Triflumuron (Ref: OMS 2015)

Triflumuron (Ref: OMS 2015)	Last updated: 31/10/2024
(Also known as: SIR 8514)

GENERAL INFORMATION

Description

An antiparasitic benzoylurea insecticide used in veterinary medicine

Availability status

Current

Introduction & key dates

circa 1980, introduced; 1993, first approved in Australia for veterinary use

Examples of veterinary uses

Used to control lice, flies and ticks

Examples of species treated

Sheep; Poultry

Approval status

VMR 2013/2033 approval status (GB/UK)

Not approved

EU Regulatory approval status

Not approved

Chemical structure

Isomerism

None

Chemical formula

C₁₅H₁₀ClF₃N₂O₃

Canonical SMILES

C1=CC=C(C(=C1)C(=O)NC(=O)NC2=CC=C(C=C2)OC(F)(F)F)Cl

Isomeric SMILES

International Chemical Identifier key (InChIKey)

XAIPTRIXGHTTNT-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C15H10ClF3N2O3/c16-12-4-2-1-3-11(12)13(22)21-14(23)20-9-5-7-10(8-6-9)24-15(17,18)19/h1-8H,(H2,20,21,22,23)

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
triflumuron	-

General status

Veterinary substance type

Insecticide, Ectoparasiticide

Substance groups

Benzoylurea insecticide; Urea insecticide

Minimum active substance purity

980 g kg⁻¹

Known relevant impurities

EU dossier - N,N'-bis-(4-(trifluoromethoxy)pheny) urea 1g kg⁻¹, 4-trifluoro-methoxyaniline 5g kg⁻¹, toluene

Substance origin

Synthetic

Mode of action

Inhibitor of chitin biosynthesis affecting CHS1.

Molecular targets

CAS RN

64628-44-0

EC number

264-980-3

CIPAC number

548

US EPA chemical code

118201

PubChem CID

47445

CLP index number

No data found

Therapeutic Class

ATCvet Code

None allocated

Controlled Drug?

Regulation 37/2010 MRL Classification

Molecular mass

358.70

PIN (Preferred Identification Name)

2-chloro-N-{[4-(trifluoromethoxy)phenyl]carbamoyl}benzamide

IUPAC name

1-(2-chlorobenzoyl)-3-(4-trifluoromethoxyphenyl)urea

CAS name

2-chloro-N-(((4-(trifluoromethoxy)phenyl)amino)carbonyl)benzamide

Other status information

Evidence of use in third world countries

Relevant Environmental Water Quality Standards

Physical state

Colourless crystalline powder

Formulations

Property

Product

Manufacturer

Authorisation Route

Legal Class (GB/UK)

Example products (past and present) using this active

Clipguard

Novartic Animal Health

Not licensed

Epic Pour On

Jurox

Not licensed

Formulation and application details

Usually formulated for topical use as a pour-on product

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.04

Low

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

11700

Dichloromethane

26600

Acetone

23300

Ethyl acetate

100

n-Heptane

Melting point (°C)

194

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

360

Flashpoint (°C)

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

7.94 X 10⁰⁴

Calculated

Log P

4.9

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies

Density (g ml⁻¹)

1.55

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

0.0002

Low volatility

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

1.79 X 10^-03

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

24 hr

Volatilisation is not considered critical for air pollution

From soil surface

24 hr

Volatilisation is not considered critical for air pollution

Maximum UV-vis absorption L mol⁻¹ cm⁻¹

249nm =14940000

Surface tension (mN m⁻¹)

Refractive Index

Environmental release

Degradation

Property

Value

Source; quality score; and other information

Interpretation

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Non-persistent

DT₅₀ (lab at 20 °C)

4.3

Non-persistent

DT₅₀ (field)

Non-persistent

DT₉₀ (lab at 20 °C)

25.2

Non-persistent

DT₉₀ (field)

Note

EU dossier lab studies DT₅₀ range 1.2-14.6 days, DT₉₀ range 5.7-62.5 days

Manure DT₅₀ (days)

Aqueous photolysis DT₅₀ (days) at pH 7

Value

32.8

Stable

Note

Data for test conditions of continuous irradiation equivalent to 119 days solar summer conditions in Arizona USA (33 deg N) and 185 days Athens, Greece (37 deg N)

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

Value

Stable

Note

Stable at pH 5 and pH 7, DT₅₀ 57 days at pH 9, all at 25 °C

Water-sediment DT₅₀ (days)

6.4

Fast

Water phase only DT₅₀ (days)

2.6

Moderately fast

Air degradation

As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below.

