Spirodiclofen Summary of Analytical Chemistry and Residue Data D3 8 7 339

P age 1 of 13 

### UNITED STATES ENVIRONMENTAL PROTECTION AGENCY

WA SHINGTON, D.C. 20460 OFFICE OF C HEMI CAL SAFETY AND POLLU TION PREVENTION 

### MEMORANDUM Date: 15 - October - 201 1 Subject: **Spirodiclofen** in/on Sugar Apple, Cherimoya, Atemoya, Custard Apple, I lama,

Soursop, Biriba, Lychee, Longan, Spanish Lime, Rambutan, Pulasan, Guava, Feijoa, Jaboticaba, Wax Jambu, Starfruit, Passionfruit, Persimmon, and Acerola . Summary of Analy tical Chemistry

and Residue Data. **PC Code:** 124871 **DP Barcode:** D 3 87339 **Decision No.:** 4 43557 **Registration No. :**  264 - 83 1 **Petition No.:** 0E7820 **Regulatory Action:** Section 3 **Risk Assessment Type:** not applicable **Case No.:** 7443 **T XR No.:**  not applicable **CAS No.:** 148477 - 71 - 8 **MRID Nos:** 48332901, 48332902, and 48332903 **40 CFR:** 180.608 

### From: Tom Bloem, Chemist

Risk Assessment Branch 1 , Health Effects Division (RAB 1 /HED; 7509C) Through: George F. Kramer, Ph.D., Senior Chemist

HED/RAB 1 (7509P) To: Barbara Madden/Laura Nolle n (RM 0 5 )

Registration Division (RD; 7505P) Interregional Research Project Number 4 (IR - 4; Princeton, NJ ) proposed a Section 3 registration for application of spirodiclofen (3 - (2,4 - dichlorophenyl) - 2 - oxo - 1 - oxaspiro[4.5]dec - 3 - en - 4 - yl2,2 - dimethylbutanoate; see attachment 1 for structure) to sugar apple, cherimoya, atemoya, custard apple, ilama, soursop, biriba, lychee, longan, Spanish lime, rambutan, pulasan, guava, feijoa, jaboticaba, wax jambu, starfruit, passionfruit, persimmon , and acerola . In conjunction with the request, the petitioner proposed the establishment of the following spirodiclofen per se tolerances: sugar apple - 0.45 ppm; cherimoya - 0.45 ppm; atemoya - 0.45 ppm, custard apple - 0.45 ppm; ilama - 0.45 ppm; soursop - 0.45 ppm; biriba - 0.45 ppm; lychee - 3.5 ppm; longan - 3.5 ppm; Spanish lime - 3.5 ppm ; rambutan - 3. 5 ppm; pulasan - 3. 5 ppm; guava - 0.45 ppm; feijoa - 0.45 ppm; jaboticaba - 0.45 ppm; wax jambu - 0.45 ppm; starfruit - 0.45 ppm; passionfruit - 0.45 ppm; persimmon - 0.45 ppm; and acerola - 0.45 ppm.Spirodiclofen Summary of Analytical Chemistry and Residue Data D3 8 7 339

