Acrylonitrile (Ref: ENT 54)	Last updated: 16/12/2020
(Also known as: cyano ether; vinyl cyanide; propene nitrile; 2-propenenitrle)

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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 COPR regulatory status	Not approved
Date COPR inclusion expires	Not applicable
UK LERAP status	No UK approval for use

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

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
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
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		-

Fate indices

Property		Value	Source; quality score; and other information	Interpretation
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	-
Potential for loss via drain flow		Very mobile	Calculated	-

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)	-		-
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)		-	-	-
Birds - Acute LD₅₀ (mg kg⁻¹)		-	-	-
Birds - Short term dietary (LC₅₀/LD₅₀)		-	-	-
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)		-	-	-
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

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Record last updated:	16/12/2020
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