Synthetic Plant-Growth Modifiers. IV. 2-Methyl-4-Chlorophenoxyacetyl Derivatives of Amino Acids

Krewson, C. F.; Neufeld, C. H. H.; Drake, T. F.; Fontaine, Thomas D.; Mitchell, John W.; join(, W. H. Preston

doi:10.2307/4040127

Cited by 12 publications

(16 citation statements)

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“…The low activities of l-and DL-phenylalanine and the moderate action of land DL-methionine derivatives of 2,4-DP on all plants were in sharp contrast to the high activities of the corresponding land DL-amino acid derivatives of 2,4-D (70), 2-methyl-4-chloro- (7), and 4chlorophenoxvacetic acid (6) derivatives.…”

Section: Results Of Plant Screeningmentioning

confidence: 81%

“…For the preparation of amino acid derivatives of 2,4-DP, procedures similar to those previously described (7) were employed. The amino acids used in this work were the best obtainable through commercial sources.…”

Section: Methodsmentioning

confidence: 99%

“…The solvent combinations required are indicated in the footnotes in Table I. curvature, epinasty, cellular proliferation, formative effects, and suppression of vegetative growth at 2, 4, 6, and 14 days (7).…”

Section: Methodsmentioning

confidence: 99%

“…The lanolin assay method (7) was used on the dicots and the coated sand assay method (7) was used on the monocots.…”

Section: Preliminary Screeningmentioning

confidence: 99%

“…However, the percentage of plants killed at the concentration level used is reported as a matter of preliminary interest. Scores covering the second, fourth, sixth, and fourteenth day observations for the various responses to treatment with each d-, l-, and DL-amino acid compound were added and expressed as a percentage of the maximum response possible in the same manner as in a preceding paper (7). Again, because of the voluminous nature of these data, the complete tabulation does not appear in this paper.…”

Section: Preliminary Screeningmentioning

confidence: 99%

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Plant Growth Regulators, Preliminary Screening Tests of Amino Acid Derivatives of 2-(2',4'-Dichlorophenoxy)propionic Acid

Krewson¹,

Drake²,

Mitchell³

et al. 1956

J. Agric. Food Chem.

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Because the optical configuration of compounds affecting plant growth is important to their selectivity, a series of new amino acid derivatives of 2-(2',4'-dich1orophenoxy)-propionic acid in their D-, 1-, and DL-forms has been synthesized and screened for effectiveness as plant-growth regulators. This investigation was undertaken specifically to widen the possibilities for utilization of amino acids, and in general to elucidate the mode of action of growth regulators. The derivatives of DL-and L-amino acids proved generally to be active plant-growth regulators with high selectivity; those of the D-amino acids were almost completely lacking in growth-regulating properties during the test period. A variety of notable differences in behavior patterns are characteristic of this series, in sharp contrast to generalities reported for other halogenated phenoxy acid series. These derivatives are easily prepared and analyzed, and possess sharp melting points; hence they may be useful in the characterization of amino acids.

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Section: Results Of Plant Screeningmentioning

confidence: 81%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

“…The lanolin assay method (7) was used on the dicots and the coated sand assay method (7) was used on the monocots.…”

Section: Preliminary Screeningmentioning

confidence: 99%

Section: Preliminary Screeningmentioning

confidence: 99%

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Plant Growth Regulators, Preliminary Screening Tests of Amino Acid Derivatives of 2-(2',4'-Dichlorophenoxy)propionic Acid

Krewson¹,

Drake²,

Mitchell³

et al. 1956

J. Agric. Food Chem.

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The Design of Auxin-Type Herbicides

Garraway¹,

Wain²

1976

Drug Design

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Identification of a Novel 2,4-D Metabolic Detoxification Pathway in 2,4-D-Resistant Waterhemp (Amaranthus tuberculatus)

Figueiredo

Barnes

Boot

et al. 2022

J. Agric. Food Chem.

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A 2,4-dichlorophenoxyactic acid (2,4-D)-resistant population of Amaranthus tuberculatus (common waterhemp) from Nebraska, USA, was previously found to have rapid metabolic detoxification of the synthetic auxin herbicide 2,4-D. We purified the main 2,4-D metabolites from resistant and susceptible plants, solved their structures by nuclear magnetic resonance (NMR) and high-resolution mass spectrometry (HRMS), and synthesized the metabolites to determine their in planta toxicity. Susceptible plants conjugated 2,4-D to aspartate to form 2,4-D-aspartic acid (2,4-D-Asp), while resistant plants had a unique metabolic profile where 2,4-D was hydroxylated into 5-OH-2,4-D, followed by conjugation into a sugar metabolite (2,4-D-5-O-d-glucopyranoside) and subsequent malonylation into 2,4-D-(6′-O-malonyl)-5-O-d-glucopyranoside. Toxicological studies on waterhemp and Arabidopsis thaliana confirmed that the hydroxylated metabolite lost its auxinic action and toxicity. In contrast, the 2,4-D-Asp metabolite found in susceptible plants retained some auxinic action and toxicity. These results demonstrate that 2,4-D-resistant A. tuberculatus evolved novel detoxification reactions not present in susceptible plants to rapidly metabolize 2,4-D, potentially mediated by cytochrome P450 enzymes that perform the initial 5-hydroxylation reaction. This novel mechanism is more efficient to detoxify 2,4-D and produces metabolites with lower toxicity compared to the aspartic acid conjugation found in susceptible waterhemp.

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Synthetic Plant-Growth Modifiers. IV. 2-Methyl-4-Chlorophenoxyacetyl Derivatives of Amino Acids

Cited by 12 publications

References 0 publications

Plant Growth Regulators, Preliminary Screening Tests of Amino Acid Derivatives of 2-(2',4'-Dichlorophenoxy)propionic Acid

Plant Growth Regulators, Preliminary Screening Tests of Amino Acid Derivatives of 2-(2',4'-Dichlorophenoxy)propionic Acid

The Design of Auxin-Type Herbicides

Identification of a Novel 2,4-D Metabolic Detoxification Pathway in 2,4-D-Resistant Waterhemp (Amaranthus tuberculatus)

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