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Temephos (Ref: OMS 786)
Last updated: 22/08/2024
(Also known as: ENT 27165; abaphos; abathion; biothion; difenphos)
GENERAL INFORMATION
Description
A nonsystemic organophosphorus insecticide used to control ecoparasites
Availability status
Current
Introduction & key dates
1965, introduced
Examples of veterinary uses
Used to control mosquito, midge, and black fly larvae
Examples of species treated
Sheep; Cats; Dogs
Approval status
VMR 2013/2033 approval status (GB/UK)
Not appproved
EU Regulatory approval status
Not approved
Chemical structure
Isomerism
None
Chemical formula
C₁₆H₂₀O₆P₂S₃
Canonical SMILES
COP(=S)(OC)OC1=CC=C(C=C1)SC2=CC=C(C=C2)OP(=S)(OC)OC
Isomeric SMILES
-
International Chemical Identifier key (InChIKey)
WWJZWCUNLNYYAU-UHFFFAOYSA-N
International Chemical Identifier (InChI)
InChI=1S/C16H20O6P2S3/c1-17-23(25,18-2)21-13-5-9-15(10-6-13)27-16-11-7-14(8-12-16)22-24(26,19-3)20-4/h5-12H,1-4H3
2D structure diagram/image available?
Yes
General status
Veterinary substance type
Insecticide
Substance groups
Organophosphate insecticide; Organothiophosphate insecticide
Minimum active substance purity
-
Known relevant impurities
-
Substance origin
Synthetic
Mode of action
Non-systemic. Acetylcholinesterase (AChE) inhibitor.
Molecular targets
[Cholinesterase, Inhibitor]
CAS RN
3383-96-8
EC number
222-191-1
CIPAC number
340
US EPA chemical code
059001
PubChem CID
5392
CLP index number
No data found
Therapeutic Class
-
ATCvet Code
None allocated
Controlled Drug?
No
Regulation 37/2010 MRL Classification
-
Molecular mass
466.47
PIN (Preferred Identification Name)
O,O,O',O'-tetramethyl O,O'-(sulfanediyldi-4,1-phenylene) bis(phosphorothioate)
IUPAC name
O,O,O',O'-tetramethyl O,O'-thiodi-p-phenylene bis(phosphorothioate)
CAS name
O,O'-(thiodi-4,1-phenylene) bis(O,O-dimethyl phosphorothioate)
Other status information
Marine Pollutant; Evidence of use in third world countries; PAN listed Highly Hazardous Chemical
Relevant Environmental Water Quality Standards
-
Physical state
Colourless crystals
Formulations
Property
Product
Manufacturer
Authorisation Route
Legal Class (GB/UK)
Example products (past and present) using this active
Coopers Assassin Sheep Dip Intervet Australia Pty Limited No GB authorisation for use with animals Not applicable
Stopmos 1G Ivorychem PTE, Singapore No GB authorisation for use with animals Not applicable
Formulation and application details
-
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
0.001
M4 M = GLEAMS Model database (Groundwater Loading Effects of Agricultural Management Systems). Dataset no longer available.
4 = Verified data
 Low
Solubility - In organic solvents at 20 °C (mg l⁻¹)
9600
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Hexane		 -
Melting point (°C)
30.3
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
8.91 X 1004 Calculated -
Log P
4.95
G4 G = Extension Toxicology network database EXTOXNET. Available online but no longer updated. (click here )
4 = Verified data
 High
Fat solubility of residues
Solubility
- - -
Data type
- - -
Density (g ml⁻¹)
1.32
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)
9.50 X 10-03
K4 K = Research datasets (e.g. Pandora, Demetra; these datasets no longer available). Norman Ecotoxicology database. (click here )
4 = Verified data
 Low volatility
Henry's law constant at 25 °C (Pa m³ mol⁻¹)
1.99 X 10-04
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
- - -
Environmental release
-
Degradation
Property
Value
Source; quality score; and other information
Interpretation
Soil degradation (days) (aerobic)
DT₅₀ (typical)
2
K4 K = Research datasets (e.g. Pandora, Demetra; these datasets no longer available). Norman Ecotoxicology database. (click here )
4 = Verified data
 Non-persistent
DT₅₀ (lab at 20 °C)
30
DW4 DW = Don Wauchope personal database for Pka data: Wauchope, R. D. and Edwards, J. Dissociation constants for pesticide active ingredients: a database and comparison with predicted values. Dataset is no longer available.
