WO2000008927A1 - Phytosanitary formulations with high active substance content - Google Patents
Phytosanitary formulations with high active substance content Download PDFInfo
- Publication number
- WO2000008927A1 WO2000008927A1 PCT/FR1999/001977 FR9901977W WO0008927A1 WO 2000008927 A1 WO2000008927 A1 WO 2000008927A1 FR 9901977 W FR9901977 W FR 9901977W WO 0008927 A1 WO0008927 A1 WO 0008927A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- formulation according
- radical
- represent
- formula
- average
- 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 phytosanitary formulations, more particularly comprising a liquid, comprising high contents of active material.
- phytosanitary active ingredients at the sites to be treated is generally carried out by spraying corresponding fluid solutions or dispersions.
- fluid solutions or dispersions are aqueous solutions or dispersions or in oragnic solvents, wettable powders or dispersible granules.
- At least one surfactant and / or another compound is generally present in order to promote the solubilization and / or to reinforce the biological activity of the active ingredient considered.
- Glyphosate is a widely used aminophosphate herbicide and its commercial formulations advantageously incorporate an ethoxylated amine.
- Another objective of formulators is also to develop formulations that are as concentrated as possible in active matter. However, the higher the concentration of active material, the more difficulties are encountered in stabilizing the resulting formulations.
- One of the objects of the present invention is therefore to propose phytosanitary formulations combining the double advantage mentioned above, namely low toxicity and high concentration.
- the subject of the present invention is phytosanitary formulations whose content of water-soluble active material is greater than 450 g / l, comprising a mixture of the following compounds:
- R 1 represents a C4-C12 hydrocarbon radical, linear or not, saturated or unsaturated
- R 2 which may or may not be identical from one group to another, represent a hydrogen atom or a methyl or ethyl radical, n is an average number of units between 2 and 10,
- M which may or may not be identical, represent a hydrogen atom, an alkaline, alkaline-earth metal, an N (R3) + radical for which the R3 radicals, identical or different, represent a hydrogen atom or a hydrocarbon radical in Ci-C ⁇ , linear or not, saturated or unsaturated, optionally substituted by a hydroxyl group, or else a radical of type RO (CH2CHR'-O) m -; formula in which R represents a C4-C-12 hydrocarbon radical, linear or not, saturated or unsaturated; R ′, which may or may not be identical from one group to another, represent a hydrogen atom or a methyl or ethyl radical, and m is an average number of units between 2 and 10;
- R 4 identical or different, represent a C2-C22 hydrocarbon group, alkyl or alkenyl, linear or branched, cycloalkyl or alkylaryl,
- R5 identical or different, represent hydrogen or a C1-C4 alkyl radical
- the phytosanitary formulations according to the invention comprise a high content of active material.
- the content of active material is greater than 450 g / l. More particularly, it is greater than or equal to 490 g / l.
- the formulations according to the invention can contain up to 520 g / l, or even up to 540 g / l in active material, and remain stable under cold storage conditions (0 ° C.) or at higher temperature (54 ° C).
- the active materials capable of entering into the composition of the formulations according to the invention are preferably water-soluble.
- phytosanitary active material is intended to denote, according to the invention, pesticides such as insecticides, herbicides, fungicides, but also nutrients promoting the growth and development of plants. They are preferably herbicides.
- aminophosphate derivatives or aminophosphonates
- glyphosate glyphosate, sutphosate, glufosinate
- organic or inorganic salts of these compounds e.g. glyphosate, sutphosate, glufosinate
- the formulations according to the invention comprise glyphosate, and more particularly glyphosate in the form of salt.
- glyphosate is meant more particularly N-phosphonomethylglycine as well as any derivative thereof leading in aqueous solution to glyphosate anions.
- ammonium salts such as sodium or potassium
- ammonium salts type N (R) 4 + for which radicals R, which are identical or different, represent a hydrogen atom or a linear or unsaturated, saturated or unsaturated hydrocarbon radical, optionally substituted by a hydroxyl group
- the sulfonium salts said salts being present alone or in combination.
- ammonium salts that may be mentioned very particularly, secondary or primary amines such as isopropylamine, dimethylamine or diamines such as ethylenediamine.
- sulfonium salts trimethylsulfonium is perfectly suitable.
- the nutrients it is preferably metallic salts such as zinc and iron, for example, and preferably manganese. These salts are used in the form of E.D.T.A. chelates. for example or sulfates.
