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1.
Pestic Biochem Physiol ; 161: 5-11, 2019 Nov.
Artículo en Inglés | MEDLINE | ID: mdl-31685196

RESUMEN

The adulticidal, larvicidal, and repellent activity of 18 trifluoromethylphenyl amides (TFMPAs) was determined against Aedes aegypti mosquitoes. The compounds studied are the third generation designed from active structures of the previous two generations. N-(3,5-Bis(trifluoromethyl)phenyl)-2-chloroacetamide (8f) and N-(3,5-bis(trifluoromethyl)phenyl)-2,2,3,3,3-pentafluoropropanamide (8h) were most active against 1st stage Ae. aegypti larvae with LC50 values of 125 and 2.53 µM; for comparative purposes, the published LC50 for fipronil is 0.014 µM. Compound 8h was the most toxic against adult female Ae. aegypti with an LD50 = 2.12 nmol/mg, followed by 8f, and N-(3,5-bis(trifluoromethyl)phenyl)-2,2,2-trifluoroacetamide (8g) with LD50 values of 4.27 and 4.73 nmol/mg, respectively, although these compounds were significantly less toxic than fipronil against adult female Ae. aegypti. Compounds N-(2-(trifluoromethyl)phenyl)butyramide (9c), N-(2-(trifluoromethyl)phenyl)pentanamide (9d) and N-(2-(trifluoromethyl)phenyl)hex-5-enamide (9e) were the best repellents for female Ae. aegypti, with minimum effective dosages (MEDs) of 0.026, 0.052, and 0.091 µmol/cm2, respectively, compared to DEET at 0.052 µmol/cm2. Out of 52 TFMPAs (total number of compounds from three generations of this research) compound 9c was the most active repellent along with two synthesized in our previous studies, 2-chloro-N-(3-(trifluoromethyl)phenyl)acetamide (6a) and 2,2,2-trifluoro-N-(2-(trifluoromethyl)phenyl)acetamide (4c).


Asunto(s)
Aedes/efectos de los fármacos , Amidas/farmacología , Repelentes de Insectos/farmacología , Insecticidas/farmacología , Aedes/embriología , Animales , Bioensayo , Relación Dosis-Respuesta a Droga , Repelentes de Insectos/administración & dosificación , Repelentes de Insectos/química , Insecticidas/administración & dosificación , Insecticidas/química , Larva/efectos de los fármacos , Relación Estructura-Actividad
2.
Chem Biodivers ; 16(5): e1800618, 2019 May.
Artículo en Inglés | MEDLINE | ID: mdl-30901146

RESUMEN

Trifluoromethylphenyl amides (TFMPAs) were designed and synthesized as potential pesticides. Thirty-three structures were evaluated for fungicidal activity against three Colletotrichum species using direct bioautography assays. Active compounds were subsequently tested against C. fragariae, C. gloeosporioides, C. acutatum, Phomopsis obscurans, P. viticola, Botrytis cinerea and Fusarium oxysporum. The study identified 2-chloro-N-[2,6-dichloro-4-(trifluoromethyl)phenyl]acetamide (7a) as showing the strongest antifungal activity, and the broadest activity spectrum in this set against Colletotrichum acutatum (at 48 and 72 h) and Phomopsis viticola (at 144 h). The presence of triethylamine in its complex with N-[2,6-dichloro-4-(trifluoromethyl)phenyl]-2,2,3,3,3-pentafluoropropanamide (7b') played an important role in the bioactivity, and depending on the concentration or fungal species it showed higher or lower activity than the parent amide. X-Ray crystallography has shown that the complex (7b') is an ion pair, (C10 H2 Cl2 F8 NO)- (C6 H16 N)+ , where a proton is transferred from the amide nitrogen to the triethylamine nitrogen and then connected by hydrogen bonding to the acyl oxygen (N-H 0.893 Å; H⋅⋅⋅O 1.850 Å; N⋅⋅⋅O 2.711 Å; N-H⋅⋅⋅O 161.2(13)°). Although none of these compounds were better than standards, this work revealed some potential lead structures for further development of active novel compounds.


