imidacloprid (Ref: BAY NTN 33893) ** Translations

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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
for imidacloprid

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

EC Regulation 1107/2009 (repealing 91/414):

Status	Approved
Dossier rapporteur/co-rapporteur	Germany/Netherlands
Date inclusion expires	31/07/2022
EU Candidate for substitution (CfS)	No
Listed in EU database	Yes

Approved for use () or known to be used () in the following European countries:

AT

BE

BG

CY

CZ

DE

DK

EE

EL

ES

FI

FR

HR

HU

IE

IT

LT

LU

LV

MT

NL

PL

PT

RO

SE

SI

SK

UK

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

General status:

Pesticide type	Insecticide, Veterinary substance
Substance group	Neonicotinoid
Minimum active substance purity	970 g/kg
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 (g mol-1)	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)	4A
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	Bayer CropScience Makhteshim-Agan Scotts
Example products using this active	Admire Chinook Blue Tripod Plus Gaucho Raxil
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
for imidacloprid

Property		Value	Source/Quality Score/Other Information	Interpretation
Solubility - In water at 20oC (mg l-1)		610	A5	High
Solubility - In organic solvents at 20oC (mg l-1)		67000	A5 - Dichloromethane	-
		690	A5 - Toluene	-
		100	A5 - n-Hexane	-
		2300	A5 - 2-Propanol	-
Melting point (oC)		144	A5	-
Boiling point (oC)		Decomposes before boiling	A3	-
Degradation point (oC)		230	A5	-
Flashpoint (oC)		Not expected to self ignite; Not highly flammable	A5	-
Octanol-water partition coefficient at pH 7, 20oC	P	3.72 X 1000	Calculated	-
	Log P	0.57	A5	Low
Bulk density (g ml-1)/Specific gravity		1.54	A5	-
Dissociation constant (pKa) at 25oC		Not applicable	A5	-
		Note: No dissociation
Vapour pressure at 20oC (mPa)		4.0 X 10-07	A5	Low volatility
Henry's law constant at 25oC (Pa m3 mol-1)		1.7 X 10-10	A5	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		-	Calculated	Medium
Maximum UV-vis absorption L mol-1 cm-1		212nm = 13346, 270nm = 22054	A5	-
Surface tension (mN m-1)		72.2	A5 at 20oC	-

Degradation:

Property		Value	Source/Quality Score/Other Information	Interpretation
General biodegradability		-
Soil degradation (days) (aerobic)	DT50 (typical)	191	B5	Persistent
	DT50 (lab at 20oC)	187	A5	Persistent
	DT50 (field)	174	A5	Persistent
	DT90 (lab at 20oC)	-	-	-
	DT90 (field)	717	A5	-
	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	R4	-
	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	R4	-
	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	A5	Fast
	Note	-
Aqueous hydrolysis DT50 (days) at 20oC and pH 7	Value	Stable	A5	-
	Note	Stable pH 5 to pH 7, DT50 approx 1 year at pH 9, all at 25 deg C
Water-sediment DT50 (days)		129	A5	Slow
Water phase only DT50 (days)		30	A5	Stable

Soil adsorption and mobility:

Property		Value	Source/Quality Score/Other Information	Interpretation
Linear	Kd	-	-	-
	Koc	-
	Notes and range	-
Freundlich	Kf	2.23	A5	Moderately mobile
	Kfoc	225
	1/n	0.802
	Notes and range	EU dossier Kf range 0.956-4.18, Kfoc range 109-411 mL/g, 1/n range 0.744-0.888, Soils=12
pH sensitivity		No

