DD212641A5 - 1,2,4-TRIAZOL-1-YL-PROPIONITRILE-CONTAINING BIOZIDE MEDIUM - Google Patents

Abstract

The invention relates to 1,2,4-triazol-1-yl-propionitrile containing biocidal agent of general formula I in admixture with Traeger- and / or excipients. The agents according to the invention are biocidally effective in the broadest sense, but are distinguished in particular by a fungicidal action, in which they surprisingly exceed known active substances analogous constitution and direction of action. Other effects include growth-regulating and bactericidal effects. Because of the broad spectrum of activity recognized, the compounds are not only suitable for the protection of crop plants, but also for the protection of materials and the fight against human pathogenic and animal pathogenic microbes, resulting in a wide range of possible applications.

Description

Berlin, 17 · 2. 1984 - / - 62 194 18

Biocidal agent

Field of application of the invention

The invention relates to novel 1,2,4-triazol-i-yl-propionitrile containing biocidal agents, in particular with fungicidal action

• Characteristic of the known technical solutions

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

Object of the invention

The agents according to the invention are biocidally effective in the broadest sense, but are distinguished, in particular, by a fungicidal action in which, surprisingly, they exceed known active substances of analogous constitution and direction of action.

Explanation of the essence of the invention

O.

The object of the present invention is to develop novel propionitrile derivatives which open up wide-ranging application possibilities, in particular in the field of crop protection, and have a broad spectrum of fungicidal activity

  · ···· ''

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

62 194 18

R - C - CH ₀ 2

in the , *

R is an optionally mono- or polysubstituted by identical or different halogen, (Cj-C ^ alkyl, _(Cj-C4) alkoxy, (C ₁ -C ₄₎ -alkylthio, trifluoromethyl or Mtrogruppe substituted aromatic hydrocarbon radical and R ₁ (C ₁ -C ₁₀ ) -alkyl, (C ₃ -C ₈ ) -alkenyl, (C ₃ -C ₈ ) -alkynyl or an optionally mono- or polysubstituted by identical or different halogen, (C ₁ -C ₄ ) -alkyl, (CJ-C ₄₎ alkoxy, (Cj-C ₄₎ -alkylthio, trifluoromethyl or nitro substituted phenylalkyl

and their acid addition salts with inorganic and organic acids ·

The fungicidal action surprisingly extends to fungi of various systematic position. In the treatment of aboveground plant parts they protect against wind-borne pathogens · Against seed-borne pathogens you can use the compounds for seed treatment · They also act systemically, d. H. they are absorbed by the roots of the plants, for example, after sowing, are transported into the aerial parts of the plant and protect them against pathogens. ,

Further effects include growth-regulating and bactericidal action.

Because of the recognized broad spectrum of activity, the compounds are not only suitable for the protection of crops,

^ '62 194 18

but also for the protection of materials and for the control of human pathogenic and animal pathogenic microbes, resulting in a wide range of applications ·

Depending on the particular importance of the substituents, this results in areas of application in which the compounds exhibit outstanding effects. Thus, they can be used in each case as fungicides, plant growth regulators or bactericides.

In the compounds represented by the general formula I, 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, 2-propylphenyl, 3 -Propylphenyl, 4-propylphenyl, 2-isopropylphenyl, 3-isopropylphenyl, 4-isopropylphenyl, 2-butylphenyl, 3-butylphenyl, 4-butylphenyl, 2-sec-butylphenyl, Q 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-trifluoromethylphenyl, 4-trifluoromethylphenyl, 2-nitrophenyl, 3-ITitrophenyl, 4 -Mtrophenyl, 3-fluoro-4-methoxyphenyl, 3-chloro-5-nitrophenyl, 4-C hlor-2-fluorophenyl, 3ι4 »5-trimethoxyphenyl, or 2-chloro-2-nitrophenyl and

   "62 194 18 - 4 -

₁₁ Q for example methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, honyl, decyl, isopropyl, 2,2-dimethylpropyl-1,3,3-dimethyl-butyl-2, (C - Cg) Alkenyl, for example, 2-buten-1-yl, 3-methyl-2-buten-1-yl, hexenyl, heptenyl, octenyl, phenylalkyl, for example, benzyl, 2-pluorobenzyl, 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-methylbenzyl, 3-nitrobenzyl, 4-nitrobenzyl, 2-trifluoromethylbenzyl, 3-trifluoromethylbenzyl, 4-trifluoromethylbenzyl, 2-methoxybenzyl, 3-methoxybenzyl, 4-methoxybenzyl, 2-ethoxybenzyl, 3-ethoxybenzyl, 4-lthoxybenzyl , 2-propoxybenzyl, 3-propoxybenzyl, 4-propoxybenzyl, 2-butoxybenzyl, 3-butoxybenzyl, 4-butoxybenzyl, 2-methylthiobenzyl, 3-methylthiobenzyl, 4-methylthiobenzyl, 2-ethylthiobenzyl, 3-ethylthiobenzyl, 4-ethylthiobenzyl, 2 Butylthiobenzyl, 3-butylthiobenzyl, 4-butylthiob enzyl ·

As inorganic and organic acid for the formation of the acid addition salts are, for example, the Halogenwaseerstoffsäure, such as hydrochloric acid and hydrobromic acid, further phosphoric acid, sulfuric acid, especially nitric acid, mono- and bifunctional carboxylic acids and hydroxycarboxylic acids, such as acetic acid, maleic acid, succinic acid , Fumaric, tartaric, citric, salicylic, sorbic, lactic and sulfonic acids, such as p-toluenesulfonic acid and 1,5-naphthalenedisulfonic acid ·

These acid addition salts can be prepared by the usual salification methods, for example by dissolving a compound

62 194 18 - 5 -

the Pormel I can be obtained in a suitable Lösringsmittel and adding the acid ·

Of the compounds according to the invention are characterized by a fungicidal action, in particular those in which in the general Pormel I the rest

R is phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 3 ', 4-dichlorophenyl, 4-bromophenyl, 2-pluorophenyl, 4-pluorophenyl or 2-methylphenyl and

R _{1 is} ethyl, allyl, propyl, isopropyl, butyl or hexyl

Preferably, such compounds are to be mentioned, in which

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

Of outstanding activity are the following compounds according to the invention:

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

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

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

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

62 194 - 6 -

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

* 2-Butoxy-2- (4-chlorophenyl) -3- (1,2,4-triazol-1-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, - ^; Hydro nitrate

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

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

pionitrile,

2-Butoxy-2-phenyl-3- (1,2,4-triazol-1-yl) -propionitrile 2- (2-chlorophenyl) -2-butoxy-3- (1,2,4-triazole-1) yl) -propionitrile 2-lthoxy-2-phenyl-3- (1,2,4-triazol-1-yl) -propionitrile 2-allyloxy-2-phenyl-3- (1,2,4-triazole-1) yl) -propionitrile 2- (2-chlorophenyl) -2-propoxy-3- (1,2,4-triazol-1-yl) -propionitrile

The compounds according to the invention exhibit in particular fungicidal effects, but at the same time they are distinguished by growth-regulatory effects in a number of crop plants.

