SE425246B - TRIAZOLD DERIVATIVES WITH FUNGICIDE, BACTERICIDE OR EXTRACTIVE USE - Google Patents

Description

10 15 20 25 50 7512643-5 2 such as N, N-dimethylformamide, N, N-dimethylacetamide, aceto- solvent, Such solvents can be used nitrile, benzonitrile or the like. in combination with other reaction-inert organic solvents, dimethylbenzene or the like. When Y bromine or chlorine, it is advisable to add an alkali metal talliodide, e.g. sodium or potassium iodide. Slightly elevated tempe- temperatures increase the reaction rate and preferably the reaction is carried out at the reflux temperature of the reaction mixture.

The ketal formed of formula (I) is then isolated from the reaction medium. possibly such as benzene, methylbenzene, mixture by conventional methods and purified purification procedure, for example by further according to any custom trituration, chromatography, etc. crystallization, extraction, The specified procedure can be further illustrated by the following way: N _ I-cnï- ø-Ar 1 '' o \ o (III) N \ Naome \ / H>> (II) DNF, NaI (I) The compounds of formula (I) thus obtained, in basic form, can be transferred to therapeutically useful acid addition salts by reaction with a suitable acid, such as an inorganic acid, such as as a hydrogen halide, ie hydrogen chloride, hydrogen bromide or hydrogen iodide, nitric acid or thiocyanic acid, a phosphoric acid, an organic hydroxyacetic acid, sulfuric acid, acid, such as acetic acid, propionic acid, oxypropionic acid, 2-oxopropionic acid, oxalic acid, malonic acid, succinic acid acid, maleic acid, fumaric acid, 2-hydroxy-succinic acid, 2,3-dihydroxy- succinic acid, 2-hydroxy-1,2,3-propanetricarboxylic acid, benzoic acid, 5-phenylpropionic acid, Rehydroxybenzeneacetic acid, methanesulfonic acid, ethane sulfonic acid, hydroxyethanesulfonic acid, H-methylbenzenesulfonic acid, 6k-hydro- oxybenzoic acid, H-amino-2-hydroxybenzoic acid, 2-phenoxybenzoic acid or The salts are in turn transferred to the corresponding by reaction with alkali, so- 2-acetyloxybenzoic acid. the free bases in the usual way, e.g. as sodium or potassium hydroxide. The starting materials of formula (III), some of which are known compounds, can be prepared according to known methods. Such wherein Z represents a group -CH 2 -CH 2 -, -CH (CH 3) -CH 2 -, -CH (CH3) -CH (CH3) - And -CH2-CH2-CH2- and methods of preparation of these compounds are described in U.S. Pat. No. 3,575,999 10 15 25 30 7512643-3 3 _ The compounds of formula (III) are prepared EGHOW that a suitable Ke ' ton of formula (IV), wherein Ar and Y have the meanings given, with a suitable diol of formula (V) according to known ketalization methods, which are described in the literature (see eg Synthesis, 197Ä '(l), 23).

According to a preferred method, the two reactants are refluxed together for several hours, azeotropically removing water in a suitable organic solvent, preferably in the presence of a simple alcohol, such as ethanol, propanol, butanol, pethanol or the like and in the presence of a suitably strong acid, such as U-methylbenzene " sulfonic acid. Suitable organic solvents, which can be used for for this purpose, for example, aromatic hydrocarbons such as benzene, methyl benzene, dimethylbenzene and the like, and saturated hydrocarbons such as cyclohexane. 8 Ar-C-CH2Y + H0-Z-OH U-methylbenzenesulfonic acid algae (III) butanoï / ' (IV) (V) benzene The ketones of formula (IV) are known and can be prepared according to methods known to those skilled in the art. IN From formula (I) it appears that several of the compounds according to The present invention has asymmetric carbon atoms in the structure and consequently, they may exist under different stereochemical, optical isomer forms. When an alkyl group is present in the ü position of the dioxolane nucleus, is the carbon atom to which the alkyl group is attached, and the carbon but in the 2-position of the dioxolane nucleus asymmetric. The stereochemicals and the optical isomers of the compounds of formula (I) may be separated and isolated according to methods known to those skilled in the art. The specified iso- the merits fall within the scope of the invention.

The compounds of formula (I) and the acid addition salts thereof are useful agents in the control of fungi and bacteria. Before- the compounds of the invention are valuable in the treatment of plants, animals and humans, infested with pathogenic micro - organisms, and for the destruction of microorganisms on materials.

The compounds of the invention are very strong fungicides, which can be used in agriculture. They are very active towards one large number of fungi, e.g. against the fungi, which are responsible for the emergence of apple powdery mildew on various plants, against Erysiphe graminis, Erysiphe polygoni, Erys fi km cichoracearum, Erysiphe polyphaga, Podosphaera leuchotricha, Sphaerotheca pannosa, Sphaerotheca mors-uvae, Uncinula 10 15 20 25 50 7512643-3 necator, etc, and other fungi, e.g. Venturia inaequalis, C0l1et0 * trichum lindemuthíanum, Fusarium oxysporum, Alternaría tenius, Thielaviopsis basicola, Helminthosporium gramineum, Penicillium degítatum, etc.

They are especially useful because of their PP ° fy1akti $ ka lik ' as a threatening and systemic effect. Their strong action against phyto- pathogenic fungi are more clearly illustrated by the results obtained in the following experiments. e In several of these experiments the compound 1- (2- (2, "" diK10P ') was used phenyl) -1,3-dioxolan-2-ylmethyl-1H-1,2, "' representative type of the compounds of formula (I). , __ N H I NW) a i ¿“2? ° \ ï @ '° * L___J (I-a) The compounds for which experimental results are given have not been given to limit the invention to these compounds but only for to exemplify the strong antifungal activity of all compounds within the scope of formula (I). _ A. Prophylactic action of compounds of formula (I) against Erysiphe cichoracearum on cucumber during leaf treatment.

