# US 9,750,251 B2 · Liquid herbicidal preparations > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 9,750,251 B2 - Document ID: US9750251B2 - Status: Granted - Kind: B2 - Application number: 12/867,618 - Filed: 2009-02-05 - Published: 2010-12-30 - Granted: 2017-09-05 - Earliest claimed: 2008-02-14 - Assignees: Bayer Intellectual Property GmbH - Applicants: Gerhard Johann; Udo Bickers; Mandy Denner; Rainer Buckpesch; Frank Sixl - Inventors: Gerhard Johann; Udo Bickers; Mandy Denner; Rainer Buckpesch; Frank Sixl - Web page: https://patentgrep.com/patent/US9750251B2 ## CPC - A01N 43/54: 1,3-Diazines; Hydrogenated 1,3-diazines - A01N 25/02: containing liquids as carriers, diluents or solvents - A01N 25/04: Dispersions, {emulsions, suspoemulsions, suspension concentrates} or gels (foams A01N25/16) - A01N 25/30: characterised by the surfactants - A01N 43/12: condensed with a carbocyclic ring - A01N 47/22: O-Aryl or S-Aryl esters thereof - 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 ## Abstract Herbicidal oil dispersions comprising (a) desmedipham and/or phenmedipham, ethofumesate and lenacil, (b) one or more surfactants, c) one or more compounds which as far as possible are polar but at the same time are water-insoluble or have a solubility in water of up to 5 g/l, from the group of fully esterified organic phosphates and fully esterified phosphonates, as solvents, d) optionally further organic solvents, e) optionally further, customary formulating auxiliaries, f) optionally water are stable formulations and are suitable for controlling weeds, particularly for selective control in beet crops. ## Claims ### Claim 1 An oil dispersion comprising: (a) a herbicidally effective amount of a plurality of compounds comprising: desmedipham of the formula (a1): phenmedipham of the formula (a2): ethofumesate of the formula (a3): and lenacil of the formula (a4): (b) one or more surfactants; (c) one or more compounds, selected from the group consisting of fully esterified organic phosphates and fully esterified phosphonates, as solvents; (d) if desired, other organic solvents; (e) if desired, other, customary formulating auxiliaries; and (f) if desired, water wherein the amounts of components (a) to (f) are: (a) 15% to 30% by weight of active ingredients (a1) to (a4), (b) 15% to 60% by weight of surfactants, (c) 15% to 50% by weight of phosphoric triesters or phosphonic diesters, (d) 0% to 20% by weight of further solvents, (e) 0% to 10% by weight of further, customary formulating auxiliaries, (f) 0% to 10% by weight of water, wherein the weight ratio of active ingredients (a1):(a2):(a3):(a4) is in a range of from (1):(1):(1):(0.3) to (1):(5):(8):(4). ### Claim 2 (depends on 1) The oil dispersion as claimed in claim 1 wherein the one or more surfactants (b) is (b1) a carbocyclic aromatics based surfactant, (b2) a non-aromatic based surfactant that contains no carbocyclic aromatic moieties, or a mixture of (b1) and (b2). ### Claim 3 (depends on 1) The oil dispersion as claimed in claim 1; wherein the one or more surfactants (b) is (b1) a carbocyclic aromatics based surfactant selected from the group consisting of: (b 1.1) phenols, phenyl (CcC4)alkyl ethers or (poly)alkoxylated phenols; (b 1.2) (poly)alkylphenols or (poly)alkylphenol alkoxylates; (b 1.3) polyarylphenols or polyarylphenol alkoxylates; (b 1.4) compounds which formally represent the reaction products of the molecules described under (b1.1) to (b1.3) with sulfuric acid or phosphoric acid, and their salts neutralized with suitable bases; and (b1.5) acidic (poly)alkyl- and (poly)aryl-benzenesulfonates and such neutralized with suitable bases. ### Claim 4 (depends on 1) The oil dispersion as claimed in claim 1; wherein the one or more surfactants (b) is (b1) a carbocyclic aromatics based surfactant selected from the group consisting of: phenol reacted with 4 to 10 mol of ethylene oxide; triisobutylphenol, tri(sec-butyl)phenol or tri(n-butyl)phenol reacted with 4 to 50 mol of ethylene oxide; nonylphenol reacted with 4 to 50 mol of