Functions of phosphorus moiety in agrochemical molecules

Bioscience, Biotechnology and Biochemistry

Volumn 61, Issue 1, 1997, Pages 1-11

  Eto, Morifusa ^a,b  

^a MIYAKONOJO NATIONAL COLLEGE OF TECHNOLOGY   (Japan)

^b KYUSHU UNIVERSITY   (Japan)

Author keywords

Alkylation; Phosphorylation; Stereochemical aspect; Stressor; Transition state analog inhibition

Indexed keywords

EID: 0031000812     PISSN: 09168451     EISSN: 13476947     Source Type: Journal    
DOI: 10.1271/bbb.61.1     Document Type: Article

References (86)

1. S. Shibuya and I. Shimazaki, “Shibuya Index,” 7th Ed., Zen-Noh, Kumiai Chem. Ind., Tokyo, 1996.
2. F. H. Westheimer, Science, 235, 1173-1178 (1987).
3. V. M. Clark, D. W. Hutchinson, A. J. Kirby, and S. G. Warren, Angew. Chem. Int. Ed., 3, 678-685 (1964).
4. M. Eto, “Organophosphorus Pesticides: Organic and Biological Chemistry,” CRC Press, Cleveland, 1974.
5. M. Eto, S. Okabe, Y. Ozoe, and K. Maekawa, Pestic. Biochem. Physiol., 7, 367-377 (1977).
6. K. D. Wing, A. H. Glickman, and J. E. Casida, Pestic. Biochem. Physiol., 21, 22-30 (1984).
7. Y. Kono, Y. Sato, and Y. Okuda, Pestic. Biochem. Physiol., 20, 225-231 (1983).
8. D. B. Boyd, J. Am. Chem. Soc., 91, 1200-1205 (1969).
9. E. T. Kaiser, T. W. S. Lee, and F. P. Boer, J. Am. Chem. Soc., 93, 2351-2353 (1971).
10. F. Ramirez, J. F. Marecek, and H. Okazaki, J. Am. Chem. Soc., 97, 7181-7183 (1975).
11. M. Eto, S. Tawata, K. Sakamoto, and K. Oshima, J. Pestic. Sei., 3, 161-163 (1978).
12. M. Eto, J. Environ. Sei. Health, B18, 119-145 (1983).
13. S. Tashiro, E. Taniguchi, and M. Eto, Science, 175,448-449 (1972).
14. A. Hirashima and M. Eto, Agric. Biol. Chem.,47,2831-2839(1983).
15. S.-Y. Wu, R. Takeya, M. Eto, and C. Tomizawa, J. Pestic. Sei., 12, 221-227 (1987).
16. S.-Y. Wu, A. Hirashima, R. Takeya, and M. Eto, Agric. Biol. Chem., 53, 165-174(1989).
17. M. Eto, Rev. Plant Protec. Res., 9, 1-20 (1976).
18. M. Eto, J. E. Casida, and T. Eto, Biochem. Pharmacol., 11, 337-352 (1962).
19. M. Eto, Y. Kinoshita, T. Kato, and Y. Oshima, Nature, 200, 171-172 (1963).
20. M. Eto, N. Fukuhara, E. Kuwano, and H. Koyama, Agric. Biol. Chem., 45, 915-923 (1981).
21. J. A. Gerlt, N. I. Gutterson, P. Dalta, B. Belleau, and C. L. Penney, J. Am. Chem. Soc., 102, 1655-1660 (1980).
22. S.-Y. Wu, S. Ito, and M. Eto, Agric. Biol. Chem., 51, 2935-2942 (1987).
23. M.-Y. Eto, M. Ito, Y. Kobayashi, H. Omura, and M. Eto, Agric. Biol. Chem., 38, 2081-2092 (1974).
24. M. Sasaki, in “Bioorganic Chemistry of Pesticides,” ed. by M. Eto, Soft Science, Tokyo, 1985, pp. 210-222.
25. M. Eto, in “Chemistry of Plant Protection,” Vol. 6, Springer-Verlag, Berlin, 1990, pp. 65-107.
26. L. P. A. De Jong and H. P. Benshop, in “Stereoselectivity of Pesticides Biological and Chemical Problems,” ed. by E. J. Afiens, J. J. S. Van Resen, and W. Welling, Elsevier, Amsterdam, 1988, pp. 109-149.
27. D. A. Wustner and T. R. Fukuto, Pestic. Biochem. Physiol., 4, 365-376 (1974).
