GB2047098A - Herbicidal composition - Google Patents
Herbicidal composition Download PDFInfo
- Publication number
- GB2047098A GB2047098A GB8008670A GB8008670A GB2047098A GB 2047098 A GB2047098 A GB 2047098A GB 8008670 A GB8008670 A GB 8008670A GB 8008670 A GB8008670 A GB 8008670A GB 2047098 A GB2047098 A GB 2047098A
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- United Kingdom
- Prior art keywords
- composition according
- active ingredient
- composition
- active agent
- ammonium
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Classifications
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- 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
- A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
- A01N59/02—Sulfur; Selenium; Tellurium; Compounds thereof
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- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Inorganic Chemistry (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
A herbicidal composition is disclosed which may be used for chemically hoeing fields and cultivated land. This composition contains at least one metal or ammonium salt of persulphuric acid as an active ingredient in association with at least one surface- active agent which is compatible with the active ingredient. The composition according to the invention may be used for chemically hoeing cultivated land which is set out in lines such as orchards, vineyards, nurseries, garden plots and ornamental gardens, the treatment being rapid and involving low remanence of the active ingredient to permit early replanting.
Description
SPECIFICATION
Herbicidal composition
The invention relates to a herbicidai composition which can be used for chemically hoeing fields and cultivated land. The invention also relates to a chemical weeding process of these fields and cultivated land using this composition.
Hoeing is the operation which consists in superficially mellowing the soil by using an appropriate tool such as a hoe or a similar tool to break up the top, superficial layer, a notable result of this being the elimination of any unwanted vegetation. Hoeing is currently performed in the case of cultivated land which is set out in lines, i.e. orchards, vineyards, nurseries, garden plots and ornamental gardens, for example, in order to eliminate the weeds in the areas between the lines of the crop and thus to improve the yield of the crops orto enhance their ornamental effect.
In analogy with the hoeing operation performed by using an appropriate tool, the term "chemical hoeing" is used herein in its convention sense to characterise a treatment of fields and cultivated land which is effected by using a herbicidal composition and which results, as regards the weeds, in the same apparent effect as conventional hoeing, i.e. in the elimination, as rapid and thorough as possible, of the undesirable plants in the treated area.
In order to be able to be used as an active ingredient in the compositions which are intended for chemical hoeing, a herbicidal compound has to meet several well determined conditions:
- it has to exhibit a superior herbicidal activity over the greatest possible number of types of plants, whatever their stage of development from the stage of the seedling up to the stage of the develpped plant;
- its herbicidal action has to be rapid and has to allow the elimination of the particular types of plants, in a time limit of preferably less than 2 weeks, and generally, of a few days.This herbicidal action has to be exercised on the aerial parts of the various plants to be eliminated, excluding any action by the soil because such an action would be likely to be absorbed by the underground parts of the crops in the vicinity of the treated area;
- the herbicidal composition which is used has to exhibit only a very slight remanence in order to avoid any accumulation of the herbicidal product in the soil, where there are repeated treatments and to allow, if necessary, the treated area to be rapidly replanted with crops.
However, although a vast number of herbicidal compounds are known and marketed at present for conventional herbicidal uses, very few of these compounds exhibit all the features required for use as a chemical hoeing agent.
In practice, the only compounds which are conventionally used for this purpose are ethylene-il' dipyridyliylium-4,4' commonly called diquat and dimethyl-1,1 dipyridyliylium- 4,4' commonly called paraquat.
Diquat and paraquat both exhibit superior herbicidal properties and respond in a very satisfactory manner to the different conditons mentioned above. However, there is a disadvantage in that they are very toxic and
thus present considerable risks for those who work with them.
The aim of the present invention is to provide a herbicidal composition, which can be used to hoe chemically fields and cultivated land which meets the various conditions mentioned above concerning this type of use and which also as a very low toxicity so that it can be used without necessitating any special
precautions.
Thus, the present invention provides a herbicidal composition which comprises an effective amount of at least one metal or ammonium salt of persulphuric acid (H2S208) as an active ingredient in association with at least one surface-active agent which is compatible therewith.
The acid of formula H2S208 is sometimes called perdisulphuric acid. In the present context, the term "persulphuric acid" indicates in a general manner the acid of formula H2S208 and "persulphates" indicates the salts of this acid.
