AU2018352050A1 - Aqueous (2-(2,4-dichlorophenyl)methyl)-4,4-dimethyl-3-isoxazolidinone-based suspension concentrates - Google Patents

Abstract

The present invention relates to aqueous 2-[(2,4-dichlorophenyl)methyl]-4,4'-dimethyl-3-isoxazolidinone-based suspension concentrates, the production thereof and to the mixtures thereof with suspension concentrates and the use thereof as agrochemical formulations with low volatility and damage to adjacent cultures.

Description

Aqueous 12-(2,4-dichlorophenyl)methyll-4,4-dimethyl-3-isoxazolidinone-based suspension concentrates

The present invention relates to aqueous suspension concentrates based on 2-[(2,4-dichlorophenyl)methyl] 4,4'-dimethyl-3-isoxazolidinone, their preparation and their mixtures with suspension concentrates and their use as agrochemical formulation with reduced volatility and less damage to neighbouring crops ("non-target plants").

The active compound 2-[(2,4-dichlorophenyl)methyl]-4,4'-dimethyl-3-isoxazolidinone (CAS number 81777-95-9 or IPUAC 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, abbreviated hereinafter to DCPMI), is a chemical derivative of clomazone (abbreviated hereinafter to CPMI, CAS 81777-89-1, IUPAC 2-(2-chlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one). By comparison with clomazone, DCPMI has much lower water solubility (39.5 ppm rather than 1000 ppm) and a somewhat lower vapour pressure (0.88 mPa rather than 19.2 niPa), and so the calculated Henry volatility constant (distribution of the active compound through the water gas phase) is at a similar level. Both active compounds belong to the class of the volatile active compounds that can cause unwanted damage to neighbouring crops. The high vapour pressure may also be associated with an unwanted broad distribution, which should be prevented for reasons of human and environmental toxicology and for economic reasons.

DCPMI is used in herbicidal compositions and mixtures or employed as a selective grass herbicide, as described, for example, in WO-A 2015/127259 or WO-A 2012/148689.

Capsule suspensions (CS) and suspension concentrates (SC) of DCPMI are known from PCT/EP 2017/0690701 and WO 2015/127259. A disadvantage of the suspension concentrates known from this prior art is their volatility and the resulting damage to neighbouring and crop plants.

Another disadvantage of CS formulations is that the active compound has to be encapsulated. An encapsulation process is technically more complex and more expensive than the production of a suspension concentrate. A further disadvantage is that the encapsulation leads to a slow and often late release of the active compound, which can impair the action, so that weeds can recover or resistances can develop. So that the herbicide can still develop its effect, it must be used in higher concentrations, which in turn is ecologically and economically undesirable.

DCPMI is preferably combined with further non-encapsulated herbicidally active compounds which are also present as a suspension concentrate. With this type of application, a quick effect is desired, since in the event of too late an onset of action the weeds and grasses may already have progressed too far in growth, so that successful control is no longer possible.

The object of the present invention was therefore to provide a suspension concentrate of DCPMI which significantly reduces the volatility of the active compound, preferably by at least 20% (relative). In addition, a better effect than with a comparable capsule suspension is to be achieved, damage to neighbouring crops and crop plants being reduced or, ideally, being avoided entirely in comparison with the formulations known from the prior art.

The object was achieved with the suspension concentrates (SC) according to the invention. Accordingly, the present invention provides an aqueous suspension concentrate comprising a) 2-[(2,4-dichlorophenyl)methyl-4,4'-dimethyl]-3-isoxazolidinone, b) at least one dispersant, c) carrier material, d) optionally at least one agrochemical active compound different from a), e) optionally at least one safener, f) optionally at least one thickener, and g) optionally further additives and auxiliaries.

The SC according to the invention preferably contains components d and e), more preferably components d), e and f), as further essential constituents.

In a further embodiment, the SC according to the invention contains components a) to d) as essential constituents, more preferably components a)-f) and particularly preferably components a) to g).

The dispersant b) is preferably a mixture of an ionic dispersant b2) and a non-ionic dispersant b1).

The agrochemical active compounds d) different from a) can be selected from the group of herbicides, insecticides, fungicides and nematocides; preferably d) is another herbicide, with preference selected from the group comprising auxins, pigment synthesis inhibitors, DOXP synthase inhibitors and VLCFA inhibitors. The present invention furthermore provides a process in which component a) 2-[(2,4 dichlorophenyl)methyl-4,4'-dimethyl]-3-isoxazolidinone is added with stirring to an aqueous solution containing a dispersant b and a carrier material c). More preferably, the aqueous solution contains an ionic and a non-ionic dispersant. Components d) to g) can furthermore be added in the combinations described above.

The present invention likewise provides water-dispersible suspension concentrates (SCs) obtainable by the process according to the invention.

The SC according to the invention can be produced by those methods known in the prior art, for example by wet grinding of the components in bead mills (such as discontinuous bead mills or continuous bead mills), or colloid mills (such as toothed colloid mills).

The proportion of water in the formulations according to the invention may generally be 25 to 98% by weight, preferably 35 to 85% by weight, with water supplementing the proportion of components a) - g) to 100% by weight.

Here and in the entire description, unless defmed otherwise, the unit "% by weight" (per cent by weight) relates to the relative weight of the respective component based on the total weight of the formulation of the concentrate.

The formulation may typically contain residues of organic solvents from the additives of from 0 to 5.0% by weight, preferably from 0.1 to 2.5% by weight. The proportion of DCPMI (component a) in the formulations according to the invention is 0.5% to 35% by weight, preferably 5% to 30% by weight, particularly preferably 10% to 30% by weight and most preferably 15% to 25% by weight.

If further active compounds d) are present in the SC, the total proportion of components a) and d) is 0.5 to 35.0% by weight, preferably 5 to 30% by weight, particularly preferably 10.0 to 30.0% by weight and very particularly preferably 15.0 to 25.0% by weight, i.e. the proportion of component a) is reduced by component d).

The proportion of dispersant (component b) is preferably 1.0 to 15.0% by weight, more preferably 2.0 to 10.0% by weight and very particularly preferably 2.5 to 8.0% by weight.

A mixture of bl) and b2 is preferably used, the proportion of the anionic dispersant bl) in the suspension concentrates according to the invention being 0.1 to 10% by weight, preferably 0.2 to 7.0% by weight and very particularly preferably 0.3 to 4.0% by weight, and the proportion of the non-ionic dispersant b2) in the suspension concentrates according to the invention being 1.0 to 15.0% by weight, preferably 2.0 to 10.0% by weight and very particularly preferably 2.5 to 8.0% by weight, where the total proportion as defmed above is not exceeded by the sum of bl) and b2).

In a particularly preferred embodiment, the proportion of bl) is 0.3 to 1.5% by weight and the proportion of b2) is 2.5 to 7.5% by weight. The proportion of carrier material (component c) in the SCs according to the invention is preferably 0.1 to 10.0% by weight, more preferably 0.3 to 8.0% by weight and very particularly preferably 1.0 to 7.0% by weight.

The ratio of a) to c) is preferably from 1 to 10, more preferably from 2 to 8, particularly preferably 3-6 and most preferably 4.

The proportion of agrochemical active compounds different from a) (component d) is as defamed above.

The proportion of safener (component e) is preferably 1.0 to 15.0% by weight, more preferably 2.0-12.0% by weight, and particularly preferably 3.0 to 8.0% by weight.

The proportion of thickeners f) in the SCs according to the invention is preferably 0% to 2.0% by weight, with preference 0.01% to 1.00% by weight, particularly preferably 0.01% to 0.60% by weight, very particularly preferably 0.04% to 0.50% by weight and very particularly preferably 0.05% to 0.3% by weight.

The proportion of further auxiliaries and additives g) optionally added in the dispersions according to the invention is preferably 0 to 20.0% by weight, with preference 1.0 to 15.0% by weight, more preferably 3.0 to 10.0% by weight and particularly preferably 5.0 to 10.0% by weight. In respect of the abovementioned proportions of the respective ingredients, it will be clear to the person skilled in the art that the preferred ranges for the individual ingredients can be combined freely with one another, and so these compositions of different preferred ranges for individual ingredients are also considered to be disclosed.

However, particular preference is given, unless stated otherwise, to preferred ranges from the same level, i.e. for example all preferred or more preferred ranges, where a specific disclosure is not intended to replace these general combinations but to add to them. A combination of the most preferred (smallest) preferred ranges is particularly preferred.

The same applies to other specifications of preferred ranges elsewhere in the present description.

In a preferred embodiment, the proportion of component a) is 0.5 to 35% by weight b) is 1.0 to 15% by weight, c) is 0.1 to 10% by weight d) is 0% e) is 1-15%by weight, f) is 0.01 to 1.00% by weight, and g) is 0 to 20% by weight, with water being added to 100% by weight.

In a more preferred embodiment, the proportion of component a) is 0.5 to 35% by weight b) is 1.0 to 15% by weight, c) is 0.1 to 10% by weight d) optionally at least one agrochemical active compound different from a), e) is 1.0 to 15.0% by weight, f) is 0.01 to 1.00% by weight, and g) is I to 15% by weight, with water being added to 100% by weight. In a further preferred embodiment, the proportion of component a) is 5 to 30% by weight, b) is 2.0 to 10% by weight, c) is 0.3 to 8.0% by weight d) optionally at least one agrochemical active compound different from a), e) is 2.0 to 12.0% by weight, f) is 0.01 to 0.60% by weight, and g) is 3.0 to 10.0% by weight, with water being added to 100% by weight.

In a further preferred embodiment, the proportion of component a) is 10 to 30% by weight b) is 2.50 to 8.0% by weight, c) is 1.0 to 7.0% by weight d) optionally at least one agrochemical active compound different from a), e) is 3.0 to 8.0% by weight, f) is 0.04 to 0.50% by weight, and g) is 5.0 to 10.0% by weight, with water being added to 100% by weight.

In a particularly preferred embodiment, the proportion of component a) is 15 to 25% by weight b) is 2.5.0 to 8.0% by weight, c) is 1.0 to 7.0% by weight d) optionally at least one agrochemical active compound different from a), e) is 3.0 to 8.0% by weight, f) is 0.05 to 0.30% by weight, and g) is 5.0 to 10.0% by weight, with water being added to 100% by weight.

If in the embodiments mentioned above further active compounds d) are present in the SC, the total proportion of components a) and d) is 0.5 to 35% by weight, preferably 5 to 30% by weight, particularly preferably 10 to 30% by weight and very particularly preferably 15.0 to 25.0% by weight, i.e. the proportion of component a) is reduced by component d).

In the embodiments described above, b) is preferably furthermore a mixture of b1) and b2, the proportion of the anionic dispersant b) in the suspension concentrates according to the invention being 0.1 to 10% by weight, preferably 0.2 to 7% by weight and very particularly preferably 0.3 to 4.0% by weight, and the proportion of the non-ionic dispersant b2) in the suspension concentrates according to the invention being 1.0 to 15.0% by weight, preferably 2.0 to 10.0% by weight and very particularly preferably 2.5 to 8.0% by weight, where the total proportion as defined above is not exceeded by the sum of bl) and b2).

In a particularly preferred embodiment, the proportion of bl) is 0.3 to 1.5% by weight and the proportion of b2) is 2.5 to 7.5% by weight.

