Trifluralin (Ref: EL 152)

Trifluralin (Ref: EL 152)	Last updated: 22/08/2024
(Also known as: trifluraline; treflan)

SUMMARY

Data alerts

The following alerts are based on the data in the tables below. An absence of an alert does not imply the substance has no implications for human health, biodiversity or the environment but just that we do not have the data to form a judgement.

Environmental fate	Ecotoxicity	Human health
Environmental fate High alert: Persistent; Potential for particle bound transport: High	Ecotoxicity High alert: Fish acute ecotoxicity: High	Human health High alert: Endocrine disrupter; Reproduction/development effects

GENERAL INFORMATION

Description

A pre-emergence soil-incorporated herbicide for use in various crops to control many annual grasses and broad-leaved weeds

Example pests controlled

Annual ryegrass; Barnyardgrass; Canary grass; Grabgrass; Wild oats; Redshank; Pigweed; Yellow vine; Wireweed

Example applications

Oilseed rape; Sunflowers; Cotton; Soybeans; Wetch; Linseed; Peanuts; Broccoli; Tomatoes; Cabbage; Carrots; Chicory; Orchards and vineyards

Efficacy & activity

Availability status

Current

Introduction & key dates

1961, registered USA

GB regulatory status

GB COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

GB LERAP status

No UK approval for use as a pesticide

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Greece

Date EC 1107/2009 inclusion expires

Expired

EU Candidate for substitution (CfS)

Not applicable

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

Approved for use (✓) under EC 1107/2009 by Mutual Recognition of Authorisation and/or national regulations in the following EEA countries

ISIceland	NONorway

Additional information

Also used in

Australia, USA

Chemical structure

Isomerism

None

Chemical formula

C₁₃H₁₆F₃N₃O₄

Canonical SMILES

CCCN(CCC)C1=C(C=C(C=C1[N+](=O)[O-])C(F)(F)F)[N+](=O)[O-]

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

ZSDSQXJSNMTJDA-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C13H16F3N3O4/c1-3-5-17(6-4-2)12-10(18(20)21)7-9(13(14,15)16)8-11(12)19(22)23/h7-8H,3-6H2,1-2H3

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
trifluralin	-

General status

Pesticide type

Herbicide

Substance groups

Dinitroaniline herbicide

Minimum active substance purity

950 g kg⁻¹

Known relevant impurities

EU dossier - N-nitroso-di-n-propylamine 1mg kg⁻¹

Substance origin

Synthetic

Mode of action

Selective. Inhibition of mitosis and cell division. Microtubule assembly inhibition.

CAS RN

1582-09-8

EC number

216-428-8

CIPAC number

183

US EPA chemical code

036101

PubChem CID

5569

CLP index number

609-046-00-1

Molecular mass

335.28

PIN (Preferred Identification Name)

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)aniline

IUPAC name

α,α,α-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine

CAS name

2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzenamine

Other status information

OSPAR pfa/soc; WFD priority substance; Chemical subject to PIC regulations

Relevant Environmental Water Quality Standards

EU Directive 2008/105/EC EQS surface waters: annual average 0.03 µg l⁻¹
UK Statutory standard for the protection of aquatic life in inland waters, coastal and territorial waters: 0.1 µg l⁻¹ as annual average

Herbicide Resistance Class (HRAC MoA class)

Herbicide Resistance Class (WSSA MoA class)

Insecticide Resistance Class (IRAC MoA class)

Not applicable

Fungicide Resistance Class (FRAC MOA class)

Not applicable

Examples of recorded resistance

Lolium rigidum, Setaria viridis

Physical state

Orange-yellow crystalline solid

Formulations

Property

Value

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

Bayer CropScience
Dow AgroSciences
Makhteshim-Agan
Syngenta
Elanco
Four Seasons Agribusiness Pty Ltd

Example products using this active

Alpha Trifluralin 48EC
Ardent
Fargro Axit
Treflan
Uranus
Elancolan
F.S.A. Trifluralin 480 Herbicide

Formulation and application details

Usually formulated as an emulsifiable concentrate or granules

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.221

Low

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

250000

Hexane

250000

Toluene

250000

Acetone

142000

Methanol

Melting point (°C)

47.2

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

202

Flashpoint (°C)

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

1.86 X 10⁰⁵

Calculated

Log P

5.27

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data based on LogP

Density (g ml⁻¹)

1.36

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

9.5

Moderately volatile. If applied directly to plants or soil, drift is a concern & mitigation is advisable

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

10.2

Moderately volatile

Volatilisation as max % of applied dose lost

From plant surface

24 hr

From soil surface

24 hr

Volatilisation is potentially a concern for short and long range air transport

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

Neutral solution 209nm = 19400, 272nm = 8460, 385nm = 2440

Surface tension (mN m⁻¹)

71.4

at 24.5°C sat soln

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

133.7

Persistent

DT₅₀ (lab at 20 °C)

133.7

Persistent

DT₅₀ (field)

170

Persistent

DT₉₀ (lab at 20 °C)

602

Very persistent

DT₉₀ (field)

565

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 66.3-161.6 days (normalised), DT₉₀ range 270-1181 days; field studies DT₅₀ range 35-375 days, DT₉₀ range 116-1246 days; Other sources: DT₅₀ 57-126 days (R3), 169 days at 25 °C (R3)

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

4.0

Note

Published literature RL₅₀ range 0.82-9.71 days, 3 field-grown crops, various matrices. n=3

Aqueous photolysis DT₅₀ (days) at pH 7

Value

0.4

Fast

Note

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

Value

Stable

Note

Stable at pH 7 and pH 9, 5% degradation after 5 days at pH 4

Water-sediment DT₅₀ (days)