Young cucumber plants, about 10 days old, were sprayed with a water- solution containing 250, 100 or 10 ppm of the compound which were to be examined, while the comparison plants were untreated. Then the plants had dried, they were artificially infected with spores of Erysiphe cichoracearum by rubbing heavily infected leaves against the plants. The 15th day after the artificial infection the degree of fungal infestation is evaluated by counting the number spots per plant. The results given in Table I are average it for two plants and are expressed according to the following scoring system. '0 = 0 spots per plant 1-5 spots per plant 6-10 spots per plant more than 10 spots per plant 1 2 3 5 1512643-3 Table I Prophylactic action of compounds (I) against Erysiphe cichoracearum on cucumber plants during leaf treatment è fl a Ar 0 0 R Bass- Effect against fungus, ”Ü Ar R or noäng v salt form 250 npm 100 npm 10 pmm 2,4- (Cl) Z-C6H3 H base - 0 0 661-15 H bass - 3 - 4-NO2-C6H4 H base 0 .- .. 3-C1-C6H4 H base - 2 - 2-Cl-Cßlï4 H (COOI-Uz - 0 _ 4-Br-C6EI4 H base 0 - - 2-Br-C6H4 H (COOH) ¿- 2 .. a-ocna-c 6:14 H (cool-na 1 - _ z-cH3-c6H4 H (coomz o _ _ 4-F-C6H4 H (COOIZZ 0 - _ 4-CH3-C6H4 H (COOI-Uz 0 - - 4-C1-C6H4 H (COOH) 2.H2O - O - Z-naphthyl H (COOI-OZ 0 - - 2, 5- (Cl) 2-C6H3 H (COOEUZ - 0 - 4-cN-c6H4 H (coomz o - _ ß, 4- (c1) ¿-c6H3 H (coomz - 3 _ 2-0CH3-C6H4 H (COOI-I2 I - - Z-thienyl H (COOH) 2 - 2 - 2 -fl uo renyl H bas 0 - ~ S-Cl-Z -thienyl H base - Z - á _ / 1 _: - 7512643-3 6 .Table I, cont .; Bas- Effect against fungus, Is R or noäng sal fi form zsonpm loonnm 10 »UM 3-Br, 4-CH 3 -C 6 H 3 H base 0 - - z-CHSA-Br-cone H A base - z - -Z-CHB, 4-C1-C6H3 H base 0 - - 3-Br-C6H4 H base 2 - - 4-I-C¿H4 H (COOI-Uz 0 - - 3, S- (CUZ-COL-IS H (COOH) 2 - 2 - z, s- (cnz-cóH3 H (coomz o _ - 3-NO2-C6H4. H base 1 - - z, 4- (Br) 2-c6H3 H (coomz - 1 _ 2, 4, 5- (C1) 3-C6_H2 H (COOI-Dz 0 - - Z-Cl. 4-OCH3-C6H3 H (COOI-Uz - 2 - _2,4- (C1) z-C6H3 CH3 HNO? 0 - - 2,4- (C1) 2-C6H3 C2HS I-INO3 - 0 0 z, 4- (602-061-13 1103: 17 HNo3 - o o g, 4- (Cl) ¿-C6H3 nC4H9 l1 / 2 (COOH) 2 - Z - 2-, 4- (Cl) ¿-C6H3 nCsH1-1 HNO3 - 0 D 2. 4- (C1) 2-C6H3 nCoHl 3 l-INOB 0 - - 2,4 (C1) 2-C6H3 nC7I-I15 HNOS - 2 - 2, ßta- (CDZ-CGHS nCal-Il 7 HNO3 0 - - 10 7 7512643-3 A.l Prophylactic action against Erysíphe polyphaga on cucumber in leaf treatment.

Young cucumber plants in the one-leaf stage were sprayed with a water- containing solution, containing 500, 250 or 125 ppm of (I-a), while the comparison plants were untreated. An artificial infection with spores of Erysiphe polyphaga were carried out by rubbing strongly infected leaves against the plants on the 4th, 6th or 8th day after On the 18th and 3rd day after treatment, the proportion of leaf surfaces that were attacked by the fungus separately for affected leaves and for newly formed leaves. The results given in bell I.l are averages for 5 plants and expressed as a percentage of the treatment. grip in comparison with the untreated plants.

Table I.l Prophylactic action of (I-a) against Erysípe polyphaga on cucumber during leaf treatment Evaluation- 18 days BN days day after treatment after treatment Infected on 1 specified day eft. 4 6 3 4 6 3 2 the treatment '' Infected leaf (a) or. 5 Ilšçldade blad a b a b a b a b a b a b Concentration of (I-a) and spray- solution untreated 1oo 1oo 1oo zoo 1oo 1oo 1oo xoo 1oo 1oo 160 100; 500 ppm å 250 ppm o o o o o o o o o n o 3 l IN 125 Ppm o o o .o o o o o o o o o , '7512643-5 8 Prophylactic action against Erysiphe graminis on grains in soil treatment.

Barley plants were treated by irrigating each plant with 100 ml of an aqueous solution containing 1000, 100 or Δ 10 ppm (I-a). Comparison plants received the same volume of solution, as however, did not contain (I-a). The natural infection, which is usually hits, when the plants are kept in greenhouses near infected plants, was evaluated 16 days after treatment by counting the number of spots on the leaves. 5 plants were used per experimental series And the results in Table II are averages, which are expressed in f central attack in relation to the comparison plants.

Table II Prophylactic action of (I-a) against Erysiphe graminis on grains during soil treatment Dose in mg (I-a) Attack in% in proportion per plant to comparison plant Comparison Plant 100 100 mg 0 10 mg o 1 must 53 C. Healing effect against Erysiphe graminis on barley at leaf treatment.

Barley plants, which were attacked by Erysiphe graminis, were sprayed With an aqueous solution containing (I-a) in the indicated concentration ration. On the 16th day after treatment, the number was determined spots per plant. 5 plants per experimental series were used and the results, given in Table III, are averages, which are expressed in percentage infestation in relation to the comparison plants. 0 Table III Healing effect of (I ~ a) against Erysiphe graminis on grains in leaf treatment Concentration of (I-a) Attacks in% in in the spray solution is comparable to nlantor O 100 1000 ppm 0 100 ppm ~ 1.5 10 ppm 25 I h: V-.v-mv-mvru-.zarn ..v ... «_...,» -_, _. -aßw '.r an »_ - -» - -_ - \ --- -fl 10 15 20 9 '7512643-3 D. Prophylactic action of (I-a) against Podospaera leuchotricha on dilute apple seedlings when spraying.

One-year-old apple seedlings were sprayed with an aqueous solution. containing (I-a) in the indicated concentration. The plants are infectious artificially as described in Sample "A" with spores of Podosphaera leuchotricha 1 day after treatment and incubated for 36 hours. The degree of fungal infestation was evaluated 25 days after the action by counting the number of spots. Two plants per experimental series were used and the results given in Table IV are averages, which are expressed in percentage attack in relation to the comparison plants.

Table IV Prophylactic action of (I-a) against Podosphaera leucotricha on dilute apple seedlings when sprayed Attack in% in relation to comparison plants Concentration of (I-a) in the spray solution O 100 100 ppm 0 10 ppm 6 E. Action against Thielaviopsis sp. 5 mm thick slices of potato and leek were dipped in a water- containing sample solution, which contained (I-a) in the indicated concentrations.

The dips were placed after dipping on filter paper on a large plastic tray and the tray was covered with glass. An artificial infectious was performed on the day of treatment by spraying the discs with a concentrated suspension of spores of Thielaviopsis sp. and the discs were incubated at room temperature.

Fungal growth on the discs is evaluated 6 days after treatment. by estimating the fungal infestations on the surface. The results data given in Table V are expressed as a percentage of the holding to the comparison plants.

Table V Effect of (I-a) against Thielaviopsis sp.

