NAA Summary of Analytical Chemistry and Residue Data DP#: D399621



### Page 1 of 16 **UNITED STA**

**TES ENVIRONMENTA L PROTECTION A** **GENCY WA** **SHINGTON, D.C. 20460** OFFICE OF CHEMICAL SAFETY AND POLLUTION PREVENTION



### MEMORANDUM **Date:** October 3, 2012 **SUBJECT:** 1 -Naphthaleneacetic acid (NAA), its salts, ester, and acetamide . Expan sions of

Existing Crop Group/Representative Commodity Uses to Fruit, Pome, Group 11 - 10 and New Uses in/on Avocado, Mango, Mamey Sapote, and Rambuttan. **Summary of Analytical Chemistry and Residue Data. PC Code:**  056002 **DP Barcode:** 399621 **Decision No.:** 461439 **Registration Nos. :**  5481 - 429 and 5481 - 541 **Petition No.:** 2E7991 **Regulatory Action:** Amended Section 3 **Risk Assessment Type:** NA **Case No.:** 0379 **T XR No.:**  NA **CAS No.:** 86 - 87 - 3 **MRID Nos.:** 48749901 and 02 **40 CFR:** 180.155 

### FROM: Gary

Otakie, Chemist Risk Assessment Branch 4 Health Effects Division (7509P) **THROUGH:** Susan V. Hummel, S enior Scientist

Elissa Reaves, PhD., Branch Chief Risk Assessment Branch 4 Health Effects Division (7509P) **TO:** Thurston Morton , Risk Assessor

Risk Assessment Branch 4 Health Effects Division (7509P) And Laura Nollen/Barbara Madden Risk Integration, Minor Use & Emergency Response Branch Registration Division (7505P)NAA Summary of Analytical Chemistry and Residue Data DP#: D399621



### Page 2 of 16 **Action Requested** Under PP#2E7991, The Interregional Research Project Number 4 (IR - 4) has submitted a petition for the establishment of permanent tolerances for residues of the plant growth regulator 1 - Naphthaleneacetic acid (NAA ) in conjunction with requests for amended Section 3 registrat ions of the two pesticide formulations: TRE - HOLD Sprout Inhibitor A112, and Fruitone N. The petitioner is proposing the establishment of the following permanent tolerances for residues of NAA: Avocado..... ................................ ................................ .............. 0.05 ppm

Mango ................................ ................................ ....................... 0.05 ppm Mamey Sapote ........................................... 0.05 ppm Rambuttan ................ ........................................... 3.0 ppm Fruit, pome, group 11 - 10 ................................ ............. .........0.15 ppm **Discussion** 1 - Naphthaleneacetic acid (NAA), its salts, ester, and acetamide are plant growth regulators (PGR) which are collectively referre d to as naphthalene acetates. The PGR activity of NAA is due to its structural similarity to the natural plant hormone indole acetic acid (IAA). They are currently registered for use on various orchard and fruit crops to prevent preharvest drop of fruits, thin fruit trees, and delay

flower induction. They

can also stimulate growth and delay leaf drop on ornamentals. New residue chemistry

data on avocado and rambuttan were submitted to support these uses, except for the Fruit, pome, group 11 - 10, which is an expansion of the current crop group tolerance on “Fruit, pome, group 10”, and relies on existing residue data. Residues of NAA were below the LOQ (<0.05 ppm) in/on avocado harvested 9 - 11 days following either one or two paintbrush or sponge application s of a 1.27 - 1.30% ai solution of the 15.1% EC formulation of NAA ethyl ester. Following one foliar directed application of the 3.5% SC formulation of NAA sodium salt at 90 and 900 ppm (i.e. 1X and 10X), respectively , residues (and per trial averages) of NAA in/on rambutan fruit harvested at a 2 - day PHIwere 0.0786 - 0.636 (0.108 - 0.621) and 1.25 - 5.06 (1.35 - 4.95) ppm. There are an adequate number of avocado and rambuttan field **trials** with acceptable field trial data from representative geographical locat ions. A tolerance level of 0.15 ppm, for Fruit, pome, group 11 - 10 is appropriate to cover the use of NAA on the Fruit group 11. The Organisation for Economic and Co - operation Development (OECD) Tolerance Estimation Procedures were used to determine app ropriate tolerance levels for Rambuttan, while for avocado the tolerance is based of the level of quantitation (0.05 ppm).NAA Summary of Analytical Chemistry and Residue Data DP#: D399621



