Syntheses and herbicidal activity of pyrazolyl benzoxazole derivatives

Xue, Na; Zhou, Yuhan; Wang, Guowei; Miao, Weirong; Qü, Jingping

doi:10.1002/jhet.134

Cited by 17 publications

(9 citation statements)

References 15 publications

(10 reference statements)

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“…Pyrazole derivatives have great importance in the medicinal and pesticide fields [13,14,15], due to their broad range of biological activity [16,17,18]. The molecules of many modern drugs with antiphlogistic, antidiabetic, analgesic, and acaricidal activity in medicine [19] and herbicidal [20,21,22], antibacterial [23,24,25], acaricidal and insecticide [26,27] in the pesticide area contain pyrazole rings as a structural fragment.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis and Anti-Tobacco Mosaic Virus (TMV) Activity of 5-Chloro-N-(4-cyano-1-aryl-1H-pyrazol-5-yl)-1-aryl-3-methyl-1H-pyrazole-4-carboxamide Derivatives

et al. 2015

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A series of novel pyrazole amide derivatives 3a-3p which take TMV PC protein as the target has been designed and synthesized by the reactions of 5-chloro-1-aryl-3-methyl-1H-pyrazole-4-carboxylic acids with 5-amino-1-aryl-1H-pyrazole-4-carbonitriles. All the compounds were characterized by 1 H-NMR, mass spectroscopy and elemental analysis. Preliminary bioassays indicated that all the compounds acted against the tobacco mosaic virus (TMV) with different in vivo and in vitro modes at 500 μg/mL and were found to possess promising activity. Especially, compound 3p showed the most potent biological activity against tobacco mosaic virus (TMV) compared to ningnanmycin, and a molecular docking study was performed and the binding model revealed that the pyrazole amide moiety was tightly embedded in the binding sites of TMV PC (PDB code: 2OM3).

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Section: Introductionmentioning

confidence: 99%

Design, Synthesis and Anti-Tobacco Mosaic Virus (TMV) Activity of 5-Chloro-N-(4-cyano-1-aryl-1H-pyrazol-5-yl)-1-aryl-3-methyl-1H-pyrazole-4-carboxamide Derivatives

et al. 2015

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“…Benzoxazinederivatives have attracted widespread attention due to theirbroad applicationsinagriculture [1][2][3]. Moreover, benzoxazines were useful compounds as starting materials for the synthesis of larger structures with valuable biological activities [4][5][6].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of N-dichloroacetyl-3-methyl-6,8-dichloro-3,4-dihydro- 2H-1,4-benzoxazine, C11H9Cl4NO2

Cheng

2014

Zeitschrift Für Kristallographie - New Crystal Structures

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C 11 H 9 Cl 4 NO 2 ,monoclinic, P2 1 /c (no.14), a =11.995(2) Å, b =11.831(2)Å,c=9.798(2) Å, b =108.65(3)°, V =1317.5Å 3 ,Z=4,R gt (F) =0.0374, wR ref (F 2 ) =0.1050, T =293 K. Source of materialDichloroacetyl chloride (17.6m mol) wasa dded slowly in the mixture containing 3-methyl-6,8-dichloro-3,4-dihydro-2H-1,4-benzoxazine (14 mmol), Na 2 CO 3 (15.2 mmol), and benzene (25 mL). Thesystem was stirred at room temperature for 2h and TLC monitored. Then the mixture was rinsed, and the organic phase was dried over anhydrous magnesium sulfate. Benzene was removed under vacuum.The crude product was collected as white solid in 48% yield, and recrystallized from ethanol and light petroleum. Experimental detailsThe C-H atomswere then constrained to an ideal geometry, with C-H distances of 0.93-0.98 Å. The U iso values of the hydrogen atomsofmethyl groups were set to 1.5U eq (C methyl )and the U iso values of all other hydrogen atomswere set to 1.2U eq (C). DiscussionBenzoxazinederivatives have attracted widespread attention due to theirbroad applicationsinagriculture[1-3]. Moreover, benzoxazines were useful compounds as starting materials for the synthesis of larger structures with valuable biological activities [4][5][6]. N-Dichloroacetylb enzoxazines were used as herbicide safeners [7,8]. This contribution is acontinuation of our work to prepare and characterize N-dichloroacetyl-3-methyl-3,4-dihydro-1,4-benzoxazine through O-alkylation, reduction, cyclization and acylation reactions [9]. Thetitle molecule is composedoftwo planarrings,and it is obviousthatbenzene planeand oxazineringplane were almost in the sameplane with dihedral angle of 9.32(6)°. The torsion angles of N1-C7-C8-N2 was 60.3(2)°, showing ahalf-chair conformation. Obviously there is a large conjunctive effect between O1, benzene ring, N1, C9-O2 [C=O], which resulted in the shorter bond length than the typical C-N bond length and C-O bond length. In the crystal, molecules ares tablized by weak C-H×××Oh ydrogen bonds and van der Waals forces.

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“…All of the hydrogen atoms were generated and refined in ideal positions. Crystallographic parameters of 5b: empirical formula: C 17 …”

Section: Preparation Of 4a-cmentioning

confidence: 99%

Synthesis, Structure and Herbicidal Activity of Substituted Phenyl Pyrazole Derivatives

Zhou

Xue

Wang

et al. 2010

Journal of Chemical Research

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To search for novel Protox inhibitors, a series of phenyl and 1,4-benzoxazin-5-yl pyrazole derivatives were synthesised from 3-(4-chloro-2-fluoro-5-methoxyphenyl)-1-methyl-5-trifluoromethyl-1H-pyrazole or its halogen substituted derivatives, via a serial of reactions that included nitration, reduction, acetylation, ring closure, methylation, etc. The single crystal of 2-(N-acetylacetamido)-6-chloro-3-[4-chloro-5-(trifluoromethyl)-1-methyl-1H-pyrazol-3-yl]-4-fluorophenyl acetate was prepared, and its structure was determined by X-ray analysis. The preliminary bioassay test shows that some of the compounds have high bioactivity. Especially, even at a low dosage of 150 g hm −2 , 2-(N-acetylacetamido)-6-chloro-3-[4-chloro-5-(trifluoromethyl)-1-methyl-1H-pyrazol-3-yl]-4-fluorophenyl acetate exhibited high activity, the inhibiting rate for both of the weeds reached above 90%.

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Syntheses and herbicidal activity of pyrazolyl benzoxazole derivatives

Cited by 17 publications

References 15 publications

Design, Synthesis and Anti-Tobacco Mosaic Virus (TMV) Activity of 5-Chloro-N-(4-cyano-1-aryl-1H-pyrazol-5-yl)-1-aryl-3-methyl-1H-pyrazole-4-carboxamide Derivatives

Design, Synthesis and Anti-Tobacco Mosaic Virus (TMV) Activity of 5-Chloro-N-(4-cyano-1-aryl-1H-pyrazol-5-yl)-1-aryl-3-methyl-1H-pyrazole-4-carboxamide Derivatives

Crystal structure of N-dichloroacetyl-3-methyl-6,8-dichloro-3,4-dihydro- 2H-1,4-benzoxazine, C11H9Cl4NO2

Synthesis, Structure and Herbicidal Activity of Substituted Phenyl Pyrazole Derivatives

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