Asunto(s)
Amidas/química , Antifúngicos/química , Amidas/farmacología , Antifúngicos/farmacología , Colletotrichum/efectos de los fármacos , Colletotrichum/crecimiento & desarrollo , Cristalografía por Rayos X , Diseño de Fármacos , Etilaminas/química , Enlace de Hidrógeno , Pruebas de Sensibilidad Microbiana , Conformación Molecular , Plantas/microbiología , Relación Estructura-Actividad
3.
Malar J ; 17(1): 437, 2018 Nov 26.
Artículo en Inglés | MEDLINE | ID: mdl-30477502

RESUMEN

BACKGROUND: The emergence of mosquitoes that can avoid indoor-deployed interventions, such as treated bed nets and indoor residual spraying, threatens the mainstay of malaria control in Zambia. Furthermore, the requirement for high coverage of these tools poses operational challenges. Spatial repellents are being assessed to supplement these vector control tools, but limitations exist in the residual effect of the repellent and the need for external power or heat for diffusion of the volatiles. METHODS: A semi-field evaluation of a novel controlled release spatial repellent device (CRD) was conducted in Macha, Zambia. These devices emanate metofluthrin with no need for external power. Devices were deployed in huts within the semi-field system (SFS). Female Anopheles gambiae sensu stricto released within the SFS were trapped overnight by light traps and collected by aspiration the next morning inside and outside of huts to determine the extent of mosquito repellency and the impact on host-seeking and survival. Experiments studied the impact of number of devices as well as the presence of hut occupants. The study was complemented with numerical methods based on computational fluid dynamics to simulate spatial distribution of metofluthrin. RESULTS: Presence of CRDs was associated with significant reductions in indoor counts of mosquitoes, regardless of whether huts were occupied or not. Repellency ranged from 15 to 60% compared to huts with no devices. Reducing the number of devices from 16 to 4 had little impact on repellency. When huts were occupied, indoor mosquito host-seeking was higher in the presence of CRDs, whilst survival was significantly reduced. CONCLUSIONS: This study demonstrated that deployment of as few as four CRDs within a hut was associated with reduced indoor mosquito densities. As would be expected, presence of occupants within huts, resulted in greater indoor catches (both with and without devices). The increased indoor mosquito host-seeking and mortality in huts when devices were present may be explained by the excito-repellency activity of metofluthrin. These semi-field experiments provide preliminary data on the utility of CRD spatial repellents to reduce indoor densities of An. gambiae mosquitoes. Studies will further investigate the impact of CRDs on mosquito behaviour as well as epidemiological protective efficacy.


Asunto(s)
Anopheles/efectos de los fármacos , Ciclopropanos/farmacología , Transmisión de Enfermedad Infecciosa/prevención & control , Sistemas de Liberación de Medicamentos , Fluorobencenos/farmacología , Fumigación/métodos , Repelentes de Insectos/farmacología , Malaria/prevención & control , Control de Mosquitos/métodos , Animales , Difusión , Conducta Alimentaria , Femenino , Control de Mosquitos/instrumentación , Densidad de Población , Análisis de Supervivencia , Zambia
4.
Pestic Biochem Physiol ; 151: 40-46, 2018 Oct.
Artículo en Inglés | MEDLINE | ID: mdl-30704711

RESUMEN

This project focused on the design, synthesis, and testing of trifluoromethylphenyl amides (TFMPAs) as potential mosquitocides and repellents. Fourteen compounds were evaluated for toxicity against larvae and adults of Aedes aegypti. Several compounds were toxic against Aedes aegypti (larval, adult and feeding bioassays) and Drosophila melanogaster (glass-surface contact assay), but were much less toxic than fipronil, with toxicity ratios ranging from 100-fold in the larval assay to 100,000-fold for topical application to adult insects. In repellency bioassays to determine minimum effective dosage (MED), compound N-(2,6-dichloro-4-(trifluoromethyl)phenyl)-2,2,3,3,3-pentafluoropropanamide (7b) repelled Ae. aegypti females at lower concentration, 0.017 (±0.006) µmol/cm2, than N, N-diethyl-meta-toluamide (DEET) 0.026 (±0.005) µmol/cm2. 2-Chloro-N-(3-(trifluoromethyl)phenyl)acetamide (6a) performed better than DEET against two species of mosquitoes: it repelled Ae. aegypti females at 0.013 (±0.006) µmol/cm2 and Anopheles gambiae females (in a warm body repellent assay), at a standard exposure of 2 nmol/cm2. These studies revealed novel active structures that could further lead to compounds with better repellent activity.


Asunto(s)
Amidas/química , Aedes/efectos de los fármacos , Amidas/síntesis química , Amidas/farmacología , Animales , Anopheles/efectos de los fármacos , DEET/farmacología , Drosophila , Repelentes de Insectos/síntesis química , Repelentes de Insectos/química , Repelentes de Insectos/farmacología , Insecticidas/síntesis química , Insecticidas/química , Insecticidas/farmacología
5.
Saudi Pharm J ; 26(6): 860-864, 2018 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-30202228

