2-substituted-6-amino-5-alkyl, alkenyl or alkynyl-4-pyrimidinecarboxylic acids and 6-substituted-4-amino-3- alkyl, alkenyl or alkynyl picolinic acids and their use as herbicides

• US 7,786,044 B2
• Filed: 10/01/2008
• Issued: 08/31/2010
• Est. Priority Date: 10/02/2007
• Status: Active Grant

• Current Assignee: Corteva Agriscience LLC (Corteva, Inc.)
• Original Assignee: Dow Agrosciences LLC (Corteva, Inc.)
• Inventors: Schmitzer, Paul R., Epp, Jeffrey B., Yerkes, Carla N., Balko, Terry W.
• Primary Examiner(s): RAO, DEEPAK R
• Application Number:
  US12/243,469
• Publication Number:
  US 20090088322A1
• Time in Patent Office: 699 Days
• Field of Search: 546/310, 504/260
• US Class Current: 504/260
• 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 47/18 containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
• CPC Class Codes: C07D 213/79 Acids; Esters
• CPC Class Codes: C07D 239/42 One nitrogen atom nitro radicals C07D239/30

Abstract

6-Amino-4-pyrimidinecarboxylic acids having alkyl, alkenyl or alkynyl substituents in the 5-position and 4-aminopicolinic acids having alkyl, alkenyl or alkynyl substituents in the 3-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 R₃ and R₄ independently represent H or C₁-C₆ alkyl.

3. A compound of claim 1 in which the agriculturally acceptable derivatives of the carboxylic acid group are agriculturally acceptable salts, esters and amides.

4. A compound of claim 1 in which R₁ is C₁-C₂ alkyl, C₁-C₂ haloalkyl, C₂-C₃ alkenyl or C₂-C₃ haloalkenyl.

5. A compound of claim 4 in which R₁ is vinyl.

6. A compound of claim 1 in which R₂ is cyclopropyl.

7. A compound of claim 1 in which R₂ is

8. A compound of claim 7 in which W₁ represents H or F, X₁ represents H, halogen, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy or —

NR₆R₇, Y₁ represents Cl or halomethyl, and Z₁ represents H or F.

10. An herbicidal composition comprising an herbicidally effective amount of a compound according to claim 1, in a mixture with an agriculturally acceptable adjuvant or carrier.

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

9. A compound having the formula