JPS6055070B2 - Imidazolyl-propionitrile, its production method, and fungicides containing the compound - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a new imidazolyl-probionitrile, a process for its production and a fungicide containing this compound, in particular having fungicidal action.

Imidazolyl-probionitrile derivatives having fungicidal action are already known (West German Patent Application No. 2)
No. 604047).

However, this compound has a relatively narrow spectrum of action, which is unsatisfactory. The object of the present invention is to develop new imidazolyl-probionitriles which have a broadly differentiated use and have a broad spectrum of fungicidal action, especially for the field of plant protection.

According to the present invention, this problem can be solved by the general formula 1: [wherein R is a halogen atom, (C1-C4)-alkyl group, (C
, ~C4)-alkoxy group, (C1-C4)-alkylthio group, trifluoromethyl group or nitro group 1
represents the same or different aromatic hydrocarbon groups which may be substituted one or more times, and R1 is (C1 to ClO
)-alkyl group, (C, ~C8)-alkenyl group, (C
3-C8)-alkynyl group, or halogen atom, (C1-C4)-alkyl group, (C1-C4)-alkoxy group, (C1-C4)-alkylICthio group, trifluoromethyl group or nitro group represents the same or different phenylalkyl group which may be substituted one or more times by imidazolyl-probionitrile and its acid addition salts with inorganic and organic acids. It will be decided.

It is surprising that the compounds according to the invention exhibit a bactericidal action within the widest range, but are particularly pronounced in their fungicidal action, in which they surpass the known active substances of the same structure and direction of action. There are two things.

This fungicidal action is surprisingly effective against fungi of a wide variety of phylogenetic positions.

This action protects against wind-borne pathogens when processing plant parts on the soil surface. The compounds can be used to treat seed against pathogens that can be carried in the seed. Furthermore, this compound has systemic properties, ie it is absorbed by the roots of the plant, for example in the seeds after planting, and is transported to the soil surface part of the plant, and this soil surface part! protects against pathogens. Other actions include growth regulating action and bactericidal action.

Due to the broad spectrum of action detected, this compound can be used not only for the protection of cultivated plants. They are also suitable for the protection of substances and for the control of human-pathogenic and veterinary microorganisms, which gives rise to a wide variety of uses.

Depending on the detailed meaning of the substituents, important fields of use are obtained here, in which the compounds exhibit outstanding effects. The compounds can therefore be used in each case as fungicides, plant growth regulators or fungicides. In the case of compounds represented by general formula 1, two examples can be given: 2-fluorophenyl group, 3-fluorophenyl group, 4-fluorophenyl group, 2-chlorophenyl group. , 3-chlorophenyl group, 4-chlorophenyl group, 2-bromphenyl group, 3-bromphenyl group, 4-bromphenyl group, 2-iodophenyl group, 3-
Iodophenyl group, 4-iodophenyl group, 2,3-dichlorophenyl group, 2,4-dichlorophenyl group, 3,
4-dichlorophenyl group, 2,6-dichlorophenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-
Methylphenyl group, 2-ethylphenyl group, 3-ethylphenyl group, 4-ethylphenyl group, 2-propylphenyl group, 3-propylphenyl group, 4-propylphenyl group, 2-isopropylphenyl group, 3-isopropylphenyl group group, 4-isopropylphenyl group, 2-butylphenyl group, 3-butylphenyl group, 4-butylphenyl group, 2-Sec-butylphenyl group, 3-Sec-butylphenyl group, 4-Sec-butylphenyl group, 2-
Tert-butylphenyl group, 3-Tert-butylphenyl group, 4-Tert-butylphenyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 2-ethoxyphenyl group, 3-ethoxyphenyl group group, 4-ethoxyphenyl group, 2-methylthiophenyl group, 3-methylthiophenyl group, 4-methylthiophenyl group, 2-ethylthiophenyl group, 3-ethylthiophenyl group, 4-ethylthiophenyl group, 2-trifluoro 3-trifluoromethylphenyl group, 4-trifluoromethylphenyl group, 2-nitrophenyl group, 3-nitrophenyl group, 4-nitrophenyl group, 3-fluoro-4-methoxyphenyl group, 2
-chloro-5-nitrophenyl group, 4-chloro-2-fluorophenyl group, 3,4,5-trimethoxyphenyl group, or 5-chloro-2-nitrophenyl group and R1
(C1-ClO)-alkyl group, such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, isopropyl group, 2,2-dimethyl-propyl group Roux 1, 3,
3-dimethyl-butyl-2 group, (C3-C8)-alkenyl group, such as 2-buten-1-yl group, 3-methyl-2-buten-1-yl group, hexenyl group, heptenyl group, octenyl group, (C3-C8 )-alkynyl groups, such as propargyl, butynyl, pentynyl, hexynyl, heptynyl, octynyl, phenylalkyl groups, such as benzyl, 2-fluorobenzyl, 3
-Fluorobenzyl group, 4-fluorobenzyl group, 2
-Chlorobenzyl group, 3-chlorobenzyl group, 4-chlorobenzyl group, 2-bromobenzyl group, 3-bromobenzyl group, 4-bromobenzyl group, 2,4-dichlorobenzyl group, 2,6-dichloro Benzyl group, 3,4-dichlorobenzyl group, 2-methylbenzyl group, 3-methylbenzyl group, 4-methylbenzyl group, 2-nitrobenzyl group, 3-nitrobenzyl group, 4-nitrobenzyl group, 2-
Trifluoromethylbenzyl group, 3-trifluoromethylbenzyl group, 4-trifluoromethylbenzyl group, 2
-methoxybenzyl group, 3-methoxybenzyl group, 4-
Methoxybenzyl group, 2-ethoxybenzyl group, 3-ethoxybenzyl group, 4-ethoxybenzyl group, 2-propoxybenzyl group, 3-propoxybenzyl group, 4-propoxybenzyl group, 2-butoxybenzyl group, 3-butoxybenzyl group group, 4-butoxybenzyl group, 2-methylthiobenzyl group, 3-methylthiobenzyl group, 4-methylthiobenzyl group, 2-ethylthiobenzyl group, 3,
-ethylthiobenzyl group, 4-ethylthiobenzyl group,
Examples include 2-butylthiobenzyl group, 3-butylthiobenzyl group, and 4-butylthiobenzyl group.

Inorganic and organic acids which form acid addition salts include, for example, hydrohalic acids, such as hydrochloric acid and hydrobromic acid, phosphoric acid, sulfuric acid, especially nitric acid, monofunctional and difunctional carboxylic acids, Acids and hydroxycarboxylic acids such as acetic acid,
maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid,
Mention may be made of salicylic acid, -sorpic acid, lactic acid, and sulfonic acids, such as p-toluolsulfonic acid and 1,5-naphthalene disulfonic acid.

The acid addition salts can be obtained by conventional salt formation methods, for example by dissolving the compound of formula 1 in a suitable solvent and adding an acid.

Compounds according to the invention, in particular in the general formula 1, in which the radical R is a nitrogen atom, a (C1-C4)-alkyl group, a (C1-C4)
- represents an identical or different phenyl group, optionally substituted one or more times by an alkoxy group, a (C1-C4)-alkylthio group, a trifluoromethyl group or a nitro group, and the radical R1 ~C6)-Alkyl group, allyl group, propargyl group, or halogen atom, (C1-C4)-alkyl group, (C1-C4)-
Those representing the same or different benzyl groups, which may be substituted one or more times by alkoxy, (C1-C4)-alkylthio, trifluoromethyl or nitro groups, are significant for their fungicidal action. It is.

