Use of alkyl ether sulfates for improving efficacy of herbicides

Abstract

The present invention relates to the use of alkyl ether sulfates of formula (I) for increasing the herbicidal effect of one or more herbicidal compounds: [R-O-(A-O) n-SO3]-M + (I), wherein M + is a cation; a is a C2-C3 alkanediyl group; r is a branched C10-alkyl group; and n is an integer in the range of 1 to 10. The invention also relates to a method for controlling undesired plants, wherein at least one alkyl ether sulfate of formula (I) and at least one herbicide compound are applied to these undesired plants or their habitats. Furthermore, the invention relates to a herbicidal formulation comprising at least one alkyl ether sulfate of formula (I) and at least one herbicide compound, and to an aqueous spray comprising at least one alkyl ether sulfate of formula (I) and at least one herbicide compound.

Description

[0001] The present invention relates to the use of alkyl ether sulfates of formula (I) as defined below for improving the herbicidal effect of one or more herbicidal compounds, and to a method for controlling undesirable vegetation, wherein at least one alkyl ether sulfate of formula (I) and at least one herbicide compound as defined below are applied to the undesirable vegetation or its habitat.

[0002] The present invention also relates to a herbicidal formulation comprising at least one alkyl ether sulfate of formula (I) and at least one herbicide compound as defined below. In addition, the present invention relates to an aqueous spray liquid comprising at least one alkyl ether sulfate of formula (I) and at least one herbicide compound as defined below. Background Art

[0003] In agriculture, herbicides are widely used to control the growth of undesirable plants such as weeds, because undesirable plants compete with crop plants for water, nutrients and sunlight, and thus reduce crop yield and crop quality. Herbicides can be applied to clear farmland of undesirable plants before sowing or planting crop plants. However, depending on the crop and its compatibility with the herbicide, herbicides can also be applied to the field where the crop plants are growing.

[0004] For effectiveness, herbicides must overcome multiple barriers (morphological, biological, and environmental) to their entry into target plants. For example, trichomes on leaf surfaces can reduce herbicide efficacy by intercepting spray droplets before they contact the epidermal surface. Environmental stress (e.g., hot, dry weather) may produce a thicker wax layer than normal, or increase other defensive structures, such as reducing the metabolic and transport processes of the plant, which are required for adequate weed control. Therefore, the biological activity of the herbicide may be unsatisfactory or at least less than expected. Although higher application rates can achieve better herbicidal efficacy, this is usually impossible due to regulatory reasons, and this is undesirable due to ecological and economic reasons. On the contrary, there is great interest in improving the bioavailability (also referred to as efficacy or bioefficacy) of herbicides in order to reduce the application rate in this way.

[0005] It is well known that the efficacy of herbicides can be improved by certain adjuvants. Adjuvants (from the Latin adiuvare: to assist) are commonly used in agriculture to improve the performance of herbicides or other pesticides, including better mixing and handling, improved effectiveness and safety, better distribution, and reduced drift. Broadly speaking, adjuvants are ingredients that assist or modify the action of the main active ingredient. Adjuvants can be roughly divided into three groups: activators, spray modifiers, and effect modifiers.

[0006] Activators will mainly improve the efficacy of herbicides through various modes of action.Activators are typically surfactants, particularly nonionic surfactants (NIS), including silicone surfactants, oils, such as high surfactant oils, crop oil concentrates, vegetable oil concentrates and modified vegetable oil concentrates, and wetting agents.Spray modifiers will change the characteristics of aqueous sprays, and therefore promote to target herbicide sprays, reduce the drift of herbicides in the air or can make spraying more easily adhere to plants by various mechanisms.Effect modifiers help minimize processing and application problems.They have widened the conditions under which herbicides can be used or maintained the integrity of spray solutions.For example, effect modifiers reduce foaming, improve solubility, change pH or reduce spray drift.Compared with activators, spray modifiers and effect modifiers do not usually improve the biological efficacy of pesticides, but promote the use of aqueous pesticide sprays.

[0007] A review of adjuvant technology is given by Z. Pacanosky, Herbicide Adjuvants (2015), DOI: 10.5772 / 60842. A summary of commercially available adjuvants for herbicides (hereinafter, herbicide adjuvants) is given by BG Young et al. (eds.) "Compendium of Herbicide Adjuvants", 13th edition (2016), Purdue Extension and Southern Illinois University (https: / / mdc.itap.purdue.edu / item.asp?Item_Number=PPP-115).

[0008] Water-soluble herbicides such as glufosinate are chemicals that penetrate and damage and / or destroy parasites in or on plant cells, tissues or plants. The preparations containing water-soluble herbicides are usually used in the form of liquid or solid concentrated preparations, and these preparations are convenient for the user to handle or provide the effectiveness of the raising of active ingredient. These preparations are typically diluted with water before use and then applied by spraying. Water-soluble concentrates (soluble liquids, SL) are the particularly important forms of herbicide preparations, and wherein active ingredient is often used as the water-soluble salt obtained by neutralizing the herbicide in acid form with suitable alkali.

[0009] Particularly in the case of water-soluble herbicidal compounds such as glufosinate-ammonium, the type and amount of adjuvant used have a decisive influence on the efficacy of the formulation. Aqueous formulations of glufosinate-ammonium are known, for example, from EP-A-0048436, EP-A-0336151, EP-A-1093722, WO 2007 / 147500A1 or WO 2007 / 092351A2, in which alkyl ether sulfates are used as adjuvants.

[0010] So far, C 12 -C 16 Alkyl ether sulfates of an alkyl chain and 1 to 10 alkyleneoxy units, such as sodium lauryl ether sulfate (SLES) or sodium myristyl ether sulfate, have been used as adjuvants in commercially available formulations of glufosinate-ammonium. However, they are associated with certain disadvantages.

[0011] One of their main disadvantages is their efficacy as adjuvants. Although alkyl ether sulfates enhance the effectiveness of the active ingredient in the formulation, the enhancement effect of the active ingredient is not satisfactory. In addition, the biological activity of the active ingredient depends on the ratio of the active ingredient to such alkyl ether sulfates. Therefore, in order to achieve a satisfactory adjuvant effect with conventional alkyl ether sulfates, a large amount of such alkyl ether sulfates must be applied in the formulation. However, if the amount of such conventional alkyl ether sulfates is too high, the viscosity of the formulation may become too high to be easy to handle or spray. Therefore, there is a continuous need to find adjuvants for formulations containing water-soluble herbicides, which can satisfactorily enhance the herbicidal efficacy of the active ingredient in the formulation and at the same time have no adverse effect on the physicochemical properties of the formulation. Summary of the invention

[0012] Therefore, the object of the present invention is to provide further compounds which enhance the activity of herbicides, in particular water-soluble herbicides. In addition, such compounds should not have an adverse effect on the physicochemical properties of the formulations, and in the best case they should lead to better foaming behavior in order to facilitate the handling or spraying of formulations containing water-soluble herbicides such as glufosinate-ammonium.

[0013] Surprisingly, it has now been found that alkyl ether sulfates of formula (I) as described herein enhance the effectiveness of herbicide compounds to a greater extent than the above alkyl ether sulfates such as sodium lauryl ether sulfate or sodium myristyl ether sulfate which are frequently used as adjuvants for herbicides such as glufosinate-ammonium.

[0014] The present invention therefore relates to the use of at least one alkyl ether sulfate of formula (I) for increasing the herbicidal effect of one or more herbicide compounds,

[0015] [RO-(AO) n -SO3]- M + (I)

[0016] in

[0017] M + It is a cation;

[0018] A is a C2-C3 alkanediyl group, such as CH2CH2, CH2CH(CH3) or a combination thereof;

[0019] R is branched C 10 -alkyl, in particular 2-propylheptyl or isodecyl; and

[0020] n is an integer in the range of 1-10, preferably in the range of 1-8, particularly in the range of 1-7, especially in the range of 1-5.

[0021] The invention also relates to a method for controlling undesirable vegetation, wherein at least one alkyl ether sulfate of formula (I) as defined herein and at least one herbicide compound are applied to these undesirable vegetation or their habitat.

[0022] The alkyl ether sulfates of formula (I) can be easily incorporated into conventional herbicide formulations of one or more herbicide compounds, in particular into liquid herbicide formulations. Therefore, a further aspect of the present invention is a herbicidal formulation comprising:

[0023] i. at least one alkyl ether sulfate having formula (I) as defined herein; and

[0024] ii. at least one herbicide compound.

[0025] To control undesirable vegetation, the at least one alkyl ether sulfate of formula (I) as defined herein and the at least one herbicide compound are usually applied as an aqueous spray liquid.

[0026] i. at least one alkyl ether sulfate having formula (I) as defined herein; and

[0027] ii. at least one herbicide compound.

[0028] The alkyl ether sulfates with formula (I) of the present invention have several advantages. First, they improve the weeding effect of herbicidal compounds. In particular, they improve the effectiveness of different herbicidal compounds (e.g., glufosinate and salts of glufosinate), and the degree of improvement is greater than other alkyl ether sulfates such as SLES known as activator adjuvants of herbicides. In particular, they improve the efficacy of herbicides for undesirable plants that are difficult to control and therefore expand the applicability of one or more corresponding herbicidal compounds. For this reason, the alkyl ether sulfates with formula (I) can be co-formulated with herbicidal compounds in aqueous herbicide formulations and in non-aqueous herbicide formulations. It can also be mixed (bucket mixed) with conventional formulations of herbicidal compounds in aqueous spraying liquids. DETAILED DESCRIPTION

[0029] As used herein, "herbicide" refers to one or more agents, compounds, and / or compositions having weed suppressive and / or herbicidal activity.

[0030] As used herein, "herbicidal compound" refers to a single compound, especially an organic compound, having weed suppressive and / or herbicidal activity.

[0031] As used herein, the terms "herbicidal effect", "effectiveness of the herbicide" and "efficacy of the herbicide" are used synonymously. The terms "improving the herbicidal effect" and "enhancing the herbicidal effect" refer to increasing or enhancing the herbicidal activity of the corresponding herbicide compound against a certain undesirable plant. This means that the combined use of the herbicide compound and the alkyl ether sulfate having the formula (I) provides greater herbicidal activity against the target plant at the same application rate of the herbicide compound compared to the activity of the herbicide compound at a given application rate in the absence of the alkyl ether sulfate having the formula (I).

[0032] As used herein, the terms "control" and "combat" are synonymous and refer to the inhibition of growth, control of growth, reduction of growth, or outright destruction of undesirable plants.

[0033] As used herein, the terms "unwanted plants," "unwanted vegetation," "unwanted species," "noxious plants," "weeds," "unwanted weeds," "volunteer plants," or "noxious weeds" are used synonymously.

[0034] As used herein, the terms "action improver", "action improver system", "accelerator" and "adjuvant" are used synonymously.

[0035] Here and throughout the description, the terms "wt %", "wt.-%", "wt. %", "weight percent" and "% by weight" are used synonymously.

[0036] Here and throughout the specification, the term "plurality of herbicidal compounds" is to be understood as "more than one herbicidal compound" and thus includes "mixtures of herbicidal compounds". As used herein, the term "mixture of herbicidal compounds" refers to a physical and / or chemical mixture comprising at least one herbicidal compound.

[0037] As used herein, the term "herbicide compound(s)" refers to one or more herbicide compounds.

[0038] Within the context of the present invention, the general names of the radicals have the following meanings.

[0039] The term "alkyl" refers to a group generally having 1 to 20 carbon atoms (C1-C 20 alkyl), especially 1 to 10 carbon atoms (C1-C 10 alkyl), in particular a straight or branched saturated alkyl group having 1 to 6 carbon atoms (C1-C6 alkyl) or 1 to 6 carbon atoms (C1-C4 alkyl), including methyl, ethyl, n-propyl, 2-propyl, 2-methylpropyl (isopropyl), n-butyl, 2-butyl, isobutyl, tert-butyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2- dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, and 1-ethyl-2-methylpropyl.

[0040] The terms "alkylene" and "alkanediyl" refer to straight-chain or branched divalent alkyl groups typically having 2 to 4 carbon atoms (C2-C4 alkylene), such as 1,2-ethanediyl (=CH2CH2), 1,2-propylenediyl (=CH2CH(CH3)), 1,3-propylenediyl (=CH2CH2CH2), 1,2-butanediyl (=CH2CH(CH2CH3)), 1,3-butanediyl (=CH2CH2CH(CH3)), 1,4-butanediyl (=CH2CH2CH2CH2) and 1-methyl-1,2-propylenediyl (=CH(CH3)CH(CH3)).

[0041] According to the present invention, the alkyl ether sulfates of formula (I) are alkyl ether sulfates having a branched C 10-alkyl, especially 2-propylheptyl or isodecyl as the remaining part of the alkyl group; 10 - a linker between the alkyl and sulfate groups formed by 1 to 10 C2-C3-alkyleneoxy units AO - (AO) n -; and a cation as a counter ion of the sulfate group. Therefore, the alkyl ether sulfate having formula (I) is also referred to as a branched C 10 - Alkyl ether sulfates, in particular 2-propylheptyl ether sulfate or isodecyl ether sulfate.

[0042] The term "2-propylheptyl" refers to a branched C 10 -alkyl, wherein the heptyl remainder has a propyl remainder as the only substituent in position 2. The propyl substituent is a straight chain propyl (n-propyl), and likewise, the heptyl is straight chain except for the propyl in position 2.

[0043] The term "isodecyl" refers to a branched decyl group having at least one methyl group, in particular 1, 2, 3 or 4 methyl groups, which are bonded to a tertiary carbon atom, i.e. a CH group, of R of formula (I). Examples of isodecyl groups include, for example, 2-methyl-1-nonyl, 8-methyl-1-nonyl, 3,5-dimethyloctyl, 5,7-dimethyloctyl, 2,4,6-trimethylheptyl and mixtures thereof.

[0044] In a preferred embodiment of the present invention, R is 2-propylheptyl.

[0045] In another group of preferred embodiments of the present invention, R is an isodecyl group having at least one methyl group bonded to a tertiary carbon atom of R of formula (I).

[0046] Cation M + It may carry a single cationic charge, i.e. it is a monovalent cation or it may carry more than one cationic charge, for example 2 or 3 cationic charges, and is therefore multivalent. It is obvious to the skilled person that in the case of multivalent cations, for reasons of electroneutrality, the cation M in formula (I) + It refers to the cationic equivalent of a cation. Preferably, the cation M + It’s unit price.

[0047] In formula (I), the cation M + M may be any cation suitable for agricultural purposes. The cation may be monovalent, i.e. it carries a single cationic charge, or polyvalent, i.e. it carries more than one cationic charge. In this case, M + Suitable cations include alkali metal cations, such as sodium or potassium ions, alkaline earth metal cations, such as calcium ions, ammonium (NH4 +), and an organic amine-based cation. Preferably, M + The monovalent cation M of the alkyl ether sulfate of formula (I) is + Preferably selected from the group consisting of: alkali metal cations, such as sodium or potassium cations, ammonium (NH4 + ) and H 4-m NR 1 m + , where R 1 Selected from the group consisting of: alkyl, in particular C1-C4-alkyl, which is optionally substituted by hydroxy, methoxy, amino, alkylamino or dialkylamino, cycloalkyl, (Alk-NR')BN(R")2, (CH2CH2O) k CH2CH2OH and (CH2CH(CH3)O) n CH2CH(CH3)OH, wherein n is 0, 1 or 2, k is 0, 1 or 2, Alk is alkylene, in particular C2-C4-alkylene, B is alkylene, in particular C2-C4-alkylene, R' is hydrogen or alkyl, in particular hydrogen or C1-C4-alkyl, R" is hydrogen or alkyl, in particular hydrogen or C1-C4-alkyl, and m is an integer in the range of 1 to 4, in particular in the range of 1 to 3. In particular, R 1 is a C2-C4-alkyl group substituted by one hydroxyl group or one methoxy group. Particularly preferred substituted ammonium cations are 4-m NR 1 m + is an ammonium cation wherein m is 1, 2 or 3 and R 1 It is C1-C4-alkyl substituted by one hydroxyl group or one methoxy group, such as 2-hydroxyethyl or 2-hydroxypropyl.

[0048] Cation M + Suitable examples are, but are not limited to, alkali metal cations, such as sodium, potassium and lithium cations, and substituted or unsubstituted ammonium cations, such as NH4 + ammonium cation, hydroxyethylammonium cation, di(hydroxyethyl)ammonium cation, tri(hydroxyethyl)ammonium cation, 2-hydroxypropylammonium cation, di(2-hydroxypropyl)ammonium cation and tri(2-hydroxypropyl)ammonium cation.

[0049] Preferably, the cation M + is sodium or a substituted or unsubstituted ammonium cation, more preferably having the formula H as described herein 4-m NR 1 m + In particular, M + is sodium or a substituted or unsubstituted ammonium cation, more preferably having the formula H as described herein4-m NR 1 m + A substituted or unsubstituted ammonium cation wherein m is 1, 2 or 3 and R 1 It is a C1-C4-alkyl group substituted by one hydroxyl group or one methoxy group, such as hydroxyethyl or 2-hydroxypropyl.

[0050] According to the invention, the variable n in formula (I) is an integer in the range of 1 to 10, preferably in the range of 1 to 8, in particular in the range of 1 to 7, especially in the range of 1 to 5, for example n is 1, 2, 3, 4 or 5.

[0051] The alkyl ether sulfate of formula (I) is typically a mixture of compounds with different n. The average value of n is typically in the range of 1 to 10, preferably in the range of 1.1 to 7.0, in particular in the range of 1.5 to 6.0, more preferably in the range of 1.7 to 5.0. Any reference to the average value of n refers to the numerical average value of the repeating units AO per molecule, i.e. to the relative molar amount of the repeating units AO relative to R.

[0052] The variable A in formula (I) is a C2-C3 alkanediyl, in particular 1,2-ethanediyl (=CH2CH2), 1,2-propylenediyl (=CH2CH(CH3)) or a combination thereof. For n>1, the repeating units AO of the part may be identical or different. Preferably, A is CH2CH2 or a combination of CH2CH2 and CH2CH(CH3). In other words, the repeating units AO in the part are preferably ethyleneoxy (=CH2CH2O) or 1,2-propyleneoxy (=CH2CH(CH3)O) units. In the following, ethyleneoxy is also referred to as EO and propyleneoxy is referred to as PO.

[0053] In a particular group of embodiments (i), the moiety -(AO) in formula (I) n -It's EO n , wherein n is in the range of 1 to 10, preferably in the range of 1.1 to 5.0, particularly in the range of 1.5 to 4.5, more preferably in the range of 1.7 to 3.5 on average. The alkyl ether sulfate of formula (I) of embodiment (i) can be described by the following formula (Ii):

[0054] [RO-EO n -SO3] - M + (Ii)

[0055] Among them, R, EO, M + and n are as defined herein.

[0056] Particularly preferred examples of alkyl ether sulfates having the formula (Ii) are alkyl ether sulfates having the formula (Ii) wherein n is about 2 on average, ie in the range of 1.8 to 2.2.

[0057] In another specific group of embodiments (ii), the moiety -(AO) in formula (I) n -It's PO p EO q , wherein p is an integer in the range of 1 to 9, particularly 1 to 5 and especially 1 or 2, and q is an integer in the range of 1 to 9, particularly 1 to 5 and especially 1 to 4, p+q=n and wherein the average value of p+q is in the range of 1 to 10, preferably in the range of 1.1 to 7.0, particularly in the range of 1.5 to 6.0, more preferably in the range of 1.7 to 5.0. In part PO p EO q In the embodiment (ii), the EO and PO repeating units may be randomly or blockwise distributed. The alkyl ether sulfate having formula (I) of embodiment (ii) may be described by the following formula (I-ii):

[0058] [RO-PO p EO q -SO3] - M + (I-ii)

[0059] Among them, R, EO, PO, M + , p and q are as defined herein, and wherein the EO and PO repeating units may be randomly or blockwise distributed in part of the PO p EO q middle.

[0060] Particularly preferred examples of the alkyl ether sulfates having the formula (I-ii) are those having the formula (I-ii) wherein p is in the range of 0.7 to 1.9 on average, and q is in the range of 1.1 to 3.6.

[0061] In a particular group of embodiments (iii), the alkyl ether sulfate of formula (I) is a mixture of alkyl ether sulfates of groups (i) and (ii) of embodiments. In such a mixture, the average value of p is preferably in the range of 0.2 to 4.0, in particular in the range of 0.5 to 2.0, and the average value of q is preferably in the range of 0.5 to 4.8 and in particular in the range of 1.0 to 3.6, wherein the average value of p+q is preferably in the range of 1.1 to 5.0, in particular in the range of 1.5 to 4.5, more preferably in the range of 1.7 to 3.5.

[0062] Suitable examples of particularly preferred alkyl ether sulfates of formula (I), (Ii) and (I-ii) include, but are not limited to

[0063] - sodium 2-propylheptyl ether sulfate, ammonium 2-propylheptyl ether sulfate, hydroxyethylammonium 2-propylheptyl ether sulfate, di(hydroxyethyl)ammonium 2-propylheptyl ether sulfate, tri(hydroxyethyl)ammonium 2-propylheptyl ether sulfate, 2-hydroxypropylammonium 2-propylheptyl ether sulfate, di(2-hydroxypropyl)ammonium 2-propylheptyl ether sulfate, tri(2-hydroxypropyl)ammonium 2-propylheptyl ether sulfate,

[0064] -sodium isodecyl ether sulfate, potassium isodecyl ether sulfate, ammonium isodecyl ether sulfate, hydroxyethylammonium isodecyl ether sulfate, di(hydroxyethyl)ammonium isodecyl ether sulfate, tri(hydroxyethyl)ammonium isodecyl ether sulfate, 2-hydroxypropylammonium isodecyl ether sulfate, di(2-hydroxypropyl)ammonium isodecyl ether sulfate, tri(2-hydroxypropyl)ammonium isodecyl ether sulfate, i.e., alkyl ether sulfates of formula (I), wherein M is selected from sodium, potassium, ammonium, hydroxyethylammonium, di(hydroxyethyl)ammonium, tri(hydroxyethyl)ammonium, 2-hydroxypropylammonium, di(2-hydroxypropyl)ammonium or tri(2-hydroxypropyl)ammonium, wherein the ether portion in formula (I) is -(AO) n - is EO as described for groups (i) and (ii) of the embodiments n or PO p EO q In such particularly preferred alkyl ether sulfates of formula (I), the numerical average value of the variable n is preferably in the range from 1.1 to 7, in particular in the range from 1 to 4, in particular n is 1, 2 or 3, and wherein the average value of n is preferably in the range from 1.1 to 5.0, in particular in the range from 1.5 to 4.5, more preferably in the range from 1.7 to 3.5.

