Malonamide for selective weed control in cereal crops

Abstract

A method for selectively controlling weeds in a monocotyledonous crop, the method comprising applying to a crop cultivation area an effective amount of a herbicide A selected from the group consisting of a compound of formula (I) and a salt of a compound of formula (I); wherein R is hydrogen, (C1-C6)-alkyl or (C3-C6)-cycloalkyl.

Description

[0001] This invention relates to a method for selectively controlling weeds in monocotyledonous crops, particularly cereal crops, the method comprising applying an effective amount of malondiamide (herbicide A) to a cultivation area of ​​a monocotyledonous crop, preferably a cereal crop, in which weeds grow or may grow, as described herein.

[0002] The present invention also relates to the use of the herbicide A in monocotyledonous crops, particularly in cereal crops, for selective weed control. Background Technology

[0003] In crop protection products, it is generally desirable to increase the specificity and reliability of the active compound's action. Specifically, it is desirable for the crop protection product to effectively control harmful plants while simultaneously being tolerated by the beneficial plants in question. It is known that in some cases, better crop-plant compatibility can be achieved by combining a herbicide with a specific action with an organic active compound that acts as an antidote or antagonist. Because these antidotes or antagonists can reduce or even prevent damage to crop plants, they are also referred to as safeners.

[0004] WO 2018 / 228985 relates to the herbicidal activity of tetrahydrofuranic acid and dihydrofuranic acid and their esters, 3-phenylisoxazoline-5-carboxamide and its agrochemically acceptable salts, and to their use in the field of plant protection. According to WO 2021 / 245003, the compatibility of these compounds with crop plants is not entirely satisfactory under all conditions; therefore, a combination with the safener ethyl bis(phenyloxazoline) is proposed to prevent damage to crop plants.

[0005] Generally, preferred herbicides effectively control unwanted vegetation while simultaneously exhibiting acceptable phytotoxicity to crop plants.

[0006] WO 2021 / 170464 discloses certain malonamide compounds and compositions containing them for controlling unwanted vegetation. While these malonamide compounds exhibit excellent herbicidal activity, there remains a need for methods to selectively control weeds specifically in monocotyledonous crops, particularly cereal crops, that provide effective control of unwanted vegetation while being well tolerated by monocotyledonous crops such as cereals.

[0007] We have discovered that this objective and other objectives are achieved by a method comprising applying an effective amount of herbicide A to a cultivation area of ​​a monocotyledonous crop, preferably a cereal crop, the herbicide being selected from compounds having formula (I) and salts of compounds having formula (I).

[0008] ,

[0009] Wherein, R is hydrogen, (C1-C6)-alkyl, or (C3-C6)-cycloalkyl. Summary of the Invention

[0010] The object of the present invention is to provide a method for selectively controlling weeds in monocotyledonous crops, particularly cereal crops, using a herbicidal composition that allows for effective and reliable control of weeds growing or likely to grow in monocotyledonous crops, particularly cereal crops, while being well tolerated by said crops.

[0011] Furthermore, the method should allow for effective weed control in the crop without the need for safeners to prevent or reduce damage to monocot crops, particularly cereal crops.

[0012] In addition, the herbicidal activity of the composition should last long enough to achieve weed control over a sufficiently long period of time, thereby allowing for more flexible application.

[0013] Surprisingly, it has now been found that selective control of weeds growing or about to grow in monocotyledonous crops, particularly cereal crops, can be achieved by applying an effective amount of herbicide A, selected from compounds having formula (I) and salts of compounds having formula (I), to crop cultivation areas.

[0014] ,

[0015] Wherein, R is hydrogen, (C1-C6)-alkyl, or (C3-C6)-cycloalkyl.

[0016] In a preferred embodiment of the method according to the invention, an effective amount of herbicide A is applied to the crop cultivation area. Herbicide A is selected from compounds having formula (I) and salts of compounds having formula (I), wherein R is hydrogen, (C1-C3)-alkyl, or (C3-C5)-cycloalkyl.

[0017] In a more preferred embodiment of the method according to the invention, an effective amount of herbicide A is applied to the crop cultivation area. Herbicide A is selected from compounds having formula (I) and salts of compounds having formula (I), wherein R is hydrogen, methyl, ethyl, isopropyl, cyclopropyl or cyclobutyl, preferably hydrogen, methyl or isopropyl.

[0018] In a particularly preferred embodiment of the method according to the invention, the herbicide A applied to the crop cultivation area is a compound having formula (Ia) or a salt of a compound having formula (Ia).

[0019] .

[0020] In another particularly preferred embodiment of the method according to the invention, the herbicide A applied to the crop cultivation area is a compound having formula (Ib) or a salt of a compound having formula (Ib).

[0021] .

[0022] In another particularly preferred embodiment of the method according to the invention, the herbicide A applied to the crop cultivation area is a compound having formula (Ic) or a salt of a compound having formula (Ic).

[0023] .

[0024] In another particularly preferred embodiment of the method according to the invention, the herbicide A applied to the crop cultivation area is a compound having formula (Id) or a salt of a compound having formula (Id).

[0025] .

[0026] In another particularly preferred embodiment of the method according to the invention, the herbicide A applied to the crop cultivation area is a compound having formula (Ie) or a salt of a compound having formula (Ie).

[0027] .

[0028] In another particularly preferred embodiment of the method according to the invention, the herbicide A applied to the crop cultivation area is a compound having the formula (If) or a salt of a compound having the formula (If).

[0029] .

[0030] In the method according to the invention, the required amount of the pure active compound (i.e., herbicide A) depends on the density of the unwanted vegetation, the developmental stage of the plant, the climatic conditions of the site where herbicide A or a composition containing herbicide A is used, and the method of application.

[0031] Typically, the application rate of herbicide A is from 1 g / ha to 500 g / ha, preferably from 1 g / ha to 250 g / ha, and more preferably from 1 g / ha to 100 g / ha of active substance.

[0032] Herbicide (A) can generally be applied to weeds at any growth stage with good results. In one embodiment, application of herbicide (A) up to the BBCH growth stage 37 of the weeds showed effective weed control.

[0033] The BBCH growth stage is defined as follows: “Growth stage of monocotyledonous and dicotyledonous plants”, BBCH monograph edited by Uwe Meier Julius Kühn-Institut (JKI), Open Agrar Repositorium, Quedlinburg 2018 DOI: 10.5073 / 20180906-074619 ISBN: 978-3-95547-071-5.

