Heterocyclic red azo colorants for seed treatment applications

Patent metadata

Field	Value
Publication number	US-12286412-B2
Application number	US-202217714298-A
Country	US
Kind code	B2
Filing date	Apr 6, 2022
Priority date	Jun 10, 2021
Publication date	Apr 29, 2025
Grant date	Apr 29, 2025

Abstract

This invention relates to heterocyclic red azo colorants for seed treatment applications. The red azo colorants contain a heterocycle that includes one nitrogen atom and one sulfur atom and are free from electron-withdrawing groups on the heterocycle. Seeds for use in horticultural/agriculture applications that are coated with the heterocyclic azo colorants provide anti-counterfeiting properties to the coated seeds. A color change phenomenon is observed when the coated seeds are exposed to an acidic material, such as vinegar, and provides evidence of the authenticity of the coated seeds. The invention also relates to agricultural formulations containing the heterocyclic red azo colorants that can be used as an anti-counterfeit agents.

First claim

We claim:

1. A method for determining the authenticity of a seed or an agricultural formulation comprising the following steps:
(a) Providing a seed or an agricultural formulation that contains a red azo colorant represented by the following formula:

wherein R 1 is a heterocyclic group comprising at least one 5-membered ring incorporating one N and one S atom, and wherein the heterocyclic group is free from electron-withdrawing groups;
R 2 and R 3 are independently selected from the group consisting of H, alkyl, and poly(oxyalkylene) moieties, wherein at least one of R 2 and R 3 is a poly(oxyalkylene) moiety; and
R 4 is independently selected from the group consisting of H, alkyl, substituted alkyl, substituted nitrogen, hydroxyl, halogens and ethers;
(b) Adding an acidic material to the seed or agricultural formulation of step “a;” and
(c) Visually observing the occurrence of a color change from red to violet with the addition of the acidic material.

2. The method of claim 1 , wherein the acidic material has a pH≤3.

3. The method of claim 1 , wherein the seed of step “a” is in an aqueous solution prior to the addition of the acidic material.

4. The method of claim 1 , wherein R 1 is selected from the group consisting of thiazole, isothiazole, benzisothiazole, and benzothiazole.

5. The method of claim 4 , wherein R 1 is selected from thiazole and benzothiazole.

6. The method of claim 1 , wherein R 1 includes one or more substituents on the 5-membered ring incorporating one N and one S atom selected from the group consisting of H, alkyl, substituted alkyl, hydroxyl, substituted hydroxyl, aryl, and substituted aryl.

7. The method of claim 1 , wherein the poly(oxyalkylene) moieties are selected from ethylene oxide, propylene oxide, and butylene oxide, or combinations thereof.

8. The method of claim 1 , wherein the total number of alkylene oxide residues per colorant molecule is in the range from 4 to 250.

9. The method of claim 1 , wherein the total number of alkylene oxide residues per colorant molecule is in the range from 5 to 100.

10. The method of claim 1 , wherein the total number of alkylene oxide residues per colorant molecule is in the range from 5 to 20.

11. The method of claim 1 , wherein the red azo colorant of step “a” is present in an amount ranging from about 0.001% to about 50% by weight.

12. The method of claim 1 , wherein the red azo colorant of step “a” is present in an amount ranging from about 0.5% to about 10% by weight.

13. The method of claim 1 , wherein the red azo colorant of step “a” is represented by Formula I or Formula II:

wherein
R 2 and R 3 are independently selected from the group consisting of H, alkyl, and poly(oxyalkylene) moieties, and wherein at least one of R 2 and R 3 is a poly(oxyalkylene) moiety;
R 4 is independently selected from the group consisting of H, alkyl, substituted alkyl, substituted nitrogen, hydroxyl, halogens and ethers; and
R 5 is independently selected from the group consisting of H, alkyl, substituted alkyl, hydroxyl, substituted hydroxyl, aryl, and substituted aryl.

14. The method of claim 1 , wherein the red azo colorant of step “a” is represented by Formula III:

wherein R 2 and R 3 are independently selected from the group consisting of H, alkyl, and poly(oxyalkylene) moieties, and wherein at least one of R 2 and R 3 is a poly(oxyalkylene) moiety.

15. The method of claim 1 , wherein the red azo colorant of step “a” is represented by Formula IV:

Assignees

• Milliken & Co

Inventors

• Freund Wesley A
• Mohammad Innus

Classifications

• G01N21/78

  producing a change of colour · CPC title

• C09B29/3691

  containing nitrogen and sulfur as heteroatom · CPC title

• C09B29/0813

  substituted by OH, O-C(=X)-R, O-C(=X)-X-R, O-R (X being O,S,NR; R being hydrocarbonyl) · CPC title

• C09B29/0088

  Benzothiazoles · CPC title

• C09B29/0085

  Thiazoles or condensed thiazoles · CPC title