Spir odiclofen Summary of Analytical Chemistry and Residue Data D363343

page 1 of 12 UNITED STATES ENVIRONMENTAL PROTECTION AGENCY

WA SHINGTON, D.C. 20460 OFFICE OF PREVENTION, PESTICIDES AND TOXIC SUBSTANCES MEMORANDUM Date: 2 3 - September - 200 9 Subject: Spirodiclofen in/on Avocado, Black Sapote, Canistel, Mamey Sapote, Mang o, Papaya, Sapodilla, and Star Apple. Summary of Analytical Chemistry and Residue Data. PC Code: 124871 DP Barcode: D 363343 Decision No.: 404221 Registration No. : 264 - 83 1 Petition No.: 8F7500 Regulatory Action: Section 3 Risk Assessment Type: not applicable Case No.: none T XR No.: not applicable CAS No.: 148477 - 71 - 8 MRID Nos: 47630101 40 CFR: 180.608 From: Tom Bloem, Chemist

Risk Assessment Branch I , Health Effects Division (RAB I/HED; 7509C) Through: George F. Kramer, Ph.D., Senior C hemist

HED/RABI(7509P) To: John Hebert/Rita Kumar (RM 07)

Registration Division (RD; 7505P) Bayer CropScience ( Research Triangle Par k , NC ) proposed the establishment of permanent tolerances for residues of spirodiclofen (3 - (2,4 - dichlorophenyl) - 2 - o xo - 1 - oxaspiro[4.5]dec - 3 - en 4 - yl2,2 - dimethylbutanoate; see attachment 1 for structure) in/on the following commodities: avocado ................................ ................................ ................................ ................................ 1.3 ppm black sapote ................................ ................................ ................................ .......................... 1.3 ppm canistel ................................ ................................ ................................ ................................ . 1.3 ppm mamey sapote ................................ ................................ ................................ ....................... 1.3 ppm mango ................................ ................................ ................................ ................................ ... 1.3 ppm papaya ................................ ................................ ................................ ................................ .. 1.3 ppm sapodilla ................................ ................................ ................................ ............................... 1.3 ppm star apple ................................ ................................ ................................ .............................. 1. 3 ppmSpir odiclofen Summary of Analytical Chemistry and Residue Data D363343

page 2 of 12 Executive Summary Background: Spirodiclofen is a tetronic acid with acaricidal action (group 23) . It acts by interfering with mite development and controls such pests as Panonychus spp., Phyllocoptruta spp., Brevipalpus spp., and Aculus and Tetranychus species. The petitioner stated that spirodiclofen is active by

contact to mite eggs, all ny mphal stages, and adult females (adult males are not effected). Spirodiclofen is currently registered for application to citrus fruit, grape, pome fruit, s tone fruit, tree nuts, and hops with tolerances for residues of spirodiclofen per se of 0.10 - 30 ppm; milk and ruminant meat, meat by products, and fat tolerance for the combined resi dues of spirodiclofen and BAJ 2510 are also established (0.02 - 0.1 ppm). Proposed Application Scenarios: The petitioner provided proposed use directions for application of Envidor® 2 SC Miticide (suspension - concentrate; 2 lbs ai/gallon ; EPA Reg. No. 264 - 831 ) to avocado, black sapote, canistel, mamey sapote, mango, papaya, sap odilla, and star apple (see Table 1 for summary ). Application through irrigation equipment and in enclosed structures is prohibited. Although the label does not indicate that adjuvants ( e . g. ; crop - oil concentrate, nonionic surfactant, methylated seed oi l) should be added to the spray solution, it does not prohibit the inclusion of adjuvants. Since the field trial data submitted in support of the proposed action did not include adjuvant s , HED requests a revised Section B prohibiting the addition of adjuv ants to the spray solution. Table 1 : Summary of Proposed Application Scenarios . Applic. Type Max. Single Applic.

