GB2233229A - Concentrated herbicidal compositions based on N-phosphonomethylglycine - Google Patents
Concentrated herbicidal compositions based on N-phosphonomethylglycine Download PDFInfo
- Publication number
- GB2233229A GB2233229A GB9013692A GB9013692A GB2233229A GB 2233229 A GB2233229 A GB 2233229A GB 9013692 A GB9013692 A GB 9013692A GB 9013692 A GB9013692 A GB 9013692A GB 2233229 A GB2233229 A GB 2233229A
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- United Kingdom
- Prior art keywords
- composition according
- glyphosate
- derivatives
- nature
- surfactant
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 54
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 title claims abstract description 47
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 20
- 239000005562 Glyphosate Substances 0.000 claims abstract description 39
- 229940097068 glyphosate Drugs 0.000 claims abstract description 39
- 239000004094 surface-active agent Substances 0.000 claims abstract description 35
- 239000004009 herbicide Substances 0.000 claims abstract description 12
- 239000007788 liquid Substances 0.000 claims abstract description 6
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 3
- 239000007864 aqueous solution Substances 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 2
- 239000001257 hydrogen Substances 0.000 claims abstract 2
- 239000013543 active substance Substances 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000000243 solution Substances 0.000 claims description 7
- NUFNQYOELLVIPL-UHFFFAOYSA-N acifluorfen Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 NUFNQYOELLVIPL-UHFFFAOYSA-N 0.000 claims description 6
- 150000003863 ammonium salts Chemical class 0.000 claims description 6
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical class O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 claims description 4
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000002890 Aclonifen Substances 0.000 claims description 4
- 239000005507 Diflufenican Substances 0.000 claims description 4
- 239000005510 Diuron Substances 0.000 claims description 4
- 241000196324 Embryophyta Species 0.000 claims description 4
- 239000005588 Oxadiazon Substances 0.000 claims description 4
- CHNUNORXWHYHNE-UHFFFAOYSA-N Oxadiazon Chemical compound C1=C(Cl)C(OC(C)C)=CC(N2C(OC(=N2)C(C)(C)C)=O)=C1Cl CHNUNORXWHYHNE-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
- DDBMQDADIHOWIC-UHFFFAOYSA-N aclonifen Chemical compound C1=C([N+]([O-])=O)C(N)=C(Cl)C(OC=2C=CC=CC=2)=C1 DDBMQDADIHOWIC-UHFFFAOYSA-N 0.000 claims description 4
- 230000003213 activating effect Effects 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- VGPYEHKOIGNJKV-UHFFFAOYSA-N asulam Chemical compound COC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 VGPYEHKOIGNJKV-UHFFFAOYSA-N 0.000 claims description 4
- WYEHFWKAOXOVJD-UHFFFAOYSA-N diflufenican Chemical compound FC1=CC(F)=CC=C1NC(=O)C1=CC=CN=C1OC1=CC=CC(C(F)(F)F)=C1 WYEHFWKAOXOVJD-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 159000000000 sodium salts Chemical class 0.000 claims description 4
- 238000005507 spraying Methods 0.000 claims description 4
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 4
- 238000009736 wetting Methods 0.000 claims description 4
- 239000005484 Bifenox Substances 0.000 claims description 3
- SUSRORUBZHMPCO-UHFFFAOYSA-N MC-4379 Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 SUSRORUBZHMPCO-UHFFFAOYSA-N 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 2
- UWHURBUBIHUHSU-UHFFFAOYSA-N 2-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoylsulfamoyl]benzoic acid Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 UWHURBUBIHUHSU-UHFFFAOYSA-N 0.000 claims description 2
- CABMTIJINOIHOD-UHFFFAOYSA-N 2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]quinoline-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC2=CC=CC=C2C=C1C(O)=O CABMTIJINOIHOD-UHFFFAOYSA-N 0.000 claims description 2
- CHZCERSEMVWNHL-UHFFFAOYSA-N 2-hydroxybenzonitrile Chemical compound OC1=CC=CC=C1C#N CHZCERSEMVWNHL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005496 Chlorsulfuron Substances 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- 239000005981 Imazaquin Substances 0.000 claims description 2
- 229910002651 NO3 Inorganic materials 0.000 claims description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 2
- 239000000853 adhesive Substances 0.000 claims description 2
- 230000001070 adhesive effect Effects 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- VJYIFXVZLXQVHO-UHFFFAOYSA-N chlorsulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)Cl)=N1 VJYIFXVZLXQVHO-UHFFFAOYSA-N 0.000 claims description 2
- 238000005260 corrosion Methods 0.000 claims description 2
- 230000007797 corrosion Effects 0.000 claims description 2
- 239000006260 foam Substances 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 239000005556 hormone Substances 0.000 claims description 2
- 229940088597 hormone Drugs 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- NRXQIUSYPAHGNM-UHFFFAOYSA-N ioxynil Chemical compound OC1=C(I)C=C(C#N)C=C1I NRXQIUSYPAHGNM-UHFFFAOYSA-N 0.000 claims description 2
- 230000000149 penetrating effect Effects 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000003381 stabilizer Substances 0.000 claims description 2
