pyrazole-derived compounds substituted by halogen as pest control agents, pharmaceutical composition

专利摘要:
PIRAZOL DERIVATIVES REPLACED BY HALOGENE AS PEST CONTROL AGENTS The invention relates, inter alia, to the halogen substituted compounds of the general formula (I) in which the radicals A1-A4, T, n, W, Q, R1 and Z1-Z3 have the meanings defined in the description. Also described are processes for the preparation of the compounds of the formula (I) and possible intermediate products for the preparation of these compounds. The compounds according to the invention are particularly suitable for controlling insects, arachnids and nematodes in agriculture and ectoparasites in veterinary medicine. (I)
公开号:BR112015018311B1
申请号:R112015018311-5
申请日:2014-02-03
公开日:2021-01-05
发明作者:Michael Maue；Kerstin Ilg；Anne Décor；Julia Johanna Hahn；Werner Hallenbach；Reiner Fischer；Hans-Georg Schwarz；Ulrich Görgens；Klaus Raming；Johannes Köbberling；Walter Hübsch；Andreas Turberg；Niels LINDNER；Thomas Bretschneider
申请人:Bayer Animal Health Gmbh；
IPC主号:

专利说明:

[001] The present application refers to new compounds substituted with halogen, the processes for their preparation and their use for the control of animal pests, in particular, arthropods and especially insects, arachnids and nematodes.
[002] Certain halogen-substituted compounds are known to have herbicidal action (cf. J. Org. Chem. 1997, 62 (17), 5908-5919, J. Heterocycl. Chem., 1998 35 (6), 1493- 1499, WO 2004/035545, WO 2004/106324, US 2006/069132, WO 2008/029084).
[003] Additionally, certain halogen-substituted compounds are known to have insecticidal action (EP 1911751, WO2012 / 069366, WO2012 / 080376 and WO2012 / 107434).
[004] In addition, certain halogen-substituted compounds are known to have cytokine inhibiting activity (WO 2000/07980).
[005] Modern crop protection compositions have to meet many requirements, for example, regarding effectiveness, persistence and spectrum of action and their possible use. Toxicity issues, the ability to combine with other active compounds or formulation aids play a role, as well as the expense issue that the synthesis of an active compound requires. In addition, resistance may occur. For all these reasons, the search for new crop protection agents can never be considered to have been completed, and there is a constant need for new compounds having properties that, compared to known compounds, are improved, at least as far as respect to individual aspects.
[006] It was an object of the present invention to provide compounds that broaden the spectrum of pesticides in different aspects and / or improve their activity.
[007] Surprisingly, it has now been found that certain halogen-substituted compounds and their N-oxides and salts have biological properties and are particularly suitable for controlling animal pests, and can therefore be used particularly well in the agrochemical field. and in the animal health sector.
[008] Similar compounds are already known from WO 2010/051926.
[009] Halogen-substituted compounds according to the invention are defined by the general formula (I), by:
wherein R1 represents hydrogen, optionally substituted with C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, C3-C7 cycloalkyl, C1-C6 alkylcarbonyl, C1- C6 alkoxycarbonyl, aryl- (C1-C3) -alkyl, heteroaryl - (C1-C3) -alkyl; R1 represents hydrogen, optionally substituted with C1-C6 alkyl, C2-C6 alkenyl, C3-C6 alkynyl, C3-C7 cycloalkyl, C1-C6 alkylcarbon, C1-C6 alkoxycarbonyl, aryl- (C1- C3) -alkyl, heteroaryl- ( C1-C3) -alkyl; chemical groups: A1 represents CR2 or nitrogen; A2 represents CR3 or nitrogen; A3 represents CR4 or nitrogen; and A4 represents CR5 or nitrogen; but where no more than three of the chemical groups A1 to A4 simultaneously represent nitrogen; R2, R3, R4 and R5 independently of each other represent hydrogen, halogen, cyano, nitro, optionally substituted with C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, N-C1-C6-alkoxyimino-C1- C3-alkyl, C1-C6-alkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, N-C1-C6-alkylamino or N, N-di-C1-C6-alkylamino; if none of the A2 and A3 groups represents nitrogen, R3 and R4 together with the carbon atom to which they are attached, they can form a 5- or 6-membered ring containing 0, 1 or 2 nitrogen atoms and / or 0 or 1 oxygen atom and / or 0 or 1 sulfur atom; or if none of the A1 and A2 groups represents nitrogen, R2 and R3, together with the carbon atom to which they are attached, can form a 6-membered ring containing 0, 1 or 2 nitrogen atoms; W represents oxygen or sulfur; Q represents hydrogen, formyl, hydroxyl, amino or one of the groups optionally substituted with alkyl, alkyloxy, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, cycloalkylalkyl, arylalkyl, heteroarylalkyl or represents an N-alkylamino, N-alkylcarbonylamino, N-alkyl, N-alkylcarbonylamino group; ; or Q represents a 6-membered unsaturated carbocycle, which is optionally mono- or polysubstituted by V or a 5- or 6-membered unsaturated heterocyclic ring, which is optionally mono- or polysubstituted by V; or alternatively Q represents a 6-membered unsaturated carbocycle, which is optionally polysubstituted by V or an unsaturated 5 or 6-membered heterocyclic ring, which is optionally polysubstituted by V; wherein in both cases: V represents halogen, cyano, nitro, optionally substituted with alkyl, alkenyl, alkynyl, cycloalkyl, alkoxy, N-alkoxyiminoalkyl, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl, N, N-dialkylamino; T represents one of the 5-membered T1- T7 heteroaromatics listed below, where the link to the main pyrazole group is marked with an asterisk:
wherein R6, independently of one another, represents halogen, cyano, nitro, amino or optionally substituted with C1-C6 alkyl, C1-C6 alkyloxy, C1-C6 alkylcarbonyl, C1-C6 alkylsulfanyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl ; en represents the values of 0-2; Z1 represents optionally substituted with alkyl and cycloalkyl; and Z2 represents hydrogen, halogen, cyano, nitro, amino or optionally substituted with alkyl, alkylcarbonyl, alkylsulfanyl, alkylsulfinyl, alkylsulfonyl; and Z3 represents hydrogen or optionally substituted with alkyl, cycloalkyl, alkenyl, alkynyl, aryl or heteroaryl.
[010] Preferably, the compounds of formula (I) are provided:
but where no more than three of the chemical groups A1 to A4 simultaneously represent nitrogen; R2, R3, R4 and R5 independently of each other represent hydrogen, halogen, cyano, nitro, optionally substituted with C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, N-alkoxyiminoalkyl, C1- C6 alkylsulfinyl, alkylsulfinyl C1-C6, C1-C6 alkylsulfonyl, N-C1-C6-alkylamino, N, N-di-C1-C6-alkylamino; if none of the A2 and A3 groups represents nitrogen, R3 and R4 together with the carbon atom to which they are attached, they can form a 5- or 6-membered ring containing 0, 1 or 2 nitrogen atoms and / or 0 or 1 oxygen atom and / or 0 or 1 sulfur atom; or if none of the A1 and A2 groups represents nitrogen, R2 and R3, together with the carbon atom to which they are attached, can form a 6-membered ring containing atoms of 0, 1 or 2 nitrogen atoms; W represents oxygen or sulfur; Q represents hydrogen, formyl, hydroxy, amino or one of the optionally substituted C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, C3-C6 cycloalkyl, C1-C5 heterocycloalkyl, C1-C4 alkoxy, C1-C6-alkyl -C3-C6- cycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, aryl- (C1-C3) -alkyl, heteroaryl- (C1-C3) -alkyl or represents an N-C1-C4-alkylamino group, N-C1-C4-alkylcarbonylamino, N, N-di-C1-C4-alkylamino; or Q represents hydrogen, formyl, hydroxy, amino or one of the optionally substituted C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C2-C5 heterocycloalkyl, C1-C4 alkoxy, C1-C6- alkyl-C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, aryl- (C1-C3) -alkyl, heteroaryl- (C1-C3) -alkyl or represents an N-C1-C4-alkylamino group , N-C1-C4-alkylcarbonylamino, N, N-di-C1-C4-alkylamino; or Q represents a 6-membered unsaturated carbocycle, which is optionally mono- or polysubstituted by V or a 5- or 6-membered unsaturated heterocyclic ring, which is optionally mono- or polysubstituted by V; or alternatively Q represents a 6-membered unsaturated carbocycle, which is optionally polysubstituted by V or a 5- or 6-membered unsaturated heterocyclic ring, which is optionally polysubstituted by V; where in both cases V, independently of one another, represents halogen, cyano, nitro, optionally substituted C1-C6 alkyl, C1-C4 alkenyl, C1-C4 alkynyl, C3-C6 cycloalkyl, C1-C6 alkoxy, N-C1 -C6-alkoxyimino-C1-C3-alkyl, C1-C6-alkylsulfanyl, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, N, N-di- (C1-C6-alkyl) amino; T represents one of the 5-membered T1- T7 heteroaromatics listed below, where the link to the main pyrazole group is marked with an asterisk:
wherein, R6 independently of one another represents halogen, cyano, nitro, amino or optionally substituted by halogen with C1-C6 alkyl, C1-C6 alkyloxy, C1-C6 alkylcarbonyl, C1-C6 alkylsulfanyl, C1-C6 alkylsulfinyl, C1-6 alkylsulfonyl C6; en represents the values of 0-1; Z represents optionally substituted with C1-C6 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, and Z represents halogen, cyano, nitro, amino or optionally substituted with C1-C6 alkyl, C1-C6 alkylcarbonyl, C1-C6 alkylsulfinyl, alkylsulfinyl C1-C6, C1-C6 alkylsulfonyl; and Z represents hydrogen or optionally substituted with alkyl, cycloalkyl, alkenyl, alkynyl, aryl or heteroaryl.
[011] Preferably, the compounds of formula (I) are provided:
chemical groups: A1 represents CR2 or nitrogen; A2 represents CR3 or nitrogen; A3 represents CR4 or nitrogen; and A4 represents CR5 or nitrogen; but where no more than three of the chemical groups A1 to A4 simultaneously represent nitrogen; R2, R3, R4 and R5 independently of each other represent hydrogen, halogen, cyano, nitro, optionally substituted C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, N-C1-C6-alkoxyimino-C1-C3 -alkyl, C1-C6 alkylsulfanyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, N-C1-C6-alkylamino or N, N-di-alkyl-C1-C6-amino; W represents oxygen or sulfur; Q represents hydrogen, hydroxy, formyl or one of the C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, C3-C6 cycloalkyl, C2-C5 heterocycloalkyl, C1-C4, C1- C6-alkyl-C3-C6 alkoxy groups -cycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C1-C6-hydroxyalkyl, aryl- (C1-C3) -alkyl, heteroaryl- (C1-C3) - alkyl, N-C1-C4-alkylamino, N -C1-C4-alkylcarbonylamino or N, N-di-C1-C4-alkylamino, which are optionally mono- or polysubstituted, independently of each other, by hydroxy, nitro, amino, halogen, alkoxy, cyano, hydroxycarbonyl, alkoxycarbonyl, alkylcarbamoyl , cycloalkylcarbamoyl, phenyl; or Q represents an aryl group substituted by 0-4 substituents for V or a heteroaromatic with 5 or 6 members substituted with 0-4 substituents for V; where V, independently of one another, represents halogen, cyano, nitro, optionally substituted with C1-C6 alkyl, C1-C4 alkenyl, C1-C4 alkynyl, C3-C6 cycloalkyl, C1-C6 alkoxy, N-C1-C6-alkoxy -imino-C1-C3-alkyl, C1-C6 alkylsulfanyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, N, N-di- (C1-C6-alkyl) amino; T represents one of the 5-membered T1- T7 heteroaromatics listed below, where the link to the main pyrazole group is marked with an asterisk:
wherein: R6 independently of one another represents halogen, cyano, nitro, amino or optionally halogen substituted by C1-C6 alkyl, C1-C6 alkyloxy, C1-C6 alkylcarbonyl, C1-C6 alkylsulfanyl, C1-C6 alkylsulfinyl, C1-6 alkylsulfonyl C6; en represents the values of 0-1; Z1 represents optionally substituted with C1-C6 haloalkyl, C3-C6 cycloalkyl C3-C6 halocycloalkyl; and Z2 represents hydrogen, halogen, cyano, nitro, amino or optionally mono- or polysubstituted with C1-C6 alkyl, C1-C6 alkylcarbonyl, C1-C6 alkylsulfanyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl; and Z3 represents hydrogen or optionally substituted with C1-C6 alkyl, C3-C6 cycloalkyl, C1-C4 alkenyl, C1-C4 alkynyl, aryl and heteroaryl.
[012] Preferably, compounds from
wherein R1 represents hydrogen or represents C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, C3-C7 cycloalkyl, C3-C7-cycloalkyl-C1-C3-alkyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, aryl - (C1-C3) -alkyl, heteroaryl- (C1- C3) -alkyl, which are optionally mono- or pentasubstituted independently of one another by halogen, cyano, alkoxy and alkoxycarbonyl; chemical groups: A1 represents CR2 or nitrogen; A2 represents CR3 or nitrogen; A3 represents CR4 or nitrogen; and A4 represents CR5 or nitrogen; but where no more than three of the chemical groups A1 to A4 simultaneously represent nitrogen; R2, R3, R4 and R5 independently of each other represent hydrogen, halogen, cyano, nitro, or represent C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkoxy, N-C1-C6-alkoxyimino-C1-C3 -alkyl, C1-C6 alkylsulfanyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, N-C1-C6-alkylamino or N, N-di-C1-C6-alkylamino; which are optionally mono- or pentasubstituted independently of each other by hydroxy, nitro, amino, halogen, alkoxy, cyano, hydroxycarbonyl, alkoxycarbonyl, alkylcarbamoyl, cycloalkylcarbamoyl, phenyl; W represents oxygen or sulfur; Q represents hydrogen, hydroxy, formyl or one of the C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, C3-C6 cycloalkyl, C2-C5 heterocycloalkyl, C1-C4, C1- C6-alkyl-C3-C6 alkoxy groups -cycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C1-C6-hydroxyalkyl, aryl- (C1-C3) -alkyl, heteroaryl- (C1-C3) - alkyl, N-C1-C4-alkylamino, N -C1-C4-alkylcarbonylamino or N, N-di-C1-C4-alkylamino, which are optionally mono- or pentasubstituted, independently of each other, by hydroxy, nitro, amino, halogen, alkoxy, cyano, hydroxycarbonyl, alkoxycarbonyl, alkylcarbamoyl , cycloalkylcarbamoyl, phenyl; or Q represents an aryl group substituted by 0-4 substituents for V or a heteroaromatic with 5 or 6 members substituted with 0-4 substituents for V; where V, independently of one another, represents halogen, cyano, nitro, or represents C1-C6 alkyl, C1-C4 alkenyl, C1-C4 alkynyl, C3-C6 cycloalkyl, C1- C6 alkoxy, N-C1-C6-alkoxy- imino-C1-C3-alkyl, C1-C6 alkylsulfanyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, N, N-di- (C1-C6-alkyl) amino optionally independently of another hydroxy, nitro mono- to penta-substituted , amino, halogen, alkoxy, cyano, hydroxycarbonyl, alkoxycarbonyl, alkylcarbonyl, cycloalkylcarbamoyl, phenyl; T represents one of the 5-membered T1- T7 heteroaromatics listed below, where the link to the main pyrazole group is marked with an asterisk:
where: R6 independently of one another, represents halogen, cyano, nitro, amino or optionally mono to pentahalogen substituted by C1-C6 alkyl, C1- C6 alkyloxy, C1-C6 alkylcarbonyl, C1-C6 alkylsulfanyl, C1-C6 alkylsulfonyl, alkylsulfonyl C1-C6; en represents the values of 0-1; Z1 represents C1-C6 haloalkyl, C3-C6 cycloalkyl C3-C6 halocycloalkyl, optionally mono to pentasubstituted by hydroxy, nitro, amino, halogen, alkoxy, cyano, hydroxycarbonyl, alkoxycarbonyl, alkylcarbamoyl, cycloalkylcarbamoyl, phenyl; and Z2 represents hydrogen, halogen, cyano, nitro, amino or represents C1-C6 alkyl, C1-C6 alkylcarbonyl, C1-C6 alkylsulfanyl, C1-C6 alkylsulfonyl, C1-C6 alkylsulfonyl optionally independently of another mono for pentassubstituted with hydroxy, nitro, amino, halogen, alkoxy, cyano, hydroxycarbonyl, alkoxycarbonyl, alkylcarbamoyl, cycloalkylcarbamoyl, phenyl; and Z3 represents hydrogen or represents C1-C6 alkyl, C3-C6 cycloalkyl, C1-C4 alkenyl, C1-C4 alkynyl, aryl and heteroaryl optionally independently substituted with mono for pentasubstituted with hydroxy, nitro, amino, alkoxy, cyano, hydroxycarbonyl, alkoxycarbonyl , alkylcarbamoyl, cycloalkylcarbamoyl, phenyl.
[013] Preferably, the compounds of formula (I) are provided:
wherein R1 represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, methoxymethyl, ethoxymethyl, propoxymethyl, methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, s-butylcarbonyl, s-butylcarbonyl t-butylcarbonyl, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, s-butoxycarbonyl, t-butoxycarbonyl, cyanomethyl, 2-cyanoethyl, benzyl, 4-methoxybenzyl, pyrid-2-ylmethyl, pyrid-3-ylmethyl, pyrid-3-ylmethyl, pyrid-3 ilmethyl, 4-chloropyrid-3-ylmethyl; chemical groups: A1 represents CR2 or nitrogen; A2 represents CR3 or nitrogen; A3 represents CR4 or nitrogen; and A4 represents CR5 or nitrogen; but where no more than three of the chemical groups A1 to A4 simultaneously represent nitrogen; R2 and R5, independently of each other, represent hydrogen, methyl, fluorine or chlorine; and R3 and R4, independently of each other, represent hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, fluoromethyl, difluoromethyl, chlorodifluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, methoxy, ethoxy, n - propoxy, 1-methylethoxy, fluoromethoxy, difluoromethoxy, chlorodifluoromethoxy, dichlorofluoromethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2,2-difluoroethoxy, pentafluoroethoxy, N-methoxy-iminomethyl, imino) ethyl, methylsulfanyl, trifluoromethylsulfanyl, methylsulfonyl, methylsulfinyl, trifluoromethylsulfonyl, trifluoromethylsulfinyl; W represents oxygen or sulfur; Q represents hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, 1,1-dimethylethyl, 1-methylpropyl, n-butyl, 2-methylpropyl, 2-methylbutyl, hydroxyethyl, 2-hydroxypropyl, cyanomethyl, 2-cyanoethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1-trifluoromethyl-ethyl, 2,2-difluoropropyl, 3,3,3-trifluoropropyl, 2,2-dimethyl-3-fluoropropyl, cyclopropyl, 1-cyanocyclopropyl, 1-methoxycarbonylcyclopropyl, 1- (N-methylcarbamoyl) cyclopropyl, 1- (N-cyclopropylcarbamoyl) cyclopropyl, cyclopropylmethyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-cyclopropylethyl, bis (cyclopropylyl) methyl, 2,2- dimethylcyclopropylmethyl, 2-phenylcyclopropyl, 2,2-dichlorocyclopropyl, trans-2-chlorocyclopropyl, cis-2-chlorocyclopropyl, 2,2-difluorocyclopropyl, trans-2-fluorocyclopropyl, cis-2-fluorocyclopropyl, trans-4-hydroxycyclohexyl, 4-trifluoromethylcyclohexyl, prop-2-enyl, 2-methylprop-2-enyl, prop-2-inyl, 1,1-dimethylbut-2-inyl, 3-chloroprop-2-enyl, 3-fluoroprop-2- enyl, 3,3-dichloroprop-2-enyl, 3,3-dichloro-1,1-dimethylprop-2-en useful, oxetan-3-yl, tietan-3-yl, 1-oxothietan-3-yl, 1,1-dioxidotietan-3-yl, isoxazol-3-ylmethyl, 1,2,4-triazol-3-ylmethyl, 3-methyloxetan-3-ylmethyl, benzyl, 2,6-difluorophenylmethyl, 3-fluorophenylmethyl, 2-fluorophenylmethyl, 2,5-difluorophenylmethyl, 1-phenylethyl, 4-chlorophenylethyl, 2-trifluoromethylphenylethyl, 1-pyridin-2-ylethyl, pyridin-2-ylmethyl, 5-fluoropyridin-2-ylmethyl, (6-chloropyridin-3-yl) methyl, pyrimidin-2-ylmethyl, methoxy, 2-ethoxyethyl, 2-methoxyethyl, 2- (methylsulfanyl) ethyl, 1- methyl-2- (ethylsulfanyl) ethyl, 2-methyl-1- (methylsulfanyl) propan-2-yl, methoxycarbonyl, methoxycarbonylmethyl, NH2, N-ethylamino, N-allylamino, N, N-dimethylamino, N, N-diethylamino; or Q represents phenyl, naphthyl, pyridazine, pyrazine, pyrimidine, triazine, pyridine, pyrazole, thiazole, isothiazole, oxazole, isoxazole, triazole, imidazole, furan, thiophene, pyrrole, oxadiazole, thiadiazole replaced by 0, 1, 2, 3 or 3 4 substituents of V; where V, independently of each other, represents fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, difluoromethyl, trichloromethyl, chlorodifluoromethyl, dichlorofluoromethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,2,2,2-tetrafluoroethyl, 1-chloro-1,2,2,2-tetrafluoroethyl, 2,2,2-trichloroethyl, 2-chloro-2,2-difluoroethyl, 1,1-difluoroethyl, pentafluoroethyl, heptafluoro-n-propyl, heptafluoroisopropyl, nonafluoro-n-butyl, cyclopropyl, cyclobutyl, methoxy, ethoxy, n-propoxy, 1-methylethoxy, fluoromethoxy, difluoromethoxy, chlorodifluoromethoxy, dichloro 2,2-trifluoroethoxy, 2-chloro-2,2-difluoroethoxy, pentafluoroethoxy, N-methoxyiminomethyl, 1- (N-methoxyimino) ethyl, methylsulfanyl, methylsulfonyl, methylsulfinyl, trifluoromethylsulfonyl, dimethylamino; T represents one of the 5-membered T1- T7 heteroaromatics listed below, where the link to the main pyrazole group is marked with an asterisk:
wherein, R6, independently of one another, represents halogen, cyano, nitro, amino, methyl, ethyl, 1-methylethyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, trifluoromethoxy, 2,2-difluoroethoxy, 2,2 , 2-trifluoroethoxy, ethylcarbonyl, trifluoromethylcarbonyl, methylsulfanyl, methylsulfinyl, methylsulfonyl, trifluoromethylsulfinyl; en represents the values of 0-1; Z1 represents a methyl, ethyl, 1,1-dimethylethyl, difluoromethyl, trichloromethyl, chlorodifluoromethyl, dichlorofluoromethyl, trifluoromethyl, bromodichloromethyl, 1-fluoroethyl, 1-fluoro-1-methylethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2, 2,2-trifluoroethyl, 1,2,2,2-tetrafluoroethyl, 1-chloro-1,2,2,2-tetrafluoroethyl, 2,2,2-trichlorethyl, 2-chloro-2,2-difluoroethyl, 1, 1-difluoroethyl, pentafluoroethyl, heptafluoro-n-propyl, heptafluoroisopropyl, nonafluoro-n-butyl, cyclopropyl, 1-chlorocyclopropyl, 1-fluoro-cyclopropyl, 1-bromocyclopropyl, 1-cyanocyclopropyl, 1-trifluoromethyl-cyclo-fluoro-methyl 1-methylcyclopropyl; and Z2 represents hydrogen, halogen, cyano, nitro, amino, methyl, ethyl, 1,1-dimethylethyl, difluoromethyl, trichloromethyl, chlorodifluoromethyl, dichlorofluoromethyl, trifluoromethyl, bromodichloromethyl, 1-fluoroethyl, 1-fluoro-1-methylethyl, 2-fluoro , 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,2,2,2-tetrafluorethyl, 1-chloro-1,2,2,2-tetrafluoroethyl, 2,2,2-trichlorethyl, 2-chlorine -2,2- difluoroethyl, 1,1-difluoroethyl, pentafluoroethyl, heptafluoro-n-propyl, heptafluoroisopropyl, nonafluoro-n-butyl, methylsulfanyl, methylsulfinyl, methylsulfonyl, ethylthio, ethylsulfinyl, ethylsulfonyl, trifluoromethyl, trifluoromethyl, trifluoromethyl , chlorodifluoromethylsulfonyl, dichlorofluoromethylsulfanyl, dichlorofluoromethylsulfinyl, and dichlorofluoromethylsulfonyl; Z3 represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, ethylenyl, 1-propenyl, 2-propenyl, 1-propynyl, 1-butynyl, difluoromethyl, trichloromethyl, chlorodifluoromethyl, dichlorofluoromethyl, trifluoromethyl, 1-fluoroethyl, 1-fluoro-1-methylethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, phenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,5-dichlorophenyl, 3,4-dichlorophenyl, 2,6-dichlorophenyl, 2,6-dichloro-4-trifluoromethylphenyl, 3-chloro-5-trifluoromethylpyridin-2-yl.
