title: Semisynthesis and antifungal activity of novel oxime ester derivatives of carabrone modified at C(4) against Botrytis cinerea.
abstract: To continuously improve the potential utility of the natural lead compound of carabrone in agrochemistry, carabrone oxime and 36 novel oxime ester derivatives of carabrone modified at C(4) were synthesized, and evaluated for their antifungal activities against Botrytis cinerea in vitro and in vivo. Of these 36 oxime ester derivatives, some compounds exhibited antifungal activities in vitro or in vivo. It was found that compounds with a pyridinyl residue can either efficiently inhibit spore germination or efficiently inhibit hyphal growth of B. cinerea, and compound 9 exhibited the highest activity in vitro and in vivo with IC50 and EC50 values of 1.17 and 12.9 μg/ml, respectively. Further, the structure-activity relationships are also discussed.
authors.affiliation: Research & Development Center of Biorational Pesticide, Key Laboratory of Plant Protection Resources and Pest Management of Ministry of Education, Northwest A&F University, Yangling 712100, P. R. China (phone: +86-29-87092122; fax: +86-29-87093344 or phone: +86-29-87091884; fax: +86-29-87092122).
authors.forename: Delong
authors.initials: D
authors.lastname: Wang
authors.forename: Shuangxi
authors.initials: S
authors.lastname: Ren
authors.forename: Hao
authors.initials: H
authors.lastname: Wang
authors.forename: He
authors.initials: H
authors.lastname: Yan
authors.forename: Juntao
authors.initials: J
authors.lastname: Feng
authors.forename: Xing
authors.initials: X
authors.lastname: Zhang
mesh_terms: D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D020171:Botrytis / Q000187:drug effects*; D004305:Dose-Response Relationship, Drug; D004952:Esters / Q000737:chemistry / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D010091:Oximes / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: D000935:Antifungal Agents; D004952:Esters; D010091:Oximes
keywords: Antifungal activity; Carabrone; Oxime ester derivatives; Structureactivity relationship (SAR)