Synthesis and herbicidal activity of phenyl-substituted benzoylpyrazoles.
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.
Siddall
Thomas L
TL
Dow AgroSciences LLC, 9330 Zionsville Rd, Indianapolis, IN 46268-1054, USA.
Ouse
David G
DG
Benko
Zoltan L
ZL
Garvin
Gail M
GM
Jackson
Johnny L
JL
McQuiston
Jeffrey M
JM
Ricks
Michael J
MJ
Thibault
Thomas D
TD
Turner
James A
JA
Vanheertum
John C
JC
Weimer
Monte R
MR
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
D006540:Herbicides; D011720:Pyrazoles; D015111:4-Hydroxyphenylpyruvate Dioxygenase