Acetamiprid Summary of Analytical Chemistry and Residue Data DP#s: 364833 & 366269

Page 1 of 38 UNITED STA

TES ENVIRONMENTA L PROTECTION AGENCY WASHINGTON, D.C. 20460 OFFICE OF PREVENTION, PESTICIDE AND TOXIC SUBSTANCES MEMORANDUM Date: October 14, 2009 SUBJECT: Acetamiprid. Request for L abel Amendments for Ne w Use s o n Clover ; Small

Vine Climbing Fruits, except Kiwi f ruit, Subgroup 13 - 07F (amending grape use) ; Greenhouse - grown Tomatoes ; and a Regional Registration for Tea . Summary of Analy tical Chemistry

and Residue Data . PC Code: 099050 DP Barcode: D 364833 , D366269 Decision No.: 408298 Registration No s . : 8033 - 23, 8033 - 36, 8033 - 94 Petition No.: 9E7544 Regulatory Action: Amended Section 3 & Regional Registration for Tea Risk Assessment Type: NA Case No.: NA T XR No.: NA CAS No.: 135410 - 20 - 7 MRID No s .: 47716901, 47716902,

47716903 , 47781201 40 CFR: § 180. 578 FROM: Dennis McNeilly , Chemist

Risk Assessment Branch I I (RAB2) Health Effects Division (HED) (7509P) THROUGH William Drew, Chemist

Risk Assessment Branch I I (RAB2) Health Effects Division (HED) (7509P) and Christina Swartz, Chief Richard A. L oranger, Ph.D., Senior Scientist Risk Assessment Branch I I (RAB2) Health Effects Division (HED) (7509P) TO: Barbara Madden , Team 0 5

RIMUERB Registration Division (RD) (7505P) This document wa s originally prepared und er contract by Dynamac Corporation ( 1901 Research Boulevard, Suite 220 ; Rockville, MD 20850 ) . The document has been reviewed by the Health Effects Division (HED) and revised to reflect current Office of Pesti cide Programs (OPP) policiesAcetamiprid Summary of Analytical Chemistry and Residue Data DP#: 364833

Page 2 of 38 Executive Summary Acetamiprid is a selective insecticide intended for use against various sucking/chewing insect pests that feed upon field, fruit , and vegetable crops. Acetamiprid is registered for foliar application to cotton, leafy vegetables, col e (

Brassica ) vegetables, fruiting vegetables, tuberous and corm vegetables, citrus fruits, pome fruits, cucurbit vegetables, stone fruits, tree nuts , berries, bulb vegetables, succulent legume vegetables and grapes, and for seed treatment of canola and mus tard seed s . The Interregional Research Project Number 4 (IR - 4) has submitted amended Section 3 registration request s for new use s of acetamiprid on clover grown for seed , small vine climbing fruits, except kiwifruit, subgroup 13 - 07F (amending established grape uses), greenhouse - grown tomatoes , and tea . The end - use products associated with this action include: (i) Assail® 30 SG In secticide (EPA Reg. No. 8033 - 36), a 30% active ingredient ( ai ) soluble granule (SG) formulation; (ii) Assail® 70WP Insecticide ( EPA Reg. No. 8033 - 23), a 70% ai wettable powder (WP) formulation; and (iii) Tristar® 30 SG Insecticide (EPA Reg. No. 8033 - 94), a 30% ai SG formulation. For clover, Assail® 30 SG and Assail® 70WP are proposed for a single postemergence broadcast foliar app lication at a maximum of 0.075 lb ai/A with a 28 - day preharvest interval (PHI) ; the proposed use is limited to clover grown in ID, OR, and WA only . For grapes, a change to the registered use pattern is proposed. The current label permits up to two foliar applications on grapes at 0.05 lb ai/A/application for a maximum seasonal rate of 0.1 lb ai/A with a 7 - day PHI . The requested new use on grapes (and small vine climbing fruits, except kiwifruit, subgroup 13 - 07F ) will permit up to two foliar applications of Assail® 30SG and Assail® 70WP at 0.1 lb ai/A/application for a seasonal rate of 0.2 lb ai/A with a 3 - day PHI . For tomatoes, a new use on greenhouse - grown tomatoes is proposed. The current Assail® 30 SG and Assail® 70WP label s permit up to four foliar a

pplications on field - grown tomatoes at 0.075 lb ai/A/application for a maximum seasonal rate of 0.3 lb ai/A with a 7 - day PHI . The requested new use on tomatoes will add a greenhouse use pattern using Tristar® 30 SG , with a maximum of two applications at 0. 075 lb ai/A/application (based on 10,000 plants per acre) for a maximum seasonal rate of 0.15 lb ai/A, applied via chemigation with a 1 - day PHI . No use directions were proposed for the domestic use on tea grown in South Carolina. The following GAP inform ation was provided for the 20% SP formulation in Japan: one application at 0.10 - 0.40 kg ai/ha applied in 2000 - 4000 L/ha, with a 14 - day

PHI . Application rate GAP information for India were not provided ; however , the residue data conducted in In dia were a single application of 0.022 lb ai/A (0.025 kg ai/ha) or 0.045 lb ai/A (0.050 kg ai/ha) . The shoots along with bud are (reportedly ) ty pically harvested at a 7 - day PHI in India . Concurrently , IR - 4 ha s proposed the establishment of permanent tole rances for residues of acetamiprid in or on the raw agricultural commodities (RACs) listed below.

Clover, forage ................................ ........................... 0 .10 ppm Clover, hay ................................ ............................... 0.01 ppm Fruit, small, vine climbing, except fuzzy kiwifruit, subgroup 1 3 - 07F ................................ ................... 0. 3 5 ppm Tea ................................ ................................ ........ 50.0 ppmAcetamiprid Summary of Analytical Chemistry and Residue Data DP#: 364833

Page 3 of 38 Tolerances have been esta blished under 40 CFR §180.578 ( a)( 1 ) for residues of the insecticide acetamiprid , ranging from 0.01 to 20 ppm in/on canola seed, cotton matrices , and various fruits , nuts, and vegetables. Tolerances for the combined residues of acetamiprid and N1 - [(6 - chlo ro - 3 - py ridyl)methyl] - N2 - cyano - acetamidine have also been established for livestock commodities (ruminants and poultry

) ranging from 0.01 to 0.20 ppm under 40 CFR §180.578 ( a)( 2 ) . Compliance with the tolerance levels listed in 40 CFR §180.578 is to be deter mined by measuring only

acetamiprid for plant commodities , and acetamiprid and its IM - 2 - 1 metabolite for animal commodities as quantitated by the GC/ECD and LC /MS/MS analy tical enforcement methods. HED has previously

determined that the nature of the res idue in plants and animals is adequately understood. T he residue of concern in plants is acetamiprid for both tolerance enforcement and risk assessment purposes . The residues of concern in livestock commodities for tolerance expression are acetamiprid plus its IM - 2 - 1 metabolite. For the purpose of risk assessment, the residues of concern in livestock commodities (except ruminant muscle) are acetamiprid plus its IM - 2 - 1 metabolite. In ruminant muscle, the residues of concern for risk assessment are acetam iprid plus IM - 2 - 1 plus IM - 2 - 1 - amide. The proposed use on clover could theoretically lead to the secondary

transfer of acetamiprid residues of concern to beef and dairy cattle from the feeding of clover forage, hay , and silage. However, the proposed use o n clover grown for seed is restricted to clover grown in ID, OR, and WA and the residues in or on the animal feed items are very low . Therefore, HED does not believe that the proposed use on clover would significantly increase the dietary

burdens, and the established tolerances in milk, meat, and meat by products need not be reassessed for the purpose of this petition. Adequate gas chromatograph with electron capture detection (GC/ECD) and high performance liquid chromatography

with ultraviolet detection ( HPL C/UV) residue analy tical methods are available for the enforcement of established tolerances on plant commodities . The method limits of quantitation (L OQ) are 0.01 ppm for vegetables and non - citrus fruits (GC/ECD), and 0.050 ppm for citrus fruits (HPL C /UV). A secondary liquid chromatography with tandem mass spectrometric detection ( LC /MS/MS ) method , designated by the petitioner as an alternative to the established GC/ECD tolerance enforcement method, has been determined suitable for tolerance enforceme nt, and confirmatory analy sis of vegetables and non - citrus fruits. The GC/ECD method or LC /MS/MS Method #KP - 216R1 (or its modification ) w as used for the analy sis of samples from the clover, grape, and tomato field trials. A cceptable recoveries were obtai ned in method validation efforts conducted prior to the analy sis of field trial samples . In a Japanese study , dried green tea leaves and brewed tea were analy zed for combined residues of acetamiprid and metabolites convertible to 6 - chloronicotinic acid (M etabolite I C - 0) using a common moiety

GC/ECD method. Briefly , dried tea leaves were homogenized, soaked in water, and then extracted with methanol. Brewed tea was simply filtered. The resulting extracts/filtrates were partitioned with hexane, and the aq ueous layer was subjected to base hydroly sis. Acetamiprid and metabolites were then converted to 6 - chloronicotinic acid by oxidation, then methylated (procedure not specified) and purified by silica column chromatography

prior to GC/ECD analy sis. The rep orted method L OD was 0.05 ppm as acetamiprid. InIndia , samples of green shoots, dried black tea leaves, brewed tea, and spent leaves were analy

zed for residues of acetamiprid using an HPL C/UV method. The reported L ODAcetamiprid Summary of Analytical Chemistry and Residue Data DP#: 364833

Page 4 of 38 was also 0.05 ppm. Adequate multire sidue methods testing data have been submitted. These data indicate that the multiresidue methods are not appropriate for determining residues of acetamiprid. The available storage stability data for acetamiprid on representative crops , and the concurr ent storage stability

data for clover and tomato are adequate to support the submitted clover, grape, tomato , and tea field trials. The use pattern of the clover field trials adequately reflects the proposed label use pattern with the exception of the PHI for hay . The available field trial data indicate a regional tolerances for residues of acetamiprid in clover forage at 0.10 ppm and clover hay at 0.01 ppm , are appropriate . However, the submitted clover field trial data are not completely adequate to satisfy data requirements. The three clover field trials were all conducted in Zone 11 (OR) at the same location and within a very short time period of each other. Two additional clover field trials are required , as confirmatory data . Inaddition, the sub mitted resid u e data included field trial data for only the 70WP formulation. However, since the requested PHI is for 28 day s (generally

bridging data are required if the proposed PHI is less than or equal to 7 day s) , additional residue chemistry field tri al data are not required to support registration of the 30SG formulation . U se on clover grown for seed is to be limited to clover grown in ID, OR, and WA. Since the residue chemistry data submitted for clover hay reflect PHI s of between 56 - 63 day s, the P HIfor clover should be increased to 56 day s for any crop harvest ed as clover hay . The submitted grape resid u e data included field trial data for only the 70WP formulation (the original field trials also used a 70WP formulation). Since the requested PHI for grape is for 3 day s, additional residue chemistry field trial data are needed to support registration of the 30SG formulation. As a condition of registration, HED requests that three side - by- side field trials be conducted and submitted to determine if residues are comparable for the two different formulations. In addition, the submitted grape field trials were not conducted using an adjuvant . The label for Assail® 30SG (EPA Reg. No. 8033 - 36) should be revised to remove the use of a spreader, methylat ed seed oil or crop oil f rom the product label , unless an adjuvant is used in the side - by- side testing. The number and locations of the field trials for the 70WP formulation are in accordance with OPPTS Guideline 860.1500 for grapes, and the use pattern o f the field trials reflects the use pattern proposed for grapes ( and o ther c limbing v ine s mall f ruits , e xcept f

uzzy k iwifruit , within s ubgroup 13 - 07F) , except for the adjuvant use. As the representative crop of the fruit, small, vine climbing, except fuzz y kiwifruit, subgroup 13 - 07F, the available grape field trial data from the current submission, which reflect a higher seasonal rate and a shortened PHI from that which is currently registered, will support a tolerance for residues of acetamiprid in “ fruit , small, vine climbing, subgroup 13 - 07F, except fuzzy kiwifruit ” at 0.35 ppm . The established individual tolerance for grape at 0.20 ppm should be concomitantly removed upon establishment of the s ubgroup 13 - 07F tolerance . The application rate used in the submitted tomato residue d ata for the proposed greenhouse use was 2x the proposed seasonal rate for the greenhouse tomato use . The three trials conducted are adequate with respect to the number of trials. Although the greenhouse trials were conducted at a 2x application rate , no additional residue data will be required to support the proposed greenhouse use pattern for tomatoes provided the use is limited to the 70WP product (conditional data needed for SG formulation) . The available tomato greenhouse trial data indicate that theAcetamiprid Summary of Analytical Chemistry and Residue Data DP#: 364833

