### 2 

# 1. Executive summary

The Environmental Fate and Effects Division (EFED) has completed the preliminary problem formulation for the ecological risk, environmental fate, endangered species, and drinking water assessments to be conducted as part of the registration review of 1

- n apthaleneacetic acid (NAA)

, and its sodium, potassium and ammonium salts, ethyl ester and acetamide ( T able 1 ) . The problem formulation describes the methods to be used during the completion of drinking water and ecological r isk assessments in support of registration review and provide s an ove rview of the environmental fate, ecological effects , and potenti al risks associated with the use of N AA as well

as uncertain ties unique to risk assessment of N AA , and its salts, ester and acetamide . This document also identifies additional studies that would be beneficial to the conduct of an ecological risk assessmen t. Major findings include the following.

Stressors of Concern

Inspection of the product labels shows that the products containing 1

- n apthaleneacetic acid (NAA) , and its sodium, potassium and ammonium salts, and acetamide may be applied foliarly. However, the ethyl ester of naphthalene acetic acid is only applied by brush, sponge or paint roller, or small hand held sprayer (to individual trees), “ applied to pruning cuts on the scaffold limbs, base of trunks and on rootstock suckers to control re

- sp routing.” Given the limited exposure expected for the ethyl ester compared to other chemical s in the family , the focus of the forthcoming ecological risk assessment will be on the acid (which is also used as a surrogate for the salts), and the acetamide f orms

. Environmental Fate Data Gaps

P h ysical and Chemical Properties: The registrant is requested to provide this important data for the acid (NAA) , its salts, ethyl ester and naphthalene acetamide , particularly the dissociation constants. In this respec t accuracy of the physical and chemical data contained in this document, which were obtained from sources other than submitted/accepted studies needs to be verified, for the salts, ethyl ester and acetamide.

Aerobic Soil Metabolism (835. 4 100 with 1

- naptha lene acetic acid (NAA) and naphthalene acet amide ): No aerobic soil metabolism study is available for NAA or any of its derivatives. At the present time, EFED is requesting a study to be conducted in four soils: two on the acid, and
two on the acetamide derivative

. No data has been identified on the dissociation of the acid derivatives and the requested studies are based on the assumption that the sodium, potassium

, and ammonium salts of this chemical are highly soluble and dissociate comp letely to the acid. If this is not the case

, then a n additional study is requested for one of the salts. In the absence of data, the Agency will assume that NAA and the amide are stable to aerobic soil metabolism.

Aerobic Aquatic Metabolism (835.4300 wi th 1

- napthalene acetic acid (NAA) and naphthalene acet amide ): No aerobic aquatic metabolism study is available for NAA or any of its derivative compounds. At the present time, EFED is requesting that studies to be conducted with naphthalene acetic acid an d it’s acetamide derivative in two sediment systems

. No data have been identified on the dissociation of the acid derivatives and the requested studies are based on the assumption that the sodium, potassium

, and ammonium salts of this chemical are highly

### 3

soluble and dissociate completely to the acid. If this is not the case

, then an additional study is

r equested for one of the salts. In the absence of data, the Agency will assume that the chemical s

are stable to aerobic aquatic metabolism.

The Agency is aware that a study is available for the acid in two sediment systems, submitted to the E uropean Commission . According to the E uropean Commission (EC) Draft Assessment Report 1 

### dated August 2008 , the DT 50 

### ’s 2 

### for the total system in two sediments are 6.2 and 9.5 days. Should it comply with Agency guidance, this study sh ould be submitted to the Agency . I f found acceptable or supplemental , the study may be used in the forthcoming Preliminary Ecological Risk As sessment.

Adsorption/Desorption (Batch Equilibrium) (835.1230 with 1

- napthalene acetic acid (NAA) and naphthalene acet amide ): No mobility studies are available for NAA or any of its derivative compounds. At the present time, EFED is requesting a study to be conducted with NAA (the acid) in t wo soils and a sediment

, plus a study for napthalene acetamide in two soils and a sediment

. The soil used should be the most representative of typical agricultural use areas

. No data ha ve been identified on the dissociation of the acid derivatives and the requested studies are based on the assumption that the sodium, potassium and ammonium salts of this chemical are highly soluble and dissociate completely to the acid. If this is not the case , then a n additional study is requested for one of the salts

. In the absence of data, conservative assumptions will be made for NAA and its derivative compounds

. The Agency is aware that a batch equilibrium study

, conducted in three soils, is availab le for the acid

. This study was submitted to the E C and is cited in the E C Draft Assessment Report

. According to the E C report , naphthalene acetic acid’s K d 

### values range from 0.40 to 2.72 cm 3 

### /g (or mL/g), K OC 

### values range from 68.5 to 138 cm 3 

### /g OC 

### , K F 

### va lues range from 0.297 to 1.77 cm 3 

### /g, and K FO C 

### values range from 50.3 to 88.5 cm 3 

### /g OC



### . Should it comply with Agency guidance, this study sh ould be submitted to the Agency. If the study is found to be acceptable or supplemental, it may be used in the Preliminary Risk Assessment.

Envi ronmental Chemistry Method and A ssociated Independent Laboratory Validation (Water) (850.6100 with 1

- napthalene acetic acid (NAA) and naphthalene acetamide ) : An environmental chemistry method (ECM) and its associated inde pendent laboratory validation (ILV), for the analysis of naphthalene acetic acid, naphthalene acetamide and their possible environmental degradates of ecological and/or human health concern in water are required . A method for the analysis of NAA in sedime nt has not been deemed ne cessary since NAA appears to exist as an anion in the environment and is not expected to be associated with sediments.

Ecological Effects Data Gaps

Honey B ee Adult Acute Contact T oxicity ( 

### 850.3020 with TGAI 1

- naphthaleneacetic acid) : C 

### urrently the Agency has no honeybee acute contact toxicity data with any of the NAA actives.

1 European Commission Draft Assessment Report (DAR) (public version). Initial risk assessment provided by the rapporteur Member State France for the existing active substance 1

- Naphtylacetic Acid (1

- Naphthalene Acetic Acid). Volume 3, Annex 3, part 5, B.8. Environmental fate and behaviour. August 2008.

2 Dissipation time for 50% of the initial residue (days).

### 4

The Agency is aware of honeybee acute contact toxicity data submitted to the European Union. Should it comply with Agency guidance, this study should be s ubmitted to the Agency. If it is found to be acceptable or supplemental, it may be used in the Preliminary Risk Assessment.

Honey B ee Adult Acute Oral T oxicity ( Non

- Guideline Special Study , OECD 213 with 

### TGAI 1

- naphthaleneacetic acid) : NAA an d it s related actives are systemic ally transported in plants. Therefore, bees may be exposed to NAA residues through ingestion of contaminated pollen and
nectar. This study is needed to evaluate potential risks to adult honey bees resulting from acute oral expo sure to NAA. The Agency is aware of honeybee acute oral toxicity data submitted to the European Union. Should it comply with Agency guidance, this study should be submitted to the Agency. If it is found to be acceptable or supplemental, it may be used in the Preliminary Risk Assessment.

Honey B ee 10 day Adult C hronic T oxicity (Non

- Guideline, Special Study with 

### TGAI 1

- naphthaleneacetic acid ) : NAA and its related actives are systemically transported in plants. Therefore, bees may be exposed to NAA resid ues through ingestion of contaminated pollen and
nectar. This study is needed to evaluate potential risks to adult honey bees resulting from chronic oral exposure to NAA.

Honey Bee Larval Acute Toxicity ( Non

- Guideline Special Study , OECD 234, with 

### TGAI 1

- naphthaleneacetic acid ) : NAA and its related actives are systemically transported in plants. Therefore, bees may be exposed to NAA residues through ingestion of contaminated pollen and nectar. This study is needed to evaluate potential risks to larval honey bees resulting from acute exposure to NAA via contaminated pollen and nectar which is brought back to the hive, processed and fed to larvae.

Honey Bee Larval Chronic Toxicity (Non

- Guideline Special Study with 

### TGAI 1

- naphthaleneacetic acid): NAA a nd its related actives are systemically transported in plants. Therefore, bees may be exposed to NAA residues through ingestion of contaminated pollen and nectar. This study is needed to evaluate potential risks to developing larval honey bees resulting from chronic (repeated dose) exposure to NAA via contaminated pollen and nectar which is brought back to the hive, processed and fed to larvae.

Avian Reproduction (850. 2300 ) with TGAI naphthalene acet amide. No data have been submitted on the chronic tox icity of NAA or its derivatives to birds. Chronic avian reproduction data for a similarly structured compound with the same mode of action (quinclorac; NOAEC = 500

- 1000 ppm ; MRID 44084501 & 44129201 ) in addition to that for other synthetic auxins (amino pyralid, dicamba; NOAEC = 800

- 2600 ppm) suggest low chronic toxicity to birds. Given that a predicted EEC of 50 ppm is expected on avian dietary items (short grass), additional chronic toxicity data for NAA and its derivatives is considered of low value. In absence of data, EFED will bridge chronic toxicity for birds using data from similar compounds.

Aquatic Plant Toxicity testing with Freshwater Diatom, Freshwater Blue

- green algae, and Marine diatom (850.4 5 00 with 

### TGAI 1

- naphthaleneacetic acid and Naphthaleneacetamide ) : The Agency currently has limited data with which to assess the risk to non

- target aquatic plants. Only a single species has been tested with a 24.2% a

. i

. end use product (K

- Salt Fruit Fix 800). To adequately assess potential effects of these plant growth regulators additional data will be need ed

### 5

using the NAA and the amide form of NAA . T he Agency is aware of algal toxicity data for 2 species submitted to the European Union using technical grade test material and these studies should be submitted to the Agency. If found to b e acceptable or supplemental, they may be used in the Preliminary Risk Assessment.

Acute Toxicity to Freshwater and Saltwater Fish (850.1075) with the TGAI N aphthalene a ceta mide . For freshwater and saltwater fish, toxicity data are needed for assessing risk from the amide form of NAA, since no data have been submitted

. In absence of such data, EFED is proposing to bridge results from similarly structured compounds of the same mode of action ( e.g., Quinclorac and Quinmerac).

Acute Toxicity to Freshwater and Saltwater Invertebrates ( 850.1010, 850.10 35 ) with the TGAI N aphthaleneaceta mide

. For freshwater and saltwater invertebrates, toxicity data are needed for assessing risk from the amide form of N AA, since no data have been submitted. In absence of such data, EFED is proposing to bridge results from similarly structured compounds of the same mode of action ( e.g., Quinclorac and Quinmerac).

Chronic Toxicity to Freshwater Fish (850.1400 ) with the T GAI Naphthalene A ceta mide

. For chronic toxicity to freshwater fish, toxicity data are being requested for the amide form of NAA, since no data have been submitted and the margin of safety between exposure and toxicity is sufficiently small (10X) based on QSAR model predictions. In absence of such data, EFED is proposing to bridge results from similarly structured compounds of the same mode of action ( e.g., Quinclorac and Quinmerac).

Chronic Toxicity to Freshwater Invertebrates (850.1300 ) with the TGAI N a phthalene a ceta mide . For chronic toxicity to freshwater invertebrates, toxicity data are being requested for the amide form of NAA, since no data have been submitted

. In absence of such data, EFED is proposing to bridge results from similarly structured co mpounds of the same mode of action ( e.g., Quinclorac and Quinmerac).

Seedling Emergence and Vegetative Vigor (850.4100; 850.4150) with Naphthaleneacetamide

. Terrestrial plant toxicity testing has been submitted for the potassium and sodium salts of NAA. No terrestrial plant data have been submitted for products containing the amide or ester forms of NAA. Exposure of terrestrial plants to the NAA ester is expected to be negligible due to its limited use pattern. Unlike the ester form of NAA, exposure is expected for the amide form of NAA. Therefore, submission of toxicity data that can be used to assess the effect of naphthaleneacetamide on terrestrial plants is recommended

.

Uncertainties

Very little environmental fate data is available for these compounds. With previous ecological risk assessments, q uantitative structure activity relationships (QSAR) and limited available data were used to derive some of the input parameters for the aquatic models. Major uncertainties with r espect to these chemicals are related to the absence of measured values for fate parameters.

### 6

Furthermore, there is lack of information about the degradates of NAA and derivatives . Possible degradates were previously identified using the CATABOL 3 

### program as described below.

Regarding the application rates on the numerous crops that are currently approved for use, if there are any uncertainties, as in the case of rambutan and potato seed pieces in Table s 2 a to 2d (as shown in footnotes to the table s ), the Agency may make conservative assumptions regarding the application rates. The registrant is required to review these tables and provide updated information as needed.

The ecological effects dataset for NAA and it s related salts

, ester , and amide is not consistent across any one active. This requires that the Agency make assumptions for one active based on the known toxicological characteristics of the tested actives. Alt hough the ester form appears to be more toxic than NAA and the related salts to aquatic animals , the Agency is not asking for further data on the ester because its current use patterns limit expected off target exposure

. Since the salts dissociate to the NAA in the environment, the data requests are for this active ingredient

. T he Agency is aware of additional data submitted to support European registrations and several appear to coincide with current inadequacies noted in the dataset which has been submitted to support U.S. registration for these actives. These studies conducte d with the NAA may help to alleviate uncertainties that will arise during the Registration Review process and could satisfy unfulfilled guideline needs for U.S. assessment purpos es regarding risk to honeybees, chronic toxicity to aquatic organisms

, and acu te toxicity to aquatic plants.



# 2. Introduction

1

- Naphthaleneacetic acid (NAA) is a systemic plant growth regulator that mimics auxin ( e.g. , indole

- 3

- acetic acid) a naturally occurring plant growth hormone that is important in seed and

r oot development. In this respect, NAA and related compounds are similar to 2,4

- D, another auxin mimic, but distinct from 2,4,5

- T, an anti

- auxin ( Cooke et al. 200 2 ). NAA and related compounds are formulated as six different active ingredients listed in Ta ble 1

. Table 1. Chemical structures of Naphthalene acetic acid and related active ingredients 1



### Name and CAS Number Structure 1

- Naphthalene acetic acid (NAA) CAS No. 86

- 87

- 3 PC Code 056002 SMILES Code: O=C(O)Cc(c(c(ccc1)cc2)c1)c2 Molecular Weight: 186.2 g/mol VP: 3 x 10

- 1 torr Solubility: 420 mg/L at 20 o C

3 CATABOL is a model that predicts degradation pathways of a chemical in the presence of mixed population of environmental microorganisms (source: O ECD Series on Testing and Assessment Guidance Document on the Validation of (Quantitative) Structure

- Activity Relationship [(Q)SAR] Models. OECD Publishing. 2007. 154 pp. Case Study 4: CATABOL for biodegradation).

### 7 Name and CAS Number Structure

Sodium 1

- naphthalene acetate CAS No. 61

- 31

- 4 PC Code 056007 Molecular Weight: 208.2 g/mol VP: 3.1 x 10

- 6 torr Solubility: Refer to Table 5



### Potassium 1

- naphthalene acetate CAS No. 15165

- 79

- 4 PC Code 056003 Molecular Weight: 224.3 g/mol VP: 3.1 x 10

- 6 torr Soluble in Water



### Ammonium 1

- naphthalene acetate CAS No. 25545

- 89

- 5 PC Code 056004 Molecular Weight: 203.2 g/mol VP: 3.1 x 10

- 6 torr Solubility: 420 mg/L at 20 o C



### 1

- naphthalene acetic acid ethyl ester Ethyl 1

- naphthaleneacetate CAS No. 2122

- 70

- 5 PC Code 056008 Molecular Weight: 214.3 g/mol VP: 1.5 x 10

- 4 torr Solubility: Refer to Table 5



### 1

- naphthalene acetamide CAS No. 86

- 86

- 2 PC Code 056001 Molecular Weight: 185.2 g/mol VP: 2.8 x 10

- 7 torr Solubility*: 170 mg/L at 20 o C SMILES Code: c12c(cccc1CC(N)=O)cccc2

1 Structures were obtained from Alan Wood’s website at http://www.alanwood.net/pesticides/a

na phthaleneacetic%20acids.html

. Molecular Weight and vapor pressure from URL: http://www.chemnet.com/cas/supplier.cgi?terms=2122

- 70

- 5&l=en&exact=dict&f=plist&mark=&submit.x=29&submit.y=16 So l ubility from: For acid: http://sitem.herts.ac.uk/aeru/iupac/ For Na

- Salt http://www.guidechem.com/cas

- 86/86

- 87

- 3.html and for others: http://www.sumitomo

- chem.com.au/sites/default/files /pdf/msds/grochem

- naa20_msds.pdf



### . In order to determine if additional data were needed for conducting ecological risk assessment as part of Registration Review, EFED evaluated the most recent ecological risk assessments for NAA and related compounds in as sociation with the update d toxicity, exposure, and usage information

. In 2004, EFED conducted an ecological risk assessment in support of a Revised Registration Eligibility Document for all use s of n apthaleneacetic acid and related comp ounds

### 8

(D306433 dated 10/26/04)

. In 2011

, a FIFRA Section 18 e mergency exemption was granted for the p rod uct Rejuvenate Seed Treatment, c ontaining p otassium n aphthaleneacet ate , on p otato

s eeds, and the p roduct Mitigate PGR 4



### , c ontaining sodium n aphthaleneacet ate , on p otato f ol iage in Idaho ( D 376108 ) . A FIFRA Section 3 n ew u se assessment was also conducted in 2011 for the use of potassium naphthaleneacetate and sodium n aphthalene a cetate on potato s eeds and/ or on
p otato foliage for the new products RenewTM PGR and RenewTM Concentrate PGR ( D 388693 + )

. The latest risk assessment was issued in 2012 ( D402377 ), for 1

- naphthaleneacetic acid (NAA)

, sodium naphthaleneacetate

, and ethyl naphthaleneacetate uses on certain tropical f ruits (mango, avocado, mamey sapote, and rambutan), various additional pome fruits ( azarole, crabapple, loquat, mayhaw, medlar, Asian pear, quince, Chinese quince, Japanese quince, tejocote for the products Tre

- Hold ® 

### Sprout Inhibitor A

- 112, and Fruitone ® 

### L . Previously the only pome fruits approved were apples and pears. The proposed new uses on r ambutan, avocado, mamey sapote

, and m ango were at a maximum seasonal rate of 0.22 lb a.e

. /A and 0.11 lb a.e. /A for rambutan. 5



### For more information on use and usage, please see the LUIS Report ( USEPA 2014a ) and BEAD Chemical Profile document ( USEPA 2014b), both of which are located in the docket.

In addition, EFED considered the latest Agency science policies and risk assessment methodologies. The structure of NAA , as well as the chemical names and other identifiers can be found in Table 1 and Appendix A

.



# 3. Use Characterization

According to the Screening

- Level Usage Analysis (SLUA) (USEPA 2014a) , NAA and derivative compounds are primarily used on apples (average 5000 lb A.I.), followed by pears (2000 lb A.I.). Two other crops are cited in the report (avocadoes and olives, with <500 lb A.I. each). The SLUA reporting period is 2004

- 2012. Sources of the SLUA include USDA

- NASS (United States Department of Agriculture's National Agricultural Statistics Service), Private Pesticide Market Research, and California Department of Pesticide Regulation (CDPR)

. The SLUA included all PC Codes for NAA, its salts, ethyl ester an d acetamide.

The latest crop use map for NAA w as prepared from 2011 agricultural statistics ( Figure 1 )

. Updated maps are proposed when the 2012 Agricultural Census Report results are published by USDA. According to the map, it appears that NAA is mainly applied in the Pacific Northwest, California, the northeast, the midwest

, and part of the regions surrounding Virginia, Maryland and West Virginia. It appears that its use has declined over the past seven years, with a slight increase in 2011. T he map i n Figure 1 included only the napthalene acetic acid

. The map for n apthalene acetamide (which is not included below) shows that it is used more prominently in the Pacific N orthwest areas of U.S. and California.

4 PGR=Plant Growth Regulator.

5 The abbrev iation a.e. refers to acid equivalents ( i.e. , lbs of NAA, its salts and ester, expressed as lbs of NAA).

### 9

Figure 1 . USGS Naphthalene Acetic Acid Agricultural Use, 2011 (source: http://water.usgs.gov/nawqa/pnsp/usage/maps/compound_listing.php?year=2011&hilo=L )

Recent product registration information ( excluding technical grade products for formulation) obtained from the Office of Pesticide Programs Information Network (OPPIN) lists 2 products for 1

- naphthaleneacetamide, 12 products for 1

- naphthaleneacetic acid (NAA) , 11 products for
p otassium 1

- naphthal eneacetate, 5 products for a mmonium 1

- naphthaleneacetate, 5 products for

s odium 1

- naphthaleneacetate and 5 products for e thyl 1

- naphthaleneacetate.

1

- naphthaleneacetamide is approved for use on ornamentals, apples, pears and is applied as a root treatment

. It is also used for thinning apples and pears.

1

- naphthaleneacetic acid (NAA) is approved for use on avocados, ornamental plants, trees and shrubs, herbs, vegetable crops, apples, citrus transplants, gooseberry, grape (transplants and non

-

### 10

bearing), nut trees (non

- bearing), pome fruit (non

- bearing), and stone fruit (non

- bearing). It is

a pplied to roots only.

Potassium 1

- naphthaleneacetate is approved for use on apples, citrus (includes oranges, tangelos, mandarins), olives, pears and as a potato seed treatment. Ground

, broadcast

, and aerial application are permitted on current labels

.

Ammonium 1

- naphthaleneacetate is approved for use on apples, olives, citrus (includes oranges, tangelos, mandarins), pears, sweet cherries, and ornamental f ruit trees. Ground

, broadcast

, and aerial application are permitted on current labels

.

Sodium 1

- naphthaleneacetate is approved for use on apples, crabapples, pears, and quince, and has a pending application for use on potatoes. Ground

, broadcast

, and ae rial application s are permitted on current labels

. Ethyl 1

- naphthaleneacetate is registered for use on apples, ornamental trees, shrubs, numerous tree species (as bark, prune wound, or foliar treatment), avocados (dormant application), black willow, C hris tmas trees, citrus, coastal redwood, crabapple, quinces, loquat, mangos, nectarines, olives, pears, pomegranate and further pending uses on avocados (non

- specified). Currently it is labeled for application to roots or basal bark only.

Table 2 a . Uses Sit e and Application Information for 1

- Napthalene Acetic Acid (NAA) , based on the 2007 revision of the RED, and labels

USE MAX SINGLE APP. RATE (lb A.E./A) 1 MAX N O.

OF APPS. AT MAX RATE SEASONAL

APP. RATE (lb A.E ./A) 1 MINIMUM

INTERVAL BETWEEN APP S . (days) APP.

METHOD 1 INCORP.