28. D. A. Wustner and T. R. Fukuto, J. Agric. Food Chem., 21, 756-761 (1973).
29. A. Miyazaki, T. Nakamura, M. Kawaradani, and S. Marumo, J. Agric. Food Chem., 36, 835-837 (1988).
30. J. Järv, A. Aaviksaar, N. Godovikov, and D. Lobanov, Biochem. J., 167, 823-825 (1977).
31. H. A. Berman and K. Leonard,/Biol. Chem., 264,3942-3950(1989).
32. J. L. Sussman, M. Harel, F. Frolow, C. Oefner, A. Goldman, L. Toker, and I. Silman, Science, 253, 872-879 (1991).
33. A. Hirashima, I. Ishaaya, R. Ueno, Y. Ichiyama, S.-Y. Wu, and M. Eto, Agric. Biol. Chem, 53, 175-178 (1989).
34. A. Hirashima, R. Ueno, K. Oyama, H. Koga, and M. Eto, Agric. Biol. Chem., 54, 1013-1022 (1990).
35. A. Hirashima, T. Nagano, R. Oishi, and M. Eto, Comp. Biochem. Physiol., 104C, 395-399 (1993).
36. E. L. Becker, T. R. Fukuto, D. C. Canham, and E. Boger, Biochem., 2, 72-76 (1963).
37. J. R. Grothusen and T. M. Brown, Pestic. Biochem. Physiol., 26, 100-106 (1986).
38. J. E. Casida, R. L. Baron, M. Eto, and J. L. Engel, Biochem. Pharmacol., 12, 73-83 (1963).
39. H. Ohkawa, H. Oshita, and J. Miyamoto, Biochem. Pharmacol., 29, 2721-2727 (1980).
40. M. K. Johnson, Rev. Biochem. Toxicol., 4, 141-212 (1982).
41. H. Ohkawa, H. Oshita, and J. Miyamoto, Agric. Biol. Chem., 42, 1745-1751 (1978).
42. M. Yoshida, S.-Y. Wu, and J. E. Casida, Toxicol. Letters, 74,167-176 (1994).
43. S. -Y. Wu, in “Progress and Prospects of Organophosphorus Agrochemicals,” ed. by M. Eto and J. E. Casida, 1995, Kyushu Univ. Press, pp. 89-111.
44. H. Ohkawa and M. Eto, Agric. Biol. Chem., 33, 443-451 (1969).
45. T. Shiotsuki, A. Koiso, andM. Eto, J Pestic. Sei., 14,337-344(1989).
46. T. Shiotsuki, T. Kakimoto, and M. Eto, Pestic. Biochem. Physiol., 42, 119—127 (1992).
47. A. Manabe and M. Eto, J Pestic. Sei., 8, 363-366 (1983).
48. S. Kurogochi, M. Katagiri, I. Takase, and Y. Uesugi, JPestic. Sei., 10, 41-46 (1985).
49. M. Eto, Y. Hashimoto, K. Ozaki, T. Kassai, and Y. Sasaki, Botyu-Kagaku, 40, 110—117 (1975).
50. H. A. Berman and M. M. Decker, J Biol. Chem., 264, 3951-3956 (1989).
51. C. M. Thompson, C. E. Berkman, and A. I. Suary, in “Progress and Prospects of Organophosphorus Agrochemicals,” ed. by M. Eto and J. E. Casida, Kyushu Univ. Press, 1995, pp. 71-87.
52. M. K. Johnson, I. Bird, and C. Meredith, Toxicol. Lett., 40, 133-140 (1988).
53. Y. Ozoe, K. Mochida, and M. Eto, Agric. Biol. Chem., 46, 555-556 (1982).
54. J. E. Casida, M. Eto, A. D. Moscioni, J. L. Engel, D. S. Milbrath, and J. Verkade, Toxicol. Appl. Pharmacol., 36, 261-279 (1976).
55. M. Eto, Y. Ozoe, T. Fujita, and J. E. Casida, Agric. Biol. Chem., 40, 2113-2115 (1976).
56. N. G. Bowery, J. F. Collins, and R. G. Hill, Nature, 261, 601-603 (1976).
57. S. Korenaga, Y. Ito, Y. Ozoe, and M. Eto, Comp. Biochem. Physiol., 57C, 95-100 (1977).
58. R. F. Squires, J. E. Casida, M. Richardson, and E. Saederup, Mol. Pharmacol., 23,326-336 (1983).
