WO1999021423A1 - Composition herbicide comprenant du glyphosate et un n-acyle-sarcosinate - Google Patents

Composition herbicide comprenant du glyphosate et un n-acyle-sarcosinate Download PDF

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Publication number
WO1999021423A1
WO1999021423A1 PCT/IE1998/000086 IE9800086W WO9921423A1 WO 1999021423 A1 WO1999021423 A1 WO 1999021423A1 IE 9800086 W IE9800086 W IE 9800086W WO 9921423 A1 WO9921423 A1 WO 9921423A1
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WO
WIPO (PCT)
Prior art keywords
composition according
surfactant
herbicidal composition
glyphosate
herbicidal
Prior art date
Application number
PCT/IE1998/000086
Other languages
English (en)
Inventor
Brian Parker
Original Assignee
Brian Parker
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 Brian Parker filed Critical Brian Parker
Priority to AU96418/98A priority Critical patent/AU9641898A/en
Priority to EP98950276A priority patent/EP1024699A1/fr
Publication of WO1999021423A1 publication Critical patent/WO1999021423A1/fr

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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
    • 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 herbicidal glyphosate compositions, exhibiting greatly reduced eye irritancy, when compared to commercial glyphosate compositions.
  • Glyphosate or N-phosphonomethyl glycine is well-known as a broad-spectrum herbicide. It acts as a postemergent herbicide which is translocated within plants.
  • Typical commercial formulations contain about 41% of the isopropylamine salt of glyphosate and about 5%-20% by weight of a tallow amine ethoxylated surfactant.
  • Surfactants are typically incorporated into the formulation to improve the efficacy of glyphosate. These surfactants are termed activating surfactants.
  • the term surfactant may include a number of compounds. For example, with ethoxylated surfactants the degree of ethoxylation can be and typically is a statistical mixture. Numerous studies have been made on the effect of additives on the herbicidal activity of glyphosate. For example Wyrill and Burnside , Weed Science, Vol 25 (1977), 275-287, examined solutions containing different classes of surfactant, including 2 and 15 oxyethylene units. Some classes of surfactant were more effective than others in enhancing the herbicidal activity of glyphosate. However, Wyrill and Burnside concluded that a surfactant is a critical component of any glyphosate spray mixture.
  • Ethoxylated alkyl amine surfactants present in glyphosate formulations have been observed to greatly increase the corrosivity or irritancy of the composition to the eyes.
  • the level of irritancy is such that commercially formulated glyphosate solutions containing ethoxylated alkyla ine surfactants must be labelled as an irritant.
  • WO 97/03560 of Hampshire Chemical Corporation discloses herbicidal fluazifop-butyl (or fluazifop-P-butyl) compositions containing a C ft to C ?? sarcosinate or sarcosinate salt, such as sodium cocoyl sarcosinate, sodium lauroyl sarcosinate or combinations thereof.
  • the sarcosinate may be used at concentrations of 0.1 to 3.0% v/v in the formulation.
  • W0 97/03560 does mention lower irritancy and lower toxicity which may be attributed to the use of an aqueous solvent instead of an organic solvent which had been previously necessary to provide a solution of fluazifop-P-butyl.
  • W0 97/03560 contains no teaching about herbicidal glyphosate compositions. It could not be foreseen whether the use of a sarcosinate or sarcosinate salt in glyphosate compositions would have an adverse effect on the efficacy of glyphosate as the herbicide fluazifop-butyl is substantially different in its chemical structure and its mode of herbicidal action from glyphosate. Sarcosinates are themselves classified as eye irritants when in a 30% w/w aqueous solution.
  • the present invention provides a herbicidal composition comprising :
  • R represents an optionally substituted, saturated or unsaturated hydrocarbyl C,-C 4f) group for example an alkyl or alkenyl group having up to 40 carbon atoms
  • M is H or a positively charged counter ion.
  • compositions with the particular combination of glyphosate and an N-acyl sarcosinate surfactant demonstrates reduced eye irritancy as compared to conventional glyphosate compositions.
  • the herbicidal compositions of the present invention utilising N-acyl sarcosinates at a much-reduced level as a percentage weight of the total formulation compared to conventional surfactants, exhibit no loss of efficacy.
  • conventional surfactants are used at 6 to 17% by weight of the total formulation.
  • the sarcosinate surfactant used in the composition of the present invention may be used at concentrations as low as 0.1% to 2% of the total formulation.
  • the eye irritancy of such compositions has been found to be greatly reduced, which is surprising as formulations traditionally carry irritancy labels and the solvent has not been changed.
  • the compositions of the present invention do not need to be labelled as irritants.
  • R preferably has 8 to 22 carbon atoms, more preferably 10 to 18 carbon atoms.
  • R may be straight chain or branched and may be substituted with halogen, preferably Cl or F, or OH or an alkoxy group, a carboxylic acid derivative or an alcohol derivative.
  • the alkoxy group preferably contains 1 to 8 carbon atoms, more particularly 1 to 4 carbon atoms.
  • M is desirably selected from the group consisting of alkalis, alkali metals and alkaline earth metals for example, sodium or potassium, or ammonium, alkylamine or aminoalcohol .
  • the alkyla ine comprises 8 to 22 carbon atoms, more preferably 10 to 18.
  • the aminoalcohol comprises 1 to 22, preferably 2 to 18 carbon atoms.
  • the surfactant is present from about 0.1% to 40% wt/wt of the composition.
  • compositions may optionally comprise at least one additional surfactant. Additional surfactants which may be used include those used in conventional glyphosate compositions.
  • the invention also relates to a method of controlling weeds, said method comprising applying to the weeds and the locus in which they grow a herbicidally effective amount of a herbicidal composition described above.
  • Another feature of the invention is a method of controlling weeds growing among a crop of glyphosate-resistant genetically engineered plants, comprising applying to the weeds and the crop a herbicidal composition described above. It is known that plants such as sugar beet which have been genetically engineered to be glyphosate-resistant are available.
  • the herbicidal composition may be diluted with water prior to application.
  • the N-acyl sarcosinate surfactants themselves when sprayed on vegetation exhibit no phytotoxicity to the vegetation and in some instances appear to enhance growth.
  • the composition may be diluted to a concentration that is typically sprayed from 100 - 450 g/litre acid equivalent solutions.
