Fungus-based biocides

Abstract

The present invention relates to the use of a compound according to formula (I) of the present application or a salt thereof as a herbicide, and to corresponding methods for controlling weeds.

Description

[0001]Fungal-based biocides. The present invention relates to the use of a compound of formula (I) of the present application or a salt thereof as a herbicide, as well as to corresponding methods for controlling weeds. The use of secondary fungal metabolites from necrotizing plant-pathogenic fungi is an innovative approach to developing new herbicides with novel modes of action. The enormous structural diversity of fungal secondary metabolites and, above all, their high efficacy make phytotoxins from necrotizing fungi attractive as a new source of herbicides. Furthermore, new fungal metabolites can have novel modes of action not covered by synthetic herbicides. Furthermore, the fungal metabolites can address multiple targets simultaneously, which reduces the risk of resistance development.Given this rich reservoir of putative herbicides, it is surprising that no product based on fungal molecules has yet been commercialized. The present invention is therefore based on the object of providing novel herbicides based on secondary fungal metabolites from necrotizing plant-pathogenic fungi. This object is achieved by the embodiments characterized in the claims. In particular, the invention provides the use of a compound according to formula (I) of the present application as a herbicide, as well as corresponding methods for controlling weeds. Accordingly, the present invention relates to the use of a compound according to formula (I) or a salt thereof as a herbicide: wherein R. 1is selected from the group consisting of (i) an unsubstituted (C2-C12) alkyl alcohol, (ii) an unsubstituted (C2-C12) alkenyl alcohol, and (iii) an unsubstituted (C2-C12) alkynyl alcohol; R 2 , R 3 , R 4 , R 5 and R 6 are each independently selected from the group consisting of hydrogen (H), halogen (F, Cl, Br, I), hydroxyl (OH), a linear or branched (C1-C6)-alkyl, a linear or branched O-(C1-C6)-alkyl, a (C3-C6)-cycloalkyl, and a (C3-C6)-cycloalkoxy; and m is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10. The term "herbicide" as used here refers to weed control agents, i.e. substances that kill unwanted plants. The compounds or salts thereof used according to the invention can preferably be used as total herbicides that are effective against very many plants. The group R 1in the compounds of formula (I) according to the invention or salts thereof is selected from the group consisting of (i) an unsubstituted (C2-C12) alkyl alcohol, (ii) an unsubstituted (C2-C12) alkenyl alcohol, and (iii) an unsubstituted (C2-C12) alkynyl alcohol; preferably from the group consisting of (i) an unsubstituted (C2-C8) alkyl alcohol, (ii) an unsubstituted (C2-C8) alkenyl alcohol, and (iii) an unsubstituted (C2-C8) alkynyl alcohol. In further preferred embodiments, the group R 1 an unsubstituted (C2-C8) alkyl alcohol. In further preferred embodiments, the group R 1 an unsubstituted (C5-C7) alkyl alcohol, or an unsubstituted (C2-C4) alkyl alcohol. In preferred embodiments, the groups R 2 , R 3 , R 4 , R 5 and R 6in the compounds of formula (I) according to the invention or salts thereof are each independently selected from the group consisting of hydrogen (H), halogen (F, Cl, Br, I), a linear or branched (C1-C4)-alkyl, hydroxyl (OH), a linear or branched O-(C1-C4)-alkyl, a (C3-C6)-cycloalkyl, and a (C3-C6)-cycloalkoxy. In this context, the linear or branched (C1-C4)-alkyl is preferably selected from the group consisting of methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl and tert-butyl, with tert-butyl being particularly preferred. Furthermore, the linear or branched O-(C1-C6)-alkyl is preferably selected from the group consisting of methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy and tert-butoxy. The (C3-C6)-cycloalkyl is preferably selected from cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl, with cyclohexyl being particularly preferred.Finally, the (C3-C6)-cycloalkoxy is preferably selected from cyclopropoxy, cyclobutoxy, cyclopentoxy, and cyclohexoxy. In a preferred embodiment, one of the groups R is 2 , R 3 , R 4 , R 5 and R 6 in the compounds according to the invention according to formula (I) or salts thereof tert-butyl, and the remaining groups R 2 , R 3 , R 4 , R 5 and R 6 H. R is preferred 4 , R 5 or R 6 , more preferably R 4 , tert-butyl. Furthermore, (i) m is preferably 0, and / or (ii) R 1 an unsubstituted (C5-C7) alkyl alcohol. In a further preferred embodiment, one of the groups R 2 , R 3 , R 4 , R 5 and R 6 in the compounds according to the invention of formula (I) or salts thereof cyclohexyl, and the remaining groups R 2 , R 3 , R 4 , R 5 and R6 H. R is preferred 4 Cyclohexyl. Further preferably (i) m is 0, and / or (ii) R 1 an unsubstituted (C2-C4) alkyl alcohol. In further preferred embodiments, the groups R 2 , R 3 , R 4 , R 5 and R 6 in the compounds of formula (I) according to the invention or salts thereof, each represents hydrogen (H). Furthermore, in preferred embodiments, m in the compounds of formula (I) according to the invention or salts thereof is 0. In