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metrafenone (Ref: BAS 560F)
** AC 375839 ** Translations

Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home

GENERAL INFORMATION Click here for an explantaion of the general chemical status information
for metrafenone

Description: A fungicide used to control disease on cereals

Example pests controlled: Powdery mildew; Eyespot; Ear blight; Rusts

Example applications: Wheat; Barley; Oats; Rye; Triticale

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

EC Regulation 1107/2009 (repealing 91/414):
Status Approved
Dossier rapporteur/co-rapporteur Latvia/Slovakia
Date inclusion expires 30/04/2019
EU Candidate for substitution (CfS) No
Listed in EU database Yes

Approved for use () or known to be used () in the following European countries: Click to access a note on the approvals information on this site

AT

BE

BG

CY

CZ

DE

DK

EE

EL

ES

FI

FR

HR

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

Chemical structure: Click here for further information on the general chemical status information used on this site
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 No data
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
Structure diagram/image available? Yes

General status: Click here for further information on the general chemical status information used on this site
Pesticide type Fungicide
Substance group Benzophenone
Minimum active substance purity 940 g/kg
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 -
CIPAC number 752
US EPA chemical code 000325
PubChem CID 6451057
Molecular mass (g mol-1) 409.3
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 Classification (HRAC) Not applicable
Herbicide Resistance Classification (WSSA) Not applicable
Insecticide Resistance Classification (IRAC) Not applicable
Fungicide Resistance Classification (FRAC) U8
Examples of recorded resistance -
Physical state White crystalline solid
Related substances & organisms

Formulations:
Property Click here for information on the general product and branding information used on this site Value
Example manufacturers & suppliers of products using this active now or historically
  • BASF
Example products using this active
  • Attenzo
  • Flexity
  • Capalo
UK LERAP status None
Formulation and application details Often supplied as a suspension concentrate that is mixed with water and used as a spray.


ENVIRONMENTAL FATE

for metrafenone

Property Click here for information on the parameters used to describe environmental fate on this site Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with fate data Interpretation Click here for information on the way in which we interpret environmental fate data
Solubility - In water at 20oC (mg l-1) 0.492 A5 Low
Solubility - In organic solvents at 20oC (mg l-1) 403000 A5 - Acetone -
1950000 A5 - Dichloromethane -
261000 A5 - Ethyl acetate -
363 A5 - Toluene -
Melting point (oC) 100 A5 -
Boiling point (oC) Decomposes before boiling A5 -
Degradation point (oC) 310 A5 -
Flashpoint (oC) Not expected to self ignite; Not highly flammable A5 -
Octanol-water partition coefficient at pH 7, 20oC P 2.00 X 1004 Calculated -
Log P 4.3 A5 High
Bulk density (g ml-1)/Specific gravity 1.45 A5 -
Dissociation constant (pKa) at 25oC Not applicable A5 -
Note: No dissociation
Vapour pressure at 20oC (mPa) 0.153 A5 Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) 1.32 X 10-01 A5 Moderately volatile
GUS leaching potential index Click here for a note on the limitations of the GUS index 1.22 Calculated Low leachability
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate Click here for a note on the limitations of the SCI-GROW index Value 2.81 X 10-02 Calculated -
Note -
Potential for particle bound transport index Click here for a note on the limitations of the potential for particle bound transport index - Calculated High
Maximum UV-vis absorption L mol-1 cm-1 206nm = 42443 A5 -
Surface tension (mN m-1) 67.4 A5 at 20oC -

Degradation:
Property Click here for information on the parameters used to describe substance degradation Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with degradation data Interpretation Click here for information on the way in which we interpret substance degradation data
General biodegradability -
Soil degradation (days) (aerobic) DT50 (typical) 250.6 A5 Persistent
DT50 (lab at 20oC) 250.6 A5 Persistent
DT50 (field) 146 A5 Persistent
DT90 (lab at 20oC) 909 A5 -
DT90 (field) 734 A5 -
DT50 modelling endpoint - - -
Note EU dossier Lab studies DT50 range 182-365 days, 5 soils, DT90 range 606-1212 days, field study DT50 range 70-221 days European soils
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 6.2 A5 Moderately fast
Note DT50 for test conditions for autumn sunlight 40 deg N
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 Value Stable A5 -
Note Stable pH 5 to pH 9, 50 degC, 5 days
Water-sediment DT50 (days) 9.3 A5 Fast
Water phase only DT50 (days) 3.9 A5 Moderately fast