RESUMEN

The essential oils (EOs) of Anthemis melampodina (Am) and Anthemis scrobicularis (As) (Asteraceae) were extracted from the aerial parts of the plants by hydrodistillation, and their chemical compositions were analyzed using GC-FID and GC-MS. Fifty-six components representing 85.5% of the oil composition of Anthemis melampdina were identified, and the major components were α-pinene (17.1%) and ß-eudesmol (13.8%). Forty-one components representing 86% of the oil composition of Anthemis scrobicularis were identified, and the major component was ß-eudesmol (12.8%). Laboratory bioassays were conducted to determine repellency of Am and As EOs against the yellow fever mosquito Aedes aegypti L. and the lone star tick Amblyomma americanum L. The minimum effective doses (MEDs) of the Am and As EOs against mosquitoes were 0.187 ±â€¯0.000 and 0.312 ±â€¯0.063 mg/cm2 respectively, which were significantly higher than that of DEET (0.023 ±â€¯0.000 mg/cm2) in human-based repellent bioassays. The As EO was more repellent than Am EO against nymphal ticks but was less effective than DEET in vertical paper bioassays.

6.
Saudi Pharm J ; 25(5): 703-708, 2017 Jul.
Artículo en Inglés | MEDLINE | ID: mdl-28725142

RESUMEN

The essential oil (EO) of the aerial parts of Rhanterium epapposum Oliv. (Asteraceae), was obtained by hydrodistillation. The oil was subsequently analyzed by both GC-FID and GC-MS, simultaneously. Forty-five components representing 99.2% of the oil composition were identified. The most abundant compounds were camphene (38.5%), myrcene (17.5%), limonene (10.1%) and α-pinene (8.7%). Referring to the ethnobotanical utilization, an insecticidal assay was performed, where the oil repelled the yellow fever mosquito Aedes aegypti L. at a minimum effective dose (MED of 0.035 ± 0.010 mg/cm2) compared to the positive control DEET (MED of 0.015 ± 0.004 mg/cm2). Additionally, the in vitro antimicrobial activity against a panel of pathogens was determined using a microdilution method. The acetyl- and butyrylcholine esterase inhibitory activities were measured using the colorimetric Ellman method. The bioassay results showed that the oil was rather moderate in antimicrobial and cholinesterase inhibitions when compared to the standard compounds.

7.
J Med Entomol ; 53(2): 470-2, 2016 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-26637385

RESUMEN

Mosquito-borne pathogens affect millions of people worldwide. This work describes a new method to deliver spatial repellents. Functional microdispensers (FMDs) were designed to deliver spatial repellents against mosquitoes. In vivo trials showed that FMDs protect human subjects against mosquitoes by reducing 70­90% of bites received, with a protection that lasted up to 4 weeks. FMDs can be cost-effectively implemented as wearable or field-dispensed devices for local area protection, defined as a confined geographical region.


Asunto(s)
Repelentes de Insectos/administración & dosificación , Control de Mosquitos , Humanos
8.
J Am Mosq Control Assoc ; 32(4): 282-291, 2016 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-28206863

RESUMEN

Mosquito surveillance in remote areas with limited access to canisters of CO2 or dry ice will benefit from an effective alternative CO2 source, such as the natural production of CO2 from yeast fermentation. In this study, we investigate differences in mosquito capture rates from the Centers for Disease Control and Prevention (CDC) light traps baited with dry ice compared with traps baited with yeast fermentation of several carbohydrate sources over 23 trap-nights. Results demonstrated the ability of yeast-generated CO2 to effectively attract mosquitoes to a CDC trap, regardless of carbohydrate source. Total collections of mosquitoes using dry ice were significantly higher than collections from yeast-generated CO2 sources. However, mosquito community structure, i.e., the species and relative capture rate of each species, was represented comparably across collections regardless of CO2 source. Volatiles produced by yeast fermentation were analyzed by carbohydrate source, revealing a suite of compounds, possibly synergistic, enhancing effects with CO2 on mosquito collection capability compared with the amount of CO2 used to attract mosquitoes.


Asunto(s)
Carbohidratos/análisis , Dióxido de Carbono/metabolismo , Quimiotaxis , Culicidae/fisiología , Control de Mosquitos/métodos , Animales , Fermentación , Florida , Miel/análisis , Melaza/análisis , Saccharomyces cerevisiae/metabolismo , Sacarosa/análisis , Compuestos Orgánicos Volátiles/análisis
9.
J Med Entomol ; 52(1): 93-100, 2015 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-26336285

