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Pyrethrins (cinerin I)
Last updated: 31/10/2024
(Also known as: pyrethum; cinerin)
GENERAL INFORMATION
Description
A non-persistent insecticide extracted from Pyrethrum used to control a variety of insect parasites
Availability status
Current
Introduction & key dates
circa 1930, introduced
Examples of veterinary uses
Used as a topical treatment for fleas and ticks as the pyrethrins mixture
Examples of species treated
Dogs; Cats; Horses
Approval status
VMR 2013/2033 approval status (GB/UK)
Not approved as cinerin I; Approved as pyrethrins (mix)
EU Regulatory approval status
Not approved as cinerin I; Approved as pyrethrins (mix)
Chemical structure
Isomerism
Cinerin-I is a complex molecule with three chiral centres.
Chemical formula
C₂₀H₂₈O₃
Canonical SMILES
CC=CCC1=C(C(CC1=O)OC(=O)C2C(C2(C)C)C=C(C)C)C
Isomeric SMILES
C/C=C\CC1=C([C@@H](CC1=O)OC(=O)[C@@H]2[C@H](C2(C)C)C=C(C)C)C
International Chemical Identifier key (InChIKey)
FMTFEIJHMMQUJI-RWRPJIPASA-N
International Chemical Identifier (InChI)
InChI=1S/C20H28O3/c1-7-8-9-14-13(4)17(11-16(14)21)23-19(22)18-15(10-12(2)3)20(18,5)6/h7-8,10,15,17-18H,9,11H2,1-6H3/b8-7-/t15-,17-,18+/m1/s1
2D structure diagram/image available?
Yes
General status
Veterinary substance type
Insecticide, Antiparasitic
Substance groups
Plant-derived substance
Minimum active substance purity
-
Known relevant impurities
-
Substance origin
Natural
Mode of action
Contact acting neurotoxins with repellent properties. Sodium channel modulator.
Molecular targets
-
CAS RN
25402-06-6
Alternative/old CAS RN
8003-34-7
EC number
246-948-0
CIPAC number
32
US EPA chemical code
-
PubChem CID
-
Therapeutic Class
Antiparasitic Products, Insecticides and Repellents: Ectoparasiticides, Insecticides and Repellents
ATCvet Code
QP53AC51
Controlled Drug?
No
Regulation 37/2010 MRL Classification
Allowed substance (Table 1: All food producing species)
Molecular mass
316.4
PIN (Preferred Identification Name)
-
IUPAC name
(Z)-(S)-3-(but-2-enyl)-2-methyl-4-oxocyclopent-2-enyl(1R)-trans-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate
CAS name
(1R-(1α(S(Z),3β))-3-(2-butenyl)-2-methyl-4-oxo-2-cyclopenten-1-yl 2,2-dimethyl-3-(2-methyl-1-propenyl) cyclopropanecarboxylate
Other status information
-
Relevant Environmental Water Quality Standards
-
Physical state
Viscous amber coloured liquid
Related substances & organisms
Formulations
Property
Product
Manufacturer
Authorisation Route
Legal Class (GB/UK)
Example products (past and present) using this active
- - - -
Formulation and application details
-
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
- - -
Solubility - In organic solvents at 20 °C (mg l⁻¹)
250000
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
n-Heptane		 -
250000
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
p-Xylene		 -
250000
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
Methane		 -
250000
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
Acetone		 -
Melting point (°C)
- - -
Boiling point (°C)
- - -
Degradation point (°C)
190
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
 -
Flashpoint (°C)
- - -
Octanol-water partition coefficient at pH 7, 20 °C
P
3.47 X 1005 Calculated -
Log P
5.54
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
 High
Fat solubility of residues
Solubility
- - -
Data type
- - -
Density (g ml⁻¹)
0.85
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 -
Dissociation constant pKa) at 25 °C
Not applicable
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
 -
No dissociation
Vapour pressure at 20 °C (mPa)
6.93 X 10-02
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
 Low volatility
Henry's law constant at 25 °C (Pa m³ mol⁻¹)
- - -
Volatilisation as max % of applied dose lost
From plant surface
- - -
From soil surface
- - -
Maximum UV-vis absorption L mol⁻¹ cm⁻¹
- - -
Surface tension (mN m⁻¹)
52.8
A4 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 )
4 = Verified data
as pyrethrins		 -
Refractive Index
- - -
Environmental release
-
Degradation
Property
Value
Source; quality score; and other information
Interpretation
Soil degradation (days) (aerobic)
DT₅₀ (typical)
2
A4 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 )
4 = Verified data
 Non-persistent
DT₅₀ (lab at 20 °C)
2.5
A4 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 )
4 = Verified data
 Non-persistent
DT₅₀ (field)
12
H4 H = The US ARS pesticide properties database. Dataset is no longer available.
