Design, Synthesis and Evaluation of Novel Isoxazolines/Oxime Sulfonates of 2'(2',6')-(Di)Chloropodophyllotoxins as Insecticidal Agents.
A series of 2'(2',6')-(di)halogeno-isoxazolopodophyllic acids-based esters, and oxime sulfonates of 2'(2',6')-(di)halogenopodophyllones were prepared by structural modifications of podophyllotoxin as insecticidal agents against Mythimna separata Walker. It was found that when 2'(2',6')-(di)halogenopodophyllones or 2'(2',6')-(di)chloropicropodophyllones reacted with hydroxylamine hydrochloride, the desired products were related with the configuration of their lactones. Three key single-crystal structures of Ie, IIe and IIIb were determined by X-ray diffraction. Especially compounds IIc and Vc showed the highest insecticidal activity. Moreover, some interesting results of structure-insecticidal activity relationships of tested compounds were also observed.
Research Institute of Pesticidal Design &Synthesis, College of Sciences, Northwest A&F University, Yangling 712100, Shaanxi Province, P. R. China.
Mingqiao
M
Yu
Research Institute of Pesticidal Design &Synthesis, College of Sciences, Northwest A&F University, Yangling 712100, Shaanxi Province, P. R. China.
Guangci
G
Liu
Research Institute of Pesticidal Design &Synthesis, College of Sciences, Northwest A&F University, Yangling 712100, Shaanxi Province, P. R. China.
Yuanyuan
Y
Zhang
Research Institute of Pesticidal Design &Synthesis, College of Sciences, Northwest A&F University, Yangling 712100, Shaanxi Province, P. R. China.
Tao
T
Feng
Research Institute of Pesticidal Design &Synthesis, College of Sciences, Northwest A&F University, Yangling 712100, Shaanxi Province, P. R. China.
Ming
M
Xu
Research Institute of Pesticidal Design &Synthesis, College of Sciences, Northwest A&F University, Yangling 712100, Shaanxi Province, P. R. China.|Shaanxi Key Laboratory of Natural Products &Chemical Biology, College of Plant Protection, Northwest A&F University, Yangling 712100, Shaanxi Province, P. R. China.
Hui
H
Xu
Bioorg Med Chem Lett. 2014 Nov 15;24(22):5228-33
25442317
Bioorg Med Chem Lett. 2010 Aug 1;20(15):4503-6
20584606
J Agric Food Chem. 2015 Aug 5;63(30):6668-74
26166302
Sci Rep. 2016 Apr 20;6:24652
27095599
Pest Manag Sci. 2016 Apr;72 (4):707-18
25989043
J Agric Food Chem. 2012 Aug 29;60(34):8435-43
22891988
J Econ Entomol. 2016 Apr;109(2):832-6
26709293
Bioorg Med Chem Lett. 2015 Oct 1;25(19):4239-44
26292628
Bioorg Med Chem Lett. 2014 Dec 15;24(24):5627-9
25466187
J Agric Food Chem. 2016 Feb 3;64(4):840-51
26807485
Bioorg Med Chem Lett. 2013 Oct 15;23(20):5592-8
24018192
J Agric Food Chem. 2015 Oct 14;63(40):8787-92
26395226
Mini Rev Med Chem. 2011 Sep;11(10):901-9
21781026
Mitochondrial DNA. 2015;26(6):881-2
24409861
Bioorg Med Chem Lett. 2015 Nov 15;25(22):5025-7
26497285
J Med Chem. 1992 Mar 6;35(5):866-71
1312600
J Agric Food Chem. 2015 Apr 29;63(16):4042-9
25853587
J Agric Food Chem. 2016 Jan 27;64(3):552-62
26728549
J Agric Food Chem. 2015 Mar 4;63(8):2206-14
25619118
J Agric Food Chem. 2014 Apr 30;62(17):3726-33
24724803
J Agric Food Chem. 2013 Aug 28;61(34):8148-55
23915199
Sci Rep. 2016 Mar 22;6:23355
27003579
Angew Chem Int Ed Engl. 2014 Mar 17;53(12):3115-9
24519950
J Org Chem. 2013 Apr 5;78(7):3250-61
23496308
J Agric Food Chem. 2014 Dec 3;62(48):11613-9
25406111
Sci Rep. 2015 Aug 13;5:13077
26268805