CS255899B2 - Fungicide and process for preparing active compounds - Google Patents

Abstract

The invention relates to novel homopropargylamine derivatives of the formula <IMAGE> in which a) R1 stands for a group of the formulae <IMAGE> and R2 stands for hydrogen or a lower alkyl group, where R6 and R7 are identical or different and in each case denote hydrogen, halogen, the trifluoromethyl group, a lower alkyl group or a lower alkoxy group, s stands for an integer from 3 to 5 and X stands for oxygen, sulphur, the -O-CH2- group, the -S-CH2- group, the methylene or an -N-R8- group, where R8 denotes hydrogen or a lower alkyl group, R3 and R4 can be identical or different and in each case stand for hydrogen or a lower alkyl group and R5 stands for hydrogen, an alkyl group, an alkenyl group, a trialkylsilyl group, a dialkylphenylsilyl group or a phenyl group, where phenyl groups and alkyl groups can be substituted by the hydroxy group, a lower alkyl group, a lower alkoxy group, the phenyl group or halogen, or b) R3 forms a -(CH2)u group with R4, where u denotes an integer from 3 to 5, R1 stands for a group of the formulae IIa to IIc and R2 stands for hydrogen or a lower alkyl group and R5 has the above meaning, and their acid addition salts, and also processes for the preparation of these compounds and their acid addition salts and their use.

Description

The present invention relates to a fungicidal composition comprising as active ingredient a hopropargylamine derivative of the formula I and a process for the preparation thereof. .

A fungicidal effect has not been known to date for compounds belonging to the general group of allylamines, propargylamines, homoallylamine or hompropargylamines. Some compounds of this general group are known as pharmaceutical compositions. For example, U.S. Patent No. 4,282,251 discloses trans-N-cinnamyl-N-methyl- (1-naphthylmethyl) amines and their use as antifungal agents.

The compounds of the invention are useful in combating phytopathogenic fungi and fungi.

The invention relates to the first homopropargylamine derivatives of the general formula I

(I) wherein n is 2 or 3 is a group of formula

Ha lib cheek

where it means

R? hydrogen, halogen or C 1-6 -alkyl 3, with an integer of from 3 to 5, and

X is an oxygen, sulfur, or -OCH 3 - group, and

R _{2 is} hydrogen or C 1-6 alkyl, and either

R ₃ and R ₄ are identical or different and denote hydrogen or C ₁ _ ₅ alkyl group, or R ₃ and R ₄ form "/ _CH2 / u" the bromo group, wherein u is an integer from to 5 and

phenyl-, cycloalkyl-, and alkyl groups may be substituted by hydroxyl, C _1-5 alkanol or halogen, and their acid addition salts. The invention further relates to a process for the preparation of these compounds and to their use.

According to the invention, compounds of formula I are prepared and / by reacting a compound of formula III

R '- C - NH - R.

i 4

III

A - / СН ₂ / _п - C C - R ₅ / IV / wherein _R5 and n are defined above and A represents a leaving group.

b) Compounds of formula (Ia) and ^R 2 (1a) wherein, when an is as defined above and R ⁷ is a dialkylphenylsilyl, trialkylsilyl or alpha-hydroxyalkyl group, are prepared by metallizing a compound of formula V

/ СН- / - C n

(V) wherein up to R1 and n are as defined above and reacted with the corresponding carbonyl, dialkylphenylsilylhalogen or trialkylsilylhalogen compound.

Compounds of Formula Ib.

RR · ' ¹ ' ⁴ ii

_R2 - C - N - / СН ₂ / _п - С = C - R $ / lb / «3 wherein R ^ to R ^ and n are as defined above and R ¹ is an alkenyl group, is prepared by the of the compounds of formula (Ia) wherein r 1 If desired, the functional groups in the reaction may be protected by appropriate protecting groups, which are cleaved again after the reaction is completed, and the compounds of the formula I obtained are optionally converted into their acid addition salts.

The process a / according to the invention may optionally be carried out in a solvent inert under reaction conditions such as a lower alcohol, for example ethanol, optionally mixed with water, an aromatic hydrocarbon such as benzene or toluene, a cyclic ether such as dioxane, or a carboxylic acid dialkylamide such as dimethylformamide. The reaction temperature is between room temperature and the boiling point of the reaction mixture. The process is preferably carried out in the presence of an acid binding agent, for example an alkali metal carbonate such as sodium carbonate.

