We demonstrate the generation of fifth-harmonic pulses at 161 nm, with an energy of up to 600 nJ and 160 fs pulse duration from a Ti:sapphire laser at 1 kHz repetition rate by four-wave difference-frequency mixing in argon-filled waveguides. The efficiency is greatly improved by coupling to higher-order transverse modes, as well as by coating the inner surface of the waveguide. A numerical model of the process yields an understanding of the main effects influencing the harmonic generation.