Evaluation of (-)-borneol derivatives against the Zika vector, Aedes aegypti and a non-target species, Artemia sp.

Zika, dengue, and chikungunya are vector-borne diseases of pronounced concern transmitted by the mosquito Aedes aegypti Linn. (Diptera: Culicidae). The most important method to avoid outbreaks is to control mosquito spreading by the employment of insecticides and larvicides. Failure to control mosquito dispersal is mostly accounted to Ae. aegypti resistance to currently available larvicides and insecticides, encouraging the development of novel pesticides. In addition, the excessive use of larvicides poses serious threats to human health and the environment. Evaluation of natural products as larvicides in an attempt to overcome this situation is often found in the literature because products originated from nature are considered less toxic to non-target species and more eco-friendly. (-)-Borneol is a bicyclic monoterpene present in essential oils with moderate larvicidal activity. On account of these facts, it was of our interest to synthesize (-)-borneol ester derivatives aiming to study its structure-activity relationships against Ae. aegypti larvae. With the goal to estimate toxicity to a non-target species, evaluation of the lethal concentration 50% (LC50) on Artemia sp. (Artemiidae) and calculation of selectivity towards Ae. aegypti were carried out. The most potent derivative, (-)-Bornyl chloroacetate, exhibited the highest suitability index, demonstrating lower environmental toxicity than other borneol ester derivatives. A parabolic relationship between (-)-borneol esters larvicidal activity and partition coefficient (Log P) was achieved and a correlation equation obtained, validating the importance of lipophilicity to the larvicidal activity of these compounds.

Synthesis, activity, and QSAR studies of tryptamine derivatives on third-instar larvae of Aedes aegypti Linn.

Special attention has been given to the mosquito Aedes aegypti Linn. (Diptera: Culicidae) owing to numerous dengue epidemic outbreaks worldwide. Failure to control vector spreading is accounted for unorganized urban growth and resistance to larvicides and insecticides. Therefore, researchers are currently searching for new and more efficient larvicides and insecticides to aid dengue control measures. Triptamine is known to affect insect behavior, development, and physiology. Expression of this compound in plants has reduced the growth rate of herbivore insects. In view of these facts, it was of our interest to synthesize triptamine amide derivatives as potential larvicides against Ae. aegypti, establishing a Structure-Activity Relationship. Eleven amide derivatives of triptamine were synthesized, characterized, and evaluated for their larvicidal activity against third-instar Ae. aegypti larvae. N-(2-(1H-indol-3-yl)ethyl)-2,2,2-trichloroacetamide exhibited the highest overall larvicidal potency, while N-(2-(1H-Indol-3-yl)ethyl) acetamide displayed the lowest larvicidal potency. A regression equation correlating the larvicidal activity with Log P was obtained. We have found a clear relationship between the larvicidal activity of non-chlorinated compounds and Log P. Analysis of the relationship between Log P and larvicidal activity against Ae. aegypti may be useful in the evaluation of potential larvicidal compounds.

Structure-activity relationships of eugenol derivatives against Aedes aegypti (Diptera: Culicidae) larvae.

BACKGROUND: Dengue fever is a severe public health problem for several countries. In order to find effective larvicides to aid control programs, the structure-activity relationships of eugenol derivatives against Aedes aegypti (Diptera: Culicidae) larvae were evaluated. Additionally, the composition and larvicidal activity of Syzygium aromaticum essential oil was assessed. RESULTS: Four compounds representing 99.05% of S. aromaticum essential oil have been identified. The essential oil was active against Ae. aegypti larvae (LC(50) = 62.3 and 77.0 ppm, field-collected and Rockefeller larvae respectively). The larvicidal activity of eugenol, the major compound of the essential oil, was further evaluated (LC(50) = 93.3 and 71.9 ppm, field-collected and Rockefeller larvae respectively). The larvicidal activity and structure-activity relationships of synthetic derivatives of eugenol were also assessed. The larvicidal activity of the derivatives varied between 62.3 and 1614.9 ppm. Oxidation of eugenol allylic bond to a primary alcohol and removal of the phenolic proton resulted in decreased potency. However, oxidation of the same double bond in 1-benzoate-2-methoxy-4-(2-propen-1-yl)-phenol resulted in increased potency. CONCLUSION: Structural characteristics were identified that may contribute to the understanding of the larvicidal activity of phenylpropanoids. The present approach may help future work in the search for larvicidal compounds.