### Page 3 of 16 A tolerance of 2.0 ppm rather than 3.0 ppm is required for rambuttan. **Note that this tolerance level is different than that proposed**  **by the petitioner who used NAFTA tolerance estimation procedures.**  Tolerances are established under 40CFR§180.155(a) for the combined residues of 1 - naphthaleneacetic acid and its conjugates calculated as 1 - naphthaleneacetic acid from the application of 1 - naphthaleneacetic acid, its ammonium, sodium, or potassium salts, ethy l ester, and acetamide in/on sweet cherry , fruit pome group 11, olive, orange, pineapple, and tangerine. A time - limited tolerance under 40CFR§180.155(b) is also established for avocad o (expires 12/31/12) in connection with a Section 18 emergency exemption . The established tolerances range from 0.05 ppm to 0.15 ppm. The current tolerance expression for NAA is not in accord with our current guidance. See Conclusion below for appropri ate wording. **Conclusion** 1 Inbrief, a revised Section F proposing a tolerance of 2.0 ppm for NAA in/on Rambuttan is required. HED has examined the residue chemistry database for NAA.. With regards to NAA for PP#2E7991, pending submission and revised Sections B and F (see requirements under Recommended L abel Changes and Tolerance Recommendations), there are no residue chemistry issues that would preclude granting amended registrations for amended Section 3 registrations of six pesticide formulations: containing NAA for use on a variety of crops, and to expand currently registered foliar uses or es tablishment of tolerances for residues of NAA only in/on the following commodities:

Avocado..... ................................ ................................ .............. 0.05 ppm Mango ................................ ................................ ....................... 0.05 ppm Mamey Sapo te ........................................... 0.05 ppm Rambuttan ................ ........................................... 2.0 ppm Fruit, pome, group 11 - 10 ................................ .............. .........0.15 ppm The amended registrations are limited to expansions to add the commodities specified under the new crop groups/subgroups and Avoc ado, Mango, Mamey Sapote, Rambuttan and do not include substantive changes to currently registered use patterns (i.e., maximum use rates, retreatment intervals, preharvest intervals, use of adjuvants, etc.). **Tolerance Recommendations** A revised Section F is needed, proposing tolerances as follows:NAA Summary of Analytical Chemistry and Residue Data DP#: D399621



### Page 4 of 16 Avocado..... ................................ ................................ .............. 0.05 ppm Mango ................................ ................................ ....................... 0.05 ppm Mamey Sapote ........................................... 0.05 ppm Rambuttan ................ ........................................... 2.0 ppm Fruit, pome, group 11 - 10 ................................ .............. .........0.15 ppm **The current tolerance expression fo r NAA is not in accord with our current guidance. The**  **tolerance expression should read: Tolerances are established**  **for the combined residues of 1 -**  **naphthaleneacetic acid, including its metabolites and degradates**  **in/on avocado at 0.05 ppm, mango at 0.05 pp m, Mamey**  **Sapote at 0.05 ppm, Rambuttan at 2.0 ppm, and Fruit, pome, group 11 at 0.15 ppm. Compliance with the tolerance levels specified is to be determined by measuring only**  **1 -**  **naphthaleneacetic acid and its conjugates, calculated as the Stoichiometric equivalent of 1**  **- naphthaleneacetic acid, in or on the commodity.**  **Recommended Label Changes** . The Fruitone Llabel must have a pounds per gallon statement. Aerial application must be made in a minimum of 10 gallons/acre. A human health risk assessment is forthcoming. **Note to PM:** *** Use information was taken from Section B of the petition. Only use information for the proposed new uses on Avocado, Mango, Mamey Sapote and Rambuttan were reviewed. HED**  **has not checked the labels to ensure that use directi ons for currently registered uses have not**  **been revised. The PM must ensure that the use directions for the remaining commodities have not changed since any changes required in the RED were made.**  Tolerances should be revised, as needed, to reflect the co rrect commodity definitions as specified in Table 10. A human heath risk assessment is forthcoming.NAA Summary of Analytical Chemistry and Residue Data DP#: D399621



