Metrafenone (Ref: BAS 560F)

Metrafenone (Ref: BAS 560F)	Last updated: 22/08/2024
(Also known as: AC 375839)

SUMMARY

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 Moderate alert: Birds chronic ecotoxicity: Moderate; Fish acute ecotoxicity: Moderate; Fish chronic ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Daphnia chronic ecotoxicity: Moderate; Earthworms acute ecotoxicity: Moderate; Earthworms chronic ecotoxicity: Moderate	Human health Moderate alert: Mammals chronic toxicity: Moderate; Reproduction/development effects

GENERAL INFORMATION

Description

A fungicide used to control disease on cereals and other crops

Example pests controlled

Powdery mildew; Eyespot; Ear blight; Rusts

Example applications

Wheat; Barley; Oats; Rye; Triticale; Grapes

Efficacy & activity

Wheat/Eyespot=Moderate; Wheat/Mildew=High; Wheat/Septoria tritici/Low; Mildew=Moderate for protection, Low for eradication

Availability status

Current

Introduction & key dates

2006, introduced

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

30/04/2029

GB LERAP status

Check label - may vary with formulation

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Latvia/Slovakia

Date EC 1107/2009 inclusion expires

15/12/2024

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

Morocco

Chemical structure

Isomerism

None

Chemical formula

C₁₉H₂₁BrO₅

Canonical SMILES

CC1=CC(=C(C(=C1C(=O)C2=C(C=CC(=C2C)Br)OC)OC)OC)OC

Isomeric SMILES

International Chemical Identifier key (InChIKey)

AMSPWOYQQAWRRM-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C19H21BrO5/c1-10-9-14(23-4)18(24-5)19(25-6)15(10)17(21)16-11(2)12(20)7-8-13(16)22-3/h7-9H,1-6H3

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide

Substance groups

Benzophenone compound; Organobromide compound; Aryl phenyl ketone compound

Minimum active substance purity

980 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Protective and curative action. Interferes with hyphal morphogenesis.

CAS RN

220899-03-6

EC number

606-928-8

CIPAC number

752

US EPA chemical code

000325

PubChem CID

6451057

CLP index number

No data found

Molecular mass

409.27

PIN (Preferred Identification Name)

IUPAC name

3'-bromo-2,3,4,6'-tetramethoxy-2',6-dimethylbenzophenone

CAS name

(3-bromo-6-methoxy-2-methylphenyl)(2,3,4-trimethoxy-6-methylphenyl)methanone

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Class (HRAC MoA class)

Not applicable

Herbicide Resistance Class (WSSA MoA class)

Not applicable

Insecticide Resistance Class (IRAC MoA class)

Not applicable

Fungicide Resistance Class (FRAC MOA class)

Examples of recorded resistance

Physical state

White crystalline solid

Formulations

Property

Value

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

BASF

Example products using this active

Attenzo
Flexity
Capalo

Formulation and application details

Often supplied as a suspension concentrate that is mixed with water and used as a spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.492

Low

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

403000

Acetone

1950000

Dichloromethane

261000

Ethyl acetate

363

Toluene

Melting point (°C)

99.2

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

310

Flashpoint (°C)

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

2.00 X 10⁰⁴

Calculated

Log P

4.3

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies

Density (g ml⁻¹)

1.45

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

0.153

Low volatility. If applied directly to plants, drift is a concern & mitigation is advisable

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

1.32 X 10^-01

Moderately volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

206nm = 42443

Surface tension (mN m⁻¹)

67.4

at 20°C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

200.9

Persistent

DT₅₀ (lab at 20 °C)

200.9

Persistent

DT₅₀ (field)

Moderately persistent

DT₉₀ (lab at 20 °C)

912

Very persistent

DT₉₀ (field)

55000

DT₅₀ modelling endpoint

Note

EU 2018 dossier Lab studies DT₅₀ (normalised) range 180.4-252.1 days, 4 soils, DT₉₀ (actual) range 784-1141 days, Soils=4; Field data for silt soil.

