9294. Thiamethoxam

Nomenclature

CAS number: 153719-23-4
3-[(2-Chloro-5-thiazolyl)methyl]tetrahydro-5-methyl-N-nitro-4H-1,3,5-oxadiazin-4-imine; CGA-293343; Actara (Syngenta); Adage (Syngenta); Cruiser (Syngenta).
C8H10ClN5O3S; mol wt 291.71.
C 32.94%, H 3.46%, Cl 12.15%, N 24.01%, O 16.45%, S 10.99%.

Description and references

Broad-spectrum chloronicotinyl insecticide. Prepn: P. Maienfisch, L. Gsell, CA 2100924 (1994 to Ciba-Geigy); eidem, US 5852012 (1998 to Novartis); T. G"obel et al., Pestic. Sci. 55, 343 (1999). Effect on feeding behavior of aphids: P. Harrewijn et al., Brighton Crop Prot. Conf. - Pests Dis. 1998, 813. LC-MS determn in fruits and vegetables: D. Zywitz et al., Dtsch. Lebensm. Rundsch. 99, 188 (2003). Review of physical properties and field trials: R. Senn et al., ibid. 27-36; of biological activity, metabolism, and physical properties: D. S. Lawson et al., Proc. Beltwide Cotton Conf. 2, 1106-1109 (1999).

Chemical structure

Properties

Crystalline powder, mp 139.1°. Soly in water at 25°: 4100 mg/l. Vapor pressure at 25°: 6.6 × 10-9 Pa. Log P (octanol/water) at 25°: -0.13. LD50 in rats (mg/kg): 1563 orally, >2000 dermally; LD50 in bobwhite quail, mallard duck (mg/kg): 1552, 576 orally. LC50 (96hr) in rainbow trout, bluegill (mg/l): >100, >114 (Senn).

Use

Insecticide.