CS236480B2 - Agent with fungicide and bactericide effect - Google Patents

Abstract

Novel imidazolylpropionitriles of the general formula <IMAGE> in which R represents an aromatic hydrocarbon radical that is unsubstituted or substituted by one of more of the same or different substituents selected from halogen atoms, (C1-C4)- alkyl, (C1-C4)-alkoxy and (C1-C4)-alkylthio radicals and trifluoromethyl and nitro groups, and R1 represents a (C1-C10)-alkyl, (C3-C8)-alkenyl, (C3-C8)-alkynyl or phenylalkyl radical each of which is unsubstituted or substituted by one or more of the same or different substituents selected from halogen atoms, (C1-C4)-alkyl, (C1-C4)-alkoxy and (C1-C4)-alkylthio radicals and trifluoromethyl and nitro groups, and their acid addition salts with inorganic and organic acids, possess a fungicidal, growth-regulating and bactericidal action.

Description

The present invention relates to a composition and a fungicidal and bioconticidal activity comprising the novel imidiooylppooPoitriles and their salts with inorganic and organic acids and their preparation.

It has also been disclosed that it is immunocomponent and fungicidal. the effects are already known. (DOS 26 04-047). These trains have a relatively narrow spectrum - efficiently, which is impressive.

SUMMARY OF THE INVENTION It is an object of the present invention to provide novel imdaolylppolioo0101. - A wide range of applications, particularly in the field. plant protection and - which should have a broad spectrum efficiency.

This object is achieved by a composition according to the invention which contains, as active principle, the imooloolylprolithiol of the formula I.

Ο-R,

I / =?

r-c_ch ₂ -n (I),

CN

Even in which

R denotes phenA, haloanphthalene, dichlorophane, m-thiophenes. . or meehooypharous,

R 1 represents C 1 -C 10 alkyl, alpha 1 or benzyl. and their (d) salts and inorganic and - organic acids.

Compounds beneath VYN ^ Climbing fungicidal and laιkt · ^to icitaě effective. In particular, they are characterized by an effect of function, in which, surprisingly, they exceed the known active substances analogous to fat and direction.

The fungicidal effect of ee (14) (10) (16) refers to fungi of different systematic care. The over-treatment of above-ground plants protects the pathogen from the pathogens transmitted by the wind. Compounds may be used to treat seed against agents of seeding seed. In addition, it acts systemically, i.e., the plant roots are taken up, for example, after application, are transferred to the above-ground parts of the plant and protect themselves against the causative agents.

Another effect is the lactoidal effect.

Because of the broad spectrum of efficacy disclosed herein, the compounds of the present invention are suitable for the protection of cultured plants, but also for the protection of material and the destruction of pathogens pathogenic to humans and animals, thereby providing a wide range of benefits.

Always after the special significance of tubititites, it is essential - at the same time it is essential! - uses in which the compounds whiten the blowing effects. The compounds may be used as fungicides or as

In the compounds represented by the general formula (I), they may for example be:

R 5 -fluoro-1,4-fluoro-4-chloro-4'-S-chlorophenyl, 4-fluoro-4'-fluorophenyl,

S-brominated, З-пмпГ «пЛ, 4-1юш1 ^ 1 ^ 1П ^ 1. ₉ S-iodine, 3-iodo-iodo-1,2,3-dichlorophenyl, 2,4-dichlorophenyl, 3,4-dichlorophenyl, S-dichlorophenol, 2,4-dichlorophenyl, 2,4-dichlorophenyl, 2,4-dichlorophenyl 3-methylphenyl-4-methylphenyl, 1,3-methoxyl, 4-methylphenyl, and

23М80

Н | ^{с Г вС ю} alkyl such as methyl, ethyl, propyl, butyl, pentyl, heptyl, octyl, nonyl, decyl, isopropyl, 2,2-dimethyl-1-propyl, 3,3-Dine '2-methyl-butyl, allyl n <sbo benzyl ·

Examples of inorganic organic acids for the formation of addition salts are hydrohalic acids, such as hydrochloric acid and hydrobromic acid, phosphoric acid, sulfuric acid, in particular nitric acid, monofunctional and functional carboxylic acids and hydroxycarboxylic acids. such as acetic acid, aaleinovou acid, succinic acid, fumaric acid, tartaric _g citric, salicylic, p sorbic acid, lactic acid, and sulphonic acids such as p-toluenesulfonic například.kyselinu acid and 1,5-naftalendisulfonovoue

These acid addition salts may be obtained by conventional methods, for example by the reaction of a compound of formula I in a suitable solvent and the addition of an acid.

Among the compounds according to the invention, the fungicidal activity is characterized by those in which, in the general formula (I), the radical R denotes a phenyl radical optionally one or more times _r , the same or differently substituted by halogen, methyl or methoxy.

R 6 is (C 1 -C 6 alkyl, allyl or benzyl)

It is preferable to mention those compounds in which they are present

R is phenyl, 2-chlorophenyl _? i-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 4'-chlorophenyl, 3,4-dichlorophenyl, 2-fluorophenyl, 4-fluorophenyl, 4-bromophenyl, 2-methylphenyl, 4- methylphenyl, 4-methoxyphenyl and a

R | methyl, ethyl, propyl, isopropyl, panyl, hexyl, allyl bensyl ·

The following compounds of the invention have a significant effect

2'-n-butoxy-2- (2'-chlorophenyl) -3- (imidazol-1-yl) propionyltril hydronitrate, 2-> n.-butoxy-2'- (2-chlorophenyl) -3- (imidazol-1) 2-n-butoxy- (4-chlorophenyl) -3- (azidazol-1-yl) propionitrile, hydronitrate

2- (4-chlorophenyl) -3- (imidazol-uyl) -2-n-propoxypropionitrile hydronitrate

2- (2-chlorophenyl) -3- (imidazol-1-yl) -2-n-propoxypropionitrile

In particular, the compounds of the present invention exhibit fungicidal activity, but are also growth regulators in many crop plants

As already mentioned, the compounds of the invention and e are transferred in the field.

Accordingly, they exert a growth-regulating effect both when applied above ground and in spray treatment.

Especially noticeable is the growth suppression of cress and cotton ·

In addition to the above-mentioned effects, the compounds according to the invention also exert a bactericidal effect which allows for further application.

The compounds according to the invention may be used either as an adjuvant, in admixture with one another or with other active substances. If necessary, other plant protection or pest control agents can be added depending on the desired purpose.

Suitably, the active compounds or mixtures thereof are used in the form of preparations such as powders, dusts, granules, solutions, emulsions or suspensions, with the addition of liquid or solid carriers or diluents and, if appropriate, tackifiers, emulsifiers and / or agents Suitable liquid carriers are, for example, water-aliphatic and aromatic hydrocarbons such as benzene, toluene, xylene, cyclohexanone, isophorone, di-ethylsulfide, dimetilorethane, further oil and vegetable oils.

Suitable solid carriers are suitable. tonssi, 3X11-8, maeltelk, kaolin, ttpulgite, limestone, silicic acid, and plant products such as moiety.

Surfactants include, but are not limited to, such as, but are not limited to, polyolefins, polyphenols, naphthylsulfonic acids and their salts, phenolsulfonic acids and their salts, phymaldehyde concenates, fatty alcohol sulfates, and substituted benzene salts and their benzene acids.

If the active substances are to be used for seed dressing, coloring agents can also be added to give the seed to be picked up well recognizable in color. The delay of the active substance (s) in the various preparations can be varied in wide mixtures. up to 90 percent by weight of active ingredients, about 90 to 10 percent by weight of liquid or solid carriers, and optionally up to 20 percent by weight of surfactants.