French Patent No. 622,405 describes the use of sodium or potassium perborates, persulphates and
peroxides as herbicides to eliminate hardy plants growing between railway lines, on paths, in lanes and roads etc i.e. completely to eliminate the weeds from uncultivated areas, the object being to achieve a total and lasting elimination, over time, of the plants which are present. This use is very different from that according to the present invention wherein a persulphate is used in a composition also including a surface-active agent specifically for chemical hoeing of fields and cultivated land, which treatment requires both a rapid and thorough herbicidal action and a very low remanence of the herbicidal compound, in order to permit the treated areas to be replanted as soon as possible.
The invention particularly relates to compositions comprising a compound of the formula (Me) 2S208, as an active ingredient, wherein Me represents an alkali metal atom or the ammonium radical. These compositions preferably contain ammonium persulphate as the active substance.
As mentioned above, the composition according to the invention must include, besides the active ingredient, at least one surface-active agent which is compatible with the active ingredient. The experiments which we have carried out have shown that, in the absence of a suitable surface-active agent, alkali metal-, alkaline earth metal-or ammonium persulphates exhibit per sea herbicidal activity which is inadequate for use in chemical weeding of fields and cultivated areas, but that it was possible considerably to improve this activity by associating a suitable surface-active agent with the active ingredient.
The same experiments also showed that this improvement in the herbicidal activity was only observed in the case of certain surface-active agents, and that in the case of certain conventional surface-active agents, no improvement in the herbicidal activity was observed and even, in certain other cases, there were results which were considerably lower than those of the alkali metal persulphate or ammonium persulphate used by itself.
The present invention is further illustrated by reference to the following Examples.
EXAMPLE 1
Experiments in the open air on rye grass (Lolium perenne)
The following experiments were carried out on different plots of grass each of 2 m2 in area. For each of
these experiments, a composition was prepared comprising 98% by weight of ammonium persulphate and 2% of a surface-active agent and this composition was then diluted with water in order to obtain a mixture containing 40g/l of ammonium persulphate.
Experiments numbers 1 to 11 were carried out using the following surface-active agents, all or which have a good compatibility with the active ingredient which was used and which resulted in a distinct improvement in its herbicidal activity.
- Experiment No 1-Aerosol OTB (mixture of sodium dioctylsulphosuccinate and sodium benzoate)
- Experiment No 2 - Celanol DOS 75 (sodium dioctylsulphosuccinate)
- Experiment No 3 Cemulsol NP 6 (nonylphenol oxyethylated by six molecules of ethylene oxide)
- Experiment No 4 - Cemulsol 860 C10 oxo-alcohol oxyethylated by six molecules of ethylene oxide)
- Experiment No 5 - Arquad 2C 50 (dimethyl dilauryl ammonium chloride)
- Experiment No 6 - Noranium M2C (dimethyl dialkyl ammonium chloride)
- Experiment No 7 - Hostapon TPHC (sodium salt of oleyl methyl taurine)
- Experiment No 8 - Cemulsol DB 25/18 C16-C18 alcohol oxyethylated by 50 molecules of ethylene oxide)
- Experiment No 9 - Cemulsol BR extra (caster oil oxyethylated by 33 molecules of ethylene oxide)
- Experiment No 10 - Celanol PA 19 (Nonylphenol phosphate acid oxyethylated by 9 moles of ethylene
oxide)
- Experiment No 11 -Supragil WP (sodium isopropyl naphthalene sulphate).
Each of the mixtures obtained in this manner was applied by spraying onto the aerial parts of the plants in a determined plot using a pressure spray fitted with a straight-line-jet nozzle at a pressure of 3 bars, a rate of 0.2 1 of mixture per m2, that is to say a quantity of 89 of ammonium persulphate per m2.
The herbicidal activity, measured by visual observation, in comparison with untreated control plots, was recorded in a scale of from 0 (no herbicidal activity) to 10 (complete herbicidal action) at periods of respectively 1,2 and 6 days after the treatment.
The results which were observed have been recorded in the following tabie, in which the experiment marked "persulphate alone" was carried out by treating a plot with ammonium persulphate, without adding a surface-active agent, in the same quantity as for the other experiments (8 g/m2).
