Stereoselective Synthesis and Antifungal Activities of (E)-α-(Methoxyimino)benzeneacetate Derivatives Containing 1,3,5-Substituted Pyrazole Ring

Abstract

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.

Immunoassays for trifloxystrobin analysis. Part I. Rational design of regioisomeric haptens and production of monoclonal antibodies

“…26 (synthesized in the laboratory following the procedure described by Li et al,9,10 90 mg, 0.466 mmol), tertbutyl 6-bromohexanoate (117 mg, 0.466 mmol), and anhydrous Cs2CO3 (228 mg, 0.699 mmol) in dry DMF (1.7 mL) was stirred under nitrogen for 4 h, poured into water and worked up as usual using EtOAc to extract. Chromatography of the crude product, using hexane-EtOAc (9:1) as eluent, afforded the corresponding O-alkylated oxime 27 (141 mg, 83%) as a colorless oil.…”

Design, Synthesis and Antifungal Activities of Novel Strobilurin Derivatives Containing Pyrimidine Moieties

“…15,16,18 Pyrimidine derivatives widely existing in nature usually have excellent biological activity.…”

Design, Synthesis and Bioactivities of Novel Dichloro-Allyloxy-Phenol-Containing Pyrazole Oxime Derivatives

“…Pyrazole oximes are an important class of heterocyclic compounds which have drawn intense attention because of their good fungicidal [1,2], insecticidal [3][4][5], acaricidal [6], and anti-tobacco mosaic virus (TMV) activity [7]. For instance, Fenpyroximate (Figure 1), a potent agricultural acaricide with a vital pyrazole oxime backbone in the structure, possesses wonderful acaricidal property against some phytophagous mites such as Polyphagotarsonemus latus Banks and Tetranychus urticae Koch on different crops [8].…”