SUBSTITUTED SULFONYL AMIDES FOR CONTROLLING ANIMAL PESTS

Abstract

The invention relates to the compound of the formula (I) in which R.sup.1, R.sup.2 and D have the meanings given in the description, and to the use thereof for controlling animal pests and particularly nematodes.

##STR00001##

Claims

1. A compound of formula (I) ##STR00051## where R.sup.1 and R.sup.2 are each independently selected from chlorine and bromine, where R.sup.1 and R.sup.2 are not both chlorine, where D is a phenyl radical which is unsubstituted or substituted by one or more R.sup.3 radicals, where the substituent(s) R.sup.3 is/are each independently selected from: cyano, halogen, acetyl, (C.sub.3-C.sub.6)cycloalkyl, (C.sub.3-C.sub.6)cycloalkyloxy, (C.sub.3-C.sub.6)cycloalkyl(C.sub.3-C.sub.8)cycloalkyl, (C.sub.1-C.sub.6)alkyl-(C.sub.3-C.sub.6)cycloalkyl, halo(C.sub.3-C.sub.6)cycloalkyl, (C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)haloalkyl, (C.sub.1-C.sub.6)cyanoalkyl, (C.sub.1-C.sub.6)hydroxyalkyl, hydroxycarbonyl(C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)alkoxycarbonyl-(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkyl, (C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)haloalkenyl, (C.sub.2-C.sub.6)cyanoalkenyl, (C.sub.2-C.sub.6)alkynyl, (C.sub.2-C.sub.6)haloalkynyl, (C.sub.2-C.sub.6)cyanoalkynyl, (C.sub.1-C.sub.6)alkoxy, (C.sub.1-C.sub.6)haloalkoxy, (C.sub.1-C.sub.6)cyanoalkoxy, (C.sub.1-C.sub.6)alkoxycarbonyl-(C.sub.1-C.sub.6)alkoxy, (C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkoxy, (C.sub.1-C.sub.6)alkoxyimino, (C.sub.1-C.sub.6)alkyl-(C.sub.1-C.sub.6)alkoxyimino, (C.sub.1-C.sub.6)haloalkyl(C.sub.1-C.sub.6)alkoxyimino, (C.sub.1-C.sub.6)alkylthio, (C.sub.1-C.sub.6)haloalkylthio, (C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylthio, (C.sub.1-C.sub.6)alkylthio-(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkylsulfinyl, (C.sub.1-C.sub.6)haloalkylsulfinyl, (C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulfinyl, (C.sub.1-C.sub.6)alkylsulfinyl-(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkylsulfonyl, (C.sub.1-C.sub.6)haloalkylsulfonyl, (C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulfonyl, (C.sub.1-C.sub.6)alkylsulfonyl-(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkylsulfonyloxy, (C.sub.1-C.sub.6)alkylcarbonyl, (C.sub.1-C.sub.6)haloalkylcarbonyl, (C.sub.1-C.sub.6)alkylcarbonyloxy, (C.sub.1-C.sub.6)alkoxycarbonyl, (C.sub.1-C.sub.6)haloalkoxycarbonyl, aminocarbonyl, (C.sub.1-C.sub.6)alkylaminocarbonyl, di(C.sub.1-C.sub.6)alkylaminocarbonyl, (C.sub.2-C.sub.6)alkenylaminocarbonyl, di(C.sub.2-C.sub.6)alkenylaminocarbonyl, (C.sub.3-C.sub.8)cycloalkylaminocarbonyl, (C.sub.1-C.sub.6)alkylsulfonylamino, (C.sub.1-C.sub.6)alkylamino, di(C.sub.1-C.sub.6)alkylamino, (C.sub.3-C.sub.8)cycloalkylamino, (C.sub.1-C.sub.6)alkylcarbonylamino, (1-pyrazolyl)(C.sub.1-C.sub.3)alkyl and/or (C.sub.1-C.sub.3)alkoxypyrimidinyloxy.

2. The compound of formula (I) as claimed in claim 1, wherein D is a phenyl radical which is unsubstituted or substituted by one or more R.sup.3 radicals, where the substituent(s) R.sup.3 is/are each independently selected from: cyano, halogen, acetyl, (C.sub.3-C.sub.6)cycloalkyl, (C.sub.3-C.sub.6)cycloalkyloxy, (C.sub.3-C.sub.6)cycloalkyl(C.sub.3-C.sub.8)cycloalkyl, (C.sub.1-C.sub.6)alkyl-(C.sub.3-C.sub.6)cycloalkyl, halo(C.sub.3-C.sub.6)cycloalkyl, (C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)haloalkyl, (C.sub.1-C.sub.6)cyanoalkyl, (C.sub.1-C.sub.6)hydroxyalkyl, hydroxycarbonyl(C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)alkoxycarbonyl-(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkoxy, (C.sub.1-C.sub.6)haloalkoxy, (C.sub.1-C.sub.6)cyanoalkoxy, (C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkoxy, (C.sub.1-C.sub.6)alkoxyimino, (C.sub.1-C.sub.6)alkyl-(C.sub.1-C.sub.6)alkoxyimino, (C.sub.1-C.sub.6)haloalkyl-(C.sub.1-C.sub.6)alkoxyimino, (C.sub.1-C.sub.6)alkylthio, (C.sub.1-C.sub.6)haloalkylthio, (C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylthio, (C.sub.1-C.sub.6)alkylthio-(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkylsulfinyl, (C.sub.1-C.sub.6)haloalkylsulfinyl, (C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulfinyl, (C.sub.1-C.sub.6)alkylsulfinyl-(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkylsulfonyl, (C.sub.1-C.sub.6)haloalkylsulfonyl, (C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulfonyl, (C.sub.1-C.sub.6)alkylsulfonyl-(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkylsulfonyloxy, (C.sub.1-C.sub.6)alkylcarbonyl, (C.sub.1-C.sub.6)haloalkylcarbonyl, (C.sub.1-C.sub.6)alkylcarbonyloxy, (C.sub.1-C.sub.6)alkoxycarbonyl, (C.sub.1-C.sub.6)haloalkoxycarbonyl, aminocarbonyl, (C.sub.1-C.sub.6)alkylaminocarbonyl, di(C.sub.1-C.sub.6)alkylaminocarbonyl, (C.sub.2-C.sub.6)alkenylaminocarbonyl, (C.sub.3-C.sub.8)cycloalkylaminocarbonyl, (C.sub.1-C.sub.6)alkylsulfonylamino, (C.sub.1-C.sub.6)alkylamino, di(C.sub.1-C.sub.6)alkylamino, (C.sub.3-C.sub.6)cycloalkylamino, (C.sub.1-C.sub.6)alkylcarbonylamino, and/or (C.sub.1-C.sub.3)alkoxypyrimidinyloxy.

3. The compound of formula (I) as claimed in claim 1, wherein D is a phenyl radical which is unsubstituted or substituted by one or more R.sup.3 radicals, where the substituent(s) R.sup.3 is/are each independently selected from: where the substituent(s) R.sup.3 is/are each independently selected from: halogen, (C.sub.3-C.sub.6)cycloalkyloxy, (C.sub.3-C.sub.6)cycloalkyl-(C.sub.3-C.sub.8)cycloalkyl, (C.sub.1-C.sub.6)alkyl-(C.sub.3-C.sub.6)cycloalkyl, halo(C.sub.3-C.sub.6)cycloalkyl, (C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)haloalkyl, (C.sub.1-C.sub.6)alkoxy(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkoxy, (C.sub.1-C.sub.6)haloalkoxy and (C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkoxy.

4. The compound of formula (I) as claimed in claim 1, wherein D is a phenyl radical which is unsubstituted or substituted by one or more R.sup.3 radicals, where the substituent(s) R.sup.3 is/are each independently selected from: halogen, (C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkoxy and (C.sub.1-C.sub.6)haloalkoxy.