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 claims description 2
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical compound OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims description 2
- 150000003918 triazines Chemical class 0.000 claims description 2
- 239000002794 2,4-DB Substances 0.000 claims 1
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 claims 1
- UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 claims 1
- 101000742062 Bos taurus Protein phosphatase 1G Proteins 0.000 claims 1
- 239000005489 Bromoxynil Substances 0.000 claims 1
- 239000003352 sequestering agent Substances 0.000 claims 1
- 239000012190 activator Substances 0.000 abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 238000010348 incorporation Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 description 10
- 239000012141 concentrate Substances 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- -1 ammonium sulphate Chemical class 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical class CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 4
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 3
- 239000001166 ammonium sulphate Substances 0.000 description 3
- 235000011130 ammonium sulphate Nutrition 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 240000006995 Abutilon theophrasti Species 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 240000001549 Ipomoea eriocarpa Species 0.000 description 1
- 235000005146 Ipomoea eriocarpa Nutrition 0.000 description 1
- 244000234609 Portulaca oleracea Species 0.000 description 1
- 235000001855 Portulaca oleracea Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical class NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
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
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
- A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
Landscapes
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Dispersion Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Liquid herbicidal compositions which consist of aqueous solutions containing a) N-phosphonomethylglycine (glyphosate; (HO)2 P(O)CH2NHCH2COOH) and/or one of its derivatives in a proportion of at least 40 g/l of glyphosate equivalent, and b) a surfactant of formula <IMAGE> [in which R is a C8-22 linear or branched, alkyl or alkenyl chain; A denotes an alkylene group; n, n' and n'' are integers such that n + n' + n'' is @between 1 and 15; and R<1> is hydrogen or an acyl radical] which has the nature @of a biological activator/herbicide. Incorporation of the above surfactant enables concentrated glyphosphate compositions to be formulated.
Description
0 HERBICIDAL COMPOSITIONS BASED ON N-PHOSPHONOMETHYLGLYCINE is The present
invention relates to new concentrated formulations based on Nphosphonomethylglycine or on compounds containing the Nphosphonomethy1glycyl group.
N-Phosphonomethy1glycine (sometimes called glyphosate). together with analogous compoundsi their herbicidal properties and the formulations which contain themi are described in particular in US Patent 3,799.758. Although many glyphosate derivatives which are water-soluble or insoluble are known, It is in fact very generally preferred to employ the watersoluble derivativesi and this is why it is the Nphosphonomethylglycine salts which have been generally developed or commercialized, especially the isopropylammonium salt.
More recently (European Patent Application No. 290.416), attempts have been made to develop concentrates based on N-phosphonomethy1glycine salts, which may contain N-phosphonomethylglycine in acidic form. but,, in any event# containing this Nphosphonomethylglycine and/or Its derivatives in soluble or solubilized forms, the feature of these concentrates being the presence of an alkoxylated amine of a particular type. This alkoxylated amine must contain not more than 12 alkoxy groups per molecule and it must have the nature of a surface-active agent and it must promote the herbicidal activity 'of the 9 N-phosphonomethy1glycine derivatives. It can be employed in a smaller quantity than the known surfactants of the known N-phosphonomethy1glycine formulations. at least with regard to the production of concentrates intended to be applied in the open air. in the form of dilute slurries, at a rate of 100 to 600 llha. When the N-phosphonomethy1glycine-based compositions are compositions containing an ammonium salt such as ammonium sulphate, the ethoxylated amine used in this Patent 290,416 is, in fact, an ethoxylated amine containing only 2 ethoxy groups per molecule.
An objective of the present invention is to provide concentrated compositions or formulations (also called concentrates) based on N-phosphonomethy1glycine, is and especially based on its water-soluble salts.
Another objective of the present invention is to provide concentrates based on N phosphonomethy1glycine or on Its derivatives giving rise to dilute spraying mixtures which have a good herbicidal activity.
Another objective of the invention is to provide concentrates based on N-phosphonomethy1glycine salts using new types of surface-active agents promoting the biological activity.
Another objective of the Invention Is to provide concentrates based on N-phosphonomethy1glycine salts using surfactants which have a capability for improved solubilization.
