Synthesis and Insecticidal Activity of an Oxabicyclolactone and Novel Pyrethroids
| Autor: | Elizeu S. Farias, Elson S. Alvarenga, Marcelo Coutinho Picanço, Gabriela C. Resende, Vânia M.T. Carneiro, Mayara Cristina Lopes |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2012 |
| Předmět: |
Insecticides
Insecta Pharmaceutical Science Alcohol Furfural Article oxabicyclo Analytical Chemistry lcsh:QD241-441 chemistry.chemical_compound Lactones lcsh:Organic chemistry Drug Discovery Nitriles Pyrethrins Organic chemistry Animals Furaldehyde Mannitol Physical and Theoretical Chemistry Pyrethroid photochemistry Molecular Structure pyrethroid Organic Chemistry insecticide Biological activity Isopropyl alcohol furfural Pesticide Deltamethrin chemistry Chemistry (miscellaneous) Yield (chemistry) Molecular Medicine |
| Zdroj: | Molecules, Vol 17, Iss 12, Pp 13989-14001 (2012) Molecules Molecules; Volume 17; Issue 12; Pages: 13989-14001 |
| ISSN: | 1420-3049 |
| Popis: | Deltamethrin, a member of the pyrethroids, one of the safest classes of pesticides, is among some of the most popular and widely used insecticides in the World. Our objective was to synthesize an oxabicyclolactone 6 and five novel pyrethroids 8–12 from readily available furfural and D-mannitol, respectively, and evaluate their biological activity against four insect species of economic importance namely A. obtectus, S. zeamais, A. monuste orseis, and P. americana. A concise and novel synthesis of 6,6-dimethyl-3-oxabicyclo[3.1.0]hexan-2-one (6) from furfural is described. Photochemical addition of isopropyl alcohol to furan-2(5H)-one afforded 4-(1'-hydroxy-1'-methylethyl)tetrahydro-furan-2-one (3). The alcohol 3 was directly converted into 4-(1'-bromo-1'-methylethyl)-tetrahydrofuran-2-one (5) in 50% yield by reaction with PBr3 and SiO2. The final step was performed by cyclization of 5 with potassium tert-butoxide in 40% yield. The novel pyrethroids 8–12 were prepared from methyl (1S,3S)-3-formyl-2,2-dimethylcyclopropane-1-carboxylate (7a) by reaction with five different aromatic phosphorous ylides. Compounds 6–12 presented high insecticidal activity, with 6 and 11 being the most active. Compound 6 killed 90% of S. zeamais and 100% of all the other insects evaluated. Compound 11 killed 100% of all insects tested. |
| Databáze: | OpenAIRE |
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