5. The compound of formula (I) as claimed in claim 1, wherein D is a radical of formula (V1) to (V7) ##STR00052##

6. The compound of formula (I′) ##STR00053## Where R.sup.1 and R.sup.2 are each independently selected from chlorine and bromine, where R.sup.1 and R.sup.2 are not both chlorine, where D is a phenyl radical which is unsubstituted or substituted by one or more R.sup.3 radicals, where the substituent(s) R.sup.3 is/are each independently selected from: cyano, halogen, acetyl, (C.sub.3-C.sub.6)cycloalkyl, (C.sub.3-C.sub.6)cycloalkyloxy, (C.sub.3-C.sub.6)cycloalkyl(C.sub.3-C.sub.8)cycloalkyl, (C.sub.1-C.sub.6)alkyl-(C.sub.3-C.sub.6)cycloalkyl, halo(C.sub.3-C.sub.6)cycloalkyl, (C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)haloalkyl, (C.sub.1-C.sub.6)cyanoalkyl, (C.sub.1-C.sub.6)hydroxyalkyl, hydroxycarbonyl(C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)alkoxycarbonyl-(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkyl, (C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)haloalkenyl, (C.sub.2-C.sub.6)cyanoalkenyl, (C.sub.2-C.sub.6)alkynyl, (C.sub.2-C.sub.6)haloalkynyl, (C.sub.2-C.sub.6)cyanoalkynyl, (C.sub.1-C.sub.6)alkoxy, (C.sub.1-C.sub.6)haloalkoxy, (C.sub.1-C.sub.6)cyanoalkoxy, (C.sub.1-C.sub.6)alkoxycarbonyl-(C.sub.1-C.sub.6)alkoxy, (C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkoxy, (C.sub.1-C.sub.6)alkoxyimino, (C.sub.1-C.sub.6)alkyl-(C.sub.1-C.sub.6)alkoxyimino, (C.sub.1-C.sub.6)haloalkyl(C.sub.1-C.sub.6)alkoxyimino, (C.sub.1-C.sub.6)alkylthio, (C.sub.1-C.sub.6)haloalkylthio, (C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylthio, (C.sub.1-C.sub.6)alkylthio-(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkylsulfinyl, (C.sub.1-C.sub.6)haloalkylsulfinyl, (C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulfinyl, (C.sub.1-C.sub.6)alkylsulfinyl-(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkylsulfonyl, (C.sub.1-C.sub.6)haloalkylsulfonyl, (C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulfonyl, (C.sub.1-C.sub.6)alkylsulfonyl-(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkylsulfonyloxy, (C.sub.1-C.sub.6)alkylcarbonyl, (C.sub.1-C.sub.6)haloalkylcarbonyl, (C.sub.1-C.sub.6)alkylcarbonyloxy, (C.sub.1-C.sub.6)alkoxycarbonyl, (C.sub.1-C.sub.6)haloalkoxycarbonyl, aminocarbonyl, (C.sub.1-C.sub.6)alkylaminocarbonyl, di(C.sub.1-C.sub.6)alkylaminocarbonyl, (C.sub.2-C.sub.6)alkenylaminocarbonyl, di(C.sub.2-C.sub.6)alkenylaminocarbonyl, (C.sub.3-C.sub.8)cycloalkylaminocarbonyl, (C.sub.1-C.sub.6)alkylsulfonylamino, (C.sub.1-C.sub.6)alkylamino, di(C.sub.1-C.sub.6)alkylamino, (C.sub.3-C.sub.8)cycloalkylamino, (C.sub.1-C.sub.6)alkylcarbonylamino, (1-pyrazolyl)(C.sub.1-C.sub.3)alkyl and/or (C.sub.1-C.sub.3)alkoxypyrimidinyloxy. and x is 0, 1 or 2.

7. The compound of formula (I-1″) or (I-2″) ##STR00054## Where R.sup.1 and R.sup.2 are each independently selected from chlorine and bromine, where R.sup.1 and R.sup.2 are not both chlorine, where D is a phenyl radical which is unsubstituted or substituted by one or more R.sup.3 radicals, where the substituent(s) R.sup.3 is/are each independently selected from: cyano, halogen, acetyl, (C.sub.3-C.sub.6)cycloalkyl, (C.sub.3-C.sub.6)cycloalkyloxy, (C.sub.3-C.sub.6)cycloalkyl(C.sub.3-C.sub.8)cycloalkyl, (C.sub.1-C.sub.6)alkyl-(C.sub.3-C.sub.6)cycloalkyl, halo(C.sub.3-C.sub.6)cycloalkyl, (C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)haloalkyl, (C.sub.1-C.sub.6)cyanoalkyl, (C.sub.1-C.sub.6)hydroxyalkyl, hydroxycarbonyl(C.sub.1-C.sub.6)-alkoxy, (C.sub.1-C.sub.6)alkoxycarbonyl-(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkyl, (C.sub.2-C.sub.6)alkenyl, (C.sub.2-C.sub.6)haloalkenyl, (C.sub.2-C.sub.6)cyanoalkenyl, (C.sub.2-C.sub.6)alkynyl, (C.sub.2-C.sub.6)haloalkynyl, (C.sub.2-C.sub.6)cyanoalkynyl, (C.sub.1-C.sub.6)alkoxy, (C.sub.1-C.sub.6)haloalkoxy, (C.sub.1-C.sub.6)cyanoalkoxy, (C.sub.1-C.sub.6)alkoxycarbonyl-(C.sub.1-C.sub.6)alkoxy, (C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkoxy, (C.sub.1-C.sub.6)alkoxyimino, (C.sub.1-C.sub.6)alkyl-(C.sub.1-C.sub.6)alkoxyimino, (C.sub.1-C.sub.6)haloalkyl(C.sub.1-C.sub.6)alkoxyimino, (C.sub.1-C.sub.6)alkylthio, (C.sub.1-C.sub.6)haloalkylthio, (C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylthio, (C.sub.1-C.sub.6)alkylthio-(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkylsulfinyl, (C.sub.1-C.sub.6)haloalkylsulfinyl, (C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulfinyl, (C.sub.1-C.sub.6)alkylsulfinyl-(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkylsulfonyl, (C.sub.1-C.sub.6)haloalkylsulfonyl, (C.sub.1-C.sub.6)alkoxy-(C.sub.1-C.sub.6)alkylsulfonyl, (C.sub.1-C.sub.6)alkylsulfonyl-(C.sub.1-C.sub.6)alkyl, (C.sub.1-C.sub.6)alkylsulfonyloxy, (C.sub.1-C.sub.6)alkylcarbonyl, (C.sub.1-C.sub.6)haloalkylcarbonyl, (C.sub.1-C.sub.6)alkylcarbonyloxy, (C.sub.1-C.sub.6)alkoxycarbonyl, (C.sub.1-C.sub.6)haloalkoxycarbonyl, aminocarbonyl, (C.sub.1-C.sub.6)alkylaminocarbonyl, di(C.sub.1-C.sub.6)alkylaminocarbonyl, (C.sub.2-C.sub.6)alkenylaminocarbonyl, di(C.sub.2-C.sub.6)alkenylaminocarbonyl, (C.sub.3-C.sub.8)cycloalkylaminocarbonyl, (C.sub.1-C.sub.6)alkylsulfonylamino, (C.sub.1-C.sub.6)alkylamino, di(C.sub.1-C.sub.6)alkylamino, (C.sub.3-C.sub.8)cycloalkylamino, (C.sub.1-C.sub.6)alkylcarbonylamino, (1-pyrazolyl)(C.sub.1-C.sub.3)alkyl and/or (C.sub.1-C.sub.3)alkoxypyrimidinyloxy.

8. The compound of formula (I), as claimed in claim 1, wherein R.sup.3 is in each case independently selected from halogen, (C.sub.1-C.sub.3)alkyl, (C.sub.1-C.sub.3)alkoxy and (C.sub.1-C.sub.3)haloalkoxy.

9. The product comprising one or more compounds of formula (I), as claimed in claim 1 for control of animal pests, optionally nematodes.

