DE3922770A1 - Agricultural use of azolyl:methyl-oxirane derivs. - Google Patents

Abstract

Azolylmethyloxiranes of formula (I) or their salts, are used as herbicides, R1 = H or halogen, R2 and R3 = (a) 1-8C alkyl opt. substd. by dioxyanyl or phenyl, where phenyl, is opt. substd. by 1-5 halogen atoms, and/or 1-3 of 1-4C alkyl, 1-4C haloalkyl, 1-4C alkoxy, and 1-4C haloalkoxy, (b) 3-8C cycloalkyl, 5-8C cycloalkenyl, tetrahydropyranyl or norbornyl, opt. substd. by 1-3 of 1-4C alkyl and halogen or (c) phenyl, biphenylyl, naphthyl or pyridyl, opt. substd. by 1-5 halogen atoms and/or 1-3 of 1-4C alkyl, 1-4C haloalkyl, 1-4C alkoxy, 1-4C haloalkoxy, OPh, SO2Ph, NH2, mono- or di(1-4C alkyl) and NO2, X = N or CH.

Description

The present invention relates to plant growth regulators, containing azolylmethyloxiranes of the general formula I.

in which the substituents have the following meaning:
R¹ is a halogen atom,
R², R³ C₁-C₈-alkyl, which can carry one of the following radicals: dioxanyl or phenyl, where the phenyl radical in turn can carry one to five halogen atoms and / or one to three of the following groups: C₁-C₄-alkyl, C₁-C₄ -Haloalkyl, C₁-C₄-alkoxy and / or C₁-C₄-haloalkoxy,
C₃-C₈-cycloalkyl, C₅-C₈-cycloalkenyl, tetrahydropyranyl or norbornyl, where these cyclic radicals can carry one to three of the following substituents: C₁-C₄-alkyl and / or halogen,
Phenyl, biphenyl, naphthyl or pyridyl, where these aromatic radicals can carry one to five halogen atoms and / or one to three of the following substituents: C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄- Haloalkoxy, phenoxy, phenylsulfonyl, amino, C₁-C₄-alkylamino, di-C₁-C₄-alkylamino and / or nitro,
X nitrogen or a methine group CH
or their environmentally compatible salts.

The invention also relates to methods of using these agents.

DE-A 35 63 529 and EP-A 94 564 describe those defined at the outset Azolylmethyloxirane I as a fungicide.

The object of the present invention was to regulate new plant growth Find means.  

According to this task it was found that the beginning defined azolylmethyloxirane I for influencing plant growth own.

The azolylmethyloxiranes I are obtained by generally known methods (e.g. DE-A 35 63 529 and EP-A 94 564).

Compounds I are obtained particularly advantageously by reacting a Epoxyaldehyde II with an N-methyl azole derivative III in the presence of a Halogenating agent (Hal).

Suitable halogenating agents are phosphorus halides such as phosphorus trichloride, Phosphorus tribromide, phosphorus pentachloride and phosphorus oxyhalides such as phosphorus oxytrichloride and thionyl halides such as Thionyl chloride and thionyl bromide.

The reaction is usually carried out in the presence or absence of an aprotic organic solvents at temperatures from -30 ° C to 80 ° C, in particular 0 ° C to 30 ° C, performed.

It is preferred to work without solvents or in aprotic ones Solvents such as pentane, hexane, decalin, toluene, methylene chloride, Chloroform, carbon tetrachloride, dichloroethane or equivalent Mixtures.

The compounds of formula I contain asymmetric carbon atoms and can therefore occur as enantiomers and diastereomers. The mixtures of diastereomers can be customary in the compounds of the invention Way, for example due to their different solubility or separate by column chromatography and isolate in pure form. The Racemates can be prepared in the compounds according to the invention by known Methods, for example by salt formation with an optically active Acid, separation of the diastereomeric salts and release of the enantiomers separate using a base. Suitable as growth regulators both the uniform diastereomers or enantiomers as well as their the resulting mixtures.  

Acid addition salts are, for example, the hydrochlorides, bromides, sulfates, Nitrates, phosphates, oxalates or dodecylbenzenesulfonates. The effectiveness the salt is due to the cation, so that it is based on the anion i. a. does not arrive. The active ingredient salts according to the invention are produced by reacting the azolylmethyloxiranes with the acids.

