Microwave-assistant Syntheses, Crystal Structures and Safener Activities of Two Substituted Phenyl Isoxazole Derivatives

摘要
图/表
参考文献
相关文章 (13)

全文: PDF (731 KB) HTML (1 KB)
输出: BibTeX | EndNote (RIS)

摘要 Two novel substituted phenyl isoxazole benzoxazine formamide derivatives were designed and synthesized with substituted o-aminophenol, 1,2-dibromoethane and different phenyl substituted isoxazole formyl chloride as the raw materials via microwave assistant synthesis. The target compounds were characterized by IR, 1H NMR, 13C NMR and HRMS. Both single-crystal structures were further determined by X-ray diffraction. 3-(2΄-Chloro-6΄-fluoro-phenyl)-4-(2΄,3΄-dihydro-1΄,4΄-benzoxazine)-5-methyl-isoxazole formamide (4a) crystallizes in orthorhombic system, P21 space group with a = 8.9414(18), b = 10.834(2), c = 17.706(4) Å, V = 1715.1(6) Å3, Dc = 1.444 Mg/m3, Z = 4, F(000) = 768, (MoK) = 0.255 mm-1, R = 0.0406 and wR = 0.1171. 3-Phenyl-4-(6- methyl-2΄,3΄-dihydro-1΄,4΄-benzoxazine)-5-methyl-isoxazole formamide (4b) is of triclinic system, space group P with a = 7.7659(16), b = 8.3626(17), c = 13.484(3) Å,  = 76.04(3)°,  = 100.63(3)°,  = 82.01(3)°, V = 841.6(3) Å3, Dc = 1.319 Mg/m3, Z = 2, F(000) = 352, (MoK) = 0.090 mm-1, R = 0.0672 and wR = 0.2671. Both crystals are packed through C–H···O hydrogen bonding interaction. There is C–H···F hydrogen bond between 4a molecules, and C–H···N between 4b molecules. Bioassay results showed that compounds 4a and 4b exhibited detoxification on maize and restored maize growth index.

	服务

	把本文推荐给朋友
	加入我的书架
	加入引用管理器
	E-mail Alert
	RSS
	作者相关文章
	高颖超
	邵鑫鑫
	付颖

关键词 ： isoxazole benzoxazine formamide, microwave-assistant synthesis, single-crystal structure, safener activity

Abstract：Two novel substituted phenyl isoxazole benzoxazine formamide derivatives were designed and synthesized with substituted o-aminophenol, 1,2-dibromoethane and different phenyl substituted isoxazole formyl chloride as the raw materials via microwave assistant synthesis. The target compounds were characterized by IR, 1H NMR, 13C NMR and HRMS. Both single-crystal structures were further determined by X-ray diffraction. 3-(2΄-Chloro-6΄-fluoro-phenyl)-4-(2΄,3΄-dihydro-1΄,4΄-benzoxazine)-5-methyl-isoxazole formamide (4a) crystallizes in orthorhombic system, P21 space group with a = 8.9414(18), b = 10.834(2), c = 17.706(4) Å, V = 1715.1(6) Å3, Dc = 1.444 Mg/m3, Z = 4, F(000) = 768, (MoK) = 0.255 mm-1, R = 0.0406 and wR = 0.1171. 3-Phenyl-4-(6- methyl-2΄,3΄-dihydro-1΄,4΄-benzoxazine)-5-methyl-isoxazole formamide (4b) is of triclinic system, space group P with a = 7.7659(16), b = 8.3626(17), c = 13.484(3) Å,  = 76.04(3)°,  = 100.63(3)°,  = 82.01(3)°, V = 841.6(3) Å3, Dc = 1.319 Mg/m3, Z = 2, F(000) = 352, (MoK) = 0.090 mm-1, R = 0.0672 and wR = 0.2671. Both crystals are packed through C–H···O hydrogen bonding interaction. There is C–H···F hydrogen bond between 4a molecules, and C–H···N between 4b molecules. Bioassay results showed that compounds 4a and 4b exhibited detoxification on maize and restored maize growth index.

Key words： isoxazole benzoxazine formamide microwave-assistant synthesis single-crystal structure safener activity

收稿日期: 2021-02-22 出版日期: 2021-09-09

基金资助:This work was supported by the National Natural Science Foundation of China (No. 31801784 and 31572042) and Undergraduate SIPT program of Northeast Agricultural University (No. 202010224112)

通讯作者: fuying@neau.edu.cn E-mail: fuying@neau.edu.cn

引用本文:

高颖超;邵鑫鑫;付颖. Microwave-assistant Syntheses, Crystal Structures and Safener Activities of Two Substituted Phenyl Isoxazole Derivatives[J]. 结构化学, 2021, 40(9): 1231-1237.
GAO Ying-Chao;SHAO Xin-Xin;FU Ying. Microwave-assistant Syntheses, Crystal Structures and Safener Activities of Two Substituted Phenyl Isoxazole Derivatives. CHINESE JOURNAL OF STRUCTURAL CHEMISTRY, 2021, 40(9): 1231-1237.

