Fluoxastrobin (Ref: HEC 5725)

Fluoxastrobin (Ref: HEC 5725)	Last updated: 28/01/2021
(Also known as: AE 1228646)

GENERAL INFORMATION

Description

A foliar applied, translaminar, systemic fungicide with preventative activity used for disease control on a wide range of vegetables

Example pests controlled

Early blight, Late blight, Leaf spots, Leaf rust, Rhizoctonia solani

Example applications

Vegetables; Turf; Peanuts; Potatoes; Onions; Cereals including wheat, rye, triticale, barley, oats

Efficacy & activity

Soybean/Blight=High; Soybean/Anthracnose=Moderate; Soybean/Brown spot=Moderate; Soybean/Leaf blight=Moderate. Data supported by field trials and extensive use.

Availability status

Current

Introduction & key dates

circa 2002

UK regulatory status

UK COPR regulatory status

Approved

Date COPR inclusion expires

31/07/2024

UK LERAP status

Buffer probably required in UK - see product label

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

UK/Czech Republic

Date EC 1107/2009 inclusion expires

31/07/2021

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

Chemical structure

Isomerism

Isomeric - exists in both E- and Z- forms

Chemical formula

C₂₁H₁₆ClFN₄O₅

Canonical SMILES

CON=C(C1=CC=CC=C1OC2=C(C(=NC=N2)OC3=CC=CC=C3Cl)F)C4=NOCCO4

Isomeric SMILES

CO/N=C(\C1=CC=CC=C1OC2=C(C(=NC=N2)OC3=CC=CC=C3Cl)F)/C4=NOCCO4

International Chemical Identifier key (InChIKey)

UFEODZBUAFNAEU-NLRVBDNBSA-N

International Chemical Identifier (InChI)

InChI=1S/C21H16ClFN4O5/c1-28-26-18(21-27-30-11-10-29-21)13-6-2-4-8-15(13)31-19-17(23)20(25-12-24-19)32-16-9-5-3-7-14(16)22/h2-9,12H,10-11H2,1H3/b26-18+

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
E-fluoxastrobin	E-isomer

General status

Pesticide type

Fungicide

Substance group

Strobilurin

Minimum active substance purity

940 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Systemic with protectant and curative properties. Respiration inhibitor (QoL fungicide).

CAS RN

361377-29-9

EC number

CIPAC number

746

US EPA chemical code

028869

PubChem CID

11048796

Molecular mass

458.83

PIN (Preferred Identification Name)

IUPAC name

(E)-{2-[6-(2-chlorophenoxy)-5-fluoropyrimidin-4-yloxy]phenyl}(5,6-dihydro-1,4,2-dioxazin-3-yl)methanone O-methyloxime

CAS name

(1E)-[2-[[6-(2-chlorophenoxy)-5-fluoro-4-pyrimidinyl]oxy]phenyl](5,6-dihydro-1,4,2-dioxazin-3-yl)methanone O-methyloxime

Other status information

Relevant Environmental Water Quality Standards

Herbicide Resistance Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Not applicable

Fungicide Resistance Classification (FRAC)

Examples of recorded resistance

Physical state

White crystalline solid

Related substances & organisms

prothioconazole

Formulations

Property

Value

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

Fandango
Jaunt

Example products using this active

Bayer CropScience
Clayton

Formulation and application details

Often supplied 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)

2.56

Low

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

n-Heptane

38000

Xylene

250000

Ethyl acetate

1100

n-Octanol

Melting point (°C)

103

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

230

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

7.24 X 10⁰²

Calculated

Log P

2.86

Moderate

Bulk density (g ml⁻¹)

1.42

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

5.60 X 10^-07

Low volatility

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

1.00 X 10^-07

Non-volatile

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

250nm = 19358, no absorbance above 290nm

Surface tension (mN m⁻¹)

68.1

at 20 °C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Not readily biodegradable

Soil degradation (days) (aerobic)

DT₅₀ (typical)

58.8

Moderately persistent

DT₅₀ (lab at 20 °C)

58.8

Moderately persistent

DT₅₀ (field)

52.6

Moderately persistent

DT₉₀ (lab at 20 °C)

202.2

Persistent

DT₉₀ (field)

335.4

DT₅₀ modelling endpoint

26.96

geometric mean of normalised values

Note

EU 2018 dossier lab studies DT₅₀ range 10.8-160.2 days, DT₉₀ range 49.1-532.1 days, Soils=4; Field studies: DT₅₀ range 11.5-91.7 days, DT₉₀ range 93.6-552.8 days, Soils=5