RESUMEN

The essential oils from the flower, leaf, and stem of Echinophora lamondiana B.Yildiz et Z.Bahcecioglu were analyzed by gas chromatography-flame ionization detection and gas chromatography-mass spectrometry. In total, 41, 37, and 44 compounds were identified, which accounted for 98.0, 99.1, and 97.0% of flower, leaf, and stem essential oils, respectively. The monoterpenic hydrocarbons were found to be high in all samples of the essential oils. The major components of essential oils from flower, leaf, and stem of E. lamondiana were δ-3-carene (61.9, 75.0, and 65.9%, respectively), α-phellandrene (20.3, 14.1, and 12.8%, respectively), and terpinolene (2.7, 3.3, and 2.9%, respectively). Flower and leaf essential oils and terpinolene produced biting deterrence similar to 25 nmol/cm(2) N, N-diethyl-meta-toluamide (DEET; 97%) against Aedes aegypti (L.) and Anopheles quadrimaculatus Say. Compounds (+)-δ-3-carene, (R)-(-)-α-phellandrene, and water-distilled essential oils were significantly less repellent than DEET. Among essential oils, leaf oil was the least toxic of the oils, with an LC50 value of 138.3 ppm, whereas flower essential oil killed only 32% larvae, and no mortality of stem oil at highest tested dosages against Ae aegypti was observed. Terpinolene and α-phellandrene showed higher toxicity than δ-3-carene in both the species. In contrast to Ae. aegypti, all the essential oils showed toxicity in An. quadrimaculatus, and toxicity was higher in leaf oil than the other two oils. These results could be useful in finding new, safe, and more effective natural biopesticides and biting deterrent or repellents against Ae. aegypti.


Asunto(s)
Aedes/efectos de los fármacos , Anopheles/efectos de los fármacos , Apiaceae/química , Mordeduras y Picaduras de Insectos , Repelentes de Insectos/farmacología , Aceites Volátiles/farmacología , Animales , Femenino , Flores/química , Larva/efectos de los fármacos , Aceites Volátiles/química , Hojas de la Planta/química , Tallos de la Planta/química , Especificidad de la Especie
10.
J Am Mosq Control Assoc ; 31(1): 63-70, 2015 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-25843177

RESUMEN

The attraction of female Aedes aegypti to single compounds and binary compositions containing L-lactic acid and an additional saturated compound from a set of ketones, sulfides, and chloroalkanes was studied using a triple-cage dual-port olfactometer. These chemical classes were studied because of their structural relation to acetone, dimethyl disulfide, and dichloromethane, which have all been reported to synergize attraction to L-lactic acid. Human odors, carbon dioxide, and the binary mixture of L-lactic acid and CO2served as controls for comparison of attraction responses produced by the binary mixtures. All tested mixtures that contained chloroalkanes attracted mosquitoes at synergistic levels, as did L-lactic acid and CO2. Synergism was less frequent in mixtures of L-lactic acid with sulfides and ketones; in the case of ketones, synergistic attraction was observed only for L-lactic acid combined with acetone or butanone. Suppression or inhibition of attraction response was observed for combinations that contained ketones of C7-C12 molecular chain length (optimum in the C8-C10 range). This inhibition effect is similar to that observed previously for specific ranges of carboxylic acids, aldehydes, and alcohols.


Asunto(s)
Aedes/efectos de los fármacos , Quimiotaxis/efectos de los fármacos , Ácido Láctico/farmacología , Feromonas/farmacología , Aedes/fisiología , Animales , Femenino , Hidrocarburos Clorados/farmacología , Cetonas/farmacología , Olfatometría , Sulfuros/farmacología
11.
J Med Entomol ; 51(5): 980-8, 2014 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-25276927

RESUMEN

Recently, vector-borne diseases have been resurging in endemic areas and expanding their geographic range into nonendemic areas. Such changes have refocused attention to the potential for major public health events, as naive populations are exposed to these pathogens. Personal topical repellents, recommended by the United States Centers for Disease Control and Prevention and World Health Organization, remain a first line of protection against infection. The current study evaluated the repellent efficacy of four new U.S. Environmental Protection Agency-registered topical repellent products, two with picaridin as the active ingredient and two with IR3535, against a standard DEET (N,N-diethyl-3-methylbenzamide)-based product. All products were evaluated against a wide range of vector species under field conditions across the Americas. Human volunteers were used to evaluate product efficacy as compared with a well-known DEET-based formulation and determine suitability for use by the U.S. military. Findings demonstrated the new formulations performed as well as the standard U.S. military repellent and could be recommended for use.