### Page 5 of 16 **Background** The chemical structure and nomenclature of - Naphthaleneacetic acid (NAA), its salts, ester, and acetamide and the physicochemical properti es are presented in Tables 1 and 2. **Table 1. NAA Nom enclature**  Chemical structure O N H 2 O O H

Common name NAA acetamide NAA Molecular Formula C 12 H 11 NO C 12 H 10 O 2 Molecular Weight 185.23 186.20 IUPAC name 2 - (1 - naphthyl)acetamide 2 - (1 - naphthyl)acetic acid CAS name 1 - naphthaleneacetamide 1 - naphthaleneacetic acid CAS # 86 - 86 - 2 86 - 87 - 3 PC Code 056001 056002 Chemical structure 

### O O K + 

### O O N H 4 +

Common name NAA potassium salt NAA ammonium salt Molecular Formula C 12 H 10 O 2 K C 12 H 13 NO 2 Molecular Weight 224.31 203.24 IUPAC name potassium - 2(1naphthyl)acetate ammonium - 2(1naphthyl)acetate CAS name 1 - naphthalnene acetic acid, potassium salt 1 - naphthaleneacetic acid , ammonium salt CAS # 15165 - 79 - 4 25545 - 89 - 5 PC Code 056003 056004NAA Summary of Analytical Chemistry and Residue Data DP#: D399621



### Page 6 of 16 **Table 1. NAA Nom enclature**  Chemical structure 

### O O Na + 

### O O C H 3

Common name NAA sodium salt NAA ethyl ester Molecular Formula C 12 H 10 O 2Na C 14 H 14 O 2 Molecular Weight 20 8.2 214.26 IUPAC name sodium - 2(1naphthyl)acetate ethyl - 2(1naphthyl)acetate CAS name 1 - Naphthaleneacetic acid, sodium salt 1 - Naphthaleneacetic acid, ethyl ester CAS # 61 - 31 - 4 2122 - 70 - 5 PC Code 056007 056008 **Table 2. Physicochem ical Properties of NAA**  **1 Param**  **eter Value**  **Reference** Active Ingredient **NAA acetam ide**  Melting point/range 182 - 184 C Farm Chemicals Handbook pH of 1% aqueous suspension 5.1 Product CSF Density or specific gravity 0.221 g/cm3 Product CSF Water solubility (20 C) not available Solvent solubility (20 C) not available Vapor pressure at 20 C not available Dissociation constant (pKa) not available Octanol/water partition coefficient (Kow ) not available UV/vis absorption spectrum not available Active ingredient **NAA** Meltin g point/range 130 C Farm Chemicals Handbook pH of 1% aqueous suspension 3.45 RD D265117, 5/15/00, B. Kitchens Density or specific gravity 0.45 g/mL CB Nos. 3468 and 3469, 6/3/88, F. Suhre Water solubility (20 C) 0.042 g/100 mL CB Nos. 3468 and 3469, 6/ 3/88, F. Suhre Solvent solubility (20 C) xylene 5.5 g/100 mL CCl 4 1.06 g/100 mL freely soluble in acetone, ether, and chloroform CB Nos. 3468 and 3469, 6/3/88, F. Suhre Farm Chemicals Handbook Vapor pressure at 20 C 0.3 mm Hg at 26 C CB Nos. 3468 and 34 69, 6/3/88, F. Suhre Dissociation constant (pKa) 3.16 x 10 - 4 CB Nos. 3970 and 3971, 7/5/88, F. Suhre Octanol/water partition coefficient (Kow ) not applicable; polar compound UV/vis absorption spectrum not available Active ingredient **NAA sodium salt**  Melting point/range >300 C CB Nos. 3468 and 3469, 6/3/88, F. SuhreNAA Summary of Analytical Chemistry and Residue Data DP#: D399621