62 194 18 - 7 -

'Depending on the plant species and the application rate, herbicidal effects can also result «

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

- inhibition of vegetative growth in woody and herbaceous plants, for example on roadsides, railway tracks, etc. »to prevent lush growth · growth of crops in order to prevent storage or buckling, in cotton to increase breadth,

Influencing the branching of vegetative and generative organs in ornamental or crop plants for the propagation of the flower bud or in tobacco and tomato for the inhibition of side shoots,

- improvement of quality of the grapes, for example a sugar content increase in sugar cane, sugar beet or fruit, and a more even ripeness of the crop,

· Which leads to higher yields,

- Increasing the resistance to climatic influences such as cold and drought,

- influencing the latex flow in gum plants,

- Parthenocarp production, male sterility and gender influence are also possible applications,

Control of germination of seeds or budding of buds,

62 194 18 - 8 -

- Defoliation or influence of the fruit case for harvest relief

The compounds of the invention are particularly suitable for influencing the growth of beta-beets, but also show in cereals, soybean and cotton desired growth-regulating effects · ι

The application rates are depending on the application in general from 0.05 to 5 kg of active ingredient / ha, if necessary, higher application rates can be used.

The application time depends on the application target and the climatic conditions «

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

In addition to the aforementioned effects, the compounds according to the invention also have a bactericidal action which allows further possible uses *

The compounds of the invention may be used either alone, in admixture with each other or with other active ingredients. Optionally, other crop protection or pest control agents may be added depending on the desired purpose.

The labeled active substances or mixtures thereof are expediently used in the form of preparations, such as powders, scattering agents, granules, solutions, emulsions or suspensions,

- 62 194 18

with the addition of liquid and / or solid carriers or diluents and optionally wetting, adhesion, emulsifying and / or Mspergierhilfsmitteln applied.

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

Suitable solid carriers are mineral earths, for example, tonsil, silica gel, talc, kaolin, attapulgite, limestone, silicic acid and vegetable products, for example flours.

Surfactants include, for example, calcium lignosulfonate, polyoxyethylene alkylphenyl ethers, naphthalenesulfonic 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, it is also possible to admix dyestuffs in order to give the pickled seed 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 surfactants.

The application of the funds can be done in the usual way,

• ··

62 194 18 - 10 -

 -: i

For example, with water as a carrier in Spritzbrühmengen of about 100 to 1000 liters / ha »An application of funds in the so-called" low-volume ¹¹ or "ultra-low-volume method" is just as possible as their application in the form of so-called microgranules *

For the preparation of the preparations, for example, the following constituents are used:

Ac spray powder

a) 40 weight percent active ingredient

25 weight percent clay minerals 20 weight percent silica 10 weight percent cell pitch 5 weight percent surface active agents based on a mixture of the calcium salt of lignin sulfonic acid with alkylphenol polyglycol ethers

b) 25% by weight of active compound 60% by weight of kaolin

10 weight percent silica

5% by weight of surfactants based on the sodium salt of N-methyl-N-oleyltaurine and the calcium salt of lignosulfonic acid

e) 10% by weight of active ingredient 60% by weight of clay minerals 15% by weight of silica 10% by weight of cell pitch

5% by weight of surfactants based on the sodium salt of H-methyl-N-oleyltaurine and the calcium salt of lignosulfonic acid

62 194 - 11 -

B, paste

45% by weight of active ingredient 5% by weight of sodium aluminum silicate 15% by weight of cetyl polyglycol ether with 8 moles of ethylene oxide

2 weight percent spindle oil 10 weight percent polyethylene glycol 23 parts water

C> emulsion concentrate

25% by weight of active ingredient 15% by weight of cyclohexanone 55% by weight of xylene

5% by weight mixture of nonylphenylpolyoxyethylene or calcium dodecylbenzosulphonate ·

The novel compounds according to the invention can be prepared, for example, by reacting propionitriles of the general formula O-R ₁

RC-CH ₀ -Y II

2

^ CN

with 1,2,4-triazole of the formula

N - CH '

Il

HC N H

or its alkali metal compounds in the presence of a solvent and optionally in the presence of a base, wherein

 '.u' 62 194 18

- 12 -

R and R.J have the abovementioned meaning and Y is halogen or the optionally halogenated in the side chain alkylsulfonyloxy or arylsulfonyloxy radical.

As the halogen, for example, chlorine, bromine or iodine; Suitable alkylsulfonyloxy radicals are, for example, methyl, ethyl, propyl and the trifluoromethylsulfonyloxy group, and suitable arylsulfonyloxy radicals are, for example, the benzylsulfonyloxy and p-toluenesulfonyloxy groups.

The reaction can be carried out both with an excess of 1,2,4-triazole, if appropriate in the presence of a solvent, and with the addition of a strong base, for example sodium or potassium hydroxide. Triazole also use 1,2,4-triazole alkali metal. ,

Suitable solvents to the reactants inert substances are preferably polar, aprotic character such as N, IT-Dirth thylformamid, Ν, Ν-dimethylacetamide, N-methylpyrrolidone, tetramethylurea, hexamethylphosphoric triamide and benzonitrile, but also higher-boiling aromatic and aliphatic hydrocarbons such as toluene, chlorobenzene or xylene ·

The reaction temperature can be varied within wide limits. Preference is given to a temperature between 100 ⁰ C and 200 ⁰ C. The reactions are carried out under normal or elevated pressure.

The 1,2,4-triazol-1-yl-propionitriles according to the invention are generally almost colorless and odorless solids. The derived acid addition salts are also colored and

62 194 18

j: * - 13 -

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 dissolve partly in water and well in polar organic solvents such as acetonitrile, Ν, Ν-dimethylformaraid, lower alcohols, chloroform and methylene chloride

embodiments

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

example 1

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

Connection No. 2

To sodium hydride (0.55 mol) suspended in 50 ml of dry DMP are added 0.55 mol of 1,2,4-triazole with stirring and cooling. Thereafter, 0.11 mol of 2-isopropoxy-3-methylsulfonyloxy-2-phenyl-propionitrile are added in 50 ml of DMF and the mixture kept at 150 ⁰ C bath temperature for 1.5 hours. After cooling, it is extracted 3 times with 100 ml of ether, the combined ether phases are washed twice with water and dried with MgSO 4. The ether is rotated in vacuo, the residue is combined with 50 ml of isopropanol and 6.8 ml of nitric acid are added dropwise conc · a stirring · After addition of 80 ml of ether is stirred and then sucked "one crystallized from Isopröpanol to Fp · · still ^1/4 Hour: 185-189 ° C (decomposition) yield: 15 g = 43% of theory

DMP s dimethylformamide

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Example 2

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

Compound No. 3

10 g of 2-1sopropoxy-2-phenyl-3- (1 »2,4-triazol-1-yl) -propionitrile, hydronitrate are dissolved in methanol and treated with 8 ml of 32% ammonia water. It is added to water, extracted with ethyl acetate, dried over MgSO 4, the ethyl acetate is rotated under reduced pressure, treated with a little ethyl acetate and activated charcoal, boiled briefly, filtered off with suction and then turned back in. The resulting test substance is analytically pure.