10. The product comprising one or more compounds of the formula (I), as claimed in claim 1 for protection of propagation material of one or more plants.

11. A method of controlling one or more animal pests, optionally nematodes, comprising allowing at least one compound of the formula (I), as claimed in claim 1 to act on the animal pests, optionally nematodes, and/or a habitat thereof.

12. An agrochemical formulation comprising at least one compound of formula (I), as claimed in claim 1 in a biologically effective amount of between 0.00000001% and 98% by weight based on the weight of the agrochemical formulation, and one or more extenders and/or surfactants.

13. The agrochemical formulation as claimed in claim 12, additionally comprising a further agrochemically active ingredient.

Description

PREPARATION EXAMPLES

[0433] The preparation and use examples which follow illustrate the invention without limiting it.

[0434] Analytical Determinations

[0435] The analytical determination methods described below apply to all statements in the entire document unless the respective analytical determination method is specially described in the relevant text passage.

[0436] Mass Spectrometry

[0437] The determination of [M+H].sup.+ or M- by LC-MS under acidic chromatographic conditions was carried out using 1 ml of formic acid per liter of acetonitrile and 0.9 ml of formic acid per liter of Millipore water as eluents. The Zorbax Eclipse Plus C18 column, 50 mm*2.1 mm, was used, at a column oven temperature of 55° C.

[0438] Instruments:

[0439] LC-MS3: Waters UPLC with SQD2 mass spectrometer and SampleManager sample changer. Linear gradient from 0.0 to 1.70 minutes from 10% acetonitrile to 95% acetonitrile, from 1.70 to 2.40 minutes constant 95% acetonitrile, flow rate 0.85 ml/min.

[0440] LC-MS6 and LC-MS7: Agilent 1290 LC, Agilent MSD, HTS PAL sample changer. Linear gradient from 0.0 to 1.80 minutes from 10% acetonitrile to 95% acetonitrile, from 1.80 to 2.50 minutes constant 95% acetonitrile, flow rate 1.0 ml/min.

[0441] The determination of [M+H].sup.+ by LC-MS under neutral chromatographic conditions was carried out using acetonitrile and Millipore water with 79 mg/l ammonium carbonate as eluents.

[0442] Instruments:

[0443] LC-MS4: Waters IClass Acquity with QDA mass spectrometer and FTN sample changer (column Waters Acquity 1.7 μm 50 mm*2.1 mm, oven temperature 45° C.). Linear gradient from 0.0 to 2.10 minutes from 10% acetonitrile to 95% acetonitrile, from 2.10 to 3.00 minutes constant 95% acetonitrile, flow rate 0.7 ml/min.

[0444] LC-MSS: Agilent 1100 LC system with MSD mass spectrometer and HTS PAL sample changer (column: Zorbax XDB C18 1.8 μm 50 mm*4.6 mm, oven temperature 55° C.). Linear gradient from 0.0 to 4.25 minutes from 10% acetonitrile to 95% acetonitrile, from 4.25 to 5.80 minutes constant 95% acetonitrile, flow rate 2.0 ml/min.

[0445] In all cases, the retention time indices were determined according to a homologous series of straight-chain alkan-2-ones having 3 to 16 carbons, where the index of the first alkanone was set to 300, the index of the last alkanone was set to 1600 and linear interpolation was carried out between the values of successive alkanones.

[0446] The .sup.1H NMR spectra were measured with a Bruker Avance III 400 MHz spectrometer fitted with a 1.7 mm TCI sample head using tetramethylsilane as standard (0.00 ppm), and the measurements recorded were generally of solutions in the solvents CD.sub.3CN, CDCl.sub.3 or d.sub.6-DMSO. Alternatively, a Bruker Avance III 600 MHz spectrometer fitted with a 5 mm CPNMP sample head or a Bruker Avance NEO 600 MHz spectrometer fitted with a 5 mm TCI sample head was employed for the measurements. In general, the measurements were carried out at a sample head temperature of 298 K. If other measurement temperatures were used, this is specifically mentioned.

[0447] NMR Peak List Method

[0448] The .sup.1H NMR data of selected examples are represented in the form of .sup.1H NMR peak lists. For each signal peak, first the a value in ppm and then the signal intensity in round brackets are listed. The 6 value/signal intensity number pairs are listed with separation from one another by semicolons.

[0449] The peak list for one example therefore has the form:

[0450] δ.sub.1 (intensity.sub.1); δ.sub.2 (intensity.sub.2); . . . ; δ.sub.i (intensity.sub.i); . . . ; δ.sub.n (intensity.sub.n)

[0451] The intensity of sharp signals correlates with the height of the signals in a printed representation of a .sup.1H NMR spectrum in cm and shows the true ratios of the signal intensities. In the case of broad signals, several peaks or the middle of the signal and the relative intensity thereof may be shown in comparison to the most intense signal in the spectrum.

[0452] Calibration of the chemical shift of .sup.1H NMR spectra is accomplished using tetramethylsilane or the chemical shift of the solvent if the sample does not contain any tetramethylsilane. Accordingly, in certain cases the .sup.1H NMR peak lists may comprise the tetramethylsilane peak.

[0453] The .sup.1H NMR peak lists are equivalent to conventional .sup.1H NMR representations and thus usually contain all peaks also listed in conventional .sup.1H NMR interpretations.

[0454] In addition, like conventional .sup.1H NMR representations, they may show solvent signals, signals of stereoisomers of the compounds which may be part of the subject matter of the invention, and/or peaks of impurities.

[0455] .sup.1H NMR solvent signals, the tetramethylsilane signal and the water signal in the solvent in question are excluded from the calibration of the relative intensity since their stated intensity values can be very high.

[0456] The peaks of stereoisomers of the compounds of the invention and/or peaks of impurities usually have a lower intensity than the peaks of the compounds of the invention (for example at a purity of >90%).

[0457] Such stereoisomers and/or impurities may be typical of the particular preparation process. Their peaks can thus help in this case to identify reproduction of a preparation process with reference to “by-product fingerprints”.

[0458] An expert calculating the peaks of the target compounds by known methods (MestreC, ACD simulation, but also with empirically evaluated expected values) can, if required, identify the peaks of the target compounds, optionally using additional intensity filters. This identification is equivalent to the relevant peak listing in conventional .sup.1H NMR interpretation.

[0459] The solvent utilized can be read off from the JCAMP file from the parameter “solvent”, the measurement frequency of the spectrometer from “observe frequency”, and the spectrometer model from “spectrometer/data system”.

[0460] .sup.13C NMR data are reported analogously to the .sup.1H NMR data as peak lists using broadband-decoupled .sup.13C NMR spectra. .sup.13C NMR solvent signals and tetramethylsilane are excluded from the calibration of the relative intensity since these signals may have very high intensity values.

[0461] Further details of NMR data description using peak lists can be found in: “Citation of NMR Peaklist Data within Patent Applications” in Research Disclosure Database Number 564025.

[0462] log P Values

[0463] The log P values were determined according to EEC Directive 79/831 Annex V.A8 by HPLC (high-performance liquid chromatography) on a reversed-phase column (C.sub.18) using the following methods:

[0464] .sup.[a] The log P value is determined by LC-UV measurement in the acidic range using 0.9 ml/1 formic acid in water and 1.0 ml/l formic acid in acetonitrile as eluents (linear gradient from 10% acetonitrile to 95% acetonitrile).

[0465] .sup.[b] The log P value is determined by LC-UV measurement in the neutral range using 0.001 molar ammonium acetate solution in water and acetonitrile as eluents (linear gradient from 10% acetonitrile to 95% acetonitrile).

[0466] Calibration was carried out using straight-chain alkan-2-ones (having 3 to 16 carbon atoms) with known log P values. The values between successive alkanones are determined by linear regression.

