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BY-NC-ND 3.0 license Open Access Published by De Gruyter June 2, 2014

Photosynthetic Electron Transport Inhibition by Pyrimidines and Pyridines Substituted with Benzylamino, Methyl and Trifluoromethyl Groups

  • Shinpei Ohki , Hideomi Takahashi , Nobuhiro Kuboyama , Kazuya Koizumi , Hitoshi Kohno , Jack J. S. van Rensen , Ko Wakabayashi and Peter Böger

Abstract

The decrease of the number of ring nitrogen atoms of 2-benzylamino-4-methyl-6-trifluoro-methyl-1,3,5-triazines on herbicidal activity and inhibition of photosynthetic electron trans­ port (PET) was assayed using thylakoids from Spinacia oleracea or atrazine-resistant Chenopodium album. Three 2-benzylamino-4-methyl-6-trifluoromethyl-1,3,5-triazines, nine pyrimidines with a benzylamino-, methyl-and trifluoromethyl-group, 2-benzylamino-6-methyl-4-trifluoromethyl-pyridine and N-benzyl-3-methyl-5-trifluoromethylaniline were synthesized and assayed. 2-(4-Bromobenzylamino)-4-methyl-6-trifluoromethylpyrimidine exhibited the highest PET inhibitory activity against Spinacia oleracea thylakoids of all compounds tested. The 2-benzylaminopyrimidines and 2-methylpyrimidines having a 4-halobenzylamino group exhibited higher PET inhibition than atrazine and 2-trifluoromethylpyrimidines against Spinacia oleracea thylakoids. These PET inhibitory active compounds also exhibited a strong and similar inhibition both against atrazine-resistant Chenopodium album thylakoids as well as against thylakoids from wild-type Chenopodium. The herbicidal activity of 4-(4-bromoben-zylamino)-2-methyl-6-trifluoromethylpyrimidine was equivalent to that of known herbicides like simetryne, simazine or atrazine.

Received: 2001-1-22
Published Online: 2014-6-2
Published in Print: 2001-4-1

© 1946 – 2014: Verlag der Zeitschrift für Naturforschung

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

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