Trimethacarb (Ref: OMS 597)

Trimethacarb (Ref: OMS 597)	Last updated: 11/11/2019
(Also known as: landrin; SD 8530)

SUMMARY

Trimethacarb is an insecticide without EU regulatory approval for use. It is moderately soluble in water, is quite volatile and there is also a slight risk of leaching to groundwater. It is not generally persistent in soil systems. It may degrade quickly via hydrolysis in aquatic systems. It is moderately toxic to mammals but would not be expected to bioaccumulate. It is an acetyl cholinesterase inhibitor and a neurotoxin. It shows a moderate to high level of toxicity to most aquatic species.

GENERAL INFORMATION

Description

An obsolete carbamate insecticide and molluscide which also acts as a bird and mammal repellant

Example pests controlled

Corn rootworms; Birds; Mammals; Store produce insects

Example applications

Stored cereals; Agricultural fields; Forestry

Efficacy & activity

Availability status

Obsolete

Introduction & key dates

UK regulatory status

UK approval status

Not approved

EC Regulation 1107/2009 (repealing 91/414)

EC Directive 91/414 Status

Not approved

Dossier rapporteur/co-rapporteur

Not applicable

Date inclusion expires

Not applicable

EU Candidate for substitution (CfS)

Not applicable

Listed in EU database

Approved for use (✓) or known to be used (#) in the following EU-27 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

Chemical structure

Isomerism

Chemical formula

C₁₁H₁₅NO₂

Canonical SMILES

CC1=CC(=CC(=C1C)C)OC(=O)NC

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

NYOKZHDTNBDPOB-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C11H15NO2/c1-7-5-10(14-11(13)12-4)6-8(2)9(7)3/h5-6H,1-4H3,(H,12,13)

2D structure diagram/image available?

Yes

General status

Pesticide type

Insecticide, Molluscicide, Repellent

Substance group

Carbamate

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Mainly stomach action but has some contact effects, Cholinesterase inhibitor

CAS RN

2686-99-9

EC number

220-245-9

CIPAC number

130

US EPA chemical code

102401

PubChem CID

17592

Molecular mass

193.24

PIN (Preferred Identification Name)

reaction product comprising from 3.5 to 5 parts by mass of 3,4,5-trimethylphenyl methylcarbamate to 1 part by mass of 2,3,5-trimethylphenyl methylcarbamate

IUPAC name

reaction product comprising from 3.5 to 5 parts by mass of 3,4,5-trimethylphenyl methylcarbamate to 1 part by mass of 2,3,5-trimethylphenyl methylcarbamate

CAS name

2,3,5(or 3,4,5)-trimethylphenyl methylcarbamate

Other status information

Phytotoxic to some crop seeds including maize, wheat and rice

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Physical state

Off-white to brown granules

Formulations

Property

Value

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

Broot
Landrin

Example products using this active

Union Carbide

UK LERAP status

No UK approval for use as a pesticide under EC Regulation 1107/2009

Formulation and application details

Usually supplied as a granular formulation

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

Moderate

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

Melting point (°C)

Decomposes before melting

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

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

3.55 X 10⁰²

Calculated

Log P

2.55

Low

Bulk density (g ml⁻¹)

1.05

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C

6.8

Moderately volatile

Henry's law constant at 25 °C

4.38 X 10^-03

Non-volatile

GUS leaching potential index

2.38

Calculated

Transition state

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

Value

1.30 X 10^-01

Calculated

Note

Potential for particle bound transport index

Low

Calculated

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)

Moderately persistent

DT₅₀ (field)

Moderately persistent

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

General literature states DT₅₀ 14 days in moist sand and 60 days in sterile soil and 42 days in dry, aerated soils

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

Moderately persistent

Note

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

400

Notes and range

Freundlich

K_f

K_foc

¹/_n

Notes and range

pH sensitivity

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

3,5-dimethyl-4-(hydroxymethyl)phenyl N-methylcarbamate

Soil

Major

4,5-dimethyl-3-(hydroxymethyl)phenyl N-methylcarbamate

Soil

2,5-dimethyl-3-(hydroxymethyl)phenyl N-methylcarbamate

Soil

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)

566

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

Birds - Acute LD₅₀ (mg kg⁻¹)

238

Colinus virginianus

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 1.0

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

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

> 18

Daphnia magna

Moderate

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

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

> 0.032

Americamysis bahia

High

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)

Non-target plants

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

> 25

Estimated

Low

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)

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)

47.9

Moderate

Mode of exposure

F3 Nomia melanderi

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)

Low (class I)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

566

Rat

Moderate

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

Mammals - Inhalation LC₅₀ (mg l⁻¹)

Other Mammal toxicity endpoints

Acute percutanous LD₅₀ > 2000 mg kg⁻¹

Rats

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

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Ingestion may cause typical poisoning symptons and in severe cases, may lead to convulsions and respiratory failure

Handling issues

Property

Value and interpretation

General

No information available

CLP classification 2013

Not classified: Obsolete

EC Risk Classification

Not classified: Obsolete

EC Safety Classification

Not classified: Obsolete

WHO Classification

O (Obsolete substance)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

trimethacarb

French

trimethacarbe

German

Trimethacarb

Danish

trimethacarb

Italian

trimetacarb

Spanish

trimetacarb

Greek

Polish

trimetakarb

Swedish

Hungarian

Dutch

Record last updated:	11/11/2019
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