### Page 7 of 16 **Table 2. Physicochem ical Properties of NAA**  **1 Param**  **eter Value**  **Reference** pH of 1% aqueous suspension 9.1 CB Nos. 3468 and 3469, 6/3/88, F. Suhre Density or specific gravity 0.46 g/mL CB Nos. 3468 and 3469, 6/3/88, F. Suhre Water solubility (20 C) 340 g/100 mL CB Nos. 3468 and 3469, 6/3/88, F. Suhre Solvent solubility (20 C) insoluble in nonpolar solvents CB Nos. 3468 and 3469, 6/3/88, F. Suhre Vapor pressure at 20 C not available Dissociation constant (pKa) 3.16 x 10 - 4 CB Nos. 3970 and 3971, 7/5/88, F. S uhre Octanol/water partition coefficient (Kow ) not applicable; polar compound UV/vis absorption spectrum not available Active ingredient **NAA ethyl ester** Boiling point/range >150 C Old unreviewed Union Carbide data pH of 1% aqueous suspension not av ailable Density or specific gravity 1.11 at 20 C Old unreviewed Union Carbide data Water solubility (20 C) insoluble Old unreviewed Union Carbide data Solvent solubility (20 C) soluble in xylene, toluene, ethanol, acetone, and methyl ethyl ketone Old unreviewed Union Carbide data Vapor pressure at 20 C not available Dissociation constant (pKa) not available Octanol/water partition coefficient (Kow ) not available UV/vis absorption spectrum not available 1 No physicochemical properties information was available concerning the NAA potassium and ammonium salts.NAA Summary of Analytical Chemistry and Residue Data DP#: D399621



### Page 8 of 16 **860.1200 Directions for Use**  The petitioner has submitted copies of the proposed labels for Tre - Hold Sprout Inhibitor A - 112 and Fruitone L. Tre - Hold Sprout Inhibitor A - 112 is a soluble concentrat e formulation containing 15.1% NAA, ethyl ester (1 lb/gal NAA). Fruitone L is a soluble concentrate formulation containing 3.5% NAA, sodium salt. The pounds per gallon statement is missing. The proposed use directions are presented in Table 3 below. **Ta ble 3. Sum**  **ma ry of Directions for Use of NAA, potassium** **and sodium salts**  Applic. Timing, Ty pe, and Equip. Formulation Applic. Rate (lb ae/A) Max. No.

Applic. per Season Max.

Seasonal Applic. Rate (lb ai/A) PHI

(days) Avocado, Mango, and Mamey Sapote F oliar spray/ brush/sponge/ paint roller TRE - Hold Sprout Inhibitor A 112, EPA Reg. No. 5481 - 429; 15.1 % NAA, ethyl ester (1 lb/ gal) 0.0 78 lb ae/gal

11 oz. product/gallon (1.1% w /w) two per

year 10 days Use Directions and Limitations: Prune and tre at pruned branches and limbs within a few days. Apply an average of 3 fluid ounces mixture per tree. A minimum 45 - day RTI is specified. The REI is 12 hours. Rambutan Foliar spray Fruitone L, EPA Reg No.

5481 - 541 (3.1 % NAA) 90 ppm solution one per year 2 days Use Directions and Limitations: Spray Rambuttan panicles to runoff. The REI is 12 hours. Fruit, Pome, Group 11 - 10 For chemical thinning: Foliar spray, Aerial Fruitone L, EPA Reg No.

5481 - 541 (3.1 % NAA) 0.5 to 4.0 fl oz/100 gal NS NS Fr uit set Use Directions and Limitations: Apply at petal fall and/or early fruit set. Ensure uniform spray coverage using tree row volume. For ground applications use up to 500 gal water per acre. For aerial applications, use 5 - 10 gallons of water per acre. Directions provided for apples and pears. For other fruits in crop group, follow directions for thinning. To control pre harvest drop: Foliar spray, Aerial Fruitone L, EPA Reg No.

5481 - 541 (3.1 % NAA) 0.11 NS 150 g/A 2 days Use Directions and L imitations: Use sufficient water to ensure coverage, by air a minimum of 5 gallons. A typical application is 8 - 32 fl oz per acre, made 1 - 4 weeks prior to harvest. If needed, repeat at weekly intervals. Directions provided for apples and pears. 