Herbicidal activity
T + 1 day T + 2 days T + 6 days
Persulphate alone
0 4 4 Experiment No 1 5 6 7
Experiment No 2 6 7 8
Experiment No 3 4 5 7
Experiment No 4 5 6 7
Experiment No 5 5 6 8
Experiment No 6 4 5 7 Experiment No 7 4 5 7
Experiment No 8 5 6 7
Experiment No 9 5 6 7
Experiment No 10 4 6 7 Experiment No 11 4 6 7
It will be noted from these results that the compositions which were used in the experiments numbers 1 to 11 exhibited, in each of the samples taken, a herbicidal activity which is clearly superior to that of ammonium persulphate used on its own, in the same quantity per m2.
It will be particularly noted that in the case of these experiments numbers 1 to 11, this herbicidal activity is made evident very rapidly since it is already very significant one day after the time when the chemical hoeing treatment was carried out (activity noted from 4 to 6), while on the same date (T + 1 day), the ammonium persulphate which was used on its own did not show any herbicidal activity (notation) 0).
It has been verified for each of the experiments described above that the surface-active agent which was used on its own in the same quantity/m2 as in these experiments did not exercise any herbicidal activity.
EXAMPLE 2
Experiments in the open air varied plant life
These experiments were carried out on different plots of land, each having an area of 1 m2, in which the following weeds were identified:
- Meadow clover (TrifoliumpratenseL.) - Common sorrel (Rumexacetosa L.)
- Tall crowfoot (Ranunculus acerL.)
- Knot grass (Polygonum aviculare L.) - Greater plantain (Plantago majorL.)
- Wild potentilla (Potentilla reptans L.)
- Feverfew (Matricaria inodora L.)
- Polygonum persicaria (Polygonum persicaria L.)
- Corn mint (Mentha arvensis L.)
- Groundsel (Senecio vulgaris L.)
- Chickweed (Stellaria media)
- Red archangel (Lamiumpurpureum 4.) - Brome grass (Bromus mollis L.)
- Orchard grass (Dactylls glomerata L.) - Dog's tooth grass (Cynodon dactylon (L.) Pers.)
- Rye grass (Lollumperenne L.) - Fescue (Festucapratensis Huds.) - Meadow grass (Poapratensis L.)
In these experiments, numbered 12 and 13, a composition was used containing 98% by weight of ammonium persulphate and 2% of aerosol OTB, a surface-active agent, the chemical composition of which is given in the previous Example. By diluting with water, a mixture of the desired concentration was prepared.
The treatment was carried out according to the method previously described by spraying the mixture onto the aerial parts of the plants which were present in the plots.
The results which were observed and recorded according to the same scale as before are set out in the following table:
Herbicidal Activity
Quantity of T + 2 days T + 6 days
Persulphate
in g/m2 Experiment No 12 10 7 8
Experiment No 13 20 9
It is observed that the herbicidal activity was exercised on all the different weeds quoted above, which indicates the very wide spectrum of herbicidal activity exhibited by the active ingredient used.
EXAMPLE 3
Remanence experiment on the bare soil
This experiment was carried out by treating a mellowed soil, without any vegetation, by using a mixture prepared by diluting the same composition as in Example 2 with water and applying this mixture at the rate of 15 g of ammonium persulphate per m2.
Immediately after the treatment, radishes of the variety "eighteen days", and carrots of the variety "improved and of medium length from Nantes" were sown in the treated plots and in the untreated control
plots.
One month after sowing, it was observed that there was no phytoxicity and moreover that the treated plots exhibited plants with a more developed vegetation than those of the control plots.
These results are explained by the fact that ammonium persuiphate decomposes very rapidly at soil level (i.e. there is very slight remanence) in ammonium sulphate which is a nitrogeneous fertiliser.
The previous Examples show the superior properties of the compositions according to the invention.
