fenpyroximate and its Z-isomer and the physicochemical properties of fenpyroximate are presented in Tables 1 and 2.
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-ylmethyleneamino-oxy)-p-toluate
CAS name
1,1-dimethylethyl 4-[[[(E)-[(1,3-dimethyl-5-phenoxy1H-pyrazol-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[(R)] 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-phenoxy1H-pyrazol-4-yl)methylene]-amino]oxy]methyl]benzoate
                                 Metabolite M1

Table 2.  Physicochemical Properties of Fenpyroximate.
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	21.4 ppb 
Water, pH 7-23.1 ppb 	23.1 ppb
Water, pH 9-29.8 ppb	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 Pow = 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[(R)] 5EC Miticide/Insecticide (EPA Reg. No. 71711-19), an EC formulation containing 5% ai (equivalent to 0.4 lb ai/gal); Portal[(R)] Miticide/Insecticide (EPA Reg. No. 71711-19), an EC formulation containing 5% ai (equivalent to 0.4 lb ai/gal); and Akari[(R)] 5SC Miticide/Insecticide (EPA Reg. No. 71711-4), an SC formulation containing 5% ai (equivalent to 0.42 lb ai/gal).

Summaries of the proposed end-use products and crop use patterns are presented in Tables 3a and 3b, respectively.

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[(R)] 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[(R)] Miticide/
                                  Insecticide
                                       
                                       
                                       
                                       
                                       
                                       
                            Akari[(R)] 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.
                                    GPA[2]
                                       
                                    RTI[3]
                                    (days)
         Small Vine Climbing Fruits Except Kiwifruit (Subgroup 13-07F)
                               FujiMite[(R)] 5EC
                                  Portal[(R)] 
                                   Airblast
                                     0.05
                                      0.1
                                      14
                                       2
                                      50
                                      14
                          Stone Fruits (Group 12-12)
                               FujiMite[(R)] 5EC
                                  Portal[(R)]
                                 Akari[(R)] 5SC
                                   Airblast
                                      0.1
                                      0.2
                                       7
                                       2
                                      80
                                      14
                  Tuberous and Corm Vegetables (Subgroup 1C)
                               FujiMite[(R)] 5EC
                                  Portal[(R)]
                                 Akari[(R)] 5SC
                              Groundboom, Aerial
                                      0.1
                                      0.2
                                       7
                                       2
                                  Ground: 20
                                    Air:  5
                                       7
[1]  PHI = pre-harvest interval.
[2]  GPA = gallons of water per acre.
[3]  RTI = retreatment interval.

The following rotational crop restriction appears on the proposed labels:  "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 fenpyroximate on snap beans, apples, citrus, cotton, and grapes.  The HED MARC has determined (DP# 292639, 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).  


860.1300 Nature of the Residue - 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 assessment are parent, Fen-OH, and M3 in milk, meat, and fat; and parent and M3 in liver and kidney (DP# 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 (DP# 269410, 10/10/00, G. Kramer) and is listed in the U.S. EPA Index of Residue Analytical Methods under fenpyroximate, Method ID 2000_109M, "Quantitation of Fenpyroximate 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 levels of method validation (LLMVs) reported in various matrices, Method DFG S19 has a LOQ of 0.02-0.10 ppm for the combined residues of fenpyroximate and M-1.  

Data-collection methods:  Samples from the submitted field and processing studies were analyzed using an LC/MS/MS method adapted from a PTRL West, Inc. method entitled "Magnitude of Residue of Fenpyroximate in/on Cotton Raw Agricultural Commodities and Processed Fractions of Cotton RACs" (PTRL Study 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 sample sizes.  

Briefly, 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 analysis.  Fenpyroximate and M-1 were determined by LC/MS/MS.  The LOQ (determined as the LLMV) was 0.05 ppm for fenpyroximate 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 fortification levels used in method validation and concurrent method recovery were adequate to bracket expected residue levels.  Apparent residues of fenpyroximate 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 analytical method is adequate to enforce the proposed tolerances.  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 fenpyroximate tolerances on imported wine grapes and hops (PP#5E04435; DP# 292394, 8/20/03, G. Kramer).  Fenpyroximate was not adequately recovered by any multiresidue protocol.  No further data are required.


