Synthesis and antifungal activity of β mrifluoroalkyl aminovinyl ketone derivatives

Gary Gellerman; Natali Pariente; Paz Zahi; Anat Shnaiderman; Oded Yarden

doi:10.1021/jf902190w

Synthesis and antifungal activity of β mrifluoroalkyl aminovinyl ketone derivatives

Gary Gellerman, Natali Pariente, Paz Zahi, Anat Shnaiderman, Oded Yarden^*

^*Corresponding author for this work

Department of Plant Pathology and Microbiology

Research output: Contribution to journal › Article › peer-review

10 Scopus citations

Abstract

Ten β-trifluoroalkyl aminovinyl ketone derivatives were synthesized, and their inhibitory effects on several phytopathogenic fungi, an oomycete and plants were assessed. The various compounds were fungitoxic at the 10-100 μM range, with (Z)-3-amino-4,4,4-trifluoro-1-(4-chlorophenyl)but-2-en1-one exhibiting the highest inhibitory effect on most of the test pathogens. Alternarla alternata and Neurospora crassa were the most tolerant and sensitive fungi to the compounds, respectively. We propose that (Z)-3-amino-4,4,4- trifluoro-1-phenylbut-2-en-1-one is the minimal structural requirement for a β-trifluoroalkyl aminovinyl ketone fungitoxic derivative.

Original language	English
Pages (from-to)	8303-8307
Number of pages	5
Journal	Journal of Agricultural and Food Chemistry
Volume	57
Issue number	18
DOIs	https://doi.org/10.1021/jf902190w
State	Published - 23 Sep 2009

Keywords

Alternarla alternata
Antifungal
Botrytis cinerea
Neurospora crassa
Penicillium dlgltatum
Pythlum aphanldermatum
Rhizoctonia sollanl
Sclerotinia sclerotiorum
Structure-activity relationship
β-trlfluoroalkyl aminovinyl ketone derivatives

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10.1021/jf902190w

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title = "Synthesis and antifungal activity of β mrifluoroalkyl aminovinyl ketone derivatives",

abstract = "Ten β-trifluoroalkyl aminovinyl ketone derivatives were synthesized, and their inhibitory effects on several phytopathogenic fungi, an oomycete and plants were assessed. The various compounds were fungitoxic at the 10-100 μM range, with (Z)-3-amino-4,4,4-trifluoro-1-(4-chlorophenyl)but-2-en1-one exhibiting the highest inhibitory effect on most of the test pathogens. Alternarla alternata and Neurospora crassa were the most tolerant and sensitive fungi to the compounds, respectively. We propose that (Z)-3-amino-4,4,4- trifluoro-1-phenylbut-2-en-1-one is the minimal structural requirement for a β-trifluoroalkyl aminovinyl ketone fungitoxic derivative.",

keywords = "Alternarla alternata, Antifungal, Botrytis cinerea, Neurospora crassa, Penicillium dlgltatum, Pythlum aphanldermatum, Rhizoctonia sollanl, Sclerotinia sclerotiorum, Structure-activity relationship, β-trlfluoroalkyl aminovinyl ketone derivatives",

author = "Gary Gellerman and Natali Pariente and Paz Zahi and Anat Shnaiderman and Oded Yarden",

year = "2009",

month = sep,

day = "23",

doi = "10.1021/jf902190w",

language = "אנגלית",

volume = "57",

pages = "8303--8307",

journal = "Journal of Agricultural and Food Chemistry",

issn = "0021-8561",

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T1 - Synthesis and antifungal activity of β mrifluoroalkyl aminovinyl ketone derivatives

AU - Gellerman, Gary

AU - Pariente, Natali

AU - Zahi, Paz

AU - Shnaiderman, Anat

AU - Yarden, Oded

PY - 2009/9/23

Y1 - 2009/9/23

N2 - Ten β-trifluoroalkyl aminovinyl ketone derivatives were synthesized, and their inhibitory effects on several phytopathogenic fungi, an oomycete and plants were assessed. The various compounds were fungitoxic at the 10-100 μM range, with (Z)-3-amino-4,4,4-trifluoro-1-(4-chlorophenyl)but-2-en1-one exhibiting the highest inhibitory effect on most of the test pathogens. Alternarla alternata and Neurospora crassa were the most tolerant and sensitive fungi to the compounds, respectively. We propose that (Z)-3-amino-4,4,4- trifluoro-1-phenylbut-2-en-1-one is the minimal structural requirement for a β-trifluoroalkyl aminovinyl ketone fungitoxic derivative.

AB - Ten β-trifluoroalkyl aminovinyl ketone derivatives were synthesized, and their inhibitory effects on several phytopathogenic fungi, an oomycete and plants were assessed. The various compounds were fungitoxic at the 10-100 μM range, with (Z)-3-amino-4,4,4-trifluoro-1-(4-chlorophenyl)but-2-en1-one exhibiting the highest inhibitory effect on most of the test pathogens. Alternarla alternata and Neurospora crassa were the most tolerant and sensitive fungi to the compounds, respectively. We propose that (Z)-3-amino-4,4,4- trifluoro-1-phenylbut-2-en-1-one is the minimal structural requirement for a β-trifluoroalkyl aminovinyl ketone fungitoxic derivative.

KW - Alternarla alternata

KW - Antifungal

KW - Botrytis cinerea

KW - Neurospora crassa

KW - Penicillium dlgltatum

KW - Pythlum aphanldermatum

KW - Rhizoctonia sollanl

KW - Sclerotinia sclerotiorum

KW - Structure-activity relationship

KW - β-trlfluoroalkyl aminovinyl ketone derivatives

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SN - 0021-8561

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SP - 8303

EP - 8307

JO - Journal of Agricultural and Food Chemistry

JF - Journal of Agricultural and Food Chemistry

IS - 18

ER -

Synthesis and antifungal activity of β mrifluoroalkyl aminovinyl ketone derivatives

Abstract

Keywords

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