Dow Agrosciences LLC

Union Carbide Chemicals & Plastics Technology Corporation

Univation Technologies, LLC

Dow Global Technolgoies LLC

Corteva Agriscience LLC

Vps-3, Inc.

Other

Gregory T Whiteker

James M Renga

Yuanming Zhu

Gary A Roth

Carl Vincent DeAmicis

Joseck M Muhuhi

Qiang Yang

Beth Lorsbach

Yu Zhang

Kaitlyn C Gray

Nakyen Choy

Kim Eric Arndt

David E Podhorez

Daniel Knueppel

Thomas P Clark

Christian Thomas Lowe

Michael R Loso

Richard Brewer Rogers

Jim Xinpei Huang

Benjamin M Nugent

Ronald Ross, Jr

Noormohamed Mohamed Niyaz

Peter Lee Johnson

Michael Thomas Sullenberger

Xiaoyong Li

William Joel Hoekstra

Thomas L Siddall

David James Schreck

Ann Marie Buysse

Frederick John Karol

Jerzy Klosin

Paul R Schmitzer

Jeffrey S Nissen

Timothy Todd Wenzel

Walter Thomas Reichle

Zoltan Laszlo Benko

Yang Cheng

Matthias Stefan Ober

Mark Gregory Goode

Roger L Kuhlman

Carla Nanette Yerkes

John Francis Szul

Gary D Crouse

John Robert Briggs

Norbert M Satchivi

Thomas Clarence Sparks

Joseph D Eckelbarger

Arkady L Krasovskiy

Scott P West

Elisabeth J Kane

Belgin Canturk

John F Daeuble, Sr

Peter S Borromeo

Nicholas R Babij

Christopher Galliford

Patrick S Hanley

Nneka Tuere Breaux

Siyu Tu

Kenneth E Stockman

Jim M Renga

Gary David Gustafson

Clark Curtis Williams

Thomas Henry Peterson

Chunming Zhang

John Henry Oskam

Jeremy Kister

Ronald B Leng

Rong Ling

Nicholas Martin Irvine

Abraham D Schuitman

Yan Hao

James E Babin

Purna Chand Sishta

Jayachandran Devaraj

Tina Staton

Nugzar Ghavtadze

Natalie Christine Giampietro

Simon Mawson

David Laitar

Robert D J Froese

Lindsey Gayle Fischer

Erich W Baum

George N Foster

Timothy A Boebel

Tae Hoon Kwalk

Kersten Anne Terry

Fangzheng Li

Matthew Gary McKee

Erich J Molitor

Matthew Lee Grandbois

Jeff Petkus

Robert Harold Vogel

Robert Froese

Scott Hanley Wasserman

John F Daeuble

Day-Chyuan Lee

Carl DeAMICIS

Eric Lucas

Tong Chen

The present technology relates to processes, mixtures and intermediates useful for making picolinamide fungicides. The picolinamide compounds are prepared by processes that include coupling together a 4-methoxy-3-acyloxypicolinic acid with key 2-amino-L-alaninate esters derived from substituted 2-phenylethanols.

Process for synthesis of picolinamides

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.

Preparation of halogen analogs of picloram

4-Alkoxy-3-hydroxypicolinic acids may be conveniently prepared from 4,6-dibromo-3-hydroxypicolinonitrile in a series of chemical steps selected from bromo substitution, nitrile hydrolysis and halogen reduction that are conducted as a single pot process. 4,6-Dibromo-3-hydroxypicolinonitrile may be prepared from furfural in a series of chemical steps selected from cyano-amination, amine salt formation and bromination-rearrangement.

Processes for the preparation of 4-alkoxy-3-hydroxypicolinic acids

Provided herein is a process for the preparation of 4-((6-(2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)pyridin-3-yl)oxy)benzonitrile.

4-((6-(2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propyl)pyridin-3-yl and processes of preparation

A fungicidal 4-methoxy-3-acetyloxypicolinamide may be conveniently prepared in processes that include the coupling together of 4-methoxy-3-acetyloxypicolinic acid or 4-methoxy-3-hydroxypicolinic acid with a key 2-aminopropanoate ester derived from a 1,1-bis(4-fluorophenyl)propane-1,2-diol.

Processes for the preparation of 4-alkoxy-3-(acyl or alkyl)oxypicolinamdes

The present application provides processes for making pesticidal compounds and compounds useful both as pesticides and in the making of pesticidal compounds.

Processes for the preparation of pesticidal compounds

Provided herein are 2-(2,4-difluorophenyl)-1,1-difluoro-1-(5-substituted-pyridin-2-yl)-3-(1H-tetrazol-1-yl)propan-2-ols and 1-(2,4-difluorophenyl)-2,2-difluoro-2-(5-substituted-pyridin-2-yl)ethanones and processes for their preparation.

2-(2,4-difluorophenyl)-1,1-difluoro-1-(5-substituted-pyridin-2-yl)-3-(1h-tetrazol-1-yl)propan-2-ols and processes for their preparation

4-Alkoxy-3-hydroxypicolinic acids may be conveniently prepared from 4,6-dibromo-3-hydroxypicolinonitrile in a series of chemical steps selected from bromo substitution, nitrile hydrolysis and halogen reduction that are conducted as a single pot process. 4,6-Dibromo-3-hydroxypicolinonitrile may be prepared from furfural in a series of chemical steps selected from cyano-amination, amine salt formation and bromination-rearrangement. 4-Alkoxy-3-acetoxypicolinic acids may be conveniently prepared from 4-alkoxy-3-hydroxypicolinic acids by treatment with acetic anhydride.

Process for the preparation of 4-alkoxy-3-acetoxypicolinic acids

Processes for the preparation of 4-alkoxy-3-(acyl or alkyl)oxypicolinamides

2-(2,4-difluorophenyl)-1,1-difluoro-1-(5-substituted-pyridin-2-yl)-3-(1H-tetrazol-1-yl)propan-2-ols and processes for their preparation

4-Amino-5-fluoro-3-chloro-6-(substituted)picolinates are prepared from trifluoroacetic acid, p-methoxyaniline, a 3,3-dialkoxyprop-1-yne and a substituted methylene amine by a series of steps.

Process for the preparation of 4-amino-5-fluoro-3-chloro-6-(substituted)picolinates

4-Alkoxy-3-hydroxypicolinic acids may be conveniently prepared from 2-hydroxypicolinonitrile in a series of chemical steps selected from chlorination, chloro substitution, nitrile hydrolysis and chloro reduction.

Process for the preparation of 4-alkoxy-3-hydroxypicolinic acids

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Carmel, IN, United States of America

Gregory T Whiteker