DEPTH (inches) Potted Plants, Trees, Shrubs, Flowers or House Plants 0.11 1 0.11 5 S 0

Apples, pears 0.11 3 0.33 5 F 0 Bedding plants, vegetables and nursery stock (including woody ornamentals, deciduous hardwoods,
evergreens, ground covers, and perennials ) N D NS N D 7

- 14 days
or every watering F, SR, W 0

Nursery stock cuttings including Woody ornamentals, Deciduous hardwoods, Evergreens, Ground Covers, and Perennials ND 1 ND N/A D 0

Shrubs, Flowers, Groundcovers, Houseplants, and the Following Non

- Bearing Plants: Citrus Fruits, Pome Fruits, Stone Fruits, Berries, Tree Nuts, Date Palm, and Grapes, Rose, Arborvitae, Gardenias, flowering trees and other ornamentals in bare root transplant or from containers ND NS ND 7 SD 0

Annual and perennial flowers (bedding plants), Groundcovers such as, Ivy, Iceplants, Geranium, Cotoneaster, Barberry, & Ajuga ND NS ND 7 SD 0

### 11 USE MAX SINGLE APP. RATE (lb A.E./A) 1 MAX N O.

OF APPS. AT MAX RATE SEASONAL

APP. RATE (lb A.E ./A) 1 MINIMUM

INTERVAL BETWEEN APP S . (days) APP.

METHOD 1 INCORP.

DEPTH (inches) Non

- Bearing Plants such as Citrus Fruits, Pome Fruits, Stone Fruits, Berries, Tree Nuts, Date Palm, and Grapes ND 3 ND NS SD 0

Turf and Sod Farms ND NS ND NS SD 0 1 A.E. = acid equivalents; S = “ Thoroughly saturate the soil, around the plant with the solution”; SR = soak roots for 15 minutes before transplanting; W = water plants; F = foliar; D = Dip the basal end of cutting, individually or in bunches, into the solution for 3

- 5 seconds; SD = soil drench ( apply solution to root area in transplanting hole and then cover roots with soil or apply to thoroughly saturate roots at time of planting )

. 2 Wh ere the application rate is not determined, it appears to be 0.11 lb a.e./A, similar to other crops. EPA seeks clarification on the application rate, the number of applications per season and per year, and the time interval between applications.



### Table 2b . Uses Site and Application Information for 1

- Napthalene Acetic Acid Salts (Sodium, Potassium and Ammonium), based on the 2007 revision of the RE D, and labels

USE MAX SINGLE APP. RATE (lb A.E./A) 1 MAX NO.

OF APPS. AT MAX RATE SEASONAL

APP. RATE (lb A.E ./A) 1 MINIMUM

INTERVAL BETWEEN APP S . (days) APP.

METHOD 1 INCORP.

DEPTH (inches) Rambutan 0.11 1 0.11 2 5 TP 0 Citrus (mandarin, oranges, tangelo s, tangerines, and non

- bearing) 0.11 3 0.33 5 G, A, SD 0

Cherries, some non

- bearing fruit and
nut trees 0.11 3 0.33 5 G, A, SD 0

Ornamental plants (herbaceous, non

flowering trees, woody shrubs and vines), shade trees, and residential fruit, and ornamental trees 0.11 3 0.33 5 G, A, SD 0

Holly (shelterbelt) 0.11 3 0.33 5 Dip holly boughs in solution after cutting 0

Apples, pears 0.11 3 0.33 5 G, A, SD 0 CG 11

- 10 Pome fruits: A zarole, crabapple, loquat, mayhaw, medlar, Asian pear, quince, Chinese quince, Japanese quince, tejocote and cultivars, varieties and/or hybrids of these 0.11 3 0.33 5 G, A, SD 0

Olives 0.33 1 0.33 N/A AB 0 Potato seed pieces 0.0004 3 1 0.0004 N/A ST 3 4
1 A

. E . = acid equivalents; N/A = not applicable; G = ground; A = aerial; SD = dip or soil drench; ST = seed treatment; AB = airblast; B = brush, sponge or paint roller (to individual trees); T P = t reat rambutan panicles spraying a solution to runoff. 2 Even though the label is not clear on the application rate

, it appears to be 0.11 lb a.e./A, similar to other crops. 3 The equivalent application rate for seed piece treatmen t is an estimate. EPA seeks clarification of the maximum application rate for seed piece treatments. 4 Shallowest depth of planting potatoes was obtained from the following source : http://www.cals.uidaho.edu/potatoes/Research&Extension/Topic/Seed&Planting/EffectsOfRemovingSeedPieces&PlantingDepthO nPotatoYield

- 99.pdf (William H. Bohl and Stephen L. Love. 1999. Effects of Removing Seed Pieces and Planting Depth on Potato Yield ; accessed June 16, 2014 ). Furthermore , the following article site explores depths of incorporation starting from 2

- 9 inches: http://link.springer.com/article/10.1007/BF02861893 ( Lorenz, O.A. Effect of planting depth on yield and tuber set of potatoes. American Potato Journal. November 1945, Volume 22, Issue 11, pp 343

- 349 ; access ed June 16, 2014 ).

### 12

Table 2 c . Uses Site and Application Information for Napthalene Acetamide, b ased on the 2007 R evision of the RE D , and labels

USE MAX SINGLE APP. RATE (lb A.E./A) 1 MAX NO.

OF APPS. AT MAX RATE SEASONAL

APP. RATE (lb A.E ./A) 1 MINIMUM

INTERVAL BETWEEN APP S . (days) APP.

METHOD 1 INCORP.

DEPTH (inches) O rnamental plants (herbaceous

, woody shrubs and vines), shade trees, and ornamental trees 0.11 2 3 0.33 5 1 Treat root cuttings 0

Apples, pears 0.11 3 0.33 5 G, A, F 0 1 A

. E . = acid equivalents; F = foliar

. 2 The application rate on ornamental plant cuttings for planting appears to be much lower than stated in the table. The info rmation provided in the table was derived from the RED amendment document.



### Table 2 d . Uses Site and Application Information for Ethyl 1

- Napthalenea cetate, based on the 2007 R evision of the RE D, and labels

USE MAX SINGLE APP. RATE (lb A.E./A) 1 MAX NO.

OF APPS. AT MAX RATE SEASONAL

APP. RATE (lb A.E ./A) 1 MINIMUM

INTERVAL BETWEEN APP S

. (days) APP.

METHOD 1 INCORP.

DEPTH (inches) Apples 0.11 3 0.33 5 B 0 Olives 0.33 1 0.33 N/A B 0 Or namental Citrus, P omegranate and N ectarine (nectarine is disallowed in CA) 0.11 3 0.33 5 B 0

O rnamental plants (woody shrubs and vines), and/or shade trees 0.11 3 0.33 5 B 0

Avocado, mamey sapote, mango 0.11 2 0.22 45 B 0 Azarole, Crabapple, Loquat, Mayhaw, Medlar, Asian Pear, Quince, Chinese Quince, Japanese Quince, Tejocote a nd Cultivars, Varieties and/or h ybrids of t hese
t rees 0.11 3 0.33 5 B 0

1 A.E. = acid equivalents; B = brush, sponge or paint roller, or small hand held sprayer (to individual trees)

, “ applied to pruning cuts on the scaffold limbs, base of trunks and on rootstock suckers to control resprouting.”


### In cases where application rates and other use parameters are not clearly stated on product labels, EPA may make conservative assumptions.

Acc ording to the 2007 Reregistration Eligibility Decision document , the following label restrictions were imposed to the naphthalene acetic aci d and derivative s relative to Environmental Hazards and spray drift management :

Environmental Hazards

“Do not apply directly to water. Do not contaminate water when disposing of equipment washwaters or rinsate.”

Spray Drift Management

"A variety of factors including weather conditions ( e.g. , wind direction, wind speed, temperature, relative humidity) and method of application ( e.g. , ground, aerial, airblast)

### 13 can influence pesticide drift. The applicator and grower must evaluate all factors and

make appropriate adjustments when applying this product."

Wind S peed R estriction :
"Do not apply when wind speeds are greater than 10 mph at the application site."

Specific language for orchard air blast :
“Sprays must be directed into the crop canopy.”

“Outward pointing nozzles should be turned off at row ends and when spraying outer rows.”

"For ground based applications and aerial applications, use only medium or courser spray droplets (or nozzles) according to ASABE (S572) definition for standard nozz les.”



# 4. Conclusions from Previous Risk Assessments

a. Ecological Risk Assessment

In the 2004 ecological risk assessment to support the revised RED for NAA , EFED concluded that NAA and related compounds d id not present significant potential for risks to bird s, mammals, fish, aquatic invertebrates, or aquatic plants. However, an assessment based on conservative exposure assumptions indicate d that endangered terrestrial plants may be at risk. Risks to terrestrial insects c ould not be quantified due to lack of t oxicity data

, although the limited information available at that time for other insect species did not suggest a high potential for adverse effects.

The latest ecological risk assessment was completed in 2012 ( D402377 ), for the use of 1

- naphthaleneacetic acid (NAA)

, sodium 1

- naphthaleneacetate

, and ethyl 1

- naphthaleneacetate on certain tropical fruits and pome fruits

. EFED based its findings on a previous assessment of the use of the se three active ingredients on avocado (D361448, April 13, 2009)

. In tha t assessment, EFED concluded that the proposed use of two applications at 0.22 lb a.e./A at 45 day intervals should not pose acute or chronic risk to non

- target animals . The only level of concern (LOC) exceedance was for endangered species of semi

- aquatic (terrestrial) plants (RQ = 4.4 , compared to an LOC of 1).

Table 3 contains a summary of the ecological risk assessment conclusions made by t he Agency over the past 10 years with NAA and related compounds.

### 14

Table 3 . Summary of Risk Concerns Identified for Napthalene acetic acid (NAA) and related compounds in Previous Assessments

Birds Mammal Terr

.

Plants Terr

. Inverts Fish BCF Aquatic Inverts Aquatic

Plants Groundwater

Contamination Persist en t Degrades of Concern No No Yes N D No No No No No No N D Yes = at least one LOC has been exceeded in previous assessments; No = LOCs have not been exceeded in previous
assessments , however toxicity database was incomplete ; N D = RQs have not been calculated previously.



## b. Drinking Water Exposure Assessments

The latest drinking waters assessment was completed in 2012 ( DP Barcode D399622 ) for the uses of for 1

- naphthaleneacetic acid

, sodium 1

- naphthaleneacetate

, a nd ethyl 1

- naphthaleneacetate on certain tropical fruits and pome fruits

. Previously the only pom e fruits included o n the labels

were apples and pears. The proposed new uses on r ambutan, avocado, mamey sapote

, and m ango had a maximum seasonal rate of 0.22 lb a.e./A and 0.11 lb a.e./A for rambutan. Based on an inspection of the new uses of NAA and it s derivatives , it was found that olives still represent ed the scenario with the highest exposure and consequently the highest EDWCs (with an application rate of 0.33 lb a.e./A/ application in a single application per season; DP Barcode D 387171 ). Therefore, the drinking water assessment results d id not change from the previous ones. Table 4 displays a summary of the results.

Table 4 . Maximum Tier I Estimated Drinking Water Concentrations (EDWCs) for drinking water assessment based on airblast application of 1

- naphthalene acetic acid and its derivatives (collectively known as naphthalene acetates) on olives
DRINKING WATER SOURCE (MOD EL USED) USE (rate modeled per crop cycle) MAXIMUM ESTIMATED DRINKING WATER CONCENTRATION (EDWC) ( ppb) Groundwater (SCI

- GROW) Olives (0. 33 lb A.E ./A) Acute and Chronic 0.0226
Surface water (FIRST) Olives (0. 33 lb A.E ./A) Acute 22.3 Olives (0. 33 lb A.E ./A) Chronic 2.99 A.E. = acid equivalents



### A new drinking water assessment will be necessary following review of requested fate and transport data are available and used in models available at that time. In this respect, it is noted that current models are the surface water concentration calculator (SWCC) for drinking water from surf ace water and PRZM ground water (PRZM

- GW) for ground water; these models are different from those used in obtaining EDWCs in previous assessments. The SWCC is similar to the previous PRZM/EXAMS, but different than FIRST (a Tier 1 model) , which was used in previous assessments. PRZM

- GW is an additional groundwater model that can be used both in the Tier 1 mode and Tier 2 mode.



## c. Clean Water Act Programs

Napthalene acetic acid (NAA) is not identified as a cause of impairment for any water bodies listed as impaired under section 303(d) of the Clean Water Act at http://iaspub.epa.gov/tmdl_waters10/attains_nation_cy.cause_detail_303d?p_cause_group_id=88 5

. Furthermore, n o Total Maximum Daily Load (TMDL) criteria have been developed for

n apthalene acetic acid (NAA)

. Aquatic benchmarks have not been established for NAA and

### 15

derivatives at http://www.epa.gov/oppefed1/ecorisk_ders/aquatic_life_benchmark.htm . Any data submitted or otherwise located as part of the registration review process may be used to establish aquatic life benchmarks if applicable.



# 5. Environmental Fate and Transport

A summary physicochemical and environmental fate/transport properties of NAA and some of its derivatives , including measured and modeled parameters, values, data sources, and comments, is included in Table 5 . Several of the parameters were obtained from the Hazardous Substances Data Bank (HSDB), available at http://toxnet.nlm.nih.gov/cgi

- bin/sis/htmlgen?HSDB

, accessed 0 7/25 /14. According to the HSDB fact sheet ...“All data are referenced and derived from a core set of books, government documents, technical reports and selected primary journal literature. HSDB is peer

- reviewed by the Scientific Review Panel (SRP), a committee of experts in the major subject areas within the data bank's scope. ” (Refer to the following website for further information http://www.nlm.nih.gov/pubs/factsheets/hsdbfs.html

, accessed 0 7/25 /14 .) However, the data have not been reviewed by the EPA.

Table 5. Summary of physical/chemical and environmental fate and transport properties of NAA (data in bold) and some of its derivatives

PARAMETER VALUE(S) (units) SOURCE COMMENT
Chemical Name 1

- naphthalene acetic acid

– – Molecular Formula C 12 H 10 O 2

– –
Molecular Weight 186.21 2007 RED Also in HSDB

Water Solubility 420 mg/L for NAA (2 6 o C) 3400 mg/L for the sodium salt 105 mg/L for the ethyl ester (25oC) MRID 40522903

, MRID 40523003, MRID 47505905 Also EPISUITE v.4.1 and HSDB 1

Vapor Pressure (25 o C) 0.3 T orr for NAA MRID 40522903 C onsidered representative for NAA since it is a measured value. Even though the VP for NAA (the acid) is high, it is not expected to volatilize substantially under typical environmental conditions since it is expected to dissociate, and anions do not volatilize.

9.57 x 10

- 6 T orr for NAA EPISUITE v.4.1

–

Henry’s Law constant 1.75 x 10
- 4 atm

- m 3 /mol Calculated Calculated from vapor pressure (0.3 T orr) and water solubility (420 mg/L)

.

pKa ( 25oC ) 3.5 for the acid ( Dissociation constant = 3.16 x 10
- 4 ) MRID 40522903 Exists primarily in the dissocia ted form in the environment. This value is considered representative for the dissociation constant for

NAA

.

4.23 for the acid EPISUITE v.4.1 and HSDB 2

–

174 (Log K OW = 2.24) EPISUITE v.4.1 and HSDB 3

–

### 16 PARAMETER VALUE(S) (units) SOURCE COMMENT

Octanol

- Water Partition Coefficient (K OW , unspecified temperature ) 2.29x10 3 (Log K OW = 3.36) for the ethyl ester MRID 47505902

–

Hydrolysis Half

- life (pH 5, 7, 9) NAA: stable; there are no hydroly z able functional groups.

Acc. No. 00 129382 NAA is not expected to hydrolyze

under environmental conditions. Ethyl

- 1

- naphthaleneacetate : pH 5 = stable; pH 7 = 266 days; pH 9 = 7.4 days, the degradate is the 1

- naphthaleneacetate anion. 1

- Naphthaleneacetamide was stable at the three pHs tested.

Aqueous Photolysis Half

- life (days) 4 Crosby and Tang (1969) 4 HSDB 5 Photolysis may be an important

process following exposure of an aqueous solution of NAA to 4 days of sun light NAA degraded completely to o

- phthalic acid and minor amounts of 1

- naphthoic acid, 1

- methylnaphthalene, 1

- naphthalenemethanol, and 1

- naphthaldehyde

Soil Photolysis Half

- life A half

- life was not reported in this study. HSDB 6 Exposure of NAA to UV light and sunlight produced 1

- hydroxymethyl naphthalene, 1

- naphthaldehyde, naphthalene

- 1

- carboxylic acid and 1

- methyl naphthalene under aerobic conditions. Anaerobically, only the 1

- methyl naphthalene was observed. Phthalic acid has also been observed. T h is study was not available for review

. Photolysis in Air t 1/2 = 0.289 days EPISUITE v.4.1 Hydroxyl radical reactions

Aerobic Soil Metabolism Half

- life t 1/2 = 10 days HSDB 7 H a lf

- life attributed to microbial degradation. T he cited study was
not available for review

.

Organic Carbon Partition Coefficient (K OC ) 24.82 mL/g OC EPI SUITE v.4.1 A nions generally do not adsorb more strongly to organic carbon and clay than their neutral counterparts

. K OC may be sensitive to pH. Terrestrial Field Dissipation Not available Not available

–

Bioconcentration Factor ( Cyprinus carpio ) BCFs of 0.15

- 0.59 and <1.7

- 4.2 were measured in carp for NAA at test chemical conc entrations of 0.5 and 0.05 mg/l, respectively

. HSDB 8 The cited study was not available for review by the EPA. Cited references: 1 Yalkowsky SH, He Y, eds; Handbook of aqueous solubility data. Boca Raton, FL: CRC Press p. 833 (2003) 2 Kortum G et al; Dissociation Constants of Organic Acids in Aqueous Solution. International Union of Pure and Applied Chemistry. London: Butterworth (1961) 3 Sangster J; LOGKOW Databank. Sangster Res. Lab., Montreal Quebec, Canada (1994) 4 Crosby, D.G., Tang, C.S. 1969. Photodecomposition of 1

- Naphthaleneacetic Acid. J. Agr. Food Chem. 17(6), 12 91

- 1293

### 17

5 Crosby DG; Adv Chem Ser 111: 173

- 88 (1972); and Crosby DG; pp. 568

- 76 in Advances in Pest Sci III. Geissbuhler H, ed. Oxford: Permagon Press pp. 568

- 76 (1979) 6 Menzie, C.M. Metabolism of Pesticides. U.S. Department of the Interior, Bureau of Sport Fisheries and Wildlife, Publication 127. Washington, DC: U.S. Government Printing Office, 1969., p. 25 7 Weber JB; pp. 15

- 41 in Mechanics of pesticide movement into ground water. Honeycutt RC, Schadebacker DJ, eds. Ann Arbor, MI: Ann Arbor Press (199 4) 8 Chemicals Inspection and Testing Institute; Biodegradation and bioaccumulation data of existing chemicals based on the CSCL Japan. Japan Chemical Industry Ecology

- Toxicology and Information Center. ISBN 4

- 89074

- 101

- 1 (1992)



### NAA appears to be genera lly short lived and may show mobility in the environment , based on

v alues reported in the open literature or predicted by EPISUITE v.4.1 . It is expected to degrade by means of a combination of both biotic ( e.g. , aerobic soil metabolism) and abiotic ( e.g. , photolysis) processes. Bodies of water adjacent to treated field s may be contaminated through spray drift or runoff. However, it appears that due to its low persistence, only runoff events occurring shortly (within days to a few weeks) after application would affect those bodies of water. Because NAA is mostly ionized in the environment (pKa = 3.50 ), it would partition preferentially to water. Depending on its application method, the presence of NAA may be distributed on various parts of the plant: if applied aerially or by ground conventional methods, it would be expected to be mostly in /on foliage; if applied by hand

- held sprayer and paint brush, NAA would be present in plant tips used for sprout/sucker formation control; finally, if applied diluted t o the soil (root dip or soil drench), it would be present mostly in the roots to stimulate root growth. Since NAA is systemic, it may redistribute through plant tissue.

The environmental fate characteristics of the salts of NAA are expected to be similar to those of the acid. In the environment, it is assumed that the NAA salts will rapidly dissociate to 1

- naphthalene acetate anion and its corresponding cation. Further

, as indicated in the table and as mentioned above, based on its pKa

, NAA is expected to exist mostly as the anion in typical environmental conditions. Anions generally do not adsorb to organic carbon and clay more strongly , compared to their neutral counterparts.

It appears that volatility could be a significant route of dissipation for NAA especially under acidic environmental conditions. Experimental data on a foliar dissipation study shows measured half

- lives of 34.2 h ou r s for NAA, 131.6 h ou r s for 1

- naphthalene

- acetamide, and 12.8 h ou r s for NAA ethyl ester (MRID No. 4 3482101 ). This is consistent with NAA’s relatively high measured vapor pressures (0.3 mmHg ). It is noted, however, that its estimated Henry’s Law Constant is moderate ( 1.75 x 10

- 4 

### ) atm

- m 3 

### /mol because its solubility is high. Abiotic dissipation processes may also contribute to NAA’s rapid dissipation from foliage ( i.e

. , photolysis).

N aphthalene acetic acid, ethyl ester is susceptible to hydrolysis at high pHs. The chemical was stable at pH 5, relatively stable at pH 7 ( its extrapolated half

- life of 26 6 days is well beyond the experimental time frame of 35 days), and showed a half

- life of 7. 4 days at pH 9. This behavior is consistent with the ester moiety of NAA ethyl ester . The product of NAA ethyl ester ’s hydrolysis is NAA.

It appears that NAA in aqueous solution is unstable to sunlight irradiation. Crosby and Tang (1969) report ed the detections of photolysis products 1

- naphthoic and phthalic acids (among others), following exposure of an aqueous solution of NAA to sunlight. All NAA degraded rapidly in 4 days. The data available from Crosby and Tang (1969) is not sufficient to calculate

### 18

an accurate half

- life; however, given that the chemical is fully photolyzed in a period of 4 days, EFED will assume a conservative half

- lif e of 4 days for modeling purposes. According to the HSDB, o n soils, under aerobic conditions, NAA exposure to UV and sunlight produced 1

- hydroxymethyl naphthalene, 1

- naphthaldehyde, naphthalene

- 1

- carboxylic acid

, and 1

- methyl

naphthalene. Only the 1

- meth yl

- naphthalene was observed anaerobically. Phthalic acid has also been observed. No half

- lives were reported in the HSDB regarding the soil photolysis of NAA. Upon exposure to sunlight, gaseous phase NAA reaction with hydroxyl (OH) radicals should
proce ed with a half

- life of around 0.3 days (EPI SUITE estimate).

