Acetamiprid

Acetamiprid	Last updated: 22/08/2024
(Also known as: ethanimidamide; NI-25)

SUMMARY

Acetamiprid is an insecticide that is used to control sucking and chewing pests. It is highly soluble in water and is volatile. Based on its chemical properties it would not be expected to leach to groundwater. It is not persistence in soil systems but may be very persistent in aquatic systems under certain conditions. It has a moderate mammalian toxicity and it has a high potential for bioaccumulation. Acetamiprid is a recognised irritant. It is highly toxic to birds and earthworms and moderately toxic to most aquatic organisms.

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 Moderate alert: Drainflow: Moderately mobile	Ecotoxicity High alert: Birds acute ecotoxicity: High; Birds chronic ecotoxicity: High; Earthworms acute ecotoxicity: High	Human health Moderate alert: Mammals acute toxicity: Moderate; Mammals chronic toxicity: Moderate; Reproduction/development effects

GENERAL INFORMATION

Description

A pyridylmethylamine insecticide used for the control of Hemiptera spp. especially aphids.

Example pests controlled

Aphids; Thrips; Mirids; Spider mites; Whiteflies; European pine sawflies; Leaf miners; Leaf hoppers; Vine weevil; Ants

Example applications

Leafy Vegetables; Fruiting Vegetables; Fruit including citrus, apples, pears, grapes; Cotton; Ornamental Plants and Flowers

Efficacy & activity

Availability status

Current

Introduction & key dates

1995, first introduced Japan

GB regulatory status

GB COPR regulatory status

Approved

Date COPR inclusion expires

28/02/2033

GB LERAP status

Check label - may vary with formulation

EC Regulation 1107/2009 (repealing 91/414)

EC Regulation 1107/2009 status

Approved

Dossier rapporteur/co-rapporteur

Netherlands/Spain

Date EC 1107/2009 inclusion expires

28/02/2033

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

Australia, USA, Egypt, Morroco

Chemical structure

Isomerism

There are 2 isomeric forms in acetamiprid with E and Z-configurations of the cyano-imino group

Chemical formula

C₁₀H₁₁ClN₄

Canonical SMILES

CC(=NC#N)N(C)CC1=CN=C(C=C1)Cl

Isomeric SMILES

International Chemical Identifier key (InChIKey)

WCXDHFDTOYPNIE-RIYZIHGNSA-N

International Chemical Identifier (InChI)

InChI=1S/C10H11ClN4/c1-8(14-7-12)15(2)6-9-3-4-10(11)13-5-9/h3-5H,6H2,1-2H3/b14-8+

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
acetamiprid	Unstated isomer

General status

Pesticide type

Insecticide

Substance groups

Neonicotinoid insecticide; Pyridylmethylamine neonicotinoid insecticide

Minimum active substance purity

990 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Systemic with translaminar activity having both contact and stomach action. Nicotinic acetylcholine receptor (nAChR) channel blocker.

CAS RN

135410-20-7

EC number

603-921-1

CIPAC number

649

US EPA chemical code

099050

PubChem CID

213021

CLP index number

608-032-00-2

Molecular mass

222.67

PIN (Preferred Identification Name)

(1E)-N-[(6-chloropyridin-3-yl)methyl]-N'-cyano-N-methylethanimidamide

IUPAC name

(E)-N1-[(6-chloro-3-pyridyl)methyl]-N2-cyano-N1-methylacetamidine

CAS name

(1E)-N-[(6-chloro-3-pyridinyl)methyl]-N'-cyano-N-methylethanimidamide

Other status information

NOTE ban or usage restriction may be in place for use on flowering crops in some Member States

Relevant Environmental Water Quality Standards

Herbicide Resistance Class (HRAC MoA class)

Not applicable

Herbicide Resistance Class (WSSA MoA class)

Not applicable

Insecticide Resistance Class (IRAC MoA class)

Fungicide Resistance Class (FRAC MOA class)

Not applicable

Examples of recorded resistance

Acarus siro, Bemisia tabaci, Leptinotarsa decemlineata

Physical state

A white to pale yellow crystalline solid

Formulations

Property

Value

Example manufacturers & suppliers of products using this active now or historically

AgroCare
Certis
Aventis
Nisso Chemical Europe
Nippin Soda
BOC Sciences
Imtrade Vader 225

Example products using this active

Acetamiprid WP
Gazelle
Mospilan 20 SG
Antilop SG
Assail
Acetamiprid Gel Bait Station for Ants
Mospilan
Imtrade Australia Pty Ltd

