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Acrylonitrile (Ref: ENT 54)
Last updated: 09/12/2019
(Also known as: cyano ether; vinyl cyanide; propene nitrile; 2-propenenitrle)

SUMMARY
Acrylonitrile is a fumigant insecticide that is not approved for use within the EU and is now considered obsolete. It is highly soluble in water and miscible with most organic solvents. It has a high potential for leaching to groundwater. It is not expected to be persistant in soil systems. Acrylonitrile has a high mammalian toxicity and is carcinogenic It is also a mutagen which may also cause adverse reproduction &/or development effects. Little is known about its ecotoxicology but it is moderately toxic to fish and aquatic invertebrates.
GENERAL INFORMATION
Description
An obsolete pesticide that was used as a fumigant for insect control. It was also used for spot treatments in flour mills and bakeries.
Example pests controlled
Mites; Japanese beetle; Cigarette beetle; Tobacco moth; Flour beetle; Grain beetle
Example applications
Stored grain; Dried fruit and nuts; Harvested tobacco; Food processing sites; Flour mills
Efficacy & activity
-
Availability status
Obsolete
Introduction & key dates
-
UK regulatory status
UK approval status
Not approved
EC Regulation 1107/2009 (repealing 91/414)
EC Directive 91/414 Status
Not approved
Dossier rapporteur/co-rapporteur
Not applicable
Date inclusion expires
Not applicable
EU Candidate for substitution (CfS)
Not applicable
Listed in EU database
No
Approved for use (✓) or known to be used (#) in the following EU-27 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
                 