PP *: 176 - 177 ⁰ C *.

Yield: 6.65 g = 83 % of theory

In analogous manner, the following compounds according to the invention can be prepared. ......

Physical No. Name of the compound Constant

1 2-Hexyloxy-2- (2-methylphenyl) -3- (1,2,4-Pp.:159-62 ⁰ C (Z) triazol-1-yl) -propionitrile, hydronitrate

^ ^ 4 2-Butoxy-2- (2-methylphenyl) -3- (1,2,4-pent .: 58-62 ⁰ C triazol-1-yl) -propionitrile

5 2-Butoxy-2- (2-methylphenyl) -3- (1,2,4-Pp.:158-61 ⁰ C (Z) triazol-1-yl) -propionitrile, hydronitrate

6 2-Hexyloxy-2- (2-methylphenyl) -3-η (1,2,4-triazol-1-yl) -propionitrile

7 2-Butoxy-2-phenyl-3- (1,2,4-triazole-1-Pp.:159-6O ⁰ C (Z) yl) -propionitrile, hydronitrate

8 2-Butoxy-2- (2-chlorophenyl) -3- (1,2,4-Pp.:142.5-44 ⁰ C)

triazol-1-yl) -propionitrile, hydronitrate

62 194 18

- 15 -

Physical No. Harne of Compound Constant

9 2-lthoxy-2-phenyl-3- (1,2,4-triazol-1 Pp.:169-70 ⁰ C (Z) yl) -propionitrile, hydronitrate

10 ^ -phenyl ^ -propoxy ^ -Ü ^^ - triazole-i-Pp .: 178-79 ⁰ C (Z) yl) -propionitrile, hydronitrate

11 2- (3-Chlorophenyl) -2-hexyloxy-3- (i, 2,4-Pp.:173-75 ⁰ C (Z) triazol-1-yl) -propionitrile, hydronitrate

12 2-Butoxy-2-phenyl-3- (1,2,4-triazole-1-PP: 67-68 ° C) .'-yl) -propionitrile

13 2-phenyl-2-propoxy-3- (1,2,4-triazole-Pp.:107-08 ⁰ C 1-yl) -propionitrile

14 2-ethoxy-2-phenyl-3- (1,2,4-triazol-1-Pp ,: 74-75 ⁰ O yl) -propionitrile

15 2-Hexyloxy-2-phenyl-3- (1,2,4-triazole-Pp.:158-60 ⁰ C (Z) 1-yl) -propionitrile, hydronitrate

16 2-Allyloxy-2-phenyl-3- (1,2,4-triazole-Pp.:145-47 ⁰ C (Z) 1-yl) -propionitrile, hydronitrate

17 2-Butoxy-2- (4-chlorophenyl) -3- (1,2,4-Pp.:173-75 ⁰ C (Z) triazol-1-yl) -propionitrile, hydronitrate

18 2-Allyloxy-2-phenyl-3- (1,2,4-triazole-Pp .: 86-88 ⁰ C 1-yl) -propionitrile

(J 19 2-Methoxy-2-phenyl-3- (1,2,4-triazole-1-pp .: 77-79 ⁰ C yl) -propionitrile

20 2-Hexyloxy-2-phenyl-3- (1,2,4-triazole-PP: 58-60 ⁰ C 1-yl) -propionitrile

21 2- (2-Chlorophenyl) -2-hexyloxy-3- (1,2,4-Pp.:157-59 ⁰ C (Z) 1-yl) -propionitrile, hydronitrate

22 2- (2-Chlorophenyl) -2-propoxy-3- (1,2,4-Pp.:138-39 ⁰ C (Z) triazol-1-yl) -propionitrile, hydronitrate

23 2- (4-Chlorophenyl) -2-propoxy-3- (1,2,4-Pp.:155-57 ⁰ C (Z) triazol-1-yl) -propionitrile, hydronitrate

Z β decomposition

62 194 18

Physical No. groves of compound * constant

24 2- (4-Chlorophenyl) -2-hexyloxy-3- (1,2,4-Fp.:155-59 ⁰ C (Z) triazol-1-yl) -propionitrile, hydronitrate

25 2- (4-chlorophenyl) -2-propyloxy-3- (1,2,4-Fp.:115-19°C triazol-1-yl) -propionitrile

26 2-Butoxy-2- (4-chlorophenyl) -3- (1,2,4-mp.:. 54-60 ⁰ C triazol-1-yl) -propionitrile

27 2- (2-methylphenyl) -2-octyloxy-3- (1,2,4-Pp.:128-34 ⁰ C (Z) triazol-1-yl) -propionitrile, hydronitrate

28 2-Decyloxy-2- (2-methylphenyl) -3- (1,2,4-Pp.:116-20 ⁰ C (Z) triazol-1-yl) -propionitrile, hydronitrate

29 2- (2-methylphenyl) -2-octyloxy-3-r (1,2,4- ⁿ D ²⁰ : 1,4930-triazol-1-yl) -propionitrile

30 2- (2-Clilorophenyl) -2-butoxy-3- (1,2,4- ³¹ D ⁴⁰ : 1,5273-triazol-1-yl) -propionitrile

31 2- (2-Chlorophenyl) -2-propoxy-3- (1,2,4- ³¹ D ⁴⁰ : 1,5308-triazol-1-yl) -propionitrile

32 2-Butoxy-2- (2,4-dichlorophenyl) -3- (1,2,4-Pp.:i63-66 ⁰ C triazol-1-yl) -propionitrile, hydronitrate

33 2-Butoxy-2- (2,4-dichlorophenyl) -3- (1,2,4-Pp .: 53-55 ⁰ C. triazol-1-yl) -propionitrile

34 2-Allyloxy-2- (2,4-dichlorophenyl) -3-Pp.:104-07 ⁰ C (1,2,4-triazol-1-yl) -propionitrile

35 2- (3,4-dichlorophenyl) -2-propoxy-3 x ^ Pp.:152-55 ⁰ G (Z) (1,2,4-triazol-1-yl) propionitrile,

Hydronitrate _?

