title: Synthesis, Functional Assays, Electrophysiological Activity, and Field Tests of Pheromone Antagonists of the Tomato Leafminer, Tuta absoluta.
abstract: The tomato leafminer, Tuta absoluta, is one of the major pests of tomato and other Solanaceae in many regions worldwide. In the search for new strategies to control this pest, we present herewith the stereoselective synthesis, electrophysiological activity, functional analysis, and field tests of new chemicals as possible antagonists of the sex pheromone of the leafminer. The chemicals are methyl ketone (MK) and trifluoromethyl ketone (TFMK) structural analogues of both components of the pheromone. Most of the chemicals exerted per se some electrophysiological activity and inhibited the electroantennographic response to the pheromone when vapors of the inhibitor were passed over the antennae. Except TFMK 3, which elicited a modest effect, the compounds did not exhibit antiesterase activity on the pheromone-degrading enzymes of the antennae, but in the field the chemicals, particularly MK 5, notably decreased the number of catches when mixed with the pheromone in 1:1 and 10:1 ratios, regardless the infestation level of the plot. These results suggest that MK 5 is a good behavioral antagonist of the pheromone to be considered as a putative agent to control the pest in new future integrated pest management (IPM) strategies.
authors.affiliation: Department of Biological Chemistry and Molecular Modelling, Institute of Advanced Chemistry of Catalonia (CSIC) , Jordi Girona 18-26, 08034 Barcelona, Spain.
authors.forename: Aroa
authors.initials: A
authors.lastname: Dominguez
authors.affiliation: Department of Biological Chemistry and Molecular Modelling, Institute of Advanced Chemistry of Catalonia (CSIC) , Jordi Girona 18-26, 08034 Barcelona, Spain.
authors.forename: Marc
authors.initials: M
authors.lastname: Puigmartı́
authors.affiliation: Department of Biological Chemistry and Molecular Modelling, Institute of Advanced Chemistry of Catalonia (CSIC) , Jordi Girona 18-26, 08034 Barcelona, Spain.
authors.forename: M Pilar
authors.initials: MP
authors.lastname: Bosch
authors.affiliation: Department of Pharmacology and Therapeutic Chemistry, Unit Associated to CSIC, Faculty of Pharmacy, University of Barcelona , Avinguda Diagonal s/n, 08028 Barcelona, Spain.
authors.forename: Gloria
authors.initials: G
authors.lastname: Rosell
authors.affiliation: Department of Biological Chemistry and Molecular Modelling, Institute of Advanced Chemistry of Catalonia (CSIC) , Jordi Girona 18-26, 08034 Barcelona, Spain.
authors.forename: Ramon
authors.initials: R
authors.lastname: Crehuet
authors.affiliation: Department of Inorganic and Organic Chemistry, EPSL, University of Jaén , Linares (Jaén), Spain.
authors.forename: Antonio
authors.initials: A
authors.lastname: Ortiz
authors.affiliation: Department of Biological Chemistry and Molecular Modelling, Institute of Advanced Chemistry of Catalonia (CSIC) , Jordi Girona 18-26, 08034 Barcelona, Spain.
authors.forename: Carmen
authors.initials: C
authors.lastname: Quero
authors.affiliation: Department of Biological Chemistry and Molecular Modelling, Institute of Advanced Chemistry of Catalonia (CSIC) , Jordi Girona 18-26, 08034 Barcelona, Spain.
authors.forename: Angel
authors.initials: A
authors.lastname: Guerrero
mesh_terms: D000818:Animals; D004594:Electrophysiology; D005260:Female; D007306:Insecticides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D018551:Solanum lycopersicum / Q000469:parasitology; D008297:Male; D009036:Moths / Q000187:drug effects* / Q000502:physiology; D010935:Plant Diseases / Q000469:parasitology; D012724:Sex Attractants / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D007306:Insecticides; D012724:Sex Attractants
keywords: Tuta absoluta; electrophysiology; field tests; functional assays; pheromone antagonists; synthesis; tomato leafminer