RU2291619C2 - Aqueous herbicidal concentrate compositions, method for reducing of surfactant content in said composition, method for suppression of imopea growth, solid herbicidal concentrate composition - Google Patents

Abstract

FIELD: agriculture, herbicides.

SUBSTANCE: invention relates to aqueous herbicidal concentrate compositions containing glyphosate or salt thereof dissolved in aqueous medium,, surfactant in solution or in form of stable suspension, emulsion or dispersion in said medium, oxalic acid or salt thereof wherein ratio of surfactant and oxalic acid or salt thereof is from 5:1 to 40:1 and ratio of glyphosate or salt thereof based on acidic equivalent and oxalic acid or salt thereof is from 2:1 to 125:1. Also disclosed are method for reducing of surfactant content in said composition including dilution thereof with water; method for suppression of imopea growth by applying of aqueous composition on imopea leaves, as well as solid herbicidal concentrate composition containing glyphosate ammonium salt, oxalic acid or salt thereof and surfactant.

EFFECT: compositions of increased effectiveness.

21 cl, 191 tbl, 99 ex

Description

BACKGROUND OF THE INVENTION

The present invention relates to a method for increasing the herbicidal efficacy of glyphosate using organic acids. More specifically, the present invention relates to a method for increasing the herbicidal efficacy of a glyphosate potassium salt concentrate and compositions miscible in a reservoir and containing one or more surfactants by adding a component such as polycarboxylic acid or another component that increases the permeability of the cell membrane or inhibits oxidative flash.

Glyphosate is well known in the art as an effective post-emergence herbicide applied to plant leaves. In its acid form, glyphosate has the structure represented by formula (1):

and is relatively insoluble in water (1.16 wt.% at 25 ° C). For this reason, it is usually prepared in the form of a water-soluble salt.

Monobasic, dibasic and tribasic glyphosate salts can be prepared. However, in general glyphosate is preferably prepared and applied to plants in the form of a monobasic salt. The most widely used glyphosate salt is the mono (isopropylammonium) salt, often abbreviated as the IPA salt. Commercially available herbicides supplied by Monsanto Company and containing the glyphosate IPA salt as an active ingredient are Herbicides Roundup®, Roundup® Ultra, Roundup® UltraMax, Roundup® Xtra and Rodeo®. All of them are aqueous solution concentrate (SL) compositions and are usually diluted with water before application to the leaves of the plant. Another glyphosate salt, which is produced commercially as SL preparations, includes mono (trimethylsulfonium) and is often abbreviated as the TMS salt used, for example, in the Touchdown® herbicide from Syngenta. Various glyphosate salts, methods for producing glyphosate salts, preparations of glyphosate or its salts and methods for using glyphosate or its salts to kill or inhibit the growth of weeds and other plants are described in US Pat. No. 4,507,050, Bakel, in US Pat. No. 4405531, Franz, in US patent No. 4315765, Large, in US patent No. 4140513, Prill, in US patent No. 3977860, Franz, in US patent No. 3853530, Franz, and in US patent No. 3799758, Franz. The aforementioned patents in their entirety are incorporated herein by reference.

Of the number of water-soluble salts of glyphosate, which are known in the literature, but which are not known about the industrial use, one can note a potassium salt having the structure represented by formula (2):

and predominantly present in ionic form in an aqueous solution at a pH of about 4. This salt is described, for example, in US Pat. No. 4,405,531 to Franz, cited above, as one of the glyphosate and "alkali metal" salts used as a herbicide, wherein one of these alkali metals, along with lithium, sodium, cesium and rubidium, is potassium. Example C describes the preparation of a monopotassium salt by reacting specific amounts of glyphosate in the form of an acid and potassium carbonate in an aqueous medium.

Only very few herbicides are produced by industry in the form of their potassium salts. The Pesticide Manual, Pesticide Manual, 11th Edition, 1997, lists herbicides obtained in the form of potassium salts, namely herbicides such as auxin, 2,4-DB ((2,4-dichlorophenoxy) butanoic acid), dicamba (3.6 -dichloro-2-methoxybenzoic acid), dichloroprop (2- (2,4-dichlorophenoxy) propanoic acid), MCPA ((4-chloro-2-methylphenoxy) acetic acid) and picloram (4-amino-3,5,6 trichloro-2-pyridinecarboxylic acid), the active ingredient of some herbicidal products being supplied by DowElanco under the trademark Tordon.

The solubility of the potassium salt of glyphosate in water is reported in the pending application, Reg. No. 09/444766, filed November 22, 1999, the description of which in its entirety is incorporated into this application by reference. The glyphosate potassium salt described in this application has a solubility in pure water at 20 ° C. of about 54% by weight, i.e. approximately 44% of the acid equivalent of glyphosate (ke) by weight. This solubility is almost similar to the solubility of the IPA salt. Concentrations, expressed as percentages by weight, mean parts by weight of salt or acid equivalent (ke) per 100 parts by weight of the solution. Thus, a simple aqueous concentrate of glyphosate potassium salt solution can be easily obtained at a concentration of, for example, 44% ke. by weight, in contrast to the commercially available preparation with the IPA salt of glyphosate, obtained in the form of an aqueous solution concentrate, supplied by the company Monsanto Company under the name D-Pak. Slightly higher concentrations can be obtained by slightly neutralizing, for example, a 5-10% aqueous solution of glyphosate potassium salt with potassium hydroxide.

Polycarboxylic acid has been used as chelating agents to increase the effectiveness of glyphosate in tank-miscible formulations. So, for example, D.J. Turner, in Butterworths (1985), pages 229-230, reports that a 2% concentration of polycarboxylic acids in glyphosate reservoir mixtures (Roundup®) provides an increase in efficiency. In addition, Research Disclosure publication number RD15334, Industrial Opportunities Ltd., Homewell-Havant-Hampshire P09 1EF, United Kingdom (January, 1977) indicates that glyphosate mixtures obtained in the tank are prepared with water containing calcium ions and / or magnesium in a concentration of more than 200 ppm (hard water), have reduced herbicidal activity. Herbicidal activity is restored by adding oxalic acid to the tank mixture at mass ratios to glyphosate of about 1:10 to 10: 1.

US Pat. No. 5,863,863 to Hasabe et al. Describes reservoir mixture preparations containing about 0.08% by weight of a.i. IPA glyphosate (like Roundup®) and about 0.001 mol / L dipotassium, disodium, diammonium, diethanolamine or dimethylaminoxalate, and surfactants based on ethoxylated tertiary amine or quaternary ammonium. Concentrates containing about 41% by weight of ai are also described. IPA glyphosate, 0.21 mol / kg dipotassium, disodium, diammonium, diethanolamine or dimethylaminoxalate.

In US patent No. 5525576, Medina-Vega et al. A method for producing an extract from a seed peel containing a mixture of polycarboxylic acids is described with a view to using it as an agent for assimilating the herbicide. 0.25% of the extract was added to tank mixes containing glyphosate trimethyl sulfonium salt (TMS) (commercially available under the trademark Touchdown®) or glyphosate isopropylamine salt (IPA) (commercially available under the Roundup® trademark). US Pat. No. 5,436,220, Hickey, describes a highly effective preparation comprising an extract from seed peels containing tricarboxylic acids and Roundup® herbicide, with glyphosate application rates of 64 to 191 g / ha in combination with an application rate of 82 g / ha of extract from peel seeds containing about 5 wt.% tricarboxylic acid.

US Pat. Nos. 5,849,663 and 6,008,158, Hasabe et al., Describe tank-miscible compositions containing Roundup® herbicide at 0.08% by weight of active ingredient (ai) or TMS glyphosate; chelating agents based on salts of polycarboxylic acids, including oxalic acid salts at 0.02 wt.%; and ethoxylated tertiary amine and quaternary ammonium as surfactants. Hasabe reports that the mass ratios of polycarboxylic acid to surfactant are from about 1: 2 to 1: 9, with an increase in efficiency due to the formation of complexes with metal ions.

US Pat. No. 6,093,679 to Azuma et al. Describes reservoir-mixed compositions containing 0.38 wt.% TMS glyphosate (Touchdown®), 0.53 wt.% Chelating agents based on hydroxycarboxylic acid, including potassium oxalate, and quaternary ammonium surfactant containing an alkoxylated carboxyalkyl anion.

US Pat. No. 6,218,336 to Coleman describes reservoir mixtures containing up to 1.25 wt.% Roundup® Ultra IPA glyphosate and 2.5 wt.% Succinic, tartaric or malic acid or their ammonium salts. Sylgard 309® (ethoxylated organosilicon compound) and Emsorb 6900® surfactant (polyoxyethylene sorbitol ester) can be added to these tank mixes.

US Pat. No. 5,948,421 to Okano et al., Discloses aqueous concentrate compositions containing 42 and 51 wt.% Respectively glyphosate diammonium or isopropylamine salts, dicarboxylic acid chelating agents, including potassium oxalate in an amount of 8 wt.%, And ethoxylated quaternary ammonium as a surfactant.

At the same time, nothing is reported about the effectiveness of polycarboxylic acids in glyphosate potassium salt preparations. This is probably due to the fact that the commercial use of potassium herbicide preparations is limited, and the effect of polycarboxylic acids on the numerous surfactants used in the industry for the manufacture of herbicides varies and is unpredictable.

The choice of surfactant is the main factor affecting the effectiveness of the herbicide. For example, as a result of intensive research conducted by Wyrill & Burnside and described in Weed Science, 1977, volume 25, pages 275-287, it was found that various surfactants vary widely in their ability to increase the herbicidal efficacy of glyphosate, introduced as an IPA salt. Surfactants suitable for the preparation of glyphosate potassium salt preparations are described in the pending application, Reg. No. 09/926521, filed November 14, 2001 (national phase of International Application No. PCT / US01 / 16550, filed May 21, 2001), complete the description of which is incorporated into the present invention by reference. Surfactants capable of significantly increasing the herbicidal efficacy of glyphosate are mainly, but not exclusively, cationic surfactants, including surfactants that form cations in an aqueous solution or dispersion at pH values of about 4-5, monobasic glyphosate salts characteristic of SL preparations.

Somewhat beyond the scope of broad generalizations, it can be noted that the relative ability of various surfactants to increase the herbicidal efficacy of glyphosate is largely unpredictable.

The surfactants that contribute most to the glyphosate's herbicidal efficacy are mainly, but not exclusively, cationic surfactants, including surfactants that form cations in an aqueous solution or dispersion at pH values of about 4- 5, typical for SL preparations of monobasic glyphosate salts. Examples of surfactants include long chain (typically C ₁₂ -C ₁₈ ) tertiary alkylamine and quaternary alkyl ammonium. The most well-known tertiary alkylamine surfactant used in aqueous compositions of a concentrate of a solution of IPA salt of glyphosate is a highly hydrophilic surfactant polyoxyethylene-talloamine (15), i.e. tallowamine having, in total, about 15 mol of ethylene oxide in two polymerized ethylene oxide chains attached to an amino group, as shown in formula (3):

where R is a mixture consisting mainly of C ₁₆ and C ₁₈ alkyl and alkenyl chains derived from tall oil, and the sum m + n is equal to an average of about 15.

It has been found that for some applications it is desirable to use a slightly less hydrophilic alkylamine surfactant, such that has less than about 10 moles of ethylene oxide, as indicated in US Pat. No. 5,668,085, Forbes et al., For example, polyoxyethylene (2) -cocoamine. This patent describes illustrative aqueous compositions containing said surfactant together with an IPA salt, ammonium or potassium salt of glyphosate. The highest concentration of glyphosate in this composition with potassium salt, presented in table 3 of the patent '085, is 300 grams ke glyphosate / l, and the mass ratio of ke glyphosate to the surfactant is 2: 1.

WO 00/59302 describes a class of alkoxylated alkyl amines used in sprayable herbicidal compositions. This application also describes solutions of the potassium salt of glyphosate, including various EO / PO propylamines or -propildiaminy Jeffamine ^TM.

A wide range of quaternary ammonium surfactants have been described as components of aqueous compositions of a concentrate of a solution of the IPA salt of glyphosate. Illustrative examples are N-methylpolyoxyethylene (2) -coammonium chloride described in European Patent No. 0274369, N-methylpolyoxyethylene (15) -coammonium chloride described in US Pat. No. 5,317,003, and various quaternary ammonium compounds having the formula (4):

where each of R ¹ , R ² and R ³ represents C _1-3 alkyl groups, and n represents an average of 2 to 20,

and described in US patent 5464807.

PCT Publication No. WO 95/16969 describes aqueous solution concentrate compositions containing glyphosate in the form of an IPA salt, methyl ammonium and diammonium salts, a quaternary ammonium surfactant and an acid salt of a primary, secondary or tertiary alkylamine compound.

It has been reported that other cationic surfactants, including those described in PCT Publication No. WO 95/33379, can be used in aqueous compositions of a concentrate of a solution of glyphosate salts. In addition, PCT publication No. WO 97/32476 reported that highly concentrated aqueous glyphosate salts compositions can be prepared using the same cationic surfactants, but with the addition of a specific component that enhances the stability of these compositions. In this work, IPA salt and mono- and diammonium salts are mentioned as examples of glyphosate salts.

US Pat. No. 5,750,468 describes a class of surfactants comprising alkyl ether, amide salts of alkyl ether and ammonium oxide, which are suitable for preparing aqueous solution concentrate compositions containing various glyphosate salts, the potassium salt being mentioned in the list of salts. This patent indicates that the advantage of the surfactants in question used in aqueous compositions together with glyphosate salts is that these surfactants can increase the concentration of glyphosate to very high levels.

Anionic surfactants, with the exception of their use in combination with cationic surfactants, as described in US Pat. No. 5,389,598 and US Pat. No. 5,703,015, are generally not of interest in terms of their use in the glyphosate IPA salt formulations. The '015 patent describes a mixture of surfactants, such as dialkoxylated alkylamine and an anionic compound that reduces eye irritation. This mixture is indicated to be suitable for the preparation of aqueous solution concentrate compositions containing glyphosate salts, with a potassium salt being mentioned in the list of these salts. The concentrates described in the '015 patent contain from about 5 to 50%, preferably from about 35% to 45% glyphosate active ingredient (ai) and from about 5 to 25% surfactant. In addition, PCT application publication No. WO 00/08927 describes the use of certain polyalkoxylated phosphoric acid esters in combination with certain amidoamines in glyphosate-containing compositions. Potassium salt has been identified as one of several “suitable” glyphosate salts.

In general, non-ionic surfactants have been reported to be less effective in enhancing herbicidal activity than cationic or amphoteric surfactants when used as a separate surfactant in the SL composition of the IPA glyphosate salt, with the exception, obviously, certain alkyl polyglucosides described, for example, in Australian Patent No. 627503, and polyoxyethylene (10-100) C _16-22 alkyl esters described in PCT Application Publication No. WO 98/17109. Other non-ionic surfactants are usually mixed with cationic surfactants to form a surfactant system for use in liquid herbicidal concentrates. However, cationic / nonionic surfactant systems generally do not provide acceptable storage stability at low temperatures. Concentrates containing such surfactant systems can crystallize at temperatures of about 0 ° C and at lower temperatures, which limits the use of such concentrates in cold climates.

Glyphosate concentrates containing nonionic alkyl ether and cationogenic amine surfactants are described in US Pat. No. 6,245,713. It has been reported that such a mixture of surfactants enhances the glyphosate's biological effectiveness and provides increased resistance to precipitation. Glyphosates suitable for use in these concentrates are sodium, potassium, ammonium, dimethyl ammonium, IPA, monoethanol ammonium and TMS salts of glyphosate. This patent is in its entirety incorporated herein by reference.

There is good reason to believe that the potassium salt of glyphosate, used as a herbicidal active ingredient, will eliminate the relative difficulties encountered in the preparation of this salt as a highly concentrated SL product together with surfactants of the preferred type. Thus, for example, a surfactant widely used in the compositions of the IPA salt of glyphosate, namely the polyoxyethylene (15) -talloamine of formula (3), mentioned above, is highly incompatible with the potassium salt of glyphosate in aqueous solution. In addition, PCT application publication No. WO 00/15037 noted low compatibility of alkoxylated alkylamine surfactants, mainly with concentrates having a high glyphosate content. As shown in this publication, in order to achieve an effective level of surfactant, an alkyl glycoside surfactant is used in combination with an alkoxylated alkylamine surfactant to produce highly concentrated concentrates containing glyphosate potassium salt.

The addition of such alkyl glycosides results in compositions with a higher viscosity (compared to compositions without alkyl glycosides). Such an increase in viscosity of these highly concentrated compositions is undesirable for various reasons. In addition to the difficulties that arise when pouring these compositions from the container or removing their residues during washing, the undesirable effects associated with the increased viscosity of the compositions are especially pronounced if these mixtures must be pumped. Increasing volumes of glyphosate liquid water products are bought by consumers in large, refillable (replaceable) containers, pneumatic containers, sometimes called shuttles, shuttles, which usually have an integrated pump or device to connect to an external pump that allows fluid to be supplied. Glyphosate liquid water products are also transported in large volume containers with capacities of up to about 100,000 liters. This liquid is usually transferred by pumping to a storage tank, which is carried out on the equipment of wholesalers, retailers or cooperatives, after which this liquid can be transferred to a pneumatic container or to small containers for further distribution. Since large quantities of glyphosate compositions are purchased and transported in early spring, it is imperative that such compositions can be pumped at low temperatures.

When such alkyl glycosides (for example, Agrimul ^™ APG-2067 and 2-ethyl-hexyl glucoside) are added to the glyphosate concentrate, this concentrate acquires a dark brown color. Moreover, it is desirable that the glyphosate concentrate has a lighter color than the alkyl glycoside-containing concentrates described in WO 00/15037, which have a color intensity of about 10 to 18, as measured using a Gardner colorimeter. When dye is added to a glyphosate concentrate having a Gardner color intensity of 18, this concentrate acquires a dark brown color. Concentrates having a Gardner color intensity of 10 are poorly stained in various colors, for example blue, green, red or yellow, which often need to be stained with concentrates to distinguish the glyphosate product from other herbicidal products.

It would be desirable to obtain a stable, long-term storage composition of an aqueous glyphosate potassium salt concentrate having an agriculturally acceptable surfactant content or “fully loaded” with a surfactant. These compositions have a reduced viscosity such that they can be pumped using standard volumetric pumping equipment at 0 ° C, at a speed of at least 7.5 gallons per minute, usually more than 10 gallons per minute, and preferably more than 12.5 gallons per minute. The term "agriculturally acceptable surfactant content" means the content of one or more surfactants of this type or types and in such an amount that when using this composition gives a positive effect in terms of its herbicidal effect compared to another similar composition, not containing surfactant. The term "full load" means a concentration of a suitable surfactant sufficient to achieve, after appropriate dilution in water and application to the leaves, herbicidal efficacy to control one or more major weed species without additional addition of the surfactant to the diluted composition.

The term "storage stability", referring to the composition of an aqueous concentrate of glyphosate salt, which, in addition, contains a surfactant, means that in this composition phase separation does not occur at temperatures up to about 50 ° C, and preferably glyphosate crystals do not form or its salt at a temperature of about 0 ° C for a period of time up to about 7 days (that is, the specified composition should have a crystallization point at 0 ° C or lower). For aqueous solution concentrates, storage stability at high temperatures is often characterized by a cloud point of about 50 ° C. or higher. The cloud point of a composition is usually determined by heating the composition until the solution becomes cloudy, after which the composition is left to cool with stirring and its temperature is continuously monitored. The cloud point is the temperature that is recorded at the moment when the solution begins to become transparent. A cloud point of 50 ° C. or higher is generally considered to be a temperature acceptable for most commercial applications of the glyphosate composition SL. Ideally, the cloud point should be 60 ° C. or more, and the composition should be maintained at temperatures of at least about −10 ° C., and preferably at least about −20 ° C. for about 7 days without crystal growth even in the presence of crystallization nuclei of glyphosate salt.

The surfactant described herein as “compatible” with glyphosate salt at certain concentrations of surfactant and ke glyphosate, is a surfactant that provides a storage stable aqueous concentrate, defined immediately above and containing the specified surfactant and salt in certain concentrations.

Users working with liquid herbicidal products usually measure the dose by volume rather than by weight, and such products are usually provided with guidelines for their application rate expressed in volume per unit area, for example in liters per hectare (l / ha) or in liquid ounces per acre (ounce / acre). Thus, the concentration of the herbicidal active ingredient the consumer is dealing with is not expressed as a percentage by weight but as a mass per unit volume, for example, in grams per liter (g / l) or in pounds per gallon (lb / gallon). In the case of glyphosate salts, the concentration is often expressed in grams of acid equivalent per liter (gram ke / l).

Historically, surfactant-containing glyphosate IPA salts products, such as the Rounds® and Roundup® Ultra herbicides from Monsanto Company, are most often made at glyphosate concentrations of about 360 gf.e./l. The surfactant containing Syngenta Touchdown® glyphosate TMS salt product was prepared at a glyphosate concentration of about 330 g ke / l. Products with a low concentration of ke, i.e. more diluted ones are also commercially available in some markets, but the manufacture of such products entails material losses per unit of glyphosate contained in them, which is caused by costs associated mainly with their packaging, delivery, and storage in warehouses.

An additional reduction in production costs and ease of use can be achieved by preparing a “fully loaded” aqueous concentrate composition, or at least a composition having an agriculturally acceptable surfactant content, at a glyphosate concentration of at least about 320 g ke / l, 340 g ke / l or significantly higher than 360 g ke / l, for example at least about 420 g ke / l or higher, or at least 440, 450, 460, 470, 480, 490, 500, 510, 520, 530, 540, 550, 560, 570, 580, 590, 660 g ke / l or Shae.

When using very high concentrations of ke glyphosate, such as the concentrations listed above, usually a serious problem occurs. It is associated with the difficulty of pouring and / or pumping an aqueous concentrate, which is due to the high viscosity of this concentrate, and this is especially true at low temperatures. Therefore, it would be desirable to obtain a highly concentrated aqueous solution of glyphosate potassium salt fully loaded with an agriculturally acceptable surfactant, but such a composition should preferably be less viscous than glyphosate potassium salt compositions containing alkyl glycoside surfactants, such as those described PCT Application Publication No. WO 00/15037.

Significant commercial advantage can be achieved by increasing the efficiency of glyphosate potassium salt compositions. Higher efficiency allows to achieve a similar degree of weed control with a lower rate of application of the herbicide. Introducing less herbicide has an economic benefit for the consumer, since with less product an equivalent level of weed control is achieved. In addition, this composition with increased efficiency is environmentally friendly due to the reduction in packaging volume requires less storage space, saves money associated with delivery, and most importantly, gives a minimal load on the environment. These and other advantages of the present invention will be apparent from the following description.

SUMMARY OF THE INVENTION

Therefore, among several distinctive features of the present invention, it is possible to obtain a pesticidal composition that can be used in agriculture, where this composition is prepared so that it includes a compound that increases the permeability of the cell membrane; obtaining herbicidal compositions having an increased inhibitory effect against a wide range of broad-leaved plants, including Theophrastus and Ipomoea; obtaining storage stable herbicidal concentrates, which are prepared using a minimum amount of surfactant in order to reduce the aqueous toxicity of this composition without reducing its effectiveness; and obtaining stable during storage of solid and liquid concentrates, which can be easily diluted and are easy to handle.

Briefly, the present invention relates to an aqueous composition of a pesticidal concentrate containing a water-soluble pesticide dissolved in an aqueous medium, a surfactant component and a compound that increases the absorption of the pesticide by plant cells. This water-soluble pesticide is present in a concentration that is biologically effective when the specified composition is diluted in a suitable volume of water to form a mixture for applying an enhanced effect and applying this mixture to leaves of an action-sensitive pesticide, i.e. susceptible plants. The surfactant component is present in solution or in a stable suspension, emulsion or dispersion in an aqueous medium. This surfactant component includes one or more surfactants and a compound that increases the permeability of the cell membrane in the plant, increasing the cellular uptake of the pesticide by the plant treated with the specified mixture for application of enhanced action compared with the plant treated with a standard mixture for applying, not containing the specified compound, but otherwise having the same composition as the specified mixture for applying enhanced action. The specified compound and surface-active component are present in a molar ratio in excess of 10: 1.

The present invention also relates to an aqueous composition of a herbicidal concentrate comprising glyphosate or a salt or ester thereof and a compound that increases the permeability of the cell membrane in a plant. The glyphosate component is present in solution in an aqueous medium at a concentration exceeding 455 grams of the acid equivalent (ke) of glyphosate per liter. When the specified composition is diluted in a suitable volume of water with the formation of a mixture for applying an enhanced effect and applying this mixture to the leaves of a susceptible plant, the glyphosate uptake of the plant cells treated with the specified enhanced uptake increases compared to the glyphosate uptake in a plant treated with a standard application mixture. containing the specified compound, but otherwise having the same composition as the specified mixture for applying enhanced action.

In yet another embodiment, the present invention relates to an aqueous composition of a herbicidal concentrate comprising glyphosate and a compound that enhances cellular uptake of glyphosate. Glyphosate is present predominantly in the form of potassium, mono-ammonium, diammonium, sodium, monoethanolamine, n-propylamine, ethylamine, ethylenediamine, hexamethylene diamine or trimethylsulfonium salt in solution in an aqueous medium. The cellular uptake of glyphosate increases with increasing permeability of the cell membrane in a plant treated with the indicated enhanced mixture, increases compared with the uptake of glyphosate with a plant treated with a standard application mixture that does not contain the specified compound, but otherwise having the same composition as the specified mixture for application of enhanced action. The specified concentrate is biologically effective in diluting the composition in a suitable volume of water with the formation of a mixture for applying enhanced action and applying this mixture to the leaves of a susceptible plant.

In another embodiment, the present invention relates to an aqueous composition of a herbicidal concentrate comprising glyphosate and a compound that enhances the uptake of glyphosate by cells. Glyphosate is present primarily in the form of its potassium salt in solution in an aqueous medium. Cellular absorption of glyphosate increases with increasing permeability of the cell membrane in a plant treated with the indicated enhanced mixture compared to the absorption of glyphosate in a plant treated with a standard application mixture that does not contain the specified compound, but otherwise having the same composition as the specified mixture for application of enhanced action. The specified composition is biologically effective in diluting the composition in a suitable volume of water with the formation of a mixture for applying enhanced action and applying this mixture to the leaves of a susceptible plant.

The present invention also relates to an aqueous composition of a pesticidal concentrate containing a water-soluble pesticide dissolved in an aqueous medium, a surfactant component and a compound that suppresses an oxidative burst (oxidative burst). This water-soluble pesticide is present in a concentration that is biologically effective when the composition is diluted in a suitable volume of water to form a mixture for applying enhanced action and applying this mixture to the leaves of a susceptible plant. The surfactant component includes one or more surfactants in solution or in a stable suspension, emulsion or dispersion in said medium. The specified compound, which suppresses the oxidative burst in the cells of the plant, interferes with the protective response of the plant treated with the specified mixture for application of enhanced action, compared with a plant treated with a standard mixture for application that does not contain the specified compound, but otherwise having the same composition as specified mixture for applying enhanced action. The specified compound and surface-active components are present in a molar ratio in excess of 10: 1.

In addition, the present invention relates to an aqueous composition of a herbicidal concentrate comprising glyphosate or a salt or ester thereof, and a compound that suppresses an oxidative burst in plant cells. The glyphosate component is present in solution in an aqueous medium at a concentration exceeding 455 grams of the acid equivalent (ke) of glyphosate per liter. When a specified composition is diluted in a suitable volume of water with the formation of a mixture for applying an enhanced effect and applying this mixture to the leaves of a susceptible plant, the protective response of a plant treated with the specified enhanced mixture is reduced compared to the protective response of a plant treated with a standard application mixture, containing the specified compound, but otherwise having the same composition as the specified mixture for applying enhanced action.

In yet another embodiment, the present invention relates to an aqueous composition of a herbicidal concentrate comprising glyphosate and a compound that inhibits oxidative burst in plant cells. Glyphosate is present predominantly in the form of its potassium, mono-ammonium, diammonium, sodium, monoethanolamine, n-propylamine, ethylamine, ethylenediamine, hexamethylene diamine or trimethylsulfonium salts in solution in an aqueous medium, in a concentration that is biologically effective when diluted with water the formation of a mixture for applying enhanced action and applying this mixture to the leaves of a susceptible plant. The specified compound, which suppresses the oxidative burst in the cells of the plant, interferes with the protective response of the plant treated with the specified mixture for application of enhanced action, compared with a plant treated with a standard mixture for application that does not contain the specified compound, but otherwise having the same composition as specified mixture for applying enhanced action.

In another embodiment, the present invention relates to an aqueous composition of a herbicidal concentrate comprising glyphosate, present predominantly in the form of its potassium salt in solution in an aqueous medium, in a concentration that is biologically effective when the composition is diluted in a suitable volume of water to form a mixture for enhanced action and applying this mixture to the leaves of a susceptible plant. The specified composition, in addition, includes a compound that suppresses an oxidative burst in the cells of the plant and thereby inhibits the protective response of the plant treated with the specified mixture for application of enhanced action, compared with a plant treated with a standard mixture for application that does not contain the specified compound, but in otherwise having the same composition as the specified mixture for applying enhanced action.

In another embodiment, the present invention relates to an aqueous composition of a herbicidal concentrate comprising glyphosate or its salt or ester and oxalic acid or its salt or ester. Glyphosate is present in solution in an aqueous medium at a concentration exceeding 455 grams ke. glyphosate per liter. When the specified composition is diluted in a suitable volume of water with the formation of a mixture for applying an enhanced effect and applying this mixture on the leaves of a susceptible plant, plant growth is suppressed to a greater extent than the growth of a plant treated with a standard application mixture that does not contain oxalic acid and the specified salt or complex ether, but otherwise having the same composition as the specified mixture for applying enhanced action.

In yet another embodiment, the present invention relates to an aqueous solution comprising glyphosate and oxalic acid or a salt or ester thereof. Glyphosate is present predominantly in the form of its potassium salt in a concentration that is biologically effective when the composition is diluted in a suitable volume of water to form a mixture for applying enhanced action and applying this mixture to the leaves of a susceptible broad-leaved plant. Oxalic acid or its salt or ester is present in such a concentration that plant growth is suppressed to a greater extent than the growth of a plant treated with a standard application mixture not containing oxalic acid and said salt or ester, but otherwise having the same composition, like the specified mixture for applying enhanced action.

In another embodiment, the present invention relates to an aqueous solution comprising glyphosate and oxalic acid or a salt or ester thereof. Glyphosate is present predominantly in the form of its diammonium salt in a concentration that is biologically effective when the composition is diluted in a suitable volume of water to form a mixture for applying enhanced action and applying this mixture to the leaves of a susceptible broad-leaved plant. Oxalic acid or its salt or ester is present in such a concentration that plant growth is suppressed to a greater extent than the growth of a plant treated with a standard application mixture not containing oxalic acid and its salt or ester, but otherwise having the same composition, like the specified mixture for applying enhanced action.

In another embodiment, the present invention relates to an aqueous solution containing glyphosate and an oxalic acid salt. Glyphosate or its salt or ester is present in the solution in a concentration that is biologically effective when the composition is diluted in a suitable volume of water to form a mixture for applying enhanced action and applying this mixture to the leaves of a susceptible plant. The oxalic acid salt includes a tetraalkylammonium or aryltrialkylammonium salt and is present in such a concentration that the growth of the plant treated with the enhanced application mixture is suppressed to a greater extent than the growth of the plant treated with the standard application mixture that does not contain the specified salt, but otherwise having such the same composition as the specified mixture for applying enhanced action.

In another embodiment, the present invention relates to an aqueous herbicidal composition comprising glyphosate, one or more surfactants, and oxalic acid or a salt and ester thereof. Glyphosate or its salt or ester is present in the solution in a concentration that is biologically effective when the composition is diluted in a suitable volume of water to form a mixture for applying enhanced action and applying this mixture to the leaves of a susceptible plant. Surfactant components are present in the form of a solution or a stable suspension, emulsion or dispersion in an aqueous medium together with oxalic acid or its salt or ester, where the concentration of oxalic acid or its salt or ester and the nature of the specified surfactant is such that difference between (first difference):

(i) the growth rate of a plant treated with the first enhanced application mixture obtained by diluting said aqueous composition of the herbicidal concentrate with water, and

(ii) the growth rate of a plant treated with the first standard application mixture, not containing oxalic acid or any of the salts or esters indicated, but otherwise having the same composition as the first enhanced application mixture

exceeds the difference between (second difference):

(iii) the growth rate of the plants treated with the second mixture for applying enhanced action, and

(iv) the growth rate of a plant treated with a second standard application mixture, not containing oxalic acid or any of the salts or esters indicated, but otherwise having the same composition as the second enhanced application mixture.

The composition of the specified second mixture for application of enhanced action differs from the composition of the specified first mixture for application of enhanced action only by the nature of the system of surfactants contained in this mixture, where the specified second mixture for application of enhanced action contains ethoxylated tallowamine as a surfactant having the formula:

where R is a mixture consisting predominantly of C ₁₆ and C ₁₈ alkyl and alkenyl chains derived from tall oil, and the sum m + n is an average of about 15; where the mass ratio of the acid equivalent (ke) of glyphosate to the surfactant in the second mixture for applying enhanced action is approximately 2: 1.

In yet another embodiment, the present invention relates to an aqueous herbicidal composition comprising glyphosate and oxalic acid, or a salt or ester thereof. Glyphosate or its salt or ester is present in a concentration exceeding 360 gram ke. glyphosate per liter. Oxalic acid or its salt or ester is present in such a concentration that when the specified composition is diluted in a suitable volume of water with the formation of a mixture for applying an enhanced effect and applying this mixture on the leaves of a susceptible broad-leaved plant, the growth of this plant is suppressed to a greater extent than the growth of broad-leaved plants treated with a standard mixture for application, where the composition of the specified standard mixture for application is different from the composition of the specified mixture for applying enhanced action I only in that it contains oxalic acid and its salt or ester thereof and contains ethylenediaminetetraacetic acid or sodium citrate.

In another embodiment, the present invention relates to an aqueous herbicidal composition comprising glyphosate or oxalic acid or a salt or ester thereof. Glyphosate or a salt or ester thereof is present in the solution in a concentration that is biologically effective when the composition is diluted in a suitable volume of water to form a mixture for applying enhanced action and applying this mixture to the leaves of a susceptible plant. Oxalic acid or its salt or ester is present in such a concentration that the growth of this plant is suppressed to a greater extent than the growth of a plant treated with a standard application mixture not containing oxalic acid and its salt or ester, but otherwise having the same composition as the specified mixture for applying enhanced action, where the specified composition has a density of at least about 1,210 grams / liter.

In yet another embodiment, the present invention relates to an aqueous composition of a herbicidal concentrate comprising glyphosate and oxalic acid or a salt or ester thereof. Glyphosate is predominantly present in the form of its potassium, mono-ammonium, di-ammonium, sodium, mono-ethanolamine, n-propylamine, ethylamine, ethylenediamine, hexamethylene diamine or trimethylsulfonium salts in a concentration that is biologically effective in the dilution of the specified composition in a mixture with a suitable amount of water and applying this mixture to the leaves of a susceptible plant. Oxalic acid or its salt or ester is present in a concentration at which the growth of this plant is suppressed to a greater extent than the growth of a plant treated with a standard application mixture not containing oxalic acid and its salt or ester, but otherwise having the same composition, as well as the specified mixture for applying enhanced action.

The present invention also relates to an aqueous herbicidal composition comprising glyphosate and oxalic acid or a salt or ester thereof. Glyphosate or a salt or ester thereof is present in the solution in a concentration that is biologically effective when the composition is diluted in a suitable volume of water to form a mixture for applying enhanced action and applying this mixture to the leaves of a susceptible plant. The acid equivalent (ke) of glyphosate and oxalic acid or its salt or ester are present in a weight ratio in excess of 21: 1.

In another embodiment, the present invention relates to an aqueous composition of a pesticidal concentrate containing a water-soluble pesticide dissolved in an aqueous medium; a surfactant and a compound that enhances the expression of hydroxyproline-rich glycoproteins. The specified water-soluble pesticide is present in a concentration that is biologically effective when the specified composition is diluted in a suitable volume of water to form a mixture for applying enhanced action and applying this mixture to the leaves of a susceptible plant. The specified surfactant component includes one or more surfactants and is present in the form of a solution or stable suspension, emulsion or dispersion in the specified environment. The specified compound, which increases the expression of hydroxyproline-rich glycoproteins, enhances the penetration of the pesticide into the phloem of the plant treated with the specified mixture for application of enhanced action, compared with a plant treated with a standard mixture for application that does not contain the specified compound, but otherwise having the same composition like the specified mixture for applying enhanced action. The specified compound and surface-active component are present in a molar ratio in excess of 10: 1.

In yet another embodiment, the present invention relates to an aqueous composition of a herbicidal concentrate comprising glyphosate and a compound that enhances the expression of hydroxyproline-rich glycoproteins. Glyphosate or its salt or ester is present in solution in a concentration exceeding 455 grams ke. glyphosate per liter. A compound that enhances the expression of hydroxyproline-rich glycoproteins is present in such a concentration that, when the composition is diluted in a suitable volume of water to form a mixture for application of enhanced effect and applied to the leaves of a susceptible plant, it enhances the penetration of said glyphosate into the phloem of the plant treated with said mixture for applying enhanced action, compared with a plant treated with a standard application mixture not containing the specified compound Ia, but otherwise having the same composition as said enhanced application mixture for action.

In another embodiment, the present invention relates to an aqueous composition of a herbicidal concentrate containing glyphosate, a surfactant component and oxalic acid or its salt or ester, where:

(i) glyphosate or a salt or ester thereof is present in the solution in a concentration that is biologically effective when the composition is diluted in a suitable volume of water and applied to the leaves of a susceptible plant;

(ii) a surfactant component is present in a solution or in a stable suspension, emulsion or dispersion in said medium and includes one or more surfactants, and

(iii) oxalic acid or a salt or ester thereof is present.

The specified surfactant component includes at least one surfactant selected from the group consisting of:

(a) an ester of phosphoric acid having the formula:

where R ¹ represents a straight or branched alkyl, straight or branched alkenyl, straight or branched alkynyl, aryl or aralkyl groups having from about 4 to 30 carbon atoms; R ² in each of the groups m (R ² O) independently represent C ₂ -C ₄ alkylene; and m is about 1 to 30;

(b) a phosphoric acid diester having the formula:

where R ¹ and R ³ independently represent a straight or branched alkyl, straight or branched alkenyl, straight or branched alkynyl, aryl or aralkyl groups having from about 4 to 30 carbon atoms; R ² in each of the groups m (R ² O) and n (R ² O) independently represent C ₂ -C ₄ alkylene; and m and n independently are from 1 to about 30;

(c) ethers having the formula:

where R ¹ represents hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms; R ² is hydrocarbylene or substituted hydrocarbylene having from 2 to about 30 carbon atoms; R ³ and R ⁴ independently represent hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, or - (R ⁵ O) _x R ⁶ , R ⁵ in each of the groups x (R ⁵ -O) independently represents C ₂ -C ₄ alkylene, R ⁶ represents hydrogen or a straight or branched alkyl group having from about 1 to 4 carbon atoms, and x represents an average of from 1 to about 50; and

d) monoalkoxylated quaternary ammonium salts of the formula:

where R ¹ and R ⁵ independently represent hydrogen, or hydrocarbyl, or substituted hydrocarbyl having from 1 to about 30 carbon atoms, R ⁴ represents hydrocarbyl or substituted hydrocarbyl having from about 1 to 30 carbon atoms, R ² in each of the groups x (R ² O) independently represents C ₂ -C ₄ alkylene; R ³ represents hydrogen or a straight or branched alkyl group having from 1 to about 30 carbon atoms; x independently represents an average of from 1 to about 60, and X ^- means an agriculturally acceptable anion.

In yet another embodiment, the present invention relates to a method for reducing the content of a surfactant in an aqueous composition of a herbicidal concentrate necessary to provide this degree of growth inhibition observed when the said composition is diluted with water and applied to the leaves of the plant. Said method comprises adding oxalic acid or a salt or ester thereof to the composition, wherein said composition comprises glyphosate or its salt or ester and one or more surfactants.

In another embodiment, the present invention relates to a method for reducing the aqueous toxicity of an aqueous herbicidal composition without reducing the degree of growth inhibition observed when the composition is diluted with water and applied to the leaves of the plant. The specified method involves the addition of oxalic acid or its salt or ester in the specified composition containing glyphosate or its salt or ester.

In another embodiment, the present invention relates to a method of inhibiting the growth of morning glory. The specified method involves applying the aqueous composition to the leaves of morning glory, where the specified composition contains glyphosate or its salt or ester and oxalic acid or its salt or ester.

In another embodiment, the present invention relates to an aqueous composition of a herbicidal concentrate containing glyphosate, a surfactant component and oxalic acid or its salt or ester, including:

(i) glyphosate or its salt or ester is present in solution in an aqueous medium at a concentration that is biologically effective when the composition is diluted in a suitable volume of water and applied to the leaves of a susceptible plant;

(ii) a surfactant component in the form of a solution or a stable suspension, emulsion or dispersion in said medium containing one or more surfactants; and

(iii) oxalic acid or its salt or ester.

The specified surfactant component includes at least one surfactant selected from cationogenic, nonionic and anionic surfactants.

In yet another embodiment, the present invention relates to a solid composition of a pesticidal concentrate containing a water-soluble pesticide and a compound that increases the permeability of the cell membrane. The specified pesticide is present in a concentration that is biologically effective in the dilution of the specified composition in a suitable volume of water with the formation of a mixture for applying enhanced action and applying this mixture to the leaves of a susceptible plant. A compound that increases the permeability of the cell membrane is a compound that enhances the cellular uptake of the pesticide by a plant treated with the indicated mixture for enhanced application compared to a plant treated with a standard mixture for the application that does not contain the specified compound, but otherwise having the same composition as the specified mixture for the application of enhanced action, where the mass ratio of the specified pesticide to the specified compound is at least 2.5: 1.

In another embodiment, the present invention relates to a solid composition of a herbicidal concentrate containing glyphosate and a compound that increases the permeability of the cell membrane. Glyphosate or a salt or ester thereof is present in a concentration that is biologically effective when the composition is diluted in a suitable volume of water to form a mixture for applying enhanced action and applying this mixture to the leaves of a susceptible plant. A compound that increases the permeability of the cell membrane in a plant is a compound that enhances the cellular uptake of the pesticide by a plant treated with the indicated mixture for application of enhanced action, compared with a plant treated with a standard mixture for application that does not contain the specified compound, but otherwise having such the same composition as the specified mixture for applying enhanced action.

In another embodiment, the present invention relates to a solid composition of a pesticidal concentrate containing a water-soluble pesticide, and a compound that suppresses oxidative burst. The specified pesticide is present in a concentration that is biologically effective when the composition is diluted in a suitable volume of water to form a mixture for application with enhanced action and application of this mixture to the leaves of a susceptible plant. A compound that suppresses an oxidative burst in plant cells is a compound that interferes with the protective response of a plant treated with the indicated enhanced mixture compared to a plant treated with a standard applied mixture that does not contain the compound, but otherwise has the same composition, like the specified mixture for the application of enhanced action, where the mass ratio of the specified pesticide to the specified compound is at least 2.5: 1.

In another embodiment, the present invention relates to a solid composition of a herbicidal concentrate comprising a glyphosate salt or ester and a compound that suppresses an oxidative flash. The glyphosate salt or ester is present in a concentration that is biologically effective when the composition is diluted in a suitable volume of water to form a mixture for enhanced application and application of this mixture to the leaves of a susceptible plant. A compound that suppresses an oxidative burst in plant cells is a compound that interferes with the protective response of a plant treated with the indicated enhanced mixture compared to a plant treated with a standard applied mixture that does not contain the compound, but otherwise has the same composition, as well as the specified mixture for applying enhanced action.

In another embodiment, the present invention relates to a solid composition of a pesticidal concentrate containing a water-soluble pesticide, and a compound that enhances the expression of hydroxyproline-rich glycoproteins. The specified pesticide is present in a concentration that is biologically effective in the dilution of the specified composition in a suitable volume of water with the formation of a mixture for applying enhanced action and applying this mixture to the leaves of a susceptible plant. A compound that enhances the expression of hydroxyproline-rich glycoproteins is a compound that increases the penetration of a pesticide into the phloem of a plant treated with the indicated enhanced application mixture compared to a plant treated with a standard application mixture that does not contain the specified compound but otherwise has such the same composition as the specified mixture for applying enhanced action, where the mass ratio of the specified pesticide to the specified compound is at least it least 2.5: 1.

In another embodiment, the present invention relates to a solid composition of a herbicidal concentrate containing a glyphosate salt or ester, and a compound that enhances the expression of hydroxyproline-rich glycoproteins. Glyphosate is present in a concentration that is biologically effective when the composition is diluted in a suitable volume of water to form a mixture for applying enhanced action and applying this mixture to the leaves of a susceptible plant. A compound that enhances the expression of hydroxyproline-rich glycoproteins is a compound that increases the penetration of a pesticide into the phloem of a plant treated with the indicated mixture for application of enhanced action compared to a plant treated with a standard mixture for application that does not contain the specified compound, but otherwise having the same composition, as well as the specified mixture for applying enhanced action.

In yet another embodiment, the present invention relates to a solid composition of a pesticidal concentrate containing a water-soluble pesticide and oxalic acid or its salt or ester. The specified pesticide is present in a concentration that is biologically effective in the dilution of the specified composition in a suitable volume of water with the formation of a mixture for applying enhanced action and applying this mixture to the leaves of a susceptible plant. The specified glyphosate and oxalic acid or its salt or ester are present in a mass ratio of at least 2.5: 1.

In another embodiment, the present invention relates to a solid composition of a pesticidal concentrate containing a glyphosate salt or ester and oxalic acid or a salt or ester thereof. Glyphosate is present in a concentration that is biologically effective in diluting the composition in a suitable volume of water and applying to the leaves of a susceptible plant.

And in a final embodiment, the present invention relates to a solid composition of a pesticidal concentrate containing a water-soluble pesticide, a surfactant and oxalic acid or a salt or ester thereof. The specified pesticide is present in a concentration that is biologically effective when the specified composition is diluted in a suitable volume of water and applied to the leaves of a susceptible plant. The surfactant component includes one or more cationogenic or nonionic surfactants.

DETAILED DESCRIPTION OF PREFERRED EMBODIMENTS

Some aqueous pesticidal concentrates, especially concentrates containing glyphosate potassium salt, do not combine well with surfactants. Therefore, it is desirable to minimize, and sometimes eliminate, surfactants from such compositions, since surfactants are quite expensive and in some cases cause water toxicity. It was found that the addition of oxalic acid or its salt or ester to glyphosate compositions increases the permeability of the cell membrane of plant cells or suppresses oxidative bursts with an increase in cellular absorption of glyphosate. This increase is not due to the ability of oxalic acid to form a chelate complex with calcium and other metal ions in hard water. Indeed, oxalic acid increases efficacy to a much greater extent than standard chelating agents such as EDTA or sodium citrate. Oxalic acid is more effective than EDTA, even when you consider that EDTA has a chelating ability, which is about five times higher than the chelating ability of oxalic acid. The addition of a relatively small amount of oxalic acid can significantly reduce the amount of surfactant necessary to obtain a stable composition, which, after dilution and application to the leaves of the plant, provides the desired suppression of plant growth. It also significantly increases the effectiveness of many surfactants, which give, to one degree or another, insufficient suppression of plant growth, which allows the use of a wider range of surfactants in herbicidal preparations. These compositions are effective in killing a wide range of broad-leaved plants, including Theophrastus, Crescent Astragalus and Ipomoea.

Without claiming to be a specific theory, we can say that there are probably several mechanisms by which oxalic acid or its salts or esters and other compounds increase the biological effectiveness of glyphosate. First, oxalic acid increases the permeability of the cell membrane in the plant by forming a chelate complex with calcium in the cell walls and / or in the apoplast and thereby inhibits the production of calcium-dependent protective responses. Secondly, increased expression of hydroxyproline-rich glycoproteins (HRGP) promotes glyphosate promotion in the phloem. Thirdly, oxalic acid inhibits oxidative burst in plant cells. An oxidative flash is a response expressed in early resistance produced by plant tissue, leading to regulation of the release of O ₂ ^- and hydrogen peroxide. In other words, oxalic acid inhibits the oxidation of free radicals directly or by blocking the signaling step (signaling step) leading to the activation of oxidase. Suppression of oxidative flare prevents the development of a protective response in plants, which to one degree or another limits the bioefficiency of glyphosate.

In one embodiment, the present invention relates to an aqueous pesticidal composition that comprises a water-soluble pesticide dissolved in water. This water-soluble pesticide is present in a concentration that is biologically effective when the composition is diluted in a suitable volume of water to form a mixture for applying enhanced action and applying this mixture to the leaves of a susceptible plant. The composition also includes a surfactant component in the form of a solution or a stable suspension, emulsion or dispersion in water. This surfactant component includes one or more surfactants. The surfactant component is present in a concentration sufficient to achieve acceptable thermal stability of the composition, such that the composition has a cloud point of at least about 50 ° C and a crystallization temperature not exceeding about 0 ° C. The composition also includes a compound that increases the permeability of the cell membrane in a plant with an increase in cellular uptake of the pesticide compared to a similarly loaded water-soluble pesticidal composition, which includes the same surfactant component without said compound.

In another embodiment, the aqueous pesticidal concentrate contains a pesticide, a surfactant component and a compound that suppresses oxidative burst in plant cells with increased cellular uptake of the pesticide, compared to a similarly loaded water-soluble pesticidal composition that includes the same surfactant component without the specified connection. Oxalic acid and its salts or esters in the compositions of the present invention are effective in increasing the permeability of the cell membrane and / or in suppressing oxidative burst.

Solid compositions of the pesticidal concentrate of the present invention include a pesticide and a compound that increases the permeability of the cell membrane in a plant or suppresses oxidative burst in plant cells with increased pesticide uptake by cells compared to a similarly loaded water-soluble pesticidal composition that includes the same surface-active component without said connections. A surfactant component is an optional component in said solid concentrate compositions. In some areas under the control of authorities, reminders of water toxicity or other environmental conditions, such as warning or caution labels, may be issued that indicate how much can be added and whether the surfactant can be added to solid concentrates of the present invention.

Although oxalic acid provides the greatest increase in the effectiveness of the compositions of the present invention, other components are also effective when incorporated into pesticidal compositions. To enhance the herbicidal efficacy, organic acids, in particular polycarboxylic acids, can be added to these compositions. Preferred polycarboxylic acids are dicarboxylic acids. Suitable dicarboxylic acids that can be added to these compositions are oxalic acid, malonic acid, succinic acid, glutaric acid, maleic acid, adipic acid and fumaric acid, their salts and mixtures, preferably with oxalic acid. Suitable salts are, for example, alkali metal salts such as sodium and potassium salts, alkanolamine salts and alkylamine salts such as IPA. Preferred salts are potassium oxalate, dipotassium oxalate, sodium oxalate, disodium oxalate, diammonium oxalate, diethanolaminoxalate, dimethylaminoxalate, oxanol acid alkanolamine salts and oxalic lower alkyl salts. The preparations contain such compounds in an amount sufficient to increase the increased effectiveness of the drug. Typically, in liquid systems, the mass ratio of all surfactants to the dicarboxylic acid compound can be from about 1: 1 to 50: 1, more preferably from about 5: 1 to 40: 1, and most preferably from about 5: 1 to 20: one. This ratio of the total amount of surfactants to the amount of dicarboxylic acid significantly increases the herbicidal efficacy of the resulting composition. It is preferable that the mass ratio of glyphosate in the form of free acid or in the form of its acid equivalent to carboxylic acid is from about 1: 1 to 500: 1, more preferably from about 2: 1 to 100: 1, and most preferably from about 2: 1 to 50: 1. In dry compositions, the weight ratio of all surfactants to carboxylic acid is from about 50: 1 to 1:30, more preferably from about 1: 1 to 5: 1, and most preferably from about 1: 1 to 3: 1.

The liquid concentrate compositions of the present invention preferably include a water-soluble herbicide in a concentration of about 20 to 45% by weight of the composition; a surfactant component in a concentration of about 0.1 to 25% by weight of said composition; and dicarboxylic acid in a concentration of about 0.01 to 20% by weight of the composition. More preferably, said compositions include glyphosate or a salt or ester thereof in a concentration of about 25 to 40% by weight of the composition, a surfactant in a concentration of about 0.1 to 20% by weight of the composition, and a dicarboxylic acid in a concentration of from about 0.01 to 15% by weight of the specified composition. Even more preferably, said compositions include glyphosate or a salt or ester thereof at a concentration of about 30 to 40% by weight of the composition, a surfactant component at a concentration of about 0.1 to 10% by weight of the composition, and dicarboxylic acid in a concentration of from about 0.01 to 10% by weight of the specified composition. Most preferably, said compositions include glyphosate or a salt or ester thereof in a concentration of about 31 to 40% by weight of the composition, a surfactant in a concentration of about 0.1 to 7% by weight of the composition, and oxal acid or its salt or ester in a concentration of from about 0.01 to 5% by weight of the specified composition.

The solid concentrate compositions of the present invention preferably include a water-soluble herbicide in a concentration of about 40 to 90% by weight of the composition, a surfactant in a concentration of up to about 30% by weight of the composition, and a dicarboxylic acid in a concentration of about 1 to 30% by weight of the specified composition. More preferably, said compositions include glyphosate or a salt or ester thereof in a concentration of about 50 to 80% by weight of the composition, a surfactant in a concentration of about 5 to 25% by weight of the composition, and dicarboxylic acid in a concentration of about 1 to 25% by weight of the composition. Even more preferably, said compositions comprise glyphosate or a salt or ester thereof in a concentration of about 60 to 80% by weight of said composition, a surfactant in a concentration of about 7.5 to 20% by weight of said composition, and dicarboxylic acid in a concentration of about 1 to 20% by weight of the specified composition. Most preferably, said compositions include glyphosate or a salt or ester thereof in a concentration of about 60 to 80% by weight of said composition, a surfactant in a concentration of about 7.5 to 25% by weight of said composition, and oxal acid or its salt or ester in a concentration of from about 5 to 20% by weight of the specified composition.

The compositions of the present invention have a viscosity of about no more than 1000 cP at 10 ° C, preferably about no more than 900 cP at 10 ° C, more preferably about no more than 800, 700, 600, 500, 400 or 300 cP at 10 ° C , and even more preferably, about no more than 200 cP at 10 ° C. at a shear rate of 45 / s.

As used herein, the term “water soluble” with respect to the herbicide or its salt or ester means that the solubility in deionized water at 20 ° C. is not less than about 50 g / l. Preferred water-soluble herbicides have a solubility in deionized water at 20 ° C of at least about 200 g / L. Particularly preferred water-soluble herbicides contain a herbicidally active acid or anionic moiety and are preferably present in the composition of the present invention in the form of one or more water-soluble salts. The aqueous phase of such a composition, in addition to the water-soluble herbicide, may contain, but not necessarily, other salts imparting ionic strength to said aqueous phase.

A particularly preferred group of water-soluble herbicides are herbicides, usually applied to the leaves of a plant after emergence. Although the present invention is not limited to any particular class of water-soluble herbicides applied to leaves, it has been found that the beneficial effect of the compounds depends, at least in part, on their herbicidal efficacy for systemic distribution in plants. Systemic distribution in a plant can occur along the apoplastic ("non-living") pathway, including xylem vessels and intercellular space, and in cell walls; along the symplastic (living) pathway, including phloem elements and other tissues, consisting of cells sympathetically connected by plasmodesma; either along the apoplastic and symplastic paths. For systemic herbicides applied to leaves, the most important route is the phloem, and it is obvious that the present invention has the greatest advantage in cases where a water-soluble herbicide spreads over the phloem. However, the compositions of the present invention can also be effective when the water-soluble herbicide is unsystematic, as is the case with paraquat.

