JPS588070A - Imidazolyl-propionitrile, manufacture and bactericide containing same - Google Patents

Abstract

(57) [Abstract] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel imidazolyl-propionitrile, a process for its production, and a fungicide containing this compound, which has a particularly fungicidal action.

Imidazolyl-zolobionitrile sieve conductors with a homicidal action are already known (fI DE 260 4 047). However, this compound has a relatively narrow spectrum of action and this is unsatisfactory.

The object of the present invention is to develop a new imidazolyl-propionitrile, which has a wide range of uses and a broad spectrum of carcincidal action, especially in the field of object protection. It is.

According to the invention, this problem is solved by the general formula I:N [wherein Rat halogen atom, <cx~04)-alkyl group, (
the same or different aromatic hydrocarbon radicals optionally substituted one or more times by c,~C,)-alkoxy, (C~c,)-alkylthio, trifluoromethyl or nitro groups; An expression.

R is (Cz~01°)-alkyl group, (Cs~C,)
-Alkenyl group % (05-C3)-Alkynyl group, parent is halo IF"y atom, (C'l-c,)-alkyl group, (C1-04)-alkoxy group, (C1<4)
-alkylthio group, trifluoromethyl group or =toJ
1 represents the same or different phenylalkyl radicals, which may be substituted one or more times.] and its acid addition salts with inorganic and organic acids.

It is surprising that this compound outperforms known active substances of the same structure and direction of action.

This fungicidal action is systematic in a wide variety of ways! The truth of the place tM'l
This is an astonishing increase for 14. 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, i.e. 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 protects this soil surface part against pathogens. do.

Other actions include growth regulating action and bactericidal action.

Due to the broad spectrum of action detected, this compound is suitable not only for the protection of cultivated plants, but also for the protection of substances and for the control of pathogenic and zoonotic microorganisms, including flies. This results in broadly differentiated usage.

Depending on the detailed meaning of the substituents, important fields of use can be obtained in this case, and the compounds exhibit interesting effects. The compounds can therefore be used in each case as a killicide, a plant growth regulator or a fungicide.

In the case of the compound represented by the general formula (■), the following can be exemplified: R2-fluorophenyl group, 3-fluorophenyl group,
4-fluorophenyl group, 2-chlorophenyl 13-chlorophenyl group, 4-chlorophenyl 12-bromphenyl group, 5-1'romphenyl M, 4-bromphenyl group, 2-larphenyl group, 5- =i meadophenyl, 4-g-dophel group, 2,6-dichlorophenyl f
, 2.4-dichloro7-enyl M, 5.4-dichlorophenyl 12.6-dichlorophenyl &, 2-methylphenyl 13-methylphenyl group, 4-methylphenyl group, 2
-ethylphenyl group, 3-ethylphenyl group, 4-ethylphenyl M, 2-7'ropylphenyl M, 5-f lopylphenyl group, 4-7'ropylphenyl group, 2-inozolobylphenyl f, 5- Isopropylphenyl group, 4-
Isopropylphenyl group, 2-butylphenyl group, 5-
Butylphenyl group, 4-butylphenyl group, 2-sec
-butylphenyl group.

5-ε・C-butylphenyl group, 4-5ea-defruphenyl group, 2-tert-ffruphenyl group,
5-tert-butylphenyl group, 4-tert-butylphenyl group, 2-methoxy71enyyes 5-methoxyphenyl group, 4-methoxyphenyl group, 2-ethoxyphenyl group, 5-ethoxyphenyl group, 4-ethoxyphenyl group, 2-methylthiophenyl group, 5-methylthiophenyl group, 4-methylthiophenyl group, 4-methylthiophenyl group, 2-ethylthiophenyl &, 5-ethylthiophenyl group, 4-
Ethylthiophenyl M, 2-trifluoromethylphenyl 15-trifluoromethylphenyl group, 4-17 fluoromethylphenyl group, 2-nitrophenyl 1.5-nitrophenyl group, 4-nitrophenyl M, 5- Fluoro-4-methoxy71nyl group, 2-chloro-5-nitrophenyl group, 4-chloro-2-fluorophenyl group, 5.
4.5-)rimethoxyphenyl group, or 5-chloro-2
-Nitrophenyl group and R (C1""CIO')-
Alkyl groups, such as methyl, ethyl, propyl,
Ethyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, isopropyl group, 2.2
-dimethyl-propyl-1 group, 5,5-dimethyl-butyl-2 group, (C5-c, )-alkenyl group, e.g. 2
-buten-1-yl group, 3-methyl-2-buten-1-
yl group, hexenyl group, hebutynyl group, octenyl group,
(Ca-08)-Alkynyl group, such as propalyl group, butynyl group, pentynyl group, hexynyl group, hexynyl group, octenyl group, phenylalkyl group, such as benzyl group, 2-fluoropenzyl f, 5-fluorobenzyl 14- Fluorobenzyl group, 2-chlorobenzyl group, 6-chlorobenzyl i
, 4-chlorobenzyl 12-bromobenzyl group, 5-bromobenzyl group, 4-bromobenzyl group, 2.4-dichloropenzyl group, 2.6-dichlorobenzyl group, 3.4
-dichlorobenzyl group, 2-methylbenzyl group, 5-methylbenzyl group, 4-methylbenzyl group, 2-nitropencyl M, 3-nitropencyl group, 4-nitropenzyl 1,2-trifluoromethylbenzyl g, 5-t+) fluoromethylbenzyl group, 4-trifluoromethylbenzyl group, 2-methoxybenzyl group, 6-ethoxybenzyl group, 4-methoxybenzyl group, 2-ethoxybenzyl group, 6-nitoxybenzyl group, 4- Etofocypenzol M
, 2-f loboxybenzyl group, 6-f loboxypenzyl group, 4-f loboxypenzyl group, 2-ethoxybenzyl group, 6-butoxybenzyl group, 4-detoxybenzyl group, 2-methylthiobenzyl group, 6-methylthiobenzyl group group, 4-methylthiobenzyl group, 2-ethylthiobenzyl group, 5-ethylthiobenzyl group, 4-ethylthiobenzyl group, 2-butylthiobenzyl group, 6-ethylthiobenzyl group, 4-butylthiobenzyl group For example,

Inorganic and organic acids which form acid addition salts include, for example, t2-hydronic acids, such as hydrochloric acid and hydrobromic acid, as well as phosphoric acid, sulfuric acid, especially nitric acid, monofunctional and difunctional Carboxylic acids and hydroxycarboxylic acids, such as vinegar #I
, maleic acid, succinic acid, fumaric acid, tartaric acid, citric acid, salicylic acid, sorbic acid, milk it, and sulfonic acids, such as p-)luolsulfonic acid and 1°5-7
Talin disulfone WV* can be obtained.

This acid addition salt can be prepared by conventional salt formation methods, such as by adding a compound of formula I to a suitable solvent WC@% and! It can be obtained by adding 1I.

The compounds according to the invention, in particular in the general formula I, in which the group R is a halogen atom, a (01-C4)-alkyl group, a (C1-04)
-alkoxy group, (C~c, )-alkylthio group,
is the same or different phenyl group, which may be substituted one or more times by a trifluoromethyl group or a nitro group, and the group R is an (C~06)-alkyl group, allyl group, propargyl group represents or rhodan atom, (C~c4)-alkyl group, (C1~c,
)-alkoxy M, (C1-C4)-representing the same or different benzyl radicals, which may be substituted one or more times by a furkylthio group, a trifluoromethyl group or a nitro group, have a pronounced fungicidal action. It is.

This (preferably KR is a phenyl group, 2-chlorophenyl group, 5-chlorophenyl group, 4-/lorphenyl group, 2-chlorophenyl group,
．． 4-dichlorophenyl group, 2.6-dichlorophenyl group, 5.4-dichlorophenyl group, 2-fluorophenyl 14-fluorophenyl i4-deromphenyl group.

2-methylphenyl group, 4-methylphenyl group, 4-methoxyphenyl 14-nitrophenyl group, and R1 is a methyl group, ethyl group, propyl group, isopropyl group, pentyl group, hexyl group, allyl group, or Ruyl group, benzyl group, 2-chlorobenzyl group, 4-rependi/I' group, 2.4-f chlorobenzyl t, 5.
Compounds represented by a 4-dichloropenzyl group χ can be mentioned.

