Py

raclostrobin DP 410737

Page **1** of **22 UNITED STA** 

**TES ENVIRONMENTA L PROTECTION A** **GENCY WA** **SHINGTON, D.C. 20460 OFFICE OF CHEMICAL SAFETY**  **AND POLLUTION PREVENTION MEMORANDUM**  **Date :**  04/ 30 /2013 **SUBJECT: Pyraclostrobin**  **:** Petition for the Establishment of Permanent Tolerances and

Registration for Use on Belgi um Endive, Persimmon, and Globe Artichoke. Request for Crop Group Expan s ions/Revisions for Bulb Vegetable Group 3 - 07, Fruiting Vegetable 8 - 10, Citrus Fruit Group 10 - 10, Pome Fruit Group 11 - 10, Berry Subgroups 13 - 07A, B, F, and G, and Oilseed Group 20. Summary of Analy tical Chemistry

and Residue Data . **PC Code:** 099100 **DP Barcode:** D 410737 ,405065 **Decision No.:** 468304 **Registration No s**  **. :**  7969 - 18 7 ; 7969 - 1 99 ; 7969 - 186 ; 7969 - 289 **Petition No .:**  2F80 69 **Regulatory Action:** Section 3 Registration **Risk Assessment Type:** Single Chemical/Aggregate **Case No.:** N/A **T XR No.:**  N/A **CAS No.:** 175013 - 18 - 0 **MRID No s:**  48897401, 48897402, 48897403 **40 CFR:** 180.582 **FROM:** Stephen Funk , Senior Chemist

Risk Assessment Bran ch III (RAB I II) Health Effects Division (HED; 7509P) **THROUGH:** Christine Olinger, Branch Chief

Risk Assessment Branch III (RABIII) Health Effects Division ( HED; 7509P) **TO:** Barbara Madden

Andrew Ertman R egistration D ivision ( RD; 7505P) And Barry O’Keefe , Senior Biologist Risk Assessment Branch III (RABIII) Health Effects Division (HED; 7509P)Py

raclostrobin DP 410737

Page **2** of **22 Executive Summary**  Py raclostrobin, or methyl [2 - [[[1 - (4 - chlorophenyl) - 1 H - py razol - 3 - yl ]oxy]methyl] phenyl]methoxycar

bamate belongs to the strobilurin class of fungicides. The fungicide is currently registered to BASF Corporation (BASF) for use on a variety of field, vegetable, fruit, and nut crops. It is formulated as water - dispersible granules (WDG) or an emulsifiabl e concentrate (EC) and is ty pically applied as foliar applications using ground or aerial equipment at maximum seasonal rates of 0.3 - 3.0 lb ai/A. The 20% WDG formulation is also registered for use as a seed treatment on some crops. The Interregional Rese arch Project Number 4 ( IR - 4 ) is proposing new use s for py raclostrobin on globe artichoke, Belgian end ive , and persimmon and is requesting certain crop group conversions. The proposed use for persimmon and globe artichoke is up to three applications of a WG formulation with a seasonal maximum rate of 0. 55 lb ai/acre and a 0 day PHI . The proposed use for Belgium endive is a root treatment with a WG formulation with a total application rate of about 0.027 lb ai/1000 lbs of root. IR - 4 has proposed the es tablishment of a tolerance for the combined residue of the fungicide py raclostrobin (carbamic acid, [2 - [[[1 - (4 - chlorophenyl) - 1 H - py razol - 3 - yl ]oxy]methyl]phenyl]methoxy- , methyl ester) and its desmethoxy metabolite methyl -N

- [[[1 - (4 - chlorophenyl) py

razol - 3 - yl ]oxy]o - tolyl] carbamate, expressed as parent compound, in or on the following raw agricultural commodit ies :

Artichoke, globe ........................................ 3.0 ppm Endive, Belgium........................................3.0 ppm Persimmon...............................................3.0 ppm IR - 4 has also proposed updating th e existing crop groups to vegetable, bulb, group 3 - 07 at 0.9 ppm; vegetable, fruiting, group 8 - 10 at 1.4 ppm; fruit, citrus, group 10 - 10 at 2.0 ppm; fruit, pome, group 11 - 10 at 1.5 ppm; oilseed, group 20 at 0.45 ppm; caneberry subgroup 13 - 07A at 4.0 ppm; bushberry

subgroup 13 - 07B at 4.0 ppm; small fruit, vine climbing subgroup (except fuzzy kiwi) 13 - 07F at 2.0 ppm; and low growing berry subgroup 13 - 07G except cranberry at 1.2 ppm. IR - 4 has also proposed removing tolerances for berry , group 13 at 4.0 ppm; fruit, citrus, group 10 at 2.0 ppm; fruit, pome, group 11 at 1.5 ppm; grape at 2.0 ppm; strawberry at 1.2 ppm; vegetable, bulb, group 3 at 0.9 ppm; vegetable, fruiting, group 8 at 1.4 ppm; borage, seed at 0.45 ppm; castor oil plant, seed at 0.45 ppm; Chine se tallowtree, seed at 0.45 ppm; crambe, seed at 0.45 ppm; cuphea, seed at 0.45 ppm; echium, seed at 0.45 ppm; euphorbia, seed at 0.45 ppm; evening primrose, seed at 0.45 ppm; flax seed at 045 ppm; gold of pleasure, seed at 0.45 ppm; hare’s ear mustard, s eed at 0.45 ppm; jojoba, seed at 0.45 ppm; lesquerella, seed at 0.45 ppm; lunaria, seed at 0.45 ppm; meadowfoam, seed at 0.45 ppm; milkweed, seed at 0.45 ppm; mustard, seed at 0.45 ppm; niger seed, seed at 0.45 ppm; oil ra d ish, seed at 0.45 ppm; poppy , see d at 0.45 ppm; rapeseed, seed at 0.45 ppm; rose hip, seed at 0.45 ppm; safflower, seed at 0.45 ppm; stokes aster, seed ato 0.45 ppm; sunflower, seed at 0.45 ppm; sweet rocket, seed at 0.45 ppm; tallowwood, seed at 0.45 ppm; tea oil plant, seed ato 0.45 ppm ; and vernonia, seed at 0.45 ppm. T olerances have been established in 40 CFR §180.582 for residues of the fungicidePy

raclostrobin DP 410737

Page **3** of **22** py raclostrobin, including its metabolites and degradates. Compliance with the tolerance levels is to be determined by

measuring on ly the sum of py raclostrobin (carbamic acid, [2 - [[[1 - (4 - chlorophenyl) - 1 H

- py razol - 3 - yl ]oxy]methyl]phenyl]methoxy- , methyl ester) and its desmethoxy metabolite (methyl N

- [[[1 - (4 - chlorophenyl) - 1 H - py razol - 3 - yl ]oxy]methyl]phenyl carbamate), cal culated as the stoichiometric equivalent of py raclostrobin . The established tolerances for plant food commodities range from 0.02 ppm in/on wheat grain to 29 ppm in/on leafy vegetables, except Brassica . A Section 18 tolerance exists for Belgian endive. Tolerances for livestock commodities are listed in 40 CFR §180.582 (a)(2) and are expressed in terms of the combined residues of the fungicide py raclostrobin and its metabolites convertible to 1 - (4 - chlorophenyl) - 1 H - py razol - 3 - ol and 1 - (4 - chloro - 2 - hydroxy ph enyl) - 1 H