Water-soluble herbicides suitable for use in the compositions of the present invention are acifluorfen, acrolein, amitrol, azulam, benazoline, bentazone, bialafos, bromacil, bromoxynil, chloramben, chloroacetic acid, clopyralide, 2,4-D, 2,4-DB, dalon , dicamba, dichlorprop, difenzoquat, diquat, endothall, fenac, fenoxaprop, flamprop, flumiclorac, ftorglikofen, flupropanate, fomesafen, fozamin, glufosinate, glyphosate, imazamet, imazamethabenz, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, ioxynil, MCPA, MCPB , mecoprop, methylarso new acid, naphthalam, nonanoic acid, paraquat, picloram, hinklorac, sulfamic acid, 2,3,6-TBA, TCA, triclopyr and their water-soluble salts.

Preferred herbicides propagating throughout the phloem for use in the compositions of the present invention include, but are not limited to, aminotriazole, azulam, bialaphos, clopyralid, dicamba, glufosinate, glyphosate, imidazolinones, such as imazamet, imazametabenz, imazamox, imaziapaz, imazapaz, imazetapyr; phenoxides such as 2,4-D, 2,4-DB, dichloroprop, MCPA, MCPB and mecoprop, picloram and triclopyr. A particularly preferred group of water-soluble herbicides are the salts of bialaphos, glufosinate and glyphosate. Another particularly preferred group of water soluble herbicides are salts of imidazolinone herbicides.

The compounds of the present invention may contain, but not necessarily, more than one water-soluble herbicide in solution in the aqueous phase.

A particularly preferred water-soluble herbicide used in the composition of the present invention is glyphosate, the acid form of which is alternatively known as N- (phosphonomethyl) glycine. Thus, for example, glyphosate salts used in the compositions of the present invention are described in US Pat. ; ammonium salt; salts of C _1-6 alkylammonium, for example dimethylammonium and isopropylammonium; C _1-6 alkanolammonium salts, for example monoethanolammonium; salts of C _1-6 alkylsulfonium, for example trimethylsulfonium; and mixtures thereof. The N-phosphonomethylglycine molecule contains three acid groups having different pKa values; therefore, mono-, di- and tribasic salts, or any mixtures thereof, or salts of any intermediate level of neutralization, respectively, can be used. Particularly preferred glyphosate salts are potassium salt, isopropylamine salt, ammonium salt, diammonium salt, monoethanolamine salt and trimethylsulfonium salt. Most preferred is potassium salt.

The relative amount of glyphosate potassium salt loaded into the pesticidal composition of the present invention can vary widely depending on many factors, including the surfactant system used, the rheological properties of the composition, and the temperature range at which the composition is used. The glyphosate potassium salt in the herbicidal compositions of the present invention is preferably at least 320 g ke / l, and more preferably at least 330, 340, 350, 360, 370, 380, 390, 400, 410, 420, 430, 440, 450, 460, 470, 480, 490, 500, 510, 520, 530, 540, 550, 560, 570, 580, 590, 600, 610, 620, 630, 640, 650, 660, 670, 680, 690 or 700 grams ke / l.

The compositions of the present invention may contain, but not necessarily, one or more water-soluble herbicides in solution in an organic solvent or in suspension in a concentration that is biologically effective when the composition is diluted in a suitable volume of water and applied to the leaves of a susceptible plant. A preferred water-soluble herbicide is selected from the group consisting of acetochlor, aclonifen, alachlor, ametrine, amidosulfuron, anilofos, atrazine, azaphenidine, azimsulfuron, benfluuralin, benfuresate, benzenulfurfenum, benzofenfen benfam benfen benzenfen benzene , butralin, butroxidime, butylate, kafenstrol, carfentrazone ethyl, carbetamide, chlorobromuron, chloridazone, chlorimuron ethyl, chlorotoluron, chloronitrophene, chlorotoluron, chlorprofam, chlorosulfuron, chlorine l-dimethyl, chlorothiamide, cinidone-ethyl, cinmethyline, cinosulfuron, cododyme, clodinafop-propargyl, clomazone, clomeprop, cloransulam-methyl, cyanazine, cycloate, cyclosulfamuron, cycloxydime, cygalofop-butamidefenimel desimedimedimide methyl, diflufenican, dimefuron, dimepiperate, dimethachlor, dimetamethrin, dimethenamide, dinitramine, dinoterb, diphenamide, dithiopyr, diuron, ERTS, esprocarb, etalfluralin, etametsulfuron-methyl, etofisenofenofenofenofenofenofenofenofenofenofenofozena-etofisanofenofozenaponis etofumanose , phenuron, flamprop-methyl, flazasulfuron, fluazifop-butyl, fluazifop-R-butyl, fluazoate, fluchloralin, flumetsulam, flumiclorocentyl, flumioxazine, fluomethuron, fluorochloridorone, flupoxam fluluperluflumeluflam fluluperluflumeluflam fluluperluflumeluflam fluluperluflumeluflam fluluperluflumeluflam fluluperluflumeluflam fluluperluflumeluflam fluluperluflumeluflam fluluperlumethlufluurflumeluflam fluluperluflumeluflametluurlufluurflumeluflapheluflam fluluperluflumethluurflumethlufluoromelt -methyl, graminicides, halosulfuron, haloxifop, hexazinone, imazosulfuron, indanofan, isoproturon, isouron, isoxaben, isoxaflutol, isoxapyrifif, lenacyl, linuron, mefenacet, metamitron, metazenzoumouron, methazenzuurone, methazenzuurone, methazenzuurone, methazenzuurone, methazenzouroone, romuron, metolachlor, S-metolachlor, metosulam, methoxuron, metribucin, metsulfuron, molinate, monolinuron, naproanilide, napropamide, neburon, nicosulfuron, norflurazone, orbencarb, oryzaline, oxadiabenazonazonazoneazonazonazoneazonazoneazonazonazonazoneazona ponaazonazonazonaazona-azona-azona-azona-azona-azonazonazonazoneazona-azona-azona-azona-azona-azona-azona-azona-azona-azona-azona-azona-azona-azona-azona-azona-azona-azona-azonesonazones piperophos, pretilachlor, primisulfuron, prodiamine, profluazole, promethone, promethrin, propachlor, propanil, propachisafop, propazin, profam, propisochlor, propisamide, prosulfocarb, prosulfuron, pyroflufen-ethyl, pyr azogil, pyrazolinate, pyrazosulfuron-ethyl, pyrazoxifene, pyributicarb, pyridate, pyriminobac-methyl, hinklorac, hinmerak, hizalofop, hizalofop-R, rimsulfuron, setoksidim, siduron, simazin, simethrin sulfuronuron, sulonononoton, sulfotononot terapraloxydim, terbacyl, terbumeton, terbutylazine, terbutrin, tenichlor, thiazopir, thidiazimine, tifensulfuron, thiobencarb, thiocarbazil, tralcoxidime, triallate, triasulfuron, tribenuron, trietazine, trifluralin, and on vernolate.

The surface-active component of the composition of the present invention, when administered together with the aforementioned herbicidal components of the present invention, is a component of a certain type and is present in a concentration sufficient for the cell to absorb the herbicide by the plant and to transfer the herbicidally effective amount of glyphosate. This can be achieved by one of the methods, which provides closer contact between the applied herbicidal composition and the microtopographically coarse surface of a given plant, for example, by smoothing the contact angle of the composition so that this penetrates the cracks and pores of the given plant. So, for example, a composition containing surfactants should also preferably enhance adhesion or adhesion to the surface of the plant when it is used in an aqueous solution, and this should not prevent the solution from drying out over a certain period of time, which is sufficient for the penetration of this composition.

It has been found that various surfactants are effective for the preparation of the herbicidal compositions and concentrates of the present invention, and in particular for the preparation of herbicidal compositions and concentrates containing the glyphosate potassium salt.

Cationic surfactants effective for preparing herbicidal compositions are:

(a) an aminated alkoxylated alcohol having the formula:

or

where R ¹ represents hydrogen or hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms; R ² in each of the groups x (R ² O) and y (R ² O) independently represents C ₂ -C ₄ alkylene; each of R ³ and R ⁶ independently represents hydrocarbylene or substituted hydrocarbylene having from 1 to about 6 carbon atoms; R ⁴ represents hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, hydroxy-substituted hydrocarbyl, - (R ⁶ ) _n (R ² O) _y R ⁷ , -C (= NR ¹¹ ) NR ¹² R ¹³ , - C (= O) NR ¹² R ¹³ , —C (= S) NR ¹² R ¹³ , or R ⁴ together with R ⁵ and the nitrogen atom to which they are attached form a cyclic or heterocyclic ring; R ⁵ represents hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, hydroxy-substituted hydrocarbyl, - (R ⁶ ) _n - (R ² O) _y R ⁷ , —C (= NR ¹¹ ) NR ¹² R ¹³ , —C (= O) NR ¹² R ¹³ , —C (= S) NR ¹² R ¹³ , or R ⁵ together with R ⁴ and the nitrogen atom to which they are attached form a cyclic or heterocyclic ring; R ⁷ represents hydrogen or a straight or branched alkyl group having from 1 to about 4 carbon atoms; R ¹¹ , R ¹² and R ¹³ represent hydrogen, hydrocarbyl or substituted hydrocarbyl; R ¹⁴ represents hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, hydroxy-substituted hydrocarbyl, - (R ⁶ ) _n - (R ² O) _y R ⁷ , -C (= NR ¹¹ ) NR ¹² R ¹³ , -C (= O) NR ¹² R ¹³ or -C (= S) NR ¹² R ^13, n is 0 or 1, x and y are independently an average number from 1 to about 60, and a ^- is an agriculturally acceptable anion. In this context, preferred hydrocarbyl (hydrocarbylene) groups R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ¹¹ , R ¹² and R ¹³ are straight or branched alkyl (alkylene), straight or branched alkenyl (alkenylene), straight or branched alkynyl (alkynylene), aryl (arylene) or aralkyl (aralkylene) groups. In one embodiment, R ³ is straight alkylene, preferably ethylene, and R ¹ , R ² , R ⁴ and R ⁵ are as defined above. In another embodiment, R ⁴ is H, alkyl, or —R ² OR ⁷ , and R ¹ , R ² , R ³ , R ^5, and R ⁷ are as defined above. In yet another embodiment, R ¹ represents a straight or branched alkyl or straight or branched alkenyl group having from about 8 to 25 carbon atoms. R ² in each of the groups x (R ⁷ O) independently represents C ₂ -C ₄ alkylene, R ³ represents a straight or branched alkylene group having from 1 to about 6 carbon atoms, each of R ⁴ and R ⁵ independently represents hydrogen or a straight or branched alkyl group having from 1 to about 6 carbon atoms, and x represents an average of from 1 to about 30. More preferably, R ¹ represents a straight or branched alkyl group having from about 12 to 22 carbon atoms. R ² in each of the groups x (R ⁷ O) independently represents ethylene or propylene, R ³ represents a straight or branched alkylene group having from 1 to about 4 carbon atoms, each of R ⁴ and R ⁵ independently represents hydrogen, methyl or tris (hydroxymethyl) methyl, and x represents an average of about 2 to 30. Even more preferably, R ¹ represents a straight or branched alkyl group having from about 12 to 18 carbon atoms, R ² in each of the groups x (R ² O) independently is ethylene or propylene, R ³ is ethylene or 2-w roksipropilenovuyu group, each of R ⁴ and R ⁵ independently represent hydrogen or methyl, and x is an average number from about 4 to 20. Most preferably R ¹ represents a straight or branched alkyl group having from about 12 to 18 carbon atoms, R ² in each of the groups x (R ² O) independently represents ethylene or propylene, R ³ represents an ethylene or 2-hydroxypropylene group, R ⁴ and R ⁵ represent methyl, and x represents an average of about 4 to 20. The compound of formula (10) has preferred groups described above, and R ¹⁴ preferably represents hydrogen or a straight or branched alkyl or alkenyl group, more preferably an alkyl, and most preferably a methyl group. Preferred monoalkoxylated amines are PEG (13) - or PEG (18) -C _14-15 ether-propylamines and PEG (7,10,15 or 20) -C _16-18- ether-propylamines (from Tomah) or PEG (13) - or PEG (18) -C _14-15- esterodimethylpropylamines and PEG (10.15 or 20 or 25) -C _16-18- esterodimethylpropylamines (from Tomah).

(b) hydroxylated amides having the formula:

where R ¹ is hydrocarbyl or substituted hydrocarbyl having from about 4 to 30 carbon atoms, R ² is hydrogen or hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, and R ³ is hydroxyalkyl, polyhydroxyalkyl or poly (hydroxyalkyl) alkyl . In this context, preferred hydrocarbyl groups R ¹ and R ² are straight or branched alkyl, straight or branched alkenyl, straight or branched alkynyl, aryl or aralkyl groups. Preferably, the hydroxylated amides have the formula:

where R ¹ represents hydrocarbyl or substituted hydrocarbyl having from about 4 to 30 carbon atoms, R ³ represents hydrogen or hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, and n is from 1 to about 8. In this context, preferred hydrocarbyl groups R ¹ and R ² are straight or branched alkyl, straight or branched alkenyl, straight or branched alkynyl, aryl or aralkyl groups. Preferably R ¹ represents a straight or branched alkyl or straight or branched alkenyl group having from about 8 to 30 carbon atoms; R ² represents hydrogen, a straight or branched alkyl or straight or branched alkenyl group having from 1 to about 30 carbon atoms, and n is about 4-8; or R ¹ and R ² independently represent a straight or branched alkyl group or a straight or branched alkenyl group having from about 4 to 30 carbon atoms, and n is about 4-8. More preferably, R ¹ represents a straight or branched alkyl or straight or branched alkenyl group having from about 8 to 22 carbon atoms; R ² represents hydrogen, a straight or branched alkyl or straight or branched alkenyl group having from 1 to about 6 carbon atoms, and n is about 4-8; or R ¹ and R ² independently represent a straight or branched alkyl or straight or branched alkenyl group having about 4 to 8 carbon atoms, and n is about 4-8.

(c) diamines having the formula:

where R ¹ , R ² and R ⁵ independently represent hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, or —R ⁸ (OR ⁹ ) _n OR ¹⁰ ; R ³ represents hydrocarbylene or substituted hydrocarbylene having from 2 to about 18 carbon atoms, R ⁸ and R ⁹ separately represent hydrocarbylene or substituted hydrocarbylene having from 2 to about 4 carbon atoms, R ⁴ and R ¹⁰ independently represent hydrogen or hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, m is 0 or 1, n is an average of 0 to about 40, and X is —C (O) or —SO ₂ . In this context, preferred hydrocarbyl (hydrocarbylene) groups R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ¹⁰ are straight or branched alkyl (alkylene), straight or branched alkenyl (alkenylene), straight or branched alkynyl (alkynylene) , aryl (arylene) or aralkyl (aralkylene) groups. Preferably, R ¹ , R ² , R ⁴ and R ⁵ independently represent hydrogen or a straight or branched alkyl or alkenyl group having from 1 to about 6 carbon atoms, and R ³ represents a straight or branched alkylene group having from 2 to about 6 atoms carbon. More preferably, R ¹ , R ² , R ⁴ and R ⁵ independently represent hydrogen or a straight or branched alkyl group having from 1 to about 6 carbon atoms, and R ³ represents straight or branched alkylene having from 2 to about 6 carbon atoms. Most preferably, R ¹ , R ² , R ⁴ and R ⁵ independently represent hydrogen or methyl, and R ³ represents ethylene or propylene.

(d) mono- or diammonium salts having the formulas:

or

where R ¹ , R ² , R ⁴ , R ⁵ and R ⁷ independently represent hydrogen or hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, or —R ⁸ (OR ⁹ ) _n OR ¹⁰ ; R ⁶ is hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, R ³ is hydrocarbylene or substituted hydrocarbylene having from 2 to about 30 carbon atoms, R ⁸ and R ^{9 are} individually hydrocarbylene or substituted hydrocarbylene having from 2 to about 4 carbon atoms, R ¹⁰ represents hydrogen or hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, m is 0 or 1, n is an average of 0 to about 40, X is —C (O) or —SO ₂ ; Z represents —C (O) -, and A ^- represents an agriculturally acceptable anion. In this context, preferred hydrocarbyl (hydrocarbylene) groups R ¹ -R ¹⁰ are straight or branched alkyl (alkylene), straight or branched alkenyl (alkenylene), straight or branched alkynyl (alkylene), aryl (arylene) or aralkyl (aralkylene) groups. Preferably R ¹ , R ² , R ⁴ , R ⁵ and R ⁷ independently represent hydrogen or a straight or branched alkyl or alkenyl group having from 1 to about 6 carbon atoms, R ⁶ represents a straight or branched alkyl or alkenyl group having from about 8 to 30 carbon atoms, m is 0 or 1, and R ³ is straight or branched alkylene having from 2 to about 22 carbon atoms. More preferably, R ¹ , R ² , R ⁴ , R ⁵ and R ⁷ independently represent hydrogen or a straight or branched alkyl group having from 1 to about 6 carbon atoms, R ⁶ represents a straight or branched alkyl group having from about 8 to 22 carbon atoms, m is 0 or 1, and R ³ is straight or branched alkylene having from 2 to about 20 carbon atoms. Most preferably, R ¹ , R ² , R ⁴ , R ⁵ and R ⁷ independently represent hydrogen or methyl, R ⁶ represents a straight or branched alkyl group having from about 8 to 18 carbon atoms, m is 0 or 1, and R ³ represents ethylene or propylene.

(e) poly (hydroxyalkyl) amines having the formula:

or

where R ¹ represents hydrocarbyl or substituted hydrocarbyl having from about 4 to 30 carbon atoms or -R ⁴ OR ⁸ , R ² represents hydrogen or hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms; R ³ is hydroxyalkyl, polyhydroxyalkyl or poly (hydroxyalkyl) alkyl; R ⁴ represents hydrocarbylene or substituted hydrocarbylene having from 2 to about 18 carbon atoms, R ⁸ represents hydrogen, or hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms; R ⁵ represents - (R ⁶ O) _y R ⁷ ; R ⁶ in each of the y groups (R ⁶ O) independently represents C ₂ -C ₄ alkylene; R ⁷ represents hydrogen or a straight or branched alkyl group having from 1 to about 4 carbon atoms, and y represents an average of from 0 to about 30. Preferably, the poly (hydroxyalkyl) amines have the formula:

or

where R ¹ represents hydrocarbyl or substituted hydrocarbyl having from about 4 to 30 carbon atoms or -R ³ OR ⁴ , R ² represents hydrogen or hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms; R ³ is hydrocarbylene or substituted hydrocarbylene having from about 2 to 18 carbon atoms; R ⁴ represents hydrogen, or hydrocarbyl, or substituted hydrocarbyl having from 1 to about 30 carbon atoms: m and n independently represent integers from 0 to about 7, while the sum of m and n does not exceed about 7, and p represents an integer from about 1 to 8. In this context, preferred hydrocarbyl (hydrocarbylene) groups R ¹ , R ² , R ³ and R ⁴ are straight or branched alkyl (alkylene), straight or branched alkenyl (alkenylene), straight or branched alkynyl (alkynylene) aryl (arylene) or an aralkyl (aralkylene) group. Preferably R ¹ represents a straight or branched alkyl or straight or branched alkenyl group having from about 8 to 30 carbon atoms or —R ³ OR ⁴ , R ² represents hydrogen or a straight or branched alkyl group or a straight or branched alkenyl group having from 1 up to about 30 carbon atoms, R ³ represents a straight or branched alkylene or alkenylene group having from 2 to about 6 carbon atoms, R ⁴ represents a straight or branched alkyl or alkenyl group having from 8 to 22 carbon atoms, m and n independently represent integers from 0 to about 7; wherein the sum of m and n is about 3-7, and p is an integer from 4 to about 8; or R ¹ and R ² independently represent a straight or branched alkyl group or a straight or branched alkenyl group having from about 4 to 30 carbon atoms, m and n independently represent integers from 0 to about 7; wherein the sum of m and n is about 3-7, and p is an integer from about 4 to 8. More preferably, R ¹ represents a straight or branched alkyl or straight or branched alkenyl group having from about 8 to 22 carbon atoms or —R ³ OR ⁴ , R ² represents hydrogen or a straight or branched alkyl group or a straight or branched alkenyl group having from 1 to about 6 carbon atoms, R ³ represents a straight or branched alkylene or alkenylene group having from 2 to about 6 carbon atoms, R ⁴ Pres is a straight or branched alkyl or alkenyl group having from about 8 to 18 carbon atoms, m and n independently represent integers from 0 to about 7; wherein the sum of m and n is from about 3 to 7, and p is an integer from about 4 to 8; or R ¹ and R ² independently represent straight or branched alkyl or straight or branched alkenyl groups having from about 4 to 8 carbon atoms; m and n independently represent integers from 0 to about 7; wherein the sum of m and n is from about 3 to 7, and p is an integer from about 4 to 8. Even more preferably, R ¹ represents a straight or branched alkyl group having from about 8 to 18 carbon atoms or —R ³ OR ⁴ , R ² represents hydrogen or methyl, and m and n independently represent integers from 0 to about 4, R ³ represents a straight or branched alkylene group having from 2 to about 6 carbon atoms, R ⁴ represents a straight or branched alkyl group having from about 8 to 18 carbon atoms, the sum of m and n is approximately 4 and p is an integer of about 4. Most preferably, R ¹ represents a straight or branched alkyl group having from about 8 to 18 carbon atoms or —R ³ OR ⁴ , R ² represents methyl, R ³ represents ethylene, propylene, hydroxyethylene or 2-hydroxypropylene, R ⁴ represents a straight or branched alkyl group having from about 8 to 18 carbon atoms, and m and n independently represent integers from 0 to about 4, the sum of m and n is about 4, and p is an integer of about 4. These compounds are commercially available and supplied by Aldrich and Clariant.

(f) alkoxylated poly (hydroxyalkyl) amines having the formula:

where R ¹ and R ³ independently represent hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, R ² in each of the groups x (R ² O) independently represents C ₂ -C ₄ alkylene; R ⁴ is hydrocarbylene or substituted hydrocarbylene having from 1 to about 30 carbon atoms, R ⁵ is hydroxyalkyl, polyhydroxyalkyl or poly (hydroxyalkyl) alkyl; x represents an average of from 0 to about 30; and y represents 0 or 1. In this context, preferred hydrocarbyl (hydrocarbylene) groups R ¹ , R ³ and R ⁴ are straight or branched alkyl (alkylene), straight or branched alkenyl (alkenylene), straight or branched alkynyl (alkylene), aryl (arylene) or aralkyl (aralkylene) groups. Preferred alkoxylated poly (hydroxyalkyl) amines have the formula:

or

where R ¹ and R ³ independently represent hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, R ² in each of the groups x (R ² O) independently represents C ₂ -C ₄ alkylene; R ⁴ is hydrocarbylene or substituted hydrocarbylene having from 1 to about 30 carbon atoms, m and n independently represent integers from about 0 to 7, the sum of m and n does not exceed about 7, and p is an integer from 1 to about 8, x represents an average of 0 to about 30, and y is 0 or 1. In this context, preferred hydrocarbyl (hydrocarbylene) groups R ¹ , R ³ and R ⁴ are straight or branched alkyl (alkylene), straight or branched alkenyl (alkenylene) ), straight or branched alkynyl (a quinylene), aryl (arylene) or aralkyl (aralkylene) groups. Preferably R ¹ represents a straight or branched alkyl or straight or branched alkenyl group having from about 8 to 30 carbon atoms; R ² in each of the groups x (R ² O) independently represents C ₂ -C ₄ alkylene; R ³ represents hydrogen or a straight or branched alkyl group or a straight or branched alkenyl group having from 1 to about 30 carbon atoms; R ⁴ represents straight or branched alkylene having from 1 to about 30 carbon atoms, m and n independently represent integers from 0 to about 7; wherein the sum of m and n is from about 3 to 7, p is an integer from 1 to about 8, x is an average from 0 to about 30, and y is 0 or 1. More preferably, R ¹ represents a straight or branched alkyl group having about 8 to 22 carbon atoms, R ² in each of the x (R ² O) groups independently represents ethylene or propylene, R ³ represents hydrogen or a straight or branched alkyl group having from 1 to about 6 carbon atoms, R ⁴ represents a straight or branched alkylene having from 1 to about 6 carbon atoms, m and n represent integers from 0 to about 7, the sum of m and n is from about 3 to 7, p is an integer from 1 to about 8, x is an average from 0 to about 30, and y is 0 or 1. Most preferably R ¹ represents a straight or branched alkyl group having from about 8 to 18 carbon atoms, R ² in each of the x (R ² O) groups independently represents ethylene or propylene, R ³ represents hydrogen or methyl, m and n independently represent integers from 0 to about 7, the sum of m and n is from about 3 to 7, p is an integer from 1 to about 8, x p aven to an average of 0 to about 30, and y is 0.

(g) di-poly (hydroxyalkyl) amine having the formula:

where R ¹ and R ³ independently represent hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 22 carbon atoms, R ² is hydrocarbylene or substituted hydrocarbyl having from 2 to about 18 carbon atoms, and R ⁴ and R ⁵ are hydroxyalkyl, polyhydroxyalkyl or poly (hydroxyalkyl) alkyl. In this context, preferred hydrocarbyl (hydrocarbylene) groups R ¹ , R ² and R ³ are straight or branched alkyl (alkylene), straight or branched alkenyl (alkenylene), straight or branched alkynyl (alkylene), aryl (arylene) or aralkyl (aralkylene) ) groups. A preferred di-poly (hydroxyalkyl) amine has the formula:

where R ¹ and R ³ independently represent hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 22 carbon atoms, R ² represents hydrocarbylene or substituted hydrocarbyl having from 2 to about 18 carbon atoms, and m and n independently represent integers from 1 to 8. In this context, preferred hydrocarbyl (hydrocarbylene) groups R ^1, R ² and R ³ represent straight or branched alkyl (alkylene), linear or branched alkenyl (alkenylene), linear or branched alkynyl (alkynyl oic), aryl (arylene), or aralkyl (aralkylene) groups. Preferably, R ¹ and R ³ independently represent hydrogen or a straight or branched alkyl group having from 1 to about 18 carbon atoms, R ² represents a straight or branched alkylene or straight or branched alkenylene group having from 2 to about 18 carbon atoms, and m and n independently represent integers from about 1 to 8. More preferably, R ¹ and R ³ independently represent hydrogen or a straight or branched alkyl group having from 6 to about 12 carbon atoms, R ² represents a straight or branched an alkylene group having from 2 to about 6 carbon atoms, and m and n independently represent integers from about 4 to 8; or R ¹ and R ³ independently represent hydrogen or a straight or branched alkyl group having from 1 to about 4 carbon atoms, R ² represents a straight or branched alkylene group having from 2 to about 16 carbon atoms, and m and n independently represent whole numbers from about 4 to 8. Most preferably, R ¹ and R ³ independently represent hydrogen or a straight or branched alkyl group having from 6 to about 12 carbon atoms, R ² represents ethylene or propylene, and m and n independently represent integers from about four up to 8; or R ¹ and R ³ independently represent hydrogen or a straight or branched alkyl group having from 1 to about 4 carbon atoms, R ² represents a straight or branched alkylene group having from 2 to about 12 carbon atoms, and m and n independently represent whole numbers from about 4 to 8.

(h) Quaternary poly (hydroxyalkyl) amine salts having the formula:

where R ¹ represents hydrocarbyl or substituted hydrocarbyl having from about 4 to 30 carbon atoms, R ² and R ³ independently represent hydrogen or hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, R ⁴ is hydroxyalkyl, polyhydroxyalkyl or poly ( hydroxyalkyl) alkyl; and X ^- is an agriculturally acceptable anion. In this context, preferred hydrocarbyl groups R ¹ , R ² and R ³ are straight or branched alkyl, straight or branched alkenyl, straight or branched alkynyl, aryl or aralkyl groups. Preferred salts of the Quaternary poly (hydroxyalkyl) amine have the formula:

or

where R ¹ represents —X _m - (R ⁴ O) _y R ⁵ , hydrocarbyl or substituted hydrocarbyl having from about 4 to 30 carbon atoms; R ² and R ³ independently represent hydrogen or hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, m and n independently represent integers from 0 to about 7, the sum of m and n does not exceed about 7, p is an integer from 1 to about 8, X ^- represents an agriculturally acceptable anion, R ⁴ in each of the y (R ⁴ O) groups independently represents C ₂ -C ₄ alkylene; R ⁵ represents hydrogen or a straight or branched alkyl group having from 1 to about 4 carbon atoms, X represents hydrocarbylene or substituted hydrocarbylene having from 2 to about 18 carbon atoms, m is 0 or 1, and y is an average of 0 to about 30. In this context, preferred hydrocarbyl groups R ¹ , R ² and R ³ are straight or branched alkyl, straight or branched alkenyl, straight or branched alkynyl, aryl or aralkyl groups. Preferably R ¹ represents a straight or branched alkyl or straight or branched alkenyl group having from about 8 to 30 carbon atoms, R ² and R ³ independently represent hydrogen or a straight or branched alkyl or straight or branched alkenyl group having from 1 to about 30 carbon atoms, m and n independently represent integers from 0 to about 7, the sum of m and n is from about 3 to 7, and p is an integer from about 4 to 8; or R ¹ , R ² and R ³ independently represent a straight or branched alkyl or straight or branched alkenyl group having from about 4 to 30 carbon atoms, and m and n independently represent integers from 0 to about 7, the sum of m and n is not exceeds about 7, and p is an integer from about 4 to 8. More preferably, R ¹ represents a straight or branched alkyl or straight or branched alkenyl group having from about 8 to 22 carbon atoms, R ² and R ³ independently represent hydrogen or direct or branched alkyl or a straight or branched alkenyl group having from 1 to about 6 carbon atoms, m and n independently represent integers from 0 to about 7, the sum of m and n is from about 3 to 7, and p is an integer from about 4 to 8; or R ¹ , R ² and R ³ independently represent a straight or branched alkyl or straight or branched alkenyl group having from about 4 to 8 carbon atoms, m and n independently represent integers from 0 to about 7, the sum of m and n is approximately 3-7, and p is an integer from about 4 to 8. Even more preferably, R ¹ represents a straight or branched alkyl group having from about 8 to 18 carbon atoms, R ² and R ³ independently represent hydrogen or methyl, m and n independently represent integers from 0 to about 4, the sum of m and n is about 4, and p is an integer of about 4. Most preferably, R ¹ represents a straight or branched alkyl group having from about 8 to 18 carbon atoms, R ² and R ³ independently represent methyl, m and n independently represent integers from 0 to about 4, the sum of m and n is about 4, and p is an integer of about 4.

(i) triamines having the formula:

where R ¹ represents hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms; R ² , R ³ , R ⁴ and R ⁵ independently represent hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, or - (R ⁸ ) _s (R ⁷ O) _n R ⁶ ; R ⁶ represents hydrogen or a straight or branched alkyl group having from 1 to about 4 carbon atoms; R ⁷ in each of the groups n (R ⁷ O) independently represents C ₂ -C ₄ alkylene; R ⁸ represents hydrocarbylene or substituted hydrocarbylene having from 1 to about 6 carbon atoms, n represents an average of 1 to about 10, s represents 0 or 1, and x and y independently represent an integer from 1 to about 4. In this context preferred hydrocarbyl (hydrocarbylene) groups R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁸ are straight or branched alkyl (alkylene), straight or branched alkenyl (alkenylene), straight or branched alkynyl (alkylene), aryl ( arylene) or aralkyl (macaw kilenovuyu) group. Preferably R ¹ represents a straight or branched alkyl or straight or branched alkenyl group having from about 8 to 30 carbon atoms, R ² , R ³ , R ⁴ and R ⁵ independently represent hydrogen or a straight or branched alkyl or straight or branched alkenyl group, having from 1 to about 30 carbon atoms, or - (R ⁷ O) _n R ⁶ ; R ⁶ represents hydrogen, methyl or ethyl; R ⁷ in each of the groups n (R ⁷ O) independently represents C ₂ -C ₄ alkylene; n is an average number from 1 to about 10, and x and y independently represent integers from 1 to about 4. More preferably, R ¹ represents a straight or branched alkyl group having from about 8 to 18 carbon atoms, R ² , R ³ , R ⁴ and R ⁵ independently represent hydrogen, a straight or branched alkyl group having from 1 to about 6 carbon atoms, or - (R ⁷ O) _n R ⁶ ; R ⁶ represents hydrogen or methyl; R ⁷ in each of the groups n (R ⁷ O) independently represents ethylene or propylene; n is an average number from 1 to about 5, and x and y independently represent integers from about 1 to 4. Most preferably, R ¹ represents a straight or branched alkyl group having from about 8 to 18 carbon atoms, R ² , R ³ , R ⁴ and R ⁵ independently represent hydrogen or - (R ⁷ O) _n R ⁶ ; R ⁶ represents hydrogen; R ⁷ in each of the groups n (R ⁷ O) independently represents ethylene or propylene; n is an average of from 1 to about 5, and x and y independently represent integers from 1 to about 4. Acros and Clariant Genamin 3119 are commercially available triamines.

(j) diamines having the formula:

where R ¹ , R ³ , R ⁴ and R ⁵ independently represent hydrogen or hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, or - (R ⁸ O) _x R ⁷ ; R ² is hydrocarbylene or substituted hydrocarbylene having from 2 to about 30 carbon atoms, —C (= NR ¹¹ ) NR ¹² R ¹³ , —C (= O) NR ¹² R ¹³ , —C (= S) NR ¹² R ¹³ , -C (= NR ¹² ) -, -C (S) - or -C (O) -; R ⁶ in each of the groups x (R ⁶ O) and y (R ⁶ O) independently represents C ₂ -C ₄ alkylene; R ⁷ represents hydrogen or a straight or branched alkyl group having from 1 to about 30 carbon atoms; R ¹¹ , R ¹² and R ¹³ represent hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, x represents an average of from 1 to about 50, and y represents an average of from 0 to about 60. In this context, preferred hydrocarbyl (hydrocarbylene) groups R ¹ , R ² , R ³ , R ⁴ and R ⁵ are straight or branched alkyl (alkylene), straight or branched alkenyl (alkenylene), straight or branched alkynyl (alkylene), aryl (arylene) or aralkyl (aralkylene) group. Preferably, R ¹ , R ³ , R ⁴ and R ⁵ independently represent hydrogen or a straight or branched alkyl or straight or branched alkenyl group having from about 1 to 22 carbon atoms or - (R ⁶ O) _x R ⁷ ; R ² represents a straight or branched alkylene or straight or branched alkenylene group having from 1 to about 6 carbon atoms; R ⁶ in each of the groups x (R ⁶ O) and y (R ⁶ O) independently represents C ₂ -C ₄ alkylene; R ⁷ represents hydrogen or a straight or branched alkyl group having from 1 to about 4 carbon atoms; x represents an average of from 1 to about 30, and y represents an average of from 0 to about 60. More preferably, R ¹ , R ³ , R ⁴ and R ⁵ independently represent hydrogen or a straight or branched alkyl group having from about 1 to 18 carbon atoms or - (R ⁶ O) _x R ⁷ ; R ² represents a straight or branched alkylene group having from about 1 to 6 carbon atoms; R ⁶ in each of the groups x (R ⁶ O) and y (R ⁶ O) independently represents ethylene or propylene; R ⁷ represents hydrogen or a straight or branched alkyl group having from 1 to about 4 carbon atoms; x represents an average of from 1 to about 15, and y represents an average of from 0 to about 60. Most preferably, R ¹ and R ³ independently represent straight or branched alkyl groups having from about 8 to 18 carbon atoms; and R ⁴ and R ⁵ independently represent hydrogen; R ² represents a straight or branched alkylene group having from about 1 to 6 carbon atoms; R ⁶ in each of the groups x (R ⁶ O) and y (R ⁶ O) independently represents ethylene or propylene; R ⁷ represents hydrogen or a straight or branched alkyl group having from 1 to about 4 carbon atoms; x represents an average of from 1 to about 10, and y represents an average of from 0 to about 50.

(k) mono- or di-quaternary ammonium salts having the formula:

or

where R ¹ , R ³ , R ⁴ , R ⁵ , R ⁸ and R ⁹ independently represent hydrogen, polyhydroxyalkyl, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, or - (R ⁶ O) _x R ⁷ ; R ² is hydrocarbylene or substituted hydrocarbylene having from 2 to about 30 carbon atoms, R ⁶ in each of the groups x (R ⁶ O) and y (R ⁶ O) independently represent C ₂ -C ₄ alkylene; R ⁷ represents hydrogen or a straight or branched alkyl group having from 1 to about 4 carbon atoms; x is an average number from 1 to about 30, y is an average number from about 3 to about 60, and X ^- is an agriculturally acceptable anion. In this context, preferred hydrocarbyl (hydrocarbylene) groups R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁸ and R ⁹ are straight or branched alkyl (alkylene), straight or branched alkenyl (alkenylene), straight or branched alkynyl (alkynylene), aryl (arylene) or aralkyl (aralkylene) groups. Preferably, R ¹ , R ³ , R ⁴ , R ⁵ , R ⁸ and R ⁹ independently represent hydrogen or a straight or branched alkyl or alkenyl group having from about 1 to 22 carbon atoms or - (R ⁶ O) _x R ⁷ ; R ² represents a straight or branched alkylene or alkenylene group having from about 1 to 6 carbon atoms; R ⁶ in each of the groups x (R ⁶ O) and y (R ⁶ O) independently represents C ₂ -C ₄ alkylene; R ⁷ represents hydrogen or a straight or branched alkyl group having from 1 to about 4 carbon atoms; x represents an average of from 1 to about 30, and y represents an average of from 1 to about 60. More preferably, R ¹ , R ³ , R ⁴ , R ⁵ , R ⁸ and R ⁹ independently represent hydrogen or a straight or branched alkyl group, having about 1 to 18 carbon atoms or - (R ⁶ O) _x R ⁷ ; R ² represents a straight or branched alkylene group having from about 1 to 6 carbon atoms; R ⁶ in each of the groups x (R ⁶ O) and y (R ⁶ O) independently represents ethylene or propylene; R ⁷ represents hydrogen or a straight or branched alkyl group having from 1 to about 4 carbon atoms; x represents an average of from 1 to about 10, and y represents an average of from about 1 to 60. Most preferably, R ¹ and R ³ independently represent straight or branched alkyl groups having from about 8 to 18 carbon atoms, and R ⁴ , R ⁵ , R ⁸ and R ⁹ independently represent hydrogen or methyl; R ² represents a straight or branched alkylene group having from about 1 to 6 carbon atoms; R ⁶ in each of the groups x (R ⁶ O) and y (R ⁶ O) independently represents ethylene or propylene; R ⁷ represents hydrogen or a straight or branched alkyl group having from 1 to about 4 carbon atoms; x represents an average of from 1 to about 10, and y represents an average of from 10 to about 50.

(l) a secondary or tertiary amine having the formula:

where R ¹ and R ² represent hydrocarbyl having from 1 to about 30 carbon atoms, and R ³ represents hydrogen or hydrocarbyl having from 1 to about 30 carbon atoms. In this context, preferred hydrocarbyl groups R ¹ , R ² and R ³ are straight or branched alkyl, straight or branched alkenyl, straight or branched alkynyl, aryl or aralkyl groups. Preferably R ¹ represents a straight or branched alkyl or straight or branched alkenyl group having from about 8 to 30 carbon atoms, and R ² and R ³ independently represent hydrogen or a straight or branched alkyl group or a straight or branched alkenyl group having from 1 to about 6 carbon atoms. More preferably, R ¹ represents a straight or branched alkyl group having from about 12 to 22 carbon atoms, and R ² and R ³ independently represent hydrogen, methyl or ethyl. In one embodiment of the amine of formula (32), R ¹ represents a straight or branched alkyl group having from about 12 to 22 carbon atoms, and R ² and R ³ independently represent straight or branched hydroxyalkyl groups having from 1 to about 6 carbon atoms .

In one embodiment, the surfactant has the formula (23), wherein R ¹ is hydrocarbyl or substituted hydrocarbyl having from about 8 to 30 carbon atoms, R ² is a hydroxyalkyl, polyhydroxyalkyl, or poly (hydroxyalkyl) alkyl group, and R ³ represents hydrogen, hydroxyalkyl, polyhydroxyalkyl or poly (hydroxyalkyl) alkyl. In this context, preferred R ¹ hydrocarbyl groups are straight or branched alkyl, straight or branched alkenyl, straight or branched alkynyl, aryl or aralkyl groups. In one embodiment, R ¹ represents a straight or branched alkyl, straight or branched alkenyl, straight or branched alkynyl, aryl or aralkyl group having from about 8 to 30 carbon atoms, R ² represents a straight or branched hydroxyalkyl group having from 1 up to about 6 carbon atoms, and R ³ represents hydrogen or a straight or branched hydroxyalkyl group having from 1 to about 6 carbon atoms. Preferably R ¹ represents a straight or branched alkyl, straight or branched alkenyl, straight or branched alkynyl, aryl or aralkyl group having from about 8 to 22 carbon atoms, R ² represents a straight or branched hydroxyalkyl group having from 1 to about 4 carbon atoms and R ³ represents hydrogen or a straight or branched hydroxyalkyl group having from about 1 to 4 carbon atoms. More preferably, R ¹ represents a straight or branched alkyl, straight or branched alkenyl, straight or branched alkynyl, aryl or aralkyl group having from about 8 to 18 carbon atoms, R ² represents hydroxymethyl or hydroxyethyl, and R ³ represents hydrogen, hydroxymethyl or hydroxyethyl .

(m) monoalkoxylated amines having the formula:

where R ¹ and R ⁴ independently represent a hydrocarbyl or substituted hydrocarbyl group having from 1 to about 30 carbon atoms, or —R ⁵ SR ⁶ ; R ² in each of the groups x (R ² O) independently represents C ₂ -C ₄ alkylene; R ³ represents hydrogen or a straight or branched alkyl group having from 1 to about 4 carbon atoms; R ⁵ represents a straight or branched alkyl group having from about 6 to 30 carbon atoms; R ⁶ represents a hydrocarbyl or substituted hydrocarbyl group having from 4 to about 15 carbon atoms, and x represents an average of 1 to about 60. In this context, preferred hydrocarbyl groups of R ¹ , R ⁴ and R ⁶ are straight or branched alkyl, straight or branched alkenyl, straight or branched alkynyl, aryl or aralkyl groups. In one embodiment, R ¹ comprises from about 7 to 30 carbon atoms, preferably from about 8 to 22 carbon atoms, and the remaining groups are as described above. Preferably, R ¹ and R ⁴ independently represent a straight or branched alkyl or straight or branched alkenyl group having from about 1 to 25 carbon atoms, R ² in each of the groups x (R ² O) independently represents C ₂ -C ₄ alkylene, R ³ represents hydrogen, methyl or ethyl, and x represents an average of from 1 to about 40. More preferably, R ¹ and R ⁴ independently represent a straight or branched alkyl group having from 1 to about 22 carbon atoms, R ² in each of the groups x (R ² O) independently represents ethylene or propylene, R ³ p represents hydrogen or methyl, and x represents an average of from 1 to about 30. Even more preferably, R ¹ represents a straight or branched alkyl group having from about 8 to 22 carbon atoms, R ⁴ represents a straight or branched alkyl group having from 1 to about 22 carbon atoms; R ² in each of the groups x (R ² O) independently represents ethylene or propylene, R ³ represents hydrogen or methyl, and x represents an average of about 1 to 10. Most preferably, R ¹ represents a straight or branched alkyl group having from about 16 to 22 carbon atoms, and R ⁴ represents methyl; R ² in each of the groups x (R ² O) represents ethylene; R ³ represents hydrogen, and x represents an average of about 1 to 5, or R ¹ represents a straight or branched alkyl group having from about 8 to 15 carbon atoms, R ⁴ represents methyl; R ² in each of the groups x (R ² O) represents ethylene; R ³ represents hydrogen, and x represents an average of about 5 to 10.

(n) dialkoxylated quaternary ammonium salts of the formula:

where R ¹ represents hydrocarbyl or substituted hydrocarbyl having from about 1 to 30 carbon atoms; R ² in each of the groups x (R ² O) and y (R ² O) independently represents C ₂ -C ₄ alkylene; R ³ represents hydrogen or a straight or branched alkyl group having from 1 to about 4 carbon atoms; R ⁴ represents hydrogen or hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms; x and y independently represent an average of from 1 to about 40, and X ^- represents an agriculturally acceptable anion. In this context, preferred hydrocarbyl groups R ¹ and R ⁴ are straight or branched alkyl, straight or branched alkenyl, straight or branched alkynyl, aryl or aralkyl groups. Preferably, R ¹ and R ⁴ independently represent a straight or branched alkyl or straight or branched alkenyl group having from 1 to about 25 carbon atoms, R ² in each of the groups x (R ² O) and y (R ² O) independently represents C ₂ -C ₄ alkylene; R ³ is hydrogen, methyl or ethyl, and the sum of x and y is an average of about 2 to 30. More preferably, R ¹ and R ⁴ independently represent a straight or branched alkyl group having from 1 to about 22 carbon atoms, R ² in each of the groups x (R ² O) and y (R ² O) independently represents ethylene or propylene; R ³ is hydrogen or methyl, and the sum of x and y is an average of about 2 to 20. Even more preferably, R ¹ independently represents a straight or branched alkyl group having from about 8 to 22 carbon atoms, and R ⁴ represents a straight or branched an alkyl group having from 1 to about 22 carbon atoms; R ² in each of the groups x (R ² O) and y (R ² O) independently represents ethylene or propylene; R ³ represents hydrogen or methyl, and x represents an average of from about 2 to 20. Most preferably, R ¹ represents a straight or branched alkyl group having from about 8 to 22 carbon atoms, and R ⁴ represents a straight or branched alkyl group having from 1 to about 6 carbon atoms; R ² in each of the groups x (R ² O) and y (R ² O) independently represents ethylene or propylene; R ³ represents hydrogen or methyl, and x represents an average of about 2 to 15, or R ¹ and R ⁴ independently represent a straight or branched alkyl group having from about 8 to 22 carbon atoms; R ² in each of the groups x (R ² O) and y (R ² O) independently represents ethylene or propylene; R ³ is hydrogen or methyl, and x is an average of from 5 to about 15. Preferred dialkoxylated quaternary ammonium surfactants are Ethoquad ^TM C12 (PEG (2) -cocomethylammonium chloride from Akzo Nobel), PEG chloride (5) - cocomethylammonium, PEG (5) methyl chloride tall oil, PEG dibromide (5) tall oil ammonium, and PEG dibromide (10) tall oil ammonium.

(o) salts of monoalkoxylated quaternary ammonium having the formula:

where R ¹ and R ⁵ independently represent hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms; R ⁴ represents hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms; R ² in each of the groups x (R ² O) independently represents C ₂ -C ₄ alkylene; R ³ represents hydrogen or a straight or branched alkyl group having from 1 to about 30 carbon atoms; x represents the average number of from 1 to 60, and X ^- is an agriculturally acceptable anion. In this context, preferred hydrocarbyl groups R ¹ , R ⁴ and R ⁵ are straight or branched alkyl, straight or branched alkenyl, straight or branched alkynyl, aryl or aralkyl groups. Preferably, R ¹ , R ⁴ and R ⁵ independently represent a straight or branched alkyl or straight or branched alkenyl group having from 1 to about 25 carbon atoms, R ² in each of the groups x (R ² O) independently represents C ₂ -C ₄ alkylene; R ³ represents hydrogen, methyl or ethyl, and x represents an average of from 1 to about 40. More preferably, R ¹ , R ⁴ and R ⁵ independently represent a straight or branched alkyl group having from 1 to about 22 carbon atoms, R ² in each of the groups x (R ² O) independently represents ethylene or propylene; R ³ represents hydrogen or methyl, and x represents an average of from 1 to about 30. Even more preferably, R ¹ represents a straight or branched alkyl group having from about 8 to 22 carbon atoms, R ² in each of the groups x (R ² O ) independently represents ethylene or propylene; R ³ represents hydrogen or methyl, R ⁴ and R ⁵ independently represent a straight or branched alkyl group having from 1 to about 22 carbon atoms, and x represents an average of 1 to about 30. Even more preferably, R ¹ represents a straight or branched alkyl group having from about 8 to 22 carbon atoms, R ² in each of the x (R ² O) is independently ethylene or propylene; R ³ represents hydrogen or methyl, R ⁴ and R ⁵ independently represent a straight or branched alkyl group having from 1 to about 6 carbon atoms, and x represents an average of about 5 to 25. Most preferably, R ¹ represents a straight or branched alkyl group having about 16 to 22 carbon atoms, R ² in each of the x (R ² O) groups independently represents ethylene or propylene; R ³ represents hydrogen or methyl, R ⁴ and R ⁵ independently represent a straight or branched alkyl group having from 1 to about 3 carbon atoms, and x represents an average of from about 5 to 25. Preferred monoalkoxylated quaternary ammonium surfactants are PEG (7) -C ₁₈ dimethylammonium chloride and PEG (22) -C ₁₈ dimethylammonium chloride.

(p) Quaternary ammonium salts having the formula:

where R ¹ , R ³ and R ⁴ independently represent hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms; R ² represents hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms; and X ^- is an agriculturally acceptable anion. In this context, preferred hydrocarbyl groups R ¹ , R ² , R ³ and R ⁴ represent straight or branched alkyl, straight or branched alkenyl, straight or branched alkynyl, aryl or aralkyl groups. Preferably R ¹ represents a straight or branched alkyl or straight or branched alkenyl group having from about 8 to 30 carbon atoms, and R ² , R ³ and R ⁴ independently represent a straight or branched alkyl or straight or branched alkenyl group having from 1 to approximately 30 carbon atoms. More preferably, R ¹ represents a straight or branched alkyl or straight or branched alkenyl group having from about 8 to 22 carbon atoms, and R ² , R ³ and R ⁴ independently represent a straight or branched alkyl or straight or branched alkenyl group having from 1 up to about 6 carbon atoms. Even more preferably, R ¹ represents a straight or branched alkyl group having from about 8 to 16 carbon atoms, and R ² , R ³ and R ⁴ independently represent a straight or branched alkyl group having from 1 to about 6 carbon atoms. Most preferably, R ¹ represents a straight or branched alkyl group having from about 8 to 14 carbon atoms, and R ² , R ³ and R ⁴ independently represent methyl. Preferred commercially available quaternary ammonium surfactants are Arquad ^™ C-50 (dozocyltrimethylammonium chloride from Akzo Nobel) and Arquad ^™ T-50 (tall oil trimethylammonium chloride from Akzo Nobel).

(q) ethers having the formula:

where R ¹ represents hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms; R ² is hydrocarbylene or substituted hydrocarbylene having from 2 to about 30 carbon atoms; R ³ and R ⁴ independently represent hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, or - (R ⁵ O) _x R ⁶ , R ⁵ in each of the groups x (R ⁵ -O) independently represents C ₂ -C ₄ alkylene, R ⁶ represents hydrogen or a straight or branched alkyl group having from 1 to about 4 carbon atoms, and x represents an average of from 1 to about 50. In this context, preferred hydrocarbyl (hydrocarbylene) groups R ¹ , R ² , R ³ and R ⁴ are straight or branched alkyl (alkylene), straight or branched alkenyl (alkenylene), straight or branched alkynyl (alkynylene), aryl (arylene) or aralkyl (aralkylene) groups. Preferably, R ¹ is a straight or branched alkyl, straight or branched alkenyl, straight or branched alkynyl, aryl or aralkyl group having from 8 to about 25 carbon atoms, R ² is a straight or branched alkylene group or an alkenylene group having from 2 to about 2 30 carbon atoms, R ³ and R ⁴ independently represent hydrogen or a straight or branched alkyl, straight or branched alkenyl group, a straight or branched alkynyl, aryl or aralkyl group PPs having from 1 to about 30 carbon atoms or - (R ⁵ O) _x R ⁶ ; R ⁵ in each of the groups x (R ⁵ O) independently represents C ₂ -C ₄ alkylene, R ⁶ represents hydrogen, methyl or ethyl, and x represents an average of 1 to about 30. More preferably, R ¹ represents a straight or branched alkyl or an alkenyl group having from 8 to about 22 carbon atoms, R ² represents a straight or branched alkylene group or an alkenylene group having from 2 to about 6 carbon atoms, R ³ and R ⁴ independently represent hydrogen or a straight or branched alkyl or alkenyl group having from 1 to pr approximately 6 carbon atoms or - (R ⁵ O) _x R ^6; R ⁵ in each of the groups x (R ⁵ O) independently represents ethylene or propylene, R ⁶ represents hydrogen or methyl, and x represents an average of about 1 to 15. Most preferably, R ¹ represents a straight or branched alkyl or alkenyl group having from about 8 to 18 carbon atoms, R ² represents ethylene or propylene; R ³ and R ⁴ independently represent hydrogen, methyl or - (R ⁵ O) _x R ⁶ ; R ⁵ in each of the groups x (R ⁵ O) independently represents ethylene or propylene, R ⁶ represents hydrogen, and x represents an average of from 1 to about 5.