The following compounds according to the invention exhibit an outstanding effect: 2-n-butoxy-2-(2-chlorophenyl)-5-
(imidazol-1-yl)-propionitrile, hydrogen nitrate, 2-n-butoxy-2-(2-chlorophenyl)-5-
Cimida-1-yl)-propionitrile, 2-n-butoxy-(4-chlorophenyl)-5-(indazol-1-yl)-! Ropioethryl, hydrogen nitrate, 2-(4-chlorophenyl)-5-(imidazole-1
-yl)-2-n-propoxyzolobionitrile, hydrogen nitrate, 2-(2-chlorophenyl)-5-(imidazole-1
-yl)-2-n-propoxyzolobionitrile.

The compounds of the present invention exhibit particularly fungicidal activity, and at the same time have a remarkable growth-regulating effect on a variety of cultivated plants.

As already mentioned, the compounds of the present 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 inhibitory effect is remarkable in the case of Koshiumatsuso and cotton.

In addition to the above-mentioned actions, the compounds according to the invention also exhibit a killing 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, other plant protection agents or pesticides can be added depending on the desired purpose.

The active substance or mixture thereof can be used - in the form of excavations, e.g. powders, dusters, granules, solutions, emulsions or suspensions, with liquid carriers and/or solid carriers or diluents and optionally It is advantageous to use with the addition of wetting agents, adhesives, emulsifiers and/or dispersing agents.

Suitable liquid carriers are, for example, water, aliphatic and aromatic hydrocarbons, such as penzole, doluol, quidyol, cyclohexanone, isophorone, dimethyl sulfoxide, dimethyl formamide, and also mineral oil fractions and vegetable oils.

Solid carriers include minerals such as clay, silica gel,
Melk, kaolin, attapulgite, coalstone, silicic acid and vegetable products, such as flours, are suitable.

As surfactants, mention may be made of, for example, calcium lignosulfonate, /17 oxyethylene alkyl phenyl ether, naphthalenesulfonic acid and its salts, phenolsulfonic acid and its salts,
Formaldehyde condensates, fatty alcohol sulfates and substituted benzenesulfonic acids and their salts.

If the active substance has to be used for soaking the seeds, dyes can also be incorporated in order to impart a clearly visible color to the soaked seeds.

The content of active substance in the various m-formulations can vary within wide limits. For example, the medicament may contain 10 to 90 kills of active ingredient, about 90 to 101 kills of liquid or solid carrier, and optionally up to 20 kills of surfactant.

The chemical can be applied in a conventional manner, for example, with water as a carrier at a spraying rate of about 100 to 1000 ml/ha. The drug is applied using the so-called low-volume spraying method (Low).
-Volume-Verfahren)"or"low-volume-Verfahren
It is just as possible to apply it in the form of so-called fine granules.

For the preparation of the preparation K, the following ingredients are used, for example: A. Spray pitch a) Active substance 40% clay clay
25 weight silicic acid
20 weight - Cell Pitch (Zellpech)
10 weight b) Active substance 25 weight kaolin 60 weight silica @
C) Active substance
10 weight clay clay 60 weight silicic acid 15 weight Zellpech 10 weight B paste agent 45 weight sodium aluminum silicate 5 weight spindle oil
2 weight - Polyethylene glycol 10 weight Rinsed water
25 parts C0 concentrated emulsion active substance 25% by weight cyclohexane 15% by weight medium dirol 5
The 5% by weight novel compound according to the invention can be prepared, for example, by the general formula: %formula% [wherein R and R1 are as defined above and Y represents a halogen atom or may be halogenated in a side chain] Propionitrile represented by an alkylsulfonyloxy group or an arylsulfonyloxy group is reacted with an imidazole represented by the formula: in the presence of a solvent and optionally a base. Can be done.

As a halogen atom, for example, a chlorine atom, a bromine atom or an iodine atom can be mentioned; as an alkylsulfonyloxy group, a methyl group, a bromine atom or an iodine atom can be mentioned. Suitable are fluoroyl and trifluoromethylsulfonyloxy groups; arylsulfonyloxy groups include, for example, benzylsulfonyloxy and p-dololsulfonyloxy groups.

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

Further, imidazole-alkali gold Rk may be used instead of imidazole.

As solvents are substances which are inert towards the reactants, preferably polar and neutral in nature, such as N.

N-dimethylformamide P%N, N-dimethylacetoand, N-methylbi-tetrapropylene, tetramethylurea, hexamethylphosphate trioxide and benzonitrile are suitable, but high-boiling aromatic hydrocarbons and fats are suitable. Also suitable are truncated hydrocarbons, such as doluol, chlorbenpool or quidylol.

Reaction temperatures can vary within wide ranges. The temperature is 1
Advantageously, it is between 00°C and 200°C. The reaction is
It is carried out under normal pressure or overpressure.

The imidazolyl-propionitrile according to the invention is -1
It is an almost colorless and odorless oil.

Acid addition salts derived from this are colorless and odorless crystalline compounds. This oil is poorly soluble in water, but is more or less soluble in organic solvents such as alcohols, ethers or chlorinated hydrocarbons. Acid addition salts are
It is partially soluble in water and well soluble in polar organic solvents such as acetonitrile, N,N-dimethylformamide, low s alcohols, chloroform and methylene chloride.

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

Example 1 5-(imidazol-1-yl)-2-phenyl-2-
Propoxy-propionitrile, hydrogen nitrate (compound l61) 6-Methylsulfonyloxy-2-phenyl-2-propoxypropionitrile 15m+ (0°055 mol) and imidazole 17.811 ([1,265 mol)] in dimethyl It was kept at 140° C. for 16 hours with exclusion of water and addition of formamide 111j.

The solution is poured onto ice water and extracted twice with 75 m of methylene chloride, the methylene chloride phase is washed twice with water, dried over magnesium sulfate and, after separation with F, concentrated in vacuo with a desiccant. Dissolve the remaining dark oil in Improper Tools,
To this solution is added slightly more than the theoretical amount of 100% nitric acid. Some diethyl ether is added to complete the precipitation. The precipitated product is aspirated and dried.

Yield: 12JI = Theoretical value of 71T Melting point = 168-171℃ (decomposition) Example 2 6-(Imida・Toru 1-yl)-2-7 Enyl 2
-f Roboxypropioethryl (compound A62) 6.2.9 (0,0195 mol) of the hydrogen nitrate of Example 1 is dissolved in methanol and the solution is made basic with dilute ammonia solution under water bath cooling. . After diluting this solution with water,
Extract with ethyl acetate, wash the organic phase with water and then dry over magnesium sulfate. The solution is heated with F and then concentrated in vacuo. An oil remains and is dried in vacuo.

Yield 1t: 4.85N = theoretical value 971 n31 - 1.5260 Similarly, the first compound according to the invention can be prepared.

