USE OF ACYLCYANAMIDES OR THEIR SALTS TO REGULATE PLANT GROWTH

Description

[0001] The present invention relates to the use of acylcyanamides or their salts as active ingredients of plant growth regulators, in particular for breaking the dormancy of fruit trees.

[0002] Plant growth regulators are active substances that specifically influence the growth, development, and metabolic processes of crops and cultivated plants, even when applied in minute doses. The term "plant growth regulator" encompasses both natural phytohormones and synthetic substances. Plant growth regulators are used to reduce or prevent the negative effects of numerous environmental factors in agricultural plant production, or to enhance their positive effects. The use of plant growth regulators can thus increase the yield potential of crops and cultivated plants, better utilize site factors, and ensure the effectiveness of intensification measures.

[0003] WO 2014 / 122066 A1 describes substituted aminoazoles as plant growth regulators. DE 40 04 379 A1 describes the use of alkaline earth metal salts of acylcyanamides as catalysts for the ethoxylation or propoxylation of compounds with active hydrogen atoms. WO 87 / 04348 describes acylated cyanamide compounds. DE 30 31 636 A1 describes the use of acylcyanamides as corrosion inhibitors. DE 1 907 193 describes acylcyanamides with biological, particularly herbicidal, activity.

[0004] Dormancy is a term for a resting period in the development and life cycle of plants, which can extend to buds and seeds and is characterized by the plant's failure to grow. Dormancy can be lifted or broken by light, temperature, or humidity. The so-called breaking of dormancy is induced, for example, in some seeds by species-specific cold periods ("stratification"). Similarly, bud dormancy is also ended by the influence of cold or frost, with changes in the concentration of the phytohormones abscisic acid, auxins, and gibberellins being observed in both cases. These natural rest periods are important from a plant physiological perspective, since premature budding in subsequent cold periods can lead to freezing and eventual death of newly formed plant parts.

[0005] Dormancy breaking, especially bud dormancy, can also be induced by plant growth regulators applied externally to the plants. Cyanamide, for example, has been known for some time as an active ingredient for breaking dormancy, especially in dessert fruit. Corresponding applications have been described, for example, in DE 3150404 and ZA 8302332. Further descriptions of the use of cyanamide-containing spray mixtures for dormancy breaking can be found, for example, in: Table grapes: Y. Shulman et. al., Scientia Horticulturae (1983), 19, 97, P. Spiegel-Roy et. al., HortScience (1987), 22, 208, Kiwi fruit: CCNee, New Zealand Journal of Crop and Horticultural Science (1991), 19, 419, Peach: JH Siller-Cepeda, HortScience (1992), 27, 874.

[0006] Artificial dormancy breaking, induced by the application of suitable active ingredients, is particularly economically valuable for postponing the harvest to an earlier time than the natural one, as this allows higher prices to be achieved for the fruit. For the cultivation of plants (e.g. grapes or cherries) in tropical regions, artificial dormancy breaking and thus the deliberate and calculated triggering of buds is indispensable, as these plants would naturally sprout hardly at all and only very unevenly in a tropical environment. In this respect, treatment with dormancy-breaking agents is indispensable for growing table grapes or cherries in tropical mountain regions, for example, and thus supplying the world market outside of the temperate latitude season in the northern or southern hemisphere.

[0007] Cyanamide for use as a dormancy-breaking spray is typically marketed as an aqueous solution, e.g., with a 50% cyanamide content and possibly other additives such as stabilizers, dyes, or surfactants. Alternatively, DE 102014003082 A1 describes an organic oil-based concentrate based on cyanamide, which exhibits an improved dormancy-breaking effect when diluted with water.

[0008] In addition to its desired dormancy-breaking effect on plants, cyanamide unfortunately also has a variety of physiological effects on animals and humans. Cyanamide is classified as highly corrosive (skin-damaging), acutely toxic, and teratogenic. Further studies have shown that special occupational safety measures must be observed when using cyanamide or cyanamide-containing solutions in agriculture.

[0009] Cyanamide is also a polymerizable substance that can only be transported and stored under special precautions (see K.-D. Wehrstedt et al., Journal of Hazardous Materials 170 (2009) 829-835). Concentrates used to produce a cyanamide-containing spray mixture are subject to degradation or dimerization, forming cyanoguanidine, even at normal storage temperatures, so their effectiveness is limited.

[0010] The present invention is therefore based on the object of providing an agricultural agent for regulating plant growth that is largely safe for the user and that can be classified as safe due to its ingredients and assessed as efficient in terms of its effect.

[0011] These objects are achieved by a use according to claim 1, a concentrate according to claim 7 and a method according to claim 15. Preferred embodiments of the invention are specified in the subclaims, which can optionally be combined with one another.

[0012] Thus, according to a first embodiment, the use of at least one compound from the group of acylcyanamides or a salt thereof according to formula (I) or formula (II) for regulating the generative growth of plants, in particular the generative growth of useful and cultivated plants, preferably the generative growth of fruit trees, or for breaking the dormancy of fruit trees is the subject of the present invention, wherein for formula (I) and formula (II) where for the radicals R 1< , R 2< , R 3< , R 4< , R 5< and the cations M 1< , M 2< independently of each other: R 1< = hydrogen, C 1 - to C 20 -alkyl, C 3 - to C 12 -cycloalkyl, C 2 - to C 20 -alkenyl, C 1 - to C 20 -alkoxy, aryl, alkylaryl or arylalkyl, or a radical Q, where Q = C 1 - to C 20 -alkyl, C 3 - to C 12 -cycloalkyl, C 2 - to C 20 -alkenyl, C 1 - to C 20 -alkoxy, aryl, alkylaryl or arylalkyl, each substituted by a radical of the formula (III) or formula (IV) M 1< , M 2< = independently of one another Li, Na, K, ½Ca, ½Mg or NR 2< R 3< R 4< R 5< , R 2< , R 3< , R 4< , R 5< = independently of one another hydrogen or C 1 - to C 20 -alkyl.

[0013] According to the present invention, the radical R 1< can be hydrogen, C 1 to C 20 alkyl, C 3 to C 12 cycloalkyl, C 2 to C 20 alkenyl, C 1 to C 20 alkoxy, aryl, alkylaryl, arylalkyl or a radical Q, where Q is a radical C 1 to C 20 alkyl, C 3 to C 12 cycloalkyl, C 2 to C 20 alkenyl, C 1 to C 20 alkoxy, aryl, alkylaryl or arylalkyl, which in turn is substituted by a radical of the formula (III) or formula (IV).

[0014] In the context of the present invention, C 1 - to C 20 -alkyl is to be understood as meaning a saturated, linear or branched, aliphatic radical having a chain length of 1 to 20 carbon atoms, in particular 1 to 8 carbon atoms, in particular an alkyl radical which has the general formula C n H 2n+1, where n = an integer from 1 to 20, preferably an integer from 1 to 12 and in particular an integer from 1 to 8. It is preferably provided that C 1 - to C 20 -alkyl means in particular methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, 2-ethylpropyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl or n-dodecyl.

[0015] According to the present invention, C 1 - to C 20 -alkyl particularly preferably means methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, or n-hexyl. Very particularly preferably, C 1 - to C 20 -alkyl according to the present invention means methyl, ethyl, n-propyl, n-butyl, n-pentyl, or n-hexyl.

[0016] In the context of the present invention, C 3 - to C 12 -cycloalkyl is further understood to mean a saturated, monocyclic or bicyclic aliphatic radical having 3 to 12 carbon atoms, in particular a cycloalkyl radical having the general formula C n H 2n-1 with n = an integer from 3 to 12. It is preferably provided that C 3 - to C 12 -cycloalkyl means in particular cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl, where these cycloalkyl radicals in turn can preferably be mono- or polysubstituted by alkyl.

[0017] According to the present invention, C 3 to C 12 cycloalkyl particularly preferably means cyclopentyl or cyclohexyl.

[0018] Furthermore, in the context of the present invention, alkanediyl is to be understood as meaning a saturated, linear or branched, aliphatic radical which has two bonding sites and in particular a chain length of 1 to 20 carbon atoms (C 1 -C 20 -alkanediyl), preferably of 1 to 12 carbon atoms (C 1 -C 12 -alkanediyl), in particular of 1 to 6 carbon atoms (C 1 -C 6 -alkanediyl), and which in particular has the general formula C n H 2n, where n = an integer from 1 to 12, in particular an integer from 1 to 6.

[0019] According to the present invention, alkanediyl particularly preferably means methanediyl, ethane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, propane-1,5-diyl or hexane-1,6-diyl.

[0020] Furthermore, in the context of the present invention, C 2 - to C 20 -alkenyl is to be understood as meaning an unsaturated, linear or branched, aliphatic radical with a chain length of 2 to 20 carbon atoms with one, two, three or four double bonds, which, depending in particular on the number of double bonds, has the general formula: one double bond, C n H 2n-1 with n = an integer from 2 to 20, two double bonds: C n H 2n-3 with n = an integer from 4 to 20, three double bonds C n H 2n-5 with n = an integer from 6 to 20 or four double bonds C n H 2n-7 with n = an integer from 8 to 20.It is preferably provided that C 2 - to C 20 -alkenyl is in particular ethenyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, butadienyl, pentadienyl, hexadienyl, heptadienyl, octadienyl, nonadienyl, decadienyl, hexarienyl, heptatrienyl, octatrienyl, nonatrienyl or decatrienyl, where these alkenyl radicals can furthermore preferably be unbranched or themselves mono- or polyalkyl-substituted.

[0021] According to the present invention, C 2 - to C 20 -alkenyl particularly preferably denotes heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, or octadecenyl. Very particularly preferably, C 2 - to C 20 -alkenyl denotes tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, or octadecenyl.

[0022] According to the present invention, C 1 -C 20 -alkoxy means a radical of the formula -O-alkyl, where the bonding site is located on the oxygen, and where alkyl is a C 1 -C 20 -alkyl radical as defined above. Preferably, the radical R 1 or Q is C 1 -C 12 -alkoxy, and more preferably C 1 -C 6 -alkoxy.

[0023] According to the present invention, C 1 - to C 20 -alkoxy particularly preferably denotes methoxy, ethoxy, n-propoxy, n-butoxy, or n-pentoxy. Most preferably, C 1 - to C 20 -alkyl according to the present invention denotes methoxy or ethoxy.

[0024] According to the present invention, aryl means an aromatic radical, in particular an aromatic radical having 6 to 20 carbon atoms, preferably having 6 to 10 carbon atoms, particularly preferably having 6 carbon atoms, which may be monocyclic, bicyclic, or polycyclic. Thus, according to the present invention, aryl may in particular mean phenyl, naphthyl, anthryl, phenantryl, pyrenyl, or perylenyl.

[0025] According to the present invention, aryl particularly preferably means phenyl.

[0026] According to the present invention, arylalkyl means an alkyl radical as defined above, which is substituted by an aryl radical as defined above, wherein the bonding site of the arylalkyl radical is located on the alkyl radical. Thus, according to the present invention, arylalkyl can in particular mean benzyl, 1-phenylethyl, or 1-methyl-1-phenylethyl.

[0027] According to the present invention, arylalkyl particularly preferably means benzyl.

[0028] According to the present invention, alkylaryl means an aryl radical of the meaning given above, which in turn is mono- or polysubstituted by an alkyl radical of the meaning given above, wherein the bonding site of the alkylaryl radical is located on the aryl radical.

[0029] Thus, according to the present invention, alkylaryl may in particular mean tolyl, xylyl, pseudocumyl or mesityl.

[0030] According to the present invention, alkylaryl particularly preferably means tolyl.

[0031] Surprisingly, it has been shown that acylcyanamides according to the invention or their salts according to formula (I) or formula (II) have an effect as plant growth regulators. This fact is all the more surprising given that these substances have been known as such for some time (cf. DE 32022013). However, to date, these acylcyanamides have only been attributed an effect as surfactants (cf. DE 708428) or as accelerators for anaerobic-curing adhesives (DE 3003437). No effect in the living plant is known. It is known that cyanamide itself is rapidly and completely metabolized to acetylcyanamide in humans and other vertebrates, thus detoxifying them (cf. FN Shirota et al., Drug Metabolism and Disposition (1984), 12, 337, and B. Mertschenk et al., Archives of Toxicology (1991), 65, 268). Acetylcyanamide is excreted from the human body via urine and can thus be quantified (cf. DE 3827449).Without being bound by theory, acylcyanamides must therefore have a different effect in plants than the detoxification mechanism in vertebrates. The fact that acylcyanamides according to the invention, especially acetylcyanamide, are not also "detoxified" in the plant and are thus ineffective, but rather exhibit dormancy-breaking effects, represents a completely surprising effect and the very essence of the invention.

