WO2001008482A1 - Herbicidal compositions - Google Patents
Herbicidal compositions Download PDFInfo
- Publication number
- WO2001008482A1 WO2001008482A1 PCT/GB2000/002865 GB0002865W WO0108482A1 WO 2001008482 A1 WO2001008482 A1 WO 2001008482A1 GB 0002865 W GB0002865 W GB 0002865W WO 0108482 A1 WO0108482 A1 WO 0108482A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- weight
- alkyl
- surfactant
- glyphosate
- solution
- Prior art date
Links
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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
Definitions
- the present invention relates to concentrated herbicidal compositions comprising water soluble glyphosate salts and a surfactant.
- Factors governing the choice of surfactant include wetting power, herbicidal or synergistic action, environmental profile and ability to form stable solutions with glyphosate at as high a concentration as possible, as well as cost. A particularly important factor is low foaming. Most surfactants cause undesirable foam levels. These not only make handling more difficult but also impair biocidal effectiveness.
- ether carboxylates meet most of the above criteria and in particular give enhanced biocidal action but are insufficiently soluble in concentrated glyphosate solutions.
- betaines can solubilise ether carboxylates, but that high salt levels normally associated with betaines tend to precipitate glyphosate.
- Desalted betaines are available but are expensive.
- certain alkyl amido amine oxides also meet most of the above criteria and in addition are soluble and can act as cosurfactants, solubilising ether carboxylates. The trihydrocarbyl amine oxides are not readily compatible with ether carboxylates.
- the invention provides a herbicidal solution concentrate comprising from 30% by weight, to saturation of a water soluble glyphosate salt and from 8 to 20% by weight of surfactant comprising: 10 to 100% by weight based on the total weight of surfactant of an alkyl and/or alkenyl amido amine oxide of the formula:
- R is a C ⁇ - 20 alkyl or alkenyl group
- m is 1 to 4
- p and q are independently 0 to 3; and from 0 to 90% by weight based on the total weight of surfactant of ether carboxylate.
- the glyphosate is preferably present as its potassium, ammonium, C 2 to 3 amine or mono or di ethanolamine salt, or as a mixture of two or more of said salts. Particularly preferred is the isopropylamine salt.
- (m + the number of carbon atoms in R) is from 7 to 19 and that p and q are each 0.
- m is 2 or most preferably 3.
- R is desirably 8 or 10.
- Amine oxides in which the majority of the amido alkyl groups are of the same length are particularly preferred.
- the amine oxide may optionally be derived from a coconut or palm fatty acid, especially one which has been "topped", i.e. has had the higher mol weight constituents such as C 14 +, removed or reduced.
- the amine oxide should constitute at least 20 and preferably more than
- the presence of an ether carboxylate is preferred, since it provides enhanced biocidal activity.
- the ether carboxylate preferably constitutes at least 10% , more preferably greater than 20, especially more than 30% of the total weight of surfactant.
- the ether carboxylate is an alkyl alkenyl or alkaryl poly alkoxy carboxylate such as RO[(CH 2 ) n O] m CH 2 CO " where R is an alkyl, alkenyl or alkyl phenyl group having from 8 to 20 aliphatic carbon atoms, each n is 2 to 4, preferably 2 and m is 1 to 30, preferably 2 to 20, e.g. 3 to 10.
- the counter ion may comprise sodium but is preferably potassium or ammonium or an amine e.g. a C 2 to 3 amine or an alkanolamine. We particularly prefer narrow cut C 8 and C 10 alkyl polyethoxy carboxylates.
- the surfactant may additionally comprise an amphoteric surfactant.
