Diparopsis castanea

The ate complex (2) of allyl phenyl selenide reacts somewhat less regioselectively than 1. Even so, it was useful for a synthesis of the pheromone (3) of Diparopsis castanea (equation II).2... 

Tertiary pheromonal blends have been identified in two noctuid moths. The red bollworm, Diparopsis castanea, emits dodecyl acetate, (E)-9-dodecenyl acetate, 11-dodecenyl acetate, and (E)-9,ll-dodecadienyl acetate as a sex pheromone, whereas Spodoptera littoral is utilizes a blend made up of tetradecyl acetate, (E)-9-tetradecenyl acetate, (E)-ll-tetradecenyl acetate, and (Z,E)-9,ll-tetradecadieny1 acetate (89). For both species, the conjugated dienes are the most potent olfactory stimulants. 

Anion (64) generally reacts with carbonyl compounds at the y-position, whereas it reacts with alkyl halides at the a-position. The triethylaluminum ate complex of (64) exhibits reversed regioselectivity propanal and 2-methylpropanal give exclusively the a-adducts. The anti isomers are produced predominantly. Organic halides and trimethylsilyl chloride do not react with the aluminum ate complex. 9,11-Dodecadien-l-yl acetate, a pheromone of Diparopsis castanea, is prepared by condensation of 9-oxonon-l-yl acetate via the ate complex (Scheme 43). 

Ac [50767-78-7]. Major sex pheromone of the red boll-worm moth Diparopsis castanea. Bpo.5 108-110°,... 

Ac [35153-10-7]. Pheromone for various moths, esp. A. orana and Diparopsis castanea. 

The 1-phenoxyoctadiene can be used for the synthesis of 12-acetoxy-l,3-dodecadiene (Equation 12), a pheromone of Diparopsis castanea [13]. In this synthesis, the elimination of the phenol yields the required conjugated diene system. 

A number of conjugated dienes have been identified as sex pheromones. Among these are (8 ,10 )-8,10-dodecadien-l-ol (475, Scheme 84) from the codling moth (Laspeyresia pomonella), (7 , 9Z)-7,9-dodecadien-1-yl acetate (490, Scheme 86) from the European grapevine moth (Lobesia botrana), ( )- and (Z)-9,ll-dodecadien-l-yl acetates (518a and 518b, respectively, see Scheme 90) from the red bollworm moth (Diparopsis castanea), and (10 , 12Z)-10,12-hexadecadien-l-ol (498, Scheme 87) from the silkworm moth (Bombyx mori). 

Another cotton pest in several parts of the world is the red boll-worm, Diparopsis castanea. Its pheromone and an inhibitor have been shown to disrupt mating, but no crop damage assessment was made (607). 

Marks, R. J. The influence of behavior modifying chemicals on mating success of the red bollworm, Diparopsis castanea Hmps. (Lepidoptera Noctuidae) in Malawi. Bull. Entomol. Res. 66, 279—300 (1976). 

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