ACTIVE INGREDIENT COMPOSITIONS COMPRISING N-ALKENOYL-N-ALKYLGLUCAMIDES AND THE USE THEREOF

Abstract

The invention relates to active ingredient compositions comprising a) one or more active substances, and b) one or more N-alkenoyl-N-alkylglucamides of the formula I

##STR00001##

in which R1 is a linear or branched alkenyl group which has 7 to 16 carbon atoms and has a non-terminal double bond or a plurality of conjugated or non-conjugated double bonds, and R2 is an alkyl group having 1 to 4 carbon atoms.

The compounds of formula I can be used for reducing drift and for improving wettability when appyling active ingredient compositions.

Claims

1. An active ingredient composition comprising a) one or more active substances selected from the group consisting of pesticides, and b) one or more N-alkenoyl-N-alkylglucamides of the formula I ##STR00005## in which R1 is a linear or branched alkenyl group which has 11 to 15 carbon atoms and has a non-terminal double bond or a plurality of conjugated or non-conjugated double bonds, and R2 is an alkyl group having 1 to 4 carbon atoms.

2. (canceled)

3. The active ingredient composition as claimed in claim 1, wherein R1 has 12 to 14 carbon atoms.

4. The active ingredient composition as claimed in claim 3, wherein R1 is a dodecadienyl radical or a tetradecadienyl radical

5. The active ingredient composition as claimed in claim 1, wherein R1 is an undecenyl radical having a non-terminal double bond.

6. The active ingredient composition as claimed in claim 1, wherein R1 derives from a mixture of N-alkenyl acid methyl esters that comprises diunsaturated C.sub.13-alkenyl acid methyl esters, monounsaturated C14-alkenyl acid methyl esters, monounsaturated C.sub.15-alkenyl acid methyl esters and diunsaturated C.sub.15-alkenyl acid methyl esters.

7. The active ingredient composition as claimed in claim 1, wherein R2 is methyl.

8. (canceled)

9. The active ingredient composition as claimed in claim 1, wherein at least one of the pesticides is a contact pesticide and/or a soil-active pesticide.

10. The active ingredient composition as claimed in claim 1, wherein it takes the form of a spray liquid and comprises 0.00001% to 5% by weight of active substance(s) and 0.001% to 3% by weight of the N-alkenoyl-N-alkylglucamide(s) of the formula I, where the stated amounts are based on the overall spray liquid.

11. An N-alkenoyl-N-alkylglucamide of the formula I ##STR00006## in which R1 is an undec-8-enyl radical, a dodecadienyl radical, a tetradecadienyl radical, or wherein R1 derives from a mixture of N-alkenyl acid methyl esters that comprises diunsaturated C13-alkenyl acid methyl esters, monounsaturated C14-alkenyl acid methyl esters, monounsaturated C15-alkenyl acid methyl esters and diunsaturated C15-alkenyl acid methyl esters, and R2 is an alkyl group having 1 to 4 carbon atoms.

12. The N-alkenoyl-N-alkylglucamide as claimed in claim 11, wherein R2 is methyl.

13. An adjuvant composition comprising (A1) an N-alkenoyl-N-alkylglucamide of the formula I as claimed in claim 11, and (A2) a cosolvent.

13-20. (canceled)

21. A method of reducing drift and of simultaneously improving wettability when appyling an active ingredient composition, comprising a) one or more active substances selected from the group consisting of pesticides, and b) one or more N-alkenoyl-N-alkylglucamides of the formula I ##STR00007## in which R1 is a linear or branched alkenyl group which has 11 to 15 carbon atoms and has a non-terminal double bond or a plurality of conjugated or non-conjugated double bonds, and R2 is an alkyl group having 1 to 4 carbon atoms, wherein an aqueous spray liquid comprising the active ingredient composition is sprayed onto the species to be treated and/or the locus thereof, wherein the spray liquid comprises one or more N-alkenoyl-N-alkylglucamides of the formula I in amounts of 0.001% to 5% by weight, based on the total weight of the spray liquid.

22. The method as claimed in claim 21, in which at least one of the active substances is a pesticide, for control and/or for combating of weeds, fungal diseases or insect infestation.

23. The method as claimed in claim 21, wherein the active ingredient compositions comprise at least one contact pesticide and/or soil-active pesticide.