- py razol - 3 - ol, expressed as parent compound. The established tolerances for livestock commodities range from 0.1 to 1.5 ppm; no tolerances are established for poultry commodities. HED ( D278044, Metabolism Assessment Review Committee (MARC ) , 10/ 09/01 ) has determined that for purposes of tolerance and dietary risk assessments, the residues of concern in plant and rotational crop commodities include py raclostrobin and desmethoxy metabolite (BF 500 - 3) . The residues of concern in livestock commoditi es include py raclostrobin and its metabolites convertible to 1 - (4 - chlorophenyl) - 1 H - py razol - 3 - ol (BF 500 - 5) and 1 - (4 - chloro - 2 - hydroxy phenyl) - 1 H

- py razol - 3 - ol (BF 500 - 8) . There are adequate residue analy tical methods for tolerance enforcement. The analy tical methods for plant commodities are liquid chromatography with tandem mass spectro metry (LC/MS/MS ) and high pressure liquid chromatography with ultraviolet detector ( HPL C/UV) , which both measure py

raclostrobin and its desmethoxy metab olite. The analy

tical methods for livestock commodities , gas chromatography with mass spectro metry (GC/MS ) and LC/MS/MS, convert py

raclostrobin and related metabolites to chlorophenylpy razolol (BF 500 - 5) and hydroxylated chlorophenylpy razolol (BF 500 - 8) i n goats and chlorophenylpy razolol (BF 500 - 5) and a hydroxylated chlorophenylpy razolol isomer of BF 500 - 8 (BF 500 - 9) in poultry . Samples (artichoke, persimmon, Belgium endive ) were analy zed for py

raclostrobin and metabolite BF 500 - 3 using BASF Analy tical Method Number D9908 (Version 2) , " Method for Determining BAS 500 F, BF 500 - 3 and BAS 510 F Residues in Plant Matrices using LC /MS/MS." (MRID 4670001). T he lower limit of method validation (LLM V) in this study was 0.02 ppm for both py

raclostrobin and BF 50 0 - 3. The LC/MS/MS method used to determine residues of py

raclostrobin and BF 500 - 3 were adequately validated in conjunction with the field sample analyses. The average recovery of all py raclostrobin and BF 500 - 3 fortifications was adequate. The method i s adequate for data collection. The requirements for multiresidue methods testing data are fulfilled. Py raclostrobin was successfully

evaluated through several of the FDA protocols (complete recovery through protocols D and E), while recovery of metaboli te BF 500 - 3 was unsuccessful in all protocols. Samples of artichoke from field trials were stored frozen for up to 21 months prior to analysis. Samples of Belgium endive from field trials were stored frozen for up to 10 months. Sample s of persimmon from field trials were stored frozen for up to 18.4 months. Adequate storage stability data are available demonstrating that residues of py raclostrobin and its metabolite BF 500 - 3 arePy

raclostrobin DP 410737

Page **4** of **22** stable under frozen conditions in/on the representative crop commodities of grape juice, sugar beet tops and roots, tomatoes, and wheat grain and straw for up to 25 months, and in peanut nutmeat and processed oil fo r up to 19 months (DP 269668, L. Cheng, 11/28/01). These data are adequate to support the storage conditions and durations of samples from the submitted field trials. There are no feed commodities associated with persimmon, artichoke, or Belgium endive. Therefore, the livestock diets are not impacted, and the existing livestock commodity tolerances remain adequate. IR - 4 has submitted field trial data for three trials each for py raclostrob in in persimmon, in Belgium endive, and in globe artichoke in the USA. At each persimmon and artichoke trial location, the treated plots received three foliar directed applications o f a 12.8% WDG formulation (Pristine ® ) of py raclostrobin at 0.19 lb ai/A, for a total application rate of 0.55 lb ai/A. The retreatment interval was 6

– 8 days. Applications were made using ground equipment in spray volumes of 10 - 75 gal/acre for artichok e and 55

– 97 gal/acre for persimmon. Maturing commodities were present. No adjuvants were used. Samples of mature commodities were taken at a PHI

of 0 days. For Belgium endive (witloof chicory ), two applications were made with a 12.8% WDG formulation (Pristine ® ) of py raclostrobin . The first was a broadcast application to dormant chicory roots at a rate of 0.58 g ai/100 lbs of root. The second was a broadcast application to roots packed in forcing trays at budding stage at a rate of 0.092 g ai/ft2 o r 8.8 lb ai/ acre. The PHIwas 17 - 19 days for the pre - forcing application. R esidues (and per trial averages) of py raclostrobin, BF 500 - 3, and combined py raclostrobin and BF 500 - 3 in/on artichoke flower heads harvested at a 0 - day PHIwere 0.514 - 1.110 (0. 618 - 1.045), <0.02 - 0.056 (<0.02 - 0.056), and <0.534 - 1.166 (<0.638 - 1.101) ppm, respectively . R esidues (and per trial averages) of py

raclostrobin, BF 500 - 3, and combined py raclostrobin and BF 500 - 3 in/on persimmon fruit harvested at a 0 - day PHIwere 0.421 - 1.2 78 (0.092 - 1.155), <0.02 - 0.077 (<0.02 - 0.073), and <0.103 - 1.355 (<0.112 - 1.228) ppm, respectively . Following a broadcast application of the 12.9% WDG formulation of py raclostrobin to post - dormancy chicory roots in packing trays, applied just before forcing b egan, at 0.089 - 0.097 g ai/ft2 (treatment 03), residues (and per trial averages) of py

raclostrobin and of combined py raclostrobin and BF 500 - 3 in/on endive heads harvested at PHI s of 17 - 19 - days were 0.1239 - 1.7620 (0.150 - 1.347) and <0.144 - <1.782 (<0.170 - <1.3 67) ppm, respectively . Residues were lower from a combined treatment of a single broadcast application of the same formulation to dormant chicory roots at 0.584 - 0.591 g ai/100 lb of roots, followed by

a broadcast application of the same formulation to pos t - dormancy chicory roots in packing trays, applied just before forcing began at 0.092 - 0.101 g ai/ft2

. Analy tical reference standards for py raclostrobin and its regulated metabolites are available at the EPA National Pesticide Standards Repository . Adequ ate confined, limited and extensive field rotational crop studies are available supporting the existing tolerances for indirect residues of py raclostrobin in rotational crops. These data support the 14 - day

plant - back interval currently specified for crops without py raclostrobin uses. No additional rotational crop data are required for purposes of this petition.Py

raclostrobin DP 410737

Page **5** of **22 Regulatory Recommendations and Residue Chemistry Deficiencies**  HED has examined the residue chemistry database for py

raclostrobin , and there ar e no residue chemistry deficiencies that would preclude granting Section 3 registration for the requested crop commodity use s of py

raclostrobin, or establishment of tolerances for residues of py raclostrobin. Itis recommended that a tolerance be establish ed for residues of the fungicide py raclostrobin, including its metabolites and degradates, in or on globe artichoke at 3.0 ppm, in or on persimmon at 3.0 ppm, and in or o n Belgium endive at 4 . 0 ppm . Compliance with the tolerance levels is to be determined by

measuring only

the sum of py

raclostrobin (carbamic acid, [2 - [[[1 - (4 - chlorophenyl) - 1 H

- py razol - 3 - yl ]oxy]methyl]phenyl]methoxy- , methyl ester) and its desmethoxy metabolite (methyl N

