CH653024A5 - 1,2,4-TRIAZOL-1-YL-PROPIONITRILE, METHOD FOR PRODUCING THESE COMPOUNDS AND THE BIOCIDES CONTAINING THEM. - Google Patents

Description

The invention relates to new 1,2,4-triazol-l-yl-propionitrile processes for the preparation of these compounds and to biocidal compositions containing them, in particular with a fungicidal action.

Imidazolyl-propionitrile derivatives with fungicidal activity are already known (DE-OS 2 604 047). However, these have a relatively narrow spectrum of activity, which is unsatisfactory.

The object of the present invention is to develop new propionitrile derivatives which open up a wide range of possible uses, in particular in the field of crop protection, and which have a broad spectrum of fungicidal activity.

653024

This object is achieved according to the invention by imidazolylpropionitriles of the general formula

R-C-CH2-N (I)

I \ = N

CN

in the

R is an aromatic hydrocarbon radical optionally substituted one or more times, identically or differently, by halogen, (Ci-GO-alkyl, (Ci-C4) alkoxy, (Ci-GO-alkylthio, trifluoromethyl or the nitro group) and Ri (Ci-Cio) -Alkyl, (C3-Cs) -alkenyl, (C3-Cs) -alkynyl or one optionally one or more times, identically or differently by halogen, (Ci-C4) -alkyl, (Ci-C4) -alkoxy, (Ci -C4) -Alkylthio, trifluoromethyl or the nitro group substituted phenylalkyl radical, and their acid addition salts with inorganic and organic acids.

The compounds according to the invention are biocidally active in the broadest sense, but are particularly notable for a fungicidal action, in which they surprisingly outperform known active substances of analogous constitution and direction of action.

The fungicidal action surprisingly extends against fungi of various systematic positions. When treating above-ground parts of plants, they protect against wind-borne pathogens. The compounds can be used to treat seed-borne pathogens. In addition, these act systematically, that is, they are absorbed by the roots of the plants, for example after being introduced into the seed, are transported to the aerial parts of the plant and protect them against pathogens.

Further effects include a growth regulatory and a bactericidal effect.

Because of the recognized broad spectrum of activity, the compounds are not only suitable for protecting crop plants, but also for protecting materials and combating human-pathogenic and animal-pathogenic microbes, which results in a wide range of possible uses.

Depending on the special meaning of the substituents, there are focal areas of application in which the compounds have outstanding effects. So they can be used as fungicides, plant growth regulators or bactericides.

In the compounds drawn by the general formula I can mean, for example:

R 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2-bromophenyl,

3-bromophenyl, 4-bromophenyl, 2-iodophenyl, 3-iodophenyl,

4-iodophenyl, 2,4-dichlorophenyl, 3,4-dichlorophenyl, 2,6-dichlorophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 4-ethylphenyl,

2-propylphenyl, 3-propylphenyl, 4-propylphenyl, 2-isopropylphenyl, 3-isopropylphenyl, 4-isopropylphenyl, 2-butylphenyl, 3-butylphenyl, 4-butylphenyl, 2-sec-butylphenyl,

3-sec-butylphenyl, 4-sec-butylphenyl, 2-tert-butylphenyl, 3-tert-butylphenyl, 4-tert-butylphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2-ethoxyphenyl , 3-ethoxyphenyl, 4-ethoxyphenyl, 2-methylthiophenyl, 3-methylthiophenyl, 4-methylthiophenyl, 2-ethylthiophenyl, 3-ethylthiophenyl, 4-ethylthiophenyl, 2-trifluoromethylphenyl, 3-trifhiormethylphenyl, 4-trifluoromethylphenyl , 2-nitrophenyl, 3-nitrophenyl, 4-nitrophenyl,

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3-fluoro-4-methoxyphenyl, 3-chloro-5-nitrophenyl, 4-chloro

2-fluorophenyl, 3,4,5-trimethoxyphenyl, or 2-chloro-2-nitrophenyl and

Ri (Ci-Cio) alkyl, for example methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, isopropyl, 2,2-dimethylpropyl-l, 3,3-dimethyl-butyl-2 , (C3-C8) alkenyl, for example 2-buten-1-yl, 3-methyl-2-buten-1-yl, hexenyl, heptenyl, octenyl, phenylalkyl which may be substituted according to claim 1, for example benzyl, 2- Fluorobenzyl, 3-fluorobenzyl, 4-fluorobenzyl, 2-chlorobenzyl,

3-chlorobenzyl, 4-chlorobenzyl, 2-bromobenzyl, 3-bromobenzyl, 4-bromobenzyl, 2,4-dichlorobenzyl, 2,6-dichlorobenzyl, 3,4-dichlorobenzyl, 2-methylbenzyl, 3-methylbenzyl,

4-methylbenzyl, 2-nitrobenzyl, 3-nitrobenzyl, 4-nitrobenzyl, 2-trifluoromethylbenzyl, 3-trifluoromethylbenzyl, 4-trifluoromethylbenzyl, 2-methoxybenzyl, 3-methoxybenzyl, 4-methoxybenzyl, 2-ethoxybenzyl Ethoxybenzyl, 4-ethoxybenzyl, 2-propoxybenzyl, 3-propoxybenzyl, 4-propoxybenzyl, 2-butoxybenzyl, 3-butoxybenzyl, 4-butoxy-benzyl, 2-methylthiobenzyl, 3-methylthiobenzyl, 4-methylthiobenzyl, 2- Ethylthiobenzyl, 3-ethylthiobenzyl, 4-ethylthiobenzyl, 2-butylthiobenzyl, 3-butylthiobenzyl, 4-butylthiobenzyl.

Examples of inorganic and organic acids to form the acid addition salts include hydrohalic acid, such as hydrochloric acid and hydrobromic acid, phosphoric acid, sulfuric acid, especially nitric acid, mono- and bifunctional carboxylic acids and hydroxycarboxylic acids, such as acetic acid, maleic acid, succinic acid , Fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid, lactic acid, and sulfonic acids, such as p-toluenesulfonic acid and 1,5-naphthalenedisulfonic acid.

These acid addition salts can be obtained by the usual salt formation methods, for example by dissolving a compound of formula I in a suitable solvent and adding the acid.

Of the compounds according to the invention are notable for a fungicidal action, in particular those in which the radical R in the general formula I is phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 3,4-dichlorophenyl, 4-Bromophenyl, 2-fluorophenyl, 4-fluorophenyl or 2-methylphenyl and R 1 mean ethyl, allyl, propyl, isopropyl, butyl or hexyl.

Of these, preference should be given to compounds in which

R represents phenyl, 4-chlorophenyl or 2-methylphenyl and Ri propyl, isopropyl or butyl.

