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Azinphos-ethyl (Ref: BAY 16259)
(Also known as: azinphosethyl; triazotion; azinphos ethyl; R1513; ethyl gusathion; Bayer 17147)
SUMMARY
Azinphos-ethyl is an organophosphate insecticide used to control sucking and chewing pests. It has a low aqueous solubility, relatively volatile and is not expected to leach to groundwater. It may be moderately persistent in some soil systems but is not expected to be persistent in water. It is toxic to mammals and there is also concern regarding its potential to bioaccumulate. It is a neurotoxicant and an acetyl cholinesterase inhibitor. Azinphos-ethyl is highly toxic to birds, fish and aquatic invertebrates. It is moderately toxic to honeybees.
Data alerts

The following alerts are based on the data in the tables below. An absence of an alert does not imply the substance has no implications for human health, biodiversity or the environment but just that we do not have the data to form a judgement.

Environmental fate Ecotoxicity Human health
Environmental fate
High alert:
Potential for particle bound transport: High
Warning:
Significant data are missing
Ecotoxicity
High alert:
Birds acute ecotoxicity: High; Fish acute ecotoxicity: High; Daphnia acute ecotoxicity: High
Human health
High alert:
Mammals acute toxicity: High; Acetyl cholinesterase inhibitor; Neurotoxicant
GENERAL INFORMATION
Description
A benzotriazine organothiophosphate insecticide and organothiophosphate acaricide for the control of sucking and chewing pests
Example pests controlled
Spider mites; Aphids; Caterpillers; Potato bugs including Colorado beetles; Oat mites; Tocks
Example applications
Cotton; Rice; Tobacco; Melons; Tomatoes; Potatoes; Hops; Beet crops; Citrus; Soybeans; Apples
Efficacy & activity
-
Availability status
-
Introduction & key dates
1955
UK regulatory status
UK COPR regulatory status
Not approved
Date COPR inclusion expires
Expired
UK LERAP status
No UK approval for use
EC Regulation 1107/2009 (repealing 91/414)
EC Regulation 1107/2009 status
Not approved
Dossier rapporteur/co-rapporteur
Germany
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
                 
Approved for use (✓) under EC 1107/2009 by Mutual Recognition of Authorisation and/or national regulations in the following EEA countries
ISIceland
NONorway
                 
