Thiamethoxam

Thiamethoxam
IUPAC name 3-[(2-Chloro-1,3-thiazol-5-yl)methyl]-5-methyl-N-nitro-1,3,5-oxadiazinan-4-imine
Identifiers
CAS number	153719-23-4 Y
PubChem	5485188
ChemSpider	4588645 Y
UNII	747IC8B487 Y
KEGG	C18513 Y
Jmol-3D images	Image 1
SMILES Clc1ncc(s1)CN2/C(=N\[N+]([O-])=O)N(C)COC2
InChI InChI=1S/C8H10ClN5O3S/c1-12-4-17-5-13(8(12)11-14(15)16)3-6-2-10-7(9)18-6/h2H,3-5H2,1H3/b11-8- Y Key: NWWZPOKUUAIXIW-FLIBITNWSA-N Y InChI=InChI=1S/C8H10ClN5O3S/c1-12-4-17-5-13(8(12)11-14(15)16)3-6-2-10-7(9)18-6/h2H,3-5H2,1H3/b11-8-
Properties
Molecular formula	C8H10ClN5O3S
Molar mass	291.71 g mol−1
Density	1.57 g/cm3
Melting point	139.1 °C, 412 K, 282 °F
Solubility in water	4.1 g/L
Hazards
R-phrases	R22
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Thiamethoxam is an insecticide in the class of neonicotinoids. It has a broad spectrum of activity against many types of insects.

History

Thiamethoxam was developed by Syngenta but a patent dispute arose with Bayer which already had patents covering other neonicotinoids including imidacloprid. In 2002 the dispute was settled, with Syngenta paying Bayer $120 million in exchange for worldwide rights to thiamethoxam.

Uses

Thiamethoxam is a systemic insecticide that is absorbed quickly by plants and transported to all parts of the plant, where it acts as a deterrent to insect feeding. It is active in the stomach of the insects, and also through direct contact. The compound blocks the electron transfer between nerve cells, making the insects become paralyzed.

Thiamethoxam is effective against aphids, thrips, beetles, centipedes, millipedes, sawflies, leaf miners, stem borers and termites.

Thiamethoxam is a moderately toxic substance. In normal use, there are no unacceptable risks involved. The substance is toxic to bees and harmful to aquatic and soil organisms. A metabolite of thiamethoxam in soil is clothianidin.