Isolation, Synthesis, and Fungicidal Activity of Isopropyl (3-methyl-1-oxo-1-((1-((4-(prop-2-yn-1-yloxy)phenyl)thio)propan-2-yl)amino)butan-2-yl)carbamate Diastereomers against Phytophthora capsici

IF 1.1 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Heteroatom Chemistry Pub Date : 2022-08-05 DOI:10.1155/2022/4678338

Lei Tian, Yang Gao, Xing-Jie Peng, Cheng Zhang, Wei-Guang Zhao, Xing-Hai Liu

引用次数: 0

Abstract

Two isopropyl (3-methyl-1-oxo-1-((1-((4-(prop-2-yn-1-yloxy)phenyl)thio)propan-2-yl)amino)butan-2-yl)carbamate diastereomers were isolated. Fungicidal activities indicated that the isolated four chiral compounds possessed excellent activity against P. capsici with the EC50 value of 4a (1.30 μg/mL), 4b (0.078 μg/mL), 4c (1.85 μg/mL), and 4d (44.4 μg/mL). Among them, compound 4b exhibited remarkably high activities against Phytophthora capsici, which is better than that of positive control dimethomorph. Its R and S isomers showed that chiral influences the activity against P. capsici.

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3-甲基-1-氧代-1-（（1-（（4-（丙-2-炔-1-基氧基）苯基）硫基）丙-2-基）氨基）丁-2-基氨基甲酸异丙酯双立体异构体的分离、合成及其对辣椒疫霉的杀菌活性

分离出两个异丙基（3-甲基-1-氧代-1-（（1-（（4-（丙-2-炔-1-基氧基）苯基）硫基）丙-2-基）氨基）丁-2-基）氨基甲酸酯非对映体。结果表明，分离得到的4个手性化合物对辣椒假单胞菌具有良好的杀菌活性，其EC50值为4a（1.30 μg/mL），4b（0.078 μg/mL），4c（1.85 μg/mL）和4d（44.4 μg/mL）。其中，化合物4b对辣椒疫霉菌的活性显著高于阳性对照的二甲吗啉。其R和S异构体显示手性影响对辣椒假单胞菌的活性。

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来源期刊

Heteroatom Chemistry 化学-化学综合

CiteScore

1.20

自引率

0.00%

发文量

审稿时长

6 months

期刊介绍： Heteroatom Chemistry brings together a broad, interdisciplinary group of chemists who work with compounds containing main-group elements of groups 13 through 17 of the Periodic Table, and certain other related elements. The fundamental reactivity under investigation should, in all cases, be concentrated about the heteroatoms. It does not matter whether the compounds being studied are acyclic or cyclic; saturated or unsaturated; monomeric, polymeric or solid state in nature; inorganic, organic, or naturally occurring, so long as the heteroatom is playing an essential role. Computational, experimental, and combined studies are equally welcome. Subject areas include (but are by no means limited to): -Reactivity about heteroatoms for accessing new products or synthetic pathways -Unusual valency main-group element compounds and their properties -Highly strained (e.g. bridged) main-group element compounds and their properties -Photochemical or thermal cleavage of heteroatom bonds and the resulting reactivity -Uncommon and structurally interesting heteroatom-containing species (including those containing multiple bonds and catenation) -Stereochemistry of compounds due to the presence of heteroatoms -Neighboring group effects of heteroatoms on the properties of compounds -Main-group element compounds as analogues of transition metal compounds -Variations and new results from established and named reactions (including Wittig, Kabachnik–Fields, Pudovik, Arbuzov, Hirao, and Mitsunobu) -Catalysis and green syntheses enabled by heteroatoms and their chemistry -Applications of compounds where the heteroatom plays a critical role. In addition to original research articles on heteroatom chemistry, the journal welcomes focused review articles that examine the state of the art, identify emerging trends, and suggest future directions for developing fields.