NOVEL TRIAZOLE DERIVATIVES

Abstract

The present invention relates to novel triazole derivatives, to processes for preparing these compounds, to compositions comprising these compounds, and to the use thereof as biologically active compounds, especially for control of harmful microorganisms in crop protection and in the protection of materials and as plant growth regulators.

Claims

1. Triazole derivative of the formula (I) ##STR00007## wherein R.sup.1 represents substituted or non-substituted C.sub.1-C.sub.8-alkyl, wherein the substituents are selected from the group consisting of halogen, phenyl, phenoxy, halo-substituted phenoxy and halo-substituted phenyl; C.sub.2-C.sub.8-alkenyl; C.sub.2-C.sub.8-alkynyl; substituted or non-substituted C.sub.3-C.sub.7-cycloalkyl wherein the substituents are selected from the group consisting of C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl and halogen; R.sup.2 represents H or C.sub.1-C.sub.8-alkyl; R.sup.3 and R.sup.4 are identical or different and represent in each case hydrogen or C.sub.1-C.sub.8-alkyl; Y.sup.1, Y.sup.2 and Y.sup.3 independently represent hydrogen; halogen; C.sub.1-C.sub.8-alkyl or C.sub.1-C.sub.8-haloalkyl and at least one of Y.sup.1, Y.sup.2 and Y.sup.3 represents halogen; C.sub.1-C.sub.8-alkyl or C.sub.1-C.sub.8-haloalkyl; And/or an agrochemically active salts thereof, except for the compounds 2-(1-chlorocyclopropyl)-1-(3-chloropyridazin-4-yl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol 2-(1-chlorocyclopropyl)-1-(3,6-dichloropyridazin-4-yl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol 1-(3-chloropyridazin-4-yl)-2-(1-methylcyclopropyl)-3-(1H-1,2,4-triazol-1-yl)propan-2-ol.

2. Triazole derivatives of the formula (I) according to claim 1, ##STR00008## wherein R.sup.1 represents substituted or non-substituted C.sub.1-C.sub.8-alkyl, wherein the substituents are selected from the group consisting of halogen, phenyl, phenoxy, halo-substituted phenoxy and halo-substituted phenyl; C.sub.2-C.sub.8-alkenyl; C.sub.2-C.sub.8-alkynyl; substituted or non-substituted C.sub.3-C.sub.7-cycloalkyl wherein the substituents are selected from the group consisting of C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl and halogen; and R.sup.2 represents hydrogen or C.sub.1-C.sub.8-alkyl; and R.sup.3 and R.sup.4 are identical or different and represent in each case hydrogen or C.sub.1-C.sub.8-alkyl; and Y.sup.1, Y.sup.2 and Y.sup.3 represent independently hydrogen; halogen; C.sub.1-C.sub.8-alkyl or C.sub.1-C.sub.8-haloalkyl and at least one of Y.sup.1, Y.sup.2 and Y.sup.3 represents halogen; C.sub.1-C.sub.8-alkyl or C.sub.1-C.sub.8-haloalkyl; And/or an agrochemically active salt thereof, except for compounds of formula (I) wherein R.sup.1 represents a cyclopropyl substituted by chlorine or methyl in the 1-position and Y.sup.1 represents chlorine.

3. Triazole derivative of the formula (I) and/or salt according to claim 1, wherein R.sup.1 represents C.sub.1-C.sub.8-alkyl; halogen substituted C.sub.1-C.sub.8-alkyl; substituted or non-substituted C.sub.3-C.sub.7-cycloalkyl wherein the substituents are selected from the group consisting of C.sub.1-C.sub.4-alkyl, C.sub.1-C.sub.4-haloalkyl and halogen; R.sup.2 represents hydrogen or C.sub.1-C.sub.4-alkyl; R.sup.3 and R.sup.4 are identical or different and represent in each case hydrogen or C.sub.1-C.sub.4-alkyl; and Y.sup.1, Y.sup.2 and Y.sup.3 represent independently hydrogen; halogen; C.sub.1-C.sub.4-alkyl; C.sub.1-C.sub.4-haloalkyl and at least one of Y.sup.1, Y.sup.2 and Y.sup.3 represents halogen; C.sub.1-C.sub.4-alkyl or C.sub.1-C.sub.4-haloalkyl.

