Hostname: page-component-7dd5485656-wjfd9 Total loading time: 0 Render date: 2025-10-31T12:39:20.111Z Has data issue: false hasContentIssue false
  • English
  • Français

Biological activity of two new pyrrole derivatives against stored-product species: influence of temperature and relative humidity

Published online by Cambridge University Press:  18 April 2016

M.C. Boukouvala ,
N.G. Kavallieratos ,
C.G. Athanassiou  and
L.P. Hadjiarapoglou
M.C. Boukouvala
Affiliation:
Laboratory of Agricultural Zoology and Entomology, Department of Crop Science, Agricultural University of Athens, 75 Iera Odos str., 11855 Athens, Attica, Greece Laboratory of Agricultural Entomology, Department of Entomology and Agricultural Zoology, Benaki Phytopathological Institute, 8 Stefanou Delta str., 14561 Kifissia, Attica, Greece Laboratory of Organic Chemistry, Department of Chemistry, University of Ioannina, Panepistimioupolis, 45110 Ioannina, Greece
N.G. Kavallieratos*
Affiliation:
Laboratory of Agricultural Zoology and Entomology, Department of Crop Science, Agricultural University of Athens, 75 Iera Odos str., 11855 Athens, Attica, Greece Laboratory of Agricultural Entomology, Department of Entomology and Agricultural Zoology, Benaki Phytopathological Institute, 8 Stefanou Delta str., 14561 Kifissia, Attica, Greece
C.G. Athanassiou
Affiliation:
Laboratory of Entomology and Agricultural Zoology, Department of Agriculture Crop Production and Rural Environment, University of Thessaly, Phytokou str., Nea Ionia, 38446 Magnissia, Greece
L.P. Hadjiarapoglou
Affiliation:
Laboratory of Organic Chemistry, Department of Chemistry, University of Ioannina, Panepistimioupolis, 45110 Ioannina, Greece
*
*Author for correspondence Phone: +30-2105294569 E-mail: nick_kaval@hotmail.com
Get access Rights & Permissions [Opens in a new window]

Abstract

Members of the pyrrole group are likely to have interesting properties that merit additional investigation as insecticides at the post-harvest stages of agricultural commodities. In the present work, the insecticidal effect of two new pyrrole derivatives, ethyl 3-(benzylthio)-4,6-dioxo-5-phenyl-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrrole-carboxylate (3i) and isopropyl 3-(benzylthio)-4,6-dioxo-5-phenyl-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrrole-carboxylate (3k) were studied as stored-wheat protectants against two major stored-product insect species, the confused flour beetle, Tribolium confusum Jaquelin du Val adults and larvae and the Mediterranean flour moth, Ephestia kuehniella Zeller larvae at different doses (0.1, 1 and 10 ppm), exposure intervals (7, 14 and 21 days), temperatures (20, 25 and 30°C) and relative humidity (55 and 75%) levels. For T. confusum adults, in the case of the pyrrole derivative 3i, mortality was low and it did not exceed 32.2% in wheat treated with 10 ppm 3i at 30°C and 55% relative humidity. Progeny production was very low (<1 individual/vial) in all combinations of 55% relative humidity, including control. In the case of the pyrrole derivative 3k, mortality reached 67.8% at 30°C and 55% relative humidity in wheat treated with 10 ppm after 21 days of exposure. Progeny production was low in all tested combinations (≤0.7 individuals/vial) of 55% relative humidity, including control. For T. confusum larvae, in the case of the pyrrole derivative 3i, at the highest dose, mortality was 82.2% at 25°C and 55% relative humidity whereas in the case of 3k it reached 77.8% at the same combination. In contrast, mortality at 75% relative humidity remained very low and did not exceed 13.3%. For E. kuehniella larvae, the highest mortalities, 44.4 and 63.3%, were observed in 10 ppm at 25°C and 55% relative humidity for both pyrrole derivatives. The compounds tested here have a certain insecticidal effect, but this effect is moderated by the exposure, the target species, the temperature and the relative humidity.

Keywords

pyrrole derivativesstored-product insectsdoseexposurerelative humiditytemperature

Information

Type
Research Papers
Information
Bulletin of Entomological Research , Volume 106 , Issue 4 , August 2016 , pp. 446 - 456
Check for updates
Copyright
Copyright © Cambridge University Press 2016 

