Synthesis and herbicidal activity of modified monoterpenes structurally similar to cinmethylin

The preemergence herbicide cinmethylin is a benzyl ether derivative of the monoterpene 1,4-cineole. Other oxygenated monoterpenes (carvone, citronellol, fenchone, geraniol, and pulegone) were previously found to inhibit the germination and growth of several weed species while exhibiting low phytotoxicity to soybean. Benzyl ether derivatives of these oxygenated monoterpenes were synthesized and examined for preemergence and postemergence activity towards corn, soybean, wheat, and velvetleaf. Benzyl pulegyl ether exhibited the most preemergence activity when applied directly to the soil, completely inhibiting wheat and velvetleaf emergence at 1.0 kg ha(-1) while reducing soybean emergence 80%. Several of the benzyl ethers were more inhibitory to velvetleaf radicle elongation relative to cinmethylin but less inhibitory to corn and wheat radicle elongation in petri dish bioassays. Several of the benzyl ethers exhibited limited postemergence activity when applied at 1.0 kg ha(-1) to seedlings of the test species 10 d after emergence. The benzyl ether derivatives demonstrated altered selectivity and sensitivity as compared to the parent compounds and cinmethylin.