HIGHLY EFFECTIVE FORMULATIONS BASED ON 2-[(2,4-DICHLORPHENYL)-METHYL]-4,4'-DIMETHYL-3-ISOXAZOLIDINONE AND / OR FLUFENACET
Patent Information
- Authority / Receiving Office
- DE · DE
- Patent Type
- Patents
- Current Assignee / Owner
- BAYER AG
- Filing Date
- 2020-09-09
- Publication Date
- 2026-06-11
AI Technical Summary
Existing agrochemical formulations for pre-emergence herbicides like DCPMI and flufenacet suffer from inconsistent efficacy under varying moisture conditions, often requiring high application rates and lacking effectiveness under dry conditions, with limited adjuvants improving soil uptake and selectivity towards different cultures.
Formulations containing DCPMI and/or flufenacet with dispersants, efficacy enhancers such as organically modified (poly)-glycosides, and optional safeners, thickeners, and water, optimized to enhance herbicide uptake by seeds and germinating plants, maintaining high efficacy under both moist and dry conditions.
The formulations provide significantly improved weed and grass control with consistent efficacy across moisture conditions, maintaining selectivity towards different cultures.
Description
[0001] The present invention relates to formulations based on 2-[(2,4-Dichlorophenyl)-methyl]-4,4'-dimethyl-3-isoxazolidinone and / or flufenacet, their preparation and mixtures and their use as an agrochemical formulation with improved biological activity and increased weed and grass control.
[0002] The active ingredient 2-[(2,4-Dichlorophenyl)-methyl]-4,4'-dimethyl-3-isoxazolidinone (CAS number 81777-95-9 or IUPAC 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, hereinafter abbreviated as DCPMI), as well as, for example, flufenacet, a pre-emergence herbicide, and 4'-fluoro-N-isopropyl-2-(5-trifluoromethyl-1,3,4-thiadiazol-2-yloxy)acetanilide, hereinafter abbreviated as FFA, are herbicidal active ingredients. These two active ingredients are typically used in aqueous formulations such as capsule suspensions and suspension concentrates. The formulations are usually applied pre-emergence, with pre-emergence referring here to the emergence of weeds and grasses. In this process, the active ingredients do not work via leaf absorption, but are distributed on the soil and subsequently absorbed via the root, the seed and / or the emerging plant (hypocotyl).
[0003] DCPMI is used in herbicidal compositions and mixtures or as a selective grass herbicide, as described, for example, in WO2015 / 127259 A1 or WO2012 / 148689 A. Capsule suspensions (CS) and suspension concentrates (SC) of DCPMI are known from WO2019 / 076744, WO2018 / 024839 and WO2019 / 211263 as well as WO2015 / 127259.
[0004] Typically, active ingredient formulations for foliar applications are optimized by the addition of penetration enhancers, such as oils or ethoxylated alcohols, so that the active ingredient quickly penetrates the plant through the leaf.
[0005] In contrast, only a few adjuvants are known for soil application that improve uptake into seeds, germinating plants, or roots. Furthermore, the mechanism of action of these adjuvants is not only unknown in most cases, but their effectiveness is also highly dependent on the active ingredient. Therefore, there are very few known adjuvants that influence soil uptake. Formulations containing so-called humectants, as described in WO2014 / 159948, are known. Phenoxypolyalkylenoxy sulfates or phosphates, as described in WO2018 / 141594, are also known.
[0006] Jiří et al., Plant, Soil and Environment 2017, 63, 409-415, describes an experimental study aimed at comparing the efficacy, selectivity against sunflowers, and dissipation of three pre-emergence herbicides. Fluorochloridone, linuron, and oxyfluorfen were applied individually, and each herbicide was also applied in a tank mix with two different additives (a silicone-based adjuvant and paraffin oil).
[0007] A disadvantage of the known formulations is that their effect on weed control is often insufficient, resulting either in no effect at all, an insufficient effect, or the need for high application rates.
[0008] Capsule suspensions are often used for the application of DCPMI, which are even weaker in their effect than suspension concentrates.
[0009] Furthermore, a disadvantage of existing formulations is that additives often become significantly less effective, or even ineffective, under dry conditions. Since long-term weather forecasting over weeks, or even months in the case of autumn applications, is simply impossible for farmers, there is a need for a reliable formulation that performs consistently well under both damp and wet conditions.
[0010] The object of the invention was therefore to provide optimized formulations that exhibit significantly better efficacy than known formulations under both moist and dry conditions. The optimization of efficacy was to be particularly evident in the pre-emergence stage. The efficacy should not only be improved but also remain consistently high under both moist and dry conditions.
[0011] In addition to increasing effectiveness, it is important to ensure that selectivity towards different cultures is not reduced.
[0012] The problem of the present invention has been solved with the formulations according to the claims.
[0013] Described, but not necessarily in accordance with requirements, are (agrochemical) formulations containing a) DCPMI and / or at least one pre-emergence herbicide, b) at least one dispersant, c) at least one efficacy enhancer selected from the group comprising organically modified (poly)-glycosides and / or furanoses and / or pyranoses, and / or organically modified sorbitans and / or sorbitols, d) optionally at least one of a) different agrochemical active ingredients, e) optionally at least one safener, f) optionally at least one thickener, and g) optionally other additives and excipients, h) water.
[0014] In a preferred embodiment, components d) to g) are necessarily included.
[0015] Suitable pre-emergence herbicides a) may be selected from the group comprising acetochlor, aclonifen, flufenacet, diflufenican, clomazone, pendimethalin, pyroxasulfone, cinmethylin, dimethenamide, and more preferably flufenacet and pyroxasulfone, and particularly preferably flufenacet. Formulations according to the invention contain DCMPI and / or flufenacet.
[0016] The agrochemical active substances d) may be selected from the group of herbicides, insecticides, fungicides and nematicides, preferably d) is another herbicide.
[0017] Also related to the present invention are water-dispersible suspension concentrates (SC), capsule suspension concentrates (CS) and mixtures of SC and CS ((ZC) formulations) obtainable according to the inventive method.
[0018] The SC according to the invention can be produced using methods known in the prior art, e.g., by wet milling the components in bead mills (such as batch or continuous bead mills) or colloid mills (such as dental colloid mills). The CS is produced by interfacial polymerization.
[0019] The proportion of water in the formulations according to the invention can generally be 25 to 98 wt.%, preferably 35 to 85 wt.%, wherein water supplements the proportion of components a) - g) to 100 wt.%.
[0020] The term "wt%" (weight percent) used here and throughout the entire description, unless otherwise defined, refers to the relative weight of the respective component in relation to the total weight of the formulation, where "formulation" here describes the undiluted, not ready-to-use composition.
[0021] The formulation can typically contain residues of organic solvents from the additives of 0 to 5.0 wt.%, more preferably of 0.05 to 4.0 wt.%, and particularly preferably of 0.1 to 2.5 wt.%.
[0022] The proportion of active ingredient a) in the formulations according to the invention is preferably 0.5 to 55.0 wt.%, more preferably 0.5 to 45.0 wt.%, even more preferably 5.0 to 40.0 wt.%, and particularly preferably 10.0 to 40.0 wt.%.
[0023] If further active ingredients d) are included, the total proportion of components a) and d) is preferably 0.5 to 55.0 wt.%, more preferably 0.5 to 45.0 wt.%, even more preferably 5.0 to 40.0 wt.%, and particularly preferably 10.0 to 40.0 wt.%, which means that the proportion of component a) is reduced by component d).
[0024] The proportion of dispersing agent (component b) is preferably 1.0 to 15.0 wt.%, more preferably 2.0 to 10.0 wt.% and most preferably 2.5 to 8.0 wt.%.
[0025] The proportion of efficacy enhancer c) in the formulations according to the invention is 5.0 to 95.0 wt.%, more preferably 10.0 to 90.0 wt.%, and most preferably 20.0 to 80.0 wt.%. According to the invention, the efficacy enhancer is an alkyl polysaccharide.
[0026] The proportion of safeners e) in the formulations according to the invention is preferably from 0 to 20 wt.%, preferably 0 to 15 wt.%, particularly preferably 0 to 10 wt.%.
[0027] In an alternative embodiment which necessarily contains safeners, the proportion of safeners e) in the formulations according to the invention is preferably from 0.01 to 20 wt.%, preferably 0.1 to 15 wt.%, particularly preferably 0.1 to 10 wt.%.
[0028] The proportion of thickeners f) in the formulations according to the invention is preferably from 0 to 2.0 wt.%, preferably 0.01 to 1.00 wt.%, particularly preferably 0.01 to 0.60 wt.%, most preferably 0.04 to 0.50 wt.% and most preferably 0.05 to 0.3 wt.%.
[0029] The proportion of any additional auxiliary and additive materials g) in the dispersions according to the invention is preferably 0 to 20.0 wt.%, preferably 1.0 to 15.0 wt.%, more preferably 3.0 to 10.0 wt.%, and particularly preferably 5.0 to 10.0 wt.%.
[0030] Given the aforementioned proportions of the respective ingredients, it is clear to those skilled in the art that the preferred ranges of the individual ingredients can be freely combined, so these combinations of different preferred ranges of individual ingredients should also be disclosed. However, unless otherwise disclosed, preferred ranges of the same level are particularly preferred, i.e., all preferred or especially preferred ranges, whereby a specific disclosure should not replace these general combinations but rather supplement them. A combination of the most preferred (smallest) preferred ranges is particularly preferred.
[0031] The same applies to other indications of preferred areas at other points in this description.
[0032] In a preferred embodiment, the proportion of the component is a) 0.5 to 55 wt.% b) 1.0 to 15 wt.%, c) 5 to 95 wt.% d) 0% e) 0%, f) 0% to 1.00 wt.%, and g) 0 to 20 wt.%, where water is added to bring the total weight to 100% by weight.
[0033] In a further preferred embodiment, the proportion of the component is a) 0.5 to 45 wt.% b) 1.0 to 15 wt.%, c) 10 to 90 wt.% d) optionally at least one agrochemical active ingredient different from a), e) 0 to 15.0 wt.%, f) 0.01 to 1.00 wt.%, and g) 1 to 15 wt.%, where water is added to bring the total weight to 100% by weight.
[0034] In another preferred embodiment, the proportion of the component is a) 5 to 40 wt.%, b) 2.0 to 10 wt.%, c) 20 to 80 wt.%, d) optionally at least one agrochemical active ingredient different from a), e) 0 to 10.0 wt.%, f) 0.01 to 0.60 wt.%, and g) 3.0 to 10.0 wt.% where water is added to bring the total weight to 100% by weight.
[0035] In another preferred embodiment, the proportion of the component is a) 10 to 40 wt.% b) 2.50 to 8.0 wt.%, c) 20 to 80 wt.% d) at least one agrochemical active ingredient different from a), e) 0 to 10.0 wt.%, f) 0.04 to 0.50 wt.%, and g) 5.0 to 10.0 wt.%, where water is added to bring the total weight to 100% by weight.
[0036] In an alternative embodiment, the proportion of the component is a) 10 to 40 wt.% b) 2.50 to 8.0 wt.%, c) 20 to 80 wt.% d) at least one agrochemical active ingredient different from a), e) 0.1 to 10.0 wt.%, f) 0.04 to 0.50 wt.%, and g) 5.0 to 10.0 wt.%, where water is added to bring the total weight to 100% by weight.
[0037] Dispersants (b) are ionic or non-ionic surfactants. Suitable anionic dispersants (b) such as emulsifiers, surfactants, wetting agents, and dispersants are, for example, alkali, alkaline earth, or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof, such as the salts of alkylsulfonic or alkylphosphoric acids, as well as alkylarylsulfonic or alkylarylphosphoric acids, diphenylsulfonates, alpha-olefin sulfonates, lignosulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates, or sulfosuccinamates. Examples of sulfates include sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters. Examples of phosphates include phosphate esters.Examples of carboxylates include alkyl carboxylates and carboxylated alcohol or alkylphenol ethoxylates. Also suitable are the group of anionic emulsifiers of alkali metal, alkaline earth metal, and ammonium salts of polystyrenesulfonic acids, salts of polyvinylsulfonic acids, salts of alkylnaphthalenesulfonic acids, salts of alkylnaphthalenesulfonic acid-formaldehyde condensation products, and salts of condensation products of naphthalenesulfonic acid, phenolsulfonic acid, and formaldehyde. Examples include calcium dodecylbenzenesulfonate such as Rhodocal® < 70 / B (Solvay), phenylsulfonate CA100 (Clariant), and isopropylammonium dodecylbenzenesulfonates such as Atlox® < 3300B (Croda).
[0038] Other typical examples include Soprophor®< types (possibly esterified derivatives of tristyrylphenoi ethoxylates), Emulsogen®< 3510 (alkylated EO / PO copolymer), Emulsogen®< EL 400 (ethoxylated castor oil), Tween®< types (fatty acylated sorbitan ethoxylates), Calsogen®< AR 100 (Ca-dodecylbenzenesulfonate). Preferred are combinations of salts of alkylated aromatic sulfonic acids, such as phenylsulfonate Ca and / or Calsogen®< AR 100, with alkylated copolymers of ethylene and propylene oxide, such as Emulsogen®< 3510. Particularly preferred are combinations of salts of dodecylbenzenesulfonic acid, such as Calsogen®< AR 100, with alkylated copolymers of ethylene and propylene oxide, such as Emulsogen®< 3510.
[0039] Examples of other anionic emulsifiers b) from the naphthalenesulfonate group are Galoryl ®< MT 800 (sodium dibutylnaphthalenesulfonic acid), Morwet ®< IP (sodium diisopropylnaphthalenesulfonate) and Nekal ®< BX (alkylnaphthalenesulfonate). Examples of anionic surfactants from the group of condensation products of naphthalenesulfonates with formaldehyde are Galoryl®< DT 201 (naphthalenesulfonic acid hydroxypolymer with formaldehyde and methylphenol sodium salt), Galoryl®< DT 250 (condensation product of phenol and naphthalenesulfonates), Reserve®< C (condensation product of phenol and naphthalenesulfonates), or Morwet®< D-425, Tersperse®< 2020. Preferably, naphthalenesulfonates 1,2-substituted with dibutyl or di-isobutyl are used, such as products like Galoryl®< MT 800 (CFPI-Nufarm) and Nekal®< BX (BASF).Other typical surfactants are Soprophor®< 3D33, Soprophor®< 4D384, Soprophor®< BSU, Soprophor®< CY / 8 (Solvay) and Hoe®< S3474 and in the form of the Sapogenat®< T products (Clariant), for example Sapogenat®< T 100. Other typical examples are based on lignin (such as lignosulfonates, Borresperse®< NA, REAX®< 88 or Kraftsperse®< 25 S).
[0040] Of the above-mentioned anionic dispersing agents b), various sulfonates are preferably used, especially those based on naphthalene.