The surface-active agent which can be used in association with the active ingredient in the compositions according to the invention, and being compatible therewith, may be an emulsifier, a dispersant or a wetting agent, each of which may be ionic or non-ionic. Advantageously the surface-active agent is selected from among the following families of surface-active agents which can be used in agriculture::
- sulphosuccinates and particularly dialkyl esters of sodium sulphosuccinate such as sodium dioctyl sulphonsuccinate;
- ethocylated alkyl phenols, and particularly addition products of octyl, nonyl or dodecyl phenol and ethylene oxide, such as nonyl phenyl with 6 mols of ethylene oxide;
- ethoxylated aliphatic alcohols and particularly C10 to C18 alcohols comprising from 5 to 60 mols of ethylene oxide;
- derivatives of quaternary ammonium and particularlytetraalkyl ammonium chlorides such as dimethyl dilauryl ammonium chloride ortrimethyl alkyl ammonium chloride,
- taurates such as sodium N-methyl or N-oleyl taurate,
- phosphates such as nonylphenol phosphate acid with 9 mols of ethylene oxide;
- alkyl aryl sulphonates such as sodium isopropyl naphthalene sulphonate;;
- ethoxylated aliphatic acids such as ethoxylated caster oil.
These different families of surface-active agents are described, for example, in the work entitled "Mc
Cutcheon's Detergents Emulsifiers" International Edition - 1979 -Annual. C.
The surface-active agents listed in the experiments numbers 1 to 11 from Example 1 may be mentioned as examples of surface-active agents which can be used according to the present invention. However, either aerosol OTB (mixture of sodium dioctylsulphosuccinate and sodium benzoate), orArquad 2C 50 (dimethyl dilauryl ammonium chloride), or Celanol DOS 75 (sodium di-octylsulphosuccinate) are preferably used as the surface-active agent.
Besides the active ingredient and one surface-active agent, the compositions of the invention may contain a carrier as well as one or more additives, for example, penetration agents, protective colloids, adhesives or thickening agents, anti-caking agents, colorants and thixotropic agents, for example, as well as possibly other known active ingredients containing pesticidal properties.
The term "carrier", in the present context designates a substance, which maybe organic or inorganic, natural or synthetic, with which the active ingredient is associated in order to facilitate its application to plants or its transport or manipulation. The carrier may be a solid (e.g. clays, natural or synthetic silicates, ammonium or sodium sulphates, resins, waxes or solid fertilisers) or liquid (e.g. water, petrol fraction, saturated chloro hydrocarbons or liquified gas).
The compositions according to the invention may be prepared in the form of water-soluble powders, wettable powders, solutions, emulsions, concentrates in a suspension and aerosols. The water-soluble powders are obtained by mixing from 20 to 99% by weight of the active ingredient, from 0.5 to 5% of the surface-active agents, from 0 to 10% of an anti-caking agent, the balance being a water-soluble substance, principally a water-soluble salt such as an ammonium or sodium sulphate.
By way of example, a water-soluble powder according to the invention may be composed of the following (by weight).
- ammonium persulphate 97.6% - aerosol OTB 2.4%
Another example of the water-soluble powder of the invention is composed of the following substances by weight: - ammonium persulphate 94.6% - aerosol OTB 2.4% - anti-caking silica 3.0%
The wettable powders usually comprise from 25 to 99% by weight of active ingredient and they generally contain, in addition to a solid carrier, from 1 to 5% of a wetting agent and/or other additives such as penetration agents, dispersants, adhesives, anti-caking agents and colorants.
There follows by way of example the composition by weight of a wettable powder according to the invention: - potassium persulphate 70% - anionic wetting agent
(Hostapon TPHC) 1% - deflocculant-(calcium
lignosulphate) 5% - anti-caking silica 5% - agent (kaolin) 19%
The concentrates in suspension which can also be used in spray form are prepared by obtaining a stable liquid product which does not settle and they usually contain from 10 to 70% by weight of an active ingredient, from 0.5 to 15% by weight of surface-active agents, from 0.1 to 10% by weight of thixotropic agents, and from 0 to 10% by weight of suitable additives such as anti-foaming agents, corrosion inhibitors, penetration agents and adhesives, and as a carrier, an organic liquid in which the active ingredient is slightly soluble or insoluble.
The compositions of the invention are preferably in the form of water-soluble powders containing from 80 to 99% by weight of potassium or ammonium persulphate from 0.5 to 5% by weight of a surface-active agent which is compatible with the active ingredient, from 0 to 10% of an anti-caking agent, the balance being a water-soluble substance.
