JPS6344155B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention is based on the formula In the formula, R ¹ and R ² are each independently selected from the group consisting of hydrogen and halogen, R ³ is hydrogen, and at least one of R ¹ and R ² is a halogen; Q is is a member selected from the group consisting of CH and N; X, Y and Z are each independently selected from the group consisting of hydrogen and _C1 - _C4 alkyl, with the condition that
and 1-(2-aryl-1,3-dioxan-2-ylmethyl)-1H-imidazole and at least one of Z is other than hydrogen.
1H-1,2,4-triazole derivatives and their pharmaceutically acceptable acid addition salts, metal salt complexes and stereochemically isomeric forms for plants. Compounds suitable within the scope of the invention are those in which X, Y and Z together consist of at most 10 carbon atoms and R ¹ and R ³ are hydrogen, chloro or bromo and R ² Compounds that are chloro or bromo. Particularly preferred compounds within the scope of the invention are X, Y
and Z together of at most 5 carbon atoms, R ² is chloro, and R ¹ and R ³ are hydrogen, and both R ¹ and R ² are chloro, and A compound in which R ³ is hydrogen. Further preferred compounds within the scope of the present invention are X, Y
and Z are compounds in which neither has more than 3 carbon atoms. The most preferred compounds within the scope of the invention are those in which R ¹ and R ² are chloro and R ³ is hydrogen;
R ² is chloro, R ¹ and R ³ are hydrogen, none of X, Y and Z have more than 3 carbon atoms, and two of them are 1,3-dioxane nuclei. A compound bonded to a carbon atom in the 5-position. Halogen as used in the above definition is a generic term for fluoro, chloro, bromo and iodo: "C ₁ -C ₄
The term "alkyl" is meant to include straight and branched chain hydrocarbon groups having from 1 to 4 carbon atoms, such as methyl, propyl, 1-methylethyl, 1,1-dimethylethyl, and the like. A compound of formula () is generally a compound of formula (), with the proviso that Q
is as defined above, and Me is hydrogen,
4-substituted ammonium ions, such as tetra(C ₁ -C ₆ -alkyl)ammonium, tri(C 1 -C _{6 -alkyl} )
C ₆ -alkyl)ammonium, etc., or preferably a metal atom, such as potassium, sodium, etc., with the formula R ¹ , R ² , R ³ , X,
It can be prepared by reacting with a halogenide, where Y and Z are as defined above and T is halogen, preferably chloro, bromo or iodo. The reaction between formulas () and () is preferably carried out in a relatively polar reaction with an inert organic solvent, e.g.
Dimethylformamide, N,N-dimethylacetamide, dimethyl sulfoxide, acetonitrile,
It is carried out in benzonitrile etc. Such solvents can be used in combination with inert solvents in other reactions, such as aliphatic or aromatic hydrocarbons such as benzene, methylbenzene, dimethylbenzene, hexane, petroleum ether, chlorobenzene, nitrobenzene, and the like. When T represents chloro or bromo, the reaction can advantageously be carried out in the presence of an alkali metal iodide, such as sodium or potassium iodide, in order to increase the reaction rate. About 30 to about 220℃, preferably about 80 to about
A temperature increase of 170° C. is suitable and the reaction is advantageously carried out under reflux. When Me represents hydrogen, the reaction is carried out in the presence of a base. Suitable bases that may be utilized include alkali metal oxides, hydroxides, carbonates and bicarbonates, and tertiary amines such as N,N-diethylethanamine, pyridine, and the like. In view of its basic properties, azole () can be used to accelerate the reaction when added in excess. In the above and following processes, the reaction product can be isolated from the medium and, if necessary, by methods generally known in the art, for example by extraction, disintegration, crystallization, chromatography, etc. It can be further purified. Suitable acids for forming salts are plant- or physiologically acceptable acids, respectively, such as inorganic acids,
For example, hydrochloric acid, hydrobromic acid, hydroiodic acid,