(r) diamines having the formula:

where R ¹ , R ³ , R ⁴ and R ⁵ independently represent hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, or - (R ⁶ O) _x R ⁷ ; R ² and R ⁸ independently represent hydrocarbylene or substituted hydrocarbylene having from 2 to about 30 carbon atoms; R ⁶ in each of the groups x (R ⁶ O) and y (R ⁶ O) independently represents C ₂ -C ₄ alkylene; R ⁷ represents hydrogen or a straight or branched alkyl group having from 1 to about 30 carbon atoms; x represents an average of from 1 to about 30, X represents —O—, —N (R ⁶ ) -, —C (O) -, —C (O) O—, —OC (O) -, —N (R ⁹ ) C (O) -, -C (O) N (R ⁹ ) -, -S-, -SO or -SO ₂ ; y represents 0 or an average of 1 to about 30, n and z independently represent 0 or 1, and R ⁹ represents hydrogen or hydrocarbyl or substituted hydrocarbyl. In this context, preferred hydrocarbyl (hydrocarbylene) groups R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ⁹ are straight or branched alkyl (alkylene), straight or branched alkenyl (alkenylene), straight or branched alkynyl (alkynylene) , aryl (arylene) or aralkyl (aralkylene) groups. Preferably, R ¹ and R ⁴ independently represent a straight or branched alkyl or straight or branched alkenyl group having from about 1 to 22 carbon atoms, R ² and R ⁸ independently represent straight or branched alkylene groups having from about 2 to 25 carbon atoms, each of R ³ and R ⁵ independently represents hydrogen or a straight or branched alkyl group having from 1 to about 6 carbon atoms, and n, y and z are 0; or R ¹ , R ² , R ³ and R ⁴ independently represent hydrogen or a straight or branched alkyl or alkenyl group having from about 1 to 6 carbon atoms, R ² represents a straight or branched alkylene or alkenylene group having from about 8 to 25 carbon atoms, and n, y and z are 0; or R ¹ , R ² , R ³ and R ⁴ independently represent hydrogen or a straight or branched alkyl or alkenyl group having from about 1 to 6 carbon atoms, R ² represents a straight or branched alkylene or alkenylene group having from about 1 to 6 carbon atoms; R ⁶ in each of the y groups (R ⁶ O) independently represents C ₂ -C ₄ alkylene; y represents an average of from 1 to about 20, and n and z are 0; or R ¹ and R ³ independently represent a straight or branched alkyl or alkenyl group having from about 8 to 22 carbon atoms, R ² represents a straight or branched alkylene group having from about 2 to 25 carbon atoms; and each of R ⁴ and R ⁵ independently represents hydrogen, a straight or branched alkyl or alkenyl group having from 1 to about 6 carbon atoms, or - (R ⁶ O) _x R ⁷ ; R ⁶ in each of the groups x (R ⁶ O) independently represents C ₂ -C ₄ alkylene; R ⁷ represents hydrogen or a straight or branched alkyl group having from 1 to about 4 carbon atoms; x is an average of 1 to about 30, and n, y and z are 0, or R ¹ is a straight or branched alkyl or straight or branched alkenyl group having from about 1 to 22 carbon atoms; R ² represents a straight or branched alkylene group having from about 2 to 25 carbon atoms, each of R ³ , R ⁴ and R ⁵ independently represents hydrogen or a straight or branched alkyl group having from about 1 to 6 carbon atoms, X represents - C (O) - or —SO ₂ , n and y are 0 and z is 1. More preferably, R ¹ and R ⁴ independently represent hydrogen or a straight or branched alkyl or straight or branched alkenyl group having from about 4 to 18 atoms carbon, R ² represents a straight or branched alkylene g a group having about 2 to 6 carbon atoms, each of R ³ and R ⁵ independently represents hydrogen or a straight or branched alkyl group having from 1 to about 6 carbon atoms, and n, y and z are 0; or R ¹ , R ² , R ³ and R ⁴ independently represent hydrogen or a straight or branched alkyl group having from about 1 to 6 carbon atoms, R ² represents a straight or branched alkylene group having from about 8 to 25 carbon atoms, and y is 0; or R ¹ , R ² , R ³ and R ⁴ independently represent hydrogen or a straight or branched alkyl group having from about 1 to 6 carbon atoms, R ² represents a straight or branched alkylene group having from about 1 to 6 carbon atoms; R ⁶ in each of the y groups (R ⁶ O) independently represents ethylene or propylene; y represents an average of 1 to about 10, and n and z are 0; or R ¹ and R ³ independently represent a straight or branched alkyl group having from about 8 to 22 carbon atoms, R ² represents a straight or branched alkylene group having from about 2 to 6 carbon atoms; and each of R ⁴ and R ⁵ independently represents hydrogen or a straight or branched alkyl group having from about 1 to 6 carbon atoms, or - (R ⁶ O) _x R ⁷ ; R ⁶ in each of the groups x (R ⁶ O) independently represents ethylene or propylene; R ⁷ represents hydrogen or methyl; x represents an average of from 1 to about 15, and n, y and z are 0, or R ¹ represents a straight or branched alkyl group having from about 1 to 22 carbon atoms; R ² represents a straight or branched alkylene group having from about 2 to 6 carbon atoms, each of R ³ , R ⁴ and R ⁵ independently represents hydrogen, X represents —C (O) - or —SO ₂ , n and y are 0 and z is 1. Preferred diamines are Gemini 14-2-14, Gemini 14-3-14, Gemini 10-2-10, Gemini 10-3-10, Gemini 10-4-10 and Gemini 16-2-16 (C ₁₀ -, C ₁₄ - or C ₁₆ ethylene, propylene or butylene N-methyldiamines from Monsanto), Ethoduomeens ^TM and Jeffamine ^TM EDR-148.

(s) amine oxides having the formula:

where R ¹ , R ² and R ³ independently represent hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, - (R ⁴ O) _x R ⁵ , or -R ⁶ (OR ⁴ ) _x OR ⁵ ; R ⁴ in each of the groups x (R ⁴ O) independently represents C ₂ -C ₄ alkylene; R ⁵ represents hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms; R ⁶ is hydrocarbylene or substituted hydrocarbylene having from 1 to about 6 carbon atoms; x represents an average of from 1 to about 50, and the total number of carbon atoms in R ¹ , R ² and R ³ is at least 8. In this context, preferred hydrocarbyl (hydrocarbylene) groups R ¹ , R ² , R ³ , R ⁵ and R ⁶ are straight or branched alkyl (alkylene), straight or branched alkenyl (alkenylene), straight or branched alkynyl (alkylene), aryl (arylene) or aralkyl (aralkylene) groups. Preferably, R ¹ and R ² independently represent hydrogen or a straight or branched alkyl or straight or branched alkenyl group having from 1 to about 30 carbon atoms, or - (R ⁴ O) _x R ⁵ ; R ³ represents a straight or branched alkyl or straight or branched alkenyl group having from about 8 to 30 carbon atoms; R ⁴ in each of the groups x (R ⁴ O) independently represents C ₂ -C ₄ alkylene; R ⁵ represents hydrogen or a straight or branched alkyl or straight or branched alkenyl group having from 1 to about 30 carbon atoms; and x represents an average of from 1 to about 30. More preferably, R ¹ and R ² independently represent hydrogen or a straight or branched alkyl group having from 1 to about 6 carbon atoms, and R ³ represents a straight or branched alkyl group having from about 8 to 22 carbon atoms, or R ¹ and R ² independently represent - (R ⁴ O) _x R ⁵ ; R ³ represents a straight or branched alkyl group having from about 8 to 22 carbon atoms; R ⁴ in each of the groups x (R ⁴ O) independently represents ethylene or propylene; R ⁵ represents hydrogen or a straight or branched alkyl or straight or branched alkenyl group having from 1 to about 30 carbon atoms; and x represents an average of from 1 to about 10. Most preferably, R ¹ and R ² independently represent methyl, and R ³ represents a straight or branched alkyl group having from about 8 to 18 carbon atoms, or R ¹ and R ² independently represent - (R ⁴ O) _x R ⁵ ; R ³ represents a straight or branched alkyl group having from about 8 to 18 carbon atoms; R ⁴ in each of the groups x (R ⁴ O) independently represents ethylene or propylene; R ⁵ represents hydrogen or an alkyl group having from about 8 to 18 carbon atoms; and x represents an average of 1 to about 5. Commercially available amine oxide surfactants are L70 chemoxide.

(t) alkoxylated amine oxides having the formula:

where R ¹ represents hydrogen or hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms; R ² in each of the groups x (R ² O) and y (R ² O) independently represents C ₂ -C ₄ alkylene; R ³ is hydrocarbylene or substituted hydrocarbylene having from 2 to about 6 carbon atoms; each of R ⁴ and R ⁵ independently represents hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms; - (R ⁶ ) _n - (R ² O) _y R ⁷ , R ⁶ represents hydrocarbylene or substituted hydrocarbylene having from about 1 to 6 carbon atoms, R ⁷ represents hydrogen or a straight or branched alkyl group having from 1 to about 4 carbon atoms; n represents 0 or 1, and x and y independently represent an average of 1 to about 60. In this context, preferred hydrocarbyl (hydrocarbylene) groups R ¹ , R ⁴ , R ⁵ and R ⁶ are straight or branched alkyl (alkylene), straight or branched alkenyl (alkenylene), straight or branched alkynyl (alkynylene), aryl (arylene) or aralkyl (aralkylene) groups. Preferably R ¹ represents a straight or branched alkyl or straight or branched alkenyl group having from about 8 to 25 carbon atoms, R ² in each of the x (R ² O) groups independently represents C ₂ -C ₄ alkylene, R ³ represent straight or a branched alkylene or alkenylene group having from 2 to about 6 carbon atoms, each of R ⁴ and R ⁵ independently represents hydrogen or a straight or branched alkyl group having from 1 to about 6 carbon atoms, and x represents an average of from 1 to about 30. More than preferably R ¹ represents a straight or branched alkyl group having from about 12 to 22 carbon atoms, R ² in each of the x (R ² O) groups independently represents ethylene or propylene, R ³ represents a straight or branched alkylene or alkenylene group having 2 to about 6 carbon atoms, each of R ⁴ and R ⁵ independently represents hydrogen, methyl or tris (hydroxymethyl) methyl, and x represents an average of about 2 to 30. Even more preferably, R ¹ represents a straight or branched alkyl group having example but from 12 to 18 carbon atoms, R ² in each of the groups x (R ² O) independently represents ethylene or propylene, R ³ represents an ethylene, propylene or 2-hydroxypropylene group, each of R ⁴ and R ⁵ independently represents hydrogen or methyl and x represents an average of about 4 to 20. Most preferably, R ¹ represents a straight or branched alkyl group having from about 12 to 18 carbon atoms, R ² in each of the x (R ² O) groups independently represents ethylene or propylene, R ³ represents ethylene, propylene or 2-hydroxypropi a len group, R ⁴ and R ⁵ represents methyl, and x represents an average of about 4 to 20.

(u) dialkoxylated amines having the formula:

where R ¹ represents hydrogen or hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, —R ⁴ SR ⁵ , or - (R ² O) _z R ³ , R ² in each of the groups x (R ² O), y (R ² O) and z (R ² O) independently represents C ₂ -C ₄ alkylene; R ³ represents hydrogen or a straight or branched alkyl group having from 1 to about 22 carbon atoms, R ⁴ represents a straight or branched alkyl group having from about 6 to 30 carbon atoms; R ⁵ represents a straight or branched alkyl group having from about 4 to 15 carbon atoms; and x, y and z independently represent an average of from 1 to about 40. In this context, preferred R ¹ hydrocarbyl groups are hydrogen, straight or branched alkyl, straight or branched alkenyl, straight or branched alkynyl, aryl or aralkyl groups. Preferably R ¹ represents hydrogen, a straight or branched alkynyl, aryl or aralkyl group having from about 1 to 30 carbon atoms, R ² in each of the groups x (R ² O), y (R ² O) and z (R ² O ) independently represents C ₂ -C ₄ alkylene; R ³ represents hydrogen, methyl or ethyl, and x, y and z independently represent an average of from 1 to about 20. More preferably, R ¹ represents hydrogen, a straight or branched alkynyl, aryl or aralkyl group having from about 8 to 25 carbon atoms , R ² in each of the groups x (R ² O), y (R ² O) and z (R ² O) independently represents ethylene or propylene; R ³ represents hydrogen or methyl, and x and y independently represent an average of from 1 to about 30. Even more preferably, R ¹ represent hydrogen, a straight or branched alkynyl, aryl or aralkyl group having from about 8 to 22 carbon atoms, R ² in each of the groups x (R ² O), y (R ² O) and z (R ² O) independently represents ethylene or propylene; R ³ represents hydrogen or methyl, and x and y independently represent an average of 1 to about 5. Preferred commercially available dialkoxylated amines are Trymeen ^™ 6617 (from Cognis) and Ethomeen ^™ C / 12, C / 15, C / 20, C / 25, T / 12, T / 15, T / 20 and T / 25 (from Akzo Nobel).

(v) aminated alkoxylated alcohols having the following chemical structure:

where each of R ¹ , R ⁷ , R ⁸ and R ⁹ independently represents hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, or - (R ¹¹ ) _s (R ³ O) _v R ¹⁰ ; X represents —O—, —OC (O) -, —C (O) O—, —N (R ¹² ) C (O) -, —C (O) N (R ¹² ) -, —S—, - SO, —SO ₂ or —N (R ⁹ ) -; R ³ in each of the groups n (R ³ O) and v (R ³ O) independently represents C ₂ -C ₄ alkylene; R ¹⁰ represents hydrogen or a straight or branched alkyl group having from about 1 to 30 carbon atoms, n represents an average of from 1 to about 60, v represents an average of from 1 to about 50; each of R ² and R ¹¹ independently represents hydrocarbylene or substituted hydrocarbylene having from 1 to about 6 carbon atoms; R ⁴ is hydrocarbylene or substituted hydrocarbylene having from 2 to about 6 carbon atoms; R ¹² represents hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms; each of m and s independently is 0 or 1; R ⁶ is hydrocarbylene or substituted hydrocarbylene having from 2 to about 30 carbon atoms, —C (═NR ¹² ) -, C (S) or —C (O) -; q represents an integer from 0 to 5; and R ⁵ represents hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms. In this context, preferred hydrocarbyl (hydrocarbylene) groups R ¹ , R ² , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹¹ and R ¹² are straight or branched alkyl (alkylene), straight or branched alkenyl (alkenylene), straight or branched alkynyl (alkynylene), aryl (arylene) or aralkyl (aralkylene) groups; and

(w) fatty imidazolines used herein represented by the formula:

where R ¹ and R ² independently represent H or a substituted or unsubstituted C ₁ -C ₂₂ fatty acid.

In one embodiment, any of the amine or quaternary ammonium surfactants described in (a) to (v) above is included in non-IPA glyphosate liquid glyphosate concentrates, such as for example glyphosate concentrates, containing potassium, diammonium, ammonium, sodium, monoethanolamine, n-propylamine, methylamine, ethylamine, hexamethylenediamine, dimethylamine or trimethylsulfonium glyphosate salt, or mixtures thereof, which contain at least about 10 ma .% Ae glyphosate, more preferably at least about 15%, 20%, 25%, 30%, 35%, 40% or more wt.% ke glyphosate, or at least about 120 grams ke glyphosate per liter, more preferably at least 130, 140, 150, 160, 170, 180, 190, 200, 210, 220, 230, 240, 250, 260, 270, 280, 290, 300, 310, 320, 330, 340, 350, 360, 370, 380, 390 or 400 g ke / l or more.

In another embodiment, any of the cationic surfactants described above in (a) to (v) is preferably included in the concentrates not containing alkyl polyglycosides, or containing only alkyl polyglycosides having a low color intensity of less than 10, preferably less than 9, 8, 7, 6, or 5, measured with a Gardner colorimeter. When dye is added to the resulting glyphosate product having a Gardner color intensity of greater than about 10, the concentrate acquires a dark brown color. Concentrates having a Gardner color intensity of 10 are difficult to stain blue or green, which in most cases are necessary to distinguish a glyphosate product from other herbicidal products.

A subclass of such cationic surfactants described above includes a monoalkoxylated amine having the formula:

where R ¹ represents hydrogen or hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms; R ² in each of the groups x (R ² O) and y (R ² O) independently represents C ₂ -C ₄ alkylene; R ³ is hydrocarbylene or substituted hydrocarbylene having from 2 to about 30 carbon atoms; each of R ⁴ and R ⁵ independently represents hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms; - (R ⁶ ) _n - (R ² O) _y R ⁷ ; or R ⁴ and R ⁵ taken together with the nitrogen atom to which they are attached form a cyclic or heterocyclic ring; R ⁶ represents hydrocarbylene or substituted hydrocarbylene having from 1 to about 30 carbon atoms, R ⁷ represents hydrogen or a straight or branched alkyl group having from about 1 to 4 carbon atoms; n represents 0 or 1, and x and y independently represent an average of 1 to about 60. In this context, preferred hydrocarbyl (hydrocarbylene) groups R ¹ , R ³ , R ⁴ , R ⁵ and R ⁶ represent straight or branched alkyl (alkylene) ), straight or branched alkenyl (alkenylene), straight or branched alkynyl (alkynylene), aryl (arylene) or aralkyl (aralkylene) groups. Preferably R ¹ represents a straight or branched alkyl or straight or branched alkenyl group having from about 8 to 25 carbon atoms, R ² in each of the x (R ² O) groups independently represents C ₂ -C ₄ alkylene, R ³ represent straight or a branched alkylene group having from 2 to about 20 carbon atoms, each of R ⁴ and R ⁵ independently represents hydrogen or a straight or branched alkyl group having from about 1 to 6 carbon atoms, and x represents an average of from 1 to about 30. More preferably R ¹ pr represents a straight or branched alkyl group having from about 12 to 22 carbon atoms, R ² in each of the x (R ² O) groups independently represents ethylene or propylene, R ³ represents a straight or branched alkylene group having from 2 to about 6 atoms carbon, each of R ⁴ and R ⁵ independently represents hydrogen, methyl or tris (hydroxymethyl) methyl, and x represents an average of about 2 to 30. Even more preferably, R ¹ represents a straight or branched alkyl group having from about 12 to 18 carbon atoms, R ² each which of the groups x (R ² O) independently represents ethylene or propylene, R ³ represents ethylene or propylene, each of R ⁴ and R ⁵ independently represents hydrogen, methyl or tris (hydroxymethyl) methyl, and x represents an average of about 4 to 20. Most preferably, R ¹ represents a straight or branched alkyl group having from about 12 to 18 carbon atoms, R ² in each of the x (R ² O) groups independently represents ethylene or propylene, R ³ represents ethylene, R ⁴ and R ⁵ represent methyl, and x represents an average of about 4 to 20. Prefer monoalkoxylated amines are PEG (13) - or PEG (18) -C _14-15 ether-propylamines and PEG (7,10,15 or 20) -C _16-18 ether-propylamines (from Tomah) or PEG (13) - and PEG ( 18) C _14-15 efirodimetilpropilaminy and PEG (10, 13, 15, 20, or 25) -C efirodimetilpropilaminy _14-18 (from Tomah) and Surfonic AGM-550 ^TM from Huntsman.

Quaternary ammonium, sulfonium and sulfoxonium salts are also effective cationic surfactants for the preparation of glyphosate potassium salt concentrates and have a chemical structure:

or

or

or

where R ¹ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ and R ¹¹ independently represent hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, or - (R ¹³ ) _s (R ³ O) _v R ¹² ; X represents —O—, —OC (O) -, —N (R ¹⁴ ) C (O) -, —C (O) N (R ¹⁴ ) -, —C (O) O— or —S—; R ³ in each of the groups n (R ³ O) and v (R ³ O) independently represents C ₂ -C ₄ alkylene; R ¹² represents hydrogen or a straight or branched alkyl group having from 1 to about 30 carbon atoms, n represents an average of 1 to about 60, v represents an average of 1 to about 50, each of R ² and R ¹³ independently represents hydrocarbylene or substituted hydrocarbylene having from 1 to about 6 carbon atoms; each of m and s independently represents 0 or 1; R ⁴ is hydrocarbylene or substituted hydrocarbylene having from 2 to about 6 carbon atoms; R ⁶ is hydrocarbylene or substituted hydrocarbylene having from 2 to about 30 carbon atoms, —C (═NR ¹² ) -, —C (S) - or —C (O) -; R ¹⁴ represents hydrogen or hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms; q represents an integer from 0 to 5, R ⁵ represents hydrogen, hydrocarbyl or substituted hydrocarbyl having from about 1 to 30 carbon atoms; and each A ^- is an agriculturally acceptable anion. In this context, preferred hydrocarbyl (hydrocarbylene) groups R ¹ , R ² , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ , R ¹⁰ , R ¹¹ , R ¹³ and R ¹⁴ are straight or branched alkyl ( alkylene), straight or branched alkenyl (alkenylene), straight or branched alkynyl (alkylene), aryl (arylene) or aralkyl (aralkylene) groups.

Other cationic surfactants effective for preparing the compositions of the present invention are diamine or diammonium salts having the formulas:

or

where R ¹ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ independently represent hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms; R ² in each of the groups m (R ² O) and n (R ² O) and R ⁹ independently represent C ₂ -C ₄ alkylene; R ³ is hydrocarbylene or substituted hydrocarbylene having from about 2 to 6 carbon atoms, or - (R ² O) _p R ⁹ ; m and n separately represent an average of from 0 to about 50, and p represents an average of from 0 to about 60. In this context, preferred hydrocarbyl (hydrocarbylene) groups R ¹ , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ and R ⁸ are straight or branched alkyl (alkylene), straight or branched alkenyl (alkenylene), straight or branched alkynyl (alkylene), aryl (arylene) or aralkyl (aralkylene) groups. In one embodiment of formula (40), R ³ is hydrocarbylene having from about 2 to 6 carbon atoms, and the remaining groups are as defined above.

Some preferred cationic surfactants are alkylamine ethoxylates (including ester amines and diamines), such as tallow amine ethoxylate, cocoamine ethoxylate, etheroamine ethoxylate, tall oil N-ethylenediamine ethoxylate and amidoamine ethoxylates; alkylamine-containing quaternary amines, such as alkoxylated quaternary amines (for example, ethoxylated quaternary amines or propoxylated quaternary amines); alkylamine acetates, such as talloamine acetate or octylamine acetate; and amine oxides such as ethoxylated amine oxides (e.g. N-oxide N, N-bis (2-hydroxyethyl) cocoamine), unethoxylated amine oxides (e.g. cetyldimethylamine N-oxide) and amidoamine oxides.

Preferred nonionic surfactants suitable for preparing the herbicidal compositions and concentrates of the present invention are:

(a) alkoxylated alcohols having the formula:

where R ¹ represents hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms; R ² in each of the groups x (R ² O) independently represents C ₂ -C ₄ alkylene; R ³ represents hydrogen or a straight or branched alkyl group having from 1 to about 4 carbon atoms; and x represents an average of about 1 to 60. In this context, preferred R ¹ hydrocarbyl groups are straight or branched alkyl, straight or branched alkenyl, straight or branched alkynyl, aryl or aralkyl groups. Preferably R ¹ represents a straight or branched alkyl or straight or branched alkenyl group having from about 8 to 30 carbon atoms, R ² in each of the groups x (R ² O) independently represents C ₂ -C ₄ alkylene, R ³ represents hydrogen, methyl or ethyl, and x represents an average of about 5 to 50. More preferably, R ¹ represents a straight or branched alkyl group having from about 8 to 25 carbon atoms, R ² in each of the groups x (R ² O) independently represents ethylene or propylene, R ³ represent hydrogen or methyl, and x represents an average of about 8 to 40. Even more preferably, R ¹ represents a straight or branched alkyl group having from about 12 to 22 carbon atoms, R ² in each of the groups x (R ² O) independently represents ethylene or propylene, R ³ is hydrogen or methyl, and x is an average of about 8 to 30. Preferred commercially available alkoxylated alcohols are Procol ^TM LA-15 (from Protameen), Brij ^TM 35, Brij ^TM 76, Brij ^TM 78, Brij ^TM 97, and Brij ^TM 98 (from ^{Sigma Chemical Co.), Neodol TM 25-12} ( from Shell), Hetoxol ^TM CA-10, Hetoxol ^TM CA-20, Hetoxol ^TM CS-9, Hetoxol ^TM CS-15, Hetoxol ^TM CS- 20, Hetoxol ^TM CS-25, Hetoxol ^TM CS-30 and Plurafac ^TM A38 (from BASF), ST-8303 (from Cognis) and Arosurf ^TM 66 E20 (from Goldschmidt).

(b) dialkoxylated alcohols having the formula:

where R ¹ independently represents hydrogen or a straight or branched alkyl group having from 1 to about 4 carbon atoms; R ² in each of the groups x (R ² O) and y (R ² O) independently represents C ₂ -C ₄ alkylene; R ³ is hydrocarbylene or substituted hydrocarbylene having from 2 to about 30 carbon atoms; and x and y independently represent an average of from 1 to about 60. In this context, preferred R ³ hydrocarbyl groups are straight or branched alkylene, straight or branched alkenylene, straight or branched alkynylene, arylene or aralkylene groups. Preferably R ¹ represents hydrogen, methyl or ethyl, R ² in each of the groups x (R ² O) and y (R ² O) independently represents C ₂ -C ₄ alkylene; R ³ represents a straight or branched alkylene or straight or branched alkenylene group having from about 8 to 25 carbon atoms, and x and y independently represent an average of from about 1 to 20. More preferably, R ¹ is hydrogen or methyl, R ² in each from the groups x (R ² O) and y (R ² O) independently represents ethylene or propylene; R ³ represents a straight or branched alkylene or straight or branched alkenylene group having from about 8 to 18 carbon atoms, and x and y independently represent an average of from 1 to about 10. Even more preferably, R ¹ is hydrogen, R ² in each of groups x (R ² O) and y (R ² O) independently represent ethylene or propylene; R ³ represents a straight or branched alkylene group having from about 8 to 18 carbon atoms, and x and y independently represent an average of from 1 to about 5.

(c) alkoxylated dialkylphenols having the formula:

where R ¹ and R ⁴ independently represent hydrogen or a straight or branched alkyl group having from 1 to about 30 carbon atoms; and at least one of R ¹ and R ⁴ represents an alkyl group; R ² in each of the groups x (R ² O) independently represents C ₂ -C ₄ alkylene; R ³ represents hydrogen or a straight or branched alkyl group having from about 1 to 4 carbon atoms; and x represents an average of about 1 to 60. Preferably, R ¹ and R ⁴ independently represent straight or branched alkyl groups having from about 8 to 30 carbon atoms; R ² in each of the groups x (R ² O) independently represents C ₂ -C ₄ alkylene; R ³ represents hydrogen, methyl or ethyl; and x represents an average of about 5 to 50. More preferably, R ¹ and R ⁴ independently represent straight or branched alkyl groups having from about 8 to 22 carbon atoms; R ² in each of the groups x (R ² O) independently represents ethylene or propylene; R ³ represents hydrogen or methyl; and x represents an average of about 8 to 40. Even more preferably, R ¹ and R ⁴ independently represent straight or branched alkyl groups having from about 8 to 16 carbon atoms; R ² in each of the groups x (R ² O) independently represents ethylene or propylene; R ³ represents hydrogen or methyl; and x represents an average of about 10 to 30. Preferred commercially available alkoxylated dialkylphenols are ethoxylated dinonylphenols such as Surfonic ^™ DNP 100, Surfonic ^™ DNP 140 and Surfonic ^™ DNP 240 (from Huntsman).

(d) alkoxylated alkyl phenols having the formula:

where R ¹ represents a substituted or unsubstituted C ₁ -C ₂₂ group, and n is from 1 to about 20.

(e) alkoxylated mercaptans having the formula:

where R ¹ represents a substituted or unsubstituted C ₁ -C ₂₂ group, R ² represents methoxy, ethoxy or propoxy, and n is from 1 to about 20.

(f) alkylpyrrolidones having the formula:

where R ¹ represents a substituted or unsubstituted C ₁ -C ₂₂ group.

(g) alkoxylated alkanolamides having the formula:

where R ¹ represents a substituted or unsubstituted C ₁ -C ₂₂ group, R ² represents methoxy, ethoxy or propoxy, and n is from about 1 to 20; and

(h) alkoxylated glycols having the formula:

where R ¹ represents H, —OH or a substituted or unsubstituted C ₁ -C ₂₂ group, R ² represents methoxy, ethoxy or propoxy, R ³ represents H, —OH or a substituted or unsubstituted C ₁ -C ₂₂ group, and n equal to about 1 to 20.

Other suitable nonionic surfactants are alkyl polyglucosides; glycerol esters such as glyceryl monolaurate and ethoxylated glyceryl monococoate; ethoxylated castor oil; ethoxylated reduced sugar esters such as polyoxyethylene sorbitan monolaurate; esters of other polyols, such as sorbitan monolaurate and sucrose monostearate; ethoxylated amides, such as polyoxyethylene cocoamide; ethoxylated esters such as polyethylene glycol monolaurate 1000 and polyethylene glycol dilaurate 6000; ethoxylated alkyl or aryl phenols, such as nonyl phenol ethoxylate, octyl phenol ethoxylates, dodecyl phenol ethoxylates, dinonyl phenol ethoxylates and tristyl phenol ethoxylates; alcohol ethoxylates, such as fatty alcohol ethoxylates (for example, oleyl alcohol ethoxylate), tridecyl alcohol ethoxylates, and other alcohol ethoxylates, such as neodoles and oxo alcohol ethoxylates; and ethylene oxide / propylene oxide copolymers, such as pluronic, tetronic or tergitol XN copolymers.

Additional non-ionic surfactants for inclusion in the composition of surface-active substances that can be used in the present invention are polymerized with polyoxyethylene (5-30) C ₈ -C ₂₂ -alkyl esters and polymerized with polyoxyethylene (5-30) C ₈ - C ₁₂ -alkylphenyl esters, where “5-30” means that the average number of ethylene oxide units in the polyoxyethylene chains of these surfactants is from about 5 to 30. Examples of such nonionic surfactants are polyoxyethylenenonylphenols, octanols, decanols and trimethylnananols are available. Specific non-ionic surfactants approved for use are NEODOL ^TM 91-6 from Shell (polyoxyethylene (6) -C _9-11 primary straight chain alcohol), NEODOL ^TM 1-7 from Shell (polyoxyethylene (7) C _11- alcohol with primary direct chain), TERGITOL ^ТМ 15-S-9 from Union Carbide (polyoxyethylene (9) С _12-15- secondary alcohol) and SURFONIC ^ТМ NP95 from Huntsman (polyoxyethylene (9,5) -nonylphenol). Suitable polyalkoxylated silicone surfactants are those described in US Pat. No. 6,051,533, which is incorporated herein by reference.

In a preferred embodiment of the invention, said herbicidal compositions include at least one nonionic surfactant and at least one cationic surfactant. Any of the cationogenic and nonionic surfactants described herein can be used in combination in the herbicidal compositions of the present invention. Preferred cationic surfactants are alkylamine, alkyldiamine, alkylpolyamine, mono- or di-quaternary ammonium salt, monoalkoxylated amine, dialkoxylated amine such as ethoxylated tallowamines, monoalkoxylated quaternary ammonium salt, dialkoxylated quaternary ammonium oxide, ammonium oxide quaternary amine and imidazoline fatty series. Preferred nonionic surfactants are alkoxylated alcohol, dialkoxylated alcohol, alkoxylated dialkylphenol, alkylpolyglycoside, alkoxylated alkylphenol, alkoxylated glycol, alkoxylated mercaptan, alkoxylated, alkylene fatty acid, glyceryl, polyoxyalkyl fatty acid, glyceryl fatty acid, alkylene fatty acid, and N-alkylpyrrolidone. Examples of these surfactants are polyoxyethylene (5-30) C ₈ -C ₂₂ amines or polyoxyethylene (5-30) polyoxypropylene (2-10) C ₈ -C ₂₂ amines in combination with alkyl polyglucosides, alkoxylated or dialkoxylated alcohols such as polyoxyethylene (5-30) C ₈ -C ₂₂ alkyl esters or esters of methoxy, ethoxy or propoxy substituted glycols with a degree of substitution of from 1 to about 20. Cationic and nonionic surfactants suitable for use in the compositions of the present invention, is Compounds are described in US Pat. No. 6,245,713, which is incorporated herein by reference. If the surfactant component of the compositions of the present invention includes both cationic and nonionic surfactants, the mass ratio of nonionic surfactant to cationic surfactant is from about 1:10 to 10: 1, preferably from about 1: 5 to 5: 1, and more preferably from about 1: 3 to 3: 1.

The herbicidal compositions of the present invention may also include a compound capable of reducing eye irritation. Such compounds are usually effective in combination with alkylamine surfactants described herein and have the formula:

where R ₁ represents a hydrocarbyl group having from about 8 to 22 carbon atoms, each of the n (R ₂ O) groups independently represents C ₂ -C ₄ alkylene, n is a number from about 0 to 60, and X ₁ represents a carboxylate, sulfate or phosphate. These compounds are described in US Pat. No. 6,063,733, which is incorporated herein by reference.

Suitable amphoteric surfactants are betaines such as simple betaines (e.g. cocodimethyl betaine), sulfobetaines, amidobetaines and cocoamidosulfobetaines; imidazolinium compounds such as disodium lauroamphodiacetate, cocoamphoacetate sodium, cocoamphopropionate sodium, disodium cocoamino dipropionate, and cocoamphohydroxypropyl sulfonate; and other amphoteric surfactants such as N-alkyl, N-bis (2-hydroxyethyl) glycine and alkylamine dipropionates.

Other surfactants that can be used in the herbicidal compositions and concentrates of the present invention are compounds of the formulas:

or

or

or

or

or

or

or

or

where R ¹ , R ⁹ and R ¹² independently represent hydrocarbyl or substituted hydrocarbyl having from about 1 to 30 carbon atoms, or - (R ² O) _p R ¹³ ; R ² in each of the groups m (R ² O), n (R ² O), p (R ² O) and q (R ² O) independently represents C ₂ -C ₄ alkylene; R ³ , R ⁸ , R ¹¹ , R ¹³ and R ¹⁵ independently represent hydrogen, hydrocarbyl or substituted hydrocarbyl having from about 1 to 30 carbon atoms; R ⁴ represents - (CH ₂ ) _y OR ¹³ or - (CH ₂ ) _y O (R ² O) _q R ³ ; R ⁵ , R ⁶ and R ⁷ independently represent hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, or R ⁴ ; R ¹⁰ represents hydrocarbylene or substituted hydrocarbylene having from 2 to about 30 carbon atoms; R ¹⁴ represents hydrogen, hydrocarbyl or substituted hydrocarbyl having from 1 to about 30 carbon atoms, or - (CH ₂ ) _z O (R ² O) _p R ³ ; m, n, p and q independently represent an average of from 1 to about 50; X independently represents —O—, —NR ¹⁴ , —C (O) -, —C (O) O—, —OC (O) -, —N (R ¹⁵ ) C (O) -, —C (O) N (R ¹⁵ ) -, -S-, -SO, -SO ₂ ; t is 0 or 1; A ^- is an agriculturally acceptable anion; and y and z independently represent an integer from 0 to about 30. In this context, preferred hydrocarbyl (hydrocarbylene) groups R ¹ , R ³ and R ⁵ -R ¹⁵ are straight or branched alkyl (alkylene), straight or branched alkenyl (alkenylene) straight or branched alkynyl (alkynylene), aryl (arylene) or aralkyl (aralkylene) groups. Preferably, R ¹ , R ⁹ and R ¹² independently represent a straight or branched alkyl or alkenyl group having from 1 to about 22 carbon atoms or - (R ² O) _p R ¹³ , R ² in each of the m (R ² O) groups , n (R ² O), p (R ² O) and q (R ² O) independently represents C ₂ -C ₄ alkylene; R ³ represents hydrogen, methyl or ethyl, R ⁴ represents - (CH ₂ ) _y OR ¹³ or - (CH ₂ ) _y O (R ² O) _q R ³ ; R ⁵ , R ⁶ and R ⁷ independently represent hydrogen, a straight or branched alkyl or alkenyl group having from 1 to about 22 carbon atoms, or R ⁴ , R ⁸ , R ¹¹ , R ¹³ and R ¹⁵ independently represent hydrogen, direct or a branched alkyl or alkenyl group having from 1 to about 22 carbon atoms, R ¹⁰ represents a straight or branched alkylene or alkenylene group having from 2 to about 18 carbon atoms; R ¹⁴ represents a straight or branched alkyl or alkenyl group having from 1 to about 22 carbon atoms or - (CH ₂ ) _z O (R ² O) _p R ³ ; m, n, p and q independently represent an average of from 1 to about 30, X independently represents —O—, —N (R ¹⁴ ) -, —C (O) -, —C (O) O—, —OC ( O) -, -N (R ¹⁵ ) C (O) -, -C (O) N (R ¹⁵ ) -, -S-, -SO- or -SO ₂ ; t is 0 or 1, A ^- represents an agriculturally acceptable anion, and y and z independently represent an integer from 0 to about 30. More preferably, R ¹ represents a straight or branched alkyl or alkenyl group having from about 8 to 18 carbon atoms, or - (R ² O) _p R ¹³ , R ⁹ and R ¹² independently represent a straight or branched alkyl or alkenyl group having from 1 to about 22 carbon atoms or - (R ² O) _p R ¹³ ; R ² in each of the groups m (R ² O), n (R ² O), p (R ² O) and q (R ² O) independently represents ethylene or propylene; R ³ represents hydrogen or methyl; R ⁴ represents - (CH ₂ ) _y OR ¹³ or - (CH ₂ ) _y O (R ² O) _q R ³ ; R ⁸ , R ¹¹ and R ¹⁵ independently represent hydrogen, a straight or branched alkyl or alkenyl group having from 1 to about 22 carbon atoms, R ⁵ , R ⁶ and R ⁷ independently represent hydrogen or a straight or branched alkyl or alkenyl group having from 1 to about 22 carbon atoms, or R ⁴ ; R ¹⁰ represents a straight or branched alkylene or alkenylene group having from 2 to about 6 carbon atoms; R ¹³ represents hydrogen or a straight or branched alkyl or alkenyl group having from about 6 to 22 carbon atoms; R ¹⁴ represents a straight or branched alkyl or alkenyl group having from 1 to about 22 carbon atoms or - (CH ₂ ) _z O (R ² O) _p R ³ ; m, n, p and q independently represent an average of from 1 to about 20, X independently represents —O—, —N (R ¹⁴ ) -, —C (O) -, —C (O) O—, —OC ( O) -, -N (R ¹⁵ ) C (O) -, -C (O) N (R ¹⁵ ) -, -S-, -SO- or -SO ₂ ; t is 0 or 1, A ^- represents an agriculturally acceptable anion, and y and z independently represent an integer from 0 to 10. Most preferably, R ¹ represents a straight or branched alkyl or alkenyl group having from about 12 to 18 carbon atoms, or - (R ² O) _p R ¹³ , R ⁹ and R ¹² independently represent straight or branched alkyl or alkenyl groups having from 1 to about 6 carbon atoms or - (R ² O) _p R ¹³ ; R ² in each of the groups m (R ² O), n (R ² O), p (R ² O) and q (R ² O) independently represents ethylene or propylene; R ³ represents hydrogen; R ⁴ represents - (CH ₂ ) _y OR ¹³ or - (CH ₂ ) _y O (R ² O) _q R ³ ; R ⁸ , R ¹¹ and R ¹⁵ independently represent hydrogen, a straight or branched alkyl or alkenyl group having 1 to about 6 carbon atoms, R ⁵ , R ⁶ and R ⁷ independently represent hydrogen or a straight or branched alkyl or alkenyl group having from 1 to about 22 carbon atoms, or R ⁴ ; R ¹⁰ represents a straight or branched alkylene or alkenylene group having from 2 to about 6 carbon atoms; R ¹³ represents hydrogen or a straight or branched alkyl or alkenyl group having from about 6 to 22 carbon atoms; R ¹⁴ represents a straight or branched alkyl or alkenyl group having from 1 to about 22 carbon atoms or - (CH ₂ ) _z O (R ² O) _p R ³ ; m, n, p and q independently represent an average of from 1 to about 5; x independently represents —O— or —N (R ¹⁴ ) -; t is 0 or 1, A ^- represents an agriculturally acceptable anion, and y and z independently represent an integer from 1 to about 3.

Preferred anionic surfactants effective for preparing the compositions of the present invention are saturated carboxylic acids, such as butyric, nylon, caprylic, capric, lauric, palmitic, myristic or stearic acid, and unsaturated carboxylic acids, such as palmitoleic, oleic, linole or linolenic acid. Preferred carboxylic acids are palmitic, oleic or stearic acid. Other preferred anionic surfactants are alkyl sulfates, for example sodium lauryl sulfate and esters or diesters of phosphoric acid having the formula:

where R ¹ and R ³ independently represent a straight or branched alkyl, straight or branched alkenyl, straight or branched alkynyl, aryl or aralkyl groups having from about 4 to 30 carbon atoms; R ² in each of the groups m (R ² O) and n (R ² O) independently represents C ₂ -C ₄ alkylene; and m and n independently represent a number from 1 to about 30; or

where R ¹ represents a straight or branched alkyl, straight or branched alkenyl, straight or branched alkynyl, aryl or aralkyl groups having from about 8 to 30 carbon atoms; R ² in each of the groups m (R ² O) independently represents C ₂ -C ₄ alkylene; and m is from about 1 to 30. Representative phosphoric acid esters are olef-10-phosphate, olef-20-phosphate and olef-25-phosphate.

Preferred phosphate ester surfactants are phosphates of mono - and alcohol, mono - and di (polyoxyalkylene) alcohols and phosphates of mono - and alcohol, (poly-hydroxyalkylene alkylphenol) phosphates, which are represented by the formula:

where R ¹ represents C ₈ -C ₂₀ alkyl or C ₈ -C ₂₀ alkyl phenyl; R is alkylene having from 2 to about 4 carbon atoms, usually ethylene or propylene, m is zero or a number up to about 60, preferably less than 10, and more preferably about 4; and R ² is hydroxyl or the radical R ¹ —O- (RO) _m , where R ¹ and R are directly defined above and m is from 0 to about 30. If R ² is hydroxyl, these compounds are monoester. If R ² represents the radical R ¹ —O— (RO) _m , then these compounds are a diester. For use in the compositions of the present invention, mixtures of phosphoric acid esters or diesters of the formulas (52), (53) and / or (54) and a cationic surfactant, in particular alkylamine surfactants of the formulas (61), (62) are preferred ), (63) or (64). Mixtures of monoesters and diesters can also be used with polyoxyalkylene alkyl amines. If mixtures of monoesters and diesters are used, then the mass percentage of the monoester or monoesters exceeds the content of diester or diesters.

Other suitable anionic surfactants are fatty acid soaps, such as the tall oil ammonium salt and sodium stearate; alkyl sulfates, such as the sodium salt of C _8-10 alkanol sulfate and sodium oleyl sulfate; sulfonated oils such as sulfonated castor oil; alkoxylated alcohol sulfates such as sodium alkoxylauryl sulfate, ammonium alkoxylauryl sulfate and ammonium alkoxynonylphenol sulfate; sulfonates such as petroleum sulfonates, alkylbenzenesulfonates (e.g. sodium dodecylbenzenesulfonate (straight chain) or sodium dodecylbenzenesulfonates (branched chain), alkylnaphthalenesulfonates (e.g. sodium dibutylnaphthalenesulfonates, for example, sulfonates, for example, sulfonates, alkyl sulfates, dialkyl sulfosuccinates (e.g. sodium dioctyl sulfosuccinate) and monoalkyl sulfosuccinates and succinamides (e.g. disodium lauryl sulfosuccinate and disodium-N-alkyl sulfosuccinamate); sulfonated amides such as N-methyl-N-kokotaurat sodium, isethionates such as sodium cocoyl isethionate; sarcosinates such as N-lauroyl sarcosine, and phosphates such as alkyl ester ethoxylate phosphates and alkylaryl ether ethoxylated phosphates.

Examples of surfactants that can be used in accordance with the present invention are the following compounds:

and

Other surfactants that can be used in the herbicidal compositions and in concentrates of the present invention are N-acyl sarcosinates described in US Patent No. 5,985,798, which is incorporated herein by reference. Such surfactants are represented by the formula:

where R is C ₈ -C ₂₂ -N-acyl, preferably a C ₁₀ -C ₁₈ chain fatty acid, and X is a salt-forming cation, including alkali metal, ammonia or alkanolamine. More preferably, R is lauroyl, cocoyl, palmitoyl, myristoyl or oleoyl, and X is sodium, potassium, ammonium, isopropylamine or amino alcohol. Preferred sarcosinates are sodium lauroyl sarcosinate, sodium cocoyl sarcosinate and sodium myristoyl sarcosinate, which are commercially available under the trademark HAMPOSYL and supplied by Hampshire Chemical Corp.

Also suitable for use in the compositions and concentrates of the present invention are alkyl polyglycosides as described, for example, in US Pat. No. 6,117,820. As used herein, the term “alkyl glycoside” means mono- and polyalkyl glycosides. Glycosides have the formula:

where n denotes the degree of polymerization or the number of glycosyl groups, and R represents a branched or straight chain alkyl group having preferably from 4 to 18 carbon atoms, or a mixture of alkyl groups having an average length within the specified range. The number of glycosyl groups per alkyl group can vary, and derivatives of alkyl mono-, di- or polyglucose or saccharide can be obtained. Commercially available alkyl polyglycosides usually contain a mixture of derivatives, where n is an average. Preferably, n is from 1 to about 5, and more preferably from 1 to about 3. Typical alkyl glycosides are: a product sold under the trademark AL2042 (Imperial Chemical Industries PLC), where n is an average of 1.7 and R is a mixture of octyl (45%) and decyl (55%), a product sold under the trademark AGRIMUL PG2069 (Henkel Corp), where n is an average of 1.6, and R is a mixture of nonyl (20%), decyl (40 %) and undecyl (40%), and a product commercially available under the trademark BEROL AG6202 (Akzo Nobel), which is 2-ethyl-1-hexylglycoside.

Surfactants for use in solid concentrates of the "superdistributable" type are more preferred. Superdistributable surfactants are, but are not limited to, organosilicon and organofluorine surfactants. Organosilicon surfactants include polysiloxane. More specifically, organosilicon surfactants include polysiloxane, where at least one of the siloxane groups has a moiety containing one or more polyalkyleneoxy or polyalkyleneoxyalkyl groups.

Polysiloxane surfactants have the following formula:

where R ¹ represents C _n H _2n O (CH ₂ CH ₂ O) _m (CH ₂ CH (CH ₃ ) O) _q X, n is 0-6 and is from 0 to about 100, b is from 0 to about 10, m is from 0 to about 30, q is from 0 to about 30, X is hydrogen or a C _1-20 hydrocarbyl or C _2-6 acyl group, and the groups R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ , R ₁₀ independently represent a substituted or unsubstituted C _1-20 hydrocarbyl or nitrogen-containing group.

Basically, in preferred embodiments, n is 0-6, and is 0 to about 30, b is 0 to about 10, m is 0 to about 30, q is 0 to about 3, X is hydrogen or C _{1-6 is a} hydrocarbyl or C _2-6 acyl group, and the groups R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ , R ₁₀ independently represent a substituted or unsubstituted C _1-4 -hydrocarbyl or nitrogen-containing groups.

In one preferred embodiment of the invention, said polysiloxane is polyoxyethylene heptamethyltrisiloxane, where R ¹ is C _n H _2n O (CH ₂ CH ₂ O) _m (CH ₂ CH (CH ₃ ) O) _q X, n is 3 or 4, and 1b is 0, m is from 1 to about 30, q is 0, X represents hydrogen or a methyl, ethyl or acetyl group, and the groups R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ , R ₁₀ independently represent a substituted or unsubstituted C _1-4 hydrocarbyl or nitrogen-containing group.

In a preferred embodiment, in the formula for said polysiloxane surfactant, a is 1-5, b is 0-10, n is 3 or 4, m is 1 to about 30, q is 0, X is hydrogen or methyl, an ethyl or acetyl group, and the groups R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ , R ₁₀ represent methyl groups.

In another preferred embodiment of the invention, in the formula for said polysiloxane surfactant, a is 1-5, b is 0-10, n is 3 or 4, m is 4-12, q is 0, X is hydrogen or methyl or acetyl a group, and the groups R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ and R ₁₀ represent methyl groups.

In an even more preferred embodiment, in the formula for said polysiloxane surfactant, a is 1, b is 0, n is 3 or 4, m is 1 to about 30, q is 0, X is hydrogen or methyl, ethyl or an acetyl group, and the groups R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ and R ₁₀ represent methyl groups.

In another preferred embodiment of the invention, in the formula for said polysiloxane surfactant, a is 1, b is 0, n is 3, m is 8, q is 0, X is methyl, and the groups R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ and R ₁₀ represent methyl groups.

Trisiloxanes of the above formula are generally described in the literature relating to Crompton Corporation products and in US Pat. No. 3,553,777. Some of these trisiloxanes are ethoxylated organosilicon wetting agents sold by Crompton Corporation as silicone glycol copolymers under the trademark Silwet®. Both liquid organosilicon compounds and dry organosilicon compounds can be used in the composition of surfactants; and both are included in the scope of the present invention.

More preferred trisiloxanes are those commercially available in the United States or other countries and sold by Crompton Corporation under the trademarks Silwet® L-77, Silwet® 408 and Silwet® 800, by Dow-Corning under the trademarks Sylgard® 309, by Exacto, Inc. under the trademark Qwikwet® 100 and Goldschmidt under the trademark Breakthru S-240a. In the most preferred polyoxyethylene heptamethyltrisiloxanes, R ² is hydrogen.

The preferred surfactant composition used in the present invention contains about 75-100%, more preferably about 80-100%, by weight of polyoxyalkylenetrisiloxane. In this case, a mixture of more than one polyoxyalkylene trisiloxane can be used, where preferably the total amount of all polyoxyalkylene trisiloxanes present in the surfactant composition is defined above.

Polysiloxane surfactants may be combined with any of the surfactants described herein. In one embodiment, a polysiloxane of formula (59) is combined with an alkyl diphenyl oxide sulfonate having the formula:

where each of R independently represents a hydrocarbyl having from 1 to about 30 carbon atoms (preferably 6-10 carbon atoms), each n independently represents 0 or 1, each M ⁺ represents an agriculturally acceptable cation, and each n independently represents 0 or 1 when provided that the specified surfactant includes at least one sulfonate group. The specified cation may be ammonium (including alkylammonium and hydroxyalkylammonium), an alkali metal, alkaline earth metal or hydrogen. Such surfactant combinations typically include about 5-55 wt.% Polysiloxane surfactant and about 45-95 wt.% Diphenyl oxide sulfonate, and they are described in EP 1064844. Commercially available diphenyl oxide sulfonates are sodium alkyl diphenyl sulfonates sold under the trademark DOWFAX ^TM and supplied by Dow Chemical.

Organofluorine wetting agents that can be used in the present invention are organic molecules represented by the formula

where R _f represents a fluoroaliphatic radical, and G represents a group that contains at least one hydrophilic group, such as a cationic, anionic, nonionic or amphoteric group. R _f represents a fluorinated monovalent aliphatic organic radical containing at least four carbon atoms. Preferably, R _f is a saturated perfluoroaliphatic monovalent organic radical. However, hydrogen or chlorine may be present on the backbone as substituents. Although radicals containing a large number of carbon atoms can act adequately, compounds containing no more than about 20 carbon atoms are preferred, since large radicals usually do not make it possible to use fluorine efficiently, as can be done with shorter backbones . Preferably R _f contains about 5-14 carbon atoms.

Cationic groups that are used in the organofluorine wetting agents used in the present invention may include amine cationic groups or cationic quaternary ammonium groups. Such cationic hydrophilic amine groups and quaternary ammonium groups can have such formulas as NH ₂ , NHR ² , —N (R ² ) ₂ , - (NH ₃ ) X, - (NH ₂ R ² ) X, - (NH (R ²⁾ ₂ X), or - (N (R ²⁾ ₃ X), where X represents an anionic counterion such as halide, hydroxide, sulfate, bisulfate, acetate or carboxylate, and each R ² independently represents a C ₁ - ₁₈ alkyl group. Preferably X is a halide, hydroxide or bisulfate. Preferably, the cationogenic organofluorine wetting agents used in the present invention contain hydrophilic groups, which are cationogenic quaternary ammonium groups. Anionic groups that can be used in the organofluorine wetting agents used in the present invention include groups which, through ionization, can become anionic radicals. These anionic groups can have such formulas as —COOM, —SO ₃ M, —OSO ₃ M, —PO ₃ M ₂ , —PO ₃ NM, —OPO ₃ M _2, or —OPO ₃ NM, where M represents H, ion alkali metal, (NR ¹ ₄ ) ⁺ or (SR ¹ ₄ ) ⁺ , where each R ¹ independently represents H, either substituted or unsubstituted C ₁ -C ₆ alkyl. Preferably M is Na ⁺ or K ⁺ . Preferred anionic groups of organofluorine wetting agents used in the present invention are of the formula —COOM or —SO ₃ M.

Amphoteric groups that can be used in the organofluorine wetting agents used in the present invention are those containing at least one cationic group as defined above and at least one anionic group as defined above. Other suitable amphoteric groups are amine oxides.

Non-ionic groups that can be used in the organofluorine wetting agents used in the present invention are groups that are hydrophilic, but which are not ionized at a pH commonly used in agricultural practice. Nonionic groups may have formulas such as —O (CH ₂ CH ₂ ) _X H, where x is greater than 0, and preferably 1-30, —SO ₂ NH ₂ , —SO ₂ NHCH ₂ CH ₂ OH, —SO ₂ N (CH ₂ CH ₂ OH) ₂ , —CONH ₂ , —CONHCH ₂ CH ₂ OH, or —ON (CH ₂ CH ₂ OH) ₂ .

The cationogenic organofluorine wetting agents used herein are cationic fluorine-containing chemical compounds described, for example, in US Pat. No. 2764602, 4042522, 4069158, 4069244, 4090967, 4161590 and 4161602. The anionic fluororganic wetting agents used herein are anionic fluorine-containing chemicals a, as described, for example, in US Pat. Nos. 2803656, 3255131, 3450755 and 4090967. A detailed description of the above patents is incorporated herein by reference.

Several organofluorine wetting agents that can be used in the present invention are commercially available (3M) under the trademark Fluorad from 3M. Such agents are the anionic agents Fluorad FC-120, Fluorad FC-129 and Fluorad FC-99, the cationic agent Fluorad FC-750 and the nonionic agents Fluorad FC-170C, Fluorad FC-171 and Fluorad FC-430.

Representative surfactants of the above types are described in US Pat. Nos. 5,703,015, 5,750,468 and 5,389,598, which are hereby incorporated by reference in their entirety.

The surfactant component of the compositions of the present invention may, but not necessarily, comprise a glycol or glycol ester of the formula:

where R ⁴ in each of the groups x (R ⁴ O) independently represents a straight or branched C _2-6 alkylene group, x is from 1 to about 4, and R ⁵ represents hydrogen or a C _1-4 hydrocarbyl group. Considered glycols or glycol esters are, but are not limited to, monoethylene glycol, diethylene glycol, propylene glycol, or methyl, ethyl, n-propyl, butyl or tert-butyl ethers, dipropylene glycol or its methyl, ethyl, n-propyl, n-butyl or tert-butyl ethers, tripropylene glycol, its methyl, ethyl, n-propyl, n-butyl or tert-butyl ethers, 1,3-butanediol, 1,4-butanediol, 2-methyl-1,3-propanediol, 2, 2-dimethyl-1,3-propanediol, 2-methyl-1,3-pentanediol and 2-methyl-2,4-pentanediol.

Other nonionic surfactants may also be used, including, but not limited to, polyoxyethylene-polyoxypropylene block copolymers and alkyl polyglucosides. If necessary, cationic, anionic or amphoteric surfactants may also be used.

In an embodiment of the invention, said herbicidal compositions include at least one nonionic surfactant and at least one cationic surfactant, such as the surfactants described herein. Such combinations of surfactants are described in US Pat. No. 5,998,332, which is incorporated herein by reference.

Other cationic surfactants that can be used in the herbicidal compositions of the present invention are the surfactants described in US patent No. 5563111, 5622911, 5849663, 5863909, 5985794, 6030923 and 6093679, which are incorporated into this description by reference .

Surfactant compositions are generally intended to be mixed with a water-soluble herbicidal composition. Preferably, this surfactant composition is substantially free of water.

The surfactant composition of the present invention includes any combination of surfactants described above. This surfactant composition is particularly preferred for the preparation of preparations or concentrates containing potassium, diammonium, ammonium, sodium, monoethanolamine, n-propylamine, methylamine, ethylamine, hexamethylene diamine, dimethylamine and / or trimethyl sulfonium glyphosate.

The density of any glyphosate-containing composition of the present invention is preferably at least 1,050 grams / liter, and more preferably at least about 1,055, 1,060, 1,065, 1,070, 1,075, 1,080, 1,085, 1,090, 1,095 1,100, 1,105, 1,110 , 1,115, 1,120, 1,125, 1,130, 1,135, 1,140, 1,145, 1,150, 1,155, 1,160, 1,165, 1,170, 1,175, 1,180, 1,185, 1,190, 1,195, 1,200, 1,205, 1,210, 1,215, 1,220, 1,225, 1,230, 1,235 , 1,240, 1,245, 1,250, 1,255, 1,260, 1,265, 1,270, 1,275, 1,280, 1,285, 1,290, 1,295, 1,300, 1,305, 1,310, 1,315, 1,320, 1,325, 1,330, 1,335, 1,340, 1,345, 1,350, 1,355, 1,360 , 1,365, 1,370, 1,375, 1,380, 1,385, 1,390, 1,395, 1,400, 1,405, 1,410, 1,415, 1,420, 1,425, 1,430, 1,435, 1,440, 1,445 or 1,450 grams / liter.

