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Propetamphos (Ref: OMS 1502)
Last updated: 03/03/2021
(Also known as: safrotin; SAN 521391)
GENERAL INFORMATION
Description
A insecticide and acaricide for use in public health and livestock situations
Example pests controlled
Cockroaches; Flies; Ants; Moths; Fleas; Ticks; Mosquitoes; Termites
Example applications
Public health applications; Landscape management; Non-cropped areas including rights-of-way, footpaths
Efficacy & activity
-
Availability status
Current
Introduction & key dates
circa 1975
UK regulatory status
UK COPR regulatory status
Not approved
Date COPR inclusion expires
Expired
UK LERAP status
Not applicable
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
Expired
EU Candidate for substitution (CfS)
-
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
Australia
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
Pesticide type
Insecticide, Acaricide, Veterinary substance
Substance group
Organophosphate
Minimum active substance purity
-
Known relevant impurities
-
Substance origin
Synthetic
Mode of action
Contact and stomach action with long residual activity; Acetylcholinesterase (AChE) inhibitor.
CAS RN
31218-83-4
EC number
250-517-2
CIPAC number
394
US EPA chemical code
113601
PubChem CID
5372405
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
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
Blattella germanica, Bulex pipiens molestus, Bulex pipiens pipiens, Musca domestica, Rhipicephalus bursa
Physical state
Oily yellow liquid
Formulations
Property
Value
Example manufacturers & suppliers of products using this active now or historically
  • Safrotin
Example products using this active
  • Sandoz
Formulation and application details
Usually supplied as a liquid concentrate for application as spot, surface, and crack and crevice treatments via low pressure spray or injected into the soil for termites.
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 (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
Bulk 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 (click here )
4 = Verified data
 Low volatility
Henry's law constant at 25 °C (Pa m³ mol⁻¹)
4.87 X 10-03
V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM )
3 = Unverified data of known source
 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)
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 (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)
- - -
DT₅₀ modelling endpoint
- - -
Note
Best available data
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
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 (click here )
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)
- - -
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
 Moderately mobile
Koc
330
Notes and range
Best available data
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
2.19 Calculated Transition state
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate
Value
9.27 X 10-02 Calculated -
Note
-
Potential for particle bound transport index
Low Calculated -
Potential for loss via drain flow
Moderately mobile Calculated -
ECOTOXICOLOGY
Property
Value
Source; quality score; and other information
Interpretation
Bio-concentration factor
BCF (l kg⁻¹)
352
Q2 Q = Miscellaneous internet resources
2 = Unverified data of unknown source
Estimated		 Threshold for concern
CT₅₀ (days)
Not available -
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
75
G4 G = Extension Toxicology network database EXTOXNET (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 year		 -
(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 (click here )
4 = Verified data
Anas platyrhynchos		 High
Birds - Short term dietary (LC₅₀/LD₅₀)
- - -
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)
- - -
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
Fish - Chronic 21 day NOEC (mg l⁻¹)
- - -
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
Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)
0.0001
P3 P = Other governments and regulators
3 = Unverified data of known source
Daphnia magna		 High
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)
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)
- - -
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)
75
G4 G = Extension Toxicology network database EXTOXNET (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
-
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
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
No information available
CLP classification 2013
Health: H301
Environment: H400, H410
EC Risk Classification
T - Toxic: R25
N - Dangerous for the environment: R50, R53
EC Safety Classification
S1/2, S37, S45, S60, S61
WHO Classification
Ib (Highly hazardous / Highly hazardous)
UN Number
3018
Waste disposal & packaging
-
TRANSLATIONS
Language
Name
English
propetamphos
French
propetamphos
German
Propetamphos
Danish
propetamphos
Italian
propetamfos
Spanish
propetamfos
Greek
propetamphos
Polish
propetamfos
Swedish
-
Hungarian
-
Dutch
-
Record last updated: 03/03/2021
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