[0065] In particular, the alkyl ether sulfate of formula (I) is the ammonium salt of 2-propylheptyl ether sulfate, wherein M + Yes H 4- m NR 1 m + , where R 1 is as defined above and is in particular selected from the group consisting of unbranched or branched alkyl groups having preferably 1 to 4 carbon atoms, OH-substituted alkyl groups having preferably 2 to 4 carbon atoms, such as CH2CH2OH and CH2CH(OH)CH3, and m is an integer in the range of 1 to 4, in particular 1, 2 or 3, wherein the variable n is preferably in the range of 1 to 5, in particular in the range of 1 to 3, in particular n is 2, and wherein the average value of n is preferably in the range of 1.1 to 5.0, in particular in the range of 1.5 to 4.5 and in particular in the range of 1.7 to 3.5. Among these alkyl ether sulfates, particular preference is given to alkyl ether sulfates in which M + Yes H 4-m NR 1m + , where R 1 is as defined above and is in particular selected from the group consisting of OH-substituted alkyl having preferably 2 to 4 carbon atoms, such as CH2CH2OH and CH2CH(OH)CH3, and m is 1, 2 or 3.

[0066] The alkyl ether sulfates of the formula (I) according to the invention can be prepared by sulfating C2-C3-alkoxylated 2-propylheptan-1-ol of the formula (II) in the following manner:

[0067] RO-(AO) n -H(II)

[0068] It is sulfated in a manner known per se using sulfuric acid or a sulfuric acid derivative such as chlorosulfonic acid and subsequently neutralized to give an alkyl ether sulfate having formula (I). These processes can be carried out analogously to the alkyl ether sulfates described in WO 2005 / 077893 and the references cited therein. In formula (II), R, A and n are as defined for formula (I).

[0069] According to a preferred embodiment of the present invention, R in formula (I) is 2-propylheptyl or contains at least 90% by weight of 2-propylheptyl based on the total weight of the radicals R in formula (I). These compounds are prepared by sulfating C2-C3-alkoxylated 2-propylheptyl-1-ol of formula (II). C2-C3-alkoxylated 2-propylheptyl-1-ol of formula (II) is itself based on 2-propylheptyl alcohol.

[0070] 2-Propylheptanol is a Guerbet alcohol which can be obtained, for example, by dimerizing the corresponding primary alcohol at high temperature (eg 180° C. to 300° C.) in the presence of a basic condensing agent such as potassium hydroxide.

[0071] According to another preferred embodiment of the present invention, R in formula (I) is an isodecyl group as defined herein, or comprises at least 90% by weight of an isodecyl group as defined herein, based on the total weight of the groups R in formula (I). Isodecyl refers to a branched decyl group having at least one methyl group, in particular 1, 2, 3 or 4 methyl groups, which are bonded to the tertiary carbon atom of R, i.e. a CH group. In this group of embodiments, R is particularly derived from C 10 -oxo alcohol. In the following, C 10 -Oxo alcohol represents C 10 -alcohol mixture, the main component of which is characterized by having at least one methyl group bonded to a tertiary carbon atom of R, in particular in the 2-position relative to the OH group. 10-Oxoalcohols are typically obtained by hydroformylation of 1-nonene or 1-isononene. Isononene is typically obtained by oligomerization of propylene followed by fractionation of the oligomer mixture to obtain a fraction in which the portion of isononene is at least 90% by weight, based on the total weight of hydrocarbons in the fraction.

[0072] In a specific embodiment of the present invention, R in formula (I) comprises

[0073] - 0.1 to 99% by weight, in particular 1 to 70% by weight, especially 10 to 50% by weight, based on the total weight of the radicals R in formula (I), of 2-propylheptyl; and

[0074] - 1 to 99.9% by weight, in particular 30 to 99% by weight, especially 50 to 90% by weight, of isodecyl groups, based on the total weight of the radicals R in formula (I);

[0075] Therein, the total weight of 2-propylheptyl and isodecyl, based on the total weight of radicals R in formula (I), is at least 90% by weight, preferably at least 95% by weight, in particular at least 99% by weight.

[0076] Preferably, the amount of alkyl ether sulfate having formula (I) used is such that the weight ratio of alkyl ether sulfate having formula (I) to herbicide compound is in the range of 1:10 to 10:1, particularly in the range of 1:5 to 7:1, and particularly in the range of 1:1 to 6:1.

[0077] As described above, the alkyl ether sulfates of formula (I) improve the herbicidal effect of one or more herbicidal compounds compared to the use of one or more herbicidal compounds alone.

[0078] In particular, the alkyl ether sulfates having the formula (I) are able to enhance the herbicidal effect of the herbicide compounds of groups (a) to (o):

[0079] (a) herbicidal compounds from the group of glutamine synthetase inhibitors;

[0080] (b) herbicidal compounds from the group of enolpyruvylshikimate 3-phosphate synthase inhibitors (EPSP inhibitors);

[0081] (c) herbicidal compounds from the group of acetolactate synthase inhibitors (ALS inhibitors);

[0082] (d) herbicidal compounds from the group of protoporphyrinogen-IX oxidase inhibitors;

[0083] (e) herbicidal compounds from the group of auxin herbicides and auxin transport inhibitors;

[0084] (f) herbicide compounds from the group of photosynthesis inhibitors;

[0085] (g) herbicidal compounds from the group of lipid biosynthesis inhibitors (acetyl-CoA carboxylase inhibitors, ACCase inhibitors);

[0086] (h) lipid biosynthesis inhibitors other than ACCase inhibitors;

[0087] (i) bleaching agent herbicides;

[0088] (j) 7,8-dihydropteroate synthase inhibitors (DHP inhibitors);

[0089] (k) mitotic inhibitors;

[0090] (l) Very long chain fatty acid synthesis inhibitors (VLCFA inhibitors);

[0091] (m) cellulose biosynthesis inhibitors;

[0092] (n) decoupler herbicide;

[0093] (o) other herbicides selected from the group consisting of brombutal, cypermethrin, cypermethrin methyl, cypermethrin, cumyluron, cypermethrin and its salts and esters, dalapon, dazomethon, dimethoate, dimethoate-methyl sulfonate, thiamethoxam, DSMA, dymron, endothal and its salts, ethoxybencarb, cypermethrin-isopropyl, cypermethrin-methyl, cypermethrin-M-isopropyl, cypermethrin-M-methyl, Flurenol, flurenol-butyl, flurprimidol, flufenol, flufenol-ammonium, indole, maleic hydrazide, flusulfuron, metamidine, isoxathiapiprolin, methyl azide, methyl bromide, methyl-flufenuron, methyl iodide, MSMA, oleic acid, oxazithromycin, nonanoic acid, chlorpyrifos, quinaloxaline, tetflupyrolimet, cypermethrin, and 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (CAS 499223-49-3) and its salts and esters, and 6-chloro-4-(2,7-dimethyl-1-naphthyl)-5-hydroxy-2-methyl-pyridazin-3-one (CAS 2414510-21-5) (HST inhibitor; FMC).

[0094] Thus, the herbicide compound is selected from at least one herbicide compound of groups (a) to (o) as defined above.

[0095] Particularly preferably, the herbicide compound comprises a herbicide compound of group (a), in particular selected from the group consisting of glufosinate, glufosinate salts and combinations thereof.

[0096] Examples of herbicide compounds of group (a) include, but are not limited to, bilanaphos (bialaphos), bialaphos-sodium, glufosinate, glufosinate-S and glufosinate salts, such as glufosinate-ammonium.

[0097] Glufosinate (CAS Reg. No. 51276-47-2) - IUPAC name (2RS)-2-amino-4-[hydroxy(methyl)phosphinoyl]butyric acid, or 4-[hydroxy(methyl)phosphinoyl]-DL-homoalanine) or DL-4-[hydroxy(methyl)phosphinoyl]-DL-homoalanine salt - and its agronomically acceptable salts, in particular glufosinate-ammonium (IUPAC name: (2RS)-2-amino-4-(methylphosphinyl)butyrate ammonium, CAS Reg. No. 77182-82-2) are known. US 4,168,963 describes phosphorus-containing compounds having herbicidal activity, of which in particular phosphinothricin (2-amino-4-[hydroxy(methyl)phosphinoyl]butyric acid; common name: glufosinate) and its salts have acquired commercial importance in the field of agrochemistry (agricultural chemistry).

[0098] For example, glufosinate and its salts, such as glufosinate ammonium, and their herbicidal activity have been described, for example, by F. Schwerdtle et al., Z. Pflanzenkr. Pflanzenschutz [Journal of Plant Diseases and Plant Protection], 1981, Special Issue IX, pp. 431-440.

[0099] Formulations of glufosinate and its salts as the racemate are commercially available, for example, under the trade names Basta™ and Liberty™.

[0100] Glufosinate is represented by the following structure (IV):

[0101]

[0102] The compound of formula (IV) is a racemate.

[0103] Glufosinate is a racemate of two enantiomers, only one of which shows sufficient herbicidal activity (see, for example, US 4265654 and JP 92448 / 83). Although various methods for preparing L-Glufosinate (and corresponding salts) are known, mixtures known in the art do not point to stereochemistry, which means that there is a racemate (e.g., WO2003024221, WO 2011104213, WO 2016113334, WO 2009141367).

[0104] In one embodiment of the invention, the term "glufosinate" as used in the present invention typically comprises about 50% by weight of the L-enantiomer and about 50% by weight of the D-enantiomer; and in another embodiment of the present invention, greater than 70% by weight of the L-enantiomer; preferably greater than 80% by weight of the L-enantiomer; more preferably greater than 90% of the L-enantiomer, most preferably greater than 95% of the L-enantiomer. The L-enantiomer of glufosinate is also known as refined glufosinate.

[0105] Glufosinate and its salts in the form of its racemate and formulations thereof are commercially available, for example, under the trade names Basta™ and Liberty™.

[0106] In one embodiment, the herbicide compound is selected from the racemic glufosinate mixture as described above, wherein the glufosinate comprises about 50% by weight of the L-enantiomer and about 50% by weight of the D-enantiomer.

[0107] In another embodiment, the herbicide compound is glufosinate, wherein at least 70% by weight of the glufosinate is L-glufosinate or a salt thereof.

[0108] L-Glufosinate, which has the IUPAC name (2S)-2-amino-4-[hydroxy(methyl)phosphonyl]butanoic acid (CAS Reg. No. 35597-44-5) and is also known as glufosinate-ammonium, is commercially available or can be prepared, for example, as described in WO 2006 / 104120, US5530142, EP 0248357 A2, EP 0249188 A2, EP 0344683 A2, EP 0367145 A2, EP 0477902 A2, EP 0127429 and J. Chem. Soc. Perkin Trans. 1, 1992, 1525-1529.

[0109] Preferably, the salt of glufosinate or (L)-glufosinate is sodium, potassium or ammonium (NH4 +) salts, in particular, for L-glufosinate, ammonium glufosinate (IUPAC name: (2S)-2-amino-4-(methylphosphinate)butyrate ammonium, CAS Registry No. 73777-50-1), sodium glufosinate (IUPAC name: sodium (2S)-2-amino-4-(methylphosphinate)butyrate; CAS Registry No. 70033-13-5) and potassium glufosinate (IUPAC name: potassium (2S)-2-amino-4-(methylphosphinate)butyrate).

[0110] In a particular set of embodiments, the herbicide compound comprises a glufosinate salt selected from the group consisting of sodium, potassium or ammonium glufosinate (NH4 + )Salt.

[0111] Thus, the herbicide compound preferably comprises either (L)-phosphinothricin-ammonium or (L)-phosphinothricin-sodium or (L)-phosphinothricin-potassium and (L)-phosphinothricin as the free acid. Particularly preferred is (L)-phosphinothricin-ammonium, i.e., ammonium (NH4 + )Salt.

[0112] In a particular set of embodiments, the herbicide compound of group (a) is a L-glufosinate salt, which is particularly selected from the group consisting of sodium, potassium and ammonium (NH4) L-glufosinate. + Even more preferably, the herbicide compound of group (a) is an L-glufosinate salt selected from the group consisting of glufosinate-ammonium, glufosinate-sodium and glufosinate-potassium.

[0113] In particular, the herbicide compound is the ammonium salt of L-glufosinate.

[0114] The herbicide compound of group (a), in particular glufosinate as described above or its salts as described herein, may be the only herbicide compound used in combination with the compound of formula (I).

[0115] However, the compound of formula (I) can also be used in combination with at least two herbicidal compounds. In this case, the herbicidal compound used in combination with the compound of formula (I) comprises in particular a herbicidal compound of group (a), in particular glufosinate or its salt as described above, and at least one further herbicidal compound selected from groups (b) to (o):

[0116] (b) herbicidal compounds from the group of enolpyruvylshikimate 3-phosphate synthase inhibitors (EPSP inhibitors);

[0117] (c) herbicidal compounds from the group of acetolactate synthase inhibitors (ALS inhibitors);

[0118] (d) herbicidal compounds from the group of protoporphyrinogen-IX oxidase inhibitors;

[0119] (e) herbicidal compounds from the group of auxin herbicides and auxin transport inhibitors;

[0120] (f) herbicide compounds from the group of photosynthesis inhibitors;

[0121] (g) herbicidal compounds from the group of lipid biosynthesis inhibitors (acetyl-CoA carboxylase inhibitors, ACCase inhibitors);

[0122] (h) lipid biosynthesis inhibitors other than ACCase inhibitors;

[0123] (i) bleaching agent herbicides;

[0124] (j) 7,8-dihydropteroate synthase inhibitors (DHP inhibitors);

[0125] (k) mitotic inhibitors;

[0126] (l) Very long chain fatty acid synthesis inhibitors (VLCFA inhibitors);

[0127] (m) cellulose biosynthesis inhibitors;

[0128] (n) Decoupler herbicides;

[0129] (o) other herbicides selected from the group consisting of: brombutyric acid chloranil, chloranil methyl, cyproconazole, benzylpyrasulfuron, cyprosulfuron and its salts and esters, dalapon, dazomethanil, diazepam, diazepam-methyl sulfonate, thiamethoxam, DSMA, cyproconazole, cyprothiocarb and its salts, ethoprop, chloranil, chloranil-isopropyl ester, chloranil-methyl ester, chloranil-M-isopropyl ester, chloranil-M-methyl ester Ester, chlorpyrifos, chlorpyrifos-butyl, furafil, cypermethrin, chlorpyrifos ammonium, indole, maleic hydrazide, fluazifop, metamifop, isoxathiapiprolin, methyl azide, methyl bromide, methyl-chlorpyrifos, methyl iodide, MSMA, oleic acid, oxazithromycin, nonanoic acid, chlorpyrifos, chlorpyrifos-butyl, fluazifop, chlorpyrifos, and 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (CAS 499223-49-3) and its salts and esters, and 6-chloro-4-(2,7-dimethyl-1-naphthyl)-5-hydroxy-2-methyl-pyridazin-3-one (CAS 2414510-21-5) (HST inhibitor; FMC).

[0130] Suitable examples of herbicide compounds of group (b) of enolpyruvylshikimate 3-phosphate synthase inhibitors (EPSP inhibitors) include, but are not limited to, glyphosate, glyphosate-isopropylammonium salt, glyphosate-trimethylsulfonate, glyphosate-ammonium salt, glyphosate-diammonium salt, glyphosate-dimethylammonium salt, glyphosate-monoethanolamine salt, glyphosate-sodium salt, glyphosate-potassium salt, glyphosate-guanidine salt, agricultural salts and derivatives thereof.

[0131] Suitable salts of glyphosate are, for example, but not limited to, glyphosate-ammonium, glyphosate-diammonium, glyphosate-dimethylammonium, glyphosate-isopropylammonium, glyphosate-potassium, glyphosate-sodium, glyphosate-trimethylsulfide and ethanolamine and diethanolamine salts, preferably glyphosate-diammonium, glyphosate-isopropylammonium and glyphosate-trimethylsulfide (phosphosulfate).

[0132] Acetolactate synthase inhibitors (ALS inhibitors) (also called AHAS inhibitors or inhibitors of acetohydroxyacid synthase) of group (c) of herbicide compounds are compounds which have a mode of action which comprises the inhibition of a step in the biosynthesis of branched-chain amino acids in plants and which belong to group B of the HRAC classification system (see HRAC, Classification of Herbicides According to Mode of Action).

[0133] Suitable examples of herbicidal compounds of group (c) of ALS inhibitors include, but are not limited to:

[0134] imidazolinone herbicides, such as imazapic, imazamethabenz, imazamethabenz-methyl, imazamox, imazapyr, imazaquin, and imazethapyr and their salts;

[0135] Sulfonylurea herbicides, such as amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, chlorimuron, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, cyclosulfamuron, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron, flavonoids zasulfuron), flucetosulfuron, flupyrsulfuron, flucetosulfuron-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron, iodosulfuron-methyl-sodium, iofensulfuron, iodosulfuron-sodium, mesosulfuron, mesosulfuron-methyl, methylazole metazosulfuron, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, primisulfuron, primisulfuron-methyl, propyrisulfuron, prosulfuron, pyrazosulfuron, pyrazosulfuron-ethyl, rimsulfuron, methylpyrisulfuron Sulfometuron, sulfometuron-methyl, sulfosulfuron, thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenuron, bensulfuron-methyl, triflusulfuron, triflusulfuron-methyl, trifloxysulfuron, trifloxysulfuron-sodium, triflusulforon and tritosulfuron and their salts and esters;

[0136] triazolopyrimidine herbicides and sulfonanilides, such as cloransulam, cloransulam-methyl, diclosulam, florasulam, flumetsulam, metosulam, penoxsulam, pyrimisulfan and pyroxsulam, and their salts and esters;

[0137] Pyrimidinyl (thio)benzoate herbicides, such as bispyribac, pyribenzoxim, pyriftalid, pyrimisulfan, pyrithiobac, pyriminobac, their salts and esters, such as bispyribac-sodium, pyribenzoxim-sodium and pyriminobac-methyl, as well as 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid-1-methylethyl ester (CAS 420138-41-6), 4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]-benzoic acid propyl ester (CAS 420138-40-5) and N-(4-bromophenyl)-2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]benzylamine (CAS 420138-01-8); and

[0138] Sulfonylamino-carbonyl-triazolinone herbicides such as flucarbazone, propoxycarbazone, thiencarbazone and triafamone and their salts and esters such as flucarbazone-sodium, propoxycarbazone-sodium and thiencarbazone-methyl.

[0139] In particular, the herbicide of group (c) is selected from the group consisting of imidazolinone herbicides and salts thereof, in particular selected from the group consisting of imazapic, imazamox, imazapic, imazaquin, imazethapyr, combinations thereof, salts thereof and combinations of salts thereof.

[0140] Suitable salts of imidazolinone herbicides are imazamox-methyl salts, imazamox salts, metazamox salts, metazamox salts. Suitable salts of imazamox acid are, for example, imazamox acid-ammonium. Suitable salts of imazamox-methyl are, for example, imazamox-methyl ammonium and imazamox-isopropylammonium. Suitable salts of metazamox are, for example, metazamox-ammonium and metazamox-isopropylammonium. Suitable salts of metazamox are, for example, metazamox-ammonium and metazamox-isopropylammonium. Suitable salts of metazamox are, for example, metazamox-ammonium. Suitable salts of imazamox are, for example, imazamox-ammonium and imazamox-isopropylammonium.

[0141] Protoporphyrinogen-IX-oxidase inhibitors (PPO inhibitors) of group (d) of herbicide compounds are compounds which have a mode of action which comprises the inhibition of a step in the biosynthesis of chlorophyll in plants and which belong to group E of the HRAC classification system (see HRAC, Classification of Herbicides According to Mode of Action, http: / / www.plantprotection.org / hrac / MOA.html ).

[0142] Suitable examples of herbicidal compounds of group (d) of protoporphyrinogen-IX oxidase inhibitors (PPO inhibitors) include, but are not limited to:

[0143] · Pyrimidinedione herbicides, such as benzfendizone, butafenacil, saflufenacil, tiafenacil, ethyl [3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]acetate (CAS 353292-31-6), 1-methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione and 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)-1H-pyrimidine-2,4-dione (CAS 212754-02-4) and their salts, in particular the lithium, sodium, potassium, ammonium or substituted ammonium salts as defined above, in particular mono-, di- and tri-C1-C8-alkylammonium salts, such as methylammonium, dimethylammonium and isopropylammonium;

[0144] triazolinone herbicides, for example azafenidin, bencarbazone, carfentrazone, carfentrazone-ethyl, ipfencarbazone and sulfentrazone and their salts, in particular the sodium, potassium, ammonium or substituted ammonium salts as defined above, in particular mono-, di- and tri-C1-C8-alkylammonium salts, such as methylammonium, dimethylammonium and isopropylammonium, and their esters, in particular the C1-C8-alkyl esters, such as the methyl, ethyl or isopropyl esters;

[0145] Diphenyl ether herbicides, such as ethoxyfen, acifluorfen, acifluorfen-sodium, aclonifen, chlormethoxynil, bifenox, chlomethoxyfen, chlornitrofen, etnipromid, fluorodifen, fluoroglycofen, fluoroglycofen-ethyl, fluofloxacin, ronitrofen, fomesafen, fomesafen-sodium, fucaomi, furyloxyfen, halosafen, lactofen, nitrofen, nitrofluorfen and oxyfluorfen and their salts, in particular the sodium, potassium, ammonium or substituted ammonium salts as defined above, in particular mono-, di- and tri-C1-C8-alkylammonium salts, such as methylammonium, dimethylammonium and isopropylammonium, and their esters, in particular the C1-C8-alkyl esters, such as the methyl, ethyl or isopropyl esters;

[0146] N-phenyl(phthalimide) herbicides, for example fluthiacet, fluthiacet-methyl, cinidon, cinidon-ethyl, flumioxazin, pentoxazone, flumiclorac, flumiclorac-pentyl, flumipropyn and 2-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-4,5,6,7-tetrahydro-isoindole-1,3-dione (CAS 1300118-96-0). Also included are salts of indolone and flufenoxalic acid, in particular the sodium, potassium, ammonium or substituted ammonium salts thereof as defined above, in particular mono-, di- and tri-C1-C8-alkylammonium salts, such as isopropylammonium salts, and esters of indolone and flufenoxalic acid, in particular the C1-C8-alkyl esters thereof, such as the methyl, ethyl and isopropyl esters;

[0147] N-phenyl-oxadiazolone herbicides, such as oxadiazon and oxadiargyl;

[0148] Phenylpyrazole herbicides, such as pyraflufen, pyraflufen-ethyl, and fluazolate;

[0149] · pyridazinone herbicides, such as flufenpyr and flufenpyr-ethyl; and

[0150] Other herbicides, such as pyraclonil, chlorphthalim, cyclopyranil, profluazol, thidiazimin, trifludimoxazin, epyrifenacil, N-ethyl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452098-92-9), N-tetrahydrofurfuryl-3-(2,6-dichloro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 915396-43-9), N-ethyl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452099-05-7), N-tetrahydrofurfuryl-3-(2-chloro-6-fluoro-4-trifluoromethylphenoxy)-5-methyl-1H-pyrazole-1-carboxamide (CAS 452100-03-7), 3-[7-fluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-1,5-dimethyl-6-thioxo-[1,3,5]triazinane-2,4-dione (CAS 451484-50-7), 1-methyl-6-trifluoromethyl-3-(2,2,7-trifluoro-3-oxo-4-prop-2-ynyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-1H-pyrimidine-2,4-dione (CAS1304113-05-0), (E)-4-[2-chloro-5-[4-chloro-5-(difluoromethoxy)-1H-methyl-pyrazol-3-yl]-4-fluoro-phenoxy]-3-methoxy-but-2-enoic acid methyl ester (CAS 948893-00-3), and 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)-1H-pyrimidine-2,4-dione (CAS212754-02-4), 2-[2-chloro-5-[3-chloro-5-(trifluoromethyl)-2-pyridyl]-4-fluorophenoxy]-2-methoxy-acetic acid methyl ester (CAS1970221-16-9), 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridyl]oxy]phenoxy]-acetic acid methyl ester (CAS 2158274-96-3), 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]acetic acid methyl ester (CAS2158274-50-9), 2-[[3-[2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-1,2,4-triazol-1-yl]-4-fluoro-phenoxy]-2-pyridinyl]oxy]acetic acid methyl ester (CAS2271389-22-9), 2-[[3-[2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-1,2,4-triazol-1-yl]-4-fluoro-phenoxy]-2-pyridinyl]oxy]acetic acid methyl ester (CAS2271389-22-9), 2,4-triazol-1-yl]-4-fluoro-phenoxy]-2-pyridinyl]oxy]ethyl acetate (CAS2230679-62-4), 2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]-acetic acid methyl ester (CAS2158275-73-9), 2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]-acetic acid methyl ester (CAS2158275-73-9), -4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]ethyl acetate (CAS2158274-56-5), 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]-N-(methylsulfonyl)-acetamide (CAS2158274-53-2), 2-[[3-[[3-chloro-6-[3,6 -dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]-N-(methylsulfonyl)-acetamide (CAS2158276-22-1), 3-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl]-4,5-dihydro-5-methyl-5-isoxazolecarboxylic acid ethyl ester (CAS1949837-17-5).

