Aqueous Adjuvant Composition For Increasing The Efficacy Of Electrolyte Active Substances

Abstract

An adjuvant composition containing a) one or more alkyl glucamides of the formula (I), wherein R1 represents a linear or branched alkyl group having 5 to 9 carbon atoms, R2 represents an alkyl group having 1 to 3 carbon atoms; b) at least one water-soluble ammonium salt, preferably selected from the group consisting of ammonium sulfate, ammonium nitrate, ammonium nitrate urea, ammonium phosphate, ammoniumeitrate, ammonium chloride, and ammonium thiosulfate; c) propylene glycol, dipropylene glycol, mixtures of propylene glycol and dipropylene glycol, in each case optionally in a mixture with polypropylene glycol and/or polyethylene glycol, in each case with up to 10 repeating units; and d) water is suitable for increasing the efficacy of electrolyte active substances.

##STR00001##

Claims

1. An adjuvant composition comprising a) at least one alkylglucamide of the formula (I) ##STR00005## in which R1 is a linear or branched alkyl group having 5 to 9 carbon atoms, R2 is an alkyl group having 1 to 3 carbon atoms, b) at least one water-soluble ammonium salt, c) propylene glycol, dipropylene glycol, mixtures of propylene glycol and dipropylene glycol, each optionally in a mixture with polypropylene glycol and/or polyethylene glycol, each having up to ten repeat units, and d) water.

2. The adjuvant composition as claimed in claim 1, wherein R1 is a linear or branched alkyl group having 7 to 9 carbon atoms and R2 is a methyl group.

3. The adjuvant composition as claimed in claim 1, which is a mixture of octyl-N-methylglucamide R.sup.1C.sub.7-alkyl and decyl-N-methylglucamide RC.sub.9-alkyl or nonyl-N-methylglucamide, R.sup.1C.sub.8-alkyl.

4. The adjuvant composition as claimed in claim 1, wherein the proportion of the at least one alkylglucamide a) is 10% to 90% by weight, based on the total weight of the composition.

5. The adjuvant composition as claimed in claim 1, wherein the ammonium salt b) is selected from the group consisting of ammonium sulfate, ammonium nitrate, ammonium nitrate urea, ammonium phosphate, ammonium citrate, ammonium chloride and ammonium thiosulfate.

6. The adjuvant composition as claimed in claim 1, wherein component c) is propylene glycol.

7. A method for enhancing the biological activity of pesticides, comprising the step of adding at least one adjuvant composition comprising a) at least one alkylglucamide of the formula (I) ##STR00006## in which R1 is a linear or branched alkyl group having 5 to 9 carbon atoms, R2 is an alkyl group having 1 to 3 carbon atoms, b) at least one water-soluble ammonium salt, c) propylene glycol, dipropylene glycol, mixtures of propylene glycol and dipropylene glycol, each optionally in a mixture with polypropylene glycol and/or polyethylene glycol, each having up to ten repeat units, and d) water to the pesticide.

8. A method for producing an aqueous pesticide composition comprising the step of adding at least one adjuvant composition comprising a) at least one alkylglucamide of the formula (I) ##STR00007## in which R1 is a linear or branched alkyl group having 5 to 9 carbon atoms, R2 is an alkyl group having 1 to 3 carbon atoms, b) at least one water-soluble ammonium salt, c) propylene glycol, dipropylene glycol, mixtures of propylene glycol and dipropylene glycol, each optionally in a mixture with polypropylene glycol and/or polyethylene glycol, each having up to ten repeat units, and d) water to the aqueous pesticide composition.

9. A pesticide composition comprising a) at least one alkylglucamide of the formula (I) ##STR00008## in which R1 is a linear or branched alkyl group having 5 to 9 carbon atoms, R2 is an alkyl group having 1 to 3 carbon atoms, b) at least one ammonium salt, c) propylene glycol, dipropylene glycol, mixtures of propylene glycol and dipropylene glycol, each optionally in a mixture with polypropylene glycol and/or polyethylene glycol, each having up to ten repeat units, d) water, e) optionally at least one cosolvent, f) optionally at least one auxiliary, g) at least one water-soluble pesticide, h) optionally at least one water-insoluble pesticide.