Page 5 of 38 established tolerance for residues of acetamiprid in fruiting vegetables (Crop Group 8) at 0.20 ppm will not be exceeded following applications of the Assail 70WP formulation of acetamiprid according to the use patterns of the t omato greenhouse trials. No residue data were provided for the proposed use of Tristar® 30SG on greenhouse tomatoes, the only formulation requested for this use on greenhouse tomatoes. HED does have side - by- side formulation trials (WP and soluble liquid formulation) for acetamiprid in undelinted cottonseed and cotton gin by products. These data indicate that residue levels are comparable for the two different formulation, i.e., WP and soluble liquid. In view of these data and the 70WP data reflecting 2x the seasonal rate , HED requests submission of only one side - by- side formulation trial (rather than the normal three side by- side trials) to support the use of Tristar® 30SG on greenhouse tomatoes as a condition of registration . The submitted magnitude of the residue data for tea reflect application of a 20% SP formulation of acetamiprid to green tea grown in Japan at 0.13 lb ai/A (0.15 kg ai/ha) and 0.27 lb ai/A (0.30 kg ai/ha) and to black tea grown in India at 0.022 lb ai/A (0.025 kg ai/ha) and 0.045 lb ai/A (0.050 kg ai/ha). Samples of tea leaves (and shoots) were harvested at PHI s of 7, 14, and 21 day s in the Japan study

and 0, 1, 3, 5, 7, 9, 11, 15, and 21 day s in the India study and were processed into dried tea leaves and brewed tea; spent tea leaves were also analy zed in the India study . Acceptable methods were used for quantitating residues of acetamiprid and metabolites determined as acetamiprid . No U.S. residue field trial data were submitted and proposed domestic use directions were not prov ided. At least one U.S. field trial study is required to establish a tolerance for domestic use of acetamiprid on tea. At this time HED can recommend for a 50 ppm tolerance on tea with no U.S. registration. An acceptable grape processing study was previ ously

reviewed, which reported processing factors of 1.5x for juice and 0.9x for raisins. Based on these data, no tolerance s are needed for juice or raisins as a result of the proposed use , because any residues in these commodities are expected to be less than the RAC tolerance. An acceptable tomato processing study was also previously

reviewed, which reported processing factors of 1.4x for puree and 3.0x for paste. Based on the observed processing factor of 3.0x and a HAFT of 0. 1 ppm, a tolerance of 0.4 0 ppm w as established for residues of acetamiprid in tomato paste. A tolerance was not needed for puree because any expected residues in puree would be less than the RAC tolerance. The proposed use on greenhouse - grown tomatoes will not change the expecte d residues in puree or paste. An acceptable confined rotational crop study is available. HED has determined that the residue of concern in rotational crops is parent only , and that tolerances would not be needed on rotational crops . The available conf ined rotational crop data indicate that field rotational crop studies and label restrictions for rotational crops are not required to support the proposed uses. An analy tical standard for acetamiprid is currently available in the National Pesticide Standa rds Repository . However, analy tical standard s for the IM - 2 - 1 and IM - 2 - 1 - amide metabolites are not available at the Repository . Analy tical reference standards of these metabolites should be supplied and supplies replenished as requested by the Repository . Regulatory Recommendations and Residue Chemistry DeficienciesAcetamiprid Summary of Analytical Chemistry and Residue Data DP#: 364833

Page 6 of 38 HED has examined the residue chemistry database for acetamiprid. Pending submission of revised Section B (see requirements under Directions for Use) and analy tical re ference standards (see requirements under Submittal of Reference Standards ) , there are no residue chemistry issues that would preclude granting a conditional registration for the requested uses of acetamiprid . The data that HED recommends be required as a condition of registration are specified below. Provided that the forthcoming human health risk assessment does not identify any issues of concern, the submitted dat a support the establishment of permanent tolerances for acetamiprid , including its metabol ites and degradates, under 40 CFR §180.578 , as listed below. Compliance with tolerance levels specified below is to be determined by measuring acetamiprid only . Clover, forage * ................................ ......................... 0 .10 ppm Clover, hay * ................................ ............................. 0.01 ppm Fruit, small, vine climbing, subgroup 1 3 - 07F , except fuzzy

kiwifruit ................................ ......... 0. 3 5 ppm Tea* * ................................ ................................ ...... 50.0 ppm * Tolerances with regional restrictions [40 CFR §180.578 (c)]. ** Tolerance without a U.S. registration. The established individual tolerance for grape at 0.20 ppm should be conco mitantly removed upon establishment of the subgroup 13 - 07F tolerance . No change is needed with regard to the established tolerance for residues of acetamiprid in fruiting vegetables (Crop Group 8) at 0.20 ppm as a result of adding greenhouse use on tomatoes. 860.1200 Directions for Use Because the grape field trial data submitted with this petition did not reflect the use of a surfactant in the application spray s, the label directions regarding use of a spreader, methylated seed oil or crop oil should be removed from the product label of Assail® 30SG (EPA Reg. No. 8033 - 36). The PHIfor clover harvested for hay should be increased to 56 day s on the 30SG and 70WP labels. Use directions for the domestic use of acetamiprid on tea were not submitted. HED cannot evaluate the data without proposed use directions for acetamiprid use on tea in South Carolina . GAP information was provided for Japan and India . The use directions are adequate to establish a tolerance without U.S. registrations (an “ import ” tole rance). 860.1650 Submittal of Analy tical Reference Standards Analy tical standard s for the IM - 2 - 1 and IM - 2 - 1 - amide metabolites are not available at the Repository and should be supplied. The reference standards should be sent to th e Analy tical Chemistry

L ab, which is located at Fort Meade, to the attention of Theresa Cole at the following address:Acetamiprid Summary of Analytical Chemistry and Residue Data DP#: 364833

Page 7 of 38 USEPA National Pesticide Standards Repository /Analy tical Chemistry

Branch/OPP 701 Mapes Road Fort George G. Meade, MD 20755 - 5350 (N ote that the mail will be returned if the extended zip code is not used.) 860.1550 Proposed Tolerances The final tolerances for subgroup 13 - 07F should reflect the correct commodity definition as specified in Table 8. A revised Section F is no needed for this minor change. The established individual tolerance for grape at 0.20 ppm should be concomitantly removed with establishment of the subgroup 13 - 07F tolerance . Conditional Data Requirements

 Two clover field trials reflecting the same use pattern uti lized in the submitted studies.  Three side - by- side field trials on grapes to demonstrate that residues from the 30SG formulation are comparable to or less than those from the 70WP product. The spray in the plots for the SG formulation should contain adjuv ant (spreader, methylated seed oil, or crop oil) if a label statement recommending such additives is desired.  One side - by- side greenhouse trial on tomatoes to demonstrate that residues from the SG formulation are comparable to or less than those from the 7 0WP product. Background The nomenclature of acetamiprid and its metabolites is summarized in Table 1, and the phy sicochemical properties of acetamiprid are summarized in Table 2.Acetamiprid Summary of Analytical Chemistry and Residue Data DP#: 364833

Page 8 of 38 T able 1. Acetamiprid Nom enclature . Chemical S tructure

Common Name Acetamiprid Molecular Formula C 10 H 11 ClN 4 Molecular Weight 222.68 Company Experimental Name EXP - 61842A, AEF124370, NI - 25 IUPAC Name (E) -N 1

- [(6 - chloro - 3 - pyridyl)methyl] -N 2

- cyano -N 1

- methylacetamidine CA S Name (1 E) -N - [(6 - chloro - 3 - pyridinyl)methyl] -N' - cyano -N - methylethanimidamide CAS Registry Number 135410 - 20 - 7 End - use Product s (EP s ) Assail® 30SG (30% SG ; EPA Reg . No. 8033 - 36) Assail® 70WP (70% WP; EPA Reg . No. 8 033 - 23) Tristar® 30 SG (30% SG ; EPA Reg . No. 8033 - 94) Chemical S tructure of A cetamiprid M etabolite IM - 2 - 1

N 1

- [(6 - chloro - 3 - pyridyl)methyl] -N 2

- cyano - acetamidine Chemical S tructure of A cetamiprid M etabolite IM - 2 - 1 - amide ( also referred to as IM - 2 - 2)

N 2

- aminocarbonyl -N 1

- [(6 - chloro - 3 - pyridyl)methyl]acetamidine T able 2 . Physicochemical Properties of Technical - Grade Acetamiprid. Param eter Value Reference Melting Point/R ange (  C) 98.9 DP# 328216, W. Drew , 10/23/2007 pH 6.08 (Aqueous solution at 20  C) Density (g/cm3 ) 1.33 (at 20  C) Water Solubility (g/L) 4.25 (at 25  C) Solvent Solubility (at 25  C) Acetone >20 g/100 g Methanol >20 g/100 g Ethanol >20 g/100 g Dichloro methane >20 g/100 g Chloroform >20 g/100 g Acetonitrile >20 g/100 g Tetrahydrofuran >20 g/100 g Benzene 2.44 g/100 g Xylene 4.01 g/100 g n - Hexane 6.54 ppm Carbon disulfide 507 ppm

N N

C H 3 Cl C H 3 N C N

N N

H Cl C H 3 N C N

N N

H Cl C H 3 N O N H 2Acetamiprid Summary of Analytical Chemistry and Residue Data DP#: 364833

Page 9 of 38 T able 2 . Physicochemical Properties of Technical - Grade Acetamiprid. Param eter Value Reference Vapor Pressure (mm Hg) 7.5 x 10 - 9 (at 25  C) D P# 264154, M . Doherty; 12/31/2001 Dissociation Constant, pK a 0.7 (at 25  C) DP# 328216, W. Drew , 10/23/2007 Octanol/Water Partition Coefficient, Log KOW 0.8 (at 25  C) UV/Visible Absorption Spectrum Not available 860.1200 Directions for Use A list of acetamiprid end - use product s (EPs) relevant to this registration action is presented below in Table 3. All listed EPs are registered to Nippon Soda Co., Ltd. (c/o Nisso America, In c.). Table 3. List of Acetamiprid E nd - Use Products Associated with PP# 9E7544 . Trade Name Reg. No. ai (% of formulation) Formulation Type Label Date Assail® 30SG Insecticide 8033 - 36 30% by wt Soluble granule 3/4/20 09 (draft) Assail® 70WP Insecticide 8033 - 23 70% by wt Wettable powder 3/4/20 09 (draft) Tristar® 30SG Insecticide 8033 - 94 30% by wt Sol uble granule 3/4/20 09 (draft) A summary

of the proposed or amended use patterns is presented in Table 4. For clover, new use is proposed for Assail® 30SG and Assail® 70WP . For grapes, a change to the registered use pattern is proposed. The current lab el s permit up to two foliar applications on grapes at 0.05 lb ai/A/application for a maximum seasonal rate of 0.1 lb ai/A with a 7 - day preharvest interval (PHI ). The requested new use on grapes (and small vine climbing fruits, except kiwifruit, subgroup 1 3 - 07F ) will permit up to two applications of Assail® 30 SG or Assail® 70WP at 0.1 lb ai/A/application for a seasonal rate of 0.2 lb ai/A with a 3 - day PHI . For tomatoes , new use is proposed for greenhouse - grown tomatoes. The current Assail® 30 SG and Assail ® 70WP label s permit up to four foliar applications on field - grown tomatoes at 0.075 lb ai/A/application for a maximum seasonal rate of 0.3 lb ai/A with a 7 - day PHI . The requested new use on tomatoes will add a greenhouse use pattern for Tristar® 30 SG , wi th a maximum of two applications (reduced from four for resistance management) at 0.075 lb ai/A/application (based on 10,000 plants per acre) for a maximum seasonal rate of 0.15 lb ai/A, applied via chemigation with a 1 - day PHI . There were no rotational c rop restrictions listed on any of the acetamiprid draft labels. Table 4 . Summary of Directions for Use of Acetamiprid . Applic. Timing, Ty pe, and Equip. Trade Name

[EPA Reg. N o.] Applic.

