Frontalin	Last updated: 23/08/2025
(Also known as: Beetle aggregation pheromone; Douglas fir beetle aggregation pheromone)

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Hazard alerts

The following 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. These hazard alerts do not take account of usage patterns or exposure, thus do not represent risk.

Environmental fate	Ecotoxicity	Human health
	Ecotoxicity Low alert: Birds acute ecotoxicity: Low; Fish acute ecotoxicity: Low; Daphnia acute ecotoxicity: Low; Bees acute unknown ecotoxicity: Low; Earthworms acute ecotoxicity: Low	Human health Moderate alert: Mammals acute toxicity: Moderate

GENERAL INFORMATION

Description	A volatile substance used, often in mixtures with other compounds, as an attractant and lure for fir, spruce and pine beetles
Example pests controlled	Douglas fir bark beetle (Dendroctonus pseudotsuga); Southern pine beetle (Dendroctonus frontalis); Spruce neetle (Dendroctonus rufipennis)
Example applications	Fir; Pine; Spruce
Efficacy & activity	-
Appearance and life cycle	-
Taxonomic classification	-

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 plant protection 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

Known to be also used in the following countries	-

Chemical structure

Isomerism	Frontalin is a chiral molecule with two asymmetric centres.
Chemical formula	C₈H₁₄O₂
Canonical SMILES	CC12CCCC(O1)(OC2)C
Isomeric SMILES	C[C@@]12CCC[C@@](O1)(OC2)C
International Chemical Identifier key (InChIKey)	AZWKCIZRVUVZPX-JGVFFNPUSA-N
International Chemical Identifier (InChI)	InChI=1S/C8H14O2/c1-7-4-3-5-8(2,10-7)9-6-7/h3-6H2,1-2H3/t7-,8+/m0/s1
2D structure diagram/image available?	Yes

General status

Biopesticide type	Insecticide; Semiochemical
Substance groups	Pheromone
Minimum active substance purity	>95%
Known relevant impurities	-
Substance origin	Natural
Mode of action	Functions as an insect attractant - aggregation distruption
Substance source	One of several components isolated from the Douglas fir bark beetle (Dendroctonus pseudotsuga) and other Coleoptera beetles
Uses	Forestry
Target pests	Douglas fir bark beetle (Dendroctonus pseudotsuga); Southern pine beetle (Dendroctonus frontalis); Spruce neetle (Dendroctonus rufipennis)
Target host	Fir; Pine; Spruce
Farming system suitability	-
CAS RN	28401-39-0
EC number	-
CIPAC number	-
US EPA chemical code	121201
PubChem CID	-
Molecular mass	142.20
PIN (Preferred Identification Name)	-
IUPAC name	(1S,5R)-1,5-dimethyl-6,8-dioxabicyclo[3.2.1]octane
CAS name	(1S,5R)-1,5-dimethyl-6,8-dioxabicyclo[3.2.1]octane
Forever chemical	-
Other status information	-
Relevant Environmental Water Quality Standards	-
Herbicide Resistance Class (HRAC MoA class)	Not applicable
Herbicide Resistance Class (WSSA MoA class)	Not applicable
Insecticide Resistance Class (IRAC MoA class)	Not known
Fungicide Resistance Class (FRAC MOA class)	Not applicable
Examples of recorded resistance	-
Physical state	Colourless to pale yellow liquid
Related substances & organisms	alpha-pinene camphene exo-brevicomin

