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

1. A compound of the formula

ArMetal

wherein

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

a)

wherein

W 1 represents halogen;

X 1 represents F, Cl, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxy-substituted C 1 -C 4 alkyl, C 1 -C 4 alkoxy-substituted C 1 -C 4 alkoxy, —CN, —NR 3 R 4 or fluorinated acetyl or propionyl;

Y 1 represents C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, halogen or —CN, or, when X 1 and Y 1 are taken together, represents —O(CH 2 ) n O— wherein n=1 or 2; and

R 3 and R 4 independently represent H or C 1 -C 4 alkyl;

b)

wherein

W 2 represents F or Cl;

X 2 represents F, Cl, —CN, —NO 2 , C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxy-substituted C 1 -C 4 alkyl, C 1 -C 4 alkoxy-substituted C 1 -C 4 alkoxy, —NR 3 R 4 or fluorinated acetyl or propionyl;

Y 2 represents halogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl or —CN, or, when W 2 represents F, X 2 and Y 2 taken together represent —O(CH 2 ) n O— wherein n=1 or 2; and

R 3 and R 4 independently represent H or C 1 -C 6 alkyl; and

c)

wherein

Y 3 represents halogen, —CN or —CF 3 ;

Z 3 represents F, Cl, —CN, —NO 2 , C 1 -C 4 alkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, C 1 -C 4 haloalkyl, C 1 -C 4 haloalkoxy, C 1 -C 4 alkoxy-substituted C 1 -C 4 alkyl, C 1 -C 4 alkoxy-substituted C 1 -C 4 alkoxy, —NR 3 R 4 or fluorinated acetyl or propionyl; and

R 3 and R 4 independently represent H, or C 1 -C 6 alkyl; and

Metal represents Mg-halide, Zn-halide, tri-(C 1 -C 4 alkyl)tin, lithium, copper, or B(OR 8 )(OR 9 ), where R 8 and R 9 are independent of one another, hydrogen, C 1 -C 4 alkyl, or when taken together form an ethylene or propylene group.

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.