DE2407143A1 - Plant-growth regulating compositions - contg N-(substd phenoxymethyl)-azole derivs - Google Patents

Abstract

Agents for influencing plant growth contain at least one azole deriv. of formula (I) (where R1 is H or phenyl; R2 is alkyl, cycloalkyl or phenyl; X is halogen, haloalkyl, alkyl, cycloalkyl, phenyl carbalkoxy, carboxy and/or NO2; n is 0-5; Y is -CO-, C=NOH or -CHOH; and Az is 1-imidazolyl, 1,2,4-trazol-1-yl or 1,2,4-triazol-4-yl). e.g. 1-(1,2,4-triazol-1-yl)-1-(2,4-dichlorophenoxy)-3,3-dimethyl-2-but- anon, or a plant-tolerated salt of such a cpd. (I) are cpds. of low toxicity which have plant growth regulating properties. The effects obtained with (I) vary according to the concentration applied and the stage of growth at the time of application, but include growth, inhibition promotion, fruit formation, latex formation, defoliation, flower-sex control, frost or drought resistance etc.

Description

Agent for regulating plant growth The present invention relates to the use of some known azole derivatives and their salts as Means for regulating plant growth.

It has already become known that some of those that can be used according to the invention Azole derivatives have fungicidal activity (cf. German Offenlegungsschrift 2 201 063).

It has also become known that N-benzyltriazoles, N-benzylimidazoles as well as Bistriazolylbisphenylmethane plant growth regulating properties (see German Offenlegungsschriften 1 949 012, 1 949 013 and 1 964 95-5).

The growth regulator effect of azole derivatives that have only one azole ring have, however, is not yet known.

It has been found that azole derivatives of the formula in which R1 represents hydrogen or phenyl, R2 represents alkyl, cycloalkyl or phenyl, X represents halogen, halogenated alkyl, alkyl, cycloalkyl, phenyl, carbalkoxy, carboxyl and / or nitro, n represents the integers 0 to 5 stands for one, Y for one or Group Az stands for the imidazolyl (1), 1,2,4-triazolyl (1) or the 1,2,4-triazolyl (4) radical, as well as their plant-physiologically acceptable salts due to their very good plant growth-regulating activity distinguish.

Surprisingly, azole derivatives which can be used according to the invention are suitable very good as a means of regulating plant growth. This was due to the known prior art by no means to be expected, because of the structurally Similar classes of compounds have hitherto only been shown to have good growth-regulating compounds Properties that contain 2 azole residues in the molecule, with either both azole residues are linked to the rest of the molecule via the 1-position of the azole ring, or but one azole residue over the 1 undulation and another over the 2-position of the azole ring is connected to the rest of the IvIolekülteil. So it was obvious that the growth-regulating effectiveness of such compounds by the presence of two azole rings in the molecule. - Since the usable according to the invention Substances have a low toxicity and are easy to handle they represent a valuable addition to technology.

The azole derivatives to be used according to the invention are represented by the formula (I) precisely defined and some are known (cf. German Offenlegungsschriften 2 105 490 and 2 201 063).

The compounds of the formula not yet described in the literature (I) are the subject of separate patent protection requests (see German patent applications P 2,324,010; P 2,325,156; P 2,333,354; P 2333355; P 2334352; P (Le A 15 410); P. Jte A 15 4117).

In the formula (I), R1 is preferably hydrogen or phenyl, R2 preferably for straight-chain or branched alkyl with up to 4 carbon atoms, also for cycloalkyl with 5 to 7, in particular with 6 carbon atoms, or for Phenyl. X in the formula (I) is preferably halogen, in particular chlorine, Bromine or fluorine, for haloalkyl with 1 to 2 carbon atoms and 2 to 5 halogen atoms, in particular fluorine, furthermore for straight-chain or branched alkyl with 1 to 4 carbon atoms, for cycloalkyl with 5 to 7, in particular with 6 carbon atoms, also for varbalkoxy with 1 to 3 carbon atoms in the alkoxy radical, also for the phenyl, carboxyl and / or the nitro radical; n stands for the numbers 0 to 5, in particular represents 0 to 3. Y is preferably the carbonyl group, CO, the secondary alcohol group - CHOH or for the oximinocarbonyl group ~ C = NOH, and Az preferably stands for the imidazolyl (1), the 1,2,4-triazolyl (1) and the 1,2,4-triazolyl (4) radical.