With regard to their use as growth regulators, azolylmethyloxiranes I are particularly suitable, in which the substituents have the following meanings:
R¹ is a halogen atom such as fluorine, chlorine, bromine and iodine, in particular chlorine and bromine,
R² is an alkyl group such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3- Dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1- methylpropyl and 1-ethyl-2-methylpropyl, especially 1-methylethyl and 1,1-dimethylethyl,
this alkyl group can preferably be substituted in the 1-, 2- or 3-position by one of the following radicals: 1,3-dioxan-2-yl, 1,3-dioxan-4-yl, 1,3-dioxan-5 -yl and 1,3-dioxan-2-yl, in particular 1,3-dioxan-2-yl or phenyl, which in turn contains one to five of the halogen atoms mentioned under R¹, in particular phenyl,
and / or can carry one to three of the following groups: alkyl having 1 to 4 carbon atoms as mentioned above, in particular methyl,
Haloalkyl such as fluoromethyl, difluoromethyl, trifluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl, trichloromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2- Dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl, especially trifluoromethyl,
Alkoxy such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy and 1,1-dimethylethoxy, especially methoxy,
and / or haloalkoxy such as difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, dichlorofluoromethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-1 , 1,2-trifluoroethoxy and pentafluoroethoxy, especially trifluoromethoxy,
a cycloalkyl group such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl, in particular cyclohexyl,
a cycloalkenyl group such as 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1-cycloheptenyl, 2-cycloheptenyl, 3-cycloheptenyl, 4-cycloheptenyl, 1-cycloocotenten , 3-cyclooctenyl and 4-cyclooctenyl, especially 3-cyclohexenyl,
a tetrahydropyranyl radical such as 2-tetrahydropyranyl, 3-tetrahydropyranyl and 4-tetrahydropyranyl, in particular 4-tetrahydropyranyl,
a norbornyl radical such as 2-norbornyl,
wherein the above-mentioned cyclic radicals one to three of the above-mentioned alkyl groups, especially methyl
and / or halogen such as fluorine, chlorine and bromine, especially chlorine and bromine;
Phenyl, biphenyl, naphthyl or pyridyl, where these aromatic radicals can carry one to five halogen atoms as mentioned under R¹, in particular chlorine and bromine and / or one to three of the following substituents:
Alkyl as mentioned above, especially methyl,
Haloalkyl as mentioned above, in particular trifluoromethyl and difluoromethyl,
Alkoxy as mentioned above, in particular methoxy,
Haloalkoxy as mentioned above, in particular trifluoromethoxy,
Phenoxy, phenylsulfonyl, amino, nitro, alkylamino such as methylamino, ethylamino, propylamino, 1-methylethylamino, butylamino, 1-methylpropylamino, 2-methylpropylamino and 1,1-dimethylethylamino, in particular nitro and amino and / or
Dialkylamino such as dimethylamino, diethylamino, dipropylamino, di- (1-methylethyl) amino, dibutylamino, di- (1-methylpropyl) amino, di- (2-methylpropyl) amino and di- (1,1-dimethylethyl) amino, especially dimethylamino,
R³ in general and in particular the radicals mentioned under R² and
X nitrogen or a methine group CH.

The Azolylmethyloxirane I or the growth regulators containing them Agents can be, for example, in the form of directly sprayable solutions, Powders, suspensions, also high-proof aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, Pastes, dusts, sprinkles or granules by spraying, Misting, dusting, scattering, brushing or pouring applied will. Seed treatments are also included in growth-regulating agents possible. The application forms depend on the purposes; they should in any case be the finest possible distribution of the invention Ensure active ingredients.

The compounds are generally suitable for the production of directly sprayable Solutions, emulsions, pastes or oil dispersions. As a formulation aid come mineral oil fractions from medium to high Boiling point, such as kerosene or diesel oil, as well as coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic Hydrocarbons, e.g. B. toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, Propanol, butanol, cyclohexanol, cyclohexanone, chlorobenzene, isophorone or strongly polar solvents, such as N, N-dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone or water.

Aqueous use forms can be made from emulsion concentrates, dispersions, Pastes, wettable powders or water-dispersible granules by adding be prepared by water. For the production of emulsions, pastes or oil dispersions, the substrates as such or in an oil or Solvent dissolved, using wetting agents, adhesives, dispersants or emulsifiers be homogenized in water. But it can also be more effective Substance, wetting, adhesive, dispersing or emulsifying agent and possibly solvent or oil existing concentrates are produced which are used for Dilution with water are suitable.  

