Triflumizole (Ref: NF 114 )

Triflumizole (Ref: NF 114 )	Last updated: 17/03/2024
(Also known as: trifmine)

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 Moderate alert: Drainflow: Slightly mobile; Potential for particle bound transport: Medium Warning: Significant data are missing	Ecotoxicity Moderate alert: Fish acute ecotoxicity: Moderate; Fish chronic ecotoxicity: Moderate; Daphnia acute ecotoxicity: Moderate; Daphnia chronic ecotoxicity: Moderate; Bees acute contact ecotoxicity: Moderate; Bees acute oral ecotoxicity: Moderate	Human health High alert: Reproduction/development effects

GENERAL INFORMATION

Description

A fungicide used to control fungal diseases on top fruit, grapes and other crops

Example pests controlled

Powdery mildew; Scab; Cedar apple rust; Blossom blight & fruit rot; Leaf spot

Example applications

Cucumbers; Vegetables including corgettes, gherkins, broccoli, chinese cabbage, Kale, collards; Tomatoes; Ornamentals; Fruit including grapes, melons, apples, pears

Efficacy & activity

Availability status

Current

Introduction & key dates

1986, first registered Japan

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

Netherlands/Belgium

Date EC 1107/2009 inclusion expires

Expired

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
		✓

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

Chemical structure

Isomerism

None

Chemical formula

C₁₅H₁₅ClF₃N₃O

Canonical SMILES

CCCOCC(=NC1=C(C=C(C=C1)Cl)C(F)(F)F)N2C=CN=C2

Isomeric SMILES

International Chemical Identifier key (InChIKey)

HSMVPDGQOIQYSR-KGENOOAVSA-N

International Chemical Identifier (InChI)

InChI=1S/C15H15ClF3N3O/c1-2-7-23-9-14(22-6-5-20-10-22)21-13-4-3-11(16)8-12(13)15(17,18)19/h3-6,8,10H,2,7,9H2,1H3/b21-14+

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
triflumizole	-

General status

Pesticide type

Fungicide

Substance groups

Conazole fungicide

Minimum active substance purity

980 g kg⁻¹

Known relevant impurities

EU dossier - toluene 1g kg⁻¹

Substance origin

Synthetic

Mode of action

Systemic with protective and curative action. Inhibitors of chitin biosynthesis.

CAS RN

99387-89-0

Alternative/old CAS RN

68694-11-1

EC number

614-708-8

CIPAC number

730

US EPA chemical code

128879

PubChem CID

91699

CLP index number

612-289-00-6

Molecular mass

345.75

PIN (Preferred Identification Name)

(1E)-N-[4-chloro-2-(trifluoromethyl)phenyl]-1-(1H-imidazol-1-yl)-2-propoxyethan-1-imine

IUPAC name

(E)-4-chloro-α,α,α-trifluoro-N-(1-imidazol-1-yl-2-propoxyethylidene)-o-toluidine

CAS name

1-[(1E)-1-[[4-chloro-2-(trifluoromethyl)phenyl]imino]-2-propoxyethyl]-1H-imidazole

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Class (HRAC MoA class)

Not applicable

Herbicide Resistance Class (WSSA MoA class)

Not applicable

Insecticide Resistance Class (IRAC MoA class)

Not applicable

Fungicide Resistance Class (FRAC MOA class)

Examples of recorded resistance

Physical state

White granules

Formulations

Property

Value

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

Chemtura
Nippon Soda

Example products using this active

Rocket EC
Procure
Trifmine

Formulation and application details

Usually suppplied as an emulsifiable concentrate that is mixed with water and used as a spray

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

10.5

Low

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

1486000

Ethyl acetate

17600

n-Hexane

496000

Methanol

1440000

Acetone

Melting point (°C)

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

150

Flashpoint (°C)

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

5.89 X 10⁰⁴

Calculated

Log P

4.77

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies

Density (g ml⁻¹)

1.35

Dissociation constant pKa) at 25 °C

3.7

at 25 °C

Weak base

Vapour pressure at 20 °C (mPa)

0.191

at 25 °C

Low volatility. If applied directly to plants, drift is a concern & mitigation is advisable

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

6.29 X 10^-03

at 25 °C

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

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

201.5nm = 25300
236nm = 26400
301nm = 4910

Surface tension (mN m⁻¹)

