Famoxadone (Ref: JE 874)

Famoxadone (Ref: JE 874)	Last updated: 31/10/2024
(Also known as: DPX JE874; IN JE874)

SUMMARY

Famoxadone is an oxazolidinedione fungicide. It has a low aqueous solubility, low risk of leaching to groundwater and is volatile. It is not persistent in soil or water. Whilst it has a low mammalian toxicity there is a slight concern regarding its ability to bioaccumulate. It is considered to be a neurotoxicant and is a known eye and skin irritant. It is highly toxic to fish and aquatic invertebrates and moderately toxic to other aquatic organisms, earthworms and honeybees.

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; Bees acute unknown ecotoxicity: High	Human health Moderate alert: Mammals chronic toxicity: Moderate; Genotoxic

GENERAL INFORMATION

Description

A fungicide used to control a broad spectrum of plant pathogenic fungi including downy mildew and blights

Example pests controlled

Alternaria Leaf Blight, Anthracnose, Downy Mildew, Phytophthora blight

Example applications

Potatoes; Tomatoes; Salad crops; Peppers; Cucurbits; Grapes; Spinach; Rocket

Efficacy & activity

Availability status

Current

Introduction & key dates

1996 first reported; 1998, first introduced

GB regulatory status

GB COPR regulatory status

Not approved

Date COPR inclusion expires

Withdrawn

GB LERAP status

Check label - may vary with formulation

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Finland

Date EC 1107/2009 inclusion expires

Not applicable

EU Candidate for substitution (CfS)

Yes - two 'Persistent-Bioaccumulative-Toxic' criteria

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

USA, Central and South America, South-east Asia, Africa, China, Japan

Chemical structure

Isomerism

A chiral molecule existing in the R- and S-forms. Substance is racemic (S-isomer to R-isomer ratio is about 1:1)

Chemical formula

C₂₂H₁₈N₂O₄

Canonical SMILES

CC1(C(=O)N(C(=O)O1)NC2=CC=CC=C2)C3=CC=C(C=C3)OC4=CC=CC=C4

Isomeric SMILES

International Chemical Identifier key (InChIKey)

PCCSBWNGDMYFCW-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C22H18N2O4/c1-22(16-12-14-19(15-13-16)27-18-10-6-3-7-11-18)20(25)24(21(26)28-22)23-17-8-4-2-5-9-17/h2-15,23H,1H3

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
S-famoxadone	S-isomer

General status

Pesticide type

Fungicide

Substance groups

Oxazole fungicide; Dicarboximide fungicide

Minimum active substance purity

960 g kg⁻¹

Known relevant impurities

EU dossier - 1,5-diphenylcarbonohydrazide at 0.0555 g kg⁻¹; 2-phenylacetohydrazide at 0.3 g kg⁻¹; phenylhydazine at 0.01 g kg⁻¹; benzene at 0.05 g kg⁻¹

Substance origin

Synthetic

Mode of action

Protectant with residual activity. Respiration inhibitor (QoL fungicide). Inhibits fungal mitochondrial respiration (at complex III), resulting in decreased ATP production. It is active against zoospore germination and mycelial growth.

CAS RN

131807-57-3

EC number

603-520-1

CIPAC number

594

US EPA chemical code

113202

PubChem CID

213032

CLP index number

612-206-00-3

Molecular mass

374.39

PIN (Preferred Identification Name)

rac-(5R)-3-anilino-5-methyl-5-(4-phenoxyphenyl)-1,3-oxazolidine-2,4-dione

IUPAC name

(RS)-3-anilino-5-methyl-5-(4-phenoxyphenyl)-1,3-oxazolidine-2,4-dione

CAS name

5-methyl-5-(4-phenoxyphenyl)-3-(phenylamino)-2,4-oxazolidinedione

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

Pale cream, odourless powder

Formulations

Property

Value

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

DuPont
Syngenta
Corteva Agriscience Australia Pty Ltd.

