PREPARACIÓN DE ANÁLOGOS HALOGENADOS DE PICLORAM

• Main Authors: Noormohamed M. Niyaz, Gregory T. Whiteker, Devaraj Jayachandran, Zhang Chunming, Aaron A. Shinkle, Abraham D. Schuitman, Ling Rong, Kister Jeremy, Tu Siyu, Nicholas M. Irvine, Ronald B. Leng, Lee Melissa, Ghavtadze Nugzar, Rongrong [Mandy] Lin
• Format: Patent
• Language: Spanish
• Published: 30.04.2020
• Subjects: AGRICULTURE; ANIMAL HUSBANDRY; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES, AS HERBICIDES; CHEMISTRY; FISHING; FORESTRY; HETEROCYCLIC COMPOUNDS; HUMAN NECESSITIES; HUNTING; METALLURGY; ORGANIC CHEMISTRY; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS; PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTSTHEREOF; TRAPPING

Métodos para preparar análogos 5-fluoro-6-(bromo o cloro)picloram, o derivados, a partir del ácido, un éster o el análogo nitrilado de picloram. Incluyen las etapas de: (1) introducir un grupo ftaloílo en sustituyente 4-amino del ácido, éster o análogo nitrilado de picloram; (2) añadir 2 átomos de flúor en posiciones 5,6 del anillo piridínico mediante técnicas de fluoración por intercambio de halógeno, (3) eliminar el grupo ftaloílo, hidrolizar el sustituyente éster o nitrilo y añadir cloro o bromo a la posición 6 mediante tratamiento con ácido y agua, y (4) esterificar el 5-fluoro-6-(bromo o cloro)picloram producido en (3). Methods for preparing 5-fluoro-6-(bromo or chloro)picloram analogs, or derivatives thereof, from picloram acid, picloram ester, or the nitrile analog of picloram are provided. The methods include chemical process steps that: (1) introduce a phthaloyl group onto the 4-amino substituent of picloram acid, picloram ester, or the nitrile analog of picloram, (2) add 2 fluorine atoms at the 5,6-positions of the pyridine ring using halex fluorination chemistry, (3) remove the phthaloyl group, hydrolyze the ester or nitrile substituent, and add chlorine or bromine to the 6-position by treatment with an acid and water, and finally, (4) esterify the 5-fluoro-6-(bromo or chloro)picloram acid produced in step (3) to a 5-fluoro-6-(bromo or chloro)picloram ester.