1992 Volume 66 Issue 12 Pages 1771-1777
The monoterpene aldehydes (-)-myrtenal, (-)-perillaldehyde, and (+)-α-campholenic aldehyde were converted to nitriles by sequential N, N-dimethylhydrazonation, methylation, and an elimination reaction of the Hofmann-type. The nitriles were converted to terpenoyl chlorides by hydrolysis and chlorination with thionyl chloride. The chlorocarbonylated terpenes were condensed with pyrrolidine, 2-, 3-, or 4-methylpiperidines, and 2, 6- or 3, 5-dimethylpiperidines to obtain 21 terpene amides in 11_??_36% overall yields for the four steps starting from the imidation of the terpene aldehydes.
The bactericidal and fungicidal activities of these amides toward Puccinia recondita ROBERGE (wheat leaf rust), Phytophthora infestans (MONT.) de BARY, and Erysiphe graminis D. C. (f. sp. tritici MARCHAL). 2, 6-Dimethyl-1-[2-(2, 2, 3-trimethyl-cyclopentyl-3-ene) acetoyl] piper idine at 300 ppm prevented the growth of Puccinia recondita ROBERGE in a pot test. When used to treat Disbrotica longicornis SAY, Spodoptera frugiperda J. E. SMITH, and Tetranychus urticae KOCH, 1-(6, 6-dimethylbicyclo-[3.1.1] hepto-2-ene-2-carbonyl)-2-methylpiperidine at 300 ppm almost completely eradicated Disbrotica longicornis SAY (corn rootworm) in soil treated with the amide. 1-(4-Isopropenyl-l-cyclohexene-l-carbonyl) pyrrolidine at 300 ppm inhibited the germination and growth of Lycopersicon esculentum MILL. (tomato), but had no effect on Echinochloa crus-galli BEAUV., Setaria viridis BEAUV., Tagetes sp.; and Abutilon theophrasti MODIK. The other amides at the concentration of 300 ppm had little or no activity.