Preparation of ethyl 5-amino-1-[2-(trifluoromethyl)cyclopropyl]-1H-imidazole-4-carboxylate

[0467] ##STR00013##

[0468] 11 g (109 mmol) of triethylamine was added to a mixture of 30 g (97.7 mmol) of ethyl aminocyanoacetate tosylate and 15 g (101 nmol) of triethyl orthoformate in 500 ml of acetonitrile, and the mixture was heated under reflux for 1 h. After addition of 16.2 g (100 mmol) of 2-trifluoromethylcyclopropanamine hydrochloride and a further 11 g (109 mmol) of triethylamine, the mixture was heated at reflux for 1 h, then concentrated under reduced pressure, and water (200 ml) was added to the residue. The undissolved constituents were filtered off and recrystallized from hexane-MTBE (7:3). Yield 12 g (45.6 mmol, 45%).

Preparation of ethyl 5-amino-2-chloro-1-[2-(trifluoromethyl)cyclopropyl]-1H-imidazole-4-carboxylate

[0469] ##STR00014##

[0470] 12 g (45.6 mmol) of ethyl 5-amino-1-[2-(trifluoromethyl)cyclopropyl]-1H-imidazole-4-carboxylate from the preceding stage was dissolved in 200 ml of acetonitrile, 9.3 g (54.6 mmol) of copper(II) chloride dihydrate was added and the mixture was heated at reflux for 72 h, then concentrated under reduced pressure, and aqueous potassium carbonate was added to the residue. The mixture was extracted three times with 300 ml each time of dichloromethane, and the combined organic phases were dried with sodium sulfate and concentrated under reduced pressure. The residue was recrystallized from hexane/ethyl acetate (9:1). Yield 7.5 g (25.2 mmol, 55%).

Preparation of ethyl 5-bromo-2-chloro-1-[2-(trifluoromethyl)cyclopropyl]-1H-imidazole-4-carboxylate

[0471] ##STR00015##

[0472] 2.08 g (20 mmol) of tert-butyl nitrite was added dropwise to a stirred mixture of 5 g (17 mmol) of ethyl 5-amino-2-chloro-1-[2-(trifluoromethyl)cyclopropyl]-1H-imidazole-4-carboxylate from the preceding stage and 2.89 g (20 mmol) of copper(I) bromide in 100 ml of acetonitrile. After 3 h, the mixture was concentrated under reduced pressure, and aqueous potassium carbonate was added to the residue. The mixture was extracted three times with 300 ml each time of dichloromethane, and the combined organic phases were dried with sodium sulfate and concentrated under reduced pressure, giving 4.25 g (11.8 mmol, 70%).

Preparation of 5-bromo-2-chloro-1-[2-(trifluoromethyl)cyclopropyl]-1H-imidazole-4-carboxylic acid

[0473] ##STR00016##

[0474] 2.0 g (5.5 mmol) of ethyl 5-bromo-2-chloro-1-[2-(trifluoromethyl)cyclopropyl]-1H-imidazole-4-carboxylate from the preceding stage and 0.46 g (11 mmol) of lithium hydroxide were stirred in a mixture of 50 ml of THF and 20 ml of water. After 1 d, the mixture was concentrated under reduced pressure, stirred with 50 ml of water and filtered. The filtrate was acidified with conc. HCl to pH=3-4, and the precipitate formed was filtered off and dried. This gave 1.58 g of 5-bromo-2-chloro-1-[2-(trifluoromethyl)cyclopropyl]-1H-imidazole-4-carboxylic acid (86%).

[0475] .sup.1H NMR (400 MHz, DMSO-d.sub.6) δ 12.83 (s, 1H), 3.78 (dt, J=8.3, 4.4 Hz, 1H), 2.79 (dtd, J=10.4, 6.9, 3.6 Hz, 1H), 1.73 (m, 2H).

[0476] LCMS (API-ES Pos, M+H) 332.9

[0477] LCMS (API-ES Neg, M−H) 330.7

Preparation of 5-bromo-2-chloro-N-[(2-methylphenyl)sulfonyl]-1-[2-(trifluoromethyl)cyclopropyl]-1H-imidazole-4-carboxamide

[0478] ##STR00017##

[0479] To 100 mg (0.3 mmol) of 5-bromo-2-chloro-1-[2-(trifluoromethyl)cyclopropyl]-1H-imidazole-4-carboxylic acid from the preceding stage in 5 ml of dichloromethane were added 110 mg (0.9 mmol) of 4-dimethylaminopyridine and 51 mg (0.3 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, and after stirring for 20 min, 88 mg (0.39 mmol) of 2-chloro-5-methoxybenzenesulfonamide was added. Stirring of the mixture was continued. The next day, 1M HCl was added, the mixture was extracted three times with dichloromethane, and the combined organic phases were dried with Na.sub.2SO.sub.4 and concentrated under reduced pressure. The residue was purified by RP chromatography (RP-18, acetonitrile/water, 0.1% HCOOH). Yield 67.2 mg (46%).

[0480] LC-MS (API, ESI-Pos, M+1): 487.8

Preparation of ethyl 5-amino-2-bromo-1-[2-(trifluoromethyl)cyclopropyl]-1H-imidazole-4-carboxylate

[0481] ##STR00018##

[0482] To a solution of 5.1 g (19 mmol) of ethyl 5-amino-1-[2-(trifluoromethyl)cyclopropyl]-1H-imidazole-4-carboxylate (see above) in 100 ml of acetonitrile was added 5.2 g (23 mmol) of copper(II) bromide. The mixture was heated under reflux for 72 h, then concentrated under reduced pressure, and aqueous potassium carbonate was added to the residue. The mixture was extracted three times with 100 ml each time of dichloromethane, and the combined organic phases were dried with sodium sulfate and concentrated under reduced pressure. The residue was recrystallized from hexane/ethyl acetate (4:1). Yield 4.3 g (65%).

Preparation of ethyl 2,5-dibromo-1-[2-(trifluoromethyl)cyclopropyl]-1H-imidazole-4-carboxylate

[0483] ##STR00019##

[0484] 1.36 g (13.2 mmol) of tert-butyl nitrite was added dropwise to a stirred mixture of 4.3 g (11.4 mmol) of ethyl 5-amino-2-bromo-1-[2-(trifluoromethyl)cyclopropyl]-1H-imidazole-4-carboxylate from the preceding stage and 1.9 g (13.2 mmol) of copper(I) bromide in 100 ml of acetonitrile. After 3 h, the mixture was concentrated under reduced pressure, and aqueous potassium carbonate was added to the residue. The mixture was extracted three times with 150 ml each time of dichloromethane, and the combined organic phases were dried with sodium sulfate and concentrated under reduced pressure, giving 3.1 g (67%).

Preparation of 2,5-dibromo-1-[(1S,2S)-2-(trifluoromethyl)cyclopropyl]-1H-imidazole-4-carboxylic acid

[0485] ##STR00020##

[0486] 3.1 g (7.3 mmol) of ethyl 2,5-dibromo-1-[2-(trifluoromethyl)cyclopropyl]-1H-imidazole-4-carboxylate from the preceding stage and 0.6 g (14.2 mmol) of lithium hydroxide were stirred in a mixture of 50 ml of THF and 20 ml of water. After 1 d, the mixture was concentrated under reduced pressure, stirred with 50 ml of water and filtered. The filtrate was acidified with conc. HCl to pH=3-4, and the precipitate formed was filtered off and dried. This gave 2.25 g (84%).

[0487] .sup.1H NMR (400 MHz, DMSO-d.sub.6) δ 12.82 (s, 1H), 3.79 (dt, J=8.3, 4.4 Hz, 1H), 2.80 (dtd, J=10.4, 6.9, 3.5 Hz, 1H), 1.73 (m, 2H).