- E.D.T.A. chelates for example or sulfates.
- the compound of type [a] represents at least one polyalkoxylated phosphate ester of average formula (I):
- R 1 represents a hydrocarbon radical, linear or not, saturated or unsaturated, of C4-C12,
- R 2 which may or may not be identical from one group to another, represent a hydrogen atom or a methyl or ethyl radical, n is an average number of units between 2 and 10,
- M which may or may not be identical, represent a hydrogen atom, an alkaline, alkaline-earth metal, a radical of type N (R) 4 + for which the radicals R3, identical or different, represent a hydrogen atom or a radical hydrocarbon C ⁇ -CQ, linear or not, saturated or not, optionally substituted by a hydroxyl group, or a radical of type RO (CH2CHR'-O) m -; formula in which R represents a C4-C-12 hydrocarbon radical, linear or not, saturated or unsaturated; R ', which may or may not be identical from one group to another, represent a hydrogen atom or a methyl or ethyl radical, and m is an average whole number of units between 2 and 10.
- the compound of formula (I) is in the form of at least one polyalkoxylated phosphate monoester, a polyalkoxylated phosphate diester, or a mixture of these two esters. More particularly, the polyalkoxylated phosphate ester of formula (I) is such that the radical R 1 is an alkyl radical in C4-C ⁇ 2 -
- the radical R 2 represents a hydrogen atom.
- a preferred variant consists of compounds of formula (I) for which M, which may or may not be identical, represent a hydrogen atom, an alkali metal, preferably sodium, or alternatively a group of type N (R3) 4 + for which the radicals R 3 , identical or different, represent a hydrogen atom or, more preferably, a hydrocarbon radical in As an appropriate radical R3, mention may be made of the isopropyl radical.
- a compound of several compounds of formula (I) is used, as compound [a], for which, on average, R 1 , R2, M and n meet the conditions set out above.
- the compound [b] entering into the composition of the phytosanitary formulations according to the invention corresponds to at least one polyalkoxylated amidoamine of average formula (II) or (III):
- R4 identical or different, represent a C 2 -C 2 2 hydrocarbon group > alkyl or alkenyl, linear or branched, cycloalkyl or alkylaryl,
- R5 identical or different, represent hydrogen or a C1-C4 alkyl radical
- - p, q, r, s and t identical or different, represent average numbers of units, which may be zero, with p + q between 1 and 20 and r + s + t between 1 and 20;
- the phytosanitary composition comprises an effective amount of a mixture of polyalkoxylated amidoamines of average formula (II) and (III).
- the radical R2 represents hydrogen or a methyl radical
- a particular embodiment of the invention consists of polyaicoxylated amidoamines in which the coefficients p, q, r, s and t, which are identical or different, are such that the sum of p and q on the one hand, and the sum of r, s and t on the other hand, are each between 2 and 20, more particularly between 3 and 15, preferably between 4 and 7
- polyaoxoxylated amidoamines As particularly suitable polyaoxoxylated amidoamines, mention may be made of polyethoxylated hydroxyethylcocoylamidoamines comprising on average 4 to 7 ethylene oxide units, corresponding to formula (II) and / or (III). According to a preferred embodiment of the invention, such amidoamines are used as a mixture.
- polyaicoxylated amidoamines of formula (II) and (III) can be prepared for example by polycondensation of alkylene oxide on an amidoamine of formulas (IV) or (V) or a mixture of amidoamines of formulas (IV) and ( V)
- This operation can be carried out at a temperature of the order of 70 to 180 ° C, preferably of the order of 110 to 150 ° C, by continuous addition of the activated derivative of alkylene glycol in a proportion of the on the order of 1 to 50 molar equivalents of alkylene oxide relative to the amidoamines of formula (IV) and (V), more particularly on the order of 1, 1 to 25 molar equivalents Preferably, this proportion is order of 2 to 20 molar equivalents
- This operation can also be carried out in the presence of a third solvent.
- a solvent By way of example of a solvent, mention may be made of saturated aliphatic hydrocarbons, such as heptane or octane, aromatic hydrocarbons, such as toluene, cumene, ketones such as in particular octanone-2, secondary alcohols or tertiary, such as isopropanol, tert-butanol, and water
- This catalyst can be acid, preferably of the acid type of Lewis, such as for example boron t ⁇ fluoride, tin tetrachloride, antimony pentachloride
- a basic catalyst chosen in particular from alkali metal hydroxides, such as NaOH, KOH, alkali or alkaline earth metal alcoholates, such as sodium methylate or potassium tert-butoxide.