Rate (lb ai/acre) Max. No. Applic.

per Season PHI 1

(days) Comments Avocado, Black Sapote, Canistel, Mam ey Sapote, Mango, Papaya, Sapodill a, and Star Apple

foliar spray 0. 28 - 0.31 1 2 ● Excluding avocado, applications may be made with ground equipment only (minimum spray volume of 50 gallons per acre (GPA)); for avocado, the label states that ground (minimum spray volume of 50 GPA) or aerial (minimum spray volume of 100 GPA) application equipment may be used . ● M aximum seasonal application rate - 0.31 lb ai/acre . ●L abel states the following pests are controlled - Avocado brown mite, Avocado red mite, B road mite, C armine spider mite, C itrus red mite, Flat mite (bl a ck and red), Mango spider mite, Papaya Leaf edgeroller mite, Persea mite, Sixspotted mite, Texas c itrus mite, and Twospotted spider mite . 1 PHI = preharvest interval . Nature of the Residue - Plants: Based on the results of previousl y submitted apple and grape processing studies and citrus, grape, and apple metabolism studies (D285249, T. Bloem, 18 - Apr 2005; D341847, T. Bloem, 25 - Oct - 2007; D359773, T. Bloem, 24 - Jun - 2009), HED concluded the following: (1) citrus fruit, pome fruit, sto ne fruit, and tree nut - the residue of concern for risk assessment and tolerance enforcement is spirodiclofen per se and (2) grape - the residue of concern for tolerance enforcement is spirodiclofen per se and residues of concern for risk assessment are s pirodiclofen and BAJ 2510. Since the grape processing study demonstrated degradation of spirodiclofen to BAJ 2510, HED is requesting that the petitioner submit an orange processing study

monitoring for residues of spirodiclofen, BAJ 2510, 3 - OH - enol, and 4 - OH - enol (apple processing study

did not demonstrate this degradation). Pending the submission of the orange processing data, human - health risk assessments should assume default processing factors for all processed commodities excluding the processed comm odities for apple and grape.Spir odiclofen Summary of Analytical Chemistry and Residue Data D363343

page 3 of 12 HED determined that these conclusions may be translated to the currently requested crops. The refore, the residues of concern in the currently requested crops is spirodiclofen per se . The following is a summary

of the curre ntly- available plant metabolism data. The apple, citrus, and grape metabolism studies indicate that the metabolism of spirodiclofen in fruit crops involves the following steps: cleavage of the ester linkage to form the free enol metabolite (BAJ 2510) ; hydroxylation of BAJ 2510 on the cyclohexyl rin g to form 3 - OH - enol and 4 - OH - enol metabolites; and cleavage of the enol ring structure to form 2,4 - dichloro mandelic acid - cyclohexylester , which undergoes hydroxylation/conjugation and further degradation to yield 2,4 - dichloro - mandelic acid (free and conjugated). The grape processing study indicates that residues of spirodiclofen degrade to BAJ 2510 during processing of grapes to juice, juice concentrate, jelly, and raisin (apple processing study did not demon strate this). The majority

of the residues in/on fruit were surface residues or were associated with the peel with nearly

all these being comprised of parent compound. Overall , spirodiclofen accounted for 34 - 99% of the total radioactive residues (TRR). Minor amounts of the following compounds were also identified: BAJ 2510 ( ≤2% TRR), 3 - OH - enol ( ≤3% TRR), 4 - OH - enol (<1% TRR), 2,4 - dichloro - mandelic acid - cyclohexylester compounds (free and conjugated; ≤9% TRR), and 2,4 - dichloro - mandelic acid (free and co njugate; ≤12% TRR). Magnitude of the Residue - Plants: Insupport of the proposed registration , five avocado field trials , conducted during 2007 and 2008 in the North American Free Trade Agreement (NAFTA) zones 3 (n=1) and 10 (n=4) , were submitted. Prov ided a revised Section B is submitted, the application scenario employed in the field trials supports the proposed application scenario and resulted in spirodiclofen per se residues in/on avocado fruit of <0.01 - 0.614 ppm (method and storage intervals were adequately validated) . The geographical representation of the field trial data conform to the data requirements specified in OPPTS 860.1500 for avocado. Based on the avocado field trial data and the tolerance calculator, HED concludes that an avocado tol erance of 1.0 ppm, for residues of spirodiclofen per se , is appropriate. Based o n guidance from the HED Chem istry

