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Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 10: 2186 - 2195

DOI: https://doi.org/10.6023/cjoc201305023

Articles

Synthesis and Biological Activity of Novel Phosphoramide with Hydantoin

  • Wang Jinmin ,
  • Xu Zhihong ,
  • Han Jintao ,
  • Dong Hongbo ,
  • Liu Bin ,
  • Wang Mingan
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  • a Department of Applied Chemistry, China Agricultural University, Beijing 100193;
    b College of Agricuture, Yangtze University, Jingzhou 434025

Received date: 2013-05-14

  Revised date: 2013-06-11

  Online published: 2013-06-21

Supported by

Project supported by the National Key Technologies R&D Program (No. 2011BAE06B03), the National Natural Science Foundation of China (No. 20772150) and the National Key Laboratory of Elemento-Organic Chemistry in Nankai University (No. 0902, 201003).

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Abstract

Based on the synthesis of phosphates and phosphorylamidates with hydantoin, thirty and eight new O,O-dialkyl-(aryl)-5-[4-aminophenyl(benzyl)]-2,4-imidazolidinedione thiophosphoramide derivatives with hydantoin were synthesized by the reaction of O,O-dialkyl(aryl) thiophosphoryl chloride with 5-(4-aminophenyl)-and 5-(4-aminobenzyl)-2,4-imidazolidine-dione intermediates, and their structures were confirmed by 1H NMR, 31P NMR, IR, elemental analysis and X-ray diffraction. 9b: C14H20N3O3PS2·1/3H2O, Mr=379.43, triclinic, space group P-1, a=0.82092(5) nm, b=1.79810(14) nm, c=2.0153(2) nm, α=72.289(8)°, β=79.355(7)°, γ=77.288(6)°, V=2.7421(4) nm3, Dc=1.379 g/cm3, Z=6, F(000)=1196, μ(Mo Kα)=0.397 mm-1, S=1.031, final R=0.0426, wR=0.0797. The preliminary bioassay showed that O,O-dimethyl-5-(4-amino-phenyl)-2,4-imidazolidinedione thiophosphoramide (7a), O-ethyl-O-phenyl-5-(4-aminobenzyl)-2,4-imidazolidine-dione thio-phosphoramide (9n) and O,O-dimethyl-5-(3-aminophenyl)-2-thio-2,4-imidazolidinedione thiophosphoramide (11a)have inhibitory rates 75.4%, 80.5% and 81.7% against Brasica campestris at the concentration of 100 μg/mL, while eleven compounds showed excellent insecticidal activities against Myzus Persicae with the LD50 data in the range of 182.41～368.52 μg/mL, respectively.

Key words： 2,4-imidazolidinedione; thiophosphoramide; adenylosuccinate synthetase; biological activity

Cite this article

Wang Jinmin , Xu Zhihong , Han Jintao , Dong Hongbo , Liu Bin , Wang Mingan . Synthesis and Biological Activity of Novel Phosphoramide with Hydantoin[J]. Chinese Journal of Organic Chemistry, 2013 , 33(10) : 2186 -2195 . DOI: 10.6023/cjoc201305023