The alkali, alkaline earth, ammonium salts come as surface-active substances of aromatic sulfonic acids, e.g. B. lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, as well as fatty acids, alkyl and alkylarylsulfonates, Alkyl, lauryl ether and fatty alcohol sulfates, and salts sulfated hexa-, hepta- and octadecanols, as well as fatty alcohol glycol ether, Condensation products of sulfonated naphthalene and its Derivatives with formaldehyde, condensation products of naphthalene or Naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or nonylphenol, alkylphenol, Tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, Fatty alcohol ethylene oxide condensates, ethoxylated castor oil, Polyoxyethylene alkyl ether or polyoxypropylene, lauryl alcohol polyglycol ether acetate, Sorbitol esters, lignin sulfite liquors or methyl cellulose into consideration.

The formulations contain between 0.1 and 95% by weight, preferably between 0.5 and 90 wt .-%, active ingredient.

The growth regulating active ingredients can, for example, as follows be formulated. The active ingredients are in a purity of 95 prepared up to 100% (NMR purity).

• I. 90 parts by weight of compound no. 109 are mixed with 10 parts by weight N-methyl-α-pyrrolidone and receives a solution that is suitable for use in the form of tiny drops.
• II. 20 parts by weight of compound no. 117 are in a mixture solved that from 80 parts by weight of xylene, 10 parts by weight of Addition product of 8 to 10 moles of ethylene oxide with 1 mole of oleic acid N-monoethanolamide, 5 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 5 parts by weight of the adduct of 40 moles of ethylene oxide to 1 mole of castor oil. By Pour out and finely distribute the solution in 100,000 parts by weight Water, an aqueous dispersion is obtained which contains 0.02% by weight contains the active substance.
• III. 20 parts by weight of compound No. 115 are mixed solved that from 40 parts by weight of cyclohexanone, 30 parts by weight Isobutanol, 20 parts by weight of the adduct of 7 moles of ethylene oxide with 1 mole of isooctylphenol and 10 parts by weight of the adduct of 40 moles of ethylene oxide with 1 mole of castor oil consists. By pouring in and finely distributing the solution an aqueous dispersion is obtained in 100,000 parts by weight of water, which contains 0.02% by weight of the active ingredient.  
• IV. 20 parts by weight of active ingredient No. 109 are mixed solved that from 25 parts by weight of cyclohexanone, 65 parts by weight a mineral oil fraction with a boiling point of 210 to 280 ° C and 10 parts by weight of the adduct of 40 moles of ethylene oxide of 1 mole of castor oil. By pouring and fine The solution is distributed in 100,000 parts by weight of water an aqueous dispersion containing 0.02% by weight of the active ingredient.
• V. 20 parts by weight of active ingredient No. 110 with 3 parts by weight the sodium salt of diisobutylnaphthalene-α-sulfonic acid, 17 parts by weight of the sodium salt of a lignosulfonic acid a sulfite waste liquor and 60 parts by weight of powdered silica gel well mixed and ground in a hammer mill. By finely distributing the mixture in 20,000 parts by weight Water gives a spray mixture which contains 0.1% by weight of the active ingredient contains.
• VI. 3 parts by weight of active ingredient no. 112 become 97 parts by weight finely divided kaolin mixed. You get this way a dust containing 3% by weight of the active ingredient.
• VII. 30 parts by weight of active ingredient No. 117 are mixed 92 parts by weight of powdered silica gel and 8 parts by weight Paraffin oil that is on the surface of this silica gel was sprayed, mixed intimately. You get on this Wise preparation of the active ingredient with good adhesiveness.
• VIII. 20 parts by weight of active ingredient No. 116 are mixed with 2 parts by weight Calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight Fatty alcohol polyglycol ether, 2 parts by weight of sodium salt one Phenol-urea-formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil intimately mixed. You get one stable oily dispersion.
• IX. 40 parts by weight of compound No. 109 with 10 parts Sodium salt of a phenolsulfonic acid-urea-formaldehyde Condensate, 2 parts silica gel and 48 parts water intimately mixed. A stable aqueous dispersion is obtained. By diluting with 100,000 parts by weight of water, an aqueous is obtained Dispersion containing 0.04% by weight of active ingredient.

Powders, materials for spreading and dusts can be mixed or combined Grinding the active substances with a solid carrier will.  

Granules, e.g. B. coating, impregnation and homogeneous granules by binding the active ingredients to solid carriers. Solid carriers are mineral soils such as silicas, silica gels, silicates, Talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, Diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground Plastics, fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, Urea and vegetable products, such as flour, tree bark, Wood and nutshell flour, cellulose powder or other solid Carriers.