Structure-activity relationships of larvicidal monoterpenes and derivatives against Aedes aegypti Linn.

In the search for larvicidal compounds against Aedes aegypti L. (Diptera: Culicidae), a collection of monoterpenes were selected and evaluated. R- and S-limonene exhibited the highest larvicidal potency (LC(50)=27 and 30 ppm, respectively), followed by γ-terpinene (LC(50)=56 ppm) and RS-carvone (LC(50)=118 ppm). Structural characteristics which may contribute to the understanding of the larvicidal activity of monoterpenes were empirically identified. The presence of heteroatoms in the basic hydrocarbon structure decreases larvicidal potency. Conjugated and exo double bonds appear to increase larvicidal potency. Replacement of double bonds by more reactive epoxides decreases the larvicidal potency. The presence of hydroxyls in the cyclic structure resulted in decreased potency, probably due to increased polarity indicanting that lipophilicity seems to play an important role in increasing the larvicidal potency in this set of compounds.

Toxic effects on and structure-toxicity relationships of phenylpropanoids, terpenes, and related compounds in Aedes aegypti larvae.

In the search for toxic compounds against Aedes aegypti L. (Diptera: Culicidae) larvae, a collection of commercially available aromatic and aliphatic diversely substituted compounds were selected and evaluated. p-Cymene exhibited the highest larvicidal potency LC50 = 51 ppm, whereas 1,8-cineole exhibited the lowest activity value LC50 = 1419 ppm. To aid future work on the search for larvicidal compounds, the structure-toxicity relationships of this collection have been evaluated. The presence of lipophilic groups results in an overall increase in potency. In general, the presence of hydroxyl groups resulted in less potent compounds. However, methylation of such hydroxyls led to an overall increase in potency. The most potent compounds showed comparably good larvicidal activity in A. aegypti larvae as other terpenes, which we assume to be the result of the increased lipophilicity.

[Periodicity of capture of the Anopheles darlingi Root (Diptera: Culicidae) in Porto Velho, Rondônia, Brazil]. / Periodicidade de captura de Anopheles darlingi Root (Diptera: Culicidae) em Porto Velho, RO.

Anopheles darlingi Root is the principal malaria vector in Amazonia region. The objectives of this work were to study the periodicity of Anopheles darlingi Root, the host preference for peri or extra-domestic environments and the parous rate in four field sites in Porto Velho (RO) by human-landing. All of the Anopheles specimens collected were identified, but only A. darlingi was dissected for the parous study. The results showed that human-landing colleted a total of 985 anophelines, with A. darlingi (972) being the most abundant species. Female mosquitoes were more abundant at extra-domestic environments in two of the locations studied (São João e Candeias do Jamari) (P < 0.05). The parous rate was 96% and no periodicity was observed for captures of females of A. darlingi in the field sites.

Periodicidade de captura de Anopheles darlingi Root (Diptera: Culicidae) em Porto Velho, RO / Periodicity of capture of the Anopheles darlingi Root (Diptera: Culicidae) in Porto Velho, Rondônia, Brazil

Anopheles darlingi Root é o principal vetor de malária na Amazônia brasileira. Os objetivos deste trabalho foram avaliar a periodicidade de captura, a preferência por peri ou extradomicílio e a taxa de paridade de A. darlingi em quatro localidades em Porto Velho, RO, utilizando a atração humana. Todos os anofelinos capturados foram identificados e A. darlingi foi dissecada para caracterização da paridade. Do total de 985 anofelinos coletados, 972 eram A. darlingi. O número de fêmeas foi significativamente maior no extradomicílio em duas das localidades estudadas (São João e Candeias do Jamari) (P < 0,05). A taxa de paridade foi de 96 por cento e não foi observado horário preferencial para captura de fêmeas de A. darlingi nas localidades estudadas.

Anopheles darlingi Root is the principal malaria vector in Amazonia region. The objectives of this work were to study the periodicity of Anopheles darlingi Root, the host preference for peri or extra-domestic environments and the parous rate in four field sites in Porto Velho (RO) by human-landing. All of the Anopheles specimens collected were identified, but only A. darlingi was dissected for the parous study. The results showed that human-landing colleted a total of 985 anophelines, with A. darlingi (972) being the most abundant species. Female mosquitoes were more abundant at extra-domestic environments in two of the locations studied (São João e Candeias do Jamari) (P < 0.05). The parous rate was 96 percent and no periodicity was observed for captures of females of A. darlingi in the field sites.