Compositions Comprising Ethofumesate and a Safener

Abstract

The present invention mainly relates to the (use of) a specific herbicidal composition comprising (i) ethofumesate according to formula (I) and (ii) a safener in the protection of crop plants, in particular cereals such as wheat or barley. The invention also relates to the use of said composition in the agricultural field and for controlling harmful plants. The invention further relates to a corresponding method.

Description

[Technical field]

[0001] The present invention mainly relates to the (use of) certain herbicidal compositions comprising (i) ethofumesate according to formula (I) and (ii) a safener (in the protection of crop plants, in particular cereals such as wheat or barley). The invention also relates to the use of said compositions in the agricultural field and for controlling harmful plants. The invention further relates to the corresponding methods. [Background technology]

[0002] Ethofumesate of formula (I) below (IUPAC name 2-ethoxy-2,3-dihydro-3,3-dimethylbenzofuran-5-yl methanesulfonate) is a known benzofuran herbicide. It is used pre- and post-emergence for grass and broadleaf weed control in a variety of crops, particularly sugar beet.

[0003] [ka]

[0004] EP 0 113 169 A2 teaches herbicidal mixtures with synergistic activity based on the combination of (a) quizalafop, or a salt or ester thereof, and (b) benazolin, or a salt or ester thereof, and / or ethofumesate.

[0005] WO2008 / 075065A2 relates to the protection of wheat crops by using a composition comprising ethofumesate as herbicide, wherein said composition is applied to the wheat crop either pre-emergence or post-emergence, in particular not before ZCK 13, and said composition is applied to the wheat such that an amount of ethofumesate between about 50 g / ha and about 800 g / ha is applied.

[0006] WO2020 / 078874A1 discloses herbicide combinations based on a combination of ethofumesate and bixlozone, optionally including safeners or further herbicides.

[0007] Weed Science, 1975, Vol. 23, 409-413, inter alia, observed that at rates of 2.2 to 9.0 kg / ha, maize yields were reduced in proportion to the rate of ethofumesate applied three weeks before planting, and in greenhouse studies, barley and wheat were approximately 10 times more sensitive to soil residues of ethofumesate than maize.

[0008] Weed Science, 1977, Vol. 25, 252-255 reported that ethofumesate applied pre- or early post-emergence at 0.8-4.5 kg / ha in Italian ryegrass (Lolium multiflorum Lam.) seed fields eliminated annual bluegrass (Poa annua L.).

[0009] Weed Science,1980,Vol.28,292-294 evaluated in field trials the control of volunteer wheat (Triticum aestivum L.) in autumn-planted perennial ryegrass (Lolium perenne L.) at rates of 0.6-4.5 kg / ha. Ethofumesate applied at 1.7 kg / ha or greater to wheat at the 1-3 leaf stage eliminated wheat. Wheat was not excluded when ethofumesate was applied prior to emergence immediately after planting or at the end of November to wheat at the 4 leaf-4 tiller stage.

[0010] Weed Science, 1981, Vol. 29, 712-717, reports on the effect of pre-irrigation duration on the pre-emergence activity of ethofumesate applied to dry soil, followed by irrigation and stand establishment of either sweet corn or winter wheat. [Prior art documents] [Patent documents]

[0011] [Patent Document 1] European Patent Application Publication No. 0113169 [Patent Document 2] International Publication No. 2008 / 075065 [Patent Document 3] International Publication No. 2020 / 078874 [Non-patent literature]

[0012] [Non-Patent Document 1] Weed Science,1975,Vol.23,409-413 [Non-Patent Document 2] Weed Science,1977,Vol.25,252-255 [Non-Patent Document 3] Weed Science,1980,Vol.28,292-294 [Non-Patent Document 4] Weed Science,1981,Vol.29,712-717 Summary of the Invention [Problem to be solved by the invention]

[0013] The herbicidal crop protection agents (herbicides) and compositions thereof known so far for controlling harmful plants or undesirable vegetation have some drawbacks, in particular: (a) they have no herbicidal activity or have insufficient herbicidal activity against certain harmful plants, (b) the range of harmful plants that can be controlled by herbicides is not wide enough, (c) the selectivity of herbicides in crops and their compatibility with crops are too low, causing undesirable damage to crops and / or undesirable reduction in harvest yield, (d) their initial herbicidal activity is unacceptable or not strong enough, and / or (e) their herbicidal activity does not last long enough.Therefore, there is a constant need to develop new herbicidal compositions that have advantages over known ones, at least in some areas.

[0014] Surprisingly, it has now been found that certain compositions comprising ethofumesate exhibit improved crop compatibility, i.e., reduced crop damage, particularly in cereal crops such as wheat or barley, and in particular in cereal crops such as winter wheat and winter barley.

[0015] The present invention is primarily based on the observation that safeners are capable of reducing crop damage caused by ethofumesate in crop plants (crops), i.e. desired plants, in particular monocotyledonous crop plants such as cereals, in particular in early post-emergence stages of growth of crop plants before BBCH13, in particular in wheat crop plants and barley crop plants, in particular winter wheat crop plants and winter barley crop plants.

[0016] The use of safeners to reduce crop damage that can be caused by ethofumesate to crop plants has not previously been reported and is surprising given that safeners typically exhibit their safening effect only against and in combination with specific herbicides or sometimes only against structurally similar herbicide classes.

[0017] For example, the safener mefenpyr-diethyl is effective in safening ALS inhibitors such as mesosulfuron and iodosulfuron, as well as their esters and salts.

[0018] The Weed Science Society of America (WSSA) has published a "Herbicide Site of Action (SOA) Classification List" in which various herbicides are grouped according to their site of action. These WSSA groups are known to those skilled in the art. Herbicides from WSSA Group 15 are very long chain fatty acid (VLCFA) synthesis inhibitor herbicides.

[0019] However, ethofumesate is not an ALS inhibitor, does not share structural similarity with ALS inhibitors, and does belong to WSSA Group 15. In independent experiments, the safener mefenpyr-diethyl was found to have no safener effect when used with flufenacet, an herbicide that also belongs to WSSA Group 15 (e.g., in cereal crops such as wheat or barley).

[0020] Moreover, it has been found that the composition (used) according to the invention provides the weed control activity of ethofumesate with respect to harmful plants (weeds) and at the same time does not (substantially) damage crop plants.The composition (used) according to the invention therefore allows the control of harmful plants that can be controlled by ethofumesate and achieves improved safety in use for crop plants. [Means for solving the problem]

[0021] Thus, in a first aspect, the present invention provides a method for producing a method for treating a cancer cell comprising the steps of: (i) Ethofumesate of formula (I)

[0022] [ka] and (ii) one or more safeners wherein components (i) and (ii) are present in a ratio within the range of 6:1 to 1:4, based on the total weight of the composition, and component (i) is the only herbicidally active ingredient.

[0023] Preferably, components (i) and (ii) are the only pesticidally active compounds present in the composition.