[0032] A dormancy-breaking effect occurs when bud break and / or flowering of plants occurs earlier than the natural bud break and flowering of the plants. Thus, dormancy breaking regulates the generative growth of the plants.

[0033] It is desirable that the plants, particularly crops and cultivated plants or fruit trees, fully sprout and flower within a relatively short period of time, so that the further development phases of the treated plants are predictable. Such a dormancy-breaking effect was observed according to the invention with acylcyanamides of formula (I) or formula (II) (see examples).

[0034] Thus, by means of the inventive use of acylcyanamides or salts thereof according to formula (I) or according to formula (II), the generative growth of plants, in particular the generative growth of useful and cultivated plants, preferably the generative growth of fruit trees, can be regulated, or the dormancy of fruit trees can be broken.

[0035] In addition, acylcyanamides of the present invention have a positive property for use in agriculture. Compared to cyanamide, these compounds are storage-stable and largely soluble in liquids. It has also been shown that, unlike cyanamide, these acylcyanamides are not subject to degradation and / or dimerization in aqueous solutions.

[0036] Acylcyanamides of formula (I) according to the invention are weak NH acids, so they can form stable salts of formula (II) with bases. These salts have a neutral pH, are physiologically well tolerated, are storage-stable, and surprisingly are active as dormancy-breaking agents.

[0037] Acylcyanamides and their salts according to formula (I) or formula (II) are therefore ideally suited to replace cyanamide in those areas of application in which cyanamide cannot or should not be used due to its toxicological or other properties.

[0038] According to the present invention, acylcyanamides or salts thereof according to formula (I) or according to formula (II) can be used, the radical R 1< of which represents a radical from the group consisting of hydrogen, C 1 - to C 20 -alkyl, C 3 - to C 12 -cycloalkyl, C 2 - to C 20 -alkenyl, C 1 - to C 20 -alkoxy, aryl, alkylaryl or arylalkyl, or a radical Q, where Q represents a radical from the group consisting of C 1 - to C 20 -alkyl, C 3 - to C 12 -cycloalkyl, C 2 - to C 20 -alkenyl, C 1 - to C 20 -alkoxy, aryl, alkylaryl or arylalkyl, in each case substituted by a radical of formula (III) or formula (IV).

[0039] Preference is given to using acylcyanamides or salts thereof according to formula (I) or according to formula (II) whose radical R 1< is a radical from the group consisting of hydrogen, C 1 - to C 20 -alkyl, C 3 - to C 12 -cycloalkyl, C 2 - to C 20 -alkenyl, C 1 - to C 20 -alkoxy or a radical Q, where Q is a radical from the group consisting of C 1 - to C 20 -alkyl, C 3 - to C 12 -cycloalkyl, C 2 - to C 20 -alkenyl, C 1 - to C 20 -alkoxy, each substituted by a radical of formula (III) or formula (IV).

[0040] More preferably, those acylcyanamides or their salts according to formula (I) or according to formula (II) can be used whose radical R 1< represents a radical from the group consisting of hydrogen, C 1 - to C 20 -alkyl, C 2 - to C 20 -alkenyl, C 1 - to C 20 -alkoxy or a radical Q, where Q represents a radical from the group consisting of C 1 - to C 20 -alkyl, C 2 - to C 20 -alkenyl, C 1 - to C 20 -alkoxy, each substituted by a radical of formula (III) or formula (IV).

[0041] Even more preferably, those acylcyanamides or their salts according to formula (I) or according to formula (II) can be used whose radical R 1< represents a radical from the group consisting of hydrogen, C 1 - to C 20 -alkyl, C 2 - to C 20 -alkenyl or a radical Q, where Q represents a radical from the group consisting of C 1 - to C 20 -alkyl, C 2 - to C 20 -alkenyl, each substituted by a radical of formula (III) or formula (IV).

[0042] Particularly preferably, those acylcyanamides or their salts according to formula (I) or according to formula (II) can be used whose radical R 1< represents a radical from the group consisting of hydrogen, C 1 - to C 20 -alkyl or a radical Q, where Q represents a radical from the group consisting of C 1 - to C 20 -alkyl substituted by a radical of formula (III) or formula (IV).

[0043] The free acids of the acylcyanamides according to the invention provide solutions with a pH similar to that of an acetic acid solution. Such acidic solutions are only suitable for specific agricultural applications. Therefore, according to the present invention, salts of the acylcyanamides according to formula (II) are preferred.

[0044] Regarding the variance of the cations, it has been shown that alkali metal salts and alkaline earth metal salts form stable salts of the acylcyanamides according to the invention. Therefore, those acylcyanamides or their salts according to formula (I) or formula (II) are preferred, for which M 1< and M 2< independently of one another are Li, Na, K, ½Ca, or ½Mg. Further preference is given to alkali metal salts. Thus, M 1< and M 2< independently of one another are preferably Li, Na, or K, most preferably Na or K.

[0045] Preferably, according to the present invention, at least one compound from the group of acylcyanamides or a salt thereof according to formula (I) or formula (II) can be used to regulate the generative growth of plants, in particular the generative growth of useful and cultivated plants, preferably the generative growth of fruit trees, or to break the dormancy of fruit trees, where the radicals R 1< , R 2< , R 3< , R 4< , R 5< and the cations M 1< , M 2< independently of one another: R 1< = hydrogen, C 1 - to C 20 -alkyl, C 3 - to C 12 -cycloalkyl, C 2 - to C 20 -alkenyl, C 1 - to C 20 -alkoxy or a radical Q, where Q = C 1 - to C 20 -alkyl, C 3 - to C 12 -cycloalkyl, C 2 - to C 20 -alkenyl, C 1 - to C 20 -alkoxy, in each case substituted by a radical of the formula (III) or formula (IV), M 1< , M 2< = independently of one another Li, Na, K, ½Ca, ½Mg or NR 2< R 3< R 4< R 5< , R 2< , R 3< , R 4< , R 5< = independently of one another hydrogen or C 1 - to C 20 -alkyl.

[0046] Further preferred compounds are those from the group of acylcyanamides or a salt thereof according to formula (I) or according to formula (II), where the radicals R 1< , R 2< , R 3< , R 4< , R 5< and the cations M 1< , M 2< are independently of one another: R 1< = hydrogen, C 1 - to C 20 -alkyl, C 2 - to C 20 -alkenyl, or C 1 - to C 20 -alkoxy, M 1< , M 2< = independently of one another Li, Na, K, ½Ca, ½Mg or NR 2< R 3< R 4< R 5< , R 2< , R 3< , R 4< , R 5< = independently of one another hydrogen or C 1 - to C 20 -alkyl.

[0047] Further preferred compounds are those from the group of acylcyanamides or a salt thereof according to formula (I) or according to formula (II), where the radical R 1< and the cations M 1< , M 2< are independently of one another: R 1< =hydrogen, C 1 - to C 20 -alkyl or C 1 - to C 20 -alkoxy, M 1< , M 2< =independently of one another Li, Na, K, ½Ca or ½Mg.

[0048] Furthermore, according to the present invention, at least one compound from the group of acylcyanamides or a salt thereof of the formula (I) or the formula (II) can be used, wherein the radical R 1< and the cations M 1< , M 2< independently of one another are: R 1< = hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, n-pentyl, n-hexyl, n-heptyl, n-octyl or a radical Q, where Q = methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, each substituted by a radical of the formula (III) or formula (IV) M 1< , M 2< = independently of one another Na or K.

[0049] According to the present invention, at least one compound from the group consisting of sodium formylcyanamide, sodium acetylcyanamide, sodium propionylcyanamide, sodium n-butyrylcyanamide, sodium isobutyrylcyanamide, sodium methoxycarbonylcyanamide, sodium ethoxycarbonylcyanamide, potassium formylcyanamide, potassium acetylcyanamide, potassium propionylcyanamide, potassium n-butyrylcyanamide, potassium isobutyrylcyanamide, potassium methoxycarbonylcyanamide, and potassium ethoxycarbonylcyanamide can be used.

[0050] Alternatively, according to the present invention, at least one compound from the group of acylcyanamides or a salt thereof according to formula (I) or formula (II) can be used, wherein the radicals R 1< , R 2< , R 3< , R 4< , R 5< and the cations M 1< , M 2< independently of one another are: R 1< =hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, or a radical of formula (V) or formula (VI), where X in formula (V) and formula (VI) is: X =alkanediyl, in particular C 1 -C 20 -alkanediyl, M 1< , M 2< =independently of one another Li, Na, K, ½Ca, ½Mg or NR 2< R 3< R 4< R 5< , R 2< , R 3< , R 4< , R 5< =independently of one another hydrogen or C 1 - to C 20 -alkyl.

[0051] Alternatively, according to the present invention, at least one compound from the group of acylcyanamides or a salt thereof according to formula (I) or formula (II) can also be used, wherein the radical R 1< , R 2< , R 3< , R 4< , R 5< and the cations M 1< , M 2< independently of one another are: R 1< = aryl, alkylaryl or arylalkyl, or a radical Q, where Q = aryl, alkylaryl or arylalkyl, each substituted with a radical of the formula (III) or formula (IV), M 1< , M 2< = independently of one another Li, Na, K, ½Ca, ½Mg or NR 2< R 3< R 4< R 5< , R 2< , R 3< , R 4< , R 5< = independently of one another hydrogen or C 1 - to C 20 -alkyl.

[0052] According to the invention, the acylcyanamides according to formulas (I) or (II) can be used to regulate the generative growth of plants, in particular the generative growth of useful and cultivated plants, preferably the generative growth of fruit trees, or to break the dormancy of fruit trees.

[0053] In this context, generative growth of a plant is understood to be the growth of the plant characterized by the development of sexual characteristics such as flowers, seeds, fruits, or plant parts that primarily serve for reproduction. The regulation of generative growth in different plant species can be achieved by various factors such as daylight duration, cold hours, or drought stress. A direct transition from dormancy to generative growth can also be induced.

[0054] Furthermore, dormancy should be understood as a period of rest in the development and life cycle of plants, which is characterized by the plant not growing.

[0055] Furthermore, a useful and cultivated plant is understood to be a plant that is purposefully cultivated, cultivated, or bred through human intervention and is used in whole or in part as food, luxury food, medicine, animal feed, or for technical purposes, for example, as a renewable raw material. Furthermore, fruit trees or fruit tree plants are understood to be perennial flowering and woody plants. The term encompasses perennial trees or shrubs that are persistent (perennial) plants whose axes become woody and remain permanently intact, so that their above-ground shoot system increases in size over the years.

[0056] Such trees or shrubs that bear fruit are also defined as fruit trees and include grapes (Vine), kiwi (Actinidia deliciosa, Actinidia chinensis or Actinidia arguta) , blueberry (Vaccinium myrtillus, Vaccinium corymbosus , Vaccinium virgatum, Vaccinium angustifolium or Vaccinium myrtilloides), cherry (Bird plum or Cherry tree, Plum or damson (Prunus domestica), Apple (Malus domestica or Oriental apple), Pear (Pyrus common, Pyrus pyraster or Pyrus pyrifolia), quince (Quince), peach (Prunus persica), apricot (Prunus armeniaca), raspberry (Rubus idaeus), Persimmon ( Diospyros kaki), Cowardly (Prickly pear) or their cross-breeding products or their cultivated varieties.

[0057] The development of flowers on fruit trees can occur differently on the tree or shrub depending on the genus and species. Cauliflory is the term used in tropical plant families, such as the breadfruit tree ( Artocarpus altis ), jackfruit ( Artocarpus heterophyllus ), Papaya ( Papaya ) or cocoa ( Theobroma cacao), which refers to stem flowering or subsequently stem fruiting, where individual flowers or inflorescences are formed on the woody stem.

[0058] Depending on the genus and species, the development of flowers in fruit trees can also occur via a subform of branch fruiting (ramiflory). In this case, flowers form on the branches. Both forms of flowering are found in cocoa. This occurs on the two- to three-year-old woody branch wood, where collateral buds with meristematic tissue are arranged in the leaf axils, leading to clustered flower formation. According to the present invention, crops and cultivated plants, in particular, can be treated. These crops and cultivated plants can be treated as naturally occurring plants, as hybrids of these plants, or as cultivated varieties.

