EP2166861A2 - Use of fungicides for making the phenological development of oil plants more coherent - Google Patents

Abstract

The invention relates to the use of certain fungicides for achieving a more homogeneously timed development of oil plants. The invention also relates to a method for increasing the quality and optionally the quantity of oil plant products.

Description

 Use of fungicides for the greater standardization of the phenological development of oil plants

The present invention relates to the use of certain fungicides to achieve a more timely sequence of development of oil plants. It also relates to a method for increasing the quality and, where appropriate, the quantity of oil plant products.

The development within a plant is usually not uniform and homogeneous. Thus, the different "floors" of the plant (ie the different, especially the upper, middle and lower or the outer and inner areas of the plant) may flower at different times and thus form at different times ripe fruits / seeds For many agriculturally important plants, it is generally neither economically viable nor harvestable to harvest multiple times depending on the maturity of the individual plant stages However, fruits which are either still immature or already overripe at this time may often not be utilized, or at least not maximally utilized in terms of quantity and / or quality, thus significantly reducing the actual yield and / or quality of the crop it depends on what the plant carries t, could be.

For further utilization, e.g. for oil production, oleaginous plants often use oil-containing fruits / seeds which do not have the optimal degree of ripeness, i. overripe or immature. However, this has the consequence that the quality of the plant products, e.g. of the oil or its reaction products, can be adversely affected. However, a high quality of such oil plant products is not only of great importance in the food and cosmetics sector; Even when used as regenerative fuels, high quality standards must be met.

Due to the foreseeable depletion of fossil fuels, the energy sector is increasingly focusing on renewable fuels, such as vegetable oils, biodiesel and bioethanol. Biodiesel refers to the lower alkyl esters, in particular the methyl esters, of fatty acids. These are obtainable by transesterifying vegetable oils, such as rapeseed oil, but also used fats and used oils and animal fats, which occur in nature as triglycerides, with an alcohol, such as methanol. Vegetable oils are usually obtained by pressing the oil-containing plant parts of oil plants, for example of oily fruits or seeds. However, in the cold-pressing process, and especially in the hot pressing process, an oil is obtained which has a relatively high content of phosphorus compounds and mineral compounds, such as alkali and in particular alkaline earth metal compounds, especially calcium and magnesium compounds. These compounds, which may be present not only in the oil but also in reaction products thereof, may have a negative impact on combustion in engines and combustion plants. In addition, they have a negative effect on the material resistance of engines. Negative effects on the exhaust systems are also possible. Thus, the compounds mentioned in the combustion process lead to a considerable ash formation, which loads, for example, particulate filter of diesel vehicles. The ash can not be removed by regeneration of the particulate filter, but is held in the filter, which leads to an increase in the exhaust backpressure. An increased exhaust back pressure in turn leads to malfunctions in the diesel engine. Phosphorus compounds also act as catalyst poisons and reduce, for example, the life of oxidation catalysts in diesel vehicles and of SCR catalysts in commercial vehicles, such as trucks and tractors. Even in heating systems, similar problems can occur. To avoid these problems and to be able to meet the expected in the near future DIN standard for rapeseed oil as a fuel (E DIN 51605), currently biodiesel or the underlying vegetable oils are subjected to elaborate work-up procedures.

Even if the above-mentioned DIN standard for rapeseed oil is observed, there is no guarantee that problems will arise during the transport, storage or combustion of vegetable oils or their reaction products. Thus, certain phosphorus compounds, in particular phospholipids, even if they are contained in an amount below the prescribed by the DIN 51605 phosphorus limit in vegetable oil, lead to a sticking of fuel filters in engines, tanks and industrial production equipment. It is therefore desirable to lower the phosphorus content and also the content of other undesirable accompanying substances in the oil even more than specified by DIN 51605.

Also in the use of vegetable oils in the food and cosmetics sectors or of oil plant products, e.g. of seeds and press cakes, in the feed sector, phosphorus compounds, in particular phosphates, e.g. be problematic for health reasons.

Since basically all plant parts, such as press cake and seeds, can be used as regenerative fuels, it is also important for these oil plant products to have the lowest possible phosphorus and mineral content. Another problem of oil plant products and in particular of vegetable oils and possibly also of reaction products thereof is their acidity, which can lead to corrosion in engines and furnaces, eg in boilers.

It is also desirable to provide vegetable oils and reaction products thereof with the lowest possible iodine number. The iodine value is a measure of the number of C-C double bonds in the fatty acid molecules on which the oil or its reaction products are based, i. for the unsaturated character of the oil. High iodine oils are more susceptible to oxidation and thus resinify faster than oils with a higher degree of saturation, so that their storage stability is lower. Overall, the provision of vegetable oils or reaction products thereof with the highest possible oxidation stability is desirable because sufficient oxidative stability, which is an important aspect of storage stability, is essential for successful commercialization. The oxidation stability is determined not only by the degree of saturation of the oil, but also by the presence of antioxidants, such as vitamin A or vitamin E.

Another problem of vegetable oils, especially in terms of their use in the fuel field, is their relatively high viscosity compared to mineral fuels. High viscosities lead due to the poorer flow, pumping and Zerstäubungsverhaltens at the injection nozzles (droplet spectrum and geometry of the injection jet), among other things to cold start problems. It is therefore desirable to be able to provide vegetable oils of reduced viscosity, in particular of reduced kinematic viscosity.

Further improvements in the properties of oil crop products, particularly vegetable oils and their reaction products, in terms of their utilization for energy production is desirable, for example a higher flash point, a higher calorific value, a higher cetane number, a lower coke residue, a reduced sulfur content, a reduced one Nitrogen content, a reduced chlorine content and a lower content of certain (semi) metal compounds, such as zinc, tin, boron and silicon compounds of oil plant products, especially of vegetable oil or reaction products.

The flash point refers to the measured temperature at which vapors evolve in a closed vessel, resulting in a spark-in-air mixture that can be ignited by spark ignition. The flash point is used to classify liquids in hazard classes. Of course, it is desirable worth to provide vegetable oils and reaction products thereof with the highest possible flashpoint.

The calorific value is a measure of the amount of energy released by the complete combustion of a substance per volume or mass. The upper calorific value (also referred to as the calorific value) also contains the energy released during the condensation of the water vapor produced during combustion, while the lower net calorific value is adjusted. It goes without saying that oil product products with the highest possible lower calorific value are desirable.

The cetane number is a measure of the ignitability of a diesel fuel and, of course, ignition-willing fuels are particularly desirable.

The coke residue is composed of organic and inorganic material that results from incomplete combustion of fuel and is a measure of the coking tendency of a fuel at the injection nozzles and for residue formation in the combustion chamber. The coking of injectors leads to a poorer distribution of the injected fuel and thus to a reduction in engine performance. The coking is currently suppressed in engines, especially by adding special detergents and dispersants. Fuels that have a lower tendency to coke are of course desirable.

The reduction of the contents of sulfur, nitrogen, chlorine and said (semi) metals is intended above all to reduce the emission of harmful substances harmful to the health, such as sulfuric acid and other sulfur compounds and nitrous gases, to reduce the corrosive action of oil plant products all of vegetable oils and reaction products thereof, metal parts coming into contact with them and the reduction of ash formation, eg by the said (semi) metal compounds serve.

The above-mentioned quality criteria are influenced, among other things, by the degree of ripeness of the oil plant or its fruit / seed.

As stated earlier, multiple harvests in the course of ripening of the plant to ensure that the plant products have a high quality in terms of the above criteria, but not economical, usually technically difficult to implement and therefore also no usual practice; ie it is regularly harvested only once. The object of the present invention was therefore to provide compounds which cause the individual development phases within plants, in particular of oil plants, to become more homogeneous in themselves and thus within shorter time intervals. In particular, the maturation of the fruit / seeds should be as homogeneous as possible, ie within a shortened time interval.

Surprisingly, it has been found that a more homogeneous development of the plant is obtained by treating the oil crops or their seed with certain fungicides.

The object has accordingly been achieved by the use of at least one fungicide which is selected from aryl and heterocyclylamides, carbamates, dicarboximides, azoles, strobilurins and morpholines, optionally in combination with at least one growth regulator, in order to achieve a temporally more uniform course of the development of oil plants.

The more consistent timing of the development of the oil crops relates to a standardization compared to the development of the same oil crop (in terms of species and variety) under the same growth conditions of the plant, but without the treatment of the plant or its seed with the specified fungicides.

"Temporally more consistent development of oil plants" means that individual growth stages of the plants take place in a narrower time window, in particular the growth in length, the shooting and in particular the flowering and / or the ripening of the fruits / seeds.

Preferably, by the use of the specified fungicides according to the invention, the growth in length and / or the shoot and / or the flowering within the plant and / or the ripening of the fruit / seed of the plant are carried out in a more uniform, i. within a narrower time interval compared to plants not treated according to the invention.

Particularly preferably, the flowering takes place within the plant and / or the ripening of the fruit / seed of the plant in a more uniform, ie within a narrower time interval in comparison to plants not treated according to the invention. In particular, the ripening of the fruit / seed of the plant takes place in a more uniform time frame, ie within a narrower time interval in comparison to plants not treated according to the invention. "Within the plant" means that the development in one and the same plant is more concentrated.

Oil plants are plants from whose parts of plants, in particular their fruits and / or seeds, oil is obtained. They can be divided into two main groups:

Pulp oil plants in which the oil is obtained from the fatty pulp. These include, for example, the olive tree and the oil palm.

Seed oil plants in which the oil is extracted from the seeds. These include, for example, rape, turnip rape, mustard, oil radish, camelina, Ölrauke, Krambe, sunflower, safflower, thistle, marigold, soybean, lupine, flax, hemp, pumpkin, poppy, corn and nuts, especially arachides (peanuts).

To the seed oil plants one can count in principle also the two kinds mentioned above with the Fruchtfleischölpflanzen (olive tree and oil palm), because from both also the seed (core) is used for the oil production.

Preferred oil plants are seed oil plants in the strict sense, i. Oil plants that have no additional oily pulp.

In the context of the present invention, the terms "fruit" and "seed" which underlie the definition of the terms "pulp oil plants" and "seed oil plants" are not strictly morphologically used, ie it is not distinguished according to which parts of the flower seed or the fruit has arisen. Rather, in the context of the present invention, the term "seed" is understood as meaning that part of the plant which can be used as such, ie without further treatment, as seed.The fruit, on the other hand, is the totality of the organs which emerge from a flower, that is the seeds A fruit comprises one or more seeds surrounded by a pericarp pericarp For the purposes of the present invention, a fruit also comprises pulp which is easily separated from the seed in a morphological sense For the purposes of the invention, seed oil plants thus encompass both oil plants in which the oil is obtained from seeds in a morphological sense, and oil plants in which the oil originates from the seed such fruit is obtained in which the pericarp is inseparable from the seed, as be Ispielsweise with sunflowers, nuts or corn is the case. Accordingly is in the context of the present invention, the term "seed coat" is not limited to the shell of seeds in a morphological sense, but also includes the fruit peel (fruit wall) of fruits in which the pericarp is inseparable from the seed and thus under the term used in the invention "Seeds" fall.

Preferably, however, the term "fruits / seeds" is understood to mean the seeds without separable pulp.

Furthermore, the invention relates to a method for increasing the quality and, where appropriate, the quantity of oil plant products, comprising a (live) oil plant or (living) plant parts thereof or their seeds (ie the seed from which the plant grows) with at least one fungicide optionally in combination with at least one growth regulator, as defined above, harvesting the fruit / seeds of the oil plant when their water content is at most 15% by weight based on the total weight of the fruits / seeds and the oil plant product wins, the increase in quality being selected according to the following criteria: (i) reducing the phosphorus content of at least one oil crop product; (ii) reducing the alkali and / or alkaline earth content of at least one oil plant product;

(iii) increasing the oxidation stability of at least one oil plant product; (iv) reducing the overall pollution of at least one oilseed product; (v) lowering the iodine value of at least one oil plant product; (vi) lowering the acid number of at least one oil plant product; (vii) reducing the kinematic viscosity of at least one oil crop product; (viii) reducing the sulfur content of at least one oil crop product; (ix) increasing the flashpoint of at least one oil plant product;

(x) increasing the net calorific value of at least one oilseed product; (xi) reducing the coke residue of at least one oil crop product; (xii) increasing the cetane number of at least one oil plant product; (xiii) reducing the nitrogen content of at least one oil crop product; (xiv) reducing the chlorine content of at least one oilseed product; and (xv) reducing the content of tin, zinc, silicon and / or boron of at least one oil crop product. However, those criteria which are not improved by individual treatments according to the invention are preferably not worsened either.

The increased quality and optionally increased quantity of the at least one oilseed product relates to an improvement compared to the quality and possibly quantity of the same oil plant product obtained from the same oil plant (in species and variety) under the same growth conditions of the plant but without the treatment of the plant or its seed with the specified fungicides and / or without harvest at the time described, in the same way (in terms of harvesting, processing, etc.) is obtained.

In the context of the present invention, oil plant products are understood as meaning all oil-containing plant parts of oil plants, their processing products and reaction products, as well as the reaction products of the processed products. These are for energy, e.g. in the form of fuels and fuels, as lubricants, but also for use in the food and feed sector or in the cosmetics sector. Olive oil products include, in particular, the oil-containing fruits and seeds of oil plants, the oil obtained therefrom (used in the food industry, eg as edible oil or for the production of margarine, in the cosmetics sector, eg as a carrier, as a lubricant or as fuel and fuel can be), the resulting in oil extraction in the pressing process resulting press cake (which can be used in the feed sector as animal feed or fuel) and the reaction products of the oil, eg its transesterification products with C1-C4 alcohols, preferably with methanol (which can be used as biodiesel). Transesterification products of the oil with C 1 -C 4 -alcohols are understood to mean the C 1 -C 4 -alkyl esters of the fatty acids present in the oil principally as glycerides (more particularly as triglycerides).

Preferably, the oil plant products are vegetable oils and their reaction products, e.g. the transesterification products with Ci-C4-alcohols, preferably with methanol selected.

Oils are understood in the context of the present invention, unless otherwise defined, vegetable oils.

In the context of the present invention, the generic terms have the following meanings: Halogen is fluorine, chlorine, bromine or iodine and in particular fluorine, chlorine or bromine.

The term "partially or fully halogenated" means that one or more, eg, 1, 2, 3, or 4 or all of the hydrogen atoms of a given group are replaced by halogen atoms, especially fluorine or chlorine.