The following compounds according to the invention are of outstanding activity:

2-isopropoxy-2-phenyl-3- (1,2,4-triazol-1-yl) propionitrile, hydronitrate

2-butoxy-2- (2-methylphenyl) -3- (1,2,4-triazol-l-yl) propionitrile, hydronitrate

2-phenyl-2-propoxy-3- (1,2,4-triazol-1-yl) propionitrile, hydronitrate

2-butoxy-2- (4-chlorophenyl) -3- (1,2,4-triazol-l-yl) propionitrile, hydronitrate

2- (4-chlorophenyl) -2-propoxy-3- (1,2,4-triazol-1-yl) propionitrile, hydronitrate

2-isopropoxy-2-phenyl-3- (l, 2,4-triazol-l-yl) propionitrile 2-butoxy-2- (2-methylphenyl) -3- (1,2,4-triazol-1 - yl) -propioni-tril

2-hexyloxy-2-phenyl-3 - (1,2,4-triazol-1-yl) propionitrile, hydronitrate

2-butoxy-2- (4-chlorophenyl) -3- (1,2,4-triazol-l-yl) propionitrile

2- (4-chlorophenyl) -2-propyloxy-3- (1,2,4-triazol-1-yl) propionitrile

2-Hexyloxy-2- (2-methylphenyl) -3- (1,2,4-triazol-1-yl) propionitrile, hydronitrate

2-butoxy-2-phenyl-3- (1,2,4-triazol-1-yl) propionitrile, hydronitrate

2-butoxy-2- (2-chlorophenyl) -3- (1,2,4-triazol-1-yl) propionitrile, hydronitrate

2-ethoxy-2-phenyl-3- (l, 2,4-triazol-l-yl) propionitrile, hydronitrate

2-allyloxy-2-phenyl-3- (1,2,4-triazol-1-yl) propionitrile, hydronitrate

2- (2-chlorophenyl) -2-propoxy-3 - (1,2,4-triazol-1-yl) propionitrile, hydronitrate

2- (4-chlorophenyl) -2-hexyloxy-3- (l, 2,4-triazol-l-yl) propionitrile, hydronitrate

2-Hexyloxy-2- (2-methylphenyl) -3- (1,2,4-triazol-l-yl) propionitrile

2-butoxy-2-phenyl-3- (1,2,4-triazol-1-yl) propionitrile

2- (2-chlorophenyl) -2-butoxy-3- (l, 2,4-triazol-l-yl) propioni-

tril

2-ethoxy-2-phenyl-3- (1,2,4-triazol-1-yl) propionitrile 2-allyloxy-2-phenyl-3- (1,2,4-triazol-l-yl) propionitrile 2- (2-chlorophenyl) -2-propoxy-3- (1,2,4-triazol-l-yl) propionitrile

The compounds according to the invention in particular show fungicidal effects, but are also notable for growth-regulating effects in a number of crop plants.

Depending on the type of plant and the application rate, herbicidal effects also result.

Since the compounds according to the invention cause both qualitative and quantitative changes in plants and also changes in the metabolism of the plants, they are to be classified in the class of plant growth regulators which are distinguished by the following possible uses:

Inhibition of vegetative growth in woody and herbaceous plants, for example on the side of roads, track systems, etc., to prevent abundant growth. Growth inhibition in cereals to prevent storage or twisting, in cotton to increase yield.

Influencing the branching of vegetative and generative organs in ornamental or cultivated plants to increase the flower set or in tobacco and tomato to inhibit side shoots.

Improvement in fruit quality, for example an increase in the sugar content of sugar cane, sugar beet or fruit, and more uniform ripening of the crop, which leads to higher yields.

Increased resistance to climatic influences such as cold and drought.

Influencing the latex flow in rubber plants. Education of parthenocarpic fruits, pollen sterility and gender interference are also possible applications:

Control the germination of seeds or buds.

Defoliation or influencing of the crop fall to facilitate harvesting.

The compounds according to the invention are particularly suitable

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especially for influencing the growth of beta beets, but also show the desired growth-regulating effects for cereals, soybeans and cotton.

Depending on the intended use, the application rates are generally from 0.05 to 5 kg of active ingredient / ha, if appropriate higher application rates can also be used.

The application time depends on the application goal and the climatic conditions.

Surprisingly, the compounds according to the invention are broader or more effective than products of the same direction of action which are known in practice.

In addition to the above-mentioned effects, the compounds according to the invention also have a bactericidal action which permits further possible uses.

The compounds according to the invention can be used either alone, in a mixture with one another or with other active ingredients. If necessary, other pesticides or pesticides can be added depending on the desired purpose.

The labeled active ingredients or their mixtures are expediently in the form of preparations, such as powders, sprinkling agents, granules, solutions, emulsions or suspensions, with the addition of liquid and / or solid carriers, or diluents and, if appropriate, wetting agents, adhesives, emulsifiers and / or dispersing aids applied.

Suitable liquid carriers are, for example, water, aliphatic and aromatic hydrocarbons, such as benzene, toluene, xylene, cyclohexanone, isophorone, dimethyl sulfoxide, dimethylformamide, mineral oil fractions and vegetable oils.

Mineral soils are particularly suitable as solid carriers, for example tonsil, silica gel, talc, kaolin, attapulgite, limestone, silica and vegetable products, for example flours.

Preferred surface-active substances include: for example calcium lignin sulfonate, polyoxyethylene alkylphenyl ether, naphthalene sulfonic acids and their salts, formaldehyde condensates, fatty alcohol sulfates and substituted benzenesulfonic acids and their salts.

If the active ingredients are to be used for seed dressing, dyes can also be added in order to give the seed dressing a clearly visible color.

The proportion of the active ingredient (s) in the various preparations can vary within wide limits. For example, the agents contain about 10 to 90 percent by weight of active ingredients, about 90 to 10 percent by weight of liquid or solid carriers and optionally up to 20 percent by weight of surface-active agents.

The agents can be applied in a customary manner, for example using water as a carrier in spray liquor amounts of about 100 to 1000 liters / ha. Application of the agents in the so-called “low-volume” or “ultra-low-volume method” is just as possible as their application in the form of so-called microgranules.

For example, the following ingredients are used to prepare the preparations:

A. wettable powder a) 40% by weight of active ingredient

25% by weight of clay minerals

20% by weight of silica

10% by weight cell pitch

5% by weight of surfactants based on a

Mixing the calcium salt of lignin sulfonic acid with

Alkylphenol polyglycol ethers b) 25% by weight of active ingredient

60% by weight kaolin 10% by weight silica

5% by weight of surface-active substances based on the sodium salt of N-methyl-N-oleyl-taurine and the calcium salt of lignin sulfonic acid c) 10% by weight of active ingredient 60% by weight of clay minerals 15% by weight of silica

10% by weight cell pitch

5% by weight of surface-active substances based on the sodium salt of N-methyl-N-oleyl-taurine and the calcium salt of lignin sulfonic acid

B. Paste

45% by weight of active ingredient 5% by weight of sodium aluminum silicate 15% by weight of cetyl polyglycol ether with 8 mol of ethylene oxide 2% by weight of spindle oil 10% by weight of polyethylene glycol 23 parts of water

C. Emulsion concentrate 25% by weight of active ingredient

15% by weight cyclohexanone 55% by weight xylene 5% by weight mixture of nonylphenylpolyoxyethylene or calcium dodecylbenzenesulfonate.

