10290. Metaflumizone

Nomenclature

CAS number: 139968-49-3
2-[2-(4-Cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(trifluoromethoxy)phenyl]hydrazinecarboxamide; (EZ)-2′-[2-(4-cyanophenyl)-1-(α,α,α-trifluoro-m-tolyl)ethylidene]-4-(trifluoromethoxy)carbanilohydrazide; BAS-320I; Alverde (BASF); ProMeris (Fort Dodge); Siesta (BASF).
C24H16F6N4O2; mol wt 506.40.
C 56.92%, H 3.18%, F 22.51%, N 11.06%, O 6.32%.

Description and references

Semicarbazone insecticide dervied from pyrazoline that blocks voltage-dependent sodium channels. Prepn: K. Takagi et al., EP 462456; eidem, US 5543573 (1991, 1996 both to Nihon Nohyaku). Laboratory trial against Colorado potato beetle: G. C. Cutler et al., Resistant Pest Manag. Newsl. 16, 33 (2006). Field trial for control of red imported fire ants: X. P. Hu, D. Song, Sociobiology 50, 1107 (2007); against beet armyworm in tomato: J. E. Taylor, D. G. Riley, J. Entomol Sci. 42, 430 (2007). Series of articles on discovery, development, mode of action, efficacy, and pharmacokinetics for veterinary use: Vet. Parasitol. 150, 175-281 (2007) DOI. Toxicological profile: K. Hempel et al., ibid., 190 DOI PubMed. Efficacy of spot-on formulation against KS1 flea strain in cats: M. Dryden et al., ibid. 151, 74 (2008) DOI PubMed.

Chemical structure

Properties

Crystals from ether-n-hexane, mp 191°. Rapidly isomerizes to a mixture of 90% E-isomer and 10% Z-isomer. LD50 in rats (mg/kg): >5000, >5000 orally, dermally; LC50 (4 hr.) in rats: >5.2 mg/l by inhalation (Hempel).

Use

Insecticide.

Therapeutic Category (Veterinary)

Ectoparasiticide.