The process b) according to the invention can be carried out, for example, in an inert solvent (under reaction conditions), for example in a cyclic ether such as tetrahydrofuran while limiting access to water, preferably at low temperature.

The cleavage of water according to method 5 may be carried out by known methods, for example p-toluenesulfonic acid or mesyl chloride in the presence of a base such as triethylamine and in a solvent inert under reaction conditions such as dichloromethane.

The compounds of formula I may be converted to their acid addition salts and vice versa.

In the preparation of the compounds of the formula Ib, mixtures of cis / trans isomers can be obtained which can be separated by known methods.

The alkyl groups may be straight or branched and contain 1 to 12, preferably 1 to, and especially 1 to 5, carbon atoms. The lower alkyl groups mentioned as substituents preferably contain from 1 to 4 carbon atoms and in particular are methyl and ethyl. Alkenyl preferably contains 3 to 6, in particular 3 or 4, carbon atoms and, for example, is allyl or propenyl. Cycloalkyl preferably contains 3 to 6 carbon atoms.

In the compound of formula (IV), A is, for example, halogen, in particular chlorine or bromine, or an organic sulfonyloxy radical having 1 to 10 carbon atoms, for example alkylsulfonyloxy, preferably 1 to 4 carbon atoms such as methylsulfonyloxy tosyloxy.

The compounds of the invention in free form or in acid addition salts suitable for agriculture are suitable for controlling phytopathogenic fungi. Good fungicidal efficacy results, inter alia, from the in vivo test against Uromyces appendiculatus (bean rust) on bar beans as well as against other rust fungi (Puccinia) on wheat and against Erysiphe cichoracearum on cucumbers and against other powders / Е. Graminis sp. tritici, Podosphaera leucotricha, Uncinula necator / on wheat, apples and vines at a test substance concentration of 0.5 to 500 ppm.

Since the compounds have also been shown to be well tolerated by plants, the compounds of the invention are useful in the control of phytopathogenic fungi, for example to combat Basidiomycetes of the order Uredinales (rust) such as Puccina spp., Hemileia spp., Uromyces spp. and Ascomyteces of the order Erysiphales such as Erysiphe spp., Podosphaera spp. and Uncinula spp.

The amount of the compounds used according to the invention depends on various factors such as the species of the compound of the invention, the subject (plants, soil, seeds), the treatment method (spraying, dusting), the purpose of the treatment (prophylactic or therapeutic). .

In general, satisfactory results are obtained when the compound of the invention is used in the treatment of plants or soil in an amount of from about 0.005 to 2, preferably from about 0.01 to 1 kg / hectare. The treatment may be repeated, if desired, for example at an 8 to 30 day interval. When the compound is used for seed treatment, generally satisfactory results are obtained when the compound is used in an amount of from about 0.5 to 0.5, preferably from about 0.1 to 0.3 g / kg seed.

By the term soil is meant any growth medium, ie soils either natural or artificial.

The compounds of the invention can be used for a variety of crop plants, for example, soybean, coffee, ornamental plants (among others geraniums, roses), vegetables (among other peas, cucumbers, celery, tomatoes and beans), sugar sponge, sugarcane, peanuts , corn, grapevine., for fruit / apples, pears, plums, bananas / and for grain / eg. wheat, rye, barley.

The invention therefore also relates to a method of controlling phytopathogenic fungi, characterized in that the fungi or their environment are treated with a fungicidally effective amount of a compound of the formula I in free form or in the form of an acid addition salt suitable for agricultural use.

The invention further relates to fungicidal compositions comprising as a fungicide a compound of the invention in free form or in acid addition salt form, together with agriculturally acceptable diluents and optionally other excipients such as surfactants. Generally, the compositions contain from about 0.000 to about 90, for example, from about 0.001 to about 70 weight percent of the active ingredient.

Diluents are agriculturally acceptable liquid or solids which are suitable for converting the active ingredient into a better or more applicable form, for example by solution to the desired or required degree. Examples of such diluents are talc, kaolin, diatomaceous earth, xylene and water.

preparations, especially those used in the form of sprays, such as water-dispersible concentrates or wettable powders, may contain surfactant compounds (e.g. up to 20% by weight) as wetting or dispersing agents, for example, the condensation products of formaldehyde and naphthalene sulfonate, alkylarylsulfonate , lignin sulphonate, alkyl sulphate, ethoxylated alkylphenol or ethoxylated fatty alcohol.