### Conclusion. The proposed use directions are adequate to allow evaluation of the residue data relative to the proposed uses. The Fruitone L label must have a pounds per gallon statement. Aerial application must be made in a minimum of 10 gallons/acre.NAA Summary of Analytical Chemistry and Residue Data DP#: D399621



### Page 9 of 16 **860.13 00 Nature of the Residue**  **– Plants**  RED Residue Chemistry Chapter D299296, 10 MARCH 2004, G. Otakie 

### Acceptable apple and olive metabolism studies have been previously submitted and reviewed. Based on the nature of residues identified from the apple and ol ive metabolism studies, HED has previously

determined that the terminal residues of concern in plants are the parent compounds, NAA and its conjugates and that the qualitative nature of the residues in plants (i.e., orchard trees) is adequately

understood. For purposes of the current petition the nature of the residue in plants is adequately

understood. **860.1300 Nature of the Residue -**  **Livestock** RED Residue Chemistry Chapter D299296, 10 MARCH 2004, G. Otakie 

### An acceptable goat metabolism study has bee n previously

submitted and reviewed. Based on these data, HED has previously concluded that the qualitative nature of the residue in ruminants is adequately

understood . The terminal residues of concern in ruminants are the parent compounds, NAA and its co njugates. The available ruminant metabolism data are adequate to support the proposed uses. There are no poultry feed items associated with currently registered or proposed food uses of NAA; thus a poultry metabolism study

is not required. **860.1340 Res idue Analytical Methods**  RED Residue Chemistry Chapter D299296, 10 MARCH 2004, G. Otakie 

### Enforcement and data collection methods: The residue analy tical methods, currently

listed in Volume I I of the Pesticide Analy tical Methods, are inadequate for the enf orcement of tolerances for residues of a - naphthaleneacetic acid (Pesticide Reg. Sec. 180.155) and a naphthaleneacetamide (Pesticide Reg. Sec. 180.309) in/on plant commodities because these methods use benzene, a hazardous or toxic reagent. An HPL C method using fluorescence detection (Method NAA - AM - 001) for apples and peas and a similar method for olives and olive oil (Method NAA - AM - 002) has been previously submitted for determination of NAA in plant commodities. These methods include extraction with water and incorporate a basic hydrolysis step to release bound residues. These methods do not use benzene or diazomethane which are being discouraged by the Agency

for safety

reasons. Theses methods have been subjected to successful independent laboratory valid ations. Acceptable recoveries were obtained from apples, olives and olive oil fortified with NAA at the method LOQ (0.01 ppm) and at 1.0 ppm. This method is suitable for enforcement.NAA Summary of Analytical Chemistry and Residue Data DP#: D399621



### Page 10 of 16 Avocado samples were analy zed using an HPL C/UV method adapted from Mor se Laboratories, In c. Analy

tical Method NAA - AM - 003 entitled “Recommended Analy tical Residue Method for 1 - Naphthaleneacetic Acid, 1 - Naphthaleneacetamide, and/or 1 - Naphthaleneacetic Acid Ethyl Ester, in Grape (red and white), Grapefruit, Tomato, and Green B ell Pepper Matrices”. The method is a common moiety method that converts residues of NAA acetamide and NAA ethyl ester to NAA. A number of minor modifications to the method were specified including changes in clean - up procedures, reagents, and sample siz es. Rambutan samples were analy zed using an HPL C method adapted from Morse L aboratories, Inc. Analy tical Method NAA - AM - 003 entitled “Recommended Analy tical Residue Method for 1 - Naphthaleneacetic Acid, 1 Naphthaleneacetamide, and/or 1 -Naphthaleneacetic A cid Ethyl Ester, in Grape (red and white), Grapefruit, Tomato, and Green Bell Pepper Matrices”. The method is a common moiety

method that converts residues of NAA acetamide and NAA ethyl ester to NAA. A number of minor modifications to the method were sp ecified including changes in clean - up procedures, reagents, and sample sizes. **860.1360 Multiresidue Methods** D232463, D294854, 30 OCT 2003, G. Otakie 

### Multiresidue method (MRM) data have been submitted previously in support of the registration of NAA, i ts salts, ester and acetamide. Naphthaleneacetamide was found to chromatograph satisfactorily

using Pesticide Analy

tical Manual (PAM) Vol. I , Section 302 DG 5. Naphthaleneacetamide was found to produce a 50% full scale deflection (FSD) with a 50 nanogram injection and the relative retention time to chlorpy rifos is approximately