- the amphoteric surfactant may for example be a betaine, e.g. a betaine of the formula: Rs ⁇ CF ⁇ COO, wherein each R is an alkyl, cycloalkyl, alkenyl or alkaryl group and preferably at least one, and most preferably not more than one R, has an average of from 6 to 14, e.g. 8 to 10 aliphatic carbon atoms and each other R has an average of from 1 to 4 carbon atoms. It may also comprise a so called "imidazoline" betaine traditionally ascribed the formula:
- R and R' are alkyl, alkenyl, cycloalkyl, alkaryl or alkanol groups having an average of from 1 to 20 aliphatic carbon atoms and R preferably has an average of from 6 to 20, e.g. 8 to 14 aliphatic carbon atoms and R 1 preferably has 1 to 4 carbon atoms.
- imidazoline betaines are normally present substantially entirely as the non-cylic N-amido-alkyl betaine.
- amphoteric surfactants for use according to our invention include alkyl amino polyalkoxy sulphates, sulphobetaines and other quaternary amine or quaternised imidazoline sulphonic acids and their salts, and Zwitterionic surfactants, e.g. N-alkyl taurines, carboxylated amido amines such as RCONH(CH 2 ) n N + R' CH 2 CO " 2 where n is 2 to 4, and amino acids having, in each case, hydrocarbon groups capable of conferring surfactant properties (e.g. alkyl, cycloalkyl alkenyl or alkaryl groups having from 8 to 20 aliphatic carbon atoms).
- Zwitterionic surfactants e.g. N-alkyl taurines, carboxylated amido amines such as RCONH(CH 2 ) n N + R' CH 2 CO " 2 where n is 2 to 4, and amino acids having, in each case, hydrocarbon groups capable of confer
- Typical examples include 2-tallow alkyl, 1 -tallow amido alkyl, 1-carboxymethyl imidazoline, 2-coconut alkyl N-carboxymethyl 2 (hydroxyalkyl) imidazoline, coconut amido propyl dimethyl betaine and C 12-14 alkyl dimethyl betaine.
- any water soluble amphoteric or Zwitterionic surfactant compound which comprises a hydrophobic portion including C 8-20 alkyl or alkenyl group and a hydrophilic portion containing an amine or quaternary ammonium group and a carboxylate, sulphate or sulphonic acid group may be used in our invention.
- the amphoteric surfactant may constitute from 0 to 90% more usually less than 90%, preferably less than 70%, especially less than 50% by weight of the total surfactant.
- an amphoteric surfactant is selected to use a low sodium version, to avoid precipitation of sodium glyphosphate.
- concentration of sodium ion in the composition should be less than 0.035% based on the total weight of the composition.
- the surfactant consist essentially of the amine oxide, ether carboxylate and, optionally, the amphoteric surfactant.
- non-ionic surfactants including alkylethoxylates and alkanolamides
- anionic surfactants such as alkyl ether sulphates, alkyl sulphates, alkyl benzene sulphonates and soaps.
- the formulation may conveniently contain chelating or sequestering agents to enhance the performance of the product in hard water.
- calcium and/or magnesium sequestrants such as phosphates, polyphosphates, polycarboxylates, amino carboxylates, phosphonates and, in particular, amino phophonates, may be present in effective amounts.
- Specific examples include potassium pyrophosphate, sodium tripolyphosphate, ammonium hexametaphosphate, citric acid, polyacrylic acid nitrilotriacetic acid, ethylene diamine tetracetic acid, acetodiphosphonic acid, amino tris (methylenephosphonic) acid, ethylene diamine tetrakis (methylene phosphonic) acid and especially diethylene triamine pentakis (methylene phosphonic) acid.
- the chelant may be present in the acid form or as a water soluble salt, however for reasons stated above we prefer that the amount of sodium be limited: We therefore prefer that the chelant if present as a salt be present as the potassium or more preferably ammonium salt or as an amine or alkalolamine salt.
- the chelant is preferably present in concentrations of from 0.05 to 5% especially 0.1 to 1% e.g. 0.2 to 0.5%o.
- the solution concentrate does not normally require the presence of solvents, however they can be tolerated and may be adventitiously present as constituents of surfactant blends used to prepare the solution concentrates.