24. The method as claimed in claim 21, wherein the N-alkenoyl-N-alkylglucamide of the formula I is used for reducing drift and for improving wettability when appyling the active ingredient compositions, and does not lead to enhanced uptake of an active agrochemical ingredient into the target organism.

Description

EXAMPLE 1

Preparation of the N-alkenoyl-N-alkylglucamides of the Invention

[0179] Dodec-9-enoyl-N-methylglucamide was prepared from a commercially available dodec-9-enoylcarboxylic acid methyl ester by reaction with N-methylglucamine in propylene glycol as described in WO 92/06073. This gave a mixture which, as well as 90% by weight of the dodec-9-enoyl-N-methylglucamide of the formula (I) with R1=undec-8-enoyl radical and R2=CH.sub.3, also contained 10% by weight of propylene glycol from the reaction mixture.

[0180] The C13-15-alkenoyl-N-methylglucamide was prepared from a commercially available unsaturated C13-15-carboxylic acid methyl ester, mainly consisting of a complex mixture of mono- and polyunsaturated C13- and C15-alkenoyl methyl esters, by reaction with N-methylglucamine in propylene glycol as described in WO 92/06073. This gave a mixture which, as well as 90% by weight of the unsaturated C13-15-alkenoyl-N-methylglucamide of the formula (I) with R1=mono- and polyunsaturated C12-14-alkenyl radical and R2=CH.sub.3, also contained 10% by weight of propylene glycol from the reaction mixture.

[0181] Analogously, for comparison, the following non-inventive N-alkanoyl-N-methylglucamides were prepared from the corresponding linear saturated alkylcarboxylic acid methyl esters: C.sub.8-C.sub.14-alkanoyl-N-methylglucamide, dodecanoyl-N-methylglucamide, C.sub.12-C.sub.14-alkanoyl-N-methylglucamide.

EXAMPLE 2

Production of Sprya Liquids with N-alkenoyl-N-alkylglucamides

[0182] The composition of spray liquids A1-A18 is specified hereinafter. These spray liquids are produced by mixing the various test substances in water, and the appearance and stability of the spray liquid were assessed after 24 h.

TABLE-US-00002 TABLE 1 Amount Spray liquid Alkylglucamide [% by wt.] Appearance Stability A1 Dodec-9-enoyl-N- 0.05 cloudy stable methylglucamide homogeneous emulsion A2 Dodec-9-enoyl-N- 0.1 cloudy stable methylglucamide homogeneous emulsion A3 Dodec-9-enoyl-N- 0.2 cloudy stable methylglucamide homogeneous emulsion A4 C13-15-alkenoyl- 0.05 cloudy stable N- homogeneous methylglucamide emulsion A5 C13-15-alkenoyl- 0.1 cloudy stable N- homogeneous methylglucamide emulsion A6 C13-15-alkenoyl- 0.2 cloudy stable N- homogeneous methylglucamide emulsion A7 (non- dodecanoyl-N- 0.05 flocculation phase inventive) methylglucamide separation A8 (non- dodecanoyl-N- 0.1 flocculation phase inventive) methylglucamide separation A9 (non- dodecanoyl-N- 0.2 flocculation phase inventive) methylglucamide separation A10 (non- C12/14-alkanoyl- 0.05 flocculation phase inventive) N- separation methylglucamide A11 (non- C12/14-alkanoyl-N- 0.1 flocculation phase inventive) methylglucamide separation A12 (non- C8/14-alkanoyl-N- 0.05 flocculation phase inventive) methylglucamide separation A13 (non- C8/14-alkanoyl-N- 0.1 flocculation phase inventive) methylglucamide separation A14 (non- Genamin T 150 0.05 clear solution stable inventive) A15 (non- Genamin T 150 0.1 clear solution stable inventive) A16 (non- Genamin T 150 0.2 clear solution stable inventive) A17 (non- Synergen GA 0.1 clear solution stable inventive) A18 (non- 9-decenoyl-N- 0.1 clear solution stable inventive) glucamide

[0183] The inventive alkenoylglucamides (A1 to A6) are self-emulsifying in the spray liquid and form cloudy homogeneous emulsions that are stable over 24 h. By contrast, spray liquids comprising non-inventive saturated alkylglucamides (A7-A13) of similar chain length are not phase-stable and flocculate. Shorter-chain alkylglucamides, for example Synergen GA (C8/10 alkylglucamide) or 9-decenoyl-N-glucamide, are completely water-soluble and form a clear transparent spray liquid.