The term "C _m -C _n -alkyl" (also in C _m -C _n -haloalkyl, C _m -C _n -alkylthio, C _m -C _n -haloalkylthio, C 1 -C _n -alkylsulfinyl and C _m -C _n - Alkylsulfonyl) stands for a linear or branched saturated hydrocarbon radical with m to n, eg 1 to 8, carbon atoms.For example, Ci-C4-alkyl is methyl, ethyl, propyl, isopropyl, n-butyl, sec-butyl, Isobutyl or tert-butyl, C 1 -C 8 -alkyl furthermore represents, for example, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2,2-

Dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, heptyl, octyl, 2-ethylhexyl and constitutional isomers thereof.

C 1 -C 5 -haloalkyl (or C _m -C _n -haloalkyl) is a linear or branched alkyl radical having m to n carbon atoms, in which 1 or more hydrogen atoms are replaced by halogen atoms, in particular fluorine or chlorine. Thus, Ci-Cs-haloalkyl is a linear or branched C 1 -C -alkyl radical in which 1 or more hydrogen atoms are replaced by halogen atoms, in particular fluorine or chlorine. In particular, d-Cs-haloalkyl is C 1 -C 2 -haloalkyl. C 1 -C 2 -haloalkyl is, for example, chloromethyl, dichloromethyl, trichloromethyl, bromomethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 2-chloroethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2- Difluoroethyl, 2,2,2-trifluoroethyl, pentafluoroethyl and the like.

Cm-C _n -Al koxy represents a linear or branched alkyl radical having m to n carbon atoms, which is bonded via an oxygen atom. Accordingly, C _T C ₄ - alkoxy is a Ci-C4-alkyl radical which is bonded via an oxygen atom. Examples of these are methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, isobutoxy and tert-butoxy. Examples of C 1 -C 8 -alkoxy are furthermore pentyloxy, hexyloxy, octyloxy and their constitutional isomers.

d-Cs-Haloalkoxy represents a linear or branched C 1 -C 8 -alkyl radical which is bonded via an oxygen atom and in which one or more hydrogen atoms are replaced by a halogen atom, in particular by fluorine or chlorine. Examples these are chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, bromomethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-fluoroethoxy, 2, 2-difluoroethoxy, 2-chloro-2-fluoroethoxy, 2,2-dichloroethoxy, 2,2,2-trichloroethoxy, 2,2,2-trifluoroethoxy, pentafluoroethoxy, pentachloroethoxy and the like.

Ci-Cs-Al kylthio, Ci-Cs-alkylsulfinyl and d-Cs-alkylsulfonyl are a linear or branched Ci-Cs-alkyl radical via a sulfur atom (alkylthio), an S (O) - group (alkylsulfinyl) or S (O) 2-group (alkylsulfonyl) is bonded. Examples of C 1 -C 6 -alkylthio include methylthio, ethylthio, propylthio, isopropylthio, n-butylthio and the like. Examples of C 1 -C 8 -alkylsulfinyl include methylsulfinyl, ethylsulfinyl, propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl and the like. Examples of C 1 -C 8 alkylsulfonyl include methylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl and the like.

C 1 -C 4 -alkylthio is a linear or branched C 1 -C 4 -alkyl radical which is bonded via a sulfur atom. Examples thereof include methylthio, ethylthio, propylthio, isopropylthio, n-butylthio and constitutional isomers thereof.

Ci-Cs-haloalkylthio represents a linear or branched Ci-Cs-alkyl radical which is bonded via a sulfur atom and in which one or more hydrogen atoms are replaced by a halogen atom, in particular by fluorine or chlorine. Examples of these are chloromethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, bromomethylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1-chloroethylthio, 1-bromoethylthio, 1-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-fluoroethylthio, 2 , 2-difluoroethylthio, 2-chloro-2-fluoroethylthio, 2,2-dichloroethylthio, 2,2,2-trichloroethylthio, 2,2,2-trifluoroethylthio, pentafluoroethylthio, pentachloroethylthio and the like.

Cm-C _n -Al koxy-Cm-Cn-a I kyl is a C _m -C _n -alkyl group in which a hydrogen atom is replaced by a C _m -C _n alkoxy group. Accordingly, Ci-Cs-alkoxy-Ci-Cs-alkyl is a Ci-Cs-alkyl group in which a hydrogen atom is replaced by a Ci-Cs- alkoxy group. Examples of these are methoxymethyl, ethoxymethyl, propoxymethyl, methoxyethyl, ethoxyethyl, propoxyethyl, methoxypropyl, ethoxypropyl, propoxypropyl and the like.

Cm-Cn-alkylthio-C-Cn-alkyl is a C _m -C _n -alkyl group in which a hydrogen atom is replaced by a C _m -C _n -alkylthio group. Accordingly, Ci-Cs-Al Cylthio-Ci-Cβ-alkyl for a d-Cs-alkyl group in which a hydrogen atom is replaced by a Ci-Cs-alkylthio group. Examples of these are methylthiomethyl, ethylthio methyl, propylthiomethyl, methylthioethyl, ethylthioethyl, propylthioethyl, methylthiopropyl, ethylthiopropyl, propylthiopropyl and the like.

Cm-Cn-haloalkylthio-C-Cn-alkyl is a C _m -C _n -alkyl group in which a hydrogen atom is replaced by a C _m -C _n haloalkylthio group. Accordingly, C 1 -C 6 haloalkylthio-C 1 -C 8 -alkyl represents a C 1 -C 5 -alkyl group in which one hydrogen atom has been replaced by a C 1 -C 6 -haloalkylthio group. Examples of these are chloromethylthio methyl, dichloromethylthiomethyl, trichloromethylthiomethyl, chloroethylthiomethyl, dichloroethylthiomethyl, trichloroethylthiomethyl, tetrachloroethylthiomethyl, pentachloroethylthiomethyl and the like.

Carboxy is a group -COOH.

C-i-Cβ-alkylcarbonyl represents a group -CO-R, wherein R is d-Cs-alkyl.

Ci-Cs-Alkyloxycarbonyl (also called d-Cs-alkoxycarbonyl) is a group -C (O) OR, wherein R is Ci-C ₈ -alkyl.

Ci-Cs-Alkylcarbonyloxy represents a group -OC (O) -R, wherein R is d-Cs-alkyl.

d-Cs-Alkylaminocarbonyl represents a group -CO-NH-R, wherein R is d-Cs-alkyl.

Di- (C 1 -C 8 -alkyl) -aminocarbonyl represents a group -CO-N (RR ') in which R and R' independently of one another represent d-Cs-alkyl.

C2-C8 alkenyl is a linear or branched hydrocarbon radical having 2 to 8 carbon atoms and a double bond in any position. Examples of these are ethenyl, 1-propenyl, 2-propenyl (AIIyI), 1-methylethenyl, 1-, 2- and 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1, 2 , 3- and 4-pentenyl, 1-, 2-, 3-, 4- and 5- hexenyl, 1-, 2-, 3-, 4-, 5- and 6-hepetenyl, 1-, 2-, 3-, 4-, 5-, 6- and 7-octenyl and constitutional isomers thereof.

C2-C8 alkenyloxy represents a C2-C8 alkenyl radical which is bonded via an oxygen atom. Examples of these are ethenyloxy, propenyloxy and the like. C2-C8 alkenylthio represents a C2-C8 alkenyl radical which is bonded via a sulfur atom. Examples of these are ethenylthio, propenylthio and the like.

C2-C8 alkenylamino represents a group -NH-R, wherein R is C2-Cs-alkenyl.

N, -Cs-alkenyl-Nd-Cs-alkylamino represents a group -N (RR '), wherein R is C 2 -C ₈ -alkenyl and R' is C 1 -C ₈ -alkyl.

C 2 -C 8 -alkynyl is a straight-chain or branched hydrocarbon radical having 2 to 8 carbon atoms and at least one triple bond. Examples of these are ethynyl, propynyl, 1- and 2-butynyl and the like.

C2-C8-alkynyloxy is a C2-C8-alkynyl radical which is bonded via an oxygen atom. Examples of these are propinyloxy, butynyloxy and the like.

C 2 -C 8 -alkynylthio is a C 2 -C 8 -alkynyl radical which is bonded via a sulfur atom. Examples of these are ethynylthio, propynylthio and the like.

C2-Cs-Alkynylamino represents a group -NH-R, wherein R is C2-Cs-alkynyl.

N ^ -Cs-alkynyl-Nd-Cs-alkylamino represents a group -N (RR ') in which R is C 2 -C ₈ -alkynyl and R' is C 1 -C ₈ -alkyl.

C3-C8-Cycloalkyl represents a monocyclic 3- to 8-membered saturated cycloaliphatic radical. Examples of these are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl. C3-Cio-Cycloalkyl is a monocyclic 3- to 10-membered saturated cycloaliphatic radical. Examples of these are in addition to the radicals mentioned for Cs-Cs-cycloalkyl cyclononyl and cyclodecyl.

Cs-Cs-Cycloalkyloxy (or Cs-Cs-cycloalkoxy) represents an oxygen-bonded Cs-Cs-cycloalkyl radical. Examples of these are cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cycloheptyloxy and cyclooctyloxy.

Cs-Cs-Cycloalkylthio is a C3-C8-cycloalkyl radical bonded via a sulfur atom. Examples of these are cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cycloheptylthio and cyclooctylthio.

C3-C8-Cycloalkylamino represents a group -NH-R, wherein R is Cs-Cs-cycloalkyl. N -C 3 -C ₈ -cycloalkyl-N-C 1 -C ₈ -alkylamino represents a group -N (RR ') in which R is C 3 -C ₈ -cycloalkyl and R' is C 1 -C ₈ -alkyl.

Cs-Cs-Cycloalkenyl is a monocyclic 3- to 8-membered unsaturated cycloaliphatic radical having at least one double bond. Examples of these are cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclopentadienyl, cyclohexyl, cyclohexyladienyl, cycloheptenyl, cycloheptadienyl, cyclooctyl, cyclooctadienyl, cyclooctatranyl and cyclooctatetraenyl.

Cs-Cs-Cycloalkenyloxy represents an oxygen-bonded C3-C8-

Cycloalkenyl. Examples thereof are cyclopropenyloxy, cyclobutenyloxy, cyclopentenyloxy, cyclopentadienyloxy, cyclohexenyloxy, cyclohexadienyloxy, cycloheptenyloxy, cycloheptadienyloxy, cyclooctenyloxy, cyclooctadienyloxy, cyclooctatrienyloxy and cyclooctatetraenyloxy.

Cm-Cn-alkylene is a linear or branched alkylene group with m to n, z. B. 1 to 8, carbon atoms. Thus, C 1 -C 3 -alkylene is, for example, methylene, 1, 1 or 1, 2-ethylene, 1, 1, 1, 2, 2,2 or 1, 3-propylene. C ₂ -C ₄ -alkylene, for example, represents 1, 1 or 1, 2-ethylene, 1, 1, 1, 2, 2,2 or 1, 3-propylene, 1, 1, 1, 2 -, 1, 3 or 1, 4-butylene. C ₃ -C ₅ -alkylene is, for example, 1, 1, 2, 2, 2 or 1, 3-propylene, 1, 1, 1, 2, 1, 3 or 1, 4 Butylene, 1, 1-dimethyl-1,2-ethylene, 2,2-dimethyl-1,2-ethylene, 1,1,1,1,2,1,3,4,1 or 1,5 Pentylene and the like.

Oxy-Cm-Cn-alkylene represents a group -OR-, wherein R is C _m -C _n -alkylene. Thus, oxy-C2-C4-alkylene is a group -OR-, wherein R is C2-C4-alkylene. Examples of these are oxyethylene, oxypropylene and the like.

Oxy-Cm-Cn-Alkylenoxy represents a group -ORO-, wherein R is C _m -C _n -alkylene. Thus, oxy-C 2 -C 4 -alkyleneoxy represents a group -ORO- in which R is C 1 -C 3 -alkylene. Examples of these are oxymethyleneoxy, oxy-1,2-ethyleneoxy, oxy-1,3-propyleneoxy and the like

Cm-Cn alkenylene is a linear or branched alkenylene group with m to n, e.g. 2 to 8, carbon atoms and a C-C double bond at any position. For example, C 1 -C 4 -alkenylene is 1, 1 or 1, 2-ethenylene, 1, 1, 1, 2 or 3

1, 3-propenylene, 1, 1, 1, 2, 1, 3 or 1, 4-butylene. C 3 -C 8 -alkenylene is, for example, 1, 1, 1, 2 or 1, 3-propenylene, 1, 1, 1, 2, 1, 3 or 1, 4-butenylene, 1, 1, 1, 2, 1, 3, 1, 4 or 1, 5-pentenylene and the like. Oxy-Cm-Cn-alkenylene is a group -OR-, wherein R is C _m -C _n -alkenylene. Thus, oxy-C2-C4 alkenylene is an -OR- group, where R is C2-C4 alkenylene. Examples of these are oxyethenylene, oxypropenylene and the like.

Oxy-Cm-Cn-alkenyleneoxy represents a group -OR-O-, wherein R is C _m -C _n -alkenylene. Thus, oxy-C2-C4 alkenyleneoxy represents a group -O-RO- wherein R is C2-C4 alkenylene. Examples of these are oxyethenyleneoxy, oxypropenyleneoxy and the like.

Cm-Cn alkynylene is a linear or branched alkynylene group with m to n, e.g. 2 to 8, carbon atoms and a C-C triple bond at any position. For example, C 1 -C 4 -alkynylene is 1, 1 or 1, 2-ethynylene, 1, 1, 1, 2 or 1, 3-propynylene, 1, 1, 1, 2, 1, 3 or 1,4-butynylene. C 3 -C 5 -alkynylene is, for example, 1, 1, 1, 2 or 1, 3-propynylene, 1, 1, 1, 2, 1, 3 or 1, 4-butynylene, 1, 1, 1, 2, 1, 3, 1, 4 or 1, 5-pentynylene and the like.

C 1 -C 4 -alkanols (= C 1 -C 4 -alcohols) are, in the context of the present invention, aliphatic C 1 -C 4 -hydrocarbons in which a hydrogen atom has been replaced by a hydroxyl group. Examples of these are methanol, ethanol, propanol, isopropanol, n-butanol, sec-butanol, isobutanol and tert-butanol.