The application of the compositions can be carried out in conventional manner, for example with water as carrier in spray liquors of about 100 to 1000 liters / ha. It is also possible to use the so-called low-volume or ultra-low-volume formulations and to apply them in the form of so-called microgranules. For example, the following components are used to prepare the formulations:

A. · Spray powder

a) 40 percent UmoOnootic

p.rocent osních

20: percent of the percent by weight of the moiety percent 0 ^ 081115 ^

(b) 25. percent less> percent less hOnoOnzlSníi percent less less percent

c) 10 percent by weight of the active ingredient by weight of the minerals of the lightweight pitch silicic acid. surfactants based on a mixture of calcium-ligninsuonic acid with a silicic acid silicate active substance, surfactants based on sodium-N-methyl and sodium lignin sulphonic acid active substances of lime silicic acid mineral minerals The binders of the sodium sulphate-based surfactants are N-II-N-III-tauriz and the calcium salt of Lizo-sulfonic acid.

active substances of cetylpolyglycol ether sodium aluminum silicate and 8 moles of spindle oil of ethylene glycol spindle oil

В. Pastes percent by weight percent by weight percent by weight percent by weight of water

C _o Emulsion concentrate weight percent weight percent weight percent cyclohexanone xylene active ingredient of nonylphenyl polyoxyethylene or calcium dodecylbenzenesulfonan

The compounds according to the invention can be prepared, for example, by propionitrization of the formula II

STEED.

AND

CN in the presence of a solvent and optionally in the presence of a base is reacted with an imidezole of formula

HC-Nfi

HC-CH \ /

N (III) where

R and have the previously mentioned meaning *

The reaction can be carried out either in excess of imidazole, optionally in the presence of a solvent, or with the addition of a strong base such as sodium hydroxide or potassium hydroxide. In addition, an imidazole-alkali metal can also be used in place of imldazole.

Suitable solvents are substances inert to the reactants, in particular of a polar, acetic nature such as N, N-dimethylformamide, Ν, Ν-dimethylaeetemide, N-methylpyrrolidinone, tetromethylurea, hexamethylphosphoric triamide and benzonitrile, but also higher-boiling aromatic and aliphatic hydrocarbons. such as toluene, chlorobenzene or xylene *

The reaction temperature can be varied within a wide range. Preferably, the temperature is between 100 ° C and 200 ° C. The reactions take place under normal pressure or under positive pressure.

The imidazolylpropionitriles of the invention are generally near colorless odorless oils. Their acid addition salts are colorless, crystalline, odorless oils. Oils dissolve poorly in water and more or less well in organic solvents such as alcohols, ethers, or chlorinated hydrocarbons. The acid addition salts dissolve partially in water and dissolve well in polar organic solvents such as acetonitrile, N, N-dimethylformamide, low alcohols, chloroforimide and methylene chloride.

The following examples illustrate the preparation of the compounds of the invention.

Example'

3- (imidazolyl) -2-phinyl-2-proposylpopionitrile, hydrate (Compound No. 1) g (0.053 mol) of 3-methylsulfonyl-2-phenyl-2-propoxyypopionitrile and 17.89 g. Imidazole (0.263 mol) was maintained at 140 ° C for 16 h with the addition of 1 mL dimethylformamide amide, excluding moisture. Spills. The mixture is washed with ice water, extracted twice with 75 ml of methyl chloride, the carbonate phase is washed twice with water, dried over magnesium sulphate and after the drying agent has been filtered off under vacuum. The residual dark oil is dissolved in itopropanol and 100% nitric acid is added. slightly more than a lot of theory. To complete the precipitation, add something of diethyl ether. The precipitated product is filtered off with suction and dried.

Yield: 12 g of 7% of theory

Mp: 168-17 ° C (decomposition)

3) (midazo-1-ll) -2-nitoyl) ~ 2-poopoylpyrooioitrile (Compound No. 2)

6.2 g (0. 0195 moo) of the hydrooate are dissolved in methanol and made basic by diluting with dilute ammonia solution. After dilution with water, extract with ethyl acetate, wash the organic phase with water and then dried with magnesium sulfate. After filtration, it is added under vacuum. The oil remains, which is dried under vacuum.

Yield: 4.85 g = 97% of theory ⁿ £ '= ¹ 526 0

In a similar manner, the successors of the compound of the invention can be produced.

Yes, compounds

3 · 2-butoxy-3- (midzolin-1-yl) -2-phthylpropylnitrile-4-ol

4 · 2-carboxylic acid (3-imidazol-1-yl) -2-phenoxypropylitrile · 2) aliloxy-3) (imidazol-1-yl) -2- (4-propanol) hyfroontrate

6 · 2-alylyloxy-3- (midazo-1-iD-Si-pheniliropiinitil · 2) (1) (1) (3) (imidazzol) 1-yl) -2) (4-propionate), hyphrzoitrate

8 · 2-thiocynyl-3- (imidazol-1-yl) -2iteoyl przopcoittil

9 · 3- (imidoazo- apos; -yl -) - 2- ^ mmttloχy- ieoy.irzpiioittil h ^ <^ i ^ (^ D ^ ii ^ stearate physical constants ыи 155-157 ° C (decomposition) ³⁹ 8 1.520 t, t,: 162-164 ° C (decomposition) ^o 33 ³ «1.540 2 · 182: áž 186 ~ ° C (decomposition)« R * 1,524

189 DEG -19 DEG C. (decomposition)

Name of the compound

10. 3- (Imidazol-1-yl) -2-methoxy-2-phenylpropionitrile

11. 2- (2-Chlorophenyl) -3- (imidazol-1-yl) -2-propoxypropionitrile, hydronitrate

12'-2-butoxy-2- (4-chlorophenyl) -3- (imidazole-

1-yl) -propionitrile, hydronitrate

13. 2-butoxy-2- (2-chlorophenyl) -3- (imidazole-

1-yl) -propionitrile, hydronitrate > 2-allyloxy-2- (2-chlorophenyl) -3-imidazole-

1-yl) -propionitrile, hydronitrate

15 * 2- (4-chlorophenyl) -3- (imidazol-1-yl) -2-propoxypropionitrile, hydronitrate

16. 2-allyloxy-2- (4-trifluorophenyl) -3- (imidazol-1-yl) -propionitrile hydronitrate

17o 2 '(2-chlorophenyl) -3- (imidazol-1-yl) -2-propoxypropionitrile

18 ® 11-butoxy-2- (4-chlorophenyl) -3- (imidazol-1-yl) -propionitrile

9 * 2-butoxy-2- (2-chlorophenyl) -3- (imidazol-1-yl) propionitrile

20 _c 2-Allyloxy-2- (2-chloro-phenyl (imidazol-1-yl) -propionitrile

21. 2 '(4-Chlox- ^1- phenyl) -3- (imidazol-1-yl) -> 2-proposypropionitrile

22. 2-allyloxy-2- (4-chlorophenyl) -3- (imidazole-

1-yl) -propionitrile o 2-Benzyloxy-3- (imidazol-1-yl) -2-phenylpropionitrile

24 * 2-Benzyloxy-3- (imidazol-1-yl) -2-phenylpropionitrile

25- 3- (Imidazol-1-yl) -2-isopropyloxy-2-phenylpropionitrile

_26β 3- (Imidazol-1-yl) -2-isopropyloxy-2-phenylpropionitrile

27 * 2- (4-chlorophenyl) -2-hexyloxy-3- (imidazol-1-yl) propionitrile, hydronitrate

28. 2- (4-chlorophenyl) -2-hydroxyloxy-3- (imidazole-

1-yl) -propiate tri

29.2. Allyloxy-3- (imidazol-1-yl) -2- (2-methylphenyl) propionitrile hydronitrate

30. 2- (3,4-Dichlorophenyl) -3- (imidazol-1-yl) -

2-butoxy-2- (2,4-dichlorophenyl) -3- (imidazol-1-yl) propionitrile, hydronitrate

32 * 2-allyloxy-2- (2,4-dichlorophenyl) -3- (imidazole-

1-yl) -propionitrile, hydronitrate

33 * 2-Ethoxy-2- (3,4-dichlorophenyl) -3-limidazol-1-yl) propionitrile hydronitrate

