Use of acylcyanamides or their salts for regulating plant growth - Patents.com

Abstract

The present invention relates to the use of an acylcyanamide or a salt thereof as an active ingredient of a plant growth regulator, particularly for breaking dormancy in fruit trees.

Description

[Technical field]

[0001] The present invention relates to the use of an acylcyanamide or a salt thereof as an active ingredient of a plant growth regulator, particularly for breaking dormancy in fruit trees. [Background technology]

[0002] Plant growth regulators are active ingredients that specifically affect the growth, development, and metabolic processes of agricultural crops and cultivated plants, even when applied in minimal doses. The term "plant growth regulators" includes both natural plant hormones and synthetic substances. Plant growth regulators are used in the production of agricultural plants to reduce or prevent the negative effects of many environmental factors, or to enhance their positive effects. The use of plant growth regulators can increase the yield potential of agricultural crops and cultivated plants, make more extensive use of site factors, and ensure the effectiveness of intensification measures.

[0003] Dormancy is the term for a resting period in the development and life cycle of plants, which can extend to the buds (Knospen) and seeds, and is characterized by the absence of plant growth. Dormancy can be aborted or broken by light, temperature, or moisture. For example, the so-called breaking of dormancy is induced in many seeds by species-specific cold periods ("stratification"). In a similar way, i.e. by the effects of cold or frost, the dormancy of the buds is also ended, whereby in both cases changes in the concentration of the plant hormones abscisic acid, auxin and gibberellin can be observed. These natural dormant periods are important for plant physiology, since premature germination in the event of a subsequent cold period can lead to freezing and possible death of the newly formed plant parts.

[0004] Breaking dormancy, especially bud dormancy, can also be induced by the effect of plant growth regulators applied to the plant by topical application.For example, cyanamide has long been known as an active ingredient for breaking dormancy, especially in fresh fruit.The corresponding application is described, for example, in DE 3150404 and ZA 8302332.Further description of the use of cyanamide-containing spray mixtures for breaking dormancy 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, - Kiwifruit: CCNee, New Zealand Journal of Crop and Horticultural Science (1991), 19, 419, - Peach: J.H. Siller-Cepeda, HortScience (1992), 27, 874.

[0005] Artificial dormancy breaking, initiated by the application of suitable active ingredients, is particularly economically valuable, since it allows the harvest to be shifted to an earlier time than natural and thus obtain a higher price for the fruit. For the cultivation of plants in tropical regions (such as grapes or cherries), the artificial breaking of dormancy and thus the deliberate and calculated triggering of bud germination is essential, since these plants rarely germinate naturally in tropical environments and only germinate very unevenly. In this respect, treatment with agents that break dormancy is essential, for example, for the cultivation of table grapes or cherries in tropical mountainous regions and thus for supplying the world market in the off-season in temperate latitudes of the Northern or Southern Hemisphere.

[0006] Cyanamide for use as a dormancy-breaking spray mixture is usually sold as an aqueous solution, e.g. with a cyanamide content of 50% and which may further contain additives such as stabilizers, dyes, surfactants, etc. Alternatively, organic oil-containing concentrates based on cyanamide are described in DE 102014003082 A1, which show improved dormancy-breaking effect after dilution with water.

[0007] In addition to the desired dormancy-breaking effect in plants, cyanamide unfortunately produces various physiological effects in animals and humans. For example, cyanamide is classified as highly corrosive (destroys the skin), acutely toxic, and teratogenic. Further investigations show that special occupational safety measures must be observed when using cyanamide or cyanamide-containing solutions in agricultural applications.

[0008] Cyanamide is also a polymeric 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 for preparing cyanamide-containing spray mixtures are already subject to decomposition or dimerization with the formation of cyanoguanidine at normal storage temperatures and therefore only have a time-limited effectiveness. Summary of the Invention [Problem to be solved by the invention]

[0009] 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, can be classified as safe on the basis of its components and can be evaluated as efficient in terms of its effectiveness. [Means for solving the problem]

[0010] These problems are solved by the use according to claim 1, the concentrate according to claim 7 and the method according to claim 15. Preferred embodiments of the invention are set out in the dependent claims, which can be combined in any way with one another. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0011] A first embodiment of the invention is therefore the use of at least one compound from the group of the acylcyanamides of formula (I) or (II) or their salts for regulating the reproductive growth of plants, in particular the reproductive growth of agricultural crops and cultivated plants, preferably the reproductive growth of fruit trees, or for breaking dormancy in fruit trees, in which the following applies to formula (I) and formula (II):

[0012] [ka]

[0013] [ka]

[0014] In the formula, R 1 , R 2 , R 3 , R 4 , R 5 Group and cation M 1 , M 2 means, independently of each other: R 1 = Hydrogen, C1-C 20 Alkyl, C3-C 12 Cycloalkyl, C2-C 20 Alkenyl, C1-C 20 an alkoxy, aryl, alkylaryl or arylalkyl, or Q group, where Q is: Q=C1-C, each of which is substituted with a group of formula (III) or formula (IV). 20 Alkyl, C3-C 12 Cycloalkyl, C2-C 20 Alkenyl, C1-C 20alkoxy, aryl, alkylaryl or arylalkyl;

[0015] [ka]

[0016] [ka]

[0017] M 1 , M 2 = Li, Na, K, 1 / 2Ca, 1 / 2Mg, or NR, independently of each other 2 R 3 R 4 R 5 and R 2 , R 3 , R 4 , R 5 = independently of each other hydrogen or C1-C 20 It is an alkyl.

[0018] According to the present invention, R 1 The group is hydrogen, C1-C 20 Alkyl, C3-C 12 Cycloalkyl, C2-C 20 Alkenyl, C1-C 20 It can be an alkoxy, aryl, alkylaryl, arylalkyl or Q group, where Q is a C-C 20 Alkyl, C3-C 12 Cycloalkyl, C2-C 20 Alkenyl, C1-C 20 alkoxy, aryl, alkylaryl or arylalkyl groups, which in turn are substituted by a group of formula (III) or formula (IV).

[0019] In the context of the present invention, C1 to C 20 Alkyl is to be understood as a saturated, linear or branched aliphatic radical having a chain length of 1 to 20 carbon atoms, in particular 1 to 8 carbon atoms, and in particular of the general formula C nH 2n+1 (wherein n=an integer from 1 to 20, preferably an integer from 1 to 12, in particular an integer from 1 to 8). 20 Alkyl is preferably defined as meaning 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.

[0020] According to the present invention, C1 to C 20 Alkyl particularly preferably denotes methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, n-pentyl or n-hexyl. Very preferably, C1-C 20 Alkyl means according to the invention methyl, ethyl, n-propyl, n-butyl, n-pentyl or n-hexyl.

[0021] In the context of the present invention, C3-C 12 Cycloalkyl further means a saturated monocyclic or bicyclic aliphatic radical having 3 to 12 carbon atoms, in particular of the general formula C n H 2n-1 (wherein n=an integer from 3 to 12). 12 It is preferably defined that cycloalkyl means in particular cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl, which cycloalkyl groups in turn can be mono- or polysubstituted, further preferably by alkyl. According to the present invention, C3 to C 12 Cycloalkyl particularly preferably denotes cyclopentyl or cyclohexyl.

[0022] Furthermore, in the context of the present invention, alkanediyl refers to an alkanediyl having two binding sites and in particular 1 to 20 carbon atoms (C 20 alkanediyl), preferably having 1 to 12 carbon atoms (C 12 alkanediyl), in particular having a chain length of 1 to 6 carbon atoms (C1-C6 alkanediyl) and in particular having the general formula C n H 2n where n=an integer from 1 to 12, in particular an integer from 1 to 6.

[0023] According to the invention, alkanediyl particularly preferably means methanediyl, ethane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, petan-1,5-diyl or hexane-1,6-diyl.

[0024] Furthermore, in the context of the present invention, C2 to C 20 Alkenyl is to be understood as an unsaturated, linear or branched aliphatic radical having a chain length of 2 to 20 carbon atoms and having one, two, three or four double bonds, depending in particular on the number of double bonds, in which case one double bond is a C n H 2n-1 (n = an integer from 2 to 20), with two double bonds, C n H 2n-3 (n = an integer from 4 to 20), and C for three double bonds. n H 2n-5 (n = an integer between 6 and 20), or C for 4 double bonds n H 2n-7 (n=an integer from 8 to 20). 20It is preferably defined that 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, hexatrienyl, heptatrienyl, octatrienyl, nonatrienyl or decatrienyl, which alkenyl groups may further preferably be unbranched or may in turn be mono- or polysubstituted by alkyl.

[0025] According to the present invention, C2 to C 20 Alkenyl particularly preferably denotes heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl or octadecenyl. Very preferably, C2-C 20 Alkenyl means tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl or octadecenyl.

[0026] According to the present invention, C1 to C 20 Alkoxy means a radical of the formula -O-alkyl, in which the binding site is on the oxygen and alkyl is a C1-C alkyl radical as defined above. 20 It is preferably an alkyl group. 1 The group or Q is C1-C 12 It is an alkoxy, more preferably a C1 to C6 alkoxy.

[0027] According to the present invention, C1 to C 20 Alkoxy particularly preferably denotes methoxy, ethoxy, n-propoxy, n-butoxy or n-pentoxy. Very preferably, C1-C 20 Alkyl means according to the invention methoxy or ethoxy.

[0028] According to the invention, aryl means an aromatic group, in particular having 6 to 20 carbon atoms, preferably 6 to 10 carbon atoms, particularly preferably 6 carbon atoms, which may be monocyclic, bicyclic or polycyclic. Aryl can therefore mean, according to the invention, in particular phenyl, naphthyl, anthryl, phenanthryl, pyrenyl or perylenyl. According to the invention, aryl particularly preferably means phenyl.

[0029] According to the invention, arylalkyl means an alkyl group as defined above substituted with an aryl group as defined above, the attachment site of the arylalkyl group being located on the alkyl group. Thus, according to the invention, arylalkyl can in particular mean benzyl, 1-phenylethyl or 1-methyl-1-phenylethyl. According to the invention, arylalkyl particularly preferably means benzyl.

