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Insecticidal efficacy of six new pyrrole derivatives against four stored-product pests

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Abstract

Several pyrrole derivatives exhibit insecticidal activity and can be effective as grain protectants. In the present study, we evaluate the insecticidal efficacy of six novel pyrrole derivatives, namely methyl 3-(methylthio)-4,6-dioxo-5-phenyl-1,3a,4,5,6,6a-hexahydropyrrolo[3,4-c]pyrrole-1 carboxylate (compound syn) (2a-syn), methyl 3-(methylthio)-4,6-dioxo-5-phenyl-1,3a,4,5,6,6a-hexahydropyrrolo[3,4-c]pyrrole-1-carboxylate (compound anti) (2a-anti), methyl 3-(benzylthio)-4,6-dioxo-5-phenyl-1,3a,4,5,6,6a-hexahydropyrrolo[3,4-c]pyrrole-1-carboxylate (compound syn) (2f-syn), methyl 3-(benzylthio)-4,6-dioxo-5-phenyl-1,3a,4,5,6,6a-hexahydropyrrolo[3,4-c]pyrrole-1-carboxylate (compound anti) (2f-anti), methyl 3-(butylthio)-4,6-dioxo-5-phenyl-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrrole-1-carboxylate (3e), and methyl 2-benzyl-3-(methylthio)-4,6-dioxo-5-phenyl-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrrole-1-carboxylate (0665), against four important species infesting stored products, the rice weevil, Sitophilus oryzae (Coleoptera: Curculionidae), the lesser grain borer, Rhyzopertha dominica (Coleoptera: Bostrychidae), the confused flour beetle, Tribolium confusum (Coleoptera: Tenebrionidae), and the Mediterranean flour moth, Ephestia kuehniella (Lepidoptera: Pyralidae). The six pyrrole derivatives were evaluated on wheat at different doses (0.1, 1, and 10 ppm) and exposure intervals (7, 14, and 21 days). For S. oryzae adults, the highest mortality was recorded at 10 ppm of 2a-syn (36.7%) followed by 2f-syn (32.2%) and 2f-anti (27.8%) after 21 days of exposure. Regarding progeny production, the application of the six pyrrole derivatives significantly reduced offspring emergence if compared with the controls. After 21 days, mortality of R. dominica reached 50% testing 10 ppm of 2f-syn, followed by 2a-syn (46.7%), 2f-anti (41.1%), and 2a-anti (33.3%), while for 3e and 0665, mortality remained low, not exceeding 17.8%. Mortality of T. confusum adults was very low, ranging from 0 to 16.7% after 21 days of exposure. Progeny production was low (< 1.7 individuals per vial) for all doses of the tested pyrrole derivatives, including control vials. For 2a-syn, 2a-anti, 2f-anti, and 0665, no progeny production was recorded testing 1 and 10 ppm, while for 2f-syn and 3e, no offspring emergence was noted testing 10 ppm. For T. confusum larvae, after 21 days of exposure, mortality reached 62.2% testing 10 ppm of 3e followed by 0665 (55.6%) and 2a-anti (42.2%). For E. kuehniella larvae, mortality reached 57.8% at 10 ppm of 2a-syn, followed by the pyrrole derivative 2f-anti (43.3%) after 21 days of exposure. Overall, these results show that the efficacy of pyrrole derivatives strongly varied according to the exposure interval, tested dose, treated insect species and developmental instar. The tested pyrrole derivatives, with special reference to 2a-syn, 2a-anti, 2f-syn, 2f-anti and 0665, are slow-acting compounds exerting relevant toxicity on key stored-product pests over time. They can be considered further for assays with selected blends aiming to develop novel control tools against stored-product pests in real-world conditions.

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Acknowledgments

This study was partially supported by the scholarship “Athanassios Sotiroudas” provided by the Hellenic Entomological Society.

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Authors and Affiliations

  1. Laboratory of Agricultural Zoology and Entomology, Department of Crop Science, Agricultural University of Athens, 75 Iera Odos str., 11855, Athens, Attica, Greece

    Maria C. Boukouvala & Nickolas G. Kavallieratos

  2. Laboratory of Organic Chemistry, Department of Chemistry, University of Ioannina, Panepistimioupolis, 45110, Ioannina, Greece

    Maria C. Boukouvala & Lazaros P. Hadjiarapoglou

  3. Laboratory of Entomology and Agricultural Zoology, Department of Agriculture Crop Production and Rural Environment, University of Thessaly, Phytokou str., 38446, Nea Ionia, Magnisia, Greece

    Christos G. Athanassiou

  4. Department of Agriculture, Food and Environment, University of Pisa, via del Borghetto 80, 56124, Pisa, Italy

    Giovanni Benelli

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  1. Maria C. Boukouvala
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  2. Nickolas G. Kavallieratos
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Correspondence to Nickolas G. Kavallieratos.

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Boukouvala, M.C., Kavallieratos, N.G., Athanassiou, C.G. et al. Insecticidal efficacy of six new pyrrole derivatives against four stored-product pests. Environ Sci Pollut Res 26, 29845–29856 (2019). https://doi.org/10.1007/s11356-019-05961-x

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