Page 1 of 22 UNITED STA

TES ENVIRONMENTA L PROTECTION AGENCY WASHINGTON, D.C. 20460OFFICE OF CHEMICAL SAFETY AND POLLLUTION PREVENTION MEMORANDUM Date : 11 / 17 / 10 SUBJECT: Fluoxastrobin . Petition for the Establishment of Permanent To lerances fo r Use s

on Squash/Cucumber Subgroup 9B . Summary of Analy tical Chemistry

and Residue Data . PC Code: 028869 DP Barcode: 380846 Decision No.: 433137 Registration No. : 66330 - 64 Petition No.: NA Regulatory Action: Section 3 R egistration Risk Assessment Type: NA Case No.: NA T XR No.: NA CAS No.: 361377 - 29 - 9 MRID No.: 48088301 40 CFR: 180 . 609 FROM: Meheret Negussie , Chemist

Risk Assessment Branch III Health Effects Division (HED 7509P) THROUGH: Leung Cheng , Senior Chemist

Risk Assessment Branch III Health Effects Division (HED 7509P) TO: Nancy

Tsaur, Risk Assessor RAB III/HED (HED 7509P) and Tony Kish, RM# 22 Fungicide Branch R egistration Division ( RD 7505P)Fluoxastrobin Summary of Analytical Chemistry and Residue Data DP#: 380846

Page 2 of 22 Executive Summary Fluoxastrobin is a fungicide used for the control of fungal diseases in tuberous and corm vegetables, fruiting vegetables, the lea f petiole vegetables, peanuts, low growing berries, field corn, wheat, soy

beans, peanuts, and as a seed treatment for potato and peanut, and as a soilborne/seedling disease control. It works by interfering with respiration in plant - pathogenic fungi and is a potent inhibitor of spore germination and mycelial growth. It belongs to the strobilurin class of fungicides (Group 11), also termed methoxyacrylates. Fluoxastrobin is the accepted common name for the pesticidally active E isomer of [2 - [[6 - (2 - chloroph enoxy ) - 5 - fluoro - 4 - py

rimidinyl]oxy]phenyl](5,6 - dihydro - 1,4,2 - dioxazin - 3 - yl )methanone O - methyloxime . The Z - isomer of fluoxastrobin is ty pically present at much lower levels ( E : Z ratio of approximately

90:10). The petitioner has requested that fluoxastrobin ( E- isomer only

) be designated as the active ingredient. Arysta Li feScience North America (Arysta) is proposing the establishment of tolerances for combined residues of the fungicide fluoxastrobin ( 1 E) - [2 - [[6 - (2 - chlorophenoxy ) - 5 - fluoro - 4 - py rimidinyl]oxy] phenyl](5,6 - dihydro - 1,4,2 - dioxazin - 3 - yl )methanone O - methyloxime and its Zisomer (1 Z

) - [2 - [[6 - (2 - chlorophenoxy ) - 5 - fluoro - 4 - py

rimidinyl]oxy]phenyl](5,6 - dihydro - 1,4,2 - dioxazin - 3 - yl )methanone O - methyloxime in/on the following raw agricultural c ommodities:

Cro p subgroup 9B Squash/Cucumbers ....................... 0. 50 ppm Inconjunction with this petition, Arysta is requesting amended registration of the 4 lb ai/gal suspension concentrate (SC) formulation of fluoxastrobin, Fluoxastrobin 480 SC Fungicide (EPA Reg. No. 66330 - 64) , to ad d uses on squash/cucumber subgroup 9B . The product is proposed for up to four foliar applications to squash/cucumber subgroup 9B at up to 0.16 lb ai/A/application for a total application rate of 0.68 lb ai/A; a 1 - day preharvest interval (PHI) is proposed. For soilborne disease control , a rate of 0.16 - 0.24 fl. oz./ 1 000 row feet ( 0.005 - 0.075 lb ai/A) is proposed . Tolerances for combined residues of fluoxastrobin and its Z - isomer in/on primary

crop commodities are established under 40 CFR §180.609(a)(1) at levels ranging from 0.010 ppm (peanut and the tuberous and corm vegetable subgroup 1C) to 20.0 ppm (peanut hay ). Tolerances are established under 40 CFR §180.609(a)(2) for the combined residues of fluoxastrobin, its Z

- isomer, and i ts phenoxy- hydroxy py rimidine metabolite, 6 - (2 - chlorophenoxy

) - 5 - fluoro - 4 - py

rimidinol, in cattle, goat, horse, and sheep commodities at levels ranging from 0.02 ppm (milk) to 0.50 ppm (milk fat); no tolerances are currently established for poultry commoditie s. Tolerances for indirect or inadvertent combined residues of fluoxastrobin and its Z - isomer are established under 40 CFR §180.609(d) for rotated crop commodities [alfalfa forage and hay ; cotton gin by products; forage, fodder, and s traw of cereal grains except corn (crop group 16); grass forage and hay ; and foliage of legume vegetables (crop group 7) ] at 0.020 - 0.50 ppm. The nature of the residue in plants and livestock is adequately understood. In plants, the results of metabolism studies conducted on wheat, peanut, and tomato indicate that metabolism of fluoxastrobin is similar in dissimilar crops. HED has concluded that the residues of concern for risk assessment and tolerance setting purposes are fluoxastrobin and it s Z - isomer. AcceptableFluoxastrobin Summary of Analytical Chemistry and Residue Data DP#: 380846

Page 3 of 22 metabolism studies on goats and laying hens are also available. The available data indicate that the metabolism in goats and hens is similar. Metabolism of fluoxastrobin was found to be more extensive in livestock than in plants , and metaboli tes consisting of single rings (e.g., 2 - chlorophenol and 2 - cyanophenol) were observed in each of the livestock metabolism studies. HED has concluded that in livestock commodities, the residues of concern are fluoxastrobin, its Z - isomer, and the phenoxy- hydroxy py rimidine metabolite (HEC 7154) for risk assessment and tolerance setting purposes . Acceptable high performance liquid chromatography methods with tandem mass spectroscopic detection (L C/MS/MS) are available for tolerance enforcement for plant and livestock commodities. Bayer AG m ethod 00604 and confirmatory method 00946 have been adequately validated for the determination of residues of fluoxastrobin and its Z - isomer in plant commodities , and Bayer AG method 00691 and confirmatory method 00945 have been adequately

validated for determination of fluoxastrobin, its Z - isomer, and HEC 7154 in ruminant commodities . Samples from the submitted crop field trials were analy zed for residues of fluoxastrobin and its Z - isomer using an acceptable LC/MS/MS method. Samples of cucumber and squash were analy zed using Bayer AG Method 00668 . The method was adequately validated prior to and

