WO2003103396A1 - Fabrication et utilisation de d'une composition herbicide - Google Patents

Fabrication et utilisation de d'une composition herbicide Download PDF

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Publication number
WO2003103396A1
WO2003103396A1 PCT/US2002/018420 US0218420W WO03103396A1 WO 2003103396 A1 WO2003103396 A1 WO 2003103396A1 US 0218420 W US0218420 W US 0218420W WO 03103396 A1 WO03103396 A1 WO 03103396A1
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WO
WIPO (PCT)
Prior art keywords
herbicide
weight
acid
amount
carboxylic acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2002/018420
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English (en)
Inventor
Greg Volgas
Johnnie R. Roberts
Flavious Johnson
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Helena Chemical Co
Original Assignee
Helena Chemical Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Helena Chemical Co filed Critical Helena Chemical Co
Priority to PCT/US2002/018420 priority Critical patent/WO2003103396A1/fr
Priority to AU2002312442A priority patent/AU2002312442A1/en
Publication of WO2003103396A1 publication Critical patent/WO2003103396A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
    • A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
    • A01N39/04—Aryloxy-acetic acids; Derivatives thereof

Definitions

  • the invention pertains to a method for manufacture and use of a herbicidal formulation of chlorinated carboxylic acid herbicides.
  • esters are more likely to volatilize even after deposition onto target areas. After volatilization, these esters can cause significant damage to off-target plants.
  • Chlorinated carboxylic acid herbicides are usually have traditionally been reacted into amine or other salts, which are soluble in water, or into esters which are oil soluble. Both salts and esters must then break down in the environment back into the acid, which is herbicidal. It would be preferable, then, to apply the herbicides as acids. However, they are not significantly soluble in water.
  • solvents used to formulate 2,4-D acid such as xylene range hydrocarbons, are known to be phytotoxic to plants and may enhance herbicide volatility and subsequent drift to non-target areas.
  • Albaugh D-638 is one such product, but it further incorporates the ester form of 2,4-D into the formulation.
  • the formulation is 24.5 % by weight of 2-butoxethyl ester of 2,4-dichlorophenoxyacetic acid (CAS # 1929-73-3), 13.8% by weight 2, 4-D (CAS # 94-75-7) and a solvent that contains 7.7 % by weight naphthalene (CAS # 91-20-3). It is believed that the solvent is Aromatic 150. It is believed that solvent is present in an amount from 55 to 60%.
  • Another commercial product containing the acid form of 2,4-dichlorophenoxyacetic acid is WEEDONE® 638 from Rhone Poulenc (now marketed by Nufarm).
  • This formulation contains 25.2% of the 2-ethylhexyl ester of 2,4-D, 13.8% of the acid form of 2,4-D, 3% propylene glycol, 1.5% titanium oxide and other undisclosed inerts.
  • This formulation is believed to be described in one of the following patents: US 5254344, US 5096711, or US 5206021.
  • the 2,4-D in this formulation is not solubolized, but has been dispersed through a water phase.
  • Another problem associated with the amine salts of some chlorinated carboxylic acid herbicides is their inability to mix with fertilizers. 2,4-D amine herbicides cannot be mixed directly into Uran (urea-ammonia nitrate) fertilizer without some dilution in water.
  • One embodiment of the invention is a herbicide composition comprising at least one chlorinated carboxylic acid herbicide and at least one surfactant in an effective amount such that said chlorinated carboxylic acid herbicide is dissolved in the surfactant and said at least one surfactant is present in a quantity equal to or greater than said at least one chlorinated carboxylic acid herbicide.
  • Another embodiment of the invention is a herbicide composition
  • a herbicide composition comprising at least one fully solubolized chlorinated carboxylic acid herbicide and at least about 8 weight % of at least one surfactant.
  • the invention also related to a process to produce a herbicidical composition which comprises blending a fully solubolized acid herbicide with a surfactant to form a solution provided that said chlorinated carboxylic acid herbicide and surfactant are present in an amount of about 1 part by weight of chlorinated carboxylic acid herbicide to at least about 1.5 part by weight of surfactant.
  • one embodiment of the invention is a herbicide composition
  • a herbicide composition comprising at least one chlorinated carboxylic acid herbicide and at least one surfactant in an effective amount such that said chlorinated carboxylic acid herbicide is dissolved in the surfactant and said at least one surfactant is present in a quantity equal to or greater than said at least one chlorinated carboxylic acid herbicide.
  • Another embodiment of the invention is a herbicide composition comprising at least one fully solubolized chlorinated carboxylic acid herbicide and at least about 8 weight % of at least one surfactant.
  • the invention also related to a process to produce a herbicidical composition which comprises blending a fully solubolized acid herbicide with a surfactant to form a solution provided that said chlorinated carboxylic acid herbicide and surfactant are present in an amount of about 1 part by weight of chlorinated carboxylic acid herbicide to at least about 1.5 part by weight of surfactant.
  • Chlorinated carboxylic acid herbicides include, but are not limited to the acid forms of: Synthetic auxins including, but not limited to: Benzoic acids such as but not limited to chloramben and dicamba, Phenoxy-carboxylic acids such as but not limited to 2,4,5-trichlorophenoxy acetic acid, 2,4-dichlorophenoxy acetic acid, 2,4-dichlorophenoxy butyric acid, clomeprop, dichlorprop, dichlorprop-P, monochlorophenoxy acetic acid, monochlorophenoxy butyric acid, mecoprop, and mecoprop-P. Pyridine carboxylic acids such as but not limited to clopyralid, fluroxypyr, picloram and triclopyr. Quinoline carboxylic acids such as but not limited to quinclorac and quinmerac. These herbicides preferably have one of the following 3 general structures Structure 1:
  • R is an alkanoic or carboxylic acid group a,b,c, and d are independently -H, -CI, -NH 2 , -CH 3 , or -OCH 3 .