Aryl is an optionally substituted aromatic hydrocarbon radical having 6 to 14 carbon atoms, such as phenyl, naphthyl, anthracenyl or phenanthrenyl and in particular phenyl. Suitable substituents are, for example, halogen, C 1 -C 6 -alkyl, C 1 -C ₈ -alkoxy, OH, NO ₂ , CN, COOH, C 1 -C 6 -alkylcarbonyl, C 1 -C ₈ -

Alkylcarbonyloxy, Ci-Cs-Alkyloxycarbonyl, NH2, d-Cs-alkylamino, di- (Ci-Cs-AIkVl) - amino and other substituents mentioned below.

Aryloxy is an aryl radical bonded via an oxygen atom. An example of this is optionally substituted phenoxy.

Arylthio represents an aryl radical bonded via a sulfur atom. An example of this is optionally substituted phenylthio.

Aryl-d-Cs-alkyl is a Ci-Cs-alkyl radical in which a hydrogen atom is substituted by an aryl group. Examples of these are benzyl and 2-phenylethyl.

Aryl-C2-C8 alkenyl is a C2-C8 alkenyl radical in which a hydrogen atom is substituted by an aryl group. An example of this is 2-phenylethenyl (styryl). Aryl-C 2 -C 8 -alkynyl is a C 2 -C 8 -alkynyl radical in which a hydrogen atom is substituted by an aryl group. An example of this is 2-phenylethynyl.

Aryl-C-i-Cs-alkoxy is a Ci-Cs-alkoxy radical in which a hydrogen atom is substituted by an aryl group.

Arylthio-C 1 -C 4 -alkyl is a C 1 -C 4 -alkyl radical in which a hydrogen atom is substituted by an aryl group, for example optionally substituted phenylthio-C 1 -C 4 -alkyl. Examples of optionally substituted phenylthio-C ₁ -C ₄ -alkyl are phenylthiomethyl (C ₆ H ₅ -S-CH ₂ ) and phenylthioethyl (C ₆ H ₅ -S-CH ₂ CH ₂ ), where the phenyl radical may be substituted, for example by a or more chlorine atoms.

Heterocyclyl is a non-aromatic saturated or unsaturated or aromatic ("hetaryl") heterocyclyl radical having preferably 3 to 7 ring members and 1, 2, 3 or 4 heteroatoms which are selected from O, N and S and / or heteroatoms. groups of atoms which are selected from SO, SO ₂ and NR, in which R is H or C 1 -C 8 -alkyl, as ring members and also, if appropriate, 1, 2 or 3 carbonyl groups as ring members Examples of nonaromatic heterocyclyl groups include pyridinyl, azidinyl, pyrrolidinyl, pyrrolidinonyl, pyrrolidinedi nyl, pyrazolinyl, pyrazolinyl, imidazolinyl, imidazolinonyl, imidazolinedionyl, pyrrolinyl, pyrrolinonyl, pyrrolinediyl, pyrazolinyl, imidazolinyl, imidazolinonyl, tetrahydrofuranyl, dihydrofuranyl, 1,3-dioxolanyl, dioxolenyl, thiolanyl, Dihydrothienyl, oxazolidinyl, isoxazolidinyl, oxazolinyl, isoxazolinyl, thiazolinyl, isothiazolinyl, thiazolidinyl, isothiazolidinyl, oxathiolanyl, piperidinyl, piperidinone yl, piperidinedione, piperazinyl, pyridinonyl, pyridinedione, pyridazzinonyl, pyridazinedionyl, pyrimidinonyl, pyridazinedionyl, pyranyl, dihydropyranyl, tetrahydropyranyl, dioxanyl, thiopyranyl, dihydrothiopyranyl, tetrahydrothiopyranyl, morpholinyl, thiazinyl and the like. Examples of aromatic heterocyclyl groups (hetaryl) include pyrrolyl, furyl, thienyl, pyrazolyl, imidazolyl, triazolyl, tetrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, thiadiazolyl, oxadiazolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl and triazinyl.

Heterocyclyloxy or hetaryloxy is a heterocyclyl or hetaryl radical bonded via an oxygen atom.

Hetaryl-Ci-Cs-alkyl is a Ci-Cs-alkyl radical in which a hydrogen atom is substituted by a hetaryl group. Examples of these are pyrrolylmethyl, pyridinylmethyl and the like. Hetaryl-C2-C8 alkenyl is a C2-C8 alkenyl radical in which a hydrogen atom is substituted by a hetaryl group.

Hetaryl-C 2 -C 8 -alkynyl is a C 2 -C 8 -alkynyl radical in which a hydrogen atom is substituted by a hetaryl group.

Hetaryl-d-Cs-alkoxy is a C 1 -C 8 -alkoxy radical in which a hydrogen atom is substituted by a hetaryl group.

The above and the following statements on preferred features of the invention apply both on their own and in combination with other preferred features.

"Increasing the quality" preferably means that at least one oil crop produces at least one of the criteria (i) to (xi), more preferably (i) to (viii), even more preferably (i) to (vii), especially (i ) to (iii) and (vi), especially (i), (ii) or (vi) and even more specifically (i) or (vi).

Suitable oil plants are, for example, oilseed rape, turnip rape, mustard, oil radish, camelina, Ölrauke, Krambe, sunflower, safflower, thistle, marigold, soybean, lupine, flax, hemp, pumpkin, poppy, corn, oil palm and peanut.

The oil plants are preferably selected from seed oil plants in the narrower sense.

Seed oil plants are preferably selected from oilseed rape, turnip rape, mustard, oil radish, camelina, oil ilex, raspberry, sunflower, safflower, thistle, marigold, soybean, lupine, flax, hemp, pumpkin, poppy and corn.

Particularly preferred are the oil plants / seed oil plants selected from rapeseed, turnip rape, sunflower, soybean, linseed and corn, more preferably rapeseed, turnip rape and sunflower, even more preferably rapeseed and turnip rape and in particular rape.

Especially for an application in the food and animal feed sector, oilseed rape and in particular oilseed rape are preferred. For other applications, other types of rapeseed, such as erucic acid and glucosinolate-containing varieties are suitable. The fungicides used according to the invention are selected from aryl and heterocyclylamides (also referred to below as amide fungicides), carbamates, dicarboximides, azoles, strobilurins and morpholines. In one embodiment of the invention, the fungicides used are selected from aryl and heterocyclylamides, carbamates, dicarboximides, azoles and strobilurins. The fungicides used according to the invention are preferably selected from aryl and heterocyclylamides, strobilurins and azoles. The fungicides used according to the invention are particularly preferably selected from aryl and heterocyclylamides and azoles. Specifically, at least one aryl or heterocyclylamide is used in combination with at least one azole.

Aryl- and heterocyclylamides (amide fungicides) are understood as meaning fungicides which comprise a carboxamide group in which the amine part is derived from optionally substituted aniline or from an optionally substituted hetarylamine and the carbonyl group carries an optionally substituted aryl or heterocyclyl radical.

Amide fungicides, also referred to as carboxamide fungicides or especially in the case where the amine portion of aniline is derived, are known as anilide fungicides, and methods for their preparation are generally known to those skilled in the art and, for example, in Farm Chemicals Handbook, Meister Publishing Company or in the Compendium of Pesticide Common Names, http://www.hclrss.demon.co.uk/, which is incorporated herein by reference in its entirety.

Preferred amide fungicides are those of the formula I.

A-CO-NH-MQR ¹ where

A is an aryl group or an aromatic or non-aromatic 5- or 6-membered heterocycle containing 1 to 3 heteroatoms or heteroatom-containing

Groups which are selected from O, S, N and NR ² , wherein R ^{2 is} hydrogen or Ci-Cs-alkyl, contains as ring members, wherein the aryl group or the heterocycle optionally have 1, 2 or 3 substituents independently are selected from halogen, Ci-Cs-alkyl, Ci-Cs-haloalkyl, Ci-Cs- alkoxy, Ci-Cs-haloalkoxy, Ci-Cs-alkylthio, Ci-Cs-alkylsulfinyl and Ci-C ₈ -

alkylsulfonyl;

M is a thienyl ring or a phenyl ring, wherein the thienyl and the phenyl ring can carry 1, 2 or 3 halogen atoms and wherein the phenyl ring optionally condensed with a saturated 5-membered ring optionally substituted by 1, 2 or 3 C 1 -C 6 -alkyl groups and / or optionally having a heteroatom selected from O and S as the ring member;

Q is a bond, Ci -C ₆ -alkylene-Al, C2-C6-alkenylene, C2-C6 alkynylene, C3-C6 cycloalkylene, _C3-C6 cycloalkenylene, -O-C1 -C ₆ -alkylene-Al, -OC ₂ -C ₆ alkenylene, -OC ₂ -C ₆ alkynylene, -O-Cs-Ce-cycloalkylene, -O-Cs-Ce-cycloalkenylene, -S-CrC ₆ -alkylene, -SC ₂ -C ₆ alkenylene, -S-C ₂ -C ₆ alkynylene, -S-Cs-Ce-cycloalkylene, -SC ₃ -C ₆ - kylen cycloalkenylene, -SO-Ci-C ₆ -AI, -SO-C ₂ -C ₆ - Alkenylene, -SO-C ₂ -C ₆ -alkynylene, -

SO-Cs-Ce-cycloalkylene, -SO-Cs-Ce-cycloalkenylene, -SO ₂ -Ci-C ₆ -alkylene, -SO ₂ -C ₂ - Ce-alkenylene, -SO ₂ -C ₂ -C ₆ -alkynylene , -SO ₂ -C ₃ -C ₆ cycloalkylene, -SO ₂ -C ₃ -C ₆ - cycloalkenylene, O, S, SO or SO ₂ ;

wherein the aliphatic and cycloaliphatic radicals in Q may be partially or completely halogenated and / or the cycloaliphatic radicals may be substituted by 1, 2 or 3 C 1 -C -alkyl radicals;

R ^{1 is} hydrogen, halogen, C 3 -C ₆ -cycloalkyl or phenyl, where the cycloalkyl radical can carry one methyl group and where phenyl is replaced by 1 to 5 halogen atoms and / or by 1, 2 or 3 substituents which are selected independently of one another C 1 -C 6 -alkyl, C 1 -C 12 -haloalkyl, C 1 -C -alkoxy, C 1 -C 5 -haloalkoxy, C 1 -C -alkylthio and C 1 -C -haloalkylthio.

Amides of the formula I and processes for their preparation are known per se and, for example, in EP-A-545099, EP-A-589301, EP-A 737682, EP-A 824099, WO 97/08952, WO 99/09013, WO 03/010149, WO 03/070705, WO 03/074491, WO 2004/005242 and WO 2004/067515 and in the literature cited therein, to which reference is hereby fully made.

Preferably, the carboxamide group and the radical Q are bonded to adjacent carbon atoms of the radical M.

In a preferred embodiment, Q is a single bond and R ¹ is hydrogen.

In an alternative preferred embodiment, Q is a single bond and R ¹ is phenyl substituted by 1, 2 or 3 hydrogen atoms. In an alternatively preferred embodiment, Q is C ¹ -C 6 -alkylene and R ¹ is hydrogen.

In an alternatively preferred embodiment, Q and R ¹ together form -O-C1-C4-haloalkyl or -S-Ci-C ₄ -haloalkyl.

In an alternatively preferred embodiment, Q is cyclopropylene and R ¹ is cyclopropyl, optionally bearing a methyl group. Preferably, both rings are trans-substituted.

A is preferably selected from groups of the formulas (A1) to (A8) described below, and more preferably from groups of the formulas (A1), (A2), (A5) and (A7) described below.

In a preferred embodiment, M is thienyl.

In an alternatively preferred embodiment, M is phenyl. M preferably carries the radical QR ¹ as the only substituent. Alternatively, preferably M carries a halogen atom in addition to the radical QR ¹ , fluorine being preferred among these. Preferably, the halogen atom is bonded in the para position to the carboxamide group.

The amide of the formula I is particularly preferably selected from anilides of the formula 1.1

)

wherein A is a group of the formula A1 to A8

(A1) (A2) (A3)

(A7) (A8)

stands in which

X is CH ₂ , S, SO or SO ₂ ;

R ^{3 is} CH ₃ , CHF ₂ , CF ₃ , Cl, Br or I;

R ^{4 is} CF ₃ or Cl;

R ^{5 is} hydrogen or CH ₃ ;

R ^{6 is} CH ₃ , CHF ₂ , CF ₃ or Cl;

R ^{7 is} hydrogen, CH ₃ or Cl;

R ^{8 is} CH ₃ , CHF ₂ or CF ₃ ;

R ^{9 is} hydrogen, CH ₃ , CHF ₂ , CF ₃ or Cl; and

R ^{10 is} C 1 -C ₄ -alkyl, C 1 -C ₄ -alkoxy, C 1 -C ₄ -alkylthio or halogen.

Preferably, the group A stands for the group A2, wherein R ^{4 is} halogen. Preferably, R ^{10 is} simultaneously halogen.

In particular, the amide fungicide of the formula I is selected from anilides of the formula 1.1.1 and 1.1.2

(1.1 .1) (1.1 .2)

Of these, the anilide 1.1.1 is particularly preferred. This compound is also known under the common name Boscalid and commercially available.

Alternatively preferred are amides I, wherein A is a radical of the formula (A1) to (A8), M is phenyl or thienyl, Q is C ¹ -C 6 -alkylene and R ^{1 is} hydrogen.

Alternatively preferred are amides I, wherein A is a radical of the formula (A1) to (A8), M is phenyl, Q is cyclopropylene and R ^{1 is} cyclopropyl, which optionally carries a methyl group. Preferably, both rings are trans-substituted.

