Structure-related antifeedant activity of halolactones with a p-menthane system against the lesser mealworm, Alphitobius diaperinus Panzer

Pest Management Science

Volumn 70, Issue 6, 2014, Pages 953-958

  Szczepanik, Maryla ^a   Grudniewska, Aleksandra ^b   Zawitowska, Beata ^a   Wawrzeńczyk, Czeslaw ^b  

^a NICOLAUS COPERNICUS UNIVERSITY   (Poland)

^b WROC AW UNIVERSITY OF ENVIRONMENTAL AND LIFE SCIENCES   (Poland)

Author keywords

Alphitobius diaperinus; Antifeedants; Halolactones; Lesser mealworm; p menthane lactones; Piperitone

Indexed keywords

ADULT; ANTIFEEDANT; BEETLE; HALOGEN; LARVA; RACEMIZATION; SATURATION;

ALPHITOBIUS DIAPERINUS;

INSECTICIDE; LACTONE; PIPERITONE; TERPENE;

ANIMAL; BEETLE; CHEMISTRY; DRUG EFFECTS; LARVA; STRUCTURE ACTIVITY RELATION; TOXICITY;

ANIMALS; BEETLES; INSECTICIDES; LACTONES; LARVA; MONOTERPENES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84899977675     PISSN: 1526498X     EISSN: 15264998     Source Type: Journal    
DOI: 10.1002/ps.3634     Document Type: Article

References (34)

