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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
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)
8
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
A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications )
5 = Verified data used for regulatory purposes
Moderate
Solubility - In organic solvents at 20 °C (mg l⁻¹)
- - -
Melting point (°C)
159
Q3 Q = Miscellaneous internet resources
3 = Unverified data of known source
-
Boiling point (°C)
Decomposes before boiling
V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM )
3 = Unverified data of known source
-
Degradation point (°C)
- - -
Flashpoint (°C)
Not expected to self ignite; Not highly flammable
V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM )
3 = Unverified data of known source
-
Octanol-water partition coefficient at pH 7, 20 °C
P
2.00 X 1002 Calculated -
Log P
2.3
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Low
Bulk density (g ml⁻¹)
1.21
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
-
Dissociation constant pKa) at 25 °C
5
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
-
Weak base
Vapour pressure at 20 °C (mPa)
0.267
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Low volatility
Henry's law constant at 25 °C (Pa m³ mol⁻¹)
2.00 X 10-04
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
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)
77
T4 T = UN EPFA database
4 = Verified data
Moderately persistent
DT₅₀ (lab at 20 °C)
53
A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications )
5 = Verified data used for regulatory purposes
Moderately persistent
DT₅₀ (field)
20
A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications )
5 = Verified data used for regulatory purposes
Non-persistent
DT₉₀ (lab at 20 °C)
177
A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications )
5 = Verified data used for regulatory purposes
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
R3 R = Peer reviewed scientific publications
3 = Unverified data of known source
-
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
30
A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications )
5 = Verified data used for regulatory purposes
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
Kd
- - -
Koc
-
Notes and range
-
Freundlich
Kf
10.0
A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications )
5 = Verified data used for regulatory purposes
Moderately mobile
Kfoc
402
1/n
0.849
Notes and range
EU dossier (for bupirimate) Kf 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
No
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
A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications )
5 = Verified data used for regulatory purposes
Based on LogP < 3
Low risk
CT₅₀ (days)
- -
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
> 4000
A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications )
5 = Verified data used for regulatory purposes
Rat
Low
Mammals - Short term dietary NOEL
(mg kg⁻¹)
-
L2 L = Pesticide manuals and hard copy reference books / other sources
2 = Unverified data of unknown source
Rat 2 year
-
(ppm diet)
> 200 -
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)
- - -
Birds - Acute LD₅₀ (mg kg⁻¹)
> 3000
A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications )
5 = Verified data used for regulatory purposes
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
A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications )
5 = Verified data used for regulatory purposes
Oncorhynchus mykiss
Moderate
Fish - Chronic 21 day NOEC (mg l⁻¹)
>= 41.4
A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications )
5 = Verified data used for regulatory purposes
Oncorhynchus mykiss
Low
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
50.0
A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications )
5 = Verified data used for regulatory purposes
Daphnia magna
Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)
7.3
A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications )
5 = Verified data used for regulatory purposes
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)
24
A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications )
5 = Verified data used for regulatory purposes
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
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
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
A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications )
5 = Verified data used for regulatory purposes
Folsomia candida 28d
-
Other arthropod (1)
LR₅₀ g ha⁻¹
- - -
% Effect
Harmless
AA2 AA = IOBC Database on classification of side effects to beneficial organisms, 2005
2 = Unverified data of unknown source
Typhlodromus pyri
-
Other arthropod (2)
LR₅₀ g ha⁻¹
- - -
% Effect
- - -
Soil micro-organisms
- - -
Mesocosm study data
NOEAEC mg l⁻¹
- - -
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
A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications )
5 = Verified data used for regulatory purposes
Rat
Low
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
2000
A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications )
5 = Verified data used for regulatory purposes
Rat
-
Mammals - Inhalation LC₅₀ (mg l⁻¹)
4.9
A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications )
5 = Verified data used for regulatory purposes
Rat
-
Other Mammal toxicity endpoints
- - -
ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)
0.05
A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications )
5 = Verified data used for regulatory purposes
-
ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)
0.05
A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications )
5 = Verified data used for regulatory purposes
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
XNo, known not to cause a problem
A3 A = Chromosome aberration (EFSA database)
3 = Negative
;
B0 B = DNA damage/repair (EFSA database)
0 = No data
;
C3 C = Gene mutation (EFSA database)
3 = Negative
;
D0 D = Genome mutation (EFSA database)
0 = No data
;
E0 E = Unspecified genotoxicity type (miscellaneous data source)
0 = No data
No data found
Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant
No data found
XNo, known not to cause a problem
XNo, known not to cause a problem
Respiratory tract irritant Skin irritant Skin sensitiser
No data found
XNo, known not to cause a problem
No data found
Eye irritant Phototoxicant  
Yes, known to cause a problem
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