HU189649B - Fungicide, bactericide and plant growth regulating compositions containing 1,2,4-triazol-1-yl-propionitrile derivatives as active substances and process for preparing the active substances - 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 for the control of human pathogenic and animal pathogenic microbes, resulting in a wide range of possible applications.

Description

FIELD OF THE INVENTION The present invention relates to a fungicidal, bactericidal and plant growth regulating composition containing 1,2,4-triazol-1-yl-propionitrile derivatives and a process for their preparation.

German Patent Publication No. 26 04 047 already discloses fungicidal imidazolyl propionitrile derivatives. However, formulations containing these as active ingredients are not applicable in practice because of their narrow spectrum of action.

It is therefore an object of the present invention to provide and use novel propionitrile derivatives which are useful as formulations in a broad field of plant protection and have a broad spectrum of fungicidal activity.

For this purpose, the compositions of the present invention have been prepared which contain an active ingredient of a 1,2,4-triazol-1-yl-propionitrile of formula (I)

R is phenyl optionally mono- or di-substituted with C 1 -C 4 alkyl at most, and

R 1 is C 1 -C 10 alkyl or C 3 -C 6 alkenyl, and acid addition salts thereof, preferably with nitric acid.

The formulations containing the compounds of formula (I) are predominantly fungicidal, which, surprisingly, outperforms the formulations of similar structure and activity.

This effect surprisingly extends to fungi from a wide variety of taxonomic units. When treated with the above-ground parts of the leaves, the preparations provide protection against pathogens transmitted by the wind. The compositions of the invention protect against seed-borne pathogens by seed dressing. In addition, the formulations act systemically, i.e. they are taken up by treatment of the roots of the plant, for example at sowing, and transported to the above-ground parts of the plant, thus providing protection against pathogens.

Other effects of the compositions of the invention include plant growth regulating and bactericidal effects.

Due to the aforementioned broad spectrum of activity, the compositions of the present invention can be used not only for crop protection but also for material protection, thus increasing the potential for use.

Depending on the particular meaning of each substituent, there may be certain particularly useful applications where the compounds exhibit quite excellent activity. The compositions may be fungicidal, plant growth regulating or bactericidal.

For example, each substituent in the compounds of formula (I) may be as follows: R is phenyl, 2-fluorophenyl, 3-fluorophenyl,

4-fluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 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-ethyl phenyl, 4-ethylphenyl, 2-propylphenyl, 3-propylphenyl, 4-propylphenyl, 2-isopropylphenyl, 3-isopropylphenyl, 4-isopropyl- phenyl, 2-butylphenyl, 3-butylphenyl, 4-butylphenyl, 2-sec-butylphenyl, 4-sec-butylphenyl, 2-tert-butylphenyl, , 3-tert-butylphenyl, 4-tert-butylphenyl.

R 1 is C 1 -C 10 alkyl, for example, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, isopropyl, 2,2-dimethyl. propyl-1,3,3-dimethyl-butyl-2-group, C 3 -C 6 -alkenyl such as 2-buten-1-yl, 3-methyl-2-buten-1-yl, hexenyl.

The acid addition salts are preferably formed with nitric acid.

The acid addition salts may be prepared by dissolving a compound of formula (I) in a suitable solvent, such as by dissolving a compound of formula (I) and then adding an acid.

Preferred fungicidal compositions are those which contain the active ingredient of formula (I)

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

Rj is ethyl, allyl, propyl, isopropyl, butyl or hexyl.

Particularly preferred are formulations containing the active compounds of formula (I)

R is phenyl, 4-chlorophenyl, or 2-methylphenyl, and

Rj is propyl, isopropyl, or butyl.

In particular, if the following ^T óanyagokat containing compositions are useful:

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-dronitrate,

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

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

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

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

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

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

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

2- (hexyloxy) -2- (2-methylphenyl) -3- (1,2,4-triazol-1-yl) -p: opionitrile hydronitrate,

2-oxy-2-phenyl-3- (1,2,4-triazol-1-yl) -propionitrile-h: dronitrate,

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) prop-21-pyronitrile hydroxyphenyl,

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

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

2-oxo-2-phenyl-3- (1,2,4-triazol-1-yl) -propionyl,

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

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

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

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

The compositions of the present invention are predominantly fungicidal, but also exhibit plant growth regulating activity in many crop plants.

They also have a herbicidal action, depending on the type of plant and the amount used.

Because the compositions of the present invention cause both qualitative and quantitative changes in plants and at the same time changes in metabolism, they can also be used as plant growth regulators and may be used in the following applications:

Inhibition of vegetative growth in woody and herbaceous plants such as roadside bushes, railway equipment, etc. excessive growth can be avoided. Inhibition of growth in cereals to prevent overturning or fracture and increase of yield of cotton.

Controlling the vegetative and reproductive branching of ornamental and crop plants, increasing the number of flowers or, in the case of tobacco and tomatoes, inhibiting side shoots.

Improving the quality of the fruit, for example in the case of sugar cane, sugar beet or fruits, ensures a more even ripening of the fruit, which leads to higher yields.

Increase resistance to weather conditions such as cold and drought.

Influence of latex yield on rubber plantations.

Creation of seedless fruits in the form of sterile dust and influence on sex.

Control of germination of seeds or budding of buds.

FoliageProach, or to control the harvest of crops, to control the fall of the crop.

Thus, the compositions of the present invention are particularly useful for controlling the growth of sugar beet, but also exhibit plant growth regulating activity in cereals, soy and cotton.

Depending on the field of application, the application rates of the formulations will generally be from 0.05 to 5 kg of active ingredient / ha, although higher doses may be employed.

The time of application depends on the purpose of the application and the weather conditions.

Surprisingly, the compositions of the present invention have a broader spectrum of activity and a greater potency than those known hitherto in the art.

As mentioned above, the compositions of the present invention have, in addition to the above effects, a bactericidal effect which allows their further use.

The compositions of the invention may be used alone or in admixture with other active ingredients. The compositions of the present invention may be in the form of a mixture of the active ingredient and at least one excipient, in powder, dust, granulate, solution, emulsion or suspension and liquid and / or solid carriers, and optionally containing wetting, tackifying, emulsifying and / or dispersing aids.

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

Solid carriers include minerals such as Tonsil, silica gel, talc, kaolin, attapulgite, limestone, silica, and plant products such as flour.

Examples of surfactants are lithium lignin sulfonate, polyoxyethylene alkylphenyl ether, naphthalenesulfonic acids and their salts, formaldehyde condensates, fatty alcohol sulfates and substituted benzenesulfonic acids and their salts.