NAA, and structurally similar compounds such as 1

- methylnaphthalene and ethyl

- naphthalene, are susceptible to biodegradation. For NAA, a half

- life of 10 days was reported in the HSDB, and it was attrib uted to microbial degradation ; however, this study was not available for review by the Agency

. For NAA, EPI SUITE ’s KOCWIN predicts a K OC 

### value of 24.8 L/kg OC 

### . NAA is mobile according to the FAO mobility classification (FAO 2000)

.
Per the HSDB, f

or NAA measured BCFs of only 0.15

- 0.59 and <1.7

- 4.2 were observed in carp ( Cyprinus carpio ) at test chemical concentrations of 0.5 and 0.05 mg/L, respectively. These values suggest a low potential of bioconcentration for NAA. This is consistent with the low K OW 

### for NAA of 174.

There are considerable uncertainties in this problem formulation du e to the lack of measured data. Most of the environmental fate characteristics available for NAA are derived from structure activity relationships or are cited by the HSDB and not available for in

- house review.



## a. Transformation Products

T here is lack of information about possible degradates of NAA. To narrow the gap regarding the data requirements, at the time of the 2007 Reregistration, EFED ran the model CATABOL for NAA. Appendix B ( Table B2 ) shows the potential metabolites of NAA. The model predicts that initially, under metabolism conditions, the first likely process is the loss of one carbon (likely as CO 2 

### ) to yield 1

- methyl

- naphthalene , and subsequently oxid ation to yield 2

- naphthylmethanol, 2

- naphthaldehyde and 2

- naphthoic acid (all three of these compounds are also photodegradates). For the likely degradation sequence, please refer to Table B2 in the appendix . At the present time, EFED cannot confirm the presence of the above mentioned degradates (or any of the ones mentioned in Table B2 )

, under metabolic conditions . Additional information on the metabolism of NAA is being requested to fill the data gap for both NAA and its derivatives

.



# 6. Receptors

Available toxicity data for NAA and associated active ingredients with the most sensitive species within a taxonomic group is presented in Table 6 and Table 7 for aquatic organisms and Table 8 and Table 9 for terr estrial organisms However, a considerable margin of exposure exists for aquatic plants based on the previous ecological risk assessments ( e.g., the 2004 RED assessment;

### 19

D306433), with RQ values of 0.03 and 0.0003 for aquatic macrophytes and green algae,

re spectively. Furthermore, the NAA ester is only applied to the root portion of plants and used in grafting. This type of use pattern is expected to result in very low exposure to the aquatic environment.



## a. Aquatic Organisms

NAA and Associated Salts

. As can be seen in Table 6

, NAA is slightly to practically non

- toxic to freshwater fish and invertebrates on an acute exposure basis, with acute LC 50 

### or EC 50 

### values ranging from 28 to 180 mg ai/L for the TGAI. Available data on a NAA formulation for rainbow trout indicates similar acute toxicity as the TGAI (within a factor of 2). No data are available on the chronic toxicity of NAA or its salts to fish or aquatic invertebrates. For aquatic plants, EC 50 

### values range from 5.1 mg ai/L for duckweed to 14.9 mg ai/L for green algae. Notably, no data have been submitted for other types of algae (bluegreen, saltwater diatom, freshwater diatoms).

Table 6 . Summary of the M ost S ensitive Aquatic Toxicity E ndpoints for Napthalene acetic acid or its salt s

Taxonomic Group Study Type Surrogate Species Chemical (Form) Toxicity

Value Acute Toxicity

Classification (MRID)

Freshwater Fish 1 Acute Rainbow trout, Oncorhynchus mykiss NAA

(98% TGAI) 96

- h LC 50 = 28

mg ai/L Slightly toxic

( 00082528, acceptable)

NAA (15.1% Formulation) 96

- h LC 50 = 14

mg ai/L Slightly Toxic

(00042756; supplemental)

Chronic Data gap 2

Freshwater invertebrates Acute Water flea Daphnia magna NAA

(TGAI) 48

- h EC 50 =

180 mg ai/L Practically Non

toxic ( 00082526 Acceptable )

Chronic Data gap 2

Estuarine/marine fish Acute Data gap 2

Chronic Data gap 2

Estuarine/marine invertebrates Acute Data gap 2

Chronic Data gap 2

Aquatic plants and algae Vascular Duckweed, Lemna gibba Potassium salt

of NAA (24.2% formulation) 14

- d EC 50 =

5.1 mg ai/L NOAEC = 0.46 mg ai/L N/A

(42582202, acceptable)

Non

- vascular Green algae,

Selenastrum capricornutum Ammonium

salt of NAA (21.4% a.i.) EC 50 = 14.9

mg ai/L NOAEC = 6.5 mg ai/L N/A

( 42582203, acceptable)

### 20 1 Freshwater fish may be surrogates for aquatic

- phase amphibians.
2 Previous ecological risk assessments relied on QSAR estimates to characterize uncertainty associated with the lack of toxicity data for these taxa. Since a large margin of exposure existed relative to the estimated toxicity value, toxicity test data were not requested for these taxa.



### NAA Amide and Ester. As seen in Table 7, the available toxicity data indicates that the ester form of NAA is more acutely toxic than the acid form of NAA to aquatic animals compared to the acid form of NAA by up to a facto r of 10. These results are consistent with the findings from the acid and ester forms of other similar compounds. A formulation of the ethyl ester form of NAA was considerably less toxic than the TGAI ( acute EC 50 

### values of 23.8 vs. 5.68 mg ai/L, respecti vely). No data are available on the chronic toxicity of the amide or ester forms of NAA to aquatic animals. Similarly, no data are available on their toxicity to aquatic plants.

Table 7. Summary of the M ost S ensitive Aquatic Toxicity E ndpoints for 1

- n aphthaleneacetamide and Napthalene acetic acid ethyl ester

Taxonomic Group Study Type Surrogate Species Chemical (Form) Toxicity Value Acute Toxicity Classification (MRID)

Freshwater Fish 1 Acute Bluegill sunfish, Lepomis macrochirus NAA ethyl

ester (TGAI) 96

- h LC 50 =

2.68 mg ai/L Moderately toxic

(42498101, acceptable)

Chronic Data gap 2

Freshwater invertebrates Acute Water flea Daphnia magna NAA ethyl ester

(TGAI) 48

- h EC 50 = 5.68

mg ai/L Moderately

Toxic (42470801, In Review)

NAA ethyl ester (Formulation) 48

- h EC 50 = 23.8 mg ai/L Moderately

Toxic ( 00042755

, Supplemental )

Chronic Data gap 2

Estuarine/marine fish Acute Data gap 2

Chronic Data gap 2

Estuarine/marine invertebrates Acute Data gap 2

Chronic Data gap 2

Aquatic plants and algae Vascular Data gap

Non

- vascular Data gap

1 Freshwater fish may be surrogates for aquatic

- phase amphibians.
2 Previous ecological risk assessments relied on QSAR estimates to characterize uncertainty associated with the lack of toxicity data for these taxa. Since a large margin of exposure existed relative to the estimated toxicity value, toxicity test data were not requested for these taxa.

### 21

Consideration of QSAR Information and Data Needs for Aquatic Organisms

. Previous ecological risk assessments have noted a relatively substantial margin of safety between the predicted exposure and measured effect levels fo r the acid and salt forms of NAA. For example, RQ values ranged between 0.0003 and 0.03 for green algae and duckweed based on the 2 004 RED assessment; D306433). For freshwater fish and invertebrates, acute RQ values of 7 x 10

- 5 

### and 4 x 10

- 4 

### were calculat ed. These RQ values are based on estimated peak concentration of 0.012 mg ai/L for NAA. RQ values for the ester form of NAA were not determined due to an assumed lack of a complete exposure pathway (applied for root and bark treatment, only).

Given the lack of chronic toxicity data for NAA and its salts to aquatic animals, the previous RED assessment explored the need for such data by using QSAR

- based estimates of chronic toxicity. Since the QSAR models have since been updated, EFED repeated the QSAR an alysis using ECOSAR v. 1.1, the results of which are shown in Table 8 for the acid, amide and ester forms of NAA.

Table 8. QSAR

- based estimates of the toxicity of NAA (acid, amide and ester) compounds to aquatic organisms (ECOSAR v. 1.1) Species/Endpoint Compound Naphthalene acetic acid (acid) mg/L Naphthaleneacetamide (amide) mg/L Ethyl 1

- naphthaleneacetate (ester) mg/L Meas. Est. Adj. (1) Measured Estimated Measured Estimated FW Fish Acute 96

- h LC 50 28 (RBT 41 (BG) 931 28

--- 110 2.68 2.72

FW Fish Chronic

--- 93.4 2.8

--- 0.15

--- 0.14
SW Fish Acute 96

- h LC 50 --- 1,174 35.3

--- 97

--- 3.7

SW Fish Chronic

--- 148 4.5

--- --- --- 0.73
FW Invert (D. magna ) Acute 48

- h EC 50 180 540 180

--- 147 5.68 4.7

FW Invert ( D. magna ) Chronic --- 56.1 18.7

--- 6.3

--- 1.9 SW Invert (Mysid Shrimp) Acute 96

- h LC 50 --- 742 247

--- 5.4

--- 1.6

SW Invert (Mysid Shrimp) Chronic --- 59.7 19.9

--- --- --- 3.2
Green Algae 96

- h EC 50 14.9 441 NA

--- 3.2

--- 1.5

1 Since QSAR estimates were only available for baseline toxicity ( using neutral organics) , and these estimates did not agree with measured data for NAA (shown in bold ) , QSAR estimated values for NAA were adjusted based on the ratio of the measured to estimated value within each taxonomic group. Adjus tment factors are 0.03 for fish and 0.33 for invertebrates

. RBT = rainbow trout; BG = bluegill sunfish.



### For NAA, the predicted QSAR

- based toxicity values for fish and aquatic invert ebrate s (following adjustment based on measured data) are three to four or ders of magnitude greater than the previously estimated aquatic EEC s (0.01 2

– 0.014 mg ai /L)

. When considering the levels of concern (LOC) for acute and chronic risk to listed species (0.05 and 1.0, respectively), the resulting RQ values are 100X to 1500X below these LOCs for NAA (and by extension, its salts).

### 22

While the aquatic animal database is incomplete for NAA and its salts, these margin s of safety suggest that additional toxicity data for the acid and salt forms of NAA are unlikely to alter the risk assessment conclusions for aquatic animals. Although there is a similar wide margin of safety with the salt form s of NAA with green algae , toxicity data were only submitted for one algal species. Given the mode of action of NAA and sensitivity diffe rences among algal species, toxicity data for the other 3 standard algal species for NAA is considered useful for risk assessment

. Data on NAA can be bridged to its salt forms.

With amide form of NAA, no aquatic toxicity data have been submitted. Unlike with NAA, the difference between the QSAR

- based toxicity values for n aphthaleneacetamide are much closer, in some cases within a factor of 10X ( e.g., chronic value for freshwater fish = 0.15 mg/L vs. chronic EEC of 0.012 mg/L). Furthermore, there are no s ubmitted toxicity data for n aphthaleneacetamide from which to judge the reliability of the QSAR estimates. Therefore, submission of aquatic toxicity data which can be used for assessing risks of naphthaleneacetamide is considered to be of value for the fo rthcoming ecological risk assessment. In absence of such data, EFED is proposing to bridge results from similarly structured compounds of the same mode of action ( e.g., Quinclorac and Quinmerac)

. For the ester form of NAA, usage information suggest a limited exposure pathway exists (e.g., direct application to bark and plant roots). Therefore, additional information for NAA ethyl ester is not considered necessary for the forthcoming aquatic risk a ssessment.



## b. Terrestrial Organisms

With birds, NAA and related compounds are slightly toxic to birds on an acute oral basis and practically non

- toxic to birds on an acute dietary basis ( Tables 8 and 9 ). No chronic avian reproductio n studies are available on birds. Based on the maximum single application rate of NAA (0.22 lb ai/A), a peak concentration of approximately 50 ppm is predicted on short grass using T

- REX version 1.5.1. Thus, an avian reproductive NOAEC of 50 ppm or lower would trigger risk concerns to listed species of birds consuming short grass (based on a chronic risk LOC of 1.0). Chronic avian toxicity data is considered valuable for the forthcoming ecological risk assessment.

With an acute oral LD 50 

### of 933 mg ai/kg

- bw report for the rat, NAA TGAI is classified as slightly toxic on an acute basis to mammals. Chronic dietary exposure of rats to NAA sodium salt over two generations resulted in a NOAEC of 210 mg ai/kg

- diet

. No toxicity data for the hon ey bee has been submitted to the Agency for any of the NAA salts

, acid, amide or ester . Without toxicity information for pollinator insects this portion of the assessment cannot be conducted. Therefore, EPA is requesting additional data on the toxicity of NAA to the honey bee according to the recent OPP bee risk assessment guidance 6



### .

6 http://www.epa.gov/pesticides/science/efed/policy_guidance/team_authors/terrestrial_biology_tech_team/GuidanceA ssessingPesticideRisk2Bees.pdf

### 23

Terrestrial plant toxicity testing has been submitted for the potassium and sodium salts of NAA. No terrestrial plant data has been submitted for products containing the amide or ester forms of NAA. Exposure of terrestrial plants to the NAA ester is expected to be negligible due to its limited use pattern

. Unlike the ester form of NAA, exposure is expected for the amide form of NAA. Therefore, submission of toxicity dat a that can be used to assess the effect of naphthaleneacetamide on terrestrial plants is recommended

.

Table 8 . Summary of the M ost S ensitive E ndpoints from T errestrial T oxicity S tudies for Napthalene acetic acid and associated salts Taxonomic Group Study Type Surrogate Species Chemical

(form) Toxicity Value Acute Toxicity Classification (MRID)

Birds 1 Acute oral Mallard duck, Anas platyrhynchos NAA (TGAI,

97%) LD 50 = 1750 mg

ai/kg

- bw Slightly toxic

(00065839, supplemental)

NAA (Formulation, 15.1%) LD 50 > 2,150 mg

ai/kg

- bw Practically non

toxic (00042754, Supplemental)

Sub

- acute dietary Bobwhite quail

,

Colinus virginianus NAA (TGAI) 8

- d LC 50 >10,000 mg ai/kg

diet Practically non

toxic ( 00085909

, supplemental)

NAA (Formulation, 15.1%) 8

- d LC 50

>10,000 mg ai/kg

diet Practically non

toxic ( 42584202

, acceptable)
Chronic Bobwhite quail

or Mallard duck Data gap

Mammals Acute Oral Laboratory rat ( Rattus norvegicus ) NAA (TGAI)

LD 50 = 933 mg/Kg LD 50 = 933 mg

ai/kg

- bw Slightly toxic

(00108829, acceptable)

Chronic Laboratory rat

( Rattus norvegicus ) NAA sodium

salt (TGAI) 2

- generation

NOAEC = 210 mg ai/kg

- diet (reduced litter survival & pup weight) N/A

(43796301, acceptable)

Insects Acute contact Honey bee Apis mellifera Data gap

Terrestrial plants Seedling

Emergence Dicot

– Carrot NAA ammonium salt (formulation) EC 25 = 0.015 lb

ai/A NOAEC = 0.011 lb ai/A 43803201

Monocot

– wheat NAA Potassium

salt (formulation) EC 25 = 0.075 lb

ai/A NOAEC = 0.02 lb ai/A 43803201

Terrestrial plants Vegetative

vigor Dicot

– Tomato NAA Potassium salt (formulation) EC 25 = 0.043 lb

ae/A NOAEC = 0.01 lb ai/A 43141101

### 24 Taxonomic

Group Study Type Surrogate Species Chemical

(form) Toxicity Value Acute Toxicity Classification (MRID)
Monocot

– all species tested NAA

ammonium salt EC25 >0.1 lb ai/A 42564201

1 Toxicity data for b irds are used as surrogates for terrestria l

- phase amphibians and reptiles in the absence of data for these taxa.



### Table 9 . Summary of the M ost S ensitive E ndpoints from T errestrial T oxicity S tudies for the amide and ester forms of NAA Taxonomic Group Study Type Surrogate Species Chemical

(form) Toxicity Value Acute Toxicity Classification (MRID)

Birds 1 Acute oral Data Gap

Sub

- acute dietary Bobwhite quail

,

Colinus virginianus NAA ethyl ester

(TGAI) 8

- d LC 50

>5,620 mg ai/kg

- diet Practically non

toxic ( 42584202

, acceptable)

NAA amide (TGAI) 8

- d LC 50

>5,620 mg ai/kg

- diet Practically non

toxic ( 4258420 1, acceptable)

Chronic Bobwhite quail

or Mallard duck Data gap

Mammals Acute Oral Laboratory rat ( Rattus norvegicus ) NAA ethyl ester

(TGAI) LD 50 = 2,186

mg ai/kg

- bw Slightly toxic

(43494101, acceptable)

NAA amide (TGAI) LD 50 > 5,000

mg ai/kg

- bw Practically non

toxic (43495901, acceptable)
Chronic Data Gap

Insects Acute contact Honey bee Apis mellifera Data gap

Terrestrial plants Seedling

Emergence Dicots Data gap

Monocots Data gap

Terrestrial plants Vegetative vigor Dicots Data gap

Monocots Data gap



## c. Ecological Incidents

The ecological incident information system (EIIS) is an OPP database that houses ecological incidents that have been reported to the Agency. When available, EIIS includes date and location of an incident, type and magnitude of effects observed in various species, use(s) of pesticides known or suspected of contributing to the incident, and results of any chemical residue analysis or other analyses conducted during incident investigation. EIIS incidents are categorized according

### 25

to the certainty that the in cident resulted from pesticide exposure. The Avian Monitoring System (AIMS) is a database administered by the American Bird Conservancy that contains publicly available data on reported avian incidents involving pesticides. Many of the incidents listed i n this database are also in the EIIS

. EIIS returned a single incident (IO25475

- 001) with sodium

- 1

- napth alene acetate 7 

### involving plant damage from a ground application of Fruitone in Wayne County, NY on apples . Plant damage in the form of speckling of leaves and thinning of fruit was reported. Closer inspection of the incident report showed that the plant growth regulator was applied along with 8 other actives including insecticides and fungicides. No certainty was assigned to any of the actives involv ed in this incident.



# 7. Exposure Pathways of Concern

The environmental fate properties and use patterns of certain ground broadcast or aerially applied

n apthalene acetic acid

, its sodium, ammonium, and potassium salts , and the amide indicate that direct spra y, spray drift, and runoff represent potential transport mechanisms to aquatic and terrestrial organisms.

Terrestrial Organisms (NAA, salts, and amide)

– Direct exposure to residues during application either dermally or via inhalation of spray droplets

– Exposure to applied residues on foliar surfaces through dermal contact

– Systemic adsorption by plants of residues through roots or foliar surfaces or from seed uses

– Dietary exposure through feeding on vegetation or insects that have been exposed during appl ication of NAA products either directly or via off target spray drift or to treated seed.

– Ingestion of residues through drinking water sources such as puddles, irrigation ditches, canals, contaminated irrigation water or dew within or adjacent to the appl ication site.

Aquatic or Semi Aquatic Organisms (NAA, salts, and amide)

– Exposure via water which has received direct spray drift

– Dermal exposure from spray drift into littoral areas (semi aquatic plants, amphibians and semi aquatic insects, and reptiles) near application sites

– Exposure to residues resulting from runoff originating on treated areas.

– Dietary ingestion of aquatic or semi aquatic plant tissues that have systemically adsorbed NAA residues.

Drinking water and inhalation exposure pathways were screened using the SIP (Screening Imbibition Program) and STIR (Screening Tool for Inhalation Risk) screening methods and were found to be exposure pathways of low concern (no LOC exceedances are expected). SIP and STIR are described in detail at: http://www.epa.gov/oppefed1/models/terrestrial/index.htm

.

7 PC code 056007

### 26 

# 8. Analysis Plan

a. Stressors of Concern

i. Ecological Risk Assessment

Pending the receipt and analysis of additional fate data, the major stressor of concern for terrestrial and aquatic organisms are considered to be NAA and naphthaleneacetamide . Based on its low pKa value, NAA is expected to dissociate to the anion ic form in natural environments. The sodium, potassium and ammonium salts of NAA are also expected to dissociate to the anion

. Therefore, toxicity and fate data for NAA and its salts are considered to be similar and will be used interchangeably. Although e thyl 1

- naphthaleneacetate has greater toxicity than the other forms of NAA, the current use pattern for the ethyl ester is expected to result in negligible exposure to non

- target organisms.

No toxicity data have been submitted for the NAA degradates. When EFED receives the new fate studies being requested as part of this problem formulation, it will evaluate the possible toxicity of NAA degradates based on structure activity relationships (ECOSAR). If, based on SAR

, it is found that o ne or more degradates are of concern, they will be evaluated using the total toxic residue method (TTR), adjusting for differential toxicity if necessary. Using the TTR approach the half

- lives for the decay of parent compound plus the degradates of concer n are calculated. The aquatic modeling is performed with the TTR half

- lives.

ii. Drinking Water

The drinking water assessments conducted to support the registration review human health risk

assess ments of Napthalene acetic acid and related compounds will i ncorporate model estimates of NAA and naphthaleneacetamide , pending review of additional fate and toxicity information on the degradates.

Because the FIFRA data requirements established in 40 CFR §158 are not fulfilled for any one active ingredient among the registered acid , acetamide, ethyl ester, and salts for NAA, the Agency will use data from open literature sources, other governmental sources, and when necessary

, predictive toxicological models that rely on structural characteristics

. , such as ECOSAR (for aquatic organisms)

.



## b. Measures of Exposure

EFED will use standard available models to evaluate potential exposures to aquatic and terrestrial organisms as described at http://www.epa.gov/pesticides/science/models_db.htm

. Estimates of residue levels on terrestrial surfaces for this chemical will be produced through use of T

- REX modeling. The more conservative scenario will be selected for use i n the characterization of risk to terrestrial organisms. Monitoring data from previously registered uses of NAA will be considered in characterizing expected levels of exposure for terrestrial organisms.

### 27

Estimates of surface and groundwater monitoring ex posure levels will be modeled for Napthalene acetic acid using the latest Surface Waters Concentration Calculator (SWCC) (PRZM/VVWM) modeling for scenarios determined to be of the highest concern. Groundwater exposure potential will be modeled using the l atest version of the SCI

- GROW and PRZM

- GW models. Nationwide monitoring programs will also be consulted for data regarding Napthalene acetic acid detections in surface or groundwater.

The Agency is not aware of any monitoring conducted by federal and sta te agencies on NAA and its associated compounds . Any available monitoring data will be considered in the assessment to the extent that data on NAA is available.



## c. Measures of Effect

Toxicity data presented in Section 6 of this problem formulation will be used to calculate risk quotients. Any additional information submitted by the registrant or found in the open literature prior to conduct of the risk assessment will also be considered. The open literature studies are identified using EPA’s ECOTOXicology database ( ECOTOX) ( USEPA, 2007 c ), which employs a literature search engine for locating chemical toxicity data for aquatic life, terrestrial plants, and wildlife. The evaluation of both sources of data can also provid e insight into the direct and indirect effects of pesticides on biotic communities from loss of species that are sensitive to the chemical s and from changes in structure and functional characteristic s of the affected communities.



