Compositions comprising mesosulfuron and tehp

Abstract

The present invention is in the field of crop protection and relates primarily to certain herbicidally active compositions comprising mesosulfuron and tris(2-ethylhexyl)phosphate (TEHP), which can be used to combat harmful plants, such as crop plants, in the field. The invention also relates to corresponding methods and uses of these compositions.

Description

[0001] This invention belongs to the field of crop protection technology and mainly relates to certain herbicidal active compositions comprising mesosulfuron-methyl and tris(2-ethylhexyl) phosphate (TEHP), which can be used to combat harmful plants, such as crops, in the field. This invention also relates to corresponding methods and uses of these compositions.

[0002] These herbicides are highly effective against harmful plants in crops, but their effectiveness often depends on the application rate, the formulation involved, the harmful plant or the spectrum of harmful plants to be controlled, the crop, and climatic conditions. In some cases, one or more safeners are useful or even necessary to improve herbicide selectivity in certain crops. However, overall, there remains a need for compositions and methods that achieve herbicidal action with low application rates of the active compound. Lower application rates not only reduce the amount of active compound required for application but also typically reduce the amount of formulation adjuvants required. This reduces both economic inputs and improves the ecocompatibility of herbicide treatments.

[0003] WO 95 / 10507 discloses mesosulfuron, its esters and salts, and their use as herbicides and / or plant growth regulators.

[0004] WO 98 / 24320 relates to herbicidal products comprising mesosulfuron, its esters and salts, and one or more other herbicides.

[0005] WO 03 / 073854 and WO 2015 / 01881 teach certain ternary combinations of the sulfonylurea herbicides mesosulfuron-methyl, iosulfuron-methyl, and other herbicides.

[0006] WO 00 / 56146 and WO 01 / 47356 disclose surfactant-solvent systems having certain types of phosphates as solvents for preparing compositions containing one or more herbicidal active ingredients.

[0007] WO 2006 / 034817 relates to agricultural chemical compositions containing phosphate esters having at least one branched alkyl group.

[0008] WO 2008 / 074406 mentions a method of using tris(butoxyethyl) phosphate (TBEP) to enhance the penetration of active ingredients from herbicide and / or safener groups.

[0009] WO 2009 / 100846 teaches a herbicidal agricultural chemical composition containing a specific combination of herbicides and certain phosphates, suitable for controlling unwanted plants in sugar beet crops.

[0010] WO 2008 / 049618, WO 2008 / 092615 and WO 2012 / 152527 each disclose compositions based on cyclophosphamide and certain adjuvants, optionally containing additional components such as safeners or co-herbicides.

[0011] WO 2010 / 122313 relates to alcohol alkoxylates as adjuvants to agricultural chemical formulations, and reports the herbicidal efficacy of oxychloride or nicosulfuron in the presence of said alcohol alkoxylates compared to known adjuvants such as tris(2-ethylhexyl) phosphate (TEHP).

[0012] WO 2013 / 087395 relates to the use of aromatic phosphate esters as adjuvants in agricultural chemical formulations.

[0013] WO 2014 / 060557 relates to certain liquid herbicidal compositions comprising a C1-C6 alkyl methacrylate polymer thickener and a solvent system containing certain alcohol solvents and heavy aromatic hydrocarbon solvents. Preferably, the compositions disclosed in WO 2014 / 060557 comprise built-in phosphoric acid and / or phosphonic acid adjuvants.

[0014] One possibility for improving the application properties of herbicides is to combine the herbicidal active compound with one or more other active compounds and / or with one or more adjuvants that can improve the properties of the herbicidal active compound, such as biological, chemical and / or physical properties.

[0015] However, the combined use of multiple compounds can lead to physical and biological incompatibility. What is needed are combinations or compositions of compounds with favorable activity properties, high stability, and (if possible) improved herbicidal action.

[0016] Surprisingly, certain compositions containing mesosulfuron-methyl and tris(2-ethylhexyl) phosphate (TEHP) have been found to work together in a particularly advantageous manner, for example, when used in crop plants suitable for their selective use, with the addition of a safer where appropriate.

[0017] Therefore, the present invention provides a concentrated herbicide composition (hereinafter referred to as the "composition") comprising a herbicide-effective amount of component (A), wherein

[0018] (A) Methyl disulfuron and / or its salts representing formula (I)

[0019]

[0020] (B) indicates tris(2-ethylhexyl) phosphate (TEHP).

[0021] And preferably one or more additional components selected from components (C) and components (D):

[0022] (C) One or more additional herbicides selected from the following:

[0023] (C1) Iodosulfuron and its salts, (C2) Thiazolylsulfuron and its salts, (C3) Acrylsulfuron and its salts, (C4) Formamidesulfuron and its salts, (C5) Probenzylsulfuron and its salts, and (C6) Pyrfluthrin.

[0024] (D) One or more safety agents,

[0025] The weight ratio of the total amount of component (A) to the total amount of component (B) is in the range of 1:2 to 1:100, based on the total weight of the composition.

[0026] Herbicidal compositions containing sulfonylurea herbicides such as mesosulfuron and / or its salts are typically combined with adjuvants in a spray can, which result in improved performance, particularly improved biological properties, of the spray solution compared to a spray solution without the adjuvants. Adjuvants commonly used in canning mixtures with mesosulfuron and / or its salts are vegetable oils or their methyl esters (e.g., rapeseed oil methyl ester, Mero) or one or more alkali metal lauryl ether sulfates (e.g., sodium lauryl ether sulfate, which may be used as...). Available for retail sale.

[0027] It has been found that similar improvements in performance for mesosulfuron and / or its salts can be obtained when tris(2-ethylhexyl) phosphate (TEHP) is used instead of these adjuvants. Furthermore, it has been found that the amount of TEHP required to achieve these improvements is much lower, for example, than that required for vegetable oils or their methyl esters. While the amount of adjuvants (e.g., rapeseed oil methyl ester) in such cases is typically about 1 kg or 2 kg per hectare, a suitable amount of TEHP can be as low as 100 g per hectare (100 g / ha).

[0028] Furthermore, at the same application rate, the effect observed with tris(2-ethylhexyl) phosphate (TEHP) was superior to that obtained with the structurally similar adjuvant tris(butoxyethyl) phosphate (TBEP).

[0029] Furthermore, it was found that the amount of TEHP used in spray mixtures should not exceed a certain level or concentration, as this leads to significant and undesirable phytotoxic effects on crop plants. In experiments using 2 kg TEHP per hectare, significant phytotoxic effects were observed in crop plants such as wheat (e.g., soft wheat (winter) TRZAW), indicating that the crop damage caused by the combination of TEHP with mesosulfuron-methyl and / or its salts was too high and unacceptable.

[0030] The compositions of the present invention are preferably free of (i.e., do not contain) cyclophosphamide, and are preferably free of C1-C6 alkyl methacrylates.

[0031] In the herbicide concentrated composition of the present invention, preferably components (A) and (C) are the only herbicides present in the composition, that is, the herbicide concentrated composition of the present invention preferably does not contain any herbicides other than those defined by components (A) and (C).

[0032] In the herbicide concentrated composition of the present invention, in each case, based on the total weight of the composition, the weight ratio of the total amount of component (A) to the total amount of component (B) is preferably in the range of 1:3 to 1:100, more preferably in the range of 1:4 to 1:100, and even more preferably in the range of 1:4 to 1:80.

[0033] In the herbicide concentrated composition of the present invention, in each case, based on the total weight of the composition, the weight ratio of the total amount of component (A) to the total amount of component (B) is preferably in the range of 1:4 to 1:60, more preferably in the range of 1:4 to 1:50, even more preferably in the range of 1:4 to 1:40, or in the range of 1:5 to 1:30.

[0034] In the herbicide concentrated composition of the present invention, in each case, based on the total weight of the composition, the total amount of component (A) is preferably 0.5% to 6% by weight, more preferably 1% to 5% by weight, and more preferably 2% to 4.5% by weight.

[0035] In the herbicide concentrated composition of the present invention, in each case, based on the total weight of the composition, the total amount of component (B) is preferably 10% to 50% by weight, preferably 15% to 45% by weight, and more preferably 20% to 40% by weight.

[0036] The herbicide concentrate composition of the present invention preferably comprises, in each case, a total amount of 0.5% to 6% by weight of component (A) and a total amount of 10% to 50% by weight of component (B) based on the total weight of the composition; more preferably, it comprises a total amount of 1% to 5% by weight of component (A) and a total amount of 15% to 45% by weight of component (B); and particularly preferably, it comprises a total amount of 2% to 4.5% by weight of component (A) and a total amount of 20% to 40% by weight of component (B).

[0037] Herbicides and safeners used and defined as components (A), (C), and (D) in the context of this invention are known in themselves and are described in particular in "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and the references therein. Herbicides used in the context of this invention are described in more detail below.

[0038] In the context of this invention, the terms “other herbicides,” “other herbicidal active ingredients,” and “other agrochemically active compounds” refer to the herbicides and agrochemically active compounds (insecticides) listed in “The Pesticide Manual,” 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012, and particularly relate to herbicides and agrochemically active compounds (insecticides) other than the compounds of components (A), (C), and (D) as defined in the context of this invention.

[0039] In the context of this invention, if the abbreviated form of the common name of the active compound is used—unless otherwise specifically indicated—it in each case includes all common derivatives, such as esters and salts, and isomers, particularly optical isomers, especially one or more commercially available forms. In the case of sulfonamides such as sulfonylureas, the salt also includes salts formed by cation exchange of hydrogen atoms on the sulfonamide group.

[0040] Components (A) and (B) used in the context of this invention, as well as optional components (C) and (D), are known in themselves.

[0041] Component (A): Methyl disulfuron (IUPAC-name: 2-[(4,6-dimethoxypyrimidin-2-ylcarbamoyl)aminosulfonyl]-α-methanesulfonylamino-p-toluic acid, CAS Registry No. 400852-66-6) and Methyl disulfuron (IUPAC-name: 2-[(4,6-dimethoxypyrimidin-2-ylcarbamoyl)aminosulfonyl]-α-(methanesulfonylamino)-p-toluate methyl ester, CAS Registry No. 208465-21-8).

[0042] Component (A): Methyl disulfuron and its salts are known and described, for example, in WO 95 / 10507A1.

[0043] Component (A) of the herbicide concentrate composition according to the present invention preferably consists of mesosulfuron-methyl and / or sodium mesosulfuron-methyl.

[0044] Component (B): Tris(2-ethylhexyl) phosphate (TEHP) (CAS Registry No. 78-42-2) is known and used as a plasticizer, flame retardant, and solvent. TEHP is used, for example, as... TOF (Lanxess) is commercially available.

[0045] The herbicide concentrate composition of the present invention may contain component (C) which is composed of herbicides selected from components (C1) to (C6).

[0046] Component (C1): Iosulfuron (IUPAC nomenclature: 4-iodo-2-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoylaminosulfonyl]benzoic acid, CAS Registry No. 185119-76-0), its esters and its salts are known and described, for example, in WO 92 / 13845A1.

[0047] Preferably, in the context of this invention, component (C1) comprises or is composed of iodosulfuron-methyl (IUPAC-name: methyl 4-iodo-2-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoylaminosulfonyl]benzoate, CAS Registry No. 144550-06-1) and / or sodium iodosulfuron-methyl (IUPAC-name: ({[5-iodo-2-(methoxycarbonyl)phenyl]sulfonyl}carbamoyl)(4-methoxy-6-methyl-1,3,5-triazin-2-yl)imine (azanide) sodium, CAS Registry No. 144550-36-71).

[0048] Component (C2): Thionesulfuron (IUPAC-Nomenclature: 4-[(4,5-dihydro-3-methoxy-4-methyl-5-oxo-1H-1,2,4-triazol-1-yl)carbonylaminosulfonyl]-5-methylthiophene-3-carboxylic acid, CAS Registry No. 936331-72-5, its esters and its salts are known and described, for example, in WO 01 / 05788.

[0049] Preferably, in the context of this invention, component (C2) comprises thiazosulfonyl ester (IUPAC nomenclature: 4-[(4,5-dihydro-3-methoxy-4-methyl-5-oxo-1H-1,2,4-triazol-1-yl)carbonylaminosulfonyl]-5-methylthiophene-3-carboxylic acid methyl ester, CAS Registry No. 317815-83-1) or has the following composition.

[0050] Component (C3): Acrylsulfuron, its esters and its salts are known and described, for example, in EP 0 131 258A2.

[0051] Preferably, in the context of this invention, component (C3) comprises acylsulfamethoxypyrimidin-2-yl)-3-methanesulfonyl(methyl)aminosulfonylurea, CAS Registry No. 120923-37-7 and / or its sodium salt, i.e. acylsulfamethoxypyrimidin-2-yl)-3-methanesulfonyl(methyl)aminosulfonylurea, or is composed of the same.

[0052] Component (C4): Formamide sulfonamide and its salts are known and described, for example, in EP 0 757679A1.

[0053] Preferably, in the context of this invention, component (C4) comprises or consists of formamide sulfonamide (IUPAC nomenclature: 1-(4,6-dimethoxypyrimidin-2-yl)-3-[2-(dimethylcarbamoyl)-5-carbamoylbenzenesulfonyl]urea, CAS Registry No. 173159-57-4) and / or its sodium salt, i.e., sodium formamide sulfonamide, or thereof. When sodium formamide sulfonamide is used in crystalline form, the form described in WO 2016 / 096613 is preferred.