- catalysts of rare earth derivatives, such as in particular phosphates, carbonates, lanthanum oxides. If a catalyst is used, the quantities used correspond to approximately 0.05 to 10%, preferably approximately 0.1 to 1% by weight relative to the reaction mass.
- the compounds [a] and [b] present in the phytosanitary formulations according to the invention can be found in association, that is to say present as such. They can also be found as a combination.
- this term is meant a form corresponding to the reaction of one on the other. More particularly, the mixture results from the neutralization of the compound [a] by the compound [b].
- the compound [a] is found, before neutralization, in a form in which at least one of the radicals M corresponds to a hydrogen atom.
- formulations according to the invention can simultaneously comprise the associated and combined forms.
- the phytosanitary formulations according to the present invention are such that the weight ratio [a] / [b] is between 80/20 and 20/80, these two limits being excluded. More particularly, said ratio is 80/20 excluded to 40/60. Preferably, the ratio is between 80/20 excluded and 45/55. Note that in the case where the compounds are in combined form, said ratio is calculated from the "isolated" compounds.
- the formulations are such that the weight ratio of [a] / [b] is between 70/30 and 45/55, these two limits being included.
- the weight ratio of the active material to the sum of the compounds [a] and [b] can vary between 1/5 and 15/1, preferably 1/5 to 10/1.
- the weight ratio is understood to be active material expressed in the form of an acid equivalent.
- composition according to the invention may also contain other additives. They may, for example, be antifreeze agents such as glycerol or ethylene glycol, dyes, anti-foaming agents and / or surfactants. It can also contain an effective amount of at least one other phytosanitary active ingredient. It may in particular be herbicides chosen from simazine, isoxaben, atrazine, diuron, terbuthylazine, norflurazon, metamitron, chloridazon, sulfonyl urea and trifluralin, alone or in combination.
- the composition according to the invention is prepared by simple mixing of the water-soluble phytosanitary active ingredient with the compounds [a] and [b], optionally in the presence of other additives.
- composition according to the invention can be prepared well before its use but also just before it.
- the compounds [a] and [b] are added to the phytosanitary active ingredient, possibly to the other additives, during the dilution of the formulation in the spray tank (tank mix).
- the formulations according to the invention can be applied as an insecticide, herbicide, fungicide or fertilizer.
- the compounds [a] and [b] as they have been defined are effective biological activators, and this, whatever the form of the phytosanitary composition (solid, liquid).
- a formulation is prepared, the glyphosate concentration of which is 490 g / l expressed in acid equivalent, by mixing, with stirring, the following compounds:
- the amidoamine used corresponds to a mixture of polyethoxylated hydroxyethyl cocoylamidoamines comprising 4.2 moles of ethylene oxide on average.
- Geronol CF / AR (marketed by the company Rhodia Geronazzo) is a mixture of mono- and di-ester phosphates of formula (I) derived from aliphatic alcohols saturated with C4-C10, and comprising on average 3 to 8 ethylene oxide units, and M is isopropyl ammonium.
- a formulation is prepared, the glyphosate concentration of which is 490 g / l expressed in acid equivalent, by mixing, with stirring, the following compounds:
- the amidoamine used corresponds to a mixture of polyethoxylated hydroxyethyl cocoylamidoamines comprising 6.8 moles of ethylene oxide on average.
