Ethoxyquin

Ethoxyquin	Last updated: 23/05/2018
(Also known as: ethoxyquine; polyethoxyquinoline; PEQ)

GENERAL INFORMATION

Description

A fungicide used to control scald and other diseases, post-harvest in top fruit normally used in enclosed areas

Example pests controlled

Scald

Example applications

Top fruit

Efficacy & activity

Availability status

Current

Introduction & key dates

circa 1990

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

UK LERAP status

No UK approval for use

EC Regulation 1107/2009 (repealing 91/414)

EC Directive 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Germany

Date EC 1107/2009 inclusion expires

Expired

EU Candidate for substitution (CfS)

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

Also used in

Chemical structure

Isomerism

Chemical formula

C₁₄H₁₉NO

Canonical SMILES

CCOC1=CC2=C(C=C1)NC(C=C2C)(C)C

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

DECIPOUIJURFOJ-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C14H19NO/c1-5-16-11-6-7-13-12(8-11)10(2)9-14(3,4)15-13/h6-9,15H,5H2,1-4H3

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide, Veterinary substance, Other substance

Other constituent type

Antioxidant

Substance group

Quinoline

Minimum active substance purity

950 g kg⁻¹

Known relevant impurities

EU dossier - p-phenetidine 0.75 g kg⁻¹

Substance origin

Synthetic

Mode of action

Anti-oxidant effecting plant growth

CAS RN

91-53-2

EC number

202-075-7

CIPAC number

517

US EPA chemical code

055501

PubChem CID

3293

Molecular mass

217.34

PIN (Preferred Identification Name)

6-ethoxy-2,2,4-trimethyl-1,2-dihydroquinoline

IUPAC name

1,2-dihydro-2,2,4-trimethylquinolin-6-yl ethyl ether

CAS name

6-ethoxy-1,2-dihydro-2,2,4-trimethylquinoline

Other status information

Chemical subject to PIC regulations; Should not be used on Red Delicious, Golden Delicious or late picked Winesap apples as may reduce quality

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Not applicable

Fungicide Resistance Classification (FRAC)

Not known

Examples of recorded resistance

Physical state

Yellow to brown coloured viscous liquid

Formulations

Property

Value

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

Xedaquine
Nix-Scald
Stop-Scald
Santoquin

Example products using this active

Monsanto
Pennwalt

Formulation and application details

Usually formulated as an emulsifiable concentrate

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

60.0

at 25 °C

Moderate

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

Miscible

n-Heptane

Miscible

Methanol

Miscible

Acetone

Miscible

Ethyl acetate

Melting point (°C)

< -20

Boiling point (°C)

150

Degradation point (°C)

150

Flashpoint (°C)

150

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

2.45 X 10⁰³

Calculated

Log P

3.39

High

Bulk density (g ml⁻¹)

1.03

Dissociation constant pKa) at 25 °C

4.56

@ 22degC

Vapour pressure at 20 °C (mPa)

0.346

at 25 °C

Low volatility

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

4.43 X 10^-02

at 25 °C

Non-volatile

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

Neutral solution: 350nm = 2450, 228nm = 24300
Acidic solution: 299nm = 1680, 259nm = 6450, 224nm = 24600
Basic solution: 350nm = 2460, 228nm = 250000

Surface tension (mN m⁻¹)

58.5

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

DT₅₀ (lab at 20 °C)

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

Note

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Note

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

Value

Note

Water-sediment DT₅₀ (days)

Water phase only DT₅₀ (days)

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

Slightly mobile

K_oc

3208

Notes and range

Estimated

Freundlich

K_f

K_foc

¹/_n

Notes and range

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

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

Value

Cannot be calculated

Note

Potential for particle bound transport index

Potential for loss via drain flow

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

methylethoxyquin

MEQ

Plant

dihydroethoxyquin

DHEQ

Plant

dihydromethylethoxyquin

DHMEQ

Plant

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

Low risk

CT₅₀ (days)

Not available

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

1726

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)

2417

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 1505 mg kg bw⁻¹ day⁻¹

Colinus virginianus

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

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

Daphnia magna

Moderate

Aquatic invertebrates - Chronic 21 day NOEC (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)

Non-target plants

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

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

6.1

Pseudokirchneriella subcapitata

Low

Honeybees (Apis 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)

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

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 pollinators (1)

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

Mode of exposure

Other pollinators (2)

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

Mode of exposure

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

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

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

Soil micro-organisms

Mesocosm study data

NOEAEC mg l⁻¹

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)

1726

Rat

Moderate

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 1.97

Rat 4 hr (whole body)

Other Mammal toxicity endpoints

Intraperitoneal LD₅₀ = 200 mg kg⁻¹

Mouse

Intravenous LD₅₀ = 178 mg kg⁻¹

Mouse

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

0.005

JMPR 2005

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

0.5

JMPR 2005

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

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

Dermal penetration studies (%)

100

default

Dangerous Substances Directive 76/464

Exposure Routes

Public

Occupational

European MRLs

EU MRL pesticide database

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

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

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

May cause dermatitis, probable sensitiser
Possible liver and kidney toxicant

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising

CLP classification 2013

Health: H302

EC Risk Classification

Xn - Harmful: R22

EC Safety Classification

S2, S24

WHO Classification

NL (Not listed)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

ethoxyquin

French

ethoxyquine

German

Ethoxyquin

Danish

ethoxyquin

Italian

etossichina

Spanish

etoxiquina

Greek

Polish

etoksychina

Swedish

Hungarian

etoxiquin

Dutch

ethoxychin

Record last updated:	23/05/2018
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