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

• US 20070179060A1
• Filed: 01/12/2007
• Published: 08/02/2007
• Est. Priority Date: 01/13/2006
• Status: Active Grant

• Current Assignee: Corteva Agriscience LLC (Corteva, Inc.)
• Original Assignee: Dow Agrosciences LLC (Corteva, Inc.)
• Inventors: Balko, Terry, Siddall, Thomas, Daeuble, John, Yerkes, Carla, Schmitzer, Paul
• Granted Patent: US 7,314,849 B2
• Time in Patent Office: Days
• US Class Current: 504/193
• 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 I

2. A compound of claim 1 in which R₁ and R₂ represent H.

3. A compound of claim 1 in which Q₁ represents H.

4. A compound of claim 1 in which Q₂ represents Cl.

5. A compound of claim 1 in which Q₁ represents H and Q₂ represents Cl.

6. A compound of claim 1 in which Ar represents

7. A compound of claim 6 in which W₁ represents Cl or F.

8. A compound of claim 6 in which X₁ represents C₁-C₄ alkoxy, C₁-C₄ alkylthio, C₁-C₄ haloalkyl or —

NR₃R₄.

9. A compound of claim 6 in which Y₁ represents Cl, Br or —

CF₃.

10. A compound of claim 1 in which Ar represents

11. A compound of claim 10 in which X₂ represents C₁-C₄ alkoxy, C₁-C₄ alkylthio, C₁-C₄ haloalkyl or —

NR₃R₄.

12. A compound of claim 10 in which Y₂ represents Cl, Br or —

CF₃.

13. A compound of claim 1 in which Ar represents

14. A compound of claim 13 in which Y₃ represents Cl, Br or —

CF₃.

15. A compound of claim 13 in which Z₃ represents C₁-C₄ alkoxy, C₁-C₄ alkylthio, C₁-C₄ haloalkyl or —

NR₃R₄.

16. A herbicidal composition comprising an herbicidally effective amount of a compound of Formula I, according to claim 1, in admixture with an agriculturally acceptable adjuvant or carrier.

17. A method of controlling undesirable vegetation which comprises contacting the vegetation or the locus thereof with or applying to the soil to prevent the emergence of vegetation an herbicidally effective amount of a compound of Formula I, according to claim 1.

18. A compound of the formula

ArL

wherein

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

19. A compound according to claim 18 selected from the group consisting of:

3-Bromo-6-chloro-2-fluorophenol;

3-Bromo-2-fluoro-6-trifluoromethylphenol;

3-Bromo-2-chloro-6-fluorophenol;

1-Bromo-4-chloro-2-fluoro-3-methoxybenzene;

1-Bromo-4-chloro-3-ethoxy-2-fluorobenzene;

1-Bromo-4-chloro-2-fluoro-3-isopropropoxybenzene;

1-Bromo-4-chloro-2-fluoro-3-(2-methoxyethoxy) benzene;

1-Bromo-2-fluoro-3-methoxy-4-trifluoromethylbenzene;

1-Bromo-2,4-dichloro-3-ethoxybenzene;

1-Bromo-3-butoxy-4-chloro-2-fluorobenzene;

1-Bromo-4-chloro-2-fluoro-3-methoxymethoxybenzene;

1-Bromo-2-chloro-4-fluoro-3-methoxybenzene;

1-Bromo-4-chloro-2-fluoro-3-difluoromethoxybenzene;

1-Bromo-4-chloro-3-(2,2-difluoroethoxy)-2-fluorobenzene;

1-Bromo-2,4-dichloro-3-(2,2-difluoroethoxy)benzene;

1-Bromo-4-chloro-2-fluoro-3-(methylthio)benzene;

1-Bromo-2,4-dichloro-3-(methylthio)benzene;

1-(3-Bromo-6-chloro-2-fluorophenyl)-1-ethanol;

3-Bromo-2,4-dichlorobenzaldehyde;

1-(3-Bromo-2,6-dichlorophenyl)-1-ethanol;

1-Bromo-4-chloro-3-ethyl-2-fluoro-benzene;

1-(3-Bromo-6-chloro-2-fluoro-phenyl)-2,2,2-trifluoroethanone;

1-(3-Bromo-6-chloro-2-fluorophenyl)-1-propanol;