Suitable anionic dispersants bl), such as emulsifiers, surfactants, wetting agents and dispersers, are, for example, alkali metal, alkaline earth metal or ammonium salts of sulfonates, sulfates, phosphates, carboxylates and mixtures thereof, for example the salts of alkylsulfonic acids or alkylphosphoric acids and alkylarylsulfonic or alkylarylphosphoric acids, diphenylsulfonates, alpha-olefinsulfonates, 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 are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates and carboxylated alcohol ethoxylates or alkylphenol ethoxylates. Likewise suitable is the group of anionic emulsifiers of the alkali metal, alkaline earth metal and ammonium salts of the polystyrenesulfonic acids, salts of the polyvinylsulfonic acids, salts of the alkylnaphthalenesulfonic acids, salts of alkylnaphthalenesulfonic acid-formaldehyde condensation products, salts of condensation products of naphthalenesulfonic acid, phenolsulfonic acid and formaldehyde. Examples are calcium dodecylbenzenesulfonate such as Rhodocal@ 70/B (Solvay), Phenylsulfonat CA100 (Clariant) or isopropylammonium dodecylbenzenesulfonates such as Atlox@ 3300B (Croda).

Further typical representatives include Phenylsulfonat CA (calcium dodecylbenzenesulfonate), Soprophor@ products (optionally esterified derivatives of tristyrylphenol ethoxylates), Emulsogen@ 3510 (alkylated EO/PO copolymer), Emulsogen@ EL 400 (ethoxylated castor oil), Tween@ products (fatty acylated sorbitan ethoxylates), Calsogen®AR 100 (calcium dodecylbenzenesulfonate). Preference is given to combinations of salts of alkylated aromatic sulfonic acids, such as Phenylsulfonat CA and/or Calsogen® AR 100, with alkylated copolymers of ethylene oxide and propylene oxide, such as Emulsogen® 3510. Particular preference is given to combinations of salts of dodecylbenzenesulfonic acid, such as Calsogen®AR 100, with alkylated copolymer of ethylene oxide and propylene oxide, such as Emulsogen® 3510.

Examples of further anionic emulsifiers b1) from the group of naphthalenesulfonates are Galoryl® MT 800 (sodium dibutylnaphthalenesulfonic acid), Morwet® IP (sodium diisopropylnaphthalenesulfonate) and Nekal® BX (alkylnaphthalenesulfonate). Examples of anionic surfactants from the group of the condensates of naphthalenesulfonates with formaldehyde are Galoryl@ DT 201 (naphthalenesulfonic acid hydroxy polymer with formaldehyde and methylphenol sodium salt), Galoryl@ DT 250 (condensate of phenol- and naphthalenesulfonates), Reserve C (condensate of phenol- and naphthalenesulfonates) or Morwet@ D 425, Tersperse@ 2020. Preference is given to 1,2-dibutyl- or -diisobutyl-substituted naphthalenesulfonates, for example products such as Galoryl@ MT 800 (CFPI-Nufarm) and Nekal® BX (BASF). Further typical surfactants are Soprophor®3D33, Soprophor®4D384, Soprophor® BSU, Soprophor® CY/8 (Solvay) and Hoe@ S3474 and in the form of Sapogenat T products (Clariant), for example Sapogenat® T 100. Further typical representatives are based on lignin (such as ligninsulfonates, Borresperse@NA, REAX®88 or Kraftsperse 25 S).

From the above-mentioned anionic dispersing aids bl), preference is given to using various sulfonates, particularly preferably those based on naphthalene. Useful nonionic dispersants b2), such as emulsifiers, wetting agents, surfactants and dispersers, include standard surface-active substances present in formulations of agrochemical active compounds. Examples include ethoxylated nonylphenols, reaction products of linear or branched alcohols with ethylene oxide and/or propylene oxide, ethylene oxide-propylene oxide block copolymers, end group-capped and non-end group-capped alkoxylated linear and branched, saturated and unsaturated alcohols (e.g. butoxy polyethylenepropylene glycols), reaction products of alkylphenols with ethylene oxide and/or propylene oxide, ethylene oxide-propylene oxide block copolymers, polyethylene glycols and polypropylene glycols, and also fatty acid esters, fatty acid polyglycol ether esters, alkylsulfonates, alkylsulfates, arylsulfates, ethoxylated arylalkylphenols, for example tristyrylphenol ethoxylate having an average of 16 ethylene oxide units per molecule, and also ethoxylated and propoxylated arylalkylphenols, and also sulfated or phosphated arylalkylphenol ethoxylates or ethoxy- and propoxylates. Particular preference is given to tristyrylphenol alkoxylates and fatty acid polyglycol ether esters. Very particular preference is given to tristyrylphenol ethoxylates, tristyrylphenol ethoxy propoxylates and castor oil polyglycol ether esters, in each case individually or in mixtures. Additives may additionally be useful, such as surfactants or esters of fatty acids, which contribute to improvement in biological efficacy. Suitable nonionic emulsifiers b2) are, for example, Soprophor®796/P, Lucramul CO30, Lucramul® HOT, Lucramul® PSI 100 or Synperonic T304.

Suitable nonionic dispersers b2) may likewise be selected from the group comprising polyvinylpyrrolidone (PVP), polyvinyl alcohol, copolymer of PVP and dimethylaminoethyl methacrylate, butylated PVP, copolymer of vinyl chloride and vinyl acetate, and partially hydrolysed vinyl acetate, phenol resins, modified cellulose types, for example Luviskol® (polyvinylpyrrolidone), Mowiol® (polyvinyl alcohol) or modified cellulose. Preference is given to polyvinylpyrrolidone types, particular preference to types of low molecular weight such as Luviskol®K30 or Sokalan® K30.

Further preferred nonionic emulsifiers b2) from the group of the di- and triblock copolymers of alkylene oxides are, for example, compounds based on ethylene oxide and propylene oxide, having mean molar masses between 200 and 10 000 and preferably 1000 to 4000 g/mol, where the proportion by mass of the polyethoxylated block varies between 10 and 80%, for example the Synperonic@ PE series (Uniqema), the Pluronic®PE series (BASF), the VOP® 32 or Genapol PF series (Clariant).

The carrier materials c) are preferably selected from the group comprising minerals, carbonates, sulfates and phosphates of alkaline earth metals and earth metals, such as calcium carbonate, polymeric carbohydrates, silicas, (natural) framework silicates, such as kaolin. Typical representatives of suitable fillers c) are, for example, Agsorb®LVM®-GA (attapulgite), Harborlite®300 (pearlite), Collys® HV (modified starch), Omya@ chalk (calcium carbonate), Kaolin® Tee 1 (kaolin, aluminium hydrosilicate), Steamic® OOS (talc, magnesium silicate).

For c), preference is furthermore given here to natural framework silicates and calcium carbonate products such as Omya@ chalk (calcium carbonate), Kaolin Tee 1@ (kaolin) and Harborlite® 300 (pearlite), particular preference to natural framework silicates such as Kaolin®, Tec@1 (kaolin, aluminum hydrosilicate) and Harborlite®300 (pearlite). Further fillers in the SC formulations according to the invention are selected from the group comprising minerals, carbonates, sulfates and phosphates of alkaline earth metals and earth metals, such as calcium carbonate, polymeric carbohydrates, framework silicates, such as precipitated silicas having low absorption, and natural framework silicates, such as kaolin. Typical representatives of suitable fillers c) are, for example, Agsorb® LVM®-GA (attapulgite), Harborlite® 300 (pearlite), Collys® HV (modified starch), Omya@ chalk (calcium carbonate), Kaolin® Tee 1 (kaolin, aluminium hydrosilicate), Steamic@ OOS (talc, magnesium silicate). Suitable are, for example, 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 (R.T. Vanderbilt).

Particular preference is given to carrier materials c) selected from the group of the high absorbency carriers having an absorbency of at least 200 g of dibutyl phthalate per 100 g of carrier material (BET surface according to ISO 9277), for example high absorbency synthetic fumed silica (Sipernat@ types) and pyrogenic silica (Aerosil@ types).

Agrochemical active compounds different from component a) (component d) are herbicides, fungicides, insecticides, plant growth regulators and the like.

Fungicidally active compounds are, for example, 1) ergosterol biosynthesis inhibitors, for example (1.001) cyproconazole, (1.002) difenoconazole, (1.003) epoxiconazole, (1.004) fenhexamid, (1.005) fenpropidin, (1.006) fenpropimorph, (1.007) fenpyrazamine, (1.008) fluquinconazole, (1.009) flutriafol, (1.010) imazalil, (1.011) imazalil sulfate, (1.012) ipconazole, (1.013) metconazole, (1.014) myclobutanil, (1.015) paclobutrazole, (1.016) prochloraz, (1.017) propiconazole, (1.018) prothioconazole, (1.019) pyrisoxazole,

(1.020) spiroxamine, (1.021) tebuconazole, (1.022) tetraconazole, (1.023) triadimenol, (1.024) tridemorph, (1.025) triticonazole, (1.026) (1R,2S,5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4 triazol-1-ylmethyl)cyclopentanol, (1.027) (1S,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1 (IH-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.028) (2R)-2-(1-chlorocyclopropyl)-4-[(lR)-2,2 dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol (1.029) (2R)-2-(1-chlorocyclopropyl)-4-[(1S) 2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.030) (2R)-2-[4-(4-chlorophenoxy)-2 (trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.031) (2S)-2-(1-chlorocyclopropyl)-4

[(1R)-2,2-dichlorocyclopropyl]-1-(H-1,2,4-triazol-1-yl)butan-2-ol, (1.032) (2S)-2-(1-chlorocyclopropyl) 4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.033) (2S)-2-[4-(4 chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.034) (R)-[3-(4-chloro 2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.035) (S)-[3-(4-chloro-2 fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.036) [3-(4-chloro-2 fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.037) 1-({(2R,4S)-2-[2 chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole, (1.038) 1 ({(2S,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole, (1.039) 1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-y thiocyanate, (1.040) 1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H 1,2,4-triazol-5-yl thiocyanate, (1.041) 1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2 yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (1.042) 2-[(2R,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy 2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.043) 2-[(2R,4R,5S)-1-(2,4 dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (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-triazole 3-thione, (1.045) 2-[(2R,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4 dihydro-3H-1,2,4-triazole-3-thione, (1.046) 2-[(2S,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6 trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.047) 2-[(2S,4R,5S)-1-(2,4 dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.048) 2

[(2S,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole 3-thione, (1.049) 2-[(2S,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4 dihydro-3H-1,2,4-triazole-3-thione, (1.050) 2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4 yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.051) 2-[2-chloro-4-(2,4-dichlorophenoxy)phenyl]-1-(H 1,2,4-triazol-1-yl)propan-2-ol, (1.052) 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1 yl)butan-2-ol, (1.053)2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2 ol, (1.054) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)pentan-2-ol, (1.055) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1 H-1,2,4-triazol-1-yl)propan-2-ol, (1.056) 2 {[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.057) 2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H 1,2,4-triazole-3-thione, (1.058) 2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2 yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.059) 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-

1-(IH-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.060) 5-(allylsulfanyl)-1-{[3-(2-chlorophenyl)-2-(2,4 difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.061) 5-(allylsulfanyl)-1-{[rel(2R,3R)-3-(2 chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.062) 5-(allylsulfanyl)-1 {[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.063) N' (2,5-dimethyl-4-{[3-(1,1,2,2-tetrafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N methylimidoformamide, (1.064) N'-(2,5-dimethyl-4-{[3-(2,2,2-trifluoroethoxy)phenyl]sulfanyl}phenyl)-N ethyl-N-methylimidoformamide, (1.065) N'-(2,5-dimethyl-4-{[3-(2,2,3,3 tetrafluoropropoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (1.066) N'-(2,5-dimethyl 4-{[3-(pentafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (1.067) N'-(2,5 dimethyl-4-{3-[(1,1,2,2-tetrafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (1.068) N'-(2,5-dimethyl-4-{3-[(2,2,2-trifluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N methylimidoformamide, (1.069) N'-(2,5-dimethyl-4-{3-[(2,2,3,3 tetrafluoropropyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (1.070) N'-(2,5-dimethyl 4-{3-[(pentafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (1.071) N'-(2,5 dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoformamide, (1.072) N'-(4-{[3 (difluoromethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide, (1.073) N'-(4 {3-[(difluoromethyl)sulfanyl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide, (1.074) N'-[5-bromo-6-(2,3-dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimidoformamide, (1.075) N'-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N methylimidoformamide, (1.076) N'-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3 yl}-N-ethyl-N-methylimidoformamide, (1.077) N'-{5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2 methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.078) N'-{5-bromo-6-[(cis-4 isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.079) N'-{5-bromo 6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.080) N'-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.081) mefentrifluconazole, (1.082) ipfentrifluconazole.

