Synthesis and pesticidal properties of thio and seleno analogs of some common urea herbicides

Phosphorus, Sulfur and Silicon and the Related Elements

Volumn 184, Issue 7, 2009, Pages 1880-1903

  Zakrzewski, Jerzy ^a   Krawczyk, Maria ^a  

^a INSTITUTE OF INDUSTRIAL ORGANIC CHEMISTRY   (Poland)

Author keywords

Isocyanides; Isoselenocyanates; Isothiocyanates; Selenoureas; Thioureas; Urea herbicides

Indexed keywords

EID: 70449631476     PISSN: 10426507     EISSN: 15635325     Source Type: Journal    
DOI: 10.1080/10426500802391692     Document Type: Article

References (70)

1. P. K. Mohanta, S. Dhar, S. K. Samal, H. Ila, and H. Junjappa, Tetrahedron, 56, 629 (2000), and references cited therein.
2. A. Kaluszyner, R. Mechoulam, and M. Breuer, Bull. Res. Council Israel, 7A, 135 (1958).
3. D. Duerr and M. von Orelli, Ciba, Patent US 3927087 (1975).
4. R. Spaun, P. Brenneisen, A. Rochat, and J. Gallay, Agripat S. A.; Patent CH 542828 (1973);
5. Patent DE 2143838, US3781290 (1972);
6. Chem. Abstr., 77, 48078 (1972).
7. H. Martin, D. Duerr; A. Hubele, J. Rufener, G. Pissiotas, and O. Rohr, Ciba-Geigy AG, Patent DE 2157288, US 3799759 (1972);
8. Chem.Abstr., 77, 97750 (1972).
9. D. Duerr and V. Dittrich, Ciba; Patent US 3395233, NL 6604132 (1966);
10. Chem. Abstr., 66, 55249 (1967).
11. E. Rodŕ̈guez-Ferńandez, J. L. Manzano, J. J. Benito, R. Hermosa, E. Monte, and J. J. Criado, J. Inorg. Biochem., 99, 1558 (2005).
12. H. Takahashi, A. Nishina, R. Fukumoto, H. Kimura, M. Koketsu, and H. Ishihara, Life Sci., 76, 2185 (2005).
13. H. Tsukagoshi, M. Koketsu, M. Kato, M. Kurabayashi, A. Nishina, and H. Kimura, FEBS J., 274, 6046 (2007).
14. S. K. Ha, M. Koketsu, K. Lee, S. Y. Choi, J. H. Park, H. Ishihara, and S. Y. Kim, Biol. Pharm. Bull., 28, 838 (2005).
15. P. N. Jayram, G. Roy, and G. Mugesh, J. Chem. Sci., 120, 143 (2008).
16. S. Braverman, M. Cherkinsky, and M. L. Birsa, In: Science of Synthesis (Thieme, Stuttgart, 2005), Vol.18, pp. 65-320 .
17. H. Heimgartner, Y. Zhou, P. K. Atanassow, and G. L. Sommen, Phosphorus, Sulfur, and Silicon, 183, 840 (2008).
18. D. R. Garud, M. Koketsu, and H. Ishihara, Molecules,̈12, 504 (2007).
19. J. Zakrzewski, J. Jezierska, and J. Hupko, Org. Lett., 6, 695 (2004).
20. J. Zakrzewski and M. Krawczyk, Heteroatom Chem., 19, 549 (2008).
21. C. R. Worthing, Ed., The Pesticide Manual, 8th ed., The British Crop Protection Council, 1987;
22. C. D. S. Tomlin, Ed., The e-Pesticide Manual, 13th ed., The British Crop Protection Council, 2003.
23. G. C. Klingman, F. M. Ashton, and L. J. Noordhoff, Weed Sciences: Principles and Practices (Wiley, New York, 1975), pp. 238-248.
24. B. E. Watt, A. T. Proudfoot, S. M. Bradberry, and J. A. Vale, Toxicol. Rev., 24, 161 (2005).
25. R. F. Hunter and E. R. Styles, J. Chem. Soc., 1209 (1927).
26. G. V. Nair, J. Indian Chem. Soc., 42, 359 (1965).
27. K. Ramadas and N. Janarthanan, Synth. Commun., 27, 2357 (1997).
28. D. L. Klayman and R. J. Shine, J. Org. Chem., 34, 3549 (1969).
29. D. L. Klayman, C. Chase, and R. J. Shine, Secret. Army; Patent US 3597444 (1971);
30. Chem. Abstr., 75, 88352 (1971).
31. A. M. Kirkien and R. J. Shine, Org. Mass Spectrom., 7, 233 (1973).
32. S. Braverman, M. Cherkinsky, and M. L. Birsa, In Science of Synthesis (Thieme, Stuttgart, 2005), Vol.18, pp. 65-320 (especially pp. 189-191) .