a specific and preferred embodiment, the compound of formula (I) used in the invention is 4-(tert-butyl)-N-(5-hydroxypentyl)benzenesulfonamide according to the formula (2) below, or a salt thereof. In a further specific and preferred embodiment, the compound of formula (I) used according to the invention is 3-(tert-butyl)-N-(5-hydroxypentyl)benzenesulfonamide according to the formula (10) below, or a salt thereof. In a further specific and preferred embodiment, the compound of formula (I) used according to the invention is N-(4-hydroxybutyl)benzenesulfonamide according to the formula (1a) below, or a salt thereof. In the present invention, N-(4-hydroxybutyl)-benzenesulfonamide was isolated as natural product 1 from liquid cultures of Colletotrichum graminicola (teleomorph Glomerella graminicola), which is an important phytopathogenic fungus from the group of Ascomycetes and causes anthracnose in maize, but also in other cereals and grasses.In further specific embodiments, the compound of formula (I) used according to the invention is selected from the group consisting of 4-(tert-butyl)-N-(2-hydroxyethyl)benzenesulfonamide (compound (3)), 4-(tert-butyl)-N-(3-hydroxypropyl)benzenesulfonamide (compound (4)), 4-(tert-butyl)-N-(4-hydroxybutyl)benzenesulfonamide (compound (5)), N-(6-hydroxyhexyl)-4-methylbenzenesulfonamide (compound (6)), 3-(tert-butyl)-N-(2-hydroxyethyl)benzenesulfonamide (compound (7)), 3-(tert-butyl)-N-(3-hydroxypropyl)benzenesulfonamide (compound (8)), 3-(tert-butyl)-N-(4-hydroxybutyl)benzenesulfonamide (compound (9)), and 4-cyclohexyl-N-(2-hydroxyethyl)benzenesulfonamide (Compound (11)). According to the present invention, the compounds of formula (I) can also be present as salts. Suitable salts or counterions are not subject to any particular restrictions and include, for example, sodium, potassium, calcium, and magnesium salts of the respective compounds.The compounds of formula (I) or salts thereof used according to the invention are preferably used as a herbicide (or total herbicide) for controlling weeds from the class of Angiospermae (flowering plants), more preferably from the Dicotyledons (dicotyledons) or Monocotyledons (monocotyledons). The present invention further relates to a method for controlling one or more weeds, comprising applying an effective amount of a compound of formula (I) or a salt thereof, as defined above for use according to the invention, to a plant or parts of a plant. The term "weed" as used here refers to any unwanted plants of the spontaneous accompanying vegetation in crop stands, grassland, or gardens that are not deliberately cultivated there and develop from the seed potential of the soil, via root runners, or via seed migration.The weed to be controlled according to the invention is preferably one or more plants from the class of Angiosperms (flowering plants), more preferably from the Dicotyledons (dicotyledons) or Monocotyledons (monocotyledons). The plant to which an effective amount of a compound of formula (I) or a salt thereof is applied according to the invention is the weed to be controlled according to the invention. The method according to the invention for controlling one or more weeds can be used preventively or curatively, i.e. the compound of formula (I) or the salt thereof can be used as a pre-emergence herbicide or as a post-emergence herbicide. Methods for applying an effective amount of a compound of formula (I) or a salt thereof to a plant or parts of a plant are not subject to any particular restrictions and are known in the prior art.These include, for example, spraying, misting, painting, or immersing the plant. The compound of formula (I) or the salt thereof can be applied, for example, as a hydraulic spray of high liquid volumes, as a hydraulic spray of low liquid volumes, as an ultra-low-volume spray, by high-pressure liquid injection, by gap injection, as a forced air spray, as an air spray, or as dust. The uptake of the compound of formula (I) or the salt thereof preferably occurs via the leaves of the plant. The compound of formula (I) or the salt thereof used in the process according to the invention is preferably present in a solution, for example in an aqueous solution and / or in an organic solvent, wherein the concentration of the compound of formula (I) or the salt thereof in the solution is in the range from 1 µM to 10 mM, preferably from 100 µM to 5 mM, particularly preferably about 2 mM.Accordingly, the effective amount of the compound of formula (I) or the salt thereof applied according to the invention is an amount in which the compound of formula (I) or the salt thereof is present in the stated concentrations after application to the plant. In preferred embodiments, the compound of formula (I) or the salt thereof is in the form of a carrier composition mixture, i.e. in a composition comprising at least one carrier substance and the compound of formula (I) or the salt thereof, wherein the compound of formula (I) or the salt thereof is present in an amount of 0.001 to 99% by weight, preferably 0.001 to 75% by weight, based on the total weight of the carrier composition mixture. Furthermore, carrier composition mixtures for direct application or field application can contain the compound of formula (I) or the salt thereof in an amount between 0.001 and 5% by weight, preferably between 0.01 and 3% by weight.