The new compounds according to the invention are prepared by propionitriles of the general formula

O-Ri

I.

R C-CH2-Y (II)

I.

CN

with 1,2,4-triazole of the formula N-CH

11 II

HC N

H

or its alkali compounds in the presence of a solvent, if appropriate in the presence of a base, in which Rund Ri have the meaning given above and Y is halogen, or the alkylsulfonyloxy or arylsulfonyloxy radical which may be halogenated in the side chain.

Halogen is, for example, chlorine, bromine or iodine; Suitable alkylsulfonyloxy radicals are, for example, methyl, ethyl, propyl and the trifluoromethylsulfonyloxy group, and arylsulfonyloxy radicals which may be mentioned include the benzylsulfonyloxy and p-toluenesulfonyloxy groups.

The reaction can be carried out either with an excess of 1,2,4-triazole or with the addition of a strong base, for example sodium or potassium hydroxide. In addition, 1,2,4-triazole alkali metal can also be used instead of 1,2,4-triazole.

Suitable solvents which are inert toward the reactants are preferably polar, aprotic in character, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, tetramethylurea, hexamethylphosphoric triamide and benzonitrile, but also s

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higher-boiling aromatic and aliphatic hydrocarbons such as toluene, chlorobenzene or xylene.

The reaction temperature can be varied within wide limits. A temperature between 100 ° C. and 200 ° C. is preferred. The implementations take place under normal or overpressure.

The 1,2,4-triazol-l-yl-propionitriles according to the invention are generally almost colorless and odorless solids. The acid addition salts derived therefrom are also colorless and odorless, crystalline compounds. The free bases dissolve poorly in water and more or less well in organic solvents such as alcohols, ethers or chlorinated hydrocarbons. The acid addition salts partly dissolve in water and well in polar organic solvents such as acetonitrile, N, N-dimethylformamide, lower alcohols, chloroform and methylene chloride.

The following examples illustrate the preparation of the compounds according to the invention.

example 1

2-isopropoxy-2-phenyl-3- (l, 2,4-triazol-l-yl) propionitrile hydronitrate Compound No. 2

0.55 mol of 1,2,4-triazole is added to sodium hydride (0.55 mol) suspended in 50 ml of dry DMF with stirring and cooling. Then 0.11 mol of 2-isopropoxy-3-methyl-sulfonyloxy-2-phenyl-propionitrile in 50 ml of DMF are added and the mixture is kept at a bath temperature of 150 ° C. for 1.5 hours. After cooling, the mixture is extracted 3 times with 100 ml of ether, the combined ether phases are washed twice with water and dried with MgSOt. The ether is rotated in a vacuum, 50 ml of isopropanol are added to the residue and 6.8 ml of concentrated nitric acid are added dropwise with cooling. with stirring. After adding 80 ml of ether, the mixture is stirred for a further hour and then suction filtered. It is recrystallized from isopropanol.

OK mp: 185-189 ° C (decomposition)

Yield: 15 g = 43% of theory DMF = dimethylformamide

Example 2

Is 2-isopropoxy-2-phenyl-3- (1,2,4-triazol-l-yl) propionitrile Compound No. 3

10 g of 2-isopropoxy-2-phenyI-3- (l, 2,4-triazol-l-yl) propionitrile, hydronitrate are dissolved in methanol and 8 ml of 32% ammonia water are added. You give on water

20 extracted with ethyl acetate, dried over MgSCU, rotated the ethyl acetate in vacuo, mixed with a little ethyl acetate and activated carbon, boiled briefly, sucked off and rotated again. The resulting solid is pure for analysis.

25 mp: 176-177 ° C

Yield: 6.65 g = 83% of theory

The following compounds according to the invention can be prepared in an analogous manner.

No. Name of the connection Physical constant

1. 2-hexyloxy-2- (2-methylphenyl) -3- (l, 2,4-triazol-l-yl) propionitrile, hydronitrate mp: 159-62 ° C (Z)

4. 2-Butoxy-2- (2-methylphenyl) -3- (1,2,4-triazol-l-yl) propionitrile, mp: 58-62 ° C

5. 2-butoxy-2- (2-methylphenyl) -3- (l, 2,4-triazol-l-yl) propionitrile, hydronitrate mp: 158-61 ° C (Z)

6. 2-Hexyloxy-2- (2-methylphenyl) -3- (1,2,4-triazol-l-yl) propionitrile n 0: 1.5121

7. 2-Butoxy-2-phenyl-3- (l, 2,4-triazol-l-yl) propionitrile, hydronitrate mp: 159-60 ° C (Z)

8. 2-butoxy-2- (2-chlorophenyl) -3- (l, 2,4-triazol-l-yl) propionitrile, hydronitrate mp: 142.5-44 ° C (Z)

9. 2-ethoxy-2-phenyl-3- (1,2,4-triazol-l-yl) propionitrile, hydronitrate mp: 169-70 ° C (Z)

10. 2-phenyl-2-propoxy-3- (l, 2,4-triazol-l-yl) propionitrile, hydronitrate mp: 178-79 ° C (Z)

11. 2- (3-chlorophenyl) -2-hexyloxy-3- (l, 2,4-triazol-l-yl) propionitrile, hydronitrate mp: 173-75 ° C (Z)

12. 2-Butoxy-2-phenyl-3- (l, 2,4-triazol-l-yl) propionitrile mp: 67-68 ° C

13. 2-phenyl-2-propoxy-3- (l, 2,4-triazol-l-yl) propionitrile m.p .: 107-08 ° C

14. 2-ethoxy-2-phenyl-3- (l, 2,4-triazol-l-yl) propionitrile mp: 74-75 ° C

15. 2-Hexyloxy-2-phenyl-3- (l, 2,4-triazol-l-yl) propionitrile, hydronitrate mp: 158-60 ° C (Z)

16. 2-allyloxy-2-phenyl-3- (l, 2,4-triazol-l-yl) propionitrile, hydronitrate mp: 145-47 ° C. (Z)

17. 2-Butoxy-2- (4-chlorophenyl) -3- (l, 2,4-triazol-l-yl) propionitrile, hydronitrate, mp: 173-75 ° C (Z)

18. 2-Allyloxy-2-phenyl-3- (l, 2,4-triazol-l-yl) propionitrile mp: 86-88 ° C

19. 2-methoxy-2-phenyl-3- (l, 2,4-triazol-l-yl) propionitrile mp: 77-79 ° C

20. 2-Hexyloxy-2-phenyl-3- (l, 2,4-triazol-l-yl) propionitrile mp: 58-60 ° C

21. 2- (2-chlorophenyl) -2-hexyloxy-3- (l, 2,4-triazol-l-yl) propionitrile, hydronitrate mp: 157-59 ° C (Z)

22. 2- (2-chlorophenyl) -2-propoxy-3- (l, 2,4-triazol-l-yl) propionitrile, hydronitrate mp: 138-39 ° C (Z)

23. 2- (4-chlorophenyl) -2-propoxy-3- (l, 2,4-triazol-l-yl) propionitrile, hydronitrate mp: 155-57 ° C (Z)