Sulfuric acid, phosphoric acid, phosphonic acid, nitric acid, etc., organic acids such as trifluoroacetic acid, trichloroacetic acid, benzenesulfonic acid, methanesulfonic acid, etc. Metal salt complexes of formula () are composed of azoles of formula () and organic or inorganic metal salts, such as copper, manganese,
Hydrohalides, nitrates of transition metals, such as zinc, iron, etc., which may exist in each of their possible valences;
It can be obtained by complexing reaction with sulfate, phosphate, 2,3-dihydroxybutanedioate, etc. Stoichiometrically defined metal salt complexes can be prepared by dissolving a compound of formula () in a water-miscible solvent (e.g. warm ethanol, methanol, 1,4-dioxane or N,N-dimethylformamide) and adding the desired Metal salts such as CuSO ₄ 5H ₂ O, Mn
(NO ₃ ) It can be produced by adding solutions such as _{2.4H 2} O, FeCl _{3.6H 2} O, etc. Those listed above are for illustrative purposes only;
It is not intended to limit the scope of the invention. The intermediates of formula () used as starting materials in the above reactions are generally known in the art. Intermediates of formula () can be prepared by converting the appropriate acetophenone derivative of formula () according to methods known in the art for preparing such or similar compounds, e.g., according to acetalization methods known in the art. ) can be produced by acetalizing with a suitable 1,3-diol. In the above reaction formula, R ¹ , R ² , R ³ , X, Y
and Z are as defined above and L represents hydrogen or the group T. When L represents hydrogen,
This L-group is converted to a halo group before, during or after acetalization according to halogenation methods known in the art. The acetalization reaction is preferably carried out by stirring and heating the reactants together in an inert solvent such as benzene, methylbenzene, etc., preferably in the presence of a catalytic amount of a suitable acid, such as 4-methylbenzenesulfonic acid. This can be easily done by Most preferably, the reaction is carried out with azeotropic distillation of water liberated during the reaction process. In addition, the acetal of formula () can be obtained from other cyclic or alicyclic acetals by using an excess amount of 1,3-diol ().
The corresponding desired acetal can be derived by reacting with. By formula (), the compounds of the present invention have at least one asymmetric carbon atom in their structural formula, and some of the compounds have 1, It is clear that the 3-dioxane has one or more additional asymmetric carbon atoms within the nucleus and can therefore exist in different stereochemically isomeric forms. Stereochemically isomeric forms of formula () as well as its plant pharmaceutically acceptable acid addition salts and metal salt complexes are intended to be included within the scope of this invention. Diastereomeric racemates of formula () can be obtained separately by conventional methods. Suitable methods which may be advantageously used therefore include, for example, fractional crystallization and chromatographic preparation, such as column chromatography. Since the stereochemical configuration is already fixed in the intermediate (), the diastereomeric racemate can be separated at this stage, from which the formula () can be separated in the manner already shown.
The corresponding form of can be derived. Separation of the diastereomeric racemates of such intermediates can be carried out by conventional methods such as those already described for the separation of the diastereomeric racemates of compound (). In particular, the compounds of formula () are highly advantageous anfimicrobial agents which make them useful for crop protection without undesirable side reactions.
It has a spectrum. Examples of crops included within the scope of the invention are: cereals, corn, rice, vegetables, sugar beets, soybeans, peanuts,
Fruit trees, ornamentals, vines, hops, Cucurbitaceae (gherkins, cucumbers, melons), Solanaceae such as potatoes, tobacco and tomatoes, and bananas, cocoa and gum. Compounds of formula () may be added to the plants mentioned above or related crops or parts of such plants such as fruits, flowers, leaves, etc.
