63 



slowly by third instar tobacco budworms, Heliothi s vlrescens {J.). Oxidation 

 at th'J sulfur atom was the predominant reaction in both species of insects, 

 yielding primarily the sulfoxide derivative of Teraik and to a lesser extent the 

 sulfone. Traces of N-demethyl derivatives in excreta of the tobacco budworra 

 indicated some oxidation at the N-methyl position. The principal products of 

 hydrolysis were the sulfoxide and sulfone derivatives of 2-methyl-2-(methylthio) 

 proprionaldehyde oxime. 



110. ; Lindquist, D. A.; and Grabbe, R. R. 1967. Comparative fate of the 

 geometric isomers of phosphamidon in plants and animals. J. Econ. 

 Entomol. 60: 341-352. 



The fates of the cis and trans isomers of phosphamidon in plants and animals 

 were determined by using radiometric and other procedures. The biological 

 half-lives of toxic forms of the 2 isomers were very short in plants and 

 animals and of comparable duration. Although both isomers were converted 

 to similar oxidative and hydrolytic metabolites, the rates of formation were 

 somewhat different; the faster rate of oxidative N-dealkylation of cis 

 phosphamidon in all biological systems was particularly apparent. Not only 

 were the trans isomers of phosphamidon and its N-deethyl derivative sub- 

 stantially more toxic to adult boll weevils Anthonomus grand is Eoheman, and 

 house flies, Musca domestica L., than were the cis isomers, but they also 

 were significantly more potent inhibitors of acetylcholinesterase in the 

 insects. Combinations of sesamex with cis and trans phosphamidon and N- 

 deethyl derivatives caused a substantial increase in the toxicity of all 

 compounds to boll weevils, particularly the cis isomers. 



111. ; Stokes, R. A.; Hardee, D. D.; and Gueldner, R. C. 1971. Gas 

 chromatographic determination of the components of the synthetic 



boll weevil sex pheromone (grandlure) . J. Agric. Food Chem. 19: 202-203. 



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