Synthesis and inhibitory effect on photosynthetic electron transport of 1,3,5-triazinylcarboxylic acid derivatives

A. Fujimori, Y. Ikeda, R. Okano, M. Hiraki, J.J.S. van Rensen, P. Boger, H. Kohno, K. Wakabayashi

Research output: Contribution to journalArticleAcademicpeer-review

1 Citation (Scopus)

Abstract

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 atrazine-resistant 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 pI50 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. © Presticide Science Society of Japan
Original languageEnglish
Pages (from-to)39-43
JournalJournal of Pesticide Science
Volume30
Issue number1
DOIs
Publication statusPublished - 2005

Fingerprint

Triazines
triazines
Electron Transport
electron transfer
chemical derivatives
Acids
synthesis
acids
Chenopodium album
Atrazine
Thylakoids
Spinacia oleracea
atrazine
spinach
thylakoids
Japan
Esters
esters
electrons
Electrons

Keywords

  • chenopodium-album
  • resistant

Cite this

Fujimori, A., Ikeda, Y., Okano, R., Hiraki, M., van Rensen, J. J. S., Boger, P., ... Wakabayashi, K. (2005). Synthesis and inhibitory effect on photosynthetic electron transport of 1,3,5-triazinylcarboxylic acid derivatives. Journal of Pesticide Science, 30(1), 39-43. https://doi.org/10.1584/jpestics.30.39
Fujimori, A. ; Ikeda, Y. ; Okano, R. ; Hiraki, M. ; van Rensen, J.J.S. ; Boger, P. ; Kohno, H. ; Wakabayashi, K. / Synthesis and inhibitory effect on photosynthetic electron transport of 1,3,5-triazinylcarboxylic acid derivatives. In: Journal of Pesticide Science. 2005 ; Vol. 30, No. 1. pp. 39-43.
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abstract = "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 atrazine-resistant 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 pI50 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. {\circledC} Presticide Science Society of Japan",
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Fujimori, A, Ikeda, Y, Okano, R, Hiraki, M, van Rensen, JJS, Boger, P, Kohno, H & Wakabayashi, K 2005, 'Synthesis and inhibitory effect on photosynthetic electron transport of 1,3,5-triazinylcarboxylic acid derivatives' Journal of Pesticide Science, vol. 30, no. 1, pp. 39-43. https://doi.org/10.1584/jpestics.30.39

Synthesis and inhibitory effect on photosynthetic electron transport of 1,3,5-triazinylcarboxylic acid derivatives. / Fujimori, A.; Ikeda, Y.; Okano, R.; Hiraki, M.; van Rensen, J.J.S.; Boger, P.; Kohno, H.; Wakabayashi, K.

In: Journal of Pesticide Science, Vol. 30, No. 1, 2005, p. 39-43.

Research output: Contribution to journalArticleAcademicpeer-review

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T1 - Synthesis and inhibitory effect on photosynthetic electron transport of 1,3,5-triazinylcarboxylic acid derivatives

AU - Fujimori, A.

AU - Ikeda, Y.

AU - Okano, R.

AU - Hiraki, M.

AU - van Rensen, J.J.S.

AU - Boger, P.

AU - Kohno, H.

AU - Wakabayashi, K.

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N2 - 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 atrazine-resistant 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 pI50 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. © Presticide Science Society of Japan

AB - 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 atrazine-resistant 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 pI50 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. © Presticide Science Society of Japan

KW - chenopodium-album

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