Biting Deterrence and Insecticidal Activity of Hydrazide-Hydrazones and Their Corresponding 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazoles Against Aedes aegypti

Abstract

Taking into account the improvement in insecticidal activityby the inclusionof fluorine inthe hydrazone moiety, the authors synthesized new 4-fluorobenzoic acid hydrazides and 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazoles, substituting a phenyl group or a heteroaryl ring carrying one or two atoms of F, Cl and Br, and investigated their biting deterrent and larvicidal activities against Aedes aegypti for the first time. RESULTS:Thecompound3-acetyl-5-(4-fluorophenyl)-2-[4-(dimethylamino)phenyl]-2,3-dihydro-1,3,4-oxadiazole (17)produced the highest biting deterrent activity (BDI = 1.025) against Ae. Aegypti, followed by 4-fluorobenzoic acid [(phenyl)methylene] hydrazide (1). These activity results were similar to those of N,N-diethyl-meta-toluamide (DEET), which showed a proportion not biting of 0.8 0.92. When compounds 1 and 17 were tested on cloth worn on human volunteers, compound 1 was not repellent for some volunteers until present in excess of 500 nmol cm 2, while compound 17 was not repellent at the highest concentration tested (1685 nmol cm 2). In the larvicidal screening bioassays, only compounds 10, 11, 12 and 17 showed 100% mortality at the highest screening dose of 100 ppm against Ae. aegypti larvae. Compounds 11 and 12 with LD50 values of 24.1 and 30.9 ppm showed significantly higher mortality than 10 (80.3 ppm) and 17 (58.7 ppm) at 24-h post-treatment. CONCLUSION: The insecticidal and biting deterrent activities were correlated with the presence of a halogen atom on the phenyl or heteroaryl substituent of the hydrazone moiety.

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Document Details

Document Type
Technical Report
Publication Date
Sep 11, 2012
Accession Number
ADA607154

Entities

People

  • Abbas Ali
  • Bedia Kocyigit-kaymakcioglu
  • Emine E. Oruc-emre
  • Ikhlas A. Khan
  • Nurhayat Tabanca
  • Seda Unsalan
  • Sevim Rollas
  • Ulrich R. Bernier

Organizations

  • University of Mississippi

Tags

Communities of Interest

  • Biomedical

DTIC Thesaurus Topics

  • Anhydrides
  • Assays
  • Bioassay
  • Cells
  • Chemical Industry
  • Chemical Synthesis
  • Chemistry
  • Deterrence
  • Health Services
  • Hydrazides
  • Hydrazines
  • Methylenes
  • Organic Chemistry
  • Oxadiazoles
  • Pest Control
  • Pests
  • Volunteers

Fields of Study

  • Chemistry

Readers

  • Mathematics or Statistics
  • Organic Chemistry
  • Vector-Borne Disease and Entomology