Flufenacet (Ref: FOE 5043)

Flufenacet (Ref: FOE 5043)	Last updated: 27/01/2021
(Also known as: fluthiamide; fluofenacet ; thiafluamide)

SUMMARY

Flufenacet is an EU approved oxyacetamide herbicide. It is moderately soluble in water, is not highly volatile but may, under certain conditions, be persistent in soil and water/sediment systems. It is moderately toxic to humans via the oral route and is considered to be a skin sensitiser. With the exception of honeybees where the toxicity is low, flufenacet is either moderately or highly toxici to most fauna and flora.

GENERAL INFORMATION

Description

A broad spectrum soil herbicide, often used in conjunction with other herbicides, used, post-emergence, to control grasses and some broad-leaved weeds

Example pests controlled

Certain annual grasses including black-grass, Broad-leaved weeds including velvet leaf, morning glory and common cocklebur

Example applications

Corn; Soybeans; Winter wheat; Winter barley; Potatoes; Sunflowers; Asparagus; Cotton; Chilli; Tobacco

Efficacy & activity

Efficiacy suuported by data derived from field experiments and extensive global use.

Availability status

Current

Introduction & key dates

1998, USA; 2004, EU

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

31/10/2024

UK LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Poland/France

Date EC 1107/2009 inclusion expires

31/10/2021

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

Philippines; US, Canada, Chile, Kenya, China, iIsrael

Chemical structure

Isomerism

Chemical formula

C₁₄H₁₃F₄N₃O₂S

Canonical SMILES

CC(C)N(C1=CC=C(C=C1)F)C(=O)COC2=NN=C(S2)C(F)(F)F

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

IANUJLZYFUDJIH-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C14H13F4N3O2S/c1-8(2)21(10-5-3-9(15)4-6-10)11(22)7-23-13-20-19-12(24-13)14(16,17)18/h3-6,8H,7H2,1-2H3

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide

Substance group

Oxyacetamide

Minimum active substance purity

970 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Selective with meristematic activity. Inhibition of VLCFA (inhibition of cell division).

CAS RN

142459-58-3

EC number

CIPAC number

588

US EPA chemical code

121903

PubChem CID

86429

Molecular mass

363.33

PIN (Preferred Identification Name)

N-(4-fluorophenyl)-N-(propan-2-yl)-2-{[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]oxy}acetamide

IUPAC name

4'-fluoro-N-isopropyl-2-[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yloxy]acetanilide

CAS name

N-(4-fluorophenyl)-N-(1-methylethyl)-2-[[5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl]oxy]acetamide

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Herbicide Resistance Classification (WSSA)

Insecticide Resistance Classification (IRAC)

Not applicable

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Physical state

White to tan coloured, odourless solid

Related substances & organisms

diflufenican

isoxaflutole

metribuzin

pendimethalin

solvent naphtha

Formulations

Property

Value

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

Artist
Cadu Star
Firebird
Shooter
Regatta
Axiom
Herold SC
Fosbury

Example products using this active

Bayer CropScience
BASF
Standon

Formulation and application details

Usually supplied as a suspension concentrate and used as a foliar spray

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)

280000

Acetone

200000

Toluene

8700

Hexane

170000

Propanol

Melting point (°C)

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

150

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

3.16 X 10⁰³

Calculated

Log P

3.5

High

Bulk density (g ml⁻¹)

1.45

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

0.09

Low volatility

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

1.3 X 10^-03

Non-volatile

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

pH 2: 201nm=18131, 235nm=7307
pH 7: 235nm=7106
pH 10: 235nm=7161

Surface tension (mN m⁻¹)

59.4

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

19.7

Non-persistent

DT₅₀ (lab at 20 °C)

19.7

Non-persistent

DT₅₀ (field)

39.0

Moderately persistent

DT₉₀ (lab at 20 °C)

77.5

Moderately persistent

DT₉₀ (field)

132.4

DT₅₀ modelling endpoint

57.6

worse case not normalised.

Note

EU 2017 dossier lab studies DT₅₀ range 7.04-37.4 days, DT₉₀ range 24.4-191.4 days, Soils=10; field studies DT₅₀ range 14.2-68.1 days, DT₉₀ range 53.4-132.4, Soils=16 days

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

Note

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Stable

Note

Not a significant degradation route

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

Value

Stable

Note

Stable pH 5 to pH 9

Water-sediment DT₅₀ (days)

Moderately fast

Water phase only DT₅₀ (days)

Stable

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

Moderately mobile

K_oc

401

Notes and range

Freundlich

K_f

4.38

Moderately mobile

K_foc

273.3

¹/_n

0.92

Notes and range

EU 2017 dossier K_f range 1.48-8.96 mL g⁻¹, kfoc range 161.6-643.5 mL g⁻¹, ¹/_n range 0.848-0.980, Soils=10

pH sensitivity

None

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

2.49

Calculated

Transition state

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

Value

1.45 X 10^-01

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

FOE sulphonic acid (Ref: AE 0841914)