- [[[1 - (4 - chlorophenyl) - 1 H - py razol - 3 - yl ]oxy]methyl]phenyl carbamate), cal culated as the stoichiometric equivalent of py raclostrobin . The proposed updating of certain existing crop groups and the removal of certain oilseed tolerances and certain previous crop group /subgroup tolerances are acceptable. However, an additional o ilseed tolerance will need to be removed, and IR - 4 should r equest the following removal: cotton undelinted cotton seed (0.3 ppm). The Section 18 tolerance for Belgian endive should be removed concurrent with the establishment of the Section 3 tolerance for Belgium endive See Table 7 for details of the recommendations. A human health risk assessment is forthcoming. 860.1200 Direction for Use The proposed labels for Reg. No. 7969 - 199 (Pristine® fungicide), and 7969 - 187(Cabrio® EG fungicide) provide directions for use on the low growing berry subgroup. Cranberry

must be removed from the list of crops. The title “low growing berry subgroup” should be changed to “low growing berry

subgroup except cranberry .” 860.15 50 Proposed Tolerances The availabl e data for Belgium endive will not support a tolerance level of 3.0 ppm. A revised Section F should be submitted with a tolerance for endive, Belgium at 4.0 ppm . The existing tolerance for undelinted cottonseed seed should be removed as it is replaced by the proposed and recommended tolerance for oilseed group 20. See Table 7. **Background** Py raclostrobin belongs to the strobilurin class of fungicides. Strobilurins are sy nthetic analogs of a natural antifungal substance which inhibits spore germination and mycelial growth and sporulation of the fungus on the leaf surface. T he chemical structure and nomenclature of py racl ostrobin are presented in Tabl e 1. The physicochemical properties of the technical grade of py raclostrobin are presented in Table 2 .Py

raclostrobin DP 410737

Page **6** of **22 TABLE 1.**  **Test Com pound Nom**  **enclature.** Compound

N N Cl O N O C H 3 O OCH 3 Common name Py raclostrobin Company experimental name BAS 500 F IUPAC name methyl 2 - [1 - (4 - chlorophenyl)pyrazol - 3 - yloxymethyl] -N - methoxycarb anilate CAS name methyl N - [2 - [[[1 - (4 - chlorophenyl) - 1 H - pyrazol - 3 - yl]oxy]methyl]phenyl] -Nmethoxycarbamate CAS registry number 175013 - 18 - 0 End - use product (EP) Headline® EC Fungicide , EPA Reg. No. 7969 - 186. Cabrio® EG fungicide, EPA Reg. No. 7969 - 187 Pristine® fungicide, EPA Reg. No. 7969 - 199 ,Headline® SC fungicide, EP A Reg. No 7969 - 289 **TABLE 2**  **. Physicochem** **ical Properties of Technical Grade Pyraclostrobin.** Parameter Value References 1 (MRID) Melting point/range 63.7 - 65.2oC 45118213 pH Not applicable Density 1.367 g/cm3 4511821 4 Water solubility at 20 oC 1.9 ± 0.17 mg/L (deionized water, pH 5.8) 451182 3 3 Solvent solubility n - heptane (0.37 g/100mL); 2 - propanol (3.0 g/100mL); 1 - octanol (2.42 g/100mL); olive oil (2.80 g/100m/L); methanol (10.08 g/100mL); >50 g/100mL in acetone, ethyl acetate , acetonitrile, dichloromethane and toluene. 451182 28 Vapor pressure 2.6 x 10 - 10 hPa at 20 oC 4511821 4 Dissociation constant, pKa None (no dissociable moieties) Octanol/water partition coefficient, Log(KOW) at room temperature 3.990 mean log Pow; Pow is 9772 45118 21 5 UV/visible absorption spectrum The structural identity of BAS 500 F was confirmed by NMR and MS spectra. UV molecular extinction (e [1 mol - 1 cm- 1 ]): 2.5x10 4 at 205 nm; 2.4x10 4 at 275 nm. 1996/10955 2

1 Product Chemistry data were reviewed by the Regis tration Division (D P# 269848 and D P# 274191, 5/3/01, 5/15/01, and 6/7/01, S. Malak) . 2 BASF Document Number. **860.1200 Directions for Use** Py

raclostrobin DP 410737

Page **7** of **22** Proposed supplemental labels were provided for end use products 7969 - 186 (Headline® Fungicide) , 7969 - 187 (Cabrio® EG fungicide) , 7969 - 199 (Pristine® fungicide) , and 7969 - 289 (Headline® SC fungicide) . Only Pristine® fungicide is proposed for use on globe artichoke, persimmon, and Belgium endive. The remaining labels are associated with crop group conversions. Pristi ne® contains two active ingredients, py raclostrobin and boscalid. Only py raclostrobin is considered in this document; boscalid is being evaluated separately . **TABLE 3**  **. Sum ma**  **ry of Proposed Use Patterns of Pyraclostrobin**  **.** Applic. Timing, Ty pe, 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

**Globe Artichoke** Foliar with ground equipment, aerial equipment , or sprinkler irrigation 12.8%

P ristine® WG 7969 - 1 99 0.148 - 0.1 84 3 0.55 0 Apply at 7 - 14 day intervals **Belgium Endive** 

Root spray - (1)Pre - cold storage (2) Forcing 12.8%

Pristine® WG 7969 - 199 (1 ) 0.0064

–

0. 0128 lb ai/1000 lbs root (2) 0.0072

– 0.0144 lb ai/70 square feet forcing tray [ 4.4

– 8. 9 lb s ai/acre] 1 0.0272 lb ai/1000 lbs root (approximate) 19 Make one application (1 ) to the roots when brought into cold storage prior to forcing. Apply in 3.0 to 3.5 gals of water per 1000 lbs. root. Make a second application (2) at the beginni ng of forcing after the roots have been packed into forcing trays. Apply in about 100 fl ozs water per 70 square feet of forcing tray. A 70 square feet forcing tray contains approximately 1000 lbs of roots. Do not apply after the beginning of forcing. **Pe rsim**  **mo n**  Foliar with ground equipment, aerial equipment, or sprinkler irrigation 12.8%

Pristine® WG 7969 - 199 0.148

–

0.184 3 0.55 0 Apply at 7 - 14 day intervals The proposed labels end use products7969 - 186 (Headline® Fungicide), 7969 - 187(Cabrio® EG fungi cide) , 7969 - 199 (Pristine® fungicide), and 7969 - 289 (Headline® SC fungicide) include changes for crop group/subgroup conversions.

. Conclusion s: The submitted use directions are sufficient to allow for evaluation of the submitted residue data relative to the proposed use pattern for persimmon, Belgium endive, and globe artichoke. The proposed label changes related to crop group/subgroup conversions are acceptable.Py

raclostrobin DP 410737

Page **8** of **22 860.1300 Nature of the Residue**  **- Plants**  HED M ARC , DP# 278044 , L. Cheng , 10/9/01 PP#0F61 39, DP# 269668 , L. Cheng , 11/28/01 Adequate metabolism studies with py raclostrobin on grapes, potatoes, and wheat have been reviewed (D269668, 11/28/01, L . Cheng) in conjunction with PP#0F06139. The results of these studies indicate that the metabolism o f py raclostrobin is similar in the three crops investigated. The HED Metabolism Assessment Review Committee (MARC) discussed the results of these studies on 9/20/01, and concluded that the nature of the residue in plants is understood. For the purpose of tolerance and risk assessment, the terminal residues of concern in plants consist of py raclostrobin and its desmethoxy metabolite (BF 500 - 3). **860.1300 Nature of the Residue –**  **Livestock** HED M ARC , DP# 278044, L. Cheng, 10/9/01 PP#0F6139, DP# 269668, L. Ch eng, 11/28/01 The nature of the residue in livestock is adequately understood based on acceptable ruminant and poultry metabolism studies. In goat , the major residues are py raclostrobin and BF 500 - 3 in muscle and fat; py

