UN ITED STATES ENV IRONM ENTAL PRO TECTION AGENC Y WASHINGTON , D.C. 20460



### MEMORANDUM DATE : April 20, 2016 OFFI CE OF C HEMI CA L SA F ETY AND POLLUTION P REVE N T I ON



### SUBJECT: Chlorantraniliprole (DPX-E 2Y45): Petiti o n for Updating Crop Group Tolerances for N ut Tree Group 14-1 2 and Fruit Stone Group 1 2- 1 2 , and Amending Establi she d Tolerances for Chlorantraniliprole in/on Artichoke G lobe and Hop Dried Cone s. PC Co d e : 090100 Dec is ion No.: 506095 P et ition No

. : 5E8371 Risk Assessment Type: NA TXRNo.: NA MRIO Nos. : 4950450 I ; 49504502


### FROM: Johnnie 

### L Smith 

### II , Chemist Risk Assessme nt Branch III Health Effects Di v ision (7509 P) DP Barcode: 0428081 Registration Nos.: 352-72 9; 352-730 R eg ulatory Action: Sec tion 3 Registration Case No.: NA CAS No.: 500008-45- 7 40 CFR : § 180.628



### THROUGH: Donald Wilbur, Senior Chem i st

# U,_**~** Christine Oling er, Branch Chief 

# /7. / :// , Risk Assessment Branch Ill 

# 0 0 ./- c:/ 

## L__ Health Effects Division (7509P) 

### TO: Barbara Madden Mino r Use and Emergency Response Branch Registration Division (RD ; 7505P)
I. 

### ACTION REQUESTED In terregional Research Proj ect Number 4 (IR-4) has requested to lower the curre ntl y established tolerances for c hl orantran ilipro le in/on hops dried cones from 90 ppm to 40 ppm and g lob e artic hoke from 4.0 ppm to 2.0 ppm in order to harmoni ze with the Codex maximum residue limi ts (MRLs). Additionall y , the petitioner has requested to update the following crop group tolerances: stone fruit crop group 12 to 1 2- 12 (and lower from 4.0 ppm to 2

. 5 ppm) and tree nuts crop gro up 14 to 14 -12 (and lower from 0.40 ppm to 0.02 ppm). Upon estab li s h ment of the tolerances associated with PP 5E837 1 , lR-4 requested to remove the fo llowing existing tolerances in 40 CFR 180.628: Nut , tree , gro up 14 at 0.04 ppm; pistachio at 0.04 ppm ; fruit, Page 

### 1of 10stone , group 12-12 , except cherry , chickasaw plum , and damson plum at 4.0 ppm; cherry, sweet at 2.0 ppm; cherry , tart at 2.0 ppm; plum , chickasaw at 2.0 ppm; and plum , damson at 2.0 ppm. No new data was submitted for stone fruit crop group 1 2- 1 2 and tree nuts crop group 14-12. 

### II. CONCLUSIONS There are no outstanding deficiencies in the petition proposing tolerances for chlorantraniliprole in/on globe artichoke , tree nut gro up 14-12 , stone fruit group 12-12 , and hops dried cones. The crop field trial stu die s s ubmitted to support the proposed tolerances on hops , dried cones and artichokes are adequate. The previous chronic dietary assessment (food and drinking water) (0416093, Kristin Rury , 1 2/03/2013) included all of the additional commodities of Stone fruit group 12-12 and Tree nut group 14 -12 that w ill be added via the crop group updates herein. The dietary burdens (0404708, S.Funk, 09/10/2013) will not change as a resu lt of these commodities. The results of the last chronic analysis (acute and cancer exposure assessments were not needed) indicated that chron ic dietary (food and drinking water) exposure and ri s k i s not of concern to HED [i.e. , < 100% chronic population adjusted dose (cPAD)] for the ge ne ral U.S. population and all population subgroup s. Therefore , a new di e tary ri s k assessment is not needed as tolerance s are being lowered for harmonization. There is no hazard via the inhalation and dermal route s of expos ure so updated s hort

