Synthesis, Characterization, X-ray Crystal Structure and Herbicidal Activity of (E)-2-(2,4-Dichlorophenoxy)-1- (5,5-dimethyl-2-oxido-1,3,2-dioxaphosphinan-2-yl)vinyl 2-(2,4-Dichlorophenoxy)acetate
English
Synthesis, Characterization, X-ray Crystal Structure and Herbicidal Activity of (E)-2-(2,4-Dichlorophenoxy)-1- (5,5-dimethyl-2-oxido-1,3,2-dioxaphosphinan-2-yl)vinyl 2-(2,4-Dichlorophenoxy)acetate
-
Key words:
- X-ray crystallography
- / phosphonate
- / (E)-vinyl acetate
- / herbicidal activity
-
-
-
[1]
(1) Phillips, A. M. F.; Barros, M. T.; Pacheco, M.; Dias, R. Synthesis and biological evaluation of α-hydroxyalkylphosphonates as new antimicrobial agents. Bioorg. Med. Chem. Lett. 2014, 24, 49-53.(1) Phillips, A. M. F.; Barros, M. T.; Pacheco, M.; Dias, R. Synthesis and biological evaluation of α-hydroxyalkylphosphonates as new antimicrobial agents. Bioorg. Med. Chem. Lett. 2014, 24, 49-53.
-
[2]
(2) Roy, N. K.; Nidiry, E. S. J.; Vasu, K.; Bedi, S.; Lalljee, B.; Singh, B. Quantitative structure-activity relationship studies of O,O-bisaryl alkylphosphonate fungicides by Hansch approach and principal component analysis. J. Agric. Food Chem. 1996, 44, 3971-3976.(2) Roy, N. K.; Nidiry, E. S. J.; Vasu, K.; Bedi, S.; Lalljee, B.; Singh, B. Quantitative structure-activity relationship studies of O,O-bisaryl alkylphosphonate fungicides by Hansch approach and principal component analysis. J. Agric. Food Chem. 1996, 44, 3971-3976.
-
[3]
(3) Gosset, G.; Clement, J. L.; Culcasi, M. Cydepmpos: a class of stable cyclic DEPMPO derivatives with improved properties as mechanistic market of stereoselective hydroxyl radical adduct formation in biological systems. Bioorg. Med. Chem. 2011, 19, 2218-2230.(3) Gosset, G.; Clement, J. L.; Culcasi, M. Cydepmpos: a class of stable cyclic DEPMPO derivatives with improved properties as mechanistic market of stereoselective hydroxyl radical adduct formation in biological systems. Bioorg. Med. Chem. 2011, 19, 2218-2230.
-
[4]
(4) Kiran, Y. B.; Reddy, C. D.; Gunasekar, D.; Reddy, C. S.; Leon, A.; Barbosa, L. C. A. Synthesis and anticancer activity of new class of bisphosphonates/phosphanamidates. Eur. J. Med. Chem. 2008, 43, 885-892.(4) Kiran, Y. B.; Reddy, C. D.; Gunasekar, D.; Reddy, C. S.; Leon, A.; Barbosa, L. C. A. Synthesis and anticancer activity of new class of bisphosphonates/phosphanamidates. Eur. J. Med. Chem. 2008, 43, 885-892.
-
[5]
(5) Xie, B.; Wang, Y. M.; Zou, L. K.; Wang, J.; Li, Y. L.; Lin, X. 2,2'-Bipyridine adduct of bis(O,O'-di(2-phenylethyl)dithiophosphato)cadmium(II): synthesis, spectroscopic characterization, crystal structure and antibacterial activity. Chin. J. Struct. Chem. 2013, 32, 1457-1464.(5) Xie, B.; Wang, Y. M.; Zou, L. K.; Wang, J.; Li, Y. L.; Lin, X. 2,2'-Bipyridine adduct of bis(O,O'-di(2-phenylethyl)dithiophosphato)cadmium(II): synthesis, spectroscopic characterization, crystal structure and antibacterial activity. Chin. J. Struct. Chem. 2013, 32, 1457-1464.
-
[6]
(6) Zhang, X. L.; Zou, L. K.; Xie, B.; Lai, C.; Li, Y. L. Synthesis and crystal structure of bis[O,O'-bis(4-tert-butylphenyl)dithiophosphate]nickyl(II). Chin. J. Struct. Chem. 2013, 32, 779-785.(6) Zhang, X. L.; Zou, L. K.; Xie, B.; Lai, C.; Li, Y. L. Synthesis and crystal structure of bis[O,O'-bis(4-tert-butylphenyl)dithiophosphate]nickyl(II). Chin. J. Struct. Chem. 2013, 32, 779-785.
