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famoxadone (Ref: JE 874)
** DPX JE874 ** IN JE874 ** Translations

Environmental Fate - Ecotoxicology - Human Health - A to Z Index - Home

SUMMARY

Famoxadone is an oxazolidinedione fungicide that is approved for use in the EU. 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.

GENERAL INFORMATION Click here for an explantaion of the general chemical status information
for famoxadone

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

Efficacy & activity: -

Availability status: Current

Introduction & key dates: 1996 first reported; 1998, first introduced

EC Regulation 1107/2009 (repealing 91/414):
Status Approved
Dossier rapporteur/co-rapporteur UK/Finland
Date inclusion expires 30/06/2019
EU Candidate for substitution (CfS) Yes - two 'Persistent-Bioaccumulative-Toxic' criteria
Listed in EU database Yes

Approved for use () or known to be used () in the following European countries: Click to access a note on the approvals information on this site

AT

BE

BG

CY

CZ

DE

DK

EE

EL

ES

FI

FR

HR

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

Also used in: USA

Chemical structure: Click here for further information on the general chemical status information used on this site
Isomerism A chiral molecule existing in the R- and S-forms
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 No data
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
Structure diagram/image available? Yes

General status: Click here for further information on the general chemical status information used on this site
Pesticide type Fungicide
Substance group Oxazole
Minimum active substance purity 960 g/kg
Known relevant impurities EU dossier - 1,5-diphenylcarbonohydrazide @ 0.0555 g/kg; 2-phenylacetohydrazide @ 0.3 g/kg; phenylhydazine @ 0.01 g/kg; benzene @ 0.05 g/kg
Substance origin Synthetic
Mode of action Protectant with residual activity, interferes with plant respiratory system. Respiration inhibitor (QoL fungicide).
CAS RN 131807-57-3
EC number 200-835-2
CIPAC number 594
US EPA chemical code 113202
PubChem CID 213032
Molecular mass (g mol-1) 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 Classification (HRAC) Not applicable
Herbicide Resistance Classification (WSSA) Not applicable
Insecticide Resistance Classification (IRAC) Not applicable
Fungicide Resistance Classification (FRAC) 11
Examples of recorded resistance -
Physical state Pale cream powder
Related substances & organisms

Formulations:
Property Click here for information on the general product and branding information used on this site Value
Example manufacturers & suppliers of products using this active now or historically
  • DuPont
  • Syngenta
Example products using this active
  • Medley
  • Tanos
  • Famoxate
  • Equation Pro
UK LERAP status Buffer probably required in UK - see product label
Formulation and application details -


ENVIRONMENTAL FATE

for famoxadone

Property Click here for information on the parameters used to describe environmental fate on this site Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with fate data Interpretation Click here for information on the way in which we interpret environmental fate data
Solubility - In water at 20oC (mg l-1) 0.059 A5 Low
Solubility - In organic solvents at 20oC (mg l-1) 274000 A5 - Acetone -
13300 A5 - Toluene -
48 A5 - Hexane -
125000 A5 - Ethyl acetate -
Melting point (oC) 141.3 A5 -
Boiling point (oC) Decomposes before boiling A5 -
Degradation point (oC) 275 A5 -
Flashpoint (oC) Not expected to self ignite; Not highly flammable A5 -
Octanol-water partition coefficient at pH 7, 20oC P 4.47 X 1004 Calculated -
Log P 4.65 A5 High
Bulk density (g ml-1)/Specific gravity 1.31 A5 -
Dissociation constant (pKa) at 25oC Not applicable A5 -
Note: No dissociation
Vapour pressure at 20oC (mPa) 0.00064 A5 Low volatility
Henry's law constant at 25oC (Pa m3 mol-1) 4.06 X 10-03 A5 Non-volatile
GUS leaching potential index Click here for a note on the limitations of the GUS index 1.35 Calculated Low leachability
SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate Click here for a note on the limitations of the SCI-GROW index Value 3.19 X 10-02 Calculated -
Note -
Potential for particle bound transport index Click here for a note on the limitations of the potential for particle bound transport index - Calculated High
Maximum UV-vis absorption L mol-1 cm-1 231nm = 553, shoulder at 275-280nm, no absorption after 290nm A5 -
Surface tension (mN m-1) 73.0 A5 -

Degradation:
Property Click here for information on the parameters used to describe substance degradation Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with degradation data Interpretation Click here for information on the way in which we interpret substance degradation data
General biodegradability -
Soil degradation (days) (aerobic) DT50 (typical) 41.1 A5 Moderately persistent
DT50 (lab at 20oC) 41.1 A5 Moderately persistent
DT50 (field) 20 F4 Non-persistent
DT90 (lab at 20oC) 152 A5 -
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 on plant matrix Value 12.3 R3 -
Note Grape berries, n=1
Dissipation rate RL50 on and in plant matrix Value 10.0 R4 -
Note Published literature RL50 range 6.3-18.0 days, 4 field & undercover grown crops, various matrices, n=5
Aqueous photolysis DT50 (days) at pH 7 Value 1.9 A5 Moderately fast
Note -
Aqueous hydrolysis DT50 (days) at 20oC and pH 7 Value 2 A5 Non-persistent
Note pH sensitive: DT50 41 days at pH 5, 1.5 hours at pH 9 all at 25 deg C
Water-sediment DT50 (days) 0.7 A5 Fast
Water phase only DT50 (days) 0.1 A5 Fast

