氨基甲酸-2-氯吡啶-5-甲酯化合物的合成与抑菌活性

以芳香硝基化合物、2-氯-5-吡啶甲醇和一氧化碳为原料,在Pd-Fe/TiO2催化下进行羰基化反应,合成了11个新型氨基甲酸-2-氯吡啶-5-甲酯化合物,其结构经 1H NMR和MS表征。初步抑菌活性测定结果表明:在50 mg/L下,大多数目标化合物对4种供试病原菌具有一定的抑制活性,其中化合物 3f (4-甲氧基苯基氨基甲酸-2-氯吡啶-5-甲酯、3h (2,4-二氯苯基氨基甲酸-2-氯吡啶-5-甲酯)和 3j (3,4-二氯苯基氨基甲酸-2-氯吡啶-5-甲酯)对小麦赤霉病菌Gibberella zeae的抑制率达77.3%以上, 3f 对苹果轮纹病菌Physalospora piricola的抑制率达82.5%,与对照药多菌灵接近;所有化合物在50 mg/L下对番茄灰霉病菌Botrytis cinerea的抑制活性均优于对照药多菌灵。

Synthesis and fungicidal activity of (2-chloropyridin-5-yl) methyl carbamates

Eleven novel(2-chloropyridin-5-yl)methyl carbamates were synthesized by Pd-Fe/TiO₂ catalyzed carbonylation of aromatic nitro-compounds and(2-chloropyridin-5-yl)methanol with carbon monoxide. Their structures were confirmed by ¹H NMR and MS. Preliminary fungicidal activity tests indicated that some of the target compounds exhibited certain degree of inhibiting effect against four tested strains at the concentration of 50 mg/L. The inhibition rate against Gibberella zeae was over 77.3% for compound 3f [(2-chloropyridin-5-yl) methyl(4-methoxyphenyl)carbamate], 3h [2-chloropyridin-5-yl)methyl(2,4-dichlorophenyl)carbamate] and 3j [(2-chloropyridin-5-yl) methyl(3,4-dichlorophenyl) carbamate]. Compound 3f showed 82.5% of inhibition rate against Physalospora piricola, that was almost equal to carbendazim. All compounds showed better fungicidal activities against Botrytis cinerea than carbendazim.