FR2525596A1 - (TRIAZOLE-1,2,3 YL-1) -PROPIONONITRILES, PROCESS FOR THEIR PREPARATION AND BIOCIDAL PRODUCTS CONTAINING SUCH COMPOUNDS - Google Patents

Abstract

THE INVENTION RELATES TO NEW (TRIAZOLE-1,2,4 YL-1) -PROPIONONITRILES. THESE COMPLY WITH THE FORMULA: (CF DRAWING IN BOPI) IN WHICH R REPRESENTS AN AROMATIC HYDROCARBON RADICAL POSSIBLY CARRYING A SUBSTITUTE OR SEVERAL SUBSTITUENTS, IDENTICAL OR DIFFERENT, TAKEN IN THE WHOLE CONSTITUTED BY THE HALOGENES AND THE ALKYLES , ALCOXY, ALKYLTHIO, TRIFLUOROMETHYL AND NITRO AND R REPRESENTS AN ALKYL, ALCENYL OR ALCYNYL RADICAL OR A PHENYLALKYL RADICAL POSSIBLY CARRIER OF A SUBSTITUTE OR OF SEVERAL SUBSTITUENTS, IDENTIALS AND DIFFERENT ALKYL, ALCENYL OR ALCYNYL , ALCOXY, ALKYLTHIO, TRIFLUOROMETHYL AND NITRO. THE INVENTION ALSO INCLUDES THE ADDITIONAL SALTS THAT THESE COMPOUNDS FORM WITH MINERAL OR ORGANIC ACIDS. THESE TRIAZOLYL -PROPIONONITRILES, BECAUSE OF THEIR INTERESTING BIOCIDAL PROPERTIES, MAY CONSTITUTE THE ACTIVE SUBSTANCES OF PHYTOSANITARY PRODUCTS USEABLE, AMONG OTHERS, AS FUNGICIDES, AS GROWTH REGULATORS AND AS BACTERICIDES.

Description

2525 q 96

  The present invention relates to novel (triazole

  1,2,4-yl-1) -propionitrile, a process for their preparation, and biocidal products containing such compounds,

  more particularly products with action foncigicide.

  Imidazolylpropionitrile is already known from

  fungicidal action (see the first published leaflet

  However, these compounds have a relatively narrow range of activity, which is unsatisfactory.

  It was therefore necessary to find - this was the technical problem

  new propionitriles which open up a wide range of application possibilities, particularly in the field of plant protection, and which have a

broad fungicidal action fields.

  This technical problem is solved, according to the invention, by imidazolyl propiononitriles corresponding to the general formula:

0 R 1

R C CH 2 N I

in which:

  R represents an aromatic hydrocarbon radical which may be

  carrying one or more substitute

  identical or different radicals selected from the group consisting of halogens, C 1 -C 4 alkyls, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, trifluoromethyl radical and nitro radical; and R 1 is C1-C10 alkyl, C3-C8 alkenyl,

  C 3 -C 8 alkynyl or a phenylalkyl radical,

  with one or more substituents

  substituents, identical or different, taken in

  It seems to consist of halogens, C 1 -C 4 alkyls, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, trifluoromethyl and nitro radicals, as well as the addition salts they form with

mineral or organic acids.

  The compounds according to the invention have an action

  biocide in the broadest sense of the term, but they are

  especially fungicidal action: on this point they surpass, against all odds,

  known active persons who have a similar constitution and who

feel in the same direction.

  Surprisingly, the fungicidal action is exercised against

  fungi occupying very diverse taxonomic positions.

  When the compounds of the invention are used for the treatment of aerial parts of plants they protect

  these against pathogens carried by the wind.

  They can be used for the disinfection of the seeds when one wants to fight against the pathogens carried by them They have moreover a systemic effect: in other words, they are absorbed by the roots of the plants, for example when they have been introduced during sowing, they are transported in the aerial parts of plants and they

  protect them against pathogens.

  Other effects observed include:

  Regulatory action on growth and bactericidal action.

  Due to the wide range of activity of the present compounds they are suitable not only for the protection of cultivated plants but also for the protection of materials and for the control of pathogenic microbes for humans or animals. so to say they have a

  wide range of application possibilities.

  According to the particular significance of each

  their substituents the compounds will stand out more particularly

  In this or that field of application

  that they can be used as fungicides, as

  plant growth promoters or as bactericides.

  In the compounds represented by the general formula (I), the symbols R and R 1 will have, for example, the following meanings: R: 2-fluoro-phenyl, 3-fluoro-phenyl, 4-fluoro-phenyl, 2-chlorophenyl, chloro Phenyl, 4-chlorophenyl, 2-bromo-phenyl, 3-bromo-phenyl, 4-bromo phenyl,

  2-iodo-phenyl, 3-iodo-phenyl, 4-iodo-phenyl, dichlo-

  2,4-phenyl phenyl, 3,4-dichlorophenyl, 2,6-dichlorophenyl

  Nyl, 1-methyl-2-phenyl, 3-methylphenyl, 4-methylphenyl

  Nyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2-propylphenyl, 3-propylphenyl, 4-propylphenyl, 2-isopropylphenyl, 3-isopropylphenyl, 4-isopropyl

  phenyl, butyl-2-phenyl, butyl-3-phenyl, butyl-4-phenyl

  nyl, sec-butyl-2-phenyl, sec-butyl-3-phenyl,

  4-butylphenyl, 2-tert-butylphenyl, tert-butyl-3-phenyl

  Nyl, 4-tert-butylphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2-ethoxyphenyl, 3-ethoxy

  phenyl, 4-ethoxyphenyl, 2-methylthiophenyl, methyl-

  3-thio-phenyl, 4-methylthiophenyl, 2-ethylthiophenyl, 3-ethylthiophenyl, 4-ethylthiophenyl, 2-trifluoromethyl

  phenyl, trifluoromethyl-3-phenyl, trifluoromethyl-4-folded

  Nyl, 2-nitro-phenyl, 3-nitro-phenyl, 4-nitro-phenyl, 3-fluoro-4-methoxyphenyl, 3-chloro-5-nitro-phenyl, 4-chloro-2-fluoro-phenyl, 3,4,5-trimethoxy phenyl or 5-chloro-2-nitro-phenyl, and R: as C 1 -C 11 alkyl for example methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl,

  decyl, isopropyl, 2,2-dimethyl propyl or 1-methyl-dimethyl

  2,2-thylpropyl; as C 3 -C 8 alkenyl, for example

  butene-2-yl, methyl-3-butene-2-yl, hexenyl, heptane

  nyl or octenyl; as phenylalkyl, for example benzyl, fluoro-2-benzyl, 3-fluoro-benzyl, 4-fluoro-benzyl, 2-chlorobenzyl, 3-chlorobenzyl, 4-chlorobenzyl, 2-bromo-benzyl, 3-bromo-benzyl, bromo-2-benzyl, 4 benzyl, 2,4-dichlorobenzyl, 2,6-dichlorobenzyl, 3,4-dichlorobenzyl, 2-methylbenzyl, 3-methylbenzyl, 4-methylbenzyl, 2-nitrobenzyl, 3-nitrobenzyl, nitro -4 benzyl,

  2-trifluoromethylbenzyl, 3-trifluoromethylbenzyl, tri-

  4-fluoromethyl benzyl, 2-methoxy benzyl, 3-methoxy benzyl

  zyl, 4-methoxybenzyl, 2-ethoxybenzyl, 3-ethoxybenzyl, 4-ethoxybenzyl, 2-propoxybenzyl, 3-propoxybenzyl, 4-propoxybenzyl, butoxybenzyl, 3-butoxybenzyl,

  4-butoxybenzyl, 2-methylthiobenzyl, 3-methylthio benzene

  zyl, 4-methylthiobenzyl, 2-ethylthiobenzyl, ethyl-

  3-thio-benzyl, 4-ethylthio-benzyl, 2-butylthio-benzyl,

  butylthio-3 benzyl or 4-butylthio benzyl.