[0041] Suitable nonionic dispersants (b) such as emulsifiers, wetting agents, surfactants, and dispersants are common surface-native substances found in formulations of agrochemical active ingredients. Examples include ethoxylated nonylphenols, reaction products of linear or branched alcohols with ethylene oxide and / or propylene oxide, ethylene oxide-propylene oxide block copolymers, and end-capped and non-end-capped alkoxylated linear and branched, saturated and unsaturated alcohols (e.g.,Butoxypolyethylenepropylene glycols), reaction products of alkylphenols with ethylene oxide and / or propylene oxide, ethylene oxide-propylene oxide block copolymers, polyethylene glycols and polypropylene glycols, furthermore fatty acid esters, fatty acid polyglycol ether esters, alkyl sulfonates, alkyl sulfates, aryl sulfates, ethoxylated arylalkylphenols, such as tristyrylphenol ethoxylate with an average of 16 ethylene oxide units per molecule, furthermore ethoxylated and propoxylated arylalkylphenols as well as sulfated or phosphatized arylalkylphenol ethoxylates or -ethoxy- and -propoxylates. Tristyrylphenol alkoxylates and fatty acid polyglycol ether esters are particularly preferred. Tristyrylphenol ethoxylates, tristyrylphenol ethoxy-propoxylates and castor oil polyglycol ether esters, each individually or in mixtures, are especially preferred. In addition, additives such as surfactants or fatty acid esters may be used to improve biological efficacy.Suitable non-ionic emulsifiers b2) are, for example, Soprophor ®< 796 / P, Lucramul ®< CO 30, Lucramul ®< HOT 5902, Lucramul ®< PSI 100 or Synperonic ®< T304.
[0042] Suitable non-ionic dispersants (b) may also be selected from the group containing polyvinylpyrrolidone (PVP), polyvinyl alcohol, PVP-dimethylaminoethyl methacrylate copolymer, butylated PVP, vinyl chloride-vinyl acetate copolymer, and partially hydrolyzed vinyl acetate, phenolic resins, modified cellulose types such as Luviskol® (polyvinylpyrrolidone), Mowiol® (polyvinyl alcohol), or modified cellulose. Polyvinylpyrrolidone types are preferred, and low molecular weight types such as Luviskol® K30 or Sokalan® K30 are particularly preferred.
[0043] Other non-ionic emulsifiers (b) that are preferably used, from the group of di- and tri-block copolymers of alkylene oxides, include, for example, compounds based on ethylene and propylene oxides, with average molar masses between 200 and 10,000, preferably 1,000 to 4,000 g / mol, wherein the mass fraction of the polyethoxylated block varies between 10 and 80%, such as Synperonic®< PE series (CRODA), Pluronic®< PE series (BASF), VOP®< 32 or Genapol®< PF series (Clariant). Unless otherwise specified, the molar masses are determined by GPC using chloroform as the mobile phase and polystyrene as the standard.
[0044] A combination of at least one ionic and one non-ionic dispersing agent is particularly preferred.
[0045] Component c) relates to the group comprising organically modified (poly)-glycosides, organically modified furanoses, organically modified pyranoses, and organically modified sorbitans and sorbitols, as well as mixtures thereof.
[0046] The group of organically modified (poly)-glycosides further preferably includes non-ionic alkyl polysaccharides (e.g. alkyl polyglucosides or APG).
[0047] According to the invention, component c) is an alkyl polysaccharide.
[0048] Suitable alkyl polysaccharides according to the present invention have a structure according to formula (I): R 5< -O-( su g) u (I), wherein R5 is an unbranched or branched, optionally substituted or unsubstituted, hydrocarbyl group selected from the group consisting of alkyl, alkenyl, alkylphenyl and alkenylphenyl, preferably with 4 to 22 carbon atoms. It is known to those skilled in the art that alkenylphenyl and alkylphenyl must contain at least 7 carbon atoms.
[0049] The su g unit is a saccharide residue with an open or cyclic (i.e., pyranose / furanose) structure. The saccharide residue is preferably selected from the group comprising monosaccharides, more preferably monosaccharides with 5 or 6 carbon atoms, disaccharides, and polysaccharides. Suitable saccharide residues according to the invention, including their corresponding pyranose or furanose structures, preferably include ribose, xylose, arabinose, glucose, galactose, mannose, telose, gulose, allose, altrose, idose, lyxose, ribulose, sorbose (sorbitan), fructose, and mixtures thereof.
[0050] According to the invention, suitable disaccharide residues preferably comprise maltose, lactose and sucrose.
[0051] Disaccharides, oligosaccharides and polysaccharides can be a composition of two or more identical saccharides, such as maltose, which is made up of two glucose units, or two or more different saccharides, such as sucrose, which is composed of glucose and fructose.
[0052] The degree of polymerization of oligo- and polysaccharides, u, is an average value preferably from 1 to 10, more preferably from 1 to 8, even more preferably from 1 to 5, even more preferably from 1 to 3, and particularly preferably from 1 to 2.
[0053] As is known to those skilled in the art, and as shown in formula (I), the residue R 5< is bonded to an oxygen atom of the sug unit.
[0054] In a preferred embodiment, the alkyl polysaccharide can be an alkyl polyglycoside (APG) of formula (I), wherein R5 is an unbranched or branched alkyl group with preferably 4 to 22 carbon atoms, more preferably 8 to 18 carbon atoms, and even more preferably 8 to 10 carbon atoms, or a mixture of alkyl groups with an average number of carbon atoms in the aforementioned ranges; and wherein su g is preferably a glucuso group (e.g., a glucoside), and wherein u is preferably in the range of 1 to 5, particularly preferably from 1 to 3.
[0055] In a further preferred embodiment, the alkyl polysaccharide is an alkyl polyglycoside (APG) of formula (I), wherein R5 is an unbranched or branched alkyl group with preferably 8 to 10 carbon atoms, or a mixture of alkyl groups with an average number of carbon atoms in the previously given ranges; and wherein su g is preferably a glucuso group (e.g. a glucoside), and wherein u is in the range of 1 to 3.
[0056] Examples of alkyl polysaccharides according to formula (I) according to the invention are known to those skilled in the art and preferred compounds of this type are listed below, wherein sug according to formula (I) is glucose in these compounds: : AGNIQUE ®< PG8107-G, AGNIQUE ®< PG 8107-U, AGNIQUE ®< PG 9116, AGNIQUE ®< PG 8105 U, AGNIQUE ®< PG 8105 G, AGNIQUE PG ®< 8105 C (all available from BASF).
[0057] Alternatively, but not according to the invention, component c) is selected from the group comprising the organically modified sorbitans and / or sorbitols.
[0058] An example of an alkoxylated polysorbate ester according to formula (II) has the following structure: R1, R2, and R3 are fatty acid residues or a hydroxyl group, wherein the fatty acid is preferably a C10 to C20 fatty acid, more preferably a C12 to C18 fatty acid, and particularly preferably selected from the group comprising oleic acid, stearic acid, and lauric acid. The substituents R1 to R3 can be the same or different.
[0059] Representatives of this class are listed below, with Tween 80 being particularly preferred. Tween 85: R1=R2=R3 = Oleic acid Tween 80: R1=R2= OH; R3 = Oleic acid Tween 60: R1=R2= OH; R3 = Stearic acid Tween 20: R1=R2= OH; R3 = Lauric acid
[0060] For example, the structure of Tween® < 80: w, x, y and z are integers, preferably from 0 to 20, preferably 0 to 15, more preferably 0 to 10, where 0 corresponds to an OH group.
[0061] Alternatively, all or some EO units (ethylene oxide as shown in formula II) can be replaced by PO (propylene oxide), e.g. Tween ®< L-1505 (from CRODA) with 15 EO and 5 PO units.
[0062] Examples of adjuvants of structure (II) are known to those skilled in the art; the corresponding commercial products are listed below: product Mol EO Mol PO Log P Tween 21 4 0 2.71 Tween 22 8 0 1.90 Tween 23 12 0 1.08 Tween 24 16 0 0.26 Tween 20 20 0 -0.55 Tween 80 20 0 1.99 Tween 60 20 0 2.48 Tween 40 20 0 1.47 Tween L-0515 5 15 7.44 Tween L-1010 10 10 4.68 Tween L-1505 15 5 1.92
[0063] Alternatively, Tween®< 80 and Tween®< L-1505 can be mentioned.
[0064] Alternatively, but not according to the invention, c) can be selected from the group of organically modified (poly)-glycosides.
[0065] Alternatively, but not according to the invention, c) can be selected from the group of alkoxylated polysorbate esters according to formula (II).
[0066] Particularly preferably, the adjuvant c) further exhibits a LogP in the range of 0 to 8, more preferably from 0.1 to 5, and particularly preferably from 0.5 to 4.0.
[0067] A logP value ± 2 units higher or lower than the logP value of active ingredient a) is particularly preferred. Agrochemical active ingredients (component d) that differ from component a) are herbicides, fungicides, insecticides, plant growth regulators, and the like.
[0068] Fungizide Wirkstoffe sind z.B. 1) Inhibitoren der Ergosterol-Biosynthese, beispielsweise (1.001) Cyproconazol, (1.002) Difenoconazol, (1.003) Epoxiconazol, (1.004) Fenhexamid, (1.005) Fenpropidin, (1.006) Fenpropimorph, (1.007) Fenpyrazamin, (1.008) Fluquinconazol, (1.009) Flutriafol, (1.010) Imazalil, (1.011) Imazalil Sulfat, (1.012) Ipconazol, (1.013) Metconazol, (1.014) Myclobutanil, (1.015) Paclobutrazol, (1.016) Prochloraz, (1.017) Propiconazol, (1.018) Prothioconazol, (1.019) Pyrisoxazol, (1.020) Spiroxamin, (1.021) Tebuconazol, (1.022) Tetraconazol, (1.023) Triadimenol, (1.024) Tridemorph, (1.025) Triticonazol, (1.026) (1R,2S,5S)-5-(4-Chlorbenzyl)-2-(chlormethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.027) (1S,2R,5R)-5-(4-Chlorbenzyl)-2-(chlormethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.028) (2R)-2-(1-Chlorcyclopropyl)-4-[(1R)-2,2-dichlorcyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol (1.029) (2R)-2-(1-Chlorcyclopropyl)-4-[(1S)-2,2-dichlorcyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.030) (2R)-2-[4-(4-Chlorphenoxy)-2-(trifluormethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.031) (2S)-2-(1-Chlorcyclopropyl)-4-[(1R)-2,2-dichlorcyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.032) (2S)-2-(1-Chlorcyclopropyl)-4-[(1S)-2,2-dichlorcyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.033) (2S)-2-[4-(4-Chlorphenoxy)-2-(trifluormethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.034) (R)-[3-(4-Chlor-2-fluorphenyl)-5-(2,4-difluorphenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.035) (S)-[3-(4-Chlor-2-fluorphenyl)-5-(2,4-difluorphenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.036) [3-(4-Chlor-2-fluorphenyl)-5-(2,4-difluorphenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.037) 1-({(2R,4S)-2-[2-Chlor-4-(4-chlorphenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazol, (1.038) 1-({(2S,4S)-2-[2-Chlor-4-(4-chlorphenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazol, (1.039) 1-{[3-(2-Chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl-thiocyanat, (1.040) 1-{[rel(2R,3R)-3-(2-Chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl-thiocyanat, (1.041) 1-{[rel(2R,3S)-3-(2-Chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl-thiocyanat, (1.042) 2-[(2R,4R,5R)-1-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.043) 2-[(2R,4R,5S)-1-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.044) 2-[(2R,4S,5R)-1-(2,4-Dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.045) 2-[(2R,4S,5S)-1-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.046) 2-[(2S,4R,5R)-1-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.047) 2-[(2S,4R,5S)-1-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.048) 2-[(2S,4S,5R)-1-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.049) 2-[(2S,4S,5S)-1-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.050) 2-[1-(2,4-Dichlorphenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.051) 2-[2-Chlor-4-(2,4-dichlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.052) 2-[2-Chlor-4-(4-chlorphenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.053) 2-[4-(4-Chlorphenoxy)-2-(trifluormethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.054) 2-[4-(4-Chlorphenoxy)-2-(trifluormethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)pentan-2-ol, (1.055) 2-[4-(4-Chlorphenoxy)-2-(trifluormethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.056) 2-{[3-(2-Chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.057) 2-{[rel(2R,3R)-3-(2-Chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.058) 2-{[rel(2R,3S)-3-(2-Chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl] methyl}-2,4-dihydro-3H-1,2,4-triazol-3-thion, (1.059) 5-(4-Chlorbenzyl)-2-(chlormethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.060) 5-(Allylsulfanyl)-1-{[3-(2-chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol, (1.061) 5-(Allylsulfanyl)-1-{[rel(2R,3R)-3-(2-chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol, (1.062) 5-(Allylsulfanyl)-1-{[rel(2R,3S)-3-(2-chlorphenyl)-2-(2,4-difluorphenyl)oxiran-2-yl]methyl]-1H-1,2,4-triazol, (1.063) N'-(2,5-Dimethyl-4-{[3-(1,1,2,2-tetrafluorethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamid, (1.064) N'-(2,5-Dimethyl-4-{[3-(2,2,2-trifluorethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamid, (1.065) N'-(2,5-Dimethyl-4-{[3-(2,2,3,3-tetrafluorpropoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamid, (1.066) N'-(2,5-Dimethyl-4-{[3-(pentafluorethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamid, (1.067) N'-(2,5-Dimethyl-4-{3-[(1,1,2,2-tetrafluorethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamid, (1.068) N'-(2,5-Dimethyl-4-{3-[(2,2,2-trifluorethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamid, (1.069) N'-(2,5-Dimethyl-4-{3-[(2,2,3,3-tetrafluorpropyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamid, (1.070) N'-(2,5-Dimethyl-4-{3-[(pentafluorethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamid, (1.071) N'-(2,5-Dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoformamid, (1.072) N'-(4-{[3-(Difluormethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamid, (1.073) N'-(4-{3-[(Difluormethyl)sulfanyl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamid, (1.074) N'-[5-Brom-6-(2,3-dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimidoformamid, (1.075) N'-{4-[(4,5-Dichlor-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamid, (1.076) N'-{5-Brom-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamid, (1.077) N'-{5-Brom-6-[(1S)-1-(3,5-difluorphenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamid, (1.078) N'-{5-Brom-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamid, (1.079) N'-{5-Brom-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamid, (1.080) N'-{5-Bromo-6-[1-(3,5-difluorphenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamid, (1.081) Mefentrifluconazole, (1.082) Ipfentrifluconazole.