Examples of fungicidal compositions are described below (parts by weight).

a) A wettable powder of parts of the compound of formula I is milled with 2 parts of lauryl sulphate, 3 parts of sodium lignin sulphonate and 35 parts of fine kaolin until the mean particle size is less than 5 µm.

b) Granular preparation

94.5 parts by weight of quartz sand are sprayed in a drum mill with 0.5 parts by weight of binder (non-ionic surfactant) and mixed thoroughly. 5 parts by weight of the compound of the formula I are added and mixed vigorously until a granular preparation is obtained in the particle size range up to 0.3 to 0.7 mm.

The emulsion concentrate of parts by weight of the compound of the formula I is mixed with 30 parts by weight of iso-octyl octaglycol ether and 45 parts by weight of a petroleum fraction having a boiling range of 210 to 280 ° C ^{/ D} 20 = ° - ⁹² ° · d / of formula I is mixed with 1.5 parts of ethylene oxide / diamylphenol decalglycol ether addition product, 2 parts of spindle oil, 51 parts of finely ground pressure and 0.5 parts of Rhodamine B. The mixture is ground in a Contraplex mill at 10,000 rpm until the average particle size is not less than 20 µm. The dry powder thus obtained has good adhesion and can be added to the seeds or seed, for example by mixing for 2 to 5 minutes in a slowly rotating drum.

In preferred compounds of formula I, the substituents have one or more of the following meanings:

R @ 1 = Ha or J. Ib

X = O or S

R.? H, halogen (especially Cl or Br) or C 1-6 alkyl (especially CH 2)

_Of R - H or C ^ - ^ alkyl

R = H, or together with R ^ / C ^ / ^ ^R 4 ^C l-4 ^alkyl, H, C ^ _galkyl / in particular C ^ alkyl ,. _ /, C ^^ cycloalkyl of 1, C ₃ _ ^ alkenyl, C _ alkoxyl ^ -C ^ _ ^ alkyl, phenyl-C ^^ alkyl, halophenyl-C ^^ j ^ alkyl, hydroxy-C ^^^ alkyl, tri / C ₁ _ ₅ alkyl / silyl, di / C ₁ _ ₅ alkyl / phenylsilyl.

In more preferred compounds of formula I, they are substituents

R (1) -naphthyl, benzofuranyl or benzothiophenyl, unsubstituted or monosubstituted by halogen or _z , alkyl,

R ^, R ^ is each H,

R is CH ₃ or C _r H ,, especially CH _O ^J 3 2 5 3

R represents H, C ₃ _ ₆ cykloalky1 or tertiary carbon atom bonded to homopropargylovou group selected from the groups consisting _{С] и4 а1коху С-3} _ ₅ а1ку1, halophenyl-C ^^ alkyl, phenyl ~ ₃ _ ₅ alkyl, hydroxy t -C? -alkyl, and C 1 _ ₃ alkyl,

The starting compounds are either known or can be prepared by known methods or by procedures described in the examples.

The following examples illustrate the invention in more detail. Tetplots are given in degrees Celsius. Example 1

N-Methyl-N- (1-naphthylmethyl) -5,5-dimethyl-3-hexin-amine (method a)

A solution of 540 mg of 5,5-dimethyl-3-hexin-1-ol in dimethylformamide was added to 1.2 ml of triethylamine at 0 °. Methanesulfonyl chloride (0.335 ml) was then added dropwise with stirring. After stirring at room temperature for 2 hours, 740 mg of N-methyl-1-naphthylmethanamine was added and heated to 80 ° C overnight. The solvent was evaporated in vacuo, the residue partitioned between saturated aqueous sodium bicarbonate solution and ethyl acetate, the organic phase was washed, dried and evaporated. The crude product is chromatographed on silica gel (toluene: ethyl acetate = 9: 1). The title compound was obtained as an oil.

The following compounds of the formula I shown in Table 1 can also be obtained analogously to Example 1.

Tabulkal.