  • Glyphosate, and its herbicidally active derivatives, particularly its salts, or mixtures thereof which act as the herbicidally active ingredients of the composition of the present invention can be prepared by a variety of oxidations of phosphonoiminodiacetic acid, (PMIDA), that are well known in the art.
  • PMIDA phosphonoiminodiacetic acid
  • US patent number 3,954,848 discloses the production of glyphosate by the acid catalysed oxidation of PMIDA. Specifically PMIDA is mixed with water and an acid and the mixture is heated to elevated temperatures. An oxidising agent such as hydrogen peroxide is added to convert the PMIDA to glyphosate, which is subsequently isolated by precipitation.
  • US patent 3,969,398 discloses the oxidation of PMIDA to glyphosate employing molecular oxygen in the form of air, oxygen or oxygen diluted with helium, argon, nitrogen or other inert gasses. Activated carbon is employed as a catalyst.
  • US patent 4,147,719 discloses production of certain mono- and di-salts of glyphosate in a single aqueous reaction system by oxidising a salt of PMIDA with a molecular oxygen-containing gas in the presence of platinum supported on an activated carbon substrate. The oxidation reaction is carried out at elevated pressures ranging from 1.5 to 2 5 kg/cm .
  • US patent 4,898,972 discloses the production of glyphosate by the oxidation of PMIDA using cobalt or manganese salts in the presence of bromide.
  • US patent 4,002,672 discloses the production of glyphosate by the acid catalysis of PMIDA. PMIDA is contacted with a strong acid having a pKa of less than 2.2, at an elevated temperature so as to cause the decomposition or hydrolysis of PMIDA to N-phosphonomethyl glycine.
  • US patent 4,696,722 discloses how the activity of a carbon catalyst can be enhanced by first removing the oxides of carbon from the surface. Any of these methods can be used to produce the glyphosate for use in compositions of the present invention.
  • Neutralisation of the glyphosate can be effectuated by any suitable base to form a herbicidally active derivative of glyphosate.
  • suitable bases include alkali metal, alkaline earth metal or ammonium hydroxides and alkyl amines.
  • Preferred glyphosate salts upon neutralisation include the mono(trimethylamine) , mono(diethylenetriamine) , mono n-propylamine, mono isopropyl amine, mono sodium salt or mono potassium salt of N-phosphonomethyl glycine.
  • Those skilled in the art will appreciate that the corresponding di and tri salts of N-phosphonomethyl glycine can be prepared by an appropriate increase to the amount of base added on neutralisation.
  • Certain surfactants are known to act in glyphosate formulations as activators that increase the biological activity of glyphosate.
  • Ethoxylated amines are considered by those skilled in the art to be the most effective surfactants which may be employed in glyphosate solutions (c.f. Wyril and Burnside referenced above).
  • Wyril and Burnside concluded in the reference given that the effectiveness of amine-containing surfactants increased with corresponding increases in the hydroph ⁇ e-lypophile balance (HLB) and the degree of ethoxylation of the surfactant.
  • HLB hydroph ⁇ e-lypophile balance
  • commercially formulated glyphosate compositions contain alkyl amine ethoxylates, and in particular, tallow amine ethoxylates.
  • the amount of surfactant added is from about 0.1% to 20%, (wt/wt), of the formulation with the actual amount depending on the particular surfactant employed.
  • the activating surfactants for use in the present invention are N-acyl sarcosinates having the following general formula:
  • R preferably represents an alkyl or alkenyl group having from 1 to 40 carbon atoms, preferably 8 to 22 carbon atoms and more preferably 10 to 18 carbon atoms, and M is H or a positively charged ion. M functions as a counterion to balance the negative charge on the other part of the molecule.
  • the surfactant N-acyl sarcosinate
  • the N-acyl sarcosinate can be added to a glyphosate or glyphosate salt solution. Subsequent adjustment of the pH with a suitable base such as isopropyl amine can be conducted. .
  • a suitable base such as isopropyl amine
  • the surfactant and a suitable base such as isopropylamine can be admixed prior to addition to the glyphosate solution.
  • Concentrated liquid compositions can be prepared by simple mixing operations. However it will also be obvious to those familiar with the art that solid powder or granular formulations can also be prepared by simple mixing of glyphosate or an active derivative of glyphosate or mixtures of glyphosate and/or mixtures of active derivatives of glyphosate with a solid surfactant.
  • compositions according to the present invention can contain other components, in particular one or more other surfactants, formulation agents, anti -foams, corrosion inhibitors, sequesterants, penetrating agents, antifreezes and adhesives.
  • Oleoyl sarcosinate isopropyl amine salt under agitation. 34.00g of water was charged under agitation and the solution was found to be clear and stable.
  • the solution from example 4 was diluted to 1% glyphosate acid equivalent solution. This was done to get approximately the same concentrations as in commercially available glyphosate formulations (i.e. 0.1 kg of glyphosate acid was applied per acre) and sprayed on four 20X10 ft plots of mixed broad leaf weeds and grasses to evaluate the performance of the herbicide.
  • a commercial formulation available from Monsanto Inc. under the trade mark Round Up and also containing glyphosate as an active herbicidal ingredient at a concentration of 360g per litre acid equivalent was similarly diluted to the same active concentration and sprayed on another 20X10 ft plot.
  • the percentage overall kill is given in Table II. The overall kill was judged visually by the browning or burn demonstrated by the grass/weeds of each plot.
  • test results showed that a single instillation of the test material to the non-irrigated eyes of three rabbits produced minimal to moderate conjunctiva! irritation. All treated eyes appeared normal on observation 24 hours after instillation.
  • the test material produced a maximum score of 5.3 and was classified as a minimal irritant, (class 3 on a 1 to 8 scale), to the rabbit eye according to a modified Kay and Calandra classification system. As a result, the material did not meet the criteria for classification as an irritant according to EU classification regulations. The material does not therefore have to be labelled as an irritant. No symbol and risk phases are required on labels for the test material and no irritancy label.
  • the 50% (w/v) aqueous dilution of the test material produced a maximum total score of 23.0 after 3 hours and was considered to be at a least moderate irritant, (Class 5 on a 1 to 8 scale) to the rabbit eye according to a modified Kay and Calandra classification system.

