Trifloxystrobin (Ref: CGA 279202)

Trifloxystrobin (Ref: CGA 279202)	Last updated: 22/08/2024
(Also known as: HSDB 7276)

SUMMARY

Trifloxystrobin is a widely used fungicide. It has a low aqueous solubility, a low volatility and, based on its chemical properties, would not normally be expected to leach to groundwater. It would not be expected to be persistent in soil or water systems. It has a low mammalian oral toxicity but there is some evidence that it may cause negative reproduction or fertility effects. It is highly toxic to bird, fish and aquatic invertebrates, but less toxic to honeybees and earthworms.

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	Ecotoxicity High alert: Fish acute ecotoxicity: High; Fish chronic ecotoxicity: High; Daphnia acute ecotoxicity: High; Daphnia chronic ecotoxicity: High	Human health High alert: Reproduction/development effects

GENERAL INFORMATION

Description

A Strobilurin foliar applied fungicide for control of certain foliar, stem and root diseases

Example pests controlled

Alternaria; Black root; Black spot; Botrytis; Downy mildew; Powdery mildew; Leaf spot; Rust; Rhizoctonia stem & root rot; Scab; Blossom blight

Example applications

Cereals; Ornamentals; Vegetables including carrots, asparagus, curcubits, fruiting vegetables, root vegetables (except radish); Fruit including apples, pears, grapes, strawberries; Tropical crops

Efficacy & activity

Wheat/Mildew=Low; Wheat/Septoria=Low; Wheat/Rust=Low; Barley/Rhynchosporium=Low; Barley/Rust=Moderate

Availability status

Current

Introduction & key dates

1999, registered South Africa and USA

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

31/07/2033

GB LERAP status

Check label - may vary with formulation

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Croatia/Germany

Date EC 1107/2009 inclusion expires

31/07/2033

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, Iran, Morocco

Chemical structure

Isomerism

Exists as four geometric isomers: EE, EZ, ZE, and ZZ

Chemical formula

C₂₀H₁₉F₃N₂O₄

Canonical SMILES

CC(=NOCC1=CC=CC=C1C(=NOC)C(=O)OC)C2=CC(=CC=C2)C(F)(F)F

Isomeric SMILES

C/C(=N\OCC1=CC=CC=C1/C(=N\OC)/C(=O)OC)/C2=CC(=CC=C2)C(F)(F)F

International Chemical Identifier key (InChIKey)

ONCZDRURRATYFI-TVJDWZFNSA-N

International Chemical Identifier (InChI)

InChI=1S/C20H19F3N2O4/c1-13(14-8-10-16(11-9-14)20(21,22)23)24-29-12-15-6-4-5-7-17(15)18(25-28-3)19(26)27-2/h4-11H,12H2,1-3H3/b24-13+,25-18+

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
trifloxystrobin	Unstated isomer

General status

Pesticide type

Fungicide

Substance groups

Strobilurin fungicide; Methoxyiminoacetate strobilurin fungicide

Minimum active substance purity

980 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Broad spectrum with preventative and curative action. Respiration inhibitor (QoL fungicide).

CAS RN

141517-21-7

EC number

604-237-6

CIPAC number

617

US EPA chemical code

129112

PubChem CID

11664966

CLP index number

607-424-00-0

Molecular mass

408.37

PIN (Preferred Identification Name)

methyl (2E)-(methoxyimino)(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)acetate

IUPAC name

methyl (E)-methoxyimino-{(E)-α-[1-(α,α,α-trifluoro-m-tolyl)ethylideneaminooxy]-o-tolyl}acetate

CAS name

methyl (αE)-α-(methoxyimino)-2-(((((1E)-1-(3-(trifluoromethyl)phenyl)ethylidene)amino)oxy)methyl)benzeneacetate

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 solid

Formulations

Property

Value

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

AgriGuard
Bayer CropScience
Pan Agriculture

Example products using this active

Coronet
Jaunt
Nativo
Scorpio
Compass
Twist
Flint
Zato 50 WG
Delaro SC325

Formulation and application details

Often supplied as water dispersible granules that are 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)

0.61

Low

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

500000

Acetone

500000

Ethyl acetate

76000

Methanol

500000

Toluene

Melting point (°C)

72.9

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

285

Flashpoint (°C)

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

3.16 X 10⁰⁴

Calculated

Log P

4.5

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies

Density (g ml⁻¹)