2) Inhibitors of the respiratory chain in complex I orII, 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-epimeric enantiomer IR,4S,9S), (2.011) isopyrazam (anti-epimeric enantiomer IS,4R,9R), (2.012) isopyrazam (anti-epimeric racemate IRS,4SR,9SR), (2.013) isopyrazam (mixture of the syn-epimeric racemate 1RS,4SR,9RS and the anti epimeric racemate IRS,4SR,9SR), (2.014) isopyrazam (syn-epimeric enantiomer IR,4S,9R), (2.015) isopyrazam (syn-epimeric enantiomer IS,4R,9S), (2.016) isopyrazam (syn-epimeric racemate IRS,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-pyrazole-4 carboxamide, (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-pyrazole-4- carboxamide, (2.025) 1-methyl-3-(trifluoromethyl)-N-[2'-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4 carboxamide, (2.026) 2-fluoro-6-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4 yl)benzamide, (2.027) 3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-iH pyrazole-4-carboxamide, (2.028) 3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-iH inden-4-yl]-1H-pyrazole-4-carboxamide, (2.029) 3-(difluoromethyl)-1-methyl-N-[(3S)-1,1,3-trimethyl-2,3 dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.030) 3-(difluoromethyl)-N-(7-fluoro-1,1,3 trimethyl-2,3-dihydro-1H-inden-4-yl)-1-methyl-iH-pyrazole-4-carboxamide, (2.031) 3-(difluoromethyl) N-[(3R)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-iH-pyrazole-4-carboxamide, (2.032) 3-(difluoromethyl)-N-[(3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-iH pyrazole-4-carboxamide, (2.033) 5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2 yl]oxy}phenyl)ethyl]quinazolin-4-amine, (2.034) N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3 (difluoromethyl)-5-fluoro-1-methyl-iH-pyrazole-4-carboxamide, (2.035) N-(2-tert-butyl-5-methylbenzyl) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-iH-pyrazole-4-carboxamide, (2.036) N-(2-tert butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-iH-pyrazole-4-carboxamide, (2.037) N (5-chloro-2-ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-iH-pyrazole-4 carboxamide, (2.038) N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1 methyl-iH-pyrazole-4-carboxamide, (2.039) N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4 methanonaphthalen-5-yl]-3-(difluoromethyl)-i-methyl-iH-pyrazole-4-carboxamide, (2.040) N-[(1S,4R)-9 (dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-i-methyl-iH pyrazole-4-carboxamide, (2.041) N-[1-(2,4-dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-1 methyl-iH-pyrazole-4-carboxamide, (2.042) N-[2-chloro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3 (difluoromethyl)-5-fluoro-1-methyl-iH-pyrazole-4-carboxamide, (2.043) N-[3-chloro-2-fluoro-6 (trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-i-methyl-iH-pyrazole-4 carboxamide, (2.044) N-[5-chloro-2-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro 1-methyl-iH-pyrazole-4-carboxamide, (2.045) N-cyclopropyl-3-(difluoromethyl)-5-fluoro--methyl-N-[5 methyl-2-(trifluoromethyl)benzyl]-1H-pyrazole-4-carboxamide, (2.046) N-cyclopropyl-3-(difluoromethyl) 5-fluoro-N-(2-fluoro-6-isopropylbenzyl)--methyl-iH-pyrazole-4-carboxamide, (2.047) N-cyclopropyl-3 (difluoromethyl)-5-fluoro-N-(2-isopropyl-5-methylbenzyl)--methyl-iH-pyrazole-4-carboxamide, (2.048) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-i-methyl-iH-pyrazole-4 carbothioamide, (2.049) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-i-methyl-iH pyrazole-4-carboxamide, (2.050) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(5-fluoro-2 isopropylbenzyl)-i-methyl-iH-pyrazole-4-carboxamide, (2.051) N-cyclopropyl-3-(difluoromethyl)-N-(2 ethyl-4,5-dimethylbenzyl)-5-fluoro-i-methyl-iH-pyrazole-4-carboxamide, (2.052) N-cyclopropyl-3 (difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-i-methyl-iH-pyrazole-4-carboxamide, (2.053) N cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluoro-i-methyl-iH-pyrazole-4 carboxamide, (2.054) N-cyclopropyl-N-(2-cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro-1 methyl-IH-pyrazole-4-carboxamide, (2.055) N-cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-

(difluoromethyl)-5-fluoro-1-methyl-IH-pyrazole-4-carboxamide, (2.056) N-cyclopropyl-N-(2 cyclopropylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-IH-pyrazole-4-carboxamide.

3) Inhibitors of the respiratory chain at complex III, for example (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-[({[(iE)-1-(3-{[(E)-1-fluoro-2 phenylvinyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.022) (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3 enamide, (3.023) (2R)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3.024) (2S)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (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-methylpropanoate, (3.026) 2-{2-[(2,5 dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3.027) N-(3-ethyl-3,5,5 trimethylcyclohexyl)-3-formamido-2-hydroxybenzamide, (3.028) (2E,3Z)-5-{[1-(4-chloro-2 fluorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (3.029) methyl {5

[3-(2,4-dimethylphenyl)-1H-pyrazol-1-yl]-2-methylbenzyl}carbamate.

4) Mitosis and cell division inhibitors, for example (4.001) carbendazim, (4.002) diethofencarb, (4.003) ethaboxam, (4.004) fluopicolid, (4.005) pencycuron, (4.006) thiabendazole, (4.007) thiophanate-methyl, (4.008) zoxamide, (4.009) 3-chloro-4-(2,6-difluorophenyl)-6-methyl-5-phenylpyridazine, (4.010) 3-chloro 5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine, (4.011) 3-chloro-5-(6-chloropyridin-3-yl) 6-methyl-4-(2,4,6-trifluorophenyl)pyridazine, (4.012) 4-(2-bromo-4-fluorophenyl)-N-(2,6-difluorophenyl) 1,3-dimethyl-1H-pyrazol-5-amine, (4.013) 4-(2-bromo-4-fluorophenyl)-N-(2-bromo-6-fluorophenyl)-1,3 dimethyl-1H-pyrazol-5-amine, (4.014) 4-(2-bromo-4-fluorophenyl)-N-(2-bromophenyl)-1,3-dimethyl-iH pyrazol-5-amine, (4.015) 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-iH pyrazol-5-amine, (4.016) 4-(2-bromo-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5 amine, (4.017) 4-(2-bromo-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.018) 4-(2-chloro-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.019) 4-(2 chloro-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.020) 4-(2 chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.021) 4-(2-chloro-4 fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.022) 4-(4-chlorophenyl)-5-(2,6 difluorophenyl)-3,6-dimethylpyridazine, (4.023) N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4-fluorophenyl) 1,3-dimethyl-1H-pyrazol-5-amine, (4.024) N-(2-bromophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl 1H-pyrazol-5-amine, (4.025) N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl 1H-pyrazol-5-amine.

5) Compounds having capacity for multi-site activity, for example (5.001) Bordeaux mixture, (5.002) captafol, (5.003) captan, (5.004) chlorthalonil, (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.

6) Compounds capable of triggering host defence, for example (6.001) acibenzolar-S-methyl, (6.002) isotianil, (6.003) probenazole, (6.004) tiadinil.

7) Amino acid and/or protein biosynthesis inhibitors, 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-dihydroisoquinolin-1-yl)quinoline.

(8) ATP production inhibitors, for example (8.001) silthiofam.

9) Cell wall synthesis inhibitors, 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.

10) Lipid and membrane synthesis inhibitors, for example (10.001) propamocarb, (10.002) propamocarb hydrochloride, (10.003) tolclofos-methyl.

11) Melanin biosynthesis inhibitors, for example (11.001) tricyclazole, (11.002) 2,2,2-trifluoroethyl {3 methyl-i-[(4-methylbenzoyl)amino]butan-2-yl}carbamate.

12) Nucleic acid synthesis inhibitors, for example (12.001) benalaxyl, (12.002) benalaxyl-M (kiralaxyl), (12.003) metalaxyl, (12.004) metalaxyl-M (mefenoxam).

13) Signal transduction inhibitors, for example (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazid, (13.005) quinoxyfen, (13.006) vinclozolin.

14) Compounds that can act as uncouplers, for example (14.001) fluazinam, (14.002) meptyldinocap.

15) Further compounds, for example (15.001) abscisic acid, (15.002) benthiazole, (15.003) bethoxazin, (15.004) capsimycin, (15.005) carvone, (15.006) chinomethionat, (15.007) cufraneb, (15.008) cyflufenamid, (15.009) cymoxanil, (15.010) cyprosulfamide, (15.011) flutianil, (15.012) fosetyl-aluminium, (15.013) fosetyl-calcium, (15.014) fosetyl-sodium, (15.015) methyl isothiocyanate, (15.016) metrafenon, (15.017) mildiomycin, (15.018) natamycin, (15.019) nickel dimethyldithiocarbamate, (15.020) nitrothal-isopropyl, (15.021) oxamocarb, (15.022) oxathiapiprolin, (15.023) oxyfenthiin, (15.024) pentachlorophenol and salts,

(15.025) phosphonic acid and salts thereof, (15.026) propamocarb-fosetylate, (15.027) pyriofenone (chlazafenone), (15.028) tebufloquin, (15.029) tecloftalam, (15.030) tolnifanide, (15.031) 1-(4-{4-[(5R)-5 (2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-l-yl)-2-[5-methyl-3 (trifluoromethyl)-1H-pyrazol-1-yl]ethanone, (15.032) 1-(4-{4-[(5S)-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, (15.033) 2-(6-benzylpyridin-2-yl)quinazoline, (15.034) 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3 c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetrone, (15.035) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4 {5-[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (15.036) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl] 4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (15.037) 2-[3,5 bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-fluoro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2 oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (15.038) 2-[6-(3-fluoro-4-methoxyphenyl)-5 methylpyridin-2-yl]quinazoline, (15.039) 2-{(5R)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1 yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate, (15.040) 2-{(5S)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4 yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate, (15.041) 2-{2-[(7,8-difluoro-2 methylquinolin-3-yl)oxy]-6-fluorophenyl}propan-2-ol, (15.042) 2-{2-fluoro-6-[(8-fluoro-2 methylquinolin-3-yl)oxy]phenyl}propan-2-ol, (15.043) 2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol 1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate, (15.044) 2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl) 1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl methanesulfonate, (15.045) 2-phenylphenol and salts thereof, (15.046) 3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, (15.047) 3-(4,4 difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, (15.048) 4-amino-5-fluoropyrimidin-2-ol (tautomeric form: 4-amino-5-fluoropyrimidin-2(1H)-one), (15.049) 4-oxo-4-[(2-phenylethyl)amino]butyric acid, (15.050) 5-amino-1,3,4-thiadiazole-2-thiol, (15.051) 5-chloro-N'-phenyl-N'-(prop-2-yn-1-yl)thiophene 2-sulfonohydrazide, (15.052) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidin-4-amine, (15.053) 5-fluoro-2-[(4 methylbenzyl)oxy]pyrimidin-4-amine, (15.054) 9-fluoro-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro-1,4 benzoxazepine, (15.055) but-3-yn-1-yl {6-[({[(Z)-(1-methyl-iH-tetrazol-5 yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl} carbamate, (15.056) ethyl (2Z)-3-amino-2-cyano-3 phenylacrylate, (15.057) phenazine-1-carboxylic acid, (15.058) propyl 3,4,5-trihydroxybenzoate, (15.059) quinolin-8-ol, (15.060) quinolin-8-ol sulfate (2:1), (15.061) tert-butyl{6-[({[(1-methyl-H-tetrazol-5 yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate, (15.062) 5-fluoro-4-imino-3-methyl-i

[(4-methylphenyl)sulfonyl]-3,4-dihydropyrimidin-2(lH)-one. Insecticidally active compounds are, for example:

(1) Acetylcholinesterase (AChE) inhibitors, for example carbamates, e.g. 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 and xylylcarb; or organophosphates, e.g. acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chloropyrifos, chloropyrifos-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 0 (methoxyaminothiophosphoryl) salicylate, 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 and vamidothion.