raclostrobin, BF 500 - 3, and BF 500 - 5 and its sulfate conjugate in milk; py raclostrobin, BF 500 - 3, and BF 500 - 5 and its sulfate conjugate, and hydroxylated desmethoxy metabolite (500M67) in kidney ; and metabolites hydroly zed to BF 500 - 5 and its hydroxylated compound (BF 500 - 8) in liver. In poultry , the major residues are py raclostrobin and BF 500 - 3 in eggs; py raclostrobin, BF 500 - 3, and hydroxylated BF 500 - 3 (500M64) in fat; and the glucuronic acid conjugate of hydroxylated BF 500 - 3 (500M32) in liver. Radioactive residues were below detect ion in muscle. The main degradation reactions in livestock consist of demethoxy lation, hydroxylation, and conjugation, and breaking of the ether bond. HED has determined that for the tolerance and risk assessment, the residues of concern in livestock co mmodities consist of py raclostrobin and its metabolites convertible to 1 - (4 - chlorophenyl) - 1 H

- py razol - 3 - ol (BF 500 - 5) and 1 - (4 - chloro - 2 - hydroxy phenyl) - 1 H

- py razol - 3 - ol (BF 500 - 8). **860.1340 Residue Analytical Methods** PP#0F6139 , DP# 269668 , L. Cheng , 11/28/01 PP#0F6139, DP# 269850 , L. Cheng , 11/8/00 MRID: 48049201, W. Cutchin, in process Enforcement : Two adequate methods are available for enforc ement purposes for residues of py raclostrobin and the metabolite BF 500 - 3 in/on plant commodi ties: an LC/MS/MS meth od (BASF Method D9 9 08) and an HPL C/UV method (Method D9904). The validated method L OQ for both py

raclostrobin and BF 500 - 3 is 0.02 ppm in all tested plant matrices, for a combined LOQ of 0.04 ppm. Adequate independent method validation and radiovalidatio n data were submitted for both methods and forwarded to Analy tical Chemistry

Branch/Biological and EconomicAnalysis Division ( ACB/BEAD ) for a petition method validation. Data Collection: Samples from field trial studies were analy zed for py

raclostrobin and its metabolite BF 500 - 3 using BASF Analy tical Method Number D9908, "Method for DeterminingPy

raclostrobin DP 410737

Page **9** of **22** BAS 500 F, BF 500 - 3 and BAS 510 F Residues in Plant Matrices using L C/MS/MS." Briefly , residues of py

raclostrobin and BF 500 - 3 were extracted from the commodity samples with a 70:25:5 methanol/water/2 N HCI mixture. An aliquot of the extract was removed and cleaned by liquid/liquid partition with cyclohexane and 1N HCl saturated with NaCl. An aliquot of the cyclohexane phase was taken, evaporated to dry ness, and re - dissolved in a buffered methanol:water (80:20, v :v, each containing 0.1% formic acid and 4 mM ammonium formate) for analysis by

L C/MS/MS. The final chromatographic analysis of residues was determined by MS/MS detection using the positive ionization mod e monitored ion transitions from m/z 388 →194 for py

raclostrobin and m/z 358 →164 for BF 500 - 3. The LLMV in the studies was 0.02 ppm for each of py raclostrobin and BF 500 - 3. Concurrent recovery experiments were conducted at spiking levels of 0.02 ppm and 2.0 ppm for each of py raclostrobin an d its metabolite BF - 500 - 3. Concurrent recoveries from fortifications of artichoke ranged from 73 98% for py raclostrobin and from 70

– 101% for BF - 500 - 3. Concurrent recoveries from fortifications of Belgium endive ranged from 78

– 97% for py raclostrboin and from 86

– 97% for BF - 500 - 3. Concurrent recoveries from fortifications of persimmon ranged from 76

– 97% for py

raclostrobin and from 73

– 89% for BF - 500 - 3. Conclusion s: There are adequate residue analy tical methods for tolerance enforcement and dat a collection. **860.1360 Multiresidue Methods** PP#0F6139 , DP# 269668 , L. Cheng , 11/28/01 Py raclostrobin was successfully evaluated through several of the FDA protocols, while recovery of BF 500 - 3 was unsuccessful in all protocols. Py raclostrobin was compl etely recovered through Protocol D (in grape) and E (in grape), and partially recovered through Protocol F (in peanut). Metabolite BF 500 - 3 had poor peak shape and inadequate sensitivity with Protocol C columns, and therefore, was not further analy zed und er Protocol D, E, and F. The results of the multiresidue testing for py raclostrobin were forwarded to FDA on 1/4/02 for the purpose of updating the Pesticide Analytical Manual , Volume I ( PAM I) . **860.1380 Storage Stability** PP#0F6139 , DP# 269668 , L. Cheng , 11/28/01 Artichoke s amples were stored frozen at < - 5 °C from collection to extraction for 628 - 644 days (20.6 - 21.2 months). Samples were analy zed within 0 - 1 days of extraction. Belgium endive s amples were stored frozen ( generally < - 5 °C ) from collection to extraction for 290 - 304 days (9.5 - 10.0 months). Samples were analy zed within 0 - 2 days of extraction. Persimmon s amples were stored frozen at < - 5 °C from collection to extraction for 532 - 560 days (17.5 - 18.4 months). Samples were analy

zed within 0 - 1 days of extraction Adequate storage stability data are available demonstrating that residues of py raclostrobin and its metabolite BF 500 - 3 are stable under frozen conditions in/on fortified samples of grape juice, sugar beet tops and roots, tomatoes, and wheat grain and straw for up to 25 months, and in/on fortified samples of peanut nutmeat and processed oil for up to 19 months. It was concluded that the plant commodities chosen for the storage stability study were representative of all crops: an oilseed (peanut nutmeat), a non - oily

grain (wheat grain), a leafy vegetable (sugar beet tops), a root crop (sugarPy

raclostrobin DP 410737

Page **10** of **22** beet roots), a fruit/fruiting vegetable (tomatoes), a dry feed (wheat straw), and processed oil (peanut) and juice (grape) commodities (DP#s 269668 etc . , L . Cheng, 11/28/01). These data are adequate to support the storage conditions and durations of samples from the submitted field trials. Conclusion s: T hese data are adequate to support the storage conditions and durations of samples from the articho ke, persimmon, and Belgium endive studies. No correction to residue values for loss during storage are necessary . **860.1400 Water, Fish, and Irrigated Crops** This guideline requirement is not relevant to the current petition s as there are no aquatic uses being proposed for py

raclostrobin. **860.1460 Food Handling** This guideline requirement is not relevant to the current petition s as there are no food - handling uses being proposed for py raclostrobin. **860.1480 Meat, Milk, Poultry, and Eggs** There are no feed items associated with the requested new uses (artichoke, Belgium endive, persimmon). The replacement of individual oilseed tolerances with the oil seed crop group 20 tolerance effectively

raise s the tolerance of undelinted cotton seed from 0.3 to 0.45 pp m. This will have no effect on the calculated diets of livestock, which are based on high residues from the field trials and processing studies. Therefore, no new considerations are required for residues in meat, milk, poultry , and eggs. **860.1500 Crop Field Trials**  MRID s: 48897401 - 48897403 Artichoke, Globe A total of 3 crop field trials on artichoke (globe) were conducted in the United S tates during the 2006 growing season in the North American Free Trade Agreement (NAFTA ) Growing Zone 10 (CA). Eac h trial consisted of one untreated (control) plot and one treated plot. At each trial location, the treated plots received three foliar directed applications of the 12.8% WDG formulation of py

