NAA Summary of Analytical Chemisrry and Residue Data DP # : D423409 

### UNITED STATES ENVIRONMENTAL PROTECTION AGENCY WASHINGTON , 

### D
. C
. 20460



### MEMORANDUM Date : Novembe r 

### 1 8 , 2015 OFFICE OF C H E MICAL SAFETY A ND PO LL U T ION PREVENTION



### S UBJ E CT: 1 -Naph th al e neace ti c ac id (NAA), it s sa lt s, este r, an d ace tamid e . Ne w Use in/o n Pomegr anate. 

### S u mmary of Ana ly tica l C h em i s t ry and Resid u e Data. PC C ode: 05600 1 , 056002, 056003 , 0560 04, 056007 , & 056008 D ec is io n No .: f./9511 1 P e ti t io n No .: 4E8310 Ri s k Ass e ss m e nt T y pe : NA TXR No.: NA DP Barc odc: 423409 Re g is trati o n No s .: 548 1-429 Re g u la tory A c tion: Sect ion 3 Ca s e No .: 0379 CAS No.: 86-87

- 3 M RID No s .: 4945100 I 40 CFR: 1 80. 1 55 

### F ROM: Thurs ton G. Morton, C h e mi s t Ri sk Assess m e n t B ran c h 4 Hea lth Effec t s Di v i s ion (7509 P) 

### THRO U GH: E lissa Reaves, Ph
. D
. , C h ief Ri sk Assess m e nt Bra n ch 4 H ea lth Effects Di v is ion (7509 P) A nd Danette Drew , Se ni o r C he m is t

# ~ RA B 5 7/ H E D , 75 0 9 P , C he m i§J ry Sc ie nce A d v i sory Co uncil (Ch e m S A C) Yvonne B arnes , C he mi st 

# r.**~ ~~**  RAB6/HE D , 7509 P , C hemSAC 

### TO: S idn ey Ja c k so n/B a rbara M a dd e n Risk In teg rati o n , M in o r Use 

### & E m erge ncy Res p o n se B ra n c h Registrat ion Di visio n (7505 P )

Page 1 of 11NAA Summ ary of Analytical Chem istry and R esidue Data DP # : 0423409


### Acti on Requested Under PP#4E83 l 0 , The In terregional Research Project Number 4 ( IR-4) has s ubmitted a petition for the es tabli s hment of a perm a ne nt tolerance for re s idue s of the plant growth regulator 1- Naphthaleneac e tic acid (NAA) for a Sec tion 3 r egistratio n of TRE-HOLD Sprout Inhibitor A 11 2. Th e pet iti o ner i s proposing the establi s hm ent of the fo ll owing p erman en t tol eran ce for res idu es of NAA: P omegranate ........................................................... .. ...... .. ........ 0.05 ppm 

### Dis c u ssio 11 1-Naphthaleneacetic ac id (NAA) , it s salt s, es ter , a nd acetamide are plant growth regulators ( PGR) w hich are collectively referred to as naphthal e ne acetates . The P G R activity of NAA is du e to it s structural s imilarity to the n atural plant horm o ne indole acetic aci d ( l AA). They are c urre ntl y registered fo r u se on variou s orchard and fruit crops to prevent preh arves t drop of fruits, thin fruit trees , and d e lay flow e r indu ction
. The y can a l so sti mulat e growth and delay le af drop on o rn a ment a l s. New re s idue chemistry data on pomegranate were s ubmitted to support the new u se . Res idues ofNAA we r e below the LOQ ( < 0.05 ppm) in/on p o megranate harv este d 45 days fo ll o win g two s pray appli cati o n s of a I % ai so lution of the 15.1 % EC fo rmul atio n of NAA ethyl este r. Tolerances are es tabli s hed und e r 40CFR § 1 80.155(a) fo r the residues of l-naphthal e neac et ic ac id , includin g it s metabolites and degradates in o r o n the co mm odi ti es. Comp lian ce w ith the tolerance le ve ls s p ec ified is to be dete nnin ed b y measuring only 1-naphthal e neac e tic ac id and it s co nju gates , calculated as the Stoic hi o metric equiva le nt of 1-naphthale n eac etic acid , in or o n the com m od ity. The estab li s he d tol e ranc es ran ge from 0.05 ppm to 2. 0 ppm. The c urre nt tol e ranc e express ion for NAA is in accord with o ur cu rrent g uidanc e. 

### Co n cl u s i on 

### HEO ha s examined the res idu e chem is try database for NAA. With re gards to NAA for PP#4E83 10 , pe ndin g subm ission of ana lytica l standards, th ere are no residue c hemi stry issues th at wou ld precl ude g ranting a Sect io n 3 reg istration for r esidues o f NAA onl y in/on th e following com modi ty: P omegranate ... . ................ . ....... ...... .. ........ . .. .. ...... ........... ..... ... ... 0.05 ppm A hum a n hea lth risk assess ment is fo rthc o min g.

Page 2of 11NAA Summary of Anal ytical Chemistry and R esid ue Data DP # : D4 23409 

### Backgrou n d The chemical structure a nd nomenclature of I n a phthaleneacetic acid (NAA) , its sa lt s, ester , and acetam id e and the physicochemical properti es are presented in Tab l es 

### I and 

### 2.
Table l. Nap h t h a l e n e Acetates No m e nclatur e C hemical s tru c ture 0 0
N ll 2 OH 

# I**~ ~**  

# I**~ ~** **~ ~** **~ ~**  Common name AA acctamidc AA Molecular Formula C1 2 H 11 0 C12 l !i o02 Molecu l ar Weight 1 85.23 1 86.20 IUPAC name 2-( 1-naphthy l )acc ta mid e 2-( 1-n ap hthy l)ace tic acid CAS nam e 1-n aph th alcneacctamide 1-n ap hth alcneacetic acid CAS# 86-8 6-2 86-87-3 PC Code 05600 1 056002 Chemical struc ture 0 0 • 

### - + 0 K 0 N H 4 

# I**~ ~**  

# I**~ ~** **~ ~** **~ ~**  Co mmon name NAA pot assium sa lt NAA ammonium sa lt Molecular Formula C12 H 1002 K C12 H 13 0 2 Molecular Weight 224 .3 1 203.24 IU