10. The pesticide composition as claimed in claim 9, wherein the one or more water-soluble pesticide(s) of component g) are selected from the group consisting of herbicides.

11. The pesticide composition as claimed in claim 9, wherein the at least one water-soluble pesticide of component g) is selected from the group consisting of water-soluble salts of 2,4-D, bentazon, dicamba, fomesafen, glyphosate, glufosinate, MCPA, mesotrione, paraquat and sulcotrione.

12. The pesticide composition as claimed in claim 9, which comprises one or more water-insoluble active ingredients.

13. The pesticide composition as claimed in claim 9, wherein the total amount of the pesticides of component g) in the composition is greater than 100 g/L based on the acid equivalent thereof.

14. The pesticide composition as claimed in claim 9, wherein the total amount of the alkylglucamides of the formula (I) in the composition is from 20 to 250 g/L.

15. The pesticide composition as claimed in claim 9, wherein the content of the one or more ammonium salts b) is 10 to 500 g/L, based on the overall composition.

16. The pesticide composition as claimed in claim 9, wherein the composition comprises, one or more further adjuvants.

17. The pesticide composition as claimed in claim 9, which takes the form of a concentrate formulation which is diluted prior to use and contains 5% to 80% by weight, of the at least one water-soluble pesticide of component g) and 1% to 25% by weight, of the at least one alkylglucamide of component a).

18. The pesticide composition as claimed in claim 9, which takes the form of a spray liquor and comprises 0.001% to 10% by weight, of the at least one water-soluble pesticide of component g) and 0.01% to 1 A by weight, of the at least one alkylglucamide of component a).

19. A method for control and/or for abatement of unwanted plant growth, fungal disorders or insect infestation in plants comprising the step of contacting the unwanted plant growth, fungal disorders or insect infestation in plants with a pesticide composition comprising a) at least one alkylglucamide of the formula (I) ##STR00009## in which R1 is a linear or branched alkyl group having 5 to 9 carbon atoms, R2 is an alkyl group having 1 to 3 carbon atoms, b) at least one ammonium salt, c) propylene glycol, dipropylene glycol, mixtures of propylene glycol and dipropylene glycol, each optionally in a mixture with polypropylene glycol and/or polyethylene glycol, each having up to ten repeat units, d) water, e) optionally at least one cosolvent, f) optionally at least one auxiliary, p) at least one water-soluble pesticide, h) optionally at least one water-insoluble pesticide.

20. A method of protecting plants from harmful organisms, wherein the plant, the harmful organisms or their habitat is brought into contact with a pesticide composition comprising an inventive adjuvant composition comprising a) at least one alkylglucamide of the formula (I) ##STR00010## in which R1 is a linear or branched alkyl group having 5 to 9 carbon atoms, R2 is an alkyl group having 1 to 3 carbon atoms, b) at least one water-soluble ammonium salt, c) propylene glycol, dipropylene glycol, mixtures of propylene glycol and dipropylene glycol, each optionally in a mixture with polypropylene glycol and/or polyethylene glycol, each having up to ten repeat units, and d) water.

Description

WORKING EXAMPLES

Production

[0104] The use concentrations in the test are always based on the tested product and, with regard to the linear C8/10 glucamide itself, what is always meant is a stable solution with 50% active substance content in water/propylene glycol.

[0105] The solution with 50% active C8/10 glucamide substance was produced as follows: First of all, according to EP 0 550 637, C8/10 fatty acid methyl ester (methyl octanoate:methyl decanoate=55:45) is reacted with N-methylglucamine in the presence of 1,2-propylene glycol as solvent and obtained as a solid consisting of 90% active substance and 10% 1,2-propylene glycol. This solid was dissolved at 40 to 50 C. in water, so as to give a solution with a 50% content of linear C8/10 glucamide. This is a clear colorless solution.