EXAMPLE 3

Dynamic Surface Tension

[0184] Dynamic surface tension was determined via the bubble pressure method (BP2100 tensiometer, Krss). Given a timespan of relevance for the spray application of agrochemicals in aqueous dilution (called the surface age in the bubble pressure method) of 200 milliseconds (ms), the value for dynamic surface tension in [mN/m] correlates 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 (0%) to about 50% (Baur P., Pontzen R.; 2007; Basic features of plant surface wettability and deposit formation and the impact of adjuvant; in R. E. Gaskin ed. Proceedings of the 8th International Symposium on Adjuvants for Agrochemicals; Publisher: International Society for Agrochemical Adjuvants (ISAA), Columbus, Ohio, USA).

[0185] It is additionally known from the literature that surface-active substances, for example tallowamine ethoxylates, that lower dynamic surface tension normally exhibit an adverse effect on spray drift and lead to sprays with an elevated proportion of fine droplets (Hilz et al., Spray drift review: The extent to which a formulation can contribute to spray drift reduction, Crop Protection 44 (2013) 75-83).

[0186] Surprisingly, the N-alkenoyl-N-alkylglucamides of the invention, in spite of low dynamic surface tension, show excellent drift-reducing properties (see tables 4 and 5).

TABLE-US-00003 TABLE 2 Dynamic surface tension [mN/m] Amount % by 20 50 100 200 Test substance wt. ms ms ms ms Dodec-9-enoyl-N-methylglucamide 0.03 70.0 66.1 61.9 58.6 Dodec-9-enoyl-N-methylglucamide 0.1 56.1 47.7 44.0 40.1 Dodec-9-enoyl-N-methylglucamide 0.3 44.5 38.5 36.0 33.4 C13-15-alkenoyl-N-methyl- 0.03 72.9 71.8 70.8 69.6 glucamide C13-15-alkenoyl-N-methyl- 0.1 70.6 67.4 62.3 58.0 glucamide C13-15-alkenoyl-N-methyl- 0.3 60.4 54.2 48.2 45.5 glucamide dodecanoyl-N-methylglucamide 0.03 70.6 67.3 63.0 57.9 dodecanoyl-N-methylglucamide 0.1 70.0 66.8 60.1 51.4 dodecanoyl-N-methylglucamide 0.3 67.0 61.9 58.8 48.7 Genamin T 150 0.03 68.2 65.5 62.2 59.0 Genamin T 150 0.1 64.3 60.3 57.5 54.5 Genamin T 150 0.3 60.0 56.6 53.4 50.7 Synergen OS 0.3 71.5 69.0 67.4 65.8 Synergen GA 0.03 71.4 70.8 70.4 70.7 Synergen GA 0.1 69.0 65.5 63.1 61.5 Synergen GA 0.3 55.1 50.3 47.1 45.5 dec-9-enoyl-N-methylglucamide 0.06 70.2 68.9 67.6 67.4 dec-9-enoyl-N-methylglucamide 0.125 66.4 63.7 61.8 61.0 dec-9-enoyl-N-methylglucamide 0.25 59.7 56.6 55.5 54.1

[0187] The results show that both of the tested N-alkenoyl-N-alkylglucamides of the formula I lowered the dynamic surface tension to a distinctly greater degree and are therefore distinctly better wetting agents compared to the saturated C12 variant of dodecanoyl-N-methylglucamide (C12, saturated) with similar chain length. Especially for Dodec-9-enoyl-N-methylglucamide (C12, unsaturated), the lowering of the dynamic surface tension is particularly large. Compared to commercially used wetting agents as well, such as Genamin T 150 (tallowamine ethoxylate), Dodec-9-enoyl-N-methylglucamide shows considerably better wetting properties. The anti-drift adjuvant Synergen OS does not show any significant lowering of the dynamic surface tension. Moreover, the lowering of the dynamic surface tension, given comparable concentrations for Dodec-9-enoyl-N-methylglucamide, is surprisingly much greater than in the case of other glucamides, for example Synergen GA or 9-decenoyl-N-methylglucamide.

