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-napthaleneacetic acid (NAA), 

and its sodium, potassium and ammonium salts, ethyl ester and acetamide (Table 1). The 

problem formulation describes the methods to be used during the completion of drinking water 

and ecological risk assessments in support of registration review and provides an overview of the 

environmental fate, ecological effects, and potential risks associated with the use of NAA as well 

as uncertainties unique to risk assessment of NAA, and its salts, ester and acetamide. This 

document also identifies additional studies that would be beneficial to the conduct of an 

ecological risk assessment. Major findings include the following.

Stressors of Concern

Inspection of the product labels shows that the products containing 1-napthaleneacetic 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-sprouting.” Given the limited 

exposure expected for the ethyl ester compared to other chemicals 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 forms.

Environmental Fate Data Gaps

Physical 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 respect 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 (835.4100 with 1-napthalene acetic acid (NAA) and naphthalene 

acetamide): 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 completely to the acid. If this 

is not the case, then an 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 with 1-napthalene acetic acid (NAA) and 

naphthalene acetamide): 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 and 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 

requested for one of the salts. In the absence of data, the Agency will assume that the chemicals 

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 European Commission. According to the European Commission (EC) Draft Assessment 

Report1dated August 2008, the DT50’s2for the total system in two sediments are 6.2 and 9.5 days. 

Should it comply with Agency guidance, this study should be submitted to the Agency. If found 

acceptable or supplemental, the study may be used in the forthcoming Preliminary Ecological 

Risk Assessment.

Adsorption/Desorption (Batch Equilibrium) (835.1230 with 1-napthalene acetic acid (NAA)

and naphthalene acetamide): 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 two 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 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 soluble and dissociate completely to the acid. If this is not the case, then an 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 available for the 

acid. This study was submitted to the EC and is cited in the EC Draft Assessment Report. 

According to the EC report, naphthalene acetic acid’s Kd values range from 0.40 to 2.72 cm3/g (or 

mL/g), KOC values range from 68.5 to 138 cm3/gOC, KF values range from 0.297 to 1.77 cm3/g, 

and KFOC values range from 50.3 to 88.5 cm3/gOC. Should it comply with Agency guidance, this

study should be submitted to the Agency. If the study is found to be acceptable or supplemental, 

it may be used in the Preliminary Risk Assessment.

Environmental Chemistry Method and Associated Independent Laboratory Validation 

(Water) (850.6100 with 1-napthalene acetic acid (NAA) and naphthalene acetamide): An 

environmental chemistry method (ECM) and its associated independent 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 sediment has not been deemed necessary 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 Bee Adult Acute Contact Toxicity (850.3020 with TGAI 1-naphthaleneacetic acid):

Currently 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 submitted to the Agency. If it is 

found to be acceptable or supplemental, it may be used in the Preliminary Risk Assessment.

Honey Bee Adult Acute Oral Toxicity (Non-Guideline Special Study, OECD 213 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 adult honey bees resulting from acute 

oral exposure 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 Bee 10 day Adult Chronic Toxicity (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 residues 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 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 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 acetamide. No data have been 

submitted on the chronic toxicity 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 (aminopyralid, 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 (850.4500 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 needed 
5

using the NAA and the amide form of NAA. The 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 be acceptable or supplemental, they may be used 

in the Preliminary Risk Assessment.

Acute Toxicity to Freshwater and Saltwater Fish (850.1075) with the TGAI 

Naphthaleneacetamide. 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, 850.1035) with the 

TGAI Naphthaleneacetamide. For freshwater and saltwater invertebrates, 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).

Chronic Toxicity to Freshwater Fish (850.1400) with the TGAI Naphthalene Acetamide. 

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 

Naphthaleneacetamide. 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 compounds 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, quantitative structure activity relationships (QSAR) and limited available data 

were used to derive some of the input parameters for the aquatic models. Major uncertainties 

with respect 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 CATABOL3program 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 Tables 2a to 2d (as 

shown in footnotes to the tables), 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 its 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. Although 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. 

The 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 conducted 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 purposes regarding risk to honeybees, chronic 

toxicity to aquatic organisms, and acute 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 

root 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. 2002). NAA and related 

compounds are formulated as six different active ingredients listed in Table 1.