- the blends contain: from 10 to 70% more preferably 20 to 60% e.g. 30 to 50% ether carboxylate by weight of the blend; from 20 to 80% more preferably 30 to 10% e.g. 40 to 60% of the amidoalkyl amine oxide by weight of the blend; and from 3 to 50% more preferably 5 to 40% e.g. 10 to 30%, by weight of the blend, of solvent.
- the solvent is typically a water miscible mono, di- or polyhydric alcohol or glycol ether such as ethanol, ispropanol, ethylene glycol, glycerol, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether or preferably polyethylene glycol.
- a polyethylene glycol with a mean molecular weight of from 90 to 300, e.g. 130 to 250.
- the surfactant blend may optionally contain minor amounts of hydrotrope such as a Ci to 5 alkyl benzene sulphonate e.g. a potassium, ammonium or amine xylene sulphonate, if required to inhibit gelling.
- hydrotrope such as a Ci to 5 alkyl benzene sulphonate e.g. a potassium, ammonium or amine xylene sulphonate, if required to inhibit gelling.
- a Ci to 5 alkyl benzene sulphonate e.g. a potassium, ammonium or amine xylene sulphonate
- the invention provides the use of blends of ether carboxylate and amidoalkyl amine oxide to prepare glyphosphate solution concentrates and to such blends for use in preparing the concentrates and to sprayable solutions prepared by diluting the solution concentrate with water.
- the pH of the solution concentrate be adjusted to from 3 to 7 preferably 4 to 6 e.g. 4.5 to 5.5 with a base that does not precipitate glyphosate, such as ammonia or an amine.
- the invention will be illustrated by the following examples in which the glyphosate was used as the isopropylamine salt and weights of glyphosate are all quoted as gm acid equivalent per litre solution. Surfactants and glycol are all quoted as g. active matter per litre of solution.
- EPICOL is a Registered Trade Mark of Albright & Wilson UK Limited
- CVE is C 8 alkyl 5 mole ethoxy carboxylate
- CVH is C 8 alkyl 8 mole ethoxy carboxylate
- C 8 amido amine oxide is N-octanoamidopropyl-N,Ndimethylamine oxide
- each of the above formulations was a clear, stable solution which gave very low foam in comparison to the standard commercial product.
- the formulation was prepared from a blend of the ether carboxylate (which is supplied as 85% aqueous solution) amine oxide (as 40% aqueous solution) and any solvent, chelant or wetting agent.
- the blends were stable and dispersed easily in water together with the glyphosate.
- the pH of the formulation was finally adjusted with ammonia.
Landscapes
- 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
Description
Claims
Priority Applications (11)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA002378094A CA2378094A1 (en) | 1999-07-31 | 2000-07-28 | Herbicidal compositions |
AU61719/00A AU6171900A (en) | 1999-07-31 | 2000-07-28 | Herbicidal compositions |
DE60003317T DE60003317T2 (en) | 1999-07-31 | 2000-07-28 | HERBICIDAL COMPOSITIONS |
NZ516293A NZ516293A (en) | 1999-07-31 | 2000-07-28 | Herbicidal compositions containing surfactants of alkyl and/or alkenyl amido amine oxides |
MXPA01013332A MXPA01013332A (en) | 1999-07-31 | 2000-07-28 | Herbicidal compositions. |
DK00948152T DK1206182T3 (en) | 1999-07-31 | 2000-07-28 | Herbicidal compositions |
US10/018,556 US6645912B1 (en) | 1999-07-31 | 2000-07-28 | Herbicidal compositions |
