Triflumuron (Ref: OMS 2015)

Triflumuron (Ref: OMS 2015)	Last updated: 20/03/2021
(Also known as: SIR 8514)

GENERAL INFORMATION

Description

An insecticide used to protect against a range of insect pests. It is also used as an ecoparasitic treatment in veterinary medicine.

Example pests controlled

Flea larvae; Immature cockroaches; Sliverfish; Lice; Miosquitoes; beetles

Example applications

Fruit including apples, pears, nectarines, peaches; Non-cropped situations including households, commercial and industrial sites

Efficacy & activity

Availability status

Current

Introduction & key dates

circa 1980

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

Approved

Dossier rapporteur/co-rapporteur

Italy/Hungary

Date EC 1107/2009 inclusion expires

31/03/2021

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

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

No data

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

Pesticide type

Insecticide, Larvicide, Veterinary substance

Substance group

Benzoylurea

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

Chitin synthesis inhibitor, Insect growth regulator

CAS RN

64628-44-0

EC number

264-980-3

CIPAC number

548

US EPA chemical code

118201

PubChem CID

47445

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

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

Cydia pomonella, Plutella xylostella

Physical state

Colourless crystalline powder

Related substances & organisms

triadimenol

Formulations

Property

Value

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

Alsystin
Joice
Altin
Baycidal

Example products using this active

Bayer CropScience
AgroCare

Formulation and application details

Often supplied as a suspension concentrate that is mixed with water and used as a spray but available in many other formulations such as pour-ons.

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)

Not expected to self ignite; Not highly flammable

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

7.94 X 10⁰⁴

Calculated

Log P

4.9

High

Bulk 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

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

249nm =14940000

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)

4.3

Non-persistent

DT₅₀ (field)

Non-persistent

DT₉₀ (lab at 20 °C)

25.2

Non-persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

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

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

15.5

Note

Published literature RL₅₀ range 3.0-39.0 days, fruit of 3 field & undercover crops, n=3; RL₅₀=77 days for pears in cold storage

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

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

44.1

Slightly mobile

K_oc

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

61.6

Non-mobile

K_foc

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

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

Slightly mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

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

Soil

0.231

Major fraction, Relevant

2-chlorobenzoic acid (Ref: AE-C500233)

0.235

Major fraction, Relevant

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

612

Threshold for concern

CT₅₀ (days)

1.36

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 5000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat 2 year

(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)

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 0.021

Lepomis macrochirus

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.023

Pimephales promelas

Moderate

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

0.0016

Daphnia magna

High

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

0.000032

Daphnia magna

High

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)

Non-target plants

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

> 0.025

Scenedemus subspicatus

Moderate

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)

> 200

Low

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

> 226

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)

> 500

Eisenia foetida corr

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

13 / 16

Mortality / Reproduction [Dose: 0.3 kg ha⁻¹]
Aphidius rhopalosiphi

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

14 / 7.3

Mortality / Reproduction [Dose: 0.384 kg ha⁻¹]
Typhlodromus pyri

Soil micro-organisms

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

Dose: 3.3 mg kg⁻¹ soil 28 days

Mesocosm study data

NOEAEC mg l⁻¹

0.0001

Aquatic community

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)

> 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

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

; ; ; ;

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

CLP classification 2013

Health: H330

EC Risk Classification

N - Dangerous for the environment: R50/53

EC Safety Classification

None

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

triflumuron

French

triflumuron

German

Triflumuron

Danish

triflumuron

Italian

triflumuron

Spanish

triflumuron

Greek

Polish

triflumuron

Swedish

triflumuron

Hungarian

triflumuron

Dutch

Record last updated:	20/03/2021
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