Synthesis, Functional Assays, Electrophysiological Activity, and Field Tests of Pheromone Antagonists of the Tomato Leafminer, Tuta absoluta

J Agric Food Chem. 2016 May 11;64(18):3523-32. doi: 10.1021/acs.jafc.6b00674. Epub 2016 Apr 27.

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.

Keywords: Tuta absoluta; electrophysiology; field tests; functional assays; pheromone antagonists; synthesis; tomato leafminer.

MeSH terms

  • Animals
  • Electrophysiology
  • Female
  • Insecticides / chemical synthesis*
  • Insecticides / chemistry
  • Insecticides / pharmacology*
  • Male
  • Moths / drug effects*
  • Moths / physiology
  • Plant Diseases / parasitology
  • Sex Attractants / chemical synthesis*
  • Sex Attractants / chemistry
  • Sex Attractants / pharmacology*
  • Solanum lycopersicum / parasitology

Substances

  • Insecticides
  • Sex Attractants