33. J. Zakrzewski, J. Hupko, and K. Kryczka, Monatsh. Chem., 134, 843 (2003).
34. I. Ugi, Ed., Isonitrile Chemistry (Academic Press, New York, 1971).
35. M. P. Periasamy and H. M. Walborsky, Org. Prep. Proc. Int., 11, 293 (1979).
36. H. M. Walborsky and M. P. Periasamy, In S. Patai and Z. Rappaport, Eds., The Chemistry of Triple Bonded Functional Groups (Wiley, New York, 1983), pp. 835- 887.
37. M. Suginome and Y. Ito, In Science of Synthesis (Thieme, Stuttgart, 2004), Vol.19, pp. 445-530 (especially pp. 478-480).
38. W. P. Weber and G. W. Gokel, Angew. Chem., Int. Ed., 11, 530 (1972).
39. W. P. Weber and G. W. Gokel, Tetrahedron Lett., 1637 (1972).
40. L. M. Rajchman, B. Annaev, V. S. Belova, and E. G. Rozantsev, Nature (London), 237, 31 (1972).
41. S. Braverman, M. Cherkinsky, and M. L. Birsa, In, Science of Synthesis (Thieme, Stuttgart, 2005), Vol.18, pp. 65-320 (especially pp. 252-254).
42. P. Kristian and G. Suchar, Coll. Czech. Chem. Commun., 37, 3066 (1972).
43. J. Zakrzewski and M. Krawczyk, Heteroatom Chem., 17, 393 (2006).
44. G. I. Kokorev, F. D. Yambushev, and L. A. Al'metkina, Zh. Obshch. Khim., 58, 829 (1988);
45. J. Gen. Chem. USSR, 58, 733 (1988).
46. R. Wong and S. J. Dolman, J. Org. Chem., 72, 3969 (2007).
47. R. N. Butler and L. M. Wallace, J. Chem. Soc., Perkin Trans. 1, 4335 (2000).
48. D. W. Browne and G. M. Dyson, J. Chem. Soc., 3285 (1931).
49. M. M. Kamel, Pharmazie, 37, 147 (1982).
50. X. Zhang, Y. K. Lee, J. A. Kelley, and T. R. Burke, J. Org. Chem., 65, 6237 (2000).
51. Aldrich Handbook of Fine Chemicals, Sigma-Aldrich Co., 2007-2008.
52. R. G. Jones and G. Allen, Org. Magn. Reson., 19, 196 (1982).
53. Japan Soda Co., Patent JP 569563, 1963;
54. Chem. Abstr., 60, 7387 (1964).
55. B. R. de Costa, K. C. Rice, W. D. Bowen, A. Thurkauf, R. B. Rothman, L. Band, A. E. Jacobson, L. Radesca, P. C. Contreras, N. M. Gray, I. Daly, S. Iyengar, D. T. Finn, S. Vazirani, and J. M. Walker; J. Med. Chem., 33, 3100 (1990).
56. M. Dai, C. Wang, G. Dong, J. Xiang, T. Luo, B. Liang, J. Chen, and Z. Yang, Eur. J. Org. Chem., 4346 (2003).
57. K. Yonemoto and I. Shibuya, Bull. Chem. Soc. Jpn., 61, 4043 (1988).
58. A. P. Krapcho, J. Org. Chem., 27, 1089 (1962).
59. T. Mukaiyama, K. Tonooka, and K. Inoue, J. Org. Chem., 26, 2202 (1961).
60. A. Guirado, A. Zapata, J. L. Gomez, L. Trabalon, and J. Galvez, Tetrahedron, 55, 9631 (1999).
61. I. Ugi, U. Fetzer, G. Unterstenhoefer, W. Behrenz, P.-E. Frohberger, and H. Scheinpflug, Bayer, Patent FR 1384209, 1965;
62. Chem. Abstr., 63, 6924 (1965).
63. D. H. R. Barton, S. I. Parekh, M. Tajbakhsh, E. A. Theodorakis, and C. L. Tse, Tetrahedron, 50, 639 (1994).
64. L. Henriksen and U. Ehrbar, Synthesis, 519 (1976).
65. A. M. Boccanfuso, D. W. Griffin, R. B. Dunlap, and J. D. Odom, Bioorg. Chem., 17, 231 (1989).
66. Z. J. Witczak, Tetrahedron, 41, 4781 (1985).
67. J. J. Ares, J. W.Fowble, T. G. Urchek, and D. D. Miler, Biochem. Biophys. Res. Commun., 142, 1064 (1987).
68. A. V. Peretokin, A. D. Shutalev, V. V. Chupin, A. M. Mergenova, L. A. Ignatova, Yu. F. Malina, and B. V. Unkovskii, Zh. Org. Chem., 21, 1004 (1985);
69. Chem. Abstr., 104, 108981 (1986).
70. J. Imrich, T. Busova, P. Kristian, and J. Dzara, Chem. Pap., 48, 42 (1994)..