- Design and synthesis of florylpicoxamid, a fungicide derived from renewable raw materials
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The design and synthesis of the broad-spectrum fungicide, florylpicoxamid, embodies multiple Green Chemistry principles. The active ingredient was strategically designed to deliver maximum biological activity and rapidly degrade after application to minimize its enviromental impact. Unlike many chiral crop protection chemicals, florylpicoxamid was purposely developed as a single stereoisomer to minimize the dose rate of this product in field applications and avoid any potential environmental burdens of its less active stereoisomers. Fortunately, the most efficacious stereoisomer of the natural product-inspired active ingredient can be derived from the natural antipodes of lactic acid and alanine. The principles of Green Chemistry were also used to improve the synthetic route originally developed for structure-activity relationship studies, resulting in a convergent stereoselective synthesis that is more sustainable and cost-effective. The streamlined 2ndgeneration route decreases the use of protecting groups and utilizes safer reaction solvents. Development of a novel synthetic sequence to the 2,3,4-trisubstituted pyridine motif from furfural further increased the renewable carbon content of the active ingredient to nearly 50%. Throughout process development, improved reaction conditions and industrially-preferred alternatives were identified to replace hazardous reagents for key transformations. In all, the holistic use of Green Chemistry principles in the design and synthesis of florylpicoxamid will provide farmers with a highly sustainable product for crop disease management.
- Babij, Nicholas R.,Choy, Nakyen,Cismesia, Megan A.,Couling, David J.,Hough, Nicole M.,Johnson, Peter L.,Klosin, Jerzy,Li, Xiaoyong,Lu, Yu,McCusker, Elizabeth O.,Meyer, Kevin G.,Renga, James M.,Rogers, Richard B.,Stockman, Kenneth E.,Webb, Nicola J.,Whiteker, Gregory T.,Zhu, Yuanming
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p. 6047 - 6054
(2020/10/18)
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- PROCESS FOR THE PREPARATION OF 4-ALKOXY-3-ACETOXYPICOLINIC ACIDS
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4-Alkoxy-3-hydroxypicolinic acids may be conveniently prepared from 4,6-dibromo-3-hydroxypicolinonitrile in a series of chemical steps selected from bromo substitution, nitrile hydrolysis and halogen reduction that are conducted as a single pot process. 4,6-Dibromo-3-hydroxypicolinonitrile may be prepared from furfural in a series of chemical steps selected from cyano-amination, amine salt formation and bromination-rearrangement. 4-Alkoxy-3-acetoxypicolinic acids may be conveniently prepared from 4-alkoxy-3-hydroxypicolinic acids by treatment with acetic anhydride.
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- PROCESS FOR THE PREPARATION OF 4-ALKOXY-3-HYDROXYPICOLINIC ACIDS
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4-Alkoxy-3-hydroxypicolinic acids may be conveniently prepared from 4,6-dibromo-3-hydroxypicolinonitrile in a series of chemical steps selected from bromo substitution, nitrile hydrolysis and halogen reduction that are conducted as a single pot process. 4,6-Dibromo-3-hydroxypicolinonitrile may be prepared from furfural in a series of chemical steps selected from cyano-amination, amine salt formation and bromination-rearrangement.
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- PROCESS FOR THE PREPARATION OF 4-ALKOXY-3-ACETOXYPICOLINIC ACIDS
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4-Alkoxy-3-hydroxypicolinic acids may be conveniently prepared from 4,6-dibromo-3-hydroxypicolinonitrile in a series of chemical steps selected from bromo substitution, nitrile hydrolysis and halogen reduction that are conducted as a single pot process. 4,6-Dibromo-3-hydroxypicolinonitrile may be prepared from furfural in a series of chemical steps selected from cyano-amination, amine salt formation and bromination-rearrangement. 4-Alkoxy-3-acetoxypicolinic acids may be conveniently prepared from 4-alkoxy-3-hydroxypicolinic acids by treatment with acetic anhydride.
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- PROCESS FOR THE PREPARATION OF 4-ALKOXY-3-HYDROXYPICOLINIC ACIDS
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4,6-Dibromo-3-hydroxypicolinonitrile may be prepared from furfural in a series of chemical steps selected from cyano-amination, amine salt formation and bromination-rearrangement. 4-Alkoxy-3-hydroxypicolinic acids may be conveniently prepared from 4,6-dibromo-3-hydroxypicolinonitrile in a series of chemical steps selected from bromo substitution, nitrile hydrolysis and halogen reduction.
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Paragraph 0082; 0083
(2016/02/10)
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- PICOLINAMIDE DERIVATIVES AND PEST CONTROLLERS CONTAINING THE SAME AS THE ACTIVE INGREDIENT
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Disclosed are novel compounds useful for the control of harmful organisms, harmful organism control agents using the same, and processes for producing the novel compounds. The useful novel compounds according to the present invention include compounds represented by formula (1). The compounds represented by formula (1) have potent activity against harmful organisms, and do not have phytotoxicity against agricultural and gardening plants, as objects to which the compounds of the present invention are applied for preventive and exterminating purposes, and human beings and beasts. wherein A represents a bond or an optionally substituted alkylene chain; R1 represents one or more groups, which may be the same or different, selected from the group consisting of a hydrogen atom, alkoxy, and haloalkoxy; R2 represents a hydrogen atom, benzyl, alkyl or alkanoyl, in which the groups other than the hydrogen atom may be substituted; and R3 represents a hydrogen atom, cycloalkyl, cycloalkenyl, aryl or a heterocyclic group, in which the groups other than the hydrogen atom may be substituted, excluding the case where R1 represents a hydrogen atom, A represents a bond or a methylene chain, and R3 represent phenyl or cyclohexyl, and the case where A represents an alkylene chain and R3 represents a hydrogen atom.
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- Enantioselective total synthesis of the antifungal dilactone, UK-2A: The determination of the relative and absolute configurations
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The synthesis of the antifungal dilactone, UK-2A, is described. In addition to providing a workable synthetic route to this potent antifungal antibiotic, this has allowed us to determine the assignment of the relative and absolute configurations in the nine-membered ring.
- Shimano, Masanao,Shibata, Tetsuo,Kamei, Noriyuki
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p. 4363 - 4366
(2007/10/03)
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- Total synthesis of the antifungal dilactones UK-2A and UK-3A: The determination of their relative and absolute configurations, analog synthesis and antifungal activities
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The synthesis of the antifungal dilactones, UK-2A and UK-3A, is described. In addition to providing a workable synthetic route to these potent antifungal antibiotics, this has allowed us to determine the assignment of the relative and absolute configurations in the nine-membered ring. Furthermore, UK-2A analogs were also synthesized and evaluated their antifungal activities and cytotoxic activities along with UK-2A, (2R, 3R, 4S, 7R)-UK-2A, UK-3A, (2R, 3R, 4S, 7R)-UK-3A, and antimycin A. The structural requirements for the selective cytotoxicity against yeasts and filamentous fungi will also be suggested.
- Shimano, Masanao,Kamei, Noriyuki,Shibata, Tetsuo,Inoguchi, Kiyoshi,Itoh, Nobuko,Ikari, Takashi,Senda, Hisato
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p. 12745 - 12774
(2007/10/03)
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