[0024] The compositions of the invention are particularly suitable for the protection of cereal crop plants, such as wheat and barley crop plants, in particular winter wheat and winter barley crop plants. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0025] Definition of ingredient (ii), safener

[0026] Useful combination partners of the compounds of general formula (I) according to the invention also include, for example, the following safeners:

[0027] S1) Compounds from the group of heterocyclic carboxylic acid derivatives:

[0028] S1 a ) Compounds of the type dichlorophenylpyrazoline-3-carboxylic acid (S1 a ), preferably compounds such as: 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylic acid, ethyl 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate (S1-1) ("mefenpyr(-diethyl)") and related compounds (which are described in WO-A-91 / 07874);

[0029] S1 b ) Derivatives of dichlorophenylpyrazole carboxylic acid (S1 b ), preferably compounds such as: 1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate ethyl (S1-2), 1-(2,4-dichlorophenyl)-5-isopropylpyrazole-3-carboxylate ethyl (S1-3), Ethyl 1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)pyrazole-3-carboxylate (S1-4) and related compounds (which are described in EP-A-333 131 and EP-A-269 806);

[0030] S1 c ) Derivatives of 1,5-diphenylpyrazole-3-carboxylic acid (S1 c ), preferably compounds such as: 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate ethyl (S1-5), Methyl 1-(2-chlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-6) and related compounds (which are described, for example, in EP-A-268554);

[0031] S1 d ) Triazole carboxylic acid type compounds (S1 d ), preferably compounds such as: Fenchlorazole(-ethyl), i.e. ethyl 1-(2,4-dichlorophenyl)-5-trichloromethyl-(1H)-1,2,4-triazole-3-carboxylate (S1-7) and related compounds (which are described in EP-A-174 562 and EP-A-346 620);

[0032] S1 e ) Compounds of the type 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (S1 e), preferably compounds such as ethyl 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylate (S1-8) or ethyl 5-phenyl-2-isoxazoline-3-carboxylate (S1-9) and related compounds, which are described in WO-A-91 / 08202, or 5,5-diphenyl-2-isoxazolinecarboxylic acid (S1-10) or ethyl 5,5-diphenyl-2-isoxazolinecarboxylate (S1-11) ("isoxadifen-ethyl") or n-propyl 5,5-diphenyl-2-isoxazolinecarboxylate (S1-12) or ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (S1-13), which are described in patent application WO-A-95 / 07897.

[0033] S2) Compounds of 8-quinolinoxy derivatives (S2):

[0034] S2 a ) 8-Quinolineoxyacetic acid type compounds (S2 a ), preferably 1-methylhexyl (5-chloro-8-quinolinoxy)acetate (generic name "cloquintocet-mexyl") (S2-1), 1,3-dimethylbut-1-yl (5-chloro-8-quinolinoxy)acetate (S2-2), (5-chloro-8-quinolinoxy)acetic acid 4-allyloxybutyl (S2-3), (5-chloro-8-quinolinoxy)acetic acid 1-allyloxyprop-2-yl (S2-4), (5-chloro-8-quinolinoxy)ethyl acetate (S2-5), (5-chloro-8-quinolinoxy)methyl acetate (S2-6), (5-chloro-8-quinolinoxy)allyl acetate (S2-7), (5-chloro-8-quinolinoxy)acetic acid 2-(2-propylideneiminooxy)-1-ethyl (S2-8), 2-oxo-prop-1-yl (5-chloro-8-quinolinoxy)acetic acid (S2-9) and related compounds, which are described in EP-A-86 750, EP-A-94 349 and EP-A-191 736 or EP-A-0 492 366, and also (5-chloro-8-quinolinoxy)acetic acid (S2-10), its hydrates and salts, for example its lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts, which are described in WO-A-2002 / 34048;

[0035] S2 b ) (5-chloro-8-quinolinoxy)malonic acid type compounds (S2 b ), preferably compounds such as diethyl (5-chloro-8-quinolinoxy)malonate, diallyl (5-chloro-8-quinolinoxy)malonate, methylethyl (5-chloro-8-quinolinoxy)malonate and related compounds, which are described in EP-A-0 582 198.

[0036] S3) Active compounds (S3) of the dichloroacetamide type, which are often used as pre-emergence safeners (soil-acting safeners), e.g. "Dichlormid" (N,N-diallyl-2,2-dichloroacetamide) (S3-1), "R-29148" (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) (S3-2), "R-28725" (3-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine) (S3-3), "Benoxacor" (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4), "PPG-1292" (N-allyl-N-[(1,3-dioxolan-2-yl)methyl]dichloroacetamide) (S3-5), "DKA-24" (N-allyl-N-[(allylaminocarbonyl)methyl]dichloroacetamide) (S3-6), "AD-67" or "MON 4660" (3-dichloroacetyl-1-oxa-3-aza-spiro[4.5]decane) (S3-7), "TI-35" (1-dichloroacetylazepane) (S3-8), "Diclonon" (dicyclonon) (S3-9), ((RS)-1-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[1,2-a]pyrimidin-6-one), "Furilazol" or "MON 13900" ((RS)-3-dichloroacetyl-5-(2-furyl)-2,2-dimethyl-oxazolidine) (S3-10), and its (R)-isomer (S3-11).

[0037] S4) Compounds of the group of acylsulfonamides (S4):

[0038] S4 a ) Equation (S4 a ) and their salts, which are described in WO-A-97 / 45016.

[0039] [ka]

[0040] [During the ceremony,

[0041] R A 1 is (C1-C6)-alkyl, (C3-C6)-cycloalkyl, where the last two mentioned radicals are selected from the group consisting of halogen, (C1-C4)-alkoxy, halo-(C1-C6)-alkoxy and (C1-C4)-alkylthio, and further, in the case of cyclic radicals, from the group consisting of (C1-C4)-alkyl and (C1-C4)-haloalkyl. A is substituted with a substituent of

[0042] R A 2 is halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, CF3;

[0043] m A is 1 or 2;

[0044] v D is 0, 1, 2 or 3;

[0045] S4 b ) The following formula (S4 b ) and their salts, which are described in WO-A-99 / 16744.

