Herbicidal compositions including drift retardant agents and methods of making the same

Patent metadata

Field	Value
Publication number	US-11825840-B2
Application number	US-202117144774-A
Country	US
Kind code	B2
Filing date	Jan 8, 2021
Priority date	Jan 10, 2020
Publication date	Nov 28, 2023
Grant date	Nov 28, 2023

Abstract

Herbicidal compositions for reducing off-site movement or drift of herbicides are described. The herbicidal compositions can include an auxin herbicide, an oil or an ester of the oil, and a polymeric emulsifying agent, such as glycerol ethoxylate-polyricinoleate, glycerol ethoxylate-poly-(12-hydroxystearate), polyethylene glycol (PEG)-polyricinoleate, PEG-poly-(12-hydroxystearate), and a combination thereof. Methods of making such compositions and methods of making such polymeric emulsifying agents are also described.

First claim

What is claimed is:

1. A herbicidal composition concentrate comprising:
(a) at least one herbicide present in an amount (acid equivalent weight) of from about 5% by weight to about 70% by weight of the composition concentrate, wherein the at least one herbicide comprises an auxin herbicide;
(b) an oil or an ester of the oil in an amount of from about 1% by weight to about 20% by weight of the composition concentrate; and
(c) a polymeric emulsifying agent selected from the group consisting of glycerol ethoxylate-polyricinoleate, glycerol ethoxylate-poly-(12-hydroxystearate), polyethylene glycol (PEG)-polyricinoleate, PEG-poly-(12-hydroxystearate), and a combination thereof, wherein: the PEG-poly-(12-hydroxystearate) corresponds in structure to Formula D:

wherein j=50 to 250 and s+r=2 to 10, in an amount of from about 0.2% by weight to about 15% by weight of the composition concentrate.

2. The herbicidal composition concentrate of claim 1 , wherein one or more of the following are satisfied:
(i) the at least one herbicide is present in an amount (acid equivalent weight) of about 5% to about 50% by weight of the composition concentrate;
(ii) the oil or the ester of the oil is present in an amount of from about 1% by weight to about 15% by weight of the composition concentrate; and
(iii) the polymeric emulsifying agent is present in an amount of from about 0.2% by weight to about 10% by weight of the composition concentrate.

3. The herbicidal composition concentrate of claim 1 , wherein one or more of the following are satisfied:
(i) the auxin herbicide is selected from the group consisting of dicamba, an agriculturally acceptable salt of dicamba, an agriculturally acceptable ester of dicamba, 2,4-D, an agriculturally acceptable salt of 2,4-D, an agriculturally acceptable ester of 2,4-D, and a combination thereof;
(ii) the oil or the ester of the oil is a vegetable oil, an ester of the vegetable oil, or a petroleum-based oil.

4. The herbicidal composition concentrate of claim 1 , wherein one of more of the following are satisfied:
(i) the auxin herbicide is an agriculturally acceptable salt of dicamba, wherein the salt is selected from group consisting of N,N-[aminopropyl]methylamine, monoethanolamine, dimethylamine, isopropylamine, diglycolamine, a potassium salt, a sodium salt, and a combination thereof; and
(ii) the oil or the ester of the oil is selected from the group consisting soybean oil, an ester of soybean oil, canola oil, an ester of canola oil, palm oil, an ester of palm oil, rapeseed oil, an ester of rapeseed oil, sunflower seed oil, an ester of sunflower seed oil, corn oil, an ester of corn oil, peanut oil, an ester of peanut oil, sesame oil, an ester of sesame oil, olive oil, an ester of olive oil, and a combination thereof.

5. The herbicidal composition concentrate of claim 1 , wherein:
(i) the glycerol ethoxylate-polyricinoleate corresponds in structure to Formula A:

wherein i+j+k=10 to 50 and r+s+t=3 to 12;

(ii) the glycerol ethoxylate-poly-(12-hydroxystearate) corresponds in structure to Formula B:

wherein i+j+k=10 to 50 and r+s+t=3 to 12;

(iii) the polyethylene glycol (PEG)-polyricinoleate corresponds in structure to Formula C:

wherein j=50 to 250 and s+r=2 to 10; and

(iv) the PEG-poly-(12-hydroxystearate) corresponds in structure to Formula D:

wherein j=130 to 200 and s+r=3 to 6.

