Inhibition of plant growth by halogenated benzoic acids

Huffman, C. W.; Godar, Edith M.; Torgeson, Dewayne C.

doi:10.1021/jf60154a015

Cited by 7 publications

(5 citation statements)

References 6 publications

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“…Lastly, when introducing halogens (F, Cl or Br) in the para position, instead of a hydroxyl group (compounds 19, 20, and 21), an increase in bioactivity was observed, especially remarkable at the lowest concentrations, when compared with compound 6. A previous study showed the inhibiting activity of plant growth of the structurally related compound, benzoic acid (13), increased with the addition of halogen atoms in its aromatic ring [30]. Thus, it is interesting to highlight the role of the halogen substituents in phenyl rings, as also discussed in a previous review [31], and how parameters like stability are improved by factors such as the presence of a fluorine atom in the para-position [31].…”

Section: Discussionmentioning

confidence: 87%

Identification of Allelochemicals with Differential Modes of Phytotoxicity against Cuscuta campestris

et al. 2022

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Cuscuta campestris is a parasitic weed species with noxious effects in broadleaf crops worldwide. The control of Cuscuta in the majority of crops affected is limited or non-existing. We tested, for the first time, the effect of eighteen metabolites in in vitro-grown Cuscuta seedlings. We found that 2-benzoxazolinone, hydrocinnamic acid and pisatin caused the strongest inhibition of seedling growth. In addition to seedling growth, pisatin caused necrosis of the Cuscuta seedling, occurring mostly at the seedling shoot. Scopoletin and sesamol treatments caused toxicity, observed as a black staining, only at the Cuscuta root apices, while caffeic acid, ferulic acid and vanillic acid caused toxicity, observed as brown staining, in the root apices. The structure–activity relationships in four structural derivatives of 2-benzoxazolinone, and five structural derivatives of hydrocinnamic acid, were also studied. The identification of new herbicidal modes of action against Cuscuta is the first step in creating new alternatives to sustainable chemical control of parasitic weeds.

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Section: Discussionmentioning

confidence: 87%

Identification of Allelochemicals with Differential Modes of Phytotoxicity against Cuscuta campestris

et al. 2022

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“…To contextualize these results regarding the halogenation effects on the bioactivity, it can be highlighted that the phytotoxic activity of several halogenated derivatives of natural compounds has been known for some time. Halogenated derivatives of benzoic acid (weakly phytotoxic) with improved phytotoxicity were reported [ 26 , 27 ], as well as the finding of chlorinated and fluorinated derivatives of benzoxazinones with potent phytotoxicity [ 28 , 29 ]. These last studies described how the position of the halogen atom plays a key role in the level of phytotoxicity as a consequence of the marked electronic transformation of the tested compounds.…”

Section: Resultsmentioning

confidence: 99%

Identification of Structural Features of Hydrocinnamic Acid Related to Its Allelopathic Activity against the Parasitic Weed Cuscuta campestris

Moreno-Robles

Peralta

Zorrilla

et al. 2022

Plants

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Cuscuta campestris is a parasitic weed species that inflicts worldwide noxious effects in many broadleaf crops due to its capacity to withdraw nutrients and water directly from the crop vascular system using haustorial connections. Cuscuta campestris control in the majority of crops affected is non-existent, and thus, research for the development of control methods is needed. Hydrocinnamic acid occurs naturally in the rhizosphere, playing regulatory roles in plant–plant and plant–microbe communities. The toxicity of hydrocinnamic acid against C. campestris was recently identified. In the present work, a structure–activity relationship study of 21 hydrocinnamic acid analogues was performed to identify key structural features needed for its allelopathic action against the seedling growth of this parasitic plant. The findings of this study provide the first step for the design of herbicides with enhanced activity for the control of C. campestris infection.

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“…2-Chloro-5-iodobenzoic acid (6r). 39 The reaction was carried out according to the general procedure for 4-iodonitrobenzene (6a) using 5-amino-2-chlorobenzoic acid (5r) (0.050 g, 0.29 mmol), p-toluenesulfonic acid monohydrate (0.17 g, 0.87 mmol), polymer-supported nitrite (0.25 g, containing 0.87 mmol of NO 2 ) and sodium iodide (0.090 g, 0.58 mmol). The reaction mixture was stirred at room temperature for 24 h. This gave 2-chloro-5-iodobenzoic acid (6r) as a white solid (0.070 g, 79%).…”

Section: General Procedures For Preparation Of Polymer-supported Nitrimentioning

confidence: 99%

Late stage iodination of biologically active agents using a one-pot process from aryl amines

Sloan

Luthra²,

McRobbie³

et al. 2017

RSC Adv.

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Inhibition of plant growth by halogenated benzoic acids

Cited by 7 publications

References 6 publications

Identification of Allelochemicals with Differential Modes of Phytotoxicity against Cuscuta campestris

Identification of Allelochemicals with Differential Modes of Phytotoxicity against Cuscuta campestris

Identification of Structural Features of Hydrocinnamic Acid Related to Its Allelopathic Activity against the Parasitic Weed Cuscuta campestris

Late stage iodination of biologically active agents using a one-pot process from aryl amines

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