[0030] According to the invention, alkylaryl means an aryl group as defined above, which is in turn mono- or polysubstituted by alkyl groups as defined above, and the bonding site of the alkylaryl group is located on the aryl group. Alkylaryl can therefore mean, according to the invention, in particular tolyl, xylyl, pseudocumyl or mesityl. According to the invention, alkylaryl particularly preferably means tolyl.

[0031] Surprisingly, it has been shown that the acylcyanamides of formula (I) or formula (II) or their salts according to the invention have an effect as plant growth regulators. This fact is even more surprising, since these substances have been known per se for some time (see DE 32022013). However, until now, these acylcyanamides have only been attributed to their effect as surfactants (see DE 708428) or as accelerators for the anaerobic curing of adhesives (DE 3003437). Their effect on living plants is unknown. What is known is that cyanamide itself is rapidly and completely metabolized in humans and other vertebrates to acetylcyanamide and is thus detoxified (see FN Shirota et. al., Drug Metabolism and Disposition (1984), 12, 337 and B. Mertschenk et. al, Archives of Toxicology (1991), 65, 268). Thus, acetylcyanamide can be quantified since it is excreted from the organism via human urine (see DE 3827449). Thus, without being bound by theory, acylcyanamide should have an effect on plants that is different from the detoxification mechanisms of vertebrates. The fact that the acylcyanamides of the present invention, especially acetylcyanamide, are not "detoxified" even in plants and therefore ineffective, but have a dormancy-breaking effect, represents a completely surprising effect and the true essence of the present invention.

[0032] The dormancy-breaking effect occurs when the plant's bud burst and / or flowering occurs earlier than the plant's natural bud burst and flowering. Thus, dormancy-breaking regulates the reproductive growth of the plant. In this context, it is desirable for plants, particularly agricultural and cultivated plants or fruit trees, to fully germinate and flower in a relatively short period of time, so that the further development stage of the treated plant can be predicted. According to the present invention, such dormancy-breaking effect has been observed with acylcyanamide of formula (I) or formula (II) (see examples).

[0033] Thus, the use of acylcyanamides of formula (I) or formula (II) or their salts according to the invention makes it possible to regulate the reproductive growth of plants, in particular the reproductive growth of agricultural crops and cultivated plants, preferably the reproductive growth of fruit trees, or to break dormancy in fruit trees.

[0034] Furthermore, the acylcyanamides of the present invention have positive properties for use in agriculture.Compared to cyanamides, these compounds are stable in storage and are considered to be largely soluble in liquids.In contrast to cyanamides, these acylcyanamides have also been shown not to be subject to decomposition and / or dimerization tendency in aqueous solution.

[0035] The acylcyanamides of formula (I) according to the invention are weak NH acids, and thus they are capable of forming stable salts of formula (II) with bases, which have a neutral pH, are physiologically well tolerated, are stable during storage, and, surprisingly, are active as dormancy-breaking agents.

[0036] Thus, the acylcyanamides of formula (I) or formula (II) and their salts are ideally suited to replace cyanamide in fields of application where cyanamide cannot or should not be used due to its toxicological or other properties.

[0037] In accordance with the present invention, R 1 The group is hydrogen, C1-C 20 Alkyl, C3-C 12 Cycloalkyl, C2-C 20 Alkenyl, C1-C 20 a radical from the group consisting of alkoxy, aryl, alkylaryl or arylalkyl, or a radical Q, which is substituted with a radical of formula (III) or formula (IV), respectively; 20 Alkyl, C3-C 12 Cycloalkyl, C2-C 20 Alkenyl, C1-C 20An acylcyanamide of formula (I) or formula (II) or a salt thereof may be used, which is a radical from the group consisting of alkoxy, aryl, alkylaryl or arylalkyl.

[0038] Preferably, R 1 The group is hydrogen, C1-C 20 Alkyl, C3-C 12 Cycloalkyl, C2-C 20 Alkenyl, C1-C 20 C1-C alkyl groups selected from the group consisting of alkoxy and Q groups, Q being substituted with a group of formula (III) or formula (IV), 20 Alkyl, C3-C 12 Cycloalkyl, C2-C 20 Alkenyl, C1-C 20 An acylcyanamide or a salt thereof corresponding to formula (I) or formula (II) may be used, which is a group from the group consisting of alkoxy.

[0039] More preferably, R 1 The group is hydrogen, C1-C 20 Alkyl, C2-C 20 Alkenyl, C1-C 20 C1-C alkyl groups selected from the group consisting of alkoxy and Q groups, Q being substituted with a group of formula (III) or formula (IV), 20 Alkyl, C2-C 20 Alkenyl, C1-C 20 An acylcyanamide or a salt thereof corresponding to formula (I) or formula (II) may be used, which is a group from the group consisting of alkoxy.

[0040] Even more preferably, R 1 The group is hydrogen, C1-C 20 Alkyl, C2-C 20 alkenyl or Q groups, Q being substituted with a group of formula (III) or formula (IV), 20 Alkyl, C2-C 20 An acylcyanamide of formula (I) or formula (II) or a salt thereof may be used, which is a radical from the group consisting of alkenyl.

[0041] Particularly preferably, R 1 The group is hydrogen, C1-C 20 a radical from the group consisting of alkyl or Q radicals, Q being substituted by a radical of formula (III) or formula (IV) 20 An acylcyanamide of formula (I) or formula (II) or a salt thereof may be used, wherein the radical is from the group consisting of alkyl.

[0042] The free acid of the acylcyanamide according to the invention provides a solution with a pH similar to that of an acetic acid solution. Such an acidic solution is only suitable for special agricultural applications. Therefore, according to the invention, the salt of the acylcyanamide of formula (II) is preferred.

[0043] With respect to the variation of the cation, alkali metal and alkaline earth metal salts have been shown to form stable salts of the acylcyanamides according to the invention. Therefore, preferred are the cations M 1 and M. 2 are, independently of one another, Li, Na, K, 1 / 2Ca or 1 / 2Mg. More preferred are the alkali metal salts. Thus, M 1 and M. 2 independently of one another preferably denote Li, Na or K, very particularly preferably Na or K.

[0044] Therefore, preferably according to the invention, for regulating the reproductive growth of plants, in particular the reproductive growth of agricultural crops and cultivated plants, preferably the reproductive growth of fruit trees or for breaking dormancy in fruit trees, R 1 , R 2 , R 3 , R 4 , R 5 Group and cation M 1 , M 2 means, independently of each other: R 1 = Hydrogen, C1-C 20 Alkyl, C3-C 12 Cycloalkyl, C2-C20 Alkenyl, C1-C 20 an alkoxy or Q group, where Q is: Q=C1-C, each of which is substituted with a group of formula (III) or formula (IV). 20 Alkyl, C3-C 12 Cycloalkyl, C2-C 20 Alkenyl, C1-C 20 is an alkoxy; M 1 , M 2 = Li, Na, K, 1 / 2Ca, 1 / 2Mg, or NR, independently of each other 2 R 3 R 4 R 5 and R 2 , R 3 , R 4 , R 5 = independently of each other hydrogen or C1-C 20 is alkyl, At least one compound selected from the group consisting of acylcyanamides of formula (I) or formula (II) or salts thereof can be used.

[0045] Further preferred herein are R 1 , R 2 , R 3 , R 4 , R 5 Group and cation M 1 , M 2 means, independently of each other: R 1 = Hydrogen, C1-C 20 Alkyl, C2-C 20 Alkenyl, or C1-C 20 is an alkoxy; M 1 , M 2 = Li, Na, K, 1 / 2Ca, 1 / 2Mg, or NR, independently of each other 2 R 3 R 4 R 5 and R 2 , R 3, R 4 , R 5 = independently of each other hydrogen or C1-C 20 is alkyl, It is a compound from the group of acylcyanamides of formula (I) or (II) or a salt thereof.

[0046] Further preferred herein are R 1 Group and cation M 1 , M 2 means, independently of each other: R 1 = Hydrogen, C1-C 20 Alkyl or C1-C 20 is an alkoxy; M 1 , M 2 = independently of each other Li, Na, K, 1 / 2Ca or 1 / 2Mg, It is a compound from the group of acylcyanamides of formula (I) or (II) or a salt thereof.

[0047] More preferably, according to the present invention, R 1 Group and cation M 1 , M 2 means, independently of each other: R 1 = hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, n-pentyl, n-hexyl, n-heptyl, n-octyl or Q group, where Q is: Q=methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, each of which is substituted with a group of formula (III) or formula (IV); M 1 , M 2 = independently of each other Na or K, At least one compound selected from the group consisting of acylcyanamides of formula (I) or formula (II) or salts thereof may be used.

[0048] Particularly preferably, according to the invention, 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, potassium ethoxycarbonylcyanamide may be used.

[0049] Alternatively and preferably according to the invention R 1 , R 2 , R 3 , R 4 , R 5 Group and cation M 1 , M 2 means, independently of each other: R 1 = hydrogen, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl or a group of formula (V) or formula (VI),

[0050] [ka]

[0051] [ka]

[0052] In the formula (V) and the formula (VI), X has the following meaning: X = alkanediyl, especially C1-C 20 It is an alkanediyl, M 1 , M 2 = Li, Na, K, 1 / 2Ca, 1 / 2Mg, or NR, independently of each other2 R 3 R 4 R 5 and R 2 , R 3 , R 4 , R 5 = independently of each other hydrogen or C1-C 20 is alkyl, At least one compound selected from the group consisting of acylcyanamides of formula (I) or formula (II) or salts thereof may be used.

[0053] Alternatively and preferably according to the invention R 1 , R 2 , R 3 , R 4 , R 5 Groups and cations M 1 , M 2 means, independently of each other: R 1 = an aryl, alkylaryl or arylalkyl, or Q group, where Q is: Q=aryl, alkylaryl, or arylalkyl, each substituted with a group of formula (III) or formula (IV); M 1 , M 2 = Li, Na, K, 1 / 2Ca, 1 / 2Mg, or NR, independently of each other 2 R 3 R 4 R 5 and R 2 , R 3 , R 4 , R 5 = independently of each other hydrogen or C1-C 20 is alkyl, At least one compound selected from the group consisting of acylcyanamides of formula (I) or formula (II) or salts thereof may also be used.