[014] Preferably, the compounds of formula (I) are provided, in which: Z1 represents trifluoromethyl, 1-chlorocyclopropyl, 1-fluorocyclopropyl, or pentafluoroethyl; Z2 represents trifluoromethyl, nitro, methylsulfanyl, methylsulfinyl, methylsulfonyl, fluorine, chlorine, bromine, cyano or iodine; Z3 represents methyl, ethyl, n-propyl or hydrogen; R1 represents hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, methoxymethyl, ethoxymethyl, propoxymethyl, methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, s-butylcarbonyl, t-butylcarbonyl, t-butylcarbonyl butylcarbonyl, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, s-butoxycarbonyl, t-butoxycarbonyl, cyanomethyl, 2-cyanoethyl, benzyl, 4-methoxybenzyl, pyrid-2-ylmethyl, pyrid-3-ylmethyl, pyrid-4-ylmethyl, pyrid-4-ylmethyl 4-chloropyrid-3-ylmethyl; A1 and A4 each represent CH; A2 represents CH or N; A3 represents CR4; and R4 represents methyl, ethyl, fluorine, chlorine, bromine or iodine; T represents one of the 5-membered T1- T7 heteroaromatics listed below, where the link to the main pyrazole group is marked with an asterisk:
R6 represents hydrogen, methyl, ethyl, 2-methylethyl, 2,2-dimethylethyl, fluorine, chlorine, bromine, iodine, nitro, trifluoromethyl, amino; W represents oxygen; and Q represents hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, 1,1-dimethylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 2-methylbutyl, hydroxymethyl, 2-hydroxypropyl, cyanomethyl, 2-cyanoethyl , 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1-trifluoromethylethyl, 2,2-difluoropropyl, 3,3,3-trifluoropropyl, 2,2-dimethyl-3-fluoropropyl, cyclopropyl, 1 -cyanocyclopropyl, 1-methoxycarbonylcyclopropyl, 1- (N-methylcarbamoyl) cyclopropyl, 1- (N-cyclopropylcarbamoyl) cyclopropyl, cyclopropylmethyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-cyclopropylethyl, bis (cyclopropyl) methyl, 2,2-dimethyl , 2-phenylcyclopropyl, 2,2-dichlorocyclopropyl, trans-2-chlorocyclopropyl, cis-2-chlorocyclopropyl, 2,2-difluorocyclopropyl, trans-2-fluorocyclopropyl, cis-2-fluorocyclopropyl, trans-4-hydroxycyclohexyl, 4 - trifluoromethylcyclohexyl, prop-2-enyl, 2-methylprop-2-enyl, prop-2-inyl, 1,1-dimethylbut-2-inyl, 3-chloroprop-2-enyl, 3,3-dichloroprop-2 -enyl, 3,3-dichloro-1,1-dimethylprop-2-enyl, phenyl, 2-chlorophen useful, 3-chlorophenyl, 4-chlorophenyl, oxetan-3-yl, tietan-3-yl, 1-oxidotietan-3-yl, 1,1-dioxidotietan-3-yl, isoxazol-3-ylmethyl, 1,2, 4-triazol-3-ylmethyl, 3-methyloxetan-3-ylmethyl, benzyl, 2,6-difluorophenylmethyl, 3-fluorophenylmethyl, 2-fluorophenylmethyl, 2,5-difluorophenylmethyl, 1-phenylethyl, 4-chlorophenylethyl, 2-trifluorethylphenylethyl, 1-pyridin-2-ylethyl, pyridin-2-ylmethyl, (6-chloropyridin-3-yl) methyl, 5-fluoropyridin-2-ylmethyl, pyrimidin-2-ylmethyl, methoxy, 2-ethoxyethyl, 2- (methylsulfanyl) ethyl, 1-methyl-2- (ethylsulfanyl) ethyl, 2-methyl- 1- (methylsulfanyl) propan-2-yl, methoxycarbonyl, methoxycarbonylmethyl, NH2, N-ethylamino, N-allylamino, N, N-dimethylamino, N, N-diethylamino; or alternatively Q represents hydrogen, methyl, ethyl, n-propyl, 1-methylethyl, 1,1-dimethylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 2-methylbutyl, hydroxyethyl, 2-hydroxypropyl, cyanomethyl, 2- cyanoethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1-trifluoromethylethyl, 2,2-difluoropropyl, 3,3,3-trifluoropropyl, 2,2-dimethyl-3-fluoropropyl, cyclopropyl, 1-cyanocyclopropyl, 1-methoxycarbonylcyclopropyl, 1- (N-methylcarbamoyl) cyclopropyl, 1-carbamoylcyclopropyl, 1-carbamothiocyclopropyl, 1- (N-cyclopropylcarbamoyl) cyclopropyl, cyclopropylmethyl, cyclobutyl, cyclopentyl, cyclopropyl, cyclohexyl cyclopropyl) methyl, 2,2-dimethylcyclopropylmethyl, 2-phenylcyclopropyl, 2,2-dichlorocyclopropyl, trans-2-chlorocyclopropyl, cis-2-chlorocyclopropyl, 2,2-difluorocyclopropyl, trans-2-fluorocyclopropyl, cis-2-fluorocyclopropyl, trans-4-hydroxycyclohexyl, 4-trifluoromethylcyclohexyl, prop-2-enyl, 2-methylprop-2-enyl, prop-2-inyl, 1,1-dimethylbut-2-inyl, 3-chloroprop-2- enil, 3,3-dichlor oprop-2-enyl, 3,3-dichloro-1,1-dimethylprop-2-enyl, oxetan-3-yl, tietan-3-yl, 1-oxidotietan-3-yl, 1,1-detoxotietan-3- yl, isoxazol-3-ylmethyl, 1,2,4-triazol-3-ylmethyl, 3-methyloxetan-3-ylmethyl, benzyl, 2,6-difluorophenylmethyl, 3-fluorophenylmethyl, 2-fluorophenylmethyl, 2,5-difluorophenylmethyl, 1-phenylethyl, 4-chlorophenylethyl, 2-trifluormethylphenylethyl, 1-pyridin-2-ylethyl, pyridin-2-ylmethyl, (6-chloropyridin-3-yl) methyl, 5-fluoropyridin-2-ylmethyl, pyrimidin-2-ylmethyl , methoxy, 2-ethoxyethyl, 2- (methylsulfanyl) ethyl, 1-methyl-2- (ethylsulfanyl) ethyl, 2-methyl- 1- (methylsulfanyl) propan-2-yl, methoxycarbonyl, methoxycarbonylmethyl, NH2, N-ethylamino, N-allylamino, N, N-dimethylamino, N, N-diethylamino; Q represents phenyl, naphthyl, pyridazine, pyrazine, pyrimidine, triazine, pyridine, pyrazole, thiazole, isothiazole, oxazole, isoxazole, triazole, imidazole, furan, thiophene, pyrrole, oxadiazole, thiadiazole substituted by 0, 1, 2, or 3 substituted of V; where V, independently of each other, represents fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, difluoromethyl, trichloromethyl, chlorodifluoromethyl, dichlorofluoromethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,2,2,2-tetrafluoroethyl, 1-chloro-1,2,2,2-tetrafluoroethyl, 2,2,2-trichloroethyl, 2-chloro-2,2-difluoroethyl, 1,1-difluoroethyl, pentafluoroethyl, heptafluoro-n-propyl, heptafluoroisopropyl, nonafluoro-n-butyl, cyclopropyl, cyclobutyl, methoxy, ethoxy, n-propoxy, 1-methylethoxy, fluoromethoxy, difluoromethoxy, chlorodifluoromethoxy, dichloro 2,2-trifluoroethoxy, 2-chloro-2,2-difluoroethoxy, pentafluoroethoxy, N-methoxyiminomethyl, 1- (N-methoxyimino) ethyl, methylsulfanyl, methylsulfonyl, methylsulfinyl, trifluoromethylsulfonyl, trifluoromethylsulfinyl, trifluoromethylsulfinyl, trifluoromethyl - dimethylamino.
[015] Very especially preferred are, in addition, the compounds in each case, defined by one of the general formulas I (a), I (b), I (c), I (d), I (e), I (f ), I (g), where the radicals A1-A4, n, W, Q, R1 and Z1-Z3 have the general, preferred or particularly preferred meanings described above.


[016] Especially preferred are all compounds of general formula (Ic), in which the preferred bands 1234 16 1 for the radicals A, A, A, A, Q, R, R, W, Z, Z2 and Z3 apply. corresponding to the above preferred ranges for the compounds of the general formula (I).
[017] Very particular preference is given alternatively to the compounds of the general formula (Ia), where Z1 represents CF2CF3, Z2 represents CF3, Z3 represents CH3, the radicals R1, R6a, R6b and R6c represent hydrogen, A1, A2, A4 represent CH, A3 represents C-Cl, W represents oxygen and Q represents 1-cyanocyclopropyl or cyclopropyl.
[018] Very particular preference is given alternatively to the compounds of the general formula (Ia), where Z1 represents CF2CF3, Z2 represents CF3, Z3 represents CH3, the radicals R1, R6a, R6b and R6c represent hydrogen, A1, A4 represent CH, A2 represents N, A3 represents C-Cl, W represents oxygen and Q represents 1-cyanocyclopropyl or cyclopropyl.
[019] Very particular preference is also given to compounds of the general formula (Ib) in which Z1 represents CF2CF3, Z2 represents CF3, Z3 represents CH3, the radicals R1, R6a and R6b represent hydrogen, A1, A2, A4 represent CH , A3 represents C-Cl, W represents oxygen and Q represents 1-cyanocyclopropyl or cyclopropyl.
[020] Very particular preference is also given to compounds of the general formula (Ib) in which Z1 represents CF2CF3, Z2 represents CF3, Z3 represents CH3, the radicals R1, R6a, R6b and R6c represent hydrogen, A1, A4 represent CH , A2 represents N, A3 represents C-Cl, W represents oxygen and Q represents 1-cyanocyclopropyl or cyclopropyl.
[021] Very particular preference is also given to compounds of the general formula (Ic) in which Z1 represents CF2CF3, Z2 represents CF3, Z3 represents a methyl, ethyl, phenyl, 4-NO2-phenyl, 3-chloropyridin-2 group - il, the radicals R1, R6a represent hydrogen or methyl, R6b represents hydrogen, methyl or CF3, A1, A4 represent CH, A2 represents CH or CF, A3 represents CH or C-Cl, W represents oxygen and Q represents one of the radicals 1- cyanocyclopropyl, benzyl, cyclopropyl, 2-thienylmethyl, carbamothioylcyclopropyl, pyrid-4-yl, 2,2,2-trifluoroethyl, methylsulfonyl, tietan-3-yl, 1-carbamoylcyclopropyl.
[022] Very particular preference is given alternatively to compounds of the general formula (Ic) in which Z1 represents CF2CF3, Z2 represents CF3, Z3 represents a methyl, ethyl, phenyl, 4-NO2-phenyl, 3-chloropyridin-2-yl group , the radicals R1, R6a represents hydrogen or methyl, R6b represents hydrogen, methyl or CF3, A1, A4 represent CH, A2 represents N, A3 represents CH or C-Cl, W represents oxygen and Q represents one of the radicals 1-cyanocyclopropyl, benzyl, cyclopropyl, 2-thienylmethyl, carbamothioylcyclopropyl, pyrid-4-yl, 2,2,2-trifluoroethyl, methylsulfonyl, tietan-3-yl, 1-carbamoylcyclopropyl.
[023] Very particular preference is also given to compounds of the general formula (Id), where Z1 represents CF2CF3, Z2 represents CF3, Z3 represents CH3, the radicals R1, R6a and R6b represent hydrogen, A1, A2, A4 represents CH, A3 represents C-Cl, W represents oxygen and Q represents 1-cyanocyclopropyl or cyclopropyl.
[024] Very particular preference is alternatively given to compounds of the general formula (Id), where Z1 represents CF2CF3, Z2 represents CF3, Z3 represents CH3, the radicals R1, R6a, R6b and R6c represent hydrogen, A1, A4 represent CH, A2 represents N, A3 represents C-Cl, W represents oxygen and Q represents 1-cyanocyclopropyl or cyclopropyl.
[025] Very particular preference is also given to compounds of the general formula (Ie), where Z1 represents CF2CF3, Z2 represents CF3, Z3 represents CH3, the radicals R1, R6a and R6b represent hydrogen, A1, A2, A4 represent CH, A3 represents C-Cl, W represents oxygen and Q represents one of the radicals 1-cyanocyclopropyl, 2-thienylmethyl, 6-chloropyridin-3-yl, 1-carbamothioylcyclopropyl or cyclopropyl.
[026] Very particular preference is alternatively given to the compounds of the general formula (Ie), where Z1 represents CF2CF3, Z2 represents CF3, Z3 represents CH3, the radicals R1, R6a and R6b represent hydrogen, A1, A4 represents CH, A2 represents N, A3 represents C-Cl, W represents oxygen and Q represents one of the radicals 1-cyanocyclopropyl, 2-thienylmethyl, 6-chloropyridin-3-yl, 1-carbamothioylcyclopropyl or cyclopropyl.
[027] Most preference is given to compounds of the general formula (Ic), where Z1 represents CF2CF3, Z2 represents CF3, Z3 represents methyl, ethyl, phenyl, 4-NO2-phenyl, 3-chloropyridin-2-yl, the radicals R1, R6a represent hydrogen or methyl, R6b represents hydrogen, methyl or CF3, A1, A4 represent CH, A2 represents CH or CF, A3 represents CH or C-Cl, W represents oxygen and Q represents one of the radicals 1-cyanocyclopropyl , benzyl, cyclopropyl, 2-thienylmethyl, carbamothioylcyclopropyl, pyrid-4-yl, 2,2,2-trifluoroethyl, methylsulfonyl, tietan-3-yl, 1-carbamoylcyclopropyl.
[028] Most preference is given as an alternative to compounds of the general formula (Ic), where Z1 represents CF2CF3, Z2 represents CF3, Z3 represents a methyl, ethyl, phenyl, 4-NO2-phenyl, 3-chloropyridin-2 group -il, the radicals R1, R6a represents hydrogen or methyl, R6b represents hydrogen, methyl or CF3, A1, A4 represents CH, A2 represents N, A3 represents CH or C-Cl, W represents oxygen and Q represents one of the radicals 1- cyanocyclopropyl, benzyl, cyclopropyl, 2-thienylmethyl, carbamothioylcyclopropyl, pyrid-4-yl, 2,2,2-trifluoroethyl, methylsulfonyl, tietan-3-yl, 1-carbamoylcyclopropyl.
[029] According to the invention, "alkyl" - either by itself or as part of a chemical group - represents straight or branched chain hydrocarbons, preferably having 1 to 6 carbon atoms, such as, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,2-dimethylpropyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,2-dimethylpropyl, 1,3-dimethylbutyl, 1,4-dimethylbutyl, 2,3- dimethylbutyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethylbutyl and 2-ethylbutyl. Preference is additionally given to alkyl groups having 1 to 4 carbon atoms, such as, inter alia, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl or t-butyl. The alkyl groups according to the invention can be replaced by one or more identical or different radicals.
[030] According to the invention, "alkenyl" - either by itself or as part of a chemical group - represents straight or branched chain hydrocarbons, preferably having 2 to 6 carbon atoms and at least one double bond, such as , for example, vinyl, 2-propenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl- 2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl- 2-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-2-propenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-2-pentenyl, 2-methyl- 2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4- pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-2-butenyl, 1, 2-dimethyl-3-butenyl, 1,3-dimethyl-2-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 1- ethyl -2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2 -propenyl and 1-ethyl-2-methyl-2-propenyl. Preference is given, in addition, to alkenyl groups having 2 to 4 carbon atoms, such as, inter alia, 2-propenyl, 2-butenyl or 1-methyl-2-propenyl. The alkenyl groups according to the invention can be replaced by one or more identical or different radicals.
[031] According to the invention, "alkynyl" - by itself or as part of a chemical group - represents straight or branched chain hydrocarbons, preferably having 2 to 6 carbon atoms and at least one triple bond such as , for example, 2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-3-butynyl, 2-methyl-3- butynyl, 1-methyl-2-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2- pentinyl, 1-methyl-3-pentynyl, 1-methyl-4-pentinyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl, 4-methyl-2-pentinyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl- 1-methyl-2-propynyl and 2,5-hexadiene. Preference is additionally given for alkynyl groups having 2-4 carbon atoms, such as, among others, ethynyl, 2-propynyl or 2-butynyl-2-propenyl. The alkynyl groups according to the invention can be replaced by one or more, identical or different radicals.
[032] According to the invention, "cycloalkyl" - by itself or as part of a chemical group - represents mono-, bi- or tricyclic hydrocarbons, preferably having 3 to 10 carbon atoms, such as, for example , cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, bicyclo [2.2.1] heptyl, bicyclo [2.2.2] octyl or adamantyl. Preference is additionally given for cycloalkyl groups having 3, 4, 5, 6 or 7 carbon atoms, such as, inter alia, cyclopropyl or cyclobutyl. The cycloalkyl groups according to the invention can be replaced by one or more, identical or different radicals.