Also used in
Also used in
-
Chemical structure
Isomerism
-
Chemical formula
C₃H₃N
Canonical SMILES
C=CC#N
Isomeric SMILES
No data
International Chemical Identifier key (InChIKey)
NLHHRLWOUZZQLW-UHFFFAOYSA-N
International Chemical Identifier (InChI)
InChI=1S/C3H3N/c1-2-3-4/h2H,1H2
2D structure diagram/image available?
Yes
Cambridge Crystallographic Data Centre diagrams
Common Name Relationship Link
acrylonitrile -
General status
Pesticide type
Insecticide, Bactericide
Substance group
Unclassified
Minimum active substance purity
-
Known relevant impurities
-
Substance origin
Synthetic
Mode of action
Respiratory action.
CAS RN
107-13-1
EC number
203-466-5
CIPAC number
-
US EPA chemical code
000601
PubChem CID
7855
CLP index number
608-003-00-4
Molecular mass
53.06
PIN (Preferred Identification Name)
prop-2-enenitrile
IUPAC name
acrylonitrile
CAS name
acrylonitrile
Other status information
Not applicable
Relevant Environmental Water Quality Standards
-
Herbicide Resistance Classification (HRAC)
Not applicable
Herbicide Resistance Classification (WSSA)
Not applicable
Insecticide Resistance Classification (IRAC)
Not known
Fungicide Resistance Classification (FRAC)
Not applicable
Examples of recorded resistance
-
Physical state
Colourless to pale yellow liquid with a garlic type odour
Formulations
Property
Value
Example manufacturers & suppliers of products using this active now or historically
  • VCN
  • Ventox
  • Acritet
  • Acrylon
Example products using this active
  • American Cyanamid Co., Degesh
  • Stauffer
UK LERAP status
No UK approval for use as a pesticide under EC Regulation 1107/2009
Formulation and application details
Fumigant
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
76000
R4 R = Peer reviewed scientific publications
4 = Verified data
High
Solubility - In organic solvents at 20 °C (mg l⁻¹)
100000
R4 R = Peer reviewed scientific publications
4 = Verified data
Methanol
-
100000
R4 R = Peer reviewed scientific publications
4 = Verified data
Ethyl acetate
-
100000
R4 R = Peer reviewed scientific publications
4 = Verified data
Acetone
-
100000
R4 R = Peer reviewed scientific publications
4 = Verified data
Heptane
-
Melting point (°C)
-84
R4 R = Peer reviewed scientific publications
4 = Verified data
-
Boiling point (°C)
77
R4 R = Peer reviewed scientific publications
4 = Verified data
-
Degradation point (°C)
- - -
Flashpoint (°C)
- - -
Octanol-water partition coefficient at pH 7, 20 °C
P
1.20 X 10-01 Calculated -
Log P
-0.92
R4 R = Peer reviewed scientific publications
4 = Verified data
Low
Bulk density (g ml⁻¹)
0.81
R4 R = Peer reviewed scientific publications
4 = Verified data
-
Dissociation constant pKa) at 25 °C
- - -
-
Vapour pressure at 20 °C (mPa)
1.37 X 1007
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Highly volatile
Henry's law constant at 25 °C (Pa m³ mol⁻¹)
0.063
R4 R = Peer reviewed scientific publications
4 = Verified data
Non-volatile
GUS leaching potential index
3.58 Calculated High leachability
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate
Value
2.82 X 10-01 Calculated -
Note
-
Potential for particle bound transport index
Low Calculated -
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)
15
F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (US EPA Databases Related to Pesticide Risk Assessment )
3 = Unverified data of known source
Non-persistent
DT₅₀ (lab at 20 °C)
- - -
DT₅₀ (field)
- - -
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
DT₅₀ modelling endpoint
- - -
Note
Literature states degradation in activated sewage sludge is complete in 20 days
Dissipation rate RL₅₀ on plant matrix
Value
- - -
Note
-
Dissipation rate RL₅₀ 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)
- - -
Soil adsorption and mobility
Property
Value
Source; quality score; and other information
Interpretation
Linear
Kd
-
R4 R = Peer reviewed scientific publications
4 = Verified data
Very mobile
Koc
9.0
Notes and range
-
Freundlich
Kf
- - -
Kfoc
-
1/n
-
Notes and range
-
pH sensitivity
-
Other known metabolites
Metabolite name and reference
Aliases
Formation medium / Rate
Estimated maximum occurrence fraction
Metabolising enzymes
2-cyanolethylene oxide - - - -
glycidonitrile - Rat - -
pyruvonitrile - Rat - -
cyanoacetaldehyde - Rat - -
cyanoacetic acid - Rat - -
2-cyanoethanol - Rat - -
glycoladehyde - Rat - -
ECOTOXICOLOGY
Property
Value
Source; quality score; and other information
Interpretation
Bio-concentration factor
BCF (l kg⁻¹)
48
R4 R = Peer reviewed scientific publications
4 = Verified data
Low potential
CT₅₀ (days)
Not available -
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
78.0
R4 R = Peer reviewed scientific publications
4 = Verified data
Rat
High
Mammals - Short term dietary NOEL
(mg kg⁻¹)
- - -
(ppm diet)
- -
Birds - Acute LD₅₀ (mg kg⁻¹)
- - -
Birds - Short term dietary (LC₅₀/LD₅₀)
- - -
Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
10.1
R4 R = Peer reviewed scientific publications
4 = Verified data
Pimephales promelas
Moderate
Fish - Chronic 21 day NOEC (mg l⁻¹)
- - -
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
7.6
R4 R = Peer reviewed scientific publications
4 = Verified data
Daphnia magna
Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)
0.5
P4 P = Other governments and regulators
4 = Verified data
Daphnia magna
Moderate
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)
- - -
Non-target plants
- - -
- - -
Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)
- - -
Algae - Chronic 96 hour NOEC, growth (mg l⁻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)
- - -
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 pollinators (1)
Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)
- - -
Mode of exposure
-
Other pollinators (2)
Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)
- - -
Mode of exposure
-
Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)
- - -
Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)
- - -
Other soil macro-organisms
Acute LC₅₀ (mg kg⁻¹)
- - -
Chronic NOEC (mg kg⁻¹)
- - -
Other arthropod (1)
LR₅₀ g ha⁻¹
- - -
% Effect
- - -
Other arthropod (2)
LR₅₀ g ha⁻¹
- - -
% Effect
- - -
Soil micro-organisms
- - -
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)
High (class III) - -
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
78.0
R4 R = Peer reviewed scientific publications
4 = Verified data
Rat
High
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
- - -
Mammals - Inhalation LC₅₀ (mg l⁻¹)
- - -
Other Mammal toxicity endpoints
Intravenous LD₅₀ = 69 mg kg⁻¹
R4 R = Peer reviewed scientific publications
4 = Verified data
Rabbit
-
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
Acrylonitrile will permeate through the skin
European MRLs
EU MRL pesticide database 
Drinking Water Standards
- - -
Drinking Water MAC (μg l⁻¹)
- - -
Health issues
Specific human health issues
Carcinogen
Genotoxic
Endocrine disruptor
?Possibly, status not identified
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
;
E1 E = Unspecified genotoxicity type (miscellaneous data source)
1 = Positive
No data found
Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant
Yes, known to cause a problem
No data found No data found
Respiratory tract irritant Skin irritant Skin sensitiser
Yes, known to cause a problem
Yes, known to cause a problem
?Possibly, status not identified
Eye irritant Phototoxicant  
Yes, known to cause a problem
No data found  
General human health issues
May cause light jaundice, leucoytosis, headaches and gastro-intestinal problems
Liver and kidney toxicant
IARC group 2B carcinogen
Handling issues
Property
Value and interpretation
General
May emit toxic fumes of cyanide on heating
May be explosive under some conditions
Flammable
CLP classification 2013
Health: H350, H331, H311, H301, H335, H315
Environment: H411
EC Risk Classification
Carcinogen category 2: R45
T - Toxic: R23/24/25
Xn - Harmful: R43
Xi - Irritant: R37/38
N - Dangerous for the environment: R51/53
EC Safety Classification
-
WHO Classification
FM (Fumigant, not classified)
UN Number
-
Waste disposal & packaging
-
TRANSLATIONS
Language
Name
English
acrylonitrile
French
nitrile acrylique
German
Acrylnitril
Danish
-
Italian
Nitrile acrilico
Spanish
-
Greek
-
Polish
-
Swedish
-
Hungarian
-
Dutch
acrylnitril

Record last updated: 09/12/2019
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