Another objective of the invention is to provide concentrates based on Nphosphonomethy1glycine salts using new types of surface-active agents which are compatible in concentrated solutions with certain inorganic salts and especially with ammonium sulphate.
It has now been found that these objectives could be wholly or partially attained by virtue of the compositions according to the invention. In what follows the percentages are percentages by weight unless specifically stated. Furthermore. glyphosate equivalent is the name given to the corresponding quantity of product if all the N- phosphonomethy1glycine derivative was in the form of ordinary Nphosphonomethylglycine.
These compositions are liquid compositions consisting of aqueous solutions containing:
a) N-phosphonomethy1glycine and/or one of its derivatives in a proportion of at least 40 g/1 of glyphosate equivalent, b) a surfactant (having the nature of an activator) of formula (A0)n R' R - N CH2 -CH2 -CH2 -N (A0)n a R1 (A0) a - R1 in which R is a linear or branched, alkyl or alkenyl chain containing from 8 to 22 carbon atoms A denotes an alkylene group, preferably ethylene or propylene n, n' and nll are integers such that n + n' + nll is between 1 and 15, preferably 3 and 12 R' is the hydrogen atom or an acyl radical such as formyl, acetyl or propanoyl (that is to say CH3-CH2-CO).
Naturally, this single surfactant may be replaced by a mixture of surfactants in which, on average. R. n, n' and nu correspond to the definitions given above.
An N-phosphonomethy1glycine derivative means a compound containing the chain sequence -CO-CH2-N-CH2-p=0 (the nitrogen atom having a free valency and the phosphorus atom having two free valencies), preferably a salt, ester or amide, these terms being taken in the broad seneei for example so as to Include the sulphonamides.
The present invention advantageously relates to the concentrated compositions such as described above and additionally relating to one or other of the following features:
a) the N-phosphonomethy1glycine is in a quantity not exceeding the solubility limit in the medium in question, preferably between 60 and 200 g/1 and still more preferably between 90 and 150 g/lr b) the concentrated solution contains an ammonium (NH,) salt such as the nitrate, phosphate, sulphamate. thiocyanate or preferably the sulphate, in a proportion of 50 to 400 g/1, preferably 100 to 300 g/1, c) the concentrated compositions are intended to be diluted by the agriculturists in containers containing water so as to make it possible to spread these diluted spraying mixtures at a rate of 100 to 600 llha. the active substancei for its part, being applied at a rate of 0.125 to 4.5 kg/ha, is d) the weight ratio glyphosate equivalent/surfactant is between 0.6 and 6, preferably between 1 and 3, e) the solvent Is water.
The relatively high quantity of surfactant shown above relates to this surfactant with the nature of a biological activator/herbicide. it being understood that the compositions according to theinvention may additionally contain. as will be 1 explained later, all kinds of other components, and especially surfactants of the most diverse kinds and wetting in nature; these surfactants are then employed in dosages which are much lower than the activator dosage.
The concentrated liquid compositions according to the invention are usually prepared merely by mixing the constituents.
The compositions according to the invention usually contain from 5 to 25 % (preferably from 7 to 20 %) of active substances (herbicides), from 0.5 to 40 % (preferably from 10 to 20 %) of surface-active agent(s) of an activating nature. from 10 to 50 % (preferably from 20,to 30 %) of an ammonium salt is (adjuvant). from 0.1 to 10 % of surface-active agent(s) of a wetting nature, from 0 to 30 % of suitable additives such as foam suppressors, corrosion inhibitors. sequestrantsi stabilizers. penetrating agents or adhesives. The compositions according to the invention mayi of course, also contain all the solid or liquid additives corresponding to the usual techniques of making up a formulation.
According to what has already been said, the concentrated compositions according to the Invention may contain one or more surface-active agents besides the surfactant with an activating nature defined above. The surface-active agent employed may be a wetting agent of ionic or nonionic type or a mixture of such surface-active agents. There may be mentioned, for example, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, substituted phenols (especially alkylphenols or arylphenols)r salts of esters of sulphosuccinic acidst taurine derivatives (especially alkyltaurates), phosphoric esters of ethylene oxide polycondensates with alcohols or phenols. esters of fatty acids and of polyols, and derivatives of the above compounds containing sulphate, sulphonate and phosphate functional groups.
In addition to N-phosphonomethy1glycine and/or its derivatives, the compositions used in the invention may contain other known active substances with herbicidal properties or with plant growth-regulating properties.
As herbicidal substance which may be mixed with the glyphosphate derivatives in the compositions according to the Invention there may be mentioned acifluorfen (or its sodium salt). aclonifen, bifenoxi diflufenican. asulam, triazines (especially simazine and atrazine)i diuron and oxadiazon. herbicides of hormone or phenoxy types. especially 2.4-D, [214-DB]r RUP,, hydroxybenzonitriles (especially bromoxynll and ioxynil). imidazolinones (especially imazaquin and Imazapur) and sulphonylureas (especially chlorsulfuron - 8 and metsulfuron). The above names are standardized names used to denote the herbicides.