raclostrobin (Pristine ® ) during the producing growth stage at rates of 0.178 - 0.188 lb ai/A/application (0.199 - 0.211 kg ai/ha/application), for total seasonal rates of 0.549 - 0.562 lb ai/A (0.615 - 0.630 kg ai/ha). Retreatment intervals ( RTI s ) were 6 - 8 days. Applications were made using backpack sprayers, with CO 2 as th e propellant, in spray volumes of 10 - 75 gal/A of water (94 - 702 L/ha), without any adjuvant. Samples of mature artichoke buds were harvested after the spray

had dried following the final application, reflecting a PHI of 0 days. Following three foliar di rected applications of the 12.8% WDG formulation of py raclostrobin at total rates of 0.549 - 0.562 lb ai/A, residues (and per trial averages) of py raclostrobin, BF 500 - 3, and combined py

raclostrobin and BF 500 - 3 in/on artichoke flower heads harvested at a 0 - dayPy

raclostrobin DP 410737

Page **11** of **22** PHIwere 0.514 - 1.110 (0.618 - 1.045), <0.02 - 0.056 (<0.02 - 0.056), and <0.534 - 1.166 (<0.638 - 1.101) ppm, respectively . Results are summarized in Table 4 . **TABLE 4**  **. Summary of Residue Data from**  **Globe Artichoke Crop Field Trials with Pyraclostrobin.**  Commodity Total Applic.

Rate (lb ai/A) [kg ai/ha] PHI

(days) Analyte Residue Levels 1 (ppm) n Sample Min. Sample

Max. LAFT 2 HAFT 2 Median Mean Std. Dev. Artichoke Flower Head 0.549 - 0.562

(0.615 - 0.630) 0 Py raclostro bin 3 0.514 1.110 0.618 1.045 0.759 0.807 0.218 BF 500 - 3 3 <0.02 0.0 56 <0.02 0.056 <0.02 8 <0.0 35 0.0 19 Combined 3 <0. 534 1.166 <0. 638 1.101 <0. 787 <0. 842 0. 236 1 Except for sample min/max, values reflect per trial averages; n = no. of field trials. For calculation of median, mean, and standard deviation, the LLMV (0.02 ppm) was used for any results reported as <LLMV in Table C.3. 2 LAFT = lowest average field trial; HAFT = highest average field trial. Conclusions: The number and geographic distribution of the trials are adequate. The analy tical method was demonstrated to be acceptable via concurrent recoveries of fortified control samples. The intervals of frozen storage of samples are covered by previous storage stability studies, and no corrections for loss of residue are neede d. The trials were conducted according to the proposed label for the WG formulation (single and seasonal application rates, PHI). The results of the field trials are acceptable for estimation of a n artichoke tolerance and for dietary risk assessment purp oses. Belgium endive (witloof chicory ) A total of 3 crop field trials on endive were conducted in the United States during the 2008 growing season in NAFTA Growing Zone 10 (CA). Endive is not grown in plots; all treatments occurred indoors. The produ ction of Belgium endive requires the growing of a crop of chicory plants in the field, harvesting the roots, and placing the chicory roots in cold storage to break dormancy , which can occur in as little as one week. After dormancy is broken, the roots are packed in a tray standing vertically , and the tray is placed in a forcing room, which is dark, cool and moist. Belgium endive heads then develop on the roots within approximately

17 to 19 days. Each trial for this study

consisted of one untreated (control) group (treatment 01) and three separate treatment groups (treatments 02, 03, and 04). Broadcast spray applications were made in two different ways. In Treatment 02, dormant roots (before being placed into cold storage) were sprayed as they

passed by the sprayer on a conveyer belt. For this treatment, the rate of application was reported as the amount of product applied per pound of roots. I n Treatment 03, roots were sprayed after they had been broken from dormancy , removed from cold storage, and pac ked vertically

into forcing trays. After they were sprayed, they

were placed into a forcing room. For this treatment, the rate of application was reported as the amount of product appliedPy

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Page **12** of **22** per ft2 of sprayed trays. Treatment 04 was a combination of the treatment 02 and 03 scenarios. All applications were made using a 12.9% water dispersible granule (WDG) formulation of py raclostrobin (Pristine ® ). Samples of mature endive heads were harvested at preharvest intervals (PHI s) of 25 - 27 days for treatment 02 and of 17 - 19 days for treatments 03 and 04. Following a single broadcast application of a 12.9% WDG formulation of py raclostrobin to dormant chicory

roots at 0.578 - 0.597 g ai/100 lb of roots (treatment 02), residues (and per trial averages) of py

raclostrobin and of combined py raclostrobin and BF 500 - 3 in/on endive heads harvested at PHI s of 25 - 27 - days were <0.02 - 0.0679 (<0.023 - 0.059) and <0.04 - <0.088 (<0.043 - <0.079) ppm, respectively . Following a broadcast application of the same formulation to post dorm ancy chicory roots in packing trays, applied just before forcing began, at 0.089 - 0.097 g ai/ft2 (treatment 03), residues (and per trial averages) of py raclostrobin and of combined py raclostrobin and BF 500 - 3 in/on endive heads harvested at PHI s of 17 - 19 - days were 0.1239 - 1.7620 (0.150 - 1.347) and <0.144 - <1.782 (<0.170 - <1.367) ppm, respectively . Following the combined treatment (treatment 04) of a single broadcast application of the same formulation to dormant chicory roots at 0.584 - 0.591 g ai/100 lb of roots , followed by a broadcast application of the same formulation to post - dormancy chicory roots in packing trays, applied just before forcing began, at 0.092 - 0.101 g ai/ft2 , residues (and per trial averages) of py raclostrobin and of combined py raclostrobin an d BF 500 - 3 in/on endive heads harvested at PHI s of 17 - 19 - days were 0.2250 - 0.8710 (0.256 - 0.771) and <0.245 - <0.891 (<0.276 - <0.791) ppm, respectively . No residues of metabolite BF 500 - 3 were found at or above the LLMV (0.02 ppm) in/on endive heads harvested following any

of the three treatments. The results are summarized in Table 5.Py

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Page **13** of **22 TABLE**  **5 Summary o**  **f Residue Data from Belgium** **Endive Crop Field Trials with Pyraclostrobin.**  Com modity Rate 1 PHI (days) Analyte Residue Levels 2 (ppm) n Sample Min. Sample

