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Propetamphos (Ref: OMS 1502)
Last updated: 22/08/2024
(Also known as: safrotin; SAN 521391)
GENERAL INFORMATION
Description
An obsolete organophosphate insecticide and acaricide
Availability status
Current
Introduction & key dates
circa 1975, introduced
Examples of veterinary uses
Mainly used to control cockroaches, flies, ants, ticks, moths, fleas and mosquitoes in livestock situations
Examples of species treated
Sheep
Approval status
VMR 2013/2033 approval status (GB/UK)
Not approved
EU Regulatory approval status
Not approved
Chemical structure
Isomerism
Propetamophos is a chiral molecule. The technical material tends to consist of 4 isomer: 2 geometric isomers (cis & trans) and 2 optical isomers (S- and R-). The S-form is the dominate isomer and usually exceeds 90% of the techinal material.
Chemical formula
C₁₀H₂₀NO₄PS
Canonical SMILES
CCNP(=S)(OC)OC(=CC(=O)OC(C)C)C
Isomeric SMILES
CCNP(=S)(OC)O/C(=C/C(=O)OC(C)C)/C
International Chemical Identifier key (InChIKey)
BZNDWPRGXNILMS-VQHVLOKHSA-N
International Chemical Identifier (InChI)
InChI=1S/C10H20NO4PS/c1-6-11-16(17,13-5)15-9(4)7-10(12)14-8(2)3/h7-8H,6H2,1-5H3,(H,11,17)/b9-7+/f/h11H
2D structure diagram/image available?
Yes
General status
Veterinary substance type
Insecticide, Acaricide, Antiparasitic, Sheep dip
Substance groups
Organophosphate insecticide; Organophosphate acaricide; Phosphoramidothioate insecticide; Phosphoramidothioate acaricide
Minimum active substance purity
-
Known relevant impurities
-
Substance origin
Synthetic
Mode of action
Contact and stomach action with long residual activity; Acetylcholinesterase (AChE) inhibitor.
Molecular targets
[Cholinesterase, Inhibitor]
CAS RN
31218-83-4
EC number
250-517-2
CIPAC number
394
US EPA chemical code
113601
PubChem CID
5372405
CLP index number
015-136-00-6
Therapeutic Class
Antiparasitic products, insecticides & repellents: Ecoparasiticides, insecticides & repellents
ATCvet Code
QP53AF09
Controlled Drug?
No
Regulation 37/2010 MRL Classification
-
Molecular mass
281.31
PIN (Preferred Identification Name)
-
IUPAC name
(RS)-[(E)-O-2-isopropoxycarbonyl-1-methylvinyl O-methyl ethylphosphoramidothioate]
CAS name
1-methylethyl (2E)-3-[[(ethylamino)methoxyphosphinothioyl]oxy]-2-butenoate
Other status information
Marine, Surface and Groundwater Pollutant; PAN listed Highly Hazardous Chemical
Relevant Environmental Water Quality Standards
UK non-statutory standard for the protection of aquatic life: freshwater and saltwater annual average; 0.03 µg l⁻¹, max acceptable conc: 0.1 µg l⁻¹
Physical state
Oily yellow liquid
Formulations
Property
Product
Manufacturer
Authorisation Route
Legal Class (GB/UK)
Example products (past and present) 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)
110
G4 G = Extension Toxicology network database EXTOXNET. Available online but no longer updated. (click here )
4 = Verified data
at 24 °C		 Moderate
Solubility - In organic solvents at 20 °C (mg l⁻¹)
Miscible
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Ethanol		 -
Miscible
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Methanol		 -
Miscible
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Xylene		 -
Miscible
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Hexane		 -
Melting point (°C)
Not applicable
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 -
Boiling point (°C)
87
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 -
Degradation point (°C)
- - -
Flashpoint (°C)
- - -
Octanol-water partition coefficient at pH 7, 20 °C
P
6.61 X 1003 Calculated -
Log P
3.82
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 High
Fat solubility of residues
Solubility
- - -
Data type
- - -
Density (g ml⁻¹)
1.13
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 -
Dissociation constant pKa) at 25 °C
13.67
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 -
Strong base
Vapour pressure at 20 °C (mPa)
1.9
G4 G = Extension Toxicology network database EXTOXNET. Available online but no longer updated. (click here )
4 = Verified data
 Low volatility. If applied directly to plants or soil, drift is a concern & mitigation is advisable
Henry's law constant at 25 °C (Pa m³ mol⁻¹)
4.87 X 10-03
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
 Non-volatile
Volatilisation as max % of applied dose lost
From plant surface
- - -
From soil surface
- - -
Maximum UV-vis absorption L mol⁻¹ cm⁻¹
- - -
Surface tension (mN m⁻¹)
- - -
Refractive Index
1.495
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 -
Environmental release
-
Degradation
Property
Value
Source; quality score; and other information
Interpretation
Soil degradation (days) (aerobic)
DT₅₀ (typical)
20
S1 S = Expert judgement
1 = Estimated data with little or no verification
 Non-persistent
DT₅₀ (lab at 20 °C)
30
F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
3 = Unverified data of known source
 Moderately persistent
DT₅₀ (field)
- - -
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
Note
Best available data
Manure DT₅₀ (days)
- - -
Aqueous photolysis DT₅₀ (days) at pH 7
Value
Stable
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 Stable
Note
-
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7
Value
120
C4 C = AGRITOX dataset. Dataset is no longer available.
