RESUMEN
Multiple classes of commercially important auxin herbicides have been discovered since the 1940s including the aryloxyacetates (2,4-D, MCPA, dichlorprop, mecoprop, triclopyr, and fluroxypyr), the benzoates (dicamba), the quinoline-2-carboxylates (quinclorac and quinmerac), the pyrimidine-4-carboxylates (aminocyclopyrachlor), and the pyridine-2-carboxylates (picloram, clopyralid, and aminopyralid). In the last 10 years, two novel pyridine-2-carboxylate (or picolinate) herbicides were discovered at Dow AgroSciences. This paper will describe the structure activity relationship study that led to the discovery of the 6-aryl-picolinate herbicides Arylex™ active (2005) and Rinskor™ active (2010). While Arylex was developed primarily for use in cereal crops and Rinskor is still in development primarily for use in rice crops, both herbicides will also be utilized in additional crops.
Asunto(s)
Descubrimiento de Drogas , Grano Comestible/efectos de los fármacos , Herbicidas/farmacología , Ácidos Indolacéticos/farmacología , Oryza/efectos de los fármacos , Picloram/análogos & derivados , Herbicidas/síntesis química , Herbicidas/química , Ácidos Indolacéticos/síntesis química , Ácidos Indolacéticos/química , Picloram/síntesis química , Picloram/química , Picloram/farmacología , Relación Estructura-ActividadRESUMEN
BACKGROUND: Systemicity is an important attribute of fungicides that is difficult to measure in early-stage screening without labeling the compound with a radioisotope. A method of measuring translocation that does not require potent fungicidal activity or a radiolabel would guide identification of compounds with desirable attributes. RESULTS: The authors developed an analytical technique that mimics field application, using LC-MS/MS to screen compounds for translocation in wheat leaves. The method sorted commercial and experimental fungicides appropriately into systemic and non-systemic categories. A model using LC-MS/MS data was equivalent to a lipophilicity model and superior to a water solubility model at predicting compound systemicity. CONCLUSION: Early-stage compounds can be screened for systemicity on whole plants using LC-MS/MS.