The formulations or the ready-to-use preparations made from them such as solutions, emulsions, suspensions, powders, dusts, pastes and granules are made in a known manner, for example in the pre-emergence process or applied post-emergence or used as a mordant.

The azolylmethyloxiranes of the general formula I can be practically all Different stages of development of a plant are affected therefore also used as growth regulators. The variety of effects of Connections depend on various factors. The decisive factors are especially

• a) plant type and variety,
• b) time of application, with regard to the development stage of Plant and season,
• c) Application site and method (seed dressing, soil treatment or Leaf application)
• d) climatic factors, e.g. B. temperature, rainfall, also also day length and light intensity,
• e) soil conditions (including fertilization),
• f) formulation or use form of the active ingredient and
• g) application rate and active substance content of the agents.

From the series of different possible uses of the invention Plant growth regulators in crop cultivation, in agriculture and in horticulture, some examples are listed below:  

• A. With the growth-regulating azolylmethyloxiranes I, the vegetative growth of the plants can be strongly inhibited, which manifests itself in particular in a reduction in the growth in length. The treated plants accordingly have a compact stature; a darker leaf coloration can also be observed.
  As an advantage in practice, z. B. the reduction of grass cover on roadsides, hedges, canal embankments and on lawns such as parks, sports and orchards, ornamental lawns and airfields, so that the labor and costly grass clippings can be reduced.
  In the case of fruit trees and other trees or shrubs, costly cutting measures can be reduced.
  It is also of economic interest to increase the stability of crops that are susceptible to storage, such as cereals, rice, corn, sunflowers and soybeans. The resulting shortening and strengthening of the straw reduce or eliminate the risk of "storing" (twisting) of plants under unfavorable weather conditions before harvesting.
  It is also important to use it to inhibit the growth in length and to change the maturity of cotton over time. This enables fully mechanized harvesting of these important crops.
  By using the compounds I, the lateral branching of the plants can also be increased or inhibited. There is interest if, for. B. in tobacco plants the formation of side shoots (stinging shoots) should be inhibited in favor of leaf growth.
  With the compounds I, for example in winter rape, the frost resistance can also be increased considerably. On the one hand, the growth in length and the development of a lush (and therefore particularly susceptible to frost) leaf or plant mass are inhibited. On the other hand, the young rapeseed plants are retained in the vegetative development stage after sowing and before the onset of winter frosts, despite favorable growth conditions. This also eliminates the risk of frost for plants that tend to prematurely degrade flowering and switch to the generative phase. Also with other cultures, e.g. B. Winter cereals, it is advantageous if the stocks are well stocked by treatment with compounds according to the invention in autumn, but do not go into the winter too abundantly. This can prevent increased sensitivity to frost and - due to the relatively low leaf or plant mass - infestation with various diseases (e.g. fungal disease). The inhibition of vegetative growth also enables denser planting of the soil in many crop plants, so that an additional yield, based on the soil area, can be achieved.
• B. With the growth-regulating agents based on azolylmethyloxiranes I, additional yields can be achieved both on parts of plants and on plant constituents. For example, it is possible to induce the growth of larger quantities of buds, flowers, leaves, fruits, seeds, roots and tubers, to increase the sugar content in sugar beets, sugar cane and citrus fruits, to increase the protein content in cereals or soybeans or to grow rubber trees to stimulate the increased latex flow.
  The azolylmethyloxiranes of the formula I can cause increases in yield by interfering with the plant metabolism or by promoting or inhibiting vegetative and / or generative growth.
• C. With azolylmethyloxiranes I, both a shortening or lengthening of the development stages and an acceleration or deceleration of the ripeness of the harvested plant parts can be achieved before or after the harvest.
  Ease of harvest, for example, is of economic interest, which is made possible by the time-related falling or decreasing of the adhesive strength on the tree in the case of citrus fruits, olives or other types and varieties of pome, stone and nuts. The promotion of the formation of a separating tissue between the leaf and shoot axis is also for a well controlled defoliation of crops such. B. Cotton essential.
• D. The azolylmethyloxiranes I can further reduce the water consumption of plants. This is particularly important for agricultural land that has to be artificially irrigated at a high cost, e.g. B. in arid or semi-arid areas. By using the substances according to the invention, the intensity of the irrigation can be reduced and thus more economical management can be carried out. Under the influence of growth regulators there is a better use of the water available because, among other things
  • - The opening width of the stomata is reduced
  • - A thicker epidermis and cuticle are formed
  • - The root penetration of the soil is improved
  • - The microclimate in the crop is favorably influenced by a more compact growth.

