摘要
先将3-蒈烯分子中的碳碳双键氧化开环制得蒈酮酸,再将羰基还原成亚甲基得到蒈酸,酰氯化后与系列酰肼发生 N -酰化反应合成了14个新型蒈酸基双酰肼化合物( 5a^5n ),其结构经UV-Vis、 1 H NMR、 13 C NMR、 FT-IR和MS(ESI)表征,并测试了目标化合物的抑菌和除草活性。结果显示:在用药量为50 μg·mL -1 时,目标化合物对花生褐斑病菌、小麦赤霉病菌、黄瓜枯萎病菌、苹果轮纹病菌、番茄早疫病菌、玉米小斑病菌、西瓜炭疽病菌以及水稻纹枯病菌等8种植物病原菌具有一定的抑制活性,其中化合物蒈酸基α-噻吩甲酰肼 5f (R=α-thiophene)对苹果轮纹病菌的抑制率达85.0%,优于阳性对照百菌清。在用药量为100 μg·mL -1 时,化合物蒈酸基3′,4′-二甲氧基苯甲酰肼 5j (R=3′,4′-OMe-Ph)、蒈酸基 m -甲氧基苯甲酰肼 5d (R= m -OMe-Ph)、蒈酸基 m -甲基苯甲酰肼 5b (R= m -Me-Ph)和蒈酸基苯甲酰肼 5a (R=Ph)对油菜胚根生长的抑制率分别为88.5%、 86.1%、 85.1%和82.6%(均为A级活性水平),优于阳性对照丙炔氟草胺。
Caronic acid was prepared at first by oxidative cleavage of the C=C bond in the molecule of 3-carene, followed by reduction of the carbonyl group into methylene. Then, fourteen novel caric acid-based diacylhydrazine compounds( 5a^5n ) were synthesized by N -acylation reaction of the acyl chloride of caric acid with a series of substituted acylhydrazines. The structures were characterized by means of UV-Vis, 1 H NMR, 13 C NMR, FT-IR and MS(ESI). The antifungal and herbicidal activities were preliminarily evaluated as well. As indicated in bioassay results, at 50 μg·mL -1 , all the target compounds exhibited certain inhibition activity against eight tested plant pathogens, including Cercospora arachidicola , Gibberella zeae, Fusarium oxysporum f. sp. cucumerinum , Physalospora piricola , Alternaria solani , Bipolaris maydis , Colleterichum orbicalare, and Rhzioeotnia solani . The inhibition rate of compound caric acid-based α-thiophenyl acylhydrazine 5f (R=α-thiophene) against Physalospora piricola was 85.0%, showing better antifungal activity than that of the positive control chlorothanil. Also, at 100 μg·mL -1 , compounds caric acid-based 3′,4′-dimethoxybenzoyl acylhydrazine 5j (R=3′,4′-OMe-Ph), 5d caric acid-based m -methoxybenzoyl acylhydrazine(R= m -OMe-Ph), caric acid-based m -methylbenzoyl acylhydrazine 5b (R= m -Me-Ph), and caric acid-based benzoyl acylhydrazine 5a (R=Ph) displayed prominent herbicidal activity of 88.5%, 86.1%, 85.1%, and 82.6%(all in A-class activity level), respectively, against the root-growth of rape( B. campestris ), showing better herbicidal activity than that of the positive control flumioxazin.
作者
虞友培
段文贵
林桂汕
康国强
王晓宇
岑波
雷福厚
YU You-pei;DUAN Wen-gui;LIN Gui-shan;KANG Guo-qiang;WANG Xiao-yu;CEN Bo;LEI Fu-hou(College of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, China;Guangxi Key Laboratory of Chemistry and Engineering of Forest Products,Guangxi University for Nationalities, Nanning 530006, China)
出处
《合成化学》
CAS
北大核心
2019年第9期689-697,共9页
Chinese Journal of Synthetic Chemistry
基金
国家自然科学基金资助项目(31870556)
广西科技基地和人才专项(桂科AD18126005)
关键词
3-蒈烯
酰肼
蒈酸基双酰肼
合成
抑菌活性
除草活性
3-carene
acylhydrazine
caric acid-based diacylhydrazine
synthesis
antifungal activity
herbicidal activity