Soil adsorption and mobility:
Property Click here for information on the parameters used to describe substance adsorption and mobility Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with adsorption and mobility data Interpretation Click here for information on the way in which we interpret substance adsorption and mobility
Linear Kd 52.2 A5 Slightly mobile
Koc 3847
Notes and range 2015 EU dossier Kd range 23.4-89.1 mL/g, Koc range 3307-4950 mL/g, soils=3
Freundlich Kf 40.98 A5 (2015 EU dossier) Slightly mobile
Kfoc 1455
1/n 0.832
Notes and range 2015 EU dossier Kf range 4.5-127.0 mL/g, Kfoc range 587-3414 mL/g, Soils=4
pH sensitivity No

Key metabolites:
Metabolite Formation medium Estimated maximum occurrence fraction 1107/2009 relevancy Click here for further information on 1107/2009 relevancy
alpha-hydroxy-alpha-methyl-4-phenoxybenzene acetic acid (Ref: IN-JS940) This metabolite may cause environmental pollution, click here for further information Soil   0.278   Major fraction, Relevancy unknown
5-[4-(4-hydroxyphenoxy)phenyl-5-methyl-3-(phenylamino)-2,4-oxazolidine dione (Ref: IN-KZ007) This metabolite may cause environmental pollution, click here for further information Soil   0.162   Minor fraction, Relevancy unknown

Other known metabolites:
Metabolite name and reference Aliases Formation medium / Rate Estimated maximum occurrence fraction Metabolising enzymes
N-(4-hydroxyphenol)acetamide
(Ref: IN-00915)
- Animal - -
fumaric acid
(Ref: IN-02162)
- Water (Photolysis) - -
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 - -
1-(4-phenoxyphenyl_ethanone
(Ref: IN-H3310)
- Water (Hydrolysis); Water-Sediment systems; Plant; Animal - -
(Ref: IN-H3310)
Note: DT50 soil = 0.6 days; Kfoc=2157 mL/g
- Water (Hydrolysis) - -
benzeneacetic acid
(Ref: IN-JL856)
- Water (Hydrolysis, Photolysis); Plant; Animal - -
5-methyl-5-(4-phenoxyphenyl)-2,4-oxazolidinedione
(Ref: IN-KF015)
Note: DT50 soil = 0.7 days
- Water (Photolysis); Soil (Photolysis); Plant; Hen - -
potassium 2-phenylhydrazinecarboxylate
(Ref: IN-KT983)
- Hydrolysis - -
3-[(4-hydroxyphenyl)amino]-5-methyl-5-(4-phenoxyphenyl)-2,4-oxazoldinediol
(Ref: IN-KZ532)
- Plant; Animal - -
(Ref: IN-KZ534) - Plant; Animal - -
(Ref: IN-LM815) - Plant; Animal - -
N-phyenylacetamide
(Ref: IN-M0278)
- Goat - -
Phenol
(Ref: IN-M0371)
- Hydrolysis; Water (Photolysis) - -
(Ref: IN-ME338) - Hen - -
(Ref: IN-ML436) - Rat; Hen - -
(Ref: IN-MN467)
Note: DT50 soil =10.6 days; Kfoc=31320 mL/g
- Soil - -
(Ref: IN-MN468)
Note: DT50 soil = 13.0 days; Kfoc=22482 mL/g
- Soil - -
(Ref: IN-MN967) - Rat - -
(Ref: IN-MN968) - Hydrolysis - -
(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 - -
5-{4-)4-hydroxyphenoxy)phenyl]-5-methyl-2,4-oxazolidinedione
(Ref: IN-ZK007)
- Animal - -