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 (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA002340022A CA2340022A1 (en) | 1998-08-12 | 1999-08-12 | Phytosanitary formulations with high active substance content |
EP99936727A EP1104235A1 (en) | 1998-08-12 | 1999-08-12 | Phytosanitary formulations with high active substance content |
BR9912931-0A BR9912931A (en) | 1998-08-12 | 1999-08-12 | Phytosanitary formulation |
AU51719/99A AU749008B2 (en) | 1998-08-12 | 1999-08-12 | Phytosanitary formulations with high active substance content |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9810339A FR2782244B1 (en) | 1998-08-12 | 1998-08-12 | PHYTOSANITARY FORMULATIONS WITH HIGH CONTENT IN ACTIVE MATERIAL |
FR98/10339 | 1998-08-12 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2000008927A1 true WO2000008927A1 (en) | 2000-02-24 |
Family
ID=9529622
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR1999/001977 WO2000008927A1 (en) | 1998-08-12 | 1999-08-12 | Phytosanitary formulations with high active substance content |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP1104235A1 (en) |
AU (1) | AU749008B2 (en) |
BR (1) | BR9912931A (en) |
CA (1) | CA2340022A1 (en) |
FR (1) | FR2782244B1 (en) |
WO (1) | WO2000008927A1 (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2001095720A1 (en) * | 2000-06-15 | 2001-12-20 | Akzo Nobel Nv | Use of amine compounds with improved biodegradability as adjuvants for pesticides and fertilisers |
US6992045B2 (en) | 2000-05-19 | 2006-01-31 | Monsanto Technology Llc | Pesticide compositions containing oxalic acid |
US7135437B2 (en) | 2000-05-19 | 2006-11-14 | Monsanto Technology Llc | Stable liquid pesticide compositions |
ITVA20090040A1 (en) * | 2009-07-01 | 2011-01-02 | Lamberti Spa | WATER-BASED HERBICIDE CONCENTRATE |
JP2014111616A (en) * | 2007-12-21 | 2014-06-19 | Huntsman Petrochemical Llc | Method of preparing amidoamine alkoxylates and compositions thereof |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2662053A1 (en) * | 1990-05-21 | 1991-11-22 | Rhone Poulenc Agrochimie | HERBICIDE SOLUTIONS BASED ON N-PHOSPHONOMETHYLGLYCIN. |
EP0672346A1 (en) * | 1990-08-09 | 1995-09-20 | Monsanto Company | New surfactant compositions, method for their preparation, and pesticidal compositions containing same |
FR2737390A1 (en) * | 1995-08-04 | 1997-02-07 | Rhone Poulenc Chimie | WATER-SOLUBLE PHYTOSANITARY COMPOSITION CONTAINING AT LEAST POLYACOXYLATED AMIDOAMINES |
-
1998
- 1998-08-12 FR FR9810339A patent/FR2782244B1/en not_active Expired - Fee Related
-
1999
- 1999-08-12 CA CA002340022A patent/CA2340022A1/en not_active Abandoned
- 1999-08-12 AU AU51719/99A patent/AU749008B2/en not_active Ceased
- 1999-08-12 BR BR9912931-0A patent/BR9912931A/en not_active IP Right Cessation
- 1999-08-12 EP EP99936727A patent/EP1104235A1/en not_active Withdrawn
- 1999-08-12 WO PCT/FR1999/001977 patent/WO2000008927A1/en active IP Right Grant
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2662053A1 (en) * | 1990-05-21 | 1991-11-22 | Rhone Poulenc Agrochimie | HERBICIDE SOLUTIONS BASED ON N-PHOSPHONOMETHYLGLYCIN. |
EP0672346A1 (en) * | 1990-08-09 | 1995-09-20 | Monsanto Company | New surfactant compositions, method for their preparation, and pesticidal compositions containing same |
FR2737390A1 (en) * | 1995-08-04 | 1997-02-07 | Rhone Poulenc Chimie | WATER-SOLUBLE PHYTOSANITARY COMPOSITION CONTAINING AT LEAST POLYACOXYLATED AMIDOAMINES |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6992045B2 (en) | 2000-05-19 | 2006-01-31 | Monsanto Technology Llc | Pesticide compositions containing oxalic acid |
US7135437B2 (en) | 2000-05-19 | 2006-11-14 | Monsanto Technology Llc | Stable liquid pesticide compositions |
US7723265B2 (en) | 2000-05-19 | 2010-05-25 | Monsanto Technology | Pesticide compositions containing oxalic acid |
WO2001095720A1 (en) * | 2000-06-15 | 2001-12-20 | Akzo Nobel Nv | Use of amine compounds with improved biodegradability as adjuvants for pesticides and fertilisers |
US6747164B2 (en) | 2000-06-15 | 2004-06-08 | Akzo Nobel N.V. | Use of amine compounds with improved biodegradability as adjuvants for pesticides and fertilizers |
KR100787071B1 (en) | 2000-06-15 | 2007-12-21 | 악조 노벨 엔.브이. | Use of amine compounds with improved biodegradability as adjuvants for pesticides and fertilisers |