34. 2-Llyloxy-3- (imidazol-1-yl) -2- (2-methylphenyl) propionitrile

35 * 2 ^ ( _η 4 -dichlorophenyl) -3- (imidazol-1-yl) -

2-propoxypropionitrile physical salts

mp: 57-60 ° C

mp: 162-165 ° C (decomposition)

mp 178-181 ° C (dec.)

mp: 177-178 ° C (decomposition)

mp: 153-155 ° C (decomposition)

mp: 174-557 ° C (roaKLad)

mp: 152-155 ° C (decomposition) ^δ and δ 1.534 3 n '= 1.528 8 n' = 1.532 9

4 '“4549 0 η £' χ 1,533 7“ в * * ¹ »548 6

mp: 166-168 ° C (decomposition) n ⁴ 1,563 8

mp: 165-168 ° C (dec.) n ° x 1.525 4

mp: 552-154 ° C (dec.) <»1.519 7

mp 160 ° C (decomposition)

mp: 169-170 ° C (decomposition)

m.p. 148-150 ° C (decomposition)

mp: 158-160 ° C (decomposition)

mp: 105 to 106 ° C (decomposition) n °> 1.538 δ

a. “1,536 0

Name of the compound

Physical constants

36. 2-AAlyloxy-2- (3,4-dichlorophenyl) -3- (imidazol-1-yl) -propioniiril

37. 2-Buto: γ> 2- (2,4'-dichlorophenyl) -3- (imidezoo-1-yl) -ρ ™ ρίοηϋΓ11

38. 2-Allyloxy-2- (2,4'-chlorophenyl) -3- (imidazol-1-yl) propionitrile

39. 2-Ethoxy-2- (3,4-dichlorophenol) -3-4-imidazol-1-yl-proppooniril

40. 3- (imiddol-11-yl-2-eeyl-L-2-1,2,2-tri-methipropropoyl) -propionate, hydronitrate

41. 3- (Imidazol-1-yl) -2- ₍ 4-chloro-ethyl) 2-phenolPP10 -inirril _f hydro-hydrate

42. 2- (2,2-Dimethylpropanol) -3- (imidasPl1-yl) -

2-EEI / _{lprroPiPit.rrl>} hydronnirát

43. 2- (-, 2-Amino-1-propyl-3-imidazole)

1-yl) -2-phenylpropionitrile

44. 2- (2-eiúorfenyl) -3- (imidazol-1-yl) _{-2pгopppyppopioιpitrri>} hydronntrát

45. 2-bmto: [eta] &lt; 2 &gt; -2- (2-fluorophenyl) -3- (imidazolyl);

46. 2- (4-Ephorophen-3-yl) -3- (imidazoo-1-yl) -2-propopyyrrpPooitrile

47. 2-Butoxy-2- (4-fluorophenyl) -3- (imidazol-1-yl) -propi] Piitrl hydronhydrate

48. 2-allyl-2- (2-fluprfluoro-L) -4- (imidazol-1-yl) -prop Poonirri, hydro-nitrate

49. 2-ethoxyl-2- (- fluorophenУ) -3- (Pmidazol-

(1-yl) -1- (1-yl) hydrate

50. 2- (2-Fluorophen-1-yl) -3- (L-dazcrt-1-yl) -2-methopyypppipipitrri, hydrate

5. 3- (illdaaoP-11-L-fei-L-2- (1, -, - trlmeethl-ppopppy) ^ - poppppitгrl

52. 2- (2-Fluoro-enyl) -3- (imideaoo-1-yl) - 2pгppppypprppρpitгPl

53. 2-but Piqy 2- (2-fluorophenyl) -3- (imidazol-1-yl) propionic acid

54. 2- (ЗfluorfeiyУ) -3- (imlaιaoPL-1-1) -2pгopppyyprpPopitrPl

55. 2-b-toix-2- (4 - (-) -) -

(1-yl) -propylpyridine

56. 2-12-Eluorophenyl) -3- (LmPdazol-1-yl) -2-methoxyprPpPpnP trPi

57. 2-Ethoxy-2- (2-fluorophenyl) -3-imide. zol-1-yl) -prpPPnitgP1

58. 2-Allylphenyl-2- (2-amino-L-3- (imidaool-1-yl) -propplopiamine)

59. 2-Allyloxy-2- (4-fluorophenyl) -3- (imidazol-1-yl) -1-piperidin-1-hydrate

60. 2-ethoxy-22-fluoro-phenyl) -3- (imida zoo-1-yl) -ppppPLolirri, hydrpo nitrate

61. 2- (4-Fluoro-phenyl) -3- (imdaquinoo-1-yl) -2-methoxyproponitrile, hydronate

Second eehooy 2- 2- ((-feloofennn} -33 ((MLDA FPO-1-yl) -propipontrll ° * n - n 0 1,550 ° £ «· ¹ 538 1 n £ ° = ^1, 553" 1 n ° * ^«1, 537 2

mp: 168-173 ° C (dec.)

mp: 158-160 ° C (decomposition)

mp: 168-171 ° C (dec.)

mp: 89-91 ° C

mp: 170-172 ° C (decomposition)

mp: 173-176 ° C (dec.)

mp: 150-152 ° C (decomposition)

mp: 162-165 ° C (decomposition)

mp: 169-171 ° C (dec.)

mp: 172-175 ° C (decomposition)

mp: 177-179 ° C (dec.)

^t . ^t . 113 to 1 n ⁴ ° ⁿ £ with ¹ , 5'4 3 ni ° ⁿ D with 1,510 8 n £ ° ⁿ £ _ я 1 ^, 511 5 к 1 ^, 508 n £ ° » 1 ^, 528 '40 ⁿ D 3 1,518 7 _n D ^N ° 4 3 1 ^, 528 8

mp: 159-161 ° C (decomposition)

mp: 182-184 ° C (decomposition)

t. 194-196 ° C (dec.)

mp: 54-57 ° C

Yield: 88 ° C

63. 2- (4-Fluoro-phenyl) -3- (imiddoo-1-yl) -2-methoxy-propionitrile

64. 2-lploxp-2- (4-fluorophenyl) -3- (imidazole-1-pl) -roopioniiril

5. 2-Decyloxy-3- (imidazoP-1-p1) -2-feyl-

- - - - - - - -

66. 2- (3 ', (1'-iodo-2-yl) -2-nitro-propenoic acid), Oydronitoate

67. 3- (imiddzoo-1-η 4 -) - octplox β 4 -phenoproylitrile

68. 2- (4-bromophenyl) -2-butPxp-3- (imidazoo-1-

-pl) -roppiopitrile _> Opddpoitrár

69. 2- (4-brnmfeypl) -3- (1-imiddzoo pl) _{-2-rrproзχφropronitril>} tydrpnitrár

70. 2- (4-brpmphylP) -2-0exylPxy-3- (imidaopl-1-pl) -ггррГшУ trii, OpadPoitoár

71. 3- (Imidazoo-1-yl) -2- (2-methylphenyl) -2-oxo-oxoic acid, Opdd

72..2-OexylpxypЗ- (imidazoP-1-pI) -2- (2-meth-tert-ethyl) -propen,

73. 2- (4-brpmt-1-yl) -2-burpχp-3- (imidazoP-1-pl) -roopipylidil

74. 2- (4-bromophenyl) -3- (imidazoP-1-p1) -2-propylpyrropippirril

75. 2- (4-Boronaphthyl) -2-OexylPxy-3- (imidazin-1-pl) -ro- ^β- ionilril

6. 2-Butoxo-3- (imidazol-1-yl) -2- (2-methylphenyl) -1-piperpropenyl

77. 2-butoxp-3- (lmiddao0 ·) 1-yl) -2- (2-methplfeyyl) -R ^г _opropУlril> Oydronitrár