P age 2 of 13 

### Executive Summary **Background:** Spirod iclofen 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 s pirodiclofen 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, stone fruit, tree nuts, bushberry subgroup 13 - 0 7B, avocado, black sapote, canistel, mamey sapote, mango, papaya, sapodilla, star apple, and hops with tolerances for residues of spirodiclofen per se of 0.10 - 30 ppm; milk , milk fat, and ruminant meat, meat by product, and fat tolerance for the combined res i dues of spirodiclofen and BAJ 2510 are also established (0.02 - 0.1 ppm). **Proposed Application Scenarios:** The peti tioner proposed use directions for application of Envidor® 2 SC Miticide (suspension - concentrate; 2 lbs ai/gallon; EPA Reg. No. 264 - 831) t o sugar apple, cherimoya, custard apple, ilama, soursop, biriba, lychee, longan, Spanish lime, rambutan, pulasan, guava, feijoa, jaboticaba, wax jambu, starfruit, passionfruit, persimmon, atemoya, and acerola. Application through irrigation equipment and in enclosed structures is prohibited. See Table 4 for a summary of the proposed application scenario. HED request s a revised Section B which prohibits the addition of an adjuvant to the spray solution for the proposed cro ps. **Nature /Magnitude**  **of the Re sidue**  **- 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/magnitude of the residue in livestock is unnecessary . **Nature/Magnitude of the Re sidue**  **- Rotational Crops:**  Since all of the requested crops are perennials, a discussion concerning the nature/magnitude of the residue in rotational crops is unnecessary . **Nature of the Residue -**  **P rimary Crops**  **:** Based on the results of the citrus, grap e, and apple metabolism studies ( Risk Assessment Document: D285047, M Clock - Rust et al. , 22 - Jun - 2005 ); the apple, grape, and orange processing studies (D341847, T. Bloem, 22 - Jun - 2005; D359773, T. Bloem, 24 - Jun - 2009; D390192, T. Bloem, 20 - Jun - 2011); and pr evious conclusions relating to the residues of concern in hops (D346710, M. Sahafeyan, 3 - Jan - 2008); HED concludes that the residues of concern in the currently- registered /proposed crops are as follows (see Table 5 for a summary ) : pome fruit , tree nut , and hops - the residue of concern for risk assessment and tolerance enforcement is spirodiclofen per se and grape, citrus fruit, stone fruit, berry (crop group (CG) 13), and tropical fruit - the residue of concern for tolerance enforcement is spirodiclofen pe r se and residues of concern for risk assessment are spirodiclofen and BAJ 2510. HED notes that following: **(1)** BAJ 2510 is included as a residue of concern in grape, citrus fruit, stone fruit, berry (CG 13), and tropical fruit due to the demonstrated (grape and citrus fruit) degradation of parent to BAJ 2510 during processing or due to the lack of data eliminating this possibility (stone fruit , berry

CG 13, and tropical fruit); **(2)** BAJ 2510 is only a residue of concern in the processed commodities of grap e, citrus fruit, stone fruit, berry (CG 13), and tropical fruit ; and **(3)** if processing data for the combined residues of spirodiclofen and BAJ 2510 are not available, then the dietary

analysis should incorporate default processing factors. **Ba sed on the re**  **sults of the grape and orange processing studies, HED request**  **s that all future processing studies**  **monitor for residues of spirodiclofen, BAJ 2510, 3 -**  **OH -**  **enol, and 4 -**  **OH -**  **enol.**Spirodiclofen Summary of Analytical Chemistry and Residue Data D3 8 7 339

P age 3 of 13 

### Magnitude of the Residue **- P**  **rimary Crops :**  Insupport of the proposed registratio n, the petitioner submitted field trial studies conducted with lychee (n=3; North American Free Trade Agreement (NAFTA) Growing Zone 13), sugar apple (n=3; NAFTA Growing Zone 13), and guava (n=3; NAFTA Growing Zone 13). Provided the label is revised to prohibit the addition of adjuvants to the spray

solution, the application scenario employed in the field trials supports the proposed application scenario . Residues of spirodiclofen per se were as follows (method and storage intervals are validated) : lyche e - 0.579 - 1.54 ppm; sugar apple - 0.051 - 0.194 ppm; and guava - 0.033 - 0.247 ppm. The number and locations of the lychee, sugar apple, and guava field trials are adequate to support registration for these crops. Based on Table 1 of OPPTS 860.1000, processi ng studies are not required for the proposed crops. HED has previously

approved the following data translations (Reviewer = s Guide and Summary of HED ChemSAC Approvals for Amending Commodity Definitions [40 CFR ' 180.1(h)] and Crop Group/Subgroups [40 CFR ' 180.41], B. Schneider, 14 - June - 2002; see Chemistry Science Advisory Committee (ChemSAC) Database): lychee to longan, Spanish lime, rambutan, and pulasan; sugar apple to atemoya, custard apple, cherimoya, ilama, soursop, and birida; and guava to feijoa, jaboticaba, wax jambu, starfruit, passionfruit, and acerola. In addition, the ChemSAC previously