  • Structure 2 :
  • R is an alkanoic or carboxylic acid group and a,b and c are independently -H, -CI, -F, or NH 2 .
  • R is an alkanoic or carboxylic acid group and a is -CI, or -CH 3
  • Useful surfactants or solvents include but are not limited to: Alcohol alkoxylates including but not limited to: Based on branched and linear alcohols Those containing ethylene oxide or propylene oxide Alcohol alkoxylate sulfates, Alkylphenol alkoxylates including but not limited to : Nonylphenol and octylphenols.
  • Amines including but not limited to : Fatty amine alkoxylates such as but not limited to tallowamine alkoxylates, Betaine derivatives, Block polymers of ethylene and propylene glycol, Carboxylated alcohol or alkylphenol alkoxylates, Diols, including but not limited to Butanediols, Diphenyl sulfonate derivatives, Ethers, including but not limited to Butyl celluslove, Butyl carbitol, Ethoxylated amines, Ethoxylated fatty acids, Ethoxylated fatty esters and oils, Ethylene carbonate, Fatty esters, Glycerol esters, Glycols including but not limited to Propylene glycol, Ethylene glycol, Dipropylene glycol, Diethylene glycol, Phosphate ester surfactants
  • the formulations may also contain oil-based components.
  • the oil or oil substitutes include, but are not limited to: Alkylated fatty acid esters, include but are not limited to: Methylated fatty acids, include but not limited to: Methylated C6-C 19 fatty acids, Methylated Tall oil fatty acids, Methylated Oleic acid, Methylated Linoleic acid, Methylated Linolenic acid, Methylated Stearic acid, Methylated Palmitic acid, And blends thereof;
  • Ethylated fatty acids include but are not limited to: Ethylated C6-C 19 fatty acids, Ethylated Tall oil fatty acids, Ethylated Oleic acid, Ethylated Linoleic acid, Ethylated Linolenic acid, Ethylated Stearic acid, Ethylated Palmitic acid, And blends thereof;
  • Butylated fatty acids include but are not limited to: Butylated C6-C 19 fatty acids, Butylated Tall oil fatty acids, Butylated Oleic acid, Butylated Linoleic acid, Butylated Linolenic acid, Butylated Stearic acid, Butylated Palmitic acid, And blends thereof;
  • Alkylated natural oils include but are not limited to: Alkylated soybean oil, include but limited to: Methylated soybean oil, Ethylated soybean oil, Butylated soybean oil, And blends thereof;
  • Alkylated canola oil include but are not limited to: Methylated canola oil, Ethylated canola oil, Butylated canola oil, And blends thereof;
  • Alkylated coconut oil include but are not limited to: Methylated coconut oil, Ethylated coconut oil, Butylated coconut oil, And blends thereof;
  • Alkylated sunflower oil include but are not limited to: Methylated sunflower oil, Ethylated sunflower oil, Butylated sunflower oil, And blend thereof;
  • Hydrocarbon oils include but are not limited to : Mineral oils, including but are not limited to: Paraffinic mineral oils, Naphthenic mineral oils, Aromatic mineral oils, And blends thereof;
  • Vegetable oils include but are not limited to: Soybean oil, Canola oil, Cottonseed oil, And blends thereof;
  • Fatty acids include but are not limited to: C6-C19 fatty acids, Tall oil fatty acids, Oleic acid, Linoleic acid, Linolenic acid, Stearic acid, Palmitic acid, And blends thereof;
  • Epoxified seed oils include but are not limited to: Epoxified soybean oil and Other oils or oil substitutes
  • the formulation can contain at least one of the above oils or its equivalent.
  • the oil can also be a blend of at least two oils.
  • a surfactant or emulsifier must also be used if the composition is intended for aqueous based sprays.
  • the composition preferably contains (a) from about 1 to about 50% by weight of at least one chlorinated carboxylic acid herbicide, preferably about 5 to about 30% and most preferably about 10 to about 20% and (b) at least about 8% of a surfactant and preferably at least 10% by weight of a surfactant, more preferably at least 20% by weight of a surfactant, more preferably at least 30% by weight of a surfactant and even more preferably from at least 40% by weight of a surfactant and most preferably at least 50%) by weight of a surfactant.
  • the surfactant can be present in an amount from about 8 to about 99%, preferably about 50 to about 90%, and most preferably about 70 to about 80% and (c) Optionally other components.
  • the composition can further comprises an ester of (2,4- dichlorophenoxy)acetic acid.
  • the composition according to the invention preferably contains at most 25% by weight of an ester of (2,4- dichlorophenoxy)acetic acid, preferably at most about 15% by weight of an ester of (2,4-dichlorophenoxy)acetic acid, more preferably at most about 10% by weight of an ester of (2,4-dichlorophenoxy)acetic acid, most preferably at most about 5% by weight of an ester of (2,4-dichlorophenoxy)acetic acid and at most about 2% by weight of an ester of (2,4-dichlorophenoxy)acetic acid.
  • the herbicide composition can optionally contain an aromatic solvent.
  • the aromatic solvent is present preferably in an amount of at most 50%> by weight and more preferably at most 40%o by weight of an aromatic solvent and even more preferably at most 30% by weight of an aromatic solvent and even more preferably at most 20% by weight of an aromatic solvent and even more preferably at most 15%> by weight of an aromatic solvent and even more preferably at most 10%> by weight of an aromatic solvent and most preferably at most 5% by weight of an aromatic solvent.
  • the herbicide composition preferably contains a chlorinated carboxylic acid herbicide and a surfactant in the ratio of acid herbicide to surfactant from about 1 :6 to about 1:1.
  • the herbicide composition does not need to contain an alkylated fatty acid, alkylated plant derived oil and/or an alkylated animal derived oil.
  • Example 10 2,4-D P Acid technical 15.0% Cu Alcohol (3EO) Ethoxylate 85.0%
  • Example 11 2,4-D B acid technical 15.0% C ⁇ Alcohol (3EO) Ethoxylate 85.0%
  • the components are blended together and the technical dissolved entirely.
  • the solution formed contains less than 2% of precipitates and preferably 0%> precipitates.
  • these formulations are compatible with Uran 32 fertilizer.
  • Other pesticides could be formulated using this composition.
  • Fertilizers could be added to these compositions. All references discussed herein are incorporated by reference in their entirety for all useful purposes.

