Imidacloprid (Ref: BAY NTN 33893)

Imidacloprid (Ref: BAY NTN 33893)	Last updated: 05/07/2020
(Not known by any other names)

SUMMARY

Imidacloprid is an insecticide approved for use in the EU with certain restrictions for flowering crops. It is highly soluble, non-volatile and persistent in soil. It is moderately mobile. It has a low risk of bioaccumulating. It is highly toxic to birds and honeybees. Moderately toxic to mammals and earthworms. It is non-toxic to fish.

GENERAL INFORMATION

Description

A chloronicotine insecticide used to control sucking and soil insects. Also used as a flea treatment for domestic pets.

Example pests controlled

Plant hoppers, Aphids, Termites, Colorado bettle, Fleas, White grups, Craneflies; Crickets, Ants

Example applications

Lawns and turf; Domestic pets; Rice, Cereals; Maize; Potatoes; Sugar beet

Efficacy & activity

Availability status

Current

Introduction & key dates

1990, first reported; 1991, introduced

UK regulatory status

UK approval status

Approved

EC Regulation 1107/2009 (repealing 91/414)

EC Directive 91/414 Status

Approved

Dossier rapporteur/co-rapporteur

Germany/Netherlands

Date inclusion expires

31/07/2022

EU Candidate for substitution (CfS)

Listed in EU database

Yes

Approved for use (✓) or known to be used (#) in the following EU-27 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

Australia, USA

Chemical structure

Isomerism

Isomeric - existing as both the E- and Z- forms however many commerical products are comprised of almost entirely the (E)-isomer

Chemical formula

C₉H₁0ClN₅O₂

Canonical SMILES

C1CN(C(=N1)N[N+](=O)[O-])CC2=CN=C(C=C2)Cl

Isomeric SMILES

No data

International Chemical Identifier key (InChIKey)

YWTYJOPNNQFBPC-UHFFFAOYSA-N

International Chemical Identifier (InChI)

InChI=1S/C9H10ClN5O2/c10-8-2-1-7(5-12-8)6-14-4-3-11-9(14)13-15(16)17/h1-2,5H,3-4,6H2,(H,11,13)

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
imidacloprid	-

General status

Pesticide type

Insecticide, Veterinary substance

Substance group

Neonicotinoid

Minimum active substance purity

970 g kg⁻¹

Known relevant impurities

EU dossier - None declared

Substance origin

Synthetic

Mode of action

Systemic with contact and stomach action. Acetylcholine receptor (nAChR) agonist.

CAS RN

138261-41-3

EC number

CIPAC number

582

US EPA chemical code

129099

PubChem CID

86418

Molecular mass

255.66

PIN (Preferred Identification Name)

IUPAC name

(E)-1-(6-chloro-3-pyridylmethyl)-N-nitroimidazolidin-2-ylideneamine

CAS name

(2E)-1-((6-chloro-3-pyridinyl)methyl)-N-nitro-2-imidazolidinimine

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 Classification (HRAC)

Not applicable

Herbicide Resistance Classification (WSSA)

Not applicable

Insecticide Resistance Classification (IRAC)

Fungicide Resistance Classification (FRAC)

Not applicable

Examples of recorded resistance

Aphis gossypii, Myzus persicae, Phorodon humuli, Sogatella furcifera, Bemisia argentifolii, many others

Physical state

Colourless to cream crystalline powder depending on purity

Related substances & organisms

beta-cyfluthrin

fuberidazole

triadimenol

Formulations

Property

Value

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

Admire
Chinook Blue
Tripod Plus
Gaucho
Raxil

Example products using this active

Bayer CropScience
Makhteshim-Agan
Scotts

UK LERAP status

None

Formulation and application details

Often supplied as granules that are mixed with water and applied as a spray, used as a seed treatment or applied directly to compost. For animal use it is usually supplied as a spot-on solution.