approved the translation of spirodiclofen guava residue data to persimmon provided the application scenario for each was identical (ChemSAC minutes of the 17 -Nov - 2010 meeting). Therefore, b ased on the available residue data and the Organization for Economic Cooperation and Development ( OECD ) tolerance calculator, HED concludes that the following tolerances for residues of spirodiclofen per se are appropriate ( a revised Section F is requested): lychee - 4.0 ppm; longan - 4.0 ppm; Spanish lime - 4.0 ppm; rambutan - 4.0 ppm; pulasan - 4.0 ppm; sugar apple - 0.40 ppm; atemoya - 0.40 ppm; custard apple - 0.40 ppm; cherimoya - 0.40 ppm; ilama - 0.40 ppm; soursop - 0 .40 ppm; birida - 0.40 ppm; guava - 0.50 ppm; feijoa - 0.50 ppm; jaboticaba - 0.50 ppm; wax jambu - 0.50 ppm; starfruit - 0.50 ppm; passionfruit - 0.50 ppm; acerola - 0.50 ppm; and persimmon - 0.50 ppm. **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 Manua l (PAM; D368434, T. Bloem, 23 - Sep - 2009). Based on the similarities of the tolerance enforcement and the adequately validated data collection methods , HED concludes that the current enforcement method is appropriate for enforcement of the tolerances recomm ended as part of the current petition. **FDA Multiresidue Methods**  **:** Spirodiclofen and BAJ 2510 were screened through the FDA MRM protocols. Since both spirodiclofen and BAJ 2510 are not N - methylcarbamates, naturally fluorescent, acids, phenols, or substi tuted ureas, testing through protocols A, B, and G is unnecessary . Protocol C modules DG1 and DG10 gave acceptable results for BAJ 2510 and spirodiclofen, respectively (both are gas chromatography /electron - capture detector ( GC/ECD ) sy stems). Using fortif

ied 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 n ot recovered through the florisil clean - up column, and therefore, gave unacceptable recoveries for Protocol 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).Spirodiclofen Summary of Analytical Chemistry and Residue Data D3 8 7 339

P age 4 of 13 

### Recommendations: Provided revised Section s B and F are submitted, HED concludes that the residue chemistry

database supports an un conditional registration for application of spirodiclofen to the proposed crops and establishment of the following permanent tolerance for residues of only spirodiclofen (180.608(a)(1)): lychee - 4.0 ppm; longan - 4.0 ppm; Spanish lime - 4.0 ppm; rambutan - 4.0 ppm; pulasan - 4.0 ppm; sugar apple - 0.40 ppm; atemoya - 0.40 ppm; custard apple - 0.40 ppm; cherimoya - 0.40 ppm; ilama - 0.40 ppm; soursop - 0.40 ppm; birida - 0.40 ppm; guava - 0.50 ppm; feijoa - 0.50 ppm; jaboticaba - 0.50 ppm; wax jambu - 0.50 ppm; starfruit - 0.50 ppm; passionfruit - 0.50 pp m; acerola - 0.50 ppm; and persimmon - 0.50 ppm . Inaccordance with the most recent guidance concerning tolerance expressions, HED recommends that the tolerance expression for 180.608(a)(1) and 180.6(a)(2) be changed as indicated below. HED notes that th is alteration in the tolerance expression does not necessitate a change in the currently

established or recommended tolerance levels. A revised Section F specifying the new tolerance expression , the currently established commodity

/tolerance levels, and th e HED - recommended tolerance s should be submitted. 180.608(a)(1): Tolerances are established for residues of spirodiclofen , including its metabolites and degradates, in or on the commodities listed below. Compliance with the following tolerance levels is to be determined by

measuring only spirodiclofen (3 - (2,4 - dichlorophenyl) - 2 - oxo - 1 - oxaspiro[4.5]dec - 3 - en - 4 - yl2,2 - dimethylbutanoate ) . 180.608(a) ( 2): Tolerances are established for residues of spirodiclofen, including its metabolites and degradates, in o r on the commodities listed below. Compliance with the following tolerance levels is to be determined by

measuring only spirodiclofen (3 - (2,4 - dichlorophenyl) - 2 - oxo - 1 - oxaspiro[4.5]dec - 3 - en - 4 - yl2,2 - dimethylbutanoate ) and its metabolite 3 - (2,4 - dichlorophenyl) - 4 - hydroxy- 1 - oxaspiro[4,5] dec - 3 - en - 2 - one . 