[0488] LCMS (API-ES Pos, M+H) 378.8

[0489] LCMS (API-ES Neg, M−H) 376.8

Preparation of 2,5-dibromo-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-1-[2-(trifluoromethyl)cyclopropyl]-1H-imidazole-4-carboxamide

[0490] ##STR00021##

[0491] To 150 mg (0.39 mmol) of 2,5-dibromo-1-[(1S,2S)-2-(trifluoromethyl)cyclopropyl]-1H-imidazole-4-carboxylic acid from the preceding stage in 5 ml of dichloromethane were added 145 mg (1.19 mmol) of 4-dimethylaminopyridine and 228 mg (1.19 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, and after stirring for 20 min, 88 mg (0.39 mmol) of 2-chloro-5-methoxybenzenesulfonamide was added. Stirring of the mixture was continued. The next day, 1M HCl was added, the mixture was extracted three times with dichloromethane, and the combined organic phases were dried with Na.sub.2SO.sub.4 and concentrated under reduced pressure. The residue was purified by RP chromatography (RP-18, acetonitrile/water, 0.1% HCOOH). Yield 86.5 mg (37%).

[0492] LC-MS (API, ESI-Pos, M+1): 581.7

Preparation of ethyl 5-chloro-1-[2-(trifluoromethyl)cyclopropyl]-1H-imidazole-4-carboxylate

[0493] ##STR00022##

[0494] 5.64 g (55 mmol) of tert-butyl nitrite was added dropwise to a stirred mixture of 12 g (45.6 mmol) of ethyl 5-amino-1-[2-(trifluoromethyl)cyclopropyl]-1H-imidazole-4-carboxylate (see above) and 5.42 g (55 mmol) of copper(I) chloride in 50 ml of acetonitrile. After 3 h, the mixture was concentrated under reduced pressure, and aqueous potassium carbonate was added to the residue. The mixture was extracted three times with 100 ml each time of dichloromethane, and the combined organic phases were dried with sodium sulfate and concentrated under reduced pressure; purification by chromatography gave 3.2 g (25%).

Preparation of ethyl 5-chloro-1-[2-(trifluoromethyl)cyclopropyl]-1H-imidazole-4-carboxylate

[0495] ##STR00023##

[0496] Added dropwise to a solution of lithium diisopropylamide in THF (prepared from 0.81 g (8 mmol) of diisopropylamine and 3.2 ml (8 mmol) of n-butyllithium 2.5M) was 2 g (7.08 mmol) of ethyl 5-chloro-1-[2-(trifluoromethyl)cyclopropyl]-1H-imidazole-4-carboxylate from the preceding stage as a solution in THF while cooling in a CO2 bath. After 1 h, 2.58 g (10 mmol) of 1,2-dibromo-1,1,2,2-tetrafluoroethane was added dropwise and the mixture was allowed to thaw to room temperature. The mixture was diluted with MTBE and admixed with aq. NH4Cl. The organic phase was washed with aq. NaCl, dried with Na.sub.2SO.sub.4 and concentrated under reduced pressure; purification by chromatography gave 0.21 g (8%).

Preparation of 2-bromo-5-chloro-1-[2-(trifluoromethyl)cyclopropyl]-1H-imidazole-4-carboxylic acid

[0497] ##STR00024##

[0498] 0.3 g (0.83 mmol) of ethyl 5-chloro-1-[2-(trifluoromethyl)cyclopropyl]-1H-imidazole-4-carboxylate from the preceding stage and 0.07 g (1.67 mmol) of lithium hydroxide were stirred in a mixture of 20 ml of THF and 10 ml of water. The mixture was concentrated under reduced pressure, stirred with 40 ml of water and filtered. The filtrate was acidified with conc. HCl to pH=3-4, and the precipitate formed was filtered off and dried. This gave 0.19 g (68%).

[0499] 1H-NMR (400 MHz, DMSO-D.sub.6, ppm): δ 12.82 (br.s, 1H), 3.76 (s, 1H), 2.79 (s, 1H), 1.71 (t, 2H)

[0500] LC-MS (API, ESI-Pos, M+1): 335.0

Preparation of 2-bromo-5-chloro-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-1-[2-(trifluoromethyl)cyclopropyl]-1H-imidazole-4-carboxamide

[0501] ##STR00025##

[0502] To 180 mg (0.54 mmol) of 2-bromo-5-chloro-1-[(1S,2S)-2-(trifluoromethyl)cyclopropyl]-1H-imidazole-4-carboxylic acid from the preceding stage in 50 ml of dichloromethane were added 198 mg (1.62 mmol) of 4-dimethylaminopyridine and 310 mg (1.62 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride 221 mg (0.54 mmol) of 2-chloro-5-methoxybenzenesulfonamide. Stirring of the mixture was continued. After three days, aq. NaCl and aq. citric acid were added, the mixture was extracted twice with dichloromethane, and the combined organic phases were dried with Na2SO4 and concentrated under reduced pressure. The residue was purified by RP chromatography (RP-18, acetonitrile/water, 0.1% HCOOH). Yield 188 mg (63%).

[0503] LC-MS (HCOOH, ESI-Pos, M+1): 537.9

[0504] Table 1 below lists further compounds of the formula (I) which were prepared analogously to the examples given above. The acid precursors were either synthesized as described above.