Soil adsorption and mobility:
Property Click here for information on the parameters used to describe substance adsorption and mobility Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with adsorption and mobility data Interpretation Click here for information on the way in which we interpret substance adsorption and mobility
Linear Kd 231 A5 Non-mobile
Koc 7061
Notes and range EU dossier Kd range 48.5-865 mL/g, Koc range 2771-18602 mL/g, Soils=5
Freundlich Kf 55.5 A5 Slightly mobile
Kfoc 3105
1/n 0.91
Notes and range EU dossier kf range 24.1-258, Kfoc range 1592-5556 mL/g, 1/n range 0.85-0.95, Soils=5
pH sensitivity No

Other known metabolites:
Metabolite name and reference Aliases Formation medium / Rate Estimated maximum occurrence fraction Metabolising enzymes
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) - -
(3-bromo-6-methoxy-2-methylphenyl)[3-(beta-D-glucopyranuronosyloxy)-2,4-dimethoxy-6-methylphenyl]-methanone
(Ref: CL 1500698)
- Animal - -
3-methoxy-2-(2,3,4-trimethoxy-6-methylbenzoyl)-benzaldehyde
(Ref: CL 1500836)
- Plant - -
7-bromo-4-methoxy-3-(2,3,4-trimethoxy-6-methylphenyl)-1(3H)-isobenzofuranone
(Ref: CL 3000402)
- Plant - -
3-bromo-6-methoxy-2-methyl-benzoic acid
(Ref: CL 375816)
- Soil (Anaerobic) - -
(3-bromo-6-methoxy-2methylphenyl)(3-hydroxy-2,4-dimethoxy-6-methylphenyl)-methanone
(Ref: CL 377160)
- Soil (a = Anaerobic, b = Photolysis) a=0.053; b=0.189 -
2-(3-bromo-6-methoxy-2-methylbenzoyl)-3,4,5-trimethoxy-benzaldehyde
(Ref: CL 379395)
- Plant - -
(3-hydroxy-6-methoxy-2-methylphenyl)(2,3,4-trimethoxy-6-methylphenyl)-methanone
(Ref: CL 4084564)
- Soil (Anaerobic) 0.073 -
(3-bromo-6-methoxy-2-methylphenyl)(4-hydroxy-2,3-dimethoxy-6-methylphenyl)-methanone
(Ref: CL 4342231)
- Soil (Anaerobic) - -