[0106] Increasing the absorption of systemic active ingredients or herbicides and test systems for measurement of the promotion of penetration of active ingredients

[0107] Surfactants can also promote the absorption of (active) ingredients through membranes such as skin, films or the plant cuticle. As a finite-dose application, it is known for the single administration or application of a solution, cream, gel etc. to a membrane that the absorption of active ingredient can be influenced by some additives such as surfactants even after wetting. This effect is independent of the interfacial effect in water, is often highly concentration-dependent and takes place for the most part after evaporation of water and any solvents present as a result of the interaction, for example, with active ingredient, membrane and environmental factors. For various surfactants, it is observed after addition to active ingredient preparations that the penetration of a particular active ingredient is promoted to an enormous degree by some surfactants, whereas others are entirely ineffective (Cronfeld, P, Lader, K. Baur, P. (2001). Classification of Adjuvants and Adjuvant Blends by Effects on Cuticular Penetration, Pesticide Formulations and Application Systems: Twentieth Volume, ASTM STP 1400, A. K. Viets, R. S. Tann, J. C. Mueninghoff, eds., American Society for Testing and Materials, West Conshohocken, Pa. 2001).

[0108] The potential of the C8/10 glucamide, which is independent of the surfactant action, to promote foliar absorption of active agrochemical ingredients was determined in membrane penetration tests with apple or pear leaf cuticles. The plant cuticle is a lipophilic solubility membrane (lipid membrane) without pores or holes, and the results described are also expected for other nonporous lipophilic solubility membranes with these or other electrolyte active ingredients. The principle of the method has been published (e.g. WO-A-2005/194844; Baur, 1997; Baur, Grayson and Schnherr 1999; Baur, Bodelon and Lowe, 2012), and only the specifics and differences in the method are elucidated hereinafter. The leaf cuticles were enzymatically isolated in the manner described in the literature from apple leaves of orchard trees in a commercial fruit growing facility near Frankfurt am Main in 2011. The stomata-free cuticles were first dried under air and then installed into stainless steel diffusion cells. After application to the original upper side of the leaf and evaporation of the test liquid, i.e. of the aqueous preparations of the active ingredients without or with the C8/10-glucamide-containing spray liquids or comparative compositions, the diffusion cells were transferred into thermostatted blocks and charged with aqueous liquid. The water used to make up the aqueous test liquids was local tap water (of known composition). At regular intervals, samples were taken and, irrespective of the test system, the proportion of active ingredient penetrated was determined either by HPLC or scintillation measurement. In the system containing radiolabeled active ingredients (dicamba, 2,4-D, MCPA), the aqueous liquid was a phospholipid suspension and the total amount was exchanged. In all other HPLC variants, only an aliquot was taken. During the experiment, the temperature in the system (block, diffusion cells, liquids, etc.) and the air humidity above the spray coating on the cuticle were known exactly and were monitored. In the experiments, the relative air humidity was kept constant throughout at 56% relative air humidity (air over supersaturated calcium nitrate) or 60% relative air humidity (dew point method); the temperature was either constant throughout at 25 C. or RT 22(1) C. or the temperature was raised by 10 C. after 24 h hours. The analytical determination was effected either by means of HPLC (1290 Infinity, Agilent) or analysis of radioactivity (Tricarb, Perkin Elmer). HPLC separation was with a Kinetex column 302.1 mm, 2.6 C18 100A (Phenomenex), taking 20 L aliquots as the injection volume at the specified times. In the tests with radiolabeled substances, the sample volume was 0.5 mL and the measurement was effected via scintillation (Baur, Grayson and Schnherr 1999). In each case, the geometric mean values of the penetration for intact membranes at the mean measurement times are given. According to the variant (active ingredienttest additive/formulation), 7-8 repetitions were set up. The coefficient of variation was usually below 35%, but in individual cases may be up to 50%, which is a typical biological variability for penetration for numerous plants (Baur, 1997).