Compound book title: Nobusan constant 6.2-butoxy-6-(imidazole melting point 2155
-1-yl)-2-phenyl-zolo 157℃ (decomposed) dionitrile, hydrogen nitrate 4.2-det=? C3-(imidazo-)L/nD
39=1.5208-1-yl)-2-phenyl-propionitrile 5.2-allyloxy-6-(imidazo Melting point: 162
--R1-yl)-2-722R 164°C (decomposed) Propionitrile, hydrogen nitrate 6.2-allyloxy-6-(imidazo nD3kl
, 5402-l-1-yl)-2-phenyl-propionitrile Z 2-ethoxy-6-(imidazole Melting point: 182
-1-yl)-2-phenyl-zolo 186℃ (decomposed) bionitrile, hydrogen nitrate 8.2-nitoxy-6-(imida・to-1shi nD44
-1.5247-i-yl)-2-phenyl-propionitrile 93-(imidazol-1-yl) - Melting point: 189-
2-Methoxy-2-7enyl 191℃ (decomposition)
Propionitrile, hydrogen nitrate 10.3-(imidazol-1-yl) Melting point = 57
--2-methoxy 2-phenyl 60℃
-Propionitrile 11.2-(2-chlorophenyl) -Melting point: 162-6
-(imidazol-1-yl) 165°C (decomposition)
-2-Propoxy-propionitrile, hydrogen nitrate 12.2-butoxy-2-(4-chloro Melting point: 178
-tv7xnyl) -3-(imidazo 181℃l
Solution)-1-yl)-propionitrile, hydrogen nitrate 13,2-butoxy-2-(2-chloro Melting point: 1
7furphenyl)-3-(imidazo 178℃(
decomposition)-ru-1-yl)-propionitrile, hydrogen nitrile 14, 2-allyloxy-2-(2-M point: 153-chlorophenyl)-3-(1m at 1155) dabo-ru 1
-yl)-propionitrile, hydrogen nitrate 15.2-(4-chlorophenyl) Melting point: 17
4-13-(imidazol-1-177"O(decomposed)yl)-2-propoxy-probionitrile, hydrogen nitrate 16,2-allyloxy-2-(4 melting point: 152--
Chlorphenyl) -3-155°C (min S) (imidazol-1-yl) -zolobionitrile, hydrogen nitrate 17.2-(2-chlorph x two tv) nD
41=1-5545-3-(imidazol-1-yl)-2-propoxy-probionitrile 18.2-butoxy-2-(4-ri nD41=
1.52880ruphenyl)-3-(iξdab-1-yl)-probionitrile 192-butoxy-2-(2-ri nD41=1
-53290ruphenyl)-3-(Iξda-ru1-yl)-probionitrile 20, 2-7stvO*C2- (2nD41=1
-5490-Chlorphenyl)-imidazol-1-yl)-propionitrile 21, 2-(4-aryalaxnyl) nD4
1=L5337-3-(imidazol-1-yl)-2-propoxy-zolobionitrile 22.2-allyloxy-2-(4nD41=1.54
7-chlorophenyl)-3-imidazol-1-yl)-propionitrile 26,2-benzyloxy-3-1 point: 166-(imidazol-1-yl) 168°C (decomposition) -2-
Phenyl-propionitrile, hydrogen nitrate 24.2-baytyl, t*comb-3-np40=1-5
658 (imidazol-1-yl) tolyl 25.3-(imidazol-1-yl) Melting point: 16
5-l)-2-inpropyloki 168”C(
decomposition) Shiken 2-phenyl-zolobionitrile, hydrogen nitrate 26.3-(imidazol-1-y nD40:1
-5254l)-2-isozolobyloxy-2++ phenyl-propionitrile 27, 2-(4-chlorophenyl) Melting point: 1
52--2-hexyloxy-3-154℃ (decomposition) (
imidazol-1-yl) 1-propionitrile, hydrogen nitrate 28, 2-(4-ri071/)xnyl) n
D40: 1.5197-2-hexyloxy-3- (imidazol-1-yl) 1-propionitrile 292-allyloxy-3-(a Melting point: 1 (decomposed) with Mig1-1-1-yl)- 2-(2-methylphenyl)-deropionitrile, hydrogen nitrate 30.2-(3,4-zochlorophene Melting point: 16
9-nyl)-5-(imidazole 170-0(
decomposition)-1-yl)-2-profoxyprobionitrile, hydrogen nitrate 312-butoxy-2-(2,4 melting point: 148-zochlorophenylene)-3-150"C (decomposition)(imidazole- 1-yl) -propionitrile.Hydrogen nitrate 32.2-allyloxy-2-(2, melting point: 158-4
-dichlorophenyl)-3160'OC min 5)-(imidazol-1-yl)-1propionitrile, hydrogen nitrate 66,2-ditoxy-2-(3,4 melting point: 105-monocyclophenyl)- 3-106°C [%] (imidazol-1-yl)-derobionitrile, hydrogen nitrate 34.2-7 Lylox-3-(inD4o: 1
-5388 midazol-1-yl]-2-(2-methylphenyl)-propionitrile 55.2-(3,4-zoy mouth tv7x nD
4Q: 1-5360yl)-,5-(imidazol-1-yl)-2-profoxyprobionitrile 36.2-allyloxy-2-(3, nD40: 1.5
5004-dichlorophenyl)-3-(imidazol-1-yl)-1propionitrile 37.2-butoxy-2-(2-4-nD40:1-5
381zochlorophenyl)-3-(imidazol-1-yl)-deropionitrile68,2-allyloxy-2-(2,nD40:1-5
5314-dichlorophenyl)-6-(imida-1-yl-1-yl-deropionitrile 392-ethoxy-2(3,4-nD40: 1-53
72zochlorophenyl)-6-(imidazol-1-yl)-propionitrile 40.3-(imidate-1-y) Melting point: 16
8-/L/)-2-yx2tv-2-173-C(min#
)(1,2,2-trimethyl-propoxy)-propionitrile, hydrogen nitrate 41.5-(imidazol-1-y) Melting point: 15
8-ru)-2-(2-methoxy-160'O(decomposed)ethoxy)-2-72-2-propionitrile, hydrogen nitrate 42.2-(2,2-zomethyldero) Melting point: 16
8-boxy)-3-(imidazo-171°C (decomposed)-1-yl)-2-phenyldelobionitrile, hydrogen nitrate 45.2-(2,2-zomethylude Melting point = 89
-Roboxy)-3-(Imida f 91℃-
(1-yl)-2-phenyl-propionitrile 44.2-(2-fluorophenyl) Melting point: 17
0-=3-(imidazole-1-172°C (decomposition film)-2-propoxy-propionitrile, hydrogen nitrate 45.2-butoxy-2-(2-7 melting point: 173-luorphenyl)-3-( A 176°C (min Ps) midazol-1-yl)-propionitrile, hydrogen nitrate 46.2-(4-fluorophenyl) Melting point: 15
0--3-(imidazol-1-152℃(decomposed)yl)-2-propoxy-propionitrile, hydrogen nitrate 47.2-butoxy-2-(4-7 one point: 162-luorphenyl)3-( Imi 165'0 (decomposition) dabur-1-yl)-probionitrile, hydrogen nitrate 48.2-allyloxy-2-(211i* points: 169
--fluorophenyl)-3-171°C (decomposition) (imidazol-1-yl) -deropionitrile, hydrogen nitrate 492-ethoxy-2-(2-7 one point: 172-fluorophenyl)-5-Ci 175-0 (minute Jl!
*) Midazol-1-yl)-propionitrile, hydrogen nitrate 50.2-(2-fluorophenyl) Melting point 217
Fu-6-(imidazol-1-179"O(decomposed)yl)-2-methoxy-probionitrile, hydrogen nitrate 51.3-(imidazol-1-y Melting point: 11
3-l)-2-phenyl-2-116°C (1,2,2-trimethyl-propoxy)-propionitrile 52.5-Cimidazol-1-y nmo':1
．． 5212L)-2-(2-Methoxy-ethoxy)-2-722I rederopionitrile 55.2-(2-Fluorophenyl)n': 1
．． 5145-6-(imidazol-1-yl)-2-propoxy-zolobionitrile 54.2-butoxy-2-(2-)%':
1.5108ruolphenyl)-3-(imidazol-1-yl)-zolobionitrile 55.2-C4-7JL'otv7xs-l)
n, S': 1.51 15-3-(imidazol-1-yl)-2-derobionitrile 56.2-butoxy-2-(4-)nmoO: 1.508
5-Cimidazol-1-yl)-deropionitrile 57, 2-(2-77Lzol7zyl) n
g': 1.5280-6-imidazol-1-yl)-2-methoxy-propionitrile 58.2-nitoxy-2-(2-) n, jO: 1
．． 518 fluorophenyl)-3-(imidazol-1-yl)-norobionitrile 592-allyloxy-2(2-n also O: 1.5258
Fluorophenyl)-6- (imidazol-1-yl) -60,2-allyloxy-2-(4 melting point: 159-1fluorophenyl) -3-161°C (division (imidazol-1-yl) Monozorolioethryl, hydrogen nitrate ring 61, 2-nitoxy-2-(4-) Melting point: 182
-tvotv7xtwotv) -3-(184℃(min*) midazol-1-yl)-degastric bionitrile, 6s@hydrogen salt 62.2-(4-fluorophenyl) Melting point: 19
4--3-(imidazol-1-196°C (decomposed)yl)-2-methoxy-probionitrile, hydrogen nitrate 66.2-nitoxy-2-(4-7 melting point = 54-fluorophenyl)-5- Ci 57°C Ndazol-1-yl)-propionitrile 64.2-(4-fluorophenyl) Melting point 28
8℃-3-(imidazol-1-yl)-2-methoxy-probionitrile 65.2-allyloxy-2-(4!1mo': 1.52
19-fluorophenyl)-3-(imidazol-1-yl)-propionitrile 66.2-decyloxy-3-(i) Melting point: 12
6-ndade-1-yl) -2128°C (decomposed)-pheerudelopioethryl, hydrogen nitrate 67, 2-(3,3-dimethylbuto Melting point: 1
95-xy)-5-C imidazole 198-0(
4)-1-yl)-2-phenyl-propionitrile, hydrogen nitrate ring 68.3-(imidazol-1-yl) 80=1
-5055l)-2-octyloxy-2-phenyl-propionidolyl69, 2-(3,3-dihexide no O:
1.5093Toxy)-3-imidazol-1-yl)-2-phenyl-propionitrile 70.2-(4-bromphenyl) Melting point: 17
1-1-2-butoxy-6-(imi 174°C (decomposed) dabur-1-yl)-probionitrile, hydrogen nitrate 71, 2-(4-bromphenyl) 8 points: 162--6
-(imidazole-1-165℃(decomposition)yl)-2-
Propoxy-probionitrile, hydrogen nitrate 72.2-(4-bromphenyl) Melting point: 15
5-=2-hexyloxy-5-138" CC min> imidazol-1-yl) - Zolobionitrile, hydrogen nitrate 73.3-(imidazol-1-yl) Melting point: 1s
ol)-2-(2-Methylphene 183°C (decomposed))-2-f Roboxyderobionitrile, hydrogen nitrate 74.2-hexyloxy-3-Melting point: 170-(imidazol-1-yl ) 173℃ (decomposition) -2
-(2-methylphenyl)-propionitrile, hydrogen nitrate ring 75.2-(4-bromphenyl)-n♂0:1.54
052-Butoxy-6-(imidazol-1-yl)-propionitrile 76.2-(4-bromphenyl) n60:1,541
8-6-(imidazol-1-yl)-2-propoxy-propionitrile 77.2-(4-deDA)x=ru) nQO:
1-5274-2-hexyloxy-6- (imidazol-1-yl) 1-propionitrile 78.2-butoxy-6-(Shinda no' ”
1.5248Del-1-yl)-2-(2-methylphenyl)-propionitrile 792-Butoxy-6-(imida Melting point: 184
-sol-1-yl) -2-186°C (2-methylphenyl)-propionitrile, hydrogen nitrate 80.2-hexyloxy-3-n80: 1.5163
(imida-to-ru-1-yl) -2-(2-methylphenyl-di-onitrile 81.2-decyloxy-6-(i n80=1
．． 5020midazol-1-yl)-2-1-phenyl-propionitrile82.3-(imidazol-1-yl)-2 n80=1.
5276)-2-(2-methylphenyl)-2-propoxy-zolobionitrile 86.2-Butoxy-2-(3-ri) n80:1.
52820 (ruphenyl)-3-(ilda-1-yl)-probionitrile 84.2-(5-chlorophenyl) Melting point: 16
2-1-2-hexyloxy-5-165°C (min S>(imida-to-l-1-yl)-propionitrile, @ acid hydrogen salt 85.2-decyloxy-3-melting point: 151-(i) 155℃ (decomposition) -2-(
2-Methylphenyl) -Derobionitrihydrogen nitrate 86.3-(Syndade-1-I nD':
1.5173)-2-(2-methylphenyl)-2-octyloxypropionitrile 87.2-decyl/L/oxy-3-(in)-2-(2-methylphenyl)-2-octyloxy1.5139midazol-1-yl -2-(2-methylphenyl)-propionitrile 88.2-butoxy-6-(imida Melting point: 163
-sol-1-yl)-2-167°C (decomposed) (4-methoxyphenyl)-propionitrile, hydrogen nitrate 892-butoxy-3-(imida nD':
1.5228Zol-1-yl)-2-(4-methoxyphenyl)-propionitrile90.2-(4-Chlorphenyl) Melting point: 19
5--2-hexyloxo-3-197°C (decomposition) (imidazol-1-yl) 1-propionitrile, hydrogen nitrate 91.2-(4-chlorophenyl-2-hexyloxy-5-165°C) decomposition) (imidazol-1-yl) 1-propionitrile, which should be used as a proboscis after hydrogen nitrate, Y force t a 17 / renite, + airkylsulfonyloxy group Y table hj general formula 5-end 3-aluminum sulfonyloxy-propioeth 13 A/l
Some of the 1-alkyl-resulfonyloxy compounds are known or can be prepared using methods known per se (for example, Rubi
n et al., @JAC8'', Volume 67, 111921 [hereinafter,
1945; H@l! 8 others, ”Ber, dt,
Chew, o@, #, 1lI vol. 50, p. 394, 1917). The phenylacetonitrile shown is itself hydroxymethylated by a well-known method, and the resulting general formula is -R Z -C-CH, -OH.N [where 2 and R are the same as above]. 3 indicated by
-Hroxyzolobionitrile, obtained by reaction with a monovalent sulfonic acid salt conductor, such as sulfonic acid chloride, optionally under axJ of an acid hydroxide. Hitherto, hydroxymethyl compounds of the general formula (2) are not known in the literature.