PAC name po tassi um - 2 ( 1-n ap hth y l)acetatc ammonium-2( 1-n aphthyl)acetate CAS name 1-naphth aln e ne ace ti c acid. po tass ium sa lt 1-naphth a l e n

eacc ti c ac id , ammonium sa lt CAS# 151 65-79-4 25545-89-5 PC Code 056003 056004



### Page 3o f11NAA Summary of Analytical Chemistry and Re sid ue Data DP # : D423409

Tabl e I. Naphth a l ene Ace tat es No m e n c l ature Chemica l s tru cture 0 Na

Co mm on nam t: NAA sodium salt NAA ethyl ester Molecular formula Molecular W eight 208.2 2 14.2 6 I U

PA C name sodiu m-2 ( 1-naphthyl )acetate ethyl

- 2( 1-naphthyl )ace tatc CAS name 1-Naphthalcncacctic acid. sodi um sa lt 1 -Naphthalencacetic acid. ethyl ester CA S # 61-31-4 2122-70-5 PC Code 056007 056008 Tabl e 2. Ph ys i coc h e mi ca l Pr o p e rti e s of NAA 1 P ara meter Va lue Ref e r e nce Active In gred i ent NAA aceta mid e Meltin g poin t/ ran ge 182-184 

### ° c Farm Chemicals 1 landbook p l I of I% aqueous suspensio n 5.1 Product CSF Density o r specific gravity 0.221 g/cm 3 Product CSF Water so lubility (20 C) not available Solvent so lubilit y (20 C) not available Vapor pressure at 20 C not available Dissociation constant (p K .) no t available Octanol/water partition coeffic i ent (Kow) not available UV /vis absorption spectrum not available Active ingredient NAA Meltin g point/range 13 0 

### °c Farm Chemicals 1 landbook pl I of I% aqueous suspension 3.45 RD 0265117. 5115 1 00. B. Kitchen s Den s ity or specific gravity 0.45 g/m L C B Nos. 3468 and 3469. 6/ 3/ 88. F. uhre Water so lubility (20 C) 0.042 g/ 100 mL C B Nos. 3468 and 3469. 6/ 3/ 88. F. Suhre Solvent so lubilit y (20 C) xylene 5.5 g/ I 00 mL C B Nos. 3468 and 3469. 6 /3/ 88. F. Suhre**CCI~** 1.06 g/ 100 mL freely so luble in aceto ne . ether. Parm C hcmical s I landboo k and chloroform Vapor pressure at 20 C 0.3 mm Hg at 26 

### °c C B Nos. 3468 and 3469. 6/ 3 / 88. F. Suhrc Dissociation con stant (pKa) 3. 16 x 1 0-' C O Nos. 3970 and 3971. 7 / 5

/ 88. F
. Suhrc Octanol/water partition coefficient (Kow) not applicable: polar compound UV / vis absorption spectrum not available Active ingredient NA A so dium s alt Me ltin g point/range >300 

### ° c 

# I C B Nos. 3468 and 3469. 6 / 3

/ 88. F. Suhre 

### Page 4 of 11NAA Summary of Analytical Chemistry and Residue Data DP # : D42 3409

Table 2. P h ys i coc h e mica l Properties o f NAA 1 Parame ter Va lu e Ref ere nce pl I of 1% aqueous s uspen sio n 9. 1 Cl3 Nos. 3468 and 3469. 6/3/88. F. Suhre Density or specific gravi t y 0.46 g/ mL CB Nos. 3468 a nd 3469, 6/3 / 88, F. Suhre Water so lubility (20 °q 340 g/ 100 mL CB Nos. 3468 and 3469, 6/ 3 / 88, F. Suhre So lvent solubility ( 20 °C) insoluble in n o npolar so lvents CB Nos. 3468 and 3469. 6 1 3 1

88, F. Suhre Vapor pressure at 20 ° c not available Dis so ciation constant (pKa) 3.16 x 10..s CB os. 3970 and 397 1. 7 1 51

88 , F. Suhre Octanol / water partition coemcient (Kow) not applicable: polar compound U

V

/vis absorption spectrum not available /\ctive ingredient NAA e th yl e st e r Boil in g point/range > 1 50 °c Old un-reviewed Un ion Ca rbid e data pl I of I % aqueous suspe nsio n not available Density or s pecific gravity I
. I I at 20 °C Old un-reviewed U nion Carbide data Water solubi lit y (20 °C) insoluble Old un-reviewcd Union Carbide data

. oh ent solubil ity (20 °C) soluble in xy lene. t oluene. Old un-reviewed Union Ca rbide data ethanol. acetone. and methyl ethyl ketone Vapor pressure at 20 °C not ava ilable Dissociation constant (pK
. ) not available Oc tanol/water partition cocnic i ent (Kow) not ava il able UV / vis absorption spec trum not available 1 No physicochemical properties information was available concerning the NAA potassium and ammonium salts. 

### 860 .1 2 0 0 Dir ec ti o n s fo r Use The petitioner has submi tt ed copies of the proposed labels for Tre-Hold Sprout Inhibitor A-112. Tre- H o ld Sprout Inhibitor A-112 is an em ul s i fiable concentrate formulation containing 15.1 

### % NAA , ethyl ester (I lb/ga l ae NAA). The proposed u se directions are pre se nted in Tab le 3 be low.

Tab le 3. S umm a r y of D irectio n s fo r Use o f NAA Applic. Timing , Max. No. Max. Fonnulation Applic
. Rate Seasonal PHI Type , and (lb ac/ gal) Applic. per Applic. Rate (days) Equip. Season ( lb ae/gal) Pomegranate TRE-Hold Spro ut Inhibitor A- 0.078 lb ac/ gal two per I 12, EPA Reg. No. 548 1 -429; 10 oz. 45 days 15.1 % NAA , e th y l es ter ( I lb product/gallon year 0.156 Directed sp ra y implied to the lower ae /ga l ) ( ! % w / v) tree trunks Use Directions and Limitations: Treat early before suckers attain 12" in length. Best results are attained when first treatment is made after the trees resume growth and sucke rs become visible. A minimum 60-day RTI is specified. The REI is 12 hours. Aerial application is prohibited. 