[0109] By way of example, the following adjuvant formulations (F) were tested with a widely differing ratio of C8/10 glucamide and ammonium sulfate. The spray liquid was local tap water with 85 ppm of Ca and 16 ppm of Mg, levels which are of relevance and potentially antagonistic for herbicide electrolytes. This tap water was in some cases enriched with calcium, such that a concentration of 177 ppm of Ca was attained, which corresponds to very hard water. The penetration test is of very good suitability for measuring the antagonism of Ca for the penetration of acids (see Uhlig, Baur and Schnherr 1998). This effect was measured with the formulations comprising ammonium sulfate. The same effects are expected with ammonium citrate and oxalate, and other anions that form sparingly soluble calcium salts. Much less significant but likewise relevant are antagonism by iron or magnesium, which can likewise be neutralized with the formulations F1-7. In the case of softer water (75 ppm of Ca), an enhancement of effect can also be achieved with other ammonium salts such as nitrate, chloride etc., or else with ammonium nitrate-urea combinations.

Formulations

[0110] F1 45% by weight of linear C8/10 glucamide, 5% by weight of propylene glycol and 20% by weight of ammonium sulfate, remainder water [0111] F2 10% by weight of linear C8/10 glucamide, 25% by weight of ammonium sulfate, 10% by weight of fructose-glucose syrup (55% by weight of fructose, 42% by weight of glucose), 3% by weight of propylene glycol, 0.03% by weight of defoamer (Momentive SAG 1572 SGS), remainder water [0112] F3 10% by weight of linear C8/10 glucamide, 25% by weight of ammonium sulfate, 10% by weight of polyglycerol (with 7-10 glycerol monomers), 3% by weight of propylene glycol, 0.03% by weight of defoamer (Momentive SAG 1572 SGS), remainder water [0113] F4 5% by weight of linear C8/10 glucamide, 35% by weight of ammonium sulfate, 10% by weight of fructose-glucose syrup (55% by weight of fructose, 42% by weight of glucose), 2.5% by weight of propylene glycol, 0.03% by weight of defoamer (Momentive SAG 1572 SGS), remainder water [0114] F5 15% by weight of linear C8/10 glucamide, 20% by weight of ammonium sulfate, 2% by weight of propylene glycol, 0.03% by weight of defoamer (Momentive SAG 1572 SGS), remainder water [0115] F6 is a 2.5:1 mixture of F1 and Synergen GL8 (an alkyl(hydroxyethyl)dimethylammonium chloride, Clariant) [0116] F7 is a 3:2 mixture of F1 and Synergen GL8 (an alkyl(hydroxyethyl)dimethylammonium chloride, Clariant) [0117] F8 is a mixture of the linear C8/10 glucamide in 25% by weight of AHL (ammonium nitrate-urea solution, Piasan 28) with 3 g/L linear C8/10 glucamide

[0118] The formulations F1-8 correspond to water-containing water-miscible SL formulations which are stable in any relationship. The glucamide itself and the concentrations set do not necessitate any biocide; the formulations go completely back into solution when thawed after storage at 20 C. and precipitation of ammonium sulfate. Standard storage tests (about 8 weeks at 40 C. or 2 weeks at 54 C.) do not alter the properties. The formulations can be diluted without any problem with all water qualities (CIPAC A,C,D, tap water, demineralized water).

Effect Examples for Active Ingredients

Test Substances for Penetration:

[0119] MCPA, iodosulfuron, 2,4-D (DMA), sulcotrione, mesotrione, clethodim,
dicamba (acid and DGA), saflufenacil, tembotrione

[0120] Effect examples for the increase in penetration with linear C8/10 glucamide compared to the active ingredient or an active ingredient-containing formulation alone and/or other comparators. The standard spray liquid was tap water with 85 ppm of Ca and 16 ppm of Mg. In each case, the agent alone and with addition of the test substance is shown.