Example ^R 1 ^R 2 ^R 3 ^R 4 ^R 5 n phys 2 1 1 1 H H ^CH 3 2 oil 3 i l 1 H H ^CH 3 H 2 oil .4 к C ¹ H H ^CH 3 ^CH 3 iX ⁵ 2 oil 5 к Ci H H ^CH 3 ^CH 3 -c-Lh, I 6 6 ^CH 3 2 m.p. (HCl): 106-110 ° 6 к И И ⁰ Br H H CH ₃ - ^{C (CH} 3> 3 2 oil 7 - 'Y' s' H H CH ₃ -C (CH ₃ ) ₃ 2 m.p. 35 to 37 ° 8 <Ci H - (CH 2 * 4 " - ^{C (CH} 3> 3 2 m.p. 82 to 84 ° Cl 9 - II II H H ^CH 3 -С (СН ₃ ) ₂ 2 m.p. 62-64 °

Table 1 continued

Example ^R 1 ^R 2 ^R 3 10 Cl О '· .— ^/ 1. H II 1 ^p H H 11 1 к l> H H 12 , 1 O '. ^ <5. Ш H H 13 H H 14 О '· .-- il | 11 V / kn / X ^with Cl H H 15 Dec 1 ___ '!' No. H H

^R 4 ^R 5 n phys ch ₃ H 2 oil ^CH 3 ^C 6 ^H 5 2 oil ^CH 3 -C 10 _O H _c 1 ^{2 5} CH ₃ 2 oil CH ₃ -C (CH ₃ ) ₃ 2 oil CH ₃ "C (CH3) ₃ 2 oil CH ₃ -C (CH ₃ ) ₃ 2 m.p. (HCl): 205-208 °

---

I ll ll Η H

CH ₃ ¹⁷ i И || J Η h

18 'к M Η Η 19 Dec к / Ύ5 Η Η 20 May 1 к II> сн ₃ Η 21 1 LI ¹ /! Η Η / 22 what | Η Η 23 1 к! ' · ' Η Η

сн ₃ -с (с ₃ ) ₃ 2 m.p. (HCl): 185 to 190 ° ^сн з -С (СН ₃ ) ₂ 2 oil. сн ₃ CHq '' · = '· v // сн ₃ F ^С 2 ^Н 5 -С (СН ₃ ) ₂ 2 oil ^сн з -С (СН ₃ ) ₂ 2 oil СН ₃ _ / м \ \ 1 / 2 oil н -С (СН ₃ ) ₂ 2 oil ^сн з -С (СН ₃ ) ₂ 2 oil

-255899

Table 1 continued

Example ^R 1 ^R 2 ^R 3 ^R 4 ^R 5 n phys 24 . 1 к! ' J No. H CH ₃ (ch ₃ 3 oil AND OH 25 к o H II CH ₃ -C (C ₂ H ₅ ) ₂ 2 oil 26 . . 1 к M H H ^CH 3 OH -C- _{C 3} H ₃ ^CH 3 2 oil 27 Mar: к O H H CH ₃ ? ^H 3 -? - ^C 6 ^H 5 ^CH 3 2 oil 28 . I, to C ¹ H H ^CH 3 -Si- (CH ₃ ) ₃ 2 oil 29 . 1 к M H H ^CH 3 C = CH-CH, 1 J ^C 2 ^H 5 2 oil

Example 30

N-Methyl-N- (1-naphthylmethyl) -5-ethyl-5-hydroxy-3-heptin-aniline (method b)

To 2 g of N-methyl-N- (1-naphthylmethyl) 3-butylamine in absolute tetrahydrofuran was added dropwise at -70 ° 5.6 ml of a 15% solution of n-BuLi in hexane and after half an hour at 0 ° C was added. , 95 ml diethyl ketone. Stir for three hours at room temperature, then poured onto ice and extracted with ether. The organic phase is washed, dried and evaporated in vacuo. After chromatography on silica gel (toluene: ethyl acetate = 3: 1). The title compound was obtained as an oil. ·

Using the procedure of Example 30, the compounds of Examples 26, 27 and 28 can be obtained.

Example 31

N-Methyl-N (1-naphthylmethyl) -5-ethyl-5-hepten-3-ylamine (method с)

To a solution of 630 mg of N-methyl-N (1-naphthylmethyl) -5-ethyl-5-hydroxy-3-heptinamine in dichloromethane is added dropwise at -20 ° 0.5 ml of triethylamine and finally 0.21 ml of mesyl chloride dissolved in dichloromethane. It is then stirred for three hours at room temperature, shaken several times with water, the organic phase is dried and evaporated. The residue is chromatographed on silica gel (toluene: ethyl acetate = 4: 1). The title compound was obtained as an oil.