### Co nclusion. The proposed u se direction s are adequa te to allow evaluation of the re s idue data relative to the propo se d u ses . Page 5of11NAA Summary of Analytical Chemi stry and R es idu e Data DP # : D423409



### 860.1300 Na tu re of the Res idu e - Plants RED Residue Chemistry Chapter D299296 , 10 MA R CH 2004. G. Otakie Acceptable appl e a nd olive m e taboli s m s tudi es have been previous ly s ubmitt e d and reviewe d. B ased on the n atu re of residues identified from the app le and ol ive metabo li s m s tudi es, H ED has prev iou sly determined that the terminal residu es of concern in p lant s are th e parent compounds , NAA and its conjugates an d that the qualitative nature of the re s idu es in plants ( i. e., o rchard trees) is adequate ly und e rs tood. For purpose s of th e c urre n t petition the nature of the re s idu e in p la nt s i s adequately und e r s tood. 

### 860.1300 Na ture of the Residue - Livestock RED Residue Chemisrry Chapte r D299296 , 1 0 MARCH 2004, G. Otakie An acce pt able goat met abo li sm s tud y ha s b ee n previously s ubmitted a nd reviewed. Ba sed o n th ese data , HED has prev io u s l y co nclud ed that th e qua li tative natur e of th e r es idu e in rumin ants i s adeq u a te ly understood. The terminal residues of conce rn in ruminants are the parent compo und s, NAA and it s conjugates. T he available ruminant metabolism data are adequate to support the proposed u ses. There a re no poultry fe e d items associated with curre ntly reg i stered or proposed food u ses ofNAA; thu s a poultry m etabo li sm study is not required. 

### 860.134 0 Residue Analytical Methods RED R esi du e Ch e mi s try Chapt er D299296, I 0 MARCH 2004, G. Otakie 

### Enforcemen t and data collection m ethods: The re sid ue analytical me thod s, c urre ntl y li s ted in V o lum e II of th e Pes ticid e Analytical Method s , are in a dequ ate for th e e nforce me nt of tolerances for residues of 1-naphth a le nea cet ic a c id ( Pest icide R eg . Sec. 180.1 55) and 1- naphthal e neacetamide (Pesticide Reg. Sec. 180 .3 09) in / on plant commodities becau se th ese methods use benzene , a hazard o u s o r tox ic re age nt. An HPL C meth o d usin g fluor esce nce detection (Method NAA-AM-001) fo r a ppl es and peas and a s imilar method fo r o li ves and o li ve oi l (Me th od NAA

- AM-002) h as be en previously subm itted fo r determination of NAA in plant commoditi es . These me thods includ e extrac tion w ith water and incorporate a basic hydro lysis step to rel ease bound residues. These me thod s do not use benzene or diazo meth ane w hj c h are b e in g di sco urag ed by the Agency for safety reaso n s . T hese s me thod s h ave been subjected t o s ucce ss ful ind e pend e nt lab o ratory va lidati o n s . Acceptab l e recoveries were obtain ed from apples , o lives and olive oil fo rtified w ith NAA at th e me th od LOQ ( 0.0 l ppm) and at 1 .0 ppm . Thi s method is s uit able fo r e nforceme nt.
P o me g ranate sample s we re analyzed fo r re s idu es of NAA u s in g hi g h performance liquid
Pa ge 6of11NAA Summary of Analytical Chemistry and Residue Data DP # : D423409 chromatography with fluorescence detectio n (HPLC/UV) adapted from Morse Laboratories , Inc. analytical method NAA-AM-003. The m e thod is a common moiety method that converts residues ofNAA acetamide and NAA ethyl ester to NAA. The limit of quantitation (LOQ; determined as the lowest level of method validation, LLMV) was 0.05 ppm. Acceptable method validation and concurrent recoveries [Concurrent recoveries were below the acceptab le range of 70% ; 61 % for NAA , and 60% for NAA-EE.] were reported for samples of pomegranate fortified with NAA and NAA ethy l ester at 0.05-1.0 ppm , thu s vali dating th e m ethod. The fortification leve ls used in concurrent method recovery were adequate to bracket expecte d residue levels. Concurrent r ecove ries and residues in the treated samples were not correc t ed for residues in controls. 

### 860.1360 Multire s idue Methods 0232463 , 0294854, 30 OCT 2003, G. Otakie Multiresidue method ( MRM ) data have been submitted pre v iously in suppo rt of the registration ofNAA , its sa lts , este r and acetamide
. Naphthaleneacetamide was found to chromatograph satisfactori ly using Pesticide Analytical Manual (PAM) Vol. I, Sect ion 302 DG 5. Naphthaleneacetam ide was found to produce a 50% fu ll sca le deflection (FSD) with a 50 nanogram injection and the relative retention time to chlorpyrifos is approximate ly 0.8. Average recoverie s for naphtha leneacetam ide spiked into pears at approximately 0.1 ppm and 1.0 ppm were 97.8 and I 04% , respectively , for Section 302 , method E I , without F lori s it cleanup. Apple spikes u s in g this procedure co uld not be quantified due to interference in the app le matrix. Naphthaleneacetam i de was fo und not to be recoverab le through Florisil , so it wou ld not be recoverable through Protoco ls E o r F. Therefore , testing under P AM Vol. I Protocol E , for apples and pears , and Protoco l F , for olives , was suspended prior to recovery experiments through the entire Sections 303 and 304 methods. FDA MRM's are not suitab le as e nforcemen t method s for NAA. 

### 860.1380 S tora ge Stability RE D Re s idu e C hemistry Chap ter 0299296 , 10 MAR C H 2 004 , G. Orakie Adequate storage stab ili ty data have been submitted and re v iewed for app les , pears , and olives. These data indicate that re s idues of 1-naphtha leneacet ic ac id are reasonably stab le under frozen storage co ndition s in/on the above commodities for up to 1 2 month s . In addition , storage stabi li ty data s howed NAA and NAA ethyl ester stored in frozen avocado were s table for up to 27 month s and stored in froze n Rambuttan for up to 25 month s. All pom egranate samples for the current submission were maintained frozen at the testing facilities , during shipp in g , a nd were stored fro ze n at th e ana lyt ical laboratory until analysis. The maximum s torage interval for samp l es betwee n harvest and ex traction was 23 1 days (7.6 month s)
. Samples were analyzed within 5 day s of extraction. Concurrent recoveries were be low the acceptable range, 6 1 % for NAA (see MRID # 4945100 I , p.154) , and 60% for NAA

- EE (p.149 )
. Sto rage stabil i ty data generated concurrently wi th the field trial study demonstrate that residues of NAA and NAA ethyl ester, resp ec tively , are stab le in/on samples of pomegranate Page 7of 11NAA Summary of Analytical Chemistry and Re s idue Data OP # : 0423409

s tored frozen for up to 240 and 248 da ys (7.9-8.2 months) ; no 0-day data were provided. These data are acceptab le to support the s tora ge conditions and durations of sampl es from the submitted field tria ls; however, storage stabi li ty s tudie s should always include a 0-day sa mpling interval to es tablish the r esid ue level s pre sent at the time sam ples are placed in to s tora ge [see OPPTS 860.1380(d )( 6)(i)]. 