They can be used to reduce or eradicate fungal growth on stems, tubers, roots) and thus also protect newly growing parts of such plants against fungal attack. The compounds of the invention are active against phytopathological fungi belonging to the following species: Ascomycetes (e.g. Erysiphaceae, Fusarium);
Venturia, Helminthosporium); Basidiomycetes, especially rust fungi (e.g. Puccinia); Fungiimperfecti (e.g. Moniliales, etc.) , Cercospora and Botrytis)
and Phycomycetes, such as Oomycetes belonging to the species of the genera Phytophthora and Plasmopara. Additionally, the compounds can be used as seed smears in the treatment of seeds (e.g. fruits, tubers, grains) and as cuttings to protect seeds from fungal infections, and against fungi in the soil. can. Gray mold species (Botrytis cinerea, Botrytis
allii) causes extremely economical damage to fruits and vegetables such as grapes, strawberries, apples, bulbs, etc. due to the gray fungus. Compounds of formula () can be used alone or in combination with suitable carriers and/or additives. Suitable carriers and additives can be solid or liquid and are generally those known in the field of preparation manufacturing, such as natural and recycled mineral substances, solvents, dispersants, adhesives, thickeners, binders or fertilizers. be. The concentration of active ingredient in commercial preparations ranges from about 0.1 to about
It can be in the range of 90%. For its application, the compounds of formula () can be made into preparations in the following compositional forms (wherein the appropriate concentrations of active ingredients are indicated in parentheses): Solid preparations: Dusts (up to 10%) , granules, coated granules, impregnated granules and homogeneous granules,
Pellets (1-80%); Liquid preparations: (a) Water-dispersible concentrates; Wettable powders and liniments (25-90% for commercial use, 0.01% for prepared solutions)
~15%); emulsions and concentrated solutions (10-50%; 0.01-15% for prepared solutions); (b) solutions (0.1-20%);
%); aerosol. If necessary, the compound of formula () may be combined with other suitable insecticides, such as fungicides, bactericides, insecticides, acaricides, herbicides, plant growth regulators, etc., in order to widen the range of activity. can do. The following examples illustrate the invention:
It is not intended to limit the scope of the invention. All temperatures are given in degrees Celsius (°C). A Chemical Preparation Examples Example 1 To a stirred sodium methylate solution prepared starting from 3.7 parts of sodium in 40 parts of methanol, 10.8 parts of 1H-imidazole and 270 parts of N,N-dimethylformamide were added. internal temperature
Methanol was distilled off until the temperature reached 150°C. Next, 19 parts of A+B-2-(bromomethyl)-2-(2,4-dichlorophenyl)-5-ethyl-1,3-dioxane were added and the whole was stirred and refluxed for 5 hours. The reaction mixture was cooled and poured into water. The product was extracted three times with 1,1'-oxybisethane. The combined extracts were washed with water, dried, filtered and evaporated. The residue was placed on silica gel.
Purified by column chromatography; the first fraction was collected eluting with a mixture of trichloromethane and 2% methanol. The eluent was evaporated and the residue was dissolved in 4-methyl-2-pentanone and 2,
Converted to nitrate in 2'-oxybispropane. The salt was separated and crystallized from a mixture of 4-methyl-2-pentanone and 2,2'-oxybispropane, A+B-1-[2-(2,4-dichlorophenyl)-5-ethyl-1 , 3-dioxan-2-ylmethyl]-1H-imidazole nitrate 5.8 parts (26.5
%) was obtained: melting point 145.1°C. Example 2 (a) 1-(2,4-dichlorophenyl)ethanone,
35 parts of 2-ethyl-1,3-hexanediol,
A mixture of 2 parts of 4-methylbenzenesulfonic acid and 400 parts of methylbenzene was refluxed with a water separator attached. After cooling, the reaction mixture was diluted with 200 ml of water.