This preferably includes R being a phenyl group, a 2-chlorophenyl group, a 3-chlorophenyl group, a 4-chlorophenyl group, a 2-chlorophenyl group,
, 4-dichlorophenyl group, 2,6-dichlorophenyl group, 3,4-dichlorophenyl group, 2-fluorophenyl group, 4-fluorophenyl group, 4-bromphenyl group, 2-methylphenyl group group, 4-methylphenyl group, 4-
Represents a methoxyphenyl group, 4-nitrophenyl group,
and R1 is a methyl group, ethyl group, propyl group, isopropyl group, pentyl group, hexyl group, allyl group, propargyl group, benzyl group, 2-chlorobenzyl group, 4-chlorobenzyl group, 2,4-dichlorobenzyl group 3,4-dichlorobenzyl group.

The following compounds according to the invention exhibit an outstanding effect: 2-
n-Butoxy 2-(2-chlorophenyl)-3-(imidazol-1-yl)-probionitrile, hydrogen nitrate, 2-n-butoxy 2-(2-chlorophenyl)-
3-(imidazol-1-yl)-probionitrile,
2-n-Butoxy(4-chlorophenyl)-3-(imidazol-1-yl)-probionitrile, hydrogen nitrate, 2-(4-chlorophenyl)-3-(imidazol-1-yl)- 2-n-propoxypropionitrile,
Hydrogen nitrate, 2-(2-chlorophenyl)-3-(imidazol-1-yl)-2-n-propoxypropionitrile.

The compounds according to the invention exhibit a particularly fungicidal action, but at the same time are notable for their growth-regulating action in a range of cultivated plants.

As already mentioned, the compounds according to the invention are transported systemically into plants.

Accordingly, this compound exerts its growth-regulating effect when applied onto the soil as well as during spray treatments.

The growth-inhibiting effect is particularly pronounced in the case of sagebrush and cotton.

In addition to the actions mentioned above, the compounds according to the invention also exhibit a bactericidal action, making them acceptable for other uses.

The compounds according to the invention can be used alone or in admixture with one another or with other active substances. Optionally, further plant protection agents or pesticides can be added depending on the desired purpose. The active substances or mixtures thereof may be present in preparations, for example in the form of powders, dusting powders, granules, solutions, emulsions or suspensions, with liquid carriers and/or solid carriers or diluents and in some cases. It may be advantageous to use wetting agents, adhesives, emulsifiers and/or dispersing agents.

Suitable liquid carriers are, for example, water, aliphatic and aromatic hydrocarbons, such as penzole, toluol, xylol, cyclohexanone, isophorone, dimethylsulfoxide, dimethylformamide, and also mineral oil fractions and vegetable oils.

Solid carriers include minerals such as clay, silica gel,
Talc, kaolin, attapulgiaite, coalstone, silicic acid and vegetable products such as flour are suitable.

Regarding surfactants, the following may be mentioned: for example calcium ligninsulfonate, polyoxyethylene alkyl phenyl ethers, naphthalenesulfonic acid and its salts, phenolsulfonic acid and its salts, formaldehyde condensates, fatty alcohol sulfuric acid. Salts and substituted benzenesulfonic acids and their salts.

If the active substances have to be used for soaking seeds, dyes can also be incorporated in order to give the soaked seeds a clearly visible color.

The content of active substance in the various modifiers can vary within wide limits.

For example, the medicament contains about 10 to 9% by weight of active substance, about 90 to 90% by weight of a liquid or solid carrier, and optionally up to 2% by weight of surfactant. The drug is dispersed in a conventional manner, for example, with water as a carrier at a concentration of about 100 to 10
This can be done with a spray throughput of 00'/Ha.

The drug is applied using the so-called “low-volume spraying method” (LOw-VOlume-Ve).
rfahren) 1' or 66 microspray method (Ultra
Upper 0w-VOlurne-Verfa-Hren)55
It is just as possible to apply the powder in the form of so-called fine granules. To produce the preparation,
For example, the following ingredients are used: A. Spray pitch a) Active substance clay silicic acid cell pitch αEllpech) Surfactant based on a mixture of calcium salts of lignosulfonic acid and alkylphenol polyglycol ethers b) Active substance kaolin silicate N-methyl-N-ole Surfactants based on the sodium salt of yl-taurine and the calcium salt of lignosulfonic acid c) Active substances clay silicic acid cell pitch 1e1.1qech) Surfactants based on calcium salts 40wt1% 25wt% 20wt% 10wt% 5wt% 25wt% 60wt% 10wt% 5wt% 10wt% 60wt% 15wt% 10wt% 5 Weight I% B Paste active substance 45% by weight Sodium aluminum silicate 5% by weight Cetyl polyglycol ether with 8 moles of ethylene oxide 15% by weight Spindle oil 2% by weight Polyethylene glycol 1 Weight % Water 2? C Concentrated emulsion active substance 25% by weight cyclohexane 15% by weight xylol
55% by weight mixture of nonylphenyl polyoxyethylene and calcium dodecyl penzole sulfonate.

The novel compounds according to the invention can be prepared, for example, by the general formula (1): [wherein R and R1 are as defined above and Y represents a halogen atom or alkylsulfonyloxy or aryl which may be halogenated in the side chain] [representing a sulfonyloxy group] can be produced by reacting a probionitrile represented by the formula: with an imidazole represented by the formula: in the presence of a solvent and optionally in the presence of a base.

Examples of the nitrogen atom include a chlorine atom, a bromine atom, or an iodine atom; suitable examples of the alkylsulfonyloxy group include a methyl group, an ethyl group, a propyl group, and a trifluoromethylsulfonyloxy group; Examples of the sulfonyloxy group include a benzylsulfonyloxy group and a p-toluolsulfonyloxy group.

The reaction can be carried out with an excess of imidazole, optionally in the presence of a solvent, or with the addition of a strong base, for example sodium hydroxide or monopotassium.

Furthermore, imidazole-alkali metal may be used in place of imidazole. As solvents, substances which are inert towards the reactants and preferably have polar and neutral properties, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, tetramethylurea,
Hexamethylphosphoric acid triamide and benzonitolyl are suitable, but also high-boiling aromatic and aliphatic hydrocarbons, such as toluene, tribenzol or xylol.

Reaction temperatures can vary within wide ranges.

Advantageously, the temperature is between 100C and 20CfC. The reaction is carried out under normal pressure or overpressure. The imidazolyl-probionitriles according to the invention are generally almost colorless and odorless oils.

The acid addition salts derived therefrom are colorless and odorless crystalline compounds. This oil is not very soluble in water, but
It is more or less well soluble in organic solvents such as alcohols, ethers or chlorinated hydrocarbons. Acid addition salts are partially soluble in water and well soluble in polar organic solvents such as acetonitrile, N,N-dimethylformamide, lower alcohols, chloroform and methylene chloride. The following examples detail the preparation of compounds according to the invention. Example 1 3-(imidazol-1-yl)-2-phenyl-2-
Propoxypropionitrile, hydrogen nitrate (compound N
O. l) 3-methylsulfonyloxy-2-phenyl-2-propoxypropionitrile 15g (a). 053 mol) and imidazole 17.8 g (4). 263 mol) with the addition of 1 ml of dimethylformamide and with exclusion of water.
It was held at 0°C for 1 hour.

This solution was poured onto ice water and added twice with 75 ml of methylene chloride.
The methylene chloride phase is washed twice with water, dried over magnesium sulfate and, after separation, concentrated in vacuo with a drying agent.

The remaining dark oil is dissolved in isopropanol and slightly more than the theoretical amount of 100% nitric acid is added to this solution. Some diethyl ether is added to complete the precipitation. The precipitated product is filtered off with suction and dried. yield:
12g = 71% of theory Melting point: 168-171°C (decomposition) Example 2 3-(Imidazol-1-yl)-2-phenyl-2-
Propoxypropionitrile (compound NO2) Hydrogen nitrate of Example 1 6.2 g (4). 0195 mol) in methanol and the solution is made basic with dilute ammonia solution under ice bath cooling.