[0054] Component (C5): Propanesulfuron and its salts are known and described, for example, in EP 0 507171A1 and US 5,534,486 A.

[0055] Preferably, in the context of this invention, component (C5) comprises methyl propenzamide (IUPAC nomenclature: methyl 2-[(4,5-dihydro-4-methyl-5-oxo-3-propoxy-1H-1,2,4-triazol-1-carbamoyl)sulfonyl]benzoate, CAS Registry No. 145026-81-9) and / or its sodium salt, namely sodium propenzamide (CAS Registry No. 181274-15-7), or is composed of the same.

[0056] Component (C6): Pyrfluthrin (IUPAC nomenclature: 2′,4′-difluoro-2-(α,α,α-trifluoro-m-tolyloxy)nicotinamide, CAS Registry No. 83164-33-4) is known and described, for example, in EP 0 053 011A1 and US 4,618,366 A.

[0057] For the use of component (A) (and optionally component (C)) of the compositions of the present invention, depending on the plant crop, it is advantageous to apply a safener to reduce or avoid potential damage to the crop. Examples of suitable safeners are those that have a safener effect when combined with sulfonylurea herbicides, preferably phenylsulfonylureas. Suitable safeners are disclosed, for example, in WO-A-96 / 14747 and the documents cited therein.

[0058] Component (D) consists of ingredients that act as safeners in monocotyledonous crops. Safeners suitable for use as component (D) in the context of this invention are known in themselves and are described, for example, on page 87, line 21 to page 100, line 25 of WO 2013 / 092500A1 and the references therein.

[0059] The following compounds are examples of safeners for the appropriate component (D) of the above-mentioned herbicidal active component (A):

[0060] a) Compounds of the dichlorophenylpyrazoline-3-carboxylic acid type, preferably compounds such as ethyl 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylic acid (pyrazoline), as described in, for example, the relevant compounds in WO 91 / 07874.

[0061] b) Dichlorophenylpyrazole carboxylic acid derivatives, preferably compounds such as ethyl 1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate, ethyl 1-(2,4-dichlorophenyl)-5-isopropylpyrazole-3-carboxylate, ethyl 1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)pyrazole-3-carboxylate, ethyl 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate, and related compounds as described in EPA 333 131 and EP A 269 806.

[0062] c) Triazole carboxylic acid compounds, preferably compounds such as oxazol, i.e., ethyl 1-(2,4-dichlorophenyl)-5-trichloromethyl(1H)-1,2,4-triazole-3-carboxylate, and related compounds (see EP-A-174 562 and EP-A-346 620).

[0063] d) Compounds of the 5-benzyl or 5-phenyl-2-isooxazoline-3-carboxylic acid type or 5,5-diphenyl-2-isooxazoline-3-carboxylic acid type, preferably compounds such as ethyl 5-(2,4-dichlorobenzyl)-2-isooxazoline-3-carboxylic acid (or ethyl 5-phenyl-2-isooxazoline-3-carboxylic acid) and related compounds described in, for example, WO 91 / 08202, or ethyl 5,5-diphenyl-2-isooxazoline-3-carboxylic acid (ethyl bisphenyloxazolate) or propyl 5,5-diphenyl-2-isooxazoline-3-carboxylic acid or ethyl 5-(4-fluorophenyl)-5-phenyl-2-isooxazoline-3-carboxylic acid, as described in patent application (WO A 95 / 07897).

[0064] e) Compounds of the 8-quinoline glyoxylic acid type, preferably

[0065] 1-Methylhexyl-1-yl(5-chloro-8-quinolinoxy)acetate (Xylocarboxylic acid ester),

[0066] (1,3-Dimethylbut-1-yl)(5-chloro-8-quinolinoxy)acetate,

[0067] 4-Allyloxybutyl(5-chloro-8-quinolinoxy)acetate,

[0068] 1-Allyloxy-2-yl(5-chloro-8-quinolinoxy)acetate,

[0069] Ethyl (5-chloro-8-quinolinoxy)acetate

[0070] (5-chloro-8-quinolinoxy)methyl acetate,

[0071] (5-Chloro-8-quinolinoxy)allyl acetate,

[0072] 2-(2-Propyliminooxy)-1-ethyl(5-chloro-8-quinolinoxy)acetate,

[0073] 2-Oxypropen-1-yl(5-chloro-8-quinolinoxy)acetate,

[0074] And related compounds as described in EP-A-86 750, EP-A-94 349 and EP-A-191 736 or EP-A-0 492 366.

[0075] f) Compounds of the (5-chloro-8-quinolinoxy)malonic acid type, preferably compounds such as diethyl (5-chloro-8-quinolinoxy)malonate, diallyl (5-chloro-8-quinolinoxy)malonate, methyl ethyl (5-chloro-8-quinolinoxy)malonate, and related compounds as described in EP-A-0 582 198.

[0076] g) Phenoxyacetic acid, phenoxypropionic acid or aromatic carboxylic acid type active compounds, such as 2,4-dichlorophenoxyacetic acid (2,4-D) and its esters, 4-chloro-2-methylphenoxypropionic acid (methylchloropropionic acid), MCPA or 3,6-dichloro-2-methoxybenzoic acid (dicamba) and its esters.

[0077] The component (D) of the herbicide concentrate composition according to the invention is preferably selected from: (D1) pyrazole oxalic acid, its ester and / or its salt (preferably pyrazole ethyl oxalate), (D2) bis(oxazolyl) acid, its ester and / or its salt (preferably bis(oxazolyl) ethyl oxalate), (D3) cyclopropanesulfonamide, its ester and / or its salt (preferably cyclopropanesulfonamide), (D4) oxalic acid, its ester and / or its salt (preferably oxalate ester), (D5) oxazolyl sulfadiazine, its ester and / or its salt (preferably oxazolyl sulfadiazine), and (D6) oxazolyl sulfadiazine, its ester and / or its salt (preferably oxazolyl sulfadiazine).

[0078] In the herbicide concentrate composition according to the invention, if present, the safener of component (D) is preferably selected from: (D1) pyrazole oxalic acid, its ester and / or its salt (preferably pyrazole ethyl oxalate), (D2) bis(oxazolyl) acid, its ester and / or its salt (preferably bis(oxazolyl) ethyl oxalate), (D3) cyclopropanesulfonamide, its ester and / or its salt (preferably cyclopropanesulfonamide), (D4) oxalic acid, its ester and / or its salt (preferably oxalate ester), (D5) oxazolyl sulfadiazine, its ester and / or its salt (preferably oxazolyl sulfadiazine), and (D6) oxazolyl sulfadiazine, its ester and / or its salt (preferably oxazolyl sulfadiazine).

[0079] The particularly preferred components (D) are components (D1) to (D4):

[0080] Component (D1): Pyrazolium oxalate (IUPAC nomenclature: (RS)-1-(2,4-dichlorophenyl)-5-methyl-2-pyrazolium-3,5-dicarboxylic acid, CAS Registry No. 135591-00-3) and pyrazolium oxalate (IUPAC nomenclature: (RS)-1-(2,4-dichlorophenyl)-5-methyl-2-pyrazolium-3,5-dicarboxylic acid diethyl ester, CAS Registry No. 135590-91-9).

[0081] Typically, the safener pyrazole herbicides, as component (D), exhibits excellent efficacy when combined with components (A) and (B) of the present invention.

[0082] Component (D1): Pyrazole oxalic acid, its esters and / or salts are known and described, for example, in WO 91 / 07874A1.

[0083] Component (D2): Bisbenoxazolic acid (IUPAC nomenclature: 4,5-dihydro-5,5-diphenyl-1,2-oxazol-3-carboxylic acid, CAS Registry No. 209866-92-2) and ethyl bisbenoxazolic acid (IUPAC nomenclature: ethyl 4,5-dihydro-5,5-diphenyl-1,2-oxazol-3-carboxylic acid, CAS Registry No. 163520-33-0).

[0084] Component (D2): Bisbenoxazolic acid, its esters and / or salts are known and described, for example, in WO 95 / 07897A1.

[0085] Component (D3): Cyclopropanesulfonamide (IUPAC nomenclature: N-[4-(cyclopropylcarbamoyl)phenylsulfonyl]-2-methoxybenzamide, CAS Registry No. 221667-31-8).

[0086] Component (D3): Cyclopropanesulfonamide, its esters and / or salts are known and described, for example, in WO 99 / 16744A1.

[0087] Component (D4): oxalic acid (IUPAC name: (5-chloroquinoline-8-yloxy)acetic acid, CAS Registry No. 88349-88-6) and oxalic acid ester (IUPAC name: ((RS)-1-methylhexyl(5-chloroquinoline-8-yloxy)acetic acid ester, CAS Registry No. 99607-70-2).

[0088] Component (D4): Oxalic acid, its esters and / or salts are known and described, for example, in US 4,881,966A.

[0089] In the context of this invention, the salts of the compounds of components (A), (C) and (D) are preferably in the form of the corresponding alkali metal salt, alkaline earth metal salt or ammonium salt, more preferably in the form of the corresponding alkali metal salt, more preferably in the form of the corresponding sodium salt or potassium salt, and most preferably in the form of the corresponding sodium salt.

[0090] The herbicide concentrate composition according to the invention comprises a herbicidally effective amount of component (A), and may also contain other ingredients in addition to component (B), such as different types of agrochemically active compounds and / or formulation adjuvants and / or additives commonly used in crop protection, or may be used in conjunction with these.

[0091] In a preferred embodiment, the composition according to the invention has improved effects. From both an economic and ecological perspective, the improved effects allow for reduced application amounts of individual active compounds, more effective action at the same application amount, control of species that have been previously uncontrollable (active gaps), extended application periods, and / or reduced number of individual applications required, resulting in a more advantageous weed control system for the user.

[0092] The application rate of the herbicide concentrate composition of the present invention can vary depending on the time requirements, the specific weeds to be controlled, and the crop. Typically, the application rate of the herbicide concentrate composition of the present invention results in an application rate of component (A) of 0.5 to 50 g / ha, preferably 1 to 25 g / ha, more preferably 2 to 20 g / ha. A particularly preferred application rate of component (A) of the present invention is found to be 5 to 16 g / ha, typically in the range of 5 to 12 g / ha.

[0093] The herbicide concentrated compositions of the present invention are preferably in formulations selected from emulsifiable concentrates (EC), oil dispersions (OD), and wettable granules (WG). Particularly preferred are the herbicide concentrated compositions of the present invention in oil dispersion (OD) form.

[0094] Advantageously, the herbicide concentrate composition of the present invention comprises one or more safeners, preferably one or more safeners selected from the following: (D1) pyrazole oxalic acid, its ester and / or its salt (preferably pyrazole ethyl oxalate), (D2) bis(oxazolyl) acid, its ester and / or its salt (preferably bis(oxazolyl) ethyl oxalate), (D3) cyclopropanesulfonamide, its ester and / or its salt (preferably cyclopropanesulfonamide), (D4) oxalic acid, its ester and / or its salt (preferably oxalate ester), (D5) oxazolyl sulfadiazine, its ester and / or its salt (preferably oxazolyl sulfadiazine), and (D6) oxazolyl sulfadiazine, its ester and / or its salt (preferably oxazolyl sulfadiazine).

[0095] Advantageously, the herbicide concentrate composition of the present invention comprises one or more additional herbicides selected from (C1) to (C6) as defined herein.

[0096] Preferably, the herbicide concentrate composition of the present invention comprises one or more additional herbicides selected from (C1) to (C6) as defined herein and one or more safeners.

[0097] Preferably, the herbicide concentrated composition of the present invention comprises:

[0098] One or more of the following additional herbicides: (C1) iodosulfuron and its salts, (C2) thiamethoxam and its salts, (C5) propanil and its salts, and (C6) pyrifluquinazon.

[0099] and / or

[0100] (D) One or more safeners selected from the following: (D1) pyrazole oxalic acid, its ester and / or its salt (preferably pyrazole ethyl oxalate), (D2) bis(oxazolyl) acid, its ester and / or its salt (preferably bis(oxazolyl) ethyl oxalate), (D3) cyclopropanesulfonamide, its ester and / or its salt (preferably cyclopropanesulfonamide), (D4) oxalic acid, its ester and / or its salt (preferably oxalate ethyl oxalate), (D5) oxazolyl sulfadiazine, its ester and / or its salt (preferably oxazolyl sulfadiazine), and (D6) oxazolyl sulfadiazine, its ester and / or its salt (preferably oxazolyl sulfadiazine).

[0101] Preferably, the herbicide concentrated composition of the present invention comprises:

[0102] One or more of the following additional herbicides: (C1) iodosulfuron and its salts, (C2) thiamethoxam and its salts, (C5) propanil and its salts, and (C6) pyrifluquinazon.

[0103] and / or

[0104] (D) One or more of the following safeners: (D1) pyrazosulfuron, (D2) ethyl bis(oxazolyl) ester, (D3) cyclopropanesulfonamide, (D4) pyrazosulfuron, (D5) pyrazosulfuron and (D6) pyrazosulfuron.

[0105] More preferably, the herbicide concentrated composition of the present invention comprises:

[0106] One or more of the following additional herbicides: (C1) iodosulfuron or its sodium salt, (C2) thiamethoxam or its sodium salt, and (C6) pyrifluquinazon.

[0107] and

[0108] One or more of the following safeners: (D1) pyrazolium bromide, (D2) ethyl bis(oxazolyl) ester, (D3) cyclopropanesulfonamide, (D4) pyrazolium bromide and (D6) pyrazolium bromide.

