8271. Rotenone

Nomenclature

CAS number: 83-79-4
[2R-(2α,6aα,12aα)]-1,2,12,12a-Tetrahydro-8,9-dimethoxy-2-(1-methylethenyl)-[1]benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6(6aH)-one; Canex (Mallinckrodt Vet.); Noxfire (AgrEvo).
C23H22O6; mol wt 394.42.
C 70.04%, H 5.62%, O 24.34%.

Description and references

Principal insecticidal constituent of derris root, cubé, etc. Powerful inhibitor of mitochondrial electron transport. Isoln from Lonchocarpus nicou (Aubl.) DC., Leguminosae: Geoffrey, Ann. Inst. Colon. Marseille 2, 1 (1895). Review of structure: La Forge et al., Chem. Rev. 12, 181 (1933); Butenandt, McCartney, Ann. 494, 17 (1932); King, Annu. Rep. Prog. Chem. 29, 186 (1932). Absolute configuration: Büchi et al., J. Chem. Soc. 1961, 2843; Nakazaki, Arakawa, Bull. Chem. Soc. Jpn. 34, 1246 (1961); Begley et al., Chem. Commun. 1975, 850. NMR spectrum: Crombie, Lown, ibid. 1962, 775. Total synthesis: Miyano et al., Agric. Biol. Chem. 25, 673 (1961); Miyano, J. Am. Chem. Soc. 87, 3958 (1965). Alternate synthesis: Crombie et al., J. Chem. Soc. Perkin Trans. 1 1973, 1277, eidem, Chem. Commun. 1979, 1142; I. Sasaki, K. Yamashita, Agric. Biol. Chem. 43, 137 (1979). Synthesis of stereoisomers: Unai, Yamamoto, ibid. 37, 897 (1973). Toxicology: Santi, Toth, Farmaco Ed. Sci. 20, 270 (1965). Toxicity data: J.-I. Fukami et al., Science 155, 713 (1967). Review: H. Fukami, M. Nakajima in Naturally Occurring Insecticides, M. Jacobson, D. G. Crosby, Eds. (Dekker, New York, 1971) pp 71-97; S. B. Soloway, Environ. Health Perspect. 14, 109-117 (1976); T. J. Haley, J. Environ. Pathol. Toxicol. 1, 315-337 (1978).

Chemical structure

Properties

Orthorhombic, six-sided plates from trichloroethylene, mp 165-166° (dimorphic form, mp 185-186°). [α]D20 -228° (c = 2.22 in benzene). uv spectra: Büchi et al., loc. cit. Practically insol in water. Sol in alcohol, acetone, carbon tetrachloride, chloroform, ether, and many other organic solvents. Dec upon exposure to light and air. Colorless solns in organic solvents oxidize upon exposure and become yellow, orange and then deep red and may deposit crystals of dehydrorotenone and rotenonone which are toxic to insects. LD50 i.p. in mice: 2.8 mg/kg (Fukami); in rats (mg/kg): 132 orally; 6 i.v. (Soloway).

Caution

Potential symptoms of overexposure are irritation of eyes, skin, respiratory system; numbness of mucous membranes; nausea, vomiting, abdominal pain; muscle tremors, incontinence, clonic convulsions, stupor. See NIOSH Pocket Guide to Chemical Hazards (DHHS/NIOSH 97-140, 1997) p 274. Inhalation may cause severe pulmonary irritation. See Clinical Toxicology of Commercial Products, R. E. Gosselin et al., Eds. (Williams & Wilkins, Baltimore, 5th ed., 1984) Section III, pp 366-368.

Use

Pesticide.

Therapeutic Category (Veterinary)

Ectoparasiticide.