Synthetic amides toxic to the leaf‐cutting ant Atta sexdens rubropilosa L. and its symbiotic fungus

Abstract

1 Nine synthetic amides similar to natural N-piperidine-3-(4,5-methylenedioxyphenyl)-2-(E)-propenamide and N-pyrrolidine-3-(4,5-methylenedyoxiphenyl)-2-(E)-propenamide were synthesized and identified by their spectroscopic data. 2 The toxicity of these synthetic amides to the Atta sexdens rubropilosa workers and the antifungal activity against Leucoagaricus gongylophorus, the symbiotic fungus of the leaf-cutting ants, were determined. 3 Workers ants that were fed daily on an artificial diet to which these compounds were added had a higher mortality rate than the controls for N-pyrrolidine-3-(3 0 ,4 0 -methylenedioxyphenyl)-2-(E)-propenamide and N-benzyl-3-(3 0 ,4 0 -methylenedioxyphenyl)-2-(E)-propenamide at a concentration of 100 mg/mL. 4 The completely inhibition (100%) of the fungal growth was observed with Npiperidine-3-(3 0 ,4 0 -methylenedioxyphenyl)-2-(E)-propenamide and N,N-diethyl-3-(3 0 ,4 0 -methylenedioxyphenyl)-2-(E)-propenamide at concentrations of 50 and 100 mg/mL and N-pirrolidine-3-(3 0 ,4 0 -methylenedioxyphenyl)-2-(E)-propenamide at a concentration of 100 mg/mL. 5 The possibility of controlling these insects in the future using synthetic piperamides that can simultaneously target both organisms is discussed.

Isobutyl amides—potent compounds for controlling Diatraea saccharalis

“…Moreover, these substances have demonstrated potent effects on, for example, cowpea weevil ( Callosobruchus maculatus F.), rice weevil ( Sitophilus orizae L.), adzuki bean weevil ( C. chinensis L.), houseflies ( Musca domestica L.) and mosquito ( Aedes atropalpus Coq. ), as well as leaf‐cutting ants ( Atta sexdens rubropilosa Forel) 7–12. These amides show antifungal activities against Leucoagaricus gongylophorus Singer, the symbiotic fungus of leaf‐cutting ants, and phytopathogenic fungi Cladosporium cladosporioides (Fr.)…”

“…These amides show antifungal activities against Leucoagaricus gongylophorus Singer, the symbiotic fungus of leaf‐cutting ants, and phytopathogenic fungi Cladosporium cladosporioides (Fr.) de Vries and C. sphaerospermum Penzig 6, 12–14…”

Plant–Derived Products for Leaf–Cutting Ants Control

“…Compounds 1, 2, 4, 5, 6, 7, and 9 had no effect on the median survival period at any of the concentrations tested (25,50, and 100 µg mL -1 ). At 100 µg mL -1 , compounds 1, 2, and 3 completely inhibited fungal growth, and partial inhibition was observed for compounds 4 (80%), 5 (40%), and 6 (20%), while compounds 7, 8, and 9 had no effect on the growth of the symbiotic fungus [66].…”

Trajectory of Water- and Fat-Soluble Dyes in the Grass-Cutting ant Atta capiguara (Hymenoptera, Formicidae): Evaluation of Infrabuccal Cavity, Post-Pharyngeal Glands and Gaster

“…This knowledge has generated a series of studies in the area of chemical control of leaf-cutting ants, but most are experiments with insecticides that aim to elucidate the dynamic of workers contamination (Echols 1966;Andrade 2002;Pagnocca et al 2006;Santos et al 2006;Nagamoto et al 2007).…”