References

[1] Fonné-Pfister, R.; Chemla, P.; Ward, E.; Girardet, M.; Kreuz, K. E.; Honzatko, R. B.; Fromm, H. J.; Schar, H. P.; Grutrers, M. G.; Cowan-Jacob, S. W. Proc. Natl. Acad. Sci. U. S. A. 1996, 93, 9431.
[2] Nakajima, N.; Itoi, K.; Takamatsu, Y.; Kinoshita, T.; Okazaki, T.; Kawakubo, K.; Shindo, M.; Honma, T.; Tohjigamori, M.; Haneishi, T. J. Antibiot. 1991, 44, 293.
[3] Heim, D. R.; Cseke, C.; Gerwick, B. C.; Murdoch, M. G.; Green, S. B. Pestic. Biochem. Physiol. 1995, 53, 138.
[4] Siehl, D. L.; Subramanian, M. V.; Walters, E. W.; Lee, S. F.; Anderson, F. J.; Toschi, A. G. Plant Physiol. 1996, 110, 753.
[5] (a) Walters, E. W.; Lee, S.-F.; Niderman, T.; Bernasconi, P.; Subramanian, M. V.; Siehl, D. L. Plant Physiol. 1997, 114, 549.
(b) Cseke, C. T.; Gerwick, B. C.; Crouse, B. C.; Murdoch, M. G.; Green, S. B.; Heim, D. R. Pestic. Biochem. Physiol. 1996, 55, 210.
[6] (a) Poland, B. W.; Silva, M. M.; Serra, M. A.; Cho, Y.; Kim, K. H.; Harris, E. M.; Honzatko, R. B. J. Biol. Chem. 1993, 268, 25334.
(b) Poland, B. W.; Hou, Z. L.; Bruns, C.; Fromm, H. J.; Honzatko, R. B. J. Biol. Chem. 1996, 271, 15407.
[7] (a) Wang, J. M.; Han, J. T.; Kuang, Y.; Jin, S. H.; Wang, M. A. Chin. J. Pestic. Sci. 2008, 10, 392 (in Chinese). (王进敏, 韩金涛, 匡宇, 金淑惠, 王明安, 农药学学报, 2008, 10, 392.)
(b) Wang, J. M.; Kuang, Y.; Han, J. T.; Jin, S. H.; Wang, M. A. Chin. J. Pestic. Sci. 2009, 11, 1 (in Chinese).(王进敏, 匡宇, 韩金涛, 金淑惠, 王明安, 农药学学报, 2009, 11, 1.)
[8] (a) Crouse. G. D.; Johnston, R. D.; Heim, D. R.; Cseke, C. T.; Webster, J. D. Synthesis and Chemistry of Agro-chemicals V, Washington DC, American Chemical Society, 1998, Chapter 13, pp. 120～133.
(b) Hanessian, S.; Lu, P. P.; Sancéau, J. Y.; Chemla, P.; Gohda, K.; Fonne-Pfister, R.; Prade, L.; Cowan-Jacob, S. W. Angew. Chem., Int. Ed. 1999, 38, 3160.
(c) Tibrewal, N.; Elliott, G. I. Bioorg. Med. Chem. Lett., 2011, 21, 517.
(d) Zhang, Y.; Elliott, G. I.; Saldanha, A.; Carson, D. A.; Wrasidlo,
W. Beilstein J. Org. Chem. 2010, 6, 742.
(e) Boitz, J. M.; Strasser, R.; Yates, P. A.; Jardim, A.; Ullman, B. J. Biol. Chem. 2013, 288, 8977.
(f) Wiest, A.; McCarthy, A. J.; Schnittker, R.; McCluskey, K. J. Genet. 2012, 91, 199.
[9] Wang, Y. P.; Wang, M. A.; Du, F. P.; Li, X. D.; Yao, G. W.; Zhang, P. D.; Lu, H. Z. Chem. J. Chin. Univ. 2010, 31, 336 (in Chinese).(汪月鹏, 王明安, 杜凤沛, 李向东, 姚广伟, 张潘丹, 路慧哲, 高等学校化学学报, 2010, 31, 336.)
[10] Xu, Z. H.; Wang, J. M.; Han, J. T.; Liu, B.; Wang, M. A. Chin. J. Org. Chem. 2012, 32, 2134 (in Chinese). (徐志红, 王进敏, 韩金涛, 刘斌, 王明安, 有机化学, 2012, 32, 2134.)
[11] Han, J. T.; Wang, J. M.; Dong H. B.; Xu, Z. H.; Liu, B.; Wang, M. A. Chin. J. Org. Chem. 2013, 33, 596 (in Chinese).(韩金涛, 王进敏, 董宏波, 徐志红, 刘斌, 王明安, 有机化学, 2013, 33, 596.)
[12] Connors, T. A.; Ross, W. C. J.; Wilson, J. G. J. Chem. Soc. 1960, 2994.
[13] Wang, J. M.; Han, J. T.; Zhang, C. Y.; Qiu, L. H.; Wang, M. A. Chin. J. Org. Chem. 2010, 30, 72 (in Chinese).(王进敏, 韩金涛, 张春艳, 邱立红, 王明安, 有机化学, 2010, 30, 72.)
[14] Burckhalter, J. H.; Stephens, V. C. J. Am. Chem. Soc., 1951, 73, 56.
[15] Wang, Z. D.; Sheikh, S. O.; Zhang, Y. Molecules 2006, 11, 739.
[16] Szeszel-Fedorowicz, W.; Lisowski, M.; Rosiñski, G.; Issberner, J.; Osborne, R.; Nopiñska, D. Polish J. Chem. 2001, 75, 411.
[17] Sassatelli, M.; Debiton, é.; Aboab, B.; Prudhomme, M.; Moreau P. Eur. J. Med. Chem. 2006, 41, 709.
[18] Han, J. T.; Wang, J. M.; Chen, S. C.; Qiu, L. H.; Wang, M. A. Chin. J. Org. Chem. 2010, 30, 691 (in Chinese).(韩金涛, 王进敏, 陈守聪, 邱立红, 王明安, 有机化学, 2010, 30, 691.)
[19] Huang, R. Q.; Wang, H. L.; Zhou, J. Preparation of Organic Intermediates, Chemical Industry Press, Beijing, 1997, p. 166 (in Chinese).(黄润秋, 王惠林, 周嘉, 有机中间体制备, 化学工业出版社, 北京, 1997, p. 166.)
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