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention porte sur un procédé de fabrication et d'utilisation d'une composition d'herbicide à base d'acide carboxylique chloré, pour laquelle on a considéré jusqu'alors que différents solvants étaient utilisables. La découverte de l'invention porte sur la possibilité d'utiliser des tensio-actifs comme solvants de ces herbicides qui présentent ainsi une activité herbicide supérieure par comparaison aux formes usuelles à base de sels et d'esters.
PCT/US2002/018420 2002-06-11 2002-06-11 Fabrication et utilisation de d'une composition herbicide Ceased WO2003103396A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
PCT/US2002/018420 WO2003103396A1 (fr) 2002-06-11 2002-06-11 Fabrication et utilisation de d'une composition herbicide
AU2002312442A AU2002312442A1 (en) 2002-06-11 2002-06-11 Manufacture and use of a herbicide formulation

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US2002/018420 WO2003103396A1 (fr) 2002-06-11 2002-06-11 Fabrication et utilisation de d'une composition herbicide

Publications (1)

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WO2003103396A1 true WO2003103396A1 (fr) 2003-12-18

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6906004B2 (en) 2001-09-26 2005-06-14 Platte Chemical Co. Herbicide composition comprising herbicide compound in acid form and acidifying agent
EP1825750A1 (fr) * 2006-02-22 2007-08-29 Menno Chemie-Vertrieb GmbH Système pour distribuer des produits chimiques agricoles
WO2009013120A3 (fr) * 2007-07-23 2009-04-09 Basf Se Formulations liquides solubles de sels d'ammonium de quinclorac
WO2013189773A1 (fr) * 2012-06-21 2013-12-27 Basf Se Composition aqueuse comprenant du dicamba et un agent de lutte contre la dérive
CN113925063A (zh) * 2021-11-17 2022-01-14 林猷宪 一种含有机酸和矿物油的有机农作物除草剂及其制备方法

Citations (9)