(2) GABA-gated chloride channel antagonists, for example cyclodiene-organochlorines, e.g. chlordane and endosulfan or phenylpyrazoles (fiproles), e.g. ethiprole and fipronil.

(3) Sodium channel modulators/voltage-gated sodium channel blockers, for example 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)-(R) isomers], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, momfluorothrin, permethrin, phenothrin [(R)-trans isomer], prallethrin, pyrethrins (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(iR) isomers)], tralomethrin and transfluthrin or DDT or methoxychlor.

(4) Nicotinergic acetylcholine receptor (nAChR) agonists, for example neonicotinoids, e.g. acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor or flupyradifurone.

(5) Nicotinergic acetylcholine receptor (nAChR) allosteric activators, for example spinosyns, e.g. spinetoram and spinosad.

(6) Chloride channel activators, for example avermectins/milbemycins, e.g. abamectin, emamectin benzoate, lepimectin and milbemectin.

(7) Juvenile hormone mimics, for example, juvenile hormone analogues, e.g. hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen.

(8) Active compounds with unknown or non-specific mechanisms of action, for example alkyl halides, e.g. methyl bromide and other alkyl halides; or chloropicrin or sulfuryl fluoride or borax or tartar emetic.

(9) Selective antifeedants, e.g. pymetrozine or flonicamid.

(10) Mite growth inhibitors, e.g. clofentezine, hexythiazox and diflovidazin or etoxazole.

(11) Microbial disruptors of insect midgut membranes, e.g. Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis, and BT plant proteins: CrylAb, CrylAc, CrylFa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34/35Abl.

(12) Oxidative phosphorylation inhibitors, ATP disruptors, for example diafenthiuron or organotin compounds, e.g. azocyclotin, cyhexatin and fenbutatin oxide or propargite or tetradifon.

(13) Uncouplers of oxidative phosphorylation via disruption of the H proton gradient, for example chlorfenapyr, DNOC and sulfluramid.

(14) Nicotinergic acetylcholine receptor antagonists, for example bensultap, cartap hydrochloride, thiocyclam, and thiosultap-sodium.

(15) Inhibitors of chitin biosynthesis, type 0, for example bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.

(16) Inhibitors of chitin biosynthesis, type 1, for example buprofezin.

(17) Moulting disruptors, dipteran, for example cyromazine.

(18) Ecdysone receptor agonists, for example chromafenozide, halofenozide, methoxyfenozide and tebufenozide.

(19) Octopaminergic agonists, for example amitraz.

(20) Complex III electron transport inhibitors, for example hydramethynon or acequinocyl or fluacrypyrim.

(21) Complex I electron transport inhibitors, for example METI acaricides, e.g. fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad or rotenone (Derris).

(22) Voltage-gated sodium channel blockers, for example indoxacarb or metaflumizone.

(23) Inhibitors of acetyl-CoA carboxylase, for example tetronic and tetramic acid derivatives, e.g. spirobudiclofen, spirodiclofen, spiromesifen and spirotetramat.

(24) Complex IV electron transport inhibitors, for example phosphines, e.g. aluminium phosphide, calcium phosphide, phosphine and zinc phosphide or cyanide.

(25) Complex II electron transport inhibitors, for example cyenopyrafen and cyflumetofen.

(28) Ryanodine receptor effectors, for example diamides, e.g. chlorantraniliprole, cyantraniliprole, flubendiamide and tetrachloroantraniliprole.

Further insecticidally active compounds having an unknown or unclear mechanism of action, for example afidopyropen, afoxolaner, azadirachtin, benclothiaz, benzoximate, bifenazate, broflanilide, bromopropylate, chinomethionat, cryolite, cyclaniliprole, cycloxaprid, cyhalodiamide, dicloromezotiaz, dicofol, diflovidazin, flometoquin, fluazaindolizine, fluensulfone, flufenerim, flufenoxystrobin, flufiprole, fluhexafon, fluopyram, fluralaner, fluxametamide, fufenozide, guadipyr, heptafluthrin, imidaclothiz, iprodione, lotilaner, meperfluthrin, paichongding, pyflubumide, pyridalyl, pyrifluquinazon, pyriminostrobin, sarolaner, tetramethylfluthrin, tetraniliprole, tetrachlorantraniliprole, tioxazafen, thiofluoximate, triflumezopyrim and iodomethanes; and additionally preparations based on Bacillus firmus (1-1582, BioNeem, Votivo), and the following known active compounds: 1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulphinyl]phenyl}-3 (trifluoromethyl)-1H-1,2,4-triazole-5-amine (known from W02006/043635), {1'-[(2E)-3-(4 chlorophenyl)prop-2-en-1-yl]-5-fluorospiro[indole-3,4'-piperidin]-1(2H)-yl}(2-chloropyridin-4 yl)methanone (known from W02003/106457), 2-chloro-N-[2-{l-[(2E)-3-(4-chlorophenyl)prop-2-en-1 yl]piperidin-4-yl}-4-(trifluoromethyl)phenyl]isonicotinamide (known from W02006/003494), 3-(2,5 dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one (known from W02009/049851), 3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-ylethyl carbonate (known from W02009/049851), 4-(but-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5 fluoropyrimidine (known from W02004/099160), 4-(but-2-yn-1-yloxy)-6-(3-chlorophenyl)pyrimidine (known from W02003/076415), 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 methylhydrazinecarboxylate (known from W02005/085216), methyl 2-[2-({[3-bromo-1-(3-chloropyridin 2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-cyano-3-methylbenzoyl]-2-ethylhydrazinecarboxylate (known from W02005/085216), methyl 2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5 yl]carbonyl}amino)-5-cyano-3-methylbenzoyl]-2-methylhydrazinecarboxylate (known from W02005/085216), methyl 2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5 yl]carbonyl}amino)benzoyl]-2-ethylhydrazinecarboxylate (known from W02005/085216), N-[2-(5-amino 1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5 carboxamide (known from CN102057925), 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2 oxazol-3-yl]-2-methyl-N-(1-oxidothietan-3-yl)benzamide (known from W02009/080250), N-[(2E)-1-[(6 chlorpyridin-3-yl)methyl]pyridin-2(H)-yliden]-2,2,2-trifluoracetamid (known from W02012/029672), 1

[(2-chloro-1,3-thiazol-5-yl)methyl]-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-ium-2-olate (known from W02009/099929), 1-[(6-chloropyridin-3-yl)methyl]-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1 ium-2-olate (known from W02009/099929), 4-(3-{2,6-dichloro-4-[(3,3-dichloroprop-2-en-1 yl)oxy]phenoxy}propoxy)-2-methoxy-6-(trifluoromethyl)pyrimidine (known from CN101337940), N-[2 (tert-butylcarbamoyl)-4-chloro-6-methylphenyl]-1-(3-chloropyridin-2-yl)-3-(fluoromethoxy)-1H-pyrazole 5-carboxamide (known from W02008/134969), butyl 2-(2,4-dichlorophenyl)-3-oxo-4-oxaspiro[4.5]dec-1- en-1-yl carbonate (known from CN 102060818), 3E)-3-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene] 1,1,1-trifluoropropan-2-one (known from W02013/144213), N-(methylsulfonyl)-6-[2-(pyridin-3-yl)-1,3 thiazol-5-yl]pyridine-2-carboxamide (known from W02012/000896), N-[3-(benzylcarbamoyl)-4 chlorophenyl]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide (known from W02010/051926), 5-bromo-4-chloro-N-[4-chloro-2-methyl-6-(methylcarbamoyl)phenyl]-2-(3 chloro-2-pyridyl)pyrazole-3-carboxamide (known from CN103232431), tioxazafen, 4-[5-(3,5 dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxido-3 thietanyl)benzamide, 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N (trans-I-oxido-3-thietanyl)-benzamideand4-[(5S)-5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl) 3-isoxazolyl]-2-methyl-N-(cis-1-oxido-3-thietanyl)benzamide (known from WO 2013050317 A1), N-[3 chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propanamide, (+)-N-[3 chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propanamide and (-)-N

[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]propanamide (known from WO 2013162715 A2, WO 2013162716 A2, US 20140213448 Al), 5-[[(2E)-3-chloro-2-propen-1 yl]amino]-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3 carbonitrile (known from CN 101337937 A), 3-bromo-N-[4-chloro-2-methyl-6

[(methylamino)thioxomethyl]phenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide, (liudaibenjiaxuanan, known from CN 103109816 A); N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl] 6-methylphenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide (known from WO 2012034403 Al), N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3 chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide (known from WO 2011085575 Al), 4-[3-[2,6-dichloro-4

[(3,3-dichloro-2-propen-1-yl)oxy]phenoxy]propoxy]-2-methoxy-6-(trifluoromethyl)pyrimidine (known from CN 101337940 A); (2E)- and 2(Z)-2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N

[4-(difluoromethoxy)phenyl]hydrazinecarboxamide (known from CN 101715774 A); 3-(2,2 dichloroethenyl)-2,2-dimethyl-4-(1H-benzimidazol-2-yl)phenylcyclopropanecarboxylicacidester(known from CN 103524422 A); methyl (4aS)-7-chloro-2,5-dihydro-2-[[(methoxycarbonyl)[4

[(trifluoromethyl)thio]phenyl]amino]carbonyl]indeno[1,2-e][1,3,4]oxadiazine-4a(3H)carboxylate (known from CN 102391261 A).

Examples of herbicidal mixing partners are:

acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3 methylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor potassium, 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 and -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, cinmethylin, cinosulfuron, clacyfos, clethodim, clodinafop, clodinafop-propargyl, clomazone, clomeprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D-butotyl, -butyl, dimethylammonium, -diolamine, -ethyl, -2-ethylhexyl, -isobutyl, -isooctyl, -isopropylammonium, potassium, -triisopropanolammonium and -trolamine, 2,4-DB, 2,4-DB-butyl, -dimethylammonium, isooctyl, -potassium and -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, diflufenican, diflufenzopyr, diflufenzopyr sodium, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimetrasulfuron, dinitramine, dinoterb, diphenamid, diquat, diquat dibromide, 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-chloro 4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]phenyl]ethansulfonamide, F-7967, i.e. 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6 (trifluoromethyl)pyrimidine-2,4(1H,3H)-dione, 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, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, dimethylammonium and -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 and -trimesium, H-9201, i.e. 0-(2,4-dimethyl-6-nitrophenyl) O-ethyl isopropylphosphoramidothioate, 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 dichlorophenoxy)acetate,imazamethabenz,imazamethabenz-methyl,imazamox,imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquin ammonium, imazethapyr, imazethapyr-immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxynil-octanoate, -potassium and -sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, karbutilate, KUH-043, i.e. 3-({[5-(difluoromethyl)-1-methyl-

3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole, ketospiradox, lactofen, lenacil, linuron, MCPA, MCPA-butotyl, -dimethylammonium, -2-ethylhexyl, isopropylammonium, -potassium and -sodium, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-sodium and -butotyl, mecoprop-P, mecoprop-P-butotyl, -dimethylammonium, -2-ethylhexyl and -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, molinate, monolinuron, monosulfuron, monosulfuron-ester, MT-5950, i.e. N-[3-chloro-4-(1-methylethyl)phenyl]-2 methylpentanamide, NGGC-011, napropamide, NC-310, i.e. 4-(2,4-dichlorobenzoyl)-1-methyl-5 benzyloxypyrazole, neburon, nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, 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, pyroxasulfone, 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--oxobut-3-en-2-yl 5-[2-chloro-4 (trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP-300, i.e. 1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4 dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidine-4,5-dione, 2,3,6-TBA, TCA (trifluoroacetic acid), TCA-sodium, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazin, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone methyl, 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-dichloro-N-{2

[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline, and also the following compounds:

0 O0

N N N AC /IOHN 0 U / 0 O CF OH 0 1O 0

0

O F

CF3 / N CI NN

0 \-CO 2 Et

Examples of plant growth regulators as possible mixing partners are:

acibenzolar, acibenzolar-S-methyl, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, brassinolide, catechol, 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, flumetralin, flurenol, flurenol-butyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid (IAA), 4-indol-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, paclobutrazole, N-phenylphthalamic acid, prohexadione, prohexadione-calcium, prohydrojasmone, salicylic acid, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P.