Rate (lb ai/A) Max. No.

Applic. per Season 1 Max. Seasonal

Applic . Rate (lb ai/A) PHI

(days) Use Directions and

Limitations Clover 2 Postemergence Broadcast foliar spray Ground/aerial Assail®

30SG; [8033 - 36] Assail® 70WP [8033 - 23] 0. 047 -

0.075 1 0.075 28 Proposed use is limited to clover grow

n in ID, OR, and WA onl y. Begin applications w

hen treatment thresholds have been reached. Apply in minimum spray volumes of 5 GPA by air or 20 GPA by ground.Acetamiprid Summary of Analytical Chemistry and Residue Data DP#: 364833

Page 10 of 38 Table 4 . Summary of Directions for Use of Acetamiprid . Applic. Timing, Ty pe, and Equip. Trade Name

[EPA Reg. N o.] Applic.

Rate (lb ai/A) Max. No.

Applic. per Season 1 Max. Seasonal

Applic . Rate (lb ai/A) PHI

(days) Use Directions and

Limitations Grapes and Other Climbing Vine Small Fruits (Except Fuzzy Kiwifruit) (Within Crop Subgroup 13 - 07F ) : Am ur River Grape; Gooseberry; Hardy Kiwifruit; Maypop; Schisandra B erry; and Cultivars , Varieties, and/or H ybrids

Postemergence Broadcast foliar spray Ground/aerial Assail®

30SG; [8033 - 36] Assail® 70WP [8033 - 23] 0.047 - 0.1 2 0.2 3 Begin applications w hen treatment thres holds have been reached. Do not apply more than once every 14 days. Apply in minimum spray volumes of 5 GPA by air or 20 GPA by ground. Assail® 30SG states that the addition of a spreader, methylated seed oil or crop oil will enhance pest control . Gr eenhouse - Grow

n Tomatoes

Postemergence Drip or micro i rrigation Tristar®

30SG [8033 - 94] 0.075 lb

ai/A of crop ( based on 10,000 plants /A) 2 0. 15 1 For use in greenhouse grow n tomato production. May be applied by injection into drip irrigation or micro irrigation (spaghetti tube or emitter) systems, soil drenching, or by hand held or motorized calibrated irrigation equipment directed to the plant roots. Application should be made only to mature tomato plants grow n in non - soil media such as rock wool, vermi culite, perlite, or other soil - less media. S om e cultivars may exhibit sensitivity and therefore treatment of a few plants is recommended prior to treating an entire greenhouse. Begin applications w

hen treatment thresholds have been reached. 1 The numb er of treatments allowed per season when the EP is applied at the maximum single application rate. 2 Section G of the petition specifies that the EP is proposed for use on red clover grow n for seed. The draft label does not specify that use is for clo ver grow n for seed. TEA No use directions were proposed for the domestic use of acetamiprid on tea grown in SouthAcetamiprid Summary of Analytical Chemistry and Residue Data DP#: 364833

Page 11 of 38 Carolin a . The following GAP information was provided for the 20% SP formulation in Japan: one application at 0.10 - 0.40 kg ai/ha applied in 2000 - 4000 L/ha, with a 14 - day PHI . GAP information was also provided for India: one application at 0.022 lb ai/A (0.025 kg ai/ha) or 0.045 lb ai/A (0.050 kg ai/ha), shoots along with bud are ty pically harvested at a 7 - day

PHI . Conclusions . The submitte d labels are adequate to allow evaluation of the residue data relative to the proposed use , except for the use on tea in South Carolin a for which directions were not proposed . The available field trial data reflect the proposed use patterns for all of the submitted field trials except those submitted for grapes and clover hay . Because the grape field trial data submitted with this petition did not reflect the use of a surfactant in the application spray s, the label directions regarding use of a spreader, methylated seed oil or crop oil should be removed from the product label of Assail® 30SG (EPA Reg. No. 8033 - 36). The PHIfor clover harvested for hay should be increased to 56 day s on the 30SG and 70 WP labels. 860.1300 Nature of the Residue - Plants R esidue Chemistry Memo DP# 264154, 12 /31/2001, M . Doherty (PP#0F6082) MARC Decision Memo, DP# 278652, 11/13/2001, M. Doherty Plant metabolism studies with acetamiprid on apple, cabbage, carrot, cotton, and eggplant were submitted as p art of the data package for the original acetamiprid petition (PP#0F6082 ) , which adequately

delineate the qualitative nature of the residue in plants. It was found that in most plants, acetamiprid is demethylated at the N 1 amine to form IM - 2 - 1 , which may then be further metabolized to form IM - 0 and I C - 0. IM - 0 is then metabolized to form the glucose conjugate IM 0 - Glc. The HED has previously determined that the residue of concern in plants is acetamiprid for both tolerance e nforcement and risk assessment purposes. 860.1300 Nature of the Residue - Livestock Residue Chemistry Memo DP# 264154, 12 /31/2001, M . Doherty (PP#0F6082) MARC Decision Memo, DP# 278652, 11/13/2001, M. Doherty The qualitative nature of acetamiprid residues in liv es tock is adequately understood. HED has previously determined that the tolerance expression for enforcement purposes in livestock commodities should be acetamiprid plus its IM - 2 - 1 metabolite. For the purpose of risk assessment, the residues of concern i n livestock commodities (except ruminant muscle) are acetamiprid plus its IM - 2 - 1 metabolite. In ruminant muscle, the residues of concern for risk assessment are acetamiprid plus IM - 2 - 1 plus IM - 2 - 1 - amide. These conclusions are based on acceptable metaboli sm studies with lactating goats (1 ppm or 8.6 ppm dosing levels administered for 7 day s) and laying hens (1.1 ppm or 12.5 ppm dosing levels administered for 14 days ) . Metabolism data indicate that levels of IM - 2 - 1 - amide will not exceed 10x the level of IM - 2 - 1 in ruminant muscle tissue. Acetamiprid is metabolized in goats via loss of an amine methy l group, forming IM - 2 - 1, which can further hydroly zed to form IM - 2 - 3 and IM - 2 - 4. IM - 2 - 2 can be formed as an intermediate in the metabolism of IM - 2 - 1 to IM - 2 - 4. Inpoultry , IM - 2 - 2 can be converted to IM - 2 - 5 through loss of the acetamide group. 860.1340 Residue Analytical Methods Residue Chemistry Memo DP# s 342549 & 355773 , 1 1 / 05 /200 8 , W. DrewAcetamiprid Summary of Analytical Chemistry and Residue Data DP#: 364833

Page 12 of 38 Residue Chemistry Memo DP # 328216 , 1 0 /2 3/200 7 , W. Drew (PP#6F7051 and PP#6E7163) Residue Chemistry Memo DP# 303623, 11/05/2004, W. Drew (PP#4F6833) Residue Chemistry Memo DP# 264154, 1 2 /31/2001, M . Doherty (PP#0F6082) Enforcement m ethod s : Adequate residue analy tical methods (GC/ECD and HPL C/UV) are available for the enforcement of established tolerances on plant commodities. The method L OQs are 0.010 ppm for vegetables and non - citrus fruits (GC/ECD), and 0.050 ppm for citrus fruits (HPL C/UV). These methods have undergone successful petition method validation ( PMV ) trials. Under PP#4F6833, Nisso America proposed that the L C/MS/MS method utilized for data collection and confirmatory analy sis (Method #KP - 216R0 or it s modification, Method #KP 216R1) be designated an alternative to the established GC/ECD tolerance enforcement method. With submission of acceptable independent laboratory validation ( ILV ) data and the ability to analy ze two daughter ions specific to acet amiprid , the LC /MS/MS method, was determined to be suitable for tolerance enforcement and confirmatory analy sis of vegetables and non - citrus fruits (DP# s 342549 & 355773 ) . A summary of the available methods is presented in Table 5. Table 5. Summary of V alidated Analytical Methods for Acetamiprid. Target Matrices Method Description LOQ (ppm) Method Validation

Fortification Levels (ppm) Recovery

Range (%) Vegetables and Non - Citrus Fruits Methanol extraction, residues partitioned into

dichloromethane, Florisil/silica gel column cleanup, and L C/MS/MS determination. 0.010 0.010, 0.0 2 0 72 - 80 Vegetables and Non - Citrus Fruits Methanol extraction, residues partitioned into

dichloromethane, Florisil/silica gel column cleanup, and GC/ECD determination. 0.010 0.010, 0.050 68 - 112 Citrus Fruits Acetonitrile extraction, co - extractives partitioned

into hexane, residues partitioned into dichloromethane, Florisil/C18 column cleanup, and HPLC/UV determination. 0.050 0.050, 0.250 77 - 100

Data - collection methods: Samples from the clover and grape field trials submitted in conjunction with the subject petition were analy zed for residues of acetamiprid using L C/MS/MS Method #KP - 216R1 or a modification of Method #KP - 216R1. Samples from the tomato field trials were analy

zed for residues of acetamiprid using a GC/ECD working method entitled “Residue Analy sis of Acetamiprid on Tomato (greenhouse) by GC/EC Detection”, adapted with modifications from the reference method, “Methods for the Analysis of Acetamiprid (NI - 25) in Pl ants and Plant Process Fractions . ” A cceptable recoveries were obtained in method validation conducted prior to the analy sis of field trial samples and/or concurrent method validation using clover forage, clover hay , grapes, and tomatoes fortified with ace tamiprid at levels ranging from the lowest limit of method validation (LLM V; 0.010 ppm) and up to 1. 0 0 ppm. The fortification levels used in method validation and concurrent method validation were adequate to bracket the expected residue levels for all trials . Tea: Inthe Japan study , samples of dried green tea leaves and brewed tea were analy zed for combined residues of acetamiprid and metabolites convertible to 6 - chloronicotinic acid (Metabolite I C - 0) using a common moiety GC/ECD method. Briefly , drie d tea leaves were homogenized, soaked in water, and then extracted with methanol. Brewed tea was simply filtered. The resulting extracts/filtrates were partitioned with hexane, and the aqueous layer wasAcetamiprid Summary of Analytical Chemistry and Residue Data DP#: 364833