[0054] According to the present invention, the acylcyanamides of formula (I) or (II) can be used to regulate the reproductive growth of plants, in particular the reproductive growth of agricultural crops and cultivated plants, preferably the reproductive growth of fruit trees, or to break dormancy in fruit trees.

[0055] In this context, reproductive growth of a plant should be understood to mean the growth of a plant characterized by the formation of sexual characteristics such as flowers, seeds, fruits or plant parts that are primarily used for reproduction. Regulation of reproductive growth can occur in different plant species by different factors such as photoperiod, chilling period or drought stress. A direct transition from dormancy to reproductive growth can also be induced.

[0056] Furthermore, dormancy should be understood as a period of rest in the development and life cycle of a plant, which is characterized by the non-growth of the plant.

[0057] Furthermore, agricultural crops and cultivated plants should be understood to mean plants that are intentionally planted, cultivated or propagated by human intervention and are used in whole or in part as food, luxury food, therapeutics, as feed for animals or for technical purposes, for example as renewable raw materials.Furthermore, fruit trees or fruit plants should be understood to mean plants that form perennial flowers and trees.The term includes perennial trees or shrubs, which are perennial plants that are permanently maintained such that the axis becomes woody and the size of the shoot system above the ground increases year by year.

[0058] Such trees or shrubs which bear fruit are also defined as fruit trees and include 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 hybrid products or cultivars.

[0059] The formation of fruit flowers can occur differently in trees or shrubs, depending on the genus and species. In families of tropical plants such as the breadfruit (Artocarpus altitis), the jackfruit (Artocarpus heterophyllus), the papaya (Carica papaya) or the cocoa (Theobroma cacao), caulifolorie is the term used for the flowering of the stem, or in the following called cauliflorie, where individual flowers or inflorescences are formed on the woody stem.

[0060] However, depending on the genus and species, the formation of flowers in fruit trees can also take place via a subform of branch fruiting (Ramiflorie), where the formation of flowers occurs on the branches. Both forms of flowering can be found in cocoa. For this purpose, the formation of flowers in clusters occurs on 2-3 year old woody branches of secondary buds arranged in the axils of the leaves with meristems. According to the invention, agricultural crops and cultivated plants can in particular be treated. These agricultural crops and cultivated plants can be treated as naturally occurring plants, as hybrid products of these plants or as cultivars.

[0061] Thus, according to a further embodiment, the subject of the present invention is also the use of at least one compound from the group of the acylcyanamides of formula (I) or of formula (II) or their salts for regulating the reproductive growth of plants, in particular the reproductive growth of agricultural and cultivated plants, preferably the reproductive growth of fruit trees, or for breaking dormancy in fruit trees, where the plants, agricultural and cultivated plants or fruit trees are grapes (Vitis vinifera), kiwi (Actinidia deliciosa, Actinidia chinensis or Actinidia arguta), blueberries (Vaccinium myrtillus, Vaccinium corymbosum, Vaccinium virgatum, Vaccinium angustifolium or Vaccinium myrtilloides), cherries (Prunus avium or Prunus cerasus), plums or damsons (Prunus domestica), apples (Malus domestica or Malus orientalis), pears (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 hybrid products or cultivars thereof, are selected and treated.

[0062] According to a further embodiment, the present invention also provides a concentrate of a plant growth regulator. This concentrate serves to provide the acylcyanamide or its salt of the present invention as a plant growth regulator or dormancy stimulant in a user-friendly manner. Therefore, the present invention also provides a concentrate of a plant growth regulator for regulating the reproductive growth of plants, in particular the reproductive growth of agricultural crops and cultivated plants, preferably the reproductive growth of fruit trees, or for breaking the dormancy of fruit trees, which concentrate comprises: a) The following applies to formula (I) and formula (II):

[0063] [ka]

[0064] [ka]

[0065] In the formula, R 1 , R 2 , R 3 , R 4 , R 5 Group and cation M 1 , M 2 means, independently of each other: R 1 = Hydrogen, C1-C 20 Alkyl, C3-C 12 Cycloalkyl, C2-C 20 Alkenyl, C1-C 20 alkoxy, aryl, alkylaryl, arylalkyl or Q group, where Q is: Q=C1-C, each of which is substituted with a group of formula (III) or formula (IV). 20 Alkyl, C3-C 12 Cycloalkyl, C2-C 20 Alkenyl, C1-C 20 alkoxy, aryl, alkylaryl or arylalkyl;

[0066] [ka]

[0067] [ka]

[0068] M 1 , M 2 = Li, Na, K, 1 / 2Ca, 1 / 2Mg, or NR, independently of each other 2 R 3 R 4 R 5 and R 2 , R 3 , R 4 , R 5 = independently of each other hydrogen or C1-C 20 at least one active ingredient from the group of acylcyanamides of formula (I) or (II) or salts thereof, which is alkyl, b) For agricultural purposes Is it safe or Accept At least one additive from the group of approved solvents, oils, surfactants, or emulsifiers Including, The concentrate has an active ingredient concentration in the range of 100-600 g / l.

[0069] The active ingredient in the concentrate can be any of the acylcyanamides described herein, as well as any of the acylcyanamides described herein as preferred or alternatively preferred, and the concentrate has an active ingredient concentration in the range of 100-600 g / l. According to a preferred embodiment, the concentrate has an active ingredient concentration in the range of 200-600 g / l, in particular an active ingredient concentration in the range of 300-600 g / l.

[0070] According to a preferred embodiment, the concentrate is present as a solution, an emulsifiable solution or an emulsion, in particular as an aqueous solution or emulsion.

[0071] In this context and for the purposes of the present invention, the term emulsion is understood to mean a mixture of at least two liquid components that are not completely miscible with each other, in particular that have a miscibility gap. In this context, one component is dispersed as a dispersed or internal liquid phase in another coherent external liquid phase. For the purposes of the present invention, the term oil-in-water emulsion, also called O / W emulsion, means an emulsion in which an oil phase is dispersed in a coherent hydrophilic phase, preferably an aqueous phase. The oil phase comprises a hydrophobic, water-immiscible organic phase that contains oil. In this context, the oil phase is dispersed in the form of droplets in a hydrophilic phase, preferably an aqueous phase. The term water-in-oil emulsion, also called W / O emulsion, is understood to mean, in the sense of the present invention, an emulsion in which an aqueous phase (Wasserphase) or aqueous phase (waessrige phase) is dispersed in a coherent hydrophobic phase, preferably an oil phase. For the purposes of the present invention, the term emulsion also includes mini-emulsions and micro-emulsions.

[0072] Further, an emulsifiable solution should be understood to be one that either self-sustains as an emulsion after addition to water (or to the composition), or forms an emulsion upon mechanical mixing, such as stirring, after addition to water (or to the composition).

[0073] Thus, the present invention also provides a concentrate of a plant growth regulator for regulating the reproductive growth of plants, in particular the reproductive growth of agricultural crops and cultivated plants, preferably the reproductive growth of fruit trees, or for breaking dormancy in fruit trees, said concentrate comprising a solution, an emulsifiable solution or an emulsion, in particular an aqueous solution or emulsion, which comprises the following: a) The following applies to formula (I) and formula (II):

[0074] [ka]

[0075] [ka]

[0076] In the formula, R 1 , R 2 , R 3 , R 4 , R 5 Group and cation M 1 , M 2 means, independently of each other: R 1 = Hydrogen, C1-C 20 Alkyl, C3-C 12 Cycloalkyl, C2-C 20 Alkenyl, C1-C 20 alkoxy, aryl, alkylaryl, arylalkyl or Q group, where Q is: Q=C1-C, each of which is substituted with a group of formula (III) or formula (IV). 20 Alkyl, C3-C 12 Cycloalkyl, C2-C 20 Alkenyl, C1-C 20 alkoxy, aryl, alkylaryl or arylalkyl;

[0077] [ka]

[0078] [ka]

[0079] M 1 , M 2 = Li, Na, K, 1 / 2Ca, 1 / 2Mg, or NR, independently of each other 2 R 3 R 4 R 5 and R 2 , R 3 , R 4 , R 5 = independently of each other hydrogen or C1-C 20is alkyl, at least one active ingredient from the group of acylcyanamides of formula (I) or (II) or salts thereof, b) For agricultural purposes Is it safe or Accept At least one additive from the group of approved solvents, oils, surfactants, or emulsifiers Including, The solution, emulsifiable solution or emulsion has an active ingredient concentration in the range of 100 to 600 g / l.

[0080] Preferably the plant growth regulator concentrate, more preferably the plant growth regulator concentrate is or comprises a solution, emulsifiable solution, or emulsion, comprising: a) at least one active ingredient from the group of acylcyanamides of formula (I) or (II) or salts thereof, and b) For agricultural purposes Is it safe or Accept at least one additive from the group of solvents approved for use in c) For agricultural purposes Is it safe or Accept at least one additive from the group of oils, surfactants or emulsifiers approved for use in the manufacture of pharmaceuticals, and optionally d) at least one other formulation aid Including, The concentrate has an active ingredient concentration in the range of 100-600 g / l.

[0081] Further preferred are concentrates of plant growth regulators, which are in particular present as solutions, emulsifiable solutions or emulsions, in particular as aqueous solutions or emulsions, which in turn are a)R 1 , R 2 , R 3 , R 4 , R 5 Groups and cations M 1 , M 2 means, independently of each other: R 1 = Hydrogen, C1-C 20 Alkyl, C3-C 12Cycloalkyl, C2-C 20 Alkenyl, C1-C 20 an alkoxy or Q group, where Q is: Q=C1-C, each of which is substituted with a group of formula (III) or formula (IV). 20 Alkyl, C3-C 12 Cycloalkyl, C2-C 20 Alkenyl, C1-C 20 is an alkoxy; M 1 , M 2 = Li, Na, K, 1 / 2Ca, 1 / 2Mg, or NR, independently of each other 2 R 3 R 4 R 5 and R 2 , R 3 , R 4 , R 5 = independently of each other hydrogen or C1-C 20 is alkyl, It contains at least one active ingredient from the group of acylcyanamides of formula (I) or (II) or their salts.