Most preferably, component a) is combined with an active compound d) from the group of the herbicides, preferably from the group of the auxins, for instance halauxifen-methyl (0.05%-5% by weight) and/or from the group of the inhibitors of pigment synthesis (pigment bleachers), for instance diflufenican 5-30% and from the group of the DOXP synthase inhibitors, for instance clomazone, and/or from the group of the VLCFA inhibitors ("very long chain fatty acid", inhibition of cell division for production of fatty acids) flufenacet (5%-30% by weight) or pyroxasulfones. Preference is given to using flufenacet and/or diflufenican.

In addition, the SCs according to the invention can contain a safener e). The following groups of compounds, for example, are suitable as safeners (component e):

Si) Compounds from the group of heterocyclic carboxylic acid derivatives:

Sl) Compounds of the dichlorophenylpyrazoline-3-carboxylic acid type (SIa), preferably compounds such as

1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylic acid, ethyl 1-(2,4 dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate (Si-1) ("mefenpyr diethyl"), and related compounds as described in WO-A-91/07874;

Slb) Derivatives of dichlorophenylpyrazolecarboxylic acid (SIb), preferably compounds such as ethyl 1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate (Si-2), ethyl 1-(2,4-dichlorophenyl)-5 isopropylpyrazole-3-carboxylate (Si-3), ethyl 1-(2,4-dichlorophenyl)-5-(ii dimethylethyl)pyrazole-3-carboxylate (Si-4) and related compounds as described in EP-A-333 131 and EP-A-269 806;

Si°) Derivatives of 1,5-diphenylpyrazole-3-carboxylic acid (Sic), preferably compounds such as ethyl 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate (Si-5), methyl 1-(2-chlorophenyl)-5 phenylpyrazole-3-carboxylate (S-6) and related compounds as described, for example, in EP-A 268554;

Sid) Compounds of the triazolecarboxylic acids type (Sid), preferably compounds such as fenchlorazole (ethyl ester), i.e. ethyl 1-(2,4-dichlorophenyl)-5-trichloromethyl-(iH)-1,2,4-triazole 3-carboxylate (Si-7), and related compounds as described in EP-A-174 562 and EP-A-346 620;

Sl°) Compounds of the 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid or of the 5,5-diphenyl-2 isoxazoline-3-carboxylic acid type (Sle), preferably compounds such as ethyl 5-(2,4 dichlorobenzyl)-2-isoxazoline-3-carboxylate (Si-8) or ethyl 5-phenyl-2-isoxazoline-3-carboxylate (Si-9) and related compounds as described in WO-A-91/08202, or 5,5-diphenyl-2 isoxazolinecarboxylic acid (SI-10) or ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (SI-11) ("isoxadifen-ethyl") or n-propyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (SI-12) or ethyl 5-(4 fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (S-13) as described in patent application WO-A-95/07897.

S2) Compounds from the group of the 8-quinolinoxy derivatives (S2):

S2a) Compounds of the 8-quinolinoxyacetic acid type (S2a), preferably i-methylhexyl (5-chloro-8 quinolinoxy)acetate ("cloquintocet-mexyl") (S2-1), 1,3-dimethylbut-1-yl (5-chloro-8 quinolinoxy)acetate (S2-2), 4-allyloxybutyl (5-chloro-8-quinolinoxy)acetate (S2-3), I allyloxyprop-2-yl (5-chloro-8-quinolinoxy)acetate (S2-4), ethyl (5-chloro-8-quinolinoxy)acetate (S2-5), methyl (5-chloro-8-quinolinoxy)acetate (S2-6), allyl (5-chloro-8-quinolinoxy)acetate (S2 7), 2-(2-propylideneiminoxy)-I-ethyl (5-chloro-8-quinolinoxy)acetate (S2-8), 2-oxoprop-I-yl (5 chloro-8-quinolinoxy)acetate (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, and also (5-chloro-8-quinolinoxy)acetic acid (S2 10), hydrates and salts thereof, for example the lithium, sodium, potassium, calcium, magnesium, aluminium, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts thereof, as described in WO-A-2002/34048;

S2b) Compounds of the (5-chloro-8-quinolinoxy)malonic acid type (S2), preferably compounds such as diethyl (5-chloro-8-quinolinoxy)malonate, diallyl (5-chloro-8-quinolinoxy)malonate, methyl ethyl (5-chloro-8-quinolinoxy)malonate and related compounds, as described in EP-A-0 582 198.

S3) Active compounds of the dichloroacetamide type (S3), which are frequently used as pre emergence safeners (soil-acting safeners), for example "dichlormid" (N,N-diallyl-2,2-dichloroacetamide) (S3-1), "R-29148" (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) from Stauffer (S3-2), "R-28725" (3-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine) from Stauffer (S3-3), "benoxacor" (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4), "PPG-1292" (N-allyl-N-[(1,3-dioxolan-2-yl)methyl]dichloroacetamide) from PPG Industries (S3

5), "DKA-24" (N-allyl-N-[(allylaminocarbonyl)methyl]dichloroacetamide) from Sagro-Chem (S3-6), "AD-67" or "MON 4660" (3-dichloroacetyl-1-oxa-3-azaspiro[4.5]decane) from Nitrokemia or Monsanto (S3-7), "TI-35" (1-dichloroacetylazepane) from TRI-Chemical RT (S3-8), "diclonon" (dicyclonon) or "BAS145138" or "LAB145138" (S3-9) ((RS)-1-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo[1,2-a]pyrimidin-6-one) from BASF, "furilazole" or "MON 13900" ((RS)-3-dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidine) (S3 10), and the (R) isomepr thereof (S3-11). S4) Compounds from the class of the acylsulfonamides (S4):

S4 ) N-Acylsulfonamides of the formula (S4a) and salts thereof, as described in WO-A-97/45016,

0 0 0 (RA 2 )mA )-N -0 S-N -L- I / (W4) R1 I II A H O H

in which

RA 1 represents (CI-C6 )-alkyl, (C 3- 6)-cycloalkyl, where the 2 latter radicals are substituted by vA

substituents from the group of halogen, (C-C4)-alkoxy, (C-C 6)-haloalkoxy and (C-C 4)-alkylthio

and, in the case of cyclic radicals, also by (C-C 4)-alkyl and (C-C 4)-haloalkyl;

RA 2 represents halogen, (C-C 4)-alkyl, (C-C4)-alkoxy, CF3 ; mA represents I or 2;

VA represents 0, 1, 2 or 3;

S4) Compounds of the 4-(benzoylsulfamoyl)benzamide type of the formula (S4) and salts thereof, as described in WO-A-99/16744,

R 1 iB 0 0 3 2/N 11 (RB mB RB /S-N /- (SOb) 0 0 H

in which

RB1 , RB 2 independently of one another represent hydrogen, (C-C)-alkyl, (C 3-C)-cycloalkyl, (C 3-C 6)-alkenyl, (C3-C6)-alkynyl,

3 RB represents halogen, (CI-C 4 )-alkyl, (CI-C4)-haloalkyl or (C-C 4 )-alkoxy and

mB represents I or 2,

e.g. those in which

RB 1 = cyclopropyl, RB 2 = hydrogen and (RB 3) = 2-OMe ("cyprosulfamide", S4-1),

RB 1 = cyclopropyl, RB 2 = hydrogen and (RB 3) = 5-Cl-2-OMe (S4-2),

RB 1 = ethyl, RB 2 = hydrogen and (RB 3) = 2-OMe (S4-3),

RB 1 = isopropyl, RB2 = hydrogen and (RB 3) = 5-Cl-2-OMe (S4-4) and

RB 1 = isopropyl, RB2 = hydrogen and (RB 3) = 2-OMe (S4-5);

S4°) Compounds from the class of the benzoylsulfamoylphenylureas of the formula (S4),as described in EP-A-365484,

R0 0 0 (R C3 )MC c N N (Rc S-N (S4c) Rc H O H

in which

RcI, Rc 2 independently represent hydrogen, (C-C)-alkyl, (C 3-C)-cycloalkyl, (C 3-C) alkenyl, (C 3-C6 )-alkynyl,

Rc 3 represents halogen, (C-C 4 )-alkyl, (C-C4)-alkoxy, CF3 and

mc represents 1 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) Compounds of the N-phenylsulfonylterephthalamide type of the formula (S4) and salts thereof, which are known, for example, from CN 101838227,

5 R iD0 04 HN1 HN-S /' mD (R D)moD (SOd)a

0 H O

in which

RD 4 represents halogen, (C-C4 )-alkyl, (C-C 4)-alkoxy, CF3 ;

mD represents I or 2;

RD 5 represents hydrogen, (C-C)-alkyl, (C 3-C)-cycloalkyl, (C 2 -C)-alkenyl, (C2-C)-alkynyl,

(Cs-C6)-cycloalkenyl.

S5) Active compounds from the class of the hydroxyaromatics and the aromatic-aliphatic carboxylic acid derivatives (S5), for example ethyl 3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicylic 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 compounds from the class of the 1,2-dihydroquinoxalin-2-ones (S6), for example 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one, 1-methyl-3-(2-thienyl)-1,2 dihydroquinoxaline-2-thione, 1-(2-aminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one hydrochloride, 1-(2-methylsulfonylaminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one, as described in WO-A-2005/112630.

S7) Compounds from the class of the diphenylmethoxyacetic acid derivatives (S7), e.g. methyl diphenylmethoxyacetate (CAS Reg. No. 41858-19-9) (S7-1), ethyl diphenylmethoxyacetate or diphenylmethoxyacetic acid, as described in WO-A-98/38856.

S8) Compounds of the formula (S8), as described in WO-A-98/27049,

R20 RD20 R3

O' ° (S8) F

in which the symbols and indices are defined as follows:

RD' represents halogen, (C-C 4 )-alkyl, (C-C4)-haloalkyl, (C-C 4)-alkoxy, (C-C4)-haloalkoxy,

RD2 represents hydrogen or (C1-C4 )-alkyl,

RD 3 represents hydrogen, (CI-Cg)-alkyl, (C 2 -C 4 )-alkenyl, (C2-C 4 )-alkynyl or aryl, where each of the aforementioned carbon-containing radicals is unsubstituted or substituted by one or more, preferably up to three, identical or different radicals from the group consisting of halogen and alkoxy; or salts thereof,

nD represents an integer from 0 to 2.

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

S10) Compounds of the formula (S10a) or (S10b)

as described in WO-A-2007/023719 and WO-A-2007/023764

0 ZE E 3 0 1 (R E )fE 5-N HYERE2(RE (EnE/N YERE2 E )nnE 0 0

O S-N YERE

(S1a) (S1 0b in which

RE' represents halogen, (CI-C 4 )-alkyl, methoxy, nitro, cyano, CF3 ,OCF 3

, YE, ZE independently of one another represent 0 or S,

nE represents an integer from 0 to 4,

RE represents (CI-Ci 6 )-alkyl, (C2 -C6 )-alkenyl, (C 3-C 6)-cycloalkyl, aryl; benzyl, halobenzyl,

RE 3 represents hydrogen or(C-C 6)-alkyl.

