# US 5,703,016 A · Surfactant composition for use with glyphosate comprising dimethyl amine oxide, polyethoxylated alcohol, and pyridinium halide > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 5,703,016 A - Document ID: US5703016A - Status: Granted - Kind: A - Application number: 08/720,519 - Filed: 1996-09-30 - Granted: 1997-12-30 - Earliest claimed: 1996-09-30 - Assignees: Albemarle Corporation - Inventors: Ralph W. Magin; Joe D. Sauer - Web page: https://patentgrep.com/patent/US5703016A ## CPC - A01N 25/30: characterised by the surfactants - A01N 57/20: containing acyclic or cycloaliphatic radicals - Y10S 516/07: Organic amine, amide, or n-base containing - 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 - Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS ## Abstract Glyphosate formulations which are effective even when employed at dosages below the dosage currently recommended for post-emergent herbicidal or plant growth regulant use are described. They are formulated as water solutions or powders or granules from (a) one or more agriculturally acceptable salts of glyphosate; (b) at least one water-soluble long chain aliphatic hydrocarbyl dimethyl amine oxide in which the hydrocarbyl group is a linear or substantially linear saturated or olefinically unsaturated aliphatic group having in the range of about 8 to about 22 carbon atoms; (c) at least one water-soluble straight or branched chain saturated or olefinically unsaturated alcohol ethoxylate having in the range of about 8 to about 24 carbon atoms in the aliphatic hydrocarbyl group and in the range of about 2 to about 50 ethyleneoxy groups per molecule, and (d) at least one water-soluble or water-dispersible N-hydrocarbyl pyridinium halide having up to about 24 carbon atoms in the molecule, and wherein (i) the hydrocarbyl group attached to the nitrogen atom of the heterocyclic aromatic ring of the pyridinium nucleus is a saturated or olefinically unsaturated aliphatic hydrocarbyl group having in the range of about 4 to about 18 carbon atoms, and (ii) the ring carbon atoms of the pyridinium nucleus itself are either unsubstituted or one or more of such ring carbon atoms are substituted with a short chain alkyl group of up to about 4 carbon atoms, or a solution or suspension thereof. ## Claims ### Claim 1 A composition which comprises a solution or suspension containing at least a herbicidal or plant growth regulating amount of a composition formed by mixing the following ingredients with water concurrently and/or in any sequence and/or in any preformed combination and/or subcombination thereof: a) at least one agriculturally acceptable salt of glyphosate, or a solution or suspension thereof; b) at least one water-soluble or water-dispersible long chain aliphatic hydrocarbyl dimethyl amine oxide in which the hydrocarbyl group is a linear or substantially linear saturated or olefinically unsaturated aliphatic group having in the range of about 8 to about 22, carbon atoms, or a solution or suspension thereof; c) at least one water-soluble or water-dispersible polyethoxylated monohydric saturated or olefinically-unsaturated alcohol of the formula: RO--›CH.sub.2 CH.sub.2 O!.sub.n H in which R has at least about 8 carbon atoms and is a straight or branched chain saturated aliphatic hydrocarbyl group or a straight or branched chain monoolefinically or a poly-olefinically unsaturated hydrocarbyl group having from 1 to 3 olefinic double bonds, and in which n is in the range of about 2 to about 50, or a solution or suspension thereof; and d) at least one water-soluble or water-dispersible N-hydrocarbyl pyridinium halide having up to about 24 carbon atoms in the molecule, and wherein (i) the hydrocarbyl group attached to the nitrogen atom of the heterocyclic aromatic ring of the pyridinium nucleus is a saturated or olefinically unsaturated aliphatic hydrocarbyl group having in the range of about 4 to about 18 carbon atoms, and (ii) the ring carbon atoms of the pyridinium nucleus itself are either unsubstituted or one or more of such ring carbon atoms are substituted with a short chain alkyl group of up to about 4 carbon atoms, or a solution or suspension thereof. ### Claim 2 (depends on 1) A composition according to claim 1 wherein said ingredient a) before it is mixed with any other ingredient used in forming said composition is an amine or alkylsulfonium salt of glyphosate or a solution or suspension thereof. ### Claim 3 (depends on 1) A composition according to claim 1 wherein said ingredient a) before it is mixed with any other ingredient used in forming said composition is the isopropyl amine salt of glyphosate or a solution or suspension thereof. ### Claim 4 (depends on 1) A composition according to claim 1 wherein said ingredient a) is the only herbicide used in forming said composition. ### Claim 5 (depends on 1) A composition according to claim 1 wherein said ingredient b) before it is mixed with any other ingredient used in forming said composition is one or more alkyl dimethyl amine oxides in which the alkyl group contains about 8 