BR0011901-6A BR0011901A (en) | 1999-07-31 | 2000-07-28 | Herbicidal compositions |
AT00948152T ATE242595T1 (en) | 1999-07-31 | 2000-07-28 | HERBICIDAL COMPOSITIONS |
JP2001513230A JP2003505478A (en) | 1999-07-31 | 2000-07-28 | Herbicide composition |
EP00948152A EP1206182B1 (en) | 1999-07-31 | 2000-07-28 | Herbicidal compositions |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9917976.4 | 1999-07-31 | ||
GBGB9917976.4A GB9917976D0 (en) | 1999-07-31 | 1999-07-31 | Herbicidal compositions |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2001008482A1 true WO2001008482A1 (en) | 2001-02-08 |
Family
ID=10858277
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/GB2000/002865 WO2001008482A1 (en) | 1999-07-31 | 2000-07-28 | Herbicidal compositions |
Country Status (18)
Country | Link |
---|---|
US (1) | US6645912B1 (en) |
EP (1) | EP1206182B1 (en) |
JP (1) | JP2003505478A (en) |
AR (1) | AR025007A1 (en) |
AT (1) | ATE242595T1 (en) |
AU (1) | AU6171900A (en) |
BR (1) | BR0011901A (en) |
CA (1) | CA2378094A1 (en) |
DE (1) | DE60003317T2 (en) |
DK (1) | DK1206182T3 (en) |
ES (1) | ES2199840T3 (en) |
GB (1) | GB9917976D0 (en) |
HU (1) | HUP0202348A2 (en) |
MX (1) | MXPA01013332A (en) |
NZ (1) | NZ516293A (en) |
PT (1) | PT1206182E (en) |
UY (1) | UY26264A1 (en) |
WO (1) | WO2001008482A1 (en) |
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1366662A1 (en) * | 2002-05-31 | 2003-12-03 | Kao Corporation | Enhancer for agricultural chemicals |
WO2004107862A1 (en) * | 2003-06-04 | 2004-12-16 | Clariant Gmbh | Preparations comprising amine oxides and anionic surfactants |
US6992046B2 (en) | 2002-01-29 | 2006-01-31 | Rhodia Chimie | Concentrated aqueous phytopathological formulation comprising a herbicide and a betaine type surfactant |
WO2006069794A3 (en) * | 2004-12-30 | 2006-10-12 | Rhodia Chimie Sa | Herbicidal composition comprising an aminophosphate or aminophosphonate salt, a betaine and an amine oxide |
WO2007059107A2 (en) | 2005-11-14 | 2007-05-24 | Rhodia Inc. | Agricultural adjuvant compositions, pesticide compositions, and methods for using such compositions |
EP2235134A1 (en) * | 2007-12-21 | 2010-10-06 | Huntsman Petrochemical LLC | Method of preparing amidoamine alkoxylates and compositions thereof |
WO2011029561A2 (en) | 2009-09-10 | 2011-03-17 | Clariant International Ltd | Pesticide preparations |
WO2010036996A3 (en) * | 2008-09-29 | 2011-03-24 | Monsanto Technology Llc | Glyphosate formulations containing amidoalkylamine surfactants |
WO2012061106A1 (en) | 2010-10-25 | 2012-05-10 | Stehpan Company | Glyphosate formulations based on compositions derived from natural oil metathesis |
US8236730B2 (en) | 2002-01-29 | 2012-08-07 | Rhodia Chimie | Aqueous herbicidal concentrate comprising a betaine type surfactant |
US8841235B2 (en) | 2010-08-10 | 2014-09-23 | Rhodia Operations | Agricultural pesticide compositions |
AU2013224661B2 (en) * | 2005-11-14 | 2015-05-28 | Specialty Operations France | Agricultural adjuvant compositions, pesticide compositions, and methods for using such compositions |
WO2021007683A1 (en) * | 2019-07-12 | 2021-01-21 | Rhodia Operations | Stable herbicidal compositions comprising amine oxide and betaine |
WO2021219680A1 (en) * | 2020-04-30 | 2021-11-04 | Nouryon Chemicals International B.V. | Alkyl polyamine polyglycerol surfactants |