[0034] This invention relates to a method for selectively controlling weeds in monocotyledonous crops, particularly cereal crops (including cereals, corn, sorghum, and rice).

[0035] In the method according to the invention for selectively controlling weeds in monocotyledonous crops, particularly cereal crops, the herbicide (A) can generally be applied before or after crop emergence.

[0036] The weeds controlled by the method according to the invention include monocotyledonous weeds (monocot plants) and dicotyledonous weeds (dicot plants), with monocotyledonous plants being preferred.

[0037] The method of the present invention for selectively controlling weeds in monocotyledonous crops, particularly cereal crops, has several advantages over methods of applying structurally similar herbicides:

[0038] The method of the present invention exhibits excellent crop compatibility with certain conventional crop plants, particularly monocotyledonous crops such as cereal crops. This is unexpected because the crops are monocotyledonous plants, such as grass weeds, which are controlled by the method according to the invention.

[0039] Therefore, the method of the present invention can also be applied after the crop seedlings have emerged, without the addition of a safener.

[0040] - The method of the present invention provides sufficient duration of weed-controlling activity, even under severe weathering conditions, allowing for more flexible application and minimizing the risk of weed escape. Detailed Implementation

[0041] This invention relates to a method for selectively controlling weeds in monocotyledonous crops, particularly cereal crops, the method comprising applying an effective amount of herbicide A to the crop cultivation area, the herbicide A being selected from compounds having formula (I) and salts of compounds having formula (I).

[0042] ,

[0043] Wherein, R is hydrogen, (C1-C6)-alkyl, or (C3-C6)-cycloalkyl.

[0044] The present invention also relates to compounds having formula (I). Furthermore, the present invention relates to agrochemical compositions for selective weed control in monocotyledonous crops, particularly cereal crops, comprising a compound having formula (I) and one or more adjuvants commonly used in crop protection compositions.

[0045] As used in this article, the terms “control” and “counter” are synonyms, referring to the inhibition, control, reduction or complete destruction of weed growth.

[0046] As used herein, the terms "composition of herbicide A" and "composition containing herbicide A" refer to any composition containing herbicide A. Different salts of herbicide A are considered to be the same herbicide compound.

[0047] As used herein, the term "agricultural chemical composition" refers to a composition of herbicide A (and compositions comprising herbicide A) and one or more adjuvants commonly used in crop protection compositions.

[0048] As used herein, "herbicide" means one or more reagents, compounds and / or compositions that have herbicidal and / or herbicidal activity.

[0049] As used herein, the terms “undesirable vegetation,” “undesirable species,” “undesirable plant,” “harmful plant,” “undesirable weed,” “native plant,” “weed,” or “harmful weed” are used synonymously.

[0050] As used herein, the term "effective amount" refers to the amount or quantity of herbicide A necessary to achieve the desired effect or result. The amount of herbicide A is sufficient to effectively control or eliminate the target weed or plant while minimizing any adverse effects on non-target organisms or the environment. Specific effective amounts can vary depending on factors such as the target plant species, application method, environmental conditions, and the required level of control.

[0051] As used in this article, "post-emergence" refers to herbicide treatment applied to areas where crop plants have already germinated and emerged from the ground or growing medium.

[0052] As used in this article, "pre-emergence" refers to herbicide treatment applied to areas where crop plants have already emerged from the ground or growing medium.

[0053] As used in this article, "de-germination" refers to the use of herbicides to reduce the presence of weeds during treatment. De-germination is typically used in minimally tilled or no-till fields because weeds cannot be controlled by tilling the soil. De-germination can be applied after harvest and / or before crop emergence. De-germination is particularly useful for weeds that appear between growing seasons.

[0054] Malonamide compounds having formula (I) (where R is hydrogen, (C1-C6)-alkyl, or (C3-C6)-cycloalkyl) are known from WO 2021 / 170464. In the method according to the invention, a malonamide compound having formula (I) is used, wherein the substituents of the cyclopentene are oriented in the same direction (preferably the cis-diastereomers Ia to If as shown below).

[0055]

[0056]

[0057]

[0058] .

[0059] .

[0060] .

[0061] .

[0062] Depending on the stereochemical orientation of the methoxy group (R or S), the cis-diastereomers Ia to If exist in different proportions as epimeric / diastereomer mixtures (IaR + IaS; IbR + IbS, IcR + IcS, IdR + IdS, IeR + IeS, IfR + IfS).

[0063] Therefore, compounds IaR, IaS, IbR, IbS, IcR, IcS, IdR, IdS, IeR, IeS, IfR, IfS, and the corresponding epimeric / diasteremeric mixtures are particularly preferred as herbicide A in the method of the present invention.

[0064] In the context of this invention, any ratio of malondiamide compounds of formula (I) in the corresponding epimeric / diasteremeric mixtures is considered and can be used in methods for weed control in cereal crops. Non-limiting examples of the ratio of diastereomers in the corresponding diastereomer / diastereomer mixtures are 100:0, 99.9:0.1, 99.5:0.5, 99:1, 98:2, 95:5, 90:10, 80:20, 70:30, 60:40, 55:45, 50:50, 45:55, 40:60, 30:70, 20:80, 10:90, 5:95, 2:98, 1:99, 0.5:99.5, 0.1:99.9, and 0:100. In some embodiments, the ratio of diastereomers in the corresponding diastereomer / diastereomer mixture is 95:5 or 50:50 + / - 10%.

[0065] In the context of this invention, the different ratios of diastereomer / diastereomer mixtures IaR + IaS, IbR + IbS, or IcR + IcS listed above are particularly preferred component A in the method according to the invention; in very particularly preferred diastereomer / diastereomer mixtures, the percentage of the S-diastereomer in the diastereomer / diastereomer mixture is equal to or greater than the percentage of the R-diastereomer. For example, the S-diastereomer may be 50%-100%, 60% to 100%, 70% to 100%, 80% to 100%, 90% to 100%, or 95% + / - 5%, wherein the sum of the S- and R-diastereomers is 100%.

[0066]

[0067]

[0068]

[0069] Throughout this specification and in connection with the compound or molecular portion, the prefix "C" is used. n -C m "Each indicates the range of possible carbon atoms that a molecular moiety or compound can have. The term 'C1-C'..." n "-alkyl" indicates a group of straight-chain or branched saturated hydrocarbon groups having 1 to n carbon atoms.