ECOTOXICOLOGY

for famoxadone

Property Click here for information on the parameters used to describe substance ecotoxicology Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with ecotoxicology data Interpretation Click here for information on the way in which we interpret substance ecotoxicology
Bio-concentration factor BCF (l kg-1) 3000 A5 Threshold for concern
CT50 (days) Not available -
Mammals - Acute oral LD50 (mg kg-1) > 5000 A5 Rat Low
Mammals - Short term dietary NOEL (mg kg-1) 3.3 F4 Rat High
(ppm diet) - -
Birds - Acute LD50 (mg kg-1) > 2250 A5 Colinus virginianus Low
Birds - Short term dietary (LC50/LD50) > 5620 mg kg feed-1 A5 Colinus virginianus -
Fish - Acute 96 hour LC50 (mg l-1) 0.011 A5 Oncorhynchus mykiss High
Fish - Chronic 21 day NOEC (mg l-1) 0.0014 A5 Oncorhynchus mykiss High
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) 0.033 A5 Daphnia magna High
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) 0.0037 A5 Daphnia magna High
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 A5 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 A5 Lemna gibba High
Non-target plants > 300 A5 Blackgrass, Lambsquarter, Chickweed, Velvetleaf & others
Vegetative vigour, ER50
as g/ha
-
> 201 A5 Corn, Onion, Soybean, Sugarbeet & others
Seedling emergence, ER50
as g/ha
-
Algae - Acute 72 hour EC50, growth (mg l-1) 0.00308 A5 Pseudokirchneriella subcapitata High
Algae - Chronic 96 hour NOEC, growth (mg l-1) - - -
Honeybees Contact acute 48 hour LD50 (μg bee-1) > 25 A5 Moderate
Oral acute 48 hour LD50 (μg bee-1) > 1.0 A4 [Max conc due to solubility limit] Moderate
Unknown mode acute 48 hour LD50 (μg bee-1) - - -
Earthworms - Acute 14 day LC50 (mg kg-1) 235 A5 Eisenia foetida, corr Moderate
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) 8.15 A5 Eisenia foetida, corr Moderate
Other soil macro-organisms - e.g. Collembola LR50 / EC50 / NOEC / % Effect - - -
Other arthropod (1) LR50 g ha-1 2240 >
A5 Aphidius rhopalosiphi
-
% Effect 100 Mortality
Dose: 0.3 kg ha-1
A5 Aphidius rhopalosiphi, adult
-
Other arthropod (2) LR50 g ha-1 2240 >
A5 Typhlodromus pyri
-
% Effect 99 Mortality
Dose: 0.099 kg ha-1
A5 Typhlodromus pyri, protonymph
-
Soil micro-organisms Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect
A5
Dose: 1.44 mg kg-1 soil
-
Mesocosm study data NOEAEC mg l-1 - - -
NOEAEC mg l-1 - - -


HUMAN HEALTH AND PROTECTION

for famoxadone

General:
Property Click here for information on the parameters used to describe human health and protection issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with human health and protection data Interpretation Click here for information on the way in which we interpret human health and protection data
Threshold of Toxicological Concern (Cramer Class) Click here for a note on the limitations of the Cramer class High (class III) - -
Mammals - Acute oral LD50 (mg kg-1) > 5000 A5 Rat Low
Mammals - Dermal LD50 (mg kg-1 body weight) > 2000 A5 Rat -
Mammals - Inhalation LC50 (mg l-1) > 5.3 A5 Rat, 4 hr -
Other Mammal toxicity endpoints - -
ADI - Acceptable Daily Intake (mg kg-1bw day-1) 0.012 A5 Dog, SF=100 -
ARfD - Acute Reference Dose (mg kg-1bw day-1) 0.2 A5 Mouse, SF=100 -
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) - - -
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) 0.0048 A4 Dog, 1 year, SF=100 -
Dermal penetration studies (%) 0.4-2.0 A5 concentration dependent -
Dangerous Substances Directive 76/464 - - -
Exposure Limits - - -
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
European MRLs Click here for the EU MRL pesticide database
Drinking Water Standards - - -
Drinking Water MAC (μg l-1) - - -

Health issues:
Carcinogen Mutagen Endocrine disrupter Reproduction / development effects Cholinesterase inhibitor Neurotoxicant

-

-

Respiratory tract irritant Skin irritant Skin sensitiser Eye irritant Phototoxicant

-

-

-

General human health issues Splene, liver & red blood cell toxicant
May cause long term eye damage from repeated exposure

: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data found

Handling issues:
Property Click here for information on the parameters used to describe substance handling issues Value Source/Quality Score/Other Information Click here for information on the primary data sources used to populate this database with data on handling issues Interpretation Click here for information on the way in which we interpret data on handling issues
General Click here for a description of the International Maritime Dangerous Goods (IMDG) codes Not explosive or oxidising
CLP classification 2013 Health: H373
Environment: H400, H410
EC Risk Classification Click here to view information omn the EU risk phrases Xn - Harmful: R48/22
N - Dangerous for the environment: R50, R53
EC Safety Classification Click here to view information omn the EU safety phrases S2, S46, S60, S61
WHO Classification U - Unlikely to present an acute hazard
US EPA Classification (formulation) III - Caution - Slightly toxic
UN Number Usually 1648
Waste disposal & packaging Click here for a description of UN packaging marks Packaging Group II (medium danger)


TRANSLATIONS

for famoxadone

Language Name
English famoxadone
French famoxadone
German Famoxadone
Danish famoxadon
Italian famoxadone
Spanish famoxadona
Greek famoxadone
Slovenian famoksadon
Polish famoksadon
Swedish famoxadon
Hungarian famoxadon
Dutch famoxadon

Record last updated: Wednesday 31 October 2018
Contact: aeru@herts.ac.uk