EPN (Ref: OMS 219)

EPN (Ref: OMS 219)	Last updated: 16/01/2023
(Also known as: ENT 17298; HSDB 4049; tsumaphos)

SUMMARY

Data 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.

Environmental fate	Ecotoxicity	Human health
Environmental fate Moderate alert: Potential for particle bound transport: Medium	Ecotoxicity High alert: Fish chronic ecotoxicity: High; Daphnia acute ecotoxicity: High; Daphnia chronic ecotoxicity: High; Bees acute unknown ecotoxicity: High	Human health High alert: Mammals acute toxicity: High; Carcinogen; Acetyl cholinesterase inhibitor; Neurotoxicant

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

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

Additional information

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 groups

Organophosphate insecticide; Organophosphate acaricide; Phenyl phenylphosphonothioate insecticide; Phenyl phenylphosphonothioate acaricide

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

CLP index number

015-036-00-2

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)

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

Low

Solubility - In organic solvents at 20 °C (mg l⁻¹)

Melting point (°C)

34.5

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

Octanol-water partition coefficient at pH 7, 20 °C

1.05 X 10⁰⁵

Calculated

Log P

5.02

High

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.27

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

0.041

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)

Non-persistent

DT₅₀ (lab at 20 °C)

DT₅₀ (field)

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

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

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

K_d

Non-mobile

K_oc

4000

Notes and range

Freundlich

K_f

K_foc

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

Bio-concentration factor

BCF (l kg⁻¹)

2346

Threshold for concern

CT₅₀ (days)

Not available

Known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

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

Colinus virginianus

Moderate

Birds - Short term dietary (LC₅₀/LD₅₀)

Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)

Soil micro-organisms

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

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

Apis mellifera

High

Chronic

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

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 0.110

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

0.020

Pimephales promelas survival

Moderate

Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

0.00006

Daphnia magna

High

Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)

0.000037

Daphnia magna

High

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

0.003

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)

Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)

Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)

Mesocosm study data

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)

Rat

High

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

538

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

0.106

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

Great Britain

GB MRL Register

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Mammalian dose elimination route and rate

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

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

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

Record last updated:	16/01/2023
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