A series of novel aryl [(N,N'-diacyl-N'-tert-butylhydrazino)thio]methylcarbamates were synthesized by the reaction of aryl (chlorothio)methylcarbamates with N,N'-diacyl-N-tert-butylhydrazines in the presence of sodium hydride. X-Ray single crystal diffraction of 2-isobutylphenyl [(N,N'-dibenzoyl-N'-tert-butylhydrazino)thio]methylcarbamate demonstrated the presence of N-S-N bonding. All of the compounds exhibited excellent larvicidal activities. Toxicity assays indicated that the products had knockdown activities of aryl methylcarbamates at higher concentrations and insect growth regulator activities of diacylhydrazines at lower concentrations.
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http://dx.doi.org/10.1002/ps.1073 | DOI Listing |
Pestic Biochem Physiol
October 2018
Emerging Pathogens Institute and Department of Entomology and Nematology, University of Florida, Gainesville, FL 32610, USA.
The widespread emergence of pyrethroid-resistant has intensified the need to find new contact mosquitocides for indoor residual spraying and insecticide treated nets. With the goal of developing new species-selective and resistance-breaking acetylcholinesterase (AChE)-inhibiting mosquitocides, in this report we revisit the effects of carbamate substitution on aryl carbamates, and variation of the 1-alkyl group on pyrazol-4-yl methylcarbamates. Compared to aryl methylcarbamates, aryl dimethylcarbamates were found to have lower selectivity for AChE (AChE) over human AChE (hAChE), but improved tarsal contact toxicity to G3 strain .
View Article and Find Full Text PDFChem Biol Interact
March 2013
Department of Chemistry, Virginia Tech, Blacksburg, VA 240161, USA.
New carbamates that are highly selective for inhibition of Anopheles gambiae acetylcholinesterase (AChE) over the human enzyme might be useful in continuing efforts to limit malaria transmission. In this report we assessed 34 synthesized and commercial carbamates for their selectivity to inhibit the AChEs found in carbamate-susceptible (G3) and carbamate-resistant (Akron) An. gambiae, relative to human AChE.
View Article and Find Full Text PDFBioorg Med Chem Lett
July 2012
Department of Chemistry, Virginia Tech, Blacksburg, VA 24061, USA.
To identify potential human-safe insecticides against the malaria mosquito we undertook an investigation of the structure-activity relationship of aryl methylcarbamates inhibitors of acetylcholinesterase (AChE). Compounds bearing a β-branched 2-alkoxy or 2-thioalkyl group were found to possess good selectivity for inhibition of Anopheles gambiae AChE over human AChE; up to 530-fold selectivity was achieved with carbamate 11d. A 3D QSAR model is presented that is reasonably consistent with log inhibition selectivity of 34 carbamates.
View Article and Find Full Text PDFChem Commun (Camb)
January 2011
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, PR China.
A tandem NHC-catalyzed aza-benzoin/Michael reaction has been developed as a method to efficiently produce dihydroindenones and pyrrolidinone-containing tricycles. The novel reaction pattern involves tert-butyl aryl(tosyl)methylcarbamates reacting as both electrophile and nucleophile on the same carbon.
View Article and Find Full Text PDFFEBS J
July 2007
Institut de Biologia Molecular de Barcelona, Consejo Superior de Investigaciones Científicas, Barcelona, Spain.
Carbaryl (1-naphthyl-N-methylcarbamate), a widely used carbamate insecticide, induces cytochrome P450 1A gene expression in mammalian cells. This activity is usually mediated by the interaction of the compound with the aryl hydrocarbon receptor. However, it has been proposed that this mechanism does not apply to carbaryl because its structure differs from that of typical aryl hydrocarbon receptor ligands.
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