To improve some of the properties of the obtained compositions of the present invention, other additives, adjuvants or ingredients may be incorporated into these compositions. Although the compositions of the present invention generally have good stability and viscosity without the addition of any other additives, the addition of a solubilizer (also commonly referred to as a turbidity enhancer or stabilizer) can greatly improve the properties of the compositions of the present invention. Suitable solubilizers that can be used in the new compositions of the present invention are, for example, cocoamine (Armeen C), dimethyl cocoamine (Arquad DMCD), cocoammonium chloride (Arquad C), PEG (2) cocoamine (Ethomeen C12) and PEG (5 ) Cocoamine (Ethomeen C15), all of which are manufactured by Akzo Nobel (California).

In addition, it was found that the addition of a C ₄ -C ₁₆ alkyl or arylamine compound or the corresponding Quaternary ammonium compound significantly increases the compatibility of certain glyphosate salts (e.g., potassium or isopropylamine salt) with surfactants that are greater or lesser degrees have little or little compatibility with a particular glyphosate loading. Suitable stabilizers are primary, secondary or tertiary C ₄ -C ₁₆ alkyl or arylamine compounds, or the corresponding quaternary ammonium compounds. Such stabilizers significantly increase the compatibility of certain glyphosate salts (e.g., potassium or isopropylamine salt) with surfactants that have more or less low compatibility or almost no such compatibility with a certain glyphosate loading. Suitable alkyl or arylamine compounds may also contain from about 0 to about 5 C ₂ -C ₄ alkylene oxide groups, and preferably ethylene oxide groups. Preferred alkylamine compounds include C ₆ -C ₁₂ alkyl amines having from 0 to 2 ethylene oxide groups. Similarly, etheroamine compounds having from 4 to 12 carbon atoms and from 0 to about 5 ethylene oxide groups, as well as the corresponding quaternary ammonium compounds, also increase the compatibility of these compositions.

In one embodiment of the invention, compounds that increase the compatibility of such surfactants are amine or quaternary ammonium salts of the formula:

or

or

or

where R ¹ represents a straight or branched alkyl group having from about 4 to 16 carbon atoms, R ² represents hydrogen, methyl, ethyl or - (CH ₂ CH ₂ O) _x H, R ³ represents hydrogen, methyl, ethyl or - ( CH ₂ CH ₂ O) _y H, where the sum of x and y does not exceed about 5; R ⁴ represents hydrogen or methyl; R ⁶ in each of the groups n (R ⁶ O) independently represents C ₂ -C ₄ alkylene; R ⁵ is hydrocarbylene or substituted hydrocarbylene having from 2 to about 6 carbon atoms; and A ^- is an agriculturally acceptable anion.

The present invention also relates to a method for controlling or controlling the growth of weeds or unwanted plants, comprising the steps of diluting a liquid concentrate in a suitable amount of water to form a reservoir mixture and applying a herbicidally effective amount of the reservoir mixture to the leaves of weeds or unwanted plants. Similarly, the present invention relates to a method for killing or controlling the growth of weeds or unwanted plants, comprising the steps of diluting a particulate concentrate in a suitable amount of water to form a reservoir mixture and applying a herbicidally effective amount of the reservoir mixture to the leaves of the weeds or unwanted plants.

In the method of using the herbicidal composition of the present invention, the composition is diluted in a suitable volume of water to obtain a solution for application, which is then applied to the leaves of the plant or plants at a rate of application sufficient to achieve the desired herbicidal effect. The application rate is usually expressed as the amount of glyphosate per unit of cultivated area, for example, in grams of the acid equivalent of glyphosate per hectare (g ke / ha). The term “desired herbicidal effect” usually or illustratively means at least 85% destruction of plants of a given species, which is measured by slowing down the growth of plants or their death after a certain period of time during which the glyphosate exerts its complete herbicidal or phytotoxic action on cultivated plants. Depending on the type of plant and growth conditions, this period of time can be only one week, but usually it is two weeks, necessary for the full realization of the effect of glyphosate.

The selection of application rates that are herbicidally effective for the composition of the present invention can be made by any agricultural specialist. It will be apparent to each person skilled in the art that the degree of herbicidal efficacy achieved by the practice of the present invention will depend on the condition of the individual plants, the weather and their growing conditions, as well as on the particular active ingredients used and their weight ratio in the composition. Regarding the use of glyphosate compositions, there is much information in the literature about suitable application rates for these compositions. Over the past two decades of the use of glyphosate and the studies on their use that have been published, a huge amount of information has accumulated on the basis of which suitable glyphosate application rates can be selected that have a herbicidal effect on specific types of plants at certain stages of their growth and at specific environmental conditions.

Glyphosate herbicidal compositions are used to kill a wide variety of weed plants found throughout the world, and it is obvious that in this respect potassium salts are no different from other glyphosate salts.

Examples of particularly important annual dicotyledonous plants that the composition of the present invention can be used to control include, but are not limited to, Theofrasti rodent (Abutilon theophrasti), amaranth (Amaranthus spp.), Burdock (Borreria spp.), Turnip, canola, Indian mustard, etc. (Brassica spp.), Commeline (Commelina spp.), Cycnotic stork (Erodium spp.), Annual sunflower (Helianthus spp.), Morning glory (Ipomoea spp.), Bunny cochia (Kochia scoparia), mallow (Malva spp.), highlander bindweed, highlander pepper, etc. (Polygonum spp.), Portulak (Portulaca spp.), Russian solyanka (Salsola spp.), Prickly brisket (Sida spp.), White mustard (Sinapis arvensis) and cocklebur (Xanthium spp.).

Particularly important annual monocotyledonous plants to which the composition of the present invention can be used are, but are not limited to, wild oat (Avena fatua), axonopus (Axonopus spp.), Roof fire (Bromus tectorum), blood dewdrop (Digitaria spp. ), cockerel millet (Echinochloa crus-galli), Indian elevine (Eleusine indica), chaff hard (Lolium multiflorum), rice (Oryza sativa), ottochloa (Ottochloa nodosa), paspalum (Paspalum notatum), canary fennel (Phanaris canaris). , foxtail (Setaria spp.), spinous wheat (Triticum aestivum) and corn (Zea mays).

Particularly important perennial dicotyledonous plants to control which the composition of the present invention can be used are, but are not limited to, wormwood (Artemisia spp.), Cobweed (Asclepias spp.), Cirsium arvense (Cirsium arvense), field bindweed (Convolvulus arvensis ) and hairy pueraria (Pueraria spp.).

Particularly important perennial monocotyledonous plants to control which the composition of the present invention can be used are, but are not limited to, corydum (Brachiaria spp.), Fingernail (Cynodon dactylon), eat edible (Cyperus esculentis), round eat (C. rotundus), creeping wheatgrass (Elymus repens), emperor cylindrical (Imperata cylindrica), chaff perennial (Lolium perenne), large millet (Panicum maximum), expanded paspalum (Paspalum dilatatum), reed (Phragmites spp.), wild sorghum ) and broadleaf rogos (Typha spp.).

Other particularly important perennials that the composition of the present invention can be used to control are, but are not limited to, horsetail (Equisetum spp.), Common bracken (Pteridium aquilinum), blackberry (Rubus spp.) And European ulex (Ulex europaeus )

If necessary, to obtain a composition intended for application, the consumer can mix one or more adjuvants with the composition of the present invention and with water for dilution. Such adjuvants may include additional surfactants and / or inorganic salts, such as ammonium sulfate, to further enhance hercicidal efficacy. However, under almost all conditions, the herbicidal method of the present invention provides acceptable efficacy in the absence of such adjuvants.

In a specifically contemplated method of using the composition of the present invention, after diluting the composition in water, the composition is applied to leaves of cultivated plants that have been genetically transformed or selected as glyphosate resistant, and at the same time to leaves of weeds or unwanted plants growing in close proximity to such crops. This method of application allows you to destroy weeds or unwanted plants, mainly without damaging cultivated plants. Cultivated plants that have been genetically transformed or selected as glyphosate resistant are plants whose seeds are sold by the Monsanto Company or with the permission of the Monsanto Company under the trademark Roundup Ready®. Such plants include, but are not limited to, various types of cotton, soy, canola, sugar beets, wheat, and corn.

Compositions for treating plants can be obtained by simply diluting the composition of the concentrate of the present invention in water. The application of the plant treatment composition to the leaves of the plants is preferably carried out by spraying using any standard means for spraying liquids, such as spray tips, sprayers or the like. The compositions of the present invention can be used in high-precision agricultural methods, where equipment is used to vary the amount of pesticide applied to different parts of the field depending on factors such as the particular type of plant, soil composition, etc. In one of the variants of such methods, for applying the desired amount of composition to different parts of the field, a global control system that works in conjunction with a sprayer can be used.

Preferably, immediately prior to application to the plant, the composition should be sufficiently diluted so that it can be easily applied using standard agricultural spray technology. In accordance with the present invention, preferred application rates may vary depending on a number of factors, including the type and concentration of the active ingredient and the type of plant. Suitable application rates for the aqueous composition on leaves under field conditions can range from about 25 to 1000 liters per hectare (l / ha) when applied by spraying. Preferred application rates for aqueous solutions are in the range of about 50 to 300 l / ha.

Many exogenous chemical compounds (including glyphosate herbicide) must be absorbed by the living tissues of the plant and move in the plant to produce the desired biological (e.g., herbicidal) effect. Thus, it is very important to apply the herbicidal composition in such a way that it does not lead to excessive damage and to an interruption of the normal functioning of the local tissue of the plant too quickly, as this may impede further movement of the herbicide into the tissue. However, some limited degree of local damage may not be significant or may even be desirable in terms of its effect on the biological effectiveness of some exogenous chemicals.

A large number of compositions of the present invention are illustrated in the examples below. Many glyphosate concentrate compositions had sufficient herbicidal efficacy when tested in greenhouses, which can serve as the basis for their subsequent field testing for the destruction of a wide variety of weeds under various processing conditions.

Definitions

As used herein, the terms “hydrocarbon” and “hydrocarbyl” mean organic compounds or radicals consisting solely of elements such as carbon and hydrogen. These radicals are alkyl, alkenyl, alkynyl and aryl radicals. Such radicals are also alkyl, alkenyl, alkynyl and aryl radicals substituted with other aliphatic or cyclic hydrocarbon groups such as alkaryl, alkenaryl and alkynaryl. Unless otherwise indicated, such radicals preferably contain from 1 to 30 carbon atoms.

As used herein, the term "hydrocarbylene" means radicals having bonds at their two ends with other radicals of an organic compound and consisting solely of elements such as carbon and hydrogen. These radicals are alkylene, alkenylene, alkynylene and arylene radicals. These radicals are also alkyl, alkenyl, alkynyl and aryl radicals substituted with other aliphatic or cyclic hydrocarbon groups, such as alkaryl, alkenaryl and alkynaryl. Unless otherwise indicated, such radicals preferably contain from 1 to 30 carbon atoms.

As used herein, the term “substituted hydrocarbyl radicals” means hydrocarbyl radicals which are substituted by at least one non-carbon atom, including radicals in which the carbon atom is replaced by a hetero atom, such as a nitrogen, oxygen, silicon, phosphorus, boron atom, sulfur or halogen. Such substituents are halogen, heterocyclo, alkoxy, alkenoxy, alkynoxy, aryloxy, hydroxy, protected hydroxy, ketal, acyl, acyloxy, nitro, amino, amido, cyano, thiol, acetal, sulfoxide, ester, thioester, ether, simple thioether, hydroxyalkyl, urea, guanidine, amidine, phosphate, amine oxide and quaternary ammonium salt.

As used herein, the term “substituted hydrocarbylene radicals” means hydrocarbylene radicals which are substituted by at least one non-carbon atom, including radicals in which the carbon atom is replaced by a hetero atom, such as a nitrogen, oxygen, silicon, phosphorus, boron atom, sulfur or halogen. Such substituents are halogen, heterocyclo, alkoxy, alkenoxy, alkynoxy, aryloxy, hydroxy, protected hydroxy, ketal, acyl, acyloxy, nitro, amino, amido, cyano, thiol, acetal, sulfoxide, ester, thioester, ether, simple thioether, hydroxyalkyl, urea, guanidine, amidine, phosphate, amine oxide and quaternary ammonium salt.

Unless otherwise indicated, the alkyl groups described herein are preferably lower alkyl containing from one to 18 carbon atoms in the main chain and up to 30 carbon atoms. They can be straight or branched or cyclic, and are methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, hexyl, 2-ethylhexyl and the like.

Unless otherwise indicated, the alkenyl groups described herein are preferably lower alkenyl containing from one to 18 carbon atoms in the main chain and up to 30 carbon atoms. They can be straight or branched or cyclic and can be ethenyl, propenyl, isopropenyl, butenyl, isobutenyl, hexenyl and the like.

Unless otherwise indicated, the alkynyl groups described herein are preferably lower alkynyl containing from one to 18 carbon atoms in the main chain and up to 30 carbon atoms. They can be straight or branched and are ethynyl, propynyl, butynyl, isobutynyl, hexynyl and the like.

The term “aryl”, used alone or as part of another group, means optionally substituted homocyclic aromatic groups, preferably monocyclic or bicyclic groups containing from 6 to 12 carbon atoms in the ring part, such as phenyl, biphenyl, naphthyl, substituted phenyl, substituted biphenyl or substituted naphthyl. More preferred aryl are phenyl and substituted phenyl.

As used herein, the term “aralkyl” means a group containing both alkyl and aryl structures, such as benzyl.

The alkyl, alkenyl, alkynyl, aryl and aralkyl groups used herein may be substituted by at least one non-carbon atom, including groups in which the carbon atom is replaced by a hetero atom, such as a nitrogen, oxygen, silicon, phosphorus, boron atom sulfur or halogen. Such substituents are hydroxy, nitro, amino, amido, cyano, sulfoxide, thiol, thioester, thioether, ester and ether, or any other substituent that can increase the compatibility of the surfactant and / or enhance its effectiveness in the composition potassium salt of glyphosate, without exerting a negative impact on the stability of the composition during storage.

As used herein, the terms "halogen" or "halogen", taken separately or as part of another group, mean chlorine, bromine, fluorine and iodine atoms. In surfactant compounds, fluorine substituents are most preferred.

Unless otherwise indicated, the term "hydroxyalkyl" means alkyl groups substituted with at least one hydroxy group, and such groups are bis (hydroxyalkyl) alkyl, tris (hydroxyalkyl) alkyl and poly (hydroxyalkyl) alkyl. Preferred hydroxyalkyl groups are hydroxymethyl (—CH ₂ OH), hydroxyethyl (—C ₂ H ₄ OH), bis (hydroxymethyl) methyl (—CH (CH ₂ OH) ₂ ) and tris (hydroxymethyl) methyl (—C (CH ₂ OH) ) ₃ ).

The term “cyclic” as used herein with respect to a particular group or part of another group, refers to a group having at least one closed ring, and such groups are alicyclic, aromatic (arene) and heterocyclic groups.

The terms “heterocyclo” or “heterocyclyl”, used here alone or as part of another group, mean optionally substituted fully saturated or unsaturated monocyclic or bicyclic aromatic or non-aromatic groups having at least one heteroatom in at least one ring, and preferably 5 or 6 atoms in each ring. The heterocyclo group preferably has 1 or 2 oxygen atoms, 1 or 2 sulfur atoms and / or 1-4 nitrogen atoms in the ring, and can be linked to the rest of the molecule via a carbon atom or a heteroatom. Examples of heterocyclo groups are heteroaromatic groups such as furyl, thienyl, pyridyl, oxazolyl, pyrrolyl, indolyl, quinolinyl or isoquinolinyl and the like, and non-aromatic heterocyclic groups such as tetrahydrofuryl, tetrohydrothienyl, piperidino and the like. Examples of substituents are one or more of the following groups: hydrocarbyl, substituted hydrocarbyl, keto, hydroxy, protected hydroxy, acyl, acyloxy, alkoxy, alkenoxy, alkynoxy, aryloxy, halogen, amido, amino, nitro, cyano, thiol, thioether, simple thioether, ketal, acetal, ester and ether.

The term “heteroaromatic”, used here alone or as part of another group, refers to optionally substituted aromatic groups having at least one heteroatom in at least one ring, and preferably 5 or 6 atoms in each ring. The heteroaromatic group preferably has 1 or 2 oxygen atoms, 1 or 2 sulfur atoms and / or 1-4 nitrogen atoms in the ring, and can be linked to the rest of the molecule via a carbon atom or a heteroatom. Examples of heteroaromatic groups are furyl, thienyl, pyridyl, oxazolyl, pyrrolyl, indolyl, quinolinyl or isoquinolinyl, and the like. Examples of substituents are one or more of the following groups: hydrocarbyl, substituted hydrocarbyl, keto, hydroxy, protected hydroxy, acyl, acyloxy, alkoxy, alkenoxy, alkynoxy, aryloxy, halogen, amido, amino, nitro, cyano, thiol, thioether, simple thioether, ketal, acetal, ester and ether.

The term “acyl”, used herein alone or as part of another group, means a group formed by removing a hydroxyl group from the —COOH group of an organic carboxylic acid, for example RC (O) -, where R is R ¹ , R ¹ O—, R ¹ R ² N-, or R ¹ S, R ¹ represents hydrocarbyl, heterosubstituted hydrocarbyl or heterocyclo, and R ² represents hydrogen, hydrocarbyl or substituted hydrocarbyl.

The term “acyloxy”, used herein alone or as part of another group, means an acyl group described above and linked by an oxygen bond (—O—), for example RC (O) O—, where R is as defined in the description of the term acyl.

If the description of structural elements, such as oxyethylene units or glucose units, uses the concept of maximum or minimum "average number", then for each specialist it is obvious that this concept means that the integer number of such units in individual molecules of a surfactant preparation usually varies within limits that may include integers that are higher than the maximum, or lower than the minimum "average". The presence in the composition of individual molecules of surfactants having an integer number of such units that is outside the established range for the "average" does not exclude this composition from the scope of the present invention, provided that the "average" is within the specified range and satisfies other requirements.

The term "storage stable", referring to the liquid concentrate of the present invention, means that this concentrate is not subjected to phase separation under the influence of temperatures up to about 50 ° C for 14-28 days, and preferably no glyphosate crystals or its form in this concentrate salt at a temperature of about 0 ° C for about 7 days (that is, this composition should have a crystallization temperature of 0 ° C or lower). For aqueous solution concentrates, storage stability at high temperatures is often indicated by a cloud point of about 50 ° C. or higher. To determine the cloud point of a composition, this composition is usually heated until the solution becomes cloudy, and then left under stirring to cool, while continuously monitoring its temperature. The cloud point is the temperature that is recorded at the moment when the solution begins to become transparent. A cloud point at 50 ° C or higher is generally considered the temperature acceptable for most commercial applications of the glyphosate aqueous solution concentrate composition. Ideally, the cloud point should be 60 ° C. or more, and the composition should remain stable at a temperature of at least about −10 ° C. for about 7 days without crystal growth, even in the presence of crystallization nuclei of glyphosate salt.

The term “surfactant” as used herein means a wide range of adjuvants that can be added to glyphosate herbicidal compositions to enhance herbicidal activity compared to glyphosate salt activity in the absence of such adjuvant, and also to increase stability, improve technological properties or other desirable properties. solution regardless of whether such an adjuvant meets the more traditional definition of “surfactant”.

EXAMPLES

The following examples are for illustrative purposes only and should not be construed as limiting the scope of the invention. These examples provide a better understanding of the present invention, its advantages, and some embodiments thereof.

The sprayable compositions described in the examples presented, in addition to the listed auxiliary ingredients, contain exogenous chemicals such as glyphosate potassium salt. The amount of exogenous chemical is chosen so that it provides the desired rate of application in grams per hectare (g / ha) when applied in a spray volume of 93 l / ha. For each composition, several application standards for exogenous chemicals were used. So, for example, if this is not specifically stated, when testing compositions for spraying, the concentration of exogenous chemicals varied in direct proportion to the rate of application of the exogenous chemical, and the concentration of auxiliary ingredients remained constant for all the different rates of application of the chemical used.

The concentrate compositions were tested by dilution, dissolution or dispersion in water to form spray compositions. In these spray formulations prepared from concentrates, the concentration of auxiliary ingredients varied depending on the concentration of the exogenous chemical.

The following examples illustrating the present invention describe tests that were performed in greenhouses and in the field to evaluate the relative herbicidal efficacy of glyphosate compositions. In these examples, unless otherwise specified, tests are carried out in greenhouses. Compositions used for comparison are described below:

Composition A drug Roundup® Ultra Roundup® Ultra (dry) Composition 5701 570 g / l IPA salt of glyphosate in an aqueous solution without the addition of a surfactant Composition 390K 391 g ke / l potassium salt of glyphosate in aqueous solution along with monoethoxylated amine as a surfactant Composition 360I 360 g ke / l IPA salt of glyphosate in water solution together with the system of surfactants described in US patent No. 5652197 Composition 480I 480 g ke / l IPA salt of glyphosate in aqueous solution along with ethoxylated ether-amine as a surfactant Composition 450IS 450 g ke / L IPA salt of glyphosate in aqueous solution along with ethoxylated ether-amine as the surfactant described in US Pat. No. 5,750,468 Composition 487K 487 g ke / l potassium salt of glyphosate in an aqueous solution together with 65 g / l alkoxylate cetete (2PO) (9EO) alcohol, 97 g / l ethoxylated (10EO) tallowamine and 85 g / l n-octylamine Composition 41I 41 wt.% IPA salt of glyphosate in an aqueous solution together with phosphoric acid ester and tallowamine as surfactants. This drug is sold by the Monsanto Company under the trademark Roundup® Ultra Ultramax dry Roundup® UltraMax (dry) Composition AMM-GLY1S Glyphosate ammonium salt (solid) with ethoxylated tallowamine as a surfactant Composition 540K 540 g ke / l potassium salt of glyphosate in aqueous solution together with an ether-amine surfactant Composition 360I 360 g ke / L IPA salt of glyphosate in aqueous solution together with 111 g / l ethoxylated tallowamine surfactant with 25 EO, 74 g / l polyoxyethylene-10 EO cetyl ether and 12 g / l myristyldimethyl amine oxide Composition 725K 725 g ke / l potassium salt of glyphosate in an aqueous solution without the addition of a surfactant Composition 540 KS 540 g ke / l potassium salt of glyphosate in aqueous solution together with 135 g / l ethoxylated ether-amine surfactant (M121) Composition 450I 450 g ke / L IPA salt of glyphosate in aqueous solution together with 168 g / l phosphoric acid ester and phosphoric acid diester as surfactants, as described in US Pat. No. 5,703,015 Composition AMM-GLY1S 91% ammonium glyphosate salt (solid) IPA composition (dry) IPA glyphosate (dry) Roundup® UltraMax 50 wt.% (455 g ke) of glyphosate IPA salt in aqueous solution together with a surfactant, supplied by Monsanto Company under the trademark Roundup® UltraMax Composition 470K 472 g ke / l potassium salt of glyphosate in an aqueous solution together with 117 g / l cocoamine-5 EO, 52 g / l isostearyl alcohol (10EO) and 13 g / l cocoamine Composition TD IQ Touchdown IQ®, which is an aqueous concentrate containing 28 wt.% Ke glyphosate diammonium salt and 8 wt.% alkyl polyglucoside surfactant Composition AMM-GLY3S A dry preparation containing 72% ammonium salt of glyphosate and 21% ethoxylated (20 EO) tallowamine Composition IPA-GLY An aqueous solution of IPA glyphosate containing C ₁₆ -C ₁₈ ethoxylate alcohol (20EO), ethoxylated (15 EO) -talloamine, cocoamidopropyl dimethylamide and tetrabutylammonium hydroxide Composition 650A A dry preparation containing 65 wt.% Ammonium salt of glyphosate and 14 wt.% Surfactant containing ethoxylated (15EO) tall oil dimethylammonium chloride and C ₁₆ -C ₁₈ ethanol alcohol (20EO) Composition 460I 46% IPA salt of glyphosate in aqueous solution without the addition of a surfactant Composition 479K 47.9% glyphosate potassium salt in aqueous solution without the addition of a surfactant Composition 540KS 40% glyphosate potassium salt in aqueous solution with 6% talloamine ethoxylate (10.5 EO), 5% ethoxylated cocoamine (2EO) and 0.6% citric acid

In the above compositions, various additives have been used. They can be identified in the following table:

A drug Trademark Manufacturer Chemical description S1 M-T1415E13-2 Tomah C ₁₄ -C ₁₅ alkyl- (EO) 13-dimethylpropylamine S2 MEAA5 Monsanto C18NMe (EO) 5.9H S3 MEAA11 Monsanto C18NMe (EO) 11H S4 MEAA7.5 Monsanto C18NMe (EO) 7.5H S5 Ethomeen C12 Akzo Ethoxylated Cocoamine 2EO S6 T45E18RA Tomah C ₁₄ -C ₁₅ (EO) 10-propylamine S7 T45E18DA Tomah C ₁₄ -C ₁₅ (EO) 13-propyldiamine S8 MEAA9.5 Monsanto C18NMe (EO) 9.5H S9 MEAA11 Monsanto C18NMe (EO) 11.1H S10 1816E20RA Tomah Ethoxylated (20 EO) cetyl / stearyletheriroamine S11 1816E10RA Tomah Ethoxylated (10 EO) cetyl / stearyletheriroamine S12 Witcamine 405 Witco PEG (5) -talloamine S13 1816E15RA Tomah Ethoxylated (15 EO) cetyl / stearyletheriroamine S14 Arquad 12-37W Akzo Dodecyl trimethammonium chloride S15 A mixture of cationogenic thalloamines and phosphoric acid esters described in US Pat. No. 5,703,015 S16 1816E10DA Tomah Ethoxylated (10 EO) cetyl / stearyl dipropyletheriroamine S17 T45R3E10RA Tomah C _14-15 O (PO) 3 (EO) 10-propylamine S18 Armeen DMCD Akzo N, N-dimethyl cocoamine S19 Ethomeen C15 Akzo Ethoxylated Cocoaamine (5) EO S20 Ethomeen C25 Akzo Ethoxylated Cocoaamine (25) EO S21 S-6122 Witco A mixture of coco-2EO-Quat and branched PEG (7) -C _12-15 alcohol S22 Witconol IS 100 Witco PEG (10EO) -iso-C ₁₈ alcohol S23 Witcamine 305 Witco PEG (5EO) Cocoamine S24 Armeen C Akzo coco (C ₁₂ -C ₁₈ unsaturated) primary amine S25 Phos A-100 Lambent Ethoxylated Silicone Phosphate Ether S26 Phos A-150 Lambent Ethoxylated Silicone Phosphate Ether S27 Phos A-200 Lambent Ethoxylated Silicone Phosphate Ether S28 Amine PD Lambent Branched silicone S29 Quat 400 M Lambent Siliconequat S30 M-T25E9-2 Tomah _12-15 C. PEG (9EO) dimetilefiroamin S31 Neodol 1-9 Shell PEG 9-C ₁₁ alcohol S32 APG 2067 Cognis (direct alkyl) polyglucoside S33 Tryfac 5560-A TDA-6 Cognis PEG 6-isotridecylphosphoric ester S34 AV 01 / 37-2 Clariant Monoethoxylated (7EO) Talloamine S35 AV 01 / 37-3 Clariant Monoethoxylated (15EO) Talloamine S36 E-14-2 Tomah bis- (2-hydroxyethyl) isodecyloxypropylamine S37 E-17-2 Tomah bis- (2-hydroxyethyl) isotridecyloxypropylamine S38 E-19-2 Tomah bis- (2-hydroxyethyl) (direct alkyloxypropyl) amine S39 E-14-5 Tomah poly (5) oxyethylene isodecyloxy propylamine S40 M-1618-E15-2 Tomah C _16-18 O (EO) 15-dimethylpropylamine S41 5595-120A Witco OPO ₃ C ₁₂ (EO) 5 S42 Arosurf 66 E10 Goldschmidt PEG-10-isostearyl ether S43 NA Witco /
Crompton Coquat 2 EO S43 Varonic K205 Goldschmidt Polyoxyethylene (5) -Cocoamine S44 Silwet L-77 Witco /
Crompton Heptamethyltrisiloxane 7EO-methyl ester S45 M-45P3E10-2 Tomah C _14-15 O (PO) 3 (EO) 10-dimethylpropylamine S46 T1415E18DA Tomah PEG 18-C _14-15 ether dipropylamine S47 APG 2069 Cognis Alkylpolyglucoside S48 AG 6202 Akzo nobel Alkylpolyglucoside S49 AV 01 / 37-3 Clariant Thalloamine Ethoxylate (15EO) S50 Hetoxol cs20 Global 7 C _16-18 ethoxylate-alcohol-20EO S51 MEAA 13 Monsanto Monoethoxylated alkylamine: C ₁₈ H ₃₇ NMe (13EO) H S52 1816P5E15PA Tomah C _16-18 propylene ether (5PO) (15EO) S53 HDTMH Sigma Hexadecyltrimethylammonium hydroxide S54 HDTMBr Alldrich Hexadecyltrimethylammonium bromide S55 1816P5E15DA Tomah C _16-18 ether diamine (5PO) (15EO) S56 M-T25E9-2 Tomah C _12-15 (9EO) dimethylethyroamine S57 M-91R3E10-2 Tomah C _9-11 dimethylethyroamine (3PO) (10EO) S58 91P3E10DA Tomah C _9-11 (3PO) (10EO) ether-diamine S59 VTAN Aidrich Benzyltrimethylammonium hydroxide S60 BTACI Aidrich Benzyltrimethylammonium chloride S61 Neodol 23-5 Shell C _12-15 ethoxylated (5EO) alcohol S62 Mackine 101 Mclntyre Cocoaminodipropyl Dimethylamine S63 Hetoxol CAW Global 7 C ₁₆ alcohol alkoxylate (5PO) (20EO) S64 S91R3E10RA Tomah C _9-11- alkoxylated propylamine, (3PO) (10EO) S65 Surfonic ™ AGM-550 Huntsman C _12-14 alkoxylated (1PO) propylamine- (5EO) ethoxylate S66 M-1816E15-2 Tomah C _16-18 -PEG 15 (EO) dimethylethyroamine S67 Pf 8000 Witco Ethoxylated Phosphoric Ester S68 TVAN Sigma Tetrabutylammonium hydroxide S69 AV 01 / 63-3 Clariant Talloamine Ethoxylate (15EO) S70 Ethomeen T25 Akzo Ethoxylated (15) Alkyltalloamine S71 NA Witco Ethoxylate C _16-18 alcohol (20EO) S72 Surfonic L68-20X Huntsman Ethoxylate C _16-18 alcohol (20EO) S73 Hetoxol CAW8 Global 7 Alkoxylate C ₁₆ alcohol (PO5) (EO20) S74 Agnique DF 6889 Cognis Anti-foaming silicone mixture S75 FloMo 1407 Witco /
Crompton Ethoxylated (20EO) alkyltalloamine S76 Surfonic T-15 Huntsman PEG15-Talloamine S77 Witcamine tam 150 Witco PEG15-Talloamine S78 AV 01 / 63-2 Clariant Monoethoxylated (15EO) Talloamine S79 AGM 550 Huntsman PEG 5-Etheriroamine S80 AV 01 / 96-2 Clariant Monoethoxylated Cocoamine (7EO) S81 AV 01 / 275-2 Clariant Monoethoxylated Stearylamine (11EO) S82 5595-125V Witco Alcohol ethoxylate C _12-14 (1.5PO) (8EO) S83 Witcamine TAM 105 Witco Talloamine Ethoxylate (10.5EO) S84 Ethoquad T25 Akzo nobel Ethoxylated (15 EO) Quaternary Ammonium Tall Oil Chloride S85 Brij 56 Sigma Stearyl alcohol ethoxylate (10 EA) S86 Emulgin l Cognis Ceteretpropoxylate (2PO) -ethoxylate (9EO) S87 NA Sigma Tetrahydrofuryl alcohol S88 Ammonyx SC 1485 Albemarie Myristyldimethylamine oxide S89 Isopar l Exxon Paraffin oil S90 AV 01 / 271-2 Monoethoxylated (11EO) Talloamine S91 Cocodimethylammonium Chloride

To test the compositions described in the examples in order to determine their effectiveness, the following methods were used, unless otherwise specified.

Seeds of plants of this type were sown in 85 mm square pots in a soil mixture that was previously sterilized with steam and into which fertilizers 14-14-14 NPK were previously applied with delayed release at a flow rate of 3.6 kg / m ³ . These pots were placed in greenhouses under conditions of subsoil irrigation. About one week after emergence, the seedlings were thinned, if necessary, including the removal of any unhealthy or abnormal plants, to create a homogeneous series of vegetative test vessels.

Throughout the test, the plants were kept in a greenhouse, which was illuminated for at least 14 hours a day. If natural light was not sufficient to maintain the required daily norm of illumination, then artificial illumination with an intensity of approximately 475 microeinstein was used to eliminate the deficit of light. The temperature was not precisely regulated, but the average daily temperature was approximately 27 ° C, and the night temperature was approximately 18 ° C. To ensure adequate soil moisture levels, plants were subjected to subsoil irrigation throughout the experiment.

Pots were used for various treatments in a randomized experiment with 6 repetitions of experiments. One series of pots was not processed, and it served as a control for subsequent comparison and evaluation of the effects of the treatments.

Glyphosate compositions can be applied by spraying with a weed control machine (sprayer) equipped with a 9501E nozzle calibrated to deliver a spray volume of 93 liters per hectare (l / ha) under a pressure of 166 kilopascals (kPa). After processing, the pots were returned to the greenhouse and kept there until the assessment.

Processing was carried out using dilute aqueous compositions. These compositions can be obtained in the form of ready-made spray formulations consisting only of their ingredients, or by dilution with water of previously prepared concentrate compositions.

To assess the herbicidal effectiveness, all plants used in the test were examined by one agricultural practitioner who recorded the percentage of dead plants and visually assessed the effectiveness of each treatment by comparison with untreated plants. Destruction of 0% means no effect, and the destruction of 100% indicates that all plants died. The destruction of 85% or more means that in most cases this drug is considered acceptable for normal use as a herbicide; however, in the tests conducted in the greenhouses and described in the examples, the compositions are usually used at such rates of consumption that give less than 85% destruction of plants, and this is done so that this composition can be easily differentiated (distinguished) from the compositions, having other levels of effectiveness. The recorded% killing of plants is the average value for each treatment carried out with several repetitions.

Example 1

The effect of low-mass acids on the effectiveness of the aminated alkoxylated alcohols of formulas (9) or (10) above was tested. For this, aqueous concentrate compositions were prepared containing glyphosate potassium salt in a concentration expressed in grams ke / liter and the auxiliary ingredients shown in table 1a.

Table 1a Composition Mr. KE glyphosate / l Component 1 % (w / v) Component 2 % (w / v) 346A8T 62.7 S1 2.0 - - 346B4E 62.7 S1 2.0 Acetic acid 0.1 346C0Z 62.7 S1 2.0 Phosphoric acid 0.15 346D2B 62.7 S1 2.0 Gluconic acid 0.35 346E9L 62.7 S1 2.0 Lactic acid 0.15 346F8T 62.7 S1 2.0 Oxalic acid 0.1 346G3S 62.7 S1 2.0 Fumaric acid 0.14 346H6Y 62.7 S1 2.0 Lemon acid 0.14

The compositions shown in table 1a, and the comparative compositions Roundup® UltraMax and composition 41I were applied to the plants of the Theofrasta abutilus (Abutilon theophrasti, ABUTH). The average results for all repetitions of experiments for each treatment are presented in table 1b.

Table 1b
% Destruction of ABUTH Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 346A8T 56.7 80.8 90.0 95.0 346B4E 58.3 80.8 90.0 93.3 346C0Z 53.3 80.8 90.8 95.5 346D2B 63.3 77.5 90.0 93.0 346E9L 50,0 80.0 87.5 93.8 346F8T 80.8 85.8 95.5 97.8 346G3S 67.5 77.5 89.2 91.7 346H6Y 61.7 81.7 88.3 94.7 Roundup® UltraMax 10.0 74,2 81.7 88.3 Composition 41I 23.3 76.7 85.0 93.8

Glyphosate potassium salt compositions containing oxalic acid and S1 had significantly higher efficacy than the standard Roundup® UltraMax composition and composition 41I, as well as composition 346A8T, which did not contain oxalic acid at all application rates (doses). All compositions containing or not containing dicarboxylic acids had a more effective herbicidal effect on the Teofrast rodent than Roundup® UltraMax compositions and composition 41I.

Example 2

A test was carried out on the herbicidal efficacy against Theophrastus tumeric by adding small organic acids to glyphosate potassium salt compositions containing aminated alkoxylated alcohols of the formulas (9) or (10). Table 2a describes the resulting aqueous compositions containing the glyphosate potassium salt at a concentration indicated in grams ke / liter and auxiliary ingredients. All components were added together and mixed in a batch shaker (loading) for 30 minutes at 60 ° C. Then all samples were cooled to room temperature and after 24 hours their stability was determined.

Table 2a Composition Glyphosate g / l Component 1 % (w / v) Component 2 % (w / v) 342A6J 62.7 S10 2.0 - - 342B9V 62.7 S1 2.0 Acetic acid 0.1 342C3H 62.7 S1 2.0 Phosphoric acid 0.15 342D7D 62.7 S1 2.0 Gluconic acid 0.35 342E7U 62.7 S1 2.0 Lactic acid 0.15 342F8K 62.7 S1 2.0 Oxalic acid 0.1 342G6R 62.7 S1 2.0 Fumaric acid 0.14 342H1A 62.7 S1 2.0 Lemon acid 0.14

The compositions shown in table 2A, and comparative compositions 570I and 41I were applied to the plants of the Theofrasta Abutilon (Abutilon theophrasti, ABUTH). The results, the average of all repetitions of experiments (replicas) for each treatment, are presented in table 2b.

Table 2b
% Destruction of ABUTH Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 342A6J 65 87.3 91.8 95.8 342B9V fifty 85.3 91.5 95.2 342C3H 50.3 84 92.3 94.8 342D7D 63.5 86.5 90.8 95.2 342E7U 54.7 87.7 92.8 94.7 342F8K 75.8 91.7 94.8 97.2 342G6R 70 84 92.2 94.8 342H1A 60 83 92.5 95.7 Composition 570I 0.8 14.2 37.5 60.5 Composition 41I 2.7 79.5 86.8 93.5

Composition 342F8K containing oxalic acid yielded the greatest destruction of the Theophrastus ropeway.

Example 3

A test was conducted on the effectiveness of the compositions of the potassium salt of glyphosate when citric and phosphoric acids were added to them. Table 3a describes the resulting aqueous compositions containing the glyphosate potassium salt indicated in grams ke / liter and auxiliary ingredients. All components were added together and mixed in a batch shaker for 30 minutes at 60 ° C. After incubation for 24 hours at room temperature, all samples remained stable, transparent and had a yellow color.

Table 3a Composition Glyphosate g / l Component 1 % (w / v) Component 2 % (w / v) 344A2G 62.7 S6 2.0 - - 344B8I 62.7 S7 2.0 - - 344C6R 62.7 S7 2.0 Lemon acid 0.08 344D9Z 62.7 S7 2.0 Lemon acid 0.24 344E7U 62.7 S7 2.0 Lemon acid 0.45 344F5X 62.7 S7 2.0 Phosphoric acid 0.10 344G5RT 62.7 S7 2.0 Phosphoric acid 0.20

The compositions shown in table 3A, and comparative compositions 570I and 41I were applied to the plants of the Theofrasta Abutilon (Abutilon theophrasti, ABUTH). The results, average for all replicates of experiments for each treatment, are presented in table 3b.

Table 3b
% Inhibition of ABUTH 14 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 342A2G 42.5 78.3 91.8 93.3 344B8I 17.5 66.7 86.2 93.2 344C6R 24.2 76.3 85.7 91 344D9Z 40 76.8 87.2 90.2 344E7U 40 76.7 87.2 91.7 344F5X 36.7 76.7 85.8 91.5 344G5T 30.8 74,2 85 91 Composition 570I 0 25 58.3 70.8 Composition 41I 35.8 74.7 86.8 94.3

The addition of low-mass acids, such as citric acid and phosphoric acid, did not significantly affect the effectiveness of the aminated alkoxylated alcohols of formula (5).

Example 4

A test was carried out on the effectiveness of oxalic acid compared with EDTA in relation to the plants of the teardrop Theofrast. Table 4a describes the resulting aqueous compositions containing the potassium salt of glyphosate. Glyphosate concentrations are indicated in grams ke / liter. Oxalic acid and EDTA were first dissolved in water, and then glyphosate potassium salt and surfactant were added. After that, the composition was placed in a batch shaker for 30 minutes at 60 ° C. 24 hours after cooling to room temperature, all samples remained stable, transparent and had a light yellow color.

Table 4a Composition Glyphosate g / l Component 1 % (w / v) Component 2 % (w / v) 381A9N 62.7 S1 2.0 Oxalic acid 0.2 381B3K 62.7 S1 2.0 Oxalic acid 0.4 381C4R 62.7 S1 2.0 EDTA 0.2 381D0Q 62.7 S1 2.0 EDTA 0.4 381E4I 62.7 S12 2.0 Oxalic acid 0.2 381F1A 62.7 S12 2.0 Oxalic acid 0.4 381G5C 62.7 S12 2.0 EDTA 0.2 381H8S 62.7 S12 2.0 EDTA 0.4

The compositions shown in Table 4a, Composition 725K, Composition 540I, and Roundup® UltraMax were applied to the plants of the Theofrasta cannabis (ABUTH). The results, the average of all repetitions of experiments for each treatment, are presented in table 4b.

Table 4b Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 381A9N 71.7 93.2 97.8 99 381B3K 74,2 90.5 99 99.5 381C4R 70 85.8 93.5 95.8 381D0Q 64,2 81.7 94.8 97.3 381E4I 66.7 86.7 93.3 98 381F1A 63.3 87.5 94.2 97.3 381G5C 49.2 72.5 86.7 89.2 381H8S 23.3 60.8 83.3 88.3 Composition 725K 0 9.2 36.7 61.7 Composition 570I 0 19.2 48.3 66.7 Roundup® UltraMax 25 75.8 90 94.7

Oxalic acid and EDTA in combination with _14-15 -PEG C 13 (EO) -efiroaminom showed similar efficacy. Oxalic acid compositions containing PEG 5-thalloamine showed higher efficacy than similar EDTA compositions. With _14-15 β-PEG 13 (EO) -ethiroamine yielded higher efficacy than similar compositions containing PEG 5-talloamine. All formulations except the composition with PEG 5-talloamine containing EDTA were more effective than the standard Roundup® UltraMax composition.

Example 5

A test was conducted on the effectiveness of various dicarboxylic acids with a cocoamine surfactant. Table 5a describes the resulting aqueous compositions containing the glyphosate potassium salt. Glyphosate concentrations are indicated in grams ke / liter. Dicarboxylic acids were added to these compositions in various weight ratios. The acids were first dissolved in water, and then the glyphosate potassium salt and surfactant were added. The compositions were mixed on a batch shaker for 30 minutes at 60 ° C. 24 hours after cooling to room temperature, all samples remained stable, transparent and colorless.

Table 5a Composition Glyphosate g / l Surface-active substance % (w / v) Dicarboxylic Acid (DC) % (w / v) Glyphosate: DK 611A5V 62.7 S5 2.9 - - - 611B9S 62.7 S5 2.0 Formic acid 0.15 40: 1 611C6L 62.7 S5 2.0 Oxalic acid 0.3 20: 1 611D3H 62.7 S5 2.0 Malonic acid 0.4 15: 1 611E8C 62.7 S5 2.0 succinic acid 0.4 15: 1 611F8K 62.7 S5 2.0 Glutaric acid 0.4 15: 1 611G1Z 62.7 S5 2.0 Adipic acid 0.5 12: 1 611H3J 63.7 S5 1,2 Oxalic acid 0.3 20: 1

The compositions shown in Table 5a and the reference compositions: composition 725K, composition 570I and Roundup® UltraMax, were applied to the plants of Theofrasta Abutilon (Abutilon theophrasti, ABUTH) and millet blackberry (Echinochloa crus-galli var. Frumentae, ECHCF). The results, average for all replicates of experiments for each treatment, are presented in tables 5b and 5c.

Table 5b
% Inhibition of ABUTH 14 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 611A5V 60 77.5 88.3 91.7 611B9S 46.7 80 88.3 90 611C6L 81.7 83.3 89.2 90 611D3H 47.5 82.5 87.5 90 611E8C 64,2 78.3 85.8 90.8 611F8K 47.5 82.5 85.8 90 611G1Z 75 80.8 86.7 87.5 611H3J 60 82.5 89.2 02.8 Composition 725K 20.8 70 80.8 82.5 Composition 570I 40 72.5 84.2 84.2 Roundup® UltraMax 72.5 87.5 90.8 92.2

Table 5c
% Inhibition of ECHCF 14 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 611A5V 55 60 66.7 82.5 611B9S 55 66.7 82.5 85.8 611C6L 55 63.3 78.3 82.5 611D3H 52,5 60 71.7 77.5 611E8C 55 60.8 65 74,2 611F8K 52,5 58.3 70.8 74,2 611G1Z 53.3 59.2 70 77.5 611H3J 52,5 60.8 73.3 80.8 Composition 725K 2,5 15.8 48.3 52,5 Composition 570I 15.8 40 fifty 55 Roundup® UltraMax 55 59.2 71.7 86.3

Oxalic acid enhanced the inhibitory effect on the plants of the Theophrastus canis, while other tested dicarboxylic acids did not. None of these dicarboxylic acids showed an increased inhibitory effect on cock millet. As can be seen from table 5b, some increased efficiency was observed when using adipic acid.

Example 6

The effect of iminodiacetic acid (IDA) compared with oxalic acid on the potassium glyphosate salt potency was tested. Table 6a describes the resulting aqueous concentrate compositions containing the glyphosate potassium salt. Glyphosate concentrations are indicated in grams ke / liter.

Table 6a Composition Glyphosate g / l Component 1 % (w / v) Component 2 % (w / v) 060AA3D 62 - - Oxalic acid 2.0 060AB8J 62 - - Oxalic acid 0.6 060AC3H 62 - - Iminodiacetic acid 2.0 060AD5N 62 - - Iminodiacetic acid 0.6 060AE7Q 62 S5 2.0 Oxalic acid 0.6 060AF6B 62 S5 2.0 Iminodiacetic acid 0.6 060AG0L 62 S5 2.0 - -

The compositions shown in Table 6a and comparative compositions: composition 725K, composition 570I and Roundup® UltraMax, were applied to the plants of Theofrasta Abutilon (Abutilon theophrasti, ABUTH) and millet blackberry (Echinochloa crus-galli var. Frumentae, ECHCF). The results, average for all replicates of experiments for each treatment, are presented in tables 6b and 6c.

Table 6b
% Inhibition of ABUTH 14 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 060AA3D 73.3 80 85.8 90 060AB8J 66.7 80 84.2 92.5 060AC3H 31.7 70 77.5 86.7 060AD5N 13.3 70 80 85.8 060AE7Q 71.7 85 87.5 97.5 060AF6B 55.8 80 87.5 94.8 060AG0L 60 74,2 87.5 92.5 Composition 725K 23.3 61.7 72.5 77.5 Composition 570I 36.7 65.8 77.5 84.2 Roundup® UltraMax 45 83.3 91.7 93.3 Table 6c
% Inhibition of ECHCF 14 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 060AA3D 10 30.8 43.3 fifty 060AB8J 13.3 40.8 54,2 55 060AC3H 14.2 30.8 55.8 57.5 060AD5N 20.8 39.2 51.7 62.5 060AE7Q 60 78.3 85 91.3 060AF6B fifty 76.7 80.8 82.5 060AG0L 59.2 70 84.2 92.5 Composition 725K 0.8 32,5 56.7 58.3 Composition 570I 14.2 thirty 54,2 57.5 Roundup® UltraMax 60 67.5 85.7 87.3

Oxalic acid was more effective in enhancing the herbicidal effect of glyphosate on the plants of the Theophrastus cannibal than iminodiacetic acid. To enhance the inhibitory effect of compositions containing oxalic acid and imidodiacetic acid, Ethomeen C12 was added to rooster millet.

Example 7

The ability of oxalic acid to enhance the potassium salt of glyphosate was evaluated in comparison with other known chelating compounds. Table 7a describes the resulting aqueous compositions containing the potassium salt of glyphosate. Glyphosate concentrations are indicated in grams ke / liter. Mass Relations KE glyphosate to sodium citrate, oxalic acid and EDTA were 2.2: 1, 2: 1 and 1.5: 1, respectively, and 22: 1, 20: 1 and 15: 1, respectively. The chelating compounds were first dissolved in water, and then the glyphosate potassium salt and surfactant were added. After that, the composition was placed in a batch shaker for 30 minutes at 60 ° C. 24 hours after cooling to room temperature, all samples remained stable and transparent.

Table 7a Composition Glyphosate g / l Component 1 % (w / v) 605A0X 64,2 DiK oxalic acid 4.09 605B5T 62.7 DiK oxalic acid 0.41 605C8U 63.6 EDTA 4.23 605D5A 62.7 EDTA 0.42 605E9I 63.6 Sodium citrate 2.68 605F2E 62.7 Sodium citrate 0.27

The compositions shown in Table 7a, composition 470K, composition 725K, composition 570I, and Roundup® UltraMax were applied to the plants of Theofrasta Abutilon (Abutilon theophrasti, ABUTH). The results, average for all replicates of experiments for each treatment, are presented in table 7b.

Oxalic acid was more effective in enhancing the action of glyphosate on the plants of the Theofrast rostrum compared with sodium citrate and EDTA. The effectiveness of the composition containing oxalic acid used in the relationship ke glyphosate: oxalic acid 2: 1 and 20: 1, was similar to the effectiveness of the standard composition Roundup® UltraMax and composition 470 K.

Example 8

The effectiveness of dicarboxylic acids was assessed together with diamines of formula (36) and glyphosate potassium salt. Table 8a describes the resulting aqueous compositions containing the glyphosate potassium salt. Glyphosate concentrations are indicated in grams ke / liter. The acids were first dissolved in water, and then the glyphosate potassium salt was added and the surfactant was melted in the resulting solution. The compositions were mixed on a batch shaker for 30 minutes at 60 ° C. 24 hours after cooling to room temperature, all samples remained stable, transparent and had a yellowish color.

The compositions shown in table 8a, and composition 725K, composition 570I and Roundup® UltraMax were applied to plants of the Theofrasta abutilus (Abutilon theophrasti, ABUTH). The results, the average of all repetitions of experiments for each treatment, are presented in table 8b.

Table 8b
% Inhibition of ABUTH 14 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 396A3J 53.3 79.2 87.5 90 396B5R 39.2 80.8 87.5 93 396C9A 53.3 80 85 91.5 396D3V 59.2 77.5 85 89.2 396E3R 71.7 85.8 86.7 92.2 396F9K 56.7 78.3 87.5 90 396G5B 52,5 80.8 85.8 89.2 396H7U 47.5 80.8 85.8 92.5 Composition 725K 6.7 63.3 75.8 80.8 Composition 570I 28.3 69.2 76.7 80.8 Roundup® UltraMax 60 80 88.3 92.5

Acetic, phosphoric, lactic, succinic, citric and gluconic acids did not give a significant increase in the effectiveness of their respective compositions against theophore theophra. The composition with oxalic acid was highly effective.

Example 9

The effectiveness of dicarboxylic acids was evaluated together with aminated alkoxylated alcohols of the formula (9). Table 9a describes the resulting aqueous compositions containing the potassium salt of glyphosate. Glyphosate concentrations are indicated in grams ke / liter. The acids were first dissolved in water, then the glyphosate potassium salt was added, and the surfactant was melted in the resulting solution. The compositions were mixed on a batch shaker for 30 minutes at 60 ° C. 24 hours after cooling to room temperature, all samples remained stable, transparent and had a yellowish color.

Table 9a Composition Glyphosate g / l Component 1 % (w / v) Component 2 (w / v) 390A7B 62.7 S1 2.0 Oxalic acid 0.2 390B8W 62.7 S1 2.0 succinic acid 0.26 390С3А 62.7 S1 2.0 Maleic acid 0.26 390D0K 62.7 S1 2.0 Fumaric acid 0.26 390E9D 62.7 S1 2.0 Succin amine acid 0.23 390F4G 62.7 S1 2.0 - - 390G4P 62.7 S30 2.0 Oxalic acid 0.26

The compositions shown in table 9a, and composition 725K, composition 570I and Roundup® UltraMax were applied to the plants of the teardrop Theofrasti (Abutilon theophrasti, ABUTH). The results, average for all replicates of experiments for each treatment, are presented in table 9b.

Table 9b
% Inhibition of ABUTH 15 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 390A7B 78.3 87.5 92.8 95.7 390B8W 70.8 84.2 91 93 390C3A 72.5 86.7 94.5 95 390D0K 75 85.8 93.5 98 390E9D 25.8 51.7 67.5 72.5 390F4G 70 85 90.8 94.5 390G4P 80 90.5 92.2 96.7 TD IQ 38.3 73.3 85 86.7 Composition 725K 0 2,5 21.7 56.7 Composition 570I 8.3 thirty 55 68.3 Roundup® UltraMax 41.7 75 88.3 90.8

Compositions with oxalic, maleic, and fumaric acids showed similar efficacy in inhibiting the plants of the Theophrastus cannibalis and had higher efficacy compared to the Roundup UltraMax standard. Succinamic acid showed an antagonistic effect with respect to the action of glyphosate when combined with C _14-15 -PEG 13 (EO) -dimethyletheramine used as a surfactant.

Example 10

The effect of adding oxalic acid to glyphosate in commercial standard formulations was evaluated in terms of their effect on Crescent Astragalus (CASOB). The assessment was carried out at three different mass ratios of ke glyphosate to oxalic acid, namely 2: 1, 10: 1 and 30: 1. The results, the average of all repetitions of experiments for each treatment, are presented in table 10a.

Table 10a
% Destruction of CASOB 18 days after processing Composition Glyphosate salt 200 g ke / ha 400 g ke / ha 800 g ke / ha Composition 725K TO 35 61.7 75 Roundup ultramax IPA 80 92.5 97.5 Roundup UltraMax: Oxalic Acid @ 2: 1 IPA 85 96.7 99.7 Roundup UltraMax: Oxalic Acid @ 10: 1 IPA 84.2 92.5 96.5 Roundup UltraMax: Oxalic Acid @ 30: 1 IPA 80.8 91.7 95 TD IQ di-NH ₄ 75 89.8 96.5 TD IQ: oxalic acid @ 2: 1 di-NH ₄ 82.5 90 96.5 TD IQ: oxalic acid @ 10: 1 di-NH ₄ 82.5 85.7 97.5 TD IQ: Oxalic Acid @ 30: 1 di-NH ₄ 77.5 85 97.5 Composition 540K TO 80.8 87.3 95 Composition 540K: oxalic acid @ 2: 1 TO 87.5 93.8 99,2 Composition 540K: oxalic acid @ 10: 1 TO 85.8 96.7 99.8 Composition 540K: oxalic acid @ 30: 1 TO 80 93.2 97.5

In all experiments, oxalic acid did not give a statistically significant increase in the action against astragalus sickle when mixed in a tank with a commercial standard composition. Oxalic acid significantly increased the effectiveness of compositions with a high loading of the IPA salt and glyphosate potassium salt.