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

Article purchase

Temporarily unavailable

References

Arthur, F.H. (1996) Grain protectants: current status and prospects for the future. Journal of Stored Products Research 32, 293–302.CrossRefGoogle Scholar
Arthur, F.H. (1999) Effect of temperature on residual toxicity of cyfluthrin wettable powder. Journal of Economic Entomology 92, 695–699.CrossRefGoogle Scholar
Arthur, F.H. (2000) Toxicity of diatomaceous earth to red flour beetles and confused flour beetles (Coleoptera: Tenebrionidae): effects of temperature and relative humidity. Journal of Economic Entomology 93, 526–532.Google Scholar
Arthur, F.H. (2004) Evaluation of methroprene alone and in combination with diatomaceous earth to control Rhyzopertha dominica (Coleoptera: Bostrichidae) on stored wheat. Journal of Stored Products Research 40, 485–498.CrossRefGoogle Scholar
Arthur, F.H. (2012) Aerosols and contact insecticides as alternatives to methyl bromide in flour mills, food production facilities, and food warehouses. Journal of Pest Science 85, 323–329.Google Scholar
Arthur, F.H. & Campbell, J.F. (2008) Distribution and efficacy of pyrethrin aerosol to control Tribolium confusum (Coleoptera: Tenebrionidae) in food storage facilities. Journal of Stored Products Research 44, 58–64.CrossRefGoogle Scholar
Arthur, F.H. & Fontenot, E.A. (2012) Food source provisioning and susceptibility of immature and adult Tribolium castaneum on concrete partially treated with chlorfenapyr (Phantom®). Journal of Pest Science 85, 277–282.CrossRefGoogle Scholar
Arthur, F.H., Yue, B. & Wide, G.E. (2004) Susceptibility of stored-product beetles on wheat and maize treated with thiamethoxam: effects of concentration, exposure interval, and temperature. Journal of Stored Products Research 40, 527–546.CrossRefGoogle Scholar
Athanassiou, C.G. & Kavallieratos, N.G. (2014) Evaluation of spinetoram and spinosad for control of Prostephanus truncatus, Rhyzopertha dominica, Sitophilus oryzae and Tribolium confusum on stored grains under laboratory tests. Journal of Pest Science 87, 469–483.Google Scholar
Athanassiou, C.G., Kavallieratos, N.G., Vayias, B.J., Papagregoriou, A.S., Dimizas, C.B. & Buchelos, C.Th. (2004) Residual toxicity of beta cyflurthrin, alpha cypermethrin and deltamethrin against Tribolium confusum Jacquelin du Val (Coleoptera: Tenebrionidae) on stored wheat. Applied Entomology and Zoology 39, 195–202.Google Scholar
Athanassiou, C.G., Arthur, F.H. & Throne, J.E. (2009) Efficacy of grain protectants against four psocid species on maize, rice and wheat. Pest Management Science 65, 1140–1146.Google Scholar
Athanassiou, C.G., Arthur, F.H. & Throne, J.E. (2010 a) Efficacy of layer treatment with methoprene for control of Rhyzopertha dominica (Coleoptera: Bostrychidae) on wheat, rice and maize. Pest Management Science 67, 380–384.Google Scholar
Athanassiou, C.G., Arthur, F.H. & Throne, J.E. (2010 b) Efficacy of methoprene for control of five species of psosids (Psocoptera) on wheat, rice, and maize. Journal of Food Protection 73, 2244–2249.Google Scholar
Athanassiou, C.G., Arthur, F.H., Kavallieratos, N.G. & Throne, J.E. (2011) Efficacy of spinosad and methoprene, applied alone or in combination against six stored-product insect species. Journal of Pest Science 84, 61–71.CrossRefGoogle Scholar
Athanassiou, C.G., Kavallieratos, N.G., Arthur, F.H. & Throne, J.E. (2013) Efficacy of a combination of beta-cyfluthrin and imidacloprid and beta-cyfluthrin alone for control of stored product insects on concrete. Journal of Economic Entomology 106, 1064–1070.CrossRefGoogle ScholarPubMed
Athanassiou, C.G., Kavallieratos, N.G., Arthur, F.H. & Throne, J.E. (2014) Residual efficacy of chlorfenapyr for control of stored-product psocids (Psocoptera). Journal of Economic Entomology 10, 854–859.CrossRefGoogle Scholar
Badii, K.B., Adarkwash, C., Ulrichs, C. & Obeng Ofori, D. (2013) Efficacy of diatomaceous earth formulations against Callosobruchus maculatus (F.) (Coleoptera: Bruchidae) in Kersting's groundnut (Macrotyloma geocarpum Harms): influence of dosage rate and relative humidity. Journal of Pest Science 87, 285–294.CrossRefGoogle Scholar