In most cases these herbicides are employed In a proportion of 1 to 400 parts by weight per 100 parts of glyphosate or of glyphosate equivalent. By employing the term glyphosate equivalent the calculation of the parts is thus reduced as If all the glyphosate derivatives were in the form of Nphosphonomethylglycine.
More precisely, when herbicidal active substances other than glyphosate are employed and are mixed with glyphosate, the following proportions are generally used for the weight ratio wr: (wr is equal is glyphosate or glyphosate + glyphosate + glyphosate + glyphosate + glyphosate + glyphosate + glyphosate + glyphosate + glyphosate + glyphosate glyphosate to glyphosate equivalentlother acifluorfen: 4/100 diuron or oxadiazon: 2 s wr aclonifen: 1/3:s bifenox: 1/3 s diflufenican: 2:s wr asulam: 114 s phenoxy: 213:s hydroxybenzonitrile: 1!s wr triazine: 1/3 s imidazolinone: sulphonylurea:
W,r Wr:S Wr wr:s wr!s 10016 s herbicide) wr S 91100 4 s 10/3 S 1 20 1 4 10 S 1 4 wr:5 100 is As a general rule, the herbicidal compositions used in the invention usually contain approximately from 0.05 to 95 % of one or more herbicidal active substances, approximately from 1 % to 95 % of one or more liquid carriers and optionally approximately from 0.1 to 50 % of one or more surface-active agents.
Examples of solutions according to the invention and examples of use of these solutions are given below by way of an example given without any limitation being implied. The active substance in these examples is Nphosphonomethy1glycine in the form of isopropylammonium salt.
EXAMPLE 1 - N-Phosphonomethy1glycine in the form of isopropylammonium salt 100 g/1 - Ammonium sulphate 200 g/1 - Surfactant of formula defined below 100 g/1 - Water sufficient quantity for 1 1 The surfactant used in this example was a product of formula (CH2-CHz-0)n H Cia H35- N with n + n 1 + n 11 = 3 is (CH2-CH2-0)n. H CH2 -CH2 -CH2 -N (CH2 -CH2 -0)n., H EXAMPLE 2
N-Phosphonomethyl.glycine, in the form of isopropylammonium salt Ammonium sulphate Surfactant employed in Example 1 Water sufficient quantity for EXAMPLE 3
N-Phosphonomethy1glycine in the form of Isopropylammonium salt Ammonium sulphate Surfactant employed In Example 1 Water sufficient quantity for EXAMPLE 4
N-Phosphonomethy1glycine in the form of Isopropylammonium salt Ammonium sulphate g/1 100 g/1 200 g/1 1 1 g/1 150 g/1 150 g/1 1 1 g/1 300 g/1 Surfactant employed in Example 1 100 g/1 Water sufficient quantity for 1 1 EXAMPLE 5
N-Phosphonomethy1glycine in the form of isopropylammonium salt 100 g/1 Acifluorfen In the form of sodium salt 4.5 g/1 Amonium sulphate 200 g/1 Surfactant of the formula defined above with n + n' + nll = 10 Water sufficient quantity for 1 1 These solutions are diluted in water in a proportion of 2.5 and 5 1 in 300 1 and the spraying mixtures thus obtained are sprayed onto various adventitious plants.
The compositions of Examples 1 to 4. employed in the dosage of 250 9/1 of active substance calculated in the form of N-phosphonomethy1glycine, exhibit an effectiveness on various weeds, especially morning glory. purslane and Indian mallow, which is markedly superior to that of commercial products. and especially of the product marketed under the trademark Round-up and which contains the same active substance In combination with ordinary surface-active agents.
Claims (23)
1. A liquid herbicidal composition which comprises an aqueous solution containing:
a) N-phosphonomethy1glycine and/or one of its derivatives in a proportion of at least 40 g/1 of 5 glyphosate equivalent, and b) a surfactant of formula AO) n R1 R - N CH2-CH2-CH2-N (A0) n 1 R1 (A0) n't R1 in which R is a linear or branched, alkyl or alkenyl chain containing from 8 to 22 carbon atoms A denotes an alkylene group.
is n, n' and nll are integers such that n + n' + nll is from 1 to 15 Each R1, which may be the same or different is hydrogen or an acyl radical.
