EPN (Ref: OMS 219)	Last updated: 18/01/2021
(Also known as: ENT 17298; HSDB 4049; tsumaphos)

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GENERAL INFORMATION

Description	Used to control Lepidoptera larva, especially bollworms in a range of crops including cotton
Example pests controlled	Bollworms; Rice stem borer; Oriental fruit moth; Armyworms; Leaf miners; Mexican bean beetles; Leafrollers; Tobacco budworm; Boll weevils
Example applications	Cotton; Rice; Fruit; Vegetables; Tobacco
Efficacy & activity	-
Availability status	Unknown
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	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

Also used in

Also used in	-

Chemical structure

Isomerism	EPN is a chiral molecule having a have a (+)- and a (−)-isomer. Commercial products are isomeric mixtures with the (+)-form showing the greatest insecticidal activity and also the least neurotoxicity.
Chemical formula	C₁₄H₁₄NO₄PS
Canonical SMILES	CCOP(=S)(C1=CC=CC=C1)OC2=CC=C(C=C2)[N+](=O)[O-]
Isomeric SMILES	No data
International Chemical Identifier key (InChIKey)	AIGRXSNSLVJMEA-UHFFFAOYSA-N
International Chemical Identifier (InChI)	InChI=1S/C10H13NO2/c1-7-4-8(2)6-9(5-7)13-10(12)11-3/h4-6H,1-3H3,(H,11,12)
2D structure diagram/image available?	Yes

General status

Pesticide type	Insecticide, Acaricide
Substance group	Organophosphate
Minimum active substance purity	-
Known relevant impurities	-
Substance origin	Synthetic
Mode of action	Non-systemic with contact and stomach action, works by cholinesterase inhibition
CAS RN	2104-64-5
EC number	218-276-8
CIPAC number	302
US EPA chemical code	041801
PubChem CID	16421
Molecular mass	323.30
PIN (Preferred Identification Name)	(E)-[O-ethyl O-(4-nitrophenyl) phenylphosphonothioate]
IUPAC name	(RS)-(O-ethyl O-4-nitrophenyl phenylphosphonothioate)
CAS name	O-ethyl O-(4-nitrophenyl) phenylphosphonothioate
Other status information	Severe Marine Pollutant
Relevant Environmental Water Quality Standards	-
Herbicide Resistance Classification (HRAC)	Not applicable
Herbicide Resistance Classification (WSSA)	Not applicable
Insecticide Resistance Classification (IRAC)	1B
Fungicide Resistance Classification (FRAC)	Not applicable
Examples of recorded resistance	Chilo suppressalis, Plutella xylostella, Psylla pyricola, Tetranychus bimaculatus
Physical state	Yellow crystals

Formulations

Property	Value
Example manufacturers & suppliers of products using this active now or historically	-
Example products using this active	-
Formulation and application details	-

ENVIRONMENTAL FATE

Property		Value	Source; quality score; and other information	Interpretation
Solubility - In water at 20 °C (mg l⁻¹)		0.5	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	Low
Solubility - In organic solvents at 20 °C (mg l⁻¹)		-	-	-
Melting point (°C)		34.5	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	-
Boiling point (°C)		-	-	-
Degradation point (°C)		-	-	-
Flashpoint (°C)		-	-	-
Octanol-water partition coefficient at pH 7, 20 °C	P	1.05 X 1005	Calculated	-
	Log P	5.02	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	High
Bulk density (g ml⁻¹)		1.27	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	-
Dissociation constant pKa) at 25 °C		-	-	-
		-
Vapour pressure at 20 °C (mPa)		0.041	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	Low volatility
Henry's law constant at 25 °C (Pa m³ mol⁻¹)		-	-	-
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)	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
	DT₉₀ (lab at 20 °C)	-	-	-
	DT₉₀ (field)	-	-	-
	DT₅₀ modelling endpoint	-	-	-
	Note	USDA data; Other data sources quote DT₅₀ <15 days in paddy fields
Dissipation rate RL₅₀ on plant matrix	Value	4.0	R4 R = Peer reviewed scientific publications 4 = Verified data	-
	Note	Published literature RL₅₀ range 1.0-7.0 days, cotton leaves, n=2
Dissipation rate RL₅₀ on and in plant matrix	Value	5.6	R4 R = Peer reviewed scientific publications 4 = Verified data	-
	Note	Published literature RL₅₀ range 3.0-10.0 days, fruit & leaves of 2 orchard crops, n=4
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	-	US3 US = US Dept of Agriculture National Resources Conservation Service - various datasheets, databases and online sources 3 = Unverified data of known source	Non-mobile
	Koc	4000
	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		0.47	Calculated	Low leachability
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate	Value	8.95 X 10-03	Calculated	-
	Note	-
Potential for particle bound transport index		Medium	Calculated	-
Potential for loss via drain flow		Non-mobile	Calculated	-