Concentration of (I-a) Attacks in% in relation in the sample solution in ppm to the comparator lantern Potato Leek 0 100 100 1000 0 100 0 0 10 or 142.8 1 ll 100 10 15 20 25 . »-.« ...-.........__, ._, - 751126 43-5 10 The compounds of formula (I) are also very active against one large number of fungi, which are pathogenic to humans and animals. They are for example, active against fungi such as Hicrosporum canis, Trichophyton 'mentagrophytes, Trichophyton rubrum, Aspcrgillus fumigatus, Phialo- phora verucosa, Cryptococcus neoformans, Candida albicans, Candide tropicalis, etc. The extraordinary beneficial effect against Candida albicans is clearer from the results obtained in the following experiments.

F. Effect of (I-a) on Candida infestation on the demand of turkeys.

Young turkeys (lü days old) were artificially infected by that the requirement was forcibly added to a suspension containing U.10 C.F.U. (colony forming units) of Candida albicans.

When the animals became infected, they either received their normal diet ( group), or a medicated feed, which contained 125 ppm off (I-a). Two weeks later all the turkeys were killed, cultures were made by the requirement and the number of Candide colonies per gram require was calculated.

The results are summarized in Table VI.

Table VI ' Number of colonies of Candida albicans per gram required in the turkeys treated with (I-a) - (125 ppm) or placebo.

Treatment Number of animals Number of Candida colonies gper grams require Comparison - 3,520,000 animal 2 sus 700 3 3 132 000 H 1 909 000 (I ~ a) 1- 0 (125 ppm) 2 2117 zoo 3 6 7ü2 As can be seen from the results in Table VI, the compound (I-a) in a concentration of 125 ppm particularly effective against attack on the requirement in relation to the corresponding untreated animals.

G. Effect of (I-a) on vaginal Candide attacks on rats In female rats weighing 100 g, eggs were removed the logs and the uterus. About 3 weeks later, all animals were given a weak subcutaneous injection of 100 mg estradiolundecylate and the was injected intravaginally with a suspension containing 8,105 C.F.U. 10 15 20 11 _ _ 7512643-3 of Candida albicans.

Groups of Ä rats were then treated orally in l fl after each other. the following days with either a solvent (PEG 200) or (I-a). The administered dose of the compound was HO mg / kg orally. Vaginal samples were taken from all animals at the end of treatment. (ie lay days), and these were grown on Sabouraud agar medium, which contained penicillin (20 I.U./ml) and Streptomycin UH (pg / ml) and the number of Candida colonies were then counted.

Table VII summarizes the results obtained with (I-a) against vaginal Candide attacks in rats.

Table VII Number of animals per cultural assessment Treatment Number of Day after Culture Assessment X) animal treatment O l 2 3 Comparison (Pm zoo) u 1 "° Û ° 1 3 (I-a) (40 mg / kg 4 lä 3 1 O 0 0 orally) - X) Culture assessment: 0 no plant l-25 colonies 26-100 colonies_ > 100 colonies countless colonies As can be seen from the results in Table VII, (I-a) is a lot effective against vaginal Candida infestation in rats.

H. Effect of (I-a) on systemic Candida attacks on guinea pigs.

Male adult guinea pigs were infected intravenously with Candida -kulwl-I u I! u n n albicans, which causes a general systemic candidiasis.

Subsequently, 7 guinea pigs were treated orally in shelter one after the other days with either solvent (PEG 200) or (I-a). The the dose used was 30 mg / kg body weight.

Four days after the last day of treatment, everyone was killed the animals, the kidneys were removed and grown on Sabouraud agar medium, containing penicillin (20 I.U./ml) and Streptomycin (fl üfug / ml) and the number of isolated colonies of Candide albicans per gram of kidney Table VIII shows the detailed results obtained with (I-a) against systemic deep mycosity in guinea pigs. was counted. 1 l 10 15 20 25 7512643-3 12 Table vIII Number of Candida colonies Treatment Number animals per gram of kidney Comparisons l 182 (PEG 200) 2 2858 } 25220 1! - 385 5 19800 6 113 7 345 (I-a) 1 0 (H0 mg / kg 2 18 (orally) 3 0 H Of S 0 6 53 7 0 From the results in Table VIII it can be concluded that (I-a) is an extremely potent agent against systemic deep mycosity in guinea pigs.

The compounds of formula (I) have, apart from the antimicrobial bial effects, valuable plant-regulating properties. Dependent on various factors, such as the nature of the plants under treatment and dose of the added active ingredient, it may be observed the effect is either growth-stimulating or growth-inhibiting The present compounds as such are useful as such In particular, they may edge. applies to regulating the growth of plants. used as plant inhibitors or as plant retarders, especially as inhibitors of root growth, e.g. on tobacco plantor. In certain circumstances, however, they may also be used pdas as growth stimulants for plants.

The plant regulating properties of the compounds of formula (I), which are, of course, intended to fall within the scope of present invention, is more clearly illustrated by the results obtained in the following experiments, in which the compound (I-a) was used as a rep representative of the compounds of the invention. The results obtained complied with (I-a), are not intended to limit the invention but to only to exemplify the useful plant regulating properties of all compounds within the scope of formula (I).

- I. Plant-regulating effect on tomato plants during soil treatment.

Young tomato plants, which were 5.5 to U if tall, were planted in separate pots. Each pot was watered with a sample solution, which . ~ - _ .. ... vu-ra u '.'.... = ..-_'.._. _4I - '. T *? ...' - V 10 15 20 Ü 7512643 ”3 contained the specified amount of (I-a). The plant was evaluated by that the length and weight of the plants were determined 28 days later the treatment.

The results given in Table IX are averages of five plants and are expressed as a percentage in relation to the the plants.

Table IX Plant-regulating effect of (I-a) on tomato plants in soil treatment Dose of (I-a) Plant length in% Plant weight in% in mg / plant in relation to in relation to the comparison lanterns the comparison lanterns No 100 100 10 llü 118 l 127 134 0.1 122 116 J. Plant regulating effect on barley during leaf treatment.

Young barley seedlings in the 3-H leaf stage were sprayed with a sample solution. 'The effects on plant growth was evaluated 2U days after treatment by containing (I-a) of the indicated concentrations. that the weight of the plants was determined. The results, given in Table X, represent averages for 10 plants and are expressed as a percentage in to the comparison plants. .

Table X Plant regulating effect of (I-a) on barley during leaf treatment Conc. of (I-a) in the mean weight of the Plants the sample solution in% of the (nom) plants No 100 125 126 60 116 K. Impact of root shoot growth on tobacco plants.

Tobacco plants, var. "Xanthi", was pulled up in greenhouses and topped in early bud stage.

After 5 days, a foliar spray treatment was performed with an aqueous suspension of compound (I-a) in amounts corresponding to 3 and 1.5 kg a.i./ha. a Each treatment was repeated three times. 12 days after the plot, the plant was estimated by the root shoots in comparison with those topped and untreated comparison plants. 10 15 20 25 30 1512643-5 _11 ..

The recorded reductions in rhizome growth were 100% at 3.0 kg / ha and 90% at 1.5 kg / ha.

