title: Quantitative structure-antifungal activity relationships of some benzohydrazides against Botrytis cinerea.
abstract: Fourteen benzohydrazides have been synthesized and evaluated for their in vitro antifungal activity against the phytopathogenic fungus Botrytis cinerea. The best antifungal activity was observed for the N',N'-dibenzylbenzohydrazides 3b-d and for the N-aminoisoindoline-derived benzohydrazide 5. A quantitative structure-activity relationship (QSAR) study has been developed using a topological substructural molecular design (TOPS-MODE) approach to interpret the antifungal activity of these synthetic compounds. The model described 98.3% of the experimental variance, with a standard deviation of 4.02. The influence of an ortho substituent on the conformation of the benzohydrazides was investigated by X-ray crystallography and supported by QSAR study. Several aspects of the structure-activity relationships are discussed in terms of the contribution of different bonds to the antifungal activity, thereby making the relationships between structure and biological activity more transparent.
authors.affiliation: Departamento de Química OrgAnica, Facultad de Ciencias, Universidad de CAdiz, Apartado 40, 11510 Puerto Real, CAdiz, Spain.
authors.forename: José L
authors.initials: JL
authors.lastname: Reino
authors.forename: Liane
authors.initials: L
authors.lastname: Saiz-Urra
authors.forename: Rosario
authors.initials: R
authors.lastname: Hernandez-Galan
authors.forename: Vicente J
authors.initials: VJ
authors.lastname: Aran
authors.forename: Peter B
authors.initials: PB
authors.lastname: Hitchcock
authors.forename: James R
authors.initials: JR
authors.lastname: Hanson
authors.forename: Maykel Perez
authors.initials: MP
authors.lastname: Gonzalez
authors.forename: Isidro G
authors.initials: IG
authors.lastname: Collado
mesh_terms: D000215:Acylation; D020171:Botrytis / Q000187:drug effects*; D018360:Crystallography, X-Ray; D005659:Fungicides, Industrial / Q000737:chemistry* / Q000494:pharmacology*; D006834:Hydrazines / Q000737:chemistry* / Q000494:pharmacology*; D015394:Molecular Structure; D021281:Quantitative Structure-Activity Relationship
chemical_list: D005659:Fungicides, Industrial; D006834:Hydrazines