36 2- (3,4-dichlorophenyl) -2-propoxy-B- Pp .: 60-66 ^0C (1,2,4-triazol-1-yl) -propionitrile

37 2- (3,4-dichlorophenyl) -2-hexyloxy-3- Pp.:166-68 ⁰ C (1,2,4-triazol-1-yl) -propionitrile, hydronitrate

Z β decomposition

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Physical No. Name of the compound long constant

38 2- (3,4-dichlorophenyl) -2-hexyloxy-3- ¹¹ D ^40: 1.5240 propionitrile (1,2,4-triazol-1-yl)

39 2- (4-Pluorphenyl) -2-propoxy-3- (1,2,4-Pp.:172-75 ⁰ O (Z) triazol-1-yl) -propionitrile, hydronitrate

40 2- (4-Pluorophenyl) -2-propoxy-3- (1,2,4-Pp.98- 100 ° C triazol-1-yl) -propionitrile

41 2-Butoxy-2- (4-fluorophenyl) -3- (1,2,4-Pp.:173-75 ° C (Z) triazol-1-yl) -propionitrile, hydronitrate

42 2-Butoxy-2- (4-fluorophenyl) -3- (1,2,4-Pp .: 56-58 ⁰ C. triazol-1-yl) -propionitrile

43 2- (2-Pluorophenyl) -2-propoxy-3- (1,2,4-Pp.:150-53°C (Z) triazol-1-yl) -propionitrile, hydronitrate

44 2- (2-Pluorophenyl) -2-propoxy-3- (1,2,4- _: m.p.:66-69 ° C triazol-1-yl) -propionitrile

45 2-Butoxy-2- (2-fluorophenyl) -3- (1,2,4-Pp.:138-43 ° C (Z) triazol-1-yl) -propionitrile, hydronitrate

46 2-Butoxy-2- (2-fluorophenyl) -3- (1,2,4-pent .: 76-79 ° C triazol-1-yl) -propionitrile

47 2- (2-Pluorophenyl) -2-hexyloxy-3- (1,2,4-Pp.:134-37°C (Z) triazol-1-yl) -propionitrile, hydronitrate

48 2- (2-Pluorophenyl) -2-hexyloxy-3- (1,2,4-pent .: 58-60 ° C triazol-1-yl) -propionitrile

49 2- (4-Bromophenyl) -2-propoxy-3- (1,2,4-Pp.:15O-53°C (Z) triazol-1-yl) -propionitrile, hydronitrate

50 2- (4-Bromophenyl) -2-propoxy-3- (1,2,4-Pp.:118-21 ⁰ C triazol-1-yl) -propionitrile

51 2- (4-Bromophenyl) -2-hexyloxy-3- (1,2,4-Pp.:161-64°C (Z) triazol-1-yl) -propionitrile, hydronitrate

52 2- (4-bromophenyl) -2-hexyloxy-3- (1,2,4-pent .: 6O-62 ° O triazol-1-yl) -propionitrile

Z β decomposition

62 194 18

j. physical

No. Name of the connection Constant

53 2- (2,4-dichlorophenyl) -2-prepoxy ^ - PP: 166-7O ° C (Z) 1,2,4-triazol-1-yl) -propionitrile,

Hydro nitrate

54 2- (2,4-dichlorophenyl) -2-propoxy) -3 -pp .: 61-63 ⁰ C (1,2,4-triazole) -propionitrile

55 2- (2-methylphenyl) -2-pentyl-3- (1,2,4-Pp.:151-54°C (Z) triazol-1-yl) -propionitrile, hydronitrate

56 2- (2-methylphenyl) -2-pentyl-3- (1,2,4- ⁿ D ⁴⁰ : 1,5111-triazol-1-yl) -propionitrile

57 2- (4-methyl-phenyl) -2-propoxy-3- (1,2,4-Pp..-170-71 ⁰ C (Z) triazol-1-yl) -propionitrile, hydronitrate

58 2-Hexyloxy-2- (4-methylphenyl) -3 -pp: 177-81 ° C (Z) (1,2,4-tria2ol-1-yl) -propionitrile, hydronitrate

59 2- (4-Methylphenyl) -2-propoxy-3- (1,2,4-Pp.:120-24 ⁰ C triazol-1-yl) -propionitrile.

60 2-hexyloxy-2- (4-niethyl-phenyl) -3- ^(1,2,4-21 D ^40: 1.5065 tria ^ ol-1-yl) -propionitrile

61 2-Butoxy-2- (4-methylphenyl) -3- (1,2,4-pp .: 71-73 ° C triazol-1-yl) -propionitrile

The 3-aryl- or 3-alkylsulfonyloxy-propionitriles of the general formula II with Y meaning aryl- or alkylsulfonyloxy to be used as starting materials have hitherto not been described in the literature.

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

^ · 62 194 18

- 19 -

Formula III

R-CH III

CN

wherein Round R ^ have the meaning given for formula I, hydroxymethylated according to methods known to eich and the thus obtained 3-hydroxypropionitriles of the general formula

0 - R ₁

R - 0 - CH ₀ - OH IV I ² CN

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

The following describes the preparation of a starting product.

, 3-methylsulfonyl "2-phenyl-2-propo3: y-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) are added to this suspension while cooling with ice 40 & Lge solution and stir vigorously. After a few hours (TLC check), the mixture is added to ice-water and extracted 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 drying.

62 194 18

- 20 -

Rotate in vacuo remains a colorless oil, which turns out to be uniform as thin-layer chromatography and can be further processed without further purification.

Yield: 28 ^ 4 g = 90 % of theory 3-hydroxy-2-phenyl-2-

propoxy-propionitrile

ⁿ D ²⁰ : 1.5027

28 g (0.136 mol) of 3-Hydro3cy-2-phenyl-2-propoxy-propionitrile are dissolved in 200 ml of toluene and treated with 19.5 g (0.171 mol) of methanesulfonyl chloride.

At 10 ⁰ C, 18.6 g (0.184 mol) of triethylamine are added dropwise. The mixture is stirred for 30 minutes at room temperature, 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 turns out to be pure by thin-layer chromatography.

Yield: 32.27 g = 86 % of theory 3-methylsulfonyl-2-phenyl-2-propoxy-propionitrile

n _D ²⁰ : 1.5000

The following working examples serve to illustrate the possible applications of the compounds according to the invention, which were carried out in the form of the above-mentioned preparations.

Example 3

Effect of prophylactic foliar treatment against powdery mildew Erysiphe graminis on barley in the greenhouse

Young barley plants in the stage of the first leaf were sprayed dripping wet with the specified concentrations. To

62 194 18

When the spray coverings dried on, the treated plants and untreated control plants were inoculated with dry powdery mildew porridges by coating the test plantlets with infested plants. Thereafter, the test plants were cultivated in the greenhouse at about 20 to 22 ° 0 and scored after one week for percent attack of the leaf area, the fungicidal action was calculated as follows:

Infested in Treated »100 ¹⁰⁰ - infestation in untreated = ^% ! ** **» «

The compounds were present as 20% formulations.