L. Plant inhibition on soybean plants.

Soybean plants, var. "Hark", was grown in pots in a growing chamber at 2300, 20,000 Lux and a day length of shelter hours. Deed third trifoliate leaf had developed, the plants were sprayed with a containing suspension of compound (I-a) in concentrations of 1000, 500, 100 and 50 ppm active ingredient.

The percentage of plant inhibition in the treated plants in relation to the comparison plants were determined after le days.

The following results were obtained: Treatment% plant inhibition (I-a) 1000 ppm a.í. 70% 500 ppm a.i. H0% 100 ppm a.i. 25% 50 ppm ani. 'oß Comparison plants 0% At the concentration of 1000 ppm, a more intense green could color of the foliage is observed.

Due to the stated fungicidal, antibacterial compounds of the compounds and plant regulating properties, according to the present invention prepare valuable compositions, which include the present the ketals (I) or acid addition salts thereof as the active ingredient the ingredient in a solvent or a solid, semi-solid or liquid the diluents or carrier materials. In addition, the invention includes an effective method for controlling fungal or bacterial growth using an effective bactericidal or fungicidal amount of such ketals (I) or salts thereof. The present compounds can be used in suitable solvents or diluents, in the form of emulsions, suspensions, dispersions or ointments, as appropriate solid or semi-solid carriers, in natural or synthetic soaps, detergents or dispersion media, optionally together with other compounds with arachnicides, insecticides, ovicides, fungicides cida and / or bactericidal properties'or together with inactive additives. Solid carriers suitable for the manufacture of compositions in powder form, include various inert, porous and powdered dispersants of inorganic or organic nature, 10 15 20 25 35 HO - 7512643-5 15 such as tricalcium phosphate, calcium carbonate, in the form of processed chalk or limestone, kaolin, tree trunks, bentonite, talc, diatomaceous earth or boric acid, which is ground; powdered cork, sawdust and other fine powder materials of vegetable origin can also be used as carrier substances.

The active ingredient is mixed with these carriers. for example by grinding them thereby; alternatively, the inert is impregnated the carrier substance with a solution of the active component in a volatile solvent and the solvent is then removed by heating or suction filtration at reduced pressure. By adding wetting agents and / or dispersants, such powder preparations may can also be easily wetted with water, so that suspensions are held.

The inert solvents used in the preparation of liquids preparations should not be flammable and should be so far may be odorless and non-toxic to warm-blooded animals or for plants in the surrounding environment. Solvents, as appropriate for this purpose, high-boiling oils, e.g. of vegetable origin and low-boiling solvents with a flash point of at least 30 ° C, such as polyethylene glycol, isopropanol, dimethyl sulfoxide, hydrogenated naphtha alenes and alkylated naphthalenes. Of course it is also possible to use mixtures of solvents. The solutions can be prepared in the usual way and, if necessary, use solution promoters funds. Other liquid forms which may be used consist of emulsions or suspensions of the active compound in water or suitable inert solvents, or concentrates for the preparation of positioning of such emulsions, which can be directly adjusted to the desired concentration. For this purpose you can, for example, mix it active ingredient with a dispersant or emulsifier The active component may also be dissolved or dispersed in a suitable inert solvent and simultaneously or thereafter mixed with a dispersant or emulsifier.

It is also possible to use semi-solid carriers ointment-like, paste-like or wax-like nature, in which the active the component is incorporated, if necessary, by means of solution-promoting agents and / or emulsifiers. Vaseline and other ointment bases are examples of semi-solid carriers.

It is also possible to use the active ingredient in form of aerosols. For this purpose, it is dissolved or dispersed active ingredient, if necessary by means of appropriate inert 10 15 20 25 30 35 NO 751264573 16 solvents such as carrier liquids, e.g. difluorodichloromethane, as in atmospheric pressure boils at a temperature below room temperature, or in other volatile solvents. In this way, solutions are obtained pressures which, when sprayed, produce aerosols which are particularly suitable for for the regulation or control of fungi, bacteria, e.g. in enclosed rooms and storage rooms, as well as for application to vegetation for the eradication or prevention of fungal or bacterial infections terier.

The present compounds and their compositions can be applied as with conventional methods. Fungi or bacteria or one materials to be treated or protected against fungal attack or bacteria, can be treated with the present compounds and com- its positions by dusting, sprinkling, spraying, brushing dipping, dipping, lubrication, impregnation or other suitable means.

When the present compounds were used together with suitable carriers, e.g. in solution, suspension, powder, powder, ointment, emulsion and similar forms, high activity is observed within a lot large dilution range. So, for example, have concentrations of it active ingredient of 0.1 to 10% by weight, by weight -of the composition used, proved effective in controlling fungi or bacteria. Of course, higher concentrations can also can be used if a certain situation gives rise to it.

The following examples are intended to illustrate, but not to limit, present invention. Unless otherwise stated, this applies to all parts parts by weight.

Example 1. A stirred and cooled (0 ° C) solution of 30 parts of 1- (β-amino- -2-methoxyphenyl) ethanone in 360 parts of concentrated hydrochloric acid solution, 175 parts of water and 30 parts of acetic acid are diazotized with a solution of 17.25 parts of sodium nitrite in 200 parts of water. After stirring in BG minutes at 0 ° C the whole is poured into a solution of 30 parts copper (I} - chloride in ZHO divides concentrated hydrochloric acid solution with stirring.

The mixture is heated for 1 hour at 60 ° C. When the product has cooled down at room temperature it is extracted twice with 2,2'-oxybispropane. The the combined extracts are washed successively with water, a dilute sodium hydroxide solution and then again twice with water, dried, filtered and evaporated to give 28 parts (76%) 1- (H-chloro-2-methoxyphenyl) ethanone, mp 55 ° C.

Example 2. A stirred solution of 78.8 parts of 2-bromo-1- (4-bromo-2-methyl- ylphenyl) -1-ethanone and 200 parts of butanol were added with 3 parts H-methylbenzenesulfonic acid and 225 parts of benzene. Then add 10 20 25 ~ 17 751264: -3 approximately 33.5 parts of 1,2-ecanediol. after fuiiboraad reaction continued The stirring is set overnight at reflux temperature with water. The reaction mixture is evaporated and the residue is dissolved The solution is stirred with 15 parts concentrated The layers are separated and the aqueous phase is extracted. The combined organic layers are washed separation. and 2,2 '-oxybispropane. sodium hydroxide solution. breed with 2,2'-oxybispropane. with water (for neutralization), dried, filtered and evaporated.

The solid residue is crystallized from methanol to give 50.5 parts of 2- (bromomethyl) -2- (4-bromo-2-methylphenyl) -1,3-dioxolane, m.p. 86 ° c.

