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Prometon (Ref: G 31435)
(Also known as: prometone; 2,4-prometone)
SUMMARY
Prometon is a non-selective herbicide. It is highly soluble in water, volatile and, based on its chemical properties, it is highly mobile and has a high potential to leach to groundwater. It can be highly persistent in both soil and aquatic systems. It has a relatively low mammalian toxicity and is not expected to bioaccumulate. It is classified as an irritant. It is moderately toxic to birds, most aquatic species and honey bees.
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:
Very persistent; GUS: High leachability; Drainflow: Mobile
Ecotoxicity
Moderate alert:
Birds acute ecotoxicity: Moderate; Fish acute ecotoxicity: Moderate; Fish chronic ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Bees acute contact ecotoxicity: Moderate
Human health
Moderate alert:
Mammals acute toxicity: Moderate
Warning:
Significant data are missing
GENERAL INFORMATION
Description
A herbicide for annual and perennial broad-leaved weed, brush and grass control mainly in non-cropping situations.
Example pests controlled
Broad-leaved weeds and grasses including Johsongrass, Bermudagrass, foxtail, crabgrass, docks, goosegrass, nightshade, pigweed
Example applications
Non-cropped areas including paths, around buildings, utility sites
Efficacy & activity
-
Availability status
Current
Introduction & key dates
circa 1962
UK regulatory status
UK COPR regulatory status
Not approved
Date COPR inclusion expires
Not applicable
UK LERAP status
No UK approval for use
EC Regulation 1107/2009 (repealing 91/414)
EC Regulation 1107/2009 status
Not approved
Dossier rapporteur/co-rapporteur
Not applicable
Date EC 1107/2009 inclusion expires
Not applicable
EU Candidate for substitution (CfS)
Not applicable
Listed in EU database
No
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
USA
Chemical structure
Isomerism
None
Chemical formula
C₁₀H₁₉N₅O
Canonical SMILES
CC(C)NC1=NC(=NC(=N1)OC)NC(C)C
Isomeric SMILES
No data
International Chemical Identifier key (InChIKey)
ISEUFVQQFVOBCY-UHFFFAOYSA-N
International Chemical Identifier (InChI)
InChI=1S/C10H19N5O/c1-6(2)11-8-13-9(12-7(3)4)15-10(14-8)16-5/h6-7H,1-5H3,(H2,11,12,13,14,15)
2D structure diagram/image available?
Yes
Cambridge Crystallographic Data Centre diagrams
Common Name Relationship Link
prometon -
General status
Pesticide type
Herbicide
Substance groups
Methoxytriazine herbicide; triazine herbicide
Minimum active substance purity
-
Known relevant impurities
-
Substance origin
Synthetic
Mode of action
Non-selective, systemic absorbed by foliage and roots, inhibits photosynthesis. Affects photosystem II competing with plastoquinone and modifying electron transport processes.
CAS RN
1610-18-0
EC number
216-548-0
CIPAC number
175
US EPA chemical code
080804
PubChem CID
4928
CLP index number
No data found
Molecular mass
225.3
PIN (Preferred Identification Name)
-
IUPAC name
N2,N4-diisopropyl-6-methoxy-1,3,5-triazine-2,4-diamine
CAS name
6-methoxy-N,N'-bis(1-methylethyl)-1,3,5-triazine-2,4-diamine
Other status information
Potential groundwater contaminant
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
White crystalline powder
Formulations
Property
Value
Example manufacturers & suppliers of products using this active now or historically
  • Ciba-Geigy Group
  • Makhteshim Agan
Example products using this active
  • Pramitol
  • Primatol
  • Gesafram
Formulation and application details
Usually formulated as emulsifiable concentrates, wettable powders and pellets. Application of sprays or granules can be before or after weed emergence.