General formula 1, in which Y represents 1 halogen atom, known from publications
No-3-no-rodenederobionitrile can be obtained by reacting the above-mentioned phenylacetonitrile Y and zohalogenmethane in general formula amounts by a method known per se.

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

2-phenyl-2-propoxy-acetonitrile 27
g (0,154 mol) of Ypyricine was dissolved in 120 dK#, and to this solution was added 18.5 g of paraformaldehyde (0.5 g).
6 14 mol) is added. Tetrazotylammonium hydroxide (TBAOH) was added to this suspension under ice cooling.
) 7.71117 Y and stir vigorously for 17 hours. The reaction mixture was poured into ice water and extracted twice with ether. The ether phase is then washed 12 times with an aqueous sodium chloride solution and dried over magnesium sulfate. After removing the desiccant t'F and under vacuum, a colorless oil remained. You can do more work without changing the horse.

Collection: 2 B. 4 g=90 6-hydroxy-2-phenyl-2-propoxy-zolobionitrile 3-hydroxy-2-phenyl-2-7'roboxyderopionitrile 28, F (0.1 3 6
methanesulfonic acid chloride 1 9.5 Ii (0.17
1 mole) χ′If & add. At 10°C, 18.6 g (0.184 mol) of triethylamine is added.

The solution was further stirred for 30 minutes at temperature Y'', and the precipitated triethylaznohydrochloride was filtered and subjected to S-raying.The residue was taken up in ether, washed with dilute HCl solution, and washed with water. , with sodium bicarbonate solution and again twice with water.

The solution is dried over magnesium sulfate, filtered with suction from the desiccant Y, and concentrated. This oily residue #! Dry in vacuum. This oily residue can be removed using thin film chromatography KJ.
: It turns out to be pure. Yield: 3 2.2 7 g = 86% of the fI11 value
D = 1.5 0 0 0 3-Methylsulfonyl-2-phenyl-2-propoxy-probionitrile The following examples were carried out in the form of the sllll agent described above.
How to use the monster according to the invention: It is used in various ways.

Example 6 Barley Helm/Tosborium speck
Effect of seed treatments on Inthosporium spec- ).

Helminthosborium gramineum (Helmi)
Seeds of barley naturally diseased by nthosporium gramin@um) were untreated or treated as described in the table, neutralized in pots with ±IIt and germinated at temperatures below +16°C. After germination, the sprouts were irradiated with artificial light for 12 hours every day. Approximately 5
After a week, all the plants had germinated and one diseased plant was counted in each test group.

The killing effect is calculated using the following formula, which is 2
Exists as a spray powder of 0%.

15095.6 2 50 100 3 50 100 4 50 100 5 50 100 6 50 100 7 50 100 8 50 100 9 50 100 10 50 10011
50 10012 50
10013 50 10014
50100 15 50 10016
50 10017
50 10018
50 10019
50 10020
50 1002150100 Comparative chestnut agent example 4 Erysi of Cucurbitaceae plant in greenhouse
Effect of prophylactic treatment on Erysiphe cichoracearum Young seedlings of Cucurbitaceae plants sprayed until dripping with the above-mentioned active substance concentrations
The seeds were inoculated by spraying dried downy mildew gaules of A. arum) and kept at a constant temperature of 24° C. in a -IIK greenhouse together with the inoculated control seeds. After one week, the downy mildew area affected was evaluated by the total foliage area and the tK fraction. The herbicidal effect was calculated as follows:
% spray S powder.

5 0.025 1000.001
100 0, [)01 -87 U, LIUO2100 0,001100 0,0002100 0,000298 U・0002 100 0.0002 100 o, ooi io.

O,0002100 0,001100 0,0002100 0,0002100 0,0002100 0.00005 100 Example 5 Pyricularia oridex (Pi
ricularia oryzae) Effect of leaves on K.