链接本文:

http://manu30.magtech.com.cn/jghx/CN/ 或 http://manu30.magtech.com.cn/jghx/CN/Y2021/V40/I9/1231

REFERENCES
(1) Green, J. M.; Hazel, C. B.; Forney, D. R.; Pugh, L. M. New multiple-herbicide crop resistance and formulation technology to augment the utility of glyphosate. Pest Manag. Sci. 2008, 64, 332339.
(2) Riechers, D. E.; Kreuz, K.; Zhang, Q. Detoxification without intoxication: herbicide safeners activate plant defense gene expression. Plant Physiol. 2010, 153, 313.
(3) Ye, F.; Zhai, Y.; Guo, K. L.; Liu, Y. X.; Li, N.; Gao, S.; Zhao, L. X.; Fu, Y. Safeners improve maize tolerance under herbicide toxicity stress by increasing the activity of enzymes in vivo. J. Agric. Food Chem. 2019, 6, 1156811576.
(4) John, D. S.; Hansjoachim, L.; Christopher, J. S.; Allison, N. R.; David, M. C. Environmental fate and effects of dichloroacetamide herbicide safeners: “inert” yet biologically active agrochemical ingredients. Environ. Sci. Technol. Lett. 2015, 2, 260269.
(5) Lucini, L.; Molinari, G. P. Detection of the herbicide fenoxaprop-P-ethyl, its agronomic safener isoxadifen ethyl and their metabolites residue in rice. Qual. Assur. Saf. Crop. Foods 2011, 3, 6368.
(6) Davies, J.; Caseley, J. C. Herbicide safeners: a review. J. Pestic. Sci. 1999, 55, 10431058.
(7) Sun, L. L.; Xu, H. L.; Su, W. C.; Xue, F.; An, S. H.; Lu, C. T.; Wu, R. H. The 633 expression of detoxification genes in two maize cultivars by interaction of 634 isoxadifen-ethyl and nicosulfuron. Plant Physiol. Bioch. 2018, 129, 101108.
(8) Lucini, L.; Molinari, G. P. Residues of the herbicide fenoxaprop-P-ethyl, its agronomic safener isoxadifen-ethyl and their metabolites in rice after field application. Pest Manag. Sci. 2010, 66, 621626.
(9) Behringer, C.; Bartsch, K.; Schaller, A. Safeners recruit multiple signaling pathways for the orchestrated induction of the cellular xenobiotic detoxification machinery in Arabidopsis. Plant Cell Environ. 2011, 34, 19701985.
(10) Ilas, J.; Anderluh, P. S.; Dolenc, M. S. Recent advances in the synthesis of 2H-1,4-benzoxazin-3-(4H)-ones and 3,4-dihydro-2H-1,4-benzoxazines. J. Cheminformatics 2005, 61, 73257348.
(11) Feng, G.; Wu, J.; Dai, W. M. One-pot regioselective annulation toward 3,4-dihydro-3-oxo-2H-1,4-benzoxazine scaffolds under controlled microwave heating. Tetrahedron 2006, 62, 46354642.
(12) Zhang, Y. Y.; Gao, S.; Liu, Y. X.; Wang, C.; Jiang, W.; Zhao, L. X.; Fu, Y.; Ye, F. Design, synthesis, and biological activity of novel diazabicyclo derivatives as safeners. J. Agric. Food Chem. 2020, 68, 34033414.
(13) Fu, Y.; Zhang, S. Q.; Liu, Y. X.; Wang, J. Y.; Gao, S.; Zhao, L. X.; Ye, F. Design, synthesis, SAR and molecular docking of novel green niacin-triketone HPPD inhibitor. Ind. Crop. Prod. 2019, 137, 566575.
(14) Fu, Y.; Zhang, D.; Kang, T.; Guo, Y. Y.; Chen, W. G.; Gao, S.; Ye, F. Fragment splicing-based design, synthesis and safener activity of novel substituted phenyl oxazole derivatives. Bioorg. Med. Chem. Lett. 2019, 29, 570576.
(15) Guo, K. L.; Zhao, L. X.; Wang, Z. W.; Gao, Y. C.; Li, J. J.; Gao, S.; Fu, Y.; Ye, F. Design, synthesis, and bioevaluation of substituted phenyl isoxazole analogues as herbicide safeners. J. Agric. Food Chem. 2020, 68, 1055010559.
(16) Fu, Y.; Wang, M.; Zhao, L. X.; Zhang, S. Q., Liu, Y. X.; Guo, Y. Y.; Zhang, D.; Gao, S.; Ye, F. Design, synthesis, herbicidal activity and CoMFA of novel aryl-formyl piperidinone HPPD inhibitors. Pestic. Biochem. Phys. 2021, 171, 10481123.
(17) Gao, S.; Liu, Y. Y.; Jiang, J. Y.; Li, X. M.; Zhao, L. X.; Fu, Y.; Ye, F. Encapsulation of thiabendazole in hydroxypropyl--cyclodextrin nanoﬁbers via polymer-free electrospinning and its characterization. Pest Manag. Sci. 2020, 76, 32643272.