Table 1. Chemical structures of Naphthalene acetic acid and related active ingredients1

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 20oC

 

3 CATABOL is a model that predicts degradation pathways of a chemical in the presence of mixed population of 

environmental microorganisms (source: OECD 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 20oC

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 oC

SMILES Code: c12c(cccc1CC(N)=O)cccc2

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

Solubility 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 association with the updated toxicity, exposure, and usage 

information. In 2004, EFED conducted an ecological risk assessment in support of a Revised 

Registration Eligibility Document for all uses of napthaleneacetic acid and related compounds 
8

(D306433 dated 10/26/04). In 2011, a FIFRA Section 18 emergency exemption was granted for 

the product Rejuvenate Seed Treatment, containing potassium naphthaleneacetate, on potato 

seeds, and the product Mitigate PGR4, containing sodium naphthaleneacetate, on potato foliage in 

Idaho (D376108). A FIFRA Section 3 new use assessment was also conducted in 2011 for the 

use of potassium naphthaleneacetate and sodium naphthaleneacetate on potato seeds and/ or on 

potato foliage for the new products RenewTM PGR and RenewTM Concentrate PGR (D388693+). 

The latest risk assessment was issued in 2012 (D402377), for 1-naphthaleneacetic acid (NAA), 

sodium naphthaleneacetate, and ethyl naphthaleneacetate uses on certain tropical fruits (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 rambutan, avocado, mamey sapote,

and mango 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 and acetamide.

The latest crop use map for NAA was 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. The map in Figure 1 included only the napthalene acetic acid. The map for napthalene

acetamide (which is not included below) shows that it is used more prominently in the Pacific

Northwest areas of U.S. and California. 

 

4 PGR=Plant Growth Regulator.

5 The abbreviation 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 

potassium 1-naphthaleneacetate, 5 products for ammonium 1-naphthaleneacetate, 5 products for 

sodium 1-naphthaleneacetate and 5 products for ethyl 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 

applied 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 fruit 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 aerial applications 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, Christmas 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 2a. Uses Site 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 NO.

OF APPS.

AT MAX 

RATE

SEASONAL 

APP. RATE 

(lb A.E./A)1

MINIMUM 

INTERVAL 

BETWEEN 

APPS. (days)

APP.

METHOD1

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)

ND NS ND 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 NO.

OF APPS.

AT MAX 

RATE

SEASONAL 

APP. RATE 

(lb A.E./A)1

MINIMUM 

INTERVAL 

BETWEEN 

APPS. (days)

APP.

METHOD1

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 Where 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 RED, 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 

APPS. (days)

APP.

METHOD1

INCORP. 

DEPTH 

(inches)

Rambutan 0.11 1 0.112 5 TP 0

Citrus (mandarin, oranges, tangelos, 

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, nonflowering 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: Azarole, 

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 0.00043 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); TP = treat 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 treatment 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; accessed June 16, 2014).
12

Table 2c. Uses Site and Application Information for Napthalene Acetamide, based on the 

2007 Revision of the RED, 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 

APPS. (days)

APP.

METHOD1

INCORP. 

DEPTH 

(inches)

Ornamental plants (herbaceous, 

woody shrubs and vines), shade 

trees, and ornamental trees

0.112 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 information 

provided in the table was derived from the RED amendment document.

Table 2d. Uses Site and Application Information for Ethyl 1-Napthaleneacetate, based on 

the 2007 Revision of the RED, 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 

APPS. (days)

APP.

METHOD1

INCORP. 

DEPTH 

(inches)

Apples 0.11 3 0.33 5 B 0

Olives 0.33 1 0.33 N/A B 0

Ornamental Citrus, Pomegranate and 

Nectarine (nectarine is disallowed in 

CA)

0.11 3 0.33 5 B 0

Ornamental 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 and Cultivars, 

Varieties and/or hybrids of these 

trees

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.

According to the 2007 Reregistration Eligibility Decision document, the following label 

restrictions were imposed to the naphthalene acetic acid and derivatives 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 Speed Restriction:

"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 nozzles.”

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 did not present significant potential for risks to birds, mammals, 

fish, aquatic invertebrates, or aquatic plants. However, an assessment based on conservative 

exposure assumptions indicated that endangered terrestrial plants may be at risk. Risks to 

terrestrial insects could not be quantified due to lack of toxicity 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 these three active ingredients on avocado (D361448, April 13, 2009). In that 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 the 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 Persistent

Degrades 

of Concern

No No Yes ND No No No No No No ND

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; ND = 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, and ethyl 1-naphthaleneacetate on 

certain tropical fruits and pome fruits. Previously the only pome fruits included on the labels 

were apples and pears. The proposed new uses on rambutan, avocado, mamey sapote, and mango

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 its derivatives, it was found that olives still represented

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 D387171). 

