Mode of action of novel 2-(benzylamino)-4-methyl-6-(trifluoromethyl)- 1,3,5-triazine herbicides: Inhibition of photosynthetic electron transport and binding studies

Journal of Agricultural and Food Chemistry

Volumn 47, Issue 10, 1999, Pages 4398-4402

  Ohki, Aiko ^a   Kuboyama, Nobuhiro ^a   Koizumi, Kazuya ^b   Tanaka, Akira ^c   Sato, Yukiharu ^a   Kohno, Hitoshi ^a   Böger, Peter ^d   Wakabayashi, Ko ^a  

^a TAMAGAWA UNIVERSITY   (Japan)

^b Tomono Agrica Co Ltd   (Japan)

^c SHOWA PHARMACEUTICAL UNIVERSITY   (Japan)

^d UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

(Benzylamino) 1,3,5 triazines; Atrazine resistant Chenopodium; Binding partners; D1 protein; Replacement

Indexed keywords

ATRAZINE; HERBICIDE; TRIAZINE DERIVATIVE; VEGETABLE PROTEIN;

ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; DRUG EFFECT; ELECTRON TRANSPORT; GOOSEFOOT; METABOLISM; NONHUMAN; PHOTOSYNTHESIS; PROTEIN BINDING; SPINACH; THYLAKOID;

ELECTRON TRANSPORT; HERBICIDES; PHOTOSYNTHESIS; PLANT PROTEINS; PROTEIN BINDING; SPINACIA OLERACEA; TRIAZINES;

ACER PENSYLVANICUM; CHENOPODIUM; SPINACIA OLERACEA;

EID: 0033213663     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf990216o     Document Type: Article

References (21)

1. Arnon, D. I. Copper enzymes in isolated chloroplasts polyphenol-oxidase in Beta vulgaris. Plant Physiol. 1949, 24, 1-15.
2. Böger, P. Replacement of photosynthetic electron transport inhibitors by silicomolybdate. Physiol. Plant. 1982, 54, 221-224.
3. Böger, P. Inhibition of the photosynthetic electron transport system. In Target Assay for Modern Herbicides and Related Phytotoxic Compounds; Böger, P., Sandmann, G., Eds.; Lewis Publications: Boca Raton, FL, 1993; pp 83-91.
4. Gabbott, P. Progress in Photosynthesis Research; Metzner, H., Ed.; Verlag C. Lichtenstern: Munich, Germany, 1969; Vol. 3, pp 1712, 1969.
5. Gysin, H.; Knüsli, E. Swiss Patents 329,277, 342,784, and 342,-785 (to J. R. Geigy S.A.), 1954.
6. Hansch, C.; Fujita, T. A method for the correlation of biological activity and chemical structure. J. Am. Chem. Soc. 1964, 86, 1616-1626.
7. Hirschberg, J.; Bleeker, A; Kyle, D. J.; McIntosh, L.; Arntzen, C. J. The molecular basis of triazine herbicide resistance in higher-plant chloroplasts. Z. Naturforsch. 1984, 39C, 412-420.
8. Koizumi, K; Kuboyama, N.; Tomono, K.; Tanaka, A.; Ohki, A.; Kohno, H.; Böger, P.; Wakabayashi, K. Novel 1,3,5-triazine derivatives with herbicidal activity. In Book of Abstracts, 9th International Congress of Pesticide Chemistry; London, 1998; Vol. 1, 1C-001.
9. Kuboyama, N.; Koizumi, K.; Ohki, S.; Wakabayashi, K. Synthesis and herbicidal activity of 2-benzylamino-4-methyl-6-trifluoromethyl-1,3,5-triazine derivatives. J. Pestic. Sci. 1998, 23, 268-274.
10. Kuboyama, N.; Koizumi, K.; Ohki, A.; Ohki, S.; Kohno, H.; Wakabayashi, K. Photosynthetic electron transport inhibitory activity of 2-aralkylamino-4-methyl-6-trifluoromethyl-1,3,5-triazine derivatives. J. Pestic. Sci. 1999, 24, 138-142.
11. Morita, K.; Nagare, T.; Hayashi, Y. Quantitative structure-activity relationships for herbicidal 2-difluoromethylthio-4,6-bis(monoalkylamino)-1,3,5-triazines. Agric. Biol. Chem. 1987, 51, 1955-1957.
12. Ohki, A. The effect of photosynthetic electron transport inhibitors on peroxidizing mode of action of herbicides. Master's thesis, 1997.
13. Ohki, A.; Ohki, S.; Koizumi, K.; Sato, Y.; Kohno, H.; Böger, P.; Wakabayashi, K. Phytotoxicity caused by peroxidizing herbicides is alleviated by 2-substituted 4,6-bis(ethylamino)-1,3,5-triazines. J. Pestic. Sci. 1997, 22, 309-313.
14. 4-alkyl-2,4-diamino-6-chloro-s-triazines and their phytotoxic property. Agric. Biol. Chem. 1989, 53, 2723-2729.
15. Pfister, K.; Arntzen, C. J. The mode of action of photosystem II-specific inhibitors in herbicide-resistant weed biotypes. Z. Naturforsch. 1979, 34C, 996-1009.
16. Shimizu, R.; Iwamura, H.; Fujita, T. Quantitative structure-activity relationships of photosystem II inhibitory anilides and triazines. Topological aspects of their binding to the active site. J. Agric. Food Chem. 1988, 36, 1276-1283.
17. Siggel, U.; Renger, G.; Rumberg, B. In Proceedings of the 2nd International Congress on Photosynthesis Research; Junk Publishing: The Hague, The Netherlands, 197; Vol. 1, pp 753-762.
18. Sostic, M.; Sabljic, A. Inhibition of Hill reaction by 2-azido-s-triazine derivatives: QSAR study with molecular connectivity indices. Z. Naturforsch. 1989, 44C, 255-261.
19. Thiel, A.; Böger, P. Comparative herbicide binding by photosynthetic membranes from resistant mutants. Pestic. Biochem. Physiol. 1984, 22, 232-242.
20. Tischer, W.; Strotmann, H. Relationship between inhibitor binding by chloroplasts and inhibition of photosynthetic electron transport. Biochim. Biophys. Acta 1977, 460, 113-125.
21. Van Rensen, J. J. S.; Van derVet, W.; Van Vliet, W. P. A. Inhibition and uncoupling of electron transport in isolated chloroplasts by the herbicide 4,6-dinitro-o-cresol. Photochem. Photobiol. 1977, 25, 579-583.