Synthesis and Nematicidal Activities of 8-Azabicyclo[3.2.1]-octane-3-isoxazole Oxime Derivatives

被引：6

作者：

Lu, Qing ^{[1
]}

Shen, Qiaoying ^{[1
]}

Sun, Lu ^{[1
]}

Wang, Jiayi ^{[1
]}

Song, Gonghua ^{[1
]}

机构：

[1] E China Univ Sci & Technol, Sch Pharm, Shanghai Key Lab Chem Biol, Shanghai 200237, Peoples R China

来源：

CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 36卷 / 04期

基金：

中国国家自然科学基金;

关键词：

8-azabicyclo; nematicide; serotonin; 1,3-dipolar cycloaddition reaction; ANTAGONISTS; SEROTONIN;

D O I：

10.6023/cjoc201601036

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Based on the potential nematicidal activities of tropane derivatives structure, 19 unreported 8-azabicyclo[3.2.1]-octane-3-isoxazole oxime derivatives were designed and synthesized by 1,3-dipolar cycloaddition reaction. Their structures were confirmed by H-1 NMR, C-13 NMR and HRMS techniques. Preliminary bioassay results showed that targeted compounds exhibited good nematicidal activities against Meloidogyne incognita at concentration of 25 mg/L, and 8-methyl-8-azabicyclo-[3.2.1]octan-3-one-O-((3-(4-nitrophenyl)-4,5-dihydroisoxazol-5-yl)methyl)oxime (9e) showed the best nematicidal activities with 55.6% at concentration of 1 mg/L.

引用

页码：760 / 767

页数：8

共 28 条

[1] Arnot LF, 2011, J S AFR VET ASSOC, V82, P232
[2] Strategies for transgenic nematode control in developed and developing world crops
Atkinson, Howard J.
Lilley, Catherine J.
Urwin, Peter E.
[J]. CURRENT OPINION IN BIOTECHNOLOGY, 2012, 23 (02) : 251 - 256
[3] Design and Synthesis of Novel Insecticides Based on the Serotonergic Ligand 1-[(4-Aminophenyl)ethyl]-4-[3-(trifluoromethyl)phenyl]piperazine (PAPP)
Cai, Mingyi
Zhong Li
Feng Fan
Huang, Qingchun
Shao, Xusheng
Song, Gonghua
[J]. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2010, 58 (05) : 2624 - 2629
[4] HE HW, 2000, PESTICIDE, V8, P4
[5] CONFORMATION-ACTIVITY RELATIONSHIP STUDY OF 5-HT3 RECEPTOR ANTAGONISTS AND A DEFINITION OF A MODEL FOR THIS RECEPTOR-SITE
HIBERT, MF
HOFFMANN, R
MILLER, RC
CARR, AA
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (06) : 1594 - 1600
[6] Fluensulfone is a nematicide with a mode of action distinct from anticholinesterases and macrocyclic lactones
Kearn, James
Ludlow, Elizabeth
Dillon, James
O'Connor, Vincent
Holden-Dye, Lindy
[J]. PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY, 2014, 109 : 44 - 57
[7] Rearrangement of allyl groups in dyad systems - Amine oxides
Kleinschmidt, RF
Cope, AC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1944, 66 : 1929 - 1933
[8] KOYAMA J, 1983, CHEM PHARM BULL, V31, P2601
[9] A neurohormonal role for serotonin in the control of locust oviducts
Lange, AB
[J]. ARCHIVES OF INSECT BIOCHEMISTRY AND PHYSIOLOGY, 2004, 56 (04) : 179 - 190
[10] Li M. Q., 2001, CHEM REAG, V23, P271

← 1 2 3 →