The salts of azole derivatives of the formula (I) are those with those which are tolerated by plants Acids in question. Examples of such acids are the hydrohalic acids, such as hydrochloric acid or hydrobromic acid, but especially hydrochloric acid, also phosphoric acid, nitric acid, Sulfuric acid, still aliphatic Mono- and dicarboxylic acids and hydroxycarboxylic acids, of which, for example, acetic acid, Sorbic acid, maleic acid, fumaric acid, succinic acid, lactic acid, and tartaric acid Citric acid may also be mentioned, as well as aromatic carboxylic acids such as, for example, selioyl acid or 1,5-naphthalene disulfonic acid.

Examples of the active ingredients which can be used according to the invention are specifically mentioned: 1-E '2', 4'-Triazolyl- (1 ') 7- (2', 4'-dichlorophenoxy) -3,3-dimethyl-butan-2-one and its hydrochloride 1-J '2', 4'-triazolyl- (1 7] -1- (4'-chlorophenoxy) -3,3-dimethylbutan-2-one and its hydrochloride, sulfate or nitrate 1-g ', 2', 4'-triazolyl- (1 '7-1- (2'-chlorophenoxy) -3,3-dimethylbutan-2-one i- [1'2 ', 4'-Triazolyl- (1'] - 1- (4'-nitrophenoxy) -3,3-dimethyl butan-2-one [1 ', 2', 4'-triazolyl- ( 1' ] -1- (4'-chlorophenoxy) -1-phenyl-3,3-dimethyl-butan-2-one 1- / T ', 2', 4'-triazolyl- (1 ' )] 7-1- (4'-carboxyphenoxy) -3,3-dimethyl-butan-2-one 1- ', 2', 4'-triazolyl- (1 'g-1- (4t-methoxy carbonylphenoxy) -3 , 3-dimethyl-butan-2-one 1-1'2 ', 4'-Triazolyl- (4') 7-1- (2 ', 4''5'-trichlorophenoxy) -3,3-dimethyl-butan-2-one [1 -', 2 ', 4'-Triazolyl- (1')] - 1- (4'-fluorophenoxy) -3,3-dimethylbutan-2-one 1-[ r, 4'-Triazolyl- (1 ') 7-1- (4'-fluorophenoxy) -3,3-dimethyl-2-hydroxy butane 1c-111>' '41 Trjnüiyi (1') J-1 (2 ', 4'-dichloroptienoxy) -3,3-dimc ethyl-2-hydroxy-butane 1-j '2 "to 4', 4'-triazolyl- (1 -1-phenoxy-3,3-dimethyl-2-hydrox4ybutyne 1- / 1 '2' 4 '-triazolyl- (1') -1- (4'-cyclohexylphenoxy) -3,3-dimethyl-2-hydroxy-butane 1 - {Imidazol- (1 ') 1-1 -phenoxy-3'3 -dimethyl-2-hydroxy-butane 1 [imidazolyl- (1' (4'-fluoropheoxy) -, 5-dimethyl-2-hydroxybutane 1- [imidazolyl- (1 imidazolyl- (1 ') 7-1- (2', 4'-dichlorophenoxy) -3,3-dimethyl-2- hydroxy-butane.

Some of the substances that can be used according to the invention are new, but they can be produced in a simple manner by processes that are known in principle. They are obtained, for example, by using azole derivatives of the formula in which X, R2, Az and n have the meanings given above, reduced by generally customary methods. The reduction can be carried out, for example: a) with hydrogen in the presence of a catalyst, such as for example Kaney-ickel, and in the presence of a polar solvent, such as methanol, at a temperature between 2000 and 5000, or b) with aluminum isopropoxide in the presence of a inert solvent at a temperature between 20 ° C. and 1200 ° C. and subsequent hydrolysis, or c) with complex hydrides, such as sodium borohydride or lithium alanate, in the presence of a polar solvent, for example methanol, at temperatures between OOC and 300 ° C. and subsequent hydrolysis, for example with aqueous hydrochloric acid, or d) with formamidinesulfinic acid and alkali metal hydroxide, such as sodium hydroxide, in aqueous solution at temperatures between 200 ° C. and 10,000 and in the presence of a polar solvent such as ethanol.

The compounds of the formula (I) thus obtained are made according to the customary Methods isolated and, if necessary, purified. For example, the work-up be carried out by distilling off the reaction mixture, if necessary beforehand the solvent is mixed with water and then with an organic solvent, such as ethyl acetate or methylene chloride, extracted and then the organic phase is separated off, dried and concentrated. The residue that remains is optionally purified by recrystallization or salt formation.