  As mineral or organic acids for training

  addition salts, for example, haloic acids may be mentioned;

  such as hydrochloric acid and hydrobromic acid

  that also phosphoric acid, sulfuric acid, more particularly nitric acid, monofunctional or bifunctional carboxylic and hydroxycarboxylic acids, for example acetic acid, maleic acid, succinic acid,

  fumaric acid, tartaric acid, citric acid,

  salicylic acid, sorbic acid or lactic acid, and

  sulphonic acids, for example p-toluene

  sulfonic acid and 1,5-naphthalene disulfonic acid.

  These acid addition salts can be prepared by

  the usual salification methods, for example by dissolving

  lution of a compound of formula (I) in an appropriate solvent

and adding the acid.

  Some of the compounds in accordance with the inventionse

  These are in particular those in formula (I) of which: R represents a phenyl, 2-chlorophenyl or 3-chloro radical;

  phenyl, 4-chlorophenyl, 2,4-dichlorophenyl, dichlo-

  3,4-phenyl, 4-bromo-phenyl, 2-fluoro-phenyl, 4-fluoro-phenyl or 2-methylphenyl, and

  R 1 represents an ethyl, allyl, propyl or isopropyl radical;

  pyl, butyl or hexyl, and among these compounds are preferred those in which: R represents a phenyl, 4-chlorophenyl or 2-methylphenyl radical and

  R 1 represents a propyl, isopropyl or butyl radical.

  Very effective are the compounds of the invention

  2-isopropoxy-2-phenyl-1,2,4-triazol-1-propiononitrile, hydronitrate,

  butoxy-2 (2-methyl-phenyl) -2 (1,2,4-triazole-1-yl) -3

  piononitrile, hydronitrate, 2-phenylpropoxy-2 (1,2,4-triazolyl) propiononitrile, hydronitrate,

  2-butoxy-4-chlorophenyl-2-triazol-1,2,4-yl-3-one

  piononitrile, hydronitrate, 2- (4-chlorophenyl) -propoxy-2-triazole-1,2,4-yl-3-propiononitrile, hydronitrate,

  2-isopropoxy-2-phenyl-1,2,4-triazol-1-ylpropionitrile

Trile,

  butoxy-2 (2-methyl-phenyl) -2 (1,2,4-triazole-1-yl) -proton

  piononitrile, 2-hexyloxy-2-phenyl-1,2,4-triazol-1-propiononitrile, hydronitrate,

  2-butoxy-2- (4-chlorophenyl) -2,4-triazolyl-3-yl

  piononitrile, 2- (4-chlorophenyl) -2-propyloxy-1,2,4-triazol-1-yl) propiononitrile,

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

  piononitrile, hydronitrate, 2-butoxy-2-phenyl-1,2,4-triazole-1-propiononitrile, hydronitrate,

  2-butoxy (2-chloro-phenyl) -2 (1,2,4-triazole-1-yl) -3

  piononitrile, hydronitrate, 2-ethoxy-2-phenyl-2-triazol-1,2,4-yl-1-propiononitrile, hydronitrate, 2-allyloxy-2-phenyl-1,2,4-triazol-1-yl) Propionitrile, hydronitrate,

  2- (2-chloro-2-phenyl) -2-propoxy (1,2,4-triazol-1-yl) -propane

  piononitrile, hydronitrate, 2- (2-chlorophenyl) -2-hexyloxy (1,2,4-triazole-1-yl) propiononitrile, hydronitrate,

  2-hexyloxy-2-methyl-phenyl-2 (1,2,4-triazole-1-yl) -proton

  piononitrile, butoxy-2-phenyl-2 (1,2,4-triazole-1-yl) propiononitrile,

  2- (2-chlorophenyl) -2-butoxy- (1,2,4-triazole-1-yl) -propane

  piononitrile, 2-ethoxy-2-phenyl-2-triazole-1,2,4-yl-1-propiononitrile, 2-allyloxy-2-phenyl-1,2,4-triazol-1-ylpropiononitrile, and

  2-chloro-phenyl-2-propoxy-1,2,4-triazol-1-yl

  piononitrile The compounds according to the invention have mainly fungicidal effects but they are indicated at the same time, on

  a whole series of cultivated plants, by regular effects

on growth.

  Depending on the nature of the plant and depending on the dose

  applied can also obtain herbicidal effects.

  The compounds according to the invention, because they

  both qualitatively and quantitatively

  on plants as metabolic changes

  of these, should be placed in the category of

  growth factors, products which are indicated by the pos-

  following application options: Inhibition of vegetative development in the case of woody or herbaceous plants, for example on roadsides, on railway installations, etc., in

  the aim of avoiding the appearance of exuberant vegetation.

  Inhibition of growth, in the case of cereals to prevent lodging or breaking of stems, in the case of

cotton to increase yield.

  Action on the branching of vegetative and general organs

  in the case of ornamental plants or

  cultivation in order to increase the number of flowers

  or, in the case of tobacco and tomato, for the purpose of

  to prevent the formation of lateral discharges.

  Improvement of the quality of the products, for example

  the sugar content in the case of sugar cane

  sugar, sugar beet or fruit, and uniform

  maturation of the products at the time of

  harvest, which leads to higher yields.

  Increased resistance to climatic agents, such as

than cold and drought.

  Action on the latex flow in the case of rubber plants

  Chouc. Parthenocarpic fruit formation, pollen sterility and action on sex are other possibilities of application. Action on seed germination or on budding. Defoliation or action on the abscission of fruits in the

purpose of facilitating the harvest.

  The compounds according to the invention are suitable

  especially to influence the development of

  but they also act as good regula-

  growers on cereals, soybeans and cotton.

  Depending on the intended purpose, the dose to be applied will generally range from 0.05 to 5 kg ai / ha, although

higher doses.

  The timing of application depends on the purpose of the treatment

and climatic conditions.

  Surprisingly, the compounds according to the invention have a more extensive and intense activity than that of

  known products acting in the same direction.

  In addition to the actions discussed above the compounds according to the invention also deploy a

  bactericidal action which opens up possibilities for

additional information.

