Fenarimol (Ref: EL 222)

Fenarimol (Ref: EL 222)	Last updated: 19/01/2021
(Not known by any other names)

GENERAL INFORMATION

Description

A foliar fungicide used to control a range of diseases including powdery mildew, dollar spot and snow mould

Example pests controlled

Powdery mildew, Dollar spot, Snow mould, Scab, leaf spot, Rusts

Example applications

Fruit including bananas, chrry, filberts, grapes, pears; Ornamental plants and trees; Turf

Efficacy & activity

Availability status

Current

Introduction & key dates

1975, first reported; 1977, first introduced Lebanon

UK regulatory status

UK COPR regulatory status

Not approved

Date COPR inclusion expires

Expired

UK LERAP status

None

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Not approved

Dossier rapporteur/co-rapporteur

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

Australia, USA

Chemical structure

Isomerism

A chiral molecule existing in the R- and S-forms

Chemical formula

C₁₇H₁₂Cl₂N₂O

Canonical SMILES

C1=CC=C(C(=C1)C(C2=CC=C(C=C2)Cl)(C3=CN=CN=C3)O)Cl

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

NHOWDZOIZKMVAI-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C17H12Cl2N2O/c18-14-7-5-12(6-8-14)17(22,13-9-20-11-21-10-13)15-3-1-2-4-16(15)19/h1-11,22H

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
alpha-fenarimol	Isomer

General status

Pesticide type

Fungicide

Substance group

Pyrimidine

Minimum active substance purity

98%

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Systemic, curative and protective action. Disrupts membrane function.

CAS RN

60168-88-9

EC number

262-095-7

CIPAC number

380

US EPA chemical code

206600

PubChem CID

43226

Molecular mass

331.20

PIN (Preferred Identification Name)

rac-(R)-(2-chlorophenyl)(4-chlorophenyl)(pyrimidin-5-yl)methanol

IUPAC name

(RS)-2,4'-dichloro-a-(pyrimidin-5-yl)benzhydryl alcohol

CAS name

α-(2-chlorophenyl)-α-(4-chlorophenyl)-5-pyrimidinemethanol

Other status information

Chemical subject to PIC regulations

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

Off-white crystals

Formulations

Property

Value

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

Rimidin
Rubigan
Bloc

Example products using this active

AgriGuard
Rigby Taylor
Gowan
Elanco

Formulation and application details

Often supplied as a wettable powder or emulsifiable concentrate

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

13.7

Low

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

73300

Ethyl acetate

98000

Methanol

920

n-Heptane

33300

Xylene

Melting point (°C)

118

Boiling point (°C)

Degradation point (°C)

240

Flashpoint (°C)

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

4.90 X 10⁰³

Calculated

Log P

3.69

High

Bulk density (g ml⁻¹)

1.4

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

0.065

Low volatility

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

7.0 X 10^-04

Non-volatile

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

Neutral solution: 205.8nm = 33700
Acidic solution: 204.8nm = 35900
Basic solution: 221nm = 19000

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

250

Persistent

DT₅₀ (lab at 20 °C)

703

Very persistent

DT₅₀ (field)

Moderately persistent

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 436-1360 days, field studies DT₅₀ range 14-130 days; Other sources: range 60-130 days

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

7.8

Note

Grape berries, n=1

Aqueous photolysis DT₅₀ (days) at pH 7

Value

0.5

Fast

Note

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

Value

Stable

Note

Not sensitive to pH

Water-sediment DT₅₀ (days)

Stable

Water phase only DT₅₀ (days)

Moderately fast

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

6.7

Slightly mobile

K_foc

734

¹/_n

0.87

Notes and range

EU dossier kf range 1.5-11.9 mL g⁻¹, K_foc range 500-942 mL g⁻¹, ¹/_n range 0.86-0.90

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

2.12

Calculated

Transition state

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

Value

9.52 X 10^-02

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Slightly mobile

Calculated

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

fenarimol-N-oxide

Animal

2-chloro-2-(5-pyrimidyl)-4-chloro-benzophenone

Water (Photolysis)

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

113

Whole fish

Threshold for concern

CT₅₀ (days)

Not available

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

~ 2500

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

> 1.1

Rat 2 year

High

(ppm diet)

> 25

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 2000

Colinus virginianus

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

> 6250 mg kg feed⁻¹

Colinus virginianus

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

4.1

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.43

Oncorhynchus mykiss 69 day

Moderate

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

6.8

Daphnia magna

Moderate

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

0.113

Daphnia magna

Moderate

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

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

1.45

Chironomus riparius

Moderate

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

0.625

Chironomus riparius

Moderate

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

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

Non-target plants

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

1.48

Unknown species

Moderate

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

0.1

Unknown species

Moderate

Honeybees (Apis spp.)

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

> 100

Low

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

> 10

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)

> 250

Eisenia foetida

Moderate

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

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

100

Mortality [Dose: 32 g ha⁻¹]
Aphidius rhopalosiphi

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

Mortality [Dose: 32 g ha⁻¹]
Typhlodromus pyri protonymph

Soil micro-organisms

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

Dose: 7 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)

~ 2500

Rat

Low

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

2000

Rabbit

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 2.04

Rat

Other Mammal toxicity endpoints

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

0.01

Rat SF=100

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

0.02

Rat SF=100

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

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

0.02

Rat SF=100

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

Exposure Routes

Public

Acceptable level of risk for bystanders

Occupational

Acceptable level of risk for operators and other workers

MRLs

European

EU MRL pesticide database

Notes

Drinking Water Standards

Drinking Water MAC (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

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

May be fatal
May cause irritation or burns
Vapour may cause dizziness or suffocation
Endocrine issues - Antagonist of androgenic action

Handling issues

Property

Value and interpretation

General

Vapour may form explosive mixture with air
Highly flammable
IMDG Transport Code is usually 6.1

CLP classification 2013

Health: H361fd, H362
Environment: H411

EC Risk Classification

Reproduction risk category 3: R62, R63, R64
N - Dangerous for the environment: R51, R53

EC Safety Classification

S2, S36/37, S61

WHO Classification

III (Slightly hazardous)

UN Number

Usually 3017 or 3077

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

fenarimol

French

fenarimol

German

Fenarimol

Danish

fenarimol

Italian

fenarimol

Spanish

fenarimol

Greek

fenarimol

Polish

fenarimol

Swedish

Hungarian

fenarimol

Dutch

fenarimol

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