[0059] Thus, according to a further embodiment, the use of at least one compound from the group of acylcyanamides or a salt thereof according to formula (I) or formula (II) for regulating the generative growth of plants, in particular the generative growth of crop plants and cultivated plants, preferably the generative growth of fruit trees, or for breaking the dormancy of fruit trees is also the subject of the invention, in which the plants, the crop plants and cultivated plants or the fruit trees are selected from the group of plants comprising grapes ( Wine grapevine ), Kiwi ( Actinidia deliciosa, Actinidia chinensis or Actinidia arguta ), blueberry ( Vaccinium myrtillus, Vaccinium corymbosus , Vaccinium virgatum, Vaccinium angustifolium or Vaccinium bilberry ), Cherry ( Bird's-eye plum or Cherry tree ), plum or damson ( Prunus domestica ), Apple ( Domestic apple or Oriental apple ), Pear ( Pyrus commonus, Pyrus pyraster or Pyrus pyrifolia ), quince ( Quince ), peach ( Peach tree ), apricot ( Prunus armeniaca ), raspberry ( Rubus idaeus ), persimmon ( Diospyros kaki ), Cowardly ( Fig tree) or their crossing products or their cultivated varieties.

[0060] According to a further embodiment, the present invention also provides a plant growth regulator concentrate. This concentrate serves for the user-friendly provision of the acylcyanamides according to the invention or their salts as plant growth regulators or dormancy breakers. Thus, the present invention also provides a plant growth regulator concentrate for regulating the generative growth of plants, in particular the generative growth of crops and cultivated plants, preferably the generative growth of fruit trees, or for breaking the dormancy of fruit trees, comprising: a) at least one active ingredient from the group of acylcyanamides or a salt thereof according to formula (I) or formula (II), where the following applies to formula (I) and formula (II): where the radicals R 1< , R 2< , R 3< , R 4< , R 5< and the cations M 1< , M 2< independently of one another: R 1< = hydrogen, C 1 - to C 20 -alkyl, C 3 - to C 12 -cycloalkyl, C 2 - to C 20 -alkenyl, C 1 - to C 20 -alkoxy, aryl, alkylaryl, arylalkyl or a radical Q, where the following applies to Q: Q = C 1 - to C 20 -alkyl, C 3 - to C 12 -cycloalkyl, C 2 - to C 20 -alkenyl, C 1 - to C 20 -alkoxy, aryl, alkylaryl or arylalkyl, in each case substituted by a radical of the formula (III) or formula (IV) M 1< , M 2< = independently of one another Li, Na, K, ½Ca, ½Mg or NR 2< R 3< R 4< R 5< , R 2< , R 3< , R 4< , R 5< = independently of one another hydrogen or C 1 - to C 20 -alkyl, b) at least one additive from the group of solvents, oils, surface-active substances or emulsifiers which is harmless or permitted for agricultural purposes, wherein the concentrate has a concentration of active ingredient in the range of 200 to 600 g / l.

[0061] Another object of the present invention is a plant growth regulator concentrate for regulating the generative growth of plants or for breaking the dormancy of fruit trees, comprising a) at least one active ingredient from the group of acylcyanamides or a salt thereof according to formula (I) or formula (II), where the following applies to formula (I) and formula (II): where for the radicals R 1< , R 2< , R 3< , R 4< , R 5< and the cations M 1< , M 2< independently of one another: R 1< = hydrogen, an alkyl radical selected from the group methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, 2-ethylpropyl or n-hexyl, an alkenyl radical selected from the group ethenyl, propenyl, butenyl, pentenyl, hexenyl, butadienyl, pentadienyl, hexadienyl or hexatrienyl, C 3 - to C 12 -cycloalkyl, C 1 - to C 20 -alkoxy, aryl, alkylaryl or arylalkyl, or a radical Q, where Q = C 1 - to C 20 -alkyl, C 3 - to C 12 -cycloalkyl, C 2 - to C 20 -alkenyl, C 1 - to C 20 -alkoxy, aryl, alkylaryl or arylalkyl, each substituted by a radical of the formula (III) or formula (IV) M 1< , M 2< = independently of one another Li, Na, K, ½Ca, ½Mg or NR 2< R 3< R 4< R 5< , R 2< , R 3< , R 4< , R 5< = independently of one another hydrogen or C 1 - to C 20 -alkyl, b) at least one additive from the group of solvents, oils, surface-active substances or emulsifiers which is harmless or permitted for agricultural purposes, wherein the concentrate has a concentration of active ingredient in the range of 100 to 600 g / l.

[0062] All acylcyanamides described herein, as well as all acylcyanamides described herein as preferred or alternatively preferred, can be used as the active ingredient in this concentrate, wherein the concentrate has an active ingredient concentration in the range of 100 to 600 g / l. According to a preferred embodiment, the concentrate has an active ingredient concentration in the range of 200 to 600 g / l, in particular an active ingredient concentration in the range of 300 to 600 g / l.

[0063] According to a preferred embodiment, the concentrate is in the form of a solution, emulsifiable solution or emulsion, in particular as an aqueous solution or as an emulsion.

[0064] The term emulsion is understood here and in the sense of the present invention to mean a mixture of at least two liquid components that are not completely miscible with one another and that in particular have a miscibility gap. Here, one component is distributed as a dispersed or inner liquid phase in another coherent outer liquid phase. The term oil-in-water emulsion, also referred to as O / W emulsion, is understood in the sense of the present invention to mean an emulsion in which an oil phase is dispersed in a coherent hydrophilic, preferably aqueous phase. The oil phase comprises a hydrophobic, water-immiscible organic phase comprising an oil. Here, the oil phase is dispersed in the hydrophilic, preferably aqueous phase in the form of droplets.The term "water-in-oil emulsion," also known as a W / O emulsion, is understood for the purposes of the present invention to mean an emulsion in which a water phase or an aqueous phase is dispersed in a coherent hydrophobic phase, preferably an oil phase. The term "emulsion" also includes miniemulsions and microemulsions for the purposes of the present invention.

[0065] Furthermore, an emulsifiable solution is to be understood as a solution which, after addition to water (or addition of water to the composition), forms an emulsion on its own or which, after addition to water (or addition of water to the composition) and mechanical mixing, such as stirring, forms an emulsion.

[0066] Thus, a plant growth regulator concentrate for regulating the generative growth of plants, in particular the generative growth of crops and cultivated plants, preferably the generative growth of fruit trees, or for breaking the dormancy of fruit trees, is also the subject of the present invention, which comprises a solution, emulsifiable solution or emulsion, in particular an aqueous solution or emulsion, which in turn comprises: a) at least one active ingredient from the group of acylcyanamides or a salt thereof according to formula (I) or formula (II), where the following applies to formula (I) and formula (II): where the radicals R 1< , R 2< , R 3< , R 4< , R 5< and the cations M 1< , M 2< independently of one another: R 1< = hydrogen, C 1 - to C 20 -alkyl, C 3 - to C 12 -cycloalkyl, C 2 - to C 20 -alkenyl, C 1 - to C 20 -alkoxy, aryl, alkylaryl, arylalkyl or a radical Q, where the following applies to Q: Q = C 1 - to C 20 -alkyl, C 3 - to C 12 -cycloalkyl, C 2 - to C 20 -alkenyl, C 1 - to C 20 -alkoxy, aryl, alkylaryl or arylalkyl, in each case substituted by a radical of the formula (III) or formula (IV) M 1< , M 2< = independently of one another Li, Na, K, ½Ca, ½Mg or NR 2< R 3< R 4< R 5< , R 2< , R 3< , R 4< , R 5< = independently of one another hydrogen or C 1 - to C 20 -alkyl, b) at least one additive from the group of solvents, oils, surface-active substances or emulsifiers which is harmless or permitted for agricultural purposes, wherein the solution, the emulsifiable solution or the emulsion has a concentration of active ingredient according to a) in the range from 200 to 600 g / l.

[0067] A further subject of the present invention is a plant growth regulator concentrate for regulating the generative growth of plants, in particular the generative growth of crops and cultivated plants, preferably the generative growth of fruit trees, or for breaking the dormancy of fruit trees, which comprises a solution, emulsifiable solution or emulsion, in particular an aqueous solution or emulsion, which in turn comprises: a) at least one active ingredient from the group of acylcyanamides or a salt thereof according to formula (I) or formula (II), where the following applies to formula (I) and formula (II): where for the radicals R 1< , R 2< , R 3< , R 4< , R 5< and the cations M 1< , M 2< independently of one another: R 1< = hydrogen, an alkyl radical selected from the group methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, 2-ethylpropyl or n-hexyl, an alkenyl radical selected from the group ethenyl, propenyl, butenyl, pentenyl, hexenyl, butadienyl, pentadienyl, hexadienyl or hexatrienyl, C 3 - to C 12 -cycloalkyl, C 1 - to C 20 -alkoxy, aryl, alkylaryl or arylalkyl, or a radical Q, where Q = C 1 - to C 20 -alkyl, C 3 - to C 12 -cycloalkyl, C 2 - to C 20 -alkenyl, C 1 - to C 20 -alkoxy, aryl, alkylaryl or arylalkyl, each substituted by a radical of the formula (III) or formula (IV) M 1< , M 2< = independently of one another Li, Na, K, ½Ca, ½Mg or NR 2< R 3< R 4< R 5< , R 2< , R 3< , R 4< , R 5< = independently of one another hydrogen or C 1 - to C 20 -alkyl, b) at least one additive from the group of solvents, oils, surface-active substances or emulsifiers which is harmless or permitted for agricultural purposes, wherein the concentrate has a concentration of active ingredient according to a) in the range from 100 to 600 g / l.

[0068] Preferably, the plant growth regulator concentrate, which more preferably is a solution, an emulsifiable solution or an emulsion, comprises or comprises: a) at least one active ingredient from the group of acylcyanamides or a salt thereof according to formula (I) or formula (II), and b) at least one additive from the group of solvents which is safe or permitted for agricultural purposes, and optionally c) at least one additive from the group of oils, surface-active substances or emulsifiers which is safe or permitted for agricultural purposes, and optionally d) at least one further formulation aid, wherein the concentrate has a concentration of active ingredient in the range of 100 to 600 g / l.

[0069] Further preferred is a plant growth regulator concentrate which is in particular present as a solution, emulsifiable solution or emulsion, in particular as an aqueous solution or as an emulsion, which in turn comprises: a) at least one active ingredient from the group of acylcyanamides or a salt thereof according to formula (I) or formula (II), where the radicals R 1< , R 2< , R 3< , R 4< , R 5< and the cations M 1< , M 2< independently of one another: R 1< = hydrogen, C 1 - to C 20 -alkyl, C 3 - to C 12 -cycloalkyl, C 2 - to C 20 -alkenyl, C 1 - to C 20 -alkoxy or a radical Q, where the following applies to Q: Q = C 1 - to C 20 -alkyl, C 3 - to C 12 -cycloalkyl, C 2 - to C 20 -alkenyl, C 1 - to C 20 -alkoxy, in each case substituted by a radical of formula (III) or formula (IV), M 1< , M 2< = independently of one another Li, Na, K, ½Ca, ½Mg or NR 2< R 3< R 4< R 5< , R 2< , R 3< , R 4< , R 5< =independently of one another hydrogen or C 1 - to C 20 -alkyl.

[0070] Particularly preferred is a plant growth regulator concentrate which is in particular present as a solution, emulsifiable solution or emulsion, in particular as an aqueous solution or as an emulsion, which in turn comprises: a) at least one active ingredient from the group consisting of sodium formylcyanamide, sodium acetylcyanamide, sodium propionylcyanamide, sodium n-butyrylcyanamide, sodium isobutyrylcyanamide, sodium methoxycarbonylcyanamide, sodium ethoxycarbonylcyanamide, potassium formylcyanamide, potassium acetylcyanamide, potassium propionylcyanamide, potassium n-butyrylcyanamide, potassium isobutyrylcyanamide, potassium methoxycarbonylcyanamide or potassium ethoxycarbonylcyanamide, b) at least one additive from the group consisting of solvents which is safe or permitted for agricultural purposes, and c) at least one additive from the group consisting of oils, surface-active substances or emulsifiers which is safe or permitted for agricultural purposes, wherein the concentrate has a concentration of active ingredient in the range of 100 to 600 g / l.

[0071] According to the present invention, the plant growth concentrate may contain a solvent. In the context of the present invention, a solvent is understood to mean any solvent suitable for use in agriculture. Suitable solvents are therefore those that are compatible with plants. Particular preference is given to water or organic solvents, especially water-miscible organic solvents.

[0072] In the context of the present invention, a water-miscible organic solvent is understood to mean any organic solvent which is, by definition, different from water and which, in a mass ratio of 1:1 with water at 20 °C, results in a single-phase system.

[0073] The investigations underlying this invention have shown that, in particular, organic solvents selected from the group of water-soluble alcohols, ketones, nitriles, amides, glycols, polyglycols and mixtures thereof can be used as water-miscible organic solvents.

[0074] Preferred solvents are thus water and organic solvents selected from the group ethanol, isopropanol, n-propanol, glycol, glycerin, polyglycol, acetone, methyl ethyl ketone, acetonitrile, propionitrile, formamide, dimethylformamide, N-methylpyrrilidone, and mixtures thereof.