4 = Verified data
 Persistent
Note
Other data: DT₅₀ 11 days at pH 3, 1 year at pH 6, 41 days at pH 9, all at 25 °C (L3)
Water-sediment DT₅₀ (days)
- - -
Water phase only DT₅₀ (days)
- - -
Sediment phase only DT₅₀ (days)
- - -
Air degradation
As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below.
Decay in stored produce DT₅₀
-
Soil adsorption and mobility
Property
Value
Source; quality score; and other information
Interpretation
Linear
Kd (mL g⁻¹)
-
F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment )
3 = Unverified data of known source
 Moderately mobile
Koc (mL g⁻¹)
330
Notes and range
Best available data
Freundlich
Kf (mL g⁻¹)
- - -
Kfoc (mL g⁻¹)
-
1/n
-
Notes and range
-
pH sensitivity
-
Fate indices
Property
Value
Source; quality score; and other information
Interpretation
GUS leaching potential index
2.19 Calculated Transition state
Bio-concentration factor
BCF (l kg⁻¹)
352
Q2 Q = Miscellaneous data from online sources
2 = Unverified data of unknown source
Estimated		 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)
75
G4 G = Extension Toxicology network database EXTOXNET. Available online but no longer updated. (click here )
4 = Verified data
Rat		 High
Mammals - Short term dietary NOEL
(mg kg⁻¹)
-
L2 L = Pesticide manuals and hard copy reference books / other sources
2 = Unverified data of unknown source
Rat 2 yr		 -
(ppm diet)
6 -
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)
- - -
Birds - Acute LD₅₀ (mg kg⁻¹)
45
G4 G = Extension Toxicology network database EXTOXNET. Available online but no longer updated. (click here )
4 = Verified data
Anas platyrhynchos		 High
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)
- - -
Chronic
- - -
Notes
-
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 bee species (1)
Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)
- - -
Mode of exposure
-
Other bee species (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
Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
4.6
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Oncorhynchus mykiss		 Moderate
Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)
- - -
Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
- - -
Temperate Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
0.015
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Daphnia magna		 High
Temperate Freshwater Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)
0.0001
P3 P = Other non-EU, UK or US Governments and Regulators
3 = Unverified data of known source
Daphnia magna		 High
Tropical Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
- - -
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)
- - -
Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)
2.9
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Pseudokirchneriella subcapitata		 Moderate
Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)
- - -
Mesocosm study data
NOEAEC mg l⁻¹
- - -
NOEAEC mg l⁻¹
- - -
Marine bivalves
- - -
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)
75
G4 G = Extension Toxicology network database EXTOXNET. Available online but no longer updated. (click here )
4 = Verified data
Rat		 High
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
2260
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat		 -
Mammals - Inhalation LC₅₀ (mg l⁻¹)
0.69
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat		 -
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
-
Mammalian dose elimination route and rate
In mammals it is completely metabolised and excreted via urine and exhaled air
R3 R = Peer reviewed scientific publications
3 = Unverified data of known source
 -
Health issues
Specific human health issues
Carcinogen
Genotoxic
Endocrine disruptor
XNo, known not 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
;
E3 E = Unspecified genotoxicity type (miscellaneous data source)
3 = Negative
XNo, known not to cause a problem
Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant
XNo, known not to cause a problem
✓Yes, known to cause a problem
✓Yes, known to cause a problem
Respiratory tract irritant Skin irritant Skin sensitiser
No data found
XNo, known not to cause a problem
 No data found
Eye irritant Phototoxicant  
No data found No data found  
General human health issues
No further information available
Handling issues
Property
Value and interpretation
General
IMDG Transport Hazard Class 6.1
CLP classification 2013
Health: H301
Environment: H400, H410
WHO Classification
Ib (Highly hazardous)
UN Number
UN3018
Waste disposal & packaging
-
Shelf-life, storage, stability and reactivity
-
TRANSLATIONS
Language
Name
English
propetamphos
French
propetamphos
German
Propetamphos
Danish
propetamphos
Italian
propetamfos
Spanish
propetamfos
Greek
propetamphos
Polish
propetamfos
Swedish
-
Hungarian
-
Dutch
-
Norwegian
-
Record last updated: 22/08/2024
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