In order to use the compositions mentioned above practically (i.e. in the form of water-soluble powders or wettable powders, or solutions or emulsions, or concentrations in suspension or aerosols) they are diluted, advantageously with water, in order to produce compositions wherein the active ingredient is in the form of an aqueous solution.
These compositions, which are also included within the scope of the present invention, besides comprising the active ingredient and the surface-active agent, contain water as well as conventional additives such as corrosion inhibitors, stabilisers and colorants. They generally contain from 0.11 to 80% by weight of the active ingredient.
The invention also provides a method for chemically hoeing fields and cultivated land, the method comprising applying to the aerial parts of the plants which are to be eliminated in these fields and cultivated areas a composition according to the invention.
The quantity of the active ingredient which is to be applied per m2 of land may vary according to the type of the vegetation to be eliminated and the particular method of application. Good results are obtained, for example, by applying from 5 to 20 g of alkali metal persulphate or ammonium persulphate per m2of land.
The areas are treated advantageously by using spray apparatus with a directed jet which allows the composition of the invention to be applied in a very localised manner to the area to be treated, and particularly to the weeds which are in this area, while carefully avoiding application of the composition outside this area.
The composition of the invention is particularly suitable for chemically hoeing cultivated land which is set out in lines such as orchards, vineyards, nurseries, garden plots and ornamental gardens.
Claims (13)
1. A herbicidal composition which comprises an effective amount of at least one metal or ammonium salt of persulphuric acid as an active ingredient, in association with at least one surface-active agent which is compatible therewith.
2. A composition according to claim 1,which comprises, as the active ingredient, a salt of the formula Me2S20s wherein Me represents an ammonium radical oran alkali metal.
3. A composition according to claim 2, wherein the active ingredient is ammonium persulphate.
4. A composition according to any one of claims 1 to 3, wherein the surface-active agent is selected from sulphosuccinates, ethoxylated alkylphenols, ethoxylated aliphatic alcohols, quaternary ammonium derivatives, taurates, phosphates, alkyl aryl sulphonates and ethoxylated aliphatic acids.
5. A composition according to any one of claims 1 to 4, wherein the surface-active agent comprises sodium dioctyl sulphosuccinate, optionally in a mixture with sodium benzoate.
6. A composition according to any one of claims 1 to 4, wherein the surface-active agent is dimethyl-dilauryl-ammonium chloride.
7. A composition according to any one of claims 1 to 6, wherein the composition is in the form of a water-soluble powder containing from 20 to 99% by weight of the active ingredient and from 0.5 to 5% of the surface-active agent.
8. A composition according to any one of claims 1 to 6, wherein the composition is in the form of a wettable powder, a solution, an emulsion, a concentrate in suspension or an aerosol.
9. A composition according to any one of claims 1 to 8, which comprises a carrier.
10. A composition according to claim 1 substantially as herein described with reference to any of the specific Examples.
11. A method of chemically hoeing fields and cultivated areas, wherein a composition according to any one of claims 1 to 10 is applied to the aerial parts of the plants which are to be eliminated in these fields and cultivated areas.
12. A method according to claim 9, in that the application is effected by using a compbsition which is obtained by diluting with water a composition according to claim 7 or 8.