When the active ingredients are used for seed dressing, the formulations are colored with i; can be blended to give the treated seeds a clearly recognizable color.

The proportion of active ingredient within the above formulations may vary within wide limits. For example, the compositions may contain from 10% to 90% by weight of active ingredient, from 90% to 10% by weight of a solid or liquid carrier, and optionally up to 20% by weight of surfactant.

Application of the composition can be effected by methods known per se, for example using water as a carrier, using a spray of about 100-1000 L / ha. In the case of so-called "Low-Volume" or "Ultra-Low-Volume", the compositions of the invention may also be administered in the form of microgranules.

For example, the following ingredients may be used to formulate compositions:

A) Spraying agent

a) 40% by weight of 2-isopropoxy-2-phenyl-3- (1,2,4-thiazol-1-yl) -propionitrile. HN0 ₃ % w / w clay mineral wt% silicic acid w / w silica gel wt% surfactant: lignin sulphonic acid calcium salt / alkylphenyl poly (glycol ether) mixture

b) 25% by weight of 2-isopropoxy-2-phenyl-3- (1,2,4-thiazol-1-yl) -propionitrile. HN0 ₃ 60% w / w kaolin 10% w / w silica, surfactant: mixture of N-methyl-N-oleyl taurine sodium and calcium salt of lignin sulfonic acid

c) 10% by weight of 2-isopropoxy-2-phenyl-3- (1,2,4-thiazol-1-yl) -pTOpionitrile. HNO3 60% by weight clay minerals 15% by weight silica with 10% by weight celium resin by weight surfactant: sodium salt of N-methyl-N-oleyl taurine and lignosulfonic acid3

189,649 Mixture of cinnamic salt.

d) 90% by weight of 2-isopropoxy-2-phenyl-3- (1,2,4-triazol-1-yl) -propionitrile] hydronitrate? surfactant: mixture of calcium ligning sulphonate and sodium salt of N-methyl-N-oleyl laurine

e) 20 weight? 2-Isopropoxy-2-phenyl 3- (1,2,4-triazol-1-yl) -propionitrile hydronitrate 60 wt. kaolin 15% by weight of silica? surfactant: a mixture of calcium lignin sulfonate and sodium salt of N-methyl-N-oleyl taurine.

B) Paste weight? Mass of 2-isopropoxy-2-phenyl-3- (1,2,4-triazol-yl) -propionitrile? sodium aluminosilicate 15 wt.% cetyl poly (glycol ether) (8 moles ethylene oxide) wt. reel oil 10 weight? poly (ethylene glycol) weight? water

C) Emulsion Concentrate Weight ?; Mass of 2-isopropoxy-2-phenyl-3- (1,2,4-triazol-yl) -propionitrile? cyclohexanone 55 weight? xylene (b) nonylphenyl polyoxyethylene or calcium dodecylbenzene sulfonate.

Compounds of formula (I) may be prepared by reacting a propionitrile of formula (II) with 1,2,4-triazole I or an alkali metal compound thereof in the presence of a solvent and optionally a base wherein R and R 1 are as defined above and Y is alkylsulfonyloxy.

The reaction may be carried out in excess of 1,2,4-triazole, optionally in the presence of a solvent, or by addition of a strong base such as sodium or potassium hydroxide. Alternatively, an alkali metal compound of 1,2,4-triazole may be used instead of 1,2,4-triazole.

Suitable solvents for the reactants are inert materials, preferably polar aprotic solvents such as N, N-dimethylformamide, Ν, Ν-dimethylacetamide, N-methylpyrrolidone, tetramethylurea, hexamethylphosphoric triamide and benzonitrile. however, higher boiling point aromatic and aliphatic hydrocarbons such as toluene, chlorobenzene or xylene can also be used.

The reaction temperature may vary within wide limits. Preferably, the reaction temperature is between 100 and 200 ° C. The reaction can be performed at normal pressure or at high pressure.

The 1,2,4-triazol-1-yl-propionitrile derivatives obtained by the process of the present invention are generally almost colorless and odorless solids. The acid addition salts thereof are also colorless and odorless crystalline compounds. The free bases are very slightly soluble in water, while they are more or less soluble in organic solvents, such as alcohols, ethers or chlorinated hydrocarbons. The acid addition salts are partially soluble in water but are also highly soluble in polar solvents such as acetonitrile, Ν, Ν-dimethylformamide, lower alcohols, chloroform and methylene chloride. The following examples further illustrate the preparation of the active compounds of the present invention.

Example 1

2-1 Zopropoxy-2-phenyl-3- (1,2,4-triazol-1-yl) propionitrile hydronitrate (Compound # 2)

To a stirred suspension of sodium hydride (0.55 mol, 50 ml in dry dimethylformamide) was added 0.45 mol of 1,2,4-triazole. A solution of 2-isopropoxy-2- (methylsulphonyloxy) -2-phenylpropionitrile (0.11 mol) in dimethylformamide (50 ml) was added and the mixture was heated at 150 ° C for 1.5 hours. After cooling, the mixture was extracted with ether (3 x 100 mL), and the combined ether layers were washed twice with water and dried over anhydrous magnesium sulfate. The ether is then evaporated in vacuo, 50 ml of 7-propanol are added to the residue and 6.8 ml of concentrated nitric acid is added dropwise under cooling with stirring. After adding 80 ml of ether, the mixture was stirred for an additional quarter hour and then filtered off with suction. The crystalline material is recrystallized from isopropanol.

__ Mp .: 185-189 * 0 (during decomposition). Yield:

43t 15g = ^25%.

Example 2

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

3q 10 g of 2-isopropoxy-2-phenyl-3- (1,2,4-triazol-1-yl) -propionitrile. HNO ₃ was dissolved in methanol and 8 mL of 32% aqueous ammonium hydroxide solution was added. The mixture was then diluted with water, extracted with ethyl acetate, dried over anhydrous magnesium sulfate, the ethyl acetate was evaporated in vacuo, a little ethyl acetate and charcoal were added, and the mixture was briefly boiled, suctioned and evaporated again. . The solid thus obtained is analytically pure. 176-177 ° C. Yield: 6.65 g = 83%.

By the methods of Examples 1 and 2, the following compounds were prepared:

Take over number and name Physical constant

7th

8th

9th

159-62 ° C (dec.)

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

2-Butaxy-2- (2-methylphenyl) -3-m.p. 58-62 ° C

- (1,2,4-triazol-1-yl) -propionyl.

nitrile

158-61 ° C (dec.)

