Synthesis and Biological Activity of Novel Phosphoramidate with Hydantoin

doi:10.6023/cjoc201210046

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (03): 596-601.DOI: 10.6023/cjoc201210046 Previous Articles Next Articles

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含咪唑啉2,4-二酮的新型磷酰胺酯类化合物的合成和生物活性

韩金涛^a, 王进敏^a, 董宏波^a, 徐志红^a,b, 刘斌^a, 王明安^a

a 中国农业大学应用化学系北京 100193;
b 长江大学农学院荆州 434205

收稿日期:2012-10-29 修回日期:2012-11-28 发布日期:2012-12-03
通讯作者: 王明安 E-mail:wangma@cau.edu.cn
基金资助:
“十二五”科技支撑计划(No. 2011BAE06B03)、国家自然科学基金(No. 20772150)和南开大学元素有机化学国家重点实验室开放基金(Nos. 0902, 201003)资助项目.

Synthesis and Biological Activity of Novel Phosphoramidate with Hydantoin

Han Jintao^a, Wang Jinmin^a, Dong Hongbo^a, Xu Zhihong^a,b, Liu Bin^a, Wang Mingan^a

a Department of Applied Chemistry, China Agricultural University, Beijing 100193;
b College of Agricuture, Yangtze University, Jingzhou 434025

Received:2012-10-29 Revised:2012-11-28 Published:2012-12-03
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 (Nos. 0902, 201003).

Based on the synthesis of phosphates and phosphorylamides with hydantoin, the natural inhibitor of AdSS and its activated hydantocidin-5'-phosphate in the plant, eighteen new O-alkyl-N-alkyl-5-[4-hydroxy-3-nitrophenyl(benzyl)]-2,4- imidazolidinedione thiophosphoramidate derivatives with hydantoin were synthesized by the reaction of O,N-dialkyl thiophosphoryl chloride with 5-(4-hydroxy-3-nitrophenyl)- and 5-(4-hydroxy-3-nitrobenzyl)-2,4-imidazolidinedione intermediates, and their structures were confirmed by IR, ¹H NMR, ³¹P NMR spectral data and elemental analysis. The preliminary bioassay showed that O-ethyl(propyl)-N-isopropyl-5-(4-hydroxy-3-nitrobenzyl)-2,4-imidazolidinedione thiophosphoramidates (B10 and B16) have inhibitory rates of 64.1% and 69.6% against Brasica campestris at the concentration of 100 μg/mL, while O-propyl-N-butyl-5-(4-hydroxy-3-nitrobenzyl)-2,4-imidazolidinedione thiophosphoramidate (B15) showed 100%, and 95% insecticidal activities against Myzus persicae and Plutella xylostella at the concentration of 300 μg/mL.

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

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Han Jintao, Wang Jinmin, Dong Hongbo, Xu Zhihong, Liu Bin, Wang Mingan. Synthesis and Biological Activity of Novel Phosphoramidate with Hydantoin[J]. Chin. J. Org. Chem., 2013, 33(03): 596-601.

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[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) Wrasidlo, W.; Elliott, G. I.; Carson, D. A.; Rosenbach, M. WO 2009023495, 2009 [Chem. Abstr. 2009, 150, 252697].
(e) Zhang, Y.; Elliott, G. I.; Saldanha, A.; Carson, D. A.; Wrasidlo, W. Beilstein J. Org. Chem. 2010, 6, 742.

[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] Wang J.-M. Ph.D Dissertation, China Agricultural University, Beijing, 2010 (in Chinese).
(王进敏, 博士论文, 中国农业大学, 北京, 2010.)

[12] Yang, H. Z.; Zou, X. M.; Wang, L. G.; Cheng, M. R. J. Central Chin. Normal Univ. 2006, 40, 532 (in Chinese).
(杨华铮, 邹小毛, 王磊光, 程慕如, 华中师范大学学报, 2006, 40, 532.)

[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] Huang, Z. X.; Ough, C. S. J. Agric. Food. Chem. 1991, 39, 2218.

[15] 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.)

[16] Wang, Z. D.; Sheikh, S. O.; Zhang, Y. Molecules 2006, 11, 739.

[17] Chalmers, J. R.; Dickson, G. T.; Elks, J.; Hems, B. A. J. Chem. Soc. 1949, 3424.

[18] 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.)

[19] Zhang, D. K.; Li, G. W. Chem. J. Chin. Univ. 1982, 3, 77 (in Chinese).
(张殿坤, 李国炜, 高等学校化学学报, 1982, 3, 77.)
[20] Chen, R. Y.; Yang, H. Z.; Xing, X. D.; Zhang, Z. P.; Wang, L. X.; Cheng, M. R.; Li, F. X.; Wang, H. L. Chem. J. Chin. Univ. 1985, 6, 897 (in Chinese).
(陈茹玉, 杨华铮, 邢晓东, 张政朴, 王玲秀, 程慕如, 李复信, 王惠林, 高等学校化学学报, 1985, 6, 897.)

含咪唑啉2,4-二酮的新型磷酰胺酯类化合物的合成和生物活性

Synthesis and Biological Activity of Novel Phosphoramidate with Hydantoin

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