## 9. Endangered Species Assessments

Consistent with the Agency’s responsibility under the Endangered Species Act (ESA), the Agency will evaluate risks to federally listed threatened and/or endangered (listed) species from registered uses of pesticides in registration review . The process for evaluating potential risks to listed species is further described at http://www.epa.gov/oppfead1/endanger/litstatus/riskasses.htm

.



## 10. Endocrine Disruptor Screening Program

Napthalene acetic acid actives are not among the group of 58 pesticide active ingredients on the initial list to be screened under the EDSP. Under FFDCA sec. 408(p) the Agency must screen all pesticide chemicals. Accordingly, EPA anticipates is suing future EDSP test orders/data call

- ins for all pesticide active ingredients

. Additional details are provided in the appendices of this document.

For further information on the status of the EDSP, the policies and procedures, the list of 67 chemicals (actives and inerts) , the test guidelines and the Tier 1 screening battery, please visit our website: http://www.epa.gov/endo/

.

### 28 

## 11. Preliminary Identification of Data Gaps

a. Environmental Fate

P h ysical and Chemical Properties: Dissociation Constants for NAA Derivative s : Sodium Salt, Potassium Salt, Ammonium Salt, Ethyl Ester and Acetamide. The registrant is requested to provide this important data for naphthaleneacetic acid (NAA), and for the salts, ethyl ester and acetamide . In this respect

, accuracy of the physical and chemical data contained in this document ( e.g. , the solubility) , which were obtained from sources other than submitted/accepted studies needs to be verified, for the salts, ethyl ester and acetamide . Based on the general properties available to the Agency, it is believed that the salts will dissociate rapidly to the naphthalene acetate anion and the corresponding cation. Based upon the available hydrolysis study, it is apparent that under typical e nvironmental conditions (at pH 7), the ethyl ester and the acetamide do not dissociate.

Table s 10 a and 10b identi f y available environmental fate studies for each guideline requirement, as well as study classifications and whether or not further data are needed in order to support risk
assessment.

Table 10 a . Submitted Environmental Fate Data for Napthaleneacetic acid (NAA) and its salts

OCSPP Data

Requirement Submitted

Studies (MRID) Study

Classifications Are data

needed to conduct risk assessment? Justification and Assumptions EPA

will Make in Absence of Data

835.2120 Hydrolysis 00 129382 Acceptable No The study was conducted on NAA, the ethyl ester and the acetamide. 835.2240 Aqueous

photolysis Crosby and

Tang (1969), 4943, 49298203, 49298303 In review

Unacceptable Waiver request No NAA appears to degrade rapidly when irradiated with natural sunlight. Four days of sunlight exposure converted NAA completely to o

- phthalic acid and a small amount of 1

- naphthoic acid. NAA appears to degrade completely in 4 days , but a half

- life could not be derived from data in the study . In the absence of additional information, EFED will assume a photolytic half

- life of

~ 4 days. 835.2410 Soil photolysis 49298203, 49298303 Waiver request No

--

835.2370 Air photolysis 49298203, 49298303 Waiver request No t 1/2 = 0.289 days due to hydroxyl radical reactions.

### 29

OCSPP Data

Requirement Submitted

Studies (MRID) Study

Classifications Are data

needed to conduct risk assessment? Justification and Assumptions EPA

will Make in Absence of Data

835.4100 Aerobic soil

metabolism 4943,

49298203, 49298303 Unacceptable

Waiver request Yes At the present time, EFED is requesting a study to be conducted with naphthalene acetic acid (two so ils)

. No data w ere submitted on dissociation of the acid der ivatives ; the requested stud ies are based on the assumption that the sodium, potassium and ammonium salts of this chemical ar e highly soluble and dissociate completely to the acid. If this is not the case

, then on e additional study is requested for one of the salts

. In the absence of data, the Agency will assume that NAA and derivatives are
st able to aerobic soil metabolism. 835.4200 Anaerobic soil

metabolism 49298203,

49298303 Waiver request No

--

835.4300 Aerobic aquatic

metabolism 49298203,

49298303 Waiver request Yes At the present time, EFED is requesting a study to be conducted with naphthalene acetic acid in two sediment systems. No data ha ve been identified on the dissociation of the acid derivatives and the requested studies are based on the assumption that the

s odium, potassium and ammonium salts of this chemical are highly soluble and dissociate completely to naphthalene
acetate . If this is not the case

, then an additional study is requested for one of the salts. 1

In the absence of data, the Agency will

assume that NAA is stable to aerobic aquatic metabolism. 835.4400 Anaerobic

aquatic metabolism 49298203,

49298303 Waiver request No

--

835.1230 835.1240 Adsorption/

desorption and leaching 49298203,

49298303 Waiver request Yes At the present time, EFED is requesting a study to be conducted with naphthalene acetic acid (two soils and a sediment)

. 2

In the absence of data, conservative assumptions will be made for NAA. 835.1410 Volatility

–

laboratory 49298203,

49298303 Waiver request No

--

### 30

OCSPP Data

Requirement Submitted

Studies (MRID) Study

Classifications Are data

needed to conduct risk assessment? Justification and Assumptions EPA

will Make in Absence of Data

835.6100 Terrestrial field

dissipation 49298203,

49298303 Waiver request No

--

850.6100 Analytical

method in soil Not available N/A No

--

835.8100 Field volatility 49298203, 49298303 Waiver request No

--

835.6200 Aquatic field

dissipation 49298203 Waiver request No

--

850.6100 Analytical

method in water Not available N/A Yes An Environmental Chemistry Method and associated Independent Laboratory Validation for the analysis of NAA (and degradates of ecological and/ or human health concern), in water is required. 835.7100 Groundwater

monitoring 49298203,

49298303 Waiver request No

--

850.1730 Fish BCF Not available N/A No Waiver was granted in the RED due to NAA’s low predicted K OW
. 1 The Agency is aware that an aerobic aquatic metabolism study is available for the acid in two sediment systems. The study was submitted to the EU. According to the EU Draft Assessment Report, the DT 50 ’s for the total system in two sediments are 6.2 and 9.5 days. Should it comply with Agency guidance, this study could be submitted to the Agency. If found acceptable or supplemental, it may be used in the Preliminary Risk Assessment.
2 The Agency is aware that a batch equilibrium study is available for th e acid, conducted in three soils, and submitted to the EU. According to the EU Draft Assessment Report, naphthalene acetic acid’s K d values range from 0.40

- 2.72

cm 3 /g, K OC s range from 68.5

- 138 cm 3 /g OC , K F values range from 0.297

- 1.77 cm 3 /g, and K FOC s rang e from 50.3

- 88.5

cm 3 /g OC
. Should it comply with Agency guidance, this study c ould be submitted to the Agency. If it is found to be acceptable or supplemental, it may be used in th e Preliminary Risk Assessment.



### Table 10 . Submitted Environmental Fate Data for Napthalene acet amide

OCSPP Guideline Data

Requirement Submitted

Studies (MRID) Study

Classifications Are data

needed to conduct risk assessment? Justification and Assumptions EPA

will Make in Absence of Data

835.2120 Hydrolysis 00 129382 Acceptable No The study was conducted on NAA, the ethyl ester and the acetamide. 835.2240 Aqueous

photolysis 4943,

49298203, 49298303 Unacceptable

Waiver request No

--

835.2410 Soil photolysis 49298203, 49298303 Waiver request No

--

835.2370 Air photolysis 49298203, 49298303 Waiver request No

--

### 31

OCSPP Guideline Data

Requirement Submitted

Studies (MRID) Study

Classifications Are data

needed to conduct risk assessment? Justification and Assumptions EPA

will Make in Absence of Data

835.4100 Aerobic soil

metabolism 4943,

49298203, 49298303 Unacceptable

Waiver request Yes At the present time, EFED is requesting a study to be conducted with naphthalene acetamide (in two soils).

In the absence of data, the Agency will assume that NAA and derivatives are stable to aerobic soil metabolism. 835.4200 Anaerobic soil

metabolism 49298203,

49298303 Waiver request No

--

835.4300 Aerobic aquatic

metabolism 49298203,

49298303 Waiver request Yes At the present time, EFED is requesting a study to be conducted with naphthalene acetamide deriv ative in two sediment systems

. In the absence of data, the Agency will assume that NAA is stable to aerobic aquatic metabolism. 835.4400 Anaerobic

aquatic
met abolism 49298203,

49298303 Waiver request No

--

835.1230 835.1240 Adsorption/

desorption and leaching 49298203,

49298303 Waiver request Yes At the present time, EFED is requesting a study to be conducted with naphthalene acetamide derivative (two soils and a sediment )

.
In the absence of data, conservative assumptions will be made for NAA. 835.1410 Volatility

–

laboratory 49298203,

49298303 Waiver request No

--

835.6100 Terrestrial field

dissipation 49298203,

49298303 Waiver request No

--

850.6100 Analytical

method in soil Not available N/A No

--

835.8100 Field volatility 49298203, 49298303 Waiver request No

--

835.6200 Aquatic field

dissipation 49298203 Waiver request No

--

850.6100 Analytical

method in water Not available N/A Yes An Environmental Chemistry Method and associated Independent Laboratory Validation for the analysis of naphthalene acetamide derivative (and degradates of ecological and/or human health concern), in water is required. 835.7100 Groundwater

monitoring 49298203

,

49298303 Waiver request No

--

850.1730 Fish BCF Not available N/A No

--

### 32 

## b. Effects

For addressing the previously identified gaps in the ecological effects database for NAA and associated compounds, the following bridging strategy is being proposed in order to make maximum use of available information (see Table 10 )

. Aquatic Animals: For aquatic animals, toxicity data are being requested for Napthalene
acet amide 

### , since no data have been submitted and the margin of safety between exposure and toxicity is relatively small (within 10X) based on QSAR model predictions. For freshwater fish and invertebrates, both acute and chronic toxicity data are being requested. For saltwater fish and invertebrates, only acute toxicity data are being requested because c hronic toxicity can be estimated using the acute

- to

- chronic ratio (ACR) from the freshwater test species.

Aquatic Plants . Since data are only available for one species of aquatic algae, additional test data are being requested with NAA (salt or acid) f or the remaining three algal species (freshwater diatom, saltwater diatom, cyanobacteria). For NAA amide, the entire suite of vascular and algal toxicity data are being requested.

Table 10

. Submitted A quatic E cological E ffects D ata for Napthalene acetic acid , Napthalene acet amide , and its salts.

OCSPP Guideline Data

Requirement Submitted Studies

(MRID) Study

Classi fication Data needed

for Risk assessment? Comments

-

assumptions

850.1010 Freshwater

invertebrate acute toxicity 00082526

- DM 1

with NAA Acceptable Yes 2 Amide form of NAA, see Note 2.

42470801

- DM with NAA

- ester In

- review

00042755

- DM with NAA ester formulation Supplemental

850.1025 850.1035 850.1045 850.1055 Saltwater

invertebrate acute toxicity No data submitted Yes 2 Amide form of NAA, see Note 2.

850.1075 Freshwater fish

acute toxicity 00082527

- BG with

NAA Acceptable Yes 2 Amide form of NAA, see Note 2.

00082528

- RBT with NAA Acceptable

00042756 with RBT with NAA formulation Acceptable

00042757 with BG with NAA formulation Supplemental

TN 646 with BG with ammonium salt formulation Supplemental

### 33 OCSPP

Guideline Data

Requirement Submitted Studies

(MRID) Study

Classi fication Data needed

for Risk assessment? Comments

-

assumptions

TN 723 with RBT with ammonium salt formulation Supplemental

42498101

- BG with NAA ester technical Acceptable

850.1075 Saltwater fish

acute toxicity No data submitted Yes 2 Amide form of NAA,

s ee Note 2.

850.1300 Freshwater

invertebrate life cycle No data submitted Yes 3 Amide form of NAA,

s ee Note 3.

850.1350 Saltwater

invertebrates life cycle No data submitted Yes 3 Amide form of NAA, see Note 3.

850.1400 Freshwater fish

early

- life stage No data submitted Yes 3 Amide form of NAA, see Note 3.

850.1400 Saltwater fish

early

- life stage No data submitted Yes 3 Amide form of NAA, see Note 3.

850.1500 Fish life cycle No data submitted No

850.4400 Aquatic

vascular plant 42582202 with

potassium salt formulation Acceptable Yes Vascular plant testing requested with the amide form of NAA.

42582204 with ammonium salt formulation Acceptable

850.4500 850.4550 Algal toxicity 42582201 with potassium salt formulation Acceptable

Yes Algal toxicity testing requested with NAA (3 species) and the amide form of NAA (4 species) 42582203 with ammonium salt formulation Acceptable

1 DM= Daphnia magna, BG= Bluegill sunfish and RBT= Rainbow trout 2 Acute toxicity data is needed for risk assessment of the amide form of NAA. 

### In absence of data, EFED will rely on data from the ester form of NAA or similarly structured compounds within the same mode o f action ( e.g., Quinclorac and Quinmerac) 3 Chronic toxicity data is needed for risk assessment of the amide form of NAA. 

### In absence of data, EFED will rely on data from similarly structured compounds within the same mode of action ( e.g., Quinclorac and Quinmerac)

### 34

Birds. For avian species, no acute oral or dietary toxicity data are being requested since results of current toxicity tests with the acid, ester and amide forms of NAA indicate very low acute toxicity. This, in combination with the relativel y low application rate, suggests the receipt of additional data will likely be of low value to the forthcoming risk assessment. No data have been submitted on the chronic toxicity of NAA or its derivatives to birds

. Chronic avian reproduction data for a s imilarly structured compound with the same mode of action (quinclorac; NOAEC = 500

- 1000 ppm ; MRID 44084501 & 44129201 ) in addition to that for other synthetic auxins (aminopyralid, dicamba; NOAEC = 800

- 2600 ppm) suggest low chronic toxicity to birds. Gi ven that a predicted EEC of 50 ppm is expected on avian dietary items (short grass), additional chronic toxicity data for NAA and its derivatives is considered of low value. In absence of data, EFED will bridge chronic toxicity for birds using data from s imilar compounds.

Bees. No data have been submitted on the toxicity of NAA or associated compounds to bees. Since NAA and associated compounds are systemic in plants, exposure of bees to these products is expected through both contact and oral routes o f exposure

. Data are therefore requested for Tier 1 laboratory toxicity studies for bees. These tests include acute toxicity of adult bees (oral and
contact ), acute toxicity to larval bees , and chronic toxicity for adult and larval bees. The amide form of NAA is preferred and can be bridged to NAA and/or its salts.

Terrestrial Pants. Terrestrial plant toxicity testing has been submitted for the potassium and sodium salts of NAA. No terrestrial plant data have been submitted for products containing the amide or ester forms of NAA. Exposure of terrestrial plants to the NAA ester is expected to be negligible due to its limited use pattern. Unlike the ester form of NAA, exposure is expected for the amide form of NAA. Therefore, submission o f toxicity data that can be used to assess the effect of naphthaleneacetamide on terrestrial plants is recommended

.

Table 10

. Submitted Terrestrial E cological E ffects D ata for Napthalene acetic acid and its derivatives

OCSPP Guideline Data

Requirement Submitted

Studies (MRID) Study

Classi fication Data needed

for Risk Assessment ? Comments

850.2100 Avian oral

toxicity 00065839 w

MAL 1 with NAA Acceptable No No additional acute avian toxicity data are being requested due the low acute oral and dietary toxicity to birds 00065840 w BWQ with NAA Supplemental

00042754 w MAL with NAA formulation Supplemental

00042753 w BWQ with NAA formulation Supplemental

850.2 2 00 Avian dietary

toxicity 42584201 w

BWQ with NAA amide Acceptable No

00079520 w MAL with NAA Supplemental

### 35 OCSPP

Guideline Data

Requirement Submitted

Studies (MRID) Study

Classi fication Data needed

for Risk Assessment ? Comments

00085909 w BWQ with NAA formulation Supplemental

00072749 w BWQ with NAA
ester formulation Acceptable

00083052 w MAL with NAA formulation Supplemental

42584202 with BWQ with NAA
ester Acceptable

850.2300 Avian

reproduction No data

submitted Yes 2 See Note 2

850.3020 Honey bee acute

contact toxicity (adults) No data

submitted Yes NAA and associated compounds are systemic and exposure is expected to insect pollinators OECD 213 Honey bee acute

oral toxicity (adults) No data

submitted Yes

OECD 234 Honey bee acute

larval toxicity No data

submitted Yes

Special Study Honey bee

chronic larval toxicity No data

submitted Yes

Special Study Honey bee

chronic adult toxicity (10

- d) No data

submitted Yes

850.3030 Honey bee

residue on foliage No data

submitted Conditional Data may be required pending results of acute contact testing


### OECD 75 8 

### and Oomen et al . 1992 9 Tier 2 semi

- field

testing for pollinators No data

submitted Conditional Data may be required pending results of acute and chronic contact/oral testing

850.3040 Tier 3 full field

testing for pollinators No data

submitted Conditional Data may be required pending results of lower Tier testing

8 OECD. 2007. Guidance document on the honey bee ( Apis mellifera L.) brood test under semi

- field conditions. Series on Testing and Assessment No. 75. ENV/JM/MONO(2007)22.

9 Oomen, P. A. A. DeRuijter and J. Van der Steen. 1992. Method for honey bee brood feeding tests with insect growth

- regulating insecticides. Bul OEPP /EPPO Bulletin 22: 613

– 616.

### 36 OCSPP

Guideline Data

Requirement Submitted

Studies (MRID) Study

Classi fication Data needed

for Risk Assessment ? Comments

850.4100 S eedling

E mergence and Seedling Growth 05012526 with

NAA amide Open lit. Yes (amide form of NAA) Phytotoxicity of

herbicides from root adsorption, Hilton, H.W. 1964

42584203 with K+ salt formulation Invalid K

- Salt Fruit Fix 800

- 24.2% ai

42589901 with NH4+ salt formulation Invalid for SE Tier I with K

Salt Fruit Fix 800

- 24.2% ai

43837401 with K+ salt formulation Acceptable 24.79 % ai Soil drench application only

43803201 with NH4+ salt formulation Acceptable NAA ammonium salt 800g/Gal formulation

05007255 with NAA Open lit. Open literature on phytotoxicity (Hilton, H.W., 1964)

42564203 with K+ salt formulation Acceptable Seed Germination Seedling Emergence

- invalid

850.4150 V egetative V igor 43141101 with K+ salt formulation Yes Yes (amide form of NAA) Tier 2 with K

Salt Fruit Fix 800

- 24.2% ai

42564201with NH4+ salt formulation Acceptable Fruit Fix Super Concentrate 800 21.4% ai

42564202with with K+ salt formulation Supplemental Tier 1 K

- Salt Fruit Fix 24.2 % ai tested

43168301with NH4+ salt formulation Acceptable Fruit Fix Super Concentrate 800 21.4% ai

43168101with with K+ salt formulation Supplemental Carrot only with K

- Salt Fruit Fix 800

- 24.2% ai
1 

### MAL = Mallard duck and BWQ= Bobwhite quail
2 Chronic avian toxicity data is needed for risk assessment of the amide form of NAA. 

### In absence of data, EFED will rely on data from similarly structured compounds within the same mode of action ( e.g., Quinclorac and Quinmerac)

### 37

Justification Tables
Non

- guideline: P h ysical and Chemical Properties: Dissociation Constants for N aphthalene Acetic Acid Derivative Compounds: Sodium Salt, Potassium Salt, Ammonium Salt, Ethyl Ester and Acetamide Rationale for Requiring the Data 

### The Agency does not have dissociation constants for naphthalene acetic acid derivative compounds. The registrant is requested to provide this important data for the acid and each of its derivatives separately. Based on the general properties available to the Agency, it is believed that the salts will dissociate rapidly to the naphthalene acetate anion and their corresponding cation. Based upon the hydrolysis study, it is believed that under typical environmental conditions (pH 7), the ethyl ester and the acetamide do not dissociate. Confirmation of this behavior is required. Practical Utility of the Data How will the data be used? 

### This data would be needed to confirm the suspected behavior of naphthalene acetic acid and its derivative compounds.

How could the data change the Agency’s decision or impact the Agency’s future decision

- making? 

### The data would be used in risk characterization and could change the conclusions regarding the environmental fate behavior of naphthalene acetic acid derivativ e compounds.

Guideline Number: 

### 850. 3020 Study Title: Honey bee Acute Contact tox ic i ty with 

### 1

- naphthaleneacetic acid Rationale for Requiring the Data 

### The Agency currently has no submitted data with which to assess the risk to beneficial pollinator insects from direct contact with applied residues. This study is required for outdoor uses under current FIFRA regulations 40 CFR Part 158.630 Practical Utility of the Data How will the data be used? 

### This data would be needed in order to offer guidance on protective label language for pollinators should there be a need for such protective measures

.

How could the data change the Agency’s decision or impact the Agency’s future decision

- making? 

### The dat a would be used in risk characterization and could change the conclusions of that
assessment if toxicity is indicated to be at hazardous levels of concern.

### 38

Guideline Number: OECD 213 Study Title: Honey bee Acute Oral toxicity with 

### 1

- naphthaleneacetic acid Rationale for Requiring the Data 

### The Agency currently has no submitted data with which to assess the risk to beneficial pollinator insects from oral ingestion. NAA actives are systemically adsorbed into plant tissues and may bees may be exposed through ingestion of pollen and/or nectar containing NAA residues Practical Utility of the Data How will the data be used? 

### This data would be needed in order to offer guidance on protective language for pollinators should th ere be a need for such protective measures

.
How could the data change the Agency’s decision or impact the Agency’s future decision

- making? 

### The data would be used in quantitative risk assessment and could change the conclusions of that assessment if toxicity is indicated to be at hazardous levels of concern.

Guideline Number: Special study Study Title: Honey bee 10 day Adult chronic toxicity test with 

### 1

- naphthaleneacetic acid Rationale for Requiring the Data 

### The Agency currently has no submitted data with which to assess the risk to beneficial pollinator insects from long term oral ingestion. NAA actives are systemically adsorbed into plant tissues and potentially pollen and bees may feed on the pollen over extended periods and repeated visits
to flowering plants. Practical Utility of the Data How will the data be used? 

### This data would be needed in order to offer guidance on protective language for pollinators should there be a need for such protective measures

.
How could the data change the Agency’s decision or impact the Agency’s future decision

- making? 

### The data would be used in risk characterization and could change the conclusions of that assessment if toxicity is indicated to be at hazardous levels of conce rn.

Guideline Number: Special study Study Title: Honey bee 21 Day larval toxicity test with 

### 1

- naphthaleneacetic acid Rationale for Requiring the Data 

### The Agency currently has no submitted data with which to assess the risk to beneficial pollinator larvae from ingestion of brood food or royal jelly containing NAA residues. NAA actives are systemically adsorbed into plant tissues and potentially pollen which may be transported back to hives by foraging adults Practical Utility of the Data How will the data be used? 

### This data would be needed in order to offer guidance on protective language for pollinators should there be a need for such protective measures

. How could the data change the Agency’s decision or impact the Agency’s future decision

- makin g? 

