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US 2007/0179060 A1Published application
6-(Poly-substituted aryl)-4-aminopicolinates and their use as herbicides
AssigneeDow AgroSciences LLC
InventorsTerry Balko, Paul Schmitzer, John Daeuble, Carla Yerkes, Thomas Siddall
Life of this patent
Estimating the term…
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.
Claims21
A compound of the formula I
- wherein
- Q1 represents H or F;
- Q2 represents a halogen with the proviso that when Q1 is H then Q2 is Cl or Br;
- R1 and R2 independently represent H, C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, hydroxy, C1-C6 alkoxy, amino, C1-C6 acyl, C1-C6 carboalkoxy, C1-C6 alkylcarbamyl, C1-C6 alkylsulfonyl, C1-C6 trialkylsilyl or C1-C6 dialkyl phosphonyl or R1 and R2 taken together with N represent a 5- or 6-membered saturated ring;
- and
- Ar represents a polysubstituted aryl group selected from the group consisting of
- wherein
- W1 represents halogen;
- X1 represents F, Cl, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy-substituted C1-C4 alkyl, C1-C4 alkoxy-substituted C1-C4 alkoxy, —CN, —NR3R4 or fluorinated acetyl or propionyl;
- Y1 represents C1-C4 alkyl, C1-C4 haloalkyl, halogen or —CN, or, when X1 and Y1 are taken together, represents —O(CH2)nO— wherein n=1 or 2;
- and
- R3 and R4 independently represent H or C1-C4 alkyl;
- wherein
- W2 represents F or Cl;
- X2 represents F, Cl, —CN, —NO2, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy-substituted C1-C4 alkyl, C1-C4 alkoxy-substituted C1-C4 alkoxy, —NR3R4 or fluorinated acetyl or propionyl;
- Y2 represents halogen, C1-C4 alkyl, C1-C4 haloalkyl or —CN, or, when W2 represents F, X2 and Y2 taken together represent —O(CH2)nO— wherein n=1 or 2;
- and
- R3 and R4 independently represent H or C1-C6 alkyl;
- and
- wherein
- Y3 represents halogen, —CN or —CF3;
- Z3 represents F, Cl, —CN, —NO2, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy-substituted C1-C4 alkyl, C1-C4 alkoxy-substituted C1-C4 alkoxy, —NR3R4 or fluorinated acetyl or propionyl;
- and
- R3 and R4 independently represent H, or C1-C6 alkyl;
- and agriculturally acceptable derivatives of the carboxylic acid group.
22 more elements
A compound of the formula
- ArL
- wherein
- Ar represents a polysubstituted aryl group selected from the group consisting of
- wherein
- W1 represents halogen;
- X1 represents F, Cl, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy-substituted C1-C4 alkyl, C1-C4 alkoxy-substituted C1-C4 alkoxy, —CN, —NR3R4 or fluorinated acetyl or propionyl;
- Y1 represents C1-C4 alkyl, C1-C4 haloalkyl, halogen or —CN, or, when X1 and Y1 are taken together, represents —O(CH2)nO— wherein n=1 or 2;
- and
- R3 and R4 independently represent H or C1-C4 alkyl;
- wherein
- W2 represents F or Cl;
- X2 represents F, Cl, —CN, —NO2, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy-substituted C1-C4 alkyl, C1-C4 alkoxy-substituted C1-C4 alkoxy, —NR3R4 or fluorinated acetyl or propionyl;
- Y2 represents halogen, C1-C4 alkyl, C1-C4 haloalkyl or —CN, or, when W2 represents F, X2 and Y2 taken together represent —O(CH2)nO— wherein n=1 or 2;
- and
- R3 and R4 independently represent H or C1-C6 alkyl;
- and
- wherein
- Y3 represents halogen, —CN or —CF3;
- Z3 represents F, Cl, —CN, —NO2, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy-substituted C1-C4 alkyl, C1-C4 alkoxy-substituted C1-C4 alkoxy, —NR3R4 or fluorinated acetyl or propionyl;
- and
- R3 and R4 independently represent H, or C1-C6 alkyl;
- and
- L represents a leaving group selected from the group consisting of Cl, Br, I and trifluoromethanesulfonate.
20 more elements
A compound of the formula
- ArMetal
- wherein
- Ar represents a polysubstituted aryl group selected from the group consisting of
- wherein
- W1 represents halogen;
- X1 represents F, Cl, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy-substituted C1-C4 alkyl, C1-C4 alkoxy-substituted C1-C4 alkoxy, —CN, —NR3R4 or fluorinated acetyl or propionyl;
- Y1 represents C1-C4 alkyl, C1-C4 haloalkyl, halogen or —CN, or, when X1 and Y1 are taken together, represents —O(CH2)nO— wherein n=1 or 2;
- and
- R3 and R4 independently represent H or C1-C4 alkyl;
- wherein
- W2 represents F or Cl;
- X2 represents F, Cl, —CN, —NO2, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy-substituted C1-C4 alkyl, C1-C4 alkoxy-substituted C1-C4 alkoxy, —NR3R4 or fluorinated acetyl or propionyl;
- Y2 represents halogen, C1-C4 alkyl, C1-C4 haloalkyl or —CN, or, when W2 represents F, X2 and Y2 taken together represent —O(CH2)nO— wherein n=1 or 2;
- and
- R3 and R4 independently represent H or C1-C6 alkyl;
- and
- wherein
- Y3 represents halogen, —CN or —CF3;
- Z3 represents F, Cl, —CN, —NO2, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkylthio, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 haloalkyl, C1-C4 haloalkoxy, C1-C4 alkoxy-substituted C1-C4 alkyl, C1-C4 alkoxy-substituted C1-C4 alkoxy, —NR3R4 or fluorinated acetyl or propionyl;
- and
- R3 and R4 independently represent H, or C1-C6 alkyl;
- and
- Metal represents Mg-halide, Zn-halide, tri-(C1-C4 alkyl)tin, lithium, copper, or B(OR8)(OR9), where R8 and R9 are independent of one another, hydrogen, C1-C4 alkyl, or when taken together form an ethylene or propylene group.
20 more elements
Dependencies are inferred from the claim text.