3-(2-氯-4-三氟甲基)苯氧基取代苯甲酰腙衍生物的合成与生物活性
收稿日期: 2012-04-20
修回日期: 2012-05-24
网络出版日期: 2012-06-05
基金资助
国家重点基础研究发展规划(973计划) (No. 2010CB126100)、国家自然科学基金(Nos. 20372023, 20772042)资助项目.
Synthesis and Pesticidal Activity of 3-(2-Chloro-4-trifluoromethyl)phenoxy Benzoylhydrazones
Received date: 2012-04-20
Revised date: 2012-05-24
Online published: 2012-06-05
Supported by
Project supported by the National Basic Research Program of China (No. 2010CB126100), and the National Natural Science Foundation of China (Nos. 20372023, 20772042).
选择3-(2-氯-4-三氟甲基苯氧基)苯甲酸为起始原料, 经酰氯化, 再与乙醇反应成酯, 然后和水合肼反应, 最后与芳香醛缩合, 合成了10个未见文献报道的3-(2-氯-4-三氟甲基苯氧基)苯甲酰腙4. 通过IR, 1H NMR, EI-MS, 元素分析等方法对所合成的化合物进行了结构表征. 代表化合物4-氯苯亚甲基-3-(2-氯-4-三氟甲基苯氧基)苯甲酰腙(4f)经单晶X衍射证实了结构. 并初步测定了所合成化合物的杀菌和除草活性. 结果表明: 部分测试化合物在50 mg/L浓度下对水稻纹枯菌和黄瓜灰霉菌具有优良的抑制效果, 在100 mg/L浓度下对油菜和稗草的根显示一定的抑制效果.
刘建超 , 崔泽平 , 贺红武 . 3-(2-氯-4-三氟甲基)苯氧基取代苯甲酰腙衍生物的合成与生物活性[J]. 有机化学, 2012 , 32(10) : 1925 -1929 . DOI: 10.6023/cjoc201204022
A series of new substituted benzaldehyde (or 2-furaldehyde) 3-(2-chloro-4-trifluoromethyl)phenoxy benzoylhy- drazones 4 have been designed and synthesized by the reactions of substituted aldehydes with intermediate 3 in 64%～89% yields. The structures of compounds 4 have been confirmed by 1H NMR, IR, EI-MS and elemental analyses. The structure of 4-chloro-benzaldehyde 3-(2-chloro-4-trifluoromethyl)phenoxy benzoylhydrazone (4f) has been determined by X-ray single crystal diffraction. The results of preliminary bioassay indicated that some compounds possess good fungicidal activities against Rhizoctonia solani and Botrytis cinereapers at a dosage of 50 mg/L and moderate herbicidal activity against the roots of rape and barnyard grass at 100 mg/L.
Key words： benzaldehyde; benzoylhydrazone; fungicidal activity; herbicidal activity
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