[0070] For example, the term "C1-C4-alkyl" refers to the group of straight-chain or branched saturated hydrocarbon groups having 1 to 4 carbon atoms. C1-C4-alkyl is methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, or tert-butyl.

[0071] The term "(C3-C6)-cycloalkyl" refers to a monocyclic saturated hydrocarbon group having 3 to 6, particularly 4 to 5, carbon ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl.

[0072] In the context of this invention, malondiamide compounds having formula (I) (herbicide A) may be used as is or in the form of their agriculturally acceptable salts. Suitable are typically salts of those cations whose cations and anions do not adversely affect the activity of the active compound, and acid addition salts of those acids.

[0073] Preferred cations are alkali metal ions, preferably lithium, sodium, and potassium ions; alkaline earth metal ions, preferably calcium and magnesium ions; and transition metal ions, preferably manganese, copper, zinc, and iron ions. Additionally, ammonium and substituted ammonium compounds in which one to four hydrogen atoms are replaced by C1-C4-alkyl, hydroxy-C1-C4-alkyl, C1-C4-alkoxy-C1-C4-alkyl, hydroxy-C1-C4-alkoxy-C1-C4-alkyl, phenyl, or benzyl groups are preferred. Specifically, ammonium, methylammonium, isopropylammonium, dimethylammonium, diethylammonium, diisopropylammonium, trimethylammonium, triethylammonium, tri(isopropyl)ammonium, heptylammonium, dodecylammonium, tetradecylammonium, tetramethylammonium, and tetraethylammonium are preferred. Salts of methylammonium, tetrabutylammonium, 2-hydroxyethylammonium (ethanolamine salt), 2-(2-hydroxyethyl-1-oxy)ethyl-1-ylammonium (diethylene glycolamine salt), di(2-hydroxyethyl-1-yl)ammonium (diethanolamine salt), tri(2-hydroxyethyl)ammonium (triethanolamine salt), tri(2-hydroxypropyl)ammonium, benzyltrimethylammonium, benzyltriethylammonium, N,N,N-trimethylethanolammonium (choline salt), as well as phosphonium ions, sulfonium ions, preferably tri(C1-C4-alkyl)sulfonium, such as trimethylsulfonium, and sulfonium oxide ions, preferably tri(C1-C4-alkyl)sulfonium oxide, and finally polyamines such as salts of N,N-bis-(3-aminopropyl)methylamine and diethylenetriamine.

[0074] The useful anions of acid addition salts are mainly chloride, bromide, fluoride, iodide, hydrogen sulfate, methyl sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and also anions of C1-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate.

[0075] In the method according to the invention, the required amount of the pure active compound (i.e., herbicide A) depends on the density of the unwanted vegetation, the developmental stage of the plant, the climatic conditions of the location where the composition is used, and the method of application.

[0076] Typically, the application rate of herbicide A is from 1 g / ha to 500 g / ha, preferably from 1 g / ha to 250 g / ha, and more preferably from 1 g / ha to 100 g / ha of active substance.

[0077] A description of a range of values ​​refers to the manner in which each individual value within that range is included in the description. This means that each individual value within the range is included in the description as if it were listed separately. The range includes endpoints, and any combination of values ​​within the range can be used independently. When referring to numeric values ​​or a range of numeric values, integers and fractions within the range are included unless the context explicitly indicates otherwise.

[0078] For example, the application rate range of 1 g / ha to 100 g / ha includes all application rates with values ​​between 1 and 100, namely 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 5 2, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 96, 97, 98, and 99, as well as values ​​such as 30.1, 35.4, 42.5, 48.8, etc.

[0079] The application rate of the herbicides mentioned above indicates the amount of active agent without adjuvants (such as carrier materials or surfactants).

[0080] In one embodiment of the method according to the invention, herbicide A is applied at an application rate of 1 g / ha to 250 g / ha, for example 2.5 g / ha to 250 g / ha, before emergence of monocotyledonous crops, particularly cereal crops.

[0081] In another embodiment of the method according to the invention, herbicide A is applied at a rate of 1 g / ha to 100 g / ha after emergence of monocotyledonous crops, particularly cereal crops.

[0082] In a specific embodiment of the method according to the invention, herbicide A is applied after emergence of monocotyledonous crops, particularly cereal crops, at an application rate of 1 g / ha to 75 g / ha, preferably 4 g / ha to 64 g / ha, and more preferably 8 g / ha to 48 g / ha.

[0083] The method or use of the present invention is particularly suitable for selectively controlling weeds, wherein herbicide A is applied to the cultivation area of ​​monocotyledonous crops, especially cereal crops, in which weeds grow or may grow.

[0084] In a preferred embodiment of the method or use of the present invention, herbicide A is applied to areas where monocotyledonous crops, particularly cereal crops, are grown.

[0085] The method or application of this invention is particularly suitable for controlling weeds in sugarcane fields and cereal crops (e.g., the following).

[0086] - Cereals (small cereal crops) such as wheat (Triticum aestivum) and wheat-like crops such as durum (T. durum), einkorn (T. monococcum), emmer (T. dicoccon), spelt (T. spelta), rye (Secale cereale), triticale (Tritiosecale), and barley (Hordeum vulgare);

[0087] - Corn (corn); Maize (Zea mays)

[0088] - Sorghum (e.g., bicolor sorghum);

[0089] - Rice (Oryza genus, such as rice and African cultivated rice).

[0090] Unless otherwise stated, herbicide A is suitable for application on any type of cereal crop as outlined herein.

[0091] In a preferred embodiment of the method according to the invention, an effective amount of herbicide A is applied to a crop cultivation area in which wheat, durum wheat, single-grain wheat, double-grain wheat, spelt wheat, rye, black wheat or barley, preferably barley or wheat, is grown.

[0092] In another preferred embodiment of the method according to the invention, an effective amount of compound (Ia) is applied to a crop cultivation area in which wheat, durum wheat, single wheat, double wheat, spelt wheat, rye, black wheat or barley, preferably barley or wheat, is grown.

[0093] In another preferred embodiment of the method according to the invention, an effective amount of compound (Ib) is applied to a crop cultivation area in which wheat, durum wheat, single wheat, double wheat, spelt wheat, rye, black wheat or barley, preferably barley or wheat, is grown.

[0094] In another preferred embodiment of the method according to the invention, an effective amount of compound (Ic) is applied to a crop cultivation area in which wheat, durum wheat, single wheat, double wheat, spelt wheat, rye, black wheat or barley, preferably barley or wheat, is grown.