Asunto(s)
Repelentes de Insectos/farmacología , Piperidinas/farmacología , Propionatos/farmacología , Administración Tópica , Américas , Humanos , Mordeduras y Picaduras de Insectos/prevención & control , Repelentes de Insectos/química
12.
Pest Manag Sci ; 80(2): 586-591, 2024 Feb.
Artículo en Inglés | MEDLINE | ID: mdl-37740933

RESUMEN

BACKGROUND: An important component of the biological activity of pyrethroids, when used in disease vector control, is excito-repellency. In this study, behavioral differences between insecticide susceptible (Orlando) and pyrethroid resistant (Puerto Rican) strains of Aedes aegypti were explored in a round glass arena using fabrics treated with permethrin, etofenprox, deltamethrin, or DDT. Repellency was evaluated across several variables, including the time to first flight (TFF), number of landings (NOL), total flight time (TFT), and maximum surface contact (MSC), all by video analysis. RESULTS: Results from the Orlando strain indicated they were less likely than the Puerto Rican strain to tolerate tarsal contact with the treated fabrics. All four response variables indicated that the mosquito flight and landing behavior was most affected by pyrethroid resistance [knockdown resistance (kdr)] status. In other experiments, mosquitoes were surgically altered, with antennae ablated bilaterally, and these mosquitoes were more likely to stay on the treated surfaces for longer periods of time, irrespective of any chemical exposure. There were also differences in the responses to antennal ablation between the two strains of mosquitoes, indicating that resistance factors, probably kdr, influence the reactivity of mosquitoes to pyrethroid and DDT treatments, and that it was not completely negated by antennal ablation. CONCLUSIONS: These findings confirm the role of antennal olfactory components in the expression of excito-repellent behaviors, and also support the hypothesis that excito-repellency from pyrethroid/DDT exposure is probably due to a combination of sublethal neurotoxic excitation and interactions with the olfactory system. © 2023 Society of Chemical Industry.


Asunto(s)
Aedes , Repelentes de Insectos , Insecticidas , Piretrinas , Animales , Insecticidas/farmacología , Permetrina/farmacología , DDT/farmacología , Resistencia a los Insecticidas , Mosquitos Vectores , Piretrinas/farmacología , Repelentes de Insectos/farmacología
13.
J Med Entomol ; 50(6): 1267-74, 2013 Nov.
Artículo en Inglés | MEDLINE | ID: mdl-24843931

RESUMEN

The essential oil from aerial parts of Ruta chalepensis L. (Sapindales: Rutaceae) was obtained by hydrodistillation, and its chemical profile was identified using gas chromatography and gas chromatography-mass spectrometry. Compounds, 2-undecanone (43.2%), 2-nonanone (27.9%), and 2-nonyl acetate (10.6%) were the major constituents of the oil. Biting deterrent activity of R. chalepensis essential oil at 10 and 50 microg/cm2, 2-undecanone at 8.5 microg/cm2, 2-nonanone at 9 microg/cm2, and 2-nonyl acetate at 9.3 microg/cm2 was similar to DEET (N, N-diethyl-meta-toluamide) at 4.8 microg/cm2, against Aedes aegypti L. Biting deterrent activity of R. chalepensis oil at 50 microg/cm2 against Anopheles quadrimaculatus Say was statistically similar to DEET at 4.8 microg/cm2, whereas the activity was lower in the other compounds tested. In cloth patch assay, R. chalepensis essential oil was effective at 187 microg/cm2, whereas 2-undecanone was effective at 108.9 microg/cm2 against Ae. aegypti. In larval bioassays, 2-undecanone showed similar toxicity whereas toxicity of R. chalepensis essential oil and 2-nonanone was higher at 24-h posttreatment at the LD50 in An. quadrimaculatus than Ae. aegypti. This study revealed that R. chalepensis essential oil and its major compounds were active biting deterrents against Ae. aegypti at higher application rates whereas only the essential oil showed activity similar to DEET against An. quadrimaculatus. 2-undecanone was the most active compound in in vivo repellency bioassay against Ae. aegypti. Chemical composition of R. chalepensis essential oil varies because of plant production and harvest practices, and the activity level of the essential oil may depend on the source of the sample.


Asunto(s)
Aedes/efectos de los fármacos , Anopheles/efectos de los fármacos , Control de Insectos , Repelentes de Insectos/farmacología , Insecticidas/farmacología , Aceites Volátiles/farmacología , Ruta/química , Aedes/crecimiento & desarrollo , Aedes/fisiología , Animales , Anopheles/crecimiento & desarrollo , Anopheles/fisiología , Conducta Alimentaria/efectos de los fármacos , Femenino , Cromatografía de Gases y Espectrometría de Masas , Humanos , Larva/efectos de los fármacos , Larva/crecimiento & desarrollo , Masculino
14.
Pestic Biochem Physiol ; 107(1): 138-47, 2013 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-25149248