to about 16 carbon atoms, or a solution or suspension thereof; wherein said ingredient c) before it is mixed with any other ingredient used in forming said composition is one or more polyethoxylated saturated straight chain aliphatic alcohols in which the hydrocarbyl group has in the range of about 10 to about 20 carbon atoms, and in which there is an average in the range of about 5 to about 20 ethyleneoxy groups in the molecule, or a solution or suspension thereof; and wherein said ingredient d) before it is mixed with any other ingredient used in forming said composition is one or more N-alkyl pyridinium chlorides or bromides in which the N-alkyl group has in the range of about 10 to about 18 carbon atoms and in which the ring carbon atoms of the pyridinium nucleus itself are unsubstituted, or a solution or suspension thereof. ### Claim 6 (depends on 1) A composition according to claim 1 wherein said ingredient a) before it is mixed with any other ingredient used in forming said composition is one or more amine or alkylsulfonium salts of glyphosate, or a solution or suspension thereof; wherein said ingredient b) before it is mixed with the water or with any other ingredient used in forming said composition is one or more alkyl dimethyl amine oxides in which the alkyl group contains in the range of about 12 to about 16 carbon atoms, or a solution or suspension thereof; wherein said ingredient c) before it is mixed with the water or with any other ingredient used in forming said composition is a mixture of lauryl and myristyl alcohol ethoxylates having an average in the range of about 6 to about 12 ethyleneoxy groups per molecule, or a solution or suspension thereof; and wherein said ingredient d) before it is mixed with the water or with any other ingredient used in forming said composition is one or more N-alkyl pyridinium chlorides or bromides in which the alkyl group is an n-alkyl group having in the range of about 10 to about 16 carbon atoms, or a solution or suspension thereof. ### Claim 7 (depends on 6) A composition according to claim 6 wherein said ingredient a) before it is mixed with the water or with any other ingredient used in forming said composition is the isopropyl amine salt of glyphosate, or a solution or suspension thereof. ### Claim 8 (depends on 1) A composition according to claim 1 wherein the solution contains only the elements C, H, O, N, P; and Cl or Br, and optionally S, and is formed using deionized water. ### Claim 9 (depends on 1) A composition according to claim 1 wherein said ingredient a) before it is mixed with water or any other ingredient used in forming said composition is an amine salt of glyphosate; wherein on an active ingredient basis the weight ratio of ingredients b), c) and d) used in forming said solution is such that for each part by weight of d) there are in the range of about 0.3 to about 3 parts by weight of b), and in the range of about 0.3 to about 3 parts by weight of c); and wherein said solution is an aqueous concentrate adapted for dilution with water before use. ### Claim 10 (depends on 1) A composition according to claim 1 wherein said ingredient a) before it is mixed with water or any other ingredient used in forming said composition is an amine salt of glyphosate; wherein on an active ingredient basis the weight ratio of ingredients b), c) and d) used in forming said solution is such that for each part by weight of d) there are in the range of about 0.3 to about 3 parts by weight of b), and in the range of about 0.3 to about 3 parts by weight of c); and wherein said solution is a dilute water solution adapted for direct application to at least one plant species. ### Claim 11 (depends on 1) A composition according to claim 1 wherein ingredient b) is tetradecyldimethylamine oxide, ingredient e) is a mixture of ethoxylated lauryl, myristic and cetyl alcohols with an average of about 9 ethylene oxide units per molecule, and ingredient d) is N-dodecylpyridinium bromide. ### Claim 12 A composition which comprises a powder or granular mixture containing at least a herbicidally or plant growth regulating amount of a composition formed from a combination of the following ingredients brought together concurrently and/or in any sequence and/or in any preformed combination and/or subcombination thereof: a) at least one agriculturally acceptable salt of glyphosate, or a solution or suspension thereof; b) at least one water-soluble or water-dispersible long chain aliphatic hydrocarbyl dimethyl amine oxide in which the hydrocarbyl group is a linear or substantially linear saturated or olefinically unsaturated aliphatic group having in the range of about 8 to about 22 carbon atoms, or a solution or suspension thereof; c) at least one water-soluble or water-dispersible polyethoxylated monohydric saturated or olefinically-unsaturated alcohol of the formula: RO--›CH.sub.2 CH.sub.2 O!.sub.n H in which R has at least about 8 carbon atoms and is a straight or branched chain saturated aliphatic hydrocarbyl group or a straight or branched chain monoolefinically or a