After diluting the solution with water, it is extracted with ethyl acetate, the organic phase is washed with water and then dried over magnesium sulphate. The solution is filtered through P and concentrated in vacuo. An oil remains and is dried in vacuo. Yield: 4.85
g=97% of theory NW=1.5260 The following compounds according to the invention can be prepared in a similar manner.

Compound name Physical constant 3.2-poxy 3-(imidazo Melting point: -1-
yl)-2-phenylene 155-157°C, propionitrile, nitric acid water (decomposition) base salt 4.2-phenyl 3-
(Imidazo ND39:-1-yl)-2-7eni
1.5208-propionitrile 5.2-allyloxy-3-(imi melting point: dazol-1-yl)-2-phenyl-probionitrile,
(Decomposition) Hydrogen nitrate 6.2-allyloxy-3-(imiND33: Dakaryl-1-yl)-2-ph 1.5402
enyl-probionitrile 7.2-ethoxy3-(imidazo melting point:-1-yl)-2-pheny182-
186℃L-propionitrile, nitric acid water (decomposition) Basic salt 8.2-Ethoxy 3-(imidazo ND44:-1
-yl)-2-phenyl 1.5247-propionitrile Compound name Physical number 9.3-(imidazol-1-yl) Melting point: -2-methoxy-2-phenyl 189-191°C - Probionitrile, hydrogen nitrate Salt (decomposition) 10.3-(imidazol-1-yl) Melting point: -2-methoxy-2-phenyl 57
-60℃ -probionitrile 11.2-(2-chlor 7
(enyl)1 Melting point: 3-(imidazo-1-yl)1
62-165℃ - 2-Propoxypropioni (decomposition) Tolyl, hydrogen nitrate 12.2-Butoxy 2-(4
-Chloro Melting point: Rufenyl)-3-(Imidazo178-
181℃ → Le-1-yl)-propioni (Decomposition) Tolyl, Hydrogen nitrate 13.2-Butoxy 2-(2-chloro Melting point: Ruphenyl)-3-(Imidazo 177-178℃ 1-R-1-yl)
-Propionitrile (decomposition) Tolyl, hydrogen nitrate 14.2-Allyloxy-2-(2-melting point: clophenyl)-3-(imidazol-1-yl)probionitrile, hydrogen nitrate 15.2-(4-chloro) 7-enyl)-3-(imidazo-1-yl)-2-propoxypropionitrile, hydrogen nitrate 716.2-allyloxy-2-(4-chloro7enyl)-3-(imidazo-1-yl) -probionitrile, hydrogen nitrate 717.2-(2-chlorophenyl)-13-(imidazo→ray-1-yl)-2-proboxypropionitrile 18.2-putquine-2-(4-chlorphenyl) 153-155℃ (decomposition) Melting point: 174-177℃ (decomposition) Melting point: 152-15 (decomposition) ) (Decomposition) 41● ND・ 1.5343 41・ ND・ 1.5288 41・ ND・ Compound name lor7enyl)-3-(imidazol-1-yl)-probionitrile 20.2-allyloxy-2- (2-Chlorphenyl)-imidazol-1-yl)-probionitrile 21.2-(4-chlorphenyl)-3-(imidazol-1-yl)-2-propoxypropionitrile 22.2-allyloxy-2-( 4-Chlorphenyl)-3-imidazol-1-yl)-probionitrile 23.2-benzyloxy-3- (imidazol-1-yl) 12-7enyl-probionitrile, hydrogen nitrate 24.2-benzyloxy-3-(imidazol-1-yl) 3-(Imidazol-1-yl) -2●7enyl-probionitrile 25.3-(Imidazol-1-yl)-2-isopropyloxy-2-phenylpropionitrile, hydrogen nitrate 26.3- (Imidazol-1-yl)-2-isopropyloxy-2-7enyl-probionitrile 27.2-(4-chlor7-l)-12-hexyloxy-3-(imidazo-1-yl) -Probio Nitrile, hydrogen nitrate 28.2-(4-chlor7enyl) 12-hexyloxy-3-(imidazol-1-yl) -probionitrile physical constant 1.5329 41. ND. 1.5490 41. ND. 1.5337 41・ND・1.5476 Melting point: 166-168℃ (decomposition) 40・ND・1.5638 Melting point: 165-16℃ (decomposition) 40・ND・1.5254 Melting point: 152-154℃ (decomposition) ) 40・ND・1.5197 Compound name Physical constants 29.2-allyloxy-3-(a) Melting point: midazol-1-yl-2160℃-(2-methylphenynoly (decomposition)) Probionitrile, nitrohydrogen salt 30.2-(3,4-dichlorophenyl) Melting point: -3
-(Imidazole 1- 169-170℃ Inolly 2
-Propoxyp (Decomposition) Bionitrile, Nitrate hydrogen salt 31.2-Butoxy 2-(2,4 melting point: -dichlorophenyl) -3- 148-150℃ (imidazo-
(decomposition) - Probionitrile, hydrogen nitrate 32.2-allyloxy-2-(2, melting point: 4-dichloro7enyl) -3158-160℃ -(imidazo-1-yl) (decomposition) - Probionitrile, hydrogen nitrate 33.2-Ethoxy 2-(3,4 melting point: -dichlorophenyl) -3- 105-106°C (Imidazole 1
-yl) (decomposition) -probionitrile, hydrogen nitrate 34.2-allyloxy-3-(iN.

