Bioallethrin	Last updated: 04/02/2024
(Also known as: allethrin; esbiol; esdeballethrin; esbiothrin)

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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	allethrin S-bioallethrin

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	-	-	-

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	-

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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