Rice seedlings were sprayed until dripping with the active substance concentration listed in the table. After drying, treated plants and untreated control plants were sprayed with the leaf spot pathogen (Blatt).
fleckenerreger) Piricularia oryzae (approximately 200,000/day), were inoculated by spraying, moistened and kept at a temperature of +25°C to +27"C in a greenhouse.

After 5 days, it was determined how much of the stem and leaf area was affected by the disease. From this morbidity, the fungicidal action was calculated as follows: The morbidity of the substance was 20 gIf) formulated as a spray powder.
2 νυ Example 6 Botrytis cinerea on tomatoes in a greenhouse
tis cinerea) Effect of prophylactic leaf treatment on K.

Tomato seedlings were sprayed until dripping with the active substance concentrations listed in the table. After the spray coating has dried, treated and untreated plants are inoculated by spraying with a suspension of spores (approximately 1000 spores/1117 of juice solution) of the botrytis pathogen Botrytis cinerea and moistened. The temperature was then maintained at approximately 20°C in a greenhouse.

After the untreated plants (= morbidity rate 100) collapsed, the morbidity χ of the treated plants was determined. The sedicidal action was calculated as follows: The compound according to the invention was present as a 2o formulation. 2 0.025 953
0.025 8012
0.025 9013 0
．． 025 9514 0.0
25 6015 0.025
8516 0.025
70170・025 90 18 0.025 9019
0.025 9520
0.025 9021
0.025 80n Example 7 Grape Zorasumopak bitekola (Plas
Effect of pre-spinning medicine on mopar'a viticola).

Write down the data with approximately 5 to 8 's'lf's.
After the spray film has dried, spray under the leaves with 1 liter of an aqueous suspension of sporangia (approx. The temperature was kept constant at ℃ in an atmosphere as saturated with water vapor as possible.

Air humidity on the second day? Return to normal height for 3-4 days (30-70% saturation) and then hold at steam saturation for 1 day. Continuing, the whisper of the area affected by true*a from each leaf @seχ
The average fungicidal activity per treatment was calculated as follows: The material was formulated as a 20% spray powder.

11 0.025 8912
0.025 95.513
0.025 92.514 0.
025 7315 0.025
95.416 0-025 8
217 0.025 92.718
0.025 94.619
0.025 95.5200・025
65 21 0.025 81 Cases 8 In the laboratory, Prunus japonicus Y was treated with an aqueous emulsion of the drug according to the invention.

The concentration of active substance in the emulsion was iooppm.
Active substance emulsion? [A glass slide was placed for this purpose in a 200 d glass tube with 10 d't'. KFJ1tYI on this slide glass! Seta, this P paper?
Impregnated with the solution and then put 10 seeds of Phyllanthus on top
Then, the cells were uniformly distributed (0) onto this tube in a Petri dish.
'For each substance, two glass tubes were prepared.

For evaluation (1 leaf and root lengths were measured 7 days after germination).

In the table, the shifts associated with the control are listed and expressed as a percentage.

The compounds according to the invention are suitable for roots and 1
It has been found that it exerts a remarkable effect on leaf growth. This is evident in the demand rate (>100%) or rejection rate (<1001s) of the individual parts.

Compound according to the invention Growth rate 1
71 57 2 86 71 3 67 100 4 67 57 5 67 43 6 67 71 7 85 86 8 67 71 9 67 71 10 83 7111
100 6712 50
2213 50 2214
100 7815
67 4416 50
4417 85 5618
67 6719
100 5620 83
7821 50
4422 50 57 Example 9 Cotton at the embryo collection stage (K. imblatta-
tadium) 11.

The chemical agent according to the present invention is 1/ha and 2/
The total length of the plants and the length of the IN1 internodes were measured after 3 applications by spraying the plants at the usage of 0 ha. In the table, the results are stated in the form of percentage values compared to the control. ing.

In general, the reduction in growth Y is more significant than that of the comparative specimens.

11 1 75 32469 12 1 83 602 5
9 19 Comparative drug example 10 Grain downy mildew disease picture of barley Erysihue gras varnish (l1
Effect of seed temperature sensitivity on summer barley seeds Y not temperature sensitive or active substance 100 g
/l 00#, sown in soil w and germinated in a greenhouse at a temperature of about 20°C. After the formation of 811 leaves, the plants were inoculated by rubbing against plants infected with downy mildew. After one treatment, the area of shoots and leaves covered by downy mildew sIK was calculated as follows. evaluated. This evaluation was carried out according to the following criteria: 0 = total elimination 1 = 90 fights eliminated 2 = 80 - eliminated 6 = 70% eliminated 4 = 60% eliminated 5 = 501 eliminated 6 = 40 fights eliminated 7 = 60+ eradications 8 = 20% eradication 9 = 10 fights eradicated 10 = no damage Compounds according to the invention have an active substance content of 20% 4
It exists as an IL content.

Unlike the comparative drugs, the compounds according to the invention
), it was also shown to be completely compatible with P. elegans.

1 100 10 2 100 10 5 100 10 6 100 10 7 100 108
100 109
99.5 1010
100 1[;)11
93 1015
100 1016 9
9 1017 95
1021 100
1022 100
10 Comparison Tablet Example 11 Brown spot disease of sugar beet (Beta vulgaris) (C5rcospora
beticola)) against -jb prophylactic leaf collection treatment action.

It has 4 leaves that have grown on each leaf! Radish Y was sprayed at the indicated concentration until it dripped. 4<# After the wall membrane has dried, the plants that have increased by 6 and the untreated control plants Cercospora - Cercospora 1500 (
Ha/df) [11111+[Te uniform injection 11j.

Plant'lk: Maintained constant temperature in a greenhouse for 4 days at 26°C and water vapor saturation of 9 atmospheres, and then further heated in a greenhouse at about 22°C [10
After 0 days of storage, the diseased stem and leaf area was recorded as Y. The insecticidal action was then calculated as follows: π: 0.01 96 Growth inhibition.

Nutrient solution 20jE/Y consisting of degetsu juice and water (1:1)
into a flask with a content of 100 d, to which the powdered active substance glI preparation χ was added.
igitatum) conidia (spores). 2
After a treatment time of 5 days at 2-24°C, the fungal infestation area on the nutrient solution surface was evaluated.

Rating 20 = No fungal growth i = Individual root cause colonies on surface a 2 = 5-10% of the surface area is covered by fungal infestation areas 3 = 10-30% of the surface area is covered by fungal infestation areas 4 = 30-60% of the surface area is covered by the fungi-infested area 5 = 60-100 tIk of the surface area is covered by the fungi-infested area Active substance, active substance of the nutrient solution 4!11 degrees and results teeth,
They are listed in the table below.

o, ooi excellent 0 0, υU1 s υ 5B 0.0O05*
00.001 Vomit 0 Comparative drug (according to West German Patent Publication No. 2604047) Control
5 Case 16 Uncinula nacatl (Uncin)
Effect of prophylactic foliage treatment on ula nacator).

Item 4 sill panel (811va) with about 8-10 leaves
Nor. After drying, spray the plant with a straight layer of Uncihula neca.
tor) conidia by a dry method and heated at approximately 22°C for 12
The temperature was maintained in a greenhouse for several days. Next, the morbidity was evaluated as a percentage of T-grave 1 product and Y percentage, and the morbidity was calculated as follows: The morbidity rate was calculated as follows: The 3SK Slow 1 formulation was present as a 20% spray powder. You can know the evaluation from the table.

2 93 85 5 100 1004
100 1005 100
1006 100 997
100 898
100 959 8
7 6310 10
0 4911 10
0 10012 10
0 6313 100
9514 66
4315 100
10016 99
8917 100
10018 86
8019 100
8920 93
8621 10
0 10022 1
00 92 Case 14 In the open field, the fungus Benzilia inaequarix (
Effect of prophylactic foliar treatments on Venturia inaqualig).

Young shoots of Linde of variety MM 106 were treated once with 0.1 of the active ingredient until they dripped.

After the spray coating has dried, conidia C55000D+@/y
Spray the suspension of d) on the stems and leaves, and then spray the young shoots. After putting a polyethylene bag on it, I infected it with a true tooth under the shade for 3 days. removed. After a total test time of 2M weeks, the percentage of area affected by inflammation was evaluated. Untreated vs 'R has 99% morbidity'5
sY indicated. The results of the treatment were calculated as follows: The compound was present as a 20 g atomized powder.