4O: midazol-1-yl)-21.5388-(2
-Methylphenyl)-Probionitrile 35.2-(3,4-dichlor7-N-D4O:Nil)
-3-(imidazole 1.5360-1-yl)-
2-Propoxypropionitrile 36.2-allyloxy-2-(3,nD40:4-dichlor7enyl)-31.5500-(imidazo-1-yl)-probionitrile37.2-poxy-2-(2 ,4-ND40:dichlorophenyl)-3- 15381(imidazo→ray-1-yl)-probionitrile Compound name Physical constant 38.2-allyloxy-2-(2,nD4-dichlorophenyl)-probionitrile 57.- 2-(2-7luol7enyl)NO4O:-3
-imidazole-1-i 1.5280 l)-2-
Methoxypropionitrile 58.2-ethoxy2-(2-ph ND48:luol7enyl)-3-(i 1.5187midazole-1
-yl)-probionitrile 59.2-allyloxy-2-(2nD40: -7-fluorophenyl)-3- 1.5258(imidazo→leyl-yl)-probionitrile 60.2-allyloxy-2-(4 Melting point: -fluorophenyl)-3-159-16(imidazo-1-yl) (decomposition)-probionitrile, hydrogen nitrate 61.2-ethoxy 2-(4-7 fluor7enyl)-3-(imidazo -1-yl)-probionitrile, hydrogen nitrate 62.2-(4-fluorophenyl)-3-(imidazol-1-yl)-2-methoxypropionitrile, hydrogen nitrate 63.2- Ethoxy-2-(4-fluorophenyl)-3-(imidazo-1-yl)-probionitrile 64.2-(4-fluorophenyl)-3-(imidazo-1-yl)-2-methoxyprobionitrile Pionitrile 65.2-Allyloxy-2-(4-fluor-7enyl)-3-(imidazo-l-1-yl)-probionitrile66.2-decyloxy-3-(imidazonol-1-yl)-2 Melting point: 182 -184℃ (decomposition) Melting point: 194-196℃ (decomposition) Melting point: 54-5'RC Melting point: 88℃ 40・ND・1.5219 Melting point: 126-128℃ Compound name Physical constant -7enyl-probionitrile, Niryo hydrogen salt 67.2-(3,3-dimethylptoxy)-3-(imidazo-1-yl)-2-phenyl-propionitrile, hydrogen nitrate 68.3-(imidazo-1-yl) -2-octyloxy-2- phenylpropionitrile 69.2-(3,3-dimethoxyptoxy)-3-imidazol-1-yl)-2-phenylpropionitrile 70.2-(4- Bromphenyl)-2-propoxy-3-(imidazo-1-yl)-probionitrile, hydrogen nitrate 71.2-(4-brom7enyl)-3-(imidazo-1-yl)-2-propoxy Propionitrile, hydrogen nitrate 72.2-(4-bromphenyl)-12-hexyloxy-3-imidazol-1-yl)bionitrile, hydrogen salt 73.3-(imidazol-1-yl) -yl)-2-(2-methyl7enyl)-2-proboxypropionitrile, hydrogen nitrate 74.2-hexyloxy-3-(imidazo-1-yl)-2-(2-methylphenyl) -Probionitrile, hydrogen nitrate 75.2-(4-brom7enyl) -2-ptoxy3-(. (imidazol-1-yl)-probionitrile 76.2-(4-brom7enyl) (decomposition) Melting point: 195-198℃ (decomposition) 40● ND・nD゜15 Melting point: 171-174℃ (decomposition) Melting point: 162-1 Denku (decomposition) Melting point: 135-138℃ (decomposition) Melting point: 180-183℃ (decomposition) Melting point: 170-17? (Decomposition) 40. ND 1.5405 40 ND Oxy-3-(imidazo-1-yl)-probionitrile78.2-Ptoxy-3-(imidazo-1-yl)-2-(2-methyl7enyl)-probionitrile79.2-Ptoxy3-( imidazo-1-yl)-2-(2-methyl-7enyl)-probionitrile, hydrogen nitrate 80.2-hexyloxy-3-(imidazo-1-yl)-2-(2-methylphenyl) - Probionitrile 81.2-decyloxy-3-(imidazol-1-yl)-2 -7enylpropionitrile 82.3-(imidazol-1-yl)-2-(2-methylphenyl)-2 -Propoxypropionitrile 83.2-Ptoxy2-(3-chlorophenyl)-3-(imidazo-1-yl)-probionitrile84.2-(3-Chlorphenyl)-12-hexyloxy-3- (Imidazol-1-yl) -Probionitrile, hydrogen nitrate 85.2-decyloxy-31 (Imidazol-1-yl) -2-(2-methylphenyl) -Probionitrile, nitric acid water 40.ND. 1.5274 40・ND・1.5248 Melting point: 184-18 (range) 40● ND・1.5163 40enD・1.5020 40・ND・1.5276 40・ND・1.5282 Melting point: 162-165℃ (Decomposition) Melting point: 151-155°C (Decomposition) Compound name salt 86.3-(imidazole-1-yl)-2-(2-methylphenyl)-2-octyloxy-propionitrile 87.2-denruoxy-3 -(Imidazol-1-yl)-2-(2-methylphenyl)-probionitrile 88. 2-(imidazol-1-inolyl)-2-(4-methoxyferal)-probionitrile, nitric acid Hydrogen salt 89.2-Ptoxy-3-(imidazo-1-yl)-2-(4-methoxyphenyl)-probionitrile 90.2-(4-chlor7enyl)-2-hexynoleoxo-3-( (imidazol-1-yl) -probionitrile, hydrogen nitrate 91.2-(4-chlorophenyl) 12-hexyloxy-3-(imidasol-1-yl) -probionitrile, hydrogen nitrate Physical constant 40. ND・40・ND・1.5139 Melting point: 163-167℃ (decomposition) 40● ND● 1.522-8 Melting point: 195-197℃ (decomposition) Melting point: 158-163℃ (decomposition) Used as starting material 3-aryl- or 3-alkylsulfonyloxy-propionitriles of the general formula (2), in which Y represents an aryl- or alkylsulfonyloxy group, have not been described in publications to date.

This aryl or alkylsulfonyloxy compound of the general formula : Hess et al., 66?R.
dt. chem. αS 8th Edition, page 394, 1917
2, 2004), phenylacetonitrile represented by the general formula (1): [wherein Z and R represent the above] is hydroxymethylated by a method known per se,
The thus obtained 3-hydroxyprobionitrile represented by the general formula (1): [wherein Z and R represent the above] is optionally mixed with a suitable sulfonic acid derivative such as sulfonic acid chloride. Obtained by reaction in the presence of an acid binder.

Hydroxymethyl compounds of the general formula (2) are not yet known in the literature. 3-halogen-propionitrile of the general formula (1) in which Y represents a halogen atom, which is known from publications, can be obtained by reacting the phenylacetonitrile of the general formula (2) with dihalogenmethane by a method known per se. It will be done.

Next, the preparation of the initiator composition will be described.

3-Methylsulfonyl-2-phenyl-2-propoxypropionitrile 2-phenyl-2-propoxyacetonitrile. 27g (0.154mol) of pyridine
Dissolve in 20 ml of rose formaldehyde and add 1 ml of rose formaldehyde to this solution.
Add 8.5 g (0.614 mol).

7.7 ml of tetrabutylammonium hydroxide (TBAOH) was added to this suspension under ice cooling, and 1'Nj
I! Stir vigorously for a while. This anti. The reaction mixture is poured into ice water and extracted twice with ether. The ether phase is then washed twice with aqueous sodium chloride solution and dried over magnesium sulfate. After removing the desiccant and concentrating in vacuo,
A colorless oil remains, which is found to be homogeneous by thin-layer chromatography and can be processed further without further purification. Yield: 2
8.4 g = 90% of theory 3-Hydroxy-2-phenyl-2-propoxypropionitrile The 3-hydroxy-2-phenyl-2-
28 g (0.136 mol) of propoxypropionitrile are dissolved in 200 ml of toluene and 19.5 g (0.171 mol) of methanesulfonic acid chloride are added to this solution.

18.6 g of triethiamine at 100C (a). 184 mol) is added dropwise.

This solution was further stirred three times at room temperature, and the precipitated triethylamine hydrochloride was filtered out and concentrated. The residue is taken up in ether and the solution is washed with dilute HCe solution, water, sodium bicarbonate solution and twice again with water. The solution is dried over magnesium sulfate, the desiccant is filtered off with suction and concentrated. This oily residue is dried in vacuo. This oily residue is found to be pure by thin layer chromatography. yield:
32.27 g = 86% of theory ND = 1.5000 3-Methylsulfonyl-2-phenyl-2-propoxypropionitrile The following examples show compounds according to the invention carried out in the form of the preparations described above. Used to detail the usage of.

Example 3 Barley Helmintosporium Speck (Helmi)
nthOspOriumspec. ) on the effects of seed treatments.

HelminthOspOriumgr'Amine
Seeds of barley naturally diseased by A. urrl) were untreated or treated as described in the table, sown in pots with soil and germinated at temperatures below +16°C.

After germination, the shoots were irradiated with artificial light for 1 hour every day. After approximately 5 weeks, all germinated and fungal diseased plants were counted for each test group. The fungicidal activity was calculated as follows: the compound is present as a 20% spray powder.

Comparative drug Methoxyethyl-Hg monosilicate 2.6387 Example 4 Cucurbitaceae plant Erysiphe CiChOraCearUTTl in greenhouse
Effect of preventive foliage treatment on.

Young seedlings of Cucurbitaceae plants, which had been sprayed with the above-mentioned concentration of active ingredient until dripping, were treated with ErysiphecichOracearum after the spray coating had dried.
um) by spraying with dry downy mildew spores and inoculated with untreated control plants in a greenhouse for 2 hrs.
Maintain constant temperature at 4℃.

After one week, the affected downy mildew area was evaluated as a percentage of the total foliage area.

The fungicidal activity was calculated as follows: 100·morbidity of treated 4 100− = % fungicidal activity Morbidity when untreated The material was formulated as a 20% spray powder.

