N-(substituted)-5-fluoro-4-imino-3-methyl-2-oxo-3,4-dihydropyrimidine-1(2H)-carboxylate derivatives

• US 9,908,855 B2
• Filed: 04/05/2017
• Issued: 03/06/2018
• Est. Priority Date: 12/28/2012
• Status: Active Grant

• Current Assignee: Adama Makhteshim Limited (ADAMA Ltd.)
• Original Assignee: Adama Makhteshim Limited (ADAMA Ltd.)
• Inventors: Lorsbach, Beth, Owen, W. John, Stelzer, Lindsey, Yao, Chenglin
• Primary Examiner(s): Pagano, Alexander R
• Assistant Examiner(s): Sackey, Ebenezer O
• Application Number:
  US15/480,040
• Publication Number:
  US 20170204069A1
• Time in Patent Office: 335 Days
• CPC Class Codes: A01N 43/54 1,3-Diazines; Hydrogenated 1,3-diazines
• CPC Class Codes: A01N 47/22 O-Aryl or S-Aryl esters thereof
• CPC Class Codes: C07D 239/47 One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine

Abstract

This present disclosure is related to the field of N-(substituted)-5-fluoro-4-imino-3-methyl-2-oxo-3,4-di-hydropyrimidine-1(2H)-carboxylates and their derivatives and to the use of these compounds as fungicides. Also provided are methods of controlling a fungal disease such as Septoria tritici, comprising administering an effective amount of the fungicide compound to at lease one surface associated with the plant, seed or soil.

Claims

1. A compound of Formula II:

2. The compound of claim 1, wherein R⁶ is C₁-C₆ alkyl.

3. The compound of claim 1, wherein R⁶ is methyl.

4. A process of preparing a compound of Formula I:

5. The process of claim 4, wherein R² and R⁶ are CH₃, R³ is H, and R⁵ and R⁷ are methoxy.

6. The process of claim 4, wherein R² and R⁶ are CH₃, R³ is —

C(═

O)OR⁴, and R⁵ and R⁷ methoxy.

7. The process of claim 4, wherein R² and R⁶ are CH₃, R³ is H, and R⁵ and R⁷ are methyl.

8. The process of claim 4, wherein R² and R⁶ are CH₃, R³ is H, and R⁵ and R⁷ are H.

9. The process of claim 4, wherein the contacting step is carried out at a temperature of 70°

C.