Washed twice, dried over sodium sulphate, filtered and evaporated. To a solution of the remaining oil refluxing in methylbenzene was slowly added 33.6 parts of bromine at such a rate that the reaction mixture spontaneously decolorized, and the mixture was then refluxed for 1 hour. The cooled reaction mixture was washed twice with water, dried, filtered and evaporated. 2-(bromomethyl)-2-(2,4-dichlorophenyl)
The remaining oil consisting of -5-ethyl-4-propyl-1,3-dioxane was purified by distillation; boiling point 150-153°C/0.03 mmHg. (b) 2-(bromomethyl)-2-(2,4-dichlorophenyl)-5-ethyl-4-propyl-1,
23 parts of 3-dioxane, 5.6 parts of imidazole and 100 parts of dimethyl sulfoxide were mixed with 9.3 parts of potassium t-butyrate and the whole was stirred at 130 DEG C. for 16 hours. Pour the cooled mixture into 500 parts of water,
Extraction was performed three times with 300 parts of 1,1'-oxybisethane. The combined organic layers were washed with 300 parts of water, dried and evaporated. The remaining oil was purified by column chromatography on silica gel using ethyl acetate as eluent. The pure fractions were collected, the eluent was evaporated and the 1-[2-(2,4-dichlorophenyl)-5-
Ethyl-4-propyl-1,3-dioxane-
A diastereomeric mixture of 2-ylmethyl]-1H-imidazole was obtained; ^n23D : _1.5486 . Following the method described above and using equivalent amounts of the appropriate starting materials, the following were prepared:

【table】

【table】

Table Example 3 A mixture of 2 parts of 2,2-dimethyl-1,3-propanediol, 1 part of 4-methylbenzenesulfonic acid and 90 parts of methylbenzene was distilled azeotropically for 1 hour to dryness. Then 1-[2-(2,4-dichlorophenyl)-2,2-dimethoxyethyl]-
7.1 parts of 1H-1,2,4-triazole 4-methylbenzenesulfonate were added and stirring under reflux was continued for 6 hours. The reaction mixture was cooled, washed sequentially with dilute sodium hydroxide solution and water, dried,
filtered and evaporated. The residue was converted to the nitrate in 2,2'-oxybispropane. The salt was separated, dried and 1-[2-(2,4-dichlorophenyl)-5,5-dimethyl-1,3-dioxan-2-ylmethyl]-1H-1,2,4-triazole 4.8 parts (79%) of nitrate were obtained; melting point 130.6°C. Following a similar method above and using equivalent amounts of the appropriate starting materials, the following were prepared:

【table】

[Table] Example 4 (a) 1-(2,4-dichlorophenyl)-ethanone
56.7 parts, 1,3-butanediol 32.4 parts, 4-
A mixture of 2 parts of methylbenzenesulfonic acid and 400 parts of methylbenzene was stirred and refluxed for 5 hours using a water separator. After cooling, the reaction mixture was washed with water, dried, filtered and evaporated. 49.6 parts of bromine was slowly added to the oily residue taken in refluxing trichloromethane.
After the addition of bromine was complete, the mixture was stirred and refluxed for 1 hour. After cooling, the reaction mixture was washed twice with water, dried, filtered and evaporated.
The remaining yellow oil is dissolved in cold petroleum ether (boiling point 40-60
2-(2,4-dichlorophenyl)-2-
Crystals of a diastereomeric mixture of (bromomethyl)-4-methyl-1,3-dioxane were obtained. ; Melting point 69-70.5°C. (b) 10.8 parts of potassium carbonate, 5.4 parts of 1H-1,2,4-triazole, 2-(2,4-dichlorophenyl)-2-(bromomethyl)-4-methyl-1,
3-dioxane 20.5 parts, sodium iodide 0.2
part and 100 parts of dimethyl sulfoxide.