24. 2- (4-chlorophenyl) -2-hexyloxy-3- (l, 2,4-triazol-l-yl) propionitrile, hydronitrate mp: 155-59 ° C (Z)

25. 2- (4-chlorophenyl) -2-propyloxy-3- (l, 2,4-triazol-l-yl) propionitrile mp: 115-19 ° C

26. 2-Butoxy-2- (4-chlorophenyl) -3- (1,2,4-triazol-l-yl) propionitrile, mp: 54-60 ° C

27. 2- (2-methylphenyl) -2-octyloxy-3- (l, 2,4-triazol-l-yl) propionitrile, hydronitrate mp: 128-34 ° C (Z)

28. 2-decyloxy-2- (2-methylphenyl) -3- (l, 2,4-triazol-l-yl) propionitrile, hydronitrate mp: 116-20 ° C (Z)

29. 2- (2-methylphenyl) -2-octyloxy-3- (1,2,4-triazol-l-yl) propionitrile n0: 1.4930

30. 2- (2-chlorophenyl) -2-butoxy-3- (1,2,4-triazol-l-yI) propionitrile n0: 1.5273

31. 2- (2-chlorophenyl) -2-propoxy-3- (l, 2,4-triazol-l-yl) propionitrile n ° 0: 1.5308

32. 2-Butoxy-2- (2,4-dichlorophenyl) -3- (l, 2,4-triazol-l-yl) propionitrile, hydronitrate, mp: 163-66 ° C

33. 2-Butoxy-2- (2,4-dichlorophenyl) -3- (l, 2,4-triazol-l-yl) propionitrile mp: 53-55 ° C

34. 2-Allyloxy-2- (2,4-dichlorophenyl) -3- (1,2,4-triazol-l-yl) propionitrile, mp: 104-07 ° C

35. 2- (3,4-dichlorophenyl) -2-propoxy-3- (l, 2,4-triazol-l-yl) propionitrile, hydronitrate, mp: 152-55 ° C (Z)

36. 2- (3,4-dichlorophenyl) -2-propoxy-3- (l, 2,4-triazol-l-yl) propionitrile mp: 60-66 ° C

37. 2- (3,4-dichlorophenyl) -2-hexyloxy-3- (l, 2,4-triazol-l-yl) propionitrile, hydronitrate, mp: 166-68 ° C

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No.

Name of the connection

Physical constant

38.

2- (3,4-dichlorophenyl) -2-hexyloxy-3- (l, 2,4-triazol-l-yl) propionitrile n4D0: 1.5240

39.

2- (4-fluorophenyl) -2-propoxy-3- (1,2,4-triazol-l-yl) propionitrile, hydronitrate

Mp

: 172-75 ° C (Z)

40.

2- (4-fluorophenyl) -2-propoxy-3- (1,2,4-triazol-1-yl) propionitrile

Fp .:

: 98-100 ° C

41.

2-butoxy-2- (4-fluorophenyl) -3- (1,2,4-triazol-l-yl) propionitrile, hydronitrate

Fp .:

: 173-75 ° C (Z)

42.

2-butoxy-2- (4-fluorophenyl) -3- (1,2,4-triazol-l-yl) propionitrile

Fp .:

: 56-58 ° C

43.

2- (2-fluorophenyl) -2-propoxy-3- (1,2,4-triazol-l-yl) propionitrile, hydronitrate

Mp

: 150-53 ° C (Z)

44.

2- (2-fluorophenyl) -2-propoxy-3- (1,2,4-triazol-l-yl) propionitrile

Fp .:

: 66-69 ° C

45.

2-butoxy-2- (2-fluorophenyl) -3- (1,2,4-triazol-l-yl) propionitrile, hydronitrate

Fp .:

: 138-43 ° C (Z)

46.

2-butoxy-2- (2-fluorophenyl) -3- (1,2,4-triazol-l-yl) propionitrile

Fp .:

: 76-79 ° C

47.

2- (2-fluorophenyl) -2-hexyloxy-3- (1,2,4-triazol-1-yl) propionitrile, hydronitrate

Fp .:

: 134-37 ° C (Z)

48.

2- (2-fluorophenyl) -2-hexyloxy-3- (1,2,4-triazol-l-yl) propionitrile

Fp .:

: 58-60 ° C

49.

2- (4-bromophenyl) -2-propoxy-3- (1,2,4-triazol-l-yl) propionitrile, hydronitrate

Fp .:

: 150-53 ° C (Z)

50.

2- (4-bromophenyl) -2-propoxy-3- (1,2,4-triazol-l-yl) propionitrile

Fp .:

: 118-21 ° C

51.

2- (4-bromophenyl) -2-hexyloxy-3- (1,2,4-triazol-l-yl) propionitrile, hydronitrate

Fp .:

: 161-64 ° C (Z)

52.

2- (4-bromophenyl) -2-hexyloxy-3- (1,2,4-triazol-1-yl) propionitrile

Fp .:

: 60-62 ° C

53.

2- (2,4-dichlorophenyl) -2-propoxy-3- (l, 2,4-triazol-l-yl) propionitrile, hydronitrate

Fp .:

: 166-70 ° C (Z)

54.

2- (2,4-dichlorophenyl) -2-propoxy-3- (1,2,4-triazole) propionitrile

Fp .:

: 61-63 ° C

55.

2- (2-methylphenyl) -2-pentoxy-3- (1,2,4-triazol-l-yl) propionitrile, hydronitrate

Fp .:

: 151-54 ° C (Z)

56.

2- (2-methylphenyl) -2-pentoxy-3- (1,2,4-triazol-1-yl) propionitrile n ° 0: 1.5111

57.

2- (4-methylphenyl) -2-propoxy-3- (1,2,4-triazol-l-yl) propionitrile, hydronitrate

Fp .:

: 170-71 ° C (Z)

58.

2-Hexyloxy-2- (4-methylphenyl) -3- (1,2,4-triazol-l-yl) propionitrile, hydronitrate

Fp .:

177-81 ° C (Z)

59.

2- (4-methylphenyl) -2-propoxy-3- (1,2,4-triazol-1-yl) propionitrile

Fp .:

: 120-24 ° C

60.

2-Hexyloxy-2- (4-methylphenyl) -3- (1,2,4-triazol-l-yl) propionitrile n0: 1.5065

61.

2-butoxy-2- (4-methylphenyl) -3- (1,2,4-triazol-l-yl) propionitrile

Fp .:

71-73 ° C

Z - decomposition

The 3-aryl or. 3-alkylsulfonyloxy-propionitriles of the general formula II with Y meaning aryl- or alkylsulfonyloxy have not hitherto been described in the literature.

They are obtained by using the methods which are known or known per se (cf. for example Rubin et al., JACS 67,192 f [1945]; Hess et al., Ber. Dt. Formerly Ges. 50,394 [1917]) accessible phenylacetonitriles of the general formula III

O-Ri

I.

R-CH III

I.