-%, based on the total weight of the carrier composition mixture. Corresponding carrier composition mixtures are not subject to any particular restrictions and are known in the art. Preferably, a carrier composition mixture comprises one or more dispersible, inert carriers. These can comprise one or more dispersible, inert carrier solids and / or one or more dispersible, inert carrier liquids, for example, an inert organic solvent and / or water. In certain embodiments, the carrier composition mixture further comprises one or more surface-active carrier adjuvants. The term "about" as used herein represents a modifier of the specified value of ± 10%, preferably ± 9%, ± 8%, ± 7%, ± 6%, ± 5%, ± 4%, ± 3%, ± 2%, ± 1.5%, ± 1% or ± 0.5%. Thus, for example, the phrase "about 100" denotes a range of values ​​from 90 to 110.The figures show: Figure 1: Efficacy test using a leaf spot bioassay after 72 hours of exposure. Natural product (1): N-(4-hydroxybutyl)benzenesulfonamide isolated from liquid cultures of Colletotrichum graminicola; Compound (2): Synthetically produced 4-(tert-butyl)-N-(5-hydroxypentyl)benzenesulfonamide. Figure 2: Efficacy test on A. thaliana (A) and S. cereale (B) using a leaf disc assay (compounds (2) and (10)). Figure 3: Efficacy test of compound (2) using a whole plant test on Nicotiana benthamiana (plant age 30 days). The present invention is further illustrated by the following non-limiting examples. Examples Materials and Methods: General. All reagents and solvents were of analytical grade or purified using standard methods. Reactions were monitored by thin-layer chromatography on silica gel 60 F254 (Merck, 0.040-0.063 mm) and detected with UV light (λ = 254 nm and λ = 366 nm).Solutions were concentrated at 40°C under reduced pressure. NMR. The NMR spectra were recorded using an Agilent DD2400 MHz NMR spectrometer. The solvent used for the samples was either deuterated methanol (CD3OD) or deuterated dimethyl sulfoxide (DMSO-d6) with 0.03% TMS as an internal standard. The UHPLC-HRESIMS spectra and the collision-induced dissociation (CID) mass spectra were recorded in positive ion mode using an Orbitrap Q Exactive Plus (Thermofisher Scientific).The sample solutions were previously separated by chromatography (column: Thermo Scientific BEH C18 (length: 5 cm; diameter: 2.1 mm; pore size: 130 Å; particle size: 1.7 µM; column temperature: 40 °C; injection volume: 2 µL; mobile phase: A: H2O + 0.1% formic acid, B: acetonitrile + 0.1% formic acid; flow rate: 0.3 ml / min; gradient (A:B): 95:5 (0.5 min) in 10 min to 2:98 (5 min)) and detected using a photodiode array detector (PDA, Thermo Scientific) at λ = 190-240 nm. Ionization was performed using electrospray ionization (HESI ion source; spray voltage 4.0 kV; nebulizing and auxiliary gas: nitrogen; evaporation temperature: 250 °C; capillary temperature: 275 °C, FTMS resolution Full MS 30000; MS. n15000). The CID mass spectra were recorded with normalized collision energies (NCE) of 35–50%. The mass spectrometer was calibrated externally (Pierce® LTQ Velos ESI positive ion calibration solution, Thermofisher Scientific). Alternatively, an Expression LA CMS (compact mass spectrometer, Advion, Ithaca, USA) system was used, which was equipped with an ESI ion source (negative and positive mode) or an APCI ion source (negative and positive mode): Parameters: capillary temperature: 200 / 250 °C, source voltage offset: 15 / 20 V, source voltage dynamic: 10 / 20 V, source gas temperature: 200 / 350 °C, MS scan range m / z 100–600. Data acquisition and processing were performed using the Mass Express program (Advion). IR spectra: IR spectra were recorded with a Spectrum 1000 FT-IR spectrometer from Perkin Elmer (Rodgau, Germany). The UV / Vis spectra were recorded with a Lambda 14 spectrometer from Perkin Elmer (Rodgau, Germany). Melting points (mp) were determined using a Leica hot-stage microscope Galen III (Leica Biosystems, Nussloch, Germany) and are uncorrected.Microanalyses were performed using an Elementar Vario EL (CHNS) instrument (Elementar Analysensysteme GmbH, Elementar-Straße 1, D-63505, Langenselbold, Germany). Column chromatography. Column chromatographic separations were performed on silica gel 60 (Merck, 0.063–0.200 mm), silanized silica gel 60 (0.063–0.200 mm, Merck, Germany), and polyamide SC 6-Ac (Macherey-Nagel, Germany). Culture conditions. Colletotrichum graminicola (strain M1.001) was cultured using the emergence method with cotton wool and the liquid medium CM (Complete Medium) consisting of 10 g glucose, 1 g Ca(NO3)2, 1 g yeast extract, 1 g casein hydrolysate, 0.2 g KH2PO4, 0.25 g MgSO4, and 0.05 g NaCl to 1 L distilled water. For this purpose, 100 Erlenmeyer flasks (1 L) were filled with 4 g of cotton wool and 200 ml of CM medium. The cotton wool was filled with a 1 cm diameter. 