Fomesafen (Ref: PP 021)

Fomesafen (Ref: PP 021)	Last updated: 06/03/2024
(Also known as: fomesafene; fomesafen acid)

SUMMARY

Fomesafen is a selective herbicide. It is moderately soluble in aqueous solution, is relatively volatile but does have potential to leach to groundwater. It is persistent in soils and aquatic systems. It is moderately toxic to mammals and although a recognised irritant no other significant health issues have been identified. It is not toxic to birds or fish but considered moderately toxic to aquatic crustaceans, honeybees and 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: GUS: High leachability; Drainflow: Mobile	Ecotoxicity Moderate alert: Bees acute oral ecotoxicity: Moderate; Earthworms acute ecotoxicity: Moderate	Human health Moderate alert: Mammals acute toxicity: Moderate; Possible Carcinogen; Reproduction/development effects

GENERAL INFORMATION

Description

A pre-emergence herbicide for use in leguminous crops for post-emergence control of broad-leaved weeds

Example pests controlled

Pigweed, Black nightshade, Velvetleaf, Cocklebur

Example applications

Legumes; Cotton; Soybeans; Potatoes; Tomatoes

Efficacy & activity

Availability status

Unknown

Introduction & key dates

1983, first reported

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

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

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

Chemical structure

Isomerism

None

Chemical formula

C₁₅H₁₀ClF₃N₂O₆S

Canonical SMILES

CS(=O)(=O)NC(=O)C1=C(C=CC(=C1)OC2=C(C=C(C=C2)C(F)(F)F)Cl)[N+](=O)[O-]

Isomeric SMILES

International Chemical Identifier key (InChIKey)

BGZZWXTVIYUUEY-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C15H10ClF3N2O6S/c1-28(25,26)20-14(22)10-7-9(3-4-12(10)21(23)24)27-13-5-2-8(6-11(13)16)15(17,18)19/h2-7H,1H3,(H,20,22)

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide

Substance groups

Organochloride fungicide; Organofluoride fungicide; Amide fungicide; Nitrophenol etther fungicide

Minimum active substance purity

95%

Known relevant impurities

Substance origin

Synthetic

Mode of action

Selective, absorbed by leaves and roots. Inhibits protoporphyrinogen oxidase (PROTOX), leading to irreversible cell membrane damage.

CAS RN

72178-02-0

EC number

276-439-9

CIPAC number

None allocated

US EPA chemical code

123802

PubChem CID

51556

CLP index number

604-040-00-5

Molecular mass

438.76

PIN (Preferred Identification Name)

5-(2-chloro-α,α,α-trifluoro-p-tolyloxy)-N-mesyl-2-nitrobenzamide

IUPAC name

5-(2-chloro-α,α,α-trifluoro-p-tolyloxy)-N-mesyl-2-nitrobenzamide

CAS name

5-[2-chloro-4-(trifluoromethyl)phenoxy]-N-(methylsulfonyl)-2-nitrobenzamide

Other status information

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

White crystalline solid

Related substances & organisms

fomesafen-sodium

Formulations

Property

Value

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

FCC Ltd
King Tech
AgroCare
ICI Plant Protection
BOC Sciences
Syngenta Australia Pty Ltd

Example products using this active

Eagrow
Reflex
Flexstar
Format

Formulation and application details

Usually supplied as an soluble concentrate or liquid concentratate.

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

Moderate

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

300000

Acetone

25000

Methanol

1900

Xylene

10000

Dichloromethane

Melting point (°C)

217

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

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

6.31 X 10^-02

Calculated

Log P

-1.2

Low

Fat solubility of residues

Solubility

Likely to be soluble

Data type

Based on chemical group

Density (g ml⁻¹)

1.574

Dissociation constant pKa) at 25 °C

2.83

Forms water soluble salts, strong acid

Vapour pressure at 20 °C (mPa)

4.00 X 10^-03

Low volatility

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

2.00 X 10^-07

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)

DT₅₀ (field)

Moderately persistent

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

Field studies DT₅₀ range 59-112 days

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

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

Value

Note

Water-sediment DT₅₀ (days)

Fast

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)

Mobile

K_oc (mL g⁻¹)

Notes and range

Literature studies state K_oc range 150-1200 (R3)

Freundlich

K_f (mL g⁻¹)

1.89

Moderately mobile

K_foc (mL g⁻¹)

228

¹/_n

0.77

Notes and range

Literature data: K_f range 1.38-3.02 mL g⁻¹, K_foc range 115-348 mL g⁻¹, ¹/_n range 0.65-0.83, soils=6

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

3.18

Calculated

High leachability

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

Value

4.08 X 10^-01

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Mobile

Calculated

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

Bio-concentration factor

BCF (l kg⁻¹)

Whole fish

Low potential

CT₅₀ (days)

Not available

Known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

1250

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

0.25

Rat

High

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 5000

Anas platyrhynchos

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

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

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

1000

Moderate

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)

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

Moderate

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)

> 170

Oncorhynchus mykiss

Low

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

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

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

> 330

Daphnia magna

Low

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

> 100

Daphnia magna LOEC

Low

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

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

22.1

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)

0.17

Unknown species

Moderate

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)

1250

Rat

Moderate

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

1000

Rabbit

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 4.97

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 I

Exposure Routes

Public

Occupational

Occupational exposure may occur through inhalation of spray mists and aerosols 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

Eye irritant

Phototoxicant

No data found

General human health issues

Probably liver toxicant
US EPA - possible human carcinogen

Handling issues

Property

Value and interpretation

General

No information available

CLP classification 2013

Health: H302

WHO Classification

II (Moderately hazardous)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

Limited shelf life. Store 0-6 DegC

TRANSLATIONS

Language

Name

English

fomesafen

French

fomesafen

German

Fomesafen

Danish

fomesafen

Italian

fomosafen

Spanish

fomesafen

Greek

Polish

fomesafen

Swedish

Hungarian

fomezafen

Dutch

Norwegian

Record last updated:	06/03/2024
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