[0046] [ka]

[0047] [During the ceremony,

[0048] R B 1 , R B 2 are, independently of one another, hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C3-C6)-alkenyl, (C3-C6)-alkynyl,

[0049] R B 3 is halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl or (C1-C4)-alkoxy,

[0050] m B is either 1 or 2, for example,

[0051] R B 1 = cyclopropyl, R B 2 = hydrogen and (RB 3 ) = 2-OMe ("cyprosulfamide", S4-1),

[0052] R B 1 = cyclopropyl, R B 2 = hydrogen and (R B 3 ) = 5-Cl-2-OMe (S4-2),

[0053] R B 1 = ethyl, R B 2 = hydrogen and (R B 3 )=2-OMe(S4-3),

[0054] R B 1 = isopropyl, R B 2 = hydrogen and (R B 3 ) = 5-Cl-2-OMe (S4-4) and

[0055] R B 1 = isopropyl, R B 2 = hydrogen and (R B 3 )=2-OMe(S4-5)〕;

[0056] S4 c ) Equation (S4 c ) of the benzoylsulfamoylphenylurea class, which are described in EP-A-365484,

[0057] [ka]

[0058] [During the ceremony,

[0059] R C 1 , R C2 are independently of one another hydrogen, (C1-C8)-alkyl, (C3-C8)-cycloalkyl, (C3-C6)-alkenyl, (C3-C6)-alkynyl,

[0060] R C 3 is halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, CF3, m C is 1 or 2.

[0061] for example,

[0062] 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea;

[0063] 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea;

[0064] 1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea;

[0065] S4 d ) Equation (S4 d ) and salts thereof (which are known, for example, from CN 101838227),

[0066] [ka]

[0067] [During the ceremony,

[0068] R D 4 is halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, CF3;

[0069] m D is 1 or 2;

[0070] R D 5 is hydrogen, (C1-C6)-alkyl, (C3-C6)-cycloalkyl, (C2-C6)-alkenyl, (C2-C6)-alkynyl, (C5-C6)-cycloalkenyl.

[0071] S5) Active compounds (S5) selected from the classes of the hydroxyaromatic compounds and aromatic-aliphatic carboxylic acid derivatives, such as, for example, ethyl 3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicyclic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid (these are described in WO-A-2004 / 084631, WO-A-2005 / 015994, WO-A-2005 / 016001).

[0072] S6) Active compounds (S6) selected from the class of the 1,2-dihydroquinoxalin-2-ones, such as 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one, 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-thione, 1-(2-aminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one hydrochloride, 1-(2-methylsulfonylaminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one (which are described in WO-A-2005 / 112630).

[0073] S7) Compounds from the class of the diphenylmethoxyacetic acid derivatives (S7), such as, for example, methyl diphenylmethoxyacetate (CAS-Reg.Nr.41858-19-9) (S7-1), ethyl diphenylmethoxyacetate or diphenylmethoxyacetic acid (which are described in WO-A-98 / 38856).

[0074] S8) Compounds of formula (S8), which are described in WO?A?98 / 27049, [ka] [wherein the symbols and indices have the following meanings:

[0075] R D 1 is halogen, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy,

[0076] R D 2 is hydrogen or (C1-C4)-alkyl,

[0077] R D 3 is hydrogen, (C1-C8)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl or aryl, in which each of the aforementioned carbon-containing groups is unsubstituted or substituted with one or more, preferably up to three, identical or different groups selected from the group consisting of halogen and alkoxy, or a salt thereof,

[0078] n D is an integer from 0 to 2.

[0079] S9) Active compounds (S9) selected from the class of the 3-(5-tetrazolylcarbonyl)-2-quinolones, such as 1,2-dihydro-4-hydroxy-1-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No.: 219479-18-2), 1,2-dihydro-4-hydroxy-1-methyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No.: 95855-00-8) (which are described in WO-A-1999 / 000020).

[0080] S10) Compounds of formula (S10a) or (S10b) (which are described in WO-A-2007 / 023719 and WO-A-2007 / 023764),

[0081] [ka] [During the ceremony,

[0082] R E 1 is halogen, (C1-C4)-alkyl, methoxy, nitro, cyano, CF3, OCF3,

[0083] Y E , Z E are, independently of each other, O or S;

[0084] n E is an integer from 0 to 4,

[0085] R E 2 is (C1-C 16 )-alkyl, (C2-C6)-alkenyl, (C3-C6)-cycloalkyl, aryl, benzyl, halobenzyl;

[0086] R E 3 is hydrogen or (C1-C6)-alkyl.

[0087] S11) Active compounds of the oxyimino compound type (S11), which are known as seed dressing agents, e.g.

[0088] "Oxabetrinil" ((Z)-1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (S11-1), which is known as a seed dressing safener for millet / sorghum against injury by metolachlor;

[0089] "Fluxofenim" (1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethanone O-(1,3-dioxolan-2-ylmethyl)oxime) (S11-2), which is a known seed dressing safener for millet against damage by metolachlor, and

[0090] "Siometrinil" or "CGA-43089" ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (S11-3), which is a known seed dressing safener for millet against injury by metolachlor.

[0091] S12) Active compounds (S12) selected from the class of isothiochromanones, such as methyl [(3-oxo-1H-2-benzothiopyran-4(3H)-ylidene)methoxy]acetate (CAS Reg. No.: 205121-04-6) (S12-1) and related compounds (WO-A-1998 / 13361).

[0092] S13) One or more compounds selected from the following group (S13):

[0093] "Naphthalic anhydride" (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as a seed dressing safener for corn against injury caused by thiocarbamate herbicides;

[0094] "Fenclorim" (4,6-dichloro-2-phenylpyrimidine) (S13-2), which is known as a safener for pretilachlor in sown rice;

[0095] "Flurazole" (2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate benzyl) (S13-3), which is known as a seed dressing safener for millet against injury by alachlor and metolachlor;

[0096] "CL 304415" (CAS Reg. No.: 31541-57-8) (4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4) from American Cyanamid, which is known as a safener for corn against injury from imidazolinones;

[0097] "MG 191" (CAS Reg. No.: 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5), which is known as a safener for corn;

[0098] "MG 838" (CAS Reg. No.: 133993-74-5) (2-propenyl 1-oxa-4-azaspiro[4.5]decane-4-carbodithioate) (S13-6);

[0099] "Disulfoton" (O,O-diethyl S-2-ethylthioethyl phosphorodithioate) (S13-7);

[0100] "Dietholate" (O,O-diethyl O-phenylphosphorothioate) (S13-8);

[0101] “Mephenate” (4-chlorophenyl methylcarbamate) (S13-9).

[0102] S14) Active compounds which have a herbicidal effect against harmful plants as well as a phytotoxicity reducing effect against crop plants such as rice, e.g.

[0103] "Dimepyrate" or "MY 93" (S-1-methyl-1-phenylethyl piperidine-1-carbothioate), which is known as a safener for rice against molinate herbicide injury;

[0104] "Dymron" or "SK 23" (1-(1-methyl-1-phenylethyl)-3-p-tolyl urea), which is known as a safener for rice against imazosulfuron herbicide injury;

[0105] "Cumyluron" = "JC 940" (3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenylethyl)urea, (see JP-A-60087254), which is known as a safener for rice against injury from several herbicides;

[0106] "Methoxyphenone" or "NK 049" (3,3'-dimethyl-4-methoxybenzophenone), which is known as a safener for rice against injury from some herbicides;

[0107] "CSB" (1-Bromo-4-(chloromethylsulfonyl)benzene) from Kumiai (CAS Reg. No. 54091-06-4), which is known as a safener against injury of some herbicides in rice.