) Example 5 Pyricularia oryzae on rice seedlings in a greenhouse (
Effect of foliage treatment on Piricularia Oryzae).

Rice seedlings were sprayed until dripping with the active substance concentrations listed in the table. After the spray coating had dried, the treated and untreated control plants were infected with the stem spot pathogen (Blatt).
fleckerlerreger) Piricularia ●Spores of Piricularia Oryzae (
The cells were inoculated by spraying with a suspension of about 200,000/ml), moistened and kept at constant temperature in a greenhouse at +25°C to +2TC. After 5 days, it was determined what percentage of the stem and leaf area was infected.

From this morbidity, the fungicidal action was calculated as follows: The substance was formulated as a 20% spray powder.

Example 6 Tomato Botrytis cinerea (BOt) in a greenhouse
Effect of prophylactic foliar treatments on rytiscinerea).

Tomato seedlings were sprayed until dripping with the active substance concentrations listed in the table.

After the spray coating has dried, the treated and untreated plants are treated with the botrytis pathogen Botrytis Cinerea (BOtr″Y).
Tiscir! Erea) spores (approximately 100,000 caps/
The seeds were inoculated by spraying with a suspension of fruit juice solution (ml), moistened and kept constant at about 20° C. in a greenhouse. After destroying the untreated plants (=100% morbidity), the morbidity of the treated plants was determined. The fungicidal action was calculated as follows: the compound according to the invention was present as a 20% formulation.

Example 7 Plasmopara of grapes in a greenhouse Viticola (P
Effect of prophylactic foliar treatments on lasmOparaviticOla).

Grape seedlings with approximately 5 to 8 leaves are sprayed with drippings at the concentration described, and after the spray film has dried, an aqueous suspension of sporangia of the fungus (approximately 200(1) sporangia/ml) is applied. The underside of the leaves was sprayed with the suspension, and the temperature was immediately maintained in a greenhouse at 22-24° C. in an atmosphere as saturated with water vapor as possible.

On the second day, the air humidity was returned to normal height (30-70% saturation) for 3-4 days and then held at water vapor saturation for 1 day.

Subsequently, the % area diseased by fungi from each leaf was recorded and the average per treatment was calculated to determine the fungicidal action as follows: The substance was formulated as a 20% spray powder. did. EXAMPLE 8 In the laboratory, sagebrush was treated with a 5-aqueous emulsion of the drug according to the invention.

The concentration of active substance in the emulsion was 100 ppm.

A glass slide was placed for this purpose in a 200 ml glass tube containing 10 ml of active substance emulsion. A piece of paper was placed on top of this glass slide. This door paper was impregnated with the solution, and then w seeds of Porphyra spp. were evenly distributed thereon. A Petri dish lid was then placed over the tube. Two glass tubes were prepared for each substance. For evaluation, the lengths of stems, leaves and roots were measured 7 days after germinated seeds.

In the table, values are given in relation to the control and are given as percentage values.

It has been found that the compounds according to the invention exert a significant effect on root and foliage growth in the case of Porphyra.

This is evident in the demand rate (>100%) or rejection rate (<100%) of the individual parts. Example 9 Cotton was grown under greenhouse conditions to the embryonic stage (Keimblatts-TadiUr!1).

The compounds according to the invention were added to 1 kg of active substance/Ha and 2 k9
The plants were sprayed at a usage rate of /Ha.

After 3 weeks of spraying, the total length of the plants and the length of the first internode were measured.

In the table, the results are stated in the form of percentage values compared to the control. Generally, the reduction in growth is more significant than that of the comparison specimen.

Example 10 Erysiphae graminis (Er), a grain downy mildew fungus of barley
Effect of seed treatments on Aminis xsiphegr'Aminis).

Summer barley seeds untreated or active substance 100g
/100k9, sown in pots with soil, and germinated in a greenhouse at a temperature of approx.

After the formation of the first foliage, the plants were inoculated by rubbing against plants infected with downy mildew. After one week, the percentage of the stem and leaf area covered by downy mildew was recorded.

Fungicidal activity was calculated as follows: 100-10
0°f:'A') = % Fungicidal Activity Morbidity in case of untreatment Incompatibility with case of treatment was evaluated after germination of the plants.

This evaluation was carried out according to the following criteria: The compound according to the invention was present as a spray content with an active substance content of 20%.

Unlike the comparative drugs, the compounds according to the invention
) as well as being completely compatible with barley.

Example 11 Brown spot disease of sugar beetroot (Betabul girls) (Cercospora
a? Effect of prophylactic foliar treatments on TIcOIa)).

Sugar beets with 4 well-grown leaves were sprayed at the stated concentration until dripping.

After the spray coating has dried, the treated and untreated control plants are infected with Cercospora (CercOspOra) - Spore 1
A suspension of 5000 particles/Mt was uniformly sprayed. 2 plants
The temperature was maintained in a greenhouse for 4 days at 6°C and water vapor saturated air, followed by an additional 10 days in the greenhouse at approximately 27C. The percentage of diseased stem and leaf area was then recorded. The fungicidal activity was then calculated as follows:) Example 12 Inhibition of fungal growth of nutrient solutions.

20 ml of a nutrient solution consisting of grape juice and water (1:1) were placed in a 100 ml flask, to which the powdered active substance preparation was added.

Subsequently, this solution was mixed with Penicillium digitum (Pen
conidia (spores) of icilljdigltatum
was inoculated. After a treatment time of 5 days at ~24°C, fungal development on the nutrient solution surface was evaluated. Rating: 0 = No fungal growth 1 = Individual fungal colonies on surface 2 = 5-10% of surface area covered by fungal areas 3 = 10-30% of surface area covered by fungal areas 4 = 30-60% of surface area
5 = 60-100% of the surface area is covered by the fungi-infested area. The active substance concentration of the nutrient solution and the result are:
They are listed in the table below.

Comparative drug (according to West German Patent Publication No. 2604047) 3-(imidazol-1-yl)-2-phenyl-2-butylpropionitrium Downy mildew fungus Uncinula
Effect of prophylactic foliage treatment on uIanacatOr).

The cultivar Silvana has about 8-10 leaves.
Seedlings of Cormorant ner) were sprayed with the dropwise wet method at the concentrations listed in the table.

After drying the spray coating, the plants were dry-sprayed with conidia of the fungus UncinulanecatOr and kept thermostatically in a greenhouse for 12 days at approximately n°C.

The proportion of the foliage area diseased by downy mildew was then evaluated as a percentage and the fungicidal activity was calculated as follows: The morbidity reached 88.3% in the untreated case.

The drug was present as a 20% atomized powder. You can know the evaluation from the table. Example 14 Apple spot disease fungus Benzulia inaequalis (V
Effect of prophylactic foliar treatments on C. enturiainaequalis.

Young, vegetative apple shoots of variety MMlO6 were treated with an active substance concentration of 0.1% until they dripped.

After the spray coating dries, conidia (330,000/ml
) was sprayed onto the foliage, and the young shoots were subsequently covered with polyethylene bags and infected with fungi under semi-shade for 3 days. The bag was then removed. After a total test time of 2112 weeks, the proportion of area diseased by the bacterium was evaluated as a percentage. Untreated controls showed 99% morbidity. The results of the treatment were calculated as follows: The compound was present as a 20% atomized powder.

．． ? ◆” Todoroki F? ” L crow? A5●---
- Example 15 Effect of curative foliage treatment on apple spot disease fungus Venturiainaequalls in open field.

Young buds of apples of cultivar MMlO6 were sprayed with a suspension of conidia (33000 C@/ml) and immediately kept moist by covering with polyethylene bags.

Plants were placed under semi-shade. After 3 days, the bag was removed.