Example 32

Table 2 shows the fungicidal activity assays of selected compounds of the invention.

bulka 2

ЕС 90 * in mh / 1

Example # 1 4 5 14 15 Dec 18 19 Dec 27 Mar: 28 Mushroom Plant Erysiphe cucumber 525 2 12 8 11 <0.5 1 4 4 Podosphaera apple 8 6 12 8 11 33 3 8 9 Erysiphe wheat ]. 1 11 11 103 1 1 3 3 10 9 Uncinu.la Grapevine 11 9 11 6 9 8 3 1 1 ] 0 Uromyces bean Šarl. . 3 5 <0.5 0.7 <0.5 0.8 36 / o> 4 0.9 Puccinia trit. wheat 101 6 3 3 2 1 0 27 Mar: 5 11 9

ЕС 90 concentration in mg / l allowing 90 i control

Spectrum (CDC1 _3, TMS):

8.2-8.4 (m, IH); 7.65-7.95 (m, 2 H); 7.25-7.6 (m, 4H); 3.93 (s, 2 H); 2.25-2.8 (m. 4H);

2.24 (s, 4H); 1.18 (s, 9H).

8.25-8.45 (m, IH); 7.7-7.95 (m, 2 H); 7.3-7.65 (m. 4H); 5.1-5.3 (m. 2H); 3.98 (s, 2 H);

2.45-2.95 (m, 4H); 2.3 (s. 3H); 1.9 (m, 3H).

8.2-8.4 (m, IH); 7.6-7.9 (m. 2H); 7.2-7.6 (m, 4H); 3.9 (s. 2H); 2.2-2.9 (m. 4H);

2.26 (s, 3H); 2.0 (t, J = 2 Hz, 13).

8.2-8.4 (m, 1 H); 7.7-7.95 (m, 2H); 7.25-7.6 (m 4H); 3.96 (s, 2H); 2,3-2,8 (m, 4H); 2.25 (s, 3H); 1.4 (pseudog, 2H); ; 1.14 (s, 6H); Oj 95 (t, J = 7 Hz) 3H). 8,25-8,4 (m, 1 H); 7.7-7.95 (m, 2H) _? 7.2-7.65 (m 9H); 3.97 (s, 2H); 2,4-2,9 (ir, 4H); 2.28 (s, 3H); 1.55 (s, 6H). 7,65-7, 85 (m, 1 H); 7.1-7.5 (m, , 3H) ; 3.6 (s, 2H) ; 2.2-2.75 (m, 4H); 2.22 (s, 3H); 1.18

(s, 9H).

7.65-7.85 (m, 1 H); 7.2-7.5 (m. 4H); 3.8 (s. 2H); 2.3-2.8 (m, 4H); 2.25 (s. 3H); 1.18 (s, 9H).

8.4-8.7 (broad, 1H); 7.25-7.95 (m, 6H); 3.7-4.0 (m, IH); 3.2-3.4 (dbr, J = 11Hz).

1H); 2.55-2.8 (m, IH); 2.0-2.4 (m, 4H); 1.4-1.9 (m, 6H); 1.1 (s, 9H).

7.78 (dd, J 1, 2Hz, 1H); 7.46 (d, J = 7HZ, 1H); 7.3 (s, 1 H); 7.3 (d, J = 7 Hz, 1H);

3.82 (s, 2 H); 2.3-2.8 (m, 4H); 2.24 (s, 3H); 1.18 (s, 9H).

7.78 (dd, J = 7 and 2Hz, 1H); 7.46 (d, J = 7 Hz, 1H); 7.3 (d, J = 7 Hz, 1H) δ 7.3 (s, 1H);

3.8 (s, 2H); 2.3-2.8 (m, 4H); 2.24 (s, 3H); 1.96 (t, J = 1 Hz, 1 V).

8.25-8.45 (m, IH); 7.7-7.95 (m, 2 H); 7.2-7.6 (m, 9H); 3.98 (s, 2 H); 2.5-3.0 (m, 4H);

2.3 (s, 311).