[0075] According to a particularly preferred embodiment of the invention, the concentrate comprises water, ethanol, isopropanol, n-propanol, glycol, glycerin, polyglycol, or mixtures thereof as solvent. Concentrates containing these solvents are particularly stable liquid formulations that can be stored for extended periods.

[0076] Thus, the present invention also relates to plant growth regulator concentrate which is a solution, an emulsifiable solution or an emulsion which comprises, as solvent, a solvent selected from the group consisting of water, ethanol, isopropanol, glycol, polyglycol, glycerol or mixtures of these solvents.

[0077] According to an alternative formulation, the concentrate can also be formulated as an emulsifiable solution. Therefore, according to a further development of the invention, the present invention also particularly relates to a concentrate formulated as an emulsifiable solution and containing less than 10 wt.%, in particular less than 5 wt.%, particularly preferably less than 3 wt.% water, further preferably less than 2 wt.% water, and most preferably less than 1 wt.% water.

[0078] According to the present invention, the plant growth concentrate may contain an oil. In the context of the present invention, an oil is understood to mean any oil suitable for use in agriculture. Suitable oils are therefore those oils that are compatible with plants. In particular, the oil can be selected from the group of natural oils, in particular oils of animal or plant origin, and synthetic oils. According to the present invention, natural oils, in particular vegetable oils, can be used as the oil. Vegetable oils are generally known and commercially available.The term vegetable oils in the sense of the present invention refers to oils from oil-yielding plant species such as soybean oil, corn germ oil, sunflower oil, rapeseed oil, cottonseed oil, linseed oil, coconut oil, palm oil, safflower oil, peanut oil, walnut oil, olive oil or castor oil, in particular rapeseed oil, whereby the vegetable oils also include their transesterification products, e.g. alkyl esters such as rapeseed oil methyl ester or rapeseed oil ethyl ester.

[0079] The vegetable oils according to the present invention are preferably mixtures of C 10 to C 24 fatty acid esters. These C 10 to C 24 fatty acid esters are, for example, esters of unsaturated or saturated C 10 to C 24 fatty acids, in particular with an even number of carbon atoms, further preferably selected from the group consisting of capric acid (decanoic acid), lauric acid (dodecanoic acid), myristic acid (tetradecanoic acid), palmitic acid (hexadecanoic acid), stearic acid (octadecanoic acid), arachidic acid (eicosanoic acid), palmitoleic acid (hexadecyl-9-enoic acid), petroselinic acid (octadecyl-6-enoic acid), oleic acid (octadecyl-9-enoic acid), elaidic acid (octadecyl-9-enoic acid), gadoleic acid (eicosanoic-9-enoic acid), erucic acid (13-docosenoic acid), linoleic acid (octadec-9,12-dienoic acid), alpha-linolenic acid (octadec-9,12,15-trienoic acid), gamma-linolenic acid (octadec-6,9,12-trienoic acid) or mixtures thereof.

[0080] Examples of vegetable oils are C 10 to C 24 fatty acid esters of glycerol or glycol with C 10 to C 24 fatty acids, in particular esters of the acids listed, or C 10 to C 24 fatty acid esters, in particular esters of the acids listed, as can be obtained, for example, by transesterification of the aforementioned glycerol or glycol esters of the C 10 to C 24 fatty acid with C 1 to C 20 alcohols, such as methanol, ethanol, propanol or butanol.

[0081] The vegetable oils can be present in the liquid compositions according to the invention, for example, in the form of commercially available vegetable oils, in particular rapeseed oils such as rapeseed oil methyl esters, for example Phytorob ®< B (Novance, France), Edenor ®< MESU and Agnique ®< ME series (Cognis, Germany), Radia ®< (ICI) or Prilube ®< (Petrofina).

[0082] Insofar as synthetic oils are used, mineral oil, paraffin oil, white oil and synthetic fatty acid esters, in particular esters of fatty acids with an odd number of carbon atoms, such as C 11 to C 19 fatty acids, in particular selected from the group of undecanoic acid, tridecanoic acid, pentadecanoic acid, margaric acid (heptadecanoic acid) and nonadecanoic acid, with mono-, di- or trihydric C 1 to C 5 alcohols, in particular methanol, ethanol, propanol or butanol, are preferred.

[0083] According to the present invention, the oil used can therefore be, in particular, an oil selected from the group consisting of mineral oil, paraffin oil, white oil, saturated linear or branched aliphatic hydrocarbons, esters of saturated or unsaturated fatty acids with mono-, di- or trihydric C 1 to C 5 alcohols, ethers of fatty alcohols with C 1 to C 5 alcohols and mixtures thereof.

[0084] According to the present invention, oils from the group of mineral oils, mineral oils with a reduced aromatic content, mineral oils without an aromatic content, fatty oils, ie glycerol esters of fatty acids with 4 to 24 C atoms, esters of C 1 to C 20 alcohols with fatty acids with 4 to 24 C atoms, preferably methyl or ethyl esters of fatty acids with 4 to 24 C atoms can also be used.

[0085] Particularly suitable are oils from the group comprising esters of C 1 to C 20 alcohols with fatty acids having 4 to 24 C atoms, in particular methyl or ethyl esters of fatty acids having 4 to 24 C atoms.

[0086] Thus, the present invention also relates to a plant growth regulator concentrate which is a solution, an emulsifiable solution or an emulsion which comprises as oil an oil from the group of vegetable oils, in particular vegetable oils from the group of C 10 to C 24 fatty acid esters, in particular methyl, ethyl, glyceryl or glycol esters of C 10 to C 24 fatty acids, in particular rapeseed oil methyl ester.

[0087] According to the present invention, the plant growth regulator concentrate may in particular comprise 0.1 to 20 wt.% of at least one oil, in particular a vegetable oil. However, the plant growth regulator concentrate may preferably also comprise 0.1 to 15 wt.% of at least one oil, in particular a vegetable oil, and more preferably 0.1 to 12 wt.% of at least one oil, in particular a vegetable oil, and particularly preferably 0.1 to 10 wt.% of at least one oil.

[0088] Surface-active substances (hereinafter also referred to as surfactants) that can be used are, in particular, those with an HLB value of 5 to 20. Furthermore, cationic, anionic, or non-ionic surfactants can also be used as surface-active substances. Non-ionic surfactants are particularly preferred.

[0089] Thus, the present invention also relates to a plant growth regulator concentrate which is a solution, an emulsifiable solution or an emulsion which comprises, as surface-active substance, a surface-active substance from the group of non-ionic surfactants.

[0090] More preferably, nonionic surfactants can be used which contain one or more compounds from the group of ethoxylates according to formula (VII), fatty alcohol glucosides according to formula (VIII) or mixtures thereof, where for formula (VII) and (VIII), R 11< -O-(CH 2 CH 2 O) n -H Formula (VII) where for the radicals R 11< , R 12< and the indices n, m simultaneously or independently: R 11< = a linear or branched alkyl or alkenyl group having 6 to 24 carbon atoms, a partially or fully fluorinated alkyl group having 6 to 18 carbon atoms, a phenyl group, an alkyl-substituted phenyl group, a mono- or polyfunctional siloxane group, R 12< = a linear or branched alkyl or alkenyl group having 6 to 24 carbon atoms, n = a number from 2 to 20, m = a number from 1 to 5.

[0091] In the context of the present invention, a mono- or polyfunctional siloxane group is to be understood as meaning in particular a siloxane group which is obtained by mixed hydrolysis from a) one or more chlorosilanes from the group consisting of trimethylchlorosilane, dimethyldichlorosilane and methyltrichlorosilane, and b) one or more 3-heteropropyl-substituted chlorosilanes from the group consisting of 3-heteropropyl-trichlorosilane, 3-heteropropylmethyldichlorosilane and 3-heteropropyl-dimethylchlorosilane, where 3-heteropropyl has the meaning: 3-chloropropyl, 3-hydroxypropyl or 3-(hydroxyethoxy)propyl, can be produced.

[0092] Typical mono- or polyfunctional siloxane groups that can be prepared from these building blocks are listed below in the formulas, where formula (IX) stands for a monofunctional siloxane group, formula (X) for a bifunctional siloxane group and formulas (XI) and (XII) for a v-functional siloxane group, and the following applies to formulas (IX), (X), (XI) and (XII): (H 3 C) 3 Si-O-((CH 3 ) 2 SiO) x -Si(CH 3 ) 2 -(CH 2 ) 3 - Formula (IX) where the index x is: x = a number from 0 to 15, in particular a number from 0 to 10, in particular a number from 3 to 10, HIGH 2 CH 2 ) y -O-(CH 2 ) 3 -((CH 3 ) 2 SiO) z -Itself 3 ) 2 -(CH 2 ) 3 - Formula (X) where the indices y and z are: y = a number from 2 to 20, in particular a number from 2 to 10, in particular a number from 3 to 10, z = a number from 0 to 10, in particular a number from 0 to 5, in particular a number from 1 to 3, where the indices y, u and v are: y = a number from 2 to 20, in particular a number from 2 to 10, in particular a number from 3 to 10, u = a number from 0 to 15, in particular a number from 0 to 10, in particular a number from 0 to 3, v = a number from 0 to 4, in particular a number from 0 to 3.

[0093] Particularly preferred are v-functional siloxane groups, in particular siloxane groups of the formula (XII), which represents a special case of the formula (XI) for u = v = 0, where for formula (XII) the following applies:

[0094] According to a particularly preferred embodiment, an ethoxylate according to formula (VII) is used as the non-ionic surfactant, where the radical R 11< and the index n are: R 11< = linear or branched alkyl group having 8 to 18 carbon atoms, or alkyl-substituted phenyl group, or a monofunctional siloxane of the formula (VII) with x = a number from 3 to 10, or a bifunctional siloxane of the formula (VIII) with z = a number from 1 to 3 and y = a number from 2 to 10, or a polyfunctional siloxane group of the formula (X) with u = a number from 0 to 3 and v = a number from 0 to 3 and y = a number from 2 to 10, in particular a number from 3 to 10, n = a number from 2 to 20, in particular a number from 2 to 10, in particular a number from 3 to 10.

[0095] According to a further preferred embodiment, a mixture of different ethoxylates according to formula (VII) can also be used as the nonionic surfactant. A mixture of at least two different ethoxylates according to formula (VII) has proven particularly effective, where the radical R 11< and the index n are: R 11< = a polyfunctional siloxane group of the formula (XI) with u = a number from 0 to 3 and v = a number from 0 to 3 and y = a number from 2 to 10, n = a number from 2 to 20, in particular a number from 2 to 10, in particular a number from 3 to 10.

[0096] According to a further preferred embodiment, a mixture of different ethoxylates according to formula (VII) can also be used as the nonionic surfactant. A mixture of at least two different ethoxylates according to formula (VII) has proven particularly effective, where the radical R 11< and the index n are: R 11< =n-dodecyl, n-hexadecyl and n-octadecyl, n =a number from 2 to 20, in particular a number from 2 to 10.

[0097] Very particular preference is given to ethoxylates according to formula (VII), where the radical R 1< and the index n are: R 11< = n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, methyldecyl, methyldodecyl, methyltetradecyl, or a siloxane of the formula (XII), n = a number from 4 to 8.

[0098] According to an alternative preferred embodiment, it is provided that a fatty alcohol glucoside according to formula (VIII) is used as the non-ionic surfactant, where the radical R 12< and the index m are: R 12< =linear alkyl group having 8 to 18 carbon atoms, m =a number from 2 to 5.

[0099] Fatty alcohol glucosides according to formula (VIII) are particularly preferred, where the radical R 12< and the index m are: R 12< =n-hexadecyl or n-octadecyl, m =a number from 3 to 5

[0100] According to the present invention, the plant growth regulator concentrate may in particular comprise 0.1 to 10 wt.% of at least one surfactant, in particular a nonionic surfactant. However, the composition may particularly preferably also comprise 0.1 to 5 wt.% of at least one surfactant, in particular a nonionic surfactant, and most preferably 0.1 to 3 wt.% of at least one surfactant, in particular a nonionic surfactant.

[0101] The plant growth regulator concentrate according to the invention can comprise at least one emulsifier as a harmless or approved additive. The concentrate according to the invention preferably comprises at least one emulsifier selected from the group of oil-in-water emulsifiers (O / W emulsifiers), water-in-oil emulsifiers (W / O emulsifiers), oil-in-water-in-oil emulsifiers (O / W / O emulsifiers), or water-in-oil-in-water emulsifiers (W / O / W emulsifiers), in particular at least one oil-in-water emulsifier.