- and intermediate-term occupational or re sidential handler and postapplication assessments are not needed. Based on the information provided above , HED concludes that the aggregate exposure and risks as a result of the proposed uses will not increase and will be the same as those estimated in previous HED risk assessments. The available information s ubmitted by IR-4 is adequate to review the tol e rance amendment requests for the u se of chlorantraniliprole in or on g lobe artichoke , tree nut gr oup 14 -12, stone fruit gro up 12-12 , and hop s, dried cones actions (see OEC D MRL calculatio n s for hops , dried cones and globe artichokes) and harmoni z ing with Codex/Canada (see Table 1). A s ummary of the recommended tolerance s and revo cations may be fou nd in th e fo ll owing table

.

Page 2o f 10Commodity Established Tolerances Proposed Tolerance HBO-Recommended Tolerance Comments (ppm) (ppm) (ppm) Nut, tree , group 14-12 0.02 0.02 Crop group update. International harmonization Nu t, tree group 14 0.04 Remove Tolerance to be replaced by crop

group 14-12 Fruit, s tone group 12-12 2 .5 2.5 Crop group update. International harmonization Fruit, stone group 12 4.0 Remove Tolerance to be replaced by crop

group 12-12 Globe Artichoke 4.0 2

. 0 2.0 Hop s Dried Cones 90.0 40.0 40 Pistachio 0.04 Remove Covered by propose d crop group 14-12

tolerance C herry, sweet 2.0 Remove Covered by proposed crop group tolerance 12-12 Cherry, tart 2.0 Remove Covered by proposed crop group tolerance 12-12 Plum , chickasaw 2

. 0 Remove Cove red by proposed crop group tolerance 12-12 Plum, damson 2.0 Remove Covered by proposed crop g r

oup tolerance 12-12 

### III. DETAILED CONSIDERAT I ONS Stone Fruit an d Tree Nut Crop Gro u p Updates With respect to Tree nut group 14-12 , the petitioner bas proposed to low er existing tolerance to harmonize with Co de x and Canada and to upd ate the existing crop group tolerance from crop group 14 to crop group 14-12

. HED concludes that the existing residue chemistry data for tree nut group 14-1 2 (D407350, Steve Funk, 11/12/2 013 and D412169 , Steve Funk, 12/09 /2 013) support the request for crop group conversion and for lowering existing tolerance to 0.02 ppm to harmoni ze with Codex and Canada. The proposed lab el ame ndment s we re reviewed and considered in assoc iation with PP# 3E8170 (0407350) (Reg. # 352- 730).

Page 3of 10

### For the Stone fruit group 12-12 , the petitioner has proposed to lower the existing tolerance in order to harmonize with Canada and to remove individual tolerances for members of the crop group because all crop group members are requested at the same tolerance level. HED concludes that the existing residue chemistry data for sto ne fruit group 12

- 12 (D407350 , Steve Funk, 11 /12/2 013 and 0412169 , Steve Funk, 12/09/2 01 3) s upport the request for crop group conversion and for lowering existing tolerance to 2.5 ppm to harmonize with Canada. Harmonization with Codex is not possible, s ince the Codex MRL for stone fruits is lower than the US and Canada. Lowering the US tolerance could result in residues above the tolerances when following the US approved label. There are no proposed label amendments. Tolerance Reduction on Established Tolerances on Hop, Dried Cones and Artichoke, Globe 

### IR-4 submitted crop field data (MRJD 49504501, globe artichoke and MRJD 49504502 , hops dried cones) in support ofthis petition to lower the existing tolerances from 4 ppm to 2 ppm for globe artichoke and 90 ppm to 40 ppm for hops dried cones. Tolerances were originally established based on residue data translated from other crops. The nature of the re s idue s of chlorantraniliprole is adequately understood (parent compound only), and an acceptable analytical method is available for enforcement purposes. Summary of Studies (M

