Chemical Properties
Pale Yellow Solid
Definition
ChEBI: The (E)-stereoisomer of acetamiprid.
Agricultural Uses
Insecticide: This class of pesticides are chemically related to nicotine and used on corn and soybean seeds and are used to control sucking and chewing insects, and soil insects including
aphids, beetles, fruit moth, leaf-hoppers and-miners, thrips,
whiteflies [83] . Also used to control fleas on domestic animals.
Synthesis
In a 250 mL reaction flask, N-cyano-N'-(2-chloro-5-pyridinylmethyl)acetamidine 20.5 g (85.27%), chloroform 54.5 mL, and methylbutylammonium bromide 0.11 g. With stirring, cooled to 15 ° C. At the same time, dropwise addition of 11.6 g of dimethyl sulf
Metabolic pathway
Acetamiprid is relatively stable to hydrolysis and to photodegradation
by sunlight. It is rapidly degraded in soils to form 6-chloropyridinyldimethylamine
and 6-chloronicotinic acid. The main pathways
of metabolism in plants are N-demethylation and subsequent oxidation
affording 6-chloronicotinic acid and 6-chloropicolyl alcohol. Two N-cyanoamidines
were formed after application of acetamiprid to cabbage
leaves. No information is available on the fate of the insecticide in insects
or mammals.
Degradation
Acetamiprid is stable in buffer solutions at pH 4, 5 and 7 and under
sunlight. It is degraded slowly at pH 9 (45 °C) (PM). In a study of its
hydrolysis acetamiprid was converted quantitatively to N-methyl-
(6-chloro-3-pyridyl)methylamine (2) in 0.5-1 N sodium hydroxide at
90-95°C in 2 hours (see Scheme 1). N-Demethyl-acetamiprid (3) was
converted to (6-chloro-3-pyridyl)methylamine(4) at the same rate and
under similar conditions (Tokieda et al., 1997).