The mixture was stirred at 100°C for 36 hours, cooled, and poured into 600 parts of water. The reaction mixture was extracted three times with ethyl acetate and the combined organic layers were washed with 200 parts of water, dried, filtered and evaporated. The remaining oil was purified by column chromatography on silica gel using ethyl acetate as eluent. Collect the pure fraction, evaporate the eluent, and
-[2-(2,4-dichlorophenyl)-4-methyl-1,3-dioxan-2-ylmethyl]
-1H-1,2,4-triazole was obtained; n _D ^2
2 :1.5505. B Preparation Examples Example 5 Dusts: (a) 25% and (b) 2% To prepare the dusts, the following substances were used: (a) Active substance 5 parts Talc 95 parts (b) Active substance 2 parts highly dispersed silicic acid 1 part talc 97 parts The active substance could be mixed with the carrier and ground to form a powder for application in this state. Example 6 Granules: The following materials were used to produce a 5% powder: Active substance 5 parts epichlorohydrin 0.25 parts cetyl polyglycol ether 0.25 parts polyethylene glycol 3.25 parts kaolin (particle size 0.3-0.8 mm) 91 parts of active substance were mixed with epichlorohydrin and this mixture was dissolved in 6 parts of 2-propanone. Next, polyethylene glycol and cetyl polyglycol ether were added. The resulting solution was sprayed onto kaolin and the 2-propanone was evaporated under vacuum. Such granules are advantageously used in eradicating soil fungi. Example 7 Wettable powder: (a) 70%, (b) 40%, (c) and (d) 25% and
(e) To prepare a 10% hydrating powder, the following ingredients were used: (a) Active substance 70 parts sodium dibutylnaphthylsulfonate
5 parts naphthalenesulfonic acid/phenolsulfonic acid/formaldehyde condensate (3:2:1)
3 parts kaolin 10 parts Champagne chalk
12 parts (b) Active substance 40 parts sodium lignin sulfonate 5 parts sodium dibutylnaphthalene sulfonate
1 part Silicic acid 54 parts (c) Active substance 25 parts Calcium lignin sulfonate 4.5 parts Champagne color/hydroxyethylcellulose mixture (1:1) 1.9 parts Sodium dibutylnaphthalene sulfonate
1.5 parts Silicic acid 19.5 parts Champagne color 19.5 parts Kaolin 28.1 parts (d) Active substance 25 parts Iso-octylphenoxy-polyethylene-ethanol 2.5 parts Champagne pigment/Hydroxyethylcellulose mixture (1:1) 1.7 parts Sodium aluminum silicate 8.3 parts diatomaceous earth 16.5 parts kaolin 46 parts (e) Active substance 10 parts sodium salt mixture of saturated aliphatic alcohol sulfates 3 parts naphthalene sulfonic acid/formaldehyde condensate 5 parts kaolin 82 parts. The active substance is thoroughly mixed with the additives in a suitable mixer and ground in a suitable mill and rolls. Wettable powders and suspension powders with outstanding wetting properties were obtained. This wettable powder could be diluted with water to give a suspension of the desired concentration and could be used in particular for foliar applications. Example 8 Emulsifiable concentrate: To prepare a 25% emulsifiable concentrate, the following materials were used: Active substance 25 parts epoxidized vegetable oil 2.5 parts alkylaryl sulfonate/fatty alcohol polyglycol ether mixture 10 parts dimethylformamide 5 parts dimethylbenzene 57.5 parts By diluting the above concentrate with water, an emulsifier of the desired concentration can be prepared, which is particularly suitable for foliar application. C Biological Examples Example 9 Cercospora blight in peanut plants
personata) [= Cercospora
arachidicola)] Peanuts three weeks after germination were sprayed with a spray solution prepared from a wettable powder of the active substance (containing 0.02% of the active substance). Approximately 12 hours later, the treated plants were infected by sprinkling with a suspension of fungal conidia. Infected plants were incubated at 22° C. with high relative humidity (>90%) for approximately 24 hours and then placed in a glass house. Fungal infection was evaluated 12 days after infection based on the number and spread of spots appearing. Compared to untreated plants, plants treated with compounds of formula () showed only limited growth or no growth of fungi. Example 10 Downy mildew in grapevines (Plasmopara
viticola) (Bert. and Curt.) (Berl.et De
Activity against three grape seedlings with 10 leaves ('Chasselas')
seeds) were sprayed with a spray solution prepared from a wettable powder of the active substance (containing 0.06% active substance). After drying of the spray, the undersides of the leaves of the plants were infected with a suspension of fungal sporangia and then placed in a humid chamber for 8 days. After this period, untreated plants showed constant fungal growth. The extent of fungal infection was assessed based on the number and spread of spots that appeared. Compound No. 1.9, 1.16,
1.19, 1.21, 2.9, 2.10, 2.11, 2.16 and similar compounds completely inhibited fungal growth. Example 11 Powdery mildew in barley (Erysiphe
(a) Long-lasting protective action Spray solution prepared from a wettable powder of the active substance (containing 0.02% of the active substance) on barley plants approximately 8 cm in height.