[0151] Auxin herbicides and auxin transport inhibitors (also called synthetic auxins) of group (e) of herbicide compounds are compounds that act like the plant hormone auxins such as indole-3-acetic acid. Synthetic auxins belong to group O of the HRAC classification system (see HRAC, Classification of Herbicides According to Mode of Action, http: / / www.plantprotection.org / hrac / MOA.html ).

[0152] Suitable examples of herbicidal compounds of group (e) of auxin herbicides and auxin transport inhibitors include, for example

[0153] Benzoic acid herbicides, such as dicamba, tricamba, chloramben and 2,3,6-TBA (2,3,6-trichlorobenzoic acid) and their salts and esters, for example, dicamba diethanolamine salt, dicamba ethanolamine salt, dicamba N,N-bis-(3-aminopropyl)methylamine salt (dicamba BAPMA salt) and dicamba potassium salt;

[0154] Quinolinecarboxylic acid herbicides, such as quinclorac and quinmerac and their salts and esters, such as quinclorac-dimethylammonium;

[0155] Pyridine carboxylic acid herbicides, such as aminopyralid and its salts (potassium salt, tri(2-hydroxypropyl)ammonium salt, and choline salt), clopyralid and its salts (ethanolamine salt, potassium salt, triethylammonium salt, and choline salt), halauxifen, halauxifen-methyl, florpyrauxifen, florpyrauxifen-benzyl (CAS 1390661-72-9), picloram and its salts (potassium salt, , tris(2-hydroxypropyl)ammonium salt, and choline salt), aminocyclopyrachlor and its salts and esters, triclopyr and its salts or esters (butyryl ester, and triethylammonium salt), and fluroxypyr and its salts and esters, such as aminocyclopyrachlor-dimethylammonium, aminocyclopyrachlor-tris(2-hydroxypropyl)ammonium, fluroxypyr-butometyl and fluroxypyr-meptyl; and

[0156] Phenoxycarboxylic acid herbicides, such as chlorambucil, phenoxyacetic acid herbicides, such as 2,4-D, 3,4-DA, MCPA and its salts or esters (such as dimethylammonium salt, 2-ethylhexyl ester, isooctyl ester, sodium salt, and choline salt), MCPA-thioethyl, 2,4,5-T, phenoxypropionic acid herbicides, such as 2,4-DP (2,4-dichloropropionic acid) and its salts or esters (butyryl ester, dimethylammonium salt, 2-ethylhexyl ester, isooctyl ester, methyl ester, potassium salt, sodium salt, and choline salt), 2,4-DP-P, 2,4-DP-P dimethylammonium, 4-CPP, 3,4-DP, t-propionic acid (fe noprop), CMPP (mecoprop) and its salts or esters (dimethylammonium salt, diethanolamine salt, ethylene glycol ester, 2-ethylhexyl ester, isooctyl ester, methyl ester, potassium salt, sodium salt, triethanolamine salt, and choline salt), CMPP-P (purified mecoprop) and its salts or esters (dimethylammonium salt, 2-ethylhexyl ester, isobutyl salt, potassium salt, and choline salt), and phenoxybutyric acid herbicides such as 4-CPB, 2,4-DB and its salts or esters (such as dimethylammonium salt, isooctyl ester, and choline salt), 3,4-DB, 2,4,5-TB, MCPB, and its salts and esters

[0157] Other herbicides, such as benazolin, benazolin-ethyl, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)picolinic acid (CAS 1629965-65-6), diflufenzopyr, diflufenzopyr-sodium, naptalam and naptalam-sodium.

[0158] The herbicides of group (f) of herbicidal compounds are inhibitors of electron transfer in plant photosynthesis, having a mode of action comprising inhibiting electron transfer in photosystem II of plant photosynthesis. They are also known as PS II inhibitors. They belong to groups C1 to C3 of the HRAC classification system (see HRAC, Classification of herbicides according to mode of action, http: / / www.plantprotection.org / hrac / MOA.html).

[0159] Photosynthesis inhibitors (PS II inhibitors) are known, for example, from the following literature: K.-W. Münks and K.-H. Müller "Photosynthesis Inhibitors", in "Modern Crop Protection Compounds", Volume 1, Wiley-VHC 2007, pages 359-400; CDS Tomlin, "The Pesticide Manual", 13th edition, BCPC (2003) and also The Compendium of Pesticide Common Names, http: / / www.alanwood.net / pesticides / .

[0160] The term photosynthesis inhibitor (PS II inhibitor) is intended in this article to also include the corresponding salts, isomers and esters of the above-mentioned compounds. Suitable salts are, for example, salts of alkali metals or alkaline earth metals or ammonium salts or organic ammonium salts, such as sodium salts, potassium salts, ammonium salts, isopropylammonium, etc. Suitable isomers are, for example, stereoisomers, such as enantiomers. Suitable esters are, for example, C1-C8-(branched or unbranched) alkyl esters, such as methyl esters, ethyl esters and isopropyl esters.

[0161] Suitable examples of herbicidal compounds of group (f) of photosynthesis inhibitors include, for example:

[0162] aryl urea herbicides, for example chlorbromuron, chlorotoluron, chloroxuron, dimefuron, diuron, ethimuron, fenuron, fluometuron, isoproturon, isouron, linuron, bethiazuron, metabethiazuron, metobenzuron, metobromuron, metxuron, monolinuron, neburon, siduron, tetrafluron, tebuthiuron, thiadiazuron and their salts and esters;

[0163] triazine (di)one herbicides, for example ametridione, amibuzin, ethiozin, hexazinone, isomethiozin, metamitron, metribuzin and their salts and esters;

[0164] triazine herbicides, for example chlorotriazine, triazinones, triazindiones, methylthiotriazines, chloridazone, terbuthylazine, trietazin, ametryn, atrazine, aziprotryne, chlorazine, cyanatryn, cyanazine, cyprazine, desmetryn, dimethamet ryn, eglinazine, ipazine, mesoprazine, methoprene, prometryn, procyazine, proglinazine, prometon, propazine, sebuthylazine, simazine, simetryn, terbumeton, terbuthylazine, terbutryn, trietazine and their salts and esters, such as eglinazine-ethyl and ipazine-ethyl;

[0165] · pyridazinone herbicides, for example brompyrazon, chloridazon, dimidazon, metflurazon, norflurazon, oxapyrazon, pydanon and their salts and esters. A preferred pyridazinone herbicide is chloridazon;

[0166] phenylcarbamate herbicides, for example desmedipham, karbutilate, phenisopham, phenmedipham and their salts and esters, such as phenmedipham-ethyl;

[0167] Nitrile herbicides, for example bromobonil, bromofenoxim, bromoxynil, bromoxynil-octanoate, chloroxynil, dichlobenil, iodobonil, ioxynil, ioxynil-octanoate and their salts and esters, in particular bromoxynil, chloroxynil and ioxynil. A preferred nitrile herbicide is bromoxynil;

[0168] benzothiadiazinone herbicides, for example bentazone and its salts, in particular its alkali metal salts, such as bentazone-sodium;

[0169] uracil herbicides, for example bromacil, flupropacil, isocil, lenacil, terbacil and the salts of bromacil, in particular the alkali metal salts thereof, such as bromacil-lithium and bromacil-sodium;

[0170] phenyl-pyridazine herbicides, such as pyridate; and

[0171] Amide herbicides, such as amicarbazone and propanil,

[0172] Other herbicides, such as 1-(6-tert-butylpyrimidin-4-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1654744-66-7), 1-(5-tert-butylisoxazol-3-yl)-2-hydroxy-4-methoxy-3-methyl-2H-pyrrol-5-one (CAS 1637455-12-9), 1-(5-tert-butylisoxazol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS 1637453-94-1), 1-(5-tert-butyl-1-methyl -pyrazol-3-yl)-4-chloro-2-hydroxy-3-methyl-2H-pyrrol-5-one (CAS1654057-29-0), 1-(5-tert-butyl-1-methyl-pyrazol-3-yl)-3-chloro-2-hydroxy-4-methyl-2H-pyrrol-5-one (CAS1654747-80-4), 4-hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS2023785-78-4), 4-hydroxy-1,5-dimethyl-3-[4-(trifluoromethyl)-2- [4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS2023785-79-5), 5-ethoxy-4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS1701416-69-4), 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)-2-pyridyl]imidazolidin-2-one (CAS1708087-22-2), 4-hydroxy-1,5-dimethyl-3-[1-methyl-5-(trifluoromethyl)pyrazol-3-yl]imidazolidin-2-one (CAS2023785-80- 8), 1-(5-tert-butylisoxazol-3-yl)-4-ethoxy-5-hydroxy-3-methyl-imidazolidin-2-one (CAS 1844836-64-1), pyridafol, pentanochlor, diquat, diquat-dibromide, paraquat, paraquat-dichloride and paraquat-dimetilsulfate.

[0173] Among them, aryl urea herbicides are preferred.

[0174] The herbicides of group (g) of herbicidal compounds are inhibitors of lipid biosynthesis (acetyl-CoA carboxylase inhibitors, ACCase inhibitors). They are compounds which have a mode of action which comprises the inhibition of lipid biosynthesis in plants and which belong to group A of the HRAC classification system (see HRAC, Classification of Herbicides According to Mode of Action, http: / / www.plantprotection.org / hrac / MOA.html ).

[0175] Suitable ACCase inhibitors are for example from CDS Tomlin, "The Pesticide Manual", 13th edition, BCPC (2003) and also The Compendium of Pesticide Common Names, http: / / www.alanwood.net / pesticides / known in.

[0176] The term "ACCase inhibitor" is intended to include in this article the corresponding salts, isomers and esters of the above compounds. Suitable salts are, for example, salts of alkali metals or alkaline earth metals or ammonium salts or organic ammonium salts, such as sodium salts, potassium salts, ammonium salts, isopropylammonium, etc. Suitable isomers are, for example, stereoisomers, such as enantiomers. Suitable esters are, for example, propargyl esters, tetrahydrofurfuryl (tefuryl) (tetrahydrofurfuryl (tetrahydrofurfuryl)) esters, ethoxyethyl (etotyl) (ethoxyethyl (ethoxyethyl)) esters, C1-C8- (branched or unbranched) alkyl esters, such as methyl esters, ethyl esters, isopropyl esters, butyl esters and isobutyl esters.

[0177] Suitable ACCase inhibitors of group (g) of herbicide compounds include, for example

[0178] Aryloxyphenoxy-propionate herbicides, such as chlorazifop, clodinafop, clofop, cyhalofop, diclofop, fenoxaprop, fenthiaprop, fluazifop, haloxyfop, isoxapyrifop, kuicaoxi, metamifop, propaquizafop, quizalofop, trifop and their enantiomers, salts and esters, such as fenoxaprop-P, fluazifop-P, haloxyfop-P, quizalofop-P, haloxyfop-sodium, chlorazifop-propargyl, clodinafop-propargyl -propargyl), clofop-isobutyl, cyhalofop-butyl, diclofop-methyl, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenthiaprop-ethyl, fluazifop-methyl, fluazifop-butyl, fluazifop-butyl, haloxyfop-P-butyl, haloxyfop-etotyl, haloxyfop-methyl, haloxyfop-P-etotyl, haloxyfop-P-methyl, quizalofop-ethyl, quizalofop-tefuryl, quizalofop-P-ethyl and quizalofop-P-tefuryl;

[0179] Cyclohexanedione herbicides, such as alloxydim, butroxydim, clethodim, cloproxydim, cycloxydim, profoxydim, sethoxydim, tepraloxydim, tralkoxydim and their salts, such as alloxydim-sodium;

[0180] · phenylpyrazoline herbicides, such as pinoxaden; and

[0181] Unclassified herbicides, such as 4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS1312337-72-6); 4-(2',4'-dichloro-4-cyclopropyl[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3(6H)-one (CAS1312337-45-3); 4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5-hydroxy-2,2,6,6-tetramethyl-2H-pyran-3( 6H)-one (CAS1033757-93-5); 4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-2,2,6,6-tetramethyl-2H-pyran-3,5(4H,6H)-dione (CAS1312340-84-3); 5-(acetyloxy)-4-(4'-chloro-4-cyclopropyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS1312337-48-6); 5-(acetyloxy)-4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)- ]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one; 5-(acetyloxy)-4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS1312340-82-1); 5-(acetyloxy)-4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-3,6-dihydro-2,2,6,6-tetramethyl-2H-pyran-3-one (CAS1033760-55-2); 4-(4'-chloro-4-cyclopropyl-2'-fluoro Methyl [1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonate (CAS1312337-51-1); Methyl 4-(2',4'-dichloro-4-cyclopropyl-[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonate; Methyl 4-(4'-chloro-4-ethyl-2'-fluoro[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonate (CAS1312340-83-2);and methyl 4-(2',4'-dichloro-4-ethyl[1,1'-biphenyl]-3-yl)-5,6-dihydro-2,2,6,6-tetramethyl-5-oxo-2H-pyran-3-yl carbonate (CAS 1033760-58-5), as described in WO 2010 / 136431, WO 2011 / 073615 and WO 2011 / 073616. ;

[0182] Suitable non-ACCase inhibitors of group (h) of the herbicide compounds include, for example, benfuresate, butylate, cycloate, dalapon, pyraclostrobin, EPTC, pentocarb, ethoxyfuroxan, tetrafluoropropionic acid, molinate, orbencarb, pebulate, procarb, TCA, molinate, orbencarb, pebulate, ernolate, and ernolate.

[0183] Suitable herbicide compounds of group (i) include, for example, PDS inhibitors: flubutamide, flufenacet, fluazifop, flurochloridone, flurochloridone, fluthiocarb, flufenacet, 4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethylphenyl)pyrimidine (CAS 180608-33-7), rimisoxafen, HPPD inhibitors: benzobicyclon, benzofenap, flufenacet, clomazone, fenquinone, isoxaflutole, mesotrione, oxotrione (CAS 1486617-21-3), pyrasulfotole, pyrazolamide (pyrazolynate), pyrazoxyfen, sulcotrione, tefuryltrione, tefuryltrione, pyraclostrobin, pyrazone, bipyrazone, fenpyrazone, cypyrafluone, tripyrasulfone, benquitrione, dioxopyritrione; bleaching agents, unknown target: aclonifen, cyproconazole, flumeturon, 2-chloro-3-methylsulfanyl-N-(1-methyltetrazol-5-yl)-4-(trifluoromethyl)benzamide (CAS 1361139-71-0), bixlozone and 2-(2,5-dichlorophenyl)methyl-4,4-dimethyl-3-isoxazolidinone (CAS 81778-66-7).

[0184] Suitable herbicide compounds of group (j) include, for example, the DHP synthase inhibitor: asulam.

[0185] Suitable herbicidal compounds of group (k) include, for example, compounds of group K1: dinitroanilines such as fluazifop, butralin, dimethoate, ethalfluralin, fluchloralin, oryzalin, pendimethalin, prodiamine and trifluralin, phosphamides such as phosphamimid, phosphamimid-methyl and butamiphate. os), benzoic acid herbicides such as chlorthal and chlorthal-dimethyl, pyridines such as dithiopyr and thiamethoxam, benzamides such as propyzamide and tebutam; compounds of group K2: carbetamide, chlorpropamide, chlorpyrifos, chlorpyrifos-isopropyl, chlorpyrifos-methyl, refined chlorpyrifos-isopropyl, refined chlorpyrifos-methyl and chlorpyrifos; among them, compounds of group K1, especially dinitroanilines, are preferred.

[0186] Suitable herbicidal compounds of group (1) include, for example, chloroacetamides such as acetochlor, alachlor, acetamiprid, butachlor, dimethachlor, dimethenamid, dimethenamid, metachlor, metolachlor, S-metolachlor, pethoxamid, pretilachlor, chloranil, propisochlor and thenylchlor, oxyacetanilides such as Flufenacet and mefenacet, acetanilides such as diphenamid, naproxenamide, naproxenamide and dichlorvos, tetrazolinones such as fentrazamide, and other herbicides such as anilofos, cafenstrole, fenoxasulfone, ipfencarbazone, pyroxasulfone, dimethoate and isoxazoline compounds of formula II.1, II.2, II.3, II.4, II.5, II.6, II.7, II.8 and II.9

[0187]

[0188] Isoxazoline compounds of formula (II) are known in the art, for example from WO 2006 / 024820, WO 2006 / 037945, WO 2007 / 071900 and WO 2007 / 096576;

[0189] Among the VLCFA inhibitors, preferred are the chloroacetamides and pyrimidine sulfones.

[0190] Suitable herbicide compounds of group (m) include, for example, chlorthiamid, dichlobenil, flupoxam, indazine fluaziflam, isoxaben, triaziflam and 1-cyclohexyl-5-pentafluorophenoxy-14-[1,2,4,6]thiatriazine-3-ylamine (CAS 175899-01-1).

[0191] Suitable herbicide compounds of group (n) include, for example, dinoseb, dinoterb and DNOC and their salts.

[0192] Suitable herbicides for other herbicides of group (o) are selected from the group consisting of: bromobutyric acid chloranil, chloranil methyl, cyproconazole, benzylpyrasulfuron, cyprosulfuron and its salts and esters, dazomethane, diazepam, diazepam-methyl sulfonate, thiamethoxam, DSMA, cyproconazole, cyprothiocarb and its salts, ethoxybenzamid, chloranil-isopropyl, chloranil-methyl, chloranil-M-isopropyl ... -methyl ester, chlorfenapyr, chlorfenapyr-butyl ester, furapyridine, chlorfenapyr, chlorfenapyr ammonium, indole, maleic hydrazide, fluazifop, metamidine, isoxathiapiprolin, methyl azide, methyl bromide, methyl-chlorfenapyr, methyl iodide, MSMA, oleic acid, oxazithromycin, nonanoic acid, barnyardgrass, chlorfenapyr, tetrafluthrin, chlorfenapyr and 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (CAS 499223-49-3) and its salts and esters, and 6-chloro-4-(2,7-dimethyl-1-naphthyl)-5-hydroxy-2-methyl-pyridazin-3-one (CAS2414510-21-5) (HST inhibitor; FMC).

[0193] In a particular set of embodiments (1), the herbicide compound is selected from the herbicide compounds of group (a), which are particularly selected from the group consisting of glufosinate, glufosinate salts and combinations thereof. In this particular set of embodiments (1), the herbicide of group (a) is the only herbicide.

[0194] In a subgroup (1.1) of embodiment group (1), the herbicide compound is selected from the racemic glufosinate mixture as described above, wherein the glufosinate comprises about 50% by weight of the L-enantiomer and about 50% by weight of the D-enantiomer. In another subgroup (1.2) of embodiment group (1), the herbicide compound is glufosinate, wherein at least 70% by weight of the glufosinate is L-glufosinate or a salt thereof, in particular L-glufosinate ammonium.

[0195] In a specific group of embodiments (2), the herbicide compound is selected from a combination of a herbicide compound of group (a) and at least one additional herbicide compound selected from a herbicide compound of one of groups (b) to (o), particularly preferably a herbicide of groups (b), (c), (d), (e), (f), (g), (i), (l), (m) and (o).

[0196] In a specific subgroup (2.b) of embodiment group (2), the herbicide compound is selected from a combination of a herbicide compound of group (a) and at least one additional herbicide compound selected from a herbicide compound of group (b). In this subgroup (2.b), the herbicide (b) is in particular glyphosate or a salt thereof.

[0197] In a specific subgroup (2.c) of embodiment group (2), the herbicide compound is selected from a combination of a herbicide compound of group (a) and at least one further herbicide compound selected from a herbicide compound of group (c). In this subgroup (2.c), the herbicide (c) is in particular selected from the class of imidazolinones. Particularly preferred herbicides (c) are imazamox, imazapic, imazapic and methyl imazapic and their salts.

[0198] In a specific subgroup (2.d) of embodiment group (2), the herbicide compound is selected from a combination of a herbicide compound of group (a) and at least one additional herbicide compound selected from a herbicide compound of group (d). In this subgroup (2.d), the herbicide (d) is particularly selected from the group consisting of: saflufenacil, trifluoxetine, fluazifop-butyl, sulfentrazone, fluazifop-butyl, fluazifop-butyl, fluazifop-butyl, 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]-acetic acid methyl ester (CAS 2158274-96-3), 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]-acetic acid methyl ester (CAS 2158274-96-3), 2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]acetic acid methyl ester (CAS2158275-73-9), 2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6 -dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]ethyl acetate (CAS2158274-56-5), 2-[2-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]-N-(methylsulfonyl)acetamide (CAS2158274-53-2), 2-[[3-[[3-chloro-6-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]phenoxy]-N-(methylsulfonyl)acetamide [dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-5-fluoro-2-pyridinyl]oxy]-2-pyridinyl]oxy]-N-(methylsulfonyl)acetamide (CAS2158276-22-1), 3-[2-chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluorophenyl]-4,5-dihydro-5-methyl-5-isoxazolecarboxylic acid ethyl ester (CAS1949837-17-5) and mixtures thereof.