### The data would be used in risk characterization and could change the conclusions of that assessment if toxicity is indicated to be at hazardous levels of concern for honey bee larvae.

### 39

Guideline Number: 850.4400 Study Title : Aquatic Plant Toxicity testing with Freshwater Diatom, Freshwater Blue

- green algae, and Marine diatom with technical 

### 1

- naphthaleneacetic acid and Napthaleneacetamide Rationale for Requiring the Data 

### The Agency currently has limited data with which to assess the risk to non

- target aquatic plants. Only a single species has been tested with a 24.2% ai end use product (K

- Salt Fruit Fix 800). NAA products may be ground and aerially applied to orchards creating potential for drift to adj acent aquatic habitats and exposure of aquatic plants within these areas. Practical Utility of the Data How will the data be used? 

### This data would be needed in order to offer guidance on protective language for non

- target aquatic plants should there be a need for such protective measures

. How could the data change the Agency’s decision or impact the Agency’s future decision

- making? 

### The data would be used in risk characterization and could change the conclusions of that assessment if toxicity is indicat ed to be at hazardous levels of concern for non

- target aquatic plants

.

Guideline Number: 850.1035: 850.105 5 Study Title: Acute Toxicity to Fresh and Saltwater Invertebrates using TGAI Napthaleneacetamide Rationale for Requiring the Data 

### For freshwater and saltwater invertebrates, toxicity data are being requested for the amide form of NAA, since no data have been submitted and the margin of safety between exposure and toxicity is sufficiently narrow based on QSAR model predictions. Practical Utility of the Data How will the data be used? 

### This data would be needed in order to offer guidance on protective language freshwater and estuarine organisms from the NAA amide should there be a need for such protective measures

. How could the data change the Agency’s decision or impact the Agency’s future decision

- making? 

### The data would be used in risk characterization and could change the conclusions of that assessment if toxicity is indicated to be at hazardous levels to these organisms

.

Guideline Number: 850.1075 Study Title: Acute Toxicity to Fresh and Saltwater Fish using TGAI Napthaleneacetamide Rationale for Requiring the Data 

### For freshwater and saltwater fish, toxicity data are being requested for the amide form of NAA, since no data have been submitted and the margin of safety between exposure and toxicity is sufficiently narrow based on QSAR model predictions Practical Utility of the Data How will the data be used? 

### This data would be needed in order to offer guidance on protective language from exposure to the NAA amide for freshwater estuarine fish should there be a need for such protective measures

. How could the data change the Agency’s decision or impact the Agen cy’s future decision

- making? 

### The data would be used in risk characterization and could change the conclusions of that assessment if toxicity is indicated to be at hazardous levels to these organisms.

### 40

Guideline Number: 850.1400 Study Title: Chronic Toxicity to Freshwater Fish using TGAI Napthaleneacetamide Rationale for Requiring the Data 

### For chronic toxicity to freshwater fish, toxicity data are being requested for the amide form of NAA, since no data have been submitted and the margin of safety b etween exposure and toxicity is sufficiently narrow based on QSAR model predictions. Practical Utility of the Data How will the data be used? 

### This data would be needed in order to offer guidance on protective language from chronic exposure to the NAA amide for freshwater fish should there be a need for such protective measures

. How could the data change the Agency’s decision or impact the Agency’s future decision

- making? 

### The data would be used in risk characterization and could change the conclusions of that assessment if chronic toxicity is indicated to be at hazardous levels to these organisms.

Guideline Number: 850.1300 Study Title: Chronic Toxicity to Freshwater Invertebrates using TGAI Napthaleneacetamide Rationale for Requiring the Data 

### For chronic toxicity to freshwater invertebrates, toxicity data are being requested for the amide form of NAA, since no data have been submitted and the margin of safety between exposure and toxicity is sufficiently narrow based on QSAR model predictions. Pr actical Utility of the Data How will the data be used? 

### This data would be needed in order to offer guidance on protective language from chronic exposure to the NAA amide for freshwater invertebrates should there be a need for such protective measures

. How could the data change the Agency’s decision or impact the Agency’s future decision

- making? 

### The data would be used in risk characterization and could change the conclusions of that assessment if chronic toxicity is indicated to be at hazardous levels to these organisms.



# 12. References

Cooke, TJ; Poli, DB; Sztein, AE; Cohen, JD. 2002. Evolutionary patterns in auxin action. Plant Molecular Biology. 49: 319

- 338. Crosby, D.G., Tang, C.S. 1969. Photodecomposition of 1

- Naphthaleneacetic Acid. 17(6), 1291

- 1293. European Commission Draft Assessment Report (DAR) (public version). Initial risk assessment provided by the rapporteur Member State France for the existing active substance 1

- Naphtylacetic Acid (1

- Naphthalene Acetic Acid). Volume 3, Annex 3, pa rt 5, B.8. Environmental fate and behaviour. August 2008. European Commission Draft Assessment Report (DAR) (public version). Initial risk assessment provided by the rapporteur Member State France for the existing active substance 1

- Naphtylacetic Acid (1

- Naphthalene Acetic Acid). Volume 3, Annex 3, part 6, B.9. Ecotoxicology. August 2008. Food and Agriculture Organization of the United Nations. 2000. FAO PESTICIDE DISPOSAL SERIES 8. Assessing Soil Contamination: A Reference Manual. Appendix 2. Paramete rs of pesticides that influence processes in the soil. Editorial Group, FAO Information Division: Rome, 2000. http://www.fao.org/DOCREP/003/X2570E/X2570E00.htm

### 41

USEPA. 2004. Overview of the Ecological Risk Assessment Process in the Office of Pesticide Programs . United States Environmental Protection Agency (USEPA). Environmental Fate and Effects Division. Office of Pesticide Programs. Available at http://www.epa.gov/espp/consultation/ecorisk

- overview.pdf

. USEPA. 2004. Revised EFED Risk Assessment for the Naphthaleneacetic Acid Reregistration Eligibility Decision: Revision Based on Application at Higher Use Rates (DP Ba rcode: D306433). Memorandum from A. Vaughan and J. Melendez (Environmental Fate and Effects Division) to Michael Goodis (Special Review and Reregistration Division) dated 10/27/2004. Office of Pesticide Programs. USEPA. 2009. Section 18 Request for Use of Naphthalenacetic Acid, Ethyl Ester (NAA EE) in California on Avocadoes to Control Sprout Growth (DP Barcode D361448). Memorandum from J. Melendez (Environmental Fate and Effects Division) to Andrew Ertm an et al. (Registration Division) dated 04/13/2009. Office of Pesticide Programs. USEPA. 2011. Section 3 Ecological Risk Assessment for the Proposed New Uses of Potassium Naphthalene Acetate and Sodium Naphthalene Acetate on Potato Seeds and/ or on Potato Foliage for the New Products RenewTM PGR and RenewTM C oncentrate PGR (DP Barcode D376108). Memorandum from J. Melendez (Environmental Fate and Effects Division) to Rosemary Kearns et al. (Registration Division) dated 05/20/2011. Office of Pesticide Programs. USEPA. 2011. Ecological Risk Assessment for the Pro posed Specific Section 18 Uses of the Product Rejuvenate Seed Treatment, Containing Potassium 1

- Naphthaleneacetic Acid on Potato Seeds

, and the Product Mitigate PGR, Containing Sodium 1

- Naphthalene acetic Acid on Potato Foliage in Idaho (DP Barcode D388693+ ). Memorandum from J. Melendez (Environmental Fate and Effects Division) to Keri Grinstead et al. (Registration Division) dated 05/20/2011. Office of Pesticide Programs. USEPA. 2012. Application for Registration of New Uses of 1

- naphthalene acetic acid (NA A), Sodium 1

- Naphthalene

- acetate, and Ethyl 1

- Naphthaleneacetate, on Rambutan, Avocado, Mamey Sapote and Mango , and Inclusion of the Pome Fruits Crop Group 11

- 10 (DP Barcode D402377). Memorandum from J. Melendez and A. Vaughan (Environmental Fate and Effe cts Division) to Rosemary Kearns et al. (Registration Division) dated 10/12/2014. Office of Pesticide Programs. USEPA

. 2014a. Screening Level Estimates of Agricultural Uses of NAA (Screening

- Level Usage Analysis or SLUA). Biological Economic Analysis Division. Office of Pesticide Programs. Report dated June 2, 2014. USEPA

. 2014b

. BEAD Chemical Profile (BCP) for Registration Review: Napthalene Acetates (NAA) (Case Number 0371) (1

- Naphthaleneacetamide (056001), 1

- Naphthaleneacetic acid (056002), Potassi um 1

- naphthaleneacetate (056003), Ammonium 1

- naphthaleneacetate (056004), Sodium 1

- naphthaleneacetate (056007), and Ethyl 1

- naphthaleneacetate (056008)). Memorandum from C arl Chen et al. ( Biological and Economic Analysis Division ) to Christina Scheltema (P esticide Reevaluation Division) dated August 3, 2014.

### 42



## Submitted Ecological Effects and Mammalian Toxicological Studies ( arranged by MRID number)

00042753 Fink, R.; Beavers, J.B.; Grimes, J.; et al. (1979) Final Report: Acute Oral LDI50

--

Bobwhite Quail: Project No. 113

- 154. (Unpublished study received Sep 19, 1979 under 264

- 336; prepared by Wildlife International, Ltd. and Washington College, submitted by Union Carbide Agricultural Products Co., Ambler, Pa.; CDL: 099029

- H)

00042754 Fink, R.; Be avers, J.B.; Grimes, J.; et al. (1979) Final Report: Acute Oral LDI50

-- M allard

Duck: Project No. 113

- 155. (Unpublished study received Sep 19, 1979 under 264

- 336; prepared by Wildlife International, Ltd. and Washington College, submitted by Union Carbide Ag ricultural Products Co., Ambler, Pa.; CDL: 099029

- I)

00042755 Union Carbide Corporation (1979) The Acute Toxicity of 72

- A112 to the Water

Flea,Daphniamagna

. Straus: UCES Project No. 11506

- 24

- 11. (Unpublished study received Sep 19, 1979 under 264

- 336; s ubmitted by Union Carbide Agricultural Products Co., Ambler, Pa.; CDL:099029

- J)

00042756 Morrissey, A.E. (1979) The Acute Toxicity o f 72

- A112 to the Rainbow Trout, Salmo

gairdneri Richardson: UCES Project No. 11506

- 24

- 10. (Unpublished study received S ep 19, 1979 under 264

- 336; submitted by Union Carbide Agricultural Products Co., Ambler, Pa.; CDL:099029

- K)

00042757 Schneider, C. (1979) The Acute Toxicity of 7 2

- A112 to the Bluegill Sunfish, Lepomis

macrochirus Rafinesque: UCES Project No. 11506

- 24

- 09 . (Unpublished study received Sep 19, 1979 under 264

- 336; submitted by Union Carbide Agricultural Products Co., Ambler, Pa.; CDL:099029

- L)

00042765 Miller, T.J.; McElroy, K. 1977. Teratology Study with NAA acid (Technical) by Gavage

in the Albino Rat. Huntingdon Research Center: HRC # R

- 4216

- 4 (1

- 350). Prepared by Pharmakon Laboratories, Unpublished Study. January 14, 1977.

00065840 Fink R; Beavers JB. 1979. Final Report: Acute Oral LD 50

-- Bobwhite Quail: Project

No. 113

- 153. (Unpublished stu dy received Sep 19, 1979 under 264

- 336 ; prepared by Wildlife Interna tional, Ltd. and Washington College, submitted by Union Carbide Agricultural Products Co., Inc., Ambler, Pa.; CDL:099029

- C)

00079520 Fink, R. (1976) Final Report: Eight

- day Dietary LCI5 0

-- Mallard Duck: Project No. 113

-

123. (Unpublished study received Sep 19, 1979 under 264

- 336; prepared by Truslow Farms, Inc., submitted by Union Carbide Agricultural Products Co., Inc., Ambler, Pa.; CDL:099029

- E)

00072749 Fink, R. (1976) Final Report: Ei ght

- Day Dietary LCI50

-- Bobwhite Quail: Project No.

113

- 118. (Unpublished study received Sep 19, 1979 under 264

- 336; prepared by Truslow Farms, Inc., submitted by Union Carbide Agricultural Products Co., Ambler, Pa.; CDL: 099029

- G)

00082526 LeBlanc, G.A.; Surprenant, D.C. (19 81) Acute Toxicity of Naphthal eneacetic Acid to the

Water Flea (Daphnia magna): Report #BW

- 81

- 4

- 866. (Unpublished study received Oct

### 43 14, 1981 under 264

- 336; prepared by EG & G, Bionomics, submitted by Union Car

- bide Agricultural Produc ts Co., Inc., Ambler, Pa.; CDL:246079

- A)

00082527 LeBlanc GA; Sousa JV. 1981a. Acute Toxicity of NAA to Bluegill (Lepomis

macrochirus): Report #BW

- 81

- 4

- 867. (Unpublished study received Oct 14, 1981 under 264

- 336; prepared by EG & G, Bionomics, submitt ed by Union Carbide Agricultural Products Co., Inc., Ambler, Pa.; CDL:246079

- B)

00082528 LeBlanc GA; Sousa JV. 1981b. Acute Toxicity of NAA to Rainbow Trout (Salmo

gairdneri): Report #BW

- 81

- 4

- 876. (Unpublished study received Oct 14, 1981 under 264

- 336; prepared by EG & G, Bionomics, submitted by Union Carbide Agricultural Products Co., Inc., Ambler, Pa.; CDL: 246079

- C)

00083052 Fink R. 1976. Final Report: Eight

- Day Dietary LC50

-- Mallard Duck: Project No.

113

- 119. (Unpublished study received Sep 1 9, 1979 under 264

- 336; prepared by Truslow Farms, Inc., submitted by Union Carbide Agricultural Products Co., Ambler, Pa.; CDL: 099029

- F)

00085909 Fink R. 1976. Final Report: Eight

- day Dietary LC50

-- Bobwhite Quail: Project No.

113

- 122. (Unpublished st udy received Sep 19, 1979 under 264

- 336; prepared by Truslow Farms, Inc., submitted by Union Carbide Agricultural Products Co., Inc., Ambler, Pa.; CDL:099029

- D)

00103128 Mallory, V.; Matthews, R.; Naismith, R.; et al. 1982. Acute Oral Toxicity Study in Rats

(14

- Day): Napthalene Acetic Acid: Study No. PH 402

- UC

- 001

- 82. Pharmakon Research International, Inc. April 29, 1982. Unpublished.

00108829 Myers, R.; Christopher, S.; Belliah, N.; et al. 1982. NAA (Naphthalene Acetic Acid)

Sodium Salt: Acute Toxic ity and Irritancy Studies: Project Report 45

- 45. May 27, 1982 Unpublished.

42470801 Terrell Y. 1992. Technical 1

- Naphthaleneacetic Acid, Ethyl Ester Acute Effects on the

Cladoceran, Daphnia magna: Lab Project Number: 92

- 330110

- 100

- 1: BR

- 1895A. Unpubl ished study prepared by Aqua Survey, Inc. 95 p.

42498101 Terrell Y. 1992. Technical 1

- Naphthaleneacetic Acid, Ethyl Ester: Acute Effects on the

Bluegill Sunfish, Lepomis macrochirus: Lab Project Number: 92

- 700110

- 100

- 1: BR

- 1895B. Unpublished study prep ared by Aqua Survey, Inc. 88 p.

42498101 Terrell Y. 1992. Technical 1

- Naphthaleneacetic Acid, Ethyl Ester: Acute Effects on the

Bluegill Sunfish, Lepomis macrochirus: Lab Project Number: 92

- 700110

- 100

- 1: BR

- 1895B. Unpublished study prepared by Aqua Sur vey, Inc. 88 p.

42564201 Harnish, W. (1992) Fruit Fix Super Concentrate 800 (NAA

- Ammonium 21. 4%) Tier I

Non

- target Plant Hazard Evaluation

- terrestrial Vegetative Vigor Study: Lab Project Number: 22925B002. Unpublished study prepared by Landis International, Inc. and AMVAC Chemical Corp. 87 p.

42564202 Harnish, W. (1992) K

- Salt Fruit Fix 800 (NAA

- Potassium Salt 24.2%) Tier I Non

- target

Plant Hazard Evaluation

- terrestrial Vegetative Vigor Study: Lab Project Number:

### 44 22925B004. Unpublished study p repared by Landis International, Inc. and AMVAC Chemical Corp. 92 p.

42582201 Hughes, J.; Alexander, M. (1992) The Toxicity of K

- Salt Fruit Fix 800 to Selenastrum

capricornutum: Lab Project Number: B015

- 001

- 1. Unpublished study prepared by Malcolm Pirnie, Inc. 37 p.

42582202 Hughes J; Alexander M. 1992b. The toxicity of K

- Salt Fruit Fix 800 to Lemna gibba G3:

Lab Project Number: B015

- 001

- 2. Unpublished study prepared by Malcolm Pirnie, Inc. 36 p.

42584202 Campbell S; Jaber M. 1992. Technical 1

- Naphthalene Acetic Acid Ethyl Ester: A Dietary

LC50 Study with the Northern Bobwhite: Lab Project Number: 246

- 109R. Unpublished study prepared by Wildlife International Ltd. 37 p.

42584203 Harnish W. 1992. K

- Salt Fruit Fix 800 (NAA

- Potassuim 24. 2 %): Tier I and Tier II

Non

- Target Plant Hazard Evaluation: Terrestrial Seed Germination and Seedling Emergence Study: Lab Project Number: 22925B003. Unpublished study prepared by Landis International, Inc. 406 p. (NAA

- Potassuim 24. 2%): Tier I and Tier II Non

- Target Plant Hazard Evaluation: Terrestrial Seed Germination and Seedling Emergence Study: Lab Project Number: 22925B003. Unpublished study prepared by Landis International, Inc. 406 p.

42582204 Hughes, J.; Alexander, M. (1992) The Toxicity of Fruit Fix Super Concentrate 800

toLemna gibba G3: Lab Project Number: B015

- 001

- 4. Unpublished study prepared by Malcolm Pirnie, Inc. 35 p. (NAA Ammonium salt)

42589901 Harnish W. 1992. Fruit Fix Super Concentrate 800: Tier I and II Non

- target Plant Hazard

Evaluation

-- Terrestrial Seed Germination and Seedling Emergence Study: Lab Project Number: 22925B001. Unpublished study prepared by Landis Int'l, Inc. 502 p.

43141101 Harnish W. 1994. K

- Salt Fruit Fix 800 Tier II Non

- Target Plant Hazard

Evalua tion

- Terrestrial Vegetative Vigor: Final Report: Lab Project Number: 22925B006: 1231

- 93

- 229

- 02

- 25B

- 02. Unpublished study prepared by Landis International, Inc. 52 p.

43168101 Harnish, W. (1994) Fruit Fix Super Concentrate 800 (NAA

- Ammonium 21.4%): Tier I

Non

- Target Plant Hazard Evaluation

- Terrestrial Vegetative Vigor Study on Carrot: Supplement: Lab Project Number: 22925B002: 21

- 92

- 229

- 01

- 25B

- 02. Unpublished study prepared by Landis International, Inc. 52 p.

43482101 Obrist, J. (1994) NAA Bridging Stu dy: Determination of the Half

- life of

Naphthaleneacetic Acid, (NAA), Naphthaleneacetamide, and Naphthaleneacetic Acid Ethyl Ester on Apple Leaves: Lab Project Number: 94399. Unpublished study prepared by Pan

- Agricultural Labs, Inc. 136 p. MRID 43482101.

43494101 Kuhn, J. 1994. Acute Oral Toxicity Study in Rats: Technical 1

- Naphthaleneacetic Acid,

Ethyl Ester: Final Report: Lab Project Number: 1351

- 94. Unpublished study prepared by Stillmeadow, Inc. 21 p.

### 45

43495901 Kuhn, J. 1994. Acute Oral Toxici ty Study in Rats: Technical 1

- Napthaleneacetamide:

Final Report: Lab Project Number: 1346

- 94: S9

- FF81

- 1. Unpublished study prepared by Stillmeadow, Inc. 13 p.

43744201 Kangas, L. 1995. A 52

- Week Oral (Capsule) Toxicity Study of 1

- Naphthaleneacetic Ac id

Sodium Salt in the Beagle Dog: Lab Project Number: 85212. Unpublished study prepared by Bio

- Research Labs, Ltd. 517 p.

43803201 Harnish W. 1995a. NAA: Determination of the Effects of NAA Ammonium Salt. (800

g/Gallon End Use Formulation) on Seed Germination and Seedling Emergence: Final Report: Lab Project Number: 22925B007: 1231

- 94

- 229

- 01

- 25B

- 01. Unpublished study prepared by Landis International, Inc. 107 p.

44157501 Drummond, J. 1992. Two

- Year Chronic Toxicity/Oncogenicity Study in Rats with

1

- Naphthaleneacetic Acid Sodium salt (1

- Na

- NAA) (MRD

- 92

- 349): Final Report: Lab Project Number: 134970B. Unpublished study prepared by Exxon Biomedical Sciences, Inc. 2823 p.



## Naphthalene Acetic Acid Environmental Fate Bibliography ( a rranged b y guideline number )

161

- 1 Hydrolysis

MRID Citation Reference

129382 Feung, C.; Carswell, G.; Heintzelman, R. (1983) Naphthaleneacetic Acid: Hydrolysis of

Ethyl Naphthaleneacetate and Naphthalene

- acetamide: Project No. 860R10. (Unpublished study received Jun 14, 1983 under 264

- 29; submitted by Union Carbide Agricultural Pro ducts Co., Inc., Research Triangle Park, NC; CDL: 250640

- A)



### 161

- 4 Photodegradation

- air

MRID Citation Reference

4943 Crosby, D.G.; Bowers, J.B.; Shindy, W.W. (1970) 1

- Naphthaleneacetic acid in Olives.

Includes two undated methods. (Unpublished study received Nov 25, 1970 under 1E1099; prepared by Univ. of California

-- Davis, Dept. of Environmental Toxicology and Agricultu ral Experiment Station, submitted by Interregional Research Project No. 4, New Brunswick, N.J.; CDL:090859

- B)



### 162

- 1 Aerobic soil metabolism

MRID Citation Reference

### 46

4943 Crosby, D.G.; Bowers, J.B.; Shindy, W.W. (1970) 1

- Naphthaleneacetic acid in Olives.

Includes two undated methods. (Unpublished study received Nov 25, 1970 under 1E1099; prepared by Univ. of California

- Davis, Dept. of Environmental Toxicology and Agricultur al Experiment Station, submitted by Interregional Research Project No. 4, New Brunswick, N.J.; CDL:090859

- B)



### 163

- 1 Leach ing /adsorp tion /desorption

MRID Citation Reference

115359 Anderson, W.; Linder, P.; Mitchell, J. (1952) Evaporation of some plant growth regulators

and its possible effect on their activity. Science 116 (Nov 7):502

- 503. (Also In unpublished submission received Jun 14, 1971 under 748

- 207; submitted by PPG Industries, Inc., Barberton, OH; CDL:009051

- C)



### Non

- Guideline

- summaries

162239 Amvac Chemical Corp. 1986. [Product Chemistry of 1

- Naphthalene Acetic Acid]. Unpublished compilation. 23 p.

