Suk-Ku Kang

Synthesis and Biological Activity Test of the Sex Pheromone of the Summer Fruit Tortrix Moth

Synthesis and biological activity test are described for the (Z)-9-tetradecen-1-yl acetate(1) and (Z)-11-tetradecen-1-yl acetate(1) and (Z)-11-tetradecen-1-yl acetate(2), the sex pheromone of the summer fruit tortrix moth, Adoxophyes orana. 8-Bromoctan-l-ol THP ether was prepared from 8-bromoctan-l-ol. The lithium anion of 1-hexyne was alkylated with 8-bromoctan-l-ol THP ether gave 9-tetradecyn-l-ol THP ether. Catalytic hydrogenation over Pd/BaSO4 followed by deprotection afforded (Z)-9-tetradecen-l-ol. Acetylation gave (Z)-9-tetradecen-1-yl acetate(1). l0-Bromodecan-l-ol THP ether was obtained from l0-bromodecan-l-ol. In liquid ammonia with THF and HMPA as cosolvents, sodium acetylide could be alkylated with 10-bromodecan-l-ol THP ether to give 11-dodecyn-l-ol THP ether. 11-Dodecyn-l-ol THP ether was then treated with n-BuLi in THF to give the lithium acetylide, which was alkylated with bromoethane to afford 11-tetradecyn-l-ol THP ether. Catalytic hydrogenation, deprotection, and acetylative gave (Z)-11-tetradecen-1-yl acetate(2). The synthetic pheromone thus obtained was attractive to the males of the summer fruit tortrix in the field.

Synthesis and Biological Activity Test of the Sex Pheromone of the Diamond Back Moth

Synthesis and biological activity test are described for the (Z)-11-hexadecen-1-ol, (Z)-11-hexadecen-1-yl acetate, and (Z)-11-hexadecen-l-al, the sex pheromone of the diamond back moth, Plutella xylostella L.. Lithium acetylide was alkylated with 10-bromodecan-1-ol THP ether to give 11-hexadecyn-l-ol THP ether. 11-Hexadecyn-l-ol THP ether was stereoselectively reduced over Pd/BaSO4to yield (Z)-11-hexadecen-l-ol THP ether, which was in turn deprotected to provide (Z)-11-hexadecen-l-ol. (Z)-11-Hexadecen-l-ol was acetylated and oxidized to afford (Z)-11-hexadecen-1-yl acetate and (Z)-11-hexadecen-l-al, respectively. Biological activity test of the synthetic compounds, (Z)-11-hexadecen-l-ol, (Z)-11-hexadecen-1-yl acetate, and (Z)-11-hexadecen-l-al in the ratio of 0.1 : 5 : 5 was tested in the field using polyethylene capsules as containers. The numbers of moth trapped with pheromone vials were counted.

Synthesis and Biological Activity Test of the Pheromone of the Asiatic Leafroller Moth

Synthesis and Biological activity test are described for the (E)-11-tetradecen-1-yl acetate and (Z)-11-tetradecen-1-yl acetate, the sex pheromone of the Asiatic leafroller moth (Archippus breviplicanus Walsingham). 10-Bromodecan-1-ol THP ether was prepared from 10-bromodecan-1-ol. In liquid ammonia with THF and HMPA as cosolvents, sodium acetylide could be alkylated with 10-bromodecan-1-al THP ether to give 11-dodecyn-1-ol THP ether. 11-Dodecyn-1-ol THP ether was then treated with n-Buli in THF to give the lithium acetylide, which was alkylated with bromoethane to afford 11-tetradecyn-1-ol THP ether. 11-Tetradecyn-1-ol THP ether was then reduced over and with Na in liquid to give (Z)-11-tetradecen-1-ol THP ether and (E)-11-tetradecen-1-ol THP ether, respectively. (Z)-and (E)-11-Tetradecen-1-ol THP ether thus obtained were deprotected by refluxing in the presence of PPTS and ethanol. (Z)-and (E)-11-tetradecen-1-ol were acetylated with acetic anhydride to afford the final products, (Z)-11-tetradecen-1-yl acetate (1) and (E)-11-tetradecen-1-yl acetate (2), respectively. The synthetic pheromone thus obtained was attractive to the males of the Asiatic leafroller moth in the field.