Commercial

Property	Value
Availability status	Current
Introduction & key dates	1969, report of first isolation
Example manufacturers & suppliers of products using this active now or historically	ChemTica Contech Forestry Distributing Cultivar agriculture
Example products using this active	Douglas Fir Beetle Tree Bait Mountain Pine Beetle Tree Bait
Formulation and application details	Usually supplied in slow release formulations and dispensers
Commercial production	Frontalin is commercially produced through a stereoselective chemical synthesis due to its complex chiral structure. The process typically begins with a chiral auxiliary, such as 8-phenylmenthol esterified with pyruvic acid, which guides the formation of the desired enantiomer. Key steps include Grignard additions, oxidation with pyridinium dichromate, and ozonolysis followed by reductive work-up using dimethyl sulphide to yield either (+)- or (–)-frontalin, depending on the sequence of reagents used. This synthetic route allows for precise control over stereochemistry, which is critical since bark beetles respond selectively to specific enantiomers.
Impact on climate of production and use	While exact CO₂e values are not published for specific pheromones, some general information is available. The PHERA reported that biotechnological production (e.g. yeast fermentation) of pheromones can reduce GHG emissions by up to 90% compared to traditional chemical synthesis and GHG emissions are typically in the 5 to 10 kg CO₂e per kg of pheromone produced. Other sources suggest that small scale pheromone synthesis typically has emissions in the range 1 – 3 kg CO₂e per kg of pheromone produced.

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)		-	-	-
Melting point (°C)		-	-	-
Boiling point (°C)		-	-	-
Degradation point (°C)		-	-	-
Flashpoint (°C)		-	-	-
Octanol-water partition coefficient at pH 7, 20 °C	P	-	-	-
	Log P	-	-	-
Fat solubility of residues	Solubility	-	-	-
	Data type	-	-	-
Density (g ml⁻¹)		-	-	-
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		-
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		-

Known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property		Value	Source; quality score; and other information	Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)		> 1000	Q3 Q = Miscellaneous data from online sources 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)		> 2500	Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source No adverse effects identified or expected.	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)		> 1000	Q2 Q = Miscellaneous data from online sources 2 = Unverified data of unknown source Expert judgement	Low
Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)		-	-	-
Soil micro-organisms		-	-	-
Collembola	Acute LC₅₀ (mg kg⁻¹)	-	-	-
	Chronic NOEC (mg kg⁻¹)	-	-	-
Non-target plants	Vegetative vigour ER₅₀ (g ha⁻¹)	-	-	-
	Seedling emergence ER₅₀ (g ha⁻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)	-	-	-
	Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)	> 100	Q2 Q = Miscellaneous data from online sources 2 = Unverified data of unknown source Expert judgement	Low
	Chronic	-	-	-
	Notes	-
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)		> 100	Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source No adverse effects identified or expected.	Low
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)		> 100	Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source No adverse effects identified or expected.	Low
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 (free-floating, fonds growth, fresh) - 7 day (mg l⁻¹)		-	-	-
Aquatic plants (rooted, growth rate, fresh) - 14 day (mg l⁻¹)		-	-	-
Algae - Acute (growth rate, fresh; mg l⁻¹)		-	-	-
Algae - Chronic (growth rate, fresh; 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)		High (class III)	-	-
Mammals - Acute oral LD₅₀ (mg kg⁻¹)		> 1000	Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source Rat	Moderate
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)		-	-	-
Mammals - Inhalation LC₅₀ (mg l⁻¹)		-	-	-
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 ; E3 E = Unspecified genotoxicity type (miscellaneous data source) 3 = Negative XNo, known not to cause a problem Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant XNo, known not to cause a problem XNo, known not to cause a problem XNo, known not to cause a problem Respiratory tract irritant Skin irritant Skin sensitiser XNo, known not to cause a problem 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		No adverse human health issues identified

Handling issues

Property	Value and interpretation
General	No information available
CLP classification 2013	-
WHO Classification	Not listed (Not listed)
UN Number	-
Waste disposal & packaging	-
Shelf-life, storage, stability and reactivity	-

TRANSLATIONS

Language	Name
English	frontalin
French	frontaline
German	-
Danish	-
Italian	-
Spanish	-
Greek	-
Polish	-
Swedish	-
Hungarian	-
Dutch	-
Norwegian	-

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Record last updated:	23/08/2025
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