Citation: ZHOU Yuan, YOU Ge-Yun, PENG Hao, HE Hong-Wu. 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[J]. Chinese Journal of Structural Chemistry, ;2016, 35(6): 857-862. doi: 10.14102/j.cnki.0254-5861.2011-1051 shu

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

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Key Laboratory of Pesticide and Chemical Biology, Ministry of Education and College of Chemistry, Central China Normal University, Wuhan 430079, China

Corresponding author: PENG Hao,
Received Date: 12 November 2015
Available Online: 1 April 2016
Fund Project: and excellent doctorial dissertation cultivation grant from Central China Normal University (No. 2015YBYB116) (No. 2014CFA111)

A new crystal of (E)-2-(2,4-dichlorophenoxy)-1-(5,5-dimethyl-2-oxido-1,3,2-dioxa- phosphinan-2-yl)vinyl 2-(2,4-dichlorophenoxy)acetate has been determined by single-crystal X-ray diffraction. The compound crystallizes in triclinic, space group P with a = 7.9393(17), b = 11.974(3) Å, c = 13.532(3) Å, α = 90.937(4), β = 101.998(3), γ = 101.363(4)°, V = 1231.5(5) Å³, D_c = 1.500 Mg/m³, Z = 2, F(000) = 568 and μ = 0.585 mm^-1. The molecular packing in the crystal is the result of C(10)–H(10)…O(5) hydrogen bond, as well as weak π-π stacking interactions. The herbicidal activity results indicated that the title compound 3 showed 80~100% inhibitory activities against all of the tested weeds at a dosage of 150 g·ai/ha.
- X-ray crystallography,
- phosphonate,
- (E)-vinyl acetate,
- herbicidal activity
1. [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.
2. [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.
3. [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.
4. [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.
5. [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.
6. [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.
7. [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.
8. [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.
9. [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.
10. [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.
11. [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.
12. [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.
13. [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.
14. [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.
15. [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.
16. [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.
17. [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.
18. [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.
19. [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.
20. [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.
21. [21]
  (21) Robin, T.; Olga, K. Hydrogen-bond geometry in organic crystals. Acc. Chem. Res. 1984, 17, 320-326.
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