Example 11

The effect of oxalic acid on amino esters was evaluated (7) and

dialkoxylated amines of the formula (39) and short chain EO-talloamine in a dilute composition of the IPA salt and glyphosate potassium salt. Glyphosate concentrations are indicated in grams ke / liter. All components were added together and the composition was mixed on a batch shaker for 30 minutes at 60 ° C. 24 hours after cooling to room temperature, all samples remained stable, transparent and had a yellowish color.

Table 11a Composition Glyphosate g / l Glyphosate salt Component 1 % (w / v) Component 2 (w / v) 366A1P 60.0 IPA S13 2.0 - - 366B4R 60.0 IPA S13 2.0 Oxalic acid 0.1 366S4K 62.7 TO S13 2.0 - - 366D5N 62.7 TO S13 2.0 Oxalic acid 0.1 366E3M 60.0 IPA S12 2.0 - - 366F0Q 60.0 IPA S12 2.0 Oxalic acid 0.2 366G6J 62.7 TO S12 2.0 - - 366H6D 62.7 TO S12 2.0 Oxalic acid 0.2

The compositions shown in table 11a, and comparative compositions: composition 725K, composition 570I and Roundup® UltraMax were applied to plants of the Theophrastus abutilus (Abutilon theophrasti, ABUTH). The results, average for all replicates of experiments for each treatment, are presented in table 11b.

All compositions containing oxalic acid showed higher efficacy compared to similar compositions not containing oxalic acid. All compositions 366A1P, 366B4R, 366C4K and 366D5N containing aminated alkoxylated alcohols of formula (9) with or without oxalic acid had higher efficacy than Witcamine 405 or standard glyphosate compositions. Compositions containing potassium salt or glyphosate IPA salt had similar efficacy.

Example 12

The effect of oxalic acid on the aminated alkoxylated alcohols of formula (9) was evaluated in compositions containing the IPA salt and glyphosate potassium salt. Aqueous compositions of concentrate 368A8F, 368B7I, 368C5O and 368D7Q containing potassium glyphosate salt were obtained. Aqueous compositions of 368E4V, 368F3C, 368G7G and 368H6L concentrate containing the glyphosate IPA salt were also prepared. Glyphosate concentrations are indicated in grams ke / liter. Compositions 368A8F and 368C5O additionally contained 0.5% oxalic acid. All components were added together, and the composition was mixed in a batch shaker for 1 hour at 60 ° C. 24 hours after cooling to room temperature, all samples remained stable, transparent and had a yellowish color.

Table 12a Composition Glyphosate g / l Component 1 wt.% Component 2 wt.% Component 3 wt.% 368A8F 484 S13 7.0 S5 3.0 S14 1,5 368B7I 63 S13 2.0 Oxalic acid 0.1 - - 368C5O 484 S1 7.0 S5 3.0 S14 1,5 368D7Q 63 S1 2.0 Oxalic acid 0.1 - - 368E4V 360 S13 10.0 S14 1,5 Oxalic acid 0.5 368F3C 360 S13 10.0 S14 1,5 - - 368G7G 60 S13 2.0 Oxalic acid 0.1 - - 368H6L 60 S13 2.0 - - - -

The compositions shown in table 12a, and comparative compositions: composition 725K, composition 570I and Roundup® UltraMax were applied to plants of the Theophrastus abutilus (Abutilon theophrasti, ABUTH). The results, average for all replicates of experiments for each treatment, are presented in table 12b.

Table 12b
% Inhibition of ABUTH Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 368A8F 61.7 81.7 88.3 95.8 368B7I 68.3 80.8 92.5 96.7 368C5O 70.8 80.8 90.8 95.3 368D7Q 78.3 93 96.3 99,2 368E4V 83.3 87.5 96 99,2 368F3C 65.8 80 92.5 97.2 368G7G 75 90 95.3 99,2 368H6L 70.7 85.8 93.3 99.7 Composition 725K 0 0 11.7 38.3 Composition 570I 0 0 21.7 42.5 Roundup ultramax 14.2 72.5 84.2 93.3

All 1816E15PA compositions containing or not containing oxalic acid showed higher efficacy compared to Roundup UltraMax. The greatest efficacy was found in compositions 368D7Q and 368Е4V, related to ke glyphosate to surfactant 3: 1 and 2.7: 1, respectively, and all compositions related to ke glyphosate to oxalic acid 60: 1.

Example 13

The effects of oxalic acid on various glyphosate salts were evaluated. Table 13a describes the obtained aqueous composition of the reservoir mixture containing potassium salt, IPA salt and glyphosate ammonium salt in mass ratios of 2: 1, 10: 1 and 30: 1, as well as 98% Aldrich oxalic acid (AL). The herbicidal activity of the reservoir mixture was analyzed compared to reservoir mixtures of the corresponding salts without the addition of oxalic acid.

Table 13a Composition Glyphosate salt Component 1 Glyphosate: SCH Composition 725K A TO - - Composition 725K B TO Oxalic acid 2: 1 Composition 725K S TO Oxalic acid 10: 1 Composition 725K D TO Oxalic acid 30: 1 Composition 570IA IPA - - Composition 570IB IPA Oxalic acid 2: 1 Composition 570IC IPA Oxalic acid 10: 1 Composition 570ID IPA Oxalic acid 30: 1 Composition AMM-GLY2S A NH ₄ - - Composition AMM-GLY2S B NH ₄ Oxalic acid 2: 1 Composition AMM-GLY2S C NH ₄ Oxalic acid 10: 1 Composition AMM-GLY2S D NH ₄ Oxalic acid 30: 1

Theofer Theofrast (Abutilon theophrasti, ABUTH) was grown and processed in accordance with the above standard methods. The results of the use of these compositions are presented in table 13a, were averaged over all replicates of experiments for each treatment and systematized in table 13b.

Table 13b
% Inhibition of ABUTH 15 days after treatment Composition 75 g ke / ha 100 g ke / ha 200 g ke / ha Composition 725K A 0 0 34.2 Composition 725K B 20.8 70.8 80 Composition 725K S 0 7.5 72.5 Composition 725K D 0 0 60 Composition 570IA 0.8 5 52,5 Composition 570IB 56.7 75.8 85 Composition 570IC 25.8 45 75.8 Composition 570ID 16.7 37.5 75 Composition AMM-GLY2S A 28.3 45.8 67.5 Composition AMM-GLY2S B 75 80 84.2 Composition AMM-GLY2S C 48.3 60.8 80 Composition AMM-GLY2S D 47.5 48.3 75.8

With the addition of oxalic acid, the potassium, IPA, and ammonium salts increased. The action of compositions containing glyphosate and oxalic acid was most effective in relation to ke glyphosate: oxalic acid, equal to 2: 1, and the least effective in relation to ke glyphosate: oxalic acid, equal to 30: 1.

Example 14

The effect of oxalic acid on glyphosate compositions containing surfactants was evaluated. Table 14a describes the resulting aqueous composition of the reservoir mixture containing potassium salt, IPA salt and glyphosate diammonium salt in ratios of 2: 1, 10: 1 and 30: 1, with 98% Aldrich oxalic acid (AL). Each of these glyphosate compositions contained various surfactant components. The herbicidal activity of the reservoir mixture was analyzed compared to reservoir mixtures of the corresponding salts without the addition of oxalic acid.

Table 14a Composition Glyphosate salt Surface-active substance Glyphosate: S Component 1 Glyphosate: SCH Composition 540K A K S65 4: 1 - - Composition 540K B K S65 4: 1 Oxalic acid 2: 1 Composition 540K C K S65 4: 1 Oxalic acid 10: 1 Composition 540K D K S65 4: 1 Oxalic acid 30: 1 Roundup UltraMax A IPA Patented - - - Roundup UltraMax B IPA Patented - Oxalic acid 2: 1 Roundup UltraMax C IPA Patented - Oxalic acid 10: 1 Roundup UltraMax D IPA Patented - Oxalic acid 30: 1 TD IQ-A di-NH ₄ Nonionic APG 3.6: 1 - - TD IQ-B di-NH ₄ Nonionic APG 3.6: 1 Oxalic acid 2: 1 TD IQ-C di-NH ₄ Nonionic APG 3.6: 1 Oxalic acid 10: 1 TD IQ-D di-NH ₄ Nonionic APG 3.6: 1 Sorrel
acid 30: 1

The compositions shown in table 14a, and the comparative composition 725K were applied to the plants of the Theofrasta Abutilon (Abutilon theophrasti, ABUTH). The results, average for all replicates of experiments for each treatment, are presented in table 14b.

Table 14b
% Inhibition of ABUTH 17 days after treatment Composition 75 g ke / ha 100 g ke / ha 200 g ke / ha Composition 540KA 12.5 38.3 72.5 Composition 540KV 76.7 84.2 91.7 Composition 540KS 70 79.2 87.5 Composition 540KD 34.2 76.7 84.2 Roundup UltraMax A 7.9 28 62.1 Roundup UltraMax B 80 85 90.8 Roundup UltraMax C 76.7 84.2 90.8 Roundup UltraMax D 70 78.3 87.5 TD IQ-A 16.7 26.7 65.8 TD IQ-B 75 84.2 90 TD IQ-C 45 77.5 87.5 TD IQ-D 41.7 67.5 85.8 Composition 725K ¹ 0 9.2 44,2 Composition 725K ² 15.8 46.7 80 ¹ The reservoir mixture obtained using the composition of 725K at 725 grams / l
² The reservoir mixture obtained using the composition of 725K at 445 grams / l

With the addition of oxalic acid, the effectiveness of all compositions increased. The action of compositions containing glyphosate and oxalic acid was most effective in relation to ke glyphosate: oxalic acid, equal to 2: 1. The Roundup UltraMax composition with oxalic acid had the greatest overall effectiveness, followed by the glyphosate potassium salt composition containing a cationic esteramine surfactant and TD IQ composition containing a nonionic alkyl polyglucoside.

Example 15

Evaluated the effectiveness of three commercially available glyphosate products and oxalic acid obtained in the form of reservoir mixtures. Table 15a describes the resulting aqueous composition of the reservoir mixture containing potassium salt, IPA salt and glyphosate diammonium salt in ratios of 2: 1, 10: 1 and 30: 1, as well as oxalic acid (AL). The herbicidal activity of the reservoir mixture was analyzed compared to reservoir mixtures of the corresponding salts without the addition of oxalic acid.

Table 15a Composition Glyphosate salt Component 1 Glyphosate: SCH Composition 540KA TO - - Composition 540KV TO Oxalic acid 2: 1 Composition 540KS TO Oxalic acid 10: 1 Composition 540KD TO Oxalic acid 30: 1 Roundup UltraMax A IPA - - Roundup UltraMax B IPA Oxalic acid 2: 1 Roundup UltraMax C IPA Oxalic acid 10: 1 Roundup UltraMax D IPA Oxalic acid 30: 1 TD IQ-A di-NH ₄ - - TD IQ-B di-NH ₄ Oxalic acid 2: 1 TD IQ-C di-NH ₄ Oxalic acid 10: 1 TD IQ-D di-NH ₄ Oxalic acid 30: 1

The compositions shown in table 15a and comparative composition 725K were applied to green bristle plants (SETVI). The results, average for all replicates of experiments for each treatment, are presented in table 15b.

Table 15b
% Inhibition of SETVI 14 days after treatment Composition 75 g ke / ha 100 g ke / ha 200 g ke / ha Composition 540KA 69.2 75 87.5 Composition 540KV 68.3 79.2 94.7 Composition 540KS 71.7 81.7 93 Composition 540KD 65 72.5 94 Roundup UltraMax A 70 72.5 86.7 Roundup UltraMax B 71.7 72.5 91.3 Roundup UltraMax C 71.7 78.3 89.2 Roundup UltraMax D 66.7 76.7 90.8 TD IQ-A 63.3 71.7 85 TD IQ-B 65.8 73.3 90.5 TD IQ-C 53.3 67.5 84.2 TD IQ-D 53.3 67.5 90.3 Composition 725K ¹ fifty 55 69.2 Composition 725K ² 70 72.5 86.7 ¹ The reservoir mixture obtained using the composition of 725K at 725 grams / l
² The reservoir mixture obtained using the composition of 725K at 445 grams / l

A significant increase in activity or antagonism using combinations with oxalic acid was not observed.

Example 16

Evaluated the effectiveness of three commercially available glyphosate products and oxalic acid obtained in the form of reservoir mixtures. Table 16a describes the resulting aqueous reservoir composition containing potassium salt, IPA salt and glyphosate diammonium salt in 2: 1, 10: 1 and 30: 1 ratios, as well as oxalic acid (AL). The herbicidal activity of the reservoir mixture was analyzed compared to reservoir mixtures of the corresponding salts without the addition of oxalic acid.

Table 16a Composition Glyphosate salt Component 1 Glyphosate: SCH Composition 540KA TO - - Composition 540KV TO Oxalic acid 2: 1 Composition 540KS TO Oxalic acid 10: 1 Composition 540KD TO Oxalic acid 30: 1 Roundup UltraMax A IPA - - Roundup UltraMax B IPA Oxalic acid 2: 1 Roundup UltraMax C IPA Oxalic acid 10: 1 Roundup UltraMax D IPA Oxalic acid 30: 1 TD IQ-A di-NH ₄ - - TD IQ-B di-NH ₄ Oxalic acid 2: 1 TD IQ-C di-NH ₄ Oxalic acid 10: 1 TD IQ-D di-NH ₄ Oxalic acid 30: 1

The compositions shown in table 16a, and comparative composition 725K were applied to annual chaff hard plants (LOLMG). The results, average for all replicates of experiments for each treatment, are presented in table 16b.

Table 16b
% Inhibition of LOLMG 13 days after treatment Composition 75 g ke / ha 100 g ke / ha 200 g ke / ha Composition 540KA 72.5 87.5 94 Composition 540KV 74,2 88 98.7 Composition 540KS 75 88.3 96.2 Composition 540KD 72.5 92.2 93.7 Roundup UltraMax A 71.7 88.5 92.2 Roundup UltraMax B 70 88 93.5 Roundup UltraMax C 73.3 85 94.7 Roundup UltraMax D 67.5 83.3 87.5 TD IQ-A 64,2 80 89.2 TD IQ-B 65 87.2 92.2 TD IQ-C 65 82.5 91.7 TD IQ-D 64,2 81.7 85 Composition 725K ¹ twenty 75.8 84.2 Composition 725K ² 71.7 88.5 92.2 ¹ The reservoir mixture obtained using the composition of 725K at 725 grams / l
² The reservoir mixture obtained using the composition of 725K at 445 grams / l

A significant increase in activity or antagonism using combinations with oxalic acid was not observed.

Example 17

Evaluated the effectiveness of three commercially available glyphosate products and oxalic acid obtained in the form of reservoir mixtures. Table 17a describes the resulting aqueous composition of the reservoir mixture containing the IPA salt and glyphosate diammonium salt in a ratio of 2: 1, 10: 1 and 30: 1, with oxalic acid (AL). The herbicidal activity of the reservoir mixture was analyzed compared to reservoir mixtures of the corresponding salts without the addition of oxalic acid.

Table 17a Composition Glyphosate salt Component 1 Glyphosate: SCH Roundup UltraMax A IPA - - Roundup UltraMax B IPA Oxalic acid 2: 1 Roundup UltraMax C IPA Oxalic acid 10: 1 Roundup UltraMax D IPA Oxalic acid 30: 1 TD IQ-A di-NH ₄ - - TD IQ-B di-NH ₄ Oxalic acid 2: 1 TD IQ-C di-NH ₄ Oxalic acid 10: 1 TD IQ-D di-NH ₄ Oxalic acid 30: 1

The compositions shown in table 16a and comparative composition 725K were applied to the plants of Theofrasta abutilus (Abutilon theophrasti, ABUTH) and millet blackberry (Echinochloa crus-galli var.frumentae, ECHCF). The results, the average of all replicates of experiments for each treatment, are presented in table 17b and 17C.

Table 17b
% Inhibition of ABUTH 15 days after treatment Composition 75 g ke / ha 100 g ke / ha 200 g ke / ha Roundup UltraMax A 5.8 56.7 82.5 Roundup UltraMax B 78.3 80 90 Roundup UltraMax C 71.7 79.2 89.2 Roundup UltraMax D 40 79.2 89.3 TD IQ-A 0 45 75 TD IQ-B 40 80 89.2 TD IQ-C 25.8 50.8 80 TD IQ-D 0 19.2 80 Composition 725K ¹ 0 5 29.2 Composition 725K ² 5.8 56.7 82.5 ¹ The reservoir mixture obtained using the composition of 725K at 725 grams / l
² The reservoir mixture obtained using the composition of 725K at 445 grams / l

Table 17c
% Inhibition of ECHCF 15 days after treatment Composition 75 g ke / ha 100 g ke / ha 200 g ke / ha Roundup UltraMax A 20.8 56.7 70 Roundup UltraMax B 44,2 60.8 67.5 Roundup UltraMax C 42.5 57.5 67.5 Roundup UltraMax D 38.3 57.5 67.5 TD IQ-A 6.7 thirty 62.5 TD IQ-B 25 35 63.3 TD IQ-C 23.3 45 60.8 TD IQ-D 29.2 41.7 62.5 Composition 725K ¹ 0 0 28.3 Composition 725K ² 20.8 56.7 70.0 ¹ The reservoir mixture obtained using the composition of 725K at 725 grams / l
² The reservoir mixture obtained using the composition of 725K at 445 grams / l

Oxalic acid enhanced the effectiveness of glyphosate on the Theofrasta rosacea, while the ratio of kef glyphosate to oxalic acid was 2: 1 most effective. Oxalic acid did not significantly increase the effect of glyphosate on rooster millet.

Example 18

The effectiveness of the surfactant Silwet L-77, used in combination with Roundup UltraMax and oxalic acid, in relation to morning glory was evaluated. Aqueous concentrate compositions containing the IPA salt of glyphosate in the form of Roundup UltraMax were prepared as reservoir mixtures with oxalic acid and with or without surfactant Silwet L-77 (S44) and are summarized in Table 18a.

Table 18a Composition Component 1 ke glyphosate: component 1 Component 2 ke glyphosate: component 2 Roundup UltraMax A - - - - Roundup UltraMax B - - S44 1000: 1 Roundup UltraMax C Oxalic acid 2: 1 - - Roundup UltraMax D Oxalic acid 10: 1 - - Roundup UltraMax E Oxalic acid 30: 1 - - Roundup UltraMax F Oxalic acid 2: 1 S44 1000: 1 Roundup UltraMax G Oxalic acid 10: 1 S44 1000: 1 Roundup UltraMax H Oxalic acid 30: 1 S44 1000: 1

The compositions shown in table 18a and comparative composition 725K were applied to morning glory plants (IPOSS). The results, the average of all repetitions of experiments for each treatment, are presented in table 18b.

Table 18b
% IPOSS inhibition 14 days after treatment Composition 300 g ke / ha 400 g ke / ha 600 g ke / ha Roundup UltraMax A 70 78.3 84.2 Roundup UltraMax B 80 80 82.5 Roundup UltraMax C 82.5 82.5 85 Roundup UltraMax D 80.8 83.3 85 Roundup UltraMax E 80 82.5 84.2 Roundup UltraMax F 84.2 82.5 85 Roundup UltraMax G 80.8 84.2 84.2 Roundup UltraMax H 80 84.2 85 Composition 725K ¹ 44,2 70 80 Composition 725K ² 70 78.3 84.2 ¹ The reservoir mixture obtained using the composition of 725K at 725 grams / l
² The reservoir mixture obtained using the composition of 725K at 445 grams / l

Oxalic acid used as an additive for the reservoir mixture in the ratio of ke glyphosate: oxalic acid 2: 1, 10: 1 or 30: 1, was equally effective in enhancing the effects of Roundup UltraMax on morning glory plants.

Example 19

The effect of oxalic acid on the effectiveness of glyphosate salts was evaluated. Aqueous compositions were prepared as indicated in table 19a. Glyphosate concentrations are given in g ke / liter.

Table 19a Composition Glyphosate g / l Glyphosate salt Component 1 mass / vol.% 053A9M 62 K Dipotassium oxalate 2.0 053B2C 62 K - - 053C5T 62 IPA Dipotassium oxalate 2.0 053D8N 62 IPA - - 053E2M 62 NH ₄ Dipotassium oxalate 2.0 053F1R 62 NH ₄ - - 053G0K 62 (NH ₄ ) ₂ Dipotassium oxalate 2.0 053H7A 62 (NH ₄ ) ₂ - -

The compositions shown in Table 19a and comparative compositions, namely, composition 725K, composition 570I and Roundup UltraMax, were applied to the plants of the Theofrasta Abutilon (Abutilon theophrasti, ABUTH) and the millet blackberry (Echinochloa crus-galli var.frumentae, ECHCF). The results, average for all replicates of experiments for each treatment, are presented in table 19b and 19c.

Table 19b
% Inhibition of ABUTH 16 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 053A9M 41.7 77.5 84.2 90 053B2C 14.2 62.5 78.3 81.7 053C5T 64,2 80.8 84.2 87.5 053D8N 16.7 65.8 78.3 79.2 053E2M 43.3 75 83.3 88.3 053F1R 27.5 62.5 70 79.2 053G0K 44,2 80.8 86.7 90.5 053H7A 17.5 61.7 75.8 77.5 Composition 725K 5 54,2 62.5 75.8 Composition 570I 6.7 58.3 73.3 80 Roundup ultramax twenty 80 85 90 Table 19c
% Inhibition of ECHCF 16 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 053A9M 26.7 45 47.5 51.7 053B2C 24.2 43.3 48.3 51.7 053C5T twenty 45.8 48.3 51.7 053D8N 21.7 42.5 49.2 51.7 053E2M 16.7 42.5 46.7 51.7 053F1R 10 40 47.5 52,5 053G0K 21.7 45 49.2 50.8 053H7A 11.7 31.7 45 49.2 Composition 725K 5 thirty 44,2 fifty Composition 570I 11.7 40 47.5 fifty Roundup ultramax 36.7 55 65.8 75.8

All compositions containing dipotassium oxalate exerted a significantly stronger effect on the theofer plants of Theofrast compared to similar compositions containing no oxalic acid and were more effective than the standard preparation Roundup® UltraMax. Dicalioxalate has been shown to enhance efficacy regardless of the type of glyphosate salt. Dicalioxalate was relatively ineffective in enhancing action against cock millet.

Example 20

The effects of oxalic acid and aminated alkoxylated alcohols of the formula (9), amino esters of the formula (7) and diamines of the formula (13) in solid compositions of the glyphosate ammonium salt were evaluated. For comparison, standard commercially available solid compositions were also prepared. The concentration of glyphosate ammonium salt for compositions 664A4D and 664C6G was 71% ke, and for composition 664B5T, this concentration was 65% ke. Oxalic acid and ammonium sulfate were added to the glyphosate ammonium salt, after which solvents were added. Then a molten surfactant was added. The composition was mixed in a mixer and extruded. The extrudate beads were dried at 50 ° C for 10 minutes. Then, the resulting material was sieved to obtain the desired granule size.

Table 20a Composition Component 1 wt.% Component 2 wt.% Component 3 wt.% 664A4D S64 10 S61 2 Oxalic acid 8 664V5T S13 8 S63 8 Ammonium sulfate 10 664C6G S62 10 S61 2 Oxalic acid 8

The compositions shown in table 20a, and comparative compositions: composition AMM-GLY2S, composition 570I and RoundupUltraMax, were applied to the plants of Theofrasta Abutilon (Abutilon theophrasti, ABUTH). The results, average for all replicates of experiments for each treatment, are presented in table 20b.

Table 20b
% Inhibition of ABUTH 16 days after treatment Composition 75 g ke / ha 100 g ke / ha 200 g ke / ha 400 g ke / ha 664A4D 80 81.7 96.5 99.5 664B5T 75 76.7 91.7 98.5 664C6G 80 82.5 90.8 99.3 Composition IPA Dry 79.2 80 93 99.5 Composition 470K 40.8 55 75 90.8 Composition AMM-GLY1S 34.2 42.5 80.8 94.5 Roundup ultra 75 81.7 95 98.5 Roundup UltraMax Dry 57.5 67.5 82.5 95.5 Composition AMM-GLY2S 0 8.3 50.8 79.2 Composition 570I 6.7 19.2 57.5 80 Roundup ultramax 56.7 60.8 81.7 93.8

Each of the three compositions was more effective than standard dry commercially available products.

Example 21

The effect of oxalic acid and oxalic acid salt on the effect of monoethoxylated alkylamine surfactants, taken alone or in combination with ethoxylated alcohol in glyphosate ammonium salt formulations, was evaluated. The molar ratio of oxalate: monoethoxylated alkylamine surfactant in each composition was at least 10: 1. Glyphosate concentrations for each composition were 62 g ke per liter. All components were added simultaneously and the composition was mixed in a batch shaker for one hour at 60 ° C. 24 hours after cooling to room temperature, all samples were stable, transparent and had a yellowish color.

Table 21a Composition Component 1 wt.% Component 3 wt.% Component 3 wt.% 071A5V S51 1,1 - - - - 071B7H S51 0.8 S50 0.3 - - 071C3S S51 1,1 - - Oxalic acid 0.9 071D0L S51 0.8 S50 0.3 Oxalic acid 0.9 071E1M S51 0.6 S50 0.4 - - 071F5W S51 0.6 S50 0.4 Oxalic acid 0.9 071G4B S51 1,1 - - NH ₄ oxalate 0.9 071H9M S51 0.6 S50 0.4 NH ₄ oxalate 0.9 071I6B S51 1,1 - - - - 071J5D S51 0.7 S50 0.5 - - 071K6J S51 1,1 - - Oxalic acid 0.9 071L1K S51 0.7 S50 0.5 Oxalic acid 0.9 071M3X S51 1,2 - - - - 071N7U S51 0.7 S50 0.5 - - 071O2W S51 1,2 - - Oxalic acid 0.8 071P9G S51 0.7 S50 0.5 Oxalic acid 0.8 071Q1A S49 1,1 - - - - 071R5V S49 0.9 S50 0.2 - - 071T6N S49 0.9 S50 0.2 Oxalic acid 0.9 071U8M S49 0.8 S50 0.3 - - 071V3Y S49 0.8 S50 0.3 Oxalic acid 0.9 071W2X S49 0.6 S50 0.4 - - 071X0D S49 0.6 S50 0.4 Oxalic acid 0.9 071Z2C S49 0.6 S50 0.4 NH ₄ oxalate 0.9 071AA2N S49 1,1 - - - - 071AB7H S49 0.9 S50 0.3 - - 071AD4N S49 0.9 S50 0.3 Oxalic acid 0.9 071AE3F S49 0.7 S50 0.5 - - 071AF7B S49 0.7 S50 0.5 Oxalic acid 0.9 071AG8O S49 1,2 - - - - 071AH6X S49 0.7 S50 0.5 - - 071AJ1Q S49 0.7 S50 0.5 Oxalic acid 0.8

The compositions shown in Table 21a and the comparative compositions AMM-GLY2S, AMM-GLY1S and Roundup UltraMax were applied to the Theofrasta plants (Abutilon theophrasti, ABUTH), and some of the compositions shown in Table 21a were applied to the blackberry plants of rooster millet (Echinochloa crus-galli var.frumentae, ECHCF). The results, the average of all replicates of experiments for each treatment, are presented in tables 21b and 21c.

Table 21b
% Inhibition of ABUTH 15 days after treatment Composition 75 g ke / ha 100 g ke / ha 200 g ke / ha 400 g ke / ha 071A5V 35 37.5 81.7 93.2 071B7H 20.8 47.5 83.3 95.3 071C3S 65 71.7 93 98.5 071D0L 81.7 85 93.3 99,2 071E1M 70.8 75 84.2 95.5 071F5W 83.3 88.3 90.7 99.7 071G4B 80 83.3 91.3 99.5 071H9M 80 85.8 93.5 99.3 071I6B 15.8 39.2 82.5 92.5 071J5D 25.8 72.5 85.8 96.3 071K6J 80 85 90 96.5 071L1K 81.7 86.7 90 97.5 071M3X thirty 61.7 86.7 91.7 071N7U 36.7 64,2 88.3 96.5 071O2W 80 85 91.1 96.5 071P9G 84.2 85 92.5 98.5 071Q1A 10 33.3 75 87.5 071R5V 27.5 thirty 78.3 87.5 071T6N 79.2 81.7 89.2 95.8 071U8M 48.3 78.3 80 90.8 071V3Y 84.2 85 90 96.7 071W2X 47.5 68.3 83.3 92.2 071X0D 82.5 82.5 91.7 98.7 071Z2C 85.8 86.7 94.2 98.7 071AA2N 24.2 52,5 80 88.3 071AB7H fifty 65.8 85 93.7 071AD4N 84.2 87.5 92.5 98.7 071AE3F 65.8 74,2 85.8 93 071AF7B 81.7 86.7 94.2 99,2 071AG8O fifty 65 84.2 87.5 071AH6X 55 64,2 85.8 94.7 071AJ1Q 84.2 86.7 92.5 99,2 Composition AMM-GLY2S 0 0 50.8 78.5 Composition AMM-GLY1S 0 28.1 75,2 87.8 Roundup ultramax 14.2 53.3 82.1 91.6

The Hetoxol CS20 surfactant with or without oxalic acid added to the monoethoxylated alkylamine surfactant gave a synergistic effect. All compositions containing a monoethoxylated alkylamine surfactant and oxalic acid or NH ₄ oxalate had a stronger effect than compositions not containing oxalate and standard glyphosate compositions.

Table 21c
% Inhibition of ECHCF 15 days after treatment Composition 75 g ke / ha 100 g ke / ha 200 g ke / ha 400 g ke / ha 071I6B twenty 57.5 75 85.5 071J5D 25 52,5 72.5 88 071K6J 9.2 fifty 67.5 75.8 071L1K 32,5 59.2 75 89.7 071M3X 45.8 59.2 70.8 83.3 071N7U 40 50.8 70 83.3 071O2W 28.3 45 64,2 75 071P9G 48.3 61.7 76.7 94.7 Composition AMM-GLY2S 0 5 35 60.8 Composition AMM-GLY1S 25 47.5 67.5 85 Roundup ultramax thirty 49.2 68.3 86.7

Hetoxol CS20 and a monoethoxylated alkylamine surfactant in combination with oxalic acid gave a significantly stronger effect compared to standard glyphosate preparations. A mixture of surface-active substances in its action was more effective than each individual surfactant.

Example 22

The effects of organic bases in combination with oxalic acid in reservoir mixtures containing the potassium salt of glyphosate and the alkyl ether-amine surfactant 1816P5E15PA (from Tomah) were evaluated. Glyphosate concentrations for each composition were 62.8 g ke per liter. Oxalic acid was first dissolved in water, then the molten surfactant and other components were added, and the resulting composition was mixed in a batch shaker for 30 minutes at 60 ° C. 24 hours after cooling to room temperature, all samples were stable, transparent and had a yellowish color.

Table 22a Composition Component 1 wt.% Component 2 wt.% Component 3 wt.% 666A9M S52 2.0 - - - - 666B6N S52 2.0 Oxalic acid 0.25 - - 666C4F S52 2.0 Oxalic acid 0.25 S53 0.25 666D3T S52 2.0 Oxalic acid 0.25 S53 0.5 666E0W S52 1.8 Oxalic acid 0.25 S53 0.75 666F7V S52 2.0 Oxalic acid 0.25 S53 one 666G3C S52 2.0 Oxalic acid 0.25 S54 1,2 666H1P S52 2.0 Oxalic acid 0.25 S54 0.6

The compositions shown in table 22a, and comparative compositions 725K, 570I, and Roundup UltraMax were applied to the plants of the Theofrasta Abutilon (Abutilon theophrasti, ABUTH). The results, the average of all repetitions of experiments for each treatment, are presented in table 22b.

Table 22b
% Inhibition of ABUTH 16 days after treatment Composition 75 g ke / ha 100 g ke / ha 200 g ke / ha 400 g ke / ha 666A9M 62.5 75 86.7 95.2 666B6N 75 80 92.5 95.7 666C4F 78.3 85 91.7 97.8 666D3T 76.7 81.7 87.5 98.3 666E0W 75 77.5 87.5 98 666F7V 73.3 80.8 90 96.2 666G3C 77.5 82.5 88.7 98.3 666H1P 72.5 82.5 90.8 97.2 Composition 725K 0 0 31.7 70 Composition 570I 0 0.8 45.8 67.5 Roundup ultramax twenty 40 80.8 93.3

The addition of oxalic acid to the reservoir mixture of an alkoxylated amine surfactant and glyphosate potassium salt led to some synergism. Even greater synergy was achieved with the addition of organic bases.

Example 23

The effects of organic bases in combination with oxalic acid in reservoir mixtures containing the potassium salt of glyphosate and the alkyl ether-amine surfactant 1816P5E15PA (from Tomah) were evaluated. Glyphosate concentrations for each composition were 62.8 g ke per liter. Oxalic acid was first dissolved in water, and then the molten surfactant and other components were added and the resulting composition was mixed in a batch shaker for 30 minutes at 60 ° C. 24 hours after cooling to room temperature, all samples were stable, transparent and had a yellowish color.

Table 23a Composition Component 1 wt.% Component 2 wt.% Component 3 wt.% 668A3C S52 2 - - - - 668B6H S52 2 Oxalic acid 0.25 - - 668C3P S52 2 Oxalic acid 0.25 S59 0.25 668D1Z S52 2 Oxalic acid 0.25 S59 0.5 668E0L S52 2 Oxalic acid 0.25 S59 0.75 668F8N S52 2 Oxalic acid 0.25 S59 one 668G2Q S52 2 - - S59 1,2 668H0B S52 2 Oxalic acid 0.25 S60 0.6

The compositions shown in table 23a, and comparative compositions 725K, 570I, and Roundup UltraMax were applied to the plants of the Theofrasta abutilus (Abutilon theophrasti, ABUTH). The results, the average of all repetitions of experiments for each treatment, are presented in table 23b.

Table 23b
% Inhibition of ABUTH 15 days after treatment Composition 75 g ke / ha 100 g ke / ha 200 g ke / ha 400 g ke / ha 668A3C 63.3 74,2 87.5 95.5 668B6H 68.3 74,2 88.3 96.3 668C3P 70.8 79.2 89.2 95.5 668D1Z 62.5 78.3 91.3 95.2 668E0L 74,2 79.2 88.3 96.8 668F8N 54,2 70 88.3 98.8 668G2Q 58.3 67.5 84.2 92.7 668H0B 59.2 72.5 87.5 94.5 Composition 725K 0 0 27.5 64,2 Composition 570I 0 0 35.8 70 Roundup ultramax 0 twenty 80 91.7

The addition of oxalic acid and an organic base to reservoir mixtures of an alkoxylated amine surfactant and glyphosate potassium salt led to a synergistic effect compared to all standard reference preparations.

Example 24

The effect of organic bases in combination with oxalic acid in reservoir mixtures containing the potassium salt of glyphosate in the presence or absence of alkoxylated alcohol Neodol 23-5 (from Shell) used as a surfactant was evaluated. Glyphosate concentrations for each composition were 62.8 g ke per liter. Oxalic acid was first dissolved in water, and then the molten surfactant and other components were added, and the resulting composition was mixed in a batch shaker for 30 minutes at 60 ° C. 24 hours after cooling to room temperature, all samples except 670G1P were stable, transparent and had a yellowish color. Composition 670G1P formed an unstable turbid dispersion.

Table 24a Composition Component 1 wt.% Component 2 wt.% Component 3 wt.% 670A2K S59 2 - - - - 670B7H S60 2 - - - - 670C3Z S60 1,6 - - Oxalic acid 0.8 670D1Q S60 1.4 - - Oxalic acid 0.7 670E0F S60 1,2 - - Oxalic acid 0.6 670F2M S60 one - - Oxalic acid 0.5 670G1P S60 0.8 S61 0.4 Oxalic acid 0.4 670H0K S59 0.8 S61 0.4 Oxalic acid 0.4

The compositions shown in table 24a, and comparative compositions 725K, 570I, and Roundup UltraMax were applied to the plants of the Theofrasta Abutilon (Abutilon theophrasti, ABUTH). The results, average for all replicates of experiments for each treatment, are presented in table 24b.

Table 24b
% Inhibition of ABUTH 14 days after treatment Composition 75 g ke / ha 100 g ke / ha 200 g ke / ha 400 g ke / ha 670A2K twenty 33.3 78.3 92.5 670B7H fifteen 35 72.5 85.8 670C3Z 61.7 64,2 86.7 91.7 670D1Q 47.5 63.3 85 93 670E0F 47.5 64,2 86.7 93.7 670F2M 35 78.3 86.7 93.8 670G1P 4.2 55.8 71.7 90 670H0K 0 41.7 83.3 93.7 Composition 725K 0 8.3 60 79.2 Composition 570I 0 16.7 fifty 81.7 Roundup ultramax 11.7 47.5 82.5 93.8

Benzyltrimethylammonium hydroxide and benzyltrimethylammonium chloride, used as separate surfactants, showed higher efficacy than the commercially available standard preparation Roundup UltraMax. The addition of oxalic acid led to an even greater increase in efficiency. The addition of Neodol 23-5 did not increase the effectiveness.

Example 25

The effect of organic bases in combination with oxalic acid in reservoir mixtures containing the glyphosate potassium salt was evaluated. Glyphosate concentrations for each composition were 62.4 g ke per liter.

Table 25a Composition Component 1 % wt. Component 2 % wt. 672A2B S59 2 - - 672B8J S59 2 Oxalic acid one 672C6G S59 1.7 Oxalic acid 0.8 672D0P S59 1,5 Oxalic acid 0.7 672E4F S59 1.3 Oxalic acid 0.6 672F7N S59 1,2 Oxalic acid 0.5 672G3X S59 one Oxalic acid 0.4

The compositions shown in table 25a, and comparative compositions: composition 725K, composition 570I and Roundup® UltraMax, were applied to the plants of Theofrasta Abutilon (Abutilon theophrasti, ABUTH). The results, average for all replicates of experiments for each treatment, are presented in table 25b.

Table 25b
% Inhibition of ABUTH 15 days after treatment Composition 100 g ke / ha 200 g ke / ha 400 g ke / ha 600 g ke / ha 672A2B 17.5 45.8 87.5 87.5 672B8J 45 80 91.7 96.3 672C6G 65 82.5 90.8 94.2 672D0P 62.5 85 92.5 95.8 672E4F 70.8 85 91.7 93.8 672F7N 43.3 83.3 92.3 94.2 672G3X 55 82.5 93 94.2 Composition 725K 0 1.7 thirty 78.3 Composition 570I 0 5 52,5 84.2 Roundup ultramax 26.7 80.8 91.7 95.5

The addition of oxalic acid and an organic base to the tank mixtures of glyphosate potassium salt gave a synergistic effect at all application rates. The greatest effect was observed with an organic base: oxalic acid ratio of 2: 1.

Example 26

The effect of oxalic acid on the effectiveness of the composition of the reservoir mixture containing the potassium salt of glyphosate and alkoxylated amine surfactants was evaluated. Glyphosate concentrations for each composition were 62.7 g ke per liter. Oxalic acid was first dissolved in water, and then a molten surfactant and glyphosate were added. Then this composition was mixed in a batch shaker for 30 minutes at 60 ° C. 24 hours after cooling to room temperature, all samples except 640E1A were stable, transparent and had a yellowish color. Composition 640E1A formed an unstable turbid dispersion.

Table 26a Composition Component 1 % wt. Component 2 % wt. 640A3C S40 2 Oxalic acid 0.2 640B7H S55 2 Oxalic acid 0.2 640C9M S1 2 Oxalic acid 0.2 640D3X S56 2 Oxalic acid 0.3 640E1A S16 2 Oxalic acid 0.25 640F5V S57 2 Oxalic acid 0.25 640G8J S58 2 Oxalic acid 0.25

The compositions shown in table 26a and comparative compositions: composition 725K, composition 570I and Roundup UltraMax, were applied to the plants of Theofrasta Abutilon (Abutilon theophrasti, ABUTH) and millet blackberry (Echinochloa crus-galli var.frumentae, ECHCF). The results, the average of all repetitions of experiments for each treatment, are presented in tables 26b, 26c and 26d.

Table 26b
% Inhibition of ABUTH 15 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 640A3C 80.8 90 98.3 98.3 640B7H 76.7 87.5 95.3 99 640C9M 70.8 89.7 91.3 95.2 640D3X 81.7 89.2 97.7 99,2 640E1A 52,5 85.8 93 95.3 640F5V 79.2 86.7 97 98.2 640G8J 75 85.8 95.3 97.8 Composition 725K 0 30.8 73.3 80.8 Composition 570I 5 fifty 77.5 83.3 Roundup ultramax 21.7 80 89.7 92.8

The addition of oxalic acid to the reservoir mixtures containing the alkoxylated amine and potassium salt of glyphosate gave a synergistic effect for all compositions except 640E1A. This difference in effectiveness due to the structures of surfactants was mediated by the addition of oxalic acid.

Table 26c
% Inhibition of ECHCF 15 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 640A3C 58.3 73.3 76.7 85.8 640B7H 57.5 70 79.2 83,2 640C9M 62.5 77.5 81.7 87.5 640D3X 62.5 75.8 82.5 88.3 640E1A 58.3 65 69.2 75.8 640F5V 60.8 74,2 88.8 92.3 640G8J 60 73.3 88.2 89.7 Composition 725K 6.7 44,2 50.8 62.5 Composition 570I 18.3 fifty 56.7 60.8 Roundup ultramax 53.3 67.5 75 81.7 Table 26d
% IPOSS inhibition 14 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 640A3C 80.8 86.7 86.7 87.5 640B7H 81.7 85 86.7 87.5 640C9M 83.3 83.3 85.8 87.5 640D3X 82.5 85.8 89.2 88.3 640E1A 83.3 85 87.5 88.3 640F5V 80.8 86.7 86.7 86.7 640G8J 82.5 85.8 85.8 87.5 Composition 725K 70 82.5 82.5 81.7 Composition 570I 70 82.5 83.3 84.2 Roundup ultramax 82.5 82.5 84.2 87.5

The addition of oxalic acid to the reservoir mixtures containing the alkoxylated amine and potassium salt of glyphosate gave a synergistic effect for all compositions except 640E1A. This difference in effectiveness due to the structures of surfactants was mediated by the addition of oxalic acid.

Example 27

The effectiveness of compositions with a high degree of loading of the potassium salt of glyphosate containing aminated alkoxylated alcohols of the formula (9) and phosphoric acid esters of the formula (5) was evaluated. The 609D4V and 609E8E aqueous concentrate compositions contained glyphosate IPA salt, and all other compositions contained glyphosate potassium salt. Glyphosate concentrations were expressed in g ke per liter. Oxalic acid was first dissolved in water, then KOH and a molten surfactant were added, and then glyphosate potassium salt was added. This composition was mixed in a batch shaker for 30 minutes at 60 ° C. 24 hours after cooling to room temperature, all samples were stable and transparent, with the exception of composition 609A8F, which was stable but turbid.

Table 27a Composition Glyphosate g / l Component 1 wt.% Component 2 wt.% Component 3 wt.% 609A8F 484 S40 6.0 S5 6.0 - - 609B4E 484 S1 6.0 S5 6.0 - - 609С2Р 484 S41 3.0 S12 7.0 S5 2.0 609D4V 434 S1 10.0 S43 1,5 - - 609E8E 434 S1 10.0 S43 1,5 Oxalic acid 1,2 609F2X 480 S41 4.0 S23 7.0 S5 3.0

The compositions shown in table 27a, and comparative compositions 725K, 570I, and Roundup UltraMax were applied to the plants of the Theofrasta Abutilon (Abutilon theophrasti, ABUTH). The results, the average of all repetitions of experiments for each treatment, are presented in table 27b.

Table 27b
% Inhibition of ABUTH 15 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 609A8F 61.7 83.3 92.5 94 609B4E 60 80.8 88.3 91.7 609C2P 65.8 80.8 87.5 90.5 609D4V 70 83.3 92.5 95.7 609E8E 81.7 90.5 97 98 609F2X 52,5 79.2 84.2 90.8 Composition 470K 55 79.2 83.3 92.2 Composition 725K 11.7 68.3 74,2 81.7 Composition 570I 38.3 67.5 80 84.2 Roundup ultramax 55.8 81.7 91.3 92.2

Composition 609E8E containing oxalic acid gave the greatest effectiveness, while its effectiveness exceeded the effectiveness of composition 609D4V, similar to the composition containing no oxalic acid.

Example 28

The effectiveness of oxalic acid and glyphosate salts in hard water was evaluated. Table 28a presents compositions of an aqueous concentrate containing potassium, IPA-, ammonium and diammonium salts of glyphosate. Glyphosate concentrations were expressed in g ke per liter.

Table 28a Composition Glyphosate g / l Glyphosate salt Component 1 % (w / v) Component 2 % (w / v) 045A1B 62 K Oxalic acid 0.41 - - 045B6E 62 K Oxalic acid 0.41 S5 2.0 045C4R 62 IPA Oxalic acid 0.41 - - 045D2J 62 Roundup ultramax Oxalic acid 0.41 - - 045E9D 62 di-NH ₄ Oxalic acid 0.41 - - 045F8K 62 TD IQ Oxalic acid 0.41 - - 045G2W 62 TD IQ - - - - 045H7A 62 Roundup ultramax - - - - 045I4R 62 Composition 725K - - S5 2.0

The compositions shown in table 28a and compositions 045G2W, 045H7A and 045I4R, used as comparative compositions, were applied to the plants of the Theofrasta Abutilon (Abutilon theophrasti, ABUTH). The compositions shown in Table 28a were re-applied with 500 ppm. CaCl ₂ added to simulate hard water. The results, average for all replicates of experiments for each treatment, are presented in table 28b.

Table 28b
% Inhibition of ABUTH 15 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 045A1B 31.7 58.3 75 85 045A1B-H fifteen 31.7 55 78.3 045B6E 53.3 70 83.3 86.7 045B6E-H 66.7 75 81.7 90 045C4R 55 60 75 83.3 045C4R-H 25 46.7 51.7 71.7 045D2J 75 83.3 85 93.3 045D2J-H 6.7 35 fifty 80 045E9D 60 65 81.7 86.7 045E9D-H 41.7 48.3 53.3 70 045F8K 60 80 83.3 86.7 045F8K-H 36.7 fifty 60 83.3 045G2W 53.3 63.3 76.7 85 045G2W-H 40 48.3 53.3 81.7 045H7A 66.7 75 81.7 90 045H7A-H 41.7 58.3 66.7 88.3 045I4R 51.7 60 78.3 85 045I4R-H 3.3 35 68.3 85

The addition of 500 ppm CaCl ₂ reduced the activity of all the compositions. Oxalic acid significantly increased the effectiveness of all compositions.

Example 29

The effect of hard water on the effectiveness of oxalic acid and glyphosate salts was evaluated. Table 29a presents compositions of an aqueous concentrate containing potassium, IPA-, ammonium and diammonium salts of glyphosate. Glyphosate concentrations were expressed in g ke per liter.

Table 29a Composition Glyphosate g / l Glyphosate salt Component 1 %
(w / v) Component 2 %
(w / v) 045A7R 62 K Oxalic acid 0.41 - - 045B3U 62 K Oxalic acid 0.41 S5 2.0 045C3X 62 IPA Oxalic acid 0.41 - - 045D0L 62 Roundup ultramax Oxalic acid 0.41 - - 045E4C 62 di-NH ₄ Oxalic acid 0.41 - - 045F7J 62 TD IQ Oxalic acid 0.41 - - 045G2K 62 TD IQ - - - - 045H5F 62 Roundup ultramax - - - - 045I3P 62 Composition 725K - - S5 2.0

The compositions shown in table 29a and compositions 045G2K, 045H5F and 045I3P, used as comparative compositions, were applied to the plants of the Theofrasta Abutilon (Abutilon theophrasti, ABUTH). The compositions shown in Table 29a were re-applied with 500 ppm CaCl ₂ added to simulate hard water. The results, average for all replicates of experiments for each treatment, are presented in table 29b.

Table 29b
% Inhibition of ABUTH 16 days after treatment Composition 100 g ke / ha 150 g ke / ha 300 g ke / ha 400 g ke / ha 045A7R 41.7 60 76.7 86.7 045A7R-H 13.3 thirty 63.3 66.7 045B3U 60 63.3 83.3 86.7 045B3U-H 53.3 63.3 73.3 83.3 045C3X 66.7 71.7 80 86.7 045C3X-H 26.7 55 61.7 71.7 045D0L 80 81.7 85 91.7 045D0L-H 35 46.7 55 78.3 045E4C 65 66.7 78.3 85 045E4C-H 43.3 56.7 60 68.3 045F7J 66.7 70 83.3 86.7 045F7J-H 46.7 56.7 61.7 83.3 045G2K 58.3 71.7 78.3 83.3 045G2K-N 46.7 60 75 76.7 045H5F 61.7 70 85 90 045H5F-H 45 58.3 68.3 83.3 045I3P 48.3 66.7 75 88.3 045I3P-H 0 40 65 83.3

The addition of 500 ppm CaCl ₂ reduced the activity of all the compositions. Oxalic acid significantly increased the effectiveness of all compositions.

Example 30

The effects of oxalic acid along with various surfactants on morning glory plants were evaluated. Table 30a shows dilute aqueous compositions of glyphosate potassium salt in hard water (i.e., all compositions contained 500 ppm calcium chloride). Glyphosate concentrations were expressed in g ke / liter. Mass Relations KE glyphosate to surfactant was approximately 3: 1, and the mass ratio ke glyphosate to oxalic acid was approximately 60: 1, 40: 1, 30: 1, 24: 1, 20: 1 or 3: 1. Oxalic acid was dissolved, glyphosate potassium salt and molten surfactant were added. Then the composition was mixed in a batch shaker for 30 minutes at 60 ° C. 24 hours after cooling to room temperature, all samples remained stable, transparent and colorless.

Table 30a Composition Glyphosate g / l Component 1 % (w / v) Component 2 % (w / v) 383A2T 62.7 S1 2.0 Sorrel
acid 0.2 383B7K 62.7 S1 2.0 - - 383C4D 62.7 S13 2.0 Sorrel
acid 0.2 383D3E 62.7 S13 2.0 - - 383E8N 62.7 S5 2.0 Sorrel
acid 0.4 383F6V 62.7 S5 2.0 - - 383G7Q 62.7 S18 2.0 Sorrel
acid 0.4 383H0O 62.7 S18 2.0 - -

The compositions shown in table 30a, composition 725K, composition 570I and Roundup® UltraMax were applied to morning glory plants (IPOSS). The results, average for all replicates of experiments for each treatment, are presented in table 30b.

Table 30b
% Inhibition of IPOSS 15 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 383A2T 0 9.2 17.5 41.7 383B7K 0 1.7 7.5 28.3 383C4D 0 28.3 65 77.5 383D3E 0 3.3 7.5 twenty 383E8N 4.2 18.3 25 55 383F6V 0 5 7.5 46.7 383G7Q 2,5 twenty 26.7 49.2 383H0O 0 0 1.7 13.3 Composition 725K 0 0 2,5 10 Composition 570I 0 0 2,5 18.3 Roundup ultramax 0 1.7 7.5 20.8

All compositions containing oxalic acid are more effective than compositions not containing oxalic acid. The addition of oxalic acid to the 725K composition led to a significant increase in the inhibitory effect on the morning glory weed.

Example 31

The effect of oxalic acid along with surfactants on the plants of the Theofrasta cannabis was evaluated. Table 31a presents aqueous compositions of a concentrate containing potassium glyphosate salt. Glyphosate concentrations were expressed in g ke / liter. Oxalic acid was dissolved, then the glyphosate potassium salt was added, and then the molten surfactant was added. Then the composition was mixed in a batch shaker for 30 minutes at 60 ° C. 24 hours after cooling to room temperature, all samples were stable, transparent and had a yellow color.

Table 31a Composition Glyphosate g / l Component 1 % (w / v) Component 2 % (w / v) 383A7U 62.7 S1 2.0 Oxalic acid 0.2 383B5D 62.7 S1 2.0 - - 383C3N 62.7 S13 2.0 Oxalic acid 0.2 383D8H 62.7 S13 2.0 - - 383E5A 62.7 S5 2.0 Oxalic acid 0.4 383F0L 62.7 S5 2.0 - - 383G5K 62.7 S18 2.0 Oxalic acid 0.4 383H1Z 62.7 S18 2.0 - -

The compositions shown in table 31a, composition 725K, composition 570I and Roundup UltraMax were applied to the plants of the Theofrasta cannabis (ABUTH). The results, average for all replicates of experiments for each treatment, are presented in table 31b.

Table 31b
% Inhibition of ABUTH 17 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 383A2T 69.2 88.3 90.8 95.5 383B7K 46.7 80.8 85.8 93.3 383C4D 66.7 88.3 93.3 95 383D3E 55.8 85 90 96.8 383E8N 33.3 80 89.2 91.7 383F6V 5 35 75 83.3 383G7Q 5 33.3 75.8 89.2 383H1Z 0 9.2 60.8 75.8 Composition 725K 0 0 24.2 45 Composition 570I 0 0 45.8 64,2 Roundup ultramax 5 79.2 82.5 89.2

Surfactants, C _14-15 PEG 13 (EO) -ethiroamine and PEG 15 (EO) ether, in combination with oxalic acid gave the greatest efficiency.

Example 32

The effectiveness of oxalic acid was evaluated along with surfactants in glyphosate potassium salt formulations. Table 32a presents the aqueous composition of the concentrate containing the glyphosate potassium salt. Glyphosate concentrations were expressed in g ke / liter. Oxalic acid was dissolved, then the glyphosate potassium salt was added, and then the molten surfactant was added. Then the composition was mixed in a batch shaker for 30 minutes at 60 ° C. 24 hours after cooling to room temperature, all samples were stable, transparent and had a yellow color.

Table 32a Composition Glyphosate g / l Component 1 % (w / v) Component 2 % (w / v) 383A2T 62.7 S1 2.0 Oxalic acid 0.2 383B7K 62.7 S1 2.0 - - 383C4D 62.7 S13 2.0 Oxalic acid 0.2 383D3E 62.7 S13 2.0 - - 383E8N 62.7 S5 2.0 Oxalic acid 0.4 383F6V 62.7 S5 2.0 - - 383G7Q 62.7 S18 2.0 Oxalic acid 0.4 383H0O 62.7 S18 2.0 - -

The compositions shown in table 32a, composition 725K, composition 570I and Roundup UltraMax were applied to prickly brisket plants (SIDSP). The results, average for all replicates of experiments for each treatment, are presented in table 32b.

Table 32b
% Inhibition of brisket sternum 18 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 383A2T 65.8 78.3 85 90 383B7K 55 75 85 90 383C4D 65 80.8 88.3 92.2 383D3E 65 79.2 90 93 383E8N 68.3 80 82.5 85.8 383F6V 60.8 78.3 80 83.3 383G7Q 50.8 75 80.8 85.7 383H0O 21.7 66.7 77.5 81.7 Composition 725K 10 38.3 63.3 70 Composition 570I 40 55 67.5 77.5 Roundup ultramax 55 75 82.5 93.3

The addition of oxalic acid, taken in the relationship ke-glyphosate: oxalic acid, constituting 30: 1 or 15: 1, led to an increase in efficiency.

