COMPARATIVE ECDYSTEROID ACTION OF RING-SUBSTITUTED DIBENZOYLHYDRAZINES IN SPODOPTERA EXIGUA

doi:10.1002/(SICI)1520-6327(1999)41:1<42::AID-ARCH7>3.0.CO;2-H

Paper

COMPARATIVE ECDYSTEROID ACTION OF RING-SUBSTITUTED DIBENZOYLHYDRAZINES IN SPODOPTERA EXIGUA

Published 1999 · G. Smagghe, Y. Nakagawa, B. Carton

Archives of Insect Biochemistry and Physiology

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Abstract

Ring-substituted dibenzoylhydrazines are well known as nonsteroidal ecdysone agonists that cause precocious larval molt leading to death. Among them, tebufenozide (RH-5992) is used in practice as insecticide to control lepidopteran pests selectively. Recently, a new dibenzoylhydrazine, methoxyfenozide (RH-2485), with a higher activity for Lepidoptera, has been discovered. To obtain insight into the molecular mechanisms involved in the insecticidal selectivity of the dibenzoylhydrazine family, we measured the in vivo toxicity of these dibenzoylhydrazines against larval stages of the beet armyworm, Spodoptera exigua, and their action on in vitro cultured imaginal discs. We found that both nonsteroidal ecdysone agonists induced premature and lethal molting, and caused the same effect as 20-hydroxyecdysone in vitro. Furthermore, we measured the larvicidal activity against S. exigua of a series of dibenzoylhydrazines, in which ring-substituents were varied in a range of halogen, lower alkyl, OCH3, SCH3, Ph, CN, NO2, and CF3. The substituent effects on the larvicidal activity against S. exigua were very similar to that for another lepidopteran insect species Chilo suppressalis, suggesting that the molecular mechanism of action of these compounds is similar within both lepidopteran species. Arch. Insect Biochem. Physiol. 41:42–53, 1999. © 1999 Wiley-Liss, Inc.

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Ring-substituted dibenzoylhydrazines cause premature and lethal molting in larval stages of the beet armyworm, Spodoptera exigua, suggesting similar molecular mechanisms of action within both lepidopteran species.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

COMPARATIVE ECDYSTEROID ACTION OF RING-SUBSTITUTED DIBENZOYLHYDRAZINES IN SPODOPTERA EXIGUA

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References

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The benzoyl moiety near the tert-butyl group is crucial for maintaining high activity in ecdysone agonists, which cause premature molting in insect larvae.

Effect of the Nonsteroidal Ecdysone Agonists, Methoxyfenozide and Tebufenozide, on the European Corn Borer (Lepidoptera: Pyralidae)

Methoxyfenozide and tebufenozide show potential as insect growth regulators for controlling the European corn borer, Ostrinia nubilalis, by inducing premature molting cycles and inhibiting larval growth.

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The benzoyl moiety of dibenzoylhydrazines can be replaced by aliphatic acyl groups without significantly affecting their biological activities.

Ultrastructural Effects of a Non-Steroidal Ecdysone Agonist, RH-5992, on the Sixth Instar Larva of the Spruce Budworm, Choristoneura fumiferana.

RH-5992 causes premature, incomplete moulting in sixth instar spruce budworm larvae, leading to moribund death due to starvation and desiccation.

Differential effects of nonsteroidal ecdysteroid agonists in coleoptera and lepidoptera: Analysis of evagination and receptor binding in imaginal discs

Nonsteroidal ecdysteroid agonists show similar effects to 20E, but their specific activity and insect selectivity are related to their selective binding on ecdysteroid receptors in imaginal discs of insect larvae.

Citations

Structure-activity relationship of imidazothiadiazole analogs for the binding to the ecdysone receptor of insect cells.

Imidazothiadiazole analogs show strong binding to the ecdysone receptor in lepidopteran cells, but low or not observed in dipteran and coleopteran cells.

Determination of 16 insect growth regulators in edible Chinese traditional herbs by liquid chromatography electrospray tandem mass spectrometry

The developed LC-MS/MS method effectively detects and quantifies 16 insect growth regulator residues in Chinese traditional herbs, with excellent linearity and precision.

Determination of Methoxyfenozide Residues in Water and Soil by Liquid Chromatography: Evaluation of its Environmental Fate Under Laboratory Conditions

Methoxyfenozide dissipates rapidly and does not accumulate in water, as demonstrated by a simple, effective, and sensitive method for analyzing its presence in water and soil under laboratory conditions.

Multidimensional Quantitative Structure–Activity Relationships of Diacylhydrazine Toxicity to Lepidopteran and Coleopteran Insect Pests

Diacylhydrazines show potential as effective insecticides against Lepidopteran and Coleopteran pests, with structure-activity relationships partially rationalized by Ecdysone Receptor sequence alignments.

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Chromone and chromone analogues of diacylhydrazines show promising insecticidal activity against Mythima separata, suggesting their potential as environmentally benign insecticides.