[0109] Particularly preferred are the herbicide concentrated compositions according to the invention, wherein the safener is (D1) pyrazosulfuron, (D2) ethyl bis(oxazolyl) ester or (D3) cyclopropanesulfonamide.

[0110] Particularly preferred are the herbicide concentrate compositions according to the invention, wherein one or more additional herbicides are (C1) iodosulfuron or its sodium salt and / or (C2) thiamethoxam or its sodium salt.

[0111] In the presence of (C1) iodosulfuron or its salt in the herbicide concentrate composition according to the invention, the weight ratio between components (A) and (C1) is preferably in the range of 8:1 to 1:1, more preferably in the range of 5:1 to 1:1, and even more preferably in the range of 3:1 to 1:1.

[0112] In the presence of (C2) thiamethoxam or a salt thereof in the herbicide concentrate composition according to the invention, the weight ratio between components (A) and (C2) is preferably in the range of 5:1 to 1:2, more preferably 4:1 to 1:1, and even more preferably 3:1 to 1:1.

[0113] When a safer (D) is present in the herbicide concentrate composition according to the invention, the weight ratio of the total amounts of component (A) and component (D) is preferably 1:1 to 1:6, more preferably 2:3 to 1:5, and even more preferably 1:2 to 1:4. Particularly when the safer is (D1) pyrazosulfuron, the particularly preferred weight ratio of the amounts of component (A) and component (D1) is preferably in the range of 2:5 to 1:4.

[0114] The herbicide concentrate composition according to the invention can be used with other agrochemically active compounds (e.g., in combination as a tank mix) or with formulation adjuvants and additives commonly used in crop protection. Additives include, for example, fertilizers and colorants. In each case, the amounts, ratios, and application rates, as well as the ranges for application rates described above, are preferred.

[0115] Although the compositions according to the invention exhibit outstanding herbicidal activity against both monocot and dicot weeds, crop plants are damaged only to a lesser extent (if any), particularly if one or more safeners (as component (D) of the compositions of the invention) are used.

[0116] Furthermore, some compositions according to the invention possess outstanding growth-regulating properties on crop plants. They participate in plant metabolism in a regulatory manner and can therefore be used to induce directional effects on plant components and promote harvesting, for example, by triggering dehydration and dwarfing growth. In addition, they are suitable for overall control and suppression of undesirable vegetative growth without simultaneously damaging the plant. Suppression of vegetative growth is crucial in a large number of monocotyledonous and dicotyledonous crops because it can thereby reduce or completely prevent yield losses due to lodging.

[0117] Due to their weed-controlling and plant growth-regulating properties, the compositions according to the invention can be used to control harmful plants in genetically modified crop plants or crop plants obtained through mutation / selection. These crop plants are generally distinguished by particularly advantageous properties, such as resistance to weed-controlling compositions or resistance to plant diseases or pathogens of plant diseases (e.g., specific insects or microorganisms, such as fungi, bacteria, or viruses). Other specific properties relate to, for example, the quantity, quality, storability, composition, and specific components of the harvested material. Thus, for example, transgenic plants known to have increased starch content or altered starch quality, or those from which the harvested material has a different fatty acid composition.

[0118] Conventional methods for producing novel plants with altered properties compared to those previously known include, for example, traditional breeding methods and the generation of mutants (see, for example, US 5,162,602; US 4,761,373; US 4,443,971). Alternatively, novel plants with altered properties can be produced by means of recombinant methods (see, for example, EP-A-0221044, EP-A-0131624). Several cases are described below, for example:

[0119] - Modifying crop plants using recombinant technologies aims to alter the synthesis of starch in the plant (e.g., WO 92 / 11376, WO 92 / 14827, WO 91 / 19806).

[0120] - Genetically modified crops that exhibit resistance to other herbicides, such as sulfonylureas (EP-A-0257993, US-A-5013659).

[0121] - Transgenic crop plants capable of producing Bacillus thuringiensis toxin (Bt toxin), which confer resistance to certain pests (EP-A-0142924, EP-A-0193259).

[0122] - A transgenic crop plant with altered fatty acid composition (WO 91 / 13972).

[0123] Many techniques in molecular biology are known in principle, which can be used to produce novel transgenic plants with altered properties: see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed., Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; or Winnacker, Gene und Klone, VCH Weinheim, 2nd ed., 1996; or Christou, Trends in Plant Science, 1 (1996) 423-431.

[0124] To perform such recombination operations, nucleic acid molecules that allow for mutagenesis or sequence alteration through DNA sequence recombination can be introduced into plasmids. For example, the standard methods described above allow for base exchange, removal of subsequences, or addition of natural or synthetic sequences. To link DNA fragments together, adaptors or linkers can be added to the fragments.

[0125] For example, the generation of plant cells with reduced gene product activity can be achieved by expressing at least one corresponding antisense RNA, sense RNA for achieving a co-inhibitory effect, or by expressing at least one appropriately constructed ribosome that specifically cleaves the transcript of the aforementioned gene product.

[0126] For this purpose, DNA molecules covering the complete coding sequence of the gene product (including any flanking sequences that may be present) or only covering a portion of the coding sequence, which must be long enough to have an antisense effect in the cell, can be used. Alternatively, DNA sequences that are highly homologous to the coding sequence of the gene product but not identical to it can also be used.

[0127] When nucleic acid molecules are expressed in plants, the synthesized proteins can be located in any desired compartment of the plant cell. However, to achieve localization in a specific compartment, the coding region can be linked, for example, to a DNA sequence that ensures localization in that specific compartment. Such sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J.11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J.1 (1991), 95-106).

[0128] Transgenic plant cells can be regenerated using known techniques to produce complete plants. In principle, transgenic plants can be any desired plant species, meaning they can be both monocots and dicots. Therefore, it is possible to obtain transgenic plants whose properties are altered through the overexpression, elimination, or repression of homologous (=natural) genes or gene sequences, or through the expression of heterologous (=exogenous) genes or gene sequences.

[0129] Therefore, the present invention also relates to a method for controlling undesirable vegetation (e.g., harmful plants), preferably in plant crops such as cereals (e.g., wheat, barley, rye, oats, and their hybrids such as black wheat, rice, corn, millet), sugar beets, sugarcane, rapeseed, cotton, and soybeans, particularly preferably in monocotyledonous crops such as cereals (e.g., wheat, barley, rye, oats, and their hybrids such as black wheat, rice, corn, and millet), comprising, for example, applying a composition (i.e., a herbicide concentrate composition or a tank-mixed composition) as defined in the context of the present invention to plants, such as harmful plants, parts of these plants, plant seeds, or areas of plant growth, such as cultivated areas, by pre-emergence methods, post-emergence methods, or pre-emergence and post-emergence methods, wherein the amount of component (A) applied is preferably in the range of 0.5 to 50 g / ha, more preferably in the range of 1 to 25 g / ha, and particularly preferably in the range of 2 to 20 g / ha. It has been found that a particularly preferred application rate of component (A) of the present invention is in the range of 5 to 16 g / ha, and typically in the range of 5 to 12 g / ha.

[0130] Plant crops are preferably tolerant to acetolactate synthase (ALS) inhibitors and can be acquired through genetic modification or mutational selection.

[0131] This invention also relates to the use of herbicide concentrated compositions or tank-mixed compositions as defined in the context of this invention for controlling harmful plants, preferably harmful plants in plant crops, wherein the application rate of component (A) is preferably in the range of 0.5 to 50 g / ha, more preferably in the range of 1 to 25 g / ha, and particularly preferably in the range of 2 to 20 g / ha. Particularly preferred application rates of component (A) of this invention are found to be in the range of 5 to 16 g / ha, and generally in the range of 5 to 12 g / ha.

[0132] The compositions according to the invention can also be used non-selectively to control unwanted vegetation, for example in crop planting, roadside areas, squares, industrial plants, or railway facilities.

[0133] Herbicide concentrate compositions as defined in the context of this invention can be combined with other agrochemically active compounds, additives and / or conventional formulation adjuvants and then applied as a water dilution in a conventional manner, but can also be applied as a so-called tank-mix composition or tank mixture by co-diluting the different components with water before application to undesirable vegetation (and optionally crop plants).

[0134] The herbicide concentrate compositions according to the present invention can be formulated in various ways according to current biological and / or chemo-physical parameters. Examples of general possibilities for formulations are as follows: wettable powder (WP), water-soluble concentrate, emulsifiable concentrate (EC), aqueous solution (SL), emulsion (EW) such as oil-in-water and water-in-oil emulsions, sprayable solutions or emulsions, suspension concentrate (SC), oil dispersion (OD), oil-based or water-based dispersion, suspension emulsion, powder (DP), seed dressing, granules or water-dispersible granules (WG) for soil application or broadcasting, ULV formulations, microcapsules, or waxes.

[0135] Individual formulation types are known in principle and are described, for example, in: Winnacker-Küchler, "Chemische Technologie", Vol. 7, C. Hauser Verlag Munich, 4th ed., 1986; van Valkenburg, "Pesticide Formulations", Marcel Dekker NY, 1973; K. Martens, "Spray Drying Handbook", 3rd ed., 1979, G. Goodwin Ltd., London.

[0136] The required formulation adjuvants, such as inert substances, surfactants, solvents, and other additives, are also known and described, for example, in Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd ed., Darland Books, Caldwell NJ; HvOlphen, "Introduction to Clay Colloid Chemistry", 2nd ed., J. Wiley & Sons, Marsden, NY; "Solvents Guide", 2nd ed., Interscience, NY 1950; McCutcheon's, "Detergents and Emulsifiers Annual", MCPubl. Corp., Ridgewood NJ; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., NY 1964; " "[Surface-active ethylene oxide adducts], Wiss. Verlagsgesellschaft, Stuttgart 1976, Winnacker-Küchler, "Chemische Technologie", Volume 7, C. Hauser Verlag Munich, 4th edition 1986.

[0137] Based on these formulations, combinations with other agricultural chemically active substances (such as other herbicides, fungicides, or insecticides) and with (additional) safeners, fertilizers, and / or growth regulators can also be prepared, for example, in the form of pre-mixed or tank-mixed products.

[0138] Wettable powders (sprayable powders) are products that can be uniformly dispersed in water and, in addition to active compounds, contain ionic or nonionic surfactants (wetting agents, dispersants), such as polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols or fatty amines, alkyl sulfonates or alkylbenzene sulfonates, sodium lignosulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate or sodium oleoylmethyl taurate, as well as diluents or inert substances.

[0139] Emulsifiable concentrates are prepared by dissolving an active compound in an organic solvent, such as butanol, cyclohexanone, dimethylformamide, xylene, or other high-boiling aromatics or hydrocarbons, and adding one or more ionic or nonionic surfactants (emulsifiers). Examples of emulsifiers that can be used are: calcium salts of alkyl aryl sulfonic acids, such as calcium dodecylbenzene sulfonate, or nonionic emulsifiers, such as fatty acid polyethylene glycol esters, alkyl aryl polyethylene glycol ethers, fatty alcohol polyethylene glycol ethers, propylene oxide / ethylene oxide condensates, alkyl polyethers, sorbitol fatty acid esters, polyoxyethylene sorbitol fatty acid esters, or polyoxyethylene sorbitol esters.

[0140] Powders are obtained by grinding active compounds together with finely ground solid materials such as talc, natural clays such as kaolin, bentonite, and pyrophyllite or diatomaceous earth.

[0141] Suspension concentrates (SCs) can be water-based or oil-based. They can be prepared, for example, by wet milling using a commercially available bead mill, and, if appropriate, by adding additional surfactants such as those mentioned above in the cases of other formulation types.

[0142] Emulsions, such as oil-in-water emulsions (EW), can be prepared, for example, by means of a stirrer, colloid mill and / or static mixer, using an aqueous organic solvent and, where appropriate, additional surfactants as mentioned in the cases of other formulation types above.

[0143] Granules can be prepared by spraying an active compound onto an absorbent granular inert material or by applying a concentrate of the active compound onto the surface of a carrier (e.g., sand, kaolin, or granular inert material) using a binder (e.g., polyvinyl alcohol, sodium polyacrylate, or mineral oil). Suitable active compounds can also be granulated in conventional methods for producing fertilizer granules, if desired, in mixtures with fertilizers. Typically, water-dispersible granules are prepared by conventional methods such as spray drying, fluidized bed granulation, disc granulation, mixing with a high-speed mixer, and extrusion without solid inert material. For information on the generation of disc pellets, fluidized bed pellets, extruder pellets, and spray pellets, see, for example, the methods in "Spray-Drying Handbook," 3rd ed., 1979, G. Goodwin Ltd., London; J.E. Browning, "Agglomeration," Chemical and Engineering, 1967, page 147 et seq.; and "Perry's Chemical Engineer's Handbook," 5th ed., McGraw-Hill, New York, 1973, pp. 8-57.

[0144] For more details on crop protection product formulations, see, for example, G.K. Lingmam, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pp. 81-96 and JD. F. Reyer, S.A. Vans, "Weed Control Handbook", 5th edition, Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.

[0145] Depending to some extent on the formulation type, the herbicide concentrate composition according to the invention preferably further comprises one or more additional components selected from other formulation adjuvants and additives commonly used in crop protection, preferably selected from components (E) to (G) and optionally component (H):

[0146] (E) Surfactant, preferably in a total amount of 0.1% to 60% by weight, more preferably in a total amount of 5% to 40% by weight, and even more preferably in a total amount of 10% to 30% by weight.

