Synthesis and antifungal activity of beta-trifluoroalkyl aminovinyl ketone derivatives.
Ten beta-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 microM range, with (Z)-3-amino-4,4,4-trifluoro-1-(4-chlorophenyl)but-2-en-1-one exhibiting the highest inhibitory effect on most of the test pathogens. Alternaria 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 beta-trifluoroalkyl aminovinyl ketone fungitoxic derivative.
Gellerman
Gary
G
Department of Biological Chemistry, Ariel University Center of Samaria, Ariel 40700, Israel.
Pariente
Natali
N
Paz
Zahi
Z
Shnaiderman
Anat
A
Yarden
Oded
O
D000528:Alternaria / Q000187:drug effects; D001203:Ascomycota / Q000187:drug effects; D020171:Botrytis / Q000187:drug effects; D002074:Butanones / Q000138:chemical synthesis* / Q000494:pharmacology*; D002082:Butylamines / Q000138:chemical synthesis* / Q000494:pharmacology*; D005658:Fungi / Q000187:drug effects*; D005659:Fungicides, Industrial / Q000138:chemical synthesis* / Q000494:pharmacology*; D009492:Neurospora crassa / Q000187:drug effects; D013329:Structure-Activity Relationship
C546698:3-amino-4,4,4-trifluoro-1-(4-chlorophenyl)but-2-en-1-one; D002074:Butanones; D002082:Butylamines; D005659:Fungicides, Industrial