In addition to the anilides (1.1), in particular (1.1.1) and (1.1.2) are particularly preferred

Connections selected under:

2-iodo-N-phenyl-benzamide, 2-chloro-N- (4'-chloro-biphenyl-2-yl) -nicotinamide,

N- [2- (1,3-dimethyl-butyl) -thiophen-3-yl] -3-trifluoromethyl-1-methyl-pyrazol-4-yl-carboxamide,

N- (2-bicyclopropyl-2-yl-phenyl) -3-difluoromethyl-1-methylpyrazole-4-ylcarboxamide,

N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) -1,3-dimethylpyrazol-4-ylcarboxamide,

N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) -1,3-dimethyl-5-fluoropyrazol-4-ylcarboxamide,

N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) -5-chloro-1,3-dimethylpyrazol-4-ylcarboxamide,

N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) -3-fluoromethyl-1-methylpyrazole-4-ylcarboxamide,

N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) -3- (chloro fluoromethyl) -1-methylpyrazole-4-ylcarboxamide,

N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) -3-difluoromethyl-1-methylpyrazole-4-ylcarboxamide,

N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) -3-difluoromethyl-5-fluoro-1-methylpyrazole-4-ylcarboxamide,

N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) -5-chloro-3-difluoromethyl-1-methylpyrazole-4-ylcarboxamide,

N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) -3- (chlorodifluoromethyl) -1-methylpyrazole-4-ylcarboxamide, N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) -1-methyl-3-trifluoromethylpyrazole-4-yl-carboxamide,

N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) -5-fluoro-1-methyl-3-trifluoromethylpyrazole-4-yl-carboxamide,

N- (3 ', 4', 5'-trifluorobiphenyl-2-yl) -5-chloro-1-methyl-3-trifluoromethylpyrazole-4-ylcarboxamide, N- (2 ', 4', 5'-trifluorobiphenyl-2 -yl) -1,3-dimethylpyrazol-4-ylcarboxamide,

N- (2 ', 4', 5'-trifluorobiphenyl-2-yl) -1,3-dimethyl-5-fluoropyrazol-4-ylcarboxamide,

N- (2 ', 4', 5'-trifluorobiphenyl-2-yl) -5-chloro-1, 3-dimethylpyrazol-4-ylcarboxamide,

N- (2 ', 4', 5'-trifluorobiphenyl-2-yl) -3-fluoromethyl-1-methylpyrazole-4-ylcarboxamide,

N- (2 ', 4', 5'-trifluorobiphenyl-2-yl) -3- (chlorofluoromethyl) -1-methylpyrazol-4-ylcarboxamide, N- (2 ', 4', 5'-trifluorobiphenyl-2-yl ) -3-difluoromethyl-1-methylpyrazol-4-ylcarboxamide,

N- (2 ', 4', 5'-trifluorobiphenyl-2-yl) -3-difluoromethyl-5-fluoro-1-methylpyrazole-4-ylcarboxamide,

N- (2 ', 4', 5'-trifluorobiphenyl-2-yl) -5-chloro-3-difluoromethyl-1-methylpyrazole-4-ylcarboxamide,

N- (2 ', 4', 5'-trifluorobiphenyl-2-yl) -3- (chlorodifluoromethyl) -1-methylpyrazol-4-ylcarboxamide, N- (2 ', 4', 5'-trifluorobiphenyl-2-yl ) -1-methyl-S-trifluoromethylpyrazoleM-ylcarboxamide,

N- (2 ', 4', 5'-trifluorobiphenyl-2-yl) -5-fluoro-1-methyl-3-trifluoromethylpyrazole-4-yl-carboxamide,

N- (2 ', 4', 5'-trifluorobiphenyl-2-yl) -5-chloro-1-methyl-3-trifluoromethylpyrazole-4-ylcarboxamide,

N- (3 ', 4'-dichloro-3-fluorobiphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide,

N- (3 ', 4'-dichloro-3-fluorobiphenyl-2-yl) -1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxamide,

N- (3 ', 4'-difluoro-3-fluorobiphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide,

N- (3 ', 4'-Difluoro-3-fluorobiphenyl-2-yl) -1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxamide, N- (3'-chloro-4'-fluoro 3-fluorobiphenyl-2-yl) -1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxamide,

N- (3 ', 4'-dichloro-4-fluorobiphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide,

N- (3 ', 4'-Difluoro-4-fluorobiphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N- (3', 4'-dichloro-4- fluorobiphenyl-2-yl) -1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxamide,

N- (3 ', 4'-difluoro-4-fluorobiphenyl-2-yl) -1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxamide,

N- (3'-chloro-4'-fluoro-4-fluorobiphenyl-2-yl) -1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxamide, N- (3 ', 4'-dichloro 5-fluorobiphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide,

N- (3 ', 4'-difluoro-5-fluorobiphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide,

N- (3 ', 4'-dichloro-5-fluorobiphenyl-2-yl) -1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxamide, N- (3 ', 4'-Difluoro-5-fluorobiphenyl-2-yl) -1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxamide, N- (3', 4'-dichloro-5- fluorobiphenyl-2-yl) -1,3-dimethyl-1H-pyrazole-4-carboxamide, N- (3'-chloro-4'-fluoro-5-fluorobiphenyl-2-yl) -1-methyl-3- difluoromethyl-1H-pyrazole-4-carboxamide, N- (4'-fluoro-4-fluorobiphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N- (4 ' Fluoro-5-fluorobiphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N- (4'-chloro-5-fluorobiphenyl-2-yl) -1-methyl- 3-trifluoromethyl-1H-pyrazole-4-carboxamide, N- (4'-methyl-5-fluorobiphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N- ( 4'-fluoro-5-fluorobiphenyl-2-yl) -1,3-dimethyl-1H-pyrazole-4-carboxamide, N- (4'-chloro-5-fluorobiphenyl-2-yl) -1, 3 Dimethyl-1H-pyrazole-4-carboxamide, N- (4'-methyl-5-fluorobiphenyl-2-yl) -1, 3-dimethyl-1H-pyrazole-4-carboxamide, N- (4'-fluoro -6-fluorobiphenyl-2-yl) -1-methyl-3-trifluoromethyl-1H-pyrazole-4-carboxamide, N- (4'-chloro-6-fluorobiphenyl-2-yl) -1-methyl-3- trifluoromethyl-1H-pyrazole-4-carboxa mid, N- [2- (1,1,3,3,3-hexafluoropropoxy) -phenyl] -3-d-fluoromethyl-1-methyl-1H-pyrazole-4-carboxamide,

N- [4 '- (trifluoromethylthio) biphenyl-2-yl] -3-d-isluoromethyl-1-methyl-1H-pyrazole-4-carboxamide, and

N- [4 '- (trifluoromethylthio) -biphenyl-2-yl] -1-methyl-3-trifluoromethyl-1-methyl-1H-pyrazole-4-carboxamide.

Carbamate fungicides are fungicidally active compounds containing a carbamate group (NRR'-CO-OR ").

Carbamate fungicides and processes for their preparation are generally known to the person skilled in the art and are described, for example, in Farm Chemicals Handbook, Meister Publishing Company or in the Compendium of Pesticide Common Names, http://www.hclrss.demon.co.uk/ is hereby incorporated by reference.

Preferred carbamate fungicides are those known by the common names benthicillicarbic acid, furophanate, iprovalicarb, propamocarb, thiophanate, thiophanate-methyl, thiophanate-ethyl, benomyl, carbendazim, cypendazole, debacarb and mecarbarbid. Among them, carbendazim, thiophanate, thiophanate-methyl and thiophanate-ethyl are particularly preferred. In particular, thiophanate-methyl is used.

Dicarboximide fungicides are fungicidally active compounds containing an imide group of a dicarboxylic acid. Accordingly, these compounds contain a cyclic structure having a -CO-NR-CO group. Dicarboximide fungicides and processes for their preparation are generally known to those skilled in the art and are described, for example, in Farm Chemicals Handbook, Meister Publishing Company or in the Compendium of Pesticide Common Names, http://www.hclrss.demon.co.uk/, which is hereby incorporated by reference Full reference is made.

Preferred dicarboximides are those of the formula II

O

In which

A is -CR ¹² R ¹³ -CR ¹⁴ R ¹⁵ -, -CR ¹² R ¹³ -O-, -CR ¹² R ¹³ -NR ¹⁶ - or -CR ¹² = CR ¹⁴ -,

R ¹¹ is C 1 -C 6 -alkylthio, C 1 -C ₈ -haloalkylthio, C 1 -C ₈ -alkylthio-C 1 -C ₄ -alkyl, C 1 -C ₈ -

Haloalkylthio-Ci-C4-alkyl, phenylthio, phenylthio-Ci-C4-alkyl, phenyl, phenylamino, where phenyl in the four last-mentioned radicals may be partially or completely halogenated and / or 1 to 3 substituents which are selected from Halogen, C 1 -C ₈ -alkyl, C 1 -C ₈ -alkoxy, phenyl and phenoxy, may be di- (C 1 -C ₈ -alkyl) phosphonate or di- (C 1 -C ₈ -alkyl) thiophosphonate stands;

R ¹² , R ¹³ , R ¹⁴ and R ¹⁵ independently of one another represent hydrogen, halogen, C 1 -C ₈ -alkyl,

_{Ci-C8-haloalkyl, Ci-C8-alkoxy, Ci-C8} alkylthio, _{Ci-C8-haloalkoxy,} CrC ₈ - haloalkylthio, Ci-C ₈ alkoxy-Ci-C ₈ alkyl, C ₂ - C ₈ -alkenyl, C ₂ -C ₈ -alkynyl, carboxy (=

COOH), C 1 -C ₈ -alkyloxycarbonyl, C 1 -C ₈ -alkylcarbonyl, C 1 -C ₈ -alkylcarbonyloxy, phenyl which may be partially or completely halogenated and / or 1 to 3 substituents which are selected from halogen, C 1 -C ₈ Alkyl, C 1 -C ₈ alkoxy, phenyl, phenoxy, benzyl and benzyloxy,

in which R ¹² and R ^{14 may} also together with the carbon atoms to which they are attached form a 3- to 6-membered saturated or unsaturated aromatic or non-aromatic cycle which is unsubstituted or substituted by 1 to 3 substituents which are selected from Halogen, Ci-Ce-alkyl, d-Cs-alkoxy, phenyl, phenoxy, benzyl or benzoxy may be substituted; and

R ^{16 is} hydrogen, C 1 -C ₄ -alkyl, C 1 -C ₈ -alkylcarbonyl, C 1 -C ₈ -alkyloxycarbonyl or C 1 -C ₈ -alkylaminocarbonyl or di- (C 1 -C ₈ -alkyl) aminocarbonyl.

Preferred dicarboximide fungicides are those known by the common names famoxadone, fluoroimides, chlozolinates, dichlozolines, iprodione, isovalediones, myclozolin, procymidones, vinclozolin, captafol, captan, ditalimfos, folpet and thiochlorfenphim. Particularly preferred are iprodione, vinclozolin, and procymidone. In particular, Iprodione is used.

Azole fungicides, also referred to as conazole fungicides, are fungicidally active compounds containing an aromatic 5-membered nitrogen heterocycle and especially an imidazole ring ("imidazole-conazole") or a triazole ring ("triazole-conazole").

Azole fungicides and processes for their preparation are generally known to those skilled in the art and are described, for example, in Farm Chemicals Handbook, Meister Publishing Company or in the Compendium of Pesticide Common Names, http://www.hclrss.demon.co.uk/, which is hereby incorporated by reference Full reference is made.

Preferred azole fungicides are those which are known under the common names bitertanol, bromoconazole, cyproconazole, difenoconazole, dinitroconazole, epoxiconazole, fenbuconazole, fluquiconazole, flusilazole, hexaconazole, imazalil, metconazole, myclobutanil, pacobutrazole, penconazole, propiconazole, prochloraz, Prothioconazole, tebuconazole, triadimefon, triadimol, triflumizole and triticonazole. Particularly preferred are difenoconazole, flusilazole, metconazole, paclobutrazole, prothioconazole and tebuconazole. More preferred are flusilazole, metconazole, prothioconazole and tebuconazole. Even more preferred are metconazole, prothioconazole and tebuconazole. In particular, one uses metconazole.

Strobilurin fungicides are fungicidally active compounds derived from natural strobilurins, antibodies produced by fungi of the genus Strobilurus (cone ruffians). Structurally they contain 1.) at least one functional group selected from enol ethers, oxime ethers and O-alkylhydroxylamines (Group I) and 2.) at least one carboxyl derivative (Group II). Preferred carboxyl derivatives are the following functional groups: ester, cyclic ester, amide, cyclic amide, hydroxamic acid and cyclic hydroxamic acid. The radicals of group I and of group II are preferably directly adjacent, ie connected by a single bond.

Strobilurin fungicides are generally known to the person skilled in the art and are described, for example, in Farm Chemicals Handbook, Meister Publishing Company or in the Compendium of Pesticide Common Names, http://www.hclrss.demon.co.uk/, to which reference is hereby made in its entirety ,

Preferred strobilurins are those of the formulas INA or HIB

INA HIB

wherein

_LJ _ ^ is a double bond or single bond;

R ^{a is} -C [CO ₂ CHs] = CHOCH ₃ , -C [CO ₂ CHs] = NOCH ₃ , -C [CONHCHS] = NOCH ₃ , -C [CO ₂ CHS] = CHCHS, -C [CO ₂ CHS ] = CHCH ₂ CH ₃ , -C [CO ₂ CHS] = NOCH ₃ , -C [COCH ₂ CHS] = NOCH ₃ , -N (OCHS) -CO ₂ CH ₃ , -N (CHS) -CO ₂ CH ₃ or -N (CH ₂ CHs) -CO ₂ CH ₃ ;

R ^{b is} an organic radical which is bonded directly or via an oxygen atom, a sulfur atom, an amino or a C 1 -C 8 -alkylamino group; or the

together with a group X and the ring Q or T to which they are attached, an optionally substituted bicyclic, partially or completely unsaturated system which, in addition to carbon ring members, has 1, 2 or 3 heterocyclic atoms, independently selected from oxygen, sulfur and nitrogen, may contain;

R ^{c is} -OC [CO ₂ CHS] = CHOCH ₃ , -OC [CO ₂ CHS] = CHCH ₃ , -OC [CO ₂ CHS] = CHCH ₂ CHS, -SC [CO ₂ CHS] = CHOCHS ₁ -SC [ CO ₂ CHS] = CHCHS, -SC [CO ₂ CHS] = CHCH ₂ CHS,

-N (CHS) C [CO ₂ CHS] = CHOCHS ₁ -N (CHS) C [CO ₂ CHS] = NOCHS, -CH ₂ C [CO ₂ CHS] = CHOCHS, -CH ₂ C [CO ₂ CHS] = NOCHS or -CH ₂ C [CONHCHS] = NOCHS;

R ^{d is} oxygen, sulfur, = CH- or = N-;

n is O, 1, 2 or 3, where X may be the same or different when n> 1;

X is cyano, nitro, halogen, C -C -alkyl ₈ -alkyl, Ci-C ₈ haloalkyl, _{Ci-C8-alkoxy,} Ci-C ₈ - haloalkoxy or C ₈ -alkylthio or

when n> 1, a Cs-Cδ-alkylene, Cs-Cs-alkenylene, oxy-C ₂ -C 4 -alkylene, oxy-C ₁ -C 3 -alkyleneoxy, oxy bonded to two adjacent C atoms of the phenyl ring C ₂ -C 4 -alkenylene-, oxy-C ₂ -C 4 -alkenylenoxy- or butadienediyl group, these chains in turn may carry one to three radicals which are independently selected from halogen, Ci-C ₈ alkyl, ci C ₈ haloalkyl, _{Ci-C8-alkoxy, Ci-C8-haloalkoxy} and Ci-C ₈ alkylthio;

Y is = C- or -N-;

Q is phenyl, pyrrolyl, thienyl, furyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, thiadiazolyl, triazolyl, pyridinyl, 2-pyridonyl, pyrimidinyl or triazinyl; and

T is phenyl, oxazolyl, thiazolyl, thiadiazolyl, oxadiazolyl, pyridinyl, pyrimidinyl or triazinyl.