Bell, C.H. (2000) Fumigation in the 21st century. Crop Protection 19, 563–569.Google Scholar
Benhalima, H., Chaudhry, M.Q., Mills, K.A. & Price, N.R. (2004) Phosphine resistance in stored-product insects collected from various grain storage facilities in Morocco. Journal of Stored Products Research 40, 241–249.Google Scholar
Brewer, M.J. & Ferrell, M.A. (1992) Stored Grain Insects of Wyoming, an Introduction. MP-22. Laramie, WY, Cooperative Extension Service.Google Scholar
Chaudhry, M.Q. (2000) Phoshine resistance: a growing threat to an ideal fumigant. Pesticide Outlook 11, 88–91.CrossRefGoogle Scholar
Cogburn, R.R. (1988) Fenoxycarb as a long-term protectant for stored rough rice. Journal of Economic Entomology 81, 722–726.Google Scholar
Corrêa, A.S., Tomé, H.V.V., Braga, L.S., Martins, G.F., de Olivera, L.O. & Guedes, R.N.C. (2014) Are mitochondrial lineages, mitochondrial lysis and respiration rate associated with phosphine susceptibility in the maize weevil Sitophilus zeamais? Annals of Applied Biology 165, 137–146.Google Scholar
Daglish, G.J. (2008) Impact of resistance on the efficacy of binary combinations of spinosad, chlorpyrifos-methyl and s-methoprene against five stored-grain beetles. Journal of Stored Products Research 44, 71–76.CrossRefGoogle Scholar
Daglish, G.J. & Nayak, M. (2010) Uneven application can influence the efficacy of s-methoprene against Rhyzopertha dominica (F.) in wheat. Journal of Stored Products Research 46, 250–253.Google Scholar
Daglish, G.J. & Wallbank, B.E. (2005) Efficacy of diflubenzuron plus methoprene against Sitophilus oryzae and Rhyzopertha dominica in stored sorghum. Journal of Stored Products Research 41, 353–360.Google Scholar
Daglish, G.J., Erbacher, J.M. & Eelkema, M. (1993) Efficacy of protectants against Callosobruchus phaseoli (Gyll.) and C. maculatus (F.) (Coleoptera: Bruchidae) in mugbeans. Journal of Stored Products Research 29, 345–349.Google Scholar
Edwards, J.P. & Short, J.E. (1984) Evaluation of three compounds with insect juvenile hormone activity as grain protectants against insecticide-susceptible and resistant strains of Sitophilus species (Coleoptera: Curculionidae). Journal of Stored Products Research 20, 11–15.Google Scholar
Fields, P.G. & White, N.D.G. (2002) Alternatives to methyl bromide treatments for stored-product and quarantine insects. Annual Review of Entomology 47, 331–359.Google Scholar
Georgiou, D., Toutountzoglou, V., Muir, K.W., Hadjipavlou Litina, D. & Elemes, Y. (2012) Synthesis of sulfur containing dihydro-pyrrolo derivatives and their biological evaluation as antioxidants. Bioorganic & Medicinal Chemistry 20, 5103–5109.Google Scholar
Hertlein, M.B., Thompson, G.D., Subramanyam, Bh. & Athanassiou, C.G. (2011) Spinosad: a new natural product for stored grain protection. Journal of Stored Products Research 47, 131–146.Google Scholar
Hunt, D.A. (1996) 2-Arylpyrroles: a new class of insecticide. Structure, activity, and mode of action. Pesticides Science 47, 201–202.3.0.CO;2-9>CrossRefGoogle Scholar
Jacob, T.A. & Cox, P.D. (1977) The influence of temperature and humidity on the life-cycle of Ephestia kuehniella Zeller (Lepidoptera: Pyralidae). Journal of Stored Products Research 13, 107–118.CrossRefGoogle Scholar
Jenson, E.A., Arthur, F.H. & Nechols, J.R. (2009) Efficacy of methoprene applied at different temperatures and rates on surface substrates to control eggs and fifth instars of Plodia interpunctella . Journal of Economic Entomology 102, 1992–2002.Google Scholar
Kavallieratos, N.G., Athanassiou, C.G., Vayias, Β.J., Mihail, S. & Tomanović, Ž. (2009) Insecticidal efficacy of abamectin against three stored product insect pests: influence of dose rate, temperature, commodity and exposure interval. Journal of Economic Entomology 102, 1352–1359.Google Scholar
Kavallieratos, N.G., Athanassiou, C.G., Hatzikonstantinou, A.N. & Kavallieratou, H.N. (2011) Abiotic and biotic factors affect efficacy of chlorfenapyr for control of stored-product insect pests. Journal of Food Protection 74, 1288–1299.Google Scholar
Kavallieratos, N.G., Athanassiou, C.G. & Boukouvala, M.C. (2012 a) Insecticidal effect of chlorantaniliprole against major stored-product insect pests in different grain commodities under laboratory tests. Pest Management Science 69, 1141–1154.Google Scholar