The active compounds to be used according to the invention can be used in crop plants both from the Samer (as a seed dressing) and from the soil, d. H. through the root and by spraying over the leaf.

Due to the high tolerance of the plants for the compounds I can the application rate can be varied widely. When treating seeds generally amounts of active ingredient from 0.001 to 50 g per kilogram of seed, preferably 0.01 to 1 g. For leaf and soil treatment are generally applications from 0.01 to 10 kg / ha, preferably 0.1 to 5 kg / ha sufficient.

To broaden the spectrum of activity and to achieve synergistic The growth-regulating azolylmethyloxiranes I can also have effects numerous representatives of other herbicides or growth regulators Active ingredient groups are mixed and applied together. For example come as mixing partners diazines, 4H-3,1-benzoxazine derivatives, benzothiadiazinones, 2,6-dinitroanilines, N-phenyl carbamates, thiol carbamates, halocarboxylic acids, Triazines, amides, ureas, diphenyl ethers, triazinones, uraciles, Benzofuran derivatives, cyclohexane-1,3-dione derivatives, quinolinecarboxylic acid derivatives, Phenyloxy- or heteroaryloxy-phenylpropionic acids as well their salts, esters and amides and others into consideration.

It may also be useful to use the compounds of formula I alone or in combination with other herbicides or growth regulators to be mixed with other crop protection products, for example with pest control or phytopathogenic agents Fungi or bacteria. Miscibility is also of interest with mineral salt solutions, which are used to correct nutritional and Trace element deficiencies are used. It can also be nonphytotoxic Oils and oil concentrates can be added.

The rules set out in the synthesis examples below were obtained with appropriate modification of the starting compounds  further compounds of formula I used; the connections obtained are in the following tables with physical information listed.

I. Production of the starting materials Regulation 1 E / Z-2- (4-fluorophenyl) -3- (2-chlorophenyl) propenal

To a solution of 35 g of 2-chlorobenzaldehyde in 300 ml of methanol Pour 4.2 g of sodium hydroxide into 30 ml of water. The reaction mixture is cooled to 10 ° C. and 36 g of 4-fluorophenylacetaldehyde are quickly added, the temperature in the solution rising to 30-40 ° C. To The crystals which have precipitated out are stirred for 10 hours at 40 ° C. sucked off the cooled reaction solution.

Regulation 2 cis-2-formyl-2- (4-fluorophenyl) -3- (2-chlorophenyl) oxirane

78.2 g of E-2- (4-fluorophenyl) -3- (2-chlorophenyl) propenal are dissolved in 300 ml Dissolved methanol and 1 ml of sodium hydroxide solution (conc.) Added. The reaction solution is stirred at 0 ° C, while 20.5 g of hydrogen peroxide (approx. 50%) be slowly added dropwise, the internal temperature of 30 ° C. is not exceeded. After the addition has ended, the mixture is stirred for six hours Stirred at room temperature, then added 100 ml of water and the The resulting emulsion is shaken out with methyl tert-butyl ether. The The isolated organic phase is then dried over sodium sulfate and constricted. 52.5 g (63%) of cis-2-formyl-2- (4-fluorophenyl) -3- are obtained. (2-chlorophenyl) oxirane.

II. Production of the end products Example 1

To a solution of 29.7 g of triazole in 150 ml of methylene chloride 0 ° C under a nitrogen atmosphere 12.8 g of thionyl chloride. To completed addition is stirred at room temperature for 30 minutes and then 20 g of cis-2-formyl-2- (4-fluorophenyl) -3- (2-chlorophenyl) - added oxirane. After the reaction mixture at 12-15 hours Stirring room temperature, 100 ml of water is added to the solution and the separated organic phase. The remaining aqueous phase becomes Shaken twice with methylene chloride and the collected organic  Phases twice with saturated sodium bicarbonate solution washed. The isolated organic phase is then over sodium sulfate dried and concentrated to give 23.7 g (85%) cis-2- [1- (1,2,4- Triazol-1-yl) -1-chloromethyl] -2- (4-fluorophenyl) -3- (2-chlorophenyl) ox-iran be obtained as a 2: 1 mixture of diastereomers. You get out Methyl tert-butyl ether 5.8 g of the increasingly formed diastereomer A with a melting point of 152-156 ° C (compound no. 108).