The compounds of the formula (II), which are used as starting materials for the preparation the active ingredients which can be used according to the invention are required are, are known or can be synthesized by known methods.

Some of the previously unknown active ingredients which can be used according to the invention can be represented using other methods described above (cf. German Offenlegungsschrift 2 201 063). The isolation of the reaction products is characterized here by that one obtained after the usual work-up residue of a fractionated Subjects to crystallization, using low-boiling solvents, such as Ethyl acetate, diethyl ether or petroleum ether are used. The new 1,2,4-triazolyl- (4) -compounds are thus in good purity in addition to the known 1,2,4-triazolyl (1) compounds obtain.

The salts of the compounds of the formula (I) can also be used in simple way to represent by customary methods of salt formation. You will for example obtained by dissolving the base in ether, for example DlGthyläther, and the acid, for example hydrogen chloride, is added. The crystalline precipitates Salts are isolated by filtering off and can optionally then be purified by recrystallization.

The active ingredients which can be used according to the invention have a physiological effect Occurrence of plant growth and can therefore be used as plant growth regulators be used.

The various effects of the active ingredients depend essentially on them from the time of application, based on the development stage of the seed or the plant as well as the concentrations used.

Plant growth regulators are used for various purposes, which are related to the stage of development of the plant.

With the substances that can be used according to the invention, growth can be achieved of the plants strongly. This growth inhibition is of interest in the case of grasses reduce the frequency of grass clippings. An inhibition of vegetative growth also plays an important role with grain, as it reduces or reduces storage can be completely prevented.

In many cultivated plants, the inhibition of vegetative growth allows a denser planting of the culture, so that an increased yield based on the soil area can be achieved.

Another mechanism of increasing yield is based on growth inhibitors on the fact that the nutrients benefit to a greater extent the formation of flowers and fruits come while vegetative growth is restricted.

The substances that can be used according to the invention can also be used to promote achieve vegetative growth. This is of great use when the vegetative Plant parts are harvested. However, vegetative growth can be promoted also at the same time lead to a promotion of generative growth, so that e.g. more or larger fruits come to the training.

Under the influence of the active ingredients it can lead to the formation of parthenocarp Fruits come. The sex of the flowers can also be influenced.

With the active ingredients which can be used according to the invention, the Influence the production or the outflow of phytochemicals in a positive way. An example is the stimulation of the latex flow in rubber trees.

During the growth of the plant there may also be lateral branching increased by a chemical break in the apical dominance. It insists Interest, e.g. in the propagation of plants. In concentration-dependent However, it is also possible to inhibit the growth of the side shoots, e.g. in order to increase the development of side shoots in tobacco plants after decapitation prevent and thus promote leaf growth.

The influence of the active ingredients on the leaf structure of the plants can can be controlled so that defoliation is achieved, e.g. to facilitate harvesting or to decrease transpiration at a time when the plant is transplanting shall be.

Premature fruit fall can be prevented under certain conditions or the fruit fall in the sense of a chemical thinning up to a certain one Promote extent. The promotion of fruit fall can, however, also be exploited that the treatment is carried out at the time of harvest, thereby facilitating harvesting entry.

The active ingredients which can be used according to the invention can also be used Accelerate or delay fruit ripening and improve fruit development. A temporal concentration of the fruit ripeness is also possible. The desired Effects can be achieved by varying the applied concentration of Active ingredients and by application at different times during the plant's development achieve.

With the substances that can be used according to the invention, frost and drought resistance can be achieved induced in the plants.

The seed or bud dormancy of the plants, i.e. the endogenous annual rhythm, can be influenced by the active ingredients, so that the plants e.g. at a point in time germinate, sprout or bloom when they are normally unwilling to do so demonstrate.

With the active ingredients can also be achieved that the sprouting of Buds or the germination of seeds is delayed, e.g. in areas at risk of frost to avoid damage from late frosts.