4. Triazole derivatives of the formula (I) and/or salt according to claim 1, wherein R.sup.1 represents C.sub.1-C.sub.4-alkyl; halogen substituted C.sub.1-C.sub.4-alkyl; substituted or non-substituted C.sub.3-C.sub.4-cycloalkyl wherein the substituents are selected from the group consisting of C.sub.1-C.sub.3-alkyl, C.sub.1-C.sub.3-haloalkyl and halogen; R.sup.2 represents hydrogen, methyl or ethyl; R.sup.3 and R.sup.4 are identical or different and represent in each case hydrogen or methyl; and Y.sup.1, Y.sup.2 and Y.sup.3 represent independently hydrogen; fluorine; chlorine; bromine; methyl; ethyl; i-propyl, tert-butyl; difluoromethyl; trifluoromethyl or pentafluoroethyl and at least one of Y.sup.1, Y.sup.2 and Y.sup.3 represents fluorine; chlorine; bromine; methyl; ethyl; i-propyl, tert-butyl; difluoromethyl; trifluoromethyl or pentafluoroethyl.

5. Triazole derivative of the formula (I) and/or salt according to claim 1, wherein R.sup.1 represents C.sub.1-C.sub.4-alkyl; chlorine or fluorine substituted C.sub.1-C.sub.4-alkyl; mono- or dihalophenyl substituted C.sub.1-C.sub.4-alkyl, wherein halo is selected from chloro and fluoro; R.sup.2 represents hydrogen; R.sup.3 and R.sup.4 represent hydrogen; and Y.sup.1, Y.sup.2 and Y.sup.3 represent independently hydrogen; chlorine; bromine; methyl; ethyl; difluoromethyl or trifluoromethyl and at least one of Y.sup.1, Y.sup.2 and Y.sup.3 represents chlorine; bromine; methyl; ethyl; difluoromethyl or trifluoromethyl.

6. Method for controlling harmful microorganisms in crop protection and/or in the protection of materials, comprising applying one or more compounds of the formula (I) and/or salts according to claim 1 to the harmful microorganisms and/or habitat thereof.

7. Method for controlling phytopathogenic harmful fungi in crop protection and in the protection of materials, comprising applying one or more compounds of the formula (I) and/or salts according to claim 1 to the phytopathogenic harmful fungi and/or habitat thereof.

8. Composition for controlling harmful microorganisms, optionally for controlling phytopathogenic harmful fungi, comprising a content of at least one compound of the formula (I) and/or salt according to claim 1, in addition to one or more extenders and/or surfactants.

9. Composition according to claim 8 comprising at least one further active ingredient selected from the group of the insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, fertilizers, safeners and semiochemicals.

10. A product comprising one or more compounds of the formula (I) and/or salts according to claim 1 for control of harmful microorganisms in crop protection and in the protection of materials, optionally phytopathogenic harmful fungi.

11. Process for producing a composition for controlling harmful microorganisms, optionally for controlling phytopathogenic harmful fungi, comprising mixing one or more compounds of the formula (I) and/or salts according to claim 1 with one or more extenders and/or surfactants.

12. A product comprising one or more compounds of the formula (I) and/or salts according to claim 1 for treatment of transgenic plants.

13. A product comprising one or more compounds of the formula (I) and/or salts according to claim 1 for treatment of seed.

Description

EXAMPLES

Preparation Examples

Preparation of Compounds of the Formula (I) According to Process A

Example 1a: Preparation of 1-(3-chloropyridazin-4-yl)-3,3-dimethyl-2-(1H-1,2,4-triazol-1-ylmethyl)butan-2-ol, compound I-713