Page 13 of 38 subjected to base hydroly sis. Acetamiprid and meta bolites were then converted to 6 - chloronicotinic acid by

oxidation, then methylated (procedure not specified) and purified by silica column chromatography prior to GC/ECD analy sis. The reported method L OD was 0.05 ppm as acetamiprid. Inthe India study samples of green shoots, dried black tea leaves, brewed tea, and spent leaves were analy

zed for residues of acetamiprid using an HPL C/UV method. Briefly , green shoots, and dried and spent leaves were extracted with acetonitrile, then filtered. The filtrate was concentrated and transferred to a separatory funnel containing petroleum ether:5% NaCl solution (5:5, v:v). Following shaking and phase separation, the organic phase was washed twice with NaCl solution, and the aqueous phases were combined and par titioned with dichloromethane (DCM; 4x). The resulting extracts were concentrated to dry ness, reconstituted in acetone:hexane (5:5, v:v), and purified by silica - carbon column chromatography ; residues were eluted with acetone/hexane prior to HPL C/UV analy s is. Samples of brewed tea were extracted with DCM (4x), and the organic layers were combined and concentrated for analysis by HPL C/UV. The reported LOD was 0.05 ppm. O nly limited details were provided for the analy tical phase for both studies and that no raw data were included for either study . Conclusions : Adequate residue analy tical methods (GC/ECD, HLPC/UV and L C/MS/MS) are available for the purpose of tolerance enforcement. The GC/ECD and LC /MS/MS Method s used for the anal ys is of samples from the clover, grape, and tomato field trials are similar to the enforcement methods, and were adequate as data - collection methods based on a cceptable method validation recoveries from clover forage, clover hay , grapes, tomatoes , and tea . 860.1360 Multiresidue Methods Residue Chemistry Memo DP# 264154, 1 2 /31/2001, M . Doherty (PP#0F6082) The petitioner submitted data concerning the recovery of residues of acetamiprid using FDA multiresidue method protocols (PAM Volume I ) in conjunction with the original acetamiprid petition ( PP#0F6082 ). These data have been forwarded to FDA for evaluation. Based on the results of the testing, the multiresidue methods are not appropriate for determining acetamiprid residues of conce rn . The Biological and Economic Analysis Division ( BEAD ) is currently working on a multi - residue method for the neonic o tinoids. 860.1380 Storage Stability Residue Chemistry Memo DP# 303623, 11/05/2004, W. Drew (PP#4F6833) Residue Chemistry Memo DP# 264154, 1 2 /31/2001, M . Doherty (PP#0F6082) Storage stability

data submitted with PP#6F7051 indicate that residues of acetamiprid are relatively stable under frozen storage conditions for up to 12 months in/on fortified samples of an oils eed (cotton seed), a leafy vegetable (head lettuce), a Brassica leafy vegetable (cabbage), a cucurbit vegetable (cucumber), and fruits (apple and orange), as well as the processed commodities of apple, cotton, and orange. In addition, the stability of ace tamiprid during short term storage at ambient temperatures was evaluated. Samples of cottonseed, cotton ginAcetamiprid Summary of Analytical Chemistry and Residue Data DP#: 364833

Page 14 of 38 by products , cotton seed oil, whole grapes, grape juice, raisins, whole oranges, whole tomatoes, and tomato paste spiked with acetamiprid at 0.10 0 and 0.25 0 ppm were stored at ambient temperatures for 7 day s (15 day s for raisins). Under these conditions, residues of acetamiprid were stable in all commodities. IR - 4 conducted concurrent storage stability stud ies with the analy sis of the field trial samples in conjunction with the clover and tomato field trials. Although no 0 - day data were provided, the data indicate that residues of acetamiprid are relatively stable under frozen storage conditions in/on fortified samples of clover forage for up to 2 39 day s (7.9 months), clover hay for up to 213 day s (7.0 months), and tomatoes for up to 114 day s (3.7 months). The storage durations and conditions of samples from the submitted crop field trials are presented below in Table 6 . Table 6 . Summary of S torage Conditions and Duration s of Samples fromCrop Field Trial Studies . Matrix Storage Temperature

(°C) Actual Storage Duration Interval of Demonstrated Storage Stability Clover forage - 29 to - 10 224 - 227 days (7.4 - 7.5 months) Up to 239 days in/on fr ozen clover forage. Clover hay 195 - 204 days (6.4 - 6.7 months) Up to 213 days in/on frozen clover. Grape - 28 to - 10 49 - 125 days (1.6 - 4.1 months) Up to 12 months in/on diverse representative crops, including fruits . Tomato - 21 ± 7 20 - 99 days (0.7 - 3.3 months) Up to 114 days in/on frozen tomato . Conclusions . The available storage stability data for acetamiprid on representative crops , and the submitted concurrent storage stability data for clover and tomato are adequate to support the submitted clover, gr ape, tomato , and tea field trials. There is no need for correction of residues , as no decline in residue was observed. 860.1480 Meat, Milk, Poultry, and Eggs The proposed use on clover could theoretically lead to the secondary transfer of acetamiprid r esidues of concern to beef and dairy cattle from the feeding of clover forage, hay , and silage. However, the proposed use on clover is to be restricted to th at grown in ID, OR, and WA only . Therefore, HED does not believe that the proposed use on clover would significantly increase the dietary burdens, and the established tolerances in milk, meat, and meat by products need not be reassessed for the purpose of this petition. 860.1500 Crop Field Trial sAcetamiprid Summary of Analytical Chemistry and Residue Data DP#: 364833

Page 15 of 38 DER Reference List 47716901.der.doc (Clover) 477169 02.der.doc (Grapes) 47716903.der.doc (Greenhouse Tomatoes) 47782101.der.doc (Tea) Residue Chemistry Memo DP# 264154, 1 2 /31/2001, M . Doherty (PP#0F6082) Minutes of the 11/16/2005 Meeting of the HED Chemistry SAC IR - 4 has submitt ed magnitude of the residue data for acetamiprid on red clover, grapes, and tomato , and tea to support the new uses on clover and greenhouse tomatoes, tea and amended use on grapes (also expanded to small vine climbing fruits, except fuzzy kiwifruit, subgr oup 13 - 07F). A summary

of the residue data is presented in Table 7 a and 7b .

Table 7 a . Summary of Residue Data fromCrop Field Trials with Acetamiprid . Crop M atrix Total Applic. Rate (lb ai/A) PHI

(days) Residue Levels (ppm)

n Min. Max. HAFT 1 M edian Mean Std. Dev. Clover ( P roposed use = One broadcast foliar spray treatm ent at a m axim um of 0.075 lb ai/A; 28 - day PHI ) Clover forage 0.074 - 0.079 28 - 34 6 <0.01 0.05 0.05 0.05 0.04 0.02 Clover hay 56 - 63 6 <0.01 <0.01 <0.01 0.01 0.01 -- Grapes and O ther Climbing Vine Sm all Fruits (Except Fuzzy Kiwifruit) (Within Crop Subgroup 13 - 07F)

( Current registered use on Grapes = 0.1 lb ai/A total application rate; 7 - day PHI) (Proposed am ended use = 0.2 lb ai/A total application rate; 3 - day PHI) Grape 0.195 - 0. 206 2 - 3 36 0.01 0.25 0.25 0.08 0.11 0.07 Tom atoes (Current registered field use = 0.3 lb ai/A total application rate; 7 - day PHI) (Proposed greenhouse use = 0.15 lb ai/A total application rate; 1 - day PHI) Tomato 0.300 - 0.324 1 6 <0.01 0.052 0.050 0.027 0.0 29 0.018 1 HAFT = Highest average field trial result. TABLE 7b. Summary of Residue Data from Crop Field Trials with Acetamiprid. Commodity Total Applic. Rate, lb ai/A [kg ai/ha] PHI

(days) Residue L evels (ppm)

n Min. Max. HAFT 1 Median (STMdR) Mean

(STMR) Std. Dev. Japan Study - Combined residues of acetamiprid and residues convertible to Metabolite IC - 0 Green tea - dried leaves 0.13 - 0.27

[0.15 - 0.30] 6 - 7 8 13.6 40.9 39.3 23.9 25.3 9.82

13 - 14 8 8.15 17.2 16.6 13.1 12.8 4.19 20 - 21 8 2.30 5.44 5.44 3.64 3.75 1.19 Green tea - brewed tea * 0.13 - 0.27

[0.15 - 0.30 6 - 7 8 7.74 27.7 27.0 17.3 17.4 7.29

13 - 14 8 5.17 12.7 12.6 9.21 9.07 3.38 20 - 21 8 1.57 3.30 3.27 1.87 2.15 0.70 India Study (wet and dry season tea) - Residues of acetamiprid per se (only mean values reported) 2 Black tea - green shoots 0.022 - 0.045

[0.025 - 0.050] 0 12 3.96 9.53 9.53 NC 3 6.54 NC

7 12 0.20 0.51 0.51 NC 0.33 NC 15 12 0.03 0.11 0.11 NC 0.06 NC 21 12 <0.05 <0.05 < 0.05 < 0.05 < 0.05 0 Black tea - dried leaves 0.022 - 0 .045

[0.025 - 0.050] 0 12 11.2 26.4 26.4 NC 18.5 NC

7 12 0.54 1.47 1.47 NC 0.95 NC 15 12 <0.05 0.26 0.26 NC 0.11 NC 21 12 <0.05 <0.05 < 0.05 < 0.05 < 0.05 0 Black tea - 0.022 - 0.045 0 12 5.4 12.6 12.6 NC 8.92 NCAcetamiprid Summary of Analytical Chemistry and Residue Data DP#: 364833

Page 16 of 38 TABLE 7b. Summary of Residue Data from Crop Field Trials with Acetamiprid. Commodity Total Applic. Rate, lb ai/A [kg ai/ha] PHI

(days) Residue L evels (ppm)

n Min. Max. HAFT 1 Median (STMdR) Mean

(STMR) Std. Dev. brewed tea * [0.025 - 0.050] 7 12 0.24 0 .61 0.61 NC 0.41 NC 15 12 <0.05 0.13 0.13 NC 0.07 NC 21 12 <0.05 <0.05 < 0.05 < 0.05 < 0.05 0 Black tea - spent leaves 0.022 - 0.045