4 = Verified data
 Non-persistent
DT₉₀ (lab at 20 °C)
6.3
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
 Non-persistent
DT₉₀ (field)
- - -
Note
EU dossier lab studies for pyrethrins
Manure DT₅₀ (days)
- - -
Aqueous photolysis DT₅₀ (days) at pH 7
Value
0.5
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
 Fast
Note
Rapid
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7
Value
528
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
 Very persistent
Note
-
Water-sediment DT₅₀ (days)
3.7
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
 Fast
Water phase only DT₅₀ (days)
1.0
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 fast
Air degradation
As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below.
Decay in stored produce DT₅₀
-
Soil adsorption and mobility
Property
Value
Source; quality score; and other information
Interpretation
Linear
Kd (mL g⁻¹)
-
H3 H = The US ARS pesticide properties database. Dataset is no longer available.
3 = Unverified data of known source
 Non-mobile
Koc (mL g⁻¹)
100000
Notes and range
Literature data
Freundlich
Kf (mL g⁻¹)
298
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-mobile
Kfoc (mL g⁻¹)
27019
1/n
0.986
Notes and range
EU dossier data for pyrethrins Kf range 198-430 mL g⁻¹, kfoc range 12472-74175 mL g⁻¹, 1/n range 0.907-1.10, Soils=4
pH sensitivity
No
Fate indices
Property
Value
Source; quality score; and other information
Interpretation
GUS leaching potential index
-0.47 Calculated Low leachability
Bio-concentration factor
BCF (l kg⁻¹)
471
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
Whole fish		 Threshold for concern
CT₅₀ (days)
Not available -
Known soil metabolites
Metabolite
Major/Minor fraction
Estimated maximum occurrence fraction
Notes
chrysanthemic acid
Minor fraction 0.05 -
Known groundwater metabolites

None

Other known metabolites
Metabolite name and reference
Aliases
Formation medium / Rate
Estimated maximum occurrence fraction
hydroxy-chrysanthenic acid - Plant -
dihydroxy-chrysanthenic acid - Plant -
dicarboxylic-chrysanthenic acid - Plant; Humans (Urine) -
aldehyde-chrysanthenic acid - Plant -
ECOTOXICOLOGY
Terrestrial ecotoxicology
Property
Value
Source; quality score; and other information
Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
1050
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
Rat		 Moderate
Mammals - Short term dietary NOEL
(mg kg⁻¹)
- - -
(ppm diet)
- -
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)
- - -
Birds - Acute LD₅₀ (mg kg⁻¹)
> 51151
A4 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 )
4 = Verified data
Anas platyrhynchos as pyrethrins		 Low
Birds - Short term dietary (LC₅₀/LD₅₀)
- - -
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)
- - -
Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)
23.7
A4 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 )
4 = Verified data
Eisenia foetida corr		 Moderate
Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)
0.25
A4 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 )
4 = Verified data
Eisenia foetida corr		 Moderate
Soil micro-organisms
- - -
Collembola
Acute LC₅₀ (mg kg⁻¹)
- - -
Chronic NOEC (mg kg⁻¹)
- - -
Non-target plants
- - -
- - -
Honeybees (Apis spp.)
Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
0.013
A4 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 )
4 = Verified data
Apis mellifera		 High
Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
0.10
K3 K = Research datasets (e.g. Pandora, Demetra; these datasets no longer available). Norman Ecotoxicology database. (click here )
3 = Unverified data of known source
Apis mellifera		 High
Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
- - -
Chronic
- - -
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 bee species (1)
Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)
- - -
Mode of exposure
-
Other bee species (2)
Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)
- - -
Mode of exposure
-
Beneficial insects (Ladybirds)
- - -
Beneficial insects (Lacewings)
- - -
Beneficial insects (Parasitic wasps)
Harmful
Q2 Q = Miscellaneous data from online sources
2 = Unverified data of unknown source
Parasitic wasp		 -
Beneficial insects (Predatory mites)
Harmless
AA2 AA = IOBC Database on classification of side effects to beneficial organisms, 2005
2 = Unverified data of unknown source
Typhlodromus pyri		 -
Beneficial insects (Ground beetles)
- - -
Aquatic ecotoxicology
Property
Value
Source; quality score; and other information
Interpretation
Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
0.005
A4 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 )
4 = Verified data
Oncorhynchus mykiss as pyrethrins		 High
Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)
- - -
Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
- - -
Temperate Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
0.273
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
Temperate Freshwater Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)
- - -
Tropical Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
- - -
Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)
0.0014
A4 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 )
4 = Verified data
Americamysis bahia as pyrethrins		 High
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)
- - -
Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)
320
S1 S = Expert judgement
1 = Estimated data with little or no verification
Unknown species		 Low
Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)
- - -
Mesocosm study data
NOEAEC mg l⁻¹
- - -
NOEAEC mg l⁻¹
- - -
Marine bivalves – Acute EC₅₀ development (mg l⁻¹)
- - -
HUMAN HEALTH AND PROTECTION
General
Property
Value
Source; quality score; and other information
Interpretation
Threshold of Toxicological Concern (Cramer Class)
Intermediate (class II) - -
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
1050
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
Rat		 Moderate
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 as Pyrethrins		 -
Mammals - Inhalation LC₅₀ (mg l⁻¹)
3.4
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
Rat as Pyrethrins		 -
Other Mammal toxicity endpoints
Intraperitoneal LD₅₀ = 200 mg kg⁻¹
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
Rat Pyrethrins		 -
ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)
0.04
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		 -
ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)
0.2
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)
None allocated
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
 -
Dermal penetration studies (%)
10
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
default		 -
Dangerous Substances Directive 76/464
- - -
Exposure Routes
Public
-
Occupational
-
Mammalian dose elimination route and rate
Almost completely excreted within 72hrs
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
 -
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
;
C0 C = Gene mutation (EFSA database)
0 = No data
;
D0 D = Genome mutation (EFSA database)
0 = No data
;
E3 E = Unspecified genotoxicity type (miscellaneous data source)
3 = Negative
?Possibly, status not identified
Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant
?Possibly, status not identified
XNo, known not to cause a problem
 No data found
Respiratory tract irritant Skin irritant Skin sensitiser
?Possibly, status not identified
XNo, known not to cause a problem
 No data found
Eye irritant Phototoxicant  
XNo, known not to cause a problem
 No data found  
General human health issues
May cause dermatitis
May cause gastointestinal problems
Possible thyroid and liver toxicant
Handling issues
Property
Value and interpretation
General
Not explosive or oxidising
Not expected to auto-ignite; Not highly flammable
IMDG Transport Hazard Class 9
CLP classification 2013
Health: H332, H312, H302
Environment: H400, H410
WHO Classification
II (Moderately hazardous)
UN Number
UN3082
Waste disposal & packaging
Packaging Group III (minor danger)
Shelf-life, storage, stability and reactivity
-
TRANSLATIONS
Language
Name
English
pyrethrins (cinerin I)
French
pyrethrines
German
Pyrethrine
Danish
pyrethrin
Italian
piretrine
Spanish
piretrina
Greek
-
Polish
pyretryny
Swedish
pyretriner
Hungarian
-
Dutch
pyrethrinen
Norwegian
-
Record last updated: 31/10/2024
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