/or in conjunction with the analysis of the field trial . The validated limit of quantitation ( LOQ ) was 0.01 ppm for combined residues of fluoxastrobin and its Z - isomer in/on all crop commodities. Adequate multiresidue methods testing data have been submitted. The data indicate that t he multiresidue methods are not adequate for enforcement of tolerances for fluoxastrobin . Ade quate storage stability data are available to support storage conditions and intervals of samples from the cucumber and squash field trials . There are no livestock feedstuffs associated with the proposed use s on squash/cucumber subgroup 9B . T he submitted crop field trial data for cucumbers and summer squash reflect the proposed use pattern s and are acceptable p ending submission of a revised label and an additional field trial data for cucumber in region 2 . T he submitted data will support the proposed tolerances for Squash/cucumber subgroup 9B at 0.5 ppm . The nature of the residue in rotational crops is understood b ased on an adequate confined rotational crop study . HED has concluded that the residues of concern for rotational crops for risk assessme nt and tolerance setting purposes are fluoxastrobin and its Z - isomer. Adequate field rotational crop data are available which indicate that residues of fluoxastrobin and its Z - isomer may accumulate in rotated crops. The available data support the establi shed tolerances for indirect or inadvertent residues established under 40 CFR 180.609(d), and indicate that the following rotational crop restrictions are appropriate for fluoxastrobin: a 0 - day plantback interval (PBI) for any

crop listed on the label; a 30 - day PBIfor the root vegetables subgroup (e.g., carrot, radish, sugar beet, and turnip) , bulb vegetables (e.g., onion and garlic) , leafy greens subgroup (e.g., lettuce and spinach) , B rassica vegetables (e.g., broccoli, cauliflower, cabbage,Fluoxastrobin Summary of Analytical Chemistry and Residue Data DP#: 380846

Page 4 of 22 and mustard greens) , alfalfa, cotton, legume vegetables (dry and succulent peas and beans) , cereal grains, and forage grasses; and a 12 - month PBIfor all other crops. There are no Codex, Canadian, or Mexican maximum residue limits ( MRL s ) established for fluoxastrobin . Regulatory Recommendations and Residue Chemistry Deficiencies HED has examined the residue chemistry database for fluoxastrobin. Pending submission of revised Section s B , F, and resolution of the deficiencies identified below, there are no residue ch emistry issues that would preclude granting conditional registration for the requested uses of fluoxastrobin on squash/cucumber subgroup 9B or establishment of the following tolerances for combined residues of fluoxastrobin and its Z - isomer : Squash/ c ucumb er subgroup 9B ................................ ... 0.50 ppm A human health risk assessment is forthcoming. Note to PM: According to HED’s Interim Guidance on Tolerance Expressions (5/27/09, S. Knizner), the tolerance expressions for fluoxastrobin should be revised as follow: Under 40 CFR §180.609(a)(1) and §180.609(d): “Tolerances are established for residues of fluoxastrobin, including is 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 (1 E) - [2 - [[6 - (2 - chlorophenoxy) - 5 - fluoro 4 - pyrimidinyl]oxy]phenyl](5,6 - dihydro - 1,4,2 - dioxazin - 3 -yl)methanone O - methyloxime and its Z - isomer , (1 Z

) - [2 - [[6 - (2 - chlorophenoxy) - 5 - fluoro - 4 - pyrimidinyl]oxy]phenyl](5,6 - dihydro - 1,4,2 - dioxazin - 3 -yl)methanone O - methyloxime. Under 40 CFR §180.609(a)(2): “Tolerances are established for residues of fluoxastrobin, including is metabolites and degradates, in or on the commodities in the table below. Compliance with the tolerance levels specified be low is to be determined by measuring only the sum of (1 E) - [2 - [[6 - (2 - chlorophenoxy) - 5 - fluoro - 4 - pyrimidinyl]oxy]phenyl](5,6 - dihydro - 1,4,2 - dioxazin - 3 -yl)methanone O- methyloxime, its Z - isomer , (1 Z

) - [2 - [[6 - (2 - chlorophenoxy) - 5 - fluoro - 4 - pyrimidinyl]oxy]phenyl](5,6 - dihydro - 1,4,2 - dioxazin - 3 -yl)methanone O - methyloxime, and the phenoxy hydroxypyrimidine metabolite, 6 - (2 - chlorophenoxy) - 5 - fluoro - 4 - pyrimidinol, calculated as the stoichiometric equivalent of fluoxastrobin. 860.1200 Directions for Use

 The proposed use di rections for squash/cucumber subgroup 9B should be revised to correct the application rate from a range of 0.09 to 0.16 lbs ai/A to a range of 0.09 to 0.18 lb ai/A.

 The statement “Do not apply more than 21.8 fl oz (0.68 lbs ai) of EVITO 480 SC per acre pe r year” should be revised to “Do not apply more than 22.8 fl oz (0.72 lbs ai/A ) of EVI TO 480 SC per acre per year”.Fluoxastrobin Summary of Analytical Chemistry and Residue Data DP#: 380846

Page 5 of 22  The proposed use directions for squash/cucumber subgroup 9B should be revised to include use of a non - ionic surfactant (NI S). 860.1500 Cro p Field Trials

 To fulfill geographic distribution requirements, an additional cucumber field trial must be conducted in region 2 . 860.1550 Proposed Tolerances

 A revised Section F is needed that reflect correct commodity definition (Table 10). 860.165 0 Submittal of Analy tical Reference Standards

 Arysta must provide an analy tical reference standard of the metabolite HEC 7154 to the EPA National Pesticide Standards Repository . Background T he chemical structure and nomenclature of fluoxastrobin , its Z - isomer, and the phenoxyhydroxy py rimidine metabolite are presented in Table 1. The physicochemical properties of the technical grade of fluoxastrobin are presented in Table 2 . Table 1. Test Compound Nom enclature. Compound Cl O N N F O O O N

