(Also known as: Straight Chain Lepidopteran Pheromone; SCLP; tetra-11-enyl acetate; Tea tortrix sex pheromone; Omnivorous leafroller pheromone; Sparganothris fruitworm pheromone)
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.
A volatile substance that is classed as a Straight Chain Lepidopteran Pheromone (SCLP) and used as an insect attractant
Example pests/issues controlled
Various insects belong to the Lepidoptera order including the codling moth (Cydia pomonella), European corn borer (Ostrinia nubilalis, pandemis leafroller (Pandemis pyrusana) and the fruit tree leafroller (Archips argyrospilus)
Example applications
Top fruit; Stone fruit; Tree nuts
Efficacy & activity
-
Appearance and life cycle
-
Taxonomic classification
-
GB regulatory status
GB COPR regulatory status
Approved
Date COPR inclusion expires
31/08/2029
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
Approved
Dossier rapporteur/co-rapporteur
Italy/France
Date EC 1107/2009 inclusion expires
30/08/2037
EU Candidate for substitution (CfS)
No
Listed in EU database
Yes
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
USA
Chemical structure
Isomerism
(E)-tetradec-11-enyl acetate exhibits geometric (cis/trans or E/Z) isomerism, due to the presence of a carbon–carbon double bond at the 11th position of its 14-carbon chain.
Example manufacturers & suppliers of products using this active now or historically
CBC Europe
Pacific Biocontrol Corp
Shin Etsu
Example products using this active
Formulation and application details
Usually supplied in slow release formulations & dispensers, or in solution for spray application
Commercial production
The synthesis of (E)-tetradec-11-enyl acetate begins with a suitable starting material, often a long-chain alkene or alkyne which undergoes hydroformylation, a process that adds a formyl group (CHO) to the carbon chain, resulting in an aldehyde intermediate. The aldehyde intermediate is then reduced to the corresponding alcohol using a reducing agent such as sodium borohydride or lithium aluminium hydride. The resulting alcohol is subjected to isomerisation to ensure the double bond is in the correct position (at the 11th carbon) and in the desired configuration (trans or E). Finally, the alcohol is acetylated to form the acetate ester, (E)-tetradec-11-enyl acetate. This step can be achieved using acetic anhydride or acetyl chloride in the presence of a catalyst. It is then purified.
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 at pH 7 (mg l⁻¹)
4.0
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
Low
Solubility - In organic solvents at 20 °C (mg l⁻¹)
Miscible
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
Toluene
-
Miscible
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
Ethyl ether
-
Miscible
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
benzene
-
Insoluble
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
DMSO
-
Melting point (°C)
25
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source
-
Boiling point (°C)
114
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
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)
78.0
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
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)
0.003
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-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)
-
-
-
Degradation
Property
Value
Source; quality score; and other information
Interpretation
General biodegradability
-
Soil degradation (days)
DT₅₀ (typical)
-
-
-
DT₅₀ (lab at 20 °C)
-
-
-
DT₅₀ (field)
-
-
-
DT₉₀ (lab at 20 °C)
-
-
-
DT₉₀ (field)
-
-
-
DT₅₀ modelling endpoint
-
-
-
Note
-
Soil mineralisation
Aerobic (at 20 °C)
-
-
-
Anaerobic (at 20 °C)
-
-
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.
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)
-
-
-
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)
-
-
-
Beneficial insects (Butterflies)
Contact
-
-
-
Notes
-
Oral
-
-
-
Notes
-
Aquatic ecotoxicology
Property
Value
Source; quality score; and other information
Interpretation
Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
6.35
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
Oncorhynchus mykiss
Moderate
Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)
-
-
-
Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
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
Mammals - Long Term (Chronic) Oral NOAEL (mg kg⁻¹ bw d⁻¹)
-
-
-
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
-
Mammals - Inhalation LC₅₀ (mg l⁻¹)
> 5.0
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
Rat 4 hr (whole body)
-
Other Mammal toxicity endpoints
-
-
-
ADI - Acceptable Daily Intake (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
-
ARfD - Acute Reference Dose (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
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 (%)
-
-
-
Dangerous Substances Directive 76/464
-
-
-
Exposure Routes
Public
-
Occupational
-
Mammalian dose elimination route and rate
-
-
-
Health issues
Specific human health issues (hazard-based)
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
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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Ecotoxicity
Human health