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

2- (hexyloxy) -2- (2-methylphenyl) nf? = 1.5121

33? , 2,4-triazol-l-yl) -propionitrile

2-butoxy-2-phenyl-3- (l, 2,4-triazol1- yl) propionitrile hydro nitrate, m.p .: 159-60 ^° C

2-butoxy-2- (2-chlorophenyl) -3-, m.p.

-hidronitrát

2-Ethoxy-2-phenyl-3- (1,2 ₎ 4-triazole m.p. 169-70 ° C 1-yl) -propionitrile hydronitrate (decomposition)

189,649

10. 1-Phenyl-2-propoxy-3- (1,2,4-triazol-1-yl) -propionitrile hydronitrate

11. 2- (Chloro-phenyl) -2- (hexyloxy) -3- (1,2,4-triazol-1-yl) -propionitrile hydronitrate

12. 2-Butoxy-2-phenyl-3- (1,2,4-triazol-1-yl) -propionitrile

13. 2-Phenyl-2-propoxy-3- (1,2,4-triazol-1-yl) -propionitrile

14. 2-Ethoxy-2-phenyl-3- (1,2,4-triazol-1-yl) -propionitrile

15. 2- (Hexyloxy) -2-phenyl-3- (1,2,4-triazol-1-yl) propionitrile hydronitrate

16. 2- (Allyloxy) -2-phenyl-3- (1,2,4-triazol-1-yl) -propionitrile hydronitrate

17. 2-Butoxy-2- (4-chlorophenyl) -3- (1,2,4-triazol-1-yl) propionitrile hydronitrate

18. 2- (Allyloxy) -2-phenyl-3- (1,2,4-triazol-1-yl) propionitrile

19. 2-Methoxy-2-phenyl-3- (1,2,4-triazol-1-yl) -propionitrile

20. 2- (Hexyloxy) -2-phenyl-3- (1,2,4-triazol-1-yl) propionitrile

21. 2- (2-Chloro-phenyl) -2- (hexyloxy) -3- (1,2,4-triazol-1-yl) -propionitrile hydronitrate

22. 2- (2-Chlorophenyl) -2-propoxy-3Op: 178-79 ° C

4C.

4 '.

42nd

43rd

44th

45th

173-75'C (dec)

Mp: 67-68 ° C Mp: 107-08 ° C Mp: 74-75∞C

Mp: 158-60°C (decomposition)

145-47 ° C (dec.)

173-75 ° C (dec.)

86-88 ° C Melting point: 77-79 ° C Melting point: 58-60 ° C

Mp: 157 - 59 ° C (decomposition)

138-39 ° C. (1,2,4-Triazol-1-yl) -propionitrile (decomposition) hydronitrate

23. 2- (4-Chloro-phenyl) -2-propoxy-3-op.:155-57∞C - (1,2,4-triazol-1-yl) -propionitrile (decomposition) hydronitrate

24. 2- (4-Chloro-phenyl) -2- (hexyloxy) -3-m.p. 155-59 ° C - (1,2,4-triazol-1-yl) -propionitrile (decomposition) hydronitrate

25. 2- (4-Chloro-phenyl) -2- (propyloxy) - m.p. 115-195 ° C -3- (1,2,4-triazol-1-yl) propionitrile

26. 2-Butoxy-2- (4-chlorophenyl) -3-m.p. 54-60 ° C - (1,2,4-triazol-1-yl) propionitrile

27. 2- (2-methylphenyl) -2- (octyloxy) - m.p. 128-34 ° C -3- (1,2,4-triazol-1-yl) -propio (decomposition) nitrile hydro nitrate

28. 2- (Decyloxy) -2- (2-methylphenyl) -3-melting point: 116-20 ° C -3- (1,2,4-triazol-1-yl) propionite- ( decomposition) ril hydronitrate

29. 2- (2-methylphenyl) -2- (octyloxy) ^-3-O n0 = 1.4930 (1,2,4-triazol-1-yl) -propionitrile

30. 2- (2-Chlorophenyl) -2-butoxy-3- (1,2,4 * --------------------- Example 1 , 5273 np * 1.5308

163-66 ° C.

-tnasal-1 -u j -propiomtru

31. 2- (2-Chloro-phenyl) -2-propoxy-3- (1,2,4-triazol-1-yl) -propionitrile

32. 2-Butoxy-2- (2,4-dichlorophenyl) -3- (1,2,4-triazol-1-yl) propionitrile hydronitrate

33. 2-Butoxyl-2- (2,4-dichlorophenyl) -347.

48th

49th

50th

51st

52nd

53rd

54th

Op.:53-55°C

- (1,2,4-Triaz61-1-yl) -propionitrile 34. 2-Allyloxy) -2- (2,4-dichlorophenyl) -Op: 104-07 ° C

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

2- (3,4-dichloro-phenyl) -2-propoxy ,: mp 152-55 C ^E -3- (l, 2,4-triazol-l-yl) propionyl (dec) nitrile hydro nitrate

2- (3,4-dichlorophenyl) -2-propoxyl-m.p. 60-66 ° C

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

2- (3,4-Dichlorophenyl) -2- (hexyloxy) -3 <1,2,4-triazol-1-yl) propio-Mp 166-68 ° C Nitrile Hydronitrate <3 , 4-dichloro-r-phenyl) -2 - (hexylene) = 1.5240

oxy) -3- (1,2,4-triazol-1-yl) propionitrile

2- (4-fluorophenyl) -2-propoxy-m.p. 172-75 ° C -3- (1,2,4-triazol-1-yl) -propio- (decomposition) nitrile hydronitrate

2- (4-fluorophenyl) -2-propoxy-3-m.p. 98-100 ° C <1,2,4-triazol-1-yl) propionitrile 2-butoxy-2- (4-fluoro- phenyl) -3-Mp: 173-75 ° C - (1,2,4-triazol-1-yl) -propionitrile (decomposition) hydronitrate

2-Butoxy-2- (4-fluorophenyl) -3-melting point: 56-58 ° C

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

2- (2-Fluoro-phenyl) -2-propoxy-3- {1,2,4-triazol-1-yl) -propiomtril-hydronitrate 2- (2-fluoro-phenyl) -2-propoxy-3- ( 1,2,4-triazol-1-yl) -propionitrile

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

Mp: 150-53'C (dec)

M.p. 66-69 ° C

138-43 ° C (dec.)