N O C H3 Common name Fluoxastrobin Company experimental name HEC 5725 IUPAC name (E) - {2 - [6 - (2 - chlorophenoxy) - 5 - fluoropyrimidin - 4 - yloxy]phenyl}(5,6 - dihydro 1,4,2 - dioxazin - 3 - yl)methanone O - methyloxime CAS name (1 E) - [2 - [[6 - (2 - chlorophenoxy) - 5 - fluoro - 4 - pyrimidinyl]oxy]phenyl](5,6 - dihydro 1 ,4,2 - dioxazin - 3 - yl)methanone O - methyloxime CAS registry number 361377 - 29 - 9 Formula C 21 H 16 ClFN 4 O 5 End - use product (EP) 4 lb ai/gal SC formulation ( Fluoxastrobin 480 SC/EvitoTM 480 SC Fungicide 1 ; EPA Reg. No. 66330 - 64)Fluoxastrobin Summary of Analytical Chemistry and Residue Data DP#: 380846

Page 6 of 22 Table 1. Test Compound Nom enclature. Compound Cl O N N F O O O N

N O C H3 Common name Fluoxastro bin Z - isomer Chemical name (1 Z ) - [2 - [[6 - (2 - chlorophenoxy) - 5 - fluoro - 4 - pyrimidinyl]oxy]phenyl](5,6 - dihydro 1,4,2 - dioxazin - 3 - yl)methanone O - methyloxime Compound Cl O N N F O H

Common name HEC 7154 Chemical name 6 - (2 - chlorophenoxy) - 5 - fluoro - pyrimidinol 1 The current labe l for Fluoxastrobin 480 SC Fungicide (EPA Reg . No. 66330 - 64) indicates that the master label is the basis for three different labels, including EvitoTM 480 SC Fungicide. Table 2. Physicochemical Properties of Technical Grade Fluoxastrobin. Parameter Value Reference (MRID) Melting range 103 - 105 oC 45865525 pH 6.3 (1% in CIPAC - D water) 45865520 Density 1.4216 ± 0.0025 g/mL 45865303 Water solubility at 20 oC : 0.0019 g/L; 0.0024 g/L at pH 4 0.0023 g/L at pH 7 0.00227 g/L at pH 9 45865520, 45865525 Solvent solubility at 20 oC : n - heptane 0.05 g/L xylene 38 g/L dichloromethane >250 g/L 2 - propanol 6.7 g/L 1 - octanol 1.1 g/L p olyethylen e glycol 400 100 - 250 g/L acetone >250 g/L ethyl acetate >250 g/L acetonitrile >250 g/L dimethylsulfoxide >250 g/L 45865520, 45865525

Vapor pressure <1x10 - 5 hPa (20 oC) 45865525 Dissociation constant, pKa No acidic or basic properties in the pH range between 4 and 9; estimated to be - 2.1 ± 0.3 45865303 Octanol/water partition coefficient, Log(P OW) 2.85 (20 oC); P OW = 708 45865525 UV/visible absorption spec trum Peak maxima (nm) 250; molar absorptivity (1000 cm2/mol) 19358; sample melting point 103.1 - 107.7 oC 45865303Fluoxastrobin Summary of Analytical Chemistry and Residue Data DP#: 380846

Page 7 of 22 860.1200 Directions for Use Arysta has submitted proposed use directions (Section B) for the 4 lb ai/gal SC formulation of fluoxastrobin (Fluoxastrobin 480 SC Fungicide; EPA Reg. No. 66330 - 64) in/ on squash/ cucumber subgroup 9B. The proposed use directions for squash/ cucumber subgroup 9B are presented in Table 3. Table 3 . Summary of Directions for Use of Fluoxastrobin . Applic. Timing, Type , and Equip. Formulation

[EPA Reg. No.] Applic.

Rate lb ai/A Max.

No. Applic. per Season Max.

Seasonal Applic. Rate (lb ai/A) PHI

(days) Use Directions and Limitations Squash/Cucumber subgroup 9B : Chayote (fruit); Chinese waxgourd (Chinese preserving me lon); cucumber; gherkin; gourd, edible (includes hyotan, cucuzza, hechima, Chinese okra); Momordica spp (includes balsam apple, balsam pear, bitter melon , Chinese cucumber); pumpkin; squash, summer (includes crookneck squash, scallop squash, straightneck squash, vegetable marrow, and zucchini) ; and squash, winter (includes butternut squash, calabaza,

hubbard squash, acorn squash, and spaghetti squa sh) Broadcast, Foliar, Ground , Chemigation 4 lb ai/gal SC

[66330 - 64] 0. 09 - 0. 16

(3 - 5.7 fl. oz/A) 4 0. 68

( 21. 8 fl. oz/A) 1 Applications are to begin

preventatively and continue as needed on a minimum 7 - 14 day interval . Use higher rates when disease is severe. For belly- rot control, the first application should me made at the 1 - 3 leaf crop stage, and the second application 10 - 14 days later, or at vine tip - over, whichever occurs first. Soilborne Disease Control (Root rot) 0.005 - 0.0075 lb/1000 row feet ( 0.16 - 0.24 fl. oz/1000 row feet) Do not use the 0.24 fl oz/1000 row feet rate on row s spaced narrower than 22 inches. Do not use the 0.16 fl oz/1000 row feet rate on row s spaced less than 15 inches. For twin row s spaced 7.5 - 8” apart on 30 inch centers, use the 0.16 fl oz/1000 row

feet rate for 15” row s only. The proposed use directions for squash/ cucumbers include the following resistance management restriction: Alternate every application of the product with at least one application of another registered, non - Group 11 fungicide. Do not make more than 4 applications of EVITO 480 SC fungicide and or a Group 11 fungicide per season. Do not use EVI TO 480 SC for control of gummy stem blight where resistance to Group 11 (Qol) fungicides exists.Fluoxastrobin Summary of Analytical Chemistry and Residue Data DP#: 380846