[0108] S15) Compounds of formula (S15) or tautomers thereof (which are described in WO-A-2008 / 131861 and WO-A-2008 / 131860)

[0109] [ka] [During the ceremony,

[0110] R H 1 is (C1-C6)-haloalkyl,

[0111] R H 2 is hydrogen or a halogen,

[0112] R H 3 , R H 4 are each independently hydrogen, (C1-C 16 )-Alkyl, (C2-C 16 )-alkenyl or (C2-C 16 )-alkynyl,

[0113] wherein the last three groups mentioned are each unsubstituted or substituted by one or more groups selected from the group consisting of halogen, hydroxy, cyano, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy, (C1-C4)-alkylthio, (C1-C4)-alkylamino, di[(C1-C4)-alkyl]amino, [(C1-C4)-alkoxy]carbonyl, [(C1-C4)-haloalkoxy]carbonyl, unsubstituted or substituted (C3-C6)-cycloalkyl, unsubstituted or substituted phenyl and unsubstituted or substituted heterocyclyl,

[0114] or (C3-C6)-cycloalkyl, (C4-C6)-cycloalkenyl, (C3-C6)-cycloalkyl (wherein the ring is fused at one side of the ring to a 4-6-membered saturated or unsaturated carbocyclic ring), or (C4-C6)-cycloalkenyl (wherein the ring is fused at one side of the ring to a 4-6-membered saturated or unsaturated carbocyclic ring),

[0115] wherein the last four groups are each unsubstituted or substituted with one or more groups selected from the group consisting of halogen, hydroxyl, cyano, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy, (C1-C4)alkylthio, (C1-C4)alkylamino, di[(C1-C4)alkyl]amino, [(C1-C4)alkoxy]carbonyl, [(C1-C4)haloalkoxy]carbonyl, unsubstituted or substituted (C3-C6)cycloalkyl, unsubstituted or substituted phenyl, and unsubstituted or substituted heterocyclyl; or

[0116] R H 3is (C1-C4)-alkoxy, (C2-C4)-alkenyloxy, (C2-C6)-alkynyloxy or (C2-C4)-haloalkoxy; and

[0117] R H 4 is hydrogen or (C1-C4)-alkyl; or

[0118] R H 3 and R H 4 together with the directly attached N-atom, is a 4-8 membered heterocyclic ring which in addition to the N-atom can contain further hetero ring atoms, preferably up to two further ring heteroatoms selected from the group consisting of N, O and S, and which heterocyclic ring is unsubstituted or substituted with one or more groups selected from the group consisting of halogen, cyano, nitro, (C1-C4)-alkyl, (C1-C4)-haloalkyl, (C1-C4)-alkoxy, (C1-C4)-haloalkoxy and (C1-C4)-alkylthio.

[0119] Pesticide Active Compounds

[0120] The pesticide active compounds used in the context of the present invention are known per se and are described, inter alia, in "The Pesticide Manual", 16th Edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012, and in the references cited therein.

[0121] The preferredIn the compositions (used) according to the invention the safeners are fenchlorazole-ethyl (S1), mefenpyr-diethyl (S2), isoxadifen-ethyl (S3), cyprosulfamide (S4), cloquintocet-mexyl (S5), fenclorim (S6), dichlormid (S7), benoxacor (S8), furilazole (S9), oxabetrinil (S10), fluxofenim (S11), flurazole (S12) or naphthalic anhydride (S13).

[0122] More preferably, In the compositions according to the invention (used) mefenpyr-diethyl (S2), isoxadifen-ethyl (S3), cyprosulfamide (S4) or cloquintocet-mexyl (S5) are the safeners.

[0123] Most preferred is In the compositions according to the invention (used) mefenpyr-diethyl (S2) or cloquintocet-mexyl (S5) are the safeners.

[0124] According to the present invention Moreover, most preferred An embodiment is a composition comprising: (i) ethofumesate of formula (I); and (ii) mefenpyr-diethyl as a safener.

[0125] The weight ratio of the composition (used) according to the invention can be described by the weight of the total amount of component (i) to the total amount of component (ii) and is in the range of 6:1 to 1:4, typically said ratio is in the range of 4:1 to 1:2.

[0126] Preferably, The weight ratio of the total amount of component (i) to the total amount of component (ii) in the composition (used) according to the invention is in the range of 3:1 to 1:2, typically the preferred ratio is in the range of 3:1 to 2:3.

[0127] More preferably,The weight ratio of the total amount of component (i) to the total amount of component (ii) in the composition (used) according to the invention is in the range of 5:2 to 2:3, typically more preferably in the range of 5:2 to 1:1.

[0128] The weight ratio of the total amount of component (i) to the total amount of component (ii) in the composition (use) according to the invention may also be in the range of 2:1 to 1:2, and in such cases, typically said ratio is in the range of 2:1 to 1:1.

[0129] Most preferably, The weight ratio of the total amount of component (i) to the total amount of component (ii) in the composition (used) according to the invention is about 1:1 or exactly 1:1, or the most preferred weight ratio of the total amount of component (i) to the total amount of component (ii) in the composition (used) according to the invention is about 2:1 or exactly 2:1, or the most preferred weight ratio of the total amount of component (i) to the total amount of component (ii) in the composition (used) according to the invention is about 3:2 or exactly 3:2, or the most preferred weight ratio of the total amount of component (i) to the total amount of component (ii) in the composition (used) according to the invention is about 5:2 or exactly 5:2.

[0130] Independent experiments have shown that a weight ratio of the total amount of component (i) to the total amount of component (ii) in the (used) composition according to the invention of approximately 3:2 or exactly 3:2 is particularly advantageous in the context of the present invention.

[0131] Independent experiments have also shown that a weight ratio of the total amount of component (i) to the total amount of component (ii) in the (used) composition according to the invention of approximately 5:2 or exactly 5:2 is particularly advantageous in the context of the present invention.

[0132] The properties and advantages described are the use for controlling harmful plants or undesirable vegetation and thus for protecting and / or increasing yields in terms of quality and quantity. Technical standards are clearly exceeded by these new combinations with regard to the properties described.

[0133] The compositions (used) according to the invention can be used to control harmful plants in genetically modified wheat crops or wheat crops obtained by mutation / selection. These crops are generally distinguished by certain advantageous properties, such as resistance to herbicide combinations / compositions, or resistance to plant diseases or causative agents of plant diseases, such as certain insects or microorganisms, such as fungi, bacteria or viruses. Other specific properties relate, for example, to the harvested material in terms of quantity, quality, storability, composition and specific components. Thus, for example, transgenic plants are known in which the starch content is increased or the starch quality is altered, or the harvested material has a different fatty acid composition.