Science Advisory

Council (Chem SAC ) , HED will translate the avocado field trial data to black sapote, canistel, mamey sapote, mango, papaya, s apodilla, and star apple (Reviewer’s Guide and Summary

of HED ChemSAC Approvals for Amending Commodity Definitions [40CFR § 180.1(h)] and Crop Group/Subgroups [40 CFR § 180.41]; B. Schneider; 14 - Jun - 2002) . Therefore, the avocado residue data supports a to lerance of 1.0 ppm for residues of spirodiclofen per se in/on black sapote, canistel, mamey sapote, mango, papaya, sapodilla, and star apple. A revised Section F is requested. Analytical Enforcement Method: HED determined that the Bayer analy tical method 109351 was appropriate for enforcement of the hop, c itrus, grape, pome fruit, stone fruit, and tree nut tolerances and forwarded this method to Food and Drug Administration (FDA) for inclusion in the Pesticide Analy

tical Manual (PAM; D368434, T. Bloem, 23 - Sep - 2009). Based on the similarities of the data collection method and the tolerance enforcement method and since the tolerance enforcement method h as been validated on a fruit crop, HED concludes that the current enforcement method is appropriate for enforcement of the tolerances recommended as part of this petition.Spir odiclofen Summary of Analytical Chemistry and Residue Data D363343

page 4 of 12 FDA Multiresidue Methods : Spirodiclofen and BAJ 2510 were screened through the FDA Multiresidue Methods (MRM) protocols. The petitioner indicated that since both spirodiclofen and BAJ 2 510 are not N - methylcarbamates, naturally fluorescent, acids, phenols, or substituted ureas, Protocols A, B, and G were not performed. Therefore, testing was only performed for protocols C, D, E, and F. Protocol C modules DG1 and DG10 gave acceptable res ults for BAJ 2510 and spirodiclofen, respectively

(both are gas chromatograph/electron - capture detection (GC/ECD) systems). Using fortified orange samples, acceptable recoveries of spirodiclofen were attained through Protocols D (80 - 103%) and E (54 - 77%). Using fortified ground beef samples, unacceptable recoveries of spirodiclofen were attained through protocol F (16 - 30%). BAJ 2510 was not recovered through the florisil clean - up column, and therefore, gave unacceptable recoveries for Protocol D (fortifie d orange samples) and F (fortified ground beef samples). Since BAJ 2510 was not recovered through Protocol D, Protocol E was not tested. These data have been forwarded to FDA (D308565, T. Bloem, 29 - Sep - 2004). Nature /Magnitude of the Residue - Livestock: Based on the revised Table 1 feeds tuffs (OPPTS 860.1000), none of the proposed crops have feed commodities; therefore a discussion concerning the nature/magnitude of the residue in livestock is unnecessary . Nature/Magnitude of the Residue - Rotational Crops: Since all of the requested crops are perennials, a discussion concerning the nature/magnitude of the residue in rotational crops is unnecessary . Recommendations: Provided the petitioner submits revised Section s B and F , HED concludes that the residu e chemistry database supports an un conditional registration and establishment of the following permanent tolerances for residues of spirodiclofen per se : Avocado - 1.0 ppm , Black s apote - 1.0 ppm , Canistel - 1.0 ppm , Mamey s apote - 1.0 ppm , Mango - 1.0 ppm , Papaya - 1.0 ppm , Sapodilla - 1.0 ppm , and Star a pple - 1.0 ppm. Summary of Residue Chemistry Deficiencies:

 Revised Section B  Revised Section FSpir odiclofen Summary of Analytical Chemistry and Residue Data D363343

page 5 of 12 Detailed Considerations Background Spirodiclofen is a tetronic acid with acaricidal action (group 23) . It acts by interfering with mite development, and controls such pests as Panonychus spp., Phyllocoptruta spp., Brevipalpus spp., and Aculus and Tetranychus species. The petitioner stated that spirodiclofen is active by contact to mite eggs, all ny

mphal stages, and adult females (adult males are not effected). Tables 2 and 3 are summaries of spirodiclofen nomenclature and physical chemical properties, respectively . Table 2: Nom enclature. Spirodiclofen O O Cl Cl

O O C H 3 C H 3 C H 3

Common name Spirodiclofen Company exp erimental name BAJ2740 IUPAC name 3 - (2,4 - dichlorophenyl) - 2 - oxo - 1 - oxaspiro[4,5]dec - 3 - en - 4 - yl 2,2 - dimethylbutyrate CAS name 3 - (2,4 - dichlorophenyl) - 2 - oxo - 1 - oxaspiro[4,5]dec - 3 - en - 4 - yl 2,2 - dimethylbutanoate CAS registry number 148477 - 71 - 8 End - use product (E P) 2 lb/gal FlC (ENVIDOR® 2 SC Miticide; EPA Reg. No. 264 - 831) Table 3: P hysicochemical Properties of Spirodiclofen . Melting point 94.8oC