2Large pieces of mycelium were inoculated and incubated for 13 days at 23 °C in the dark without agitation. Reagents and solvents: 4-Hydroxybutylamine, dichloromethane, triethylamine, benzenesulfonyl chloride, formic acid, n-hexane, acetonitrile, and methanol were purchased from conventional laboratory suppliers. HPLC: Analytical HPLC separation was performed on an HPLC system (Shimadzu Prominenz system, consisting of a CBM 20A communication bus module, an SPD M20A diode array detector, a DGU 20A5R degassing unit, an LC 20AT liquid chromatograph, and a SIL 20A HT auto sampler) using an analytical HPLC column (YMC ODS-A HPLC column, length: 150 mm, diameter: 4.6 mm, pore size: 120 Å, particle size: 5 µM). A solvent system consisting of mobile phase A: water and B: methanol was used as the gradient system; flow rate: 0.8 ml / min; gradient: (A : B): 95 : 5 (2 min) in 20 min to 0 : 100 (5 min). Assay (Leaf-Spot Bioassay) The herbicidal activity of individual substances was tested using a modified leaf-spot assay (Evidente 1995) on Arabidopsis thaliana Col-0. Aliquots of the test substances were dissolved in methanol / water 2:3 (v / v). The substances were tested at concentrations ranging from 5 mmol / L to 25 mmol / L. Several spots of 5 µL each were applied to each leaf (depending on leaf size). The plants were incubated for 72 h in a greenhouse (19°C, day / night cycle). Paraquat (100 µmol / L, solvent methanol:water, 1:1, v / v) served as the positive control, and the solvent methanol:water (1:1 or 2:3, v / v) served as the negative control. After 72 h, the degree of necrosis was determined. The evaluation was carried out photographically according to phenotype (Fig.1). Destructive Leaf Disc The leaf disc assay (non-destructive leaf disc bioassay) with delayed fluorescence measurement was performed as known in the art. The substances were tested in four biological replicates. Arabidopsis thaliana Col-0 and Secale cereale were used as test plants. Testing was carried out in a 96-well plate with a volume of 200 µL per well. Methanol stock solutions (100 and 200 mmol / L) of the substances (compounds (2) and (10)) were prepared. These stock solutions were diluted in leaf disc assay buffer to the desired doses (0.1–5 mmol / L). The tested concentration is indicated for each compound (Fig. 2). The final methanol concentration in 200 µL of test mixture per well was a maximum of 2.5%. The leaf disc assay buffer (pH 6.5) consisted of 19.52 mg (1.0 mmol / L) 2-morpholinoethanesulfonic acid and 1 g (2.9 mmol / L) sucrose in 100 ml distilled water.Leaf discs were cut from unfolded green leaves (punch with pestle, 5 mm diameter) and used for the leaf disc assay. Using a pestle, the individual leaf discs were carefully placed on the surface of the buffer or test solution (with the adaxial surface facing up). The 96-well plate was then incubated in the greenhouse for 72 h (19°C, day / night cycle). Before data acquisition, the plates were wrapped in aluminum foil and acclimated to darkness for 20 min. The Nightshade LB 985 fluorescence imaging device from Berthold Technologies (software: IndiGo, version 2.0.1.00) was used to measure delayed fluorescence after 0 h, 24 h, and 48 h. Figure 2A shows the result for Arabidopsis thaliana Col-0, and Figure 2B the result for Secale cereale. In addition, the appearance of the leaf discs was recorded in daylight after 0 h, 24 h, and 48 h. The samples were irradiated with halogen lamps for 10 minutes.After ten minutes, the light was turned off for 3 s before the delayed fluorescence measurement began. The camera (Peltier / air-cooled slow-scan CCD camera, resolution: 1024 x 1024 pixels) was set to high-scan mode with low gain and a binning of 2x2 (x-binning: 2, y-binning: 2). Background correction and cosmic suppression were activated. Delayed fluorescence was measured for 60 s. The photo was taken with an illumination intensity of 10%. The sample was exposed for 0.1 s for the photo. The sample size corresponded to the dimensions of the 96-well plate (w = 130 mm, h = 15 mm). Delayed fluorescence is described in the state of the art as an indicator of plant stress induced by various environmental influences, including herbicides. In the leaf disc assay, the coloration of the leaf discs correlates with the intensity of the measured delayed fluorescence.High intensity is indicated by a red to yellow-green coloration, while weak intensity is indicated by a blue coloration. If no delayed fluorescence is measurable, only a gray-black leaf disc is visible. This means that the plant no longer has any photosynthetic activity and is therefore dead. In the daylight image, the effect is recognizable by a color change of the leaf disc from green to creamy white. Example 3: Whole Plant Test The active substances were tested on the whole plant using a spray test on Nicotiana benthamiana. For this purpose, 30 ml of an aqueous solution with pH = 8.5 (NaOH) of the active substance (compound (2), 1.9 mmol) was prepared with the addition of 1-propanol (20 ml) and the additives Silwet Gold (38 µl) and Hasten (125 µl). 