Monofluoroacetate

Health and Safety Factors. Completely fluorinated alkanes are essentially nontoxic (16). Rats exposed for four hours to 80% perfluorocyclobutane and 20% oxygen showed only slight effects on respiration, but no pathological changes in organs. However, some fluorochemicals, especially functionalized derivatives and fluoroolefins, can be lethal. Monofluoroacetic acid and perfluoroisobutylene [382-21-8] are notoriously toxic (16). 

Hydrofluorocarbons generally are less toxic than HGFGs, with the notable exception of HFG-152, GH2FGH2F, which apparently can be metabohcaHy converted to monofluoroacetic acid and is therefore quite toxic (44). 

A synthetically valuable reaction sequence is the chlorodifluoroacetylation of various substituted allylic alcohols and the subsequent Reformatskii-Claisen rearrangement of the ester thus formed to interesting 2,2-difluoropentenoic acid derivatives [25] (equation H) Comparable sequences have been reported for ally monofluoroacetates [26] and allyl 3,3,3-trifiuoropropanoates [27] (equations 15 and 16). 

A further way in which metabolic control may be exercised is the artificial deprivation of required ions and cofactors, for example aconitase must have ferrous ions for activity. Conversely, addition of toxic ions is possible, for example aconitase is inhibited by cupric ions. Finally the use of metabolic analogues is possible. If monofluoroacetate is added to cells then monofluorocitrate is produced by titrate synthase and this compound inhibits the activity of aconitase. Great care has to be taken when using metabolic analogues, however, they are often less than 100% specific and may have unexpected and unwanted serious side effects. 

Aulerich RJ, Ringer RK, Safronoff J. 1987. Primary and secondary toxicity of warfarin, sodium monofluoroacetate, and methyl parathion in mink. Arch Environ Contam Toxicol 16 357-366. 

Monofluoroacetic acid offers little promise as a mosquito larvicide, but 2-ethylhexyl monofluoroacetate is a very powerful aphicide. The high toxicity of the fluorinated lower aliphatic acids and their esters to vertebrates probably precludes their use as insecticides except under highly controlled conditions. The toxicity of the fluorinated acids to the vertebrates is attributed to their interference with an enzyme system, but the possibility of finding one with a high specificity for insects is not excluded. 

Batcheler, C.L. and C.N. Challies. 1988. Loss of compound 1080 (sodium monofluoroacetate) from carbopol gel smeared on foliage to poison deer. N.Z. Jour. Forest. Sci. 18 109-115. 

Chenoweth, M.B. 1949. Monofluoroacetic acid and related compounds. Pharmacol. Rev. 1 383424. 

Eason, C.T. and C.M. Frampton. 1991. Acute toxicity of sodium monofluoroacetate (1080) baits to feral cats. Austral. Wildl. Res. 18 445-449. 

Eason, C.T., C.M. Frampton, R. Henderson, M.D. Thomas, and D.R. Morgan. 1993a. Sodium monofluoroacetate and alternative toxins for possum control. N.Z. Jour. Zool. 20 329-334. 

Eason, C.T., R. Gooneratne, H. Fitzgerald, G. Wright, and C. Frampton. 1994. Persistence of sodium monofluoroacetate in livestock animals and risk to humans. Human Exper. Toxicol. 13 119-122. 

Eason, C.T., G.R. Wright, and H. Fitzgerald. 1992. Sodium monofluoroacetate (1080) water-residue analysis after large-scale possum control. N.Z. Jour. Ecol. 16 47 4-9. 

Eastland, W.G. and S.L. Beasom. 1987. Acute toxicity of sodium monofluoroacetate to the striped skunk. Bull. Environ. Contam. Toxicol. 38 934-936. 

Eisler, R. 1995. Sodium Monofluoroacetate (1080) Hazards to Fish, Wildlife, and Invertebrates A Synoptic Review. U.S. Natl. Biol. Serv., Biol. Rep. 27. 47 pp. 

Hoogenboom, J.J.L. and C.G. Rammell. 1987. Determination of sodium monofluoroacetate (compound 1080) in tissues and baits as its benzyl ester by reaction-capillary gas chromatography. Jour. Anal. Toxicol. 11 140-143. 

Homshaw, T.C., R.K. Ringer, R.J. Aulerich, and H.H. Casper. 1986. Toxicity of sodium monofluoroacetate (compound 1080) to mink and European ferrets. Environ. Toxicol. Chem. 5 213-223. 

Hugghins, E.J., H.H. Casper, and C.D. Ward. 1988. Tissue fluoroacetate residues in prairie dogs dosed with low-level sodium monofluoroacetate. Jour. Assoc. Offic. Anal. Chem. 71 579-581. 

Kimball, B.A. and E.A. Mishalanie.1993. Gas chromatographic determination of sodium monofluoroacetate as the free acid in an aqueous solvent. Jour. Chmmatogr. 634 289-296. 

King, D.R., L.E. Twigg, and J.L. Gardner. 1989. Tolerance to sodium monofluoroacetate in dasyurids from Western Australia. Austral. Wildl. Res. 16 131-140. 

Kun, E. 1982. Monofluoroacetic acid (compound 1080), its pharmacology and toxicology. Pages 34-41 in R.E. Marsh (ed.). Proceedings Tenth Vertebrate Pest Conference. Univ. California, Davis, CA. 

Lynch, G.W. and R.D. Nass. 1981. Sodium monofluoroacetate (1080) relation of its use to predation on livestock in western national forests. Jour. Range Manage. 34 421-423. 

O Brien, P.H. 1988. The toxicity of sodium monofluoroacetate (compound 1080) to captive feral pigs, Sus scrofa. Austral. Wildl. Res. 15 163-170. 

Ozawa, H. and T. Tsukioka. 1987. Gas chromatographic determination of sodium monofluoroacetate in water by derivatization with dicyclohexylcarbodiimide. Anal. Chem. 59 2914-2917. 

Peacock, E.A. 1964. Sodium Monofluoroacetate (Compound 1080). U.S. Bur. Sport Fish. Wildl., Div. Predator Rodent Cont., Circ. Letter dated 1 July 1964. Mimeogr. 26 pp. 

Robison, W.H. 1970. Acute toxicity of sodium monofluoroacetate to cattle. Jour. Wildl. Manage. 34 647-648. 

Savarie, P.J., G.H. Matschke, R.M. Engeman, and K.A. Fagerstone. 1994. Susceptibility of prairie dogs to compound 1080 (sodium monofluoroacetate) baits and secondary poisoning effects in European ferrets under laboratory conditions. Pages 134-143 in A.A. Seawright and C.T. Eason (eds.). Proceedings of the Science Workshop on 1080. Roy. Soc. N.Z., Misc. Ser. 28. 

---