D315459, S . Mathur , 20 - Apr - 2005 pH 4.2 Density (20oC) 1.29 g/cm3 Water solubility (20oC at pH 4) 5 0μg/L

Solvent solubility (g/L at 20°C) n - heptane xylene dichloromethane 2 - propanol 1 - octanol polyethylene glycol acetone ethyl acetate acetonitrile dimethylsulfoxide 20

>250 >250 47 44 24 >250 >250 >250 75 Vapor pressure (20oC) 3 x 10 - 7 Pa Disso ciation constant, pKa Not determinable due to the instability in aqueous solutions at >pH 4 Log(KOW) at pH 4 and 20oC 5.83 UV/visible absorption spectrum λmax = 201 nm: Not expected to absorb UV at λ >350 nmSpir odiclofen Summary of Analytical Chemistry and Residue Data D363343

page 6 of 12 860.1200 Directions for Use The petit ioner provided proposed use directions for application of Envidor® 2 SC Miticide (2 lbs ai/gallon; EPA Reg. No. 264 - 831) to avocado, black sapote, canistel, mamey sapote, mango, papaya, sapodilla, and star apple. (see Table 1 for summary ). Application through irrigation equipment and in enclosed structures is prohibited. Although the label does not indicate that adjuvants (crop oil concentrate, nonionicsurfactant, methy lated seed oil) should be added to the spray solution, it does not prohibit the inclusi on of adjuvants. Since the field trial data submitted in support of the proposed action did not include adjuvants, HED requests a revised Section B prohibiting the addition of adjuvants to the spray solution. 860.1300 Nature of the Residue - Plants Ba sed on the results of previously submitted apple and grape processing studies and citrus, grape, and apple metabolism studies (D285249, T. Bloem, 18 - Apr - 2005; D341847, T. Bloem, 25 - Oct 2007; D359773, T. Bloem, 24 - Jun - 2009), HED concluded the following: (1 ) citrus fruit, pome fruit, stone fruit, and tree nut - the residue of concern for risk assessment and tolerance enforcement is spirodiclofen per se and (2) grape - the residue of concern for tolerance enforcement is spirodiclofen per se and residues of co ncern for risk assessment are spirodiclofen and BAJ 2510. Since the grape processing study demonstrated degradation of spirodiclofen to BAJ 2510, HED is requesting that the petitioner submit an orange processing study monitoring for residues of spirodiclo fen, BAJ 2510, 3 - OH - enol, and 4 - OH - enol (apple processing study did not demonstrate this degradation). Pending the submission of the orange processing data, human - health risk assessments should assume default processing factors for all processed commoditi es excluding the processed commodities for apple and grape. HED has determined that these conclusions may be translated to the currently requested crops. The refore, the residues of concern in the currently requested crops is spirodiclofen per se . The following is a summary

of the currently- available plant metabolism data. The apple, citrus, and grape metabolism studies indicate that the metabolism of spirodiclofen in fruit crops involves the following steps: cleavage of the ester linkage to form th e free enol metabolite (BAJ 2510) ; hydroxylation of BAJ 2510 on the cyclohexyl rin g to form 3 - OH - enol and 4 - OH - enol metabolites; and cleavage of the enol ring structure to form 2,4 - dichloro mandelic acid - cyclohexylester , which undergoes hydroxylation/conju gation and further degradation to yi eld 2,4 - dichloro - mandelic acid (free and conjugated). The grape processing study indicates that residues of spirodiclofen degrade to BAJ 2510 during processing of grapes to juice, juice concentrate, jelly, and raisin (a pple processing study

did not demonstrate this) . The majority

of the residues in/on fruit were surface residues or were associated with the peel with nearly

all th ese being comprised of parent compound. Overall , spirodiclofen accounted for 34 - 99% TRR. Minor amounts of the following compounds were also identified: BAJ 2510 ( ≤2% TRR), 3 - OH - enol ( ≤3% TRR), 4 - OH - enol (<1% TRR), 2,4 - dichloro - mandelic acid cyclohexylester compounds (free and conjugated; ≤9% TRR), and 2,4 - dichloro - mandelic acid (free and con

jugate; ≤12% TRR).Spir odiclofen Summary of Analytical Chemistry and Residue Data D363343