  The compounds according to the invention can be used

  alone, mixed with each other or mixed with other active ingredients Depending on the purpose you wish to achieve

  can add other plant protection products or

  parasitic. It is good to apply the active ingredients defined herein, or-their mixtures, in the form of compositions, such as

  that powders, spreading agents, granules, solu-

  tions, emulsions or suspensions, containing

  or liquid and / or solid diluents and possibly wet

  lants, adhesives, emulsifiers and / or dispersants.

  Suitable liquid carriers include, for example,

  water, aliphatic or aromatic hydrocarbons, such as

  benzene, toluene and xylenes, as well as cyclo-

  hexanone, isophorone, dimethylsulfoxide, dimethylformat

  mide, and also fractions of mineral oils and

vegetal oils.

  The solid supports may be mineral soils, such as Tonsil, silica gel, talc, kaolin,

  attapulgite, limestone and silica, or vegetable products

rates, such as flours.

  Examples of surfactants are lignin

  calcium sulphonate, polyalkoxylation products of alkyl-

  phenols, naphthalenesulfonic acids and their salts, condensation products of formaldehyde, sulfates of fatty alcohols as well as substituted benzenesulphonic acids and their salts.

  When the active ingredients are to be used for disin-

  seed fodder can also be added dyes to give the treated seed a clear color

visible.

  The proportion of the active ingredient (s) in the

  various formulations may vary in extended intervals.

  Thus products may contain, for example,

  about 10 to 90% by weight of active materials, from about 90 to 10% by weight of liquid or solid carriers and optionally

  up to 20% by weight of surfactants.

  The spreading of the products can be done in the usual way, for example with water as a support in the form of slurries that are sprayed at doses of about 100 to 1000 liters / hectare It is also possible to apply the products by the so-called "low volume" process and the process

  said "at very low volume", as well as in the form of micro-

aranulés.

  To prepare the compositions, for example,

  The following constituents are: Wettable powders (slurry powders) a) 40% by weight of active ingredient% by weight of clay minerals% by weight of silica 10% by weight of pitch from the treatment of cellulose% by weight of surfactants based on a mixture of lignin sulphonic acid calcic salt and alkylphenol polyethoxylation products; b) 25% in% in% in weight by weight weight in weight c) 10% in weight% in weight 15% in weight% in weight% in weight B Pate% in% in% in 2% in% in 23% in weight weight weight weight weight weight of active ingredient of silica kaolin

  of surfactants based on the sodium salt of N

  methyl N -oleyl taurine and calcium salt of lignin sulfonic acid; of active ingredient of cellulosic pitch silica clay minerals

  of surfactants based on the sodium salt of N

  methyl-N-olethyl-taurine and calcium salt of

lignin-sulfonic acid.

  of active ingredient of a sodium alumino-silicate of a cetylpolyglycolic ether with 8 moles of polyethylene glycol pin oil ethylene oxide. C Emulsifiable concentrate% by weight of active ingredient% by weight of cyclohexanone% by weight of xylene% by weight of a mixture of a poly-ethoxylation product of nonylphenol and of dodecylbenzenesulfonate

of calcium.

  For preparing the novel compounds which are the subject of the present invention, it is possible, for example, to react propiononitriles corresponding to the general formula (II):

O R 1

I 1

E CH 2 Y (II)

1 CN

  in which R and R have the meanings indicated above I and Y represents a halogen or an arylsulfonyloxy radical or

  optionally halogenated alkylsulphonyloxy in the side chain

  with 1,2,4-triazole, which corresponds to the formula:

N CH

He He

HC N

\ / NOT

H

  or one of its alkali metal derivatives, in the presence of a

  solvent and optionally in the presence of a base.

  The halogen is, for example, chlorine, bromine or iodine. The alkylsulphonyloxy radical is, for example, a methyl-, ethyl-, propyl and trifluoromethylsulphonyloxy radical, and the

  arylsulphonyloxy radical is, for example, a benzenesulphonyl radical.

fonyloxy or p-toluenesulfonyloxy.

  The reaction can be carried out both by using an excess of 1,2,4-triazole, optionally in the presence of a

  solvent, by adding a strong base, for example hydro-

  Sodium hydroxide or potassium hydroxide 1,2,4-triazole may be further substituted for one of its alkali metal derivatives. Suitable solvents are in particular solvents inert with respect to the reaction partners, preferably

  polar aprotic solvents, such as N, N-

  dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidine

  lidone, tetramethylurea, hexamethylphosphorotriamide and benzonitrile, but also higher boiling aliphatic and arcoatic hydrocarbons such as toluene,

chlorobenzene and xylenes.

  The reaction temperature can vary over extended intervals. It will preferably be between 200 ° C. and 200 ° C. The reactions are carried out under pressure.

normal or under high pressure.

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

  the invention are generally solid bodies almost

  lores and odorless Their acid addition salts are

  crystallized poses, also colorless and odorless 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, N, N-dimethylformamide,

  lower alcohols, chloroform and methyl chloride.

  lene. The following examples illustrate the preparation of

compounds according to the invention.

EXAMPLE 1

  2-Isopropoxy-2-phenyl-2-triazole-1-yl-1-propiononitrile hydronitrate (compound N 2) to a suspension of sodium hydride (0.55 mole) dissolved in 50 ml of dimethylformamide (DMF) 0.55 mol of 1,2,4-triazole is then added with stirring and cooling. 0.11 mol of 2-isopropoxy-3-methylsulphonyloxy-2-phenylpropionitrile is then added to 50 ml of DMF and The mixture is kept for 1 hour and a half at a temperature of the C bath. After cooling, it is extracted 3 times with 100 ml of ether, the combined ethereal phases are washed twice with water and dried over MgSO 4. Under reduced pressure, 50 ml of isopropanol are added to the residue and 6.8 ml of concentrated nitric acid are added dropwise with stirring and cooling. ether is stirred for another quarter of an hour and then squeezed On

  recrystallizes the product in isopropanol.

  Melting point: F 185-189 C (with decomposition).

  Quantity collected: 15 g, a yield of 43%.

EXAMPLE 2

  2-Isopropoxy-2-phenyl-2-triazol-1-ylpropionitrile (compound N 3)

  10 g of isopropyl hydrate is dissolved in methanol.

  2-Propoxy-2-phenyl-2-triazol-1, 4-ylpropionitrile and 8 ml of 32% ammonia water are added to the solution. The mixture is poured into water and extracted with water. ethyl acetate,

  it is dried over MgSO 4, the ethyl acetate is evaporated off.

  Under a reduced pressure, a little ethyl acetate and activated charcoal are added and the mixture boiled for a short period of time.

  moment, squeeze and evaporate again on the rotary evaporator

  The solid body thus formed is analytically pure.

Melting point: mp = 176-177 ° C.

  Amount collected: 6.65 g, representing a yield of 83%.

  The compounds can be prepared in a similar manner

  forms to the invention which are cited in the following table.

  The letter d in the right column means "decomposition".