2-(3-Bromo-6-chloro-2-fluorophenyl)-2-propanol;

1-Bromo-4-chloro-2-fluoro-3-difluoromethylbenzene;

1-Bromo-2,4-dichloro-3-difluoromethylbenzene;

1-Difluoromethyl-3-fluoro-4-iodo-2-methoxybenzene;

N-Pivaloyl-2-bromo-4-chloro-3-methoxyaniline;

2-Bromo-4-chloro-1-iodo-3-methoxybenzene;

4-Chloro-2,6-difluoro-5-methyl-1-iodobenzene;

2-Chloro-4-difluoromethyl-3-methoxy-1-iodobenzene;

1-Chloro-2-difluoromethyl-3,5-difluoro-4-iodobenzene;

1-(3-Bromo-6-chloro-2-fluorophenyl)-2,2,2-trifluoroethanol;

3-Fluoro-4-iodo-2-methoxyphenyl methanol;

1-Bromo-4-chloro-3-fluoromethyl-2-fluorobenzene;

1-Bromo-4-chloro-2-fluoro-3-(1-fluoro-1-methylethyl)benzene;

1-Bromo-2,4-dichloro-3-(1-fluoroethyl)benzene;

1-Bromo-4-chloro-2-fluoro-3-(1-fluoroethyl)benzene;

1-Bromo-4-chloro-2-fluoro-3-(1,2,2,2-tetrafluoroethyl)benzene;

1-Bromo-4-chloro-2-fluoro-3-(1-fluoropropyl)benzene;

2-Fluoro-4-fluoromethyl-1-iodo-3-methoxybenzene;

1-Bromo-4-chloro-2-fluoro-3-methoxymethylbenzene;

1-Bromo-4-chloro-2-fluoro-3-methylbenzene;

3-Bromo-6-chloro-2-fluorobenzonitrile;

3-Bromo-2-fluoro-6-chlorobenzamide;

3-Bromo-6-chloro-2-fluoroaniline;

3-Bromo-2,6-dichloroaniline;

N-(3-Bromo-6-chloro-2-fluorophenyl)-N,N-dimethylamine;

N-(3-Bromo-6-chloro-2-fluorophenyl)-N,N-diethylamine;

N-(3-Bromo-2,6-dichlorophenyl)-N,N-dimethylamine;

N-(3-Bromo-6-chloro-2-fluorophenyl)-N-methylamine;

1,3-Difluoro-2-iodo-4-methoxy-5-methylbenzene;

3,5-Difluoro-4-iodo-2-methoxybenzonitrile;

N-(6-Chloro-2,4-difluoro-3-iodophenyl)-N,N-dimethylamine;

1,3-Dichloro-5-fluoro-4-iodo-2-methoxybenzene;

1,3-Difluoro-2-iodo-4-methoxy-5-methylbenzene;

2,3-Difluoro-4-iodobenzonitrile;

3-Chloro-1-difluoromethyl-5-fluro-4-iodo-2-methoxybenzene;

2-Ethoxy-1,3-difluoro-4-iodobenzene;

1,3-Difluoro-2-iodo-4-methoxy-5-methylbenzene;

3,5 Difluoro-4-iodo-2-methoxybenzonitrile;

1-Chloro-3,5-difluoro-4-iodo-2-methoxybenzene;

1-Chloro-2-ethoxy-3,5-difluoro-4-iodobenzene;

3-Fluoro-4-iodo-2-methoxybenzonitrile;

3-Fluoro-4-iodo-2-methoxybenzaldehyde;

3-Chloro-4-iodo-2-methoxyaniline;

1-Bromo-3-chloro-4-iodo-2-methoxybenzene;

(6-Chloro-2,4-difluoro-3-iodophenyl)dimethylamine;

2,4,6-Trifluoro-3-iodobenzonitrile;

1-Bromo-3,5-difluoro-4-iodo-2-methoxybenzene;

1,3-Dichloro-5-fluoro-4-iodo-2-methoxybenzene;

6-Chloro-2,4-difluoro-3-iodobenzaldehyde;

1-Bromo-2,4-difluoro-5-methoxybenzene; and

2-Chloro-4,6-difluoro-1-iodo-3-methoxybenzene.

20. A compound of the formula

ArMetal

wherein

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

21. A compound according to claim 20 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.