10398. Flubendiamide

Nomenclature

CAS number: 272451-65-7
N2-[1,1-Dimethyl-2-(methylsulfonyl)ethyl]-3-iodo-N1-[2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-1,2-benzenedicarboxamide; 3-iodo-N1-(2-mesyl-1,1-dimethylethyl)-N-[4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-o-tolyl]phthalamide; NNI-0001; Belt (Bayer CropSci.); Fame (Bayer CropSci.); Fenos (Bayer CropSci.); Synapse (Bayer CropSci.).
C23H22F7IN2O4S; mol wt 682.39.
C 40.48%, H 3.25%, F 19.49%, I 18.60%, N 4.11%, O 9.38%, S 4.70%.

Description and references

Phthalic acid diamide pesticide; insect-specific ryanodine receptor activator. Prepn: M. Tohnishi et al., EP 1006107; eidem, US 6603044 (2000, 2003 both to Nihon Nohyaku); eidem, J. Pestic. Sci. 30, 354 (2005) DOI. Mechanism of action: T. Masaki et al., Mol. Pharmacol. 69, 1733 (2006) DOI PubMed. HPLC determn in rice: M. Gopal, E. Mishra, Bull. Environ. Contam. Toxicol. 81, 360 (2008) DOI PubMed. Comprehensive description: T. Nishimatsu et al., BCPC Int. Conf. - Crop Sci. Technol. 2005, 57-64. Review of field trials: D. Ebbinghaus et al., Pflanzenschutz-Nachr. Bayer (Engl. Ed.) 60, 219-246 (2007).

Chemical structure

Properties

White crystalline powder, mp 218-221°. Log P (octanol/water): 4.20 (25°). Vapor pressure (25°): <104 Pa. Soly in water (20°): 29.9 μg/l. LD50 in rats (mg/kg): >2000 orally; >2000 dermally. LC50 (96 hr) in carp: >548 μg/l (Nishimatsu).

Use

Insecticide.