Thirty-six substituted phenyl 2-propynyl ethers and thioethers were tested for synergistic activity toward carbaryl in the housefly. The most active compounds, namely the 2,3,6-trichloro, 2,4-dibromo, 2-nitro, 3-nitro, and 2-nitro-4-chlorophenyl 2propynyl ethers lowered the LD50 for carbaryl to less than 0.1 ag per fly. Substitution with more than one nitro group or more than three halogens decreased activity, as did the introduction of an alkyl, alkoxy, or aryl group or the formation of a thioether.
Summa~y. The diphenol 1 was resolved into its antipodes and tlicir absolute configuration was established. The lcvorotatory isomer R-( -)-1 was oxidized t o thc dienone I?-( -) -6 , which was rearrangcd t o afford natural (-)-niultifloraminc ( R -( -)-7), thus cstablishing that tlic latter has the R-configuration. By the same reaction sequcnccs, the enantiomeric diphcnol S-( + )-1 was transformed t o provide (+ )-multifloramine (S-( + )-7) of the S-configuration.
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