1.36

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

3.40 X 10^-03

Low volatility

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

2.30 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

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

250.7nm = 17500, no absorption between 340-750nm

Surface tension (mN m⁻¹)

65.3

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Not readily biodegradable

Soil degradation (days) (aerobic)

DT₅₀ (typical)

0.34

Non-persistent

DT₅₀ (lab at 20 °C)

0.34

Non-persistent

DT₅₀ (field)

1.69

Non-persistent

DT₉₀ (lab at 20 °C)

Moderately persistent

DT₉₀ (field)

20.9

DT₅₀ modelling endpoint

0.60

Note

EU RAR 2016 lab studies DT₅₀ range 0.13-2.83 days, Soils = 20; field study DT₅₀ range 1.1-2.73 days, DT₉₀ range 10.4-35.6 days, Soils=6

Dissipation rate RL₅₀ (days) on plant matrix

Value

4.3

Note

Published literature RL₅₀ range 1.6-7.0 days, field grown ginseng & peppers, various matrices, n=5

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

4.8

Note

Published literature RL₅₀ range 1.4-12.0 days, 8 field crops, various matrices, n=9

Aqueous photolysis DT₅₀ (days) at pH 7

Value

2.7

Moderately fast

Note

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

Value

Moderately persistent

Note

pH sensitive: DT₅₀ 480 days at pH 5, 40 days at pH 7, 1.2 days at pH 9, all at 25 °C

Water-sediment DT₅₀ (days)

2.4

Fast

Water phase only DT₅₀ (days)

1.1

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)

K_oc (mL g⁻¹)

Notes and range

Freundlich

K_f (mL g⁻¹)

43.5

Slightly mobile

K_foc (mL g⁻¹)

2287

¹/_n

0.96

Notes and range

EU dossier K_f range 11.2-325 mL g⁻¹, K_oc range 1642-3745 mL g⁻¹, Soils=6

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.15

Calculated

Low leachability

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

Value

3.82 X 10^-04

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

Calculated using the Atkinson method

Substance of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

431

Threshold for concern

CT₅₀ (days)

Not available

Known soil metabolites

Metabolite

Major/Minor fraction

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

Estimated maximum occurrence fraction

Notes

(2E)-[({2-[(E)-carboxy(methoxyimino)methyl]benzyl}oxy)imino][3-(trifluoromethyl)phenyl]acetic acid (Ref: NOA 413163)

Minor fraction

Bayer verified

(E,E)-trifloxystrobin acid (Ref: CGA 321113)

Major fraction

0.970

Bayer verified

(E)-2-((((1-(3-(trifluoromethyl)phenyl)ethylidene)amino)oxy)methy)benzonitrile (Ref: CGA 357276)

Minor fraction

0.056

Bayer verified

methyl (2E)-(methoxyimino)[2-({[(Z)-{1-[3-(trifluoromethyl)phenyl]ethylidene}amino]oxy}methyl)phenyl]acetate (Ref: CGA 357261)

Minor fraction

Bayer verified

(2E)-(methoxyimino)[2-({[(Z)-{1-[3-(trifluoromethyl)phenyl]ethylidene}amino]oxy}methyl)phenyl]acetic acid (Ref: CGA 373466)

Minor fraction

Bayer verified

(2Z)-(methoxyimino)[2-({[(Z)-{1-[3-(trifluoromethyl)phenyl]ethylidene}amino]oxy}methyl)phenyl]acetic acid (Ref: CGA 381318)

Minor fraction

Bayer verified

2-({[(Z)-{1-[3-(trifluoromethyl)phenyl]ethylidene}amino]oxy}methyl)benzonitrile (Ref: NOA 409480)

Minor fraction

Bayer verified

(2Z)-[({2-[(E)-carboxy(methoxyimino)methyl]benzyl}oxy)imino][3-(trifluoromethyl)phenyl]acetic acid (Ref: NOA 413161)

Minor fraction

0.053

Bayer verified

Known groundwater metabolites

Metabolite

EC SANCO/221/2000 relevancy

ADI (mg kg⁻¹ bodyweight day⁻¹)

WHO drinking water guidance value (μg L⁻¹ day⁻¹)

(E,E)-trifloxystrobin acid (Ref: CGA 321113)

Relevant

0.01

(2Z)-[({2-[(E)-carboxy(methoxyimino)methyl]benzyl}oxy)imino][3-(trifluoromethyl)phenyl]acetic acid (Ref: NOA 413161)