-
[7]
(7) Patrone, J. D.; Yao, J. W.; Scott, N. E.; Dotson, G. D. Selective inhibitors of bacterial phosphopantothenoylcysteine synthetase. J. Am. Chem. Soc. 2009, 131, 16340-16341.(7) Patrone, J. D.; Yao, J. W.; Scott, N. E.; Dotson, G. D. Selective inhibitors of bacterial phosphopantothenoylcysteine synthetase. J. Am. Chem. Soc. 2009, 131, 16340-16341.
-
[8]
(8) Huttunen, K. M.; Risto, O, N. T.; Raunio, J. H.; Rautio, J. Design, synthesis, and evaluation of novel cyclic phosphates of 5-aminosalicylic acid as cytochrome P450-activated prodrugs. Mol. Pharm. 2013, 10, 532-537.(8) Huttunen, K. M.; Risto, O, N. T.; Raunio, J. H.; Rautio, J. Design, synthesis, and evaluation of novel cyclic phosphates of 5-aminosalicylic acid as cytochrome P450-activated prodrugs. Mol. Pharm. 2013, 10, 532-537.
-
[9]
(9) Baillie, A. C.; Wright, K.; Wright, B. J.; Earnshaw, C. G. Inhibitors of pyruvate dehydrogenase as herbicides. Pestic. Biochem. Physiol. 1988, 30, 103-112.(9) Baillie, A. C.; Wright, K.; Wright, B. J.; Earnshaw, C. G. Inhibitors of pyruvate dehydrogenase as herbicides. Pestic. Biochem. Physiol. 1988, 30, 103-112.
-
[10]
(10) Wang, W.; He, H. W.; Zuo, N.; He, H. F.; Peng, H.; Tan, X. S. Synthesis and herbicidal activity of 2-(substituted phenoxyacetoxy)alkyl-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one. J. Agric. Food Chem. 2012, 60, 7581-7587.(10) Wang, W.; He, H. W.; Zuo, N.; He, H. F.; Peng, H.; Tan, X. S. Synthesis and herbicidal activity of 2-(substituted phenoxyacetoxy)alkyl-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one. J. Agric. Food Chem. 2012, 60, 7581-7587.
-
[11]
(11) Wang, W.; He, H. W.; Zuo, N.; Zhang, X.; Lin, J. S.; Chen, W.; Peng, H. Synthesis and herbicidal activity of 2-(substituted phenoxyacetoxy)alkyl-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one containing fluorine. J. Fluor. Chem. 2012, 142, 24-28.(11) Wang, W.; He, H. W.; Zuo, N.; Zhang, X.; Lin, J. S.; Chen, W.; Peng, H. Synthesis and herbicidal activity of 2-(substituted phenoxyacetoxy)alkyl-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one containing fluorine. J. Fluor. Chem. 2012, 142, 24-28.
-
[12]
(12) He, H. W.; Wang, W.; Zuo, N.; Sheng, X. J.; Peng, H.; Tan, X. S. Substituted phenoxyethyl (isopropyl) acyloxyalkyl phosphonate comprising phosphorusheterocyclic ring and having herbicidal activity, and preparation therefor. US Patent. 171644. 2014.(12) He, H. W.; Wang, W.; Zuo, N.; Sheng, X. J.; Peng, H.; Tan, X. S. Substituted phenoxyethyl (isopropyl) acyloxyalkyl phosphonate comprising phosphorusheterocyclic ring and having herbicidal activity, and preparation therefor. US Patent. 171644. 2014.
-
[13]
(13) You, G. Y.; Cheng, Z. Q.; Peng, H.; He, H. W. The synthesis and characterization of a novel phosphorus-nitrogen containing flame retardant and its application in epoxy resins. J. Appl. Polym. Sci. 2014, 131, 1-8.(13) You, G. Y.; Cheng, Z. Q.; Peng, H.; He, H. W. The synthesis and characterization of a novel phosphorus-nitrogen containing flame retardant and its application in epoxy resins. J. Appl. Polym. Sci. 2014, 131, 1-8.
-
[14]
(14) Wei, T. B.; Zhang, Y. M.; Xing, H. Y. Phase transfer catalyzed synthesis of amides and esters of 2,4-dichlorophenoxyacetic acid. Synth. Commun. 2000, 30, 485-491.(14) Wei, T. B.; Zhang, Y. M.; Xing, H. Y. Phase transfer catalyzed synthesis of amides and esters of 2,4-dichlorophenoxyacetic acid. Synth. Commun. 2000, 30, 485-491.