Example products using this active

Medley
Tanos
Famoxate
Equation Pro

Formulation and application details

Often formulated as an aqueous suspo-emulsion (SC)

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

0.059

Low

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

274000

Acetone

13300

Toluene

Hexane

125000

Ethyl acetate

Melting point (°C)

141.3

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

275

Flashpoint (°C)

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

4.47 X 10⁰⁴

Calculated

Log P

4.65

High

Fat solubility of residues

Solubility

Soluble

Data type

Regulatory data - observed in metabolism and farm animal feeding studies

Density (g ml⁻¹)

1.31

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

0.00064

Low volatility

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

4.06 X 10^-03

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

Negligible

From soil surface

Negligible

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

231nm = 553, shoulder at 275-280nm, no absorption after 290nm

Surface tension (mN m⁻¹)

73.0

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

41.1

Moderately persistent

DT₅₀ (lab at 20 °C)

41.1

Moderately persistent

DT₅₀ (field)

Non-persistent

DT₉₀ (lab at 20 °C)

152

Persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

2015 EU Dossier Lab studies DT₅₀ range 8.0-104.3 days, DT₉₀ range 27.5-214 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

12.3

Note

Grape berries, n=1

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

9.8

Note

Published literature RL₅₀ range 6.3-18.0 days, 5 field & undercover grown crops, various matrices, n=6

Aqueous photolysis DT₅₀ (days) at pH 7

Value

1.9

Moderately fast

Note

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

Value

Non-persistent

Note

pH sensitive: DT₅₀ 41 days at pH 5, 1.5 hours at pH 9 all at 25 °C

Water-sediment DT₅₀ (days)

0.7

Fast

Water phase only DT₅₀ (days)

0.1

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)

52.2

Slightly mobile

K_oc (mL g⁻¹)

3847

Notes and range

2015 EU dossier K_d range 23.4-89.1 mL g⁻¹, K_oc range 3307-4950 mL g⁻¹, soils=3

Freundlich

K_f (mL g⁻¹)

40.98

(2015 EU dossier)

Slightly mobile

K_foc (mL g⁻¹)

1455

¹/_n

0.832

Notes and range

EU 2015 dossier K_f range 4.5-127.0 mL g⁻¹, K_foc range 587-3414 mL g⁻¹, Soils=4

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.09

Calculated

Low leachability

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

Value

2.04 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

2.263

Calculated using the Atkinson method

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

3000

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

alpha-hydroxy-alpha-methyl-4-phenoxybenzene acetic acid (Ref: IN JS940)

Major fraction

0.111

5-[4-(4-hydroxyphenoxy)phenyl-5-methyl-3-(phenylamino)-2,4-oxazolidine dione (Ref: IN KZ007)

Major fraction

0.162

5-methyl-5-(4-phenoxyphenyl)-2,4-oxazolidinedione (Ref: IN-KF015)

Photolysis

(5RS)-5-methyl-3-[(2-nitrophenyl)amino]-5-(4-phenoxyphenyl)-1,3-oxazolidine-2,4-dione (Ref: IN-MN467)

Minor fraction

(5RS)-5-methyl-3-[(4-nitrophenyl)amino]-5-(4-phenoxyphenyl)-1,3-oxazolidine-2,4-dione (Ref: IN-MN468)

DT50 soil = 13.0 days; Kfoc=22482 mL/g

Known groundwater metabolites

None

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

formic acid (Ref: IN-02317)

Water (Photolysis)

1,2-benzenediol (Ref: IN-03492)

Hydrolysis; Water (Photolysis); Rat

4-aminophenyl acetate (Ref: IN-BY759)

Rat

4-aminophenyl (Ref: IN-CH490)

Animal

oxalic acid (Ref: IN-DI994)

Water (Photolysis)

benzenamine (Ref: IN-E0933)

Animal

3-aminophenol (Ref: IN-EK332)

Hen

5-methyl-5-(4-phenoxyphenyl)-2,4-oxazolidinedione (Ref: IN-KF015)

Water (Photolysis); Plant; Hen

potassium 2-phenylhydrazinecarboxylate (Ref: IN-KT983)

Hydrolysis

5-{4-)4-hydroxyphenoxy)phenyl]-5-methyl-2,4-oxazolidinedione (Ref: IN-ZK007)

Animal

3-[(4-hydroxyphenyl)amino]-5-methyl-5-(4-phenoxyphenyl)-2,4-oxazoldinediol (Ref: IN-KZ532)

Plant; Animal

5-[4-(4-hydroxyphenoxy)phenyl]-3-[(4-hydroxyphenyl)amino]-5-methyl-2,4-oxazolidinedione (Ref: IN-KZ534)