78. 2-OexylPxy-3- (imiddaoP-1-II) -2- (2-methylphenyl) -4-oxyl

79. 2-Decyloxy-3'- (imiddaool-1-yl) -2-methyl-piperidin-1-yl

80. 3- (imidazol-1 -pl) -2- (2-meehopfeypl ') -2-rrpr0 ^{3 ¢} χpropronitril

81. 2-Butoxy-2- (3-chlorophenyl) -3- (imidazo-1-yl) -propropionyl

82. 2- (3-C0-chloropheyyl) -2-OexllPXl-3- (imidazl-4-yr)

83. 2-decllρχy-3- (lmidaao0-1-yl) -2- (2-merOplfeyyl) _{-rrθprioУlril>} Opddpyitoár

84.3- (imidazo-1-p)) - 2- (2-methoppheypi) -2-octyl xprmr ion i1

85. 2-Decyl-3- (imidazol-1-yl) -2- (2-methylphthyl) -propylpyrrolidone

86. 2-ButPxp-3- (4-methoxys-1-pl) -2- (4-methoxyl-4-methoxyl), Oydogonitrár

87. 2-ButPxp-3- (imiddzoP-1-II) -2- (4-methoxylphenyl) -propropionic.

88. 2- (4-cycloofel-2-yl) -2-oxo-oxo-3- (imidzool-1-ll) -roopronУl1, OpddPg

89. 2- (4-Hydroxyphenyl) -2-Oexyloxy-3- (imidazol-1-yl) -propylpropyl, γ-piperidin-1- ^yl -1 ^ 21 9

Year: 126 zž (moklzd)

Ť. y .: 195 zz

128

Mp 198 ° C

174 ° C yj ° «1.505 5 year: 171 (rpaklad)

Year: : 162 to 165 ° C (moklzd) Year: : 135 to 138 ° C (moklzd) ^r . ^r >< mp 180 to 183 ° C (moklzd) Year: : 170 to 173 ° C (moklzd) у £ ° · 1 ^, 540 5 y * ° - 1., 541 8 y £ ° - 1,527 4 ⁿ D ^- 1,524 8 Year: : 184 to 186 ° C 40 zD ' 1,516 3 40 ₃ W ' 1,502 0 40 zD ⁰ - 1,527 6 40 zD ⁰ - 1,528 2 Year: Mp 162-165 ° C

155 (wet) r. Yield: 151 ° C (wet) ° C i * ⁰ . - 1.517 3

Уд ⁰ * 1 ^, 516 9

year: 163 zž (moklzd)

167 ° C i * U - 1,522 8 year: 195 zz (rnaklzd)

year: 158 zž (moklzd)

197

Mp 163 ° C

It is possible to combine 3-amino-sulfo-oxyl-3-cyano-sulfonoyl-3-cyano-sulfonoyl-3-cyano-sulfonoyl-oxylic acid;

These arylaulfonyloxy or alkylsulfonyloxy compounds of formula (II) are obtained by methods known per se or known per se (cf. Rubin et al., For example). Jacs 67,192 f (1945) $ Hess et al., Berd Chem · Ges. 50, 394 (1917)) accessible to phenylacetonitriles of formula III

R-CH

CN wherein R and R 1 have the meaning given in formula I, hydroxymethylated according to known methods and the thus obtained 3-hydroxypropionitriles of formula IV

O-R «. AND

R-C-CH3-OH (IV)

CN, wherein R and R mají are as defined for formula I, are reacted with suitable sulfonic acid derivatives such as sulfonic acid chlorides, optionally with the addition of acid binders.

The known 3-halopropionitriles of the formula II with Y in the meaning of halogen are obtained by reaction of the aforementioned phenylacetonitriles of the formula III with dihalomethanes by methods known per se.

The production of the starting product is further described.

3-methylsulfonyl-2-phenyl-2-propoxypropionitrile

37 g (0.154 mol) of 2-phenyl-2-propoxyacetonitrile are dissolved in 120 ml of pyridine and 18.5 g (0.614 mol) of paraformaldehyde are added. 7.7 ml of tetrabutylammonium hydroxide (TBAOH) are added to this suspension while cooling with ice. The reaction mixture is poured onto ice water and extracted twice with ether. The ether phase is washed twice with aqueous sodium chloride solution and then concentrated with magnesium sulphate. After filtering off the drying agent and rotating in vacuo, a colorless oil remains, which is uniformly thin-layer chromatographically and can be further processed without further purification.

Yield: 28.4 g (90% of theory)

3-hydroxy-2-phenyl-2-propoxypropionitrile (0.136 mol) of 3-hydroxy-2-phenyl-2-propoxypropionitrile was dissolved in 200 ml of toluene and 19.5 g of methanesulfonic acid chloride was added. 18.6 g (0.184 mol) of triethylamine are added dropwise at Ю ° C. It is stirred for 30 minutes at room temperature, the precipitated triethylamine hydrochloride is filtered off and concentrated. The residue is taken up in ether, washed with dilute HCl solution, water and sodium bicarbonate solution and twice more with water.

It is dried over magnesium sulphate, the drying agent is filtered off with suction and concentrated. The oily residue is dried under vacuum. TLC is pure.

Yield: 32.27 g »86% of theory n _D = 1,500

3-methylaulfonyl-2-phenyl-2-propoxypropionitrile

The following examples serve to explain the possible uses of the compounds of the invention, which are in the form of the foregoing formulations.

Example 3

Effect of seed treatment against Helminthosporium spec · on barley ·

Barley seeds with natural pests of Helminthosporine gramineum were untreated or sown in pots as indicated in the table and allowed to germinate below +16 ° C. every test member counted with fungi infested plants ·

The ringicidal effect ae is calculated as follows:

100 · infections in the treated

100 - ———— - ^{1 1} «% of the attack effect in the untreated

Compounds used as 20% spray powder ·

Compound of the Invention Active ingredient%

100 kg of seed Effect 1 50 95.6 2 50 100 ALIGN! 3 50 100 ALIGN! 4 50 100 ALIGN! 5 50 100 ALIGN! 6 50 100 ALIGN! 7 50 100 ALIGN! 8 50 100 ALIGN! 9 50 100 ALIGN! 10 50 100 ALIGN! 11 50 100 ALIGN! 12 50 100 ALIGN! 13 50 · 100 ALIGN! 14 .50 100 ALIGN! 15 Dec 50 100 ALIGN! 16 50 100 ALIGN! 17 50 100 ALIGN! 18 50 100 ALIGN! 19 Dec 50 100 ALIGN! 20 May 50 100 ALIGN! 21 50 100 ALIGN! Comparative agent Methoxyethyl-Hg-silicate 2.63 87

Effect of prophylactic treatment of leaves against Erysiphe cichoraceerum on pumpkin plants in greenhouse ·

Young pumpkin plants sprayed with the indicated concentrations of active substance were inoculated by spraying with dry spores of powdery mildew of Erysiphe cichoracearum after incubation and incubated together with un-treated untreated control plants in a greenhouse at 24 ° C.

The fungicidal effect was calculated as follows:

100 · infections in the treated

100% of the effect of the attack in the untreated

The substances were prepared as 20% spray powder ·

Compound of the Invention Active substance concentration% tJíin.lc% 1 0,025 100 ALIGN! 0.005 100 ALIGN! 0.001 100 ALIGN! 2 0,025 100 ALIGN! 0.005 100 ALIGN! 0.001 100 ALIGN! 3 0,025 100 ALIGN! 0.005 100 ALIGN! 0.001 100 ALIGN! 4 0,025 100 ALIGN! 0.005 100 ALIGN! 0,001 -. 100 ALIGN! 5 0,025 100 ALIGN! 0.005 100 ALIGN! 0.001 100 ALIGN! 6 0,025 100 ALIGN! 0.005 100 ALIGN! 0.001 100 ALIGN! 7 0,025 100 ALIGN! 0.005 100 ALIGN! 0.001 100 ALIGN! 8 0,025 100 ALIGN! 0.005 100 ALIGN! 0.001 100 ALIGN! 9 0,025 100 ALIGN! 0.005 100 ALIGN! 0.001 100 ALIGN! 10 0,025 100 ALIGN! 0.005 100 ALIGN! 0.001 100 ALIGN! 11 0,025 100 ALIGN! 0.005 100 ALIGN! 0.001 100 ALIGN! 12 0,025 100 ALIGN! 0.005 100 ALIGN!