poly-olefinically unsaturated hydrocarbyl group having from 1 to 3 olefinic double bonds, and in which n is in the range of about 2 to about 50, or a solution or suspension thereof; and d) at least one water-soluble or water-dispersible N-hydrocarbyl pyridinium halide having up to about 24 carbon atoms in the molecule, and wherein (i) the hydrocarbyl group attached to the nitrogen atom of the heterocyclic aromatic ring of the pyridinium nucleus is a saturated or olefinically unsaturated aliphatic hydrocarbyl group having in the range of about 4 to about 18 carbon atoms, and (ii) the ring carbon atoms of the pyridinium nucleus itself are either unsubstituted or one or more of such ring carbon atoms are substituted with a short chain alkyl group of up to about 4 carbon atoms, or a solution or suspension thereof. ### Claim 13 (depends on 12) A composition according to claim 12 wherein said ingredient a) before it is mixed with any other ingredient used in forming said composition is an amine or alkylsulfonium salt of glyphosate or a solution or suspension thereof. ### Claim 14 (depends on 12) A composition according to claim 12 wherein said ingredient a) before it is mixed with any other ingredient used in forming said composition is the isopropyl amine salt of glyphosate or a solution or suspension thereof. ### Claim 15 (depends on 12) A composition according to claim 12 wherein said ingredient a) is the only herbicide used in forming said composition. ### Claim 16 (depends on 12) A composition according to claim 12 wherein said ingredient b) before it is mixed with any other ingredient used in forming said composition is one or more alkyl dimethyl amine oxides in which the alkyl group contains about 8 to about 16 carbon atoms, or a solution or suspension thereof; wherein said ingredient c) before it is mixed with any other ingredient used in forming said composition is one or more polyethoxylated saturated straight chain aliphatic alcohols in which the hydrocarbyl group has in the range of about 10 to about 20 carbon atoms, and in which there is an average in the range of about 5 to about 20 ethyleneoxy groups in the molecule, or a solution or suspension thereof; and wherein said ingredient d) before it is mixed with any other ingredient used in forming said composition is one or more N-alkyl pyridinium chlorides or bromides in which the N-alkyl group has in the range of about 10 to about 18 carbon atoms and in which the ring carbon atoms of the pyridinium nucleus itself are unsubstituted, or a solution or suspension thereof. ### Claim 17 (depends on 12) A composition according to claim 12 wherein said ingredient a) before it is mixed with any other ingredient used in forming said composition is one or more amine or alkylsulfonium salts of glyphosate, or a solution or suspension thereof; wherein said ingredient b) before it is mixed with any other ingredient used in forming said composition is one or more alkyl dimethyl amine oxides in which the alkyl group contains in the range of about 12 to about 16 carbon atoms, or a solution or suspension thereof; wherein said ingredient c) before it is mixed with any other ingredient used in forming said composition is a mixture of lauryl and myristyl alcohol ethoxylates having an average in the range of about 6 to about 12 ethyleneoxy groups per molecule, or a solution or suspension thereof; and wherein said ingredient d) before it is mixed with any other ingredient used in forming said composition is one or more N-alkyl pyridinium chlorides or bromides in which the alkyl group is an n-alkyl group having in the range of about 10 to about 16 carbon atoms, or a solution or suspension thereof. ### Claim 18 (depends on 17) A composition according to claim 17 wherein said ingredient a) before it is mixed with any other ingredient used in forming said composition is the isopropyl amine salt of glyphosate, or a solution or suspension thereof. ### Claim 19 (depends on 12) A composition according to claim 12 wherein the composition contains only the elements C, H, O, N, P, and Cl or Br, and optionally S. ### Claim 20 (depends on 12) A composition according to claim 12 wherein ingredient b) is tetradecyldimethylamine oxide, ingredient c) is a mixture of ethoxylated lauryl, myristic and cetyl alcohols with an average of about 9 ethylene oxide units per molecule, and ingredient d) is N-dodecylpyridinium bromide. ### Claim 21 A surfactant composition which comprises a composition formed from the following active ingredients: 1) at least one water-soluble or water-dispersible long chain aliphatic hydrocarbyl dimethyl amine oxide in which the hydrocarbyl group is a linear or substantially linear saturated or olefinically unsaturated aliphatic group having in the range of about 8 to about 22 carbon atoms, or a solution or suspension thereof; 2) at least one water-soluble or water-dispersible polyethoxylated monohydric saturated or olefinically-unsaturated alcohol of the formula: RO--›CH.sub.2 CH.sub.2 O!.sub.n H in which R has at least about 8 carbon atoms and is a straight or branched