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

2.5

Note

Literature study: grapevine leaves

Aqueous photolysis DT₅₀ (days) at pH 7

Value

6.2

Moderately fast

Note

DT₅₀ for test conditions for autumn sunlight 40 deg N

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

Value

Stable

Note

Stable pH 5 to pH 9, 50 °C, 5 days

Water-sediment DT₅₀ (days)

9.3

Fast

Water phase only DT₅₀ (days)

3.9

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)

231

Non-mobile

K_oc (mL g⁻¹)

7061

Notes and range

EU dossier K_d range 48.5-865 mL g⁻¹, K_oc range 2771-18602 mL g⁻¹, Soils=5

Freundlich

K_f (mL g⁻¹)

55.5

Slightly mobile

K_foc (mL g⁻¹)

3105

¹/_n

0.91

Notes and range

EU dossier kf range 24.1-258, K_foc range 1592-5556 mL g⁻¹, ¹/_n range 0.85-0.95, Soils=5

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.91

Calculated

Low leachability

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

Value

1.79 X 10^-02

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

0.63

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)

530

Threshold for concern

CT₅₀ (days)

0.53

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

(3-bromo-6-methoxy-2methylphenyl)(3-hydroxy-2,4-dimethoxy-6-methylphenyl)-methanone (Ref: CL 377160)

Minor fraction

Anaerobic; Photolysis

(3-hydroxy-6-methoxy-2-methylphenyl)(2,3,4-trimethoxy-6-methylphenyl)-methanone (Ref: CL 4084564)

Minor fraction

0.073

(3-bromo-6-methoxy-2-methylphenyl)(4-hydroxy-2,3-dimethoxy-6-methylphenyl)-methanone (Ref: CL 4342231)

Minor fraction

Anaerobic

3-bromo-6-methoxy-2-methyl-benzoic acid (Ref: CL 375816)

Minor fraction

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

7-bromo-4-methoxy-3-(2,3,4-trimethoxy-6-methylphenyl)-1(3H)-isobenzofuranone (Ref: CL 3000402)

Plant

2-(3-bromo-6-methoxy-2-methylbenzoyl)-3,4,5-trimethoxy-benzaldehyde (Ref: CL 379395)

Plant

3-methoxy-2-(2,3,4-trimethoxy-6-methylbenzoyl)-benzaldehyde (Ref: CL 1500836)

Plant

(3-bromo-6-methoxy-2-methylphenyl)[3-(beta-D-glucopyranuronosyloxy)-2,4-dimethoxy-6-methylphenyl]-methanone (Ref: CL 1500698)

Animal

Mono-O-glucuronide of (3-bromo-6-methoxy-2-methylphenyl)(3,4-dihydroxy-2-methoxy-6-methylphenyl)-methanone (Ref: CL 1023363)

Animal

4,5,6-trimethoxy-3-(3-bromo-6-methoxy-2-methylphenyl)-1(3H)-isobenzofuranone (Ref: CL 1023424)

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)

Rat

High

(ppm diet)

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

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2025

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

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

114.7

Anas platyrhynchos

Moderate

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

> 500

Eisenia foetida corr

Moderate

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

50.89

Eisenia foetida corr

Moderate

Soil micro-organisms

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

Dose: 2 mg kg⁻¹ soil

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

37.5

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)

> 114

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

> 291

Apis mellifera

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) as % Mortality at dose 300 g ha⁻¹

Chrysoperla carnea Larva

Beneficial insects (Parasitic wasps) as Mortality LR₅₀ g ha⁻¹ 48 hr

> 300

Aphidius rhopalosiphi Adult

Beneficial insects (Predatory mites) as Mortality LR₅₀ g ha⁻¹ 7 day

> 300

Typhlodromus pyri Protonymph

Beneficial insects (Ground beetles) as % Mortality at dose 300 g ha⁻¹

Poecilus cupreus

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

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

> 0.82

Oncorhynchus mykiss

Moderate

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

0.228

Pimephales promelas

Moderate

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

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

> 0.92

Daphnia magna

Moderate

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

0.225

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)

2.0

Chironomus riparius

Moderate

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

296

Chironomus riparius

Low

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

0.327

Lemna gibba

Moderate

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

0.71

Raphidocelis subcapitata

Moderate

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

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves – Acute EC₅₀ development (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)

> 5000

Rat

Low

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

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.0

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.25

Rat SF=100

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

None allocated

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

None allocated

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

0.43

Rat 90 day SF=100

Dermal penetration studies (%)

2.0-20.0

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

No unacceptable risks to bystanders identified

Occupational

No unacceptable risks to operators or other workers identified utilising PPE/PPC

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

0.1

EU Dir 89/778/EC limit; Calc MAC=750 µg l⁻¹

Mammalian dose elimination route and rate

Extensively metabolised and eliminated mainly via faeces, 85-90% within 72hr

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

Liver & kidney toxicant
US EPA - some evidence to suggest possible human carcinogen

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Environment: H400, H410

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

metrafenone

French

metrafenone

German

Metrafenone

Danish

metrafenon

Italian

metrafenone

Spanish

metrafenona

Greek

Polish

metrafenon

Swedish

metrafenon

Hungarian

Dutch

metrafenon

Norwegian

Record last updated:	22/08/2024
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