Max. LAFT 3 HAFT 3 Median Mean Std. Dev. **Treatm ent 02: One pre**  **- cold**  **- storage application**  **to roots**  Belgium endive heads 0.578 - 0.597 g

ai/100 lb of roots 25 - 27 Py

raclostro bin 3 <0.02 0.0679 <0.023 0.059 <0.040 <0.041 0.018 BF 500 - 3 3 <0.02 <0.02 <0.02 < 0.02 <0.02 <0.02 N/A Combined 3 <0.04 <0.088 <0.043 <0.079 <0.06 <0.061 0.018 **Treatm ent 03: One pre**  **- forcing application**  **to roots in packing tray**  Belgium endive heads 0.089 - 0.097 g

ai/ft2 17 - 19 Py

raclostro bin 3 0.1239 1.7620 0.150 1.347 0.900 0.799 0 .605 BF 500 - 3 3 <0.02 <0.02 <0.02 <0.02 <0.02 <0.02 N/A Combined 3 <0.144 <1.782 <0.170 <1.367 <0.920 0.819 0.605 **Treatm ent 04: One pre**  **- cold**  **- storage application**  **to roots + One pre**  **- forcing application**  **to roots in packing tray**  Belgium endive heads 0.584 - 0.591 g

ai/100 lb of roots **and** 3 0.092 - 0.101 g ai/ft2 17 - 19 Py

raclostro bin 3 0.2250 0.8710 0.256 0.771 0.551 0.526 0.258 BF 500 - 3 3 <0.02 <0.02 <0.02 <0.02 <0.02 <0.02 N/A Combined 3 <0.245 <0.891 <0.276 <0.791 <0.571 <0.546 0.258 1 Rate fo r pyraclostrobin , as calculated by the study reviewer based on the certificate of analysis of applied product in the study report. 2 Except for sample min/max, values reflect per trial averages; n = no. of field trials. For calculation of median, mean, a nd standard deviation, the LLMV (0.02 ppm) was used for any results reported as <LLMV in Table C.3. N/A = Not Applicable. 3 LAFT = lowest average field trial; HAFT = highest average field trial. Conclusions: The number and geographic distribution of the trials are adequate. The analy tical method was demonstrated to be acceptable via concurrent recoveries of fortified control samples. The intervals of frozen storage of samples are covered by previous storage stability studies, and no corrections for loss of residue are needed. The trials were conducted according to the proposed label for the WG formulation (single and seasonal application rates, PHI). The trials were pre forcing stage treatment only (treatment 3) yielded commodities with higher re sidues than the combined pre - cold storage treatment and pre - forcing stage treatment (treatment 4). The results of the field trials are acceptable for estimation of a Belgium endive tolerance and for dietary risk assessment purposes. Persimm on A total of 3 crop field trials on persimmon were conducted in the United States during the 2006 growing season in North American Free Trade Agreement (NAFTA) Growing Zones 3 (FL), 10 (CA), and 1 3 (HI). Each trial consisted of one untreated (control) plot and one treated plot. At each trial location, the treated plots received three foliar directed applications of the 12.8% water dispersible granule ( WDG ) formulation of py raclostrobin (Pristine ® ) during the fruiting stage at rates of 0.185 - 0.199 lb ai/A/applicatio n (0.207 - 0.223 kg ai/ha/application), for total seasonal rates of 0.564 - 0.573 lbPy

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Page **14** of **22** ai/A (0.632 - 0.642 kg ai/ha). Retreatment intervals (RTI s) were 7 - 8 days. Applications were made using a backpack sprayer, a tractor - mounted sprayer, or a Mistblower sprayer in spray volumes of 55 - 97 gal/A of water (514 - 907 L/ha), without any adjuvant. Samples of commercially

mature persimmon fruit were harvested after the spray had dried following the final application, reflecting a preharvest interval (PHI) of 0 days. Fol lowing three foliar directed applications of the 12.8% WDG formulation of py raclostrobin at total rates of 0.564 - 0.573 lb ai/A, residues (and per trial averages) of py raclostrobin, BF 500 - 3, and combined py

raclostrobin and BF 500 - 3 in/on persimmon fruit harvested at a 0 - day PHIwere 0.421 - 1.278 (0.092 - 1.155), <0.02 - 0.077 (<0.02 - 0.073), and <0.103 - 1.355 (<0.112 - 1.228) ppm, respectively . There was no residue decline study . Results are summarized in Table 6 . **TABLE 6**  **. Summary of Residue Data from**  **Persim mo**  **n C**  **rop Field Trials with Pyraclostrobin.** Commodity Total Applic.

Rate (lb ai/A) [kg ai/ha] PHI

(days) Analyte Residue Levels 1 (ppm) n Sample Min. Sample

Max. LAFT 2 HAFT 2 Median Mean Std. Dev. Persimmon Fruit 0.564 - 0.573

(0.6 32 - 0.6 42 ) 0 Py raclostro bin 3 0.421 1.278 0.092 1.155 0.437 0.561 0.542 BF 500 - 3 3 <0.02 0.077 <0.02 0.073 <0.02 <0.038 0.031 Combined 3 <0.103 1.355 <0.112 1.228 <0.457 <0.599 0.571 1 Except for sample min/max, values reflect per trial averages; n = no. of field trials. F or calculation of median, mean, and standard deviation, the LLMV (0.02 ppm) was used for any results reported as <LLMV in Table C.3. N/A = Not Applicable. 2 LAFT = lowest average field trial; HAFT = highest average field trial. Conclusions: The numbe r and geographic distribution of the trials are adequate. The analy tical method was demonstrated to be acceptable via concurrent recoveries of fortified control samples. The intervals of frozen storage of samples are covered by previous storage stability studies, and no corrections for loss of residue are needed. The trials were conducted according to the proposed label for the WG formulation (single and seasonal application rates, PHI). The results of the field trials are acceptable for estimation of a persimmon tolerance and for dietary risk assessment purposes. **860.1520 Processed Food and Feed** PP#0F6139, DP# 269668, L. Cheng, 11/28/01 MRID 48237401 No processing studies were submitted. None are necessary for persimmon, globe artichoke, or Belgium e ndive (witloof chicory ). **860.1650 Submittal of Analytical Reference Standards** Analy tical standards for py

raclostrobin and regulated metabolites (BF 500 - 3 ; BF 500 - 5; BF 500 - 8 ) are currently

available in the EPA Nationa l Pesticide Standards Repository (e - m ail correspondence with T. Cole , 01/14/2013 ) .Py

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Page **15** of **22 860.1850 Confined Accumulation in Rotational Crops**  MARC , DP# 278044 , L. Cheng , 10/9/01 PP#0F6139, DP# 269668, L. Cheng , 11/28/01 An adequate confined rotational crop study was reviewed in PP#0F6139. The study showed that the metabolism of py

raclostrobin in rotated crops is similar but more extensive than that in primary crops. Py

raclostrobin undergoes demethoxylation to yield BF 500 - 3, followed by further degradation to medium polar and polar metabolites, and subsequent conjugation reactions and incorporation into natural products. The HED MARC has determined that the residues of concern in rotational crops consist of py raclostrobin and metabolite BF 500 - 3. **860.1900 Field Accumulation in Rotational Crops** PP#0F6139 , DP# 269668, L. Cheng , 11/28/01 A limited field rotational crop study was reviewed in PP#0F6139. The results indicate that r esidues of py

raclostrobin and its metabolite BF 500 - 3 were each less than the method L OQ (<0.02 pp m) in/on rotational crop matrices (radish, roots and tops; cabbage, with and without wrapper leaves; and wheat forage, hay , and grain) planted 14 days following the last of six sequential foliar applications to the primary crop, cucumbers, of the 2 lb/gal EC formulation at 0.19 - 0.20 lb ai/A/application. Residues of py raclostrobin in/on one sample of wheat straw from the CA test site were at the L OQ (0.02 ppm), but residues of py raclostrobin in/on a replicate sample from the same plot were below the L OQ ( 0.012 ppm) for an average residue of <0.02 ppm. Residues of metabolite BF 500 - 3 were nondetectable (<0.02 ppm) in/on all samples of wheat straw. The registered py

raclostrobin end - use product labels presently specify a 14 - day plantback interval restrictio n for all crops that are not registered. **860.1550 Proposed Tolerances**Py

