Imidacloprid

Imidacloprid

Names
IUPAC name N-{1-[(6-Chloro-3-pyridyl)methyl]-4,5-dihydroimidazol-2-yl}nitramide
Identifiers
CAS Number	138261-41-3 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:39169 Y
ChEMBL	ChEMBL406819 Y
ChemSpider	77934 Y
DrugBank	DB07980 Y
ECHA InfoCard	100.102.643
KEGG	C11110 Y
PubChem	86418
UNII	3BN7M937V8 Y
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) Y Key: YWTYJOPNNQFBPC-UHFFFAOYSA-N Y InChI=1/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) Key: YWTYJOPNNQFBPC-UHFFFAOYAZ
SMILES [O-][N+](=O)NC/1=N/CCN\1Cc2cnc(Cl)cc2
Properties
Chemical formula	C9H10ClN5O2
Molar mass	255.661
Appearance	Colorless crystals
Melting point	136.4 to 143.8 °C (277.5 to 290.8 °F; 409.5 to 416.9 K)
Solubility in water	0.51 g/L (20 °C)
Pharmacology
ATCvet code	QP53AX17 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (what is YN ?)
Infobox references

Imidacloprid is a systemic insecticide which acts as an insect neurotoxin and belongs to a class of chemicals called the neonicotinoids which act on the central nervous system of insects, with much lower toxicity to mammals. The chemical works by interfering with the transmission of stimuli in the insect nervous system. Specifically, it causes a blockage of the nicotinergic neuronal pathway. By blocking nicotinic acetylcholine receptors, imidacloprid prevents acetylcholine from transmitting impulses between nerves, resulting in the insect's paralysis and eventual death. It is effective on contact and via stomach action. Because imidacloprid binds much more strongly to insect neuron receptors than to mammal neuron receptors, this insecticide is more toxic to insects than to mammals.

As of 1999, Imidacloprid was the most widely used insecticide in the world. Although it is now off patent, the primary manufacturer of this chemical is Bayer CropScience (part of Bayer AG). It is sold under many names for many uses; it can be applied by soil injection, tree injection, application to the skin of the plant, broadcast foliar, ground application as a granular or liquid formulation, or as a pesticide-coated seed treatment. Imidacloprid is widely used for pest control in agriculture. Other uses include application to foundations to prevent termite damage, pest control for gardens and turf, treatment of domestic pets to control fleas, protection of trees from boring insects, and in preservative treatment of some types of lumber products .

Recent research suggests that widespread agricultural use of imidacloprid and other pesticides may be contributing to honey bee colony collapse disorder, the decline of honey bee colonies in Europe and North America observed since 2006. As a result, several countries have restricted use of imidacloprid and other neonicotinoids. In January 2013, the European Food Safety Authority stated that neonicotinoids pose an unacceptably high risk to bees, and that the industry-sponsored science upon which regulatory agencies' claims of safety have relied, may be flawed, or even deceptive.