Paula Vanderlúcia F, Barbosa Luiz Cláudio A, Teixeira Róbson R, Picanço Marcelo C, Silva Gerson A
Department of Chemistry, Federal University of Viçosa, Av. PH Rolfs, 36570-000 Viçosa, MG, Brazil.
Pest Manag Sci. 2008 Aug;64(8):863-72. doi: 10.1002/ps.1559.
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.
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.
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.
合成了一系列3-苄基呋喃-2-基N，N，N'，N'-四乙基二氨基磷酸酯衍生物作为潜在的新型昆虫防治剂。通过红外光谱、核磁共振和质谱分析确定了它们的结构。
由呋喃-2-基N'（N，N，N'，N'-四乙基二氨基磷酸酯）制备了10种3-苄基呋喃-2-基N，N，N'，N'-四乙基衍生物。以10μg mg(-1)昆虫的剂量评估了所有衍生物对四种昆虫的接触毒性，这四种昆虫分别是：Ascia monuste orseis Latr.（鳞翅目：螟蛾科）、透明裳夜蛾（Diaphania hyalinata (L.)，鳞翅目：螟蛾科）、玉米象（Sitophilus zeamais Mots.，鞘翅目：豆象科）和红火蚁（Solenopsis saevissima (Smith)，膜翅目：蚁科）。观察到一些衍生物的死亡率范围，如3-(3-甲基苄基)呋喃-2-基N，N，N'，N'-四乙基二氨基磷酸酯（对透明裳夜蛾的死亡率为82.5%；对红火蚁的死亡率为100%），与市售杀虫剂甲基毒死蜱相当。衍生物的生物活性取决于苄基环的取代模式。还评估了呋喃-2-基N，N，N'，N'-四乙基二氨基磷酸酯、呋喃-2-基N，N-二乙基氨基氯磷酸酯和二呋喃-2-基N，N-二乙基氨基磷酸酯，在某些情况下，它们的活性与甲基毒死蜱相当（分别对Ascia monuste orseis的死亡率为90%、100%和97.5%）。对一些评估的呋喃-2(5H)-酮观察到了相当的活性。
合成了10种3-苄基呋喃-2-基N，N，N'，N'-四乙基二氨基磷酸酯衍生物，并从化学角度进行了充分表征。生物测定结果表明，这类化合物可用于设计具有杀虫活性的新物质。
