Azinphos-ethyl (Ref: BAY 16259)

Azinphos-ethyl (Ref: BAY 16259)	Last updated: 04/03/2022
(Also known as: azinphosethyl; triazotion; azinphos ethyl; R1513; ethyl gusathion)

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

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

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; 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)

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

azinphos-methyl

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

Low

Solubility - In organic solvents at 20 °C (mg l⁻¹)

3500

n-Hexane

35000

Isopropanol

1000000

Dichloromethane

1000000

Toluene

Melting point (°C)

Boiling point (°C)

111

Degradation point (°C)

Flashpoint (°C)

Octanol-water partition coefficient at pH 7, 20 °C

1.51 X 10⁰³

Calculated

Log P

3.18

High

Density (g ml⁻¹)

1.28

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

0.32

Low volatility

Henry's law constant at 25 °C (Pa m³ mol⁻¹)

3.05 X 10^-06

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)

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

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

Fast

Note

Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7

Value

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

K_d

Slightly mobile

K_oc

1500

Notes and range

Other source K_oc 1700 mL g⁻¹ estimate (CA2)

Freundlich

K_f

K_foc

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

Estimated

Threshold for concern

CT₅₀ (days)

Not available

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

desethyl azinphos-ethyl

Soil

sulfonmethylbenzamid

Soil

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

Rat

High

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat 2 year

(ppm diet)

Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)

Birds - Acute LD₅₀ (mg kg⁻¹)

> 12.5

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

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 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

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

Oncorhynchus mykiss

High

Fish - Chronic 21 day NOEC (mg l⁻¹)

Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

0.0002

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

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)

Rat

High

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

500

Rat 24hr

Mammals - Inhalation LC₅₀ (mg l⁻¹)

0.15

Rat

Other Mammal toxicity endpoints

ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)

0.03

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

Great Britain

GB MRL Register

Notes

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

Mammalian dose elimination route and rate

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

No further information available

Handling issues

Property

Value and interpretation

General

IMDG Transport Code is 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

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

Record last updated:	04/03/2022
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