[0147] (F) Water, preferably in a total amount of 0.1% to 30% by weight.

[0148] (G) Organic solvent, preferably in a total amount of 0.1% to 20% by weight.

[0149] (H) Other formulation adjuvants (component (H)) that are different from components (B), (E), (F) and (G), preferably in a total amount of 0.1% to 50% by weight.

[0150] Based on the total weight of the composition in each case.

[0151] In a preferred embodiment, the herbicide concentrate composition according to the present invention comprises:

[0152] Component (A), in total amount from 0.5% to 6% by weight, preferably from 1% to 5% by weight, more preferably from 2% to 4.5% by weight.

[0153] Component (B), in a total amount of 10% to 50% by weight, preferably 15% to 45% by weight, more preferably 20% to 40% by weight.

[0154] And one, two, three or more additional components selected from components (C) to (H): other herbicides (component (C)), in a total amount of 0.5% to 12% by weight.

[0155] Safety agent (component (D)), in total amounts of 0.75% to 15% by weight.

[0156] Surfactant (component (E)), in a total amount of 0.1% to 60% by weight, preferably 5% to 40% by weight, more preferably 10% to 30% by weight.

[0157] Water (component (F)), in total amounts from 0.1% to 30% by weight.

[0158] Organic solvent (component (G)), in total amounts from 0.1% to 20% by weight.

[0159] Other formulation adjuvants (component (H)) that are different from components (B), (E), (F) and (G) are present in a total amount of 0.1% to 50% by weight.

[0160] Based on the total weight of the composition in each case.

[0161] In a preferred embodiment, the herbicide concentrate composition according to the present invention comprises:

[0162] Component (A), in total amount from 0.5% to 6% by weight, preferably from 1% to 5% by weight, more preferably from 2% to 4.5% by weight.

[0163] Component (B), in a total amount of 10% to 50% by weight, preferably 15% to 45% by weight, more preferably 20% to 40% by weight.

[0164] One or more safety agents (component (D)) in total amounts from 0.75% to 15% by weight.

[0165] and one, two, three or more other components selected from components (C) and (E) through (H).

[0166] Other herbicides (component (C)), in total amounts from 0.5% to 12% by weight.

[0167] Surfactant (component (E)), in a total amount of 0.1% to 60% by weight, preferably 5% to 40% by weight, more preferably 10% to 30% by weight.

[0168] Water (component (F)), in total amounts from 0.1% to 30% by weight.

[0169] Organic solvent (component (G)), in total amounts from 0.1% to 20% by weight.

[0170] Other formulation adjuvants (component (H)) that are different from components (B), (E), (F) and (G) are present in a total amount of 0.1% to 50% by weight.

[0171] Based on the total weight of the composition in each case.

[0172] In a preferred embodiment, the herbicide concentrate composition according to the present invention comprises:

[0173] Component (A), in total amount from 0.5% to 6% by weight, preferably from 1% to 5% by weight, more preferably from 2% to 4.5% by weight.

[0174] Component (B), in a total amount of 10% to 50% by weight, preferably 15% to 45% by weight, more preferably 20% to 40% by weight.

[0175] Other herbicides (component (C)), in total amounts from 0.5% to 12% by weight.

[0176] One or more safety agents (component (D)) in total of 2% to 15% by weight.

[0177] and one, two, three or more other components selected from components (E) to (H).

[0178] Surfactant (component (E)), in a total amount of 0.1% to 60% by weight, preferably 5% to 40% by weight, more preferably 10% to 30% by weight.

[0179] Water (component (F)), in total amounts from 0.1% to 30% by weight.

[0180] Organic solvent (component (G)), in total amounts from 0.1% to 20% by weight.

[0181] Other formulation adjuvants (component (H)) that are different from components (B), (E), (F) and (G) are present in a total amount of 0.1% to 50% by weight.

[0182] Based on the total weight of the composition in each case.

[0183] In a preferred embodiment, the herbicide concentrate composition according to the present invention comprises:

[0184] Component (A), in a total amount of 1% to 5% by weight, more preferably 2% to 4.5% by weight.

[0185] Component (B), in a total amount of 15% to 45% by weight, more preferably 20% to 40% by weight.

[0186] Other herbicides (component (C)), in total amounts from 0.5% to 12% by weight.

[0187] One or more safety agents (component (D)) in total of 2% to 15% by weight.

[0188] and one, two, three or more other components selected from components (E) to (H).

[0189] Surfactant (component (E)), in a total amount of 0.1% to 60% by weight, preferably 5% to 40% by weight, more preferably 10% to 30% by weight.

[0190] Water (component (F)), in total amounts from 0.1% to 30% by weight.

[0191] Organic solvent (component (G)), in total amounts from 0.1% to 20% by weight.

[0192] Other formulation adjuvants (component (H)) that are different from components (B), (E), (F) and (G) are present in a total amount of 0.1% to 50% by weight.

[0193] Based on the total weight of the composition in each case.

[0194] In a preferred embodiment, the herbicide concentrate composition according to the present invention comprises:

[0195] Component (A), in total amount from 2% to 4.5% by weight.

[0196] Component (B), in total amount of 20% to 40% by weight

[0197] Other herbicides (component (C)), in total amounts from 0.5% to 12% by weight.

[0198] One or more safety agents (component (D)) in total of 5% to 15% by weight.

[0199] and one, two, three or more other components selected from components (E) to (H).

[0200] Surfactant (component (E)), in a total amount of 0.1% to 60% by weight, preferably 5% to 40% by weight, more preferably 10% to 30% by weight.

[0201] Water (component (F)), in total amounts from 0.1% to 30% by weight.

[0202] Organic solvent (component (G)), in total amounts from 0.1% to 20% by weight.

[0203] Other formulation adjuvants (component (H)) that are different from components (B), (E), (F) and (G) are present in a total amount of 0.1% to 50% by weight.

[0204] Based on the total weight of the composition in each case.

[0205] The concentration of the active compound in wettable powders is, for example, about 10% to 95% by weight, with the remainder to 100% by weight consisting of conventional formulation components. In the case of emulsifiable concentrates, the concentration of the active compound can be, for example, 5% to 80% by weight. In most cases, powder formulations contain 5% to 20% by weight of the active compound, and sprayable solutions contain about 0.2% to 25% by weight of the active compound. In the case of granules, such as dispersible granules, the active compound content depends in part on whether the active compound is present in liquid or solid form, and on which granulation aids and fillers are used. Typically, in the case of water-dispersible granules, the content is 10% to 90% by weight.

[0206] In addition, if appropriate, the above-mentioned active compound formulations may contain conventional binders, wetting agents, dispersants, emulsifiers, preservatives, antifreeze agents, solvents, fillers, colorants, carriers, defoamers, evaporation inhibitors, pH adjusters, or viscosity adjusters.

[0207] The herbicidal effect of the herbicide concentrate composition according to the invention can be improved, for example, by a surfactant, preferably by a wetting agent selected from fatty alcohol polyethylene glycol ethers. The fatty alcohol polyethylene glycol ether preferably contains 10-18 carbon atoms in the fatty alcohol group and 2-20 ethylene oxide units in the polyethylene glycol ether moiety. The fatty alcohol polyethylene glycol ether can be nonionic or ionic, for example, in the form of fatty alcohol polyethylene glycol ether sulfate, which can be used, for example, as an alkali metal salt (e.g., sodium or potassium salt) or ammonium salt, but can also be used as an alkaline earth metal salt such as magnesium salt, such as C 12 / C 14 Sodium diethylene glycol sulfate (DED) LRO (Clariant); see, for example, EP-A-0476555, EP-A-0048436, EP-A-0336151 or US-A-4,400,196, and Proc. EWRS Symp. "Factors Affecting Herbicidal Activity and Selectivity", 227-232 (1988). Nonionic fatty alcohol glycol ethers are, for example, those containing 2-20, preferably 3-15, ethylene oxide units (C... 10 -C 18 )-, preferred (C 10 -C 14 - Fatty alcohol glycol ethers (e.g., isotracene glycol ether), for example from Series, such as X-030 X-060 X-080 or X-150 (all from Clariant GmbH).

[0208] This invention further encompasses the combination of the herbicide concentrate composition of this invention with the aforementioned wetting agent selected from fatty alcohol polyglycol ethers, preferably containing 10-18 carbon atoms in the fatty alcohol group and 2-20 ethylene oxide units in the polyglycol ether moiety, and may exist in a nonionic or ionic form (e.g., as a fatty alcohol polyglycol ether sulfate). Preferably, C... 12 / C 14 Sodium diethylene glycol sulfate (DED) LRO (Clariant); and isotridecyl alcohol polyglycol ethers having 3-15 ethylene oxide units, for example from LRO, Cl ... X series, such as X-030 X-060 X-080 or X-150 (all from Clariant GmbH). It is also known that fatty alcohol glycol ethers, such as nonionic or ionic fatty alcohol glycol ethers (e.g., fatty alcohol glycol ether sulfate), are suitable as penetrants and activity enhancers for many other herbicides, especially those derived from imidazolinones (see, for example, EP-A-0502014).

[0209] Preferably, one or more surfactants (component (E)) are selected from castor oil ethoxylates, alkyl sulfosuccinates, polyhydroxy fatty acids and polyethylene glycol mono(tristyrylphenyl) ether.

[0210] Preferred herbicide concentrate compositions according to the present invention comprise one or more compounds selected from castor oil ethoxylates, C1-C 12 -alkyl sulfonyl succinate, polyhydroxy C 12 -C 22 - A surfactant (component (E)) of fatty acids and polyethylene glycol mono(tristyrenephenyl) ether.

[0211] Preferably, one or more surfactants (component (E)) are selected from castor oil ethoxylate (10EO), castor oil ethoxylate (40EO), sodium 2-ethylhexyl sulfosuccinate, polyhydroxy stearic acid, and polyethylene glycol mono(tristyrylphenyl) ether (16EO).

[0212] In the preferred herbicide concentrate composition according to the invention, in each case, the total amount of nonionic surfactant is at least 2% by weight, preferably at least 3% by weight, and more preferably at least 4% by weight, based on the total weight of the composition.

[0213] In a preferred embodiment, the composition according to the invention comprises at least one castor oil ethoxylate selected from castor oil ethoxylate having 5-50 ethylene oxide (EO) units in the polydiol ether portion, more preferably castor oil ethoxylate (10EO) and / or castor oil ethoxylate (40EO), wherein, in each case, the total amount is preferably at least 3% by weight, more preferably at least 4% by weight, based on the total weight of the composition.

[0214] In some preferred embodiments, the composition according to the invention comprises at least one constituent ionic surfactant selected from sulfosuccinates, preferably comprising or composed of sodium 2-ethylhexylsulfosuccinate. If a sulfosuccinate such as sodium 2-ethylhexylsulfosuccinate is present in the composition according to the invention, it is preferably present in a total amount of at least 3% by weight, more preferably at least 4% by weight, based on the total weight of the composition in each case.

[0215] In a preferred embodiment, the composition according to the invention comprises at least one nonionic surfactant and one ionic surfactant, wherein in each case, the total amount of the nonionic surfactant to the ionic surfactant is preferably in the range of 3:1 to 1:3 based on the total weight of the composition, and more preferably in the range of 2:1 to 1:2 based on the total weight of the composition. Preferably, the ratio of the total amount of nonionic surfactant to the total amount of ionic surfactant is in the range of 2:1 to 1:1 based on the total weight of the composition, and more preferably the ratio is greater than 1:1, i.e., the amount of nonionic surfactant is preferably slightly higher than the amount of ionic surfactant. In the preferred embodiment, the nonionic surfactant is preferably selected from castor oil ethoxylates having 5-50 ethylene oxide units in the polydiol ether portion, more preferably castor oil ethoxylate (10EO) and / or castor oil ethoxylate (40EO), and the ionic surfactant is selected from sulfosuccinates, and preferably sodium 2-ethylhexylsulfosuccinate.

[0216] The organic solvent that can be used as component (G) in the herbicide concentrated composition of the present invention is preferably selected from isobornyl acetate and propylene carbonate.

[0217] Isoborneol acetate can be used as an organic solvent (component (G)) in the herbicide concentrate composition of the present invention. If present, the total amount of isoborneol acetate is preferably in the range of 10% to 40% by weight based on the total weight of the herbicide concentrate composition according to the present invention.

[0218] The preferred organic solvent (component (G)) in the herbicide concentrate composition according to the invention is propylene carbonate. If present, the total amount of propylene carbonate is preferably in the range of 0.1% to 10% by weight, based on the total weight of the herbicide concentrate composition according to the invention.

[0219] The formulation adjuvant (component (H)) in the herbicide concentrate composition according to the present invention is preferably selected from C. 16 -C 22 C1-C4 alkyl esters of fatty acids, C 10 -C 22 Fatty alcohol ethoxylated ethers, thickeners, and pH adjusters (pH buffers).

[0220] The compositions according to the invention preferably contain at least one formulation adjuvant. In one specific aspect, the compositions according to the invention contain one or more C... 16 -C 22 C1-C4 alkyl esters of fatty acids, preferably at least one C 16 -C 22 Fatty acid methyl esters, more preferably monounsaturated C 16 -C 22 Methyl esters of fatty acids. Particularly preferred are compositions according to the invention comprising methyl cis-9-octadecenoate (methyl oleate) (which is commercially available, for example, as Radia 7066).