### Summary of Residue Chemistry Deficiencies:

 Revised Section B which prohibits the addition of an adjuvant to the spray solution for the proposed cro ps.  Revised Section F .Spirodiclofen Summary of Analytical Chemistry and Residue Data D3 8 7 339

P age 5 of 13 

### Detailed Considerations **Backgroun d**  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 1 and 2 are summaries of spirodiclofen nomenclature and physical chemical properties, respectively . **Table 1**  **: Nom**  **enclat ure.**  Spirodiclofen O O Cl Cl

O O C H 3 C H 3 C H 3

Common name Spirodiclofen Company experimental 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 - dimethylb utanoate CAS registry number 148477 - 71 - 8 End - use product (EP) 2 lb/gal FlC (ENVIDOR® 2 SC Miticide; EPA Reg. No. 264 - 831) **Table 2**  **: P**  **hysicochem ical Properties of**  **Spirodiclofen .**  Melting point 94.8oC

D315459, S . Mathur , 20 - Apr - 2005 pH 4.2 Density (2 0oC) 1.29 g/cm3 Water solubility (20oC at pH 4) 50μg/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 Diss ociation 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 nmSpirodiclofen Summary of Analytical Chemistry and Residue Data D3 8 7 339

P age 6 of 13 

### 860.1200 Directions for Use The peti tioner proposed use directions for application of Envidor® 2 SC Miticide (suspension concentrate; 2 lbs ai/gallon; EPA Reg. No. 264 - 831) to sugar apple, cherimoya, atemoya, custard apple, ilama, soursop, biriba, lychee, longan, Spanish lime, rambutan, pula san, guava, feijoa, jaboticaba, wax jambu, starfruit, passionfruit, persimmon, and acerola . Table 3 is a summary of the proposed formulation and target pests and Table 4 is a summary of the proposed application scenario. HED request s a revised Section B which prohibits the addition of an adjuvant to the spray solution for the proposed cro ps. **Table 3: Sum ma**  **ry of Proposed End -**  **Use Product and Target Pests.** Trade Name EPA Reg.

No. concentration Formulation Type Label Date Target Pests Sugar Apple, Cheri moya, Atemoya, Custard Apple, Ilama, Soursop, Biriba, Lychee, Longan, Spanish Lime, Rambutan, Pulasan,

Guava, Feijoa, Jaboticaba, Wax Jambu, Starfruit, Passionfruit, Persimmon, and Acerola Envidor® 2 SC Mticide 264 - 831 2 lb ai/gal SC not indicated broad mite, Carmine spider mite, citrus red mite, flat mite (black and red), persea mite, sixspotted mite, Texas citrus

mite, twospotted spider mite **Table 4:**  **Summary of Proposed Application Scenarios**  **.** App. Timing ; Type ; and Equip. Formulation

( EPA Reg. No. ) App. Rate

(lb ai/acre ) Max. # . App.

per Season Max. Seasonal App.

Rate (lb ai/acre ) PHI

(days) Use Directions and Limitations Sugar Apple, Cherimoya, Atemoya, Custard Apple, Ilama, Soursop, Biriba, Lychee, Longan, Spanish Lime, Rambutan, Pulasan, Guava, F eijoa, Jaboticaba, Wax Jambu, Starfruit, Passionfruit, Persimmon, and Acerola postemergence; foliar broadcast 2 lb ai /gal S C

( 264 - 831 ) 0.28 - 0. 31 1 0. 31 1 - Apply in a minimum of 5 0 GPA with ground equipment.

- Application through irrigation equipment and i n enclosed structures is prohibited. 