ECOTOXICOLOGY

for metrafenone

Property Click here for information on the parameters used to describe substance ecotoxicology Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with ecotoxicology data Interpretation Click here for information on the way in which we interpret substance ecotoxicology
Bio-concentration factor BCF (l kg-1) 530 A5 Threshold for concern
CT50 (days) 0.53 -
Mammals - Acute oral LD50 (mg kg-1) > 5000 A5 Rat Low
Mammals - Short term dietary NOEL (mg kg-1) 43 A5 Rat High
(ppm diet) - -
Birds - Acute LD50 (mg kg-1) > 2025 A5 Colinus virginianus Low
Birds - Short term dietary (LC50/LD50) - - -
Fish - Acute 96 hour LC50 (mg l-1) > 0.82 A5 Oncorhynchus mykiss Moderate
Fish - Chronic 21 day NOEC (mg l-1) - - -
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) > 0.92 A5 Daphnia magna Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 0.225 A5 Daphnia magna Moderate
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) 1.0 A4 Chironomus riparius, 40 day Moderate
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1) - - -
Aquatic plants - Acute 7 day EC50, biomass (mg l-1) - - -
Non-target plants - - -
- - -
Algae - Acute 72 hour EC50, growth (mg l-1) 0.71 A5 Raphidocelis subcapitata Moderate
Algae - Chronic 96 hour NOEC, growth (mg l-1) - - -
Honeybees Contact acute 48 hour LD50 (μg bee-1) > 100 A5 Low
Oral acute 48 hour LD50 (μg bee-1) > 114 A5 Low
Unknown mode acute 48 hour LD50 (μg bee-1) - - -
Earthworms - Acute 14 day LC50 (mg kg-1) > 500 A5 Eisenia foetida, corr Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) 3.0 A5 Eisenia foetida, corr Moderate
Other soil macro-organisms - e.g. Collembola LR50 / EC50 / NOEC / % Effect - - -
Other arthropod (1) LR50 g ha-1 300 48 hour
A5 Aphidius rhopalosiphi, adult
-
% Effect - - -
Other arthropod (2) LR50 g ha-1 500 7 day
A5 Typhlodromus pyri, protonymph
-
% Effect - - -
Soil micro-organisms Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect
A5
Dose: 2 mg kg-1 soil
-
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for metrafenone

General:
Property Click here for information on the parameters used to describe human health and protection issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with human health and protection data Interpretation Click here for information on the way in which we interpret human health and protection data
Threshold of Toxicological Concern (Cramer Class) Click here for a note on the limitations of the Cramer class High (class III) - -
Mammals - Acute oral LD50 (mg kg-1) > 5000 A5 Rat Low
Mammals - Dermal LD50 (mg kg-1 body weight) > 5000 A5 Rat -
Mammals - Inhalation LC50 (mg l-1) > 5.0 A5 Rat -
Other Mammal toxicity endpoints - -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.25 A5 Rat, SF=100 -
ARfD - Acute Reference Dose (mg kg-1bw day-1) None allocated A5 -
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) - - -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) 0.43 A5 Rat, 90 day, SF=100 -
Dermal penetration studies (%) 2.0-20.0 A5 concentration dependent -
Dangerous Substances Directive 76/464 - - -
Exposure Limits - - -
Exposure Routes Public No unacceptable risks to bystanders identified
Occupational No unacceptable risks to operators or other workers identified utilising PPE/PPC
European MRLs Click here for the EU MRL pesticide database
Drinking Water Standards - - -
Drinking Water MAC (μg l-1) 0.1 EU Dir 89/778/EC limit; Calc MAC=750 μg l-1; A5 -

Health issues:
Carcinogen Mutagen Endocrine disrupter Reproduction / development effects Cholinesterase inhibitor Neurotoxicant

-

-

Respiratory tract irritant Skin irritant Skin sensitiser Eye irritant Phototoxicant

-

-

General human health issues Liver toxicant
USEPA - some evidence to suggest possible human carcinogen

: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data found

Handling issues:
Property Click here for information on the parameters used to describe substance handling issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with data on handling issues Interpretation Click here for information on the way in which we interpret data on handling issues
General Click here for a description of the International Maritime Dangerous Goods (IMDG) codes Not explosive
CLP classification 2013 Health: H319, H351, H361fd
Environment: H412
EC Risk Classification Click here to view information omn the EU risk phrases N - Dangerous for the environment: R50, R53
EC Safety Classification Click here to view information omn the EU safety phrases S2, S13, S20/21, S60
WHO Classification NL - Not listed
US EPA Classification (formulation) - -
UN Number -
Waste disposal & packaging Click here for a description of UN packaging marks -


TRANSLATIONS

for metrafenone

Language Name
English metrafenone
French metrafenone
German Metrafenone
Danish metrafenon
Italian metrafenone
Spanish metrafenona
Greek -
Slovenian metrafenon
Polish metrafenon
Swedish metrafenon
Hungarian -
Dutch metrafenon

Record last updated: Thursday 13 September 2018
Contact: aeru@herts.ac.uk
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