Glyphosate trimesium

Glyphosate trimesium	Last updated: 09/02/2021
(Also known as: trimethylsulfonium glyphosate)

SUMMARY

Glyphosate trimesium is a non-selective common and effective herbicide. It is highly soluble in water, non-volatile and does not normally leach to groundwater. It is not persistent in soils but may be in aquatic systems under certain conditions. It is moderately toxic to humans and a skin and eye irritant. It is moderately toxic to birds, most aquatic organisms, earthworms and honeybees.

GENERAL INFORMATION

Description

A herbicide used in a wide range of cropping, utility and industrial situations for broad-spectrum control of weeds and grases

Example pests controlled

Annual and perennial weeds, Broad-leaved weeds, Grasses

Example applications

Cereals; Soybeans; Glyphosate tolerant crops; Horticulture; Forestry; Domestic gardens, lawns

Efficacy & activity

Availability status

Current

Introduction & key dates

1971, first reported; 1989, introduced in Spain

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

15/12/2025

UK LERAP status

None (may vary with mixtures)

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Germany/Slovakia

Date EC 1107/2009 inclusion expires

15/12/2022

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, USA

Chemical structure

Isomerism

Chemical formula

C₆H₁₆NO₅PS

Canonical SMILES

C[S+](C)C.C(C(=O)O)NCP(=O)(O)[O-]

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

RUCAXVJJQQJZGU-UHFFFAOYSA-M

International Chemical Identifier (InChI)

InChI=1S/C3H8NO5P.C3H9S/c5-3(6)1-4-2-10(7,8)9;1-4(2)3/h4H,1-2H2,(H,5,6)(H2,7,8,9);1-3H3/q;+1/p-1

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
glyphosate	Parent

General status

Pesticide type

Herbicide

Substance group

Glycine derivative

Minimum active substance purity

950 g kg⁻¹ as acid

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Broad-spectrum, systemic, translocated and non-residual. Inhibition of EPSP synthase.

CAS RN

81591-81-3

EC number

213-997-4

CIPAC number

284

US EPA chemical code

128501

PubChem CID

105048

Molecular mass

245.23

PIN (Preferred Identification Name)

trimethylsulfonium N-[(hydroxyphosphinato)methyl]glycine

IUPAC name

trimethylsulfonium N-[(hydroxyphosphinato)methyl]glycine

CAS name

2-(phosphonomethylamino)acetate; trimethylsulfonium

Other status information

Risk of herbicide resistance developing - anti-resistance management required; PAN listed Highly Hazardous Chemical

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

Eleusine indica, Euphorbia heterophylla

Physical state

White solid

Related substances & organisms

8-hydroxyquinoline

Formulations

Property

Value

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

Coloso
Ouragan
Zapp

Example products using this active

Monsanto
Syngenta

Formulation and application details

Often supplied as a soluble concentrate that is mixed with water and applied as a spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

1050000

High

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

Acetone

Xylene

Heptane

174000

Methanol

Melting point (°C)

Decomposes before melting

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

1.26 X 10^-03

Calculated

Log P

-2.9

Low

Bulk density (g ml⁻¹)

1.42

Dissociation constant pKa) at 25 °C

Fully dissociated in water

Vapour pressure at 20 °C (mPa)

0.00000001

Low volatility

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

2.0 X 10^-09

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)

Non-persistent

DT₅₀ (lab at 20 °C)

Non-persistent

DT₅₀ (field)

Non-persistent

DT₉₀ (lab at 20 °C)

144

Persistent

DT₉₀ (field)

149

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 3-62days, DT₉₀ range 81-207 days, field studies DT₅₀ range 1.5-34 days USA and Germany, DT₉₀ range 76-326 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

Stable

Note

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

Value

Stable

Note

Stable pH 5 to pH 9 up to 50 °C

Water-sediment DT₅₀ (days)

183

Slow

Water phase only DT₅₀ (days)

Slow

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

0.93

Non-mobile

K_foc

27621

¹/_n

0.97

Notes and range

EU dossier K_foc 530-180000 mL g⁻¹, ¹/_n range 0.84-1.1

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-0.59

Calculated

Low leachability

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

Value

5.35 X 10^-03

Calculated

Note

Estimated concentrations of chemicals with Koc values greater than 9995 ml g⁻¹ are beyond the scope of the regression data used in SCI-GROW development. If there are concerns for such chemicals, a higher tier groundwater exposure assessment should be considered, regardless of the concentration returned by SCI-GROW

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

aminomethylphosphonic acid

Soil

0.154

Major fraction, Relevant

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

Low risk

Based on LogP < 3

Low risk

CT₅₀ (days)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

748

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

950

Unknown species

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5000 mg kg feed⁻¹

Unknown species

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

1800

Oncorhynchus mykiss

Low

Fish - Chronic 21 day NOEC (mg l⁻¹)

Oncorhynchus mykiss

Low

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

Unknown species

Moderate

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

1.1

Unknown species

Moderate

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

16.0

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)

Unknown species

Low

Non-target plants

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

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

0.72

Unknown species

Moderate

Honeybees (Apis spp.)

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

> 400

Low

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

> 400

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)

> 1000

Eisenia foetida

Low

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

28.8

Eisenia foetida

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

8400

48 hour
Aphidius rhopalosiphi

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

5089

Typhlodromus pyri

% Effect

Soil micro-organisms

Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect

Dose: 18 kg ha⁻¹

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)

748

Rat

Moderate

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.0

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.5

ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)

0.5

AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)

0.2

Dermal penetration studies (%)

1.0

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

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

No data found

General human health issues

IARC group 2A carcinogen
Possible bladder and liver toxicant

Handling issues

Property

Value and interpretation

General

IMDG Transport Code is usually 9

CLP classification 2013

Health: H302
Environment: H411

EC Risk Classification

Xn - Harmful: R22
N - Dangerous for the environment: R51, R53

EC Safety Classification

S2, S36/37, S46, S61

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

Variable with product, usually 3077 or 3082

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

glyphosate trimesium

French

German

Danish

Italian

Spanish

Greek

Polish

glifosat-trimesium

Swedish

Hungarian

Dutch

Record last updated:	09/02/2021
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