含硒邻苯二甲酰胺类新化合物的合成、结构表征及杀虫活性

Synthesis,Characterization and Insecticidal Activity of Phthalamide Compounds Containing Selenium Fragment

[方法]为获得新型鱼尼汀受体类杀虫剂,以3-碘苯酐及2-甲基-1-甲硒基-2-丙胺为起始原料,经缩合反应、关环及开环反应制备了系列含硒的邻苯二甲酰胺类新化合物(5a-5i,收率46%-50%),以核磁共振氢谱及元素分析等手段对中间体、终产物结构进行了表征。[结果]杀虫活性筛选表明化合物5a、5d、5h、5i在100 mg/L质量浓度下对小菜蛾杀死率达到90%以上。[结论]通过构效关系的分析得知:以先导物氟虫酰胺为对照,改变脂肪胺部分为含硒片段,活性总体下降;芳香胺的氨基对位为二氯烯丙氧基时,氨基邻位的卤原子对杀虫活性具有促进作用。

[Methods] To obtain new ryanodine receptor insectcide,novel phthalamides（5a-5i） containing selenium fragment were synthesized via condensation,ring-close and then ring-openning starting from 3-iodophthalic anhydride and 2-methyl-1-methylseleno-2-propanamine with 46-50% yield All intermediates and target compounds were characterized by 1H NMR and elemental analysis techniques.[Results] At a concentration of 100 mg/L,5a,5d,5h and 5i showed above 90% insecticidal activity toward Plutella xylostella according to the bioassays.[Conclusions] When aliphatic amine was changed with a selenium fragment,The insecticidal activity of phthalamides decreased compared with flubendiamide.While containing dichloroallyloxyl group at the paraposition of the amino group in the arylamine moiet,the ortho-halogen promoted notablely the insecticidal activity of the compounds containing selenium.