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

610

High

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

67000

Dichloromethane

690

Toluene

100

n-Hexane

2300

2-Propanol

Melting point (°C)

144

Boiling point (°C)

Decomposes before boiling

Degradation point (°C)

230

Flashpoint (°C)

Not expected to self ignite; Not highly flammable

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

3.72 X 10⁰⁰

Calculated

Log P

0.57

Low

Bulk density (g ml⁻¹)

1.54

Dissociation constant pKa) at 25 °C

Not applicable

No dissociation

Vapour pressure at 20 °C

4.0 X 10^-07

Low volatility

Henry's law constant at 25 °C

1.7 X 10^-10

Non-volatile

GUS leaching potential index

3.69

Calculated

High leachability

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

Value

8.63 X 10^-01

Calculated

Note

Potential for particle bound transport index

Medium

Calculated

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

212nm = 13346, 270nm = 22054

Surface tension (mN m⁻¹)

72.2

at 20°C

Degradation

Property

Value

Source; quality score; and other information

Interpretation

General biodegradability

Soil degradation (days) (aerobic)

DT₅₀ (typical)

191

Persistent

DT₅₀ (lab at 20 °C)

187

Persistent

DT₅₀ (field)

174

Persistent

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

717

DT₅₀ modelling endpoint

Note

EU dossier lab studies DT₅₀ range 77-341 days, field studies DT₅₀ range 104-228 days

Dissipation rate RL₅₀ on plant matrix

Value

2.5

Note

Published literature RL₅₀ range 1.7-5.1 days, 6 field & undercover grown crops, various matrices, n=8

Dissipation rate RL₅₀ on and in plant matrix

Value

4.9

Note

Published literature RL₅₀ range 0.25-16.6 days, 23 field & undercover grown crops, various matrices, n=61

Aqueous photolysis DT₅₀ (days) at pH 7

Value

0.2

Fast

Note

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

Value

Stable

Note

Stable pH 5 to pH 7, DT₅₀ approx 1 year at pH 9, all at 25 °C

Water-sediment DT₅₀ (days)

129

Slow

Water phase only DT₅₀ (days)

Stable

Soil adsorption and mobility

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

2.23

Moderately mobile

K_foc

225

¹/_n

0.802

Notes and range

EU dossier K_f range 0.956-4.18, K_foc range 109-411 mL g⁻¹, ¹/_n range 0.744-0.888, Soils=12

pH sensitivity

Key metabolites

Metabolite

Formation medium

Estimated maximum occurrence fraction

1107/2009 relevancy

1-((6-chloro-3-pyridinyl)methyl)N-nitro-1H-imidazol-2-amine

Soil

0.018

Minor fraction, Relevant

6-chloronicotinic acid

Soil

Minor fraction, Relevancy unknown

Other known metabolites

Metabolite name and reference

Aliases

Formation medium / Rate

Estimated maximum occurrence fraction

Metabolising enzymes

1[(6-Chloro-3-pyridinyl)methyl]-4,5-dihydro-2-(nitroamino)-1H-imidazol-4-ol

imidaclopric metabolite M02

Animal

[(6-Chloro-3-pyridinyl)methyl]-4,5-dihydro-2-(nitroamino)-1H-imidazol-5-ol

imidaclopric metabolite M01

Rat; Water; Plant

1-[(6-chloro-3-pyridinyl)methyl]-, oxohydrazone

imidaclopric metabolite M07; NTN33893-nitrosimine

Plant; Animal

1-[(6-chloropyridin-3-yl)methyl]imidazolidin-2-one

imidaclopric metabolite M12; NTN33893-urea

Plant; Animal

1-[(6-chloropyridin-3-yl)methyl]imidazolidin-2-imine

imidaclopric metabolite M09; NTN33893-desnitro

Plant; Animal

6-chloropyridine-3-carboxylic acid

imidaclopric metabolite M14

Plant

ECOTOXICOLOGY

Property

Value

Source; quality score; and other information

Interpretation

Bio-concentration factor

BCF (l kg⁻¹)

0.61

Estimated

Low potential

CT₅₀ (days)

Not available

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

131

Mouse LD₅₀ (Rat) = 424 (F4)

