(Also known as: (+)-thujone; (+)-beta-thujone; 3-isothujone)
SUMMARY
Hazard alerts
The following Pesticide Hazard Tricolour (PHT) alerts are based on the data in the tables below. An absence of an alert does not imply the substance has no implications for human health, biodiversity or the environment but just that we do not have the data to form a judgement. The alerts for Highly Hazardous Pesticides (HHPs) are based on applying the FAO/WHO (Type 1) and the PAN (Type II) criteria to PPDB data. Further details on the HHP indicators are given in the tables below. Neither the PHT nor the HHP hazard alerts take account of usage patterns or exposure, thus they do not represent risk.
PHT: Environmental fate
PHT: Ecotoxicity
PHT: Human health
Highly Hazardous Pesticide
Human health High alert: Acetyl cholinesterase inhibitor; Neurotoxicant
GENERAL INFORMATION
Description
A botanical substance, common in some plant essential oils and which exhibits insecticidal activity
Example pests controlled
Red fire ant (Solenopsis invicta); Aphids, particularly the peach-potato aphid (Myzus persicae); Caribbean fruit fly (Anastrepha suspensa); Mediterranean fruit fly (Ceratitis capitata); Weevils; Various beetles
Example applications
Potatoes; Tomatoes; Vegetables; Stored produce
Efficacy & activity
-
GB regulatory status
GB COPR regulatory status
Not approved
Date COPR inclusion expires
Not applicable
GB LERAP status
No UK approval for use as a pest management agent
EC Regulation 1107/2009 (repealing 91/414)
EC Regulation 1107/2009 status
Not approved
Dossier rapporteur/co-rapporteur
Not applicable
Date EC 1107/2009 inclusion expires
Not applicable
EU Candidate for substitution (CfS)
Not applicable
Listed in EU database
No
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
Approved for use (✓) under EC 1107/2009 by Mutual Recognition of Authorisation and/or national regulations in the following EEA countries
ISIceland
NONorway
Additional information
Also used in
-
Chemical structure
Isomerism
Beta-thujone is one of the two diastereoisomeric forms of the bicyclic monoterpene ketone thujone, naturally occurring as the (+)-beta-thujone enantiomer. It differs from its more toxic counterpart, alpha-thujone, specifically in the stereochemical configuration at the C-4 position, where the methyl group is oriented differently relative to the thujane skeleton. Alpha-thujone is defined as the (1S, 4R, 5R) isomer and beta-thujone is the (1S, 4S, 5R) diastereomer. These isomers are not mirror images but share the same connectivity, with their distinct spatial arrangements resulting in different biological activities.
Acts as a non-competitive blocker of the GABA-A receptor, preventing the inhibitory neurotransmitter GABA from binding. This leads to the hyper-excitation of neurons, causing muscle spasms, convulsions, and eventually insect death. GABA Receptor Antagonism. Also an antifeedant.
Example manufacturers & suppliers of products using this active now or historically
Not produced specifically as a biopesticide
Example products using this active
-
Formulation and application details
-
Commercial production
Beta-thujone is not produced commercially through synthetic routes on a large scale due to its natural abundance and the availability of low-cost plant sources; instead, it is primarily obtained by isolation and purification from essential oils of plants rich in the beta-isomer, most notably cedar leaf oil from Thuja occidentalis (white cedar), where it often predominates or occurs in significant proportions alongside alpha-thujone. The process typically involves steam distillation of fresh or dried cedar leaves and branchlets to yield the crude essential oil, followed by chemical separation methods such as formation of crystalline bisulphite adducts to selectively isolate the ketone fraction (thujone isomers), hydrolysis or regeneration via hydrodistillation, and further purification by fractional distillation, chromatography, or other techniques to achieve high-purity beta-thujone. In some research or small-scale contexts, microbial transformations or chemical modifications (e.g., Beckmann rearrangement for derivatives) start from isolated beta-thujone, but commercial supply for fragrance, research, or biopesticide applications relies on natural extraction.
Impact on climate of production and use
Data for specific plant oils is scarce. However, from publicly available data the carbon footprint of plant oils has been estimated at between 1.0 and 4.0 kg CO₂e per kg of oil. This depends on the plant oil content, agricultural practices and processing methods used.