[0082] Particularly preferred are concentrates of the plant growth regulators in the form of solutions, emulsifiable solutions or emulsions, in particular as aqueous solutions or emulsions, which in turn are a) at least one active ingredient from the group consisting of sodium formyl cyanamide, sodium acetyl cyanamide, sodium propionyl cyanamide, sodium n-butyryl cyanamide, sodium isobutyryl cyanamide, sodium methoxycarbonyl cyanamide, sodium ethoxycarbonyl cyanamide, potassium formyl cyanamide, potassium acetyl cyanamide, potassium propionyl cyanamide, potassium n-butyryl cyanamide, potassium isobutyryl cyanamide, potassium methoxycarbonyl cyanamide or potassium ethoxycarbonyl cyanamide, b) For agricultural purposes Is it safe or Accept at least one additive from the group of solvents approved for use in c) For agricultural purposes Is it safe or Accept At least one additive from the approved group of oils, surfactants or emulsifiers Including, The concentrate has an active ingredient concentration in the range of 100-600 g / l.

[0083] According to the present invention, the plant growth concentrate can contain a solvent. In the context of the present invention, a solvent is to be understood as any solvent suitable for use in agriculture. A suitable solvent is therefore a solvent that is compatible with plants. Water or organic solvents, in particular water-miscible organic solvents, are particularly preferred.

[0084] In the context of the present invention, a water-miscible organic solvent is to be understood as any organic solvent which by definition differs from water and which in a 1:1 mass ratio with water at 20° C. results in a single-phase system.

[0085] The research underlying the present invention has shown that an organic solvent selected from the group consisting of water-soluble alcohols, ketones, nitriles, amides, glycols, polyglycols and mixtures thereof may be used as the water-miscible organic solvent.

[0086] Thus, preferred solvents are water and organic solvents selected from the group consisting of ethanol, isopropanol, n-propanol, glycols, glycerol, polyglycols, acetone, methyl ethyl ketone, acetonitrile, propionitrile, formamide, dimethylformamide, N-Methylpyrrilidon, and mixtures thereof.

[0087] According to a particularly preferred embodiment of the invention, the concentrate comprises as solvent water, ethanol, isopropanol, n-propanol, glycol, glycerol, polyglycol or mixtures thereof. Concentrates comprising these solvents have been shown to be particularly storage-stable liquid formulations that can be stored for long periods of time.

[0088] A subject of the present invention is therefore also a concentrate of a plant growth regulator which is a solution, an emulsifiable solution or an emulsion comprising as solvent a solvent selected from the group consisting of water, ethanol, isopropanol, glycol, polyglycol, glycerol or a mixture of these solvents.

[0089] According to an alternative formulation, the concentrate can also be prepared as an emulsifiable solution.According to a further development of the present invention, the concentrate that is prepared as an emulsifiable solution and contains less than 10% by weight, in particular less than 5% by weight, more preferably less than 3% by weight of water, even more preferably less than 2% by weight of water, very particularly preferably less than 1% by weight of water, is also the subject of the present invention.

[0090] According to the present invention, the plant growth concentrate may contain oil. Here, in the context of the present invention, oil should be understood as any oil suitable for use in agriculture. A suitable oil is therefore an oil that is compatible with plants. In particular, the oil may be selected from the group of natural oils, especially oils of animal or vegetable origin, and synthetic oils. According to the present invention, natural oils, especially vegetable oils, may be used as oils. Vegetable oils are generally known and commercially available. The term vegetable oil in the sense of the present invention is understood to mean oils from plant species that produce oils such as soybean oil, corn oil, sunflower oil, rapeseed oil, cottonseed oil, linseed oil, coconut oil, palm oil, safflower oil, peanut oil, walnut oil, olive oil or Rhizinusoel, especially rapeseed oil, and vegetable oil is also understood to mean their transesterification products, for example alkyl esters such as rapeseed oil methyl ester or rapeseed oil ethyl ester.

[0091] The vegetable oil according to the invention preferably has a C 10 ~C 24 It is a mixture of fatty acid esters. 10 ~C 24 Fatty acid esters can be, for example, unsaturated or saturated C 10 ~C 24Esters of fatty acids, especially those having an even number of carbon atoms, more preferably 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-ensaeure), petroselinic acid (octadecyl-6-ensaeure), oleic acid (Octadecyl-9-ensaeure), Elaidic acid (Octadecyl-9-ensaeure), Gadoleic acid (Eicosane-9-enoic acid), Erucic acid (13-docosenoic acid), Linoleic acid (Octadeca-9,12-dienoic acid), α-Linolenic acid (Octadeca-9,12,15-trienoic acid), γ-Linolenic acid (Octadeca-6,9,12-trienoic acid), or mixtures thereof.

[0092] Examples of vegetable oils are glycerol or glycol and C 10 ~C 24 C with fatty acids 10 ~C 24 Fatty acid esters (especially of the acids listed), or e.g. C 10 ~C 24 The glycerol or glycol ester of fatty acid is mixed with a C1-C ethanol such as methanol, ethanol, propanol or butanol. 20 C, such as can be obtained by transesterification with alcohols 10 ~C 24 These are fatty acid esters (specifically esters of the acids listed).

[0093] The vegetable oil may be present in the liquid composition according to the invention, for example in the form of commercially available vegetable oils, in particular rapeseed oils such as rapeseed oil methyl ester, e.g. Phytorob™ B (Novance, France), Edenor™ MESU and Agnique™ ME series (Cognis, Germany), Radia™ (ICI) or Prilube™ (Petrofina).

[0094] To the extent that synthetic oils are used, they include mineral oils, kerosene, white oils and synthetic fatty acid esters, especially C 11 ~C 19 Preferred are esters of fatty acids having an odd number of carbon atoms, such as fatty acids (especially those selected from the group consisting of undecanoic acid, tridecanoic acid, pentadecanoic acid, margaric acid (heptadecanoic acid) and nonadecanoic acid) with mono-, di- or trihydric C1-C5 alcohols (especially methanol, ethanol, propanol or butanol).

[0095] Thus, according to the invention, the oil used may in particular be an oil selected from the group consisting of mineral oil, kerosene, white oil, saturated linear or branched aliphatic hydrocarbons, esters of saturated or unsaturated fatty acids with mono-, di- or trihydric C1-C5 alcohols, ethers of fatty alcohols with C1-C5 alcohols, and mixtures thereof.

[0096] Preferably, mineral oils, mineral oils with reduced aromatic content, mineral oils containing no aromatics, fatty oils, i.e. glycerol esters of fatty acids having 4 to 24 C atoms, C1 to C 20 Oils from the group consisting of esters of alcohols and fatty acids having 4 to 24 C atoms, preferably the methyl or ethyl esters of fatty acids having 4 to 24 C atoms, can also be used according to the invention.

[0097] Particularly suitable are C1-C 20 They are oils from the group comprising esters of alcohols with fatty acids having 4 to 24 C atoms, in particular the methyl or ethyl esters of fatty acids having 4 to 24 C atoms.

[0098] The subject of the invention therefore also relates to, as oil, an oil from the group of vegetable oils, in particular C 10 ~C 24 Vegetable oils from the group of fatty acid esters, especially C 10 ~C 24A concentrate of a plant growth regulator which is a solution, emulsifiable solution or emulsion comprising a methyl, ethyl, glyceryl or glycol ester of a fatty acid, particularly rapeseed methyl ester.

[0099] According to the invention, the concentrate of the plant growth regulator may in particular comprise 0.1 to 20% by weight of at least one oil (especially a vegetable oil), but preferably also 0.1 to 15% by weight of at least one oil (especially a vegetable oil), more preferably 0.1 to 12% by weight of at least an oil (especially a vegetable oil), particularly preferably 0.1 to 10% by weight of at least an oil.

[0100] In particular, surfactants having an HLB value of 5 to 20 may be used. Furthermore, in particular cationic surfactants, anionic surfactants or nonionic surfactants may also be used as surfactants. Particularly preferably, nonionic surfactants may be used.

[0101] A subject of the present invention is therefore also a concentrate of a plant growth regulator which is a solution, an emulsifiable solution or an emulsion comprising as surfactant a surfactant selected from the group consisting of nonionic surfactants.

[0102] The following applies to formulae (VII) and (VIII):

[0103] [ka]

[0104] [ka]

[0105] In the formula, R 11 , R 12 The radicals and the subscripts n, m may simultaneously or independently mean: 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 between 2 and 20, m = a number from 1 to 5 Further preferred non-ionic surfactants can be used which contain one or more compounds from the group of ethoxylates of formula (VII), fatty alcohol glucosides of formula (VIII), or mixtures thereof.

[0106] In the context of the present invention, mono- or polyfunctional siloxane groups are in particular a) one or more chlorosilanes selected from the group consisting of trimethylchlorosilane, dimethyldichlorosilane, and methyltrichlorosilane; and b) one or more 3-heteropropyl-substituted chlorosilanes selected from the group consisting of 3-heteropropyl-trichlorosilane, 3-heteropropyl-methyldichlorosilane, and 3-heteropropyl-dimethylchlorosilane, where 3-heteropropyl is 3-chloropropyl, 3-hydroxypropyl, or 3-(hydroxyethoxy)propyl. By this is meant the siloxane groups formed by mixed hydrolysis of

[0107] Typical mono- or polyfunctional siloxane groups which can be prepared from these building blocks are given by the following formulae, where formula (IX) represents a monofunctional siloxane group, formula (X) represents a difunctional siloxane group, and formulas (XI) and (XII) represent v-functional siloxane groups, with the following applying to formulae (IX), (X), (XI) and (XII):

[0108] [ka]

[0109] where the subscript x is as follows: x = a number between 0 and 15, especially a number between 0 and 10, especially a number between 3 and 10,

[0110] [ka]

[0111] where the subscripts y and z are as follows: y = a number between 2 and 20, especially a number between 2 and 10, and especially a number between 3 and 10, z = a number between 0 and 10, especially a number between 0 and 5, and especially a number between 1 and 3,

[0112] [ka]

[0113] where the subscripts y, u and v are as follows: y = a number between 2 and 20, especially a number between 2 and 10, and especially a number between 3 and 10, u = a number between 0 and 15, especially a number between 0 and 10, especially a number between 0 and 3, v = a number from 0 to 4, especially a number from 0 to 3.