Example 33

The effect of oxalic acid on the potassium efficiency of glyphosate and aminated alkoxylated alcohols of the formula (5) was evaluated. The aqueous concentrate compositions contained glyphosate potassium salt at a concentration expressed in g ke / liter and the auxiliary ingredients shown in table 33a. The acids were first dissolved in water, and then the glyphosate potassium salt and surfactant were added. The compositions were mixed in a batch shaker for 30 minutes at 60 ° C. 24 hours after cooling to room temperature, all samples were stable, transparent and had a yellow color with the exception of composition 359B3W, which was unstable and cloudy.

Table 33a Composition Glyphosate g / l Component 1 % (w / v) Component 2 % (w / v) 359A5L 62.7 S1 2.0 - - 359B3W 62.7 S1 0 Oxalic acid 2.0 359C3M 62.7 S1 2.0 Oxalic acid 0.1 359D8C 62.7 S1 2.0 Oxalic acid 0.15 359E7B 62.7 S1 2.0 Oxalic acid 0.2 359F4P 62.7 S1 2.0 Oxalic acid 0.25 359G4S 62.7 S1 2.0 Oxalic acid 0.3 359H2L 62.7 S1 2.0 Oxalic acid 0.2

The compositions shown in table 33a, and comparative compositions: composition 725K, composition 570I, Roundup UltraMax and composition 41I, were applied to the plants of Theofrasta Abutilon (Abutilon theophrasti, ABUTH). The results, the average of all repetitions of experiments for each treatment, are presented in table 33b.

Table 33b
% Inhibition of ABUTH 14 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 359A5L 55 80 90 97.8 359B3W 65 79.2 84.2 86.7 359C3M 80 92.7 97.3 99.5 359D8C 79.2 96.3 98 99.3 359E7B 85.5 95.3 99 99.8 359F4P 81.7 90.8 96.5 98.5 359G4S 81.7 95.5 96.3 99,2 359H2L 80 95.3 96.2 99 Composition 725K 0 10 32,5 70.8 Composition 570I 0 fifteen 54,2 75.8 Roundup ultramax 23.3 80 87.5 92.2 Composition 41I 31.7 81.7 94.7 96.8

All compositions containing oxalic acid and a surfactant had higher efficacy than the standard Roundup® UltraMax glyphosate formulations and composition 41I. Reduced effectiveness was given only composition 359B3W, not containing a surfactant. Compositions containing oxalic acid in an amount of from 0.1 to 0.3% in combination with C _14-15 PEG13 (EO) etherodimethylpropylamine had similar efficacy.

Example 34

The effects of oxalic acid were evaluated; ethoxylamine ethoxylated on a single chain used as a surfactant; and glyphosate potassium salt per Indian mustard. Table 34a presents diluted aqueous glyphosate potassium salt formulations. Glyphosate concentrations were expressed in g ke / liter. Mass Relations KE glyphosate to surfactant was approximately 3: 1, and the mass ratio ke glyphosate to oxalic acid was approximately 60: 1, 40: 1, 30: 1, 24: 1, 20: 1 or 3: 1. All components were added simultaneously and the composition was mixed in a batch shaker for 30 minutes at 60 ° C. 24 hours after cooling to room temperature, all samples were stable, transparent and colorless with the exception of composition 369B6S, which was unstable and cloudy.

Table 34a Composition Glyphosate g / l Component 1 % (w / v) Component 2 % (w / v) 359A0G 62.7 S1 2.0 - - 369B6S 62.7 S1 0 Oxalic acid 2.0 369C7K 62.7 S1 2.0 Oxalic acid 0.1 369D4W 62.7 S1 2.0 Oxalic acid 0.15 369E6U 62.7 S1 2.0 Oxalic acid 0.2 369F9I 62.7 S1 2.0 Oxalic acid 0.25 369G3A 62.7 S1 2.0 Oxalic acid 0.3 369H5C 62.7 S1 2.0 Oxalic acid 0.2

The compositions shown in table 34a and comparative compositions 725K, 570I and Roundup® UltraMax were applied to Indian mustard plants (BRSJU). The results, average for all replicates of experiments for each treatment, are presented in table 34b.

Table 34b
% Inhibition of BRSJU 23 days after treatment Composition 200 g ke / ha 400 g ke / ha 600 g ke / ha 800 g ke / ha 359A0G 66.7 81.7 86.7 89.2 369B6S 61.7 72.5 73.3 75 369C7K 54,2 79.2 83.3 85 369D4W 71.7 78.3 88.3 90 369E6U 65 77.5 84.2 90 369F9I 62.5 80.8 81.7 85 369G3A 69.2 80 81.7 85 369H5C 65 78.3 80.8 82.5 Composition 725K 5 9.2 52,5 66.7 Composition 570I 5 36.7 72.5 75 Roundup ultramax 46.7 76.7 78.3 80 Composition 41I 48.3 76.7 78.3 83.3

Oxalic acid did not give a significant increase in effectiveness against Indian mustard. The effectiveness of the composition did not depend on the concentration of oxalic acid.

Example 35

The efficacy of oxalic acid and aminated alkoxylated alcohols of the formula (5) was evaluated in dilute glyphosate potassium salt formulations. Table 35a presents aqueous concentrate compositions containing the glyphosate potassium salt. Glyphosate concentrations are expressed in g ke / liter. All components were added simultaneously and the composition was mixed in a batch shaker for 30 minutes at 60 ° C. 24 hours after cooling to room temperature, the compositions 376A3X, 376B5I and 376C4W were stable, transparent and colorless. All other drugs were unstable and cloudy.

Table 35a Composition Glyphosate g / l Component 1 % (w / v) Component 2 % (w / v) 376A3X 62.7 S16 2.0 - - 376B5L 62.7 S16 2.0 Oxalic acid 0.05 376C4W 62.7 S16 2.0 Oxalic acid 0.1 376D0S 62.7 S16 2.0 Oxalic acid 0.2 376E6D 62.7 S16 2.0 Oxalic acid 0.3 376F5G 62.7 S16 2.0 Oxalic acid 0.4 376G8N 62.7 S16 2.0 Oxalic acid 0.5 376H7A 62.7 S16 2.0 Oxalic acid 0.6

The compositions shown in table 35a, and comparative compositions: composition 725K, composition 570I and Roundup UltraMax, were applied to the plants of the Theofrasta Abutilon (Abutilon theophrasti, ABUTH). The results, average for all replicates of experiments for each treatment, are presented in table 35b.

The results showed that a high degree of effectiveness of compositions with a high loading of glyphosate potassium salt can be achieved by adding oxalic acid to C ₁₆ - ₁₈ PEG 10 (EO) -surface-active substances containing a polyamine head group. Polyamine head groups are known to produce stable high loading compositions. The addition of oxalic acid leads to an increase in the effectiveness of C _16-18 PEG 10 (EO) -etherdipropylamine surfactants used in relation to ke glyphosate surfactant constituting 3: 1, while the ratio of ke was most effective. glyphosate to oxalic acid, comprising 20: 1, and the effectiveness of compositions containing oxalic acid exceeded the effectiveness of the compared standard preparations.

Example 36

The effectiveness of oxalic acid in combination with the aminated alkoxylated alcohols of the formula (9) in diluted glyphosate potassium salt compositions was evaluated. Table 36a describes the resulting aqueous concentrate composition with potassium glyphosate salt. Glyphosate concentrations are expressed in g ke / l. Oxalic acid was dissolved, a molten surfactant was added, and then the glyphosate potassium salt was added. After that, the composition was mixed in a batch shaker for 30 minutes at 60 ° C. 24 hours after cooling to room temperature, all samples were stable, transparent and colorless with the exception of composition 618B8F, which was unstable, cloudy and formed a precipitate.

Table 36a Composition Glyphosate g / l Component 1 % (w / v) Component 2 % (w / v) 618A3D 62.7 S30 2.0 - - 618B8F 62.7 - - Oxalic acid 2.0 618C7S 62.7 S30 1.9 Oxalic acid 0.1 618D2K 62.7 S30 1.8 Oxalic acid 0.2 618E1U 62.7 S30 1,6 Oxalic acid 0.4 618F4P 62.7 S30 1.4 Oxalic acid 0.6 618G6W 62.7 S30 1,2 Oxalic acid 0.8 618H1Q 62.7 S30 1,0 Oxalic acid 1,0

The compositions shown in table 36a, composition 725K, composition 570I and Roundup UltraMax were applied to the plants of the Theofrasta Abutilon (Abutilon theophrasti, ABUTH). The results, the average of all repetitions of experiments for each treatment, are presented in table 36b.

Oxalic acid gave an increase in efficiency compared with only one system of surfactants and provided a higher efficiency than the standard preparation Roundup UltraMax. An increase in the concentration of oxalic acid and a simultaneous decrease in the concentration of surfactant led to an increase in efficiency. Relations KE glyphosate: oxalic acid, constituting 30: 1, 15: 1, 7.5: 1 and 6: 1, gave similar efficacy. The combination of surfactant and oxalic acid showed a synergistic effect, since the combination at an equal concentration of the ingredients was more effective than each of them taken separately.

Example 37

The effect of oxalic acid on the effectiveness of reservoir mixtures of monoethoxylated alkylamine and amino esters of formula (7) in combination with the potassium salt of glyphosate was evaluated. In addition, the efficacy of oxalic acid, used both for pretreatment and as an adjuvant for the reservoir mixture with monoethoxylated alkylamine surfactants, was evaluated. Preliminary treatment with oxalic acid was carried out one hour before the introduction of aqueous concentrate compositions. Table 37a describes the resulting aqueous concentrate compositions containing the glyphosate potassium salt in a concentration expressed in g ke / liter and additional ingredients. Composition 026Z2H contains the IPA salt of glyphosate.

Table 37a Composition Glyphosate g / l Component 1 % (w / v) Component 2 % (w / v) 026A2W 62 S8 2.0 Oxalic acid 0.41 026B3B 62 S8 2.0 - - 026C5Z 62 S11 2.0 Oxalic acid 0.40 026D5K 62 S11 2.0 - - 026E0A - - - Oxalic acid 0.40 026Z2H 62 - - Oxalic acid 0.40

The compositions shown in table 37a and comparative compositions: composition 725K, composition 570I, Roundup UltraMax and composition 41I, were applied to the plants of Theofrasta Abutilon (Abutilon theophrasti, ABUTH). The results, the average of all repetitions of experiments for each treatment, are presented in table 37b.

A composition of UltraMax with added 0.4% oxalic acid gave the greatest efficiency. Pretreatment of the theophore plants of Theophrastus with oxalic acid one hour before treatment with glyphosate and monoethoxylated alkylamine or aminated alkoxylated alcohol compositions did not give a significant increase in efficiency compared to the efficiency of glyphosate and monoethoxylated alkylamine or aminated alkoxylated alcohol compositions used without pretreatment.

Example 38

The effects of oxalic acid along with aminated alkoxylated alcohols of the formula (9), amino esters of the formula (7), dialkoxylated amines of the formula (39) and amines of the formula (32) on the morning glory plants were evaluated. Table 38a describes the resulting aqueous concentrate compositions containing the glyphosate potassium salt. Glyphosate concentrations were expressed in g ke / liter. Oxalic acid was dissolved, then the glyphosate potassium salt was added, and then the molten surfactant was added. Then the composition was mixed in a batch shaker for 30 minutes at 60 ° C. 24 hours after cooling to room temperature, all samples were stable, transparent and had a yellow color.

Table 38a Composition Glyphosate g / l Component 1 % (w / v) Component 2 % (w / v) 383A2T 62.7 S1 2.0 Oxalic acid 0.2 383B7K 62.7 S1 2.0 - - 383C4D 62.7 S13 2.0 Oxalic acid 0.2 383D3E 62.7 S13 2.0 - - 383E8N 62.7 S5 2.0 Oxalic acid 0.4 383F6V 62.7 S5 2.0 - - 383G7Q 62.7 S18 2.0 Oxalic acid 0.4 383H0O 62.7 S18 2.0 - -

The compositions shown in table 38a, composition 725K, composition 570I and Roundup UltraMax were applied to morning glory plants (IPOSS). The results, average for all replicates of experiments for each treatment, are presented in table 38b.

Table 38b
% IPOSS inhibition 14 days after treatment Composition 200 g ke / ha 400 g ke / ha 600 g ke / ha 800 g ke / ha 383A2T 63.3 80.8 82.5 86.7 383B7K 54,2 79.2 82.5 83.3 383C4D 76.7 84.2 88 90.5 383D3E 60.8 80 82.5 87.5 383E8N 79.2 86.7 87.5 90.5 383F6V 76.7 83.5 85 86.7 383G7Q 78.3 82.5 86.7 85.8 383H0O 45 79.2 80.8 84.2 Composition 725K 6.7 54,2 70 73.3 Composition 570I 17.5 54,2 77.5 79.2 Roundup ultramax 27.5 76.7 80.8 85

All compositions containing oxalic acid had higher efficacy than similar compositions not containing oxalic acid. The ethoxylated cocoamine-2EO surfactant and C _16-18 O (EO) 15-dimethylpropyl surfactants in combination with oxalic acid gave the greatest effectiveness.

Example 39

The effect of oxalic acid on a monoethoxylated alkylamine surfactant in dilute glyphosate potassium salt formulations was evaluated. Aqueous concentrate compositions were prepared containing the glyphosate potassium salt in a concentration expressed in g ke / liter and the additional ingredients shown in table 39a.

Table 39a Composition Glyphosate g / l Component 1 wt.% Component 2 wt.% Component
3 wt.% 026F0A 62 S4 2.0 - - - - 026G4T 62 S4 2.0 Oxalic acid 0.41 - - 026H7J 62 S4 2.0 Oxalic acid 0.21 - - 026I4F 62 S5 2.0 Oxalic acid 0.46 - - 026J3Y 62 S5 2.0 - - - - 026K6X 62 S4 1,0 Oxalic acid 0.33 S5 3.0 026L9O 62 S4 1,0 - - S5 1,0

The compositions presented in table 39a and comparative compositions: composition 725K, composition 570I, Roundup UltraMax and composition 41I, were applied to the plants of Theofrasta Abutilon (Abutilon theophrasti, ABUTH) and millet blackberry (Echinochloa crus-galli var.frumentae, ECHCF). The results, the average of all repetitions of experiments for each treatment, are presented in tables 39b and 39c.

Table 39b
% Inhibition of ABUTH 17 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 026F0A 56.7 78.3 88.3 91.7 026G4T 74,2 85.8 89.2 93.3 026H7J 74,2 90.8 96.2 97.8 026I4F 76.7 83.3 84.2 91.7 026J3Y 28.3 70 79.2 85 026K6X 58.3 87.5 88.3 95 026L9O 32,5 75 82.5 87.5 Composition 725K 0 23.3 60.8 72.5 Composition 570I 0 25 63.3 75.8 Roundup ultramax 16.7 77.5 85.8 89.2 Composition 41I 36.7 78.3 83.3 91.7 Table 39c
% Inhibition of ECHCF 17 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 026F0A 52,5 75 83.3 88 026G4T fifty 58.3 68.3 77.5 026H7J 56.7 74,2 83.3 92.7 026I4F 57.5 75 85 84.2 026J3Y 56.7 74,2 81.7 88.3 026K6X 60.8 79.2 82.5 91 026L9O 58.3 74,2 85 90 Composition 725K 1.7 34.2 49.2 50.8 Composition 570I 2,5 47.5 52,5 55 Roundup ultramax 40.8 66.7 84.2 86.7 Composition 41I 53.3 72.5 80 87

The efficacy of all compositions containing oxalic acid exceeded that of Roundup Ultra and the composition containing glyphosate + S4 potassium salt. The composition containing the potassium salt of glyphosate + S4 + 0.21% oxalic acid in relation to kef glyphosate: oxalic acid, comprising 28: 1, had the greatest efficiency. Compositions containing 0.21% oxalic acid had slightly higher efficacy than compositions containing 0.41% oxalic acid. The addition of oxalic acid led to an increase in the effectiveness of compositions containing the potassium salt of glyphosate and S4 (monoethoxylated alkylamine) than the effectiveness of the composition containing the potassium salt of glyphosate and S5 (Ethomeen C12).

Example 40

The efficacy of monoethoxylated alkylamine surfactants was evaluated along with dipotassium oxalate at various surfactant loads. Table 40a describes the resulting aqueous concentrate compositions containing the glyphosate potassium salt. Glyphosate concentrations are expressed in g ke / liter.

Table 40a Composition Glyphosate g / l Component 1 % (w / v) Component 2 % (w / v) 062A4Y 62 - - - - 062B0C 62 - - Dipotassium oxalate 0.75 062O2T 62 S34 1.37 Dipotassium oxalate 0.75 062P7A 62 S34 1.16 Dipotassium oxalate 0.75 062Q4K 62 S34 1,02 Dipotassium oxalate 0.75 062R1R 62 S35 1.37 Dipotassium oxalate 0.75 062S7M 62 S35 1.16 Dipotassium oxalate 0.75 062T5G 62 S35 1,02 Dipotassium oxalate 0.75

The compositions shown in Table 40a and comparative compositions: composition 725K, composition 570I and Roundup UltraMax, were applied to the plants of Theofrasta Abutilon (Abutilon theophrasti, ABUTH) and millet blackberry (Echinochloa crus-galli var.frumentae, ECHCF). The results, averaged over all replicates of experiments for each treatment, are presented in tables 40b and 40c.

Table 40b
% Inhibition of ABUTH 15 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 062A4Y 0 13.3 64,2 77.5 062B0C 77.5 83.3 89.2 95.5 062O2T 65 87.5 89.2 93.2 062P7A 68.3 85 90 95.7 062Q4K 75.8 83.3 89.3 90.8 062R1R 74,2 85 88.3 91.7 062S7M 75.8 82.5 89.2 90 062T5G 35.8 81.7 89.2 94.7 Composition AMM-GLY2S 0 3.3 20.8 51.7 Roundup ultramax fifteen 75.8 82.5 89.2 Composition AMM-GLY1S 0 37.5 46.7 80 Table 40c
% Inhibition of ECHCF 15 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 062A4Y 13.3 43.3 56.7 61.7 062B0C 46.7 52,5 57.5 58.3 062O2T 57.5 75.8 84.2 89.8 062P7A 55 65 83.3 88.3 062Q4K 57.5 70.8 78.3 84.2 062R1R 55 70.8 83,2 88 062S7M 56.7 70 77.5 85.5 062T5G 52,5 64,2 78.3 86.5 Composition AMM-GLY2S 2,5 31.7 42.5 52,5 Roundup ultramax 59.2 75.8 85.8 93.3 Composition AMM-GLY1S 28.3 55 58.3 70

Reduced loading of surfactants in combination with oxalic acid gave a higher efficacy against Teofrast and cockerel millet than AMM-GLY1S, a higher efficacy against Teofrast rodent than Roundup UltraMax and a slightly lower efficiency against millet millet than Roundup UltraMax. Efficiency was proportional to all tested surfactant batches.

Example 41

The effectiveness of oxalic acid was evaluated together with the short-chain EO-talloamine used as a surfactant in the diluted glyphosate potassium salt composition. Aqueous concentrate compositions were prepared containing glyphosate potassium salt in a concentration expressed in g ke / liter and auxiliary ingredients as indicated in table 41a. All components were added simultaneously, then the composition was mixed in a batch shaker for 30 minutes at 60 ° C. 24 hours after cooling to room temperature, all samples were stable, transparent and had a yellow color with the exception of composition 363B7U, which was unstable and cloudy.

Table 41a Composition Glyphosate g / l Component 1 % (w / v) Component 2 % (w / v) 363A1B 62.7 S12 2.0 - - 363B7U 62.7 - - Oxalic acid 2.0 363C5J 62.7 S12 2.0 Oxalic acid 0.08 363D4Q 62.7 S12 2.0 Oxalic acid 0.1 363E5T 62.7 S12 2.0 Oxalic acid 0.13 363F9K 62.7 S12 2.0 Oxalic acid 0.15 363G6V 62.7 S12 2.0 Oxalic acid 0.2 363H5G 62.7 S12 2.0 Oxalic acid 0.1

The compositions shown in table 41a and comparative compositions: composition 725K, composition 570I, Roundup UltraMax and composition 41I, were applied to the plants of the Theofrasta Abutilon (Abutilon theophrasti, ABUTH). The results, average for all replicates of experiments for each treatment, are presented in table 41b.

Table 41b
% Inhibition of ABUTH Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 363A1B 15.8 73.3 82.5 86.7 363B7U 62.5 80.8 83.3 85 363C5J 65 79.2 86.7 87.5 363D4Q 41.7 80.8 87.5 90 363E5T 54,2 80.8 86.7 90 363F9K 60.8 80.8 87.5 91.7 363G6V 70 85 87.5 92.5 363H5G 41.7 79.2 85 90.8 Composition 725K 0 26.7 63.3 70 Composition 570I 0 43.3 60.8 72.5 Roundup ultramax 40 72.5 85 87.5 Composition 41I 64,2 80 86.7 89.2

Most oxalic acid containing mixtures of Witcamine 405 showed an anti-Theofrast effect equal to Roundup® UltraMax. Oxalic acid at any level of addition gave a slightly greater efficiency compared to the surfactant Witcamine 405.

Example 42

The effect of oxalic acid on the efficacy of ethoxylated cocoamines in dilute glyphosate potassium salt compositions in hard water was evaluated. Table 42a presents aqueous concentrate compositions containing the glyphosate potassium salt. Glyphosate concentrations were expressed in g ke / liter.

Table 42a Composition Glyphosate g / l Component 1 % (w / v) Component 2 % (w / v) 045A2M 62 S5 2.0 - - 045V2E 62 S5 2.0 Oxalic acid 0.3 045C9I 62 S19 2.0 - - 045D0P 62 S19 2.0 Oxalic acid 0.3 045G4H 62 S20 2.0 - - 045H5Y 62 S20 2.0 Oxalic acid 0.3 045I8J 62 - - - - 045J1Z 62 - - Oxalic acid 0.3

The compositions shown in table 42a, and composition 725K, composition 570I, Roundup UltraMax were applied to the plants of Theofrasta Abutilon (Abutilon theophrasti, ABUTH). The results, average for all replicates of experiments for each treatment, are presented in table 42b.

Table 42b
% Inhibition of ABUTH 14 days after treatment Composition 100 g ke / ha 150 g ke / ha 200 g ke / ha 400 g ke / ha 045A2M 0 0 0 75 045B2E 0 5 10 86.7 045C9I 0 0 thirty 80 045D0P 0 10 62.5 87.5 045G4H 0 3.3 16.7 83.3 045H5Y 1.7 5 40.8 87.5 045I8J 13.3 25 38.3 53.3 045J1Z 27.5 26.7 71.7 85 Composition 725K 0 0 0 40 Composition 570I 0 0 0 thirty Roundup ultramax 0 0 5 75

All compositions were diluted with hard water. The addition of oxalic acid gave various increases in efficiency in the following order: C12 (2EO)> C15 (5EO)> C25 (15EO).

Example 43

The effect of oxalic acid on the effectiveness of ethoxylated thalloamines (surfactants) in dilute compositions of glyphosate potassium salt in hard water was evaluated. Table 43a provides aqueous concentrate compositions containing the glyphosate potassium salt. Glyphosate concentrations were expressed in g ke / liter.

Table 43a Composition Glyphosate g / l Component 1 % (w / v) Component 2 % (w / v) 045K3S 62 S5 2.0 - - 045L9O 62 S5 2.0 Oxalic acid 0.3 045M3B 62 S19 2.0 - - 045N5T 62 S19 2.0 Oxalic acid 0.3 045Q4Y 62 S20 2.0 - - 045R6J 62 S20 2.0 Oxalic acid 0.3 045S3L 62 - - - - 045T7G 62 - - Oxalic acid 0.3

The compositions shown in Table 43a, composition 725K, composition 570I, and Roundup UltraMax were applied to the plants of the Theofrasta Abutilon (Abutilon theophrasti, ABUTH). The results, average for all replicates of experiments for each treatment, are presented in table 43b.

Table 43b
% Inhibition of ABUTH 18 days after treatment Composition 100 g ke / ha 150 g ke / ha 200 g ke / ha 400 g ke / ha 045K3S 0 0 16.7 77.5 045L9O 7.5 21.7 34.2 86.3 045M3B 10 23.3 38.3 80 045N5T 15.8 48.3 56.7 90.8 045Q4Y 3.3 twenty 45.8 84.2 045R6J 9.2 38.3 61.7 87.5 045S3L 0 21.7 31.7 63.3 045T7G 10.8 32,5 38.3 82.5 Composition 725K 0 0 0 26.7 Composition 570I 0 0 0 26.7 Roundup ultramax 0 0 25 70

Compositions with oxalic acid were more effective than similar compositions not containing oxalic acid.

Example 44

The effectiveness of oxalic acid was evaluated along with diethoxylated ether-amine surfactants. Table 44a presents diluted aqueous glyphosate potassium salt formulations. Glyphosate concentrations were expressed in g ke / liter. Oxalic acid was dissolved, glyphosate potassium salt and surfactant were added. Then the composition was mixed in a batch shaker for 30 minutes at 60 ° C. 24 hours after cooling to room temperature, all samples were stable, transparent and had a yellow color.

Table 44a Composition Glyphosate g / l Component 1 % (w / v) Component 2 % (w / v) 615A4F 484.4 S36 12.0 - - 615V9K 484.4 S36 12.0 Oxalic acid 1,5 615C7S 62.7 S37 2.0 - - 615D1B 62.5 S37 2.0 Oxalic acid 0.25 615E5I 62.6 S38 2.0 - - 615F5A 62.5 S38 2.0 Oxalic acid 0.25 615G8Y 62.7 S39 2.0 - - 615H5W 62.7 S39 2.0 Oxalic acid 0.25

The compositions shown in table 44a, composition 725K, composition 570I, and Roundup UltraMax were applied to the plants of the Theofrasta abutilus (Abutilon theophrasti, ABUTH). The results, averaged over all replicates of experiments for each treatment, are presented in tables 44b.

Table 44b
% Inhibition of ABUTH 14 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 615A4F 7.5 75.8 90 89.2 615V9K 78.3 88.3 94.2 94.5 615C7S 65 84.2 90 90.8 615D1B 74,2 90 92.5 92.5 615E5I 40 84.2 89.2 90 615F5A 68.3 89.2 92.5 92.5 615G8Y 32,5 75 88.3 90.8 615H5W 65.8 85.8 91.3 92.5 Composition 725K 0 40 78.3 82.5 Composition 570I 8.3 70.8 80 84.2 Roundup ultramax 39.2 81.7 90 92.5

Oxalic acid enhanced the effect of the tested ether-amine surfactants against the Theofrast rodent. This enhancement of the action of surfactants with oxalic acid, taken in relation to kef glyphosate: oxalic acid = 24: 1, was similar for all surfactants, and each of them exceeded the effect of the standard preparation Roundup UltraMax against Theofrasta funicularis.

S36-containing composition without oxalic acid had the weakest efficiency, but with the addition of oxalic acid gave the most powerful effect.

Example 45

The efficacy of oxalic acid and diethoxylated ether-amine surfactants was evaluated. Table 45a describes the resulting aqueous concentrate compositions containing the glyphosate potassium salt. Glyphosate concentrations are expressed in g ke / liter. Oxalic acid was dissolved, glyphosate potassium salt and molten surfactant were added. Then the composition was mixed in a batch shaker for 30 minutes at 60 ° C. 24 hours after cooling to room temperature, all samples were stable, transparent and had a yellow color with the exception of composition 392H8U, which was unstable, cloudy and separated into phases.

Table 45a Composition Glyphosate g / l Component 1 % (w / v) Component 2 % (w / v) 392A0L 484.4 S36 10.0 - - 392B2S 488.1 S36 10.0 Oxalic acid 1,2 392С5T 62.7 S37 1,63 - - 392D2K 62.9 S37 1,63 Oxalic acid 0.2 392E5C 62.5 S38 1,63 - - 392F9V 62.5 S38 1,63 Oxalic acid 0.2 392G1D 488.1 S39 10.0 - - 392H8U 488.1 S39 10.0 Oxalic acid 1,2

The compositions shown in table 45a, composition 725K, composition 570I and Roundup UltraMax were applied to the plants of Theofrasti abutilus (Abutilon theophrasti, ABUTH). The results, average for all replicates of experiments for each treatment, are presented in table 45b.

Table 45b
% Inhibition of ABUTH 14 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 392A0L 52,5 80 88 90.8 392B2S 56.5 85 90.8 92.5 392С5T 68.3 83.3 90 93 392D2K 86.3 91.7 96.3 98.2 392E5C 54,2 80.8 87.5 90.8 392F9V 83 84.2 88.3 90.8 392G1D fifty 80 85.8 89.2 392H8U 86.3 88.3 92.5 96.3 Composition 725K 0 19.2 60.8 70.8 Composition 570I 10 51.7 78.3 82.5 Roundup ultramax fifty 82.5 90.8 92.5

Ether-amine compositions containing oxalic acid had higher efficacy than similar compositions without oxalic acid, and their efficacy exceeded that of the standard preparation Roundup UltraMax. PEG showed highest efficiency (2) -iso-C ₁₃ -efiropropilamin together with oxalic acid.

Example 46

The efficacy of silicone surfactants having amine and phosphate head groups with or without oxalic acid in diluted glyphosate potassium salt formulations was evaluated. Table 46a describes the resulting aqueous concentrate compositions containing the glyphosate potassium salt. Glyphosate concentrations are expressed in g ke / liter. Oxalic acid was dissolved, and then the surfactant and glyphosate potassium salt were added. After that, the composition was mixed in a batch shaker for 30 minutes at 60 ° C. 24 hours after cooling to room temperature, the compositions 627A6B, 629B9F and 627F1Z were stable, transparent and had a yellow color. All other drugs were unstable and cloudy.

Table 46a Composition Glyphosate g / l Component 1 % (w / v) Component 2 % (w / v) 627A6B 62.7 S25 2.0 - - 627B9F 62.7 S26 2.0 - - 627C4J 62.7 S27 2.0 - - 627D4J 62.7 S28 2.0 - - 627E5U 62.7 S29 2.0 - - 627F1Z 62.7 S25 2.0 Oxalic acid 0.3 627G0P 62.7 S28 2.0 Oxalic acid 0.3

The compositions shown in table 46a and comparative compositions: composition 725K, composition 570I and Roundup UltraMax, were applied to the plants of Theofrasta Abutilon (Abutilon theophrasti, ABUTH), millet blackberry (Echinochloa crus-galli var.frumentae, ECHCF) and Ipomoea (IPCH ) The results, the average of all repetitions of experiments for each treatment, are presented in tables 46b, 46c and 46d.

Table 46b
% Inhibition of ABUTH 14 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 627A6B 79.2 84.2 90.8 95.2 627B9F 75.8 84.2 92.5 95.2 627C4J 73.3 77.5 88.3 88.3 627D4J 70.8 72.5 86.7 85.8 627E5U 79.2 80.8 87.5 90 627F1Z 80.8 83.3 92.3 93.3 627G0P 80 85.8 87.5 88.3 Composition 725K thirty 60 81.7 83.3 Composition 570I 61.7 70 83.3 85 Roundup ultramax 74,2 85.8 91.8 95.5 Table 46c
% Inhibition of ECHCF 14 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 627A6B 60 70.8 80.8 94.3 627B9F 57.5 66.7 86.7 93 627C4J 55 65.8 85 87.5 627D4J 55 60.8 76.7 80 627E5U 56.7 64,2 75 77.5 627F1Z 59.2 69.2 85.8 89.8 627G0P 57.5 64,2 73.3 76.7 Composition 725K 47.5 59.2 64,2 65 Composition 570I 47.5 60 61.7 63.3 Roundup ultramax 65 75.8 93.5 98.2 Table 46d
% IPOSS inhibition 14 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 627A6B 78.3 85.8 85.8 85.8 627B9F 77.5 82.5 85 85.8 627C4J 76.7 80.8 82.5 83.3 627D4J 77.5 84.2 84.2 85 627E5U 78.3 84.2 85 87.5 627F1Z 82.5 82.5 85 87.5 627G0P 78.3 82.5 84.2 85 Composition 725K 70 82.5 84.2 85 Composition 570I 70.8 83.3 84.2 85.8 Roundup ultramax 78.3 84.2 85.8 86.7

The compositions of Lambent Phos A-100 + oxalic acid, Lambent Phos A-100 and Lambent Phos A-150 had an efficiency equal to that of Roundup UltraMax against Theofrast and morning glory. The presence of oxalic acid increased the effectiveness of the amine surfactant Lambent PD, but gave an increase in efficiency compared to the surfactant Lambent Phos A, taken separately.

Example 47

The efficacy of oxalic acid and the alkylamine surfactant Ethomeen C12, present in various proportions in dilute glyphosate potassium salt formulations, was evaluated. Table 47a describes the resulting aqueous concentrate compositions containing the glyphosate potassium salt. Glyphosate concentrations are expressed in g ke / liter. Oxalic acid was dissolved, a molten surfactant was added, and then the glyphosate potassium salt was added. After that, the composition was mixed in a batch shaker for 30 minutes at 60 ° C. 24 hours after cooling to room temperature, all samples were stable, transparent and colorless with the exception of composition 621B4L, which was unstable and formed a precipitate.

Table 47a Composition Glyphosate g / l Component 1 % (w / v) Component 2 % (w / v) 621A0V 62.7 S5 2.0 - - 621B4L 62.7 - - Oxalic acid 2.0 621С3Е 62.7 S5 1.9 Oxalic acid 0.1 621D8H 62.7 S5 1.8 Oxalic acid 0.2 621E7S 62.7 S5 1,6 Oxalic acid 0.4 621F3X 62.7 S5 1.4 Oxalic acid 0.6 621G9K 62.7 S5 1,2 Oxalic acid 0.8 621N2A 62.7 S5 2.0 Oxalic acid 2.0

The compositions shown in table 47a, composition 725K, composition 570I, and Roundup UltraMax were applied to the plants of the Theofrasta Abutilon (Abutilon theophrasti, ABUTH). The results, average for all replicates of experiments for each treatment, are presented in table 47b.

Table 47b
% Inhibition of ABUTH 14 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 621A0V fifteen 51.7 78.3 83.3 621B4L 36.7 60.8 72.5 84.2 621С3Е 48.3 72.5 82.5 88.3 621D8H 60.8 75 86.7 85 621E7S 59.2 74,2 80.8 88.3 621F3X 37.5 73.3 78.3 85 621G9K 75 80 83.3 86.7 621N2A 51.7 78.3 82.5 87.5 Composition 725K 0 1.7 46.7 60 Composition 570I 0.8 24.2 60.8 73.3 Roundup ultramax 35 55 80 85

Oxalic acid at any concentration gave a slight increase in efficiency compared to just one Ethomeen C12 surfactant system. An increase in the concentration of oxalic acid and a simultaneous decrease in the concentration of the surfactant Ethomeen C12 led to a slight decrease in efficiency. The ratio of kef glyphosate: oxalic acid, comprising 3: 1, without a surfactant gave an efficiency similar to that of Roundup UltraMax.

Example 48

The effectiveness of oxalic acid was evaluated along with a nonionic and anionic surfactant in dilute glyphosate potassium salt formulations. Table 48a describes the resulting aqueous concentrate compositions containing the glyphosate potassium salt. Glyphosate concentrations are expressed in g ke / liter. Oxalic acid was dissolved, glyphosate potassium salt and surfactant were added. After that, the composition was mixed in a batch shaker for 30 minutes at 60 ° C. 24 hours after cooling to room temperature, all samples were stable and transparent.

Table 48a Composition Glyphosate g / l Component 1 % (w / v) Component 2 % (w / v) 613A5B 62.7 S31 2.0 - - 613B9I 62.8 S31 2.0 Oxalic acid 0.25 613C5G 62.8 S31 2.0 Oxalic acid 0.5 613D0K 62.9 S32 2.0 - - 613E7B 62.9 S32 2.0 Oxalic acid 0.25 613F7S 63 S32 2.0 Oxalic acid 0.5 613G3Z 62.8 S33 2.0 - - 613H8J 62.9 S33 2.0 Oxalic acid 0.5

The compositions shown in table 48a, composition 725K, composition 570I, and Roundup UltraMax were applied to the plants of the Theofrasta Abutilon (Abutilon theophrasti, ABUTH) and hemp seed (SEBEX). The results, averaged over all replicates of experiments for each treatment, are presented in tables 48b and 48c.

Table 48b
% Inhibition of ABUTH 14 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 613A5B fifteen 67.5 80 84.2 613B9I 45 85.8 90.8 92.5 613C5G 64,2 85 90 90 613D0K 22.5 76.7 80 85.8 613E7B 58.3 78.3 85.8 90 613F7S 65 80.8 87.5 90.8 613G3Z 22.5 62.5 70.8 78.3 613H8J 53.3 75.8 80 86.7 Composition 725K 0 47.5 70 79.2 Composition 570I 10.8 55 74,2 81.7 Roundup ultramax 30.8 78.3 88.3 90

Oxalic acid in combination with any of the surfactants provided an increase in efficiency to a level exceeding the effectiveness of the standard preparation Roundup UltraMax.

Table 48c
% Inhibition of SEBEX 18 days after treatment Composition 200 g ke / ha 300 g ke / ha 400 g ke / ha 600 g ke / ha 613A5B 60.8 70 75.8 79.2 613B9I 47.5 63.3 76.7 80 613C5G 57.5 59.2 70.8 79.2 613D0K 41.7 68.3 75 75 613E7B 30.8 57.5 66.7 75 613F7S 20.8 58.3 63.3 75 613G3Z 24.2 48.3 57.5 74,2 613H8J 23.3 43.3 50.8 72.5 Composition 725K 0 0 0 2,5 Composition 570I 0 0 0 6.7 Roundup ultramax 40 56.7 74,2 80

Despite the presence of oxalic acid, the level of herbicidal activity against hemp production was similar to that of standard preparations.

Example 49

The effectiveness of oxalic acid was evaluated together with a nonionic alkyl glycoside and anionic ethoxylated phosphoric acid ester used as surfactants. Table 49a describes the resulting aqueous concentrate compositions containing the glyphosate potassium salt. Glyphosate concentrations are expressed in g ke / liter. Oxalic acid was dissolved and then glyphosate potassium salt and surfactants were added. After that, the composition was mixed in a batch shaker for 30 minutes at 60 ° C. 24 hours after cooling to room temperature, all samples were stable, transparent and had a yellow color.

Table 49a Composition Glyphosate g / l Component 1 % (w / v) Component 2 % (w / v) 394A7B 62.7 S32 2.0 - - 394B7U 62.7 S32 2.0 Oxalic acid 0.3 394C2Z 62.7 S47 2.0 - - 394D0K 62.7 S47 2.0 Oxalic acid 0.3 394E6Y 62.7 S48 2.0 - - 394F3X 62.7 S48 2.0 Oxalic acid 0.3 394G4J 62.7 S33 2.0 - - 394H2I 62.7 S33 2.0 Oxalic acid 0.3

The compositions shown in table 49a, composition 725K, composition 570I and Roundup UltraMax were applied to the plants of Theofrasta Abutilon (Abutil theophrasti, ABUTH). The results, the average of all replicates of experiments for each treatment, are presented in table 49b.

Table 49b
% Inhibition of ABUTH 15 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 394A7B 61.7 64,2 80 82.5 394B7U 65.8 74,2 86.7 87.5 394C2Z 65.8 72.5 80.8 83.3 394D0K 50.8 74,2 85 85.8 394E6Y 67.5 75 86.7 87.5 394F3X 75.8 81.7 87.5 88.3 394G4J 61.7 70 75 81.7 394H2I 67.5 71.7 84.2 85 Composition 725K 1.7 49.2 75 77.5 Composition 570I 22.5 46.7 79.2 80.8 Roundup ultramax fifty 77.5 88.8 90

Mixtures of oxalic acid gave an increase in the effectiveness of the anti-Tibetan Theofrast at the tested ratios of kef glyphosate: oxalic acid, constituting 3: 1 and 20: 1, respectively.

Example 50

The efficacy of oxalic acid and its organic salt with cationic ether-amine surfactants in the glyphosate potassium salt compositions was evaluated. Table 50a describes the resulting aqueous concentrate compositions containing the glyphosate potassium salt. Glyphosate concentrations are expressed in g ke / liter. The bases were added to water, oxalic acid was dissolved in it, and then the molten surfactant and potassium salt of glyphosate were added. After that, the composition was mixed in a batch shaker for 30 minutes at 60 ° C. 24 hours after cooling to room temperature, all samples were stable, transparent and colorless.

Table 50a Composition Glyphosate g / l Component 1 % (wt./wt.) Component 2 % (wt./wt.) Component 3 % (w / v) 638A2B 62.7 S30 2 - - - - 638B9K 62.7 S30 2 Oxalic acid 0.3 - - 638C4J 62.7 S30 2 Oxalic acid 0.26 S59 0.5 638D1L 62.7 S30 2 Oxalic acid 0.26 S53 0.5 638E3C 62.7 S30 2 Oxalic acid 0.26 S68 0.5 638F7N 62.7 S30 1.9 Oxalic acid 0.15 - - 638G5B 62.7 S30 1,6 Oxalic acid 0.4 - -

The compositions shown in Table 50a, composition 725K, composition 570I, and Roundup UltraMax were applied to the plants of the Theofrasta Abutilon (Abutilon theophrasti, ABUTH). The results, average for all replicates of experiments for each treatment, are presented in table 50b.

Table 50b
% Inhibition of ABUTH 14 days after treatment Composition 200 g ke / ha 300 g ke / ha 400 g ke / ha 600 g ke / ha 638A2B 70 85.8 93.2 96.8 638B9K 72.5 86.7 92.7 96.3 638C4J 79.2 90 91.2 97.8 638D1L 80 89.7 96.5 98.5 638E3C 74,2 83.3 90.2 93.3 638F7N 67.5 80.8 86.7 95.2 638G5B 63.3 77.5 82.5 94 Composition 725K 25.8 54,2 69.2 80.8 Composition 570I 39.2 63.3 73.3 83.3 Roundup ultramax 59.2 75 88.3 94.7

Mixtures of oxalic acid enhanced the effect against the teatrope Theofrast compared with the standard preparation UltraMax.

Example 51

The effect of oxalic acid on efficiency was evaluated depending on the EO chain length in compositions with a high loading of glyphosate potassium salt. Aqueous concentrate compositions were prepared containing the glyphosate potassium salt in a concentration expressed in g ke / liter and additional ingredients as indicated in Table 51a.

Table 51a Composition Glyphosate g / l Component 1 g / l Component 2 g / l Component 3 g / l 024A1V 485 S2 131 S5 65 - - 024B7N 485 S3 91 S5 91 - - 024C7B 485 S3 65 S5 65 S2 65 024D3K 485 S3 78 S5 52 S2 65 024E4J 485 S3 91 S5 91 Oxalic acid 13 015A0P 391 S4 131 - - - -

The compositions shown in table 51a and comparative compositions: composition 725K, composition 570I, Roundup UltraMax and composition 41I, were applied to the plants of the Theofrasta Abutilon (Abutilon theophrasti, ABUTH) and the millet blackberry (Echinochloa crus-galli var.frumentae, ECHCF). The results, average for all replicates of experiments for each treatment, are presented in tables 51b and 51c.

Table 51b
% Inhibition of ABUTH 15 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 024A1V 15.8 76.7 83.3 84.2 024B7N 40 80.8 86.7 88.3 024C7B 0 0 1.7 1.7 024D3K 29.2 80.8 82.5 90 024E4J 75 82.5 91.7 92.5 015A0P 55 80 86.7 89.2 Composition 725K 0 fifteen 73.3 75.8 Composition 570I 0.8 twenty 71.7 80.8 Roundup ultramax 45.8 80.8 87.5 90 Composition 41I 33.3 81.7 87.5 90.8 Table 51c
% Inhibition of ECHCF 15 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 024A1V 35 51.7 65 72.5 024B7N 46.7 53.3 62.5 69.2 024C7B 0 0 1.7 1.7 024D3K 38.3 55.8 70 77.5 024E4J fifty 55 75.8 79.2 015A0P 48.3 54,2 59.2 68.3 Composition 725K 1.7 twenty 45 47.5 Composition 570I 1.7 40 fifty 53.3 Roundup ultramax 21.7 54,2 65 73.3 Composition 41I 39.2 56.7 68.3 72.5

Composition 024E4J, containing oxalic acid together with monoethoxylated alkylamine (11EO) and Ethomeen C12, showed the best herbicidal efficacy against ABUTH and ECHCF. Other compositions had efficacy similar to that of standard glyphosate formulations. Composition 024C7B was atypical, becoming cloudy after dilution in water and showed a small level of herbicidal activity.

Example 52

The effect of oxalic acid on the effectiveness of monoethoxylated amine surfactants with different EO lengths in compositions with a high loading of glyphosate potassium salt was evaluated. Aqueous concentrate compositions were prepared containing the glyphosate potassium salt at a concentration expressed in g ke / liter and additional ingredients as indicated in table 52a.

Table 52a Composition Glyphosate g / l Component 1 g / l Component 2 G / l Component 3 g / l 023A6G 485 S8 105 S4 92 - - 023B6U 486 S8 118 S4 92 - - 023С0Р 487 S9 92 S4 92 - - 023D4R 489 S9 92 S4 92 Oxalic acid 13,2 023E6S 480 S9 104 S4 91 - - 023F6Y 391 S4 121 - - Oxalic acid 7.3 015Y7N 391 S4 121 - - - -

The compositions shown in table 52a and comparative compositions: composition 725K, composition 5701, Roundup UltraMax and composition 411, were applied to the plants of Theofrasta Abutilon (Abutilon theophrasti, ABUTH) and millet blackberry (Echinochloa crus-galli var.frumentae, ECHCF). The results, averaged over all replicates of experiments for each treatment, are presented in tables 52b and 52c.

Table 52b
% Inhibition of ABUTH 14 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 023A6G 21.7 56.7 76.7 84.2 023B6U 25.8 63.3 77.5 83.3 023C0P 14.2 54,2 76.7 81.7 023D4R 36.7 61.7 80.8 87.5 023E6C 34.2 50.8 76.7 80.8 023F6Y 45.8 71.7 88.3 88.3 015Y7N 34.2 68.3 82.5 86.7 Composition 725K 1.7 twenty 52,5 60.8 Composition 570I 3.3 24.2 52,5 58.3 Roundup ultramax 10 60 77.5 86.7 Composition 41I 20.8 60 76.7 86.7 Table 52c
% Inhibition of ECHCF 14 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 023A6G fifty 68.3 75.8 81.7 023B6U 42.5 67.5 75 88.3 023C0P 39.2 70 73.3 83.3 023D4R 41.7 69.2 75 80.8 023E6C 51.7 67.5 73.3 80.8 023F6Y 46.7 67.5 69.2 79.2 015Y7N 51.7 66.7 69.2 80 Composition 725K 2,5 11.7 27.5 37.5 Composition 570I 6.7 16.7 43.3 fifty Roundup ultramax 42.5 61.7 43.3 fifty Composition 41I fifty 69.2 77.5 84.2

Due to an error in the test, compositions 023F6Y and 015Y7N were applied in excess of 10%. This test indicated no differences in efficacy between compositions containing monoethoxylated alkylamine surfactants with 9.5 EO and 11 EO.

Example 53

The effect of oxalic acid was evaluated together with a mixture of surfactants in compositions with a high loading of glyphosate potassium salt. Received aqueous concentrate compositions containing the potassium salt of glyphosate. Glyphosate concentrations are expressed in g ke / liter.

Table 53a Composition Glyphosate g / l Component 1 wt.% Component 2 wt.% Component 3 wt.% 388A6B 487 S21 12.0 - - - - 388B5N 490 S21 10.0 Oxalic acid 1,2 Koh 1,0 388C5T 486 S21 10.0 S22 2.0 - - 388D9J 544 S21 13.0 - - - - 388E0A 548 S21 10.0 Oxalic acid 1,0 Koh 0.45 Composition 470K 472 S23 9.0 S22 4.0 S24 1,0 Composition 390K 391 S4 10.0 - - - -

The compositions shown in table 53a, and comparative compositions: composition 725K, composition 570I and Roundup UltraMax, were applied to the plants of Theofrasta Abutilon (Abutilon theophrasti, ABUTH). The results, average for all replicates of experiments for each treatment, are presented in table 53b.

Table 53b
% Inhibition of ABUTH 16 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 388A6 V 0 5.8 54,2 79.2 388B5N 2,5 60 83.3 90 388С5Т 0 13.3 70.8 81.7 388D9J 0 4.2 56.7 74,2 388EOA 0 32,5 78.3 85 Composition 470K 0 45 80 85 Composition 390K 11.7 76.7 87.5 89.2 Composition 725K 0 0 0.8 8.3 Composition 570I 0 0 33.3 54,2 Roundup ultramax 1.7 77.5 85 90

Compositions 390K and a mixture of coco-2EO-quat and branched PEG 7 C12 alcohol in combination with oxalic acid and KOH were most effective.

Example 54

The efficacy of aminated alkoxylated alcohols of formula (9), dialkoxylated amines of formula (39) and alkoxylated alcohols of formula (49) with a high degree of loading in commercially available standard compositions was evaluated. Aqueous concentrate compositions were prepared containing the glyphosate potassium salt. Glyphosate concentrations are expressed in g ke / liter. Oxalic acid was dissolved, KOH and molten surfactant were added, followed by glyphosate potassium salt. After that, the composition was mixed in a batch shaker for 30 minutes at 60 ° C. 24 hours after cooling to room temperature, all samples were stable.

Table 54a Composition Glyphosate g / l Component 1 wt.% Component 2 wt.% Component 3 wt.% 607A8N 484.4 S40 6.0 S5 6.0 - - 607B3E 480.8 S1 6.0 S5 6.0 - - 607C0R 480.8 S30 6.0 S5 6.0 Oxalic acid 1,2 697D2C 488.1 S19 6.0 S5 6.0 - - 607E5G 488.1 S19 6.0 S5 6.0 Oxalic acid 1,2 607F4K 484.4 S45 6.0 S5 6.0 - - 607G4W 488.1 S45 6.0 S5 6.0 Oxalic acid 1,2 Composition 470K 472 S42 4.0 S43 9.0 Armeen c 1,0

Compositions 607C0R, 607E5G and 607G4W additionally contained 0.7% w / v KOH.

The compositions shown in table 54a and comparative compositions: composition 725K, composition 570I and Roundup UltraMax, were applied to the plants of the Theophrastus abutilus (Abutilon theophrasti, ABUTH). The results, average for all replicates of experiments for each treatment, are presented in table 54b.

Table 54b
% Inhibition of ABUTH 14 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 607A8N 76.7 83.3 96.2 97.5 607B3E 55.8 80 90 95.5 607C0R 76.7 87.5 97.5 97.8 607D2C thirty 79.2 87.5 94.3 607E5G 82.5 85.8 98.8 97.2 607F4K 64,2 80.8 90 94.2 607G4W 85.8 89.2 94.7 99 Composition 470K 25.8 78.3 90 91.7 Composition 725K 11.7 31.7 75.8 77.5 Roundup ultramax 62.5 83.3 90 96.5

The four high-loading 607G4W, 607E5G, 607C0R and 607A8N compositions had higher efficacy than the standard Roundup UltraMax and 470K. Oxalic acid has been shown to increase efficacy against Theophrastus tumeric.

Example 55

The effect of adding oxalic acid was evaluated in terms of attenuating the effects of surfactants compared to commercially available standard preparations. Aqueous concentrate compositions were prepared containing the glyphosate potassium salt. Glyphosate concentrations are expressed in g ke / liter. Oxalic acid was dissolved, then the glyphosate potassium salt and surfactant were added. After that, the composition was mixed in a batch shaker for 30 minutes at 60 ° C. 24 hours after cooling to room temperature, all samples were stable, transparent and had a yellow color.

Table 55a Composition Glyphosate g / l Component 1 wt.% Component 2 wt.% Component 3 wt.% 603A8U 489.1 S21 10.0 Oxalic acid 1,2 - - 603B4Z 492.8 S21 10.0 Oxalic acid 1,2 Koh 1,2 603C8J 496.4 S21 10.0 Oxalic acid 1,2 Koh 1,2 603D2F 489.1 S21 10.0 Oxalic acid 1,6 - - 603E5B 496.4 S21 10.0 Oxalic acid 1,6 Koh 1,2 603F1E 491.8 S5 10.0 Oxalic acid 2,5 - - 603G7K 536 S5 7.0 Oxalic acid 2.0 - - Composition 470K 472 S42 4.0 S23 9.0 S24 1,0

The compositions shown in table 55a, and comparative compositions: composition 725K, composition 570I and Roundup UltraMax, were applied to the plants of Theofrasta Abutilon (Abutilon theophrasti, ABUTH). The results, average for all replicates of experiments for each treatment, are presented in table 55b.

Table 55b
% Inhibition of ABUTH 14 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 603A8U 78.3 85.8 90 94 603B4Z 75 83.3 90 94.8 603C8J 80 87.5 87.5 98.5 603D2F 45.8 82.5 89.2 93.2 603E5B 42.5 84.2 89.2 90 603F1E 70 84.2 86.7 90 603G7K 80 80.8 85 93.3 Composition 470K 66.7 80 85 90 Composition 725K 0 43.3 71.7 78.3 Composition 570I 11.7 56.7 76.7 78.3 Roundup ultramax 70 82.5 90 94.7

The efficacy of cocoquat 2EO + PEG 7 with added oxalic acid against the Teofrast rodent was similar to that of the standard preparation Roundup UltraMax and composition 470K.

Example 56

The effect of hard water on various glyphosate compositions containing either a cationogenic surfactant or a mixture of cationogenic and anionic surfactants with and without oxalic acid was evaluated. Diluted aqueous compositions were prepared containing the glyphosate potassium salt and deionized water. Glyphosate concentrations are expressed in g ke / liter. Mass ratio of ke glyphosate: surfactant was about 3: 1, the mass ratio of kef glyphosate: oxalic acid was about 30: 1. Calcium chloride (500 ppm) was added to some compositions to produce hard water. All components were added simultaneously, and the composition was mixed in a batch shaker for 30 minutes at 60 ° C. 24 hours after cooling to room temperature, all samples were stable, transparent and colorless with the exception of compositions 374D5T and 374H1E, which were unstable and turbid.

Table 56a Composition Glyphosate g / l Component 1 wt.% Component 2 wt.% Component 3 wt.% 374A2B 62.7 S1 2.0 - - - - 374B2E 62.7 S1 2.0 - - CaCl ₂ 0.05 374C8P 62.7 S1 2.0 Oxalic acid 0.2 - - 374D5T 62.7 S1 2.0 Oxalic acid 0.2 CaCl ₂ 0.05 374E3V 62.7 S15 2,5 - - - - 374F4R 62.7 S15 2,5 - - CaCl ₂ 0.05 374G7L 62.7 S15 2,5 Oxalic acid 0.2 - - 374H1E 62.7 S15 2,5 Oxalic acid 0.2 CaCl ₂ 0.05

The compositions shown in table 56a and comparative compositions: composition 725K, composition 725K obtained using hard water (composition 725KN), Roundup UltraMax and Roundup UltraMax obtained using hard water (Roundup UltraMax H), were applied to the plants of Theofrast Abutilon theophrasti, ABUTH). The results, the average of all repetitions of experiments for each treatment, are presented in table 56b.

