Środki ochrony roślin o budowie chiralnej

• Autorzy: Morzycka B. , Morzycki J. W.

Warianty tytułu

EN

Chiral agrochemicals

• Języki publikacji: PL

Abstrakty

EN

The agrochemical industry is continuously searching for new active compounds to combat pests. The main aim of this research is to develop new substances with lower application rates, increased selectivity and decreased undesired ecological impact. Most synthetic agrochemicals with chiral structure are marketed as racemates even though the desired biological activity may be derived from only one enantiopure isomer. However, some newly introduced compounds are marketed as the most biologically active stereoisomers. When agrochemicals have chiral structures, efforts should be made to define the mode of action, toxicity, and metabolic pathway of each enantiopure isomer. If there are large differences in the biological activities of individual stereoisomers, it is desirable to use only the most active one. In this review article some stereochemical aspects of several groups of important agrochemicals including aryloxypropanoate herbicides, acylanilides, triazine herbicides, ureas and cyanoacrylates, triazole fungicides, morpholine derivatives, organochlorine insecticides, pyrethroid insecticides, pheromones and antifeedants, and organophosphorus compounds, will be discussed.

Słowa kluczowe

PL

stereochemia; związki chiralne; środki ochrony roślin

EN

stereochemistry; chiral compounds; agrochemistry

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Wiadomości Chemiczne
• Rocznik: 2003
• Tom: [Z] 57, 9-10
• Strony: 855--876
• Opis fizyczny: Bibliogr. 58 poz., schem.

Twórcy

autor

Morzycka B.

• Instytut Ochrony Roślin w Poznaniu, Stacja Doświadczalna w Białymstoku, ul. Chełmońskiego 22, 15-195 Białystok

autor

Morzycki J. W.

• Instytut Chemii, Uniwersytet w Białymstoku, al. J. Piłsudskiego 11/4, 15-443 Białystok