Additional information
Also used in
-
Chemical structure
Isomerism
None
Chemical formula
C₁₂H₁₆N₃O₃PS₂
Canonical SMILES
CCOP(=S)(OCC)SCN1C(=O)C2=CC=CC=C2N=N1
Isomeric SMILES
No data
International Chemical Identifier key (InChIKey)
RQVGAIADHNPSME-UHFFFAOYSA-N
International Chemical Identifier (InChI)
InChI=1S/C12H16N3O3PS2/c1-3-17-19(20,18-4-2)21-9-15-12(16)10-7-5-6-8-11(10)13-14-15/h5-8H,3-4,9H2,1-2H3
2D structure diagram/image available?
Yes
Cambridge Crystallographic Data Centre diagrams
Common Name Relationship Link
azinphos-ethyl -
General status
Pesticide type
Insecticide, Acaricide
Substance groups
Organophosphate Insecticide; Organophosphate acaricide; Organothiophosphate insecticide; Organothiophosphate acaricide
Minimum active substance purity
-
Known relevant impurities
FAO: acetone insolubles
Substance origin
Synthetic
Mode of action
Non-systemic, contact and stomach action. Cholinesterase inhibitor. Ovicidal.
CAS RN
2642-71-9
EC number
220-147-6
CIPAC number
485
US EPA chemical code
058002
PubChem CID
17531
CLP index number
015-056-00-1
Molecular mass
345.38
PIN (Preferred Identification Name)
O,O-diethyl S-[(4-oxo-1,2,3-benzotriazin-3(4H)-yl)methyl] phosphorodithioate
IUPAC name
S-3,4-dihydro-4-oxo-1,2,3-benzotriazin-3-ylmethyl O,O-diethyl phosphorodithioate
CAS name
O,O-diethyl S-((4-oxo-1,2,3-benzotriazin-3(4H)-yl)methyl) phosphorodithioate
Other status information
Severe Marine Pollutant; Chemical subject to PIC regulations; PAN Bad Actor Chemical; Subject to the provisions of the UK Poisons Act 1972
Relevant Environmental Water Quality Standards
-
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
Culex pipiens pipiens, Myzus persicae, Phorodon humuli
Physical state
Colourless needle-like crystals
Related substances & organisms
Formulations
Property
Value
Example manufacturers & suppliers of products using this active now or historically
  • Bayer
  • Makhteshim-Agan
Example products using this active
  • Gusthion A
  • Gusthion H
  • Cotnion-ethyl
  • Guthion M-E 4 Concentrate
Formulation and application details
Available in a variety of formulations including dusts, emulsifiable concentrates, ULVs and wettable powders.
ENVIRONMENTAL FATE
Property
Value
Source; quality score; and other information
Interpretation
Solubility - In water at 20 °C (mg l⁻¹)
4.5
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)
3500
L2 L = Pesticide manuals and hard copy reference books / other sources
2 = Unverified data of unknown source
n-Hexane		 -
35000
L2 L = Pesticide manuals and hard copy reference books / other sources
2 = Unverified data of unknown source
Isopropanol		 -
1000000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Dichloromethane		 -
1000000
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Toluene		 -
Melting point (°C)
50
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
 -
Boiling point (°C)
111
V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID )
3 = Unverified data of known source
 -
Degradation point (°C)
- - -
Flashpoint (°C)
- - -
Octanol-water partition coefficient at pH 7, 20 °C
P
1.51 X 1003 Calculated -
Log P
3.18
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)
1.28
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)
0.32
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)
3.05 X 10-06
L3 L = Pesticide manuals and hard copy reference books / other sources
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)
50
L2 L = Pesticide manuals and hard copy reference books / other sources
2 = Unverified data of unknown source
 Moderately persistent
DT₅₀ (lab at 20 °C)
- - -
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
10
R4 R = Peer reviewed scientific publications
4 = Verified data
 -
Note
Apple fruit, n=1; Apples in store RL₅₀ range 83-91 days, n=2
Aqueous photolysis DT₅₀ (days) at pH 7
Value
0.4
K4 K = Research datasets (e.g. Pandora, Demetra; these datasets no longer available). Norman Ecotoxicology database. (click here )
4 = Verified data
 Fast
Note
-
Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7
Value
13
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)
- - -
Soil adsorption and mobility
Property
Value
Source; quality score; and other information
Interpretation
Linear
Kd
-
P2 P = Other non-EU, UK or US Governments and Regulators
2 = Unverified data of unknown source
 Slightly mobile
Koc
1500
Notes and range
Other source Koc 1700 mL g⁻¹ estimate (CA2)
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
1.40 Calculated Low leachability
SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate
Value
3.46 X 10-02 Calculated -
Note
-
Potential for particle bound transport index
High Calculated -
Potential for loss via drain flow
Slightly mobile Calculated -
Bio-concentration factor
BCF (l kg⁻¹)
101
Q2 Q = Miscellaneous data from online sources
2 = Unverified data of unknown source
Estimated		 Threshold for concern
CT₅₀ (days)
Not available -
Known soil metabolites
Metabolite
Major/Minor fraction
Estimated maximum occurrence fraction
Notes
desethyl azinphos-ethyl
- - -
sulfonmethylbenzamid
- - -
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)
12
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
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)
2 -
Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)
- - -
Birds - Acute LD₅₀ (mg kg⁻¹)
> 12.5
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Coturnix japonica		 High
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)
> 1.39
R4 R = Peer reviewed scientific publications
4 = Verified data
 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
- - -
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
Fish - Acute 96 hour LC₅₀ (mg l⁻¹)
0.08
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Oncorhynchus mykiss		 High
Fish - Chronic 21 day NOEC (mg l⁻¹)
- - -
Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)
0.0002
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)
- - -
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
- - -
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)
12
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
Rat		 High
Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)
500
L2 L = Pesticide manuals and hard copy reference books / other sources
2 = Unverified data of unknown source
Rat 24hr		 -
Mammals - Inhalation LC₅₀ (mg l⁻¹)
0.15
L3 L = Pesticide manuals and hard copy reference books / other sources
3 = Unverified data of known source
Rat		 -
Other Mammal toxicity endpoints
Interperitoneal LD₅₀ < 4.4 mg kg⁻¹
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
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
Consumer exposure should be low or non-existent since azinphos ethyl is no longer produced or used in most of the developed world
Occupational
Occupational exposure should be low or non-existent since azinphos ethyl is no longer produced or used in most of the developed world
MRLs
European
EU MRL pesticide database 
Great Britain
GB MRL Register 
Notes
-
Drinking Water Standards
- - -
Drinking Water MAC (μg l⁻¹)
- - -
Mammalian dose elimination route and rate
Eliminated in the faeces (~60%) and urine (~40%)
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
 -
Health issues
Specific human health issues
Carcinogen
Genotoxic
Endocrine disruptor
XNo, known not to cause a problem
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
;
E3 E = Unspecified genotoxicity type (miscellaneous data source)
3 = Negative
 No data found
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
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
No further information available
Handling issues
Property
Value and interpretation
General
IMDG TransportHazard Class 6.1
Not expected to autoignite; Not highly flammable
CLP classification 2013
Health: H300, H311
Environment: H400, H410
WHO Classification
Ib (Highly hazardous)
UN Number
UN2783
Waste disposal & packaging
-
Shelf-life, storage, stability and reactivity
-
TRANSLATIONS
Language
Name
English
azinphos-ethyl
French
azinphos-ethyl
German
Azinphos-ethyl
Danish
azinphos-ethyl
Italian
azinfos-etile
Spanish
azinfos-etil
Greek
azinphos-ethyl
Polish
azinofos etylowy
Swedish
-
Hungarian
azinphos-ethyl
Dutch
azinfos-ethyl
Norwegian
-
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