Page 8 of 22 The use directions submitted in Section B do not include application spray volumes , specifications for applicati on via chemigation and adjuvant use . The registered label recommends a minimum spray volume of 10 gal/A for ground equipment. The registered label states that chemigation applications are to be made through sprinkler- ty pe irrigation systems only . The re gistered label does not specify adjuvant use in any

tank - mix partner. The use directions submitted in Section B prohibits use of EVITO 480 SC to squash/cucumber subgroup 9B crops grown in a greenhouse. In addition, it prohibits tank mix with emulsifiable concentrate ( EC ) - based insecticides, or the following products : malathion, Kelthane ® , Thiodan ®, Phaser®, Lannate ® , L orsban ® , M - Pede ®, or Botran ® . The use directions submitted in Section B do not include rotational crop restrictions. The following crop restrictions appear on the registered label: 0 - day PBIfor any

crop listed on the label; 30 - day

PBIfor root vegetables (e.g., carrot, radish, sugar beet, and turnips), bulb vegetables (e.g., onion and garlic), leafy greens subgroup (e.g., lettuce and spi nach), Brassica vegetables (e.g., broccoli, cauliflower, cabbage, and mustard greens), alfalfa, cotton, legume vegetables (dry

and succulent peas and beans), cereal grains, and forage grasses; and a 12 - month PBIfor all other crops. Conclusions . The subm itted use directions are adequate to allow evaluation of the residue data relative to the proposed use. With the change s to the proposed use noted below, the submitted field trial data for cucumbers and squash reflect the maximum proposed use rates , the m inimum retreatment intervals ( RTI s ) , and the proposed PHI s :  The proposed use directions for squash/cucumber subgroup 9B should be revised to correct the application rate from 0.09 to 0.16 lbs ai/A to 0.09 to 0.18 lbs ai/A.

 The statement “Do not apply more than 21.8 fl oz (0.68 lbs ai) of EVITO 480 SC per acre per year” should be revised to “Do not apply more than 22.8 fl oz (0.72 lbs ai/A ) of EVI TO 480 SC per acre per year”.

 The proposed use directions for squash/cucumber subgroup 9B should be revised t o include use of a NI S . 860.1300 Nature of the Residue - Plants Residue Chemistry Memo DP# 289106 , 1/25/05, W. Wassell (PP# 3F6556 ) The nature of the residue in plants is adequately understood based on acceptable metabolism studies in wheat, peanuts , an d tomatoes. The data indicate that metabolism is similar in three dissimilar crops. HED previously conclude d that the residues of concern in primary crops for risk assessment and tolerance setting purposes are fluoxastrobin and its Z - isomer.Fluoxastrobin Summary of Analytical Chemistry and Residue Data DP#: 380846

Page 9 of 22 860.130 0 Nature of the Residue - Livestock Residue Chemistry Memo DP# 334234, 10/30/ 0 8 , A . Acierto (PP#3F6556) Residue Chemistry Memo DP# 289106 , 1/25/05, W. Wassell (PP# 3F6556 ) The nature of the residue in ruminants and poultry is adequately understood based o n acceptable metabolism studies with goats and hens. The data indicate that metabolism is similar in ruminants and poultry . Metab olism of fluoxastrobin was found to be more extensive in livestock than in plants ; metabolites consisting of single rings (e. g., 2 - chlorophenol and 2 - cyanophenol) were observed in each of the livestock metabolism studies. HED previously conclude d that the residues of concern for livestock commodities for risk assessment and tolerance setting purposes are fluoxastrobin, its Z

- is omer, and HEC 7154 . 860.1340 Residue Analytical Methods Residue Chemistry Memo DP# 334234, 10/30/ 0 8 , A . Acierto (PP#3F6556) Residue Chemistry Memo DP# 289106 , 1/25/05, W. Wassell (PP# 3F6556 ) Plant commodity

methods Enforcement m ethod: Acceptable LC/M S/MS methods are available for tolerance enforcement for plant commodities. Bayer AG Method 00604 and the confirmatory Method 00946 have been adequately

validated for the determination of residues of fluoxastrobin and its Z - isomer in/on plant commodities. Data collection methods: Samples of cucumber, cantaloupe, and squash from the submitted crop field trials were analy

zed for residues of fluoxastrobin and its Z - isomer using an acceptable LC /MS/MS method . All s amples from the cucurbit vegetable crop fie ld trials were analy zed using Bayer AG Method 00668 . T he methods were adequately validated prior to and

/or in conjunction with the analysis of the field trial. The validated L OQs were 0.01 ppm for combined residues of fluoxastrobin and its Z - isomer in/on cucumber, cantaloupe, and squash samples . For Method 00668, samples (~ 1g) were soak ed in acetone:water (75:25 , v : v) for 30 minutes , then subjected to microwave extraction for 1.5 minutes at 40 °C and centrifuged. The residues were extracted twice more, once with microwave extraction and once at ambient temperature, and the resulting supernatants were combined. The combined extracts were evaporated under nitrogen to aqueous remainder, then subjected to cleanup via solid phase extraction on a Bond Elut ENV cartridge . Residues were eluted with ethyl acetate, evaporated to dry ness, then redissolved in acetonitrile:water (60:40, v:v) for analysis by HPL C /MS/MS. Li vestock commodity

methods Acceptable LC/MS/MS methods are available for tolerance enforcement for livestock commodities. Bayer AG Method 00691 and the confirmatory Method 00945 have been adequately

validated for determination of fluoxastrobin, its Z - isomer, and HEC 7154 in ruminant commodities. The method L OQs for fluoxastrobin ( E +Z isomers) and HEC 7154 are 0.01 ppm for each analy

te in milk, muscle, and fat, and 0.02 ppm for each analy te in liver and kidney .Fluoxastrobin Summary of Analytical Chemistry and Residue Data DP#: 380846

Page 10 of 22 Conclusions. The residue analy tical methods data are adequate. Acceptable methods are available for tolerance enforcement purposes for the residues of concern in/on plant and livestock commodities, and samples of cucumber, cantaloupe, and squash from the submitted crop field trials were analy

zed for residues of fluoxastrobin and its Z - isomer using acceptable data collection methods. 860 .1360 Multiresidue Methods Residue Chemistry Memo DP# 289106 , 1/25/05, W. Wassell (PP# 3F6556 ) Acceptable multiresidue methods test data were previously submitted for f

luoxastrobin, its Z

isomer, and HEC 7154. The data indicate that the multiresidue meth ods are not adequate for tolerance enforcement o f fluoxastrobin residues in/on plant or livestock commodities. The results were forwarded to FDA. 860.1380 Storage Stability Residue Chemistry Memo DP# 334234, 10/30/ 0 8 , A . Acierto (PP#3F6556) Residue Che mistry Memo DP# 289106 , 1/25/05, W. Wassell (PP# 3F6556 ) Sufficient storage stability data are available to demonstrate that combined residues of fluoxastrobin and its Z

