Ethirimol (Ref: PP149)

Ethirimol (Ref: PP149)	Last updated: 19/01/2021
(Also known as: ethyrimol)

GENERAL INFORMATION

Description

A pyrimidine fungicide often used as a seed treatment for diseaases. Can also be a pesticide transformation product

Example pests controlled

Damping-off; Powdery mildew

Example applications

Cereals including barley, wheat

Efficacy & activity

Availability status

Obsolete

Introduction & key dates

1968, first reported; 1970, first marketed

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

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

None

Chemical formula

C₁₁H₁₉N₃O

Canonical SMILES

CCCCC1=C(NC(=NC1=O)NCC)C

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

BBXXLROWFHWFQY-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C11H19N3O/c1-4-6-7-9-8(3)13-11(12-5-2)14-10(9)15/h4-7H2,1-3H3,(H2,12,13,14,15)

2D structure diagram/image available?

Yes

General status

Pesticide type

Fungicide, Metabolite

Metabolite Type

Soil

Substance group

Pyrimidinol

Minimum active substance purity

>97%

Known relevant impurities

Substance origin

Synthetic

Mode of action

Systemic, absorbed by roots and translocated. Inhibits nucleic acid synthesis (adenosine deaminase).

CAS RN

23947-60-6

EC number

245-949-3

CIPAC number

242

US EPA chemical code

228900

PubChem CID

32152

Molecular mass

209.29

PIN (Preferred Identification Name)

5-butyl-2-(ethylamino)-6-methylpyrimidin-4-ol

IUPAC name

5-butyl-2-ethylamino-6-methylpyrimidin-4-ol

CAS name

5-butyl-2-(ethylamino)-6-methyl-4(1H)-pyrimidinone

Other status information

PAN listed Highly Hazardous Chemical

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

Colourless crystals

Can be a metabolite of:

Parent

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

bupirimate

Soil

0.412

Major fraction, Relevant

Formulations

Property

Value

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

Milcurb Super
Milgo
Ferrax
Milcap

Example products using this active

Zeneca
Syngenta
ICI Plant Protection

Formulation and application details

Available in a variety of formulations including emulsifiable concentrates and soluble concentrates

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

233

Moderate

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

Melting point (°C)

159

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

2.00 X 10⁰²

Calculated

Log P

2.3

Low

Bulk density (g ml⁻¹)

1.21

Dissociation constant pKa) at 25 °C

Weak base

Vapour pressure at 20 °C (mPa)

0.267

Low volatility

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

2.00 X 10^-04

Non-volatile

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

Surface tension (mN m⁻¹)

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Moderately persistent

DT₅₀ (lab at 20 °C)

Moderately persistent

DT₅₀ (field)

Non-persistent

DT₉₀ (lab at 20 °C)

177

Persistent

DT₉₀ (field)

DT₅₀ modelling endpoint

Note

EU dosssier (for bupirimate) lab studies DT₅₀ range 19-114 days, DT₉₀ range 63-379 days; field studies DT₅₀ range 13-39 daysT

Dissipation rate RL₅₀ on plant matrix

Value

Note

Dissipation rate RL₅₀ on and in plant matrix

Value

3.5

Note

Cucumber fruit, undercover, n=1

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Note

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

Value

Moderately persistent

Note

Water-sediment DT₅₀ (days)

Water phase only DT₅₀ (days)

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

10.0

Moderately mobile

K_foc

402

¹/_n

0.849

Notes and range

EU dossier (for bupirimate) K_f range 1.8-33.0 mL g⁻¹, kfoc range 97-950 mL g⁻¹, ¹/_n range 0.808-0.883, Soils=4

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

1.82

Calculated

Transition state

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

Value

5.09 X 10^-02

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

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)

> 4000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat 2 year

(ppm diet)

> 200

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

Birds - Acute LD₅₀ (mg kg⁻¹)

> 3000

Perdix perdix

Low

Birds - Short term dietary (LC₅₀/LD₅₀)

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

60.8

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

>= 41.4

Oncorhynchus mykiss

Low

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

50.0

Daphnia magna

Moderate

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

7.3

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)

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)

Pseudokirchneriella subcapitata

Low

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)

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

1.6

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)

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

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

81.0

Folsomia candida 28d

Other arthropod (1)

LR₅₀ g ha⁻¹

% Effect

Harmless

Typhlodromus pyri

Other arthropod (2)

LR₅₀ g ha⁻¹

% Effect

Soil micro-organisms

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)

> 4000

Rat

Low

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

4.9

Rat

Other Mammal toxicity endpoints

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

0.05

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

0.05

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)

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

Exposure Routes

Public

Occupational

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

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

No further information available

Handling issues

Property

Value and interpretation

General

No information available

CLP classification 2013

Health: H312

EC Risk Classification

Xn - Harmful: R21

EC Safety Classification

S2, S36/37

WHO Classification

U/O (Obsolete substance / Unlikely to present an acute hazard)

UN Number

Waste disposal & packaging

TRANSLATIONS

Language

Name

English

ethirimol

French

ethyrimol

German

Ethirimol

Danish

ethirimol

Italian

etirimol

Spanish

etirimol

Greek

ethirimol

Polish

etyrymol

Swedish

Hungarian

Dutch

ethirimol

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