page 7 of 12 860.1300 Nature of the Residue - Livestock Based on the revised Table 1 feedstuffs (OPPTS 860.1000), none of the proposed crops have feed commodities; therefore a discussion concerning the nature of the residue in livestock is unneces sary . 860.1340 Residue Analytical Methods Data Collection: The avocado field trial samples were analy zed for residues of spirodiclfen per se using a liquid chromatograph/mass spectrometer/mass spectrometer ( LC /MS/MS ) method . Briefly , pitted homogeniz ed samples were extracted by blending with acetonitrile (ACN) :water (2:1; v:v) containing a small amount of aqueous 20% cysteine hydrochloride. I sotopically labeled internal standard were added and the extracts were centrifuged, filtered through a nylon s yringe filter, and analy

zed via L C/MS/MS. Acceptable concurrent recoveries were attained for samples fortified with spirodiclofen at 0.01 - 1.0 ppm (93 - 116%). Based on these acceptable recoveries and since the extraction solvent employed in the data collec tion method is identical to that employed in the tolerance enforcement method (see below), HED concludes that method is acceptable for data collection purposes. Based on the lower limit of method validation ( LLM V ) , the limit of quantitation ( LOQ ) is 0.01 ppm. The statistically determined limit of detection ( LOD ) is 0.0017 ppm (standard deviation at 0.01 ppm multiplied by the one - tailed 99% t - stat). Tolerance Enforcement: HED forwarded Bayer analy tical method 1 09351 t o FDA for inclusion in the PAM ( D36 8434, T. Bloem, 23 - Sep - 2009 ). Briefly , the fruit samples were extracted with ACN:water (2:1; v:v) containing a small amount of aqueous 20% cysteine hydrochloride , filtered, and an aliquot of the filtrate was acidified with HCl . The extracted residues were subjected to clean up on an ENVI - carb cartridge preconditioned with dichloromethane ( DCM ) , methanol , and water with residues eluted out with DCM under vacuum. The eluted residues were concentrated to dry

ness and reconstituted in ACN and water for analys is by L C/MS/MS. The L OQ was reported to be 0.01 ppm (LOD ranged from 0.001 - 0.006 ppm). Based on the similarities of the data collection method and the tolerance enforcement method and since the tolerance enforcement method h as been validated on a fruit c rop, HED concludes that the current enforcement method is appropriate for enforcement of the tolerances recommended as part of the this petition. 860.1360 Multiresidue Methods Spirodiclofen and BAJ 2510 were screened through the FDA MRM protocols. The petitioner indicated that since both spirodiclofen and BAJ 2510 are not N - methylcarbamates, naturally fluorescent, acids, phenols, or substituted ureas, Protocols A, B, and G were not performed. Therefore, testing was only performed for protocols C, D, E , and F. Protocol C modules DG1 and DG10 gave acceptable results for BAJ 2510 and spirodiclofen, respectively

(both are GC/ECD systems). Using fortified orange samples, acceptable recoveries of spirodiclofen were attained through Protocols D (80 - 103%) an d E (54 - 77%). Using fortified ground beef samples, unacceptable recoveries of spirodiclofen were attained through protocol F (16 - 30%). BAJ 2510 was not recovered through the florisil clean - up column, and therefore, gave unacceptable recoveries for Protoc ol D (fortified orange samples) and F (fortified ground beef samples). Since BAJ 2510 was not recovered through Protocol D, Protocol E was not tested. These data have been forwarded to FDA (D308565, T. Bloem, 29 - Sep - 2004).Spir odiclofen Summary of Analytical Chemistry and Residue Data D363343