[0.025 - 0.050] 0 12 4.6 10.2 10.2 NC 7.5 NC

7 12 0.20 0.51 0.51 NC 0.36 NC 15 12 <0.05 0.09 0.09 NC 0.06 NC 21 12 <0.05 <0.05 < 0.05 < 0.05 < 0.05 0 1 HAFT = Highest Average Field Trial. 2 The reported LOD (0.05 ppm) was used for calculation of median, mean, and standard deviation where appropriate. Only the 0 - day PHI and PHIs relevant for comparison to the Japan tria ls were included in the summary. 3 NC = Not calculated. Median and standard deviation could not be calculated because only mean values were reported for each sample set. 4 NA = Not applicable when all residues are nonquantifiable (<0.05 ppm). * The relatively high residues in the brewed tea, which HED expected to be much lower than the residues in or on the dried tea leaves, may reflect a back calculation of what the residues would have been on the dried tea leaves. Otherwise, HED can not account fo r why the residues were not diluted by the water used for making the tea. Clover Three red clover field trials were conducted in the U.S. in Zone 11 (OR) during the 2006 growing season. Each trial site consisted of one untreated plot and one treated plo t. Red clover was treated with a single broadcast foliar application of Assail® 30SG, a 30% SG formulation of acetamiprid, at a rate of 0.074 - 0.079 lb ai/A ( ca. 1x the maximum proposed seasonal rate on clover). Application was made when the crop was in the vegetative stage to blooming stage using ground equipment in 23 - 25 GPA spray volumes, without an adjuvant. Samples of clover forage were harvested 28 to 34 day s following application. Additionally , hay samples were cut at a normal harvest time (coinci ding with PHI s of 56 - 63 day s) and allowed to dry in the field prior to collection. Samples were analy

zed for residues of acetamiprid using an L C/MS/MS working outline based on Cerexagri Method No. KP - 216R1. The adequacy of the method for data collection was verified by

analy sis of untreated samples of red clover forage and hay fortified with acetamiprid at 0.01 - 1.0 ppm. Overall method recoveries ranged 75% to 96% for forage, and 75% to 100% for hay . The fortification levels used in method validation ade quately bracketed the expected residues in/on treated clover forage and hay . The validated LOQ ( and LLM V) was 0.01 ppm in both clover forage and hay . Samples were held in frozen storage prior to analysis. The maximum sample storage durations, from harve st to analy sis, were 227 day s (7.5 months) for clover forage, and 204 days (6.7 months) for clover hay . Sample storage conditions and durations are supported by concurrent storage stability

data. The results of the clover field trials are summarized in Table 7. R esidues of acetamiprid were <0.01 - 0.05 ppm in/on red clover forage harvested 28 - 34 day s following a single broadcast foliar application of the 30% SG at 0.074 - 0.079 lb ai/A. Residues were below the LLM V (<0.01 ppm) in/on clover hay

harvested 5 6 - 63 day s following treatment. Conclusions : The use pattern of the clover field trials adequately reflects the proposed label use pattern with the exception of the PHIfor hay . The available field trial data indicate a regionalAcetamiprid Summary of Analytical Chemistry and Residue Data DP#: 364833

Page 17 of 38 tolerances for residues o f acetamiprid in clover forage at 0.10 ppm and clover hay at 0.01 ppm , are appropriate . However, the submitted clover field trial data are not completely adequate to satisfy data requirements. The three clover field trials were all conducted in Zone 11 ( OR) during the 2006 growing season, at the same location and within a very short time period of each other. The number of trials are adequate to support restricted use on clover in ID, OR and WA (Zones 11 and 12) according to OPPTS Guideline 860.1500, Att achment 11; however the guidelines state that for crops requiring 8 or more trials nationally (12 are required for clover), the trials for regional registrations must be conducted in multiple years to account for variability due to climate conditions. As a condition of registration, HED recommends that two additional clover field trials be required, as confirmatory data. Inaddition, the submitted reside data included field trial data for only the 70WP formulation (the original field trials also used a 70 WP formulation). However, since the requested PHI is for 28 day s, additional residue chemistry field trial data are not required to support registration of the 30SG formulation (generally bridging data are required if the proposed PHI is less than or equa l to 7 day s) . U se on clover grown for seed is to be limited to clover grown in ID, OR, and WA. Since the residue chemistry data submitted for clover hay

reflect PHI s of between 56 - 63 day s, the PHIfor acetamiprid use on clover should be increased to 56 d ay s for any clover crop which will be harvest ed for hay . No residue decline data were included in the clover field trials. However, r esidue decline studies on cotton, head lettuce, oranges, pears, and peppers were submitted in conjunction with PP#0F6082 ( D 264154 , 12/31/2001, M. Doherty ). These data indicated that residues of acetamiprid did not increase in the subject crops with increasing harvest intervals. Given the long PHI(28 - day s) for clover and available residue decline data on other crops, resid ue decline data will not be required to support the clover field trials. The available field trial data will support tolerances with regional registration for residues of acetamiprid in clover forage at 0.10 ppm (with a 28 - day

PHI ) and clover hay

at 0.01 ppm (with a 56 - day PHI ) ; the tolerance calculation s for clover forage are presented in Appendix I . Grape; Fruit, Small Vine Climbing, Subgroup 13 - 07F, Except Fuzzy Kiwifruit Eighteen grape field trials were conducted in the U.S. and Canada in Zones 1 (NY; 1 trial), 2 (NJ; 2 trials), 5 (ON; 4 trials), 5A (MI ; 1 trial), 10 (CA; 8 trials), 11 (BC; 1 trial), and 11/12 (WA; 1 trial) during the 2005 growing season. Mature grape vines in established orchards were treated with two directed foliar applications o f Assail® 70WP, a 70% WP formulation of acetamiprid, at 0.096 - 0.103 lb ai/A/application, with a 13 - to 14 - day retreatment interval (RTI ) , for a total rate of 0.195 - 0.206 lb ai/A ( ca. 1x the maximum proposed seasonal rate on grapes and other climbing vine s mall fruits). Applications were made during the crop’s fruiting to berry ripening stages using ground equipment in 22 - 130 GPA spray volumes, without an adjuvant. Samples of mature grape fruits were harvested 2 to 3 day s after the second application. Samples were analy

zed for residues of acetamiprid using an L C/MS/MS method based on Cerexagri Method No. KP - 216R1. The adequacy of the method for data collection was verified by analy sis of untreated samples of grapes fortified with acetamiprid at 0.01 - 1.0 p pm. Overall method recoveries ranged from 80% to 98%. The fortification levels used in method validation adequately

bracketed the expected residues in/on treated grapes. The validated LOQ ( and LLM V) was 0.01 ppm in grape. Samples were held in frozen st orage prior to analy sis. The maximum sample storage durationAcetamiprid Summary of Analytical Chemistry and Residue Data DP#: 364833

Page 18 of 38 from harvest to analy sis was 125 day s (4.1 months) for grape. Adequate storage stability data are available for acetamiprid demonstrating that residues are stable in/on diverse representative c rops (including fruits) for up to one year. The results of the grape field trials are summarized in Table 7. R esidues of acetamiprid were 0.01 - 0.25 ppm in/on grapes harvested 2 - 3 day s following the last of two directed foliar applications of the 70% WP at a total rate of 0.195 - 0.206 lb ai/A. No residue decline data were included in the grape field trial study . Conclusions : The submitted grape residue data included field trial data for only the 70WP formulation (the original field trials also used a 7 0WP formulation). Since the requested PHI for grape is for 3 day s, additional residue chemistry field trial data are needed to support registration of the 30SG formulation. As a condition of registration, HED requests that three side - by- side field trials be conducted and submitted to determine if residues are comparable for the two different formulations. The submitted grape field trial data are adequate for the 70 WP formulation pending label revision. Because the grape field trial data did not reflect the use of a surfactant in the application spray s, the label directions regarding use of a spreader, methylated seed oil or crop oil should be removed from the product label of Assail® 30SG (EPA Reg. No. 8033 - 36). The number and locations of the field trials are in accordance with OPPTS Guideline 860.1500 for grapes, and the use pattern of the field trials reflects the use pattern proposed for grapes ( and o ther c limbing v ine s mall f ruits , e xcept f

uzzy k iwifruit , within s ubgroup 13 - 07F) , except for the ad juvant use. No residue decline data were included in the grape field trials. The r esidue decline studies from PP#0F6082 ( DP# 264154 , 12/31/2001, M. Doherty ) , which indicated that residues of acetamiprid did not increase in various crops with increasing harvest intervals , will be used to fulfill the requirements for residue decline data . The available field trial data from the current submission, which reflect a higher seasonal rate and a shortened PHI from th ose which are currently registered for grape , will support a tolerance for residues of acetamiprid at 0.35 ppm ; the tolerance calculation s for grape are presented in Appendix I . Grape is the representative crop of the fruit, small vine climbing, subgroup 13 - 07F, except f uzzy k iwifruit , and the av ailable grape data will support a subgroup tolerance at 0.35 ppm. The established individual tolerance for grape at 0.20 ppm should be deleted when the s ubgroup 13 - 07F tolerance is established . Tomatoes (Greenhouse Study ) Three trials were conducted on tomatoes in the U.S. and Canada in Zones 4 (TN), 5 (ON), and 6 (TX) during the 2002 and 2003 growing seasons. Each trial site included one untreated plot and one treated plot. Tomato plants grown in rock wool substrate under greenhouse conditions were tr eated at the fruiting stage with four simulated drip - irrigation (chemig ation) treatments of Assail® 70 WP, a 70% WP formulation of acetamiprid, at rates equivalent to 0.074 - 0.081 lb ai/A/application. Applications were made with 7 - day RTI s , for a total rate of 0.300 - 0.324 lb ai/A ( ca. 2x the maximum proposed seasonal rate for greenhouse - grown tomato); no adjuvant was used. Samples of mature tomato were harvested one day after the last application. At the TXAcetamiprid Summary of Analytical Chemistry and Residue Data DP#: 364833

Page 19 of 38 trial, additional treated samples were harvested 3, 5, and 7 day s after the last application to generate residue decline data. Samples were analy

zed for residues of acetamiprid using a GC/ECD working method entitled “Residue Analy sis of Acetamiprid on Tomato (greenhouse) by GC/EC Detection”, adapted with modifications from the reference method, “Methods for the Analysis of Acetamiprid (NI - 25) in Plants and Plant Process Fractions.” The adequacy of the method for data collection was verified by analy sis of untreated samples of tomato fruit fortified with acetamiprid at 0.01 - 1.0 ppm. Overall method recoveries ranged from 86% to 120%. The fortification levels used in method validation adequately

bracketed the expected residues in/on treated tomato. The validated LOQ ( and LLM V) was 0.01 ppm in tomato. To mato samples were held under frozen storage condition s for a maximum duration of 99 days (3.3 months) prior to residue analysis. Sample storage conditions and durations are supported by concurrent storage stability data. The results of the greenhouse grown tomato field trials are summarized in Table 7. R esidues of acetamiprid ranged from below the LLMV (<0.01 ppm) to 0.052 ppm in/on greenhouse - grown tomatoes harvested one day following the last of four drip - irrigation (chemigation) treatments of the 70 % WP at a total rate of 0.300 - 0.324 lb ai/A. The decline data show that residues accumulated slightly , from an average of 0.027 ppm at the 1 - day PHIto an average of 0.037 ppm at the 7 - day

PHI . Conclusions: The submitted tomato data do not reflect the p roposed greenhouse use pattern because the application rate used in the trials is 2x the proposed seasonal rate for tomatoes grown under greenhouse conditions. Inaddition, the three trials conducted are marginally adequate with respect to the number of trials. Because the established field tomato uses differ from the proposed greenhouse - grown tomato use, HED (ChemSAC 11/16/05 minutes) ty pically re quires data depicting residues from 4 greenhouse sites, with 4 samples per site . For chemicals with tomato t olerances resulting from a field use and for which the field and greenhouse use patterns are similar, any

of the following 3 study

designs w ould generally

be found to be appropriate: (i) residue data from 3 greenhouse sites with 2 samples per site; (ii) residue decline data, encompassing the proposed PHI , from 2 greenhouse sites with 2 samples per time interval; or (iii) residue data from 2 greenhouse sites with 4 samples per site. Although the greenhouse trials were conducted at a 2x rate and the number of trials is marginal, no additional residue data will be required to support the proposed greenhouse use pattern for tomatoes if use is limited to the WP formulation . T he tomato greenhouse data indicate that resulting acetamiprid residues resulting from applications of Assail 70WP formulation of acetamiprid according to the proposed use pattern would not exceed the established tolerance for residues of acetamiprid in fruiting vegetables , c rop group 8 ( 0.20 ppm ). No data were provided for the proposed use of Tristar® 30SG on greenhouse tomatoes. HED does have side - by- side formulation trials (WP and soluble liquid formulation) for acetamiprid in undelinted cottonseed and cotton gin by

products (D330540, M. Doherty , 30 Oct 2007) . These data indicate that re sidue level s are comparable for the two different formulation s at the same use rate . In view of these data and the 70WP data reflecting 2x the seasonal application rate , HED requests on ly one side by- side formulation trial (rather than the normal of three trials) to support the use of Tristar® 30SG on greenhouse tomatoes as a condition of registration .Acetamiprid Summary of Analytical Chemistry and Residue Data DP#: 364833

