Photosynthetic electron transport inhibition by pyrimidines and pyridines substituted with benzylamino, methyl and trifluoromethyl groups

S. Ohki, H. Takahashi, N. Kuboyama, K. Koizumi, H. Kohno, J.J.S. van Rensen, K. Wakabayashi, P. Böger

Research output: Contribution to journalArticleAcademicpeer-review

2 Citations (Scopus)

Abstract

The decrease of the number of ring nitrogen atoms of 2-benzylamino-4-methyl-6-trifluoromethyl-1,3,5-triazines on herbicidal activity and inhibition of photosynthetic electron transport (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-bromobenzylamino)-2-methyl-6-trifluoromethylpyrimidine was equivalent to that of known herbicides like simetryne, simazine or atrazine.
Original languageEnglish
Pages (from-to)203-210
JournalZeitschrift für Naturforschung. Section C : a Journal of Biosciences
Volume56c
Publication statusPublished - 2001

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