RJD 49504501 Chlo rantrani/ipro/ e: Magnitude of th e Res idue on Artichokes) 

### Four field trials for chlorantraniliprole on globe artichoke were conducted in the United States encompassing required North American Free Trade Agreement (NAFTA) Growing Regions (3 trials Castroville , CA and 1 trial Marinas , CA). The formulation used 

### in the study was Coragen (EPA Reg. No. 352-729) , a 1.67 lb ai/gal suspension concentrate formulation. At each trial , two foliar directed applications of the test s ubstance were made 14-16 days apart to the treated plots. The application rates ran ged from 0.100 to 0.109 lb ai/A per application for a total rate range of 0.200 to 0.209 lb ail 

### A/season. All applications were made usin g appropriate spray equipment , and the spray volume was sufficient to provide adequate dispersal of the test substance. Sampling s tarted in the untreated control plot and ended in the treated plot. At all the field trials, samples were harvested 3-4 days after the last application. The maximum storage interval for field-treated samples in this study was 620 day s. Storage stability samples were fortified with chlorantraniliprole at 1.0 ppm. The storage sta bilit y samples were held in frozen storage under similar conditions to the field generated samples. The storage stability samples were prepared to be analyzed in case of freezer failure. No storage stability data was obtained as part of this study since adequate storage stability data is available to demonstrate that chlorantraniliprole is stable in a variety of crop matrices when held in freezer storage for up to two years. The samples were analyzed u sing a work ing method very similar to the enforcement method ,

Page 4of10

### "Method Val id ation for the analysis ofDPX-E2Y45 in Various Crop Matrices;" Dupont Laboratory project ID : DuPont- 1 3294; Dated : March 22, 2004. Chlorantraniliprole residues were extracted from the macerated crops by blending w ith acetonitri le fo ll owing a pre-soak in water. After filtration , the vo lume of th e filtrate was adjusted with acetonitril e. An aliquot of the so lu tio n was evaporated to dryness and the residue was reconstituted in acetonitrile/water (40:60, v/v) for analysis by liquid chromatography/tandem mass spectrometry (LC/MS/MS)

. Recoverie s were in the range 87- 105%. The limit of detection ( LOD ) for the method was calculated to be 0.0087 ppm and the limit of quantitation (LOQ) was calculated to be 0.026 ppm. The lowest level of method validation (LLMV) fo r artic hoke was 0.05 ppm for chlorantrani li prole. The total residues of chlorantraniliprol e were in the range 0.462 to 0. 723 ppm in samp les take n at 3-4 days PHI. HE D concl ud es that the study is adequate to estab li sh the proposed tolerance of 2.0 ppm on globe artichokes. There are no proposed label amendments. A summary ofres idu es from g lobe artichoke field trials with chl orantraniliprole are presented in Table 

### 2 ; OECD calcul ator output for hops is presented in Attachment 1. Table 2. Summarv of Res idu es from G lobe Artich o ke Field T rials with Cbloraotranilipro le. Total Residues (ocm) Application PHI Crop Matrix Rate (days) n2 Min. 1 Max. 1 LAFT2 HAFT 2 Med ian 2 Mean 2 SD 2 ( lb s ai/A) Proposed Application Rate ; PHI Artichoke 0.200 to 3-4 4 0.462 0.723 0.477 0.690 0

. 565 0.574 0.091 0.209 1 Values based on total number of sa mple s. 2 Values based on per-trial averages. LAFT =lowest average field trial , HAFT= highest average field trial , S D = standard deviation. For computation of th e LAFT , HAFT , median , mean , and standard deviation, values < LOQ arc assumed to be at the LOQ (0.0 1 ppm); n = number of field trials.
(M RJD 49504502 Chlorantrani/iprole: Magnitude of the Residu e on Hops) 