ECOTOXICOLOGY

Property		Value	Source; quality score; and other information	Interpretation
Bio-concentration factor	BCF (l kg⁻¹)	2346	R3 R = Peer reviewed scientific publications 3 = Unverified data of known source	Threshold for concern
	CT₅₀ (days)	Not available		-
Mammals - Acute oral LD₅₀ (mg kg⁻¹)		14	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 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)		> 289	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 Colinus virginianus	Moderate
Birds - Short term dietary (LC₅₀/LD₅₀)		-	-	-
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)		-	-	-
Fish - Acute 96 hour LC₅₀ (mg l⁻¹)		> 0.110	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 Oncorhynchus mykiss	Moderate
Fish - Chronic 21 day NOEC (mg l⁻¹)		0.020	P3 P = Other governments and regulators 3 = Unverified data of known source Pimephales promelas survival	Moderate
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)		0.00006	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 Daphnia magna	High
Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)		0.000037	P3 P = Other governments and regulators 3 = Unverified data of known source Daphnia magna	High
Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)		0.003	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 Americamysis bahia	High
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)	0.237	Q3 Q = Miscellaneous internet resources 3 = Unverified data of known source	High
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)		14	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 Rat	High
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)		538	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Rat	-
Mammals - Inhalation LC₅₀ (mg l⁻¹)		0.106	V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM ) 3 = Unverified data of known source Rat 1 hr	-
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		List I; List II	-	-
Exposure Routes	Public	-
	Occupational	May be absorbed through the skin
MRLs	European	EU MRL pesticide database
	Notes	-
Drinking Water Standards		-	-	-
Drinking Water MAC (μg l⁻¹)		-	-	-

Health issues

Specific human health issues		Carcinogen Genotoxic Endocrine disruptor ✓Yes, known 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 ; E0 E = Unspecified genotoxicity type (miscellaneous data source) 0 = No data No data found Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant No data found ✓Yes, known to cause a problem ✓Yes, known to cause a problem Respiratory tract irritant Skin irritant Skin sensitiser No data found No data found No data found Eye irritant Phototoxicant   No data found No data found
General human health issues		Inhalation and ingestion may cause a variety of symptons including convulsions, dizziness, sweating, breathing difficulties, nausea and unconsciousness

Handling issues

Property	Value and interpretation
General	IMDG Transport Code is 6.1
CLP classification 2013	Health: H300, H310 Environment: H400, H410
EC Risk Classification	T+ - Highly toxic: R27/28 N - Dangerous for the environment: R50, R53
EC Safety Classification	S1/2, S22, S36/37, S45, S60, S61
WHO Classification	Ia (Extremely hazardous)
UN Number	2783
Waste disposal & packaging	-

TRANSLATIONS

Language	Name
English	EPN
French	EPN
German	EPN
Danish	EPN
Italian	EPN
Spanish	EPN
Greek	EPN
Polish	EPN
Swedish	EPN
Hungarian	EPN
Dutch	EPN

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Record last updated:	18/01/2021
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