(18) Li, L.; Gao, S.; Liu, Y.; Liu, Y. L.; Li, P.; Ye, F.; Fu, Y. Cobalt(II) complex as a fluorescent sensing platform for the selective and sensitive detection of triketone HPPD inhibitors. J. Hazard. Mater. 2021, 404, 12401510.
(19) Fu, Y.; Wang, K.; Wang, P.; Kang, J. X.; Gao, S.; Zhao, L. X.; Ye, F. Design, synthesis and herbicidal activity evaluation of novel aryl-naphthyl methanone derivatives. Front. Chem. 2019, 7, 210.
(20) Liu, X. H.; Zhai, Z. W.; Xu, X. Y.; Yang, M. Y.; Sun, Z. H.; Weng, J. Q.; Tan, C. X.; Chen, J. Facile and efficient synthesis and herbicidal activity determination of novel 1,2,4-triazolo[4,3-a]pyridin-3(2H)-one derivatives via microwave irradiation. Bioorg. Med. Chem. Lett. 2015, 25, 55245528.
(21) Mu, J. X.; Yang, M. Y.; Sun, Z. H.; Tan, C. X.; Weng, J. Q.; Wu, H. K.; Liu, X. H. Synthesis, crystal structure and DFT studies of 8-chloro-3-((3-chlorobenzyl)thio)-[1,2,4]triazolo[4,3-a]pyridine. Crystals 2015, 5, 491500.
(22) Fu, Y.; Zhang, D.; Zhang, S. Q.; Liu, Y. X.; Guo, Y. Y.; Wang, M. X.; Gao, S.; Zhao, L. X.; Ye, F. Discovery of N-aroyl diketone/triketone derivatives as novel 4-hydroxyphenylpyruvatedioxygenase inhibiting-based herbicides. J. Agric. Food Chem. 2019, 67, 1183911847.
(23) Ye, F.; Zhai, Y.; Kang, T.; Wu, S. L.; Li, J. J.; Gao, S.; Zhao, L. J.; Fu, Y. Rational design, synthesis and structure-activity relationship of novel substituted oxazole isoxazole carboxamides as herbicide safener. Pestic. Biochem. Phys. 2019, 157, 6068.
(24) Zhang, Y. Y.; Gao, S.; Hoang, M. T.; Wang, Z. W.; Ma, X.; Zhai, Y.; Li, N.; Zhao, L. X.; Fu, Y.; Ye, F. Protective efficacy of phenoxyacetyl oxazolidine derivatives as safeners against nicosulfuron toxicity in maize. Pest Manag. Sci. 2021, 77, 177183.
(25) Thomann, A.; Eberhard, J.; Allegretta, G.; Empting, M.; Hartmann, R. W. Mild and catalyst-free microwave-assisted synthesis of 4,6-disubstituted 2-methylthiopyrimidines-exploiting tetrazole as an efficient leaving group. Synlett. 2015, 26, 26062610.
(26) Sheldrick, G. M. SHELXS-97, Program for X-ray Crystal Structure Solution. University of Göttingen, Göttingen, Germany 1997.
(27) Sheldrick, G. M. SHELXL-97, Program for X-ray Crystal Structure Refinement. University of Göttingen, Göttingen, Germany 1997.
(28) Scarponi, L.; Buono, D. D. Benoxacor induction of terbuthylazine detoxification in Zea mays and festuca arundinacea. J. Agric. Food Chem. 2005, 53, 24832488.
(29) Kang, T.; Liu, C. G.; Wu, S. L.; Gao, S.; Ye, F.; Fu, Y. Microwave assistant synthesis and crystal structure of two substituted oxazole isoxazole carboxamides. Chin. J. Struct. Chem. 2020, 39, 19061911.
(30) Swamy, G. Y.; Ravikumar, K.; Ramakrishna, K. V. Synthesis and crystal structure of bis[2-(4-methylphenyl)-1-phenethyl-4(1H)-quinazolinone] dichlorocopper(II). Polyhedron 2013, 49, 145150.
(31) Wang, Z. W.; Zhao, L. X.; Ma, P.; Ye, T.; Fu, Y.; Ye, F. Fragments recombination, design, synthesis, safener activity and QASR of novel substituted dichloroacetylphenyl sulfonamide derivatives. Pest Manag. Sci. 2021, 77, 17241738.
(32) Kang, T.; Gao, S.; Zhao, L. X.; Zhai, Y.; Ye, F.; Fu, Y. Design, synthesis and SAR of novel 1,3-disubstituted imidazolidine or hexahydropyrimidine derivatives as herbicide safeners. J. Agric. Food Chem. 2021, 69, 4554.
(33) Gao, S.; Jiang, J. Y.; Li, X. M.; Liu, Y. Y.; Zhao, L. X.; Fu, Y.; Ye, F. Enhanced physicochemical properties and herbicidal activity of an environment-friendly clathrate formed by -cyclodextrin and herbicide cyanazine. J. Mol. Liq. 2020, 305, 1128588.