page 8 of 12 860.1380 Storage Stability The avocado fruit sample s from the field trials were stored frozen for up to 282 days prior to analysis. The petitioner previous ly submitted storage stability data which indicated that residues of spirodiclofen per se are stable when stored frozen for the fo llowing crop/intervals (D285249, T. Bloem, 18 - Apr - 2005): 391 days (grape), 231 days (raisin), 226 days (grape juice concentrate), 231 days (apple juice concentrate), 231 days (dried apple), 391 days (peaches), 306 days (prunes), 410 days (almond nutmeat), and 305 days (almond hulls). The almond hull data indicated a 26% reduction in residues for samples stored 410 days. These data support the storage intervals and conditions for the avocado fruit samples collected as part of the current study . 860.1480 Meat, Milk, Poultry, and Eggs Based on the revised Table 1 feedstuffs (OPPTS 860.1000), none of the proposed crops have feed commodities; therefore a discussion concerning the magnitude of the residue in livestock is unnecessary . 860.1500 Crop Field Tr ials 47630101.der.doc Insupport of the proposed registration , five avocado field trials , conducted during 2007 and 2008 in NAFTA zones 3 (n=1) and 10 (n=4) , were submitted (47630101.der.doc; see below) . Provided a revised Section B is submitted, the app lication scenario employed in the field trials supports the proposed application scenario and resulted in spirodiclofen per se residues in/on avocado fruit of <0.01 - 0.614 ppm (method and storage intervals were adequately vlaidated) . The geographical repre sentation of the field trial data conform to the data requirements specified in OPPTS 860.1500 for avocado. Based on the avocado field trial data and the tolerance calculator, HED concludes that an avocado tolerance of 1.0 ppm , for residues of spirodiclof en per se , is appropriate (see attachment 3 ). Based o n guidance from the HED ChemSAC, HED will translate the avocado field trial data to black sapote, canistel, mamey sapote, mango, papaya, sapodilla, and star apple (Reviewer’s Guide and Summary .....; B. S chneider; 14 - Jun - 2002). Therefore, the avocado residue data supports a tolerance of 1.0 ppm for residues of spirodiclofen per se in/on black sapote, canistel, mamey sapote, mango, papaya, sapodilla, and star apple. A revised Section F is requested. Av ocado (4 7630101 .der.wpd): Bayer CropScience submitted residue data for five avocado trials conducted during 2007 and 2008 in the North American Free Trade Agreement (NAFTA ) zones 3 (n=1) and 10 (n=4). Each trial consisted of one untreated plot and two treated plots. The treated plots received a single foliar broadcast application of a 2 lb ai/gallon spirodiclofen SC formulation at 0.309 - 0.328 lb ai/acre. The treated plots differed in that one employed a dilute spray volume (218 - 363 GPA) and the other employed and a concentrate spray volume (46 - 70 GPA). Applications were made using ground equipment and did not include the use of any spray adjuvants. Duplicate control and treated avocado fruit samples were collected from each trial 2 days after treatment . Additional samples were collected at two of the field trials 0, 5, 7, and 10 days after application. The LC/MS/MS method used to determine residues of spirodiclofen per se in avocado was adequately

validated in conjunction with the analysis of field trial samples. Based on the LLM V , the L OQ is 0.01 ppm (residues in controls <L OQ) . The statistically determined limit of detectionSpir odiclofen Summary of Analytical Chemistry and Residue Data D363343

page 9 of 12 (LOD) is 0.0017 ppm (standard deviation at 0.01 ppm multiplied by the one - tailed 99% t - stat). The storage intervlas were a lso validated. Following a single foliar application of spirodiclofen (SC) at 0.309 - 0.328 lb ai/acre, residues of spirodiclofen per se were <0.01 - 0.614 ppm (dilute/concrete spray volumes ; see Table 4 ). A paired t - test (two - tailed) analysis of the side - by- side field trials indicates that spirodiclofen residues were not influenced by spray volume (dilute (218 - 363 GPA) - vs - concentrate (46 - 70 GPA)). The residue decline data indicate that residue of spirodiclofen per se declined as the PHI increased from 0 to 10 days. Table 4 : Sum ma ry of Avocado Residue Data. Commodity Total App. Rate

(lb ai/A); Spray Vol. PHI (days) Residue Levels (ppm) 1

n Min. Max. HAFT 2 Median Mean Std. Dev. Avocado 0.309 - 0.328; conc. 2 10 <0.01 0.614 0.474 0.063 0.134 0.195

0.312 - 0.322; dilute 2 10 0.015 0.204 0.192 0.085 0.094 0.063 0.309 - 0.328; both conc. and dilute 2 20 <0.01 0.614 0.474 0.070 0.110 0.143 1 Based on the LLMV, the LOQ = 0.01 ppm; LOD = 0.0017 ppm. 2 HAFT = highest average field trial. 860.1520 Proce ssed Food and Feed Based on Table 1 of OPPTS 860.1000, there are not processed commodities associated with the proposed crops. 860.1850/860.1900 Confined and Field Accumulation in Rotational Crops Since all of the requested crops are perennials, a dis cussion concerning the nature/magnitude of the residue in rotational crops is unnecessary . 860.1550 Proposed/Recommended Tolerances Table 5 is a summary