[0242] ##STR00006##

[0243] Under argon 237.8 mg (1.79 mmol) 3-Chloro-4-methylpyridazine were dissolved under shirring and sonication (40 min) in 5.0 mL, dry tetrahydrofurane (THF) at 0° C. Under argon this solution was added to a mixture of 2.4 mL, (2.39 mmol) (2,2,6,6-Tetramethyl-1-piperidyl)magnesium chloride lithium chloride complex (1.0 M in THF/Toluene) dissolved in 3.0 mL dry THF at −70° C. The reaction mixture was stirred 15 min at −70° C. and then 250.0 mg (1.49 mmol) of 3,3-Dimethyl-1-(1H-1,2,4-triazol-1-yl)butan-2-one (for preparation see: G. Holmwood, Ger. Offen., 2937595, 1981) dissolved in 3.0 mL dry THF were added. After stirring 60 min at −70° C. and subsequently stirring at room temperature for 2.5 h, the reaction mixture was quenched by adding 5.0 mL of saturated aqueous NH.sub.4Cl solution at 0° C. After stirring for 15 min the mixture was diluted with ethylacetate and saturated aqueous NH.sub.4Cl solution. The phases were separated and the aqueous phase was extracted three times with ethyl acetate. The organic phases were combined and dried over MgSO.sub.4. The residue was purified by column chromatography over silica gel using dichloromethane/ethyl acetate (Gradient: 60/40 to 0/100). 66.7 mg (0.23 mmol, 15%) of the title compound were obtained.

[0244] The preferred and exemplary compounds according to the invention listed in Table 1 can be synthesized analogous to the above mentioned process.

[0245] For exemplary compounds according to the invention listed in Table 1 Log P values are given in Table 2 and NMR data are provided in Table 3.

TABLE-US-00002 TABLE 2 EX No R.sup.1 R.sup.2 R.sup.3 R.sup.4 Y.sup.1 Y.sup.2 Y.sup.3 LogP I-368 1-(4-chlorophenyl)-2-methylpropan-2-yl H H H chloro H H 2.75.sup.[a] I-441 1-ethylcyclopropyl H H H chloro H chloro 2.18.sup.[a] I-444 2,4-dichlorobenzyl H H H chloro H H 2.34.sup.[a] I-480 2,4-dichlorobenzyl H H H chloro H chloro 2.96.sup.[a] I-530 1,3-difluoro-2-methylpropan-2-yl H H H chloro H H 1.28.sup.[a] I-592 2-methylbut-3-en-2-yl H H H chloro H H 1.60.sup.[a] I-593 1-fluoro-2-methylpropan-2-yl H H H chloro H H 1.31.sup.[a] I-710 cyclopropyl H H H chloro H chloro 1.49.sup.[a] I-713 tert-butyl H H H chloro H H 1.48.sup.[a] I-745 1-ethylcyclopropyl H H H chloro H H 1.59.sup.[a] I-771 1-chloro-2-methylpropan-2-yl H H H chloro H H 1.70.sup.[a] I-799 cyclopropyl H H H chloro H H 0.84.sup.[a]

[0246] Measurement of Log P values for Table 2 was performed according to EEC directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on reversed phase columns with the following methods:

[0247] .sup.[a]Measurement of LC-MS was done at pH 2.7 with 0.1% formic acid in water and with acetonitrile (contains 0.1% formic acid) as eluent with a linear gradient from 10% acetonitrile to 95% acetonitrile.

[0248] Calibration was done with straight-chain alkan2-ones (with 3 to 16 carbon atoms) with known Log P values (measurement of Log P values using retention times with linear interpolation between successive alkanones). Lambda-max-values were determined using UV-spectra from 200 nm to 400 nm and the peak values of the chromatographic signals.

NMR-Peak Lists for Selected Compounds in Table 1

[0249] 1H-NMR data of selected examples are written in form of 1H-NMR-peak lists. To each signal peak are listed the δ-value in ppm and the signal intensity in round brackets. Between the δ-value-signal intensity pairs are semicolons as delimiters.

[0250] The peak list of an example has therefore the form:

δ.sub.1 (intensity.sub.1); δ.sub.2 (intensity.sub.2); . . . ; δ.sub.i (intensity.sub.i); δ.sub.n (intensity.sub.n)

[0251] Intensity of sharp signals correlates with the height of the signals in a printed example of a NMR spectrum in cm and shows the real relations of signal intensities. From broad signals several peaks or the middle of the signal and their relative intensity in comparison to the most intensive signal in the spectrum can be shown.

[0252] For calibrating chemical shift for 1H spectra, we use tetramethylsilane and/or the chemical shift of the solvent used, especially in the case of spectra measured in DMSO. Therefore in NMR peak lists, tetramethylsilane peak can occur but not necessarily.

[0253] The 1H-NMR peak lists are similar to classical 1H-NMR prints and contains therefore usually all peaks, which are listed at classical NMR-interpretation.

[0254] Additionally they can show like classical 1H-NMR prints signals of solvents, stereoisomers of the target compounds, which are also object of the invention, and/or peaks of impurities.

