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Phoxim (Ref: OMS 1170)
Last updated: 22/08/2024
(Also known as: phoxime; BAY 5621)
GENERAL INFORMATION
Description
An obsolete organophosphate insecticide used to control external animal parasites
Availability status
-
Introduction & key dates
1970, introduced
Examples of veterinary uses
Used topically to control mites, lice and other ectoparasites
Examples of species treated
Cattle; Sheep; Goats; Pigs
Approval status
VMR 2013/2033 approval status (GB/UK)
Not approved
EU Regulatory approval status
Not approved
Chemical structure
Isomerism
Isomeric
Chemical formula
C₁₂H₁₅N₂O₃PS
Canonical SMILES
CCOP(=S)(OCC)ON=C(C#N)C1=CC=CC=C1
Isomeric SMILES
CCOP(=S)(OCC)O/N=C(\C#N)/C1=CC=CC=C1
International Chemical Identifier key (InChIKey)
ATROHALUCMTWTB-WYMLVPIESA-N
International Chemical Identifier (InChI)
InChI=1S/C12H15N2O3PS/c1-3-15-18(19,16-4-2)17-14-12(10-13)11-8-6-5-7-9-11/h5-9H,3-4H2,1-2H3/b14-12+
2D structure diagram/image available?
Yes
Cambridge Crystallographic Data Centre diagrams
Common Name Relationship Link
chlorphoxim Variant
General status
Veterinary substance type
Ectoparasitic agent
Other bioactivity & uses
Disinfectant
Substance groups
Organophosphate insecticide; Organophosphate acaricide; Organothiophosphate insecticide; Organothiophosphate acaricide
Minimum active substance purity
-
Known relevant impurities
-
Substance origin
Synthetic
Mode of action
Non-systemic with contact and stomach action. Short activity period. Acetylcholinesterase (AChE) inhibitor.
Molecular targets
[Cholinesterase, Inhibitor]
CAS RN
14816-18-3
EC number
238-887-3
CIPAC number
364
US EPA chemical code
598800
PubChem CID
9570290
CLP index number
015-100-00-X
Therapeutic Class
Antiparasitic products, insecticides & repellents: Organophosphorus compounds
ATCvet Code
QP53AF01
Controlled Drug?
No
Regulation 37/2010 MRL Classification
-
Molecular mass
298.3
PIN (Preferred Identification Name)
-
IUPAC name
O,O-diethyl α-cyanobenzylideneaminooxyphosphonothioate
CAS name
4-ethoxy-7-phenyl-3,5-dioxa-6-aza-4-phosphaoct-6-ene-8-nitrile 4-sulphide
Other status information
OSPAR soc
Relevant Environmental Water Quality Standards
-
Physical state
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)
1.5
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)
250000
L2 L = Pesticide manuals and hard copy reference books / other sources
2 = Unverified data of unknown source
Xylene		 -
250000
L2 L = Pesticide manuals and hard copy reference books / other sources
2 = Unverified data of unknown source
Dichloromethane		 -
250000
L2 L = Pesticide manuals and hard copy reference books / other sources
2 = Unverified data of unknown source
Acetone		 -
136000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
n-Heptane		 -
Melting point (°C)
5
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 -
Boiling point (°C)
Decomposes on distillation
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
2.40 X 1003 Calculated -
Log P
3.38
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 High
Fat solubility of residues
Solubility
Soluble
A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications )
5 = Verified data used for regulatory purposes
 -
Data type
Regulatory data - observed in metabolism and farm animal feeding studies
A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications )
5 = Verified data used for regulatory purposes
 -
Density (g ml⁻¹)
1.18
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)
2.1
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 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)
4.18 X 10-01
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 Moderately 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)
6
W4 W = French database provided by ARVALIS-Institut du Végétal. Dataset no longer available.
4 = Verified data
 Non-persistent
DT₅₀ (lab at 20 °C)
- - -
DT₅₀ (field)
- - -
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
7.2
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 Non-persistent
Note
pH sensitive: DT₅₀ 26.7 days at pH 4, 3.1 days at pH 9, all at 22 °C
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)
- - -
Koc (mL g⁻¹)
-
Notes and range
-
Freundlich
Kf (mL g⁻¹)
33.33
R4 R = Peer reviewed scientific publications
4 = Verified data
 Slightly mobile
Kfoc (mL g⁻¹)
1148
1/n
1.03
Notes and range
Kf range 27.0-44.0 (802 for peat) mL g⁻¹, Kfoc range 997-1243 (1333 for peat) mL g⁻¹, 1/n - no data, Soils=4
pH sensitivity
-
Fate indices
Property
Value
Source; quality score; and other information
Interpretation
GUS leaching potential index
0.73 Calculated Low leachability
Bio-concentration factor
BCF (l kg⁻¹)
1610
R3 R = Peer reviewed scientific publications
3 = Unverified data of known source
Whole body		 Threshold for concern
CT₅₀ (days)
Not available -
Known soil metabolites
Metabolite
Major/Minor fraction
Estimated maximum occurrence fraction
Notes
chlorphoxim (Ref: OMS 1197)
- - -
Known groundwater metabolites

None

Other known metabolites

None

ECOTOXICOLOGY
Terrestrial ecotoxicology
Property
Value
Source; quality score; and other information
Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
113
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)
-
L2 L = Pesticide manuals and hard copy reference books / other sources
2 = Unverified data of unknown source
Rat 2 yr		 -
(ppm diet)
> 15 -
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)
- - -
Birds - Acute LD₅₀ (mg kg⁻¹)
- - -
Birds - Short term dietary (LC₅₀/LD₅₀)
- - -
Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)
- - -
Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)
> 40.4
R4 R = Peer reviewed scientific publications
4 = Verified data
Eisenia foetida		 Moderate
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)
> 0.22
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Lepomis macrochirus		 Moderate
Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)
- - -
Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
> 0.414
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
Danio rerio		 Moderate
Temperate Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
0.00081
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)
- - -
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)
< 0.1
P3 P = Other non-EU, UK or US Governments and Regulators
3 = Unverified data of known source
Anabaena variabilis 5 day		 Moderate
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)
113
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)
5000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat		 -
Mammals - Inhalation LC₅₀ (mg l⁻¹)
4.0
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
Phosmet is rapidly absorbed, distributed, and eliminated in mammals with ~75% lost in urine
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
 -
Health issues
Specific human health issues
Carcinogen
Genotoxic
Endocrine disruptor
No data found
A3 A = Chromosome aberration (EFSA database)
3 = Negative
;
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
✓Yes, known to cause a problem
Respiratory tract irritant Skin irritant Skin sensitiser
?Possibly, status not identified
✓Yes, known to cause a problem
✓Yes, known to cause a problem
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
Flammable
CLP classification 2013
Health: H302, H317, H361f
Environment: H400, H410
WHO Classification
II (Moderately hazardous)
UN Number
-
Waste disposal & packaging
-
Shelf-life, storage, stability and reactivity
-
TRANSLATIONS
Language
Name
English
phoxim
French
phoxime
German
Phoxim
Danish
phoxim
Italian
foxim
Spanish
foxim
Greek
phoxim
Polish
foksim
Swedish
foxim
Hungarian
-
Dutch
foxim
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