[0102] According to a particularly preferred embodiment, the composition comprises at least one oil-in-water emulsifier and / or a non-ionic emulsifier and very particularly preferably at least one non-ionic emulsifier from the class of oil-in-water emulsifiers.

[0103] Thus, the present invention also relates to a plant growth regulator concentrate which is a solution, an emulsifiable solution or an emulsion which comprises, as emulsifier, an emulsifier from the group of non-ionic oil-in-water emulsifiers.

[0104] Preferred nonionic emulsifiers are selected from the group containing fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, ethoxylated fatty alcohols, ethoxylated nonylphenols, fatty acid monoglycerides, fatty acid diglycerides, ethoxylated and hydrogenated or non-hydrogenated castor oil and fatty acid alkanolamides.

[0105] Preferred cationic emulsifiers are selected from the group containing long-chain quaternary ammonium compounds such as alkyltrimethylammonium salts and dialkyldimethylammonium salts with C8 to C22 alkyl groups.

[0106] Preferred anionic emulsifiers are selected from the group containing fatty alcohol sulfates, alkyl ether sulfates and alkylbenzenesulfonates.

[0107] Preferred amphoteric emulsifiers are selected from the group containing betaines such as fatty acid amidoalkyl betaines and sulfobetaines and C8 to C22 alkyl betaines.

[0108] Particularly preferred are nonionic emulsifiers from the class of ethoxylated fatty alcohols, especially ethoxylated C8 to C20 alkyl alcohols. Also preferred is a nonionic O / W emulsifier from the class of ethoxylated C8 to C20 alkyl alcohols, and most preferably an iso-C13 ethoxylate.

[0109] According to the present invention, the plant growth regulator concentrate may in particular comprise 0.1 to 10 wt.% of at least one emulsifier. However, the composition may particularly preferably also comprise 0.1 to 5 wt.% of at least one emulsifier, and most preferably 0.1 to 3 wt.% of at least one emulsifier.

[0110] Within the scope of the present invention, it may further be provided that the plant growth regulator concentrate comprises or contains further ingredients, namely formulation aids.

[0111] It is preferably provided that the concentrate further comprises or contains at least one formulation aid, in particular one approved for agricultural purposes, from the group of pH regulators, dyes, thickeners, dispersants, solubilizers, viscosity modifiers, markers and bittering substances.

[0112] These formulation auxiliaries can be included or contained in the solution in an amount of up to 5% by weight. These formulation auxiliaries can be used in addition to the additives described herein from the group of solvents, oils, surfactants, and emulsifiers and have no effect on the plant physiological activity of the spray mixture prepared from a concentrate according to the invention. Thus, these additional formulation auxiliaries serve exclusively application-specific requirements.

[0113] It is particularly preferred that the formulation auxiliaries be comprised or contained in an amount of up to 4 wt.%, more preferably up to 3 wt.%, and particularly preferably up to 2 wt.%. Should the concentrate according to the invention comprise formulation auxiliaries due to application-specific requirements, the concentrate may preferably comprise or contain at least 0.01 wt.% of formulation auxiliaries, in particular at least 0.1 wt.% (in each case based on the total weight of the concentrate).

[0114] According to the present invention, the plant growth concentrate has an active ingredient concentration in the range of 100 to 600 g / l. Preferably, the concentrate according to the invention comprises or contains at least 10% by weight and at most 60% by weight of at least one compound from the group of acylcyanamides or a salt thereof according to formula (I) or formula (II) (based on the total weight of the concentrate). More preferably, the concentrate according to the invention comprises or contains at least 20% by weight, more preferably at least 30% by weight, and most preferably at least 35% by weight of at least one compound from the group of acylcyanamides or a salt thereof according to formula (I) or formula (II) (based on the total weight of the concentrate).

[0115] Thus, a plant growth regulator concentrate is also the subject of the present invention, in particular a plant growth regulator concentrate which is in the form of a solution, emulsifiable solution or emulsion, which a) 10 to 60% by weight of at least one active ingredient from the group of acylcyanamides or a salt thereof according to formula (I) or formula (II), and b) 40 to 90% by weight of at least one solvent, in particular water or a water-miscible solvent, and optionally c) 0.1 to 12% by weight of at least one oil, a surfactant and / or an emulsifier, and optionally d) 0.01 to 5% by weight of at least one further formulation aid, wherein the proportions a) to d) add up to 100% by weight, and wherein in particular the at least one compound from the group of acylcyanamides or a salt thereof is present in the concentrate in dissolved form.

[0116] Most preferably, the plant growth regulator concentrate according to the present invention comprises a) 30 to 60% by weight of at least one active ingredient from the group of acylcyanamides or a salt thereof according to formula (I) or formula (II), b) 40 to 70% by weight of at least one solvent, in particular water or a water-miscible solvent, and optionally c) 0.1 to 8% by weight of at least one oil, an emulsifier or a surfactant, and optionally, d) 0.01 to 3% by weight of at least one further formulation aid, wherein the proportions a) to d) add up to 100% by weight, and wherein in particular the at least one compound from the group of acylcyanamides or a salt thereof is present in the concentrate in dissolved form.

[0117] However, it can also be provided that the plant growth regulator concentrate according to the present invention does not contain any further ingredients besides the aforementioned ingredients a), b), c) and optionally d) and thus consists of the aforementioned ingredients.

[0118] In a further advantageous embodiment of the invention, the concentrate according to the invention has a surface tension of less than 70 mN / m, preferably less than 60 mN / m, and very particularly preferably less than 40 mN / m at a temperature of 25 °C, wherein at the same time or independently thereof it can be provided that the concentrate has a surface tension of at least 5 mN / m at a temperature of 25 °C.

[0119] In a further advantageous embodiment of the invention, the concentrate according to the invention has a viscosity of less than 1 Pa*s at a temperature of 25°C. The concentrate according to the invention preferably has a viscosity of less than 500 mPa*s, more preferably less than 100 mPa*s, and even more preferably less than 50 mPa*s at 25°C.

[0120] The plant growth regulator concentrates according to the invention can provide high concentrations of active ingredients. However, these concentrations are far too high for the application of the active ingredients described herein. These concentrates must be diluted before use, especially as a spray, dip, or spread solution.

[0121] In the application tests, it has been shown that the active ingredients described herein from the group of acylcyanamides or a salt thereof according to formula (I) or formula (II), in particular as a spray, dip or spread solution, can be used preferably in a concentration in the range of 0.05 to 1 mol / l.

[0122] It has further been shown that these active ingredients, in particular as a spray, dip or spread solution, can be used in a concentration in the range from 0.05 to 0.8 mol / l, in particular 0.05 to 0.6 mol / l and particularly preferably 0.05 to 0.5 mol / l.

[0123] It has further been shown that these active ingredients, in particular as a spray, dip or spread solution, can be used in a concentration in the range from 0.1 to 1 mol, in particular 0.1 to 0.8 mol / l, in particular 0.1 to 0.6 mol / l and particularly preferably 0.1 to 0.5 mol / l.

[0124] Furthermore, the use of the plant growth regulator concentrate described here or of a spray or dip solution prepared from or with this concentrate for regulating the generative growth of plants, in particular the generative growth of useful and cultivated plants, preferably the generative growth of fruit trees, or for breaking the dormancy of fruit trees is encompassed by the present invention.

[0125] According to a further embodiment, the present invention also relates to a plant growth regulator spray solution for regulating the generative growth of plants, in particular the generative growth of crops and cultivated plants, preferably the generative growth of fruit trees, or for breaking the dormancy of fruit trees, comprising a solution or emulsion, which comprises: a) at least one active ingredient from the group of acylcyanamides or a salt thereof according to formula (I) or formula (II), where the following applies to formula (I) and formula (II): where the radicals R 1< , R 2< , R 3< , R 4< , R 5< and the cations M 1< , M 2< independently of one another: R 1< = hydrogen, C 1 - to C 20 -alkyl, C 3 - to C 12 -cycloalkyl, C 2 - to C 20 -alkenyl, C 1 - to C 20 -alkoxy, aryl, alkylaryl or arylalkyl, or a radical Q, where the following applies to Q: Q = C 1 - to C 20 -alkyl, C 3 - to C 12 -cycloalkyl, C 2 - to C 20 -alkenyl, C 1 - to C 20 -alkoxy, aryl, alkylaryl or arylalkyl, in each case substituted by a radical of the formula (III) or formula (IV) M 1< , M 2< = independently of one another Li, Na, K, ½Ca, ½Mg or NR 2< R 3< R 4< R 5< R 2< , R 3< , R 4< , R 5< = independently of one another hydrogen or C 1 - to C 20 -alkyl, b) at least one additive or approved auxiliary substance from the group of solvents, oils, surface-active substances, emulsifiers which is safe for agricultural purposes, wherein the aqueous solution has a concentration of active ingredient in the range of 0.05 to 1 mol / l, in particular 0.05 to 0.8 mol / l, in particular 0.05 to 0.6 mol / l, in particular 0.05 to 0.5 mol / l.

[0126] Thus, according to a further embodiment, a method for regulating the generative growth of plants, in particular the generative growth of useful and cultivated plants, preferably the generative growth of fruit trees, or for breaking the dormancy of fruit trees, is also the subject of the present invention, comprising applying an aqueous solution comprising at least one active ingredient from the group of the acylcyanamides or a salt thereof according to formula (I) or formula (II) to the branches, shoots or buds of the plants by dipping, brushing or spraying, during the dormancy of the plants, the useful and cultivated plants or the fruit trees.

[0127] The following examples are intended to explain the nature of the invention in more detail. Examples Synthesis examples Example A-1 Synthese von Natriumacetylcyanamid (CAS 84946-07-6) aus festem Cyanamid

[0128] 180.1 g (1.0 mol) of a 30% solution of sodium methylate were initially introduced. A total of 42.25 g (1.005 mol) of solid cyanamide was added in portions at a maximum temperature of 25 °C while cooling thoroughly. Then, 134.83 g (1.82 mol) of methyl acetate were added, and the suspension was heated to reflux (approx. 64 °C) for 10 hours. The reaction mixture was cooled to 10 °C, the precipitated sodium acetylcyanamide fraction 1 was filtered off and dried at 60 °C. The resulting mother liquor was evaporated to half its volume, cooled to 10 °C, and the precipitated fraction 2 was filtered off and dried. The following were obtained: Fraction 1: 75 g (71 % yield) with 99.4 % purity, melting point 239 °C Fraction 2: 19 g (18 % yield) with 99.0 % purity, melting point 238 °C 1< H-NMR in DMSO 1.70 ppm (s), 13< C-NMR 180.75, 122.60, 25.26 ppm Example A-1a Synthesis of sodium acetylcyanamide (CAS 84946-07-6) from sodium hydrogen cyanamide

[0129] 120 g of methanol and 88.8 g (1.20 mol) of methyl acetate were initially introduced. 64.04 g (1.0 mol) of sodium hydrogen cyanamide were suspended therein. The reaction mixture was heated to 70 °C for 10 hours. It was then completely evaporated to dryness, and the resulting solid was dried under vacuum at 60 °C. This yielded 106 g (100% yield) of sodium acetylcyanamide with a purity of 98.9%. Example A-1b Synthesis of acetylcyanamide (CAS 5634-51-5) as free NH acid

[0130] 120 g of methanol and 88.8 g (1.20 mol) of methyl acetate were initially introduced. 64.04 g (1.0 mol) of sodium hydrogen cyanamide were suspended therein. The reaction mixture was heated to 70 °C for 10 hours. It was then cooled, and a further 500 g of methanol was added. At 10 to 20 °C, 49.0 g (0.5 mol) of concentrated sulfuric acid were added, causing sodium sulfate to precipitate. The suspension was filtered, washed with methanol, and the combined filtrates were largely evaporated. This gave 84 g of an oil with a density of 1.100 g / cm 3 and a refractive index n D of 1.425, each measured at 20 °C. The yield was quantitative. Example A-1c Synthesis of potassium acetylcyanamide (CAS 1146597-19-4)

[0131] 280.4 g (1.0 mol) of a 25% solution of potassium methylate were initially introduced. With thorough cooling at a maximum temperature of 25 °C, a total of 42.25 g (1.005 mol) of solid cyanamide was added in portions. Then, 134.83 g (1.82 mol) of methyl acetate were added, and the suspension was heated to reflux (approx. 64 °C) for 10 hours. The reaction mixture was evaporated to approximately half its volume and cooled to 10 °C. The precipitated solid was filtered off and dried at 60 °C. This gave 94 g of a white solid with a nitrogen content of 23.0%. The yield was 77%. Example A-2 Synthesis of sodium formylcyanamide (CAS 71675-63-3)

[0132] 909.5 g (5.0 mol) of a 29.7% sodium methylate solution were initially introduced. A total of 211.05 g (5.0 mol) of 99.6% solid cyanamide was added in portions at 10 to 20 °C while cooling thoroughly. 250 ml of methanol was then added to ensure good stirrability. Subsequently, 309.55 g (5.0 mol) of 97.0% methyl formate were added while cooling. The reaction mixture was heated to approximately 38 °C (strong reflux) for a total of 18 hours. It was then cooled to 10 °C, and the precipitated product (Fraction 1) was filtered off and dried at 60 °C. The filtrate was evaporated to dryness and then dried (Fraction 2). The following were obtained: Fraction 1: 343.9 g (75% yield) with 30.22% N content, melting point 256 °C Fraction 2: 16.9 g (25% yield) with 30.34% N content, melting point 255 °C 1< H-NMR in DMSO: 8.43 ppm, 13< C-NMR 171.88, 122.5 ppm Examples A-3 to A-15 Synthesis of further sodium acylcyanamides

[0133] Further syntheses were carried out analogously to Example A-1a from sodium hydrogen cyanamide. Depending on the desired target compound, 1.2 mol of a carboxylic acid methyl ester was initially introduced into 120% methanol, 64.04 g (1.0 mol) of sodium hydrogen cyanamide were suspended therein, and the reaction mixture was heated to reflux (approx. 65 °C) for a period of 10 hours. The resulting reaction mixtures were partially evaporated, 100 g of t-butyl methyl ether were added, and the resulting suspensions were filtered off at 10 °C. The respective products were washed with t-butyl methyl ether and dried at 60 °C.