2-butoxy-2- (2-fluorophenyl) -3 · m.p. 76-79 ° C

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

2- (2-Fluorophenyl) -2- (hexyloxy) -3-m.p. 134-37 ° C - (1,2,4-triazol-1-yl) propio (decomposition) nitrile hydro nitrate

2- (2-Fluorophenyl) -2- (hexyloxy) - m.p. 58-60 ° C

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

2- (4-Bromo-phenyl) -2-propoxy-m.p. 150-53 ° C

- (1,2,4-Triazol-1-yl) -propio (decomposition) nitrile hydronitrate

2- (4-Bromo-phenyl) -2-propoxy-3-m.p. 118-21 ° C - (1,2,4-Triazol-1-yl) -propionitrile 2- (4-Bromo-phenyl) - 2- (hexyloxy) - m.p .: 161-64 C ^e -3- (l, 2,4-triazol-1-yl) propionyl (dec) nitrilo nitrate hydrochloride

2- (4-Bromo-phenyl) -2- (hexyloxy) - m.p. 60-62 ° C

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

2- (2,4-dichlorophenyl) -2-propoxy-m.p. 166-70 ° C

-3,4,2,4-Triazol-1-yl) -propio (decomposition) nitrile hydronitrate

212-2,4-dichlorophenyl) -2-propoxy-3- (1,2,4-triazol-1-yl) -proplo-m.p. 61-63 ° C nitrile

55. 2- (2-Methylphenyl) -2- (pentyloxy-3- (1,2,4-triazol-1-yl) propionyl] m.p. 151-54 ° C

56. 2- (2-Methylphenyl) -2- (pentyloxy) nf? = 1.5111 -3- (1,2,4-triazol-1-yl) -propionitrile

57. 2- (4-Methylphenyl) -2-propoxyl-3- m.p. 170-71 ° C

- (), 2,4-Triazol-1-yl) -propio (decomposition). nitrile hydro nitrate

58. 2- (Hexyloxy) -2- (4-methylphenyl) -341,2,4-triazol-1-yl) -proplo-m.p. 177-81 ° C nitrile hydronitrate (decomposition)

59. 2- (4-Methylphenyl) -2-propoxy-3 Mp .: 120-44 ° C - (1,2,4-Triazol-1-yl) propionitrile

60. 2- (Hexyloxy) -2- (4-methylphenyl)) -O ° = 1.5065 -3- (1,2,4-triazol-1-yl) propionitrile

61. 2-Butoxy-2- (4-methyl-phenyl) -3-m.p.71-73 ° C - (1,2,4-triazol-1-yl) -propionitrile

The 3-alkylsulfonyloxypropionitrile derivatives of the general formula (II) where Y is an alkylsulfonyloxy group are new compounds. They are prepared by methods which are partially known or known per se (e.g., Rubin et al., Jacs 67, 192 f (1945), Hess et al., Bér. Dt. Chem. Ges. 50, 394 (1917)). phenylacetonitriles of the formula wherein R and Rj are hydroxymethylated according to methods known per se and the resulting 3-hydroxypropionitriles of formula IV are obtained with appropriate sulfonic acid derivatives such as sulfonic acid chlorides, optionally with the addition of an acid binder. The hydroxymethyl compounds of formula IV are also novel.

The preparation of a starting material is described below.

3- (Methylsulfonyloxy-2-phenyl-2-propoxy-propionitrile g (0.154 mol) 2-phenyl-2-propoxy-acetonitrile was dissolved in 120 ml of pyridine and 18.5 g (0.614 mol) of para-formaldehyde were added. While cooling with ice, tetrabutylammonium hydroxide (TBAOH) (7.7 ml) was added as a 40% solution, and the mixture was stirred vigorously. The ethereal phase was washed with dilute hydrochloric acid, brine and dried over magnesium sulfate. Yield: 28.4 g = 90% 3-hydroxy-2-phenyl-2-propoxypropionitrile.

n'A = 1.5027.

3-Hydroxy-2-phenyl-2-propoxypropionitrile (g, 0.136 mol) was dissolved in toluene (200 mL) and methanesulfonic acid chloride (19.5 g, 0.171 mol) was added. At 10 ° C, 18.6 g (0.184 mol) of triethylamine are added dropwise. After stirring for another 30 minutes at room temperature, the precipitated triethylamine hydrochloride was filtered off and the mixture was evaporated. The residue was taken up in ether, washed with water, dried over magnesium sulfate and evaporated. The oily residue is pure by thin layer chromatography. Yield: 32.27 g = 86% of 3- (methylsulfonyloxy-2-phenyl-2-propoxy-propionitrile).

n ⁷ J = 1.5000.

The following examples illustrate various uses of the compositions of the invention.

Example 3

Effect of preventive leaf treatment against true powdery mildew (Erysiphe graminis) in barley, greenhouse

Young barley plants in leaf condition were sprayed with dripping moisture at the concentration indicated. After the spray juice had dried, the treated plants as well as untreated control plants were inoculated with dry powdery mildew spores by rubbing the experimental plants with infected plants. The experimental plants were then grown in a greenhouse at 20-22 ° C, and after one week, the percentage of leaf surfaces was determined. The fungicidal effect was calculated using the following equation:

i nn Infection of the treated plant. 100 _

Infection is the untreated control effect

The active compounds were used as a 20% spray powder. The results are shown in the table below:

Serial number of compound in the preparation Erysiphe graminis% 500 ppm © © First 100 95 Second 100 59 Third 100 100 4th 100 100 5th 100 95 6th 100 94 7th 100 100 8th 100 100 9th 100 100 10th 100 100 11th 100 94 12th 100 100 13th 100 100 14th 100 100 15th 100 100 16th 100 100 17th 100 100 18th 100 100 19th 100 100 20th 100 100 21st 100 100 22nd 100 100 23rd 100 100 24th 100 25th 100 26th 100 28th 100 95 30th 100 100 31st 100 100 33rd 100 100 34th 100 100 35th 100 100 36th 100 100 38th 100 100 41st , 100 100 42nd 100 100 44th 100 100 48th 100 95 49th 100 100

189,649

salt. 100 100 51st 100 100 52nd 100 100 53rd 100 100 54th 100 100 55th 100 100 57th 100 100 58th 100 100 59th 100 100 60th 100 100 61st 100 100

Example 4

Effect of Preventive Leaf Treatment on Erysiphe cichoracearum on Pumpkin Plants in a Greenhouse The pumpkin plants sprayed to dripping moisture at the specified concentration were inoculated with a 24% control and inoculated with dry powdery mildew spores, after inoculation with Erysiphe cichoracearum. After a week, the powdery mildew surfaces were expressed as a proportion of the total leaf area. The fungicidal effect was calculated using the following equation:

] 0 - 100 infections in treated plants, <y. _O3 Infection in untreated plants

Note "s" in the following table means that the fungicidal effect also influenced the growth of the plants and was positively evaluated. This means that the active ingredients were systematically delivered to the overgrown parts of the plant after treatment and thus exhibited 100% activity against powdery mildew. The active compounds were used in the experiment as 20% spray powder.

