Design,synthesis and acaricidal activity of novel butenolide containing trifluoroethyl sulfide(sulfoxide)compounds
In order to discover new acaricides with high activity,the lead compound sulfiflumin was modified,a series of novel butenolide containing trifluoroethyl sulfide(sulfoxide)compounds were designed and synthesized.First,butenolide containing trifluoroethyl sulfide(sulfoxide)C1 as a key compound was synthesized from the highly active fragment 4-methyl-2-fluoro-5-(2,2,2-trifluoroethyl thiothionyl)aniline and ethyl chloroacetoacetate.Then C2-C8 were synthesized by oxidation,chlorination or bromination of compound C1,or replacement with thiolact-one ring and dithioketone ester ring.The target compounds were characterized by 1H NMR,13C NMR and HRMS.Acaricidal activity showed that compounds C1-C8 had certain acaricidal activity,especially for the egg of Tetranychus cinnabarinus with 67%-93%activity.Moreover,the mortality rate of compound C3 against adults Tetranychus urticae was 100%.This work provides a guideline for the modification of butenolide containing trifluoroethyl sulfide(sulfoxide)compounds and flupyradifurone and is of reference significance for exploring biological activities.
国家科技期刊平台
NSTL
万方数据
维普