Relevant

0.15

900

(2E)-[({2-[(E)-carboxy(methoxyimino)methyl]benzyl}oxy)imino][3-(trifluoromethyl)phenyl]acetic acid (Ref: NOA 413163)

Relevant

0.52

3120

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

(2Z)-[({2-[(E)-carboxy(methoxyimino)methyl]benzyl}oxy)imino][3-(trifluoromethyl)phenyl]acetic acid (Ref: NOA 413161)
Note: LD50(oral, rat) >2000 mg/kg; Risk to Groundwater

Plant

(2E)-[({2-[(E)-carboxy(methoxyimino)methyl]benzyl}oxy)imino][3-(trifluoromethyl)phenyl]acetic acid (Ref: NOA 413163)
Note: LD50(oral, rat) >2000 mg/kg

Plant

Ref: CGA 357261
Note: LD50(oral, rat) >2000 mg/kg; Koc = 389–567

Plant; Water (Photolysis)

Ref: NOA 414412
Note: LD50(oral, rat) >2000 mg/kg

Ref: CGA 166988

Poultry

Ref: NOA 417076

Poultry; Plant

methyl (2Z)-(methoxyimino)[2-({[(E)-{1-[3-(trifluoromethyl)phenyl]ethylidene}amino]oxy}methyl)phenyl]acetate (Ref: CGA 331409)

Plant; Water (Aerobic)

Ref: CGA 357362

Water (Photolysis)

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

> 6.4

Rat

High

(ppm diet)

> 100

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

> 73

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5200 mg kg feed⁻¹

Anas platyrhynchos

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

Colinus virginianus NOEL

Moderate

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

> 500

Eisenia foetida corr

Moderate

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

3.5

Eisenia foetida corr

Moderate

Soil micro-organisms

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

Dose: 0.27 mg kg⁻¹ soil 28 Day

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

249

Folsomia candida corr

Non-target plants

> 270

Brassica oleracea Daucus carota Lactuca sativa Zea mays Lolium perenne
Vegetative vigour, ER₅₀
as g ha⁻¹

> 270

Brassica oleracea Daucus carota Lactuca sativa Zea mays Lolium perenne
Seedling emergence, ER₅₀
as g ha⁻¹

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)

> 200

Apis mellifera

Low

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

Chronic as 10-day LC₅₀ µg bee⁻¹ day⁻¹

> 4.9

Apis mellifera

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) as Mortality LR₅₀ g ha⁻¹

> 500

Coccinella septempunctata

Beneficial insects (Lacewings) as Mortality LR₅₀ g ha⁻¹

> 383

chrysoperla carnea

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

> 500

Aphidius colemani

Beneficial insects (Predatory mites) as Mortality LR₅₀ g ha⁻¹

> 383

Typhlodromus pyri

Beneficial insects (Ground beetles) as Mortality LR₅₀ g ha⁻¹

> 500

Poecilus cupreus

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

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

0.022

Oncorhynchus mykiss

High

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

0.008

Oncorhynchus mykiss

High

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

> 0.052

Danio rerio Embryo

High

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

0.011

Daphnia magna

High

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

0.003

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)

0.45

Chironomus riparius EC₅₀

Moderate

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

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

0.2

Chironomus riparius

Moderate

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

1.93

Lemna gibba

Moderate

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

0.0053

Scenedesmus subspicatus

High

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

0.01

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)

> 2000

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.5

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.1

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

0.5

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

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

0.06

Dermal penetration studies (%)

1.6-3.8

concentration 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

Great Britain

GB MRL Register

Notes

Changes to sugarbeet GB MRL implemented April 2024

Drinking Water Standards

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

Respiratory tract irritant

Skin irritant

Skin sensitiser

Eye irritant

Phototoxicant

General human health issues

Probable liver & teste toxicant

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Hazard Class 9
Not expected to auto-ignite; Not highly flammable

CLP classification 2013

Health: H317
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

trifloxystrobin

French

trifloxystrobine

German

Trifloxystrobin

Danish

trifloxystrobin

Italian

trifloxistrobina

Spanish

trifloxiestrobina

Greek

Polish

trifloksystrobina

Swedish

trifloxystrobin

Hungarian

trifloxistrobin

Dutch

trifloxystrobine

Norwegian

trifloksystrobin

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