was sprayed. After 3-4 hours, the treated plants were sprinkled with fungal conidia. Infected barley plants were placed in a glass house at approximately 22°C and fungal erosion was assessed 10 days after infection. (b) Tissue action A spray solution prepared from a hydrating powder of the active substance (containing 0.006% of the active substance; the amount is proportional to the soil volume) is applied to barley plants 8 cm high, but the external parts of the plants are not sprayed. Care was taken to avoid contact with the liquid. After 48 hours, the treated plants were sprinkled with fungal conidia. Infected barley plants were placed in a glass house at 22°C and fungal infection was assessed after 10 days. Test (a): The compound of formula () completely inhibited fungal growth. Compound No. 1.9, 1.10, 1.11,
1.16, 1.21, 2.9, 2.10, 2.11, 2.16, 2.27,
2.31 and similar compounds showed complete inhibition even at a concentration of 0.0006%. Test (b): Compounds No. 1.16, 2.9, 2.11 and similar compounds showed complete inhibition of fungal growth. Compounds of formula () and especially 1H-1,2,4
- Triazole derivatives were particularly active in protection against powdery mildew (Erysiphe spp.). Example 12 Gray mold disease (Botrytis) in fava beans
cinerea) Broad bean plants approximately 10 cm high were sprayed with a spray solution prepared from a wettable powder of the active substance (containing 0.02% of the active substance). After 48 hours, the treated plants were infected with a suspension of fungal conidia. Infected plants at relative humidity of 95
Fungal infection was assessed after 3 days of incubation at ~100% and 21°C. A significant number of compounds of formula (), such as compounds No. 1.9, 1.10, 1.11, and 1.21, completely inhibited fungal growth at concentrations of 0.006% and below. Example 13 Active residual protective effect against Hemileia vastatrix in coffee trees Coffee plants approximately 15 cm in height were sprayed with a spray solution prepared from a wettable powder of the active substance (containing 0.06% of the active substance). . After 24 hours, the treated plants were infected with a suspension of rust spores. Infected coffee plants were placed in a humid chamber for 48 hours and then placed in a glass house at 22°C until rust pustules appeared (approx.
week). The reduction in the number of rust pustules was a measure of the activity of the test substance. The compound of formula () exhibited complete protection at the concentrations indicated. Compound No.2.9, 2.10,
2.11, 2.16 etc. showed complete protective effect at a concentration of 0.002%. Example 14 Venturia scab in apple seedlings
Apple seedlings 10-20 cm high were sprayed with a spray solution prepared from a wettable powder of the active substance (containing 0.06% active substance). After 24 hours, the treated plants were infected with a suspension of fungal conidia. Next, this plant is placed at a relative humidity of 90
Cultured at ~100% followed by incubation in a hotbed at 20-24 °C for 10 days. Fungal infection was assessed on day 15 post-infection. The 1H-1,2,4-triazole derivative of formula () exhibited complete protection at the indicated concentration of 0.06%. Even at an extremely low concentration of 0.006%, Compound No.
2.9, 2.10, 2.11, 2.16 and similar compounds showed full activity. Example 15 Black rust in wheat (Puccinia
Activity (a) Long-lasting protection against wheat plants 6 days after sowing with a spray solution prepared from a wettable powder of the active substance (active substance
0.06%) was sprayed. After 24 hours, the treated plants were infected with a suspension of fungal diaspores. After 48 hours of incubation at 90-100% relative humidity and approximately 20°C, the plants were placed in a greenhouse at approximately 22°C. The development of rust fungus pustules was evaluated on day 12 post-infection. The compound of formula () showed complete inhibition of fungal growth. Even at a low concentration of 0.006%, compound No. 2.10,
2.16, 2.27 and 2.31 showed complete inhibition. (b) Tissue action A spray solution prepared from a wettable powder of the active substance (0.006 g of active substance) was applied to wheat plants 5 days after sowing.
% content; spray amount is proportional to soil volume). After 3 days, the treated plants were infected with a suspension of fungal diaspores. Relative humidity 95-100% and
After 48 hours of incubation at 20°C, the treated plants were approximately 22
It was placed in a glass house at ℃. Rust fungus pustules were evaluated on day 12 postinfection. Compounds with formula (), such as Compound Nos. 2.9 and 2.10, completely inhibit fungal growth through tissue action, and Compound No.
