Spirodiclofen Summary of Analytical Chemistry and Residue Data D387339

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UNITED STATES ENVIRONMENTAL PROTECTION AGENCY

WASHINGTON, D.C. 20460

OFFICE OF CHEMICAL SAFETY AND

POLLUTION PREVENTION

MEMORANDUM

Date: 15-October-2011

Subject: Spirodiclofen in/on 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. Summary

of Analytical Chemistry and Residue Data.

PC Code: 124871 DP Barcode: D387339

Decision No.: 443557 Registration No.: 264-831

Petition No.: 0E7820 Regulatory Action: Section 3 

Risk Assessment Type: not applicable Case No.: 7443

TXR 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 (RAB1/HED; 7509C)

Through: George F. Kramer, Ph.D., Senior Chemist

HED/RAB1 (7509P)

To: Barbara Madden/Laura Nollen (RM 05)

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-yl 2,2-

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 D387339

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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 nymphal 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 13-07B, 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 byproduct, and fat 

tolerance for the combined residues of spirodiclofen and BAJ 2510 are also established (0.02-0.1 

ppm). 

Proposed Application Scenarios: The petitioner 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, 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 requests a 

revised Section B which prohibits the addition of an adjuvant to the spray solution for the 

proposed crops. 

Nature/Magnitude 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/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. 

Nature of the Residue - Primary Crops: Based on the results of the citrus, grape, 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 previous 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 

per 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 grape, 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. Based on the results of the 

grape and orange processing studies, HED requests 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 D387339

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Magnitude of the Residue - Primary Crops: In support of the proposed registration, 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): 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 crops. Based on Table 1 of OPPTS 860.1000, 

processing 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, based 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 analytical method 109351 

was appropriate for enforcement of the hop, citrus, grape, pome fruit, stone fruit, and tree nut 

tolerances and forwarded this method to Food and Drug Administration (FDA) for inclusion in 

the Pesticide Analytical Manual (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 recommended 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 substituted 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)

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 (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 D387339

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Recommendations: Provided revised Sections B and F are submitted, HED concludes that the 

residue chemistry database supports an unconditional 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 ppm; acerola - 0.50 ppm; and persimmon - 0.50 ppm.

In accordance 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 expression, the currently established commodity/tolerance levels,

and the HED-recommended tolerances 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-yl 2,2-dimethylbutanoate).

180.608(a)(2): 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-yl 2,2-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 crops. 

Revised Section F.
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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 nymphal 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: Nomenclature.

Spirodiclofen

O

O

Cl

Cl

O

O H3C

H3C

H3C

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-dimethylbutanoate

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: Physicochemical 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) 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 10-7Pa

Dissociation 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 nm
Spirodiclofen Summary of Analytical Chemistry and Residue Data D387339

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860.1200 Directions for Use

The petitioner proposed use directions for application of Envidor® 2 SC Miticide (suspensionconcentrate; 2 lbs ai/gallon; EPA Reg. No. 264-831) 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. Table 3 is a summary of 

the proposed formulation and target pests and Table 4 is a summary of the proposed application 

scenario. HED requests a revised Section B which prohibits the addition of an adjuvant to the 

spray solution for the proposed crops. 

Table 3: Summary of Proposed End-Use Product and Target Pests.

Trade Name EPA Reg. 

No. concentration FormulationType Label Date Target Pests

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

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, 

Feijoa, Jaboticaba, Wax Jambu, Starfruit, Passionfruit, Persimmon, and Acerola

postemergence; 

foliar broadcast

2 lb ai/gal SC

(264-831)

0.28-0.31 1 0.31 1

-Apply in a minimum of 50 GPA with 

ground equipment.

-Application through irrigation equipment 

and in 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 Assessment.

Matrix Residues included in

Risk Assessment

Residues included in

Tolerance Expression

Pome Fruit, Tree Nut, and Hops spirodiclofen spirodiclofen

Grape, Citrus Fruit, Stone Fruit, Berry (CG 13), and Tropical Fruit1

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 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). 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 residues 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. 
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860.1340 Residue Analytical Methods

Tolerance Enforcement: HED forwarded Bayer analytical method 109351 to 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 ENVIcarb cartridge preconditioned with dichloromethane (DCM), methanol, and water with residues 

eluted with DCM under vacuum. The resulting eluent is concentrated to dryness and 

reconstituted in ACN and water for analysis by high-performance liquid chromatography/mass 

spectrometry/mass spectrometry (HPLC/MS/MS). The limit of quantitation (LOQ) was reported 

to be 0.01 ppm (limits of detection (LODs) 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/water (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 dryness and partitioned with 

hexane and two portions of ACN pre-saturated with hexane. All of the transfer solvents were 

collected, separated twice to collect the bottom ACN layers, and then concentrated to dryness. 

The samples were partitioned with DCM and analyzed for residues of spirodiclofen per se using

HPLC/MS/MS. 