[033] According to the invention, "alkylcycloalkyl" represents mono-, bi- or tricyclic alkylcycloalkyl, preferably having 4 to 10 or 4 to 7 carbon atoms, such as, for example, ethylcyclopropyl, isopropylcyclobutyl, 3-methylcyclopentyl and 4-methylcyclohexyl. Preference is additionally given for alkylcycloalkyl groups having 4, 5 or 7 carbon atoms, such as, inter alia, ethylcyclopropyl or 4-methylcyclohexyl. The alkylcycloalkyl groups according to the invention can be replaced by one or more identical or different radicals.
[034] According to the invention, "cycloalkylalkyl" represents mono-, bi- or tricyclic, preferably cycloalkylalkyl having 4 to 10 or 4 to 7 carbon atoms, such as, for example, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cycloalkyl hexylmethyl and cyclopentylethyl. Preference is additionally given to cycloalkylalkyl groups having 4, 5 or 7 carbon atoms, such as, inter alia, cyclopropylmethyl or cyclobutylmethyl. The cycloalkylalkyl groups according to the invention can be replaced by one or more identical or different radicals.
[035] According to the invention, "halogen" represents fluorine, chlorine, bromine or iodine, in particular, fluorine, chlorine or bromine.
[036] The halogen-substituted chemical groups according to the invention, such as, for example, haloalkyl, halocycloalkyl, haloalkyloxy, haloalkylsulfanyl, haloalkylsulfinyl haloalkylsulfonyl or are mono- or polysubstituted by halogen to the maximum possible number of substituents. In the case of halogen polysubstitution, the halogen atoms can be the same or different, and can be attached to one or a plurality of carbon atoms. Here, halogen represents, in particular, fluorine, chlorine, bromine or iodine, preferably fluorine, chlorine or bromine, and especially preferably fluorine.
[037] According to the invention, "halocycloalkyl" represents mono-, bi- or tricyclic halocycloalkyl having preferably 3 to 10 carbon atoms, such as, inter alia, 1-fluorocyclopropyl, 2-fluorocyclopropyl, or 1- fluorocyclobutyl. Preference is additionally given for halocycloalkyl having 3, 5 or 7 carbon atoms. The halocycloalkyl groups according to the invention can be replaced by one or more identical or different radicals.
[038] According to the invention, "haloalkyl", "haloalkenyl" or "haloalkynyl" represents halogen substituted by alkyl, alkenyl or alkynyl groups having preferably 1 to 9 equal or different halogen atoms, such as, for example, example, monohaloalkyl, such as CH2CH2Cl, CH2CH2F, CHClCH3, CHFCH3, CH2Cl, CH2F; perhaloalkyl, such as CCl3 or CF3 or CF2CF3; polyhaloalkyl, such as CHF2, CH2F, CH2CHFCl, CHCl2, CF2CF2H, CH2CF3. This applies correspondingly to haloalkenyl and other halogen-substituted radicals. Haloalkoxy is, for example, OCF3, OCHF2, OCH2F, OCF2CF3, OCH2CF3 and OCH2CH2Cl.
[039] Other examples of haloalkyl groups are trichloromethyl, chlorodifluoromethyl, dichlorofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichlorethyl, 2-chloro-2 , 2-difluoroethyl, pentafluoroethyl and pentafluoro-t-butyl. Preference is given to haloalkyl groups having 1 to 4 carbon atoms and 1 to 9, preferably 1 to 5 identical or different halogen atoms selected from the group consisting of fluorine, chlorine and bromine. Particular preference is given to haloalkyl groups having 1 or 2 carbon atoms and 1 to 5 equal or different halogen atoms selected from the group consisting of fluorine and chlorine, such as, inter alia, difluoromethyl, trifluoromethyl or 2,2 -difluoroethyl.
[040] According to the invention, "hydroxyalkyl" represents a straight or branched chain alcohol, preferably having 1 to 6 carbon atoms, such as, for example, methanol, ethanol, n-propanol, isopropanol, n- butanol, isobutanol, s-butanol and t-butanol. In addition, preference is given to hydroxyalkyl groups having 1 to 4 carbon atoms. The hydroxyalkyl groups according to the invention can be replaced by one or more identical or different radicals.
[041] According to the invention, "alkoxy" represents a straight or branched chain O-alkyl, preferably having 1 to 6 carbon atoms, such as, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, s-butoxy and t-butoxy. Preference is additionally given for alkoxy groups having 1 to 4 carbon atoms. The alkoxy groups according to the invention can be replaced by one or more identical or different radicals.
[042] According to the invention, "haloalkoxy" represents halogen substituted by straight-chain or branched O-alkyl having preferably 1 to 6 carbon atoms, such as, inter alia, difluoromethoxy, trifluoromethoxy, 2,2- difluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2,2,2-trifluoroethoxy and 2-chloro-1,1,2-trifluoroethoxy. Preference is additionally given for haloalkoxy groups having 1 to 4 carbon atoms. The haloalkoxy groups according to the invention can be replaced by one or more identical or different radicals.
[043] According to the invention, "alkylsulfanyl" represents a straight or branched chain S-alkyl, preferably having 1 to 6 carbon atoms, such as, for example, methylthio, ethylthio, n-propylthio, isopropylthio , n-butylthio, isobutylthio, s-butylthio and t-butylthio. Preference is additionally given for alkylsulfanyl groups having 1 to 4 carbon atoms. The alkylsulfanyl groups according to the invention can be replaced by one or more identical or different radicals.
[044] Examples of haloalkylsulfanylalkyl groups, i.e. halo-substituted alkylsulfanyl groups, are, inter alia, difluoromethylthio, trifluoromethylthio, trichloromethylthio, chlorodifluoromethylthio, 1-fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethyl, 2-tetrafluoroethylthio, 2,2,2-trifluoroethylthio, or 2-chloro-1,1,2-trifluoroethylthio.
[045] According to the invention, "alkylsulfinyl" represents a straight or branched chain alkylsulfinyl, preferably having from 1 to 6 carbon atoms, such as, for example, methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, isopropylsulfinyl, n - butylsulfinyl, isobutylsulfinyl, s-butylsulfinyl and t-butylsulfinyl. Preference is preferably given to alkylsulfinyl groups having 1 to 4 carbon atoms. The alkylsulfinyl groups according to the invention can be replaced by one or more identical or different radicals.
[046] Examples of haloalkylsulfinyl groups, i.e. halo-substituted alkylsulfinyl groups, are, inter alia difluoromethylsulfinyl, trifluoromethylsulfinyl, trichloromethylsulfinyl, chlorodifluoromethylsulfinyl, 1-fluoroethylsulfinyl, 2-fluoroethylsulfinyl, 2,2-2,2 - tetrafluoroethylsulfinyl, 2,2,2-trifluoroethylsulfinyl and 2-chloro-1,1,2-trifluoroethylsulfinyl.
[047] According to the invention, "alkylsulfonyl" represents a straight or branched chain alkylsulfonyl, preferably having 1 to 6 carbon atoms, such as, for example, methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, isopropylsulfonyl, n- butylsulfonyl, isobutylsulfonyl, s-butylsulfonyl and t-butylsulfonyl. Preference is additionally given for alkylsulfonyl groups having 1 to 4 carbon atoms. The alkylsulfonyl groups according to the invention can be replaced by one or more identical or different radicals.
[048] Examples of haloalkylsulfonyl groups, that is, halogen-substituted alkylsulfonyl groups, are, inter alia, difluoromethylsulfonyl, trifluoromethylsulfonyl, trichloromethylsulfonyl, chlorodifluoromethylsulfonyl, 1-fluoroethylsulfonyl, 2-fluoroethylsulfonyl, 1,1-2,2 2-tetrafluoroethylsulfonyl, 2,2,2-trifluoroethylsulfonyl and 2-chloro-1,1,2-trifluoroethylsulfonyl.
[049] According to the invention, "alkylcarbonyl" represents a straight or branched alkyl-C (= O) chain, preferably having 2 to 7 carbon atoms, such as methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, isopropylcarbonyl, s -butylcarbonyl and t-butylcarbonyl. Preference is additionally given for alkylcarbonyl groups having 1 to 4 carbon atoms. The alkylcarbonyl groups according to the invention can be replaced by one or more identical or different radicals.
[050] According to the invention, "cycloalkylcarbonyl" represents a straight or branched chain cycloalkylcarbonyl, preferably having 3 to 10 carbon atoms in the cycloalkyl portion, such as, for example, cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, cycloalkyl hexylcarbonyl, cycloheptycarbonyl, cyclooctylcarbonyl, bicyclo [2.2.1] heptyl, bicyclo [2.2.2] octycarbonyl and adamantylcarbonyl. Preference is additionally provided for cycloalkylcarbonyl having 3, 5 or 7 carbon atoms in the cycloalkyl portion. The cycloalkylcarbonyl groups according to the invention can be replaced by one or more identical or different radicals.
[051] According to the invention, "alkoxycarbonyl" - alone or as a constituent of a chemical group - represents a straight or branched chain, alkoxycarbonyl, preferably having 1 to 6 carbon atoms or having 1 to 4 atoms of carbon in the alkoxy fraction, such as, for example, methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, s-butoxycarbonyl and t-butoxycarbonyl. The alkoxycarbonyl groups according to the invention can be replaced by one or more identical or different radicals.
[052] According to the invention, "alkylaminocarbonyl" represents a straight or branched chain alkylaminocarbonyl having preferably 1 to 6 carbon atoms or 1 to 4 carbon atoms in the alkyl portion, such as, for example, methylaminocarbonyl , ethylaminocarbonyl, n-propylaminocarbonyl, isopropylaminocarbonyl, s-butylaminocarbonyl and t-butylaminocarbonyl. The alkylaminocarbonyl groups according to the invention can be replaced by one or more identical or different radicals.
[053] According to the invention, "N, N-dialkylaminocarbonyl" represents a straight or branched chain N, N-dialkylaminocarbonyl, preferably having 1 to 6 carbon atoms or 1 to 4 carbon atoms in the radical alkyl, such as, for example, N, N-dimethylaminocarbonyl, N, N-diethylaminocarbonyl, N, N-di (n-propylamino) carbonyl, N, N- di (isopropylamino) carbonyl and N, N-di- (s -butylamino) carbonyl. The N, N-dialkylaminocarbonyl groups according to the invention can be replaced by one or more identical or different radicals.
[054] According to the invention, "aryl" represents a mono-, bi- or polycyclic aromatic system, preferably having from 6 to 14, in particular from 6 to 10 carbon atoms in the ring, such as, for example, phenyl, naphthyl, anthryl, phenanthrenyl, preferably phenyl. In addition, aryl also represents polycyclic systems, such as, tetrahydronaphile, indenyl, indanyl, fluorenyl, biphenylyl, where the binding site is in the aromatic system. The aryl groups according to the invention can be replaced by one or more identical or different radicals.
[055] Examples of substituted aryl groups are arylalkyl groups that can also be replaced by one or more identical or different radicals in the alkyl and / or aryl moiety. Examples of such arylalkyl groups are, inter alia, benzyl and 1-phenylethyl.
[056] According to the invention, "heterocycle", "heterocyclic ring" or "heterocyclic ring system" represents a carbocyclic ring system having at least one ring in which at least one carbon atom is replaced by a hetero atom, preferably, by a heteroatom from the group consisting of N, O, S, P, B, Si, Se, and which is saturated, unsaturated or heteroaromatic and can be unsubstituted or replaced by a Z substituent, where the point fixture is located on a ring atom. Unless defined differently, the heterocyclic ring preferably contains 3 to 9 ring atoms, especially 3 to 6 ring atoms, and one or more, preferably 1 to 4, in particular 1, 2 or 3, hetero atoms in the heterocyclic ring, preferably from the group consisting of N, O, and S, although two oxygen atoms should not be directly adjacent. Heterocyclic rings generally contain no more than 4 nitrogen atoms and / or no more than 2 oxygen atoms and / or no more than 2 sulfur atoms. If the heterocyclic radical or the heterocyclic ring is optionally substituted, it can be fused with other carbocyclic or heterocyclic rings. In the case of optionally substituted heterocyclic, the invention also encompasses polycyclic systems, such as, for example, 8-azabicyclo [3.2.1] octanyl or 1-azabicyclo [2.2.1] heptyl. In the case of optionally substituted heterocyclic, the invention also encompasses spirocyclic systems, such as, for example, 1-oxa-5-azaspiro [2.3] hexyl. The heterocyclyl groups according to the invention are, for example, piperidinyl, piperazinyl, morpholinyl, thiomorpholinyl, dihydropyranyl, tetrahydropyranyl, dioxanyl, pyrrolinyl, pyrrolidinyl, imidazolinyl, imidazolidinyl, thiazolidinyl, oxazolidinyl, dioxazolidinyl, dioxazolidinyl, dioxanolidine -hydrofuranyl, dihydrofuranyl, oxetanil, oxiranyl, azetidinyl, aziridinyl, oxazetidinyl, oxaziridinol, oxazepanil, oxazinanil, azepanyl, oxopyrrolidinyl, dioxopyrrolidinyl, oxomorpholinyl, oxoporazinil and oxopiperazinil
[057] Heteroarylene, that is, heteroaromatic systems, has a particular significance. According to the invention, the term heteroaryl represents heteroaromatic compounds, that is, completely unsaturated aromatic heterocyclic compounds, which are in the above definition of heterocycles. Preference is given to 5 to 7 membered rings having 1 to 3, preferably 1 or 2 identical or different heteroatoms from the above group. Heteroaryl groups according to the invention are, for example, furyl, thienyl, pyrazolyl, imidazolyl, 1,2,3- and 1,2,4-triazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-, 1, 3,4-, 1,2,4- and 1,2,5-oxadiazolyl, azepinyl, pyrrolyl, pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, 1,3,5-, 1,2,4- and 1,2, 3-triazinyl, 1,2,4-, 1,3,2-, 1,3,6- and 1,2,6- oxazinyl, oxepinil, tiepinil, 1,2,4-triazolonil and 1,2,4 - diazepinil. The heteroaryl groups according to the invention can also be replaced by one or more identical or different radicals.
[058] Substituted groups, such as alkyl, alkenyl, alkynyl, cycloalkyl, aryl, phenyl, benzyl, heterocyclyl and substituted heteroaryl radicals are, for example, a substituted radical derived from the unsubstituted base structure, where the substituents are, for example, one or more, preferably 1, 2 or 3, radicals from the group of halogen, alkoxy, alkylsulfanyl, hydroxyl, amino, nitro, carboxyl or a group equivalent to the group carboxyl, cyano, isocyan, azido, alkoxycarbonyl , alkylcarbonyl, formyl, carbamoyl, mono- and N, N-dialkylaminocarbonyl, substituted amino, such as acylamino, mono- and N, N-dialkylamino, trialkylsilyl and optionally substituted aryl, optionally substituted aryl, optionally substituted heterocyclyl, where each of the latter cyclic groups can also be linked via heteroatoms or divalent functional groups, such as in the alkyl radicals mentioned, and alkylsulfinyl, including both the enantiomers of the alkyl group lsulfonyl, alkylsulfonyl, alkylphosphinyl, alkylphosphonyl, and in the case of cyclic radicals (= "cyclic backbone"), also alkyl, haloalkyl, alkylsulfanylalkyl, alkoxyalkyl, optionally substituted mono- and N, N-dialkylaminoalkyl and hydroxy.
[059] The term "substituted" groups, such as substituted alkyl, etc., includes, as substituents, in addition to the saturated hydrocarbon radicals mentioned, corresponding to unsaturated aliphatic and aromatic radicals, such as optionally substituted alkenyl, alkynyl, alkenyloxy, alkynyloxy, alkenylthio, alkynylthio, alkenyloxycarbonyl, alkynyloxycarbonyl, alkenylcarbonyl, alkynylcarbonyl, mono- and N, N-dialkylenylaminocarbonyl, mono- and dialquinylaminocarbonyl, mono- and N, N-dialkylenylamino, mono- and N, N-dialquinylyl-alkylquinyl, trialyl substituted, optionally substituted cycloalkynyl, phenyl, phenoxy, etc. In the case of cyclic radicals substituted with aliphatic components in the ring, also include cyclic systems with such substituents attached to the ring by a double bond, for example, those having an alkylidene group, such as methylidene or ethylidene, or an oxo group, an imino and substituted imino group.
[060] When two or more radicals form one or more rings, they can be carbocyclic, heterocyclic, saturated, partially saturated, unsaturated, for example, also aromatic and additionally substituted.
[061] The substituents mentioned by way of example ("first substituent level") may, if they contain hydrocarbon-containing moieties, optionally be further substituted therein ("second substituent level"), for example, by one of the substituents, as defined for the first substituting level. The still corresponding substituting levels are possible. The term "substituted radical" preferably covers only one or two substituent levels.
[062] Preferred substituents for the levels of substituents are, for example, amino, hydroxy, halogen, nitro, cyano, isocyan, mercapto, isothiocyanate, carboxyl, carboxamide, SF5, aminosulfonyl, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, N- monoalkylamino, N, N-dialkylamino, N-alkanoylamino, alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, cycloalkenyloxy, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, aryloxycarbonyl, alkyl, alkylenyl, alkylenyl, alkylenyl, alkylenyl, alkylenyl alkylsulfinyl and alkylsulfenyl, in which both enantiomers of the alkylsulfinyl group are included, alkylsulfonyl, N-monoalkylaminosulfonyl, N, N-dialkylaminosulfonyl, alauylphosphinyl, alkylphosphonyl, where in the case of alkylphosphinyl and alkylsulfonyl, both are alkylphenylsulfonyl N-dialkylaminocarbonyl, N-alkanoylaminocarbonyl, N-alkanoyl- N-alkylaminocarbonyl , aryl, aryloxy, benzyl, benzyloxy, benzylthio, arylthio, arylamino, benzylamino, heterocyclyl and trialkylsilyl.
[063] The substituents comprising a plurality of substituents levels are preferably alkoxyalkyl, alquilsulfanilalquil, alquilsulfanilalcóxi, alkoxyalkoxy, phenethyl, benzyloxy, haloalkyl, halocycloalkyl, haloalkoxy, haloalquilsulfanil, haloalkylsulfinyl, haloalkylsulfonyl, haloalcanoil, haloalkylcarbonyl, haloalcoxicarbonil, haloalcoxialcóxi, haloalcoxialquilsulfanil , haloalkoxyalkyl, haloalkoxyalkyl.
[064] In the case of radicals having carbon atoms, preference is given to those having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, especially 1 or 2 carbon atoms. Preference is generally given to substituents from the halogen group, for example, fluorine and chlorine, (C1-C4) alkyl, preferably methyl or ethyl, halo (C1-C4) alkyl, preferably trifluoromethyl, alkoxy (C1-C4), preferably methoxy or ethoxy, haloalkoxy (C1-C4), nitro and cyano. Particular preference is given here for the methyl, methoxy, fluorine and chlorine substituents.
[065] Substituted amino, such as mono- or disubstituted amino means a radical of the group from the substituted amino radicals, which are N-substituted, for example, by one or two identical or different radicals of the group consisting of alkyl, hydroxy , amino, alkoxy, acyl and aryl; preferably, N-monoalkylamino and N, N-dialkylamino, (for example, methylamino, ethylamino, N, N-dimethylamino, N, N-diethylamino, N, N-di-n-propylamino, N, N-di groups -isopropylamino or N, N-dibutylamino), N-monoalkoxyalkylamino or N, N-dialcoxyalkylamino (e.g., N-methoxymethylamino, N-methoxyethylamino, N, N-di (methoxymethyl) amino or N, N-di (methoxyethyl) amino ), N-monoarylamino and N, N-diarylamino, such as optionally substituted anilines, acylamino, N, N-diacylamino, N-alkyl-N-arylamino, N-alkyl-N-acylamino and also N-saturated heterocycles; preference is given here for alkyl radicals having 1 to 4 carbon atoms; here, aryl is preferably phenyl or substituted phenyl; for acyl, the definition given below applies, preferably, alkanoyl (C1-C4). The same applies to hydroxylamino or substituted hydrazino.
[066] According to the invention, the term "cyclic amino groups" encompasses heteroaromatic or aliphatic ring systems having one or more nitrogen atoms. The heterocycles are saturated or unsaturated, consist of one or more fused ring systems and optionally contain additional hetero atoms, such as, for example, one or two nitrogen, oxygen and / or sulfur atoms. In addition, the term also includes groups having a spiro ring or a bridged ring system. The number of atoms that make up the cyclic amino group is not limited and, in the case of a one ring system, for example, it can consist of 3 to 8 ring atoms, and in the case of a 7 to 11 two ring system atoms.