US11452289B2 (en) | 2016-05-11 | 2022-09-27 | Monsanto Technology Llc | Glyphosate formulations containing amidoalkylamine surfactants |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7060661B2 (en) * | 1997-12-19 | 2006-06-13 | Akzo Nobel N.V. | Acid thickeners and uses thereof |
US7358215B1 (en) | 1999-09-07 | 2008-04-15 | Akzo Nobel Surface Chemistry Llc | Quaternary ammonium salts as thickening agents for aqueous systems |
DK1212385T3 (en) * | 1999-09-07 | 2016-04-04 | Akzo Nobel Surface Chem | Quaternary ammonium salts as thickeners for aqueous systems |
DE602005011454D1 (en) | 2004-08-19 | 2009-01-15 | Monsanto Technology Llc | HERBICIDE GLYPHOSATE SALT COMPOSITION |
NZ564145A (en) * | 2005-05-17 | 2009-12-24 | Rhodia | Agricultural adjuvant compositions comprising a betaine surfactant and glycerol, herbicide compositions, and methods for using such compositions |
MX2007014869A (en) * | 2005-05-24 | 2008-02-15 | Monsanto Technology Llc | Herbicide compatibility improvement. |
CA2649977C (en) * | 2006-06-14 | 2016-05-03 | Eureka Agresearch Pty Ltd. | Herbicidal composition and method for removing unwanted foliage |
US20100029483A1 (en) | 2006-10-16 | 2010-02-04 | Rhodia Inc. | Agricultural adjuvant compositions, pesticide compositions, and methods for using such compositions |
FR2914647B1 (en) * | 2007-04-05 | 2011-10-21 | Rhodia Recherches Et Tech | COPOLYMER COMPRISING BETAINIC UNITS AND HYDROPHOBIC AND / OR AMPHIPHILIC UNITS, PREPARATION METHOD, AND USES. |
EP2214479A2 (en) * | 2007-11-07 | 2010-08-11 | Rhodia Opérations | Herbicidal composition comprising an aminophosphate or aminophosphonate salt and a viscosity reducing agent |
EP2306819B1 (en) * | 2008-06-18 | 2016-03-09 | Stepan Company | Ultra-high loading glyphosate concentrate |
BRPI1016228B1 (en) * | 2009-03-06 | 2021-02-09 | Syngenta Participations Ag | compatibilized aqueous pesticide formulation, method of inhibiting at least one pest in a harvest area and method of forming said aqueous formulation |
BR112012001048A8 (en) | 2009-07-14 | 2017-04-18 | Rhodia Operations | AGRICULTURAL ADJUVANT COMPOSITIONS, PESTICIDE COMPOSITIONS, AND METHODS OF USE OF SUCH COMPOSITIONS. |
WO2011026800A2 (en) * | 2009-09-02 | 2011-03-10 | Akzo Nobel Chemicals International B.V. | Nitrogen containing surfactants for agricultural use |
US20220338474A1 (en) * | 2019-09-20 | 2022-10-27 | Rhodia Operations | Stable herbicidal compositions comprising amine oxide and tertiary amine |
CN114794099A (en) | 2021-01-19 | 2022-07-29 | 诺力昂化学品国际有限公司 | Nitrogen-containing surfactants for use in agriculture |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0508667A1 (en) * | 1991-04-10 | 1992-10-14 | Monsanto Company | Aqueous agricultural compositions, methods of making them and their use |
EP0560570A2 (en) * | 1992-03-09 | 1993-09-15 | Amway Corporation | Liquid dishwashing detergent |
WO1997036491A1 (en) * | 1996-04-03 | 1997-10-09 | Albemarle Corporation | Herbicidal and plant growth regulant compositions and their use |
WO2000038523A1 (en) * | 1998-12-23 | 2000-07-06 | Rhodia Consumer Specialties Limited | Herbicidal compositions and surfactant concentrates |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0824314B1 (en) * | 1996-03-01 | 2002-09-25 | Kao Corporation | Efficacy enhancer for agricultural chemicals and agricultural chemical compositions |