### 860.1300 Nature of the Residue **- Plants**  Table 5 below is a summary of the HED decisions concerning the residues of concern in primary crops, livestock, and rotational crops. For additional information, see the Executive Summary . **Table 5**  **: Residues of Concern for Tolerance Expression and Risk Assessm ent.**  Matrix Residues included in Risk Assessment Residues included in Tolerance Expression Pome Fruit, Tree Nut , and Hops spirodiclofen spirodiclofen Grape , Citrus F ruit, Stone Fruit, Berry (CG 13), and Tropical Fruit 1 spirodiclofen, BAJ 2510 spirodiclofen Livestock - Ruminants spirodiclofen, BAJ 2510 spirodiclofen, BAJ 2510 Livestock - Poultry no data submitted Rotational Crops no data submitted 1 BAJ 2510 is in cluded as a residue of concern in grape, citrus fruit, stone fruit, berry (CG 13), and tropical fruit due to the demonstrated (grape and citrus fruit) degradation of parent to BAJ 2510 during processing or due to the lack of data eliminat ing this possibili ty (stone fruit , berry (CG 13) , and tropical fruit). BAJ 2510 is only a residue of concern in the processed commodities of grape, citrus fruit, stone fruit, berry (CG 13), and tropical fruit. If processing data for the combined resi dues of spirodiclofen and BAJ 2510 are not available, then the dietary analysis should incorporate default processing factors. 

### 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 unnecessary .Spirodiclofen Summary of Analytical Chemistry and Residue Data D3 8 7 339

P age 7 of 13 

### 860.1340 Residue Analytical Methods **Tolerance Enforcement:** HED forwarded Bayer analy tical method 1 09351 t o FDA for inclusion in the PAM ( D368434, T. Bloem, 23 - Sep - 2009 ). Briefly , fruit samples are extracted with acetonitrile (ACN) :water (2:1; v:v) containing a small amount of aqueous 20% cysteine hydrochloride , filtered, and acidified with HCl . The extract is subjected to clean up on an ENVI carb cartridge prec onditioned with dichloromethane ( DCM ) , methanol , and water with residues eluted with DCM under vacuum. The resulting eluent is concentrated to dry ness and reconstituted in A C N and water for analysis by high - performance liquid chromatography /mass spectrome try

/mass spectrometry

( HPL C /MS/MS ) . The limit of quantitation ( L OQ ) was reported to be 0.01 ppm ( limits of detection ( LOD s) ranged from 0.001 - 0.006 ppm). Based on the similarities of the tolerance enforcement and the adequately validated data collection method (see below) , HED concludes that the current enforcement method is appropriate for enforcement of the tolerances recommended as part of the current petition. **Data Collection:** A summary of the lychee, sugar apple, and guava data collection methods are provided below. The studies indicated that the DCM partition provided sufficient cleanup to make the ENVI - carb cartridge cleanup step in the enforcement method unnecessary . Sugar Apple and Guava: The sample homogenates were extracted with ACN/wate r (2:1, v/v) mixed with a 20% aqueous cysteine hydrochloride solution. Following the addition of Celite, the extract was vacuum filtered, blended with an acetone/DCM solution (1:2, v/v), and vacuum filtered again. The filtrate was allowed to separate and the organic bottom layer was collected and diluted with acetone. The sample was then concentrated to dry ness and partitioned with hexane and two portions of ACN pre - saturated with hexane. All of the transfer solvents were collected, separated twice to c ollect the bottom ACN layers, and then concentrated to dry ness. The samples were partitioned with DCM and analy zed for residues of spirodiclofen per se using HPL C /MS/MS . Lyc hee: The samples homogenates w ere extracted with ACN/water (2:1, v/v) mixed wi th a 20% aqueous cysteine hydrochloride solution. Following the addition of Celite, the extract was vacuum filtered, rinsed, and brought to volume with the extraction solution. An aliquot of the sample was mixed with 1.2N HCl, diluted with water, and shaken. The diluted sample was partitioned with DCM and the lower organic phase was passed through sodium sulfate. The sodium sulfate was rinsed with DCM and evaporated to dry ness. The samples were partitioned with DCM and analy