[0069] 2) Inhibitoren der Atmungskette am Komplex I oder II for example (2.001) Benzovindiflupyr, (2.002) Bixafen, (2.003) Boscalid, (2.004) Carboxin, (2.005) Fluopyram, (2.006) Flutolanil, (2.007) Fluxapyroxad, (2.008) Furametpyr, (2.009) Isofetamid, (2.010) Isopyrazam (anti-epimers Enantiomer 1R,4S,9S), (2.011) Isopyrazam (anti-epimers Enantiomer 1S,4R,9R), (2.012) Isopyrazam (anti-epimers Racemat 1RS,4SR,9SR), (2.013) Isopyrazam (Mischung des syn-epimeren Racemates 1RS,4SR,9RS und des antiepimeren Racemates 1RS,4SR,9SR), (2.014) Isopyrazam (syn-epimeres Enantiomer 1R,4S,9R), (2.015) Isopyrazam (syn-epimeres Enantiomer 1S,4R,9S), (2.016) Isopyrazam (syn-epimeres Racemat 1RS,4SR,9RS), (2.017) Penflufen, (2.018) Penthiopyrad, (2.019) Pydiflumetofen, (2.020) Pyraziflumid, (2.021) Sedaxane, (2.022) 1,3-Dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazol-4-carboxamid, (2.023) 1,3-Dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.024) 1,3-Dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazol-4-carboxamid, (2.025) 1-Methyl-3-(trifluormethyl)-N-[2'-(trifluormethyl)biphenyl-2-yl]-1H-pyrazol-4-carboxamid, (2.026) 2-Fluor-6-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)benzamid, (2.027) 3-(Difluormethyl)-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazol-4-carboxamid, (2.028) 3-(Difluormethyl)-1-methyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazol-4-carboxamid, (2.029) 3-(Difluormethyl)-1-methyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazol-4-carboxamid, (2.030) 3-(Difluormethyl)-N-(7-fluor-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1-methyl-1H-pyrazol-4-carboxamid, (2.031) 3-(Difluormethyl)-N-[(3R)-7-fluor-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazol-4-carboxamid, (2.032) 3-(Difluoromethyl)-N-[(3S)-7-fluor-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazol-4-carboxamid, (2.033) 5,8-Difluor-N-[2-(2-fluor-4-{[4-(trifluormethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazolin-4-amin, (2.034) N-(2-Cyclopentyl-5-fluorbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor-1-methyl-1H-pyrazol-4-carboxamid, (2.035) N-(2-tert-Butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor-1-methyl-1H-pyrazol-4-carboxamid, (2.036) N-(2-tert-Butylbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor-1-methyl-1H-pyrazol-4-carboxamid, (2.037) N-(5-Chlor-2-ethylbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor-1-methyl-1H-pyrazol-4-carboxamid, (2.038) N-(5-Chlor-2-isopropylbenzyl)-N-cyclopropyl-3-(difluormethyl)-5-fluor-1-methyl-1H-pyrazol-4-carboxamid, (2.039) N-[(1R,4S)-9-(Dichlormethylen)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluormethyl)-1-methyl-1H-pyrazol-4-carboxamid, (2.040) N-[(1S,4R)-9-(Dichlormethylen)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluormethyl)-1-methyl-1H-pyrazol-4-carboxamid, (2.041) N-[1-(2,4-Dichlorphenyl)-1-methoxypropan-2-yl]-3-(difluormethyl)-1-methyl-1H-pyrazol-4-carboxamid, (2.042) N-[2-Chlor-6-(trifluormethyl)benzyl]-N-cyclopropyl-3-(difluormethyl)-5-fluor-1-methyl-1H-pyrazol-4-carboxamid, (2.043) N-[3-Chlor-2-fluor-6-(trifluormethyl)benzyl]-N-cyclopropyl-3-(difluormethyl)-5-fluor-1-methyl-1H-pyrazol-4-carboxamid, (2.044) N-[5-Chlor-2-(trifluormethyl)benzyl]-N-cyclopropyl-3-(difluormethyl)-5-fluor-1-methyl-1H-pyrazol-4-carboxamid, (2.045) N-Cyclopropyl-3-(difluormethyl)-5-fluor-1-methyl-N-[5-methyl-2-(trifluormethyl)benzyl]-1H-pyrazol-4-carboxamid, (2.046) N-Cyclopropyl-3-(difluormethyl)-5-fluor-N-(2-fluor-6-isopropylbenzyl)-1-methyl-1H-pyrazol-4-carboxamid, (2.047) N-Cyclopropyl-3-(difluormethyl)-5-fluor-N-(2-isopropyl-5-methylbenzyl)-1-methyl-1H-pyrazol-4-carboxamid, (2.048) N-Cyclopropyl-3-(difluormethyl)-5-fluor-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazol-4-carbothioamid, (2.049) N-Cyclopropyl-3-(difluoromethyl)-5-fluor-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazol-4-carboxamid, (2.050) N-Cyclopropyl-3-(difluormethyl)-5-fluor-N-(5-fluor-2-isopropylbenzyl)-1-methyl-1H-pyrazol-4-carboxamid, (2.051) N-Cyclopropyl-3-(difluormethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluor-1-methyl-1H-pyrazol-4-carboxamid, (2.052) N-Cyclopropyl-3-(difluormethyl)-N-(2-ethyl-5-fluorbenzyl)-5-fluor-1-methyl-1H-pyrazol-4-carboxamid, (2.053) N-Cyclopropyl-3-(difluormethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluor-1-methyl-1H-pyrazole-4-carboxamid, (2.054) N-Cyclopropyl-N-(2-cyclopropyl-5-fluorbenzyl)-3-(difluormethyl)-5-fluor-1-methyl-1H-pyrazole-4-carboxamid, (2.055) N-Cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluormethyl)-5-fluor-1-methyl-1H-pyrazole-4-carboxamid, (2.056) N-Cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluormethyl)-5-fluor-1-methyl-1H-pyrazole-4-carboxamid.
[0070] 3) Inhibitoren der Atmungskette am Komplex III, beispielsweise (3.001) Ametoctradin, (3.002) Amisulbrom, (3.003) Azoxystrobin, (3.004) Coumethoxystrobin, (3.005) Coumoxystrobin, (3.006) Cyazofamid, (3.007) Dimoxystrobin, (3.008) Enoxastrobin, (3.009) Famoxadon, (3.010) Fenamidon, (3.011) Flufenoxystrobin, (3.012) Fluoxastrobin, (3.013) Kresoxim-Methyl, (3.014) Metominostrobin, (3.015) Orysastrobin, (3.016) Picoxystrobin, (3.017) Pyraclostrobin, (3.018) Pyrametostrobin, (3.019) Pyraoxystrobin, (3.020) Trifloxystrobin (3.021) (2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-Fluor-2-phenylvinyl]oxy}phenyl)ethyliden]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamid, (3.022) (2E,3Z)-5-{[1-(4-Chlorphenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamid, (3.023) (2R)-2-{2-[(2,5-Dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamid, (3.024) (2S)-2-{2-[(2,5-Dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamid, (3.025) (3S,6S,7R,8R)-8-Benzyl-3-[({3-[(isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl-2-methylpropanoat, (3.026) 2-{2-[(2,5-Dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamid, (3.027) N-(3-Ethyl-3,5,5-trimethylcyclohexyl)-3-formamido-2-hydroxybenzamid, (3.028) (2E,3Z)-5-{[1-(4-Chlor-2-fluorphenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamid, (3.029) Methyl {5-[3-(2,4-dimethylphenyl)-1H-pyrazol-1-yl]-2-methylbenzyl}carbamate.
[0071] 4) Inhibitoren der Mitose und Zellteilung, beispielsweise (4.001) Carbendazim, (4.002) Diethofencarb, (4.003) Ethaboxam, (4.004) Fluopicolid, (4.005) Pencycuron, (4.006) Thiabendazol, (4.007) Thiophanat-Methyl, (4.008) Zoxamid, (4.009) 3-Chlor-4-(2,6-difluorphenyl)-6-methyl-5-phenylpyridazin, (4.010) 3-Chlor-5-(4-chlorphenyl)-4-(2,6-difluorphenyl)-6-methylpyridazin, (4.011) 3-Chlor-5-(6-chlorpyridin-3-yl)-6-methyl-4-(2,4,6-trifluorphenyl)pyridazin, (4.012) 4-(2-Brom-4-fluorphenyl)-N-(2,6-difluorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (4.013) 4-(2-Brom-4-fluorphenyl)-N-(2-brom-6-fluorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (4.014) 4-(2-Brom-4-fluorphenyl)-N-(2-bromphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (4.015) 4-(2-Brom-4-fluorphenyl)-N-(2-chlor-6-fluorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (4.016) 4-(2-Brom-4-fluorphenyl)-N-(2-chlorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (4.017) 4-(2-Brom-4-fluorphenyl)-N-(2-fluorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (4.018) 4-(2-Chlor-4-fluorphenyl)-N-(2,6-difluorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (4.019) 4-(2-Chlor-4-fluorphenyl)-N-(2-chlor-6-fluorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (4.020) 4-(2-Chlor-4-fluorphenyl)-N-(2-chlorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (4.021) 4-(2-Chlor-4-fluorphenyl)-N-(2-fluorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (4.022) 4-(4-Chlorphenyl)-5-(2,6-difluorphenyl)-3,6-dimethylpyridazin, (4.023) N-(2-Brom-6-fluorphenyl)-4-(2-chlor-4-fluorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (4.024) N-(2-Bromphenyl)-4-(2-chlor-4-fluorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin, (4.025) N-(4-Chlor-2,6-difluorphenyl)-4-(2-chlor-4-fluorphenyl)-1,3-dimethyl-1H-pyrazol-5-amin.
[0072] 5) Compounds capable of multisite activity, for example (5.001) Bordeaux mixture, (5.002) Captafol, (5.003) Captan, (5.004) Chlorothalonil, (5.005) Copper hydroxide, (5.006) Copper naphthenate, (5.007) Copper oxide, (5.008) Copper oxychloride, (5.009) Copper(2+) sulfate, (5.010) Dithianon, (5.011) Dodine, (5.012) Folpet, (5.013) Mancozeb, (5.014) Maneb, (5.015) Metiram, (5.016) Zinc metiram, (5.017) Copper oxine, (5.018) Propineb, (5.019) Sulfur and sulfur preparations including calcium polysulfide, (5.020) Thiram, (5,021) Zineb, (5,022) Ziram, (5,023) 6-Ethyl-5,7-dioxo-6,7-dihydro-5H-pyrrolo[3',4':5,6][1,4]dithiino[2,3-c][1,2]thiazole-3-carbonitrile.
[0073] 6) Compounds capable of triggering host defense, for example (6.001) Acibenzolar-S-Methyl, (6.002) Isotianil, (6.003) Probenazol, (6.004) Tiadinil.
[0074] 7) Inhibitors of amino acid and / or protein biosynthesis, for example (7.001) cyprodinil, (7.002) kasugamycin, (7.003) kasugamycin hydrochloride hydrate, (7.004) oxytetracycline, (7.005) pyrimethanil, (7.006) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinoline-1-yl)quinoline.
[0075] (8) Inhibitors of ATP production, for example (8.001) Silthiofam.
[0076] 9) Inhibitors of cell wall synthesis, for example (9.001) Benthiavalicarb, (9.002) Dimethomorph, (9.003) Flumorph, (9.004) Iprovalicarb, (9.005) Mandipropamid, (9.006) Pyrimorph, (9.007) Valifenalate, (9.008) (2E)-3-(4-tert-Butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one, (9.009) (2Z)-3-(4-tert-Butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one.
[0077] 10) Inhibitors of lipid and membrane synthesis, for example (10.001) Propamocarb, (10.002) Propamocarb hydrochloride, (10.003) Tolclofos methyl.
[0078] 11) Inhibitors of melanin biosynthesis, for example (11.001) tricyclazole, (11.002) 2,2,2-trifluoroethyl-{3-methyl-1-[(4-methylbenzoyl)amino]butan-2-yl}carbamate.
[0079] 12) Nucleic acid synthesis inhibitors, for example (12.001) Benalaxyl, (12.002) Benalaxyl-M (Kiralaxyl), (12.003) Metalaxyl, (12.004) Metalaxyl-M (Mefenoxam).
[0080] 13) Inhibitors of signal transduction, for example (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazide, (13.005) quinoxyfen, (13.006) vinclozoline.
[0081] 14) Compounds that can act as uncouplers, for example (14.001) Fluazinam, (14.002) Meptyldinocap.