[0114] Particularly preferred are v-functional siloxane groups, in particular siloxane groups of formula (XII), which is a special case of formula (XI) where u=v=0, and the following applies to formula (XII):

[0115] [ka]

[0116] According to a particularly preferred embodiment, R 11 The groups and subscript n are as follows: R 11 = a linear or branched alkyl group having 8 to 18 carbon atoms, or an alkyl-substituted phenyl group, or a monofunctional siloxane of formula (VII) where x=a number from 3 to 10, or a difunctional siloxane of formula (VIII) where z=a number from 1 to 3 and y=a number from 2 to 10, or a polyfunctional siloxane group of formula (X) where u=a number from 0 to 3, 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 between 2 and 20, especially a number between 2 and 10, especially a number between 3 and 10 There is provided the use of an ethoxylate of formula (VII) as a non-ionic surfactant.

[0117] According to a further preferred embodiment, mixtures of different ethoxylates of formula (VII) may also be used as non-ionic surfactants. In this case, 11 Applies to the group and subscript n: R 11 = a polyfunctional siloxane group of formula (XI), where u = a number from 0 to 3, v = a number from 0 to 3, and y = a number from 2 to 10; n = a number between 2 and 20, especially a number between 2 and 10, especially a number between 3 and 10 Mixtures of at least two different ethoxylates of formula (VII) have been shown to be particularly effective.

[0118] According to a further preferred embodiment, mixtures of different ethoxylates of formula (VII) may also be used as non-ionic surfactants. In this case, 11 Applies to the group and subscript n: R 11 = n-dodecyl, n-hexadecyl and n-octadecyl, n = a number between 2 and 20, especially a number between 2 and 10 Mixtures of at least two different ethoxylates of formula (VII) have been shown to be particularly effective.

[0119] Particularly preferred are the following: 1 Applies to the group and subscript n: R 11= n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, methyldecyl, methyldodecyl, methyltetradecyl or a siloxane of formula (XII), n = 4 to 8, It is an ethoxylate of formula (VII).

[0120] According to an alternative preferred embodiment, the following is 12 Applied to the group and subscript m: R 12 = a linear alkyl group having 8 to 18 carbon atoms, m = a number between 2 and 5, There is provided the use of fatty alcohol glucosides of formula (VIII) as non-ionic surfactants.

[0121] It is very particularly preferred that 12 Applied to the group and subscript m: R 12 = n-hexadecyl or n-octadecyl, m is a number between 3 and 5. It is a fatty alcohol glucoside of formula (VIII).

[0122] According to the invention, the concentrate of the plant growth regulator may in particular comprise 0.1 to 10% by weight of at least one surfactant, in particular a non-ionic surfactant. However, particularly preferably, the composition may also comprise 0.1 to 5% by weight of at least one surfactant, in particular a non-ionic surfactant, very particularly preferably 0.1 to 3% by weight of at least one surfactant, in particular a non-ionic surfactant.

[0123] The concentrate of the plant growth regulator according to the present invention may contain at least one emulsifier as a safe or approved additive.Preferably, the concentrate according to the present invention contains 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.

[0124] According to a particularly preferred embodiment, the composition comprises at least one oil-in-water emulsifier and / or non-ionic emulsifier, very particularly preferably at least one non-ionic emulsifier from the class of oil-in-water emulsifiers.

[0125] Thus, a concentrate of the plant growth regulator which is a solution, an emulsifiable solution, or an emulsion, containing as an emulsifier an emulsifier selected from the group consisting of non-ionic oil-in-water emulsifiers, is also a subject of the present invention.

[0126] Preferred nonionic emulsifiers are selected from the group comprising 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.

[0127] Preferred cationic emulsifiers are selected from the group comprising long chain quaternary ammonium compounds such as alkyltrimethylammonium salts and dialkyldimethylammonium salts, having C8 to C22 alkyl groups.

[0128] Preferred anionic emulsifiers are selected from the group comprising fatty alcohol sulfates, alkyl ether sulfates and alkyl benzene sulfonates.

[0129] Preferred amphoteric emulsifiers are selected from the group comprising betaines such as fatty acid amidoalkyl betaines and sulfobetaines and C8-C22 alkyl betaines.

[0130] Particularly preferred are non-ionic emulsifiers from the class of ethoxylated fatty alcohols, in particular ethoxylated C8-C20 alkyl alcohols. Also preferred are non-ionic O / W emulsifiers from the class of ethoxylated C8-C20 alkyl alcohols, very particularly preferably iso-C13 ethoxylates.

[0131] According to the invention, the concentrate of the plant growth regulator may in particular comprise 0.1 to 10% by weight of at least one emulsifier, but particularly preferably the composition may also comprise 0.1 to 5% by weight of at least one emulsifier, very particularly preferably 0.1 to 3% by weight of at least one emulsifier.

[0132] Within the scope of the present invention, it may further be provided that the concentrate of the plant growth regulator comprises or contains further ingredients, namely formulation auxiliaries.

[0133] Preferably, the concentrate further comprises or contains at least one formulation auxiliary selected from the group consisting of pH adjusters, colorants, thickeners, dispersants, solubilizers, viscosity modifiers, labelling agents and bittering agents, in particular those approved for agricultural purposes.

[0134] These formulation auxiliaries can be included or contained in the solution in an amount of up to 5% by weight. In addition to the additives from the group of solvents, oils, surfactants and emulsifiers described herein, these formulation auxiliaries can be used, and these formulation auxiliaries do not affect the plant physiological effect of the spray mixture produced from the concentrate according to the present invention. Thus, these additional formulation auxiliaries solely meet the application-specific requirements.

[0135] It is particularly preferred that the formulation auxiliaries are included or contained in an amount of up to 4% by weight, more preferably up to 3% by weight, particularly preferably up to 2% by weight. If the concentrate according to the invention contains formulation auxiliaries due to application-specific requirements, the concentrate may preferably contain or contain at least 0.01% by weight, in particular at least 0.1% by weight (in each case based on the total weight of the concentrate) of formulation auxiliaries.

[0136] According to the invention, the plant growth concentrate has an active ingredient concentration in the range of 100-600 g / l. Preferably, the concentrate according to the invention comprises or contains at least 10% by weight and at most 60% by weight (based on the total weight of the concentrate) of at least one compound from the group of acylcyanamides of formula (I) or formula (II) or their salts. Even more preferably, the concentrate according to the invention comprises or contains at least 20% by weight, even more preferably at least 30% by weight, very particularly preferably at least 35% by weight (based on the total weight of the concentrate) of at least one compound from the group of acylcyanamides of formula (I) or formula (II) or their salts.

[0137] Therefore, a) 10 to 60% by weight of at least one active ingredient selected from the group consisting of acylcyanamides of formula (I) or (II) or salts thereof, 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, surfactant and / or emulsifier, and optionally d) 0.01 to 5% by weight of at least one further formulation auxiliary, Including, the proportions of a) to d) total 100% by weight, in particular at least one compound from the group of acylcyanamides or their salts being present in the concentrate in dissolved form; Concentrates of plant growth regulators, in particular those in the form of a solution, an emulsifiable solution or an emulsion, are also the subject of the present invention.

[0138] Very particularly preferably, the concentrate of the plant growth regulator according to the invention is a) 30 to 60% by weight of at least one active ingredient selected from the group consisting of acylcyanamides of formula (I) or (II) or salts thereof; 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, emulsifier or surfactant, and optionally d) 0.01 to 3% by weight of at least one other formulation auxiliary; Including, The proportions of a) to d) add up to 100% by weight, in particular at least one compound from the group of the acylcyanamides or their salts being present in dissolved form in the concentrate.

[0139] However, it can also be provided that the concentrate of the plant growth regulator according to the invention does not have further components besides said components a), b), c) and optionally d) and thus consists of said components.

[0140] In a further advantageous embodiment of the invention, it can be provided that 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., simultaneously or independently of this, the concentrate has a surface tension of at least 5 mN / m at a temperature of 25° C.

[0141] 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, even more preferably less than 50 mPa·s at 25° C.

[0142] The concentrates of the plant growth regulator according to the present invention can provide high concentrations of active ingredients. However, for the application of the active ingredients described herein, these concentrations are too high. These concentrates must be diluted before their application, especially as a spray, dip or brush solution.

[0143] Application tests have shown that the active ingredients described herein from the group of acylcyanamides of formula (I) or formula (II) or their salts can be used, in particular as spray, immersion or brush solutions, preferably in concentrations ranging from 0.05 to 1 mol / l.

[0144] More preferably, it has been shown that these active ingredients can be used in concentrations ranging from 0.05 to 0.8 mol / l, in particular from 0.05 to 0.6 mol / l, particularly preferably from 0.05 to 0.5 mol / l, in particular as a spray, immersion or brush solution.

[0145] More preferably, it has been shown that these active ingredients can be used in concentrations ranging from 0.1 to 1 mol, in particular from 0.1 to 0.8 mol / l, in particular from 0.1 to 0.6 mol / l, particularly preferably from 0.1 to 0.5 mol / l, in particular as a spray, immersion or brush solution.

[0146] Furthermore, the use of concentrates of the plant growth regulators described herein, or spray or dipping solutions prepared from or with said concentrates, for regulating the reproductive growth of plants, in particular the reproductive growth of agricultural crops and cultivated plants, preferably the reproductive growth of fruit trees, or for breaking dormancy in fruit trees, is encompassed by the present invention.