[0121] The examples which follow with important active herbicidal ingredients each show the excellent suitability of the formulations comprising linear C8/10 glucamide with ammonium sulfate for promoting the penetration of a wide variety of different electrolyte active ingredients (herbicides here). The can lead to significantly better weed control, quicker rain resistance and better exploitation of the potential of active ingredients and, in individual cases, also to saving of active ingredient.

TABLE-US-00001 TABLE 1 Penetration of MCPA (potassium salt), (active ingredient concentration 1 g/L in spray liquid) Test product (conc.) Mean penetration* in % after time (n = 4-8) Spray liquor concentration 1.0 g/L ai 4 h 1 day MCPA potassium alone 1.6 7.2 F1 0.5% (inventive) 11.3 31.6 F2 0.5% (inventive) 9.2 31.1 F3 0.5% (inventive) 9.6 32.3 *25 C./56% rel. air humidity

[0122] The inventive formulations F1-3 lead to a 4- to 7-fold increase in the penetration of MCPA-potassium after 4 hours or one day.

TABLE-US-00002 TABLE 2 Penetration of 2,4-D DMA** with antagonistic calcium at 177 ppm Ca, simulating very hard water (active ingredient concentration 5 g/L of 2,4-D DMA in spray liquid) Test product (conc.) Mean penetration* in % after time (n = 4-8) Spray liquor concentration 5 g/L ai 4 h 1 day 2,4-D DMA alone 0.2 0.3 F2 0.5% (inventive) 15.4 14.4 F4 0.5% (inventive) 21.4 48.4 F5 0.5% (inventive) 4.8 15.0 F6 0.35% (inventive) 22.0 50.0 *25 C./56% rel. air humidity **DMA, dimethylamine

[0123] The inventive formulations F2-6 lead to a more than 10-fold increase in the penetration of 2,4-D DMA after 4 hours or one day. F6 shows a better effect at a lower use concentration. This shows a synergistic effect, since Synergen GL8 (30% in F6) itself does not show any effect on the penetration.

TABLE-US-00003 TABLE 3 Penetration of dicamba (acid) with tap water containing 85 ppm Ca (active ingredient concentration 1.0 g/L of 2,4-D DMA in spray liquid) Test product (conc.) Mean penetration* in % after time (n = 4-8) Spray liquor concentration 1.0 g/L ai 5 h 1 day Dicamba (acid) alone, in 4.4 12.4 normal tap water (85 ppm) F1 0.2% (inventive) 20.0 42.5 Genamin 267 7.0 26.2 (commercial tallowamine ethoxylate with 15 EO) *20 C./60% rel. air humidity

[0124] The inventive formulation F1 leads to a 3-4.5-fold increase in the penetration of dicamba acid after 5 hours or one day. This is quicker and more than with a tallowamine ethoxylate which is customary in the art. Since dicamba has significant volatility, the improved absorption can also suppress a reduction in the volatility and the deposition in non-targeted areas.

TABLE-US-00004 TABLE 4 Penetration of dicamba DGA** with antagonistic calcium at 177 ppm Ca, simulating very hard water (active ingredient concentration 2.5 g/L of dicamba DGA in spray liquid) Test product (conc.) Mean penetration* in % after time (n = 4-8) Spray liquor concentration 2.5 g/L ai 3 h 1 day Dicamba DGA SL500** 0.9 14.3 alone, in normal tap water (85 ppm) Dicamba DGA SL500** 0.2 3.8 alone, in tap water (177 ppm) F1 0.5% (inventive) 9.7 28.9 F2 0.5% (inventive) 8.4 34.3 F2 0.75% (inventive) 8.9 39.8 F3 0.5% (inventive) 6.7 34.4 F4 0.5% (inventive) 3.3 39.7 Premium Oil Concentrate 0.3 4.6 0.5% (commercial) *20 C./60% rel. air humidity **DGA, diglycolamine, from a soluble liquid formulation of the commercial products Clarity (BASF) or Sterling Blue (Winfield)

[0125] All formulations containing the linear C8/10 glucamide significantly increased the penetration. The higher the concentration of linear C8/10 glucamide, the more quickly the promotion of penetration occurred (F1>F2F3>F4). The crop oil concentrate had no effect at all in the case of the hard water, in spite of the additive content being twice as high.

