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Bioallethrin
Last updated: 04/02/2024
(Also known as: allethrin; esbiol; esdeballethrin; esbiothrin)
SUMMARY
Bioallethrin is an insecticide. It has a low aqueous solubility, is volatile and would not normally be expected to leach to groundwater. It is moderately persistent in soil and, under certain conditions, could be persistent in water. It is moderately toxic to mammals, is an endocrine disrupter and an eye irritant. Bioallethrin is highly toxic to fish but less so to birds and honeybees.
GENERAL INFORMATION
Description
A pyrethroid ester insecticide used mainly in domestic situations
Availability status
Current
Introduction & key dates
1969, introduced
Examples of veterinary uses
-
Examples of species treated
-
Approval status
VMR 2013/2033 approval status (GB/UK)
-
EU Regulatory approval status
-
Chemical structure
Isomerism
A mixture of two allethrin stereoisomers (1R,trans;1R and 1R,trans;1S) in an approximate ratio of 1:1, where both isomers are active ingredients
Chemical formula
C₁₉H₂₆O₃
Canonical SMILES
CC1=C(C(=O)CC1OC(=O)C2C(C2(C)C)C=C(C)C)CC=C
Isomeric SMILES
-
International Chemical Identifier key (InChIKey)
ZCVAOQKBXKSDMS-AQYZNVCMSA-N
International Chemical Identifier (InChI)
InChI=1S/C19H26O3/c1-7-8-13-12(4)16(10-15(13)20)22-18(21)17-14(9-11(2)3)19(17,5)6/h7,9,14,16-17H,1,8,10H2,2-6H3
2D structure diagram/image available?
Yes
General status
Veterinary substance type
-
Substance groups
Pyrethroid ester insecticide
Minimum active substance purity
-
Known relevant impurities
-
Substance origin
Synthetic
Mode of action
Non-systemic, contact and stomach action with a rapid knock-down effect. Sodium channel modulator.
Molecular targets
-
CAS RN
260359-57-7
EC number
249-013-5
CIPAC number
203
US EPA chemical code
004003
PubChem CID
11442
CLP index number
006-025-00-3
Therapeutic Class
-
ATCvet Code
-
Controlled Drug?
-
Regulation 37/2010 MRL Classification
-
Molecular mass
302.41
PIN (Preferred Identification Name)
(1E)-2-methyl-4-oxo-3-(prop-2-en-1-yl)cyclopent-2-en-1-yl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate
IUPAC name
(RS)-3-allyl-2-methyl-4-oxocyclopent-2-enyl (1R)-trans-2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropanecarboxylate
CAS name
2-methyl-4-oxo-3-(2-propenyl)-2-cyclopenten-1-yl (1R,3R)-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate
Other status information
-
Relevant Environmental Water Quality Standards
-
Physical state
Orange viscous 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)
4.6
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 Low
Solubility - In organic solvents at 20 °C (mg l⁻¹)
Miscible
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Acetone		 -
Miscible
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Ethanol		 -
Miscible
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Toluene		 -
Miscible
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Hexane		 -
Melting point (°C)
Not applicable
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
 -
Boiling point (°C)
168
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 -
Degradation point (°C)
- - -
Flashpoint (°C)
87
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
(closed cup)		 -
Octanol-water partition coefficient at pH 7, 20 °C
P
4.79 X 1004 Calculated -
Log P
4.68
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 High
Fat solubility of residues
Solubility
- - -
Data type
- - -
Density (g ml⁻¹)
1.01
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 -
Dissociation constant pKa) at 25 °C
- - -
-
Vapour pressure at 20 °C (mPa)
43.9
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 Highly volatile. If applied directly to plants or soil, drift is a concern & mitigation is advisable
Henry's law constant at 25 °C (Pa m³ mol⁻¹)
2.89
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 Moderately volatile
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)
- - -
Refractive Index
- - -
Environmental release
-
Degradation
Property
Value
Source; quality score; and other information
Interpretation
Soil degradation (days) (aerobic)
DT₅₀ (typical)
32
L2 L = Pesticide manuals and hard copy reference books / other sources
2 = Unverified data of unknown source
 Moderately persistent
DT₅₀ (lab at 20 °C)
- - -
DT₅₀ (field)
- - -
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
Note
Best available data
Manure DT₅₀ (days)
- - -
Aqueous photolysis DT₅₀ (days) at pH 7
Value
-
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 -
Note
Degraded by UV light
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7
Value
Stable
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 Stable
Note
Stable at pH 5 to pH 7: DT₅₀ 4.3 days at pH 9
Water-sediment DT₅₀ (days)
- - -
Water phase only DT₅₀ (days)
- - -
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)
-
V1 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
1 = Estimated data with little or no verification
 Non-mobile
Koc (mL g⁻¹)
9500
Notes and range
Estimated
Freundlich
Kf (mL g⁻¹)
- - -
Kfoc (mL g⁻¹)
-
1/n
-
Notes and range
-
pH sensitivity
-
Fate indices
Property
Value
Source; quality score; and other information
Interpretation
GUS leaching potential index
0.03 Calculated Low leachability
Bio-concentration factor
BCF (l kg⁻¹)
1897
F2 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
2 = Unverified data of unknown source
Estimated		 Threshold for concern
CT₅₀ (days)
Not available -
Known soil metabolites
Metabolite
Major/Minor fraction
Estimated maximum occurrence fraction
Notes
dihydroxyallethrolene
- - -
Known groundwater metabolites

