Acetamipride

Acetamiprid, a member of the family. are a class of neuro- active chemically similar to . They target the nervous system of causing paralyzation. It is systemic and intended to control sucking insects on crops such as leafy vegetables, citrus fruits, pome fruits, grapes, , cole crops, and ornamental plants. It is also a key pesticide in commercial cherryfarming due to its effectiveness against the larvae of the cherry fruit fly. such as aphids and whiteflies without having detrimental effects on non-targets. It has also become common in household to combat bed bugs[1,5].

Neonicotinoids, like nicotine, bind to nicotinic acetylcholine receptors of a cell and trigger a response by that cell. In mammals, nicotinic acetylcholine receptors are located in cells of both the central and peripheral nervous systems. In insects these receptors are limited to the central- nervous-system[2].

While low to moderate activation of these receptors causes nervous stimulation, high levels overstimulate and block the receptors, causing paralysis and death. Nicotinic acetylcholine receptors are activated by the neurotransmitter acetylcholine.

Because most neonicotinoids bind much more strongly to neuronreceptors than to mammal neuron receptors, these insecticides are selectively more toxic to insects than mammals

Neonicotinoids are effective through several different modes of application, including foliarly and as a seed or soil treatment They have low hydrophobicity, which is related to their excellent systemic and translaminar activity[3]..

Acetamiprid pesticide has been classified as an “unlikely” human . In mammals, acetamiprid caused generalized, nonspecific toxicity and did not appear to have specific target organ toxicity[4,5]. Acetamiprid - Quick Reference

Name[2]: (E)-N1-[(6-Chlor-3-pyridyl)methyl]-N2-cyano- N1- methylacetamidin

Molecular formula: C10H11ClN4

CAS[2]: 135410-20-7

Molar Mass[2]: 222,68 g/mol

Characteristics[2]: colourless, stable, solid

Meltingpoint: 98,9°C

Solubility[4]: 4,25 g/L in Water

Synthesis:

Sodium hydride is added to a solution of N-cyano-N-methylacetamidine in N,N-dimethylformamide at 0°C. After stirring it for 1 hour at the same temperature 2-chloro-5-pyridylmethylchloride is added to the mixture followed by stirring 5 hours at room temperature. The reaction mixture is then poured into ice-water, extracted with ethylacetate, dried, and concentrated under reduced pressure. The residue obtained is purified by coloum chromatography on silica gel.

Source

[1] Ambrose, Margery , Characterization of the insecticidal properties of acetamiprid under field and laboratory conditions.( Dr. J.R. Bradley, Jr. and Dr. J.

[2] Pesticide Fact Sheet: EPA United States Environmental Protection Agency, March 15, 2002

[3] Peter Jeschke, Ralf Nauen, Michael Schindler, Alfred Elbert: Overview of the Status and Global Strategy for Neonicotinoids. In: Journals of Agricultural and Food Chemistry. Bd. 59, 2011, S. 2897–2908

[4 ]Dave Goulson: An overview of the environmental risks posed by neonicotinoid insecticides. In: Journal of Applied Ecology. 50, 2013, S. 977–987 [5] Peter Jeschke, Ralf Nauen, Michael Schindler, Alfred Elbert: Overview of the Status and Global Strategy for Neonicotinoids. In: Journals of Agricultural and Food Chemistry. Bd. 59, 2011, S. 2897–2908