Wherein the substituents R ^b, these are in particular a Ci-C ₈ alkyl, C ₂ -C ₈ alkenyl, C ₂ -C ₈ alkynyl, aryl, hetaryl, aryl-Ci-C ₈ alkyl, hetaryl-C ₁ -C ₈ -alkyl, aryl-C ₂ -C ₈ -alkenyl, hetaryl-C ₂ -C ₈ -alkenyl, aryl-C ₂ -C ₈ -alkynyl or hetaryl-C C ₂ -C ₈ -alkynyl radical, which is optionally interrupted by one or more groups selected from O, S, SO, SO ₂ , NR (R =H or C ₁ -C ₆ -alkyl), CO, COO, OCO, CONH, NHCO and NHCONH or a residue of the formulas as defined below CH ₂ ON = CR ^α CR ^β or CH ₂ ON = CR ^γ CR ^δ = NOR ^ε . Optionally, these radicals also have one or more (preferably 1, 2 or 3) substituents independently of one another selected from C 1 -C 6 -alkyl, C 1 -C 5 -alkoxy, halogen, cyano, C 1 -C 5 -haloalkyl (in particular CF 3 and CHF2), hetaryl and aryl. In turn, hetaryl and aryl may again have 1, 2 or 3 substituents which are selected independently of one another from halogen, C 1 -C -haloalkyl (in particular CF 3 and CHF 2), phenyl, CN, phenoxy, C 1 -C ₈ -alkyl, _Ci-C8-alkoxy and _{Ci-C8-haloalkoxy.}

Such compounds are known and described, for example, in WO 97/10716 and in the literature cited therein, to which reference is hereby fully made.

Preference is given to strobilurins of the formulas INA or HIB in which R ^{b is} aryloxy, hetaryloxy, aryloxymethylene, hetaryloxymethylene, arylethenylene or hetarylethenylene, where these radicals optionally have 1, 2 or 3 substituents which are selected independently of one another from C 1 -C ₈ alkyl, halogen, CF3, CHF2, CN, Ci-C ₈ alkoxy and phenyl which may itself have 1, 2 or 3 substituents independently selected from halo, CF3, CHF2, phenyl, CN, phenoxy, C -C ₈ - alkyl, _Ci-C8-alkoxy and _{Ci-C8-haloalkoxy;}

or R ^{b is} CH ₂ ON = CR ^α R ^β or CH ₂ ON = CR ^γ CR ^δ = NOR ^ε ,

in which

R ^α is d-Ce-alkyl;

R is ^ß, which optionally has 1, 2 or 3 substituents independently selected from Ci-C ₈ alkyl, _Ci-C8 alkoxy, halogen, _{Ci-C8-haloalkoxy,} phenyl, pyridyl or pyrimidyl, CF3 and CHF2;

R ^γ for Ci-Ce-alkyl, _Ci-C8 alkoxy, halogen, _{Ci-C8-haloalkyl,} or hydrogen;

R ^δ is hydrogen, cyano, halogen, Ci-C ₈ -alkyl, _C-8 alkoxy, _Ci-C8 alkylthio, d- _{C8-alkylamino,} di-Ci-C ₈ alkylamino, C ₂ - C ₈ alkenyl, C ₂ -C ₈ alkenyloxy, C ₂ -C ₈ -

Alkenylthio, C ₂ -C ₈ -alkenylamino, NC ₂ -C ₈ alkenyl-N-Ci-C ₈ alkylamino, C ₂ -C ₈ - alkynyl, C ₂ -C ₈ alkynyloxy, C ₂ -C ₈ alkynylthio , C ₂ -C ₈ -alkynylamino, NC ₂ -C ₈ alkynyl N-Ci-C ₈ alkylamino, wherein the hydrocarbon radicals of these groups to be partially or fully halogenated and / or 1, 2 or 3 radicals carry kön- NEN, which are independently selected from cyano, nitro, hydroxy, C 1 -C 8 -alkoxy, C 1 -C -haloalkoxy, C 1 -C 5 -alkoxycarbonyl, C 1 -C 8 -alkyl, C 1 -C 5 -alkylamino, C 1 -C 8 -cyclo alkylamino, C 2 -C 8 -alkenyloxy, C 3 -C -cycloalkyl, C 5 -C -cycloalkyloxy, heterocyclyl, heterocyclyloxy, aryl, aryloxy, aryl-C 1 -C -alkoxy, hetaryl, hetaryloxy and hetaryl-C 1 -C -alkoxy, where the cyclic radicals may in turn be partially or completely halogenated and / or carry 1, 2 or 3 groups which are independently selected from cyano, nitro, hydroxy, C ₁ -C 8 -alkyl, C ₁ -C 8 -haloalkyl, C ₃ -C ₈ -cycloalkyl, Ci-Cs-alkoxy, d-Cs-haloalkoxy, Ci-C ₈ - alkoxycarbonyl, Ci-Cs-alkylthio, Ci-Cs-alkylamino, di-Ci-Cs-alkylamino, C ₂ -C ₈ - alkenyl and C ₂ -C ₈ alkenyloxy;

or

for Cs-Cs-cycloalkyl, Cs-Cs-cycloalkyloxy, Cs-Cs-cycloalkylthio, C ₃ -C ₈ -cycloalkylamino, N-C3-Cs-cycloalkyl-N-C ₁ -C -alkylamino, heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino , N-heterocyclyl-N-Ci-Cs alkylamino, aryl, aryloxy, arylthio, arylamino, N-aryl-N-Ci-Cs-alkylamino, hetaryl, hetaryloxy, hetarylthio, hetarylamino or N-hetaryl-N-Ci-Cs Alkylamino, wherein the cyclic radicals may be partially or completely halogenated and / or carry 1, 2 or 3 groups which are independently selected from cyano, nitro, hydroxy, Ci-Cs-alkyl, Ci-Cs-haloalkyl, Cs -Cs-cycloalkyl, Ci-Cs-alkoxy, Ci-Cs-haloalkoxy, Ci-Cs-alkoxycarbonyl, Ci-Cs-alkylthio, Ci-Cs-alkylamino, di-Ci-Cs-alkylamino, C ₂ -Cs-Al kenyl , C 2 -C 8 -alkenyloxy, benzyl, benzyloxy, aryl, aryloxy, hetaryl and hetaryloxy, where the aromatic radicals themselves may be partially or completely halogenated and / or may carry 1, 2 or 3 of the following groups: cyano, C 1 -C 5 A alkyl, C 1 -C 8 haloalkyl, C 1 -C 8 alkoxy, nitro;

R ^{ε is} Ci-Cs-alkyl, C2-Cs-alkenyl or C2-Cs-alkynyl, where these groups can be partially or fully halogenated and / or 1, 2 or 3 of the following

Radicals can carry: cyano, Ci-Cs-alkoxy, Cs-Cs-cycloalkyl.

Particular preference is given to compounds of the formula INA or HIB in which R ^{b has} one of the following meanings:

a) phenyloxymethylene, pyridinyloxymethylene, pyrimidinyloxymethylene or pyrazolyloxymethylene, where the aromatic radical optionally has 1, 2 or 3 substituents, which are selected independently of one another from C 1 -C 8 -alkyl, halogen, CF ₃ , CHF ₂ , -C (CHs) = NOCH ₃ , and phenyl which is optionally substituted by 1, 2 or 3 halogen atoms and / or C 1 -C 8 -alkyl groups;

b) phenoxy or pyrimidinyloxy, which is optionally substituted by 1, 2 or 3 halogen atoms or a phenoxy radical which optionally has a halogen or cyano substituent;

c) phenylethenylene or pyrazolylethenylene, wherein the phenyl or pyrazolyl radical optionally has 1, 2 or 3 substituents which are selected independently from among halogen, CF3, CHF2 and phenyl.

d) CH ₂ ON = CR ^α R ^β ,

wherein

R ^α is d-Cs-alkyl; and

R ^{β is} phenyl which optionally has 1, 2 or 3 substituents which are independently selected from C 1 -C 6 -alkyl, halogen, CF 3 and CHF 2, or is pyrimidinyl which is optionally substituted by 1 or 2 C 1 -C -alkoxy radicals is substituted;

e) CH ₂ ON = CR ^γ CR ^δ = NOR ^ε , in which

R ^{γ is} C 1 -C ₈ -alkyl, C 1 -C ₈ -alkoxy or halogen;

R ^{δ is} C 1 -C ₈ -alkyl, cyano, halogen, C 1 -C ₈ -alkoxy, C 1 -C ₈ -alkenyl or phenyl which is optionally substituted by 1, 2 or 3 halogen atoms; and

R ^ε is d-Ce-alkyl.

Particular preference is given to compounds of the formula INA, in which Q is phenyl and n is 0.

Particularly preferred strobilurins are those known by the common names azoxystrobin, dimoxystrobin, fluoxastrobin, kresoxim-methyl, methaminostrobin, oryssastrobin, picoxystrobin, pyraclostrobin and trifloxystrobin. More preferred are pyraclostrobin, azoxystrobin and dimoxystrobin. Even more preferred are azoxystrobin and dimoxystrobin and especially dimoxystrobin. Morpholine fungicides are fungicidally active compounds that are a morpholine group

N o

contain.

Morpholine fungicides and methods for their preparation are generally known to the person skilled in the art and are described, for example, in Farm Chemicals Handbook, Meister Publishing Company or in the Compendium of Pesticide Common Names, http://www.hclrss.demon.co.uk/, which is hereby incorporated by reference Full reference is made.

Preferred morpholine fungicides are those known by the common names aldimorph, benzamorf, carbamorph, dimethomorph, dodemorph, fenpropimorph, fluoromorph and tridemorph. Of these, dimethomorph is particularly preferred.

The growth regulators are preferably selected from

(a) acylcyclohexanediones of the formula (IV)

wherein

R ^{A is} H or Ci-Cio-alkyl and

R ^B is d-Cio-alkyl or Cs-do-cycloalkyl

or salts thereof;

(b) Quaternary ammonium compounds of the formula (V)

wherein

R ^c and R ^D independently of one another are ^C 1 -C 10 -alkyl which is optionally substituted by at least one halogen atom, or ^C 3 -C 10 -cycloalkyl; or

R ^c and R ^D together represent a bridging unit - (CH 2) _n -,

- (CH ₂ ) 2-O- (CH ₂ ) 2- or - (CH ₂ ) -CH = CH- (CH ₂ ) -NH-,

wherein n is 4 or 5, and

Z "is a counter anion selected from halide ions, sulfate ions, C 1 -C 10 -alkylsulfonate ions, borate ions, carbonate ions and mixtures thereof;

(c) Ethephone (2-chloroethylphosphonic acid).

Sulfate ions are available for the pure sulfate anion SO ₄ ^{2 "} as well as for C1-C10

Alkyl sulfations RO-S (O) ₂ -O ", in which R is C 1 -C 10 -alkyl, for example methyl sulfate, ethyl sulfate and the like, preferably the pure sulfate anion SO ₄ ^2" .

Ci-Cio-Alkylsulfonationen stand for anions of the formula RS (O) ₂ -O ", wherein R is d-Cio-alkyl, for example methyl sulfonate, ethyl sulfonate and the like.

The borate anions are preferably those of the formula VI

1 / m - [M _x ByOz (A) Vr- - w (H ₂ O) (VI)

wherein

M is a cation of an agriculturally acceptable metal, a proton or ammonium; A is a chelating or complexing group associated with at least one boron atom or a cation M; x is a number from 0 to 10; y is a number from 1 to 48; z is a number from 0 to 48; v is a number from 0 to 24; m is a number from 1 to 6; w is a number from 0 to 24

M is preferably a cation of a metal selected from sodium, potassium, magnesium, calcium, zinc, manganese and copper, for a proton or for ammonium.

A is preferably selected from hydroxycarboxylic acids, carboxylic acids, alcohols, glycols, aminoalcohols, sugars and the like.

Suitable hydroxycarboxylic acids are e.g. Glycolic acid, lactic acid, mandelic acid, malic acid, tartaric acid, citric acid, other fruit acids and also hydroxyfatty acids such as ricinoleic acid.

Suitable carboxylic acids are monocarboxylic acids such as formic acid, acetic acid, propionic acid, valeric acid, isovaleric acid, caproic acid, enanthic acid, caprylic acid and other fatty acids, and dicarboxylic acids such as oxalic acid, malonic acid, succinic acid, adipic acid and the like.

Suitable alcohols are e.g. d-Cs-alcohols such as methanol, ethanol, propanol, isopropanol, n-butanol, sec-butanol, isobutanol, tert-butanol, pentyl alcohols such as pentanol and amyl alcohol, hexyl alcohols such as hexanol, heptyl alcohols such as heptanol and octyl alcohols such as octanol and 2-ethylhexanol.

Suitable glycols are e.g. C2-Cio-diols such as glycol, diethylene glycol, triethylene glycol and the like.

Suitable amino alcohols are e.g. Ethanolamine, diethanolamine, triethanolamine and the like.

Suitable sugars are, for example, the pentoses and hexoses, such as fructose, glucose, mannose and the like, and also the double sugars, such as sucrose. x is preferably 0, especially if M does not have one of the abovementioned preferred meanings.

y preferably represents a number from 2 to 20, more preferably from 2 to 10, more preferably from 3 to 10, even more preferably from 3 to 7 and in particular from 3 to 5. Specifically, y is 5.

z preferably represents a number from 6 to 10, particularly preferably from 6 to 8 and in particular 8.

v is preferably 0.

w is preferably from 2 to 10, more preferably from 2 to 8, and especially from 2 to 3.

m is preferably 1 or 2 and in particular 1.

Preferred are borates of formula (VI) wherein x is zero; or M is a cation of a metal selected from sodium, potassium, magnesium, calcium, zinc, manganese and copper, a proton or ammonium; and / or y is a number from 2 to 20, preferably from 2 to 10, particularly preferably from 3 to 10, more preferably from 3 to 7, in particular from 3 to 5; and / or z corresponds to a number from 6 to 10, in particular 6 to 8; and / or v is zero; and / or m is 1 or 2; and / or w is a number from 0 to 24.

