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metamitron (Ref: BAY DRW 1139)
** metamitrone ** methiamitron ** BAY 134028 ** 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 metamitron

Description: A herbicide effective against grass and broad-leaved weeds in beet crops

Example pests controlled: Grasses; Broad-leaved weeds

Example applications: Sugarbeet; Fodder beet; Mangels; Red beet

Efficacy & activity: -

Availability status: Current

Introduction & key dates: 1975, first reported

EC Regulation 1107/2009 (repealing 91/414):
Status Approved
Dossier rapporteur/co-rapporteur Denmark/Latvia
Date inclusion expires 31/08/2022
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 -
Chemical formula C10H10N4O
Canonical SMILES CC1=NN=C(C(=O)N1N)C2=CC=CC=C2
Isomeric SMILES No data
International Chemical Identifier key (InChIKey) VHCNQEUWZYOAEV-UHFFFAOYSA-N
International Chemical Identifier (InChI) InChI=1S/C10H10N4O/c1-7-12-13-9(10(15)14(7)11)8-5-3-2-4-6-8/h2-6H,11H2,1H3
2D structure diagram/image available? Yes

Click to access the Cambridge Crystallographic Data Centre (CCDC) website
Cambridge Crystallographic Data Centre diagrams:
Common Name Relationship Link
Metamitron - Click here for the CCDC structure diagram

General status: Click here for further information on the general chemical status information used on this site
Pesticide type Herbicide
Substance group Triazinone
Minimum active substance purity 980 g/kg
Known relevant impurities EU dossier - None declared
Substance origin Synthetic
Mode of action Selective, systemic, absorbed mainly by roots and translocated. Inhibits photosynthesis (photosystem II).
CAS RN 41394-05-2
EC number 255-349-3
CIPAC number 381
US EPA chemical code -
PubChem CID 38854
Molecular mass (g mol-1) 202.21
PIN (Preferred Identification Name) -
IUPAC name 4-amino-4,5-dihydro-3-methyl-6-phenyl-1,2,4-triazin-5-one
CAS name 4-amino-3-methyl-6-phenyl-1,2,4-triazin-5(4H)-one
Other status information -
Relevant Environmental Water Quality Standards -
Herbicide Resistance Classification (HRAC) C1
Herbicide Resistance Classification (WSSA) 5
Insecticide Resistance Classification (IRAC) Not applicable
Fungicide Resistance Classification (FRAC) Not applicable
Examples of recorded resistance -
Physical state Yellow crystals
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
  • Bayer CropScience
  • Makhteshim-Agan
  • Nufarm
  • Sipcam
  • White Agrochemicals
Example products using this active
  • Galahad
  • Goldbeet
  • Goltix 90
  • Goltix Flowable
  • Goltix Super
  • Goltix WG
  • Marquise
  • MM70
  • Skater
UK LERAP status None
Formulation and application details Available in a variety of formulations including wettable powders and water-dispersible granules.