0.8. Average recoveries for naphthaleneacetamide spiked into pears at approximately 0.1 ppm and 1.0 ppm were 97.8 and 104%, respectively , for Section 302, method E1, without Floris il cleanup. Apple spikes using this procedure could not be quantified due to interference in the apple matrix. Naphthaleneacetamide was found not to be recoverable through Florisil, so it would not be recoverable through Protocols E or F. Therefore, testi ng under PAM Vol. IProtocol E, for apples and pears, and Protocol F, for olives, was suspended prior to recovery experiments through the entire Sections 303 and 304 methods. FDA MRM’s are not suitable as enforcement methods for NAA. **860.1380 Storage Sta bility**  RED Residue Chemistry Chapter D299296, 10 MARCH 2004, G. Otakie 

### Adequate storage stability data have been submitted 

## and reviewed for apples, pears, and olives. These data indicate that residues of 1 - naphthaleneacetic acid are reasonably stable und er frozen storage conditions in/on the above commodities for up to 

## 12 months. The current submission included storage stability data which showed NAA and NAA ethyl ester stored in frozen avocado were stable for up to 27 months and stored in frozen Rambuttan stable up to 25 months. The storage stabilty data adequately

support the storage conditions and samples collected from the avocado and Rambuttan field trials.NAA Summary of Analytical Chemistry and Residue Data DP#: D399621



### Page 11 of 16 **860.1400 Water, Fish, and Irrigated Crops** There are no proposed uses that are relevant to this guideline topic. **860.1460 Food Handling** There are no proposed uses that are relevant to this guideline topic. **860.1480 Meat, Milk, Poultry, and Eggs** RED Residue Chemistry Chapter D299296, 10 MARCH 2004, G. Otakie 

### Li vestock There are no livestoc k feedstuffs associated with the current new proposed uses. At this time, the Agency has determined that 

## NAA is in Category 6(a)(3) (i.e., no reasonable expectations of finite residues of concern in meat and milk). Poultry There are no 

## poultry feed ite ms associated with the currently registered or proposed food/feed uses of naphthalene acetates; thus, a poultry feeding study

is not required. Tolerances for the eggs and edible tissues of poultry need not be 

## established. **860.1500 Crop Field Trials** 48749 901.der Avocado 

### Residue data from the avocado crop field trials are reported in Table 1. A summary of the residue data is presented in Table 2. Residues of NAA were below the LOQ (<0.05 ppm) in/on avocado harvested 9 - 11 days following either one or two paintbrush or sponge applications of a 1.27 - 1.30% ai solution of the 15.1% EC formulation of NAA ethyl ester. Applications made to cut surface and surrounding branches. Samples were harvested from each plot at a 2 - day PHI . Inthe residue decline trial, r esidues of NAA in/on avocado were below the LOQ at all PHI s; therefore, residue decline could not be assessed.NAA Summary of Analytical Chemistry and Residue Data DP#: D399621



### Page 12 of 16 **TABLE 6 Residue Data from** **Avocado Field Trials with NAA ethyl ester.** Trial ID (City, State; Year) 1 Zone Avocado Variety Commodity Total Rate (% solution) PHI

(days) NAA Residues 2 [Average] Homestead, FL; 2006 ( - FL41) 3 Lula Fruit 1 x 1.27% 10 <0.050, <0.050 [<0.050] 2 x 1.27% 11 <0.050, <0.050 [<0.050] Exeter, CA; 2006 ( - CA95) 10 Zutano Fruit 1 x 1.27% 10 <0.050, <0.050 [<0.050] 2 x 1.27% 9 <0.050, <0.050 [<0.050] Irvine, CA; 2006 ( - CA96, - CA97, **and** - CA98) **[Target PHI]** 10 Hass Fruit 1 x 1.28 - 1.30% 10 - 11 <0.050, <0.050, <0.050, <0.050, <0.050, <0.050 [<0.050] 2 x 1.28 - 1.30% 10 <0.050, <0.050, <0.050, <0.050, <0.050, <0.050 [<0 .050] Irvine, CA; 2006 ( - CA96) **[Additional Decline PHIs]**  10 Hass Fruit 1 x 1.30% 1 <0.050, <0.050 [<0.050] 7 <0.050, <0.050 [<0.050] 15 <0.050, <0.050 [<0.050] 21 <0.050, <0.050 [<0.050] 2 x 1.30% 1 <0.050, <0.050 [<0.050]

