Fenamidone (Ref: RPA 407213)

Fenamidone (Ref: RPA 407213)	Last updated: 19/01/2021
(Not known by any other names)

GENERAL INFORMATION

Description

A fungicide effective against Oomycete diseases such as downy mildew and certain leaf spot diseases

Example pests controlled

Early and Late blight, Downy mildew, Alternaria leaf spot, Purple blotch

Example applications

Bulb vegetable crops; Potatoes; Tomatoes; Lettuce; Curcubits

Efficacy & activity

Availability status

Current

Introduction & key dates

1998, first reported; 2001, first registered

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

UK LERAP status

No UK approval for use

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

Czech Republic/France

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
			✓	✓	✓

Also used in

Chemical structure

Isomerism

A chiral molecule however only the S-isomer is biologically active and commercial products are stereospecific

Chemical formula

C₁₇H₁₇N₃OS

Canonical SMILES

CC1(C(=O)N(C(=N1)SC)NC2=CC=CC=C2)C3=CC=CC=C3

Isomeric SMILES

C[C@@]1(C(=O)N(C(=N1)SC)NC2=CC=CC=C2)C3=CC=CC=C3

International Chemical Identifier key (InChIKey)

LMVPQMGRYSRMIW-KRWDZBQOSA-N

International Chemical Identifier (InChI)

InChI=1S/C17H17N3OS/c1-17(13-9-5-3-6-10-13)15(21)20(16(18-17)22-2)19-14-11-7-4-8-12-14/h3-12,19H,1-2H3/t17-/m0/s1

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide

Substance group

Imidazole

Minimum active substance purity

975 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Protective and curative action. Respiration inhibitor (QoL fungicide).

CAS RN

161326-34-7

EC number

CIPAC number

650

US EPA chemical code

046679

PubChem CID

10403199

Molecular mass

311.40

PIN (Preferred Identification Name)

(5S)-3-anilino-5-methyl-2-(methylsulfanyl)-5-phenyl-3,5-dihydro-4H-imidazol-4-one

IUPAC name

(S)-1-anilino-4-methyl-2-methylthio-4-phenylimidazolin-5-one

CAS name

(5S)-3,5-dihydro-5-methyl-2-(methylthio)-5-phenyl-3-(phenylamino)-4H-imidazol-4-one

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 to cream fine powder

Related substances & organisms

propamocarb hydrochloride

Formulations

Property

Value

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

Consento
Reason

Example products using this active

Bayer CropScience

Formulation and application details

Often available as a soluble concentrate that is diluted 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)

7.8

Low

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

250000

Acetone

105700

Ethyl acetate

300

n-Heptane

43100

Methanol

Melting point (°C)

136.8

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

240

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

6.31 X 10⁰²

Calculated

Log P

2.8

Moderate

Bulk density (g ml⁻¹)

1.29

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C (mPa)

0.00034

Low volatility

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

5.00 X 10^-06

Non-volatile

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

Neutral pH: 202.5nm = 18470, 230 nm = 9148
Acidic pH; 203nm = 25138, 230nm=15734
Alkaline pH: 228.5 = 38838

Surface tension (mN m⁻¹)

72.9

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

6.9

Non-persistent

DT₅₀ (lab at 20 °C)

6.9

Non-persistent

DT₅₀ (field)

8.1

Non-persistent

DT₉₀ (lab at 20 °C)

30.0

Moderately persistent

DT₉₀ (field)

28.6

DT₅₀ modelling endpoint

Note

EU dossier (2016) Lab studies DT₅₀ range 0.5-20.9 days, DT₉₀ range 5.0-81.8 days, Soils=7; Field studies DT₅₀ range 4.6-51.2 days, DT₉₀ range 15.1-51.2 days

Dissipation rate RL₅₀ on plant matrix

Value

3.5

Note

Gherkin fruit, n=1

Dissipation rate RL₅₀ on and in plant matrix

Value

11.1

Note

Published literature RL₅₀ range 9.4-12.2 days, 3 field & undercover grown crops, various matrices, n=3

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Moderately fast

Note

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

Value

411

Very persistent

Note

pH sensitive: DT₅₀ 221 days at pH 5, 27.6 days at pH 9

Water-sediment DT₅₀ (days)

Moderately fast

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

5.1

Moderately mobile

K_foc

388

¹/_n

0.77

Notes and range

EU dossier K_f range 2.43-6.89 mL g⁻¹, K_foc range 259-494 mL g⁻¹, ¹/_n range 0.69-0.83, Soils=4

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.28

Calculated

Low leachability

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

Value

1.35 X 10^-02

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

(S)-5-methyl-5-phenylimidazolidine-2,4-dione (Ref: RPA 412636)

Soil

0.350

Major fraction, Relevant

(S)-5-methyl-2-methylthio-3-(2-nitrophenylamino)-5-phenyl-3,5-dihydroimidazol-4-one (Ref: RPA 413255)

Soil

0.131

Major fraction, Relevancy unknown

(S)-5-methyl-2-methylthio-5-phenyl-3,5-dihydroimidazol-4-one (Ref: RPA 412708)

Soil

0.172

Major fraction, Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

Ref: RPA 410193

(a) Plant; (b) Water (Photolysis)

b=0.134

Ref: RPA 409344

Water (Hydrolysis)

0.322

Ref: RPA 408056

Water (Photolysis)

0.356

Ref: RPA 221607

Soil

0.126

Ref: RPA 221701

Soil

0.115

Ref: RPA 411639

Soil

0.117

Ref: BCS-CV62706

Soil

0.082

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

Low risk

Based on LogP < 3

Low risk

CT₅₀ (days)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

2028

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat

High

(ppm diet)

500

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

328

Rat Reproductive NOAEL

Low

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 5200 ppm

Colinus virginianus

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

133

Colinius virginianus NOEL

Moderate

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

0.74

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.31

Oncorhynchus mykiss

Moderate

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

0.19

Daphnia magna

Moderate

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

0.0125

Daphnia magna

Moderate

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)

0.05

Chironomus riparius

Moderate

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

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

0.88

Lemna gibba

Moderate

Non-target plants

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

3.84

Raphidocelis subcapitata 72 hour

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)

> 25.7

Apis mellifera

Moderate

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

> 93.3

Apis mellifera

Moderate

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)

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 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)

> 25

Eisenia foetida

Moderate

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

0.315

Eisenia foetida corr

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

4.51

Folsomia candida

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

50 / 75

Mortality / Reproduction [Dose: 0.051 kg ha⁻¹]
Aphidius rhopalosiphi adult

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

4.5 / 16

Mortality / Reproduction [Dose: 0.051 kg ha⁻¹]
Typhlodromus pyri protonymph

Soil micro-organisms

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

Dose: 1.6 kg ha⁻¹

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)

2028

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 2.1

Rat 4 hrs (nose only)

Other Mammal toxicity endpoints

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

0.03

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

None allocated

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

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

0.3

Rat 90 day SF=100

Dermal penetration studies (%)

1.75-4.3

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Minimal risk of dietary exposure

Occupational

European MRLs

EU MRL pesticide database

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

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

General human health issues

Possible liver and thyroid toxicant

Handling issues

Property

Value and interpretation

General

Prevent generation of mists
Not explosive or oxidising
IMDG Transport Code is usually 9

CLP classification 2013

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

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

fenamidone

French

fenamidone

German

Fenamidone

Danish

fenamidon

Italian

fenamidone

Spanish

fenamidona

Greek

fenamidone

Polish

fenamidon

Swedish

Hungarian

fenamidon

Dutch

fenamidon

Record last updated:	19/01/2021
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