Therefore, the drinking water assessment results did 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 

(MODEL 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 surface 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, no Total Maximum Daily Load (TMDL) criteria have been developed for 

napthalene 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 

07/25/14. 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 07/25/14.) 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 C12H10O2 – –

Molecular Weight 186.21 2007 RED Also in HSDB

Water Solubility

420 mg/L for NAA (26

oC)

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 HSDB1

Vapor Pressure (25oC)

0.3 Torr for NAA MRID 40522903

Considered 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 Torr for NAA EPISUITE v.4.1 –

Henry’s Law constant 1.75 x 10-4 atm-m3

/mol Calculated

Calculated from vapor pressure

(0.3 Torr) 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 dissociated 

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 HSDB2 –

174 (Log KOW = 2.24)

EPISUITE v.4.1 

and HSDB3 –
16

PARAMETER VALUE(S) (units) SOURCE COMMENT

Octanol-Water Partition 

Coefficient (KOW,

unspecified temperature)

2.29x103(Log KOW = 3.36) for the 

ethyl ester MRID 47505902 –

Hydrolysis Half-life 

(pH 5, 7, 9)

NAA: stable; there are no 

hydrolyzable functional groups.

Acc. No. 

00129382

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

HSDB5

Photolysis may be an important 

process following exposure of an 

aqueous solution of NAA to 4 

days of sunlight 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. HSDB6

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. This study was not 

available for review.

Photolysis in Air t1/2 = 0.289 days EPISUITE v.4.1 Hydroxyl radical reactions

Aerobic Soil Metabolism 

Half-life t1/2 = 10 days HSDB7

Half-life attributed to microbial 

degradation. The cited study was 

not available for review.

Organic Carbon Partition

Coefficient (KOC) 24.82 mL/gOC EPISUITE v.4.1

Anions generally do not adsorb 

more strongly to organic carbon 

and clay than their neutral 

counterparts. KOC 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 concentrations of 0.5 

and 0.05 mg/l, respectively. HSDB8

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), 1291-

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 (1994)

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 generally short lived and may show mobility in the environment, based on 

values 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 fields 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 to 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 hours for NAA, 131.6 hours for 1-naphthalene-acetamide, and 12.8 hours for 

NAA ethyl ester (MRID No. 43482101). 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-m3/mol because its solubility is high. Abiotic dissipation processes

may also contribute to NAA’s rapid dissipation from foliage (i.e., photolysis).

Naphthalene 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 266 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) reported 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-life of 4 days for modeling purposes. According to the 

HSDB, on soils, under aerobic conditions, NAA exposure to UV and sunlight produced 1-

hydroxymethyl naphthalene, 1-naphthaldehyde, naphthalene-1-carboxylic acid, and 1-methylnaphthalene. Only the 1-methyl-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 

proceed with a half-life of around 0.3 days (EPISUITE 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 attributed to microbial degradation; however, this study was not available for review by the 

Agency. For NAA, EPISUITE’s KOCWIN predicts a KOC value of 24.8 L/kgOC. NAA is mobile 

according to the FAO mobility classification (FAO 2000).

Per the HSDB, for 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 KOW

for NAA of 174.

There are considerable uncertainties in this problem formulation due 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

There 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 

CO2) to yield 1-methyl-naphthalene, and subsequently oxidation 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 terrestrial 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, 

respectively. 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 LC50 or EC50 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, EC50

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 Most Sensitive Aquatic Toxicity Endpoints for Napthalene acetic acid or 

its salts

Taxonomic

Group Study Type Surrogate Species Chemical (Form)

Toxicity 

Value

Acute Toxicity 

Classification 

(MRID)

Freshwater Fish1

Acute

Rainbow trout,

Oncorhynchus 

mykiss 

NAA

(98% TGAI)

96-h LC50 = 28 

mg ai/L

Slightly toxic 

(00082528, 

acceptable)

NAA

(15.1% 

Formulation)

96-h LC50 = 14 

mg ai/L

Slightly Toxic 

(00042756; 

supplemental)

Chronic Data gap2

Freshwater 

invertebrates

Acute Water flea

Daphnia magna

NAA

(TGAI)

48-h EC50 = 

180 mg ai/L

Practically Nontoxic (00082526 

Acceptable)

Chronic Data gap2

Estuarine/marine 

fish

Acute Data gap2

Chronic Data gap2

Estuarine/marine 

invertebrates

Acute Data gap2

Chronic Data gap2

Aquatic plants 

and algae

Vascular Duckweed, Lemna 

gibba

Potassium salt 

of NAA (24.2% 

formulation)

14-d EC50 = 

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.)