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Page **16** of **22** For the use of py

raclostrobin on globe artichoke, Belgium endive, and persimmon, tolerances are required . Based on evaluation of the field trial data with the Organization of Econo mic Cooperation and Development (OECD) tolerance calculation procedure (Appendix I), the tolerances listed in Table 7 are appropriate. Codex MRL s have been established for py raclostrobin in/on globe artichoke at 2 ppm. The recommended US tolerance is 3 p pm. Residue definitions are different in the US and in Codex, and the US tolerance is based on application of the OECD calculation procedure to the validated field trial data. The tolerance cannot be lowered to the Codex level as this could result in app arent violations for crops treated in accordance with the label. Canada does not have py raclostrobin tolerances for globe artichoke, Belgium endive, or persimmon. Therefore, there is no issue of harmonization with Canada. Several crop group conversion s w ere requested. Most were crop group updates. One request was to replace individual oilseed tolerances with an oilseed crop group 20 tolerance . This was accompanied by

a request to remove numerous individual commodity oilseed tolerances. These changes hav e been made to the proposed labels. Inaddition to the requested removals, the tolerance for cotton undelinted seed will be replaced by oilseed, group 20, and IR - 4 needs to make this request. The tolerance covering undelinted cotton seed is raised from 0.3 ppm to 0.45 ppm. This is acceptable as cottonseed is one of the three representative commodities for the oilseed group (cottonseed, rapeseed, sunflower), and the highest estimate from the three commod ities is adopted for the group. The changes are accept able, as detailed in Table 7 . **Table 7**  **Tolerance Sum ma**  **ry for Pyraclostrobin**  **.** Commodity Proposed/Existing Tolerance (ppm) Recommended/ Harmonized Tolerance (ppm) Comments; Correct Commodity

Definition 40CFR§180.582(a) It is recommended that a tolerance be established for residues of the fungicide pyraclostrobin, including its metabolites and degradates, as indicated below. . Compliance with the tolerance levels is to be determined by measuring only the sum of pyraclostrobin (carbamic acid, [2 - [[[1 - (4 - c hlorophenyl) - 1 H - pyrazol - 3 - yl]oxy]methyl]phenyl]methoxy- , methyl ester) and its desmethoxy metabolite (methyl N - [[[1 - (4 - chlorophenyl) - 1 Hpyrazol - 3 - yl]oxy]methyl]phenyl carbamate), calculated as the stoichiometric equivalent of pyraclostrobin Artichoke, globe 3.0 3.0 Endive, Belgium 3.0 4.0 OECD statistical calculation estimates 4.0 ppm. Persimmon 3.0 3.0 Vegetable, bulb, group 3 - 07 0.9 0.9 Group update Vegetable, bulb, group 3 0.9 Remove Group update Vegetable, fruiting, group 8 - 10 1.4 1.4 Group update Vegetable, fruiting, group 8 1.4 Remove Group update Fruit, citrus, group 10 - 10 2.0 2.0 Group update Fruit, citrus, group 10 2.0 Remove Group update Fruit, pome, group 11 - 10 1.5 1.5 Group update Fruit, pome, group 11 1.5 Remove Group update Oi lseed group 20 0.45 0.45 Group creation.Py

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Page **17** of **22 Table**  **7 Tolerance Sum**  **ma ry for**  **Pyraclostrobin .**  Commodity Proposed/Existing Tolerance (ppm) Recommended/ Harmonized Tolerance (ppm) Comments; Correct Commodity

Definition Cotton, undelinted seed 0.3 Remove To be replaced by oilseed, group 20 . IR - 4 needs to request this removal. Borage, seed 0.45 Remove To be replaced by oilseed, group 20. Castor oil plant, seed 0.45 Remove To b e replaced by oilseed, group 20. Chinese tallowtree, seed 0.45 Remove To be replaced by oilseed, group 20. Crambe, seed 0.45 Remove To be replaced by oilseed, group 20. Cuphea, seed 0.45 Remove To be replaced by oilseed, group 20. Echium, seed 0.45 Remove To be replaced by oilseed, group 20. Euphorbia, seed 0.45 Remove To be replaced by oilseed, group 20. Evening primrose, seed 0.45 Remove To be replaced by oilseed, group 20. Flax, seed 0.45 Remove To be replaced by oilseed, group 20. Gold of pleasure, seed 0.45 Remove To be replaced by oilseed, group 20. Hare's ear mustard, seed 0.45 Remove To be replaced by oilseed, group 20. Jojoba, seed 0.45 Remove To be replaced by oilseed, group 20. Lesquerella, seed 0.45 Remove To be replaced by oilseed, group 20. Lunaria, seed 0.45 Remove To be replaced by oilseed, group 20. Meadowfoam, seed 0.45 Remove To be replaced by oilseed, group 20. Milkweed, seed 0.45 Remove To be replaced by oilseed, group 20. Mustard, seed 0.45 Remove To be replaced by oilseed, group 20. Niger seed, seed 0.45 Remove To be replaced by oilseed, group 20. Oil radish, seed 0.45 Remove To be replaced by oilseed, group 20. Poppy , seed 0.45 Remove To be replaced by oilseed, group 20. Rapeseed , seed 0.45 Remove To be replaced by oilseed, group 20.Py

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Page **18** of **22 Table**  **7 Tolerance Sum**  **ma ry for**  **Pyraclostrobin .**  Commodity Proposed/Existing Tolerance (ppm) Recommended/ Harmonized Tolerance (ppm) Comments; Correct Commodity

Definition Rose hip, seed 0.45 Remove To be replaced by oilseed, group 20. Safflower, seed 0.45 Remove To be replaced by oilseed, group 20. Stokes aster, seed 0.45 Remove To be replaced by oilseed, grou p 20. Sunflower, seed 0.45 Remove To be replaced by oilseed, group 20. Sweet rocket, seed 0.45 Remove To be replaced by oilseed, group 20. Tallow wo od, seed 0.45 Remove To be replaced by oilseed, group 20. Tea oil plant, seed 0.45 Remove To be r eplaced by oilseed, group 20. Vernonia, seed 0.45 Remove To be replaced by oilseed, group 20. Caneberry subgroup 13 - 07A 4.0 4.0 Group update Bushberry subgroup 13 - 07B 4.0 4.0 Group update Small fruit, vine climbing subgroup (except fuzzy kiwi) 13 - 0 7F 2.0 2.0 Group update Low growing berry subgroup 13 - 07G except cranberry 1.2 1.2 Group update Berry, group 13 4.0 Remove Group update . Replaced with subgroups 13 - 07A and 13 - 07B Grape 2.0 Remove Group update. Replaced with subgroup 13 - 07F Straw berry 1.2 Remove Group update. Replaced with subgroup 13 - 07G 40CFR§180.582(b ) Section 18 emergency exemptions Endive, Be l gian 11.0 Remove Replaced with Section 3 tolerance for endive, Belgium **References** DP#s: 367409 Subject: Py

raclostrobin. Petition for New Uses and Tolerances on Alfalfa. Summary of Analy tical Chemistry

and Residue Data. From: W. Cutchin To: T. Kish/J. Bazuin Dated: 10/19/09 MRIDs: 47584401Py

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Page **19** of **22** DP#s: 281042, 286732, 287729, 288459, 290342, 290343, 290369, 292440, 293088,