Soil

0.263

Major fraction, Relevant

FOE oxalate (Ref: AE 0841913)

Soil

0.265

Major fraction, Relevant

FOE alcohol (Ref: AND 1403)

Soil

0.212

Major fraction, Relvant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

({2-[(4-fluorophenyl)(isopropyl)amino]-2-oxoethyl}sulfinyl)acetic acid (Ref: AE 0841915)

FOE thioglycolate sulfoxide

Soil; Plants; Water

N-(4-fluorophenyl)-N-isopropyl-2-(methylsulfanyl)acetamide (Ref: BCS-CP38571)

FOE methylsulfide

Water; Animal; Corn

N-(4-fluorophenyl)-N-isopropyl-2-(methylsulfinyl)acetamide

FOE methylsulfoxide

Soil; Water; Plant; Rat

N-(4-fluorophenyl)-N-isopropyl-2-(methylsulfonyl)acetamide (Ref: BCS-CO62475)

FOE methylsulfone

Rat; Plant; Soil; Water

2-chloro-N-(4-fluorophenyl)-N-isopropylacetamide (Ref: BCS-AA70824)

FOE chloroacetanilide

Rat; Plant; Soil

5-(trifluoromethyl)-1,3,4-thiadiazol-2-ol (Ref: BCS-AA41715)

FOE-thiadone

Rat; Plant; Soil; Water

N-acetyl-S-{2-[(4-fluorophenyl)(isopropyl)amino]-2-oxoethyl}cysteine

FOE acetyl cysteine

Animal

N-acetyl-S-{2-[(4-fluorophenyl)amino]-2- oxoethyl}cysteine

FOE des-i-propyl cysteine

Rat

N-acetyl-3-({2-[(4- fluorophenyl)(isopropyl)amino]-2- oxoethyl}sulfinyl)alanine

FOE S-oxo cysteine

Rat

N-(4-fluorophenyl)-N-isopropylacetamide

FOE amine acetate

Animal; Plant

N-(4-fluorophenyl)-2- (methylsulfinyl)acetamide

FOE des-i-propyl methylsulfoxide

Rat

N-(4-fluorophenyl)-2- (methylsulfonyl)acetamide

FOE des-i-propyl methylsulfone

Animal

fluoro-hydroxy-des-i-propyl methylsulfone

Rat

N-acetyl-S-(2-fluoro-5-{[(methylsulfonyl)acetyl]amino}phenyl)cysteine

hydroxy-des-i-propyl methylsulfone

Rat

hydroxy-des-i-propyl methylsulfone-glutaminic acid

Rat

2,2'-disulfanediylbis[N-(4-fluorophenyl)-Nisopropylacetamide]

FOE disulfide

Rat

N-(4-hydroxyphenyl)acetamide

hydroxy-des-i-propyl amine acetate

Rat

2-amino-5-fluorophenol

2-A-5-FP

Rat

gamma-glutamyl-S-{2-[(4- fluorophenyl)(isopropyl)amino]-2- oxoethyl}cysteinylglycine

FOE glutathione

Rat; Animal

S-{2-[(4-fluorophenyl)(isopropyl)amino]-2- oxoethyl}cysteine

FOE cysteine

Rat; Animal; Plant

5-(trifluoromethyl)-1,3,4-thiadiazol-2-yl hexopyranosiduronic acid

thiadone glucuronide

Rat; Animal

3-hexopyranosyl-5-(trifluoromethyl)-2,3- dihydro-1,3,4-thiadiazol-2-one

ThN glucoside

Plant

2,4-dioxo-4-{[5-(trifluoromethyl)-1,3,4- thiadiazol-2-yl]oxy}butanoic acid

Th oxalyl acetic acid

Rat

N-(4-fluorophenyl)acetamide

DIFAAC: BCS-AA22989

Hen

N-(4-fluorophenyl)-N-(1-hydroxypropan-2-yl)- 2-(methylsulfonyl)acetamide

HOIFAMSO2

Rat; Hen

N-(4-hydroxyphenyl)-N-(1-hydroxypropan-2- yl)-2-(methylsulfinyl)acetamide

LMeOH-3

Hen

N-(4-fluorophenyl)-2-hydroxy-N-acetamide

Des-isopropyl-FOE alcohol

Rat

4-fluoro-N-isopropylaniline

4-Fluoro-N-(1- methylethyl)benzamine

Rat

3-({2-[(4-fluorophenyl)(isopropyl)amino]-2- oxoethyl}sulfinyl)-2-hydroxypropanoic acid