49.4

at 20°C 90% soln

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)

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

Best available data

Dissipation rate RL₅₀ (days) on plant matrix

Value

Note

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

Note

Aqueous photolysis DT₅₀ (days) at pH 7

Value

5.9

Moderately fast

Note

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

Value

68.2

at 25 °C

Moderately persistent

Note

pH sensitive: DT₅₀ 18.5 hrs at pH 3, 4.6 days at pH 9, all at 20 °C and 0.5 mg l⁻¹

Water-sediment DT₅₀ (days)

81.3

Moderately fast

Water phase only DT₅₀ (days)

2.7

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

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

Slightly mobile

K_oc (mL g⁻¹)

1373

Notes and range

Freundlich

K_f (mL g⁻¹)

K_foc (mL g⁻¹)

¹/_n

Notes and range

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.96

Calculated

Low leachability

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

Value

1.53 X 10^-02

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

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

11.7

Calculated using the Atkinson method. Assumed 1.5E+06 OH/cm³, 24 hr

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

1417

Threshold for concern

CT₅₀ (days)

5.8

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

4-chloro-2-(trifluoromethyl)aniline (Ref: FA-1-1)

Major fraction

0.234

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

(1E)-N'-[4-chloro-2-(trifluoromethyl)phenyl]-2-hydroxyethanimidamide

FM-8-1

2-amino-5-chloro-3-(trifluoromethyl)phenol

FA-1-5

imidazole

N-[4-chloro-2-(trifluoromethyl)phenyl]-2-hydroxyacetamide

FD-2-1

N-[4-chloro-2-(trifluoromethyl)phenyl]-2-(2-methylpropoxy)acetamide

FD-6-1

Plant

N-(4-chloro-2-trifluoromethylphenyl)-oxalamic acid

FD-7-1

(1E)-N'-[4-chloro-2-(trifluoromethyl)phenyl]-2-propoxyethanimidamide

FM-1-6

N-[4-chloro-2-(trifluoromethyl)phenyl]-2-propoxyacetamide

FD-1-1

(2E)-2-{[4-chloro-2-(trifluoromethyl)phenyl]imino}-2-(1H-imidazol-1-yl)ethanol

FM-2-1

(1E)-N'-[4-chloro-2-(trifluoromethyl)phenyl]-N-formyl-2-propoxyethanimidamide

FM-5-1

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

1057

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

4.1

Rat

High

(ppm diet)

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2510

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 1428 mg kg bw⁻¹ day⁻¹

Anas platyrhynchos

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

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

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

Soil micro-organisms

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)

Apis mellifera

Moderate

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

Apis mellifera

Moderate

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)

Beneficial insects (Parasitic wasps) as Mortality LR₅₀ g ha⁻¹

165

Aphidius rhopalosiphi Adult

Beneficial insects (Predatory mites) as Mortality LR₅₀ g 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)

0.57

Oncorhynchus mykiss

Moderate

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

0.044

Pimephales promelas 35 day

Moderate

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

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

2.11

Daphnia magna

Moderate

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

0.18

Daphnia magna

Moderate

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)

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)

1.66

Scenedesmus subspicatus

Moderate

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

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)

1057

Rat

Moderate

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

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 3.6

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.05

Rat SF=100

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

0.1

Rat SF=100

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

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

0.05

Rat SF=100

Dermal penetration studies (%)

4-11

concentration dependent

Dangerous Substances Directive 76/464

List II

Exposure Routes

Public

Negligible risk to bystanders for intended uses

Occupational

Potential risks to operators and other workers mainly due to dermal exposure have been identified under worse case conditions

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

GB MRL expected to deviate from the EU MRL in mid-2023

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

0.1

EU Dir 89/778/EC limit; Calc MAC=36 µg l⁻¹

Mammalian dose elimination route and rate

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

Possible liver toxicant

Handling issues

Property

Value and interpretation

General

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

CLP classification 2013

Health: H302, H317, H360d, H373
Environment: H400, H410

WHO Classification

II (Moderately hazardous)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

triflumizole

French

triflumizole

German

Triflumizol

Danish

triflumizol

Italian

triflumizolo

Spanish

triflumizol

Greek

Polish

triflumizol

Swedish

Hungarian

triflumizol

Dutch

triflumizool

Norwegian

Record last updated:	17/03/2024
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