  Noj Name of the compound Constant substance hexy 11 oxy-2 (2-methyl-phenyl) -2- (1,2,4-triazol-1-yl) propiononitrile, hydronitrate butoxy-2 (2-methylphenyl) (triazole) 1,2,4-yl-1) -3-propiononitrile butoxy-2 (2-methyl-phenyl) -2- (1,2,4-triazole-1-yl) propiononitrile, hydronitrate hexyloxy2 (2-methyl-2-phenyl) -2 (triazole-1,2,4-yl) -3-propiononitrile-2-butoxy-2-phenyl-1,2-triazole-1-yl-1-propiononitrile, hydronitrate butoxy-2 (2-chlorophenyl) -2 (1,2,4-triazole-1-yl) -3-propiononitrile, 2-ethoxy-2-phenoxy-2-phenyl-1,2,4-triazol-1-yl) -propionitrile, 2-hydronitrate 2-phenyl-2-propoxy (triazole-1) , 2,4-yl-1) -3-propiononitrile, hydronitrate (3-chloro-phenyl) -2-hexyloxy-1,2,4-triazol-1-yl) propiononitrile, 2-butoxy-2-phenyl-2-phenyl-triazole 1,2,4-yl-1) -3-propiononitrile -2-phenyl-2-propoxy (1,2,4-triazole-1-yl) -3-propiononitrile 2-ethoxy-2-phenyl-1,2,4-triazole 1) -3 propionitrile

* F = 159-1620

(d) F = 58-620c

F = 158-161 ° C

(d) n D 0: 1.5121

Mp 159-1600 ° C

(D)

F = 142.5

-144 th C (d)

M.p. 169-170 ° C

(4)

Mp: 178-1790 ° C .;

(D)

Mp 173-1750 ° C

(D)

Mp 67680 ° C

M.p. 107-108 ° C

F = 74,750C

  No. Composition of the compound Physical Constituent 2-hexyloxy-2-phenyl-1-triazole-2,4-yl-1-propiononitrile, 2-allyloxy-2-phenyl-2 (triazole-1,2,4-yl) -3-propionitrile, Hydronitrate butoxy-2 (4-chlorophenyl) -2- (1,2,4-triazole-1-yl) propiononitrile, hydronitrate 2-allyloxy-2-phenyl-2-triazol-1,2,4-ylpropiononitrile 2-methoxyphenyl -2- (1,2,4-triazole-1H) -1-propiononitrile 2-hexyloxy-2-phenyl-1,2,4-triol-1-yl) propiononitrile (2-chlorophenyl) 2-hexyloxy-2-triazol-1,2,4-yl-1-propiononitrile, hydronitrate (2-chlorophenyl) -2-propoxy-2-thiazolin-1, 2,4-yl-1-propiononitrile, hydronitrate (chlorine) 4-phenyl) -2-propoxy-2- (1,2,4-triazol-1-yl) propiononitrile, hydronitrate (4-chlorophenyl) -2-hexyloxy-1,2,4-triazol-1-yl) -3 propionitrile, 2- (4-chlorophenyl) -2-propyloxy-2- (1,2,4-triazolyl) propiononitrile-2-butoxy- (4-chlorophenyl) (1,2-triazole) -2,4-triazole; 1) -3 propionitrile F = 158-1600 c <d)

F = 145-147 WC

(D)

M.p. = 173-175 ° C

(D)

F = 86 88 WC

F = 77 79 WC

Mp = 5860 ° C

F = 157-159 WC

CD)

F = 138-139 WC

(D)

F = 155-157 WC

(this)

F = 155-159 WC

(this)

F = 115-119 WC

F = 54 60 WC

  ################################################################################################################################################################################################################################################################################################################ 1,2,4-yl-1) -3-propiononitrile, 2-hydronitrate (2-methyl-phenyl) -2-octyloxy-2-triazol-1,2,4-yl-1-propiononitrile (2-chlorophenyl) butoxy 2- (1,2,4-triazole-11-yl) -3-propiononitrile (2-chloro-phenyl) -propoxy-2 (triazol-1,2,4-yl-1) -3-propiononitrile butoxy-2 (dichlorobenzene) 2,4-phenyl) -2- (1,2,4-triazole-1-yl) propiononitrile, hydronitrate butoxy-2 (2,4-dichlorophenyl) -2 (triazole-1,2,4-yl-1) -3 propiononitrile 2- (2,4-dichlorophenyl) -2- (3,4-triazole-1-yl) -3-propiononitrile 2- (3,4-dichlorophenyl) propoxy-2-triazole-1,2,4-yl-1-propionitrile 3-propiononitrile, hydronitrate (3,4-dichlorophenyl) -2-propoxy-1,2,4-triazole-1-propiononitrile

  (3,4-dichlorophenyl) -2-hexyloxy (triazole)

  1,2,4-yl) -3 propionitrile, hydronitrate

  3-phenyl-2-phenyl) hexyloxy-2 (triazole)

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

F = 128-134 WC

(D)

F = 116-120 WC

  (d) n D 2 1.4930 n D 0: 1.5273 n D 0: 1.5308

F = 163-1660 W

(D)

F = 53,550C

Mp 104-1070 ° C

Mp 152-155 ° C (d)

F = 60 66 WC

F = 166-168 WC

D = 1.5240

  No. Name of the compound Constant (4-fluoro-phenyl) -2-propyloxy-2 (1,3-triazole-1-yl) -propionitrile, 2-hydronitrate (2-fluoro-phenyl) -2-propoxy (1,2-triazole) , 4-VI-1) -3-propiononitrile butoxy-2 (4-fluoro-phenyl) -2- (1,2,4-triazole-1-yl) -3-propiononitrile, hydronitrate butoxy-2 (fluoro4 phenyl) -2 (triazole) 1,2,4-yl-1) -3-propionitrile (2-fluoro-phenyl) -propoxy-2 (1,2-triazole-1,3-yl-1-1-propiononitrile, 2-hydro-nitrate (2-fluorophenyl) propoxy) 2- (triazole-1, 2,4-yl-1) -3-propiononitrile-2-butoxy- (2-fluoro-phenyl) -2- (1,2,4-triazol-1-yl) propiononitrile, hydronitrate butoxy-2 ( 2-fluoro-phenyl) -2- (1,2-triazole-1-yl) -3-propiononitrile (2-fluoro-phenyl) -2-hexyloxy-1,2,4-triazole-1-propiononitrile, hydronitrate 2- (2-Fluoro-phenyl) -2-hexyloxy-1,2,4-triazol-1-yl) propiononitrile (4-bromo-phenyl) -propoxy-2 (1,2,4-triazole)

  3-propiononitrile, hydronitrate

  (2-bromo-phenyl) -2-propoxy-2-triazole-1,2,4-yl-1-propiononitrile,

Mp 172-1750 ° C .;

(d) F = 98-10 O to C

M.p. = 173-175 ° C

(D)

F = 56,500

Mp = 150-153 ° C (d) mp = 66-690 ° C

M.p.