CN

where R and Ri have the meaning given for formula I, hydroxymethylated by methods known per se and the 3-hydroxypropionitriles of the general formula IV thus obtained

O-Ri

R-C-CH2-OH IV

I.

CN

with suitable sulfonic acid derivatives, such as sulfonic acid chlorides, optionally with the addition of an acid binder. The hydroxymethyl compounds of the general formula IV are not yet known from the literature.

The production of a starting product is described below.

3-methylsulfonyl-2-phenyl-2-propoxy-propionitrile 27 g (0.154 mol) of 2-phenyl-2-propoxy-acetonitrile are dissolved in 120 ml of pyridine and mixed with 18.5 g (0.614 mol) of paraformaldehyde. 7.7 ml of tetrabutylammonium hydroxide (TBAOH) as a 40% solution are added to this suspension with ice cooling and the mixture is stirred vigorously. After a few hours (DC control), pour on ice water and extract with ether. The ether phase is washed with dilute hydrochloric acid and then with sodium chloride solution and dried with magnesium sulfate. After filtering off the desiccant and spinning in a vacuum, a colorless oil remains, which proves to be uniform by thin layer chromatography and can be processed 40 without further purification.

Yield: 28.4 g = 90% of theory 3-hydroxy-2-phenyl-2-propoxypropionitrile n ^ 0: 1.5027.

28 g (0.136 mol) of 3-hydroxy-2-phenyl-2-propoxypropionitrile are dissolved in 200 ml of toluene, and 19.5 g (0.171 45 mol) of methanesulfonic acid chloride are added.

18.6 g (0.184 mol) of triethylamine are added dropwise at 10 ° C. The mixture is stirred at room temperature for 30 minutes, filtered from the precipitated triethylamine hydrochloride and concentrated. The residue is taken up in ether, washed with water, dried over magnesium sulfate and concentrated. The oily residue proves to be pure by thin layer chromatography.

Yield: 32.27 g = 86% of theory 3-methylsulfonyl-2-phenyl-2-propoxypropionitrile n ^ 0: 1.5000.

The following exemplary embodiments serve to explain the possible uses of the compounds according to the invention, which took place in the form of the preparations mentioned above.

Example 3

60 Effect of prophylactic leaf treatment against powdery mildew Erysiphe graminis on barley in the greenhouse.

Young barley plants in the stage of the first leaf were sprayed to runoff point at the concentrations indicated. After the spray coating had dried on, the 65 treated plants and untreated control plants were inoculated with dry powdery pores by coating the test plants with infected plants. The test plants were then grown in the greenhouse at about 20

653 024

8th

cultivated up to 22 ° C and rated for one percent attack on the leaf surface after one week. The fungicidal activity was calculated as follows:

100

Infested in Treated-100

=% Effect

Infection in untreated The compounds were in the form of 20% formulations.

siphe cichoracearum on pumpkin plants in a greenhouse

Pumpkin plants sprayed to runoff point with the specified active ingredient concentrations were inoculated after the spray coating had dried on by dusting dry flour spores of Erysiphe cichoracearum and incubated together with inoculated, untreated control plants in the greenhouse at 24 ° C. After one week, the infected flour surface was estimated in% of the total leaf area. The fungicidal activity was calculated as follows:

Compound No. according to the invention

Erysiphe graminis% effect 500 ppm

100 ppm

1

100

95

2nd

100

59

3rd

100

100

4th

100

100

5

100

95

6

100

94

7

100

100

8th

100

100

9

100

100

10th

100

100

11

100

94

12

100

100

13

100

100

14

100

100

15

100

100

16

100

100

17th

100

100

18th

100

100

19th

100

100

20th

100

100

21st

100

95

22

100

100

23

100

100

24th

100

-

25th

100

-

26

100

-

28

100

95

30th

100

100

31

100

100

33

100

100

34

100

100

35

100

100

36

100

100

38

100

100

41

100

100

42

100

100

44

100

100

48

100

95

49

100

100

50

100

100

51

100

100

52

100

100

53

100

100

54

100

100

55

100

100

57

100

100

58

100

100

59

100

100

60

100

100

61

100

100

10th

100-

Infestation in Treated-100 Infestation in Untreated

=% Effect

15

The note “s” in the table below means that the fungicidal activity was also assessed by the growth of the plants (after the treatment) and was found to be positive. This means that the active ingredients were systemically transported in growth and also had 100% action against mildew on 20 of these.

The compounds according to the invention were in the form of 20% formulations.

25th

30th

35

40

45

50.

Compounds No.

Erysiphe cichoracearum% effect 250 25 5 2.5 0.5 ppm

1

100s

100s

100s

2nd

100s

100s

100s

3rd

100s

100s

100s

4th

100s

100s

100

5

100s

100s

100

6

100s

100s

100

7

100

100

100

8th

100s

98

100

9

100s

100s

100s

10th

100s

100s

100

11

100s

100s

100

12

100s

100s

100

13

100s

14

100s

100s

100

15

100s

100

100

16

100s

100

99.5

17th

100s

100s

100s

18th

100s

100s

100

19th

100s

100

97

20th

100s

21st

100s

100

90

22

100s

100

100

55

Compounds according to the invention Erysiphe cichoracearum% action no.

250

Example 4

Effect of prophylactic leaf treatment against ery-

27th

100s

29

100s

32

100s

37

100s

39

100s

40

100s

43

100s

45

100s

46

100s

47

100s

56

100s

9

653024

Example 5

Effect (%) of prophylactic leaf treatment against Helminthosporium teres (= Pyrenophora teres), barley mesh spot disease

Young barley plants in the stage of the first leaf were sprayed to runoff point at the concentrations indicated. After the spray coatings had dried on, the treated plants and untreated control plants were sprayed with a suspension of the conidiospores of Helminthosporium teres and incubated in a moist chamber at 20 to 22 ° C. for 2 days. The plants were then cultivated in a greenhouse at 20 to 22 ° C. One week after the inoculation, the percentage attack on the leaf areas was noted. The fungicidal activity was calculated as follows:

The compounds were in the form of 20% formulations.

Compounds according to the invention Puccinia hordei% activity No. 500 ppm 100 ppm 20 ppm

10th

100

Infested in Treated -100

=% Effect

Infection in untreated The compounds were in the form of 20% formulations.

