4-(7-甲氧基-2,2-二甲基-2,3-二氢苯并呋喃-5-基)-2-芳氨基噻唑的合成、晶体结构与杀虫活性

以2-(2-甲基烯丙氧基)苯酚为原料, 经Claisen重排、呋喃环化、醚化、Friedel-Crafts乙酰化、α-溴代和噻唑环化等反应合成了22种4-(7-甲氧基-2,2-二甲基-2,3-二氢苯并呋喃-5-基)-2-芳氨基噻唑化合物. 化合物的结构经质谱、1H NMR和元素分析等确证. 采用单晶X射线衍射仪测定了化合物7j的晶体结构, 该晶体属于单斜晶系, 空间群为C2/c, 晶胞参数a=2.21140(12) nm, b=0.87602(5) nm, c=2.13911(12) nm, β=115.5380(10)°; V=3.7391(4) nm3, Z=8, Dc=1.375 g/cm3, F(000)=1616, S=1.046, μ=0.333 mm-1, 最终偏差因子R1=0.0390, wR2=0.1079. 杀虫活性实验结果表明, 化合物7a, 7b, 7h和7t在浓度为500 mg/L时对蚕豆蚜死亡率分别为95.12%, 62.60%, 57.53%和59.06%.

Synthesis, Crystal Structure and Insecticidal Activity of 4- ( 7-Methoxy-2,2 -dimethyl-2,3 -dihydrobenzofuran-5 -yl ) -N- ( aryl ) thiazol-2-amine

In order to find novel insecticides with high activity, a series of 4-(7-methoxy-2,2-dimethyl-2,3-dihydrobenzofuran-5-yl)-N-(aryl)thiazol-2-amines was synthesized from 2-(2-methylallyloxy)phenol with Claisen rearrangement, cyclization of furan, etherification, Friedel-Crafts acylation, α-bromation and cyclization of thiazole. Their structures were  confirmed by mass spectrometry(MS), 1H NMR spectra and elemental analysis. The crystal structure of compound 7j was determined by X-ray diffraction analysis. The crystal belongs to the monoclinic system, space group C2/c with a=2.21140(12) nm, b=0.87602(5) nm, c=2.13911(12) nm, β=115.5380(10)°; V=3.7391(4) nm3, Z=8, Dc=1.375 g/cm3, F(000)=1616, S=1.046, μ=0.333 mm-1, the final R1=0.0390 and wR2=0.1079. The preliminary bioassays indicated that compound 7a, 7b, 7h and 7t exhibited insecticidal activity against Aphis fabae were 95.12%, 62.60%, 57.53% and 59.06%, respectively, at 500 mg/L.