[0199] In a specific subgroup (2.e) of embodiment group (2), the herbicide compound is selected from a combination of a herbicide compound of group (a) and at least one additional herbicide compound selected from a herbicide compound of group (e). In this subgroup (2.e), the herbicide (e) is particularly selected from the group consisting of: dicamba and its salts, such as dicamba diethanolamine salt, dicamba ethanolamine salt, dicamba N,N-bis-(3-aminopropyl)methylamine salt (dicamba BAPMA salt) and dicamba potassium salt, cypermethrin and its salts, such as cypermethrin-dimethylammonium, fluclopyridin-methyl, cypermethrin-methyl, cypermethrin-benzyl (CAS1390661-72-9), 2,4-D and its salts or esters, such as choline salts; and mixtures thereof.

[0200] In a specific subgroup (2.f) of embodiment group (2), the herbicide compound is selected from a combination of a herbicide compound of group (a) and at least one additional herbicide compound selected from a herbicide compound of group (f). In this subgroup (2.f), the herbicide (f) is particularly selected from the group consisting of diuron, fluometuron, thidiazuron, metribuzin, atrazine, prometryn and mixtures thereof.

[0201] In a specific subgroup (2.g) of embodiment group (2), the herbicide compound is selected from a combination of a herbicide compound of group (a) and at least one additional herbicide compound selected from a herbicide compound of group (g). In this subgroup (2.g), the herbicide (g) is in particular clethodim.

[0202] In a specific subgroup (2.i) of embodiment group (2), the herbicide compound is selected from a combination of a herbicide compound of group (a) and at least one additional herbicide compound selected from a herbicide compound of group (i). In this subgroup (2.i), the herbicide (i) is particularly selected from difluanid, flupyralid, flupyralid, clomazone, isoxaflutole, mesotrione, cypermethrin, pyraclostrobin, cypermethrin, cypermethrin-butyl, benfenac, clomazone and mixtures thereof.

[0203] In a specific subgroup (2.1) of embodiment group (2), the herbicide compound is selected from a combination of a herbicide compound of group (a) and at least one additional herbicide compound selected from a herbicide compound of group (1). In this subgroup (2.1), the herbicide (1) is particularly selected from acetochlor, dimethinamid, dimethinamid-S, pyraclostrobin, isopropyl metolachlor, isopropyl metolachlor, pethodiamide, pyrimidine and mixtures thereof.

[0204] In a specific subgroup (2.m) of embodiment group (2), the herbicide compound is selected from a combination of a herbicide compound of group (a) and at least one additional herbicide compound selected from a herbicide compound of group (m). In this subgroup (2.m), the herbicide (m) is particularly selected from indazine fluazifop and triazine fluazifop and mixtures thereof.

[0205] In a specific subgroup (2.o) of group (2) of the embodiments, the herbicide compound is selected from a combination of a herbicide compound of group (a) and at least one additional herbicide compound selected from a herbicide compound of group (o). In this subgroup (2.o), the herbicide (o) is particularly selected from cyproconazole and tetrafluanid and mixtures thereof.

[0206] In embodiment group (2) and also in subgroups (2.b) to (2.o) of the embodiments, the herbicide of group (a) is in particular chosen from the group consisting of glufosinate, glufosinate salts and combinations thereof.

[0207] In a subgroup (2.1) of embodiment group (2), the herbicide compound is more particularly selected from the racemic glufosinate mixture as described above, wherein the glufosinate comprises about 50% by weight of the L-enantiomer and about 50% by weight of the D-enantiomer. In another subgroup (2.2) of embodiment group (2), the herbicide compound is glufosinate, wherein at least 70% by weight of the glufosinate is L-glufosinate or a salt thereof, in particular L-glufosinate ammonium.

[0208] In the embodiment groups (1) and (2), and also in the subgroups (1.1), (1.2), (2.b), (2.c), (2.d), (2.e), (2.f), (2.g), (2.i), (2.l), (2.m) and (2.o) of the embodiments, the herbicide compound (a) is in particular selected from the group consisting of sodium, potassium or ammonium glufosinate and L-glufosinate (NH4 + ) salts, in particular glufosinate-ammonium and L-glufosinate-ammonium.

[0209] In embodiment group (2), the relative weight ratio of the herbicide compound (a) to the additional herbicide is preferably in the range of 1:10 to 1000:1, particularly in the range of 1:5 to 500:1 and more preferably in the range of 1:1 to 1:250.

[0210] In the methods according to the invention and also in the uses according to the invention, the alkyl ether sulfates of formula (I) and the one or more herbicidal compounds can be formulated into a single formulation, or they can be used in separate formulations.

[0211] Herbicidal formulations comprising at least one alkyl ether sulfate of formula (I) and at least one herbicide compound as defined herein, in particular a herbicide compound of groups (a) to (o) of the herbicides, are novel and are therefore a further aspect of the present invention.

[0212] In the formulations of the present invention, with respect to the variable M in formula (I) + Any statements of preferred meanings of and n and combinations thereof apply in the same manner as given above.

[0213] With regard to herbicides, the preferences given above also apply to these formulations. In particular, the formulations of the invention comprise at least one alkyl ether sulfate of formula (I) and at least one herbicide compound according to embodiment group (1) or (2). More particularly, the formulations of the invention comprise at least one herbicide compound of group (a), which is particularly selected from glufosinate and its salts, and optionally at least one additional herbicide selected from the herbicides of groups (b) to (o) as defined above.

[0214] In particular, the herbicide compound of group (a) of the herbicidal formulation of the present invention comprises a glufosinate salt selected from the group consisting of sodium, potassium and ammonium glufosinate (NH4 + )Salt.

[0215] In particular, the herbicide compound of group (a) of the herbicidal formulations according to the invention is an L-glufosinate salt, which is in particular selected from the group consisting of sodium, potassium and ammonium (NH4) L-glufosinate. + )Salt.

[0216] According to a particular set of embodiments, the herbicide compound of group (a), in particular chosen from glufosinate and its salts, is the only herbicide comprised in the formulation.

[0217] According to another particular group of embodiments, the formulation contains a herbicide compound of group (a), in particular chosen from glufosinate and its salts, and at least one additional herbicide compound chosen from groups (b) to (o) of herbicide compounds as defined above.

[0218] Furthermore, the herbicidal formulations according to the invention or the aqueous spray liquids according to the invention may contain water and an organic solvent, as described above. Examples of suitable organic solvents are as described above. The concentrations of water and organic solvents are also as described above.

[0219] In these herbicide formulations, the weight ratio of alkyl ether sulfate of formula (I) to herbicide compound is preferably in the range from 1:10 to 10:1, in particular in the range from 1:5 to 7:1 and especially in the range from 1:1 to 6:1.

[0220] In the formulations according to the invention, the concentration of the alkyl ether sulfate of formula (I) is generally in the range from 5 to 60% by weight, in particular in the range from 10 to 50% by weight, based on the total weight of the formulation.

[0221] In the formulations of the present invention, the concentration of the herbicide compound is generally in the range of 1 to 60% by weight, in particular in the range of 5 to 50% by weight, based on the total weight of the formulation.

[0222] In addition to the alkyl ether sulfate having formula (I) and the herbicide compound or mixture of herbicide compounds, the formulations of the present invention may also contain conventional formulation adjuvants, including solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesives, thickeners, wetting agents, antifreeze agents, defoamers, colorants, crystal growth inhibitors, tackifiers and adhesives.

[0223] Suitable surfactants include, but are not limited to, aromatic sulfonic acids (e.g. lignin-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acids) and also alkali metal salts, alkaline earth metal salts, ammonium salts of fatty acids, alkyl- and alkylarylsulfonates, alkyl-, lauryl ether and fatty alcohol sulfates and also sulfated salts of hexa-, hepta- and octadecyl alcohols and fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene and naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ethers, ethoxylated isooctyl, octyl or nonylphenol, alkylphenyl, tributylphenyl polyglycol ethers, alkylaryl polyether alcohols, isotridecanol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetates, sorbitol esters, lignin sulfite waste liquor or methylcellulose.

[0224] Suitable liquid carriers include water and organic solvents. Suitable organic solvents are aliphatic hydrocarbons, preferably aliphatic C5-C 16 - hydrocarbons, more preferably C5-C 16 -alkanes, or C5-C 16 - cycloalkanes, such as pentane, hexane, cyclohexane, or petroleum ether; aromatic hydrocarbons, preferably aromatic C6-C 10 - hydrocarbons, such as benzene, toluene, o-xylene, m-xylene and p-xylene; halogenated hydrocarbons, preferably halogenated aliphatic C1-C6-alkanes, or halogenated aromatic C6-C 10 - hydrocarbons, such as CH2Cl2, CHCl3, CCl4, CH2ClCH2Cl, CCl3CH3, CHCl2CH2Cl, CCl2CCl2, or chlorobenzene; ethers, preferably C1-C6-cycloalkyl ethers, C1-C6-alkyl-C1-C6-alkyl ethers and C1-C6-alkyl-C6-C10 - aryl ethers, such as CH3CH2OCH2CH3, (CH3)2CHOCH(CH3)2, CH3OC(CH3)3(MTBE), CH3OCH3(DME), CH3OCH2CH2OCH3, dioxane, anisole, and tetrahydrofuran (THF); esters, preferably esters of aliphatic C1-C6-alcohols and aliphatic C1-C6-carboxylic acids, aromatic C6-C 10 -Alcohols and aromatic C6-C 10 -carboxylic acid esters, cyclic esters of ω-hydroxy-C1-C6-carboxylic acids, such as CH3C(O)OCH2CH3, CH3C(O)OCH3, CH3C(O)OCH2CH2CH2CH3, CH3C(O)OCH(CH3)CH2CH3, CH3C(O)OC(CH3), CH3CH2CH2C(O)OCH2CH3, CH3CH(OH)C(O)OCH2CH3, CH3CH(OH)C (O)OCH3, CH3C(O)OCH2CH(CH3)2, CH3C(O)OCH(CH3)2, CH3CH2C(O)OCH3, benzyl benzoate, and γ-butyrolactone; carbonates such as ethylene carbonate, propylene carbonate, CH3CH2OC(O)OCH2CH3, and CH3OC(O)OCH3; nitriles, preferably C1-C6-nitriles, such as CH3CN, and CH3CH2CN; ketones, preferably C1-C6-nitriles, such as CH3CN, and CH3CH2CN; C6-alkyl-C1-C6-alkyl ketones, such as CH3C(O)CH3, CH3C(O)CH2CH3, CH3CH2C(O)CH2CH3, and CH3C(O)C(CH3)3 (MTBK); alcohols, preferably C1-C4-alcohols, such as CH3OH, CH3CH2OH, CH3CH2CH2OH, CH3CH(OH)CH3, CH3(CH2)3OH, C(CH3)3OH, propylene glycol, diol Propylene glycol, propylene glycol monomethyl ether (1-methoxy-2-propanol); amide and urea derivatives, preferably dimethylformamide (DMF), N-methyl-2-pyrrolidone (NMP), dimethylacetamide (DMA), 1,3-dimethyl-2-imidazolidinone (DMI), 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU), hexamethylphosphoramide (HMPA); in addition, dimethyl sulfoxide (DMSO), and cyclopentane. Preferred solvents are propylene glycol, dipropylene glycol and propylene glycol monomethyl ether, more preferably propylene glycol and dipropylene glycol.

[0225] Solid carriers are mineral earths, such as silica, silica gel, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfates, magnesium oxide, ground plastics, fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, and plant products, such as grain flour, bark flour, wood flour and nut shell flour, cellulose powder, or other solid carriers.

[0226] Suitable surfactants are surface-active compounds such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof, wherein such surfactants are not alkyl ether sulfates having formula (I). Such surfactants can be used as emulsifiers, dispersants, solubilizers, wetting agents, penetration enhancers, protective colloids, or adjuvants. Examples of surfactants are listed in McCutcheon's, Vol. 1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International or North American Edition).

[0227] Suitable anionic surfactants are alkali metal salts, alkaline earth metal salts or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. The example of sulfonates is alkyl aryl sulfonates, diphenyl sulfonates, α-olefin sulfonates, lignin sulfonates, fatty acids and oily sulfonates, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalene, dodecyl- and tridecylbenzene sulfonates, sulfonates of naphthalene and alkylnaphthalene, sulfosuccinates or sulfosuccinamates. The example of sulfate is the sulfate of fatty acids and oily sulfates, ethoxylated alkylphenol sulfates, sulfates of alcohols, sulfates of ethoxylated alcohols (except those with formula (I)), or sulfates of fatty acid esters. The example of phosphate is phosphate ester. The example of carboxylates is alkyl carboxylates and carboxylated alcohols or alkylphenol ethoxylates.

[0228] Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, surfactants based on sugars, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters that have been alkoxylated by 1 to 50 equivalents. Oxyethylene oxide and / or propylene oxide can be used for alkoxylation, preferably ethylene oxide. Examples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerides or monoglycerides. Examples of surfactants based on sugars are sorbitan, ethoxylated sorbitan, sucrose and glucose esters or alkyl polyglucosides. Examples of polymeric surfactants are homopolymers or copolymers of vinyl pyrrolidone, vinyl alcohol or vinyl acetate.

[0229] Suitable cationic surfactants are quaternary ammonium surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups or salts of long-chain primary amines. Suitable amphoteric surfactants are alkyl betaines and imidazolines. Suitable block polymers are AB or ABA type block polymers comprising blocks of polyethylene oxide and polypropylene oxide, or ABC type block polymers comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polyalkalis. The example of polyacids is the alkali metal salt of polyacrylic acid or polyacid comb-like polymers. The example of polyalkalis is polyvinylamine or polyvinylamine.

[0230] Suitable thickeners are polysaccharides (e.g., xanthan gum, carboxymethyl cellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates. Suitable bactericides are bronopol and isothiazolinone derivatives, such as alkylisothiazolinone and benzisothiazolinone. Suitable antifreeze agents are ethylene glycol, propylene glycol, urea, and glycerol. Suitable defoamers are salts of silicone, long-chain alcohols, and fatty acids. Suitable colorants (e.g., red, blue, or green) are low water-soluble pigments and water-soluble dyes. Examples are inorganic colorants (e.g., iron oxide, titanium oxide, hexacyanoferrate) and organic colorants (e.g., alizarin colorants, azo colorants, and phthalocyanine colorants). Suitable tackifiers or adhesives are polyvinyl pyrrolidone, polyvinyl acetate, polyvinyl alcohol, polyacrylates, biological or synthetic waxes, and cellulose ethers.

[0231] The formulations according to the invention are prepared in a known manner, as described, for example, by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, Agrow Reports DS 243, T&F Informa, London, 2005.

[0232] The formulation type of the formulation of the present invention is secondary and will depend on the herbicide compound in a known manner. Basically, formulations containing herbicide compounds and alkyl ether sulfates with formula (I) can be easily diluted with water. Suitable formulations of herbicide active ingredients include, but are not limited to, water-soluble concentrates (SL or LS formulations), dispersible concentrates (DC formulations), emulsifiable concentrates (EC formulations), emulsions (EW, EO or ES formulations), can be water-based or oil-based suspension concentrates (SC, OD or FS formulations), microemulsions (ME formulations), microcapsule formulations (CS formulations), wettable powders or dusts (e.g., WP, SP, WS, DP, DS), wettable granules (e.g., WG, SG, GR, FG, GG, MG) and the like. These and additional composition types are defined in "Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 6th edition May 2008, CropLife International.

[0233] Preferably, the herbicidal formulations according to the invention are liquid formulations, in particular soluble liquid (SL) formulations. If the formulations according to the invention contain a herbicide from group (a), they are in particular an aqueous solution or a soluble liquid of the corresponding herbicide (a) and an alkyl ether sulfate of formula (I). In particular, the alkyl ether sulfate of formula (I) contained in the formulations according to the invention is an ammonium salt of 2-propylheptyl ether sulfate or isodecyl ether sulfate, wherein M + Yes H 4-m NR 1 m + , where R 1is as defined above and in particular selected from the group consisting of unbranched or branched alkyl having preferably 1 to 4 carbon atoms, OH-substituted alkyl having preferably 2 to 4 carbon atoms, such as CH2CH2OH and CH2CH(OH)CH3, and m is an integer in the range of 1 to 4, in particular 1, 2 or 3, wherein the variable n is preferably in the range of 1 to 5, in particular in the range of 1 to 3, in particular n is 2, and wherein the average value of n is preferably in the range of 1.1 to 5.0, in particular in the range of 1.5 to 4.5 and in particular in the range of 1.7 to 3.5.

[0234] The herbicidal formulations according to the invention may also be aqueous suspension concentrates (SC). In such suspension concentrates, the active substance is present in finely divided particulate form, i.e. in a form in which the active substance is present as particles suspended in an aqueous phase. The diameter of the active substance particles will generally not exceed 50 μm. In particular, at least 90% by weight of the active substance particles will have a diameter below 30 μm, in particular below 20 μm. Advantageously, at least 40% by weight and in particular at least 60% by weight of the particles in the SC according to the invention have a diameter below 5 μm.

[0235] The SC formulation of the present invention (hereinafter SC) comprises an alkyl ether sulfate having formula (I) and one or more herbicide compounds, in particular glufosinate or a salt thereof.

[0236] Preferably, the alkyl ether sulfate of formula (I) contained in SC is an ammonium salt of 2-propylheptyl ether sulfate or isodecyl ether sulfate, wherein M + Yes H 4-m NR 1 m + , where R 1 is as defined above and in particular selected from the group consisting of unbranched or branched alkyl having preferably 1 to 4 carbon atoms, OH-substituted alkyl having preferably 2 to 4 carbon atoms, such as CH2CH2OH and CH2CH(OH)CH3, and m is an integer in the range of 1 to 4, in particular 1, 2 or 3, wherein the variable n is preferably in the range of 1 to 5, in particular in the range of 1 to 3, in particular n is 2, and wherein the average value of n is preferably in the range of 1.1 to 5.0, in particular in the range of 1.5 to 4.5 and in particular in the range of 1.7 to 3.5.

[0237] The amount of active substances in such SCs, i.e. the total amount of one or more herbicidal compounds, in particular at least one herbicidal compound from groups (a) to (o), preferably a herbicide compound from group (a), in particular selected from glufosinate and its salts, and, if appropriate, one or more further active substances selected from groups (b) to (o) of herbicidal compounds as defined above, based on the total weight of the suspension concentrate, is generally in the range from 5 to 60% by weight, in particular in the range from 10 to 50% by weight.

[0238] The amount of alkyl ether sulfate of the formula (I) in such SCs is generally in the range from 1 to 50% by weight, in particular in the range from 5 to 40% by weight, based on the total weight of the suspension concentrate.

[0239] In addition to the alkyl ether sulfates of formula (I), the aqueous suspension concentrates may also comprise surface-active substances other than those of formula (I) and, if appropriate, one or more auxiliaries, such as defoamers, thickeners, antifreeze agents, stabilizers (biocides), pH regulators and anticaking agents.

[0240] Suitable surfactants other than those of formula (I) are preferably anionic and nonionic surfactants. Other suitable surfactants other than those of formula (I) are protective colloids. Typically, the amount of surfactants other than those of formula (I) will amount to 0 to 30% by weight, in particular 0 to 20% by weight, based on the total weight of the aqueous SC according to the invention. If the surfactants other than those of formula (I) comprise at least one anionic surfactant other than those of formula (I) and at least one nonionic surfactant, the weight ratio of anionic surfactant to nonionic surfactant is typically in the range of 10:1 to 1:10.

[0241] Examples of anionic surface-active substances (surfactants) other than those of the formula (I) include alkylarylsulfonates, phenylsulfonates, alkyl sulfates, alkylsulfonates, alkyl ether sulfates other than those of the formula (I), alkylaryl ether sulfates, alkyl polyglycol ether phosphates, polyarylphenyl ether phosphates, alkyl sulfosuccinates, olefinsulfonates, paraffinsulfonates, petroleum sulfonates, taurates, sarcosinolates, fatty acids, alkylnaphthalenesulfonic acids, naphthalenesulfonic acid, ligninsulfonic acid, condensates of sulfonated naphthalene with formaldehyde or with formaldehyde and phenol and, if appropriate, urea, and condensates of phenolsulfonic acid, formaldehyde and urea, ligninsulfite waste liquors and ligninsulfonates, alkyl phosphates, alkylaryl phosphates, for example tristyryl phosphate, and also polycarboxylates, such as, for example, polyacrylates, maleic anhydride / olefin copolymers (for example CP9, BASF), including alkali metal salts, alkaline earth metal salts, ammonium salts and amine salts of the above substances. Preferred anionic surface-active substances other than those of formula (I) are those containing at least one sulfonate group, and in particular their alkali metal salts and their ammonium salts.

[0242] Examples of nonionic surfactants include alkylphenol alkoxylates, alcohol alkoxylates, fatty amine alkoxylates, polyoxyethylene glycerol fatty acid esters, castor oil alkoxylates, fatty acid alkoxylates, fatty acid amide alkoxylates, fatty acid polydiethanolamides, lanolin ethoxylates, fatty acid polyethylene glycol esters, isotridecanol, fatty acid amides, methylcellulose, fatty acid esters, alkyl polyglycosides, glycerol fatty acid esters, polyethylene glycol, polypropylene glycol, polyethylene glycol / polypropylene glycol block copolymers, polyethylene glycol alkyl ethers, polypropylene glycol alkyl ethers, polyethylene glycol / polypropylene glycol ether block copolymers (polyethylene oxide / polypropylene oxide block copolymers) and mixtures thereof. Preferred nonionic surfactants are fatty alcohol ethoxylates, alkyl polyglycosides, glycerol fatty acid esters, castor oil alkoxylates, fatty acid alkoxylates, fatty acid amide alkoxylates, lanolin ethoxylates, fatty acid polyethylene glycol esters and ethylene oxide / propylene oxide block copolymers, and mixtures of these.

[0243] Protective colloids are typically water-soluble amphiphilic polymers. Examples are proteins and denatured proteins such as casein, polysaccharides such as water-soluble starch derivatives and cellulose derivatives, in particular hydrophobically modified starches and celluloses, furthermore polycarboxylates such as polyacrylic acid and acrylic acid copolymers, polyvinyl alcohol, polyvinylpyrrolidone, vinylpyrrolidone copolymers, polyvinylamine, polyethyleneimines, and polyalkylene ethers.

[0244] Suitable viscosity-modifying additives (thickeners) for the aqueous SC according to the invention are in particular compounds which impart a modified flow behavior to the formulation (e.g. high viscosity in the static state and low viscosity in the moving state). Suitable compounds are in principle all those which are used for this purpose in suspension concentrates. Mentioned substances are, for example, inorganic substances, for example phyllosilicates and organically modified phyllosilicates such as bentonites or attapulgites (e.g. Siloxane from Engelhardt). ), and organic substances such as polysaccharides and heteropolysaccharides such as Xanthan (From Kelco ), 23 (Rhone Poulenc) or (from RT Vanderbilt), wherein Xanthan- The amount of viscosity modifying additives is often from 0 to 7% by weight, based on the total weight of the SC.

