- Method for synthesis -2- of 3- methyl ester compound (methyl ethyl ester) of methyl ethyl ester (methyl) ethyl ester
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The invention relates to a synthesis method of 3-methoxy-2-aryl(methyl)acrylate compounds, which comprises the following steps: by using phenylmethyl acetate with or without substituting groups as a raw material, carrying out formylation reaction at -20-100 DEG C for 4-6 hours in a nitrogen atmosphere in the presence of Lewis acid in an aprotic solvent neutralized formylation reagent, dissociating with an organic base, hydrolyzing with hydrochloric acid, and stratifying, wherein the organic layer is an intermediate; carrying out methylation reaction on the intermediate, benzyltriethylammonium chloride, a methylation reagent and an inorganic base at 20-100 DEG C for 1-3 hours; after the reaction finishes, washing with water, desolventizing, and recrystallizing or distilling while depressurizing to obtain the product. The invention has the advantages of fewer processing steps (the methylation reaction can be directly carried out without purifying and separating the intermediate product), favorable selectivity, higher yield and low cost; and the reaction process is easy to control, and is safe and easy to amplify.
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Paragraph 0062-0065
(2019/12/25)
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- Silver-Catalyzed Olefination of Acetals and Ketals with Diazoesters to β-Alkoxyacrylates
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The first silver-catalyzed reaction of acetals or ketals with diazoesters leading to trisubstituted or tetrasubstituted β-alkoxyacrylates is now reported. A broad range of acetals and ketals bearing different substituents is compatible with this protocol and thus provides an attractive approach for the synthesis of complex β-alkoxyacrylates. The power of this method was further demonstrated by the successful synthesis of picoxystrobin, which is one of the most popular agricultural fungicides commercialized by Dupont.
- Li, Jiawen,Qian, Bo,Huang, Hanmin
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supporting information
p. 7090 - 7094
(2018/11/23)
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- Method for preparing alkoxy acrylate
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The invention discloses a method for preparing an alkoxy acrylate. The method comprises that diazo ester and substituted acetal or ketal as raw materials undergo an alkenylation reaction in the presence of Lewis acid as a catalyst at 50-120 DEG C for 1-24h, then the solvent is drained through pumping and the product is subjected to column chromatography separation so that the alkoxy acrylate compound is obtained. The reaction raw materials and the catalyst are easily available and cheap, the synthesis process is simple, the synthesis cost is greatly reduced, the reaction conditions are mild, the yield is high, the industrialization is easy, the reaction raw materials and the catalyst are clean and non-toxic, and the environmental pollution is small.
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Paragraph 0046
(2018/11/27)
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- Synthesis and evaluation of essential oil-derived β-methoxyacrylate derivatives as high potential fungicides
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Essential oils (EOs) are plant-derived aroma compounds with a wide range of biological activity, but their actions are slow, and they are typically unstable to light or heat, difficult to extract and so on. To find highly potential fungicides derived from natural EOs, a series of essential oil-based β-methoxyacrylate derivatives have been designed and synthesized. The target compounds have been screened for their potential fungicidal activity against eleven species of plant pathogen fungi, including Alternaria alternata, Phomopsis adianticola, Pestalotiopsis theae, Sclerotinia sclerotiorum, etc. Compared with intermediates I, the parent essential oils and azoxystrobin, almost all of essential oil-based β-methoxyacrylate derivatives exhibited significantly better fungicidal activity. Further investigation revealed that some compounds showed remarkable inhibitory activities against Pestalotiopsis theae, Phomopsis adianticola, Sclerotinia sclerotiorum and Magnapothe grisea at different concentrations in contrast to the commercial product azoxystrobin. Compound II-8 exhibited particularly significant fungicidal activity.
- Su, Haihuan,Wang, Wenda,Bao, Longzhu,Wang, Shuangshuang,Cao, Xiufang
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- Synthesis and antifungal potential of 1,2,3-triazole and 1,2,4-triazole thiol substituted strobilurin derivatives
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β-Methoxyacrylate group is an important pharmacophore of commercially used strobilurin fungicides. In the present study, a total of seventeen 1,2,4-triazole thiols 8a-h and 1,2,3-triazole substituted 10a-i strobilurin derivatives have been synthesized. 1,2,4-Triazole thiol substituted strobilurin derivatives 8a-h have been found to inhibit the growth of plant pathogens such as Fusarium oxysporum, Magnaporthe grisea, Drechslera oryzae and human pathogens Aspergillus fumigatus and different strains of Cryptococcus neoformans, with MIC in the range of 16-256 μg/mL. In case of Candida albicans tested strain, the MIC is > 256 μg/mL. p-Chlorophenyl substituted 1,2,4-triazole thiol strobiulrin derivative 8e is the most potent inhibitor with MIC of 16-64 μg/mL against most of the tested pathogens. Antifungal action of the compounds is due to inhibition of mitochondrial respiration. In the resazurin reduction assay, EC50 for inhibition of RZ reduction in D. oryzae by azoxystrobin and 8e are 3.42±0.03 μg/mL and 3.63±0.21 μg/mL, respectively; while in case of C. neoformans, EC50 of azoxystrobin and 8e are between 0.65-0.85 μg/mL. In a non-pathogenic model Benjaminiella poitrasii, though the MIC for all the synthesized compounds 8a-h and 10a-i are > 256 μg/ml, yeast to hypha transition is inhibited in the range of 21-75% at 4 μg/mL concentration while EC50 for inhibition of RZ reduction by azoxystrobin and 8e are 31.5±0.4 μg/mL and 17.95 ± 0.7 μg/mL, respectively. The 50% germ tube formation inhibition in case of C. albicans is observed at 108.49 μg/mL. 1,2,4-Triazole thiol substituted strobilurin derivatives hold promise for the control of pathogenic fungi in agriculture and health care.