Seven days after inoculation, the plants were treated with an active substance concentration of 0.1% until dripping. After a further 1112 weeks, the plants were infected with apple spot fungus and the left stem and leaf area was evaluated as a percentage. The percentage was 99% in the untreated case. The compound according to the invention was present as a 20% atomized powder. The effect of the treatment was calculated as follows: comparative agent 2-butyl-3-(imidazol-1-yl)-2-phenylpropionitrile, hydrogen nitrate.
90 Example 16 Preventive foliage treatment against Erysiphegr'Aminjs of barley.

Barley at the first foliage stage was sprayed in the drip wet method at the stated active substance concentration with the addition of alkaryl polyglycol ether as wetting agent (0.05%).

After the spray coating had dried, the plants and untreated control plants were evenly rubbed with downy mildew-infected grains and then kept at constant temperature in a greenhouse for 1 week at 20-2 generations. Continuing,
Average downy mildew morbidity was recorded per pot (18-20 plants). The fungicidal action was calculated according to the following formula: The substance according to the invention was present as a 20% formulation.

Example 17 Uromyces Apendiculatus (UrOmy
cesappfrldiculatus (bean mildew fungus).

100pp of kidney beans at the primary stem and leaf stage grown for half a day
It was sprayed until dripping at an active substance concentration of m.

After the spray coating has dried, the treated and untreated control plants are infected with Uromyces apendichulatus (UrOmyce
sappendicu Iatus). The plants were then incubated for 2 days at 27C in a humid room and subsequently maintained at approximately 20C under greenhouse conditions.
Eleven days after spraying with spores, P. pyogenes were counted (an average of 2 per leaf for untreated controls). The fungicidal action was calculated as follows: the substance according to the invention
It was present as a 20% formulation and showed more than 90% fungicidal activity.

Example 18 HelminthOspOriumteres (=
PyrenOphOratere
s), Effect of preventive foliage treatment on net spot disease of barley.

Barley seedlings at the first foliage stage were sprayed dripping at the concentrations listed.

After the spray coating has dried, treated plants and untreated control plants are infected with Helmintsporium teres (Helmint terres).
hOspOriurrlteres) and cultured for 2 days at 20-27C in a humid room. One week after inoculation, the percentage morbidity of the foliage area was recorded. The fungicidal activity was calculated as follows: the compound was present as a 20% formulation.

Example 19 Puccinia hordelii (PucciniahOrdelii), a fungus causing mildew of barley in a plant growth room with controlled temperature and humidity.
Effect of preventive foliage treatment on ).

Barley seedlings at the first foliage stage were sprayed at the stated concentration until dripping. After the spray coatings had dried, treated plants and untreated control plants were inoculated by rubbing the plants infected with Mildew and placed in a plant growth chamber. Plants were cultured for 10 days at 15° C. in mostly moisture-saturated air for the first two days.

Thereafter, the percentage of leaf area affected by rust was recorded as a percentage. The fungicidal activity was calculated as follows: the compound was present as a 20% formulation.

The table demonstrates the good to very good effect of a number of the compounds according to the invention. Example 20 Yellow rot fungi of barley in a temperature- and humidity-controlled plant growth chamber.
Effect of prophylactic foliar treatments on riifOrmjs).

Barley seedlings were sprayed dripping at the stated concentration at the first foliage stage.

After the spray coating has dried, the treated and untreated plants are coated with Puccinia striiformis (Pucc) in 1,1,2-trifluor-1,2,2-trichloroethane.
The plants were sprayed with a suspension of summer spores of C. iniastriifOrmis and kept at a constant temperature of 150°C in a plant growth chamber.

For the first two days, almost moisture-saturated air was obtained. 1
After 5 days, the percentage of stem and leaf area affected by rust was recorded.

The fungicidal activity was calculated as follows: Example 21 HelminthOspOri of barley in a temperature-controlled plant growth chamber.
umsativum).

HelminthOspOriumsativum
50 g/100 k9 of the active substance of the drug according to the invention were applied to barley seeds which had been artificially infested by .

6.5 treated or untreated seeds for each test group.
The seeds were sown in ×6.5G plastic pots. Sand was used as the soil. Each test group was repeated twice. This pot was placed in a plant growth chamber at 15°C. After 4 weeks, the germinated plants were tested for percent stem disease.

From the average of the repeats, the fungicidal action was calculated as follows: The drug according to the invention was present as 20% of the formulation.

Example 22 In vitro, pea oil spot disease (Fettflecken)
The pathogen of Pseudomonas (Krankheit)
cOla).

The raw malt agar was cooled to approximately 45° C. after thermal esterification, then the test substances in an aqueous preparation were mixed and poured into plastic Petri dishes.

After solidification of the culture medium, dishes with treated agar and dishes with untreated agar as a control were infected with the oil spot pathogen Pseudomonas onaspha.
seOllcOla) in the center of the inoculation ring. The dish was then kept at a constant temperature of 22'C. 2112
After a week, the radius of the bacterial colony was measured.

From the average of two replicates per test group, the bacterial mastication effect was calculated as follows: Compounds were present as 20% formulation.

Pseudomonas phaseolycola (PSeU(10m0naSphase011c01a
) of 250 ppm of active substance in agar
.

Example 23 Effect of preventive foliage treatment against the downy mildew fungus Erysiphegraminis of barley in a greenhouse.

Barley seedlings at the first foliage stage were sprayed at the indicated concentrations until dripping.

After the spray coating had dried, the treated plants and untreated control plants were inoculated with dried downy mildew spores by rubbing the diseased plants on the test plants. Thereafter, the test plants were kept at a constant temperature of about 20 to 27 C in a greenhouse, and one week later, the disease rate of the stem and leaf area was evaluated as a percentage. The fungicidal activity was calculated as follows: the compound was present as a 20% formulation.

Claims (1)