(D)

F = 76790C

F = 134-137 o C (d)

F = 58,000

Mp 150-1530 ° C

(D)

M.p. 118-121 ° C

  Compound I name No phyiqu (2-methyl-phenyl) -2-hexyloxy-2 (1,2,4-triazol-1-yl) -3-propionitrile, hydronitrate (4-bromo-phenyl) 2-hexyloxy (triazole) 1,2,4-dl-1-propiononitrile (2,4-dichlorophenyl) -2-propoxy-2- (1,2,4-triazolyl) propiononitrile, 2,4-dichlorohydrate phenyl) -2-propoxy-2-triazo-1,2,4-yl-1-propiononitrile (2-methyl-phenyl) -2-pentyl-2-triazol-1,2,4-yl-1-propiononitrile, 2-hydronitrate (2-methyl-phenyl) -2-pentyl-1,2-triazole-1-yl) propiononitrile (4-methyl-phenyl) -2-propoxy (1,2,4-triazol-1-yl) 3-propionitrile, 2-hexyloxy-2-methyl-4-phenyl-2- (1,2,4-triazol-1-yl) -3-propiononitrile hydronitrate (4-methyl-phenyl) -2-propoxy-1,2-triazole; 4-yl-3-propiononitrile 2-hexyloxy-3- (4-methyl-phenyl) -2-triazol-1,2,4-yl-1-propiononitrile butoxy-2 (4-methylphenyl) (1,2-triazole) , 4 yl-1) -3 propiornonitrile

Mp: 161-1640 ° C .;

(D)

F = 60 6200

F = 166-170 ° C

(D)

Mp 61 630 ° C

Mp: 151-1540 ° C .;

(d) n 40 D

1.5111

Mp 170-1711 ° C

(D)

M.p. = 177-181 ° C

(d) F = 120-124 o C n D 40

1.5065

71 730 C

  3-arylsulfonyloxy and 3-alkylsulphonyloxypropiononitrile

  triles of general formula (II) (Y then denotes an arylsulfonyloxy or alkylsulfonyloxy radical) which serve as a body

  have never been described in the literature.

  They are obtained from phenylacetonitriles corresponding to the general formula (III):

O R 1

l

R CH IIII)

1

CN

  in which R and R 1 have the meanings that have been given

  above in relation to formula (I), compounds which are

  partly known or can be prepared by methods

  known from, for example, Rubin et al., JACS 67, 192 (1945); Hess et al., Ber et al. Chemes 50, 394, (1917) 1: these phenylacetonitriles are hydroxymethylated by known methods and the 3-hydroxypropiononitriles thus obtained, which correspond to the general formula (IV), are reacted:

O R 1

R C -CH 2 -OH (IV)

  CN with appropriate sulfonic acid derivatives, for example

  with sulphonic acid chlorides, possibly in the form of

  The presence of an acid acceptor The hydroxymethyl compounds of the general formula (IV) have not yet been described in

Literature.

  The preparation of a starting body is described below.

  Methylsulfonyloxy-3-phenyl-2-propoxypropionitrile

  27 g (0.154 mol) of 2-phenyl-2-propoxyacetate are dissolved in

  nitrile in 120 ml of pyridine and 18.5 g (0.614 mole) of paraformaldehyde is added to this suspension is added, while

  7.7 ml of tetrabutylhydroxide

  ammonium hydroxide (TBAOH) as a 40% solution and vigorously stirred After a few hours (thin layer chromatography test, "cce") the mixture is poured into ice water and extracted with water. The ether phase is washed with dilute hydrochloric acid and then with sodium chloride solution and dried over sodium sulfate.

  after filtering off the agent of

  cation and evaporating the solution on a rotary evaporator under reduced pressure a colorless oil is obtained which, according to the results of thin layer chromatography, consists of a single compound and which can be subjected to the subsequent reaction without complementary purification 28.4 g of 3-hydroxy-2-phenyl-2-propoxypropionitrile are collected, ie 90% of the theoretical amount. Its refractive index

n D is 1.5027.

  28 g (0.136 mol) of 3-hydroxy-2-phenylpropane are dissolved

  2-poxy propionitrile in 200 ml of toluene and 19.5 g (0.171 mol) of 10 C methanesulfonyl chloride are added

  18.6 g (0.184 mol) of triethylamine are added dropwise.

  After stirring for 30 minutes at room temperature, the precipitated triethylamine hydrochloride is removed by filtration and the residue is taken up with ether.

  washed with water, dried over magnesium sulphate and

  center According to the results of thin-layer chromatography, the oily residue is a pure compound. 32.27 g, ie 86% of the theoretical amount, of 3-methylsulphonyloxy-2-phenyl-2-propoxypropiononitrile, the of refraction

n D is 1.5000.

  The examples of execution described below illustrate

  the possibilities of applying the compounds according to the

  vention These are applied in the form of compositions

  such as those described above.

EXAMPLE 3

  Action of a prophylactic treatment of leaves against rust caused by Erysiphe graminis on barley, in the greenhouse On young barley plants having reached the stage of

  first sheet is applied by spraying until

  Drops with the indicated active substance concentrations drop off when the deposit thus applied by spraying is infected with dry spores of erysiphe treated plants as well as untreated control plants, by rubbing attacked plants on seedlings. studied After this, they are grown in a greenhouse at a temperature of approximately 20 to 22 ° C and, after one week, the degree of

  leaves The fungicidal action is given by the following

boasts: Fo F

A = 100

  F o in which: A represents the fungicidal action in% F represents the degree of attack of the untreated plant and

  F represents the degree of attack of the treated plant.

  The compounds are initially in the form of

compositions at 20%.

  N of the compound Action in% against Erysiphe graminis according to the invention 500 ppm 100 ppm

I 100 95

2,100 59

3 100 100

4 100 100

100 95

6,100 94

7,100 100

8 100 100

9 100 100

100 100

he 100 94

12 100 100

1 i 100 100

14 100 100

100 100

16 100 100

  N 'of the compound Action in% against Erysiphe graminis according to the invention 500 ppm 100 PPM O 1 00 3 3 4 4 1 52 1 00 9 5 1 00 O

EXAMPLE 4

  Action of a prophylactic treatment of leaves against Erysiphe cichoracearum on pumpkin plants in a greenhouse

  On pumpkin plants, sprays are applied

  until the droplets have reached the concentrations of active material indicated below and, when the deposit thus applied by spraying is dry, the plants are infected by sprinkling them with dry spores of Erysiphe cichoracearum, agent pathogen of the rust, then the plants treated, accompanied by untreated but infected control plants, are incubated in a greenhouse at 240 C. After one week, the surface attacked by the

  rust, in% relative to the total area of the leaves.

  The fungicidal action is calculated by the following relationship Fo -F

100

  F o where A represents the fungicidal action in%, F O represents the degree of attack of the untreated plant and

  F represents the degree of attack of the treated plant.

  The indication "s" in the following table means that the fungicidal action could also be observed on a rejection

  plants (after treatment) and was found positive.

  This means that the active ingredients are transported in the rejection and therefore have a systemic action: even on this one

  they have a 100% action against rust.

  The compounds are initially present in the form

of 20% compositions.

  N 'of the compound Action in% against Erysip'he cichoracearum according to the invention 250 ppm 1 25 ppm 5 ppm 2, PPMI 0.5 ppm

1 1 1

  z 1 5 2 O 1 4 t 1 9 1 O 1 1 1 2 1 3 1 4 1 6 1 7 1 9 2 1 2 2 3 9 SS ssss O sssssssss S ss s sss OO ssss 100 ssssssss -S ss S sss S s OOS - 99, 5 S

EXAMPLE 5

  Action (in%) of a Drophyllactic treatment of the leaves against Helminthosporium teres (= Pvrenophora teres), reticulated scab of barley On young barley plants having reached the stage of the first leaf, spray is applied to at

  dripping with drops, porridge with concentrates

  indicated in active matter.

