Synthesis and Herbicidal Activity of Novel Cyanoacrylate Derivatives Containing Substituted Oxazole Moiety

被引:8
作者
Shi, Yujun [1 ]
Du, Xianchao [1 ]
Wang, Xianglong [1 ]
Chen, Qingwen [1 ]
Li, Ling [1 ]
Dai, Hong [1 ]
Xu, Caiqin [1 ]
Zhang, Jingyuan [1 ]
Ling, Yong [2 ]
机构
[1] Nantong Univ, Coll Chem & Chem Engn, Nantong 226019, Peoples R China
[2] Nantong Univ, Sch Pharm, Nantong 226001, Peoples R China
基金
中国国家自然科学基金;
关键词
oxazole; cyanoacrylate; synthesis; herbicidal activity; BIOLOGICAL-ACTIVITIES; 2-CYANOACRYLATES; BIOACTIVITY; DESIGN;
D O I
10.6023/cjoc201802026
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In search of novel cyanoacrylates with potent bioactivity, a series of new cyanoacrylate derivatives containing substituted oxazole moiety were designed and synthesized through the strategy of active substructure combination. They were structurally characterized by H-1 NMR, C-13 NMR and elemental analysis. Preliminary bioassay data showed that most title compounds possessed good herbicidal activity at the dosage of 1500 g/ha, 9 compounds exhibited herbicidal activity against Brassica juncea with 80%similar to 100%, 12 compounds had herbicidal activity against Chenopodium serotinum L. with 80%similar to 100%, two compounds both displayed 70% herbicidal activity against Alopecurus aequalis Sobol, and one compound showed 100%, 70%, and 60% herbicidal activity against Rumex acetosa L., Polypogon fugax Nees ex Steud and Poa acroleuca Steud, respectively. Additionally, the inhibitory rates of one compound against Brassica juncea and Rumex acetosa L. were both 30% at 37.5 g/ha.
引用
收藏
页码:1772 / 1778
页数:7
相关论文
共 24 条
[1]   Synthesis and Herbicidal Activity of Novel Cyanoacrylates Containing Substituted Pyridyl Moiety [J].
Dai, Hong ;
Chen, Jia ;
Hong, Yu ;
Yuan, Binying ;
Chen, Yumeng ;
Shi, Yujun ;
Ma, Ruiyuan ;
Liang, Zhipeng ;
Shi, Jian .
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2017, 37 (03) :739-745
[2]   Synthesis and Herbicidal Activities of Novel Cyanoacrylate Derivatives Containing Substituted Pyrimidine Moiety [J].
Dai, Hong ;
Fang, Yuan ;
Li, Yang ;
Wang, Xianglong ;
Xiang, Xingbang ;
Ge, Shushan ;
Shi, Yujun .
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2016, 36 (12) :2973-2980
[3]   The thiazoylmethoxy modification on pyrazole oximes: Synthesis and insecticidal biological evaluation beyond acaricidal activity [J].
Dai, Hong ;
Xiao, Yan-Shuang ;
Li, Zhong ;
Xu, Xiao-Yong ;
Qian, Xu-Hong .
CHINESE CHEMICAL LETTERS, 2014, 25 (07) :1014-1016
[4]   Antimycobacterial natural products: synthesis and preliminary biological evaluation of the oxazole-containing alkaloid texaline [J].
Giddens, AC ;
Boshoff, HIM ;
Franzblau, SG ;
Barry, CE ;
Copp, BR .
TETRAHEDRON LETTERS, 2005, 46 (43) :7355-7357
[5]   Evolution of toxicity upon hydrolysis of fenoxaprop-p-ethyl [J].
Lin, Jing ;
Chen, Jingwen ;
Cai, Xiyun ;
Qlao, Xianliang ;
Huang, Liping ;
Wang, Degao ;
Wang, Zhuang .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2007, 55 (18) :7626-7629
[6]  
Liu HY, 2000, CHEM J CHINESE U, V21, P1855
[7]   Synthesis, crystal structure, and biological activities of 2-cyanoacrylates containing furan or tetrahydrofuran moieties [J].
Liu, Yuxiu ;
Cai, Baoli ;
Li, Yonghong ;
Song, Haibin ;
Huang, Runqiu ;
Wang, Qingmin .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2007, 55 (08) :3011-3017
[8]   Optimization of anti-proliferative activity using a screening approach with a series of bis-heterocyclic G-quadruplex ligands [J].
Ohnmacht, Stephan A. ;
Ciancimino, Cristina ;
Vignaroli, Giulia ;
Gunaratnam, Mekala ;
Neidle, Stephen .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (19) :5351-5355
[9]   A novel synthesis of (E)-3-methylthio-3-substituted arylamino-2-cyanoacrylates under microwave irradiation [J].
Ouyang, G ;
Song, B ;
Zhang, HP ;
Yang, S ;
Jin, LH ;
Li, QZ ;
Hu, DY .
MOLECULES, 2005, 10 (10) :1351-1357
[10]   Synthesis and antimicrobial activity of amine linked bis- and tris-heterocycles [J].
Prakash, T. Bhanu ;
Reddy, G. Dinneswara ;
Padmaja, A. ;
Padmavathi, V. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 82 :347-354