Formulation and application details

Usually formulated as soluble granules for spray application

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

2950

High

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

6.54

Hexane

200000

Chloroform

200000

Dichloromethane

200000

Acetone

Melting point (°C)

98.9

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

200

Flashpoint (°C)

166.9

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

6.31 X 10⁰⁰

Calculated

Log P

0.8

Low

Fat solubility of residues

Solubility

Insoluble

Data type

Regulatory data

Density (g ml⁻¹)

1.33

Dissociation constant pKa) at 25 °C

0.7

Weak base

Vapour pressure at 20 °C (mPa)

1.0 X 10^-03

at 25 °C

Low volatility

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

5.30 X 10^-08

Non-volatile

Volatilisation as max % of applied dose lost

From plant surface

24 hr

Volatilisation is not considered critical for air pollution

From soil surface

Negligible

24 hr

Maximum UV-vis absorption L mol⁻¹ cm⁻¹

Neutral solution: 247nm = 19700, 217nm = 12100

Surface tension (mN m⁻¹)

70.9

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Not readily biodegradeable

Soil degradation (days) (aerobic)

DT₅₀ (typical)

1.6

Non-persistent

DT₅₀ (lab at 20 °C)

1.6

Non-persistent

DT₅₀ (field)

Non-persistent

DT₉₀ (lab at 20 °C)

8.8

Non-persistent

DT₉₀ (field)

20.2

DT₅₀ modelling endpoint

Note

EU dossier Lab studies DT₅₀ range 0.8-5.4 days, DT₉₀ range 2.8-67.3 days, field studies (2015 RAR) DT₅₀ range 0.8-4.7 days, DT₉₀ range 2.7-28 days; Other sources: 2-20 days

Dissipation rate RL₅₀ (days) on plant matrix

Value

6.3

Note

Published literature RL₅₀ range 3.0-12.3 days, 3 field crops, various matrices, n=3

Dissipation rate RL₅₀ (days) on and in plant matrix

Value

6.3

Note

Published literature RL₅₀ range 1.2-22.8 days, 18 field & undercover grown crops, various matrices, n=26

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Stable

Note

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

Value

Stable

Note

Stable pH 4 to pH 7 at temps 22-45 °C. Degradation does occur at higher pHs and elevated temps e.g. DT₅₀ 420 days at pH 9, 25 °C, 13 days pH9, 45 °C

Water-sediment DT₅₀ (days)

Water phase only DT₅₀ (days)

4.7

Moderately fast

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

[Pear homogenate: No observed residue decay @ <=20 DegC after 7 days; Lab study]

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d (mL g⁻¹)

Moderately mobile

K_oc (mL g⁻¹)

200

Notes and range

Freundlich

K_f (mL g⁻¹)

1.58

Moderately mobile

K_foc (mL g⁻¹)

106.5

¹/_n

0.86

Notes and range

EU dossier (2015 RAR) K_f range 0.6-3.13 mL g⁻¹, K_foc range 71.38-138.39 mL g⁻¹, ¹/_n range 0.825-0.807, Soils=5

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

0.94

Calculated

Low leachability

SCI-GROW groundwater index (μg l⁻¹) for a 1 kg ha⁻¹ or 1 l ha⁻¹ application rate

Value

2.16 X 10^-03

Calculated

Note

Potential for particle bound transport index

Low

Calculated

Potential for loss via drain flow

Moderately mobile

Calculated

Photochemical oxidative DT₅₀ (hrs) as indicator of long-range air transport risk

3.36

Calculated using the Atkinson method, 12 hr

Below the level of concern for long-range air transport

Bio-concentration factor

BCF (l kg⁻¹)

Low risk

Based on LogP < 3

Low risk

CT₅₀ (days)

No data

Known soil metabolites

Metabolite

Major/Minor fraction

$Click here for further information on Major/Minor fraction$

Estimated maximum occurrence fraction

Notes

(E)-N2-carbamoyl-N1-(6-chloro-3-pyridyl)methyl-N2-cyano-N1-methylacetamidine (Ref: IM-1-2)

Major fraction

0.549

6-chloronicotinic acid (Ref: IC-0)

Major fraction

0.113

N-(6-chloropyridin-3-ylmethyl)-N-methyl-acetamidine (Ref: IM1-5)

Major fraction

0.200

N-methyl(6-chloro-3-pyridyl)methylamine (Ref: IM-1-4)

