title: Identification and synthesis of a male-produced pheromone for the neotropical root weevil Diaprepes abbreviatus.
abstract: An unsaturated hydroxy-ester pheromone was isolated from the headspace and feces of male Diaprepes abbreviatus, identified, and synthesized. The pheromone, methyl (E)-3-(2-hydroxyethyl)-4-methyl-2-pentenoate, was discovered by gas chromatography-coupled electroantennogram detection (GC-EAD), and identified by gas chromatography-mass spectrometry (GC-MS) and nuclear magnetic resonance spectroscopy (NMR). The synthesis yielded an 86:14 mixture of methyl (E)-3-(2-hydroxyethyl)-4-methyl-2-pentenoate (active) and methyl (Z)-3-(2-hydroxyethyl)-4-methyl-2-pentenoate (inactive), along with a lactone breakdown product. The activity of the synthetic E-isomer was confirmed by GC-EAD, GC-MS, NMR, and bioassays. No antennal response was observed to the Z-isomer or the lactone. In a two-choice olfactometer bioassay, female D. abbreviatus moved upwind towards the synthetic pheromone or natural pheromone more often compared with clean air. Males showed no clear preference for the synthetic pheromone. This pheromone, alone or in combination with plant volatiles, may play a role in the location of males by female D. abbreviatus.
authors.affiliation: Agriculture Research Service, United States Department of Agriculture, U. S. Horticultural Research Laboratory, 2001 South Rock Road, Fort Pierce, FL 34945, USA. stephen.lapointe@ars.usda.gov
authors.forename: Stephen L
authors.initials: SL
authors.lastname: Lapointe
authors.forename: Rocco T
authors.initials: RT
authors.lastname: Alessandro
authors.forename: Paul S
authors.initials: PS
authors.lastname: Robbins
authors.forename: Ashot
authors.initials: A
authors.lastname: Khrimian
authors.forename: Ales
authors.initials: A
authors.lastname: Svatos
authors.forename: Joseph C
authors.initials: JC
authors.lastname: Dickens
authors.forename: Fernando
authors.initials: F
authors.lastname: Otálora-Luna
authors.forename: Fatma
authors.initials: F
authors.lastname: Kaplan
authors.forename: Hans T
authors.initials: HT
authors.lastname: Alborn
authors.forename: Peter E
authors.initials: PE
authors.lastname: Teal
mesh_terms: D000818:Animals; D005243:Feces / Q000737:chemistry; D005260:Female; D008297:Male; D012724:Sex Attractants / Q000032:analysis* / Q000096:biosynthesis / Q000138:chemical synthesis* / Q000494:pharmacology; D012726:Sexual Behavior, Animal / Q000187:drug effects; D048889:Weevils / Q000378:metabolism*
chemical_list: D012724:Sex Attractants