##STR00026##

TABLE-US-00001 Fraction No. Structure I-01 [00027] .sup.1H NMR(400.2 MHz, d.sub.6-DMSO): δ = 7.5765 (3.0); 7.5681 (4.4); 7.5453 (3.2); 7.2887 (1.6); 7.2810 (1.5); 7.2666 (1.3); 7.2589 (1.3); 3.8523 (16.0); 3.8040 (0.5); 3.7920 (0.8); 3.7833 (1.0); 3.7748 (0.7); 3.7720 (0.6); 3.7626 (0.5); 3.3384 (1.5); 2.8053 (0.4); 2.7966 (0.5); 2.7880 (0.5); 2.7794 (0.5); 2.7705 (0.4); 2.5241 (0.7); 12.5193 (1.0); 2.5105 (15.7); 2.5061 (32.4); 2.5015 (42.6); 2.4969 (30.3); 2.4924 (14.5); 2.0737 (3.4); 1.7815 (0.3); 1.7646 (0.9); 1.7450 (1.0); 1.7281 (0.5); 1.7170(0.5); 1.7031 (0.6); 1.6909 (0.6); 1.6786 (0.6); 0.0080 (0.4); -0.0002 (13.6); −0.0085 (0.4) I-02 [00028] .sup.1H NMR(400.2 MHz, d.sub.6-DMSO): δ = 8.3147 (0.3); 8.0607 (13.6); 8.0544 (14.1); 7.8164 (6.1); 7.8099 (5.7); 7.7950 (9.0); 7.7885 (8.9); 7.7145 (16.0); 7.6931 (10.6); 5.7550 (2.7); 3.8021 (2.3); 3.7901 (3.6); 3.7814 (4.8); 3.7729 (3.4); 3.7702 (3.0); 3.7608 (2.6); 3.5740 (0.3); 3.4267 (0.5); 3.3791 (0.5); 3.2708 (0.3); 2.8192 (1.0); 2.8106 (1.3); 2.8022 (1.9); 2.7936 (2.4); 2.7851 (2.3); 2.7764 (2.6); 2.7676 (2.0); 2.7593 (1.4); 2.7505 (1.1); 2.7421 (0.4); 2.7327 (0.4); 2.6754 (0.7); 2.6708 (1.0); 2.6662 (0.7); 2.6616 (0.4); 2.5243 (2.6); 2.5196 (3.8); 2.5109 (50.3); 2.5064 (103.8); 2.5019 (137.8); 2.4972 (98.8); 2.4927 (46.8); 2.3333 (0.6); 2.3287 (0.9); 2.3241 (0.6); 2.0741 (13.4); 1.7832 (1.6); 1.7662 (4.3); 1.7467 (4.5); 1.7297 (2.2); 1.7159 (2.1); 1.7026 (2.5); 1.6895 (2.8); 1.6775 (2.6); 1.6613 (1.3); −0.0002 (5.8) I-03 [00029] .sup.1H NMR(400.2 MHz, d.sub.6-DMSO): δ = 12.3722 (0.4); 8.0087 (1.9); 8.0061 (2.1); 7.9889 (2.1); 7.9862 (2.2); 7.5835 (0.8); 7.5807 (0.8); 7.5649 (1.9); 7.5620 (2.0); 7.5462 (1.2); 7.5433 (1.3); 7.4485 (1.2); 7.4290 (2.0); 7.4102 (0.9); 7.3887 (2.2); 7.3699 (1.8); 3.7930 (0.8); 3.7812 (1.2); 3.7724 (1.6); 3.7638 (1.1); 3.7518 (0.8); 3.3263 (36.1); 2.8018 (0.4); 2.7932 (0.4); 2.7848 (0.6); 2.7761 (0.8); 2.7676 (0.8); 2.7590 (0.9); 2.7500 (0.7); 2.7419 (0.5); 2.7330 (0.4); 2.6750 (0.4); 2.6705 (0.6); 2.6660 (0.4); 2.5883 (16.0); 2.5240 (1.6); 2.5191 (2.4); 2.5105 (31.2); 2.5061 (63.7); 2.5016 (84.6); 2.4970 (61.4); 2.4925 (29.8); 2.3329 (0.4); 2.3284 (0.5); 2.3239 (0.4); 2.0737 (1.5); 1.7753 (0.6); 1.7583 (1.5); 1.7388 (1.6); 1.7219 (0.7); 1.6997 (0.7); 1.6864 (0.9); 1.6731 (1.0); 1.6613 (0.9); 1.6452 (0.4); −0.0001 (2.7) I-04 [00030] .sup.1H NMR(400.2 MHz, d.sub.6-DMSO): δ = 7.7093 (0.4); 7.6219 (0.3); 7.6143 (0.3); 7.5563 (6.0); 7.5479 (9.9); 7.5253 (6.9); 7.2682 (3.2); 7.2605 (3.1); 7.2461 (2.8); 7.2385 (2.7); 4.1379 (2.0); 4.1206 (6.6); 4.1031 (6.6); 4.0858 (2.0); 3.8484 (1.8); 3.8038 (1.1); 3.7919 (1.7); 3.7833 (2.2); 3.7748 (1.6); 3.7626 (1.2); 3.3378 (3.4); 2.8217 (0.5); 2.8127 (0.6); 2.8045 (0.9); 2.7959 (1.2); 2.7874 (1.1); 2.7788 (1.2); 2.7699 (0.9); 2.7617 (0.7); 2.7528 (0.5); 2.6707 (0.4); 2.5242 (1.1); 2.5194 (1.5); 2.5107 (22.9); 2.5063 (47.4); 2.5017 (63.2); 2.4971 (45.8); 2.4926 (22.2); 2.3285 (0.4); 2.0738 (1.2); 1.7819 (0.7); 1.7648 (2.1); 1.7453 (2.2); 1.7283 (1.1); 1.7168 (1.0); 1.7034 (1.2); 1.6905 (1.3); 1.6785 (1.3); 1.6624 (0.6); 1.3764 (7.4); 1.3591 (16.0); 1.3417 (7.2); −0.0002 (2.6) I-05 [00031] .sup.1H NMR(400.2 MHz, d.sub.6-DMSO): δ = 7.7303 (2.6); 7.7084 (2.9); 7.6209 (3.0); 7.6132 (3.1); 7.2065 (1.4); 7.1987 (1.4); 7.1845 (1.3); 7.1768 (1.3); 3.8480 (16.0); 3.8074 (0.5); 3.7955 (0.8); 3.7868 (1.0); 3.7784 (0.7); 3.7756 (0.6); 3.7662 (0.5); 3.3335 (9.4); 2.8093 (0.4); 2.8007 (0.5); 2.7922 (0.5); 2.7836 (0.6); 2.7747 (0.4); 2.6706 (0.4); 2.5241 (1.2); 2.5194 (1.9); 2.5108 (20.5); 2.5063 (42.0); 2.5017 (55.6); 2.4971 (40.3); 2.4926 (19.3); 2.3285 (0.3); 2.0737 (1.0); 1.7824 (0.3); 1.7655 (0.9); 1.7459 (1.0); 1.7291 (0.5); 1.7191 (0.5); 1.7060(0.6); 1.6923 (0.6); 1.6803 (0.6); −0.0002 (2.0) I-06 [00032] .sup.1H NMR(400.2 MHz, d.sub.6-DMSO): δ = 7.5750 (3.0); 7.5673 (5.4); 7.5453 (2.8); 7.2874 (1.4); 7.2797 (1.4); 7.2653 (1.2); 7.2576 (1.2); 3.8513 (16.0); 3.8140 (0.5); 3.8024 (0.8); 3.7937 (1.0); 3.7847 (0.8); 3.7729 (0.6); 3.3353 (4.6); 2.8117 (0.4); 2.8026 (0.6); 2.7944 (0.5); 2.7857 (0.6); 2.7769 (0.5); 2.7682 (0.3); 2.6706 (0.4); 2.6665 (0.3); 2.5240 (1.2); 2.5102 (25.2); 2.5062 (51.2); 2.5018 (67.4); 2.4973 (48.9); 2.3285 (0.4); 2.0741 (2.3); 1.7813 (0.4); 1.7642 (1.0); 1.7453 (1.1); 1.7282 (0.5); 1.7137 (0.5); 1.7001 (0.6); 1.6874 (0.7); 1.6748 (0.6); 0.0079 (0.6); −0.0002 (16.0); −0.0085 (0.5) I-07 [00033] .sup.1H NMR(400.2 MHz, d.sub.6-DMSO): δ = 8.3099 (0.4); 8.3046 (0.4); 7.7336 (2.6); 7.7117 (2.9); 7.6205 (3.0); 7.6127 (3.1); 7.2090 (1.5); 7.2013 (1.4); 7.1870 (1.4); 7.1792 (1.3); 3.8479 (16.0); 3.8187 (0.5); 3.8072 (0.9); 3.7984 (1.1); 3.7890 (0.8); 3.7777 (0.6); 3.3419 (3.4); 2.8167 (0.4); 2.8076 (0.6); 2.7994 (0.6); 2.7908 (0.6); 2.7821 (0.5); 2.7735 (0.4); 2.6705 (0.3); 2.5242 (0.9); 2.5062 (42.0); 2.5018 (55.4); 2.4974 (39.9); 2.3286 (0.3); 2.0742 (1.0); 1.7830 (0.4); 1.7662 (1.0); 1.7471 (1.1); 1.7297 (0.6); 1.7168 (0.6); 1.7028 (0.7); 1.6899 (0.7); 1.6781 (0.7); 0.0079 (0.5); −0.0002 (13.4); −0.0085 (0.4) I-08 [00034] .sup.1H NMR(400.2 MHz, d.sub.6-DMSO): δ = 12.3529 (0.4); 8.0050 (2.1); 7.9862 (2.2); 7.5799 (0.8); 7.5610 (1.8); 7.5432 (1.2); 7.4464 (1.2); 7.4273 (2.0); 7.4080 (0.9); 