zed for residues of spirodic lofen per se using HPL C /MS/MS . **860.1360 Multiresidue Methods** Spirodiclofen and BAJ 2510 were screened through the FDA MRM protocols. S ince both spirodiclofen and BAJ 2510 are not N - methylcarbamates, naturally fluorescent, acids, phenols, or substitute d ureas, testing through p rotocols A, B, and G is unnecessary . Protocol C modules DG1 and DG10 gave acceptable results for BAJ 2510 and spirodiclofen, respectively (both are GC/ECD sy stems). 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 (fortified orange samples) and F (fortified ground beef samples). SinceSpirodiclofen Summary of Analytical Chemistry and Residue Data D3 8 7 339

P age 8 of 13 

### 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). **860.1380 Storage Stability** The lychee, guava, and sugar apple s amples from the field trials were stored frozen for up to 3 50 days prior to analysis. As part of the lychee field trial study , the petitioner submitted storage stabili ty which indicate that residues of spirodiclofen per se are stable in/on lychee when stored frozen for 35 4 days. HED notes that these data did not include a zero day analysis as requested in the OPPTS 860.1380 guidelines. The petitioner previous ly submitted storage stability data which indicated that residues of spirodiclofen per se are stable when stored frozen for the following 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 supp ort the storage intervals and conditions for the lychee, guava, and sugar apple 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 Trials** 4 8332901.der, 48332902.der, and 48332903.der 

### Insupport of the proposed registration, the petitioner submitted f ield trial studies conducted with lychee (n=3; NAFTA Growing Zone 13) , sugar apple (n=3; NAFTA Growing Zone 13), and guava (n=3; NAFTA Growing Zone 13). Provided the label is revised to prohibit the addition of adjuvants to the spray

solution, the application scenario employed in the field trials supports the proposed application scenario. Residues of spirodiclofen per se were as follows (method and storage intervals are validated; see Table 6 for a summary ): lychee - 0.579 - 1.54 ppm; sugar apple

- 0.051 - 0.194 ppm; and guava - 0.033 - 0.247 ppm. The number and locations of the lychee, sugar apple, and guava field trials are adequate to support registration for these c rops ; HED notes that some of the trials were conducted at the same location but were consid ered separate trials due to different application days and due to the recognized difficulty in finding adequate field trial locations for these low - acreage cro ps. Residue - decline data were included as part of the lychee field trial study

and indicate d that per - trial average spirodiclofen residues increased slightly as the preharvest interval ( PHI) increased from 1 day (1.54 ppm) to 3 days (1.73 ppm) and then declined as the PHI

increased to 14 days (0.62 ppm). HED has previously

approved the following dat a translations (Reviewer = s Guide and Summary of HED ChemSAC Approvals for Amending Commodity Definitions [40 CFR ' 180.1(h)] and Crop Group/Subgroups [40 CFR ' 180.41], B. Schneider, 14 - June - 2002; see ChemSAC Database): lychee to longan, Spanish lime, rambutan, and pulasan; sugar apple to atemoya, custard apple, cherimoya, ilama, soursop, and birida; and guava to feijoa, jaboticaba, wax jambu, starfruit, passionfruit, and acerola. In addition, the ChemSAC previously approved theSpirodiclofen Summary of Analytical Chemistry and Residue Data D3 8 7 339

P age 9 of 13 

### translation of spirodiclofen guava residue data to persimmon provided the application scenario for each was identical (ChemSAC minutes of the 17 -Nov - 2010 meeting). Therefore, based on the available residue data and the OECD tolerance calculator, HED concludes that the following tole rances for residues of spirodiclofen per se are appropriate (see attachment 3 ; a revised Section F is requested): lychee - 4.0 ppm; longan - 4.0 ppm; Spanish lime - 4.0 ppm; rambutan - 4.0 ppm; pulasan - 4.0 ppm; sugar apple - 0.40 ppm; atemoya - 0.40 ppm ; custard apple - 0.40 ppm; cherimoya - 0.40 ppm; ilama - 0.40 ppm; soursop - 0.40 ppm; birida - 0.40 ppm; guava - 0.50 ppm ; feijoa - 0.50 ppm; jaboticaba - 0.50 ppm; wax jambu - 0.50 ppm; starfruit - 0.50 ppm; passionfruit - 0.50 ppm; acerola - 0.50 ppm; and persimmon - 0.50 ppm. **T able**  **6: Summary of**  **Spirodiclofen per se residue Data from the**  **Lychee , Sugar Apple, and Guava**  **Field Trials .**  Commodity Analyte Total App. Rate (lb ai/A) PHI