62 194 18

- 22 -

Invention Appropriate Connection No. * Erysiphe graminis % effect 500 ppm 100 ppm 95 1 " 100 59 2 100 100 3 100 100 4 100 95 5 , 100 94 6 100 100 7 100 100 8th 100 100 9 100 100 10 100 94 11 100 100 12 100 100 Ί3 100 100 14 100 100 .15 100 100 16 100 100 17 100 100 18 100 100 19 100 100 20 100 95 21 .100 100 22 100 100 23 100 24 100 - 25 100 26 ioo

62 194 18

Compound No. of the Invention · Erysiphe graminis

% Effect

500 ppm 100 ppm

28 30 31 33 34 35 36 38 41 42 44 48

49 50 51 52 53

54 55

57 58 59 60 61

100 95 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 95 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100 100

, 62 194 18 - 24 Example 4

Effect of prophylactic leaf treatment against Erysiphe cichoracearum on pumpkin plants in the greenhouse

With the indicated concentrations of active compound until dripping wet sprayed squash plants vrurden after the spray coating by dusting dry mildew spores of Erysiphe ciohoracearum inoculated with inoculated untreated control plants in the greenhouse at 24 ⁰ C incubated · ilsch a week the affected mildew surface was estimated as a% of the total leaf area. The fungicidal activity was calculated as follows:

100 - 100 'infestation treated _{= % ν ± ν1αχα &} infestation in untreated

The note "s" in the table below indicates that the fungicidal effect was also assessed by the growth of the plants (after the treatment) and was found to be positive. That is to say, the active substances were systemically transported into the growth and were also effective against it Mildew·

The compounds according to the invention were present as 20% formulations »

62 194 18

Inventive compounds ETr. Erysiphe cichoracearum % Effect 250 25 5 2.5 10Os 100s 100s 0.5 ppm 1 10Os 10Os 100s 100s 2 10Os 10Os 100s 100s 3 100s 100 100s 98 100 5 100s 100s 100 6 100s 100s 100 7 100 100s 100 8th 100s 100s 100 9 10Os 100s 10 10Os 100s 100 11 10Os 100 100 12 10Os 100 100 13 10Os 100s 14 10Os 100s 100 15 10Os 100 100 , 16 10Os 99.5 17 10Os 100 100s 18 10Os 100 100 , 19 10Os 97 20 10Os 21 , 10Os 90 22 £ 100 100

; _u ί '· ", 62 194

- ^2S -

>'.'Erysiphe cichoracearum % Effect Compound No. 250 ppm

100s 100s 100s 100s 100s 100s 100s 100s 100s 100s 100s

27 29 32 37 39 40 S S 43 , 45 46 47 • 56

 '.u "62 194 18

- 27 Example 5

Effect {%) of prophylactic foliar treatment against Helminthosporium teres (= Pyrenophora teres), net blotch of barley

Young barley plants at the stage of first leaf were sprayed ( '% with the indicated concentrations until dripping wet. After drying of the spray deposits the treated plants and untreated control plants were sprayed with a suspension of conidiospores of Helminthosporium teres and in a humid chamber for 2 days at 20 to 22 ⁰ C. Thereafter, the plants were cultured in the greenhouse at 20 to 22 ^° C. One week after the inoculation, the percentage attack of the leaf surfaces was recorded. The fungicidal activity was calculated as follows:.

100 - infestation treated * 100 _{= % Effect} Infestation in untreated

The compounds were present as 20-term formulations.

62 194 18

- 28 -

Helminthosporium teres

invention % Effect 98 100 ppm 10 ppm  - * Connections Kr · 500 ppm 83 100 1 - 100 100 100 100 2 100 95 100 90 3 100 100 95 90 4 95 94 100 "5 ' 100 92 99 6 - 89 90 7 94 I 8th 94 85 9 89 95 10 100 90 11 94 90 12 70 85 13 • 85 80 14 95 90 , 15 95 80 16 80 17 90 70 18 19 20 23 90 24 95 25 26 27

62 194 18 - 29 Example 6

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

Young barley plants at the stage of first leaf were sprayed to drip point with a specified concentration · After drying of the spray deposits the treated plants and untreated control plants were inoculated with a sweep of dwarf rust infected plants and placed in a plant growth chamber · At 15 ⁰ C and in the two first layers under almost moist saturated The plants were cultivated for 10 days in air. The percentage of rust-infected leaf area was then recorded. The fungicidal activity was calculated as follows:

100 - Infestation Treated 100 _{= % Effect} Infestation in Untreated

The compounds were present as 20-term formulations.

62 194 18

- 30 -.

According to the invention, compounds Nos. Puccinia % effect 500 ppm hordei 100 ppm 20 ppm 1 100 77 2 100 83 3 4 100 100 ⁸ 9 5 100 100 94 6 100 94 7 100 98 89 8th 100 94 94 9 80 10 100 98 94 11 89 12 84. 13 89 14 95 80 15 95 16 78 17 100 100 100 18 98 19 95 20 85 21 100 70 22 100 100 23 79 24 90 · 70 25 90 90 27 85 30 • 95 31 95

^ "62 194 18

Example 7

Action against Pseudomonas phaseolicola, the pathogen of bean pettiness, in vitro

Biomalzagar was cooled after heat sterilization to about 45 ⁰ C and then - mixed with the test substances in aqueous preparation - poured into Kunststoffpetrischalen · Each of the solidification of the medium were the shells treated agar (3 and trays with untreated agar as a control with a suspension of Pettfleckenerregers Pseudomonas . phaseolicola inoculated in the center using an inoculating loop Then the trays were incubated at 22 ⁰ C incubated · After 2 ^1/2 weeks, the radial extent of the grown colonies of bacteria was measured from the average of two repetitions of each test member the bacteria inhibiting effect was calculated as follows.:

Radial growth treated in · 100 ¹⁰⁰ - Radial growth in untreated = * Heating effect

The compounds were present as 20% formulations.

% Action according to the invention with 250 ppm compounds no

12 62

15 73

21 64

24 66

62 194 18 - 32 -

Example 8

Vapor activity against Helminthosporium teres on barley in the greenhouse

To determine the vapor activity, a pot of approximately barley seedlings at the stage of the beginning second leaf was placed between two barley pots with dried sprayed coating of a drip-wet treatment. The dripping wet treatment was associated with a drug concentration of 0.1% run J Service. Over all three pots per test member, a conidia suspension was sprayed from the mesh spot exciter Helminthosporium teres, which had been prepared with an aqueous solution of 0.05 % sodium oleate and 0.02% gelatin and adjusted to 100,000 spores per milliliter. After spraying, the spores of the three pots were each test link in polyethylene bag included for three days and kept under greenhouse conditions of about 20 ⁰ C. The bags were then opened by cutting at the level of the leaf tips. After 8 days, the number of net spots per pot was counted. From this, the fungicidal vapor effect was calculated as follows:

J 100 - Net stains on exposed barley · 100

^{Web spots on unexposed} barley ⁼ ^ ^Wlrkun S

The substances according to the invention were present as 20% formulations. All steam expositions were plant-tolerable.

