新型含丁烯酸内酯基三氟乙基硫醚(亚砜)类化合物的设计、合成与杀螨活性
Design,synthesis and acaricidal activity of novel butenolide containing trifluoroethyl sulfide(sulfoxide)compounds
罗时燕 1陈锦彪 1林健 2田平义 2刘祈星 1周海峰1
作者信息
- 1. 三峡大学生物与制药学院天然产物研究与利用湖北省重点实验室绿色制药技术与工艺研究中心,湖北宜昌 443002
- 2. 顺毅股份有限公司台州市绿色农业化学品开发重点实验室,浙江台州 318000
- 折叠
摘要
为寻找高活性杀螨化合物,以sulfiflumin为先导化合物,保留 4-甲基-2-氟-5-(2,2,2-三氟乙硫基)苯胺活性基团,通过其与氯乙酰乙酸乙酯成环合成三氟乙基硫醚丁烯酸内酯的核心骨架C1,再对核心骨架进行氧化、氯代或溴代,以及将内酯环改造为硫内酯环及二硫代酮酯环得到C2～C8 7 个化合物,采用 1H NMR、13C NMR和HRMS手段对其结构进行了表征.生物活性测试数据表明,目标化合物在 100 mg/L质量浓度下具有一定的杀螨活性,尤其是对朱砂叶螨Tetranychus cinnabarinus卵孵化的抑制活性较高(校正孵化抑制率 67%～93%);此外,化合物C3 对二斑叶螨Tetranychus urticae成虫的的校正死亡率达 100%.该研究可为丁烯酸内酯基三氟乙基硫醚(亚砜)衍生物和氟吡呋喃酮衍生物的设计和改造提供研究思路,对探究该类化合物的生物活性具有参考意义.
Abstract
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.
关键词
丁烯酸内酯/三氟乙基硫醚(亚砜)类化合物/氟吡呋喃酮/朱砂叶螨/杀螨活性Key words
butenolide/trifluoroethyl sulfide(sulfoxide)/flupyradifurone/Tetranychus cinnabarinus/acaricidal activity引用本文复制引用
基金项目
顺毅股份有限公司研发项目(SDHZ2021215)
国家自然科学基金(22278244)
出版年
2024
国家科技期刊平台
NSTL
维普
万方数据