ENVIRONMENTAL FATE

for metamitron

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) 1770 A5 High
Solubility - In organic solvents at 20oC (mg l-1) 37000 A5 - Acetone -
2000 A5 - Xylene -
20000 A5 - Ethyl acetate -
33000 A5 - Dichloromethane -
Melting point (oC) 166.6 A5 -
Boiling point (oC) - - -
Degradation point (oC) 250 A5 -
Flashpoint (oC) Not expected to self ignite; Not highly flammable A5 -
Octanol-water partition coefficient at pH 7, 20oC P 7.08 X 1000 Calculated -
Log P 0.85 A5 Low
Bulk density (g ml-1)/Specific gravity 1.35 L3 -
Dissociation constant (pKa) at 25oC Not applicable A5 -
Note: No dissociation
Vapour pressure at 20oC (mPa) 7.44 X 10-04 A5 Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) 8.95 X 10-08 A5 Non-volatile
GUS leaching potential index Click here for a note on the limitations of the GUS index 2.64 Calculated Transition state
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 4.86 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 Low
Maximum UV-vis absorption L mol-1 cm-1 311.1nm = 11789 A5 -
Surface tension (mN m-1) 68.0 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) 30 K4 Moderately persistent
DT50 (lab at 20oC) 19 A5 Non-persistent
DT50 (field) 11.1 A5 Non-persistent
DT90 (lab at 20oC) 49.8 A5 -
DT90 (field) 36.8 A5 -
DT50 modelling endpoint - - -
Note EU dossier lab studies DT50 range 2.2-44.5 days, DT90 range 11.3-113.6 days, field studies DT50 range 6.6-22.0 days, DT90 range 22.0-73.0 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 0.02 A5 Fast
Note 1.45 hrs river, pH 7 and test conditions, 0.5 hrs pure water, natural summer light, 50 deg N
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 Value 480 A5 Very persistent
Note pH sensitive: DT50 353.2 days at pH 5, 8.5 days at pH 9, all at 20 degC
Water-sediment DT50 (days) 11.1 A5 Fast
Water phase only DT50 (days) 10.5 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 0.89 A5 Moderately mobile
Koc 77.7
Notes and range EU dossier Kd range 0.193-1.59, Koc range 22.9-132.5, Soils=4
Freundlich Kf 1.09 A5 Moderately mobile
Kfoc 86.4
1/n 0.81
Notes and range EU dossier Kf range 0.36-5.88 mL/g, Kfoc range 22.4-303 mL/g, 1.n range 0.67-0.95, Soils=17
pH sensitivity No

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 1107/2009 relevancy Click here for further information on 1107/2009 relevancy
desamino-metamitron This metabolite may cause environmental pollution, click here for further information Soil   0.171   Major fraction, Relevant

Other known metabolites:
Metabolite name and reference Aliases Formation medium / Rate Estimated maximum occurrence fraction Metabolising enzymes
4-amino-6-(4-hydroxyphenyl)-3-methyl-1,2,4-triazin-5(4H)-one metamitron-4-hydroxy Rat - -
6-(4-hydroxyphenyl)-3-methyl-1,2,4-triazin-5(4H)-one metamitron-4-hydroxy-desamino Rat (Urinary, Faeces); Animal - -
3-methyl-4-amino-6-phenyl-1,2,4-triazine-5-one-oxide - Rat (Urinary) - -
5-(carboxymethyl)-2-methylpyrido[2,1-f][1,2,4]triazin-9-ium-4-olate metamitron-triazinium acetic acid Rat (Urinary, Faeces) - -
6-(3-hydroxyphenyl)-3-methyl-1,2,4-triazin-5(4H)-one metamitron-3-hydroxy-desamino Rat (Urinary, Faeces) - -
N-beta-D-glucosyl-4-amino-3-methyl-6-phenyl-1,2,4-triazin-5(4H)-one metamitron-N-glucoside Plant - -
(2Z)-(hydroxyimino)(phenyl)ethanoic acid oxime-acid Plant - -
3-methyl-6-phenyl-1,2,4,5-tetrazine - Water/sediment - -
2-methyl-5-phenyl-1,3,4-oxadiazole - Water/sediment - -
N'-acetylbenzohydrazide N-acetylbenzoic acid hydrazide unknown - -


