6-(poly-substituted aryl)-4-aminopicolinates and their use as herbicides

• US 7,498,468 B2
• Filed: 10/04/2007
• Issued: 03/03/2009
• Est. Priority Date: 01/13/2006
• Status: Active Grant

• Current Assignee: Corteva Agriscience LLC (Corteva, Inc.)
• Original Assignee: Dow Agrosciences LLC (Corteva, Inc.)
• Inventors: Siddall, Thomas L., Balko, Terry W., Daeuble, John F.
• Primary Examiner(s): Balasubramanian; Venkataraman
• Application Number:
  US11/906,972
• Publication Number:
  US 20080045734A1
• Time in Patent Office: 516 Days
• Field of Search: 568/1, 568/656, 568/775, 570/127, 570/162, 570/171
• US Class Current: 568/1
• CPC Class Codes: A01N 25/32 Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
• CPC Class Codes: A01N 43/40 six-membered rings
• CPC Class Codes: C07C 211/52 the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
• CPC Class Codes: C07C 217/84 the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
• CPC Class Codes: C07C 233/25 having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
• CPC Class Codes: C07C 233/65 having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
• CPC Class Codes: C07C 25/13 containing fluorine
• CPC Class Codes: C07C 255/50 to carbon atoms of non-condensed six-membered aromatic rings
• CPC Class Codes: C07C 255/54 containing cyano groups and etherified hydroxy groups bound to the carbon skeleton
• CPC Class Codes: C07C 323/09 having sulfur atoms of thio groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
• CPC Class Codes: C07C 39/26 monocyclic monohydroxylic containing halogen bound to ring carbon atoms
• CPC Class Codes: C07C 39/27 all halogen atoms being bound to ring carbon atoms
• CPC Class Codes: C07C 43/225 containing halogen
• CPC Class Codes: C07C 47/55 containing halogen
• CPC Class Codes: C07C 47/575 containing ether groups, groups, groups, or groups
• CPC Class Codes: C07C 49/80 containing halogen
• CPC Class Codes: C07D 213/79 Acids; Esters
• CPC Class Codes: C07F 1/02 Lithium compounds
• CPC Class Codes: C07F 1/08 Copper compounds
• CPC Class Codes: C07F 3/00 Compounds containing elements of Groups 2 or 12 of the Periodic Table
• CPC Class Codes: C07F 3/02 : Magnesium compounds
• CPC Class Codes: C07F 5/025 : Boronic and borinic acid compounds
• CPC Class Codes: C07F 7/2208 : Compounds having tin linked only to carbon, hydrogen and/or halogen

Abstract

4-Aminopicolinic acids having tri- and tetra-substituted aryl substituents in the 6-position, and their amine and acid derivatives, are potent herbicides demonstrating a broad spectrum of weed control.

Claims

1. A compound of the formula

ArMetal

wherein

Ar represents a polysubstituted aryl group selected from the group consisting of

a)

2. A compound according to claim 1 selected from the group consisting of:

2-(4-Chloro-2-fluoro-3-methoxyphenyl)-[1,3,2]-dioxaborinane;

2-(4-Chloro-2-fluoro-5-methoxyphenyl)-[1,3,2]-dioxaborinane;

2-(4-Chloro-2-fluoro-3-ethoxyphenyl)-[1,3,2]-dioxaborinane;

2-(4-Chloro-2-fluoro-3-(methylthio)phenyl)-[1,3,2]-dioxaborinane;

2-(4-Chloro-2-fluoro-3-methoxymethylphenyl)-[1,3,2]-dioxaborinane;

2-(4-Chloro-2-fluoro-3-isopropoxyphenyl)-[1,3,2]-dioxaborinane;

2-(4-Chloro-2-fluoro-3-difluoromethylphenyl)-[1,3,2]-dioxaborinane;

2-(4-Chloro-2-fluoro-3-fluoromethylphenyl)-[1,3,2]-dioxaborinane;

4-[1,3,2]-Dioxaborinan-2-yl-3-fluoro-2-methoxybenzonitrile;

2-(4-Chloro-2-fluoro-3-methoxyethoxyphenyl)-[1,3,2]-dioxaborinane;

2-(2,4-Dichloro-3-ethoxyphenyl)-[1,3,2]-dioxaborinane;

2-[4-Chloro-2-fluoro-3-(2,2-difluoroethoxyphenyl]-[1,3,2]-dioxaborinane;

2-(4-Chloro-2-fluoro-5-ethoxyphenyl)-[1,3,2]-dioxaborinane;

2-(2,4-Dichloro-3-(methylthio)phenyl)-[1,3,2]dioxaborinane;

2-Fluoro-3,4-methylenedioxyphenylboronic acid;

2-Fluoro-3-methoxy-4-methylphenylboronic acid;

4-Bromo-2-fluoro-3-methoxyphenylboronic acid;

2-(2-Fluoro-3,4-methylenedioxyphenyl)-[1,3,2]-dioxaborinane;

4-Chloro-3-(diethylamino)-2-fluorophenylboronic acid;

2,4-Dichloro-3-dimethylaminophenylboronic acid;

2-Chloro-4-fluoro-3-methoxyphenylboronic acid;

[3-Chloro-2-fluoro-3-(4,4,5,5-tetramethyl-{1,3,2}dixoborolan-2-yl)-phenyl methyl;

(2-Fluoro-3-methoxy-4-trifluoromethylphenyl)trimethyl stannane;

(3-Butoxy-4-chloro-2-fluorophenyl)trimethyl stannane; and

4-Chloro-2-fluoro-3-(1-fluoro-1-methylethyl)trimethyl stannane.