Prometon (Ref: G 31435)

Prometon (Ref: G 31435)	Last updated: 27/11/2019
(Also known as: prometone; 2,4-prometone)

SUMMARY

Prometon is a non-selective herbicide without EU regulatory approval for use. 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.

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

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

Also used in

USA

Chemical structure

Isomerism

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 group

Methoxytriazine

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

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)

Herbicide Resistance Classification (WSSA)

Insecticide Resistance Classification (IRAC)

Not applicable

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Physical state

White crystalline powder

Related substances & organisms

butan-1-ol

ethylene glycol

atraton

Formulations

Property

Value

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

Pramitol
Primatol
Gesafram

Example products using this active

Ciba-Geigy Group
Makhteshim Agan

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

High

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

250000

Benzene

500000

Acetone

500000

Methanol

250000

Toluene

Melting point (°C)

91.5

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

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

8.13 X 10⁰²

Calculated

Log P

2.91

Moderate

Bulk density (g ml⁻¹)

1.088

Dissociation constant pKa) at 25 °C

9.73

Weak acid

Vapour pressure at 20 °C (mPa)

0.306

Low volatility

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

4.38 X 10^-04

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

Very persistent

DT₅₀ (lab at 20 °C)

932

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

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

K_d

0.16

Mobile

K_oc

43.2

Notes and range

Literature data: K_d range 0.15-0.17 mL g⁻¹, koc rnage 34.9-51.5 mL g⁻¹, soils=2; Other sources Log K_oc 2.54 at 25 °C (R3)

Freundlich

K_f

0.29

Moderately mobile

K_foc

75.2

¹/_n

0.918

Notes and range

Literature data: K_f 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

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

Estimated

Low potential

CT₅₀ (days)

Not available

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

1518

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

5.4

Rat

High

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

1605

Anas platyrhynchos

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.999

Pimephales promelas

Moderate

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

25.7

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

Lemna gibba

Moderate

Non-target plants

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

> 0.4

Pseudokirchneriella subcapitata

Moderate

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

0.035

Chlorella fusca 24 hrs

Moderate

Honeybees (Apis spp.)

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

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)

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)

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

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

Soil micro-organisms

Mesocosm study data

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

Rat

Moderate

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

2020

Rabbit

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 0.52

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

European MRLs

EU MRL pesticide database

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

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

EC Risk Classification

Xn - Harmful: R22
Xi - Irritant: R36/37/38

EC Safety Classification

S26, S36

WHO Classification

III (Slightly hazardous)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

prometon

French

prometone

German

Prometon

Danish

prometon

Italian

prometon

Spanish

prometon

Greek

Polish

prometon

Swedish

Hungarian

Dutch

Record last updated:	27/11/2019
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