Acifluorfen-sodium (Ref: RH 6201 )

Acifluorfen-sodium (Ref: RH 6201 )	Last updated: 24/07/2024
(Also known as: acifluorfene)

SUMMARY

Acifluorfen-sodium is a herbicide that is used to control annual broad-leaved weeds. It is highly soluble in water and in many organic solvents. It is volatile. It may leach to groundwater under certain conditions. It is moderately persistence in soil systems and can be very persistent in aquatic systems. It has a moderate mammalian toxicity and there is some concern regarding its potential for bioaccumulation. It is a recognised irritant. Acifluorfen-sodium is moderately toxic to birds, honeybees and most aquatic organisms. It is relatively non-toxic to earthworms.

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: Persistent; GUS: High leachability	Ecotoxicity Moderate alert: Birds acute ecotoxicity: Moderate; Fish acute ecotoxicity: Moderate; Fish chronic ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Bees acute contact ecotoxicity: Moderate	Human health Moderate alert: Mammals acute toxicity: Moderate; Possible Carcinogen; Reproduction/development effects

GENERAL INFORMATION

Description

A nitrophenyl ether herbicide used for the pre-emergence control of annual broad-leaved weeds

Example pests controlled

Buckwheat; Carpetweed; Cocklebur; Lady's thumb; Morning glory; Moonflower; Nighshade; Pigweed; Waterhelp; Foxtails

Example applications

Soybeans; Peanuts; Beans and peas: Rice

Efficacy & activity

Availability status

Current

Introduction & key dates

1980, first introduced USA

GB regulatory status

GB COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

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

Not applicable

Date EC 1107/2009 inclusion expires

Expired

EU Candidate for substitution (CfS)

Not applicable

Listed in EU database

Yes (as the acid)

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

Australia, USA

Chemical structure

Isomerism

None

Chemical formula

C₁₄H₆ClF₃NNaO₅

Canonical SMILES

C1=CC(=C(C=C1C(F)(F)F)Cl)OC2=CC(=C(C=C2)[N+](=O)[O-])C(=O)[O-].[Na+]

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

RVULBHWZFCBODE-UHFFFAOYSA-M

International Chemical Identifier (InChI)

InChI=1S/C14H7ClF3NO5.Na/c15-10-5-7(14(16,17)18)1-4-12(10)24-8-2-3-11(19(22)23)9(6-8)13(20)21;/h1-6H,(H,20,21);/q;+1/p-1

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
acifluorfen	Parent

General status

Pesticide type

Herbicide

Substance groups

Nitrophenyl ether herbicide

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Selective contact action being absorbed by foliage and roots. Inhibition of protoporphyrinogen oxidase (PPO) - cell membrane disruption

CAS RN

62476-59-9

EC number

263-560-7

CIPAC number

497

US EPA chemical code

114402

PubChem CID

44072

CLP index number

604-041-00-0

Molecular mass

383.6

PIN (Preferred Identification Name)

sodium 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate

IUPAC name

sodium 5-(2-chloro-α,α,α-trifluoro-p-tolyloxy)-2-nitrobenzoate

CAS name

sodium 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate

Other status information

Chemical subject to PIC regulations; PAN Bad Actor

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

Amaranthus rudis, Euphorbia heterophylla

Physical state

Creamy-white to brown solid

Related substances & organisms

acifluorfen

acifluorfen-methyl

fluoroglycofen

lactofen

Formulations

Property

Value

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

Rohm and Haas
United Phosphorus
Rhone-Poulenc

Example products using this active

Blazer
Status
Tackle 2AS
Andover Herbicide

Formulation and application details

Usually supplied as a soluble concentrate but also available as ready-to-use formulations. Often used in conjunction with an adjuvant.

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

620700

High

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

53700

Octanol

641500

Methanol

0.5

Hexane

Melting point (°C)

276

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

274

Flashpoint (°C)

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

1.58 X 10⁰¹

Calculated

Log P

1.2

Low

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.55

Dissociation constant pKa) at 25 °C

3.86

Weak acid

Vapour pressure at 20 °C (mPa)

0.01

Low volatility

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

6.18 X 10^-09

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

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)

154

Persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

Literature data DT₅₀ range 108 days (silt) - 200 days (clay loam); Other sources: DT₅₀ 14.0 days (DW3)

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

Stable

Note

Stable for more than 2 yrs in water

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

Value

Stable

Note

Stable for more than 2 yrs in water

Water-sediment DT₅₀ (days)

Water 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)

K_oc (mL g⁻¹)

Notes and range

Freundlich

K_f (mL g⁻¹)

5.22

Moderately mobile

K_foc (mL g⁻¹)

364

¹/_n

0.92

Notes and range

Mean of several mineral soils; Literature range 44-684 mL kg⁻¹

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

3.15

Calculated

High leachability

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

Value

4.07 X 10^-01

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

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

Bio-concentration factor

BCF (l kg⁻¹)

279

Threshold for concern

CT₅₀ (days)

Not available

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

acifluorfen (Ref: RH 5781)

Major fraction

Known groundwater metabolites

None

Other known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

1540

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)

325

Colinus virginianus

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

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

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

1800

Eisenia foetida

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

Honeybees (Apis spp.)

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

100

Moderate

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

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)

Beneficial insects (Predatory mites)

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)

Oncorhynchus mykiss

Moderate

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

< 1.5

Pimephales promelas 35 day

Moderate

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

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

Daphnia magna

Moderate

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

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

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

2.8

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)

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

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

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

260

Raphidocelis subcapitata

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)

1540

Rat

Moderate

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

2000

Rabbit

Mammals - Inhalation LC₅₀ (mg l⁻¹)

6.91

Rat 4 hr

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

Low risk to Europeans as no longer approved for use

Occupational

Occupational exposure may occur through inhalation and dermal contact

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

May causes irreversible eye damage
Liver toxicant
US EPA - likely to be a human carcinogen at high doses; US Toxics Release Inventory (TRI) Program listed carcinogen

Handling issues

Property

Value and interpretation

General

Corrosive
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H302, H315, H318
Environment: H400, H410

WHO Classification

III (Slightly hazardous)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

acifluorfen-sodium

French

acifluorfene sodium

German

Acifluorfen

Danish

acifluorfen

Italian

acifluorfen

Spanish

acifluorfen sodico

Greek

Polish

acifluorfen sodowy

Swedish

Hungarian

Dutch

Norwegian

Record last updated:	24/07/2024
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