Stereoselective synthesis and fungicidal activities of (E)-alpha-(methoxyimino)-benzeneacetate derivatives containing 1,3,4-oxadiazole ring.
Fifteen novel (E)-alpha-(methoxyimino)-benzeneacetate derivatives, the analogues of strobilurins, which contain two pharmacophoric substructures of (E)-methyl methoxyiminoacetate moiety and 1,3,4-oxadiazole ring were stereoselectively synthesized. It was first found that the coupling reaction could give stereoselectively the key intermediate (E) and (Z)-methyl 2-(hydroxyimino)-2-o-tolylacetate 2 with a ratio of 14:1. The preliminary bioassays indicated that all the compounds 1 showed potent fungicidal activity against Rhizoctonia solani, Botrytis cinereapers, Gibberella zeae, Physalospora piricola and Bipolaris mayclis, and all of the tested compounds 1a-1o had more potent fungicidal activities against R. solani than Kresoxim-methyl.
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
Liu
Jie
J
Zhang
Hongquan
H
Yang
Xiangping
X
Liu
Zhaojie
Z
D000085:Acetates / Q000138:chemical synthesis; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000494:pharmacology; D005658:Fungi / Q000187:drug effects*; D008826:Microbial Sensitivity Tests; D010069:Oxadiazoles / Q000138:chemical synthesis; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000085:Acetates; D000935:Antifungal Agents; D001555:Benzene Derivatives; D010069:Oxadiazoles