- isomer are stable during frozen storage (≤ - 15 °C ) in/on raw agricultural crop commodities for up to ~20 - 23 months. The data reflect five representative crops: an oilseed (soy

bean), a non - oily

grain (wheat), a leafy

vegetable (mustard greens), a tuber crop (potato), and an acidic fruiting vegetable (tomato) , and demonstrate that residues o f fluoxastrobin and its Z - isomer are stable during frozen storage in/on soy bean seed for ~21 months, mustard greens, tomato, wheat grain, hay, and straw for ~22 months, peanut and potato for ~23 months, and wheat forage for ~20 months. The storage duration s and conditions of samples from the submitted crop field trials and processing studies are presented in Table 4 . TABLE 4 . Summary of Storage Conditions and Durations of Samples fromCrop Field Trials . Matrix Storage Temperature (°C) Actual Storage D uration 1 Interval of Demonstrated Storage Stability Cucumber

~ - 20 196 - 227 days (6.5 - 7.5 months) Residues of fluoxastrobin and its Zisomer are stable during frozen storage in/on five diverse crops for up to 20 - 23 months. 2 Cantaloupe 11 7 - 21 8 days (3.9 - 7 .2 months) Summer Squash 12 3 - 22 5 days (4 - 7.5 months) 1 I nterval from harvest to completion of analysis. Method extraction and analysis procedures were conducted over several days; the durations from initial to final extraction were 2 - 7 days, and analyses were conducted over 0 - 2 days; analysis of final extracts was completed within 0 - 1 day of extraction. 2 Refer to DP# 289106, 01/25/05, W. Wassell. Conclusions . The available storage stability data for fluoxastrobin on representative crops are adequ ate to support the storage durations and conditions of samples of cucumber, cantaloupe, and summer squash from the submitted crop field trials.Fluoxastrobin Summary of Analytical Chemistry and Residue Data DP#: 380846

Page 11 of 22 860.1400 Water, Fish, and Irrigated Crops This guideline requirement is not relevant to the current petition as there are no aquatic uses currently proposed for fluoxastrobin. 860.1460 Food Handling This guideline requirement is not relevant to the current petition as there are no food handling uses being proposed for fluoxastrobin. 860.1480 Meat, Milk, Poult ry, and Eggs There are no livestock feedstuffs associated with the proposed use s on squash/cucumber subgroup 9B . The dietary burdens for fluoxastrobin residues in livestock diets will not be affected by

the subject action; therefore, data requirements pertaining to meat, milk, poultry, and eggs are not relevant to the proposed uses. 860.1500 Crop Field Trials DER Reference: 48088301 .der .doc ( Squash/cucumber subgroup 9B ) Arysta has submitted field trial data for fluoxastrobin on cucumber, cantaloupe, and summer squash as the representative crops of the cucurbit vegetable, crop group 9. Seventeen field trials were conducted in the U.S. during the 2008 growing season. Six cucumber trials were conducted in region 2 (GA; 2 trials), 3 (FL; 1 trial), 5 (MI ; 2 trials), and 6 (OK; 1 trial). Six cantaloupe trials were conducted in region 10 (CA; 3 trials) and region 2 (GA; 1 trial), 5 (MI ; 1 trial), 6 (TX; 1 trial). Five summer squash trials were conducted in region 1 (PA; 1 trial), 2 (GA; 1 trial), 3 (FL; 1 trial), 5 (MI ; 1 trial) and 10 (CA; 1 trial). At each test location, four foliar broadcast applications of a 4 lb ai/gal SC formulation of fluoxastrobin were made at 0.17 - 0.1 9 lb ai/A/application, with a 6 - to 8 - day RTI , for a total rate of 0.68 - 0. 73 lb ai/A. Applications were made at BBCH 19 - BBCH 90 growth stages using ground equipment in spray volumes of 14 - 29 gal/A . For some trials, growth stages were not specified as BBCH growth stages. A NI S was added to the spray mixtures in some trials . In the cantaloupe trials, adjuvant was used at one location only . In the squash trials, adjuvant was used at all locations except one. In the cucumber trials, adjuvant was used at 2 of the 5 trial locations. Samples of mature cucumber, cantaloupe, and summer s quash fruits were collected 1 day after the last application . Samples of cucumber , cantaloupe, and summer squash were harvested at 0 - , 1 - , 3 - , 7 - , and 10 - day

PHI s to evaluate residue decline. Samples of cucumber, cantaloupe, and summer squash were analy z ed for residues of fluoxastrobin (

E- isomer) and its Z

- isomer using an LC /MS/MS method , Bayer AG Method 00668. The method L OQ was 0.01 ppm for combined residues of fluoxastrobin and its Z - isomer in cucurbit vegetables. Quantifiable residues (0.01 - 0.88) were observed in treated cucumber, cantaloupe, and squash samples. The method is adequate based on acceptable method validation and concurrent recovery

data. The fortification levels used in concurrent method validation were adequate to bracket field trial residue results.Fluoxastrobin Summary of Analytical Chemistry and Residue Data DP#: 380846

Page 12 of 22 Samples of cucurbit vegetables were stored frozen for up to 7.5 months prior to analysis. Acceptable storage stability data were previously

submitted which indicate that residues of fluoxastrobin and its Z

- isomer are stable during fro zen storage in/on various representative crops for up to 23 months. These data are adequate to support the storage conditions and durations of samples from the cucurbit vegetables crop field trial study . Combined residues of fluoxastrobin and its Z - isomer were 0.04 - 0.18 ppm in/on cucumber, 0.08 - 0.88 ppm, in/on cantaloupe, and 0.01 - 0.18 ppm in/on summer squash samples. In the cantaloupe trials, adjuvant was used at one location only . The residue for the trial with adjuvant was 0.09 ppm; the range for tri als without adjuvant was 0.14

– 0.83 ppm. In the squash trials, adjuvant was used at all locations except one. The residue was 0.04 ppm where adjuvant was not used, and ranged from 0.06 to 0.15 ppm where adjuvant was used. In the cucumber trials, adjuvant was used at 2 of the 5 trial locations. Residues ranged from 0.04 to 0.09 ppm where adjuvant was used and from 0.07 to 0.17 ppm where adjuvant was not used. For all crops, no side - by- side trials were conducted with and without adjuvant, and therefore it is impossible to separate the effect of adjuvant use from the effects of trial location . Inthe residue decline studies, combined residues of fluoxastrobin and its Z - isomer generally declined with increasing sampling interval. Table C.5 . Summary of Residue Data fromC ucurbit Field Trials with Fluoxastrobin . Crop matrix Total Applic.