[0082] 15) Other compounds, for example (15.001) abscisic acid, (15.002) benthiazole, (15.003) bethoxazine, (15.004) capsimycin, (15.005) carvone, (15.006) quinomethionate, (15.007) cufraneb, (15.008) cyflufenamide, (15.009) cymoxanil, (15.010) cyprosulfamide, (15.011) flutianil, (15.012) fosetyl aluminum, (15.013) fosetyl calcium, (15.014) fosetyl sodium, (15.015) methyl isothiocyanate, (15.016) metrafenone, (15.017) mildiomycin, (15.018) Natamycin, (15.019) Nickel dimethyldithiocarbamate, (15.020) Nitrothal isopropyl, (15.021) Oxamocarb, (15.022) Oxathiapiproline, (15.023) Oxyfenthiin, (15.024) Pentachlorophenol and salts, (15.025) Phosphonic acid and its salts, (15.026) Propamocarb fosetylate, (15.027) Pyriofenones (Chlazafenones), (15.028) Tebufloquine, (15.029) Tecloftalam, (15.030) Tolnifanides, (15.031) 1-(4-{4-[(5R)-5-(2,6-Difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone, (15.032) 1-(4-{4-[(5S)-5-(2,6-Difluorphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluormethyl)-1H-pyrazol-1-yl]ethanon, (15.033) 2-(6-Benzylpyridin-2-yl)quinazolin, (15.034) 2,6-Dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrol-1,3,5,7(2H,6H)-tetron, (15.035) 2-[3,5-Bis(difluormethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-(prop-2-in-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanon, (15.036) 2-[3,5-Bis(difluormethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-chlor-6-(prop-2-in-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanon, (15.037) 2-[3,5-Bis(difluormethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-fluor-6-(prop-2-in-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanon, (15.038) 2-[6-(3-Fluor-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazolin, (15.039) 2-{(5R)-3-[2-(1-{[3,5-Bis(difluormethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorphenyl methanesulfonat, (15.040) 2-{(5S)-3-[2-(1-{[3,5-Bis(difluormethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorphenyl methanesulfonat, (15.041) 2-{2-[(7,8-Difluor-2-methylquinolin-3-yl)oxy]-6-fluorphenyl}propan-2-ol, (15.042) 2-{2-Fluor-6-[(8-fluor-2-methylquinolin-3-yl)oxy]phenyl}propan-2-ol, (15.043) 2-{3-[2-(1-{[3,5-Bis(difluormethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorphenyl-methansulfonat, (15.044) 2-{3-[2-(1-{[3,5-Bis(difluormethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl methanesulfonat, (15.045) 2-Phenylphenol und deren Salze, (15.046) 3-(4,4,5-Trifluor-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinolin, (15.047) 3-(4,4-Difluor-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinolin, (15.048) 4-Amino-5-fluorpyrimidin-2-ol (Tautomere Form: 4-Amino-5-fluorpyrimidin-2(1H)-on), (15.049) 4-Oxo-4-[(2-phenylethyl)amino]buttersäure, (15.050) 5-Amino-1,3,4-thiadiazol-2-thiol, (15.051) 5-Chlor-N'-phenyl-N'-(prop-2-yn-1-yl)thiophen-2-sulfonohydrazid, (15.052) 5-Fluor-2-[(4-fluorbenzyl)oxy]pyrimidin-4-amin, (15.053) 5-Fluor-2-[(4-methylbenzyl)oxy]pyrimidin-4-amin, (15.054) 9-Fluor-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro-1,4-benzoxazepin, (15.055) But-3-yn-1-yl {6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylen]amino}oxy)methyl]pyridin-2-yl}carbamat, (15.056) Ethyl (2Z)-3-amino-2-cyano-3-phenylacrylat, (15.057) Phenazin-1-carbonsäure, (15.058) Propyl 3,4,5-trihydroxybenzoat, (15.059) Quinolin-8-ol, (15.060) Quinolin-8-ol sulfat (2:1), (15.061) tert-Butyl {6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino]oxy)methyl]pyridin-2-yl]carbamat, (15.062) 5-Fluor-4-imino-3-methyl-1-[(4-methylphenyl)sulfonyl]-3,4-dihydropyrimidin-2(1H)-one. Insecticidal active ingredients include, for example: . (1) Acetylcholinesterase (AChE) Inhibitoren, wie beispielsweise Carbamate, z.B. Alanycarb, Aldicarb, Bendiocarb, Benfuracarb, Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan, Ethiofencarb, Fenobucarb, Formetanate, Furathiocarb, Isoprocarb, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Propoxur, Thiodicarb, Thiofanox, Triazamate, Trimethacarb, XMC und Xylylcarb oder organophosphate, z.B.Acephate, Azamethiphos, Azinphos-ethyl, Azinphos-methyl, Cadusafos, Chlorethoxyfos, Chlorfenvinphos, Chlormephos, Chlorpyrifos, Chlorpyrifos-methyl, Coumaphos, Cyanophos, Demeton-S-methyl, Diazinon, Dichlorvos / DDVP, Dicrotophos, Dimethoate, Dimethylvinphos, Disulfoton, EPN, Ethion, Ethoprophos, Famphur, Fenamiphos, Fenitrothion, Fenthion, Fosthiazate, Heptenophos, Imicyafos, Isofenphos, Isopropyl O-(methoxyaminothio-phosphoryl) salicylat, Isoxathion, Malathion, Mecarbam, Methamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion, Parathion-methyl, Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimiphos-methyl, Profenofos, Propetamphos, Prothiofos, Pyraclofos, Pyridaphenthion, Quinalphos, Sulfotep, Tebupirimfos, Temephos, Terbufos, Tetrachlorvinphos, Thiometon, Triazophos, Triclorfon und Vamidothion. (2) GABA-gesteuerte Chlorid-Kanal-Antagonisten, wie beispielsweise Cyclodien-organochlorine, z.B.Chlordanes and endosulfan or phenylpyrazoles (fiprols), e.g. ethiprol and fipronil. (3) Sodium channel modulators / voltage-dependent sodium channel blockers, such as pyrethroids, e.g. acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(1R)-trans isomers], deltamethrin, empenthrin [(EZ)-(1R) isomers), esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-Fluvalinate, Halfenprox, Imiprothrin, Kadethrin, Momfluorothrin, Permethrin, Phenothrin [(1R)-trans-Isomer), Prallethrin, Pyrethrins (pyrethrum), Resmethrin, Silafluofen, Tefluthrin, Tetramethrin, Tetramethrin [(1R)-Isomers)], Tralomethrin and Transfluthrin or DDT or Methoxychlor.(4) Nicotinic acetylcholine receptor (nAChR) agonists, such as neonicotinoids, e.g., acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, and thiamethoxam, or nicotine, or sulfoxaflor, or flupyradifurone. (5) Nicotinic acetylcholine receptor (nAChR) allosteric activators, such as spinosins, e.g., spinetoram and spinosad. (6) Chloride channel activators, such as avermectins / milbemycins, e.g., abamectin, emamectin benzoate, lepimectin, and milbemectin. (7) Juvenile hormone mimics, such as juvenile hormone analogs, e.g., hydroprene, kinoprene, and methoprene, or fenoxycarb or pyriproxyfen. (8) Active substances with unknown or non-specific mechanisms of action, such as alkyl halides, e.g., methyl bromide and other alkyl halides; or chloropicrin or sulfuryl fluoride or borax or tartar emetic. (9) Selective feeding deterrents, e.g., pymetrozine or flonicamide. (10) Mite growth inhibitors, e.g.Clofentezine, hexythiazox and diflovidazine or etoxazoles. (11) Microbial disruptors of the insect intestinal membrane, e.g. Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis and BT plant proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34 / 35Ab1. (12) Inhibitors of oxidative phosphorylation, ATP disruptors, such as diafenthiuron or organotin compounds, e.g. azocyclotin, cyhexatine and fenbutatin oxide or propargite or tetradifone. (13) Uncouplers of oxidative phosphorylation by interrupting the H-proton gradient, such as chlorfenapyr, DNOC, and sulfuramide. (14) Nicotinic acetylcholine receptor antagonists, such as Bensultap, Cartap hydrochloride, thiocyclam, and thiosultap sodium.(15) Type 0 chitin biosynthesis inhibitors, such as bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumurone, lufenuron, novaluron, noviflumurone, teflubenzuron, and triflumurone. (16) Type 1 chitin biosynthesis inhibitors, such as buprofezin. (17) Molting inhibitors, dipterans, such as cyromazine. (18) Ecdysone receptor agonists, such as chromafenozides, halofenozides, methoxyfenozides, and tebufenozides. (19) Octomatergic agonists, such as amitraz. (20) Complex III electron transport inhibitors, such as hydramethylnone, acequinocyl, or fluacrypyrim. (21) Complex I electron transport inhibitors, for example METI acaricides, e.g. fenazaquin, fenpyroximates, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad or rotenones (Derris). (22) Voltage-gated sodium channel blockers, e.g. indoxacarb or metaflumizone.(23) Acetyl-CoA carboxylase inhibitors, such as tetronic and tetramic acid derivatives, e.g., spirobudiclofen, spirodiclofen, spiromesifen, and spirotetramate. (24) Complex IV electron transport inhibitors, such as phosphines, e.g., aluminum phosphide, calcium phosphide, phosphine, and zinc phosphide, or cyanide. (25) Complex II electron transport inhibitors, such as cyenopyrafen and cyflumetofen. (28) Ryanodine receptor effectors, such as diamides, e.g., chloroantraniliproles, cyantraniliproles, flubendiamides, and tetrachloroantraniliproles.
[0083] Other insecticidal active ingredients with unknown or unclear mechanisms of action, such as afidopyropene, afoxolaner, azadirachtin, benclothiaz, benzoximates, bifenazates, broflanilides, bromopropylates, quinomethionate, cryolite, cyclaniliproles, cycloxaprid, cyhalodiamides, dicloromezotiaz, dicofol, diflovidazine, flometoquine, fluazaindolizine, fluensulfone, flufenerim, flufenoxystrobin, flufiproles, fluhexafone, fluopyram, fluralaner, fluxametamide, fufenozide, guadipyr, heptafluthrin, imidaclothiz, iprodione, lotilaner, meperfluthrin, paichongding, pyflubumide, pyridalyl, pyrifluquinazone, pyriminostrobin, sarolaner, and tetramethylfluthrin. Tetraniliprole, tetrachloroantraniliprole, tioxazafen, thiofluoximate, triflumezopyrim and iodomethane; furthermore, preparations based on Bacillus firmus (I-1582, BioNeem, Votivo), as well as the following known active compounds: 1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazol-5-amine (known from WO2006 / 043635), {1'-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]-5-fluorospiro[indol-3,4'-piperidine]-1(2H)-yl}(2-chloropyridin-4-yl)methanone (known from WO2003 / 106457), 2-chloro-N-[2-{1-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]piperidin-4-yl}-4-(trifluoromethyl)phenyl]isonicotinamide (known from WO2006 / 003494), 3-(2,5-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one (known from WO2009 / 049851), 3-(2,5-Dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-yl-ethylcarbonate (known from WO2009 / 049851), 4-(But-2-yne-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine (known from WO2004 / 099160), 4-(But-2-yne-1-yloxy)-6-(3-chlorophenyl)pyrimidine (known from WO2003 / 076415), PF1364 (CAS Reg. No. 1204776-60-2), Methyl 2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-chloro-3-methylbenzoyl]-2-methylhydrazine carboxylate (known from WO2005 / 085216),Methyl-2-[2-({[3-brom-1-(3-chlorpyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-cyan-3-methylbenzoyl]-2-ethylhydrazincarboxylat (bekannt aus WO2005 / 085216), Methyl-2-[2-({[3-brom-1-(3-chlorpyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-cyan-3-methylbenzoyl1]-2-methylhydrazincarboxylat (bekannt aus WO2005 / 085216), Methyl-2-[3,5-dibrom-2-({[3-brom-1-(3-chlorpyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)benzoyl]-2-ethylhydrazincarboxylat (bekannt aus WO2005 / 085216), N-[2-(5-Amino-1,3,4-thiadiazol-2-yl)-4-chlor-6-methylphenyl]-3-brom-1-(3-chlorpyridin-2-yl)-1H-pyrazol-5-carboxamid (bekannt aus CN102057925), 4-[5-(3,5-Dichlorphenyl)-5-(trifluormethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1-oxidothietan-3-yl)benzamid (bekannt aus WO2009 / 080250), N-[(2E)-1-[(6-Chlorpyridin-3-yl)methyl]pyridin-2(1H)-yliden]-2,2,2-trifluoracetamid (bekannt aus WO2012 / 029672), 1-[(2-Chlor-1,3-thiazol-5-yl)methyl]-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-ium-2-olat (bekannt aus WO2009 / 099929),1-[(6-Chlorpyridin-3-yl)methyl]-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-ium-2-olat (bekannt aus WO2009 / 099929), 4-(3-{2,6-Dichlor-4-[(3,3-dichlorprop-2-en-1-yl)oxy]phenoxy}propoxy)-2-methoxy-6-(trifluormethyl)pyrimidin (bekannt aus CN101337940), N-[2-(tert-Butylcarbamoyl)-4-chlor-6-methylphenyl]-1-(3-chlorpyridin-2-yl)-3-(fluormethoxy)-1H-pyrazol-5-carboxamid (bekannt aus WO2008 / 134969), Butyl-[2-(2,4-dichlorphenyl)-3-oxo-4-oxaspiro[4.5]dec-1-en-1-yl]-carbonat (bekannt aus CN 102060818), 3E)-3-[1-[(6-Chlor-3-pyridyl)methyl]-2-pyridyliden]-1,1,1-trifluor-propan-2-on (bekannt aus WO2013 / 144213), N-(Methylsulfonyl)-6-[2-(pyridin-3-yl)-1,3-thiazol-5-yl]pyridin-2-carboxamid (bekannt aus WO2012 / 000896), N-[3-(Benzylcarbamoyl)-4-chlorphenyl]-1-methyl-3-(pentafluorethyl)-4-(trifluormethyl)-1H-pyrazol-5-carboxamid (bekannt aus WO2010 / 051926), 5-Brom-4-chlor-N-[4-chlor-2-methyl-6-(methylcarbamoyl)phenyl]-2-(3-chlor-2-pyridyl)pyrazole-3-carboxamid (bekannt aus CN103232431), Tioxazafen,4-[5-(3,5-Dichlorphenyl)-4,5-dihydro-5-(trifluormethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxido-3-thietanyl)-benzamid, 4-[5-(3,5-Dichlorphenyl)-4,5-dihydro-5-(trifluormethyl)-3-isoxazolyl]-2-methyl-N-(trans-1-oxido-3-thietanyl)-benzamid und 4-[(5S)-5-(3,5-Dichlorphenyl)-4,5-dihydro-5-(trifluormethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxido-3-thietanyl)benzamid (bekannt aus WO 2013050317 A1), N-[3-Chlor-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluorpropyl)sulfinyl]-propanamid, (+)-N-[3-Chlor-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluorpropyl)sulfinyl]-propanamid und (-)-N-[3-Chlor-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluorpropyl)sulfinyl]-propanamid (bekannt aus WO 2013162715 A2, WO 2013162716 A2, US 20140213448 A1), 5-[[(2E)-3-Chlor-2-propen-1-yl]amino]-1-[2,6-dichlor-4-(trifluoromethyl)phenyl]-4-[(trifluormethyl)sulfinyl]-1H-pyrazol-3-carbonitril (bekannt aus CN 101337937 A),3-Brom-N-[4-chlor-2-methyl-6-[(methylamino)thioxomethyl]phenyl]-1-(3-chlor-2-pyridinyl)-1H-pyrazol-5-carboxamid, (Liudaibenjiaxuanan, bekannt aus CN 103109816 A); N-[4-Chlor-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chlor-2-pyridinyl)-3-(fluormethoxy)-1H-pyrazol-5-carboxamid (bekannt aus WO 2012034403 A1), N-[2-(5-Amino-1,3,4-thiadiazol-2-yl)-4-chlor-6-methylphenyl]-3-brom-1-(3-chlor-2-pyridinyl)-1H-pyrazol-5-carboxamid (bekannt aus WO 2011085575 A1), 4-[3-[2,6-Dichlor-4-[(3,3-dichlor-2-propen-1-yl)oxy]phenoxy]propoxy]-2-methoxy-6-(trifluormethyl)-pyrimidin (bekannt aus CN 101337940 A); (2E)- und 2(Z)-2-[2-(4-Cyanophenyl)-1-[3-(trifluormethyl)phenyl]ethylidene]-N-[4-(difluormethoxy)phenyl]-hydrazine-carboxamid (bekannt aus CN 101715774 A); 3-(2,2-Dichloroethenyl)-2,2-dimethyl-4-(1H-benzimidazol-2-yl)phenyl-cyclopropan-carbonsäureester (bekannt aus CN 103524422 A); (4aS)-7-Chlor-2,5-dihydro-2-[[(methoxycarbonyl)[4-[(trifluormethyl)thio]phenyl]amino]carbonyl]-indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-methyl carboate (known from CN 102391261 A).,
