2-naphthyloxyacetic acid

2-naphthyloxyacetic acid	Last updated: 24/02/2024
(Also known as: NOA; BNOA; Beta-NOA; 2-NOA; Beta-naphthyloxyacetic acid)

SUMMARY

2-naphthyloxyacetic acid is a plant hormone used to encourage fruit set. It is moderately soluble in water and is not volatile. It is not considered to be environmentally persistent but does have potential to leach to groundwater. It has a moderate to low toxicity to most biodiversity. 2-naphthyloxyacetic acid has a moderate oral mammalian toxicity and is a recognised irritant.

Data alerts

The following alerts are based on the data in the tables below. An absence of an alert does not imply the substance has no implications for human health, biodiversity or the environment but just that we do not have the data to form a judgement.

Environmental fate	Ecotoxicity	Human health
Environmental fate High alert: GUS: High leachability; Drainflow: Mobile	Ecotoxicity Moderate alert: Fish acute ecotoxicity: Moderate; Fish chronic ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Daphnia chronic ecotoxicity: Moderate	Human health Moderate alert: Mammals acute toxicity: Moderate; Reproduction/development effects Warning: Significant data are missing

GENERAL INFORMATION

Description

Used as plant hormone to promote the growth of roots, to encourage fruit set and to prevent fruit from falling prematurely

Example pests controlled

Growth processes; Fruit setting

Example applications

Fruit including apples, pears, plums, cherries

Efficacy & activity

Availability status

Current

Introduction & key dates

circa 1940, introduced

GB regulatory status

GB COPR regulatory status

Not approved

Date COPR inclusion expires

Not applicable

GB LERAP status

No UK approval for use as a pesticide

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

France

Date EC 1107/2009 inclusion expires

Not applicable

EU Candidate for substitution (CfS)

Not applicable

Listed in EU database

Yes

Approved for use (✓) under EC 1107/2009 in the following EU Member States

ATAustria	BEBelgium	BGBulgaria	CYCyprus	CZCzech Republic	DEGermany	DKDenmark	EEEstonia	ELGreece

ESSpain	FIFinland	FRFrance	HRCroatia	HUHungary	IEIreland	ITItaly	LTLithuania	LULuxembourg

LVLatvia	MTMalta	NLNetherlands	PLPoland	PTPortugal	RORomania	SESweden	SISlovenia	SKSlovakia

Approved for use (✓) under EC 1107/2009 by Mutual Recognition of Authorisation and/or national regulations in the following EEA countries

ISIceland	NONorway

Additional information

Also used in

Chemical structure

Isomerism

None

Chemical formula

C₁₂H₁₀O₃

Canonical SMILES

c1ccc2cc(ccc2c1)OCC(=O)O

Isomeric SMILES

International Chemical Identifier key (InChIKey)

RZCJYMOBWVJQGV-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C12H10O3/c13-12(14)8-15-11-6-5-9-3-1-2-4-10(9)7-11/h1-7H,8H2,(H,13,14)

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
2-naphthyloxyacetic acid	-

General status

Pesticide type

Plant Growth Regulator, Herbicide

Substance groups

Auxin PGR; Naphthalene compound

Minimum active substance purity

995 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Absorbed by leaves and roots

CAS RN

120-23-0

EC number

204-380-0

CIPAC number

664

US EPA chemical code

055601

PubChem CID

8422

CLP index number

No data found

Molecular mass

202.21

PIN (Preferred Identification Name)

IUPAC name

2-naphthoxyacetic acid

CAS name

(2-naphthyloxy)acetic acid

Other status information

Chemical subject to PIC regulations; May leach to groundwater.

Relevant Environmental Water Quality Standards

Herbicide Resistance Class (HRAC MoA class)

Not applicable

Herbicide Resistance Class (WSSA MoA class)

Not applicable

Insecticide Resistance Class (IRAC MoA class)

Not applicable

Fungicide Resistance Class (FRAC MOA class)

Not applicable

Examples of recorded resistance

Physical state

White crystalline solid

Related substances & organisms

gibberellic acid

1-naphthylacetic acid

Formulations

Property

Value

Example manufacturers & suppliers of products using this active now or historically

Synchemicals Ltd
Unicrop

Example products using this active

Alligante 36c

Formulation and application details

Usually supplied as a liquid concentrate

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

Solubility - In water at 20 °C (mg l⁻¹)

203

at pH >3

Moderate

Solubility - In organic solvents at 20 °C (mg l⁻¹)

6.1

n-Hexane

790

Toluene

140

Methanol

160000

Acetone

Melting point (°C)

155

Boiling point (°C)

363.5

Degradation point (°C)

No decomposition

Flashpoint (°C)