[067] Examples of cyclic amino groups having saturated and unsaturated monocyclic groups having a nitrogen atom as heteroatoms, which may be mentioned are 1-azetidinyl, pyrrolidine, 2-pyrrolidin-1-yl, 1-pyrrolyl, piperidine, 1, 4-dihydropyrazin-1-yl, 1,2,5,6-tetrahydropyrazin-1-yl, 1,4-dihydropyridin-1-yl, 1,2,5,6-tetrahydropyridin- 1-yl, homopiperidinyl; examples of cyclic amino groups having saturated and unsaturated monocyclic groups having two or more nitrogen atoms as heteroatoms, which may be mentioned are 1-imidazolidinyl, 1-imidazolyl, 1-pyrazolyl, 1-triazolyl, 1-tetrazolyl, 1-piperazinyl, 1-homopiperazinyl, 1,2-dihydropiperazin-1-yl, 1,2-dihydropyrimidin-1-yl, perhydropyrimidin-1-yl, 1,4-diazacycloheptan-1-yl; examples of cyclic amino groups having saturated and unsaturated monocyclic groups having one or two oxygen atoms and one to three nitrogen atoms as hetero atoms, such as, for example, oxazolidin-3-yl, 2,3-dihydroisoxazole-2- il, isoxazol-2-yl, 1,2,3-oxadiazin-2-yl, morpholino, examples of cyclic amino groups having saturated and unsaturated monocyclic groups having from one to three nitrogen atoms and one to two sulfur atoms as heteroatoms , which may be mentioned are thiazolidin-3-yl, isothiazolin-2-yl, thiomorpholino, or dioxothiomorpholino; examples of cyclic amino groups having saturated and unsaturated fused cyclic groups that can be mentioned are indol-1-yl, 1,2-dihydrobenzimidazol-1-yl, perhydropyrrol [1,2-a] pyrazin-2-yl; examples of cyclic amino groups having spirocyclic groups that can be mentioned are 2-azaspiro [4,5] decan-2-yl; examples of cyclic amino groups having heterocyclic bridging groups that can be mentioned are 2-azabicyclo [2.2.1] heptan-7-yl.
[068] Substituted amino also includes quaternary ammonium compounds (salts) with four organic substituents on the nitrogen atom.
[069] Optionally substituted phenyl is preferably phenyl which is unsubstituted or mono- or polysubstituted, preferably until tri-substituted, by identical or different radicals from the halogen group, alkyl (C1-C4), alkoxy (C1 -C4), (C1-C4) -alkoxy- (C1-C4) -alkoxy, (C1-C4) -alkoxy- (C1-C4) -alkyl, (C1-C4) - haloalkyl, (C1-C4) - haloalkoxy, alkylsulfanyl (C1-C4), haloalkylsulfanyl (C1-C4), cyano, isocyan and nitro, for example, o-, m- and p-tolyl, dimethylphenyl, 2-, 3- and 4-chlorophenyl, 2-, 3- and 4-fluorophenyl, 2-, 3- and 4-trifluoromethyl- and -trichloromethylphenyl, 2,4-, 3,5-, 2,5- and 2,3-dichlorophenyl, o-, m- and p- methoxyphenyl.
[070] Optionally substituted cycloalkyl is preferably cycloalkyl, which is unsubstituted or mono- or polysubstituted, preferably even trisubstituted, by identical or different radicals from the group of halogen, cyano, (C1-C4) alkyl, (C1-C4) alkoxy, (C1-C4) - (C1-C4) -alkoxy, (C1-C4) -alkoxy- (C1-C4) -alkyl, haloalkyl (C1-C4) and haloalkoxy (C1-) C4), especially by one or two (C1-C4) -alkyl radicals.
[071] Optionally substituted heterocyclyl is preferably heterocyclyl, which is unsubstituted or mono- or polysubstituted, preferably even trisubstituted, by identical or different radicals from the group of halogen, cyano, (C1-C4) alkyl, (C1-C4) alkoxy, (C1-C4) - (C1-C4) -alkoxy, (C1-C4) -alkoxy- (C1-C4) -alkyl, haloalkyl (C1-C4), haloalkoxy (C1-) C4), nitro and oxo, especially mono- or polysubstituted by radicals of the group of halogen, alkyl (C1-C4), alkoxy (C1-C4), haloalkyl (C1-C4) and oxo, more preferably, substituted by one or two (C1-C4) alkyl radicals.
[072] Examples of alkyl-substituted heteroaryl groups are furylmethyl, thienylmethyl, pyrazolylmethyl, imidazolylmethyl, 1,2,3- and 1,2,4-triazolylmethyl, isoxazolylmethyl, thiazolylmethyl, isothiazolylmethyl, 1,2,3-, 1,3 , 4-, 1,2,4- and 1,2,5-oxadiazolylmethyl, azepinylmethyl, pyrrolylmethyl, pyridylmethyl, pyridazinylmethyl, pyrimidinylmethyl, pyrazinylmethyl, 1,3,5-, 1,2,4- and 1,2,3 - triazinylmethyl, 1,2,4-, 1,3,2-, 1,3,6- and 1,2,6- oxazinylmethyl, oxepinylmethyl, tiepinylmethyl and 1,2,4-diazepinylmethyl.
[073] Salts which are suitable according to the invention of the compounds according to the invention, for example, salts with bases or acid addition salts, are all the usual non-toxic salts, preferably their agriculturally and / or salts or physiologically acceptable. For example, salts with bases or acid addition salts. Preference is given to salts with inorganic bases such as, for example, alkali metal salts (for example, sodium, potassium or cesium salts), alkaline earth metal salts (for example, calcium or magnesium salts), salts of ammonium or salts with organic bases, in particular with organic amines, such as, for example, triethylammonium, dicyclohexylammonium, N, N'-dibenzylethylenediamonium, pyridinium, picolinium or ethanolammonium salts, salts with inorganic acids (eg hydrochlorides, hydrobromides, dihydrosulfates, trihydrosulfates or phosphates), salts with organic carboxylic acids or organic sulphoacids (for example, formats, acetates, trifluoroacetates, maleates, tartrates, methanesulfonates, benzenesulfonates or 4-toluenesulfonates). It is known that t-amines, such as some of the compounds according to the invention, are capable of forming N-oxides, which also represent salts according to the invention.
[074] The compounds according to the invention may, depending on the nature of the substituents, be in the form of geometric isomers and / or optically active isomers or mixtures of corresponding isomers in different compositions. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers. Accordingly, the invention encompasses both pure stereoisomers as well as any mixture of these isomers.
[075] If appropriate, the compounds according to the invention can be present in various polymorphic forms or as a mixture of different polymorphic forms. Both pure polymorphs and mixtures of polymorphs are provided by the present invention and can be used according to the invention.
[076] The compounds of the general formula (I) can be mixed or applied together with other insecticides, nematicides, acaricides or active antimicrobial compounds. In these mixtures or binding applications, synergistic effects occur, that is, the observed effect of this mixture or binding applications is greater than the total effects of individual active compounds in these applications. Examples of such a mixture or combination partners are: (1) acetylcholinesterase (AChE) inhibitors, such as, for example, carbamates, for example, alanicarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxy, carbaryl, carbofuran, carbosulfan, etiofencarb , fenobucarb, formetanato, furatiocarb, isoprocarb, metiocarb, metomil, metolcarb, oxamil, pirimicarb, propoxur, thiodicarb, thiophanan, triazamate, trimetacarb, XMC and xylilcarb; or organophosphates, for example, acephate, azametiphos, azymphos-ethyl, azymphos-methyl, cadusaphos, chlorethoxyphos, chlorfenvinfos, chlorephs, chlorpyrifos, chlorpyrifos-methyl, coumafos, cyanophos, demeton-S-methyl, diazinon, dichlorides, dichlorides dimetoate, dimethylvinfos, disulfoton, EPN, etion, etoprofos, famfur, fenamiphos, fenitrothion, fention, fostiazate, heptenophos, imiciafos, isofenfos, isopropyl O- (methoxyminothiofosforil) salicylate, methoxy, methoxy, moxation, maoxation, maoxation, nalede, ometoate, oxidemeton-methyl, parathion, parathion-methyl, fentoate, phorate, fosalone, fosmete, phosphamidia, foxima, pirimiphos-methyl, profenofos, propetanfos, protiofos, piraclofos, piridafention, quinalfos, sulfotepe, terfos, tempeos, tempe tetrachlorvinfos, thiomethane, triazophos, trichlorfom and vamidothion; (2) GABA-dependent chloride channel antagonists, such as, for example, cyclodienes organochlorines, for example, chlordane and endosulfan; or phenylpyrazoles (fiprol), for example, ethiprole and fipronil; (3) voltage-dependent sodium channel blockers / sodium channel modulators, such as, for example, pyrethroids, for example, acrinatrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, isomer bioalethrin s-cyclopentenyl, bioresmethrin, cycloprotrine, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, tetamethyrrine, zeta-cypermethrin (1) transisomers], deltamethrin, empentrin [(EZ) - (1R) -isomers], sphenvalerate, etofenprox, fenpropatrin, fenvalerate, flucitrinate, flumethrin, tau-fluvalinate, halfenprox, imiprotrin, cadetrin, permethrin, permethrin (1) transisomer], pralethrin, pyrethrins (pyrethrin), resmethrin, silafluofen, teflutrin, tetramethrin, tetramethrin [(1R) - isomers)], tralometrine and transflutrin; or DDT; or methoxychlorine; (4) nicotinergic acetylcholine receptor (nAChR) agonists, such as, for example, neonicotinoids, for example, acetamipride, clothianidin, dinotefuran, imidacloprid, nitenpiram, thiaclopride and thiamethoxam; or nicotine; or sulfoxaflor. (5) allosteric activators of the nicotinergic acetylcholine (nAChR) receptor such as, for example, spinosyn, for example, spinors and spinosad; (6) chloride channel activators, such as, for example, avermectins / milbemycins, for example, abamectin, emamectin benzoate, lepimectin and milbemectin; (7) juvenile hormone mimics such as, for example, juvenile hormone analogs, for example, hydroprene, quinoprene and methoprene; or phenoxycarb; or pyriproxifene; (8) active compounds with unknown or non-specific mechanisms of action, such as, for example, alkyl halides, for example, methyl bromide and other alkyl halides; or chloropicrin; or sulfuryl fluorine; or borax; or emetic tartar; (9) selective appetite suppressant, for example, pymetrozine; or flonicamide; (10) moderate growth inhibitors, for example, clofentezine, hexitiazox and diflovidazin; or ethoxazole; (11) microbial switches of the insect intestine membrane, for example, Bacillus thuringiensis subspecies israelensis, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis and vegetable proteins Bt: Cry1A, Cry1Ab1, Cry1Ab1, Cry1Ab1 , Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / 35Ab1; or Bacillus sphaericus; (12) oxidative phosphorylation inhibitors, ATP disruptors, for example, diafentiuron; or organostannic compounds, for example, azocyclotin, cyhexin and fenbutatin oxide; or propargite; or tetradifon; (13) oxidative phosphorylation decouplers acting by interrupting the H proton gradient, such as, for example, chlorfenapyr, DNOC and sulfluramide; (14) nicotinergic acetylcholine receptor antagonists, such as, for example, bensultape, cartape hydrochloride, thiocyclam, sodium thiosultape; (15) Chitin biosynthesis inhibitors, type 0, such as, for example, bistrifluron, chlorfluazuron, diflubenzuron, flucicloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron; (16) chitin biosynthesis inhibitors, type 1, such as, for example, buprofezin; (17) dipter switch switches, such as, for example, cyromazine; (18) ecdysone receptor agonists, such as, for example, chromafenozide, halofenozide, methoxyfenozide and tebufenozide; (19) octopaminergic agonists, such as, for example, amitraz; (20) Complex-III electron transport inhibitors, such as, for example, hydramethylnone or acequinocil or fluacripyrim. (21) Complex-I electron transport inhibitors, for example, METI acaricides, for example, phenazaquin, fenpyroximate, pyrimidifene, pyridabene, tebufenpirade and tolfenpirade; or rotenone (Derris); (22) tension-dependent sodium channel blockers, for example, indoxacarb or metaflumizone; (23) acetyl-CoA carboxylase inhibitors, such as, for example, derivatives of tetronic and tetramic acids, for example, spirodiclofen, spiromesifene and spirotetramate; (24) complex IV electron transport inhibitors, such as, for example, phosphines, for example, aluminum phosphide, calcium phosphide, phosphine and zinc phosphide; or cyanide; (25) the electron transport inhibitors of the II-complex, such as, for example, cyienoporafene and cyflumetophen; (28) the effectors of the ryanodine receptor such as, for example, diamides, for example, chlorantraniliprol, cyantraniliprol and flubendiamide.
[077] Other active compounds having an unknown mechanism of action, such as, for example, amidoflumet, azadiractin, benclothiaz, benzoxide, biphenazate, bromopropylate, quinomethionate, cryolite, dicofol, diflovidazine, fluensulfone, flufenin, flufiprol, fluofluid, fluofluid, fluopyrid, fluofluid, fluufid , iprodione, meperflutrin, pyridalyl, pyrifluquinazon, tetramethylflutrin and iodomethane; and, in addition, preparations based on Bacillus firmus (particularly strain CNCM I-1582, for example, VOTiVO ™, BioNem), and the following known active compounds: 3-bromo-N- {2-bromo-4-chlor-6 - [(1-cyclopropylethyl) carbamoyl] phenyl} -1- (3-chloropyridin-2-yl) - 1H-pyrazol-5-carboxamide (known from WO 2005/077934), 4- {[(6-bromopyrid-3 -yl) methyl] (2-fluoroethyl) amino} furan-2 (5H) - one (known from WO 2007/115644), 4- {[(6-fluoropyrid-3-yl) methyl] (2,2-difluoroethyl ) amino} furan-2 (5H) -one (known from WO 2007/115644), 4- {[(2-chloro-1,3-thiazol-5-yl) methyl] (2-fluoroethyl) amino} furan- 2 (5H) -one (known from WO 2007/115644), 4- {[(6-chloropyrid-3-yl) methyl] (2-fluoroethyl) amino} furan-2 (5H) -one (known from WO 2007 / 115644), flupiradifurone, 4- {[(6-chloro-5-fluoropyrid-3-yl) methyl] (methyl) amino} furan-2 (5H) -one (known from WO 2007/115643), 4- { [(5,6-dichloropyrid-3-yl) methyl] (2-fluoroethyl) amino} furan-2 (5H) -one (known from WO 2007/115646), 4- {[(6-chloro-5-fluoropyrid -3- il) methyl] (cyclopropyl) amino} fu ran-2 (5H) -one (known from WO 2007/115643), 4- {[(6-chloropyrid-3-yl) methyl] (cyclopropyl) amino} furan-2 (5H) -one (known from EP A 0 539 588), 4- {[(6-chloropyrid-3-yl) methyl] (methyl) amino} furan-2 (5H) -one (known from EP A 0 539 588), {[1- (6- chloropyridin-3-yl) ethyl] (methyl) oxido-X4-sulfanilidene} cyanamide (known from WO2007 / 149134) and its diastereomers {[(1R) -1- (6-chloropyridin-3-yl) ethyl] (methyl ) oxido-X4-sulfanilidene} cyanamide (A) and {[(1S) -1- (6-chloropyridin-3-yl) ethyl] (methyl) oxido-X4-sulfanilidene} cyanamide (B) (similar known from WO 2007 / 149134) and also diastereomers [(R) - methyl (oxido) {(1R) -1- [6- (trifluoromethyl) pyridin-3-yl] ethyl} - X4-sulfanilidene] cyanamide (A1) and [(S) -methyl (oxido) {(1S) -1- [6- (trifluoromethyl) pyridin-3-yl] ethyl} -X4-sulfanilidene] cyanamide (A2), identified as group A diastereomer (known from WO 2010/074747, WO 2010/074751), [(R) -methyl (oxide) {(1S) -1- [6- (trifluoromethyl) pyridin-3-yl] ethyl} -X4-sulfanilidene] cyanamide (B1) and [(S) -methyl (oxide) {(1R) -1- [ 6- (trifluoromethyl) pyridin-3-yl] ethyl} -X4-sulfanilidene] cyanamide (B2), identified as group B diastereomer (also known from WO 2010/074747, WO 2010/074751) and 11- (4-chlorine -2,6- dimethylphenyl) -12-hydroxy-1,4-dioxa-9-azadiespiro [4.2.4.2] tetradec-11-en-10-one (known from WO 2006/089633), 3- (4'- fluoro-2,4-dimethylbiphenyl-3-yl) -4-hydroxy-8-oxa-1-aza-spiro [4.5] dec-3-en-2-one (known from WO 2008/067911), 1- { 2-fluoro-4-methyl-5- [(2,2,2-trifluoroethyl) sulfinyl] phenyl} -3- (trifluoromethyl) -1H-1,2,4-triazole-5-amine (known from WO 2006 / 043635), aphidopyropene (known from WO 2008/066153), 2-cyano-3- (difluoromethoxy) -N, N-dimethylbenzolsulfonamide (known from WO 2006/056433), 2-cyano-3- (difluoromethoxy) -N -methylbenzolsulfonamide (known from WO 2006/100288), 2-cyano-3- (difluoromethoxy) -N-ethylbenzenesulfonamide (known from WO 2005/035486), 4- (difluoromethoxy) -N-ethyl-N-methyl-1,2 -benzothiazole-3-amine- 1,1-dioxide (known from WO 2007/057407), N- [1- (2,3- dime tilphenyl) -2- (3,5-dimethylphenyl) ethyl] -4,5-dihydro-1,3-thiazol-2-amine (known from WO 2008/104503), {1'- [(2E) - 3- (4-chlorophenyl) prop-2-en-1-yl] -5-fluorospiro [indol-3,4'-piperidine] -1 (2H) -yl} (2-chloropyridin-4-yl) methanone ( known from WO 2003/106457), 3- (2,5-dimethylphenyl) -4-hydroxy-8-methoxy-1,8-diaza-spiro [4.5] dec-3-en-2-one (known from WO 2009 / 049851), 3- (2,5-dimethylphenyl) -8-methoxy-2-oxo-1,8-diaza-spiro [4.5] dec-3-en-4-yl ethyl carbonate (known from WO 2009 / 049851), 4- (but-2-in-1-yloxy) -6- (3,5-dimethylpiperidin-1-yl) -5-fluoropyrimidine (known from WO 2004/099160), (2,2,3, 3,4,4,5,5- octafluoropentyl) (3,3,3-trifluoropropyl) malononitrile (known from WO 2005/063094), (2,2,3,3,4,4,5,5- octafluoropentyl) (3,3,4,4,4-pentafluorobutyl) malononitrile (known from WO 2005/063094), 8- [2- (cyclopropylmethoxy) -4- (trifluoromethyl) phenoxy] -3- [6- (trifluoromethyl) pyridazin- 3-yl] -3-azabicyclo [3.2.1] octane (known from WO 2007/040280), flometoquine, PF1364 (CAS Reg. No. 1204776- 60-2) (c known from JP 2010/018586), 5- [5- (3,5-dichlorophenyl) -5- (trifluoromethyl) -4,5-dihydro-1,2-oxazol-3-yl] -2- (1H-1,2,4-triazol-1-yl) benzonitrile (known from WO 2007/075459), 5- [5- (2-chloropyridin-4-yl) -5- (trifluoromethyl) -4,5- dihydro-1,2-oxazol-3-yl] -2- (1H-1,2,4-triazol-1-yl) benzonitrile (known from WO 2007/075459), 4- [5- (3, 5-dichlorophenyl) -5- (trifluoromethyl) -4,5-dihydro-1,2-oxazol-3-yl] -2-methyl-N- {2-oxo-2- [(2,2,2 - trifluoroethyl) amino] ethyl} benzamide (known from WO 2005/085216), 4- {[(6-chloropyridin-3-yl) methyl] (cyclopropyl) amino} -1,3-oxazol-2 (5H) -one , 4- {[(6-chloropyridin-3-yl) methyl] (2,2-difluoroethyl) amino} -1,3-oxazol-2 (5H) -one, 4- {[(6-chloropyridin-3- yl) methyl] (ethyl) amino} -1,3-oxazol-2 (5H) -one, 4- {[(6-chloropyridin-3-yl) methyl] (methyl) amino} -1,3-oxazole- 2 (5H) -one (all known from WO 2010/005692), piflubumide (known from WO 2002/096882), 2- [2 - ({[3-bromo- 1- (3-chloropyridin-2-yl) - 1H-pyrazol-5-yl] carbonyl} amino) -5-chloro-3-methylbenzoyl] -2-methylhydrazinecarboxylate methyl (known from WO 2005/085216), 2- [2 - ({[3-bromo-1- (3-chloropyridin-2-yl) -1H-pyrazol-5-yl] carbonyl} amino) -5- methyl cyano-3-methylbenzoyl] -2-ethylhydrazinecarboxylate (known from WO 2005/085216), 2- [2 - ({[3-bromo-1- (3-chloropyridin-2-yl) -1H-pyrazole -5-yl] carbonyl} amino) -5-cyano- 3-methylbenzoyl] -2-methyl-hydrazinecarboxylate (known from WO 2005/085216), 2- [3,5-dibromo-2 - ({[3 methyl-bromo- 1- (3-chloropyridin-2-yl) -1H-pyrazol-5-yl] carbonyl} amino) benzoyl] -1,2-diethylhydrazinecarboxylate (known from WO 2005/085216), 2- [3,5-dibromo-2- ({[3-bromo-1- (3-chloropyridin-2-yl) -1H-pyrazol-5-yl] carbonyl} amino) benzoyl] -2-ethyl-hydrazinecarboxylate (known from WO 2005/085216), (5RS, 7RS; 5RS, 7SR) -1- (6-chloro-3-pyridylmethyl) -1,2,3,5,6,7-hexahydro-7-methyl-8 - nitro-5-propoxy-imidazo [1,2-a] pyridine (known from WO 2007/101369), 2- {6- [2- (5-fluoropyridin-3-yl) -1,3-thiazol-5 - yl] pyridin-2-yl} pyrimidine (known from WO 2010/006713), 2- {6- [2- (pyridin-3-yl) -1,3-thiazol-5 -yl] pyridin-2-yl} pyrimidine (known from WO 2010/006713), 1- (3-chloropyridin-2-yl) -N- [4-cyano-2-methyl-6- (methylcarbamoyl) phenyl] - 3- {[5- (trifluoromethyl) -1H-tetrazol-1-yl] methyl} -1H-pyrazol-5-carboxamide (known from WO 2010/069502), 1- (3-chloropyridin-2-yl) -N - [4-cyano-2-methyl-6- (methylcarbamoyl) phenyl] -3- {[5- (trifluoromethyl) -2H-tetrazol-2-yl] methyl} -1H-pyrazol-5-carboxamide (known from WO 2010/069502), N- [2- (tert-butylcarbamoyl) -4-cyano-6-methylphenyl] -1- (3-chloropyridin-2-yl) -3- {[5- (trifluoromethyl) - 1H-tetrazole -1-yl] methyl} -1H-pyrazol-5-carboxamide (known from WO 2010/069502), N- [2- (tert-butylcarbamoyl) -4-cyano-6-methylphenyl] -1- (3-chloropyridin -2-yl) -3- {[5- (trifluoromethyl) - 2H-tetrazol-2-yl] methyl} -1H-pyrazol-5-carboxamide (known from WO 2010/069502), (1E) -N- [ (6-chloropyridin-3-yl) methyl] -N'- cyano-N- (2,2-difluoroethyl) etanimide-amide (known from WO 2008/009360), N- [2- (5-amino-1, 3,4-thiadiazol-2-yl) -4-chloro-6-methylphenyl] -3-bromo-1- (3-chloropyridin-2-yl) -1H-pyrazol-5-carboxami da (known from CN 102057925), 2- [3,5-dibromo-2- ({[3-bromo-1- (3-chloropyridin-2-yl) -1H-pyrazol-5-yl] carbonyl} amino) benzoyl] -2-ethyl-1-methylhydrazinecarboxylate (known from WO 2011/049233), heptaflutrin, pyriminostrobin, fluphenoxostrobin and 3-chloro-N2- (2-cyanopropan-2-yl) -N1- [4- (1,1,1,2,3,3,3-heptafluoropropan-2-yl) -2-methylphenyl] phthalamide (known from WO2012 / 034472).