The compound has 5 serial numbers of Ersiphe cichoracearum% active ingredient

27th Loos 29th Loos 32 ' Loos 37 Loos 39 Loos 40 Loos 43 Loos 45 Loos 46 Loos 47 Loos 56 Loos

Example 5

Effect of Preventive Leaf Treatment (%) on Helminthosporium teres (= Pyrenophora teres), Wet Spotting of Barley

Single-leaf young barley plants are sprayed to the dripping moisture at the indicated concentration. After the spray juice had dried, treated plants and untreated control plants were spray-sprayed with a suspension of Helninthosporium teres conldio spores and incubated for two days in a humidity chamber at 20-22 ° C. The plants were then grown in a greenhouse at 20-22 ° C. One week after infection, the percentage of leaf surfaces was found to be infected. The fungicidal effect was calculated from the following equation:

100

Infection of treated plant. 100

Infection of untreated plant =% effect

The active compounds were alkylated as 20% spray powder.

Helminthosporium teres% active compound in preparation% Ersiphe cichoracearum% pA 500 ppm 100 ppm 10 ppm

prodrugs 250 25 5 2.5 0.5 First 100 100 number ppm 40 Second She 100 100 100 juu 100 90 First Loos Loos Loos 4th 95 95 90 Second Loos Loos Loos 5th 100 100 Third Loos Loos Loos 6th 99 4th Loos Loos 100 7th 98 90 5th Loos Loos 100 45 8th 83 6th Loos Loos 100 9th 100 85 7th 100 100 100 10th 95 95 8th Loos 98 100 11th 100 90 9th Loos Loos Loos 12th 94th 90 10th Loos Loos 100 13th 92 85 11th Loos Loos 100 50 14th 89 80 12th Loos Loos 100 15th 94 90 13th Loos 16th 94 90 14th Loos Loos 100 17th 89 15th Loos 100 100 18th 100 70 16th Loos 100 99.5 55 19th 94 17th Loos Loos Loos 20th 70 18th Loos Loos 100 23rd 85 19th Loos 100 97 24th 95 90 20th Loos 25th 95 95 21st Loos 100 90 26th 80 22nd Loos 100 100 60 27th 90

Example 6

Effect of Preventive Leaf Treatment on Puceinia Horde Small Rust in Barley, Air Conditioned

Single-leaf young barley plants were sprayed to dripping moisture at the indicated concentrations. After spray drying, the treated plants as well as the untreated control plants were inoculated by rubbing with rust-infected plants and placed in a growth chamber. At 15 ° C and near saturated air humidity for the first two days, the plants were grown for 10 days. The percentage of rust-infected leaf surfaces was then determined. The fungicidal activity was calculated from the following formula:

100- Honeysuckle, θ _=% . _effect .

Untreated plant ferto / jae

The active compounds were used as a 20% spray powder.

Serial number of compound in the preparation Puceinia hordei% effect 500 ppm 100 ppm 20 ppm First 100 77 Second 100 83. Third 4th 100 100 89 5th 100 100 94 6th 100 94 7th 100 98 89 8th 100 94 94 9th 80 10, 100 98 94 11th 89 12th 84 13th 89 14th 95 80 15th 95 16th 78 17th ¹¹⁰⁰ 100 100 18th 98 19th 95 20th 85 21st 100 70 22nd 100 100 23rd 79 24th 90 70 25th 90 90 27th 85 30th 95 31st 95

Example 7

In vitro activity against Pseudomonas phaseolicola, the pathogen of bean plague

Malt agar (Biomaiz), after heat sterilization, was cooled to about 45 ° C and poured into plastic petri dishes, mixed with aqueous dilutions of the test compositions. After solidification of the medium, the Petri dishes containing the treated agar and untreated agar (control) were inoculated in the center with a suspension of the bean disease agent Pseudomonas phaseolicola. The dishes were then stored at 22 ° C. After 2.5 weeks, the diameter of the grown bacterial colonies was measured. As preparations, two replicate experiments were performed and the bacterial inhibitory activity was averaged as follows:

ififi ^- Growth in diameter of treated plant, 100_ =% inhibitory effect.

Increase in diameter in untreated plants

The active compounds of the invention were used as a 20% spray powder.

In the preparation % effect at 250 ppm compound different concentrations number 12th 62 15th 73 21st 64 24th 66

Example 8

Refrigeration against Helminthosporium teres in barley, greenhouse

About 20 pots containing the budding barley seedlings * were treated with the compositions of the invention to dripping moisture. Two pots implanted with barley were used as controls. The transesterification treatment was carried out at a concentration of 0.1% by weight. Three vessels were used as tested formulations and all were sprayed with a conidium suspension of Helminthosporium teres, a pathogen of wet stain. The conidium suspension was made with an aqueous solution containing 0.05% sodium oleate and 0.02% gelatin at a concentration of 100,000 spores / ml. After spore application, the three vessels were sealed in polyethylene bags and stored in a greenhouse at a temperature of about 20 ° C. The bags were then opened by cutting them at the height of the leaf tip. After 8 days, the number of wet spots per dish was determined. From this, the fungicidal activity was calculated according to the following formula:

100- ^Ned number y ^and stains the treated barley. 100 _ « _Qg Number of wet spots on untreated barley effect

The active ingredients of the present invention were used as a 20% spray.

Serial number of chemical compound in the preparation %-ancestor effect Second 100 Third 100 4, 99 10th 100 13th comparative material 1- (4-chloro-phenoxy) -3,3-dimethyl- 85 -141,2,4-triazol-1-yl) butanone. 86

Example 9

Systematic effect on pre-emergence soil treatment against sugar beet-powdery mildew Erysiphe polygoni in a greenhouse

After the sugar beet was planted, the seed pot was sprayed with 0.3 kg of active ingredient per hectare and kept in a greenhouse at 20 ° C with untreated pots. After emergence of the plants (12, 14 / dish), the plants were allowed to sprout the first two foliage leaves and then inoculated with the dry spores of Erysiphe polygonia, a pathogen of true beet powdery mildew. After three weeks (6 weeks after soil treatment), leaf contamination was evaluated. The fungicidal effect could only be obtained by uptake of the active compounds from the soil and evaluated as follows:

100 ~ ^{Infection on} treated plants. 100

Infection on untreated plants natas.

The active compounds of the present invention were used as a 20% spray powder. All Treatment Concentrations or Substances were tolerated by the plants and resulted in stronger, more bulky growth compared to untreated controls.