FOE sulfinyl lactic acid

Plant

N-(carboxyacetyl)-3-[2-oxo-5-(trifluoromethyl)-1,3,4-thiadiazol-3(2H)-

Th-malonylalanyl conjugate

Soybean

[(4-fluorophenyl)amino](oxo)acetic acid

FOE des-isopropyl oxalate

Plant

[(4-fluoro-3-hydroxyphenyl)amino](oxo)acetic acid

FOE 3-OH-des-isopropyl oxalate

Plant

3-({2-[(4-fluorophenyl)(isopropyl)amino]-2-oxoethyl}sulfinyl)-2-(hexopyranosyloxy)propanoic acid

FOE sulfinyl lactic acid glucoside

Plant

3-({2-[(4-fluorophenyl)(isopropyl)amino]-2- oxoethyl}sulfinyl)-2- (hexopyranosyloxy)propanoic acid

FOE sulfonyl lactic acid

Plant

3-({2-[(4-fluorophenyl)(isopropyl)amino]-2- oxoethyl}sulfinyl)alanine

FOE cysteine sulfoxide

Fish; Plant

3-({2-[(4-fluorophenyl)(isopropyl)amino]-2- oxoethyl}sulfanyl)-2-hydroxypropanoic acid

FOE sulfanyl lactic acid

Plant

3-({2-[(4-fluorophenyl)(isopropyl)amino]-2- oxoethyl}sulfanyl)-2- (hexopyranosyloxy)propanoic acid

FOE sulfanyl lactic acid glucoside

Plant

N-(carboxyacetyl)-S-{2-[(4- fluorophenyl)(isopropyl)amino]-2- oxoethyl}cysteine

FOE malonylcysteine conjugate FAM-MalCys IUPAC: N-(carboxyacetyl)-S-{2-[(4- fluorophenyl)(isopropyl)amino]-2- oxoethyl}cysteine

Corn

N-(4-fluorophenyl)-N-isopropyl-2- sulfanylacetamide

FOE free sulfide

Animal; Corn

2,2,2-trifluoroethanesulfonic acid

FOE 5043- trifluoroethanesulfonic acid

Soil

trifluoroacetic acid

Rat; Plant; Soil

4-fluoro-N-methylethylaniline thiodiacetic acid amide

FOE thioglycolate sulfide

Soil; Water

3-({2-[(4-fluorophenyl)(1-hydroxypropan-2- yl)amino]-2-oxoethyl}sulfinyl)alanine

isopropyl hydroxy cysteine

Fish

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

71.4

Low potential

CT₅₀ (days)

Not available

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

598

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

1.67

Rat

High

(ppm diet)

97.5

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

37.4

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

1608

Colinus virginianus

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

> 4970 ppm

Anas platyrhynchos

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

9.4

Anas platyrhynchos NOEL

High

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

2.13

Lepomis macrochirus

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.2

Oncorhynchus mykiss

Moderate

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

30.9

Daphnia magna

Moderate

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

3.26

Daphnia magna

Moderate

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

1.78

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)

0.002

Lemna gibba

High

Non-target plants

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

0.00204

Raphidocelis subcapitata 72 hour

High

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

Honeybees (Apis spp.)

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

> 109.2

Apis melifera

Low

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

> 100

Apis melifera

Low

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)

> 100

Bombus terrestris

Low

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 pollinators (1)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

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)

219

Eisenia foetida

Moderate

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

> 1.2

Eisenia foetida corr

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

98.43

Folsomia candida 28d

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

Mortality / Fecundity / Parasitism [Dose: 0.06 kg ha⁻¹]
Aphidius rhopalosiphi adult

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

100

Mortality and Reproduction [Dose: 0.06 kg ha⁻¹]
Typhlodromus pyri protonymph

Soil micro-organisms

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

Dose: 4 mg kg⁻¹ soil

Mesocosm study data

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)

598

Rat

Moderate

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 3.74

Rat (nose only)

Other Mammal toxicity endpoints

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

0.005

Rat SF=200

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

0.017

Dog SF=100

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

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

0.017

Dog 90 day SF=100

Dermal penetration studies (%)

0.2-4.7

concentration dependent

Dangerous Substances Directive 76/464

List II

Exposure Routes

Public

Minimal risk from dietary exposure
Risk assessment indicates ARfD would not normally be execeeded

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

Eye irritant

Phototoxicant

General human health issues

Potential liver, spleen and thyroid toxicant

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Code is usually 9

CLP classification 2013

Health: H302, H317, H373
Environment: H400, H410

EC Risk Classification

Xn - Harmful: R22, R43, R48/22
N - Dangerous for the environment: R50, R53

EC Safety Classification

S2, S13, S24, S37, S60, S61

WHO Classification

II (Moderately hazardous)

UN Number

Usually 3077

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

flufenacet

French

flufenacet

German

Flufenacet

Danish

flufenacet

Italian

flufenacet

Spanish

flufenacet

Greek

flufenacet

Polish

flufenacet

Swedish

flufenacet

Hungarian

flufenacet

Dutch

flufenacet

Record last updated:	27/01/2021
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