Top Environmental Fate Ecotoxicology Human Health Translations
Home
A to Z: All
A to Z: Insecticides
A to Z: Herbicides
A to Z: Fungicides
A to Z: Other product constituents
Search
Support information
Edit history
Purchasing and licensing
EPN (Ref: OMS 219)
Last updated: 18/01/2021
(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 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 
Great Britain
GB MRL Register 
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

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