[0134] The present invention also relates to a method for controlling harmful plants or unwanted vegetation, which comprises applying to the harmful plants or unwanted vegetation, to parts of said harmful plants or unwanted vegetation, or to the area in which the harmful plants or unwanted vegetation grow, for example to the area under cultivation, a composition (used) according to the invention by pre-emergence, early post-emergence or post-emergence treatment.The compositions of the present invention are also useful for seed treatment, in particular for seed treatment of cereals such as wheat, barley, rye, oats and millet, in particular wheat and barley, in particular winter wheat and winter barley.

[0135] In the context of the present invention, "controlling" means a significant reduction in the growth of harmful plants compared to untreated harmful plants. Preferably, the growth of harmful plants is essentially reduced (60-79%), more preferably the growth of harmful plants is largely or completely inhibited (80-100%), in particular the growth of harmful plants is almost or completely inhibited (90-100%).

[0136] When the composition (used) according to the invention is applied to the soil surface before or after the emergence of the plants but before their emergence from the soil, the treatment is a pre-emergence treatment.

[0137] When the composition (as used) according to the invention is applied to the soil surface after plant emergence, the treatment is a post-emergence treatment.

[0138] In the context of the present invention The preferred The use of the composition as defined herein in wheat crop plants, preferably selected from the group consisting of durum wheat (Tritricum durum) and bread wheat (Tritricum aestivum), in particular winter wheat, such as soft winter wheat (TRZAW).Also preferred in the context of the present invention is the use of the composition as defined herein in barley (Hordeum vulgare) crop plants, preferably winter barley (HORVW).

[0139] The application rates (expressed in g / ha, i.e. grams of active ingredient per hectare) of components (i), (ii) defined in the context of the present invention are as follows:

[0140] [Table 1]

[0141] Particularly preferred in the context of the present invention are compositions, uses and methods as described herein, wherein the application rate of component (i) ethofumesate is between 300 and 100 g / ha and the application rate of component (ii) safener, preferably mefenpyr-diethyl, is between 100 and 50 g / ha.

[0142] The compositions (used) according to the invention have outstanding herbicidal activity against a broad spectrum of economically important harmful monocotyledonous and dicotyledonous harmful plants occurring in wheat crops and in fields where wheat crops are growing or are intended to be grown.

[0143] In the context of this specification, reference is made to the BBCH scale (especially for cereals) and the BBCH growth stages which describe the phenological stages of (cereal) crop plants using the BBCH scale according to the BBCH monograph "Growth stages of mono- and dicotyledonous plants", 2nd Edition, 2001, edited by Uwe Meier, Federal Biological Research Centre for Agriculture and Forestry (Biologische Bundesanstalt für Land und Forstwirtschaft).

[0144] The following BBCH serial growth steps are of particular relevance in the context of the present invention:

[0145] [Table 2]

[0146] In the context of the present invention, cereal crops such as wheat, barley, rye, oats and millet, in particular wheat and barley, in particular winter wheat and winter barley, are of particular interest.

[0147] In particular, some representative examples of monocotyledonous and dicotyledonous weed flora that can be controlled by the compositions (used) according to the invention can be mentioned, without the list being limited to specific species.

[0148] Examples of harmful monocotyledonous plants against which the compositions (used) according to the invention can be effectively applied are barley (Hordeum spp.), barnyard grass (Echinochloa spp.), Poa spp., Bromus spp., Digitaria spp., Eriochloa spp., Setaria spp., Pennisetum spp., Eleusine spp., Eragrostis spp., Panicum spp., Lolium spp., Alopecurus spp., Apera spp., and the like. sp.), Brachiaria spp., Leptochloa spp., Avena spp., Cyperus spp., Axonopris spp., Sorghum spp., Phalaris sp. and Melinus spp.

[0149] Specific examples of harmful monocotyledonous plant species against which the compositions (used) according to the invention can be effectively acted upon are: Hordeum murinum, Echinochloa crus-galli, Poa annua, Bromus rubens L., Bromus rigidus, Bromus secalinus L., Digitaria insularis, Digitaria sanguinalis, Eriochloa gracilis, Setaria faberi, Setaria viridis, Pearl millet, Eleusine indica, Eragrostis pectinacea, and the like. pectinacea, Panicum miliaceum, Lolium sp., Brachiaria platyphylla, Leptochloa fusca, Avena fatua, Cyperus compressus, Cyperus esculentes, Axonopris offinis, Sorghum halapense, Alopecurus myosuroides, Apera spica-venti and Melinus repens.

[0150] Specific examples of harmful monocotyledonous plant species particularly relevant for cereal (particularly wheat) crops on which the compositions (used) according to the invention act effectively are Poa annua, Bromus rubens L., Bromus rigidus, Bromus secalinus L., Lolium sp., Avena fatua, Alopecurus myosuroides, Apera spica-venti and Phalaris minor.

[0151] Examples of dicotyledonous harmful plants against which the compositions (used) according to the invention can be effectively acted upon are Amaranthus spp., Polygonum spp., Medicago spp., Mollugo spp., Cyclospermum spp., Stellaria spp., Gnaphalium spp., Taraxacum spp., Oenothera spp., Amsinckia spp., Erodium spp., Erigeron spp., Senecio spp., Lamium spp., spp.), Kochia spp., Chenopodium spp., Lactuca spp., Malva spp., Ipomoea spp., Brassica spp., Sinapis spp., Urtica spp., Sida spp., Portulaca spp., Richardia spp., Ambrosia spp., Calandrinia spp., Sisymbrium spp., Sesbania spp., spp.), Capsella spp., Sonchus spp., Euphorbia spp., Helianthus spp., Coronopus spp., Salsola spp., Abutilon spp., Vicia spp., Epilobium spp., Cardamine spp., Picris spp., Trifolium spp., Galinsoga spp., Epimedium spp.), Marchantia spp., Solanum spp., Oxalis spp., Metricaria spp., Plantago spp., Tribulus spp., Cenchrus spp., Bidens spp., Veronica spp. and Hypochaeris spp..

[0152] Specific examples of harmful dicotyledonous plant species on which the compositions (used) according to the invention can be effectively acted upon are Amaranthus spinosus, Amaranthus palmer, Amaranthis rudis, Polygonum convolvulus, Medicago polymorpha, Mollugo verticillata, Cyclospermum leptophyllum, Stellaria media, Gnaphalium purpureum, Taraxacum officinale, Oenothera laciniata, Amsinckia intermedia, Erodium cicutarium, Musk Geranium (Erodium moschatum), Raspberry (Erigeron bonariensis), Groundsel (Senecio vulgaris), Lamium sp.), Erigeron canadensis, Polygonum aviculare, Kochia scoparia, Chenopodium album, Lactuca serriola, Malva parviflora, Malva neglecta, Ipomoea hederacea, Ipomoea lacunose, Brassica nigra, Sinapis arvensis, Urtica dioica, Amaranthus blitoides, Amaranthus retroflexus, Amaranthus hybridus, Amaranthus lividus, Sida spinosa, Portulaca oleracea, Richardia scabra, Ambrosia artemisiifolia, Calandrinia caulescens, Sisymbrium irio, Sesbania exaltata, Capsella bursa-pastoris, Sonchus oleraceus, Euphorbia maculate, Helianthus annuus, Coronopus didymus, Salsola tragus, Abutilon theophrasti, Vicia benghalensis L. L.), Epilobium paniculatum, Cardamine spp., Picris echioides, Trifolium spp., Galinsoga spp., Epimedium spp.), Marchantia spp., Solanum spp., Oxalis spp., Matricaria chamomilla, Plantago spp., Tribulus terrestris, Salsola kali, Cenchrus spp., Bidens bipinnata, Veronica sp., Galium aparine L., Papaver rhoeas, Viola arvense, Centaurea cyanus and Hypochaeris radicata.

