Azinphos-ethyl (Ref: BAY 16259)	Last updated: 17/12/2020
(Also known as: azinphosethyl; triazotion; azinphos ethyl; R1513; ethyl gusathion)

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SUMMARY

Azinphos-ethyl is an organophosphate insecticide that is not approved for use in the EU. 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.

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	Unknown
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

Also used in

Also used in	-

Chemical structure

Isomerism	-
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 group	Organophosphate
Minimum active substance purity	-
Known relevant impurities	-
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
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
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

Formulations

Property	Value
Example manufacturers & suppliers of products using this active now or historically	Gusthion A Gusthion H Cotnion-ethyl
Example products using this active	Bayer Makhteshim-Agan
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 / IPCS INCHEM (ChemID; IPCS INCHEM ) 3 = Unverified data of known source	-
Degradation point (°C)		-	-	-
Flashpoint (°C)		Not expected to self ignite; Not highly flammable	V3 V = ChemID online databases / IPCS INCHEM (ChemID; IPCS INCHEM ) 3 = Unverified data of known source	-
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
Bulk 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 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 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 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	-

Key metabolites

Metabolite	Formation medium	Estimated maximum occurrence fraction	1107/2009 relevancy
desethyl azinphos-ethyl	Soil	-	-
sulfonmethylbenzamid	Soil	-	-

ECOTOXICOLOGY

Property		Value	Source; quality score; and other information	Interpretation
Bio-concentration factor	BCF (l kg⁻¹)	101	Q2 Q = Miscellaneous internet resources 2 = Unverified data of unknown source Estimated	Threshold for concern
	CT₅₀ (days)	Not available		-
Mammals - Acute oral LD₅₀ (mg kg⁻¹)		12	F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents (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)		-	-	-
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)		-	-	-
Non-target plants		-	-	-
		-	-	-
Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)		-	-	-
Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)		-	-	-
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)	-	-	-
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 pollinators (1)	Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)	-	-	-
	Mode of exposure	-
Other pollinators (2)	Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)	-	-	-
	Mode of exposure	-
Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)		-	-	-
Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)		-	-	-
Other soil macro-organisms	Acute LC₅₀ (mg kg⁻¹)	-	-	-
	Chronic NOEC (mg kg⁻¹)	-	-	-
Other arthropod (1)	LR₅₀ g ha⁻¹	-	-	-
	% Effect	-	-	-
Other arthropod (2)	LR₅₀ g ha⁻¹	-	-	-
	% Effect	-	-	-
Soil micro-organisms		-	-	-
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 (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		-	-	-
ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)		0.03	Q3 Q = Miscellaneous internet resources 3 = Unverified data of known source as ug/day India	-
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
	Notes	-
Drinking Water Standards		-	-	-
Drinking Water MAC (μg l⁻¹)		-	-	-

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 ; E0 E = Unspecified genotoxicity type (miscellaneous data source) 0 = No data 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 Transport Code is 6.1
CLP classification 2013	Health: H300, H311 Environment: H400, H410
EC Risk Classification	T+ - Very toxic: R28 T - Toxic: R24 N - Dangerous for the environment: R50, R53
EC Safety Classification	S1/2, S28, S45, S61, S36/37, S60
WHO Classification	Ib (Highly hazardous / Highly hazardous)
UN Number	Active 2783, liquid products usually 3018
Waste disposal & packaging	-

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

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Record last updated:	17/12/2020
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