[0084] Beispiele für herbiziden Mischungspartner sind: Acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydimsodium, ametryn, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlorpotassium, aminocyclopyrachlor-methyl, aminopyralid, amitrole, ammoniumsulfamate, anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyron, bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil-butyrate, -potassium, -heptanoate und -octanoate, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chlorbromuron,chlorfenac, chlorfenac-sodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorthal-dimethyl, chlorsulfuron, cinidon, cinidon-ethyl, cinosulfuron, clacyfos, clethodim, clodinafop, clodinafop-propargyl, clomeprop, clopyralid, cloransulam, cloransulammethyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D-butotyl, -butyl, -dimethylammonium, -diolamin, - ethyl, 2-ethylhexyl, -isobutyl, -isooctyl, -isopropylammonium, -potassium, -triisopropanolammonium und -trolamine, 2,4-DB, 2,4-DB-butyl, -dimethylammonium, isooctyl, -potassium und -sodium, daimuron (dymron), dalapon, dazomet, n-decanol, desmedipham, detosyl-pyrazolate (DTP), dicamba, dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl,diclofop-P-methyl, diclosulam, difenzoquat, diflufenzopyr, diflufenzopyr-sodium, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimetrasulfuron, dinitramine, dinoterb, diphenamid, diquat, diquat-dibromid, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, F-9600, F-5231, i.e. N-[2-Chlor-4-fluor-5-[4-(3-fluorpropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]-phenyl]-ethansulfonamid, F-7967, i.e. 3-[7-Chlor-5-fluor-2-(trifluormethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluormethyl)pyrimidin-2,4(1H,3H)-dion, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenpyr, flufenpyr-ethyl,flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, -dimethylammonium und -methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, glufosinate-ammonium, glufosinate-P-sodium, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium, -potassium, -sodium und -trimesium, H-9201, i.e. O-(2,4-Dimethyl-6-nitrophenyl)-O-ethyl-isopropylphosphoramidothioat, halauxifen, halauxifen-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HW-02, i.e. 1-(Dimethoxyphosphoryl)-ethyl-(2,4-dichlorphenoxy)acetat, imazamethabenz, Imazamethabenz-methyl,imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyrisopropylammonium, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxyniloctanoate, -potassium und sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, karbutilate, KUH-043, i.e. 3-({[5-(Difluormethyl)-1-methyl-3-(trifluormethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazol, ketospiradox, lactofen, lenacil, linuron, MCPA, MCPA-butotyl, -dimethylammonium, -2-ethylhexyl, -isopropylammonium, -potassium und - sodium, MCPB, MCPB-methyl, -ethyl und -sodium, mecoprop, mecoprop-sodium, und -butotyl, mecoprop-P, mecoprop-P-butotyl, -dimethylammonium, -2-ethylhexyl und -potassium, mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methiopyrsulfuron,methiozolin, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinat, monolinuron, monosulfuron, monosulfuron-ester, MT-5950, i.e. N-[3-chlor-4-(1-methylethyl)-phenyl]-2-methylpentanamid, NGGC-011, napropamide, NC-310, i.e. 4-(2,4-Dichlorbenzoyl)-1-methyl-5-benzyloxypyrazol, neburon, nicosulfuron, nonanoic acid (Pelargonsäure), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat, paraquat dichloride, pebulate, penoxsulam, pentachlorphenol, pentoxazone, pethoxamid, petroleum oils, phenmedipham, picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron,pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrion, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron, , SYN-523, SYP-249, i.e. 1-Ethoxy-3-methyl-1-oxobut-3-en-2-yl-5-[2-chlor-4-(trifluormethyl)phenoxy]-2-nitrobenzoat, SYP-300, i.e. 1-[7-Fluor-3-oxo-4-(prop-2-in-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidin-4,5-dion, 2,3,6-TBA, TCA (Trifluoressigsäure), TCA-sodium, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton,terbuthylazin, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thiencarbazonemethyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiafenacil, tolpyralate, topramezone, tralkoxydim, triafamone, tri-allate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazin, trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate, vernolate, XDE-848, ZJ-0862, i.e. 3,4-Dichlor-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}anilin, sowie die folgenden Verbindungen: ,
[0085] Examples of plant growth regulators as potential mixing partners are: acibenzolar, acibenzolar-S-methyl, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, brassinolide, catechin, chlormequat chloride, cloprop, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, daminozide, dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal, endothal-dipotassium, -disodium, and mono(N,N-dimethylalkylammonium), ethephon, flumetraline, flurenol, flurenol-butyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid (IAA), 4-indole-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, jasmonic acid methyl ester. maleic hydrazide, mepiquat chloride, 1-methylcyclopropene, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenolate mixture, 4-Oxo-4[(2-phenylethyl)amino]butyric acid, paclobutrazol, N-phenylphthalamic acid, prohexadione, prohexadione-calcium, prohydrojasmone, salicylic acid, strigolactone, tecnazene, thidiazuron, triacontanol,trinexapac, trinexapac-ethyl, cytodef, uniconazole, uniconazole-P.,
[0086] Furthermore, the SCs according to the invention can contain a safener e). The following groups of compounds are suitable as safeners (component e), for example: S1) Compounds from the group of heterocyclic carboxylic acid derivatives: S1 a< ) Compounds of the dichlorophenylpyrazolin-3-carboxylic acid type (S1 a< ), preferably compounds such as 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3-carboxylic acid, 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3-carboxylic acid ethyl ester (S1-1) (“Mefenpyr-diethyl”), and related compounds as described in WO-A-91 / 07874; S1 b< ) Derivatives of dichlorophenylpyrazole carboxylic acid (S1 b< ), preferably compounds such as 1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylic acid ethyl ester (S1-2), 1-(2,4-dichlorophenyl)-5-isopropylpyrazole-3-carboxylic acid ethyl ester (S1-3), 1-(2,4-dichlorophenyl)-5-(1,1-dimethyl-ethyl)pyrazole-3-carboxylic acid ethyl ester (S1-4) and related compounds as described in EP-A-333 131 and EP-A-269 806; S1 c< ) Derivatives of 1,5-diphenylpyrazole-3-carboxylic acid (S1 c< ), preferably compounds such as 1-(2,4-Dichlorophenyl)-5-phenylpyrazole-3-carboxylic acid ethyl ester (S1-5), 1-(2-chlorophenyl)-5-phenylpyrazole-3-carboxylic acid methyl ester (S1-6) and related compounds as described, for example, in EP-A-268554; S1 d< ) compounds of the triazole carboxylic acid type (S1 d< ), preferably compounds such as fenchlorazole(-ethyl ester), i.e. 1-(2,4-dichlorophenyl)-5-trichloromethyl-(1H)-1,2,4-triazole-3-carboxylic acid ethyl ester (S1-7), and related compounds as described in EP-A-174 562 and EP-A-346 620; S1 e< ) Compounds of the type of 5-benzyl or 5-phenyl-2-isoxazoline-3-carboxylic acid, or of 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (S1 e< ), preferably compounds such as 5-(2,4-dichlorobenzyl)-2-isoxazoline-3-carboxylic acid ethyl ester (S1-8) or 5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S1-9) and related compounds as described in WO-A-91 / 08202, or 5,5-diphenyl-2-isoxazoline-carboxylic acid (S1-10) or 5,5-Diphenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S1-11) ("Isoxadifen-ethyl") or -n-propyl ester (S1-12) or 5-(4-Fluorphenyl)-5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S1-13), as described in patent application WO-A-95 / 07897. S2) Compounds from the group of 8-quinoline oxide derivatives (S2): S2 a< ) Compounds of the type of 8-quinoline oxyacetic acid (S2 a< ), preferably (5-chloro-8-quinoline oxy)acetic acid (1-methylhexyl) ester ("cloquintocet-mexyl") (S2-1), (5-chloro-8-quinoline oxy)acetic acid (1,3-dimethyl-but-1-yl) ester (S2-2), (5-chloro-8-quinoline oxy)acetic acid 4-allyl-oxy-butyl ester (S2-3), (5-chloro-8-quinoline oxy)acetic acid 1-allyloxy-prop-2-yl ester (S2-4), (5-chloro-8-quinoline oxy)acetic acid ethyl ester (S2-5), (5-chloro-8-quinoline oxy)acetic acid methyl ester (S2-6), (5-Chloro-8-quinolineoxy)acetic acid allyl ester (S2-7), (5-Chloro-8-quinolineoxy)acetic acid 2-(2-propylidene-iminoxy)-1-ethyl ester (S2-8),(5-Chloro-8-quinolineoxy)acetic acid 2-oxo-prop-1-yl ester (S2-9) and related compounds as described in EP-A-86 750, EP-A-94 349 and EP-A-191 736 or EP-A-0 492 366, as well as (5-chloro-8-quinolineoxy)acetic acid (S2-10), its hydrates and salts, for example its lithium, sodium, potassium, calcium, magnesium, aluminium, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts as described in WO-A-2002 / 34048; S2 b< ) Compounds of the type of (5-chloro-8-quinolineoxy)malonic acid (S2 b< ), preferably compounds such as (5-chloro-8-quinolineoxy)malonic acid diethyl ester, (5-chloro-8-quinolineoxy)malonic acid diallyl ester, (5-chloro-8-quinolineoxy)malonic acid methyl ethyl ester and related compounds as described in EP-A-0 582 198. S3) Active ingredients of the type of dichloroacetamides (S3) commonly used as pre-emergence safeners (soil-active safeners), such as "Dichlormide" (N,N-diallyl-2,2-dichloroacetamide) (S3-1),"R-29148" (3-Dichloracetyl-2,2,5-trimethyl-1,3-oxazolidin) der Firma Stauffer (S3-2), "R-28725" (3-Dichloracetyl-2,2,-dimethyl-1,3-oxazolidin) der Firma Stauffer (S3-3), "Benoxacor" (4-Dichloracetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazin) (S3-4), "PPG-1292" (N-Allyl-N-[(1,3-dioxolan-2-yl)-methyl]-dichloracetamid) der Firma PPG Industries (S3-5), "DKA-24" (N-Allyl-N-[(allylaminocarbonyl)methyl]-dichloracetamid) der Firma Sagro-Chem (S3-6), "AD-67" oder "MON 4660" (3-Dichloracetyl-1-oxa-3-aza-spiro[4,5]decan) der Firma Nitrokemia bzw. Monsanto (S3-7), "TI-35" (1-Dichloracetyl-azepan) der Firma TRI-Chemical RT (S3-8), "Diclonon" (Dicyclonon) oder "BAS145138" oder "LAB145138" (S3-9) ((RS)-1-Dichloracetyl-3,3,8a-trimethylperhydropyrrolo[1,2-a]pyrimidin-6-on) der Firma BASF, "Furilazol" oder "MON 13900" ((RS)-3-Dichloracetyl-5-(2-furyl)-2,2-dimethyloxazolidin) (S3-10),as well as its (R)-isomer (S3-11). S4) Compounds from the class of acylsulfonamides (S4): S4 a< ) N-acylsulfonamides of the formula (S4 a< ) and their salts as described in WO-A-97 / 45016, , wherein RA 1< (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, the latter two substituents being substituted by v A substituents from the group halogen, (C 1 -C 4 )alkoxy, (C 1 -C 6 )haloalkoxy and (C 1 -C 4 )alkylthio and, in the case of cyclic substituents, also by (C 1 -C 4 )alkyl and (C 1 -C 4 )haloalkyl; RA 2< halogen, (C 1 -C 4 )alkyl, (C 1 -C 4 )alkoxy, CF 3 ; m A 1 or 2; v A is 0, 1, 2 or 3; S4 b< ) Compounds of the type of 4-(benzoylsulfamoyl)benzamides of formula (S4 b< ) and their salts, as described in WO-A-99 / 16744, where RB1<, RB2< independently denote hydrogen, (C1-C6)alkyl, (C3-C6)cycloalkyl, (C3-C6)alkenyl, (C3-C6)alkynyl, RB3< halogen, (C1-C4)alkyl, (C1-C4)haloalkyl or (C1-C4)alkoxy and m B1 or 2, e.g., where RB1< = cyclopropyl, RB2< = hydrogen and (RB3<) = 2-OMe (“Cyprosulfamide”, S4-1), RB1< = cyclopropyl, RB2< = hydrogen and (RB3<) = 5-Cl-2-OMe (S4-2), RB1< = ethyl, RB2< = hydrogen and (RB3<) = 2-OMe is (S4-3), RB 1< = isopropyl, RB 2< = hydrogen and (RB 3< ) = 5-Cl-2-OMe is (S4-4) and RB 1< = isopropyl, RB 2< = hydrogen and (RB 3< ) = 2-OMe is (S4-5); S4 c< ) compounds from the class of benzoylsulfamoylphenylureas of the formula (S4 c< ), as described in EP-A-365484, where RC1< , RC2< independently denote hydrogen, (C1-C8)alkyl, (C3-C8)cycloalkyl, (C3-C6)alkenyl, (C3-C6)alkynyl, RC3< halogen, (C1-C4)alkyl, (C1-C4)alkoxy, CF3 and mc1 or 2; for example, 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea, 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea, 1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea; S4 d< ) Compounds of the type of N-phenylsulfonyl terephthalamides of the formula (S4 d< ) and their salts, which are known e.g. from CN 101838227, where RD 4< halogen, (C 1 -C 4 )alkyl, (C 1 -C 4 )alkoxy, CF 3 , m D 1 or 2; RD 5< hydrogen, (C 1 -C 6 )alkyl, (C 3 -C 6 )cycloalkyl, (C 2 -C 6 )alkenyl, (C 2 -C 6 )alkynyl, (C 5 -C 6 )cycloalkenyl. S5) Active substances from the class of hydroxyaromatics and aromatic-aliphatic carboxylic acid derivatives (S5), e.g. 3,4,5-triacetoxybenzoic acid ethyl ester, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicyclic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO-A-2004 / 084631, WO-A-2005 / 015994, WO-A-2005 / 016001. S6) Active substances from the class of 1,2-dihydroquinoxalin-2-ones (S6), e.g. 