Dow Agrosciences LLC

Other

Corteva Agriscience LLC

David E Podhorez

Gary A Roth

Beth Lorsbach

Qiang Yang

Gregory T Whiteker

James M Renga

Yuanming Zhu

Joseck M Muhuhi

Scott P West

Xiaoyong Li

Kim Eric Arndt

Ronald Ross, Jr

Yang Cheng

Yu Zhang

Carl Vincent DeAmicis

Kaitlyn C Gray

Ann Marie Buysse

Daniel Knueppel

Thomas L Siddall

Christian Thomas Lowe

John Wesley Hull, Jr

Douglas Bland

Timothy J Adaway

James R McConnell

James R Mcconnell

Duane R Romer

David Craig Molzahn

Brent Jeffrey Rieder

Vidyadhar Babu Hegde

David H Cooper

Jossian Oppenheimer

Erich J Molitor

Christopher Stanley Galka

Neil Vincent Kirby

Emily Jane Canada

Scott Jerome Bis

Mark W Zettler

Mary E Pieczko

Patrick T McGough

Christopher W Derstine

Michael Gullo

John K Swayze

Mary L Ash

Norman R Pearson

Stacie L Santhany

Mark Muehlfeld

Rebecca L Rezac

Christine H Brady

David G Ouimette

Gary L Sampson

Justin A Alberts

Douglas C Bland

Ronald Ross

Timothy Adaway

David C Molzahn

Gary Alan Roth

The present disclosure concerns a method for preparing florasulam which involves treating a solution of 2,6-difluoroaniline in 1,2-propylene glycol with: a) sulfonyl chloride III and then b) a base to provide, after workup and isolation, florasulam (I) in yields of about 65-85%. The treatment of 2,6-difluoroaniline with sulfonyl chloride III and the base are conducted by controlled additions.

Method of preparation of florasulam

This application relates to efficient and economical synthetic chemical processes for the preparation of pesticidal thioethers. Further, the present application relates to certain novel compounds useful in the preparation of pesticidal thioethers. Specifically, this application relates to a process for the preparation of 3-chloro-1H-pyrazol-4-amine and salts thereof. More particularly, this application relates to a process for the preparation of 3-chloro-1H-pyrazol-4-amine and salts thereof by halogenating and reducing 4-nitropyrazole.

Processes for the preparation of pesticide compounds

3-(3-chloro-1H-pyrazol-1-yl)pyridine is prepared by cyclizing 3-hydrazinopyridine-.dihydrochloride with a dialkyl maleate to provide an alkyl 5-oxo-2-(pyridin-3-yl)pyrazolidine-3-carboxylate, by chlorinating to provide an alkyl 3-chloro-1-(pyridin-3-yl)-4,5-dihydro-1H-pyrazole-5-carboxylate, by oxidizing to provide an alkyl 3-chloro-1-(pyridin-3-yl)-1H-pyrazole-5-carboxylate, by converting the ester to the carboxylic acid by hydrolysis to provide 3-chloro-1-(pyridin-3-yl)-1H-pyrazole-5-carboxylic acid hydrochloride, and by removing the carboxylic acid by a decarboxylation reaction.

Process for the preparation of 3-(3-chloro-1H-pyrazol-1-yl)pyridine

3-(3-chloro-1H-pyrazol-1-yl)pyridine is prepared by cyclizing 3-hydrazinopyridine-&#x2022;dihydrochloride with a dialkyl maleate to provide an alkyl 5-oxo-2-(pyridin-3-yl)pyrazolidine-3-carboxylate, by chlorinating to provide an alkyl 3-chloro-1-(pyridin-3-yl)-4,5-dihydro-1H-pyrazole-5-carboxylate, by oxidizing to provide an alkyl 3-chloro-1-(pyridin-3-yl)-1H-pyrazole-5-carboxylate, by converting the ester to the carboxylic acid by hydrolysis to provide 3-chloro-1-(pyridin-3-yl)-1H-pyrazole-5-carboxylic acid hydrochloride, and by removing the carboxylic acid by a decarboxylation reaction.

3-(3-Chloro-1H-pyrazol-1-yl)pyridine is prepared by cyclizing 3-hydrazinopyridine-&#xb7;dihydrochloride with acrylonitrile to provide 1-(pyridin-3-yl)-4,5-dihydro-1H-pyrazol-3-amine, by oxidizing to provide 3-(3-amino-1H-pyrazol-1-yl)pyridine, and by converting the amino group to a chloro group by a Sandmeyer reaction.

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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

3-(3-chloro-1H-pyrazol-1-yl)pyridine is prepared by cyclizing 3-hydrazinopyridine-.dihydrochloride with a dialkyl maleate to provide an alkyl 5-oxo-2-(pyridin-3-yl)pyrazolidine-3-carboxylate, by chlorinating to provide an alkyl 3-chloro-1-(pyridin-3-yl)-4,5-dihydro-1H-pyrazole-5-carboxylate, by oxidizing to provide an alkyl 3-chloro-1-(pyridin-3-yl)-1H-pyrazole-5-carboxylate, by converting the ester to the carboxylic acid by hydrolysis to provide 3-chloro-1 -(pyridin-3-yl)-1H-pyrazole-5-carboxylic acid hydrochloride, and by removing the carboxylic acid by a decarboxylation reaction.

Provided herein are fluoropicolinoyl fluorides and processes for their preparation. In some embodiments, provided herein is a process for the preparation of 5-fluoro-6-aryl-picolinoyl fluorides from chloropicolinoyl chlorides.

Fluoropicolinoyl fluorides and processes for their preparation

3-(3-Chloro-1H-pyrazol-1-yl)pyridine is prepared by cyclizing 3-hydrazinopyridine&#x2022;dihydrochloride with acrylonitrile to provide 1-(pyridin-3-yl)-4,5-dihydro-1H-pyrazol-3-amine, by oxidizing to provide 3-(3-amino-1H-pyrazol-1-yl)pyridine, and by converting the amino group to a chloro group by a Sandmeyer reaction.

3-(3-Chloro-1H-pyrazol-1-yl)pyridine is prepared by cyclizing 3-hydrazinopyridine.dihydrochloride with acrylonitrile to provide 1-(pyridin-3-yl)-4,5-dihydro-1H-pyrazol-3-amine, by oxidizing to provide 3-(3-amino-1H-pyrazol-1-yl)pyridine, and by converting the amino group to a chloro group by a Sandmeyer reaction.

3-(3-chloro-1H-pyrazol-1-yl)pyridine is prepared by cyclizing 3-hydrazinopyridine.dihydrochloride with a dialkyl maleate to provide an alkyl 5-oxo-2-(pyridin-3-yl)pyrazolidine-3-carboxylate, by chlorinating to provide an alkyl 3-chloro-1-(pyridin-3-yl)-4,5-dihydro-1H-pyrazole-5-carboxylate, by oxidizing to provide an alkyl 3-chloro-1-(pyridin-3-yl)-1H-pyrazole-5-carboxylate, by converting the ester to the carboxylic acid by hydrolysis to provide 3-chloro-1-(pyridin-3-yl)-1H-pyrazole-5-carboxylic acid hydrochloride, and by removing the carboxylic acid by a decarboxylation reaction.

Growing community of inventors

Midland, MI, United States of America

David E Podhorez