None

Other known metabolites

None

ECOTOXICOLOGY
Terrestrial ecotoxicology
Property
Value
Source; quality score; and other information
Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
709
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat		 Moderate
Mammals - Short term dietary NOEL
(mg kg⁻¹)
-
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat		 -
(ppm diet)
750 -
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)
- - -
Birds - Acute LD₅₀ (mg kg⁻¹)
> 2030
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Colinus virginianus		 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)
- - -
Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)
- - -
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)
3.4
F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
4 = Verified data
Apis mellifera		 Moderate
Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)
6.85
R3 R = Peer reviewed scientific publications
3 = Unverified data of known source
Apis mellifera		 Moderate
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)
- - -
Beneficial insects (Predatory mites)
- - -
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)
0.024
F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
3 = Unverified data of known source
Lepomis macrochirus		 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)
0.0356
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Daphnia magna		 High
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)
- - -
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)
- - -
Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)
- - -
Mesocosm study data
NOEAEC mg l⁻¹
- - -
NOEAEC mg l⁻¹
- - -
Marine bivalves
- - -
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)
709
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat		 Moderate
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
3000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat		 -
Mammals - Inhalation LC₅₀ (mg l⁻¹)
2.5
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat		 -
Other Mammal toxicity endpoints
- - -
ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)
- - -
ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)
- - -
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
-
Mammalian dose elimination route and rate
- - -
Health issues
Specific human health issues
Carcinogen
Genotoxic
Endocrine disruptor
XNo, known not to cause a problem
A0 A = Chromosome aberration (EFSA database)
0 = No data
;
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
;
E0 E = Unspecified genotoxicity type (miscellaneous data source)
0 = No data
✓Yes, known to cause a problem
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
?Possibly, status not identified
?Possibly, status not identified
 No data found
Eye irritant Phototoxicant  
✓Yes, known to cause a problem
 No data found  
General human health issues
May cause lung congestion
US EPA - weak evidence to suggest possible human carcinogen
Endocrine issues - Inhibition of estrogen-sensitive cells proliferation
Handling issues
Property
Value and interpretation
General
No information available
CLP classification 2013
Health: H302, H332
Environment: H400, H410
WHO Classification
II (Moderately hazardous)
UN Number
-
Waste disposal & packaging
-
Shelf-life, storage, stability and reactivity
-
TRANSLATIONS
Language
Name
English
bioallethrin
French
bioallethrine
German
Bioallethrin
Danish
bioallethrin
Italian
bioalletrin
Spanish
bioalletrin; bioaletrina
Greek
bioallethrin
Polish
bioaletryna
Swedish
bioalletrin
Hungarian
-
Dutch
bioallethrin
Norwegian
-
Record last updated: 04/02/2024
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