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one, 1-methyl-3-(2-thienyl)-1,2-dihydro-quinoxalin-2-thione, 1-(2-aminoethyl)-3-(2-thienyl)-1,2-dihydro-quinoxalin-2-one hydrochloride, 1-(2-methylsulfonylaminoethyl)-3-(2-thienyl)-1,2-dihydro-quinoxalin-2-one, as described in WO-A-2005 / 112630.S7) Compounds of the class of diphenylmethoxyacetic acid derivatives (S7), e.g., methyl diphenylmethoxyacetic acid ester (CAS Reg. No. 41858-19-9) (S7-1), ethyl diphenylmethoxyacetic acid ester, or diphenylmethoxyacetic acid as described in WO-A-98 / 38856. S8) Compounds of formula (S8) as described in WO-A-98 / 27049, wherein the symbols and indices have the following meanings: . RD 1< is halogen, (C 1 -C 4 )alkyl, (C 1 -C 4 )haloalkyl, (C 1 -C 4 )alkoxy, (C 1 -C 4 )haloalkoxy, RD 2< is hydrogen or (C 1 -C 4 )alkyl, RD 3< is hydrogen, (C 1 -C 8 )alkyl, (C 2 -C 4 )alkenyl, (C 2 -C 4 )alkynyl, or aryl, wherein each of the aforementioned C-containing residues is unsubstituted or substituted by one or more, preferably up to three identical or different, residues from the group consisting of halogen and alkoxy; or their salts, n D is an integer from 0 to 2. S9) Active substances from the class of 3-(5-tetrazolylcarbonyl)-2-quinolones (S9), e.g. 1,2-Dihydro-4-hydroxy-1-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS Reg. No.: 219479-18-2), 1,2-Dihydro-4-hydroxy-1-methyl-3-(5-tetrazolyl-carbonyl)-2-quinolone (CAS Reg. No. 95855-00-8), as described in WO-A-1999 / 000020. S10) Compounds of the formulas (S10 a< ) or (S10 b< ) as described in WO-A-2007 / 023719 and WO-A-2007 / 023764, wherein RE 1< halogen, (C 1 - C 4 )alkyl, methoxy, nitro, cyano, CF 3 , OCF 3 YE , ZE independently of each other O or S, n E an integer from 0 to 4, RE 2< (C 1 - C 16 )alkyl, (C 2 - C 6 )alkenyl, (C 3 - C 6 )cycloalkyl, aryl; benzyl, halogenbenzyl, RE 3< hydrogen or (C 1 - C 6 )alkyl. S11) Active substances of the type of oxyimino compounds (S11) known as seed dressings, such as e.g. B. "Oxabetrinil" ((Z)-1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (S11-1), known as a seed treatment safener for millet against metolachlor damage, "Fluxofenim" (1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethanone-O-(1,3-dioxolan-2-ylmethyl)-oxime) (S11-2), known as a seed treatment safener for millet against metolachlor damage, and "Cyometrinil" or "CGA-43089" ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (S11-3), known as a seed treatment safener for millet against metolachlor damage. S12) Active substances from the class of isothiochromanones (S12), such asMethyl-[(3-oxo-1H-2-benzothiopyran-4(3H)-ylidene)methoxy]acetate (CAS Reg. No. 205121-04-6) (S12-1) and related compounds from WO-A-1998 / 13361. S13) One or more compounds from group (S13): "Naphthalic anhydride" (1,8-naphthalenedicarboxylic anhydride) (S13-1), known as a seed treatment safener for maize against damage from thiocarbama herbicides, "Fenclorim" (4,6-dichloro-2-phenylpyrimidine) (S13-2), known as a safener for pretilachlor in seeded rice, "Flurazole" (benzyl-2-chloro-4-trifluoromethyl-1,3-thiazol-5-carboxylate) (S13-3), known as a seed treatment safener for millet against damage from alachlor and metolachlor, "CL 304415" (CAS Reg. No. 31541-57-8) (4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4) of the company American Cyanamide, known as a safener for maize against damage from imidazolinones, "MG 191" (CAS Reg. No. 96420-72-3) (2-Dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) of Nitrokemia, known as a safener for maize, "MG 838" (CAS Reg.No. 133993-74-5) (2-propenyl 1-oxa-4-azaspiro[4.5]decane-4-carbodithioate) (S13-6) of the company Nitrokemia "Disulfoton" (O,O-Diethyl S-2-ethylthioethyl phosphordithioate) (S13-7), "Dietholate" (O,O-Diethyl-O-phenylphosphorothioate) (S13-8), "Mephenate" (4-Chlorophenyl-methylcarbamate) (S13-9). S14) Active ingredients which, in addition to a herbicidal effect against weeds, also have a safener effect on cultivated plants such as rice, such as e.g."Dimepiperate" or "MY-93" (S-1-methyl-1-phenylethyl-piperidine-1-carbothioate), known as a rice safener against damage from the herbicide Molinate; "Daimuron" or "SK 23" (1-(1-methyl-1-phenylethyl)-3-p-tolyl-urea), known as a rice safener against damage from the herbicide Imazosulfuron; "Cumyluron" = "JC-940" (3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenylethyl)urea, see JP-A-60087254), known as a rice safener against damage from some herbicides; "Methoxyphenone" or "NK 049" (3,3'-dimethyl-4-methoxybenzophenone), known as a rice safener against damage from some herbicides; "CSB" (1-Bromo-4-(chloromethylsulfonyl)benzene) from Kumiai, (CAS Reg. No. 54091-06-4), which is known as a safener against damage caused by some herbicides in rice. S15) Compounds of formula (S15) or their tautomers, as described in WO-A-2008 / 131861 and WO-A-2008 / 131860, . wherein RH1< denotes a (C1-C6)haloalkyl group and RH2< denotes hydrogen or halogen and RH3< , RH4< independently denote hydrogen, (C1-C16)alkyl, (C2-C16)alkenyl or (C2-C16)alkynyl, each of the latter 3 groups being unsubstituted or by one or more groups from the group consisting of halogen, hydroxy, cyano, (C1-C4)alkoxy, (C1-C4)haloalkoxy, (C1-C4)alkylthio, (C1-C4)alkylamino, di[(C1-C4)alkyl]amino, [(C1-C4)alkoxy]carbonyl, [(C1-C4)haloalkoxy]carbonyl, (C3-C 6) Cycloalkyl, which is unsubstituted or substituted, phenyl, which is unsubstituted or substituted, and heterocyclyl, which is unsubstituted or substituted, or (C3-C6) cycloalkyl, (C4-C6) cycloalkenyl, (C3-C6) cycloalkyl fused to one side of the ring with a 4- to 6-membered saturated or unsaturated carbocyclic ring, or (C4-C6) cycloalkenyl,which is condensed on one side of the ring with a 4- to 6-membered saturated or unsaturated carbocyclic ring, wherein each of the latter 4 residues is unsubstituted or by one or more residues from the group consisting of halogen, hydroxy, cyano, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy, (C1-C4)alkylthio, (C1-C4)alkylamino, di[(C1-C4)alkyl]amino, [(C1-C4)alkoxy]carbonyl, [(C1-C4)haloalkoxy]carbonyl, (C3-C6)cycloalkyl, which is unsubstituted or substituted, phenyl, which unsubstituted or substituted, and heterocyclyl, which is unsubstituted or substituted, is substituted, or RH 3< means (C 1 -C 4 )-alkoxy, (C 2 -C 4 )alkenyloxy, (C 2 -C 6 )alkynyloxy or (C 2 -C 4 )haloalkoxy, and RH 4< means hydrogen or (C 1 -C 4 )-alkyl, or RH 3< and RH 4< together with the directly bonded N atom form a four- to eight-membered heterocyclic ring,which, in addition to the N atom, may also contain further heteroring atoms, preferably up to two further heteroring atoms from the group N, O and S, and which is unsubstituted or substituted by one or more residues from the group halogen, cyano, nitro, (C1-C4)alkyl, (C1-C4)haloalkyl, (C1-C4)alkoxy, (C1-C4)haloalkoxy and (C1-C4)alkylthio. S16) Active substances that are primarily used as herbicides, but also have a safener effect on cultivated plants, e.g. B. (2,4-Dichlorophenoxy)acetic acid (2,4-D), (4-Chlorphenoxy)acetic acid, (R,S)-2-(4-chloro-o-tolyloxy)propionic acid (Mecoprop), 4-(2,4-Dichlorophenoxy)butyric acid (2,4-DB), (4-Chloro-o-tolyloxy)acetic acid (MCPA), 4-(4-Chloro-o-tolyloxy)butyric acid, 4-(4-Chlorphenoxy)butyric acid, 3,6-Dichloro-2-methoxybenzoic acid (Dicamba), 1-(Ethoxycarbonyl)ethyl-3,6-dichloro-2-methoxybenzoate (Lactidichloro-ethyl). ,
[0087] Preferred safeners according to the present invention are safeners based on the esters of cloquintocet (preferably mexyl esters) and / or mefenpyr (preferably as diethyl esters), particularly preferably mefenpyr diethyl esters.
[0088] Organic thickeners are preferably suitable as thickeners (f), and these can be natural, biotechnologically modified, or organically synthetic thickeners.
[0089] Typical synthetic thickeners are Rheostrux® (Croda), Thixin®, or Thixatrol® series (Elementis). These are typically acrylate-based. Typical organic thickeners are based on xanthan gum or cellulose (such as hydroxyethyl or carboxymethylcellulose) or a combination thereof. Naturally modified xanthan gum-based thickeners are preferred. Typical examples are Rhodopol® (Solvay), Kelzan® (CPKelco Corp.), and Satiaxane® (Cargill). Other thickeners include carrier materials (f) that are preferably selected from the group containing minerals, carbonates, sulfates, and phosphates of alkaline earth and earth metals, such as calcium carbonate; polymeric carbohydrates; silicas; and (natural) framework silicates, such as kaolin.Typical examples of suitable fillers c) are, for example, Agsorb ®< LVM-GA (attapulgite), Harborlite ®< 300 (perlite), Collys ®< HV (modified starch), Omya ®< -chalk (calcium carbonate), Kaolin ®< Tec 1 (kaolin, aluminum hydrosilicate), Steamic ®< OOS (talc, magnesium silicate).
[0090] Further preferred for f) are natural framework silicates and calcium carbonate types such as Omya®< -chalk (calcium carbonate), Kaolin®< Tec 1 (kaolin) and Harborlite®< 300 (perlite), particularly preferred are natural framework silicates such as Kaolin®< Tec 1 (kaolin, aluminum hydrosilicate) and Harborlite®< 300 (perlite). Further fillers in the SC formulations according to the invention are selected from the group containing minerals, carbonates, sulfates and phosphates of alkaline earth and earth metals, such as calcium carbonate, polymeric carbohydrates, framework silicates such as low-absorption precipitated silicas and natural framework silicates such as kaolin. Typical examples of suitable fillers c) are, for example, Agsorb ®< LVM-GA (attapulgite), Harborlite ®< 300 (perlite), Collys ®< HV (modified starch), Omya ®< -chalk (calcium carbonate), Kaolin ®< Tec 1 (kaolin, aluminum hydrosilicate), Steamic ®< OOS (talc, magnesium silicate).Suitable examples include modified natural silicates, such as chemically modified bentonites, hectorites, attapulgites, montmorillonites, smectites or other silicate minerals, such as Bentone ®< (Elementis), Attagel ®< (Engelhard), Agsorb ®< (Oil-Dri Corporation) or Hectorite ®< (Akzo Nobel) or the Van Gel ®< series (RT Vanderbilt).
[0091] Particularly preferred are carrier materials f) selected from the group of highly absorbent carriers with an absorption capacity of at least 200 g of dibutyl phthalate per 100 g of carrier material (BET surface according to ISO 9277), such as synthetic precipitated silica of high absorbency (Sipernat® types) and pyrogenic silica (Aerosil® types).
[0092] Other additives and auxiliary substances g) are wetting agents, pH adjusters, defoamers, biocides, disintegrants, adhesion promoters, antifreeze, preservatives, dyes or fertilizers, as well as various surfactants from component b), preferably antifreeze, defoamers and biocides.
[0093] Suitable defoamers are surface-active compounds based on silicone or silane, such as the Tegopren® products (Goldschmidt), the SE® products (Wacker), as well as the Bevaloid® (Kemira), Rhodorsil® (Solvay) and Silcolapse® products (Blustar Silicones). SE® (Wacker), Rhodorsil® and Silcolapse® products are preferred; products such as Silcolapse® 5020 are particularly preferred.
[0094] Suitable antifreeze agents are those from the group of ureas, diols and polyols, such as ethylene glycol and propylene glycol, glycerin preferably propylene glycol or glycerin.
[0095] Suitable biocides include products such as Acticide ®< MBS (Biocide, Thor Chemie), CIT, MIT or BIT, such as Proxel ®< GXL (BIT), Acticide ®< SPX (MIT, CIT).
[0096] Suitable adhesion promoters can be selected from the group consisting of polyvinylpyrrolidone (PVP), polyvinyl alcohol, PVP-dimethylaminoethyl methacrylate copolymer, butylated PVP, vinyl chloride-vinyl acetate copolymer, sodium salt of the propensultanoic acid-partially hydrolyzed vinyl acetate copolymer, sodium caseinate, phenolic resins, and modified cellulose types such as Luviskol® (polyvinylpyrrolidone) and Mowiol® (polyvinyl alcohol).
[0097] Polyvinylpyrrolidone types are preferred, especially low molecular weight types such as Luviskol ®< K30.
[0098] Suitable disintegrants can be selected from the group of modified carbohydrates, such as microcrystalline cellulose and cross-linked polyvinylpyrrolidones, for example Avicel® < PH 101 (microcrystalline cellulose), Agrimer® < XLF (cross-linked polyvinylpyrrolidone), Disintex® < 200 (cross-linked polyvinylpyrrolidone). Cross-linked polyvinylpyrrolidones, such as Agrimer® < XLF, are preferred.
[0099] Suitable antifoaming agents can be selected from the group of phosphoric acid esters with lower alcohols, C6-C10 alcohols, silicone surfactants (suspoemulsions of hydrophobized silica particles in aqueous emulsion concentrates based on liquid silicone surfactants), such as polydimethylsiloxane, and their absorbates onto solid carrier material, such as Rhodorsil® < 432 (silicone surfactant), butyl phosphate, isobutyl phosphate, n-octanol, Wacker ASP15 (polydimethylsiloxane, absorbed onto a solid carrier), and antifoam agent SE (polydimethylsiloxane). Suspoemulsions of hydrophobized silica particles in aqueous emulsion concentrates based on liquid silicone surfactants, such as antifoam agent SE (polydimethylsiloxane), and solid antifoam agents, such as Wacker ASP 15 (polydimethylsiloxane), are preferred.
[0100] The invention further relates to a herbicidal agent which can be produced from the SCs according to the invention by dilution with liquids, preferably water.
[0101] It can be advantageous to add further active ingredients, preferably agrochemical active ingredients (e.g., as tank mix partners in the form of appropriate formulations) and / or excipients and additives commonly used in application, e.g., self-emulsifying oils such as vegetable oils or paraffin oils and / or fertilizers, to the herbicidal agents thus obtained. The present invention therefore also relates to such agents, preferably herbicides, based on the formulations according to the invention.
[0102] A particular embodiment of the invention relates to the use of the herbicidal agents obtainable from the SCs according to the invention for controlling unwanted plant growth, hereinafter referred to as "herbicidal agent".
[0103] These herbicidal products exhibit excellent efficacy against a broad spectrum of economically important monocotyledonous and dicotyledonous weeds. Even difficult-to-control perennial weeds that sprout from rhizomes, rootstocks, or other dormant organs are effectively controlled. The herbicidal products can be applied, for example, by pre-sowing, pre-emergence, or post-emergence methods. The following are some examples of monocotyledonous and dicotyledonous weeds that can be controlled by these herbicidal products, without implying a limitation to specific species.
