title: Photosynthetic electron transport inhibition by pyrimidines and pyridines substituted with benzylamino, methyl and trifluoromethyl groups.
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.
authors.affiliation: Lehrstuhl für Physiologie und Biochemie der Pflanzen, Universität Konstanz, Germany.
authors.forename: S
authors.initials: S
authors.lastname: Ohki
authors.forename: H
authors.initials: H
authors.lastname: Takahashi
authors.forename: N
authors.initials: N
authors.lastname: Kuboyama
authors.forename: K
authors.initials: K
authors.lastname: Koizumi
authors.forename: H
authors.initials: H
authors.lastname: Kohno
authors.forename: J J
authors.initials: JJ
authors.lastname: van Rensen
authors.forename: K
authors.initials: K
authors.lastname: Wakabayashi
authors.forename: P
authors.initials: P
authors.lastname: Böger
mesh_terms: D001280:Atrazine / Q000494:pharmacology; D001593:Benzyl Compounds / Q000494:pharmacology; D019663:Chenopodiaceae / Q000187:drug effects / Q000378:metabolism*; D004579:Electron Transport / Q000187:drug effects; D010788:Photosynthesis / Q000187:drug effects / Q000502:physiology*; D011725:Pyridines / Q000494:pharmacology*; D011743:Pyrimidines / Q000494:pharmacology*; D018724:Spinacia oleracea / Q000378:metabolism*; D013329:Structure-Activity Relationship; D020524:Thylakoids / Q000187:drug effects / Q000378:metabolism*
chemical_list: D001593:Benzyl Compounds; D011725:Pyridines; D011743:Pyrimidines; D001280:Atrazine