EC50 = 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 factor 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 EC50 values of 23.8 vs. 5.68 mg ai/L, 

respectively). 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 Most Sensitive Aquatic Toxicity Endpoints for 1-naphthaleneacetamide 

and Napthalene acetic acid ethyl ester 

Taxonomic 

Group Study Type Surrogate Species Chemical (Form) Toxicity Value

Acute Toxicity 

Classification 

(MRID)

Freshwater Fish1

Acute

Bluegill sunfish, 

Lepomis 

macrochirus

NAA ethyl 

ester

(TGAI)

96-h LC50 = 

2.68 mg ai/L

Moderately toxic 

(42498101, 

acceptable)

Chronic Data gap2

Freshwater 

invertebrates

Acute Water flea

Daphnia magna

NAA ethyl ester

(TGAI)

48-h EC50 = 5.68 

mg ai/L

Moderately 

Toxic 

(42470801, In 

Review)

NAA ethyl ester

(Formulation)

48-h EC50 = 23.8 

mg ai/L

Moderately 

Toxic 

(00042755, 

Supplemental)

Chronic Data gap2

Estuarine/marine 

fish

Acute Data gap2

Chronic Data gap2

Estuarine/marine 

invertebrates

Acute Data gap2

Chronic Data gap2

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 for 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 2004 

RED assessment; D306433). For freshwater fish and invertebrates, acute RQ values of 7 x 10-5

and 4 x 10-4 were calculated. 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 analysis 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 

LC50

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 

LC50

--- 1,174 35.3 --- 97 --- 3.7

SW Fish Chronic --- 148 4.5 --- --- --- 0.73

FW Invert (D. magna) 

Acute 48-h EC50

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 

LC50

--- 742 247 --- 5.4 --- 1.6

SW Invert (Mysid 

Shrimp) Chronic --- 59.7 19.9 --- --- --- 3.2

Green Algae 96-h EC50 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. Adjustment 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 invertebrates (following 

adjustment based on measured data) are three to four orders of magnitude greater than the 

previously estimated aquatic EECs (0.012 – 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 margins 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 forms of NAA with green algae, toxicity data were only submitted for one 

algal species. Given the mode of action of NAA and sensitivity differences 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 naphthaleneacetamide 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 submitted toxicity data for naphthaleneacetamide

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 forthcoming 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 assessment. 

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 

reproduction 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 LD50 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 honey 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 guidance6.

 

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 data that can be used to assess the effect of

naphthaleneacetamide on terrestrial plants is recommended. 

Table 8. Summary of the Most Sensitive Endpoints from Terrestrial Toxicity Studies for 

Napthalene acetic acid and associated salts

Taxonomic 

Group

Study Type Surrogate 

Species

Chemical 

(form)

Toxicity Value Acute Toxicity 

Classification 

(MRID) 

Birds1

Acute oral

Mallard duck, 

Anas 

platyrhynchos

NAA (TGAI, 

97%)

LD50 = 1750 mg 

ai/kg-bw

Slightly toxic 

(00065839, 

supplemental) 

NAA 

(Formulation, 

15.1%)

LD50 > 2,150 mg 

ai/kg-bw

Practically nontoxic 

(00042754, 

Supplemental)

Sub-acute 

dietary

Bobwhite quail, 

Colinus 

virginianus

NAA (TGAI)

8-d LC50

>10,000 mg ai/kgdiet

Practically nontoxic 

(00085909, 

supplemental)

NAA 

(Formulation, 

15.1%)

8-d LC50

>10,000 mg ai/kgdiet

Practically nontoxic 

(42584202, 

acceptable)

Chronic Bobwhite quail

or Mallard duck Data gap

Mammals

Acute Oral

Laboratory rat 

(Rattus 

norvegicus)

NAA (TGAI) 

LD50 = 933 

mg/Kg

LD50 = 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)

EC25 = 0.015 lb 

ai/A

NOAEC = 0.011 

lb ai/A

 43803201

Monocot –

wheat

NAA Potassium 

salt 

(formulation)

EC25 = 0.075 lb 

ai/A

NOAEC = 0.02 lb 

ai/A

43803201

Terrestrial 

plants

Vegetative 

vigor

Dicot – Tomato NAA Potassium 

salt 

(formulation)

EC25 = 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 birds are used as surrogates for terrestrial-phase amphibians and reptiles in the absence of data for these taxa.

