Bioefficacy of acyclic monoterpenes and their saturated derivatives against the West Nile vector Culex pipiens

dc.contributor.author	Michaelakis, A	en
dc.contributor.author	Vidali, VP	en
dc.contributor.author	Papachristos, DP	en
dc.contributor.author	Pitsinos, EN	en
dc.contributor.author	Koliopoulos, G	en
dc.contributor.author	Couladouros, EA	en
dc.contributor.author	Polissiou, MG	en
dc.contributor.author	Kimbaris, AC	en
dc.date.accessioned	2014-06-06T06:52:59Z
dc.date.available	2014-06-06T06:52:59Z
dc.date.issued	2014	en
dc.identifier.issn	00456535	en
dc.identifier.uri	http://dx.doi.org/10.1016/j.chemosphere.2013.07.032	en
dc.identifier.uri	http://62.217.125.90/xmlui/handle/123456789/6288
dc.subject	Acyclic monoterpenes	en
dc.subject	Culex pipiens	en
dc.subject	Larvicide	en
dc.subject	Repellency	en
dc.subject	Structure-activity relationships	en
dc.subject.other	Acyclic monoterpenes	en
dc.subject.other	Culex pipiens	en
dc.subject.other	Larvicide	en
dc.subject.other	Repellency	en
dc.subject.other	Structure activity relationships	en
dc.subject.other	Functional groups	en
dc.subject.other	Isomers	en
dc.subject.other	Monoterpenes	en
dc.subject.other	Toxicity	en
dc.subject.other	Volatile fatty acids	en
dc.subject.other	alcohol derivative	en
dc.subject.other	benzoyl peroxide	en
dc.subject.other	beta citral	en
dc.subject.other	carbonyl derivative	en
dc.subject.other	carboxyl group	en
dc.subject.other	carboxylic acid	en
dc.subject.other	citral	en
dc.subject.other	citronellic acid	en
dc.subject.other	citronellol	en
dc.subject.other	citronellyl acetate	en
dc.subject.other	diethyltoluamide	en
dc.subject.other	dihydrocitronellal	en
dc.subject.other	dihydrocitronellol	en
dc.subject.other	dihydrocitronellyl acetate	en
dc.subject.other	dihydrolinalool	en
dc.subject.other	dihydrolinalyl acetate	en
dc.subject.other	ester	en
dc.subject.other	geraniol	en
dc.subject.other	geranyl acetate	en
dc.subject.other	hydroxyl group	en
dc.subject.other	icaridin	en
dc.subject.other	insect repellent	en
dc.subject.other	larvicidal agent	en
dc.subject.other	linalool	en
dc.subject.other	linalyl acetate	en
dc.subject.other	nerol	en
dc.subject.other	neryl acetate	en
dc.subject.other	terpene	en
dc.subject.other	tetrahydrolinalyl acetate	en
dc.subject.other	unclassified drug	en
dc.subject.other	vinyl derivative	en
dc.subject.other	acetate	en
dc.subject.other	bioassay	en
dc.subject.other	disease vector	en
dc.subject.other	functional group	en
dc.subject.other	mosquito	en
dc.subject.other	oxidation	en
dc.subject.other	repellent	en
dc.subject.other	saturation	en
dc.subject.other	toxicity	en
dc.subject.other	article	en
dc.subject.other	chemical bond	en
dc.subject.other	chemical composition	en
dc.subject.other	chemical structure	en
dc.subject.other	controlled study	en
dc.subject.other	Culex pipiens	en
dc.subject.other	hydrogenation	en
dc.subject.other	insecticidal activity	en
dc.subject.other	LC 50	en
dc.subject.other	nonhuman	en
dc.subject.other	oxidation	en
dc.subject.other	reduction	en
dc.subject.other	synthesis	en
dc.subject.other	toxicity testing	en
dc.subject.other	Culex pipiens	en
dc.title	Bioefficacy of acyclic monoterpenes and their saturated derivatives against the West Nile vector Culex pipiens	en
heal.type	journalArticle	en
heal.identifier.primary	10.1016/j.chemosphere.2013.07.032	en
heal.publicationDate	2014	en
heal.abstract	Twenty acyclic monoterpenes with different functional groups (acetoxy, hydroxyl, carbonyl and carboxyl) bearing a variable number of carbon double bonds were assayed as repellent and larvicidal agents against the West Nile vector Culex pipiens. Seven of them were derivatives that were synthesized through either hydrogenation or oxidation procedures. All repellent compounds were tested at the dose of 1mgcm-2 and only neral and geranial were also tested at a 4-fold lower dose (0.25mgcm-2). Repellency results revealed that geranial, neral, nerol, citronellol, geranyl acetate and three more derivatives dihydrolinalool (3), dihydrocitronellol (5) and dihydrocitronellyl acetate (6) resulted in no landings. Based on the LC50 values the derivative dihydrocitronellyl acetate (6) was the most active of all, resulting in an LC50 value of 17.9mgL-1. Linalyl acetate, citronellyl acetate, neryl acetate, geranyl acetate, dihydrocitronellol (5), dihydrocitronellal (7), citronellol, dihydrolinalyl acetate (2), citronellic acid and tetrahydrolinalyl acetate (1) were also toxic with LC50 values ranging from 23 to 45mgL-1. Factors modulating toxicity have been identified, thus providing information on structural requirements for the selected acyclic monoterpenes. The acetoxy group enhanced toxicity, without being significantly affected by the unsaturation degree. Within esters, reduction of the vinyl group appears to decrease potency. Presence of a hydroxyl or carbonyl group resulted in increased activity but only in correlation to saturation degree. Branched alcohols proved ineffective compared to the corresponding linear isomers. Finally, as it concerns acids, data do not allow generalizations or correlations to be made. © 2013 Elsevier Ltd.	en
heal.journalName	Chemosphere	en
dc.identifier.volume	96	en
dc.identifier.doi	10.1016/j.chemosphere.2013.07.032	en
dc.identifier.spage	74	en
dc.identifier.epage	80	en