[0134] The following Tables 1 and 2 summarize the respective substances, any deviations from the above standard procedure, yields, and the characterization of the products obtained. Table 1: Characteristic data of acylcyanamides according to the invention and their preparation Example No. Product name Feedstock (carboxylic acid ester) Process details and yield Analytical data A-3 Sodium methoxycarbonylcyanamide CAS 51234-98-1 Dimethyl carbonate complete evaporation of the reaction suspension; Content > 98%, melting point 242.5 °C Yield 99% A-4 Sodium benzoyl cyanamide CAS 67998-88-3 Benzoic acid methyl ester Yield 76% Content 100%, melting point 295.6 °C A-5 Sodium propionyl cyanamide CAS 84945-99-3 Propionic acid methyl ester Yield 41% Content > 98%, melting point 143°C with decomposition A-6 Sodium butyrylcyanamide Butyric acid methyl ester Yield 44% Content > 98%, melting point 176-181°C A-7 Sodium isobutyrylcyanamide Isobutyric acid methyl ester Yield 57% Content > 96%, contained approx. 4% methanol, melting point 127-133°C .A-8 Sodium pivaloylcyanamide 2,2-Dimethylacetate methyl ester 72 hours response time required; Content > 98%, melting point 295-300°C Yield 70% A-9 Sodium hexanoylcyanamide Methyl hexanoate Yield 55% Content > 98%, melting point 170-174°C A-10 Sodium dodecanoyl cyanamide CAS 93238-02-9 Dodecanoic acid methyl ester Yield 82% Content > 98%, melting point 155-160°C A-11 Sodium oleylcyanamide oleic acid methyl ester 72 hours reaction time required, the product was obtained as an oil by evaporation; Content approx. 85% Quantitative yield A-12 Sodium phenylacetylcyanamide CAS 103818-57-1 Phenylacetic acid methyl ester Yield 60% Content 96%, hygroscopic, contained 4% water, melting point 183-187°C A-13 Sodium 4-methyl-benzoyl-cyanamide 4-Methylbenzoic acid methyl ester Yield 73% Content > 98%, melting point CAS 67998-89-4 340°C with decomposition A-14 Disodium (3-(Cyanamidocarbonyl)propionylcyanamide) CAS 88245-65-2 Succinic acid dimethyl ester Use 0.5 mol succinic acid dimethyl ester, 240 ml methanol; Content 92%, contained 8% sodium 3-(methoxycarbonyl)propionyl cyanamide, no melting point, decomposition from 300°C Yield 48% A-15 Disodium (5-(cyano-amidocarbonyl)-pentanoyl-cyanamide) CAS 88245-91-2 Dimethyl adipate Use 0.5 mol adipic acid dimethyl ester, 240 ml methanol; Content 96%, contained 4% sodium 5-(methoxycarbonyl)-pentanoyl-cyanamide, melting point 272-278°C with decomposition Yield 36% Table 2: NMR data of acylcyanamides according to the invention, each dissolved in d 6 -DSMO 1< H-NMR (ppm) 13< C-NMR (ppm) A-3 3,40 163,39, 122,26, 51,55 A-4 7.90 (m, 2H), 7.36 (m, 1H), 7.28 (m, 2H) 174.77, 138.48, 129.89, 128.14 (2C), 127.44 (2C), 122.86 A-5 1.94 (q), 0.89 (t) 183,59, 122,70, 31,01, 10,84 A-6 1.92 (t), 1.42 (m), 0.80 (t) 182,79, 122,70, 40,09, 19,39, 14,06 A-7 2.16 (sep), 0.92 (d) 186,96, 123,04, 36,12, 20,42 (2C) A-8 0,97 (s) 188,22, 123,49, 38,85, 28,64 (3C) A-9 1.91 (t, 2H), 1.40 (m, 2H), 1.24-1.17 (m, 4H), 0.83 (t, 3H) 182,80, 122,68, 38,03, 31,32, 25,81, 22,09, 13,98 A-10 1.90 (t, 2H), 1.39 (m, 2H), 1.24-1.19 (m, 16H), 0.84 (t, 3H) 182,63, 122,66, 38,08, 31,32, 29,10-29,06 (5C), 28,74, 26,14, 22,11, 13,95 A-11 5.30 (m, 2H), 1.97 (m, 4H), 1.89 (t, 2H), 1.38 (m, 2H), 1.29-1.22 (m, 20H), 0.83 (t, 3H) 182,49, 129,74, 129,60, 122,63, 31,30, 30,91, 29,18-28,60 (8C), 26,68, 26,61, 26,14, 22,10, 13,93 A-12 7.24-7.20(m, 4H), 7.14 (m, 1H), 3.25 (s, 2H) 180.57, 138.49, 129.19 (2C), 127.82 (2C), 125.61, 122.39, 45.30 A-13 7.79 (d, 2H), 7.09 (d, 2H), 2.28 (s, 3H) 174.85, 139.38, 135.81, 128.23 (2C), 128.04 (2C), 123.00, 20.97 A-14 2.10 (t, 4H) 182.91 (2C), 122.61 (2C), 34.92 (2C) A-15 1.89 (m, 4H), 1.35 (m, 4H) 182.85 (2C), 122.68 (2C), 38.07 (2C), 26.16 (2C) Examples of concentrate production Example B-1 Sodium acetylcyanamide as an aqueous solution with surfactant

[0135] 250 g of sodium acetylcyanamide from Example A-1 were dissolved in 600 g of water. 2.4 g of the nonionic surfactant BreakThru® OE-446 (manufacturer Evonik) were added, and the mixture was made up to a total of 1000 g with water. A clear solution was obtained. Example B-1a Sodium acetylcyanamide as an emulsifiable solution in ethanol / water / biodiesel / surfactant

[0136] 200 g of sodium acetylcyanamide from Example A-1 were dissolved in 600 g of a mixture of 80 wt% ethanol and 20 wt% water. 50 g of rapeseed oil methyl ester, 2.4 g of the nonionic surfactant BreakThru®< S-240 (manufacturer: Evonik), and 20 mg of the dye Iragon Blue ABL9-L (manufacturer: BASF) were added. The mixture was made up to 1000 g with ethanol / water. This resulted in a slightly blue, clear solution that was easily emulsifiable in water. Example B-1b Potassium acetylcyanamide as a solid

[0137] 100 g of potassium acetylcyanamide from Example A-1c was finely ground with 1 g of sodium dodecyl sulfate and 100 g of anhydrous sodium sulfate. This resulted in a white solid that was readily soluble in water with slight foaming. Example B-2 Sodium formylcyanamide as an aqueous solution with surfactant

[0138] 250 g of sodium formylcyanamide from Example A-2 were dissolved in 500 g of water, to which 2.4 g of the nonionic surfactant BreakThru ®< OE-446 and 20 mg of the dye Iragon Blue ABL9-L were added, and the solution was made up to 1000 g with water. This resulted in a clear, blue-colored concentrate solution. Example B-3 Sodium propionylcyanamide as an aqueous solution with surfactant

[0139] 250 g of sodium propionylcyanamide from Example A-2 were dissolved in 500 g of water, to which 2.4 g of the nonionic surfactant BreakThru ®< OE-446 and 20 mg of the dye Iragon Blue ABL9-L were added, and the solution was made up to 1000 g with water. This resulted in a clear, blue-colored concentrate solution. Reference example B-16 Production of a concentrate containing cyanamide

[0140] 400 g of pure cyanamide were dissolved in 600 g of water. The pH was adjusted to 4.2 with approximately 0.1 g of phosphoric acid. 10 g of BreakThru®< OE446 and 20 mg of Iragon Blue ABL9-L were added. A blue-colored concentrate solution B-16 was obtained. Storage stability of concentrate solutions B-1, B-2 and B-3 compared to B-16 (reference)

[0141] The concentrate solutions from B-1, B-2, and B-3, as well as the cyanamide-containing reference solution B-16, were stored at 60°C, and samples were taken at various intervals. These were immediately analyzed for their acylcyanamide and cyanamide content using ion chromatography. The respective starting solution, stored at -18°C, served as a reference. This was assigned a concentration of 100%, and the concentration decrease was determined relative to this concentration. Table 3: Storage stability concentrate B-1 B-2 B-3 B-16 freshly made 100% 100% 100% 100% after 1 day at 60°C 99,9% 81,6% 99,5% 98,6% after 2 days at 60°C 99,5% 66,8% 99,3% 97,4% after 4 days at 60°C 99,3% 41,7% 98,1% 90,0% after 7 days at 60°C 98,3% < 30% 97,5% 46,4% after 14 days at 60°C 95,0% < 30% 96,6% < 30%

[0142] The results show that the solutions of sodium acetylcyanamide (B-1) and sodium propionylcyanamide (B-3) exhibit significantly better stability and thus better storage life than the state-of-the-art concentrated solution of cyanamide (B-16). This is a decisive advantage for handling in agriculture. Examples of greenhouse experiments

[0143] Greenhouse experiments were conducted using cut fruit tree branches placed in glasses of water and kept under controlled conditions with temperature control at approximately 22 °C and natural light.

[0144] Branches of the following fruit tree species were used: C1: Table apple, variety Boikenapfel

[0145] Dessert apple: Malus domestica variety BoikenFirst described in 1828 in Bremen by Deichvogt Boiken. An apple variety for harsh locations and suitable for almost any soil, it requires heavy soils and not too warm locations. Tree growth is initially vigorous, later moderately vigorous. Mature crowns become broadly spherical and loosely branched. Flowering occurs medium-late and is long-lasting, with large petals and a slight pink tinge. Yields are late (October) and irregular, while maintaining long shelf life and resistance to pressure. The variety exhibits low respiration in storage and improves in quality with increasing ripeness. C2: Dessert apple, Zabergäu-Renette variety

[0146] Dessert apple: Malus domesticaThe Zabergäu-Renette variety first emerged in 1885 as a chance seedling in Hausen ad Zaber, Baden-Württemberg, and was initially known as 'Hausener Graue Renettte'. No specific site variety; it requires heavy soils (clay). Initially, the tree grows vigorously with slanting, upright leading branches, later becoming medium-vigorous with flat branches. The crown is broad and flat-rounded with flat fruiting wood. Leaves are large, broadly oval, and have a clearly defined tip. A triploid variety with late and long-lasting flowering. Yields early, medium-high, and somewhat alternate. C3: Table cherry, variety Burlat

[0147] Table cherry: Prunus aviumThe Bigarreau Burlat or Hativ Burlat variety is a vigorous, somewhat sparsely growing sweet cherry tree with horizontally branching lateral shoots. The variety has been known since 1930 and is one of the most important varieties in commercial cultivation. It blooms early, ripens early (end of May for the second cherry variety), and begins to yield late. Medium but consistent yields make it a secondary variety for early-season and dry regions. C4: Grape, Pinot Noir variety

[0148] Grape: Vitis vinifera subsp. vinifera variety. Pinot Noir is an important and highly regarded red wine variety that may have existed for 2,000 years. It is cultivated worldwide because it produces high-quality red wines and has sufficient winter frost resistance. The variety requires early and good locations with deep, warm, medium-heavy, and fertile soils with good drainage. Pinot Noir produces regular, medium to high yields. However, there are a large number of clones that differ in yield, berry size, and looseness of the berries.