8.2-8.4 (m, 1H) i; 7.7 -7.95 (m, 2H); 7.3-7.6 (m, 4H); 3.95 (s, 2 H); 3, _4, 58 (q, J = 7Hz, 2H); 2, 35-2.85 (m, 4H); 2.28 (s, 3H); 1.42 (s, 6H); 1.18 (t, J = 7 Hz, 3H). 7.8-8.1 (nI, 2H); 7, 2-7, 5 (m, 3H); 3.78 (s, 2H); 2.3 -2.6 (m, 4H); 2.28 (s, 3H); 1., 2 (s, 911) 7.8-8.1 (m, 1 H); 7, 6-7.8 (m, 1H); 7.2-7.5 (m, 2H); 3.76 (s, 2 H); 2,3-2,8 (m, 4H); 2.2 2 (s, 3H); 1.2 (s, 9H).

7.82 (m, IH); 7.72 (dd, J = 5.5 µ, 1Hz, 1H); 7.45 (d, J = 5.5 Hz, 1H); 7.32 (d, J = 5.5 Hz, 1H); 7.3 (m, IH); 3.84 (s, 2 H); 2.3-2.8 (m, 4H); 2.22 (s, 3H); 1.2 (m, 9H).

7.7-8.0 (m, 2H); 20 (s, 7.2-7.5 (m, 9H). 2H); 3.68 (s, 2 H); 2.3-2.8 (m, 4H); 2.56 (s, 3H); 2,20- (s, 3H); 1, 6.95-7.2 (m 3H); 3.55 (s, 2H) ; 2, 7-2.95 (m. 4H) ; 2.3-2.7 (m, 4H) 2.22 (s, 3H): 1,8-2,0 (m, 4H); 1.20 (s, 9H). 8.2-8.4 (m, 1H); 7.7-7.95 (m, 2H) ,3 7.3-7.6 (m, 6H); 6.96 (t, J = 9Hz, 2H); 3.96 (s, 2H); 2, 4-2,9 (m, 4H); 2.28 (s, 3H); 1.52 (s, 6H). .

8.25-8.45 (m, IH); 7.7-7.95 (m, 2 H); 7.25-7.6 (m, 4H); 4.02 (s, 2 H); 2.2-2.8 (m,

4 + 2H); l, 16 (s, 9H); 1.06 (t, J = 7Hz, 3H). 8,3-8,5 (m, 1H); 7.3-7.95 (m, 6H); 4.35 (g, J = 7 Hz, 1H); 2.2-2.8 (m. 4H); 2.3 (s, 3H) 1.48 (d, J = 7Hz, 3H); l, 18 (s, 9H). 8.2-8.4 (m, 1H); 7.7-7.95 (m, 2H); 7.25-7.6 (m, 4H); 3.94 (s, 2 H); 2.2-2.8 (m, 5H); 2.26 (s, 3H); ? 1.1 -2.0 (m. 10H) • 8.1-8.3 (m, 1H); 7.7-8.0 (m. 2H); 7 , 2-7.65 (m. 4H); 4.25 (s, 2 H); 2.2-3.0 (m, 4H); 1,8

(br, NH); 1.15 (s, 9H).

6.7-7.4 (m, 4H); 5.7 (m, IH); 4.7 (m, 2 H); 3.20 (m, 2 H); 2.3-2.8 (m, 4H); 2.2 (s. 3H);

1.2 (s, 9H).

8.25-8.45 (m, IH); 7.7-7.95 (m, 2 H); 7.25-7.6 (m, 4H); 3.88 (s, 2 H); 2.58 (t, J = 7 Hz); 1.6-1.9 (m. 2H); 1.16 (s, 9H).

8.2-8.4 (m, IH); 7.7-7.95 (m, 2 H); 7.25-7.65 (m, 4H); 3.94 (s, 2 H); 2.35-2.85 (m,

4H); 2.28 (s, 3H); 1.8 (broad); 1.65 (g, J = 7.5 Hz, 4H); 1.0 (t, d = 7.5Hz, 6H).

8.2-8.4 (m, IH); 7.65-7.95 (m, 2 H); 7.25-7.6 (m, 4H); 3.9 > 2 (s, 2H); 2.3-2.8 (m, 4H); 2.24 (s, 3G); 1.85 (broad); 1.44 (s, 6H). .

8.2-8.4 (m, IH); 7.2-7.95 (m, 11H); 3.95 (s, 2 H); 2.4-2.9 (m, 4H); 2.26 (s, 3H);

0.4 (s, 6 H).

