Comparative ecdysteroid action of ring-substituted dibenzoylhydrazines in Spodoptera exigua

Archives of Insect Biochemistry and Physiology

Volumn 41, Issue 1, 1999, Pages 42-53

  Smagghe, Guy ^a   Nakagawa, Yoshiaki ^b   Carton, Bert ^a   Mourad, Ahmed Kamal ^a   Fujita, Toshio ^b   Tirry, Luc ^a  

^a GHENT UNIVERSITY   (Belgium)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

Beet armyworm; Binding; Ecdysone agonist; Evagination; Imaginal disc; Larvicidal toxicity; Methoxyfenozide; Quantitative structure activity relationship; Tebufenozide

Indexed keywords

BETA VULGARIS SUBSP. VULGARIS; CHILO SUPPRESSALIS; INSECTA; LEPIDOPTERA; MYTHIMNA UNIPUNCTA; SPODOPTERA EXIGUA;

EID: 0001827141     PISSN: 07394462     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-6327(1999)41:1<42::AID-ARCH7>3.0.CO;2-H     Document Type: Article

References (40)

1. Bidmon H-J, Sliter TJ. 1990. The ecdysteroid receptor. Invert Reprod Dev 18:13-27.
2. Bondi A. 1964. Van der Waals' volumes and radii. J Phys Chem 68:441-451.
3. c-H cells to ecdysteroids: hormonal specificity. Wilhelm Roux's Arch 189:1-15.
4. Chihara CJ, Petri WH, Fristrom JW, King DS. 1972. The assay of ecdysones and juvenile hormones on Drosophila imaginal discs in vitro. J Insect Physiol 18:1115-1123.
5. De Lean A, Munson PJ, Rodbard D. 1978. Simultaneous analysis of families of sigmoidal curves: application to bioassay, radioligand assay, and physiological dose-response curves. Am J Physiol 235:97-102.
6. Dhadialla TS, Tzertzinis G. 1997. Characterization and partial cloning of ecdysteroid receptor from a cotton boll weevil embryonic cell line. Arch Insect Biochem Physiol 35:45-57.
7. Dhadialla TS, Carlson GR, Le DP. 1998. New insecticides with ecdysteriodal and juvenile hormone activity. Ann Rev Entomol 43:545-569.
8. Hansch C, Fujita T. 1964. ρ-σ-π Analysis. A method for the correlation of biological activity and chemical structure. J Am Chem Soc 86:1616-1626.
9. Heller JJ, Mattioda H, Klein E, Sagenmüller A. 1992. Field evaluation of RH5992 on lepidopterous pests in Europe. Proc Brighton Crop Protect Conf Pests Dis 2:59-65.
10. Henrich VC, Brown NE. 1995. Insect nuclear receptors: a developmental and comparative perspective. Insect Biochem Mol Biol 25:881-897.
11. Hsu AC-T. 1991. 1,2-Diacyl-1-alkylhydrazines. A new class of insect growth regulators. In: Baker DR, Fenyes JG, Moberg WK, editors. Synthesis and chemistry of agrochemicals, II. Washington, DC: American Chemical Society. 443, p 478-490.
12. Jindra J. 1994. Gene regulation by steroid hormones: vertebrates and insects. Eur J Entomol 91:163-187.
13. Le D, Thirugnanam M, Lidert Z, Carlson GR, Bryan JB. 1996. RH-2485: a new selective insecticide for caterpillar control. Proc Brighton Crop Protect Conf Pests Dis 2:481-486.
14. LeOra Software. 1994. User's guide. POLO-PC, probit and logit analysis. Berkeley, CA: LeOra Software. 28 p.
15. Mandaron P. 1976. Ultrastructure des disques de platte de drosophile cultivés in vitro. Evagination, sécrétion de la cuticule nymphale et apolysis. Wilhelm Roux's Archs 179:185-196.
16. Nakagawa Y, Soya Y, Nakai K, Oikawa N, Nishimura K, Ueno T, Fujita T, Kurihara N. 1995. Quantitative structure-activity studies of insect growth regulators. XI. Stimulation and inhibition of N-acetylglucosamine incorporation in a cultured integument system by substituted N-tert-butyl-N,N;prdibenzoylhydrazine . Pestic Sci 43:339-345.
17. Nakagawa Y, Hattori K, Shimizu B, Akamat M, Miyagawa H, Ueno T. 1998. Quantitative structure-activity studies of insect growth regulators. XTV. Three-dimensional quantitative structure-activity relationship of ecdysone agonists including dibenzoylhydrazine analogs. Pestic Sci 53:267-277.
18. Oberlander H. 1985. The imaginal discs. In: Kerkut GA, Gilbert LI, editors. Comprehensive insect physiology biochemistry and pharmacology, vol 2. Oxford: Pergamon Press, p 151-182.
19. Oberlander H, Silhacek DL, Porcheron P. 1995. Non-steroidal ecdysteroid agonists: tools for the study of hormonal action. Arch Insect Biochem Physiol 28:209-223.