- Chaudhary, Preeti M.,Tupe, Santosh G.,Jorwekar, Shweta U.,Sant, Duhita G.,Deshpande, Sunita R.,Maybhate, Shailaja P.,Likhite, Anjali P.,Deshpande, Mukund V.
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p. 908 - 917
(2015/08/18)
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- Synthesis and bioactivity of novel strobilurin derivatives containing the pyrrolidine-2,4-dione moiety
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(E)-Methyl-2-(2-(bromomethyl)phenyl)-3-methoxyacrylate was reacted with substituted 1-acetylpyrrolidine-2,4-diones and 3-(1-(hydroxylamino)ethylidene) pyrrolidine-2,4-diones respectively to synthesize two series of β-methoxyacrylate derivatives containing
- Lu, Gui-Hua,Chu, Hai-Bin,Chen, Min,Yang, Chun-Long
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- A METHOXYL ACRYLIC ESTER FUNGICIDE, THE PREPARATION METHOD AND USES THEREOF
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A methoxyl acrylic ester fungicide, the preparation method and uses thereof. The fungicide contains at less the following compound of formula (I) as active ingredient. The fungicide can be further prepared to form the emulsifier oil by mixing with the emulsifier, latent solvent, stabilizer, and solvent. The fungicide is useful for preventing and controlling powdery mildew, downy mildew, gray mold and tan discase of vegetable, melon and fruit, discase of vegetable, melon and fruit cased by Phoma citricarpa, leaf spot of maize, false smut, blossom-end rot of orange and Sclerotinia rot of colza et al. The fungicide has many advantages such as be effect to the strain which produced the resistance, high effect, less toxic and environmrnt-friendly.
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- Synthesis and biological activity of novel phenyltriazolinone derivatives
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Phenyltriazolinones are one of the most important classes of herbicides targeting the protoporphyrinogen oxidase enzyme. A series of triazolinone derivatives containing a strobilurin pharmacophore were designed and synthesized with the aim of discovering new phenyltriazolinone analogues with high activity. The herbicidal activity of the synthesized compounds was assayed and some of the test compounds displayed moderate herbicidal activity at 150 g ai/ha.
- Wu, Qiongyou,Wang, Guodong,Huang, Shaowei,Lin, Long,Yang, Guangfu
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p. 9024 - 9034
(2011/03/20)
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- Synthesis and fungicidal evaluation of novel chalcone-based strobilurin analogues
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Strobilurin derivatives have become one of the most important classes of agricultural fungicide due to a novel action mode, wide fungicidal spectrum, lower toxicity toward mammalian cells, and environmentally benign characteristics. To discover new strobilurin analogues with high activity against resistant pathogens, a series of new chalcone-based strobilurin derivatives are designed and synthesized by integrating a chalcone scaffold with a strobilurin pharmacophore. The preliminary bioassay showed that some of the chalcone analogues exhibited good in vivo fungicidal activities against Pseudoperoniospora cubensis and Sphaerotheca fuliginea at the dosage of 200 μg mL-1. Two compounds, (£)-methyl 2-[2-({3-[(£)-3-(2- chlorophenyl)acryloyl]phenoxy}methyl)phenyl]-3-meth-oxyacrylate (1e) and (E)-methyl 2-[2-({3-[(E)-3-(3-bromophenyl)acryloyl]phenoxy}methyl)phenyl]-3- methoxyacrylate (11), were found to display higher fungicidal activities against P. cubensis (EC90 = 118.52 μg ml-1 for 1e and EC 90 = 113.64 μg mL-1 for 11) than Kresoxim-methyl (EC90 = 154.92 μg mL-1) and were identified as the most promising candidates for further study. The present work demonstrated that strobilurin analogues containing chalcone as a side chain could be used as a lead structure for further developing novel fungicides. To our knowledge, this is the first report about the syntheses and fungicidal activities of chalcone-based strobilurin derivatives.
- Zhao, Pei-Liang,Liu, Chang-Ling,Huang, Wei,Wang, Ya-Zhou,Yang, Guang-Fu
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p. 5697 - 5700
(2008/03/14)
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