title: Synthesis and biological activity of fluorescent neonicotinoid insecticide thiamethoxam.
abstract: Here, we describe the synthesis of two new fluorescent derivatives of thiamethoxam and compared their toxicity on aphid Acyrthosiphon pisum and their mode of action on insect nicotinic acetylcholine receptors expressed on the sixth abdominal ganglion. The compound 3 with two 2-chlorothiazole moieties was found to be more toxic using toxicological bioassays 24 h and 48 h after exposure while compound 4 appeared more active using cockroach ganglionic depolarization. Interestingly, thiamethoxam appeared more effective than component 3 and 4, respectively. Our results demonstrated that component 3 and 4 act as agonists of insect nicotinic acetylcholine receptors.
authors.affiliation: Laboratoire Récepteurs et Canaux Ioniques Membranaires (RCIM), UPRES EA 2647/USC INRA 1330, SFR 4207 QUASAV, Université d'Angers, UFR sciences, 2 Bd. Lavoisier, 49045 Angers, France.
authors.forename: Emiliane
authors.initials: E
authors.lastname: Taillebois
authors.affiliation: Laboratoire Récepteurs et Canaux Ioniques Membranaires (RCIM), UPRES EA 2647/USC INRA 1330, SFR 4207 QUASAV, Université d'Angers, UFR sciences, 2 Bd. Lavoisier, 49045 Angers, France.
authors.forename: Paul
authors.initials: P
authors.lastname: Langlois
authors.affiliation: Laboratoire Substances d'Origine Naturelle et Analogues Structuraux (SONAS), UPRES EA 921/SFR 4207 QUASAV, UFR Sciences Pharmaceutiques, 16 Bd. Daviers, 49045 Angers Cedex 01, France.
authors.forename: Thomas
authors.initials: T
authors.lastname: Cunha
authors.affiliation: Laboratoire Substances d'Origine Naturelle et Analogues Structuraux (SONAS), UPRES EA 921/SFR 4207 QUASAV, UFR Sciences Pharmaceutiques, 16 Bd. Daviers, 49045 Angers Cedex 01, France.
authors.forename: Denis
authors.initials: D
authors.lastname: Seraphin
authors.affiliation: Laboratoire Récepteurs et Canaux Ioniques Membranaires (RCIM), UPRES EA 2647/USC INRA 1330, SFR 4207 QUASAV, Université d'Angers, UFR sciences, 2 Bd. Lavoisier, 49045 Angers, France. Electronic address: steeve.thany@univ-angers.fr.
authors.forename: Steeve H
authors.initials: SH
authors.lastname: Thany
mesh_terms: D000818:Animals; D001042:Aphids / Q000187:drug effects*; D004305:Dose-Response Relationship, Drug; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D007306:Insecticides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D008968:Molecular Conformation; D000073943:Neonicotinoids; D009574:Nitro Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D010078:Oxazines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D011978:Receptors, Nicotinic / Q000378:metabolism*; D013329:Structure-Activity Relationship; D000077922:Thiamethoxam; D013844:Thiazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D005456:Fluorescent Dyes; D007306:Insecticides; D000073943:Neonicotinoids; D009574:Nitro Compounds; D010078:Oxazines; D011978:Receptors, Nicotinic; D013844:Thiazoles; D000077922:Thiamethoxam
keywords: Insect; Insecticide; Neonicotinoid; Nicotinic receptor; Thiamethoxam