Spirodiclofen Summary of Analytical Chemistry and Residue Data D363343

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UNITED STATES ENVIRONMENTAL PROTECTION AGENCY

WASHINGTON, D.C. 20460

OFFICE OF 

PREVENTION, PESTICIDES

AND TOXIC SUBSTANCES

MEMORANDUM

Date: 23-September-2009

Subject: Spirodiclofen in/on Avocado, Black Sapote, Canistel, Mamey Sapote, Mango, 

Papaya, Sapodilla, and Star Apple. Summary of Analytical Chemistry and 

Residue Data.

PC Code: 124871 DP Barcode: D363343

Decision No.: 404221 Registration No.: 264-831

Petition No.: 8F7500 Regulatory Action: Section 3 

Risk Assessment Type: not applicable Case No.: none

TXR 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 (RABI/HED; 7509C)

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

HED/RABI (7509P)

To: John Hebert/Rita Kumar (RM 07)

Registration Division (RD; 7505P) 

Bayer CropScience (Research Triangle Park, NC) proposed the establishment of permanent 

tolerances for residues of spirodiclofen (3-(2,4-dichlorophenyl)-2-oxo-1-oxaspiro[4.5]dec-3-en4-yl 2,2-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 ppm
Spirodiclofen Summary of Analytical Chemistry and Residue Data D363343

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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, and hops with tolerances for residues of spirodiclofen per se of 0.10-

30 ppm; milk and ruminant meat, meat byproducts, 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 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, 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 (e. g.; crop-oil 

concentrate, nonionic surfactant, methylated seed oil) 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 adjuvants, HED requests a revised Section B prohibiting the 

addition of adjuvants 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

PHI1

(days) Comments

Avocado, Black Sapote, Canistel, Mamey Sapote, Mango, Papaya, Sapodilla, 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.

●Maximum seasonal application rate - 0.31 lb ai/acre.

●Label states the following pests are controlled - Avocado 

brown mite, Avocado red mite, Broad mite, Carmine spider 

mite, Citrus red mite, Flat mite (black and red), Mango spider 

mite, Papaya Leaf edgeroller mite, Persea mite, Sixspotted 

mite, Texas citrus mite, and Twospotted spider mite.

1

 PHI = preharvest interval.

Nature of the Residue - Plants: Based on the results of previously submitted apple and grape 

processing studies and citrus, grape, and apple metabolism studies (D285249, T. Bloem, 18-Apr2005; 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 concern 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 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 commodities for apple and grape.
Spirodiclofen Summary of Analytical Chemistry and Residue Data D363343

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HED determined that these conclusions may be translated to the currently requested crops. 

Therefore, 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 the free enol 

metabolite (BAJ 2510); hydroxylation of BAJ 2510 on the cyclohexyl ring to form 3-OH-enol 

and 4-OH-enol metabolites; and cleavage of the enol ring structure to form 2,4-dichloromandelic 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 demonstrate 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 conjugate; ≤12% TRR).

Magnitude of the Residue - Plants: In support 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. Provided 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 tolerance of 

1.0 ppm, for residues of spirodiclofen per se, is appropriate. Based on guidance from the HED 

Chemistry Science Advisory Council (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 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 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. 

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 data collection method and the tolerance enforcement method and since the 

tolerance enforcement method has 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.
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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 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 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 (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).

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. 

Recommendations: Provided the petitioner submits revised Sections B and F, HED concludes 

that the residue chemistry database supports an unconditional registration and establishment of 

the following permanent tolerances for residues of spirodiclofen per se: Avocado - 1.0 ppm, 

Black sapote - 1.0 ppm, Canistel - 1.0 ppm, Mamey sapote - 1.0 ppm, Mango - 1.0 ppm, Papaya -

1.0 ppm, Sapodilla - 1.0 ppm, and Star apple - 1.0 ppm. 

Summary of Residue Chemistry Deficiencies:

Revised Section B

Revised Section F
Spirodiclofen Summary of Analytical Chemistry and Residue Data D363343

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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 2 and 3

are summaries of spirodiclofen nomenclature and physical chemical properties, respectively.

Table 2: 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 3: 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 D363343

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860.1200 Directions for Use

The petitioner 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, methylated seed oil) 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 adjuvants, HED requests a revised Section B 

prohibiting the addition of adjuvants to the spray solution. 

860.1300 Nature of the Residue - Plants

Based 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-Oct2007; 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 concern 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 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 commodities for apple and grape.

HED has determined that these conclusions may be translated to the currently requested crops. 

Therefore, 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 the free enol 

metabolite (BAJ 2510); hydroxylation of BAJ 2510 on the cyclohexyl ring to form 3-OH-enol 

and 4-OH-enol metabolites; and cleavage of the enol ring structure to form 2,4-dichloromandelic 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 demonstrate 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% 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 acidcyclohexylester compounds (free and conjugated; ≤9% TRR), and 2,4-dichloro-mandelic acid 

(free and conjugate; ≤12% TRR).
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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. 

860.1340 Residue Analytical Methods

Data Collection: The avocado field trial samples were analyzed for residues of spirodiclfen per 

se using a liquid chromatograph/mass spectrometer/mass spectrometer (LC/MS/MS) method. 

Briefly, pitted homogenized samples were extracted by blending with acetonitrile (ACN):water 

(2:1; v:v) containing a small amount of aqueous 20% cysteine hydrochloride. Isotopically

labeled internal standard were added and the extracts were centrifuged, filtered through a nylon 

syringe filter, and analyzed via LC/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 collection 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 (LLMV), 

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 analytical method 109351 to FDA for inclusion 

in the PAM (D368434, 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 dryness and reconstituted in ACN and water for analysis by LC/MS/MS. 

The LOQ 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 has been validated on a fruit crop, 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%) 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).
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860.1380 Storage Stability

The avocado fruit samples from the field trials were stored frozen for up to 282 days prior to 

analysis. 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 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 Trials

47630101.der.doc

In support 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 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 vlaidated). 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 tolerance of 1.0 ppm, for residues of spirodiclofen per se, is 

appropriate (see attachment 3). Based on 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. Schneider; 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. 

Avocado (47630101.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 LLMV, 

the LOQ is 0.01 ppm (residues in controls <LOQ). The statistically determined limit of detection 
Spirodiclofen Summary of Analytical Chemistry and Residue Data D363343

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(LOD) is 0.0017 ppm (standard deviation at 0.01 ppm multiplied by the one-tailed 99% t-stat). 

The storage intervlas were also 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: Summary of Avocado Residue Data.

Commodity Total App. Rate 

(lb ai/A); Spray Vol.

PHI 

(days)

Residue Levels (ppm)1

n Min. Max. HAFT2 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 Processed 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 discussion 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 Section F should be submitted. There are no Codex, Canadian, or Mexican 

maximum residue limits (MRLs) in/on the requested crops. Therefore, harmonization is not an 

issue for this registration. 

Table 5: Tolerance Summary.

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:RAB1
Spirodiclofen Summary of Analytical Chemistry and Residue Data D363343

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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 D363343

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Attachment 2: International residue Limit Status

INTERNATIONAL RESIDUE LIMIT STATUS

Chemical Name: 

3-(2,4-dichlorophenyl)-2-oxo-1-

oxaspiro[4,5]dec-3-en-4-yl 2,2-

dimethylbutanoate

Common Name:

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: 363343

Other Identifier:

Residue definition: N/A Reviewer/Branch: Tom Bloem/RAB1

Residue definition: spirodicl0fen

Crop (s) MRL (mg/kg) Crop(s) Tolerance (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.
Spirodiclofen 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

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

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

Percentiles

Concentrations

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