[0104] On the monocotyledonous weed side, for example Apera spica venti, Avena spp., Alopecurus spp., Brachiaria spp., Digitaria spp., Lolium spp., Echinochloa spp., Panicum spp., Phalaris spp., Poa spp., Setaria spp., as well as Bromus spp. such as Bromus catharticus, Bromus secalinus, Bromus erectus, Bromus tectorum and Bromus japonicus, and Cyperus species from the annual group, and on the perennial species side Agropyron, Cynodon, Imperata, as well as Sorghum and also perennial Cyperus species are well covered. In dicotyledonous weed species, the spectrum of activity extends to species such as Abutilon spp., Amaranthus spp., Chenopodium spp., Chrysanthemum spp., Galium spp. (including Galium aparine, Ipomoea spp.), Kochia spp., Lamium spp., Matricaria spp., Pharbitis spp., Polygonum spp., Sida spp., Sinapis spp., Solanum spp., Stellaria spp., Veronica spp. and Viola spp., Xanthium spp., on the annual side, as well as Convolvulus, Cirsium, Rumex and Artemisia among the perennial weeds.
[0105] The formulations according to the invention are preferably used in rice, maize, wheat, barley, oats, rye, millet and rapeseed.
[0106] Under the specific growing conditions of rice, weeds such as Echinochloa, Sagittaria, Alisma, Eleocharis, Scirpus, and Cyperus are also effectively controlled by herbicides. If the herbicides are applied to the soil surface before germination, either the emergence of the weed seedlings is completely prevented, or the weeds grow to the cotyledon stage, then cease growth and finally die completely after three to four weeks.
[0107] The aforementioned properties and advantages are beneficial in practical weed control, helping to keep agricultural crops free of unwanted competing plants and thus securing and / or increasing yields in terms of both quality and quantity. These new herbicidal products significantly exceed current technical standards with regard to the described properties.
[0108] Although these herbicidal products exhibit excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, cultivated plants of economically important crops, e.g., dicotyledonous crops such as soybeans, cotton, rapeseed, sugar beets, or grass crops such as wheat, barley, rye, oats, millet, rice, or maize, are only minimally affected or not at all. For these reasons, the herbicidal products available are very well suited for the selective control of unwanted plant growth in agricultural crops or ornamental plantings.
[0109] Furthermore, depending on the crop, the corresponding herbicidal agents exhibit excellent growth-regulating properties. They regulate the plant's own metabolism and can therefore be used to selectively influence plant constituents and facilitate harvesting, for example, by inducing desiccation and stunted growth. They are also potentially suitable for the general control and inhibition of unwanted vegetative growth without killing the plants. Inhibition of vegetative growth plays a significant role in many monocot and dicot crops, as it can reduce or completely prevent storage.
[0110] Due to their herbicidal and plant growth-regulating properties, herbicidal agents—as already mentioned—can also be used to control weeds in crops of known or yet-to-be-developed genetically modified plants. Transgenic plants are generally characterized by particularly advantageous properties, such as resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens such as certain insects or microorganisms like fungi, bacteria, or viruses. Other special properties relate, for example, to the harvested crop in terms of quantity, quality, storability, composition, and specific constituents. For instance, transgenic plants with increased starch content or altered starch quality, or those with a different fatty acid composition of the harvested crop, are known.
[0111] The application of these herbicidal agents is preferred in economically important transgenic crops of crops and ornamental plants, e.g., grass crops such as wheat, barley, rye, oats, millet, rice, and maize, or crops of sugar beet, cotton, soybeans, rapeseed, potatoes, tomatoes, peas, and other vegetables. The herbicidal agents can preferably be used in crops that are resistant to the phytotoxic effects of the herbicides or have been genetically engineered to be resistant.
[0112] When applying herbicidal agents in transgenic crops, in addition to the effects observed in other crops against weeds, effects often occur that are specific to the application in the respective transgenic crop, for example, an altered or specifically expanded weed spectrum that can be controlled, altered application rates that can be used, preferably good combinationability with the other herbicidal active ingredients to which the transgenic crop is resistant, as well as influencing the growth and yield of the transgenic crop plants.
[0113] The present invention therefore relates to a method for controlling unwanted plant growth, preferably in crops such as cereals (e.g., wheat, barley, rye, oats, rice, maize, millet), sugar beet, sugar cane, rapeseed, cotton, and soybeans, particularly preferably in monocotyledonous crops such as cereals, e.g., wheat, barley, rye, oats, and hybrids thereof such as triticale, rice, maize, and millet, characterized in that the herbicidal agents according to the invention are applied to the weed plants, plant parts, plant seeds, or the area on which the plants grow, e.g., the cultivated area. The crops may also be genetically modified or obtained through mutation selection and are preferably tolerant to acetolactate synthase (ALS) inhibitors.
[0114] With the formulations according to the invention, a better biological effect can be achieved with the same application rate. Advantageously and surprisingly, the formulations according to the invention exhibit excellent plant compatibility and a reduced tendency to cause phytotoxic damage.
[0115] In addition, the formulations according to the invention, as special active ingredient combination formulations (synonymous: mixture formulations, co-formulations), have further advantages, such as lower packaging costs than when using individual active ingredients, which simplifies the effort for production, transport and storage, and makes the preparation of the spray solutions used in agriculture easier to handle due to the smaller quantities and the already established, effective ratios, e.g., during the measuring and mixing process.
[0116] The formulations according to the invention additionally exhibit surprisingly excellent dispersing and stabilizing properties after further dilution with liquids, preferably water.
[0117] In addition, the formulations result in long-term storage-stable and technically flawless formulations.
[0118] Furthermore, the formulations according to the invention exhibit particularly good herbicidal properties in dry soils, especially when DCPMI and flufenacet are used.
[0119] The particle size is determined according to CIPAC (CIPAC = Collaborative International Pesticides Analytical Council; www.cipac.org) method MT 187 as d50 or d90 (active ingredient particle size laser scattering 50% or 90% of all volume particles). The mean particle size is the d50 value.
[0120] The invention is explained in more detail by the following examples. Examples Substances used and abbreviations:
[0121] The terms used in the following examples have the following meanings: Flufenacet 4'-Fluoro-N-isopropyl-2-(5-trifluoromethyl-1,3,4-thiadiazol-2-yloxy)acetanilide (Bayer AG), hereinafter abbreviated FFA, log P = 3.2; DCPMI 2-[(2,4-Dichlorophenyl)-methyl]-4,4'-dimethyl-3-isoxazolidinone (CAS number 81777-95-9 or IUPAC 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, hereinafter abbreviated DCPMI), log P = 3.39; Morwet® < D-425; Naphthalenesulfonic acid formaldehyde condensate sodium salt (Nouryon); Pluronic® < PE 10500; Propylene oxide-ethylene oxide (PO-EO) block polymer (BASF); Citric acid polybasic organic acid Rhodopol® < GXanthan Derivative (Solvay) Aerosil® < 200 Synthetic amorphous silica (silicon dioxide, Evonik) Silcolapse® < 426R, 411 Silicone defoamer (Elkam) Glycerin Antifreeze Proxel® < GXL Preservative (Biocide, Proxel) Adjuvant 1C8-C10 Alkyl polyglycoside, D-glucopyranose oligomer - decyl octyl glycosides, 60% glycoside and 40% water, CAS number 68515-73-1, BASF, Agnique® < PG 8105, log P 1.77 Adjuvant 2 Polyoxyethylene sorbitan fatty acid ester (20 EO), sorbitan monooleate, ethoxylated, composed of oleic acid, with sorbitol and its anhydrides, CAS number 9005-65-6, Croda, Tween ® < 80, log P ca. 2; Adjuvant 3 Polyoxyethylene sorbitan fatty acid ester (20 EO), sorbitan monolaurate, ethoxylated, composed of lauric acid, with sorbitol and its anhydrides, CAS number 9005-64-5, Croda, Tween ® < 20, log P ca. -0.55; .
[0122] The log P describes the distribution of pesticide active ingredients between water and n-octanol.
[0123] Banerjee et al., 1980, S. Banerjee, SH Yalkowsky, SC Valvani, Water solubility and octanol / water partition coefficients of organics. Limitations of the solubility-partition coefficient correlation, Environ. Sci. Technol., 14 (1980), pp. 1227-1229. Production example SC formulations:
[0124] For the production of the ZC formulations according to the invention, the following SC formulations were prepared as mixing partners. These are mixed with the formulations according to the invention to form further formulations according to the invention. Preparation of an aqueous suspension concentrate:
[0125] To produce the examples listed in Table 1, water at room temperature is first added. The remaining components are then added while stirring (in no particular order). This is followed by wet milling, for example using a bead mill. Finally, the organic thickener is added. Table 1: Manufactured formulations (Values are given in percent by weight, wt.%) SC-1 SC-2 A DCPMI 42,37 A Flufenacet 42,37 B Morwet ®< D-425 1,0 1,0 B Pluronic® < PE 10500 5 5 G Citric acid 0,1 0,1 F Aerosil® < 200 0,5 0,5 F Rhodopol ®< 23 0,2 0,2 G Silcolapse ®< 411 0,5 0,5 G Glycerin 5 5 G Proxel® < GXL 0,18 0,18 Water is added to bring the total volume to 100%. Density of the formulation 1,19 1,19 g / L content of active ingredient 500 500 Manufactured finished formulations
[0126] The finished formulations were prepared by mixing SC-1 and SC-2 by adding the corresponding amounts of adjuvant. Weight percentages were used in each case. For comparison, the respective formulations were taken as 100%. The finished formulations were tested in the greenhouse. Greenhouse experiments:
[0127] In the standard experimental procedure, seeds of different weed and grass biotypes (provenances) were sown in a pot 8-13 cm in diameter filled with natural soil from a standard field soil (loamy silt; non-sterile) and covered with a layer of soil approximately 1 cm thick. The pots were then cultivated in a greenhouse (12-16 hours of light, daytime temperature 20-22°C, nighttime temperature 15-18°C) until the time of application. The pots were treated on a laboratory sprayer with spray solutions containing the mixtures / compositions according to the invention, mixtures from the prior art, or the individual components. The active ingredients or combinations of active ingredients, formulated as WG, WP, EC, or otherwise, were applied at the corresponding growth stages of the plants. The water volume for the spray application was 100-600 l / ha. After treatment, the plants were returned to the greenhouses.
[0128] Approximately 3 weeks after application, the soil and / or foliar effect was visually assessed on a scale of 0-100% in comparison to an untreated control group: 0% = no discernible effect compared to the untreated control group; 100% = complete effect compared to the untreated control group.
