Stereoselective synthesis and antifungal activities of (E)-alpha-(methoxyimino)benzeneacetate derivatives containing 1,3,5-substituted pyrazole ring.
Thirteen novel (E)-alpha-(methoxyimino)benzeneacetate derivatives, the analogues of strobilurins, which contain two pharmacophoric substructures of the methyl (E)-methoxyiminoacetate moiety and 1,3,5-substituted pyrazole ring, were stereoselectively synthesized. It was found that the coupling reaction could give stereoselectively (E:Z ca. 14:1) the key intermediate material (E)-methyl 2-(hydroxyimino)-2-o-tolyl acetate (2). An X-ray crystallographic structure determination was carried out in a representative product. The preliminary bioassays indicated that all of the compounds 1 showed potent fungicidal activity against Rhizoctonia solani, Botrytis cinereapers, Gibberella zeae, Physalospora piricola, and Bipolaris mayclis.
Li
Yan
Y
Key Laboratory of Synthesis and Application of Organic Functional Molecules of the Education Ministry, Hubei University, Wuhan, Hubei 430062, China. liyanok@hotmail.com
Zhang
Hong-Quan
HQ
Liu
Jie
J
Yang
Xiang-Ping
XP
Liu
Zhao-Jie
ZJ
D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000494:pharmacology*; D018360:Crystallography, X-Ray; D005658:Fungi / Q000187:drug effects; D005659:Fungicides, Industrial / Q000138:chemical synthesis* / Q000494:pharmacology; D007097:Imines / Q000032:analysis* / Q000494:pharmacology; D010648:Phenylacetates / Q000032:analysis* / Q000494:pharmacology; D011720:Pyrazoles / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
C534853:(E)-alpha-(methoxyimino)benzeneacetate; D001555:Benzene Derivatives; D005659:Fungicides, Industrial; D007097:Imines; D010648:Phenylacetates; D011720:Pyrazoles; C031280:pyrazole