0.5 ml of the active solution was applied to the test plant in short sprays. Figure 3 shows the result after 6 and 8 days.The solvent without compound (2) served as a negative control. Example 4: Isolation of Natural Product 1 The isolation of natural product (1) is carried out activity-guided using the leaf drop assay. The culture filtrate from 100 flasks is separated from the mycelium-covered cotton balls and successively shaken against ethyl acetate. The mycelium is extracted with ethyl acetate (6 x 3 L) in an ultrasonic bath for 15 minutes. The two organic phases from the filtrate and mycelium extraction are combined, dried with anhydrous sodium sulfate, and concentrated to dryness under reduced pressure in a rotary evaporator (23 g). The resulting extract is dissolved in acetonitrile and partitioned against n-hexane. The acetonitrile phase is separated and concentrated to dryness under reduced pressure (2.56 g). The acetonitrile extract is separated on polyamide SC-6-Ac using a step gradient (n-hexane, ethyl acetate, acetone, methanol).The ethyl acetate fraction containing 1 is collected, the solvent is removed under reduced pressure, and then further purified on silanized silica using a chloroform:methanol gradient (100:1 to chloroform:methanol 1:1, v / v). The final isolation of 1 is achieved by analytical HPLC (tR = 17.3 min; 0.5 mg). Spectroscopic data (1): Rf = 0.27 (SiO2, n-hexane / ethyl acetate, 1:1). 1 H (400 MHz, methanol-d4) δ 7.84 (m, 2H, H-1 / 5), δ 7.56 (m, 2H, H-2 / 4), δ 7.61 (m, 1H, H-3), δ 2.86 (m, 2H, H-7), δ 1.50 (m, 2H, H-8), δ 1.50 (m, 2H, H-9), δ 3.49 (m, 2H, H-10); 13 C (100 MHz, methanol-d4) δ 127.7 (C-1 / 5), δ 129.9 (C-2 / 4), δ 133.2 (C-3), δ 141.9 (C-6), δ 43.6 (C-7), δ 26.9 (C-8), δ 30.3 (C-9), δ 62.1 (C-10). HRESIMS m / z 228.0695 [MH]-, calculated for C10H14NO3S- m / z 228.0700). -benzenesulfonamide (1a, Scheme 1) Scheme 1: Synthesis of 1a. The synthesis of 1a was carried out as known in the art (Scheme 1). 0.184 ml (2 mmol) of 4-amino-1-butanol was dissolved in 10 ml of dry dichloromethane. The solution was then cooled to 0 °C, and 0.28 ml (2 mmol) of dry triethylamine, followed by 0.256 ml of benzenesulfonyl chloride (2 mmol) were added with stirring. The reaction mixture was allowed to warm to room temperature and stirred until the reactants were consumed. The reaction was monitored by thin-layer chromatography on silica gel (mobile phase: n-hexane / ethyl acetate 1:1, v / v).After the reaction, the mixture is evaporated to dryness on a rotary evaporator. The resulting residue is dissolved in n-hexane / ethyl acetate (1:1, v / v) with the addition of a few drops of methanol. The product is purified by column chromatography on silica gel using a step gradient [n-hexane / ethyl acetate (1:1, v / v) → ethyl acetate → ethyl acetate / methanol (7:3, v / v)] to obtain the product as a colorless oil (394 mg, 1.72 mmol, 86%). The synthetic product 1a is identical to natural product 1 in all spectroscopic data. Analytical data (1a): Rf = 0.27 (SiO2, n-hexane / ethyl acetate, 1:1). 1 H (400 MHz, methanol-d4) δ 7.84 (m, 2H, H-1 / 5), δ 7.58 (m, 2H, H-2 / 4), δ 7.58 (m, 1H, H-3), δ 2.86 (m, 2H, H-7), δ 1.50 (m, 2H, H-8), δ 1.50 (m, 2H, H-9), δ 3.49 (m, 2H, H-10) ); 13C (100 MHz, methanol-d4) δ 127.9 (C-1 / 5), δ 130.2 (C-2 / 4), δ 133.5 (C-3), δ 141.9 (C-6), δ 43.9 (C-7), δ 27.1 (C-8), δ 30.6 (C-9), δ 62.3 (C-10); HRESIMS m / z 228.0695 [MH]-, calculated for C10H14NO3S- m / z 228.0700). General synthesis procedure The corresponding sulfonyl chloride was slowly added dropwise to a solution of the respective amino alcohol (1.5 equivalents) and dry triethylamine (NEt3, 2 equivalents) in dry dichloromethane (DCM, 12 ml) at 22 °C. Stirring was continued at 22 °C for 3 hours, the volatiles were removed at 30 °C under reduced pressure on a rotary evaporator, and the residue was purified by column chromatography (silica gel, n-hexane / ethyl acetate mixtures). 4-(tert-butyl)-N-(5-hydroxypentyl)benzenesulfonamide (Compound (2)) According to the general synthesis procedure, 2 (603 mg, 2.01 mmol, 93%) was obtained as a colorless waxy solid from 4-(tert-butyl)benzenesulfonyl chloride (500 mg, 2.15 mmol) and 5-aminopentanol (332 mg, 3.22 mmol). Rf = 0.20 (SiO2, n-hexane / ethyl acetate, 6:4); mp= 53 - 54°C; UV-Vis (MeOH): λmax (log ε) = 228 nm (4,02); IR (ATR): ν = 3286m, 2933m, 2863w, 1597w, 1473w, 1462w, 1424m, 1399w, 1362w, 1331m, 1318s, 1292m, 1268w, 1199w, 1158s, 1112m, 1088m, 1048s, 1016w, 887m, 843m, 826m, 755m, 735w, 689m, 638m, 630s, 573vs, 552s, 525m, 502w cm. −1 ; 1 H-NMR (500 MHz, DMSO-d6): δ = 7,72 – 7,68 (m, 2H, 2-H, 2'-H), 7,62 – 7,58 (m, 2H, 3-H, 3'-H), 7,46 (t, J = 5,7 Hz, 1H, NH), 4,30 (t, J = 5,1 Hz, 1H, OH), 3,34 – 3,29 (m, 2H, 11-H), 2,73 – 2,68 (m, 2H, 7-H), 1,39 – 1,31 (m, 4H, 8-H, 10-H), 1,30 (s, 9H, 6-H, 6'-H, 6''-H), 1,26 – 1,15 (m, 2H, 9-H) ppm; 13 C-NMR (101 MHz, DMSO-d6): δ = 155,2 (C-4), 137,8 (C-1), 126,3 (C-2), 125,9 (C-3), 60,5 (C-11), 42,6 (C-7), 34,8 (C-5), 32,0 (C-10), 30,8 (C-6), 28,9 (C-8), 22,6 (C-9) ppm; MS (ESI, MeOH): m / z 322,4 (100 %, [M+Na] +); HRESIMS: m / z 322.14460; Analysis calculated: C, 60.17; H, 8.42; N, 4.68; Found: C, 59.84; H, 8.67; N, 4.50. 