Successful fluorine-containing herbicide agrochemicals

Fujiwara, Tomoya; O’Hagan, David

doi:10.1016/j.jfluchem.2014.06.014

Cited by 766 publications

(381 citation statements)

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“…The effects of fluorination on molecular properties are well established, and their use in compound property optimisation in many fields like material 1, 2 and medicinal chemistry, [3][4][5][6] as well as crystal engineering 7,8 and agrochemistry 9,10 benefit from this strong influence. After the debate about the effective ability of fluorine to act as a hydrogen-bond (H-bond, HB) acceptor, [11][12][13][14][15] the occurrence of intermolecular OHF H-bonding is now clearly established through experimental and theoretical evidences.…”

Section: Introductionmentioning

confidence: 99%

α‐Fluoro‐o‐cresols: The Key Role of Intramolecular Hydrogen Bonding in Conformational Preference and Hydrogen‐Bond Acidity

et al. 2016

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The conformational preferences of o-cresols driven by fluorination have been thoroughly investigated from a theoretical point of view with quantum chemical methods and compared to those recently reported for benzyl alcohols. Key conformers of both families exhibit a 6-membered intramolecular hydrogen-bond (IMHB) interaction. A significant enhancement of IMHB strength is observed in -fluoro-o-cresols, owing to the simultaneous increase of the aliphatic fluorine hydrogen-bond (HB) basicity and of the aromatic hydroxyl HB acidity, compared to o-fluorobenzyl alcohols, which are characterized by aromatic fluorine atoms and aliphatic hydroxyl groups. In the case of di-and trifluorinated derivatives, the occurrence of a three-centre hydrogen-bond is emphasised and its features discussed. The impact of these structural predilections on ocresol HB properties has been characterised from the estimation of the HB acidity parameter, pKAHY, weighted according to their conformational populations. We find that -fluorination leads to an HB acidity decrease of the hydroxyl group (in contrast with o-fluorination of benzyl alcohols), whereas ,-difluorination results in no significant variation of pKAHY. Finally, an increase of HB acidity is predicted upon methyl perfluorination, which has been confirmed experimentally. Theoretical descriptors based on AIM, NCI and NBO analyses allows rationalizing the predicted trends, and reveal a relationship with the strength of the established OHF IMHB.

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Section: Introductionmentioning

confidence: 99%

α‐Fluoro‐o‐cresols: The Key Role of Intramolecular Hydrogen Bonding in Conformational Preference and Hydrogen‐Bond Acidity

et al. 2016

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“…Currently, synthesis of fluorine-containing compounds is the area of hectic research activity [1] due to the ever-increasing applications of fluorine-containing compounds in nearly every sector of chemical production, most notably, pharmaceutical [2] and agrochemical industries [3]. The scientific potential of fluoro-organic chemistry is yet to be fully explored, providing enormous motivation for the development of new chemical reactions allowing for practical access to selectively fluorinated compounds.…”

Section: Introductionmentioning

confidence: 99%

Detrifluoroacetylative cascade reactions of bicyclic fluoro-enolates with ortho -phthalaldehyde: Aspects of reactivity, diastereo- and enantioselectivity

Sha

Zhang

et al. 2017

Journal of Fluorine Chemistry

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“…Synthesis of poly substituted fluroarylazopyridone by using green protocol is of great effect in synthetic chemistry and also in pharmaceutical chemistry [12]. The presence of fluorine atoms in the molecule can change its lipophilicity, which also affect and change the rate of transportation through lipid membranes [13].…”

Section: Introductionmentioning

confidence: 99%

Green Synthesis of Novel 5-Arylazo-2- [(2S, 3S, 4R, 5R)-3, 4, 5- trihydroxy-6-(hydroxymethyl) tetrahydro-2H-pyran-2-yloxy]-4, 6-dimethyl 3-nicotinonitrile.