[0153] Specific examples of harmful dicotyledonous plant species, particularly relevant for cereal (particularly wheat) crops, on which the compositions (used) according to the invention act effectively are Stellaria media, Senecio vulgaris, Lamium sp., Polygonum aviculare, Kochia scoparia, Chenopodium album, Brassica nigra, Sinapis arvensis, Capsella bursa-pastoris, Sonchus oleraceus, Matricaria chamomilla, Veronica sp., Galium aparine L., Papaver rhoeas, Viola arvensis, and the like. arvense) and the common cornflower (Centaurea cyanus).

[0154] The composition (used) according to the invention is easily and quickly obtained by mixing components (i) and (ii) in the weight and ratios defined in the context of the present invention, e.g. appropriate amounts of components (i) and (ii).

[0155] Thus, in a further aspect, the present invention relates to a method for producing a composition (for use) according to the invention, comprising:

[0156] (a) providing component (i);

[0157] (b) providing component (ii);

[0158] (c) combining component (i) with component (ii)

[0159] The present invention relates to a method for producing a composition (used) according to the invention, comprising:

[0160] Components (i) and (ii) present in the composition (used) according to the invention may be applied once, twice or three times per Gregorian calendar year, i.e. once, twice or three times per Gregorian calendar year.

[0161] The (used) composition according to the invention may further comprise one or more further ingredients selected from the group consisting of formulation auxiliaries and formulation additives customary in crop protection.

[0162] Furthermore, components (i) and (ii) as defined herein can be used together with formulation auxiliaries and additives customary in crop protection, such as, for example, fertilizers and colorants.

[0163] The (used) compositions according to the invention can be used not only as mixed formulations, which are applied in the customary manner with water as diluent, but also as so-called tank mixes by diluting separately formulated or partly separately formulated components together with water, thereby obtaining a ready-to-use application spray mixture.

[0164] Such a tank mix can for example be obtained by combining (i) a formulation of ethofumesate, e.g., a formulation of ethofumesate containing a total amount of ethofumesate in the range of 100 g / L to 600 g / L, e.g., a commercial SC formulation containing 500 g / L of ethofumesate, and (ii) a formulation of a safener, e.g., a formulation containing (ii) a safener in a total amount in the range of 50 g / L to 600 g / L, and diluting it with an appropriate amount of water to obtain a ready-to-use application spray mixture.

[0165] The compositions (used) according to the invention can be formulated in various ways, depending on the general biological and / or chemical-physical parameters. The following are examples of typical possible formulations: wettable powders (WP), water-soluble concentrates, emulsifiable concentrates (EC), aqueous solutions (SL), emulsifiable concentrates (EW) such as aqueous emulsions and oil emulsions, sprayable solutions or emulsions, suspension concentrates (SC), oil-dispersible wettable powders (OD), oil- or water-based dispersions, suspoemulsions, dusts (DP), seed dressing materials, granules for soil application or for dusting, or wettable granules (WG), ULV formulations, microcapsules (e.g. CS, ZC) or waxes.

[0166] The individual formulation types are known in principle and are described, for example, in Winnacker-Kuechler, "Chemische Technologie", Volume 7, CHauser Verlag Munich, 4th edition, 1986; van Valkenburg, "Pesticide Formulations", Marcel Dekker NY, 1973; K. Martens, "Spray Drying Handbook", 3rd edition, 1979, G. Goodw Ltd. London.

[0167] Necessary formulation auxiliaries such as inert materials, surfactants, solvents and other additives are also known and are 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, NY Marsden, "Solvents Guide", 2nd ed., Interscience, NY 1950; McCutcheon's, "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood NJ; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., NY 1964; Schoenfeldt, "Grenzflaechenaktive Aethylenoxidaddukte" [Surface Active Ethylene Oxide Adducts], Wiss. Verlagsgesellschaft, Stuttgart 1976, Winnacker-Kuechler, "Chemische Technologie", Volume 7, C.Hauser Verlag Munich, 4th edition 1986.

[0168] Wettable powders (sprayable powders) are products which are homogeneously dispersible in water and which, besides the active compound, contain, in addition to diluents or inert substances, ionic or nonionic surfactants (wetting agents, dispersants), for example polyoxyethylated alkylphenols, polyethoxylated fatty alcohols, polyethoxylated fatty amines, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, sodium 2,2'-dinaphthylmethane-6,6'-disulfonate, sodium dibutylnaphthalenesulfonate or sodium oleoyl methyl taurate.

[0169] Emulsifiable concentrates are prepared by dissolving the active compounds in an organic solvent (e.g. butanol, cyclohexanone, dimethylformamide, xylene or aromatic substances or hydrocarbons with relatively high boiling points) with the addition of one or more surfactants (emulsifiers), ionic and / or non-ionic. Examples of emulsifiers which may be used are: calcium alkylarylsulfonates, e.g. calcium dodecylbenzenesulfonate, or non-ionic emulsifiers, e.g. fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide / ethylene oxide condensates, alkyl polyethers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters or polyoxyethylene sorbitol esters.

[0170] Dusts are obtained by grinding the active compound with finely divided solid materials, for example talc, natural clays, such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.

[0171] Suspension concentrates (SC) can be aqueous or oil-based. They can be prepared, for example, by wet-grinding using a commercial bead mill and, optionally, with the addition of a surfactant (such as those already mentioned above for the other formulation types).

[0172] Emulsions, e.g., aqueous emulsions (EW), can be prepared, for example, using aqueous organic solvents and, optionally, surfactants (e.g., those already mentioned above for the other formulation types), using stirrers, colloid mills and / or static mixers.

