Heterocycle-containing amino acid compound and use thereof

• US 10,638,758 B2
• Filed: 11/01/2016
• Issued: 05/05/2020
• Est. Priority Date: 11/09/2015
• Status: Active Grant

• Current Assignee: Tokushima University, Aichi Steel Corporation (Toyota Motor Corporation)
• Original Assignee: Aichi Steel Corporation (Toyota Motor Corporation)
• Inventors: Namba, Kosuke, Murata, Yoshiko
• Primary Examiner(s): Pryor, Alton N
• Application Number:
  US15/767,660
• Publication Number:
  US 20180303093A1
• Time in Patent Office: 1,281 Days
• Field of Search: None
• CPC Class Codes: A01N 43/36 five-membered rings
• CPC Class Codes: A01N 59/16 Heavy metals; Compounds thereof
• CPC Class Codes: C05D 9/02 containing trace elements
• CPC Class Codes: C05F 11/10 Fertilisers containing plant vitamins or hormones
• CPC Class Codes: C07D 207/16 Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
• CPC Class Codes: Y02P 20/55 Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Abstract

Provided is a novel heterocycle-containing amino acid compound that has a metal uptake ability equivalent to mugineic acids and can be less expensively produced than mugineic acids. Also provided are a fertilizer and a plant growth regulating agent each comprising the novel heterocycle-containing amino acid compound. The present invention is a heterocycle-containing amino acid compound represented by general formula (1):

(wherein: R¹, R² and R³ are the same or different and represent a hydrogen atom or a carboxyl-protecting group; R⁴ represents a hydrogen atom or a hydroxy-protecting group; R⁵ represents a hydrogen atom or an amino-protecting group; and n is an integer of 1-3) or a salt thereof and use of the same.

Claims

1. A heterocycle-containing amino acid compound represented by the following formula (1):

2. The compound or salt thereof according to claim 1, wherein the heterocycle-containing amino acid compound represented by the formula (1) is a compound represented by the following formula (1A):

3. The compound or salt thereof according to claim 1, wherein R¹, R², R³, R⁴ and R⁵ are each a hydrogen atom.

4. The compound or salt thereof according to claim 1, wherein n is 1.

5. A complex comprising the compound or salt thereof according to claim 1 and a metal.

6. The complex according to claim 5, wherein the metal is iron.

7. A mixture comprising the compound or salt thereof according to claim 1 and a metal compound.

8. The mixture according to claim 7, wherein the metal compound is an iron compound.

9. A fertilizer or a plant growth regulating agent, comprising the mixture according to claim 7.

10. A fertilizer comprising the compound or salt thereof according to claim 1.

11. A plant growth regulating agent comprising the compound or salt thereof according to claim 1.