[0095] The method according to the invention can be used to control a wide variety of harmful plants (undesirable vegetation), including monocotyledonous and dicotyledonous weeds, and particularly for controlling weeds selected from the genera Abutilon, Alisma, Alopecurus, and Amaranthus.*Ambrosia*, *Ammania*, *Ammi*, *Aneilema*, *Anthemis*, *Apera*, *Atriplex*, *Avena*, *Barbarea*, *Bidens*, *Brassica*, *Bromus*, *Bunias*, *Butomus*, *Capsella*, *Centaurea*, *Chenopodium* *Podium*, *Cirsium*, *Conium*, *Convolvolus*, *Cyperus*, *Datura*, *Daucus*, *Descurainia*, *Digitaria*, *Echinochloa*, *Fumaria*, *Galinsoga*, *Galium*, *Geranium*, *Helianthus*, *Heliotropium* The genera *Heteranthera*, *Hibiscus*, *Hordeum*, *Lamium*, *Leptochloa*, *Leersia*, *Lolium*, *Lycopsis*, *Matricaria*, *Mercurialis*, *Orobanche*, *Oryza*, *Panicum*, *Papaver*, *Poa*, and *Polygonum* The genera *Purslane*, *Raphanus*, *Scirpus*, *Setaria*, *Sinapis*, *Solanum*, *Sonchus*, *Sorghum*, *Sisymbrium*, *Stachys*, *Stellaria*, *Thlaspi*, *Triticum*, *Veronica*, *Viola*, and *Xanthium*.

[0096] According to one embodiment of the present invention, when the cereal crop is maize, weeds are selectively controlled, including but not limited to the following species: Abutilon theophrasti, Agropyron repens, Alopecurus myosuroides, Amaranthus hybridus, Amaranthus retroflexus, Ambrosia artemisiifolia, Ambrosia trifida, Anagallis arvensis, Anchusa officinalis, Artemisia vulgaris, Atriplex patula, Bidens pilosa, Brachiaria decumbens, Brachiaria platyphylla, Brassicanapus, and Calystegia. sepium, Capsella bursa-pastoris, Cenchrusechinatus, Chenopodium album, Chenopodium ficifolium, Chenopodium hybridum, Cirsium arvense, Convolvulus arvensis, Conyza bonariensis, Conyza canadensis, Cynodondactylon, Cyperus esculentus, Datura stramonium, Digitaria sanguinalis, Echinochloa colonum, Echinochloa crus-galli, Equisetum arvensis, Euphorbia heterophylla, Galinsogaciliata, Galinsogaciliata, Galinsogaciliata, Galium aparine, Geranium dissectum, Helianthus annuus, Ipomoeahederacea, round-leaved morning glory (Ipomoea purpurea), false cocklebur (Iva xanthiifolia), Kochia scoparia, lotus-shaped self-heal (Lamium amplexicaule), wild sesame (Lamium purpureum), unscented chamomile (Matricaria inodora), wild millet (Panicum dichotomiflorum), millet (Pennisetum glaucum), deformed grass (Phalaris paradoxa), annual bluegrass (Poa annua), knotweed (Polygonum aviculare), rolled-stem knotweed (Polygonum convolvulus), fish knotweed (Polygonum lapathifolium), spring knotweed (Polygonumpersicaria), wild radish (Raphanus raphanistrum), large foxtail grass (Setaria faberi), golden and silver yellow (Setaria glauca), thorny foxtail grass (Setaria verticillata), foxtail grass (Setaria viridis, wild mustard (Sinapis arvensis), black nightshade (Solanum nigrum), bitter sorghum (Sonchus arvensis), sweet sorghum (Sorghum bicolor, Sorghum halepense), yellow lip grass (Stachys annua), chickweed (Stellariamedia), comfrey (Symphytum officinale), thlaspi arvense, ivy speedwell (Veronica hederifolia), Arabian speedwell (Veronica persica), wild violet (Viola arvensis), cocklebur (Xanthium strumarium).

[0097] According to one embodiment of the present invention, when the cereal crop is rice, weeds are selectively controlled, including but not limited to the following species: broadleaf armgrass, tribulus terrestris, double-flowered bermudagrass, oil sedge, bald barnyard grass, awnless barnyard grass, goosegrass (Eleusine indica), white-bracted gorgonian grass, yew, golden and silver yellow, small thorn grass (Phalaris minor), large foxtail (Setaria faberi), thorny foxtail (Setaria verticillata), and cocklebur (Xanthium strumarium).

[0098] According to one embodiment of the present invention, when the cereal crop is a cereal crop, particularly barley or wheat, weeds are selectively controlled, including but not limited to the following species: *Aegilops cylindrica*, creeping icegrass, large-spike amaranth, *Anthemis arvensis*, *Apera spica-venti*, wild oats, European rapeseed, ryegrass brome (*Bromus secalinus*), sterile brome (*Bromus sterilis*), drought brome (*Bromus tectorum*), shepherd's purse, cornflower (*Centaurea cyanus*), lambsquarters, small lambsquarters, hybrid lambsquarters, silk thistle, field bindweed, fragrant grass, small tuft of grass, oilseed rape, shepherd's purse, barnyard grass, goosegrass, horsetail, and *Galeopsis*. Tetrahit, original geranium, incised geranium, Kochia scoparia, lotus-shaped selfheal, wild sesame, multiflora ryegrass (Lolium multiflorum), rigid ryegrass (Lolium rigidum), dwarf mallow (Malva neglecta), unscented magnolia, wild millet, millet, small grass, deformed grass, Kentucky bluegrass, meadow Kentucky bluegrass (Poa pratensis), knotweed, rolled stem knotweed, fish knotweed, spring knotweed, wild radish, blunt-leaved sorrel (Rumex obtusifolius), golden and silver yellow, foxtail grass, wild mustard, bitter mustard greens, sonchus asper, sonchus oleraceus, chickweed, iris, Urtica dioica, ivy speedwell, Arabian speedwell, wild violet.