The compound of the invention no. Active substance concentration% Effect % 12 0.001 100 ALIGN! 13 0,025 100 ALIGN! 0.005 100 ALIGN! 0.001 100 ALIGN! 14 0,025 100 ALIGN! 0.005 100 ALIGN! 0.001 87 <5 0,025 100 ALIGN! 0.005 100 ALIGN! 0.001 100 ALIGN! 16 0,025 100 ALIGN! 0.005 100 ALIGN! 0.001 100 ALIGN! 17 0,025 100 ALIGN! 0.005 100 ALIGN! • 0.001 100 ALIGN! 18 0,025 100 ALIGN! 0.005 100 ALIGN! 0.001 100 ALIGN! 19 Dec 0,025 100 ALIGN! 0.005 100 ALIGN! 0.001 100 ALIGN! 20 May * 0.025 100 ALIGN! 0.005 100 ALIGN! 0.001 100 ALIGN! 21 0,025 * 100 ALIGN! 0.005 106 0.001 100 ALIGN! 22nd 0.001 100 ALIGN! 0.0002 100 ALIGN! 23 0.001 100 ALIGN! '- 0.0002 100 ALIGN! 24 0.001 100 ALIGN! 0.0002 100 ALIGN! 25 0.001 100 ALIGN! 0.0002 100 ALIGN! 26 0.001 100 ALIGN! 0,0002 ' 100 ALIGN! 27 Mar: 0.001 100 ALIGN! 0.0002 100 ALIGN! 28 0.001 100 ALIGN! 0.0002 100 ALIGN! 29 0.001 100 ALIGN! 0.0002, 100 ALIGN! 30 0.001 100 ALIGN! 0.0002 100 ALIGN! 3 » 0.001 100 ALIGN! 0.0002 100 ALIGN! 32. 0.001 100 ALIGN! 0.0002 - 100 ALIGN! 33 0.001 100 ALIGN! 0.0002 100 ALIGN!

The compound of the invention no. Active substance concentration% Effect% 34 0.001 100 ALIGN! 0.0002 100 ALIGN! 35 0.001 100 ALIGN! 0.0002 100 ALIGN! 36 0.001 100 ALIGN! 0.0002 98 37 0.001 100 ALIGN! 0.0002 100 ALIGN! 38 0.001 100 ALIGN! 0.0002 100 ALIGN! 39 0.001 100 ALIGN! 0.0002 100 ALIGN! 40 0.001 100 ALIGN! 0.0002 100 ALIGN! 41 0.001 100 ALIGN! 0.0002 100 ALIGN! 42 0.001 100 ALIGN! 0.0002 100 ALIGN! 43 0.001 100 ALIGN! 0.0002 100 ALIGN! 44 0.001 100 ALIGN! 0.0002 100 ALIGN! 45 0.001 100 ALIGN! 0.0002 100 ALIGN! 46 0.001 100 ALIGN! 0.0002 100 ALIGN! 47 0.001 100 ALIGN! 0.0002 100 ALIGN! 48 0.001 100 ALIGN! 0.0002 100 ALIGN! 49 0.001 100 ALIGN! 0.0002 ÍOO 50 0.001 100 ALIGN! 0.0002 100 ALIGN! 51 0.001 100 ALIGN! 0.0002 100 ALIGN! 52 0.001 100 ALIGN! 0.0002 100 ALIGN! 53 0.001 100 ALIGN! 0.0002 100 ALIGN! 54 0.001 100 ALIGN! 0.0002 100 ALIGN! 55 0.001 100 ALIGN! 0.0002 100 ALIGN! 56 0.001 100 ALIGN! 0.0002 100 ALIGN! 57 0.001 100 ALIGN! 0.00002 100 ALIGN! 58 0.001 100 ALIGN! 0.0002 100 ALIGN! 59 0.001 100 ALIGN! 0.0002 100 ALIGN!

Compound of the Invention Active substance concentration% Effect % 60 0.001 100 ALIGN! 0.0002 100 ALIGN! 61 0.001 100 ALIGN! 0.0002 100 ALIGN! 62 0.001 100 ALIGN! 0.0002 100 ALIGN! 63 0.001 100 ALIGN! 0.0002 100 ALIGN! 64 0.001 100 ALIGN! 0.0002 100 ALIGN! 65 0,0025 100 ALIGN! 0.00025 100 ALIGN! 66 0,0025 100 ALIGN! 0.00025 100 ALIGN! 67 0,0025 1 oc 0.00025 100 ALIGN! 68 0,0025 100 ALIGN! 0.00025 100 ALIGN! 69 0,0025 »00 0.00025 i 00 70 0,0025 100 ALIGN! 0.00025 100 ALIGN! 71 0,0025 100 ALIGN! 0.00025 100 ALIGN! 72 0,0025 100 ALIGN! 0.00025 100 ALIGN! 73 0,0025 100 ALIGN! 0.00025 100 ALIGN! 74 0,0025 100 ALIGN! 0.00025 100 ALIGN! 75 0.0005 99 * 0.00005 100 ALIGN! 76 0.0005 100 ALIGN! 0.00005 100 ALIGN!

Example · 5

Effect of leaf treatment against Piricularia oryzae on rice seedlings in greenhouse ·

Young rice plants were sprayed with the active ingredients listed in the table.

After the spray had dried, the treated plants as well as the untreated cultured plants were treated with a spray. plants inoculated with a spore suspension (about 200,000 per m.) of liso skvxriicoti agent Piricdlsria oryzae and moist incubated in a greenhouse at +25 to +27 ° C «

After 5 days, the percentage of leaf area bio attacked was determined.

Ιό

100 · infections in the treated

100 - ——— ------— - as% attack effect in untreated

The substances were prepared as a 20% spray powder.

The compound of the invention no.

2a

Active substance concentration%

OJ

0.02

0.1

0.02

0.1

0.02

0.1

0.02

0.1

0.02

0.1

0.02

0.1

0.02 ° S

0.02

0.1

0.02

0.1

0.02

OJ

0,02 ''

0.1

0.02

0.1

0.02

0.1

0.02

0.1

0.02

Effect%

97.3

94.5

77.5

92.5

97.5

92.5

Example 6

Effect of prophylactic treatment of leaves against Botrytis cenerea on tomato plants in greenhouses.

Young tomato plants were sprayed with the active ingredient concentration given in the table *. After the spray had dried, the treated plants as well as the untreated plants were inoculated with a spore suspension (about 1 million per ml of fruit juice solution) of Botrytis cinerea and incubated moist in a greenhouse at about 20 ° C. After the collapse of the untreated plants (100% attack), the degree of infestation of the treated was determined. the lungicidal effect was calculated as follows:

100 · infections in the treated

100 ---% effect of infestation in untreated

The compounds of the invention were used as 20% preparations.