Example 3. Following the procedure described in Example 2, ooh uses an equivalent amount of an appropriate 1-aryl-2-bromo-1-ethane instead of 2-bromo-1- (H-bromo-2-methylphenyl) -1-ethanone can follow the 2-aryl-2-bromomethyl-1,3-dioxolanes are prepared: 4- [2- (bromomethyl) -1,3-dioxolan-2-yl] -benzonitrile, mp 92 ° C, and 2- (bromomethyl) -2- (2-naphthanyl) -1,3-dioxolane, mp 6H ° C.

Example H. 57 parts of 1- (5-chloro-2-thienyl) -1-ethanone are dissolved in 220 parts 1,2-ethanediol at 5000. While stirring, add dropwise over one 1-hour period 6U shares bromine without external heating. After stirring for 1 hour at room temperature, H parts of U-methylbenzenesulfonate are added. acid and 360 parts benzene. The whole is stirred and refluxed over at night during separation of water. The reaction mixture is evaporated and the residue is taken up in 2,2'-oxybispropane. The solution formed wash successively once with dilute sodium hydroxide solution and three times with water, dried, filtered and evaporated. the remainder distilled to give 73.3 parts (64.5%) of 2- (bromomethyl) - -2- (5-chloro-2-thienyl) -1,3-dioxolane; boiling point 125-12706 at 13 Pa.

Example 5. Following the procedure described in Example H, and uses an equivalent amount of suitable 1-aryl-1-ethanone instead for 1- (5-chloro-2-thienyl) -1-ethanone, the following 2-aryl-2- (bromomethyl) - 1,3-dioxolanes are prepared: 2- (bromomethyl) -2- (9H-fluoren-2-yl) -1,3-dioxolane, mp 9000; 2- (bromomethyl) -2- (3-bromo-H-methylphenyl) -1,5-dioxolane, bp 126-13000 at 13 Pa; 2- (bromomethyl) -2- (U-iodophenyl) -1,3-dioxolane, mp 7U ° C; 2- (bromomethyl) -2- (H-chloro-2-methoxyphenyl) -1,3-dioxolane, mp 110 ° C, and 2- (bromomethyl) -2- (2,0-dibromophenyl) -1,3-dioxolane, mp 9600.

Example 6.

A. A stirred solution of 2.3 parts of sodium in 120 parts of methanol was added with 6.9 parts of 1H-1,2, U-triazole in 150 parts of dimethylformamide.

Q 10 15 20 25 30 35 H0 7512645-5 E, ¿8 The methanol is removed at normal pressure until the internal temperature rises. goes to 130 ° C. Then 25 parts of 2- (bromomethyl) -2- (2, ü- dichlorophenyl) -1,3-dioxolane. The reaction mixture is stirred and returned boiled for 3 hours. It is allowed to cool to room temperature and read in water. The precipitated product is filtered off and crystallized. in isopropyl ether (activated carbon) to give 12 parts 1- [2- (2,1H-dichlorophenyl) -1,3-dioxolan-2-ylmethyl] -1H-1,2,4-triazole, mp 10.9.9 ° C. _ B. 6 parts 1- [2- (2,1H-dichlorophenyl) -1,3-dioxolan-2-ylmethyl] -1H- 1,2 H-triazole was converted to the nitrate salt of 2,2'-oxybispropane. Ef- After cooling, the salt is filtered off and crystallized twice 2-propanone to give 3 parts of 1- [2- (2,1-dichlorophenyl) -1,3- dioxolan-2-ylmethyl] -1H-1,2,3-triazole nitrate, mp 17.7.7 ° C.

* C. 6 parts 1- [2- (2,1-dichlorophenyl) -1,3-dioxolan-2-ylmethyl] -1H- 1,2, H-triazole is converted to the sulphate salt in 2,2'-oxybispropane. The The sulphate formed is filtered off and crystallized from 2-propanol.

The product is filtered off and recrystallized from ethanol (activated carbon) whereby, after drying, 6 parts of 1 - ~2 ~ (2, H-dichlorophenyl) - 1,3-Alkiolan-2-ylmecyl-1H-1,2β-triazoisulfate, mp 207.1 ° C.

Example 7. A stirred solution of 2.3 parts of sodium in 80 parts of nol is added with 6.9 parts of 1H-1,2, U-triazole and 2 parts of sodium iodide in 100 parts N, N-dimethylformamide. The methanol is removed at ground pressure until the internal temperature reaches 130 ° C. Then 3N, H parts 2- (bromomethyl) -2- (2,0-dichlorophenyl) -N-methyl-1,3- dioxolane and the whole is stirred and refluxed for 3 hours. Reactive The ionic mixture is poured into water and the product is extracted twice with diisopropyl ether. The extract is washed with water and an excess of a conc. Salpeïefsyfalösninë is added- The crude nitrate salt 'is filtered off and crystallized from a mixture of 2-propanol and diisopropyl ether to give 15 parts of 1- [2- (2, H-dichlorophenyl) - 4-methyl-1,3-dioxolan-2-ylmethyl-1H-1,2,2H-triazole nitrate, mp 137.8 ° C.

Example 8. A stirred sodium methoxide solution, prepared starting from from 2.8 parts of sodium in H8 parts of methanol, was added with 8.3 parts of lar 1H-1,2, β-triazole. After stirring for 30 minutes at room temperature In turn, 55 parts of N, N-dimethylformamide are added and the methanol is evaporated.

Then a mixture of 2A, 3 parts of 2- (bromomethyl) -2-phenyl is added. yl-1,3-dioxolane and 3 parts of potassium iodide, and the whole is stirred and The reaction mixture is cooled to room temperature. temperature and poured into water. When scraping, the product fails.

It is sucked off, washed with water, dried and crystallized from one reflux for three hours. 15 20 Example 10. 7512643-3 19 mixture of ethanol and 2,2'-oxybispropane (1: 5 by volume), to give 10.9 parts (43.7%) of 1- (2-phenyl-1,3-dioxolan-2- yimeuyl) -in-1,2, u-uriazole, amp 127.3 ° c.

Example 9. Following the procedure described in Example 8, and uses an equivalent amount of a suitable 2-aryl-2- (bromomethyl) - 1,5-dioxolane instead of a 2- (bromomethyl) -2-phenyl-1,3-dioxolane, used in the example given, the following 1,2, H zolerz 2- (2- (nitrophenyl) -1,3-dioxolan-2-ylmethyl] -1H-1,2,4-triazole, mp 160.1 ° C; -1- [2- (3-chlorophenyl) -1,3-dioxolan-2-ylmethyl] -1H-1,2,1-triazole, mp 11.9 ° C; 2- (2- (bromophenyl) -1,3-dioxolan-2-ylmethyl-1,2-1,2-triazole, amp 135.9 ° C; 1 = [2- (3-methylphenyl) -1,3-dioxolan-2-ylmethyl] -1H-1,2,3-triazole, amp 105, M ° C; 1- [1- (3-bromophenyl) -1,3-dioxolan-2-ylmethyl] -1H-1,2, N-triazole, mp ll5, ë ° C, och 1- [2- (3-Nierophenyl) -1,3-aioxolan-2-ylmethyl] -1H-1,2,8-triazole, mp 15ß, 1 ° c.

