Synthesis and biological profile of 2,3-dihydro[1,3]thiazolo[4,5-b]pyridines, a novel class of acyl-ACP thioesterase inhibitors

• Jens Frackenpohl,
• David M. Barber,
• Guido Bojack,
• Birgit Bollenbach-Wahl,
• Ralf Braun,
• Rahel Getachew,
• Sabine Hohmann,
• Kwang-Yoon Ko,
• Karoline Kurowski,
• Bernd Laber,
• Rebecca L. Mattison,
• Thomas Müller,
• Anna M. Reingruber,
• Dirk Schmutzler and
• Andrea Svejda

Beilstein J. Org. Chem. 2024, 20, 540–551, doi:10.3762/bjoc.20.46

• -dihydro[1,3]thiazolo[4,5-b]pyridine; acyl-ACP thioesterase; bioisostere; herbicide; heterocycle; Introduction The presence of weed infestations exerts a high strain on food production around the globe by depleting resources for the crops and facilitating the transmission of diseases [1]. Although

• relationship (SAR) studies on selective inhibitors reduce the prevalence of undesired effects, such as toxicity in mammals [4]. Despite being employed in the field for over three decades, the mode of action of preemergence herbicide cinmethylin (1, Scheme 1) has remained unknown until 2018. At that time, the

• structural scope of modern agrochemical research and to address sustainability goals, e.g., overcoming herbicide resistance and meeting demanding environmental safety goals. Experimental Synthesis Representative procedure for the synthesis of 6-bromo-5-(2-fluorophenyl)-2,3-dihydro[1,3]thiazolo[4,5-b]pyridine

1,4-Dithianes: attractive C2-building blocks for the synthesis of complex molecular architectures

• Bram Ryckaert,
• Ellen Demeyere,
• Frederick Degroote,
• Hilde Janssens and
• Johan M. Winne

Beilstein J. Org. Chem. 2023, 19, 115–132, doi:10.3762/bjoc.19.12

• 1,4-dithianes and 1,4-dithiins (1,4-dithiin-1,1,4,4-tetraoxides), it should be noted that the dimethyl derivative 9 has actually been commercialized as the defoliating herbicide dimethipin [32]. Other 1,4-dithiin tetraoxides can be easily derived from the corresponding sulfides by treatment with an

B–N/B–H Transborylation: borane-catalysed nitrile hydroboration

• Filip Meger,
• Alexander C. W. Kwok,
• Franziska Gilch,
• Dominic R. Willcox,
• Alex J. Hendy,
• Kieran Nicholson,
• Andrew D. Bage,
• Thomas Langer,
• Thomas A. Hunt and
• Stephen P. Thomas

Beilstein J. Org. Chem. 2022, 18, 1332–1337, doi:10.3762/bjoc.18.138

• further derivatisation. 2-Chlorobenzylamine hydrochloride, a precursor to the herbicide cumyluron, was isolated in good yield (1g, 65%) [38]. Additionally, fluoro-substituted nitriles were also reduced with good efficiency (1m, 62%). Both electron-withdrawing (1n, 95%) and electron-donating (1o, 87%, 1p

Morita–Baylis–Hillman reaction of 3-formyl-9H-pyrido[3,4-b]indoles and fluorescence studies of the products

• Nisha Devi and
• Virender Singh

Beilstein J. Org. Chem. 2022, 18, 926–934, doi:10.3762/bjoc.18.92

• synthesis of various natural and synthetic products. MBH adducts itself display diverse biological activities like antifungal, antibacterial, herbicide, antiparasitic and antitumor as reviewed by Lima-Junior et al. (2012) [45]. It was envisaged that in comparison to the traditional methods like Pictet

Synthetic strategies for the preparation of γ-phostams: 1,2-azaphospholidine 2-oxides and 1,2-azaphospholine 2-oxides

• Jiaxi Xu

Beilstein J. Org. Chem. 2022, 18, 889–915, doi:10.3762/bjoc.18.90

• similar alkyl transfer from the O to N atom followed by dehydration under heating (Scheme 11) [31]. Natchev prepared racemic and optically active ethyl 2-methyl-1,2-azaphospholidine-5-carboxylate 2-oxide (69) as cyclic analogue of the herbicide phosphinothricin (glufosinate, ᴅʟ-68) from ᴅʟ-, ᴅ-, and ʟ-2