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
620
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
 High
Solubility - In organic solvents at 20 °C (mg l⁻¹)
250000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Benzene		 -
500000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Acetone		 -
500000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Methanol		 -
250000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Toluene		 -
Melting point (°C)
91.5
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
 -
Boiling point (°C)
- - -
Degradation point (°C)
- - -
Flashpoint (°C)
- - -
Octanol-water partition coefficient at pH 7, 20 °C
P
8.13 X 1002 Calculated -
Log P
2.91
K3 K = Research datasets (e.g. Pandora, Demetra; these datasets no longer available). Norman Ecotoxicology database. (click here )
3 = Unverified data of known source
 Moderate
Fat solubility of residues
Solubility
- - -
Data type
- - -
Density (g ml⁻¹)
1.088
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
 -
Dissociation constant pKa) at 25 °C
9.73
DW4 DW = Don Wauchope personal database for Pka data: Wauchope, R. D. and Edwards, J. Dissociation constants for pesticide active ingredients: a database and comparison with predicted values. Dataset is no longer available.
4 = Verified data
 -
Weak acid
Vapour pressure at 20 °C (mPa)
0.306
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 Low volatility
Henry's law constant at 25 °C (Pa m³ mol⁻¹)
4.38 X 10-04
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
 Non-volatile
Maximum UV-vis absorption L mol⁻¹ cm⁻¹
- - -
Surface tension (mN m⁻¹)
- - -
Degradation
Property
Value
Source; quality score; and other information
Interpretation
General biodegradability
-
Soil degradation (days) (aerobic)
DT₅₀ (typical)
500
DW4 DW = Don Wauchope personal database for Pka data: Wauchope, R. D. and Edwards, J. Dissociation constants for pesticide active ingredients: a database and comparison with predicted values. Dataset is no longer available.
4 = Verified data
 Very persistent
DT₅₀ (lab at 20 °C)
932
R3 R = Peer reviewed scientific publications
3 = Unverified data of known source
at 25 °C		 Very persistent
DT₅₀ (field)
- - -
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
DT₅₀ modelling endpoint
- - -
Note
-
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
- - -
Note
-
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7
Value
Stable
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 Stable
Note
General literature states >200 days
Water-sediment DT₅₀ (days)
- - -
Water phase only DT₅₀ (days)
- - -
Soil adsorption and mobility
Property
Value
Source; quality score; and other information
Interpretation
Linear
Kd
0.16
R3 R = Peer reviewed scientific publications
3 = Unverified data of known source
 Mobile
Koc
43.2
Notes and range
Literature data: Kd range 0.15-0.17 mL g⁻¹, koc rnage 34.9-51.5 mL g⁻¹, soils=2; Other sources Log Koc 2.54 at 25 °C (R3)
Freundlich
Kf
0.29
R3 R = Peer reviewed scientific publications
3 = Unverified data of known source
 Moderately mobile
Kfoc
75.2
1/n
0.918
Notes and range
Literature data: Kf range 0.22-0.36 mL g⁻¹, kfoc range 66.7-83.7 mL g⁻¹, 1/n range 0.872-0.963, Soils=2
pH sensitivity
-
Fate indices
Property
Value
Source; quality score; and other information
Interpretation
GUS leaching potential index
6.31 Calculated High leachability
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate
Value
3.18 X 1001 Calculated -
Note
-
Potential for particle bound transport index
Medium Calculated -
Potential for loss via drain flow
Mobile Calculated -
Bio-concentration factor
BCF (l kg⁻¹)
69
Q2 Q = Miscellaneous data from online sources
2 = Unverified data of unknown source
Estimated		 Low potential
CT₅₀ (days)
Not available -
Known metabolites

None
ECOTOXICOLOGY
Terrestrial ecotoxicology
Property
Value
Source; quality score; and other information
Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
1518
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
Rat		 Moderate
Mammals - Short term dietary NOEL
(mg kg⁻¹)
5.4
Q2 Q = Miscellaneous data from online sources
2 = Unverified data of unknown source
Rat		 High
(ppm diet)
- -
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)
- - -
Birds - Acute LD₅₀ (mg kg⁻¹)
1605
F5 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
5 = Verified data used for regulatory purposes
Anas platyrhynchos		 Moderate
Birds - Short term dietary (LC₅₀/LD₅₀)
- - -
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)
- - -
Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)
- - -
Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)
- - -
Soil micro-organisms
- - -
Collembola
Acute LC₅₀ (mg kg⁻¹)
- - -
Chronic NOEC (mg kg⁻¹)
- - -
Non-target plants
- - -
- - -
Honeybees (Apis spp.)
Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
36
F5 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
5 = Verified data used for regulatory purposes
 Moderate
Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
- - -
Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
- - -
Chronic
- - -
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)
- - -
Beneficial insects (Parasitic wasps)
- - -
Beneficial insects (Predatory mites)
- - -
Beneficial insects (Ground beetles)
- - -
Aquatic ecotoxicology
Property
Value
Source; quality score; and other information
Interpretation
Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
12
F5 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
5 = Verified data used for regulatory purposes
Oncorhynchus mykiss		 Moderate
Fish - Chronic 21 day NOEC (mg l⁻¹)
0.999
P3 P = Other non-EU, UK or US Governments and Regulators
3 = Unverified data of known source
Pimephales promelas		 Moderate
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
25.7
F5 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
5 = Verified data used for regulatory purposes
Daphnia magna		 Moderate
Aquatic invertebrates - Chronic 21 day NOEC (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)
0.624
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
Lemna gibba		 Moderate
Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)
> 0.4
F5 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
5 = Verified data used for regulatory purposes
Pseudokirchneriella subcapitata		 Moderate
Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)
0.035
P3 P = Other non-EU, UK or US Governments and Regulators
3 = Unverified data of known source
Chlorella fusca 24 hrs		 Moderate
Mesocosm study data
NOEAEC mg l⁻¹
- - -
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)
1518
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
Rat		 Moderate
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
2020
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
Rabbit		 -
Mammals - Inhalation LC₅₀ (mg l⁻¹)
> 0.52
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
Rat		 -
Other Mammal toxicity endpoints
- - -
ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)
- - -
ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)
- - -
AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)
- - -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)
- - -
Dermal penetration studies (%)
- - -
Dangerous Substances Directive 76/464
- - -
Exposure Routes
Public
-
Occupational
-
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
- - -
Health issues
Specific human health issues
Carcinogen
Genotoxic
Endocrine disruptor
XNo, known not to cause a problem
A0 A = Chromosome aberration (EFSA database)
0 = No data
;
B0 B = DNA damage/repair (EFSA database)
0 = No data
;
C0 C = Gene mutation (EFSA database)
0 = No data
;
D0 D = Genome mutation (EFSA database)
0 = No data
;
E3 E = Unspecified genotoxicity type (miscellaneous data source)
3 = Negative
 No data found
Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant
No data found
XNo, known not to cause a problem
 No data found
Respiratory tract irritant Skin irritant Skin sensitiser
✓Yes, known to cause a problem
✓Yes, known to cause a problem
XNo, known not to cause a problem
Eye irritant Phototoxicant  
✓Yes, known to cause a problem
 No data found  
General human health issues
Liver toxicant
Harmful if swallowed
Handling issues
Property
Value and interpretation
General
No information available
CLP classification 2013
Health: H302, H315, H319, H335
Environment: H411
WHO Classification
III (Slightly hazardous)
UN Number
-
Waste disposal & packaging
-
Shelf-life, storage, stability and reactivity
-
TRANSLATIONS
Language
Name
English
prometon
French
prometone
German
Prometon
Danish
prometon
Italian
prometon
Spanish
prometon
Greek
-
Polish
prometon
Swedish
-
Hungarian
-
Dutch
-
Norwegian
-
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