13. A method according to claim 11 substantially as herein described with reference to any of the specific
Examples.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR7907465A FR2451713A1 (en) | 1979-03-19 | 1979-03-19 | HERBICIDE COMPOSITION FOR USE IN CHEMICAL HINKING OF SOILS AND CONTAINING AS ACTIVE SUBSTANCE AT LEAST ONE ALKALINE, ALKALINE EARTH OR AMMONIUM SALT OF PERSULFURIC ACID |
Publications (2)
Publication Number | Publication Date |
---|---|
GB2047098A true GB2047098A (en) | 1980-11-26 |
GB2047098B GB2047098B (en) | 1983-02-23 |
Family
ID=9223528
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB8008670A Expired GB2047098B (en) | 1979-03-19 | 1980-03-14 | Herbicidal composition |
Country Status (18)
Country | Link |
---|---|
JP (1) | JPS55129212A (en) |
AT (1) | AT366234B (en) |
BE (1) | BE882317A (en) |
CA (1) | CA1142769A (en) |
CH (1) | CH642232A5 (en) |
DE (1) | DE3010582A1 (en) |
DK (1) | DK115980A (en) |
ES (1) | ES8205524A1 (en) |
FR (1) | FR2451713A1 (en) |
GB (1) | GB2047098B (en) |
GR (1) | GR67196B (en) |
IE (1) | IE49560B1 (en) |
IT (1) | IT8048174A0 (en) |
LU (1) | LU82268A1 (en) |
NL (1) | NL8001434A (en) |
PT (1) | PT70962B (en) |
SE (1) | SE8002113L (en) |
ZA (1) | ZA801257B (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5464807A (en) * | 1990-02-05 | 1995-11-07 | Monsanto Company | Methods of using glyphosate compositions comprising alkoxylated quaternary ammonium surfactants |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR622405A (en) * | 1926-10-01 | 1927-05-30 | Herbicide product | |
JPS5273439A (en) * | 1975-12-16 | 1977-06-20 | Kikai Kouei Kk | Method of constructing passageway for lift |
-
1979
- 1979-03-19 FR FR7907465A patent/FR2451713A1/en active Pending
-
1980
- 1980-03-04 ZA ZA00801257A patent/ZA801257B/en unknown
- 1980-03-11 NL NL8001434A patent/NL8001434A/en not_active Application Discontinuation
- 1980-03-14 IT IT8048174A patent/IT8048174A0/en unknown
- 1980-03-14 GB GB8008670A patent/GB2047098B/en not_active Expired
- 1980-03-17 PT PT70962A patent/PT70962B/en unknown
- 1980-03-17 GR GR61467A patent/GR67196B/el unknown
- 1980-03-18 SE SE8002113A patent/SE8002113L/en not_active Application Discontinuation
- 1980-03-18 DK DK115980A patent/DK115980A/en not_active Application Discontinuation
- 1980-03-18 ES ES489666A patent/ES8205524A1/en not_active Expired
- 1980-03-18 IE IE554/80A patent/IE49560B1/en unknown
- 1980-03-18 LU LU82268A patent/LU82268A1/en unknown
- 1980-03-18 CA CA000347847A patent/CA1142769A/en not_active Expired
- 1980-03-18 JP JP3465780A patent/JPS55129212A/en active Pending
- 1980-03-19 BE BE0/199863A patent/BE882317A/en not_active IP Right Cessation
- 1980-03-19 DE DE3010582A patent/DE3010582A1/en not_active Withdrawn
- 1980-03-19 CH CH216880A patent/CH642232A5/en not_active IP Right Cessation
- 1980-03-19 AT AT0149880A patent/AT366234B/en not_active IP Right Cessation
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5464807A (en) * | 1990-02-05 | 1995-11-07 | Monsanto Company | Methods of using glyphosate compositions comprising alkoxylated quaternary ammonium surfactants |
Also Published As
Publication number | Publication date |
---|---|
ZA801257B (en) | 1981-10-28 |
DK115980A (en) | 1980-09-20 |
IE49560B1 (en) | 1985-10-30 |
IE800554L (en) | 1980-09-19 |
CH642232A5 (en) | 1984-04-13 |
GB2047098B (en) | 1983-02-23 |
AT366234B (en) | 1982-03-25 |
NL8001434A (en) | 1980-09-23 |
IT8048174A0 (en) | 1980-03-14 |
LU82268A1 (en) | 1981-10-30 |
SE8002113L (en) | 1980-09-20 |
ES489666A0 (en) | 1982-02-16 |
ATA149880A (en) | 1981-08-15 |
ES8205524A1 (en) | 1982-02-16 |
FR2451713A1 (en) | 1980-10-17 |
PT70962A (en) | 1980-04-01 |
BE882317A (en) | 1980-09-19 |
PT70962B (en) | 1983-02-01 |
CA1142769A (en) | 1983-03-15 |
JPS55129212A (en) | 1980-10-06 |
DE3010582A1 (en) | 1980-09-25 |
GR67196B (en) | 1981-06-24 |
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Legal Events
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PCNP | Patent ceased through non-payment of renewal fee |