[0255] To show compound signals in the delta-range of solvents and/or water the usual peaks of solvents, for example peaks of DMSO in DMSO-D.sub.6 and the peak of water are shown in our 1H-NMR peak lists and have usually on average a high intensity.

[0256] The peaks of stereoisomers of the target compounds and/or peaks of impurities have usually on average a lower intensity than the peaks of target compounds (for example with a purity >90%).

[0257] Such stereoisomers and/or impurities can be typical for the specific preparation process. Therefore their peaks can help to recognize the reproduction of our preparation process via “side-products-fingerprints”.

[0258] An expert, who calculates the peaks of the target compounds with known methods (MestreC, ACD-simulation, but also with empirically evaluated expectation values) can isolate the peaks of the target compounds as needed optionally using additional intensity filters. This isolation would be similar to relevant peak picking at classical 1H-NMR interpretation.

[0259] Further details of NMR-data description with peak lists you find in the publication “Citation of NMR Peaklist Data within Patent Applications” of the Research Disclosure Database Number 564025.

TABLE-US-00003 TABLE 3 Example I-368: .sup.1H-NMR (300.2 MHz, d.sub.6-DMSO): δ = 9.254 (0.4); 9.238 (0.3); 9.186 (0.9); 9.168 (0.9); 9.006 (4.1); 8.989 (4.1); 8.576 (0.4); 8.498 (7.3); 8.349 (0.4); 7.966 (0.3); 7.824 (4.3); 7.807 (4.3); 7.784 (7.6); 7.755 (1.2); 7.738 (1.0); 7.381 (5.8); 7.354 (7.3); 7.282 (0.6); 7.212 (7.1); 7.184 (5.6); 7.099 (0.3); 5.781 (0.5); 5.386 (0.4); 5.252 (6.9); 4.611 (0.5); 4.593 (0.5); 4.551 (0.3); 4.530 (0.3); 4.477 (1.9); 4.428 (3.8); 4.368 (4.0); 4.320 (1.7); 4.065 (0.6); 4.043 (0.6); 3.423 (0.6); 3.342 (42.1); 3.306 (4.5); 3.232 (3.6); 3.185 (1.7); 3.127 (2.9); 2.898 (0.4); 2.881 (0.6); 2.795 (0.5); 2.690 (9.2); 2.525 (27.3); 2.405 (0.5); 2.064 (0.6); 2.012 (2.4); 1.530 (0.4); 1.491 (0.4); 1.469 (0.4); 1.420 (1.0); 1.326 (0.5); 1.261 (2.0); 1.222 (1.0); 1.198 (1.5); 1.163 (1.9); 1.093 (0.6); 1.071 (0.9); 1.038 (2.1); 1.014 (0.7); 0.969 (0.4); 0.949 (0.4); 0.810 (16.0); 0.765 (16.0); 0.689 (0.4); 0.678 (0.4); 0.602 (0.5); 0.023 (6.9) Example I-441: .sup.1H-NMR (300.2 MHz, d.sub.6-DMSO): δ = 8.357 (11.0); 7.952 (13.7); 7.943 (12.7); 5.779 (9.9); 4.852 (10.2); 4.604 (4.2); 4.556 (5.5); 4.288 (5.4); 4.240 (4.2); 3.532 (0.4); 3.480 (0.4); 3.416 (1.1); 3.348 (73.9); 3.198 (1.7); 3.150 (9.7); 3.138 (9.3); 3.091 (1.4); 2.525 (13.6); 2.012 (0.7); 1.956 (0.5); 1.932 (1.3); 1.909 (2.0); 1.886 (3.1); 1.861 (3.4); 1.830 (3.3); 1.805 (3.2); 1.781 (2.1); 1.759 (1.3); 1.258 (3.6); 1.222 (0.6); 1.197 (0.6); 1.173 (0.5); 0.878 (0.6); 0.831 (0.4); 0.707 (8.5); 0.682 (16.0); 0.657 (7.8); 0.211 (2.0); 0.191 (3.5); 0.153 (1.6); 0.070 (7.5); 0.052 (6.9); 0.023 (2.4); −0.069 (1.4); −0.106 (3.6); −0.126 (2.0) Example I-444: .sup.1H-NMR (300.2 MHz, d.sub.6-DMSO): δ = 9.133 (4.6); 9.116 (4.8); 8.438 (8.8); 8.028 (8.6); 7.906 (4.3); 7.889 (4.2); 7.647 (3.7); 7.619 (4.8); 7.602 (4.9); 7.595 (5.1); 7.443 (3.1); 7.436 (2.8); 7.415 (2.4); 7.408 (2.2); 5.780 (16.0); 5.414 (8.7); 4.346 (0.7); 4.298 (6.7); 4.292 (6.5); 4.243 (0.6); 3.411 (0.7); 3.345 (142.2); 2.977 (10.7); 2.952 (10.3); 2.530 (25.3); 2.525 (31.3); 2.519 (23.3); 1.259 (1.0); 0.023 (23.8) Example I-480: .sup.1H-NMR (300.2 MHz, CDCl.sub.3): δ = 8.210 (4.0); 8.037 (4.1); 7.695 (4.1); 7.448 (2.2); 7.441 (2.4); 7.357 (1.5); 7.329 (3.0); 7.300 (19.4); 7.282 (2.1); 7.275 (1.8); 7.255 (1.0); 7.248 (0.9); 5.339 (3.2); 4.324 (0.9); 4.277 (3.0); 4.239 (3.0); 4.193 (1.0); 4.172 (0.6); 4.148 (0.7); 3.011 (0.8); 3.001 (0.3); 2.964 (3.6); 2.953 (4.9); 2.950 (4.9); 2.938 (3.5); 2.891 (0.7); 2.084 (2.8); 2.047 (16.0); 1.981 (0.4); 1.941 (0.3); 1.928 (0.4); 1.907 (0.3); 1.819 (0.4); 1.774 (0.4); 1.759 (0.4); 1.702 (0.7); 1.684 (0.6); 1.670 (0.4); 1.475 (5.0); 1.322 (0.8); 1.298 (1.8); 1.274 (0.8); 0.107 (3.6); 0.038 (18.3); 0.027 (1.1) Example I-530: .sup.1H-NMR (300.2 MHz, d.sub.6-DMSO): δ = 8.984 (6.1); 8.967 (6.0); 8.369 (11.1); 7.778 (5.8); 7.761 (5.8); 7.738 (11.3); 5.781 (2.5); 5.628 (11.0); 4.689 (1.7); 4.657 (2.7); 4.637 (2.8); 4.601 (2.5); 4.570 (1.3); 4.546 (2.3); 4.530 (2.0); 4.513 (2.6); 4.499 (2.8); 4.478 (3.0); 4.440 (4.3); 4.390 (7.6); 4.357 (1.6); 4.325 (5.7); 4.276 (2.5); 3.483 (0.5); 3.419 (1.3); 3.352 (255.9); 3.281 (5.7); 3.185 (4.9); 3.137 (2.7); 2.656 (0.5); 2.623 (0.6); 2.525 (30.8); 2.012 (0.4); 1.286 (0.4); 1.260 (1.2); 1.198 (0.3); 1.176 (0.4); 1.162 (0.4); 1.008 (0.5); 0.957 (16.0); 0.851 (0.4); 0.023 (5.4); −0.041 (1.3) Example I-592: .sup.1H-NMR (300.2 MHz, CDCl.sub.3): δ = 8.972 (3.4); 8.955 (3.5); 7.983 (5.6); 7.819 (5.9); 7.679 (2.8); 7.662 (2.7); 7.300 (10.9); 6.075 (1.6); 6.041 (0.9); 6.037 (1.0); 6.019 (1.1); 6.014 (1.1); 5.980 (1.9); 5.121 (7.3); 5.086 (2.2); 5.083 (2.5); 5.064 (2.3); 5.061 (2.0); 4.729 (4.5); 4.727 (4.5); 4.473 (2.4); 4.426 (3.0); 4.030 (3.4); 3.982 (2.8); 3.275 (1.5); 3.228 (2.8); 3.135 (3.1); 3.088 (1.6); 1.642 (5.1); 1.170 (15.9); 1.119 (16.0); 0.105 (4.0); 0.047 (0.4); 0.036 (10.2); 0.025 (0.4) Example I-593: .sup.1H-NMR (300.2 MHz, d.sub.6-DMSO): δ = 8.981 (5.1); 8.964 (5.2); 8.442 (0.4); 8.397 (9.5); 7.785 (4.9); 7.768 (4.8); 7.739 (9.3); 5.535 (0.6); 5.349 (9.4); 4.631 (0.4); 4.507 (1.1); 4.475 (3.2); 4.448 (2.9); 4.416 (1.2); 4.393 (2.2); 4.344 (5.9); 4.316 (3.3); 4.288 (8.0); 4.256 (1.3); 4.239 (2.1); 3.445 (0.3); 3.340 (92.1); 3.285 (2.7); 3.237 (4.8); 3.145 (4.4); 3.096 (2.3); 2.530 (12.9); 2.524 (15.7); 2.406 (0.9); 1.411 (0.5); 1.327 (0.4); 1.259 (0.8); 1.238 (1.5); 1.233 (1.4); 1.190 (0.6); 1.158 (0.6); 1.096 (0.5); 0.982 (16.0); 0.978 (15.4); 0.956 (15.6); 0.950 (14.6); 0.023 (3.2) Example I-710: .sup.1H-NMR (300.2 MHz, CDCl.sub.3): δ = 8.206 (5.3); 8.049 (5.4); 7.691 (5.6); 7.300 (7.6); 5.337 (16.0); 4.427 (1.8); 4.381 (3.7); 4.296 (3.8); 4.249 (1.9); 4.169 (0.9); 4.145 (0.9); 3.940 (4.4); 3.180 (2.2); 3.135 (3.2); 2.928 (2.9); 2.883 (2.1); 2.208 (4.8); 2.081 (4.1); 1.640 (3.2); 1.319 (1.1); 1.295 (2.2); 1.280 (0.3); 1.271 (1.1); 0.893 (0.7); 0.883 (0.7); 0.875 (0.5); 0.865 (1.4); 0.856 (0.5); 0.848 (0.8); 0.838 (0.8); 0.820 (0.4); 0.256 (0.8); 0.244 (0.8); 0.237 (0.8); 0.227 (1.2); 0.216 (0.6); 0.209 (1.2); 0.198 (1.2); 0.180 (1.0); 0.166 (0.9); 0.152 (0.8); 0.122 (0.4); 0.104 (1.4); 0.090 (0.4); 0.084 (0.7); 0.069 (0.8); 0.057 (0.7); 0.052 (1.1); 0.035 (7.4); 0.024 (0.7); −0.028 (0.6); −0.040 (0.6); −0.045 (1.0); −0.057 (1.2); −0.063 (0.6); −0.075 (1.0); −0.090 (0.6) Example I-713: .sup.1H-NMR (300.2 MHz, d.sub.6-DMSO): δ = 8.977 (1.3); 8.964 (1.3); 8.428 (1.9); 7.778 (1.6); 7.765 (1.7); 7.739 (2.0); 5.073 (1.9); 4.359 (0.7); 4.311 (1.5); 4.258 (1.5); 4.209 (0.6); 3.367 (5.7); 3.230 (0.8); 3.183 (1.3); 3.097 (1.3); 3.050 (0.7); 2.528 (0.8); 0.958 (16.0) Example I-745: .sup.1H-NMR (499.9 MHz, CDCl.sub.3): δ = 9.033 (0.4); 9.028 (5.2); 9.018 (5.3); 8.149 (0.3); 8.112 (8.2); 7.949 (8.2); 7.682 (4.5); 7.671 (4.4); 7.261 (26.6); 5.058 (0.9); 4.647 (3.8); 4.619 (4.2); 4.245 (5.3); 4.242 (5.6); 3.943 (4.2); 3.915 (3.9); 3.297 (2.2); 3.295 (2.3); 3.269 (2.7); 3.267 (2.8); 3.132 (0.7); 3.020 (4.1); 2.992 (3.4); 2.434 (0.5); 1.887 (0.4); 1.872 (1.3); 1.857 (1.5); 1.844 (1.8); 1.829 (1.7); 1.814 (0.6); 1.751 (0.3); 1.680 (0.5); 1.665 (1.6); 1.651 (1.9); 1.637 (1.5); 1.623 (1.3); 1.608 (0.5); 1.567 (19.0); 1.354 (0.4); 1.348 (0.4); 1.256 (0.9); 1.050 (0.4); 1.035 (0.8); 1.021 (0.4); 0.984 (0.4); 0.940 (0.3); 0.935 (0.4); 0.789 (7.8); 0.774 (16.0); 0.759 (7.5); 0.432 (0.9); 0.424 (1.1); 0.420 (1.2); 0.412 (1.7); 0.404 (1.2); 0.400 (1.3); 0.391 (1.1); 0.240 (1.0); 0.231 (1.1); 0.228 (1.3); 0.220 (1.9); 0.212 (1.4); 0.209 (1.6); 0.200 (1.2); 0.069 (0.8); 0.012 (0.8); 0.006 (1.3); 0.000 (28.4); −0.007 (2.4); −0.010 (2.8); −0.017 (2.2); −0.024 (2.4); −0.030 (2.7); −0.040 (1.1); −0.043 (1.7); −0.052 (0.6) Example I-771: .sup.1H-NMR (300.2 MHz, d.sub.6-DMSO): δ = 9.009 (3.6); 8.993 (3.5); 8.436 (6.3); 7.783 (8.0); 5.414 (6.2); 4.429 (1.8); 4.379 (3.6); 4.300 (3.7); 4.250 (1.8); 3.778 (1.8); 3.742 (4.2); 3.706 (4.1); 3.671 (1.6); 3.345 (48.0); 3.268 (3.9); 3.182 (3.5); 3.134 (1.8); 2.525 (12.1); 2.407 (0.3); 1.062 (16.0); 0.988 (15.8); 0.024 (3.6) Example I-799: .sup.1H-NMR (300.2 MHz, CDCl.sub.3): δ = 9.064 (9.0); 9.047 (9.1); 8.241 (0.9); 8.203 (16.0); 8.037 (15.2); 8.026 (5.3); 7.659 (8.4); 7.643 (8.2); 7.300 (39.1); 5.337 (8.7); 5.224 (14.6); 4.427 (5.3); 4.380 (10.2); 4.286 (10.7); 4.240 (5.6); 3.826 (11.2); 3.211 (6.2); 3.166 (9.1); 2.975 (8.4); 2.930 (5.8); 2.253 (0.5); 2.180 (0.4); 2.045 (3.0); 1.989 (0.5); 1.974 (1.0); 1.963 (1.0); 1.948 (2.0); 1.933 (1.1); 1.922 (1.1); 1.907 (0.6); 1.792 (0.3); 1.749 (1.3); 1.650 (8.3); 1.612 (7.6); 1.352 (0.5); 1.291 (1.0); 1.261 (0.9); 1.246 (2.6); 1.235 (4.6); 1.221 (3.5); 1.210 (1.4); 1.181 (0.5); 1.166 (0.4); 1.132 (0.8); 1.117 (1.3); 1.105 (3.4); 1.094 (2.4); 1.090 (2.3); 1.079 (3.6); 1.069 (2.0); 1.054 (0.8); 0.908 (1.0); 0.890 (2.1); 0.880 (2.2); 0.873 (1.5); 0.863 (4.1); 0.854 (1.6); 0.845 (2.3); 0.835 (2.4); 0.818 (1.2); 0.273 (0.7); 0.261 (0.9); 0.254 (0.9); 0.243 (2.5); 0.231 (2.5); 0.225 (2.3); 0.214 (3.2); 0.203 (1.7); 0.196 (1.8); 0.186 (2.6); 0.170 (2.3); 0.156 (2.7); 0.143 (2.6); 0.129 (2.6); 0.105 (6.1); 0.084 (1.5); 0.072 (1.4); 0.066 (2.2); 0.053 (3.2); 0.046 (2.8); 0.036 (41.8); 0.023 (3.9); 0.005 (1.4); −0.054 (1.6); −0.072 (3.0); −0.084 (3.7); −0.102 (3.2); −0.116 (2.0); −0.134 (0.8)