### Four field trials for chlorantraniliprole on hop s dried cones were conducted in the United States ( I

daho, Oregon, and Washington) encompassing required NAFTA Growing Regions. Each field trial s ite con s isted of one untreated control plot and one treated plot. A non- ionic s ur factant , a methy l ated seed oil blend , a crop oil concentrate or an organosilicone s urfactant was used at each of the field trials 

### in thi s study. At each trial, 2 foliar applicat i ons of the test substance 7 to 8 days apart were made to the treated plots. The application rates ranged from 0.1 to 0. 103 lb a i

/A/a pplication for a tota l rate range of 0.20 1 to 0.206 lb ai/A/season. Al l app li cation s were made using appropriate spray eq uipment , and th e spray vol ume was s u ffic ient to provide adequate dispersal of the test substance. The h ops cones were harvested simulating commerc ial practices. Sampl ing started in the untreated control plot and ended in the treated plot. At all the field trials, samp les were harvested on th e day of the las t application. At the ID 04 and WA04 trials, ad ditional samp les were Page 5 of 10harve sted at 1 , 3 , 7

- 8, and 13

- 14 days after the las t application to provide decline data on the nature of c hlorantraniliprol e residues. After harvest , the hop cones were dried in o vens/dryer rooms/kilns s imulating commercial practice s. All s ample s were dried to commercially acceptable standard s. A ll samp les were analyzed fo r chlorantraniliprole re si due s only. The s torage interval for field-treated dried hop s cones in thi s s tudy ranged from 219 days to 238 day s. No storage stabilit y data was obtained as part of thi s s tudy si nc e adequate s torage stability data exi sts to d emon strate that chlorantraniliprole is s table in a variety of crop matrices w h en held in freez er s torage for up to two years. Sample s were analyzed for chlorantraniliprole u s ing the analytical method derived from the referenc e method titled " Method Validation for the Analy s is of OPX-E2Y45 in Various Matric es " ; DuPont Laboratory Project IO.: DuPont

- 1 3294 ; Date d: March 22, 2004. Recoveries were with in th e acceptable range of 70-120%

. C hlorantraniliprol e residues are extracted from the hop samp les firs t u s in g a mixture of water and ace to nitrile (ACN). The extract is cleaned up by Strata-X in tandem w ith NH2 so lid phase extraction c artridge s. The purified extract is diluted in ACN/ W ater (50/ 50 , v/ v) and then s ubmHte d to LC- M S/MS for analysis. The LOQ is 0.05 ppm. The LOO is d efined as 10% bel ow the smal lest concentration 

### within the standard curve. Chlorantrani liprol e res idue s in the treated samp les (0 day PHI ) ran ge d b etween 6.8 ppm and 19 ppm fo r s ample s harve ste d on the day of the la s t application. No de t ecta ble res idues (LLMV 

## = 0.0 5 ppm) of ch lorantrani li prole were found in the untreated co ntrol s ample s . At two of the trials , additional resi du e data was collected from samples harveste d at 1 , 3 , 7

- 8 , and 13

- 14 days after the l as t application. The decline data from both trials indicate d that the residues remained fairly stable between 0 and 3 days after treatment and th en d e clined

. HEO concludes that the study is adequate to establi s h the proposed tolerance of40 ppm on hops dried cone s. The l abel for hops dried cones (EPA Reg. # 352- 729) total ai/ acre/year rate will remain the sa me for this use . A s ummary ofresidues from hops field trial s with chlorantraniliprole are presented in Table 3 ; OECD calculato r output for hops is pre sented in Attachment 2

. Tab l e 3. Summary of Residues from Ho >S Field Trials with chlorantranilipro le. Total Res idues (ppm ) Application PHJ C ro p M atrix Rate ( days ) nl M' I Max

. 1 LAFT2 HAFT2 Median 2 Mean 2 

### so2 { lb s ai/ A) m. Proposed Application Rate ; PHI Hops 0.20 1 to 0 8 6
. 8 19 7 17

. 5 10

. 1 5 11.2 4.85 0

. 206 1 Values based on total number of s amples . 2 Valu e s bas ed on per-trial ave rages. LAFT = lowest average field tria l , HAFT = highe st ave rage field trial , S D = standard deviation

. For compu t a ti on of the LAFT, HAFT, median , mean , and standard dev iati o n, values< LOQ are assumed to be at th e Page 6of10LOQ (0

. 0 1 ppm) ; n = number of field trial s .