TABLE-US-00005 TABLE 5 Penetration of sulcotrione (active ingredient concentration 0.2 g/L in spray liquid) Test product (conc.) Mean penetration* in % after time (n = 4-8) Spray liquor concentration 0.2 g/L ai 5 h 1 day Sulcotrione alone <1 <1 F1 0.25% (inventive) 1.8 8.7 F1 0.5% (inventive) 3.5 19.5 *20 C./60% rel. air humidity

[0126] The inventive formulation F1 leads to a concentration-dependent increase of more than 8-fold in the penetration of sulcotrione after 5 hours or one day.

TABLE-US-00006 TABLE 6 Penetration of mesotrione (active ingredient concentration 0.3 g/L in spray liquid) Test product (conc.) Mean penetration* in % after time (n = 4-8) Spray liquor concentration 0.3 g/L ai 1 day* 2 days* SC480 (Clariant) <1 <1 F1 0.25% (inventive) 12.9 22.9 F1 0.5% (inventive) 11.4 19.8 *25 C./60% rel. air humidity, **increase after 1 day to 35 C./60% rel. air humidity

[0127] The inventive formulation F1 leads to a concentration-dependent increase of more than 10-fold in the penetration of mesotrione after 1 day or 2 days.

TABLE-US-00007 TABLE 7 Penetration of mesotrione (active ingredient concentration 0.3 g/L in spray liquid) Test product (conc.) Mean penetration in % after time (n = 4-8) Spray liquor concentration 0.3 g/L ai 1 day* 2 days** SC480 (Clariant) 1.9 3.0 F1 0.3% (inventive) 3.8 12.8 F2 0.5% (inventive) 2.6 7.9 F2 1.0% (inventive) 16.4 33.9 F3 0.75% (inventive) 11.1 23.3 F4 0.5% (inventive) 17.0 17.1 F7 0.5% (inventive) 21.5 33.6 *25 C./60% rel. air humidity, **increase after 1 day to 35 C./60% rel. air humidity

[0128] All inventive formulations tested were effective with a very significantly concentration-dependent rise in the penetration of mesotrione in the case of F2 and a very good result for F1 even at 0.3%.

TABLE-US-00008 TABLE 8 Penetration of clethodim (active ingredient concentration 0.75 g/L in spray liquid) Test product (conc.) Mean penetration* in % after time (n = 4-8) Spray liquor concentration 0.75 g/L ai 12 h 1 day Status EC240 3.5 4.8 (commercial) F1 0.5% (inventive) 14.1 15.8 *25 C./56% rel. air humidity

[0129] The inventive formulation F1 leads to a 3- to 4-fold increase in the penetration of clethodim after 12 hours or 1 day.

TABLE-US-00009 TABLE 9 Penetration of saflufenacil** (active ingredient concentration 0.5 g/L in spray liquid) Test product (conc.) Mean penetration* in % after time (n = 4-8) Spray liquor concentration 0.5 g/L ai 12 h 1 day 2 days Sharpen SC285 + 0.4 0.5 0.8 0.5% AMS (commercial) F1 0.5% (inventive) 11.1 16.6 25.6 *25 C./56% rel. air humidity **pear leaf cuticles

[0130] The inventive formulation F1 leads to a more than 10-fold increase in the penetration of saflufenacil after 12 hours or 1-2 days.