[0221] In the preferred herbicide concentrated compositions according to the invention, C is calculated based on the total weight of the composition in each case. 16 -C 22 The total amount of C1-C4 alkyl esters of fatty acids is at least 5% by weight, preferably at least 10% by weight.

[0222] In the preferred herbicide concentrate compositions according to the invention, in each case, based on the total weight of the composition, the monounsaturated C 16 -C 22 The total amount of fatty acid methyl esters, especially methyl cis-9-octadecenoate (methyl oleate), is at least 10% by weight, preferably at least 15% by weight, and more preferably at least 20% by weight.

[0223] In the preferred herbicide concentrate compositions according to the invention, in each case, based on the total weight of the composition, the monounsaturated C 16 -C 22 The total amount of fatty acid methyl esters, especially methyl cis-9-octadecenoate (methyl oleate), is 10% to 50% by weight, preferably 15% to 45% by weight, and more preferably 20% to 40% by weight.

[0224] When the composition according to the invention is applied post-emergence to winter wheat (TRZAW), it is comparable to commercially available herbicides. (Mesosulfuron-methyl + Thiamethoxam + Pyrazosulfuron-methyl WG (45+15+112.5g / kg)) and Compared to combinations containing sodium lauryl ether sulfate, it showed similar crop safety (crop damage).

[0225] The compositions according to the invention generally exhibit greater... and The mixture provides better grass control.

[0226] Including monounsaturated C 16 -C 22 In the preferred compositions of the invention, fatty acid methyl esters, particularly methyl cis-9-octadecenoate (methyl oleate), component (B) is combined with monounsaturated C 16 -C 22 The weight ratio of fatty acid methyl esters, especially methyl cis-9-octadecenoate (methyl oleate), is preferably in the range of 5:2 to 2:5, more preferably in the range of 2:1 to 1:2, and even more preferably in the range of 7:4 to 3:5.

[0227] In particular, the preferred, more preferred or especially preferred compositions according to the invention have been found to effectively control difficult-to-control weeds, such as alomyces, ryegrass species and brOSS species, which are important weeds in crop plants such as cereals such as wheat, barley or rye.

[0228] Typically, it is found that component (B) is related to monounsaturated C. 16 -C 22 Compositions according to the invention containing fatty acid methyl esters, particularly methyl cis-9-octadecenoate (methyl oleate) in a weight ratio greater than 1:1, can exhibit similar characteristics to component (B) and monounsaturated C in grasses such as alony or ryegrass species. 16 -C 22 Fatty acid methyl esters, particularly methyl cis-9-octadecenoate (methyl oleate), in a weight ratio of 1:1 or less than 1:1, exhibit higher efficacy compared to the compositions according to the invention (see field trial results in the Experimental Section below).

[0229] Therefore, in some embodiments, in the composition according to the invention, component (B) and monounsaturated C 16 -C 22 The weight ratio of fatty acid methyl esters, especially methyl cis-9-octadecenoate (methyl oleate), is preferably greater than 1:1, preferably in the range of 2:1 to 5:4, more preferably in the range of 2:1 to 4:3, and even more preferably in the range of 7:4 to 3:2.

[0230] Other preferred formulation adjuvants (component (H)) in the herbicide concentrate composition according to the invention are selected from isotriadecyl alcohol ethoxylate (6EO) methyl ether, isotriadecyl alcohol ethoxylate (15EO) methyl ether, lithium hydroxyoctadecanoate, quaternary ammonium salt 18-lithium montmorillonite, formic acid and disodium carbonate.

[0231] In a preferred embodiment, the herbicide concentrate composition according to the present invention comprises:

[0232] Component (A), in total amount from 0.5% to 6% by weight.

[0233] Component (B), in total amounts of 10% to 60% by weight.

[0234] C 16 -C 22 C1-C4 alkyl esters of fatty acids, totaling at least 10% by weight.

[0235] Surfactants, in total amount of at least 2% by weight

[0236] And preferably one, two, three or more additional components selected from:

[0237] Other herbicides (component (C)), preferably in a total amount of 0.5% to 12% by weight.

[0238] The safety agent (component (D)) is preferably present in a total amount of 0.75% to 15% by weight.

[0239] Water (component (F)), preferably in a total amount of 0.1% to 30% by weight.

[0240] Other formulation adjuvants (component (H)) are preferably present in a total amount of 0.1% to 50% by weight.

[0241] Based on the total weight of the composition in each case.

[0242] In a preferred embodiment, the herbicide concentrate composition according to the present invention comprises:

[0243] Component (A), in total amount from 0.5% to 6% by weight.

[0244] Component (B), in total amount from 10% to 50% by weight

[0245] C 16 -C 22 Fatty acid methyl esters, totaling at least 10% by weight.

[0246] Surfactants, in total amount of at least 2% by weight

[0247] And preferably one, two, three or more additional components selected from:

[0248] Other herbicides (component (C)), preferably in a total amount of 0.5% to 12% by weight.

[0249] The safety agent (component (D)) is preferably present in a total amount of 0.75% to 15% by weight.

[0250] Water (component (F)), preferably in a total amount of 0.1% to 30% by weight.

[0251] Other formulation adjuvants (component (H)) are preferably present in a total amount of 0.1% to 50% by weight.

[0252] Based on the total weight of the composition in each case.

[0253] In a preferred embodiment, the herbicide concentrate composition according to the present invention comprises:

[0254] Component (A), in total amount from 0.5% to 5% by weight.

[0255] Component (B), in total amount from 10% to 50% by weight

[0256] Monounsaturated C 16 -C 22 Fatty acid methyl esters, in total amounts of 10% to 50% by weight.

[0257] Surfactants, in total amount of at least 3% by weight

[0258] And preferably one, two, three or more additional components selected from:

[0259] Other herbicides (component (C)), preferably in a total amount of 0.5% to 12% by weight.

[0260] The safety agent (component (D)) is preferably present in a total amount of 0.75% to 15% by weight.

[0261] Water (component (F)), preferably in a total amount of 0.1% to 30% by weight.

[0262] Other formulation adjuvants (component (H)) are preferably present in a total amount of 0.1% to 50% by weight.

[0263] Based on the total weight of the composition in each case.

[0264] In a preferred embodiment, the herbicide concentrate composition according to the present invention comprises:

[0265] Component (A), in total amount from 0.5% to 5% by weight.

[0266] Component (B), in total amount from 10% to 50% by weight

[0267] methyl cis-9-octadecenoate (methyl oleate), in a total amount of 10% to 50% by weight.

[0268] Surfactants, in total amount of at least 3% by weight

[0269] And preferably one, two, three or more additional components selected from:

[0270] Other herbicides (component (C)), preferably in a total amount of 0.5% to 12% by weight.

[0271] The safety agent (component (D)) is preferably present in a total amount of 0.75% to 15% by weight.

[0272] Water (component (F)), preferably in a total amount of 0.1% to 30% by weight.

[0273] Other formulation adjuvants (component (H)) are preferably present in a total amount of 0.1% to 50% by weight.

[0274] Based on the total weight of the composition in each case.

[0275] In a preferred embodiment, the herbicide concentrate composition according to the present invention comprises:

[0276] Component (A), in total amount from 0.5% to 5% by weight.

[0277] Component (B), in total amount of 20% to 50% by weight

[0278] methyl cis-9-octadecenoate (methyl oleate), in a total amount of 20% to 50% by weight.

[0279] Surfactants, in total amount of at least 3% by weight

[0280] And one, two, three or more other components selected from:

[0281] Other herbicides (component (C)), preferably in a total amount of 0.5% to 12% by weight.

[0282] The safety agent (component (D)) is preferably present in a total amount of 0.75% to 15% by weight.

[0283] Water (component (F)), preferably in a total amount of 0.1% to 30% by weight.

[0284] Other formulation adjuvants (component (H)) are preferably present in a total amount of 0.1% to 50% by weight.

[0285] Based on the total weight of the composition in each case.

[0286] In a preferred embodiment, the herbicide concentrate composition according to the present invention comprises:

[0287] Component (A), in total amount from 0.5% to 5% by weight.

[0288] Component (B), in total amount of 20% to 50% by weight

[0289] methyl cis-9-octadecenoate (methyl oleate), in a total amount of 20% to 50% by weight.

[0290] Surfactants, in a total amount of at least 3% by weight, preferably selected from castor oil ethoxylates, alkyl sulfosuccinates, and polyethylene glycol mono(tristyrene) ethers.

[0291] And one, two, three or more other components selected from:

[0292] Other herbicides (component (C)), preferably in a total amount of 0.5% to 12% by weight.

[0293] The safety agent (component (D)) is preferably present in a total amount of 0.75% to 15% by weight.

[0294] Water (component (F)), preferably in a total amount of 0.1% to 30% by weight.

[0295] Other formulation adjuvants (component (H)) are preferably present in a total amount of 0.1% to 50% by weight.

[0296] Based on the total weight of the composition in each case.

[0297] In a preferred embodiment, the herbicide concentrate composition according to the present invention comprises:

[0298] Component (A), in total amount from 0.5% to 5% by weight.

[0299] Component (B), in total amount of 20% to 50% by weight

[0300] methyl cis-9-octadecenoate (methyl oleate), in a total amount of 20% to 50% by weight.

[0301] The nonionic surfactant, comprising at least 2% by weight, preferably includes a nonionic surfactant selected from castor oil ethoxylates.

[0302] And one, two, three or more other components, selected from:

[0303] Other herbicides (component (C)), preferably in a total amount of 0.5% to 12% by weight.

[0304] The safety agent (component (D)) is preferably present in a total amount of 0.75% to 15% by weight.

[0305] Water (component (F)), preferably in a total amount of 0.1% to 30% by weight.

[0306] Other formulation adjuvants (component (H)) are preferably present in a total amount of 0.1% to 50% by weight.

[0307] Based on the total weight of the composition in each case.

[0308] In a preferred embodiment, the herbicide concentrate composition according to the present invention comprises:

[0309] Component (A), in total amount from 0.5% to 5% by weight.

[0310] Component (B), in total amount of 20% to 50% by weight

[0311] methyl cis-9-octadecenoate (methyl oleate), in a total amount of 20% to 50% by weight.

[0312] The nonionic surfactant, comprising at least 2% by weight, preferably includes a nonionic surfactant selected from castor oil ethoxylates.

[0313] One or more ionic surfactants, preferably selected from sulfosuccinates,

[0314] And one, two, three or more other components, selected from:

[0315] Other herbicides (component (C)), preferably in a total amount of 0.5% to 12% by weight.

[0316] The safety agent (component (D)) is preferably present in a total amount of 0.75% to 15% by weight.

[0317] Water (component (F)), preferably in a total amount of 0.1% to 30% by weight.

[0318] Other formulation adjuvants (component (H)) are preferably present in a total amount of 0.1% to 50% by weight.

[0319] Based on the total weight of the composition in each case.

[0320] In a preferred embodiment, the herbicide concentrate composition according to the present invention comprises:

[0321] Component (A), in total amount from 0.5% to 4% by weight.

[0322] Component (B), in total amount of 20% to 50% by weight

[0323] methyl cis-9-octadecenoate (methyl oleate), in a total amount of 20% to 50% by weight.

[0324] The nonionic surfactant comprises at least 3% by weight, preferably a nonionic surfactant selected from castor oil ethoxylates.

[0325] One or more ionic surfactants selected from sulfosuccinates, preferably sodium 2-ethylhexylsulfosuccinate.

[0326] And one, two, three or more other components, selected from:

[0327] Other herbicides (component (C)), preferably in a total amount of 0.5% to 12% by weight.

[0328] The safety agent (component (D)) is preferably present in a total amount of 0.75% to 15% by weight.

[0329] Water (component (F)), preferably in a total amount of 0.1% to 30% by weight.

[0330] Other formulation adjuvants (component (H)) are preferably present in a total amount of 0.1% to 50% by weight.

[0331] Based on the total weight of the composition in each case.

[0332] In a preferred embodiment, the herbicide concentrate composition according to the present invention comprises:

[0333] Component (A), in total amount from 0.5% to 4% by weight.

[0334] Component (B), in total amount of 20% to 50% by weight

[0335] methyl cis-9-octadecenoate (methyl oleate), in a total amount of 20% to 50% by weight.

[0336] The weight ratio of component (B) to methyl cis-9-octadecenoate (methyl oleate) is in the range of 2:1 to 1:2.

[0337] The nonionic surfactant comprises or consists of surfactants selected from castor oil ethoxylates, and is at least 3% by weight in total.

[0338] One or more ionic surfactants selected from sulfosuccinates, preferably sodium 2-ethylhexylsulfosuccinate.

[0339] The ratio of the total amount of nonionic surfactant to the total amount of ionic surfactant is preferably in the range of 3:1 to 1:3.

[0340] And one, two, three or more other components, selected from:

[0341] Other herbicides (component (C)), preferably in a total amount of 0.5% to 12% by weight.

[0342] The safety agent (component (D)) is preferably present in a total amount of 0.75% to 15% by weight.

[0343] Water (component (F)), preferably in a total amount of 0.1% to 30% by weight.

[0344] Other formulation adjuvants (component (H)) are preferably present in a total amount of 0.1% to 50% by weight.

[0345] Based on the total weight of the composition in each case.

[0346] In a preferred embodiment, the herbicide concentrate composition according to the present invention comprises:

[0347] Component (A), in total amount from 0.5% to 3% by weight.

