Ethalfluralin (Ref: EL 161)

Ethalfluralin (Ref: EL 161)	Last updated: 23/08/2024
(Also known as: ethalfluraline; HSDB 6474)

SUMMARY

Ethalfluralin is a pre-plant soil applied herbicide. It has a low aqueous solubility and is highly volatile. It may be moderately persistent in some soil systems but is not expected to be persistent in water systems. Based on its physico-chemical properties it is not expected to leach to groundwater. Its toxicity to biodiversity tends to be classed as moderate. The exceptions to this is that it is highly toxic to algae but has a low avian toxicity. Ethalfluralin has a low oral mammalian toxicity and is a skin sensitiser.

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: Potential for particle bound transport: High	Ecotoxicity High alert: Fish chronic ecotoxicity: High	Human health Moderate alert: Possible Carcinogen

GENERAL INFORMATION

Description

A pe-plant soil-applied herbicide used to control most germinating annual grasses and broad-leaved weeds

Example pests controlled

Volunteer grains; Barnyard grass; Crab grass; Carpetweed; Chickweed; Foxtail; Nightshade; Pigweed; Shattercane; Russian thistle

Example applications

Soybeans; Curcubits; Dry beans; Sunflowers; Potatoes; Canola; Peanuts; Lentils; Cotton; Melon, Hemp

Efficacy & activity

Availability status

Voluntarily withdrawn

Introduction & key dates

1971, first synthesised; circa 1975, first registered Turkey; 1983, first registered USA

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

Greece

Date EC 1107/2009 inclusion expires

Not applicable

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

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

Chemical structure

Isomerism

None

Chemical formula

C₁₃H₁₄F₃N₃O₄

Canonical SMILES

CCN(CC(=C)C)C1=C(C=C(C=C1[N+](=O)[O-])C(F)(F)F)[N+](=O)[O-]

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

PTFJIKYUEPWBMS-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C13H14F3N3O4/c1-4-17(7-8(2)3)12-10(18(20)21)5-9(13(14,15)16)6-11(12)19(22)23/h5-6H,2,4,7H2,1,3H3

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide

Substance groups

Dinitroaniline herbicide

Minimum active substance purity

950 g kg⁻¹

Known relevant impurities

EU dossier - nitrosamines

Substance origin

Synthetic

Mode of action

Selective. Microtube inhibitor - reducing seedling root growth.

CAS RN

55283-68-6

EC number

259-564-3

CIPAC number

516

US EPA chemical code

113101

PubChem CID

41381

CLP index number

No data found

Molecular mass

333.3

PIN (Preferred Identification Name)

IUPAC name

N-ethyl-α,α,α-trifluoro-N-(2-methylallyl)-2,6-dinitro-p-toluidine

CAS name

N-ethyl-N-(2-methyl-2-propenyl)-2,6-dinitro-4-(trifluoromethyl)benzenamine

Other status information

Chemical subject to PIC regulations; Risk of drift

Relevant Environmental Water Quality Standards

Herbicide Resistance Class (HRAC MoA class)

Herbicide Resistance Class (WSSA MoA class)

Insecticide Resistance Class (IRAC MoA class)

Not applicable

Fungicide Resistance Class (FRAC MOA class)

Not applicable

Examples of recorded resistance

Lolium rigidum

Physical state

Yellow to orange coloured crystals

Formulations

Property

Value

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

Hillfield Trading Cyprus
Dow AgroSciences
Loveland Products
Elanco

Example products using this active

Gilan
Sonalan
Curbit
Sonalen
Edge

Formulation and application details

Usually supplied as an emulsifiable concentrate

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.01

Low

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

1000000

Acetone

130000

n-Hexane

124000

Methanol

1000000

Dichloromethane

Melting point (°C)

55.5

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

256

Flashpoint (°C)

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

1.29 X 10⁰⁵

Calculated

Log P

5.11

High

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

Highly volatile. If applied directly to plants or soil, drift is a concern & mitigation is advisable

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

18.0

Moderately volatile

Volatilisation as max % of applied dose lost

From plant surface

48 hr

From soil surface

3.2

48 hr

Volatilisation is not considered critical for air pollution

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

Neutral solution: 269nm = 8110, 377nm = 2330
Acidic solution: 269nm = 8060, 377nm = 2360
Basic solution: 269nm = 7860, 377nm = 2360

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Moderately persistent

DT₅₀ (lab at 20 °C)

39.8

Moderately persistent

DT₅₀ (field)

Moderately persistent

DT₉₀ (lab at 20 °C)

107

Persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 20-70 days, DT₉₀ range 80-155 days, field study DT₅₀ range 21-104 days; Other sources: 60 days (DW4)

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

0.3

Fast

Note

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

Value

Stable

Note

Not pH sensitive: DT₅₀ > 1 year pH 3 to pH 9 at 20 °C

Water-sediment DT₅₀ (days)

13.5

Fast

Water phase only DT₅₀ (days)

10.5

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)

55.8

Non-mobile

K_oc (mL g⁻¹)