### IV. List of Attachment s • O EC D Calculator Output Globe Artichokes • OECD Calculator O utp ut Hops Dri ed Cones • International Harmonization



### Attach ment 1. O EC D Ca lculator Output G lobe Artichokes

C blorantraniliprol e

Globe Artichoke s 

### E

PA 0.209 lb ai/A; PHl =3-4 days
Total number of data (n) Percentage of censored data Number of non-censored data Lowest residue Hi ghest residue Median residu e Mean Standard deviation (SD) Correction factor for censoring (CF) Proposed MRL estimate

- Highest res idue

- Mean + 4 SD

- CF x 3 Mean Unrounded MRL
Rounded MRL High uncerta inty of MRL estimate. [Small dataset] 

### Page 7 of 10 4 0% 4 0.477 0.690 0.565 0.574 0.091 1.000

0.690 0.938 1 .722 1.722Residues (mg/kg) n 0.477 l 0.535 I 0.594 I 0.69 I



### Attachment 2. OECD Calculator Output Hops Dried Cones

Total number of data (n) Percentage of censored data Number of non-censored data Lowest residue Highest residue Median residue Mean Standard deviation (SD) Ch lorantraniliprole Hops dried cones 11112 I VS E

PA

Correction factor for censoring (CF) Proposed MRL estimate

- Highest residue

- Mean + 4 SD

- CF x 3 Mean Unrounded MRL
Rounded MRL
Hig h u ncertainty of M RL est imate. [Small d ataset)


### Page 

### 8of10 4 0% 4 7.000 17.500 10.150 11. 200 4.850 1.000

17.500 30.602 33.600 33.600Residues {mg/kg) n 7 1 7.8 1 12.5 1 17.5 1



### Attachment 3. International Harmonization 

### Chl t 

### T oran rant tpro e Summary of US and Internationa l To leran ces and Maximum Res idue L i mits of Cb l orantraniliprole R es idu e D efinition 

## us Canada Mexico2 C odex 3 40CFR§ 180.628

. For plant and animal 3-bromo

- N -[4- co mmodities : chlorantranil ipro le, 3- bromo-N- [4- c hl oro -2-met by1-6

- ch loro-2 -metby l-6- [(methylamino )carb o [(methylamino)carbo ny l]ph enyl ] -1 -(3 -chloro-2- ny1 ] phen y l]- 1-(3- Chlorantrani liprol e pyr idinyl) -1 H-pyrazo le-5-c arboxamide chloro-2- pyridiny l)

- (fat so luble) I H-pyrazole-5- carboxamide. Commodity 1 To le ran ce (oo m) / Max imum R esidue L imit (mJ!/kJ!) 

### us Canada M exico2 Codex 3 N ut, tree , group 14

- 12 0.02 0.02 0.02 Fruit, stone group 12- 12 2.5 2.5 1.0 Globe Artichoke 2 .0 2.0 2.0 H ops 40 Not Es tab li s hed 40

Co mpl eted: M .Neg uss ie; 04/14/ 16

1 In cl ude s only commoditie s of in terest fo r thi s action. T o le rance values shou ld be th e HED recomme ndation s and not tho se proposed by the applicant.



### Page 9of102 Mexico adopts US tolerances and/or Codex MRLs for its export purposes.
3 

### * = absent at the l im it of quantitation; Po = postharvest treatment, such as treatment of stored grains. PoP = processed p ostharvest treated commodity, such as processing of treated stored wheat. (fat) = to be meas ured on th e fat portion of the sample. MRLs indicated as proposed have not been finalized by the CCPR and the CAC.



### Page 

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