[0149] The branches and shoots were cut in November, approximately one week after the last leaf fall, but before the first night frost. Branch sections were trimmed to the same length and divided into groups of five branches each, ensuring a uniform number of buds and shoot shape per group.

[0150] The test solutions were prepared directly, i.e., without intermediate preparation of a concentrate. For each of the test substances A-1 to A-13, an aqueous solution of 0.15 mol of the test substance and 0.15 g of BreakThru ®< OE-446 was prepared and made up to a total of 500 g with water. 0.075 mol of each of the bis-cyanamides A-14 and A-15 were made up to a total of 500 g in the same way. These test solutions (in conjunction with the above four species / types Cx) were assigned the test numbers Cx-A1 to Cx-A15.

[0151] The following reference solutions were used for negative and positive control: Cx-0: 500 g pure water (negative control) Cx-0a: 0.15 g BreakThru ®< OE-446, made up to 500 g with pure water (negative control) Cx-16: 0.15 mol (6.30 g) pure cyanamide and 0.15 g BreakThru ®< OE-446, made up to 500 g with water (positive control)

[0152] The test solutions (15 test solutions) were each placed in a photo dish, and five branches were immersed in the solution. If necessary, the solution was further moistened with a brush to ensure the entire surface was wetted. The branches were then placed on filter paper to allow excess liquid to drain off and allowed to dry for 20 minutes. Then, each of the five uniformly treated branches was placed in a glass of pure water and placed in the greenhouse as described above.

[0153] After specified evaluation times T1 to T6 (after 14, 16, 21, 27, 36, and 56 days, respectively, determined after application of the test solution "Day 0"), the bud development of each batch was assessed using the following rating scale: Stage 0: Buds unchanged. Stage 1: Buds slightly swollen, first green tips visible. Stage 2: Strongly swollen, green buds. Stage 3: Buds about to burst open, leaf or flower buds already visible. Stage 4: Flower buds fully developed but still closed, white petals already visible. In the case of the grapevine, stage 4 was the unfolding of the first leaves. Stage 5: Flowers fully open, or in the case of the grapevine, the unfolding of the flower buds ("apples") on the fully leafed shoots. Evaluation of the experiments

[0154] A dormancy-breaking effect is present if, depending on the species under investigation (fruit tree), the assessment level 4 is reached or exceeded after a number of n days (depending on the species (fruit tree)) compared to the negative control (water or water with surfactant). The greater the time difference and / or the assessment level compared to the negative control, the better the dormancy-breaking effect is to be classified. n (for C1, C2, C4): 36 days n (for C3): 27 days

[0155] A good dormancy-breaking effect is present if, depending on the species under test (fruit tree), the evaluation level 4 is reached or exceeded after a number of n days (depending on the species (fruit tree)) compared to the negative control (water or water with surfactant). The greater the time difference and / or the evaluation level compared to the negative control, the better the dormancy-breaking effect is to be classified. n (for C1, C2, C4): 27 days n (for C3): 21 days Table 3: Results of the apple branches C1 at the evaluation times T1 to T6: T1 / (14 days) T2 / (16 days) T3 / (21 days) T4 / (27 days) T5 / (36 days) T6 / (56 days) C1-0 0 0 0 1 1 1 C1-0a 0 0 0 1 1 1 C1-A1 0 0 2 3 5 5 C1-A2 0 0 4 5 5 5 C1-A3 1 1 2 3 4 5 C1-A4 1 1 1 2 3 4 C1-A5 2 2 4 5 5 5 C1-A6 2 3 4 5 5 5 C1-A7 2 3 4 5 5 5 C1-A8 0 0 2 4 4 4 C1-A9 0 1 1 2 2 3 C1-A10 1 2 4 5 5 5 C1-A11 0 1 2 3 5 5 C1-A12 0 1 2 2 5 5 C1-A13 0 0 0 1 4 4 C1-A14 1 1 2 3 5 5 C1-A15 0 0 1 2 3 4 C1-16 3 4 5 5 5 5

[0156] The test results show that 12 (80%) of the tested substances have a dormancy-breaking effect according to the definition given above (cf. A1, A2, A3, A5, A6, A7, A8, A10, A11, A12, A13, A14). Six (40%) of the tested substances even exhibit a good to very good dormancy-breaking effect on the tested species (cf. A2, A5, A6, A7, A8, A10). Table 4: Results of apple branches C2 at evaluation times T1 to T6 T1 / (14 days) T2 / (16 days) T3 / (21 days) T4 / (27 days) T5 / (36 days) T6 / (56 days) C2-0 0 0 0 0 0 0 C2-0a 0 0 0 1 2 3 C2-A1 0 0 1 3 5 5 C2-A2 0 0 1 3 5 5 C2-A3 0 0 0 2 4 4 C2-A4 0 0 0 1 2 2 C2-A5 0 0 0 1 3 4 C2-A6 0 0 1 2 5 5 C2-A7 0 0 1 1 5 5 C2-A8 0 0 0 1 2 4 C2-A9 0 1 4 5 5 5 C2-A10 0 0 0 1 2 4 C2-A11 0 0 3 3 4 5 C2-A12 0 0 3 3 4 5 C2-A13 0 0 1 3 3 5 C2-A14 0 0 0 1 3 4 C2-A15 0 0 1 5 5 5 C2-16 0 0 3 4 5 5

[0157] The test results show that 9 (60%) of the substances tested have a dormancy-breaking effect according to the definition given above (cf. A1, A2, A3, A6, A7, A9, A11, A12, A15). Two (13%) of the substances tested even show a good to very good dormancy-breaking effect on the species tested (cf. A9, A15). Overall result apple (C1, C2)

[0158] Depending on the apple variety tested, 14 of the 15 substances tested exhibited a dormancy-breaking effect in at least one apple variety. Of particular note are substances A6, A7, A9, and A15, which showed similar to or equal efficacy compared to the positive control. Table 5: Results of the cherry branches C3 at the evaluation times T1 to T6 T1 / (14 days) T2 / (16 days) T3 / (21 days) T4 / (27 days) T5 / (36 days) T6 / (56 days) C3-0 0 0 0 0 1 5 C3-0a 0 0 0 0 0 3 C3-A1 1 2 5 5 5 5 C3-A2 1 2 5 5 5 5 C3-A3 0 0 0 1 3 5 C3-A4 1 2 4 4 5 5 C3-A5 1 2 4 4 4 5 C3-A6 1 1 3 5 5 5 C3-A7 0 0 1 2 4 5 C3-A8 0 0 1 2 4 5 C3-A9 0 1 2 3 5 5 C3-A10 1 2 4 4 4 5 C3-A11 2 3 5 5 5 5 C3-A12 0 1 2 5 5 5 C3-A13 0 0 0 1 2 5 C3-A14 0 1 4 5 5 5 C3-A15 0 1 1 1 2 4 C3-16 2 4 5 5 5 5

[0159] The test results show that 9 (60%) of the substances tested have a dormancy-breaking effect according to the definition given above (cf. A1, A2, A4, A5, A6, A10, A11, A12, A14). 7 (47%) of the substances tested even show a good to very good dormancy-breaking effect on the cherry species tested (cf. A1, A2, A4, A5, A10, A11, A14). In contrast to the apple species (C1, C2), substance A4 shows a good dormancy-breaking effect on the cherry species. It is also worth emphasizing that substance A11 has an equivalent effect to cyanamide. Table 6: Results of the C4 vine shoots at the evaluation times T1 to T6 T1 / (14 days) T2 / (16 days) T3 / (21 days) T4 / (27 days) T5 / (36 days) T6 / (56 days) C4-0 0 0 0 0 2 5 C4-0a 0 0 0 0 1 5 C4-A1 0 0 0 1 4 5 C4-A2 0 1 3 5 5 5 C4-A3 0 0 0 1 5 5 C4-A4 0 0 0 3 5 5 C4-A5 0 0 0 1 3 5 C4-A6 0 0 0 1 2 5 C4-A7 0 0 0 2 5 5 C4-A8 0 0 0 1 4 5 C4-A9 0 0 0 2 5 5 C4-A10 0 0 0 1 2 4 C4-A11 0 0 1 3 4 5 C4-A12 0 0 1 3 4 4 C4-A13 0 0 0 1 3 5 C4-A14 0 0 0 2 4 4 C4-A15 0 0 0 1 4 5 C4-16 0 0 2 5 5 5

[0160] The test results show that 11 (73%) of the substances tested have a dormancy-breaking effect according to the definition given above (cf. A1, A2, A3, A4, A7, A8, A9, A11, A12, A14, A15). One (7%) of the substances tested even shows a good to very good dormancy-breaking effect on the tested species, wine (cf. A2). It is worth emphasizing that substance A2 has an equivalent effect to cyanamide. Overall result

[0161] A summary of the results on the four fruit tree species C1 to C4 shows that the sodium acylcyanamides A1 to A15 according to the invention all exhibit a more or less strong dormancy-breaking effect compared to the water reference (negative control). The effect is similar, but in some cases somewhat weaker or slightly delayed compared to the positive reference cyanamide (= standard agent according to the state of the art), whose efficacy is partially achieved depending on the species. Examples for the production of spray mixtures from concentrates Example D-1 Preparation of a spray mixture containing sodium acetylcyanamide

[0162] Ten parts of the concentrate solution from Example B-1 were diluted with 90 parts of water. This resulted in a water-clear solution, which was used as a spray mixture. The spray mixture contained approximately 0.24 mol of the active ingredient acetylcyanamide per liter. Example D-1a Preparation of a spray emulsion containing sodium acetylcyanamide

[0163] Eight parts of the concentrate solution from Example B-1a were added to 92 parts of water. The two components mixed to form a bluish, slightly cloudy emulsion. The spray mixture contained approximately 0.15 mol of acetylcyanamide per liter. Reference example D-18 Preparation of a spray mixture containing cyanamide

[0164] 2.5 parts of the concentrate solution from Example B-18 were mixed with 97.5 parts of water to obtain reference spray mixture D-18. The spray mixture contained approximately 0.24 mol of the active ingredient cyanamide per liter. Field trials Example E1: Table grapes USA

[0165] Three sections of a commercial table grape crop near Madera, California, were treated with the following spray mixtures during the dormancy phase 45 days before natural bud break (February 11): E1-0: 600 liters per hectare of water with an addition of 0.1% BreakThru ®< OE-446 E1-1: 600 liters per hectare of the spray mixture from example D-1 E1-18: 600 liters per hectare of the spray mixture from example D-18 This ensured that the vine shoots were evenly moistened.

[0166] On the 30th and 41st day after application, bud growth was counted.

[0167] Sprouting means the number of buds that have developed at least one leaf after n days, relative to the total number of buds on the shoots at time n=0 days (day of application of the spray solution). Table 7: Results Table Grapes USA 30 days 41 days E1-0 (zero reference) 42.5% bud break 76.3% bud break E1-1 (Invention) 50.5% bud break 74.0% bud break E1-18 (comparison) 55.8% bud break 77.5% bud break

[0168] After 30 days, bud break was significantly premature due to the treatment, with the inventive treatment E1-1 not being quite as effective as the state-of-the-art cyanamide treatment (E1-18). Due to the specific weather conditions, the advantage achieved by both active ingredient treatments was lost after 41 days. Example E2: Table grapes Spain

[0169] Three sections of a table grape crop in southern Spain (variety Red Globe) were treated with the following spray mixtures during the dormancy phase 45 days before natural bud break (February 5): E2-0: 600 liters per hectare of water with an addition of 0.1% BreakThru ®< OE-446 E2-1: 600 liters per hectare of the spray mixture from example D-1 E2-18: 600 liters per hectare of the spray mixture from example D-18

[0170] This ensured that the vine shoots were evenly moistened.

[0171] On April 3, bud break was recorded.

[0172] Sprouting means the number of buds that have developed at least one leaf after n days, relative to the total number of buds on the shoots at time n=0 days (day of application of the spray solution). Table 8: Results of table grapes in Spain E2-0 (zero reference) 73.8% bud break E2-1 (Invention) 86.7% bud break E2-18 (comparison) 86.0% bud break

[0173] The treatment with sodium acetylcyanamide according to the invention is therefore as effective as the state of the art treatment with cyanamide. Example E3: Table grapes India

[0174] Three sections of a table grape crop in India with the varieties Bordon AR and Hammar AR were treated with the following spray mixtures during the dormancy phase: E3-0: 600 liters per hectare of water with an addition of 0.1% BreakThru ®< OE-446 E3-1: 600 liters per hectare of the spray mixture from example D-1 E3-18: 600 liters per hectare of the spray mixture from example D-18

[0175] This ensured that the vine shoots were evenly moistened.