Synthesis of bis(aryloxy)fluoromethanes using a heterodihalocarbene strategy

• Carl Recsei and
• Yaniv Barda

Beilstein J. Org. Chem. 2021, 17, 813–818, doi:10.3762/bjoc.17.70

• Carl Recsei Yaniv Barda ADAMA Agan, HaAshlaag 3, Northern Industrial Zone, Ashdod, 77102, Israel 10.3762/bjoc.17.70 Abstract A side-product present in the herbicide pyroxasulfone was synthesized. The construction of a bis(aryloxy)fluoromethane moiety was necessary, for which no existing method

• was available. We report a simple, new procedure which we applied to the synthesis of some of these unusual structures. Keywords: acetal; aryloxyfluoromethane; dihalocarbene; herbicide; organofluorine; Introduction Organofluorine molecules are widely used for medicinal, agrochemical and material

• , fluoromethylene acetals. In the course of preparing synthetic samples of trace impurities in the herbicide pyroxasulfone, we were confronted with the problem of generating a bis(aryloxy)fluoromethane. Our intended route to structure 1 (Scheme 1) required the oxidation of bis-thioether 2, derived in turn from

Synthesis and herbicidal activities of aryloxyacetic acid derivatives as HPPD inhibitors

• Man-Man Wang,
• Hao Huang,
• Lei Shu,
• Jian-Min Liu,
• Jian-Qiu Zhang,
• Yi-Le Yan and
• Da-Yong Zhang

Beilstein J. Org. Chem. 2020, 16, 233–247, doi:10.3762/bjoc.16.25

• dioxygenase (HPPD) inhibitors. Preliminary bioassay results reveal that these derivatives are promising Arabidopsis thaliana HPPD (AtHPPD) inhibitors, in particular compounds I12 (Ki = 0.011 µM) and I23 (Ki = 0.012 µM), which exhibit similar activities to that of mesotrione, a commercial HPPD herbicide (Ki

• , compound II4 was safe for weed control in maize fields at a rate of 150 g ai/ha, and was identified as the most potent candidate for a novel HPPD inhibitor herbicide. The compounds described herein may provide useful guidance for the design of new HPPD inhibiting herbicides and their modification

• of HPPA to HGA is interfered with an HPPD inhibitor [9][10]; consequently, plants become severely damage when exposed to sunlight, ultimately resulting in bleaching symptoms followed by necrosis and death [11][12]. Therefore, HPPD inhibitors play important roles in the herbicide industry. In addition

A concise flow synthesis of indole-3-carboxylic ester and its derivatisation to an auxin mimic

• Marcus Baumann,
• Ian R. Baxendale and
• Fabien Deplante

Beilstein J. Org. Chem. 2017, 13, 2549–2560, doi:10.3762/bjoc.13.251

• herbicide which was required for preliminary field trials. The overall synthetic approach and optimisation studies are described along with a full description of the final reactor configurations employed for the synthesis as well as the downstream processing of the reaction streams. Keywords: flow

Nucleophilic and electrophilic cyclization of N-alkyne-substituted pyrrole derivatives: Synthesis of pyrrolopyrazinone, pyrrolotriazinone, and pyrrolooxazinone moieties

• Işıl Yenice,
• Sinan Basceken and
• Metin Balci

Beilstein J. Org. Chem. 2017, 13, 825–834, doi:10.3762/bjoc.13.83

• (Figure 1) [7][8]. Triazinone heterocycles are essential in organic synthesis regarding their herbicide, anticancer, antimicrobial, and antimetastatic activities. Metamitron (3) and metribuzin (4), 1,2,4-triazinone herbicides having an amino group, are absorbed by the roots of plants and inhibit

Cationic Pd(II)-catalyzed C–H activation/cross-coupling reactions at room temperature: synthetic and mechanistic studies

• Takashi Nishikata,
• Alexander R. Abela,
• Shenlin Huang and
• Bruce H. Lipshutz