[0147] Thus, according to a further embodiment, spray solutions of plant growth regulators, including solutions or emulsions, for regulating the reproductive growth of plants, in particular the reproductive growth of agricultural crops and cultivated plants, preferably the reproductive growth of fruit trees, or for breaking dormancy in fruit trees, are also the subject of the present invention, which are a) The following applies to formula (I) and formula (II):

[0148] [ka]

[0149] [ka]

[0150] In the formula, R 1 , R 2 , R 3 , R 4 , R 5 Group and cation M 1 , M 2means, independently of each other: R 1 = Hydrogen, C1-C 20 Alkyl, C3-C 12 Cycloalkyl, C2-C 20 Alkenyl, C1-C 20 an alkoxy, aryl, alkylaryl or arylalkyl, or Q group, where Q is: Q=C1-C, each of which is substituted with a group of formula (III) or formula (IV). 20 Alkyl, C3-C 12 Cycloalkyl, C2-C 20 Alkenyl, C1-C 20 alkoxy, aryl, alkylaryl or arylalkyl;

[0151] [ka]

[0152] [ka]

[0153] M 1 , M 2 = Li, Na, K, 1 / 2Ca, 1 / 2Mg, or NR, independently of each other 2 R 3 R 4 R 5 and R 2 , R 3 , R 4 , R 5 = independently of each other hydrogen or C1-C 20 at least one active ingredient from the group of acylcyanamides of formula (I) or (II) or salts thereof, which is alkyl, b) For agricultural purposes Is it safe or Accept At least one additive or auxiliary from the group of approved solvents, oils, surfactants or emulsifiers Including, The aqueous solution has an active ingredient concentration in the range of 0.05 to 1 mol / l, particularly 0.05 to 0.8 mol / l, particularly 0.05 to 0.6 mol / l, and especially 0.05 to 0.5 mol / l.

[0154] Thus, according to a further embodiment, a method for regulating the reproductive growth of plants, in particular the reproductive growth of agricultural crops and cultivated plants, preferably the reproductive growth of fruit trees or breaking the dormancy of fruit trees, comprising the application by immersion, brushing or spraying of the branches, shoots or buds of plants, agricultural crops and cultivated plants or fruit trees during their dormancy, with an aqueous solution comprising at least one active ingredient from the group of acylcyanamides of formula (I) or formula (II) or their salts, is also the subject of the present invention.

[0155] The following examples further illustrate the principles of the present invention. EXAMPLES

[0156] Working Example Synthesis Example Example A-1 Synthesis of sodium acetylcyanamide (CAS 84946-07-6) from solid cyanamide 180.1 g (1.0 mol) of a 30% solution of sodium methylate were introduced. Under good cooling, a total of 42.25 g (1.005 mol) of solid cyanamide were introduced in portions at max. 25° C. 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., fraction 1 of precipitated sodium acetylcyanamide was filtered off and dried at 60° C. The mother liquor obtained was evaporated to half its volume, cooled to 10° C. and fraction 2 of precipitated sodium acetylcyanamide was filtered off and dried. In total, the following was obtained: Fraction 1: 75g (71% yield) with 99.4% content, melting point 239°C Fraction 2: 19 g (18% yield) at 99.0% content, melting point 238°C 1 H-NMR in DMSO 1.70 ppm (s), 13C-NMR 180.75, 122.60, 25.26 ppm

[0157] Example A-1a Synthesis of sodium acetylcyanamide (CAS 84946-07-6) from sodium hydrogen cyanamide 120 g of methanol and 88.8 g (1.20 mol) of methyl acetate were introduced. 64.04 g (1.0 mol) of sodium hydrogen cyanamide were suspended therein. The reaction mixture was heated at 70° C. for 10 hours. It was then completely evaporated to dryness and the solid obtained was after-dried in vacuum at 60° C. (nachgetrocknet). 106 g (100% yield) of sodium acetylcyanamide with a content of 98.9% were obtained.

[0158] Example A-1b Synthesis of acetylcyanamide (CAS 5634-51-5) as the free NH acid 120 g of methanol and 88.8 g (1.20 mol) of methyl acetate were introduced. 64.04 g (1.0 mol) of sodium hydrogen cyanamide were suspended therein. The reaction mixture was heated at 70 °C for 10 hours. It was then cooled and another 500 g of methanol were added. At 10-20 °C, 49.0 g (0.5 mol) of concentrated sulfuric acid were added to precipitate sodium sulfate. The suspension was filtered, rewashed with methanol and the combined filtrates were evaporated almost completely. Density 1.100 g / cm, each measured at 20 °C. 3 and the refractive index n D 84 g of oil was obtained having an affinity for 1.425. The yield was quantitative.

[0159] Example A-1c Synthesis of potassium acetylcyanamide (CAS 1146597-19-4) 280.4 g (1.0 mol) of a 25% solution of potassium methylate were introduced. With good cooling, a total of 42.25 g (1.005 mol) of solid cyanamide were introduced in portions at max. 25° C. 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 about half the volume and cooled to 10° C. The precipitated solid was filtered off and dried at 60° C. 94 g of a white solid were obtained with a N content of 23.0%. The yield was 77%.

[0160] Example A-2 Synthesis of sodium formylcyanamide (CAS 71675-63-3) 909.5 g (5.0 mol) of a 29.7% sodium methylate solution were introduced. Under good cooling at 10-20°C, a total of 211.05 g (5.0 mol) of 99.6% solid cyanamide were introduced in portions. Then, 250 ml of methanol were added to ensure good stirring capacity. Then, 309.55 g (5.0 mol) of 97.0% formic acid methyl ester were added under cooling. The reaction mixture was heated to about 38°C (strong reflux) for a total of 18 hours. Then, it was 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 after-dried (nachgetrocknet) (fraction 2). In total, the following was 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

[0161] Examples A-3 to A-15 Further synthesis of sodium acylcyanamide Further syntheses were carried out analogously to Example A-1a from sodium hydrogen cyanamide. Depending on the target compound desired in each case, 1.2 mol of the carboxylic acid methyl ester was introduced into 120 of methanol, 64.04 g (1.0 mol) of sodium hydrogen cyanamide was suspended therein, and the reaction mixture was heated to reflux (about 65° C.) for almost 10 hours. The reaction mixture obtained was partially evaporated, mixed with 100 g of tert-butyl methyl ether, and the suspension obtained was filtered off at 10° C. The respective products were washed with tert-butyl methyl ether and dried at 60° C.

[0162] Tables 1 and 2 below summarize the respective materials, deviations from the above standard specifications (if applicable), yields and properties of the products obtained.

[0163] [Table 1-1]

[0164] [Table 1-2]

[0165] [Table 2]

[0166] Example of concentrate production Example B-1 Sodium acetylcyanamide as an aqueous solution containing surfactants 250 g of sodium acetylcyanamide from Example A-1 was dissolved in 600 g of water, to which 2.4 g of nonionic surfactant BreakThru™ OE-446 (manufacturer Evonik) was added, and the mixture was made up to a total of 1000 g with water. A clear solution was obtained.

[0167] Example B-1a Sodium acetylcyanamide as an emulsifiable solution in ethanol / water / biodiesel / surfactant 200g of sodium acetylcyanamide from Example A-1 was dissolved in 600g of a mixture of 80% by weight ethanol and 20% by weight water. 50g of rapeseed oil methyl ester, 2.4g of nonionic surfactant BreakThru™ S-240 (manufacturer Evonik), 20mg of dye Iron Blue ABL9-L (manufacturer BASF) were added. The mixture was filled up to 1000g with ethanol / water. A slightly blue transparent solution was obtained, which was easily emulsifiable in water.

[0168] Example B-1b Potassium acetylcyanamide as a solid 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 to give a white solid that readily dissolved in water and foamed slightly.

[0169] Example B-2 Sodium formylcyanamide as an aqueous solution containing surfactants 250 g of sodium formylcyanamide from Example A-2 was dissolved in 500 g of water, to which was added 2.4 g of the nonionic surfactant BreakThru™ OE-446 and 20 mg of the dye Iron Blue ABL9-L, and made up to 1000 g with water. A clear, blue concentrated solution was obtained.

[0170] Example B-3 Sodium propionyl cyanamide as an aqueous solution containing surfactants 250 g of sodium propionylcyanamide from Example A-2 was dissolved in 500 g of water, to which was added 2.4 g of the nonionic surfactant BreakThru™ OE-446 and 20 mg of the dye Iron Blue ABL9-L, and made up to 1000 g with water. A clear, blue concentrated solution was obtained.

[0171] Reference example B-16 Preparation of Cyanamide-Containing Concentrates 400 g of pure cyanamide was dissolved in 600 g of water. The pH value was adjusted to 4.2 with about 0.1 g of phosphoric acid. 10 g of BreakThru™ OE446 and 20 mg of Iron Blue ABL9-L were added. A blue concentrated solution B-16 was obtained.

[0172] Storage stability of concentrated solutions B-1, B-2, and B-3 compared to B-16 (reference) The concentrated solutions from B-1, B-2, B-3 and the cyanamide-containing reference solution B-16 were set at 60° C. and samples were taken in each case after different periods of time. These were immediately analyzed by ion chromatography for the acylcyanamide and cyanamide content, respectively. The respective starting solutions stored at −18° C. served as references. In each case the content was taken as 100% and the decrease in concentration was determined in relation to this.

[0173] [Table 3]

[0174] The results show that the solutions of sodium acetylcyanamide (B-1) and sodium propionylcyanamide (B-3) have a much better shelf life and therefore better storability than the corresponding concentrated solutions of cyanamide (B-16) of the prior art, which is a decisive advantage for agricultural handling.

[0175] Greenhouse test example Greenhouse trials were conducted using cut fruit tree branches placed in water jars and maintained under controlled conditions of approximately 22°C temperature and natural light. Branches from the following fruit tree species were used:

[0176] C1: Tafelapfel, Boikenapfel type Table apple: Malus domestica type Boiken, first described in 1828 in Bremen after Deichvogt Boiken. Apple type for rough sites, and scattered fruit type suitable for almost all soils. It requires heavy soils and a not too warm location. Tree growth is strong at first, later medium. The old crown becomes broadly globular and loosely branched. Flowering starts from mid-late, lasts long, petals are large, almost pink. Harvest starts late (October) and is irregular; it has a long storage life and pressure resistance. The type respires less during storage and the quality improves as it matures.

