新型苯并咪唑衍生物的合成及其生物活性

以香草醛为原料,经2步反应制得中间体——2-(4-羟基-3-甲氧基苯基)-1-氢-苯并咪唑(3);3分别与取代苯甲酰氯,取代苯乙酰氯和取代苯磺酰氯反应,合成了13个新型的苯并咪唑衍生物(7a~7g,8a,8d,8g,9a,9d和9g),其结构经~1H NMR,IR和HR-ESI-MS表征。分别用菌丝生长速率法和曹坳程法测试了7~9的抑菌活性和除草活性。结果表明:c=100 mg·L~(-1)时,7~9对番茄灰霉病菌,油菜菌核病菌和稻瘟病菌的抑制率分别为13.79%~65.38%,13.88%~63.78%和34.22%~58.79%;c=300 mg·L~(-1)时,7g对稗草和反枝苋的芽长抑制率分别为40.20%和80.84%。

Synthesis and Bioactivities of Novel Benzimidazole Derivatives

The intermediate , 2-( 4-hydroxy-3-methoxyphenyl )-1-H-benzimidazole ( 3 ) , was prepared by a two-step reaction from vanilline.Thirteen novel benzimidazole derivatives (7a~7g, 8a, 8d, 8g, 9a, 9d and 9g) were synthesized by the reaction of 3 with substituted benzoyl chloride , substituted phenylacetyl chloride and substituted phenylsulfonyl chloride , respectively .The structures were char-acterized by 1 H NMR, IR and HR-ESI-MS.The antifungicidal and herbicidal activities were investiga-ted by mycelium growth rate method and Cao Ao-cheng method , respectively .The results indicated that the inhibition rates of 7~9 against Botrytis cinerea, Sclerotinia sclerotiorum and Pyricularia grisea were 13.79%~65.38%, 13.88%~63.78%and 34.22%~58.79%, respectively, at the concen-tration of 100 mg· L-1 .7g exhibited good herbicidal activities against Echinochloa crusgalli and Ama-ranthus retroflexus at the concentration of 300 mg · L-1 .The inhibition rates were 40.20% and 80 .84%, respectively .