Novel 4-aminopyridine and 6-aminopyrimidine carboxylates as herbicides

A C1-C6, alkyl technology, applied in the field of new 4-aminopyridine and 6-aminopyrimidine carboxylate as herbicides, can solve problems such as affecting crop yields

Inactive Publication Date: 2015-12-30
DOW AGROSCIENCES LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Weeds compete with crops ...

Method used

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  • Novel 4-aminopyridine and 6-aminopyrimidine carboxylates as herbicides
  • Novel 4-aminopyridine and 6-aminopyrimidine carboxylates as herbicides
  • Novel 4-aminopyridine and 6-aminopyrimidine carboxylates as herbicides

Examples

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preparation example Construction

[0186] Compound preparation method

[0187] Exemplary methods for the synthesis of compounds of formula (I) are provided below.

[0188] 3,5-Disubstituted-4-amino-6-(optionally substituted phenyl or pyridyl)pyridine-2-carboxylic acids of formula (I) can be prepared in various ways. As shown in Scheme I, 4-amino-6-chloro-pyridine-2-carboxylates of formula (II) can be prepared via Suzuki coupling with boronic acids or esters in a base such as potassium fluoride and a catalyst such as bis(tris Phenylphosphine)-palladium(II) dichloride in the presence of a polar protic solvent mixture such as acetonitrile-water at a temperature of for example 110° C., for example, in a microwave reactor into the 4-amino- 6-substituted-pyridine-2-carboxylates, wherein Ar is as defined herein (reaction a 1 ). 4-Amino-6-substituted-pyridine-2-carboxylates of formula (III) can be converted to phosphonates of formula (IV) via reaction with iodinating reagents such as periodic acid and iodine in a po...

Embodiment 1

[0229] Example 1: Preparation of 4-amino-3,6-dichloro-pyridine-2-carboxylic acid methyl ester (head A)

[0230]

[0231] Prepared as described in Fields et al., WO2001051468A1.

Embodiment 2

[0232] Example 2: Preparation of 4-amino-3,6-dichloro-5-fluoro-pyridine-2-carboxylic acid methyl ester (head B)

[0233]

[0234] Prepared as described in Fields et al., Tetrahedron Letters 2010, 51, 79-81.

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Abstract

4-Amino-6-(pyridyl and 2-substitutedphenyl)-picolinic acids and their derivatives; 6- amino-2-(pyridyl and 2-substitutedphenyl)-pyrimidine-4-carboxylates and their derivatives; and methods of using the same as herbicides.

Description

[0001] Cross-references to related applications [0002] This application claims the benefit of U.S. Provisional Application 61 / 791,892 filed on March 15, 2013, and the disclosed contents of 61 / 791,892 are expressly incorporated into this application by reference. Background technique [0003] The development of undesirable vegetation such as weeds is an ongoing problem that farmers encounter on crops, pastures and other sites. Weeds compete with crops and adversely affect crop yields. The use of chemical herbicides is an important tool in controlling undesirable vegetation. [0004] There remains a need for new chemical herbicides that have a broader spectrum of weed control, selectivity, minimal crop damage, storage stability, ease of handling, increased anti-weed activity and / or It is a means to address the development of herbicide resistance to currently used herbicides. Contents of the invention [0005] This application provides compounds of formula (I): [0006] ...

Claims

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Application Information

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IPC IPC(8): A01N43/40C07D401/04
CPCA01N43/40A01N43/54
Inventor J·D·埃克尔巴杰J·B·埃普L·G·费希尔N·C·詹彼得罗J·基斯特J·佩特库斯J·罗思N·M·萨奇维P·R·施米策T·L·西多尔C·N·耶基斯
Owner DOW AGROSCIENCES LLC
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