TABLE-US-00010 TABLE 10 Penetration of iodosulfuron (active ingredient concentration 0.1 g/L in spray liquid) Test product (conc.) Mean penetration in % after time (n = 4-8) Spray liquor concentration 0.1 g/L ai 1 day* 2 days h** Husar WG20 (commercial) 7.1 8.3 Biopower 0.5% (commercial) 7.8 17.0 F1 0.5% (inventive) 42.5 62.5 Biopower 0.25% PLUS 23.4 41.2 F1 0.15% *20 C./56% rel. air humidity, **increase after 1 day to 30 C./56% rel. air humidity

[0131] The inventive formulation F1 leads to a more than 6-fold increase in the penetration of iodosulfuron after 1 day or 2 days. This is more than the Biopower standard at the same use concentration of 0.5%, and a combination of the two is likewise better at a concentration of 0.4%.

TABLE-US-00011 TABLE 11 Penetration of tembotrione (active ingredient concentration 0.4 g/L in spray liquid) with antagonistic calcium at 177 ppm Ca, simulating very hard water Test product (conc.) Mean penetration***** in % after time (n = 4-8) Spray liquor concentration 0.4 g/L ai 12 h* 1 day** Soberan SC420 <1 <1 (commercial) *** Aureo *** 0.25% + 3.3 4.2 0.1% AMS (commercial) Raizer 0.5% 1.3 1.5 (commercial) F4 0.5% (inventive) 10.1 17.6 (commercial) *20 C./56% rel. air humidity, **30 C./56% rel. air humidity *** Soberan: Mixture of tembotrione and isoxadifene (Bayer CropScience) **** Aureo (80% methylated seed oil + 20% emulsifier) **** pear leaf cuticles

[0132] F4 has a water content of nearly 50% and has thus shown, at a use concentration 30% lower than the combination of Aureo and AMS, much better promotion of penetration even with this very hard water.

[0133] Raizer (Farmoz, St Leonards, Australia) is a commercial adjuvant (comprising lecithin, propionic acid and nonionic surfactants) which is used as a water conditioner, in order to suppress the antagonistic effects of hard water. F4 is also distinctly superior to this market standard.

Dynamic Surface Tension (Interfacial Activity)

[0134] In the case of plants that are difficult to wet, such as the cereal plants wheat, barley, triticale, rye and oats, in the case of further large-area crops corn, rice, soya and oilseed rape, and also in the case of almost all weed grasses and numerous dicotyledonous weeds that are difficult to control, such as Chenopodium album or Euphorbium heterophyllum, the promotion of the adsorption of the spray liquid on the green parts of the plant is of crucial significance. This wetting agent effect was therefore also determined for the linear C8-C10 glucamide.

[0135] For a given application technique or parameters (nozzle, pressure, water application rate, distance from the plant surface), the value for the dynamic surface tension in [mN/m] correlates well with the adhesion on plants that are difficult to wet such as barley (cereal). A value of 50 mN/m (at 20-21 C.) with respect to water (72.8 mN/m) results in an improvement in the adhesion from zero adhesion to about 50% (Baur P, Pontzen R 2007. Basic features of plant surface wettability and deposit formation and the impact of adjuvants. In: R E Gaskin ed. Proceeding of the 8th International Symposium on Adjuvants for Agrochemicals. Publisher: International Society for Agrochemical Adjuvants (ISAA), Columbus, Ohio, USA). A value below 60 mN/m at 200 ms gives visibly better adsorption of aqueous spray liquids; in the case of standard flat jet nozzles, optimal wetting is achieved.

[0136] Table 12 shows that this value or a lower value is attained even at the low test concentration in water of 1.5 g/L (or 0.8 g/L for the active substance). Thus, the etherified lactate esters are outstandingly suitable for promoting the adsorption of agrochemicals on cereals (with corn, rice, millet/sorghum), banana, cabbage/oilseed rape, soya and other crop plants and harmful plants that are difficult to wet. The positive wetting and sticking effects do of course also apply to other organisms and synthetic surfaces or technical applications, for instance for attainment of thin coatings on or the cleaning of surfaces.