### 860.1400 Water , Fish, and Irrigated C rop s There a r e no propo se d u ses that are re levant to this gu id e li ne topic. 

### 860.1460 Food Handlin g There are no propo se d uses that are rel evant to thi s guide li ne topic. 

### 860.1480 Meat, Milk, Po ultry, and Eggs RED Res idue C hemi s try Chapter 0 29929 6 , I0 MARC H 2004, G. Otakie Live s toc k There are no li vestock feedstuffs assoc iated with the proposed uses of naphthalene acetates. At thi s time , the Age nc y has determined that NAA i s in Category 6(a)(3) (i.e., no reasonable ex pectation s o f finite residues of concern in meat and milk). Poult ry There are no poultry feed item s associated with th e currently re g is tered or proposed use s o f naphthalene acetates; thu s, a poultry feedi n g study is not required. Tol e rance s for the eggs and e dible tissu es of poultry nee d no t be establ i s hed. 

### 860 . 1500 C rop Fie ld Trials 4945100 t .der In pomegranate harves ted 45 da ys following the la s t of two applicatio n s of a 15. l % EC formulation ofNAA ethyl ester directed to the base of the tree as a 1% w/v a i sp ra y to run-off to pruned s prouts/ sucke rs , r es idu es of NAA were below th e LOQ (<0
. 05 ppm ) in/on all samples. Residue decline was not inve stigate d.

Page 8 of 11NAA Summary of Analytical Chemi srry and Re sid ue Data DP#: 0 423409

TABLE4. R es idu e D ata from Pomegranat e f i e l d Trial s with NAA. Location: City
. State: Zone Crop Matrix Total Rat e Pl II (days) Residues 2 ( ppm ) Year (Trial ID) 1 Varie t y (% w l v a i [average] so luti o n)'
Lo s t ll ill s . CA: 20 11 1 0 Wonderful Fruit 2X 1 % 45 <0.05. <0
. 05, <0.05. < 0.05 ( CA63 and CA64) ro.0 51 Gridley. CA: 2011 10 Wonderful Fruit 2 X 1% 45 <0.05, <0.05. <0.05. < 0.05 (CJ\65 a nd CA66) ro.0 51 1 Two app li ca ti ons of a I % so luti o n w e re made a t eac h tria l s ite
. 2 Re s idues ofNAA e th y l este r were determined b y a commo n moi ety me th od that conven s re s idue s ofNAA acetamide and NAA eth) I e s ter to AA
. The LOQ was 0.05 ppm. Values below the LOQ were not provided i n the ra w data . Tab le 5. Su mm ary of R es idu es from Pom eg ranate f i e ld Trial s wit h NAA et h y l ester. Commodity T ota l Rate 1 Ana l yte Pl II , n · ( % w l v ai ( days) s olution) Pome g ranate 2 

### x 1%**NAA ~**  45 2
1 Two appl i ca tion s of a I % so luti on were mad e at each trial s ite.**~** n = no . of indep enden t field trials. 3 Va lu e s based on total number of sample s . Resid ue Levels (ppm) Min
. 3 Max. 3 Ll\FT .i HAFT-I M e dian4
< 0.05 < 0.05 0.05 0.0 5 0.05 Mean 4 S D 0.05 N I I\

4 Value s based on per-trial averages . LAFT= lowest average field trip. H AFT = highes t average field trial. S D = s tandard deviati o n . For computation of the Ll\FT. I IAFT. median. mean. and s tandard deviation. values < LOQ arc assumed to be a t the LOQ
. N IA= Not app li cab l e. 5 Re s idue s ofNAA et hy l ester were det e rmined b y a common moi ety me th od that co nverts re s idues of NA/\ accta mid e and NAA eth y l e s ter to NAA
. 

### Co nclu s ions Th e s ubmitted pomegranate fi e ld trial data are adequate. The geographica l rep rese ntation o f field trial s are appropriate. In pomegranate h ar ves te d 45 days followin g the last of two application s of a 1 5.1 % EC formulation of NAA ethyl es t e r directed to th e base of th e tree as a I % w/ v ai sp ray to run- off (0.078 lb ae / gal 

### x 2 app lic ation s) to prun e d spro uts/ suckers , residues ofNAA were below the 

### LOQ ( <0
. 05 ppm) in/on a ll samp les. R esidue decline was not inv estiga t ed
. An acce ptable method was used for re sid u e quantitat io n , a nd adequat e s torage s tability data we r e sub mitted to s upport sampl e s torage dur a ti o n s and conditions for a ll a nalytes. 

### 860 .1 520 Processe d Food a nd Fee d There are no p rocesse d commodities associated with the p ro po sed u ses in the current petition 

### 860
. 1650 S ubmit ta l of A naly tical Refer e n ce S tandard s A s upply of NAA analytical s tandard i s n o t avai labl e in th e N ational Pest icid es S tandard s Repo s i tory. A n a ly ti cal s tand ard s mu s t b e s uppli ed. To date , the Repos itory h as n o t r ece ived a s uppl y ofNAA r efe re n ce s tan dard. As NAA i s th e ke y re s idue for e nforc eme nt , the petition e r is required to submit a 5-gram sampl e o f reference

Pa ge 9of11NAA Summary of Analytical Chemistry and Re sidue Dat a DP# : 0423409



### s tand ard a nd s upportin g documen tati on (s ee OCSPP Guid eli ne 860.1650) to the repository at th e add r ess below , to the att e nti on of either Th e resa Co le or Thuy Nguyen. Note that the full 9 -di g it ZIP code i s mandat ory o r the mail will be returned to the se nd e r . USE P A Nat io n a l P esticid e Stand ard s Re p os itory/ Ana lyti ca l Chemistry Branc h/OPP 70 1 Map es Road Fort George G. M e ade , M D 20755-5350 As a remind e r to th e petitioner , s uppli es of analytical standards must be rep le nish ed as requested by the reposi tory as lo ng as the tolerance is published in 40 CFR. 