Beilstein J. Org. Chem. 2016, 12, 1040–1064, doi:10.3762/bjoc.12.99

• temperature. In this account we disclose, in addition to full details associated with this C–H activation chemistry, additional applications of room temperature Fujiwara–Moritani reactions including a synthesis of the herbicide boscalid, as well as spectroscopic and mechanistic studies. Results and Discussion

• herbicide boscalid. Mechanistic investigations revealed that a dicationic Pd(II) complex reacts readily with an arylurea to rapidly produce a mono-cationic palladacycle at room temperature, and this likely, catalytically competent species has been characterized by X-ray crystallography. Experiments revealed

Radical-mediated dehydrative preparation of cyclic imides using (NH₄)₂S₂O₈–DMSO: application to the synthesis of vernakalant

• Dnyaneshwar N. Garad,
• Subhash D. Tanpure and
• Santosh B. Mhaske

Beilstein J. Org. Chem. 2015, 11, 1008–1016, doi:10.3762/bjoc.11.113

• such as lurasidone, phensuximide, buspirone, (R/S)-thalidomide, lenalidomide and apremilast contain cyclic imide moieties and possess a wide range of biological properties (Figure 1) [13][14][15][16][17]. Cyclic imides have found immense applications in agrochemicals such as chlorophthalim (herbicide

• ), captan (fungicide), flumipropyn (herbicide), flumioxazin (herbicide), procymidone (pesticide) and cinidon-ethyl (herbicide) [18][19]. Imides are the backbones of several commercially available high-performance polymers [20][21] and many other advanced materials [22][23][24][25]. The most commonly used

Photo, thermal and chemical degradation of riboflavin

• Muhammad Ali Sheraz,
• Sadia Hafeez Kazi,
• Sofia Ahmed,
• Zubair Anwar and
• Iqbal Ahmad

Beilstein J. Org. Chem. 2014, 10, 1999–2012, doi:10.3762/bjoc.10.208

• herbicide, 2,4-dichlorophenoxyacetic acid, in the presence of Britton–Robinson buffer at pH 6 [90]. Similarly, a catalytic effect has also been noted in acetate and carbonate buffers for RF where a change in rate of degradation was observed with an increase in pH [88]. The concentration of buffer anions has

Rh(III)-catalyzed directed C–H bond amidation of ferrocenes with isocyanates

• Satoshi Takebayashi,
• Tsubasa Shizuno,
• Takashi Otani and
• Takanori Shibata

Beilstein J. Org. Chem. 2012, 8, 1844–1848, doi:10.3762/bjoc.8.212

• structures. For instance, a 1,2-disubstituted ferrocenyl ligand, Xyliphos ((R)-1-[(S)-2-(diphenylphosphanyl)ferrocenyl]ethyl bis(3,5-dimethylphenyl)phosphane) is used for iridium-catalyzed enantioselective hydrogenation to produce the herbicide (S)-metolachlor on a scale of more than 10000 tons/year [5

Advances in synthetic approach to and antifungal activity of triazoles

• Kumari Shalini,
• Nitin Kumar,
• Sushma Drabu and
• Pramod Kumar Sharma

Beilstein J. Org. Chem. 2011, 7, 668–677, doi:10.3762/bjoc.7.79

• different substituents to the triazole nucleus. By a judicious choice of ligands, a library of new luminescent ionic iridium complexes was prepared [71]. 3-Amino-1,2,4-triazole is an inhibitor of mitochondrial and chloroplast function. Commercial grade 3-amino-1,2,4-triazole is used as a herbicide and

A new fluorescent chemosensor for fluoride anion based on a pyrrole–isoxazole derivative

• Zhipei Yang,
• Kai Zhang,
• Fangbin Gong,
• Shayu Li,
• Jun Chen,
• Jin Shi Ma,
• Lyubov N. Sobenina,
• Albina I. Mikhaleva,
• Guoqiang Yang and
• Boris A. Trofimov

Beilstein J. Org. Chem. 2011, 7, 46–52, doi:10.3762/bjoc.7.8

• compounds, and are used as antimicrobial antifungal and herbicide agents [10][11]. Research on the mechanism of anion recognition is helpful for understanding the biological activities of pyrrole–isoxazole derivatives. From UV–vis and fluorescence titration experiments it was found that the receptor 1 could