Kavallieratos, N.G., Athanassiou, C.G., Vayias, B.J. and Tomanović, Ž. (2012 b) Efficacy of insect growth regulators as grain protectants against two stored-product pests in wheat and maize. Journal of Food Protection 75, 942–950.Google Scholar
Kavallieratos, N.G., Athanassiou, C.G. & Arthur, F.H. (2015 a) Efficacy of deltamethrin against stored-product beetles at short exposure intervals or on a partially treated rice mass. Journal of Economic Entomology 108, 1416–1421.Google Scholar
Kavallieratos, N.G., Athanassiou, C.G., Korunic, Z. & Mikeli, N.H. (2015 b) Evaluation of three novel diatomaceous earths against three stored-grain beetle species on wheat and maize. Crop Protection 75, 132–138.CrossRefGoogle Scholar
Kostyukovsky, M., Chen, B., Atsmi, S. & Shaaya, E. (2000) Biological activity of two juvenoids and two ecdysteroids against three stored product insects. Insect Biochemistry and Molecular Biology 30, 891–897.Google Scholar
McLeod, P., Diaz, F.J. & Johnson, D.T. (2002) Toxicity, persistence, and efficacy of spinosad, chlorfenapyr, and thiamethoxam on eggplant when applied against the eggplant flea beetle (Coleoptera: Chrysomelidae). Journal of Economic Entomology 95, 331–335.Google Scholar
Nayak, M.K., Collins, P.J. & Reid, S.R. (1998) Efficacy of grain protectants and phosphine against Liposcelis bostrychophila, L. entomophila, and L. paeta (Psocoptera: Liposcelididae). Journal of Economic Entomology 91, 1208–1212.Google Scholar
Oikonomou, K., Georgiou, D., Katsamakas, S., Hadjipavlou Litina, D. & Elemes, Y. (2015) Sulfanyl 5H-dihydropyrrole derivatives via 1,3-dipolar cycloassition, their further chemical manipulation and antioxidant activity. Arkivoc 16, 214–231.Google Scholar
Pimentel, M.A.G., Faroni, L.R.D'A., Tótola, M.R. & Guedes, R.N.C. (2007) Phoshine resistance, respiration rate and fitness consequences in stored-product research. Pest Management Science 63, 876–881.CrossRefGoogle Scholar
Pimentel, M.A.G., Faroni, L.R.D'A., Guedes, R.N.C., Sousa, A.H. & Tótola, M.R. (2009) Phosphine resistance in Brazilian populations of Sitophilus zeamais Motschulsky (Coleoptera: Curculionidae). Journal of Stored Products Research 45, 71–74.Google Scholar
Pimentel, M.A.G., Faroni, L.R.A., Corrêa, A.S. & Guedes, R.N.C. (2012) Phoshine-induced walking response of the lesser grain borer (Rhyzopertha dominica). Pest Management Science 68, 1368–1373.Google Scholar
Rumbos, C.I., Dutton, A.C. & Athanassiou, C.G. (2013) Comparison of two pirimiphos-methyl formulations against major stored-product insect species. Journal of Stored Products Research 55, 106–115.Google Scholar
Sall, J., Lehman, A. & Creighton, L. (2001) JMP Start Statistics. A Guide to Statistics and Data Analysis using JMP and JMP IN Software. Belmont, CA, Duxbury Press.Google Scholar
Sokal, R.R. & Rohlf, F.J. (1995) Biometry. 3rd edn. New York, W.H. Freeman & Company.Google Scholar
Tomlin, C.D.S. (2000) The Pesticide manual. London, BCPC Publications.Google Scholar
Vassilakos, T.N. & Athanassiou, C.G. (2012 a) Effect of short exposures to spinetoram against three stored-product beetle species. Journal of Economic Entomology 105, 1088–1094.Google Scholar
Vassilakos, T.N. & Athanassiou, C.G. (2012 b) Effect of uneven distribution of spinetoram-treated wheat and rice on mortality and progeny production of Rhyzopertha dominica (F.), Sitophilus oryzae (L.) and Tribolium confusum Jacquelin du Val. Journal of Stored Products Research 50, 73–80.Google Scholar
Vassilakos, T.N. & Athanassiou, C.G. (2013) Effect of temperature and relative humidity on the efficacy of spinetoram for the control of three stored product beetle species. Journal of Stored Products Research 55, 73–77.Google Scholar
Vayias, B.J. & Athanassiou, C.G. (2004) Factors affecting efficacy of the diatomaceous earth formulation SilicoSec against adults and larvae of the confused beetle Tribolium confusum du Val (Coleoptera: Tenebrionidae). Crop Protection 23, 565–573.CrossRefGoogle Scholar
Wijayaratne, L.K.W., Fields, P.G. & Arthur, F.H. (2012) Effect of methoprene on the progeny production of Tribolium castaneum (Coleoptera: Tenebrionidae). Pest Management Science 68, 217–224.CrossRefGoogle ScholarPubMed