[0099] According to a preferred embodiment of the present invention, when the cereal crop is maize, weeds are selectively controlled, including but not limited to the following monocotyledonous species: *Cenchrus pauciflorus*, *Chloris virgata*, *Commelina erecta*, *Bermudagrass*, *Cyperus spp.*, *Echinocloa colonum*, *Sorghum halepense*, *Trichloris crinita*, *Digitaria insularis*, *Zea mays (Volunteer)*, *Urochloa or, rachiaria decumbens*, *Tribulus terrestris*, *Commelinabenghalensis*, *Avena strigosa*, *Pennisetum americanum*, and *Panicum*. maximum), barnyard grass, broadleaf brachiaria, *Digitaria* spp., *Panicum* spp., large foxtail grass, goosegrass, stone grass, multiflora ryegrass, *Lolium* spp., *Urochloa or Brachiaria* spp., double-flowered bermudagrass, *Dactyloctenium aegyptium*, creeping grass, foxtail grass, dayflower (*Commelina communis*), *Rottboellia cochinchinensis*, *Setaria* spp., creeping icegrass (*Agropyron or Elymus repens*), creeping crabgrass (*Digitariahorizontalis*), plantain brachiaria (*Urochloa or Brachiaria plantaginea*), slender silk grass (*Leptochloa filiformis*), *Leptochloa*, *Echinochloa* spp.), Arm-shaped Grass, Bald Grass, and Spur-tailed Foxtail.

[0100] According to a preferred embodiment of the present invention, when the cereal crop is rice, weeds are selectively controlled, including but not limited to the following monocotyledonous species: dayflower, barnyardgrass (Echinochloa oryzicola, Vasing), awnless barnyardgrass, two-spike barnyardgrass (Paspalum distichum), false rice (Leersia japonica), leptochloa chinensis, field duckweed (Ischaemum rogusum), goosegrass, fine-leaved leptochloa (Leptochloa fascicularis), rice (Oryza sativa), bald barnyardgrass, creeping crabgrass, plantain (Urochloa or Brachiaria plantaginea), Lee's grass (Leerisa hexandra), leptochloa spp., broadleaf rice (Oryza latifolia), Italian early rice (Oryza sativaspontaneum), and tuftboellia. *Cochinchinensis or exaltata*, *Digitaria* spp., *Tribulus*, *Luziola subintegra*, *Commelina diffusa*, *Chloris* spp., *Leptochloa filiformis*, *Echinochloacrus-pavonis*, *Cynodon dactylon*, *Tribulus*, *Bermudagrass*, *Tricholoma matsudana*, *Digitaria rubra*, *Leptochloapanicoides*, *Panicum dichotomiflorum*, *Paspalum* spp., and wild rice.

[0101] According to a preferred embodiment of the invention, when the cereal crop is a cereal crop, particularly barley or wheat, weeds are selectively controlled, including but not limited to the following monocotyledonous species: Japanese wild oat (Alopecurus japonicus Steud), wild oat (Alopecurus aequalis Sobol), large-spike wild oat, parsnip, Avena spp., wild oat (Avena fatua L.), unfurled wild oat (Avenasterillis), bromegrass (Bromus japonicus Thunb.), jointed goatgrass (Aegilops tauschii Coss.), jointed goatgrass, Sclerochloa kengiana (Ohwi) Tzvel., Beckmannia syzigachne (Steud.) Fernald, ryegrass (Lolium spp.), multiflora ryegrass (Lolium multiflorum Lam.), and Kentucky bluegrass (Poa trivialis). L.), Ploypogon fugax. N., Phleumpaniculatum, Puccinellia distans, Lolium rigidum, Echinochloa crus-galli, Urochloa panicoides, Bromus spp., Poa spp., Hordeum leporinum, Phalaris spp., Phalaris minor, Poa annua, Agrostis alba, creeping icegrass, creeping crabgrass, Lolium perenne, Phragmites australia, Imperata cylindrica, Bermuda grass, Bromus spp. tectorum), Poa spp, Phalaris brachystachys, Setaria glauca or pumila, Setaria viridis, Phalaris persicaria, Lolium persicum, Agropyron or Elymus repens, Hordeum jubatum, and Secale cereale.

[0102] According to a highly preferred embodiment of the invention, when the cereal crop is a cereal crop, particularly barley or wheat, the following monocotyledonous weed genera are selectively controlled: *Alopecurus*, *Apis*, *Oat*, *Hymenopterus*, *Broomgrass*, *Commelina*, *Digitaria*, *Barnyardgrass*, *Lolium*, *Poa*, and *Setaria*.

[0103] Compositions containing herbicide (A) can generally be applied to weeds at any growth stage with good results. In one embodiment, application of the composition containing herbicide (A) up to the BBCH growth stage 37 of the weeds showed effective weed control. In a preferred embodiment, application of the composition containing herbicide (A) up to the BBCH growth stage 32 of the weeds showed effective weed control.

[0104] In the method according to the invention for selectively controlling weeds in cereal crops, the composition containing herbicide (A) can generally be applied after crop emergence.

[0105] In one embodiment, the composition containing herbicide (A) is applied after crop emergence until BBCH growth stage 37.

[0106] In one embodiment, the composition comprising herbicide (A) is applied at BBCH growth stage 12 to 32 after crop emergence.

[0107] In another embodiment, the composition comprising herbicide (A) is applied after crop emergence at BBCH growth stages 13 to 29, for example, BBCH growth stages 14 to 21.

[0108] In a highly preferred embodiment, the composition comprising herbicide (A) is applied when both the monocotyledonous crop plants and weeds have emerged from the soil, for example, after emergence at BBCH growth stage 12 to 32 of the crop.

[0109] An exemplary method according to the present invention is described by the following embodiments:

[0110] M.1: A method for selectively controlling weeds in cereal crops, the method comprising applying an effective amount of herbicide A to a crop cultivation area, the herbicide being selected from compounds having formula (I) and salts of compounds having formula (I).

[0111] ;

[0112] Wherein R is hydrogen, (C1-C3)-alkyl or (C3-C5)-cycloalkyl; and wherein herbicide A is applied after emergence of cereal crops at an application rate of 1 g / ha to 100 g / ha, preferably at an application rate of 8 g / ha to 64 g / ha; and wherein no safener is applied.

[0113] M.2: A method for selectively controlling weeds in cereal crops, the method comprising applying an effective amount of herbicide A to a crop cultivation area, the herbicide being selected from compounds having formula (I) and salts of compounds having formula (I).

[0114] ;

[0115] Wherein R is hydrogen, (C1-C3)-alkyl or (C3-C5)-cycloalkyl; and wherein herbicide A is applied at a rate of 1 g / ha to 100 g / ha, preferably 8 g / ha to 64 g / ha, after emergence of cereal crops and weeds; and wherein no safener is applied.

