Synthesis and herbicidal activity of novel 2,3‐dibromo‐5‐ trifluoromethyl‐4‐pyrrolecarboxylate derivatives

Bauer, Klaus; Hoffmann, Michael

doi:10.1002/ps.2780420105

Cited by 6 publications

(1 citation statement)

References 5 publications

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“…From the above results, the most active synthetic chalcones generally contained phenoxyacetic acid, 4-( N , N -dimethylamino)phenyl, N -methylpyrrole, or thiophenyl rings. Some herbicides bearing similar functional groups have been reported previously, for example, phenoxy, aminobenzene, pyrrole, and thiophene herbicides. Even though we should not speculate that the herbicidal potential and the mode of action of any compounds depend purely on a single functional group, these structures are still worth mentioning in order to understand a relationship between substituents and a trend of activity of those compounds.…”

Section: Resultsmentioning

confidence: 64%

Herbicidal Activity of Flavokawains and Related trans-Chalcones against Amaranthus tricolor L. and Echinochloa crus-galli (L.) Beauv.

2019

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Flavokawains have a broad spectrum of biological activities; however, the herbicidal activity of these naturally occurring chalcones has been less investigated. Flavokawains and their analogues were prepared by the Claisen–Schmidt condensation reaction between xanthoxyline (or aromatic ketones) and a variety of aromatic and heteroaromatic aldehydes. These compounds were then evaluated for their inhibitory effect against representative dicot and monocot plants. Among 45 synthetic chalcones, derivatives containing phenoxyacetic acid, 4-(N,N-dimethylamino)phenyl, N-methylpyrrole, or thiophenyl groups inhibited the germination and growth of Chinese amaranth (Amaranthus tricolor L.) with moderate to high degrees compared to commercial butachlor. For barnyardgrass (Echinochloa crus-galli (L.) Beauv.), most of the thiophenyl chalcones interrupted shoot and root emergence. This finding highlighted the importance of functional groups on the herbicidal activity of chalcones. The level of inhibition also depended on the applied concentrations, plant species, and plant organs. (E)-2-(2-(3-Oxo-3-(thiophen-2-yl)prop-1-enyl)phenoxy)acetic acid (14f) was the most active compound among 45 derivatives. This chalcone could be a promising structure for controlling the germination and growth of weeds. The structure–activity relationship results provide useful information about the development of active chalconoids as novel natural product-like herbicides.

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Section: Resultsmentioning

confidence: 64%

Herbicidal Activity of Flavokawains and Related trans-Chalcones against Amaranthus tricolor L. and Echinochloa crus-galli (L.) Beauv.

2019

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Functionalization of 2‐Trifluoromethyl‐1H‐pyrrole: A Convenient Entry into Advanced Fluorinated Building Blocks Including all Isomeric 2‐(Trifluoromethyl)prolines

et al. 2020

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The synthetic utility of 2‐trifluoromethyl‐1H‐pyrrole as a pharmaceutically relevant platform was demonstrated by the preparation of mono‐ and bifunctional C‐2(5)‐ or C‐3‐substituted derivatives, i.e. regioisomeric sulfonyl halides, carboxylic acids, aldehydes, and nitriles. A series of modifications relied on lithiation or electrophilic substitution, which proceeded regioselectively on multigram scale, mostly in protecting‐group‐free mode. Subsequent catalytic hydrogenation of the pyrrole ring was also performed for synthesis of all isomeric 2‐trifluoromethyl α‐ and β‐prolines. These derivatives were considered as promising low‐molecular‐weight building blocks for synthesis, drug discovery, and agrochemistry.

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Pyrroles and their Benzo Derivatives: Applications

Gribble

1996

Comprehensive Heterocyclic Chemistry II

110

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Synthesis and herbicidal activity of novel 2,3‐dibromo‐5‐ trifluoromethyl‐4‐pyrrolecarboxylate derivatives

Cited by 6 publications

References 5 publications

Herbicidal Activity of Flavokawains and Related trans-Chalcones against Amaranthus tricolor L. and Echinochloa crus-galli (L.) Beauv.

Herbicidal Activity of Flavokawains and Related trans-Chalcones against Amaranthus tricolor L. and Echinochloa crus-galli (L.) Beauv.

Functionalization of 2‐Trifluoromethyl‐1H‐pyrrole: A Convenient Entry into Advanced Fluorinated Building Blocks Including all Isomeric 2‐(Trifluoromethyl)prolines

Pyrroles and their Benzo Derivatives: Applications

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