EXAMPLE 4

Production of Spray Liquids with Tankmix Partner Formulation and N-alkenoyl-N-alkylglucamides

[0188] The composition of spray liquids B1-B14 is specified hereinafter. These spray liquids are produced by mixing a tankmix partner, for example ammonium sulfate (AMS) or pesticide formulations, the test substance and water. Homogeneous spray solutions are obtained.

TABLE-US-00004 TABLE 3 Amount of Amount tankmix of test Spray Tankmix partner substance liquid partner [% by wt.] Test substance [% by wt.] B1 (non- AMS 0.5 inventive) B2 AMS 0.5 Dodec-9-enoyl-N- 0.1 methylglucamide B3 AMS 0.5 C13-15-alkenoyl-N- 0.1 methylglucamide B4 (non- Flint WG 50 0.015 inventive) B5 Flint WG 50 0.015 Dodec-9-enoyl-N- 0.1 methylglucamide B6 Flint WG 50 0.015 C13-15-alkenoyl-N- 0.1 methylglucamide B7 (non- Liberator 0.30 inventive) B8 Liberator 0.30 Dodec-9-enoyl-N- 0.1 methylglucamide B9 Liberator 0.30 C13-15-alkenoyl-N- 0.1 methylglucamide B10 (non- Ascra Xpro 1.25 inventive) B11 Ascra Xpro 1.25 Dodec-9-enoyl-N- 0.1 methylglucamide B12 Ascra Xpro 1.25 C13-15-alkenoyl-N- 0.1 methylglucamide B13 (non- Affirm095 0.055 inventive) SG B14 Affirm095 0.055 Dodec-9-enoyl-N- 0.1 SG methylglucamide

EXAMPLE 5

Measurement of Droplet Size Distribution

[0189] A Malvern Spraytec real-time spray sizing system was used to determine the droplet size distribution. For this purpose, the system (STP5311, Malvern Instruments GmbH, Heidelberg, Germany) was installed in a specially constructed spray cabin, with the option of being able to model real spray applications as carried out in practice with freely adjustable pressure for various hydraulic nozzles and freely adjustable distances (nozzle-target surface). The spray cabin can be darkened and all disruptive parameters can be eliminated. For the measurements, the ID(3)12002 (Lechler) injector nozzles were used. The pressure set was varied, and mean pressure was kept constant at 3 bar for the measurements reported hereinafter. The temperature and relative air humidity varied between 21.5 C. and 29 C. and between 33% and 56% respectively. In each test series, tap water was measured as internal standard.

[0190] The Spraytec measurement was made at the setting of 1 kHz, since measurements at 2.5 kHz or higher, and also other influencing parameters such as additional suction, were found to be negligible. The measurement in the spray was kept constant at a position with distances of exactly 29.3 cm from the nozzle and 0.4 cm from the perpendicular below the nozzle. The measurements were made within 5 seconds, and the mean of 6 repetitions is reported as the proportion by volume of the droplets having diameters <90 m (Vol 90), <105 m (Vol 105) and <150 m (Vol 150) (percentage standard error 0.5%-2.5%).

[0191] As a further measurement parameter, the proportion by volume of the droplets having diameter <210 m (Vol 210) was determined and expressed in relation to the proportion by volume of droplets having diameter <105 m (Vol 210 / Vol 105). In addition, the percentage reduction in the proportion by volume of droplets having diameter <105 m in the case of use of spray liquids containing the test substances was calculated in comparison to the use of tap water as internal standard (Red 105).

TABLE-US-00005 TABLE 4 Droplet size distribution for ID(3)12002 injector nozzle (at 3 bar) using spray liquids A1-A17 (for composition see table 1). Vol 90 Vol 105 Vol 150 Vol 210/ Red 105 Spray liquid Test substance [% by vol.] [% by vol.] [% by vol.] Vol 105 [%] water 1.88 3.00 6.79 4.02 0.00 A1 dodec-9-enoyl-N- 0.93 1.41 2.95 4.27 52.88 methylglucamide A2 dodec-9-enoyl-N- 0.89 1.33 2.94 5.14 55.79 methylglucamide A3 dodec-9-enoyl-N- 1.06 1.63 3.80 5.16 45.64 methylglucamide A4 C13-15-alkenoyl-N- 0.88 1.34 2.56 3.36 55.30 methylglucamide A5 C13-15-alkenoyl-N- 0.93 1.41 2.70 3.41 52.88 methylglucamide A6 C13-15-alkenoyl-N- 0.95 1.47 3.06 4.07 50.89 methylglucamide A7 (non- dodecanoyl-N- 1.00 1.45 2.69 3.14 51.47 inventive) methylglucamide A8 (non- dodecanoyl-N- 0.87 1.33 2.44 2.97 55.64 inventive) methylglucamide A9 (non- dodecanoyl-N- 1.45 2.27 4.72 3.63 24.38 inventive) methylglucamide A14 (non- Genamin T 150 3.18 4.69 9.88 3.79 46.53 inventive) A15 (non- Genamin T 150 3.26 5.29 12.87 4.49 65.26 inventive) A16 (non- Genamin T 150 3.85 6.49 16.53 4.68 102.64 inventive) A17 (non- Synergen OS 0.88 1.30 2.36 3.16 56.70 inventive)

