Synthesis and herbicidal activity of 4, 8-DHT and its derivates

Zhang, Jianhong; Yang, Li; Ruan, Xiuxiu; Sheng, Zheng; Yu, Min-fen; Zheng, Bingsong; Zhang, Jin-yun; Li, Xianxian; Zhao, Yongjie; Wang, Qiang

doi:10.1016/j.indcrop.2017.11.051

Cited by 6 publications

(8 citation statements)

References 35 publications

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“…Infrared (IR) spectra were recorded on a PerkinElmer 8900 at the Department of Chemistry, Faculty of Science, KMITL. 1 H and 13 C NMR spectra were recorded on a Bruker AVANCE III HD (500 MHz) at The Equipment Center, Chulalongkorn University, using residual protonated chloroform (CDCl 3 , 7.27 ppm for 1 H NMR and 77.00 ppm for 13 C NMR), residual protonated methanol (CD 3 OD, 3.31 ppm for 1 H NMR and 49.00 ppm for 13 C NMR), or residual protonated dimethyl sulfoxide (DMSO-d 6 , 2.50 ppm for 1 H NMR and 39.52 ppm for 13 C NMR) as internal standard. High-resolution mass spectra were recorded on a Bruker micrOTOF II mass spectrometer at the Faculty of Science, Ramkhamhaeng University, and a Bruker Daltonics (micrO-TOF) at the Faculty of Science, Mahidol University.…”

Section: ■ Conclusionmentioning

confidence: 99%

“…Percent yields, melting points, retardation factor (R f ), IR spectra, 1 H NMR spectra, 13 C NMR spectra, and highresolution mass spectra of new compounds (PDF)…”

Section: * S Supporting Informationmentioning

confidence: 99%

“…Generally, there are numerous methods of weeding, such as biological, chemical, manual, and mechanical. − Among these, herbicides are still widespread . Moreover, since the discovery of the concept of allelopathy , agrochemists have been investigating the effect of allelochemicals on weeds and crop plants to produce natural product herbicides. − Further, to discover new and effective weed killers, chemists have also formed derivatives of allelochemicals − to find selective and eco-friendly herbicides.…”

Section: Introductionmentioning

confidence: 99%

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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: ■ Conclusionmentioning

confidence: 99%

“…Percent yields, melting points, retardation factor (R f ), IR spectra, 1 H NMR spectra, 13 C NMR spectra, and highresolution mass spectra of new compounds (PDF)…”

Section: * S Supporting Informationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

2019

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“…Therefore, the development for sustainable herbicides with high activity and low toxicity has attracted a lot of interest. − Relative to synthetic herbicides, most botanical herbicides extracted or derived from plants have received much more attention due to their lower toxicity and lower risk to mammals and ecological environments, respectively. − …”

Section: Introductionmentioning

confidence: 99%

Turpentine Derived Secondary Amines for Sustainable Crop Protection: Synthesis, Activity Evaluation and QSAR Study

XiaoJing

Dai

et al. 2020

J. Agric. Food Chem.

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In this study, we will report on the synthesis and application of efficient botanical agrochemicals from turpentine for sustainable crop protection. Two series of turpentine derived secondary amines were synthesized and identified by FT-IR, 1H NMR, 13C NMR, and HRMS. The herbicidal activities against Echinochloa crus-galli were evaluated. The potential toxicity of the synthesized compounds was tested by MTT cytotoxicity analysis. The effect of structure of the synthesized secondary amines and corresponding Schiff base compounds on their activities was investigated by quantitative structure–activity relationship (QSAR) study. All target products were found to be low toxicity, with similar or higher herbicidal activities than commercial herbicides diuron and Glyphosate. Results of QSAR study showed that a best four-descriptor QSAR model with R 2 of 0.880 and R loo 2 of 0.818 was obtained. The four descriptors most relevant to the herbicidal activities are the min valency of a N atom, the max total interaction for a C−H bond, the relative number of aromatic bonds, and the min partial charge (Q min ).

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“…1,5-Dihydroxynaphthalene (C 10 H 8 O 2 , 1,5-DHN, CAS No. 83-56-7), an important intermediate product in chemical industry, can be applied in organic synthesis, , dyestuffs, , medicine, , the photographic industry, and other fields. , With the development of it is downstream products in recent years, 1,5-DHN has a better market in China. , …”

Section: Introductionmentioning

confidence: 99%

Optimal Design of Neutralization Process in 1,5-Dihydroxynaphthalene Production with Solubility Difference of Naphthalene-1,5-disulfonic Acid and Naphthalene-1,5-disulfonic Acid Disodium in Aqueous Sulfuric Acid Solutions

Zhao

Pei

et al. 2018

Ind. Eng. Chem. Res.

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An optimal design of the neutralization process in 1,5-dihydroxynaphthalene production was proposed and discussed. In the new strategy, instead of sodium chloride, sodium sulfate was used in the salting-out process to overcome the drawbacks of the traditional strategy. Then the precipitated mixtures, mainly naphthalene-1,5-disulfonic acid (1,5-H 2 NDS) and sodium sulfate, were neutralized to obtain naphthalene-1,5-disulfonic acid disodium (1,5-Na 2 NDS) and sulfuric acid. By adjusting the concentrations of sulfuric acid solutions to 0.3 and 0.5 mass fractions, 1,5-Na 2 NDS and 1,5-H 2 NDS were precipitated out, respectively. The yields of both 1,5-H 2 NDS and 1,5-Na 2 NDS reached 0.98. 1,5-Na 2 NDS was sent to the alkali fusion process, while 1,5-H 2 NDS was reused in the neutralization. In neutralization, the mole ratio (1,5-H 2 NDS to sodium sulfate) was chosen as 2.5 and the reaction temperature was 353 K. In order to determine the separation conditions, the solubilities of 1,5-H 2 NDS•2H 2 O and 1,5-Na 2 NDS•H 2 O in aqueous sulfuric acid solutions were measured over the temperature range from 277 to 337 K at atmospheric pressure by a dynamic method. The new strategy is particularly instructive for the industrial production of 1,5dihydroxynaphthalene.

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Synthesis and herbicidal activity of 4, 8-DHT and its derivates

Cited by 6 publications

References 35 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.

Turpentine Derived Secondary Amines for Sustainable Crop Protection: Synthesis, Activity Evaluation and QSAR Study

Optimal Design of Neutralization Process in 1,5-Dihydroxynaphthalene Production with Solubility Difference of Naphthalene-1,5-disulfonic Acid and Naphthalene-1,5-disulfonic Acid Disodium in Aqueous Sulfuric Acid Solutions

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