Si1) Active compounds of the oxyimino compounds type (S11), which are known as seed-dressing agents, for example

"oxabetrinil" ((Z)-1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (S11-1), which is known as a seed-dressing safener for millet/sorghum against metolachlor damage,

"fluxofenim" (1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethanone O-(1,3-dioxolan-2-ylmethyl)oxime) (S1 1-2), which is known as a seed-dressing safener for millet/sorghum against metolachlor damage, and

"cyometrinil" or "CGA-43089" ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (S11-3), which is known as a seed-dressing safener for millet/sorghum against metolachlor damage.

S12) Active compounds from the class of the isothiochromanones (S12), for example methyl [(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), which is known as a seed-dressing safener for corn against thiocarbamate herbicide damage,

"fenclorim" (4,6-dichloro-2-phenylpyrimidine) (S13-2), which is known as a safener for pretilachlor in sown rice,

"flurazole" (benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) (S13-3), which is known as a seed-dressing safener for millet/sorghum against alachlor and metolachlor damage,

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

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

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

"disulfoton" (0,0-diethyl S-2-ethylthioethyl phosphorodithioate) (S13-7),

"dietholate" (0,0-diethyl O-phenyl phosphorothioate) (S13-8),

"mephenate" (4-chlorophenyl methylcarbamate) (S13-9).

S14) Active compounds which, in addition to herbicidal action against harmful plants, also have safener action on crop plants such as rice, for example "dimepiperate" or "MY-93" (S-I-methyl 1-phenylethylpiperidine-1-carbothioate), which is known as a safener for rice against damage by the herbicide molinate,

"daimuron" or "SK 23" (1-(1-methyl-1-phenylethyl)-3-p-tolylurea), which is known as a safener for rice against damage by the herbicide imazosulfuron,

"cumyluron" = "JC-940" (3-(2-chlorophenylmethyl)-1-(1-methyl-i-phenylethyl)urea, see JP-A 60087254), which is known as a safener for rice against damage by some herbicides,

"methoxyphenone" or "NK 049" (3,3'-dimethyl-4-methoxybenzophenone), which is known as a safener for rice against damage by some herbicides,

"CSB" (1-bromo-4-(chloromethylsulfonyl)benzene) from Kumiai, (CAS Reg. No. 54091-06-4), which is known as a safener against damage by some herbicides in rice.

S15) Compounds of the formula (S15) or tautomers thereof 0 R H2 NR H4 H N/ H | 3 (S15) 1 R RH N O H H H as described in WO-A-2008/131861 and WO-A-2008/131860,

in which

1 RH represents a (CI-C 6)-haloalkyl radical and

2 RH represents hydrogen or halogen and

3 4 RH , RH independently of one another represent hydrogen, (C-Ci 6 )-alkyl, (C 2 -Ci 6 )-alkenyl or (C2-Ci 6)-alkynyl,

where each of the 3 last-mentioned radicals is unsubstituted or substituted by one or more radicals from the group of halogen, hydroxyl, cyano, (C-C 4)-alkoxy, (C-C4)-haloalkoxy, (CI-C 4)-alkylthio, (CI-C4)-alkylamino, di[(C-C 4 )-alkyl]amino, [(C1-C 4)-alkoxy]carbonyl,

[(CI-C 4)-haloalkoxy]carbonyl, (C 3 -C)-cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, and heterocyclyl which is unsubstituted or substituted,

or (C 3-C)-cycloalkyl, (C4-C)-cycloalkenyl, (C 3-C)-cycloalkyl fused on one side of the ring to a 4 to 6-membered saturated or unsaturated carbocyclic ring, or (C4-C6)-cycloalkenyl fused on one side of the ring to a 4 to 6-membered saturated or unsaturated carbocyclic ring,

where each of the 4 latter radicals is unsubstituted or substituted by one or more radicals from the group of halogen, hydroxyl, cyano, (C-C4 )-alkyl, (C-C 4 )-haloalkyl, (C-C 4 ) alkoxy, (CI-C 4)-haloalkoxy, (CI-C 4)-alkylthio, (CI-C 4)-alkylamino, di[(C1 -C 4 ) alkyl]amino, [(CI-C 4)-alkoxy]carbonyl, [(C1-C4)-haloalkoxy]carbonyl, (C 3-C6)-cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, and heterocyclyl which is unsubstituted or substituted,

or

RH 3 represents (Ci-C 4)-alkoxy, (C2-C 4)-alkenyloxy, (C2-C 6)-alkynyloxy or (C 2-C 4)-haloalkoxy and

4 RH represents hydrogen or (CI-C4 )-alkyl or

RH 3 and RH together with the directly attached nitrogen atom represent a four- to eight-membered heterocyclic ring which, as well as the nitrogen atom, may also contain further ring heteroatoms, preferably up to two further ring heteroatoms from the group of N, 0 and S, and which is unsubstituted or substituted by one or more radicals from the group of halogen, cyano, nitro, (C1 C 4)alkyl, (CI-C4)haloalkyl, (CI-C 4)alkoxy, (CI-C4)haloalkoxy and (C-C 4)alkylthio.

S16) Active compounds which are used primarily as herbicides but also have safener action on crop plants, for example

(2,4-dichlorophenoxy)acetic acid (2,4-D), (4-chlorophenoxy)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-chlorophenoxy)butyric acid, 3,6-dichloro-2-methoxybenzoic acid (dicamba), 1-(ethoxycarbonyl)ethyl 3,6-dichloro-2-methoxybenzoate (lactidichlor-ethyl).

Preferred safeners for the purposes of the present invention are safeners based on the esters of cloquintocet (preferably mexyl ester) and/or mefenpyr (preferably as diethyl ester), particularly preferably mefenpyr diethyl ester.

Preferred thickeners f) are organic thickeners, which may be natural or biotechnologically modified or organically synthetic thickeners.

Typical synthetic thickeners are Rheostrux@ (Croda), Thixin@ or Thixatrol@ series (Elementis). These are typically based on acrylates. Typical organic thickeners are based on xanthan or cellulose (for instance hydroxyethyl or carboxymethyl cellulose) or a combination thereof. Preference is given to using natural modified thickeners based on xanthan. Typical representatives are, for example, Rhodopol@ (Solvay) and Kelzan@ (Kelco Corp.), and also Satiaxane@ (Cargill).

Other additives and auxiliaries g) are wetting agents, pH adjusters, defoamers, biocides, disintegrants, adhesion promoters, antifreeze agents, preservatives, dyes or fertilizers, as well as surfactants different from component b) and fillers different from c); preference is given to adding antifreeze agents, defoamers and biocides.

Suitable defoamers are surface-active silicone- or silane-based compounds such as the Tegopren@ products (Goldschmidt), the SE@ products (Wacker), and the Bevaloid® (Kemira), Rhodorsil® (Solvay) and Silcolapse@ products (Blustar Silicones), preference being given to SE@ (Wacker), Rhodorsil@ and Silcolapse@ products, particular preference, for example, to products such as Silcolapse® 5020.

Suitable antifreezes are those from the group of the ureas, diols and polyols, such as ethylene glycol and propylene glycol, glycerol, preferably propylene glycol or glycerol.

Suitable biocides are, for example, products such as Acticide® MBS (Biozid, Thor Chemie), CIT, MIT or BIT, for instance Proxel® GXL (BIT), Acticide® SPX (MIT, CIT).

Suitable adhesion promoters may be selected from the group of polyvinylpyrrolidone (PVP), polyvinyl alcohol, copolymer of PVP and dimethylaminoethyl methacrylate, butylated PVP, copolymer of vinyl chloride and vinyl acetate, sodium salt of the copolymer of propenesultanic acid and partially hydrolysed vinyl acetate, sodium caseinate, phenol resins, modified cellulose types, for example Luviskol® (polyvinylpyrrolidone), Mowiol® (polyvinyl alcohol), modified cellulose.

Preference is given to polyvinylpyrrolidone types, particular preference to types of low molecular weight such as Luviskol@ K30.

Suitable disintegrants may be selected from the group of the modified carbohydrates, such as microcrystalline cellulose and crosslinked polyvinylpyrrolidones, for example Avicel@ PH 101 (microcrystalline cellulose), Agrimer@ XLF (crosslinked polyvinylpyrrolidone), Disintex@ 200 (crosslinked polyvinylpyrrolidone). Preference is given to crosslinked polyvinylpyrrolidones, such as Agrimer@ XLF.

Suitable antifoams may be selected from the group of the esters of phosphoric acid 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 the absorbates thereof onto solid carrier material, for example Rhodorsil® 432 (silicone surfactant), butyl phosphate, isobutyl phosphate, n-octanol, Wacker ASP15 (polydimethylsiloxane, absorbed on solid carrier), Antifoam@SE (polydimethylsiloxane). Preference is given to suspoemulsions of hydrophobized silica particles in aqueous emulsion concentrates based on liquid silicone surfactants, such as Antifoam SE (polydimethylsiloxane), and solid antifoams, such as Wacker ASP 15 (polydimethylsiloxane).

The invention further relates to a herbicidal composition which can be produced from the SCs according to the invention by diluting with liquids, preferably water.

It may be advantageous to add further active compounds to the herbicidal compositions thus obtained, preferably agrochemical active compounds (for example as tankmix partners in the form of appropriate formulations) and/or auxiliaries and additives customarily used, for example self-emulsifying oils such as vegetable oils or paraffin oils and/or fertilizers. The present invention therefore also provides such compositions, preferably herbicidal compositions, based on the formulations according to the invention.

A particular embodiment of the invention relates to the use of the herbicidal compositions obtainable from the SCs according to the invention for control of unwanted vegetation, referred to hereinafter as "herbicidal composition".

The herbicidal compositions have excellent herbicidal efficacy against a broad spectrum of economically important mono- and dicotyledonous harmful plants. There is also good control over difficult-to-control perennial weeds which produce shoots from rhizomes, rootstocks or other permanent organs. The herbicidal compositions may be applied, for example, by the pre-sowing, pre-emergence or post-emergence method. Specific examples of some representatives of the monocotyledonous and dicotyledonous weed flora which can be controlled by the herbicidal compositions are mentioned by way of example, though the enumeration is not intended to impose a restriction to particular species.

Examples of weed species which are controlled efficiently are, among the monocotyledonous weed species, Apera spica venti, Avena spp., Alopecurus spp., Brachiaria spp., Digitaria spp., Lolium spp., Echinochloa spp., Panicum spp., Phalaris spp., Poa spp., Setaria spp. and also Bromus spp. such as Bromus catharticus, Bromus secalinus, Bromus erectus, Bromus tectorum and Bromus japonicus and Cyperus species from the annual group, and, among the perennial species, Agropyron, Cynodon, Imperata and Sorghum and also perennial Cyperus species. In the case of dicotyledonous weed species, the spectrum of action extends to species such as, for example, Abutilon spp., Amaranthus spp., Chenopodium spp., Chrysanthemum spp., Galium spp. such as 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., among the annuals, and Convolvulus, Cirsium, Rumex and Artemisia in the case of the perennial weeds.

The herbicidal compositions also have excellent control over weeds that occur under the specific growing conditions that occur in rice, for example Echinochloa, Sagittaria, Alisma, Eleocharis, Scirpus and Cyperus. If the herbicidal compositions are applied to the soil surface before germination, either the weed seedlings are prevented completely from emerging or the weeds grow until they have reached the cotyledon stage, but then stop growing, and eventually, after three to four weeks have elapsed, die completely.