JP2014111616A (en) * | 2007-12-21 | 2014-06-19 | Huntsman Petrochemical Llc | Method of preparing amidoamine alkoxylates and compositions thereof |
US20160007595A1 (en) * | 2007-12-21 | 2016-01-14 | Huntsman Petrochemical Llc | Method of Preparing Amidoamine Alkoxylates and Compositions Thereof |
ITVA20090040A1 (en) * | 2009-07-01 | 2011-01-02 | Lamberti Spa | WATER-BASED HERBICIDE CONCENTRATE |
WO2011000880A2 (en) * | 2009-07-01 | 2011-01-06 | Lamberti Spa | Aqueous herbicide concentrate |
WO2011000880A3 (en) * | 2009-07-01 | 2011-07-21 | Lamberti Spa | Aqueous herbicide concentrate |
Also Published As
Publication number | Publication date |
---|---|
FR2782244B1 (en) | 2000-09-15 |
FR2782244A1 (en) | 2000-02-18 |
AU5171999A (en) | 2000-03-06 |
EP1104235A1 (en) | 2001-06-06 |
AU749008B2 (en) | 2002-06-13 |
BR9912931A (en) | 2001-10-09 |
CA2340022A1 (en) | 2000-02-24 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP0869713B1 (en) | Plant protection composition containing one or more water soluble active materials and one or more polyalkoxylated amidoamines | |
CA2019087A1 (en) | Herbicidal compositions based on n-phosphonomethylglycine, and their uses | |
EP2341778B1 (en) | A liquid, homogenous herbicide composition, a method of weed control, a method of production of liquid, homogenous herbicide composition and use of a liquid, homogenous herbicide composition for weed control | |
LU87728A1 (en) | CONCENTRATED LIQUID COMPOSITIONS BASED ON N-PHOSPHONOMETHYLGLYCIN | |
EA011651B1 (en) | Liquid aqueous formulation for crop protection, process for producing thereof and method for controlling unwanted plant growth | |
LU87936A1 (en) | N-PHOSPHONOMETHYLGLYCIN-BASED HERBICIDE SOLUTIONS | |
EP2480070B1 (en) | Monoalkyl sulfosuccinates in pesticide formulations and applications as hydrotropes | |
WO2000008927A1 (en) | Phytosanitary formulations with high active substance content | |
JP2000502673A (en) | Herbicidal composition | |
EP0569264B1 (en) | Water soluble pesticidal composition containing a semi-sulfosuccinate derivative | |
EP1024699A1 (en) | A herbicidal composition comprising glyphosate and an n-acylsarcosinate | |
UA45328C2 (en) | OIL-IN-WATER EMULSION | |
US5198431A (en) | Concentrated aqueous emulsions of neophanes and azaneophanes for use in plant protection | |
FR2661315A2 (en) | Concentrated liquid compositions based on N-phosphonomethylglycine | |
JPH0789810A (en) | Highly concentrated emulsion of neofan and azaneofan for being used in plant protection | |
FR2648317A1 (en) | Concentrated liquid compositions based on N-phosphonomethyl-glycine | |
FR2650157A1 (en) | INSECTICIDE COMPOSITIONS COMPRISING GLUFOSINATE OR ONE OF ITS SALTS AS THE ACTIVE INGREDIENT | |
FR2647306A1 (en) | Concentrated liquid compositions based on N-phosphonomethylglycine | |
CN86103772A (en) | Based on-composition and the use thereof of the stabilisation liquid herbicide of bis-amino formate ester | |
ITMI990087A1 (en) | PLANT HEALTH COMPOSITION IN PARTICULAR LOW FOAM |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): AE AL AM AT AU AZ BA BB BG BR BY CA CH CN CU CZ DE DK 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 MD MG MK MN MW MX NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT 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 SD SL SZ 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) | ||
ENP | Entry into the national phase |
Ref document number: 2340022 Country of ref document: CA Ref country code: CA Ref document number: 2340022 Kind code of ref document: A Format of ref document f/p: F |
|
WWE | Wipo information: entry into national phase |
Ref document number: 1999936727 Country of ref document: EP |
|
WWE | Wipo information: entry into national phase |
Ref document number: 51719/99 Country of ref document: AU |
|
WWE | Wipo information: entry into national phase |
Ref document number: 09762650 Country of ref document: US |
|
WWP | Wipo information: published in national office |
Ref document number: 1999936727 Country of ref document: EP |
|
REG | Reference to national code |
Ref country code: DE Ref legal event code: 8642 |
|
WWW | Wipo information: withdrawn in national office |
Ref document number: 1999936727 Country of ref document: EP |
|
WWG | Wipo information: grant in national office |
Ref document number: 51719/99 Country of ref document: AU |