[0245] Suitable defoamers for the aqueous SC according to the invention are, for example, the silicone emulsions known for this purpose (SILOX® from Wacker). SRE or from Rhodia ), long-chain alcohols, fatty acids and their salts, defoamers of aqueous wax dispersion type, solid defoamers (called compounds), organic fluorine compounds and mixtures of these. The amount of defoamer is typically 0 to 1.5% by weight based on the total weight of SC.

[0246] Preservatives may also be added to the suspension concentrates according to the invention for the purpose of stabilizing them. Suitable preservatives are those based on isothiazolones, for example the ANTIBASE® from ICI or from ThorChemie RS or from Rohm & Haas MK. The amount of preservative is typically 0 to 0.5% by weight, based on the total weight of SC.

[0247] Suitable antifreeze agents are liquid polyols, for example ethylene glycol, propylene glycol or glycerol, and also urea. The amount of antifreeze agent is generally 0 to 20% by weight, in particular 5 to 10% by weight, based on the total weight of the aqueous suspension concentrate.

[0248] If appropriate, the aqueous SC according to the invention may contain buffers to adjust the pH. Examples of buffers are alkali metal salts of weak inorganic or organic acids such as, for example, phosphoric acid, boric acid, acetic acid, propionic acid, citric acid, fumaric acid, tartaric acid, oxalic acid and succinic acid.

[0249] The herbicidal formulations according to the invention may also be oil dispersions (OD). In such oil dispersions, the active substance is present in the form of finely divided particles, i.e. in a form in which the active substance is present as particles dispersed in an oil phase. The diameter of the active substance particles will generally not exceed 50 μm. In particular, at least 90% by weight of the active substance particles will have a diameter below 30 μm, in particular below 20 μm. Advantageously, at least 40% by weight and in particular at least 60% by weight of the particles in the OD according to the invention have a diameter below 10 μm.

[0250] The OD formulations of the present invention (hereinafter OD) comprise an alkyl ether sulfate having formula (I) and one or more herbicide compounds, in particular glufosinate or a salt thereof.

[0251] Preferably, the alkyl ether sulfate of formula (I) contained in OD is an ammonium salt of 2-propylheptyl ether sulfate or isodecyl ether sulfate, wherein M + Yes H 4-m NR 1 m + , where R 1 is as defined above and in particular selected from the group consisting of unbranched or branched alkyl having preferably 1 to 4 carbon atoms, OH-substituted alkyl having preferably 2 to 4 carbon atoms, such as CH2CH2OH and CH2CH(OH)CH3, and m is an integer in the range of 1 to 4, in particular 1, 2 or 3, wherein the variable n is preferably in the range of 1 to 5, in particular in the range of 1 to 3, in particular n is 2, and wherein the average value of n is preferably in the range of 1.1 to 5.0, in particular in the range of 1.5 to 4.5 and in particular in the range of 1.7 to 3.5.

[0252] The amount of active substances in such ODs, i.e. the total amount of one or more herbicidal compounds, in particular at least one herbicidal compound from groups (a) to (o), preferably a herbicide compound from group (a), which is particularly selected from glufosinate-ammonium and its salts, and, if appropriate, one or more further active substances selected from groups (b) to (o) of herbicidal compounds as defined above, is generally in the range from 5 to 60% by weight, in particular in the range from 10 to 50% by weight, based on the total weight of the oil dispersion.

[0253] The amount of alkyl ether sulfate of formula (I) in such OD is generally in the range from 1 to 45% by weight, in particular in the range from 5 to 40% by weight, based on the total weight of the oil dispersion.

[0254] In addition to the alkyl ether sulfates of formula (I), the oil dispersions may also comprise surface-active substances other than those of formula (I) and, if appropriate, one or more auxiliaries, such as defoamers, thickeners, stabilizers (biocides), pH regulators and anticaking agents.

[0255] Suitable surfactants other than those of formula (I) are preferably the above-mentioned anionic and nonionic surfactants. Typically, the amount of surfactant other than those of formula (I) will amount to 0 to 30% by weight, in particular 0 to 20% by weight, based on the total weight of the OD according to the invention. If the surfactants other than those of formula (I) comprise at least one anionic surfactant other than those of formula (I) and at least one nonionic surfactant, the weight ratio of anionic surfactant to nonionic surfactant is typically in the range of 10:1 to 1:10.

[0256] The herbicidal formulations according to the invention may be a physical mixture of at least one alkyl ether sulfate of formula (I) and at least one herbicide compound as defined herein. However, the formulations may also be any desired combination of an alkyl ether sulfate of formula (I) and at least one herbicide compound, wherein the alkyl ether sulfate of formula (I) and the herbicide compound must not be formulated together.

[0257] An example of a herbicidal formulation according to the invention is a two-component kit in which at least one alkyl ether sulfate of formula (I) and at least one herbicide compound are not formulated together. Therefore, the present invention also provides a two-component kit comprising a first component comprising an alkyl ether sulfate of formula (I), and a second component comprising at least one herbicide compound, a liquid or solid carrier and optionally at least one surfactant and / or at least one conventional adjuvant.

[0258] In the method of the invention, an alkyl ether sulfate of formula (I) and at least one herbicide compound are applied to the undesirable vegetation or its habitat. The order in which the alkyl ether sulfate of formula (I), the one or more herbicidal compounds and, if present, the further herbicide are applied is secondary. It is essential that the alkyl ether sulfate of formula (I) and the one or more herbicidal compounds are present at the site of action at the same time, i.e., are in contact with the plant to be controlled or are taken up by the plant at the same time.

[0259] As mentioned above, the alkyl ether sulfate of formula (I) and at least one herbicide can be co-formulated or separately formulated. In the latter case, the alkyl ether sulfate of formula (I) and at least one herbicide are typically applied as an aqueous spray liquid. Therefore, the present invention also relates to an aqueous spray liquid comprising

[0260] i. at least one alkyl ether sulfate having formula (I) as defined herein; and

[0261] ii. at least one herbicide compound as defined herein.

[0262] For this purpose, the alkyl ether sulfate of formula (I) and the herbicide or a suitable formulation thereof are typically mixed with the application water (make-up water) before applying the combination, ie the herbicide and the alkyl ether sulfate of formula (I) are tank mixed.

[0263] The concentration of the alkyl ether sulfate of formula (I) in the spray liquor depends on the application rate, which is typically in the range of 10 g / ha to 2 kg / ha, in particular in the range of 20 g / ha to 1.5 kg / ha, in particular in the range of 25 g / ha to 1.2 kg / ha, as the free acid (M +=H). The concentration of the alkyl ether sulfate of formula (I) in the aqueous spray liquid is generally in the range of 10 to 150,000 ppm, in particular in the range of 10 to 100,000 ppm, and in particular in the range of 10 to 50,000 ppm, based on the total weight of the aqueous spray liquid, as the free acid (M + =H). The concentration of the herbicide compound in the aqueous spray liquor depends on its application rate, which is typically in the range of 10 g / ha to 1.2 kg / ha, in particular in the range of 20 g / ha to 1.0 kg / ha, in particular in the range of 25 g / ha to 0.8 kg / ha, calculated as active herbicide compound.

[0264] The amount of water applied per hectare is usually in the range of 50 to 1000 l / ha.

[0265] The aqueous spray liquid may have any pH value acceptable for agricultural purposes. Preferably, the aqueous spray liquid has a pH value as measured at 25°C in the range of 4 to 9, in particular in the range of 5 to 8, in particular in the range of 5.5 to 7.5.

[0266] In addition to water, alkyl ether sulfates of formula (I) and herbicides (including herbicide active ingredients and optionally formulation adjuvants), the aqueous spraying liquid may also contain one or more additional agriculturally active ingredients. Additional agriculturally active ingredients may be selected from fungicides, insecticides, nematicides, safeners, fertilizers, micronutrients, biocides, nitrification inhibitors, urease inhibitors, and / or growth regulators. The combination of herbicides and safeners may be particularly useful. Suitable safeners include (quinolin-8-oxy)acetic acid, 1-phenyl-5-haloalkyl-1H-1,2,4-triazole-3-carboxylic acid, 1-phenyl-4,5-dihydro-5-alkyl-1H-pyrazole-3,5-dicarboxylic acid, 4,5-dihydro-5,5-diaryl-3-isoxazolecarboxylic acid, dichloroacetamide, α-oximinophenylacetonitrile, acetophenone oxime, 4,6-dihalo-2-phenylpyrimidine, N-[[4-(aminocarbonyl)phenyl]sulfonyl]-2-benzamide, 1,8-naphthalene dicarboxylic anhydride, 2-halo-4-(haloalkyl)-5-thiazolecarboxylic acid, thiophosphates and N-alkyl-O-phenylcarbamates and agriculturally acceptable salts thereof and agriculturally acceptable derivatives thereof, such as amides, esters, and thioesters, provided that they have an acid group.

[0267] Aqueous spray solutions containing a herbicide and an alkyl ether sulfate of formula (I) are used to control undesirable vegetation on crop areas and non-crop areas.

[0268] Aqueous sprays allow very efficient control of undesirable vegetation on non-crop areas and in crops. In non-crop areas, very effective control is achieved at high application rates. Depending on the herbicide active compound, the application of the spray allows effective control of broadleaf weeds and grass weeds in crops such as wheat, rice, corn, soybeans and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low application rates.

[0269] Spraying liquid is usually applied to undesirable plants mainly by spraying leaves. Here, application can be carried out by conventional spraying technology using about 10 to 1000l / ha of spraying liquid. The application of spraying liquid can be carried out before, during and / or after the emergence of undesirable plants.

[0270] Preferably, in the herbicidal formulations or aqueous spray liquids according to the invention, the weight ratio of alkyl ether sulfate of formula (I) to herbicide compound is preferably in the range of 1:10 to 10:1, in particular in the range of 1:5 to 7:1 and especially in the range of 1:1 to 6:1.

[0271] Also preferably, the herbicide compound of the herbicidal formulation or aqueous spray liquid according to the invention is selected from at least one herbicide compound of groups (a) to (o):

[0272] (a) herbicidal compounds from the group of glutamine synthetase inhibitors;

[0273] (b) herbicidal compounds from the group of enolpyruvylshikimate 3-phosphate synthase inhibitors (EPSP inhibitors);

[0274] (c) herbicidal compounds from the group of acetolactate synthase inhibitors (ALS inhibitors);

[0275] (d) herbicidal compounds from the group of protoporphyrinogen-IX oxidase inhibitors;

[0276] (e) herbicidal compounds from the group of auxin herbicides and auxin transport inhibitors;

[0277] (f) herbicide compounds from the group of photosynthesis inhibitors;

[0278] (g) herbicidal compounds from the group of lipid biosynthesis inhibitors (acetyl-CoA carboxylase inhibitors, ACCase inhibitors);

[0279] (h) lipid biosynthesis inhibitors other than ACCase inhibitors;

[0280] (i) bleaching agent herbicides;

[0281] (j) 7,8-dihydropteroate synthase inhibitors (DHP inhibitors);

[0282] (k) mitotic inhibitors;

[0283] (l) Very long chain fatty acid synthesis inhibitors (VLCFA inhibitors);

[0284] (m) cellulose biosynthesis inhibitors;

[0285] (n) Decoupler herbicides;

[0286] (o) other herbicides selected from the group consisting of: brombutyric acid chloranil, chloranil methyl, cyproconazole, benzylpyrasulfuron, cyprosulfuron and its salts and esters, dalapon, dazomethanil, diazepam, diazepam-methyl sulfonate, thiamethoxam, DSMA, cyproconazole, cyprothiocarb and its salts, ethoprop, chloranil, chloranil-isopropyl ester, chloranil-methyl ester, chloranil-M-isopropyl ester, chloranil-M-methyl ester Ester, chlorpyrifos, chlorpyrifos-butyl, furafil, cypermethrin, chlorpyrifos ammonium, indole, maleic hydrazide, fluazifop, metamifop, isoxathiapiprolin, methyl azide, methyl bromide, methyl-chlorpyrifos, methyl iodide, MSMA, oleic acid, oxazithromycin, nonanoic acid, chlorpyrifos, chlorpyrifos-butyl, fluazifop, chlorpyrifos, and 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (CAS 499223-49-3) and its salts and esters, and 6-chloro-4-(2,7-dimethyl-1-naphthyl)-5-hydroxy-2-methyl-pyridazin-3-one (CAS 2414510-21-5) (HST inhibitor; FMC).

[0287] More preferably, the herbicide compound of the herbicidal formulation or aqueous spray liquid according to the invention comprises a herbicide compound of group (a), in particular selected from the group consisting of glufosinate, glufosinate salts and combinations thereof.

[0288] In particular, the herbicide compound of group (a) of the herbicidal formulation or aqueous spray liquid according to the invention comprises a glufosinate salt selected from the group consisting of sodium, potassium and ammonium glufosinate (NH4 + )Salt.

[0289] In particular, the herbicide compound of group (a) of the herbicidal formulations or aqueous spray liquids according to the invention is a salt of L-glufosinate, in particular selected from the group consisting of sodium, potassium and ammonium L-glufosinate (NH4 + )Salt.

[0290] According to a preferred embodiment of the herbicidal formulation of the present invention or the aqueous spray liquid of the present invention, the herbicidal formulation or the aqueous spray liquid contains at least one additional herbicide. Examples of suitable additional herbicides are as described above. The concentration of the additional herbicide, the weight ratio of the alkyl ether sulfate of formula (I) to the additional herbicide, and the weight ratio of the herbicidal compound to the additional herbicide are also as described above. In this group of embodiments, the weight ratio refers to the total weight of the herbicidal formulation or the total weight of the aqueous spray liquid.

[0291] (b) Particularly preferably, the herbicide compounds of the herbicidal formulations or aqueous spray liquors according to the invention comprise at least one further herbicide compound which is selected from the group consisting of the herbicidal compounds of groups (b) to (o): the group of enolpyruvylshikimate 3-phosphate synthase inhibitors (EPSP inhibitors);

[0292] (c) herbicidal compounds from the group of acetolactate synthase inhibitors (ALS inhibitors);

[0293] (d) herbicidal compounds from the group of protoporphyrinogen-IX oxidase inhibitors;

[0294] (e) herbicidal compounds from the group of auxin herbicides and auxin transport inhibitors;

[0295] (f) herbicide compounds from the group of photosynthesis inhibitors;

[0296] (g) herbicidal compounds from the group of lipid biosynthesis inhibitors (acetyl-CoA carboxylase inhibitors, ACCase inhibitors);

[0297] (h) lipid biosynthesis inhibitors other than ACCase inhibitors;

[0298] (i) bleaching agent herbicides;

[0299] (j) 7,8-dihydropteroate synthase inhibitors (DHP inhibitors);

[0300] (k) mitotic inhibitors;

[0301] (l) Very long chain fatty acid synthesis inhibitors (VLCFA inhibitors);

[0302] (m) cellulose biosynthesis inhibitors;

[0303] (n) Decoupler herbicides;

[0304] (o) other herbicides selected from the group consisting of: brombutyric acid chloranil, chloranil methyl, cyproconazole, benzylpyrasulfuron, cyprosulfuron and its salts and esters, dalapon, dazomethanil, diazepam, diazepam-methyl sulfonate, thiamethoxam, DSMA, cyproconazole, cyprothiocarb and its salts, ethoprop, chloranil, chloranil-isopropyl ester, chloranil-methyl ester, chloranil-M-isopropyl ester, chloranil-M-methyl ester Ester, chlorpyrifos, chlorpyrifos-butyl, furafil, cypermethrin, chlorpyrifos ammonium, indole, maleic hydrazide, fluazifop, metamifop, isoxathiapiprolin, methyl azide, methyl bromide, methyl-chlorpyrifos, methyl iodide, MSMA, oleic acid, oxazithromycin, nonanoic acid, chlorpyrifos, chlorpyrifos-butyl, fluazifop, chlorpyrifos, and 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (CAS 499223-49-3) and its salts and esters, and 6-chloro-4-(2,7-dimethyl-1-naphthyl)-5-hydroxy-2-methyl-pyridazin-3-one (CAS 2414510-21-5) (HST inhibitor; FMC).

[0305] The herbicidal formulations or aqueous spray liquors according to the invention can be used for controlling undesirable vegetation both on crop areas and on non-crop areas.

[0306] The herbicidal formulations or aqueous sprays according to the invention control undesirable plant growth on uncultivated surfaces very well, especially at high application rates. In crops such as wheat, rice, corn, soybeans and cotton, they are effective against weeds and harmful grasses without significantly damaging the cultivated plants. This effect occurs primarily at low application rates.

[0307] Herbicidal formulations or aqueous sprays allow very efficient control of undesirable vegetation on non-crop areas and in crops. In non-crop areas, very effective control is achieved with high application rates. Depending on the herbicide active compound, the application of the spray allows effective control of broadleaf weeds and grass weeds in crops such as wheat, rice, corn, soybeans and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low application rates.

[0308] Spraying liquid is applied to undesirable plants mainly by spraying leaves usually.Here, application can be carried out by conventional spraying technology using about 10 to 1000l / ha of spraying liquid amount.The application of spraying liquid can be before, during and / or after the emergence of undesirable plants, preferably during and / or after.When using in plant protection, the amount of glufosinate or its salt (not containing formulation auxiliary) depends on the kind of desired effect is 10g / ha to 2kg / ha, particularly 20g / ha to 1.5kg / ha, especially 25g / ha to 1.0kg / ha, calculated with active herbicide compound.

[0309] Depending on the particular method of application, the herbicidal formulations or aqueous spray liquors according to the invention can also be employed in a further number of cultivated plants for combating undesirable vegetation. For example, the following cultures are contemplated: onion (Allium cepa), pineapple (Ananas comosus), peanut (Arachis hypogaea), asparagus (Asparagus officinalis), beet (Beta vulgaris spec. altissima), beet (Beta vulgaris spec. rapa), rapeseed (Brassicanapus var. napus), rutabaga (Brassica napus var. napobrassica), turnip (Brassica rapa var. silvestris), wild tea tree (Camellia sinensis), safflower (Carthamus tinctorius), pecan (Caryailli Boinensis), lemon (Citrus limon), sweet orange (Citrus sinensis), coffee (Coffea arabica) (Coffea canephora, Coffea liberica), cucumber (Cucumis sativus), bermudagrass (Cynodondactylon), carrot (Daucus carota), African oil palm (Elaeis guineensis), wild strawberry (Fragaria vesca), soybean (Glycine max), upland cotton (Gossypium hirsutum), (tree cotton (Gossypium arboreum), grass cotton (Gossypium herbaceum), grape leaf cotton (Gossypium vitifolium)), sunflower (Helianthus annuus), rubber tree (Hevea brasiliensis), barley (Hordeum vulgare), hops (Humulus lupulus), sweet potato (Ipomoea batatas), walnut (Juglans regia), lentil (Lens culinaris), flax (Linum usitatissimum), tomato (Lycopersicon lycopersicum), crabapple (Malus spec.), cassava (Manihot esculenta), alfalfa (Medicago sativa), banana (Musa spec.), tobacco (Nicotiana tabacum) (N. rustica), olive (Olea europaea), rice (Oryza sativa), cotton bean (Phaseolus lunatus), kidney bean (Phaseolus vulgaris), European spruce (Picea abies), pine (Pinus spec.), pea (Pisum sativum), sweet cherry (Prunus avium), peach (Prunus persica), pear (Pyrus communis), currant (Ribes sylvestre), castor (Ricinus communis), sugarcane (Saccharum officinarum), rye (Secale cereale), potato (Solanum tuberosum), sorghum (Sorghum bicolor) (Sorghum vulgare), cocoa (Theobroma cacao), red clover (Trifolium umpratense), wheat (Tritium aestivum), durum wheat (Tritium durum), broad bean (Vicia faba), grapes (Vitis vinifera), and corn (Zea mays).

[0310] In addition, the herbicidal formulations or aqueous sprays can also be used in cultures that have been bred (including genetically) to tolerate the effects of herbicides. In addition, the herbicidal formulations or aqueous sprays according to the invention can also be used in cultures that have been bred (including genetically) to tolerate insect or fungal attack.

[0311] The term "crop" as used herein also includes (crop) plants that have been modified by mutagenesis or genetic engineering to provide new traits to plants or modify existing traits. Mutagenesis includes random mutagenesis techniques using X-rays or mutagenic chemicals, but there is also targeted mutagenesis techniques to produce mutations at specific loci of plant genomes. Targeted mutagenesis techniques often use oligonucleotides or proteins like CRISPR / Cas, zinc finger nucleases, TALEN or meganucleases to achieve targeted effects. Genetic engineering usually uses recombinant DNA technology to produce modifications in plant genomes, which cannot be easily obtained by hybridization, mutagenesis or natural recombination under natural conditions. Typically, one or more genes are integrated into the genome of the plant to increase traits or improve traits. These integrated genes are also referred to as transgenics in the art, and plants containing such transgenics are referred to as transgenic plants. The plant transformation process usually produces several transformation events, which are different on the genomic loci where transgenics have been integrated. Plants containing specific transgenics on specific genomic loci are usually described as containing specific "events", which are referred to by specific event names. Traits that have been introduced into plants or have been modified include, inter alia, herbicide tolerance, insect resistance, increased yield and tolerance to abiotic conditions like drought.

[0312] Herbicide tolerance has been generated by the use of mutagenesis as well as by genetic engineering. Plants that have been rendered tolerant to acetolactate synthase (ALS) inhibitor herbicides by conventional mutagenesis and breeding methods include those that may be named Commercially available plant varieties. However, most herbicide tolerance traits have been generated through the use of transgenics.

[0313] Herbicide tolerance has been developed to glyphosate, glufosinate, 2,4-D, dicamba, oxynil herbicides like bromoxynil and ioxynil, sulfonylurea herbicides, ALS inhibitor herbicides, and 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors like isoxathiapiprolin and mesotrione.

[0314] Transgenics that have been used to provide herbicide tolerance traits include: for glyphosate tolerance: cp4 epsps, epsps grg23ace5, mepsps, 2mepsps, gat4601, gat4621 and goxv247, for glufosinate tolerance: pat and bar, for 2,4-D tolerance: aad-1 and aad-12, for dicamba tolerance: dmo, for benzonitrile herbicide tolerance: bxn, for sulfonylurea herbicide tolerance: zm-hra, csr1-2, gm-hra, S4-HrA, for ALS inhibitor herbicide tolerance: csr1-2, for HPPD inhibitor herbicide tolerance: hppdPF, W336 and avhppd-03.

[0315] Transgenic maize events comprising herbicide tolerance genes are, for example, but not exclusively, DAS40278, MON801, MON802, MON809, MON810, MON832, MON87411, MON87419, MON87427, MON88017, MON89034, NK603, GA21, MZHGOJG, HCEM485, 676, 678, 680, 33121, 4114, 59122, 98140, Bt10, Bt176, CBH-351, DBT418, DLL25, MS3, MS6, MZIR098, T25, TC1507 and TC6275.