Compounds according to the invention Helminthosporium teres% Action No. 500 ppm 100 ppm 10 ppm

1

100

100

2nd

100

100

100

3rd

100

100

90

4th

95

95

90

5

100

100

6

99

7

8th

98 83

90

9

100

85

10th

95

95

11

100

90

12

94

90

13

92

85

14

89

80

15

94

90

16

94

80

17th

89

18th

100

70

19th

94

20th

70

23

85

24th

95

90

25th

95

95

26

80

27th

90

15

20th

25th

30th

35

Example 6

Effect of prophylactic leaf treatment against dwarf rust Puccinia hordei on barley in an air-conditioned plant growth chamber

Young barley plants in the stage of the first leaf were sprayed to runoff point with the specified concentration. After the spray coatings had dried on, the treated plants and untreated control plants were inoculated by painting over them with plants suffering from dwarf rust and brought into a plant growth chamber. The plants were cultivated for 10 days at 15 ° C. and in the first two days under almost moisture-saturated air. The percentage of leaf area affected by rust was then noted. The fungicidal activity was calculated as follows:

60

65

1

100

77

2nd

100

83

3rd

4th

100

100

89

5

100

100

94

6

100

94

7

100

98

89

8th

100

94

94

9

80

10th

100

98

94

11

89

12

84

13

89

14

95

80

15

95

16

78

17th

100

100

100

18th

98

19th

95

20th

85

21st

100

70

22

100

100

23

79

24th

90

70

25th

90

90

27th

85

30th

95

31

95

Example 7

Effect against Pseudomonas phaseolicola, causative agent of the bean fat stain disease, in vitro

Biomalt agar was cooled to about 45 ° C after heat sterilization and then - mixed with the test substances in an aqueous preparation - poured into plastic petri dishes. After the nutrient medium had solidified, the dishes treated with agar and dishes with untreated agar were inoculated as a control with a suspension of the fat stain pathogen Pseudomonas phaseolicola in the center by means of an inoculation loop. Then the dishes were incubated at 22 ° C. After 2 lA weeks the radial expansion of the colonies of the grown bacteria was measured. The bacteria-inhibiting effect was calculated as follows from the average of two repetitions per test element:

100-

55

Radial growth in treated -100 Radial growth in untreated

=% Inhibitory effect

The compounds were in the form of 20% formulations.

100-

Infestation in Treated-100 Infestation in Untreated

=% Effect

Connection according to the invention

% Effect with 250 ppm

No.

Drug concentration

12

62

15

73

21st

64

24th

66

653024

10th

Example 8

Steam activity against Helminthosporiumn teres on barley in the greenhouse

To determine the steam activity, a pot with approx. 20 barley seedlings at the stage of the beginning of the second leaf was placed between barley pots with a dried spray coating from a dripping wet treatment. The dripping wet treatment was carried out with an active ingredient concentration of 0.1%. A conidia suspension from the net stain pathogen Helminthosporium teres was sprayed over all three pots per test element, which was prepared with an aqueous solution of 0.05% sodium oleate and 0.02% gelatin and adjusted to 100,000 spores per milliliter. After the spores had been sprayed on, the three pots per test element were enclosed in polyethylene bags for three days and kept under greenhouse conditions of approximately 20.degree. The bags were then opened by cutting off the tips of the leaves. After 8 days, the number of net spots per pot was counted. The fungicidal steam effect was calculated from this as follows:

«Nn _ net spots on exposed barley-100 = 0 / w. ,

Mesh stains on unexposed barley ° ir Un®

The substances according to the invention were present as 20% formulations. All exposures to steam were compatible with plants.

Compound No.% effect according to the invention

2nd

3rd

4 10 13

100 100 99 100 85

Compound No. according to the invention

% Effect

12

100

13

100

14

100

Example 10

io Soy and wheat were pre-sprayed with emulsions of the test substances. The application rate was the equivalent of 2 kg of active ingredient / ha. The plants were then cultivated in the greenhouse and measured after three weeks.

15 The table shows the registered percentage growth inhibitions.

Compounds according to the invention Growth inhibition in ° /

20th

25th

"30

35

No.

soy

wheat

2nd

39

28

3rd

22

28

7

17th

7

9

0

17th

13

4th

14

14

17th

24th

18th

13

14

19th

4th

14

22

65

21st

23

30th

17th

25th

35

24th

26

35

24th

Comparative compound

2-chloroethyl trimethyl

ammonium chloride

0

17th

Comparative agent 1- (4-chlorophenoxy) -3,3-dimethyl-1 - (1,2,4-triazol-1-yl) -butanone

86

40 It can be seen that the compounds according to the invention are generally more potent than the comparison compound.

Example 9

Systemic effect of soil treatment before emergence against Erysiphe polygoni in the greenhouse

Plant pots were sprayed with 0.3 kg of active ingredient per hectare after sowing sugar beet and placed next to untreated pots in the greenhouse at about 20 ° C. After the beet plants had emerged (12 to 14 per pot), they waited until the plants had developed the first two leaves and then inoculated by dusting the dry spores of the beet powder Erysiphe polygoni. Three weeks later (six weeks after the soil treatment) the infestation of the leaves was rated. The fungicide effect could only be achieved by taking up the substances via the plant roots and was calculated as follows:

45

50

Example 11

Rice was treated with the compounds according to the invention at a rate of 2 kg of active ingredient / ha in advance. After three weeks of culture in the greenhouse, the percentage growth inhibition was determined.

This is shown in the table.

Compounds according to the invention Inhibition of growth in 9 no.

100-

Infestation in Treated-100 Infestation in Untreated

=% Effect

55

22

25th

26

60 Comparative compound 2-chloroethyl trimethyl ammonium chloride

11 7 14

The compounds were in the form of 20% formulations. 65

All treatments proved to be compatible with the growth inhibition of the compounds according to the invention.

Plants and resulted in a more vigorous, compact fertilization gives the comparative compound in the present

Grew in comparison with the untreated control. Application not.

11

653024

Example 12

Sugar beets were sprayed pre-emergence at a rate of 2 kg of active ingredient / ha. The percentage growth inhibition and the color of the plants were recorded after three weeks of greenhouse cultivation.

The results are shown in the following table.

Growth inhibition according to the invention in% coloring *

Connection no.

1

9

1

3rd

34

1

7

34

0

8th

37

0

9

25th

1

10th

37

0

12

22

0

13

41

0

14

41

0

16

53

0

17th

53

0

18th

22

1

19th

37

0

20th

37

1

21st

6

1

22

37

1

23

53

2nd

24th

22

1

25th

69

2nd

26

37

2nd

Means of comparison

2-chloroethyltri-

0

0

methyl ammonium

umchloride

* Table for coloring:

0 = like control

1 = more intense green

2 = dark green

The compounds according to the invention influence the beet growth, which is not achieved by the comparison compound in the present application.

% Effect according to the invention

Compound No. 500 ppm 100 ppm

100 100

91 80 90 100 100 95 95 95 90 80

99 90

100 99

100 97

100 98

98 93

90

97 90

97 90

100 98

25 Example 14

Effect of prophylactic leaf treatment against the leaf stain pathogen Cercospora beticola on sugar beets in the greenhouse.

Sugar beet plants with at least 2 well-developed 30 leaves were sprayed to runoff point with the stated concentrations. After the spray coatings had dried on, the treated plants and untreated control plants were sprayed with a conidia suspension of the Cercospora beticola and incubated in a greenhouse at 26 ° C. for 2 days in a moist manner. The plants were then cultivated under normal greenhouse conditions. The percentage of infestation was rated two weeks after the treatment.

The fungicidal activity was calculated as follows:

The compounds were in the form of 20% formulations.

% Effect with

500 ppm 100 ppm

40 100 infestation in treatment. 100 =% effect Infection in untreated

Compound No. according to the invention

2nd

5 3 9

12

13

14 io 16

17th

18th

19th

20th

is 22

23

24th

25th

26 20 27

29

30th

31

Example 13 50

Effect of prophylactic leaf treatment against the leaf stain pathogen Fusarium culmorum on millet (Pennisetum glaucum) in the greenhouse.