40522903 Feiler W. 1987. NAA: Physical and Chemical Characteristics. Unpublished study prepared by Amvac Chemical Corp. 3 p.



### 2014 Waiver Requests on Multiple Guideline Requirements

MRID Citation Reference

49298203 SciReg, Inc. (2014) 1

- Naphthaleneacetic Acid Technical, Soldium Salt: Toxicology,

Terrestrial and Aquatic Nontarget Organism, Environmental Fate, Post

- Application Exp osure, and Residue Chemistry Waiver Requests. Unpublished study. 28p

. 49298303 SciReg, Inc. (2014) 1

- Naphthaleneacetic Acid Technical, Potassium Salt: Toxicology,

Terrestrial and Aquatic Nontarget Organism, Environmental Fate, Post

- Application Exposure, and Residue Chemistry Waiver Requests. Unpublished study prepared by SciReg, Inc. 28p.



### Non

- Guideline Studies

MRID Citation Reference

43482101 Obrist, J. (1994) NAA Bridging Study: Determination of the Half

- life of Naphthaleneacetic

Acid, (NAA), Naphthaleneacetamide, and Naphthaleneacetic Acid Ethyl Ester on Apple Leaves: Lab Project Number: 94399. Unpublished study prepared by Pan

- Agricultural L abs, Inc. 136 p.

### 47

47478605 Hambrick, A. (1995) 1

- Naphthaleneacetamide

- Ultraviolet

- Visible Absorption Spectra.

Project Number: 4506/95/0247/AS/001, 4506/95/0247/AS/000, 19/C121. Unpublished study prepared by Ricerca, Inc. 39 p.

48742401 Woolley, A.; Atwal, S. (2012) Amcotone: Determination of Long

- term Storage Stability and

Physico

- chemical Characteristics. Project Number: 2862/0002R. Unpublished study prepared by Harlan Laboratories, Ltd. 65p.

05011538 Clifford, D.R.; Woodcock, D. (1968) Fungal deto xication

-- IX_ Metabolism of 1

-

naphthaleneacetic acid by Aspergillus niger Van Tiegh. Phytochemistry 7(9):1499

- 1502

05008826 Doi, S.; Takahashi, T.; Yanagishima, N. (1973) Auxin

- induced large cell mutants in

Saccharomyces cerevisiae I Induction, and bioch emical and genetic characters. Japanese Journal of Genetics. A translation of: Idengaku Zasshi. 48(3):185

- 195.

05010797 Ukita, T.; Tamemasa, O.; Motomatsu, H. (1951) Antibacterial action of fatty acids_ VIII_

Syntheses of fatty acids with naphthyl, naphth omethyl and benzyl groups in alpha

- position and their antibacterial action. Yakugaku Zasshi. ?Journal of Pharmaceutical Society of Japan.| 71(4):289

- 297

05009027 Gramlich, J.V.; Frans, R.E. (1964) Kinetics of~Chlorella~inhibition by herbicides. Weeds

12(3):184

- 189.

05010966 Klein, D.T. (1962) Effect of growth

- regulators on mutants of~Neurospora crassa.

Physiologia Plantarum 15:239

- 245.

05005277 Loveless, L.E.; Spoerl, E.; Weisman, T.H. (1954) A survey of effects of chemicals on

division and growth of yeast and Escherichia coli. Journal of Bacteriology 68:637

- 644.

05012526 Croxall, H.E.; Ogilvie, L. (1940) The effect of seed dressings containing growth

- promoting

substances on lettuce, tomato, sugar beet and dwarf bean. Pages 29

- 34,~In~Long Ashton Research Station, University of Bristol, Report 1940. Bristol, England: Long Ashton Agricultural and Horticultural Research Station.

### 48



## Appendix A. Naphthalene A cetic Acid & its Related Active Ingredients

Name, abbreviation and CAS Number Structure 1

- Naphthalene acetic acid (NAA) CAS No. 86

- 87

- 3 SMILES Code: O=C(O)Cc(c(c(ccc1)cc2)c1)c2



### Sodium 1

- naphthalene acetate (Na

- NAA) CAS No. 61

- 31

- 4

Potassium 1

- naphthalene acetate (K

- NAA) CAS No. 15165

- 79

- 4

Ammonium 1

- naphthalene acetate (NH 4 

### - NAA) CAS No. 25545

- 89

- 5

1

- naphthalene acetic acid ethyl ester (NAA EE) CAS No. 2122

- 70

- 5

1

- naphthalene acetamide (NAAm) CAS No. 86

- 86

- 2

### 49



## Appendix B. Output Files from CATABOL v.4.55 and Potential Metabolites of Naphthalene acetic acid

Note: This output file was previously reported in the EFED Reregistration Eligibility Decision science chapter.

Table B 1. Output file from CATABOL v.4.55

Trans Level Quantity P_obtain P_stable Log K OW Smiles
1 391 1 0.999 1 0.999 2.6044 c1(CC(=O)O)c2c(cccc2)ccc1
2 363 2 0.000776 0.001 0.000776 3.7163 c1(C)c2c(cccc2)ccc1
3 78 3 0 0.000224 0 2.2515 c1(CO)c2c(cccc2)ccc1
4 54 4 0 0.000224 0 2.8862 c12c(c(C=O)ccc1)cccc2
5 272 5 0.000031 0.000224 0.000031 3.0504 C(=O)(O)c1c2c(cccc2)ccc1
6 120 6 0 0.000193 0 2.2086 c1(O)c(O)c2c(cccc2)cc1
7 105 7 0 0.000193 0 1.0405 C(=O)(O)C(=O)C=Cc1c(O)cccc1
8 54 8 0 0.000193 0 2.007 c1(O)c(C=O)cccc1
9 205 9 0.000018 0.000193 0.000018 2.2447 C(=O)(O)c1c(O)cccc1
10 129 10 0 0.000175 0 1.0326 c1(O)c(O)cccc1
11 49 11 0 0.000175 0

- 0.4424 C(=O)(O)C(O)=CC=CC=O
12 54 12 0 0.000175 0 0.35 C=O
13 7 13 0 0.000175 0

- 0.4605 C(=O)O
14 60 12 0 0.000175 0 0.6346 C(=O)(O)C(O)=CC=C
15 46 13 0 0.000175 0

- 0.3974 C(=O)(O)C(=O)CC=C
16 101 14 0 0.000175 0

- 1.7993 C(=O)(O)C(=O)CC(C)O
17 54 15 0 0.000175 0

- 0.1659 C(C)=O
18 10 16 0 0.000175 0 0.0868 C(C)(=O)O
19 13 15 0 0.000193 0

- 1.2432 C(=O)(O)C(C)=O



### The Smiles codes were converted into structures and the names of such structures were located. These appear in Table B2

.

### 50

Table B 2. Naphthalene acetic acid and its Potential Metabolites 10 

### 1

- Napthalene acetic acid

1

- methyl

- naphthalene (also a photodegradate)

2

- naphthylmethanol (also a photodegradate)

2

- naphthaldehyde (also a photodegradate)

10 Structures were drawn with PubChem at: http://pubchem.ncbi.nlm.nih.gov/edit2/index.html?cnt=0

.

### 51

2

- naphthoic acid (also a photodegradate)

naphthalene

- 1,2

- diol

(3E)

- 4

- (2

- hydroxyphenyl)

- 2

- oxobut

- 3

- enoic acid

salicylaldehyde

### 52

salicylic acid

Pyrocatechol

(2Z,4E)

- 2

- hydroxy

- 6

- oxohexa

- 2,4

- dienoic acid

(2Z)

- 2

- hydroxypenta

- 2,4

- dienoic acid

2

- oxopent

- 4

- enoic acid

### 53

4

- hydroxy

- 2

- oxopentanoic acid

2

- oxopropanoic acid

acetaldehyde

acetic acid

formaldehyde

formic acid

### 54



## Appendix C. Output File from EPISUITE

CAS Number: 000086

- 87

- 3 SMILES : O=C(O)Cc(c(c(ccc1)cc2)c1)c2 CHEM : NAPHTHALENEACETIC ACID MOL FOR: C12 H10 O2 MOL WT : 186.21

------------------------------ EPI SUMMARY (v4.10)

-------------------------- Physical Property Inputs: Log Kow (octanol

- water): 2.24 Boiling Point (deg C) :

------ Melting Point (deg C) : 135.00 Vapor Pressure (mm Hg) :

------ Water Solubility (mg/L): 420 Henry LC (atm

- m3/mole) :

------

KOWWIN Program (v1.68) Results:

===============================

Log Kow(version 1.68 estimate): 2.60

Experimental Database Structure Match:
Name : NAPHTH ALENEACETIC ACID CAS Num : 000086

- 87

- 3 Exp Log P: 2.24 Exp Ref : SANGSTER (1993)

SMILES : O=C(O)Cc(c(c(ccc1)cc2)c1)c2 CHEM : NAPHTHALENEACETIC ACID MOL FOR: C12 H10 O2 MOL WT : 186.21

------- +

----- +

-------------------------------------------- +

--------- +

-------- TYPE | NUM | LOGKOW FRAGMENT DESCRIPTION | COEFF | VALUE

------- +

----- +

-------------------------------------------- +

--------- +

-------- Frag | 1 |

- CH2

- [aliphatic carbon] | 0.4911 | 0.4911 Frag | 10 | Aromatic Carbon | 0.2940 | 2.9400 Frag | 1 |

- COOH [acid, aliphatic attach] |

- 0.6895 |

- 0.6895 Factor| 1 | Aromatic

- C[

- C or

- H]

- COOH correction |

- 0.3662 |

- 0.3662 Const | | Equation Constant | | 0.2290

------- +

----- +

-------------------------------------------- +

--------- +

-------- Log Kow = 2.6044

MPBPVP (v1.43) Program Results:

=============================== Experimental Database Structure Match: Name : NAPHTHALENEACETIC ACID CAS Num : 000086

- 87

- 3 Exp MP (deg C): 135 Exp BP (deg C):

--- Exp VP (mm Hg):

---

SMILES : O=C(O)Cc(c(c(ccc1)cc2)c1)c2 CHEM : NAPHTHALENEACETIC ACID MOL FOR: C12 H10 O2 MOL WT : 186.21

------------------------ SUMMARY MPBVP v1.43

--------------------

Boiling Point: 351.44 deg C (Adapted Stein and Brown Method)

Melting Point: 184.08 deg C (Adapted Joback Method)

### 55

Melting Point: 91.54 deg C (Gold and Ogle Method) Mean Melt Pt : 137.81 deg C (Joback; Gold,Ogle Methods) Selected MP: 114.68 deg C (Weighted Value)

Vapor Pressure Estimations (25 deg C): (Using BP: 351.44 d eg C (estimated)) (Using MP: 135.00 deg C (user entered)) VP: 4.38E

- 006 mm Hg (Antoine Method) : 0.000584 Pa (Antoine Method) VP: 9.57E

- 006 mm Hg (Modified Grain Method) : 0.00128 Pa (Modified Grain Method) VP: 1.97E

- 005 mm Hg (Mackay Method) : 0.00263 Pa (Mackay Method) Selected VP: 9.57E

- 006 mm Hg (Modified Grain Method)

: 0.00128 Pa (Modified Grain Method) Subcooled liquid VP: 0.000122 mm Hg (25 deg C, Mod

- Grain method)

: 0.0163 Pa (25 deg C, Mod

- Grain method)

------- +

----- +

-------------------- +

---------- +

--------- TYPE | NUM | BOIL DESCRIPTION | COEFF | VALUE

------- +

----- +

-------------------- +

---------- +

--------- Group | 1 |

- CH2

- | 24.22 | 24.22 Group | 1 |

- COOH (acid) | 169.83 | 169.83 Group | 7 | CH (aromatic) | 28.53 | 199.71 Group | 1 |

- C (aromatic) | 30.76 | 30.76 Group | 2 | C (3a aromatic) | 45.46 | 90.92 * | | Equation Constant | | 198.18

=============+====================+==========+========= RESULT

- uncorr| BOILING POINT in deg Kelvin | 713.62 RESULT

- corr | BOILING POINT in deg Kelvin | 624.60

| BOILING POINT in deg C | 351.44

-------------------------------------------------------

------- +

----- +

-------------------- +

---------- +

--------- TYPE | NUM | MELT DESCRIPTION | COEFF | VALUE

------- +

----- +

-------------------- +

---------- +

- -------- Group | 1 |

- CH2

- | 11.27 | 11.27 Group | 1 |

- COOH (acid) | 155.50 | 155.50 Group | 7 | CH (aromatic) | 8.13 | 56.91 Group | 1 |

- C (aromatic) | 37.02 | 37.02 Group | 2 | C (3a aroma tic) | 37.02 | 74.04 * | | Equation Constant | | 122.50

=============+====================+==========+========= RESULT | MELTING POINT in deg Kelvin | 457.24

| MELTING POINT in deg C | 184.08

------- ------------------------------------------------

Water Sol from Kow (WSKOW v1.42) Results:

========================================

Water Sol: 734.3 mg/L

Experimental Water Solubility Database Match: Name : NAPHTHALENEACETIC ACID CAS Num : 000086

- 87

- 3 Exp WSol : 420 mg/L (20 deg C) Exp Ref : YALKOWSKY,SH & DANNENFELSER,RM (1992)

SMILES : O=C(O)Cc(c(c(ccc1)cc2)c1)c2 CHEM : NAPHTHALENEACETIC ACID MOL FOR: C12 H10 O2 MOL WT : 186.21

### 56

---------------------------------- WSKOW v1.42 Results

------------------------ Log Kow (estimated) : 2.60 Log Kow (experimental): 2.24 Cas No: 000086

- 87

- 3 Name : NAPHTHALENEACETIC ACID Refer : SANGSTER (1993) Log Kow used by Water solubility estimates: 2.24 (user enter ed)

Equation Used to Make Water Sol estimate: Log S (mol/L) = 0.693

- 0.96 log Kow

- 0.0092(Tm

- 25)

- 0.00314 MW + Correction

Melting Pt (Tm) = 135.00 deg C (Use Tm = 25 for all liquids)

Correction(s): Value

-------------------- ----- Acid, aliphatic 0.650

Log Water Solubility (in moles/L) :

- 2.404 Water Solubility at 25 deg C (mg/L): 734.3

WATERNT Program (v1.01) Results:

===============================
Water Sol (v1.01 est): 155.62 mg/L

Experimental Water Solubility Database Match: Name : NAPHTHALENEACETIC ACID CAS Num : 000086

- 87

- 3 Exp WSol : 420 mg/L (20 deg C) Exp Ref : YALKOWSKY,SH & DANNENFELSER,RM (1992)

SMILES : O=C(O)Cc(c (c(ccc1)cc2)c1)c2 CHEM : NAPHTHALENEACETIC ACID MOL FOR: C12 H10 O2 MOL WT : 186.21

------- +

----- +

-------------------------------------------- +

---------- +

--------- TYPE | NUM | WATER SOLUBILITY FRAGMENT DESCRIPTION | COEFF | VALUE

------- +

- ---- +

-------------------------------------------- +

---------- +

--------- Frag | 1 |

- CH2

- [aliphatic carbon] |

- 0.5370 |

- 0.5370 Frag | 7 | Aromatic Carbon (C

- H type) |

- 0.3359 |

- 2.3510 Frag | 1 |

- COOH [acid, aliphatic attach] | 1.1808 | 1.1808 Frag | 3 | Aromatic Carbon (C

- substituent type) |

- 0.5400 |

- 1.6199 Const | | Equation Constant | | 0.2492

------- +

----- +

----- --------------------------------------- +

---------- +

--------- Log Water Sol (moles/L) at 25 dec C =

- 3.0779 Water Solubility (mg/L) at 25 dec C = 155.62

ECOSAR Program (v1.00) Results:

============================== SMILES : O=C(O)Cc(c(c(ccc1)cc2)c1)c2 CHEM : NAPHTHALENEACETIC ACID CAS Num: ChemID1: ChemID2: ChemID3: MOL FOR: C12 H10 O2 MOL WT : 186.21 Log Kow: 2.60 (KowWin estimate) Melt Pt: 135.00 deg C Wat Sol: 420 mg/L (meas ured)

### 57

ECOSAR v1.00 Class(es) Found

------------------------------ Neutral Organics

- acid Predicted ECOSAR Class Organism Duration End Pt mg/L (ppm)

=========================== ================== ======== ====== ==========

-- > Acid moeity found: Predicted values multiplied by 10

Neutral Organics

- acid : Fish 96

- hr LC50 421.790 * Neutral Organics

- acid : Fish 14

- day LC50 430.653 * Neutral Organics

- acid : Daphnid 48

- hr LC50 260.075 Neutral Organics

- acid : Green Algae 96

- hr EC50 160.505 Neutral Organics

- acid : Fish 30

- day ChV 45.760 Neutral Organics

- acid : Daphnid ChV 33.180 Neutral Organics

- acid : Green Algae ChV 67.834 Neutral Organics

- acid : Fish (SW) 96

- hr LC50 560.081 * Neutral Organics

- acid : Mysid Shrimp 96

- hr LC50 273.308 Neutral Organics

- acid : Fish (SW) ChV 86.947 Neutral Organics

- acid : Mysid Shrimp (SW) ChV 19.750 Neutral Organics

- acid : Eart hworm 14

- day LC50 2802.408 *

Note: * = asterisk designates: Chemical may not be soluble

enough to measure this predicted effect.

Neutral Organics:

---------------- For Fish LC50 (96

- h), Daphnid LC50, Mysid: If the log Kow i s greater than 5.0, or if the compound is solid and the LC50 exceeds the water solubility by 10X, no effects at saturation are predicted.

For Fish LC50 (14

- day) and Earthworm LC50: If the log Kow is greater than 6.0, or if the compound is solid and the LC50 exceeds the water solubility by 10X, no effects at saturation are predicted.

For Green Algae Acute Toxicity Values: If the log Kow of the chemical is greater than 6.4, or if the compound is solid and the EC50 exceeds the water solubility by 10X, no effects at saturation are predicted for these endpoints.

For All Chronic Toxicity Values: If the log Kow of the chemical is greater than 8.0, or if the compound is solid and the ChV exceeds the water solubility by 10X, no effects at saturation are p redicted for these endpoints.

ECOSAR v1.00 SAR Limitations:

---------------------------- Maximum LogKow: 5.0 (Fish 96

- hr LC50; Daphnid LC50, Mysid LC50) Maximum LogKow: 6.0 (Fish 14

- day LC50; Earthworm LC50) Maximum LogKow: 6.4 (Green Algae EC50) Maximum LogKow: 8.0 (ChV) Maximum Mol Wt: 1000

HENRYWIN (v3.20) Program Results:

=============================

Bond Est : 4.32E

- 009 atm

- m3/mole (4.37E

- 004 Pa

- m3/mole) Group Est: Incomplete

SMILES : O=C(O)Cc(c(c(ccc1)cc2)c1)c2 CHEM : NAPHTHALENEACETIC ACID MOL FOR: C12 H10 O2

### 58

MOL WT : 186.21

--------------------------- HENRYWIN v3.20 Results

--------------------------

---------- +

--------------------------------------------- +

--------- +

---------- CLASS | BOND CONTRIBUTION DE SCRIPTION | COMMENT | VALUE

---------- +

--------------------------------------------- +

--------- +

---------- HYDROGEN | 2 Hydrogen to Carbon (aliphatic) Bonds | |

- 0.2394 HYDROGEN | 7 Hydrogen to Carbon (aromatic) Bonds | |

- 1.0801 HYDROGEN | 1 Hydrogen to Oxygen Bonds | | 3.2318 FRAGMENT | 1 C

- Car | | 0.1619 FRAGMENT | 1 C

- CO | | 1.7057 FRAGMENT | 1 1 Car

- Car | | 2.9019 FRAGMENT | 1 CO

- O | | 0.0714

---------- +

--------------------------------------------- +

--------- +

---------- RESULT | BOND ESTIMATION METHOD f or LWAPC VALUE | TOTAL | 6.753

---------- +

--------------------------------------------- +

--------- +

---------- HENRYs LAW CONSTANT at 25 deg C = 4.32E

- 009 atm

- m3/mole = 1.76E

- 007 unitless = 4.37E

- 004 Pa

- m3/mole

-------- +

----------------------------------------------- +

------------ +

--------

| GROUP CONTRIBUTION DESCRIPTION | COMMENT | VALUE

-------- +

----------------------------------------------- +

------------ +

--- -----

| 7 Car

- H (Car)(Car) | | 0.77 | 1 Car (C)(Car)(Car) | | 0.70 | 2 Car (Car)(Car)(Car) fused | | 0.94 | 1 CO (C)(O) | | 4.09 | 1 O

- H (CO) | | 1.45 | MISSING Value for: CH2 (Car)(CO)

-------- +

------------------------------------ ----------- +

------------ +

-------- RESULT | GROUP ESTIMATION METHOD for LOG GAMMA VALUE | INCOMPLETE | 7.95

-------- +

----------------------------------------------- +

------------ +

--------

For Henry LC Comparison Purposes: Exper Database: none avai lable
User

- Entered Henry LC: not entered Henrys LC [via VP/WSol estimate using User

- Entered or Estimated values]: HLC: 5.583E

- 009 atm

- m3/mole (5.657E

- 004 Pa

- m3/mole) VP: 9.57E

- 006 mm Hg (source: MPBPVP) WS: 420 mg/L (source: User

- Entered)

Log Octanol

- Air (KOAWIN v1.10) Results:

======================================

Log Koa: 8.993

SMILES : O=C(O)Cc(c(c(ccc1)cc2)c1)c2 CHEM : NAPHTHALENEACETIC ACID MOL FOR: C12 H10 O2 MOL WT : 186.21

--------------------------- KOAWIN v1.10 Results

--------------------------
Log Koa (octanol/air) estimate: 8.993 Koa (octanol/air) estimate: 9.839e+008 Using: Log Kow: 2.24 (user entered) HenryLC: 4.32e

- 009 atm

- m3/mole (HenryWin est) Log Kaw:

- 6.753 (air/water part.coef.)