[0116] M.3: A method for selectively controlling monocotyledonous weeds in cereal crops, the method comprising applying an effective amount of herbicide A to a crop cultivation area, the herbicide being selected from compounds having formula (I) and salts of compounds having formula (I).

[0117] ;

[0118] Wherein R is hydrogen, (C1-C3)-alkyl or (C3-C5)-cycloalkyl; and wherein herbicide A is applied after emergence of cereal crops at an application rate of 1 g / ha to 100 g / ha, preferably at an application rate of 8 g / ha to 64 g / ha; and wherein no safener is applied.

[0119] M.4: A method for selectively controlling monocotyledonous weeds in cereal crops, the method comprising applying an effective amount of herbicide A to a crop cultivation area, the herbicide being selected from compounds having formula (I) and salts of compounds having formula (I).

[0120] ;

[0121] Wherein R is hydrogen, (C1-C3)-alkyl or (C3-C5)-cycloalkyl; and wherein herbicide A is applied at a rate of 1 g / ha to 100 g / ha, preferably 8 g / ha to 64 g / ha, after emergence of cereal crops and monocotyledonous weeds; and wherein no safener is applied.

[0122] The composition of herbicide A can be applied in a conventional manner using techniques familiar to the technician. Suitable techniques include spraying, atomizing, dusting, broadcasting, or watering. The type of application, in a well-known manner, depends on the intended purpose; in any case, it should ensure the finest possible distribution of the active ingredient.

[0123] Compositions of herbicide A are applied to areas primarily by spraying, particularly by foliar spraying, using an aqueous dilution of the active ingredient. Application can be carried out using conventional spraying techniques, for example, water as a carrier and a spray rate of approximately 10 to 2000 l / ha or 50 to 1000 l / ha, for example, 100 to 500 l / ha. Application of compositions of herbicide A via low-volume and ultra-low-volume methods is possible, as is their application in particulate form.

[0124] If certain crop plants are poorly tolerant of the active ingredient, the application technique of herbicide A composition can be used, which involves spraying the herbicide A composition in a manner that minimizes contact (if any) with the leaves of the sensitive crop plants while reaching the leaves of unwanted plants growing below or the bare soil (post-directed, final field application).

[0125] When the composition of herbicide A is used in a sterilization process, it can be applied before crop sowing (or planting) or after sowing but before crop emergence.

[0126] In addition to the active ingredient or composition, the agrochemical composition of herbicide A and the formulation of herbicide A also contain at least one organic or inorganic carrier material. The formulation may also contain, if desired, one or more surfactants and, if desired, one or more other adjuvants commonly used in crop protection compositions.

[0127] In the formulation, the active ingredient and optional other active ingredients are present in suspension, emulsion, or dissolved form. The formulation may be in the form of aqueous solution, powder, suspension, as well as highly concentrated aqueous, oil or other suspensions or dispersions, water emulsions, water microemulsions, water suspension emulsions, oil dispersions, pastes, dusts, spreading materials, or granules.

[0128] Depending on the type of formulation, they contain one or more liquid or solid carriers, (if appropriate) surfactants (such as dispersants, protective colloids, emulsifiers, wetting agents, and thickeners), and (if appropriate) other adjuvants commonly used in formulating product protection products. Those skilled in the art are well familiar with the formulation of such formulations. Other adjuvants include, for example, organic and inorganic thickeners, bactericides, antifreeze agents, defoamers, colorants, and binders for seed formulations.

[0129] Suitable carriers include liquid and solid carriers. Liquid carriers include, for example, non-aqueous solvents such as cyclic and aromatic hydrocarbons, such as paraffin, tetrahydronaphthalene, alkylnaphthalene and their derivatives, alkylbenzene and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, strongly polar solvents such as amines such as N-methylpyrrolidone, and water, and mixtures thereof. Solid carriers include, for example, minerals such as silica, silica gel, silicates, talc, kaolin, limestone, lime, chalk, red basalt, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, and plant-derived products such as grain flour, bark flour, wood flour and nut shell powder, cellulose powder, or other solid carriers.

[0130] Suitable surfactants (auxiliaries, wetting agents, thickeners, dispersants, and emulsifiers) are aromatic sulfonic acids, such as lignin sulfonic acids (e.g., Borrespers type, Borregard), phenol sulfonic acids, naphthalene sulfonic acids (Morwet type, Akzo Nobel), and dibutylnaphthalene sulfonic acids (Nekal type, BASF). Alkali metal salts, alkaline earth metal salts, and ammonium salts of fatty acids, alkyl sulfonates and alkyl aryl sulfonates, alkyl sulfates, lauryl ether sulfates, and fatty alcohol sulfates, and salts of sulfated hexa-, hepta-, and octadecyl alcohols, as well as salts of fatty alcohol glycol ethers, condensates of sulfonated naphthalene and its derivatives with formaldehyde, condensates of naphthalene or naphthalene sulfonic acid with phenol and formaldehyde, octylphenol polyoxyethylene ethers, ethoxylated isooctyl-, octyl-, or nonylphenol, alkylphenyl or tributylphenyl polyethylene glycol ethers, alkyl aryl polyether alcohols, isotriadecyl alcohol, fatty alcohol / ethylene oxide condensates Materials, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, lauryl glycol ether acetate, sorbitol esters, lignin sulfite waste liquid and proteins, denatured proteins, polysaccharides (e.g., methylcellulose), hydrophobically modified starch, polyvinyl alcohol (Mowiol type, Clariant), polycarboxylate (BASF, Sokalan type), polyalkoxylates, polyvinylamine (BASF, Lupamine type), polyethyleneimine (BASF, Lupasol type), polyvinylpyrrolidone and its copolymers.

[0131] Examples of thickeners (i.e., compounds that impart improved flow properties to formulations, i.e., compounds that have high viscosity at rest and low viscosity when in motion) are polysaccharides, such as xanthan gum (Kelzan® from Kelco), Rhodopol® 23 (Rhone Poulenc) or Veegum® (from RTVanderbilt) as well as organic and inorganic platy minerals, such as Attaclay® (from Engelhardt)

[0132] Examples of defoamers are silicone emulsions (such as Silikon). ® SRE, Wacker or Rhodorsil®, from Rhodia, long-chain alcohols, fatty acids, fatty acid salts, organofluorine compounds and mixtures thereof.