[0192] Typically, wetting agents, for example Genamin T 150 (tallowamine ethoxylate, V14-V16), which reduce dynamic surface tension lead to a drastic increase in fine droplet content. The results show that both the N-alkenoyl-N-alkylglucamides tested, in addition to their excellent wetting properties, surprisingly bring about a reduction in the fine droplet content, comparable to the commercially available anti-drift adjuvant Synergen OS. Especially surprising is the effect for dodec-9-enoyl-N-methylglucamide (C12, unsaturated), which, in spite of the particularly significant lowering of the dynamic surface tension, brings about a distinct reduction in the fine droplet content.

TABLE-US-00006 TABLE 5 Droplet size distribution for ID(3)12002 injector nozzle (at 3 bar) using spray liquids B1-B14 (for composition see table 3). Test substance/ Vol 90 Vol 105 Vol 150 Vol 210/ Red 105 Spray liquid tankmix partner [% by vol.] [% by vol.] [% by vol.] Vol 105 [%] water 1.96 3.13 7.05 3.97 0.00 B1 (non- /AMS 1.78 2.85 6.55 4.14 6.25 inventive) B2 dodec-9-enoyl-N- 0.99 1.54 3.49 4.89 49.51 methylglucamide/ AMS B3 C13-15-alkenoyl-N- 0.91 1.39 2.76 3.66 54.43 methylglucamide/ AMS B4 (non- /Flint WG 50 0.81 1.28 2.74 3.77 58.94 inventive) B5 dodec-9-enoyl-N- 0.79 1.17 2.46 4.66 62.53 methylglucamide/Flint WG 50 B6 C13-15-alkenoyl-N- 0.81 1.22 2.34 3.59 60.91 methylglucamide/Flint WG 50 B7 (non- /Liberator 1.44 2.23 4.82 3.94 28.55 inventive) B8 dodec-9-enoyl-N- 0.73 1.11 2.27 4.20 64.35 methylglucamide/ Liberator B9 C13-15-alkenoyl-N- 0.77 1.20 2.51 4.06 61.67 methylglucamide/ Liberator B10 (non- /Ascra Xpro 2.53 4.40 11.63 5.05 38.10 inventive) B11 dodec-9-enoyl-N- 1.07 1.61 3.58 4.77 49.44 methylglucamide/ Ascra Xpro B12 C13-15-alkenoyl-N- 1.02 1.58 3.74 5.21 50.58 methylglucamide/ Ascra Xpro B13 (non- /Affirm095 SG 1.21 1.89 4.09 3.87 41.08 inventive) B14 dodec-9-enoyl-N- 1.18 1.85 4.40 5.12 42.27 methylglucamide/ Affirm095 SG

[0193] The results show that both N-alkenoyl-N-alkylglucamides, even in the presence of typical tankmix partners such as AMS or commercially available pesticide formulations, bring about a reduction in the fine droplet content.

EXAMPLE 6

Penetration Characteristics of Soil-Active or Contact Active Ingredients using the Example of Metribuzin and Test System for Measurement of the Enhancement of Penetration of Active Ingredients

[0194] Surfactants can affect 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).

[0195] The potential of the test substances, which is independent of the surfactant action, to promote foliar absorption of active agrochemical ingredients was determined in membrane penetration tests with apple leaf cuticles using the example of metribuzin. In the case of soil-active pesticides, for example metribuzin, and in the case of particular contact pesticides, greatly increased uptake of the active ingredient is harmful for efficacy. Efforts are therefore being made to find additives that promote wetting but only slightly increase the uptake of the active ingredient, such that only a minimum portion of the active ingredient is taken up into the leaf.