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C at pH 7 (mg l⁻¹)
407
Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source
at 25 °C
Moderate
Solubility - In organic solvents at 20 °C (mg l⁻¹)
-
-
-
Melting point (°C)
-
-
-
Boiling point (°C)
201
Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source
-
Degradation point (°C)
23
Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source
-
Flashpoint (°C)
-
-
-
Octanol-water partition coefficient at pH 7, 20 °C
P
4.90 X 1002
Calculated
-
Log P
2.69
Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source
Low
Fat solubility of residues
Solubility
-
-
-
Data type
-
-
-
Density (g ml⁻¹)
0.925
Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source
-
Dissociation constant pKa) at 25 °C
-
-
-
-
Vapour pressure at 20 °C (mPa)
-
-
-
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)
-
-
-
Degradation
Property
Value
Source; quality score; and other information
Interpretation
General biodegradability
Readily biodegradable
Soil degradation (days) (aerobic)
DT₅₀ (typical)
-
-
-
DT₅₀ (lab at 20 °C)
-
-
-
DT₅₀ (field)
-
-
-
DT₉₀ (lab at 20 °C)
-
-
-
DT₉₀ (field)
-
-
-
DT₅₀ modelling endpoint
-
-
-
Note
-
Dissipation rate RL₅₀ (days) on plant matrix
Value
-
-
-
Note
-
Dissipation rate RL₅₀ (days) on and in plant matrix
Value
-
-
-
Note
-
Aqueous photolysis DT₅₀ (days) at pH 7
Value
-
-
-
Note
-
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7
Value
-
-
-
Note
-
Water-sediment DT₅₀ (days)
-
-
-
Water phase only DT₅₀ (days)
-
-
-
Sediment 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)
-
-
-
Koc (mL g⁻¹)
-
Notes and range
-
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
-
-
-
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate
Value
Cannot be calculated
-
-
Note
-
Potential for particle bound transport index
-
-
-
Potential for loss via drain flow
-
-
-
Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk
-
-
-
Bio-concentration factor
BCF (l kg⁻¹)
25.9
Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source
Low potential
CT₅₀ (days)
-
-
Known soil and groundwater metabolites
None
Other known metabolites
Metabolite name and reference
Aliases
Formation medium / Rate
Estimated maximum occurrence fraction
-
7-hydroxy-beta-thujone
Humans
-
-
4-hydroxy-beta-thujone
Humans
-
ECOTOXICOLOGY
Terrestrial ecotoxicology
Property
Value
Source; quality score; and other information
Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
-
-
-
Mammals - Short Term Oral NOAEL (mg kg⁻¹ bw d⁻¹)
-
-
-
Mammals - Long Term (Chronic) Oral NOAEL (mg kg⁻¹ bw d⁻¹)
11
Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source
Note: These RTLs have been calculated using the regulatory approach used in the European Union and based on ecotoxocity values in the PPDB.
Species group
RTL
Notes
Mammals
2.2
Worst case of acute and chronic mammals
Birds
No data
No data for acute and chronic birds
Soil organisms
No data
No data for acute and chronic earthworms
Terrestrial plants
No data
No data for non-target plants vegetative vigour and seedling emergence
Pollinators
No data
No data for contact and oral honeybees
Arthropods
No data
No data for parasitic wasps and predatory mites
Fish
No data
No data for temperate acute and chronic fish
Aquatic invertebrates
No data
No data for temperate acute and chronic aquatic invertebrates
Aquatic plants
No data
No data for free-floating plants, rooted plants, acute and chronic algae
HUMAN HEALTH AND PROTECTION
General
Property
Value
Source; quality score; and other information
Interpretation
Threshold of Toxicological Concern (Cramer Class)
-
-
-
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
-
-
-
Mammals - Short Term Oral NOAEL (mg kg⁻¹ bw d⁻¹)
-
-
-
Mammals - Long Term (Chronic) Oral NOAEL (mg kg⁻¹ bw d⁻¹)
11
Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source
Rat NOAEL
Moderate
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
-
-
-
Mammals - Inhalation LC₅₀ (mg l⁻¹)
-
-
-
Other Mammal toxicity endpoints
Intraperitoneal LD₅₀ = 45.0 mg kg⁻¹
Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source
Mouse
-
Subcutaneous LD₅₀ = 442 mg kg⁻¹
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
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
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