Potential of some monoterpenoids and their new N-methyl carbamate derivatives against Schistosomiasis snail vector, Biomphalaria alexandrina

Radwan, Mohamed; El-Zemity, Saad R.; Mohamed, Sahar; Sherby, Shebl M.

doi:10.1016/j.ecoenv.2007.07.002

Cited by 21 publications

(16 citation statements)

References 17 publications

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“…However, from an ecotoxicological point of view, this chemical is highly toxic against non-target soft-bodied aquatic organisms and leads to marked decline of them in several areas (da Silva et al 2013, but see Andrews et al 1982 for non-toxic effects on humans). To overcome this challenge, some eco-friendly tools have been developed, including the use of plant-borne compounds as molluscicides to control freshwater snails (Chifundera et al 1993;Brackenbury 1999;Lahlou 2003;Radwan et al 2008;Jaiswal and Singh 2009;Kumar et al 2010;Rapado et al 2011;da Silva et al 2013;Teixeira et al 2012;Singh et al 2010).…”

Section: Introductionmentioning

confidence: 99%

Mediterranean essential oils as effective weapons against the West Nile vector Culex pipiens and the Echinostoma intermediate host Physella acuta: what happens around? An acute toxicity survey on non-target mayflies

et al. 2015

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Mosquitoes (Diptera: Culicidae) represent a threat for millions of people worldwide, since they act as vectors for important pathogens, including malaria, yellow fever, dengue and West Nile. Second to malaria as the world's most widespread parasitic disease, infection by trematodes is a devastating public health problem. In this study, we proposed two essential oils from plants cultivated in Mediterranean regions as effective chemicals against mosquitoes and freshwater snails vectors of Echinostoma trematodes. Chemical composition of essential oils from Achillea millefolium (Asteraceae) and Haplophyllum tuberculatum (Rutaceae) was investigated. Acute toxicity was evaluated against larvae of the West Nile vector Culex pipiens (Diptera: Culicidae) and the invasive freshwater snail Physella acuta (Mollusca: Physidae), an important intermediate host of many parasites, including Echinostoma revolutum (Echinostomidae). Acute toxicity of essential oils was assessed also on a non-target aquatic organism, the mayfly Cloeon dipterum (Ephemeroptera: Baetidae). Achillea millefolium and H. tuberculatum essentials oils were mainly composed by oxygenated monoterpenes (59.3 and 71.0 % of the whole oil, respectively). Chrysanthenone and borneol were the two major constituents of Achillea millefolium essential oil (24.1 and 14.2 %, respectively). Major compounds of H. tuberculatum essential oil were cis-p-menth-2-en-1-ol and trans-p-menth-2-en-1-ol (22.9 and 16.1 %, respectively). In acute toxicity assays, C. pipiens LC50 was 154.190 and 175.268 ppm for Achillea millefolium and H. tuberculatum, respectively. P. acuta LC50 was 112.911 and 73.695 ppm for Achillea millefolium and H. tuberculatum, respectively, while the same values were 198.116 and 280.265 ppm for C. dipterum. Relative median potency analysis showed that both tested essential oils were more toxic to P. acuta over C. dipterum. This research adds knowledge on plant-borne chemicals toxic against invertebrates of medical importance, allowing us to propose the tested oils as effective candidates to develop newer and safer vector control tools.

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Section: Introductionmentioning

confidence: 99%

Mediterranean essential oils as effective weapons against the West Nile vector Culex pipiens and the Echinostoma intermediate host Physella acuta: what happens around? An acute toxicity survey on non-target mayflies

et al. 2015

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“…Plant extracts have been used to control the snail population with the advantage that, besides being less toxic in nature, they can be degraded faster than the synthetic molluscicides that have also high cost, possible build up of snail resistance, and toxicity in nontarget organisms (Jaiswal and Singh, 2008;Radwan et al, 2008). Many plant products have been found to have a high molluscicidal potential (Singh et al, 1996aLahlou and Berrada, 2001; Singh and Singh, 2005;Silva et al, 2006;Adenusi and Odaibo, 2008;El-Kamali et al, 2010;Kumar et al, 2010;Larhsini et al, 2010;Upadhyay and Singh, 2011).…”