[Claims] 1 General formula I: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ I [In the formula, R is a halogen atom, (C_1-C_4)-alkyl group,
(C_1-C_4)-alkoxy group, (C_1-C_4
)-represents the same or different aromatic hydrocarbon radicals which may be substituted one or more times by an alkylthio group, a trifluoromethyl group or a nitro group, and R_1 is (
C_1-C_1_0)-alkyl group, (C_3-C_8
)-alkenyl group, (C_3-C_8)-alkynyl group, or halogen atom, (C_1-C_4)-alkyl group, (C_1-C_4)-alkoxy group, (C_
1 to C_4)-representing the same or different phenylalkyl group which may be substituted one or more times by an alkylthio group, a trifluoromethyl group or a nitro group] and their Acid addition salts with inorganic and organic acids. 2 R is a halogen atom, (C_1-C_4)-alkyl group, (C_1-C_4)-alkoxy group, (C_1-C
_4) optionally substituted one or more times with an alkylthio group, trifluoromethyl group or nitro group,
represent the same or different phenyl groups, and R_1 is (C_
1-C_6)-alkyl group, allyl group, propalkyl group, or halogen atom, (C_1-C_4)-alkyl group, (C_1-C_4)-alkoxy group, (C_
1-C_4)-Imidazolyl- as claimed in claim 1, representing the same or different benzyl radicals, which may be substituted one or more times by an alkylthio group, a trifluoromethyl group or a nitro group. Propionitrile. 3 3-(imidazol-1-yl)-2-phenyl-
The compound according to claim 1, which is 2-propoxy-propionitrile, hydrogen nitrate. 4 3-(imidazol-1-yl)-2-phenyl-
A compound according to claim 1 which is 2-propoxy-propionitrile. 5 2-butoxy-3-(imidazol-1-yl)-
The compound according to claim 1, which is 2-phenyl-propionitrile, hydrogen nitrate. 6 2-Butoxy-3-(imidazol-1-yl)-
A compound according to claim 1 which is 2-phenyl-propionitrile. 7. The compound according to claim 1, which is 2-allyloxy-3-(imidazol-1-yl)-2-phenyl-propionitrile, hydrogen nitrate. 8. The compound according to claim 1, which is 2-allyloxy-3-(imidazol-1-yl-)-2-phenyl-propionitrile. 9 2-ethoxy-3-(imidazol-1-yl)-
2-phenyl-propionitrile, hydrogen nitrate;
A compound according to claim 1. 10 2-ethoxy-3-(imidazol-1-yl)
2. A compound according to claim 1, which is -2-phenyl-propionitrile. 11 The compound according to claim 1, which is 3-(imidazol-1-yl)-2-methoxy-2-phenyl-propionitrile, hydrogen nitrate. 12 The compound according to claim 1, which is 3-(imidazol-1-yl)-2-methoxy-2-phenyl-propionitrile. 13 2-(2-chlorophenyl)-3-(imidazol-1-yl)-2-propoxy-propionitrile,
The compound according to claim 1, which is a hydrogen nitrate salt. 14 2-butoxy-2-(4-chlorophenyl)-3
-(imidazol-1-yl)-propionitrile, hydrogen nitrate, the compound according to claim 1. 15 2-butoxy-2-(2-chlorophenyl)-3
-(imidazol-1-yl)-propionitrile, hydrogen nitrate, the compound according to claim 1.
16 2-allyloxy-2-(2-chlorophenyl)
-3-(imidazol-1-yl)-propionitrile, hydrogen nitrate, the compound according to claim 1. 17 The compound according to claim 1, which is 2-(4-chlorophenyl)-3-(imidazol-1-yl)-2-propoxy-propionitrile, hydrogen nitrate. 18 2-allyloxy-2-(4-chlorophenyl)
-3-(imidazol-1-yl)-propionitrile, hydrogen nitrate, the compound according to claim 1. 19 The compound according to claim 1, which is 2-(2-chlorophenyl)-3-(imidazol-1-yl)-2-propoxy-propionitrile. 20 2-butoxy-2-(4-chlorophenyl)-3
-(imidazol-1-yl)-propionitrile. The compound according to claim 1, which is -(imidazol-1-yl)-propionitrile. 21 2-butoxy-2-(2-chlorophenyl)-3
-(imidazol-1-yl)-propionitrile. The compound according to claim 1, which is -(imidazol-1-yl)-propionitrile. 22 2-allyloxy-2-(2-chlorophenyl)
-imidazol-1-yl)-propionitrile. 23 The compound according to claim 1, which is 2-(4-chlorophenyl)-3-(imidazol-1-yl)-2-propoxy-propionitrile. 24 2-allyloxy-2-(4-chlorophenyl)
-3-imidazol-1-yl)-propionitrile. 25 2-benzyloxy-3-(imidazole-1-
2-phenyl-propionitrile, hydrogen nitrate. 26 2-benzyloxy-3-(imidazole-1-
2-phenyl-propionitrile. 27 The compound according to claim 1, which is 3-(imidazol-1-yl)-2-isopropyloxy-2-phenyl-propionitrile, hydrogen nitrate. 28 3-(imidazol-1-yl)-2-isopropyloxy-2-phenyl-propionitrile,
A compound according to claim 1. 29 The compound according to claim 1, which is 2-(4-chlorophenyl)-2-hexyloxy-3-(imidazol-1-yl)-propionitrile, hydrogen nitrate. 30 The compound according to claim 1, which is 2-(4-chlorophenyl)-2-hexyloxy-3-(imidazol-1-yl)-propionitrile. 31 The compound according to claim 1, which is 2-allyloxy-3-(imidazol-1-yl)-2-(2-methylphenyl)-propionitrile, hydrogen nitrate. 32 The compound according to claim 1, which is 2-(3,4-dichlorophenyl)-3-(imidazol-1-yl)-2-propoxy-propionitrile, hydrogen nitrate. 33 The compound according to claim 1, which is 2-butoxy-2-(2,4-dichlorophenyl)-3-(imidazol-1-yl)-propionitrile, hydrogen nitrate. 34 The compound according to claim 1, which is 2-allyloxy-2-(2,4-dichlorophenyl)-3-(imidazol-1-yl)-propionitrile, hydrogen nitrate. 35 The compound according to claim 1, which is 2-ethoxy-2-(3,4-dichlorophenyl)-3-(imidazol-1-yl)-propionitrile, hydrogen nitrate. 36 The compound according to claim 1, which is 2-allyloxy-3-(imidazol-1-yl)-2-(2-methylphenyl)-propionitrile. 37 The compound according to claim 1, which is 2-(3,4-dichlorophenyl)-3-(imidazol-1-yl)-2-propoxy-propionitrile. 38 The compound according to claim 1, which is 2-allyloxy-2-(3,4-dichlorophenyl)-3-(imidazol-1-yl)-propionitrile. 39 The compound according to claim 1, which is 2-butoxy-2-(2,4-dichlorophenyl)-3-(imidazol-1-yl)-propionitrile. 40 The compound according to claim 1, which is 2-allyloxy-2-(2,4-dichlorophenyl)-3-(imidazol-1-yl)-propionitrile. 41 The compound according to claim 1, which is 2-ethoxy-2-(3,4-dichlorophenyl)-3-(imidazol-1-yl)-propionitrile. 42 3-(imidazol-1-yl)-2-phenyl-2-(1,2,2-trimethyl-propoxy)-propionitrile, hydrogen nitrate, Claim 1
Compounds described in Section. 43 The compound according to claim 1, which is 3-(imidazol-1-yl)-2-(2-methoxy-ethoxy)-2-phenyl-propionitrile, hydrogen nitrate. 44 The compound according to claim 1, which is 2-(2,2-dimethylpropoxy)-3-(imidazol-1-yl)-2-phenyl-propionitrile, hydrogen nitrate. 45 2-(2,2-dimethyl-propoxy)-3-(
2. The compound according to claim 1, which is imidazol-1-yl)-2-phenyl-propionitrile. 46 The compound according to claim 1, which is 2-(2-fluorophenyl)-3-(imidazol-1-yl)-2-propoxy-propionitrile, hydrogen nitrate. 47 2-butoxy-2-(2-fluorophenyl)-
3-(imidazol-1-yl)-propionitrile,
The compound according to claim 1, which is a hydrogen nitrate salt. 48 The compound according to claim 1, which is 2-(4-fluorophenyl)-3-(imidazol-1-yl)-2-propoxy-propionitrile, hydrogen nitrate. 49 2-butoxy-2-(4-fluorophenyl)-
3-(imidazol-1-yl)-propionitrile-
The compound according to claim 1, which is a hydrogen nitrate salt. 50 The compound according to claim 1, which is 2-allyloxy-2-(2-fluorophenyl)-3-(imidazol-1-yl)-propionitrile, hydrogen nitrate. 51 2-ethoxy-2-(2-fluorophenyl)-
3-(imidazol-1-yl)-propionitrile,
The compound according to claim 1, which is a hydrogen nitrate salt. 52 2-(2-fluorophenyl)-3-(imidazol-1-yl)-2-methoxy-propionitrile,