BR9810811B1 (en) * | 1997-07-22 | 2011-02-08 | concentrated aqueous ammonium glyphosate herbicidal compositions and method for killing or controlling vegetation. |
-
1999
- 1999-07-31 GB GBGB9917976.4A patent/GB9917976D0/en not_active Ceased
-
2000
- 2000-07-28 DK DK00948152T patent/DK1206182T3/en active
- 2000-07-28 EP EP00948152A patent/EP1206182B1/en not_active Expired - Lifetime
- 2000-07-28 PT PT00948152T patent/PT1206182E/en unknown
- 2000-07-28 ES ES00948152T patent/ES2199840T3/en not_active Expired - Lifetime
- 2000-07-28 CA CA002378094A patent/CA2378094A1/en not_active Abandoned
- 2000-07-28 BR BR0011901-6A patent/BR0011901A/en not_active Application Discontinuation
- 2000-07-28 US US10/018,556 patent/US6645912B1/en not_active Expired - Fee Related
- 2000-07-28 AT AT00948152T patent/ATE242595T1/en not_active IP Right Cessation
- 2000-07-28 AU AU61719/00A patent/AU6171900A/en not_active Abandoned
- 2000-07-28 HU HU0202348A patent/HUP0202348A2/en unknown
- 2000-07-28 JP JP2001513230A patent/JP2003505478A/en not_active Withdrawn
- 2000-07-28 WO PCT/GB2000/002865 patent/WO2001008482A1/en active IP Right Grant
- 2000-07-28 MX MXPA01013332A patent/MXPA01013332A/en not_active Application Discontinuation
- 2000-07-28 NZ NZ516293A patent/NZ516293A/en unknown
- 2000-07-28 DE DE60003317T patent/DE60003317T2/en not_active Expired - Fee Related
- 2000-07-31 UY UY26264A patent/UY26264A1/en not_active Application Discontinuation
- 2000-08-01 AR ARP000103969A patent/AR025007A1/en unknown
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0508667A1 (en) * | 1991-04-10 | 1992-10-14 | Monsanto Company | Aqueous agricultural compositions, methods of making them and their use |
EP0560570A2 (en) * | 1992-03-09 | 1993-09-15 | Amway Corporation | Liquid dishwashing detergent |
WO1997036491A1 (en) * | 1996-04-03 | 1997-10-09 | Albemarle Corporation | Herbicidal and plant growth regulant compositions and their use |
WO2000038523A1 (en) * | 1998-12-23 | 2000-07-06 | Rhodia Consumer Specialties Limited | Herbicidal compositions and surfactant concentrates |
Cited By (33)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6992046B2 (en) | 2002-01-29 | 2006-01-31 | Rhodia Chimie | Concentrated aqueous phytopathological formulation comprising a herbicide and a betaine type surfactant |
US8236730B2 (en) | 2002-01-29 | 2012-08-07 | Rhodia Chimie | Aqueous herbicidal concentrate comprising a betaine type surfactant |
EP1366662A1 (en) * | 2002-05-31 | 2003-12-03 | Kao Corporation | Enhancer for agricultural chemicals |
US6897184B2 (en) | 2002-05-31 | 2005-05-24 | Kao Corporation | Enhancer for agricultural chemicals |
WO2004107862A1 (en) * | 2003-06-04 | 2004-12-16 | Clariant Gmbh | Preparations comprising amine oxides and anionic surfactants |
WO2006069794A3 (en) * | 2004-12-30 | 2006-10-12 | Rhodia Chimie Sa | Herbicidal composition comprising an aminophosphate or aminophosphonate salt, a betaine and an amine oxide |
US9045720B2 (en) | 2004-12-30 | 2015-06-02 | Rhodia Chimie | Herbicidal composition comprising an aminophosphate or aminophosphonate salt, a betaine and an amine oxide |
EP1951039A4 (en) * | 2005-11-14 | 2011-01-26 | Rhodia | Agricultural adjuvant compositions, pesticide compositions, and methods for using such compositions |