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

Note

Aqueous photolysis DT₅₀ (days) at pH 7

Value

33.4

Stable

Note

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

Value

Stable

Note

Stable pH 4 to pH 9

Water-sediment DT₅₀ (days)

163

Slow

Water phase only DT₅₀ (days)

Slow

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

14.7

Slightly mobile

K_foc

848

¹/_n

0.86

Notes and range

EU 2018 dossier K_f range 3.4-26.3 mL g⁻¹, K_foc range 424-1582 mL g⁻¹, ¹/_n range 0.84-0.87, Soils=4

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.84

Calculated

Transition state

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

Value

6.36 X 10^-02

Calculated

Note

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

HEC-5725-des-chlorophenyl (Ref: HEC 7155)

Soil

0.322

Major fraction, Relevant

HEC-5725-carboxylic acid (Ref: HEC 7180)

Soil

0.169

Major fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

2-chlorophenol

fluoxastrobin M82

Soil

HEC 5725-phenoxy-hydroxypyrimidine; fluoxastrobin M55

Animal

HEC 5725-2-chlorophenol-glucoside; fluoxastrobin M84

Plant

HEC 5725-oxazepine; fluoxastrobin M36

Water (Photolysis)

HEC5725-phenoxy-aminopyrimidine; fluoxastrobin M56

Water (Photolysis)

HEC 5725-ketone; fluoxastrobin M34

Plant

HEC 5725-carboxylic acid glycol ester; fluoxastrobin M39

Plant

HEC 5725-hydroxy carboxylic acid; fluoxastrobin M41

Plant

HEC 5725-OH-phenoxy-amino-PMD; fluoxastrobin M57

Plant

HEC 5725-des-chlorophenyl-glycol-MA; fluoxastrobin M70

Plant

HEC 5725-des-chlorophenyl-carboxylic acid; fluoxastrobin M72

Plant

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

52.1

Low potential

CT₅₀ (days)

0.4

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

> 1.5

Dog

High

(ppm diet)

> 100

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

> 764

Rat Reproductive NOAEL

Low

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 2000 mg kg bw⁻¹ day⁻¹

Colinus virginianus

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

Anas platyrhynchos NOAEL

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.435

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.0286

Oncorhynchus mykiss

Moderate

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

0.48

Daphnia magna

Moderate

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

0.18

Daphnia magna

Moderate

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

0.0604

Americamysis bahia

High

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

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

1.2

Chironomus riparius EC05 Development

Moderate

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

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

> 6

Lemna gibba

Moderate

Non-target plants

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

0.35

Pseudokirchneriella subcapitata

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

Apis mellifera

Low

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

> 843

Apis mellifera

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)

> 100

Bombus terrestris

Low

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

> 209

Bombus terrestris

Low

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)

Eisenia foetida corr

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

5.0

Folsomia candida corr

Other arthropod (1)

LR₅₀ g ha⁻¹

34.1

Mortality
Aphidius rhopalosiphi adult

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

122.2

Mortality
Typhlodromus pyri protonymph

% Effect

Soil micro-organisms

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

Dose: 2.83 mg kg⁻¹ soil

Mesocosm study data

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)

> 2000

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.0

Rat 4 hr (nose only)

Other Mammal toxicity endpoints

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

0.015

Dog SF=100

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

0.08

Dog SF=100

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

0.08

Dog SF=100

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

0.03

Dog 90 day SF=100

Dermal penetration studies (%)

4.0

Dangerous Substances Directive 76/464

List II

Exposure Routes

Public

Minimal risk from dietary exposure
Risk assessment indicates ARfD would not normally be execeeded

Occupational

MRLs

European

EU MRL pesticide database

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

0.1

EU Dir 89/778/EC limit; Calc MAC=45 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

Eye irritant

Phototoxicant

General human health issues

Possible liver & kidney toxicant

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Code is usually 9

CLP classification 2013

Health: H317
Environment: H400, H410

EC Risk Classification

N - Dangerous for the environment: R50, R53

EC Safety Classification

S60, S61

WHO Classification

NL (Not listed)

UN Number

Usually 3077

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

fluoxastrobin

French

fluoxastrobine

German

Fluoxastrobin

Danish

fluoxastrobin

Italian

fluoxastrobin

Spanish

fluoxastrobeno

Greek

Polish

fluoksastrobina

Swedish

Hungarian

Dutch

Record last updated:	28/01/2021
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