This investigation was supported in part by research grants from the Shell Development Co. and the Division of Biology and Medicine,

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ZULALIAN, GATTERDAMalously with the glucosyl bromide to give N-alkylation or phenyl alkylation was eliminated, for either possibility would result in a product containing a phenolic group. The absence of an aromatic hydroxyl was demonstrated by determining the uv spectra in neutral and in basic solution. Whereas the absorption maxima of 1 and 2 were shifted in the presence of sodium hydroxide, no shift occurred in the uv maxima of 5, 6, or indeed chlorpropham itself.The Michael synthesis is known to yield ß-rather than -glucosides. Confirmation of the ß configuration of compounds 3, 4, 5, and 6 was obtained by determining their specific optical rotations. These rotations, ranging from -39°to -69°, were in the range of values of the ß isomers of known substituted phenyl glucosides and their tetraacetates (-103°t o +45°) rather than in the range of the corresponding a isomers (+137°to + 212°) (Bonner et al., 1952). The susceptibility of 5 and 6 to hydrolysis by the enzyme, /3-glucosidase, also indicates ß configuration. Efforts to confirm the configuration of 3, 4, 5, and 6 by their nmr spectrum were unsuccessful. The H-l' doublet could not be observed because of signal overlap and difficulties with radiofrequency saturation.The mass spectrum of 3 showed mass peaks corresponding to those reported by Still and Mansager (1972) for a sample of acetylated chlorpropham conjugate from soybeans.ed. His procedure involved the reduction of commercially available p-nitrophenyl-/3-glucuronide, followed by reaction with isopropyl chloroformate. ACKNOWLEDGMENTThe author is indebted to Derek Horton of Ohio State University for many helpful suggestions on these syntheses and to the following PPG Industries staff for their part in this work: Kenneth Dress (uv determinations), James Gregory (synthesis of 1), Robert Pfost (mass spectra interpretation), Robert Shupe (ir and nmr determinations), Albert Strong (synthesis of 2), and Jerome Wiedmann (enzymatic hydrolysis studies).

Tests with the radioactive insecticide confirmed the lack of significant residues in the milk and tissues and showed that it is rapidly detoxified and excreted as dimethyl phosphoric acid. Calves showed a similar sensitivity., -Dimethyl I -carbomethoxy-1 -propen-2-yl phosphate was hydrolyzed by cow, calf, and human plasma to yield dimethyl phosphoric acid.

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