Table 9. Summary of the Most Sensitive Endpoints from Terrestrial Toxicity Studies for the amide 

and ester forms of NAA

Taxonomic 

Group

Study Type Surrogate 

Species

Chemical 

(form)

Toxicity Value Acute Toxicity 

Classification 

(MRID) 

Birds1

Acute oral Data Gap

Sub-acute 

dietary

Bobwhite quail, 

Colinus 

virginianus

NAA ethyl ester 

(TGAI)

8-d LC50

>5,620 mg 

ai/kg-diet

Practically nontoxic 

(42584202, 

acceptable)

NAA amide

(TGAI)

8-d LC50

>5,620 mg 

ai/kg-diet

Practically nontoxic 

(42584201, 

acceptable)

Chronic Bobwhite quail

or Mallard duck Data gap

Mammals

Acute Oral

Laboratory rat 

(Rattus 

norvegicus)

NAA ethyl ester 

(TGAI)

LD50 = 2,186 

mg ai/kg-bw

Slightly toxic 

(43494101, 

acceptable)

NAA amide 

(TGAI)

LD50 > 5,000 

mg ai/kg-bw

Practically nontoxic 

(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 incident 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 in 

this database are also in the EIIS. 

EIIS returned a single incident (IO25475-001) with sodium -1-napthalene acetate7involving 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 involved in 

this incident.

7. Exposure Pathways of Concern

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

napthalene acetic acid, its sodium, ammonium, and potassium salts, and the amide indicate that 

direct spray, 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 

application 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 application 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 anionic 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 ethyl 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 one 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 concern 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 

assessments of Napthalene acetic acid and related compounds will incorporate 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 in 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 exposure 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 latest 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 state 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, 2007c), 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 provide insight into the direct and 

indirect effects of pesticides on biotic communities from loss of species that are sensitive to the 

chemicals and from changes in structure and functional characteristics 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 issuing 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

Physical and Chemical Properties: Dissociation Constants for NAA Derivatives: 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 environmental conditions (at pH 7), the ethyl ester and the acetamide 

do not dissociate.

Tables 10a and 10b identify 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 10a. 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 00129382 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 t1/2 = 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 soils). No 

data were submitted on dissociation of 

the acid derivatives; 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 one additional 

study is requested for one of the salts.

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 acetic acid 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 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 KOW.

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 DT50’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 the acid, conducted in three soils, and submitted 

to the EU. According to the EU Draft Assessment Report, naphthalene acetic acid’s Kd values range from 0.40-2.72 

cm3/g, KOCs range from 68.5-138 cm3/gOC, KF values range from 0.297-1.77 cm3/g, and KFOCs range from 50.3-88.5 

cm3/gOC. Should it comply with Agency guidance, this study could be submitted to the Agency. If it is found to be 

acceptable or supplemental, it may be used in the Preliminary Risk Assessment.

Table 10. Submitted Environmental Fate Data for Napthalene acetamide

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 00129382 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 derivative 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 

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 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 

acetamide, 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 chronic 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) for 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 Aquatic Ecological Effects Data for Napthalene acetic acid, Napthalene 

acetamide, and its salts. 

OCSPP

Guideline

Data 

Requirement

Submitted Studies 

(MRID)

Study 

Classification

Data needed 

for Risk 

assessment?

Comments -

assumptions

850.1010 Freshwater 

invertebrate 

acute toxicity

00082526-DM1

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 

Classification

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, 

see Note 2.

850.1300 Freshwater 

invertebrate 

life cycle 

No data submitted Yes 3 Amide form of NAA, 

see 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 of action (e.g.,

Quinclorac and Quinmerac)

3Chronic 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 relatively 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 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 

(aminopyralid, 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.

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 of 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 of toxicity data that can be used to assess the 

effect of naphthaleneacetamide on terrestrial plants is recommended. 