US9107405B2 (en) | 2005-11-14 | 2015-08-18 | Rhodia Operations | Agricultural adjuvant compostions, pesticide compositions, and methods for using such compositions |
WO2007059107A2 (en) | 2005-11-14 | 2007-05-24 | Rhodia Inc. | Agricultural adjuvant compositions, pesticide compositions, and methods for using such compositions |
AU2013224661B2 (en) * | 2005-11-14 | 2015-05-28 | Specialty Operations France | Agricultural adjuvant compositions, pesticide compositions, and methods for using such compositions |
EP2687090A3 (en) * | 2005-11-14 | 2014-02-19 | Solvay USA Inc. | Agricultural adjuvant compostions, pesticide compositions, and methods for using such compositions |
US8653001B2 (en) * | 2005-11-14 | 2014-02-18 | Rhodia Operations | Agricultural adjuvant compostions, pesticide compositions, and methods for using such compositions |
EP1951039A2 (en) * | 2005-11-14 | 2008-08-06 | Rhodia Inc. | Agricultural adjuvant compositions, pesticide compositions, and methods for using such compositions |
AU2006315513B2 (en) * | 2005-11-14 | 2013-06-13 | Specialty Operations France | Agricultural adjuvant compositions, pesticide compositions, and methods for using such compositions |
EP2235134A1 (en) * | 2007-12-21 | 2010-10-06 | Huntsman Petrochemical LLC | Method of preparing amidoamine alkoxylates and compositions thereof |
EP2235134A4 (en) * | 2007-12-21 | 2015-04-08 | Huntsman Petrochemical Llc | Method of preparing amidoamine alkoxylates and compositions thereof |
US11925179B2 (en) | 2008-09-29 | 2024-03-12 | Monsanto Technology Llc | Glyphosate formulations containing amidoalkylamine surfactants |
WO2010036996A3 (en) * | 2008-09-29 | 2011-03-24 | Monsanto Technology Llc | Glyphosate formulations containing amidoalkylamine surfactants |
DE102009041003A1 (en) | 2009-09-10 | 2011-03-24 | Clariant International Limited | pesticide preparations |
US8759255B2 (en) | 2009-09-10 | 2014-06-24 | Clariant Finance (Bvi) Limited | Pesticide preparations |
WO2011029561A2 (en) | 2009-09-10 | 2011-03-17 | Clariant International Ltd | Pesticide preparations |
US8841235B2 (en) | 2010-08-10 | 2014-09-23 | Rhodia Operations | Agricultural pesticide compositions |
US9006144B2 (en) | 2010-10-25 | 2015-04-14 | Stepan Company | Glyphosate formulations based on compositions derived from natural oil metathesis |
EP2632271A4 (en) * | 2010-10-25 | 2014-10-01 | Stepan Co | Glyphosate formulations based on compositions derived from natural oil metathesis |
AU2011323770B2 (en) * | 2010-10-25 | 2015-07-16 | Stepan Company | Glyphosate formulations based on compositions derived from natural oil metathesis |
EP2632271A1 (en) * | 2010-10-25 | 2013-09-04 | Stepan Company | Glyphosate formulations based on compositions derived from natural oil metathesis |
WO2012061106A1 (en) | 2010-10-25 | 2012-05-10 | Stehpan Company | Glyphosate formulations based on compositions derived from natural oil metathesis |
US11452289B2 (en) | 2016-05-11 | 2022-09-27 | Monsanto Technology Llc | Glyphosate formulations containing amidoalkylamine surfactants |
WO2021007683A1 (en) * | 2019-07-12 | 2021-01-21 | Rhodia Operations | Stable herbicidal compositions comprising amine oxide and betaine |
WO2021008300A1 (en) * | 2019-07-12 | 2021-01-21 | Rhodia Operations | Stable herbicidal compositions comprising amine oxide and betaine |