[0133] Fungicides can be added to stabilize water-based herbicidal formulations. Examples of fungicides include dichlorophenol and benzyl alcohol hemiformal-based fungicides (Proxel® from ICI, Acticide® RS from Thor Chemie, and Kathon® MK from Rohm & Haas), as well as isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones (Acticide MBS from Thor Chemie).

[0134] Examples of antifreeze agents are ethylene glycol, propylene glycol, urea, or glycerin.

[0135] Examples of colorants are both slightly water-soluble pigments and water-soluble dyes. Examples that may be mentioned are dyes known by the following names: Rhodamine B, CI Pigment Red 112 and CI Solvent Red 1, as well as Pigment Blue 15:4, Pigment Blue 15:3, Pigment Blue 15:2, Pigment Blue 15:1, Pigment Blue 80, Pigment Yellow 1, Pigment Yellow 13, Pigment Red 112, Pigment Red 48:2, Pigment Red 48:1, Pigment Red 57:1, Pigment Red 53:1, Pigment Orange 43, Pigment Orange 34, Pigment Orange 5, Pigment Green 36, Pigment Green 7, Pigment White 6, Pigment Brown 25, Basic Violet 10, Basic Violet 49, Acid Red 51, Acid Red 52, Acid Red 14, Acid Blue 9, Acid Yellow 23, Basic Red 10, Basic Red 108.

[0136] Examples of adhesives are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, and methylcellulose (tylose).

[0137] To prepare emulsions, pastes, or oil dispersions, the active ingredient (either as is or dissolved in oil or solvent) can be homogenized in water using a wetting agent, thickener, dispersant, or emulsifier. Alternatively, concentrates consisting of the active substance, wetting agent, thickener, dispersant, or emulsifier, and (if desired) solvent or oil can be prepared, and these concentrates are suitable for dilution with water.

[0138] Powders, spreading materials, and dusts can be prepared by mixing or simultaneously grinding the active ingredients herbicides A and B with a solid carrier.

[0139] Granules, such as coated granules, impregnated granules, and uniform granules, can be prepared by bonding the active ingredient to a solid carrier.

[0140] It may be beneficial to apply herbicide A alone or in combination with other herbicides, or additionally in mixtures with other crop protectants, such as with agents used to control harmful organisms or plant pathogenic fungi or bacteria. Also of interest is its miscibility with mineral salt solutions used to treat nutrient and trace element deficiencies. Other additives such as non-phytotoxic oils and oil concentrates may also be added.

[0141] These formulations contain an effective amount of herbicide A. The concentration of the active ingredient in the formulation can vary over a wide range. Typically, the formulation contains 1% to 98%, preferably 10% to 60% by weight, of the active ingredient (herbicide A and optional other active ingredients). The active ingredient is used at a purity of 90% to 100%, preferably 95% to 100% (based on NMR spectra).

[0142] Herbicide A (i.e., the active compound or composition) can be formulated, for example, as follows:

[0143] Products diluted with water

[0144] A water-soluble concentrate

[0145] Dissolve 10 parts by weight of the active compound (or composition) in 90 parts by weight of water or a water-soluble solvent. Alternatively, add a wetting agent or other adjuvant. The active compound dissolves upon dilution with water. This yields a formulation containing 10% active compound by weight.

[0146] B Dispersible Concentrate

[0147] Dissolve 20 parts by weight of the active compound (or composition) in 70 parts by weight of cyclohexanone, and add 10 parts by weight of a dispersant, such as polyvinylpyrrolidone. Dilute with water to obtain a dispersion. The active compound content is 20% by weight.

[0148] C emulsifiable concentrate

[0149] Dissolve 15 parts by weight of the active compound (or composition) in 75 parts by weight of an organic solvent (e.g., an alkyl aromatic compound), and add calcium dodecylbenzenesulfonate and castor oil ethoxylate (5 parts by weight in each case). Dilute with water to obtain an emulsion. The formulation has an active compound content of 15% by weight.

[0150] D Emulsion

[0151] 25 parts by weight of the active compound (or composition) are dissolved in 35 parts by weight of an organic solvent (e.g., an alkyl aromatic compound), and calcium dodecylbenzenesulfonate and castor oil ethoxylate (5 parts by weight in each case) are added. This mixture is introduced into 30 parts by weight of water using an emulsifier (Ultraturrax) to form a homogeneous emulsion. The emulsion is diluted with water. The formulation has an active compound content of 25% by weight.

[0152] E suspension

[0153] In a stirred ball mill, 20 parts by weight of the active compound (or composition) are pulverized, and 10 parts by weight of a dispersant and wetting agent, along with 70 parts by weight of water or an organic solvent, are added to obtain a fine suspension of the active compound. The suspension is then diluted with water to obtain a stable suspension of the active compound. The active compound content in the formulation is 20% by weight.

[0154] F Water-dispersible granules and water-soluble granules

[0155] 50 parts by weight of the active compound (or composition) are finely ground and 50 parts by weight of a dispersant and a wetting agent are added. The mixture is then processed into water-dispersible or water-soluble granules using advanced equipment such as extrusion, spray towers, or fluidized beds. The granules are diluted with water to obtain a stable dispersion or solution of the active compound. The formulation contains 50% active compound by weight.

[0156] G water-dispersible powder and water-soluble powder

[0157] 75 parts by weight of the active compound (or composition) are milled in a rotor-stator mill, and 25 parts by weight of a dispersant, wetting agent, and silica gel are added. The mixture is diluted with water to obtain a stable dispersion or solution of the active compound. The active compound content of the formulation is 75% by weight.

[0158] H gel formulation

[0159] 20 parts by weight of the active compound (or composition), 10 parts by weight of the dispersant, 1 part by weight of the gelling agent, and 70 parts by weight of water or organic solvent are mixed in a ball mill to obtain a fine suspension. The suspension is then diluted with water to obtain a stable suspension containing 20% ​​by weight of the active compound.

[0160] Aqueous forms can be prepared by adding water from emulsion concentrates, suspensions, pastes, wettable powders, or water-dispersible granules.

[0161] Examples of uses

[0162] Biological examples

[0163] The herbicidal activity of compounds having formula (I) was confirmed by the following greenhouse experiments:

[0164] The culture containers used were plastic flowerpots containing sandy loam soil with approximately 3.0% organic matter as a substrate. Seeds of test plants were sown individually for each species.