2.11 showed full activity even at a concentration of 0.002%. Biological Examples 9 to 15 show that compounds of formula (), especially 1H
-1,2,4-triazole acetals demonstrate great potency and wide spectrum of activity.

Claims (1)

[Claims] 1 formula In the formula, R ¹ and R ² are each independently selected from the group consisting of hydrogen and halogen, and the conditions are that R ¹ and R ²
Q is a member selected from the group consisting of CH and N; X, Y and Z are each independently selected from the group consisting of hydrogen and C ₁ -C ₄ alkyl; , the conditions are X, Y
and 1-(2-aryl-1,3-dioxan-2-ylmethyl)-1H-imidazole and at least one of Z is other than hydrogen.
A compound selected from the group consisting of 1H-1,2,4-triazole derivatives and their pharmaceutically acceptable acid addition salts, metal salt complexes and stereochemical isomers. 2. A compound according to claim 1, wherein R ¹ is hydrogen, chloro or bromo and R ² is chloro or bromo. 3 R ² is chloro and R ¹ is hydrogen,
A compound according to claim 2. 4. A compound according to claim 2, wherein both R ¹ and R ² are chloro. 5. A compound according to claim 3, wherein X, Y and Z have no more than 3 carbon atoms. 6. A compound according to claim 4, wherein X, Y and Z have no more than 3 carbon atoms. 7 Two of X, Y and Z represent a C ₁ -C ₃ alkyl group, and both of these groups are 5 of the 1,3-dioxane nucleus.
- The compound according to claim 5, which is bonded at the - position. 8 Two of X, Y and Z represent a C ₁ to C ₃ alkyl group, and both of these groups are 5 of the 1,3-dioxane nucleus.
7. A compound according to claim 6, which is attached at the - position. 9 1-[2-(2,4-dichlorophenyl)-5
-ethyl-methyl-1,3-dioxan-2-ylmethyl]-1H-1,2,4-triazole and its pharmaceutically acceptable acid addition salts, metal salt complexes and stereochemically isomeric forms. A compound according to claim 1. 10 1-[2-(2,4-dichlorophenyl)-
From the group consisting of 5,5-diethyl-1,3-dioxan-2-ylmethyl]-1H-1,2,4-triazole and its pharmaceutically acceptable acid addition salts, metal salt complexes and stereochemically isomeric forms A compound according to selected claim 1. 11 1-[2-(2,4-dichlorophenyl)-
5,5-dimethyl-1,3-dioxan-2-ylmethyl]-1H-1,2,4-triazole and its pharmaceutically acceptable acid addition salts, metal salt complexes and stereochemically isomeric forms; A compound according to selected claim 1. 12 1-[2-(2,4-dichlorophenyl)-
5-Methyl-5-propyl-1,3-dioxan-2-ylmethyl]-1H-1,2,4-triazole and its pharmaceutically acceptable acid addition salts, metal salt complexes and stereochemically isomeric forms. A compound according to claim 1 selected from the group. 13 1-[2-(2,4-dichlorophenyl)-
4-methyl-1,3-dioxan-2-ylmethyl]-1H-1,2,4-triazole and its pharmaceutically acceptable acid addition salts, metal salt complexes and stereochemically isomeric forms. A compound according to claim 1. 14 1-[2-(2,4-dichlorophenyl)-
4,6-dimethyl-1,3-dioxan-2-ylmethyl]-1H-1,2,4-triazole and its pharmaceutically acceptable acid addition salts, metal salt complexes and stereochemically isomeric forms; A compound according to selected claim 1. 15 formula In the formula, R ¹ and R ² are each independently selected from the group consisting of hydrogen and halogen, and the conditions are that R ¹ and R ²
Q is a member selected from the group consisting of CH and N; X, Y and Z are each independently selected from the group consisting of hydrogen and C ₁ -C ₄ alkyl; , the conditions are X, Y
and at least one of Z is other than hydrogen, and compounds selected from the group consisting of azole derivatives thereof, and their pharmaceutically acceptable acid addition salts, metal salt complexes, and stereochemically isomeric forms for plants. A disinfectant characterized by containing as an active ingredient. 16 R ¹ is hydrogen, chloro or bromo,