[0316] Transgenic soybean events comprising herbicide tolerance genes are, for example, but not exclusively, GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21, A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS-81419-2, GU262, W62, W98, FG72 and CV127.

[0317] Transgenic cotton events comprising a herbicide tolerance gene are, for example, but not exclusively, 19-51a, 31707, 42317, 81910, 281-24-236, 3006-210-23, BXN10211, BXN10215, BXN10222, BXN10224, MON1445, MON1698, MON88701, MON88913, GHB119, GHB614, LLCotton25, T303-3, and T304-40.

[0318] Transgenic canola events comprising a herbicide tolerance gene are, for example, but not exclusively, MON88302, HCR-1, HCN10, HCN28, HCN92, MS1, MS8, PHY14, PHY23, PHY35, PHY36, RF1, RF2, and RF3.

[0319] Insect resistance is mainly produced by transferring bacterial genes of insecticidal proteins into plants. The most commonly used transgenics are toxin genes of Bacillus species (Bacillus spec.) and their synthetic variants, like cry1A, cry1Ab, cry1Ab-Ac, cry1Ac, cry1A.105, cry1F, cry1Fa2, cry2Ab2, cry2Ae, mcry3A, ecry3.1Ab, cry3Bb1, cry34Ab1, cry35Ab1, cry9C, vip3A (a), vip3Aa20. However, plant-derived genes are also transferred into other plants. In particular, genes encoding protease inhibitors, such as CpTI and pinII. Other methods use transgenics to produce double-stranded RNA in plants to target and lower insect genes. The example of this transgenic is dvsnf7.

[0320] Transgenic maize events comprising a gene for an insecticidal protein or double-stranded RNA are, for example, but not exclusively, Bt10, Bt11, Bt176, MON801, MON802, MON809, MON810, MON863, MON87411, MON88017, MON89034, 33121, 4114, 5307, 59122, TC1507, TC6275, CBH-351, MIR162, DBT418 and MZIR098.

[0321] Transgenic soybean events comprising a gene for an insecticidal protein are for example, but not exclusively, MON87701, MON87751 and DAS-81419.

[0322] Transgenic cotton events comprising a gene for an insecticidal protein are, for example, but not exclusively, SGK321, MON531, MON757, MON1076, MON15985, 31707, 31803, 31807, 31808, 42317, BNLA-601, Event1, COT67B, COT102, T303-3, T304-40, GFM Cry1A, GK12, MLS 9124, 281-24-236, 3006-210-23, GHB119 and SGK321.

[0323] Increased yield is achieved by increasing ear biomass using the transgene athb17 present in maize event MON87403, or by enhancing photosynthesis using the transgene bbx32 present in soybean event MON87712.

[0324] Crops with improved oil content have been produced using the following transgenes:

[0325] gm-fad2-1, Pj.D6D, Nc.Fad3, fad2-1A, and fatb1-A. Soybean events containing at least one of these genes are: 260-05, MON87705, and MON87769.

[0326] Tolerance to abiotic conditions, in particular drought tolerance, has been demonstrated through the use of the transgene cspB contained in maize event MON87460 and through the use of the transgene cspB contained in soybean event The included transgenic Hahb-4 was produced.

[0327] Traits are usually combined by combining genes in a transformation event or by combining different events during the breeding process. Preferred combinations of traits are herbicide tolerance to different groups of herbicides, insect tolerance to different species of insects, in particular tolerance to Lepidoptera and Coleoptera, herbicide tolerance in combination with one or several types of insect resistance, herbicide tolerance with increased yield and herbicide tolerance with tolerance to abiotic conditions.

[0328] Plants containing single or stacked traits and genes and events providing these traits are well known in the art. For example, detailed information on mutagenic or integrated genes and corresponding events can be obtained from the International Service for the Application of Agri-biotech Applications (ISAAA) (http: / / www.isaaa.org / gmapprovaldatabase) and the Center for Environmental Risk Assessment (CERA) (http: / / www.isaaa.org / gmapprovaldatabase). http: / / cera-gmc.org / GMCropDatabase )'s website and patent applications like EP3028573 and WO2017 / 011288.

[0329] The use of the spray according to the invention on crops may result in specific effects on crops containing a gene or event. These effects may involve changes in growth behavior or altered resistance to biotic or abiotic stress factors. Such effects may particularly include increased yield, increased resistance or tolerance to insects, nematodes, fungi, bacteria, mycoplasmas, viruses or viroid pathogens and early vigour, early or delayed maturity, cold or heat tolerance and altered amino acid or fatty acid profiles or contents.

[0330] Furthermore, plants containing modified amounts of components or novel components by the use of recombinant DNA techniques, in particular to improve raw material production, such as potatoes producing increased amounts of amylopectin (e.g. Potatoes, BASF SE, Germany).

[0331] In addition, it has been found that the combination of alkyl ether sulfates of formula (I) with herbicides can also be suitable for defoliation and / or dehydration of plant parts of crop plants such as cotton, potatoes, rape, sunflower, soybean or broad bean, in particular cotton. In this regard, herbicidal compositions for dehydration and / or defoliation of plants, methods for preparing these compositions and methods for dehydration and / or defoliation of plants using the herbicidal compositions according to the invention have been found.

[0332] As dehydrating agents, the herbicidal compositions according to the invention are particularly suitable for dehydrating the above-ground parts of crop plants such as potatoes, rape, sunflowers and soybeans and also cereals. This enables fully mechanized harvesting of these important crop plants.

[0333] Also of economic interest is the promotion of the harvest of pome, drupe and nuts of citrus fruits, olives and other species and varieties, which is made possible by concentrated cracking or reduced sticking to the tree over a certain period of time. The same mechanism, namely the promotion of the development of abscission tissue between the fruit part or the leaf part and the branch part of the plant, is also necessary for the controlled defoliation of useful plants, in particular cotton.

[0334] Furthermore, the shortening of the time interval between maturity of individual cotton plants results in improved fiber quality after harvest.

[0335] The combination of an alkyl ether sulfate of formula (I) and a herbicide can be applied in or on permanent farmland, or on permanent crops. Permanent crops are crops produced from plants that continue for multiple seasons, rather than crops that are replanted after each harvest. Permanent crops grow on permanent farmland in the form of agricultural land, which includes grassland and shrubland, for example, for growing grapevines or coffee; orchards, for growing fruit or olives; and forest plantations, for example, for growing nuts or rubber. However, it does not include forestry intended for wood or timber.

[0336] In the context of the present invention, preferred permanent croplands are plantations, grasslands and scrublands. Preferably, in the context of the present invention, permanent crops are plantation crops, and are preferably selected from the group consisting of fruit crops and orchard crops (preferably fruit trees, citrus trees, mango trees, olive trees, grapevines, coffee, cocoa, tea and berries (such as strawberries, raspberries, blueberries and currants)), Musaceae species crops (e.g. banana or plantain crops), nut trees (preferably almond trees, walnut trees, pistachio trees, pecan trees, hazelnut trees), oil palm trees, rubber trees, sugar cane and cotton.

[0337] More preferably, the permanent crops are fruit trees (preferably pome and stone fruit trees; preferred fruit trees are apple, pear, almond, plum, cherry, peach), olive trees, grapevines, coffee, tea), Musaceae crops (preferably banana crop or plantain crop), nut trees (preferably almond, walnut, pistachio, pecan, hazelnut), oil palm, rubber trees and citrus crops (preferably lemon, orange or grapefruit crops). Even more preferably, the permanent crops are selected from the group consisting of apple trees, pear trees, almond, plum, cherry, peach, olive trees, grapevines, coffee, tea, banana crop, nut trees (preferably almond, walnut, pistachio), oil palm, rubber trees and citrus crops (preferably lemon, orange or grapefruit crops). Particularly preferably, the permanent crop is selected from the group consisting of apple trees, pear trees, almond trees, plum trees, cherry trees, peach trees, olive trees, grapevines, coffee, tea, banana crops, almond trees, walnut trees, oil palm trees, rubber trees, lemon crops, orange crops and grapefruit crops.

[0338] The combination of alkyl ether sulfates of formula (I) with herbicides can also be applied to row crops and also to specialty crops.

[0339] Row crops can be planted in wide enough rows to allow them to be cultivated or otherwise grown by agricultural machinery, machinery customized for seasonal activities of row crops. The particularity of row crops is that they are planted and cultivated based on seasons or years. Therefore, this type of crop produces products and profits relatively quickly and predictably. Row crops are crops produced from plants that last for many seasons, rather than crops that are planted again after each harvest. Examples of row crops include soybeans, corn, canola, cotton, cereals or rice, as well as sunflowers, potatoes, dry beans, peas, flax, safflower, buckwheat and sugar beets.

[0340] Specialty crops are understood to be fruits, vegetables or other specialty or plantation permanent crops, such as trees, nuts, vines, (dried) fruits, ornamental plants, oil palm, bananas, rubber, etc., horticultural and nursery crops, including cultivated flowers, may also fall within the definition of specialty crops. Vegetable crops include, for example, aubergine, beans, bell peppers, cabbage, peppers, cucumbers, eggplants, lettuce, melons, onions, potatoes, sweet potatoes, spinach and tomatoes. Plants considered to be specialty crops are usually cultivated intensively. For weed control in vegetable crops, it may be desirable to protect the crop from contact with a spray solution containing the herbicidal mixture according to the invention.

[0341] Typically, the crop that can be treated with the combination of the alkyl ether sulfate with the formula (I) and the herbicide can be of conventional origin or can be a herbicide tolerant crop, preferably at least a crop tolerant to one of glufosinate, glyphosate and / or dicamba. The combination of the alkyl ether sulfate with the formula (I) and the herbicide also shows a high weeding effect for selected crop plants such as barley and soybean. This effect can be used to control crop plants in the crop rotation method of the previously grown crop culture. Typically, the residual crop plants from the previous rotation cycle are retained after harvest, and continue to grow in the crop variety subsequently grown. This reduces yield because the crop plants of two different crop rotation cycles compete in the same growth place. Therefore, the combination of the alkyl ether sulfate with the formula (I) and the herbicide can be applied to control the residual crop plants from the previous crop rotation cycle, thereby allowing the uniform coverage of subsequent crop plants.

[0342] In a preferred embodiment, the combination of an alkyl ether sulfate of formula (I) and a herbicide is applied once, twice or three times per calendar year, i.e., one application, two applications or three applications are carried out per calendar year. In a preferred embodiment, the herbicidal composition is applied twice per calendar year, i.e., two applications are carried out per calendar year. In an alternative preferred embodiment, the combination of an alkyl ether sulfate of formula (I) and a herbicide is applied once per calendar year, i.e., one application is carried out per calendar year. In a preferred embodiment, the herbicidal composition is applied once in about 12 months, i.e., one application is carried out per calendar year. In an alternative preferred embodiment, the combination of an alkyl ether sulfate of formula (I) and a herbicide is applied one to ten times per calendar year, i.e., up to ten applications are carried out per calendar year. This alternative preferred method is particularly useful in permanent crops, especially those grown under tropical conditions; in this case, weeds grow vigorously at any time of the year, and herbicide applications will be repeated as soon as the previous treatment loses its effectiveness and the weeds begin to grow again.

[0343] The present invention comprises the use and application method of the combination of alkyl ether sulfates of formula (I) and herbicides for controlling unwanted vegetation in crops in a pest control program, wherein the crops are genetically engineered or produced by breeding to be tolerant to one or more herbicides and / or to pathogens such as phytopathogenic fungi and / or to insect attack; preferably tolerant to glufosinate-ammonium.

[0344] Preference is given to crops that are tolerant to glufosinate, wherein the glufosinate tolerant crop plants are preferably selected from the group consisting of rice, canola, soybean, corn and cotton plants.

[0345] The transgenic maize event comprising the glufosinate tolerance gene is, for example, but not exclusively, 5307x MIR604x Bt11 x TC1507x GA21 x MIR162 (Event Code: Gene: pat, for example, as Duracade TM 5222 commercially available), 59122 (event code: DAS-59122-7, gene: pat, e.g., as Herculex TM RW commercially available), 5307x MIR604 x Bt11 x TC1507 x GA21 (Event Code: Gene: pat, for example, as Duracade TM 5122 commercially available), 59122x NK603 (event code: Gene: pat, for example, as Herculex TM RW Roundup Ready TM 2 commercially available), Bt10 (gene: pat, for example, commercially available as Bt10), Bt11 (X4334CBR, X4734CBR) (event code: Gene: pat, for example, as Agrisure TM CB / LL commercially available), BT11 x 59122x MIR604 x TC1507 x GA21 (Event Code: SYN- Gene: pat, for example, as 3122 commercially available), Bt11 x GA21 (Event code: Gene: pat, for example, as Agrisure TM GT / CB / LL commercially available), Bt11 x MIR162 (Event Code: Gene: pat, for example, as Viptera TM 2100 commercially available), Bt11x MIR162 x GA21 (Event Code: Gene: pat, for example, as Viptera TM 3110 commercially available), BT11x MIR162x MIR604 (Event Code: Gene: pat, for example, as VipteraTM 3100 commercially available), Bt11 x MIR162 x MIR604 x GA21 (Event Code: Gene: pat, for example, as Viptera TM 3111, Viptera TM 4 commercially available), Bt11 x MIR162 x TC1507 x GA21 (Event Code: Gene: pat, for example, as Agrisure TM Viptera 3220 commercially available), Bt11x MIR604 (event code: Gene: pat, for example, as Agrisure TM CB / LL / RW commercially available), BT11x MIR604 x GA21 (Event Code: Gene: pat, for example, as Agrisure TM 3000GT commercially available), Bt176 (176) (event code: SYN-EV176-9, gene: bar, for example, as NaturGard KnockOut TM , Maximizer TM Commercially available), CBH-351 (Event code: Gene: bar, for example, as Starlink TM Zea mays commercially available), DBT418 (event code: DKB-89614-9, gene: bar, e.g., as Bt Xtra TM corn commercially available), MON89034 x TC1507 x MON88017 x 59122 (Event Code: Gene: pat, for example, as SmartStax TM Commercially available), MON89034x TC1507 x NK603 (Event code: Gene: pat, for example, as Power Core TM Commercially available), NK603 x T25 (Event code: Gene: pat, for example, as RoundupReady TM Liberty Link TMCorn was purchased from a commercial source), T14 (event code: Gene:pat, for example, as Liberty Link TM Corn was purchased from a commercial source), T25 (event code: Gene:pat, for example, as Liberty Link TM corn commercially available), T25 x MON810 (event code: Gene:pat, for example, as Liberty Link TM Yieldgard TM Corn was purchased commercially), TC1507 (event code: Gene: pat, for example, as Herculex TM I. Herculex TM CB commercially available), TC1507 x 59122xMON810 x MIR604 x NK603 (Event Code: Gene: pat, for example, as Optimum TM Intrasect Xtreme commercially available), TC1507 x 59122 (Event Code: Gene: pat, for example, as Herculex XTRA TM Commercially available), TC1507 x59122x MON810 x NK603 (Event code: Gene: pat, for example, as Optimum TM Intrasect XTRA commercially available), TC1507 x 59122x NK603 (Event Code: Gene: pat, for example, as Herculex XTRA TM RR commercially available), TC1507 x MIR604 x NK603 (Event Code: Gene: pat, for example, as Optimum TM TRIsect commercially available), TC1507x MON810 x NK603 (Event Code: Gene: pat, for example, as Optimum TM Intrasect commercially available), TC1507 x NK603 (Event Code: Gene: pat, for example, as Herculex TMI RR commercially available), 3272x Bt11 (event code: Gene: pat), 3272x Bt11x GA21 (Event code: Gene: pat), 3272xBt11x MIR604 (Event code: Gene: pat), 3272x BT11xMIR604 x GA21 (Event code: Gene: pat), 33121 (event code: 3, gene: pat), 4114 (event code: Gene: pat), 59122xGA21 (event code: Gene: pat), 59122x MIR604 (event code: Gene: pat), 5307x MIR604 x Bt11 x TC1507 x GA21 x MIR162 (Event Code: , Gene: pat), 59122x MIR604 x GA21 (Event Code: Gene: pat), 59122x MIR604x TC1507 (Event Code: Gene: pat), 59122x MIR604x TC1507 x GA21 (Event Code: , Gene: pat), (Event Code: Gene: pat), 59122x MON810 (event code: Gene: pat), 59122x MON810xNK603 (event code: Gene: pat), 59122x TC1507xGA21 (Event code: Gene: pat), 676 (event code: Gene: pat), 678 (event code: Gene: pat), 680(Event code: Gene: pat), 98140x 59122(Event code: Gene: pat), 98140x TC1507 (event code: Gene: pat), 98140x TC1507x 59122 (Event code: Gene: pat), 59122x MON88017 (event code: Gene: pat), Bt11 x 59122 (Event code: Gene: pat), Bt11 x 59122x GA21 (Event code: Gene: pat), Bt11x 59122x MIR604 (Event code: Gene: pat), Bt11x 59122x MIR604 x GA21 (Event code: Gene: pat), Bt11x 59122x MIR604xTC1507 (Event code: Bt11 x 59122x MIR604 x TC1507, Gene: pat), Bt11 x 59122x TC1507 (Event code: Gene: pat), Bt11x 59122x TC1507 xGA21 (Event code: Gene: pat), Bt11xMIR162 x TC1507 (Event code: Gene: pat), Bt11xMIR604 x TC1507 (Event code: Gene: pat), Bt11xTC1507 (event code: Gene: pat), Bt11x TC1507 x GA21 (Event code: Gene: pat), GA21x T25 (event code: gene: pat), MIR162 x TC1507 (event code: Gene: pat), MIR162x TC1507 x GA21 (Event code: Gene: pat), MIR604x TC1507 (event code: Gene: pat), (Event code: Gene: pat), MON89034x 59122 (event code: Gene: pat), MON89034 x 59122xMON88017 (Event Code: , Gene: pat), MON89034 x TC1507 (Event Code: Gene: pat), (Event code: Gene: pat), MIR604x TC1507 (event code: 1. Gene: pat), (Event code: Gene: pat), MON89034x 59122 (event code: Gene: pat), MON89034x 59122x MON88017 (Event Code: , Gene: pat), MON89034 x TC1507 (Event Code: Gene: pat), (Event code: Gene: pat), DLL25(B16)(Event code: gene: bar), MIR604 x TC1507 (event code: Gene: pat), (Event code: Gene: pat), MON89034x59122 (event code: Gene: pat), MON89034x 59122x MON88017 (Event Code: Gene: pat), MON89034x TC1507 (Event code: Gene: pat), MON89034x TC1507 x 59122 (Event Code: Gene: pat), MON89034x TC1507 x MON88017 (Event Code: Gene: pat), MON89034x TC1507 x MON88017x59122x DAS40278 (Event Code: Gene: pat), MON89034xTC1507 x MON88017 x DAS40278 (Event Code: Gene: pat), MON89034x TC1507 x NK603 xDAS40278 (Event Code: Gene: pat), NK603x MON810x 4114x MIR 604 (Event Code: MON-00603-6x MON-00810-6x DP004114-3xSYN-IR604-4, Gene: pat), TC1507 x MON810 x MIR604 x NK603 (Event Code: Gene: pat), TC1507x 59122xMON810 (Event code: Gene: pat), TC1507x 59122xMON88017 (Event code: Gene: pat), TC1507 x GA21 (Event code: Gene: pat), TC1507 x MON810 (Event code: Gene: pat), TC1507x MON810 x MIR162 x NK603 (Event Code: Gene: pat), 3272x Bt11x MIR604xTC1507 x 5307x GA21 (Event Code: Gene: pat), TC1507x MIR162 x NK603 (Event Code: Gene: pat), TC1507x MON810 x MIR162 (Event Code: Gene: pat), MON87419 (Event code: MON87419-8, Gene: pat), TC1507x MON88017 (Event code: Gene: pat), TC6275 (event code: Gene: bar), MZHG0JG (event code: Gene: pat), MZIR098 (event code: Gene: pat), Bt11 xMIR162 x MON89034 (Event Code: Gene: pat) and (Event code: Gene: pat), 59122x DAS40278 (Event code: Gene: pat), 59122x MON810 x MIR604 (Event Code: Gene: pat), 59122x MON810x NK603 x MIR604 (Event Code: Gene: pat), 59122x MON88017 xDAS40278 (Event code: Gene: pat), 59122x NK603 xMIR604 (Event code: Gene: pat), Bt11 x5307 (event code: Gene: pat), Bt11x 5307x GA21 (Event code: Gene: pat), Bt11x MIR162 x 5307 (Event code: Gene: pat), Bt11x MIR162 x 5307x GA21 (Event Code: Gene: pat), BT11x MIR162 x MIR604 x 5307 (Event code: Gene: pat), Bt11x MIR162 x MIR604 x 5307x GA21 (Event Code: Gene: pat), Bt11x MIR162x MIR604 x MON89034 x 5307x GA21 (Event Code: Gene: pat), BT11x MIR162 x MIR604 x TC1507 (Event Code: Gene: pat), BT11x MIR162 xMIR604 xTC1507 x 5307 (Event Code: Gene: pat), Bt11 x MIR162x MIR604 x TC1507 x GA21 (Event Code: Gene: pat), Bt11x MIR162 x TC1507 x 5307 (Event Code: Gene: pat), BT11x MIR162 x MIR604 x TC1507 x 5307 (Event Code: Gene: pat), Bt11xMIR162 x MIR604 x TC1507 x GA21 (Event Code: Gene: pat), Bt11x MIR162x TC1507 x 5307 (Event Code: Gene: pat), Bt11x MIR162 x TC1507 x 5307x GA21 (Event Code: Gene: pat), Bt11x MIR604 x5307 (event code: Gene: pat), Bt11x MIR604 x 5307xGA21 (Event code: Gene: pat), Bt11xMIR604 x TC1507x 5307 (Event code: Gene: pat), Bt11x MIR604x TC1507 x GA21 (Event Code: Gene: pat), Bt11 x MON89034 (or )(Event code: Gene: pat), Bt11x MON89034 x GA21 (Event code: Gene: pat), (Event code: Gene: pat), Bt11x TC1507x 5307 (Event code: Gene: pat), Bt11x TC1507 x 5307xGA21 (Event code: Gene: pat), MIR162x MIR604 xTC1507 x 5307 (Event Code: Gene: pat), MIR162 x MIR604 x TC1507 x 5307 x GA21 (Event Code: Gene: pat), MIR162xMIR604 x TC1507 x GA21 (Event Code: Gene: pat), MIR162x TC1507 x 5307 (Event code: Gene: pat), MIR162x TC1507 x 5307x GA21 (Event code: Gene: pat), MIR604x TC1507 x 5307 (Event code: Gene: pat), MIR162x TC1507 x 5307 (Event code: Gene: pat), MIR162x TC1507 x 5307x GA21 (Event code: Gene: pat), MIR604x TC1507x 5307 (event code: Gene: pat), MIR604x TC1507 x5307xGA21 (Event code: Gene: pat), MIR604xTC1507 x GA21 (Event code: Gene: pat), MON87427x59122 (Event code: MON-87427-7x DAS-59122-7, Gene: pat), MON87427 x MON89034 x 59122 (Event code: Gene: pat), MON87427x MON89034 xMON88017 x 59122 (Event Code: Gene: pat), MON87427x MON89034 x TC1507 (Event Code: Gene: pat), MON87427x MON89034 x TC1507 x 59122 (Event Code: Gene: pat), MON87427xMON89034 xTC1507 x MON87411 x 59122 (Event Code: Gene: pat), MON87427x MON89034 x TC1507 x MON87411 x 59122xDAS40278 (Event Code: Gene: pat), MON87427 x MON89034 x TC1507 x MON88017 (Event Code: Gene: pat), MON87427x TC1507 (Event code: Gene: pat), MON87427x TC1507 x 59122 (Event Code: Gene: pat), MON87427 x TC1507 x MON88017 (Event Code: Gene: pat), MON87427x TC1507 x MON88017 x59122 (Event Code: Gene: pat), MON89034x 59122x DAS40278 (Event code: Gene: pat), MON89034x 59122x MON88017 x DAS40278 (Event Code: Gene: pat), MON89034x TC1507 x 59122xDAS40278 (Event Code: Gene: pat), MON89034xTC1507 x DAS40278 (Event Code: Gene: pat), MON89034x TC1507 x NK603 x MIR162 (Event Code: Gene: pat), TC1507 x 5307 (event code: Gene: pat), TC1507 x 5307x GA21 (Event Code: Gene: pat), TC1507x 59122x DAS40278 (Event code: Gene: pat), TC1507x 59122x MON810 x MIR604 (Event Code: Gene: pat), TC1507x59122x MON88017 x DAS40278 (Event Code: Gene: pat), TC1507 x 59122x NK603 xMIR604 (Event Code: , Gene: pat) TC1507x DAS40278 (Event Code: Gene: pat), TC1507 x MON810 xMIR604 (Event Code: Gene: pat), TC1507 x MON810 x NK603 x MIR604 (Event Code: Gene: pat), TC1507x MON88017 x DAS40278 (Event Code: gene: pat) and TC1507 x NK603 x DAS40278 (event code: Gene: pat).