Particular preference is given to borates of the formula (VI) in which y corresponds to a number from 3 to 7, in particular from 3 to 5; z is a number from 6 to 10, in particular 6 to 8, corresponds; v is zero; and w is a number from 2 to 10, especially from 2 to 8.

Very particular preference is given to borates of the formula (VI) in which y = 5; z = 8; v = 0; m = 1; w = 2 to 3 (pentaborates).

The charge balance, if necessary, is carried out in the borates via the cation M.

The borates may contain water, e.g. B. as water of crystallization in free or coordinated form or as bound water in the form of boron-bound hydroxy xygruppen. Suitable and preferred borates and processes for their preparation are known per se and described, for example, in WO 02/083732 and in the literature cited therein, to which reference is hereby fully made. Further suitable borates are described, for example, in WO 99/09832, to which reference is hereby fully made.

The compounds of formulas (IV) and (V) are known (see, for example, EP-A-123001, EP-A-126713, W. Rademacher, "Growth Retardants: Effects on Gibberellin Biosynthesis and Other Metabolic Pathways", Annu. Plant Mol. Biol. 2000, 51, 501-531).

The compounds of the formula (IV) can be present both in the trion form (triketo form) IV.a and in the tautomeric keto-enol forms IV.b or IV.c:

(IV.a) (IV.b) (IV.c)

In the compounds of the formula IV, R ^{A is} preferably H or C 1 -C ₄ -alkyl.

R ^B is preferably CrC ₄ -AlkVl or Cs-Cβ-cycloalkyl and in particular ethyl or cyclopropyl.

The salts of the acylcyclohexanedione compounds IV with R ^A * H are the salts of monoanions, while in the case of R ^A = H they can be both the salts of the mono- and the dianions of these compounds. The monoanions can be present both as carboxylate anions IV. D and as enolate anions IV. E or IV.f:

R ^A QOC

(IV.d) (IV.e) (IV.f) In dianion, the carboxylate and enolate groups are present side by side.

Preferred cations in the salts of the compounds of formula IV are the ions of the alkali metals, preferably of lithium, sodium and potassium, the alkaline earth metals, preferably of calcium and magnesium, and the transition metals, preferably of manganese, copper, zinc and iron, furthermore ammonium ( NH ₄ ⁺ ) and substituted ammonium, in which one to four hydrogen atoms are represented by C 1 -C ₄ -alkyl, hydroxy-C 1 -C ₄ -alkyl, C 1 -C ₄ -alkoxy-C 1 -C ₄ -alkyl, hydroxy-C 1 -C ₄ -alkoxy-C 1 -C ₄ -alkyl, phenyl or benzyl, preferably ammonium, methylammonium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tetramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2- (2-hydroxyeth-1 -oxy) eth-1 -ylammonium, di (2-hydroxyeth-1-yl) ammonium, benzyltrimethylammonium, benzyltriethylammonium, furthermore phosphonium ions, sulfonium mions, preferably tri (C 1 -C ₄ -alkyl) sulfonium such as trimethylsulfonium and sulfoxonium amides, ingenious and tri (C 1 -C ₄ -alkyl) sulfoxonium. Preferred cations are also chlormequat [(2-chloroethyl) trimethylammonium], mepiquat (N, N-dimethylpiperidinium) and N, N-dimethylmorpholinium. Particularly preferred cations are the alkali metal cations, the alkaline earth metal cations and the ammonium cation (NH ₄ ⁺ ). In particular, it is the calcium salt.

In the context of the present invention, the term "compounds of the formula IV", "acylcyclohexanediones of the formula IV" or "growth regulators of the formula IV" refers both to the neutral compounds IV and to their salts.

Particularly preferred compounds of IV used in the invention are prohexadione (R ^A = H, R ^B = ethyl) xapac, prohexadione-calcium (calcium salt of prohexadione) Trine- (R ^A = H, R ^B = cyclopropyl) and Trinexapac- Ethyl (R ^A = ethyl, R ^B = cyclopropyl).

In compounds of the formula (V), one of the radicals R ^c or R ^D is preferably ^C 1 -C 10 -alkyl and the other radical is ^C 1 -C 10 -alkyl which is substituted by a halogen atom, preferably by a chlorine atom. R ^{c is} particularly preferably methyl and R ^{D is} 2-chloroethyl.

In an alternative preferred embodiment, R ^c and R ^D together form a bridging unit - (CH 2) s-.

In a preferred embodiment of the invention, the anions Z in compounds V are selected from halide ions, sulfate ions and carbonate ions. In an alternative preferred embodiment of the invention, the anions Z in compounds V are selected from halide ions, especially chloride, borates, especially pentaborate, and mixtures thereof.

Z - particularly preferably represents a halide anion and in particular chloride.

In particular, the quaternary ammonium compounds of the formula (V) are the salt of chlormoquat (salt of 2-chloroethyltrimethylammonium), in particular chlormoquat chloride (2-chloroethyltrimethylammonium chloride) or the salt of mepiquat (salt of 1, 1-dimethylpiperidinium ), in particular mepiquat chloride (1, 1-dimethylpiperidinium chloride).

In addition, mixtures of the described growth regulators (IV), (V) and / or ethephon can be used.

Specifically, compounds (V) are used as growth regulators.

Two or more of the above-mentioned fungicides selected from the same class or different classes of fungicides may also be used in combination according to the invention. The combined use (referred to in the context of the present invention as well as combination of two or more fungicides) includes both the use of mixtures of different fungicides and their separate use, in which case the fungicides are used both simultaneously and successively, i. at a time interval of for example a few seconds to several months, can be used.

The fungicides to be used according to the invention are preferably selected from aryl and / or heterocyclylamides, strobilurins and azoles. With regard to suitable and preferred representatives of these fungicide classes, reference is made to the above statements. Also preferred is the combined use of at least two representatives of these fungicide classes. Specifically, at least one aryl or heterocyclylamide is used in combination with at least one azole.

In a preferred embodiment of the invention, at least one aryl and / or heterocyclylmide is used as the fungicide. With regard to suitable and preferred amides, reference is made to the above statements. In particular, boscalid is used as the amide fungicide. In an alternatively preferred embodiment of the invention, at least one azole is used as a fungicide. With regard to suitable and preferred azoles, reference is made to the above statements. Preference is given to using metconazole, prothioconazole or tebuconazole or their combination as azole fungicide. In particular, metconazole is used as the azole fungicide.

In an alternatively preferred embodiment of the invention, at least one strobilurin is used as a fungicide. With regard to suitable and preferred strobilurins, reference is made to the above statements. Azo-xystrobin or dimoxystrobin or their combination is preferably used as strobilurin fungicide. In particular, dimoxystrobin is used as the strobilurin fungicide.

In an alternatively preferred embodiment of the invention, at least one aryl or heterocyclylamide fungicide is used in combination with at least one azole fungicide. Preferred amide fungicide is boscalid. Preferred azole fungicide is metconazole.

In an alternative preferred embodiment of the invention, at least one aryl or heterocyclylamide fungicide is used in combination with at least one strobilurin fungicide. Preferred amide fungicide is boscalid. Preferred strobilurin fungicide is dimoxystrobin.

Particular preference is given to using at least one aryl or heterocyclylamide as fungicide, especially boscalid, optionally in combination with at least one azole fungicide, especially with metconazole, or optionally in combination with at least one strobilurin fungicide, especially with dimoxystrobin, or More preferably, it uses at least one azole fungicide, especially metconazole. In particular, at least one aryl or heterocyclylamide is used as the fungicide, especially boscalid, in combination with at least one azole fungicide, especially with metconazole.

When the at least one fungicide is used in combination with at least one growth regulator, the weight ratio of fungicide to growth regulator is preferably 15: 1000 to 1000: 15, more preferably 3:50 to 25: 7 and especially 6:50 to 15: 7.

The use according to the invention generally takes place in such a way that the oil plants or plant parts thereof or the seed of the oil plants are treated with these compounds. The treatment of oil plants or seeds takes place preferably so that the oil plant or plant parts thereof or the seed is brought into contact with at least one of the fungicides used according to the invention and optionally with at least one growth regulator. For this purpose, at least one fungicide is applied to the plant or to plant parts thereof or to the seed. If several fungicides used according to the invention are combined, they can be applied in a mixture or separately. In the separate application, the application of the individual active substances at the same time or - within a treatment sequence - staggered one after the other, where they in the successive application in a time interval of a few seconds or a few minutes to several weeks or even a few months, eg up to 10 months. Also, a single active substance can be applied several times, for example at a time interval of the individual applications of a few seconds or a few minutes to several weeks or even a few months, for example of up to 10 months. The same applies to the optional treatment with at least one growth regulator, ie the at least one fungicide and the at least one growth regulator can be administered in a mixture or separately and in the latter case simultaneously or sequentially. With successive application of the active ingredients, these can also be applied to different stages of development of the plants. Thus, for example, one active ingredient can be applied to the seed from which the plant is to grow and another or the same active ingredient to the plant or plant parts thereof at a developmental stage after emergence.

It goes without saying that the oil plants or parts thereof to be treated are living plants or plant parts on living plants.

The application dates, the number of applications and the application rates specifically used are to be adapted to the respective conditions and must be determined in each case by a person skilled in the art. In addition to the active substances used in each case, a distinction must be made in particular as to whether treatment is to be carried out on intact plants under field conditions or whether seed should be treated.

If a plant or a plant part is treated, the treatment is preferably carried out in the growth stage 1 to 6, more preferably 2 to 6, more preferably 3 to 6 and in particular 3 to 5 (according to BBCH macrostages, Federal Biological Research Center for Agriculture and Forestry; see www.bba.de/veroeff/bbch/bbch.htm).

In the most preferred fungicides used according to the invention, namely the at least one aryl or heterocyclylamide, especially boscalid, in combination with the at least one azole fungicide, especially with metconazole, it is preferred the plant or plant parts thereof with the at least one azole one or more times before flowering, preferably in the fall and / or spring, more preferably in the fall and in the spring, and to treat with the at least one aryl or Heterocyclylamid during flowering.

Autumn and spring are relative terms, which depend on the earth's hemisphere and the respective vegetation zone and plant and refer in the context of the present invention to those stages of development of the plant in which it would be in Central Europe at these seasons. Generally speaking, autumn is the season in which the oil plant is in the growth stage 01 to 39 and the spring before flowering the season in which the oil plant is in the growth stage 07 to 49 (according to extended BBCH scale; and forestry, see www.bba.de/veroeff/bbch/bbch.htm). The overlap of the growth phases depends on the weather in each year and on the individual plant species.

Particularly preferably, the oil plant or plant parts thereof is treated with the at least one azole once or several times, preferably once or twice, when the plant is in the growth stage 01 to 29 and then again one or more times, preferably on or twice, when the plant is in the growth stage 30 to 39; Subsequently, the oil plant or plant parts thereof with the at least one aryl or heterocyclylamide one or more times, preferably once or twice, treated when the plant is in the growth stage 50 to 69.

The active compounds can be used as such or in the form of their formulations or in the form of the application forms prepared by spraying, spraying, atomizing, dusting, scattering, pouring or pickling. The forms of application depend entirely on the intended use, v. a. according to the plant species and variety or the plant part and the stage of development of the plant to be applied to; In any case, they should ensure the finest possible distribution of the active ingredients used according to the invention and also of the auxiliaries.

The fungicides used according to the invention and the growth regulators optionally used are typically used as formulations, as are customary in the field of plant protection and storage protection.

Typical formulations are, for example, solutions, emulsions, suspensions, dispersions, pastes, dusts, scattering agents, powders and granules. The formulations are prepared in a known manner, for example by stretching the active ingredient with solvents and / or excipients, if desired using emulsifiers and dispersants. Suitable solvents / auxiliaries are essentially: water, aromatic solvents (eg Solvesso products, xylene), paraffins (eg petroleum fractions), alcohols (eg methanol, butanol, pentanol, benzyl alcohol), ketones (eg cyclohexanone, gamma Butyrolactone), pyrrolidones (NMP, NOP), acetates (glycol diacetate), glycols, dimethyl fatty acid amides, fatty acids and fatty acid esters. In principle, solvent mixtures can also be used.

Carriers such as ground natural minerals (e.g., kaolins, clays, talc, chalk) and ground synthetic minerals (e.g., fumed silica, silicates).

Surfactants such as alkali, alkaline earth, ammonium salts of aromatic sulfonic acids, e.g. Ligninsulfonic acid, phenolsulfonic acid, naphthalenesulfonic acid and dibutylnaphthalenesulfonic acid, and of fatty acids, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, furthermore condensation products of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol or nonylphenol, alkylphenyl polyglycol ethers, tributylphenyl polyglycol ethers, tristearylphenyl polyglycol ethers, alkylarylpolyether alcohols, isotridecyl alcohol, alcohol and fatty alcohol ethoxide condensates, ethoxylated castor oil, polyoxyethylene or polyoxypropylene alkyl ethers, ethoxylated polyoxypropylene, lauryl alcohol polyglycol. lether acetate, sorbitol esters, Ligninsulfitablaugen, methyl cellulose or siloxanes. Suitable siloxanes are, for example, polyether polymethylsiloxane copolymers, which are also referred to as "spreaders" or "penetrators".

Suitable inert formulation auxiliaries, in particular for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions, are essentially: mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, coal tar oils and oils of plant or animal origin, aliphatic, cyclic and aromatic Hydrocarbons, for example toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, alcohols, such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone and isophorone, strongly polar solvents, for example dimethyl sulfoxide, N-methylpyrrolidone or water , Powders, dispersants and dusts may be prepared by mixing or co-grinding the active substances with a solid carrier.

Granules, e.g. Coated, impregnated and homogeneous granules can be prepared by binding the active compounds to solid carriers.

Solid carriers are e.g. Mineral earths, such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulphate, magnesium oxide, ground plastics, fertilizers, e.g. Ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powders and other solid carriers.

The formulations generally contain the fungicides used according to the invention in a total amount of from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, based on the total weight of the formulation.

Products (formulations) for dilution in water are, for example, water-soluble concentrates (SL), dispersible concentrates (TLC), emulsifiable concentrates (EC), emulsions (EW, EO), suspensions (SC, OD, SE), water-dispersible and water-soluble granules (WG , SG) as well as water-dispersible and water-soluble powders (WP, SP). Products (formulations) for direct application include dusts (DP), granules (GR, FG, GG, MG) and ULV solutions (UL).