18 100 985 Example 15 Apple inflammation in the open field - Benzulia inaequalis (V
Effect of oil dynamic foliage treatment on cultivar MM 106 (Enturia 1naqualis) K. By spraying with a suspension of young shoot chi conidia (330,000 pieces/R1) in the growing state of cultivar MM 106 and immediately covering with a polyethylene bag. kept moist. Plants were placed under semi-shade. After 6 minutes, I removed this loan. Seven days after inoculation, the plants were treated with an active substance concentration of 81% YO until dripping. Furthermore, 1
``After a week, the percentage of the area of one leaf affected by apple inflammation was evaluated as 99% in the untreated case. The effect of the treatment was calculated as follows: 2
9618 100
19 100 Comparative Drug Example 16 Barley Erysiphe graminis
graminig).

Barley Y at the first foliar stage was applied in the dropwise wet method with the addition of alkaryl polyglycol ether as a wetting agent (0.05%) at the stated active substance concentrations. After the spray coating had dried, the plants and untreated control plants were uniformly rubbed with downy mildew-infected grains and then kept at 20-22°C in a greenhouse for one week. Subsequently, the average downy mildew morbidity rate was recorded for each pot (18 to 20 plants). The fungicidal action was calculated using the following formula KJ: The substance according to the invention was present as a 20% formulation.

3100100 4 100 1005
100 1006
100 1007
100 1008 10
0 1009 100
10010 92
9011 100 10
012 100 1001
3 100 10014
100 100 (99) 15100100 16 100
10017 100
10018 100
10019 10
0 10020
100 10021
100 10022
100 100 cases 1
7 Uromyces apenzoku 2tus in the greenhouse
ces appfndiculatus) (wMetal rust disease [) Effect of preventive foliage @ field.

Inden bean t100 p in half-grown primary foliage stage
The concentration of active substances in pm drops! It was sprayed with. After the spray coating had dried, the treated plants and the rice-treated control plants were treated with Uromyces apenjicus 2tus.
It was sprayed with a suspension of summer spores of A. appendiculatus). Next, this plant was kept at a constant temperature of 22°C for 2 days in a humid room, and then kept at about 22°C under a greenhouse. Eleven days after spraying with spores, the number of spores was counted (an average of 253 spores per leaf of the rice-treated control).
.

The fungicidal action was calculated as follows.The substance according to the invention is present as a 20% formulation and exhibits a fungicidal action of over 90'jY91 96 95 94 12 100 15 99.5 695 17 ．． 99-4 18 99.9 998 21 98.6295 795 897 Example 18 Helminthoborium teres
sporium tires) (= e-lenohora・
Teres (Pyrenophora ters5)),
Effect of prophylactic single-leaf treatment on inflammation of P. occidentalis.

Barley seedlings at the first leaf stage were sprayed until dripping at the concentrations listed, and after the spray film had dried, the plants and the rice-treated control plants, Helminth teres (HelminthO- sporium tsre
Spray with a suspension of conidia in a humid π chamber for 20~
Cultured at 22'0 for 2 days.

One week after inoculation, the morbidity Y percentage of the industrial area was recorded. The fungicidal activity was calculated as follows: The fungicide was present as a 20% formulation.

Compound according to the present invention Sesshinkoi effect 35
90 9066
95 9037 95
9038 95 9039
95 9540
100 10041 100
9842 100 1004
3 100 10044
100 10046 1
00 10047 100
10048 100 8949
100 100
50 100 96
51 100 1
0052 98
8953 100
10054 96
9655 100
10057 10
0 10058
100 9659
100 89 Example 19 Infection of barley rotting fungus Puccinia hordei in a plant growth room with controlled temperature and humidity.
Effect of preventive irises treatment on barley seedlings at the first foliage stage. After spraying mv dry, treated plants and non-46 Ru-
A control plant was inoculated with a plant Y infected with small rot and placed in a plant growth chamber. The seeds were incubated for 10 days at 15° C. in mostly moisture-saturated air for the first two days. Thereafter, the distribution of leaf area affected by rust was recorded as a percentage. Fungicidal activity was calculated as follows: Compounds were present as a 20 hour formulation. The table demonstrates the good to very good effect of a number of the compounds according to the invention.

52 100 42 100 3100 45 100 6100 47 100 48 100 49 100 54 10055
10058
10061
10064 10065
10066
10067
1 o.

69 10071
10072
10074 10
075 10076
10077
10078 1
0079 10080
100 cases 20 ma degree barley tribute 1 [Pucclnis striformis]
Effect of prophylactic foliage treatments on Triiformis triiformis).

Barley IMyt was sprayed at the 1 stem and leaf stage at the stated concentration until dripping. After the spray coating has dried, treated plants and untreated seeds are treated with Puccinia striiforis in 1.1.2-trifluoro-1,2,2-trichloroethane.
Mis ) was sprayed with a suspension of summer spores and kept at a constant temperature of 150'O in a plant growth chamber. Reached IIl. After 15 days, the plants were inseminated with Y percentage of the area of stems and leaves affected by mildew.

The fungicidal activity of the two compounds according to the present invention was calculated as follows:
0pp 33ppm llppm5
100 - -12
100 100 10014
100 - -15
100 100 10016
100 - -
17 100 100 10
018 100 100
9528 100 98
78 Case 21 Growth of barley Helminthoborium satideum (H@1mintho-spor) in a temperature-humidity controlled plant growth room
Effect of seed treatments on S. ium sativum).

Helminthoborium ψsachidem (Helmintho)
The active substance of the drug according to the invention was sprayed with 50.9/100 V of the active substance of the drug according to the invention on barley seeds artificially infested with S. -sporium sativum). Test group and treated or untreated seeds 'It6.5X6.5
'Seed in my plastic body. Sand was used as soil. Each test group was repeated twice. This pot Y was placed in a plant growth chamber at 15°C.

After 4 weeks, from the average of 6 replicates tested on the morbidity as a percentage of the germinated plant Y stems, the fungicidal action was calculated as follows. It existed as a prescription.

99 799 21 99-525
100 26 100 2c) 100 32 100 3B 100 Comparative Drug Table Example 22 In vitro fatty inflammation of beans (Fsttflecken
-krankheit) pathogen Pseudomonas 7
Pseudomonas phaseo
licola).

Raw malt agar Y was cooled to about 45° C. after thermal esterification, then the test substance was mixed in an aqueous preparation and poured into a plastic Petri dish. After solidification of the culture medium, plates with treated agar and untreated agar as a control were incubated with the fatty inflammatory pathogen Pseudomonas phaseolicola (Pse).
The seeds were inoculated in the center of the inoculation ring with a suspension of A. udomonasphaaeolicola). Next, the dish was kept at a constant temperature of 22° C. After 2M weeks, the expansion of the radius of the colony was measured as the microdonts grew. From the average of two replicates per test group, the bacterial inhibition was calculated as follows: The compound was present as 20% formulation.

Pseudomonas 7aceolycola
Inhibitory effect of 250 ppm of active substance in agar against P. asphaseolicola).

71 71 167 286 378 575 767 875 971 21 71Example 26 Effect of preventive industrial treatment against the downy mildew Erysiphe graminis K of barley in a greenhouse.

Barley at the first grave leaf stage was dripped once and sprayed until b. After the spray coating has dried, dry downy mildew can be removed by rubbing the infected seeds on treated plants, untreated control plants, and test plants. inoculated with IfR offspring. Thereafter, the test plants were placed in a greenhouse at approximately 20-22°C.
The plants were kept at a constant temperature, and one week later, the morbidity rate χ percentage of the stem and leaf area was evaluated. The fungicidal activity was calculated as follows: The compound was present as a 20% formulation - The compound according to the invention Fungicidal activity dominant 1100
pp 20ppm28 100
10029 100 10030
100 9951
100 10032 -
10033 100 10034
100 10035
100 10036 100
10057 100 10058
100 10039
98 9040 100
9141 100 10042
100 10039691 44 100 10
045 100 9
646 100 1
0047 100
10048 100
10049 100
10050 100
10051 100
10052 100
10055 100
10054 100
10055 100
10056 100
10057 100
10058 100
8759 100
10060 100
9861 100
10062 100
10063100100

Claims (1)