LogKow : 2.24 (exp database) LogKow : 2.60 (KowWin estimate) Henry LC:

--- atm

- m3/mole(exp database)

### 59

Henry LC: 4.32e

- 009 atm

- m3/mole (HenryWin bond estimate)

Log Koa (octanol/air) estimate: 9.353 (fro m KowWin/HenryWin)

BIOWIN (v4.10) Program Results:

============================== SMILES : O=C(O)Cc(c(c(ccc1)cc2)c1)c2 CHEM : NAPHTHALENEACETIC ACID MOL FOR: C12 H10 O2 MOL WT : 186.21

--------------------------- BIOWIN v4.10 Results

------------- ---------------

Biowin1 (Linear Model Prediction) : Biodegrades Fast Biowin2 (Non

- Linear Model Prediction): Biodegrades Fast Biowin3 (Ultimate Biodegradation Timeframe): Weeks Biowin4 (Primary Biodegradation Timeframe): Days Biowin5 (MITI Linear Model Prediction) : Does Not Biodegrade Fast Biowin6 (MITI Non

- Linear Model Prediction): Does Not Biodegrade Fast Biowin7 (Anaerobic Model Prediction): Does Not Biodegrade Fast Ready Biodegradability Prediction: NO

------ +

----- +

-------------------------------------------- +

--------- +

--------- TYPE | NUM | Biowin1 FRAGMENT DESCRIPTION | COEFF | VALUE

------ +

----- +

-------------------------------------------- +

--------- +

--------- Frag | 1 | Alipha tic acid [

- C(=O)

- OH] | 0.0727 | 0.0727 Frag | 1 | Alkyl substituent on aromatic ring | 0.0547 | 0.0547 MolWt| * | Molecular Weight Parameter | |

- 0.0887 Const| * | Equation Constant | | 0.7475

============+============================================+=========+========= RESULT | Biowin1 (Linear Biodeg Probability) | | 0.7863

============+============================================+=========+== =======

------ +

----- +

-------------------------------------------- +

--------- +

--------- TYPE | NUM | Biowin2 FRAGMENT DESCRIPTION | COEFF | VALUE

------ +

----- +

-------------------------------------------- +

--------- +

--------- Frag | 1 | Aliphatic acid [

- C(=O)

- OH] | 0.6431 | 0.6431 Frag | 1 | Alkyl substituent on aromatic ring | 0.5771 | 0.5771 MolWt| * | Molecular Weight Parameter | |

- 2.6442

============+======================== ====================+=========+========= RESULT | Biowin2 (Non

- Linear Biodeg Probability) | | 0.8299

============+============================================+=========+=========

A Probability Greater Than or Equal to 0.5 indicates

-- > Biodegrades Fast A Probability Less Than 0.5 indicates

-- > Does NOT Biodegrade Fast

------ +

----- +

-------------------------------------------- +

--------- +

--------- TYPE | NUM | Biowin3 FRAGMENT DESCRIPTION | COEFF | VALUE

------ +

----- +

-------------------------------------------- +

--------- +

--------- Frag | 1 | Aliphatic acid [

- C(=O)

- OH] | 0.3646 | 0.3646 Frag | 1 | Alkyl substituent on aromatic ring |

- 0.0749 |

- 0.0749 MolWt| * | Molecular Weight Parameter | |

- 0.4115 Const| * | Equation Constant | | 3.1992

============+============================================+=========+========= RESULT | Biowin3 (Survey Model

- Ultimate Biodeg) | | 3.0774

============+============================================+=========+=========

------ +

----- +

-------------------------------------------- +

--------- +

--------- TYPE | NUM | Biowin4 FRAGMENT DESCRIPTION | COEFF | VALUE

------ +

----- +

-------------------------------------------- +

--------- +

--------- Frag | 1 | Aliphatic acid [

- C(=O)

- OH] | 0.3856 | 0.3856 Frag | 1 | Alkyl substituent on aromatic ring |

- 0.0685 |

- 0.0685 MolWt| * | Molecular Weight Parameter | |

- 0.2687

### 60

Const| * | Equation Constant | | 3.8477

============+============================================+=========+========= RESULT | Biowin4 (Survey Model

- Primary Biodeg) | | 3.8961

============+============================================+=========+=========

Result Classification: 5.00

- > hours 4.00

- > days 3.00

- > weeks (Primary & Ultimate) 2.00

- > months 1.00

- > longer

--- --- +

----- +

-------------------------------------------- +

--------- +

--------- TYPE | NUM | Biowin5 FRAGMENT DESCRIPTION | COEFF | VALUE

------ +

----- +

-------------------------------------------- +

--------- +

--------- Frag | 1 | Aliphatic acid [

- C(=O)

- OH] | 0.1812 | 0.1812 Frag | 1 | Aromatic

- CH2 |

- 0.0557 |

- 0.0557 Frag | 7 | Aromatic

- H | 0.0082 | 0.0575 MolWt| * | Molecular Weight Parameter | |

- 0.5540 Const| * | Equation Constant | | 0.7121

============+============================================+=========+========= RESULT | Biowin5 (MITI Linear Biodeg Probab ility) | | 0.3412

============+============================================+=========+=========

------ +

----- +

-------------------------------------------- +

--------- +

--------- TYPE | NUM | Biowin6 FRAGMENT DESCRIPTION | COEFF | VALUE

------ +

----- +

-------------------------------------------- +

--------- +

--------- Frag | 1 | Aliphatic acid [

- C(=O)

- OH] | 1.1346 | 1.1346 Frag | 1 | Aromatic

- CH2 |

- 0.1246 |

- 0.1246 Frag | 7 | A romatic

- H | 0.1201 | 0.8410 MolWt| * | Molecular Weight Parameter | |

- 5.3757

============+============================================+=========+========= RESULT |Biowin6 (MITI Non

- Linear Bi odeg Probability)| | 0.2691

============+============================================+=========+=========

A Probability Greater Than or Equal to 0.5 indicates

-- > Readily Degradable A Probability Less Than 0.5 indicates

-- > NOT Readily Degrada ble

------ +

----- +

-------------------------------------------- +

--------- +

--------- TYPE | NUM | Biowin7 FRAGMENT DESCRIPTION | COEFF | VALUE

------ +

----- +

-------------------------------------------- +

--------- +

--------- Frag | 1 | Aliphatic acid [

- C(=O)

- OH] | 0.1868 | 0.1868 Frag | 1 | Alkyl substituent on aromatic ring |

- 0.1145 |

- 0.1145 Frag | 1 | Aromatic

- CH2 |

- 0.0073 |

- 0.0073 Frag | 7 | Aromatic

- H |

- 0.0954 |

- 0.6680 Const| * | Equation Constant | | 0.8361

============+============================================+=========+========= RESULT | Biowin7 (Anaerobic Linear Biodeg Prob) | | 0.2331

============+============================================+=========+=========

A Probability Greater Than or Equal to 0.5 indicates

-- > Biodegrades Fast A Probability Less Than 0.5 indicates

-- > Does NOT Biodegrade Fast

Rea dy Biodegradability Prediction: (YES or NO)

---------------------------------------------- Criteria for the YES or NO prediction: If the Biowin3 (ultimate survey model) result is "weeks" or faster (i.e. "days", "days to weeks", or "weeks" AND the Biowi n5 (MITI linear model) probability is >= 0.5, then the prediction is YES (readily biodegradable). If this condition is not satisfied, the prediction is NO (not readily biodegradable). This method is based on application of Bayesian analysis to ready b iodegradation data (see Help). Biowin5 and 6 also predict ready biodegradability, but for degradation in the OECD301C test only; using data from the Chemicals Evaluation and Research Institute Japan (CERIJ) database.

### 61

BioHCwin (v1.01) Program Results:

============================== SMILES : O=C(O)Cc(c(c(ccc1)cc2)c1)c2 CHEM : NAPHTHALENEACETIC ACID MOL FOR: C12 H10 O2 MOL WT : 186.21

-------------------------- BioHCwin v1.01 Results

---------------------------

NO Estimate Possible ... Str ucture NOT a Hydrocarbon (Contains atoms other than C, H or S (

- S

- ))

AEROWIN Program (v1.00) Results:

=============================== Sorption to aerosols (25 Dec C)[AEROWIN v1.00]: Vapor pressure (liquid/subcooled): 0.0163 Pa (0.000122 mm Hg ) Log Koa (Koawin est ): 8.993 Kp (particle/gas partition coef. (m3/ug)): Mackay model : 0.000184 Octanol/air (Koa) model: 0.000242 Fraction sorbed to airborne particulates (phi): Junge

- Pankow model : 0.0066 2 Mackay model : 0.0145 Octanol/air (Koa) model: 0.019

AOP Program (v1.92) Results:

=========================== SMILES : O=C(O)Cc(c(c(ccc1)cc2)c1)c2 CHEM : NAPHTHALENEACETIC ACID MOL FOR: C12 H10 O2 MOL WT : 186.21

------------------- SUMMARY (AOP v1.92): HYDROXYL RADICALS (25 deg C)

-------- Hydrogen Abstraction = 0.7005 E

- 12 cm3/molecule

- sec Reaction with N, S and

- OH = 0.5200 E

- 12 cm3/molecule

- sec Addition to Triple Bonds = 0.0000 E

- 12 cm3/molecule

- s ec Addition to Olefinic Bonds = 0.0000 E

- 12 cm3/molecule

- sec Addition to Aromatic Rings = 0.0000 E

- 12 cm3/molecule

- sec Addition to Fused Rings = 35.8273 E

- 12 cm3/molecule

- sec

OVERALL OH Rate Constant = 37.0478 E

- 12 cm3/molecule

- sec HALF

- LI FE = 0.289 Days (12

- hr day; 1.5E6 OH/cm3)
HALF

- LIFE = 3.464 Hrs

------------------- SUMMARY (AOP v1.91): OZONE REACTION (25 deg C)

-----------

****** NO OZONE REACTION ESTIMATION ****** (ONLY Olefins and Acetylen es are Estimated)

Experimental Database: NO Structure Matches Fraction sorbed to airborne particulates (phi): 0.0106 (Junge

- Pankow, Mackay avg) 0.019 (Koa method) Note: the sorbed fraction may be resistant to atmospheric oxidation

KOCWIN Program (v2.00) Results:

============================== SMILES : O=C(O)Cc(c(c(ccc1)cc2)c1)c2 CHEM : NAPHTHALENEACETIC ACID MOL FOR: C12 H10 O2

### 62 Koc may be sensitive to pH!

--------------------------- KOCWIN v2.00 Results

------- --------------------

Koc Estimate from MCI:

---------------------

First Order Molecular Connectivity Index ........... : 6.771
Non

- Corrected Log Koc (0.5213 MCI + 0.60) .......... : 4.1294 Fragment Correction(s):

* Organic Acid (

- CO

- OH) ............... :

- 1.6249 Corrected Log Koc .................................. : 2.5046

Estimated Koc: 319.6 L/kg <===========

Koc Estimate from Log Kow:

------------- ------------

Log Kow (User entered ) ......................... : 2.24
Non

- Corrected Log Koc (0.55313 logKow + 0.9251) .... : 2.1641 Fragment Correction(s):

* Organic Acid (

- CO

- OH) ............... :

- 0.7694 Corrected Log Koc .................................. : 1.3947

Estimated Koc: 24.82 L/kg <===========

******************************************************************** * NOTE: * * The Koc of this structure may be sensitive to pH! The estimated * * Koc represents a best

- fit to the majority of experimental values * * however, the Koc may vary significa ntly with pH. *

********************************************************************

HYDROWIN Program (v2.00) Results:

================================ SMILES : O=C(O)Cc(c(c(ccc1)cc2)c1)c2 CHEM : NAPHTHALENEACETIC ACID MOL FOR: C12 H10 O2 MOL WT : 186.21

--------------------------- HYDROWIN v2.00 Results

---------------------------

Currently, this program can NOT estimate a hydrolysis rate constant for

the type of chemical structure entered!!

ONLY Esters , Carbamates, Epoxides, Halomethanes (containing 1

- 3 halogens), Specific Alkyl Halides & Phosphorus Esters can be estimated!!

When present, various hydrolyzable compound

- types will be identified. For more information, (Click OVERVIEW in Help or see the User's Guide)

***** CALCULATION NOT PERFORMED *****

BCFBAF Program (v3.01) Results:

============================== SMILES : O=C(O)Cc(c(c(ccc1)cc2)c1)c2 CHEM : NAPHTHAL ENEACETIC ACID MOL FOR: C12 H10 O2 MOL WT : 186.21

--------------------------------- BCFBAF v3.01

-------------------------------- Summary Results: Log BCF (regression

- based estimate): 0.50 (BCF = 3.16 L/kg wet

- wt)

### 63 Biotransformation Half

- Life (days) : 1.09 (normalized to 10 g fish)

Log BAF (Arnot

- Gobas upper trophic): 1.26 (BAF = 18.4 L/kg wet

- wt)

Experimental BCF

- kM Database Structure Match:

-------------------------------------------- Name : 1

- Naphthaleneacetic acid CAS Num : 0 00086

- 87

- 3 Log BCF : 0.4674 (BCF = 2.93 L/kg wet

- wt) BCF Data : BCF Ionic Training Set Log Bio HL:

--- Bio Data :

---

Log Kow (experimental): 2.24 Log Kow used by BCF estimates: 2.24 (user entered)

Equation Used to Make BCF estimate: Log BCF = 0.50 (Ionic; Log Kow dependent)

Estimated Log BCF = 0.500 (BCF = 3.162 L/kg wet

- wt)

=========================================================== Whole Body Primary Biotransformation Rate Estimate for Fish:

========================== =================================

------ +

----- +

-------------------------------------------- +

--------- +

--------- TYPE | NUM | LOG BIOTRANSFORMATION FRAGMENT DESCRIPTION | COEFF | VALUE

------ +

----- +

-------------------------------------------- +

-------- - +

--------- Frag | 1 | Aliphatic acid [

- C(=O)

- OH] | 0.3803 | 0.3803 Frag | 1 | Alkyl substituent on aromatic ring | 0.1781 | 0.1781 Frag | 1 | Aromatic

- CH2 |

- 0.3365 |

- 0.3365 Frag | 7 | Aromatic

- H | 0.2664 | 1.8646 Frag | 2 | Number of fused 6

- carbon aromatic rings |

- 0.5779 |

- 1.1557 Frag | 1 | Naphthalene | 0.4320 | 0.4320 L Kow| * | Log Kow = 2.24 (user

- entered ) | 0.3073 | 0.6884 MolWt| * | Molecular Weight Parameter | |

- 0.4775 Const| * | Equation Constant | |

- 1.5058

============+============================================+===== ====+========= RESULT | LOG Bio Half

- Life (days) | | 0.0366 RESULT | Bio Half

- Life (days) | | 1.088 NOTE | Bio Half

- Life Normalized to 10 g fish at 15 deg C |

============+===== =======================================+=========+=========

Biotransformation Rate Constant: kM (Rate Constant): 0.6371 /day (10 gram fish) kM (Rate Constant): 0.3582 /day (100 gram fish) kM (Rate Constant): 0.2015 /day (1 kg fish) kM (Rate Constant): 0.1133 /day (10 kg fish)

Arnot

- Gobas BCF & BAF Methods (including biotransformation rate estimates): Estimated Log BCF (upper trophic) = 1.264 (BCF = 18.37 L/kg wet

- wt) Estimated Log BAF (upper trophic) = 1.264 (BAF = 18. 37 L/kg wet

- wt) Estimated Log BCF (mid trophic) = 1.097 (BCF = 12.49 L/kg wet

- wt) Estimated Log BAF (mid trophic) = 1.097 (BAF = 12.49 L/kg wet

- wt) Estimated Log BCF (lower trophic) = 1.045 (BCF = 11.09 L/kg wet

- wt) Estimated Log BAF (lower trophic) = 1.045 (BAF = 11.1 L/kg wet

- wt)

Arnot

- Gobas BCF & BAF Methods (assuming a biotransformation rate of zero): Estimated Log BCF (upper trophic) = 1.289 (BCF = 19.47 L/kg wet

- wt) Estimated Log BAF (upper trophic) = 1.304 (BAF = 2 0.12 L/kg wet

- wt)

### 64 Volatilization From Water

=========================

Chemical Name: NAPHTHALENEACETIC ACID

Molecular Weight : 186.21 g/mole Water Solubility : 420 ppm Vapor Pressure :

----- Henry's Law Constant: 4.32E

- 009 atm

- m3/mole (estimated by Bond SAR Method)

RIVER LAKE

--------- --------- Water Depth (meters): 1 1 Wind Velocity (m/sec): 5 0.5 Current Velocity (m/sec): 1 0.05

HALF

- LIFE (hours) : 1.849E+005 2.018E+006
HALF

- LIFE (days ) : 7706 8.407E+004
HALF

- LIFE (years) : 21.1 230.2

STP Fugacity Model: Predicted Fate in a Wastewater Treatment Facility

====================================================================== (using 10000 hr Bio P,A,S) PROPERTIES OF: NAPHTHAL ENEACETIC ACID

------------- Molecular weight (g/mol) 186.21 Aqueous solubility (mg/l) 420 Vapour pressure (Pa) 0

(atm) 0 (mm Hg) 0 Henry 's law constant (Atm

- m3/mol) 4.32E

- 009 Air

- water partition coefficient 1.76675E

- 007 Octanol

- water partition coefficient (Kow) 173.78 Log Kow 2.24 Biomass to water partition coefficient 35.556 Temperature [deg C] 25 Biodeg rat e constants (h^

- 1),half life in biomass (h) and in 2000 mg/L MLSS (h):

- Primary tank 0.00 663.91 10000.00

- Aeration tank 0.00 663.91 10000.00

- Settling tank 0.00 663.91 10 000.00

STP Overall Chemical Mass Balance:

--------------------------------- g/h mol/h percent

Influent 1.00E+001 5.4E

- 002 100.00

Primary sludge 6.62E

- 002 3.6E

- 004 0.66 Waste sludge 1.78E

- 001 9.5E

- 004 1.78 Primary volatilization 2.34E

- 006 1.3E

- 008 0.00 Settling volatilization 6.37E

- 006 3.4E

- 008 0.00 Aeration off gas 1.57E

- 005 8.4E

- 008 0.00

Primary biodegradation 1.87E

- 003 1.0E

- 005 0.02 Settling biodegradation 5.59E

- 004 3.0E

- 006 0.01 Aeration biodegradation 7.36E

- 003 4.0E

- 005 0.07

Final water effluent 9.75E+000 5.2E

- 002 97.46

Total removal 2.54E

- 001 1.4E

- 003 2.54 Total biodegradation 9.78E

- 003 5.3E

- 005 0.10

### 65

Level III Fugacity Model (Full

- Output):

======================================= Chem Name : NAPHTHALENEACETIC ACID Molecular Wt: 186.21 Henry's LC : 4.32e

- 009 atm

- m3/mole (Henrywin program) Vapor Press : 9.57e

- 006 mm Hg (Mpbpwin program) Liquid VP : 0.000117 mm Hg (super

- cooled) Melting Pt : 135 deg C (user

- entered) Log Kow : 2.24 (user

- entered) Soil Koc : 320 (KOCWIN MCI method)

Mass Amount Half

- Life Emissions (percent) (hr) (kg/hr) Air 0.0685 6.93 1000 Water 18 360 1000 Soil 81.7 720 1000 Sediment 0.247 3.24e+003 0

Fugacity Reaction Advection Reaction Advection (atm) (kg/hr) (kg/hr) (percent) (percent) Air 1.93e

- 012 148 14.8 4.94 0.493 Water 4.51e

- 014 749 389 25 13 Soil 2.85e

- 013 1.7e+003 0 56.6 0 Sediment 3.56e

- 014 1.14 0.107 0.038 0.00355

Persistence Time: 720 hr Reaction Time: 832 hr Advection Time: 5.35e+003 hr Percent Reacted: 86.5 Percent Advected: 13.5

Half

- Lives (hr), (based upon Biowin (Ultimate) and Aopwin): Air: 6.929 Water: 360 Soil: 720 Sediment: 3240 Biowin estimate: 3.077 (weeks )

Adve ction Times (hr): Air: 100 Water: 1000 Sediment: 5e+004

### 66



## Appendix D . Pending and Active Registrations

Pending and Active Registrations 056001 / 86

- 86

- 2 / 1

- N aphthaleneacetamide

Registration # Registration Name Company # Company Name Current Status % of Active

Ingredient

5481

- 426 AMID

- THIN

- W 5481 AMVAC CHEMICAL CORPORATION 

### Active 8.4

5481

- 431 TECHNICAL 1

-

NAPHTHALENEACETAMIDE 5481 AMVAC CHEMICAL CORPORATION 

### Active 97

Product Mixture

5481

- 473 AMCOTONE

056001 +056002 5481 AMVAC CHEMICAL CORPORATION 

### Active 1.2 /0.45



### Pending and Active Registrations for 056002 / 86

- 87

- 3 / 1

- Naphthaleneacetic acid

Registration # Registration Name Company # Company Name Current Status % of

Active Ingredient

5481

- 219 1

-

NAPHTHALENEACETIC ACID 5481 AMVAC CHEMICAL CORPORATION 

### Active 95.5

5481

- 337 ALCO VITAMIN B

- 1

HORMONE CONCENTRATE 5481 AMVAC CHEMICAL CORPORATION 

### Active 0 .11

5481

- 430 TECHNICAL

NAPHTHALENE ACETIC ACID 5481 AMVAC CHEMICAL CORPORATION 

### Active 95.5

5481

- 473 AMCOTONE

056002+056001 5481 AMVAC CHEMICAL CORPORATION 

### Active 0 .45 /1.2

5481

- 498 1

-

NAPHTHALENEACETIC ACID TECHNICAL 5481 AMVAC CHEMICAL CORPORATION 

### Active 99

73049

- 487 POMAXA PLANT

GROWTH REGULATOR 73049 VALENT BIOSCIENCES CORPORATION 

### Active 3.5

Product Mixtures

### 67

Registration # Registration Name Company # Company Name Current Status % of

Active Ingredient

43905

- 1 WOOD'S ROOTING

COMPOUND With 1.03 % Indole

- 3

- butyric acid 43905 EARTH SCIENCE PRODUCTS CORP. 

### Active 0 .66 /1.03

64388

- 1 DIP'N GROW

With 1.0 % Indole

- 3

- butyric acid 64388 DIP'N GROW, INC. 

### Active 0 .5 /1.0

68719

- 2 VITA GROW READY TO

USE ROOTING COMPOUND With 0.133 % Indole

- 3

- butyric acid 68719 MARCO INDUSTRIES INCORPORATED 

### Active 0 .076 /0.13 3

72594

- O DOC'S LIQUID

CARBON BLOOM With 0.057 % Indole

- 3

- butyric acid and 0.0008 cytokinin 72594 DOC'S PRODUCTS 

### Pending 0 .0057 / 0.0057/ 0.0008

82437

- 1 K & W

AGROCHEMICALS 5

- 15

- 5 WITH GRO

- ROOT LIQUID (GRL) With 0.05% Indole

- 3

- butyric acid 82437 K & W AGRICHEMICAL S, INC. 

