Clothianidin
Title: Clothianidin
CAS Registry Number: 210880-92-5
CAS Name: [C(E)]-N-[(2-Chloro-5-thiazolyl)methyl]-N¢-methyl-N¢¢-nitroguanidine
Additional Names: (E)-1-(2-chloro-1,3-thiazol-5-ylmethyl)-3-methyl-2-nitroguanidine
Manufacturers' Codes: TI-435
Trademarks: Arena (Arvesta); Poncho (Bayer CropSci.)
Molecular Formula: C6H8ClN5O2S
Molecular Weight: 249.68
Percent Composition: C 28.86%, H 3.23%, Cl 14.20%, N 28.05%, O 12.82%, S 12.84%
Literature References: Neonicotinoid insecticide for use in food crops. Prepn: H. Uneme et al., EP 376279; eidem, US 5034404 (1990, 1991 both to Takeda); eidem, Pestic. Sci. 55, 202 (1999). Synthesis: P. Maienfisch et al., Tetrahedron Lett. 41, 7187 (2000). Insecticidal activity and physical properties: Y. Ohkawara et al., Brighton Crop Prot. Conf. - Pests Dis. 1, 51 (2002). Field trials in sugar beets: R. H. Meredith et al., ibid. 2, 691 (2002); and cereals: A. M. Dewar et al., ibid. 647. Ecotoxicological profile: R. Schmuck, J. Keppler, Pflanzenschutz-Nachr. Bayer 56, 26 (2003). Metabolism studies: O. Klein, ibid. 75. Review of use in corn: W. Andersch, M. Schwarz, ibid. 147-172.
Properties: White crystalline powder, mp 176.8°. Vapor pressure (Pa): 1.3 ´ 10-10 (25°); 3.8 ´ 10-7 (20°). Soly (g/l) at 20°: water 0.327; at 25°: acetone 15.2, methanol 6.26, ethyl acetate 2.03, xylene 0.013. Log P (n-octanol/water) at 25°: 0.7. LD50 in rats (mg/kg): >5000 orally; >2000 dermally. LC50 in rats (mg/l): >6.1 inhalation. LC50 in bobwhite quail, mallard duck (ppm): >5200, >5200 (dietary). LC50 (96 hr) in rainbow trout, bluegill (mg/l): >100, >120 (Ohkawara).
Melting point: mp 176.8°
Log P: Log P (n-octanol/water) at 25°: 0.7
Toxicity data: LD50 in rats (mg/kg): >5000 orally; >2000 dermally; LC50 in rats (mg/l): >6.1 inhalation; LC50 in bobwhite quail, mallard duck (ppm): >5200, >5200 (dietary); LC50 (96 hr) in rainbow trout, bluegill (mg/l): >100, >120 (Ohkawara)
Use: Insecticide.

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