chain saturated aliphatic hydrocarbyl group or a straight or branched chain monoolefinically or a poly-olefinically unsaturated hydrocarbyl group having from 1 to 3 olefinic double bonds, and in which n is in the range of about 2 to about 50, or a solution or suspension thereof; and 3) at least one water-soluble or water-dispersible N-hydrocarbyl pyridinium halide having up to about 24 carbon atoms in the molecule, and wherein (i) the hydrocarbyl group attached to the nitrogen atom of the heterocyclic aromatic ring of the pyridinium nucleus is a saturated or olefinically unsaturated aliphatic hydrocarbyl group having in the range of about 4 to about 18 carbon atoms, and (ii) the ring carbon atoms of the pyridinium nucleus itself are either unsubstituted or one or more of such ring carbon atoms are substituted with a short chain alkyl group of up to about 4 carbon atoms, or a solution or suspension thereof; and wherein on an active ingredient basis the weight ratio of ingredients 1), 2) and 3) used in forming said composition is such that for each part by weight of 3) there are in the range of about 0.3 to about 3 parts by weight of 1), and in the range of about 0.3 to about 3 parts by weight of 2). ### Claim 22 (depends on 21) A composition according to claim 21 wherein ingredient 1) is tetradecyldimethylamine oxide, ingredient 2) is a mixture of ethoxylated lauryl, myristic and cetyl alcohols with an average of about 9 ethylene oxide units per molecule, and ingredient 3) is N-dodecylpyridinium bromide. ### Claim 23 A method of controlling vegetation Which comprises applying to plant foliage a herbicidal or growth regulant amount of a composition formed by mixing the following ingredients with water concurrently and/or in any sequence and/or in any preformed combination and/or subcombination thereof: a) at least one agriculturally acceptable salt of glyphosate, or a solution or suspension thereof; b) at least one water-soluble or water-dispersible long chain aliphatic hydrocarbyl dimethyl amine oxide in which the hydrocarbyl group is a linear or substantially linear saturated or olefinically unsaturated aliphatic group having in the range of about 8 to about 22 carbon atoms, or a solution or suspension thereof; c) at least one water-soluble or water-dispersible polyethoxylated monohydric saturated or olefinically-unsaturated alcohol of the formula: RO--›CH.sub.2 CH.sub.2 O!.sub.n H in which R has at least about 8 carbon atoms and is a straight or branched chain saturated aliphatic hydrocarbyl group or a straight or branched chain monoolefinically or a poly-olefinically unsaturated hydrocarbyl group having from 1 to 3 olefinic double bonds, and in which n is in the range of about 2 to about 50, or a solution or suspension thereof; and d) at least one water-soluble or water-dispersible N-hydrocarbyl pyridinium halide having up to about 24 carbon atoms in the molecule, and wherein (i) the hydrocarbyl group attached to the nitrogen atom of the heterocyclic aromatic ring of the pyridinium nucleus is a saturated or olefinically unsaturated aliphatic hydrocarbyl group having the range of about 4 to about 18 carbon atoms, and (ii) the ring carbon atoms of the pyridinium nucleus itself are either unsubstituted or one or more of such ring carbon atoms are substituted with a short chain alkyl group of up to about 4 carbon atoms, or a solution or suspension thereof. ### Claim 24 (depends on 23) A method according to claim 23 wherein said ingredient a) before it is mixed with the water or with any other ingredient used in forming said composition is an amine or alkylsulfonium salt of glyphosate or a solution or suspension thereof. ### Claim 25 (depends on 23) A method according to claim 23 wherein said ingredient a) before it is mixed with the water or with any other ingredient used in forming said composition is the isopropyl amine salt of glyphosate or a solution or suspension thereof. ### Claim 26 (depends on 23) A method according to claim 23 wherein ingredient a) is the only herbicide used in forming said composition. ### Claim 27 (depends on 23) A method according to claim 23 wherein said ingredient b) before it is mixed with the water or with any other ingredient used in forming said composition is one or more alkyl dimethyl amine oxides in which the alkyl group contains about 8 to about 16 carbon atoms, or a solution of suspension thereof; wherein said ingredient c) before it is mixed with the water or with any other ingredient used in forming said composition is one or more polyethoxylated saturated straight chain aliphatic alcohols in which the hydrocarbyl group has in the range of about 10 to about 20 carbon atoms, and in which there is an average in the range of about 5 to about 20 ethyleneoxy groups in the molecule, or a solution or suspension thereof; and wherein said, ingredient d) before it is mixed with the water or with any other ingredient used in forming said composition is one or more N-alkyl pyridinium chlorides or bromides in which the N-alkyl group his in the range of about 10 to about 18 carbon atoms and in which the ring carbon atoms of the pyridinium nucleus itself are unsubstituted, or a solution or suspension thereof. ### Claim 28 (depends on 23) A method according to claim 23 wherein said ingredient a) before it is mixed with the water or with any other ingredient used in forming said composition is one or more amine or alkylsulfonium salts of glyphosate, or a solution or suspension thereof; wherein said ingredient b) before it is mixed with the water or with any other ingredient used in forming said composition is one or more alkyl dimethyl amine oxides in which the alkyl group contains in the range of about 12 to about 16 carbon atoms, or a solution or suspension thereof; wherein said ingredient c) before it is mixed with the water or with any other ingredient used in forming said composition is a mixture of lauryl and myristyl alcohol ethoxylates having an average in the range of about 6 to about 12 ethyleneoxy groups per molecule, or a solution or suspension thereof; and wherein said ingredient d) before it is mixed with the water or with any other ingredient used in forming said composition is one or more N-alkyl pyridinium chlorides or bromides in which the alkyl group is an n-alkyl group having in the range of about 10 to about 16 carbon atoms, or a solution or suspension thereof. ### Claim 29 (depends on 28) A method according to claim 28 wherein said ingredient a) before it is mixed with the water or with any other ingredient used in forming said composition is the isopropyl amine salt of glyphosate, or a solution or suspension thereof. ### Claim 30 (depends on 23) A method according to claim 23 wherein ingredient b) is tetradecyldimethylamine oxide, ingredient c) is a mixture of ethoxylated lauryl, myristic and cetyl alcohols with an average of about 9 ethylene oxide units per molecule, and ingredient d) is N-dodecylpyridinium bromide. ### Claim 31 A method of controlling vegetation which comprises applying to plant foliage a herbicidal or plant growth regulant amount of a herbicide or plant growth regulant composition containing only the elements C, H, O, N, P, and Cl or Br, and optionally S, and formed from the following ingredients: a) at least one agriculturally acceptable salt of glyphosate, or a solution or suspension thereof; b) at least one water-soluble or water-dispersible long chain aliphatic hydrocarbyl dimethyl amine oxide in which the hydrocarbyl group is a linear or substantially linear saturated or olefinically unsaturated aliphatic group having in the range of about 8 to about 22 carbon atoms, or a solution or suspension thereof; c) at least one water-soluble or water-dispersible polyethoxylated monohydric saturated or olefinically-unsaturated alcohol of the formula: RO--›CH.sub.2 CH.sub.2 O!.sub.n H in which R has at least about 8 carbon atoms and is a straight or branched chain saturated aliphatic hydrocarbyl group or a straight or branched chain monoolefinically or a poly-olefinically unsaturated hydrocarbyl group having from 1 to 3 olefinic double bonds, and in which n is in the range of about 2 to about 50, or a solution or suspension thereof; and d) at least one water-soluble or water-dispersible N-hydrocarbyl pyridinium halide having up to about 24 carbon atoms in the molecule, and wherein (i) the hydrocarbyl group attached to the nitrogen atom of the heterocyclic aromatic ring of the pyridinium nucleus is a saturated or olefinically unsaturated aliphatic hydrocarbyl group having in the range of about 4 to about 18 carbon atoms, and (ii) the ring carbon atoms of the pyridinium nucleus itself are either unsubstituted or one or more of such ring carbon atoms are substituted with a short chain alkyl group of up to about 4 carbon atoms, or a solution or suspension thereof; ingredient a) being the only herbicide or plant growth regulant used in forming said composition, and ingredients b), c) and d) being the only surfactants used in forming said composition; and e) optionally, one or more agriculturally acceptable substances none of which is a herbicide, or a plant growth regulant or a surfactant. ### Claim 32 (depends on 31) A method according to claim 31 wherein said herbicide or plant growth regulant composition is a water solution, and wherein said composition is applied to the foliage by spraying the water solution onto the foliage. ### Claim 33 (depends on 31) A method according to claim 31 wherein said herbicide or plant growth regulant composition is in the form of a powder, and wherein said composition is applied to the foliage as a foliar dust. ### Claim 34 (depends on 31) A method according to claim 31 wherein ingredient a) is an amine, ammonium, alkali metal, alkylsulfonium, alkylphosphonium, sulfonylamine, and/or aminoguanidine salt of glyphosate. ### Claim 35 (depends on 31) A method according to claim 31 wherein ingredient b) is tetradecyldimethylamine oxide, ingredient c) is a mixture of ethoxylated lauryl, myristic and cetyl alcohols with an average of about 9 ethylene oxide units per molecule, and ingredient d) is N-dodecylpyridinium bromide .