  When the deposit thus applied by spraying is

  dry with a suspension of Helminthos conidiospores

  sporium teres treated plants and untreated control plants and incubated in a humid chamber for 2 days at 20-22 ° C. This is done, the plants are grown in a greenhouse at -22 ° C. One week after the innoculation, it is evaluated, in %, the degree of damage to the leaf surface The fungicidal action is calculated by the following relationship: Fo F

A = 100

  F o where: A represents the fungicidal action in%, F represents the degree of attack of the untreated plants and

  F represents the degree of attack of the treated plants.

  The compounds are initially in the form of

compositions at 20%.

  NO of the compound% action against Helminthosporium teres according to the invention 500 ppm 100 ppm 10 ppm - "

EXAMPLE 6

  Action of a prophylactic treatment of leaves against black rust Puccinia hordei on barley in an air-conditioned culture chamber On young barley plants having reached the stage of the first leaf is applied by spraying, until dripping drops, a slurry having the indicated concentration of active material When the deposit thus applied by spraying is dry infected treated plants and untreated control plants by rubbing with plants already suffering from rust, and put in a room The plants are cultivated at 15 ° C. for 10 days by operating, during the first two days, in air almost saturated with moisture. After this, the fraction of the surface of the leaves is determined in%. which is affected by rust The fungicidal action is calculated by the following relation:

F O F

A = 100

  Where A represents the fungicidal action in%, F O represents the degree of attack of the untreated plants and

  F represents the degree of attack of the treated plants.

  The compounds are initially present in the form

of 20% compositions.

  N O of the compound Action in% against Puccinia hordei according to the invention 500 ppm 100 ppm 20 PPM

EXAMPLE 7

  Action Against Pseudomonas Phaseolicola, Dathogen Agent for Bean Scab, In Vitro After sterilization with heat, a medium consisting of agar and biomalt is cooled to about 450 ° C and mixed with one of the compounds to be studied in the form of an aqueous composition, it is poured into a plastic petri dish After solidification of the nutrient medium

  infected by means of a seeding eyelet, in the

  The plates containing the treated agar as well as plates containing untreated agar, which are used as controls, with a suspension of the pathogen of the scab, Pseudomonas phaseolicola, are then incubated. The dishes are then incubated at 220 ° C. After 2 weeks and a half, the radial extension of the bacterial colonies which have developed from the average of two replicates per experimental section is measured. The bacterial inhibitory action is calculated by the following relationship: ## EQU1 ##

H = 100

  Where H denotes the inhibitory action in%, R is the radius of the growth zone in the untreated sample, and R is the radius of the growth zone in the treated sample. The compounds are presented initially. , Under the form

of 20% compositions.

  N of the compound in% Action with a concentration of 250 ppm active ingredient in the invention

12 62

73

21 64

24 66

EXAMPLE 8

  Action by the vapor phase against Helminthosporium teres on barley, in the greenhouse To study the activity by the vapor phase, a pot containing approximately 20 barley seedlings having reached the stage of the second fledgling leaf between two pots is placed. o are barley seedlings bearing a dried deposit from a treatment until dripping drops This treatment until dripping drops

  was carried out with a concentration of active ingredient of 0.1%.

  On the three pots, in each experimental section,

  throws a suspension of conidia from the pathogen of the

  reticulate scab, in this case Helminthosporium teres, suspended

  which was prepared with an aqueous solution of 0.05% sodium oleate and 0.02% gelatin and which was set at a spore concentration of 100,000 per milliliter. three pots, in each experimental section, in a polyethylene bag

  they are kept for 3 days at about 200 ° C. under conditions of

  Then, the bags are opened by cutting them at the height of the leaf tips. After 8 days, we count the cross-linked spots per pot. With the values thus obtained, we calculate the fungicidal action by the vapor phase using the following relation:

VO V

F = 100

V

  in which F represents the fungicidal action in%, VO the

  stains on unexposed barley and V number of tasks

on exposed barley.

  The compounds are initially present in the form

of 20% compositions.

  All steam exposures are well tolerated

by plants.

EXAMPLE 9

  Systemic action of pre-emergence soil treatment against oidium Erysiphe polyqoni in sugar beet, in the greenhouse After sowing sugar beet seeds in

  pots for plant cultivation these pots are sprayed

  with 0.3 kg of active ingredient per hectare and

  canned in the greenhouse at about 20 ° C next to untreated pots.

  After emergence of the beetroot (12 to 14 per pot), the plants are expected to produce the first two true leaves and then infected with dry spores of Erysiphe polygoni (oidium or true white). 3 weeks later (6 weeks after

  soil treatment) the degree of damage to the

  The fungicidal action could be manifested only by absorption of the compounds by the roots. It is calculated by the following relation Fo F

A = 100

  F o where A represents the fungicidal action in%, F the

  degree of attack of untreated plants and F the degree of

shade of treated plants.

  The compounds are initially present in the form N of the compound according to the invention.

2 1 00

3,100

4 99

100

13 85

  Comparison compound (4-chlorophenoxy) -1,3,3-dimethyl-1,2,4-triazole-1-butanone 86 of 20% compositions The treatments are all well tolerated by the plants and lead to more vigorous growth

* and tighter compared to the untreated control.

EXAMPLE 10

  Soybeans and wheat are sprayed

  by emulsions of the compounds to be studied.

  It is 2 kg of active ingredient per hectare. The plants are then grown in a greenhouse and after 3 weeks they are measured. The growth inhibitions that have been recorded,

  in%, are shown in the following table.

  N O of the compound according to the invention Action in%

12,100

13,100

14,100

  N 'of the compound Inhibition of the growth in% to the invention soy wheat

2 39 28

3 22 28

7 17 7

9 O 17

13 4 14

14 17 24

18 13 14

19 4 14

22 65 21

23 30 17

35 24

26 35 24

  Comparative compound: (2-chloroethyl) -trimethylammonium chloride O 17 It is found that the compounds according to the invention

  are, in general, more effective than the comparative compound

his.

EXAMPLE 11

  Pre-emergent rice is treated with the compounds

  forms of the invention at the dose of 2 kg of active ingredient per

  hectare After three weeks of greenhouse cultivation,

  undermines growth inhibition in e.

  The results are recorded in the following table.

  N 'of the compound according to the invention Inhibition of growth in% 22

7

26 14

Compound of comparison:

  (2-chloroethyl) -trimen-

  thylammonium O In the present application the comnaraison compound

  does not allow to achieve the inhibition of growth exerted

  the compounds according to the invention.

EXAMPLE 12

  Spray sugar beets are treated by

  pre-emergence, with a dose of 2 kg active ingredient per hectare.

  Inhibition of growth, in%, and staining of

  These are noted after three weeks of greenhouse cultivation.

  The results are recorded in the following table.