Young millet plants (approx. 30 per pot) at the stage of the beginning of the second leaf were sprayed to runoff with the given concentrations. After the spray coatings had dried on, the treated and the untreated control plants were sprayed with a conidia suspension of Fusarium culmorum and placed in a moist greenhouse at about 22 ° C. After 4 days, the percentage of leaf area affected was estimated. The fungicidal activity was calculated as follows:

Infection in Treated 100, 17. ,

100- ". TT —v-r— =% effect

Infestation m Untreated 65

The compounds according to the invention were in the form of 20% formulations.

3rd

100

100

11

93

12

93

13

100

14

93

16

100

17th

87

19th

93

20th

87

21st

100

96

22

100

100

23

100

100

24th

100

100

25th

96

96

26

100

96

27th

98

98

28

100

98

29

100

98

30th

100

100

31

100

100

653024

12

Example 15

Effect of seed treatment against seed-bearing Helminthosporium sativum (pathogen of foot disease) on barley.

Barley seed contaminated with Helminthosporium sativum was treated with 50 mg of active ingredient per 100 grams. From each treatment and from untreated, 2 g of seeds were sown in 2 repetitions in pots and incubated at 15 ° C. in a climatic chamber. From the emergence of the plants, artificial lighting was provided every 12 hours. After 4 weeks, the percentage of plants with foot diseases was determined. All plants were diseased in untreated.

a climate chamber set up. After the plants had emerged, lighting was artificially every 12 hours. Until the end of the experiment after 7 weeks, the diseased plants were counted weekly and removed. Overall, in the untreated control, 76.1% of the emerged plants fell ill. The protective effect of the treatment was calculated as follows:

100-

10th

Infestation in Treated -100 Infestation in Untreated

-% effect

The compounds according to the invention were in the form of 20% formulations.

Compound No. according to the invention

% Effect

2nd

100

3rd

99.5

4th

100

5

99.5

15

The compounds were in the form of 20% formulations. Example 16

Effect of seed treatment against seed-bearing phoma betae on sugar beet.

Sugar beet seed contaminated with Phoma betae was treated with 250 mg of active ingredient per 100 grams. From treated and untreated seeds, 4 repetitions of 25 seeds each were sown in pots and at 15 ° C in

Compound No. according to the invention

% Effect

2nd

100

3rd

97

20 4

97

5

100

6

83

12

92

13

99

25 14

96

Means of comparison

beta- (1,1'-biphenyl-4-yloxy) alpha

51

(1,1-dimethylethyl) -1 H-1,2,4-triazole-1 ■

30 ethanol

1 - (4-chlorophenoxy) -3,3-dimethyl-1 -

57

(1,2,4-triazol-1-yl) -2-butanone

B

Claims (61)