If the herbicidal compositions are applied post-emergence to the green parts of the plants, growth likewise stops drastically a very short time after the treatment, and the weed plants remain in the growth stage at the point of time of application, or they die completely after a certain time, so that in this manner competition by the weeds, which is harmful to the crop plants, is eliminated very early and in a sustained manner.

The herbicidal compositions are notable for a rapid onset and long duration of herbicidal action. The rain resistance of the active compounds in the herbicidal compositions is generally favourable. A particular advantage is that the effective dosages, used in the herbicidal compositions, of herbicidal compounds can be adjusted to such a low level that the soil action thereof is optimally low. Therefore, the use thereof in sensitive crops is not just enabled, but groundwater contamination is also virtually prevented. The combination according to the invention of active compounds allows the required application rate of the active compounds to be reduced considerably.

Said properties and advantages are beneficial in practical weed control in order to keep agricultural crops clear of unwanted competing plants and hence to ensure and/or increase the yields in terms of quality and quantity. The technical standard is markedly improved upon by these novel herbicidal compositions in terms of the properties described.

Even though the herbicidal compositions have excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, there is only insignificant damage, if any, to crop plants of economically important crops, for example dicotyledonous crops such as soya, cotton, oilseed rape, sugar beet, or gramineous crops such as wheat, barley, rye, oats, millet/sorghum, rice or corn. For these reasons, the present herbicidal compositions are of very good suitability for selective control of unwanted plant growth in agriculturally useful plants or in ornamental plants.

Furthermore, the corresponding herbicidal compositions, according to the crop plant, have excellent growth regulating properties. They intervene in the plants' own metabolism with regulatory effect, and can thus be used for the controlled influencing of plant constituents and to facilitate harvesting, for example by triggering desiccation and stunted growth. Furthermore, they are potentially also suitable for the general control and inhibition of unwanted vegetative growth without killing the plants in the process. Inhibition of vegetative growth plays a major role for many mono- and dicotyledonous crops since this can reduce or completely prevent lodging.

By virtue of their herbicidal and plant growth regulatory properties, the herbicidal compositions - as already mentioned - can also be used to control weeds in crops of genetically modified plants which are known or yet to be developed. In general, the transgenic plants are characterized by particular advantageous properties, for example by resistances to certain pesticides, in particular certain herbicides, resistances to plant diseases or pathogens of plant diseases, such as certain insects or microorganisms such as fungi, bacteria or viruses. Other particular properties relate, for example, to the harvested material with regard to quantity, quality, storability, composition and specific constituents. For instance, there are known transgenic plants with an elevated starch content or altered starch quality, or those with a different fatty acid composition in the harvested material.

Preference is given to the use of the herbicidal compositions in economically important transgenic crops of useful plants and ornamentals, for example of gramineous crops such as wheat, barley, rye, oats, millet/sorghum, rice and corn, or else crops of sugar beet, cotton, soya, oilseed rape, potatoes, tomatoes, peas and other vegetables. The herbicidal compositions can preferably be used in crops of useful plants which are resistant, or have been made resistant by recombinant means, to the phytotoxic effects of the herbicides.

When the herbicidal compositions are employed in transgenic crops, not only do the effects toward harmful plants to be observed in other crops occur, but frequently also effects which are specific to application in the particular transgenic crop, for example an altered or specifically widened spectrum of weeds which can be controlled, altered application rates which can be used for the application, preferably good combinability with the further herbicidally active compounds to which the transgenic crop is resistant, and influencing of growth and yield of the transgenic crop plants.

The present invention thus also provides a method for controlling unwanted plant growth, preferably in crop plants such as cereals (e.g. wheat, barley, rye, oats, rice, corn, millet/sorghum), sugar beet, sugar cane, oilseed rape, cotton and soya, more preferably in monocotyledonous crops such as cereals, for example wheat, barley, rye, oats, crossbreeds thereof, such as triticale, rice, corn and millet/sorghum, which is characterized in that the herbicidal compositions according to the invention are applied to the weeds, plant parts, plant seeds or the area in which the plants grow, for example the area under cultivation. The crop plants may also have been genetically modified or obtained by mutation selection and are preferably tolerant to acetolactate synthase (ALS) inhibitors.

With the WGs and SCs according to the invention, a better biological effect can be achieved at the same application rate. Advantageously, the SCs according to the invention exhibit excellent plant compatibility, such as a reduced tendency to cause phytotoxic damage.

In addition, the SCs according to the invention in the form of specific active compound combination formulations (synonyms: mixture formulations, co-formulations) have further advantages, for example lower expenditure on packaging than in the case of use of the individual active compounds, as a result of which the cost and inconvenience associated with production, transport and storage is reduced and the preparation of the spray liquors used in agriculture is better manageable through the smaller amounts and the effective ratios that have already been set, for example in the measuring and stirring operation.

The SCs according to the invention surprisingly additionally exhibit excellent dispersing and stabilizing properties after further dilution with liquids, preferably water.

In addition, the SCs give rise to formulations which have prolonged storage stability and impeccable applicability.

A further preferred embodiment is the use of the SCs according to the invention as growth regulator (phytotonic). Preferably, these combinations are used to improve the "greening" of the plant.

Plant growth regulators can exert various effects on plants. The effect of the substances depends essentially on the time of application relative to the development stage of the plant, and also on the amounts of active compound that are deployed to the plants or their environment and on the manner of deployment. In each case, growth regulators should exert a particular desired effect on the crop plants.

The growth-regulating effects include earlier germination, better emergence, a more highly developed root system and/or improved root growth, enhanced tillering capacity, more productive tillers, earlier flowers, increased plant height and/or biomass, stem shortening, improvements in shoot growth, number of grains/ears, number of ears/m2 , number of stolons and/or number of flowers, increased harvest index, larger leaves, fewer dead basal leaves, improved phyllotaxy, earlier maturity/earlier fruit formation, homogeneous maturity, increased grain filling time, better fruit formation, larger fruit/vegetable size, shoot resistance and reduced lodging.

Elevated or improved yield relates to total biomass per hectare, yield per hectare, grain/fruit weight, seed size and/or hectolitre weight, and to improved product quality, comprising the following:

improved processibility with regard to size distribution (grain, fruit, etc.), homogeneous maturity, grain moisture, better milling, better wine processing, better brewing, elevated juice yield, elevated harvestability, elevated digestibility, elevated sedimentation value, elevated drop count, elevated husk stability, elevated storage stability, improved fibre length/thickness/homogeneity, elevated milk and/or meat quality of silage fed animals, adaptation to cooking and frying; further comprising better marketability in relation to elevated fruit/grain quality, size distribution (grain, fruit, etc.), elevated storability/shelf life, firmness/softness, flavour (aroma, texture, etc.), class (size, shape, number of berries, etc.), number of berries/fruits per bunch, crispness, freshness, wax coverage, frequency of physiological disorders, colour, etc.; further comprising an increase in the desired constituents, for example protein content, fatty acids, oil content, oil quality, amino acid composition, sugar content, acid content (pH), sugar/acid value (Brix), polyphenols, starch content, nutritional value, gluten content/index, energy content, flavour, etc.; and further comprising a reduction in unwanted constituents, for example fewer mycotoxins, fewer aflatoxins, geosmin content, phenol aromas, laccase, polyphenol oxidases and peroxidases or nitrate content.

Plant growth-regulating formulations may be used, for example, to slow the vegetative growth of the plants. Such suppression of growth is of economic interest for example in the case of grasses, since it is possible in this way to reduce the frequency of grass cutting in ornamental gardens, parks and sports facilities, on road margins, at airports or in fruit crops. Likewise important is the inhibition of growth of herbaceous and woody plants on road margins and close to pipelines or above-ground cables, or generally wherever vigorous plant growth is unwanted.

Likewise important is the use of growth regulators for inhibition of the longitudinal growth of cereals. This reduces or entirely eliminates the risk of lodging of the plants prior to harvesting. In addition, growth regulators can strengthen the stem in cereals, which likewise counteracts lodging. The use of growth regulators for shortening and strengthening the stems permits the deployment of greater amounts of fertilizer, in order to increase the yield, without any risk of lodging of the cereal crop.

In the case of many crop plants, the suppression of vegetative growth permits greater plant density, and it is therefore possible to achieve higher numbers in relation to the soil surface area. A further advantage of the smaller plants obtained in this manner is that the crop is easier to cultivate and to harvest.

The reduction in vegetative plant growth can also lead to elevated or improved yields, since the nutrients and assimilates are of greater benefit for flower and fruit formation than for the vegetative parts of the plants.

Alternatively, growth regulators can also be used to promote vegetative growth. This is of great benefit when harvesting the vegetative plant parts. However, promoting vegetative growth may also promote generative growth in that more assimilates are formed, resulting in more or larger fruits.

Furthermore, beneficial effects on growth or yield can be achieved through improved nutrient use efficiency, especially nitrogen (N) use efficiency, phosphorus (P) use efficiency, water use efficiency, improved transpiration, respiration and/or C02 assimilation rate, better nodulation, improved Ca metabolism etc.

Likewise, growth regulators can be used to alter the composition of the plants, which in turn may result in an improvement in the quality of the harvested product. Under the influence of growth regulators, parthenocarpic fruits may be formed. Moreover, it is possible to influence the gender of the flowers. It is also possible to produce sterile pollen, which is of great importance in the breeding and production of hybrid seeds.

Branching of the plants may be controlled by using growth regulators. On the one hand, breaking apical dominance can promote the development of secondary shoots, which can be very desirable, especially when growing ornamental plants, also in combination with growth inhibition. On the other hand, it is also possible, however, to inhibit the growth of the secondary shoots. This effect is of particular interest, for example, when growing tobacco or when growing tomatoes.

Under the influence of growth regulators, the amount of leaves on the plant can be controlled in such a way that the plants are defoliated at a certain point in time. Such defoliation plays an essential role in the mechanical harvesting of cotton, but is also of interest in facilitating harvesting in other crops, for example in viticulture. The defoliation of the plants can also be carried out in order to reduce the transpiration of the plants before replanting.

Furthermore, growth regulators can modulate plant senescence, which may result in prolonged green leaf area duration, a longer grain filling phase, improved yield quality, etc.

Growth regulators can also be used to regulate fruit dehiscence. On the one hand, it is possible to prevent premature fruit dehiscence. On the other hand, it is also possible to promote fruit dehiscence or even flower shedding to achieve a desired mass ("thinning"). In addition it is possible to use growth regulators at the time of harvest to reduce the force required to detach the fruits, in order to allow mechanical harvesting or to facilitate manual harvesting.

Growth regulators can also be used to achieve a faster or else delayed ripening of the crop before or after the harvest. This is particularly advantageous as it allows an optimal adjustment to the requirements of the market. Moreover, growth regulators in some cases can improve the fruit colour. In addition, growth regulators can also be used to synchronize maturation within a certain period of time. This is the prerequisite for complete mechanical harvesting or manual harvesting in a single operation, for example with tobacco, tomatoes or coffee.

Through the use of growth regulators, it is additionally possible to influence dormany of the plants' seeds or buds in such a way that plants such as pineapples or ornamental plants in garden centres, for example, germinate, sprout or bloom at a time when they would not normally tend to do so. Where there is a risk of frost, it may be desirable to delay budding or the germination of seeds with growth regulators in order to avoid damage by late frost.

Finally, growth regulators can induce plant resistance to frost, drought or high salinity of the soil. This allows plants to be grown in regions that are normally not suitable for this purpose.

The formulations according to the invention also exhibit a potent strengthening effect in plants. Accordingly, they can be used for mobilizing the defences of the plant against attack by undesirable microorganisms. Plant-strengthening (resistance-inducing) substances in the present context are substances capable of stimulating the defence system of plants in such a way that the treated plants, when subsequently inoculated with undesirable microorganisms, develop a high degree of resistance to these microorganisms.

