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Acetamiprid is an alpha-Chloro-N-heteroaromatic compound. It is a neonicotinoid with a chloropyridinyl group and it is comparable to other neonicotinoids such as imidacloprid, nitenpyram and thiacloprid. These substances all have a 6-chloro-3-pyridine methyl group but differ in the nitroguanidine, nitromethylene, or cyanoamidine substituent on an acyclic or cyclic moiety.
There are two isomeric forms in acetamiprid with E and Z-configurations of the cyanoimino group. There are also a variety of stable conformers due to the rotation of single bonds in the N-pyridylmethylamino group. The E-conformer is more stable than the Z-conformer and assumed to be the active form. In solution, two different E-conformers exist which slowly change into each other.
Acetamiprid is used to produce a variety of crops, plants and flowers. It can be used combined with another pesticide with a different mode of action. This way the developing of resistance by pest species can be prevented. According to the US EPA acetamiprid could play a role in battling resistance in the species: Bemisia, greenhouse whiteflies and western flower thrips.
Neonicotinoids act as agonists for nAChR and are selectively toxic to insects versus mammals, because of a higher potency on insect than mammalian nAChRs. This increases their suitability as pesticides.
Acetamiprid Usage And Synthesis |
Definition | ChEBI: A carboxamidine that is acetamidine in which the amino hydrogens are substituted by a (6-chloropyridin-3-yl)methyl and a methyl group while the hydrogen attached to the imino nitrogen is replaced by a cyano group. |
Uses | Insecticide. |