### Active 0 .026 /0.05

87394

- 3 K

- L

- N ROOTING

CONCENTRATE With 0.07 % Indole

- 3

- butyric acid 87394 DYNA

- GRO 

### Active 0 .1 /0.07

87394

- 4 ROOT

- GEL With 0.216

% Indole

- 3

- butyric acid 87394 DYNA

- GRO 

### Active .027 /0.216

88031

- 5 GOLDENGRO R With

0.85 % Indole

- 3

- butyric acid and 0.15 % cytokinin 88031 CP BIO, INC 

### Active 0 .2 /0.85/ 0.15

09CA04 800004 CA EPA 

### Pending

Total Rows: 15



### Pending and Active Registrations For 056003 / 15165

- 79

- 4 / P otassium 1

- naphthaleneacetate

Registration # Registration Name Company # Company Name Current Status % of

Active Ingredient

5481

- 413 K

- SALT FRUIT FIX 800 5481 AMVAC CHEMICAL CORPORATION 

### Active 24.2

### 68

Registration # Registration Name Company # Company Name Current Status % of

Active Ingredient

5481

- 414 K

- SALT FRUIT FIX 200 5481 AMVAC CHEMICAL CORPORATION 

### Active 6.25

5481

- LIN AMV1015 5481 AMVAC CHEMICAL CORPORATION 

### Pending 6.25

62097

- GA 1

NAPHTHALENEACETIC ACID TECHNICAL POTASSIUM SALT 62097 FINE AGROCHEMICALS, LTD 

### Pending 95.85

62097

- GI REFINE 24.2L 62097 FINE AGROCHEMICALS, LTD 

### Pending 24.2

62097

- GO REFINE 6.25L 62097 FINE AGROCHEMICALS, LTD 

### Pending 6.25

87320

- 2 REJUVENATE SEED

TREATMENT 87320 STEHEKIN, LLC 

### Active 6.25

OR010002 K

- SALT FRUIT FIX 200 5481 AMVAC CHEMICAL CORPORATION 

### Active 6.25

OR010003 K

- SALT FRUIT FIX 800 5481 AMVAC CHEMICAL CORPORATION 

### Active 24.2

WA010003 K

- SALT FRUIT FIX 800 5481 AMVAC CHEMICAL CORPORATION 

### Active 24.2

WA010004 K

- SALT FRUIT FIX 200 5481 AMVAC CHEMICAL CORPORATION 

### Active 6.25

11ID03 800012 ID Dept. of Agriculture 

### Pending

No Mixtures are Registered at this time

Total Rows: 12



### Pending and Active Registrations For 056004 / 25545

- 89

- 5 / Ammonium 1

- naphthaleneacetate

Registration # Registration Name Company # Company Name Current Status % of Active

Ingredient

5481

- 66 ALCO OLIVE

STOP 5481 AMVAC CHEMICAL CORPORATION 

### Active 5.68

5481

- 129 FRUIT FIX

CONCENTRATE 200 5481 AMVAC CHEMICAL CORPORATION 

### Active 5.68

### 69

Registration # Registration Name Company # Company Name Current Status % of Active

Ingredient

34704

- 382 LIQUI

- STIK

CONCENTRATE 34704 LOVELAND PRODUCTS, INC. 

### Active 5.68

CA100007 LIQUI

- STIK

CONCENTRATE 34704 LOVELAND PRODUCTS, INC. 

### Active 5.68

CA950010 FRUIT FIX

CONCENTRATE 200 5481 AMVAC CHEMICAL CORPORATION 

### Active 5.68

No Mixtures are Registered at this time

Total Rows: 5



### Pending and Active Registrations For 056007 / 61

- 31

- 4 / Sodium 1

- naphthaleneacetate

Registration # Registration Name Company # Company Name Current Status % of

Active Ingredient

5481

- 218 1

-

NAPHTHALENEACETIC ACID SODIUM SALT 5481 AMVAC CHEMICAL CORPORATION 

### Active 93.58

5481

- 427 FRUITONE

- N 5481 AMVAC CHEMICAL CORPORATION 

### Active 3.5

5481

- 541 FRUITONE L 5481 AMVAC CHEMICAL CORPORATION 

### Active 3.5

62097

- GL 1

-

NAPHTHALENEACETIC ACID TECHNICAL SODIUM SALT 62097 FINE AGROCHEMICALS, LTD 

### Pending 97.5

62097

- GT REFINE 3.5 WSG 62097 FINE AGROCHEMICALS, LTD 

### Pending 3.5

73049

- 488 NA+NAA TECHNICAL

PLANT GROWTH REGULATOR 73049 VALENT BIOSCIENCES CORPORATION 

### Active 95.1

73049

- 489 1

- NAPHTHYLACETIC

ACID TECHNICAL 73049 VALENT BIOSCIENCES CORPORATION 

### Active 99

11ID04 800012 ID Dept. of Agriculture 

### Pending

No Mixtures are Registered at this time

Total Rows: 8

### 70

Pending and Active Registrations For 056008 / 2122

- 70

- 5 / Ethyl 1

- naphthaleneacetate

Registration # Registration Name Company # Company Name Current Status % of

Active Ingredient

5481

- 429 TRE

- HOLD SPROUT

INHIBITOR A

- 112 5481 AMVAC CHEMICAL CORPORATION 

### Active 15.1

5481

- 433 TECHNICAL 1

-

NAPHTHALENEACETIC ACID, ETHYL ESTER 5481 AMVAC CHEMICAL CORPORATION 

### Active 95

5481

- 452 TRE

- HOLD RTU

SPROUT INHIBITOR 5481 AMVAC CHEMICAL CORPORATION 

### Active 1.15

5481

- 460 TRE

- HOLD SPROUT

INHIBITOR FOR RESIDENTIAL USE 5481 AMVAC CHEMICAL CORPORATION 

### Active 1.15

CA930013 TRE

- HOLD SPROUT

INHIBITOR A112 5481 AMVAC CHEMICAL CORPORATION 

### Active 15.1

OR070005 TRE HOLD SPROUT

INHIBITOR 5481 AMVAC CHEMICAL CORPORATION 

### Active 1.15

11CA02 800004 CA EPA 

### Pending
No Mixtures are Registered at this time

Total Rows: 7

### 71

APPENDIX E

Site/Pest Information For

056001 / 86

- 86

-

2 / 1

- Naphthaleneacetamide

Site Name Status Status Date Registration # APPLES (FOLIAR TREATMENT) Approved 1960, 1998 5481

- 426

, 5481

- 473 AZALEA (CUTTINGS) Approved 09

- May

- 1989 264

- 499 BARBERRY (CUTTINGS) Approved 09

- May

- 1989 264

- 499 BEGONIA (CUTTINGS) Approved 09

- May

- 1989 264

- 499 BOXWOOD (CUTTINGS) Approved 09

- May

- 1989 264

- 499 CHRYSANTHEMUM (CUTTINGS) Approved 09

- May

- 1989 264

- 499 CRAPE MYRTLE (CUTTINGS) Approved 09

- May

- 1989 264

- 499 EUONYMUS (CUTTINGS) Approved 09

- May

- 1989 264

- 499
FORMULATING USE ONLY NO SITE Approved 19

- Aug

- 1982 5481

- 431 FORSYTHIA (CUTTINGS) Approved 09

- May

- 1989 264

- 499 FUCHSIA (CUTTINGS) Approved 09

- May

- 1989 264

- 499 GERANIUM (CUTTINGS) Approved 09

- May

- 1989 264

- 499 HOLLY (CUT PLANT MATERIAL) Approved 09

- May

- 1989 264

- 499 IVY (CUTTINGS) Approved 09

- May

- 1989 264

- 499 JUNIPER (CUTTINGS) Approved 09

- May

- 1989 264

- 499 LILAC (CUTTINGS) Approved 09

- May

- 1989 264

- 499 PACHYSANDRA (CUTTINGS) Approved 09

- May

- 1989 264

- 499 PEARS (FOLIAR TREATMENT) Approved 1960, 1998 5481

- 426

, 5481

- 473 PEARS (FOLIAR TREATMENT) Approved 11

- Dec

- 1998 5481

- 473 PEARS (BARTLETT) (FOLIAR TREATMENT) Approved 10

- Nov

- 1960 5481

- 426 PEARS (BOSC) (FOLIAR TREATMENT) Approved 10

- Nov

- 1960 5481

- 426 PRIVET (CUTTINGS) Approved 09

- May

- 1989 264

- 499 PYRACANTHA (CUTTINGS) Approved 09

- May

- 1989 264

- 499 RHODODENDRON (CUTTINGS) Approved 09

- May

- 1989 264

- 499 ROSES (CUT PLANT MATERIAL) Approved 09

- May

- 1989 264

- 499 SPIREA (CUTTINGS) Approved 09

- May

- 1989 264

- 499

TANK MIX Approved 11

- Dec

- 1998 5481

- 473 TAXUS (YEW) (DELAYED DORMANT APPLICATION) Approved 09

- May

- 1989 264

- 499

VIBURNUM (CUTTINGS) Approved 09

- May

- 1989 264

- 499



### Site/Pest Information For 056002 / 86

- 87

- 3 / 1

- Naphthaleneacetic acid

Site Name Status Status Date Registration #

AVOCADOS Pending 2009 , 2013 09CA04

, 13CA08
HERBS (FOLIAR TREATMENT) Pending 09

- Apr

- 2003 72594

- L
, 72594

- U

HERBS (FOLIAR TREATMENT) Pending 09

- Apr

- 2003

ORNAMENTAL FLOWERING PLANTS , TREES AND SHRUBS (FOLIAR and CUTTING TREATMENT s ) African violets, Ajuga, Allyssum, Aster, Azalea, Barberry, Begonia, Non

- bearing Berry, Boxwood, Camellia, Chrysanthemum, Clematis, Crape myrtle, Pending 09

- Apr

- 2003 72594

- L
, 72594

- U
, 72594

- O

### 72 Dahlias, Delphinium, Dianthus, Euonymous, Firethorn, Forsythia, Fuschia, Gardenia, Geranium, Hibiscus, Honeysu ckle, Ivy, Jasmine, Junioer, Lilac, Myrtle, Pachysandra

ORNAMENTAL PLANTS (CUTTINGS) Pending 07

- Jul

- 2010 87394

- E
, 87394

- 4
VEGETABLE CROPS (FOLIAR TREATMENT) Pending 09

- Apr

- 2003 72594

- L
, 72594

- U CACTI (CUTTINGS) Approved 19

- Jun

- 2009 64388

- 1 CITRUS (NONBEARING and TRANSPLNTS ) Approved 22

- Aug

- 2002 72639

- 11

CYPRESS (FOLIAR /CUTTINGS TREATMENT) Approved 07

- Jan

- 2005 75851

- 1

DATE PALM Approved 29

- Jul

- 2011 88031

- 5 DATES (NONBEARING) Approved 22

- Aug

- 2002 72639

- 11
DATES (NONBEARING) Approved 28

- Nov

- 2007 83028

- 11 DOGWOOD (FOLIAR /CUTTING TREATMENT) Approved 07

- Jan

- 2005 75851

- 1

DOUGLAS

- FIR (CUTTINGS) Approved 10

- Jul

- 2009 82437

- 1 GOOSEBERRIES (FOLIAR TREATMENT) Approved 20

- Jun

- 2000 5481

- 498
GOOSEBERRIES (DELAYED DORMANT APPLICATION) Approved 20

- Jun

- 2000 5481

- 498 GOOSEBERRIES (POSTHARVEST APPLICATION TO PLANTS) Approved 20

- Jun

- 2000 5481

- 498 GRAPES (NONBEARING) Approved 22

- Aug

- 2002 72639

- 11
GRAPES (TRANSPLANTS) Approved 28

- Nov

- 2007 83028

- 11

GREENHOUSES Approved 24

- May

- 2012 87394

- 3 HAWTHORN (CUTTINGS) Approved 10

- Jul

- 2009 82437

- 1
HEATHER (FOLIAR /CUTTING TREATMENT) Approved 07

- Jan

- 2005 75851

- 1 HOLLY (FOLIAR /CUTTING TREATMENT) Approved 07

- Jan

- 2005 75851

- 1 JAPANESE QUINCE (CUTTINGS and FOLIAR ) Approved 28

- Nov

- 2007 83028

- 11
MAGNOLIA (FOLIAR /CUTTING TREATMENT) Approved 07

- Jan

- 2005 75851

- 1 NURSERY STOCK (FOLIAR TREATMENT) Approved 07

- Jan

- 2005 75851

- 1 NUT TREES (NONBEARING) Approved 22

- Aug

- 2002 72639

- 11

OAK (CUTTINGS) Approved 10

- Jul

- 2009 82437

- 1 PEARS (FOLIAR TREATMENT) Approved 11

- Dec

- 1998 5481

- 473 PINE (CUTTINGS) Approved 10

- Jul

- 2009 82437

- 1
POME FRUITS (NONBEARING) Approved 22

- Aug

- 2002 72639

- 11 POPLAR (CUTTINGS) Approved 10

- Jul

- 2009 82437

- 1

STONE FRUITS (NONBEARING) Approved 22

- Aug

- 2002 72639

- 11
VEGETABLE GARDEN CROPS (FOLIAR TREATMENT) Approved 07

- Jan

- 2005 75851

- 1



### Site/Pest Information For 056003 / 15165

- 79

- 4 / Potassium 1

- naphthaleneacetate

Site Name Status Status Date Registration # POTATOES (SEED TREATMENT) Pending 04

- Apr

- 2011 11ID03
AERIAL APPLICATION Approved 24

- Jan

- 1961 5481

- 428 APPLES (FOLIAR TREATMENT) Many Varieties Approved 24

- Jan

- 1961 5481

- 428 CITRUS (FOLIAR TREATMENT) Approved 16

- Mar

- 1990 5481

- 414 HOLLY (CUT PLANT MATERIAL) Approved 16

- Mar

- 1990 5481

- 414 HOLLY (CUTTINGS) Approved 10

- Jul

- 2000 5481

- 497 MANDARIN (FOLIAR TREATMENT) Approved 16

- Mar

- 1990 5481

- 414
OLIVES (FOLIAR TREATMENT) Approved 16

- Mar

- 1990 5481

- 414 ORANGES (FOLIAR TREATMENT) Approved 16

- Mar

- 1990 5481

- 414

### 73 PEARS (FOLIAR TREATMENT) Multiple Varieties Approved 24

- Jan

- 1961 5481

- 428 POTATOES (SEED TREATMENT) Approved 08

- May

- 2012 87320

- 2 TANGELOS (FOLIAR TREATMENT) Approved 16

- Mar

- 1990 5481

- 414
TANGERINES (FOLIAR TREATMENT) Approved 10

- Jul

- 2000 5481

- 497 TANGOR (FOLIAR TREATMENT) Approved 16

- Mar

- 1990 5481

- 414
TANK MIX Approved 23

- Oct

- 1990 5481

- 413



### Site/Pest Information For 056004 / 25545

- 89

- 5 / Ammonium 1

- naphthaleneacetate

Site Name Status Status Date Registration #
AERIAL APPLICATION Approved 30

- Jul

- 1964 34704

- 382
APPLES (FOLIAR TREATMENT) Approved 30

- Jul

- 1964 34704

- 382 CHERRIES (SWEET) (FOLIAR TREATMENT) Approved 11

- Oct

- 1995 CA950010 MANDARIN (FOLIAR TREATMENT) Approved 22

- Jan

- 1974 5481

- 130 OLIVE (ORNAMENTAL) (FOLIAR TREATMENT) Approved 02

- May

- 1969 5481

- 66 OLIVES (FOLIAR TREATMENT) Approved 22

- Jan

- 1974 5481

- 130 OLIVES (SEED CROP FOLIAR TREATMENT) Approved 30

- Jul

- 1964 34704

- 382 ORANGES (FOLIAR TREATMENT) Approved 22

- Jan

- 1974 5481

- 130 PEAR (ORNAMENTAL) (FOLIAR TREATMENT) Approved 02

- May

- 1969 5481

- 66 PEARS (FOLIAR TREATMENT) Multiple varieties Approved 30

- Jul

- 1964 34704

- 382 PLUM (ORNAMENTAL) (FOLIAR TREATMENT) Approved 02

- May

- 1969 5481

- 66 TANGELOS (FOLIAR TREATMENT) Approved 22

- Jan

- 1974 5481

- 130 TANGERINES (FOLIAR TREATMENT) Approved 22

- Jan

- 1974 5481

- 130
TANGOR (FOLIAR TREATMENT) Approved 22

- Jan

- 1974 5481

- 130



### Site/Pest Information For 056007 / 61

- 31

- 4 / Sodium 1

- naphthaleneacetate

Site Name Status Status Date Registration #

POTATOES Pending 04

- Apr

- 2011 11ID04
AERIAL APPLICATION Approved 19

- Jan

- 1961 5481

- 427 APPLES (FOLIAR TREATMENT) Multiple Varieties Approved 19

- Jan

- 1961 5481

- 427 CATALPA (FOLIAR TREATMENT) Approved 13

- Feb

- 1987 34704

- 360 CRABAPPLES (FOLIAR TREATMENT) Approved 29

- May

- 2013 5481

- 541 ELM (FOLIAR TREATMENT) Approved 13

- Feb

- 1987 34704

- 360 HORSECHESTNUT (FOLIAR TREATMENT) Approved 13

- Feb

- 1987 34704

- 360 JAPANESE QUINCE (FOLIAR TREATMENT) Approved 29

- May

- 2013 5481

- 541 LOQUAT (FOLIAR TREATMENT) Approved 29

- May

- 2013 5481

- 541 LOW VOLUME APPLICATION (ALL OR UNSPECIFIED) Approved 05

- Apr

- 2005 WA050004 MAPLE (FOLIAR TREATMENT) Approved 13

- Feb

- 1987 34704

- 360 OLIVES (FOLIAR TREATMENT) Approved 13

- Feb

- 1987 34704

- 429 PEARS (FOLIAR TREATMENT) Multiple Varieties Approved 19

- Jan

- 1961 5481

- 427 QUINCES (FOLIAR TREATMENT) Approved 29

- May

- 2013 5481

- 541

TANK MIX Approved 03

- Aug

- 2007 5481

- 541

### 74 Site/Pest Information For 056008 / 2122

- 70

- 5 / Ethyl 1

- naphthaleneacetate

Site Name Status Status Dat e Registration #

AVOCADOS Pending 20

- Mar

- 2012 12CA05 AMERICAN ELM (FOLIAR TREATMENT) Approved 05

- Dec

- 1980 5481

- 429 AMERICAN ELM (PRUNE/WOUND TREATMENT) Approved 03

- Apr

- 1995 5481

- 452 APPLES (BARK TREATMENT) Approved 03

- May

- 1991 5481

- 434 APPLES (DORMANT) Approved 05

- Dec

- 1980 5481

- 429 APPLES (NONBEARING) Approved 05

- Dec

- 1980 5481

- 429 AVOCADOS (DORMANT APPLICATION) Approved 29

- May

- 2013 5481

- 429
BLACK WILLOW (FOLIAR, PRUNE, BARK TREATMENT) Approved 03

- May

- 1991 5481

- 434 CAROB (ORNAMENTAL) (PRUNE/WOUND TREATMENT) Approved 03

- Apr

- 1995 5481

- 452 CHINESE ELM (FOLIAR, BARK, PRUNE TREATMENT) Approved 05

- Dec

- 1980 5481

- 429 CHRISTMAS TREE PLANTINGS (FOLIAR TREATMENT) Approved 09

- May

- 2007 OR070005 CITRUS (NONBEARING) (BARK, PRUNING TREATMENT) Approved 03

- May

- 1991 5481

- 434 COAST REDWOOD (BARK , FOLIAR, PRUNING TREATMENT) Approved 03

- May

- 1991 5481

- 434 CRABAPPLE (ORNAMENTAL) (BARK/PRUNING TREATMENT) Approved 03

- May

- 1991 5481

- 434 CRABAPPLES (FOLIAR or DORMANT TREATMENT) Approved 05

- Dec

- 1980 5481

- 429 CRAPE MYRTLE (FOLIAR, BARK, PRUNING TREATMENT) Approved 05

- Dec

- 1980 5481

- 429 FLOWERING PLUM (PRUNE/WOUND TREATMENT) Approved 03

- Apr

- 1995 5481

- 452 JAPANESE QUINCE (DORMANT APPLICATION) Approved 29

- May

- 2013 5481

- 429 LOQUAT (DORMANT APPLICATION) Approved 29

- May

- 2013 5481

- 429 MAMEY SAPOTE (DORMANT APPLICATION) Approved 29

- May

- 2013 5481

- 429 MANGOS (DORMANT APPLICATION) Approved 29

- May

- 2013 5481

- 429 NECTARINES (BARK, PRUNING TREATMENT) Nonbearing and bearing? Approved 03

- May

- 1991 5481

- 434

NOBLE FIR (CHRISTMAS TREE PLANTINGS) (FOLIAR TREATMENT) Approv ed 09

- May

- 2007 OR070005

NORDMAN FIR (FOLIAR TREATMENT) Approved 09

- May

- 2007 OR070005 OLIVES (BARK, PRUNING and DORMANT TREATMENT) Approved 03

- May

- 1991 5481

- 434 ORIENTAL PEAR (DORMANT APPLICATION) Approved 29

- May

- 2013 5481

- 429 ORNAMENTAL FLOWERING and SHADE TREES (FOLIAR TREATMENT) Approved 05

- Dec

- 1980 5481

- 429

ORNAMENTAL WOODY PLANTS and SHRUBS (DORMANT APPLICATION) Approved 05

- Dec

- 1980 5481

- 429

PEARS (BARK TREATMENT) DORMANT Approved 03

- May

- 1991 5481

- 434 PEARS (NONBEARING) Approved 05

- Dec

- 1980 5481

- 429 PEARS (PRUNE/WOUND TREATMENT) Approved 03

- May

- 1991 5481

- 434
POMEGRANATES (NONBEARING) Approved 26

- Oct

- 1993 CA930013 PUSSY WILLOW (FOLIAR TREATMENT) Approved 05

- Dec

- 1980 5481

- 429 PYRACANTHA (FOLIAR/ BARK/PRUNING TREATMENT) Approved 05

- Dec

- 1980 5481

- 429 QUINCES (DORMANT APPLICATION) Approved 29

- May

- 2013 5481

- 429 RED MAPLE (BARK, FOLIAR, PRUNING TREATMENT) Approved 03

- May

- 1991 5481

- 434 RIVER BIRCH (PRUNE/WOUND TREATMENT) Approved 03

- Apr

- 1995 5481

- 452 SILVER MAPLE (FOLIAR , BARK or PRUNING TREATMENT) Approved 05

- Dec

- 1980 5481

- 429
SUGAR MAPLE (FOLIAR , BARK or PRUNING TREATMENT) Approved 05

- Dec

- 1980 5481

- 429 SYCAMORE (FOLIAR , BARK or PRUNING TREATMENT) Approved 05

- Dec

- 1980 5481

- 429 WATER OAK (FOLIAR , BARK or PRUNING TREATMENT) Approved 03

- May

- 1991 5481

- 434
WAX

- MYRTLE (PRUNE/WOUND TREATMENT) Approved 03

- Apr

- 1995 5481

- 452 WILLOW (BARK or PRUNING TREATMENT) Approved 03

- May

- 1991 5481

- 434