Section: Introductionmentioning

confidence: 99%

Assessment of molluscicidal activity of essential oils from five Azorean plants against Radix peregra (Müller, 1774)

et al. 2012

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a b s t r a c tThe molluscicidal activity of essential oils from two endemic (Juniperus brevifolia; Laurus azorica) and three introduced (Hedychium gardnerianum; Pittosporum undulatum; Psidium cattleianum) Azorean plants against the snail Radix peregra was studied under laboratory conditions. Essential oils from leaves of H. gardnerianum, L. azorica and J. brevifolia presented promising molluscicidal activity on both adults and juveniles stages of R. peregra. The molluscicidal activity of these essential oils was found to be both time and concentration dependent. Lethal concentrations (LC 50 ) varied between 15.4 (L. azorica) and 44.6 ppm (H. gardnerianum) for juveniles and from 45.3 (H. gardnerianum) to 54.6 ppm (J. brevifolia) for R. peregra adults. Ovicidal effect, calculated as percentage of egg hatching, at 100 ppm concentration, was observed in essential oils from P. undulatum flowers (4.2% of hatching) and leaves of H. gardnerianum (4.9%), L. azorica (7.4%) and J. brevifolia (17.7%). The present study is the first attempt to assess the molluscicidal potential of some Azorean plants essential oils against a Lymnaeidae snail. In fact, the H. gardnerianum, L. azorica and J. brevifolia can offer natural alternative tools for the control of R. peregra population, but more research is needed in order to determine the mode of action of these oils and determine the side effects on the ecosystem where this freshwater snail occurs.

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“…We should highlight that literature described that long period of time (ca. 1 week) were required to complete this reaction at room temperature [22].…”

Section: Synthesis Of the Carbonate B-citronellylmentioning

confidence: 99%

“…El-Zemity et al have synthesized terpinyl carbamates through reaction of isocyanate and terpenic alcohols in the presence of a catalytic amount of triethylamine [22]. However, despite 70 % yielding, it was necessary 1 week to complete the reaction at room temperature.…”

Section: General Aspectsmentioning

confidence: 99%

Tin-Catalyzed Urea Alcoholysis With β-Citronellol: A Simple and Selective Synthesis of Carbamates

Chaves

Silva

2016

Catal Lett

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Tin(II) chloride is a stable and water tolerant Lewis acid, commercially available and less corrosive than Brønsted acid catalysts. Our proposal was demonstrated that SnCl 2 was an efficient catalyst on the urea alcoholysis with b-citronellol. We investigated the effects of main reaction parameters such as concentration and tin(II) catalyst nature, reagents stoichiometry and reaction temperature. In homogenous conditions with DMSO as solvent, the SnCl 2 -catalyzed urea alcoholysis reactions under air flux achieved high conversion and selectivity for b-citronellyl carbamate (ca. 90 and 95 %, respectively). Among tin(II) catalysts assessed, SnCl 2 was more active due to its total solubility. Possible intermediates of active Sn(II) species were discussed based on the results of catalytic runs and FT-IR spectroscopy measurements of the liquid phase after the reaction. FT-IR spectroscopy data showed that the active species could be a complex of a Sn(II) atom coordinated with N=C=O. This novel and phosgene-free selective process provide an inexpensive and attractive route to synthesize terpenic carbamates through inexpensive and renewable reactant (i.e. urea). Moreover, SnCl 2 was also an efficient catalyst on synthesis of b-citronellyl carbonate. Graphical AbstractOH -citronellol H 2 N NH 2 O Urea + SnCl 2 DMSO Air flow O NH 2 O -citronellyl Carbamate NH 3 + Ammonia β 0 3 0 6 0 9 0 0 20 40 60 80 100 (%) Time (min) β -Citronellol Conversion Selectivity β-Citronellyl Carbamate β

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Potential of some monoterpenoids and their new N-methyl carbamate derivatives against Schistosomiasis snail vector, Biomphalaria alexandrina

Cited by 21 publications

References 17 publications

Mediterranean essential oils as effective weapons against the West Nile vector Culex pipiens and the Echinostoma intermediate host Physella acuta: what happens around? An acute toxicity survey on non-target mayflies

Mediterranean essential oils as effective weapons against the West Nile vector Culex pipiens and the Echinostoma intermediate host Physella acuta: what happens around? An acute toxicity survey on non-target mayflies

Assessment of molluscicidal activity of essential oils from five Azorean plants against Radix peregra (Müller, 1774)

Tin-Catalyzed Urea Alcoholysis With β-Citronellol: A Simple and Selective Synthesis of Carbamates

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