Compound of the Invention Concentration effective % Effect % 2 0,025 95 3 0,025 80 12 0,025 90 13 0,025 95 14 · 0,025 60 15 Dec 0,025 85 16 0,025 70 17 0,025 90 18 0,025 90 19 Dec 0,025 95 20 May 0,025 90 21 0,025 · 80

Comparative experiment

1- (4-difluorophenoxy) -3' _- 3'-dimethyl-1- (1,2,4-triazol-1-yl) -2-butanone 0.025

Example 7

Effect of prophylactic treatment of Plasmapara viticola leaves on vine plants in greenhouse. ;

Young vine plants with about 5 to 8 leaves were sprayed with said konccnttaci after zasetautí spraying moistened · spore suspension on spotaí side sheets (about 20,000 to and ^IH Ned were incubated in the 'greenhouse at ^22-2 4 ° C with ^p hen possible with water · steam saturated atmosphere ·

From the next day the air humidity was reduced to a normal level for 3-4 days (30 to 70% · saturation) and was then swelled for one day to saturate the vapors. The treatment was calculated as follows to determine the fungicidal effect:

100 · infections in the treated

100 - ....... - ---——--——— =% attack effect in untreated

Tulle substance · prepared as 20% spray powder ·

The compound of the invention no. Concentration of active substance% Effect% 11 0,025 89 12 0,025 93,3, 13 0,025 92.5 14 0,025 73 15 Dec 0,025 95.4 16 0,025 82 17 0,025 92.7 18 0,025 94.6 19 Dec 0,025 . 95.5 20 May 0,025 65

236490

Compound of Invention S. Active substance concentration% Effect% 21 0,025 81

Example 8

Watercress seeds were treated in the laboratory with an aqueous emulsion of the composition of the invention. The concentration of the active ingredient in the emulsion was 100 ppm. A glass slide was placed in a 200 ml glass cylinder with 10 µl of the active substance emulsion for this purpose. The slide paper was coated with fusion paper. When the paper was moistened with the solution, 10 watercress seeds were evenly distributed over the paper. The lid of the Petri dish was then placed on the cylinder. Two glass cylinders were prepared for each substance.

The shoots and roots were measured for germinated seeds after 7 days for evaluation.

The table shows the values in relation to the review and the percentages.

The compounds of the invention have been shown to exert a strong effect on the growth of shoots and roots in watercress.

Compound by Increase in%

of the invention no. Sprout Root 1 71 57 2 86 71 3 67 100 ALIGN! 4 67 57 5 67 43 6 67 71 7 83 86 8 67 71 9 67 71 10 83 71 11 100 ALIGN! 67 12 ' 50 22nd 13 50 22nd 14 100 ALIGN! 78 15 Dec 67 44 16 50 44 17 83 56 18 67 67 19 Dec 100 ALIGN! 56 20 May 83 78 21 50 44 22nd 50 57

Example 9

Cotton was grown to the loop stage under greenhouse conditions. The compounds of the invention were sprayed on the plants at a rate of 1 and 2 kg of active compound / ha. Three weeks after administration, the total length of rossiin and the length of the first internas were measured. The table shows the results in the form of percentages as a comparison to the control.

It shows a reduction in growth, which is generally stronger than that of the comparator.

Compound of the Invention Active substance kg / ha Total plant length in% Length of nodium 1 11 1 75 32 2 46 9 12 1 83 60 2 59 19 Dec 13 1 69 34 2 37 4 14 1 82 57 2 65 42 15 Dec 1 83 66 2 60 42 16 1 87 66 2 69 42 ¹⁷ 1 60 32 2 41 9 18 1 69 15 Dec 2 52 13 19 Dec 1 48 15 Dec 2 45 9 20 May 1 75 43 2 52 9 21 1 95 72 2 71 34 22nd 1 100 ALIGN! 70 2 55 62 Comparative means 2-chloroethyltrimethyl- ammonium or i d 1 52 23 2 44 23

He did

Effect of treatment of seeds against powdery mildew on Erysiphe graminis on barley ·

Summer barley seed was untreated or pickled Ю0 g of active substance / 100 kg sown in soil in pots and left at 20 ° C in the greenhouse for germination. areas covered with powdery mildew ·

The fungicidal effect was calculated as follows:

100 · infections in the treated

100 - i - · —i .. · -% attack effect of untreated

23648U

Possible intolerance of the treatment was assessed after emergence of the plants ·

The evaluation was carried out according to the scheme = complete destruction = 90% destruction * 60% destruction »70% destruction = 60% destruction = 50% destruction ж 40% destruction = 30% destruction and 20% destruction = Ю% roar = undamaged

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

In contrast to the comparative composition, the compounds according to the invention not only show full activity against Erysiphe graminis, but also are fully tolerant to barley.

The compound of the invention no. Effect% Tolerance 1 100 ALIGN! 10 2 100 ALIGN! 10 5 100 ALIGN! 10 6 100 ALIGN! 10 7 100 ALIGN! 10 8 100 ALIGN! 10 9 99.5 10 10 100 ALIGN! 10 11 93 10 15 Dec 100 ALIGN! 10 16 99 10 17 95 Ю 21 100 ALIGN! 10 22nd 100 ALIGN! 10 Comparative means 1- (4-Chlorophenoxy) -3,3-dimethyl-+ - (1,2,4-triazol-1-yl) -2-butanone 100 ALIGN! 4

Example 11

Effect of prophylactic treatment of leaves against blight (Cercospora beticola) on diabetes (Beta vulgaris).

Sugar plants with 4 well developed leaves were sprayed with the indicated concentrations. After spraying had dried, the treated plants and the untreated control plants were uniformly moistened with a suspension of 15,000 spores of Cercospora per ml. Deň: 32 ° C. The proportion of infested leaf area was then recorded. The effect of fungicides was calculated as follows!

, 100. infections in treated »% Effect infestation in untreated Compound by le Concentration effective effect of Invention no. substances in% % 1 0.09 100 ALIGN! 0.01 100 ALIGN! 2 0.05 100 ALIGN! 0.01 100 ALIGN! 4 0.05 100 ALIGN! 0.01 99 5 0.05 100 ALIGN! 0.01 96 11 0.05 100 ALIGN! 0.01 100 ALIGN! 12 0.05 100 ALIGN! 0.01 99.6 13 0.05 100 ALIGN! 0.01 93 14 0.05 100 ALIGN! 0.01 99.6 15 Dec 0.05 100 ALIGN! 0.01 98 17 0.05 100 ALIGN! 0.01 99 18 0.05 100 ALIGN! 0.01 99.6 19 Dec 0.05 100 ALIGN! 0.01 99.3 20 May 0.05 100 ALIGN! 0.01 98 21 0.09 100 ALIGN! 0.01 99.6 Comparative means  _ '·' MananlehyУlelbis ^ 0.05 100 ALIGN! dithiocarbamat 0.01 79

Example 12

Suppression of fungal growth on a yellow solution.

In a 100 ml glass flask was added 20 ml of 1: 1 grape juice and water nutrient solution, and the tulle powder was added. Then it was. vaccinated with conidia. (sporam.) PanclclUm dLgltaUm. After 5 days at 22-24 ° C, the development of fungi on the surface of the nutrient solution was assessed.

No fungal growth, 1 * on the surface of a single-colony fungal colony, 5 to 10% of the surface area of the fungus stand 10 to 30% of the surface area covered with the fungus stand. 30 to 60% of the surface. covered with mushroom

5. and 60 to 100% of the surface covered by the fungus

The active ingredients, the concentration of the active ingredient in the nutrient solution and the results are shown in the following table.

