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This publication is dedicated in the memory of Dr. Julie Fisher. 27). One of the more potent compounds (6) has been added to three different sixmers of DNA, in order to analyse the potential DNA binding of the compound. NMR studies have been carried out on the compounds, in order to understand the structural properties and the species form in solution during the in vitro cell assays. Abstract

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The detection, isolation, and identification of the impurities in the technical grade of the insecticide thiofanox are described. A 13C NMR method was employed to detect impurities at about the 0.1% level or greater. The 13C spectrum of very high signal-to-noise ratio of an impurity concentrate was used to guide subsequent separation and identification work. The sensitivity and reliability of this approach are discussed. Preparative and semipreparative high performance liquid chromatography was employed to isolate 39 nonvolatile components. These were identified on the basis of spectral data and by comparisons with authentic samples which were synthesized when necessary. Some stereochemical assignments are made on the basis of NMR chemical shifts. An additional 30 volatile components were isolated and identified by vacuum distillation and gas chromatography/ mass spectrometry.

Deuterium labeling and high resolution mass spectroscopy have been used to determine the modes of electron impact fragmentation of 3,3-dmethyl-l-methyIthio-2-butanone 0-[ (methylamino)carbonyI]oxime, thiofanox and its metabolites, the sulfoxide and sulfone. The mass spectra of the corresponding oximes were also examined. The carbamates fragmented chiefly by two competing patbways-the loss of CH,N=C-O or the sulfur-containing moiety. The favored process was dependent on the oxidation state at sulfur. Several unusual rearrangements were noted.