Plant; Animal

N-phyenylacetamide (Ref: IN-M0278)

Goat

Phenol (Ref: IN-M0371)

Hydrolysis; Water (Photolysis)

Ref: IN-ME338

Hen

alpha-hydroxy-4-(4-hydroxyphenoxy)-alpha-methyl-4- phenoxybenzeneaceticacid (Ref: IN-ML436)

Rat; Hen

alpha-hydroxy-4-(4-hydroxyphenoxy)-alpha-methylbenzeneacetic acid 2-phenylhydrazide (Ref: IN-LM815)

Plant; Animal

Ref: IN-MN967

Rat

Ref: IN-MP821

Plant; Hen

Ref: IN-MQ607

Goat

Ref: IN-MQ608

Hen

Ref: IN-MQ609

Hen

Ref: IN-MQ610

Hen

Ref: IN-MQ613

Plant

benzeneacetic acid (Ref: IN-JL856)

Water (Hydrolysis, Photolysis); Plant; Animal

1-(4-phenoxyphenyl_ethanone (Ref: IN-H3310)

Water (Hydrolysis); Water-Sediment systems; Plant; Animal

Ref: IN-MN968

Hydrolysis

4-phenoxybenzoic acid (Ref: IN-H3310)
Note: DT50 soil = 0.6 days; Kfoc=2157 mL/g

Water (Hydrolysis)

N-(4-hydroxyphenol)acetamide (Ref: IN-00915)

Animal

fumaric acid (Ref: IN-02162)

Water (Photolysis)

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)

3.3

Rat

High

(ppm diet)

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

> 44.7

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2250

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5620 mg kg feed⁻¹

Colinus virginianus

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

124.4

Colinus virginianus NOAEL

Moderate

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

235

Eisenia foetida corr

Moderate

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

8.15

Eisenia foetida corr

Moderate

Soil micro-organisms

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

Dose: 1.44 mg kg⁻¹ soil

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

> 300

Blackgrass Lambsquarter Chickweed Velvetleaf & others
Vegetative vigour, ER₅₀
as g ha⁻¹

> 201

Corn Onion Soybean Sugarbeet & others
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)

> 25

Apis mellifera

Moderate

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

> 1.0

Apis mellifera max conc due to solubility limit

Moderate

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

0.43

Apis mellifera 120 hr Larvae

High

Chronic

Notes

[The residual time to 25% mortality (RT25) value for honeybees is 1 hrs - USEPA data]

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

> 446

Coccinella septempunctata

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

> 446

Chrysoperla carnea/i>

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

> 2240

Aphidius rhopalosiphi

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

> 2240

Typhlodromus pyri

Beneficial insects (Ground beetles) as % Mortality at dose 700 g ha⁻¹

Poecilus cupreus

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

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

0.011

Oncorhynchus mykiss

High

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

0.0014

Oncorhynchus mykiss

High

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

1.24

Danio rerio

Moderate

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

0.033

Daphnia magna

High

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

0.0037

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)

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

> 0.007

Chironomus riparius

High

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

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

0.0081

Lemna gibba

High

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

0.00308

Pseudokirchneriella subcapitata

High

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)

> 5000

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 5.3

Rat 4 hr

Other Mammal toxicity endpoints

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

0.006

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

0.1

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

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

0.0024

Dermal penetration studies (%)

0.4-2.0

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

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

Occupational

Risk of exposure acceptable under label recommendations for use for personal protection clothing and equipment

MRLs

European

EU MRL pesticide database

Great Britain

GB MRL Register

Notes

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

; ; ; ;

No data found

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

Splene, liver & red blood cell toxicant
May cause long term eye damage from repeated exposure
Cataractogenic to dogs following repeat dose - human relevance cannot be ruled out

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
Not explected to auto-ignite, Not highly flammable
IMDG Transport Hazard Class 9

CLP classification 2013

Health: H373
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

Relatively unstable at ambient temperatures, Products should remain within specifications for at least 2 years when stored at ambient temperature

TRANSLATIONS

Language

Name

English

famoxadone

French

famoxadone

German

Famoxadone

Danish

famoxadon

Italian

famoxadone

Spanish

famoxadona

Greek

famoxadone

Polish

famoksadon

Swedish

famoxadon

Hungarian

famoxadon

Dutch

famoxadon

Norwegian

Record last updated:	31/10/2024
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