Compound of the Invention Active substance concentration in nutrient solution% Development of fungi 5 0.0005 4 0.001 0 6 0.0005 4 0.001 1 17 0.0005 0 0.001 0 20 May 0.0005 0 0.001 0 21 0.0005 2 0.001 0 23 0.0005 0 0.001 0 24 0.0005 1 0.001 0 27 Mar: 0.0005 0 0.001 0 28 0.0005 0 0.001 0 29 0.0005 0 0.001 0 31 0.0005 0 0.001 0 32 0.0005 0 0.001 0 34 0.0005 0 0.001 0 37 0.0005 0 0.001 0 38 0.0005 0 0.001 0 Comparative means (according to DOS 26 04 047) 3- (imidazol-1-yl) -2-phenyl- 2-butylpropionitrile, 0.0005 5 hydronitrate 0.001 4

Untreated Nutrient Solution Control

Example 13

Effect of prophylactic treatment of powdery mildew on Uncinula nacator

Young grapevines of Silvana and aei 8 to Ю leaves were sprayed with the concentrations shown in the table. powdery mildew and fungicidal activity were calculated as follows:

attack in the treated

100 ------------------- ж% effect of infestation in untreated

In the untreated, the infestation reached 88.3% · The compositions were used as 20% spray powder The effects are shown in the table.

The compound of the invention no. % Effect against Uncinula necator s 0.025% 0.005% active ingredient 2 93 85 3 100 ALIGN! 100 ALIGN! 4 100 ALIGN! Ю0 5 100 ALIGN! 100 ALIGN! 6 / 100 99 7 100 ALIGN! 89 8 100 ALIGN! 95 9 87 63 10 100 ALIGN! 49 11 100 ALIGN! 100 ALIGN! 12 100 ALIGN! 63 13 100 ALIGN! 95 14 66 43 15 Dec 100 ALIGN! 100 ALIGN! 16 99 89 17 100 ALIGN! 100 ALIGN! 18 86 80 19 Dec 100 ALIGN! 89 20 May 93 86 21. 100 ALIGN! 100 ALIGN! 22nd 100 ALIGN! 92

Example 14

Effect of prophylactic treatment of leaves against scab of Venturia inaegualis in the wild. The shoots of apple trees of the MM106 species found in growth were treated with drops of the active substance of 0.1% concentration. After the spray had dried, a conidiospore suspension (330,000 per milliliter) was sprayed on the leaves and then the shoots were left for 3 days in the half-hour with fungal infection after covering with polyethylene bags. The bags were then removed. • After a total of 2 1/2 weeks of experiment duration, the proportion of area affected by scab was estimated as a percentage. The untreated control showed 99% attack. The effect of the treatment was calculated

as follows) infections in treated .100 100 - a% effect _ infestation in untreated

The compounds were in the form of 20% spray powder.

The compound of the invention no.

Effect%

100 ALIGN!

Example 15

Effect of leaves treatment against scab of apple Venturia inaequalis in the wild.

Apple plant sprouts found in MM 106 growth were sprayed with a conidiospore suspension (330,000 per milliliter) and kept immediately overlapped with polyethylene bags to keep them moist. The bags were removed after 3 days · Seven days after inoculation, the plants were sprayed with 0.1% concentration of the active substance · After a further 1 1/2 week the percentage of leaf area of the infected apple scab was estimated as percentage The compounds of the invention were as a 20% spray powder. The effect of the treatment was calculated as follows:

infections in treated. 100 ALIGN!

100 - —————— and% effect of infestation in untreated

Compound of the Invention

Efficiency%

Comparative means

2-butyl-3- (imidazol-yl) -2-phenylpropionitrile, hydronitrate

Example

Prophylactic

100 ALIGN!

100 leaves treatment against large Erysiphe graminis on barley ·

Plants with active ingredient listed (0.05%) · After the barley had dried in the first leaf stage, concentrations were sprayed with the addition of alkaryl polyglycol ether as wetting agent, these plants as well as untreated control plants were uniformly coated with grain plants infected with powdery mildew and incubated at 20 to 20 22 ° C, then average powdery mildew infestation was recorded for each pot (18-20 plants). The fungicidal effect was calculated according to the formula:

100 · sorting in the treated

100 - ........- .......-% effect of infestation in untreated

The substances according to the invention were as 20% formulations ·

Compound by% Effect p

Invention No · 0.025% active ingredient 0.005% active ingredient 3 100 ALIGN! 100 ALIGN! 4 100 ALIGN! 100 ALIGN! 5 100 ALIGN! 100 ALIGN! 6 100 ALIGN! 100 ALIGN! 7 100 ALIGN! 100 ALIGN! 8 100 ALIGN! 100 ALIGN! 9 100 ALIGN! 92 10 92 90 11 100 ALIGN! 100 ALIGN! 12 100 ALIGN! 100 ALIGN!

Severography, n

Price 2,40 Kčs

The compound of the invention no. % Effect p 0.025% active ingredient 0.005% active ingredient 13 100 ALIGN! 100 ALIGN! 14 100 ALIGN! 100 ALIGN! 15 Dec 100 ALIGN! 100 ALIGN! 16 100 ALIGN! 100 ALIGN! 17 100 ALIGN! 100 ALIGN! 18 100 ALIGN! 100 ALIGN! 19 Dec 100 ALIGN! 100 ALIGN! 20 May 100 ALIGN! 100 ALIGN! 21 100 ALIGN! 100 ALIGN! 22nd 100 ALIGN! 100 ALIGN!

Example 17

Effect of erythrocytic treatment of leaves against omyces aipenilculttut (bean rust) in the greenhouse.

RosHni bean bushes at the stage of developed primary leaves were sprayed with the active substance o ^^ βη ^ Βο! - 100 ppm. After the pate, the treated plants were treated as well as the 1 treated control, moistened with the urelo-spore suspension.

For two days, the plants were incubated in a humidifying cabinet at 22 ° C and then left under greenhouse conditions at about 22 ° C. 11 days after sputtering, rust pimples were counted (mean 253 per Ust in the untreated coronol). Funicilhí effect has been calculated usLedo:

pimples in treated. 100 ALIGN!

100 - ———————————————————————————————————————————————————————————————————————————————————————————————————————————————————————————————————————————————————————————?

The substances according to the invention were as 20% formulations and showed an effect of 90%,

Compound of the Invention Effect% 1 2 3 4 12 15 Dec 16 17 18 19 Dec 21. 22nd 27 Mar: 28 91 96 95 94 100 ALIGN! 99.5 95 99.4 99.9 98 ^, 6 95 95 97

Example 18

The effect of prlfllattCcke treatment of leaves against Helminthosporljm tem («Руг ^^ Ною © tres), brown barley aquire ·

Madé barley plants at the first leaf stage. were sprayed with the indicated concentrations. After the spray, the treated plants and untreated plants moistening sánpenzí conidiospores Helminthosporuum teres and zavlhčovací chamber cultured for 2 days at ^20-22 ° C _e p ^a week ^per ° ^C were recorded forging percentage of diseased leaf area. The fugicidal effect was calculated as follows:

infections in treated. 100 infections in untreated =% effect

The compounds were as 20% preparations. Compound of % Effect of the invention no. 500 ppm 100 ALIGN! 35 90 90 36 95 90 37 95 90 38 95 90 39 ' 95 95 40 100 ALIGN! 100 ALIGN! 41 100 ALIGN! 98 42 100 ALIGN! 100 ALIGN! 43 ' 100 ALIGN! 100 ALIGN! 44 100 ALIGN! 100 ALIGN! 46 100 ALIGN! 100 ALIGN! 47 100 ALIGN! 100 ALIGN! 48 100 ALIGN! 89 49 100 ALIGN! 100 ALIGN! 50 100 ALIGN! 96 51 100 ALIGN! 100 ALIGN! 52 100 ALIGN! 100 ALIGN! 53 96 96 54 100 ALIGN! 100 ALIGN! 56 100 ALIGN! 100 ALIGN! 57 100 ALIGN! 96 58 100 ALIGN! 89

Example 19

Effect of prophylactic treatment:! leaves against rust of Piucinia 'hordei on barley in air conditioned growth chamber.

Madé barley plants at the first leaf stage were sprayed with the mentioned concennraai. After the spray were treated 'plants and untreated control plants were infected tHnami overcoating ^ ^ nco rust-network and put in a growth ^{y é} komoorr. ^The plants were cultivated for 10 days at almost saturated air humidity at both ¹⁵ ° C and ¹⁵ ° C. The percentage of leaf area affected by rust was then recorded. The fungicidal effect was calculated as follows:

assault in. treated. 100 ALIGN!