6364

Notes and range

EU dossier K_d range 15.6-95.9 mL g⁻¹, K_oc range 5200-7992 mL g⁻¹, Soils=4

Freundlich

K_f (mL g⁻¹)

48.6

Non-mobile

K_foc (mL g⁻¹)

5356

¹/_n

0.964

Notes and range

EU dossier K_d range 11.9-97.0, K_foc range 3967-8083 mL g⁻¹, ¹/_n range 0.954-0.984, Soils=4

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.47

Calculated

Low leachability

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

Value

9.71 X 10^-03

Calculated

Note

Potential for particle bound transport index

High

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

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

1.8

Calculated using the Atkinson method

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

1330

Whole fish

Threshold for concern

CT₅₀ (days)

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

5-trifluoromethyl-3-nitro-1,2-benzendiamene (Ref: LY-50030)

Minor fraction

0.036

Photolysis

2,6-dinitro-4-(trifluoromethyl)benzeneamine (Ref: LY-35836)

Minor fraction

Anaerobic

N-ethyl-N-(2-methyl-2-propenyl)-3-nitro-5-(trilfuoromethyl)-1,2-benzenediamine

Minor fraction

Aerobic

1-ethyl-2-(1-methylethyl)-7-nitro-5-(trifluoromethyl)benzimidazole

Minor fraction

Anaerobic

N-(2-methyl-2-propenyl)-2,6-dinitro-4-trifluoromethyl)benzenamine

Minor fraction

Aerobic

2,3,4,5-tetrahydro-5-ethyl-3-methylene-6-nitro-8-(trifluoromethyl)-1H-1,5-benzodiazepine

Minor fraction

Anaerobic

N-ethyl-2,6-dinitro-4-(trifluoromethyl)benzenamine (Ref: LY-48800)

Minor fraction

Aerobic

2-methyl-7-nitro-5-trifluoromethyl-1H-benzimidazole-3-oxide (Ref: LY-67255)

Minor fraction

0.013

Photolysis

2,6-dinitro-4-(trifluoromethyl)phenol

Minor fraction

0.032

Aerobic

1-hydroxy-2-methyl-4-nitro-6-trifluoro-methyl-1H-benzimidazole (Ref: LY-65138)

Minor fraction

0.040

2-(1-methylethylenyl)-4-nitro-6-trifluoromethyl-1H-benzimidazole (Ref: LY-275166)

Minor fraction

0.043

Known groundwater metabolites

Metabolite

EC SANCO/221/2000 relevancy

ADI (mg kg⁻¹ bodyweight day⁻¹)

WHO drinking water guidance value (μg L⁻¹ day⁻¹)

2-methyl-7-nitro-5-trifluoromethyl-1H-benzimidazole-3-oxide (Ref: LY-67255)

Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

N-ethyl-N-(2-methyl-2-propenyl)-5-(trifluoromethyl)-1,2,3-benzenetriamine

Water (Anaerobic)

2-methyl-6-trifluoromethyl-4-nitro-1H-benzimidazole

Water (Photolysis)

1-hydroxy-2-methyl-4-nitro-6-trifluoro-methyl-1H-benzimidazole

Water (Photolysis)

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

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

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 832 mg kg bw⁻¹ day⁻¹

Colinus virginianus

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

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

> 1000

Eisenia foetida

Low

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

25.3

Eisenia foetida

Moderate

Soil micro-organisms

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

Dose: 6.92 mg kg⁻¹ soil

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)

> 100

Apis mellifera

Low

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

> 109.9

Apis mellifera

Low

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)

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

< 33.4

Aphidius rhopalosiphi

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

> 639

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)

0.136

Oncorhynchus mykiss

Moderate

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

0.0004

Oncorhynchus mykiss 50 day

High

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

3.35

Danio rerio EC₅₀ Embryo

Moderate

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

> 0.13

Daphnia magna

Moderate

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

0.0237

Daphnia magna

Moderate

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

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

0.23

Americamysis bahia

Moderate

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

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

0.3

Chironomus riparius

Moderate

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

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

0.080

Lemna gibba

Moderate

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

0.009

Pseudokirchneriella subcapitata

High

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)

> 5000

Rat

Low

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

2000

Rabbit

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 2.8

Rat

Other Mammal toxicity endpoints

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

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

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 (%)

Dangerous Substances Directive 76/464

List II

Exposure Routes

Public

No unacceptable risks 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

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

No data found

General human health issues

May cause dyspnea, anorexia, nausea and vomiting
US EPA - possible human carcinogen; CLP data - suspected carcingen

Handling issues

Property

Value and interpretation

General

Prevent generation of mists
Not explosive or oxidising
Not explected to auto-ignite, Not highly flammable
IMDG Transport Hazard Class 6.1

CLP classification 2013

Health: H315, H317, H319, H351
Environmernt: H400, H410

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

UN3077

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

ethalfluralin

French

ethalfluraline

German

Ethalfluralin

Danish

ethalfluralin

Italian

etafluralin

Spanish

etafluralina

Greek

Polish

etalfluralina

Swedish

Hungarian

etalfluralin

Dutch

Norwegian

Record last updated:	23/08/2024
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