Moderate

Mammals - Short term dietary NOEL

(mg kg⁻¹)

> 13

Rat

High

(ppm diet)

> 120

Birds - Acute LD₅₀ (mg kg⁻¹)

Coturnix japonica

High

Birds - Short term dietary (LC₅₀/LD₅₀)

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

> 83

Oncorhynchus mykiss

Moderate

Fish - Chronic 21 day NOEC (mg l⁻¹)

9.02

Oncorhynchus mykiss

Moderate

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

Daphnia magna

Moderate

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

1.8

Daphnia magna

Moderate

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

0.034

Americamysis bahia

High

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

0.055

Chironomus riparius

High

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

> 0.0021

Chironomus riparius

High

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

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

Non-target plants

> 100

Avena sativa Brassica rapa
Seedling emergence, ER₅₀
as mg kg⁻¹ soil

> 100

Avena sativa Brassica rapa
Vegetative vigour, ER₅₀
as mg kg⁻¹ soil

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

> 10

Scenedemus subspicatus

Low

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

Scenedesmus subspicatus

Low

Honeybees (Apis spp.)

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

0.081

Apis mellifera

High

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

0.0037

Apis mellifera

High

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)

0.218

Bombus terrestris 72hr

High

Literature DT₅₀ values range 0.014-0.554 µg bee⁻¹

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

0.038

Bombus terrestris 72hr

High

Literature DT₅₀ values range 0.006-0.23 µg bee⁻¹

Mason bees (Osmia spp.)

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

0.031

Osmia bicornis

High

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)

0.17

Megachile rotundata

High

Mode of exposure

Contact

Other pollinators (2)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

24.5

Scaptotrigona postica

Moderate

Mode of exposure

Oral

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

10.7

Eisenia foetida

Moderate

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

>= 0.178

Eisenia foetida

Moderate

Other soil macro-organisms

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Other arthropod (1)

LR₅₀ g ha⁻¹

0.022

Aphidius rhopalosiphi

% Effect

Other arthropod (2)

LR₅₀ g ha⁻¹

4.23

Typhlodromus pyri

% Effect

Soil micro-organisms

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

Dose: 2.25 kg ha⁻¹ 28 days

Mesocosm study data

NOEAEC mg l⁻¹

0.0006

Chironomids Batidae

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)

131

Mouse LD₅₀ (Rat) = 424 (F4)

Moderate

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

5000

Rat

Mammals - Inhalation LC₅₀ (mg l⁻¹)

> 0.069

Rat 4 hr (aerosol)

Other Mammal toxicity endpoints

Intraperitoneal LD₅₀ = 35 mg kg⁻¹

Mouse

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

0.06

Rat SF=100

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

0.08

Dog 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)

0.08

Dog SF=100

Dermal penetration studies (%)

0.3-8.0

concentration dependent

Dangerous Substances Directive 76/464

Exposure Routes

Public

Acceptable for proposed uses

Occupational

Acceptable for proposed uses
Occupational exposure may occur through dermal contact

European MRLs

EU MRL pesticide database

Drinking Water Standards

Drinking Water MAC (μg l⁻¹)

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

Moderately toxic
Potential liver, kidney, thyroid, heart and spleen toxicant

Handling issues

Property

Value and interpretation

General

Not explosive or oxidising
IMDG Transport Code is usually 9

CLP classification 2013

Health: H302
Environment: H400, H410

EC Risk Classification

Xn - Harmful: R22
N - Dangerous for the environment: R50, R53

EC Safety Classification

S2, S22, S57, S60, S61

WHO Classification

II (Moderately hazardous)

UN Number

Usually 3082

Waste disposal & packaging

Packaging Group III (minor danger)

TRANSLATIONS

Language

Name

English

imidacloprid

French

imidaclopride

German

Imidacloprid

Danish

imidacloprid

Italian

imidacloprid

Spanish

imidacloprid

Greek

Polish

imidachlopryd

Swedish

imidakloprid

Hungarian

imidaklorid

Dutch

imidacloprid

Record last updated:	05/07/2020
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