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.