Table 10. Submitted Terrestrial Ecological Effects Data for Napthalene acetic acid and its 

derivatives

OCSPP 

Guideline

Data 

Requirement

Submitted 

Studies (MRID)

Study 

Classification

Data needed 

for Risk 

Assessment?

Comments

850.2100 Avian oral 

toxicity

00065839 w 

MAL1 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

850.2200 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 

Classification

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 758

and Oomen et 

al. 19929

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 

Classification

Data needed 

for Risk 

Assessment?

Comments

850.4100 Seedling 

Emergence 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 KSalt 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 Vegetative Vigor 43141101 with 

K+ salt 

formulation

Yes Yes

(amide form of 

NAA)

Tier 2 with KSalt 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: Physical and Chemical Properties: Dissociation Constants for Naphthalene 

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 derivative compounds.

Guideline Number: 850.3020 

Study Title: Honey bee Acute Contact 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 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 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.
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 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 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 concern.

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-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 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 

adjacent 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 indicated to be at hazardous levels of concern for non-target aquatic 

plants.

Guideline Number: 850.1035: 850.1055

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 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.
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 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 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.

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 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, part 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. Parameters 

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 Barcode: 

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 

Ertman 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 Concentrate 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 Proposed 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-Naphthaleneacetic 

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 (NAA), 

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 Effects 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), Potassium 1-naphthaleneacetate (056003), Ammonium 1-

naphthaleneacetate (056004), Sodium 1-naphthaleneacetate (056007), and Ethyl 1-

naphthaleneacetate (056008)). Memorandum from Carl Chen et al. (Biological and 

Economic Analysis Division) to Christina Scheltema (Pesticide 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.; Beavers, J.B.; Grimes, J.; et al. (1979) Final Report: Acute Oral LDI50--Mallard 

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 Agricultural 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; submitted by Union Carbide Agricultural Products 

Co., Ambler, Pa.; CDL:099029-J)

00042756 Morrissey, A.E. (1979) The Acute Toxicity of 72-A112 to the Rainbow Trout, Salmo 

gairdneri Richardson: UCES Project No. 11506-24-10. (Unpublished study received Sep 

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 72-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 study received Sep 19, 1979 under 264-336; prepared by 

Wildlife International, 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 LCI50--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: Eight-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. (1981) Acute Toxicity of Naphthaleneacetic 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 Products 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, submitted 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 19, 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 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-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 Toxicity 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. 

Unpublished 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 prepared 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 Survey, 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 prepared 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 

Evaluation-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 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 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 Toxicity 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 Acid 

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 (arranged by 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 

Products 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 

Agricultural 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 Agricultural 

Experiment Station, submitted by Interregional Research Project No. 4, New Brunswick, 

N.J.; CDL:090859-B) 

163-1 Leaching/adsorption/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 

Exposure, 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 Labs, 

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 detoxication--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 biochemical 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, naphthomethyl 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 Acetic 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 (NH4-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 B1. Output file from CATABOL v.4.55

Trans Level Quantity P_obtain P_stable Log KOW 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 B2. Naphthalene acetic acid and its Potential Metabolites10

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 : NAPHTHALENEACETIC 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 deg 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 aromatic) | 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 entered)

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 (measured)
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 : Earthworm 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 is 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 predicted 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 DESCRIPTION | 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 | 11 Car-Car | | 2.9019

FRAGMENT | 1 CO-O | | 0.0714

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

RESULT | BOND ESTIMATION METHOD for 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 available

 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 (from 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 | Aliphatic 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 Probability) | | 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 | Aromatic-H | 0.1201 | 0.8410

MolWt| * | Molecular Weight Parameter | | -5.3757

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

 RESULT |Biowin6 (MITI Non-Linear Biodeg Probability)| | 0.2691

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

A Probability Greater Than or Equal to 0.5 indicates --> Readily Degradable

A Probability Less Than 0.5 indicates --> NOT Readily Degradable

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

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

Ready 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 Biowin5 (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 biodegradation 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 ... Structure 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 : 0.00662 

 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-sec

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-LIFE = 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 Acetylenes 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 significantly 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 : NAPHTHALENEACETIC 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 : 000086-87-3

 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 = 20.12 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: NAPHTHALENEACETIC 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 rate 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 10000.00

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 )

 Advection 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-

Naphthaleneacetamide

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 / Potassium 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 TREATMENTs) 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, Honeysuckle, 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 Date 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)

Approved 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