Acyl fluorides as reactive mimics of aldehyde pheromones: hyperactivation and aphrodisiac inHeliothis virescens

Abstract

Substitution of fluorine for the aldehydic hydrogen provides behaviorally active, chemically reactive pheromone mimics. In male moths of the tobacco budworm Heliothis virescens, zg-14:Acf and Zll-16:Acf cause hyperactivity and irreversible extension of the genitalia in over 80 % of treated moths. In addition, a combination of the two components leads to 10-50 % of the pairs involving one treated partner becoming locked in copula.

Behavioral and neurosensory responses of the boll weevil,Anthonomus grandis Boh. (Coleoptera: Curculionidae), to fluorinated analogs of aldehyde components of its pheromone

“…The lack of activity of the acyl fluorides is in contrast with the activity of the acyl fluoride analogs of the aldehyde components of the pheromone of Heliothis virescens (Prestwich et al, 1986). Despite the ease of hydrolysis of saturated acyl fluorides to the corresponding acids, conjugated unsaturated acyl fluorides are quite stable.…”

“…Alternatively, analogs of pheromone molecules have been designed and synthesized and found to inhibit response to the pheromone (Mitchell et al, 1975Camps et al, 1990), enhance response to the pheromone (Camps et al, 1988;Bengtsson et al, 1990), or mimic the pheromone component (Camps et al, 1988;Briggs et al, 1986;Eidmann et al, 1986). The acyl fluoride analogs of Heliothis pheromone components acted as hyperagonists, eliciting aphrodisia and disorientation in male moths (Prestwich et al, 1986).…”

“…Fluorinated analogs of bioactive molecules offer the advantage of isosteric substitution of a fluorine atom for a hydrogen atom while modifying the charge distribution of the molecule by the electrophilic nature of the fluorine atom (Pavlath, 1986;Prestwich, 1986). Fluorinated analogs of various molecules have been synthesized, including potential pesticides (Pavlath, 1986) and naturally occurring compounds such as hormones and pheromones (Briggs et al, 1986;Prestwich, 1986Prestwich, , 1987.…”

“…Fluorinated analogs of various molecules have been synthesized, including potential pesticides (Pavlath, 1986) and naturally occurring compounds such as hormones and pheromones (Briggs et al, 1986;Prestwich, 1986Prestwich, , 1987. Acyl and o~-fluorinated analogs of the aldehyde components of the boll weevil pheromone were synthesized and evaluated for activity in female boll weevils using electroantennograms (EAGs) (Prestwich et al, 1988).…”

An analysis of structure fitting and bioactivity between sex pheromone of cotton bollworm, Helicoverpa armigera (Hübner) and its fluorinated analogs

“…Substitution of fluorine for hydrogen would not induce a significant change in molecular volume or surface area [10] . The bioactivity of fluorinated pheromone analogs has been studied by many scientists [10,12,[14][15][16][17][18][19][20][21][22][23][24][25][26][27] .…”