Etofenprox (Ref: MTI 500)

Etofenprox (Ref: MTI 500)	Last updated: 24/10/2024
(Also known as: ethofenprox; OMS 3002)

SUMMARY

Etofenprox is a pyrethroid broad-spectrum insecticide used to control a range of pests on fruit, vegetables and in paddy fields. It has a low aqueous solubility, a low volatility and is not normally expected to persist in soil or water systems. Risk of leaching to groundwater is low. Etofenprox is highly toxic to bees, fish and aquatic invertebrates, moderately toxic to earthworms and algae. It has a low oral toxicity to humans and no chronic health impacts have been identified. However, there are concerns that it may pose a risk to breast-fed children

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 Moderate alert: Potential for particle bound transport: Medium	Ecotoxicity High alert: Fish acute ecotoxicity: High; Fish chronic ecotoxicity: High; Daphnia acute ecotoxicity: High; Daphnia chronic ecotoxicity: High; Bees acute contact ecotoxicity: High; Bees acute oral ecotoxicity: High	Human health High alert: Reproduction/development effects

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

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

31/12/2028

GB LERAP status

Crop over 5m DRT - See Authorisation for Crop LERAP Details

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

31/03/2027

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
	✓		✓		✓			✓

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

USA, Japan

Chemical structure

Isomerism

None

Chemical formula

C₂₅H₂₈O₃

Canonical SMILES

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

Isomeric SMILES

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

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
etofenprox	-

General status

Pesticide type

Insecticide, Other substance

Other bioactivity & uses

Disinfectant, Wood preservative

Substance groups

Pyrethroid insecticide; Pyrethrid ether insecticide

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

CLP index number

604-091-00-3

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 Class (HRAC MoA class)

Not applicable

Herbicide Resistance Class (WSSA MoA class)

Not applicable

Insecticide Resistance Class (IRAC MoA class)

Fungicide Resistance Class (FRAC MOA class)

Not applicable

Examples of recorded resistance

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

Physical state

White crystals

Formulations

Property

Value

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

Landis
Mitsui Chemicals
ISAGRO
Certis

Example products using this active

Trebon
Punkaso
Boxer

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)

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

7.94 X 10⁰⁶

Calculated

Log P

6.9

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies

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

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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 (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

4.01

Note

Published literature RL₅₀ range 2.09.8 days, 3 field and undercover crops, various matrices, n=4

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

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)

427

Non-mobile

K_oc (mL g⁻¹)

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 (mL g⁻¹)

K_foc (mL g⁻¹)

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

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

Bio-concentration factor

BCF (l kg⁻¹)

CT₅₀ (days)

Known soil metabolites

Metabolite

Major/Minor fraction

$Click here for further information on Major/Minor fraction$

Estimated maximum occurrence fraction

Notes

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

Minor fraction

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

Minor fraction

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

Minor fraction

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

Minor fraction

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

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

alpha-CO-4-OH

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

alpha-CO

Rat; Plant

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

4-hydroxyetofenprox; 4-OH

Animal; Rat (Faeces; Bile); Surface water; Sediment

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

Animal

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

gamma-CO

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

EPMP

Animal

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

OH-PAlcohol

3-phenoxybenzoic acid

m-PB acid; PB acid

Rat (Urine); Animal; Water

3-phenoxybenzyl alcohol

m-PB-alcohol

Rat; Animal

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

4-AcO

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

PENA

Animal; Water

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

desethyletofenprox

3-(4-hydroxyphenoxy)benzoic acid

4-OH-PB acid

Rat (Urine); Animal

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat 1 yr

(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)

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

> 24.6

Moderate

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

Soil micro-organisms

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

Dose: 0.67 kg ha⁻¹

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

Honeybees (Apis spp.)

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

> 0.038

Apis mellifera

High

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

0.366

Apis mellifera

High

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

Chronic

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 bee species (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 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) as Mortality LR₅₀ g ha⁻¹

17.9

Chrysoperla carnea 1st instar

Beneficial insects (Parasitic wasps) as Mortality LR₅₀ g ha⁻¹ 48 hr

0.42

Aphidius rhopalosiphi Adult

Beneficial insects (Predatory mites) as Mortality LR₅₀ g ha⁻¹ 7 day

0.70

Typhlodromus pyri Protonymph

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)

0.0027

Oncorhynchus mykiss

High

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

0.0032

Oncorhynchus mykiss

High

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

> 0.056

Danio rerio

High

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

0.0012

Daphnia magna

High

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

0.000054

Daphnia magna

High

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)

> 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)

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

Mesocosm study data

NOEAEC mg l⁻¹

0.002

Aquatic community

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)

> 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

Great Britain

GB MRL Register

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Mammalian dose elimination route and rate

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
US EPA - possible human carcinogen

Handling issues

Property

Value and interpretation

General

Not explosive
Not explected to auto-ignite, Not highly flammable

CLP classification 2013

Health: H362
Environment: H400, H410

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

etofenprox

French

etofenprox

German

Etofenprox

Danish

etofenprox

Italian

etofenprox

Spanish

etofenprox

Greek

Polish

etofenproks

Swedish

Hungarian

etofenprox

Dutch

Norwegian

Record last updated:	24/10/2024
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