Sugar derivatives containing oxiranes and α,β‐unsaturated γ‐lactones as potential environmentally friendly insecticides

Abstract

A range of novel sugar derivatives containing oxiranes or alpha,beta-unsaturated gamma-lactones in their structure were evaluated as potential insecticides with the added possible benefit of being benign in the environment. A number of arthropod species were chosen to represent those in the terrestrial, aerial and aquatic environments, covering target adult insects such as Musca domestica L (housefly) and Trialeurodes vaporariorum (Westwood) (glasshouse whitefly), which are public health and horticultural pests, Drosophila melanogaster Meig (fruitfly), both adult and larva, and a marine non-target crustacean, Artemia salina L. The tested compounds possessed efficacy and selectivity against these insect species, but were not toxic to brine shrimps, a reference organism in assays to evaluate the potential toxicity hazard to invertebrates in ecosystems.

Electrospray ionization mass spectrometric analysis of newly synthesized α,β‐unsaturated γ‐lactones fused to sugars

“…The deprotonated molecule, m/z 171, can also lose 46 Da, attributed to HCOOH, through the cleavage of the C 5 ÀO and C 2 ÀC 1 bonds, to afford the 1,5 A-type ion at m/z 125 (more details on this fragmentation are presented in Scheme S2 of the Supporting Information). The 1,5 A-type ion has been detected for a wide variety of saccharide derivatives including steroidal glycosides 37 and permethylated oligosaccharides, 36 as well as glycoproteins 38 and sulfated heparins.…”

“…This ion shows a greater tendency to fragment than the m/z 171 ion of deprotonated 1, as shown by its lower relative abundance (about 26%). The loss of 46 Da from the deprotonated molecule, attributed to HCOOH, is one of the major fragmentation pathways and affords the 1,5 A-type ion at m/z 155 (more details on this fragmentation are presented in Scheme S3 of the Supporting Information).…”

Exploitation of Furanoid 5‐Azido‐3‐C‐Branched‐Chain Sugars Towards Highly Functionalized Nitrogen‐Containing Carbohydrate Derivatives

“…[6] In particular, some furanose C-C-linked α,β-unsaturated γ-lactones have been described as antifungal [7] and potent insecticidal agents. [8] This biological profile prompted the acquisition of pyranose-fed butenolides [9] and related thiosugar hybrid molecules. [10] These bicyclic compounds were synthesized by a strategy involving the Wittig olefination of appropriately protected pento-or hexofuranos-3-ulose derivatives and subsequent acid hydrolysis of the intermediate furanose-3-C-branched α,β-unsaturated esters (Scheme 1).…”

Furanose C—C‐linked γ‐lactones: a combined ESI FTICR MS and semi‐empirical calculations study

“…[1,2] Compounds with lactones of this type appear throughout the plant kingdom from the simple metabolites of lichens and fungi to the steroidal glycosides, and were even found in animal species such as sponges and insects. [3] This moiety confers a wide variety of biological properties such as cytotoxic, [4 -7] antifeeding, [8] phytotoxic and antibacterial, [9] antifungal, [10] insecticidal, [11] antiinflammatory, [12] and analgesic effects. [13] There are reports in the literature describing the potential use of compounds with this moiety as antitumor agents, [7,12] phospholipase A2 and cyclooxygenase inhibitors, [9] and antibiotics.…”