20. Oikawa N, Nakagawa Y, Nishimura K, Ueno T, Fujita T. 1994a. Quantitative structure-activity studies of insect growth regulators. X. Substituent effects on larvicidal activity of 1-tert-butyl-1-(2-chlorobenzoyl)-2-(substituted benzoyl) hydrazines against Chilo suppressalis and design synthesis of potent derivates. Pestic Biochem Physiol 48:135-144.
21. Oikawa N, Nakagawa Y, Nishimura K, Ueno T, Fujita T. 1994b. Quantitative structure-activity analysis of larvicidal 1-(substituted benzoyl)-2-benzoyl-1-tert-butylhydrazines against Chilo suppressalis. Pestic Sci 41:139-148.
22. Quack S, Fretz A, Spindler-Barth M, Spindler K. 1995. Receptor affinities and biological responses of nonsteroidal ecdysteroid agonists on the epithelial cell line from Chironomus tentans (Diptera: Chironomidae). Eur J Entomol 92:341-347.
23. Retnakaran A, MacDonald A, Tomkins WL, Davis CN, Brownwright AJ, Palli SR. 1997. Ultrastructural effects of a non-steroidal ecdysone agonist, RH-5992, on the sixth instar larva of the spruce budworm, Choristoneura fumiferana. J Insect Physiol 43:55-68.
24. Shimizu B, Nakagawa Y, Hattori K, Nishimura K, Kurihara N, Ueno T. 1997. Molting hormonal and larvicidal activities of aliphatic acyl analogs of dibenzoylhydrazine insecticides. Steroids 62:638-642.
25. Silhacek DL, Oberlander H, Porcheron P. 1990. Action of RH-5849, a nonsteroidal ecdysone mimic, on Plodia interpunctella (Hübner) in vivo and in vitro. Arch Insect Biochem Physiol 15:201-212.
26. Smagghe G. 1995. Nonsteroidal ecdysteroid agonists: biological activity and insect specificity. PhD dissertation, University of Gent, 118 p.
27. Smagghe G, Degheele D. 1994a. Action of a novel nonsteroidal ecdysteroid mimic, tebufenozide (RH-5992), on insects of different orders. Pestic Sci 42:85-92.
28. Smagghe G, Degheele D. 1994b. Effects of the ecdysteroid agonists RH-5849 and RH-5992, alone and in combination with a juvenile hormone analogue, pyriproxyfen, on larvae of Spodoptera exigua. Entomol Exp Appl 72:115-123.
29. Smagghe G, Degheele D. 1994c. The significance of pharmacokinetics and metabolism to the biological activity of RH-5992 (tebufenozide) in Spodoptera exempta, Spodoptera exigua and Leptinotarsa decemlineata. Pestic Biochem Physiol 49:224-234.
30. Smagghe G, Böhm G-A, Richter K, Degheele D. 1995. Effect of nonsteroidal ecdysteroid agonists on ecdysteroid titer in Spodoptera exigua and Leptinotarsa decemlineata. J Insect Physiol 41:971-974.
31. Smagghe G, Eelen H, Verschelde E, Richter K, Degheele D. 1996a. Differential effects of nonsteroidal ecdysteroid agonists in Coleoptera and Lepidoptera: analysis of evagination and receptor binding in imaginai discs. Insect Biochem Mol Biol 26:687-695.
32. Smagghe G, Viñuela E, Budia F, Degheele D. 1996b. In vivo and in vitro effects on cuticle formation in Spodoptera exigua: an ultrastructural approach. Arch Insect Biochem Physiol 32:121-134.
33. Smagghe G, Carton B, Wesemael W, Ishaaya I, Tirry L. 1998. Ecdysone agonists: mechanism and application on Spodoptera species. Pestic Sci (in press).
34. Steel CGH, Davey KG. 1985. Integration in the insect endocrine system. In: Kerkut GA, Gilbert LI, editors. Comprehensive insect physiology, biochemistry and pharmacology, vol 8. Oxford: Pergamon Press. p 1-35.
35. Terentiou P, Blattman M, Bradbrook D, Käser G, Koolman J. 1993. Biological activity and receptor-binding of ecdysteroids in imaginai discs of Calliphora vicina: a comparison. Insect Biochem Mol Biol 23:131-136.
36. Trisyono A, Chippendale CM. 1997. Effect of the nonsteroidal ecdysone agonists, methoxyfenozide and tebufenozide, on the European corn borer (Lepidoptera: Pyralidae). J Econ Entomol 90:1486-1492.
37. Verloop A. 1983. The STERIMOL approach: further development of the method and the new applications. In: Miyamato J, Kearney PC, editors. Pesticide chemistry, human welfare and environment, vol 1. Oxford: Pergamon Press, p 339-344.
38. Wing KD. 1988. RH-5849, a nonsteroidal ecdysone agonist: effects on a Drosophila cell line. Science 241:467-469.
39. Wing KD, Slawecki R, Carlson GR. 1988. RH-5849, a nonsteroidal ecdysone agonist: effects on larval Lepidoptera. Science 241:470-472.
40. Yund MA, Osterbur DL. 1985. Ecdysteroid receptors and binding proteins. In: Kerkut GA, Gilbert LI, editors. Comprehensive insect physiology, biochemistry, and pharmacology, vol 7. Oxford: Pergamon Press. p 473-490.