The active ingredients which can be used according to the invention can be converted into the customary ones Formulations such as solutions, emulsions, suspensions, powders, Pastes and granulates. These are prepared in a known manner, for example by mixing the active ingredients with extenders, i.e. liquid solvents, are under pressure liquefied gases and / or solid carriers, if necessary using of surface-active agents, i.e. emulsifiers and / or dispersants and / or foam-generating agents. In the case of using water as an extender For example, organic solvents can also be used as auxiliary solvents. The following liquid solvents are essentially: aromatics, such as xylene, Toluene, benzene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic Hydrocarbons such as chlorobenzenes, chloroethylene or methylene chloride, aliphatic Hydrocarbons such as cyclohexane or paraffine, e.g. petroleum fractions, Alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone Methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, and water; with liquefied gaseous Extenders or carriers are liquids that are meant to be used in normal Temperature and under normal pressure are gaseous, e.g. aerosol propellant gases such as halogenated hydrocarbons, e.g., freon; as solid carrier materials: natural rock flour, such as kaolins, clays, Talc, chalk, quartz, attapulgite, montmorillonite and diatomaceous earth, and synthetic Ground rock, such as finely divided silica, aluminum oxide and silicates; as emulsifying and / or foam-generating agents: nonionic and anionic emulsifiers, such as Polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. alkylaryl polyglycol ethers, Alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolysates; as a dispersant: e.g. lignin, sulphite waste liquors and methyl cellulose.

The active ingredients which can be used according to the invention can be used in the formulations in a mixture with other known active ingredients, such as fungicides, insecticides and acaricides.

The formulations generally contain between 0.1 and 95 percent by weight Active ingredient, preferably between 0.5 and 90 percent by weight.

The active ingredients can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, emulsifiable Concentrates, emulsions, foams, wettable powders, pastes, soluble powders, Dusts and granules. The application splinted in the usual Way, e.g. by pouring, spraying, Spray, scatter, Dusting, etc.

The active ingredients which can be used according to the invention are generally at Active ingredient concentrations between 0.0001 and 0.05 / ó sufficiently effective. In the The use of aqueous active ingredient preparations can reduce the active ingredient concentrations fluctuate in larger areas. They are then approximately between 0.0005 and 2.0 yó.

If the active ingredients are applied using special application methods, e.g. according to the ULV (ultra-low-volume) process, this is how the substance concentrations are higher, e.g. between 20 and 80%.

In general, 0.01 to 20 kg are used per hectare of soil, preferably 0.1 to 10 kg of active ingredient.

For the application time, the use of the growth regulators applies is carried out in a preferred period, the exact delimitation of which is based on the climatic and vegetative conditions.

The substances that can be used according to the invention are not only very good plant growth regulating properties, but also have also acaricidal and microbicidal effectiveness.

In the following examples, the activity is according to the invention usable substances shown as growth regulators, without the possibility of further Exclude applications as growth regulators.

Example A Growth influencing / bean solvent: 10 parts by weight Methanol emulsifier: 2 parts by weight of polyethylene oorbitan monolaurate 1 part by weight of active ingredient is mixed with an appropriate active ingredient preparation the specified amounts of solvent and emulsifier and fill with water on the desired focus on.

Young bean plants about 10 cm high are mixed with the active compound preparations sprayed until drained. After 14 days, the increase is measured and expressed in v / O. where 0 f'o means the standstill of growth and 100% 0 means growth that corresponds to the person corresponds to the untreated control plants.

Active ingredients, active ingredient concentrations and results are shown in Table A below: Table A Influencing growth / beans Active ingredient Concentration Increase Comments tration in Water 0 100 (Control) CH3 Cl t -O-CH-CO - »- CH3 0.05 45 gNfl CH3 (12) CH Cl e -O-CH-CO-7 -CM3 0.05 ° branched CHJ x H2S04 (30) VH O-CH-CO- '3 Cl0-C1H-C0-C1-CH3 0.05 65 N OH m3 x ENT (31) 3 Table A (continued) Controlling growth / beans Active ingredient concentration increase remarks (in vp) (in; 0) Oh dark / CH3 green, Br X O-CH-CH-C \ CH3 0.05 65 sheets size II Ir NI (4) Cl n O-CH-CO- I 0-C1H-C0-C1-CH3 0.05 35 branched N OH3 3 (22) CH i3 HOOCO-fH-CO-C-CH3 0.05 115 CH, (24) Table A (continued) Controlling growth / beans Active Ingredient Concentration Increase Comments tion (in a10) (in ) OH 02Ne0- | H-CO-C-CHD 0.05 140 N CH3 3 (20) Q / 3 C oc-co-c-cK, 0.05 55 dark green - 1 3 sheets N nu CH3 (23) 2 9 H3 OC-CO-C-CH3 0.05 10 OH3 (32) x HOl NOH CH3 02N-O-CX-C-CCH3 0.05 60 OH3 N (14) Table A (continued) Active ingredient concentration increase remarks (in%) (in 0) N \\ 0H / CH3 Cl 9 -O-CH-CC-CH 0.05 50 Z / 1 7 N CH in (17) C1 \OH OH-CO-C-CH7 0.05 140 Cl (| CH3 Wt (8th) OH CH / 3 FO-CH-CH-C-CH, 0.05 70 sheets 3 - t deformed 1NN OH3 N <CH3 (17) Cl OH OH C1-J-3- 0.05 60 dark green Cl O-CH-CH-C-CH 1 60 dark green I deformed N CH3 leaves (19) pa Table A (continued) Active ingredient concentration increase remarks (in) (in%) OH OH3 II F <-O-XEI-CH-C-CH3 0.05 110 CH (18) II OH 3 a O-CH-CH-C-CH3 0.05 70 N CH (1) OH CH3 O-CH-HC-CH, 0.05 80 N CH OH (16) m3 OH OH 1/3 -OH-CH-C-CH3 0.05 100 dark green - (3 sheets N OH3 fqT (15) Example B Growth inhibition / wheat Solvent: 10 parts by weight of methanol Emulsifier: 2 parts by weight of polyethylene sorbitan monolaurate To produce a suitable preparation of active ingredient, 1 part by weight of active ingredient is mixed with the stated amounts of solvent and emulsifier and made up to the desired concentration with water.