2. The composition according to claim 1, wherein A 20 is an ethylene or propylene group.
3. The composition according to claim 1 or 2, wherein n + n' + nll is between 3 and 12.
4. The composition according to any one of claims 1 to 3, wherein R1 is a formyl, acetyl or propanoyl radical, preferably acetyl. -
5. The composition according to any one of claims 1 to 4, wherein the Nphosphonomethy1glycine and/or one of its derivatives is in a quantity not exceeding the solubility limit in the medium in question and is from 60 to 200 g/1.
6. The composition according to any one of claims 1 to 5, wherein the Nphosphonomethy1glycine and/or one of its derivatives is in a quantity of from 90 to 150 g/1.
7. The composition according to any one of claims 1 to 6, wherein the concentrated solution contains an ammonium salt such as the nitrate, phosphate, sulphamate, thiocyanate or preferably the sulphate, in a proportion of 50 to 400 g/1.
8. The composition according to any one of claims 1 to 7, wherein the concentrated solution contains an ammonium salt in a proportion of 100 to 300 g/1.
9. The composition according to any one of claims 1 to 8, which is intended to be diluted in water so as to make it possible to spread these diluted spraying mixtures at a rate of 100 to 600 1/ha, the active substance, for its part, being applied at a rate of 0.125 to 4.5 kg/ha.
10. The composition according to one of claims 1 to 9, wherein the weight ratio glyphosate equivalent/surfactant is from 0.6 to-6.
11. The composition according to claim 10, wherein the weight ratio is from 1 to 3.
12. The composition according to any one of claims 1 to 11, wherein the solvent is water.
13. The composition according to any one of claims 1 to 12, which comprises other surfactants of a wetting nature and optionally one or more other additives selected from foam supressors, corrosion inhibitors, sequestrants, stabilizers, penetrating agents or adhesives.
14. The composition according to any one of claims 1 to 13, which comprises from 5 to 25 of herbicidal active substance, from 0.5 to 40 of surfaceactive agent(s) of an activating nature, from 10 to 50 % of an ammonium salt (adjuvant), from 0.1 to 10 % of surfaceactive agent(s) of a wetting nature, and from 0 to 30 of other additives.
15. The composition according to any one of claims 1 to 14, which comprises from 7 to 20 of herbicidal active substance, from 10 to 20 % of surfaceactive agent(s) of an activating nature, and from 20 to 30 % of ammonium salt.
16. The composition according to any one of claims 1 to 15, which comprises at least one other - 15 herbicide in addition to N-phosphonomethy1glycine and/or one of its derivatives.
17. The composition according to claim 16 wherein the other herbicide chosen from the group consisting of: 5 acifluorfen (or its sodium salt), aclonifen, bifenox, diflufenican, asulam, triazines (especially simazine and atrazine), diuron and oxadiazon, herbicides of hormone or phenoxy types, especially 2,4-D, [2,4-DB], MCPP, hydroxybenzonitriles (especially bromoxynil and ioxynil), 10 imidazolinones (especially imazaquin and imazapur) and sulphonylureas (especially chlorsulfuron and metsulfuron).
18. The composition according to claim 17, wherein the said other herbicides are present in the following weight ratio wr:
(wr is equal to glyphosate or glyphosate + glyphosate + glyphosate + glyphosate + glyphosate + glyphosate + glyphosate + glyphosate + 25 glyphosate + glyphosate + glyphosate equivalent/other herbicide) acifluorfen: 4/100 5 wr 5 9/100 diuron or oxadiazon: 2 5 wr:5 4 aclonifen: 1/3 5 wr 5 10/3 bifenox: 1/3 5 wr 5 1 diflufenican: asulam: phenoxy: hydroxybenzonitrile: triazine: imidazolinone:
2 5 wr 5 l/ 4:5 wr 2/3 5 wr 1 5 wr 5 1/3 5 wr 1 5 wr 5 20:5 1:5 4 10:S 1 4 - 16 glyphosate + sulphonylurea: 100/6:5 wr 5 100.
19. The composition according to one of claims 16 to 18, which comprises acifluorfen or its sodium salt.
20. The composition according to claim 1 5 substantially as hereinbefore described.
21. A process for combating weeds, in which a composition according to one of claims 1 to 20 is employed.
22. The process according to claim 21, wherein the said composition is diluted and applied at a rate of 100 to 600 1/ha, the active substance being applied at a rate of 0.125 to 4.5 kg/ha.