-
[15]
(15) Wang, T.; Wang, W.; Peng, H.; He, H. W. Synthesis and biological activity of 1-(substituted phenoxyacetoxy)-1-(pyridine-2-yl or thien-2-yl)methylphosphonates. J. Heterocycl. Chem. 2015, 52, 173-179.(15) Wang, T.; Wang, W.; Peng, H.; He, H. W. Synthesis and biological activity of 1-(substituted phenoxyacetoxy)-1-(pyridine-2-yl or thien-2-yl)methylphosphonates. J. Heterocycl. Chem. 2015, 52, 173-179.
-
[16]
(16) Zhang, M.; Zou, J. P.; Zeng, R. S.; Zhang, Y. Synthesis and molecular structure of (E)-1-(morpholino)-2-(thiomethyl)-2-phenylvinylphosphonate. Chin. J. Struct. Chem. 2005, 24, 201-203.(16) Zhang, M.; Zou, J. P.; Zeng, R. S.; Zhang, Y. Synthesis and molecular structure of (E)-1-(morpholino)-2-(thiomethyl)-2-phenylvinylphosphonate. Chin. J. Struct. Chem. 2005, 24, 201-203.
-
[17]
(17) Xue, S. J.; Xiang, C. S.; Yu, S. R.; Sun, J. F.; Chai, A.; Shen, J. Synthesis and crystal structure of 5-(p-tolyl)-4-[2-(2,4-dichlorophenoxy)acetamido]-1,2,4-triazole-3-thione ethyl acetate solvate. Chin. J. Struct. Chem. 2008, 27, 389-393.(17) Xue, S. J.; Xiang, C. S.; Yu, S. R.; Sun, J. F.; Chai, A.; Shen, J. Synthesis and crystal structure of 5-(p-tolyl)-4-[2-(2,4-dichlorophenoxy)acetamido]-1,2,4-triazole-3-thione ethyl acetate solvate. Chin. J. Struct. Chem. 2008, 27, 389-393.
-
[18]
(18) Liu, Y.; Wei, J.; Shi, D. Q.; Wang, C. G. Synthesis and crystal structure of cis 2-(6-chloro-3-pyridylmethylamino)-4-chlorophenyl-5,5-dimethyl- 1,3,2-dioxaphosphinane 2-oxides. Chin. J. Struct. Chem. 2005, 24, 196-200.(18) Liu, Y.; Wei, J.; Shi, D. Q.; Wang, C. G. Synthesis and crystal structure of cis 2-(6-chloro-3-pyridylmethylamino)-4-chlorophenyl-5,5-dimethyl- 1,3,2-dioxaphosphinane 2-oxides. Chin. J. Struct. Chem. 2005, 24, 196-200.
-
[19]
(19) Zuo, N.; He, H. W. 2-{(2-Chlorophenyl)[(2,4-dichlorophenoxy)acetoxy]methyl}-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one. Acta. Cryst. E 2007, 63, 794-795.(19) Zuo, N.; He, H. W. 2-{(2-Chlorophenyl)[(2,4-dichlorophenoxy)acetoxy]methyl}-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one. Acta. Cryst. E 2007, 63, 794-795.
-
[20]
(20) Ning, L. H.; Peng, H.; He, H. W. Synthesis, characterization and X-ray crystal structure of O,O'-dipropyl α-(2,4-dichlorolphenoxyacylamido)- α-(4-methoxyphenyl) methylphosphonates. Chin. J. Struct. Chem. 2013, 32, 1392-1396.(20) Ning, L. H.; Peng, H.; He, H. W. Synthesis, characterization and X-ray crystal structure of O,O'-dipropyl α-(2,4-dichlorolphenoxyacylamido)- α-(4-methoxyphenyl) methylphosphonates. Chin. J. Struct. Chem. 2013, 32, 1392-1396.
-
[21]
(21) Robin, T.; Olga, K. Hydrogen-bond geometry in organic crystals. Acc. Chem. Res. 1984, 17, 320-326.(21) Robin, T.; Olga, K. Hydrogen-bond geometry in organic crystals. Acc. Chem. Res. 1984, 17, 320-326.
-
[1]
计量
- PDF下载量: 5
- 文章访问数: 2465
- HTML全文浏览量: 102