62 194 18

- 33 - ·. Compounds of the invention

No. % Effect 2 100 3 100 4 99 10 100 13 85 Vergleicbsmittel 1- (4-chlorophenoxy) -3,3-dimetyl- 1- (1,2,4-triazol-1-yl) -butanone 86

62 194 18 - 34 Example 9

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

Pots were to Zuckerrübeneinsaat sprayed with 0.3 kg of active substance per hectare and placed beside untreated pots in a greenhouse at etwa- 20 ⁰ C · Uach emergence of the sugar beet plants (12 to 14 per pot) were waiting until the plants developed the first two true leaves Erysiphe polygoni was then inoculated by sputtering on the dry spores of the beetroot powder mill. · Three weeks later (six weeks after soil treatment) the infestation of the leaves was scored · The fungicidal effect could only be achieved by absorption of the substances via the plant roots and became as follows calculated:

100 - infestation treated. 100 _{= % effect}

Infestation in untreated.

The compounds were present as 20% formulations. All treatments were found to be compatible with the plants and resulted in a sturdier, stouter growth compared to the untreated control.

invention

Compounds No. % Effect

12 100

13 100

14. '100

62 194 18 - 35 -

Example 10

Soya and wheat were sprayed in advance with emulsions of the test substances · The application rate was equivalent to 2 kg of active ingredient / ha · Then the plants were cultivated in a greenhouse and measured after three weeks »

The table shows the registered percentage growth inhibitions.

Growth Inhibition According to the Invention in % Compounds No. Soya Wheat

3 "

Compared connection

2-Chloräthyltrimethyl-

ammonium chloride 0 17

It is found that the compounds according to the invention are generally more effective than the comparison compound.

39 28 22 28 17 7 0 17 4 14 17 24 13 14 4 14 65 21 30 17 35 24 35 24

62 194 18 - 36 Example 11

Rice was treated with the compounds according to the invention in an amount of 2 kg of active ingredient / ha in the first run · After three weeks of culture in a greenhouse, the percentage growth inhibition was determined.

This is listed in the table ·

Growth inhibition according to the invention

Connections Nr * in %

22 11,

25 '7

26 '· · 14

Comparative compound 2-Ohloräthyltrimethylammoniumchlorid O

The growth inhibition of the compounds according to the invention does not give the comparative compound in the present application.

, 62 194 18

- 37 -

Example 12

Sugar beets were sprayed in pre-emergence at a rate of 2 kg of active ingredient / ha · The percentage inhibition of growth and the color of the plants was registered after three weeks greenhouse culture · The results show the following table.

Invention compounds Mr · Growth inhibition in % Coloring* 1 9 1 3 34 1 7 34 ο 8th 37 0 9 ' 25 1 10 37 0 12 22 0 13 41 0 14 41 0 16 53 0 17 53 0 18 22 1 19 37 0 20 37 1 21 6 1 22 37 1 23 53 2 24 22 1 25 69 2 26 37 2 Verbleichsmittel 2-chloroethyltrimethylammonium chloride 0 0

62 194 18 - 38 -

⁺ Table for staining: O «like control

1 β intense green

2 «= dark green

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

· *>'*. · Example 13

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

Young millet plants (about 30 per pot) at the beginning of the second leaf were sprayed dripping wet with the indicated concentrations * After the spray coatings had dried, the treated and untreated control plants were sprayed with a conidia suspension of Fusarium culmorum and humid at about 22 ^° C. in the greenhouse After 4 days, the percentage of affected leaf area was estimated. The fungicidal activity was calculated as follows:

100 - 100 'infestation treated _{= % effective} infestation in untreated

The compounds of the invention were present as 20% formulations.

2 3

9 12 13 14 16 17 18 19 20 22 23 24 25 26 27 29 30 31

62 194 18 - 39 -

% Effect according to the invention with compounds 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

62 194 18 - 40 -

Example 14

Effect of prophylactic foliar treatment against the leaf speckle pathogen Cercospora beticola on sugar beets in the greenhouse S

Sugar overgrowths with at least 2 well-formed leaves were sprayed to drip point with the indicated concentrations. After drying of the spray deposits the treated plants and untreated control plants with a conidia suspension of Cercospora were sprayed beticola and 2 days humid at 26 ⁰ C in the greenhouse incubated · Thereafter, the plants were grown under normal greenhouse conditions "Two weeks after the treatment was the percentage infestation. scoring.

The fungicidal activity was calculated as follows:

100 - 100 'infestation treated _{= % viral} infestation in untreated

The compounds were present as 20% formulations.

62 194 18

invention % Effect with 100 ppm Connections Dir · 500 ppm 100 3 100 11 93 12 93 ¹ 3 100 14 93 16; 100 17 87 19 93 20 87 96 21 100 100 22 100 100 23 100 100 24 100 96 25 96 96 26 100 98 27 98 98 28 100 98 29 100 100 30 100 100 31 100

62 194 18 - 42 Example 15 ''

Effect of seed treatment on seed-borne Helminthosporium sativum (causative agent of foot disease) on barley

Barley seeds contaminated with Helminthoporium sativum were treated with 50 mg of active ingredient per 100 grams. From each treatment as well as from untreated, 2 g seed were sown in pots in 2 repetitions and incubated at 15 ° C in a climatic chamber. The emergence of the plants was artificially illuminated every 12 hours. After 4 weeks the percentage of foot-sick plants was determined. In untreated, all plants were affected.

invention % Effect Connections no. 2 100 3 99.5 4 100 5 99.5

'Me compounds were available as 20% formulations.

62 194 18 - 43 Example 16

Effect of seed treatment against seedy Phoma betae on sugar beet

With Phoma betae contaminated sugar beet seeds were treated with 250 mg of active ingredient required per 100 gram · of treated and untreated seed 4 repetitions were seeded to 25 per grain in pots and chamber set at 15 ⁰ C in an air-W · After emergence of the plants was in the Artificially illuminated 12-hour rhythm · The diseased plants were counted and removed weekly until the end of the test after 7 weeks. · In the untreated control, 76.1 % of the accumulated plants fell ill · The protective effect of the treatment was calculated as follows:

100 - Infestation Treated 100 _{= % Effect} Infestation in Untreated

The compounds according to the invention were present as 20-term formulations.

