Synthesis of Substituted Alkoxy Benzene Minilibraries, for the Discovery of New Insect Olfaction or Gustation Inhibitors

Abstract

We describe methods for the rapid generation of minilibraries of substituted alkoxy benzenes (consisting of 4-5 compounds), for screening as insect olfaction or gustation inhibitors. Synthetic or commercially available monoalkoxy benzene compounds were mixed and reacted with various alkyl halides to afford a first set of minilibraries. A second and third set were generated from allyloxy minilibraries via the Claisen rearrangement and subsequent alkylation of the ortho-allyl phenols. We have chosen to prepare a collection of small libraries (as opposed to one large library) to test the response insects exhibit toward blends of compounds. We demonstrate how our minilibraries can be screened, both against insect antennae and against expressed pheromone-binding proteins from the gypsy moth, Lymantria dispar.

Can We Disrupt the Sensing of Honey Bees by the Bee Parasite Varroa destructor?

“…The dialkoxybenzenes were synthesized as described in Paduraru et al [17], whereas the alicyclic ethers, cy { R 1 ,R 2 }, were synthesized as described in Chen et al [18] and in Chen and Plettner [27]. Library HC 2–169 was “Library C1” from Chen et al [18].…”

“…In view of limited success in exploiting hive semiochemicals in Varroa control, the use of synthetic disruptive compounds can be another approach to confront the mite [16]. Recently, a library of volatile compounds was developed for the disruption of chemical detection by the gypsy moths' antenna [17], [18]. These chemicals apparently interact with the pheromone binding proteins and/or other components of the olfactory system and take an effect only in the presence of a positive chemical stimulus [17], [19], [20].…”

“…Recently, a library of volatile compounds was developed for the disruption of chemical detection by the gypsy moths' antenna [17], [18]. These chemicals apparently interact with the pheromone binding proteins and/or other components of the olfactory system and take an effect only in the presence of a positive chemical stimulus [17], [19], [20]. As the chemical environment of the hive is rich in volatiles, it was interesting to explore the effect of these compounds on host detection and behavior of the Varroa mite.…”

Combinatorial chemistry in the agrosciences

“…The average purity was 78% and 4.4% of the oxime ethers were shown to be muscarinic agonists, including the insecticidally active thiadiazole 24. 25 A series of small libraries designed to interfere with insect olfaction or gustation have recently been reported by Padrurau et al 32 The libraries were made up of variously substituted alkoxy benzenes, some of which were synthesised via a Claisen rearrangement (Scheme 10). Analogues 25 showed significant inhibition of the antennal response to the gypsy moth sex attractant pheromone (+)-disparlure at high doses.…”

Primula spectabilis Tratt. aerial parts: Morphology, volatile compounds and flavonoids

“…The elevated production of benzenoids with a different structure (alkoxybenzenes) with respect to those synthesized by the flower is noteworthy. They may be involved in the chemical defence of leaves, both as repellent against herbivorous and as attractant for parasitoids, as well as allelopathic agents (Akhtar et al, 2007;Paduraru et al, 2008;Pettersson and Boland, 2003).…”