(days) Residue Levels ( spirodiclofen per se ; ppm) 1 n Sample Min. Sample

Max. LAFT 2 HAFT 2 Median Mean Std. Dev. Lychee fruit Spirodiclofen 0.3164 - 0.3212 1 3 0.579 1.54 0.657 1.54 0.955 1.05 0.449 Sugar apple fruit Spirodiclofen 0.3181 - 0.3196 1 3 0.051 0.194 0.095 0.138 0.122 0.118 0.022 Guava fruit Spirodiclofen 0.3161 - 0.3243 1 3 0.033 0.247 0.085 0.230 0.192 0.169 0.075 1 Except for sample min/max, values reflect per trial averages; n = no. of field trials. 2 LAFT = lowest - average - field - trial; HAFT = highest - average - f ield - trial. 

### 860.1520 Processed Food and Fe **ed** Based on Table 1 of OPPTS 860.1000, processing studies are not required for the proposed crops. **860.1850/860.1900 Confined and Field Accumulation in Rotational Crops** Since all of the requested crops are perennials, a discussion concerning the nature/magnitude of the residue in rotational crops is unnecessary .Spirodiclofen Summary of Analytical Chemistry and Residue Data D3 8 7 339

P age 10 of 13 

### 860.1550 Proposed/Recommended Tolerances Table 5 is a summary

of the proposed and recommended tolerance for residues of spirodiclofen per se . There are no Codex, Canadian, or Mexican max imum residue limits (MRL s) in/on the requested crops. Therefore , harmonization is not an issue for this petition. Inaccordance with the most recent guidance concerning tolerance expressions, HED recommends that the tolerance expression for 180.608(a)( 1) and 180.6(a)(2) be changed as indicated below. HED notes that this alteration in the tolerance expression does not necessitate a change in the currently

established or recommended tolerance levels. A revised Section F specifying the new tolerance expr ession , the currently established commodity

/tolerance levels, and the HED - recommended tolerance should be submitted. 180.608(a)(1): Tolerances are established for residues of spirodiclofen, including its metabolites and degradates, in or on the commodi ties listed below. Compliance with the following tolerance levels is to be determined by

measuring only spirodiclofen (3 - (2,4 - dichlorophenyl) - 2 - oxo - 1 - oxaspiro[4.5]dec - 3 - en - 4 - yl2,2 - dimethylbutanoate . 180.608(a) ( 2): Tolerances are established for residue s of spirodiclofen, including its metabolites and degradates, in or on the commodities listed below. Compliance with the following tolerance levels is to be determined by

measuring only spirodiclofen (3 - (2,4 - dichlorophenyl) - 2 - oxo - 1 - oxaspiro[4.5]dec - 3 - en - 4 - yl2,2 - dimethylbutanoate ) and its metabolite 3 - (2,4 - dichlorophenyl) - 4 - hydroxy- 1 - oxaspiro[4,5] dec - 3 - en - 2 - one . **Table 5**  **: Tolerance Sum**  **ma ry**  **.** Commodity Proposed