[0348] Component (B), in total amount of 20% to 50% by weight

[0349] methyl cis-9-octadecenoate (methyl oleate), in a total amount of 20% to 50% by weight.

[0350] The weight ratio of component (B) to methyl cis-9-octadecenoate (methyl oleate) is in the range of 2:1 to 1:2.

[0351] The nonionic surfactant comprises or consists of surfactants selected from castor oil ethoxylates, and is at least 3% by weight in total.

[0352] One or more ionic surfactants comprising or consisting of sodium 2-ethylhexyl sulfosuccinate, preferably in a total amount of at least 3% by weight.

[0353] The ratio of the total amount of nonionic surfactant to the total amount of ionic surfactant is preferably in the range of 2:1 to 1:2.

[0354] And one, two, three or more other components, selected from:

[0355] Other herbicides (component (C)), preferably in a total amount of 0.5% to 12% by weight.

[0356] The safety agent (component (D)) is preferably present in a total amount of 0.75% to 15% by weight.

[0357] Water (component (F)), preferably in a total amount of 0.1% to 30% by weight.

[0358] Other formulation adjuvants (component (H)) are preferably present in a total amount of 0.1% to 50% by weight.

[0359] Based on the total weight of the composition in each case.

[0360] In all the preferred embodiments described above, the other herbicides (component (C)) and preferred safeners (component (D)) are preferably selected from the corresponding preferred, more preferred or particularly preferred components (C) and components (D) listed above.

[0361] In all the above preferred embodiments, the formulation adjuvant (component (H)) in the herbicide concentrate composition of the present invention is preferably selected from C. 10 -C 22 Fatty alcohol ethoxylated ethers, thickeners and pH adjusters (pH buffers).

[0362] In all the above preferred embodiments, the formulation adjuvant (component (H)) in the herbicide concentrate composition of the present invention is preferably selected from isotrigine tridecyl ethoxylate (6EO) methyl ether, isotrigine tridecyl ethoxylate (15EO) methyl ether, lithium hydroxyoctadecanoate, quaternary ammonium salt 18-lithium montmorillonite, formic acid and disodium carbonate.

[0363] In a more preferred embodiment, the herbicide concentrated composition according to the invention comprises:

[0364] Component (A), in total amount from 0.5% to 2.5% by weight.

[0365] Component (B), in total amount of 20% to 50% by weight

[0366] methyl cis-9-octadecenoate (methyl oleate), in a total amount of 20% to 50% by weight.

[0367] The weight ratio of component (B) to methyl cis-9-octadecenoate (methyl oleate) is in the range of 2:1 to 1:2.

[0368] The nonionic surfactant, comprising at least 2% by weight, preferably includes a nonionic surfactant selected from castor oil ethoxylates.

[0369] The safener (component (D)) is selected from (D1) pyrazole oxalic acid, its esters and / or salts or (D4) oxalic acid, its esters and / or salts, preferably in a total amount of 1% to 10% by weight.

[0370] And one, two, three or more other components, selected from:

[0371] Other herbicides (component (C)), preferably in a total amount of 0.5% to 12% by weight.

[0372] Water (component (F)), preferably in a total amount of 0.1% to 10% by weight.

[0373] Other formulation adjuvants (component (H)) are preferably present in a total amount of 0.1% to 50% by weight.

[0374] Based on the total weight of the composition in each case.

[0375] In a more preferred embodiment, the herbicide concentrated composition according to the invention comprises:

[0376] Component (A), in total amount from 0.5% to 2.5% by weight.

[0377] Component (B), in total amount of 20% to 50% by weight

[0378] methyl cis-9-octadecenoate (methyl oleate), in a total amount of 20% to 50% by weight.

[0379] The weight ratio of component (B) to methyl cis-9-octadecenoate (methyl oleate) is in the range of 2:1 to 1:2.

[0380] The nonionic surfactant comprises at least 3% by weight, preferably a nonionic surfactant selected from castor oil ethoxylates.

[0381] Optionally, an ionic surfactant selected from sulfosuccinates is used, in a total amount of at least 3% by weight.

[0382] Other herbicides (component (C)) selected from (C1) iodosulfuron and its salts, (C2) thiamethoxam and its salts, and mixtures thereof, preferably in a total amount of 0.5% to 8% by weight.

[0383] The safener (component (D)) is selected from (D1) pyrazole oxalic acid, its esters and / or salts or (D4) oxalic acid, its esters and / or salts, preferably in a total amount of 1% to 10% by weight.

[0384] And one, two or more other components, selected from:

[0385] Water (component (F)), preferably in a total amount of 0.1% to 10% by weight.

[0386] Other pharmaceutical adjuvants (component (H)) selected from C 10 -C 22 Fatty alcohol ethoxylated ethers, thickeners, and pH adjusters (pH buffers), preferably in total amounts from 0.1% to 50% by weight.

[0387] Based on the total weight of the composition in each case.

[0388] In a more preferred embodiment, the herbicide concentrated composition according to the invention comprises:

[0389] Component (A), in total amount from 0.5% to 2.5% by weight.

[0390] Component (B), in total amount of 20% to 50% by weight

[0391] methyl cis-9-octadecenoate (methyl oleate), in a total amount of 20% to 50% by weight.

[0392] The weight ratio of component (B) to methyl cis-9-octadecenoate (methyl oleate) is in the range of 2:1 to 1:2.

[0393] The nonionic surfactant comprises at least 3% by weight, preferably a nonionic surfactant selected from castor oil ethoxylates.

[0394] Optionally, an ionic surfactant selected from sulfosuccinates is used, in a total amount of at least 3% by weight.

[0395] Other herbicides (component (C)) are selected from iodosulfuron, iodosulfuron sodium salt, thiamethoxam and mixtures thereof, preferably in a total amount of 0.5% to 8% by weight.

[0396] The safener (component (D)) is selected from pyrazosulfuron or pyrazosulfuron, preferably in a total amount of 1% to 10% by weight.

[0397] And one, two or more other components, selected from:

[0398] Water (component (F)), preferably in a total amount of 0.1% to 10% by weight.

[0399] Other pharmaceutical adjuvants (component (H)) selected from C 10 -C 22 Fatty alcohol ethoxylated ethers, thickeners, and pH adjusters (pH buffers), preferably in total amounts from 0.1% to 50% by weight.

[0400] Based on the total weight of the composition in each case.

[0401] In a more preferred embodiment, the herbicide concentrated composition according to the invention comprises:

[0402] Component (A), in total amount from 0.5% to 2.0% by weight.

[0403] Component (B), in total amount of 20% to 50% by weight

[0404] Methyl cis-9-octadecenoate (methyl oleate), in a total amount of 20% to 50% by weight,

[0405] The weight ratio of component (B) to methyl cis-9-octadecenoate (methyl oleate) is in the range of 2:1 to 1:2.

[0406] The nonionic surfactant comprises at least 3% by weight, preferably a nonionic surfactant selected from castor oil ethoxylates.

[0407] Optionally, an ionic surfactant selected from sulfosuccinates is used, in a total amount of at least 3% by weight.

[0408] Other herbicides (component (C)) are selected from iodosulfuron, iodosulfuron sodium salt, thiamethoxam and mixtures thereof, preferably in a total amount of 0.5% to 8% by weight.

[0409] The safener (component (D)) is selected from (D1) pyrazosulfuron or (D4) pyrazosulfuron, preferably in a total amount of 1% to 10% by weight.

[0410] And one, two or more other components selected from:

[0411] Water (component (F)), preferably in a total amount of 0.1% to 10% by weight.

[0412] Other formulation adjuvants (component (H)) selected from isotriadecyl ethoxylate (6EO) methyl ether, isotriadecyl ethoxylate (15EO) methyl ether, lithium hydroxyoctadecanoate, quaternary ammonium salt 18-lithium montmorillonite, formic acid, and disodium carbonate, preferably in a total amount of 0.1% to 50% by weight.

[0413] Based on the total weight of the composition in each case.

[0414] In a more preferred embodiment, the herbicide concentrated composition according to the invention comprises:

[0415] Component (A), in total amount from 0.5% to 2.0% by weight.

[0416] Component (B), in total amount of 20% to 50% by weight

[0417] methyl cis-9-octadecenoate (methyl oleate), in a total amount of 20% to 50% by weight.

[0418] The weight ratio of component (B) to methyl cis-9-octadecenoate (methyl oleate) is in the range of 7:4 to 3:5, preferably greater than 1:1.

[0419] The nonionic surfactant comprises at least 3% by weight, preferably a nonionic surfactant selected from castor oil ethoxylates.

[0420] Optionally, an ionic surfactant selected from sulfosuccinates is used, in a total amount of at least 3% by weight.

[0421] Other herbicides (component (C)) are selected from iodosulfuron, iodosulfuron sodium salt, thiamethoxam and mixtures thereof, preferably in a total amount of 0.5% to 8% by weight.

[0422] The safener (component (D)) is selected from (D1) pyrazosulfuron or (D4) pyrazosulfuron, preferably in a total amount of 1% to 10% by weight.

[0423] And one, two or more other components, selected from:

[0424] Water (component (F)), preferably in a total amount of 0.1% to 10% by weight.

[0425] Other formulation adjuvants (component (H)) selected from isotriadecyl ethoxylate (6EO) methyl ether, isotriadecyl ethoxylate (15EO) methyl ether, lithium hydroxyoctadecanoate, quaternary ammonium salt 18-lithium montmorillonite, formic acid, and disodium carbonate, preferably in a total amount of 0.1% to 50% by weight.

[0426] Based on the total weight of the composition in each case.

[0427] In all the preferred embodiments and in all the more preferred embodiments described above, in each case, the total amount of component (B) and methyl cis-9-octadecenoate (methyl oleate) present in the herbicide concentrate composition according to the invention is 60% by weight or more, based on the total weight of the composition.

[0428] In addition, fatty alcohol glycol ethers, such as nonionic or ionic fatty alcohol glycol ethers (e.g., fatty alcohol glycol ether sulfate), are known to be suitable as penetrants and synergists for many other herbicides, especially those selected from imidazolinone herbicides; (see, for example, EP-A-0502014).

[0429] The use of vegetable oils can further enhance the herbicidal effect of the herbicide concentrate composition according to the present invention. The term vegetable oil should be understood to mean oil derived from oilseed plant species, such as soybean oil, rapeseed oil, corn oil, sunflower oil, cottonseed oil, linseed oil, coconut oil, palm oil, safflower oil, or castor oil, especially rapeseed oil, and its transesterification products, such as alkyl esters, such as rapeseed oil methyl ester or rapeseed oil ethyl ester.

[0430] The preferred vegetable oil is C. 10 -C 22 -, Preferred C 12 -C 20 -Esters of fatty acids. C 10 -C 22- Fatty acid esters are, for example, unsaturated or saturated C60 esters. 10 -C 22 -Esters of fatty acids, especially those with an even number of carbon atoms, such as erucic acid, lauric acid, palmitic acid, and especially C-esters. 18 - Fatty acids such as stearic acid, oleic acid, linoleic acid, or linolenic acid.

[0431] C 10 -C 22 Examples of fatty acid esters are those made by reacting glycerol or diol with C... 10 -C 22 esters obtained by reacting fatty acids (such as those present in oils from oilseed plant species), or by reacting fatty acids (such as those found in oils from oilseed plant species), or by reacting fatty acids (such as those obtained by reacting fatty acids) with glycerol or glycol. 10 -C 22 - Fatty acid esters and C1-C 20 C1-C obtained by transesterification of an alcohol (e.g., methanol, ethanol, propanol, or butanol). 20 -alkyl-C 10 -C 22 - Fatty acid esters. Transesterification reactions can be carried out by known methods, such as those described in... Chemie Lexikon, 9th edition, Volume 2, page 1343, Thieme Verlag Stuttgart.

[0432] Preferred C1-C 20 -alkyl-C 10 -C 22 - Fatty acid esters are methyl, ethyl, propyl, butyl, 2-ethylhexyl, and dodecyl esters. Preferred are diols and glycerol-C. 10 -C 22 - Fatty acid esters are C 10 -C 22 - Homogeneous or mixed diol esters and glycerides of fatty acids, especially those fatty acids having an even number of carbon atoms, such as erucic acid, lauric acid, palmitic acid, and particularly C. 18 - Fatty acids such as stearic acid, oleic acid, linoleic acid, or linolenic acid.

[0433] In another embodiment, the invention covers a combination of a concentrated herbicide composition comprising components (A), (B), and optionally (C) and / or (D) with the aforementioned vegetable oil, such as rapeseed oil, preferably in the form of a commercially available oil-based formulation additive, particularly those based on rapeseed oil, and especially having rapeseed oil methyl ester as a main ingredient, for example... B(Novance, France), Rako- (Bayer AG, Germany) (Stefes, Germany) or Steefes (Stefes, Germany)

[0434] For use, the herbicide concentrate composition according to the invention is diluted in a conventional manner, for example, with water in the case of wettable powder, emulsifiable concentrate, dispersion and water-dispersible granules.

[0435] In a further aspect, the present invention relates to can-mixed compositions comprising or consisting of the following:

[0436] Component (i) is the herbicide concentrated composition of the present invention.

[0437] Component (ii) Water,

[0438] Optionally, component (iii) includes one or more fatty alcohol glycol ethers and / or one or more vegetable oils or their esters (preferably rapeseed oil methyl ester) and / or one or more alkali metal lauryl ether sulfates (preferably sodium lauryl ether sulfate).

