Etofenprox (Ref: MTI 500)

Etofenprox (Ref: MTI 500)	Last updated: 19/01/2021
(Also known as: ethofenprox; OMS 3002)

GENERAL INFORMATION

Description

An insecticide used to control a range of pests including aphids on fruit, vegetables and in paddy fields.

Example pests controlled

Aphids, Moths, Leaf miners

Example applications

Fruit; Vegetables; Paddy fields

Efficacy & activity

Availability status

Current

Introduction & key dates

1987, introduced Japan

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

31/12/2024

UK LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Slovakia/Italy

Date EC 1107/2009 inclusion expires

31/12/2021

EU Candidate for substitution (CfS)

Yes - two 'Persistent-Bioaccumulative-Toxic' criteria

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

USA, Japan

Chemical structure

Isomerism

Chemical formula

C₂₅H₂₈O₃

Canonical SMILES

CCOC1=CC=C(C=C1)C(C)(C)COCC2=CC(=CC=C2)OC3=CC=CC=C3

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

YREQHYQNNWYQCJ-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C25H28O3/c1-4-27-22-15-13-21(14-16-22)25(2,3)19-26-18-20-9-8-12-24(17-20)28-23-10-6-5-7-11-23/h5-17H,4,18-19H2,1-3H3

2D structure diagram/image available?

Yes

General status

Pesticide type

Insecticide

Substance group

Pyrethroid

Minimum active substance purity

970 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Broad spectrum with contact and stomach action. Sodium channel modulator.

CAS RN

80844-07-1

EC number

407-980-2

CIPAC number

471

US EPA chemical code

128965

PubChem CID

71245

Molecular mass

376.49

PIN (Preferred Identification Name)

1-{[2-(4-ethoxyphenyl)-2-methylpropoxy]methyl}-3-phenoxybenzene

IUPAC name

2-(4-ethoxyphenyl)-2-methylpropyl 3-phenoxybenzyl ether

CAS name

1-((2-(4-ethoxyphenyl)-2-methylpropoxy)methyl)-3-phenoxybenzene

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Anopheles sacharovi, Bemisia tabaci, Culex pipiens molestus, Helicoverpa armigera, Anopheles stephensi, Blattella germanica

Physical state

White crystals

Related substances & organisms

phenthoate

Formulations

Property

Value

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

Trebon
Punkaso
Boxer

Example products using this active

Landis
Mitsui Chemicals
ISAGRO
Certis

Formulation and application details

Often supplied an an emulsifiable concentrate that is mixed with water and used as a spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.0225

Low

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

837000

Ethyl acetate

877000

Acetone

49000

Methanol

856000

Xylene

Melting point (°C)

37.4

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

200

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

7.94 X 10⁰⁶

Calculated

Log P

6.9

High

Bulk density (g ml⁻¹)

1.17

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

8.13 X 10^-04

Low volatility

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

0.0136

Non-volatile

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

Neutral solution: Maxima at 273.6nm
Acidic & Basic solution: Maxima at 273.5nm

Surface tension (mN m⁻¹)

68.12

20.1°C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Non-persistent

DT₅₀ (lab at 20 °C)

Non-persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

Moderately persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 7-25 days, DT₉₀ range 22-84 days

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

2.1

Note

Published literature RL₅₀ range 2.0-2.2 days, 2 field crops, various matrices, n=3

Aqueous photolysis DT₅₀ (days) at pH 7

Value

6.3

Moderately fast

Note

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

Value

Stable

Note

Stable pH 4 to pH 9 up to 50 °C

Water-sediment DT₅₀ (days)

13.3

Fast

Water phase only DT₅₀ (days)

5.7

Moderately fast

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

427

Non-mobile

K_oc

17757

Notes and range

EU dossier K_d range 315-590 mL g⁻¹, K_oc range 13758-23995 mL g⁻¹, n=3

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

-0.30

Calculated

Low leachability

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

Value

5.35 X 10^-03

Calculated

Note

Estimated concentrations of chemicals with Koc values greater than 9995 ml g⁻¹ are beyond the scope of the regression data used in SCI-GROW development. If there are concerns for such chemicals, a higher tier groundwater exposure assessment should be considered, regardless of the concentration returned by SCI-GROW