6 <0.050, <0.050 [<0.050] 14 <0.050, <0.050 [<0.050] 21 <0.050, <0.050 [<0.050] 1 HED has concluded that trials - CA96/ - CA97/ - CA98 constitute a single trial with replicate samples for purposes of 860.1500 data requirements. 2 A total of two a

pplications of solution were made at each trial site, with samples collected after each application. 3 Residues of NAA ethyl ester were determined by a common moiety method that converts residues of NAA acetamide and NAA ethyl ester to NAA. The LOQ was 0 .05 ppm. **TABLE 7 Sum ma**  **ry of Residue Data from Avocado Field Trials with NAA ethyl ester.**  Commodity Analyte Total Rate (% solution) PHI (days) Residue Levels (ppm) 1 n Sample Min. Sample Max. LAFT 2 HAFT 2 Median Mean Std. Dev. Avocado, Fruit NAA 3 2 x 1.28 - 1.30% 10 - 11 3 <0.05 <0.05 <0.05 <0.05 0.05 0.05 N/A 2 x 1.28 - 1.30% 9 - 11 3 <0.05 <0.05 <0.05 <0.05 0.05 0.05 N/A 1 Except for sample min/max, values reflect per trial averages; n = no. of field trials. N/A = not applicable. 2 LAFT = lowes t average field trial; HAFT = highest average field trial. 3 Residues of NAA ethyl ester were determined by a common moiety method that converts residues of NAA acetamide and NAA ethyl ester to NAA. 

### An issue was raised about the separation distance fo r the avocado field trials. The petitioner indicated that since the study

was conducted in 2006, the trial separation guidance developed for 2012 studies was not achievable because of the unique application method used in the study .NAA Summary of Analytical Chemistry and Residue Data DP#: D399621



### Page 13 of 16 Conclusions The subm itted avocado field trial data are adequate. Residues of NAA were below the LOQ (<0.05 ppm) in/on avocado harvested 9 - 11 days following either one or two paintbrush or sponge applications of a 1.27 - 1.30% ai solution of the 15.1% EC formulation of NAA ethylester. In the residue decline trial, residues of NAA in/on avocado were below the L OQ at all PHI s; therefore, residue decline could not be assessed. An acceptable method was used for residue quantitation, and adequate data were submitted to support sample storage intervals and conditions. 48749902.der Rambuttan 

### Residue data from the rambutan field trials are reported in Table 3. A summary of the residue data are presented in Table 4. Following one foliar directed application of the 3.5% SC formu lation of NAA sodium salt at 90 and 900 ppm, (i.e. 1X and 10X) sprayed to runoff respectively , residues (and per trial averages) of NAA in/on rambutan fruit harvested at a 2 - day PHIwere 0.0786 - 0.636 (0.108 - 0.621) and 1.25 - 5.06 (1.35 - 4.95) ppm. Residue decline data were not submitted and are not needed for crops requiring three or fewer trials. **TABLE 8 Residue Data from** **Ram butan Field Trials with NAA sodium** **salt.** Trial ID (City, State; Year) Zone Rambutan Variety Commodity Total Rate (ppm) PHI

(days) NAA Residues 1 [Average] Kurtistown, HI; 2007 ( - HI08) 13 Jit Lee Fruit 90 2 0.0786, 0.137 [0.108] 900 2 1.25, 1.44 [1.35] Pepeekeo, HI; 2007 ( - HI09) 13 Jit Lee Fruit 90 2 0.605, 0.636 [0.621] 900 2 4.83, 5.06 [4.95] 1 Residues were determined by a common moiety method that converts residues of NAA acetamide and NAA ethyl ester to NAA. Per trial averages were calculated by the study reviewer. **TABLE 9 Sum ma**  **ry of Residue Data from Ram** **butan Field Trials with NAA sodium salt.**  Commodity Ana lyte Total Rate (ppm) PHI

(days) Residue Levels (ppm) 1

n Sample Min. Sample Max. LAFT 2 HAFT 2 Median Mean Std. Dev. Rambutan, Fruit NAA 3 90 2 2 0.0786 0.636 0.108 0.621 0.365 0.365 0.363 900 2 2 1.25 5.06 1.35 4.95 3.15 3.15 2.55 1 Except for sample min/max, values reflect per trial averages; n = no. of field trials. 2 LAFT = lowest average field trial; HAFT = highest average field trial. 3 Residues were determined by a common moiety method that converts residues of NAA acetamide and NAA ethyl ester to NAA. Per trial averages were calculated by the study reviewer.NAA Summary of Analytical Chemistry and Residue Data DP#: D399621