RESUMEN

Twenty trifluoromethylphenyl amides were synthesized and evaluated as fungicides and as mosquito toxicants and repellents. Against Aedes aegypti larvae, N-(2,6-dichloro-4-(trifluoromethyl)phenyl)-3,5-dinitrobenzamide (1e) was the most toxic compound (24 h LC50 1940 nM), while against adults N-(2,6-dichloro-4-(trifluoromethyl)phenyl)-2,2,2-trifluoroacetamide (1c) was most active (24 h LD50 19.182 nM, 0.5 µL/insect). However, the 24 h LC50 and LD50 values of fipronil against Ae. aegypti larvae and adults were significantly lower: 13.55 nM and 0.787 × 10(-4) nM, respectively. Compound 1c was also active against Drosophila melanogaster adults with 24 h LC50 values of 5.6 and 4.9 µg/cm(2) for the Oregon-R and 1675 strains, respectively. Fipronil had LC50 values of 0.004 and 0.017 µg/cm(2) against the two strains of D. melanogaster, respectively. In repellency bioassays against female Ae. aegypti, 2,2,2-trifluoro-N-(2-(trifluoromethyl)phenyl)acetamide (4c) had the highest repellent potency with a minimum effective dosage (MED) of 0.039 µmol/cm(2) compared to DEET (MED of 0.091 µmol/cm(2)). Compound N-(2-(trifluoromethyl)phenyl)hexanamide (4a) had an MED of 0.091 µmol/cm(2) which was comparable to DEET. Compound 4c was the most potent fungicide against Phomopsis obscurans. Several trends were discerned between the structural configuration of these molecules and the effect of structural changes on toxicity and repellency. Para- or meta- trifluoromethylphenyl amides with an aromatic ring attached to the carbonyl carbon showed higher toxicity against Ae. aegypti larvae, than ortho- trifluoromethylphenyl amides. Ortho- trifluoromethylphenyl amides with trifluoromethyl or alkyl group attached to the carbonyl carbon produced higher repellent activity against female Ae. aegypti and Anopheles albimanus than meta- or para- trifluoromethylphenyl amides. The presence of 2,6-dichloro- substitution on the phenyl ring of the amide had an influence on larvicidal and repellent activity of para- trifluoromethylphenyl amides.


Asunto(s)
Amidas/toxicidad , Fungicidas Industriales/toxicidad , Repelentes de Insectos/toxicidad , Insecticidas/toxicidad , Aedes/efectos de los fármacos , Amidas/síntesis química , Animales , Drosophila/efectos de los fármacos , Femenino , Hongos/efectos de los fármacos , Hongos/crecimiento & desarrollo , Fungicidas Industriales/síntesis química , Repelentes de Insectos/síntesis química , Insecticidas/síntesis química , Larva/efectos de los fármacos , Dosificación Letal Mediana
15.
Molecules ; 18(4): 4308-27, 2013 Apr 11.
Artículo en Inglés | MEDLINE | ID: mdl-23579997

RESUMEN

The antimicrobial properties of essential oils have been documented, and their use as "biocides" is gaining popularity. The aims of this study were to analyze the chemical composition and assess the biological activities of Hedychium essential oils. Oils from 19 Hedychium species and cultivars were analyzed by gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS) techniques. The antifungal and insecticidal activities of these oils were tested against Colletotrichum acutatum, C. fragariae, and C. gloeosporioides, and three insects, the azalea lace bug (Stephanitis pyrioides), the yellow fever mosquito (Aedes aegypti), and the red imported fire ant (Solenopsis invicta). Hedychium oils were rich in monoterpenes and sesquiterpenes, especially 1,8-cineole (0.1%-42%), linalool (<0.1%-56%), a-pinene (3%-17%), b-pinene (4%-31%), and (E)-nerolidol (0.1%-20%). Hedychium oils had no antifungal effect on C. gloeosporioides, C. fragariae, and C. acutatum, but most Hedychium oils effectively killed azalea lace bugs. The oils also show promise as an adult mosquito repellent, but they would make rather poor larvicides or adulticides for mosquito control. Hedychium oils acted either as a fire ant repellent or attractant, depending on plant genotype and oil concentration.


Asunto(s)
Antifúngicos/química , Insecticidas/química , Aceites Volátiles/química , Zingiberaceae/química , Monoterpenos Acíclicos , Animales , Antifúngicos/farmacología , Bioensayo/métodos , Colletotrichum/efectos de los fármacos , Femenino , Cromatografía de Gases y Espectrometría de Masas , Humanos , Insectos/efectos de los fármacos , Insecticidas/farmacología , Larva/efectos de los fármacos , Masculino , Monoterpenos/química , Monoterpenos/farmacología , Aceites Volátiles/farmacología , Sesquiterpenos/química , Sesquiterpenos/farmacología
16.
J Chem Ecol ; 38(9): 1105-15, 2012 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-22976590