[0346] The transgenic soybean event containing the glufosinate tolerance gene is, for example, but not exclusively, A2704-12 (event code: Gene:pat, for example, as Liberty Link TM Soybeans were purchased commercially), A2704-21 (Event Code: Gene:pat, for example, as Liberty Link TM Soybeans were purchased commercially), A5547-127 (Event Code: Gene:pat, for example, as Liberty Link TM Soybeans were purchased commercially), A5547-35 (Event Code: Gene:pat, for example, as Liberty Link TM Soybeans were purchased commercially), GU262 (Event Code: Gene:pat, for example, as Liberty Link TM Soybeans purchased from commercial sources), W62 (Event code: Gene:pat, for example, as Liberty Link TM Soybeans purchased from commercial sources), W98 (Event Code: Gene:pat, for example, as Liberty Link TM soybean commercially available), DAS68416-4 (event code: DAS-68416-4, gene: pat, for example, as Enlist TM soybeans were purchased commercially), DAS44406-6 (Event Code: Gene: pat), DAS68416-4x MON89788 (Event code: DAS-68416-4x MON-89788-1, Gene: pat), (Event code: Gene: pat), DAS81419x DAS44406-6 (Event code: gene: pat) and FG72x A5547-127 (event code: Gene: pat).

[0347] The transgenic cotton event comprising the glufosinate tolerance gene is, for example, but not exclusively, 3006-210-23x281-24-236xMON1445 (event code: Gene: bar, for example, as WideStrike TM Roundup Ready TM Cotton purchased from commercial sources), 3006-210-23x 281-24-236x MON88913 (Event Code: Gene: bar, for example, as Widestrike TM Roundup Ready Flex TM Cotton purchased from commercial sources), 3006-210-23x 281-24-236xMON88913 x COT102 (Event Code: Gene: pat, for example, as Widestrike TM x Roundup Ready Flex TM x VIPCOT TM Cotton commercially available), GHB614 xLLCotton25 (Event Code: Gene: bar, for example, as GlyTol TM LibertyLink TM Commercially available), GHB614 x T304-40 x GHB119 (Event Code: Gene: bar, for example, as Glytol TM x Twinlink TM Commercially available), LLCotton25 (Event code: Gene: bar, for example, as Commercially available), GHB614x T304-40x GHB119 x COT102 (Event Code: Gene: bar, for example, as Glytol TM xTwinlink TM x VIPCOT TM Cotton purchased from commercial sources), LLCotton25 x MON15985 (Event Code: Gene: bar, for example, as Fibermax TM Liberty Link TM Bollgard II TM Commercially available), T304-40 x GHB119 (Event Code: Gene: bar, for example, as a TwinLink TM Cotton commercially available), GHB614x T304-40x GHB119x COT102 (Event Code: Gene: bar, for example, as Glytol TM xTwinlink TM x VIPCOT TM Cotton purchased from commercial sources), GHB119 (event code: Gene: bar), GHB614x LLCotton25 x MON15985 (Event Code: Gene: bar), (Event code: MON88701, gene: bar), T303-3 (Event code: Gene: bar), T304-40 (Event code: Gene: bar), (Event code: gene: bar), 81910 (event code: DAS-81910-7, gene: pat), MON8870 (event code: Gene: bar), MON88701x MON88913 (Event Code: Gene: bar), MON88701xMON88913 x MON15985 (Event Code: Gene: bar), 281-24-236x 3006-210-23x COT102x 81910(Event Code: Gene: pat), COT102xMON15985 xMON88913 x MON88701 (Event Code: Gene: bar) and 3006-210-23x 281-24-236x MON88913x COT102 x 81910 (Event Code: Gene: pat).

[0348] A transgenic canola event comprising a glufosinate tolerance gene is, for example, but not exclusively, HCN10 (Topas 19 / 2) (Event Code: , Gene: bar, for example, as Liberty Link TM Independence TM Commercially available), HCN28 (T45) (Event code: Gene: pat, for example, as InVigor TM Canola (commercially available), HCN92 (Topas 19 / 2 (event code: Gene: bar, for example, as a LibertyLink TM Innovator TM Commercially available), MS1 (B91-4) (Event code: Gene: bar, for example, as InVigor TM Canola (commercially available), MS1x RF1 (PGS1) (event code: Gene: bar, for example, as InVigor TMCanola (commercially available), MS1 x RF2 (PGS2) (Event Code: Gene: bar, for example, as InVigor TM Canola oilseed was purchased commercially), MS1 xRF3 (event code: Gene: bar, for example, as InVigor TM Canola rapeseed commercially available), MS8 (event code: Gene: bar, for example, as InVigor TM Canola (commercially available), MS8 x RF3 (Event Code: Gene: bar, for example, as InVigor TM Canola (commercially available), RF1 (B93-101) (event code: Gene: bar, for example, as InVigor TM Canola (commercially available), RF2 (B94-2) (Event Code: Gene: bar, for example, as InVigor TM Canola rape was purchased commercially), RF3 (event code: Gene: bar, for example, as InVigor TM Canola (commercially available), MS1 x MON88302 (Event Code: Gene: bar, for example, as InVigor TM x TruFlex TM Roundup Ready TM Canola (commercially available), MS8 x MON88302 (Event Code: Gene: bar, for example, as InVigor TM x TruFlex TM Roundup Ready TM Canola (commercially available), RF1 x MON88302 (Event Code: Gene: bar, for example, as InVigor TM x TruFlex TM Roundup Ready TM Canola (commercially available), RF2 x MON88302 (Event Code: Gene: bar, for example, as InVigor TM x TruFlex TM RoundupReady TMCanola (commercially available), HCN28 x MON88302 (Event Code: Gene: pat, for example, as InVigor TM x TruFlex TM Roundup Ready TM Canola rape commercially available), HCN92 xMON88302 (event code: Gene: bar, for example, as a LibertyLink TM Innovator TM x TruFlex TM Roundup Ready TM Canola (commercially available), HCR-1 (gene: pat), MON88302 x MS8 x RF3 (event code: Gene: bar), MON88302x RF3 (Event Code: gene: bar), MS8 x RF3 x GT73 (RT73) (event code: , gene: bar), PHY14 (event code: bar), PHY23 (gene: bar), PHY35 (gene: bar), and PHY36 (gene: bar), and 73496x RF3 (event code: Gene: bar).

[0349] The transgenic rice event comprising the glufosinate tolerance gene is, for example, but not exclusively, LLRICE06 (event code: For example, as a Liberty Link TM Rice commercially available), LLRICE601 (event code: For example, as a Liberty Link TM Rice commercially available) and LLRICE62 (event code: For example, as a Liberty Link TM Rice was purchased from a commercial supplier).

[0350] The application of the herbicidal formulations or aqueous sprays can be carried out in the pre-emergence or post-emergence method. If the herbicidal formulations are not very compatible with certain cultivated plants, an application technique can be used in which the herbicidal formulations are sprayed using a spray device so that the leaves of sensitive cultivated plants are not affected where possible, while the herbicidal formulations reach the leaves of undesirable plants growing underground or on the exposed soil surface (post-emergence basal application, last field operation).

[0351] The combination of applying herbicides with copolymers CP provides outstanding herbicidal activity against a broad spectrum of economically important harmful monocotyledonous and dicotyledonous harmful plants. Here, post-emergence application is also preferred.

[0352] In particular, mention may be made of the examples of some representatives of the monocotyledonous and dicotyledonous weed flora which can be controlled by the combinations according to the invention, without this enumeration being a restriction to certain species.

[0353] In the present context, reference may be made to the BBCH monograph “Growth stages of mono-and dicotyledonous plants”, 2nd edition, 2001, ed. Uwe Meier, Federal Biological Research Centre for Agriculture and Forestry (Biologische Bundesanstalt für Land und Forstwirtschaft).

[0354] Examples of monocotyledonous harmful plants against which the glufosinate combination is effective are from the following genera: Hordeum spp., Echinochloa spp., Poa spp., Bromus spp., Digitaria spp., Eriochloa spp., Setaria spp., Pennisetum spp., Eleusine spp., Eragrostis spp., Panicum spp., Lolium spp., Brachiaria spp., Leptochloa spp., Avenaspp., Cyperus spp. spp.), Axonopris spp., Sorghum spp., and Melinus spp.

[0355] Preferred examples of monocotyledonous harmful plant species on which the herbicidal composition is effective are selected from the following species: Hordeummurinum, Echinochloa crus-galli, Poa annua, Bromus rubens L., Bromus rigidus, Bromus secalinus L., Digitaria sanguinalis, Digitaria insularis, Eriochloagracilis, Setaria faberi, Setaria viridis, Pennisetum glaucum, Eleusine indica, Eragrostis pectinacea, Panicum miliaceum, Lolium multiflorum, Brachiaria platyphylla, Leptochloa fusca, Avena fatua, Cyperus compressus, Cyperus esculentes, Axonopris offinis, Sorghum halapense, and Melinus repens.

[0356] In a preferred embodiment, the herbicidal composition is used to control monocotyledonous harmful plant species, more preferably monocotyledonous plants of the genera Echinochloa species, Digitaria species, Setaria species, Eleutherodactyla species and Brachiaria species.

[0357] Examples of dicotyledonous harmful plants against which the herbicidal compositions are effective are from the following genera: Amaranthus spp., Erigeron spp., Conyza spp., Polygonum spp., Medicago spp., Mollugo spp., Cyclospermum spp., Stellaria spp., Gnaphalium spp., Taraxacum spp., Oenothera spp., Amsinckia spp., Erodium spp., Erigeron spp., Senecio spp.), Lamium spp., Kochia spp., Chenopodium spp., Lactuca spp., Malva spp., Ipomoea spp., Brassica spp., Sinapis spp., Urtica spp., Sida spp., Portulaca spp., Richardia spp., Ambrosia spp., Calandrinia spp., Sisymbrium spp., Sesbania spp., Capsella spp.), Sonchus spp., Euphorbia spp., Helianthus spp., Coronopus spp., Salsola spp., Abutilon spp., Vicia spp., Epilobium spp., Cardamine spp., Picris spp., Trifolium spp., Galinsoga spp., Epimedium spp.), Marchantia spp., Solanum spp., Oxalis spp., Metricaria spp., Plantago spp., Tribulus spp., Cenchrus spp., two Bidens spp., Veronica spp., and Hypochaeris spp.

[0358] Specific examples of dicotyledonous harmful plant species against which the herbicidal composition is effective are selected from the following species: Amaranthus spinosus, Polygonum convolvulus, Medicago polymorpha, Mollugo verticillata, Cyclos permumleptophyllum, Stellaria media, Gnaphalium purpureum, Taraxacum officinale, Oenothera laciniata, Amsinckia intermedia, Erodium cicutarium, Erodium moschatum, Erigeron bonariensis (Conyza bonariensis), Senecio vulgaris, Lamium amplexicaule), Erigeron canadensis, Polygonum aviculare, Kochia scoparia, Chenopodium album, Lactuca serriola, Malva parviflora, Malva neglecta, Ipomoea hederacea, Ipomoea lacunose, Brassica nigra, Sinapis arvensis, Urtica dioica, Amaranthus blitoides, Amaranthus retroflexus, Amaranthus hybridus, Amaranthus lividus, Sida spinosa, Portulaca oleracea), Richardiascabra, Ambrosia artemisiifolia, Calandrinia caulescens, Sisymbrium irio, Sesbania exaltata, Capsellabursa-pastoris), Sonchus oleraceus, Euphorbia maculate, Helianthus annuus, Coronopus didymus, Salsola tragus, Abutilon theophrasti, Vicia ben-ghalensis L., Epilobium paniculatum, Cardamine spp., Picris echioides, Trifolium spp., Galinsoga spp., Epimedium spp., Marchantias spp., Solanum spp., Oxalis spp., Metricaria matriccarioides, Plantago spp.), Tribulus terrestris, Salsola kali, Cenchrus spp., Bidens bipinnata, Veronica spp., and Hypochaeris radicata.

[0359] In a preferred embodiment, the herbicidal composition is used to control dicotyledonous harmful plant species, more preferably dicotyledonous plants of the genera Amaranthus, Erigeron, Amaranthus, Kochia and Abutilon.

[0360] A large number of annual and perennial sedge weeds, including sedge species such as purple nutsedge (Cyperus rotundus L.), yellow nutsedge (Cyperus esculentus L.), hime-kugu (Cyperus brevifolius H.), sedge weeds (Cyperus microiria Steud), rice sedge (Cyperusiria L.), Cyperus difformis, Cyperus difformis L., Cyperus esculentus, Cyperus ferax, Cyperus flavus, Cyperusiria, Cyperus lanceolatus, Cyperus microiria Steud ... odoratus), Cyperus rotundus, Cyperus serotinus Rottb., Eleocharis acicularis, Eleocharis kuroguwai, Fimbristylis dichotoma, Fimbristylismiliacea, Scirpus grossus, Scirpus juncoides, Scirpusjuncoides Roxb, Seaside Three-edged Grass (Scirpus or Bolboschoenus maritimus), Northern Water Hair Flower (Scirpus or Schoenoplectus mucronatus), Scirpus planiculmis Fr. Schmidt, etc.

[0361] If the spray solution is applied post-emergence to the green parts of the plants, growth is also arrested sharply within a very short time after the treatment and the weed plants remain at the growth stage at the time of application or they die completely after a certain time, so that in this way weed competition that is harmful to the crop is eliminated at a very early point in time and in a permanent manner.

[0362] The application of a combination of herbicides and copolymers CP results in a fast onset and long-lasting herbicidal action. In general, the fastness of the herbicide active compounds in the combination according to the invention to rain washout is advantageous. In particular, when using herbicidal compositions, the application rate can be reduced, a wider spectrum of broadleaf weeds and grass weeds can be controlled, the herbicidal action can occur more quickly, the duration of action can be longer, harmful plants can be better controlled, while only one or a few applications are used, and the application period can be extended.

[0363] The above-mentioned properties and advantages are beneficial for weed control practices in order to keep crops free from undesirable competing plants and thus protect and / or increase yields from a qualitative and / or quantitative point of view. These herbicidal compositions clearly exceed the state of the art in terms of the properties mentioned.

[0364] Because of its weeding and plant growth regulating properties, these herbicidal compositions can be used to control harmful plants in crops of genetic modification or crops obtained by mutation / selection. These crops are usually distinguished by particularly favorable characteristics, such as resistance to herbicidal compositions or to plant diseases or plant disease pathogens such as specific insects or microorganisms such as fungi, bacteria or viruses. Other specific characteristics relate to the amount, quality, storability, composition and specific ingredients of the material of the results, for example. Therefore, for example, the transgenic plants whose starch content is known to increase or whose starch quality changes, or the materials of the results, have those with different fatty acid compositions.

[0365] A particular aspect of the invention also relates to a method for controlling unwanted vegetation, such as harmful plants, which comprises applying a herbicidal composition, preferably by the post-emergence method, to harmful or unwanted plants, parts of said harmful or unwanted plants, or to an area where harmful or unwanted plants grow, such as an area under cultivation.

[0366] In the context of the present invention, "control" means that the growth of one or more harmful plants is significantly reduced compared to untreated harmful plants. Preferably, the growth of one or more harmful plants is substantially reduced (60%-79%), more preferably, the growth of one or more harmful plants is largely or completely inhibited (80%-100%), and in particular, the growth of one or more harmful plants is almost completely or completely inhibited (90%-100%).

[0367] Thus, in a further aspect, the present invention relates to a method for controlling unwanted plant growth and / or controlling harmful plants, comprising the step of applying an aqueous spray liquor containing a combination of a herbicide and a copolymer CP, preferably in one of the preferred embodiments defined herein, to unwanted plants or harmful plants, parts of unwanted plants or harmful plants, or areas where unwanted plants or harmful plants grow.

[0368] The aqueous spray containing the combination of herbicide and copolymer CP can be used for controlling the undesirable vegetation in the killing program, in industrial vegetation management and forestry, in vegetables and perennial crops and in turf and lawn, wherein one or more herbicidal compositions can be applied before or after emergence, i.e. before, during and / or after the emergence of undesirable plants. Preferably, it is applied as post-emergence treatment, i.e. during and / or after the emergence of undesirable plants. Herein, one or more herbicidal compositions are applied to the place where the crops are planted before the crops are planted or emerge.

[0369] In industrial weed management and forestry, it is desirable to control large numbers of weeds for a longer period of time. It may also be desirable to control large weeds, or taller species such as shrubs or trees. Industrial weed management includes, for example, railroad and right-of-way management, fence lines and non-agricultural land such as industrial and building land, gravel areas, roads or sidewalks. Forestry includes, for example, the clearing of existing forests or bushes, the removal of regenerated vegetation after mechanical forest felling, or the management of weeds under forestry plantations. In the latter case, it may be desirable to protect the desired trees from contact with a spray solution containing the herbicidal mixture according to the invention.

[0370] Aqueous sprays containing a combination of herbicides and copolymers CP can also be used for weed control in turf and lawns, provided that the desired grass species tolerate the herbicidal composition. In particular, such herbicidal compositions can be used in desired grasses that have been rendered tolerant to the corresponding agrochemical active ingredients (e.g. glufosinate or its salts) by mutagenesis or genetic engineering.

[0371] Glufosinate and its salts are non-selective systemic herbicides with good post-emergence activity against a wide range of weeds and can therefore be used in pest control programmes, in industrial vegetation management and forestry, in vegetable and perennial crops and in turf and lawns.

[0372] Therefore, the present invention also relates to a method for killing unwanted vegetation in crops, which comprises applying an aqueous spray containing a combination of a herbicide and a copolymer CP to the site where the crop is to be planted before planting (or sowing) or emergence of the crop. Herein, the herbicidal composition is applied to the unwanted vegetation or its site.

[0373] The present invention also relates to a method for controlling undesirable vegetation, the method comprising applying an aqueous spray containing a combination of a herbicide and a copolymer CP to a site where undesirable vegetation is present or expected to be present. Application can be before, during and / or after the emergence of undesirable vegetation, preferably during and / or after the emergence of undesirable vegetation. In one embodiment, application is performed before crop emergence, and the crop is cultivated in a site where undesirable vegetation is present or expected to be present. In another embodiment, application is performed before planting crops.

[0374] In the killing program, spraying liquid can be before crop plant sowing (planting) or after crop plant sowing (or planting) but before crop plant emergence, particularly before sowing. Spraying liquid is preferably used before crop plant sowing. For killing, spraying liquid will usually be used before planting crops at most 9 months, often at most 6 months, preferably at most 4 months. Killing and using can be carried out on the date of 1 day before crop plant emergence, and preferably on the date before crop plant sowing / planting, preferably at least one day before planting, preferably at least 2 days and particularly at least 4 days date or 6 months to 1 day before emergence, particularly 4 months to 2 days before emergence and more preferably 4 months to 4 days before emergence. Of course, killing and using one or more times, for example once, twice, three times, four times or five times, can be repeated within this time frame.

[0375] The special benefit of the spraying liquid containing herbicide and copolymer CP is that the application of the spraying liquid provides very good post-emergence herbicide activity, that is, they show good herbicidal activity to the unwanted plants that are emerged. Therefore, in a preferred embodiment of the present invention, the spraying liquid is applied after the unwanted plants emerge, that is, during and / or after the emergence of unwanted plants. When the unwanted plants start from leaf development to flowering, it is particularly advantageous to apply the spraying liquid after emergence. The herbicidal composition is particularly useful for controlling the unwanted vegetation that has developed to a state that is difficult to control with conventional killing mixtures, that is, when the individual weeds are higher than 10 cm (4 inches) or even higher than 15 cm (6 inches) and / or for controlling heavy weed populations. In the case of post-emergence treatment of plants, the herbicidal composition is preferably applied by foliar application.

[0376] Spray liquors can be applied in a conventional manner using techniques familiar to the skilled person. Suitable techniques include spraying, atomizing, dusting, broadcasting or watering. The type of application depends in a well-known manner on the intended purpose; in any case, they should ensure the finest possible distribution of the active ingredient according to the invention.

[0377] In one embodiment, the spray liquor is applied to the locus mainly by spraying, especially foliar spraying, an aqueous dilution of the active ingredients of the mixture. Application can be carried out by conventional spraying techniques using a spray liquor amount of about 10 to 2000 l / ha or 50 to 1000 l / ha (e.g. 100 to 500 l / ha).

[0378] The desired application rate of the herbicidal active compound via the spray liquor depends on the density of the undesirable vegetation, the developmental stage of the plants, the climatic conditions of the site where the mixture is to be used and the method of application.