1. Todkar SS, Chavan VV and Kulkarni AS, Screening of secondary metabolites and antibacterial activity of Acacia concinna. Res J Microbiol 5:974-979 (2010).
2. Kalemba D and Kunicka A, Antibacterial and antifungal properties of essential oils. Curr Med Chem 10:813-829 (2003).
3. Regnault-Roger C, The potential of botanical essential oils for insect pest control. Integr Pest Manag Rev 2:25-34 (1997).
4. Isman MB, Botanical insecticides, deterrents, and repellents in modern agriculture and an increasingly regulated world. Annu Rev Entomol 51:45-66 (2006).
5. Szczepanik M, Dams I and Wawrzeńczyk C, Feeding deterrent activity of terpenoid lactones with the p-menthane system against the Colorado potato beetle (Coleoptera: Chrysomelidae). Environ Entomol 34:1433-1440 (2005).
6. Wawrzeńczyk C, Dams I, Szumny A, Szczepanik M, Nawrot J, Pradzyńska A, et al, Synthesis and evaluation of antifeedant, antifungal and antibacterial activity of isoprenoid lactones. Pol J Environ Stud 14(Suppl. II):69-84 (2005).
7. Rodriguez E, Towers GHN and Mitchell JC, Biological activities of sesquiterpene lactones. Phytochemistry 15:1573-1580 (1976).
8. Paruch E, Ciunik Z, Nawrot J and Wawrzenczyk C, Lactones. 9. Synthesis of terpenoid lactones-active insect antifeedants. J Agric Food Chem 48:4973-4977 (2000).
9. Lochyński S, Frackowiak B, Olejniczak T, Ciunik Z and Wawrzeńczyk C, Lactones. Part 15: Synthesis of chiral spirolactones with a carane system-insect feeding deterrents. Tetrahedr Asym 13:1761-1767 (2002).
10. Dancewicz K, Gabryś B, Dams I and Wawrzeńczyk C, Enantiospecific effect of pulegone and pulegone-derived lactones on Myzus persicae (Sulz.) settling and feeding. J Chem Ecol 34:530-538 (2008).
11. Nawrot J, Dams I and Wawrzeńczyk C, Feeding deterrent activity of terpenoid lactones with a p-menthane system against stored-product pests. J Stored Prod Res 45:221-225 (2009).
12. Bowers WS, Ortego F, You X and Evans PH, Insect repellents from the Chinese prickly ash Zanthoxylum bungeanum. J Nat Prod 56:935-938 (1993).
13. Ravid U, Putievsky E and Katzir I, Enantiomeric distribution of piperitone in essential oils of some mentha spp., Calamintha incána (sm.) heldr. and Artemisia judaica L. Flavour Frag J 9:85-87 (1994).
14. Ketoh GK, Koumaglo HK, Glitho IA and Huignard J, Comparative effects of Cymbopogon schoenanthus essential oil and piperitone on Callosobruchus maculatus development. Fitoterapia 77:506-510 (2006).
15. Abdelgaleil SAM, Abbassy MA, Belal A-SH and Abdel Rasoul MAA, Bioactivity of two major constituents isolated from the essential oil of Artemisia judaica L. Bioresour Technol 99:5947-5950 (2008).
16. Marques MMM, Morais SM, Vieira IGP, Vieira MGS, Raquel A, Silva A, et al, Larvicidal activity of Tagetes erecta against Aedes aegypti. J Am Mosq Control Assoc 27:156-158 (2011).
17. Tozlu E, Cakir A, Kordali S, Tozlu G, Ozer H and Aytas Akcin T, Chemical compositions and insecticidal effects of essential oils isolated from Achillea gypsicola, Satureja hortensis, Origanum acutidens and Hypericum scabrum against broadbean weevil (Bruchus dentipes). Sci Hort 130:9-17 (2011).
18. Axtell RC and Arends JJ, Ecology and management of arthropod pests of poultry. Annu Rev Entomol 35:101-126 (1990).
19. Rice SJ and Lambkin TA, A new culture method for lesser mealworm, Alphitobius diaperinus. J Appl Entomol 133:67-72 (2009).
20. Ibrahim MA, Kainulainen P, Aflatuni A, Tiilikkala K and Holopainen JK, Insecticidal, repellent, antimicrobial activity and phytotoxicity of essential oils: with special reference to limonene and its suitability for control of insect pests. Agr Food Sci Finl 10:243-259 (2001).
21. Gabryś B, Dancewicz K, Halarewicz-Pacan A and Janusz E, Effect of natural monoterpenes on the behaviour of the peach potato aphid Myzus persicae (Sulz.). IOBC/WPRS Bull 28:29-34 (2005).
22. Mori K, Semiochemicals-synthesis, stereochemistry, and bioactivity. Eur J Org Chem 1479-1489 (1998).
23. Grudniewska A, Dancewicz K, Bialońska A, Ciunik Z, Gabryś B and Wawrzeńczyk C, Synthesis of piperitone-derived halogenated lactones and their effect on aphid probing, feeding, and settling behavior. RSC Adv 1:498-510 (2011).
24. Wińska K, Grudniewska A, Chojnacka A, Bialońska A and Wawrzeńczyk C, Enzymatic resolution of racemic secondary cyclic allylic alcohols. Tetrahedr Asym 21:670-678 (2010).
25. Grudniewska A, Dancewicz K, Bialońska A, Wawrzeńczyk C and Gabryś B, Piperitone-derived saturated lactones: synthesis and aphid behaviour-modifying activity. J Agric Food Chem 61:3364-3372 (2013).
26. Szczepanik M, Dams I and Wawrzeńczyk C, Terpenoid lactones with the p-menthane system as feeding deterrents to the lesser mealworm, Alphitobius diaperinus. Entomol Exp Appl 128:337-345 (2008).
27. Nawrot J, Bloszyk E, Harmatha J, Novotny L and Drozdz B, Action of antifeedants of plant origin on beetles infesting stored products. Acta Entomol Bohemos 83:327-335 (1986).
28. Koul O, Bioassays, in Insect Antifeedants. CRC Press, London/New York/Washington, pp. 25-42 (2004).
29. Hammer Ř, Harper DAT and Ryan PD, PAST: Paleontological Statistics Software Package for Education and Data Analysis. [Online]. Palaeontologia Electronica 4 (2001). Available: http://palaeo-electronica.org/2001_1/past/issue1_01.htm [3 March 2013].
30. López-Olguín J, de la Torre MC, Ortego F, Castañera P and Rodríguez B, Structure-activity relationships of natural and synthetic neo-clerodane diterpenes from Teucrium against Colorado potato beetle larvae. Phytochemistry 50:749-753 (1999).
31. Argandoña VH, Rovirosa J, San-Martín A, Riqueleme A, Díaz-Marrero AR, Cueto M, et al, Antifeedant effects of marine halogenated monoterpenes. J Agric Food Chem 50:7029-7033 (2002).
32. Samarasekera R, Weerasinghe IS and Hemalal KDP, Insecticidal activity of menthol derivatives against mosquitoes. Pest Manag Sci 64:290-295 (2008).
33. Grotowska AK and Wawrzeńczyk C, Lactones 13: Biotransformation of iodolactones. Mol Catal B Enzym 19-20:203-208 (2002).
34. Grabarczyk M, Fungal strains as catalysts for the biotransformation of halolactones by hydrolytic dehalogenation with the dimethylcyclohexane system. Molecules 17:9741-9753 (2012).