62 194

invention

Compounds No · % effect

2. 100

"3 97

4 97

5 100

6 '83 12 92

) 13 99

14 96 comparison means

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

dimethylethyl) -1H-1,2,4-triazole-1-ethanol 51

1- (4-chlorophenoxy) -3,3-dimethyl-1- (1,2,4-

triazol-1-yl) -2-butanone 57

Claims (64)

1 # biocidal agent, characterized by a content of at least one 1,2,4-triazol-i-yl-propionitrile of the general formula RC-OH ₂ -If ^ I in the R is an optionally mono- or polysubstituted identically or differently by halogen, (C ₁ -C ₄ ) -alkyl, (C ₁ -C 4) -alkoxy, (C ₁ -C 4) -alkylthio, trifluoromethyl or the kitro group-substituted aromatic Hydrocarbon radical and R _{1 is} (C ₁ -C ₁₀ ) -alkyl, (C ₃ -C ₈ ) -alkenyl, (C ₃ -C ₈ ) -alkynyl, or an optionally mono- or polysubstituted by identical or different halogen, (C ₁ -) C.) - Alkyl, (C ₁ -C.) - Alkoxy, (C ₁ -C.) - Alkylthio, trifluoromethyl or the M-tro group substituted phenylalkyl radical and their acid addition salts with inorganic and organic acids, in admixture with carriers and / or auxiliaries, 2 · Means according to item 1, characterized in that R is an optionally mono- or polysubstituted, identically or differently, by halogen, (C ₁ -C ₄ ) -alkyl, (C ₁ -C 4) -alkoxy, (C ₁ -C 4) -alkylthio, trifluoromethyl or the hitrogroup substituted phenyl radical and R ₁ (Cj-C ₁ Q) -AlkVl, (C ₃ -C ₈ ) alkenyl or optionally one or more times, the same or different 3 * Agent according to item 1, characterized in that it contains as active ingredient isopropoxy-2-phenyl-3- (1,2,4-triazol-1-yl) -propionitrile, hydronitrate. 4. Composition according to item 1, characterized in that it contains as active principle 2-isopropoxy-2-phenyl-3- (1,2,4-triazol-1-yl) -propionitrile. 5. Composition according to item 1, characterized in that they contain as active ingredient 2-hexyloxy-2- (2-methylphenyl) -3- (1,2,4-triazol-1-yl) -propionitrile, hydronitrate · 6 · Composition according to item 1, characterized in that it contains as active ingredient 2-butoxy-2- (2-methylphenyl) -3- (1,2,4-triazol-1-yl) -propionitrile · 7 »Means according to item 1, characterized in that they contain as active ingredient 2-butoxy-2- (2-methylphenyl) -3- (1,2,4-triazol-1-yl) -propionitrile, hydronitrate · 8 # Agent according to item 1, characterized in that it contains as active ingredient 2-hexyloxy-2- (2-methylphenyl) -3- (1,2,4-triazol-1-yl) -propionitrile. 9 * Agent according to item 1, characterized in that it contains as active ingredient 2-butoxy-2-phenyl-3- (1,2,4-triazol-1-yl) propionitrile, hydronitrate. 10 · Means according to item 1, characterized in that they 11 »Composition according to item 1, characterized in that they contain as active ingredient 2-ethoxy-2-phenyl-3- (1,2,4-triazol-1-yl) -propionitrile, hydronitrate · 12. Composition according to item 1, characterized in that it contains as active ingredient 2-phenyl-2-propoxy-3- (1,2,4-triazol-1-yl) -propionitrile, hydronitrate. 13. Composition according to item 1, characterized in that it contains as active ingredient 2- (3-chlorophenyl) -2-he3-yloxy-3- (1,2,4-triazol-1-yl) -propionitrile, hydronitrate. 14. Composition according to item 1, characterized in that it contains as active ingredient 2-butoxy-2-phenyl-3- (1,2,4-triazol-1-yl) -propionitrile. 15 * Means according to item 1, characterized in that they contain as active ingredient 2-phenyl-2-propoxy-3- (1,2,4-triazol-1-yl) -propionitrile · 16. Composition according to item 1, characterized in that it contains as active ingredient 2-ethoxy-2-phenyl-3- (1,2,4-triazol-1-yl) -propionitrile. 17. Composition according to item 1, characterized in that it contains as active ingredient 2-hexyloxy-2-phenyl-3- (1,2,4-triazol-1-yl) propionitrile, hydronitrate. 18. Composition according to item 1, characterized in that it contains as active ingredient 2-allyloxy-2-phenyl-3- (1,2,4-triazol-1-yl) -propionitrile, hydronitrate. 19. Composition according to item 1, characterized in that it contains as active ingredient 2-butoxy-2- (4-chlorophenyl) -3- (1,2,4-triazol-1-yl) -propionitrile, hydronitrate. 20. Composition according to item 1, characterized in that it contains as active ingredient 2-allyloxy-2-phenyl-3- (1,2,4-triazol-1-yl) -propionitrile. 21 »Composition according to item 1, characterized in that they contain as active ingredient 2rMethoxy-2-phenyl-3- (1,2,4-triazol-1-yl) -propionitrile · 22 · Agent according to item 1, characterized in that it contains as active ingredient 2-hexyloxy-2-phenyl-3- (1,2,4-triazol-1-yl) -propionitrile · 23 * Means according to item 1, characterized in that they serve as Active ingredient 2- (2-chlorophenyl) -2-hexyloxy-3- (1,2,4-triazol-1-yl) -propionitrile, hydronitrate. 24. Composition according to item 1, characterized in that it contains as active ingredient 2- (2-chlorophenyl) -2-propoxy-3- (1,2,4-triazol-1-yl) -propionitrile, hydronitrate. Composition according to item 1, characterized in that it contains as active ingredient 2- (4-chlorophenyl) -2-propoxy-3- (1,2,4-triazol-1-yl) -propionitrile, hydronitrate. 26 # Means according to item 1, characterized in that they contain as active ingredient 2- (4-chlorophenyl) -2-hexyloxy-3- (1,2,4-triazol-1-yl) -propionitrile, hydronitrate. 27. Composition according to item 1, characterized in that it contains as active ingredient 2- (4-chlorophenyl) -2-propyloxy-3- (1,2,4-triazol-1-yl) -propionitrile. 28, Composition according to item 1, characterized in that they contain as active ingredient 2-butoxy-2- (4-chlorophenyl) -3- (1,2,4-triazol-1-yl) -propionitrile. 29 * Composition according to item 1, characterized in that they contain as active ingredient 2- (2-methylphenyl) -2-octyloxy-3- (1,2,4-triazol-1-yl) -propionitrile, hydronitrate. 30 * Means according to item 1, characterized in that they contain as active ingredient 2-decyloxy-2- (2-methylphenyl) -3- (1,2,4-triazol-1-yl) -propionitrile, hydronitrate. 31 "means according to item 1, characterized in that they contain as active ingredient 2- (2-methylphenyl) -2-octyloxy-3- (1,2,4-triazol-1-yl) -propionitrile. 