WO2021219680A1 (en) * | 2020-04-30 | 2021-11-04 | Nouryon Chemicals International B.V. | Alkyl polyamine polyglycerol surfactants |
CN115461435A (en) * | 2020-04-30 | 2022-12-09 | 诺力昂化学品国际有限公司 | Alkyl polyamine polyglycerol surfactants |
Also Published As
Publication number | Publication date |
---|---|
GB9917976D0 (en) | 1999-09-29 |
AU6171900A (en) | 2001-02-19 |
CA2378094A1 (en) | 2001-02-08 |
BR0011901A (en) | 2002-05-14 |
EP1206182A1 (en) | 2002-05-22 |
HUP0202348A2 (en) | 2002-11-28 |
JP2003505478A (en) | 2003-02-12 |
US6645912B1 (en) | 2003-11-11 |
UY26264A1 (en) | 2001-01-31 |
DE60003317D1 (en) | 2003-07-17 |
MXPA01013332A (en) | 2003-05-19 |
AR025007A1 (en) | 2002-11-06 |
ATE242595T1 (en) | 2003-06-15 |
EP1206182B1 (en) | 2003-06-11 |
PT1206182E (en) | 2003-10-31 |
NZ516293A (en) | 2002-11-26 |
ES2199840T3 (en) | 2004-03-01 |
DE60003317T2 (en) | 2004-02-12 |
DK1206182T3 (en) | 2003-09-22 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP1206182B1 (en) | Herbicidal compositions | |
US6653257B2 (en) | Herbicidal compositions and surfactant concentrates | |
JP3403414B2 (en) | Liquid composition for stabilizing amino acid herbicides | |
US6992046B2 (en) | Concentrated aqueous phytopathological formulation comprising a herbicide and a betaine type surfactant | |
AU2005321478B2 (en) | Herbicidal composition comprising an aminophosphate or aminophosphonate salt and a betaine | |
AU2008324145B2 (en) | Herbicidal composition comprising an aminophosphate or aminophosphonate salt and a viscosity reducing agent | |
US8236730B2 (en) | Aqueous herbicidal concentrate comprising a betaine type surfactant | |
NZ240081A (en) | Stable aqueous composition comprising glyphosate, a silicone copolymer and a surfactant | |
HUT54023A (en) | Process for producing liquide plant protecting composition | |
EP1164845B1 (en) | Agrochemical composition | |
ZA200200696B (en) | Hybrid ionic phosphorus surfactant adjuvants for bioactive compositions. | |
WO2014071475A1 (en) | Surfactant composition that can be used in glyphosate-containing herbicide formulations, glyphosate-containing herbicide formulation, and use of the glyphosate-containing herbicide formulation |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CR CU CZ DE DK DM DZ EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT TZ UA UG US UZ VN YU ZA ZW |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
DFPE | Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101) | ||
WWE | Wipo information: entry into national phase |
Ref document number: 2000948152 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: PA/a/2001/013332 Country of ref document: MX |
|
WWE | Wipo information: entry into national phase |
Ref document number: 516293 Country of ref document: NZ |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2378094 Country of ref document: CA |
|
WWE | Wipo information: entry into national phase |
Ref document number: 61719/00 Country of ref document: AU |
|
WWE | Wipo information: entry into national phase |
Ref document number: 10018556 Country of ref document: US |
|
WWP | Wipo information: published in national office |
Ref document number: 2000948152 Country of ref document: EP |
|
REG | Reference to national code |
Ref country code: DE Ref legal event code: 8642 |
|
WWG | Wipo information: grant in national office |
Ref document number: 2000948152 Country of ref document: EP |