[078] Antimicrobial active compounds: (1) ergosterol biosynthesis inhibitors, for example, aldimorph, azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazol, diphenoconazole, diniconazole, diniconazole-M, dodemoricon, acetate, dodemorazole, acetate, dodemorazole, acetate, and fenarimol, fenbuconazole, fenhexamide, fenpropidine, fenpropimorph, fluquinconazole, flurprimidol, flusilazole, flutriafol, furconazole, furconazol-cis, hexaconazole, imazalil, imazalil sulfate, imibenconazol, oxobolazole, methazolazole, ipconazole, ipconazole penconazole, piperalin, prochloraz, propiconazole, protioconazole, pyributicarb, pirifenox, quinconazole, simeconazole, spiroxamine, tebuconazole, terbinafine, tetraconazole, triadimefon, triadimenol, tridemorfe, triflumizol, pyridazole, triconazole, triconazole, triforazol, triforazole (4-chlorophenyl) -2- (1H-1,2,4-triazol-1-yl) cycloheptanol, 1- (2,2-dimethyl-2,3-dihydro-1H-inden-1-yl) -1H-imide methyl zol-5-carboxylate, N '- {5- (difluoromethyl) -2-methyl-4- [3- (trimethylsilyl) propoxy] phenyl} -N-ethyl-N-methylimidoformamide, N-ethyl-N-methyl -N '- {2-methyl-5- (trifluoromethyl) -4- [3- (trimethylsilyl) propoxy] phenyl} imidoformamide and O- [1- (4-methoxyphenoxy) -3,3-dimethylbutan-2-yl] 1H-imidazole-1-carbothioate; (2) respiration inhibitors (respiratory chain inhibitors), for example, bixafen, boscalide, carboxine, diflumetorim, fenfuram, fluopyram, flutolanil, fluxpyroxade, furametpir, furmeciclox, isopyrazam, mixture of 1RS, 4SR sin-epimeric racemate 9RS and mixture of the anti-epimeric racemate 1RS, 4SR, 9SR, isopirazam (anti-epimeric racemate), isopyrazam (anti-epimeric enantiomer 1R, 4S, 9S), isopyrazam (anti-epimeric enantiomer 1S, 4R, 9R), isopirazam ( syn-epimeric racemate 1RS, 4SR, 9RS), isopirazam (anti-epimeric enantiomer 1R, 4S, 9R), isopirazam (syn-epimeric enantiomer 1S, 4R, 9S), mepronil, oxycarboxine, penflufen, pentiopirade, silkxane, tifl -methyl-N- [2- (1,1,2,2-tetrafluoroethoxy) phenyl] - 3- (trifluoromethyl) -1H-pyrazol-4-carboxamide, 3- (difluoromethyl) -1-methyl-N- [2 - (1,1,2,2- tetrafluoroethoxy) phenyl] -1H-pyrazol-4-carboxamide, 3- (difluoromethyl) -N- [4-fluoro-2- (1,1,2,3,3,3 - hexafluoropropoxy) phenyl] -1-methyl-1H-pyrazol-4-carboxamide and N- [1- (2,4-dichloropheni l) -1-methoxypropan-2-yl] -3- (difluoromethyl) -1-methyl-1H-pyrazol-4-carboxamide; (3) respiration inhibitors (respiratory chain inhibitors) acting on the respiratory chain complex III, for example, ametoctradin, amisulbrom, azoxystrobin, cyazofamide, dimoxystrobin, enestroburin, famoxadone, phenamidone, fluoxastrobin, cresoxime-methyl, metominostrobin, or metominostrobin, or picoxystrobin, pyraclostrobin, pyramethostrobin, piraoxystrobin, pyribencarb, trifloxystrobin, (2E) -2- (2- {[6- (3-chloro-2-methylphenoxy) -5-fluoropyrimidin-4-yl] oxy} phenyl) -2- (methoxyimino) -N-methylethylamide, (2E) -2- (methoxyimino) -N-methyl-2- (2- {[({(1E) -1- [3- (trifluoromethyl) phenyl] ethylidene } amino) oxy] methyl} phenyl) wet ethane, (2E) -2- (methoxyimino) -N-methyl-2- {2- [(E) - ({1- [3- (trifluoromethyl) phenyl] ethoxy} imino) methyl] phenyl} ethanamide, (2E) -2- {2- [({[(1E) -1- (3- {[(E) -1-fluoro-2-phenylethyl] oxy} phenyl) ethylidene] amino} oxy) methyl] phenyl} -2- (methoxyimino) -N-methylethylamide, (2E) -2- {2- [({[(2E, 3E) -4- (2,6-dichlorophenyl ) but-3-en-2-ylidene] amino} oxy) methyl] phenyl} -2- (methoxyimino) -N- methylethylamide, 2-chloro-N- (1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl) pyridine-3-carboxamide, 5-methoxy-2-methyl-4- (2- {[({(1E) -1- [3- (trifluoromethyl) phenyl] ethylidene} amino) oxy] methyl} phenyl) -2,4-dihydro-3H-1,2,4-triazole-3-one , Methyl (2E) -2- {2- [({cyclopropyl [(4-methoxyphenyl) imino] methyl} sulfanyl) methyl] phenyl} -3-methoxyprop-2-enoate, N- (3-ethyl-3, 5,5-trimethylcyclohexyl) -3- (formylamino) -2-hydroxybenzamide, 2- {2- [(2,5-dimethylphenoxy) methyl] phenyl} -2-methoxy-N-methylacetamide and (2R) -2 - {2- [(2,5-dimethylphenoxy) methyl] phenyl} -2-methoxy-N-methylacetamide; (4) mitosis and cell division inhibitors, for example, benomyl, carbendazim, chlorphenazole, dietofencarb, etaboxam, fluopicolide, fuberidazole, pencicuron, thiabendazole, thiophanate-methyl, thiophanate, zoxamide, 5-chloro-7- (4-methylpiperidine) -1-yl) -6- (2,4,6-trifluorophenyl) [1,2,4] triazole [1,5-a] pyrimidine and 3-chloro-5- (6-chloropyridin-3-yl) - 6-methyl-4- (2,4,6-trifluorophenyl) pyridazine; (5) compounds with activity at multiple sites, for example, Bordeaux mixture, captafol, captan, chlorothalonil, copper formulations such as copper hydroxide, copper naphthenate, copper oxide, copper oxychloride, copper sulfate, diclofluanide, ditianon, dodine, dodine-free base, ferbam, fluorofolpet, folpet, guazatin, guazatin acetate, iminoctadine, iminoctadine albesylate, iminoctadine triacetate, mancobre, mancozebine, manebe, metim, metiram, zinc, zinc propineb, sulfur and sulfur preparations, for example, calcium polysulfide, draw, tolylfluanide, zineb and ziram; (6) resistance inducers, for example, acibenzolar-S-methyl, isothianyl, probenazole and thiadinyl; (7) amino acid and protein biosynthesis inhibitors, for example, andoprim, blasticidin-S, cyprodinil, casugamycin, casugamycin hydrochloride hydrate, mepanipyrim and pyrimethanil; (8) inhibitors of ATP production, for example, phentin acetate, fentin chloride, fentin hydroxide and siltiofam; (9) inhibitors of cell wall synthesis, for example, bentiavalicarb, dimetomorph, flumorfe, iprovalicarb, mandipropamide, polyoxins, polyoxorim, validamycin A and valifenalate; (10) inhibitors of lipid and membrane synthesis, for example, biphenyl, chloroneb, dichloran, edifenfos, etridiazole, iodocarb, iprobenfos, isoprothiolan, propamocarb, propamocarb hydrochloride, protiocarb, pyrazophos, quintozene, technazene; (11) melanin biosynthesis inhibitors, for example, carpropamide, diclocimet, phenoxanil, phthalide, piroquilon and tricyclazole; (12) inhibitors of nucleic acid synthesis, for example, benalaxyl, benalaxyl-M (chiralaxyl), bupirimate, clozilacon, dimethyrimol, ethirimol, furalaxil, himexazole, metalaxyl, metalaxyl-M (mefenoxam), oxurixol, oxadixyl, acid ; (13) signal transduction inhibitors, for example, clozolinate, fenpiclonil, fludioxonil, iprodione, procymidone, quinoxyfen and vinclozoline; (14) uncouplers, for example, binapacril, dinocape, ferimzone, fluazinam and meptildinocape; (15) other compounds, for example, bentiazole, betoxazina, capsimicina, carvona, quinometinato, clazafenone, cufranebe, ciflufenamide, cymoxanil, cyprosulfamide, dazomete, debacarb, dichlorfen, diclomez, difenzoquat, diphenylmethylamine, diphenylamine, diphenylamine , fluoromide, flusulfamide, flutianyl, fosetyl-aluminum, fosetyl-calcium, fosetyl-sodium, hexachlorobenzene, irumamycin, metasulfocarb, methyl isothiocyanate, metrafenon, mildiomycin, natamycin, nickel dimethyldithiocarbamate, nitrotal-isopropyl, oxopropyl, oxopropyl, oxopropyl, oxopropyl, isopropyl, oxo-pentyl, oxo-pentyl, oxo-pentyl, oxo-pentyl, oxo-pentyl, oxo-pentyl, oxo-pentyl, oxo-pentyl, oxo-pentyl, oxo-pentyl, oxo-pentyl, oxo-pentyl, oxo-oxo-oxyl, oxo-oxo. and salts thereof, phenothrin, phosphoric acid and its salts, propamocarb-phosethylate, propanosine-sodium, proquinazide, pyrrolnitrine, tebufloquine, keyboardoftalam, tolnifanide, triazoxide, triclamide, zarylamide, 1- (4- {4- [(5R) -5 - (2,6-difluorophenyl) -4,5-dihydro-1,2-oxazol-3-yl] -1,3-thiazol-2-yl} piperidin-1-yl) -2- [5- methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] ethanone, 1- (4- {4- [(5S) -5- (2,6-difluorophenyl) - 4,5-dihydro-1,2-oxazol-3-yl] -1,3-thiazol-2-yl} piperidin-1-yl) -2- [5-methyl-3- (trifluoromethyl) -1H -pyrazol-1-yl] ethanone, 1- (4- {4- [5- (2,6-difluorophenyl) -4,5-dihydro-1,2-oxazol-3-yl] -1,3 -thiazol-2-yl} piperidin-1-yl) -2- [5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] ethanone, 1- (4-methoxyphenoxy) -3,3-dimethylbutan -2-yl-1H-imidazole-1-carboxylate, 2,3,5,6-tetrachloro-4- (methylsulfonyl) pyridine, 2,3-dibutyl-6-chlorothieno [2,3-d] pyrimidin-4 ( 3H) -one, 2- [5- methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] -1- (4- {4- [(5R) -5-phenyl-4,5-di- hydro-1,2-oxazol-3-yl] -1,3-thiazol-2-yl} piperidin-1-yl) ethanone, 2- [5-methyl-3- (trifluoromethyl) - 1H-pyrazol-1- yl] -1- (4- {4- [(5S) -5-phenyl-4,5-dihydro-1,2-oxazol-3-yl] -1,3-thiazol-2-yl} piperidin -1-yl) ethanone, 2- [5- methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] -1- {4- [4- (5-phenyl- 4,5-dihydro- 1,2-oxazol-3-yl) -1,3-thiazol-2-yl] piperidin-1-yl} ethanone, 2-butoxy-6-iodo-3-propyl-4H-chromen-4-one, 2 - chloro-5- [2-chloro-1- (2,6-difluoro-4-methoxyphenyl) -4-methyl-1H -imidazol-5-yl] pyridine, 2-f enylphenol and its salts, 3,4,5-trichloropyridine-2,6-dicarbonitrile, 3- [5- (4-chlorophenyl) - 2,3-dimethyl-1,2-oxazolidin-3-yl] pyridine, 3- chloro-5- (4-chlorophenyl) -4- (2,6-difluorophenyl) -6-methylpyridazine, 4- (4-chlorophenyl) -5- (2,6-difluorophenyl) -3,6-dimethylpyridazine, 5- amino-1,3,4-thiadiazole-2-thiol, 5-chloro-N'-phenyl-N '- (prop-2-in-1-yl) thiophene-2-sulfonohydrazide, 5-methyl-6-octyl - Ethyl [1,2,4] triazole [1,5-a] pyrimidine-7-amine, (2Z) -3-amino-2-cyano-3-phenylprop-2-enoate, N- (4-chlorobenzyl ) -3- [3-methoxy-4- (prop-2-in-1-yloxy) phenyl] propanamide, N- [(4-chlorophenyl) (cyano) methyl] -3- [-3-methoxy-4- (prop-2-in-1-yloxy) phenyl] propanamide, N- [(5-bromo-3-chloropyridin-2-yl) methyl] -2,4-dichloropyridine-3-carboxamide, N- [1- ( 5-bromo-3-chloropyridin-2-yl) ethyl] -2,4-dichloropyridine-3-carboxamide, N- [1- (5-bromo-3-chloropyridin-2-yl) ethyl] -2-fluoro- 4-iodopyridine-3-carboxamide, N - {(E) - [(cyclopropylmethoxy) imino] [6- (difluoromethoxy) -2,3-difluorophenyl] methyl} -2-phenylacetamide, N - {(Z) - [( cyclopropylmethoxy) imino] [ 6- (difluoromethoxy) -2,3- difluorophenyl] methyl} -2-phenylacetamide, N-methyl-2- (1- {[5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] acetyl} piperidin-4-yl) -N- (1,2,3,4-tetrahydronaphthalen-1-yl) -1,3-thiazol-4-carboxamide, N-methyl-2- (1- {[5- methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] acetyl} piperidin-4-yl) -N- [(1R) -1,2,3,4-tetrahydronaphthalen-1-yl] -1 , 3-thiazol-4-carboxamide, N-methyl-2- (1- {[5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] acetyl} piperidin-4-yl) -N- [ (1S) -1,2,3,4-tetrahydronaphthalen-1-yl] -1,3-thiazol-4-carboxamide, {6- [({[(1- methyl-1H-tetrazol-5-yl ) (phenyl) methylidene] amino} oxy) methyl] pyridin-2-yl} pentyl carbamate, phenazine-1-carboxylic acid, quinoline-8-ol and quinolin-8-ol sulfate (2: 1), (16 ) Other active antimicrobial compounds: (16.1) bentiazole, (16.2) betoxazine, (16.3) capsimycin, (16.4) carvone, (16.5) quinomethinate, (16.6) pyrophenone (clazafenone) , (16.7) cufranebe, (16.8) cyflufenamide, (16.9) cymoxanil, (16.10) cyprosulfamide, (16.11) dazomete, (16.12) debacarb, (1 6.13) dichlorophene, (16.14) diclomezine, (16.15) difenzoquat, (16.16) dipenzoquat methyl sulfate, (16.17) diphenylamine, (16.18) EcoMate, (16.19) phenpyrazamine, (16.20) flumetover, (16.21) fluoroimide, (16.22) flusulfamide, (16.23) flutianyl, (16.24) fosetyl aluminum, (16.25) phosethyl calcium, (16.26) fosetyl sodium , (16,27) hexachlorobenzene, (16,28) irumamycin, (16,29) metasulfocarb, (16,30) methyl isothiocyanate, (16,31) metrafenone, (16,32) mildiomycin, (16,33) natamycin, (16.34) nickel dimethyldithiocarbamate, (16.35) nitrotalisopropyl, (16.37) oxamocarb, (16.38) oxyphentin, (16.39) pentachlorophenol and salts, (16.40) phenothrin, (16.41) phosphoric acid and its salts, (16.42) propamocarb-phosethylate, (16.43) propanosine-sodium, (16.44) pyrimorph, (16.45) (2E) - 3- (4- tert-butylphenyl) -3- (2-chloropyridin-4-yl) -1- (morpholin-4-yl) prop-2-en-1-one, (16.46) (2Z) -3- (4- tert-butylphenyl) -3- (2-chloropyridin-4-yl) -1- (morpholin-4-yl) prop-2-en-1-one, (16.47) pyrrolnitrine, (16.48) tebufloquin, (16.49) keyboardoftalam, (16.50) tolnifanide, (16.51) triazoxide, (16.52) triclamide, (16.53) zarylamide, (16.54) (3S, 6S, 7R, 8R) 2- methylpropanoate -8 -benzyl-3- [({3- [(isobutyryloxy) methoxy] -4-methoxypyridin-2-yl} carbonyl) amino] -6-methyl-4,9-dioxo-1,5-dioxonan-7-yl, (16.55) 1- (4- {4- [(5R) -5- (2,6-difluorophenyl) -4,5-dihydro-1,2-oxazol-3-yl] -1,3 -thiazol-2-yl} piperidin-1-yl) -2- [5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] ethanone, (16.56) 1- (4- {4- [(5S) -5- (2,6-difluorophenyl) -4,5-dihydro-1,2-oxazol-3-yl] -1,3-thiazol-2-yl} piperidin-1-yl) -2- [5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] ethanone, (16.57) 1- (4- {4- [5- (2,6-difluorophenyl) -4, 5-dihydro-1,2-oxazol-3-yl] -1,3-thiazol-2-yl} piperidin-1-yl) -2- [5-methyl-3- (trifluoromethyl) - 1H-pyrazole -1-yl] ethanone, 1- (4-methoxyphenoxy) -3,3-dimethylbutan-2-yl, (16,59) 1H-imidazole-1-carboxylate, (16,59) 2,3,5,6 -tetrachlor-4- (methylsulfonyl) pyridine, (16.60) 2,3-dibutyl-6-chlorothieno [2,3-d] pyrimidin-4 (3H) -one, (16.61) 2,6-dimethyl -1H, 5H- [1,4] dithino [2,3-c: 5,6-c '] dipyrous 1- 1,3,5,7 (2H, 6H) -tetrone, (16.62) 2- [5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] -1- (4- { 4- [(5R) -5-phenyl- 4,5-dihydro-1,2-oxazol-3-yl] -1,3-thiazol-2-yl} piperidin-1-yl) ethanone, (16 , 63) 2- [5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] -1- (4- {4- [(5S) -5-phenyl-4,5-dihydro- 1,2- oxazol-3-yl] -1,3-thiazol-2-yl} piperidin-1-yl) ethanone, (16.64) 2- [5-methyl-3- (trifluoromethyl) -1H-pyrazole -1-yl] -1- {4- [4- (5-phenyl-4,5-dihydro-1,2-oxazol-3-yl) -1,3-thiazol-2-yl] piperidin- 1-yl} ethanone, (16.65) 2-butoxy-6-iodo-3-propyl-4H-chromen-4-one, (16.66) 2-chloro-5- [2-chloro-1- ( 2,6- difluoro-4-methoxyphenyl) -4-methyl-1H-imidazol-5-yl] pyridine, (16.67) 2-phenylphenol and salts, (16.68) 3- (4,4,5- trifluoro- 3,3-dimethyl-3,4-dihydroisoquinolin-1-yl) quinoline, (16.69) 3,4,5-trichloropyridine-2,6-dicarbonitrile, (16.70) 3-chloro- 5- (4-chlorophenyl) -4- (2,6-difluorophenyl) -6-methylpyridazine, (16,71) 4- (4-chlorophenyl) -5- (2,6-difluorophenyl) -3,6-dimethylpyridazine , (16,72) 5-amino-1,3,4-thiadiazole-2-thiol, (16,73) 5-chloro-N'-phenyl-N '- (pro p-2-in-1-yl) thiophene-2-sulfonohydrazide, (16.74) 5-fluoro-2- [(4-fluorobenzyl) oxy] pyrimidine-4-amine, (16.75) 5-fluoro- 2- [(4-methylbenzyl) oxy] pyrimidine-4-amine, (16.76) 5-methyl-6-octyl [1,2,4] triazole [1,5-a] pyrimidine-7-amine, (16.77) (2Z) -3-amino-2-cyano-3-phenylacrylate, (16.78) N'- (4- {[3- (4-chlorobenzyl) -1,2,4- thiadiazol-5-yl] oxy} -2,5-dimethylphenyl) -N-ethyl-N-methylimidoformamide, (16.79) N- (4-chlorobenzyl) -3- [3-methoxy-4- (prop-2 -in-1-yloxy) phenyl] propanamide, (16.80) N- [(4-chlorophenyl) (cyano) methyl] -3- [3-methoxy-4- (prop-2-in-1-yloxy) phenyl] propanamide, (16.81) N- [(5-bromo-3-chloropyridin-2-yl) methyl] -2,4-dichloronicotinamide, (16.82) N- [1- (5-bromo-3 -chloropyridin-2-yl) ethyl] -2,4- dichloronicotinamide, (16.83) N- [1- (5-bromo-3-chloropyridin-2-yl) ethyl] -2-fluoro-4-iodonicotinamide, (16.84) N - {(E) - [(cyclopropylmethoxy) imino] [6- (difluoromethoxy) -2,3-difluorophenyl] methyl} -2-phenylacetamide, (16.85) N - {(Z) - [(cyclopropylmethoxy) imino] [6- (difluoromethoxy) -2,3-difluorophenyl] methyl} -2-f enylacetamide, (16.86) N '- {4- [(3- tert-butyl-4-cyano-1,2-thiazol-5-yl) oxy] -2-chloro-5-methylphenyl} -N-ethyl -N-methylimidoformamide, (16.87) N-methyl- 2- (1- {[5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] acetyl} piperidin-4-yl) -N- (1,2,3,4-tetrahydronaphthalen-1-yl) -1,3-thiazol-4-carboxamide, (16.88) N-methyl-2- (1- {[5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] acetyl} piperidin-4-yl) -N- [(1R) -1,2,3,4-tetrahydronaphthalen-1-yl] -1,3-thiazole - 4-carboxamide, (16.89) N-methyl-2- (1- {[5-methyl-3- (trifluoromethyl) -1H-pyrazol-1-yl] acetyl} piperidin-4-yl) -N- [(1S) -1,2,3,4-tetrahydronaphthalen-1-yl] -1,3-thiazol-4-carboxamide, (16.90) {6- [({[(1-methyl-1H -tetrazol-5-yl) (phenyl) methylene] amino} oxy) methyl] pyridin-2-yl} pentyl carbamate, (16.91) phenazine-1-carboxylic acid, (16.92) quinolin-8-ol , (16.93) quinolin-8-ol sulfate (2: 1), (16.94) {6- [({[(1-methyl-1H-tetrazol-5-yl) (phenyl) methylene] amino } oxy) methyl] pyridin-2-yl} tert-butyl carbamate, (16.95) 1-methyl-3- (trifluoromethyl) -N- [2'- (trifluoromethyl) biphenyl-2 -yl] -1H-pyrazol-4-carboxamide, (16.96) N- (4'-chlorobiphenyl-2-yl) -3- (difluoromethyl) -1-methyl-1H-pyrazol-4-carboxamide, (16 , 97) N- (2 ', 4'-dichlorobiphenyl-2-yl) -3- (difluoromethyl) -1-methyl-1H-pyrazol-4-carboxamide, (16.98) 3- (difluoromethyl) -1- methyl-N- [4'- (trifluoromethyl) biphenyl-2-yl] -1H-pyrazol-4-carboxamide, (16.99) N- (2 ', 5'-difluorobiphenyl-2-yl) -1-methyl -3- (trifluoromethyl) -1H-pyrazol-4-carboxamide, (16,100) 3- (difluoromethyl) -1-methyl-N- [4 '- (prop-1-in-1-yl) biphenyl-2-yl ] -1H-pyrazol-4-carboxamide, (16,101) 5-fluoro-1,3-dimethyl-N- [4 '- (prop-1-in-1-yl) biphenyl-2-yl] -1H-pyrazole -4-carboxamide, (16.102) 2-chloro-N- [4 '- (prop-1-in-1-yl) biphenyl-2-yl] nicotinamide, (16.103) 3- (difluoromethyl) -N- [4 '- (3,3-dimethylbut-1-in-1-yl) biphenyl-2-yl] -1-methyl-1H-pyrazol-4-carboxamide, (16,104) N- [4' - (3,3- dimethylbut-1-in-1-yl) biphenyl-2-yl] -5-fluoro-1,3-dimethyl-1H-pyrazol-4-carboxamide, (16.105) 3- (difluoromethyl) -N- (4'- ethinylbiphenyl-2-yl) -1-methyl-1H-pyrazol-4-carboxamide, (16.106) N- (4'-ethinylbiphenyl-2-yl) -5 -fluoro-1,3-dimethyl-1H-pyrazol-4-carboxamide, (16.107) 2-chloro-N- (4'- ethynylbiphenyl-2-yl) nicotinamide, (16.108) 2-chloro-N- [4 ' - (3,3-dimethylbut-1-in-1-yl) biphenyl-2-yl] nicotinamide, (16.109) 4- (difluoromethyl) -2-methyl-N- [4'- (trifluoromethyl) biphenyl-2- yl] -1,3-thiazol-5-carboxamide, (16,110) 5-fluoro-N- [4 '- (3-hydroxy-3-methylbut-1-in-1-yl) biphenyl-2-yl] - 1,3-dimethyl-1H-pyrazol-4-carboxamide, (16,111) 2-chloro-N- [4 '- (3-hydroxy-3-methylbut-1-in-1-yl) biphenyl-2-yl] nicotinamide, (16,112) 3- (difluoromethyl) -N- [4 '- (3-methoxy-3-methylbut-1-in-1-yl) biphenyl-2-yl] -1-methyl-1H-pyrazol-4 -carboxamide, (16,113) 5-fluoro-N- [4 '- (3-methoxy-3-methylbut-1-in-1-yl) biphenyl-2-yl] -1,3-dimethyl-1H-pyrazole- 4-carboxamide, (16,114) 2-chloro-N- [4 '- (3-methoxy-3-methylbut-1-in-1-yl) biphenyl-2-yl] nicotinamide, (16,115) (5-bromo- 2-methoxy-4-methylpyridin-3-yl) (2,3,4-trimethoxy-6-methylphenyl) methanone, (16,116) N- [2- (4- {[3- (4-chlorophenyl) prop-2 -in-1-yl] oxy} -3-methoxyphenyl) ethyl] -N2- (methylsulfonyl) valinamids, (16,117) 4-oxo acid -4- [(2-phenylethyl) amino] butanoic, (16,118) {6- [({[(Z) - (1-methyl-1H-tetrazol-5-yl) (phenyl) methylene] amino} oxy) methyl ] pyridin-2-yl} but-3-in-1-yl carbamate (16,119) 4-amino-5-fluoropyrimidin-2-ol (mesomeric form: 4-amino-5-fluoropyrimidin-2 (1H) -one ), (16,120) propyl 3,4,5-trihydroxybenzoate, (16,121) 1,3-dimethyl-N- (1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl ) -1H-pyrazol-4-carboxamide, (16,122) 1,3-dimethyl-N- [(3R) -1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl] -1H-pyrazol-4-carboxamide, (16,123) 1,3-dimethyl-N- [(3S) -1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl] - 1H-pyrazol-4-carboxamide, (16,124) [3- (4-chloro-2-fluorophenyl) -5- (2,4-difluorophenyl) -1,2-oxazol-4-yl] (pyridin-3-yl ) methanol, (16,125) (S) - [3- (4-chloro-2-fluorophenyl) -5- (2,4-difluorophenyl) -1,2-oxazol-4-yl] (pyridin-3-yl) methanol, (16,126) (R) - [3- (2-fluorophenyl-4-chloro) -5- (2,4-difluorophenyl) -1,2-oxazol-4-yl] (pyridin-3-yl) methanol , (16,127) 2- {[3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -2,4-dihydro-3H-1,2,4- triazol-3-thione, (16,128) 1- {[3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1H- 1,2,4-triazole thiocyanate -5-yl, (16,129) 5- (allylsulfanyl) -1- {[3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1H- 1,2, 4-triazole, (16,130) 2- [1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethyl-heptan-4-yl] -2,4-dihydro-3H-1 , 2,4-triazole-3-thione, (16,131) 2- {[rel (2R, 3S) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -2,4-dihydro-3H-1,2,4-triazole-3-thione, (16,132) 2- {[rel (2R, 3R) -3- (2-chlorophenyl) - 2- (2, 4-difluorophenyl) oxiran-2-yl] methyl} -2,4-dihydro-3H-1,2,4-triazol-3-thione, (16,133) 1- {[rel (2R, 3S) -3 - (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1H- 1,2,4-triazol-5-ylthocyanate, (16,134) 1- {[rel ( 2R, 3R) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1H-1,2,4-triazol-5-yl, (16,135) 5- (alylsulfanyl) -1- {[rel (2R, 3S) -3- (2-chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1H-1,2,4-triazole , (16,136) 5- (allylsulfanyl) -1- {[rel (2R, 3R) -3- (2 -chlorophenyl) -2- (2,4-difluorophenyl) oxiran-2-yl] methyl} -1H-1,2,4-triazole, (16,137) 2- [(2S, 4S, 5S) -1- (2 , 4-dichlorophenyl) -5-hydroxy-2,6,6-trimethyl-heptan-4-yl] -2,4-dihydro-3H-1,2,4-triazol-3-thione, (16,138) 2- [(2R, 4S, 5S) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethyl-heptan-4-yl] -2,4-dihydro-3H- 1,2,4- triazole-3-thione, (16,139) 2- [(2R, 4R, 5R) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethyl-heptan- 4-yl] -2,4-dihydro-3H-1,2,4-triazol-3-thione, (16,140) 2- [(2S, 4R, 5R) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethyl-heptan-4-yl] - 2,4-dihydro-3H-1,2,4-triazol-3-thione, (16,141) 2- [(2S , 4S, 5R) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethyl-heptan-4-yl] -2,4-dihydro-3H-1,2,4 -triazol-3-thione, (16,142) 2- [(2R, 4S, 5R) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6-trimethyl-heptan-4-yl] - 2,4-dihydro-3H-1,2,4-triazole-3-thione, (16,143) 2- [(2R, 4R, 5S) -1- (2,4-dichlorophenyl) -5-hydroxy- 2,6,6-trimethyl-heptan-4-yl] -2,4-dihydro-3H-1,2,4-triazole-3-thione, (16,144) 2- [(2S, 4R, 5S) -1- (2,4-dichlorophenyl) -5-hydroxy-2,6,6 -trimethyl-heptan-4-yl] -2,4-dihydro-3H-1,2,4-triazol-3-thione, (16,145) 2-fluoro-6- (trifluoromethyl) -N- (1, 1,3-trimethyl-2,3-dihydro-1H-inden-4-yl) benzamide, (16,146) 2- (6-benzylpyridin-2-yl) quinazoline, (16,147) 2- [6- (3 -fluoro-4-methoxyphenyl) -5-methylpyridin-2-yl] quinazoline, (16,148) 3- (4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl) quinoline, (16,149) abscisic acid.
[079] The active compounds according to the invention can additionally be combined with the microorganisms.
[080] Microorganisms, good tolerance provided by plants, toxicity with favorable homeothermia and good environmental compatibility, are suitable to protect plants and plant organs, to increase harvest yields, to improve the quality of harvested material and to control pests of animals, especially insects, arachnids, helminths, nematodes and molluscs, which are found in agriculture, horticulture, livestock, forests, gardens and leisure facilities, in the protection of stored products and materials, and in the hygiene sector . They can preferably be used in the form of crop protection compositions. They are active against normally sensitive and resistant species and against all or some stages of development. The microorganisms mentioned above include: microorganisms from the bacterial group, for example, Bacillus agri, Bacillus aizawai, Bacillus albolactis, Bacillus amyloliquefaciens, in particular, the B. amyloliquefaciens IN937a strain, or FZB42 strain, Bacillus cereus, in particular, spores of B. cereus, CNCM I-1562, Bacillus coagulans, Bacillus endoparasiticus, Bacillus endorhythmos, Bacillus firmus, spores, in particular, of B. firmus CNCM I-1582, Bacillus kurstaki, Bacillus lacticola, Bacillus lactimorbus, Bacillus lactis, Bacillus laterosporus , Bacillus lentimorbus, Bacillus licheniformis, Bacillus medusa, Bacillus megaterium, Bacillus metiens, Bacillus natto, Bacillus nigrificans, Bacillus popillae, Bacillus pumilus, in particular, the B. pumilus GB34 strain, Bacillus siamensis, Bacillus siamensis, Bacillus spiamusis, Bacillus spiamusis, Bacillus , the B. subtilis GB03 strain, or the B. subtilis var. amyloliquefaciens FZB24, Bacillus thuringiensis, in particular, B. thuringiensis var. israelensis or B. thuringiensis ssp. aizawai strain ABTS-1857 or B. thuringiensis ssp kurstaki HD-1, B. thuringiensis var. san diego, B. thuringiensis var. tenebrinos, Bacillus uniflagellatus, Delftia acidovorans, in particular, strain RAY209, Lysobacter antibioticus, in particular, strain 13-1, Metarhizium anisopliae, Pseudomonas clororaphis, in particular, strain MA342, Pseudomonas proradix, Streptomyces galleys, Streptomyces galbus, griseoviridis; microorganisms from the fungi group, for example, Ampelomyces quisqualis, in particular, strain AQ10, Aureobasidium pullulans, in particular, blastospores of strain DSM14940 or blastospores of strain DSM14941 or their mixtures, Beauveria bassiana, in particular strain ATCC74040, Beaui Candida oleophila, in particular, strain O, Coniothyrium minitans, in particular, strain CON / M / 91-8, Dilophosphora alopecuri, Gliocladium catenulatum, in particular strain J1446; Hirsutella thompsonii, Lagenidium giganteum, Lecanicillium lecanii (formerly known as Verticillium lecanii), in particular, strain conidia KV01, Metarhizium anisopliae, in particular, strain F52, Metschnikovia fructicola, in particular, NRRL strain Y-30752, NRRL strainer Musacea, PCR strain , in particular, strain QST20799, Nomuraea rileyi, Paecilomyces lilacinus, in particular, spores of strain of P. lilacinus 251, Penicillium bilaii, in particular strain ATCC22348, Pichia anomala, in particular strain WRL-076, Pseudozyma flocculosa, in particular , strain PF-A22 UL, Pytium oligandrum DV74, Trichoderma asperellum, in particular, strain ICC012, Trichoderma harzianum, insbesondere T. harzianum T39, Verticillium lecanii, in particular, the strains DAOM198499 and DAOM216596; insecticide microorganisms from the group of protozoa, for example, Nosema locustae, Vairimorpha; insecticide microorganisms from the virus group, for example, nuclear polyhedrosis virus (NPV) of the Gypsy moth (Lymantria dispar), NPV of the Tussock moth (Lymantriidae), Heliothis NPV, NPV Pine sawfly (Neodiprion), granulose virus (GV) Codling moth (Cydia pomonella); microorganisms from the entomopathogenic nematode group, for example, Steinernema scapterisci, Steinernema feltiae (Neoaplectana carpocapsae), Heterorhabditis heliothidis, Xenorhabdus luminescence.
[081] The active compounds identified here by their common names are known and are described, for example, in the pesticide manual ("The Pesticide Manual" 14th Ed, British Crop Protection Council, 2006) or can be found on the internet (for example , http://www.alanwood.net/pesticides).
[082] All partners of the mixtures mentioned in classes (1) to (16) can, if they are able, based on their functional groups, optionally form salts with suitable bases or acids.
[083] Finally, it was found that the new compounds of formula (I), while being well tolerated by plants, with toxicity with favorable homeothermia and good environmental compatibility, are especially suitable for combating animal pests, especially those arthropods, insects, arachnids, helminths, nematodes and molluscs, which are found in agriculture, in forests, in the protection of stored products and materials and in the hygiene sector or in the animal health sector. The compounds according to the invention can also be used in the animal health sector, for example, for the control of endo- and / or ectoparasites.
[084] The compounds according to the invention can be used as agents to combat animal parasites, preferably as crop protection agents. They are active against normally sensitive and resistant species and against all or some stages of development.
[085] The compounds according to the invention can be converted into generally known formulations. In general, such formulations comprise 0.01-98% by weight of active compound, preferably between 0.5 and 90% by weight.
[086] The compounds according to the invention can be available and in the forms of use prepared from these formulations, as a mixture with other active compounds or synergists. Synergistic agents are compounds that increase the action of active substances, without any need for the added synergist to be active in them.
[087] The content of the active compound in the forms of use prepared from commercially available formulations can vary within wide limits. The concentration of the active compound in the application forms of the active compound can be from 0.00000001 to 95% by weight of active compound, preferably 0.00001-1% by weight.
[088] The compounds are employed in a usual manner suitable for the forms of use.
[089] All plants and plant parts can be treated according to the invention. Plants, in this context, are understood to include all plants and plant populations, such as desired and unwanted wild plants or crop plants (including naturally occurring crop plants). Cultivated plants can be plants that can be obtained by conventional breeding and optimization methods or by biotechnological and genetic methods or combinations of these methods, including transgenic plants and including plant varieties that may or may not be protected by variety property rights. vegetable. Plant parts should be understood in the sense of everyone above ground and below ground plant parts and organs, such as twig, leaf, flower and root, examples that can be mentioned being leaves, thin leaves, stems, trunks, flowers, fruit bodies, fruits and seeds and also roots, tubers and rhizomes. Plant parts also include harvest material and material for vegetative and generative propagation, for example, cuttings, tubers, rhizomes, strips and seeds.
[090] The treatment, according to the invention, of plants and parts of plants with the active compounds is carried out directly or by allowing action on the surrounding space, habitat or storage space of them, by current treatment methods, for example , by immersion, spraying, evaporation, nebulization, dispersion, apply over, injection, and, in the case of propagating material, in particular, in the case of seeds, by applying one or more layers of coating.
[091] As already mentioned above, it is possible to treat all plants and their parts according to the invention. In a preferred embodiment, species of wild plants and varieties of plants, or those obtained by conventional methods of biological reproduction, such as crossing or fusing protoplasts, as well as their parts, are treated. In another preferred embodiment, transgenic plants and plant varieties obtained by genetic engineering methods, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof, are treated. The terms "parts" and "parts of plants" or "parts of plants" have been elucidated above.
[092] More preferably, plants of the plant varieties that are, each commercially available or in use, are treated according to the invention. Plant varieties should be understood as meaning plants having new properties ("characteristics") and which have been obtained by conventional methods of reproduction, mutagenesis or by recombinant DNA techniques. They can be cultivars, biotypes and genotypes.
[093] In the animal health sector, that is, in the field of veterinary medicine, the active compounds according to the present invention act against animal parasites, especially ectoparasites or, in another modality, also endoparasites. The term "endoparasite" includes especially helminths, such as cestodes, nematodes or trematodes and protozoa, such as coccidia. Ectoparasites are typically and, preferably, arthropods, especially insects, such as flies (biting and licking), parasitic fly larvae, lice, hair lice, bird lice, fleas and the like; or mites such as ticks, for example, hard-shelled ticks or soft-shelled ticks, or mites, such as scabies mites, harvesting mites, bird mites and the like, and also aquatic ectoparasites, such as copepods.