[0173] Granules can be produced by spraying the active compound onto the surface of an adsorbent granular inert material or by applying an active compound concentrate onto the surface of a carrier (e.g. sand, kaolinite or granular inert material) with an adhesive (e.g. polyvinyl alcohol, sodium polyacrylate or mineral oil). It is also possible to granulate suitable active compounds (if necessary as a mixture with fertilizers) in a conventional manner for producing fertilizer granules. In principle, water-dispersible granules are prepared by conventional methods such as spray drying, fluidized bed granulation, disk granulation, mixing with high-speed mixers and extrusion without solid inert materials. For the preparation of disk granulations, fluidized bed granulations, extrusion granulations and spray granulations, see, for example, the methods described in "Spray-Drying Handbook", 3rd Edition, 1979, G. Goodwin Ltd., London; JE Browning, "Agglomeration", Chemical and Engineering 1967, pp. 147 ff.; "Perry's Chemical Engineer's Handbook", 5th Edition, McGraw Hill, New York 1973, pp. 8-57.

[0174] For further details regarding the formulation of crop protection compositions, see, for example, G.C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pp. 81-96 and J.D. Freyer, S.A. Evans, "Weed Control Handbook", 5th ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.

[0175] As a rule, pesticide formulations contain from 1 to 95% by weight of active compound, the following concentrations are customary, depending on the type of formulation:

[0176] The active compound concentration in wettable powders (powders) is, for example, about 10-95% by weight, the remainder up to 100% by weight being composed of customary formulation components. In the case of emulsifiable concentrates, the active compound concentration can be, for example, in an amount of 5-80% by weight. Formulations in the form of dusts in most cases contain 5-20% by weight of active compound, sprayable solutions contain about 0.2-25% by weight of 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 which granulation auxiliaries and fillers are used. As a rule, the content is 10-90% by weight for wettable granules.

[0177] Furthermore, the active compound formulations described above may, if appropriate, contain conventional adhesives, wetting agents, dispersants, emulsifiers, preservatives, antifreeze agents, solvents, fillers, colorants, carriers, antifoaming agents, evaporation inhibitors, pH regulators or viscosity regulators.

[0178] The herbicidal action of the herbicide(s) present in the (used) composition according to the invention can be improved, for example, by surfactants, preferably by wetting agents from the group of the fatty alcohol polyglycol ethers. The fatty alcohol polyglycol ethers preferably contain 10 to 18 carbon atoms in the fatty alcohol radical and 2 to 20 ethylene oxide units in the polyglycol ether moiety. The fatty alcohol polyglycol ethers can be non-ionic or ionic, for example in the form of fatty alcohol polyglycol ether sulfates, which can be used, for example, as alkali metal salts (for example sodium or potassium salts) or ammonium salts, but also as alkaline earth metal salts, such as magnesium salts, for example sodium C 12 / C 14- fatty alcohol diglycol ether sulfates (Genapol® LRO, Clariant); see for example EP-A-0476555, EP-A-0048436, EP-A-0336151, or see also US-A-4,400,196 and Proc. EWRS Symp. "Factors Affecting Herbicidal Activity and Selectivity", 227-232 (1988). Non-ionic fatty alcohol polyglycol ethers contain, for example, 2 to 20, preferably 3 to 15, ethylene oxide units (C 10 -C 18 )-, preferably (C 10 -C 14 ) - fatty alcohol polyglycol ethers (for example isotridecyl alcohol polyglycol ethers), for example those from the Genapol® series, such as Genapol® X-030, Genapol® X-060, Genapol® X-080 or Genapol® X-150 (all from Clariant GmbH).

[0179] The present invention further encompasses the (use of) the combination of the above-mentioned wetting agents from the group of the aliphatic alcohol polyglycol ethers, which preferably contain 10 to 18 carbon atoms in the aliphatic alcohol group and 2 to 20 ethylene oxide units in the polyglycol ether moiety and which may be present in non-ionic or ionic form (for example as aliphatic alcohol polyglycol ether sulfates), with components (i) and (ii) as defined above. 12 / C 14- sodium fatty alcohol diglycol ether sulfate (Genapol® LRO, Clariant); and isotridecyl alcohol polyglycol ethers having 3 to 15 ethylene oxide units, such as those of the Genapol® series, for example Genapol® X-030, Genapol® X-060, Genapol® X-080 or Genapol® X-150 (all from Clariant GmbH), are preferred. Furthermore, fatty alcohol polyglycol ethers, such as non-ionic or ionic fatty alcohol polyglycol ethers (e.g. fatty alcohol polyglycol ether sulfates), are also known to be suitable for use as penetrants and activity enhancers for many other herbicides, especially those from the group of the imidazolinone series (see, for example, EP-A-0502014).

[0180] Furthermore, fatty alcohol polyglycol ethers, such as non-ionic or ionic fatty alcohol polyglycol ethers (e.g. fatty alcohol polyglycol ether sulfates), are also known to be suitable for use as penetrants and activity enhancers for many other herbicides, especially those from the group of the imidazolinone series (see, for example, EP-A-0502014).

[0181] The herbicidal effect of the composition (used) according to the invention can also be increased by using vegetable oil.The term vegetable oil should be understood to mean oil derived from oil-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 their transesterification products, such as alkyl esters, such as rapeseed oil methyl ester or rapeseed oil ethyl ester.

[0182] The vegetable oil is preferably C 10 -C 22 -, preferably C 12 -C 20-Esters of fatty acids. 10 -C 22 -Fatty acid esters can be, for example, unsaturated or saturated C 10 -C 22 - esters of fatty acids, in particular those having an even number of carbon atoms, such as erucic acid, lauric acid, palmitic acid, and in particular C 18 fatty acids, such as stearic acid, oleic acid, linoleic acid or linolenic acid.

[0183] Preferred C1-C 20 -Alkyl-C 10 -C 22 - Fatty acid esters are methyl, ethyl, propyl, butyl, 2-ethylhexyl and dodecyl esters. Preferred glycol- and glycerol-C 10 -C 22 -Fatty acid esters are C 10 -C 22 - homogeneous or mixed glycol and glycerol esters of fatty acids, in particular fatty acids having an even number of carbon atoms, such as erucic acid, lauric acid, palmitic acid, and especially C 18 fatty acids, such as stearic acid, oleic acid, linoleic acid or linolenic acid.

[0184] The vegetable oil may be present in the herbicidal composition (used) according to the invention, for example in the form of commercially available oil-containing formulation additives, in particular those based on rapeseed oil, such as Hasten® (Victorian Chemical Company, Australia, hereinafter referred to as Hasten, main component: rapeseed oil ethyl ester), Actirob® B (Novance, France, hereinafter referred to as Actirob B, main component: rapeseed oil methyl ester), Rako-Binol® (Bayer AG, Germany, hereinafter referred to as Rako-Binol, main component: rapeseed oil), Renol® (Stefes, Germany, hereinafter referred to as Renol, vegetable oil component: rapeseed oil methyl ester) or Stefes Mero® (Stefes, Germany, main component: rapeseed oil methyl ester).

[0185] For use, the formulations containing components (i) and (ii) present in the (used) compositions according to the invention are optionally diluted in a conventional manner, for example with water in the case of wettable powders (dusts), emulsifiable concentrates, dispersions and water dispersible granules. Formulations in the form of dusts, soil granules, granules for spreading and sprayable solutions are usually not further diluted with other inert substances before use.