A stirred sodium methoxide solution, prepared from from 1.6 parts of sodium in H8 parts of methanol, add H, 9 parts 1H-1,2, H-triazole. After stirring for 1 hour at room temperature In turn, 135 parts of N, N-dimethylformamide are added. The methanol is distilled at normal pressure until the internal temperature reaches 13006. Then successively add 17, ä parts 2 ~ (bromomethyl) ~ 2- (2,3, β-trichlorophenyl) -1,3-dioxolane and 3 parts of potassium iodide. The After cooling to When scraping Pro- whole ømröres and refluxed overnight. room temperature, the reaction mixture is poured into water. The product falls off, which is filtered off and washed with water. the product, dissolved in trichloromethane, is purified by column chromatography on silica gel using a mixture of trichloromethane and methanol such as eluent. The pure fractions are collected and eluted. the agent evaporates. the residue is crystallized from a mixture of 2,2'-oxybispropane and methanol (9: 1 by volume) to give holds 9.3 parts (55.5%) of 1- [2- (2,3-trichlorophenyl) -1,3-dioxolane-2- ylmethyl-1H-1,2, H-triazole, mp 181 ° C. äëempel ll. If you follow the procedure described in the example And uses equivalent amounts of suitable starting materials, the following 1,2,2-triazoles can be prepared: 1- [2- (9H: fluoren-2-yl) -1,3-dioxolan-2-ylmethyl] -1H-1,2,3-triazole, mp 18e, 80C; UI 10 15 -formamide. '20 7512643-5 1 - = [2- (s-kler-z-eigenylyl-1,5-nioxolan-z-ylmethyli-1fi- 1,2,6-triazole, mp 177 ° C; (2-bromo-N-methylphenyl) -1,3-dioxolan-2-ylmethyl-1H- 1,2,2-triazole, mp 120.7 ° C; 14 [ε = (H-bromo-2-methylphenyl) -1,5-dioxolan-2-ylmethyl] -1H- 1,2, H-triazole, mp 1N8.1 ° C, and 1-Ia- (H-chloro-2-methylphenyl) -1,3-dioxolan-2-ylmethyl] -1H- 1,2,2-triazole, mp 117.9 ° C. e Example gel 12. A stirred sodium methoxide solution, prepared starting from from 2.8 parts of sodium in 56 parts of methanol, add one mixture of 8.3 parts of 1H-1,2, H-triazole and 155 parts of N, N-dimethyl- The methanol is removed at normal pressure until its internal the temperature is 130 ° C. Then a mixture is added of 27.8 parts of 2- (bromomethyl) -2- (2-chlorophenyl) -1,3-dioxolane and 3 parts of lar potassium iodide. The whole is stirred and refluxed for 6 hours.

The reaction mixture is allowed to cool to room temperature, after which it nettle in water and the product is extracted three times with 1,1'-oxibis ~ ethane. The combined extracts are washed twice with water, dried, filtered and evaporated. The residue is transferred to the ethanedioate of N-methyl-2-pentanone. The salt is filtered off and crystallized from H-methyl-2-pentanone to give 16 parts of 1- [2- (2-chlorophenate) yl) -1,3-dioxolan-2-ylmethyl] -1H-1,2,4-triazole ethanediodate, mp 125.5 ° C.

Example 13 If following the procedure described in Examples 12, and uses equivalent amounts of suitable starting material, the following 1,2,4-triazolethane dicadate salts can be prepared: U 10 7512643-3 21 Ar Acid salt Melting point 2-Br-cH4 (coc. 17z.1 ° C). s-ocH3-c6H4 (coomz 155. 6'c. z-cn3-cóa4 (Coomz 177. 1 'c. 4-F-c¿H4 (common 1as.s ° c. 4-cH3-c6r14 (coomz - 151. z-c. 4- (21- C6H4 (coomz. H20 169. vc. 4-ocH3-c6H4 (coomz 187. 1 ° c.

Z-naphthalenyl (COOH) Z 17 5 ° C. i z, 5- (c1) 2-c6H3 (coomz 173.1 ° c. 4-cN-c6z-14 (coomz 186. 3 ° C. 3, 4- (c1) Z-C6H3 (coomz 182. z ° c.

Z-thienyl (COOPÛZ 144. 5 'C. 2,4- (Br) ¿-c6H3 (cool-na 190. 3 ° c.

Exemgel lä. A stirred sodium methoxide solution prepared from starting from 2.3 parts of sodium in H8 parts of methanol, add 6.9 parts of 1H-1,2,2H-triazole. temperature, 135 parts of N, N-dimethylformamide are added.

After stirring for 30 minutes at room temperature The methanol distilled at normal pressure until the internal temperature reaches to 130 ° C. Then 3 parts of potassium iodide and 16, parts 2- (bromomethyl) -2- (o-methoxyphenyl) -1,3-dioxolane. The entire stir and reflux for 18 hours. The reaction mixture is poured after cooling to room temperature in water and the solution formed The combined extracts are Re- extracted three times with trichloromethane. taken four times with water, dried, filtered and evaporated. the city is purified by column chromatography over silica gel, using turns a mixture of trichloromethane and 5% methanol as eluent average. The pure fractions are collected and the eluent is evaporated. the residue is converted to ethanedioate salts in U-methyl-2-pentanone.

The salt is filtered off and crystallized from a mixture of 2-propanone and 2,2'-oxybis-propane (2: 1 by volume) to give 5.5 parts (26%) of 1- [2- (2-methoxyphenyl) -1,3-dioxolan-2-ylmethyl] -1H- 1,2, u-criazol ethanedioate, mp 166, u ° c. §§§MEel_l§. If you follow the procedure described in the example using equivalent amounts of suitable starting materials, the following 1,2, H-triazole ethanedioate salts can be prepared: 1- [E- (M-iodophenyl) -1,3-dioxolan-2-ylmethyl] -1H- 1,2, U-triazole ethanediodate, mp 169.8 ° C; _, -_, ._...._._ .. ..., ...... ... fi ïm -... f-.l-rsv 10 15 20 25 39 75l2643-3 22 1- [2,3,5-dichlorophenyl) -1,3-dioxolan-2-ylmethyl] -1H- 1 ü ~ triazole ethanedioate, m.p. 20ü, H C: 1- [2- (6-dichlorophenyl) -, β-aioxolan-z-ylmethyl] -n- 132 U-triazole ethanedioate, mp 188, ü ° C; ( J ( 3 1 = [2- (4-chloro-2-methoxyphenyl) -1,3-dioxolan-2-ylmethyl] -1H- 1,4-triazole ethanediodate, mp 73.2 ° C; ( 5 IN 1-L2- (2,4,5-trichlorophenyl) -1,3-dioxolan-2-ylmethyl] -1H- 1,2 .alpha.-triazole ethanediodate, mp 178, H ° C, and 1 - (2 = .2-chloro-(methoxyphenyl) -1,3-dioxolan-2-ylmethyl] -1H- ¿2, fl = triazole ethanedioate, mp 188.2 ° C.

