Ametryn (Ref: G 34162 )

Ametryn (Ref: G 34162 )	Last updated: 24/12/2020
(Also known as: ametryne)

SUMMARY

Ametyn is a triazine herbicide that no longer has EU regulatory approval for use. It is moderately soluble in water but much more so in organic solvents. It is quite volatile and not expected to leach to groundwater. It is moderately persistant in soils and can persist for a long time in water under certain conditions. It is moderately toxic to mammals and a recognised irritant. Ametryn is moderately toxic to most aquatic organisms, honey bees and earthworms but less so to birds.

GENERAL INFORMATION

Description

A triazine herbicide used to control most annual and broad-leaved weeds

Example pests controlled

Burmuda grass, wiregrass, goosegrass, crabgrass and other grass weeds; Broad-leaved weeds including dallisgrass, thistle, purslane, pigweed, cocklebur, lambsquarters, morning glory and foxtail

Example applications

Fruit including citrus, bananas; Corn; Potatoes; Sugarbeet

Efficacy & activity

Availability status

Current

Introduction & key dates

1964, first registered USA

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

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

Date EC 1107/2009 inclusion expires

Expired

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

Also used in

Australia

Chemical structure

Isomerism

Chemical formula

C₉H₁₇N₅S

Canonical SMILES

CCNC1=NC(=NC(=N1)SC)NC(C)C

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

RQVYBGPQFYCBGX-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C9H17N5S/c1-5-10-7-12-8(11-6(2)3)14-9(13-7)15-4/h6H,5H2,1-4H3,(H2,10,11,12,13,14)

2D structure diagram/image available?

Yes

General status

Pesticide type

Herbicide

Substance group

Triazine

Minimum active substance purity

96%

Known relevant impurities

Substance origin

Synthetic

Mode of action

Selective, systemic absorbed through foliage and roots. Inhibits photosynthesis (photosystem II).

CAS RN

834-12-8

EC number

212-634-7

CIPAC number

133

US EPA chemical code

080801

PubChem CID

13263

Molecular mass

227.12

PIN (Preferred Identification Name)

N2-ethyl-6-(methylsulfanyl)-N4-(propan-2-yl)-1,3,5-triazine-2,4-diamine

IUPAC name

N2-ethyl-N4-isopropyl-6-methylthio-1,3,5-triazine-2,4-diamine

CAS name

N-ethyl-N'-(1-methylethyl)-6-(methylthio)-1,3,5-triazine-2,4-diamine

Other status information

Chemical subject to PIC regulations

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 powder

Related substances & organisms

atrazine

2,4-D

diuron

simazine

Formulations

Property

Value

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

Ametrex
Evik
Gesapax
Almulex
Duroplant

Example products using this active

Syngenta Crop Protection
FCC
King Tech Corp
Ciba-Geigy
Makhteshim-Agan

Formulation and application details

Available in a range of formulations including emulsifiable concentrates, flowable concentrates and wettable powders.

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

200

Moderate

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

56900

Acetone

1400

n-Hexane

4600

Toluene

Melting point (°C)

86.7

Boiling point (°C)

337

Degradation point (°C)

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

4.27 X 10⁰²

Calculated

Log P

2.63

Low

Bulk density (g ml⁻¹)

1.18

Dissociation constant pKa) at 25 °C

10.07

Very weak acid

Vapour pressure at 20 °C (mPa)

0.365

Low volatility

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

4.10 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)

Moderately persistent

DT₅₀ (lab at 20 °C)

Moderately persistent

DT₅₀ (field)

Moderately persistent

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

Other sources: DT₅₀ 70-120 days (R3)

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

Slow degradation in UV light

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

Value

Stable

Note

Stable to hydrolysis except at extreme pH values e.g. pH 0-1 and pH 13-14.

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

Moderately mobile

K_oc

316

Notes and range

General literature K_oc range 170-390 mL g⁻¹

Freundlich

K_f

76.81

Non-mobile

K_foc

5115

¹/_n

0.86

Notes and range

K_f range 1.35-194.6 mL g⁻¹, K_foc range 38.6-14969 mL g⁻¹, ¹/_n range 0.60-1.22, Soils=3

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.46

Calculated

Low leachability

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

Value

9.47 X 10^-03

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

deethyl ametryne

Soil

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

Low potential

CT₅₀ (days)

Not available

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

1009

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 5620

Anas platyrhynchos

Low

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)

0.70

Pimephales promelas 35 day

Moderate

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

Daphnia magna

Moderate

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

0.32

Daphnia magna LOEC

Moderate

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

1.7

Americamysis bahia

Moderate

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)

0.01

Lemna perpusilla 7 day

Moderate

Non-target plants

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

0.0036

Raphidocelis subcapitata

High

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

Honeybees (Apis 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)

> 100

Low

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)

166

Moderate

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)

1009

Rat

Moderate

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

2020

Rabbit

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.03

Rat

Other Mammal toxicity endpoints

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

0.015

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

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

No data found

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Slightly toxic

Handling issues

Property

Value and interpretation

General

No information available

CLP classification 2013

Health: H302
Environment: H400, H410

EC Risk Classification

Xn - Harmful: R22
N - Dangerous for the environment: R50, R53

EC Safety Classification

S2, S36, S61, S60

WHO Classification

II (Moderately hazardous)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

ametryn

French

ametryne

German

Ametryn

Danish

ametryn

Italian

ametrina

Spanish

ametrina

Greek

ametryn

Polish

ametryna

Swedish

Hungarian

Dutch

ametryn

Record last updated:	24/12/2020
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