Serial number of compound in the preparation %-ancestor effect 12th 100 13th 100 14th 100

Example 10

Soya and wheat were sprayed with 25% w / w emulsion concentrates of test compounds prior to hatching. The application rate was 2 kg of active ingredient / ha. The plants were then kept in a greenhouse and the experiment evaluated after three weeks. The table below shows the% growth inhibition measured.

Serial number of compound in the preparation Growth inhibition (%) soy wheat Second 39 28 Third 22 28 7th 17 7 9th 0 17 13th 4 14 14th 17 24 18th 13 14 19th 4 14 22nd 65 21 23rd 30 17 25th 35 24 26th 35 24 comparative material 2-chloroethyl trimctil- ammonium chloride 0 17th

It can be seen from the above table that the compositions of the invention are generally more effective than the comparator.

Example 11

Rice plants were treated with a 25% w / w emulsion concentrate prior to emergence at a dose of 2 kg active ingredient / ha. The plants were kept in a greenhouse for three weeks, and growth inhibition was evaluated. The following table gives the values obtained:

Serial Inhibition Serial Inhibition Serial Number (%)

22/11/11

25.7

26, _14

Reference substance

2-Chloroethyl trimethylammonium chloride 0

In the experiment, the comparator did not show growth inhibitory activity of the compositions of the invention.

Example 12

Sugar beet plants were sprayed with a 25% w / w emulsion concentrate prior to emergence at a dose of 2 kg of active ingredient / ha. After growing for three weeks in a greenhouse, the percent growth inhibition values and the coloration of the plants were determined. The results are shown in the table below:

The compound in the composition Plant Inhibition (%) coloring Treaty * First 9 1 Third 34 1 7th 34 0 8th 37 0 9th 25 1 10 37 0 12 22 0 13 41 0 14 41 0 16 53 0 17 53 0 18 22 1 19th 37 0 20 37 1 21 6 1 22 37 1 23 53 2 25 69 2 26 37 2

comparative material

2-Chloroethyl trimethylammonium chloride 0 0 • = Evaluation of coloration:

= same control = intense green = dark green.

It can be seen from the table that the compositions of the invention a. affect beet growth, which was not available with the comparator.

189,649

Example 13

Effect of Preventive Leaf Treatment on Pennisetum galucum Leaf Pathogen, Fusarium culmorum, in a Greenhouse

Young Pennisetum glaucum plants, beginning with a second leaf state (about 30 per dish), were sprayed at drip irrigation at the concentrations indicated in the table below. After drying, the treated and untreated control plants were sprayed with a conidium suspension of Fusarium culmorum and placed in a humidified greenhouse at about 22 ° C. After 4 days, the percentage of infected leaf areas was determined. The fungicidal effect was calculated from the following equation:

100 'θθ - infection in treated plants _

Infection in untreated plants effect.

The active compounds of the present invention were used as a 20% spray powder.

100 _ 10θ infection in treated plants Infection in untreated plants% effect.

The active compounds of the present invention were used in the form of a 20% spray powder.

The compound number in the composition has a% effect of 500 ppm to 100 ppm

The compound number in the formulation is a% effect

500 ppm 100 ppm

Second 100 100 Third 91 9th 80 12th 90 13th 100 14th 100 16th 95 17th 95 18th 95 19th 90 20th 80 22nd 99 90 23rd 100 99 24th 100 97 25th 100 98 26th 98 93 27th 90 29th 97 90 30th 97 90 31st 100 98

100 100 1. 93 1 93 13th 100 14th 93 16th 100 17th 87 19th 93 20th 87 21st 100 96 22nd 100 100 23rd 100 100 21st 100 100 25th 96 96 26th 100 96 27th 98 98 28th 100 98 29th 100 98 33rd 100 100 31st 100 100

Example 15

The effect of seed treatment on Helminthosporium sativum, the causative agent of dry barley disease

Barley seed infected with Helminthosporium sativum was treated with an amount of 50 mg of active ingredient per 100 g of seed. In the case of miniature, 2 g of the treated seed and 2 g of the untreated seed were placed in dishes in a total of two replicates and incubated at 15 ° C in a climate chamber. Artificial illumination was applied over 12-hour periods from the time the plants emerged. After four weeks, the percentage of plants infected with dry disease was determined. In the case of untreated seeds, all plants were infected.

Example 14

Effect of Preventive Leaf Treatment on Carbospora beticola, a pathogen of beet leaf spot in greenhouse

At least two well-developed leafy sugar beet plants were sprayed with a spray concentration of the following table. After permedé has dried, the treated plants and untreated control plants were sprayed Cercospora beticola conidia suspension of _fe and in wet conditions were incubated for two days at 26 C in a greenhouse. The plants were then grown under normal heat lyase conditions. Two weeks after treatment,% infection values were determined.

The tungicidal effect was calculated according to the following formula:

Serial number of compound in the preparation %-ancestor effect 2, 100 Third 99.5 4th 100 5th 99.5

The active compounds of the present invention were used in the form of a 20% spray powder.

Example 16

Effect of seed treatment on seeded Phoma betae in sugar beet

Sugar beet seed contaminated with Phoma betae was treated with a preparation of 250 mg active ingredient / 100 g dose. Treated and untreated seed10

Four to four of the 101 were seeded into 25-25 seedlings in pots and kept in a climate chamber at 15 ° C. The plants were exposed to artificial light for 12 hours after emergence. Until the end of the experiment, which lasted a total of seven weeks, the infected plants were counted weekly and removed. In untreated controls, a total of 76.1% of the emerged plants were infected. The protective effect of the treatment was calculated according to the following formula:

inn Infection in treated plants. 100 ™ Infection in untreated plants

The active compounds of the present invention were applied in a spray volume of 20%.