Page 20 of 38 Tea The Interregional Research Project No. 4 (IR - 4) has submitted a report summarizing the results of two studies on tea conducted in Japan (by Nippon So da Co., Ltd.) and India (by the Institute of Himalayan Bioresource Technology ; IHBT). No raw data were included in the submission, all data presented herein are as reported in the original studies. Nippon Soda Co, Ltd. conducted two trials in the Mie Pre fecture and the Fukuoka Prefecture of Japan investigating the magnitude of the residue in dried green tea leaves and brewed tea following a single foliar application of a 20% w ater - soluble powder (SP) formulation of acetamiprid made to green tea in separat e plots at 0.13 lb ai/A (0.15 kg ai/ha) and 0.27 lb ai/A (0.30 kg ai/ha). Applications were made in spray volumes of 321 gal/A (3000 L/ha). The following Good Agricultural Practice (GAP) information was provided for the 20% SP formulation in Japan: one foliar application at 0.10 - 0.40 kg ai/ha applied in 2000 - 4000 L/ha, with a 14 - day

preharvest interval (PHI). Duplicate samples of green tea leaves were harvested 6 - 7, 13 - 14, and 20 - 21 day s after application, and were processed into dried leaves and brewed tea (green tea drink) according to standard procedures for green tea. Ina separate study , the Institute of Himalayan Bioresource Technology (IHBT) conducted two sets of trials in Palampur (Himachal Pradesh, India) investigating the magnitude of the re sidue in black tea for green shoots, dried tea leaves, brewed tea, and spent leaves after brewing. Acetamiprid was applied to black tea in separate plots as a single foliar application of a 20% SP formulation of acetamiprid at 0.022 lb ai/A (0.025 kg ai/h a) and 0.045 lb ai/A (0.050 kg ai/ha) in spray volumes of 43 gal/A (400 L/ha). The application rates were reported to be 1x and 2x the recommended application rate for acetamiprid on tea. Two sets of trials were conducted, one during the dry

season (June ) and the second during the wet season (August). The following GAP information was provided for India: shoots along with bud are ty pically harvested at a 7 - day PHI . Samples of green shoots (consisting of two leaves and a bud) were collected 0 (2 hours p ost application), 1, 3, 5, 7, 9, 11, 15, and 21 days after application; three replicate samples were collected from each plot at each sampling interval. Samples were processed into dried tea leaves and brewed tea (infusion) using standard procedures for b lack tea production; samples of spent leaves following brewing were also collected. Samples of dried green tea leaves and brewed tea from the Japan study were analy

zed for residues of acetamiprid and its metabolites convertible to 6 - chloronicotinic acid (Metabolite I C 0) using a common moiety gas chromatography

method with electron capture detection (GC/ECD) . Using this method, acetamiprid and metabolites are converted to Metabolite I C - 0 and methylated prior to determination by GC/ECD; residues are expre ssed as acetamiprid. The reported method limit of detection (L OD) is 0.05 ppm as acetamiprid. Samples of green shoots, dried black tea leaves, brewed tea, and spent leaves from the India study were analy

zed for residues of acetamiprid using a high perfor mance liquid chromatography method with ultraviolet detection (HPL C/UV). The reported LOD was 0.05 ppm. Both methods are adequate for data collection based on the submitted concurrent recovery data; however, we note that the fortification levels used in c oncurrent method validation in the Japan study did not encompass residues found in dried green tea leaves or brewed tea. Regarding the common moiety method used in the Japan study , we note that, althoughAcetamiprid Summary of Analytical Chemistry and Residue Data DP#: 364833

Page 21 of 38 Metabolite I C - 0 is not a residue of concern for to lerance enforcement or risk assessment, based on the available plant metabolism studies, it may constitute a significant portion of the total residues (e.g., up to 24% total radioactive residues (TRR) in cotton seed and 31% TRR in carrot flesh; refer to D2 78652, 11/13/01, H. Bietlot and M. Doherty ). Therefore, the residues reported for the Japan study

may reflect an overestimation of expected residues of acetamiprid per se in green tea. Samples of dried green tea leaves and brewed tea from the Japan study were stored frozen from collection to analy sis for up to 3.5 and 1.7 months, respectively . Storage conditions and durations for samples of green shoots, dried black tea leaves, brewed tea, and spent leaves from the India study

were not reported; however, the study indicated that samples were analy zed immediately

after receipt in the laboratory and that extensive storage was not required. HED believes there are sufficient storage stability data available for acetamiprid, demonstrating that residues are st able in crop commodities stored frozen for up to 12 months and crop commodities stored at ambient temperatures for up to 7 days, to support both studies (refer to D264154, 12/31/01, M. Doherty

). Following a single foliar application of the 20% SP formulat ion of acetamiprid at 0.13 - 0.27 lb ai/A (0.15 - 0.30 kg ai/ha) to green tea grown in Japan, combined residues of acetamiprid and metabolites were 13.6 - 40.9 ppm in dried green tea leaves harvested 6 - 7 day s after application and were 8.15 - 17.2 and 2.30 - 5.44 pp m in dried leaves harvested 13 - 14 and 20 - 21 day s after application, respectively . In brewed tea produced from the dried leaves harvested at the 6 - to 7 - , 13 - to 14 - , and 20 - to 21 - day PHI s, residues were 7.74 - 27.7, 5.17 - 12.7, and 1.57 - 3.30 ppm, respective ly . Following a single foliar application of the 20% SP formulation of acetamiprid at 0.022 - 0.045 lb ai/A (0.025 - 0.050 kg ai/ha) to black tea grown in India during the wet and dry seasons, combined residues of acetamiprid in green shoots harvested at 0 - , 7, - 15, and 21 - day PHI s were 3.96 - 9.53, 0.20 - 0.51, 0.03 - 0.11, and <0.05 ppm, respectively . Residues in dried black tea leaves processed from the shoots were generally higher at the 0 - , 7 - , and 15 - day PHI s, 11.2 - 26.4, 0.54 - 1.47, and <0.05 - 0.26 ppm, respect ively , and were <0.05 ppm at the 21 - day PHI . Residues were 5.4 - 12.6, 0.24 - 0.61, and <0.05 - 0.13 ppm, respectively , in brewed tea, and 4.6 - 10.2, 0.20 - 0.51, and <0.05 - 0.09 ppm, respectively , in spent leaves from tea harvested at the 0 - , 7 - , and 15 - day PHI s, and were <0.05 ppm in brewed tea and spent leaves at the 21 - day PHI . The study report also contained a list of multiresidue method analysis results for residues of acetamiprid in tea received in commercial shipments from various countries. Although resid ues were nondetectable in the majority of green and black tea samples received from Argentina, Bangladesh, Burundi, China, Ecuador, Ethiopia, India, Indonesia, Iran, Kenya, Malawi, Mozambique, Rwanda, Sri L anka, South Africa, Tanzania, Turkey , Uganda, Vietnam, Zimbabwe, detectable residues of acetamiprid were found in tea samples from China (0.03 - 0.04 ppm; n=3), Indonesia (0.03 ppm; n=1), and Vietnam (0.03 - 0.12 ppm; n=7). The source of these data was not identified.Acetamiprid Summary of Analytical Chemistry and Residue Data DP#: 364833

Page 22 of 38 860.1520 Processed Food and Feed Residue Chemistry Memo DP# 264154, 1 2 /31/2001, M . Doherty (PP#0F6082) No new processing studies were submitted with this petition request. Grape An a cceptable grape processing study (MRID 449886 20) was reviewed under PP# 0F6082 which reported processing factors of 1.5x for juice and 0.9x for raisins. Expected residues, based on the new HAFT (0.25 ppm) for grape from the amended use, would be 0.375 ppm in juice and 0.225 ppm in raisins. Based on these data, no tolerance i s needed in grape raisins as a result of the proposed use because any expected residues in raisins are less than the RAC tolerance. Considering that the maximum theoretical concentration factor for grape juice is 1.2 (Guideline 860.1520), HED also expect s residues in grape juice, resulting from the proposed use, will not exceed the RAC tolerance of 0.35 ppm; therefore, a separate tolerance is not needed for grape juice. Tomato An acceptable tomato processing study (MRID 44988621) was reviewed under PP# 0F6082 which reported processing factors of 1.4x for puree and 3.0x for paste. Based on the observed processing factor of 3.0x and a HAFT of 0.1 ppm, a tolerance of 0.40 ppm w as established for residues of acetamiprid in tomato paste. A tolerance wa s not needed in p uree because any expected residues in puree would be less than the RAC tolerance ( 0. 20 ppm) . The proposed use on greenhouse - grown tomatoes will not change the expected residues in puree or paste. 860.1650 Submittal of Analytical R eference Standards An analy tical standard for acetamiprid is currently available in the National Pesticide Standards Repository

(personal communication with Dallas Wright, ACB, 07/06/2009). However, analy tical standard s for the IM - 2 - 1 and IM - 2 - 1 - amide me tabolite s are not available at the Repository . Analy

tical reference standards of these metabolites must be supplied and supplies replenished as requested by the Repository . The reference standards should be sent to the Analy tical Chemistry

L ab, which is located at Fort Meade, to the attention of Theresa Cole at the following address: USEPA National Pesticide Standards Repository /Analy tical Chemistry

Branch/OPP 701 Mapes Road Fort George G. Meade, MD 20755 - 5350 (Note that the mail will be returned if the extended zip code is not used.) 860.1850 Confined Accumulation in Rotational Crops Residue Chemistry Memo DP# 328216 , 1 0 /2 3/200 7 , W. Drew (PP#6F7051 and PP#6E7163) Resi due Chemistry Memo DP# 264154, 1 2 /31/2001, M . Doherty (PP#0F6082)Acetamiprid Summary of Analytical Chemistry and Residue Data DP#: 364833