Young, 5-8 cm high wheat plants are treated with the preparation of the active compound sprayed dripping wet. After 14 days, the growth is measured and the inhibition of growth compared to the untreated control plants expressed in ffi. It means 100 % 0 the standstill of the growth and 0% 0 a growth that corresponds to that of the untreated Control plants.

Active ingredients, active ingredient concentrations and results are shown in Table B below: Table B Growth inhibition / wheat Active ingredient concentration inhibition of growth (in) (in k> water (Control) 0 0 OH C1 O-CH-CO-C-CH, 0.05 45 N> N CH3 (12) Nu CH Cl <-O-fH-CO-C-CH 0.05 15 1 \ 3 OH N (31) x HN03 OH OH CH, OC - (/ O-CS-CH-C-CH3 0.05 30 (25) O; iötNi OH3 Table B (continued) Active ingredient concentration inhibition of growth (in%) (in Xo) CH3 02N0- I-CO- ^ - CH3 0 05 1 5 (20) CH3 (20) NOH CH CloO-CH-C-tv-CH 0.05 20 3 N CH3 3 I. (13) OH CH 1/3 y 0-C1H-CH-% CH3 0.05 15 z / I CH # (17) OH y) H3 3-o-fH-0H- -0H3 0.05 35 I. (16) G. Example C Growth Influence / Barley Solvent: 10 parts by weight of methanol Emulsifier: 2 parts by weight of polyethylene sorbitan monolaurate To produce an appropriate preparation of active ingredient, 1 part by weight of active ingredient is mixed with the stated amounts of solvent and emulsifier and made up to the desired concentration with water.

Young barley plants, 5-8 cm high, are treated with the preparation of the active compound sprayed dripping wet. After 14 days, the increase is measured and expressed in ffi. Here 0% 0 means the standstill of growth and 100 ffi a growth that corresponds to that one corresponds to the untreated control plants.

Active ingredients, active ingredient concentrations and results are shown in Table C below: Table C Influencing growth / barley Active ingredient concentration increase remarks (in yo) (in%) Water 0 100 0 i00 (Control) OH Cl / 3 -0-CH-C0-C-CH 0.05 1 05 I \ 3 0.1 130 N OH3 (12) currently Cl C1J-O-CH-CO-CH, 0.05 75 I. NH x HOl (34) OH / CH3 CH30-1Cl | I / 0.05 50 1 C \ CH3 0 1CH3 (25) Table C (continued) Active ingredient concentration increase remarks (in%) (in to OH HOOCQ 0-CH-CO-C-CH3 0.05 45 , N CH3 3 (24) N11 CH / 3 02N e -O-IH-CO-C-CH3 0.05 80 1 3 N CH7 (20) 11K ß W / 3 / cm3 80 .CH 0.05 3 OH3 (32) | u x HOl OH H3 FO-CH-OH-C-CH3 0.05 80 larger Straw N CH3 strength (18) Table C (continued) Active ingredient concentration increase remark (in) (in so) ? H -o-1CH-CH-z-CH3 0S05 70 z / 0.05 N OH3 (16) S CH3 Example D Growth influencing / chrysanthemums Solvent: 10 parts by weight of methanol Emulsifier: 2 parts by weight of polyethylene sorbitan monolaurate To produce an appropriate preparation of active ingredient, 1 part by weight of active ingredient is mixed with the stated amounts of solvent and emulsifier and made up to the desired concentration with water.