4 = Verified data
 Moderately persistent
DT₅₀ (field)
- - -
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
Note
General literature DT₅₀ approx 2 days (R3)
Manure DT₅₀ (days)
- - -
Aqueous photolysis DT₅₀ (days) at pH 7
Value
2
K4 K = Research datasets (e.g. Pandora, Demetra; these datasets no longer available). Norman Ecotoxicology database. (click here )
4 = Verified data
 Moderately fast
Note
-
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7
Value
10
K4 K = Research datasets (e.g. Pandora, Demetra; these datasets no longer available). Norman Ecotoxicology database. (click here )
4 = Verified data
 Non-persistent
Note
-
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)
-
G4 G = Extension Toxicology network database EXTOXNET. Available online but no longer updated. (click here )
4 = Verified data
 Non-mobile
Koc (mL g⁻¹)
100000
Notes and range
-
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
-1.48 Calculated Low leachability
Bio-concentration factor
BCF (l kg⁻¹)
2300
F4 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 )
4 = Verified data
Whole fish		 Threshold for concern
CT₅₀ (days)
Not available -
Known soil and groundwater metabolites

None

Other known metabolites
Metabolite name and reference
Aliases
Formation medium / Rate
Estimated maximum occurrence fraction
4,4-sulfonyldiphenol - Rat (Faecal) -
temephos sulfoxide - Plant; Rat (Faecal) -
ECOTOXICOLOGY
Terrestrial ecotoxicology
Property
Value
Source; quality score; and other information
Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
4204
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat		 Low
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)
300 -
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)
- - -
Birds - Acute LD₅₀ (mg kg⁻¹)
> 1200
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Anas platyrhynchos		 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)
> 1000
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
Eisenia foetida		 Low
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)
> 1.55
G4 G = Extension Toxicology network database EXTOXNET. Available online but no longer updated. (click here )
4 = Verified data
Apis mellifera		 Moderate
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)
> 3.49
J4 J = Pesticide Action Network database (click here )
4 = Verified data
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)
0.00001
J4 J = Pesticide Action Network database (click here )
4 = Verified data
Daphnia magna		 High
Temperate Freshwater Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)
- - -
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)
0.0040
R4 R = Peer reviewed scientific publications
4 = Verified data
Chironomus salinarius 24 hr		 High
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)
1.4
W2 W = French database provided by ARVALIS-Institut du Végétal. Dataset no longer available.
2 = Unverified data of unknown source
Unknown species		 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)
4204
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat		 Low
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
2181
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rabbit		 -
Mammals - Inhalation LC₅₀ (mg l⁻¹)
4.79
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat		 -
Other Mammal toxicity endpoints
Intraperitoneal LD₅₀ = 912 mg kg⁻¹
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
Rat		 -
Subcutaneous LD₅₀ = 912 mg kg⁻¹
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
Rat		 -
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
Dietary risks from food and drinking water are not of concern due to pattern of use
Occupational
-
Mammalian dose elimination route and rate
Excreted mainly unchanged in the faeces
Q3 Q = Miscellaneous data from online sources
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
;
E2 E = Unspecified genotoxicity type (miscellaneous data source)
2 = Mixed/ambiguous results
 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
XNo, known not to cause a problem
 No data found
Eye irritant Phototoxicant  
?Possibly, status not identified
 No data found  
General human health issues
No further information available
Handling issues
Property
Value and interpretation
General
Prevent generation of dust and mists
IMDG Transport Hazard Class 6.1
CLP classification 2013
Health: H302, H311, H332, H373
Environment: H400, H410
WHO Classification
III (Slightly hazardous)
UN Number
UN2811
Waste disposal & packaging
Packaging Group III (minor danger)
Shelf-life, storage, stability and reactivity
Stable and non-reactive under normal conditions of use, storage and transport
TRANSLATIONS
Language
Name
English
temephos
French
temephos
German
Temephos
Danish
temephos
Italian
temefos
Spanish
temefos
Greek
-
Polish
temefos
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