7.3874 (2.1); 7.3684 (1.8); 3.8024 (0.7); 3.7909 (1.2); 3.7819 (1.6); 3.7734 (1.3); 3.7616 (0.8); 3.3265 (94.1); 2.8081 (0.4); 2.7992 (0.5); 2.7910 (0.7); 2.7824 (0.9); 2.7740 (0.9); 2.7656 (1.0); 2.7568 (0.7); 2.7480 (0.6); 2.7398 (0.4); 2.6744 (0.8); 2.6703 (1.0); 2.6658 (0.8); 2.5885 (16.0); 2.5055 (130.6); 2.5013 (166.7); 2.4969 (123.0); 2.3325 (0.7); 2.3280 (1.0); 2.3238 (0.7); 1.7748 (0.6); 1.7578 (1.6); 1.7388 (1.6); 1.7218 (0.8); 1.6962 (0.7); 1.6830 (1.0); 1.6691 (1.1); 1.6579 (1.0); 1.6420 (0.5); −0.0004 (26.0); −0.0084 (1.5) I-09 [00035] .sup.1H NMR(400.2 MHz, d.sub.6-DMSO): δ = 8.3155 (0.7); 7.5530 (6.2); 7.5451 (8.2); 7.5215 (4.5); 7.2626 (2.2); 7.2550 (2.1); 7.2407 (2.0); 7.2329 (1.8); 4.1357 (1.9); 4.1184 (6.3); 4.1010 (6.3); 4.0837 (1.9); 3.8126 (1.0); 3.8007 (1.5); 3.7921 (2.0); 3.7835 (1.5); 3.7714 (1.1); 3.3298 (71.8); 2.8266 (0.5); 2.8181 (0.6); 2.8098 (0.8); 2.8007 (1.1); 2.7925 (1.0); 2.7841 (1.2); 2.7749 (0.9); 2.7670 (0.7); 2.7583 (0.5); 2.6797 (0.8); 2.6752 (1.7); 2.6706 (2.4); 2.6661 (1.8); 2.6615 (0.9); 2.5782 (0.4); 2.5241 (6.6); 2.5194 (9.7); 2.5107 (139.1); 2.5062 (292.3); 2.5017 (389.5); 2.4971 (275.2); 2.4925 (128.3); 2.3377 (0.7); 2.3331 (1.6); 2.3285 (2.3); 2.3238 (1.6); 2.3195 (0.7); 1.7803 (0.7); 1.7637 (1.9); 1.7443 (2.0); 1.7277 (1.0); 1.7122 (0.9); 1.6992 (1.1); 1.6860 (1.3); 1.6737 (1.2); 1.6582 (0.6); 1.3754 (7.3); 1.3581 (16.0); 1.3406(7.1); 1.3302 (0.8); 1.3125 (0.4); 0.1458 (0.3); 0.0080 (2.6); −0.0002 (91.2); −0.0085 (2.8); −0.1496 (0.4) I-10 [00036] .sup.1H NMR(400.2 MHz, d.sub.6-DMSO): δ = 8.3145 (0.4); 7.6282 (15.0); 7.6205 (16.0); 7.6087 (12.9); 7.5962 (0.5); 7.5866 (15.6); 7.3827 (7.6); 7.3750 (7.2); 7.3606 (6.3); 7.3528 (6.0); 6.5638 (1.3); 6.5555 (2.6); 6.5471 (1.2); 6.4283 (2.8); 6.4199 (5.9); 6.4115 (2.8); 6.2926 (1.3); 6.2843 (2.9); 6.2759 (1.4); 4.4893 (4.1); 4.4810 (4.5); 4.4526 (9.3); 4.4442 (9.1); 4.4159 (4.7); 4.4075 (4.4); 3.8132 (2.4); 3.8013 (3.9); 3.7926 (5.1); 3.7841 (3.7); 3.7815 (3.4); 3.7720 (2.8); 3.3396 (5.6); 2.8276 (1.1); 2.8187 (1.4); 2.8106 (2.0); 2.8019 (2.7); 2.7935 (2.5); 2.7848 (2.8); 2.7759 (2.2); 2.7678 (1.6); 2.7590 (1.2); 2.7505 (0.4); 2.7415 (0.4); 2.6794 (0.5); 2.6751 (1.0); 2.6705 (1.4); 2.6659 (1.0); 2.6616 (0.5); 2.5240 (4.1); 2.5193 (6.1); 2.5106 (82.2); 2.5061 (169.9); 2.5016 (224.8); 2.4970 (160.1); 2.4924 (75.9); 2.3375 (0.4); 2.3329 (1.0); 2.3284 (1.4); 2.3238 (1.0); 2.3193 (0.4); 2.0737 (6.3); 1.7819 (1.7); 1.7649 (4.7); 1.7456 (5.0); 1.7287 (2.4); 1.7146 (2.3); 1.7011 (2.8); 1.6880 (3.1); 1.6764 (2.9); 1.6603 (1.4); 0.1458 (0.5); 0.0080 (3.6); −0.0002 (121.0); −0.0085 (3.9); −0.1497 (0.5) I-11 [00037] .sup.1H NMR(400.2 MHz, d6-DMSO): δ = 8.3147 (0.4); 7.6287 (14.9); 7.6210 (15.8); 7.6080 (13.2); 7.5859 (16.0); 7.3831 (7.6); 7.3754 (7.2); 7.3610 (6.3); 7.3532 (6.1); 6.5643 (1.4); 6.5560 (2.7); 6.5477 (1.2); 6.4288 (2.9); 6.4204 (6.1); 6.4120 (2.8); 6.2933 (1.3); 6.2849 (3.0); 6.2765 (1.4); 4.4901 (4.2); 4.4818 (4.5); 4.4535 (9.4); 4.4451 (9.2); 4.4167 (4.8); 4.4083 (4.5); 3.8032 (2.6); 3.7912 (4.1); 3.7826 (5.3); 3.7741 (3.8); 3.7712 (3.4); 3.7620 (2.8); 3.3469 (4.0); 2.8216 (1.1); 2.8127 (1.4); 2.8045 (2.0); 2.7958 (2.7); 2.7873 (2.5); 2.7787 (2.9); 2.7699 (2.2); 2.7614 (1.6); 2.7527 (1.2); 2.7445 (0.4); 2.7350 (0.3); 2.6796 (0.4); 2.6751 (1.0); 2.6704 (1.3); 2.6659 (1.0); 2.6612 (0.5); 2.5239 (3.8); 2.5192 (5.8); 2.5105 (80.3); 2.5060 (166.1); 2.5015 (220.3); 2.4968 (158.4); 2.4923 (75.8); 2.3374 (0.5); 2.3328 (1.0); 2.3283 (1.4); 2.3237 (1.0); 2.0737 (4.2); 1.7820 (1.7); 1.7649 (4.8); 1.7455 (5.1); 1.7286 (2.5); 1.7168 (2.4); 1.7034 (2.9); 1.6905 (3.2); 1.6785 (3.0); 1.6623 (1.5); 0.1458 (0.5); 0.0080 (4.4); −0.0002 (138.1); −0.0085 (4.5); −0.1496 (0.5) I-12 [00038] .sup.1H NMR(400.2 MHz, d.sub.6-DMSO): δ = 7.5751 (3.0); 7.5658 (3.9); 7.5430 (2.9); 7.2865 (1.5); 7.2788 (1.4); 7.2644 (1.3); 7.2568 (1.2); 3.8493 (16.0); 3.7974 (0.6); 3.7857 (0.9); 3.7771 (1.2); 3.7687 (0.8); 3.7564 (0.6); 3.3444 (1.2); 2.8122 (0.3); 2.8037 (0.5); 2.7951 (0.6); 2.7868 (0.6); 2.7781 (0.6); 2.7692 (0.5); 2.7609 (0.4); 2.6747 (0.4); 2.6702 (0.5); 2.6658 (0.4); 2.5059 (59.4); 2.5014 (76.7); 2.4970 (56.8); 2.3326 (0.3); 2.3283 (0.4); 2.0737 (6.1); 1.7771 (0.4); 1.7599 (1.1); 1.7410 (1.2); 1.7230 (1.0); 1.7079(0.7); 1.6956 (0.7); 1.6832 (0.7); −0.0002 (54.2); −0.0084 (2.4) I-13 [00039] .sup.1H-NMR(400.2 MHz, d.sub.6-DMSO): δ = 8.1352 (6.2); 8.1316 (7.1); 8.1154 (7.0); 8.1118 (7.5); 7.7197 (1.8); 7.7157 (2.0); 7.6993 (5.4); 7.6964 (5.3); 7.6819 (6.2); 7.6780 (6.2); 7.6572 (11.0); 7.6407 (4.7); 7.6375 (3.8); 7.6239 (4.8); 7.6204 (4.3); 7.6040 (6.6); 7.5864 (3.1); 7.5828 (2.9); 3.7951 (0.7); 3.7859 (2.6); 3.7743 (4.0); 3.7655 (4.7); 3.7544 (3.2); 3.7447 (2.0); 3.3514 (2.5); 2.8106 (1.1); 2.8014 (1.5); 2.7932 (2.1); 2.7849 (2.5); 2.7763 (2.4); 2.7678 (2.5); 2.7591 (1.9); 2.7506 (1.4); 2.7420 (1.0); 2.6754 (0.7); 2.6710 (1.0); 2.6665 (0.7); 2.5241 (2.7); 2.5106 (56.6); 2.5064 (114.7); 2.5019 (152.3); 2.4975 (113.7); 2.3333 (0.7); 2.3287 (0.9); 2.3243 (0.7); 2.0743 (16.0); 1.7739 (1.5); 1.7569 (4.7); 1.7379 (5.1); 1.7207 (4.4); 1.7076 (2.9); 1.6945 (3.0); 1.6828 (2.9); 1.6668 (1.3); 0.1460 (0.3); 0.0078 (2.7); −0.0002 (73.8); −0.0080 (2.9); −0.1496 (0.4)