293684, 295893, 29 8178 Subject: Py

raclostrobin. PP#3F06581, 2F06431, 2E6473, 3E6548, 3E6553, 3E6774, and 2F06139. Petitions for the establishment of permanent tolerances to allow uses on corn (field, sweet, and pop), hops, mint, pome fruits, edible - podded legume vegetable s, succulent peas, sunflower, Brassica leafy greens, soy

beans, succulent beans, broccoli, cabbage, lettuce (head and leaf), spinach, celery, turnip greens, and the import commodities mango and papaya. Application for amended Section 3 registration for citrus (reduced PHI). Petitioner’s response to data deficiencies identified in PP#0F06139 regarding storage stability data, dried shelled peas and beans (reduced PHI), and uses on dry and succulent peas. Summary of Analy tical Chemistry

and Residue Data. Fro m: L. Cheng To: C. Giles - Parker/J. Bazuin Dated: 7/26/04 MRIDs: 45596211, 45623406, 45623407, 45623408, 45623410, 45645801, 45645802,

45645803, 45645804, 45702901, 45765401, 45832001, 45858801, 45858802, 45903601, 45903602, 46033901 - 04, 46084401 - 04, 461091 01, 46109102 DP#s: 269668, 272771, 272789, 274095, 274192, 274471, 274957, 275843, and 278429 Subject: PP#0F06139. Py raclostrobin on Various Crops: Bananas (import), Barley, Berries, Bulb Vegetables, Citrus Fruits, Cucurbit Vegetables, Dried Shelled Pe a & Bean (except Soy

bean), Fruiting Vegetables, Grapes, Grass, Peanut, Pistachio, Root Vegetables (except Sugar Beet), Rye, Snap Beans, Stone Fruits, Strawberry , Sugar Beet, Tree Nuts, Tuberous and Corm Vegetables, and Wheat. Review of Analy tical Methods and Residue Data. From: L. Cheng To: C. Giles - Parker/J. Bazuin Dated: 11/28/01 MRIDs: 45118428 - 451184 - 37, 45118501 - 45118512, 45118514 - 45118537, 45118601 -

45118625, 45160501, 45272801, 45274901, 45321101, 45367501, 45399401, and 45429901 DP#: 278044 Subje ct: PP# 0F06139. PC Code 099100. Py raclostrobin. Outcome of the HED Metabolism Assessment Review Committee (MARC) Meeting Held on September 20, 2001. From: L. Cheng To: Y. Donovan Dated: 10/09/01 MRIDs: NonePy

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Page **20** of **22** DP#: 269850 Subject: PP# 0F06139. Py raclostrobin (BAS 500F) in or on Various Crops. Request for Tolerance Method Validation (TMV) Trial. From: L. Cheng To: F. D. Griffith, Jr. Dated: 11/8/00 MRIDs: 45118505, 45118504, 45118509, 45118510, 45118501, 45118503, 45118507,

45118514 DP#: 281042, 286732, 287729, 288459, 290342, 290343, 290369, 292440, 293088,

293684, 295893, 298178 Subject: Py

raclostrobin. PP#3F06581, 2F06431, 2E6473, 3E6548, 3E6553, 3E6774, and 2F06139. Petitions for the establishment of permanent tolerances to allow uses on corn (field , sweet, and pop), hops, mint, pome fruits, edible - podded legume vegetables, succulent peas, sunflower, Brassica leafy greens, soy

beans, succulent beans, broccoli, cabbage, lettuce (head and leaf), spinach, celery, turnip greens, and the import commodities mango and papaya. Application for amended Section 3 registration for citrus (reduced PHI). Petitioner’s response to data deficiencies identified in PP#0F06139 regarding storage stability data, dried shelled peas and beans (reduced PHI), and uses on dry and succulent peas. Summary of Analy tical Chemistry

and Residue Data. From: L. Cheng To: Cy

nthia Giles - Parker Dated: 7/26 /0 4 MRIDs: 45596211, 45623406, 45623407, 45623408, 45623410, 45645801, 45645802, 45645803,

45645804, 45702901, 45765401, 45832001, 458 58801, 45858802, 45903601, 45903602, 46033901 - 04, 46084401 - 04, 46109101, 46109102Py

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Page **21** of **22** 

### I nternational Residue Limits Pyraclostrobin ( 099100; 0 2 / 19 /2013 ) Summary of US and International Tolerances and Maximum Residue Limits Residue Definition : US Canada Mex ico 2 Codex 3 40 CFR §180.582. Plants: Tolerances are established for residues of the fungicide pyraclostrobin, including its metabolites and degradates. Compliance with the tolerance levels is to be determined by measuring on the sum of pyraclostrobin ( carbamic acid, [2 - [[[1 - (4 - chlorophenyl) - 1 H

- pyrazol - 3 - yl]oxy]methyl]phenyl]methoxy- , methyl ester) and its desmethoxy metabolite (methyl N - [[[1 - (4 - chlorophenyl) - 1 H

- pyrazol - 3 - yl]oxy]methyl]phenyl carbamate), calculated as the stoichiometric equivalent of p yraclostrobin methyl [2 - [[[1 - (4 - chlorophen yl) - 1 Hpyrazol - 3 - yl]oxy]met hyl]phenyl] methoxycar bamate, including the metabolite [2 - [[[1 - (4 - chlorophen yl) - 1 Hpyrazol - 3 - yl]oxy]met hyl]phenyl] carbamate - Py raclostrobin. Residue is NOT fat soluble.

Commodity 1 Tole rance (ppm) /Maximum Residue Limit ( ppm ) US Canada Mexico 2 Codex 3 Artichoke , globe 3.0 None 2. Belgium endive (witloof chicory) 4.0 None None Persimmon 3.0 None None 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.Py

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Page **22** of **22** 

### Appendix I: Determination of Tolerance for Pyraclostrobin in/on Sugarcane and Its Processed Fractions The Organization for Economic Cooperation and Development statistical procedure was used to calculate tolerances for artichoke, Belgium endive, and persimmon. The estimate s agree w ith the proposal s of IR - 4 for persimmon and artichoke. For Belgium endive, the IR - 4 tolerance estimate is 3.0 ppm from application before cold storage and again at pre - forcing. However, the single application at pre - forcing yielded higher residues, and these data were used to derive the tolerance estimate of 4.0 ppm. The average combined residue of py raclostrobin and BF 500 - 3 from each trial (n = 3)was used as the calculator entry value. **Compound Crop**  **Region / Country GAP**  **Total number of data (n) Percentage of censored data**  **Number of non-censored data Lowest residue**  **Highest residue Median residue**  **Mean Standard deviation (SD)**  **Correction factor for censoring (CF) Proposed MRL estimate**  **- Highest residue - Mean + 4 SD**  **- CF x 3 Mean Unrounded MRL**  **Rounded MRL**

**Residues (mg/kg) Residues (mg/kg)**  **Residues (mg/kg)** 0.638 0.920 0.112 1.101 0.170 1.228 0.787 1.367 0.457 3 0% **Pyraclostrobin Persimmon**  **Pyraclostrobin Artichoke**  **USA 3X0.19 ll ai/A, 0 d**  **USA 3X0.19 ll ai/A, 0 d** 

3 0.638 1.101 0.787 0.842 0.236

2.526 **3** High uncertainty of MRL estimate due to small dataset.

1.000

1.101 1.787 2.526 0.170 1.367 0.920 0.819 0.605 1.000

1.367 3.238 2.457 3.238 **4** High uncertainty of MRL estimate due to small dataset. 3 0.112 3 0%

1.228 0.457 0.599 0.571 1.000

1.228 2.885 1.797 2.885 **3** High uncertainty of MRL estimate due to small dataset. 3 **Pyraclostrobin Belgium Endive**  **USA 0.6 g ai/100 lbs root + 0.1 lb ai/ft2**  3 0%