Example gel 16. A stirred mixture of 9.5 parts of 1H-1,2, H-triazole and 225 parts of N, N-dimethylformamide were added portionwise with ,2 parts of a sodium hydride dispersion (78%). The mixture is stirred until then smoke evolution ceases, after which 16 parts 2- (bromine) are added. methyl) -2- (2,1H-dichlorophenyl) -U-propyl, 1,3-dioxolane and the stirring ring continue for 5 hours at reflux temperature. Reaction mixture one is cooled and poured into water. The product is extracted three times The combined extracts are washed with water, dried, filtered and evaporated. the residue is purified by column chromatography over silica gel with a mixture of trichloromethane and 2% methanol as eluent. The first fraction is collected and eluted. the agent evaporates. The residue is converted into the nitrate salt in 2,2 * -oxy bispropane. The salt is filtered off and crystallized from a mixture of 2 = propanone and petroleum ether to give 8.2 parts (45%} [- = (2,4-dichlorophenyl) -H-propyl-1,3-dioxolan-2-ylmethyl] -1,2-1,2 triazole nitrate, mp 132.6 ° C. IN A stirred sodium methoxide solution prepared from 2,2'-oxybispropane.

Example 17. from 3.8 parts of sodium in H0 parts of methanol, was added with 11.5 parts 1H = 1,2, U-triazole and 225 parts N, N-dimethylformamide. Methano- The distillate is distilled off until the internal temperature reaches 150 ° C.

After the addition of 19 parts of 2- (bromomethyl) -2- (2,4-dichlorophenyl) -B-ethyl- 1,3-dioxolane, the whole is stirred and refluxed for N hours. Reactive The ionic mixture is cooled and poured into water. The product is extracted three times with 2,2'-okibispropane. The combined extracts are washed with water, dried, filtered and evaporated. column chromatography over silica gel with a mixture of trichloromethane and 2% methanol as eluent. The first fraction was collected and the eluent is evaporated. The residue is transferred to the nitrate the salt in 2,2'-oxybispropane. The salt is filtered off and recrystallized. in a mixture of H-methyl-2-pentanone and 2,2'-oxybispropane, 10.5 parts (H9%) of 1- [2- (2,0-dichlorophenyl) -β-ethyl- 1,3-dioxolan-2-ylmethyl] -1H-1,2,3-triazole nitrate, mp 11.8 ° C. the residue is purified with . .- -.-_- u - == .._ .. L .__.._-._ í __.._.._- nm-- - ..._..-. . ._ ..._ '_.-_ n ... fl nr.:rL-.=um'nuuu~r¶w:' "Å 10 9 .; LT! 7512645-3 ÉB âëgmgel 18. If you follow the procedure described in the example 17, and uses equivalent amounts of suitable starting material the following 1,2, H-triazolic acid addition salts can be prepared: 1- [N-butyl-2- (2,0-dichlorophenyl) -1,3-dioxolan-2-ylmethyl] -1H- 1,2, H-triazole-sesquietanedioate, mp 111.6 ° C; 1- [E- (2,3H-dichlorophenyl) -1H-pentyl-1,3-dioxolan-2-ylmethyl] -1H- 1,2, H-triazole nitrate, mp 130.3 ° C; 1- [1- (2,1-dichlorophenyl) -M-hexyl-1,3-dioxolan-2-ylmethyl] -1H- 1.2 triazole nitrate, mp 106.2 ° C; 1- (2,4-dichlorophenyl) -U-heptylal, 5-dioxolan-2-ylmethyl] -1H- 1,2,4-triazole nitrate, mp 96.8 ° C, and 1-Lä- (2,1-R-dichlorophenyl) -H-octyl-1,3-dioxolan-2-ylmethyl] -1H- 1,2, Ä-triazole nitrate, mp 110.6 ° C.

Example 19. By repeating the procedure of Example 6-A and replace 2- (bromomethyl) -2- (2, H-dichlorophenyl) -1,3-dioxolane with an equivalent valent amount of suitable 2- (bromomethyl) -2-aryl-1,5-dioxolane can be prepared the following compounds of formula (I): 1- [2- (2,6-trichlorophenyl) -1,3-dioxolan-2-ylmethyl] -1H-1,2,3-triazole; 1- [Q- (2,6-dichlorophenyl) -1,3-dioxolan-2-ylmethyl] -1H-1,2,2-triazole; 1- [2- (2-chloro-4-methylphenyl) -1,3-dioxolan-2-ylmethyl] -1H-1,2,3-triazole.

Example Gel 20. The procedure of Example 7 can be used to prepare compounds of formula (I), wherein Z represents -CH 2 -CH (CH 3) - or -CH (CH 3) -CH (CH 3) -. Consequently, by inserting one equivalent amount of suitable 2-aryl-2- (bromomethyl) -U-methyl-1,3-dioxolane or 2-aryl-2 «(bromomethyl) -1,5-dimethyl-1,3-dioxolane compounds in the form of the nitrate salt: 1- (U-methyl-2-phenyl-1,3-dioxolan-2-ylmethyl) -1H-1,2,3-triazole; 1- [2 = (N-chlorophenyl) -1H-methyl-1,3-dioxolan-2-ylmethyl] -1H-1,2,2-triazole; 1-fa- (2-chlorophenyl) -H-methyl-1,3-dioxolan-2-ylmethyl] -1H-1,2,1-triazole; 1-Za-methyl-2- (4-methylphenyl) -1,3-dioxolan-2-ylmethyl] -1H-1,2,1-triazole; leze- (β-methoxyphenyl) -M-methyl-1,3-dioxolan-2-ylmethyl] -1H-1,2,4-triazole; 1-N, 5-dimethyl-2- (2,3H-dichlorophenyl) -1,3-dioxolan-2-ylmethyl 1,2, H "triazole; (5-dimethyl-2-phenyl-1,3-dioxolan-2-ylmethyl) -1H-1,2,4-triazole and - N- (H-chlorophenyl) -H, 5-dimethyl-1,3-dioxolan-2-ylmethyl] -1H- 1,2, H-triazole. §§Gg2gl_§l. The procedure described in Example 6-A can be used for the preparation of the compounds of formula (I) wherein Z represents -CH2-CH2-CH2-. Consequently, by inserting an equivalent amount of suitable 2-aryl-2- (bromomethyl) -1,3-dioxane seam starting material obtain the following compounds: 1- (2-phenyl-1,3-dioxan-2-ylmethyl) -1H-1,2,2-triazole; 1 l a 10 15 20 25 75í2643 ~ 3 24 1- [2- (2,H-dichlorophenyl) -1,3-dioxan-2-ylmethyl-1H-1,2,3-triazole 1- [2- (N-chlorophenyl) -1,1-Bedioxan-2-ylmethyl] -1H-1,2,2-triazole; 1- [ε- (U-methylphenyl) -1,3-dioxan-2-ylmethyl] -1H-1,2,3-triazole; 1 = {2- (4-methoxyphenyl) -1,5-dioxan-2-ylmethyl-1H-1,2,1H-triazole; 1- [2- (z-thienyl) -1,2-dioxan-z-ylmethyl] -1-1,2fa-triazole and 1- [2- (2-naphthyl) -1,5-dioxan-2-ylmethyl] -1,2,2,4-triazole.