[Claims] 1. General formula! = [In the formula, R is a halogen atom, (C□-C4)-alkyl group, (C
1-C4)-alkoxy group, (C, ~C,)-alkylthio group, trifluoromethyl group or nitro group
represents the same or different aromatic hydrocarbon bulk radicals which are substituted one or more times. R1 is (C1-CIO)-alkyl group, (c3-cs)
-Represents a fulkenyl &, (C3-c8)-alkynyl group or a halogen atom, (00-04)-alkyl group, (C-04)-alkoxy group, (C1-C4)-
the same or different phenylalkyl groups which may be substituted one or more times by an alkylthio group, a trifluoromethyl group or a nitro group] and their combinations with inorganic and organic acids. Acid addition salts. 2, R is a halogen atom, (01-C4)-alkyl group, (C1-C4)-alkoxy group, (C1-C,)-
represents the same or different phenyl group, which may be substituted one or more times by an alkylthio group, a trifluoromethyl group or a nitro group, and R1 represents a (C1-c, )-alkyl group, allyl group, or propalkyl group; or halogen atom, (C1-c4
)-alkyl group, (C1-C,)-alkoxy group, c0
1-04) - 4Irl representing the same or different benzyl radicals, optionally substituted one or more times by an alkylthio group, a trifluoromethyl group or a nitro group
f. Imidazolyl-propionitrile according to claim 1. 5. The compound according to claim 1, which is 5-(imidazol-1-yl)-2-7enyl-2-f lopoxypropionitrile, hydrogen nitrate. 4.5-Cimidazol-1-yl)-2-phenyl-
The compound according to claim 1, which is 2-7'lopoxyp p-bionitrile. 5.2-Ethoxy-5-(imidazol-1-yl)-
The compound according to claim 1, which is 2-phenyl-propionitrile, hydrogen nitrate. 6.2-Ethoxy-6-(imidazol-1-yl)-
A compound according to claim 1 which is 2-phenyl-propionitrile. The compound according to claim 1, which is Z 2-allyloxy-6-(imidazol-1-yl)-2-phenyl-propionitrile, hydrogen nitrate. 8.2-Allyloxy-6-(imidazol-1-yl)-2-phenyl-zolobionitrile! The compound described in section s1. 92-Ethoxy-6-(imidazol-1-yl)-2
-Phenyl-zolobionitrile, hydrogen nitrate, %
A compound according to claim 1. 10.2-Nitoxy-6-(imidacyl-1-yl)
82. The compound of claim 81 which is -2-phenyl-zolobionitrile. 11. The compound according to claim 1, which is 5-(imidazol-1-yl)-2-methoxy-2-phenyl-propionitrile, hydrogen nitrate. 121-(i,mida-t-1-yl)-2-methoxy-2-phenyl-propionitrile. 41. The compound according to claim 1. 15.2-(2-chlorophenyl)-5-(imida r-
(1-yl)-2-propodipropionitrile,
The compound according to claim 1, which is a hydrogen nitrate salt. 14.2-ethoxy-2-(4-chlorophenyl)-6
-(imidazol-1-yl)-7″ropionitrile,
The compound according to claim 1, which is a hydrogen nitrate salt. 15.2-ethoxy-2-(2-chlorophenyl)-5
-(imidazol-1-yl)-zolobionitrile, hydrogen nitrate, the compound according to claim 1. 16.2-allyloxy-2-(2-chloro7enyl)
The compound according to claim 1J1, which is -ri-(imidazol-1-yl)-zolobionitrile, hydrogen nitrate. 17. 2-(4-Chlorphenyl)-5-(imidazol-1-yl)-2-zorobo! Robionitrile,
The compound according to claim 1, which is a hydrogen nitrate salt. 18.2-allyloxy-2-(4-chlorophenyl)
-5-Cyl-1-yl)-propionitrile, hydrogen nitrate. 19. The compound of claim 1 which is dipropionitrile in 2-(2-chlorophenyl>-5-Cimidazol-1-yl)-2-propo. 20.2-Cytoxy-2-(4-chlorophenyl)-3
-(imidazol-1-yl)-zolobionitrile, according to claim IiB. 2t 2-ethoxy-2-(2-chlorophenyl)-3
The compound according to claim #11, which is -(imidazol-1-yl)-propionitrile. 22.2-7lyloxy-2-(2-chlorophenyl)
2. The compound according to claim 1, which is -imida-ru-1-yl)-zolobionitrile. 23.2-(4-,chlorphenyl)-5-(imidazol-1-yl)-2-propoxy-zolobionitrile. 4+1 The compound according to claim 1 of am. 24.2-allyloxy-2-(4-chlorophenyl)
2. The compound according to claim 1, which is -6-imidazol-1-yl)-propionitrile. 25, 2-benzyloxy-6-(iodade-1-
2-phenyl-zolobionitrile, hydrogen nitrate. 26.2-benzyloxy-5-(iotasol-1-
2. A compound according to claim 1, which is 1l)-2-phenyl-propionitrile. 27. The compound according to claim 1, which is 5-Cimidazol-1-yl)-2-isopropyloxy-2-phenyl-propionitrile hydrogen nitrile. 28.5-(imidazol-1-yl)-2-isozolobyloxy-2-phenyl-zolobionitrile,
% of the compound according to claim 1. 29. Claim # which is 2-(4-chlorophenyl)-2-hexyloxy-6-(imidazol-1-yl)-probionitrile, hydrogen nitrate! Compound according to item 1. 50. The compound according to claim 1, which is 2-C4-chlorophenyl)-2-pequinyloxy-6-(imidazol-1-yl)-propionitrile. 5t 2-allyloxy-6-(imimeψ-l-1-yl)-2-(2-methylphenyl)-propionitrile, hydrogen nitrate, 1% of the compound according to claim 1. 52. The compound according to claim 1, which is 2-<5.4-dichlorophenyl)-3-(imidazol-1-yl)-2-propoxy-propionitrile, hydrogen nitrate. 66.2-butoxy-2-(2,4-dichlorof
2. The compound according to claim 1, which is hydrogen nitrate of -5-(imidazol-1-yl)-propionitrile. 34. The compound according to claim 1, which is 2-allyloxy-2-(2,4-dichlorophenyl)-3-(imidazol-1-yl)-7'0 bionitrile, hydrogen nitrate. 55.2-Ethoxy-2-(5,4-dichlorophenyl)-1-(imidazol-1-yl)-7°tetrabionitrile, hydrogen nitrate. 4I Claims #! Compound according to item 1. 66. The compound according to claim 1, which is 2-allyloxy-5-(imidazol-1-yl)-2-(2-methylphenyl)-zolobionitrile. 57. The compound of claim 1 which is 2-C5,4-dichlorophenyl)-6-(imidazol-1-yl)-2-f roboxyzolobionitrile. 58. The compound of claim 1 which is 2-7lyloxy-2-C5,4-dichlorophenyl)i-(imidazol-1-yl)-zolobionitrile. 692-butoxy-2-(2,4-dichloro7enyl)
The compound according to claim 1, which is -5-(imidazol-1-yl)-progionitrile. 40. The compound according to claim #!1, which is 2-allyloxy-2-(2,4-dichlorophenyl)-3-(imidazole-1-(l)-zolobionitrile. 4t 2-di The compound according to claim 1, which is toxy-2-<5.4-dichloro7enyl)-5-(imidazol-1-iA/)-propionitrile. 42,5-(imidazol-1-yl)-2-phenyl-2-(1,2,2-)limethyl-zotepoxy)-zolobionitrile, hydrogen nitrate, according to claim 1. Compound. 43,5-(imidazol-1-yl)-2-(2-
The compound according to claim 1, which is (methoxy-ethoxy)-2-phenyl-zolobionitrile, hydrogen nitrate. 44. 2-(2,2-dimethylpropoxy)-6-(imida-do-''cyl--yl)-2-phenyl-propionitrile, hydrogen nitrate, claims 1N1
The compound described in m. 45. The compound according to claim 1, which is 2-(2,2-dimethylpropoxy)-6-(imidazol-1-yl)-2-phenyl-propionitrile. 46. The compound according to claim 1, which is 2-(2-fluorophenyl)-5-(imidazol-1-yl)-2-propoxy-zolobionitrile, hydrogen nitrate. 47.2-F)xy-2-(2-fluorophenyl)-
5-(imidazol-1-yl)-propionitrile,
112. The compound of claim 111, which is a hydrogen nitrate salt. 48. Claim I which is 2-(4-fluorophenyl)-3-(imidazol-1-yl)-2-propoxy-propionitrile, hydrogen nitrate! Compound according to item 1. 492-butoxy-2-(4-fluorophenyl)-5