860.1380 Storage Stability

IR-4 conducted concurrent storage stability studies with the potato, cherry, peach, and plum field trials.  In addition, freezer storage stability data are available for five diverse crops (i.e., vegetables- 364-529 days in/on melon, pepper, and tomato; a high-oil-content crop- 397 days 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 fenpyroximate residues (DP# 391843, 5/11/12, G. Kramer). 

Conclusions:  The available storage stability data for fenpyroximate 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 fenpyroximate 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.  As the combined residues of fenpyroximate and M-1 were <0.10 ppm in/on potato tubers in the crop field trials, the addition of potato feed items would not significantly affect the MRDBs.  

Hog and Poultry:  There are no swine or poultry feedstuffs associated with this petition.


860.1500 Crop Field Trials

Stone Fruit

48903701.der.docx (also includes 48903702 and 48903703)

IR-4 has submitted field trial data for fenpyroximate 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 Free 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 location, one treated plot received two foliar-directed applications of FujiMite[(R)] 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 generally 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 nonionic 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 pressure 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 days from one trial (CA95) to assess residue decline.  

For stone fruit harvested at a 6- to 8-day PHI following two foliar-directed applications of FujiMite[(R)] 5EC at 0.194-0.206 lb ai/A (with and without adjuvant), residues (and per-trial averages) of fenpyroximate, M-1, and combined residues, respectively, 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 residues of fenpyroximate 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 NIS adjuvant.  For the four side-by-side trial sites with both NIS and OSS plots, combined residues were slightly higher for the OSS plots than the NIS plots (1.2X to 1.4X), with the exception of one peach side-by-side trial (CA95) in which the combined residues were 1.2X higher for the NIS plot than the OSS plot.  For the one cherry trial with both NIS and COC plots, combined residues were higher for the COC plot by 2.7X.

The submitted peach residue decline data indicate that mean residues of fenpyroximate and combined residues decrease with increasing PHI.  Residues of M-1 were all <LOQ (0.05 ppm) at each sampling interval; therefore, residue decline could not be assessed.

TABLE 4.  Summary of Residue Data from Stone Fruit Trials with Fenpyroximate.
Commodity
                                   Plot 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
                                     0.249
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]  LAFT = 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 Growing 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 conducted 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 (NIS, OSS or COC) were entered into the spreadsheet, the plot with the highest residue was chosen.  The recommended tolerances for the combined residues of fenpyroximate 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 fenpyroximate and M-1 in/on fruit, stone, group 12 is thus 2.0 ppm. 

Potato

48903704.der1.docx

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[(R)] 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 NIS 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 days from two trials (09-NC18 and 09-MI11) to assess residue decline.  

Following two foliar broadcast or directed applications of the 0.4 lb ai/gal EC formulation of fenpyroximate at 0.198-0.215 lb ai/A, residues of fenpyroximate, M-1, and combined residues, respectively, 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 fenpyroximate 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]  LAFT = 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 vegetable, 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.  
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 analyzed using the OECD tolerance calculation procedures as all residues were <LOQ.  The recommended tolerance for the combined residues of fenpyroximate and M-1 is 0.10 ppm for the vegetable, 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 fenpyroximate and M-1 in/on grapes has been established at 1.0 ppm [40 CFR §180.566].  IR-4 has proposed to convert this tolerance to fruit, small, vine climbing, except fuzzy kiwifruit, subgroup 13-07F tolerance at the same level.  

As the proposed use on fruit, small, vine climbing, except fuzzy kiwifruit, subgroup 13-07F is identical to the existing use grapes on the product labels for FujiMite[(R)] 5EC, Portal[(R)], Akari[(R)] 5SC, the existing grape tolerance can be translated to fruit, small, vine climbing, except fuzzy kiwifruit, subgroup 13-07F.  