### Page 14 of 16 Conclusions The submitted rambutan field trial data are adequate. Following one foliar directed application of the 3.5% SC formulation of NAA sodium salt at 90 and 900 ppm, re spectively , residues (and per trial averages) of NAA in/on rambutan fruit harvested at a 2 - day PHIwere 0.0786 - 0.636 (0.108 - 0.621) and 1.25 - 5.06 (1.35 - 4.95) ppm. Residue decline data were not submitted. An acceptable method was used for residue quantitat ion, and adequate data were submitted to support sample storage intervals and conditions. **Summary -**  **Pome Fruit Group (Crop Group 11 -**  **10)** Representative crops for the pome fruit crop group are apples and pears. D306440, 04/30/2009, G. Otakie 

### Per the re ferenced review this tolerance was revised to 0.15 ppm in 2009: “New HED tolerance assessment procedures incorporating statistical procedures (i.e. NAFTA MRLCalculator) subsequent to the NAA Registration Standard indicate the 0.1 ppm tolerance for NAA in/on Pome Fruits should be raised to 0.15 ppm.” **860.1520 Processed Food and Feed** There are no processed commodities associated with the proposed uses in the current petition **860.1650 Submittal of Analytical Reference Standards** Analy tical reference stan dards for 

## NAA are available at 

## the EPA National Pesticide Standards Repository . The tolerance expression includes only NAA, so this is sufficient. **860.1850/ 860.1900 Confined/Field Accumulation in Rotational Crops** There are no rotational crop data requi rements associated with the proposed uses in the current petition. **860.1550 Proposed Tolerances** Tolerances are established under 40CFR§180.155(a) for the combined residues of 1 - naphthaleneacetic acid and its conjugates calculated as 1 - naphthaleneacetic acid from the application of 1 - naphthaleneacetic acid, its ammonium, sodium, or potassium salts, ethy l ester, and acetamide in/on sweet cherry , fruit pome group 11, olive, orange, pineapple, and tangerine.NAA Summary of Analytical Chemistry and Residue Data DP#: D399621



### Page 15 of 16 A time - limited Section 18 emergency exception tol erance under 40CFR§180.155(b) is also established for avocado (expires 12/31/12). The established tolerances range from 0.05 ppm to 0.15 ppm. No Codex, Canadian, or Mexican maximum residue limits (MRL s) have been established for residues of (NAA), its salts, ester, and acetamide for the use in this petition. . **Table 10 Tolerance Sum**  **ma ry for NAA**  Commodity Established/Proposed Tolerance (ppm) Recommended

Tolerance (ppm) Comments; Correct Commodity

Definition 

### Tolerances Proposed Under PP#2E7991 Avocad o 0.05 Mango 0.05 Mamey Sapote 0.05 Rambuttan 3.0 2.0 Fruit, pome, group 11 - 10 0.15



### Tolerances That Need Amended Under PP#2E7991 Rambuttan Proposed 3.0 ppm (Section F) 2.0 --- 

### Attachments: Appendix I

– Tolerance Assessm ent Calculations **F. DOCUMENT TRACKING**  RDI: G. Otakie 10/03/12; S. Hummel 10/03/12 Petition Number: 2E7991 DP#: 399621 PC Code: 129032 Template Version September 2005NAA Summary of Analytical Chemistry and Residue Data DP#: D399621



### Page 16 of 16 Appendix I

– Tolerance Assessment Calculations

**NAA Rambutan**  **US 90 ppm 2**  **- da**  **y PHI Total number of data (n)**  4 **Percentage of censored data** 0% **Number of non -**  **censored data** 4 **Lowest residue** 0.079 **Highest residue** 0.636 **Median residue** 0.371 **Mean** 0.364 **Standard deviation (SD)** 0.297 **Correction factor for censoring (CF)** 1.000 **Proposed MRL estimate**

**- Highest residue**  0.636

**- Mean + 4 SD**  1.553

**- CF x 3 Mean**  1.092 **Unrounded MRL** 1.553 **Rounded MRL 2**  High uncertainty of MRL estimate. [Small dataset] **Residues (mg/kg) n**  0.0786 1 0.137 1 0.605 1 0.636 1