title: Synthesis and herbicidal activity of phenyl-substituted benzoylpyrazoles.
abstract: A novel series of substituted 3-phenyl benzoylpyrazoles were prepared and tested as potential grass herbicides. The targeted materials were prepared by three newly developed synthetic routes, which allowed a comprehensive study of the SAR (structure-activity relationships) of this series. The best combination of grass weed activity (Avena fatua L, Setaria viridis (L) Beauv and Alopecurus myosuroides Huds) and wheat selectivity was obtained with an alkoxy group in the 4-position of the phenyl ring. Activity was further enhanced by the presence of tert-butyl on the pyrazole and a methyl group at the C-2 position of the benzoyl moiety. The alkoxy-substituted 3-phenylbenzoylpyrazoles are a novel class of herbicides with potential utility for control of important grass weeds in cereals.
authors.affiliation: Dow AgroSciences LLC, 9330 Zionsville Rd, Indianapolis, IN 46268-1054, USA.
authors.forename: Thomas L
authors.initials: TL
authors.lastname: Siddall
authors.forename: David G
authors.initials: DG
authors.lastname: Ouse
authors.forename: Zoltan L
authors.initials: ZL
authors.lastname: Benko
authors.forename: Gail M
authors.initials: GM
authors.lastname: Garvin
authors.forename: Johnny L
authors.initials: JL
authors.lastname: Jackson
authors.forename: Jeffrey M
authors.initials: JM
authors.lastname: McQuiston
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Ricks
authors.forename: Thomas D
authors.initials: TD
authors.lastname: Thibault
authors.forename: James A
authors.initials: JA
authors.lastname: Turner
authors.forename: John C
authors.initials: JC
authors.lastname: Vanheertum
authors.forename: Monte R
authors.initials: MR
authors.lastname: Weimer
mesh_terms: D015111:4-Hydroxyphenylpyruvate Dioxygenase / Q000037:antagonists & inhibitors; D006540:Herbicides / Q000138:chemical synthesis / Q000633:toxicity*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D006109:Poaceae / Q000187:drug effects; D011720:Pyrazoles / Q000138:chemical synthesis / Q000633:toxicity*; D013329:Structure-Activity Relationship
chemical_list: D006540:Herbicides; D011720:Pyrazoles; D015111:4-Hydroxyphenylpyruvate Dioxygenase