10 cm high earysanthemum cuttings are mixed with the active ingredient preparations sprayed dripping wet. After 3 weeks, the increase is measured and expressed in%. Here 0% means the standstill of growth and 100 ffi a growth that means that corresponds to the untreated control plants.

Active ingredients, active ingredient concentrations and results are shown in Table D below: Table D Influencing growth / chrysanthemums Active ingredient concentration increase (in%) (in%) Water 0 100 (Control) Cl OH Cl CO-KCH33 0.1 80 OH3 - (11) N1 H3 C144-CH-CO-C-CH3 0.1 50 N CH3 (12) mm4 1 ClO-CIH-CO-CH3 0.1 85 N (34) xx HOl Table D (continued) Active ingredient concentration increase (in P) (in d) CH3 02N-O-CH-C0-KCH} 0.1 120 N CH (20) QCH, Cl-O-C-C0-KCH3 0.1 110 rNs CH3 (23) Xl X Chemical preparation examples Example 1 Method a) In a solution of 25.8 g (0.1 mol) of 1-phenoxy-1- / imidazolyl- (1 'g-3,3-dimethylbutan-2-one in 250 ml of methanol) are stirred and refluxed at 5 to 1000 portions 5.9 g (0.15 mol) of sodium borohydride were added. After stirring for 15 hours at room temperature, 20 ml of concentrated hydrochloric acid are added. The reaction mixture is stirred for a further 15 hours at room temperature and then poured into 300 ml of saturated sodium hydrogen carbonate solution extracted twice with 100 ml of ethylene chloride each time, the organic phase was washed twice with 100 ml of water each time, dried over sodium sulfate and the solvent was distilled off in a water jet vacuum.

The remaining residue is digested with 30 ml of petroleum ether.

21.6 g (83/10 of theory) of 1-phenoxy-1- / imidazolyl- (1 ' 7-3,3-dimethyl-2-hydroxy-butane, melting point 99-1050C.

(Mixture of erythro and threo form) method b) 12.3 g (0.048 mol) 1-Phenoxy-1- / imidazolyl- (1) 7-3,3-dimethylbutan-2-one are dissolved in 50 ml of anhydrous Ether dissolved. These Solution becomes a suspension of 2.6 g (0.07 Mol) lithium aluminum hydride in 80 ml of anhydrous ether was added dropwise.

The resulting reaction mixture is refluxed for one hour heated and left to stand overnight. Then the reaction mixture is under Ice cooling, water is added dropwise to remove excess lithium aluminum hydride to destroy. The reaction mixture is then poured into a cold 20 percent aqueous solution Caustic soda entered. It is extracted twice with 100 ml of ether each time, and the dried organic phase over sodium sulfate and the solvent is distilled under reduced pressure Pressure off. The remaining oil is boiled with petroleum ether. The one that crystallizes out The precipitate is filtered off from the hot solution.

1.6 g (13 ffi of theory) of erythro-1-phenoxy-1-imidazolyl- (1 ' ) 7-2-hydroxy-3,3-dimethylbutane with a melting point of 125 ° C.

When the filtrate cools down, a precipitate is formed again is filtered off. This fraction gives 1.4 g (11% of theory) of threo-1-phenoxy-1-eimidazolyl- (1 g-2-hydroxy-3,3-dimethyl-butane, melting point 106-1070C.

Example 2 In a solution of 31.4 g (0.1 mol) of w- [4'-chlorophenoxy] - w- [1,2,4-triazolyl- (1 ')] - acetophenone in 300 ml of methanol are added with stirring and iiiskühlung 5 g (0.08 mol) of sodium borohydride added in portions. The reaction mixture is stirred for one hour at room temperature. The solvent is then distilled off in vacuo, the residue that remains is taken up in dilute hydrochloric acid, the solution is briefly heated and filtered. The filtrate is then made alkaline with sodium hydroxide solution. The resulting precipitate is filtered off and taken up in ethyl acetate. After the ethyl acetate has been distilled off, an oil remains which crystallizes on digestion with ligroin. After redissolving from ligroin / isopropanol, 25 g (98/0 of theory) 1- (4'-chlorophenoxy) -1- 2 '4'- triazolyl- (12-2-phenyl-2-hydroxy-ethanol with a melting point of 1170C.