Rate (lb ai/A) PHI

(days) Residue Levels (ppm) 1

N 2 Min. Max. HAFT 3 Median Mean Std. Dev. C ucurbit Vegetables (proposed use = 0.017 lb ai/A total appli cation rate, 1 - day PHI) Cucumber 0.68 - 0.71 1 12 0.04 0.18 0.17 0.08 0.09 0.04 Cantaloupe 0.68 - 0.73 1 12 0.08 0.88 0.83 0.34 0.35 0.25 Summer squash 0.68 - 0.71 1 10 0.01 0.18 0.16 0.08 0.08 0.05 1 Combined residues of fluoxastrobin and its Z - isomer. 2 N = number of samples (includes only target PHI samples from decline trials) 3 HAFT = H ighest average field trial Conclusions . The submitted cucumber and summer squash field trial studies are a cceptable and reflect the proposed use patterns . Samples w ere analy zed for residues of fluoxastrobin and its Zisomer using acceptable methods, and the studies are supported by adequate storage stability data . For cucumbers, the number of field trials is not in accordance with OPPTS 860.1500 . S ix trials were conducted ; however , the two field trial s conducted in region 2 could not be counted as independent trials since both trials have the same address. One additional cucumber trial must be conducted in region 2. Pending revision of the proposed use patterns and submission of the outstanding field trial data , the submitted field trial data will support the proposed tolerance of 0.5 ppm for squash/cucumber subgroup 9B. The field trial data for cucumber and summer squash were separately entered into the Agency ’s tolerance spreadsheet as specified by the Guidance for Setting Pesticide Tolerances Based onFluoxastrobin Summary of Analytical Chemistry and Residue Data DP#: 380846

Page 13 of 22 Field Trial Data SOP to determine an appropriate tolerance level; see Appendix II. The tolerance spreadsheet recommends individual tolerances of 0. 25 ppm fo r cucumber and 0. 5 ppm for summer squash. Because the minimum and maximum recommended tolerances differ by less than 5x, a crop group tolerance is appropriate for squash/cucumber subgroup 9B . The recommended value is 0. 5 ppm, the maximum of the recommend ed individual tolerances. The recommended tolerance level is the same as the level proposed by the petitioner (0.5 ppm) . 860.1520 Processed Food and Feed HED does not require residue data for any processed commodities associated with squash/cucumber s ubgroup 9B . Therefore, data requirements for processed food and feed are not relevant to this tolerance petition. 860.1650 Submittal of Analytical Reference Standards Analy tical standards for f

luoxastrobin and Z - fluoxastrobin are currently available in the EPA National Pesticide Standards Repository (Repository ) ( email communication with Charles Stafford , ACB, 9/23 / 10 ), with expiration dates of 2011 - 2018 ; the reference standard for the metabolite HEC 7154 [6 - (2 - chlorophenoxy ) - 5 - fluo ro - 4 - py

rimidinol] has expired and must be submitted to the Repository . Standards were supplied by the previous registrant, Bayer CropScience. ACB requests that the new registrant, Arysta, provide analy tical reference standard of the metabolite HEC 7154 t o the Repository Conclusion s . The new registrant, Arysta, must provide an analy tical reference standard of the metabolite HEC 7154 to the Repository . 860.1850 Confined Accumulation in Rotational Crops Residue Chemistry Memo DP# 334234, 10/30/ 0 8 , A . Acierto (PP#3F6556) Residue Chemistry Memo DP# 289106 , 1/25/05, W. Wassell (PP# 3F6556 ) Residue Chemistry Memo D P# 292422, 1/24/05, S. Winfield Available confined rotational crop data are adequate to satisfy data requirements and to delineate the nature of the residue in rotated crop commodities. The confined rotational crop studies indicate the potential for quantifiable residues of fluoxastrobin in rotated crop commodities. HED previously conclude d that the residues of concern for rotational crops for risk assessment and tolerance setting purposes are fluoxastrobin and its Z - isomer.Fluoxastrobin Summary of Analytical Chemistry and Residue Data DP#: 380846

Page 14 of 22 860.1900 Field Accumulation in Rotational Crops Residue Chemistry Memo DP# 334234, 10/30/ 0 8 , A . Acierto (PP#3F6556) Residue Chemistry Memo DP# 289106 , 1/25/05, W. Wassell (PP# 3F6556 ) A cceptable limited field rotational crop and extensive field rotational crop studies w ere previously reviewed under PP#3F655 6 . Adequate field rotational crop data are available on the representative crops of mustard greens (leafy vegetable), turnips (root vegetable), and wheat (cereal grain). The primary crops each received four spray applications of fluoxastrobin at ~0.18 lb ai/A, for total application rates of ~0.72 lb ai/A. The limited field rotational crop data, which indicated no quantifiable residues of fluoxastrobin and its Z - isomer in mustard greens and turnip roots and tops at a 30 - day PBI , are adequate to support the proposed 30 - day PBIfor root and tuber vegetables, bulb vegetables, leafy vegetables, and Brassica vegetables . Extensive field rotational crop studies reflecting a 1 - month PBIsupport the established indirect or inadvertent tolerances on alfalfa forage and hay ; cotton gin by products; forage, fodder, and straw of cereal grains; grass forage and hay ; and foliage of legum e vegetables. The se data support the established rotational crop restrictions on the master label (EPA Registration No. 66330 - 64). 860.1550 Proposed Tolerances Residue Chemistry Memo D P#s 356953 and 357691, 7/8/09, M. Negussie (PP#8F7406 and PP#8F7437 ) Tolerances for plant commodities are established under 40 CFR §180.609(a)(1) for the combined residues of fluoxastrobin and its Z - isomer ; tolerances for livestock commodities are established under 40 CFR §180.609(a)(2) for combined residues of fluoxastrobin, its Z - isomer, and the phenoxy- hydroxy