of the proposed and recommended tolerances for residues of spirodiclofen per se . A revised Sectio n F should be submitted. There are no Codex , Canadian, or Mexican maximum residue limits (MRL s) in/on the requested crops. The refore, harmonization is not an issue for this registration. Table 5 : Tolerance Sum ma ry . Commodity Proposed Tolerance (ppm) HED - Recommended Tolerance (ppm) Comments Avocado 1.3 1.0 A revised Section F , specifying the correct tolerance value , is requested . Black Sapote 1.3 1.0 Canistel 1.3 1.0 Mamey Sapote 1.3 1.0 Mango 1.3 1.0 Papaya 1.3 1.0 Sapodilla 1.3 1.0 Star Apple 1.3 1.0 Attachment 1: Chemical Structures Attachment 2: Codex Attachment 3: Tolerance Calculation RDI : RAB1 Chemists ( 29 - July- 2009) T. Bloem:S10945:Potomac Yard 1:703 - 605 - 0217:7509P:RAB1Spir odiclofen Summary of Analytical Chemistry and Residue Data D363343

page 10 of 12 Attachment 1: Chemical Structures

Chemical Nam e Structure Spirodiclofen; BAJ2740 3 - (2,4 - dichlorophenyl) - 2 - oxo - 1 - oxaspiro[4,5]dec - 3 - en - 4 - yl 2,2 - dimethylbutanoate O O Cl Cl

O O C H 3 C H 3 C H 3

BAJ 2510 3 - (2,4 - dichlorophenyl) - 4 - hydroxy - 1 - oxaspiro[4.5]dec - 3 - en - 2 - one O Cl Cl

O O H

3 - OH - enol 3 - OH - enol spirodiclofen O Cl Cl

O O H O H

4 - OH - enol 4 - OH - enol spirodiclofen O Cl Cl

O O H

O HSpir odiclofen Summary of Analytical Chemistry and Residue Data D363343

page 11 of 12 Attachment 2: International residue L imit Status 

## INTERNATIONAL RESIDUE LIMIT STATUS Chemical Nam e : 3 - (2,4 - dichlorophenyl) - 2 - oxo - 1 - oxaspir o[4,5]dec - 3 - en - 4 - yl 2,2 - dimethylbutanoate Com mo n Nam e: spirodiclofen Proposed tolerance Reevaluated tolerance X Other - HED recommended tolerances Date: 23 - Jul - 2009 Codex Status (Maximum Residue Limits) U. S. Tolerances √ No Codex proposal step 6 or above No Codex proposal step 6 or above for the crops requested Petition Number: 8F7500 DP Number: 36 3343 Other Identifier: Residue definition: N/A Reviewer/Branch: Tom Bloem/RAB1 Residue definition: spirodicl0fen Crop (s) MRL (mg/kg) Crop(s) Tole rance (ppm) Avocado 1.0 Black Sapote 1.0 Canistel 1.0 Mamey Sapote 1.0 Mango 1.0 Papaya 1.0 Sapodilla 1.0 Star Apple 1.0 Limits for Canada Limits for Mexico No Limits √ No Limits for the crops requested √ No Limits (no information after 2004) No Limits for the crops requested Residue definition: 3 - (2,4 - dichlorophenyl) - 2 - oxo - 1 - oxaspiro[4.5]dec - 3 - en - 4 - yl 2,2 - dimethylbutanoate, including the metabolite 1 - oxaspiro[4 .5]dec - 3 - en - 2 - one, 3 - (2,4 - dichlorophenyl) - 4 - hydroxy - (9CI) Residue definition: N/A Crop(s) MRL (mg/kg) Crop(s) MRL (mg/kg)

Notes/Special Instructions: S.Funk , 07/27/2009.Spir odiclofen Summary of Analytical Chemistry and Residue Data D363343

page 12 of 12 Attachment 3: Tolerance Calculation

Regulator: EPA Chemical: spirodiclofen Crop: avocado PHI: 2 days App. Rate: 1 x 0.309-0.328 lb ai/acre Submitter: IR-4

n: 20 min: 0.01 max: 0.61 median: 0.07 average: 0.11 95th Percentile 99th Percentile 99.9th Percentile 0.35 0.45 0.60 (0.50) (0.60) (--) 0.45 1.0 2.5 (1.1) (3.5) (--) 0.30 0.60 0.40 0.9659 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 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 = 1.2126x - 2.7862 R 2 = 0.9659

PercentilesConcentrations EPA spirodiclofen avocado 2 days 1 x 0.309-0.328 lb ai/acre IR-4