Synthesis and physiological activity of (S)-d-perilla thioesters (part 2)

Synthesis and physiological activity of thioester compounds with a perilla residue were examined. (S)-d-Perilla nitriles (S)-2 were prepared by variou s methods and converted to (S)-d-perillic acid (S)-3 by hydrolysis. The aci d were condensed with several thiol compounds to obtain thioester compounds (S)-3a-(S)-3j in 15-56% yield in three steps, the first being the imidatio n of (S)-d-perillaldehyde (S)-1. The ten perilla derivatives obtained were tested for miticidal activity and antimicrobial activity in plants. The mit icidal activities of these thioester compounds (S)-3a-(S)-3j toward Tyropha gus putrescentiae and Dermatophagoides farinae were measured. On filter pap er, these thioester compounds (S)-3a and (S)-3g had higher miticidal activi ty than N,N-diethyl-m-toluamide (DEET) for D. farinae. The antimicrobial ac tivities of these thioester compounds (S)-3a-(R)-3j toward Pyricularia oryz ae, Phytophthora infestans, Rhizoctonia solani, Pythium debaryanum, and Bot rytia cinerea were measured. On disks, these thioester compounds (S)-3a-(R) -3j had as good antimicrobial activity as reference compounds for Pyricular ia oryzae and Phytophthora infestans.