py rimidine metabolite. The tolerance expression proposed by the petitioner is appropriate for Squash/cucumber subgroup 9B . The tolerance proposed by Arysta is the same as the recommended tolerance by RAB3 and i s listed in Table 10 , along with the revised commodity definition. Pending submission of an additional field trial for cucumber, adequate field trial data reflecting the proposed use patterns are available for purposes of establishing tolerances in Squa sh/cucumber subgroup 9B . The field trial data for cucumber and squash were separately entered into the Agency ’s tolerance spreadsheet as specified by the Guidance for Setting Pesticide Tolerances Based on Field Trial Data SOP (rev. August 2009) to determi ne an appropriate tolerance level; see Appendix II. The tolerance spreadsheet recommends individual tolerances of 0. 25 ppm for cucumber and 0.5 ppm for summer squash. Because the minimum and maximum recommended tolerances differ by less than 5x, a crop group tolerance is appropriate for squash/cucumber subgroup 9B . The recommended value is 0.5 ppm, the maximum of the recommended individual tolerances. Based on the tolerance spreadsheet, the proposed tolerances of 0.5 ppm for Squash/cucumber subgroup 9B is appropriate.Fluoxastrobin Summary of Analytical Chemistry and Residue Data DP#: 380846

Page 15 of 22 Table 10 . Tolerance Sum ma ry for Fluoxastrobin Commodity Tolerance (ppm) Comments; Correct Commodity Definition Established Proposed Recom mended 40 CFR §180.609(a)(1) Crop subgroup 9B Squash/Cucumbers -- 0.5 0.5 Squash/cucumber sub group 9B References DP#s: 292422 and 303256 Subject: Fluoxastrobin: Human Health Risk Assessment for Proposed Uses on Peanuts,

Tuberous and Corm Vegetables (Subgroup 1C), Leaf Petiole Vegetables (Subgroup 4B), Fruiting Vegetables (Group 8), Turf, and as a Seed Treatment on Potato (Seed Pieces), Peanut and Turf. PC Code: 028889. Petition No.: 3F6556. From: S. Winfield To: C. Giles - Parker Dated: 1/24/05 MRIDs: None DP#: 289106 Subject: PP#3F6556. Fluoxastrobin. Petition for the Establishment of Permanent

Tolerances for Use on Peanuts, Tuberous and Corm Vegetables Subgroup, Leaf Petiole Vegetables Subgroup, Fruiting Vegetables Group, and Seed Treatment of Peanut and Potato. First Food/Feed Use. Summary of Analy tical Chemistry

and Residue Data. From: W. Wassell To: D. McNeilly Dated: 1/25/05 MRIDs: 45865507 - 458655 34 and 45865601 - 458656 11 DP#: 334234 Subject: Fluoxastrobin . Supplemental Residue Data for Livestock Metabolism, Residue

Analy tical Methods, Storage Stability, Crop Field Trials, an d Rotational Crop Field Trials, Submitted to Fulfill Conditions of Registration for Fluoxastrobin 480 SC (EPA Reg. No. 66330 - 64 ) . From: A. Acierto To: J. Bazuin/T. Kish Dated: 10/30/08 MRIDs: 46486101 - 46486104 and 46925801 - 46925804Fluoxastrobin Summary of Analytical Chemistry and Residue Data DP#: 380846

Page 16 of 22 DP# s : 356953 and 35769 1 Subject: Fluoxastrobin : Petitions for the Establishment of Permanent Tolerances for New

Uses on L ow - Growing Berry Crop Subgroup 13 - 07G (PP# 8F7406) , Soy bean and Field Corn (PP#8F7437). Summary of Analy tical Chemistry

and Residue Data . From: M. Negussie To: T. Kish Dated: 07/08/09 MRIDs: 47494701 and 47549202 - 4754920 5 Attachments: International Residue Limit Status sheet Appendix I - Tolerance Assessment Calculations Template Version April 200 8Fluoxastrobin Summary of Analytical Chemistry and Residue Data DP#: 380846

Page 17 of 22 International Residue Limits. Summary of US and International Tolerances and Maximum Residue Limits Residue Definition : US Canada Mexico 2 Codex 3 40 CFR 180.609 Plant: fluoxastrobin, (1 E) - [2 - [[6 - (2 - chlorophenoxy) - 5 - fluoro - 4 - pyrimidinyl]oxy]phenyl](5,6 - dihydro - 1,4,2 - dioxazin - 3 - yl)methanone O - methyloxime and its Z isomer, (1 Z ) - [2 - [[6 - (2 - chlorophenoxy) - 5 - fluoro - 4 - pyrimidinyl]oxy]phenyl](5,6 - dihydro 1,4,2 - dioxazin - 3 - yl)methanone O - methyloxime Livestock: fluoxastrobin, (1E) - [2 - [[6 - (2 - chlor ophenoxy) - 5 - fluoro 4 - pyrimidinyl]oxy]phenyl](5,6 - dihydro - 1,4,2 - dioxazin - 3 - yl)methanone O - methyloxime, its Z isomer, (1 Z ) - [2 - [[6 - (2 - chlorophenoxy) - 5 - fluoro - 4 - pyrimidinyl]oxy]phenyl](5,6 - dihydro 1,4,2 - dioxazin - 3 - yl)methanone O - methyloxime, and its phenoxyhydroxypyrimidine, 6 - (2 - chlorophenoxy) - 5 - fluoro - 4 - pyrimidinol None None

Commodity 1 Tolerance (ppm) /Maximum Residue Limit (mg/kg) US Canada Mexico 2 Codex Squash/cucumber subgroup 9B 0.5

Completed: M. Negussie; 09/23/2010 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 measu red on the fat portion of the sample. MRLs indicated as proposed have not been finalized by the CCPR and the CAC.Fluoxastrobin Summary of Analytical Chemistry and Residue Data DP#: 380846