Page 23 of 38 No new confined rotational crop data were submitted with this petition ; the nature of the residue in rotational crops is understood . A confined rotational crop study was reviewed in conjunction with PP#0 F6082. In the study , acetamiprid was not detected in any rotational crop matrix (mustard greens, radish, and grain crops) at any of the plantback interval s (PBI s), which were 30 - , 58 - , 120 - and 365 day s after treatment ( DAT) following application to bare soil at 0.66 lb ai/A . The major metabolite identified in rotational crops was IM - 1 - 4, at 2.94 - 56.65% TRR (<0.001 - 0.040 ppm). Two other metabolites were identified in most rotational crops: IM - 0 - Glc, at 1.11 - 15.23% TRR (<0.001 - 0.010 ppm) , and I C - 0, at 2. 75 - 24.19% TRR (<0.001 - 0.014 ppm). S torage stability data , required as a condition of registr ation in the original petition PP#0F6082 , have been submitted and determined to rectify deficiencies under PP#6F7051. HED has determined that the residue of con cern in rotational crops is parent only , and that tolerances would not be needed on rotational crops. The available rotational crop data are adequate to support the uses proposed in this petition. 860.1900 Field Accumulation in Rotational Crops Residu e Chemistry Memo DP# 328216 , 1 0 /2 3/200 7 , W. Drew (PP#6F7051 and PP#6E7163) No field rotational crop data have been submitted, and no rotational crop restrictions have been proposed. The available confined rotational crop data indicate that no field rotational crop studies or label restrictions for rotational crops are required to support the proposed uses. 860.1550 Proposed Tolerances Tolerances are currently

established under 40 CFR §180.578 ( a)( 1 ) for residues of the insecticide , acetamiprid, in or on crop matrices. The tolerance expression proposed by IR - 4 in this petition is consistent with 40 CFR §180.578 (a)(1) . Adequate field trial data were submitted for clover. Provided confirmatory data are submitted as a condition of re gistration, the available field trial data will support the proposed regional tolerance s for residues of acetamiprid in clover forage at 0.10 ppm and clover hay at 0.01 ppm. The tolerance spreadsheet in the Agency ’s Guidance for Setting Pesticide Toleranc es Based on Field Trial Data was utilized for determining the appropriate tolerance level for clover forage; see Appendix I . The tolerance spreadsheet was not used to determine the tolerance level on clover hay because all treated samples (n=6) bore resid ues below the LLM V (<0.01 ppm). The submitted field trial data for grapes are ad equate pending label revision to remove use of a spreader, methylated seed oil or crop oil f rom the product label of Assail® 30 SG . The available grape field trial data from the current submission, which reflect a higher seasonal rate and a shortened PHIfrom th ose which are currently registered on grapes , will support the proposed tolerance for residues of acetamiprid in “ fruit, small, vine climbing, subgroup 13 - 07F, except fuzzy kiwifruit ” at 0.35 ppm. The tolerance spreadsheet in the Agency ’s Guidance for Setting Pesticide Tolerances Based on Field Trial Data was utilized for determining the appropriate tolerance level for grape; see Appendix I . The established individual tolerance for grape at 0.20 ppm should be concomitantly removed upon the establishment of the Subgroup 13 - 07F (except fuzzy kiwifruit) tolerance . HED notes that side - by- side trials on grapes comparing residues from the WP and SG formulations are recommen ded as a condition of registration.Acetamiprid Summary of Analytical Chemistry and Residue Data DP#: 364833

Page 24 of 38 Although the tomato greenhouse trials were conducted at 2x and the number of trials is marginal, the submitted data indicate that the established tolerance for residues of acetamiprid in fruiting vegetables (Crop Group 8) at 0.20 ppm will not be exceeded following applications of Tristar® 30SC according to the use pattern s o f the tomato greenhouse trials. HED notes that side - by- side trials on tomatoes comparing residues from the WP and SG formulations are recommended as a condition of registration. Acceptable grape and tomato processing studies are available. The grape processing studies reported processing factors of 1.5x for juice and 0.9x for raisins. The tomato processing studies reported processing factors of 1.4 x for puree and 3.0x for paste. Based on these data, no tolerances are needed in grap e raisins and tomato puree as a result of proposed uses because any expected residues in these processed commodities are estimated to be less than the respective RAC tole rances. Based on the observed processing factor of 3.0x and a HAFT of 0.1 ppm, a tolerance of 0.40 ppm w as established under 40 CFR §180.578[ a ][ 1 ] for residues of acetamiprid in tomato paste; this tolerance remains appropriate with the proposed use on gre enhouse tomatoes . Considering that the maximum theoretical concentration factor for grape juice is 1.2 (Guideline 860.1520), HED also expects residues in grape juice, resulting from the proposed use, will not exceed the RAC tolerance of 0.35 ppm; therefo re, a separate tolerance is not needed for grape juice. Although the tolerance spreadsheet recommends a 40 ppm level for dried tea, one residue value (40.9 ppm) exceeded that level and Japan has an established 50 ppm MRL for tea. Therefore, HED recommend s a 50 ppm tolerance as well. Given the data for brewed tea and understanding that FDA would adjust residues measured on instant tea back to a dried tea basis for enforcement purposes, a separate instant tea tolerance is not required The established t ole rances on animal commodities need not be reassessed for this petition. The proposed use on clover could theoretically lead to the secondary

transfer of acetamiprid residues of concern to beef and dairy cattle from the feeding of clov er forage, hay , and silage. However, the proposed use on clover is to be restricted to th at grown in ID, OR, and WA only and the residues on the clover RAC are very low . Therefore, HED does not believe that this would significantly

increase the dietary

b urdens. Tolerances on rotational crops are not needed. Residues of acetamiprid were not detected in any rotational crop matrix (mustard , lettuce , radish , sorghum , or wheat) at any PBI (30, 58, 120, or 365 DAT ). There are no Codex maximum residue limits ( MRL s ) establish ed for residues of acetamiprid o n crop or animal commodities ; no Mexican MRL s are established on crops associated with this petition. Canada has established an MRL for acetamiprid residues in grapes at 0.20 ppm. The recommended U.S. toler ance for Subgroup 13 - 07F tolerance at 0.35 ppm is not harmonized with the Canadian MRL , presumably because of differences in good agricultural practices. Japan has a 50 ppm MRLfor tea and HED recommends setting the tolerance at the same level. An Intern ational Residue L imit Status (IRL S ) sheet is appended to this document . The final tolerance for subgroup 13 - 07F should reflect the correct commodity definitions , as specified in Table 8 . A revised Section F does not need to be submitted for this minor ch ange.Acetamiprid Summary of Analytical Chemistry and Residue Data DP#: 364833

Page 25 of 38 Provided that the forthcoming human health risk assessment does not identify any issues of concern, the submitted data support the establishment of permanent tolerances for acetamiprid, including its metabolites and degradates under 40 CFR §180.57 8, as listed in Table 8, below. Compliance with tolerance levels specified below is to be determined by measuring acetamiprid o nly . Table 8 . Tolerance Sum ma ry for Acetamiprid. Commodity Established/Proposed Tolerance (ppm) Recommended

Tolerance (ppm) Comments ; C orrect Commodity D efinition Clover, forage 0.10 0.10 Recommended tolerances are for regional registration . Clover, hay 0.01 0.01 Fruit, small, vine climbing, except fuzzy kiwifruit, subgroup 13 - 07F 0.35 0.35 Pending label revision to remov e use of a spreader, methylated seed oil or crop oil. Fruit, small, vine climbing, except fuzzy kiwifruit, subgroup 13 - 07F . Grape 0.20 Remove Grapes will be covered under the subgroup 13 - 07F tolerance. Tea , dried 50 .0 50.0 Tolerance without a U.S. regi stration. References D 342549 / 355773 . Acetamiprid. Request for L abel Amendment (TriStar 30SG) Allowing Food/Feed Use of the Insecticide on Vegetable Transplants; Independent Laboratory Validation Study (Assail 70WP), Submitted as Supplementary Data Pursuant to HED Memorandum of 5 November 2004 (D303623). W. Drew , 11/05/2008 . MRID: 47185401 . D328216 . Acetamiprid. Petitions Requesting the Establishment of Permanent Tolerances (Associated with Section 3 Re gistration) for New Food/Feed Uses of the Insecticide on Berries (Crop Group 13), Bulb Vegetables (Crop Group 3), Edible Podded L egume Vegetables (Crop Subgroup 6A), Succulent Shelled Pea and Bean (Crop Subgroup 6B), and Strawberry and Other Lo w - growing Be rries. Summary of Analy tical Chemistry

and Residue Data. Petition Numbers 6F7051 (Various Crops) and 6E7163 (Strawberry ). W. Drew , 10/23/2007 . MRIDs: 46785502 - 46785504 and 47013601 D303623 . Acetamiprid. Tolerance Petition Requesting Section 3 Registration for Food Use of the Insecticide Acetamiprid on Cucurbit Vegetables (Crop Group 9), Stone Fruits (Crop Group 12), and Tree Nuts (Crop Group 14). Summary of Analy tical Chemistry

and Residue Data. Petitio n Number 4F6833. W. Drew , 11/05/2004 . MRIDs: 46265701 - 46265703 . D306191 . Acetamiprid. Tolerance Petition Requesting Section 3 Registration for Food Use of the Insecticide Acetamiprid o n Tuberous and Corm Vegetables (Crop Subgroup 1C) and Non Food Use on Tobacco. Summary of Analy tical Chemistry

and Residue Data. Petition Number 3F6575. W. Drew , 11/03/2004 . MRIDs: 45900506 - 45900509 .Acetamiprid Summary of Analytical Chemistry and Residue Data DP#: 364833

Page 26 of 38 D26415 4 . 0F6082. Section 3 Registration for Use of Acetamiprid on Cotton, L eafy Vegetables, Cole Vegetables, Fruiting Vegetables, Citrus Fruits, Pome Fruits, Grapes, and Canola and Mustard Seed. Summary of Analy tical Methods and Residue Chemistry DERs. M. Do herty , 12/31/2001 . MRIDs: 44988518 - 44988524, 44988526, 44988529, 44988532 - 44988535, 44988601 - 44988603, 44988610, 44988611, 44988616, 44988618 - 44988623, 4498862 . D278652 . Acetamiprid. Results of the HED Metabolism Assessment Review Committee M eeting He ld on October 16, 2001 . H. Bietlot, M. Doherty , and P. Hurley , 11/13/2001 . MRID : None . Attachments: International Residue L imit Status sheet Appendix I - Tolerance Assessment CalculationsAcetamiprid Summary of Analytical Chemistry and Residue Data DP#: 364833

Page 27 of 38 

## INTERNATIONAL RESIDUE LIMIT STATUS Chemical Name: Common Name: Acetamiprid X Proposed tolerance  Reevaluated tolerance  Other Date: 07/06/2009 Updated: Oct 5, 2009 with the tea MRL information. Codex Status (Maximum Residue Limits) U. S. Tolerances X No Codex proposal step 6 o r above  No Codex proposal step 6 or above for the crops requested Petition Number: 9E7544 DP Barcode: D364833 Other Identifier: Residue definition (step 8/CXL): N/A Reviewer/Branch: Dennis McNeilly /RAB2 Residue definition: acetamiprid [N1 - [( 6 - chloro - 3 - pyridyl)methyl] -N2 - cyano -N1 - methylacetamidine] Crop (s) MRL (mg/kg) Crop(s) Tolerance (ppm) Clover, forage 0.10 Clover, hay 0.01 Fruit, small, vine climbing, except fuzzy kiwifruit, subgroup 13 - 07F 0.35 Tea 50.0 Lim its for Canada Limits for Mexico  No Limits  No Limits for the crops requested  No Limits X No Limits for the crops requested Residue definition: (E ) -N - [(6 - chloro - 3 - pyridinyl)methyl] -N’ - cyano -N - methylethanimidamide Residue definition: acetamip rid Crop(s) MRL (mg/kg) Crop(s) MRL (mg/kg) Grapes 0.2 Notes/Special Instructions: S. Funk, 07/07/2009. Note: There are no MRLs for acetamiprid in Codex. There is no MRL for acetamiprid on tea in Australia. There is no MRL for acetamiprid on tea in Canada. Japan has a 50 ppm MRL for tea. Rev. 1998Acetamiprid Summary of Analytical Chemistry and Residue Data DP#: 364833