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
for imidacloprid

Property		Value	Source/Quality Score/Other Information	Interpretation
Bio-concentration factor	BCF (l kg-1)	0.61	Q2 Estimated	Low potential
	CT50 (days)	Not available		-
Mammals - Acute oral LD50 (mg kg-1)		131	A5 Mouse, LD50 (Rat) = 424 (F4)	Moderate
Mammals - Short term dietary NOEL	(mg kg-1)	> 13	B5 Rat	High
	(ppm diet)	> 120		-
Birds - Acute LD50 (mg kg-1)		31	A5 Coturnix japonica	High
Birds - Short term dietary (LC50/LD50)		-	-	-
Fish - Acute 96 hour LC50 (mg l-1)		> 83	A5 Oncorhynchus mykiss	Moderate
Fish - Chronic 21 day NOEC (mg l-1)		9.02	A5 Oncorhynchus mykiss	Moderate
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1)		85	A5 Daphnia magna	Moderate
Aquatic invertebrates - Chronic 21 day NOEC (mg l-1)		1.8	A5 Daphnia magna	Moderate
Aquatic crustaceans - Acute 96 hour LC50 (mg l-1)		0.034	A5 Americamysis bahia	High
Sediment dwelling organisms - Acute 96 hour LC50 (mg l-1)		0.055	A5 Chironomus riparius	High
Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l-1)		> 0.0021	A5 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	A5 Avena sativa, Brassica rapa Seedling emergence, ER50 as mg/kg soil	-
		> 100	A5 Avena sativa, Brassica rapa Vegetative vigour, ER50 as mg/kg soil	-
Algae - Acute 72 hour EC50, growth (mg l-1)		> 10	A5 Scenedemus subspicatus	Low
Algae - Chronic 96 hour NOEC, growth (mg l-1)		10	A5 Scenedesmus subspicatus	Low
Honeybees (Apis spp.)	Contact acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1)	0.081	A5 Apis mellifera	High
	Oral acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1)	0.0037	A5 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	A5 Bombus terrestris, 72hr	High
		Literature DT50 values range 0.014-0.554 ug/bee
	Oral acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1)	0.038	A5 Bombus terrestris, 72hr	High
		Literature DT50 values range 0.006-0.23 ug/bee
Mason bees (Osmia spp.)	Contact acute LD50 (worst case from 24 , 48 and 72 hour values - μg bee-1)	0.031	R4 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	R4 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	R4 Scaptotrigona postica	Moderate
	Mode of exposure	Oral
Earthworms - Acute 14 day LC50 (mg kg-1)		10.7	A5 Eisenia foetida	Moderate
Earthworms - Chronic NOEC, reproduction (mg kg-1)		>= 0.178	A5 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	A5 Aphidius rhopalosiphi	-
	% Effect	-	-	-
Other arthropod (2)	LR50 g ha-1	4.23	A5 Typhlodromus pyri	-
	% Effect	-	-	-
Soil micro-organisms		Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect	A5 Dose: 2.25 kg ha-1, 28 days	-
Mesocosm study data	NOEAEC mg l-1	0.0006	A5 Chironomids, Batidae	-
	NOEAEC mg l-1	-	-	-

HUMAN HEALTH AND PROTECTION
for imidacloprid

General:

Property		Value	Source/Quality Score/Other Information	Interpretation
Threshold of Toxicological Concern (Cramer Class)		High (class III)	-	-
Mammals - Acute oral LD50 (mg kg-1)		131	A5 Mouse, LD50 (Rat) = 424 (F4)	Moderate
Mammals - Dermal LD50 (mg kg-1 body weight)		> 5000	A5 Rat	-
Mammals - Inhalation LC50 (mg l-1)		> 0.069	A5 Rat, 4 hr (aerosol)	-
Other Mammal toxicity endpoints		Intraperitoneal LD50 = 35 mg kg-1	V3 Mouse	-
ADI - Acceptable Daily Intake (mg kg-1bw day-1)		0.06	A5 Rat, SF=100	-
ARfD - Acute Reference Dose (mg kg-1bw day-1)		0.08	A5 Dog, SF=100	-
AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1)		-	-	-
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1)		0.08	A5 Dog, SF=100	-
Dermal penetration studies (%)		0.3-8.0	A5, 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		Click here for the EU MRL pesticide database
Drinking Water Standards		-	-	-
Drinking Water MAC (μg l-1)		-	-	-

Health issues:

Carcinogen	Genotoxic	Endocrine disrupter	Reproduction / development effects	Cholinesterase inhibitor	Neurotoxicant
	A3; B3; C3; D3; E2	-
Respiratory tract irritant	Skin irritant	Skin sensitiser	Eye irritant	Phototoxicant
		-		-
General human health issues		Moderately toxic Potential liver, kidney, thyroid, heart and spleen toxicant
Key: Genotoxicity A: Chromosome aberration (EFSA database) B: DNA damage/repair (EFSA database) C: Gene mutation (EFSA database) D: Genome mutation (EFSA database) E: Unspecified genotoxicity type (miscellaneous data source) 0: No data 1: Positive 2: Mixed/ambiguous results 3: Negative			Key: Other : Yes, known to cause a problem : No, known not to cause a problem : Possibly, status not identified - : No data found

Handling issues:

Property		Value	Source/Quality Score/Other Information	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
for imidacloprid

Language	Name
English	imidacloprid
French	imidaclopride
German	Imidacloprid
Danish	imidacloprid
Italian	imidacloprid
Spanish	imidacloprid
Greek	-
Slovenian	imidakloprid
Polish	imidachlopryd
Swedish	imidakloprid
Hungarian	imidaklorid
Dutch	imidacloprid

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Record last updated: Tuesday 25 June 2019
Contact: aeru@herts.ac.uk
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