Flurtamone (Ref: RPA 590515)

Flurtamone (Ref: RPA 590515)	Last updated: 24/07/2024
(Also known as: SX 1802; RE 40885)

SUMMARY

Flurtamone is a herbicide used to control broad-leaved weeds and grasses. It has a low aqueous solubility, low volatility and, based on its chemical properties, is not expected to leach to groundwater. It is not normally persistent in soil or water-sediment systems. It has a low mammalian toxicity and no serious health risks have been identified from the literature. It has a low to moderate toxicity to most terrestrial and aquatic species, with the exception of aquatic plants for which toxicity is high.

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: Moderately persistent; GUS: Transition state; Drainflow: Moderately mobile	Ecotoxicity High alert: Birds chronic ecotoxicity: High	Human health Moderate alert: Reproduction/development effects

GENERAL INFORMATION

Description

A pre-emergence or post-emergence herbicide used pre-planting and soil incorporated to control broad-leaved and some grasses

Example pests controlled

Broad-leaved weeds, Grasses

Example applications

Cereals including barley, wheat, oats, rye; Sunflower; Cotton; Peas

Efficacy & activity

Many products using flurtamone have been in use in the EU more many years with efficiacy proven in the field and under test conditions.

Availability status

Current

Introduction & key dates

circa 1990, introduced

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

Czech Republic/Ireland

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

Chemical structure

Isomerism

A chiral molecule existing in the R- and S-forms

Chemical formula

C₁₈H₁₄F₃NO₂

Canonical SMILES

CNC1=C(C(=O)C(O1)C2=CC=CC=C2)C3=CC(=CC=C3)C(F)(F)F

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

NYRMIJKDBAQCHC-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C18H14F3NO2/c1-22-17-14(12-8-5-9-13(10-12)18(19,20)21)15(23)16(24-17)11-6-3-2-4-7-11/h2-10,16,22H,1H3

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
flurtamone	Unstated isomer

General status

Pesticide type

Herbicide

Substance groups

Furan compound; Cyclic ketone compound; Unclassified pesticide

Minimum active substance purity

982 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Bleaching - Carotenoid biosynthesis inhibitor.

CAS RN

96525-23-4

EC number

619-224-0

CIPAC number

569

US EPA chemical code

PubChem CID

91755

CLP index number

606-053-00-1

Molecular mass

333.30

PIN (Preferred Identification Name)

IUPAC name

(RS)-5-methylamino-2-phenyl-4-(α,α,α-trifluoro-m-tolyl)furan-3(2H)-one

CAS name

5-(methylamino)-2-phenyl-4-[3-(trifluoromethyl)phenyl]-3(2H)-furanone

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

Physical state

Pale yellow powder

Formulations

Property

Value

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

Bayer CropScience
Aventis
Rhone-Poulenc

Example products using this active

Bacara
Graduate
Ingot
Chevron
Dolmen

Formulation and application details

Usually supplied as a soluble concentrate applied as an aqueous sloution using standard spraying equipment. at 0.5 L product in 200-400 L water / ha

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

10.7

at pH5

Low

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

350000

Acetone

199000

Methanol

Hexane

133000

Ethyl acetate

Melting point (°C)

148.5

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

190

Flashpoint (°C)

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

1.74 X 10⁰³

Calculated

Log P

3.24

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data based on LogP

Density (g ml⁻¹)

1.38

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

7.0 X 10^-07

Low volatility

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

2.03 X 10^-08

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

24 hr

Volatilisation is not considered critical for air pollution

From soil surface

24 hr

Volatilisation is not considered critical for air pollution

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

Neutral solution: 276.2nm=28128
Acidic solution: 272.6nm=23912
Basic solution: 215.6nm=17530, 272.6nm=18755

Surface tension (mN m⁻¹)

72.1

at 20 °C 99.1%

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Not considered to be readily biodegradable

Soil degradation (days) (aerobic)

DT₅₀ (typical)

10.7

Non-persistent

DT₅₀ (lab at 20 °C)

10.7

Non-persistent

DT₅₀ (field)

35.8

Moderately persistent

DT₉₀ (lab at 20 °C)

250

Persistent

DT₉₀ (field)

184

DT₅₀ modelling endpoint

Note

EU 2017 dossier lab studies DT₅₀ range 9.1-11.7 days, DT₉₀ range 30.2-39.9 days, Soils=4; field studies DT₅₀ range 46-65 days, DT₉₀ range 152-216 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

1.0

Moderately fast

Note

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

Value

Stable

Note

Stable pH 5 to pH 9 at 25 °C

Water-sediment DT₅₀ (days)

82.4

Moderately fast

Water phase only DT₅₀ (days)

16.0

Slow

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)

6.95

Moderately mobile

K_foc (mL g⁻¹)

257.3

¹/_n

0.876

Notes and range

EU 2016 dossier K_f range 4.47-10.62 mL g⁻¹, K_foc range 225-288 mL g⁻¹, ¹/_n range 0.87-0.86, Soils=5

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

2.47

Calculated

Transition state

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

Value

1.40 X 10^-01

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

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

Calculated using the Atkinson method. Assumed 1.5E+06 OH/cm³, 12 hr

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

27.5

Whole fish

Low potential

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

trifluoroethanoic acid

Minor fraction

0.055

3-trifluoromethylbenzoic acid (Ref: RE-54488)

Major fraction

0.247

benzoic acid

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)

trifluoroethanoic acid

Not relevant

Other known metabolites

None

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)

6.3

Rat

High

(ppm diet)

100

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

247

Rat Reproductive NOAEL

Low

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2530

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 6000 mg kg feed⁻¹

Colinus virginianus

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

7.3

Colinus virginianus NOEL

High

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

> 1800

Eisenia foetida

Low

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

47.5

Eisenia foetida corr

Moderate

Soil micro-organisms

Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: <5% slight stimulation of soil respiration

Dose: Not stated

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

500

Folsomia candida corr

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)

> 105.1

Apis mellifera

Low

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

Chronic as 10-day LDD₅₀ µg bee⁻¹ day⁻¹

4.7

Apis mellifera

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 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

> 500

Aphidius rhopalosiphi

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

> 500

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)

6.64

Pimephales promelas

Moderate

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

0.63

Oncorhynchus mykiss

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)

0.071

Daphnia magna

Moderate

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)

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)

0.0141

Lemna gibba

Moderate

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

0.073

Pseudokirchneriella subcapitata

Moderate

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

0.024

Navicula pelliculosa

Moderate

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)

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 2.2

Rat 4 hr (whole body)

Other Mammal toxicity endpoints

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

0.03

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

0.5

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

0.19

Rat SF=300

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

0.05

Dermal penetration studies (%)

0.3-8.0%

concentration dependent

Dangerous Substances Directive 76/464

List II

Exposure Routes

Public

No unacceptable risks for bystanders identified

Occupational

No unacceptable risks to operators or 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

Mainly via faeces (49-61%) and urine (38-43%) mostly within 24hr

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

No data found

; ; ; ;

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

Possible kidney, liver and spleen toxicant

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Hazard Class 9
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Environment: H400, H410

WHO Classification

Not listed (Not listed)

UN Number

UN3077

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

flurtamone

French

flurtamone

German

Flurtamone

Danish

flurtamon

Italian

flurtamone

Spanish

flurtamone

Greek

flurtamone

Polish

flurtamon

Swedish

flurtamon

Hungarian

Dutch

flurtamone

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