### 860.1850/ 860.1900 Co nfined/ F ield Acc umul ation in Rot atio n a l Cro p s T here are no ro tati o nal crop data require m e nt s assoc iated with th e proposed u ses in the cu rrent pet iti o n. 

### 86 0 .155 0 Proposed To lera nc es To le ra nce s are estab li s hed und e r 40CF R § l 80. 1 55(a) for th e combin ed residu es of 1- naphth a le n eacetic ac id and its conj ugates calculate d as 1-naph thalen eacet ic acid from th e ap pli ca tion of 1-naphthal e nea ce tic acid, its a mmonium , so dium , o r pota ss ium s alt s, e th y l este r , a nd acetam id e. Th e established tolerances range fro m 0.05 ppm to 2.0 ppm . No Codex o r Canadian maximum residu e limit s ( MRL s) have b ee n establ i s hed for residues of (NAA), its sa lts , es t e r, and acetam id e for the use in thi s petition.

Tabl e 6 To lerance S ummar y for N AA Commod ity 

# I Es tablished/P roposed 

# I To leran ce (ppm ) R ecomme nd ed 

# I Co mm enlS; Corre ct Co111111odity To lerance ( ppm ) Definitio n 

### Tolerances Propo s ed U nder PP # 4E8310 Pom egranat e 

## I 0.05 

## I 0.05 

## I

Pa ge 10of 11NAA Summary of Analytical Chemistry and Re s idue Data DP# : 0423409


### Attachment l: 

### International Residue Lim its


### NAA (0560 0 2;) Summary of US and International Tolerances and Maximum Residue Limits Res idu e D efinition: 

## us Canada Mexico 2 Co dex 40 CF R 180.155: None None Pl ant: tolerance levels specified is to be determined by measuring onl y 1- naphth aleneace tic acid and its co njugates , calculated as th e Stoichiometric equ ivalent of I

- naphthaleneacetic acid Livestock: NA T o le ran ce (ppm) I MrLi:imum R es idu e limit (mg / kg) Comm od ity ' Mexico 2 

## us Canada Codex Pom egranat e 0.05 Comple t ed: M
. Negussie/ 05/ 05/ 15
1 Includes on l y commodities of interest for thi s action. Tolerance values s hould be the HED recommendations and not those propose d by th e applicant. 2 Mexico a dop t s US toleranc es and/o r Codex MRL s for it s export purpo ses.


### F. DO CU MENT TRACKING RDI: T. Morton 11 /1 8/15; E. R e ave s 11 /1 8 / 15 Petition Number: 4E8310 DP# : 423409 PC Code: 1 29032
Tc mpla1c Version Sc plc mbc r 2005



### Pa ge 11 of 11NAA [PC Code 056008] / lnterrc gio nal Research Project No. 4 [ IR-4] 

### B . 7.6 R esi du es Res ultin g fro m S up ervise d T ri al s (An n ex HA 6.3; A n nex III A 8 . 3) B.7.6.1 Res idu es i n Targe t C ro ps B.7.6.1. 1 Pomegra n ate Doc u me n t ID: MRID No. 4945 100 I PM RA No. Not Availab le 

### Report : B arney, W
. (2011) NAA: Magnitude of the Res id ue on Pomegranate. Project N umber : A5389. Unpub li shed study prepared by Interregiona l Researc h Project No. 4. 1 94 p. 

### G ui de li ne s: EPA OCS PP Hannonized Test Guideline 860 .1 500 Crop Fi e ld Trials (A ugus t 1996) PMRA Regulatory Directive DIR98-02

- Residue Chemistry Guidelines, Sectio n 9

- Crop Field Trials PMRA Regulatory Directive DIR2 0 I 0-05

- Revis ions to the Residue Che mi s try Crop Field Trial Requir e me nt s OECD Guide lin e 509 Crop Fi e ld Trial (September 2009) 

### GLP Co mp l i ance: No deviations from reg ulatory require me nts were report ed which wo uld h ave an impact on the validity of the study : 

### Acceptab ili ty: The study is considered scientifica ll y acceptable. The acceptability of this study for regulatory purposes is add ressed in the fo rth coming U.S. E PA Resid ue Che mi s try S umm ary D oc um e nt , DP# 423409. 

### Eva lu ator: Thurs ton G
. Morton , C hem i st Re g i stration Action Branch 4 Health Effects Divi sion ( H ED) (7509P)

Note: Thi s Data Evaluat ion Record (DE R) was originally prepared under contract by Versar. Inc. (6850 Versar Center, Springfield. VJ\ 22 151 ; submitted 2/ 2/15). The DE R has been reviewed by 1-1 ED and revised to reflect cu rrent Office of Pesticide Pro g r am s ( OPP ) policie s. 

### EXECUT I VE SUMMARY Th e Inte rr eg i o nal Research Pro j ect N umb er 4 ( IR-4 ) ha s s ubmitted field trial data for 1- naphthalen eacet ic acid (NAA) on pomegranate. Two field tri a ls we re conducted in th e U nited States during the 20 11 growing season in the North American Free Trade Agree m ent (NAFT A) Growing Zone 10 (CA). The above trial count reflects two pairs of trials con du c ted at the same locations that HED has detcnnined to be replicate trials. Each trial s ite co n s i sted of o ne untreated plot and o n e treated plot. At each trial location , the treated p lot r ece i ved two app li ca tion s of a 15. I % em ul s i fi ab l e co ncentra te (EC) fomrn l ation of NAA ethy l ester (Tre- Hold Sprout Inh ibitor A-112) directed to the base of th e tree as a I % w/ v ai spray to run-off to pruned sp routs/ suckers. The reported % dev iation from the target rate was S0.09. App lications were made at retreatment intervals of 60 days using ground equipment in
EPA MRID # : 4945 1 001 P age I of7NAA [PC Code 056008) / lnt erregional Research Proj ect No. 4 [IR-41
s pray vo lum es of 1 3 -23 gal/A
. No adjuvants were used. Sa mpl es of pomegranate s were harv ested at a preharvest interval ( PHI ) of 4 5 day s . All samples were maintained fro z en at the te s ting fac iliti es, duri ng shipping , and were stored frozen at the ana lyt ical laboratory until analysis
. The maximum storage inte rval for samples betwe e n harvest and extraction was 23 l days (7 .6 month s)
. Samples were analyzed within 5 da ys of extraction. Storage stab ilit y data generated concurrently w ith the fi e ld trial s tud y demon s trate that res idu es of NAA and NAA e thyl es ter , respectively , are stable in/on samples of pomegranate s tored frozen for up to 240 and 2 48 days (7.9 -8. 2 month s); no 0-day data were provid e d. T hese data are acceptab le to s upp o rt the s torage cond i tions and durations of sam ple s from the s ubmitted field trials ; however , storage stabi li ty s tudie s s hould alw ays include a 0-day s amplin g interva l t o establish th e residue leve ls prese nt at the time sample s are place d into s torage [see OPPTS 860. I 380(d)(6)( i) ]. Samp les were a nal yzed for re sidues of NAA using high performance liquid chromatography with fluore sce nce detecti o n ( HPLC/UV) adapted from Morse Laboratorie s , Inc
. analytical method NAA-AM-003. T he me thod is a common moiety method that co nve rt s residues ofNAA acetamide and NAA eth y l ester to NAA. The limit of qu a ntitation (LOQ ; de t e rmin ed a s the lowest lev e l o f me th od validat ion, LLMV) was 0
. 05 ppm. Acc e ptabl e method validation a nd concurrent recove ries were reported for samples of pome g ran ate fortified with NAA and NAA e thyl es ter at 0 .05