ECOTOXICOLOGY

for metamitron

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) 75 Q2 Estimated Low potential
CT50 (days) Not available -
Mammals - Acute oral LD50 (mg kg-1) 1183 A5 Rat Moderate
Mammals - Short term dietary NOEL (mg kg-1) > 56 L2 Rat, 2 year High
(ppm diet) > 250 -
Birds - Acute LD50 (mg kg-1) 1302 A5 Coturnix japonica Moderate
Birds - Short term dietary (LC50/LD50) > 904 mg kg bw-1 day-1 A5 Colinus virginianus -
Fish - Acute 96 hour LC50 (mg l-1) >= 190 A5 Oncorhynchus mykiss Low
Fish - Chronic 21 day NOEC (mg l-1) 7.0 A5 Oncorhynchus mykiss Moderate
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) 5.7 A5 Daphnia magna Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 10 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) - - -
Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1) - - -
Aquatic plants - Acute 7 day EC50, biomass (mg l-1) 0.4 A5 Lemna minor Moderate
Non-target plants 54.9 A5 Rape
Seedling emergence, ER50
as g/ha
-
- - -
Algae - Acute 72 hour EC50, growth (mg l-1) 0.4 A5 Pseudokirchneriella subcapitata Moderate
Algae - Chronic 96 hour NOEC, growth (mg l-1) 0.1 Q2 Unknown species Moderate
Honeybees (Apis spp.) Contact acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) > 100 A5 Apis mellifera Low
Oral acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1) > 97.2 A5 Apis mellifera Moderate
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) - - -
-
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) 914 A5 Eisenia foetida Moderate
Earthworms - Chronic NOEC, reproduction (mg kg-1) 28.0 A5 Eisenia foetida Moderate
Other soil macro-organisms Acute LC50 (mg kg-1) - - -
Chronic NOEC (mg kg-1) 100 A5 Folsomia candida -
Other arthropod (1) LR50 g ha-1 14383 >=
A5 Typhlodromus pyri
-
% Effect - - -
Other arthropod (2) LR50 g ha-1 14383 >=
A5 Aphidius rhopalosiphi
-
% Effect - - -
Soil micro-organisms Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect
A5
Dose: 19.5 mg kg-1 soil, 28days
-
Mesocosm study data NOEAEC mg l-1 1.12 A5 Aquatic community -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for metamitron

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) 1183 A5 Rat Moderate
Mammals - Dermal LD50 (mg kg-1 body weight) > 5000 A5 Rat -
Mammals - Inhalation LC50 (mg l-1) 3.17 A5 Rat, 4 hr (nose only) -
Other Mammal toxicity endpoints - -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.03 A5 Dog, SF=100 -
ARfD - Acute Reference Dose (mg kg-1bw day-1) 0.1 A5 Rat, SF=100 -
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) - - -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) 0.036 A5 Dog, SF=100 -
Dermal penetration studies (%) 1.0-20.0 A5 concentration dependent -
Dangerous Substances Directive 76/464 - - -
Exposure Routes Public Acceptable risk to bystanders for proposed uses
Occupational Acceptable risk to operators and other workers wearing PPE
European MRLs Click here for the EU MRL pesticide database
Drinking Water Standards - - -
Drinking Water MAC (μg l-1) - - -

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

A3; B3; C3; D3; E0

-

Respiratory tract irritant Skin irritant Skin sensitiser Eye irritant Phototoxicant

-

-

General human health issues Harmful by inhalation and ingestion
Key: Genotoxicity
A: Chromosome aberration (EFSA database)
B: DNA damage/repair (EFSA database)
C: Gene mutation (EFSA database)
D: Genome mutation (EFSA database)
E: Unspecified genotoxicity type (miscellaneous data source)
0: No data
1: Positive
2: Mixed/ambiguous results
3: Negative
Key: Other
: 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 Prevent generation of dust
Not explosive or oxidising
IMDG Transport Code is usually 9
CLP classification 2013 Health: H302
Environment: H400
EC Risk Classification Click here to view information omn the EU risk phrases Xn - Harmful: R22
N - Dangerous for the environment: R50
EC Safety Classification Click here to view information omn the EU safety phrases S2, S61
WHO Classification II - Moderately hazardous
UN Number Variable with product, usually 3077 or 3082
Waste disposal & packaging Click here for a description of UN packaging marks Packaging Group III (minor danger)


TRANSLATIONS

for metamitron

Language Name
English metamitron
French metamitrone
German Metamitron
Danish metamitron
Italian metamitron
Spanish metamitrona
Greek metamitron
Slovenian metamitron
Polish metamitron
Swedish metamitron
Hungarian metamitron
Dutch metamitron

Record last updated: Friday 08 November 2019
Contact: aeru@herts.ac.uk