Octanol-water partition coefficient at pH 7, 20 °C

3.16 X 10⁰²

Calculated

Log P

2.50

Low

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

Dissociation constant pKa) at 25 °C

3.55

Weak acid

Vapour pressure at 20 °C (mPa)

2.89 X 10^-03

Low volatility

Henry's law constant at 25 °C (Pa m³ mol⁻¹)

1.06 X 10^-04

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

Maximum UV-vis absorption L mol⁻¹ cm⁻¹

227nm = 40560-48600

Surface tension (mN m⁻¹)

54.4

100mg l⁻¹

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

3.5

Non-persistent

DT₅₀ (lab at 20 °C)

53.4

Moderately persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

195

Persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier DT₅₀ lab studies range 18.1-100.5 days, DT₉₀ range 10-443 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

Note

Aqueous photolysis DT₅₀ (days) at pH 7

Value

0.37

Fast

Note

0.86 days sunlight at 40degN

Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7

Value

Note

Water-sediment DT₅₀ (days)

53.3

Moderately fast

Water phase only DT₅₀ (days)

28.9

Slow

Sediment phase only DT₅₀ (days)

Air degradation

As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below.

Decay in stored produce DT₅₀

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

1.12

Mobile

K_oc (mL g⁻¹)

72.0

Notes and range

EU dossier K_d range 0.33-2.43 mL g⁻¹, K_oc range 37.5-113.0 mL g⁻¹, Soils=4

Freundlich

K_f (mL g⁻¹)

1.03

Mobile

K_foc (mL g⁻¹)

65.0

¹/_n

0.78

Notes and range

EU dossier K_f range 0.287-2.37, kfoc range 32.6-1100 mL g⁻¹, ¹/_n range 0.74-0.83, Soils=4

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

3.78

Calculated

High leachability

SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate

Value

8.40 X 10^-01

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Mobile

Calculated

Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk

Bio-concentration factor

BCF (l kg⁻¹)

Low risk

Based on LogP < 3

Low risk

CT₅₀ (days)

Known soil and groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

[(6-hydroxy-2-naphthyl)oxy]acetic acid

Rat (Urine)

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

1417

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Coturnix japonica

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

> 1000

as product (4.5% a.s.)

Low

Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)

Soil micro-organisms

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

50.5

Carrot
Vegetative vigour, ER₅₀
as g product ha⁻¹ (Product Conc 4.5% a.s.)

117.8

Carrot
Seeling emergence, ER₅₀
as g product ha⁻¹ (Product Conc 4.5% a.s.)

Honeybees (Apis spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

> 200

Low

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Chronic

Notes

Bumblebees (Bombus spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Mason bees (Osmia spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Other bee species (1)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Other bee species (2)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Beneficial insects (Ladybirds)

Beneficial insects (Lacewings)

Beneficial insects (Parasitic wasps) as Mortality LR₅₀ g ha⁻¹

> 2.27

Aphidius rhopalosiphi

Beneficial insects (Predatory mites) as Mortality LR₅₀ g ha⁻¹

> 2.27

Typhlodromus pyri

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

2.39

Oncorhynchus mykiss

Moderate

Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)

Oncorhynchus mykiss

Moderate

Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

Temperate Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

> 4.52

Daphnia magna

Moderate

Temperate Freshwater Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)

6.7

Daphnia magna

Moderate

Tropical Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)

Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)

Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)

Aquatic plants - Acute 7 day EC₅₀, biomass (mg l⁻¹)

0.19

Lemna gibba

Moderate

Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)

Desmodesmus subspicatus

Low

Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves

HUMAN HEALTH AND PROTECTION

General

Property

Value

Source; quality score; and other information

Interpretation

Threshold of Toxicological Concern (Cramer Class)

High (class III)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

1417

Rat

Moderate

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

4.87

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)

0.01

Rat SF=1000

ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)

0.6

Rat SF=100

AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)

0.03

Rat SF=300

Dermal penetration studies (%)

3.52-10.54

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Acceptable for approved use

Occupational

Acceptable for approved use

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Mammalian dose elimination route and rate

Around 80% excreted in the urine

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

No data found

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

No data found

General human health issues

May cause convulsions, coma, ecephalopathy and kernicterus
Kidney & liver toxicant

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H302, H315, H319, H335

WHO Classification

II (Moderately hazardous)

UN Number

Not regulated

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

2-naphthyloxyacetic acid

French

acide naphthyloxyacetique

German

Danish

Italian

Spanish

Greek

Polish

Swedish

Hungarian

Dutch

Norwegian

Record last updated:	24/02/2024
Contact:	aeru@herts.ac.uk
Please cite as:	Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242