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Paula VF, Barbosa LC, Teixeira RR, Picanco MC, Silva GA: Synthesis and insecticidal activity of new 3-benzylfuran-2-yl N,N,N',N'-tetraethyldiamidophosphate derivatives. Pest Manag Sci. 2008 Aug;64(8):863-72.
BACKGROUND: A series of 3-benzylfuran-2-yl N,N,N',N'-tetraethyldiamidophosphate derivatives were synthesized as potential new agents to control insects. Their structures were confirmed on the basis of IR, NMR and MS analyses. RESULTS: Ten 3-benzylfuran-2-ylN,N,N',N'-tetraethyl derivatives were prepared from the compound furan-2-yl N' (N,N,N',N'-tetraethyldiamidophosphate). The contact toxicity of all derivatives, at a dose of 10 microg mg (-1) insect, was evaluated against four insect species, Ascia monuste orseis Latr. (Lepidoptera: Pyralidae), Diaphania hyalinata (L.) (Lepidoptera: Pyralidae), Sitophilus zeamais Mots. (Coleoptera: Bruchidae) and Solenopsis saevissima (Smith) (Hymenoptera: Formicidae). The mortality range observed for some derivatives, such as 3-(3-methylbenzyl) furan-2-yl N,N,N',N'-tetraethyldiamidophosphate (82.5% mortality against D. hyalinata; 100% mortality against S. saevissima), was comparable with that of the commercial insecticide chlorpyrifos-methyl. The biological activity of the derivatives depended on the substitution pattern of the benzylic ring. Furan-2-yl N,N,N',N'-tetraethyldiamidophosphate, furan-2-yl N,N-diethylamidochlorophosphate and difuran-2-yl N,N-diethylamidophosphate were also evaluated, displaying, in some cases, activity comparable with that of chlorpyrifos-methyl (90%, 100% and 97.5% respectively against A. monuste orseis). Considerable activity was observed for some furan-2 (5H)-ones evaluated. CONCLUSION: Ten 3-benzylfuran-2-yl N,N,N',N'-tetraethyldiamidophosphate derivatives were synthesized and fully characterized from a chemical point of view. The results obtained from the biological assays indicate that this class of compounds can be utilized for the design of new substances endowed with insecticidal activity. |
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