Tolerance (ppm) HED - Recommended

Tolerance (ppm) Comments Lychee 3.5 4.0 Based on the field tri al data and the OECD tolerance calculator, the appropriate tolerance for residues of spirodiclofen per se in/on these crops is 4.0 ppm. L ongan 3.5 4.0 Spanish lime 3.5 4.0 R ambutan 3.5 4.0 P ulasan 3.5 4.0 S ugar apple 0.45 0.40 Based on the field trial data and the OECD tolerance calculator, the appropriate tolerance for residues of spirodiclofen per se in/on these crops is 0.40 ppm. Atemoya 0.45 0.40 C ustard apple 0.45 0.40 C herimoya 0.45 0.40 I lama 0.45 0.40 S oursop 0.45 0.40 B iriba 0.4 5 0.40 G uava 0.45 0.50 Based on the field trial data and the OECD tolerance calculator, the appropriate tolerance for residues of spirodiclofen per se in/on these crops is 0.50 ppm. F eijoa 0.45 0.50 J aboticaba 0.45 0.50 W ax jambu 0.45 0.50 S tarfru it 0.45 0.50 P assionfruit 0.45 0.50 A cerola 0.45 0.50 P ersimmon 0.45 0.50 Attachment 1: Chemical Structures Attachment 2: Codex Attachment 3: Tolerance Calculation RDI: RAB1 Chemists ( 28 - Sep - 20 1 1 ) T. Bloem:S10945:Potomac Yard 1:703 - 605 - 0217:7509P:RABISpirodiclofen Summary of Analytical Chemistry and Residue Data D3 8 7 339

P age 11 of 13 

### Attachment 1: Chemical Structures

**Chem ical 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 HSpirodiclofen Summary of Analytical Chemistry and Residue Data D3 8 7 339

P age 12 of 13 

### Attachment 2: International residue L imit Status **Summary of US and International Tolerances a nd Maxim**  **um Residue Limits** Residue Definition

US Canada Mexico 2 Codex 3 40 CFR 180.608(a): spirodiclofen per se (3 - (2,4 - dichlorophenyl) - 2 - oxo - 1 - oxaspiro[4.5]dec - 3 - en - 4 - yl 2,2 - dimethylbutanoate Plants : 3 - (2,4 - dichlorophenyl) - 2 - oxo - 1 - oxaspiro[4.5]dec - 3 - e n - 4 - yl 2,2 - dimethylbutanoate Livestock: 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) Spirodiclofen The residue is fat soluble Tolerance/Maximum Residue Limit (ppm)

Commodity 1 US Canada Mexico 2 Codex 3 A cerola 0.45 none -- 2 none Atemoya 0.45 none -- 2 none B iriba 0.45 none -- 2 none C herimoya 0.45 none -- 2 none C ustard apple 0.45 none -- 2 none F eijoa 0.45 none -- 2 none G uava 0.45 none -- 2 none I lama 0.45 none -- 2 none J aboticaba 0.45 none -- 2 none L ongan 3.5 none -- 2 none Lychee 3.5 none -- 2 none P assionfruit 0.45 none -- 2 none P ersimmon 0.45 none -- 2 none P ulasan 3.5 none -- 2 none R ambutan 3.5 none -- 2 none S our sop 0.45 none -- 2 none Spanish lime 3.5 none -- 2 none S tarfruit 0.45 none -- 2 none S ugar apple 0.45 none -- 2 none W ax jambu 0.45 none -- 2 none Completed: M. Negussie; 06/23/2011 1 I ncludes only c ommodities 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 final ized by the CCPR and the CAC.Spirodiclofen Summary of Analytical Chemistry and Residue Data D3 8 7 339

P age 13 of 13 

### Attachment 3: Tolerance Calculation **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)** 1.540 0.138 0.230 0.955 0.122 0.085 0.657 0.095 0.192 3 0% **spirodiclofen guava**  **spirodiclofen lychee**  **US 1 x 0.32 lb ai/acre**  **US 1 x 0.32 lb ai/acre** 

3 0.657 1.540 0.955 1.051 0.449

3.152 **4** High uncertainty of MRL estimate due to small dataset.

1.000

1.540 2.847 3.152 0.095 0.138 0.122 0.118 0.022 1.000

0.138 0.205 0.355 0.355 **0.4** High uncertainty of MRL estimate due to small dataset. 3 0.085 3 0%

0.230 0.192 0.169 0.075 1.000

0.230 0.470 0.507 0.507 **0.5** High uncertainty of MRL estimate due to small dataset. 3 **spirodiclofen sugar apple**  **US 1 x 0.32 lb ai/acre** 

3 0%