Evaluation of DIMBOA analogs as antifeedants and antibiotics towards the aphid Sitobion avenae in artificial diets

Carlos A. Escobar, Dieter Sicker, Hermann M. Niemeyer

Resultado de la investigación: Article

25 Citas (Scopus)

Resumen

A total of 25 compounds including benzoxazinones, benzoxazolinones, and N-glyoxylamide derivatives were tested as antifeedants and antibiotics towards the aphid Sitobion avenae in diet bioassays. The antifeedant and mortality indexes increased with the presence of electron-donating groups in the 7 position of the benzoxazinone moiety, the replacement of the oxygen atom by sulfur in the heterocyclic ring, the presence of a hemiacetal instead of an acetal at C-2 of the benzoxazine moiety (and hence the possibility of ring opening), and the presence of a hydroxyl group at C-4 of the benzoxazine moiety (hydroxamic acid) instead of a hydrogen atom (lactam). The results support earlier hypotheses on the chemical bases for the mode of action of these compounds.

Idioma originalEnglish
Páginas (desde-hasta)1543-1554
Número de páginas12
PublicaciónJournal of Chemical Ecology
Volumen25
N.º7
DOI
EstadoPublished - 1 ene 1999

Huella dactilar

Benzoxazines
benzoxazinoids
antifeedant
Sitobion avenae
Aphids
artificial diet
antifeedants
artificial diets
Nutrition
aphid
antibiotics
Aphidoidea
lactams
hydroxamic acids
Anti-Bacterial Agents
Diet
hydrogen
bioassay
mechanism of action
sulfur

ASJC Scopus subject areas

  • Ecology, Evolution, Behavior and Systematics
  • Biochemistry

Citar esto

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abstract = "A total of 25 compounds including benzoxazinones, benzoxazolinones, and N-glyoxylamide derivatives were tested as antifeedants and antibiotics towards the aphid Sitobion avenae in diet bioassays. The antifeedant and mortality indexes increased with the presence of electron-donating groups in the 7 position of the benzoxazinone moiety, the replacement of the oxygen atom by sulfur in the heterocyclic ring, the presence of a hemiacetal instead of an acetal at C-2 of the benzoxazine moiety (and hence the possibility of ring opening), and the presence of a hydroxyl group at C-4 of the benzoxazine moiety (hydroxamic acid) instead of a hydrogen atom (lactam). The results support earlier hypotheses on the chemical bases for the mode of action of these compounds.",
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Evaluation of DIMBOA analogs as antifeedants and antibiotics towards the aphid Sitobion avenae in artificial diets. / Escobar, Carlos A.; Sicker, Dieter; Niemeyer, Hermann M.

En: Journal of Chemical Ecology, Vol. 25, N.º 7, 01.01.1999, p. 1543-1554.

Resultado de la investigación: Article

TY - JOUR

T1 - Evaluation of DIMBOA analogs as antifeedants and antibiotics towards the aphid Sitobion avenae in artificial diets

AU - Escobar, Carlos A.

AU - Sicker, Dieter

AU - Niemeyer, Hermann M.

PY - 1999/1/1

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N2 - A total of 25 compounds including benzoxazinones, benzoxazolinones, and N-glyoxylamide derivatives were tested as antifeedants and antibiotics towards the aphid Sitobion avenae in diet bioassays. The antifeedant and mortality indexes increased with the presence of electron-donating groups in the 7 position of the benzoxazinone moiety, the replacement of the oxygen atom by sulfur in the heterocyclic ring, the presence of a hemiacetal instead of an acetal at C-2 of the benzoxazine moiety (and hence the possibility of ring opening), and the presence of a hydroxyl group at C-4 of the benzoxazine moiety (hydroxamic acid) instead of a hydrogen atom (lactam). The results support earlier hypotheses on the chemical bases for the mode of action of these compounds.

AB - A total of 25 compounds including benzoxazinones, benzoxazolinones, and N-glyoxylamide derivatives were tested as antifeedants and antibiotics towards the aphid Sitobion avenae in diet bioassays. The antifeedant and mortality indexes increased with the presence of electron-donating groups in the 7 position of the benzoxazinone moiety, the replacement of the oxygen atom by sulfur in the heterocyclic ring, the presence of a hemiacetal instead of an acetal at C-2 of the benzoxazine moiety (and hence the possibility of ring opening), and the presence of a hydroxyl group at C-4 of the benzoxazine moiety (hydroxamic acid) instead of a hydrogen atom (lactam). The results support earlier hypotheses on the chemical bases for the mode of action of these compounds.

KW - Antibiotics

KW - Aphids

KW - DIMBOA

KW - Feeding deterrents

KW - Sitobion avenue

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DO - 10.1023/A:1020832731546

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JO - Journal of Chemical Ecology

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