4-(tert-butyl)-N-(2-hydroxyethyl)benzenesulfonamide (compound (3)) According to the general synthesis procedure, 3 (435 mg, 1.69 mmol, 79%) was obtained as a colorless waxy solid from 4-(tert-butyl)benzenesulfonyl chloride (500 mg, 2.15 mmol) and 2-aminoethanol (197 mg, 3.22 mmol). Rf = 0.20 (SiO2, n-hexane / ethyl acetate, 6:4); mp = 75-77°C; UV-Vis (MeOH): λmax (log ε) = 228 nm (4.10); IR (ATR): ν = 3522w, 3162w, 3072vw, 2952w, 2903w, 2891w, 2868w, 1596w, 1463w, 1450w, 1432w, 1400w, 1364w, 1354vw, 1325s, 1308m, 1291w, 1261w, 1207vw, 1198w, 1161vs, 1115m, 1087m, 1071m, 1057s, 1016w, 955m, 905w, 844w, 831vw, 823m, 763s, 726m, 624s, 580vs, 550s, 515vw, 498vw, 473w, 457w, 421w, 411w cm −1 ; 1H-NMR (400 MHz, DMSO-d6): δ = 7,75 – 7,70 (m, 2H, 2-H, 2'-H), 7,63 – 7,58 (m, 2H, 3-H, 3'-H), 7,50 (s, 1H, NH), 4,66 (t, J = 5,5 Hz, 1H, OH), 3,37 (q, J = 6,0 Hz, 2H, 8-H), 2,77 (t, J = 6,4 Hz, 2H, 7-H), 1,30 (s, 9H, 6-H, 6'-H, 6''-H) ppm; 13 C-NMR (101 MHz, DMSO-d6): δ = 155,2 (C-4), 137,7 (C-1), 126,4 (C-2), 125,9 (C-3), 59,9 (C-8), 45,1 (C-7), 34,8 (C-5), 30,8 (C-6) ppm; MS (ESI, MeOH): m / z 280,4 (100 %, [M+Na] + );HRESIMS: m / z 280,09753; Analyse berechnet: C, 56,01; H, 7,44; N, 5,44; gefunden: C, 55,83; H, 7,69; N, 5,25. (Compound (4)) Following the general synthesis procedure, 4 (530 mg, 1.95 mmol, 91%) was obtained from 4-(tert-butyl)benzenesulfonic acid chloride (500 mg, 2.15 mmol) and 3-aminopropanol (242 mg, 3.22 mmol) as a colorless waxy solid. Rf = 0.20 (SiO2, n-hexane / ethyl acetate, 6:4); mp = 63-65°C; UV-Vis (MeOH): λmax (log ε) = 228 nm (4.15); IR (ATR): ν = 3311m, 3241m, 2963m, 2870w, 1597w, 1472w, 1426m, 1402m, 1363w, 1334m, 1313s, 1292m, 1270w, 1203w, 1160vs, 1112m, 1088m, 1069m, 1027m, 1008m, 960m, 908w, 847w, 834m, 826m, 756s, 704m, 625s, 578vs, 550s, 512m, 487m, 475w, 461w cm −1 ; 1 H NMR (400 MHz, DMSO-d6): δ = 7.73 – 7.68 (m, 2H, 2-H, 2'-H), 7.63 – 7.58 (m, 2H, 3-H, 3'-H), 7.43 (s, 1H, NH), 4.40 (s, 1H, OH), 3.37 (td, J = 6.2, 2.8 Hz, 2H, 9-H), 2.77 (t, J = 7.3 Hz, 2H, 7-H), 1.58 - 1.49 (m, 2H, 8-H), 1.30 (s, 9H, 6-H, 6'-H, 6''-H) ppm; 13C-NMR (101 MHz, DMSO-d6): δ = 155.2 (C-4), 137.6 (C-1), 126.4 (C-2), 126.0 (C-3), 58.1 (C-9), 40.0 (C-7), 34.8 (C-5), 32.4 (C-8), 30.8 (C-6) ppm; MS (ESI, MeOH): m / z 294.1 (100%, [M+Na] + ); HRESIMS: m / z 294.11316; Analysis calculated: C, 57.54; H, 7.80; N, 5.16; Found: C, 57.21; H, 8.03; N, 5.96. (Compound (5)) According to the general synthesis procedure, 5 (518 mg, 1.81 mmol, 84%) was obtained as a colorless waxy solid from 4-(tert-butyl)benzenesulfonic acid chloride (500 mg, 2.15 mmol) and 4-aminobutanol (287 mg, 3.22 mmol). Rf = 0.20 (SiO2, n-hexane / ethyl acetate, 6:4); mp = 58-60°C; UV-Vis (MeOH): λmax (log ε) = 228 nm (4.15); IR (ATR): ν = 3452w, 3248w, 3115w, 2962w, 2944m, 2867w, 1594w, 1471w, 1463w, 1435w, 1400w, 1364w, 1316s, 1291m, 1267w, 1197w, 1154s, 1111m, 1084m, 1065m, 1038m, 1018w, 988w, 909w, 839m, 753m, 735w, 685w, 627s, 581vs, 549s, 514w, 489w, 472w, 464w cm −1 ; 1H-NMR (400 MHz, DMSO-d6): δ = 7,73 – 7,68 (m, 2H, 2-H, 2'-H), 7,62 – 7,58 (m, 2H, 3-H, 3'-H), 7,47 (s, 1H, NH), 4,35 (s, 1H, OH), 3,35 – 3,29 (m, 2H, 10-H), 2,75 – 2,69 (m, 2H, 7-H), 1,44 – 1,33 (m, 4H, 8-H, 9-H), 1,30 (s, 9H, 6-H, 6'-H, 6''-H) ppm; 13 C-NMR (101 MHz, DMSO-d6): δ = 155,1 (C-4), 137,8 (C-1), 126,3 (C-2), 125,9 (C-3), 60,2 (C-10), 42,5 (C-7), 34,8 (C-5), 30,8 (C-6), 29,5 (C-9), 25,8 (C-8) ppm; MS (ESI, MeOH): m / z 308,3 (100 %, [M+Na] +); HRESIMS: m / z 308.12892; Analysis calculated: C, 58.92; H, 8.12; N, 4.91; Found: C, 58.77; H, 8.41; N, 4.67. N-(6-hydroxyhexyl)-4-methylbenzenesulfonamide (Compound (6)) According to the general synthesis procedure, 6 (551 mg, 2.03 mmol, 77%) was obtained as a colorless waxy solid from 4-methylbenzenesulfonyl chloride (500 mg, 2.62 mmol) and 6-aminohexanol (461 mg, 3.93 mmol). Rf = 0.15 (SiO2, n-hexane / ethyl acetate, 6:4); mp = 49-50°C; UV-Vis (MeOH): λmax (log ε) = 227 nm (4.10); IR (ATR): ν = 3423w, 3364w, 3290m, 2936m, 2891w, 2860w, 1589w, 1495w, 1476w, 1422m, 1385w, 1319m, 1303w, 1290w, 1154vs, 1091m, 1067m, 1036m, 983w, 905m, 817s, 734w, 707w, 666s, 573s, 549s, 523m, 484w, 430w cm −1 ; 1H-NMR (400 MHz, DMSO-d6): δ = 7,70 – 7,63 (m, 2H, 2- H, 2'-H), 7,47 – 7,41 (m, 1H, NH), 7,41 – 7,35 (m, 2H, 3-H, 3'-H), 4,30 (t, J = 5,1 Hz, 1H, OH), 3,38 – 3,30 (m, 2H, 11-H), 2,73 – 2,65 (m, 2H, 6-H), 2,37 (s, 3H, 5-H), 1,41 – 1,27 (m, 4H, 7-H, 10-H), 1,22 – 1,14 (m, 4H, 8-H, 9-H) ppm; 13 C-NMR (101 MHz, DMSO-d6): δ = 142,4 (C-4), 137,8 (C-1), 129,6 (C-3, C-3'), 126,5 (C-2, C-2'), 60,6 (C-11), 42,5 (C-6), 32,4 (C-10), 29,0 (C-7), 25,9 (C-9), 25,0 (C-8), 20,9 (C-5) ppm; MS (ESI, MeOH): m / z 294 (100 %, [M+Na] +); HRESIMS: m / z 294.11332; Analysis calculated: C, 57.54; H, 7.80; N, 5.16; Found: C, 57.36; H, 8.01; N, 5.03. 3-(tert-butyl)-N-(2-hydroxyethyl)benzenesulfonamide (Compound (7)) According to the general synthesis procedure, 7 (522 mg, 2.03 mmol, 94%) was obtained as a colorless oil from 3-(tert-butyl)benzenesulfonic acid chloride (500 mg, 2.15 mmol) and 2-aminoethanol (197 mg, 3.22 mg). Rf = 0.20 (SiO2, n-hexane / ethyl acetate, 6:4); UV-Vis (MeOH): λmax (log ε) = 224 nm (4.04); IR (ATR): ν = 3500w, 3276w, 2962w, 2872w, 1481m, 1460w, 1416m, 1398w, 1366w, 1325m, 1307s, 1267w, 1205vw, 1156vs, 1125m, 1096m, 1057m, 998vw, 949m, 896w, 865w, 796m, 775w, 696s, 678m, 625m, 586vs, 545m, 534m, 524m, 481w, 456w cm −1 ; 1H-NMR (400 MHz, DMSO-d6): δ = 7.82 – 7.80 (m, 1H, 2-H), 7.67 (ddd, J = 7.8, 2.0, 1.1 Hz, 1H, 6-H), 7.62 (ddd, J = 7.8, 1.8, 1.1 Hz, 1H, 4- H), 7.58 (s, 1, NH), 7.51 (td, J = 7.8, 0.5 Hz, 1H, 5-H), 4.67 (t, J = 5.5 Hz, 1H, OH), 3.37 (q, J = 6.1 Hz, 2H, 10-H), 2.79 (t, J = 6.4 Hz, 2H, 9-H), 1.31 (s, 9H, 8-H, 8'-H, 8''-H) ppm; 13 C-NMR (101 MHz, DMSO-d6): δ = 151.9 (C-3), 140.4 (C-1), 129.3 (C-4), 128.9 (C-5), 123.7 (C-2), 122.9 (C-6), 59.9 (C-10), 45.1 (C-9), 34.7 (C-7), 30.9 (C-8) ppm; MS (ESI, MeOH): m / z 280.3 (100%, [M+Na] + ); HRESIMS: m / z 280.11005; Analysis calculated: C, 56.01; H, 7.44; N, 5.44; Found: C, 55.86; H, 7.70; N, 5.24. 