[0177] C2: Edible apple, Zabergaeu-Renette type Table apple: Malus domestica type Zabergeu-Renettte was first developed in 1885 in Hausen ad Zaber / Baden-Wuerttemberg as an adventitious seedling and initially grown as "Hausener Graue Renettte". No defined storage type; heavy soils (loam) are required. Tree growth is initially strong with oblique upright leading branches, later medium with flattened branches. Crown is broad, flattened globular, with a flattened fruiting wood. Leaves are large, broadly elliptical, with clearly divided tips. Triploid type with late and long-lasting flowering. Harvest starts early, high in the middle, slightly alternate.

[0178] C3: Edible cherries (Tafelkirsche), Burlat type Edible cherries: Prunus avium type Bigarreau Burlat or Hativ Burlat is a strong-growing, rather sparsely growing, sweet cherry tree with lateral shoots. The type has been known since 1930 and is one of the most important types in commercial cultivation. Flowering is early, followed by an early ripening week (end of May, Ende Mai 2. Kirschsorte), and the harvest starts late. The moderate but regular harvest identifies the type as a secondary species for early and dry areas.

[0179] C4: Grape, Pinot Noir type Grapes: Vitis vinifera subsp. vinifera type Pinot Noir is an important high quality red wine type that has been around for perhaps 2000 years. It is grown worldwide because it produces high quality red wine and has sufficient winter frost resistance. It requires early and good areas with deep, warm, medium weight and fertile soils with a good water supply. Pinot Noir produces regular, medium to high yields. However, there are many clones that differ in yield, berry size and looseness.

[0180] Branches or shoots were pruned in November, approximately one week after the last leaf had fallen and before the first night frost. Branch cuttings were cut to equal lengths and divided into groups of five branches each to achieve a uniform number of buds and shoot formation per group.

[0181] The test solutions were prepared directly, i.e. without intermediate preparation of concentrates. 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 filled to a total of 500 g with water. Of the biscyanamides A-14 and A-15, 0.075 mol each was filled to 500 g in a similar manner. These test solutions (combinations with the four species / types Cx above) were given test numbers Cx-A1 to Cx-A15.

[0182] The negative and positive control reference solutions, respectively, were as follows: Cx-0: 500g of pure water (negative control) Cx-0a: 0.15 g BreakThru™ OE-446 (negative control) filled to 500 g with purified water Cx-16: 0.15 mol (6.30 g) pure cyanamide and 0.15 g BreakThru™ OE-446 (positive control), made up to 500 g with water.

[0183] The test solutions (15 test solutions) were each placed in a photo dish and five of each branch were dipped into the solution, further moistening with a brush if necessary until the entire surface was moistened. The branches were placed on filter paper to allow excess liquid to drip off and allowed to dry for 20 minutes. Five branches of each uniform treatment were then placed in a jar of pure water and set up in the greenhouse as described above.

[0184] After the specified evaluation times T1-T6 (determined after 14, 16, 21, 27, 36, and 56 days, respectively, after the application of the test solution "day 0"), the bud development of each test group was evaluated using the following rating scale: Stage 0: No change in the buds. Stage 1: The buds are swelling slightly and the first green tips are visible. Stage 2: Strong, swollen green buds. Stage 3: Unopened buds, leaves or flower roots are already visible. Stage 4: The flower bud is fully developed but still closed, with the white petals already visible. In the case of the vine, stage 4 was the unfolding of the first leaves. Stage 5: Full flower opening or, in the case of vines, development of the flower roots on a fully leafed bud ("Gescheine").

[0185] Exam evaluation An effect of breaking dormancy is present if, depending on the species (fruit tree) under investigation, evaluation stage 4 is reached or exceeded after n days (depending on the species (fruit tree)) compared to the negative control (water or water with surfactant). The greater the difference in time and / or evaluation stage compared to the negative control, the better the effect of breaking dormancy is classified as. n (for C1, C2, C4): 36 days n (for C3): 27 days

[0186] A good dormancy-breaking effect is present if, depending on the species (fruit tree) under investigation, evaluation stage 4 is reached or exceeded after n days (depending on the species (fruit tree)) compared to the negative control (water or water with surfactant). The greater the difference in time and / or evaluation stage compared to the negative control, the better the dormancy-breaking effect is classified as. n (for C1, C2, C4): 27 days n (for C3): 21 days

[0187] [Table 4]

[0188] The test results show that 12 of the investigated substances (80%) have an effect on breaking dormancy according to the above definition (see A1, A2, A3, A5, A6, A7, A8, A10, A11, A12, A13, A14), while 6 of the investigated substances (40%) show a good to very good dormancy breaking effect on the investigated species (see A2, A5, A6, A7, A8, A10).

[0189] [Table 5]

[0190] The test results show that 9 of the investigated substances (60%) have an effect on breaking dormancy according to the above definition (see A1, A2, A3, A6, A7, A9, A11, A12, A15). 2 of the investigated substances (13%) show a good to very good dormancy breaking effect on the investigated species (see A9, A15).

[0191] Overall results for apples (C1, C2) Depending on the type of apple tested, 14 of the 15 tested substances showed an effect in breaking dormancy in at least one apple type. Particularly highlighted are substances A6, A7, A9 and A15, which showed a similar or equally good effect compared to the positive control.

[0192] [Table 6]

[0193] The test results show that 9 of the investigated substances (60%) have a dormancy-breaking effect according to the above definition (see A1, A2, A4, A5, A6, A10, A11, A12, A14). 7 of the investigated substances (47%) even show a good to very good dormancy-breaking effect on the investigated species of cherries (see A1, A2, A4, A5, A10, A11, A14). In contrast to apple seeds (C1, C2), substance A4 has a good dormancy-breaking effect on cherry seeds. In this regard, it should also be emphasized that substance A11 shows an effect comparable to that of cyanamide.

[0194] [Table 7]

[0195] The test results show that eleven of the investigated substances (73%) have a dormancy-breaking effect according to the above definition (see A1, A2, A3, A4, A7, A8, A9, A11, A12, A14, A15). One of the investigated substances (7%) even shows a good to very good dormancy-breaking effect on the investigated varieties of wine (see A2). In this regard, it should be emphasized that substance A2 shows an effect equivalent to that of cyanamide.

[0196] Overall Results The compilation of results for four fruit species C1-C4 shows that the sodium acylcyanamides A1-A15 according to the invention all exert a more or less strong effect in breaking dormancy compared to the water reference (negative control), the effect being similar but in some cases somewhat weaker or slightly delayed compared to the positive reference cyanamide (=standard agent according to the prior art), the efficiency of which is achieved in some cases depending on the species.

[0197] Example of Preparing a Spray Mixture from a Concentrate Example D-1 Preparation of sodium acetylcyanamide-containing spray mixture 10 parts of the concentrated solution from Example B-1 were diluted with 90 parts of water. A clear aqueous solution was obtained, which was used as a spray mixture. The spray mixture contained about 0.24 mol of active ingredient acetylcyanamide per liter.

[0198] Example D-1a Preparation of sodium acetylcyanamide-containing spray mixture-emulsion 8 parts of the concentrated solution from Example B-1a was added to 92 parts of water. The two components mixed to form a bluish, slightly cloudy emulsion. The spray mixture contained approximately 0.15 moles of acetylcyanamide per liter.

[0199] Reference example D-18 Preparation of Cyanamide-Containing Spray Mixtures 2.5 parts of the concentrated solution from Example B-18 was mixed with 97.5 parts of water to obtain Reference Spray Mixture D-18. The spray mixture contained approximately 0.24 moles of active ingredient cyanamide per liter.

[0200] Field Testing Example E1: Table grapes in the USA Three sections of a commercial table grape orchard near Madera, California were treated during the dormant season 45 days prior to natural bud burst (February 11th) with the following spray mixture: E1-0: 600 liters per hectare of water spiked with 0.1% Break-Thru™ OE-446 E1-1: Spray mixture from example D-1 600 liters per hectare E1-18: Spray mixture from example D-18 600 liters per hectare

[0201] As a result, the vine shoots were evenly wetted. Bud burst was recorded by number 30 and 41 days after application.

[0202] Germination means the number of buds that have produced at least one leaf after n days, based on the total number of buds on the shoots at n=0 day (day of application of the spray mixture).

[0203] [Table 8]

[0204] After 30 days, germination was too early for treatment and the E1-1 treatment according to the invention was not as effective as the prior art with cyanamide (E1-18). Due to certain weather conditions, after 41 days the benefits provided by the treatment with both active ingredients were lost.

[0205] Example E2: Spanish table grapes Three sections of a table grape plantation (Red Globe type) in southern Spain were treated during the dormant period 45 days before natural bud burst (February 5th) with the following spray mixture: E2-0: 600 liters per hectare of water spiked with 0.1% Break-Thru™ OE-446 E2-1: Spray mixture from example D-1 600 liters per hectare E2-18: Spray mixture from example D-18 600 liters per hectare

[0206] As a result, the vine shoots were evenly wetted. On April 3rd, the number of bud bursts was recorded.

[0207] Germination means the number of buds that have produced at least one leaf after n days based on the total number of buds at n=0 day (day of application of the spray mixture).

[0208] [Table 9]

[0209] Thus, treatment of sodium acetylcyanamide according to the present invention is as effective as prior art treatments of cyanamide.

[0210] Example E3: Indian table grapes Three sections of Indian table grape plantations of type Bordon AR and type Hamer AR were treated with the following spray mixtures during the dormant season. E3-0: 600 liters per hectare of water spiked with 0.1% Break-Thru™ OE-446 E3-1: Spray mixture from example D-1 600 liters per hectare E3-18: Spray mixture from example D-18 600 liters per hectare

[0211] As a result, the vine shoots were evenly wetted. The number of bud bursts was recorded after 30 and 41 days, respectively.