The compound according to claim 1, which is a hydrogen nitrate salt. 53 The compound according to claim 1, which is 3-(imidazol-1-yl)-2-phenyl-2-(1,2,2-trimethyl-propoxy)-propionitrile. 54 The compound according to claim 1, which is 3-(imidazol-1-yl)-2-(2-methoxy-ethoxy)-2-phenylpropionitrile. 55 The compound according to claim 1, which is 2-(2-fluorophenyl)-3-(imidazol-1-yl)-2-propoxy-propionitrile. 56 2-butoxy-2-(2-fluorophenyl)-
A compound according to claim 1 which is 3-(imidazol-1-yl)-propionitrile. 57 The compound according to claim 1, which is 2-(4-fluorophenyl)-3-(imidazol-1-yl)-2-propoxy-propionitrile. 58 2-butoxy-2-(4-fluorophenyl)-
A compound according to claim 1 which is 3-(imidazol-1-yl)-propionitrile. 59 The compound according to claim 1, which is 2-(2-fluorophenyl)-3-imidazol-1-yl)-2-methoxy-propionitrile. 60 2-ethoxy-2-(2-fluorophenyl)-
A compound according to claim 1 which is 3-(imidazol-1-yl)-propionitrile. 61 The compound according to claim 1, which is 2-allyloxy-2-(2-fluorophenyl)-3-(imidazol-1-yl)-propionitrile. 62 The compound according to claim 1, which is 2-allyloxy-2-(4-fluorophenyl)-3-(imidazol-1-yl)-propionitrile, hydrogen nitrate. 63 2-ethoxy-2-(4-fluorophenyl)-
3-(imidazol-1-yl)-propionitrile,
The compound according to claim 1, which is a hydrogen nitrate salt. 64 2-(4-fluorophenyl)-3-(imidazol-1-yl)-2-methoxy-propionitrile,
The compound according to claim 1, which is a hydrogen nitrate salt. 65 2-ethoxy-2-(4-fluorophenyl)-
A compound according to claim 1 which is 3-(imidazol-1-yl)-propionitrile. 66 The compound according to claim 1, which is 2-(4-fluorophenyl)-3-(imidazol-1-yl)-2-methoxy-propionitrile. 67 The compound according to claim 1, which is 2-allyloxy-2-(4-fluorophenyl)-3-(imidazol-1-yl)-propionitrile. 68 The compound according to claim 1, which is 2-decyloxy-3-(imidazol-1-yl)-2-phenyl-propionitrile, hydrogen nitrate. 69 The compound according to claim 1, which is 2-(3,3-dimethylbutoxy)-3-(imidazol-1-yl)-2-phenyl-propionitrile, hydrogen nitrate. 70 The compound according to claim 1, which is 3-(imidazol-1-yl)-2-octyloxy-2-phenyl-propionitrile. 71 The compound according to claim 1, which is 2-(3,3-dimethoxybutoxy)-3-imidazol-1-yl)-2-phenyl-propionitrile. 72 2-(4-bromphenyl)-2-butoxy-3
-(imidazol-1-yl)-propionitrile, hydrogen nitrate, the compound according to claim 1. 73 2-(4-bromphenyl)-3-(imidazol-1-yl)-2-propoxy-propionitrile,
The compound according to claim 1, which is a hydrogen nitrate salt. 74 The compound according to claim 1, which is 2-(4-bromphenyl)-2-hexyloxy-3-imidazol-1-yl)-propionitrile, hydrogen nitrate. 75 3-(imidazol-1-yl)-2-(2-methylphenyl)-2-propoxy-propionitrile,
The compound according to claim 1, which is a hydrogen nitrate salt. 76 2-hexyloxy-3-(imidazole-1-
The compound according to claim 1, which is hydrogen nitrile)-2-(2-methylphenyl)-propionitrile. 77 2-(4-bromphenyl)-2-butoxy-3
-(imidazol-1-yl)-propionitrile. The compound according to claim 1, which is -(imidazol-1-yl)-propionitrile. 78 The compound according to claim 1, which is 2-(4-bromphenyl)-3-(imidazol-1-yl)-2-propoxy-propionitrile. 79 The compound according to claim 1, which is 2-(4-bromphenyl)-2-hexyloxy-3-(imidazol-1-yl)-propionitrile. 80 2-butoxy-3-(imidazol-1-yl)
The compound according to claim 1, which is -2-(2-methylphenyl)-propionitrile. 81 2-butoxy-3-(imidazol-1-yl)
The compound according to claim 1, which is -2-(2-methylphenyl)-propionitrile, hydrogen nitrate. 82 2-hexyloxy-3-(imidazole-1-
2-(2-methylphenyl)-propionitrile. 83
2-decyloxy-3-(imidazol-1-yl)-
A compound according to claim 1 which is 2-phenyl-propionitrile. 84 The compound according to claim 1, which is 3-(imidazol-1-yl)-2-(2-methylphenyl)-2-propoxy-propionitrile. 85 2-butoxy-2-(3-chlorophenyl)-3
-(imidazol-1-yl)-propionitrile. The compound according to claim 1, which is -(imidazol-1-yl)-propionitrile. 86 The compound according to claim 1, which is 2-(3-chlorophenyl)-2-hexyloxy-3-(imidazol-1-yl)-propionitrile, hydrogen nitrate. 87 The compound according to claim 1, which is 2-decyloxy-3-(imidazol-1-yl)-2-(2-methylphenyl)-propionitrile, hydrogen nitrate. 88 The compound according to claim 1, which is 3-(imidazol-1-yl)-2-(2-methylphenyl)-2-octyloxy-propionitrile. 89 The compound according to claim 1, which is 2-decyloxy-3-(imidazol-1-yl)-2-(2-methylphenyl)-propionitrile. 90 2-butoxy-3-(imidazol-1-yl)
-2-(4-methoxyphenyl)-propionitrile,
The compound according to claim 1, which is a hydrogen nitrate salt. 91 2-butoxy-3-(imidazol-1-yl)
The compound according to claim 1, which is -2-(4-methoxyphenyl)-propionitrile. 92 The compound according to claim 1, which is 2-(4-chlorophenyl)-2-hexyloxy-3-(imidazol-1-yl)-propionitrile, hydrogen oxalate. 93 The compound according to claim 1, which is 2-(4-chlorophenyl)-2-hexyloxy-3-(imidazol-1-yl)-propionitrile, hydrogen sulfate. 94 General formula I: ▲There are mathematical formulas, chemical formulas, tables, etc.▼ I [In the formula, R is a halogen atom, (C_1-C_4)-alkyl group,
(C_1-C_4)-alkoxy group, (C_1-C_4
)-represents the same or different aromatic hydrocarbon radicals which may be substituted one or more times by an alkylthio group, a trifluoromethyl group or a nitro group, and R_1 is (
C_1-C_1_0)-alkyl group, (C_3-C_8
)-alkenyl group, (C_3-C_8)-alkynyl group, or halogen atom, (C_1-C_4)-alkyl group, (C_1-C_4)-alkoxy group, (C_
1 to C_4)-representing the same or different phenylalkyl group optionally substituted one or more times by an alkylthio group, a trifluoromethyl group or a nitro group] In the method, general formulas include: ▲ Numerical formulas, chemical formulas, tables, etc. [representing an oxy- or arylsulfonyloxy group] is reacted with an imidazole represented by the formula: ▲ Numerical formula, chemical formula, table, etc. ▼ in the presence of a solvent and in some cases a base. A method for producing imidazolyl-propionitrile of general formula I, characterized by comprising: 95 General formula: ▲Mathematical formula, chemical formula, table, etc.▼ I [In the formula, R is a halogen atom, (C_1-C_4)-alkyl group,
(C_1-C_4)-alkoxy group, (C_1-C_4
)-represents the same or different aromatic hydrocarbon radicals which may be substituted one or more times by an alkylthio group, a trifluoromethyl group or a nitro group, and R_1 is (
C_1-C_1_0)-alkyl group, (C_3-C_8
)-alkenyl group, (C_3-C_8)-alkynyl group, or halogen atom, (C_1-C_4)-alkyl group, (C_1-C_4)-alkoxy group, (C_
1 to C_4)-representing the same or different phenylalkyl group which may be substituted one or more times by an alkylthio group, a trifluoromethyl group or a nitro group] A disinfectant characterized by containing pionitrile. 96. The fungicide according to claim 95, which has fungicidal action. 97. The fungicide according to claim 95, which has a growth regulating effect. 98. The bactericidal agent according to claim 95, which has a bactericidal effect. 99. The disinfectant according to claim 95, which is mixed with a carrier and/or an auxiliary agent.