16. A preparation according to claim 15, wherein ^R2 is chloro or bromo. 17. The agent according to claim 16, wherein R ² is chloro and R ¹ is hydrogen. 18. The agent according to claim 16, wherein both R ¹ and R ² are chloro. 19. The agent of claim 17, wherein none of X, Y and Z have more than 3 carbon atoms. 20. The agent of claim 18, wherein none of X, Y and Z have more than 3 carbon atoms. 21 Two of X, Y and Z represent _C1 - _C3 alkyl groups, both of which are bonded to the 5-position of the 1,3-dioxane nucleus, Claim 19
Agents listed in section. 22 Two of X, Y and Z represent _C1 - _C3 alkyl groups, both of which are bonded to the 5-position of the 1,3-dioxane nucleus, Claim 20
Agents listed in section. 23 As an active ingredient, 1-[2-(2,4-dichlorophenyl)-5,5-diethyl-1,3-sioxan-2-ylmethyl]-1H-1,2,4-
16. The agent according to claim 15, comprising a compound selected from the group consisting of triazole and its pharmaceutically acceptable acid addition salts, metal salt complexes, and stereochemical isomers. 24 As an active ingredient, 1-[2-(2,4-dichlorophenyl)-5,5-dimethyl-1,3-dioxan-2-ylmethyl]-1H-1,2,4-
16. The agent according to claim 15, comprising a compound selected from the group consisting of triazole and its pharmaceutically acceptable acid addition salts, metal salt complexes and stereochemically isomeric forms. 25 As an active ingredient, 1-[2-(2,4-dichlorophenyl)-5-methyl-5-propyl-1,
3-dioxan-2-ylmethyl]-1H-1,
16. The agent according to claim 15, comprising a compound selected from the group consisting of 2,4-triazole and its manufacture-acceptable acid addition salts, metal salt complexes and stereochemically isomeric forms. 26 As an active ingredient, 1-[2-(2,4-dichlorophenyl)-4-methyl-1,3-dioxan-2-ylmethyl]-1H-1,2,4-triazole and its pharmaceutically acceptable Claim 15 comprising a compound selected from the group consisting of acid addition salts, metal salt complexes and stereochemically isomeric forms obtained
Agents listed in section. 27 As an active ingredient, 1-[2-(2,4-dichlorophenyl)-4,6-dimethyl-1,3-dioxan-2-ylmethyl]-1H-1,2,4-
16. The agent according to claim 15, comprising a compound selected from the group consisting of triazole and its pharmaceutically acceptable acid addition salts, metal salt complexes and stereochemically isomeric forms. 28 formula In the formula, R ¹ and R ² are each independently selected from the group consisting of hydrogen and halogen, and the conditions are that R ¹ and R ²
Q is a member selected from the group consisting of CH and N; X, Y and Z are each independently selected from the group consisting of hydrogen and C ₁ -C ₄ alkyl; , the conditions are X, Y
and 1-(2-aryl-1,3-dioxan-2-ylmethyl)-1H-imidazole and at least one of Z is other than hydrogen.
In preparing compounds selected from the group consisting of 1H-1,2,4-triazole derivatives and their pharmaceutically acceptable acid addition salts, metal salt complexes and stereochemical isomers, the formula where Q is as defined above, and
Me is hydrogen, 4-substituted ammonium ion,
is a tri-( _C1 - _C6 -alkyl)ammonium or metal atom, and is a compound with the formula wherein R ¹ , R ² , X, Y and Z are as defined above and T is halogen, wherein the compounds of formulas () and () are If the reaction is relatively polar and is carried out in an inert organic solvent at elevated temperature, and M represents hydrogen, the reaction is carried out in the presence of a base and optionally the product is 1-(2-aryl-
1,3-Dioxan-2-ylmethyl)-1H-imidazole and 1H-1,2,4-triazole derivatives and their pharmaceutically acceptable acid addition salts, metal salt complexes and stereochemically isomeric forms for plants. Methods for producing selected compounds.