N-alkoxyamides of 6-(trisubstituted phenyl)-4-aminopicolinates and their use as selective herbicides for crops

• US 8,536,331 B2
• Filed: 02/25/2010
• Issued: 09/17/2013
• Est. Priority Date: 02/27/2009
• Status: Active Grant

• Current Assignee: Corteva Agriscience LLC (Corteva, Inc.)
• Original Assignee: Dow Agrosciences LLC (Corteva, Inc.)
• Inventors: Eckelbarger, Joseph D., Schmitzer, Paul R., Yerkes, Carla N., Boebel, Timothy A., Satchivi, Norbert M.
• Primary Examiner(s): Leeser, Erich A
• Application Number:
  US12/712,483
• Publication Number:
  US 20100222221A1
• Time in Patent Office: 1,300 Days
• Field of Search: 514/256, 514/352, 544/329, 546/309
• US Class Current: 544/329
• CPC Class Codes: A01N 43/40 six-membered rings
• CPC Class Codes: A01N 43/54 1,3-Diazines; Hydrogenated 1,3-diazines
• CPC Class Codes: A01N 43/72 having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
• CPC Class Codes: A01N 43/78 1,3-Thiazoles; Hydrogenated 1,3-thiazoles
• CPC Class Codes: A01N 43/80 five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
• CPC Class Codes: A01N 43/82 five-membered rings with three ring hetero atoms
• CPC Class Codes: C07D 213/81 Amides; Imides
• CPC Class Codes: C07D 239/28 with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
• CPC Class Codes: C07D 239/30 Halogen atoms or nitro radicals
• CPC Class Codes: C07D 239/42 One nitrogen atom nitro radicals C07D239/30
• CPC Class Codes: C07D 239/47 One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
• CPC Class Codes: C07D 405/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 413/06 linked by a carbon chain containing only aliphatic carbon atoms
• CPC Class Codes: C07D 413/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 417/12 linked by a chain containing hetero atoms as chain links

Abstract

N-Alkoxyamides of 4-aminopicolinic acids and 6-amino-4-pyrimidinecarboxylates are selective herbicides for corn, canola and sugar beet.

Claims

1. A compound of Formula I:

2. The compound of claim 1 in which X represents CH or N.

3. The compound of claim 1 in which Z represents halogen or methoxy.

4. The compound of claim 1 in which R¹ and R² represent hydrogen.

5. The compound of claim 1 in which R³ represents C₁-C₄ alkyl, C₂-C₆ alkenyl or unsubstituted or para-substituted benzyl.

6. The compound of claim 1, which is not a salt.

7. The compound of claim 1, wherein X is CH.

8. The compound of claim 1, wherein Y is phenyl substituted with 3 substituents.

9. The compound of claim 1, wherein Y is phenyl substituted with 1-4 substituents independently selected from halogen or C₁-C₃ alkoxy.

10. The compound of claim 1, wherein X represents CH or N;

Y represents substituted phenyl;

Z represents halogen or methoxy;

R¹ and R² represent hydrogen; and

R³ represents C₁-C₄ alkyl, C₂-C₆ alkenyl or unsubstituted or para-substituted benzyl.

11. The compound of claim 1, wherein the compound is

12. A compound of the following formula: