Herbicidal pyrimidines

• US 9,144,240 B2
• Filed: 08/08/2014
• Issued: 09/29/2015
• Est. Priority Date: 12/19/2003
• Status: Active Grant

• Current Assignee: Corteva Agriscience LLC (Corteva, Inc.)
• Original Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.)
• Inventors: Clark, David Alan, Finkelstein, Bruce Lawrence, Armel, Gregory Russell, Wittenbach, Vernon Arie
• Primary Examiner(s): RAO, DEEPAK R
• Application Number:
  US14/455,251
• Publication Number:
  US 20140350251A1
• Time in Patent Office: 417 Days
• Field of Search: 544/329, 504/225, 504/239, 504/242
• US Class Current: 1/1
• CPC Class Codes: A01N 2300/00 Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
• CPC Class Codes: A01N 43/54 1,3-Diazines; Hydrogenated 1,3-diazines
• CPC Class Codes: A01N 47/34 containing the groups , e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
• CPC Class Codes: A01N 47/36 containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
• 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 239/48 Two nitrogen atoms
• CPC Class Codes: C07D 401/12 linked by a chain containing hetero atoms as chain links
• CPC Class Codes: C07D 405/04 directly linked by a ring-member-to-ring-member bond
• CPC Class Codes: C07D 405/12 linked by a chain containing hetero atoms as chain links

Abstract

Compounds of Formula I, and their N-oxides and agriculturally suitable salts, are disclosed which are useful for controlling undesired vegetation

wherein

• • R¹ is cyclopropyl optionally substituted with 1-5 R⁵, isopropyl optionally substituted with 1-5 R⁶, or phenyl optionally substituted with 1-3 R⁷;
  • R² is ((O)_jC(R¹⁵)(R¹⁶))_kR;
  • R is CO₂H or a herbicidally effective derivative of CO₂H;
  • R³ is halogen, cyano, nitro, OR²⁰, SR²¹ or N(R²²)R²³;
  • R⁴ is —N(R²⁴)R²⁵ or —NO₂;
  • j is 0 or 1; and k is 0 or 1; provided that when k is 0, then j is 0;
  • and R⁵, R⁶, R⁷, R¹⁵, R¹⁶, R²⁰, R²¹, R²², R²³, R²⁴ and R²⁵ are as defined in the disclosure.

Also disclosed are compositions comprising the compounds of Formula I and a method for controlling undesired vegetation which involves contacting the vegetation or its environment with an effective amount of a compound of Formula I. Also disclosed are compositions comprising a compound of Formula I and at least one additional active ingredient selected from the group consisting of an other herbicide and a herbicide safener.

Claims

1. A compound that is 6-amino-5-chloro-2-cyclopropyl-4-pyrimidinecarboxylic acid monopotassium salt.

2. A herbicidal mixture comprising a herbicidally effective amount of a compound of claim 1 and an effective amount of at least one additional active ingredient selected from the group consisting of an other herbicide and a herbicide safener.

3. A method for controlling the growth of undesired vegetation comprising contacting the vegetation or its environment with a herbicidally effective amount of a compound of claim 1.