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Publication number Priority date Publication date Assignee Title
JPS5885805A (ja) * 1981-11-18 1983-05-23 Sankyo Co Ltd イネの登熟促進剤
US4470840A (en) * 1980-10-30 1984-09-11 Biochemical Research Corporation 1-Triacontanol plant growth stimulator formulations
EP0371212A2 (fr) * 1988-11-30 1990-06-06 American Cyanamid Company Micro-émulsions herbicides à base d'eau
EP0554015A1 (fr) * 1992-01-28 1993-08-04 Ishihara Sangyo Kaisha, Ltd. Suspension herbicide à base d'huile chimiquement stabilisée
WO1994000986A1 (fr) * 1992-07-01 1994-01-20 Church & Dwight Company, Inc. Compositions permettant de moduler la croissance vegetale
RU2073974C1 (ru) * 1993-02-04 1997-02-27 Научно-исследовательский институт гербицидов и регуляторов роста растений с опытно-экспериментальным производством Гербицидный состав
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WO1997037978A1 (fr) * 1996-04-09 1997-10-16 Dowelanco Herbicides a base de 5-polycyclylpyrimidine, substitues en position 4
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US4470840A (en) * 1980-10-30 1984-09-11 Biochemical Research Corporation 1-Triacontanol plant growth stimulator formulations
JPS5885805A (ja) * 1981-11-18 1983-05-23 Sankyo Co Ltd イネの登熟促進剤
EP0371212A2 (fr) * 1988-11-30 1990-06-06 American Cyanamid Company Micro-émulsions herbicides à base d'eau
EP0554015A1 (fr) * 1992-01-28 1993-08-04 Ishihara Sangyo Kaisha, Ltd. Suspension herbicide à base d'huile chimiquement stabilisée
WO1994000986A1 (fr) * 1992-07-01 1994-01-20 Church & Dwight Company, Inc. Compositions permettant de moduler la croissance vegetale
RU2073974C1 (ru) * 1993-02-04 1997-02-27 Научно-исследовательский институт гербицидов и регуляторов роста растений с опытно-экспериментальным производством Гербицидный состав
US5670454A (en) * 1994-12-15 1997-09-23 Basf Aktiengesellschaft Herbicides of the auxin type for treating transgenic crop plants
WO1997037978A1 (fr) * 1996-04-09 1997-10-16 Dowelanco Herbicides a base de 5-polycyclylpyrimidine, substitues en position 4
US5877112A (en) * 1997-08-27 1999-03-02 Helena Chemical Company Agricultural formulation

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* Cited by examiner, † Cited by third party
Title
DATABASE WPI Section Ch Week 198326, Derwent World Patents Index; Class C02, AN 1983-62632K, XP002209420 *
DATABASE WPI Section Ch Week 199740, Derwent World Patents Index; Class C03, AN 1997-433301, XP002209419 *

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7776790B2 (en) 2001-09-26 2010-08-17 Platte Chemical Co. Herbicide compositions comprising suspension concentrate with glyphosate acid, methods of preparation, and methods of use
US7094735B2 (en) 2001-09-26 2006-08-22 Platte Chemical Co. Herbicide microemulsion-forming-concentrates, microemulsions, and methods
US9237746B2 (en) 2001-09-26 2016-01-19 Platte Chemical Co. Herbicide composition comprising herbicide compound in acid form
US6906004B2 (en) 2001-09-26 2005-06-14 Platte Chemical Co. Herbicide composition comprising herbicide compound in acid form and acidifying agent
EP1825750A1 (fr) * 2006-02-22 2007-08-29 Menno Chemie-Vertrieb GmbH Système pour distribuer des produits chimiques agricoles
US20100255992A1 (en) * 2007-07-23 2010-10-07 Basf Se Soluble Liquid Formulations of Quinclorac Ammonium Salts
CN101778564A (zh) * 2007-07-23 2010-07-14 巴斯夫欧洲公司 二氯喹啉酸铵盐的可溶性液体配制剂
US8778840B2 (en) 2007-07-23 2014-07-15 Basf Se Soluble liquid formulations of quinclorac ammonium salts
CN101778564B (zh) * 2007-07-23 2014-09-10 巴斯夫欧洲公司 二氯喹啉酸铵盐的可溶性液体配制剂
WO2009013120A3 (fr) * 2007-07-23 2009-04-09 Basf Se Formulations liquides solubles de sels d'ammonium de quinclorac
WO2013189773A1 (fr) * 2012-06-21 2013-12-27 Basf Se Composition aqueuse comprenant du dicamba et un agent de lutte contre la dérive
US9451767B2 (en) 2012-06-21 2016-09-27 Basf Se Aqueous composition comprising dicamba and a drift control agent
CN113925063A (zh) * 2021-11-17 2022-01-14 林猷宪 一种含有机酸和矿物油的有机农作物除草剂及其制备方法

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