860.1520 Processed Food and Feed

Plum

48903703.der.docx

In one trial conducted in CA, plums received two foliar-directed applications of FujiMite[(R)] 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 commercial procedures.  Adequate descriptions were provided of the processing procedures; material balance summaries were not provided.

Following two foliar broadcast applications of FujiMite[(R)] 5EC at a total seasonal rate of 1.0 lb ai/A (~5X), average residues of fenpyroximate, M-1, and combined residues, respectively 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 fenpyroximate and M-1 may concentrate 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 Factor[2]

                                       
                                       
                                       
                                 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 factor = average residue in processed fraction / average residue in unprocessed RAC commodity.  
[3]  Mean of multiple analyses.
Conclusions:  Concentration following processing was observed in dried plums.  Multiplication of the plum HAFT residue (0.321 ppm) by the dried plum processing factor of 1.7X yields a value (0.55 ppm) which is less than the recommended RAC tolerance (2.0 ppm); therefore, a separate tolerance is not required for dried plums.

Potato

DER Reference List	48903704.der2.docx

In one trial conducted in ID, potatoes received two foliar broadcast applications of FujiMite[(R)] 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 days and processed into flakes, chips, and wet peel by the Food Technology Center (Caldwell, ID) using simulated commercial procedures.  Adequate descriptions were provided of the processing procedures, including material balance summaries.

Following two exaggerated-rate applications of fenpyroximate, average residues of fenpyroximate and M-1 were below the LOQ (<0.05 ppm) in/on potato tubers (RAC), flakes, chips, and wet peel; therefore, processing 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 fenpyroximate residues are unlikely to occur in the processed fractions of potato; therefore, separate tolerances are not required for potato processed fractions.


860.1650 Submittal of Analytical Reference Standards

Analytical standards for fenpyroximate (with expiration date of 11/20/2015) and its Z-isomer (with expiration date of 5/16/2014) are currently available in the EPA National Pesticide Standards Repository (personal communication with Theresa Cole, Analytical 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 fruits, cotton, and grapes (PP#s 0F06437 and 0E06519; DP#s 291925 and 291926, 8/20/03, G. Kramer; 45649913.der.wpd).  In the study, lettuce, radish, and wheat were planted 30, 120, and 365 days 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 fenpyroximate-related residues were <0.01 ppm in all samples of rotated lettuce, radish, and wheat planted at 30-, 120-, and 365-day PBIs except 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 fenpyroximate, 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 fenpyroximate, (E)-1,1-dimethylethyl4-[[[[(1,3-dimethyl-5-phenoxy-1H-pyrazol-4-yl) methylene] amino]oxy]methyl] benzoate and its Z­isomer, (Z)-1,1-dimethylethyl4-[[[[(1,3-dimethyl-5- phenoxy-lH-pyrazol-4-yl) methylene]amino]oxy] methyl]benzoate, calculated as the stoichiometric equivalent of fenpyroximate. 

Codex and Mexican MRLs are established for residues of fenpyroximate per se in/ grapes (fresh and dried).  Harmonization with the Codex and Mexican MRLs 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 MRLs.

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 data for potato were not entered into the tolerance spreadsheet because all treated samples bore combined residues below the LOQ of 0.10 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 Fenpyroximate. 
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

Remove from 40 CFR §180.566 (a)(1):
Grape
                                       
                                       




Attachments:
International Residue Limits sheet
Appendix I - Tolerance-Assessment Calculations



cc:  G. Kramer (RAB1)
RDI:  RAB1 Chemists (12/12/12)
G.F. Kramer:S10957:PY-S:(703)305-5079:7509P:RAB1

Template Version September 2005
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-1H-pyrazol-4-yl) methylene] amino]oxy]methyl]benzoate and its Z-isomer, (Z)-1,1-dimethylethyl 4-[[[[(1,3-dimethyl-5-phenoxy-1H-pyrazol-4-yl)methylene] amino]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.




                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
                                     0.348
- 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