- 1 .0 ppm , thu s validati ng the me thod. The fortificati o n levels u se d in co ncurr ent method recovery were adequate to bracket expected residu e level s. Concurrent reco ve ries and re s idues in the treated sample s were not corrected for res idue s in contro l s . In pomegranate harves ted 45 da ys following the la s t of two application s of a 15.1 % EC fo rmul ation of NAA ethyl es ter direct e d to the base of the tree as a 1 % w / v ai spray to run-off to pruned s prout s/ suckers , re s idue s o f NAA we re b e low the LOQ ( < 0.05 ppm ) in/o n a ll samples. Residu e decline was not investi gated. I. 

### MATER IAL S AND 

### METHODS A. MATERIALS

Tab l e B
. 7
. 6. 1.1 -1. No me ncl at ure for NAA. Co mm o n n a m e NAA Identi ty 1 -naphthalcneacctic acid CAS no. 86-87-3 Compa ny experime nt a l name N I A Other sy non yms (if applicable) N I A 0 OH 

# I**~ ~** **~ ~** 
EPA MRIO # : 4945 1001 Page 2 of7NAA [P C Code 056008] / Int erre g ional Re search Project No. 4 [ IR -4] Table B .7 .6.1.1

- 1. Nom e n c l a ture f o r NAA. Co mm on nam e NJ\A ethyl ester Id ent i ty 1- Naplnhalcncacetic acid. ethyl es ter CAS no. 2122-70-5 Co mp a ny ex pe r im e n ta l nam e N I J\ Other sy n o n y m s ( i f a ppli cab le) N I A 0

### O~CH 3 

# I**~ ~** **~ ~**  Com m o n name NJ\J\ acc tamidc Id en ti ty 1-n aph thal e neace tamidc CAS n o. 86-86-2 Com p a n y expe ri m e n tal name N I A Other sy n o n y m s ( if app li cab le) N I A 0 NH 2 

# I**~ ~** **~ ~**  

### B . S tud y De s ig n 1. 

### Test Procedure Two field trials were conducted on pomegranate during the 201 1 growi ng season reflecting two applications of a 15.1 

### % EC fo rmulation ofNAA ethyl este r (T re-Hold Sp rou t Inhibitor A -11 2) directed to the base of the tree as a I % w/ v ai s pray to run-off to pruned sprouts/ s uckers. Field trial location s by NAFTA g rowi n g zone are s ummarized in Table B.7
. 6 .1.1- 2. The trial s se parated by < 20 mil es h ave been assesse d for ind e p e ndence as deta il e d in the tab le below. HED has determ in e d that each pair of trials constitutes a s in g l e trial wi th replicate s ample s for purposes of 860.1500 data requirements. Independ en t Trial Determination 1 T rial Nos. Differences Decision C l\63 & C J\64 Same l ocation and varietv Replicate *No other difference s in criteria CA6 5 & CA66 Same location and var i e tv Replicate 'No other differences in criteria 1 J\11 assessments are based o n th e replicate trial guidance presented in draft mem o 568
_ Cri tcria for Independence ofTri a l s 0 4 / 23 / 2013 (EPA and PMRA ).
EPA MRID # : 49451001 Pa ge 3 of7NAA [PC Co de 056008) / lnterr egio nal Researc h Project No
. 4 [ IR -4]

Ta b le B. 7 .6.1.1-2. Tria l N um ber s a n d Geographica l Locatio n s . Crop No. NAfTA Grow in g Zone Total Trials 1 2 3 4 5 6 7 8 9 10 11 12 Pomegranate Sub. 22 2 Req. 1 3 or 2 1 As per Table I of 860.1500 for pomegranate. three trials with a minimum of 6 sa mple s or two trial s with a minimum of 8 samples arc required. Geographic distribution is not specified for crops requirin g**3** trials: ho\\ ever. per Table 6 of 860.1500. Zone I 0 accounts for 99% of U.S. pomegranate production. 2 I JED has concluded that two pairs of the four Zone 10 tri als constitute si ngle tr i als with replicate samples for purposes of 860.1500 data requirement s. Locations and detailed u se patterns for the trials are provided in Table 

### B.7.6.1.1-3.
Tab le B.7
. 6
. 1.1 -3. St ud y Use P attern . Location: End-use Method of Appl ication / Timing of Vol um e Rate per Retrcatment Total Surfac tant/ City , State: Product' Application (gal /A) App li cation Interval Ratc2 Adjuvant Year (% ai (days) (% (Trial ID) so lution ) So l ution) Lo st Hills. 15
. 1% I. Directed to base of tree: blooming/ 13 I - 2x 1% None CA: 20 11 EC fruiting (CA63) 2
. Directed to base of tree: blooming 14 I 60 / fruiting Lost I li lls. 15
. 1 % I
. Directed to base of tree: blooming/ 16 I 

## -- 2x 1% one CA: 2011 EC fruiting (CJ\64) 2. Directed t o base of tree: blooming/ 1 5 I 60 fruiting Gridley. 15
. 1 % I
. Directed to base of tree: flowering/ 2 1 I 