[0129] (Notes: The term "seed" also includes vegetative propagation forms, such as rhizome pieces; abbreviations used: h light = hours of illumination, g AS / ha = grams of active substance per hectare, l / ha = liters per hectare, S = sensitive, R = resistant) 1. Pre-emergence weed control: Seeds of various weed and grass biotypes (provenances) were sown in a pot 8-13 cm in diameter filled with natural soil from a standard field (loamy silt; non-sterile) and covered with a layer of soil approximately 1 cm thick. The pots were then cultivated in a greenhouse (12-16 hours of light, daytime temperature 20-22°C, nighttime temperature 15-18°C) until application. At seed / plant growth stages BBCH 00-10, the pots were treated on a laboratory sprayer with spray solutions containing the inventive mixtures / compositions, mixtures, or the individual components applied as WG, WP, EC, or other formulations. The water volume for spray application was 100-600 l / ha. After treatment, the plants were returned to the greenhouses and fertilized and irrigated as needed. 2.Post-emergence weed control: Seeds of various weed and grass biotypes (provenances) were sown in a pot 8-13 cm in diameter filled with natural soil from a standard field (loamy silt; non-sterile) and covered with a layer of soil approximately 1 cm thick. The pots were then cultivated in a greenhouse (12-16 hours of light, daytime temperature 20-22°C, nighttime temperature 15-18°C) until application. At different BBCH growth stages between seeds / plants 11-25, i.e., generally between two and three weeks after the start of cultivation, the pots were treated on a laboratory sprayer with spray solutions containing the inventive mixtures / compositions, mixtures, or the individual components applied as WG, WP, EC, or other formulations. The water volume for spray application was 100-600 l / ha.After treatment, the plants were returned to the greenhouses and fertilized and watered as needed. 3. Pre-emergence weed control with and without incorporation of active ingredient: Seeds of different weed and grass biotypes (provenances) were sown in a pot 8-13 cm in diameter filled with natural soil from a standard field (loamy silt; non-sterile). The pots containing the seeds were then compared either at BBCH stage 00-10 of the seeds / plants, i.e.,Generally, between two and three weeks after the start of cultivation, the plants were treated on a laboratory sprayer with spray solutions containing the inventive mixtures / compositions, mixtures, or the individually applied components as WG, WP, EC, or other formulations, or an equivalent amount of the inventive mixtures / compositions, mixtures, or the individually applied components as WG, WP, EC, or other formulations was incorporated into the 1 cm top layer. The water volume for the spray application was 100-600 l / ha. After treatment, the plants were placed back in the greenhouses and fertilized and irrigated as needed. The pots were cultivated in a greenhouse (12-16 hours of light, daytime temperature 20-22°C, nighttime temperature 15-18°C). 4.Selectivity effect in pre-emergence: Seeds of different crop types (provenances) were sown in a pot 8-13 cm in diameter filled with natural soil from a standard field soil (loamy silt; non-sterile) and covered with a layer of soil approximately 1 cm thick. The pots were then cultivated in a greenhouse (12-16 hours of light, daytime temperature 20-22°C, nighttime temperature 15-18°C) until the time of application. At BBCH growth stages 00-10, the pots were treated on a laboratory sprayer with spray solutions containing the inventive mixtures / compositions, mixtures, or the individual components applied as WG, WP, EC, or other formulations. The water volume for the spray application was 100-600 l / ha. After treatment, the plants were returned to the greenhouses and fertilized and irrigated as needed. 5.Post-emergence selectivity: Seeds of different crop types (origins) were sown in a pot 8-13 cm in diameter filled with natural soil from a standard field soil (loamy silt; non-sterile) and covered with a layer of soil approximately 1 cm thick. The pots were then cultivated in a greenhouse (12-16 hours of light, daytime temperature 20-22°C, nighttime temperature 15-18°C) until application. At different BBCH growth stages 11-32 of the seeds / plants, i.e., generally between two and four weeks after the start of cultivation, the pots were treated on a laboratory sprayer with spray solutions containing the inventive mixtures / compositions, mixtures, or the individually applied components as WG, WP, EC, or other formulations. The water volume for the spray application was 100-600 l / ha. After treatment, the plants were placed back in the greenhouses and fertilized and watered as needed.The pots were cultivated in a greenhouse (12-16 hours of light, daytime temperature 20-22°C, nighttime temperature 15-18°C). 6. Weed control in pre-sowing applications: Seeds of different weed and grass biotypes (provenances) were sown in a pot 8-13 cm in diameter filled with natural soil from a standard field (loamy silt; non-sterile). Before sowing, the pots containing the seeds were treated on a laboratory sprayer with spray solutions containing the inventive mixtures / compositions, mixtures, or the individually applied components as WG, WP, EC, or other formulations. The water volume for the spray application was 100-600 l / ha. After sowing, the pots were placed in the greenhouses and fertilized and irrigated as needed. The pots were cultivated in a greenhouse (12-16 hours of light, daytime temperature 20-22°C, nighttime temperature 15-18°C). 7.Pre- and post-emergence weed control under different cultivation conditions: Seeds of various weed and grass biotypes (provenances) were sown in a pot 8-13 cm in diameter filled with natural soil from a standard field (loamy silt; non-sterile) and covered with a layer of soil approximately 1 cm thick. The pots were then cultivated in a greenhouse (12-16 hours of light, daytime temperature 20-22°C, nighttime temperature 15-18°C) until application. At different BBCH growth stages 00-25, the pots were treated on a laboratory sprayer with spray solutions containing the inventive mixtures / compositions, mixtures, or the individual components applied as WG, WP, EC, or other formulations. The water volume for spray application was 100-600 l / ha. After treatment, the plants were returned to the greenhouses and fertilized and irrigated as needed.The pots were cultivated in a greenhouse (12-16 hours of light, daytime temperature 20-22°C, nighttime temperature 15-18°C). Irrigation was varied according to the research question. The individual comparison groups were watered in stages, ranging from above the PWP (permanent wilt point) to the level of the maximum field capacity. 8. Pre- and post-emergence weed control under different irrigation conditions: Seeds of different weed and grass biotypes (provenances) were sown in a pot 8-13 cm in diameter filled with natural soil from a standard field soil (loamy silt; non-sterile) and covered with a layer of soil approximately 1 cm thick. The pots were then cultivated in a greenhouse (12-16 hours of light, daytime temperature 20-22°C, nighttime temperature 15-18°C) until the time of application.The pots were treated at different BBCH growth stages 00-25 of the seeds / plants on a laboratory sprayer with spray solutions containing the mixtures / compositions according to the invention, mixtures, or with the individually applied components as WG, WP, EC, or other formulations. The water volume for the spray application was 100-600 l / ha. After treatment, the plants were returned to the greenhouses and fertilized and irrigated as needed. The pots were cultivated in a greenhouse (12-16 hours of light, daytime temperature 20-22°C, nighttime temperature 15-18°C). The individual comparison groups were exposed to different irrigation techniques. Irrigation was carried out either from below or in stages from above (simulated sprinkler irrigation).Pre- and post-emergence weed control under different soil conditions: Seeds of various weed and grass biotypes (origins) were sown in a pot 8-13 cm in diameter filled with natural soil and covered with a soil layer of approximately 1 cm. To compare herbicidal activity, the plants were cultivated in different potting soils, ranging from sandy to heavy clay, and with varying organic matter contents. The pots were then cultivated in a greenhouse (12-16 hours of light, daytime temperature 20-22°C, nighttime temperature 15-18°C) until application. At different BBCH growth stages 00-25, the pots were treated on a laboratory sprayer with spray solutions containing the inventive mixtures / compositions, mixtures, or the individual components applied as WG, WP, EC, or other formulations.The water volume for the spray application was 100-600 l / ha. After treatment, the plants were returned to the greenhouses and fertilized and irrigated as needed. The pots were cultivated in a greenhouse (12-16 hours of light, daytime temperature 20-22°C, nighttime temperature 15-18°C). 10. Pre- and post-emergence weed control for resistant grass / weed species: Seeds of different weed and grass biotypes (provenances) with varying resistance mechanisms to different modes of action were sown in an 8 cm diameter pot filled with natural soil from a standard field soil (loamy silt, LSI; pH 7.4; % C org 2.2) and covered with a soil layer of approximately 1 cm. The pots were then cultivated in a greenhouse (12-16 hours of light, daytime temperature approx. 23°C, nighttime temperature approx. 15°C) until the time of application.The pots were treated at different BBCH growth stages 00-25 of the seeds / plants on a laboratory sprayer with spray solutions containing the mixtures / compositions according to the invention, mixtures, or with the individually applied components as WG, WP, EC, or other formulations. The water volume for the spray application was 300 l / ha. After treatment, the plants were returned to the greenhouses and fertilized and irrigated as needed. The pots were cultivated in a greenhouse (12-16 hours of light, daytime temperature approx. 23°C, nighttime temperature approx. 15°C). 11. Weed control and crop selectivity in pre- and post-emergence under different sowing conditions: Seeds of different weed and grass biotypes (provenances) and crop species (provenances) were sown in a pot with a diameter of 8-13 cm filled with natural soil and covered with a soil layer of approximately 0-5 cm.The pots were then cultivated in a greenhouse (12-16 hours of light, daytime temperature 20-22°C, nighttime temperature 15-18°C) until the time of application. At different BBCH growth stages 00-25 of the seeds / plants, the pots were treated on a laboratory sprayer with spray solutions containing the inventive mixtures / compositions, mixtures, or the individually applied components as WG, WP, EC, or other formulations. The water volume for the spray application was 100-600 l / ha. After treatment, the plants were returned to the greenhouses and fertilized and irrigated as needed. The pots were cultivated in a greenhouse (12-16 hours of light, daytime temperature 20-22°C, nighttime temperature 15-18°C). 12.Pre- and post-emergence weed control at different soil pH levels: Seeds of various weed and grass biotypes (provenances) were sown in a pot 8-13 cm in diameter filled with natural soil and covered with a layer of soil approximately 1 cm thick. To compare herbicidal activity, the plants were cultivated in seed-starting mixes, standard field soil (loamy silt; non-sterile) with different pH values of 7.4 and 8.4. The soil was adjusted with lime to achieve the higher pH. The pots were then cultivated in a greenhouse (12-16 hours of light, daytime temperature 20-22°C, nighttime temperature 15-18°C) until application.The pots were treated at different BBCH growth stages 00-10 of the seeds / plants on a laboratory sprayer with spray solutions containing the mixtures / compositions according to the invention, mixtures, or with the individually applied components as WG, WP, EC, or other formulations. The water volume for the spray application was 100-600 l / ha. After treatment, the plants were returned to the greenhouses and fertilized and irrigated as needed. The pots were cultivated in a greenhouse (12-16 hours of light, daytime temperature 20-22°C, nighttime temperature 15-18°C).
[0130] The investigations were carried out at different soil moisture levels.
[0131] Humid conditions: The test pots were watered daily with 1 liter of water per m².
[0132] Dry conditions: The test pots were watered daily with 0.25 liters of water per m².
[0133] Normal conditions: The test pots were watered daily with 0.5 liters of water per m². Results from the greenhouse:
[0134] The formulations were tested for their efficacy against typical weeds and grasses using comparison examples 1-3. The application window was early pre-emergence (BBCH 11). The greenhouse application rate was 100 g / ha DCPMI, which correlates with a typical field application rate of 200 g / ha DCPMI (the transfer factor from greenhouse to field is therefore 2). The pots were tested under moist, normal, and dry conditions. Flufenacet was tested at 125 g / ha. The formulation was mixed with the adjuvant and then applied. A dilution of 100 L / ha of water was typically used. Application rate used in g / ha
[0135] Example Wording used FFA g / ha DCPMI g / ha Adjuvant 1 g / ha Adjuvant 2 g / ha Comparison 1 SC-1 100 Comparison 2 SC-2 125 Example 1 SC-1 with Adjuvant 1 100 1000 Example 2 SC-1 with Adjuvant 1 100 500 Example 3 SC-1 with Adjuvant 1 100 250 Example 4 SC-1 with Adjuvant 2 100 1000 Example 5 SC-1 with Adjuvant 2 100 500 Example 6 SC-1 with Adjuvant 2 100 250 Example 7 SC-2 with Adjuvant 1 125 1000 Example 8 SC-2 with Adjuvant 1 125 500 Example 9 SC-2 with Adjuvant 1 125 250 Example 10 SC-2 with Adjuvant 2 125 1000 Example 11 SC-2 with Adjuvant 2 125 500 Example 12 SC-2 with Adjuvant 2 125 250
[0136] Efficacy against grass weeds under moist, dry, and normal conditions. The following important grass weeds in winter cereals were investigated in each case: AVEFA = Avena fatua = Wild oats ALOMY = Alopecurus myosuroides = Blackgrass APESY = Apera spica-venti = Common Windgrass LOLMU = Lolium multiflorum = Italian ryegrass
[0137] Wording used % Control against AVEFA / ALOMY / APESY / LOLMU % Control against AVEFA / ALOMY / APESY / LOLMU % Control against AVEFA / ALOMY / APESY / LOLMU dry normal moist Comparison 1 40 / 95 / 10 / 95 30 / 95 / 10 / 80 30 / 90 / 10 / 80 Comparison 2 30 / 90 / 100 / 30 80 / 100 / 100 / 85 95 / 98 / 100 / 95 Example 1 40 / 100 / 10 / 95 30 / 95 / 20 / 90 40 / 100 / 10 / 95 Example 2 40 / 100 / 10 / 95 30 / 95 / 20 / 80 40 / 90 / 10 / 80 Example 3 70 / 95 / 10 / 95 50 / 100 / 10 / 90 30 / 100 / 10 / 90 Example 4 80 / 95 / 10 / 95 30 / 90 / 20 / 90 40 / 99 / 10 / 90 Example 5 70 / 99 / 10 / 95 50 / 95 / 10 / 95 40 / 90 / 10 / 90 Example 6 60 / 99 / 10 / 99 30 / 90 / 10 / 70 35 / 100 / 10 / 90 Example 7 40 / 95 / 100 / 90 80 / 98 / 100 / 98 95 / 100 / 100 / 98 Example 8 40 / 95 / 100 / 70 90 / 98 / 100 / 97 95 / 100 / 100 / 97 Example 9 40 / 95 / 100 / 60 80 / 98 / 100 / 95 95 / 98 / 100 / 97 Example 10 40 / 95 / 100 / 30 50 / 100 / 100 / 70 90 / 100 / 100 / 98 Example 11 40 / 95 / 100 / 30 45 / 100 / 100 / 70 90 / 100 / 100 / 100 Example 12 40 / 98 / 100 / 30 40 / 100 / 100 / 70 85 / 100 / 100 / 95
[0138] The two selected active ingredients, especially with adjuvants, show significant improvements against AVEFA and LOLMU. For better comparability, the absolute improvement in percentage points is shown in the following table. The figures are taken from the table above and show the percentage reduction / control of the weeds AVEFA and LOLMU under the respective conditions. AVEFA LOLMU AVEFA LOLMU AVEFA LOLMU dry dry normal normal Moist moist Comparison 2 30 30 80 85 95 95 Example 9 40 60 80 95 95 97 improvement 10 30 0 10 0 2 Example 8 40 70 90 97 95 97 improvement 10 40 10 12 0 2 Example 7 40 90 80 98 95 98 improvement 10 60 0 13 0 3 Example 12 40 30 40 70 85 95 improvement 10 0 -40 -15 -10 0 Example 11 40 30 45 70 90 100 improvement 10 0 -35 -15 -5 5 Example 10 40 30 50 70 90 98 improvement 10 0 -30 -15 -5 3 AVEFA LOLMU AVEFA LOLMU AVEFA LOLMU dry dry normal normal moist moist Comparison 1 40 95 30 80 30 80 Example 3 70 95 50 90 30 90 improvement 30 0 20 10 0 10 Example 2 40 95 30 80 40 80 improvement 0 0 0 0 10 0 Example 1 40 95 30 90 40 95 improvement 0 0 0 10 10 15 Example 6 60 99 30 70 35 90 improvement 20 4 0 -10 5 10 Example 5 70 95 50 95 40 90 improvement 30 0 20 15 10 10 Example 4 80 95 30 90 40 90 improvement 40 0 0 10 10 10
[0139] The formulations according to the invention with the herbicidal active ingredients show a significantly higher efficacy with the two adjuvants 1 and 2. The adjuvants show a particularly marked improvement in efficacy under dry conditions. With flufenacet, it was found that adjuvant 1, in particular, showed a consistent and marked improvement in efficacy between 250 and 1000 g / ha. Adjuvant 2 showed better efficacy under dry conditions and poorer efficacy under moist conditions.
[0140] DCPMI showed a significant improvement with both adjuvants even at doses as low as 250 g / ha.
[0141] However, the mixtures of SC-1 and -2 with Adjuvant 3 showed no improvement in efficacy.
Claims
1. Formulation comprising a) DCPMI and / or Flufenacet, b) at least one dispersant, c) a synergist, characterized in that c) is an alkylpolysaccharide, and that the proportion of synergist c) in the formulation is 5.0 to 95.0% by weight, d) optionally at least one agrochemical active ingredient different from a), e) optionally at least one safener, f) optionally at least one thickener, g) optionally further additional and auxiliary substances, and h) water.
2. Formulation according to claim 1, characterized in that the proportion of active ingredient a) in the formulations according to the invention is 0.5 to 55.0% by weight, more preferred 0.5 to 45.0% by weight, even more preferred 5.0 to 40.0% by weight, and particularly preferred 10.0 to 40.0% by weight.
3. Formulation according to claim 1 or 2, characterized in that the proportion of dispersant b) is 1.0 to 15.0% by weight, more preferred 2.0 to 10.0% by weight and most preferred 2.5 to 8.0% by weight.
4. Formulation according to one or more of the preceding claims, characterized in that the proportion of synergist c) in the formulation is 10.0 to 90.0% by weight and most preferred 20.0 to 80.0% by weight.
5. Formulation according to one or more of the preceding claims, characterized in that a combination of at least one ionic and one non-ionic dispersant is used as the dispersant, preferably a combination of sulfonates, and a non-ionic dispersant from the group of tristyrylphenol ethoxylates, tristyrylphenol ethoxy-propoxylates and castor oil polyglycol ether esters.
6. Formulation according to one of the preceding claims, characterized in that the alkylpolysaccharide has a general structure of formula (I): R5-O-(sug)u (I), wherein R5 is an unbranched or branched, optionally substituted or unsubstituted, hydrocarbyl moiety selected from the group consisting of alkyl, alkenyl, alkylphenyl and alkenylphenyl, preferably with 4 to 22 carbon atoms, and the sug unit is a saccharide moiety with an open or cyclic structure wherein the saccharide moiety is selected from the group comprising monosaccharides, disaccharides and polysaccharides.
7. Use of the formulation according to claim 1 as a herbicide on dry soils.
8. Use of the formulation according to claim 1 as a herbicide in rice, corn, wheat, barley, oats, rye, millet, and canola in pre-emergence.
9. Use according to claim 8 on dry soils.
10. Use according to one of claims 7 - 9 against Avena fatua (wild oat), Alopecurus myosuroides (blackgrass), Apera spica-venti (loose silky-bent) and Lolium multiflorum (Italian ryegrass).