Page 28 of 38 Appendix I Tolerance Assessment Calculations Clover forage The dataset used to establish a tolerance for acetamiprid on clover forage consisted of field trial data representing a single application at rates of 0.074 - 0.079 lb ai/A with a 28 - to 34 - day PHI . As specified by

the Guidance for Setting Pesticide Tolerances Based on Field Trial Data (SOP), the field trial application rates and PHI s are within 25% of the maximum label a pplication rate and minimum label PHI , respectively . The residue values that were entered into the tolerance spreadsheet are provided in Table I - 1. 2 of 6 field trial sample results were below L OQ (LOQ = 0.01 ppm) , entering the LOQ and using maximum like lihood estimation (MLE) procedures for the censored values both yielded a recommended tolerance of 0.1 ppm . V isual inspection of the logno rmal probability plot (Figure I - 1 ) and the result from the approximate Shapiro - F rancia test statistic (Figure I - 2 ) in dicated that the assumption of lo gnormality should be rejected. Since the field trial data for acetamiprid on clover forage are not lognormal, the upper bound on the 89 th percentile should be selected as the tolerance value (distribution - free method) . Us ing the rounding procedure as outlined in the SOP, the upper bound on the 89 th percentile rounds to the value 0.10 ppm . Therefore, 0.10 ppm is the recommended tolerance level for acetamiprid in/ on clover forage. Table I - 1. Residue data used to calculate tolerance for acetamiprid on clover forage. Regulator: EPA Chemical: Acetamiprid Crop: Clover Forage (MLE) PHI: 28 - 34 Days App. Rate: 1 at 0.074 - 0.079 lb ai/A Submitter: IR - 4 MRID Citation: MRID 47716901 Residues of Acetamiprid (ppm) 0.05 0.04 0.05 0.05 0.0 1 0.0 1Acetamiprid Summary of Analytical Chemistry and Residue Data DP#: 364833

Page 29 of 38 Figure I - 1 . Lognorm al probability plot of acetam iprid field trial data for clover forage.Acetamiprid Summary of Analytical Chemistry and Residue Data DP#: 364833

Page 30 of 38 Figure I - 2. Tolerance spreadsheet sum ma ry of acetamiprid field trial data for clover forage . Re gul ator : EPA Ch em ical : Py

metr ozi ne Crop : Le afLe ttu ce PHI : 0-1 Day Ap p. Rate : Su bmi tter : n: 6 min : 0. 01 max : 0. 05 me dian ; 0. 05 ave rage : 0. 04 95th Pe rcentil e 99 th Per cen tile 99. 9th Per cen til e 0. 07 0. 09 0.1 0 (0 .15) (0. 15) (-- ) 0. 15 0. 20 0.3 5 (0 .60) (1. 7) (-- ) 0. 10 0. 10 UPLMe dian 95t

h 0. 60 0.7 235 0. 05 >=

p-v alu e > 0.0 1 : Rej ect log nor mal ity ass umpt ion Ap pr oxim

ate Sha pir o-Fr anc ia No rmal ity

Te st EU Me thod I I Distrib

utio n-F ree Cali fornia Met

hod μ + 3 σ EU M etho d I No rma l EU M etho d I Log Nor

mal

Grapes The dataset used to establish a tolerance for acetamiprid on grape consisted of field trial data representing application rates of 0.195 - 0.206 lb ai/A (2 applications at ~ 0.10 lb ai/A/application) with a 2 - to 3 - day

PHI . As specified by

th e Guidance for Setting Pesticide Tolerances Based on Field Trial Data (SOP), the field trial application rates and PHI s are within 25% of the maximum label application rate and minimum label PHI , respectively . The residue values that were entered into the tolerance spreadsheet are provided in Table I - 2. All 36 field trial sample results were equal to or greater than the L OQ (LOQ = 0.01 ppm). V isual inspection of the logno rmal probability plot (Figure I - 3 ) and the result from the approximate Shapiro - F ranc ia test statistic (Figure I - 4 ) indicated that the assumption of lognormality should be rejected. Since the field trial data for acetamiprid on grape are not lognormal, the upper bound on the 89 th percentile should be selected as the tolerance value (dis tribution - free method) . Using the rounding procedure as outlined in the SOP, the upper bound on the 89 th percentile rounds to the value 0.35 ppm . Therefore, 0.35 ppm is the recommended tolerance level for acetamiprid on grape. Table I - 2. Residue data u sed to calculate tolerance for acetamiprid on grapes.Acetamiprid Summary of Analytical Chemistry and Residue Data DP#: 364833

Page 31 of 38 Regulator: EPA Chemical: Acetamiprid Crop: Grape PHI: 2 - 3 Days App. Rate: 2 at 0.10 lb ai/A/application Submitter: IR - 4 MRID Citation: MRID 47716902 Residues of Acetamiprid (ppm) 0.050 0.05 0 0.030 0.030 0.010 0.010 0.080 0.080 0.170 0.150 0.080 0.090 0.080 0.080 0.200 0.210 0.240 0.250 0.100 0.110 0.060 0.060 0.220 0.220 0.040 0.040 0.070 0.060 0.040 0.030 0.150 0.150 0.240 0.22 0 0.130 0.130Acetamiprid Summary of Analytical Chemistry and Residue Data DP#: 364833

Page 32 of 38 Figure I - 3. Lognorm al probability plot of acetam iprid field trial data for grape. Lognormal Probability Plot

99.9 99 98 95 90 80 70 50 30 20 10 5 2 1 0.1 1.0000 0.5000 0.2500 0.1250 0.0625 0.0313 0.0156 0.0078 y = 0.8301x - 2.4867 R 2 = 0.9355

PercentilesConcentrations EPA Acetamiprid Grape 2-3 Days 2 at 0.10 lb ai/A IR-4

Figure I - 4. Tolerance spreadsheet sum ma ry of acetamiprid field trial data for grape .Acetamiprid Summary of Analytical Chemistry and Residue Data DP#: 364833

Page 33 of 38 Regulator: EPA Chemical: Acetamiprid Crop: Grape PHI: 2-3 Days App. Rate: 2 at 0.10 lb ai/A Submitter: IR-4

n: 36 min: 0.01 max: 0.25 median: 0.08 average: 0.11 95th Percentile 99th Percentile 99.9th Percentile 0.25 0.30 0.35 (0.30) (0.35) (--) 0.35 0.60 1.2 (0.60) (1.1) (--) 0.35 0.35 0.40 0.9355 0.05 >= p-value > 0.01 : Reject lognormality assumption Approximate Shapiro-Francia Normality Test EU Method I Normal

UCLMedian95th 95/99 Rule EU Method II Distribution-Free Mean+3SD

Tea The dataset used to establish a toleranc e for acetamiprid on tea consisted of a report summarizing the results of two studies on tea conducted in Japan (by Nippon Soda Co., Ltd.) and India (by the In stitute of Himalayan Bioresource Technology ; IHBT), submitted by the Interregional Research Proje ct No. 4 (IR - 4). The dataset used to establish a tolerance for acetamiprid on tea consisted of field trial data representing application rates of 0. 022 - 0.27 lb ai/A (1 foliar application) with a 6 - to 14 - day PHI . As specified by

the Guidance for Setting Pesticide Tolerances Based on Field Trial Data (SOP), the field trial application rates and PHI s are within 25% of the maximum label application rate and minimum label PHI , respectively . The residue values that were entered into the tolerance spreadsheet are provided in Table I - 2. T he common moiety

method used in the Japan study included the m etabolite I C - 0 which is not a residue of concern for tolerance enforcement or risk assessment but , based on the available plant metabolism studies, it may constitute a significant portion of the total residues (e.g., up to 24% total radioactive residues (TRR) in cotton seed and 31% TRR in carrot flesh; refer to D278652, 11/13/01, H. Bietlot and M. Doherty ). Therefore, the residues reported for the Japan study may ref lect an overestimation of expected residues of acetamiprid per se in green tea.

All 3 8 field trial sample results were equal to or greater than the LO D (LO D = 0.0 5 ppm). V isual inspection of the logno rmal probability plot (Figure I - 3 ) and the result f rom the approximate Shapiro - F rancia test statistic (Figure I - 4 ) indicated that the assumption of lognormality should be rejected.Acetamiprid Summary of Analytical Chemistry and Residue Data DP#: 364833

Page 34 of 38 Since the field trial data for acetamiprid on tea are not lognormal, the upper bound on the 89 th percentile should be selec ted as the tolerance value (distribution - free method) . Using the rounding procedure as outlined in the SOP, the upper bound on the 89 th percentile rounds to the value 40.0 ppm . However, one residue value is above the 40 ppm level (40.9 ppm) and Japan has already

establis h ed a 50 .0 ppm MRLfor acetamiprid on tea ; therefore, HED recommends for a 50 ppm tolerance . Given our understanding that FDA would adjust residues measured on instant tea back to a dried tea basis for enforcement purposes, HED believes that the 50.0 ppm tolerance for dried tea is adequate to cover residues in or on instant tea and hence is not recommending for a separate instant tea tolerance. HED notes that the 50.0 ppm tolerance harmonizes with Japan. The residue data from Japan incl uded the I C - 0 metabolite, which is not in the U.S. tolerance expression and therefore the data are considered conservative.Acetamiprid Summary of Analytical Chemistry and Residue Data DP#: 364833

Page 35 of 38 Table I - 3 . Residue data used to calculate tolerance for acetam iprid on tea. Regulator: EPA Chemical: Acetamiprid Crop: Tea PHI: 6 - 14 Days App. Rate: Submitter: IR - 4 MRID Citation: MRID 47781201 Residues of Acetamiprid (ppm) 16.4 17.2 8.15 8.45 16.5 16.7 13.6 14.0 9.32 9.78 0.24 0.15 0.07 0.51 0.42 0.23 0.68 0.45 0.21 1.47 1.21 0.62 0.2 0.12 0.06 0.38 0.26 0.15 0.54 0.38 0.18 1.1 0.67 0.38 37.7 40.9 22.5 23.6Acetamiprid Summary of Analytical Chemistry and Residue Data DP#: 364833

Page 36 of 38 Figure I - 4. Lognorm al probability plot of acetam iprid field trial data for tea.

Lognormal Probability Plot

99.9 99 98 95 90 80 70 50 30 20 10 5 2 1 0.1 41.0000 20.5000 10.2500 5.1250 2.5625 1.2813 0.6406 0.3203 0.1602 0.0801 0.0400 y = 1.9873x + 0.3103

PercentilesConcentrations EPA Acetamiprid Tea 6-14 DaysAcetamiprid Summary of Analytical Chemistry and Residue Data DP#: 364833

Page 37 of 38 Figure I - 5. Tolerance spreadsheet sum ma ry of ac etamiprid field trial data for tea . Regulator: EPA Chemical: Acetamiprid Crop: Tea PHI: 6-14 Days App. Rate: Submitter:

n: 38 min: 0.06 max: 40.90 median: 0.65 average: 6.99 95th Percentile 99th Percentile 99.9th Percentile 25 35 40 (30) (40) (--) 40 160 750 (110) (580) (--) 30 40 3.5 0.9046 p-value <= 0.01: Reject lognormality assumption Approximate Shapiro-Francia Normality Test EU Method I Normal

UCLMedian95th 95/99 Rule EU Method II Distribution-Free Mean+3SDAcetamiprid Summary of Analytical Chemistry and Residue Data DP#: 364833

Page 38 of 38 Re gul ator : EPA Ch em ical : Ac etam ipr id Crop : Te a PHI : 7- 14 Day s Ap p. Rate : Su bmi tter : n: 38 min : 0. 06 max : 40. 90 me dian ; 0. 65 ave rage : 6. 99 95th Pe rcentil e 99 th Per cen tile 99. 9th Per cen til e 25 35 40 (3 0) (4 0) (-- ) 40 16 0 750 (1 10) (58 0) (-- ) 30 40 UPLMe dian 95t

h 3. 5 0.9 046 p-v alue <=0.0 1: Rej ect log norm ali ty assumpt ion Ap pr oxim

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