Aqueous application forms can be prepared from storage formulations, such as concentrated solutions, emulsion concentrates, suspensions, pastes, wettable powders (wettable powders, oil dispersions) or water-dispersible granules, by addition of water and applied, for example, by spraying.

To prepare emulsions, pastes or oil dispersions, the fungicides used according to the invention can be dissolved as such or in an oil or solvent and homogenized in water by means of wetting agents, tackifiers, dispersants or emulsifiers. But it can also be prepared from the active substance wetting, adhesion, dispersing or emulsifying and possibly solvent or oil concentrates, which are suitable for dilution with water. It goes without saying that the use forms contain the auxiliaries used in the storage formulations. The active substance concentrations in preparations diluted with water can be varied within larger ranges. In general, they are between 0.0001 and 10 wt .-%, preferably between 0.01 and 1 wt .-%.

The active substances may be oils of various types, wetting agents, safeners, adjuvants, other fungicides, insecticides, herbicides, bactericides or even foliar fertilizers, which are e.g. Contain trace elements and / or oligo elements, if necessary, only immediately before use (tank mix) are added. These agents can also be applied separately to the fungicides used according to the invention, wherein the separate application can take place before, simultaneously with or after the application of the fungicides. These agents can be added to the fungicides used according to the invention in a weight ratio of 1: 200 to 200: 1, preferably 1: 100 to 100: 1.

The combined use of the fungicides used according to the invention with further active ingredients customary in crop protection, e.g. with other fungicides, can be done either by using a mixture of these agents (e.g., a common formulation or a tank mix) as well as by the separate, simultaneous or successive application of the individual drugs.

When the fungicides used according to the invention are used in combination with at least one of the abovementioned agents, their use in combination with at least one different fungicide and / or at least one insecticide is particularly suitable.

The following list of fungicides, with which the fungicides used according to the invention can be used together, is intended to explain but not limit the possible combinations:

Acylalanines such as benalaxyl, metalaxyl, ofurace, oxadixyl, amine derivatives such as aldimorph, dodine, dodemorph, fenpropimorph, fenpropidin, guazatine, iminoctadine, spiroxamine, tridemorph,

Anilinopyrimidines such as pyrimethanil, mepanipyrim or cyprodinil,

Antibiotics such as cycloheximide, griseofulvin, kasugamycin, natamycin, polyoxin or streptomycin, dithiocarbamates such as Ferbam, Nabam, Maneb, Mancozeb, Metam, Metiram, Propecine, Polycarbamate, Thiram, Ziram, Zineb,

Heterocyclic compounds such as anilazine, cyazofamide, dazomet, dithianone, fenamidone, fenarimol, fuberidazole, isoprothiolane, nuarimol, probenazole, pro quinazide, pyrifenox, pyroquilon, quinoxyfen, silthiofam, thiabendazole, tricyclazole, triforine,

Copper fungicides such as Bordeaux broth, copper acetate, copper oxychloride, basic copper sulfate, nitrophenyl derivatives such as binapacryl, dinocap, dinobuton, nitrophthalic-isopropyl,

Phenylpyrroles such as fenpiclonil or fludioxonil,

• sulfur,

Other fungicides such as acibenzolar-S-methyl, carpropamide, chlorothalonil, cyfluhenamide, cymoxanil, diclomethine, diclocymet, diethofencarb, edifenphos, ethaboxam, fenhexamide, fentin acetate, fenoxanil, ferimzone, fluazinam, fosetyl, foseyl Aluminum, hexachlorobenzene, metrafenone, pencycuron, phthalide, tol-clofos-methyl, quintozene, zoxamide,

• cinnamic acid amides and analogues such as flumetover or flumorph.

The fungicides used according to the invention and the growth regulators optionally used are preferably applied to the oil plant or to parts thereof. It goes without saying that the treatment takes place on a living plant. Preference is given to applying to the aerial part of the plant.

However, seed treatment is also suitable for some fungicides.

In a preferred embodiment for field applications, i. Application to growing plants or plant parts thereof, using the fungicides used in the invention and the growth regulators optionally used in the form of an aqueous spray mixture. The application is preferably by spraying. It is applied either to the entire aboveground plant part or only to individual plant parts, such as flowers, fruits, leaves or individual shoots. The choice of the individual plant parts to be applied depends on the plant species and its stage of development. Preferably, it is applied to the entire above-ground plant part.

Per season, the fungicides used according to the invention are preferably applied 1 to 5 times, more preferably 1 to 3 times and especially 1 or 2 times. If treated repeatedly, at least the second, third, etc. treatment is usually a field application. With regard to the preferred type and frequency of application in the preferred use of at least one aryl or heterocyclylamide in combination with at least one azole, reference is made to the above statements. In the case of seeds, the fungicides used according to the invention are used in a formulation customary for this application.

In principle, all customary methods of seed treatment or seed dressing, such as, for example, dry pickling, moist pickling, wet pickling, slurry pickling or encrusting, can be used to treat the seed. Specifically, in the treatment, the seed is treated with the respective desired amount of seed dressing formulations either as such or after prior dilution with water in a suitable apparatus, for example a mixing device for solid or solid / liquid mixture partners up to even distribution of the agent on the seed mixes. Optionally, a drying process follows.

In general, the fungicides used according to the invention are used in the field application in an amount of 5 to 3000 g single active ingredient per ha per season, preferably 10 to 1000, particularly preferably 50 to 500 g single active ingredient per ha per season.

In general, the fungicides used according to the invention are used in the case of seed application in an amount of 0.01 g to 500 g, preferably 0.5 g to 200 g of single active substance per kg of seed.

The optionally used growth regulators are used in the field application in an amount of 10 to 1500 g single active ingredient per ha per season, preferably 25 to 650, more preferably 70 to 450 g single active ingredient per ha per season.

Per season, the growth regulators optionally used are preferably applied 1 to 4 times, more preferably 1 to 3 times and especially 1 or 2 times.

Another object of the present invention is a process for increasing the quality and optionally the quantity of oil plant products, comprising treating an oil plant or plant parts thereof or their seeds with at least one of the aforementioned fungicides, optionally in combination with at least one growth regulator, harvesting the Seeds of the oil plant at a time when their water content is not more than 15% by weight relative to the total weight of the seeds and the production of the oil plant products.

The increase in quality and, where appropriate, in the quantity of oil plant products is as defined above. With regard to suitable and preferred oil crops, oil crop products and fungicides and the amount and manner in which they are used, reference is made to the above.

The treatment of the oil plant or of plant parts thereof during the growth phase is preferably 1 to 6, more preferably 2 to 6, more preferably 3 to 6 and in particular 3 to 5 (according to BBCH macrostages, Federal Biological Research Center for Agriculture and Forestry, see www.bba .com / publ / BBCH / bbch.htm). The treatment of the oil plant preferably takes place at least partly during the flowering phase, i. at least one fungicide is applied during the flowering phase and optionally the same or a different fungicide is used during a different growing season. If several fungicides to be used according to the invention are combined, it is preferred to use a fungicide during the flowering phase and to add the other fungicide (s) before the flowering phase, e.g. in the spring and / or in the autumn before. For example, when amide fungicides are combined with azole fungicides, it is preferred that the amide fungicide (s) in the bloom phase and the azole fungicide (s) beforehand, e.g. to be applied in spring and / or autumn. For further details, reference is made to the above statements.

Harvesting occurs when the water content of the seeds is at most 15% by weight, e.g. 6 to 15% by weight, more preferably at most 14% by weight, e.g. 6 to 14% by weight, especially at most 12% by weight, e.g. 6 to 12% by weight, and especially at most 9% by weight, e.g. 6 to 9 wt .-%, based on the total weight of the seeds, is. The optimal water content depends on the individual oil plant. For example, in the case of soybean and maize, it tends to be in the higher limit, e.g. at most 15% by weight, e.g. 10 to 15% by weight and especially at most 14% by weight, e.g. at 10-14% by weight, in sunflower in the middle range, e.g. at most 13% by weight, e.g. 9 to 13% by weight and especially at most 12% by weight, e.g. at 9 to 12% by weight, in the case of rapeseed in the lower range, e.g. at most 11% by weight, e.g. 7 to 1 1% by weight and especially at most 9% by weight, e.g. at 7 to 9% by weight, and in flax at an even lower range, e.g. at most 9% by weight, e.g. 6 to 9% by weight and especially at most 7% by weight, e.g. at 6 to 7 wt .-%.

The water content can be determined by customary analysis methods, for example by determining the weight loss during drying under defined conditions (eg 100 ^° C. over a defined period of time) or by determining the electrical conductivity under defined conditions (especially temperature), eg with a grain Moisture meter Pfeuffer HE Lite from Pfeuffer GmbH, Germany.

The extraction of oil from the oil-supplying parts of the plant, namely from the seeds, fruits and / or nuts of the oil plant, is carried out according to the methods customary for the respective plant or plant product, for example by pressing and / or extraction. The respective pre-treatment or post-treatment measures required for the individual plants or their plant products are sufficiently known to the person skilled in the art.

When recovering the oil in the pressing process falls as a residue of the so-called press cake. This can be used further, e.g. as feed or as fuel.

The process according to the invention preferably leads to a lowering of the phosphorus content of the products of the treated plants, in particular of the oil obtained from the oil plants and / or the reaction products thereof, for example its C 1 -C ₄ -alkyl ester.

Alternatively or additionally, the process according to the invention leads to a lowering of the alkali and / or alkaline earth metal content, in particular of the alkaline earth metal content and especially of the calcium and magnesium content of the products of the treated plants, in particular of the oil obtained from the oil plants and / or the reaction products thereof, e.g. its Ci-C4-alkyl ester.

Alternatively or additionally, the method according to the invention results in a reduction of the acid content (measured as acid number) of the products of the treated plants, in particular of the oil obtained from the oil plants and optionally the reaction products thereof, e.g. its Ci-C4-alkyl ester.

Alternatively or additionally, the method according to the invention leads to a reduction in the iodine value of the products of the treated plants, in particular of the oil obtained from the oil plants and / or the reaction products thereof, for example its C 1 -C ₄ -alkyl ester.

Alternatively or additionally, the process according to the invention leads to an increase in the oxidation stability of the products of the treated plants, in particular of the oil obtained from the oil plants and optionally the reaction products thereof, for example its C 1 -C ₄ -alkyl ester. Alternatively or additionally, the process according to the invention leads to a reduction in the total contamination of the products of the treated plants, in particular of the oil obtained from the oil plants and optionally the reaction products thereof, for example its C 1 -C 4 -alkyl ester.

Alternatively or additionally, the method according to the invention leads to a lowering of the kinematic viscosity of the products of the treated plants, in particular of the oil obtained from the oil plants and optionally the reaction products thereof, e.g. its Ci-C4-alkyl ester.

Alternatively or additionally, the process according to the invention results in a lowering of the sulfur content of the products of the treated plants, in particular of the oil obtained from the oil plants and optionally the reaction products thereof, e.g. its Ci-C4-alkyl ester.

Alternatively or additionally, the method according to the invention leads to an increase in the flashpoint of the products of the treated plants, in particular of the oil obtained from the oil plants and optionally the reaction products thereof, for example its C 1 -C ₄ -alkyl ester.

Alternatively or additionally, the method according to the invention leads to an increase in the calorific value of the products of the treated plants, in particular of the oil obtained from the oil plants and optionally the reaction products thereof, e.g. its Ci-C4-alkyl ester.

Alternatively or additionally, the process according to the invention leads to a lowering of the coke residue of the products of the treated plants, in particular of the oil obtained from the oil plants and optionally the reaction products thereof, e.g. its Ci-C4-alkyl ester.

Alternatively or additionally, the process according to the invention leads to an increase in the cetane number of the products of the treated plants, in particular the oil obtained from the oil plants and optionally the reaction products thereof, e.g. its Ci-C4-alkyl ester.

Alternatively or additionally, the inventive method leads to a reduction of the nitrogen content of the products of the treated plants, in particular of the oil obtained from the oil plants and, if appropriate, the reaction products thereof, for example its C 1 -C 4 -alkyl ester.

Alternatively or additionally, the process according to the invention leads to a lowering of the chlorine content of the products of the treated plants, in particular of the oil obtained from the oil plants and optionally the reaction products thereof, e.g. its Ci-C4-alkyl ester.

Alternatively or additionally, the method according to the invention leads to a lowering of the content of tin, zinc, silicon and / or boron of the products of the treated plants, in particular of the oil obtained from the oil plants and optionally the reaction products thereof, e.g. its Ci-C4-alkyl ester.

The process according to the invention particularly preferably leads to an improvement in the properties of the products of the treated plants, in particular of the oil plants, listed under (i) to (xi), more preferably (i) to (viii) and especially (i) to (vii) recovered oil and optionally the reaction products thereof, eg its Ci-C4-alkyl ester.

The process according to the invention particularly preferably leads to a lowering of the phosphorus content and / or the alkali and / or alkaline earth metal content and / or the acid content, in particular to a lowering of the phosphorus content and / or the acid content of the products of the treated plants, in particular of those obtained from the oil plants Oil and / or the reaction products thereof, eg its Ci-C4-alkyl ester. Accordingly, the process according to the invention particularly preferably serves for the production of oil plant products, in particular of vegetable oil and / or reaction products thereof, e.g. its Ci-C4-alkyl esters, with a reduced phosphorus content and / or alkali and / or alkaline earth metal content and / or acid content and in particular with a reduced phosphorus content and / or acid content.

The acidity of the oil plant products, especially the oil and optionally the reaction products thereof can be determined, for example, according to DIN EN 14104 (as acid number). The oxidation stability can be measured according to DIN EN 14112. The determination of the phosphorus content can be carried out according to DIN EN 14107 and the alkali (especially Na and K) and alkaline earth metal content (calcium and magnesium) according to DIN EN 14538. The determination of the iodine number can be done according to EN 141 11. The total contamination can be measured according to EN 12662, for example. The kinematic viscosity can be determined according to EN ISO 3104, for example. The flash point may be in accordance with EN ISO 2719, the lower calorific value according to DIN 51900-1 and -3, the coke residue according to Conradson according to EN ISO 10370 and the cetane number according to DIN 51773. The sulfur content can be determined in accordance with EN ISO 20884 and that of the chlorine content in accordance with DIN 51577-3. Tin, zinc and silicon contents can be measured according to DIN 51396-1 and the boron content according to DIN 51443-2.