3-(tert-butyl)-N-(3-hydroxypropyl)benzenesulfonamide (Compound (8)) According to the general synthesis procedure, 8 (572 mg, 2.11 mmol, 98%) was obtained as a colorless oil from 3-(tert-butyl)benzenesulfonic acid chloride (500 mg, 2.15 mmol) and 3-aminopropanol (242 mg, 3.22 mg). R f = 0.23 (SiO 2, n-Hexan / Essigsäureethylester, 6:4); UV-Vis (MeOH): λ max (log ε) = 224 nm (4,15); IR (ATR): ν = 3501w, 3276w, 2961m, 2873w, 1481m, 1460w, 1416w, 1398w, 1366w, 1324m, 1307s, 1267w, 1178w, 1155vs, 1125m, 1084m, 1069m, 1008w, 998w, 960w, 876w, 798m, 774m, 696s, 678m, 625m, 586vs, 534m, 491m, 460w cm −1 ; 1 H-NMR (400 MHz, DMSO-d6): δ = 7,79 (td, J = 1,9, 0,5 Hz, 1H, 2-H), 7,67 (ddd, J = 7,8, 2,0, 1,1 Hz, 1H, 6-H), 7,61 (ddd, J = 7,7, 1,8, 1,2 Hz, 1H, 4-H), 7,52 (td, J = 7,5, 1,8 Hz, 2H, 5-H, NH), 4,39 (t, J = 5,1 Hz, 1H, OH), 3,36 (td, J = 6,2, 4,5 Hz, 2H, 11-H), 2,79 (td, J = 7,5, 3,6 Hz, 2H, 9-H), 1,55 – 1,46 (m, 2H, 10-H), 1,31 (s, 9H, 8-H, 8'-H, 8''-H) ppm; 13 C-NMR (101 MHz, DMSO-d6): δ = 151,9 (C-3), 140,3 (C-1), 129,3 (C-4), 128,9 (C-5), 123,7 (C-2), 122,9 (C-6), 58,0 (C-11), 40,0 (C-9), 34,7 (C-7), 32,3 (C-10), 30,9 (C-8) ppm; MS (ESI, MeOH): m / z 294,1 (100 %, [M+Na] +); HRESIMS: m / z 294.11321; Analysis calculated: C, 57.54; H, 7.80; N, 5.16; Found: C, 57.25; H, 8.03; N, 4.99. (Compound (9)) Following the general synthesis procedure, 9 (589 mg, 2.06 mmol, 96%) was obtained as a colorless oil from 3-(tert-butyl)benzenesulfonic acid chloride (500 mg, 2.15 mmol) and 4-aminobutanol (287 mg, 3.22 mmol). Rf = 0.20 (SiO2, n-hexane / ethyl acetate, 6:4); UV-Vis (MeOH): λmax (log ε) = 224 nm (3.90); IR (ATR): ν = 3499w, 3280w, 2959m, 2870w, 1481m, 1460w, 1416w, 1398w, 1366w, 1324m, 1307m, 1267w, 1156vs, 1125m, 1088m, 1056m, 1034w, 998w, 872w, 797m, 773w, 696s, 678m, 626m, 586vs, 535m, 520m, 496w, 464w cm −1 ; 1 H-NMR (400 MHz, DMSO-d6): δ = 7.81 – 7.78 (m, 1H, 2-H), 7.66 (ddd, J = 7.8, 2.0, 1.1 Hz, 1H, 6-H), 7.61 (ddd, J = 7.8, 1.8, 1.1 Hz, 1H, 4-H), 7.56 - 7.48 (m, 2H, 5-H, NH), 4.35 (s, 1H, OH), 3.37 - 3.27 (m, 2H, 12-H), 2.77 - 2.70 (m, 2H, 9-H), 1.43 - 1.32 (m, 4H, 10-H, 11-H), 1.31 (s, 9H, 8-H, 8'-H, 8''-H) ppm;13 C-NMR (101 MHz, DMSO-d6): δ = 151.9 (C-3), 140.5 (C-1), 129.2 (C-4), 128.9 (C-5), 123.7 (C-2), 122.9 (C-6), 60.2 (C-12), 42.5 (C-9), 34.7 (C-7), 30.9 (C-8), 29.5 (C-11), 25.7 (C-10) ppm; MS (ESI, MeOH): m / z 308.4 (100%, [M+Na] + ); HRESIMS: m / z 308.12899; Analysis calculated: C, 58.92; H, 8.12; N, 4.91; found: C, 58.73; H, 8.33; N, 4.77. 3-(tert-butyl)-N-(5- (Compound (10)) Following the general synthesis procedure, 10 (610 mg, 2.04 mmol, 95%) was obtained as a colorless oil from 3-(tert-butyl)benzenesulfonic acid chloride (500 mg, 2.15 mmol) and 5-aminopentanol (332 mg, 3.22 mmol). Rf = 0.23 (SiO2, n-hexane / ethyl acetate, 6:4); UV-Vis (MeOH): λmax (log ε) = 224 nm (3.90); IR (ATR): ν = 3503w, 3278w, 2939m, 2868w, 1481m, 1459w, 1416w, 1398w, 1366w, 1325m, 1307m, 1267w, 1156vs, 1125m, 1087m, 1040m, 998w, 898w, 797w, 774w, 697s, 678m, 626m, 586vs, 534m, 501w, 478w, 461w cm −1 ; 1H- NMR (400 MHz, DMSO-d6): δ = 7,79 (td, J = 1,9, 0,5 Hz, 1H, 2-H), 7,66 (ddd, J = 7,8, 2,0, 1,1 Hz, 1H, 6-H), 7,61 (ddd, J = 7,7, 1,8, 1,2 Hz, 1H, 4-H), 7,55 – 7,48 (m, 2H, 5-H, NH), 4,30 (t, J = 5,1 Hz, 1H, OH), 3,35 – 3,27 (m, 2H, 13-H), 2,72 (q, J = 6,2 Hz, 2H, 9-H), 1,38 – 1,31 (m, 4H, 10-H, 12-H), 1,31 (s, 9H, 8-H, 8'-H, 8''-H), 1,26 – 1,17 (m, 2H, 11-H) ppm; 13 C-NMR (126 MHz, DMSO-d6): δ = 151,9 (C-3), 140,5 (C-1), 129,2 (C-4), 128,9 (C-5), 123,7 (C-2), 122,8 (C-6), 60,5 (C-13), 42,6 (C-9), 34,7 (C-7), 32,0 (C-12), 30,9 (C-8), 28,8 (C-10), 22,6 (C-11) ppm; MS (ESI, MeOH): m / z 322,3 (100 %, [M+Na] +); HRESIMS: m / z 322.14472; Analysis calculated: C, 60.17; H, 8.42; N, 4.68; Found: C, 59.76; H, 8.69; N, 15.81. 4-Cyclohexyl-N-(2-hydroxyethyl)benzenesulfonamide (Compound (11)) According to the general synthesis procedure, 11 (453 mg, 83%) was obtained as a colorless, highly viscous liquid from 4-cyclohexylbenzene-1-sulfonic acid chloride (500 mg, 1.93 mmol) and 2-aminoethanol (177 mg, 2.90 mmol). Rf = 0.56 (SiO2, chloroform / ethyl acetate, 4:6); UV-Vis (MeOH): λmax (log ε) = 229 nm (4.19); IR (ATR): ν = 3514vw, 3264w, 3146w, 2920m, 2848m, 1597w, 1496vw, 1483vw, 1461w, 1451m, 1427w, 1409w, 1348w, 1319s, 1278w, 1260w, 1216vw, 1188w, 1156s, 1134w, 1093s, 1059m, 1036m, 1018w, 996w, 953m, 890w, 864vw, 842w, 826s, 802w, 782vw, 731w, 701s, 631w, 597s, 574vs, 527m, 504w, 491w, 479w, 458m cm −1 ; 1 H-NMR (400 MHz, DMSO-d 6): δ = 7.72 – 7.68 (m, 2H, 2- H, 2'-H), 7.51 – 7.46 (m, 1H, NH), 7.45 – 7.40 (m, 2H, 3-H, 3'-H), 4.66 (t, J = 5.6 Hz, 1H, OH), 3.37 (td, J = 6.3, 5.5 Hz, 2H, 10-H), 2.81 – 2.74 (m, 2H, 9-H), 2.64 – 2.55 (m, 1H, 5-H), 1.84 – 1.74 (m, 4H, 6-Ha, 6'-Ha, 7-Ha, 7'-Ha), 1.74 – 1.66 (m, 1H, 8-Ha), 1.50 – 1.30 (m, 4H, 6-Hb, 6'-Hb, 7-Hb, 7'-Hb), 1.30 – 1.17 (m, 1H, 8-Hb) ppm; 13 C-NMR (101 MHz, DMSO-d6): δ = 152.1 (C-4), 138.0 (C-1), 127.4 (C-2), 126.6 (C- 3), 59.9 (C-10), 45.1 (C-9), 43.6 (C-5), 33.5 (C-6), 26.2 (C-7), 25.4 (C-8) ppm; MS (ESI, MeOH): m / z 305.9 (90 %, [M+Na] + ); HRESIMS: m / z 306.11403; Analyse berechnet: C, 59.34; H, 7.47; N, 4.94; gefunden: C, 59.07; H, 7.73; N 4.69.