Table 56b
% Inhibition of ABUTH 18 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 374A2B 28.3 79.2 86.7 89.2 374B2E 0 48.3 81.7 85.8 374C8P 60.8 85 90.8 97 374D5T 0 66.7 85.8 87.5 374E3V 0 56.7 76.7 82.5 374F4R 0 8.3 48.3 70.8 374G7L 43.3 83.3 87.5 92.2 374H1E 10.8 36.7 75 84.2 Composition 725K 0 0 2,5 24.2 Composition 725K H 0 0 0 0 Roundup ultramax 0 53.3 76.7 85 Roundup UltraMax H 0 0 17.5 68.3

The predominant efficacy of oxalic acid was still observed when using hard water obtained by adding 500 ppm CaCl ₂ as a carrier. However, hard water adversely affected efficiency compared to similar formulations prepared using deionized water. But this effect was expected, since oxalic acid should form a chelate complex with calcium present in hard water, and thereby reduce the amount of oxalic acid present, which affects the effectiveness of these compositions. C _14-15 alkyl (EO) 13-dimethylpropylamine surfactants in combination with oxalic acid gave higher efficacy than similarly prepared compositions containing cationic tallowamine / phosphoric ester.

Example 57

The effect of hard water on various glyphosate compositions containing a cationic surfactant with or without oxalic acid was evaluated. Diluted aqueous compositions were prepared containing the glyphosate potassium salt and deionized water. Glyphosate concentrations are expressed in g ke / liter. The mass ratio of kef glyphosate: n surfactant was about 3: 1, and the mass ratio of kef glyphosate: oxalic acid was about 15: 1 or about 18: 1. Calcium chloride (500 ppm) was added to some compositions to produce hard water.

Table 57a Composition Glyphosate g / l Component 1 wt.% Component 2 wt.% Component 3 wt.% 026F5M 62 S4 2.0 - - - - 026G5L 62 S4 2.0 Oxalic acid 0.41 - - 026K7B 62 S4 1,0 Oxalic acid 0.33 S5 1,0 026L3E 62 S4 1,0 - - S5 1,0

The compositions presented in table 57a; the compositions shown in table 57a, to which 500 ppm CaCl ₂ were added (indicated with the addition of the letter “-H”), comparative compositions: composition 725K; composition 725K, obtained using hard water (composition 725K N), was applied to the plants of the teardrop Theofrast (Abutilon theophrasti, ABUTH). The results, the average of all repetitions of experiments for each treatment, are presented in tables 57b.

Table 57b
% Inhibition of ABUTH 17 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 026F5M 46.7 71.7 80.8 93.3 026F5M-H 5 54,2 65 85.8 026G5L 74,2 85 90 95.5 026G5L-H 21.7 71.7 81.7 90 026K7B 62.5 80.8 87.5 93.8 026K7B-H 21.7 52,5 75 85 026L3E 27.5 65 75 92.5 026L3E-H 24.2 35.8 64,2 83.3 Roundup ultramax 46.7 77.5 86.7 91.7 Roundup UltraMax H 0 28.3 60 85

Hard water reduced the effectiveness of all compositions. However, this effect was expected, since oxalic acid should form a chelate complex with calcium present in hard water, and thereby reduce the amount of oxalic acid present, which affects the effectiveness of these compositions. Oxalic acid taken in the relationship of kef glyphosate: oxalic acid, constituting 15: 1 and 18: 1, contributed to an increase in efficiency in both deionized and hard water.

Example 58

We evaluated the effect of oxalic acid included in composition 480I, composition 725K, and TD IQ on the efficacy of these compositions against morning glory plants (IPOSS) and white marie (CHEAL) at different application rates and ratios of the active ingredient to oxalic acid. Each of the compositions 480I, Roundup UltraMax and TD IQ, not containing oxalic acid and containing oxalic acid in a mass ratio of kephonoglyphosate: oxalic acid, constituting 3: 1, 15: 1 and 30: 1, was tested at an application rate of 390, 585, 780 and 1040 g of active ingredient (ke) per hectare. Roundup UltraMax comparative compositions without the addition of oxalic acid were tested for efficacy against IPOSS and CHEAL at application rates of 390, 585, 780, and 1040 g of active ingredient (ke). The results are presented in tables 58 a, b, c and d.

Table 58a
% weed control 22 days after treatment with 480I and oxalic acid Application rate (g ke / ha) g active substance: g oxalic acid % destruction IPOSS % destruction CHEAL 390 - 41.5 83.8 390 3: 1 52 75,5 390 15: 1 59 78.8 390 30: 1 50,5 73.5 585 - 82.5 92 585 3: 1 83 85.5 585 15: 1 82.3 91.5 585 30: 1 82.3 91.5 780 - 89 89.3 780 3: 1 86 88 780 15: 1 92.3 90.3 780 30: 1 83.5 90.3 1040 - 92.3 92 1040 3: 1 89.8 90 1040 15: 1 83.8 90 1040 30: 1 88.3 91 Table 58b
% weed control 22 days after treatment with 725K and oxalic acid Application rate (g ke / ha) g active substance: g oxalic acid % destruction IPOSS % destruction CHEAL 390 - 46 31.8 390 3: 1 45.3 27.5 390 15: 1 45 21.3 390 30: 1 51.5 36.3 585 - 61.5 41.3 585 3: 1 66.8 36.3 585 15: 1 69 31.3 585 30: 1 69 33 780 - 87.8 38 780 3: 1 70.8 31.3 780 15: 1 83.8 41.3 780 30: 1 84 36.3 1040 - 93.3 41.5 1040 3: 1 84 48.8 1040 15: 1 82.3 41.8 1040 30: 1 78.8 43.8

Table 58c
% weed control 22 days after treatment with TD IQ and oxalic acid Application rate (g ke / ha) g active substance: g oxalic acid % destruction IPOSS % destruction CHEAL 390 - 48.8 76 390 3: 1 52.8 77.5 390 15: 1 52 80.5 390 30: 1 52,5 83.5 585 - 74.3 87.3 585 3: 1 79.5 90.5 585 15: 1 84 88.8 585 30: 1 76.3 89 780 - 88.3 88.5 780 3: 1 86.8 93.3 780 15: 1 95.3 87.5 780 30: 1 92.5 91.5 1040 - 85 87.5 1040 3: 1 94.5 89.5 1040 15: 1 86 84 1040 30: 1 88.8 90.3 Table 58d
% weed control 22 days after treatment with Roundup UltraMax without the addition of oxalic acid Application rate
(g ke / ha) % destruction IPOSS % destruction CHEAL 390 50.3 82.5 585 79.8 92 780 91.5 88.5 1040 90.3 84

TD IQ compositions comprising oxalic acid generally showed significantly higher efficacy against IPOSS and CHEAL than TD IQ.

The 480I compositions comprising oxalic acid had significantly higher anti-IPOSS efficacy than the 480I composition or similar.

Example 59

The effect of oxalic acid included in composition 360I, composition 450IS and composition 450I on the efficacy of these compositions against morning glory plants (IPOSS) was evaluated at various application rates and ratios of the active ingredient to oxalic acid. Each of the compositions: composition 360I, composition 450IS and composition 450I, prepared without oxalic acid, in mass ratios ke glyphosate: oxalic acid, constituting 3: 1, 15: 1 and 30: 1, was tested at a rate of application of the active ingredient of 390, 585, 780 and 1040 g of active ingredient (ke) per hectare. Comparative Compositions Roundup UltraMax Dry without the addition of oxalic acid was tested for efficacy against IPOSS at a rate of application of the active ingredient of 390, 585, 780 and 1040 g of active ingredient (ke) per hectare. The results are presented in table 59a.

Table 59a
% destruction of IPOSS 21 days after treatment with 360I, 450IS, 450I and Roundup UltraMax Dry Application rate
(g ke / ha) Glyphosate: SCH Composition 360I Composition 450IS Composition 450I Roundup UltraMax Dry 390 - 50,5 51 47.5 46.8 390 3: 1 48 44 42.5 - 390 15: 1 49.8 45.3 49.8 - 390 30: 1 53.8 49.3 44.3 - 585 - 62.3 63.8 62 66.3 585 3: 1 65.5 59 62 - 585 15: 1 63.8 63 62 - 585 30: 1 63.5 66 65.8 - 780 - 76.5 81.5 77.5 75.8 780 3: 1 73.3 77.8 70.8 - 780 15: 1 68.8 72 74 - 780 30: 1 78.5 79.3 74.3 - 1040 - 83.3 90.7 79.8 90.3 1040 3: 1 79.8 77.5 77.8 - 1040 15: 1 88 77.8 72 - 1040 30: 1 78.5 80.8 78.3 -

In general, the efficacy of compositions containing oxalic acid when treated with IPOSS did not differ significantly from the efficacy of compositions containing no oxalic acid.

Example 60

The effect of oxalic acid, included in the 360I composition, the 450IS composition and the 450I composition, on the effectiveness of these compositions against plants of Ipomoea angustifolia (IPOLA), Theofrastus theutra (ABUTH), Astragalus crescent (CASOB) and hemp hemp (SEBEX) was evaluated at various application rates and glyphosate to oxalic acid ratios. Each of the compositions: composition 360I, composition 450IS, and composition 450I, prepared without oxalic acid, with a mass ratio of kef glyphosate: oxalic acid, constituting 3: 1, 15: 1 and 30: 1, was tested at a rate of application of the active ingredient 325 , 520, 715 and 910 g of active substance (ke) per hectare. Comparative Roundup UltraMax Dry formulations without the addition of oxalic acid were tested for efficacy against IPOLA, ABUTH, CASOB and SEBEX at rates of application of the active ingredient 325, 520, 715 and 910 g (ke) per hectare. The results, expressed as% destruction, are presented in tables 60 a, b, c and d.

Table 60a
% weed control 24 days after treatment with 360I and oxalic acid Application rate (g ke / ha) g ke: g oxalic acid IPOLA Abuth Casob SEBEX 325 - fifty 52,5 76.3 43.8 325 3: 1 62.5 63.8 76.3 47.5 325 15: 1 60 58.8 80 52,5 325 30: 1 62.5 61.3 78.8 53.8 520 - 65 71.3 78.8 55 520 3: 1 71.3 72.5 80 56.3 520 15: 1 70 77.5 86.3 61.3 520 30: 1 70 70 81.7 61.7 715 - 76.3 76.3 90 76.3 715 3: 1 81.3 85 91.3 78.8 715 15: 1 80 81.3 91.3 75 715 30: 1 81.3 86.3 95 82.5 910 - 78.3 78.3 88.3 78.3 910 3: 1 81.3 87.5 90 78.8 910 15: 1 83.8 92.5 91.3 76.3 910 30: 1 77.5 92.5 95 76.3 Table 60b
% weed control 24 days after treatment with 450IS and oxalic acid Application rate (g ke / ha) g ke: g oxalic acid IPOLA Abuth Casob SEBEX 325 - 52,5 53.8 75 48.8 325 3: 1 62.5 62.5 76.3 56.3 325 15: 1 57.5 61.3 81.3 fifty 325 30: 1 58.8 58.8 81.3 41.3 520 - 71.3 73.8 83.8 60 520 3: 1 71.3 78.8 83.8 67.5 520 15: 1 68.8 70 82.5 57.5 520 30: 1 68.8 70 82.5 61.3 715 - 73.8 85 92.5 83.8 715 3: 1 86.3 96.3 92.5 77.5 715 15: 1 80 91.3 96.3 80 715 30: 1 77.5 85 93.8 78.8 910 - 81.3 77.5 90 75 910 3: 1 78.8 88.8 90 78.8 910 15: 1 83.8 90 93.8 82.5 910 30: 1 81.3 86.3 95 78.8 Table 60c
% weed control 24 days after treatment with 450I and oxalic acid Application rate (g ke / ha) g ke: g oxalic acid IPOLA Abuth Casob SEBEX 325 - 52,5 57.5 66.3 41.3 325 3: 1 53.8 55 63.8 40 325 15: 1 56.3 61.3 62.5 40 325 30: 1 55 56.3 63.8 41.3 520 - 61.3 67.5 75 52,5 520 3: 1 68.3 63.3 80 43.3 520 15: 1 71.3 68.8 78.8 47.5 520 30: 1 67.5 68.8 81.3 55 715 - 78.8 77.5 82.5 66.3 715 3: 1 82.5 90 86.3 67.5 715 15: 1 77.5 90 86.3 72.5 715 30: 1 77.5 80 88.8 73.8 910 - 75 80 83.8 63.8 910 3: 1 80 95 90 73.8 910 15: 1 80 83.8 86.3 72.5 910 30: 1 80 78.8 83.8 70

Table 60d
% weed control 24 days after treatment with Roundup UltraMax Dry without the addition of oxalic acid Application rate (g ke / ha) IPOLA Abuth Casob SEBEX 325 56.3 60 78.8 fifty 520 73.8 71.3 83.8 60 715 82.5 85 87.5 76.3 910 83.8 87.5 90 77.5

Composition 360I, including oxalic acid, had significantly higher efficacy against all species of test plants than composition 360I.

The 450IS composition comprising oxalic acid had significantly higher or similar efficacy as the 450IS composition against all species of plants tested, and the composition where the glyphosate to oxalic acid ratio was 3: 1 was substantially higher than other compositions containing oxalic acid.

Composition 450I, including oxalic acid, had significantly higher or similar efficacy as composition 450I, against all tested plant species.

Example 61

The effect of oxalic acid, included in composition 480I, composition 725K, and TD IQ, on the efficacy of these compositions against plants of Ipomoea angustifolia (IPOLA), Theofrasta teatraum (ABUTH), Cannabis sowing (SEBEX), millet blackberry (ECHCG) and astragalus serpus and astragalus was evaluated. (CASOB) and at various application rates and ratios of active ingredient to oxalic acid. Each of the compositions: composition 480I, composition 725K and composition TD IQ, prepared without oxalic acid, with a mass ratio of kephonoglyphosate: oxalic acid, constituting 3: 1, 15: 1 and 30: 1, was tested at the application rates of the active ingredient 325, 520, 715 and 910 g of active substance (ke) per hectare. Comparative compositions of Roundup UltraMax without the addition of oxalic acid were tested for efficacy against IPOLA, ABUTH, SEBEX, ECHCG and CASOB at application rates of active ingredient 325, 520, 715 and 910 g (ke) per hectare. The results, expressed as% destruction, are presented in tables 61 a, b, c and d.

Table 61a
% Weed control after treatment with 480I and oxalic acid Application rate (g ke / ha) g ke: g oxalic acid IPOLA Abuth SEBEX Echcg Casob 325 - 66.3 61.3 53.8 93.8 80 325 3: 1 63.8 70 41.3 94.8 80 325 15: 1 56.3 67.5 fifty 96.3 77.5 325 30: 1 62.5 63.8 48.3 98.5 75 520 - 70 75 60 98.8 81.3 520 3: 1 78.8 90 57.5 94.8 86.3 520 15: 1 78.8 80 58.8 99.5 85 520 30: 1 80 81.3 58.8 98.8 85 715 - 81.3 96 62.5 one hundred 91.3 715 3: 1 76.3 88.3 65 97.5 88.8 715 15: 1 78.8 88.8 65 97.5 93.8 715 30: 1 81.3 93.8 68.8 one hundred 92.5 910 - 86.3 98.5 67.5 one hundred 92.5 910 3: 1 86.3 95 71.3 99.8 90 910 15: 1 85 96.5 68.8 one hundred 91.3 910 30: 1 86.3 98 65 one hundred 91.3 Table 61b
% Weed control after treatment with 725K and oxalic acid Application rate (g ke / ha) g ke: g oxalic acid IPOLA Abuth SEBEX Echcg Casob 325 - fifty 55 35 70 45 325 3: 1 63.8 70 33.8 72.5 52,5 325 15: 1 56.3 61.3 31.3 68.8 48.8 325 30: 1 60 70 45 77.5 fifty 520 - 67.5 62.5 42.5 81.3 67.5 520 3: 1 73.8 75 38.3 85.3 62.5 520 15: 1 73.8 75 41.3 76.3 63.8 520 30: 1 70 75 38.8 81.3 57.5 715 - 71.3 73.8 38.8 80 63.8 715 3: 1 76.3 89.8 37.5 65 71.3 715 15: 1 75 81.3 37.5 76.3 67.5 715 30: 1 77.5 86.5 38.8 77.5 65 910 - 76.3 84.8 40 87.5 71.3 910 3: 1 82.5 97.5 35 80 67.5 910 15: 1 80 one hundred 46.3 88.5 72.5 910 30: 1 81.3 83.8 41.3 76.3 78.8 Table 61c
% Weed control after treatment with TD IQ and oxalic acid Application rate (g ke / ha) g ke: g oxalic acid IPOLA Abuth SEBEX Echcg Casob 325 - 65 72.5 55 98.8 81.3 325 3: 1 70 86.3 53.8 97.3 83.8 325 15: 1 70 76.3 52,5 92.3 80 325 30: 1 63.8 72.5 fifty 93.3 77.5 520 - 80 80 60 98.8 85 520 3: 1 82.5 80 60 97.5 85 520 15: 1 76.3 84.3 63.8 97 85 520 30: 1 82.5 75 58.8 92 77.5 715 - 81.3 90.8 65 one hundred 92.5 715 3: 1 85 92.3 65 one hundred 91.3 715 15: 1 86.3 93.5 61.3 one hundred 91.3 715 30: 1 80 78.8 66.3 99 93.8 910 - 86.3 95.3 67.5 one hundred 93.8 910 3: 1 87.5 98.8 71.3 one hundred 95 910 15: 1 85 92.5 72.5 one hundred 95 910 30: 1 86.3 97 68.8 one hundred 95

Table 61d
% weed control after treatment with Roundup UltraMax without the addition of oxalic acid Application rate (g ke / ha) IPOLA Abuth SEBEX Echcg Casob 325 63.8 65 51.7 98.3 80 520 80 75 61.3 97.5 85 715 80 91 67.5 99 93.8 910 86.3 97 71.3 one hundred 92.5

Composition 725K, including oxalic acid, had significantly higher efficacy against IPOLA, ABUTH and CASOB plants than composition 725K.

Compared to the TD IQ composition, the TD IQ composition containing oxalic acid had significantly higher or similar efficacy against all plant species except ECHCG, with a 3: 1 and 15: 1 ratio of kephoglyphosate to oxalic acid.

Composition 480I, including oxalic acid, had significantly higher efficacy or the same efficacy as composition 480I, against all tested plant species except for ECHCG.

Example 62

The effects of oxalic acid, included in composition 480I, composition 725K, and TD IQ, on the efficacy of these compositions against the plants of Theofrasta abutis (ABUTH), hempweed (SEBEX), narrow-leaved morning glory (IPOLA), prickly brisket (SIDSP) and sickle-like astragalus (SIDSP) were evaluated. CASOB) and at various application rates and ratios of the active ingredient to oxalic acid. Each of the compositions: composition 480I, composition 725K and composition TD IQ, prepared without oxalic acid, in mass ratios ke glyphosate: oxalic acid, constituting 3: 1, 15: 1 and 30: 1, was tested at a rate of application of the active ingredient of 420, 683, 946 and 1366 g of active substance (ke) per hectare. Comparative compositions of Roundup UltraMax without the addition of oxalic acid were tested for efficacy against IPOLA, ABUTH, SEBEX, ECHCG and CASOB at rates of application of the active ingredient 420, 683, 946 and 1366 g (ke) per hectare. The results are presented in tables 62 a, b, c and d.

Table 62a
% weed control after treatment with 480I and oxalic acid Application rate (g ke / ha) g ke: g oxalic acid Abuth SEBEX IPOLA SIDSP Casob 420 - 88.5 79.8 55 91.8 78.8 420 3: 1 82.3 80.5 61.3 93 72.5 420 15: 1 88.3 73.5 55 92.8 74.8 420 30: 1 90.8 75,5 51.3 96 81.3 683 - 93.5 91.3 63.8 96.8 81.3 683 3: 1 96.8 93.5 68.8 95.3 82.5 683 15: 1 92 93.3 68.8 96 80.5 683 30: 1 98.5 88.5 68.8 99.3 83.8 946 - 97.3 86.5 70.8 95.8 84 946 3: 1 99.3 95 77.5 97 83 946 15: 1 95.3 93 72 93.3 82.5 946 30: 1 98.8 95.3 72 98.3 82.3 1366 - 98.3 99.3 78.3 99.3 83 1366 3: 1 99.8 95.8 81.3 98.3 82.5 1366 15: 1 99.7 96.3 79.7 99 86.7 1366 30: 1 99.5 99.8 83.3 99.5 83.3 Table 62b
% weed control after treatment with 725K and oxalic acid Application rate (g ke / ha) g ke: g oxalic acid Abuth SEBEX IPOLA SIDSP Casob 420 - 68.8 3.8 42.5 81.3 46.3 420 3: 1 89.3 0 42.5 87.3 48.8 420 15: 1 74.8 6.3 42.5 92.5 45 420 30: 1 71.8 0 38.8 85.8 46.3 683 - 86.8 3.8 47.5 92.3 46.3 683 3: 1 97 3.8 fifty 92.5 48.8

683 15: 1 94 6.3 51.3 92.3 47.5 683 30: 1 93.3 5 57.5 92.3 fifty 946 - 93.5 10 60 96.8 51.3 946 3: 1 99.3 6.3 56.3 98 45 946 15: 1 93 7.5 67.5 98 53.8 946 30: 1 95.8 10 62.5 98 51.3 1366 - 97.3 7.5 70.3 98.3 55 1366 3: 1 99.5 11.3 65 90.8 51.3 1366 15: 1 98.3 fifteen 66.3 98 52,5 1366 30: 1 99.5 6.3 67.5 99 51.3 Table 62c
% weed control after treatment with TD IQ and oxalic acid Application rate (g ke / ha) g ke: g oxalic acid Abuth SEBEX IPOLA SIDSP Casob 420 - 91.5 72.5 51.3 90.5 82.5 420 3: 1 87.5 69.3 53.8 90.5 80.5 420 15: 1 93.3 77.5 56.3 90.3 79.8 420 30: 1 85.5 76.3 52,5 94.8 82.3 683 - 88.8 88.8 65.8 91.3 81.3 683 3: 1 99.3 94 65.8 98 78 683 15: 1 96 88.5 61.3 94 80.8 683 30: 1 93.5 89 65 90.8 82.5 946 - 92 93.8 72.5 96.3 85.3 946 3: 1 99.3 99.3 77.5 96.8 83.8 946 15: 1 99.5 97.3 68.8 96.3 82.5 946 30: 1 95.8 89.3 70 94.5 81 1366 - 99.5 96 74.5 98.5 81.3 1366 3: 1 99.5 97.5 77.8 98.3 81.8 1366 15: 1 97.5 97.5 75 99.3 83.8 1366 30: 1 one hundred 99.8 78.3 99.3 84

Table 62d
% weed control after treatment with Roundup UltraMax without the addition of oxalic acid Application rate (g ke / ha) Abuth SEBEX IPOLA SIDSP Casob 420 84.8 69 57.5 93 80.5 683 97 86.8 68.8 95.8 82.3 946 99.5 96 73.8 97 81 1366 97 97.5 80 96.8 83

Composition TD IQ, including oxalic acid, had significantly higher efficiency or the same effectiveness against plants IPOLA, ABUTH, SEBEX and SIDSP, as the composition TD IQ, and in particular, with a ratio of kef glyphosate to oxalic acid 3: one.

Composition 725K, including oxalic acid, had significantly higher efficacy or the same efficacy against IPOLA, ABUTH, SEBEX and SIDSP plants, as well as composition 725K.

Composition 480I, including oxalic acid, had significantly higher potency or the same potency against IPOLA, ABUTH, SEBEX and SIDSP plants as did 480I.

Example 63

The effects of oxalic acid, included in composition 480I, composition 725K, and TD IQ, on the efficacy of these compositions against plants of Crescent Astragalus (CASOB), Desmodium (DEDTO), Ipomoea Narcifolia (IPOLA), Cannabis sessenia (SEBEX), and Theofra Theophra (ABUT) were evaluated. ), with different application rates and ratios of the active ingredient to oxalic acid. Each of the compositions: composition 480I, composition 725K and composition TD IQ, prepared without oxalic acid, with a mass ratio of kephonoglyphosate: oxalic acid, constituting 3: 1, 15: 1 and 30: 1, was tested at the application rates of the active ingredient 420, 683, 946 and 1366 g of active substance (ke) per hectare. Comparative compositions of Roundup UltraMax without the addition of oxalic acid were tested at rates of application of the active ingredient 420, 683, 946 and 1366 g (ke) per hectare. The results are presented in tables 63 a, b, c and d.

Table 63a
% weed control after treatment with 480I and oxalic acid Application rate (g ke / ha) g ke: g oxalic acid Casob DEDTO IPOLA SEBEX Abuth 420 - 84 97 57.5 81.5 92 420 3: 1 81.5 94.3 55 80 94.3 420 15: 1 80.3 96 57.5 81 93.5 420 30: 1 78 96 52,5 79 89.8 683 - 84.5 98 66.3 87 99 683 3: 1 82 98 61.3 89.8 98 683 15: 1 80 96.8 65 82.5 99 683 30: 1 82.5 98 67.5 84.3 99 946 - 87.5 99 70 93.5 99 946 3: 1 86.5 99 72.5 92 99 946 15: 1 84.5 97 72 86.8 99 946 30: 1 85 98 71.3 88.5 99 1366 - 88.3 97 75.3 94 99 1366 3: 1 90.5 98 82.3 95.3 99 1366 15: 1 84 98 75.3 90.8 99 1366 30: 1 83.5 98 80.8 93.3 99 Table 63b
% weed control after treatment with 725K and oxalic acid Application rate (g ke / ha) g ke: g oxalic acid Casob DEDTO IPOLA SEBEX Abuth 420 - thirty 86.5 37.5 10 81.3 420 3: 1 28.8 79.5 35 10 83.8 420 15: 1 thirty 80 42.5 10 88 420 30: 1 31.3 84.3 41.3 10 82 683 - 36.3 87.3 45 10 90.5 683 3: 1 36.3 84.8 37.5 10 92.8 683 15: 1 26.3 87.5 46.3 10 92 683 30: 1 36.3 96 46.3 10 95.8 946 - 36.3 93.5 45 10 93.8 946 3: 1 37.5 88.5 46.3 10 95.8 946 15: 1 35 93.3 48.8 10 96.8 946 30: 1 35 90.3 46.3 10 94.8 1366 - 40 97 51.3 10 97 1366 3: 1 38.8 94.5 fifty 10 93.5 1366 15: 1 41.3 95.8 56.3 10 96.8 1366 30: 1 42.5 95.3 62.5 12.5 95.8 Table 63c
% weed control after treatment with TD IQ and oxalic acid Application rate (g ke / ha) g ke: g oxalic acid Casob DEDTO IPOLA SEBEX Abuth 420 - 82 96 48.8 77 89.3 420 3: 1 82.3 96 55 75,5 91.8 420 15: 1 80.5 96 56.3 76.8 86.8 420 30: 1 85.8 96 52,5 79.8 93.5 683 - 80.8 98 60.8 85 98 683 3: 1 85.5 96.3 67.5 86.8 99 683 15: 1 86.5 98 69.5 86.3 99 683 30: 1 84 99 65 88 99 946 - 84.3 99 66.3 85 99 946 3: 1 86.3 97 76.5 96.8 99 946 15: 1 84.8 99 74.5 89.5 99 946 30: 1 85.3 99 72 90.5 99 1366 - 89.8 98 69.5 98 99 1366 3: 1 86.5 99 77.5 99 98 1366 15: 1 87.5 99 81.3 99 99 1366 30: 1 86.8 98 81 98 98 Table 63d
% weed control after treatment with Roundup UltraMax without the addition of oxalic acid Application rate (g ke / ha) Casob DEDTO IPOLA SEBEX Abuth 420 82.5 97 56.3 79 90 683 85.5 97 63.8 84 98 946 90.5 99 72.5 89 99 1366 90.3 99 80 99 99

Composition TD IQ, including oxalic acid, had significantly higher efficacy against plants IPOLA and SEBEX, CASOB and ABUTH, than composition TD IQ, with a ratio of ke glyphosate to oxalic acid 30: 1.

Composition 725K, including oxalic acid, had significantly higher efficacy against plants IPOLA, and ABUTH, than composition 725K at a ratio of ke glyphosate to oxalic acid of 15: 1 and 30: 1.

Example 64

We evaluated the effect of oxalic acid included in the 480I composition, 725K composition, and TD IQ composition on the effectiveness of these compositions against plants of Ipomoea angustifolia (IPOLA), Teofrasta tumeric (ABUTH), sickle-like astragalus (CASOB), and hemp hemp (SEBEX) at various application rates and the relationship of kef glyphosate to oxalic acid. Each of the compositions 480I, 725K and TD IQ, prepared without oxalic acid, with a mass ratio of kef glyphosate: oxalic acid constituting 3: 1, 15: 1 and 30: 1, was tested at the application rates of the active ingredient 455, 650, 845 and 1040 g of active substance (ke) per hectare. Comparative Roundup UltraMax formulations without the addition of oxalic acid were tested at application rates of 455, 650, 845 and 1040 g (ke) of active ingredient per hectare. The results are presented in tables 64 a, b, c and d.

Table 64a
% weed control after treatment with 480I and oxalic acid Application rate (g ke / ha) g ke: g oxalic acid IPOLA Abuth Casob SEBEX 455 - 53.8 53.8 90 70 455 3: 1 57.5 52,5 86.3 65 455 15: 1 58.8 61.3 86.3 67.5 455 30: 1 61.3 62.5 88.8 61.3 650 - 58.8 62.5 88.8 90 650 3: 1 60 58.8 92.5 82.5 650 15: 1 62.5 63.8 88.8 87.5 650 30: 1 58.8 60 86.3 62.5 845 - 80 71.3 92.5 88.8 845 3: 1 67.5 68.8 90 83.8 845 15: 1 70 68.8 90 82.5 845 30: 1 72.5 70 88.8 82.5 1040 - 87.5 83.8 93.8 90 1040 3: 1 81.3 83.8 95 95 1040 15: 1 85 72.5 97.5 90 1040 30: 1 81.3 73.8 90 86.3 Table 64b
% weed control after treatment with 725K and oxalic acid Application rate (g ke / ha) g ke: g oxalic acid IPOLA Abuth Casob SEBEX 455 - 60 56.3 70 41.3 455 3: 1 57.5 56.3 66.3 45 455 15: 1 57.5 57.5 66.3 40 455 30: 1 58.8 56.3 63.8 43.8 650 - 57.5 56.3 72.5 47.5 650 3: 1 62.5 65 68.8 56.3 650 15: 1 61.3 58.8 71.3 45 650 30: 1 65 63.8 75 46.3 845 - 71.3 70 68.8 42.5 845 3: 1 66.3 72.5 75 57.5 845 15: 1 62.5 66.3 73.8 57.5 845 30: 1 61.3 61.3 80 fifty 1040 - 76.3 76.3 82.5 63.8 1040 3: 1 71.3 75 77.5 48.8 1040 15: 1 78.8 73.8 76.3 48.8 1040 30: 1 68.8 80 76.3 48.8 Table 64c
% weed control after treatment with TD IQ and oxalic acid Application rate (g ke / ha) g ke: g oxalic acid IPOLA Abuth Casob SEBEX 455 - 62.5 58.8 91.3 76.3 455 3: 1 62.5 63.8 91.3 73.8 455 15: 1 65 65 87.5 72.5 455 30: 1 61.3 58.8 86.3 81.3 650 - 62.5 65 91.3 91.3 650 3: 1 67.5 73.8 91.3 87.5 650 15: 1 63.8 71.3 88.8 91.3 650 30: 1 63.8 68.8 90 81.3 845 - 75 68.8 92.5 92.5 845 3: 1 67.5 68.8 92.5 87.5 845 15: 1 68.8 73.8 95 93.8 845 30: 1 72.5 71.3 91.3 90 1040 - 86.3 76.3 91.3 90 1040 3: 1 82.5 77.5 92.5 83.8 1040 15: 1 83.8 75 93.8 86.3 1040 30: 1 85 72.5 96.3 93.8

Table 64d
% weed control after treatment with Roundup UltraMax without the addition of oxalic acid Application rate (g ke / ha) IPOLA Abuth Casob SEBEX 455 66.3 61.3 93.8 70 650 66.3 68.8 91.3 90 845 81.3 68.8 95 88.8 1040 82.5 75 91.3 93.8

Composition 725K, including oxalic acid, had significantly higher efficacy or the same potency against ABUTH and SEBEX plants as composition 725K, with a 3: 1 and 15: 1 ratio of glyphosate ke to oxalic acid.

Composition TD IQ, including oxalic acid, had significantly higher efficacy against ABUTH plants than composition TD IQ, with a ratio of ke glyphosate to oxalic acid of 3: 1 and 15: 1.

Example 65

The effect of oxalic acid, included in the 360I composition, the 450IS composition and the 450I composition, on the effectiveness of these compositions against plants of Ipomoea angustifolia (IPOLA), Theofrastus theutra (ABUTH), Astragalus crescent (CASOB) and hemp hemp (SEBEX) was evaluated at various application rates and the relationship of kef glyphosate to oxalic acid. Each of the compositions 360I, 450IS and 450I, prepared without oxalic acid, with a mass ratio of kephonoglyphosate: oxalic acid, constituting 3: 1, 15: 1 and 30: 1, was tested at the application rates of the active ingredient 455, 650, 845 and 1040 g of active substance (ke) per hectare. Comparative Roundup UltraMax formulations without the addition of oxalic acid were tested at application rates of 455, 650, 845 and 1040 g (ke) of active ingredient per hectare. The results are presented in tables 65 a, b, c and d.

Table 65a
% weed control after treatment with 360I and oxalic acid Application rate
(g ke / ha) glyphosate: SCH IPOLA Abuth Casob SEBEX 455 - 51.3 60 83.8 63.8 455 3: 1 61.3 63.8 77.5 72.5 455 15: 1 58.8 58.8 76.3 61.3 455 30: 1 58.8 57.5 75 71.3 650 - 61.3 70 85 77.5 650 3: 1 61.3 66.3 88.8 78.8 650 15: 1 63.8 66.3 85 78.8 650 30: 1 62.5 72.5 81.3 70 845 - 67.5 80 90 81.3 845 3: 1 68.8 76.3 91.3 77.5 845 15: 1 62.5 70 85 72.5 845 30: 1 68.8 78.8 91.3 76.3 1040 - 73.8 81.3 96.3 91.3 1040 3: 1 76.3 78.8 96.3 91.3 1040 15: 1 76.3 88.8 95 86.3 1040 30: 1 78.8 81.3 95 91.3 Table 65b
% weed control after treatment with 450IS and oxalic acid Application rate
(g ke / ha) g ke: g oxalic acid IPOLA Abuth Casob SEBEX 455 - 58.8 73.8 85 68.8 455 3: 1 63.8 70 82.5 60 455 15: 1 61.3 70 81.3 67.5 455 30: 1 57.5 63.8 77.5 62.5 650 - 60 73.8 86.3 82.5 650 3: 1 63.8 73.8 81.3 76.3 650 15: 1 66.3 76.3 88.8 83.8 650 30: 1 63.8 76.3 87.5 76.3 845 - 77.5 75 92.5 82.5 845 3: 1 78.8 80 95 83.8 845 15: 1 75 82.5 91.3 82.5 845 30: 1 75 73.8 91.3 82.5 1040 - 88.8 85 93.8 85 1040 3: 1 83.8 81.3 95 85 1040 15: 1 81.3 88.8 93.8 87.5 1040 30: 1 76.3 80 88.8 83.8

Table 65c
% weed control after treatment with 450I and oxalic acid Application rate
(g ke / ha) g ke: g oxalic acid IPOLA Abuth Casob SEBEX 455 - 53.8 56.3 60 43.8 455 3: 1 61.3 68.8 72.5 47.5 455 15: 1 56.3 • 56.3 63.8 48.8 455 30: 1 56.3 58.8 63.8 48.8 650 - 57.5 70 71.3 46.3 650 3: 1 60 72.5 76.3 70 650 15: 1 66.3 71.3 78.8 62.5 650 30: 1 60 83.8 72.5 58.8 845 - 65 76.7 81.7 78.3 845 3: 1 73.8 76.3 86.3 77.5 845 15: 1 70 75 82.5 76.3 845 30: 1 75 80 83.8 71.3 1040 - 76.3 76.3 85 81.3 1040 3: 1 82.5 82.5 93.8 86.3 1040 15: 1 81.3 82.5 86.3 80 1040 30: 1 78.8 85 85 85

Table 65d
% weed control after treatment with Roundup UltraMax without the addition of oxalic acid Application rate (g ke / ha) IPOLA Abuth Casob SEBEX 455 60 61.3 83.8 58.8 650 61.3 73.8 85 70 845 77.5 77.5 87.5 75 1040 78.8 90 93.8 81.3

Composition 450I, including oxalic acid, had significantly higher efficacy against all plant species tested than composition 450I, and a composition having a glyphosate to oxalic acid ratio of 3: 1 was more effective than other compositions containing oxalic acid.

As for IPOLA, the 360I composition comprising oxalic acid had significantly higher efficacy against all plant species tested than the 360I composition, and the composition having a glyphosate to oxalic acid ratio of 3: 1 was more effective than other compositions containing oxalic acid. acid. Composition 360I, used against other weeds, basically did not show a significant increase in efficiency compared with compositions containing oxalic acid.

For all types of plants, the 450IS composition having glyphosate to oxalic acid ratios of 3: 1 and 15: 1 had basically the same or higher efficiency than the 450IS composition. For all plant species, the effectiveness of the 450IS composition having a glyphosate to oxalic acid ratio of 30: 1 was lower than the effectiveness of the 450IS composition.

Example 66

The effect of organic bases in combination with oxalic acid in reservoir mixtures containing the potassium salt of glyphosate and the alkyl ether-amine surfactant M-1415E13-2 (from Tomah) was evaluated. Glyphosate concentrations for each composition were 62.7 g ke per liter.

Table 66a Composition Component 1 wt.% Component 2 wt.% 630A2L S1 2 - - 630B6N S1 2 Oxalic acid 0.3

The compositions shown in table 66a and the comparative composition Roundup UltraMax were applied to edible plants (Cyperus esculentis, CYPES). The results, the average of all repetitions of experiments for each treatment, are presented in tables 66b.

Table 66b
% destruction of CYPES Composition 200 g ke / ha 400 g ke / ha 600 g ke / ha 800 g ke / ha 630A2L 72.8 80,4 80,4 86 630B6N 63.7 81.8 76 84.7 Roundup ultramax 75.8 70.6 79.7 91.7

The addition of 0.03% oxalic acid to reservoir mixtures of an alkoxylated amine surfactant and glyphosate potassium salt did not lead to a synergistic edible effect on the plants.

Example 67

The durability of Roundup UltraMax and oxalic acid with respect to rainfall was evaluated at a mass ratio of kef glyphosate: oxalic acid equal to 15: 1. Roundup UltraMax compositions were used at application rates of 300 and 500 g ke / ha and evaluated in the absence of rain, at a rainfall of 0.25 inches for one hour after treatment, and at a rainfall of 0.25 inches for two hours after treatment . The results are presented below in table 67a.

Table 67a
% Destruction of ABUTH 15 days after processing Compositions Roundup UltraMax. Lack of rain Rainfall 0.25 "in 1 hour Rainfall 0.25 "in 2 hours 300 g ke / ha 84.6 32,5 49.1 500 g ke / ha 94.8 55.7 72.5 300 g ke / ha + 20 g / ha oxalic acid 90.8 24.2 40.8 300 g ke / ha + 30 g / ha oxalic acid 95.5 fifteen 50.8 500 g ke / ha + 33 g / ha oxalic acid 96.2 42.5 63.3 500 g ke / ha + 50 g / ha oxalic acid 99.3 48.3 61.7

A slight increase in efficiency was observed for a composition containing oxalic acid in the absence of rain. When processing the plants of the Theophrastus cannibal, oxalic acid did not provide greater resistance to precipitation than Roundup UltraMax during one to two hours of precipitation.

Example 68

The effect of oxalic acid and ammonium oxalate on the systems of cationogenic and nonionic surfactants in the compositions of the glyphosate ammonium salt was evaluated. In addition, aqueous concentrate compositions were tested, prepared as described in Example 21 and presented in Table 21a. In each composition, the concentration of glyphosate ammonium salt was 62 g kef of glyphosate per liter, and the molar ratio of oxalate to cationic surfactant was greater than 10. Compositions 071Е1М-071Р9G and comparative compositions AMM-GLY1S, AMM-GLY2S and Roundup UltraMax were applied to plants of the Theroprastus Theofrast (ABUTH), and the results are presented in table 68a. Compositions 071A5V, 071E1M and 071F5W were again tested compared to the reference composition AMM-GLY3S at higher application rates on ABUTH and, in addition, these compositions were applied to plants of dandelion (TAROF) and white clover (MEUSS), and the results are shown in tables 69b -d. Compositions 071Q1A-071Z2C and 071AA2N-071AJ1Q and comparative compositions AMM-GLY1S, AMM-GLY2S and Roundup UltraMax were applied to ABUTH, and the results are presented in tables e and f. In each trial, treatment results were averaged over all replicates for each treatment.

Table 68a
% Inhibition of ECHCF 15 days after treatment Composition 75 g ke / ha 100 g ke / ha 200 g ke / ha 400 g ke / ha 071I6B twenty 57.5 75 85.8 071J5D 25 52,5 72.5 88 071K6J 9.2 fifty 67.5 75.8 071L1K 32,5 59.2 75 89.7 071M3X 45.8 59.2 70.8 83.3 071N7U 40 50.8 70 83.3 071O2W 28.3 45 64,2 75 071P9G 48.3 61.7 76.7 94.7 AMM-GLY2S 0 5 35 60.8 AMM-GLY1S 25 47.5 67.5 85 Ultramax thirty 49.2 68.3 86.7

The effectiveness of the compositions against ABUTH containing cationic surfactants (S51) with the addition of oxalic acid or ammonium oxalate exceeded the effectiveness of the compositions without oxalate. Mixtures of a cationic surfactant: a non-ionic surfactant comprising 60:40 and 80:20 with the addition of oxalic acid or ammonium oxalate provided an anti-ABUTH potency greater than that of standard or non-oxalate formulations. Compositions containing mixtures of a cationic surfactant: a non-ionic surfactant in a ratio of 60:40 with the addition of oxalic acid had excellent efficacy against ECHCF. The addition of a nonionic surfactant to a cationic surfactant resulted in a synergistic effect on ECHCF, in contrast to the action of only one cationic surfactant.

Table 68b
% Inhibition of ABUTH 19 days after treatment Composition 100 g ke / ha 200 g ke / ha 400 g ke / ha 800 g ke / ha 071A5V 0 45 78.3 90 071E1M thirty 68.3 76.7 96.7 071F5W 55 80 88.3 95 AMM-GLY3S 0 46.7 78.3 86.7 Table 68c
% Inhibition of TAROF 19 days after treatment Composition 100 g ke / ha 200 g ke / ha 400 g ke / ha 800 g ke / ha 071A5V 10 fifty 70 86 071E1M 8.3 60 73.3 87.7 071F5W 8.3 73.3 85 one hundred 071E1M 11.7 60 65 82.7 Table 68d
% Inhibition of MEUSS 19 days after treatment Composition 100 g ke / ha 200 g ke / ha 400 g ke / ha 800 g ke / ha 071A5V 5 13.3 21.7 33.3 071E1M 6.7 twenty thirty 36.7 071F5W 8.3 fifteen 25 38.3 AMM-GLY3S 0 8.3 fifteen 23.3

Based on the data presented in Tables 68b-d, the most effective composition against Theofrast and Dandelion rope was 071F5W, followed by 071E1M and 071A5V. None of the evaluated compositions had an effective inhibitory effect on white melilot.

Table 68e
% Inhibition of ABUTH Composition 75 g ke / ha 100 g ke / ha 200 g ke / ha 400 g ke / ha 071Q1A 10 33.3 75 87.5 071R5V 27.5 thirty 78.3 87.5 071T6N 79.2 81.7 89.2 95.8 071U8M 48.3 78.3 80 90.8 071V3Y 84.2 85 90 96.7 071W2X 47.5 68.3 83.3 92.2 071X0D 82.5 82.5 91.7 98.7 071Z2C 85.8 86.7 94.2 98.7 AMM-GLY2S 0 0 60 80.8 AMM-GLY1S 0 0 70 84.2 Ultramax 0.8 21.7 80 89.2

Based on the data presented in table 68e, each of the compositions 071Z2C, 071V3Y, 071X0D, 071T6N and 071U8M was more effective than standard compositions. Compared to the data presented in Tables 21b and 68b, similar superior performance was achieved, but using a different cationic surfactant.

Table 68f
% Inhibition of ABUTH Composition 75 g ke / ha 100 g ke / ha 200 g ke / ha 400 g ke / ha 071AA2N 24.2 52,5 80 88.3 071AB7H fifty 65.8 85 93.7 071AD4N 84.2 87.5 92.5 98.7 071AE3F 65.8 74,2 85.8 93 071AF7B 81.7 86.7 94.2 99,2 071AG8O fifty 65 84.2 87.5 071AH6X 55 64,2 85.8 94.7 071AJ1Q 84.2 86.7 92.5 99,2 AMM-GLY2S 0 0 75 83.3 AMM-GLY1S 0.8 46.7 77.5 87.5 Ultramax 25.8 65 85 94.3

Based on the data presented in tables 68f, all compositions except 071AA2N were more effective than standard compositions. Compared to the data presented in Tables 21b and 68b, similar superior performance was achieved, but using a different cationic surfactant.

Example 69

The effects of oxalic acid and ammonium sulfate on cationic: nonionic surfactant systems in dry compositions of glyphosate ammonium salt were evaluated. Dry concentrate compositions were prepared containing the glyphosate ammonium salt and the auxiliary ingredients described in Example 20 and shown in Table 20a, and these compositions were then applied to hemp plant (SEBEX) and barbed brisket (SIDSP) plants. The results, the average of all repetitions of experiments for each treatment, are presented in tables 69a and 69b.

Table 69a
% Inhibition of SEBEX Composition 600 g ke / ha 800 g ke / ha 1000 g ke / ha 2000 g ke / ha 664A4D 75 75.8 76.7 82.5 664B5T 73.3 76.6 78.3 89.7 664C6G 70 72.5 73.3 85 AMM-GLY2S 0 0 5 5.8 460I 2,5 6.7 7.5 22.5 Ultramax 70 75 77.5 83.3 IPA-GLY 70.8 75 77.5 80 470K 73.3 75.8 76.7 80 AMM-GLY1S 70 72.5 75.8 80 650A 75 77.5 76.7 80 AMM-GLY3S 69.2 72.5 75 76.7

Each of the compositions 664A4D, 664B5T and 664C6G was more effective than standard compositions AMM-GLY2S and 460I. All other standard and test compositions had similar efficacy.

Table 69b
% SIDSP Inhibition Composition 100 g ke / ha 200 g ke / ha 400 g ke / ha 800 g ke / ha 664A4D 33.3 51.7 65.0 84.2 664B5T 46.7 67.5 72.5 89.2 664C6G 40,0 52,5 70.0 86.7 AMM-GLY2S 5,0 40,0 45.0 60.0 460I 25.0 51.7 60.8 71.7 Ultramax 54,2 68.3 84.2 95.2 IPA-GLY 56.7 81.7 90.0 95.5 470K 55.0 71.7 85.8 93.3 AMM-GLY1S 35.8 63.3 73.3 85.0 650A 49.2 61.7 75.0 86.7 AMM-GLY3S 49.2 67.5 82.5 91.7

Compositions 664A4D and 664C6G were not effective, as were Roundup UltraMax.

Example 70

The effect of ammonium oxalate on the cationogenic: nonionic surfactant systems in the glyphosate ammonium salt compositions was evaluated. Liquid compositions were prepared with the exception of 483E7T, containing the glyphosate ammonium salt and the auxiliary ingredients shown in Table 70a. The concentration of glyphosate ammonium salt in each composition was 62 g ke / l. Composition 483E7T was a dry composition containing 68% ke ammonium salt of glyphosate.

Table 70a Composition Component 1 wt.% Component 2 wt.% Component 3 wt.% 095A3C S69 0.73 S50 0.49 NH ₄ oxalate 0.77 095I8J S69 0.49 S50 0.73 NH ₄ oxalate 0.77 095C6H S69 0.73 S47 0.49 NH ₄ oxalate 0.77 095J2L S69 0.73 S50 0.49 - - 095K9O S69 0.73 S47 0.49 - - 095F8S S70 0.73 S50 0.49 NH ₄ oxalate 0.77 483E7T S69 5.66 S50 7.94 NH ₄ oxalate 0.77

The compositions shown in Table 70a and the comparative compositions UltraMax and AMM-GLY3S were applied to Indian mustard (BRSJU), Theofrasta (ABUTH) rosemary and millet blackberry (ECHCF) plants. The results, the average of all repetitions of experiments for each treatment, are presented in tables 70b-d.

Table 70b
% Inhibition of BRSJU 17 days after treatment Composition 100 g ke / ha 200 g ke / ha 400 g ke / ha 600 g ke / ha 095A3C 28.3 57.5 81.7 89.2 095I8J thirty 66.7 83.3 88.3 095C6H 35 75 85.8 91.7 095J2L 21.7 79.2 84.2 87.5 095K9O 11.7 fifty 74,2 92.2 095F8S 26.7 75 88 90.8 483E7T 26.7 52,5 81.7 84.2 725K 0 5 30.8 61.7 Ultramax fifteen 54,2 77.5 88.8 AMM-GLY3S 18.3 47.5 79.2 90.5

Each of the compositions 095C6H and 095F8S was more effective than standard compositions, as well as composition 483E7T.

Table 70c
% Inhibition of ABUTH 14 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 095A3C 84.2 90 94.2 97.7 095I8J 84.2 89.2 94.2 98.5 095C6H 77.5 86.7 90.8 96.2 095J2L 84.2 87.5 90 96.2 095K9O 3.3 26.7 82.5 84.2 095F8S 87.5 90.8 96 99 483E7T 82.5 90 90.8 96.5 725K 0 0 0 10 Ultramax 10 63.3 85 90.7 AMM-GLY3S 10 68.3 85 85.8

All compositions, with the exception of 095K9O, had higher efficiency compared to standard compositions. The most effective were 095F8S, 095A3C and 095I8J.

Table 70d
% Inhibition of ECHCF 14 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 095A3C 18.3 65 90.8 91.3 095I8J 24.2 64,2 83.3 87.2 095C6H 1.7 57.5 66.7 67.5 095J2L 2.5 65.8 70.8 78.3 095K9O 8.3 37.5 65.8 67.5 095F8S 40 65 72.5 86.7 483E7T 11.7 65 76.7 80.8 725K 0 1.7 17.5 26.7 Ultramax 5 46.7 63.3 65 AMM-GLY3S 5 57.5 66.7 73.3

Each of the compositions 095A3C, 095I8J and 095F8S had higher efficiency than standard and other compositions.

Example 71

The effect of ammonium oxalate on cationic: nonionic surfactant systems in the glyphosate ammonium salt compositions was evaluated. Compositions were obtained containing the ammonium salt of glyphosate and the auxiliary ingredients shown in table 71a. The concentration of glyphosate ammonium salt in each composition was 62 g ke / l.

Table 71a Composition Component 1 wt.% Component 2 wt.% Component 3 wt.% 085A4M S69 1.22 - - - - 085B6J S50 1.22 - - - - 085C2I S69 0.73 S50 0.49 - - 085D6G S69 1.22 - - NH ₄ oxalate 0.77 085E4K S50 1.22 - - NH ₄ oxalate 0.77 085F5V S69 0.73 S50 0.49 NH ₄ oxalate 0.77

The compositions shown in table 71a, and the comparative UltraMax compositions and compositions 725K and AMM-GLY3S were applied to the plants of the Theofrasta abutis (ABUTH) and the blackberry rooster millet (ECHCF). The results, average for all replicates of experiments for each treatment, are presented in tables 71b and c.

Table 71b
% Inhibition of ABUTH Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 085A4M 15.8 49.2 75 90 085B6J 53.3 75 91.7 95.2 085C2I 50.8 75.8 92.5 96.5 085D6G 62.5 82.5 93.3 97 085E4K 70 87.5 94.2 97.3 085F5V 71.7 90.8 96.2 98.7 725K 0.8 12.5 55.8 60.8 Ultramax 20.8 65 82.5 91.7 AMM-GLY3S 8.3 38.3 65 85.8 Table 71c
% Inhibition of ECHCF Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 085A4M 35 62.5 81.7 90.8 085B6J thirty 56.7 75.8 84.2 085C2I 50.8 63.3 83.3 89.2 085D6G 31.7 54,2 72.5 85 085E4K 32,5 59.2 71.7 80 085F5V 45.8 61.7 85 91.3 725K 1.7 43.3 52,5 63.3 Ultramax 33.3 66.7 79.2 85.8 AMM-GLY3S 23.3 57.5 65 81.7

All compositions containing ammonium oxalate had higher efficacy against Theofrasta cannabis plants compared to compositions not containing ammonium oxalate. Regarding the effect of cockerel millet on the blackberry, the presence of ammonium oxalate did not give any significant increase in efficiency compared to compositions based on a single surfactant and containing either only cationogenic or only nonionic surfactant. Composition 085F5V was most effective against weeds of both species. All the data presented suggest that there are three ways of synergistic interaction between a cationic surfactant, a nonionic surfactant, and ammonium oxalate.

Example 72

The effectiveness of dry compositions of the ammonium salt of glyphosate containing systems of cationogenic: nonionic surfactants and inert substances was evaluated in the field. Compositions were obtained containing the ammonium salt of glyphosate in a concentration expressed in wt.% Ke and the auxiliary ingredients shown in table 72a. The concentration of glyphosate ammonium salt in each composition was 62 g ke / l.

Table 72a Composition Glyphosate% Component 1 wt.% Component 2 wt.% Component 3 wt.% 633R5Z 68 S72 11.6 S76 9.5 - - 634P7N 65 S71 13,4 S77 11.0 Sodium Sulfite / S74 0.4 /
0.1 636H4C 72 - - S78 17,2 Sodium Sulfite / S74 0.4 /
0.1 637B9K 72 S50 5.2 S69 12.0 Sodium Sulfite / S74 0.4 /
0.1 768I9M 65 S73 8.0 S13 8.0 Ammonium sulfate 10.0 769О4G 71 S61 2.0 S64 10.0 Oxalic acid 8.0 483D6S 68 S50 7.9 S69 5.7 Diammonium oxalate 8.3 420A3V 68 - - S75 21 Sodium sulfite 0.4

The compositions shown in table 72a, including comparative composition 420A3V (AMM-GLY3S), were applied to plants of amaranth (AMAQU), porcine fingernail (Cynodon dactylon, CYNDA), sweet clover (MEUSS) and bird mountain (Polygonum aviculare, POLAV) at rates applications of 960 g / ha, 1156 g / ha and 1564 g / ha. The results, the average of all replicates of the experiments for each treatment and for each plant species, as well as the total average for all plant species are presented in table 72b.

Table 72b
% Inhibition Composition AMAQU CYNDA MEUSS POLAV General 633R5Z 65.3 50.3 53.5 39.6 52.8 634P7N 70.3 58.7 49.1 37.1 55.1 636H4C 63,2 58.3 49.5 35 51.7 637B9K 67.3 53 48,2 40,4 53,2 768I9M 68,2 57.7 48.5 42.1 54.3 769O4G 61.8 59 42.8 36.3 51,4 483D6S 75 60.9 58.1 - 65.6 420A3V 65.8 47.3 51.3 27.5 49.4

All the compositions had a more effective effect on the plants of the fingernail (Cynodon dactylon, CYNDA) and birdlance (Polygonum aviculare, POLAV) than the standard composition 420A3V, with the total percentage inhibition calculated as the average percentage inhibition for all plant species tested. As for the highlander (AMAQU), the compositions 634P7N and 483D6S were more effective than the standard composition 420A3V (AMM-GLY3S) and ensured the destruction of plants by more than 85%.