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

3-(4-hydroxyphenoxy)benzoic acid

4-OH-PB acid

Rat (Urinary); Animal

2-(4-hydroxyphenyl-2-methylpropyl 3-phenoxybenzyl ether

Animal; Soil; Groundwater

2-(ethoxyphenyl)-2-methylpropanoic acid-(4-hydroxyphenoxy)benzyl ester

gamma-CO

unknown

2-(ethoxyphenyl)-2-methylpropyl-3-(4-hydroxyphenoxy)benzoate

alpha-CO-4-OH

unknown

2-(4-ethoxyphenyl)-2-methylpropyl 3-phenoxybenzoate

alpha-CO

Soil; Rat; Plant

2-(4-ethoxyphenyl)-2-methylpropyl 3-(4-hydroxy) phenoxybenzyl ether

4-hydroxyetofenprox; 4-OH

Animal; Rat (Faeces; Bile); Water/sediment; Soil; Groundwater

2-(4-ethoxyphenyl)-2-methylpropyl alcohol

PENA

Animal; Water

3-phenoxybenzyl-2-(4-hydroxyphenyl)-2-methylpropyl ether

desethyletofenprox

unknown

2-(4-ethoxyphenyl)-2-methylpropionic acid

EPMP

Animal

2-(4-hydroxyphenyl-2-(4-ethoxyphenyl)-2-methylpropylether

Soil; groundwater

3-phenoxybenzoic acid

m-PB acid; PB acid

Rat (Urinary); Animal; Water

3-phenoxybenzyl alcohol

m-PB-alcohol

Rat; Animal

2-(4-acetoxyphenyl)-2-methylpropyl-3-phenoxybenzyl ether

4-AcO

unknown

2-(2-hydroxyphenyl)-2-methylpropyl alcohol

OH-PAlcohol

unknown

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

CT₅₀ (days)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat 1 year

(ppm diet)

3.7

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Anas platyrhynchos

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5000 mg kg feed⁻¹

Anas platyrhynchos

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.0027

Oncorhynchus mykiss

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.0032

Oncorhynchus mykiss

High

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

0.0012

Daphnia magna

High

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

0.000054

Daphnia magna

High

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

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

> 0.021

Chironomus riparius

High

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

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

0.0038

Chironomus riparius 10 day

High

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

Non-target plants

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

> 0.15

Pseudokirchneriella subcapitata

Moderate

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

0.15

Pseudokirchneriella subcapitata

Moderate

Honeybees (Apis spp.)

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

> 0.038

High

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

0.366

High

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)

0.177

Osmia bicornis

High

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)

0.051

Megachile rotundata

High

Mode of exposure

Contact

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)

> 24.6

Moderate

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

0.42

48 hour
Aphidius rhopalosiphi adult

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

0.70

7 day
Typhlodromus pyri protonymph

% Effect

Soil micro-organisms

Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect

Dose: 0.67 kg ha⁻¹

Mesocosm study data

NOEAEC mg l⁻¹

0.002

Aquatic community

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)

> 2000

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.88

Rat

Other Mammal toxicity endpoints

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

0.03

Mouse SF=100

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

1.0

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

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

0.06

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

Exposure Routes

Public

No unacceptable risk to bystanders identified

Occupational

No unacceptable risks to operators or other workers identified

MRLs

European

EU MRL pesticide database

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Thyroid toxicant

Handling issues

Property

Value and interpretation

General

Not explosive

CLP classification 2013

Health: H362
Environment: H400, H410

EC Risk Classification

N - Dangerous for the environment: R50, R53

EC Safety Classification

S2, S13, S27/28, S36/37/39

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

etofenprox

French

etofenprox

German

Etofenprox

Danish

etofenprox

Italian

etofenprox

Spanish

etofenprox

Greek

Polish

etofenproks

Swedish

Hungarian

etofenprox

Dutch

Record last updated:	19/01/2021
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