[0196] It is known that short-chain alkylglucamides, for example Synergen GA (N-methyl-N-octanoyl/decanoylglucamine), lead only to a slight increase in penetration, if any, via elevated diffusion through the cuticle of green plant parts or generally at the the plant level. Especially in the case of active ingredients having a molecular weight greater than 300 g/mol and the melting point of greater than 100 C., additives that greatly enhance uptake into the target organism are necessary for the biological efficacy thereof. But even in the case of active ingredients having smaller molecular weight, for example metribuzin (see table 6), the uptake of soil herbicides is increased by such additives (see table 6). This is usually at the cost of prolonged action owing to a shift in the active ingredient dose from the soil to plant parts above the ground, and hence poorer soil action. Examples of such penetration enhancers are additives comprising methylated vegetable oil (e.g. rapeseed oil methyl ester or soybean oil methyl ester) or particular alkoxylated alcohols. It has been found that the inventive N-alkenoyl-N-alkylglucamides of the formula I promote wetting and adhesion, but only very slightly increase the uptake of the active ingredient into the leaf, if at all.

[0197] 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 stone fruit growing facility near Frankfurt am Main in 2016. 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 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, aliquot samples were taken and the proportion of active ingredient penetrated was determined by HPLC. During the experiment, the temperature in the system (block, diffusion cells, liquids, etc.) and the air humidity above the spray deposit on the cuticle were known exactly and were monitored. In the experiment, relative air humidity was constant throughout at 56% relative air humidity (air over supersaturated calcium nitrate) at a constant 10 C. The analytical determination by means of HPLC (1290 Infinity, Agilent) was effected thereafter with a Kinetex column 302, 1 mm, 2.6 C18 100 A (Phenomenex), taking a 20 L aliquot as injection volume at the specified times. 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 below 35%, which is a typical biological variability for penetration for numerous plants (Baur, 1997).

TABLE-US-00007 TABLE 6 Penetration of metribuzin (formulation of Sencor 600 SC with active ingredient concentration 2.25 g/L in spray liquid) in the presence of various test substances Mean penetration for metribuzin (amount of active ingredient 2.25 g/L) after time (n = 4-8) in % Amount % by Test substance wt. 1 day 2 days 1.4 3.9 Synergen GA 0.25 5.1 4.9 Synergen OS 0.14 10.1 16.4 dodec-9-enoyl-N-methylglucamide 0.05 2.9 4.6 dodec-9-enoyl-N-methylglucamide 0.1 3.9 6.5 dodec-9-enoyl-N-methylglucamide 0.14 5.7 8.6 C13-15-alkenoyl-N-methylglucamide 0.05 3.6 4.3 C13-15-alkenoyl-N-methylglucamide 0.1 6.9 9.8 C13-15-alkenoyl-N-methylglucamide 0.14 6.7 11.7 Strikelock 0.05 17.1 24.7 Strikelock 0.1 23.6 42.7 Strikelock 0.14 31.8 55.6 Hasten 0.05 11.4 25.6 Hasten 0.1 39.1 58.4 Hasten 0.14 45.0 72.3 *10 C./56% rel. air humidity

[0198] The table shows that both N-alkenoyl-N-alkylglucamides, similarly to the short-chain alkylglucamide Synergen GA (N-methyl-N-octanoyl/decanoylglucamine), by comparison with methylated vegetable oil-based products (Synergen OS, Strikelock and Hasten), lead only to minor promotion of penetration. Given comparable concentrations, the uptake of the N-alkenoyl-N-alkylglucamides is lower by more than two times compared to Synergen OS, more than five times compared to Strikelock, and more than seven times compared to Hasten.

EXAMPLE 7

[0199] The plant compatibility of dodec-9-enoyl-N-methylglucamide and C13-15-alkenoyl-N-methylglucamide at the abovementioned concentrations of 0.1, 0.3, 0.8, 1.0, 1.5, 2 and 3 g/L is just as good as that of Synergen GA and N-methyl-N-nonanoylglucamine. After application to indicator plants (described, for example, in DE102014018274A1), there were no necroses or other symptoms such as leaf curl-up or deformation in any case, whereas an ethoxylated lauryl alcohol at 1 g/L that was also tested caused distinct necroses within one day.