Synthesis and Herbicidal Activity of 2-Benzylamino-4-methyl-6-trifluoromethyl-1, 3, 5-triazune Derivatives

Kuboyama, Nobuhiro; Koizumi, Kazuya; Ohki, Shinpei; Wakabayashi, Katsunori

doi:10.1584/jpestics.23.268

Cited by 11 publications

(13 citation statements)

References 3 publications

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“…Photosynthetic electron transport (PET) inhibitory activity and herbicidal activity of 2-benzylamino-4methyl-6-trifluoromethyl-1, 3, 5-triazines have already been reported by Kuboyama et a1. 1,2) in our group. Some of these compounds showed relatively strong activities and especially 2-(4-chloro or 4-bromobenzylamino)-4-methyl-6-trifluoromethyl-1, 3, 5-triazines exhibited much stronger herbicidal activity and more potent PET inhibition than simazine.…”

Section: Introductionmentioning

confidence: 53%

Photosynthetic Electron Transport Inhibitory and Herbicidal Activities of 2-(Fluorinated methyl-4-benzylamino-6-methyl)-1, 3, 5-triazines

et al. 2000

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To investigate the substitution effect of the fluorine atom on methyl group, a methyl group of 2-benzylamino-4, 6-dimethyl-1, 3, 5-triazines was replaced with fluoromethyl, difluoromethyl and trifluoromethyl groups and photosynthetic electron transport (PET) inhibitory and herbicidal activities of these (fluorinated methyl)-1, 3, 5-triazine compounds were evaluated. With increasing the number of fluorine atom of fluorinated methyl group, PET inhibitory activity became higher. Furthermore by introduction of a halogen atom to the 4-position of the benzyl group, PET inhibitory activity was much improved compared to the triazines having an un-substituted benzylamino group. The (fluorinated methyl)-1, 3, 5-triazine derivatives with higher PET inhibitory activity showed also stronger herbicidal activity in soil and foliar application tests.

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Section: Introductionmentioning

confidence: 53%

Photosynthetic Electron Transport Inhibitory and Herbicidal Activities of 2-(Fluorinated methyl-4-benzylamino-6-methyl)-1, 3, 5-triazines

et al. 2000

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“…11,12) Among the derivatives with an amino group, 2-ethoxycarbonyl-4- Note: Physical data for compounds 10-12 were reported by Kuboyama et al 11) and Inoue et al 12) Melting points (uncorrected) were measured with a Yanagimoto-Seisakusyo melting point apparatus. IR were recorded on a JASCO FT/IR-420 spectrophotometer.…”

Section: Pet Inhibitory Activity Of 2-amino-4-methyl-135-triazinylcmentioning

confidence: 99%

Synthesis and Inhibitory Effect on Photosynthetic Electron Transport of 1,3,5-Triazinylcarboxylic Acid Derivatives

et al. 2005

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This study relates to the modification of 2-benzylamino-4-methyl-6-trifluoromethyl-1,3,5-triazine. New 1,3,5-triazine compounds with an electron-withdrawing carboxyl group, e.g. ester group, substituted for the trifluoromethyl group, were synthesized and assayed for activity to inhibit photosynthetic electron transport (PET) in thylakoids of spinach as well as both atrazineresistant and wild-type Chenopodium album. Among the compounds with an alkylamino group, 2-ethoxycarbonyl-4-isopropylamino-6-methyl-1,3,5-triazine was the most potent PET-inhibitor, exhibiting a pI 50 of 6.11. The inhibitory activity was generally more potent with 2-alkoxycarbonyl-4-(branched alkyl)amino-6-methyl-1,3,5-triazines than amino-analogues with straight chain alkyl groups or unsaturated alkyl groups.

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“…IR-spectra were recorded on a JASCO FT/IR-420 spectrophotom eter and NM R spectra m easured in CDC13 on a JE O L JNM-GX400 FT-NMR (400 Hz). The spectroscopical data of 2-benzylamino-4-methyl-6-trifluoromethyl-l,3,5-triazines (1 -3 ) are shown in our previous papers (Kuboyama et al, 1998;Kuboyama et al, 1999). Spectroscopical data of compounds (4-15) are docum ented in Sec tion below.…”

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confidence: 95%

“…Previously, we have reported on the herbicidal activity of novel 2-benzylamino-l,3,5-triazines (Kuboyama et al, 1998). In our synthetic and bio assay programs, 2-benzylamino-4-methyl-6-trifluoromethyl-l,3,5-triazines, e.g.…”

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confidence: 99%

“…Especially they have been found to exhibit a strong PET inhibition against both wildtype and atrazine-resistant thylakoids from Che nopodium album (Kohno et al, 2000). 0939 Chemicals 2-Benzylamino-4-methyl-6-trifluoromethyl-1,3,5-triazines (1-3) were prepared according to Kuboyama et al (1998;1999). The pyrimidines (4-12) were obtained by a nucleophilic replacement reaction of the corresponding chloropyrimidines with corresponding benzylamines.…”

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

Ohki

Takahashi

Kuboyama³

et al. 2001

Zeitschrift Für Naturforschung C

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PET Inhibitory Activity, Atrazine-Resistant Chenopodium album , 4-Benzylamino-2-methyl-6-trifluoromethylpyrimidines The decrease of the num ber of ring nitrogen atoms of 2-benzylamino-4-methyl-6-trifluoromethyl-l,3,5-triazines on herbicidal activity and inhibition of photosynthetic electron trans port (PET) was assayed using thylakoids from Spinacia oleracea or atrazine-resistant Cheno podium album. Three 2-benzylamino-4-methyl-6-trifluoromethyl-l,3,5-triazines, nine pyrimi dines with a benzylamino-, methyl-and trifluoromethyl-group, 2-benzylamino-6-methyl-4-trifluoromethyl-pyridine and N-benzyl-S-methyl-S-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 Spi nacia 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.

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Synthesis and Herbicidal Activity of 2-Benzylamino-4-methyl-6-trifluoromethyl-1, 3, 5-triazune Derivatives

Cited by 11 publications

References 3 publications

Photosynthetic Electron Transport Inhibitory and Herbicidal Activities of 2-(Fluorinated methyl-4-benzylamino-6-methyl)-1, 3, 5-triazines

Photosynthetic Electron Transport Inhibitory and Herbicidal Activities of 2-(Fluorinated methyl-4-benzylamino-6-methyl)-1, 3, 5-triazines

Synthesis and Inhibitory Effect on Photosynthetic Electron Transport of 1,3,5-Triazinylcarboxylic Acid Derivatives

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

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