Use Examples

[0505] Meloidouyne incognita Test

[0506] Solvent: 125.0 parts by weight of acetone

[0507] To produce an appropriate active ingredient formulation, 1 part by weight of active ingredient is mixed with the stated amount of solvent and the concentrate is diluted to the desired concentration with water.

[0508] Vessels are filled with sand, active ingredient solution, an egg/larvae suspension of the southern root-knot nematode (Meloidogyne incognita) and lettuce seeds. The lettuce seeds germinate and the plants develop. The galls develop on the roots.

[0509] After 14 days, the nematicidal efficacy in % is determined by the formation of galls. 100% means that no galls were found; 0% means that the number of galls on the treated plants corresponds to the untreated control.

[0510] In this test, for example, the following compounds from the preparation examples show an efficacy of 100% at an application rate of 4 ppm: I-01, 1-02, 1-03, 1-04, I-05, 1-06, 1-07, 1-08, 1-09, 1-10, I-11, 1-12, I-13.

[0511] Meloidogyne incognita Test

[0512] Solvent: 7 parts by weight of dimethylformamide

[0513] Emulsifier: 2.5 parts by weight of alkylaryl polyglycol ether

[0514] To produce a suitable active ingredient formulation, 1 part by weight of active ingredient is mixed with the specified amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, it being necessary to take account of the volume of soil which is drenched. It should be ensured that a concentration of 20 ppm of emulsifier in the soil is not exceeded. To produce further test concentrations, water is used for dilution.

[0515] Pots filled with soil (loamy sand) are watered with the active ingredient solution. An egg/larvae suspension of the southern root-knot nematode (Meloidogyne incognita) is added, lettuce seeds are scattered over the surface of the soil, and they are covered over with quartz sand. The lettuce seeds germinate and the plants develop. The galls develop on the roots.

[0516] After 21 days, the nematicidal efficacy in % is determined by the formation of galls. 100% means that no galls have been found; 0% means that the number of galls on the treated plants corresponds to the untreated control.

[0517] In this test, for example, the following compounds from the preparation examples show an efficacy of 100% at an application rate of 1 ppm: I-01, I-02, I-03, I-04, I-05, I-06, I-07, I-08, I-09.

[0518] In this test, for example, the following compounds from the preparation examples show an efficacy of 80% at an application rate of 1 ppm: I-13.

[0519] In this test, for example, the following compounds from the preparation examples show an efficacy of 100% at an application rate of 0.25 ppm: I-03, I-04, I-05, I-06, I-07, I-08, I-09.

[0520] In this test, for example, the following compounds from the preparation examples show an efficacy of 97% at an application rate of 0.25 ppm: I-01.

[0521] In this test, for example, the following compounds from the preparation examples show an efficacy of 90% at an application rate of 0.25 ppm: I-02.

[0522] In this test, for example, the following compounds from the preparation examples show an efficacy of 100% at an application rate of 0.125 ppm: I-05, I-06, I-07, I-10, I-12.

[0523] In this test, for example, the following compounds from the preparation examples show an efficacy of 98% at an application rate of 0.125 ppm: I-11.

[0524] In this test, for example, the following compounds from the preparation examples show an efficacy of 90% at an application rate of 0.125 ppm: I-01, I-02, I-03, I-04, I-09.

Deposition Examples

[0525] Meloidogyne incognita Test (MELGIN)

[0526] Solvent: 7 parts by weight of dimethylformamide

[0527] Emulsifier: 2.5 parts by weight of alkylaryl polyglycol ether

[0528] To produce a suitable active ingredient formulation, 1 part by weight of active ingredient is mixed with the specified amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration, it being necessary to take account of the volume of soil which is drenched. It should be ensured that a concentration of 20 ppm of emulsifier in the soil is not exceeded. To produce further test concentrations, water is used for dilution.

[0529] Pots filled with soil (loamy sand) are watered with the active ingredient solution. An egg/larvae suspension of the southern root-knot nematode (Meloidogyne incognita) is added, lettuce seeds are scattered over the surface of the soil, and they are covered over with quartz sand. The lettuce seeds germinate and the plants develop. The galls develop on the roots.

[0530] After 21 days, the nematicidal efficacy in % is determined by the formation of galls. 100% means that no galls have been found; 0% means that the number of galls on the treated plants corresponds to the untreated control.

[0531] In this test, for example, the following compounds from the preparation examples show superior efficacy to the prior art: see table 2.

TABLE-US-00002 TABLE 2 Animal Substance Structure species Concentration % Efficacy Ex. I-13 inventive [00040] MELGIN 0.5 ppm 70 Ex. I-440 according to WO2018/083288 [00041] MELGIN 0.5 ppm 0

[0532] Heterodera pallida—Soil Mixing Test (HETDPA)

[0533] Solvent: 4 parts by weight of acetone

[0534] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0535] To produce a suitable preparation of active ingredient, 1 part by weight of active ingredient is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. This active ingredient formulation is mixed with soil (loamy sand). The stated concentration refers to the amount of active ingredient per volume unit of soil (ppm=mg/l).

[0536] 40 cysts of the white potato nematode (Heterodera pallida, 250-275 larvae/cysts) are introduced into 500 ml of this active ingredient soil and mixed. The mixture is introduced into pots and planted in each case with a one-week-old potato seedling (Solanum tuberosum).

[0537] After six weeks, the potato roots are checked for cysts and the average number per pot is calculated as efficacy by the Abbott formula:

[00001]$\mathrm{Efficacy}\%=\left(1-\frac{\mathrm{number}\mathrm{in}B\mathrm{after}\mathrm{treatment}}{\mathrm{number}\mathrm{in}K\mathrm{after}\mathrm{treatment}}\right)\times 100$

[0538] B=treated plants

[0539] K=untreated control plants

[0540] In this test, for example, the compound from the preparation examples that follows shows superior efficacy compared to the prior art; see table 3.

TABLE-US-00003 TABLE 3 Animal Substance Structure species Concentration % Efficacy Ex. 1-04 inventive [00042] MELGIN  0.03125 ppm  97 Ex. I-459 according to WO 2018/083288 [00043] MELGIN  0.03125 ppm  10 Ex. I-07 inventive [00044] MELGIN   0.125 ppm  0.0625 ppm  0.03125 ppm 100 100  90 Ex. I-465 according to WO 2018/083288 [00045] MELGIN   0.125 ppm  0.0625 ppm  0.03125 ppm  95  25  0 Ex. I-06 inventive [00046] MELGIN  0.03125 ppm 0.015625 ppm  92.5*  65 Ex. I-01 inventive [00047] MELGIN HETDPA  0.03125 ppm 0.015625 ppm     1 ppm    0.5 ppm   0.25 ppm  95  58.3** 100  90  75 Ex. I-470 according to WO 2018/083288 [00048] MELGIN HETDPA  0.03125 ppm 0.015625 ppm     1 ppm    0.5 ppm   0.25 ppm  48**  0  70  0  0 Ex. I-12 inventive [00049] MELGIN   0.125 ppm 100 Ex. I-440 according to WO 2018/083288 [00050] MELGIN   0.125 ppm  0 *average from 2 test results **average from 3 test results