RESUMEN

Insects are the largest and most diverse group of organisms on earth, with over 1,000,000 species identified to date. Stick insects ("walkingsticks" or "phasmids", Order Phasmatodea) are known for and name-derived from their camouflage that acts as a primary line of defense from predation. However, many species also possess a potent chemical defense spray. Recently we discovered that the spray of Asceles glaber contains spiroketals [a confirmed major component: (2S,6R)-(-)(E)-2-methyl-1,7-dioxaspiro[5.5]undecane, and a tentatively identified minor component: 2-ethyl-1,6-dioxaspiro[4.5]decane] and glucose. In this paper, we: 1) illustrate the identification of spiroketals and glucose in the defense spray of A. glaber by using Nuclear Magnetic Resonance (NMR), Gas Chromatography/Mass Spectrometry (GC/MS), and comparison with a synthetic reference sample; 2) provide the elucidation of the absolute configuration of the major spiroketal in that defense spray; and 3) demonstrate the effect of this compound and its enantiomer on both fire ants (Solenopsis invicta) and mosquitoes (Aedes aegypti).


Asunto(s)
Aedes/efectos de los fármacos , Hormigas/efectos de los fármacos , Furanos/metabolismo , Furanos/farmacología , Repelentes de Insectos/metabolismo , Repelentes de Insectos/farmacología , Insectos/metabolismo , Compuestos de Espiro/metabolismo , Compuestos de Espiro/farmacología , Animales , Femenino , Furanos/química , Glucosa/análisis , Glucosa/metabolismo , Glucosa/farmacología , Humanos , Repelentes de Insectos/química , Insectos/fisiología , Masculino , Conducta Predatoria/efectos de los fármacos , Compuestos de Espiro/química , Estereoisomerismo
17.
J Med Entomol ; 49(6): 1370-8, 2012 Nov.
Artículo en Inglés | MEDLINE | ID: mdl-23270165

RESUMEN

In this study we evaluated the biting deterrent effects of a series of saturated and unsaturated fatty acids against Aedes aegypti (L), yellow fever mosquito (Diptera: Culicidae) using the K & Dbioassay module system. Saturated (C6:0 to C16:0 and C18:0) and unsaturated fatty acids (C11:1 to C14:1, C16:1, C18:1, and C18:2) showed biting deterrence index (BDI) values significantly greater than ethanol, the negative control. Among the saturated fatty acids, mid chain length acids (C10:0 to C13:0) showed higher biting deterrence than short (C6:0 to C9:0) and long chain length acids (C14:0 to C18:0), except for C8:0 and C16:0 that were more active than the other short and long chain acids. The BDI values of mid chain length acids (C10:0 to C13:0) were not significantly less than N, N-diethyl-meta-toluamide (DEET), the positive control. Among the unsaturated fatty acids, C11:1 showed the highest activity (BDI = 1.05) and C18:2 had the lowest activity (BDI = 0.7). In C11:1, C12:1, and C14:1 BDI values were not significantly less than DEET. After the preliminary observations, residual activity bioassays were performed on C11:0, C12:0, C11:1, and C12:1 over a 24-h period. All the fatty acids (C11:0, C12:0, C11:1, and C12:1) and DEET showed significantly higher activity at all test intervals than the solvent control. At treatment and 1-h posttreatment, all fatty acids showed proportion not biting (PNB) values not significantly less than DEET. At 3-, 6-, and 12-h posttreatment, all fatty acids showed PNB values significantly greater than DEET. At 24-h posttreatment, only the PNB value for C12:0 was significantly higher than DEET. The dose-responses of C12:0 and DEET were determined at concentrations of 5-25 nmol/cm2. As in the residual activity bioassays, the PNB values for C12:0 and DEET at 25 nmol/cm(2) were not significantly different. However, at lower concentrations, the PNB values for C12:0 were significantly greater than DEET. These results clearly indicate that mid chain length fatty acids not only have levels of biting deterrence similar to DEET at 25 nmnol/cm(2) in our test system, but also appeared to be more persistent than DEET. In contrast, in vivo cloth patch assay system showed that the mid-chain length fatty acids, C11:0, C11:1, C12:0, and C12:1 had minimum effective dose (MED) values greater than DEET against Ae. aegypti and their relative repellency varied according to species tested. The MED values of 120 (C11:0), 145 (C12:0) and 116 (C11:1) nmol/cm(2) against Anopheles quadrimaculatus Say, indicated that these acids were not as potent as DEET with a MED of 54 nmol/cm(2). The MED ratio of the C11:0 and C11:1 for all three mosquito species indicated the C11 saturated and unsaturated acids as more repellent than their corresponding C12:0 and C12:1 homologues.