Lychee: The samples homogenates were extracted with ACN/water (2:1, v/v) mixed with 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 dryness. The samples were partitioned 

with DCM and analyzed for residues of spirodiclofen per se using HPLC/MS/MS. 

860.1360 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 

substituted 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 

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 (fortified orange samples) and F (fortified ground beef samples). Since 
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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 samples from the field trials were stored frozen for up to 350

days prior to analysis. As part of the lychee field trial study, the petitioner submitted storage 

stability which indicate that residues of spirodiclofen per se are stable in/on lychee when stored 

frozen for 354 days. HED notes that these data did not include a zero day analysis as requested in 

the OPPTS 860.1380 guidelines. The petitioner previously 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 

support 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

48332901.der, 48332902.der, and 48332903.der

In support of the proposed registration, the petitioner submitted field 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 crops; HED notes that 

some of the trials were conducted at the same location but were considered separate trials due to 

different application days and due to the recognized difficulty in finding adequate field trial 

locations for these low-acreage crops. Residue-decline data were included as part of the lychee 

field trial study and indicated 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 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 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 
Spirodiclofen Summary of Analytical Chemistry and Residue Data D387339

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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 

tolerances 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. 

Table 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.

LAFT2 HAFT2 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-field-trial.

860.1520 Processed Food and Feed

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 D387339

Page 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 maximum residue limits (MRLs) in/on the 

requested crops. Therefore, harmonization is not an issue for this petition. 

In accordance 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 expression, 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 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-yl 2,2-dimethylbutanoate.

180.608(a)(2): 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-yl 2,2-dimethylbutanoate) and its metabolite 3-(2,4-dichlorophenyl)-4-hydroxy-1-oxaspiro[4,5]

dec-3-en-2-one.

Table 5: Tolerance Summary.

Commodity Proposed 

Tolerance (ppm)

HED-Recommended 

Tolerance (ppm) Comments

Lychee 3.5 4.0

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 4.0 ppm.

Longan 3.5 4.0

Spanish lime 3.5 4.0

Rambutan 3.5 4.0

Pulasan 3.5 4.0

Sugar 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

Custard apple 0.45 0.40

Cherimoya 0.45 0.40

Ilama 0.45 0.40

Soursop 0.45 0.40

Biriba 0.45 0.40

Guava 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.

Feijoa 0.45 0.50

Jaboticaba 0.45 0.50

Wax jambu 0.45 0.50

Starfruit 0.45 0.50

Passionfruit 0.45 0.50

Acerola 0.45 0.50

Persimmon 0.45 0.50

Attachment 1: Chemical Structures

Attachment 2: Codex

Attachment 3: Tolerance Calculation

RDI: RAB1 Chemists (28-Sep-2011)

T. Bloem:S10945:Potomac Yard 1:703-605-0217:7509P:RABI
Spirodiclofen Summary of Analytical Chemistry and Residue Data D387339

Page 11 of 13

Attachment 1: Chemical Structures

Chemical Name 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 H3C

H3C

H3C

BAJ 2510

3-(2,4-dichlorophenyl)-4-hydroxy-1-oxaspiro[4.5]dec-3-en-2-

one O

Cl

Cl

O

HO

3-OH-enol

3-OH-enol spirodiclofen

O

Cl

Cl

O

HO

HO

4-OH-enol

4-OH-enol spirodiclofen

O

Cl

Cl

O

HO

HO
Spirodiclofen Summary of Analytical Chemistry and Residue Data D387339

Page 12 of 13

Attachment 2: International residue Limit Status

Summary of US and International Tolerances and Maximum Residue Limits 

Residue Definition

US Canada Mexico2 Codex3

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-en-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-en2-one, 3-(2,4- dichlorophenyl)-4-hydroxy-(9CI)

Spirodiclofen The 

residue is fatsoluble

Tolerance/Maximum Residue Limit (ppm)

Commodity1 US Canada Mexico2 Codex3

Acerola 0.45 none --

2

none

Atemoya 0.45 none --

2

none

Biriba 0.45 none --

2

none

Cherimoya 0.45 none --

2

none

Custard apple 0.45 none --

2

none

Feijoa 0.45 none --

2

none

Guava 0.45 none --

2

none

Ilama 0.45 none --

2

none

Jaboticaba 0.45 none --

2

none

Longan 3.5 none --

2

none

Lychee 3.5 none --

2

none

Passionfruit 0.45 none --

2

none

Persimmon 0.45 none --

2

none

Pulasan 3.5 none --

2

none

Rambutan 3.5 none --

2

none

Soursop 0.45 none --

2

none

Spanish lime 3.5 none --

2

none

Starfruit 0.45 none --

2

none

Sugar apple 0.45 none --

2

none

Wax jambu 0.45 none --

2

none

Completed: M. Negussie; 06/23/2011

1

I ncludes 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.
Spirodiclofen Summary of Analytical Chemistry and Residue Data D387339

Page 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%