[0439] In each case, based on the total weight of the canned composition, the total weight of component (ii) to the total weight of component (i) is preferably in the range of 50:1 to 800:1, more preferably in the range of 100:1 to 500:1.

[0440] In another aspect, the present invention relates to a method for preparing a can-mixed composition, characterized by the following steps:

[0441] (a) Provides the herbicide concentrate composition described herein as component (i),

[0442] (b) Water as component (ii), wherein the total weight of component (ii) to the total weight of component (i) is preferably in the range of 50:1 to 800:1, more preferably in the range of 100:1 to 500:1.

[0443] (c) Optionally, one or more fatty alcohol glycol ethers and / or one or more vegetable oils or their esters (preferably rapeseed oil methyl ester) and / or one or more alkali metal lauryl ether sulfates (preferably sodium lauryl ether sulfate) are provided as component (iii).

[0444] Components (i) and (ii) and optional component (iii) are mixed in a tank.

[0445] The herbicide concentrate composition or tank-mixed composition according to the invention can be applied to plants, parts of plants, seeds of plants or cultivated areas (soil in the field), preferably to green plants and parts of plants, and, if appropriate, also to the soil in the field.

[0446] The herbicide concentrate compositions according to the invention, having components (A) and (B), have the advantage of being easier to apply because the components are already present in the correct proportions to each other. Furthermore, the adjuvants in such compositions can also be optimally matched to each other. Such herbicide concentrate compositions are referred to in the art as premixes or in-can formulations. These are advantageous compared to adding different components and adjuvants separately to a can to form a spray mixture. The herbicide concentrate compositions according to the invention particularly offer an advantageous activity spectrum and / or high stability (chemical and physical), and are easy to use.

[0447] The compositions described in the context of this invention are suitable for controlling harmful plants (i.e., undesirable plant growth) in plant crops, such as economically important plant crops like cereals (e.g., wheat, barley, rye, oats, rice, corn, millet), sugar beets, sugarcane, rapeseed, cotton, and soybeans. Of particular interest is the application of the compositions described in the context of this invention to monocotyledonous plant crops such as cereals, such as wheat, barley, rye, oats, and especially their hybrids such as triticale, rice, corn, and millet. These plant crops are also preferred for the herbicide concentrate compositions and tank mixtures described in the context of this invention.

[0448] The compositions described in the context of this invention exhibit outstanding herbicidal activity against a broad spectrum of economically important weeds (harmful plants). The active compounds also act effectively on perennial weeds that produce shoots from rhizomes, primary taproots, or other perennial organs and are difficult to control. In this case, it is not important whether the substance is applied before sowing, before emergence, or after emergence. Application after emergence or early application after sowing but before emergence is preferred.

[0449] Specifically, some representative examples of monocotyledonous and dicotyledonous weed communities that can be controlled by the compositions according to the invention may be mentioned, but the list is not limited to specific species.

[0450] Examples of weed species for which the compositions are effective as described in the context of this invention are derived from monocotyledonous weed species, such as those from the annual group: *Apera* (e.g., *Apera spica venti*), *Avena* (e.g., wild oats), *Alopecurus* (e.g., large-spike wild oats), *Brachiaria*, *Digitaria*, *Lolium* (e.g., multiflora ryegrass and rigid ryegrass), *Echinochloa*, *Panicum*, *Phalaris* (e.g., *Phalaris arundinacea* and canary grasses). Grasses (Phalariscanariensis), Poa species such as Poa annum, Setaria species such as Setaria pumila and Setaria viridis, Bromus species such as Bromus catharticus, Bromus secalinus, Bromus erectus, Bromus tectorum and Bromus japonicus, Cyperus species, and perennial species including Agropyron, Cynodon, Imperata and Sorghum, as well as perennial Cyperus species.

[0451] In the case of dicotyledonous weed species, the spectrum of action extends to species, such as in annuals, including genera such as *Abutilon*, *Amaranthus*, *Chenopodium*, *Chrysanthemum*, *Galium* (e.g., *Galium aparine*), *Geranium* (e.g., *Geranium dissectum*), *Ipomoea*, *Kochia*, *Lamium*, *Matricaria* (e.g., *Matricaria chamomilla*), *Papaver* (e.g., *Papaver rhoeas*), *Pharbitis*, and *Polygonum* (e.g., *Polygonum*). The genera include *Convolvulus*, *Sida*, *Sinapis*, *Solanum*, *Stellaria*, *Veronica* (such as *Veronica hederifolia*), *Viola* (such as *Viola arvensis* and *Viola tricolor*), *Xanthium*, and among perennial weeds, *Convolvulus*, *Cirsium*, *Rumex*, and *Artemisia*.

[0452] In the context of this invention, harmful plants (weed species) are preferably selected from the genera *Alopecurus* (especially *Alopecurus myosuroides*), *Apera* (especially *Apera spica-venti*), *Avena* (especially *Avena fatua*), *Brachiaria*, *Bromus* (especially *Bromus catharticus*, *Bromus secalinus*, *Bromus erectus*, *Bromus tectorum*, and *Bromus japonicus*), *Echinochloa*, *Galium* (especially *Galium cleavers*), *Geranium* (especially *Geranium dissectum*), and *Lolium* (especially *Lolium multiflorum*). multiflorum and rigid ryegrass (Lolium rigidum), Matricaria (especially Matricaria chamomilla), Papaver (especially Papaver rhoeas), Phalaris (especially Phalaris arundinacea and canary) Phalaenopsis canariensis), Poa (especially Poa annum), Polygonum (especially Polygonum convolvulus), Setaria (especially Setaria pumila and Setaria viridis), Veronica (especially Veronica hederifolia) and Viola (especially Viola arvensis and Viola tricolor)

[0453] Therefore, in another aspect, the present invention relates to a method for controlling harmful plants, comprising applying a concentrated herbicide composition or canned composition as defined herein to a plant, plant part, plant seed or area of ​​plant growth, preferably for selectively controlling harmful plants in a plant crop.

[0454] Furthermore, the present invention relates to the use of herbicide concentrated compositions or canned compositions as defined herein for the control of harmful plants.

[0455] In particular, the present invention relates to methods and uses for controlling harmful plants, wherein the harmful plants are preferably selected from the genera *Alopecurus* (especially *Alopecurus myosuroides*), *Apera* (especially *Apera spica-venti*), *Avena* (especially *Avenafatua*), *Bromus* (especially *Bromus catharticus*, *Bromus secalinus*, *Bromus erectus*, *Bromus tectorum*, and *Bromus japonicus*), *Galium* (especially *Galium aparine*), *Lolium* (especially *Lolium multiflorum* and *Lolium rigidum*), and *Matricaria* (especially *Matricaria*). chamomilla), poppy (especially Papaver rhoeas), pheasant (especially Phalaris arundinacea and canary), and pheasant (especially Phalaris arundinacea and canary). Phalaenopsis canariensis), Poa (especially Poa annum), Polygonum (especially Polygonum convolvulus), Setaria (especially Setaria pumila and Setaria viridis), Veronica (especially Veronica hederifolia) and Viola (especially Viola arvensis and Viola tricolor)

[0456] If the composition described in the context of this invention is applied to the soil surface before germination, weed seedlings are either completely prevented from germinating, or the weeds grow until they reach the cotyledon stage, but then their growth stops and they eventually die completely after three to four weeks.

[0457] If the components of the composition described in the context of this invention are applied to the green parts of the plant after emergence, growth also stops dramatically within a very short time after treatment, and the weeds remain in the growth stage at the time of application, or die completely after a certain period of time, thereby eliminating competition from harmful weeds for the crop plant in a continuous manner at a very early time.

[0458] The compositions described in the context of this invention are characterized by rapid onset and sustained weed control. Generally, the rainfastness of the active compounds in the compositions of this invention is advantageous. A particular advantage is that the dosage of the herbicidal active ingredient present in the compositions described in the context of this invention can be adjusted to such low levels that its soil action is optimally low. This not only allows for initial application to sensitive crops but also effectively avoids groundwater and surface water contamination. The compositions described in the context of this invention allow for a significant reduction in the required amount of herbicidal active compound to be applied.

[0459] The beneficial effects of the compositions described in the context of this invention can allow for reduced application rates, broader spectrum of weed control, faster herbicidal action, longer duration of action, and / or better control of harmful plants, while using less application.

[0460] From both a qualitative and quantitative perspective, the aforementioned properties and advantages are beneficial for weed control practices to keep crops free from unwanted competing plants and thus protect and / or increase yields. Example

[0461] Unless otherwise stated, all quantities and percentages refer to weight.

[0462] The following substances and abbreviations are used in the following embodiments:

[0463]

[0464]

[0465] A. Formulation Examples

[0466] Table A1-1: OD formulations with MSS and MPR

[0467] g / L g / L g / L MSS 15.7 15.7 9.4 MPR 45.0 30.0 27.0 EMULSOGEN EL 400 55.8 56.4 55.8 Formic acid 0.01 2.1 0.01 Sodium carbonate 0.01 0.01 0.01 LIGASTAR LI 12OXY 0.0 28.2 0.0 BENTONE 38 18.6 2.8 23.3 propylene carbonate 1.9 0.3 1.9 TEHP 372.0 376.0 372.0 TRITON GR 7ME 46.5 47.0 46.5 Radia 7066 374.5 381.5 394.0

[0468] Table A1-2: OD formulations with MSS and MPR

[0469]

[0470] Table A2-1: OD formulations with IMS, MSS, TCM and MPR

[0471] g / L g / L g / L IMS 3.0 3.0 3.0 MSS 15.7 15.7 15.7 TCM 7.5 7.5 7.5 MPR 45.0 45.0 45.0 EMULSOGEN EL 400 57.0 57.0 57.0 Formic acid 1.0 1.0 1.0 Sodium carbonate 0.01 0.01 0.01 GENAPOL XM 060 0.0 0.0 142.5 LIGASTAR LI 12OXY 28.5 28.5 28.5 BENTONE 38 4.8 4.8 4.8 propylene carbonate 2.9 2.9 2.9 TEHP 285.0 475.0 142.5 TRITON GR 7ME 47.5 47.5 47.5 Radia 7066 452.2 262.2 452.2

[0472] Table A2-2: OD formulations with IMS, MSS, TCM and MPR

[0473]

[0474]

[0475] Table A2-3: OD formulations with IMS, MSS, TCM and MPR

[0476] g / L g / L g / L IMS 3.0 3.0 3.0 MSS 15.7 15.7 15.7 TCM 5.0 5.0 5.0 MPR 45.0 45.0 45.0 EMULSOGEN EL 400 57.0 57.0 0.0 ETOCAS 10 0.0 0.0 47.5 Formic acid 1.0 1.0 1.0 Sodium carbonate 0.01 0.01 0.01 GENAPOL XM 060 0.0 237.5 190.0 LIGASTAR LI 12OXY 28.5 28.5 28.5 BENTONE 38 2.9 2.9 2.85 propylene carbonate 2.9 2.9 0.285 TEHP 475.0 237.5 380.0 TRITON GR 7ME 47.5 47.5 47.5 Radia 7066 266.6 267.6 184.6

[0477] Table A2-4: OD formulations with IMS, MSS, TCM and MPR

[0478]

[0479]

[0480] Table A2-5: OD formulations with IMS, MSS, TCM and MPR

[0481] g / L g / L IMS 3.0 3.0 MSS 12.5 12.5 TCM 5.0 5.0 MPR 45.0 45.0 EMULSOGEN EL 400 57.0 47.5 Formic acid 1.0 1.0 Sodium carbonate 0.01 0.01 GENAPOL XM 060 0.0 190.0 LIGASTAR LI 12OXY 28.5 28.5 BENTONE 38 2.9 2.9 propylene carbonate 2.9 2.9 TEHP 475.0 380.0 TRITON GR 7ME 47.5 47.5 Radia 7066 270.4 187.8

[0482] Table A2-6: OD formulations with IMS, MSS, TCM and MPR

[0483]

[0484]

[0485] Table A2-7: OD formulations with IMS, MSS, TCM and MPR

[0486]

[0487] Table A3-1: OD formulations containing MSS, TCM and MPR

[0488]

[0489]

[0490] Table A3-2: OD formulations containing MSS, TCM and MPR

[0491] g / L g / L g / L MSS 15.7 15.7 15.7 TCM 5.0 5.0 5.0 MPR 37.5 37.5 37.5 EMULSOGEN EL 400 46.5 0.0 57.0 ETOCAS 10 0.0 47.5 0.0 Formic acid 0.01 0.01 2.1 Sodium carbonate 0.01 0.01 0.01 GENAPOL XM 060 186.0 0.0 190.0 GENAPOL XM 150 0.0 142.5 0.0 LIGASTAR LI 12OXY 27.9 28.5 28.5 BENTONE 38 2.8 0.0 2.9 propylene carbonate 0.3 0.0 0.3 TEHP 372.0 285.0 380.0 TRITON GR 7ME 46.5 47.5 47.5 Radia 7066 189.8 340.8 183.6

[0492] Table A3-3: OD formulations containing MSS, TCM, and MPR

[0493]

[0494]