Serial number of compound in the preparation %-ancestor effect Second 100 Third 97 4th 97 5th 100 6th 83 12th 92 13th 99 14th 96

comparative material

O- (1,1'-Biphenyl-4-yloxy) -o (1,1-dimethylethyl) -yl-1,2,4-thiazole-1-ethanol 51

- (4-Chlorophenoxy) -3,3-dimethyl-1- (1,2,4-triazol-1-yl) -2-butanone 57

Claims (60)

PATENT CLAIMS A fungicide, a plant growth regulator and a bacterial agent comprising 90 to 10% by weight of a solid or liquid carrier, preferably kaolin, silica, clay, cellulose, cyclohexanone or xylene, up to 20% by weight of a surfactant, preferably lignin sulfonic acid. calcium salt, alkylphenyl poly (glycol ether), sodium salt of N-methyl-N-oleyl taurine, nonylphenyl polyoxyethylene or calcium dodecylbenzene sulfonate, the active ingredient is 10-90% by weight of Optionally in the form of an acid addition salt thereof, preferably with nitric acid, of the formula (I) R is phenyl optionally substituted on one or more times with C 1 -C 4 alkyl or with halogen atoms, and R 1 is C 1 -C 10 alkyl or C 3 -C 6 alkenyl. The fungicidal and plant growth controlling composition according to claim 1, wherein the active ingredient is isopropyl-2-phenyl-3- (1,2,4-triazol-1-yl) -propionitrile. HN0 ₃ . The fungicidal and plant growth controlling composition of claim 1, wherein the active ingredient is 2-isopropoxy-2-phenyl-3- (1,2,4-triazol-1-yl) -propionitrile. Fungicide and plant growth regulator according to Claim 1, characterized in that the active ingredient is 2- (hexyloxy) -2- (2-methylphenyl)) - 3- (1,2,4-triazole-1). yl) -propionitrile HNO ₃ . The fungicidal composition of claim 1, wherein the active ingredient is 2-butoxy-2- (2-methylphenyl) -3- (1,2,4-triazol-1-yl) propionyltril. The fungicidal composition according to claim 1, wherein the active ingredient is 2-butoxy-2- (2-methylphenyl) -3- (1,2,4-triazol-1-yl) -propionitrile HNO _S. The fungicidal composition of claim 1, wherein the active ingredient is 2- (hexyloxy) -24 / 2-methylphenyl) -1,2,4-triazol-1-yl) propionitrile. The fungicidal and plant growth regulating composition of claim 1, wherein the active ingredient is 2-butoxy-2-phenyl 3- (1,2,4-triazol-1-yl) -propionitrile. HNO ₃ . The fungicidal and plant growth controlling composition of claim 1, wherein the active ingredient is 2-butoxy-2- (2-chlorophenyl) -3- (1,2,4-triazol-1-yl) propionitrile. hnoj. IC. The fungicidal and plant growth regulating composition of claim 1, wherein the active ingredient is 2-ethoxy-2-phenyl-3- (1,2,4-triazol-1-yl) -propionitrile. HN0 ₃ . The fungicidal and plant growth controlling composition according to claim 1, wherein the active ingredient is 2-phenyl-2-propoxy-2- (1,2,4-triazol-1-yl) -propionitrile. HN0 ₃ . 12. The fungicidal composition according to claim 1, wherein the active ingredient is 2- (3-chlorophenyl) -2-hexyloxy-3- (1,2,4-triazol-1-yl) propionitrile HNO. ₃ . 13. A bactericidal, fungicidal, plant growth controlling composition according to claim 1, wherein the active ingredient is 2-butoxy-2-phenyl-3- (1,2,4-triazol-1-yl) -propionitrile. The fungicidal and plant growth regulating composition of claim 1, wherein the active ingredient is 2-phenyl-2-propoxy-3- (1,2,4-triazol-1-yl) -propionitrile. 15. The fungicidal and plant growth controlling composition of claim 1, wherein the active ingredient is 2-ethoxy-2-phenyl-3 - [(1,2,4) -triazol-1-yl) -propionitrile. 15. Fungicidal and bactericidal composition according to claim 1, characterized in that the active substance 2- (hexyloxy) -2-phenyl-3- (l, 2,4-triazol-1-ylidene-propionitrile. Hn0 _third The fungicidal and plant growth regulating composition of claim 1, wherein the active ingredient is 2- (allyloxy) -2-phenyl-3- (1,2,4-triazol-1-yl) propionitrile. HN0 ₃ . The fungicidal and plant growth controlling composition of claim 1, wherein the active ingredient is 2-butoxy-2- (4-chlorophenyl) -3- (1,2,4-triazol-1-yl) propionitrile. . HN0 ₃ . The fungicidal and plant growth regulating composition of claim 1, wherein the active ingredient is 2- (allyloxy) -2-phenyl-3- (1,2,4-triazol-1-yl) propionitrile. 20. The fungicidal and plant growth controlling composition according to claim 1, wherein the active ingredient is 2-methoxy-2-phenyl-3 (1,2,4-triazol-1-yl) -propionitrile. The fungicidal and plant growth controlling composition of claim 1, further comprising -111, characterized in that the active ingredient is 2- (hexyloxy) -2-phenyl-3- (1,2,4-triazol-1-yl) propionitrile. 22. The fungicidal composition of claim 1, wherein the active ingredient is 2- (2-chlorophenyl) -2- (hexyloxy) -3- (1,2,4-triazol-1-yl). > propionitrile.HNO ₃ . 23. A fungicidal and plant growth controlling composition according to claim 1, wherein the active ingredient is 2- (2-chlorophenyl) -2-propoxy-3- (1,2,4-triazol-1-yl) -. propionitrile. HNO ₃ . 24. The fungicidal and plant growth regulating composition of claim 1, wherein the active ingredient is 2 - (4-chlorophenyl) -2-pTopoxy-3- (1,2,4-triazol-1-yl) propionitrile. HNO ₃ . 25. The fungicidal composition of claim 1, wherein the active ingredient is 2- (4-chlorophenyl) -2- (hexyloxy) -3- (1,2,4-triazol-1-yl) propionitrile. hno ₃ . 26. The fungicidal and plant growth controlling composition according to claim 1, wherein the active ingredient is 2- (4-chlorophenyl) -2-propyloxy-3- (1,2,4-triazol-1-yl). propionitrile. 27. The fungicidal and plant growth controlling composition of claim 1, wherein the active ingredient is 2-butoxy-2- (4-chlorophenyl) -3- (1,2,4-triazol-1-yl) propionitrile. . 28. The fungicidal composition of claim 1, wherein the active ingredient is 2- (2-methylphenyl) -2-octyloxy-3- (1,2,4-triazol-1-yl). -propionitrile. HNO ₃ . 