[0137] The dynamic surface tension values are shown hereinafter for the linear C8-10 glucamide alone and for some formulations.

TABLE-US-00012 TABLE 12 Dynamic surface tension of linear C8/10 glucamide (54%) Dynamic surface tension (in mN/m) Conc. (g/L) 20 ms 50 ms 100 ms 200 ms 0.3 (0.16) 72.8 72.3 71 70.4 1.5 (0.8) 63.5 59.0 57.3 55.0 3.0 (1.6) 55.0 50.3 47.5 45.4 Comparison Concentration Dyn. surface tension (commercial) (g/L) at 200 ms (mN/m) Tallowamine ethoxylates 1 54.1 3 49.5 Isotridecyl alcohol 1 46.1 ethoxylate **

TABLE-US-00013 TABLE 13 Degree of coverage after spray application Measurements of the degree of coverage on monocotyledonous plants such as wheat or, here, Pogonanthera spec. confirm optimal wetting for a concentration of 0.2% of the linear C8-10 glucamide. This applies to the pure product and to the formulations F1-F4. By way of example, the degree of coverage for F1 is shown below with application by means of a flat jet nozzle in a spray cabin. The application parameters were XR11002 nozzle (Teejet), spray pressure 3 bar, 150 L/ha of water; distance from nozzle to horizontally positioned leaf 45 cm: Formulation Concentration Degree of coverage [%] Water 7.5 F1 .sup.1 g/L 28.0 F1 2.5 g/L 57.5 F1 5.0 g/L 78.5

[0138] The degree of coverage is the area covered by the spray droplets after application on the leaf. A value of 100% corresponds to a continuous film, which is not the aim. The degree of coverage with water was below 5%, and was increased with F1 to 12% at 1 g/L, 30% at 2.5 g/L and 43% at 5 g/L.

Field Trials

[0139] By way of example, the effect of the linear C8/10 glucamide of formulation F1 was examined in field trials at the North Dakota State University by comparison with standards that are in practical use locally and the local standard practical conditions. In the tests, an amount of 360 grams of glyphosate acid as Touchdown Hitech or per 50 g of mesotrione as Callisto SC480 per hectare was deployed. The water application rate was 80 liters per ha. A flat jet nozzle was used at 3 bar. The control of the two important local weeds Setaria italica (SETIT) and Amaranthus spp. (AMASS) was scored after 14 days (Jul. 24, 2013) and 28 days (Aug. 8, 2013). The local positive standard is a combination of 10 g/L of the additive R-11 (nonylphenyl ethoxylate, Willbur-Ellis) combined with ammonium sulfate at likewise slightly more than 10 g/L. This was compared with the inventive formulation F1, which was tested at 1.5 g/L and 4.5 g/L.

TABLE-US-00014 TABLE 14 Control of the weeds Setaria italica and Amaranthus spp. with Touchdown Hitech with additives in practical use or inventive F1 Additive Conc. 14 days 28 days Standard g/L AMASS SETIT AMASS SETIT R- 11 10 88 99 88 95 R- 11 + AMS 10 + 10 91.7 99 90 93 F1 1.5 87 99 87 98 F1 4.5 90 99 92 96

[0140] The inventive formulation F1 leads to equally good or better control of the weeds with Touchdown Hitech than the market/practical standards. At the same time, the composition is much more economically viable, since the use concentration was more than 10 times lower.

TABLE-US-00015 TABLE 15 Control of the weeds Setaria italica and Amaranthus spp. with Callisto SC480 with additives in practical use or inventive F1 Additive Conc. 14 days 28 days Standard g/L AMASS SETIT AMASS SETIT R- 11 + AMS 10 + 10 33 15 33 13 F1 1.5 62 18 57 15 F1 4.5 53 13 63 13

[0141] The inventive formulation F1 leads to better control of the weeds with Callisto SC480 than the market/practical standards. At the same time, the composition is much more economically viable, since the use concentration is 4 to 10 times lower.