含氮五元杂环酮的拟除虫菊酯的合成、结构和生物活性

以1-对乙氧基-2,2-二氯环丙烷甲酸(1a)和3-(2-氯-3,3,3-三氟-1-丙烯)-2,2-二甲基环丙烷甲酸(1b)为原料, 经酰氯化反应得到酰氯, 再以三乙胺为缚酸剂, 分别与2-烷酮、2-噻唑烷酮、2-噻唑硫酮、1-乙酰基-2-咪唑烷酮、1-甲磺酰 基-2-咪唑烷酮反应, 得到10个新的含氮五元杂环酮的拟除虫菊酯. 化合物结构经¹H NMR, IR, MS和元素分析进行表征. 并用X-ray单晶衍射测定了化合物3-(1-对乙氧基-2,2-二氯环丙烷甲酰)-2-噁唑烷酮(4a-1)的晶体结构. 对合成的化合物进行了初步的生物活性测试, 结果表明, 在试验浓度下部分目标化合物对黄瓜灰霉病菌具有一定得防效作用; 其中, 化合物(4a-1)和3-(3-(2-氯-3,3,3-三氟-1-丙烯)-2,2-二甲基环丙烷甲酰)-2-噻唑烷酮(4b-3)对粘虫也分别有50%及90%的杀虫活性.

Synthesis, Structure and Biological Activities of Pyrethroids with Ni-trogen Containing Five-Membered Heterocyclic Ketone Moieties

Ten new pyrethroids with nitrogen containing five-membered heterocyclic ketone moieties were synthesized by the reaction of 1-(4-ethoxyphenyl)-2,2-dichlorocyclopropane-1-carboxylic acid (1a) or 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropane-1-carboxylic acid (1b), with thionyl chloride, and then condensation reaction with 2-oxazolidinone, 2-thiazolidinethione, 2-thiazolidinone, 1-acetylimidazolidin-2-one and 1-(methylsulfonyl)imidazolidin-2-one respectively in the presence of triethylamine. Their structures were confirmed by ¹H NMR, IR, Mass Spectra and elemental analysis. The crystal structure of 3-(1-(4-ethoxyphenyl)-2,2-dichlorocyclopropylcarbonyl)oxazolidin-2-one (4a-1) was determined by X-ray diffraction analysis. The preliminary bioassay showed that some of the compounds exhibited certain fungicidal activities against Botrytis cinerea, 4a-1 and 3-(3-(2-chloro-3,3,3-trifluoro- prop-1-enyl)-2,2-dimethylcyclopropylcarbonyl)thiazolidin-2-one (4b-3) exhibited 50% and 90% in-hibition activities against Mythimnaseparate respectively.