[094] These parasites include: of the order of Anoplurida, for example, Haematopinus spp., Linognathus spp., Pediculus spp., Phthirus spp. and Solenopotes spp .; specific examples are: Linognathus setosus, Linognathus vituli, Linognathus ovillus, Linognathus oviformis, Linognathus pedalis, Linognathus stenopsis, Haematopinus asini macrocephalus, Haematopinus eurysternus, Haematopinus suis, Pediculus humanus capis, Phenus of the order of Mallophagida and the suborders of Amblycerina and Ischnocerina, for example, Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp. and Felicola spp .; specific examples are: Bovicola bovis, Bovicola ovis, Bovicola limbata, Damalina bovis, Trichodectes canis, Felicola subrostratus, Bovicola caprae, Lepikentron ovis, Werneckiella equi; of the order of Diptera and the sub-orders Nematocerina and Brachycerina, for example, Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Odagmia spp., Wilhelmia spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp. ., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp. Melophagus spp., Rhinoestrus spp., Tipula spp .; specific examples are: Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles gambiae, Anopheles maculipennis, Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Fannia canicularis, Sarcophaga, Tipia sericata, Simulium reptans, Phlebotomus papatasi, Phlebotomus longipalpis, Odagmia ornata, Wilhelmia equina, Boophthora erythrocephala, Tabanus bromius, Tabanus spodopterus, Tabanus atratus, Tabanus sudeticus, Hybomitrausurichisopsis, chrysotaopsurea, Chrysota, citricus Musca domestica, Haematobia irritans irritans, Haematobia irritans exigua, Haematobia stimulans, Hydrotaea irritans, Hydrotaea albipuncta, Chrysomya cloropyga, Chrysomya bezziana, Oestrus ovis, Hypoderma bovis, Hypoderma lineatum, Przhevalskiana, Lipz, lipis, Henna, Lipis, lipis, Henna, Henna Hippobo sca variegata, Hippobosca equina, Gasterophilus intestinalis, Gasterophilus hemorrhoal, Gasterophilus inermis, Gasterophilus nasalis, Gasterophilus nigricornis, Gasterophilus pecorum, Braula coeca; from the order of Siphonapterida to, for example, Pulex spp., Ctenocephalides spp., Tunga spp., Xenopsylla spp., Ceratophyllus spp .; specific examples are: Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; from the order of Heteropterida, for example, Cimex spp., Triatoma spp., Rhodnius spp. and Panstrongylus spp .; from the order of Blattarida, for example, Blatta orientalis, American Periplaneta, Blattela germanica and Supella spp. (for example, Suppella longipalpa); the subclass of Acari (Acarina) and the orders of meta- and Mesostigmata, for example, Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Dermanyssus spp., Rhipicephalus spp. (the original genus of ticks with multiple hosts), Ornithonyssus spp., Pneumonyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp., Acarapis spp .; specific examples are: Argas persicus, Argas reflexus, Ornithodorus moubata, Otobius megnini, Rhipicephalus (Boophilus) microplus, Rhipicephalus (Boophilus) decoloratus, Rhipicephalus (Boophilus) annulatus, Rhipicephalus (Boophilus) Hyacatomomomomum, Hyalomalomalum, Hyalomalum, Hyalomalomum, Hyalomalom transiens, Rhipicephalus evertsi, Ixodes ricinus, Ixodes hexagonus, Ixodes canisuga, Ixodes pilosus, Ixodes rubicundus, Ixodes scapularis, Ixodes holocyclus, Haemaphysalis concinna, Haemaphysalis punctata, Haemaphysisisisisisisisisisisisysisisismaysalis, haisphysisisis Dermacentor pictus, Dermacentor albipictus, Dermacentor andersoni, Dermacentor variabilis, Hyalomma mauritanicum, Rhipicephalus sanguineus, Rhipicephalus bursa, Rhipicephalus appendiculatus, Rhipicephalus capensis, Rhipicepmaus ambisomomis, Ambient mum, Rothicephalus turanicus, Ambient mum latum, Amblyomma hebraeum, Amblyomma cajennense, Dermanyssus gallinae, Ornithonyssus bursa, Ornithonyssus sylviarum, Varroa jacobsoni; of the order of Actinedida (Prostigmata) and Acaridida (Astigmata), for example, Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp. ., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Cytodites spp. specific examples are: Cheyletiella yasguri, Cheyletiella blakei, Demodex canis, Demodex bovis, Demodex ovis, Demodex caprae, Demodex equi, Demodex caballi, Demodex suis, Neotrombicula autumnalis, Neotrombicula desaleri, Neoschongastia, Tumeric, Mastic canis, Sarcoptes bovis, Sarcoptes ovis, Sarcoptes rupicaprae (= S. caprae), Sarcoptes equi, Sarcoptes suis, Psoroptes ovis, Psoroptes cuniculi, Psoroptes equi, Chorioptes bovis, Psoergates ovis, Pneumonyssoidic mange, Pneumonisisisis mane, Pneumon the subclass of copepods with the order of Siphonostomatoida, in particular, to the genera Lepeophtheirus and Caligus; the species Lepeophtheirus salmonis, Caligus elongatus and Caligus clemensi can be mentioned by way of example and with particular preference.
[095] The active compounds according to the invention are also suitable for the control of arthropods, helminths and protozoa that attack animals. Animals include agricultural livestock, for example, cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, captive fish, bees. Animals also include domestic animals - also known as pets - for example, dogs, cats, cage birds, aquarium fish, and which are known as test animals, for example, hamsters, guinea pigs, rats and mice.
[096] The control of these arthropods - or, in another modality, also helminths and / or protozoa - should reduce cases of death and improve yield (for meat, milk, wool, skins, eggs, honey, etc.) and health of the host animal, and therefore the use of the active compounds according to the invention allows the creation of animals more economically viable and easier.
[097] For example, it is desirable to prevent or interrupt the host's blood absorption by the parasites (if applicable). Parasite control can also contribute to the prevention of the transmission of infectious substances.
[098] The term "control", as used here, with regard to the field of animal health means that the active compounds act by reducing the occurrence of the parasite in question, in an animal infested with these parasites to a harmless level. More specifically, "control", as used herein, means that the active compound kills the parasite in question, slows its growth or inhibits its proliferation.
[099] In general, the active compounds according to the invention can be used directly, when they are used for the treatment of animals. They are preferably used in the form of pharmaceutical compositions which can comprise pharmaceutically acceptable and / or auxiliary excipients known in the art.
[100] In the animal health and livestock sector, the active compounds are used (administered) in a known way, by enteral administration in the form of, for example, tablets, capsules, potions, liquid medicines, granules, pastes, boluses, process through food and suppositories, by parenteral administration, for example, by injection (intramuscular, subcutaneous, intravenous, intraperitoneal among others), implants, by nasal administration, through dermal administration in the form, for example, of immersion or bath , spraying, pouring over and staining over, washing and powdering powder, and also with the aid of molded articles containing the active compound, such as collars, identification marks on the animals 'ears, identification marks on the animals' tail, bandages members, halters, marking devices, etc. The active compounds can be formulated in the form of a shampoo or as suitable formulations applicable in aerosols or non-pressurized sprayers, for example, pump sprayers and atomizing sprayers.
[101] In the case of use for livestock, poultry, domestic animals, etc., the active compounds according to the invention can be used as formulations (for example, powders, wet powders ["WP"], emulsions, concentrates emulsifiable ["CE"], free-flow compositions, homogeneous solutions and suspension concentrates ["SC"]), which contain the active compounds in an amount of 1 to 80% by weight, directly or after dilution (for example, dilutions of 100 to 10000 times), or they can be used as a chemical bath.
[102] In the case of use in the animal health sector, the active compounds according to the invention can be used in combination with suitable synergistic agents, repellents or other active compounds, for example, insecticides, acaricides, anthelmintics, agents anti-protozoa in order to broaden the spectrum of activity. Potential mixing components for the compounds of the formula (I) according to the invention for animal health applications can be one or more compounds from the groups of active compounds listed on pages 29 (from line 33 onwards) to page 41 ( line 17). Here, the selection sequence or, in addition, the following active compounds is / are particularly suitable for use in mixtures for applications in the animal health sector: from the group of acetylcholinesterase inhibitors (AChE): from the group of carbamates , bendiocarb, carbaryl, metomil, promacil and propoxur can be mentioned here as being particularly preferred for applications against ectoparasites; or from the group of the organophosphates, azametiphos, chlorfenvinfos, chlorpyrifos, coumafos, citioato, diazinon (dimpilato), dichlorvos (DDVP), dicrotofos, dimetoato, etion (dietion), famfur (famofos), fenitrotion, heention (MPP) , malation, nalede, fosmete (PMP, phthalophos) foxim, propetanfos, temefos, tetrachlorvinfos (CMV) and trichlorfon / metrifonate can be mentioned here as being particularly preferred for applications against ectoparasites; from the group of GABA-dependent chloride channel antagonists: from the group of organochlorine compounds, endosulfan (alpha-) and lindane can be mentioned here as being particularly preferred for applications against ectoparasites; or from the group of fiprols (phenylpyrazoles), for example, acetoprol, etiprol, fipronil, pirafluprol, pyriprol and rizazole, fipronil and pyriprol can be mentioned here as being particularly preferred for applications against ectoparasites; or from the group of arylisoxazolines, arylpyrrolines, arylpyrrolidines, for example, fluralaner (known from WO2009 / 2024541, Ex 11-1;., but also compounds from WO2012007426, WO2012042006, WO2012042007, WO2012107533, WO201201201535, WO2012165186, WO2012165186, , WO2012127347, WO2012038851, WO2012120399, WO2012156400, WO2012163959, WO2011161130, WO2011073444, WO2011092287, WO2011075591, WO2011157748, WO 2007/075459, WO 2007/125984, WO 2005/085216, WO 2009/200249), WO 2009/002809) and structurally related arylpyrrolines (known, for example, from WO2009 / 072621, WO 2010020522, WO 2009112275, WO 2009097992, WO 2009072621, JP 2008133273, JP 2007091708), or arylpyrrolidines (for example, WO2012004326, WO2012035011, WO20120455000, WO201204550 , WO 2010043315, WO 2008128711, JP 2008110971), afoxolaner and fluaralaner can be mentioned here as being particularly preferred for applications against ectoparasites; or from the group of the so-called methadiamides (known, for example, from WO2012020483, WO2012020484, WO2012077221, WO2012069366, WO2012175474, WO2011095462, WO2011113756, WO2011093415, WO2005073165); from the group of sodium channel modulators / voltage-dependent sodium channel blockers: from the group of pyrethroids, the pyrethroids aletrine type I, bioalethrin, permethrin, phenothrin, resmethrin, tetramethrin and type pyrethroids ( alpha-cyanopyrethroids) alpha-cypermethrin, cyfluthrin (beta-), cyhalothrin (lambda-), cypermethrin (alpha-, zeta-), deltamethrin, fenvalerate, flucitrinate, flumethrin, fluvalinate (tau-), and etofenprox ester-free pyrethroids and etofenprox ester may be mentioned here as being particularly preferred for applications against ectoparasites; the active compounds in this class are very, particularly, suitable as mixing components, since they have a longer-lasting repelling contact action and therefore add this component to the activity spectrum; from a group of nicotinergic acetylcholine receptor agonists, clothianidin, dinotefuran, imidacloprid, nitenpiram, and thiacloprid, or nicotine or flupiradifurone, may be mentioned here as being particularly preferred for applications against ectoparasites; from the group of allosteric acetylcholine receptor modulators (agonists), spinosad and spininam can be mentioned here as being particularly preferred for applications against ectoparasites; from the group of chloride channel activators, doramectin, eprinomectin, milbemycin oxime, moxidectin, selamectin and nodulisporic acid A can be mentioned here as being particularly preferred for applications against ectoparasites; from a group of analogs of juvenile hormones, for example, hydroprene (S-), quinoprene, methoprene (S-); or phenoxycarb; pyriproxifene; methoprene (S-) and pyriproxifene can be mentioned here as being particularly preferred for applications against ectoparasites; from the group of mite growth inhibitors, ethoxazole can be mentioned here as being particularly preferred for applications against ectoparasites; from the group of Slo-1- and latrophilin receptor agonists, such as cyclic depsipeptides, for example, emodepside and its precursor PF1022A (known from EP 382173, compound I), emodepside can be mentioned here as being particularly preferred here for applications against ectoparasites; from the group of inhibitors of chitin biosynthesis, type 0, such as benzoylureas, diflubenzuron, fluazuron, lufenuron and triflumuron can be mentioned here as being particularly preferred for applications against ectoparasites; from the group of switches in a molting phase, cyromazine and dicyclanil can be mentioned here as being particularly preferred for applications against ectoparasites; from the group of octopaminergic agonists, amitraz, cimiazole and demiditraz can be mentioned here as being particularly preferred for applications against ectoparasites; from the group of electron transport inhibitors of the complex I, such as from the group of acaricides METI, fenpyroximate, pyrimidifene and tolfenpirade can be mentioned here as being particularly preferred for applications against ectoparasites; from the group of tension-dependent sodium channel blockers, indoxacarb and metaflumizone can be mentioned here as being particularly preferred for applications against ectoparasites; from the group of acetyl-CoA carboxylase inhibitors, such as tetronic acid derivatives or tetramic acid derivatives, spirodiclofen and spiromesifene and also spirotetramate can be mentioned here as being particularly preferred for applications against ectoparasites; from the group of effectors of the ryanodine receptor, flubendiamide, Rinaxipir and Ciazipir can be mentioned here as being particularly preferred for applications against ectoparasites; from the group of effectors having an unknown mechanism of action, in particular, mention may be made of 1- (3-chloropyridin-2-yl) -N- [4-cyano-2-methyl-6- (methylcarbamoyl) phenyl ] -3- {[5- (trifluoromethyl) -2H-tetrazol-2-yl] methyl} -1H-pyrazol-5-carboxamide (known from WO2010 / 069502); from the group of synergistic agents that can be used to further improve activity, MGK264 (N-octylbicycloheptenecarboxamide), piperonyl butoxide (PBO) and verbutin can be mentioned here as being particularly preferred for applications against ectoparasites.
[103] In addition to these groups, it is also possible to use short-term repellents in mixtures or a combined application. Examples are DEET (N, N-diethyl-3-methylbenzamide), icaridine (1-piperidinecarboxylic acid), (1S, 20S) -2-methylpiperidinyl-3-cyclohexene-1-carboxamide (SS220), indalone (3,4- butyl dihydro-2,2-dimethyl-4-oxo-2H-pyran-6-carboxylate), dihydronepetalactones, nootkatone, IR3535 (3- [N-butyl-N-acetyl] - aminopropionic acid ester ), 2-ethylhexane-1,3-diol, (1R, 2R, 5R) -2- (2-hydroxypropan-2-yl) -5-methyl-cyclohexan-1-ol, benzene-1, Dimethyl 2-dicarboxylate, dodecanoic acid, undecan-2-one, N, N-diethyl-2-phenylacetamide and essential oils or other plant ingredients of known repellent action, such as, for example, borneol, calicarpenal, 1,8 -cineol (eucalyptol), carvacrol, b-citronelol, a-copaene, coumarin (or its synthetic derivatives known from US20120329832). Icaridine, indalone and IR3535 (3- [N-butyl-N-acetyl] -aminopropionic acid ethyl ester) are particularly preferred for use against ectoparasites.
[104] From the groups (I-1) to (I-25) mentioned above, the following groups are preferred as mixing components: (I-2), (I-3), (I-4), (I-5), (I-6), (I-17), (I-25).
[105] Very particularly preferred examples of active insecticidal or acaricidal compounds, synergistic agents or repellents as mixing components for the compounds of the formula (I) according to the invention are afoxolaner, alethrin, amitraz, bioalectrin, clothianidin, cyfluthrin (beta -), cyhalothrin (lambda-), cyimiazole, cypermethrin (alpha-, zeta-), cyphenothrin, deltamethrin, demiditraz, dinotefuran, doramectin, eprinomectin, etofenprox, fenvalerate, fipronil, fluazuron, flucitrinate, flucitrinate, flucitrinate, flucinate ), icaridine, imidacloprid, ivermectin, MGK264, milbemycin oxime, moxidectin, nitenpiram, permethrin, phenothrin, piperonyl butoxide, pyriprol, resmethrin, selamectin, silafluofen, espinetoram, espinosade, tetramethrin, tetramethrin.
[106] The compounds according to the invention have also been found to have a strong insecticidal action against insects that destroy industrial materials. Industrial materials in the present context are understood as inanimate materials, as preferably, plastics, adhesives, glues, papers and cards, leather, wood, processed wood products and coating compositions.
[107] In addition, the compounds according to the invention can be used as antifouling compositions, alone or in combinations with other active compounds.
[108] The active compounds are also suitable for the control of animal parasites in the domestic sector, in the hygiene sector and in the protection of stored products, especially insects, arachnids and mites, which are found in closed spaces, such as, for example, homes, manufacturing facilities, offices, vehicle cabins and the like. They can be used to control these pests, alone or in combination with other active and auxiliary compounds, in household insecticide products. They are effective against sensitive and resistant species, and against all stages of development.
[109] Plants should be understood in the sense of all plant species, plant varieties and plant populations, such as desired and unwanted wild plants or cultivation plants. Cultivation plants being treated according to the invention are naturally occurring plants or those that were obtained by conventional methods of reproduction and optimization, or by biotechnological and recombinant methods or by combining the methods mentioned above. The term plant crop means, of course, also to include transgenic plants.
[110] Plant varieties should be understood to mean plants having new properties (characteristics) and which have been obtained by conventional breeding, mutagenesis or by recombinant DNA techniques or a combination of these. They can be cultivars, varieties, bio- or genotypes.
[111] Plant parts are understood to mean all plant parts and organs above and below ground, such as twig, leaf, flower and root, in particular leaves, fine leaves, stems, trunks, flowers, fruit bodies, fruits, seeds, roots, tubers and rhizomes. The term "plant parts" also includes harvest material and material for vegetative and generative propagation, for example, cuttings, tubers, rhizomes, strips and seeds.
[112] In a preferred embodiment, naturally occurring plant species and plant varieties, or those obtained through conventional methods of reproduction and optimization (for example, crossing or fusion of protoplasts), as well as plant parts of these , are treated.
[113] In another embodiment according to the invention, transgenic plants obtained by genetic engineering methods, if appropriate, in combination with conventional methods, and parts thereof, are treated.
[114] The treatment method according to the invention is preferably used for genetically modified organisms, such as, for example, plants or parts of plants.
[115] Genetically modified plants, known as transgenic plants, are plants in which a heterologous gene has been stably integrated into the genome.
[116] The term "heterologous gene" essentially means a gene that is supplied or assembled outside the plant and, when introduced into the nuclear, chloroplastic or mitochondrial genome provides the transformed plant with new or improved agronomic or other properties by expressing a protein or polypeptide of interest or by down-regulating or silencing another gene / other genes that are / are present in the plant (using, for example, antisense technology, co-suppression technology or RNA interference technology [RNAi]). A heterologous gene that is present in the genome is also called a transgene. A transgene that is defined by its particular location in the plant's genome is called a genetic transformation or modification.
[117] Depending on the species of plants or varieties of plants, their location and growing conditions (soil, climate, vegetation period, diet), the treatment according to the invention can also result in ("synergistic") effects superadditives. For example, the following effects that go beyond the effects that can be expected, in fact, are possible: reduced rates of application and / or broader spectrum of activity and / or increased effectiveness of active compounds and compositions that can be used according to the invention, better plant growth, greater tolerance to high or low temperatures, greater tolerance to drought or water or soil salinity, increased flowering performance, easier harvesting, accelerated ripening, higher harvest yields, larger fruits , higher plant height, greener leaf color, early flowering, higher quality and / or a higher nutritional value of the harvested products, higher concentration of sugar within the fruits, better storage and / or processing stability of the harvested products.
[118] At certain application rates, combinations of active compounds according to the invention can also have a strengthening effect on plants. Therefore, they are also suitable for mobilizing the plant's defense system against the attack of unwanted phytopathogenic fungi and / or microorganisms and / or viruses. This can optionally be one of the reasons for increasing the activity of the combinations according to the invention, for example, against fungi. Plant reinforcing substances (resistance inducers) are also to be understood as meaning, in the present context, substances or combinations of substances that are capable of stimulating the defense system of plants in such a way that, when subsequently inoculated with fungi unwanted phytopathogens and / or microorganisms and / or viruses, the treated plants exhibit a substantial degree of resistance to these unwanted phytopathogenic fungi and / or microorganisms and / or viruses. In the present case, phytopathogenic fungi and / or unwanted microorganisms and / or viruses are understood to mean phytopathogenic fungi, bacteria and viruses. The substances according to the invention can therefore be used to protect plants from attack by the mentioned pathogens within a certain period of time after treatment. The period of time in which protection is carried out, usually extends from 1 to 10 days, preferably from 1 to 7 days, after the treatment of the plants with the active compounds.
[119] Plants that are additionally preferably treated according to the invention are resistant to one or more factors of biotic stress, that is, said plants have a better defense against animal pests and microbial pests, such as nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and / or viroids.
[120] In addition to the plants and plant varieties mentioned above, it is also possible to treat those according to the invention, which are resistant to one or more abiotic stress factors.
[121] Abiotic stress conditions may include, for example, drought, exposure to cold temperature, exposure to heat, osmotic stress, flooding, increased soil salinity, increased exposure to minerals, exposure to ozone, exposure to strong light, limited availability of nitrogenous nutrients, limited availability of phosphorus nutrients or shade precautions.
[122] The plants and varieties of plants that can also be treated according to the invention are those plants characterized by characteristics of improved production. Enhanced yield in these plants may be the result of, for example, improved plant physiology, improved plant growth and improved development, such as water use efficiency, water retention efficiency, improved nitrogen use, increased carbon assimilation, improved photosynthesis, increased germination efficiency and accelerated maturation. Yield can also be affected by better plant architecture (conditions under stress and non-stress), including early flowering, flowering control for hybrid seed production, seedling vigor, plant size, the number and distance of internode, the root growth, seed size, fruit size, pod size, pod or ear number, number of seeds per pod or ear, seed mass, improved seed supplement, reduced seed dispersion, reduced pod dehiscence and resistance to accommodation. Other characteristics of seed composition, such as protein content, oil content and oil composition, nutritional value, reduction of anti-nutritional compounds, better processing capacity and better storage stability.