  No compound in accordance with Inhibition of Coloring the invention in% growth:

1 9 '1

3 34 1

7 34 O

8 37 O

9 25 1

37 O

12 22 O

13 41 O

14 41 O

16 53 O

17 53 O

18 22 1

19 37 O

37 1

21 6 1

22 37 1

23 53 2

24 22 1

69 2

26 37 2

Compound of comparison:

Chloride of (2-chloroethyl)

  trimethylammonium O O The coloring is noted as follows: 0 = identical to that of the control 1 = green more vivid 2 = dark green The compounds according to the invention act on the growth of the beet, a result that can not be achieved

  by the comparison compound in the present application.

EXAMPLE 13

  Prophylactic treatment of leaves against Fusarium culmorum, pathogen of scab, on panic (Pennisetum glaucum), in the greenhouse On young panic plants (approximately 30 per pot) having reached the stage of the second fledgling leaf sprays of the indicated concentrations are applied by spraying until the droplets have driped off. When the deposit thus applied by spraying is dry, the treated plants and untreated control plants are sprinkled with a suspension of conidia of Fusarium culmorum. and we keep them

  in a humid state, in a greenhouse, at a temperature of about 22 C.

  After 4 days, the fraction of leaf area that is reached is evaluated in%. The fungicidal action is calculated by the following relationship: Fo F

A = 100

  F o where A represents the fungicidal action in%, Fo the degree of attack of the untreated plants and F that of the treated plants. The compounds are initially in the form of

compositions at 20%.

EXEMPLE'14

  Prophylactic treatment of leaves against Cercospora beticola, pathogen of leaf scab, on sugar beet, in the greenhouse On sugar beet plants with at least

  two well-developed true leaves are sprayed

  After the deposition thus applied by spraying, the treated plants, together with untreated control plants, are sprayed with a suspension of conidia of Cercospora beticola and incubated. in the humid state in the greenhouse at 26 ° C. for 2 days After that, the plants are grown under normal greenhouse conditions. Two weeks' action in% with N of the compound according to the invention Acion in% with 500 ppm 100 ppm

2,100 100

3 91

9 80

12 90

13,100

14,100

16 95

17 95

18 95

1990

80

22 99 90

23 100 99

24 100 97

100 98

26 98 93

27 90

29 97 90

97 90

31 100 98

  after treatment, the degree of impairment in% is evaluated.

  The fungicidal action is calculated by the following relation: Fo F

A = 100

  F o where A represents the fungicidal action in%, F the o degree of attack of untreated plants and F that of

treated plants.

  The compounds are initially present in the form

of 20% compositions.

  N of the compound according to the invention Action in% with 500 ppm 100 ppm

3 100 100

he 93

12 93

13,100

14 93

16,100

17 87

19 93

87

21 100 96

22 100 100

23 100 100

24 100 100

96 96

26 100 96

27 98 98

28 100 98

29 100 98

100 100

31 100 100

EXAMPLE 15

  Seed-borne Helminthosporium sativum Seed Disinfection Treatment on Barley Barley Seed Infected with Helminthosporium sativum at a 50 mg dose of active ingredient per 100 g 2 g of seed are sown in pots, in two replicates, taken, on the one hand, on that which has been treated and, on the other hand, on another which has not been treated

  and incubated at 15 ° C in an air-conditioned chamber.

  Before the emergence of the plants they are exposed to an artificial light with an alternation of 12 hours After 4 weeks the percentage of plants with foot disease is determined.

treated does not escape the disease.

  N of the compound according to the invention Action in%

2,100

3 99.5

4,100

99.5

  The compounds are initially present in the form

of 20% compositions.

EXAMPLE 16

  Action of a seed treatment against Phoma betae vehi-

  seeded on sugar beet Phoma betae infected sugar beet seed treated with 250 mg of active ingredient for 25 seeds each Seeded in 25-seeded pots each time taken from the seed that has been treated as well as that which has not received any treatment, and they are kept at 150 C in an air-conditioned room. When the plants have been raised, they are exposed to artificial lighting with an alternation of 12 hours. Until the end of the experiment, which lasts 7 weeks, we count the plants that have fallen sick each week and we remove them. Among the control (untreated) plants that have emerged we find a total proportion of patients of 76.1%.

  protection of the treatment is calculated by the following

boasts: Fo F

P = 100

  F o where P represents the protective action in%, F the o degree of attack of untreated plants and F that of

treated plants.

  The compounds are initially present in the form

of 20% compositions.

  N of the compound according to the invention Action in%

2,100

3 97

four hundred ninety seven

100

6 83

12 92

13 99

14 96

Compound of comparison:

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

  (1,1-Dimethylethyl) -1H-1,2,4-triazol-1-ethanol 51 (4-chlorophenoxy) -1,3-dimethyl-3,3-triazole-1,2,4-yl-1-yl butanone-2 57

Claims (7)