8.2-8.4 (m, IH); 7.7-8.0 (m. 2H); 7.3-7.65 (m. 4H); 3.90 (s, 2 H); 2.25-2.8 (m. 4H); 2.25 (s. 3H); 0.2 (s, 9H).

8.2-8.4 (m, IH); 7.65-7.95 (m, 2 H); 7.2-7.6 (m, -4H); 5.5-5.9 (m, IH); 3.95 (s, 2 H); 2.45-2.9 (m, 4H); 2.27 (s, 3H); 2.1 (gm, J = 7 Hz, 2H); 1.8 (m, 3H); 1.04 (t, J = 7 Hz, 3H).

Claims (7)

OBJECT OF THE INVENTION * A fungicidal composition comprising, as an active ingredient, a compound of the formula I hh R - C - N ² I R ₃ ^{/ CH} 2 ^Z n / I / 2 or 3, wherein n has a value. R ₃ is a group of the formula wherein R ₃ is R _{7 is} hydrogen, halogen or C 1-6 -alkyl, with an integer from 3 to 5, and X an oxygen, sulfate, or -O-CH 2 - group, and R ₂ and R ₄ are the same or different and are hydrogen or C 1-6 -alkyl, or R ₄ and R ₄ form a - (CH ₂ ) _u - group wherein u represents an integer from 3 to 5 α И - represents hydrogen, C_ ^ alkyl, C ^^ - alkyl, cycloalkyl, C ^^ alkenyl, tri (C | _ ₅ alkyl) -silyl, di (C ^^ alkyl) fenylsilyllovou, phenyl or phenyl С ^ _ ₅ а1куlovou group wherein the phenyl, cycloalkyl and alkyl groups may be substituted with a hydroxyl, C 1-4 alkoxy or halogen group, and acid addition salts thereof. 2. A fungicidal composition as claimed in claim 1, wherein the active ingredient is a compound of formula (I) wherein n is 2; R is hydrogen, C ₁ _ ₅ alkyl, C ₂ _ ^ alkenyl, tri (C ^^^ alkyl) silyl, di (C j ^ alkyl) phenylsilyl or phenyl and R _1, R _2, R, R ₄ , R _? , X s, au shall have the meaning given in point 1. 3. A fungicidal composition according to claim 1, characterized in that it comprises as active ingredient a compound of formula I wherein n is 3 and R ^, R _4> R, R ?, X, Sau have the meanings given in point 1 . 4. A fungicidal composition according to claim 1, wherein the active ingredient is a compound of formula (I) wherein n is 2; R - represents a C ^^ cycloalkyl, phenyl-С ^ _ ^ halophenacyl alkyl or 1-C ^ _ _(.alkyl and R @ ₁ , R @ ₂ , R @ ₄ , R @ ₄ , Ry, X, s and u are as defined in 1. 5. A fungicidal composition according to claim 2, wherein the active ingredient is a compound of formula (I): R1 is a group of formula IIa or IIb, X is O or S, R y is H, halogen or C 1-4 alkyl, R is H, or C ^ _ ₄ alkyl, either is H and R ₄ is C ^^ alkyl, or R together with R ₄ is / СН _2/4 and RJ is H, C ^ _ ^ alkyl, C ₃ _ ^ alkenyl, C ^ _ ₄ alkoxy-C ^ _ ^ alkyl, hydroxy-C ₃ _ _c -a plurality of projections 1, class II (C, _ alkyl) phenylsilyl. 6. A fungicidal composition according to claim 5, wherein the active ingredient is a compound of formula (I) wherein: R ₃ represents 1-naphthyl, benzofuranyl or benzothiophenyl, unsubstituted or monosubstituted with halogen or C _1-4 alkyl, R ₂ and R ₃ represent H, Cf__ ₄ represents alkyl and R ₃ represents H, or a tertiary carbon atom bonded to homopropargyl group selected from the group consisting Cf_ ₄ alkoxy-C ^^ alkyl, hydroxy-C ₃ _ ₅ alkyl, or C ^^ alkyl. by 7. that ^R 2 A process for the preparation of the compounds of the formula I according to claim 1, characterized in that it is reacted - C - NH - R, I ⁴ R _{3 is a} compound of formula III (III) wherein ^R 1 through are as defined in item 1, with a compound of formula IV wherein A - / с ₂ / _п - c = c ^R 5 / V / R 8 and n are as defined in 1 and A represents a leaving group. Severography, n. P., MOST Price 2,40 Kčs