## - - 2x 1 % None CJ\:20 11 EC bloom (C/\65) 2. Directed to base of tree: fruiting 22 1 60 Gridley. 15
. 1% I
. Directed to base of tree: flowering 23 1 

### -- 2x 1% None CJ\ : 20 11 EC 2
. Directed to base of tree: fruiting 22 I 60 (CJ\66) 1 1 5
. 1 % emul s iliablc concentrate EC fonnulation of NA/\ eth • I ester Tre

- Hold S rout Inhibitor A-11 2 ( ) ) p 2 Two app lication s of the I % solutio n were made at each tria l si t e . Pomegranates we re grow n and maint a ined acco rding to typical agricultural practices. Irr ig ation was u sed to s uppl ement ra infall at all trial s ites. No unusual weather cond iti ons were r eported to h ave adverse ly affecte d crop growth o r y ie ld s during the st ud y. Sa m p l e Ha n d li ng a nd P r e p a r at io n Sin g le co ntrol a nd dup li ca t e treated sampl es of p o me granate we re harv es ted fo llowin g application at a 45-day PHI. Samp les were placed in frozen storage at th e field sites w i thin



### - 3 .5 hours of h arvest and were s hipp ed w i thin 5- 14 days of harves t froze n on dry ice v ia FedEx to the analytical lab oratory , IR- 4 We s tern Region Satellite Labo rato ry (Honolu lu , HI ). At the a n alyti cal l abo rato ry, samp l es we re ho mo ge ni zed in the pre se nc e of dry ic e a nd were s to re d fro ze n 

### (

- -20 ° C) until extraction fo r analysis.

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### 2. Description of Analytical Procedures Samp les we re analyzed u s in g an HPLC / UY method adapted from Morse Lab o rato ries , Inc. Analytica l Method NAA-AM-003 entitled ··Reco mmended A n a l ytical Resid ue Method for 1- Naph thal e n eace ti c Acid , 1- Naphthaleneace tamid e , and/ or 1- Naphtha leneacetic Ac id Ethy l Este r , in Grape ( red and white), Grapefrui t, Tomato, and Green B e ll Pepper Matrice s". T he method i s a common moiety method that converts re s idues ofNAA acctam id e and NAA ethyl ester to NAA
. A comp lete descri ptio n of the meth od including a li st of minor modification s was included in the submission. Briefly , sample s were extracted by blending with distilled water. Residue s ofNAA ethyl ester were converted to NAA by base hydrolysi s w ith 50% NaO H at reflux for 3 hour s . The mixture was cooled and filtered , diluted with water, th e n partitioned w ith dichlorom e thane ( DCM). Th e resulting aqueous pha se was aci dified to pH < 2 with concentrated HCI and partitioned twice w i th DCM. The resulting organic pha ses were dried through sod ium su lfate, reduc ed by rotary evaporatio n , and adjusted to vo lume with D CM , then appl ied to a s ilica gel so lid pha se extractio n (SPE) column. Residues were e luted with DCM: I % acetic acid (99: I , v:v), and th e eluate was s ubj ec ted to so lv ent exchange wit h aceton itril e:wat e r ( 1: 1 , v :v). T he resu ltin g extract was filtered for ana lys is by HPLC/UV. The LOQ ( determined as the LLMV) was 0.05 ppm. We note that the petitioner a lso presented calculated values for the LOO and LOQ based o n the rec over ies obtained from samples fortified with NAA and NAA e th y l ester at the 0.05-ppm fortification leve l. The LOO for each matri x was calculated by multipl y in g the standard dev iation of recov e ry mea s urement s al the LLMV by the one-tailed t-stati s tic (confidence lev e l not re ported ) for s ix r e plicates , and th e LOQ was defined as 3x the LOO
. The ca lculated LOQs were 0.025 1 and 0.0285 ppm , respecti ve l y, for NAA and NAA ethyl ester ; correspo ndin g calculated LOD val ues were 0.008 35 and 0.00951 ppm. 

### II. RESUL TS AND DISCUSSION Method performance was eva lu ated durin g method va lid atio n and by u se of conc urrent recove r y samples. Pomegranate samp les were fortified with NAA and NAA e th yl ester at 0.050 -1. 0 ppm for method validation and 0. 10 ppm for concurrent reco veries. Recoveries were within the acceptable range of 70-120%; therefore, th e method was considered val id for th e analysis of NAA inion pomegranate (Tab le B.7.6 .1.1 -4). T he fort ifi cation leve l s bracketed the measured residues. Co ncurrent recove ri es were not co1Tected for apparent re s idues in con trols. The detector response was linear (coefficient of determination, 

### r2 =:: 0.9997) wi thin the range of 5- 50 ng/mL. Repr esentative chromatograms of con trol samples , fortified samp les, and treated sample s were provided. Th e control chromato g ram s generall y had n o peaks of interest abo ve the chromatograp hi c background. The fortified sample chromatograms co nt ai n e d o nl y the analyte of interest , and peaks were symmetr ical and we t I defined. Apparent r es idues in contro l s were below the LOQ (:S0.05 ppm). The rep orted residue values were not corrected for apparent residues in controls.

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T a b le 8 .7.6. 1.1

- 4
. S umm a r y o f M e th od Va l i d a t i o n a nd Co n c u r r e n t R ecove ri es o f N A A a nd NAA et h y l es t er fr o m P o m eg r a n a t e. Matrix 

# I Analyte 

# I Fortification 

# I Sample s ize 

# I Level (ppm) (n) M etho d Va lid a t io n 

### I NA/\ 

### I 0.050-1.0 

### I 12 

### I Pome gra nate 

### I I I NAA ethy l ester 

### I 0.050-1.0 12 Co n curre n t R ecovery 

### ) I NAA 

## I 0
. 1 0 

## I I 

## I I o me gra nate 

## I N 

### I 0. 1 0 

### I I 

### I AA et h yl ester 1 Recoveries were not cor rected for a ppa rent re s idu es in contro ls. 2 Standard dev iat i on is not calculated for s amp l e sizes < 3. R ecove rie s' 