Claims

Claims 1. Use of a compound of formula (I) or a salt thereof as a herbicide: where R 1 is selected from the group consisting of (i) an unsubstituted (C2-C12) alkyl alcohol, (ii) an unsubstituted (C2-C12) alkenyl alcohol, and (iii) an unsubstituted (C2-C12) alkynyl alcohol; R 2 , R 3 , R 4 , R 5 and R 6 are each independently selected from the group consisting of hydrogen (H), halogen (F, Cl, Br, I), hydroxyl (OH), a linear or branched (C1-C6)-alkyl, a linear or branched O-(C1-C6)-alkyl, a (C3-C6)-cycloalkyl, and a (C3-C6)-cycloalkoxy; and m is 0, 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10.

2. Use according to claim 1, wherein R 1 is selected from the group consisting of (i) an unsubstituted (C2-C8) alkyl alcohol, (ii) an unsubstituted (C2-C8) alkenyl alcohol, and (iii) an unsubstituted (C2-C8)-alkynyl alcohol.

3. Use according to claim 1 or claim 2, wherein R 1 is an unsubstituted (C2-C8) alkyl alcohol.

4. Use according to any one of claims 1 to 3, wherein R 2 , R 3 , R 4 , R 5 and R 6 are each independently selected from the group consisting of hydrogen (H), halogen (F, Cl, Br, I), a linear or branched (C1-C4)-alkyl, hydroxyl (OH), a linear or branched O-(C1-C4)-alkyl.

5. Use according to any one of claims 1 to 4, wherein one of the groups R 2 , R 3 , R 4 , R 5 and R 6 tert-butyl, the remaining groups R 2 , R 3 , R 4 , R 5 and R 6 are each H, m is 0, and R 1 is an unsubstituted (C5-C7) alkyl alcohol.

6. Use according to any one of claims 1 to 4, wherein one of the groups R 2 , R 3 , R4 , R 5 and R 6 Cyclohexyl, the remaining R 2 , R 3 , R 4 , R 5 and R 6 are each H, m is 0, and R 1 is an unsubstituted (C2-C4)-alkyl alcohol.

7. Use according to any one of claims 1 to 4, wherein m is 0.

8. Use according to claim 1, wherein the compound of formula (I) is selected from the group consisting of compounds (2), (10) and 9. Use according to claim 1, wherein the compound of formula (I) is selected from the group consisting of 4-(tert-butyl)-N-(2-hydroxyethyl)benzenesulfonamide (compound (3)), 4-(tert-butyl)-N-(3-hydroxypropyl)benzenesulfonamide (compound (4)), 4-(tert-butyl)-N-(4-hydroxybutyl)benzenesulfonamide (compound (5)), N-(6-hydroxyhexyl)-4-methylbenzenesulfonamide (compound (6)), 3-(tert-butyl)-N-(2-hydroxyethyl)benzenesulfonamide (compound (7)), 3-(tert-butyl)-N-(3-hydroxypropyl)benzenesulfonamide (compound (8)), 3-(tert-butyl)-N-(4-hydroxybutyl)benzenesulfonamide (compound (9)), and 4-Cyclohexyl-N-(2-hydroxyethyl)benzenesulfonamide (Compound (11)).

10. A method for controlling one or more weeds, comprising applying to a plant or parts of a plant an effective amount of a compound of formula (I) or a salt thereof, as defined in any one of claims 1 to 9.Method according to claim 10, wherein the method is applied preventively or curatively.

12. The method according to claim 10 or claim 11, wherein the compound of formula (I) or the salt thereof is present in an aqueous solution, the concentration of the compound of formula (I) or the salt thereof in the aqueous solution being in the range of 1 µM to 10 mM.

13. The method according to any one of claims 10 to 12, wherein the compound of formula (I) or the salt thereof is in the form of a carrier composition mixture, the compound of formula (I) or the salt thereof being present in an amount of 0.001 to 99 wt.%, based on the carrier composition mixture.

14. The method according to claim 13, wherein the carrier composition mixture comprises one or more dispersible, inert carriers. 15.A process according to any one of claims 10 to 14, wherein the compound of formula (I) or the salt thereof is applied as a high volume hydraulic spray, a low volume hydraulic spray, an ultra-low volume spray, by high pressure liquid injection, by gap injection, as a forced air spray, as an air spray, or as a dust.

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