含肟醚并取代异 NFDA1唑环的氨基甲酸酯类化合物的合成及生物活性

为寻找具有优异生物活性的氨基甲酸酯类化合物,根据活性亚结构拼接原理,将取代异 NFDA1 唑和肟醚基团引入多菌灵结构中,以取代苯甲醛 (1) 和2-氯苄胺(3) 为起始原料,经多步反应设计合成了10个未见文献报道的含肟醚并取代异 NFDA1 唑的氨基甲酸酯类化合物,其结构经 1H NMR 和 MS 确证。初步生物活性测定结果表明,部分目标化合物不仅具有一定的杀菌活性,同时还具有较好的除草活性。其中,活体盆栽试验结果表明,化合物11b对黄瓜霜霉病Pseudoperonospora cubensis 的相对防效为90%,对黄瓜白粉病Sphaerotheca fuliginea 的相对防效达95%,低于对照药剂多菌灵;除草活性皿测法表明,化合物11c和11j 200 mg/L下对靶标作物的根、茎抑制率均达80%以上,与对照药剂异丙酯草醚活性相当。盆栽法表明,150 g/hm2下,化合物11c和11j对繁缕Stellaria media苗前和苗后的抑制率均在70%以上,低于异丙酯草醚。此类化合物的构效关系有待进一步研究。

Synthesis and biological activity of novel carbamates containing methoxyimino-isoxazoline

To search for novel carbamates with unique biological activities, novel compounds were designed by splicing active groups oxime ether and isoxazoline into carbendazim. 10 Novel title compounds were synthesized from substitutional benzaldehydes (1) and 2-chlorobenzylamine (3) in multiple steps. The structures of the compounds were confirmed by MS and ¹H NMR. The bioassays showed that the compounds exhibit both good fungicidal activity and herbicidal activity. Among them, with the small plant pot spray method, fungicidal efficacies of 11b were 90% against Pseudoperonospora cubensis and 95% against Sphaerotheca fuliginea at 200 mg/L, lower than carbendazim. The preliminary herbicidal screening showed that the inhibition rates of 11c and 11j were up to 80% against root and stem growth of all the target plants, nearly as good as pyribambenz isopropyl. However, the secondary herbicidal screening showed that the herbicidal efficacies of 11c and 11j against Stellaria media were up to 70% both by postmergence foliar spray and preemergence soil spray processing at 150 g/hm², lower than pyribambenz isopropyl. The relationship between structure and biological activity was also studied.