Bibliografia

• [1] G.M.R. Tombo, D. Belluś, Angew. Chem. Int. Ed. Engl., 1991, 30, 1193.
• [2] N. Kurihara, J. Miyamoto, G.D. Paulson, В. Zceh, M.W. Skidmore, R.M. Hollingworth, H.A. Kuiper, Pure&Appl. Chem., 1997, 69, 2007.
• [3] J. Crosby, Pestic. Sci., 1996, 46, 11.
• [4] L. Różański, Przemiany Pestycydów w Organizmach Żywych i Środowisku, PWRiL, Warszawa 1992.
• [5] D.A. Stuart, C.M. McCall, Plant Physiol., 1992, 99, 111.
• [6] S. Strathmann, M. Landes, В. Jung, Brighton Crop Prot. Conf., Weeds, 1991, tom 1, 429.
• [7] С. Dingier, W. Ladner, G.A. Krei, B. Cooper, B. Hauer, Pestic. Sci., 1996, 46, 33.
• [8] H. Dicks, J.W. Slater, D.W. Bewick, Weeds, 1985, 271.
• [9] J.D. Neber, J.S. van Rensen, [w:] Stereoselectivity of Pesticides, eds E.J. Ariens, J.J.S. van Rensen, W. Welling), Elsevier Science Publ., Amsterdam 1988, str. 263-287.
• [10] T. Poiger, M.D. Müller, H.-R. Buser, Chimia, 2002, 56, 300.
• [11] H.U. Blaser, H.P. Buser, K. Coers, R. Hanreich, H.P. Jalett, E. Jelsch, B. Pugin, H.D. Schneider, F. Spindler, A. Wegmann, Chimia, 1999, S3, 275.
• [12] H. Moser, G. Rihs, H. Sauter, Z. Naturforsch., 1982, B37, 452.
• [13] C.J. Sih, Q.M. Gu, X. Holdgrun, K. Harris, Chirality, 1992, 4, 91.
• [14] S. Fukui, T. Kawamoto, K. Sonomoto, A. Tanaka, Appl. Microbiol. Biotcchnol., 1990, 34, 330.
• [15] W. Sobótka, Pestycydy, 3-4, 1997, 5.
• [16] J-N. Phillips, [w:] Stereoselectivity of Pesticides, eds. E.J. Ariens, J.J.S. van Rensen, W. Welling, Elsevier Science Publ., Amsterdam 1988, str. 163-202.
• [17] W. Krämer, K.H. Buechel, W. Draber, [w:] IUPAC Pesticide Chemistry, Human Welfare and the Environment, eds J. Miyamoto, P.C. Kearney, Pergamon Press, New York 1983, tom 1, str. 223.
• [18] P. Gadher, E.I. Mercer, B.C. Baldwin, T.E. Wigging, Pestic. Biochem. Physiol., 1983, 19, 1.
• [19] Y. Funaki, Y. Ishiguri, T. Kato, S. Tanaka, [w:] IUPAC Pesticide Chemistry, Human Welfare and the Environment, eds J. Miyamoto, P.C. Kearney, Pergamon Press, New York 1983, tom 1, str. 309.
• [20] C. Vogel, T. Staub, G. Rist, E. Sturm, [w:] IUPAC Pesticide Chemistry, Human Welfare and the Environment, eds J. Miyamoto, P.C. Kearney, Pergamon Press, New York 1983, tom 1, str. 303.
• [21] E. Ebert, W. Eckhardt, K. Jäkel, P. Moser, D. Sozzi, C. Vogel, Z. Naturforsch. С, 1989, 44, 85.
• [22] W. Himmele, E.-H. Pommer, Angew. Chem. Int. Ed. Engl., 1980, 19, 184.
• [23] The British Crop Protection Council, The e-Pesticide Manual 2000 (wyd. XII), hasła : lindane i endosulfan.
• [24] M. Elliott, N.F. Janes, C. Potter, Ann. Rev. Entomol., 1978, 23, 443.
• [25] M. Elliott, A.W. Farnharn, N.F. Janes, P.H. Needham, D.A. Pulman, Insecticidally Active Conformations of Pyrethroids, [w:] Mechanism of Pesticide Action, eds G.K. Kohn, Waszyngton 1974, ACS Symp. Series, no. 2.
• [26] J.E. Chambers, Residue Review, 1980, 73, 101.
• [27] J.M. Barnes, R.D. Verschoyle, Nature, 1974, 248, 711.
• [28] H. Yoshioka, Rev. Plant Protection Res., 1978, 11, 39.
• [29] Y. Okuno, T. Seki, S, Ito, H. Kaneko, T. Watanabe, T. Yamada, J. Miyamoto, Toxicol. Appl. Pharmacol., 1986, 83, 157.
• [30] H. Sonawane, N.S. Bellur, J.R. Ahuja, D.G. Kulkami, Tetrahedron: Asymmetry, 1992, 3, 163.
• [31] M. Matsui, H. Yoshioka, H. Sakamoto, Y. Yamada, T. Kitahara, Agrie. Biol. Chem., 1967, 31, 33.
• [32] C.A. Henrick, B.A. Garcia, G.B. Staal, D.C. Cerf, R.J. Anderson, K. Gill, H.R. Chinn, J.N. Labovitz, M.M. Leippe, S.L. Woo, R.L. Carney, D.C. Gordon, G.K. Kohn, Pestic. Sci.,1980, 11, 224.
• [33] С. Beaulieu, С. Spino, Tetrahedron Lett., 1999, 40, 1637.
• [34] T. Aratani, Y. Yoneyoshi, T. Nagase, Tetrahedron Lett., 1982, 23, 685.
• [35] K. Mori, Tetrahedron, 1989, 45, 3233.
• [36] K. Oertle, H. Beyeler, R.O. Duthaler, W. Lottenbach, M. Riediker, E. Steiner, Helv. Chim. Acta, 1990, 73, 353.
• [37] J. Hurter, E.F. Boiler, E. Städler, В. Blattmann, H.R. Buser, N.U. Bosshard, L. Damm, M.W. Kozłowski, R. Schöni, R. Raschdorf, R. Dahinden, E. Schlumpf, H. Fritz, W.J. Richter, J. Schreiber, Experientia, 1987, 43, 157.
• [38] B. Ernst, B. Wagner, Helv. Chim. Acta, 1989, 72, 165.
• [39] T.A. van Beek, A. de Groot, Reel. Trav. Chim. Pays Bas, 1986, 105, 513.
• [40] S.V. Ley, P.L. Toogood, Chem. Brit., 1990, 26, 31.
• [41] S.V. Ley, D. Santafianos, W.M. Blaney, M.S.J. Simmonds, Tetrahedron Lett., 1987, 28, 221.
• [42] M. Eto, J.E. Casida, Progress and Prospects of Organophosphorus Agrochemicals, Kyushu University Press, Fukuoka 1995.
• [43] P.W. Lee, R. Allahyari, T.R. Fukuto, Pestic. Biochem. Physiol., 1978, 9, 23.
• [44] D.J. Armstrong, T.R. Fukuto, J. Agrie. Food Chem., 1987, 35, 500.
• [45] M. Ueji, C. Tomizawa, J. Pestic. Sci., 1987, 12, 269.
• [46] K. Wakabayashi, M. Hizue, H. Nozaki, M. Nakayama, N. Kurihara, J. Pestic. Sci, 1994, 19 277.
• [47] A.A. Nomeir, W.C. Dauterman, Pestic. Biochem. Physiol., 1979, 10, 121.
• [48] H. Ohkawa, N. Mikami, J. Miyamoto, Agric. Biol. Chem., 1977, 41, 369.
• [49] A. Hirashima, I. Ishaaya, R. Ueno, Y. Ichiyama, S.-Y. Wu, M. Eto, Agrie. Biol. Chem., 1989 53, 175.
• [50] N. Minowa, M. Hirayama, S. Fukatsu, Tetrahedron Letters, 1984, 1147.
• [51] A. Hirashima, I. Ishaaya, R. Ueno, Y. Ichiyama, S.-Y. Wu, M. Eto, Agrie. Biol. Chem., 1983, 47, 2831.
• [52] A. Miyazaki, T. Nakamura, M. Kawaradani, S. Marumo, J. Agrie. Food Chem., 1988, 36, 835.
• [53] H. Leader, J. E. Casida, J. Agrie. Food Chem., 1982, 30, 546.
• [54] J.J. Ellington, J.J. Evans, K.B. Prickett, W.L. Champion, J. Chrom. A, 2001, 928, 145.
• [55] M. Hutta, I. Rybar, M. Chalanyova, J. Chrom. A, 2002, 959, 143.
• [56] A. Jaus, M. Oehme, J. Chrom. A, 2001, 905, 59.
• [57] Y.S. Wu, H.K. Lee, S.F.Y. Li, J. Chrom. A, 2001, 912, 171.
• [58] A.K. Malik, W. Faubel, Crit. Rev. Anal. Chem., 2001, 31, 223.

Uwagi

PL

Opracowane ze środków MEiN, umowa nr SONP/SP/546092/2022 w ramach programu "Społeczna odpowiedzialność nauki" - moduł: Popularyzacja nauki i promocja sportu (2022-2023)