Use Examples

Example A: In Vivo Preventive Test on Puccinia recondita (Brown Rust on Wheat)

[0260] Solvent: 5% by volume of Dimethyl sulfoxide [0261] 10% by volume of Acetone [0262] Emulsifier 1 μl of Tween® 80 per mg of active ingredient

[0263] The active ingredients are made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/Tween®80 and then diluted in water to the desired concentration.

[0264] The young plants of wheat are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/Tween® 80.

[0265] After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Puccinia recondita spores. The contaminated wheat plants are incubated for 24 hours at 20° C. and at 100% relative humidity and then for 10 days at 20° C. and at 70-80% relative humidity.

[0266] The test is evaluated 11 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease is observed.

[0267] In this test the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 500 ppm of active ingredient: I-592; I-745; I-799

[0268] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 500 ppm of active ingredient: I-368; I-530; I-593; I-713; I-771

Example B: In Vivo Preventive Test on Septoria tritici (Leaf Spot on Wheat)

[0269] Solvent: 5% by volume of Dimethyl sulfoxide [0270] 10% by volume of Acetone [0271] Emulsifier 1 μl of Tween® 80 per mg of active ingredient

[0272] The active ingredients are made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/Tween®80 and then diluted in water to the desired concentration.

[0273] The young plants of wheat are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/Tween® 80.

[0274] After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Septoria tritici spores. The contaminated wheat plants are incubated for 72 hours at 18° C. and at 100% relative humidity and then for 21 days at 20° C. and at 90% relative humidity.

[0275] The test is evaluated 24 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease is observed.

[0276] In this test the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 500 ppm of active ingredient: I-710

[0277] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 500 ppm of active ingredient: I-368; I-441; I-444; I-480; I-530; I-592; I-593; I-713; I-745; I-771

Example C: In Vivo Preventive Test on Sphaerotheca fuliginea (Powdery Mildew on Cucurbits)

[0278] Solvent: 5% by volume of Dimethyl sulfoxide [0279] 10% by volume of Acetone [0280] Emulsifier 1 μl of Tween® 80 per mg of active ingredient

[0281] The active ingredients are made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/Tween®80 and then diluted in water to the desired concentration.

[0282] The young plants of gherkin are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/Tween® 80.

[0283] After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Sphaerotheca fuliginea spores. The contaminated gherkin plants are incubated for 72 hours at 18° C. and at 100% relative humidity and then for 12 days at 20° C. and at 70-80% relative humidity.

[0284] The test is evaluated 15 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease is observed.

[0285] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 500 ppm of active ingredient: I-368; I-441; I-444; I-480; I-530; I-592; I-593; I-713; I-745; I-771; I-799

Example D: In Vivo Preventive Test on Uromyces appendiculatus (Bean Rust)

[0286] Solvent: 5% by volume of Dimethyl sulfoxide [0287] 10% by volume of Acetone [0288] Emulsifier of Tween® 80 per mg of active ingredient

[0289] The active ingredients are made soluble and homogenized in a mixture of Dimethyl sulfoxide/Acetone/Tween®80 and then diluted in water to the desired concentration.

[0290] The young plants of bean are treated by spraying the active ingredient prepared as described above. Control plants are treated only with an aqueous solution of Acetone/Dimethyl sulfoxide/Tween® 80.

[0291] After 24 hours, the plants are contaminated by spraying the leaves with an aqueous suspension of Uromyces appendiculatus spores. The contaminated bean plants are incubated for 24 hours at 20° C. and at 100% relative humidity and then for 10 days at 20° C. and at 70-80% relative humidity.

[0292] The test is evaluated 11 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease is observed.

[0293] In this test the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 500 ppm of active ingredient: I-441

[0294] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 500 ppm of active ingredient: I-368; I-530; I-592; I-593; I-713; I-745; I-771; I-799

Example E: In Vivo Preventive Test on Phakopsora Test (Soybeans)

[0295] Solvent: 24.5 parts by weight of acetone [0296] 24.5 parts by weight of dimethylacetamide [0297] Emulsifier 1 part by weight of alkylaryl polyglycol ether

[0298] To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

[0299] To test for preventive activity, young plants are sprayed with the preparation of active compound at the stated rate of application. After the spray coating has dried on, the plants are inoculated with an aqueous spore suspension of the causal agent of soybean rust (Phakopsora pachyrhizi) and stay for 24 h without light in an incubation cabinet at approximately 24° C. and a relative atmospheric humidity of 95%.

[0300] The plants remain in the incubation cabinet at approximately 24° C. and a relative atmospheric humidity of approximately 80% and a day/night interval of 12 h.

[0301] The test is evaluated 7 days after the inoculation. 0% means an efficacy which corresponds to that of the untreated control, while an efficacy of 100% means that no disease is observed.

[0302] In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 10 ppm of active ingredient: I-530; I-713; I-771