100 - ...... ¹ '————— with% attack effect in untreated

The compounds were as 20% preparations

The table shows the good to very good effect of the numerous compounds of the invention

The compound of the invention no. Effect% 500 ppm 32 42 43 45 46 47 48 49 53 54 57 61 63 64 65 66 69 70 72 73 74 75 76 77 78 100 ALIGN! 100 ALIGN! 100 ALIGN! 100 ALIGN! 100 ALIGN! 100 ALIGN! 100 ALIGN! 100 ALIGN! 100 ALIGN! 100 ALIGN! 100 ALIGN! 100 ALIGN! 100 ALIGN! 100 ALIGN! 100 ALIGN! 100 ALIGN! 100 ALIGN! 100 ALIGN! 100 ALIGN! 100 ALIGN! 100 ALIGN! 100 ALIGN! 100 ALIGN! 100 ALIGN! 100 ALIGN!

Example 20

Effect of prophylactic treatment of leaves against rust of Puccinis striiformis on barley in an air-conditioned plant growth chamber.

Young barley plants in the first leaf stage were sprayed with the indicated concentrations. After spraying, both treated plants and untreated control plants were wetted with a Puccinia striiformis uredospore suspension of 1,1,2-trifluoro-1,2,2-trichloroethane and incubated in a growth chamber at 150 ° C. Deň: 32 ° C. In the first two days the air was almost saturated with moisture. After 15 days, the percentage of infected leaf area was recorded. The fungicidal effect is calculated as follows:

infections in treated · 100

The compound of the invention no. 100 - assault in the untreated 100 ppm - =% effect % Effect a 33 ppm 11 ppm 5 100 ALIGN! 12 100 ALIGN! 100 ALIGN! 100 ALIGN! 14 100 ALIGN! 15 Dec 100 ALIGN! 100 ALIGN! 100 ALIGN! 16 100 ALIGN! ¹⁷ \ 100 ALIGN! 100 ALIGN! 100 ALIGN! 18 100 ALIGN! 100 ALIGN! 93 28 100 ALIGN! 9β 78

23ο4Ωυ

Example 21

Effect of seed treatment against Helminthosporium sativum on barley in the plant climate chamber.

Barley seed with artificial infestation of Helminthosporium sativum was dusted with 50 g of active ingredient of the composition according to the invention per 100 kg. For each test member, 2 g of treated or untreated seed was sown in 6.5 x 6.5 cm plastic pots. Sand served as a substrate. Each experimental member was repeated 2 times. The pots were stored in a growth chamber at 15 ° C. After 4 weeks, the grown plants were examined for percent attack on the lower shoots. The fungicidal effect was calculated from the average of the repeats as follows:

infections in treated. 100 ALIGN!

--0 - ------—--------------— »% attack effect in untreated

The compositions of the invention were as 20% formulations.

The compound of the invention no.

% Effect against Helminthosporium sativum

99.5

100 ALIGN!

100 • 100

100 ALIGN!

100 ALIGN!

Comparative means

2-Butyl-3- (imidazol-1-yl) -2-phenylpropionitrile 98.5

2-Butyl-3- (imidazol-1-yl) -2-phenylpropionitrile, hydronitrate 98

Example 22

Effect against Pseudomonas phaaeolicola, a causative agent of bacteriosis beans, in vitro.

The malt agar was cooled to 45 ° C after heat sterilization and then mixed with the test substances in an aqueous preparation and poured into plastic petri dishes. After solidification of the broth, the agar-treated as well as untreated agar plates were inoculated in the middle with a suspension of the bacterium Pseudomonas phaseolicola. The plates were then incubated at 22 ° C. After 2 1/2 weeks, radial elongation was measured. grown colonies of bacteria. From the average of two replicates of each experimental member, the growth-inhibiting effect was calculated as follows:

radial growth in treated. 100 ALIGN!

100 - -----—- Radial Growth in Untreated Compounds were as 20% preparations.

=% inhibitory effect% Suppressive effect 250 ppm of the active ingredient in agar against Pseudomonas phaseolicola.

Severography, n. P., MOST

Price 2,40 Kčs

Compound of the Invention

'

Comparative • 2-butyl-3- (imidazol-1-yl) -2-phenylpropioitrile, hydrite

Example 23 effective ^ek profýlaktlckáh ⁰ ofctfefflí sheets against E ^ Pac SLPH gramiiiis aa jčrneni gk ^{e! e} Extruder, 'Young barley plants at leaf stage were sprayed with the specifications given concentrations. After the spray had dried, the treated plants as well as the untreated control plants were inoculated with dry savage plants by overwhelming the test plants with the infected plants. Then, the test plants were cultivated in a greenhouse at about 20-22 ° C and evaluated after a week for the percentage of leaf area attack. Fu ^ n ^ i <^ id ^ :(. The effect was calculated as follows:

infections in treated. 100 ALIGN!

100> - ————————— °% attack effect in untreated

The compounds were as 20% preparations.

The compound of the invention no. % Effect 100 ppm 20 ppm 28 100 ALIGN! 100 ALIGN! 29 1 OO 100 ALIGN! 30 100 ALIGN! 99 31 100 ALIGN! 100 ALIGN! 32 - 100 ALIGN! 33 100 ALIGN! 100 ALIGN! 34 100 ALIGN! 100 ALIGN! 35 100 ALIGN! 100 ALIGN! 36 100 ALIGN! 100 ALIGN! 37 100 ALIGN! 100 ALIGN! 38 * 100 ALIGN! 100 ALIGN! 39 / 98 90 40 100 ALIGN! 91 41 100 ALIGN! 100 ALIGN! 42 100 ALIGN! 100 ALIGN! 43 · 96 91 44 100 ALIGN! 100 ALIGN!

Compound of the Invention % Effect 100 ppm 20 ppm 45 100 ALIGN! 96 46 100 ALIGN! 100 ALIGN! 47 100 ALIGN! 100 ALIGN! 48 100 ALIGN! 100 ALIGN! 49 100 ALIGN! 100 ALIGN! 50 100 ALIGN! 100 ALIGN! 51 100 ALIGN! 100 ALIGN! 52 100 ALIGN! 100 ALIGN! 53 100 ALIGN! 100 ALIGN! 54 100 ALIGN! 100 ALIGN! 55 100 ALIGN! 100 ALIGN! 56 100 ALIGN! 100 ALIGN! 57 100 ALIGN! 87 58 100 ALIGN! 100 ALIGN! 59 100 ALIGN! 98 60 100 ALIGN! 100 ALIGN! 61 100 ALIGN! 100 ALIGN! 62 100 ALIGN! 100 ALIGN! 63 99 95 64 100 ALIGN! 100 ALIGN!

Claims (2)

A composition having fungicidal and bactericidal action, characterized in that in a mixture. . s - carriers. and / or the wetted substances as active ingredient are imidazolylprooPoittiles of the general formula I, R &lt; 2 &gt;. ¹ / = ¹ "-C CHa Nj CN (I) in which R is fenfl, halophenyl, dichlorophenyl, methphenyl or methophenyl, Rj is Cj to Cj _Q OLtyl, miyL or benzyl and their editorial. sooi with inorganic and organic acids. 2. A process for the preparation of a compound of formula (I) - as an active ingredient according to claim 1, characterized in that the compounds of formula (II) are reacted. O-R,. · [. RC-CH ₂ -O-SO ₂ -CH 3 (II); CN ... with an imidazole of formula III HC-NH HC CH Y (III), in thelolonootic solvent and optionally in theloonootic base, wherein in formula II R @ 1 R @ 1 is R @ 1 R @ 1 R @ 2; the aforementioned meaning.