Mmh¹,

Ah²,

M³

et al. 2017

Chem Sci J

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Green Synthesis of Novel 5-Arylazo-2-[(2S, 3S, 4R, 5R)-3, 4, 5-trihydroxy-6-(hydroxymethyl) tetrahydro-2H-pyran-2-yloxy]-4, 6-dimethyl 3-nicotinonitrile IntroductionPyridine nucleus is one of the most interesting nucleus in organic synthesis. Many uses of pyridines derivatives were investigated in the recent decades especially fluorinated derivatives. One of the recent researches discovered that high tuberculostearic activity of pyridine was observed [1,2].Also from the amazing character of some pyridine is its high fluorescence activities which was used as molecular sensor of picric acid [3].It has been of great importance in the exploring of some novel antimicrobial compounds in veterinary as well as human medicine worldwide. Genetic mutation and acquisition of mobile drug resistance genes of microorganisms is a very great resistance and barrier in treating animal and human patients with infectious diseases [4,5]. The importance of the synthesis of novel derivatives of pyridine nucleosides due to their potential use to treat various diseases, such as hepatitis cancer and microbial infections [6][7][8][9][10].Fluorinated derivatives of pyridines are of high significance in pharmaceutical and medicinal chemistry [11]. Synthesis of poly substituted fluroarylazopyridone by using green protocol is of great effect in synthetic chemistry and also in pharmaceutical chemistry [12]. The presence of fluorine atoms in the molecule can change its lipophilicity, which also affect and change the rate of transportation through lipid membranes [13]. Achievement of green and sustainable chemistry protocol instead of classical methods synthetic chemistry nowadays is of high interest, especially in synthesis of some novel Fluro arylazo pyridine derivatives (1a-e) and their nucleosides (3a-e). Methodology ChemistryGeneral coupling procedures of synthesis of Acetylated -arylazo-2-[(2S, 3S, 4R, 5R)-3, 4, 5-trihydroxy-6-(hydroxymethyl) tetrahydro-2H-pyran-2-yloxy]-4,6dimethylnicotinonitrile AbstractPyridine derivatives played important roles in the last decade in to approach many and different functionalities, especially as antitumor, antibacterial, anti-fungal, and many of pharmacological activities. Novel compounds of 5-Arylazo-2-[(substituted)-3,4,5-trihydroxy-6-(hydroxymethyl) tetrahydro-2H-pyran-2-yloxy]-4,6dimethyl nicotine nitrile, (3a-e), generally called (Fluro arylazo pyridine glucosides) were synthesised via green protocol, microwave scheme 3, and the compounds were investigated on the basis of spectroscopic data (FT-IR, 1D, 13 C), and antibacterial and antifungal studies had been applied. Microwave method: A mixture of 2(1H)-pyridines (1a-e) (10 mmol) and 1″,2″,3″,4″,6″-penta-O-acetyl-α-D-glucopyranose (11 mmol, 4.29 g) where be dissolved in a mixture of methylene chloride/methanol (80/20) then silica gel (200-400 mesh) where be added after that the excess solvent was removed by evaporation. The dried residue was transferred into a 10 mL vial and subjected to microwave irradiation for 2-3 minutes using CEM Microwave syst...

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Successful fluorine-containing herbicide agrochemicals

Cited by 766 publications

References 58 publications

α‐Fluoro‐o‐cresols: The Key Role of Intramolecular Hydrogen Bonding in Conformational Preference and Hydrogen‐Bond Acidity

α‐Fluoro‐o‐cresols: The Key Role of Intramolecular Hydrogen Bonding in Conformational Preference and Hydrogen‐Bond Acidity

Detrifluoroacetylative cascade reactions of bicyclic fluoro-enolates with ortho -phthalaldehyde: Aspects of reactivity, diastereo- and enantioselectivity

Green Synthesis of Novel 5-Arylazo-2- [(2S, 3S, 4R, 5R)-3, 4, 5- trihydroxy-6-(hydroxymethyl) tetrahydro-2H-pyran-2-yloxy]-4, 6-dimethyl 3-nicotinonitrile.

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