[0176] After 30 and 45 days, bud break was recorded. Bud break refers to the number of buds that have developed at least one leaf after n days, relative to the total number of buds on the shoots at n = 0 days (the day of spray application). Table 9: Results Table Grapes India Variety Bordon AR Variety Hammar AR Evaluation time 30 days 45 days 30 days 45 days E3-0 (zero reference) 33.1% bud break 58.6% bud break 10.0% bud break 71.2% bud break E3-1 (Invention) 36.6% bud break 66.8% bud break 18.0% bud break 81.3% bud break E3-18 (comparison) 36.1% bud break 68.1% bud break 15.3% bud break 81.0% bud break

[0177] The treatment with sodium acetylcyanamide according to the invention is therefore at least as effective as the state of the art treatment with cyanamide.

Claims

1. Use of at least one compound from the group of acylcyanamides or a salt thereof according to formula (I) or formula (II) for regulating the generative growth of plants or for breaking the dormancy of fruit trees, wherein the following applies to formula (I) and formula (II) wherein radicals R1, R2, R3, R4, R5 and cations M1, M2 independently of one another mean: R1 = hydrogen, C1 to C20 alkyl, C3 to C12 cycloalkyl, C2 to C20 alkenyl, C1 to C20 alkoxy, aryl, alkylaryl or arylalkyl, or a radical Q, wherein Q is: Q = C1 to C20 alkyl, C3 to C12 cycloalkyl, C2 to C20 alkenyl, C1 to C20 alkoxy, aryl, alkylaryl or arylalkyl, each substituted by a radical of formula (III) or formula (IV) M1, M2 = independently of one another Li, Na, K, ½Ca, ½Mg, or NR2R3R4R5, R2, R3, R4, R5 = independently of one another hydrogen or C1 to C20 alkyl.

2. Use according to claim 1, characterized in that at least one compound from the group of acylcyanamides or a salt thereof according to formula (I) or formula (II) is used, wherein radicals R1, R2, R3, R4, R5 and cations M1, M2 independently of one another mean: R1 = hydrogen, C1 to C20 alkyl, C3 to C12 cycloalkyl, C2 to C20 alkenyl, C1 to C20 alkoxy or a radical Q, wherein Q is: Q = C1 to C20 alkyl, C3 to C12 cycloalkyl, C2 to C20 alkenyl, C1 to C20 alkoxy, each substituted by a radical of formula (III) or formula (IV), M1, M2 = independently of one another Li, Na, K, ½Ca, ½Mg, or NR2R3R4R5, R2, R3, R4, R5 = independently of one another hydrogen or C1 to C20 alkyl.

3. Use according to claim 1, characterized in that at least one compound from the group of acylcyanamides or a salt thereof according to formula (I) or formula (II) is used, wherein radicals R1, R2, R3, R4, R5 and cations M1, M2 independently of one another mean: R1 = aryl, alkylaryl or arylalkyl, or a radical Q, wherein Q is: Q = aryl, alkylaryl or arylalkyl, each substituted by a radical of formula (III) or formula (IV), M1, M2 = independently of one another Li, Na, K, ½Ca, ½Mg, or NR2R3R4R5, R2, R3, R4, R5 = independently of one another hydrogen or C1 to C20 alkyl.

4. Use according to claim 1 or 2, characterized in that at least one compound from the group of acylcyanamides or a salt thereof according to formula (I) or formula (II) is used, wherein radical R1 and cations M1, M2 independently of one another mean: R1 = hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, n-pentyl, n-hexyl, n-heptyl, n-octyl or a radical Q, wherein Q is: Q = methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, each substituted by a radical of formula (III) or formula (IV), M1, M2 = independently of one another Na or K.

5. Use according to at least one of the preceding claims, characterized in that at least one compound selected from the group consisting of sodium formylcyanamide, sodium acetylcyanamide, sodium propionylcyanamide, sodium n-butyrylcyanamide, sodium isobutyrylcyanamide, sodium methoxycarbonylcyanamide, sodium ethoxycarbonylcyanamide, potassium formylcyanamide, potassium acetylcyanamide, potassium propionylcyanamide, potassium n-butyrylcyanamide, potassium isobutyrylcyanamide, potassium methoxycarbonylcyanamide or potassium ethoxycarbonylcyanamide is used.

6. Use according to at least one of the preceding claims, characterized in that as plants, as crops and cultivated plants or as fruit trees, plants selected from the group consisting of grape (Vitis vinifera), kiwi (Actinidia deliciosa, Actinidia chinensis, or Actinidia arguta), blueberry (Vaccinium myrtillus, Vaccinium corymbosum, Vaccinium virgatum, Vaccinium angustifolium or Vaccinium myrtilloides), cherry (Prunus avium or Prunus cerasus), plum or damson (Prunus domestica), apple (Malus domestica or Malus orientalis), pear (Pyrus communis, Pyrus pyraster or Pyrus pyrifolia), quince (Cydonia oblonga), peach (Prunus persica), apricot (Prunus armeniaca), raspberry (Rubus idaeus), persimmon (Diospyrus kaki), fig (Ficus carica) or their cross products or cultivars are treated.

7. Plant growth regulator concentrate for regulating the generative growth of plants or for breaking the dormancy of fruit trees comprising a) at least one active ingredient from the group of acylcyanamides or a salt thereof according to formula (I) or formula (II), wherein the following applies to formula (I) and formula (II): wherein radicals R1, R2, R3, R4, R5 and cations M1, M2 independently of one another mean: R1 = hydrogen, C1 to C20 alkyl, C3 to C12 cycloalkyl, C2 to C20 alkenyl, C1 to C20 alkoxy, aryl, alkylaryl or arylalkyl, or a radical Q, wherein Q is: Q = C1 to C20 alkyl, C3 to C12 cycloalkyl, C2 to C20 alkenyl, C1 to C20 alkoxy, aryl, alkylaryl or arylalkyl, each substituted by a radical of formula (III) or formula (IV) M1, M2 = independently of one another Li, Na, K, ½Ca, ½Mg, or NR2R3R4R5, R2, R3, R4, R5 = independently of one another hydrogen or C1 to C20 alkyl, b) at least one additive from the group of solvents, oils, surfactants or emulsifiers that is safe or approved for agricultural purposes, wherein the concentrate having a concentration of active ingredient according to a) in the range of 200 to 600 g / l.

8. Plant growth regulator concentrate for regulating the generative growth of plants or for breaking the dormancy of fruit trees comprising a) at least one active ingredient from the group of acylcyanamides or a salt thereof according to formula (I) or formula (II), wherein the following applies to formula (I) and formula (II): wherein radicals R1, R2, R3, R4, R5 and cations M1, M2 independently of one another mean: R1 = hydrogen, an alkyl radical selected from the group methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, 2-ethylpropyl or n-hexyl, an alkylene radical selected from the group ethenyl, propenyl, butenyl, pentenyl, hexenyl, butadienyl, pentadienyl, hexadienyl or hexatrienyl, C3 to C12 cycloalkyl, C1 to C20 alkoxy, aryl, alkylaryl or arylalkyl, or a radical Q, wherein Q is: Q = C1 to C20 alkyl, C3 to C12 cycloalkyl, C2 to C20 alkenyl, C1 to C20 alkoxy, aryl, alkylaryl or arylalkyl, each substituted by a radical of formula (III) or formula (IV) M1, M2 = independently of one another Li, Na, K, ½Ca, ½Mg, or NR2R3R4R5, R2, R3, R4, R5 = independently of one another hydrogen or C1 to C20 alkyl, b) at least one additive from the group of solvents, oils, surfactants or emulsifiers that is safe or approved for agricultural purposes, wherein the concentrate having a concentration of active ingredient according to a) in the range of 100 to 600 g / l.

9. Plant growth regulator concentrate according to claim 7, characterized in that the concentrate a) comprises at least one active ingredient selected from the group consisting of acylcyanamides or a salt thereof according to formula (I) or formula (II), wherein radicals R1, R2, R3, R4, R5 and cations M1, M2 independently of one another mean: R1 = hydrogen, C1 to C20 alkyl, C3 to C12 cycloalkyl, C2 to C20 alkenyl, C1 to C20 alkoxy or a radical Q, wherein Q is: Q = C1 to C20 alkyl, C3 to C12 cycloalkyl, C2 to C20 alkenyl, C1 to C20 alkoxy, each substituted by a radical of formula (III) or formula (IV), M1, M2 = independently of one another Li, Na, K, ½Ca, ½Mg, or NR2R3R4R5, R2, R3, R4, R5 = independently of one another hydrogen or C1 to C20 alkyl.

10. Plant growth regulator concentrate according to at least one of the preceding claims 7 to 9, characterized in that the concentrate is a solution, an emulsion or an emulsifiable solution comprising as solvent a solvent selected from the group consisting of water, ethanol, isopropanol, glycol, polyglycol, glycerol or mixtures of these solvents.

11. Plant growth regulator concentrate according to at least one of the preceding claims 7 to 10, characterized in that the concentrate is a solution, an emulsion or an emulsifiable solution comprising as oil an oil from the group of plant oils.

12. Plant growth regulator concentrate according to at least one of the preceding claims 7 to 11, characterized in that the concentrate is a solution, an emulsion or an emulsifiable solution comprising as surfactant a surfactant selected from the group consisting of nonionic surfactants.

13. Plant growth regulator concentrate according to at least one of the preceding claims 7 to 12, characterized in that the concentrate comprises as surfactant a surfactant containing one or more compounds selected from the group consisting of ethoxylates according to formula (VII), fatty alcohol glucosides according to formula (VIII), or mixtures thereof, wherein the following applies to formula (VII) and formula (VIII),         R11-O- (CH2CH2O)n-H     Formula (VII) wherein radicals R11, R12 and indices n, m simultaneously or independently mean: R11 = a linear or branched alkyl or alkenyl group having 6 to 24 carbon atoms, a partially or fully fluorinated alkyl group having 6 to 18 carbon atoms, a phenyl group, an alkyl-substituted phenyl group, a mono- or polyfunctional siloxane group, R12 = a linear or branched alkyl or alkenyl group containing 6 to 24 carbon atoms, n = a number from 2 to 20, m = a number from 1 to 5.

14. Plant growth regulator concentrate according to at least one of the preceding claims 7 to 13, characterized in that the concentrate is a solution, an emulsion or an emulsifiable solution comprising as emulsifier an emulsifier selected from the group consisting of nonionic oil-in-water emulsifiers.

15. Plant growth regulator concentrate according to at least one of the preceding claims 7 to 14, characterized in that the concentrate further comprises at least one formulation adjuvant approved for agricultural use selected from the group consisting of pH regulators, colorants, thickeners, dispersants, solubilizers, viscosity modifiers, labeling agents and bittering agents.

16. Plant growth regulator concentrate according to claim 8, characterized in that the concentrate comprises: a) at least one active ingredient from the group consisting of sodium formylcyanamide, sodium acetylcyanamide, sodium propionylcyanamide, sodium n-butyrylcyanamide, sodium isobutyrylcyanamide, sodium methoxycarbonylcyanamide, sodium ethoxycarbonylcyanamide, potassium formylcyanamide, potassium acetylcyanamide, potassium propionylcyanamide, potassium n-butyrylcyanamide, potassium isobutyrylcyanamide, potassium methoxycarbonylcyanamide or potassium ethoxycarbonylcyanamide, b) at least one additive from the group of solvents that is safe or approved for agricultural purposes, and c) at least one additive from the group of oils, surfactants or emulsifiers that is safe or approved for agricultural purposes, wherein the concentrate having a concentration of active ingredient in the range of 100 to 600 g / l.

17. A method for regulating the generative growth of plants or for breaking the dormancy of fruit trees comprising application by dipping, brushing or spraying of the branches, sprouts or buds of the plants with an aqueous solution comprising at least one active ingredient from the group of acylcyanamides or a salt thereof according to formula (I) or formula (II), during dormancy of the plants, wherein the following applies to formula (I) and formula (II) wherein radicals R1, R2, R3, R4, R5 and cations M1, M2 independently of one another mean: R1 = hydrogen, C1 to C20 alkyl, C3 to C12 cycloalkyl, C2 to C20 alkenyl, C1 to C20 alkoxy, aryl, alkylaryl or arylalkyl, or a radical Q, wherein Q is: Q = C1 to C20 alkyl, C3 to C12 cycloalkyl, C2 to C20 alkenyl, C1 to C20 alkoxy, aryl, alkylaryl or arylalkyl, each substituted by a radical of formula (III) or formula (IV) M1, M2 = independently of one another Li, Na, K, ½Ca, ½Mg, or NR2R3R4R5, R2, R3, R4, R5 = independently of one another hydrogen or C1 to C20 alkyl.