Decay in stored produce DT₅₀

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

44.1

Slightly mobile

K_oc (mL g⁻¹)

2967

Notes and range

EU dossier K_d range 27.9-71.1 mL g⁻¹, K_oc range 2450-3510 mL g⁻¹, Soils=3 for humous sandy soils only

Freundlich

K_f (mL g⁻¹)

61.6

Non-mobile

K_foc (mL g⁻¹)

11981

¹/_n

1.07

Notes and range

EU dossier K_f range 9.8-162 mL g⁻¹, kfoc range 1629-30006 mL g⁻¹, ¹/_n range 0.85-1.24, Soils=5

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

-0.11

Calculated

Low leachability

Bio-concentration factor

BCF (l kg⁻¹)

612

Threshold for concern

CT₅₀ (days)

1.36

Known soil metabolites

Metabolite

Major/Minor fraction

$Click here for further information on Major/Minor fraction$

Estimated maximum occurrence fraction

Notes

(4-trifluoromethoxy)phenyl urea (Ref: IN MK638)

Major fraction

0.231

2-chlorobenzoic acid (Ref: AE-C500233)

Major fraction

0.235

Known groundwater metabolites

None

Other known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat 2 yr

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

561

Colinus virginianus

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

> 805 mg kg bw⁻¹ day⁻¹

Colinus virginianus

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

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

> 500

Eisenia foetida corr

Moderate

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

>= 378

Eisenia foetida

Low

Soil micro-organisms

Nitrogen mineralisation: -25% efect
Carbon mineralisation: No significant adverse effect

Dose: 3.3 mg kg⁻¹ soil 28 Day

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)

> 200

Apis mellifera

Low

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

> 226

Apis mellifera

Low

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) as Mortality LR₅₀ g ha⁻¹

0.3

Chrysoperla carnea

Beneficial insects (Parasitic wasps) as % Mortality at dose 0.3 kg ha⁻¹

Aphidius rhopalosiphi

Beneficial insects (Predatory mites) as % Mortality at dose 0.384 kg ha⁻¹

Typhlodromus pyri

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 0.021

Lepomis macrochirus

High

Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)

0.023

Pimephales promelas

Moderate

Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

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

0.0016

Daphnia magna

High

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

0.000032

Daphnia magna

High

Tropical Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (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)

0.00032

Chironomus riparius EC15

High

Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)

Aquatic plants - Acute 7 day EC₅₀, biomass (mg l⁻¹)

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

> 0.025

Scenedesmus subspicatus

Moderate

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

Mesocosm study data

NOEAEC mg l⁻¹

0.0001

Aquatic community

NOEAEC mg l⁻¹

Marine bivalves – Acute EC₅₀ development (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)

> 5000

Rat

Low

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

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.03

Rat 4 hr (nose only aerosol)

Other Mammal toxicity endpoints

Intraperitoneal LD₅₀ > 5000 mg kg⁻¹

Rat

Subcutaneous LD₅₀ > 5000 mg kg⁻¹

Mouse

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

0.014

Dog SF=100

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

None allocated

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

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

0.036

Rat SF=100

Dermal penetration studies (%)

1.0-5.0

concentrate dependent

Dangerous Substances Directive 76/464

List II

Exposure Routes

Public

No unacceptable risks to bystanders identified

Occupational

No unacceptable risks to operators or other workers identified

Mammalian dose elimination route and rate

Excreted largely as metabolites in the faeces and bile

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

No further information available

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H330

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

triflumuron

French

triflumuron

German

Triflumuron

Danish

triflumuron

Italian

triflumuron

Spanish

triflumuron

Greek

Polish

triflumuron

Swedish

triflumuron

Hungarian

triflumuron

Dutch

Norwegian

Record last updated:	31/10/2024
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