Example Gel 22. The compositions of the present invention use were in the forms commonly used to control fungi or bacteria, e.g. such as suspensions, powders, solutions, creams more and the like. The following examples are intended to further illustrate the invention and the parts are by weight unless otherwise indicated: (1) Suspension 1 kg 1- [2- (2,1-dichlorophenyl) -1,3-dioxolan-2-ylmethyl] 1H-1,2,2, triazole _2 lit. technically xylene 350 ml surfactant _ water is diluted to the desired concentration of active stand. , 1- [2- (2,4-dichlorophenyl) -1,3-dioxolan-2-ylmethyl] -1H-1,2,2-tri- the azole forms a stable aqueous suspension when dissolved in xylene and emulsified with a surfactant. (2) Means of promotion: 20 parts of 1sl- (2,3H-dichlorophenyl) -1,3-dioxolan-2-ylmethyl] -1H- 1,2, ü-triazole is ground with 360 parts of talc in a ball mill, after which 8 parts olein are added and grinding is continued and finally mixed das the mixture with U parts quenched lime. The powder formed can sprnt satisfactorily and has good adhesion. It can be used for powdering or for protecting plants. (3) Solution: 5 parts 1- [2- (2,4-dichlorophenyl) -1,3-dioxolan-2-ylmethyl] -1H- 1,2, α-triazole is dissolved in 95 parts of alkylated naphthalene and is thus used. as a spray for the treatment of fungal-infected objects or on the road floors, floors or other objects to prevent fungal infection. o (i) 53% * 10 parts 1- [1- (2,1-dichlorophenyl) -1,3-dioxolan-2-ylmethyl] -1H- 1,2,6-triazole is dissolved in a hot liquid mixture of ÄGO parts poly- ethylene glycol H00 and 590 parts of polyethylene glycol 1500. The solution Stirred under cooling and used as a cream for treating fungus couples and bacteria. sanna -___ __ _..- ~ _ .___.__...-... »_... ~., ...._-...-.-_ 1-.m -_ = v ~ _ 1.1. ", ,, _._. ~ - 75126 43-3 25 Example 23.

W ~~ N n \ N /> M-methylbenzene- OCH- w. _.- _ "sulfonic acid C åH3_å_¿êñ_ + HO ”d2” hä “HEOH mecylbenzene U 5 - 3 Y _31 B (amy f, Lä) -Hr fl s- / jfz-CHB Cl [T__F ï * '01 \ m2 f / (f \ = -c1 y »J - HNOE ß A mixture of 1.7 parts of 1,3-propanoyl, 1 part of H-methylbenzene ulfonic acid and 3; parts of methylbenzene are stirred and refluxed Leeward 1 minute with water separator. Then add 7.1 parts 1- gr] 1 ' sensulfana: and stirring under reflux is continued for Ä hours.

FU (fl-dit) phenyl) -2,2-dimethoxyethyl-1H-1,2,4-triazole-M-methylbenzyl The reaction mixture is cooled, diluted with 1,1-oxybisethane and all fi Hydrogenate with a dilute sodium hydroxide solution and with water. One - concentrated hydrochloric acid solution is added, after which the nitrate salt zvfiltered and crystallized from a mixture of 21 2,2'-oxybispropane to give 2.2 parts (39%) OUT 7512643-3 26 Example EU.

T - N m! J I “\}, OH QH 4-? Ethyl1benzene- * AND? _ A _ _, _ _ _ su fonsyra C «L i ¿oxå G sozoh + cnš on cH CHB methylbenzene D LH “u“ ObH 2 l 3 (HNO> \ _í§ Cl A 'lg IN 1 NW) o_ IN CH2 -Cl HNO o o 5 H30 CH3 A mixture of 1.8 parts of 2,3-butanediol, 1 part of Ä-methylbenzene sulfonic acid and 90 parts of methylbenzene are azeotroped to dry ~ it (1 hour). Then 7.1 parts of 1-É- (2,1-dichlorophenyl) - are added. 2,2-dimethoxyethyl-1H-1,2,1-triazole-U-methylbenzenesulfonate and stirred The reaction mixture is cooled The product is extracted with overnight at reflux temperature. and diluted with a sodium hydroxide solution. 1,1'-oxybispropane. The extract is washed with water, dried, filtered The residue is transferred to the nitrate salt in the 2,2 ' The salt is filtered off and crystallized from a mixture and inhale. oxibispropane. acetonitrile and 2,2'-oxybispropane. The product is filtered off and dried to give 4.6 parts of 1- [ε- (2,4-dichlorophenyl) -1,5-dimethyl-1,3- dioxolan-2-ylmethyl7-1H-1,2,4-triazole mononitrate; melting point 125 ° C.

Claims (6)

to 7512643-3 Patent claims A chemical compound having a fungicidal, bactericidal or plant-regulating use, characterized in that it consists of a 1- (6-aryl) -ethyl-1H-1,2,4-triazole ketal of the formula NI or therapeutically active acid addition salts thereof, wherein Z represents alkylene consisting of -CH 2 -CH 2 -, -QH 2 -CH 2 -CH 2 -, -CH (CH 3] -CH (CH 3) - or -CH 2 -CH (alkyl) -, wherein the alkyl group has 1 to 10 carbon atoms, and Ar represents 2,4-dihalophenyl. Compound according to Claim 1, characterized in that it consists of 1- [ε- (2,4-dichlorophenyl] -1,3-dioxolan-2-ylmethyl] -1H-1,2,4-triazole or therapeutically active acid addition salts thereof. A compound according to claim 1, characterized in that it is 1- (5- (2,4-dichlorophenyl) -4-methyl-1,3-dioxolan-Zylmethyl] -1H-1,2,4- triazole or therapeutically active acid addition salts thereof. A compound according to claim 1, characterized in that it is 1-12- (2,4-dichlorophenyl} -4-ethyl-1,3-dioxolan-2-ylmethyl-1H-1,3,4 -triazole or therapeutically active acid addition salts thereof. A compound according to claim 1, characterized in that it consists of 1-La- (2,4-dichlorophenyl) -4-propyl-1,5-dioxolan-2-ylmethyl-1H-1,2,4- triazole or therapeutically active acid addition salts thereof. 6. A compound according to claim 1, characterized in that it is 1-α- (2,4-chlorophenyl) -4-penyl] -1,1-s-oxo [1an-z-ylmethyl] -1H-1 2,4-triazole or therapeutically active acid addition salts thereof. ANFURDA PUBLICATIONS: SE 349 037 (C07d 55/06) DE 2 247 186 (A61K 27/00) US 3 575 999 (26Û ~ 3Û9), 3 755 349 (260-309)