ethylene oxide; tristyrylphenol reacted with 4 to 150 mol of ethylene oxide; and acidic (linear) dodecylbenzenesulfonate. ### Claim 5 (depends on 1) The oil dispersion as claimed in claim 1; wherein component (c) comprises one or more compounds selected from the group consisting of (c1) and (c2): (c1) water-insoluble polar esters of phosphoric acid from the group consisting of: (c1.1) phosphoric triesters with monohydric alkanols having 5 to 22 carbon atoms; (c1.2) phosphoric triesters with dials or polyols; (c1.3) phosphoric triesters with aryl, alkylaryl, poly(alkyl)aryl and poly(arylalkyl)aryl alcohols; (c1.4) phosphoric triesters with alkoxylated alcohols obtained by reacting the alcohol components specified above under (c1.1) to (c1.3) with alkylene oxides; (c1.5) phosphoric triesters with alkoxylated alcohols obtained by reacting monohydric alkanols having 1 to 4 carbon atoms and alkylene oxides; and (c1.6) phosphoric triesters with a mixture of alcohols comprising two or more of the alcohol components specified above under groups (c1.1) to (c1.5); where the 3 alcohol components of the phosphoric ester from groups (c1.1) to (c1.5) may in each case be identical or different and are selected such that the ester can be used as a water-insoluble polar solvent; and (c2) water-insoluble and at the same time polar phosphonates based on alkyl-, aryl-, alkylaryl-, poly(alkyl)-aryl-, or poly(arylalkyl)-aryl-phosphonic acids doubly esterified with alcohols and/or with alkoxylated alcohols, selected from the following group: (c2.1) diesters of phosphonic acids with monohydric alkanols having 1 to 22 carbon atoms; (c2.2) diesters of phosphonic acids with diols or polyols; (c2.3) diesters of phosphonic acids with aryl, alkylaryl, poly(alkyl)aryl or poly(arylalkyl)aryl alcohols; (c2.4) diesters of phosphonic acids with alkoxylated alcohols which are obtained by reacting the alcohols specified above under (c2.1) to (c2.3) with alkylene oxides; and (c2.5) diesters of phosphonic acids with a mixture of alcohols from two or more of the alcohol components specified above under groups (c2.1) to (c2.4); where the 2 alcohol components of the phosphonic diester from groups (c2.1) to (c2.4) may in each case be identical or different and are selected such that the ester can be used as a largely water-insoluble polar solvent. ### Claim 6 (depends on 1) The oil dispersion as claimed in claim 1; wherein component (c) is selected from the group consisting of: (c1.7) phosphoric triesters with alkoxylated short-chain alcohols having 1 to 22 carbon atoms in the alkyl radical and 1 to 30 alkyleneoxy units in the polyalkyleneoxy moiety; (c1.8) phosphoric triesters with alkyl alcohols having 5 to 22 carbon atoms; and (c1.9) phosphoric triesters based on ortho-phosphoric acid esterified partially with optionally alkoxylated alcohols having 1 to 22 carbon atoms in the alkyl radical or with optionally alkoxylated phenol derivatives, in each case having 0 to 30 alkyleneoxy units in the polyalkyleneoxy moiety, the remaining OH valences of the ortho-phosphoric acid having been subsequently alkoxylated. ### Claim 7 (depends on 1) The oil dispersion as claimed in claim 1; wherein component (c) is tributoxyethyl phosphate. ### Claim 8 (depends on 1) The oil dispersion as claimed in claim 1, wherein the combination of compounds (a1), (a2), (a3), and (a4) has a synergistic effect that gives a greater herbicidal activity than if the compound (a4) is applied separately from the herbicides (a1), (a2), and (a3). ### Claim 9 (depends on 1) A method of controlling unwanted plant growth, comprising: applying an effective amount of the oil dispersion as claimed in claim 1, optionally following dilution with water, to the plants, plant parts or cultivation area. ### Claim 10 (depends on 1) A process for preparing the oil dispersion as defined in claim 1, comprising: mixing the components (a) to (f) with one another. ### Claim 11 (depends on 10) The method as claimed in claim 10; wherein weed plants are controlled selectively in beet crops.