- Synthesis and bio-evaluation of natural butenolides-acrylate conjugates
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A series of novel 3-aryl-4-hydroxy-2(5H) furanone-acrylate hybrids were designed and synthesized based on the natural butenolides and acrylates scaffolds. The structures of the prepared compounds were characterized by 1H-NMR, 13C-NMR and electrospray ionization mass spectrometry (ESI-MS), and the bioactivity of the target compounds against twelve phytopathogenic fungi was investigated. The preliminary in vitro antifungal activity screening showed that most of the target compounds had moderate inhibition on various pathogenic fungi at the concentration of 100 mg·L?1, and presented broad-spectrum antifungal activities. Further studies also indicated that compounds 7e and 7k still showed some inhibitory activity against Pestallozzia theae, Sclerotinia sclerotiorum and Gibberella zeae on rape plants at lower concentrations, which could be optimized as a secondary lead for further research.
- Bao, Longzhu,Wang, Shuangshuang,Song, Di,Wang, Jingjing,Cao, Xiufang,Ke, Shaoyong
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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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- 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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- METHOXYACRYLATE-BASED FUNGICIDE AND METHODS FOR PREPARING AND USING THE SAME
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A pharmaceutical composition of fungicide including at least a compound represented by Formula (I). The pharmaceutical composition of fungicide can further include an emulsifier, a cosolvent, a stabilizer, and a solvent. The fungicide can prevent and treat powdery mildew, downy mildew, gray mold, brown spot, scab of vegetables and fruits, southern leaf blight of corn, rice false smut, citrus stem-end rot, and rape sclerotinia rot, with high efficiency, low toxicity, and relative environmental friendliness. A method of preparing the fungicide and a method of using thereof are also provided.
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Page/Page column 3
(2010/12/18)
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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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- Fungicidal compounds having a fluorovinyl-or fluoropropenyl-oxyphenyloxime moiety and process for the preparation thereof
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A fungicidal compound of formula (I) having a fluorovinye- or fluoropropenyl-oxyphenyloxime moiety and stereoisomers thereof are useful for protecting crops from fungal diseases: wherein, X is CH or N; Y is O or NH; R1is hydrogen, C1-4alkyl, or halogen-substituted C1-4alkyl, R2is a phenyl group optionally carrying one or more substituents selected from the group consisting of C1-4alkyl, C1-4alkoxy, methylenedioxy and halogen; or a naphthyl group; and R3is hydrogen or CF3.
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- Fungicidial compounds having a fluorovinyloxphyenyl moiety and process for the preparation thereof
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A fungicidal compound of formula (I) having a fluorovinyloxyphenyl moiety and stereoisomers thereof are useful for protecting crops from fungal diseases: wherein: X is CH or N; Y is O or S; Z is O or NH; R1is hydrogen or CF3; and R2is hydrogen, a C1-10alkyl, naphthyl, thiophenyl or a phenyl group optionally carrying one or more substituents selected from the group consisting of C1-6alkyl, halogen-substituted C1-6alkyl, C1-6alkoxy, phenoxy, halogen, and methylenedioxy radicals.
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- Process for preparation of thiazolylalkoxy acrylates
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A process for the preparation of a compound of the formula STR1 wherein R1 and R2 are individually selected from the group consisting of hydrogen, halogen, --CF3, alkyl, alkoxy and alkylthio of 1 to 8 carbon atoms, alkenyl and alkynyl of 2 to 8 carbon atoms, --SO2 alk and alk is alkyl of 1 to 8 carbon atoms, optionally substituted aryl, aryloxy and arylthio of 6 to 18 carbon atoms and optionally substituted heteroaryl, heteroaryloxy and heterocyclic of 5 to 6 ring members, R3 is selected from the group consisting of alkyl of 1 to 8 carbon atoms, alkenyl and alkynyl of 2 to 8 carbon atoms, aryl of 6 to 18 carbon atoms and alkoxyalkoxyalkyl of 3 to 14 carbon atoms, X is selected from the group consisting of --O--, --S-- and --NR4 --, R4 is selected from the group consisting of hydrogen, alkyl, alkenyl and alkynyl of up to 8 carbon atoms, --SO2 alkyl, --SO2 alkenyl and --SO2 alkynyl of up to 8 carbon atoms and optionally substituted aryl and --SO2 aryl of 6 to 18 carbon atoms, the double bond between the heterocycle of 5 member ring and the aromatic nucleus is of E and/or Z geometry comprising reacting a halide of the formula STR2 wherein R3 is as defined above and Hal is hydrogen with a compound of the formula STR3 wherein X, R1 and R2 have the above definitions in the presence of a base to obtain the corresponding product of formula I in the form of a mixture of isomers and optionally separating the isomers and novel intermediates of formula II.
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