Example 2

To a solution of 14.9 g of triazole in 75 ml of methylene chloride 11.2 g of thionyl bromide were added at 0 ° C. under a nitrogen atmosphere. To completed addition is stirred at room temperature for 30 minutes and then 10 g of cis-2-formyl-2- (4-fluorophenyl) -3- (2-chlorophenyl) - added oxirane. After the reaction mixture at 12-15 hours Stirring room temperature, 100 ml of water is added to the solution and the separated organic phase. The remaining aqueous phase becomes Shaken twice with methylene chloride and the collected organic Phases twice with saturated sodium bicarbonate solution washed. The isolated organic phase is then over sodium sulfate dried and concentrated, whereby 10.5 g (72%) cis-2- [1- (1,2,4- triazol-1-yl) -1-bromomethyl] -2- (4-fluorophenyl) -3- (2-chlorophenyl) oxy-ran be obtained as a 2: 1 mixture of diastereomers. You get out Methyl tert-butyl ether 3.5 g of the increasingly formed diastereomer A with melting point 151-155 ° C (compound no. 110).  

Active substances table

Examples of use

The growth-regulating effect of the azolylmethyloxiranes of the formula I. was shown by greenhouse experiments:

Plastic flower pots with a content of 500 cm³ were used to grow the test plants and sufficient nutrient-rich culture substrate. The seeds of the Test plants were sown flat according to species.

With pre-emergence treatment, the processed active ingredients became immediate then applied to the earth's surface. They were here in water as Distribution medium suspended or emulsified and by means of finely distributing Sprayed nozzles. After the agents were applied, the vessels became light watered to get germination and growth going. After that, the Vessels covered with clear plastic hoods until the plants have grown were. This cover promotes even germination of the test plants.

For the purpose of post-emergence treatment, the test plants were Growth habit first grown to a height of 3 to 15 cm and only then then with the active ingredients suspended or emulsified in water treated. The test plants were either sown directly and in the same vessels or they were first separated as seedlings bred and into the test tubes a few days before treatment transplanted. There was no coverage during post-emergence treatment.

The test vessels were set up in the greenhouse, whereby for heat-loving Species warmer areas (20 to 35 ° C) and for those more moderate Climates of 10 to 25 ° C were preferred.

The observed growth-regulating effect was repeated at the end of the test about 14 days by height measurement. The measured values obtained in this way were related to the height of the untreated plants.

The color intensity increased in line with the reduction in length growth of leaves on. The increased chlorophyll content also leaves an increased level Expect photosynthesis rate and thus an increased yield formation.

The growth-regulating effect of Azolylmethyloxirane I is the the following tables. As a well-known growth regulator Chlormequat chloride (CCC) tested in parallel with the azolylmethyloxiranes.  

Table 1

Influencing the growth in length of summer rape "Petranova" in post-emergence leaf treatment

Table 2

Influencing the length growth of soybeans "Maple Arrow" in post-emergence leaf treatment

Those in the greenhouse experiments for those shown in Tables 1 and 2 Plants used in tests are composed of the following types:

Wheat (Tritieum), Barley (Hordeum vulgare), Rice (Oryza sativa), Sunflower (Helanthus annus), oilseed rape (Brassia napus) and soybean (Glycine Max.).

Claims (3)

1. Plant growth regulating agents containing azolylmethyloxiranes of the general formula I in which the substituents have the following meaning:
R¹ is a halogen atom,
R², R³ C₁-C₈-alkyl, which can carry one of the following radicals: dioxanyl or phenyl, where the phenyl radical in turn can carry one to five halogen atoms and / or one to three of the following groups: C₁-C₄-alkyl, C₁-C₄ -Haloalkyl, C₁-C₄-alkoxy and / or C₁-C₄-haloalkoxy,
C₃-C₈-cycloalkyl, C₅-C₈-cycloalkenyl, tetrahydropyranyl or norbornyl, where these cyclic radicals can carry one to three of the following substituents: C₁-C₄-alkyl and / or halogen,
Phenyl, biphenyl, naphthyl or pyridyl, where these aromatic radicals can carry one to five halogen atoms and / or one to three of the following substituents: C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄- Haloalkoxy, phenoxy, phenylsulfonyl, amino, C₁-C₄-alkylamino, di-C₁-C₄-alkylamino and / or nitro,
X nitrogen or a methine group CH
or their environmentally compatible salts and other inert additives. 2. Use of azolylmethyloxiranes of the general formula I according to Claim 1 as a plant growth regulator. 3. Process for regulating plant growth, characterized in that that a regulatively effective amount of an azolylmethyloxirane of the formula I on the seeds, the plants and / or their Living space.