5.5

Fast

Water phase only DT₅₀ (days)

Moderately fast

Sediment phase only DT₅₀ (days)

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

[Malt: 546 days @ 20-22 DegC, dark conditions; Field study]

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

Non-mobile

K_oc (mL g⁻¹)

15800

Notes and range

Other sources: 105-30903 mL g⁻¹ (R3), Log K_oc 4.14 at 25 °C (R4)

Freundlich

K_f (mL g⁻¹)

79.4

Non-mobile

K_foc (mL g⁻¹)

8765

¹/_n

0.972

Notes and range

EU dossier kf range 18.6-156, K_foc range 6414-13414 mL g⁻¹, ¹/_n range 0.962-0.986, Soils=4; Literature mean: K_f = 62.8 mL.g, K_foc = 4742 mL g⁻¹, ¹/_n = 1.06, Soils = 17

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.13

Calculated

Low leachability

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

Value

6.12 X 10^-03

Calculated

Note

Potential for particle bound transport index

High

Calculated

Potential for loss via drain flow

Non-mobile

Calculated

Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk

5.3

- Calculated using the Atkinson method. Assumed 1.5E+06 OH/cm³, 12 hr

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

5674

High potential

CT₅₀ (days)

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

3-nitro-N2,N2-dipropyl-5-(trifluoromethyl)benzene-1,2-diamine (Ref: TR-4)

Major fraction

0.132

2-ethyl-1-propyl-5-(trifluoromethyl)-1H-benzimidazol

2-ethyl-7-nitro-5-(trifluoromethyl)-1H-benzimidazole

Photolysis

3-nitro-5-(trifluoromethyl)benzene-1,2-diamine

Photolysis

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

2-ethyl-1-propyl-5-(trifluoromethyl)-1H-benzimidazol (Ref: TR-14)

Plant; Sediment

2-ethyl-7-nitro-5-(trifluoromethyl)-1H-benzimidazole (Ref: TR-15)

Surface water

3,5-dinitro-4-(propylamino)-benzoic acid (Ref: TR-22)

Animal (Faeces)

2,2'-diazene-1,2-diylbis[6-nitro-N-propyl-4-(trifluoromethyl)aniline] (Ref: TR-28)

Animal

N2,N2-dipropyl-5-(trifluoromethyl)benzene-1,2,3-triamine (Ref: TR-7)

Sediment

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)

2.4

Rat

High

(ppm diet)

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

> 148

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2250

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

573.9 mg kg bw⁻¹ day⁻¹

Colinus virginianus

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

102.85

Colinus virginianus NOEC

Moderate

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

> 500

Eisenia foetida corr

Moderate

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

14.19

Eisenia foetida corr

Moderate

Soil micro-organisms

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

Dose: 8.5 mg kg⁻¹ soil

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)

> 100

Apis mellifera

Low

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

> 100

Apis mellifera

Low

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

Chronic

Notes

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 at dose 60 g ha⁻¹

Chrysoperla carnea

Beneficial insects (Parasitic wasps) as % Mortality at dose 1.2 kg ha⁻¹

84.8

Aphidius rhopalosiphi Adult

Beneficial insects (Predatory mites) as % Mortality at dose 1.2 kg ha⁻¹

58.9

Typhlodromus pyri Protonymph

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)

0.088

Oncorhynchus mykiss

High

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

Pimephales promelas 35 day

Moderate

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

0.21

Danio rerio EC₅₀ Embryo

Moderate

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

0.245

Daphnia magna

Moderate

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

0.051

Daphnia magna

Moderate

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

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

0.074

Americamysis bahia

High

Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)

1.0

Chironomus riparius 2 day

Moderate

Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)

0.25

Chironomus riparius

Moderate

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

810

Chironomus riparius

Low

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

0.0435

Lemna gibba

Moderate

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

0.0122

Raphidocelis subcapitata

Moderate

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

0.005

Unknown species

Moderate

Mesocosm study data

NOEAEC mg l⁻¹

Marine bivalves

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)

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 1.252

Rat 4 hr (head only)

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)

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)

0.026

Dermal penetration studies (%)

default

Dangerous Substances Directive 76/464

List II

Exposure Routes

Public

Bystanders may be exposed briefly but risk considered low

Occupational

No unacceptable risks to operators or other workers identified

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

Drinking Water Standards

Non-statutory WHO drinking water guideline 0.02 mg l⁻¹

UK EA QS database 2018

Drinking Water MAC (μg l⁻¹)

Mammalian dose elimination route and rate

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

No data found

General human health issues

Blood, liver and kidney toxicant
May cause respiratory depression
IARC Group 3 carcinogen - not classifiable; US EPA - possible human carcinogen; CLP data - suspected carcinogen
Endocrine issues - Interaction withs pregnane X cellular receptor

Handling issues

Property

Value and interpretation

General

Prevent generation of dust
Not explosive
Not expected to auto-ignite; Not highly flammable
IMDG Transport Hazard Class 9

CLP classification 2013

Health: H317, H351
Environment: H400, H410

WHO Classification

U (Unlikely to present an acute hazard)

UN Number

UN3077

Waste disposal & packaging

Packaging Group III (minor danger)

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

trifluralin

French

trifluraline

German

Trifluralin

Danish

trifluralin

Italian

trifluralin

Spanish

trifluralina

Greek

Polish

trifluralina

Swedish

Hungarian

trifluralin

Dutch

rifluraline

Norwegian

Record last updated:	22/08/2024
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