6. The herbicidal composition concentrate of claim 1 , further comprising one or more of:
(i) a surfactant selected from the group consisting of a phosphate ester, an alkylpolysaccharide, an alkoxylated castor oil, and a combination thereof; and
(ii) at least one monocarboxylic acid or a monocarboxylate thereof.

7. The herbicidal composition concentrate of claim 6 , wherein the at least one monocarboxylic acid or the monocarboxylate thereof is present in an amount (acid equivalent weight) of about 5% to about 30% by weight of the composition concentrate; and/or
wherein the molar ratio of the at least one monocarboxylic acid or the monocarboxylate thereof to the auxin herbicide is from about 3:10 to about 10:1.

8. The herbicidal composition concentrate of claim 6 , wherein the monocarboxylic acid is acetic acid or the monocarboxylate is potassium acetate.

9. The herbicidal composition concentrate of claim 1 , wherein the at least one herbicide further comprises an herbicide selected from the group consisting of glyphosate, an agriculturally acceptable salt of glyphosate, glufosinate, an agriculturally acceptable salt of glufosinate, and a combination thereof.

10. The herbicidal composition concentrate of claim 1 , wherein the polymeric emulsifying agent comprises a glycerol ethoxylate-polyricinoleate corresponding in structure to Formula A:

wherein i+j+k=10 to 50 and r+s+t=3 to 12.

11. The herbicidal composition concentrate of claim 1 , wherein the polymeric emulsifying agent comprises a glycerol ethoxylate-poly-(12-hydroxystearate) corresponding in structure to Formula B:

wherein i+j+k=10 to 50 and r+s+t=3 to 12.

12. The herbicidal composition concentrate of claim 1 , wherein the polymeric emulsifying agent comprises a polyethylene glycol (PEG)-polyricinoleate corresponding in structure to Formula C:

wherein j=50 to 250 and s+r=2 to 10.

13. The herbicidal composition concentrate of claim 1 , wherein the polymeric emulsifying agent comprises a PEG-poly-(12-hydroxystearate) corresponding in structure to Formula D:

wherein j=130 to 200 and s+r=3 to 6.

14. A method of making an herbicidal composition concentrate, the method comprising:
admixing at least one herbicide with an oil or an ester of the oil and a polymeric emulsifying agent to form the herbicidal composition concentrate,
wherein the at least one herbicide is admixed in an amount (acid equivalent weight) of from about 5% by weight to about 70% by weight of the composition concentrate and the at least one herbicide comprises an auxin herbicide, and the oil or ester of the oil is admixed in an amount of from about 1% by weight to about 20% by weight of the composition concentrate;
wherein the polymeric emulsifying agent is selected from the group consisting of glycerol ethoxylate-polyricinoleate, glycerol ethoxylate-poly-(12-hydroxystearate), polyethylene glycol (PEG)-polyricinoleate, PEG-poly-(12-hydroxystearate), and a combination thereof, wherein:
the PEG-poly-(12-hydroxystearate) corresponds in structure to Formula D:

wherein j=50 to 250 and s+r=2 t

Assignees

• Monsanto Technology Llc

Inventors

• Gao Jingsi
• Jimoh Ganiyu
• Macinnes Alison
• Morgenstern David

Classifications

• A01N25/24 Primary

  containing ingredients to enhance the sticking of the active ingredients · CPC title

• A01N37/36

  containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids · CPC title

• A01N37/40

  having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system · CPC title

• A01N57/20

  containing acyclic or cycloaliphatic radicals · CPC title

• A01N65/20

  Fabaceae or Leguminosae [Pea or Legume family], e.g. pea, lentil, soybean, clover, acacia, honey locust, derris or millettia · CPC title