[0495] Table A3-4: OD formulations containing MSS, TCM, and MPR

[0496] g / L g / L MSS 12.5 12.5 TCM 5.0 5.0 MPR 37.5 37.5 EMULSOGEN EL 400 55.8 46.5 Formic acid 0.01 0.01 Sodium carbonate 0.01 0.01 GENAPOL XM 060 0.0 186.0 LIGASTAR LI 12OXY 27.9 27.9 BENTONE 38 2.8 2.8 propylene carbonate 0.3 0.3 TEHP 465.0 372.0 TRITON GR 7ME 46.5 46.5 Radia 7066 276.7 193.0

[0497] Table A3-5: OD formulations containing MSS, TCM, and MPR

[0498]

[0499]

[0500] Table A3-6: OD formulations containing MSS, TCM, and MPR

[0501] g / L g / L g / L MSS 9.4 9.4 9.4 TCM 5.0 5.0 5.0 MPR 37.5 37.5 37.5 EMULSOGEN EL 400 57.0 56.4 56.4 Formic acid 2.1 2.1 2.1 Sodium carbonate 0.01 0.01 0.01 LIGASTAR LI 12OXY 28.5 28.2 28.2 BENTONE 38 2.9 2.8 2.8 propylene carbonate 0.3 0.3 0.3 TEHP 475.0 470.0 376.0 TRITON GR 7ME 47.5 47.0 47.0 Radia 7066 284.9 281.3 375.3

[0502] Table A3-7: OD formulations containing MSS, TCM, and MPR

[0503]

[0504]

[0505] Table A3-8: OD formulations containing MSS, TCM, and MPR

[0506] g / L g / L g / L MSS 6.3 6.3 6.3 TCM 5.0 5.0 5.0 MPR 37.5 37.5 37.5 EMULSOGEN EL 400 56.4 57.0 56.4 Formic acid 2.1 2.1 2.1 Sodium carbonate 0.01 0.01 0.01 GENAPOL XM 060 0.0 190 0.0 LIGASTAR LI 12OXY 28.2 28.5 28.2 BENTONE 38 2.8 2.9 2.8 propylene carbonate 0.3 0.3 0.3 TEHP 470.0 380.0 376.0 TRITON GR 7ME 47.0 47.5 47.0 Radia 7066 284.4 193.0 378.4

[0507] Table A3-9: OD formulations containing MSS, TCM, and MPR

[0508]

[0509]

[0510] B. Biological Examples

[0511] Greenhouse Experiment (Not based on this invention)

[0512] The percentage damage (damage) shown refers to the maximum damage observed in each crop.

[0513] Table G1: Greenhouse Selectivity Trials Using MSM, IMS, and MPR – Post-emergence Wheat Crop Damage When Appropriate Substances Were Applied at Plant Heights of Approximately 35 cm (TRZAW, Winter Wheat) or Approximately 40 cm (TRZDU, Durum Wheat)

[0514]

[0515] *: G-TEHP: 80% TEHP, 10% LRO paste and 10% CO

[0516] LRO paste is C 12 -C 14 Fatty alcohol diethylene glycol ether sulfate, sodium salt, 70% aqueous solution, commercially available.

[0517] CO is castor oil ethoxylate (a nonionic emulsifier), commercially available.

[0518] #: TBEP: Tris(butoxyethyl) phosphate, commercially available

[0519] Field / Outdoor Trials

[0520] After the harmful plants emerge, usually at the 2- to 4-leaf stage, treat them with the appropriate substance shown at a water application rate of 100 to 400 l / ha.

[0521] Following treatment (usually 3-6 weeks after application, depending on environmental conditions), the herbicidal activity of the corresponding substances was visually scored by comparing treated plots with untreated control plots. Damage and development on all aboveground parts of the plants were recorded. Scoring was based on a percentage scale (100% effect = all plants died; 50% effect = 50% of plants and green parts died; 0% effect = no identifiable effect = similar to the control plot). In each case, the scores of 3, 6, or 8 plots were averaged across different locations in six different European countries during the spring.

[0522] In each case, the dosage rate of the herbicidal ingredient used is specified for the corresponding active ingredient and refers to the amount of active ingredient per hectare (g / hectare).

[0523] The observed herbicidal effects of herbicides are expressed as % activity against the corresponding weeds. The % damage (damage) shown refers to the maximum damage observed in winter wheat (TRZAW) crop.

[0524] Table Ref-F1 (not based on this invention): Field selective trials using MSM and MPR - Post-emergence winter wheat (TRZAW) crop damage (injury)

[0525]

[0526] MERO: Rapeseed Oil Methyl Ester

[0527] *:G-TEHP: 80% TEHP, 10% LRO paste and 10% CO 30

[0528] LRO paste is C 12 -C 14 Fatty alcohol diethylene glycol ether sulfate, sodium salt, 70% aqueous solution, commercially available.

[0529] CO is castor oil ethoxylate (a nonionic emulsifier), commercially available.

[0530] Field trials of herbicidal activity:

[0531] The weeds being tested:

[0532] ALOMY: Large-eared wheatgrass (Alopecurus myosuroides)

[0533] LOLSS: Ryegrass (Lolium sp.)

[0534] BROSS: Bromos sp.

[0535] Table F1: Field weed control trials using MSM and MPR

[0536]

[0537] (Commercially available herbicides): Mesosulfuron-methyl + Pyrazosulfuron-methyl WG 13.5 (4.5 + 9 g / kg)

[0538] *: Sodium lauryl ether sulfate, commercially available

[0539] Sigma (Commercially available herbicides): Mesosulfuron-methyl + Pyrazosulfuron-methyl OD 120 (30 + 90 g / L)

[0540] Table F2-1: Field weed control trials with MSM, TCM and MPR

[0541]

[0542]

[0543] (Commercially available herbicides): Mesosulfuron-methyl + Thiamethoxam + Pyrazosulfuron-methyl WG (45+15+112.5g / kg)

[0544] *: Sodium lauryl ether sulfate, commercially available

[0545] Table F2-2: Field weed control trials with MSM, TCM and MPR

[0546]

[0547]

[0548] (Commercially available herbicides): Mesosulfuron-methyl + Thiamethoxam + Pyrazosulfuron-methyl WG (45+15+112.5g / kg)

[0549] *: Sodium lauryl ether sulfate, commercially available

[0550] The compositions according to the invention tested in the field generally show better performance than... and The mixture provides better weed control.

[0551] In addition, compared with commercially available herbicides (Mesosulfuron-methyl + Thiamethoxam + Pyrazosulfuron-methyl WG (45+15+112.5g / kg) and Compared to combinations containing sodium lauryl ether sulfate, the compositions according to the invention, as tested in the field, showed similar crop safety (crop damage) in winter wheat (TRZAW) after emergence.

Claims

1. A composition comprising an effective amount of component (A), wherein (A) represents mesosulfuron-methyl and / or its salts. (B) indicates tris(2-ethylhexyl) phosphate (TEHP). And optionally one or more other compounds selected from components (C) and (D): (C) One or more additional herbicides selected from the following: (C1) Iodosulfuron and its salts, (C2) Thiazolylsulfuron and its salts, (C3) Acrylsulfuron and its salts, (C4) Formamidesulfuron and its salts, (C5) Probenzylsulfuron and its salts, and (C6) Pyrfluthrin. (D) One or more safety agents, Wherein, based on the total weight of the composition, the weight ratio of the total amount of component (A) to the total amount of component (B) is in the range of 1:2 to 1:100, and wherein the composition comprises The total amount of methyl cis-9-octadecenoate (methyl oleate) is 10% to 50% by weight. The composition therein does not contain zopyrrolizidine ester.

2. The composition according to claim 1, wherein the composition is free of C1-C6 alkyl methacrylates.

3. The composition according to claim 1, wherein components (A) and (C) are the only herbicides in the composition.

4. The composition according to claim 1, wherein in each case, based on the total weight of the composition, the weight ratio of the total amount of component (A) to the total amount of component (B) is in the range of 1:3 to 1:

100.

5. The composition according to claim 1, wherein in each case, based on the total weight of the composition, the weight ratio of the total amount of component (A) to the total amount of component (B) is in the range of 1:4 to 1:

100.

6. The composition according to claim 1, wherein in each case, based on the total weight of the composition, the weight ratio of the total amount of component (A) to the total amount of component (B) is in the range of 1:4 to 1:

80.

7. The composition according to claim 1, wherein in each case, based on the total weight of the composition, the weight ratio of the total amount of component (A) to the total amount of component (B) is in the range of 1:4 to 1:

60.

8. The composition according to claim 1, wherein in each case, based on the total weight of the composition, the weight ratio of the total amount of component (A) to the total amount of component (B) is in the range of 1:4 to 1:

50.

9. The composition according to claim 1, wherein in each case, based on the total weight of the composition, the weight ratio of the total amount of component (A) to the total amount of component (B) is in the range of 1:4 to 1:

40.

10. The composition according to claim 1, wherein in each case, based on the total weight of the composition, the weight ratio of the total amount of component (A) to the total amount of component (B) is in the range of 1:5 to 1:

30.

11. The composition according to claim 1, wherein in each case, the component (B) is present in a total amount of 10% to 50% by weight, based on the total weight of the composition.

12. The composition according to claim 1, wherein in each case, the component (B) is present in a total amount of 15% to 45% by weight based on the total weight of the composition.

13. The composition according to claim 1, wherein in each case, the component (B) is present in a total amount of 20% to 40% by weight, based on the total weight of the composition.

14. The composition according to claim 1, wherein the safener of component (D) is selected from: (D1) pyrazole oxalic acid, its ester and / or its salt, (D2) bis(oxazolyl) acid, its ester and / or its salt, (D3) cyclopropanesulfonamide, its ester and / or its salt, (D4) oxalic acid, its ester and / or its salt, (D5) oxazolyl sulfadiazine, its ester and / or its salt, and (D6) oxazolyl sulfadiazine, its ester and / or its salt.

15. The composition according to claim 14, wherein the safener of component (D) is selected from: pyrazolium oxychloride, ethyl bis(oxazolyl) oxychloride, cyclopropanesulfonamide, pyrazolium oxychloride, pyrazolium oxychloride, and pyrazolium oxychloride.

16. The composition according to claim 1, further comprising one or more additional components selected from other formulation adjuvants and additives commonly used in crop protection, selected from components (E) to (G): (E) Surfactants, (F) Water, (G) Organic solvents.

17. The composition according to claim 1, comprising... Component (A) in total amounts of 0.5% to 6% by weight, Component (B) in total amounts of 10% to 50% by weight, And one, two, three or more other components selected from components (C) to (H): Other herbicides (component (C)) in total amounts of 0.5% to 12% by weight, The total amount of safety agent (component D) is 0.75% to 15% by weight. The total amount of surfactant (component (E)) ranges from 0.1% to 60% by weight. Water (component (F)) in total amounts ranging from 0.1% to 30% by weight. Organic solvents (component (G)) in total amounts ranging from 0.1% to 20% by weight. Other formulation adjuvants (component (H)) in total amounts ranging from 0.1% to 50% by weight. In each case, the total weight of the composition shall be considered.

18. The composition according to claim 17, wherein the total amount of said component (A) is from 1% to 5% by weight.

19. The composition according to claim 17, wherein the total amount of said component (B) is from 15% to 45% by weight.

20. A canned composition comprising or consisting of the following: Component (i) is the composition according to one or more of claims 1 to 19. Component (ii) Water, In each case, based on the total weight of the canned composition, the total weight of component (ii) to the total weight of component (i) is in the range of 50:1 to 800:

1.

21. A can-mixed composition comprising or consisting of the following: Component (i) is the composition according to one or more of claims 1 to 19. Component (ii) Water, And component (iii) one or more fatty alcohol glycol ethers and / or one or more vegetable oils or their esters and / or one or more alkali metal lauryl ether sulfates, In each case, based on the total weight of the canned composition, the total weight of component (ii) to the total weight of component (i) is in the range of 50:1 to 800:

1.

22. A method for controlling harmful plants, comprising applying a composition according to one or more of claims 1 to 19 or a tank-mixed composition according to claim 20 or 21 to the plant, a portion of the plant, the seed of the plant or an area where the plant grows, wherein the amount of component (A) applied is in the range of 0.5 to 50 g / ha.

23. Use of the composition according to any one of claims 1 to 19 or the tank-mixed composition according to claim 20 or 21 for controlling harmful plants, wherein the application amount of component (A) is in the range of 0.5 to 50 g / ha.

24. The method according to claim 22 or the use according to claim 23, wherein the harmful plant is selected from the genera *Alopecurus*, *Alopecurus*, *Oat*, *Alopecurus*, *Broomgrass*, *Barnyardgrass*, *Gnaphalium*, *Geranium*, *Lolium*, *Matricaria*, *Papaver*, *Gnaphalium*, *Poa*, *Polygonum*, *Setaria*, *Veronica*, and *Viola*.

25. A method for preparing a can-mixed composition, characterized by the following steps: (a) Providing the composition according to any one of claims 1 to 19 as component (i), (b) Water is provided as component (ii), wherein the total weight of component (ii) is in the range of 50:1 to 800:1 relative to the total weight of component (i). Components (i) and (ii) are mixed in a tank.

26. A method for preparing a can-mixed composition, characterized by the following steps: (a) Providing the composition according to any one of claims 1 to 19 as component (i), (b) Water is provided as component (ii), wherein the total weight of component (ii) is in the range of 50:1 to 800:1 relative to the total weight of component (i). (c) Provide one or more fatty alcohol glycol ethers and / or various vegetable oils or their esters and / or one or more alkali metal lauryl ether sulfates as components (iii). Components (i) and (ii) and component (iii) are mixed in a tank.

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