  1 (1,2,4-Triazolyl) -propionitrile having the general formula (I): O -R 1 N. R C CH 2 N () N in which:   R represents an aromatic hydrocarbon radical which may be   carrying one or more substitute   identical or different radicals selected from the group consisting of halogens, C 1 -C 4 alkyls, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, trifluoromethyl radical and nitro radical; and R 1 represents C 1 -C 10 alkyl, C 3 -C 8 alkenyl,   C 3 -C 8 alkynyl or a phenylalkyl radical,   with one or more substituents   substituents, identical or different, taken in   It consists of halogens, C 1 -C 4 alkyls, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, trifluoromethyl radical and nitro radical, as well as the addition salts which they form with acids minerals or organic.   2 (Triazole-1,2,4-yl-1) -propionitrile according to claim 1, wherein: R represents a phenyl radical optionally carrying   of a substituent or substituents, identi-   different from the group consisting of halogens, C 1 -C 4 alkyls,   C 1 -C 4, C 1 -C 4 alkylthio, trifluoromethyl   thyl and the nitro radical, and R 1 represents a C 1 -C 10 alkyl, a C 3 -C 8 alkenyl, or a benzyl optionally carrying one or more substituents, identical or different, taken as a whole consisting of halogens, C 1 -C 4 alkyls, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, C 1 -C 4 alkylthio, C 1 -C 4 alkylthio, and the like. 3 (Triazole-1,2,4-yl) -propionitrile taken from the group consisting of 2-isopropoxy-2-phenyl-1,2,4-triazole-1-propionitrile, hydronitrate   2-isopropoxy-2-phenyl-1,2,4-triazole (1-yl) propiononi   trile, 2-hexyloxy-2- (2-methylphenyl) -2- (3-triazol-1, 4-yl) propiononitrile, hydronitrate, butoxy-2 (2-methylphenyl) -2 (triazole) 1,2 , 4-yl-1) -3-propionitrile, butoxy-2 (2-methylphenyl) -2 (triazole1,2,4-yl-1) -3-propiononitrile, hydronitrate, hexyloxy-2 (2-methylphenyl) - 2 (triazole-1,2,4-yl-1) -3-propionitrile,   2-butoxy-2-phenyl-1,2,4-triazole-1-ylpropiononitrile   trile, hydronitrate, butoxy-2 (2-chloro-phenyl) -2 (triazol-1,2,4-yl-1) -3-propiononitrile, hydronitrate,   2-ethoxy-2-phenyl-2-triazol-1,2,4-ylpropiononi trile, hydronitrate,   2-phenyl-2-propoxy (1,2,4-triazol-1-yl) propionic acid   trile, hydronitrate, 2- (3-chlorophenyl) -2-hexyloxy (1,2,4-triazolyl) propiononitrile, hydronitrate,   2-butoxy-2-phenyl-1,2,4-triazol-1-ylpropionitrile Trile,   2-phenyl-2-propoxy-1,2,4-triazol-1-ylpropionitrile   trile, 2-ethoxy-2-phenyl-1,2,4-triazol-1-ylpropiononitrile,   2'-hexyloxy-2-phenyl-2 (1,2,4-triazole-1-yl) propiononi trile, hydronitrate,   2-allyloxy-2-phenyl-1,2,4-triazole-1-ylpropionic acid trile, hydronitrate,   2-butoxy-4-chlorophenyl) -2-triazole-1,2,4-yl-3-yl piononitrile, hydronitrate,   2-allyloxy-2-phenyl-1,2,4-triazol-1-ylpropiononi Trile,   2-methoxy-2-phenyl-2-triazol-1,2,4-ylpropiononi Trile,   2-hexyloxy-2-phenyl-2-triazine-1,2,4-yl-1-propiononi   trile, 2-chloro-2-phenyl-2-hexyloxy-1,2,4-triazole-1-propiononitrile, hydronitrate, 2- (2-chlorophenyl) -2-propoxy triazole , 4-yl-1-propiononitrile, hydronitrate, 2- (4-chlorophenyl) -2-propoxy (1,2,4-triazole-1-yl) propiononitrile, hydrochloride, (4-chlorohydrate) phenyl) -2-hexyloxy-2- (1,2,4-triazole-1-yl) propiononitrile, hydronitrate, 2- (4-chlorophenyl) -2-propyloxy (1,2,4-triazole-1-yl) Propionitrile, butoxy-2 (4-chlorophenyl) -2- (1,2,4-triazole-1-yl) -3-propiononitrile, 2- (2-methylphenyl) -2-octyloxy-1,2-triazole, 4 yl-1) 3 propionitrile, hydronitrate, 2-decyloxy-2- (2-methylphenyl) -2- (1,2,4-triazole-1-yl) propiononitrile, hydronitrate, 2- (2-methylphenyl) octyloxy -2- (1,2,4-triazole-1-yl) -propionitrile, 2- (2-chloro-phenyl) butoxy-2- (1,2,4-triazol-1-yl) propiononitrile, (chloro2-ph-6-yl) 2-propoxy-2-triazol-1,2,4-yl-3-propiononitrile, butoxy-2 (2,4-dichlorophenyl) -2 (1,2,4-triazole-1-yl) -3 propiononitril e, hydronitrate, butoxy-2 (2,4-dichlorophenyl) -2- (1,2,4-triazole-1-yl) -propiononitrile, -2-allyloxy-2,4-dichlorophenyl) (1,2,4-triazolyl) propionitrile, 3,4-dichlorophenyl-2-propoxy-2- (1,2-triazole-1-yl) propiononitrile, hydronitrate, 3,4-dichlorophenyl) -2-propoxy-2- (1,2,4-triazol-1-yl) -propionitrile, 3,4-dichlorophenyl-2-hexyloxy-1,2,4-triazole 3- (3,4-dichlorophenyl) -2-hexyloxy (1,2,4-triazole-1-yl) propiononitrile, 2- (4-fluorophenyl) propoxonitrile, propionitrile, hydronitrate, 2 (triazole-1,2,4-yl) propiononitrile, hydronitrate, 4-fluorophenyl) -2-propoxy-1,2,4-triazol-1-propiononitrile, butoxy 2- (4-fluoro-phenyl) -2-triazole-1,2,4-triol-1,2-propiononitrile, hydronitrate, butoxy-2 (4-fluoro-phenyl) -2 (1,2,4-triazole) yl -1) -3-propionitrile, 2- (2-fluoro-phenyl) propoxy-2 (1,2,4-triazole-1-yl) propiononitrile, hydronitrate, 2-fluorophenyl-2-protpoxy-2 ( triazole-1,2,4 yl-1) -3 pro piononitrile, 2-butoxy-2-fluoro-phenyl-2 (1,2,4-triazol-1-yl) propiononitrile, hydronitrate, 2-butoxy-2-fluoro-phenyl) (1,2-triazole, 4-yl-3-propionitrile, 2-fluoro-phenyl-2-hexyloxy-2-triazole-1,2,4-ylpropiononitrile, hydronitrate, 2-fluoro-phenyl-2-hexyloxy (1,2,4-triazole-1-yl) -3-propionitrile, 2- (2-bromophenyl) -2-propoxy (1,2,4-triazol-1-yl) propylonitrile, hydronitrate, bromo 3- (2-propyl-2-triazol-2-propyl) -1-propiononitrile, 2- (2-bromo-phenyl) -2-hexyloxy-1,2,4-triazol-1-yl) - 3-propiononitrile, hydronitrate, 2- (2-bromo-phenyl) -2-hexyloxy (1,2,4-triazole-1-yl) propiornonitrile, 2- (2,4-dichlorophenyl) propoxy-2 (triazole) 1,2,4-yl-1) -3-propiononitrile, hydronitrate, 2- (2,4-dichlorophenyl) -propoxy-2-propoxonitrile (2-methyl-1,2,4-triazole) phenyl) -2-pentyl-2-triazole-1,2,4-yl-1-propiononitrile, hydronitrate, 2-methyl-2-phenyl-2-pentyl-1,2,4-triazole-1-yl) 3 p 2-propoxonitrile, 2- (4-methyl-phenyl) -2-propoxy-1,2-triazole-2-propiononitrile, hydronitrate, hexyloxy-2 (4-methyl-phenyl) -2- (triazole) 1,2,4-yl-1) -3-propionitrile, hydronitrate, 2- (4-methyl-phenyl) -2-propoxy (1,2,4-triazol-1-yl) propiononitrile, 2-hexyloxy (methyl) 4-phenyl) -2- (1,2,4-triazole-1-yl) propionitrile and 2-butoxy-4- (4-methyl-phenyl) -triazole-1,2,4-yl-1-propiononitrile.   4 Process for the preparation of (1,2,4-triazole-1-yl)   propionitrile according to any of claims 1   at 3, characterized in that compounds of   wherein R 1 and R 2 have the meanings given in claim 1 and Y is halogen or arylsulphonyloxy or alkylsulphonyloxy optionally halogenated in the side chain, together with the triazole-1. 1,2,4, which compound has the following formula: N CH He 11 HC N   HN or one of its alkali metal derivatives, in the presence of a   solvent and optionally in the presence of a base.   Biocidal products are characterized   hold at least one compound according to any one of the 1 to 3.   Biocidal products according to claim 5 which have a fungicidal action.   Biocidal products according to claim 5 which   have a regulatory action on growth.   Biocidal products according to claim 5 which have a bactericidal action.   Biocidal products according to claim 5 which   also contain carriers and / or adjuvants.