[0186] The compositions defined in the context of the present invention are preferably applied to harmful or undesirable plants or parts thereof, to the seeds of the plants or to the area under cultivation (field soil), preferably to the greenery of harmful plants or parts thereof, or to the green parts of undesirable plants or parts thereof.

[0187] The composition (used) according to the invention comprising components (i) and (ii) has the advantage that it is easier to apply, since the amounts of the components are already presented in the correct ratio to each other. Furthermore, the adjuvants in the formulation can be optimally matched to each other.

[0188] As already mentioned in more detail above, the present invention further relates to the (use of) a composition according to the invention comprising components (i) and (ii) (preferably one of the preferred, more preferred or particularly preferred embodiments as defined herein) in the agricultural field, in particular for controlling harmful plants or unwanted plant growth.

[0189] Thus, a further aspect of the invention relates to the use of a composition according to the invention for the protection of crop plants, preferably cereal crop plants, in particular wheat crop plants or barley crop plants.

[0190] Said use is preferably characterised in that said composition is applied after emergence to cereal plants, in particular wheat crop plants or barley crop plants.

[0191] The present invention also relates to a method for controlling undesirable vegetation, characterized in that a composition as defined in the context of the present invention is applied to the area in which the undesirable vegetation or crop plants are growing or will grow.

[0192] Said method is preferably characterized in that a composition as defined in the context of the present invention is applied to crop plants after emergence, preferably to cereal crop plants after emergence.

[0193] Said use or method is preferably characterized in that a composition as defined in the context of the present invention is applied in such a way that the amount of ethofumesate is in the range of 700 g / ha to 50 g / ha, preferably in the range of 600 g / ha to 50 g / ha, more preferably in the range of 500 g / ha to 100 g / ha, most preferably in the range of 300 g / ha to 100 g / ha.

[0194] Said use or method is preferably characterized in that the composition is applied to cereal crop plants after emergence before BBCH growth stage 13 of the cereal crop plants, preferably at BBCH growth stages 09, 10, 11 and / or 12, more preferably at BBCH growth stages 10, 11 and / or 12 of the cereal crop plants, in particular at BBCH growth stages 10, 11 or 12 of the cereal crop plants.

[0195] Said use or method is preferably characterized in that the (cereal) crop plant is a wheat crop plant or a barley crop plant.

[0196] Said use or method is preferably characterized in that the cereal crop plants are selected from the group consisting of durum wheat (Tritricum durum), bread wheat (Tritricum aestivum) and barley (Hordeum vulgare).

[0197] In a further aspect the present invention relates to the use of mefenpyr-diethyl or cloquintocet-mexyl as safener for ethofumesate, preferably in cereal crop plants, in particular wheat crop plants or barley crop plants. EXAMPLES

[0198] Working Example

[0199] Field trials investigated the interaction of (i) ethofumesate and (ii) the safener mefenpyr-diethyl on cereal crop injury.

[0200] Plots of different wheat and barley crops in the field were sprayed using a handheld spray boom at a rate of 140 L / ha.

[0201] Application of the spray compositions was carried out at BBCH growth stage 11 (first expanded leaf) of the respective wheat or barley crop, and in both cases early after emergence.

[0202] The four different soft winter wheat (TRZAW) varieties tested were ARTHUR NICK, ELIXER, PISTOLO and RUBISKO.

[0203] The three different winter barley (HORVW) varieties tested were CALIFORNIA, CIERZO and KWS ORBIT.

[0204] Maximum and final crop damage was visually assessed in each case on a percentage scale in relation to the untreated control (100% = all plants dead, complete crop mortality; 50% = 50% reduction in green plant biomass, and 0% = no crop damage, as in the control).

[0205] The main symptoms of crop damage observed were thinning and stunting.

[0206] Soft Winter Wheat Results - Maximum Crop Damage (%)

[0207] [Table 3]

[0208] Soft Winter Wheat Results - Final Crop Damage (%)

[0209] [Table 4]

[0210] Winter barley results - Maximum crop damage (%)

[0211] [Table 5]

[0212] Winter barley results - final crop damage (%)

[0213] [Table 6]

Claims

1. 1. A herbicidal composition comprising: (i) Ethofumesate and (ii) one or more safeners wherein components (i) and (ii) are present in a ratio ranging from 6:1 to 1:4, based on the total weight of the composition, and component (i) is the only herbicidally active ingredient.

2. 2. The composition according to claim 1, characterized in that component (ii) comprises or consists of mefenpyr-diethyl or cloquintocet-mexyl.

3. 3. A composition according to claim 1 or 2, characterised in that components (i) and (ii) are the only pesticidally active compounds present in the composition.

4. 2. The composition according to claim 1, characterized in that the weight ratio of the total amount of component (i) to the total amount of component (ii) is in the range of 4:1 to 1:2, preferably in the range of 3:1 to 1:2, each based on the total amount of the composition.

5. 2. The composition according to claim 1, characterized in that the weight ratio of the total amount of component (i) to the total amount of component (ii) is in the range of 5:2 to 1:2, preferably in the range of 5:2 to 1:1, each based on the total amount of the composition.

6. 2. The composition according to claim 1, further comprising one or more further ingredients selected from the group consisting of formulation auxiliaries and formulation additives customary in crop protection.

7. 2. Use of a composition according to claim 1 for the protection of crop plants, preferably cereal crop plants, in particular wheat crop plants or barley crop plants.

8. 8. Use according to claim 7, characterized in that the composition is applied post-emergence to cereal plants, in particular wheat or barley crop plants.

9. 13. A method for controlling undesirable vegetation, comprising applying the composition of claim 1 to the area in which the undesirable vegetation or crop plants are growing or will grow.

10. 10. The method according to claim 9, characterized in that the composition is applied post-emergence to the crop plants, preferably post-emergence to cereal crop plants.

11. 8. The use or method according to claim 7, characterized in that the composition is applied in such a way that the amount of ethofumesate is in the range of 700 g / ha to 50 g / ha, preferably in the range of 600 g / ha to 50 g / ha, more preferably in the range of 500 g / ha to 100 g / ha, most preferably in the range of 300 g / ha to 100 g / ha.

12. 8. The use or method according to claim 7, characterized in that the composition is applied to cereal crop plants after emergence before BBCH development stage 13, preferably at BBCH development stages 09, 10, 11 and / or 12 of the cereal crop plants.

13. 8. The use or method according to claim 7, characterized in that the crop plant is a wheat crop plant or a barley crop plant.

14. 8. The use or method according to claim 7, characterized in that the crop plant is selected from the group consisting of durum wheat (Tritricum durum), bread wheat (Tritricum aestivum) and barley (Hordeum vulgare).

15. Use of mefenpyr-diethyl or cloquintocet-mexyl as safener for ethofumesate, preferably in cereal crops, in particular in wheat or barley crop plants.

Images