32. Means according to item 1, characterized in that they contain as active ingredient 2- (2-chlorophenyl) -2-butoxy-3- (1,2,4-triazol-1-yl) -propionitrile. 33. Composition according to item 1, characterized in that it contains as active ingredient 2- (2-chlorophenyl) -2-propoxy-3- (1,2,4-triazol-1-yl) -propionitrile. 34. Composition according to item 1, characterized in that it contains as active ingredient 2-butoxy-2- (2,4-dichlorophenyl) -3- (1,2,4-triazol-1-yl) -propionitrile, hydronitrate. 35. Composition according to item 1, characterized in that it contains as active ingredient 2-butoxy-2- (2,4-dichlorophenyl) -3- (1,2,4-triazol-1-yl) -propionitrile. 36. Composition according to item 1, characterized in that they contain as active ingredient 2-allyloxy-2- (2,4-dichlorophenyl) -3- (1,2,4-triazol-1-yl) -propionitrile. 37. Composition according to item 1, characterized in that it contains as active ingredient 2- (3 »4-dichlorophenyl) -2-propoxy-3- (1,2,4-triazol-1-yl) -propionitrile, hydronitrate * 38. Composition according to item 1, characterized in that they contain as active ingredient 2- (3,4-dichlorophenyl) -2-propoxy-3- (1,2,4-triazol-1-yl) -propionitrile. 39. Composition according to item 1, characterized in that it contains as active ingredient 2- (3,4-dichlorophenyl) -2-hexyloxy-3- (1,2,4-triazol-1-yl) -propionitrile, hydronitrate. 40. Composition according to item 1, characterized in that it contains as active ingredient 2- (3,4-dichlorophenyl) -2-hexyloxy-3- (1,2,4-triazol-T-yl) -propionitrile * 41. Composition according to item 1, characterized in that they contain as active ingredient 2- (4-pluorophenyl) -2-PrOpOXy ^ - (1,2,4-triazol-1-yl) -propionitrile, Hydronitat. Λ. 42. Composition according to item 1, characterized in that it contains as active ingredient 2- (4-pluorophenyl) -2-propoxy-3- (1,2,4-triazol-1-yl) -propionitrile. 43 # Means according to item 1, characterized in that they serve as Active ingredient 2-butoxy-2- (4-fluorophenyl) -3- (1,2,4-triazol-1-yl) -propionitrile, containing hydronitrate 44. Composition according to item 1, characterized in that they contain as O active ingredient 2-butoxy-2- (4-fluorophenyl) -3- (1,2,4-triazol-1-yl) -propionitrile. 45. Composition according to item 1, characterized in that it contains as active ingredient 27 (2-fluorophenyl) -2-propoxy-3- (1,2,4-triazol-1-yl) -propionitrile, . ' -45 - Invention san epruch 46. Composition according to item 1, characterized in that it contains as active ingredient 2- (2-fluorophenyl) -2-propoxy-3- (1,2,4-triazol-1-yl) -propionitrile. 47. Composition according to item 1, characterized in that it contains as active ingredient 2-butoxy-2- (2-fluorophenyl) -3- (1,2,4-triazol-1-yl) -propionitrile, hydronitrate. 48. Composition according to item 1, characterized in that it contains as active ingredient 2-butoxy-2- (2-fluorophenyl) -3- (1,2,4-triazol-1-yl) -propionitrile. - 48 - 49. Composition according to item 1, characterized in that it contains as active ingredient 2- (2-pluorophenyl) -2-hexyloxy-3- (1,2,4-triazol-1-yl) -propionitrile, hydronitrate. 50. Composition according to item 1, characterized in that it contains as active ingredient 2- (2-pluorophenyl) -2-liexyloxy-3 '- (1,2,4-triazol-1-yl) -propionitrile » 51 ♦ Composition according to item 1, characterized in that they contain as active ingredient 2- (4-bromophenyl) -2-propoxy-3- (1,2,4-triazol-1-yl) -propionitrile, hydronitrate. - 51 - 52 »Composition according to item 1, characterized in that it contains as active ingredient 2- (4-bromophenyl) -2-propoxy-3- (1,2,4-triazol-1-yl) -propionitrile · ^ 53 - ^{62 194 18} 53. Composition according to item 1, characterized in that it contains as active ingredient 2- (4-bromophenyl) -2-hexyloxy-3- (1,2,4-triazol-1-yl) -propionitrile, hydronitrate. 54. Means according to item 1, characterized in that they contain as active ingredient 2- (4-bromophenyl) -2-hexyloxy-3- (1,2,4-triazol-1-yl) -propionitrile. 55. Means according to item 1, characterized in that they contain as active ingredient 2- (2,4-dichlorophenyl) -2-propoxy-3- (1,2,4-triazol-1-yl) -propionitrile, hydronitrate. 56. Composition according to item 1, characterized in that it contains as active ingredient 2- (2,4-m-chlorophenyl) -2-propoxy-3- (1,2,4-triazol-1-yl) -propionitrile. 57. Composition according to item 1, characterized in that it contains as active ingredient 2- (2-methylphenyl) -2-pentyl-3- (1,2,4-triazol-1-yl) -propionitrile, hydronitrate. 58. Composition according to item 1, characterized in that they contain as active ingredient 2- (2-methylphenyl) -2-pentyl-3- (1,2,4-triazol-1-yl) propionitrile. : 59. Composition according to item 1, characterized in that it as active ingredient 2- (4-methylphenyl) -2-propoxy-3- (1,2,4-triazol-1-yl) -propionitrile, Hydroni-stepped contain. Q '' 60. Composition according to item 1, characterized in that they contain as active ingredient 2-hexyloxy-2- (4-ethyl-phenyl) -3- (i, 2,4-triazol-1-yl) -propionitrile, hydronitrate. 61, Composition according to item 1, characterized in that they contain as active ingredient 2- (4-methyl-phenyl> * 2-propoxy-3- (1,2,4-triazol-1-yl) - * propionitrile. 62, Composition according to item 1, characterized in that they contain as active ingredient 2-hexyloxy-2- (4-methyl-phenyl) -3-O, 2,4-triazol-1-yl) -propionitrile. 62 194 18 - 52 - ^ "'. ·' 62 194 18 62 194 18 - 50 - 62 194 18 - 49 - • 62 194 18 • 62 194 18
- 47 - as active ingredient 2-butoxy-2- (2-chlorophenyl) -3- (1,2,4-triazol-1-yl) -propionitrile, hydronitrate. 62 194 18 Halogen, (C ₁ -O ₄ ) alkyl, (C ₁ -C ₄ ) alkoxy, - (C, -C ₄ ) alkylthio, trifluoromethyl or the nitro group substituted benzyl radical. 62 194 18     ' 63. Composition according to item 1, characterized in that they contain as active ingredient off 2-butoxy-2- (4-methyl-phenyl) -3- (1,2,4-triazol-1-yl) -propionitrile. 64. Biocidal agent, characterized by a content of at least one compound according to items 1 to 63 in admixture with carriers and / or excipients.