Major fraction

0.720

Known groundwater metabolites

Metabolite

EC SANCO/221/2000 relevancy

ADI (mg kg⁻¹ bodyweight day⁻¹)

WHO drinking water guidance value (μg L⁻¹ day⁻¹)

N-(6-chloropyridin-3-ylmethyl)-N-methyl-acetamidine (Ref: IM-1-5)

Relevant

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

N-{(6-chloro-3-pyridyl)methyl}-N-methylacetamide (Ref: IM-1-3)
Note: Toxic

Animal; Water (Hydrolysis)

N-[(6-chloro-3-pyridyl)methyl]acetamide (Ref: IM-2-3)
Note: Toxic

Animal

6-chloro-pyridilmethyl alcohol (Ref: IM-0)
Note: Toxic

Animal; Plant

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

146

Rat

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

Rat

High

(ppm diet)

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

> 51

Rat Reproductive NOAEL

Moderate

Birds - Acute LD₅₀ (mg kg⁻¹)

Anas platyrhynchos

High

Birds - Short term dietary (LC₅₀/LD₅₀)

> 741 mg kg bw⁻¹ day⁻¹

Colinus virginianus

Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)

9.5

Anas platyrhynchos NOAEL

High

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

Eisenia foetida

High

Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)

1.26

Eisenia foetida

Moderate

Soil micro-organisms

Nitrogen mineralisation: No significant adverse effect
Carbon mineralisation: No significant adverse effect

Dose: 0.2 kg ha⁻¹

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

0.27

Folsomia candida

Non-target plants

Honeybees (Apis spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

8.09

Apis mellifera

Moderate

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

14.53

Apis mellifera

Moderate

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)

> 100

Bombus terrestris

Low

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

22.2

Bombus terrestris

Moderate

Literature DT₅₀ 48hr values for B. hyprocrita = >0.0019 µg bee⁻¹, B. ignitus = > 0.005 µg bee⁻¹ & B. patagiatu = > 0.005 µg bee⁻¹

Mason bees (Osmia spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

1.72

Osmia bicornis

Moderate

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) as Mortality, Contact LD₅₀ mg l⁻¹

> 0.05

Coccinella septempunctata

Beneficial insects (Lacewings) as Mortality, Contact LC₅₀ ug/mL

> 0.65

Chrysoperla carnea Larva

Beneficial insects (Parasitic wasps) as Mortality LR₅₀ kg ha⁻¹

0.002

Aphidius rhopalosiphi

Beneficial insects (Predatory mites) as Mortality LR₅₀ kg ha⁻¹

0.03

Typhlodromus pyri

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)

> 100

Oncorhynchus mykiss

Low

Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)

19.2

Pimephales promelas 32 day

Low

Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 8.59

Danio rerio

Moderate

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

49.8

Daphnia magna

Moderate

Temperate Freshwater Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)

Daphnia magna

Moderate

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

> 33.5

Ceriodaphnia dubia

Moderate

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)

2.8

Chironomus dilutus

Moderate

Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)

0.005

Chironomus riparius

High

Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)

Aquatic plants - Acute 7 day EC₅₀, biomass (mg l⁻¹)

Lemna gibba

Moderate

Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)

> 98.3

Scenedesmus subspicatus

Low

Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)

Mesocosm study data

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)

146

Rat

Moderate

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

2000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 1.15

Rat

Other Mammal toxicity endpoints

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

0.025

ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)

0.025

Rat SF=100

AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)

0.025

Dermal penetration studies (%)

15.9-33.7

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Minimal risk from dietary exposure
Source: US EPA/EU

Occupational

Occupational exposure may occur through inhalation and dermal contact. Operator health should be monitored

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

There is some evidence that acetamiprid is linked to human infertility
Does not appear to have specific target organ toxicity

Handling issues

Property

Value and interpretation

General

Combustable
Not expected to auto-ignite
Not explosive or oxidising
IMDG Transport Hazard Class 6.1

CLP classification 2013

Health: H302
Environment: H412

WHO Classification

II (Moderately hazardous)

UN Number

UN2811

Waste disposal & packaging

Packaging Group II (moderate danger)

Shelf-life, storage, stability and reactivity

Limited shelf-life. Store at 0-6 DegC

TRANSLATIONS

Language

Name

English

acetamiprid

French

acetamipride

German

Acetamiprid

Danish

acetamiprid

Italian

acetamiprid

Spanish

acetamiprid

Greek

Polish

acetamipryd

Swedish

acetamiprid

Hungarian

acetamiprid

Dutch

acetamiprid

Norwegian

acetamiprid

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