23. The process according to claim 21 or 22 substantially as hereinbefore described.
1001 tlh. Pt-t Offire- state House. 66171 High Holborn. London WC1R4TP. Further copies may be obtained from Th,Eatent Office.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8908433A FR2648316A1 (en) | 1989-06-20 | 1989-06-20 | HERBICIDE COMPOSITIONS BASED ON N-PHOSPHONOMETHYLGLYCIN AND THEIR USE |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB9013692D0 GB9013692D0 (en) | 1990-08-08 |
| GB2233229A true GB2233229A (en) | 1991-01-09 |
| GB2233229B GB2233229B (en) | 1992-05-06 |
Family
ID=9383094
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9013692A Expired - Lifetime GB2233229B (en) | 1989-06-20 | 1990-06-20 | Herbicidal compositions based on n-phosphonomethylglycine |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPH0334901A (en) |
| KR (1) | KR910000016A (en) |
| AU (1) | AU5756590A (en) |
| BR (1) | BR9002986A (en) |
| CA (1) | CA2019087A1 (en) |
| DE (1) | DE4019362A1 (en) |
| DK (1) | DK149390A (en) |
| FR (1) | FR2648316A1 (en) |
| GB (1) | GB2233229B (en) |
| GR (1) | GR900100459A (en) |
| HU (1) | HUT54023A (en) |
| IE (1) | IE902130A1 (en) |
| IT (1) | IT1248734B (en) |
| LU (1) | LU87747A1 (en) |
| NL (1) | NL9001407A (en) |
| PT (1) | PT94414A (en) |
| SE (1) | SE9002166L (en) |
| ZA (1) | ZA904785B (en) |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994019941A1 (en) * | 1993-03-09 | 1994-09-15 | Kvk Agro A/S | A herbicide preparation, a process for producing it and an activating additive for application therewith |
| WO1995003697A1 (en) * | 1993-07-28 | 1995-02-09 | Kemira Oy | Herbicide composition, activity-promoting agent for improving the efficacy of the herbicide, and a method for treating cultivated plants |
| US6127317A (en) * | 1997-09-17 | 2000-10-03 | American Cyanamid Company | Concentrated, aqueous herbicidal compositions containing an imidazolinyl acid salt and a glyphosate salt |
| US6214768B1 (en) | 1998-09-14 | 2001-04-10 | American Cyanamid Co. | Synergistic herbicidal methods and compositions |
| US6239072B1 (en) * | 1998-03-09 | 2001-05-29 | Monsanto Company | Tank mixtures and premixtures for weed control programs that include postmergence applications of glyphosate plus graminicides in glyphosate tolerant soybeans |
| US6277787B1 (en) | 1998-09-14 | 2001-08-21 | American Cyanamid Co. | Synergistic herbicidal methods and compositions |
| US6420311B1 (en) | 1999-08-18 | 2002-07-16 | Huntsman Petrochemical Corporation | Polyether diamine—based surfactant adjuvants and compositions thereof |
| US6436874B1 (en) | 1998-04-08 | 2002-08-20 | Aventis Cropscience Gmbh | Synergistic herbicidal agents based on leaf herbicides containing phosphorus, imidazolinones and hormone weed killers |
| US6586367B2 (en) | 1996-09-05 | 2003-07-01 | Syngenta Crop Protection, Inc. | Process for the control of weeds |
| US7135437B2 (en) | 2000-05-19 | 2006-11-14 | Monsanto Technology Llc | Stable liquid pesticide compositions |
| WO2011009171A1 (en) * | 2009-07-22 | 2011-01-27 | Huntsman Corporation Australia Pty Limited | Cocoalkylpolyamine alkoxylates as agents for high strength herbicide compositions |
| US8293683B2 (en) | 2006-12-06 | 2012-10-23 | Akzo Nobel N.V. | Alkylamidopropyl dialkylamine surfactants as adjuvants |
| EP1721523A3 (en) * | 2000-05-19 | 2013-01-23 | Monsanto Technology, LLC | Aqueous pesticide formulations and novel surfactants |
| US9012365B2 (en) | 2006-12-06 | 2015-04-21 | Akzo Nobel N.V. | Compatibility agents for herbicidal formulations comprising 2,4-(Dichlorophenoxy) acetic acid salts |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR9606948A (en) * | 1995-02-13 | 1997-12-23 | Novartis Ag Novartis S A Novar | Herbicidal compositions and weed control method |
| FR2737390B1 (en) * | 1995-08-04 | 1997-09-19 | Rhone Poulenc Chimie | WATER-SOLUBLE PHYTOSANITARY COMPOSITION COMPRISING AT LEAST POLYACOXYLATED AMIDOAMINES |