# I Mean ± S td
. De v. 2

(% ) (%) 74-87 

### I 79 ± 4.6 73-90 

### I 83 ± 5.6

6 1 

## I 6 1 60 

### I 60


### Samp les w e re stored fro ze n for a maximum of 231 days (7.6 months ) from harve s t to extraction (Table B.7. 6. I
. l-5a )
. Sample s we re ana l yze d within 5 days of ex tracti o n. To s upp ort sample s torage durations, a concurrent s torage s tabi l ity study wa s co nducted with th e fie l d trial s tudy ; the re s ult s ar e presented in Tabl e B.7.6
. l.l- 5b. The data d e mon s trat e that re s idu es ofNAA and N AA e th y l es te r , r es pecti ve ly , are s tabl e in/on samp les of pomeg ranate stored fro ze n for up to 24 0 and 248 day s (7 .9-8. 2 month s); n o 0-day data we re pro v id ed. Th ese d ata are acceptab l e to s upp o rt the s torage co ndition s and duration s o f samples from the s ubmitted fi e ld trials ; howe ve r , s torage s tability s tudies s hou ld a lways inc lud e a 0-day samp li n g interval to establish th e res idu e levels present at the time s ampl es are pl aced into sto rage [see O CS PP 860.1380(d)(6)(i)).
Ta bl e 8. 7 .6. 1.1 -Sa
. Su mm ar y o f S t o r age Co nd itio n s . Matrix A nalytc Storage Actua l S t orage Interval o f Dem o n s trated S torag e S tability ( RA C or Extract) Temperature Duration 1 ( OC) (day s/month s) Po megra nate Nl\A

- -20 224-23 1 days Re s idu es of NA/\ and NA/\ ethyl es ter arc (7.4

- 7.6 months) s table inion sample s of pomegranate stored AA e th yl este r frozen for 240 day s (7.9 months) and 248 day s ( 8.2 month s)
. re spect i ve l y. 2 1 Interval from harvest lo ex tra ction. Samples were analy..:cd within 3

- 5 da) s of extrac11on. 2 Based on concurrent storage stab ilit y st ud y. See Tab le B .7.6. 1
. 1-5b
T ab l e B
. 7
. 6. 1.1 -S b
. S t a b il it y of N A A a nd NAA e t h y l es t er in F r oze n P o m eg r a n a t e. Analytc Spi ke Sto rage Fresh Fortifi ca ti o n Sto red Sample Mean Corrected % Level interval Recoveries (%) Recoverie s (%) Rec overy (%) recovery 1 (pp m) ( days) NA/\ 0. 10 240 79 73. 73. 74 73 92.8 NAA ethyl ester 0. 1 0 248 8 1 81.76.74 77 95. 1 1 Co rrec ted for reco ve ry in fres hl y fortified sa mpl es. 

### The res ults from the subm itted field tria ls are pre se nted in T ab les B.7.6.1. 1

- 6 and B.7
. 6.1.1

- 7. In pomegranate harv es ted 45 da ys fo ll owi ng th e last of t wo ap pli cat ions of a 1 5 .1 % E C formulation ofNAA ethyl ester directe d to the ba se of the tree as a 1 % w/ v ai spray to run-off to prun e d s prout s/s ucke rs , res idue s ofNAA were belo w th e LOQ (< 0.05 ppm ) i nio n a ll sam ples. Res idu e decline was not inves ti ga ted.

EPA MRID # : 4945 1 00 1 Pa ge 6 of7NAA [ PC Co de 0 560 08]/lnterr eg io na l R esearc h Project No
. 4 [ IR -4 ]
TABL E 8 .7.6.1.1-6. R es id u e Data fr o m P o m eg ranat e Fie l d Tri a l s wit h N AA. Location: City. State: Zone Crop Matrix Total R ate Pl II (days) Rcsiducs 2 (p pm ) Year (Trial 10 ) 1 Variety (% So lution) 1 la verage]

Lost I lill s. CA: 201 I 10 Wonderful Frui t 2X 1 % 4 5 < 0.05. < 0.05. < 0.05. <0.05 (CA63 and**CA6 )**  [< 0.0 5) Gridley. CA : 201 I 10 Wonderful Fru it 2X 1% 4 5 <0.0 5. < 0.05. <0.05. <0.05 (CA65 a n d CA66) f < 0
. 05) 1 Two applica ti o n s of a I % so luti o n were made at eac h t rial s ite
. 2 R esid ue s ofNAA et h y l ester were determined b y a common moiety meth o d that convert s re s idues ofNAA aee tamide and NAA eth)I ester to AA. TI1c LOQ was 0.05 ppm . Values below the LOQ were not pro vided in the raw data.
Ta bl e 8 .7.6 .1.1 -7. S ummar y o f R es idue s fr o m Pom eg ra n ate Fi e ld T r ia l s wit h NAA et h y l es ter. Com modity T o ta l Rat e 1 Analyte PHI n2 (%So lution ) (days) Pomegrana te 2X 1 % AA 5 45 2 1Two r 1pplication s of a I % s olution were mad e a t eac h tri a l s it e. 2 n = no. of lield tri a l s. 1 Values based on total number of sa mple s. Re s idu e Levels ( ppm) Min
. 1 Max. 3 LAFT'' HAf1'4 Median • Mean 4 SD <0.0 5 <0.0 5 < 0.05 < 0.0 5 0.05 0.05 NIA

4 Values based on per-trial averages. LAFT= lowest average licld trip
. I IA FT = highe s t average lield tri al. S D = standard deviation. For computation of th e LAFr. H AFT. median. mean. and sta ndard de viat ion. values < LOQ arc ass umed to be at the L OQ. N IA= Not applicable. 5 R esid ues ofNAA et hy l este r we r e determ i ned b y a commo n moi.:ty me th od that conver t s re s idues ofNAA ace tamide and NAA e th y l ester to NAA. 

### III. CONCLUS IO NS The pomegranate field trial s a r e considered sc ientifically acce pt ab le. In pom egranate harvested 45 day s following the last of two applicati o n s of a 15.1 

### % EC formu latio n of NAA e thy l e s t e r direc ted to the ba se o f the tree as a I % w/ v ai spray to run- off to pruned sprout s/s uckers , r es idu es of NAA were bel ow the LOQ (<0 .05 ppm ) in/o n all samp les . R es idu e decline was not in ves tigated
. An acceptab le m e thod was u sed for residu e quant itation , a nd adequate s tora ge s tab ilit y d ata were s ubmitted to support samp le s torage durations a nd cond i tio n s fo r a ll anal ytes. 

### I V
. REFERE NCES None.

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