Representation of the preliminary product A solution of 32.5 g (0.1 mol) of bromo-O- (4'-chlo-phenoxy) -acetophenone and 30 g (0.44 mol) of 1,2,4-triazole in 240 ml of acetonitrile becomes 48 Heated under reflux for hours. The solvent is then distilled off and the residue that remains is taken up in 800 ml of water. The aqueous solution is extracted several times with methylene chloride and the organic phase is washed twice with 200 ml of water each time. The organic phase is then dried over sodium sulfate and concentrated under reduced pressure. The remaining residue, which can be redissolved from a mixture of ligroin / isopropanol = 2: 1, crystallizes. The melting point is between 98 and 1000V.

The ti) -Bromo-43 required as the starting material for the preliminary product - (4 '-chlorphenoxy) -acetophenone is brominated by the during the condensation of 4-chlorophenol with; -chloroacetophenone resulting 0- (4'-chloro-phenoxy) -acetophenone made in the usual way. It has a melting point of 7100.

Example 3 In a solution of 587 g (2 mol) of 1- (4'-chlorophenoxy) -1-T '2', 4'-triazolyl- (1 -3'3-dimethyl-butan-2-one in 3 liters of methanol 80 g (2 mol) of sodium borohydride in portions of 5 g each are added at 0 to 1000 with stirring and ice cooling. The reaction mixture is first stirred for 2 hours at room temperature and then for a further 12 hours and then 300 g (3 mol) of concentrated aqueous hydrochloric acid are added in such a way that the temperature of the reaction mixture is kept between 10 and 20 ° C. The resulting suspension is stirred for 6 hours at room temperature and then mixed with a solution of 400 g (4th , 8 mol) of sodium hydrogen carbonate in 3.8 l of water are added, the precipitate which separates out is filtered off, giving 502 g (85 gO of theory) of 1- (4t-chlorophenoxy) -1- [1 '2', 4'-triazolyl - (1 ')] 7-3,3-dimethyl-2-hydroxybutane, melting point 112 to 1170C.

Example 4 In a solution of 33.6 g (0.1 mol) of 1- (4'-bromophenoxy) -1-1 '2', 4'-triazolyl- (1 ') / -3,3-dimethyl-butan-2 -on in 300 ml of ethanol, a solution of 8 g (0.2 mol) of sodium hydroxide in 40 ml of water and 32.4 g (0.3 sol) of formamidinesulfinic acid are added one after the other. The reaction mixture is refluxed for 3 hours, then filtered and finally concentrated by distilling off the solvent under reduced pressure. The oily residue is taken up in 100 ml of water and the resulting solution is extracted twice with 100 ml of methylene chloride each time. The organic phases are combined, washed twice with 100 ml of water each time, then dried over sodium sulfate and evaporated by distilling off the solvent under reduced pressure. The remaining oil crystallizes on boiling with petroleum ether. The crystalline product is filtered off and dried. 26.5 g (79 ffi of theory) of 1- (4'-bromophenoxy) -1-f1 ', 2', 4'-triazolyl- (1 '-3,3-dimethyl-2-hydroxy-butane from Melting point 115-118 ° C.

Example 5 A solution of 116 g (0.3 mol) of 1- (2 ', 4t, 6'-trichlorophenoxy) -1-bromo-3,3-dimethyl-butan-2-one in 240 ml of anhydrous acetonitrile is added with stirring Then 72 g (1.25 mol) of 1,2,4-triazole were added. This reaction solution is refluxed for 48 hours and then concentrated by distilling off the solvent under reduced pressure. The residue is taken up in 200 ml of water and the resulting solution is extracted twice with 250 ml of methylene chloride each time. The combined organic phases are washed three times with 100 ml of water each time, then dried over sodium sulfate and evaporated by distilling off the solvent under reduced pressure. The remaining crystalline residue is boiled in 153 ml of ethyl acetate. The undissolved product is filtered off and dried.

18.6 g (17 ffi of theory) 1- ', 2', 4'-triazolyl) - (4 ') g-1- (2', 4 ', 6'-trichlorophenoxy) -3,3- are obtained dimethyl-butan-2-one from melting point 21900.