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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

La présente invention concerne des compositions herbicides comprenant d'une part de la N-phosphonométhyle-glycine, et/ou l'un au moins de ses dérivés actifs comme herbicide, et d'autre part un agent tensio-actif à base d'un N-acyle-sarcosinate. Ces compositions s'avèrent être nettement moins irritantes pour les yeux de l'utilisateur, tout en conservant leur efficacité herbicide.
PCT/IE1998/000086 1997-10-24 1998-10-23 Composition herbicide comprenant du glyphosate et un n-acyle-sarcosinate WO1999021423A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU96418/98A AU9641898A (en) 1997-10-24 1998-10-23 A herbicidal composition comprising glyphosate and an n-acylsarcosinate
EP98950276A EP1024699A1 (fr) 1997-10-24 1998-10-23 Composition herbicide comprenant du glyphosate et un n-acyle-sarcosinate

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IES970766 IES970766A2 (en) 1997-10-24 1997-10-24 A herbicidal composition comprising glyphosate (N-phosphonomethyl glycine) and an N-acyl sarcosinate
IES970766 1997-10-24

Publications (1)

Publication Number Publication Date
WO1999021423A1 true WO1999021423A1 (fr) 1999-05-06

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Family Applications (2)

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PCT/IE1998/000087 WO1999021424A1 (fr) 1997-10-24 1998-10-23 Composition herbicide comprenant du glyphosate (n-phosphonomethyle glycine) et un n-acyle-sarcosinate
PCT/IE1998/000086 WO1999021423A1 (fr) 1997-10-24 1998-10-23 Composition herbicide comprenant du glyphosate et un n-acyle-sarcosinate