Page 18 of 22 Appendix I. Tolerance Assessment Calculations. For each of the crops listed below, the Guidance for Setting Pesticide Tolerances Based on F ield Trial Data ( SOP ) , along with the tolerance spreadsheet (August 2009 version) , was used for calculating recommended tolerances. As specified in the SOP, the minimum of the 95% upper confidence limit (UCL) on the 95 th percentile and the point estimate of the 99 th percentile was selected as the tolerance value in cases when the dataset was large (greater than 15 samples) and reasonably

lognormal. For datasets that were not lognormal, the upper bound on the 89 th percentile was selected as the tolerance v alue (distribution - free method). The rounding procedures specified in the SOP were also used. Cucumber The dataset used to establish tolerance s for combined residues of fluoxastrobin and its Z - isomer on cucumber consisted of field trial data representin g application rates of 0.68 - 0.73 lb ai/A ( 4 applications at 0. 1 7 - 0. 19 lb ai/A/application) with a 1 - day PHI . The field trial application rates and PHI s are in accordance with the label application rate and minimum label PHI , respectively . The residue values entered into the tolerance spreadsheet are provided in Table I - 1. All field trial sample results for cucumber and squash were above the LOQ (LOQ = 0.0 1 ppm). The datasets were small ( 12 and 10 samples, respectively ). Visual inspection of the lognorm al probability

plots (Figures I - 1 and I - 3 ) and the approximate Shapiro - Francia test statistic s (Figures I - 2 and I - 4 ) indicated that the datasets for cucumber and squash were reasonably lognormal. Using the tolerance spreadsheet, the recommended toleran ce for cucumber is 0.25 ppm and 0.5 ppm for squash. Because the minimum and maximum recommended tolerances differ by less than 5x, a crop group tolerance is appropriate for squash/cucumber subgroup 9B. The recommended value is 0.5 ppm, the maximum of the recommended individual tolerances , which is the same as the proposed tolerance (0. 5 ppm) . Table I - 1 . Residue data used to calculate tolerance s for f luoxastrobin on cucumber . Regulator: EPA EPA EPA Chemical: Fluoxastrobin Fluoxastrobin Fluoxastrobin Crop: Cucumber Cantaloupe Squash PHI: 1 - day 1 - day 1 - day App. Rate: 0. 68 - 0. 73 lb ai/A 0. 68 - 0. 71 lb ai/A 0. 68 - 0. 71 lb ai/A Submitter: Arysta LifeScience Arysta LifeScience Arysta LifeScience MRID Citation: MRID 48088301 MRID 48088301 MRID 48088301 Comb ined r esidues of fluoxastrobin and its Z - isom er (ppm) 0.06 0.09 0.10 0.09 0.08 0.12 0.04 0.19 0.07 0.05 0.09 0.05 0.10 0.34 0.11 0.08 0.34 0.18 0.18 0.88 0.04Fluoxastrobin Summary of Analytical Chemistry and Residue Data DP#: 380846

Page 19 of 22 Table I - 1 . Residue data used to calculate tolerance s for f luoxastrobin on cucumber . Regulator: EPA EPA EPA Chemical: Fluoxastrobin Fluoxastrobin Fluoxastrobin Crop: Cucumber Cantaloupe Squash PHI: 1 - day 1 - day 1 - day App. Rate: 0. 68 - 0. 73 lb ai/A 0. 68 - 0. 71 lb ai/A 0. 68 - 0. 71 lb ai/A Submitter: Arysta LifeScience Arysta LifeScience Arysta LifeScience MRID Citation: MRID 48088301 MRID 48088301 MRID 48088301 Comb ined r esidues of fluoxastrobin and its Z - isom er (ppm) 0.16 0.78 0.04 0.11 0.33 0.01 0.06 0.27 0.12 0.07 0.41 0.07 0.42 Figure I - 1 . Lognorm al probability plot of f luoxastrobin field trial data for cucumber . Lognormal Probability Plot

99.9 99 98 95 90 80 70 50 30 20 10 5 2 1 0.1 1.0000

0.5000

0.2500

0.1250

0.0625

0.0313 y = 0.466x - 2.5126 R 2 = 0.973

PercentilesConcentrations EPA Fluoxastrobin Cucumber 1 0.68-0.71 lb ai/A Arysta LifeScienceFluoxastrobin Summary of Analytical Chemistry and Residue Data DP#: 380846

Page 20 of 22 Figure I - 2 . Tolerance spreadsheet sum ma ry of f luoxastrobin field trial data for cucumber . Regulator: EPA Chemical: Fluoxastrobin Crop: Cucumber PHI: 1 App. Rate: 0.68-0.71 lb ai/A Submitter: Arysta LifeScience

n: 12 min: 0.04 max: 0.18 median: 0.08 average: 0.09 95th Percentile 99th Percentile 99.9th Percentile 0.20 0.20 0.25 (0.25) (0.30) (--) 0.20 0.25 0.35 (0.30) (0.45) (--) 0.25 0.25 0.50 0.9730 p-value > 0.05 : Do not reject lognormality assumption Approximate Shapiro-Francia Normality Test EU Method I Normal

UCLMedian95th 95/99 Rule EU Method II Distribution-Free Mean+3SDFluoxastrobin Summary of Analytical Chemistry and Residue Data DP#: 380846

Page 21 of 22 Figure I - 3 . Lognorm al probability plot of f luoxastrobin field trial data for summer squash. Lognormal Probability Plot

99.9 99 98 95 90 80 70 50 30 20 10 5 2 1 0.1 1.0000 0.5000 0.2500 0.1250 0.0625 0.0313 0.0156 0.0078 y = 0.8331x - 2.7163 R 2 = 0.8769

PercentilesConcentrations EPA Fluoxastrobin Summer squash 1 0.68-0.71 lb ai/A Arysta LifeScienceFluoxastrobin Summary of Analytical Chemistry and Residue Data DP#: 380846

Page 22 of 22 Figure I - 4 . Tolerance spreadsheet sum ma ry of f luoxastrobin field trial data for summer squash . Regulator: EPA Chemical: Fluoxastrobin Crop: Summer squash PHI: 1 App. Rate: 0.68-0.71 lb ai/A Submitter: Arysta LifeScience

n: 10 min: 0.01 max: 0.18 median: 0.09 average: 0.08 95th Percentile 99th Percentile 99.9th Percentile 0.20 0.25 0.25 (0.25) (0.30) (--) 0.30 0.50 0.90 (0.80) (1.9) (--) 0.25 0.25 0.60 0.8769 p-value > 0.05 : Do not reject lognormality assumption Approximate Shapiro-Francia Normality Test EU Method I Normal

UCLMedian95th 95/99 Rule EU Method II Distribution-Free Mean+3SD