653 024 PATENT CLAIMS 1. 1,2,4-triazol-1-yl-propionitrile of the general formula O-Ri I. R-C-CHs- I. CN N = | 1 (I) in the R is an aromatic hydrocarbon radical optionally substituted one or more times, identically or differently, by halogen, (Ci-C4) alkyl, (Ci-C4) alkoxy, (Ci-C4) alkylthio, trifluoromethyl or the nitro group and Ri (Ci Cio) -alkyl, (C3-Cs) -alkenyl, (C3-C8) -alkynyl, or one optionally one or more times, identically or differently by halogen, (Ci-C4) -alkyl, (Ci-C4) -alkoxy , (Ci-C4) alkylthio, trifluoromethyl or the nitro group substituted phenylalkyl radical, and their acid addition salts with inorganic and organic acids. 2. 1,2,4-triazol-l-yl-propionitriIe according to claim 1, wherein R is optionally one or more, identical or different by halogen, (Ci-C4) alkyl, (Ci-C4) alkoxy, (Ci-C4) alkylthio, trifluoromethyl or the nitro group substituted phenyl radical and Ri (Ci-Cio) alkyl, (C3-Cs) alkenyl or an optionally one or more, identical or different by halogen, (Ci-C4) alkyl, (Ci-C4) alkoxy, (Ci-C4 ) -Alkylthio, trifluoromethyl or the nitro group substituted benzyl radical. 3. 2-isopropoxy-2-phenyl-3- (1,2,4-triazol-l-yl) propionitrile, hydronitrate according to claim 1. 4. 2-isopropoxy-2-phenyl-3- (l, 2,4-triazol-l -yl) propionitrile according to claim 1. 5. 2-hexyloxy-2- (2-methylphenyl) -3- (1,2,4-triazol-l-yl) propionitrile, hydronitrate according to claim 1. 6. 2-butoxy-2- (2-methylphenyl) -3- (1,2,4-triazol-l-yl) propionitrile according to claim 1. 7. 2-butoxy-2- (2-methylphenyl) -3- (l, 2,4-triazol-l-yl) propionitrile, hydronitrate according to claim 1. 8. 2-hexyloxy-2- (2-methylphenyl) -3- (l, 2,4-triazol ~ l-yl) propionitrile according to claim 1. 9. 2-butoxy-2-phenyl-3- (1,2,4-triazol-1-yl) propionitrile, hydronitrate according to claim 1. 10. 2-butoxy-2- (2-chlorophenyl) -3- (1,2,4-triazol-1-yl) propionitrile, hydronitrate according to claim 1. 11. 2-ethoxy-2-phenyl-3- (l, 2,4-triazol-l-yl) propionitrile, hydronitrate according to claim 1. 12. 2-phenyl-2-propoxy-3- (1,2,4-triazol-1-yl) propionitrile, hydronitrate according to claim 1. 13. 2- (3-chlorophenyl) -2-hexyloxy-3- (1,2,4-triazol-l-yl) propionitrile, hydronitrate according to claim 1. 14. 2-butoxy-2-phenyl-3- (1,2,4-triazol-l-yl) propionitrile according to claim 1. 15. 2-phenyl-2-propoxy-3- (1,2,4-triazol-l-yl) propionitrile according to claim 1. 16. 2-ethoxy-2-phenyl-3- (1,2,4-triazol-1-yl) propionitrile according to claim 1. 17. 2-Hexyloxy-2-phenyl-3- (l, 2,4-triazol-l-yl) propionitrile, hydronitrate according to claim 1. 18. 2-allyloxy-2-phenyl-3- (1,2,4-triazol-1-yl) propionitrile, hydronitrate according to claim 1. 19. 2-butoxy-2- (4-chlorophenyl) -3- (l, 2,4-triazol-l-yl) propionitrile, hydronitrate according to claim 1. 20. 2-allyloxy-2-phenyl-3- (1,2,4-triazol-1-yl) propionitrile according to claim 1. 21. 2-methoxy-2-phenyl-3- (1,2,4-triazol-l-yl) propionitrile according to claim 1. 22. 2-hexyloxy-2-phenyl-3- (1,2,4-triazol-l-yl) propionitrile according to claim 1. 23. 2- (2-chlorophenyl) -2-hexyloxy-3- (1,2,4-triazol-l-yl) propionitrile, hydronitrate according to claim 1. 5 24. 2- (2-chlorophenyl) -2-propoxy-3- (l, 2,4-triazol-l-yl) propionitrile, hydronitrate according to claim 1. 25. 2- (4-chlorophenyl) -2-propoxy-3- (l, 2,4-triazol-l-yl) propionitrile, hydronitrate according to claim 1. 26. 2- (4-chlorophenyl) -2-hexyloxy-3- (l, 2,4-triazoI-l-yl) -lo propionitrile, hydronitrate according to claim 1. 27. 2- (4-chlorophenyl) -2-propyloxy-3- (1,2,4-triazol-l -yl) propionitrile according to claim 1. 28. 2-butoxy-2- (4-chlorophenyl) -3- (1,2,4-triazol-l-yl) propionitrile according to claim 1. 15 29. 2- (2-methylphenyl) -2-octyloxy-3- (l, 2,4-triazol-l-yl) propionitrile, hydronitrate according to claim 1. 30. 2-decyloxy-2- (2-methylphenyl) -3- (1,2,4-triazol-l-yl) propionitrile, hydronitrate according to claim 1. 31. 2- (2-methylphenyl) -2-octyloxy-3- (l, 2,4-triazol-l-yl) -20 propionitrile according to claim 1. 32. 2- (2-chlorophenyl) -2-butoxy-3- (1,2,4-triazol-1-yl) propionitrile according to claim 1. 33. 2- (2-chlorophenyl) -2-propoxy-3- (l, 2,4-triazol-l-yl) propionitrile according to claim 1. 25 34. 2-Butoxy-2- (2,4-dichlorophenyl) -3- (l, 2,4-triazol-l-yl) propionitrile, hydronitrate according to claim 1. 35. 2-butoxy-2- (2,4-dichlorophenyl) -3- (1,2,4-triazol-l-yl) propionitrile according to claim 1. 36. 2-allyloxy-2- (2,4-dichlorophenyl) -3- (1,2,4-triazol-l-yl) -30 propionitrile according to claim 1. 37. 2- (3,4-dichlorophenyl) -2-propoxy-3- (l, 2,4-triazol-l-yl) propionitrile, hydronitrate according to claim 1. 3 8. 2- (3,4-dichlorophenyl) -2-propoxy-3- (1,2,4-triazol-1-yl) propionitrile according to claim 1. 35 39. 2- (3,4-dichlorophenyl) -2-hexyloxy-3- (l, 2,4-triazol-l-yl) propionitrile, hydronitrate according to claim 1. 40. 2- (3,4-dichlorophenyl) -2-hexyloxy-3- (1,2,4-triazol-l-yl) propionitrile according to claim 1. 41. 2- (4-fluorophenyl) -2-propoxy-3- (1,2,4-triazol-1-yl) -40 propionitrile, hydronitrate according to claim 1. 42. 2- (4-fluorophenyl) -2-propoxy-3- (1,2,4-triazol-l-yl) propionitrile according to claim 1. 43. 2-butoxy-2- (4-fluorophenyl) -3- (1,2,4-triazol-l-yl) propionitrile, hydronitrate according to claim 1. 45 44. 2-Butoxy-2- (4-fluorophenyl) -3- (1,2,4-triazol-l-yl) propionitrile according to claim 1. 45. 2- (2-fluorophenyl) -2-propoxy-3- (1,2,4-triazol-1-yl) propionitrile according to claim 1. 46. 2- (2-fluorophenyl) -2-propoxy-3- (1,2,4-triazol-1-yl) -50 propionitrile according to claim 1. 47. 2-butoxy-2- (2-fluorophenyl) -3- (1,2,4-triazol-l-yl) propionitrile, hydronitrate according to claim 1. 48. 2-butoxy-2- (2-fluorophenyl) -3- (1,2,4-triazol-1-yl) propionitrile according to claim 1. 55 49. 2- (2-fluorophenyl) -2-hexyloxy-3- (l, 2,4-triazol-l-yl) propionitrile, hydronitrate according to claim 1. 50. 2- (2-fluorophenyl) -2-hexyloxy-3- (1,2,4-triazol-1-yl) propionitrile according to claim 1. 51. 2- (4-bromophenyl) -2-propoxy-3- (1,2,4-triazol-l-yl) -60 propionitrile, hydronitrate according to claim 1. 52. 2- (4-bromophenyl) -2-propoxy-3- (1,2,4-triazol-l-yl) propionitrile according to claim 1. 53. 2- (4-bromophenyl) -2-hexyloxy-3- (l, 2,4-triazol-l-yl) propionitrile, hydronitrate according to claim 1. 65 54. 2- (4-bromophenyl) -2-hexyloxy-3- (1,2,4-triazol-l-yl) propionitrile according to claim 1. 55. 2- (2,4-dichlorophenyl) -2-propoxy-3- (l, 2,4-triazol-l-yI) propionitrile, hydronitrate according to claim 1. 56. 2- (2,4-dichlorophenyl) -2-propoxy-3- (1,2,4-triazol-1-yl) propionitrile according to claim 1. 57. 2- (2-methylphenyl) -2-pentoxy-3- (1,2,4-triazol-l-yl) propionitrile, hydronitrate according to claim 1. 58. 2- (2-methylphenyl) -2-pentoxy-3- (1,2,4-triazol-1-yl) propionitrile according to claim 1. 59. 2- (4-methylphenyl) -2-propoxy-3- (1,2,4-triazol-1-yl) propionitrile, hydronitrate according to claim 1. 60. 2-HexyIoxy-2- (4-methylphenyl) -3- (1,2,4-triazoI-l-yl) propionitrile, hydronitrate according to claim 1. 61. 2- (4-methylphenyl) -2-propoxy-3- (1,2,4-triazol-1-yl) propionitrile according to claim 1. 62. 2-Hexyloxy-2- (4-methylphenyl) -3- (1,2,4-triazol-1-yl) propionitrile according to claim 1. 63. 2-butoxy-2- (4-methylphenyl) -2- (1,2,4-triazol-1-yl) propionitrile according to claim 1. 64. Process for the preparation of 1,2,4-triazol-l-yl-propionitriles according to one of claims 1 to 63, characterized in that compounds of the general formula O-Ri I. R-C-CH2-Y (II) I. CN with 1,2,4-triazole of the formula N-CH II II HC N H or its alkali compounds in the presence of a solvent in which R 1 and R 2 have the meaning given above and Y is halogen or the alkylsulfonyloxy or arylsulfonyloxy radical optionally halogenated in the side chain. 65. Biocidal agent, characterized by a content of at least one compound according to one of claims 1 to 63. 66. Biocidal agents according to claim 65 with fungicidal activity. 67. Biocidal agents according to claim 65 with growth regulatory effect. 68. Biocidal agents according to claim 65 with bactericidal activity. 69. Biocidal agents according to claim 65 in a mixture with carriers and / or auxiliaries.