-(imidazol-1-yl)-zolobionitrile, hydrogen nitrate, the compound according to claim 1. 50. The compound according to claim 1, which is 2-allyloxy-2-(2-fluorophenyl)-3-(imida-to-ru-1-yl)-zolobionitrile, hydrogen nitrate. 51.2-Ethoxy-2-(2-fluoro7enyl)-
5-(imidazol-1-yl)-onitrile,
The compound according to claim 1, which is a hydrogen nitrate salt. 52.2-(2-fluorophenyl)-5-(imidazol-1-yl)-2-methoxy-zolobionitrile,
The compound according to claim 1, which is a hydrogen nitrate salt. 5t,3-(imidazol-1-yl)-2-7'dinyl-2-(1,2,2-trimethyl-propoxy)-norobionitrile. 54, 3-(imidazol-1-yl)-2-(2
-methoxy-ethoxy)-2-7enylpropionitrile. 55. The compound according to claim 1, which is scisolobionitrile in 2-(2-fluorophenyl→, -5-(imidate-1-yl)-2-prophos). 56.2-Butoxy -2-(2-fluorophenyl)-
A compound according to claim 1 which is 3-(imidazol-1-yl)-propionitrile. 57.2-(4-fluorophenyl)-3-(Iξri・
%ff1fl! A compound according to item 1 of the claimed scope. 58.2-Butoxy-2-(4-fluorophenyl)-
A compound according to claim 1 which is 5-(imidazol-1-yl)-propionitrile. 59. The compound of claim 1111 which is 2-(2-fluorophenyl)-6-imidazol-1-yl)-2-methoxy-propionitrile. 60.2-ethoxy-2-(2-fluorophenyl)-
1% Compound of claim 1 which is 5-(imidazol-1-yl)-zolobionitrile. 612-allyloxy-2-(2-fluorophenyl>
The compound according to claim 1, which is -5-<imidazol-1-yl)-propionitrile. 62. The compound according to claim 1, which is 2-allyloxy-2-(4-fluorophenyl)-5-(imidazol-1-yl)-zolobionitrile, hydrogen nitrate. 63.2-Ethoxy-2-(4-fluoro7enyl)-
3-(imidazol-1-yl)-zolobionitrile,
The compound according to claim #11, which is a hydrogen nitrate salt. 64. The compound according to claim 1, which is 2-C4-fluorophenyl)-3-(imidazol-1-yl)-2-methoxypropionitol, hydrogen nitrate. 65.2-ethoxy-2-(4-fluorophenyl)-
A compound according to claim 1 which is 5-(imidazol-1-yl)-propionitrile. 66. A compound according to claim 1 which is 2-(4-fluorophenyl)i-(imidazol-1-yl)-2-methoxy-propionitrile. 67. The compound according to claim 1, which is 2-allyloxy-2-(4-fluor-7enyl)-1-(imida-to-ru-1-yl)-zolobionitrile. 68. The compound according to claim 1, which is 2-decyloxy-6-(imidazol-1-yl)-2-phenyl-propionitrile, hydrogen nitrate. 69. The compound according to claim 1, which is 2-(5,5-dimethylbutoxy)-5-(imida-to-1-yl)-2-phenyl-propionitrile, hydrogen nitrate. . 70. The compound according to claim 1, which is 5-(imidazol-1-yl)-2-octyloxy-2-phenyl-zolobionitrile. 71. The compound according to claim 1, which is 2-1.3-dimethoxybutoxy)-5-imidazol-1-yl)-2-phenyl-propionitrile. 72. 2-(4-Bromphenyl)-2-butotoshi 6
-(imida-ru-1-yl)-propionitrile,
The compound according to claim 1, which is a hydrogen nitrate. 73.2-(4-bromphenyl>-5-Cimidazol-1-yl)-2-f lopoxy! ropionitrile,
The compound according to claim 1, which is a hydrogen nitrate salt. 74.2-(4-bromphenyl)-2-hexylo+
The compound according to claim 1, which is hydrogen nitrate of '/-5-imitater-1-yl)-propionitrile. 75. The compound according to claim wL1, which is 5-C imidazol-1-yl)-2-(2-methylphenyl)-2-7'roboxyprobionitrile, hydrogen nitrate. The compound according to claim 1, which is 762-hexyloxy-6-(imidazol-1-yl)-2-(2-methylphenyl)-propionitrile, hydrogen nitrate. 77.2-(4-bromphenyl)-2-butoxy-5
112. The compound of claim 111, which is -(imidazol-1-yl)-propionitrile. 78.2-(4-bromphenyl)-3-(ikidashi-
2. The compound according to claim 1, which is (1-yl)-2-propoxy-propionitrile. 79.2-(4-bromphenyl)-2-hexyloxy-5-(imidazol-1-yl)-zolobionitrile. A compound according to claim 1. 80. The compound according to claim 1, which is 2-butoxy-5-(imida-1-1-yl)-2-(2-methylphenyl)-propionitrile. 81,2-butoxy-ro-(imidazol-1-yl)
The compound according to claim 1, which is -2-(2-methylphenyl)-zolobionitrile, hydrogen nitrate. 82.2-hexyloxy-5-(imidazole-1-
2-(2-methylphenyl)-progionitrile. 83. The compound according to claim 1, wherein 2-decyloxy-5-(imidazol-1-yl>-2-phenyl-propionitrile). 84.5-(imidazol-1-yl)- The compound according to claim 1, which is 2-(2-methylphenyl)-2-f roboxyzolobionitrile. 85.2-Butoxy-2-(5-chlorophenyl)-5
4H4F compound according to claim 1, which is -(imidazol-1-yl)-zolobionitrile. 86.2-C5-ri-tetralphenyl)-2-hexyloxy-5-(imidazol-1-yl)-propionitrile, hydrogen nitrate, special! F! F. A compound according to claim 1. 8″l 2-decyloxy-6-(imidazole-1-
The compound according to claim 1, which is hydrogen nitrile)-2-(2-methylphenyl)-propionitrile. 88,5-(imidazol-1-yl)-2-(2-
2. The compound according to claim 1, which is (methylphenyl)-2-octyloxy-norovionitrile. 89.2-1"Syloxy-5-(imidasoru 1
2-(2-methylphenyl)-propionitrile. 90.2-Butoxy-5-(imidazol-1-yl)
-2-(4-methoxyphenyl)-zolobionitrile,
The compound according to claim 1, which is a hydrogen nitrate salt. 91.2-Butoxy-6-(imidazol-1-yl)
-2-(4-methoxyphenyl)-zolobionitrile, Claim F! B. Compound according to item 1. 92. The compound according to claim 1, which is 2-(4-chlorophenyl)-2-hexyloxy-5-(ikendacyl-1-yl)-propionitrile, hydrogen salt. 93. The compound according to claim 1, which is 2-(4-chlorophenyl)-2-hexyloxy-6-(imidazol-1-yl)-zolobionitrile, malhydrogen. 94, General formula ■: N [wherein, B it /'rogen atom, (C1-C4)-alkyl group, (C-c, )-alkoxy group, (C-04)
- represents the same or different aromatic hydrocarbon group which may be substituted one or more times by an alkylthio group, a trifluoromethyl group or a nitro group, R is a (C1-CIO)-alkyl group, (C3 ~C3)
-alkenyl m, (Cs-C3)-fulkynyl group, represented by λ or halogen atom, (01-04)-alkyl group, (01-04)-alkoxy group, (C□-C4)-alkylthio group, lJ fluoromethyl A process for producing imidazolyl-norovionitrile represented by the general formula: % formula % [wherein the formula: A compound represented by the formula: 1. A method for producing imidazolyloop gastric bionitrile of general formula 1, which comprises reacting the imidazole with imidazole in the presence of a solvent and optionally a base. 95, general formula: CN [wherein R is a halogen atom, (C1-C4)-alkyl group, (C
1-C', )-alkoxy group, (C'l-C', )
- represents the same or different aromatic hydrocarbon group optionally substituted one or more times by an alkylthio group, a trifluoromethyl group or a nitro group, Ro is a (C1-CIO)-alkyl group, (c, ~c8)
-alkenyl group, (C,~Co)-alkynyl group or halogen atom, (C0~c4)-alkyl group, cc'l-C,)-alkoxy group, (C0~C4)-
contains at least one imidapril-probionitrile represented by 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; : Features: Disinfectant. 96. The fungicide according to claim 95, which has a fungicidal action. 91. 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 monocide according to claim 95, which is mixed with a carrier and/or an auxiliary agent.