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Naftalofos (Ref: ENT 25567)
Last updated: 24/07/2024
(Also known as: BAY S-940; naphthalophos)
GENERAL INFORMATION
Description
An obsolete organophosphate insecticide and veterinary anthelmintic drug
Availability status
-
Introduction & key dates
-
Examples of veterinary uses
Once used to treat parasitic nematodes
Examples of species treated
Sheep; Goats; Cattle; Rainbow trout
Approval status
VMR 2013/2033 approval status (GB/UK)
Not approved
EU Regulatory approval status
Not approved
Chemical structure
Isomerism
None
Chemical formula
C₁₆H₁₆NO₆P
Canonical SMILES
CCOP(=O)(OCC)ON1C(=O)C2=CC=CC3=C2C(=CC=C3)C1=O
Isomeric SMILES
-
International Chemical Identifier key (InChIKey)
QNSIFYWAPWSAIJ-UHFFFAOYSA-N
International Chemical Identifier (InChI)
InChI=1S/C16H16NO6P/c1-3-21-24(20,22-4-2)23-17-15(18)12-9-5-7-11-8-6-10-13(14(11)12)16(17)19/h5-10H,3-4H2,1-2H3
2D structure diagram/image available?
Yes
General status
Veterinary substance type
Anthelmintic
Substance groups
Organophosphorus insecticide; Meta-diamide insecticide; Heterotricyclic compound
Minimum active substance purity
>98%
Known relevant impurities
-
Substance origin
Synthetic
Mode of action
Acetylcholinesterase (AChE) inhibitor.
Molecular targets
[Cholinesterase, Inhibitor]
CAS RN
1491-41-4
EC number
216-078-6
CIPAC number
None allocated
US EPA chemical code
-
PubChem CID
15148
CLP index number
No data found
Therapeutic Class
Antiparasitic products, insecticides & repellents: Anthelmintics, Organophosphorus compounds
ATCvet Code
QP52AB06
Controlled Drug?
No
Regulation 37/2010 MRL Classification
-
Molecular mass
349.27
PIN (Preferred Identification Name)
1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl diethyl phosphate
IUPAC name
2-[(diethoxyphosphoryl)oxy]-1H-benzo[de]isoquinoline-1,3(2H)-dione
CAS name
2-[(diethoxyphosphinyl)oxy]-1H-benz[de]isoquinoline-1,3(2H)-dione
Other status information
-
Relevant Environmental Water Quality Standards
-
Physical state
Solid
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)
- - -
Solubility - In organic solvents at 20 °C (mg l⁻¹)
- - -
Melting point (°C)
174
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
 -
Boiling point (°C)
487
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
 -
Degradation point (°C)
- - -
Flashpoint (°C)
248
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
 -
Octanol-water partition coefficient at pH 7, 20 °C
P
- - -
Log P
- - -
Fat solubility of residues
Solubility
- - -
Data type
- - -
Density (g ml⁻¹)
1.41
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
 -
Dissociation constant pKa) at 25 °C
- - -
-
Vapour pressure at 20 °C (mPa)
- - -
Henry's law constant at 25 °C (Pa m³ mol⁻¹)
- - -
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
1.612
Q3 Q = Miscellaneous data from online 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)
- - -
DT₅₀ (lab at 20 °C)
- - -
DT₅₀ (field)
- - -
DT₉₀ (lab at 20 °C)
- - -
DT₉₀ (field)
- - -
Note
-
Manure DT₅₀ (days)
- - -
Aqueous photolysis DT₅₀ (days) at pH 7
Value
- - -
Note
-
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7
Value
- - -
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)
- - -
Koc (mL g⁻¹)
-
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
- - -
Bio-concentration factor
BCF (l kg⁻¹)
- - -
CT₅₀ (days)
- -
Known metabolites

None

ECOTOXICOLOGY
Terrestrial ecotoxicology
Property
Value
Source; quality score; and other information
Interpretation
Mammals - Acute oral LD₅₀ (mg kg⁻¹)
70
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
Rat		 High
Mammals - Short term dietary NOEL
(mg kg⁻¹)
- - -
(ppm diet)
- -
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)
- - -
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)
- - -
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)
70
Q3 Q = Miscellaneous data from online sources
3 = Unverified data of known source
Rat		 High
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
- - -
Mammals - Inhalation LC₅₀ (mg l⁻¹)
- - -
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
- - -
Exposure Routes
Public
-
Occupational
-
Mammalian dose elimination route and rate
- - -
Health issues
Specific human health issues
Carcinogen
Genotoxic
Endocrine disruptor
No data found No data 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 No data found No data found
Eye irritant Phototoxicant  
No data found No data found  
General human health issues
Highly toxic
May be fatal in contact with skin
Handling issues
Property
Value and interpretation
General
Not explosive or oxidising
IMDG Transport Hazard Class 6.1
CLP classification 2013
Health: H301, H310
WHO Classification
Not listed (Not listed)
UN Number
UN3464
Waste disposal & packaging
Packaging Group I (great danger)
Shelf-life, storage, stability and reactivity
-
TRANSLATIONS
Language
Name
English
naftalofos
French
naftalofos
German
-
Danish
-
Italian
-
Spanish
-
Greek
-
Polish
-
Swedish
-
Hungarian
-
Dutch
-
Norwegian
-
Record last updated: 24/07/2024
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