29. The fungicidal composition according to claim 1, wherein the active ingredient is 2-dexyloxy-2- (2-methylphenyl) -3- (1,2,4-triazol-1-yl) propionitrile. HNO ₃ . 30. The fungicidal composition of claim 1, wherein the active ingredient is 2- (2-methylphenyl) -2-octyloxy-3- (1,2,4-triazol-1-yl) propionitrile. 31. The fungicidal composition of claim 1, wherein the active ingredient is 2 <2-chloro-R-phenyl) -2-butoxy-3- (1,2,4-triazol-1-yl) -propionitrile. 32. The fungicidal composition of claim 1, wherein the active ingredient is 2- (2-chlorophenyl) -2-propoxy-3- (1,2,4-triazol-1-yl) propionitrile. 33. The fungicidal composition of claim 1, wherein the active ingredient is 2-butoxy-2- (2,4-dichlorophenyl) -3- (1,2,4-thiazol-1-one). il) -propionitrile .HN0 ₃ . 34. The fungicidal composition of claim 1, wherein the active ingredient is 2-butoxy-2- (2,4-dichlorophenyl) -3- (1,2,4-triazol-1-yl). ) propionitrile. 35. The fungicidal composition of claim 1, wherein the active ingredient is 2- (allyloxy) -2- (2,4-dichlorophenyl) -3- (1,2,4-triazole). l-yl-propionitrile. 36. The fungicidal composition of claim 1, wherein the active ingredient is 2- (3,4-dichlorophenyl) -2-propoxy-3- (1,2,4-triazol-1-yl) propionitrile. HNO ₃ . The fungicidal composition according to claim 1, wherein the active ingredient is 2- (3,4-dichlorophenyl) -2-propoxy-3- (1,2,4-triazolyl) - propionitrile. 38. The fungicidal composition of claim 1 wherein the active ingredient is 2- (3,4-dichlorophenyl) -2-hexyloxy-3- (1,2,4-triazol-1-yl) propionitrile. . HN0 ₃ . 39. The fungicidal composition of claim 1, wherein the active ingredient is 2- (3,4-dichlorophenyl) -2-hexyloxy- (1,2,4-triazol-1-yl) propionitrile. The fungicidal composition of claim 1, wherein the active ingredient is 2- (4-fluorophenyl) -2-propoxy-3- (1,2,4-triazol-1-yl). propionitrile. HNO ₃ . 41. The fungicidal composition according to claim 1, wherein the active ingredient is 2β-fluorophenyl) -2-propoxy-3- (1,2,4-triazol-1-yl) propionitrile. 42. The fungicidal composition of claim 1, wherein the active ingredient is 2-butoxy-2- (4-fluorophenyl) -3- (1,2,4-triazol-1-yl) -ptopionitrile. . hno ₃ . 43. The fungicidal composition of claim 1, wherein the active ingredient is 2-butoxy-2- (4-fluorophenyl) -3- (1,2,4-triazol-1-yl) propionitrile. 44. The fungicidal composition of claim 1, wherein the active ingredient is 2- (2-fluorophenyl) -2-propoxy-3- (1,2,4-triazol-1). -il) -propionitrile. HN0 ₃ . 45. The fungicidal composition according to claim 1, wherein the active ingredient is 2/2-fluorophenyl) -2-propoxy-3- (1,2,4-triazol-1-yl) propionitrile. 46. The fungicidal composition according to claim 1, wherein the active ingredient is 2-butoxy-? - (2-Fluoro-phenyl) -3- (1,2,4-triazol-1-yl) -propionitrile. HN0 ₃ . 47. The fungicidal composition of claim 1, wherein the active ingredient is 2-butoxy-7- (2-fluorophenyl) -3- (1,2,4-triazol-1-yl) propionitrile. . 48. The fungicidal composition of claim 1, wherein the active ingredient is 2- (2-fluorophenyl) -2- (hexyloxy) -3- (1,2,4-triazole). -1-yl) -propionitrile. EN0 ₃ . 49. The fungicidal composition of claim 1, wherein the active ingredient is 2- (2-fluorophenyl) -2- (hexyloxy) -3- (1,2,4-triazol-1-yl) propionitrile. . 50. The fungicidal composition of claim 1, wherein the active ingredient is 2- (4-bromophenyl) -2-propoxy-3- (1,2,4-triazol-1-yl) -. propionitrile. HN0 ₃ . 51. The fungicidal composition of claim 1, wherein the active ingredient is 2- (4-bromo-enyl) -2-propoxy-3- (1,2,4-triazol-1-yl). propionitrile. 52. The fungicidal composition of claim 1, wherein the active ingredient is 2- (4-bromo-phenyl) -2-hexyloxy-3- (1,2,4-triazol-1-yl) -propionitrile. HN0 ₃ . 53. The fungicidal composition of claim 1, wherein the active ingredient is 2- (4-bromophenyl) -2-hexyloxy-3- (1,2,4-triazol-1-yl). propionitrile. 54. The fungicidal composition according to claim 1, wherein the active ingredient is 2- (2,4-dichlorophenyl) -2-propoxy-3- (1,2,4-triazol-1-yl) propionitrile. HN0 ₃ . 55. The fungicidal composition of claim 1, wherein the active ingredient is 2- (2,4-dichlorophenyl) -2-propoxy-3- (1,2,4-triazol-1-yl). propionitrile. 56. The fungicidal composition of claim 1, wherein the active ingredient is 2- (2-methylphenyl) -2- (pentyloxy) -3- (1,2,4-triazol-1-yl). ) -proplonitrile. HN0 ₃ . 57. The fungicidal composition according to claim 1, wherein the active ingredient is 2- (2-methyl12). -121 189,649 phenyl) -2- (pentyloxy) -3- (1,2,4-thiazol-1-yl) propionitrile. 58. The fungicidal composition of claim 1, wherein 2- (4-methylphenyl) -2-5-propoxy-3- (1,2,4-triazol-1-yl) -propionitrile. HNO ₃ . 59. The fungicidal composition according to claim I, wherein the active ingredient is 2- (hexyloxy) -2- (4-methylethylphenyl) -3- (1,2,4-triazole-1-). yl) -propionitril.HNOj. _1Q 60. The compound according to claim 1, prizes ^u! Its active ingredient is 2- (4-methylphenyl) -2-propoxy-3- (1,2,4-triazol-1-yl) propionitrile. 61. The fungicidal composition of claim 1, wherein the active ingredient is 2- (hexyloxy) -244-methylphenyl) -3- (1,2,4-triazol-1-yl). -propionites- -j 5 ril. 62. The fungicidal composition of claim 1, wherein the active ingredient is 2-butoxy-2- (4-methylphenyl) -3- (1,2,4-triazol-1-yl) propionitrile. . 63. A process for the preparation of 1,2,4-triazol-1-yl-propionitrile derivatives and acid addition salts thereof, preferably with nitric acid, of the formula (I) R is phenyl optionally substituted on one or more times with C 1 -C 4 alkyl or with halogen atoms, and R 1 is C 1 -C 10 alkyl, C 3 -C 6 alkenyl, wherein the compound of formula II is a solvent with 1,2,4-triazole or its alkali compound and optionally a base in the presence of K and Rj are as defined above and Y represents an alkylsulfonyloxy group and optionally forms an acid addition salt.