Photosynthetic Electron Transport Inhibitory Activity of 2-Aralkylamino-4-methyl-6-trifluoromethyl-1, 3, 5-triazine Derivatives

Abstract

A series of 2-aralkylamino-1, 3, 5-triazine derivatives was synthesized and their photosynthetic electron transport (PET) inhibitory activity was evaluated. Investigation on the relationship between PET inhibitory activity and substituents on the triazine ring revealed that 2-benzylamino-4-methyl-6-trifluoromethyl-1, 3, 5-triazine exhibited a highly PET inhibitory activity. Furthermore, introduction of a halogen or a trifluoromethyl group at 3- or 4-position of the benzene ring enhanced PET inhibitory activity, exhibiting pI₅₀=6.91-7.29. Their PET inhibition was about 10 times stronger than that of simazine. On the absolute configuration of chiral center in 2-methyl-4-(α-methylbenzylamino)6-trifluoromethyl-1, 3, 5-triazine, (-)-enantiomer was around 100 times stronger than (+)- enantiomer. However, the PET inhibitory activity was decreased by N-alkylation of the benzylamino group in 2-benzylamino-4-methyl-6-trifluoromethyl-1, 3, 5-triazine.