[0212] Germination means the number of buds that have produced at least one leaf after n days based on the total number of buds at n=0 day (day of application of the spray mixture).

[0213] [Table 10]

[0214] Thus, treatment of sodium acetylcyanamide according to the present invention is at least as effective as prior art treatments of cyanamide.

Claims

1. The following applies to formula (I) and formula (II): 【Chemistry 1】 【Chemistry 2】 In the formula, R １ , R ２ , R ３ , R ４ , R ５ Groups and cations M １ , M. ２ mean, independently of one another: R １ = Hydrogen, C １ ~C ２０ Alkyl, C ３ ~C １２ Cycloalkyl, C ２ ~C ２０ Alkenyl, C １ ~C ２０ an alkoxy, aryl, alkylaryl or arylalkyl, or Q group, where Q is: Q = C, each of which is substituted with a group of formula (III) or formula (IV). １ ~C ２０ Alkyl, C ３ ~C １２ Cycloalkyl, C ２ ~C ２０ Alkenyl, C １ ~C ２０ alkoxy, aryl, alkylaryl or arylalkyl; 【Chemistry 3】 【Chemistry 4】 M １ , M. ２ = independently of each other Li, Na, K, 1 / 2Ca, 1 / 2Mg, or NR ２ R ３ R ４ R ５ and R ２ , R ３ , R ４ , R ５ = independently of each other hydrogen or C １ ~C ２０ Use of at least one compound from the group of acylcyanamides of formula (I) or (II) or their salts, which is alkyl, for regulating the reproductive growth of plants or for breaking dormancy in fruit trees.

2. R １ , R ２ , R ３ , R ４ , R ５ Groups and cations M １ , M. ２ means, independently of each other: R １ = Hydrogen, C １ ~C ２０ Alkyl, C ３ ~C １２ Cycloalkyl, C ２ ~C ２０ Alkenyl, C １ ~C ２０ an alkoxy or Q group, where Q is: Q = C, each of which is substituted with a group of formula (III) or formula (IV). １ ~C ２０ Alkyl, C ３ ~C １２ Cycloalkyl, C ２ ~C ２０ Alkenyl, C １ ~C ２０ is an alkoxy; M １ , M. ２ = independently of each other Li, Na, K, 1 / 2Ca, 1 / 2Mg, or NR ２ R ３ R ４ R ５ and R ２ , R ３ , R ４ , R ５ = independently of each other hydrogen or C １ ~C ２０ 2. Use according to claim 1, characterized in that at least one compound from the group of acylcyanamides of formula (I) or (II) or salts thereof is used, which is alkyl.

3. R １ , R ２ , R ３ , R ４ , R ５ Groups and cations M １ , M. ２ mean, independently of one another: R １ = an aryl, alkylaryl or arylalkyl, or Q group, where Q is: Q=aryl, alkylaryl or arylalkyl, each substituted with a group of formula (III) or formula (IV); M １ , M. ２ = independently of each other Li, Na, K, 1 / 2Ca, 1 / 2Mg, or NR ２ R ３ R ４ R ５ and R ２ , R ３ , R ４ , R ５ = independently of each other hydrogen or C １ ~C ２０ 2. Use according to claim 1, characterized in that at least one compound from the group of acylcyanamides of formula (I) or (II) or salts thereof is used, which is alkyl.

4. R １ Groups and cations M １ , M. ２ mean, independently of one another: 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 Q group, where Q is as follows: Q=methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, each of which is substituted with a group of formula (III) or formula (IV); M １ , M. ２ = independently of each other Na or K, 3. Use according to claim 1 or 2, characterized in that at least one compound from the group of the acylcyanamides of formula (I) or (II) or salts thereof is used.

5. 3. Use according to claim 1 or 2, characterized in that at least one compound is used which is 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.

6. As plants, as agricultural and cultivated plants or as fruit trees, the following may be included: 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 The use according to any one of claims 1 to 5, characterized in that it is for the treatment of plants selected from the group consisting of: (A. carica) or hybrid products or cultivars thereof.

7. A concentrate of a plant growth regulator for regulating the reproductive growth of a plant or for breaking dormancy in fruit trees, comprising: The concentrate is a) The following applies to formula (I) and formula (II): 【Chemistry 5】 【Chemistry 6】 In the formula, R １ , R ２ , R ３ , R ４ , R ５ Groups and cations M １ , M. ２ mean, independently of one another: R １ = Hydrogen, C １ ~C ２０ Alkyl, C ３ ~C １２ Cycloalkyl, C ２ ~C ２０ Alkenyl, C １ ~C ２０ an alkoxy, aryl, alkylaryl or arylalkyl, or Q group, where Q is: Q = C, each of which is substituted with a group of formula (III) or formula (IV). １ ~C ２０ Alkyl, C ３ ~C １２ Cycloalkyl, C ２ ~C ２０ Alkenyl, C １ ~C ２０ alkoxy, aryl, alkylaryl or arylalkyl; 【Chemistry 7】 【Chemistry 8】 M １ , M. ２ = independently of each other Li, Na, K, 1 / 2Ca, 1 / 2Mg, or NR ２ R ３ R ４ R ５ and R ２ , R ３ , R ４ , R ５ = independently of each other hydrogen or C １ ~C ２０ at least one active ingredient from the group of acylcyanamides of formula (I) or (II) or salts thereof, which is alkyl, b) at least one additive from the group of solvents, oils, surfactants or emulsifiers that is safe for agricultural purposes Including, A concentrate, said concentrate having an active ingredient concentration in the range of 100-600 g / l.

8. a) R １ , R ２ , R ３ , R ４ , R ５ Groups and cations M １ , M. ２ mean, independently of one another: R １ = Hydrogen, C １ ~C ２０ Alkyl, C ３ ~C １２ Cycloalkyl, C ２ ~C ２０ Alkenyl, C １ ~C ２０ an alkoxy or Q group, where Q is: Q = C, each of which is substituted with a group of formula (III) or formula (IV). １ ~C ２０ Alkyl, C ３ ~C １２ Cycloalkyl, C ２ ~C ２０ Alkenyl, C １ ~C ２０ is an alkoxy; M １ , M. ２ = independently of each other Li, Na, K, 1 / 2Ca, 1 / 2Mg, or NR ２ R ３ R ４ R ５ and R ２ , R ３ , R ４ , R ５ = independently of each other hydrogen or C １ ~C ２０ 8. The plant growth regulator concentrate according to claim 7, characterized in that the concentrate contains at least one active ingredient selected from the group consisting of acylcyanamides of formula (I) or formula (II) or salts thereof, which are alkyl.

9. 9. The concentrate of the plant growth regulator according to claim 7 or 8, characterized in that the concentrate is a solution, emulsion or emulsifiable solution comprising as a solvent a solvent selected from the group consisting of water, ethanol, isopropanol, glycol, polyglycol, glycerol or a mixture of these solvents.

10. 10. A concentrate of the plant growth regulator according to claim 7, characterized in that the concentrate is a solution, emulsion or emulsifiable solution which comprises as oil an oil from the group of vegetable oils.

11. The concentrate of the plant growth regulator according to any one of claims 7 to 10, characterized in that the concentrate is a solution, emulsion or emulsifiable solution containing a surfactant selected from the group consisting of nonionic surfactants as a surfactant.

12. The following applies to formula (VII) and formula (VIII): 【Chemistry 9】 【Chemistry 10】 In the formula, R １１ , R １２ The radicals and the subscripts n, m may simultaneously or independently mean: 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; 12. A concentrate of a plant growth regulator according to any one of claims 7 to 11, characterized in that the concentrate comprises, as a surfactant, a surfactant containing one or more compounds selected from the group consisting of ethoxylates of formula (VII), fatty alcohol glucosides of formula (VIII), or mixtures thereof.

13. The concentrate of the plant growth regulator according to any one of claims 7 to 12, characterized in that the concentrate is a solution, emulsion or emulsifiable solution containing an emulsifier selected from the group consisting of non-ionic emulsifiers as an emulsifier.

14. The concentrate of the plant growth regulator according to any one of claims 7 to 13, characterized in that the concentrate further comprises at least one formulation auxiliary for agricultural use, selected from the group consisting of pH adjusters, colorants, thickeners, dispersants, solubilizers, viscosity regulators, labeling agents and bittering agents.

15. The concentrate is 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 are safe for agricultural purposes, and c) at least one additive from the group of surfactants or emulsifiers that is safe for agricultural purposes Including, The concentrate has an active ingredient concentration in the range of 100 to 600 g / l. A concentrate of the plant growth regulator according to claim 7.

16. The following applies to formula (I) and formula (II): 【Chemistry 11】 【Chemistry 12】 In the formula, R １ , R ２ , R ３ , R ４ , R ５ Groups and cations M １ , M. ２ mean, independently of one another: R １ = Hydrogen, C １ ~C ２０ Alkyl, C ３ ~C １２ Cycloalkyl, C ２ ~C ２０ Alkenyl, C １ ~C ２０ an alkoxy, aryl, alkylaryl or arylalkyl, or Q group, where Q is: Q = C, each of which is substituted with a group of formula (III) or formula (IV). １ ~C ２０ Alkyl, C ３ ~C １２ Cycloalkyl, C ２ ~C ２０ Alkenyl, C １ ~C ２０ alkoxy, aryl, alkylaryl or arylalkyl; 【Chemistry 13】 【Chemistry 14】 M １ , M. ２ = independently of each other Li, Na, K, 1 / 2Ca, 1 / 2Mg, or NR ２ R ３ R ４ R ５ and R ２ , R ３ , R ４ , R ５ = independently of each other hydrogen or C １ ~C ２０ 1. A method for regulating the reproductive growth of plants or breaking dormancy in fruit trees, comprising application by dipping, brushing or spraying of the branches, shoots or buds of the plant during the dormancy of the plant with an aqueous solution comprising at least one active ingredient from the group of acylcyanamides of formula (I) or formula (II) or salts thereof, wherein the active ingredient is an alkyl.

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