The terms "phosphorus content", "alkali metal content", "alkaline earth metal content", "acid content / acid number", "iodine number", "oxidation stability", "total contamination", "kinematic viscosity", "flash point", "used in the context of the present invention lower calorific value "," coke residue "," cetane number "," sulfur content "," chlorine content "and" zinc, tin, silicon and boron content "are preferably defined as in the corresponding standards for determining their size.

The oil obtained from the fruits and / or seeds of oil plants treated according to the invention may be used in the food industry, e.g. as edible oil or for the production of margarine, in the cosmetics sector, e.g. as a carrier, as a lubricant or for energy, i. used as fuel or fuel. If used in the food industry, the resulting oil may need to be subjected to further refining steps to remove any unwanted flavors, odors, colors, inedible components, and the like.

Preferably, the oil is used as fuel or fuel.

The oil according to the invention is characterized, inter alia, by a reduced acid content and / or an improved oxidation stability and / or a reduced phosphorus content and / or a reduced content of alkali metal and especially alkaline earth metal compounds and / or a reduced content of suspended particles and other interfering components in comparison to oils derived from untreated oil plants. Additionally or alternatively, the oil according to the invention is characterized by at least one property listed under (iv), (v) and (vii) to (xv), for example by a lower iodine number, lower kinematic viscosity and / or lower total contamination etc. (in comparison to oils obtained from plants not treated according to the invention).

The reaction products of the oil are preferably its transesterification products with C 1 -C 4 -alcohols, ie the C 1 -C 4 -alkyl esters of the fatty acids on which the oils are based. Particular preference is given to the transesterification products of the oil with methanol or ethanol and in particular with methanol, ie, the methyl or ethyl esters and especially the methyl esters of the fatty acids underlying the oils. The C 1 -C 4 -alkyl esters are obtainable by transesterifying the vegetable oil with a C 1 -C 4 -alcohol, usually in the presence of a catalyst (generally a base). The fatty acid triglycerides of the oil are converted into the C 1 -C 4 -alkyl esters of the corresponding fatty acids. These esters are referred to in the context of the present invention as Ci-C4-alkyl ester of vegetable oil.

The reaction products of the oil, and in particular its transesterification products with C 1 -C 4 -alcohols, are primarily for use for energy production, i. as fuel or fuel.

The reaction products of the oil and especially the Ci-C4-alkyl esters of the oil are characterized by the properties mentioned in the oil.

When pressing the fruits and / or seeds of oil plants is obtained as a residue a press cake, which is like the fruits and seeds by a reduced content of phosphorus and / or alkali metal and especially alkaline earth metal compounds and / or a reduced acidity and in particular by a characterized reduced phosphorus content and / or acidity. This can be used both in the feed sector and for direct energy production, i. be used as a fuel, especially in combustion plants, with a use for energy production is preferred.

Particularly preferred are the oil crop products among seeds, vegetable oils and their reaction products, e.g. the transesterification products with Ci-C4-alcohols, selected. In particular, the oil plant products are among oils and their reaction products, e.g. the transesterification products with Ci-C4-alcohols, selected.

By treating oilseeds or the seeds from which they grow with the previously specified fungicides, optionally in combination with growth regulators, the development of the plants is made more homogeneous. Thus, for example, the flowering takes place within the individual plant stages (ie, the areas within a plant (one and the same plant) which are at different heights) at the same time, ie, in a much narrower time interval, as does the pod development and, in particular, the maturation of the plants fruits / seeds. The same applies to the development in plants with parts of plants that extend to a larger diameter around the stem than the center, such as the seeds in the sunflower. The increase in the quality of oilseed products, resulting, for example, in a reduction in the phosphorus content, and / or the alkali metal content and / or alkaline earth metal content and / or the acid content and / or in the increase of the oxidation stability, etc. expresses, is probably due at least partially to this more homogeneous development of the plant. This, and especially while maintaining a favorable harvest time, gives seeds / fruits of oil plants, which have an optimal quality in terms of the upper criteria. At the same time, the quantity is also optimized, as fewer fruit / seeds are immature or overripe due to the simultaneous ripening of the fruit / seeds at the time of harvesting, resulting in fewer crop losses.

Claims

claims

1. Use of at least one fungicide which is selected from aryl and heterocyclylamides, carbamates, dicarboximides, azoles, strobilurins and morpholines, optionally in combination with at least one growth regulator, for achieving a temporally more uniform course of the phenological development of oil plants.

2. Use according to claim 1, for achieving a more uniform maturation of the seeds of oil crops.

3. Use according to one of the preceding claims, wherein the oil plants are selected from oilseed rape, turnip rape, mustard, oil radish, camelina, Ölrauke, Krambe, sunflower, safflower, thistle, marigold, soybean, lupine, flax, hemp, pumpkin, poppy , Corn, oil palm and peanut.

4. Use according to claim 3, wherein the oil plants are selected from rape and turnip rape.

5. Use according to one of the preceding claims, wherein the aryl and Heterocyclylamide are selected from compounds of the formula I.

A-CO-NH-MQR ¹ where

A is an aryl group or an aromatic or non-aromatic 5- or 6-membered heterocycle containing 1 to 3 heteroatoms or heteroatom-containing groups as ring members which are selected from O, S, N and NR ² , where R ² is hydrogen or C 1 -C ₈ -alkyl, where the aryl group or the heterocycle optionally have 1, 2 or 3 substituents which are selected independently from among halogen, C 1 -C ₈ -alkyl, C 1 -C ₈ -haloalkyl, C 1 -C ₈ alkoxy, _{Ci-C8-haloalkoxy,} Ci-C ₈ - alkylthio, _{Ci-C8-alkylsulfinyl} and Ci-C ₈ alkylsulfonyl;

M is a thienyl ring or a phenyl ring, wherein the thienyl and the phenyl ring can carry 1, 2 or 3 halogen atoms and wherein the phenyl ring is optionally condensed with a saturated 5-membered ring which is optionally substituted by 1, 2 or 3 Ci-C ₈ -alkyl substituted and / or optionally a heteroatom selected from O and S, as a ring member; Q kylen ₆ Al is a bond, Ci-C, C2-C6-alkenylene, C2-C6 alkynylene, C3-C6 cycloalkylene, C ₃ -C ₆ -cycloalkenylene, -O-Ci-C ₆ alkylene, - OC ₂ -C ₆ -alkenylene, -OC ₂ -C ₆ -alkynylene, -O-Cs-Ce-cycloalkylene, -O-Cs-Ce-cycloalkenylene, -S-Ci-C ₆ -alkylene, -SC ₂ -C ₆ alkenylene, -S-C ₂ -C ₆ alkynylene, -SC ₃ -C ₆ - cycloalkylene, -S-Cs-Ce-cycloalkenylene, _{-SO-Ci-C6-alkylene,} -SO-C ₂ -C ₆ - Alkenylene, -SO-C ₂ -C ₆ alkynylene, -SO-Cs-Ce-cycloalkylene, -SO-C ₃ -C ₆ -cycloalkenylene, -SO ₂ -Ci -C ₆ alkylene, -SO ₂ -C ₂ -C ₆ alkenylene, -SO ₂ -C ₂ -C ₆ - alkynylene, -SO ₂ -C 3 -C ₆ cycloalkylene, -SO ₂ -C ₃ -C ₆ -cycloalkenylene, O, S, SO or SO ₂ stands;

wherein the aliphatic and cycloaliphatic radicals in Q may be partially or completely halogenated and / or the cycloaliphatic radicals may be substituted by 1, 2 or 3 C 1 -C -alkyl radicals;

R ^{1 represents} hydrogen, halogen, C 3 -C ₆ -cycloalkyl or phenyl, where the cycloalkyl radical can carry a methyl group and where phenyl is substituted by 1 to 5 halogen atoms and / or by 1, 2 or 3 substituents which are selected independently from among Ce-Al kyl, d-Cs-haloalkyl, d-Cs-alkoxy, d-Cs-haloalkoxy, Ci-C ₈ alkylthio and Ci-C ₈ haloalkylthio, may be substituted.

6. Use according to claim 5, wherein the amide of the formula I is selected from anilides of the formula 1.1

wherein A is a group of the formula A1 to A8

(A1) (A2) (A3)

(A7) (A8)

stands in which

X is CH ₂ , S, SO or SO ₂ ;

R ^{3 is} CH ₃ , CHF ₂ , CF ₃ , Cl, Br or I;

R ^{4 is} CF ₃ or Cl;

R ^{5 is} hydrogen or CH ₃ ;

R ^{6 is} CH ₃ , CHF ₂ , CF ₃ or Cl;

R ^{7 is} hydrogen, CH ₃ or Cl;

R ^{8 is} CH ₃ , CHF ₂ or CF ₃ ;

R ^{9 is} hydrogen, CH ₃ , CHF ₂ , CF ₃ or Cl; and

R ^{10 is} C 1 -C ₄ -alkyl, C 1 -C ₄ -alkoxy, C 1 -C ₄ -alkylthio or halogen.

7. Use according to claim 6, wherein A is the group A2, wherein R ^{4 is} halogen and wherein R ^{10 is} halogen.

8. Use according to claim 7, wherein the amide I is selected from anilides of the formulas 1.1.1 and 1.1.2

(1.1 .1) (1.1 .2)

9. Use according to one of the preceding claims, wherein the azoles are selected from difenoconazole, flusilazole, metconazole, paclobutrazole, prothio-conazole and tebuconazole.

Use according to any one of the preceding claims, wherein the strobilurins are selected from azoxystrobin, dimoxystrobin and pyraclostrobin.

Use according to any one of the preceding claims, wherein the morpholine fungicide is dimethomorph.

12. Use according to one of the preceding claims, of at least one aryl or Heterocyclylamid in combination with at least one azole.

13. Use according to claim 12, wherein as aryl or heterocyclylamide boscalid and azol used as metconazole.

14. Use according to one of the preceding claims, wherein the growth regulators are selected from

(a) acylcyclohexanediones of the formula (IV)

wherein

R ^{A is} H or Ci-Cio-alkyl and R ^B is C ₁ -C 10 -alkyl or C ₃ -C 10 -cycloalkyl

or salts thereof; and

(b) Quaternary ammonium compounds of the formula (V)

wherein

R ^c and R ^D independently of one another are ^C 1 -C 10 -alkyl which is optionally substituted by at least one halogen atom, or C 3 -C 10 -alkyl

Cycloalkyl; or

R ^c and R ^D together represent a bridging unit - (CH 2) _n -,

- (CH ₂ ) 2-O- (CH ₂ ) 2- or - (CH ₂ ) -CH = CH- (CH ₂ ) -NH-,

wherein n is 4 or 5, and

Z- represents a counteranion selected from halide ions,

Sulfate ions, Ci-Cio-Alkylsulfonationen, borate ions, carbonate ions and mixtures thereof.

15. Use according to claim 14, wherein as compounds of formula (IV) the alkali metal or alkaline earth metal salts thereof, wherein R ^{A is} H, is used.

16. Use according to claim 15, wherein R ^{B is} ethyl.

17. Use according to one of claims 15 or 16, wherein it is the calcium salt.

18. Use according to claim 14, wherein in compounds of formula (IV) R ^{A is} ethyl and R ^{B is} cyclopropyl.

19. Use according to claim 14, wherein in compounds of formula (V) R ^{c is} methyl and R ^{D is} 2-chloroethyl.

20. Use according to claim 14, wherein in compounds of formula (V) R ^c and R ^D together form a bridging unit - (CHb) S-.

Use according to any one of claims 14 or 18 to 20, wherein in compounds of formula (V) Z - represents chloride.

22. A method for achieving a more uniform temporal course of the phenological development of oil plants, wherein the oil plant or plant parts thereof or their seed with at least one fungicide, optionally in combination with at least one growth regulator, as defined in any one of claims 1 to 21 treated.

23. The method of claim 22, wherein treating the oil plant or plant parts thereof with at least one aryl or Heterocyclylamid in combination with at least one azole.

24. The method of claim 23, wherein treating the oil plant or plant parts thereof with the at least one azole one or more times before flowering and with the at least one aryl or Heterocyclylamid during flowering.

25. A process for increasing the quality and, where appropriate, the quantity of oil plant products, comprising treating an oil plant or plant parts thereof or their seeds with at least one fungicide, optionally in combination with at least one growth regulator, as defined in any one of claims 1 to 21, the seeds of the oilseed crop are harvested when their water content is at most 15% by weight, relative to the total weight of the seeds, and the oilseed product is obtained, the increase in quality being selected according to the following criteria:

(i) reducing the phosphorus content of at least one oilseed product;

(ii) reducing the alkali and / or alkaline earth content of at least one oil plant product;

(iii) increasing the oxidation stability of at least one oil plant product; (iv) reducing the overall pollution of at least one oilseed product;

(v) lowering the iodine value of at least one oil plant product; (vi) lowering the acid number of at least one oil plant product; (vii) reducing the kinematic viscosity of at least one oil crop certificate;

(viii) reducing the sulfur content of at least one oil crop product; (ix) increasing the flashpoint of at least one oil plant product;

(x) increasing the net calorific value of at least one oilseed product;

(xi) reducing the coke residue of at least one oilseed product;

(xii) increasing the cetane number of at least one oil plant product;

(xiii) reducing the nitrogen content of at least one oil crop product;

(xiv) reducing the chlorine content of at least one oilseed product; and

(xv) reducing the content of tin, zinc, silicon and / or boron of at least one oil crop product.

A method according to claim 25, wherein the oil plant products are selected from among the fruits, seeds, press cake, oil and reaction products of the oil derived from the oil plants.

27. Process according to claim 26, wherein the reaction products of the oil are the transesterification products of the oil with C 1 -C 4 -alcohols.

A method according to any one of claims 25 to 27, wherein the oil crop products are selected from oil obtained from the oil crops and reaction products thereof.

29. The method according to any one of claims 25 to 28, wherein the oil plants are selected from oilseed rape, turnip rape, mustard, oil radish, camelina, Ölrauke, Krambe, sunflower, safflower, thistle, marigold, soybean, lupine, flax, hemp, Ölkür- , Poppy, corn, oil palm and peanut.

30. The method of claim 29, wherein the oil plants are selected from rape, turnip rape, sunflower and corn.

31. The method of claim 30, wherein the oil plants are selected from rape and turnip rape.

32. The method according to any one of claims 25 to 31, wherein the seeds of the oil crop are harvested when their water content is 5 to 15 wt .-%, based on the total weight of the seeds.

33. The method of claim 31, wherein the seeds of the rapeseed or Rübsenpflanze harvested when their water content is at most 10 wt .-%, preferably 7 to 9 wt .-%, based on the total weight of the seeds.