| AUPO405696A0 (en) * | 1996-12-06 | 1997-01-09 | Ici Australia Operations Proprietary Limited | Herbicidal compositions |
| FR2766669B1 (en) * | 1997-07-30 | 1999-10-29 | Flamel Tech Sa | GLYPHOSATE EMULSION, ONE OF ITS PREPARATION METHODS, AND PHYTO-TOXIC COMPOSITION CONTAINING THE SAME |
| NZ502499A (en) * | 1997-07-30 | 2001-11-30 | Monsanto Co | Herbicide consisting of glyphosate composition and polyamine derivatives |
| TW471950B (en) * | 1997-09-17 | 2002-01-11 | American Cyanamid Co | Concentrated, aqueous herbicidal compositions containing an imidazolinyl acid salt and a glyphosate salt |
| DE19836684A1 (en) * | 1998-08-13 | 2000-02-17 | Hoechst Schering Agrevo Gmbh | Use of a synergistic herbicidal combination including a glufosinate- or glyphosate-type, imidazolinone or protoporphyrinogen oxidase to control weeds in rice |
| US6992045B2 (en) | 2000-05-19 | 2006-01-31 | Monsanto Technology Llc | Pesticide compositions containing oxalic acid |
| MX245460B (en) * | 2001-05-21 | 2007-04-27 | Monsanto Technology Llc | Pesticide concentrates containing etheramine surfactants. |
| BRPI0210236B8 (en) * | 2001-06-01 | 2019-11-26 | Huntsman Spec Chem Corp | adjuvant and pesticide compositions |
| DE10250551A1 (en) * | 2002-10-30 | 2004-05-19 | Clariant Gmbh | Pesticide formulations containing alkoxylated amines |
| DE10250552A1 (en) * | 2002-10-30 | 2004-05-19 | Clariant Gmbh | Pesticide formulations containing alkoxylated amines |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0290416A2 (en) * | 1987-04-29 | 1988-11-09 | Monsanto Europe S.A./N.V. | Improved glyphosate formulations |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4528023A (en) * | 1983-07-25 | 1985-07-09 | Stauffer Chemical Company | Enhancement of herbicidal activity of tetraaluminum salts of N-phosphonomethylglycine |
-
1989
- 1989-06-20 FR FR8908433A patent/FR2648316A1/en not_active Withdrawn
-
1990
- 1990-06-13 IE IE213090A patent/IE902130A1/en unknown
- 1990-06-15 CA CA002019087A patent/CA2019087A1/en not_active Abandoned
- 1990-06-18 SE SE9002166A patent/SE9002166L/en not_active Application Discontinuation
- 1990-06-18 DE DE4019362A patent/DE4019362A1/en not_active Withdrawn
- 1990-06-19 PT PT94414A patent/PT94414A/en not_active Application Discontinuation
- 1990-06-19 LU LU87747A patent/LU87747A1/en unknown
- 1990-06-19 DK DK149390A patent/DK149390A/en not_active IP Right Cessation
- 1990-06-19 GR GR900100459A patent/GR900100459A/en unknown
- 1990-06-19 AU AU57565/90A patent/AU5756590A/en not_active Abandoned
- 1990-06-20 JP JP2162548A patent/JPH0334901A/en active Pending
- 1990-06-20 IT IT02070190A patent/IT1248734B/en active IP Right Grant
- 1990-06-20 ZA ZA904785A patent/ZA904785B/en unknown
- 1990-06-20 HU HU903921A patent/HUT54023A/en unknown
- 1990-06-20 BR BR909002986A patent/BR9002986A/en unknown
- 1990-06-20 KR KR1019900009081A patent/KR910000016A/en not_active Withdrawn
- 1990-06-20 NL NL9001407A patent/NL9001407A/en not_active Application Discontinuation
- 1990-06-20 GB GB9013692A patent/GB2233229B/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0290416A2 (en) * | 1987-04-29 | 1988-11-09 | Monsanto Europe S.A./N.V. | Improved glyphosate formulations |
Cited By (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994019941A1 (en) * | 1993-03-09 | 1994-09-15 | Kvk Agro A/S | A herbicide preparation, a process for producing it and an activating additive for application therewith |
| AU685437B2 (en) * | 1993-03-09 | 1998-01-22 | Kvk Agro A/S | A herbicide preparation, a process for producing it and an activating additive for application therewith |
| US5795847A (en) * | 1993-03-09 | 1998-08-18 | Kvk Agro A/S | Herbicide preparation, a process for producing it and an activating additive for application therewith |
| US6180566B1 (en) | 1993-03-09 | 2001-01-30 | Kvk Agro A/S | Herbicide preparation, a process for producing it and an activating additive for application therewith |