[0379] Typically, the application rate of L-glufosinate or its salt is generally 50 g / ha to 3000 g / ha and preferably in the range of 100 g / ha to 2000 g / ha or 200 g / ha to 1500 g / ha of active substance (ai).

[0380] Sprays containing copolymers CP and herbicides provide persistent herbicidal activity, even under adverse weathering conditions, which allows more flexible application in life-killing applications and minimizes the risk of weed escape. In addition, sprays containing copolymers CP and herbicides provide excellent crop compatibility with certain conventional crop plants and with herbicide-tolerant crop plants, i.e., their use in these crops results in reduced damage to crop plants and / or does not result in increased damage to crop plants. Therefore, sprays containing copolymers CP can also be applied after crop plants emerge. Sprays containing copolymers CP can also show an accelerating effect on harmful plants, i.e., they can affect the damage to harmful plants more quickly.

[0381] Spray solutions containing the copolymers CP are also suitable for controlling weeds which are resistant to customary herbicides, such as, for example, glyphosate-resistant weeds, weeds resistant to auxin inhibitor herbicides, such as 2,4-D or dicamba, weeds resistant to photosynthesis inhibitors, such as atrazine, weeds resistant to ALS inhibitors, such as sulfonylureas, imidazolinones or triazolopyrimidines, weeds resistant to ACCase inhibitors, such as clodinafop-butyl, clethodim or pinoxaden, or weeds resistant to protoporphyrinogen-IX-oxidase inhibitors, such as sulfentrazone, fluazifop-butyl, fomesafen or acifluorfen, for example, as listed in the International Weed Resistance Survey (IRWS). http: / / www.weedscience.org / Summary / SpeciesbySOATable.aspx) In particular, they are suitable for controlling resistant weeds resistant to glufosinate or its salts, such as those listed in the International Weed Resistance Survey, for example ACCase-resistant barnyard grass, wild oats (Avena fatua), large spike foxtail (Alopecurus myosuroides), bald barnyard grass (Echinochloa colona), Japanese foxtail (Alopecurus japonicus), dry brome (Bromus tectorum), barley grass (Hordeummurinum), field duckbill (Ischaemum rugosum), foxtail (Setaria viridis), stone grass (Sorghumhalepense), foxtail (Alopecurusaequalis), Apera spica-venti, false wild oats (Avena sterilis), beckmannia szygachne, double male brome (Bromus diandrus), crabgrass (Digitaria sanguinalis), Echinocloa oryzoides, Echinochloaphyllopogon, Phalaris minor, Phalaris paradoxa, Setaria faber, Setaria, Brachypodium distachyon, Bromus sterilis, Cynosurus echinatus, Digitaria insularis, Digitaria ischaemum, Leptochloachinensis, Phalaris brachystachis, Rotboellia cochinchinensis, Digitaria ciliaris, Ehrharta longiflora, Eriochloa punctata), Leptochloa panicoides, Lolium persicum, Polypogon fugax, Sclerochloa kengiana, Snowdenia polystacha, Sorghumsudanese, and Brachiariaplantaginea; ALS inhibitor-resistant barnyard grass, Poa annua, wild oats, big spike foxtail, bald barnyard grass, green spike amaranth (Amaranthus hybridus), long-horned amaranth (Amaranthus palmeri), western amaranth (Amaranthus rudis), Sumatran wine grass (Conyza sumatrensis), retroflexus amaranth (Amaranthus retroflexus), ragweed (Ambrosia artemisifolia), Canada weed (Conyza canadensis), Kochia scoparia, wild radish (Raphanus raphanistrum), spring radish (Senecio vernalis), Japanese foxtail, Bidens pilosa, dry brome, quinoa (Chenopodium album), fragrant silk grass (Conyza bonariensis), barley grass, field duckbill (Ischaemum rugosum), European groundsel (Senecio vulgaris), Setaria, Sisymbrium orientale, Sphagnum sphaerocephala, Amaranthus blitum, Amaranthus powellii, Apiraea, Oats, Brassica rapa, Bromus diandrus, Descurainia sophia, Crabgrass, Echinochloa oryzoides, Echinochloa phyllopogon, Orangutan, Lactuca serriola, Phalaenopsis sphaerocephala, Setaria faberi, Setaria, Sinapis arvensis, Solanum ptycanthum, Sonchus oleraceus, Stellaria media, Amaranthus blitoides), Amaranthus spinosus, Amaranthus viridis, Ambrosia trifida, Bidens subalternans, Bromus spp., Bromus spp., Capsella bursa-pastoris, Centaurea cyanus, Cynosurusechinatus), Cyperus difformis, Fimbristilis miliacea, Galeopsis tetrahit, Galium aparine, Galium spurium, Helianthus annuus, Hirschfeldia incana, Limnocharis flava, Limnophila erecta, Papaver rhoeas, Parthenium hysterophorus, Phalaris brachystachis, Polygonum convolvulus, Polygonum lapathifolium, Polygonumpersicaria, Ranunculus acris, Rottboellia cochinchinensis, Sagittaria montevidensis), Salsola tragus, Schoenoplectus mucronatus, Setaria pumila, Sonchus asper, Xanthium strumarium, Ageratum conyzoides, Alisma canaliculum, Alisma plantago-aquatica, Ammannia auriculata, Ammannia coccinea, Ammannia arvensis, Anthemis cotula, Bacopa rotundifolia, Bifora radians, Blyxa aubertii, Brassica tournefortii, Bromus japonicus, Bromus serrata, secalinus), Lithospermum arvense, Camelina microcarpa, Chamaesycemaculata), Chrysanthemum coronarium, Clidemia hirta, Crepis tectorum, Cuscuta pentagona, Cyperus brevifolis, Cyperus compressus, Cyperus esculentus, Cyperus iria, Cyperus odoratus, Damasonium minus, Diplotaxis erucoides, Diplotaxis tenuifolia, Dopatrum junceum, Echium plantagineum, Elatine triandra, Eleocharis acicularis, Erucaria hispanica, Erysimum repandum), Galiumtricornutum, Iva xanthifolia, Ixophorus unisetus, Lamiumamplexicaule, Limnophilia sessiliflora, Linderniadubia, Lindernia micrantha, Lindernia procumbens, Ludwigia prostrata, Matricaria recutita, Mesembryanthemumcrystallinum, Monochoria korsakowii, Monochoria vaginalis, Myosoton aquaticum, Neslia paniculata, Oryza sativavar.sylvatica, Pentzia suffruticosa, Picris hieracioides), radish (Raphanussativus), shepherd's purse (Rapistrum rugosum), shepherd's purse (Rorippa indica),indica), Rotalapusilla, Rumex dentatus, Sagittaria guayensis, Sagittaria pygmaea, Sagittaria trifolia, Schoenoplectus fluviatilis, Schoenoplectus juncoides, Schoenoplectus wallichii, Sida spinosa, Silenegallica, Sinapisalba, Sisymbrium thellungii, Sorghumbicolor, Spergula arvensis, Thlaspi arvense, Tripleurospermum perforatum, Vaccaria hispanica and Vicia sativa; photosynthesis inhibitor resistant barnyard grass, bluegrass, big spike foxtail, bald barnyard, green spike amaranth, long-horned amaranth, western amaranth, Sumatran white wine grass, retroflex amaranth, ragweed, Canada grass, Kochia, wild radish, spring groundsel (Senecio vernalis), Japanese foxtail, Bidens pilosa, Bromus chinensis, Chenopodium album, fragrant silk grass, field duckbill, European groundsel, Setaria viridis, oriental garlic mustard, concave head amaranth, Bower amaranth, Apira grass, weed, chicken feather vegetable, crabgrass, white gorilla grass, small phalaenopsis, strange phalaenopsis, big foxtail, setaria, wild mustard, oriental nightshade (Solanum ptycanthum), chickweed, North American amaranth, wrinkled fruit amaranth, South American Bidens pilosa, two spike short-spoulate grass, shepherd's purse, mengren grass (Chloris barbata), Cyperus rotundus, Echinochloa erecta, Epilobium ciliatum, Polygonum aviculare, Polygonum aviculare, Polygonum truncatum, Polygonum sempervirens, Polygonum sempervirens, Purslane, Schoenoplectus mucronatus, Setaria pumila, Solanum nigrum, Sonchus asper, Urochloa panicoides, Vulpia bromoides, Abutilon theophrasti, Amaranthus albus, Amaranthus sempervirens,cruentus), Arabidopsis thaliana, Arenaria serpyllifolia, Bidens tripartita, Chenopodium ficifolium, Chenopodium polyspermum, Crypsis schoenoides, Datura stramonium, Epilobium tetragonum, Galinsogaciliata, Matricaria discoidea, Panicum capillare, Panicum dichotomiflorum, Plantago lagopus, Polygonum hydopiper, Polygonum pensylvanicum, Polygonum monspeliensis), Rostraria, smyrnacea, Rumex acetosella, Setaria verticillata, and Urtica urens; PS-I-electron conductance inhibitor-resistant bluegrass, sumatrae, Canada grass, Japanese foxtail, Bidens pilosa, fragrant silk grass, barley grass, field duckbill, Amaranthus chinensis, Solanum ptycanthum, Arctotheca calendula, North American willow herb, Hedyotis verticillata, Solanum nigrum, European foxtail fescue (Vulpia bromoides), field bindweed (Convolvulus arvensis), wild chrysanthemum (Crassocephalum crepidioides), Cuphea carthagensis, Erigeron philadelphicus, Gamochaeta pensylvanica, Landoltia punctata, Lepidium virginicum, Mazus fauriei, Mazus pumilus, Mitracarpus hirtus, Sclerochloadura, Solanum americanum, and Youngiajaponica; glyphosate-resistant bluegrass, barnyardgrass, green amaranth, long-horned amaranth, western amaranth, sumatrae, ragweed, Canada grass, kochia, wild radish, bidens, fragrant silk grass, barley grass, stone grass, chicken feather vegetable, two-sex brome, wild lettuce, chicory, spiny amaranth, three-lobed ragweed, crabgrass, rough ear grass (Hedyotisverticillata), sunflower, silver guayule (Parthenium hysterophorus), long-leaf plantain (Plantagolanceolata), tumbleweed (Salsola tragus), millet tail grass (Urochloa panicoides), arm grass (Brachiaria eruciformis), red brome (Bromus rubens), tall tiger tail grass (Chloris elata), truncated tiger tail grass (Chloris truncata), tiger tail grass (Chloris virgata), Cynodon hirsutus, Lactuca saligna, Leptochloa virgata, Paspalum paniculatum, and Tridax procumbens; microtubule assembly inhibitor-resistant barnyard grass, bluegrass, wild oats, large-spiked alopecuroides, long-horned amaranth, foxtail grass, stone grass, alopecuroides, sedge grass, and dense blue pansy (Fumaria densiflora); auxin herbicide-resistant barnyard grass, bald barnyard grass, green amaranth, western amaranth, white wine grass, Kochia scoparia, wild radish, chenopodimalbum, oriental garlic mustard, sow's wormwood, wild lettuce, wild mustard, chicory, chickweed, Arctotheca calendula, cornflower (Centaurea cyanus), crabgrass, Fimbristylis miliacea, weasel flower, original ragwort, ragwort, Hirschfeldia incana, yellow rush (Limnocharis flava), upright yellow rush (Limnocharis erecta), poppy, long-leaved plantain, buttercup (Ranunculus acris), musk thistle (Carduus nutans), carduus pycnocephalus, yellow knapweed (Centaureasoltitialis), multi-spotted knapweed (Centaurea stoebe ssp.Micranthos), prickly lettuce (Cirsiumarvense), bamboo vegetable (Commelina diffusa), peacock barnyard (Echinochloacrus-pavonis, Soliva sessilis, and Sphenoclea zeylanica; HPPD inhibitor-resistant Amaranthus palmeri and Amaranthus occidentalis; PPO inhibitor-resistant Acalypha australis, Amaranthus nigra, Amaranthus palmeri, Amaranthus retroflexus, Amaranthus occidentalis, Ambrosia ragweed, Avena sativa, Descurainia sophia, Acalypha sutchuenensis, and Seneciovernalis; carotenoid biosynthesis inhibitor-resistant Hydrilla verticillata, wild radish, Senecio vernalis, and oriental garlic mustard; VLCFA inhibitor-resistant Alopecurus macrostachya, Avena sativa, and Echinochloa crus-galli.

[0382] Examples

[0383] The present invention is explained in more detail by means of the following examples.

[0384] The following abbreviations are used:

[0385] 2-PH-2EO-SO3 2-propylheptyl ether sulfate ammonium salt with 2EO

[0386] 2-EH-2EO-SO3 Ammonium salt of 2-ethylhexyl ether sulfate with 2EO

[0387] 2-PH-SO3 2-Propylheptyl sulfate ammonium salt

[0388] 2-PH-0.88PO-3.523EO-SO3 2-propylheptyl ether sulfate ammonium salt with 3.523EO and 0.88PO (Lutensol XL40)

[0390] 2-PH-1.873PO-1.253EO-SO3 2-propylheptyl ether sulfate ammonium salt with 1.253EO and 1.873PO

[0391] 2-PH-0.78PO-2.7EO-SO3 Ammonium salt of 2-propylheptyl ether sulfate with 2.7EO and 0.78PO

[0392] EO Ethyleneoxy (=CH2CH2O)

[0393] PO 1,2-propyleneoxy (=CH2CH(CH3)O)

[0394] SLES Sodium Lauryl Ether Sulfate

[0395] Glufosinate racemate D-Glufosinate racemate and L-Glufosinate racemate

[0396] SL Water Soluble Concentrate Formulations

[0397] Sodium 2-ethylhexyl sulfate was used as a 25% by weight aqueous solution.

[0398] The alkyl ether sulfate of formula (I) (ammonium salt of 2-propylheptyl ether sulfate, 2-PH-2EO-SO3) and other adjuvants (ammonium salts of 2-EH-2EO-SO3 and PH-SO3) are used as aqueous concentrates.

[0399] The herbicide compounds (glufosinate and the racemate of L-glufosinate, respectively) were used as aqueous solutions (TC) of the corresponding glufosinate salts at the given concentrations.

[0400] The improving effect of the alkyl ether sulfates of formula (I) on the herbicides according to the invention was demonstrated by the following greenhouse experiments, which are referred to below as "inventive examples" (IE).

[0401] For comparison, two different types of comparative examples were performed. In the first type of comparative example (CE1), only the herbicide compound was applied without any adjuvant. In the second type of comparative example (CE2), the herbicide compound was applied together with the ammonium salt of 2-propylheptyl sulfate (2-PH-SO3), 2-ethylhexyl ether sulfate (2-EH-2EO-SO3), sodium 2-ethylhexyl sulfate (commercially available as Texapon EHS) and sodium lauryl ether sulfate (SLES), which are used as adjuvants, but not according to formula (I).

[0402] All details concerning the applied alkyl ether sulfates of formula (I), herbicide compounds and comparative adjuvants are summarized below.

[0403]

[0404]

[0405] TC = mother drug

[0406] Greenhouse research is carried out to evaluate the influence of the weed control efficacy of glufosinate-ammonium on the alkyl ether sulfates and other adjuvants with formula (I). The seedlings of grass plants (AVEFA, ECHCG, DIGSA and SETVI) and broadleaf weeds (KCHSC, CHEAL, AMAPA, AMATA and ABUTH) are grown to a height of 3 to 20 cm in a 10×10×10 cm pot filled with sandy planting soil (Limburgerhofsoil), which height depends on plant habit. The glufosinate-ammonium ammonium is applied after emergence in the corresponding application rate given in the following table individually or in combination with the corresponding adjuvants of different amounts to treat weeds.

[0407] For this purpose, the herbicide formulations and the corresponding adjuvants were introduced into tap water to obtain the spray liquor. All mixtures resulted in stable, clear spray solutions. The spray liquor was then applied to the plants using a sprayer (XR Teejet 110015) at a spray rate of 200 l / ha.

[0408] The test period lasts for 21 days. During this time, the plants are tended and their response to the treatment with the active compounds is evaluated.

[0409] The evaluation of the damage caused by the chemical composition is carried out using a scale of 0 to 100% compared to untreated control plants. Here, 0 means no damage and 100 means complete destruction of the plant.

[0410] Plants used in the greenhouse experiments belonged to the following species:

[0411] scientific name Code Common name Ramie ABUTH Velvetleaf Wild Oats AVEFA Wild Oats Quinoa CHEAL Lambsquarter Crataegus DIGSA Big crabgrass Echinochloa crus-galli ECHCG Barnyardgrass barley HORVW winter barley Kochia KCHSC Kochia Setaria SETVI Green foxtail Palmer amaranth AMAPA Palmer amaranth Tuberous Amaranth (Amaranthus x tamariscinus) AMATA Common water hemp Barley (Spring) HORVS Spring Barley Soft wheat (spring) TZAS spring wheat Amaranthus tuberculatus AMATU Amaranthus

[0412] Average values ​​of AVEFA, ECHCG, DIGSA, and SETVI

[0413] Average of KCHSC, CHEAL, AMAPA, AMATA and ABUTH

[0414] The results are summarized in the following Tables 1 to 15, which show the application doses of the individual active substances in grams of active ingredient per hectare (g ai / ha). The herbicidal activity of the individual active substances and their combinations in post-emergence application was evaluated 14 days and 28 days after treatment (DAT), respectively.

[0415]

[0416]

[0417]

[0418]

[0419]

[0420]

[0421]

[0422]

[0423]

[0424]

[0425]

[0426]

[0427]

[0428]

[0429]

[0430]

[0431]

[0432]

[0433]

[0434]

Claims

1. Use of at least one compound of formula (I) for improving the herbicidal effect of one or more herbicidal compounds, [R-O-(A-O) n -SO3] - M + (I) in M + It is a cation; A is C2-C3 alkanediyl; R is branched C 10 -alkyl; and n is an integer ranging from 1 to 10.

2. A method for controlling undesirable vegetation, wherein at least one compound of the formula (I) according to claim 1 and at least one herbicide compound are applied to the undesirable vegetation or their habitat.

3. The use or method according to any one of the preceding claims, wherein: R is 2-propylheptyl.

4. The use or method according to any one of the preceding claims, wherein: R is an isodecyl group having at least one methyl group bonded to a tertiary carbon atom of R.

5. The use or method according to any one of the preceding claims, wherein: The cation M + is monovalent and is selected from the group consisting of: alkali metal ions, NH4 + and H 4-m NR 1 m + , where R 1 Selected from the group consisting of: alkyl, which is optionally substituted by hydroxy, methoxy, amino, alkylamino or dialkylamino, cycloalkyl, (Alk-NR')BN(R")2, (CH2CH2O) k CH2CH2OH and (CH2CH(CH3)O) n CH2CH(CH3)OH, wherein n is 0, 1 or 2, k is 0, 1 or 2, Alk is alkylene, B is alkylene, R' is hydrogen or alkyl, R" is hydrogen or alkyl, and m is an integer ranging from 1 to 4.

6. The use or method according to claim 5, wherein: M + It is a sodium cation.

7. The use or method according to claim 5, wherein: M + Yes H 4-m NR 1 m + , where m is 1, 2, or 3.

8. The use or method according to claim 7, wherein R 1 is selected from the group consisting of an alkyl group substituted with 1 hydroxyl group or 1 methoxy group, and m is an integer in the range of 1, 2 or 3.

9. The use or method according to any one of the preceding claims, wherein: The numerical average of n is in the range of 1.1 to 7.0, preferably in the range of 1.5 to 6.0, more preferably in the range of 1.7 to 5.

0.

10. The use or method according to any one of the preceding claims, wherein: A is CH2CH2, or a combination of CH2CH2 and CH2CH(CH3).

11. The use or method according to any one of the preceding claims, wherein: The herbicide compound is at least one herbicide compound selected from Groups (a) to (o): (a) herbicidal compounds from the group of glutamine synthetase inhibitors; (b) herbicidal compounds from the group of enolpyruvylshikimate 3-phosphate synthase inhibitors (EPSP inhibitors); (c) herbicidal compounds from the group of acetolactate synthase inhibitors (ALS inhibitors); (d) herbicidal compounds from the group of protoporphyrinogen-IX oxidase inhibitors; (e) herbicidal compounds from the group of auxin herbicides and auxin transport inhibitors; (f) herbicide compounds from the group of photosynthesis inhibitors; (g) herbicidal compounds from the group of lipid biosynthesis inhibitors (acetyl-CoA carboxylase inhibitors, ACCase inhibitors); (h) lipid biosynthesis inhibitors other than ACCase inhibitors; (i) bleaching agent herbicides; (j) 7,8-dihydropteroate synthase inhibitors (DHP inhibitors); (k) mitotic inhibitors; (l) Very long chain fatty acid synthesis inhibitors (VLCFA inhibitors); (m) cellulose biosynthesis inhibitors; (n) Decoupler herbicides; (o) other herbicides selected from the group consisting of: brombutyric acid chloranil, chloranil methyl, cyproconazole, benzylpyrasulfuron, cyprosulfuron and its salts and esters, dalapon, dazomethanil, diazepam, diazepam-methyl sulfonate, thiamethoxam, DSMA, cyproconazole, cyprothiocarb and its salts, ethoprop, chloranil, chloranil-isopropyl ester, chloranil-methyl ester, chloranil-M-isopropyl ester, chloranil-M-methyl ester Ester, chlorpyrifos, chlorpyrifos-butyl, furafil, cypermethrin, chlorpyrifos ammonium, indole, maleic hydrazide, fluazifop, metamifop, isoxathiapiprolin, methyl azide, methyl bromide, methyl-chlorpyrifos, methyl iodide, MSMA, oleic acid, oxazithromycin, nonanoic acid, chlorpyrifos, chlorpyrifos-butyl, fluazifop, chlorpyrifos, and 6-chloro-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (CAS 499223-49-3) and its salts and esters, and 6-chloro-4-(2,7-dimethyl-1-naphthyl)-5-hydroxy-2-methyl-pyridazin-3-one (CAS 2414510-21-5) (HST inhibitor; FMC).

12. The use or method according to any one of the preceding claims, wherein: The herbicide compound comprises the herbicide compound of group (a), which is particularly selected from the group consisting of glufosinate, glufosinate salts and combinations thereof.

13. The use or method according to claim 12, wherein: The herbicidal compound comprises at least one additional herbicidal compound selected from the groups (b) to (o) as defined in claim 11 .

14. The use or method according to any one of the preceding claims, wherein: The weight ratio of the compound of formula (I) to the herbicide compound is in the range of 1:10 to 10:

1.

15. The use or method according to any one of the preceding claims, wherein: The compound of formula (I) and the herbicide compound are tank mixed.

16. A herbicidal formulation comprising i. at least one compound of formula (I) according to the definition in any one of claims 1 to 10; as well as ii. at least one herbicide compound.

17. The herbicidal formulation according to claim 16, wherein The formulation is a soluble liquid (SL) formulation.

18. An aqueous spray liquid comprising i. at least one compound of formula (I) according to the definition in any one of claims 1 to 10; and ii. at least one herbicide compound.

Images