Example 73

The effect of oxalic acid was evaluated in compositions with a high loading of glyphosate potassium salt containing ether-amine surfactants in the presence of alkyl polyglucosides. Compositions were prepared containing the potassium salt of glyphosate at a concentration of 540 g ke / l.

Table 73a Composition Component 1 wt.% Component 2 wt.% Component 3 wt.% 687A3C S79 10 - - - - 687B9L S32 10 - - - - 687C2F S79 10 - - Oxalic acid one 687D1Y S32 10 - - Oxalic acid one 687E4Z S79 6 S32 four Oxalic acid one 687F0M S79 four S32 6 Oxalic acid one 687G4I S79 6 S32 5 Oxalic acid one

The compositions shown in table 73a and comparative compositions 479K, UltraMax, 470K and 540KS were applied to Indian mustard plants (BRSJU). The results, the average of all replicates of the experiments for each treatment and for each plant species, as well as the total average for all plant species are presented in table 73b.

Table 73b
% Inhibition of BRSJU 14 days after treatment Composition 100 g ke / ha 200 g ke / ha 400 g ke / ha 800 g ke / ha 687A3C 34.2 69.2 82.5 89 687B9L 44,2 57.5 75 82.5 687C2F 68.3 71.7 85 94.5 687D1Y 70 70.8 77.5 87.5 687E4Z 60 73.3 79.2 94.7 687F0M 72.5 73.3 81.7 85.8 687G4I 74,2 75 87.5 93.3 479K 0 14.2 56.7 73.3 Ultramax 60 76.7 83.3 90 470K 33.3 70.8 83.3 88.3 540KS 45 72.5 88.8 91.3

Compositions 687C2F and 687G4I had an efficiency similar to that of the standard composition 540KS. Compositions 687A2C and 687E4Z had lower efficiency, and their effect was similar to that of standard UltraMax and 470K compositions.

Example 74

The efficacy of oxalic acid was re-evaluated in compositions with a high loading of glyphosate potassium salt containing ether-amine surfactants in the presence of alkyl polyglucosides. Each of the compositions 687A3C-687G4I contained a potassium salt of glyphosate at a concentration of 540 g ke / l. Two additional compositions, 079AQ4 and 083DR7, were also evaluated. Composition 079AQ4 contained 480 g ke / l potassium salt of glyphosate and 2% propylene glycol. In composition 079AQ4 and 083DR7, a stoichiometric amount of hydrochloric acid was added to convert the surfactants S80 and S81 to their corresponding HCl salt. Composition 083DR7 contained 365 g ke / l of the glyphosate isopropylamine salt.

Table 74a Composition Component 1 wt.% Component 2 wt.% Component 3 wt.% 687A3C S79 10 - - - - 687C2F S79 10 - - Oxalic acid one 687D1Y S32 10 - - Oxalic acid one 687E4Z S79 6 S32 four Oxalic acid one 687F0M S79 four S32 6 Oxalic acid one 687G4I S79 6 S32 5 Oxalic acid one 079AQ4 S80 5 S82 2 S5 6 083DR7 S81 2.25 S32 5 NH ₄ oxalate 3

The compositions shown in table 74a and comparative compositions 479K, Roundup UltraMax and 470K were applied to prickly brisket plants (SIDSP). The results, the average of all replicates of the experiments for each treatment and for each plant species, as well as the total average for all plant species are presented in table 74b.

Table 74b
% SIDSP Inhibition 14 Days After Treatment Composition 100 g ke / ha 200 g ke / ha 400 g ke / ha 800 g ke / ha 687A3C 49.2 77.5 85 92.2 687C2F 65 79.2 90.8 95 687D1Y 46.7 66.7 78.3 87.5 687E4Z 61.7 72.5 85 94.2 687F0M 53.3 57.5 78.3 92.5 687G4I 56.7 79.2 88 95.5 079AQ4 62.5 70 85 93.3 083DR7 65.8 78.3 92.5 96.5 479K twenty 57.5 65.8 79.2 Ultramax 55 76.7 84.2 94 470K 46.7 78.3 82.5 94.3

All 687D1Y and 687F0M compositions had higher efficacy than standard UltraMax and 470K compositions. The lowest efficiency was the standard composition 479K.

Example 75

The effects of ammonium oxalate and oxalic acid on cationic: nonionic surfactant systems in the glyphosate ammonium salt compositions were evaluated. Compositions were obtained containing the ammonium salt of glyphosate and the auxiliary ingredients shown in table 75a. The concentration of glyphosate ammonium salt in each composition was 62 g ke / l.

Table 75a Composition Component 1 wt.% Component 2 wt.% Component 3 wt.% 082A2V S35 1.14 - - - - 082B6G S35 0.57 S50 0.57 - - 082C7H S35 0.57 S50 0.57 NH ₄ oxalate 0.76 082D4F S35 0.57 S50 0.57 Oxalic acid 0.80 082E9K S35 0.52 S50 0.70 - - 082F6B S35 0.52 S50 0.70 NH ₄ oxalate 0.70 082G3S S35 0.52 S50 0.70 Oxalic acid 0.76

The compositions shown in Table 75a and the comparative compositions Roundup UltraMax, AMM-GLY2S and AMM-GLY3S were applied to hemp plant (SEBEX). The results, the average of all replicates of the experiments for each treatment and for each plant species, as well as the total average for all plant species are presented in table 75b.

Table 75b
% Inhibition of SEBEX 19 days after treatment Composition 100 g ke / ha 200 g ke / ha 400 g ke / ha 800 g ke / ha 082A2V 4.2 31.7 41.7 62.5 082B6G 0.8 27.5 36.7 62.5 082C7H 2.5 32.8 38.3 77.5 082D4F 0 33.3 36.7 70.0 082E9K 1.7 25.8 50.8 65.8 082F6B 2.5 32,5 34.2 75.8 082G3S 3.3 32,5 44,2 72.5 Ultramax 3.3 35.0 39.2 70.8 AMM-GLY3S 4.2 36.7 40.8 61.7 AMM-GLY2S 0 0.8 4.2 15.0

The effectiveness of all compositions corresponded to the effectiveness of standard compositions.

Example 76

The effect of ammonium oxalate on cationic: nonionic surfactant systems in the glyphosate ammonium salt compositions was evaluated. Compositions were obtained containing the glyphosate ammonium salt and the auxiliary ingredients shown in table 76a. The concentration of glyphosate ammonium salt in each composition was 62 g ke / l.

Table 76a Composition Component 1 wt.% Component 2 wt.% Component 3 wt.% 095A0M S69 0.73 S50 0.49 NH ₄ oxalate 0.77 095B6Y S69 0.73 S47 0.49 - - 095C4D S69 0.73 S47 0.49 NH ₄ oxalate 0.77 095D6J S70 0.73 S47 0.49 - - 095E3K S70 0.73 S47 0.49 NH ₄ oxalate 0.77 095F7B S70 0.73 S50 0.49 NH ₄ oxalate 0.77 095G1Q - - S47 1.22 - - 095H8T - - S47 1.22 NH ₄ oxalate 0.77

The compositions shown in Table 76a and the comparative compositions of Roundup UltraMax, AMM-GLY2S, and AMM-GLY3S were applied to the plants of the Theofrasta funiculus (ABUTH) and the blackberry rooster millet (ECHCF). The results, the average of all replicates of the experiments for each treatment and for each plant species, as well as the total average for all plant species are presented in tables 76b and c.

Table 76b
% Inhibition of ABUTH 19 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 095A0M 63.3 81.7 94.7 95.7 095B6Y 10 62.5 72.5 80.8 095C4D 59.2 82.5 89.2 96.0 095D6J 34.2 63.3 74,2 85.0 095E3K 60.8 86.7 94.3 97.0 095F7B 64,2 90.0 97.5 98.3 095G1Q 5.8 16.7 50.8 58.3 095H8T 1.7 61.7 77.5 83.3 AMM-GLY3S 6.7 65.0 76.7 88.3 Ultramax 9.2 62.5 75.8 86.7 Table 76c
% Inhibition of ECHCF 19 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 095A0M thirty 65.8 67.5 86.7 095B6Y 6.7 57.5 59.2 68.3 095C4D 2.5 60.0 60.8 70.0 095D6J 2.5 57.5 60.8 63.3 095E3K 45.8 58.3 74,2 85.0 095F7B 46.7 67.5 70.0 77.5 095G1Q 4.2 38.3 55.8 59.2 095H8T 1.7 55.0 58.3 65.0 AMM-GLY3S 32,5 62.5 68.3 80.8 Ultramax 2.5 60.8 66.7 70.0

The effectiveness of the cationic: nonionic surfactant system containing oxalic acid was very high for both liquid and dry compositions used to destroy the Theophrastus cordivum. The effectiveness of the composition 095C4D was slightly lower than the effectiveness of standard compositions.

Example 77

The effect of ammonium oxalate on cationic: nonionic surfactant systems in the glyphosate ammonium salt compositions was evaluated. Compositions were prepared containing the glyphosate ammonium salt and the auxiliary ingredients shown in table 77a. The concentration of glyphosate ammonium salt in each composition was 62 g ke / l.

Table 77a Composition Component 1 wt.% Component 2 wt.% Component 3 wt.% 089A4D S69 1.14 - - - - 089B8J S69 0.57 S50 0.57 - - 089C5F S69 0.57 S50 0.57 NH ₄ oxalate 0.76 089H0I S70 0.57 S50 0.57 NH ₄ oxalate 0.76 089E2N S69 0.52 S50 0.70 - - 089F7G S69 0.52 S50 0.70 NH ₄ oxalate 0.76 089I5W S70 0.52 S50 0.70 NH ₄ oxalate 0.76 089J1L S70 0.52 S50 0.70 - -

The compositions shown in Table 77a and the comparative compositions of Roundup UltraMax and AMM-GLY3S were applied to the plants of the Theofrasta teardrop (ABUTH) and the blackberry rooster millet (ECHCF). The results, the average of all replicates of the experiments for each treatment and for each plant species, as well as the total average for all plant species are presented in tables 77b and c.

Table 77b
% Inhibition of ABUTH 18 days after treatment Composition 100 g ke / ha 200 g ke / ha 400 g ke / ha 800 g ke / ha 089A4D 5 76.7 87.5 94.2 089B8J 72.3 86.7 96.5 99.8 089C5F 86.7 91.7 99.0 100.0 089H0I 86.7 93.8 99.8 100.0 089E2N 74,2 86.7 97.8 98.7 089F7G 85.0 93.3 99.8 99.8 089I5W 82.5 95.0 98.0 99.5 089J1L 71.7 88.3 98.2 99,2 AMM-GLY3S 44,2 73.3 86.7 90.0 Ultramax 33.3 79.2 93.8 96.5

The effectiveness of compositions containing NH ₄ -oxalate was higher than the effectiveness of compositions not containing ammonium oxalate. All compositions except 089A4D, which contained a cationic surfactant without the addition of a nonionic surfactant or oxalate, were more effective than standard compositions.

Table 77c
% Inhibition of ECHCF 18 days after treatment Composition 100 g ke / ha 200 g ke / ha 400 g ke / ha 800 g ke / ha 089A4D 46.7 71.7 89.2 90.0 089B8J 50,0 84.2 92.5 92.7 089C5F 66.7 83.3 93.0 94.3 089H0I 70.8 90.5 93.0 93.3 089E2N 62.5 81.7 91.7 91.7 089F7G 67.5 83.3 94.2 90.0 089I5W 61.7 80.8 93.3 95.2 089J1L 84.2 86.7 91.7 95.2 AMM-GLY3S 51.7 75.8 89.2 92.5 Ultramax 59.2 78.3 88.3 93.3

The effectiveness of compositions containing NH ₄ -oxalate was higher than the effectiveness of compositions not containing ammonium oxalate. All compositions except 089A4D, which contained a cationic surfactant without the addition of a nonionic surfactant or oxalate, were more effective than standard compositions.

Example 78

The effects of ammonium oxalate and oxalic acid on cationic: nonionic surfactant systems in the glyphosate ammonium salt compositions were evaluated. Compositions were obtained containing the ammonium salt of glyphosate and the auxiliary ingredients shown in table 78a. The concentration of glyphosate ammonium salt in each composition was 62 g ke / l.

Table 78a Composition Component 1 wt.% Component 2 wt.% Component 3 wt.% 089A3H S69 1.14 - - - - 089B9I S69 0.57 S50 0.57 - - 089C5G S69 0.57 S50 0.57 NH ₄ oxalate 0.76 089D3X S69 0.57 S50 0.57 Oxalic acid 0.76 089E7V S69 0.52 S50 0.70 - - 089F2Z S69 0.52 S50 0.70 NH ₄ oxalate 0.70 089G8M S69 0.52 S50 0.70 Oxalic acid 0.76

The compositions shown in Table 78a and the comparative compositions Roundup UltraMax and AMM-GLY3S were applied to prickly brisket plants (SIDSP). The results, the average of all replicates of the experiments for each treatment and for each plant species, as well as the total average for all plant species are presented in table 78b.

Table 78b
% SIDSP inhibition 15 days after treatment Composition 100 g ke / ha 200 g ke / ha 300 g ke / ha 400 g ke / ha 089A3H 57.5 76.7 84.2 92.2 089B9I 70.8 90.0 90.8 94.7 089C5G 70.8 87.5 90.0 92.2 089D3X 69.2 87.5 89.2 89.2 089E7V 72.5 88.3 93.0 95.7 089F2Z 74,2 86.7 89.2 93.0 089G8M 69.2 87.5 90.0 93.0 AMM-GLY2S 27.5 32,5 58.3 65.0 AMM-GLY3S 54,2 71.7 87.5 90.8 Ultramax 56.7 72.5 88.3 92.2

Example 79

The effects of acid, oxidizing agents and reducing agents in solutions of glyphosate potassium salt were evaluated. Compositions containing glyphosate were obtained as shown in table 79a, where the concentration is expressed in wt.%, Unless otherwise noted.

Table 79a Component Composition 553R2P Composition 368W2I Composition 318U8N Glyphosate IPA salt 360 g ke / l - - Glyphosate potassium salt - 31% 480 g ke / l S83 - 7.4% 7.4% S84 9.6% - - S85 6.4% - - S86 - 4.9% 4.9% S87 1,5 - - S88 1,0 - - S89 1,0 - - Octylamine 6.5% 6.5%

Aqueous compositions containing 5% potassium salt of glyphosate and the indicated oxidizing or reducing agent were obtained as shown in table 79b.

Table 79b Composition Component 1 wt.% 901A4C Oxalic acid 0.3 901B7J L-malic acid 0.3 901C0L L-5-methylglutamate 0.3 901D2B L-tartaric acid 0.3 901E7H Dithiothreitol 0.3 901F4V Dithioerythritol 0.3

The compositions shown in Tables 79a and b, and the comparative compositions of Roundup UltraMax and 725K were applied to the plants of the Theofrasta cannabis (ABUTH). The results, average for all replicates of the experiments for each treatment and for each plant species, are presented in table 79c.

Table 79c
% Inhibition of ABUTH 15 days after treatment Composition 100 g ke / ha 150 g ke / ha 200 g ke / ha 300 g ke / ha 901A4C 50.8 65.0 74,2 85.0 901B7J 8.3 22.5 63.3 70.0 901C0L 18.3 35.0 35.8 69.2 901D2B 6.7 30.8 53.3 71.7 901E7H 13.3 25.0 37.5 66.7 901F4V 26.7 28.3 55.0 74,2 553R2P 53.3 76.7 85.8 89.2 368W2I 37.5 72.5 78.3 87.5 318U8N 55.0 72.5 80.8 85.8 725K 1.7 23.3 47.5 74,2 Ultramax 28.3 68.3 80.0 87.5

The addition of each oxidizing agent or acid with the exception of dithiothreitol gave a slight increase in efficiency compared to the effectiveness of the composition containing only one salt (725K). Oxalic acid gave the highest efficiency equal to or higher than the effectiveness of Roundup UltraMax.

Compositions containing cationic: nonionic surfactant systems in combination with oxalate have higher efficacy than systems with only one surfactant and standard compositions. In general, the addition of oxalic acid in this test did not give any significant advantage in destroying the spiny brisket.

Examples 80-99

Field studies were conducted to evaluate the synergistic effect of diammonium oxalate and oxalic acid in glyphosate compositions, including cationic systems: nonionic surfactants or cationic surfactant systems. Glyphosate compositions were applied after emergence to all target weeds, if their height was usually from about 8 cm to 30 cm, depending on the type of plant and environmental conditions. The size of the cultivated plot was 2 meters wide and 4.6 meters long. The treatments were carried out using a spray boom. The spray rate ranged from about 93 to 112 l / ha. In this case, cone-shaped nozzles of a Tee-Jet fan-type sprayer were used at the appropriate pressure in the sprayer and at the appropriate frequency and height from the weed cover, as recommended in the Tee-Jet technical manual. The experimental design for each study involved the use of fractional plots with four repetitions (replicas). Each composition was usually applied at four or five application rates in each test. All compositions were applied based on the acid equivalent of glyphosate.

Traditional estimates of weed control were carried out at the time of maximum inhibition of plants with glyphosate compositions (14-35 days after treatment, or DPO). Estimates were established based on quantitative visual observations (0 = no inhibition, 100 = complete kill, 85% = threshold value for a commercial herbicide preparation). The effect of glyphosate on plant species growing in the treated plot was compared by the quality and power of plants growing in the untreated, buffer area directly surrounding the plot.

Glyphosate-containing compositions for the field tests described in examples 80-89 were obtained as indicated in the table below, where the concentration is expressed in wt.%.

Component Composition
483Y9R Composition 942G6E Composition 944R5W Composition 948U2P Glyphosate 68% ammonium glyphosate salt 68% ammonium glyphosate salt 68% ammonium glyphosate salt 31% IPA Salt Glyphosate S32 - - - 5.0% S50 7.9% - - - S69 5.7% 5.7% - - S72 - 7.9% 7.9% - S74 0.1% 0.1% 0.1% - S76 - - 5.7% - S90 - - - 1.8% di-NH ₄ oxalate 8.3% 8.3% 8.3% 3.0% Sodium sulfite 0.4% 0.4% 0.4% - Hcl - - - 0.1% Polyethylene glycol - - - 2.0% S1 - 10.0% - - S5 6.5% - - - S8 7.5% - - - S30 - - 10.0% - S61 - - - 2% S64 - - - 10.0% S91 - 1.5% 1.5% - Oxalic acid 0.8% 1.2% 1.5% 8%

Example 80

Field trials to evaluate the 770W2X composition compared to the standard Roundup UltraMax anti-ragweed (AMBTR) composition were conducted in Monmouth, PC. Illinois. The results, average for all repetitions of experiments for each treatment, are presented in the table below.

% Inhibition of AMBTR 21 days after treatment Composition 105 g ke / ha 263 g ke / ha 420 g ke / ha 578 g ke / ha 736 g ke / ha 770W2X 28.8 62.8 81.0 85.3 88.8 Ultramax 28.8 59.5 76.0 82.3 91.5

Composition 770W2X, containing the IPA salt of glyphosate, cationic surfactants and oxalic acid, had slightly better inhibition efficiency compared to UltraMax except when the highest application rate was used.

Example 81

Field trials to evaluate the effect of the 770W2X composition against common dandelion (TAROF) compared to the standard Roundup UltraMax composition were conducted in Monmouth, pc. Illinois. The results, average for all repetitions of experiments for each treatment, are presented in the table below.

% Inhibition of TAROF 24 days after treatment Composition 325 g ke / ha 585 g ke / ha 845 g ke / ha 1105 g ke / ha 1429 g ke / ha 770W2X 46.0 48.3 62.3 69.5 73.5 Ultramax 43.3 49.8 65.5 63.0 76.3

Composition 770W2X had an inhibition efficiency similar to that of the UltraMax composition at all application rates.

Example 82

Field trials to evaluate the effect of composition 770W2X against highlander bindweed (POLCO) compared to the standard Roundup UltraMax were conducted in Monmouth, PC. Illinois. The results, average for all repetitions of experiments for each treatment, are presented in the table below.

% Inhibition of POLCO 23 days after treatment Composition 263 g ke / ha 368 g ke / ha 526 g ke / ha 683 g ke / ha 770W2X 56.5 79.3 92.3 96.0 Ultramax 43.3 74.0 86.8 91.0

Composition 770W2X had a higher inhibition efficiency than the UltraMax composition at all application rates.

Example 83

Field trials to evaluate the effect of composition 770W2X against Chaff Perennial (LOLPE), Primrose (PRITR), Chaff Hard (LOLMG) and Bonfire Roofing (MALSI) compared to the standard composition Roundup UltraMax were performed in Loxley, PC. Alabama. The results, average for all replicates of experiments for each treatment and for each type of plant, are presented in the table below.

% Inhibition of LOLPE 19 days after treatment Composition 526 g ke / ha 788 g ke / ha 1051 g ke / ha 1314 g ke / ha 1577 g ke / ha 770W2X 95.8 one hundred 98.8 one hundred one hundred Ultramax 97.3 98.8 one hundred one hundred one hundred

Composition 770W2X had an inhibition efficiency similar to that of the UltraMax composition at all application rates.

% Inhibition of PRITR 19 days after treatment Composition 526 g ke / ha 788 g ke / ha 1051 g ke / ha 1314 g ke / ha 1577 g ke / ha 770W2X 75.3 81.8 86.5 94.0 93.5 Ultramax 76.3 85.0 91.7 90.5 94.8

Composition 770W2X had an inhibition efficiency similar to that of the UltraMax composition at all application rates.

% Inhibition of LOLMG 19 days after treatment Composition 526 g ke / ha 788 g ke / ha 1051 g ke / ha 1314 g ke / ha 1577 g ke / ha 770W2X 87.8 86.8 94.5 99.5 96.3 Ultramax 85.0 91.3 98.0 one hundred one hundred

Composition 770W2X had lower inhibition efficiency than the UltraMax composition at all application rates.

% Inhibition of MALSI 19 days after treatment Composition 526 g ke / ha 788 g ke / ha 1051 g ke / ha 1314 g ke / ha 1577 g ke / ha 770W2X 71.3 76.8 81.3 85.5 89.3 Ultramax 69.5 73.3 82.0 87.0 86.5

Composition 770W2X had an inhibition efficiency similar to that of the UltraMax composition at all application rates.

Example 84

Field trials to evaluate the effect of composition 770W2X against Chaff Perennial (LOLPE), Primrose (PRITR), Chaff Hard (LOLMG) and Bonfire Roofing (MALSI) compared to the standard composition Roundup UltraMax were performed in Loxley, PC. Alabama. The results, average for all replicates of experiments for each treatment and for each type of plant, are presented in the table below.

% Inhibition of LOLPE 18 days after treatment Composition 390 g ke / ha 585 g ke / ha 780 g ke / ha 975 g ke / ha 1170 g ke / ha 770W2X 81.5 98.8 95.0 one hundred one hundred Ultramax 87.8 98.8 95.5 one hundred 97.5

Composition 770W2X had an inhibition efficiency similar to that of UltraMax at all application rates except the lowest application rates.

% PRITR inhibition 18 days after treatment Composition 390 g ke / ha 585 g ke / ha 780 g ke / ha 975 g ke / ha 1170 g ke / ha 770W2X 70.8 82.0 84.3 87.5 91.3 Ultramax 74.3 81.0 84.3 90.3 91.5

Composition 770W2X had an inhibition efficiency similar to that of the UltraMax composition at all application rates.

% Inhibition of LOLMG 18 days after treatment Composition 390 g ke / ha 585 g ke / ha 780 g ke / ha 975 g ke / ha 1170 g ke / ha 770W2X 75.0 85.0 86.5 89.0 95.0 Ultramax 80.0 83.8 86.3 94.8 95.8

Composition 770W2X had a slightly lower inhibition efficiency than the UltraMax composition at all application rates.

% Inhibition of MALSI 18 days after treatment Composition 390 g ke / ha 585 g ke / ha 780 g ke / ha 975 g ke / ha 1170 g ke / ha 770W2X 72.5 80.3 79.0 85.8 88.3 Ultramax 74.3 73.5 80.7 80.0 84.3

Composition 770W2X had a higher inhibition efficiency than the UltraMax composition at all application rates.

Example 85

Field trials to evaluate the effect of the 770W2X composition against round saturation (CYPRO) compared to the standard Roundup UltraMax composition were performed in Loxley, pc. Alabama. The results, average for all repetitions of experiments for each treatment, are presented in the table below.

% CYPRO Inhibition 22 days after treatment Composition 1500 g ke / ha 1750 g ke / ha 2000 g ke / ha 2250 g ke / ha 2500 g ke / ha 770W2X 80.5 77.5 83.5 85.0 93.5 Ultramax 77.0 80.8 80.8 85.5 89.3

Composition 770W2X had a slightly higher inhibition efficiency than the UltraMax composition at all application rates except the lowest application rates.

Example 86

Field trials to evaluate the effect of the 770W2X composition against the tinea Theofrast (ABUTH), sickle-astragalus (CASOB), hemp sowing (SEBEX), narrow-leaved morning glory (IPOLA), amaranth (AMASS) and spiny brisket (SIDSP) compared with the standard composition Roundup UltraMax in Loxley Alabama. The results, average for all replicates of experiments for each treatment and for each type of plant, are presented in the table below.

% Inhibition of ABUTH 23 days after treatment Composition 210 g ke / ha 420 g ke / ha 631 g ke / ha 840 g ke / ha 1051 g ke / ha 770W2X 49.0 70.3 93.0 96.0 one hundred Ultramax 47.0 64.5 76.0 84.0 94.8

Composition 770W2X had a higher inhibition efficiency than the UltraMax composition at all application rates.

% Inhibition of CASOB 23 days after treatment Composition 210 g ke / ha 420 g ke / ha 631 g ke / ha 840 g ke / ha 1051 g ke / ha 770W2X 46.3 67.5 87.0 93.0 95.0 Ultramax 54.5 63.3 76.3 78.5 93.5

Composition 770W2X had a slightly higher inhibition efficiency compared to the effectiveness of the UltraMax composition at all application rates except the lowest application rates.

% Inhibition of SEBEX 23 days after treatment Composition 210 g ke / ha 420 g ke / ha 631 g ke / ha 840 g ke / ha 1051 g ke / ha 770W2X 43.8 64.0 81.8 79.0 92.8 Ultramax 45.0 58.8 72.0 68.5 97.0

Composition 770W2X had a slightly higher inhibition efficiency compared to the effectiveness of the UltraMax composition at all application rates except the lowest application rates.

% IPOLA Inhibition 23 days after treatment Composition 210 g ke / ha 420 g ke / ha 631 g ke / ha 840 g ke / ha 1051 g ke / ha 770W2X 47.5 63.3 70.5 71.8 81.5 Ultramax 45.0 59.0 66.5 67.5 79.8

Composition 770W2X had a slightly higher inhibition efficiency compared to UltraMax at all application rates.

% Inhibition of AMASS 23 days after treatment Composition 210 g ke / ha 420 g ke / ha 631 g ke / ha 840 g ke / ha 1051 g ke / ha 770W2X 85.0 96.0 98.0 97.0 99.0 Ultramax 90.8 91.3 98.0 94.5 98.0

Composition 770W2X had a slightly higher inhibition efficiency compared to the effectiveness of the UltraMax composition at all application rates except the lowest application rates.

% Inhibition of SIDSP 23 days after treatment Composition 210 g ke / ha 420 g ke / ha 631 g ke / ha 840 g ke / ha 1051 g ke / ha 770W2X 86.0 93.0 96.8 99.3 99.0 Ultramax 85.0 87.3 95.0 94.8 99.5

Composition 770W2X had a slightly higher inhibition efficiency than the UltraMax composition at all application rates.

Example 87

Field trials to evaluate the effect of the 770W2X composition against the shepherd’s bag (CAPBP) compared to the standard Roundup UltraMax composition were performed in Stoneville, PC. Mississippi. The results, average for all repetitions of experiments for each treatment, are presented in the table below.

% Inhibition of CAPBP 21 days after treatment Composition 260 g ke / ha 390 g ke / ha 520 g ke / ha 650 g ke / ha 780 g ke / ha 770W2X 68.8 82.5 80.0 88.8 92.5 Ultramax 63.8 85.0 85.0 85.0 90.0

Composition 770W2X had an inhibition efficiency similar to that of the UltraMax composition at all application rates.

Example 88

Field trials to evaluate the effect of the 770W2X composition against the morning glory narrow-leaved (IPOSS) compared to the standard Roundup UltraMax composition were carried out in Stoneville, PC. Mississippi. The results, average for all repetitions of experiments for each treatment, are presented in the table below.

% IPOLA Inhibition 22 days after treatment Composition 325 g ke / ha 455 g ke / ha 585 g ke / ha 715 g ke / ha 845 g ke / ha 770W2X 67.5 68.8 77.5 87.5 88.8 Ultramax 63.8 67.5 73.8 82.5 83.8

Composition 770W2X had a slightly higher inhibition efficiency than the UltraMax composition at all application rates.

Example 89

Field trials to evaluate the effect of compositions 483Y9R and 769R5V against porcine fingernail (CYNDA) compared to the standard composition AMM-GLY3S were performed in Pergamino, Argentina. The results, average for all repetitions of experiments for each treatment, are presented in the table below.

% CYNDA Inhibition 14 Days After Treatment Composition 720 g ke / ha 1080 g ke / ha 1440 g ke / ha 1800 g ke / ha 483Y9R 43.8 52,5 68.5 76.3 769R5V 31.3 55.0 67.5 80.0 AMM-GLY3S 28.8 45.0 51.3 63.8

Compositions 483Y9R and 769R5V, containing cationogenic: nonionic surfactant systems and ammonium oxalate or oxalic acid, had significantly higher inhibition efficacy than AMM-GLY3S at all application rates. Compositions 483Y9R and 769R5V gave a similar effect at all application rates.

Example 90

Field trials to evaluate the effects of compositions 483Y9R and 769R5V against white clover (MEUSS) compared to the standard composition AMM-GLY3S were performed in Pergamino, Argentina. The results, average for all repetitions of experiments for each treatment, are presented in the table below.

% Inhibition of MEUSS 17 days after treatment Composition 1080 g ke / ha 1440 g ke / ha 1880 g ke / ha 483Y9R 43.3 55.0 71.3 769R5V 33.8 50,0 48.3 AMM-GLY3S 35.0 55.0 65

Composition 483Y9R had a higher inhibition efficiency than the composition AMM-GLY3S at all application rates. Composition 769R5V was less effective than composition 483Y9R and standard composition AMM-GLY3S.

Example 91

Field trials to evaluate the effects of compositions 483Y9R and 769R5V against amaranth (AMAQU) compared to the standard composition AMM-GLY3S were performed in Aljo Ledesma, Argentina. The results, average for all repetitions of experiments for each treatment, are presented in the table below.

% AMAQU inhibition 14 days after treatment Composition 748 g ke / ha 960 g ke / ha 1156 g ke / ha 1564 g ke / ha 483Y9R 46.7 73.8 75.0 88.8 769R5V 25.0 53.8 68.8 81.3 AMM-GLY3S 33.3 68.8 75.0 80.0

Composition 483Y9R had a higher inhibition efficiency than the composition AMM-GLY3S at all application rates. Composition 769R5V was less effective than composition 483Y9R and standard composition AMM-GLY3S.

Example 92

Field trials to evaluate the effect of composition 483Y9R against comelina (COMSS) compared to the standard composition AMM-GLY3S were performed in Pergamino, Argentina. The results, average for all repetitions of experiments for each treatment, are presented in the table below.

% COMSS Inhibition 17 Days After Treatment Composition 2160 g ke / ha 2640 g ke / ha 2880 g ke / ha 483Y9R 70.0 70.0 73.8 AMM-GLY3S 67.5 74.5 73.0

Composition 483Y9R had an inhibition efficiency similar to that of the AMM-GLY3S composition at all application rates.

% COMSS inhibition 28 days after treatment Composition 2160 g ke / ha 2640 g ke / ha 2880 g ke / ha 483Y9R 81.3 85.3 89.8 AMM-GLY3S 80.0 85.0 86.0

Composition 483Y9R had a slightly higher inhibition efficiency than AMM-GLY3S at all application rates.

Example 93

Field trials to evaluate the efficacy of 942G6E, 944R5W, and 948U2P against the clumsy (LAMAM) compared to the standard 540KS were performed in Fredericksburg, Texas. The results, average for all repetitions of experiments for each treatment, are presented in the table below.

% Inhibition of LAMAM 23 days after treatment Composition 315 g ke / ha 473 g ke / ha 631 g ke / ha 788 g ke / ha 946 g ke / ha 942G6E 60.8 74.0 72.5 69.5 76.3 944R5W 66.5 72.5 71.3 74.5 74.5 948U2P 67.5 63.0 66.8 74.3 79.8 540KS 65.5 61.8 72.8 69.8 74.3

Compositions 942G6E, 944R5W and 948U2P, each of which contained glyphosate and a system of cationic: nonionic surfactants, had a slightly higher inhibition efficiency than composition 540KS at all application rates.

Example 94

Field trials to evaluate the efficacy of 942G6E, 944R5W, and 948U2P against the clumsy (LAMAM) compared to the standard 540KS were performed in Thrall, Texas. The results, average for all repetitions of experiments for each treatment, are presented in the table below.

% Inhibition of LAMAM 22 days after treatment Composition 315 g ke / ha 473 g ke / ha 631 g ke / ha 788 g ke / ha 946 g ke / ha 942G6E 70.3 79.0 76.5 - 88.3 944R5W 76.0 75.8 72.5 84.3 87.5 948U2P 73.0 77.5 77.5 85.0 91.5 540KS 70.0 74.0 72.8 83.5 88.8

Compositions 942G6E, 944R5W and 948U2P, each of which contained glyphosate and a system of cationic: nonionic surfactants, showed a slightly higher inhibition efficiency than composition 540KS at all application rates.

Example 95

Field trials to evaluate the effects of the 760Q3N and 761W0M compositions against the Theofrast cable rope (ABUTH) compared to the standard Roundup UltraMax composition were performed in Monmouth, pc. Illinois. The results, average for all repetitions of experiments for each treatment, are presented in the table below.

% Inhibition of ABUTH 23 days after treatment Composition 210 g ke / ha 368 g ke / ha 526 g ke / ha 683 g ke / ha 840 g ke / ha 760Q3N 58.8 77.8 84.5 88.5 98.8 761W0M 54.0 70.0 83.0 88.5 96.3 Ultramax 43.3 67.0 81.5 87.5 89.5

Compositions 760Q3N and 761W0M, each of which contained glyphosate, a cationic surfactant, and oxalic acid, had slightly higher inhibition efficiency than the UltraMax composition at all application rates.

Example 96

Field trials to evaluate the effects of the 760Q3N and 761W0M compositions against the Theofrast cable rope (ABUTH) compared to the standard Roundup UltraMax composition were performed in Monmouth, pc. Illinois. The results, average for all repetitions of experiments for each treatment, are presented in the table below.

% Inhibition of ABUTH 21 days after treatment Composition 158 g ke / ha 263 g ke / ha 420 g ke / ha 578 g ke / ha 736 g ke / ha 760Q3N 40,0 70.8 85.0 91.8 95.5 761W0M 44.5 73.8 85.3 89.3 92.5 Ultramax 33.3 64.8 82.8 85.3 90.0

Compositions 760Q3N and 761W0M, each of which contained glyphosate, a cationic surfactant, and oxalic acid, had slightly higher inhibition efficiency than the UltraMax composition at all application rates.

Example 97

Field trials for evaluating the effect of the 760Q3N and 761W0M compositions against the theotrope Theofrast (ABUTH), hemp sowing (SEBEX), narrow-leaved morning glory (IPOLA), sternum brisket (SIDSP) and sickle-like astragalus (CASOB) compared to the standard Roundup UltraMax composition PC. Alabama. The results, average for all repetitions of experiments for each treatment, are presented in the table below.

% Inhibition of ABUTH 21 days after treatment Composition 420 g ke / ha 631 g ke / ha 840 g ke / ha 1051 g ke / ha 1261 g ke / ha 760Q3N 97.3 98.3 one hundred 99.5 one hundred 761W0M 98.0 one hundred one hundred 99.5 one hundred Ultramax 94.8 one hundred one hundred 99.8 98.0

Compositions 760Q3N and 761W0M had an inhibition efficiency similar to that of UltraMax at all application rates.

% Inhibition of SEBEX 21 days after treatment Composition 420 g ke / ha 631 g ke / ha 840 g ke / ha 1051 g ke / ha 1261 g ke / ha 760Q3N 63.0 73.8 80.0 83.0 86.8 761W0M 62.5 77.8 78.0 82.8 86.3 Ultramax 62.5 74.5 83.5 86.8 91.5

Compositions 760Q3N and 761W0M had slightly lower inhibition efficiency than the UltraMax composition at all application rates.

% IPOLA Inhibition 21 days after treatment Composition 420 g ke / ha 631 g ke / ha 840 g ke / ha 1051 g ke / ha 1261 g ke / ha 760Q3N 47.0 58.8 62.5 78.8 70.5 761W0M 46.3 58.8 67.0 75.8 72.5 Ultramax 47.0 57.0 61.3 75.3 74.3

Compositions 760Q3N and 761W0M had a slightly higher inhibition efficiency than the UltraMax composition at all application rates.

% SIDSP inhibition 21 days after treatment Composition 420 g ke / ha 631 g ke / ha 840 g ke / ha 1051 g ke / ha 1261 g ke / ha 760Q3N 88.8 95.8 98.0 99.0 98.0 761W0M 90.0 94.8 99.0 98.0 94.8 Ultramax 82.8 93.3 93.0 98.0 98.0

Compositions 760Q3N and 761W0M had a higher inhibition efficiency than the UltraMax composition at all application rates.

% Inhibition of CASOB 21 days after treatment Composition 420 g ke / ha 631 g ke / ha 840 g ke / ha 1051 g ke / ha 1261 g ke / ha 760Q3N 87.3 87.0 87.3 87.8 87.8 761W0M 88.5 88.5 87.3 88.0 87.3 Ultramax 86.8 87.3 87.3 89.0 87.3

Compositions 760Q3N and 761W0M had an inhibition efficiency similar to that of UltraMax at all application rates.

Example 98

Field trials to evaluate the effects of formulations 760Q3N and 761W0M against the Tailworm Theophrastus (ABUTH), hemp sowing (SEBEX), narrow-leaved morning glory (IPOLA) and sickle-astragalus (CASOB) compared to the standard Roundup UltraMax composition were performed in Stoneville, pc. Mississippi. The results, average for all repetitions of experiments for each treatment, are presented in the table below.

% Inhibition of ABUTH 21 days after treatment Composition 390 g ke / ha 520 g ke / ha 650 g ke / ha 780 g ke / ha 910 g ke / ha 760Q3N 81.3 86.3 87.5 87.5 93.8 761W0M 78.8 81.3 87.5 86.3 93.8 Ultramax 65.0 71.3 72.5 86.3 88.8

Compositions 760Q3N and 761W0M had significantly higher inhibition efficiency than the UltraMax composition at all application rates. Composition 760Q3N had a slightly higher efficiency than composition 761W0M at all application rates.

% Inhibition of SEBEX 21 days after treatment Composition 390 g ke / ha 520 g ke / ha 650 g ke / ha 780 g ke / ha 910 g ke / ha 760Q3N 51.3 53.8 65.0 67.5 73.8 761W0M 55.0 66.3 66.3 68.8 76.3 Ultramax 58.8 53.8 68.8 77.5 81.3

Compositions 760Q3N and 761W0M had lower inhibition efficiency than the UltraMax composition at all application rates. Composition 761W0M had a slightly higher efficiency than composition 760Q3N, for all application rates.

% IPOLA Inhibition 21 days after treatment Composition 390 g ke / ha 520 g ke / ha 650 g ke / ha 780 g ke / ha 910 g ke / ha 760Q3N 62.5 72.5 75.0 72.5 82.5 761W0M 58.8 72.5 75.0 71.3 86.3 Ultramax 48.8 66.3 70.0 72.5 80.0

Compositions 760Q3N and 761W0M had increased inhibition efficiency compared to UltraMax at all application rates. Compositions 761W0M and 760Q3N had similar efficacy.

% Inhibition of CASOB 21 days after treatment Composition 390 g ke / ha 520 g ke / ha 650 g ke / ha 780 g ke / ha 910 g ke / ha 760Q3N 76.3 75.0 83.8 81.3 87.5 761W0M 72.5 81.3 83.8 82.5 90.0 Ultramax 73.8 70.0 81.3 82.5 86.3

Compositions 760Q3N and 761W0M had increased inhibition efficiency compared to UltraMax at all application rates. Compositions 761W0M and 760Q3N had similar efficacy.

Example 99

Field trials to evaluate the effect of the 769R5V composition against avian highlander (POLAV) compared to the standard composition AMM-GLY3S were carried out in Fontainsuel, Argentina. The results, average for all repetitions of experiments for each treatment, are presented in the table below.

% POLAV Inhibition 22 Days After Treatment Composition 630 g ke / ha 945 g ke / ha 1260 g ke / ha 769R5V 25.0 35.0 48.8 AMM-GLY3S 17.5 25.0 40,0

Composition 769R5V had a significantly higher inhibition efficiency than AMM-GLY3S at all application rates.

The present invention is not limited to the above embodiments, and may have various modifications. The above description of preferred embodiments of the invention is presented only to familiarize specialists with its ideas and practical applications, so that any specialist can use the present invention in its many forms and best adapt this invention for specific practical applications.

As for the words “include” or “contain”, “includes” or “contains”, “including” or “comprising” used in the present description (as well as in the following claims), in this regard, the applicants note that in the context descriptions of the invention, these words, unless otherwise indicated, are used in their main meaning and should be interpreted as “inclusive”, and not “exclusively”, and in the entire description of the invention the applicants put such a meaning in these words.

Claims (21)

1. An aqueous composition of a herbicidal concentrate containing: glyphosate or a salt thereof, dissolved in an aqueous medium where said glyphosate is present in a concentration that is biologically effective when the composition is diluted in a suitable volume of water to form a mixture for application of enhanced action, and applying this mixture to leaves sensitive to the herbicide (susceptible to its action) plants; a surfactant component in solution or in the form of a stable suspension, emulsion or dispersion in said medium containing one or more surfactants; and oxalic acid or its salt, upon application of which plant growth is suppressed to a greater extent than a plant treated with a standard application mixture not containing oxalic acid or its salt, but otherwise having the same composition as the specified mixture for applying enhanced action , where the specified surface-active component and oxalic acid or its salt are present in a mass ratio of 5: 1 to 40: 1, where glyphosate or its salt in acid equivalent and oxalic acid or its salt are present in a mass ratio of from about 2: 1 to 125: 1, and where the surfactant component includes one or more surfactants selected from the group consisting of: (a) aminated alkoxylated alcohols having the formula

where R ¹ represents a linear or branched alkyl containing from about 8 to about 25 carbon atoms; R ² in each of the (R ² O) _x groups independently is C ₂ -C ₄ alkylene; R ³ represents a linear or branched alkylene containing from 1 to about 6 carbon atoms; R ⁴ and R ⁵ independently represent hydrogen, hydroxyethyl, linear or branched alkyl containing from 1 to about 6 carbon atoms, and x is an average of from 1 to about 30; (b) secondary or tertiary amines having the formula

where R ¹ represents a linear or branched alkyl containing from about 8 to 20 carbon atoms, R ² and R ³ independently represent hydrogen or alkyl containing from 1 to about 6 carbon atoms; (c) monoalkoxylated amines having the formula

where R ¹ represents a linear or branched alkyl containing from 8 to 22 carbon atoms, R ² in each of the (R ² O) _x groups independently represents C ₂ -C ₄ alkylene; R is hydrogen, R ⁴ is methyl, and x is an average of 5 to 13; (d) dialkoxylated quaternary ammonium salts of the formula

where R ¹ represents a linear or branched alkyl containing from 8 to 22 carbon atoms, R ² in each of the (R ² O) _x and (R ² O) _y groups independently represents C ₂ -C ₄ alkylene; R ³ represents hydrogen, R ⁴ represents hydrogen or linear or branched alkyl containing from 1 to 6 carbon atoms, the sum of x and y is equal to the average number from 2 to 20, and X ^- is an agriculturally acceptable anion; (e) quaternary ammonium salts of the formula

where R ¹ represents a linear or branched alkyl containing from 4 to 16 carbon atoms, R ² , R ³ and R ⁴ independently represents a linear or branched alkyl containing from 1 to 6 carbon atoms, and X ^- represents an agriculturally acceptable anion ; (f) amino esters of the formula:

where R ¹ represents a linear or branched alkyl containing from 8 to 22 carbon atoms, R ² represents a linear or branched alkyl containing from 2 to 6 carbon atoms, R ³ and R ⁴ independently represent hydrogen or (R ⁵ O) _x R ⁶ , where R ⁵ in each of the - (R ⁵ O) _x groups independently is C ₂ -C ₄ alkylene, R ⁶ is hydrogen, and x is an average of 1 to 30; (g) diamines of the formula:

where R ¹ represents a linear or branched alkyl containing from 8 to 22 carbon atoms, R ⁴ represents hydrogen, a linear or branched alkyl containing from 1 to 6 carbon atoms, or - (R ⁶ O) _m H, R ³ and R ⁵ represent hydrogen or linear or branched alkyl containing from 1 to 6 carbon atoms, R ² and R ⁸ independently represent alkylene containing from 2 to 6 carbon atoms, R ⁶ in each of the (R ⁶ O) _m groups independently represents C ₂ -C ₄ alkylene, X represents -C (O) -, m is an average of 1 to 20, z is 0 or 1, and n, y equal to 0; (h) dialkoxylated amines having the formula:

where R ¹ represents a linear or branched alkyl containing from 8 to 22 carbon atoms, R ² in each of the (R ² O) _x and (R ² O) _y groups independently represents C ₂ -C ₄ alkylene, R ³ represents hydrogen itself, and x and y are independently equal to the average number from 1 to 20; (i) alkoxylated alcohols having the formula

where R ¹ represents a linear or branched alkyl containing from 8 to 30 carbon atoms, R ² in each (R ² O) _x group independently represents C ₂ -C ₄ alkylene, R ³ represents hydrogen, and x is equal to the average number from 5 to 40; (j) glycosides of the formula

where n denotes a degree of polymerization of from 1 to 5, or the number of glycosidic groups, and R is a branched or straight chain alkyl, preferably containing from 4 to 18 carbon atoms, or a mixture of alkyl groups having an average length within the specified range; (k) polysiloxanes of the formula

where R ¹ represents —C _n H _2n O (CH ₂ CH ₂ O) _m (CH ₂ CH (CH ₃ ) O) _g X, n is 0-4 and is equal to a number from 0 to 30, b is equal to a number from 0 to 10, m is a number from 4 to 15, q is a number from 0 to 4, X is hydrogen, methyl or PO ₃ H ₂ , and R ₂ , R ₃ , R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₉ , R ₁₀ groups are methyl; and (1) phosphoric acid esters of the formula

where R ¹ represents a linear or branched alkyl containing from 8 to 20 carbon atoms, R ² in each of the (R ₂ O) _m groups independently represents C ₂ -C ₄ alkylene, and m is a number from 1 to 10. 2. The composition according to claim 1, where the specified oxalic acid includes an alkali metal salt of oxalic acid. 3. The composition according to claim 1, where the specified glyphosate is present mainly in the form of its potassium, monoammonium, diammonium or isopropylamine salt. 4. The composition according to claim 3, where the specified glyphosate is present mainly in the form of its potassium, monoammonium or diammonium salt. 5. The composition according to claim 1, where the mass ratio of the acid equivalent of glyphosate to surfactant is between 6: 1 to 2: 1. 6. The composition according to claim 1, where the surface-active component and oxalic acid or its salt are present in a weight ratio between 5: 1 to 20: 1. 7. The composition according to claim 1, where the concentration of the specified glyphosate exceeds 400 grams of acid equivalent (ke) glyphosate per liter. 8. The composition according to claim 7, where the concentration of the specified glyphosate exceeds 500 grams of acid equivalent (ke) glyphosate per liter. 9. The composition of claim 8, wherein the concentration of said glyphosate exceeds 540 grams of acid equivalent (ke) of glyphosate per liter. 10. A method of reducing the surface-active component in an aqueous composition of a herbicidal concentrate necessary to provide a given degree of growth inhibition, comprising diluting the composition of claim 1 with water and applying the diluted composition to plant leaves. 11. The method according to claim 10, where the specified mass ratio of the acid equivalent of glyphosate to the specified oxalic acid or its salt is between 2: 1 to 50: 1. 12. A method of inhibiting the growth of morning glory, comprising applying the aqueous composition according to claim 1 to the leaves of said morning glory. 13. The method of claim 12, wherein said weight ratio of the acid equivalent of glyphosate to said oxalic acid or its salt is between 3: 1 to 30: 1. 14. An aqueous composition of a herbicidal concentrate containing: glyphosate or a salt thereof, dissolved in an aqueous medium where said glyphosate is present in a concentration that is biologically effective when the composition is diluted in a suitable volume of water, with the formation of a mixture for applying enhanced action, and applying this mixture to the leaves of a susceptible plant; a surfactant component in the form of a solution or a stable suspension, emulsion or dispersion in said medium containing one or more cationic surfactants and one or more nonionic surfactants; and oxalic acid or its salt, upon application of which plant growth is suppressed to a greater extent than a plant treated with a standard mixture for applying the specified oxalic acid and its salt compounds, but otherwise having the same composition as the specified mixture for applying enhanced actions, where the specified surface-active component and the specified oxalic acid or its salt are present in a molar ratio of from 2: 1 to 50: 1, and where glyphosate or its salt in acid equivalent and oxalic acid or its salt are present in a mass ratio of from 2: 1 to 125: 1, and where the cationic surfactant component includes one or more surfactants selected from the group consisting of: (a) aminated alkoxylated alcohols having the formula

where R ¹ represents a linear or branched alkyl containing from 8 to 25 carbon atoms; R ² in each of the (R ² O) _x groups independently is C ₂ -C ₄ alkylene; R ³ represents a linear or branched alkylene containing from 1 to 6 carbon atoms; R ⁴ and R ⁵ independently represent hydrogen, hydroxyethyl, linear or branched alkyl containing from 1 to 6 carbon atoms, and x is equal to the average number from 1 to 30; (b) diamines of the formula

where R ¹ represents a linear or branched alkyl containing from 8 to 22 carbon atoms, R ⁴ represents hydrogen, a linear or branched alkyl containing from 1 to 6 carbon atoms, or - (R ⁶ O) _m H, R ³ and R ⁵ represent hydrogen or linear or branched alkyl containing from 1 to 6 carbon atoms, R ² and R ⁸ independently represent alkylene containing from 2 to 6 carbon atoms, R ⁶ in each of the (R ⁶ O) _m groups independently represents C ₂ -C ₄ alkylene, X represents -C (O) -, m is an average of 1 to 20, z is 0 or 1, and n, y equal to 0; (c) monoalkoxylated amines having the formula

where R ¹ represents a linear or branched alkyl containing from 8 to 22 carbon atoms, R ² in each of the (R ² O) _x groups independently represents C ₂ -C ₄ alkylene; R ³ is hydrogen, R ⁴ is methyl, and x is an average of 5 to 13; (d) quaternary ammonium salts of the formula

where R ¹ represents a linear or branched alkyl containing from 4 to 16 carbon atoms, R ² , R ³ and R ⁴ independently represents a linear or branched alkyl containing from 1 to 6 carbon atoms, and X ^- represents an agriculturally acceptable anion ; (e) dialkoxylated amines of the formula

where R ¹ represents a linear or branched alkyl containing from 8 to 22 carbon atoms, R in each of the (R ² O) _x and (R ² O) _y groups independently represents C ₂ -C ₄ alkylene, R represents hydrogen , and x and y are independently equal to the average of 1 to 20; and where the non-ionic surfactant component includes one or more surfactants selected from the group consisting of: (f) alkoxylated alcohols of the formula

where R ¹ represents a linear or branched alkyl containing from 8 to 30 carbon atoms, R ² in each (R ² O) _x group independently represents C ₂ -C ₄ alkylene, R ³ represents hydrogen, and x is equal to the average number from 5 to 40; (g) glycosides of the formula

where n denotes a degree of polymerization of from 1 to about 5, or the number of glycoside groups, and R represents a branched or straight chain alkyl, preferably containing from 4 to about 18 carbon atoms, or a mixture of alkyl groups having an average length within the specified range. 15. The composition of claim 14, wherein said glyphosate is present predominantly in the form of its potassium, mono-ammonium, diammonium or isopropylamine salt. 16. The composition according to clause 15, where the specified glyphosate is present mainly in the form of its potassium, monoammonium or diammonium salt. 17. The composition according to 14, where the specified surface-active component and the specified oxalic acid or its salt are present in a mass ratio of about 3: 1 to 50: 1. 18. The composition according to 14, where the specified concentration of glyphosate exceeds 400 grams of the acid equivalent of glyphosate per liter. 19. The composition according to p. 18, where the specified concentration of glyphosate exceeds 500 grams of acid equivalent of glyphosate per liter. 20. The composition according to claim 19, where the specified concentration of glyphosate exceeds 540 grams of the acid equivalent of glyphosate per liter. 21. A solid composition of a herbicidal concentrate containing: glyphosate ammonium salt, present in a concentration that is biologically effective when the composition is diluted in a suitable volume of water, with the formation of a mixture for applying enhanced action, and applying this mixture to the leaves of a susceptible plant; and oxalic acid or its salt, upon application of which plant growth is suppressed to a greater extent than a plant treated with a standard application mixture not containing said oxalic acid and its salt, but otherwise having the same composition as the specified application mixture enhanced action, or a surfactant component that includes one or more surfactants selected from the group consisting of: (a) aminated alkoxylated alcohols having the formula

where R ¹ represents a linear or branched alkyl containing from 8 to 25 carbon atoms; R ² in each of the (R ² O) _x groups independently is C ₂ -C ₄ alkylene; R ³ represents a linear or branched alkylene containing from 1 to 6 carbon atoms; R ⁴ and R ⁵ independently represent hydrogen, hydroxyethyl, linear or branched alkyl containing from 1 to 6 carbon atoms, and x is equal to the average number from 1 to 30; (b) diamines of the formula

where R ¹ represents a linear or branched alkyl containing from 8 to 22 carbon atoms, R ⁴ represents hydrogen, a linear or branched alkyl having from 1 to 6 carbon atoms, R ³ and R ⁵ are hydrogen or linear or branched alkyl containing from 1 to 6 carbon atoms, R ² and R ⁸ independently are alkylene containing from 2 to 6 carbon atoms, R ⁶ in each of (R ⁶ O) _m groups independently represents C ₂ -C ₄ alkylene, X represents -C (O) -, m is an average of 1 to 20, z is 0 or 1, and n, y are 0; (c) dialkoxylated amines of the formula:

where R ¹ represents a linear or branched alkyl containing from 8 to 22 carbon atoms, R ² in each of the (R ² O) _x and (R ² O) _y groups independently represents C ₂ -C ₄ alkylene, R represents hydrogen, and x and y are independently equal to an average of 1 to 20; and (d) alkoxylated alcohols of the formula

where R ¹ represents a linear or branched alkyl containing from 8 to 30 carbon atoms, R ² in each of the (R ² O) _x groups independently represents C ₂ -C ₄ alkylene, R ³ represents hydrogen, and x is equal to the average a number from 5 to 40; where the mass ratio of the acid equivalent of glyphosate to the specified oxalic acid or its salt is between 2: 1 to 100: 1 and the mass ratio of the surfactant to oxalic acid or its salt is between 1: 1 to 20: 1.