| WO1995003697A1 (en) * | 1993-07-28 | 1995-02-09 | Kemira Oy | Herbicide composition, activity-promoting agent for improving the efficacy of the herbicide, and a method for treating cultivated plants |
| US7407913B2 (en) | 1996-09-05 | 2008-08-05 | Syngenta Crop Protection, Inc. | Process for the control of weeds |
| US6586367B2 (en) | 1996-09-05 | 2003-07-01 | Syngenta Crop Protection, Inc. | Process for the control of weeds |
| US6127317A (en) * | 1997-09-17 | 2000-10-03 | American Cyanamid Company | Concentrated, aqueous herbicidal compositions containing an imidazolinyl acid salt and a glyphosate salt |
| US6239072B1 (en) * | 1998-03-09 | 2001-05-29 | Monsanto Company | Tank mixtures and premixtures for weed control programs that include postmergence applications of glyphosate plus graminicides in glyphosate tolerant soybeans |
| US6436874B1 (en) | 1998-04-08 | 2002-08-20 | Aventis Cropscience Gmbh | Synergistic herbicidal agents based on leaf herbicides containing phosphorus, imidazolinones and hormone weed killers |
| US6277787B1 (en) | 1998-09-14 | 2001-08-21 | American Cyanamid Co. | Synergistic herbicidal methods and compositions |
| US6214768B1 (en) | 1998-09-14 | 2001-04-10 | American Cyanamid Co. | Synergistic herbicidal methods and compositions |
| US6420311B1 (en) | 1999-08-18 | 2002-07-16 | Huntsman Petrochemical Corporation | Polyether diamine—based surfactant adjuvants and compositions thereof |
| US7135437B2 (en) | 2000-05-19 | 2006-11-14 | Monsanto Technology Llc | Stable liquid pesticide compositions |
| EP1721523A3 (en) * | 2000-05-19 | 2013-01-23 | Monsanto Technology, LLC | Aqueous pesticide formulations and novel surfactants |
| US8293683B2 (en) | 2006-12-06 | 2012-10-23 | Akzo Nobel N.V. | Alkylamidopropyl dialkylamine surfactants as adjuvants |
| US9012365B2 (en) | 2006-12-06 | 2015-04-21 | Akzo Nobel N.V. | Compatibility agents for herbicidal formulations comprising 2,4-(Dichlorophenoxy) acetic acid salts |
| CN102469778A (en) * | 2009-07-22 | 2012-05-23 | 胡茨曼澳大利亚股份有限公司 | Coco alkyl polyamine alkoxylates as agents for high strength herbicidal compositions |
| WO2011009171A1 (en) * | 2009-07-22 | 2011-01-27 | Huntsman Corporation Australia Pty Limited | Cocoalkylpolyamine alkoxylates as agents for high strength herbicide compositions |
| EP2456302A4 (en) * | 2009-07-22 | 2013-07-24 | Huntsman Corp Australia Pty Ltd | COCOALKYLPOLYAMINE ALCOXYLATES AS ACTIVE AGENTS IN REINFORCED EFFICIENT HERBICIDE COMPOSITIONS |
| AU2010276088B2 (en) * | 2009-07-22 | 2014-10-23 | Indorama Ventures Oxides Australia Pty Limited | Cocoalkylpolyamine alkoxylates as agents for high strength herbicide compositions |
| CN102469778B (en) * | 2009-07-22 | 2015-09-09 | 胡茨曼澳大利亚股份有限公司 | Cocoalkyl polyamines alcoxylates is as the reagent for high strength Herbicidal combinations |
| US9578877B2 (en) | 2009-07-22 | 2017-02-28 | Huntsman Corporation Australia Pty Limited | Cocoalkylpolyamine alkoxylates as agents for high strength herbicide compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| KR910000016A (en) | 1991-01-29 |
| BR9002986A (en) | 1991-08-20 |
| JPH0334901A (en) | 1991-02-14 |
| AU5756590A (en) | 1991-01-03 |
| IT9020701A1 (en) | 1991-12-20 |
| IE902130A1 (en) | 1991-01-02 |
| IT9020701A0 (en) | 1990-06-20 |
| PT94414A (en) | 1991-02-08 |
| GR900100459A (en) | 1991-11-15 |
| ZA904785B (en) | 1991-04-24 |
| DE4019362A1 (en) | 1991-01-03 |
| HUT54023A (en) | 1991-01-28 |
| CA2019087A1 (en) | 1990-12-20 |
| LU87747A1 (en) | 1991-02-18 |
| NL9001407A (en) | 1991-01-16 |
| HU903921D0 (en) | 1990-11-28 |
| GB9013692D0 (en) | 1990-08-08 |
| IE902130L (en) | 1990-12-20 |
| SE9002166L (en) | 1990-12-21 |
| DK149390D0 (en) | 1990-06-19 |
| FR2648316A1 (en) | 1990-12-21 |
| SE9002166D0 (en) | 1990-06-18 |
| DK149390A (en) | 1990-12-21 |
| GB2233229B (en) | 1992-05-06 |
| IT1248734B (en) | 1995-01-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19940620 |