Asunto(s)
Aedes , Anopheles , Ácidos Grasos Insaturados/química , Mordeduras y Picaduras de Insectos/prevención & control , Repelentes de Insectos/análisis , Adulto , Animales , Femenino , Humanos , Masculino , Relación Estructura-Actividad
18.
J Am Mosq Control Assoc ; 28(2): 123-7, 2012 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-22894125

RESUMEN

Synthetic blends of chemicals identified previously from human skin emanations were evaluated against mosquito and biting fly populations at the Lower Suwannee Wildlife Refuge near Cedar Key, FL. Mosquito Magnet-Experimental traps were baited with the Red (400 ml acetone: 10 ml 1-hexen-3-ol:10 ml 1-octen-3-ol), Blue (400 ml acetone: 1 g/liter lactic acid:20 ml glycolic acid), or Green blend (400 ml acetone:1.5 g/liter lactic acid:20 ml dimethyl disulfide) plus CO2 or with CO2 alone (control). A relative index of efficacy was determined by dividing each mean blend trap catch by the mean control trap catch. Five mosquitoes (Aedes infirmatus, Ae. taeniorhynchus, Ae. triseriatus, Anopheles crucians, and Culex nigripalpus), 2 ceratopogonid (Culicoides floridensis and C. furens), and 1 tabanid (Diachlorus ferrugatus) and phlebotomine (Lutzomyia shannoni) species were trapped. The Red blend + CO2 treatment significantly increased collections of Ae. taeniorhynchus (3.4x), An. crucians (2.8X), total mosquitoes (2.7x), C. furens (17.6x), and L. shannoni (10.8x) compared with control traps. Traps baited with either the Blue or Green blends generally captured fewer insects than traps baited with the other 2 treatments. However, traps baited with the Green blend caught 7 x as many C. furens as the control traps. Responses clearly varied according to species; therefore, "one size does not fit all" when it comes to attractant blends.


Asunto(s)
Dióxido de Carbono , Culicidae , Dípteros , Control de Mosquitos/métodos , Feromonas , Animales , Femenino , Florida , Especificidad de la Especie
19.
Insects ; 13(2)2022 Feb 18.
Artículo en Inglés | MEDLINE | ID: mdl-35206782

RESUMEN

To discover new natural materials for insect management, commercially available stored sheep wool was investigated for attractancy to female adult Aedes aegypti mosquitoes. The volatiles from sheep wool were collected by various techniques of headspace (HS) extractions and hydrodistillation. These extracts were analyzed using gas chromatography-mass spectrometry (GC-MS) and gas chromatography-flame ionization detector (GC-FID) coupled with GC-MS. Fifty-two volatile compounds were detected, many of them known for their mosquito attractant activity. Seven compounds were not previously reported in sheep products. The volatile composition of the extracts varied significantly across collections, depending on the extraction techniques or types of fibers applied. Two types of bioassay were conducted to study attractancy of the sheep wool volatiles to mosquitoes: laboratory bioassays using glass tubes, and semi-field bioassays using large, screened outdoor cages. In bioassays with glass tubes, the sheep wool hydrodistillate and its main component, thialdine, did not show any significant attractant activity against female adult Ae. aegypti mosquitoes. Semi-field bioassays in two large screened outdoor cages, each equipped with a U.S. Centers for Disease Control (CDC) trap and the various bait setups with Vortex apparatus, revealed that vibrating wool improved mosquito catches compared to the setups without wool or with wool but not vibrating. Sheep wool, when vibrated, may release intensively volatile compounds, which could serve as olfactory cues, and play significant role in making the bait attractive to mosquitoes. Sheep wool is a readily available, affordable, and environment-friendly material. It should have the potential to be used as a mosquito management and surveillance component in dynamic bait setups.

20.
Trop Med Infect Dis ; 7(11)2022 Nov 12.
Artículo en Inglés | MEDLINE | ID: mdl-36422923

RESUMEN

U.S. military troops are exposed to mosquito-borne pathogens when deployed to endemic regions. Personal protective measures such as permethrin-treated uniforms and dermal repellents are the cornerstones of mosquito-borne disease prevention for the U.S. military. These measures have limitations and additional personal protection tools, such as spatial repellent devices to decrease the risk of vector-borne pathogen transmission, are required. Novel spatial repellent controlled-release devices formulated with metofluthrin were evaluated in an outdoor setting in the northern Amazon of Peru to evaluate performance under field conditions. The metofluthrin emitting devices lowered the number of mosquitoes captured in protected human landing collections (HLC) compared to blank devices, although there were effect differences between Anopheles spp. and species in other mosquito genera. A computational-experimental model was developed to correlate HLC and active ingredient (AI) concentrations as a function of time and space. Results show a strong correlation between the released AI and the decrease in HLC. This model represents the first effort to obtain a predictive analytical tool on device performance using HLC as the entomological endpoint.

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