# US 11,998,005 B2 · Herbicidal formulations comprising glyphosate and COTE-based adjuvants > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,998,005 B2 - Document ID: US11998005B2 - Status: Granted - Kind: B2 - Application number: 17/250,208 - Filed: 2019-06-13 - Published: 2021-06-24 - Granted: 2024-06-04 - Earliest claimed: 2018-06-15 - Assignees: Nouryon Chemicals International B.V. - Applicants: Nouryon Chemicals International B.V. - Inventors: Hanamanthsa Bevinakatti; Mojahedul Islam - Web page: https://patentgrep.com/patent/US11998005B2 ## CPC - A01N 25/30: characterised by the surfactants - A01N 37/38: having at least one oxygen or sulfur atom attached to an aromatic ring system - A01N 37/40: 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 - A01N 57/20: containing acyclic or cycloaliphatic radicals - C07C 217/28: having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines - C07C 233/38: having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton - A01N: PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF (preservation of food or foodstuff A23); BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES (preparations for medical, dental or toiletry purposes which kill or prevent the growth or proliferation of unwanted organisms A61K); PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS - C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS ## Abstract The present disclosure generally relates to herbicidal compositions, and more particularly, herbicidal compositions comprising glyphosate or a salt thereof and a surfactant comprising at least one castor oil triglycidyl ether-based (“COTE-based”) adjuvant. ## Claims ### Claim 1 A surfactant compound having Structure I: wherein R1 and R3 independently represent alkanol or ether-alkanol; and R2 and R4 independently represent hydrogen, alkyl, alkanol or ether-alkanol. ### Claim 2 (depends on 1) The surfactant compound according to claim 1, wherein R1 and R3 independently represent an alkanol having about 1-150 carbon atoms and about 1-150 hydroxyl groups; or an ether-alkanol having about 1-150 carbon atoms, about 1-150 hydroxyl groups, and about 1-40 ether linkages; and R2 and R4 independently represent hydrogen; an alkyl having about 1-150 carbon atoms; an alkanol having about 1-150 carbon atoms and about 1-150 hydroxyl groups; or an ether-alkanol having about 1-150 carbon atoms, about 1-150 hydroxyl groups, and about 1-40 ether linkages. ### Claim 3 (depends on 1) The surfactant compound of claim 1 having Structure I. ### Claim 4 (depends on 3) The surfactant compound according to claim 3, wherein R1 and R3 independently represent an alkanol having about 1-150 carbon atoms and about 1-150 hydroxyl groups; or an ether-alkanol having about 1-150 carbon atoms, about 1-150 hydroxyl groups, and about 1-40 ether linkages; and R2 and R4 independently represent hydrogen; an alkyl having about 1-150 carbon atoms; an alkanol having about 1-150 carbon atoms and about 1-150 hydroxyl groups; or an ether-alkanol having about 1-150 carbon atoms, about 1-150 hydroxyl groups, and about 1-40 ether linkages. ### Claim 5 A surfactant compound having Structure II: wherein R3 represents an alkanol or ether-alkanol; and R4 represents hydrogen, an alkyl, alkanol or ether-alkanol. ### Claim 6 (depends on 5) The surfactant compound according to claim 5, wherein R3 represents an alkanol having about 1-150 carbon atoms and about 1-150 hydroxyl groups; or an ether-alkanol having about 1-150 carbon atoms, about 1-150 hydroxyl groups, and about 1-40 ether linkages; and R4 represents hydrogen; an alkyl having about 1-150 carbon atoms; an alkanol having about 1-150 carbon atoms and about 1-150 hydroxyl groups; or an ether-alkanol having about 1-150 carbon atoms, about 1-150 hydroxyl groups, and about 1-40 ether linkages. ### Claim 7 A surfactant compound having Structure III: wherein R3 represents an alkanol or ether-alkanol; and R4 represents hydrogen, an alkyl, alkanol or ether-alkanol. ### Claim 8 (depends on 7) The surfactant compound according to claim 7, wherein R3 represents an alkanol having about 1-150 carbon atoms and about 1-150 hydroxyl groups; or an ether-alkanol having about 1-150 carbon atoms, about 1-150 hydroxyl groups, and about 1-40 ether linkages; and R4 represents hydrogen; an alkyl having about 1-150 carbon atoms; an alkanol having about 1-150 carbon atoms and about 1-150 hydroxyl groups; or an ether-alkanol having about 1-150 carbon atoms, about 1-150 hydroxyl groups, and about 1-40 ether linkages. ### Claim 9 (depends on 1) A surfactant composition comprising at least one surfactant of Structure I, II, or III according to claim 1. ### Claim 10 (depends on 9) The surfactant composition according to claim 9, which additionally comprises at least one co-surfactant not having Structure I, II, or III. ### Claim 11 (depends on 1) A herbicidal composition comprising glyphosate or a salt thereof and at least one surfactant of Structure I, II, or III according to claim 1. ### Claim 12 (depends on 11) The herbicidal composition according to claim 11, wherein said at least one surfactant of Structure I, II or III is/are the only surfactant(s) in the composition. ### Claim 13 (depends on 12) The herbicidal composition according claim 12, which in addition to said at least one surfactant of Structure I, II or III additionally comprises at least one co-surfactant not having Structure I, II or III. ### Claim 14 (depends on 11) The herbicidal composition according to claim 11, which in addition to said glyphosate or salt thereof further comprises at least one additional herbicidally active ingredient. ### Claim 15 (depends on 14) The composition according to claim 14, wherein the at least one additional herbicidally active ingredient is chosen from 2,4-dichlorophenoxyacetic acid (2,4-D), dicamba, glufosinate, and combinations thereof. ### Claim 16 (depends on 11) The composition according to claim 11, wherein the glyphosate salt is chosen from sodium, potassium, ammonium, isopropylamine, monoethanolamine, diethanolamine, triethanolamine, trimesium salts, and mixtures thereof. ### Claim 17 (depends on 11) The composition according to claim 11, which has a loading of glyphosate or a salt thereof of at least about 540 g a.e./L. ### Claim 18 (depends on 12) A method of controlling unwanted vegetation, said method comprising applying to said unwanted vegetation a herbicidally effective amount of a herbicidal composition according to claim 12. ### Claim 19 (depends on 1) A method of preparing a surfactant according to claim 1, said method comprising (a) reacting castor oil triglycidyl ether (COTE) with at least one primary and/or secondary amine and (b) obtaining at least one surfactant compound having the Structure I, II or III.