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Pyraclofos (Ref: OMS 3040)
Last updated: 05/02/2024
(Also known as: TIA 230)
GENERAL INFORMATION
Description
An obsolete organophosphate insecticide used for external and internal parasite control
Availability status
-
Introduction & key dates
1989, registered Japan
Examples of veterinary uses
Substance used for eradicating parasites such as helminths, nematodes, ticks and others
Examples of species treated
Cattle; Horses; Sheep; Pigs; Poultry; Cats; Dogs
Approval status
VMR 2013/2033 approval status (GB/UK)
Not approved
EU Regulatory approval status
Not approved
Chemical structure
Isomerism
A molecule with one chiral centre resulting in a pair of enantiomers: S-(+)- and R-(−)-pyraclofos
Chemical formula
C₁₄H₁₈ClN₂O₃PS
Canonical SMILES
CCCSP(=O)(OCC)OC1=CN(N=C1)C2=CC=C(C=C2)Cl
Isomeric SMILES
No data
International Chemical Identifier key (InChIKey)
QHGVXILFMXYDRS-UHFFFAOYSA-N
International Chemical Identifier (InChI)
InChI=1S/C14H18ClN2O3PS/c1-3-9-22-21(18,19-4-2)20-14-10-16-17(11-14)13-7-5-12(15)6-8-13/h5-8,10-11H,3-4,9H2,1-2H3
2D structure diagram/image available?
Yes
General status
Veterinary substance type
Antiparasitic, Insecticide
Substance groups
Organophosphate insecticide; Orgnothiophosphate insecticide; Phenylpyrazole insecticide
Minimum active substance purity
-
Known relevant impurities
-
Substance origin
Synthetic
Mode of action
Respiratory, contact and stomach action. Acetylcholinesterase inhibitor.
Molecular targets
[Cholinesterase, Inhibitor]
CAS RN
89784-60-1
Alternative/old CAS RN
77458-01-6
EC number
618-301-6
CIPAC number
None allocated
US EPA chemical code
-
PubChem CID
93460
CLP index number
No data found
Therapeutic Class
-
ATCvet Code
None allocated
Controlled Drug?
No
Regulation 37/2010 MRL Classification
-
Molecular mass
360.8
PIN (Preferred Identification Name)
-
IUPAC name
(RS)-[O-1-(4-chlorophenyl)pyrazol-4-yl O-ethyl S-propyl phosphorothioate]
CAS name
O-[1-(4-chlorophenyl)-1H-pyrazol-4-yl] O-ethyl S-propyl phosphorothioate
Other status information
Evidence of use in third world countries; PAN listed Highly Hazardous Chemical
Relevant Environmental Water Quality Standards
-
Physical state
Pale yellow oil
Formulations
Property
Product
Manufacturer
Authorisation Route
Legal Class (GB/UK)
Example products (past and present) using this active
Coopers Colleague Broad Spectrum Sheep & Lamb Drench Schering-Plough Animal Health Not licensed Not licensed
Formulation and application details
-
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
33
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 Low
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
Acetone		 -
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		 -
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)
454
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
5.89 X 1003 Calculated -
Log P
3.77
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)
1.271
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)
1.60 X 10-03
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)
1.75 X 10-05
L3 L = Pesticide manuals and hard copy reference books / other sources
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)
39
K4 K = Research datasets (e.g. Pandora, Demetra; these datasets no longer available). Norman Ecotoxicology database. (click here )
4 = Verified data
 Moderately persistent
DT₅₀ (lab at 20 °C)
- - -
DT₅₀ (field)
50
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 Moderately persistent
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
Note
Best available data
Manure DT₅₀ (days)
- - -
Aqueous photolysis DT₅₀ (days) at pH 7
Value
- - -
Note
-
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7
Value
29
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 Non-persistent
Note
-
Water-sediment DT₅₀ (days)
- - -
Water 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)
-
Q2 Q = Miscellaneous data from online sources
2 = Unverified data of unknown source
 Slightly mobile
Koc (mL g⁻¹)
2095
Notes and range
Estimated
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
1.15 Calculated Low leachability
Bio-concentration factor
BCF (l kg⁻¹)
- - -
CT₅₀ (days)
- -
Known soil and groundwater metabolites

None

Other known metabolites
Metabolite name and reference
Aliases
Formation medium / Rate
Estimated maximum occurrence fraction
1-(4-chlorophenyl)pyrazol-4-yl-6-O-malonyl-beta-D-glcopyranoside - Plant 0.51
1-(4-chlorophenyl)pyrazo-4-yl sulfate - Rat (Urine) 0.7
desethylpyraclofos - Rat (Urine, Faecal) -
1-(4-chlorophenyl)pyrazol-4-yl-beta-D-glcopyranoside - Plant -
des-S-propylpyraclofos - Rat (Urine, Faecal) -
O-ethyl-S-propyl-phosphorothioate - Rat (Urine) -
monoethylphosphate - Rat (Urine) -
ECOTOXICOLOGY
Terrestrial ecotoxicology
Property
Value
Source; quality score; and other information
Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
237
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
Rat		 Moderate
Mammals - Short term dietary NOEL
(mg kg⁻¹)
0.1
L2 L = Pesticide manuals and hard copy reference books / other sources
2 = Unverified data of unknown source
Rat 2 yr		 High
(ppm diet)
- -
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)
- - -
Birds - Acute LD₅₀ (mg kg⁻¹)
164
L3 L = Pesticide manuals and hard copy reference books / other sources
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)
- - -
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)
0.953
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Apis mellifera		 High
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
- - -
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)
0.028
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Cyprinidae spp.		 High
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)
- - -
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)
- - -
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
- - -
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)
237
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
Rat		 Moderate
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
2000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat		 -
Mammals - Inhalation LC₅₀ (mg l⁻¹)
1.46
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
Rapidly absorbed, metabolised and excreted in the urine
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
;
E0 E = Unspecified genotoxicity type (miscellaneous data source)
0 = No data
 No data found
Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant
?Possibly, status not identified
✓Yes, known to cause a problem
?Possibly, status not identified
Respiratory tract irritant Skin irritant Skin sensitiser
XNo, known not to cause a problem
XNo, known not to cause a problem
 No data found
Eye irritant Phototoxicant  
XNo, known not to cause a problem
 No data found  
General human health issues
Harmful if swallowed
Handling issues
Property
Value and interpretation
General
IMDG Transport Hazard Class 6.1
CLP classification 2013
Health: H301
WHO Classification
II (Moderately hazardous)
UN Number
UN2811
Waste disposal & packaging
Packaging Group III (minor danger)
Shelf-life, storage, stability and reactivity
-
TRANSLATIONS
Language
Name
English
pyraclofos
French
pyraclofos
German
Pyraclofos
Danish
pyraclofos
Italian
piraclofos
Spanish
piraclofos
Greek
-
Polish
pyraklofos
Swedish
-
Hungarian
-
Dutch
-
Norwegian
-
Record last updated: 05/02/2024
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