Substituted Tetrahydropyrimidinones: A New Herbicidal Class of Compounds Inducing Chlorosis by Inhibition of Phytoene Desaturation

Babczinski, Peter; Blunck, M.; Sandmann, Gerhard; Shiokawa, Kohzoh; Yasui, Koji

doi:10.1006/pest.1995.1029

Cited by 22 publications

(4 citation statements)

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“…There are many matched pairs of compounds known, which possess an almost identical molecular structure, only differing in a heterocyclic ring. Furanone of phytoene-desaturase-inhibiting bleaching herbicide fluridone ( 33 ) is perfectly mimicked by furanone of flurtamone ( 32 ) and by cyclic urea of NTN-28621 ( 34 ). , The fungicidal activity of boscalid ( 35 ) could be significantly improved by replacing its pyridine ring in its acid portion by pyrazole, which delivers fluxapyroxad ( 36 ). Recently, it was shown that also pyrazine is tolerated in this position because novel fungicide pyraziflumid ( 37 ) has been announced.…”

Section: Replacement Of a Heterocycle By Another Heterocyclic Ringmentioning

confidence: 99%

Isosteric Ring Exchange as a Useful Scaffold Hopping Tool in Agrochemistry

Lamberth

2023

J. Agric. Food Chem.

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Replacing one ring in a molecule by a different carba- or heterocycle is an important scaffold hopping manipulation, because biologically active compounds and their analogues, which underwent such a transformation, are often similar in size, shape, and physicochemical properties and, therefore, likely in their potency as well. This review will demonstrate, how isosteric ring exchange led to the discovery of highly active agrochemicals and which ring interchanges have proven to be most successful.

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Section: Replacement Of a Heterocycle By Another Heterocyclic Ringmentioning

confidence: 99%

Isosteric Ring Exchange as a Useful Scaffold Hopping Tool in Agrochemistry

Lamberth

2023

J. Agric. Food Chem.

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“…Since phytoene desaturase (PDS) catalyzes dehydrogenation of phytoene to zeta carotene which protects chlorophyll from photo oxidation [1][2][3][4], it has been a well-known major target enzyme of herbicides in the cartenoid biosynthesis pathway and has attracted considerable attention. Up to now, many novel compounds (e.g., 2,6-diphenylpyridines [5,6], phenoxypyridincarbonamides [7,8], diarylpyrimidines [9,10], 1,1'-biphenyl derivatives [11], tetrahydropyrimidinones [12,13], phenylpyrimidinones [14], and diphenylpyrrolidinones [15]) have been identified as phytoene desaturase inhibitors and commercialized.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and herbicidal activities of novel 4-(3-trifluoromethylphenyl)-2H-pyridazin-3-one derivatives

Xiao

Zhu

et al. 2010

Sci. China Chem.

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“…Mitchell () proposed a model of the herbicidal binding site of PDS using superimposition with five structurally different inhibitors. Although structure−activity relationship (SAR) studies have been carried out ( , ), it is still not known which structural elements of the inhibitors are essential for potent PDS inhibition. In the long run, such an SAR study should be performed using PDS inhibitors belonging to different chemical classes and the PDS inhibitory data of the compounds obtained by a cell-free assay.…”

Section: Introductionmentioning

confidence: 99%

Phytoene Desaturase Inhibition by O-(2-Phenoxy)ethyl-N-aralkylcarbamates

Ohki

Miller-Sulger

Wakabayashi

et al. 2003

J. Agric. Food Chem.

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O-[1-Ethyl-2-(3-trifluoromethylphenoxy)]ethyl-N-benzylcarbamate exhibits a marked inhibition of carotenoid biosynthesis. Forty-one analogues were synthesized and assayed for plant-type phytoene desaturase (PDS) and zeta-carotene desaturase (ZDS) inhibition in a cell-free system using recombinant enzymes obtained from Escherichia coli transformants. The target enzyme of all carbamates synthesized in this study is PDS and not ZDS; no inhibition of ZDS was observed using a 10(-4) M inhibitor concentration. Four compounds, O-[1-ethyl-2-(3-trifluoromethylphenoxy)]ethyl-N-(2-phenylethyl)carbamate (23), O-[1-ethyl-2-(3-trifluoromethylphenoxy)]ethyl-N-(2-chlorobenzyl)carbamate (25), O-[1-ethyl-2-(3-trifluoromethylphenoxy)]ethyl-N-(2-chlorobenzyl)carbamate (26), and O-[1-methyl-2-(3-trifluoromethylphenoxy)]ethyl-N-benzylcarbamate (30), were the most potent PDS inhibitors. Their pI(50) values, the negative logarithms of the molar concentration that produces a 50% inhibition, were 7.5, representing the same inhibitory activity as norflurazon. With respect to a structure-activity relationship the oxygen atom of the phenoxy group and a carbamate structure in O-(1-ethyl-2-phenoxy)ethyl-N-aralkylcarbamates studied were found to be essential for strong PDS inhibitors. Also, introduction of an ethyl group at the alpha-position of the ethylene bridge between the phenoxy group and the carbamate was important for a strong PDS inhibitor. Substituents at the 2- and/or 3-position of the phenoxybenzene ring were found to be favorable to a strong PDS inhibition of the analogues.

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Substituted Tetrahydropyrimidinones: A New Herbicidal Class of Compounds Inducing Chlorosis by Inhibition of Phytoene Desaturation

Cited by 22 publications

References 0 publications

Isosteric Ring Exchange as a Useful Scaffold Hopping Tool in Agrochemistry

Isosteric Ring Exchange as a Useful Scaffold Hopping Tool in Agrochemistry

Synthesis and herbicidal activities of novel 4-(3-trifluoromethylphenyl)-2H-pyridazin-3-one derivatives

Phytoene Desaturase Inhibition by O-(2-Phenoxy)ethyl-N-aralkylcarbamates

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