Further, plant physiological effects in the context of the present invention comprise the following:

abiotic stress tolerance, comprising tolerance to high or low temperatures, drought tolerance and recovery after drought stress, water use efficiency (correlating to reduced water consumption), flood tolerance, ozone stress and UV tolerance, tolerance towards chemicals like heavy metals, salts, pesticides etc.

Biotic stress tolerance, comprising increased fungal resistance and increased resistance against nematodes, viruses and bacteria. In the context of the present invention, biotic stress tolerance preferably comprises increased fungal resistance and increased resistance against nematodes.

Increased plant vigour, comprising plant health/plant quality and seed vigour, reduced stand failure, improved appearance, increased recovery after periods of stress, improved pigmentation (e.g. chlorophyll content, stay-green effects, etc.) and improved photosynthetic efficiency.

The present invention accordingly provides for the use of the SCs according to the invention for enhancing the resistance of plants to abiotic stress factors, preferably to drought stress, in particular for strengthening plant growth and/or for increasing plant yield.

The further various benefits for plants mentioned above can be combined in a known manner in component form, and generally applicable terms can be used to describe them. Such terms are, for example, the following names: phytotonic effect, resistance to stress factors, less plant stress, plant health, healthy plants, plant fitness, plant wellness, plant concept, vigour effect, stress shield, protective shield, crop health, crop health properties, crop health products, crop health management, crop health therapy, plant health, plant health properties, plant health products, plant health management, plant health therapy, greening effect or regreening effect, freshness, or other terms with which a person skilled in the art is entirely familiar.

In the text which follows, SCs according to the invention are referred to collectively as formulations according to the invention.

The invention is illustrated in more detail by the examples below, without being limited thereby.

Examples

Substances and abbreviations used:

The terms used in the examples below have the following meanings:

mefenpyr-diethyl diethyl (RS)-1-(2,4-dichlorophenyl)-5-methyl-2-pyrazoline-3,5-dicarboxylate, (Bayer CropScience AG), melting range 50-55°C

flufenacet 4'-fluoro-N-isopropyl-2-(5-trifluoromethyl-1,3,4-thiadiazol-2-yloxy)acetanilide (Bayer CropScience AG)

diflufenican 2',4'-difluoro-2-(a,a,a-trifluoro-m-tolyloxy)nicotinanilide (Bayer CropScience AG)

DCPMI 2-[(2,4-dichlorophenyl)methyl]-4,4'-dimethyl-3-isoxazolidinone (CAS Number 81777-95-9 or IPUAC 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, abbreviated hereinafter to DCPMI)

Morwet D-425 naphthalenesulfonic acid/formaldehyde condensate, sodium salt (Akzo Nobel)

Pluronic© PE 10500 propylene oxide-ethylene oxide (PO-EO) block polymer (BASF)

citric acid polybasic organic acid

Rhodopol* G xanthan derivative (Solvay)

Silcolapse* 426R, 411 silicone defoamer (Solvay)

Sipernat 50S finely divided silica, Evonik, BET surface according to ISO 9277: 400-600 m^2/g

glycerol antifreeze

Proxel®GXL preservative (biocide, Proxel)

Production example

Production of a suspension concentrate (SC):

First of all, water is initially charged at room temperature. Components a), b), c), d) and g) and also e) are then added with stirring. In the case of e)= mefenpyr-diethyl, the component is added warm at 65°C and the mixture is stirred for 2 to 24 h until crystals form. This is followed by wet grinding, for example by means of a bead mill. Finally, the organic thickener (component f) is added.

Table 1: Formulations produced (figures are in per cent by weight, % by weight) Component Example

2 3 4 5 1

(according (according (according (comparati (comparativ to the to the to the ye) e) invention) invention) invention)

mefenpyr diethyl

a DCPMI 40 20 20 20 9

d diflufenican 4.5

d flufenacet 9

Morwet* D b1 1.0 1.0 1.0 1.0 1.0 425

Pluronic*PE b2 5 5 5 5 5 10500

g citric acid 0.1 0.1 0.1 0.1 0.1

c Sipernat 50S 1 1 8 5 3

f Rhodopol*23 0.2 0.2 0.1 0.1 0.1

g Silcolapse* 411 0.5 0.5 0.5 0.5 0.5

g glycerol 5 5 5 5 5

g Proxel* GXL 0.18 0.18 0.18 0.18 0.18

water ad 100 ad 100 ad 100 ad 100 ad 100

DCPMI:Sipernat 40 20 2.5 4 3 ratio

Total: 100 100 100 100 100

Comparative example 3 was prepared analogously to example 5 from PCT/EP2017/069701 as a capsule suspension.

Determination of the relative volatility and cuticle penetration of the active compound

A spray liquor (0.5 g of active compound/l) is placed onto three Teflon membranes in each case in a glass box open at the top in a laboratory fume hood under a constant air flow of 1.6 m/s at 22°C and 60% relative air humidity. The residue on the Teflon membranes is determined by HPLC after drying after 0 and 24 h. The volatility is based on the 0 h value. The bioavailability is determined using apple cuticle penetration. A spray liquor (0.5 g of active compound/l) is placed on three apple cuticles in each case. The amount of active compound in the cuticle is measured; determined by HPLC after drying after 0 and 24 h.

100% relative volatility means that no active compound has been lost through volatility. 100% cuticle penetration means that the active compound has completely penetrated into the plant. High penetration (= bioavailability of the active compound in the plant) and low volatility are desirable. Ideally, therefore, both values are at 100%. However, a 100% reduction in volatility is not necessary if the active compound penetrates into the plant quickly enough. The higher the penetration into the plant, the less active compound is generally available for volatilization.

Table 2: Determination of volatility and cuticle penetration

Relative Cuticle Example volatility penetration mm % after in % after 24 h 24 h

Comparison 1 5 40

Comparison 2 7 38 Comparison 3 (example 5 from 100 10 PCT/EP2017/069701) According to the 65 85 invention 3 According to the 35 70 invention 4 According to the 50 70 invention 5

Comparative example 1 shows that too low a ratio of active compound to Sipernat is not sufficient to reduce the volatility. Comparative example 2 shows that capsules are able to reduce the volatility by 100%, but the active compound is hardly bioavailable (10% cuticle penetration).

The examples according to the invention not only show a reduction in volatility (35-65%) but also show an increase in cuticle penetration. Thus, the active compound is less volatile and at the same time more bioavailable.

Greenhouse

In order to confirm the results from the cuticle penetration and volatility from the laboratory, greenhouse experiments were carried out. The aim was not only to check the results under real conditions, but also to additionally differentiate efficiency (weed control of the grass ALOMY = Alopecurus myosuroides = slender meadow foxtail) and phytoxicity (damage to the crop, winter wheat). In a greenhouse in a 4 * 4 *m^ 3 area protected with PE film, a 1% spray liquor was applied in water to winter wheat. Stellaria media plants were placed 1 m away from the wheat. The respective soil was provided with typical weeds. Phytotoxic damage to winter wheat and the degree of weed control were measured. The volatility was assessed by damage to Stellaria media (STEME).

Example Damage to STEME Phytotoxicity Efficiency against ALOMY

Comparison 1 (SC) 60 18 55

Comparison 3 (CS) 5 0 20 (example 5 from PCT/EP2017/069701)

Example 3 (according to 8 0 64 the invention)

Example 4 (according to 30 8 93 the invention)

The formulations according to the invention with the herbicidally active compounds show an improved reduction in damage to neighbouring crops, with a higher activity and reduced phytotoxicity.

Claims (15)

Claims

1. An aqueous suspension concentrate, containing a) 2-[(2,4-dichlorophenyl)methyl-4,4'-dimethyl]-3-isoxazolidinone, b) at least one dispersant, c) carrier material, d) optionally at least one agrochemical active compound different from a), e) optionally at least one safener, f) optionally at least one thickener, and g) optionally further additives and auxiliaries.

2. The suspension concentrate as claimed in claim 1, characterized in that the proportion of component a) is 0.5 to 35% by weight b) is 1.0 to 15% by weight, c) is 0.1 to 10% by weight d) is 0% e) is 1-15 %by weight, f) is 0.01 to 1.00% by weight, and g) is 0 to 20% by weight, with water being added to 100% by weight.

3. The suspension concentrate as claimed in claim 1, characterized in that the proportion of component a) is 5 to 30% by weight b) is 2.0 to 10% by weight, c) is 0.3 to 8.0% by weight d) optionally at least one agrochemical active compound different from a), e) is 2.0 to 12.0% by weight, f) is 0.01 to 0.60% by weight, and g) is 3.0 to 10.0% by weight, with water being added to 100% by weight.

4. The suspension concentrate as claimed in claim 1, characterized in that the proportion of component a) is 10 to 30% by weight b) is 2.50 to 8.0% by weight, c) is 1.0 to 7.0% by weight d) optionally at least one agrochemical active compound different from a), e) is 3.0 to 8.0% by weight, f) is 0.04 to 0.50% by weight, and g) is 5.0 to 10.0% by weight, with water being added to 100% by weight.

5. The suspension concentrate as claimed in claim 1, characterized in that the proportion of component a) is 15 to 25% by weight b) is 2.5.0 to 8.0% by weight, c) is 1.0 to 7.0% by weight d) optionally at least one agrochemical active compound different from a), e) is 3.0 to 8.0% by weight, f) is 0.05 to 0.30% by weight, and g) is 5.0 to 10.0% by weight, with water being added to 100% by weight.

6. The suspension concentrate as claimed in any of claims 1-5, characterized in that a further active compounds d) is present, the total proportion of components a) and d) being 0.5 to 35% by weight, preferably 5 to 30% by weight, particularly preferably 10 to 30% by weight and very particularly preferably 15 to 25% by weight, where the proportion of component a) is reduced by component d).

7. The suspension concentrate as claimed in any of claims 1-5, characterized in that b) is a mixture of bl) and b2, the proportion of the anionic dispersant bl) in the suspension concentrates as claimed in the invention being 0.1 to 10% by weight, preferably 0.2 to 7% by weight and very particularly preferably 0.3 to 4% by weight, and the proportion of the non-ionic dispersant b2) in the suspension concentrates as claimed in the invention being 1 to 15% by weight, preferably 2 to 10% by weight and very particularly preferably 2.5 to 8% by weight, where the total proportion is not exceeded by the sum of bl) and b2).

8. The suspension concentrate as claimed in claim 6, characterized in that the proportion of bl) is 0.3 to 1.5% by weight and the proportion of b2) is 2.5 to 7.5% by weight.

9. The suspension concentrate as claimed in any of the preceding claims, characterized in that the ratio of a) to c) is from1 to 10, more preferably from 2 to 8, particularly preferably 3-6, and most preferably 4.

10. The suspension concentrate as claimed in any of the preceding claims, characterized in that diflufenican and/or flufenacet are present as further active compounds d).

11. The suspension concentrate as claimed in any ofthe preceding claims, characterized in that component

bI) is a 1,2-dibutyl- or 1,2-diisobutylnaphthalenesulfonate,

b2) is a non-ionic dispersant of the polyvinylpyrrolidone type or a block copolymer based on ethylene and propylene oxide, c) is a synthetic fused silica or pyrogenic silica, d) is optionally flufenacet and/or diflufenican, e) is mefenpyr-diethyl, and f) is a thickener based on xanthan.

12. The use of the suspension concentrates as claimed in any of the preceding claims as a herbicide in cereals and oilseed rape, and in this context by the pre-emergence and post-emergence methods.

13. A method for controlling unwanted plants in plant crops, characterized in that the suspension concentrates as claimed in any of claims 1 to 10 are applied to the plants, or the area on which the plants grow.

14. The use of the suspension concentrates as claimed in any of claims 1 to 10 for controlling harmful plants in transgenic crop plants.

15. The use of the suspension concentrates as claimed in any of claims I to 10 for treating plants where the seed has been treated with safener.