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PCT/IE1998/000087 WO1999021424A1 (fr) 1997-10-24 1998-10-23 Composition herbicide comprenant du glyphosate (n-phosphonomethyle glycine) et un n-acyle-sarcosinate

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Country Link
EP (1) EP1024699A1 (fr)
AU (2) AU9557398A (fr)
IE (1) IES970766A2 (fr)
WO (2) WO1999021424A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001017358A1 (fr) * 1999-09-09 2001-03-15 Monsanto Technology Llc. Procede ameliore permettant d'eliminer les mauvaises herbes au moyen de l'herbicide glyphosate
EP1083793A1 (fr) * 1998-06-04 2001-03-21 Hampshire Chemical Corporation N-acyle-sarcosinates utilises comme adjuvants du glyphosate
EP1220610A1 (fr) * 1999-10-13 2002-07-10 Nufarm Limited Composition herbicide et adjuvant
US6746976B1 (en) 1999-09-24 2004-06-08 The Procter & Gamble Company Thin until wet structures for acquiring aqueous fluids

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AUPR682201A0 (en) * 2001-08-03 2001-08-30 Nufarm Limited Glyphosate composition
WO2006023431A2 (fr) 2004-08-19 2006-03-02 Monsanto Technology Llc Composition herbicide a base de sels de glyphosate
US8236731B2 (en) 2005-05-24 2012-08-07 Monsanto Technology Llc Herbicide compatibility improvement
US8987172B2 (en) 2009-06-14 2015-03-24 Pedro Manuel Brito da Silva Correia Herbicide containing glyphosate and a surfactant consisting essentially of a polyalkoxylated alkylamine wherein the alkyl group is branched

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996020593A1 (fr) * 1994-12-30 1996-07-11 Hampshire Chemical Corp. Compositions herbicides contenant du glyphosate, un agent tensioactif d'activation et de l'uree, du polyurethanne ou du polyuree-urethanne
WO1997003560A1 (fr) * 1995-07-19 1997-02-06 Hampshire Chemical Corp. Sarcosinates utilises comme adjuvants et activateurs de fluazifop-p-butyle

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996020593A1 (fr) * 1994-12-30 1996-07-11 Hampshire Chemical Corp. Compositions herbicides contenant du glyphosate, un agent tensioactif d'activation et de l'uree, du polyurethanne ou du polyuree-urethanne
WO1997003560A1 (fr) * 1995-07-19 1997-02-06 Hampshire Chemical Corp. Sarcosinates utilises comme adjuvants et activateurs de fluazifop-p-butyle

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
"Abstr. Pap. Am. Chem. Soc., 211 Meet., AGRO 194", 1996, AMERICAN CHEMICAL SOCIETY *
DATABASE CROPU CRUDDEN J.J.: "N-acyl sarcosinates: effective, ecofriendly adjuvants for pesticide formulation.", XP002092366 *

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1083793A1 (fr) * 1998-06-04 2001-03-21 Hampshire Chemical Corporation N-acyle-sarcosinates utilises comme adjuvants du glyphosate
EP1083793A4 (fr) * 1998-06-04 2002-04-03 Hampshire Chemical Corp N-acyle-sarcosinates utilises comme adjuvants du glyphosate
WO2001017358A1 (fr) * 1999-09-09 2001-03-15 Monsanto Technology Llc. Procede ameliore permettant d'eliminer les mauvaises herbes au moyen de l'herbicide glyphosate
JP2003528033A (ja) * 1999-09-09 2003-09-24 モンサント テクノロジー エルエルシー グリホサート除草剤で雑草を枯らす増強された方法
AU766395B2 (en) * 1999-09-09 2003-10-16 Monsanto Technology Llc Enhanced method of killing weeds with glyphosate herbicide
US6908882B1 (en) * 1999-09-09 2005-06-21 Monsanto Company Enhanced method of killing weeds with glyphosate herbicide
US6746976B1 (en) 1999-09-24 2004-06-08 The Procter & Gamble Company Thin until wet structures for acquiring aqueous fluids
EP1220610A1 (fr) * 1999-10-13 2002-07-10 Nufarm Limited Composition herbicide et adjuvant
EP1220610A4 (fr) * 1999-10-13 2003-01-22 Nufarm Ltd Composition herbicide et adjuvant

Also Published As

Publication number Publication date
AU9557398A (en) 1999-05-17
EP1024699A1 (fr) 2000-08-09
IES970766A2 (en) 1999-05-05
AU9641898A (en) 1999-05-17
WO1999021424A1 (fr) 1999-05-06

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