[0165] For pre-emergence treatment, after sowing, the active ingredient, already suspended or emulsified in water, is applied directly using a fine-dispensing nozzle. The containers are gently irrigated to promote germination and growth, and then covered with a transparent plastic cover until the test plants have rooted. This covering ensures uniform germination of the test plants, unless they have been damaged by the active ingredient.

[0166] For post-emergence treatment, depending on the plant's habits, test plants are first allowed to grow to a height of 3 to 20 cm, and then treated only with the active ingredient suspended or emulsified in water. For this purpose, test plants are either directly sown and grown in the same container, or they are first grown individually as seedlings and then transplanted into test containers a few days before treatment.

[0167] Depending on the species, the test plants were kept at 10°C-25°C or 20°C-35°C, respectively.

[0168] The testing period lasts 2 to 4 weeks. During this time, the test plants are cared for, and their responses to individual treatments are evaluated.

[0169] Evaluations were conducted using a scale of 0 to 100. 100 indicates no plant emergence, or at least complete destruction of the above-ground portion, while 0 indicates no damage or normal growth. Values ​​of 70 to < 90 were given for good herbicidal activity, and values ​​of 90 to 100 were given for very good herbicidal activity.

[0170] The test plants used in the greenhouse experiment belong to the following species:

[0171] EPPO code scientific name

[0172] Abutilon

[0173] ALOMY Big Ear Sees Wheat Maiden

[0174] AMARE Amaranthus retroflexata

[0175] APESV Apila Grass

[0176] AVEFA Wild Oats

[0177] BRADC (Brachiaria decumbens)

[0178] BROSE Rye-like Broccoli

[0179] BRSNS rapeseed (spring)

[0180] COMBE rice bag grass (Commelina benghalensis)

[0181] DIGSA Ma Tang

[0182] ECHCG barnyard grass

[0183] GALAP (Galium aparine)

[0184] Geranium pusillum (GERPU)

[0185] GLXMA bean

[0186] HORVS Barley (Spring Barley)

[0187] HORVW Barley (Winter Barley)

[0188] LOLMU Multiflora Ryegrass

[0189] MATIN Unscented Matricaria

[0190] ORYSA rice

[0191] PAPRH Poppy

[0192] POAAN Kentucky Bluegrass

[0193] POLAV flat knotweed

[0194] POLCO Polygonum cuspidatum

[0195] RAPRA Wild Radish

[0196] SEBEX Sesbania exaltata

[0197] SETFA giant foxtail

[0198] SETVI foxtail grass

[0199] SINAR Wild Mustard Greens

[0200] STEME (Steel)

[0201] THLAR

[0202] TRZAS wheat (spring wheat)

[0203] TRZAW wheat (winter wheat)

[0204] VERPE Arabian Veronica

[0205] ZEAMX Corn

[0206] The invention will be described in more detail by way of examples below.

[0207] legend:

[0208] • Application rate [g / ha]

[0209] •DAT: Number of days after processing

[0210] •GS: BBCH growth stage

[0211] • Compound Ib ;IbR + IbS (approximately 50:50), 5% [w / v]

[0212] • Compound Ib ;IbR + IbS (approx. 5:95), 5% [w / v]

[0213] • Compound Ia; IaR + IaS (approximately 50:50), 5% [w / v]

[0214] • Compound Ic; IcR + IcS (approximately 50:50), 5% [w / v]

[0215] • Compound Id; IdR + IdS (approximately 50:50), 5% [w / v]

[0216] • Compound Ie; IeR + IeS (approximately 50:50), 5% [w / v]

[0217] • Compound If; IfR + IfS (approximately 50:50), 5% [w / v]

[0218] • Compound II.1, 5% [w / v]

[0219] • Compound II.2, 5% [w / v]

[0220] • Compound II.3, 5% [w / v]

[0221] • Compound III.1, 5% [w / v]

[0222] • Compound III.2, 5% [w / v]

[0223] • Compound V.1, 5% [w / v]

[0224] • Compound VI.1, 5% [w / v]

[0225] • Compound VI.2, 5% [w / v]

[0226] • Compound VII.1, 5% [w / v]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234] .

Claims

1. A method for selectively controlling weeds in monocotyledonous crops, the method comprising applying an effective amount of herbicide A to a crop cultivation area, the herbicide being selected from compounds having formula (I) and salts of compounds having formula (I). ； in, R is hydrogen, (C1-C6)-alkyl, or (C3-C6)-cycloalkyl.

2. The method as described in claim 1, wherein, Do not use safety agents.

3. The method as described in claim 1 or 2, wherein, This monocotyledonous crop is a cereal crop selected from grains, corn, sorghum, and rice.

4. The method of claim 3, wherein, The monocotyledonous crop is selected from the following cereal crops: wheat, durum wheat, single wheat, double wheat, spelt wheat, rye, triticale and barley, preferably barley or wheat.

5. The method according to any one of claims 1 to 4, wherein, The weed is a monocotyledonous weed.

6. The method of claim 5, wherein, The weeds are selected from the following monocotyledonous weeds: Alopecurus, Apila, Oat, Armillaria, Bromus, Commelina, Digitaria, Barnyardgrass, Ryegrass, Poa, and Setaria.

7. The method according to any one of claims 1 to 6, wherein, Herbicide A is applied before the crop emerges.

8. The method according to any one of claims 1 to 6, wherein, Herbicide A is applied after the crop has emerged.

9. The method according to any one of claims 1 to 6, wherein, Herbicide A is applied after the crop and the weed have emerged.

10. The method according to any one of claims 1 to 9, wherein, The herbicide A may be applied once, twice, or three times until the crop is harvested, preferably once until the crop is harvested.

11. The method according to any one of claims 1 to 10, wherein, The herbicide A is selected from the compounds having formula (I) according to claim 1, and R is hydrogen, (C1-C3)-alkyl or (C3-C5)-cycloalkyl.

12. The method according to any one of claims 1 to 10, wherein, The herbicide A is selected from the compounds having formula (I) according to claim 1, and R is hydrogen, methyl, ethyl, isopropyl, cyclopropyl, or cyclobutyl, preferably hydrogen, methyl, or isopropyl.

13. A composition comprising herbicide A according to claim 1, 11 or 12 and at least one adjuvant commonly used in the formulation of crop protection compounds.

14. The composition of claim 13, wherein the composition comprises an additional herbicide.

15. The use of herbicide A according to claim 1, 11 or 12 or the composition according to claim 13 or 14 for selectively controlling weeds selected from monocotyledonous crops such as cereals, corn, sorghum and rice.

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