59. Y. Ozoe and M. Eto, in “Membrane Receptors and Enzymes as Targets of Insecticidal Action,” ed. by J. M. Clark and F. Matsumura, Plenum, New York, 1986, pp. 75-105.
60. C. J. Palmer and J. E. Casida, in “A Site of Action for Neurotoxic Pesticides,” ed. by R. M. Hollingworth and M. B. Green, ACS Symposium Ser., 356, 1987, pp. 71-82.
61. C. J. Palmer, I. H. Smith, M. D. V. Moss, and J. E. Casida, J. Agric. Food Chem., 38, 1091-1093 (1990).
62. Y. Deng, C. J. Palmer, and J. E. Casida, Pestic. Biochem. Physiol., 41, 60-65 (1991).
63. Y. Deng, C. J. Palmer, and J. E. Casida, Pestic. Biochem. Physiol., 47, 98-112 (1993).
64. M. Sasaki, T. Kato, S. Yamamoto, and K. Mukai, J. Pestic. Sei., 9, 717-723 (1984).
65. M. Sasaki, H. Takano, and T. Kato, Agric. Biol. Chem., 51, 1727-1728 (1987).
66. J. Jung, in “Bioregulators for Pest Control,” ACS Symposium Ser., 276, 1985, pp. 95-107.
67. R. J. Linderman, T. Tshering, K. Venkatesh, D. R. Goodlett, W. C. Dauterman, and R. M. Roe, Pestic. Biochem. Physiol., 39, 57-73 (1991).
68. M. S. Malik, R. S. Vetter, T. C. Baker, and T. R. Fukuto, Pestic. Sei., 32, 35-46 (1991).
69. P. Wieczorek, B. Lejczak, M. Kaczanowska, and P. Kafarski, Pestic. Sei., 30, 43-57 (1990).
70. L. M. Abell, W. S. Hanna, K. J. Kunitsky, and J. A. Kerscher, Pestic. Sei., 44, 89-92 (1995).
71. A. C. Baillie, K. Wright, B. J. Wright, and C. G. Eamshaw, Pestic. Biochem. Physiol., 30, 103-112 (1988).
72. A. I. Biryukov, I. G. Vasilyeva, Y. N. Zhukov, E. N. Khurs, and R. M. Khomutov, Pestic. Sei., 30, 321-323 (1990).
73. J. G. Allen, F. R. Atherton, J. J. Hall, C. H. Hassall, S. W. Holmes, R. W. Lambert, L. J. Nisbet, and P. S. Ringrose, Nature, 272, 56-58 (1978).
74. L. Cerenius, S. Rufelt, and K. Soderhall, Pestic. Sei., 36, 189-194 (1992).
75. E. W. Logusch, D. W. Walker, J. F. McDonald, and J. E. Franz, Biochem., 28, 3043-3051 (1989).
76. J. A. Sikorski and E. W. Logusch, in “Handbook of Organophosphorus Chemicals,” ed. by R. Engel, Marcel Dekker, New York, 1992, pp. 739-805.
77. R. F. Platt, Science, 246, 917-919 (1989).
78. H. C. Steinrucken and N. Amrhein, Eur. J. Biochem., 143, 351-357 (1984).
79. S. Castellino, G. C. Leo, R. D. Sammons, and J. A. Sikorski, Biochemistry, 28, 3856-3868 (1989).
80. F. M. Kahan, J. S. Kahan, P. J. Cassidy, and H. Kropp, Ann. N. Y. Acad. Sei., 235, 364-386 (1974).
81. E. Helgstrand, B. Eliksson, N. G. Johnansson, B. Lannero, A. Larsson, A. Misiorny, J. O. Noren, B. Sjoberg, K. Stenberg, G. Sterring, S. Stridh, B. Oberg, S. Alenius, and C. Philipson, Science, 201, 819-821 (1978).
82. T. Bachietto, P. Saidrenau, and G. Bompeix, Pestic. Biochem. Physiol., 42, 151-166 (1992).
83. K. R. Jennings, A. N. Starratt, and R. W. Steele, Pestic. Biochem. Physiol., 19, 122-132 (1983).
84. A. Hirashima, K. Oyama, and M. Eto, Pesitc. Biochem. Physiol., 38, 186-195 (1990).
85. A. Hirashima, T. Nagano, and M. Eto, Biosci. Biotech. Biochem., 57, 2085-2089 (1993).
86. A. Hirashima, T. Nagano, R. Takeya, and M. Eto, Comp. Biochem. Physiol., 106C, 457-461 (1993).