Synthesis and Herbicidal Activity of New Hydrazide and Hydrazonoyl Derivatives

František Šeršeň; Fridrich Gregáň; Matúš Peško; Dana Dvoranová; Katarína Kráľová; Zuzana Matkovičová; Juraj Gregan; Jana Donovalová

doi:10.3390/molecules200814139

Synthesis and Herbicidal Activity of New Hydrazide and Hydrazonoyl Derivatives

František Šeršeň, Fridrich Gregáň, Matúš Peško, Dana Dvoranová, Katarína Kráľová, Zuzana Matkovičová, Juraj Gregan, Jana Donovalová

Publications: Contribution to journal › Article › Peer Reviewed

Abstract

Three new hydrazide and five new hydrazonoyl derivatives were synthesized. The chemical structures of these compounds were confirmed by 1H-NMR, IR spectroscopy and elemental analysis. The prepared compounds were tested for their activity to inhibit photosynthetic electron transport in spinach chloroplasts and growth of the green algae Chlorella vulgaris. IC50 values of these compounds varied in wide range, from a strong to no inhibitory effect. EPR spectroscopy showed that the active compounds interfered with intermediates Z•/D•, which are localized on the donor side of photosystem II. Fluorescence spectroscopy suggested that the mechanism of inhibitory action of the prepared compounds possibly involves interactions with aromatic amino acids present in photosynthetic proteins.

Original language	English
Pages (from-to)	14139-14154
Number of pages	16
Journal	Molecules
Volume	20
Issue number	8
DOIs	https://doi.org/10.3390/molecules200814139
Publication status	Published - 4 Aug 2015

Austrian Fields of Science 2012

106002 Biochemistry
106023 Molecular biology

Keywords

Chlorella
Chloroplasts
Electron Spin Resonance Spectroscopy
Electron Transport
Herbicides
Hydrazines
Hydrazones
Inhibitory Concentration 50
Photosynthesis
Spectrometry, Fluorescence
Spinacia oleracea
Journal Article
Research Support, Non-U.S. Gov't
N′-[2,6-dinitro-4-[trifluoromethyl)phenyl]hydrazonoyl derivatives
Spinach chloroplasts
Green algae
N′-[2,6-dinitro-4-(trifluoromethyl)phenyl]hydrazides
Photosynthesis inhibition

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title = "Synthesis and Herbicidal Activity of New Hydrazide and Hydrazonoyl Derivatives",

abstract = "Three new hydrazide and five new hydrazonoyl derivatives were synthesized. The chemical structures of these compounds were confirmed by 1H-NMR, IR spectroscopy and elemental analysis. The prepared compounds were tested for their activity to inhibit photosynthetic electron transport in spinach chloroplasts and growth of the green algae Chlorella vulgaris. IC50 values of these compounds varied in wide range, from a strong to no inhibitory effect. EPR spectroscopy showed that the active compounds interfered with intermediates Z•/D•, which are localized on the donor side of photosystem II. Fluorescence spectroscopy suggested that the mechanism of inhibitory action of the prepared compounds possibly involves interactions with aromatic amino acids present in photosynthetic proteins.",

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author = "Franti{\v s}ek {\v S}er{\v s}e{\v n} and Fridrich Greg{\'a}{\v n} and Mat{\'u}{\v s} Pe{\v s}ko and Dana Dvoranov{\'a} and Katar{\'i}na Kr{\'a}{\v I}ov{\'a} and Zuzana Matkovi{\v c}ov{\'a} and Juraj Gregan and Jana Donovalov{\'a}",

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doi = "10.3390/molecules200814139",

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AU - Šeršeň, František

AU - Gregáň, Fridrich

AU - Peško, Matúš

AU - Dvoranová, Dana

AU - Kráľová, Katarína

AU - Matkovičová, Zuzana

AU - Gregan, Juraj

AU - Donovalová, Jana

PY - 2015/8/4

Y1 - 2015/8/4

N2 - Three new hydrazide and five new hydrazonoyl derivatives were synthesized. The chemical structures of these compounds were confirmed by 1H-NMR, IR spectroscopy and elemental analysis. The prepared compounds were tested for their activity to inhibit photosynthetic electron transport in spinach chloroplasts and growth of the green algae Chlorella vulgaris. IC50 values of these compounds varied in wide range, from a strong to no inhibitory effect. EPR spectroscopy showed that the active compounds interfered with intermediates Z•/D•, which are localized on the donor side of photosystem II. Fluorescence spectroscopy suggested that the mechanism of inhibitory action of the prepared compounds possibly involves interactions with aromatic amino acids present in photosynthetic proteins.

AB - Three new hydrazide and five new hydrazonoyl derivatives were synthesized. The chemical structures of these compounds were confirmed by 1H-NMR, IR spectroscopy and elemental analysis. The prepared compounds were tested for their activity to inhibit photosynthetic electron transport in spinach chloroplasts and growth of the green algae Chlorella vulgaris. IC50 values of these compounds varied in wide range, from a strong to no inhibitory effect. EPR spectroscopy showed that the active compounds interfered with intermediates Z•/D•, which are localized on the donor side of photosystem II. Fluorescence spectroscopy suggested that the mechanism of inhibitory action of the prepared compounds possibly involves interactions with aromatic amino acids present in photosynthetic proteins.

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KW - Chloroplasts

KW - Electron Spin Resonance Spectroscopy

KW - Electron Transport

KW - Herbicides

KW - Hydrazines

KW - Hydrazones

KW - Inhibitory Concentration 50

KW - Photosynthesis

KW - Spectrometry, Fluorescence

KW - Spinacia oleracea

KW - Journal Article

KW - Research Support, Non-U.S. Gov't

KW - N′-[2,6-dinitro-4-[trifluoromethyl)phenyl]hydrazonoyl derivatives

KW - Spinach chloroplasts

KW - Green algae

KW - N′-[2,6-dinitro-4-(trifluoromethyl)phenyl]hydrazides

KW - Photosynthesis inhibition

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U2 - 10.3390/molecules200814139

DO - 10.3390/molecules200814139

M3 - Article

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SN - 1420-3049

VL - 20

SP - 14139

EP - 14154

JO - Molecules

JF - Molecules

IS - 8

ER -

Synthesis and Herbicidal Activity of New Hydrazide and Hydrazonoyl Derivatives

Abstract

Austrian Fields of Science 2012

Keywords

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