2020
DOI: 10.3390/ijms21239257
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New Eugenol Derivatives with Enhanced Insecticidal Activity

Abstract: Eugenol, the generic name of 4-allyl-2-methoxyphenol, is the major component of clove essential oil, and has demonstrated relevant biological potential with well-known antimicrobial and antioxidant actions. New O-alkylated eugenol derivatives, bearing a propyl chain with terminals like hydrogen, hydroxyl, ester, chlorine, and carboxylic acid, were synthesized in the present work. These compounds were later subjected to epoxidation conditions to give the corresponding oxiranes. All derivatives were evaluated ag… Show more

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Cited by 37 publications
(35 citation statements)
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References 38 publications
(43 reference statements)
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“…In their studies, Fernandez et al [ 46 ] investigated the efficacy of semisynthetic eugenol derivatives—such as O -alkylated bearing the propyl chain with hydrogen, hydroxyl, ester, chlorine, and carboxylic acid as terminals and corresponding O -alkylated oxiranes against the Sf9 ( Spodoptera frugiperda ) insect cell line. The insecticide activity of eugenol derivatives was also compared to a commercial synthetic insecticide, chlorpyrifos.…”
Section: Eugenol Derivativesmentioning
confidence: 99%
“…In their studies, Fernandez et al [ 46 ] investigated the efficacy of semisynthetic eugenol derivatives—such as O -alkylated bearing the propyl chain with hydrogen, hydroxyl, ester, chlorine, and carboxylic acid as terminals and corresponding O -alkylated oxiranes against the Sf9 ( Spodoptera frugiperda ) insect cell line. The insecticide activity of eugenol derivatives was also compared to a commercial synthetic insecticide, chlorpyrifos.…”
Section: Eugenol Derivativesmentioning
confidence: 99%
“…It is used in perfumeries for its pleasant fragrance, as a flavoring agent in foods, as antiseptic and disinfectant in dental products and in many other fields [ 169 ]. Eugenol can be readily functionalized through the chemical transformation of the phenolic -OH group (mainly via the classical etherification and esterification reactions) [ 170 , 171 , 172 , 173 , 174 , 175 , 176 ], on the aromatic ring (through nitration reaction or Mannich bases formation) [ 177 , 178 , 179 , 180 ], as well as on the allylic functionality, through epoxidation [ 175 ] ( Figure 2 ).…”
Section: Monophenolsmentioning
confidence: 99%
“…For the assessment of viability, a resazurin-based method was used, as previously described [51]. Sf9 cells were plated at a density of 3 × 10 4 cells/well, incubated for 24 h and then exposed to the molecules under study for 24 h. After this period, a commercial solution of resazurin was added (1:10) and the kinetic reaction of fluorescence increase was monitored.…”
Section: Assessment Of Viabilitymentioning
confidence: 99%