The filtrate (ethyl acetate solution) is removed by stripping off the solvent concentrated under reduced pressure, and that accruing residue is boiled with petroleum ether. The product that remains undissolved becomes filtered off and dried. 61.2 g (56 ß of theory) 1- [1 ', 2', 4 * -triazolyl- (1 g-1- (2 ', 4', 6'-trichlorophenoxy) -3,3-dimethylbutan-2-one, melting point 91-93 ° C.

In a corresponding manner, the compounds are obtained in the Table 1 below in Examples 6-28.

Table 1 At- game X n R1 R2 Y Az melting point No. 0 6 2'4Cl2 2 HC (CH3) 3 CO N 145 (Ether residue) 7 4-NO2 1 HG (CH3) 3 CO N 174-176 | back NN stood) 8 2 4,5-C13 3 HC (0H3) 3 CO N. 208-210 g V (ethyl acetate Residue) 9 4-C6H5 1 HC (CH3) 3 CO N 212 (Ligroin Residue) Continuation table At- game X n R R2 Y Az SchmelO- No. point 0 10 4-Br 1 HC (CH 3) 3 CO N 171 Fii (ligroin- Residue) 11 2,4-C12 2 HO (CH3) 3 CO,? 65 12 4-C1 1 HC (CH3) 3 CO (t 75 3'3 1 13 4-C1 1 HC (CH3) 3 C = NOH ß 194-205 14 4-NO2 1 HC (CH3) 3 C = NOH N> g 187 15 S 0 H 3) 3 -CHOH N 88-94 fY 16 1 1 H (cm,) 3 -CHOR T 1 1 5-120 17 4-F 1 H 0 (0113) 3 -CHOH 99-110 N N Table 1 continued At- R2 stem X n R r RY Az ochmelz- point C I. 15 4-F 1 H 'S (CH 3) 3 CHOH N 103-105 1, 4- ^ 12 2 HC (CH3) 3 -CHOX C) N 101-10'3 q 2 1 HC (CH3) 3 C3 q i $ D) 21 4-3 1 X 0 (0113) 3 (3) 3 (3 115-118 ½ 22 2-vl 1 XC (CH3) 3 CO N 68 ~ rjcj 23 4-Cl 1 OC (CXI3) 3 ao NsN 130 Ül " 4-00011 1 11 C (CH3) 3 CO N i 1etc37 Table 1 continued At- game X n R1 R2 Y Az Schmel- No. point C 25 4-COOCH3 1 H a (aH3) 3 OHOH SN> 136-138 N 26 3-CF3 1 H 0 (0113) 3 Co NsN 74-75 / 3 N II 27 4-C (CH3) 3 1 HC (CH3) 3 CO N 115 28 4-C (CH3) 3 1 HC (CH,) sj -CHOH AN 113-117 The salts listed in Table 2 below in Examples 29 to 33 are obtained by reacting bases of the formula (I) with the corresponding acids.

Table 2 x acid At -2 game X n R1 RY Az Acid SchmelO- No. point C v 29 2,4-Cl2 2 11 0 (0113) 3 CO to N 125-127 30 4-C1 1 HC (CH3) 3 CO N H2S04 11 141 2S04 31 4-Cl 1 HC (CH3) 3 CO N HIN03 140 AN3 32 Cl2 2 0 (0113) 3 CO N HC1 133-138 Ä'N 33 4-C (CH 1 H 0 (0113) 3 CO N HCl 140 ½ 34 2,4-Cl2 2 H CH3 CO N = N HC1 125-131 \\ mi

Claims (5)

Claims means for influencing plant growth, characterized by a content of at least one azole derivative of the formula in which R1 stands for hydrogen or phenyl, R2 stands for alkyl, cycloalkyl or phenyl, X stands for halogen, haloalkyl, alkyl, cycloalkyl, phenyl, carbalkoxy, carboxyl and / or nitro, n stands for the integers 0 to 5, Y for one or Group and Az stands for the imidazolyl (1), 1, 2,4-triazolyl (1) or the 1, 2,4-triazolyl (4) radical, or a vegetable-compatible salt of these compounds. 2. Means for inhibiting plant growth and for influencing it of the habitus of higher plants, characterized by a content of azole derivatives according to claim 1. 3. A method for influencing plant growth, characterized in that that one azole derivatives according to claim 1 on the Plants or theirs Habitat eirwirE: en loud. 4. Use of azole derivatives according to claim 1 for influencing of plant growth. 5. Process for the production of an agent for influencing plant growth, characterized in that azole derivatives according to Claim 1 are mixed with extenders and / or surfactants mixed together.