[123] The plants that can be treated according to the invention are hybrid plants that already express the characteristic of heterosis or hybrid vigor, which generally results in greater production, vigor, health and resistance to biotic and abiotic stress. Such plants are usually made by crossing a pure male sterile parent line (female parent) with another pure male fertile parent line (male parent). Hybrid seed is typically harvested from sterile male plants and sold to producers. Sterile male plants can sometimes (for example, maize) be produced by removing the tassel, (ie, the mechanical removal of the male reproductive organs or male flowers), but more typically, male sterility is the result of determinants in the plant genome. In that case, and especially, when the seed is the desired product to be harvested from hybrid plants, it is typically useful to ensure that male fertility in hybrid plants, which contain the genetic determinants responsible for male sterility, is completely restored. This can be achieved to ensure that male parents have appropriate fertility restoring genes that are capable of restoring male fertility in hybrid plants that contain the genetic determinants responsible for male sterility. The genetic determinants for male sterility can be located in the cytoplasm. Examples of cytoplasmic male sterility (CMS) have been described, for example, for Brassica species. However, the genetic determinants for male sterility can also be located in the nuclear genome. Sterile male plants can also be obtained by methods of plant biotechnology, such as genetic engineering. A particularly useful means of obtaining plants with male sterility is described in WO 89/10396, in which, for example, a ribonuclease, such as barnase, is selectively expressed in tapetum cells in the stamens. Fertility can be restored by expression in the tapetum cells of a ribonuclease inhibitor such as barstar.
[124] The plants or plant varieties (obtained by plant biotechnology methods, such as genetic engineering) that can be treated according to the invention are plants tolerant to herbicides, that is, plants made tolerant to one or more herbicides provided. Such plants can be obtained either by genetic transformation, or by selecting plants containing a mutation, giving tolerance to herbicides.
[125] Herbicide-tolerant plants are, for example, glyphosate-tolerant plants, that is, plants made tolerant to the glyphosate herbicide or its salts. Thus, for example, glyphosate-tolerant plants can be obtained by transforming the plant with a gene that encodes the synthase of the enzyme 5-enolpyruvylchiquime-3-phosphate (EPSPS). Examples of such EPSPS genes are the AroA gene (CT7 mutant) from the bacterium Salmonella typhimurium, the CP4 gene from the bacterium Agrobacterium sp., The genes encoding a petunia EPSPS, a tomato EPSPS, or an Eleusine EPSPS. It can also be a mutated EPSPS. Glyphosate-tolerant plants can also be obtained by expressing a gene encoding a glyphosate oxidoreductase enzyme. Glyphosate-tolerant plants can also be obtained by expressing a gene that encodes a glyphosate acetyl transferase enzyme. Glyphosate-tolerant plants can be obtained by selecting plant mutations from the aforementioned genes that occur naturally.
[126] Other herbicide-resistant plants are, for example, plants that have been made tolerant to herbicides that inhibit the enzyme glutamine synthase, such as bialafos, phosphinothricin or glufosinate. Such plants can be obtained by expression of a detoxifying enzyme of the herbicide or a mutant of the enzyme glutamine synthase that is resistant to inhibition. Such an efficient detoxifying enzyme is, for example, an enzyme that encodes a phosphinothricin acetyltransferase (for example, the bar or pat protein from Streptomyces species, for example). Plants that express an exogenous phosphinothricin acetyltransferase have been described.
[127] Other herbicide-tolerant plants are also plants that have been made tolerant to herbicides that inhibit the enzyme hydroxyphenylpyruvate dioxigenase (HPPD). Hydroxyphenylpyruvate dioxigenases are enzymes that catalyze the reaction in which parahydroxyphenylpyruvate (HPP) is converted to homogentisate. Plants tolerant to HPPD inhibitors can be transformed with a gene encoding a naturally occurring resistant HPPD enzyme, or a gene encoding a mutated HPPD enzyme. Tolerance to HPPD inhibitors can also be obtained by transforming plants with genes that encode certain enzymes allowing the formation of homogentisate despite the inhibition of the native HPPD enzyme by the HPPD inhibitor. Plant tolerance to HPPD inhibitors can also be improved by transforming plants with a gene encoding a prephenate dehydrogenase enzyme in addition to a gene encoding a tolerant HPPD enzyme.
[128] Other herbicide-resistant plants are plants that have been made tolerant to acetolactate synthase (ALS) inhibitors. Known ALS inhibitors include, for example, sulfonylurea herbicides, imidazolinone, triazolopyrimidines, pyrimidinyl oxy (thio) benzoates and / or sulfonylaminocarbonyltriazolinone. Different mutations in the ALS enzyme (also known as acetohydroxy acid synthase, AHAS) are known to confer tolerance to different herbicides and groups of herbicides. The production of sulfonylurea tolerant plants and imidazolinone tolerant plants has been described in the international publication WO 1996/033270. Plants tolerant to sulfonylurea and imidazolinone have also been described, for example, in WO 2007/024782.
[129] Other imidazolinone and / or sulfonylurea tolerant plants can be obtained by induced mutagenesis, selection in cell cultures in the presence of the herbicide or reproductive mutation.
[130] The plants or varieties of plants (obtained by methods of plant biotechnology, such as genetic engineering) that can also be treated according to the invention are transgenic plants resistant to insects, that is, plants made resistant to attacks by certain insects target. Such plants can be obtained by genetic transformation, or by selecting plants that contain a mutation conferring resistance to such insects.
[131] The term "insect resistant transgenic plant" as used herein includes any plant that contains at least one transgene comprising a coding sequence that encodes: 1) a crystalline insecticidal protein from Bacillus thuringiensis or an insecticidal part thereof , such as the crystalline insecticidal proteins compiled online at: http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/, or parts of the insecticides thereof, for example, proteins of the Cry classes of Cry1Ab proteins , Cry1Ac, Cry1F, Cry2Ab, Cry3Ae, or Cry3Bb or insecticidal portions thereof; or 2) a crystal protein from Bacillus thuringiensis or a portion thereof that is insecticidal in the presence of a second other crystalline protein from Bacillus thuringiensis, or a portion thereof, such as the binary toxin consisting of Cry34 and Cry35 crystalline proteins; or 3) a hybrid insecticidal protein comprising parts of two different insecticidal crystalline proteins from Bacillus thuringiensis, such as a hybrid of the proteins of 1) above or a hybrid of the proteins of 2) above, for example, the Cry1A.105 protein produced by event MON98034 of corn (WO 2007/027777); or 4) a protein from any of points 1) to 3) above, where some, in particular, 1 to 10 amino acids have been replaced by other amino acids to obtain greater insecticidal activity for a target species of insects, and / or for expand the range of affected target insect species, and / or because of changes induced in the coding DNA during cloning or transformation, such as the Cry3Bb1 protein in corn MON88017 or MON863 events, or the Cry3A protein in the MIR 604 event of corn; 5) an insecticidal secreted protein from Bacillus thuringiensis or Bacillus cereus, or a portion of the same insecticide, such as the vegetative insecticidal (VIP) proteins listed at: http://www.lifesci.sussex.ac.uk/Home / Neil_Crickmore / Bt /vip.html, for example, proteins of the VIP3Aa protein class; or 6) a protein secreted from Bacillus thuringiensis or Bacillus cereus, which is insecticidal in the presence of a second protein secreted from Bacillus thuringiensis or B cereus, such as the binary toxin consisting of VIP1A and VIP2A proteins; 7) a hybrid insecticidal protein comprising parts of different proteins secreted from Bacillus thuringiensis or Bacillus cereus, as a hybrid of the proteins in 1) above or a hybrid of the proteins in 2) above; or 8) a protein from any of points 1) to 3) above, where some, particularly 1 to 10, amino acids have been replaced by other amino acids to obtain greater insecticidal activity for target insect species, and / or to expand the range of affected species of target insects, and / or because of changes induced in the coding DNA during cloning or transformation (while still encoding an insecticidal protein), such as the VIP3Aa protein in the COT 102 event on cotton.
[132] Of course, a transgenic insect-resistant plant, as used herein, also includes any plant that comprises a combination of genes encoding the proteins of any of the above classes 1 to 8. In one embodiment, an insect-resistant plant contains more than one transgene that encodes a protein from any of the previous classes 1 to 8, to expand the range of affected target insect species, or to delay the development of insect resistance to plants through different insecticidal proteins for the same target insect species, but with a different mode of action, such as binding to different receptor binding sites on the insect.
[133] Plants or plant varieties (obtained by methods of plant biotechnology, such as genetic engineering) that can also be treated according to the invention are tolerant to abiotic stress factors. Such plants can be obtained by genetic transformation, or by selecting plants containing a mutation conferring resistance to such tension. Particularly, tolerant plants to useful tension include: a. plants containing a transgene capable of reducing the expression and / or activity of the poly (ADP-ribose) polymerase (PARP) gene in plant cells or plants; B. plants containing a transgene increasing the tolerance to tension capable of reducing the expression and / or activity of the genes encoding PARG of plants or plant cells; ç. plants containing a transgene increasing the tolerance to the strain encoding a functional plant enzyme from the nicotinamide adenine dinucleotide recovery biosynthesis pathway, including nicotinamidase, nicotinic acid mononucleotide adenyltransferase, nicotinamide amide adenyltransferase, nicotinamide amine additive.
[134] Plants or plant varieties (obtained by methods of plant biotechnology, such as genetic engineering) that can also be treated according to the invention show the altered quantity, altered quality and / or altered storage stability of the harvested product and / or altered properties of specific ingredients of the product harvested here, such as: 1) transgenic plants that synthesize a modified starch, in which their physico-chemical characteristics, in particular the amylose content or the amylose / amylopectin ratio, the degree of branching, the length of the medium chain, the distribution of the side chain, the viscosity behavior, the gel formation force, the size of the starch grains and / or the morphology of the starch grains, is altered in comparison with starch synthesized in plant cells or wild-type plants, so that this modified starch is more suitable for special applications; 2) transgenic plants that synthesize non-starch carbohydrate polymers or that synthesize non-starch carbohydrate polymers with altered properties compared to wild type plants without genetic modification; examples are plants that produce polyfructose, especially of the inulin type, levano and plants that produce alpha-1,4-glucans, plants that produce alpha-1,6-branched alpha-1,4-glucans, and plants that produce alternan; 3) transgenic plants that produce hyaluronic acid.
[135] The plants or varieties of plants (obtained by methods of plant biotechnology, such as genetic engineering) that can also be treated according to the invention are plants, such as cotton plants, with altered fiber characteristics. Such plants can be obtained by genetic transformation, or by selecting plants that contain a mutation conferring such altered fiber characteristics and include: a) plants, such as cotton plants, containing an altered form of cellulose synthase genes; b) plants, such as cotton plants, containing an altered form of homologous nucleic acids of rsw2 or rsw3; c) plants, such as cotton plants, with increased expression of sucrose phosphate synthase; d) plants, such as cotton plants, with increased expression of sucrose synthase; e) plants, such as cotton plants, in which the moment of plasmodesmatal switching at the base of the fiber cell is altered, for example, through the downward regulation of the selective β-1,3-glucanase fiber; f) plants, such as cotton plants, having fibers with altered reactivity, for example, through the expression of the N-acetylglucosaminetransferase gene including nodC, and the chitin synthase genes.
[136] The plants or varieties of plants (obtained by plant biotechnology methods, such as genetic engineering) that can also be treated according to the invention are plants, such as oilseed rape seed or related Brassica plants, with characteristics composition changes. Such plants can be obtained by genetic transformation, or by selecting plants containing a mutation conferring such altered oil characteristics and include: a) plants, such as rapeseed oilseed plants, which produce oil having a high oleic acid content; b) plants, such as oilseed rape plants, which produce oils having a low content of linolenic acid; c) plants, such as rapeseed oilseed plants, that produce oil having a low level of saturated fatty acids.
[137] Particularly useful transgenic plants that can be treated according to the invention are plants that comprise one or more genes that encode one or more toxins and the transgenic plants are available under the following trade names: YIELD GARD® (by corn, cotton, soybeans), KnockOut® (e.g. corn), BiteGard® (e.g. corn), BT-Xtra® (e.g. corn), StarLink® (e.g. corn), Bollgard ® (cotton), Nucotn® (cotton), Nucotn 33B® (cotton), NatureGard® (eg corn), Protecta® and NewLeaf® (potato). Examples of herbicide-tolerant plants that can be mentioned are maize varieties, cotton varieties and soy varieties that are available in the following trade names: Roundup Ready® (glyphosate tolerant, eg maize, cotton, soy), Liberty Link ® (tolerant to phosphinothricin, for example, oilseed rape), IMI® (tolerant to imidazolinones) and SCS® (tolerant to sulfonylurea, for example, corn). Herbicide resistant plants (plants grown in a conventional way for herbicide tolerance) that can be mentioned include cultivars sold under the name Clearfield® (for example, maize).
[138] Particularly useful transgenic plants that can be treated according to the invention are plants that contain transformation events, or a combination of transformation events, and that are listed, for example, in databases for various national or regional regulatory agencies (see, for example, http://gmoinfo.jrc.it/gmp_browse.aspx and http://www.agbios.com/dbase.php).
[139] The treatment according to the invention of plants and plant parts with combinations of active compounds is carried out directly or by allowing the compounds to act on their surrounding environment, environment or storage space by current treatment methods, for example , by immersion, spraying, evaporation, nebulization, spreading, apply on and, in the case of propagating material, in particular, in the case of seeds, also by applying one or more layers of coating.
[140] The mixtures according to the invention are particularly suitable for seed treatment. Here, a particular mention can be made of the combinations according to the aforementioned invention as preferred or particularly preferred. Thus, most damage to crop plants, which is caused by pests, occurs earlier, when the seed is infested during storage and then the seed is introduced into the soil, and during or immediately after plant germination. This phase is particularly critical since the roots and branches of the growing plant are particularly sensitive and even a small damage can lead to the death of the entire plant. The protection of the seed and the germinating plant through the use of appropriate compositions, therefore, is of great interest.
[141] Pest control by treating plant seeds has been known for a long time and is the subject of continuous improvement. However, seed treatment involves a number of problems that cannot always be satisfactorily solved. Thus, it is desirable to develop methods to protect the seed and the germinating plant that dispenses with the additional application of crop protection compositions after sowing or after the emergence of the plants. In addition, it is desirable to optimize the amount of active compound used in such a way as to provide optimum protection for the seed and the germinating plant from parasitic attack, but without damaging the plant itself by the active compound used. In particular, seed treatment methods must also take into account the intrinsic insecticidal properties of transgenic plants, in order to achieve optimum seed protection and also plant germination with a minimum of crop protection compositions to be employed .
[142] Therefore, the present invention, in particular, also relates to a method for the protection of germinating seeds and plants, from pest attacks, by treating the seed with a composition according to the invention. The invention also relates to the use of the compositions according to the invention for the treatment of seed to protect the seed and the resulting plant from pests. The invention also relates to seeds that have been treated with a composition according to the invention for protection from pests.
[143] One of the advantages of the present invention is that the particular systemic properties of the compositions according to the invention mean that treating the seed with these compositions not only protects the seed itself, but also the resulting plants after emergence, from of pests. Thus, immediate treatment of the crop at the time of sowing, or shortly thereafter, can be dispensed with.
[144] Another advantage is the increased synergistic insecticidal activity of the compositions according to the invention compared to the individual active insecticidal compound, which exceeds the expected activity of the two active compounds when applied individually. It is also advantageous to synergistically improve the fungicidal activity of the compositions according to the invention compared to the individual fungicidally active compound, which exceeds the expected activity of the individually applied active compound. This makes it possible to optimize the amount of active compounds used.
[145] Furthermore, it should be considered as advantageous that the mixtures according to the invention can also be used, in particular, in the transgenic seed, the plants resulting from the seed being able to express a protein directed against pests. When treating seeds with the compositions according to the invention, certain pests can be controlled simply by the expression of, for example, insecticidal protein and, in addition, damage to the seed can be avoided by the compositions according to the invention.
[146] The compositions according to the invention are suitable for the protection of seeds of any variety of plant, as already mentioned above, which is used in agriculture, greenhouse, forests or horticulture. In particular, it takes the form of maize, peanut, canola, oilseed rape, poppy, soybean, cotton, beet (eg sugar beet and fodder beet), rice, maize, wheat, barley, oats, rye , sunflower, tobacco, potatoes or vegetables (for example, tomatoes, cabbage species). The compositions according to the invention are also suitable for treating the seed of fruit and vegetable plants as already mentioned above. The treatment of corn, soy, cotton, wheat and canola or rapeseed seed is of particular importance.
[147] As already mentioned above, the treatment of transgenic seed with a composition according to the invention is also of particular importance. It takes the form of plant seeds which, as a general rule, comprise at least one heterologous gene that regulates the expression of a polypeptide, in particular, with insecticidal properties. In this context, the heterologous genes in the transgenic seed can be derived from microorganisms, such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium. The present invention is particularly suitable for the treatment of transgenic seed that comprises at least one heterologous gene from Bacillus sp. and whose gene product shows activity against the European corn borer and / or the corn rootworm. The gene involved is, more preferably, a heterologous gene that originates from Bacillus thuringiensis.
[148] Within the context of the present invention, the composition according to the invention is applied to the seed, either alone or in an appropriate formulation. Preferably, the seed is treated in a state where it is sufficiently stable to prevent damage during treatment. In general, the seed can be treated at any time between harvest and sowing. The seed, generally used, was separated from the plant and released from ears, husks, stems, coatings, hair or the flesh of the fruits.
[149] When treating the seed, it should generally be ensured that the amount of the composition according to the invention applied to the seed and / or the amount of other additives is selected in such a way that the germination of the seed is not impaired, or that the resulting plant is not damaged. This must be ensured in particular in the case of active compounds that can exhibit phytotoxic effects at certain rates of application.
[150] In addition, the compounds according to the invention can be used to control a multiplicity of different pests, including, for example, harmful sucking insects, biting insects and other pests that are plant parasites, stored material pests, pests that destroy industrial materials, and hygiene pests, including parasites in the animal health sector, and for its control, for example, its elimination and eradication. The present invention, therefore, also includes a method for pest control.
[151] In the animal health sector, that is, in the field of veterinary medicine, the active compounds according to the present invention act against parasites of animals, especially ectoparasites or endoparasites. The term "endoparasites" includes especially helminths, such as cestodes, nematodes or trematodes and protozoa, such as coccidia. Ectoparasites are typically and preferably arthropods, especially insects, such as flies (biting and licking), parasitic fly larvae, lice, hair lice, bird lice, fleas and the like; or mites, such as ticks, for example, hard or soft carcass ticks, or mites, such as scabies mites, harvest mites, bird mites and the like.
[152] These parasites include: of the order of Anoplurida, for example, Haematopinus spp., Linognathus spp., Pediculus spp., Phthirus spp. and Solenopotes spp .; specific examples are: Linognathus setosus, Linognathus vituli, Linognathus ovillus, Linognathus oviformis, Linognathus pedalis, Linognathus stenopsis, Haematopinus asini macrocephalus, Haematopinus eurysternus, Haematopinus suis, Pediculus humanus capis, Phenus of the order of Mallophagida and the suborders of Amblycerina and Ischnocerina, for example, Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp. and Felicola spp .; specific examples are: Bovicola bovis, Bovicola ovis, Bovicola limbata, Damalina bovis, Trichodectes canis, Felicola subrostratus, Bovicola caprae, Lepikentron ovis, Werneckiella equi; of the order of Diptera and the sub-orders Nematocerina and Brachycerina, for example, Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Odagmia spp., Wilhelmia spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp. ., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp. Melophagus spp., Rhinoestrus spp., Tipula spp .; specific examples are: Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles gambiae, Anopheles maculipennis, Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Fannia canicularis, Sarcophaga, Tipia sericata, Simulium reptans, Phlebotomus papatasi, Phlebotomus longipalpis, Odagmia ornata, Wilhelmia equina, Boophthora erythrocephala, Tabanus bromius, Tabanus spodopterus, Tabanus atratus, Tabanus sudeticus, Hybomitrausurichisopsis, chrysotaopsurea, Chrysota, citricus Musca domestica, Haematobia irritans irritans, Haematobia irritans exigua, Haematobia stimulans, Hydrotaea irritans, Hydrotaea albipuncta, Chrysomya cloropyga, Chrysomya bezziana, Oestrus ovis, Hypoderma bovis, Hypoderma lineatum, Przhevalskiana, Lipz, lipis, Henna, Lipis, lipis, Henna, Henna Hippobo sca variegata, Hippobosca equina, Gasterophilus intestinalis, Gasterophilus hemorrhoal, Gasterophilus inermis, Gasterophilus nasalis, Gasterophilus nigricornis, Gasterophilus pecorum, Braula coeca; from the order of Siphonapterida to, for example, Pulex spp., Ctenocephalides spp., Tunga spp., Xenopsylla spp., Ceratophyllus spp .; specific examples are: Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; from the order of Heteropterida, for example, Cimex spp., Triatoma spp., Rhodnius spp. and Panstrongylus spp; from the order of Blattarida, for example, Blatta orientalis, American Periplaneta, Blattela germanica and Supella spp. (for example, Suppella longipalpa); the subclass of Acari (Acarina) and the orders of meta- and Mesostigmata, for example, Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Dermanyssus spp., Rhipicephalus spp. (the original genus of ticks with multiple hosts), Ornithonyssus spp., Pneumonyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp., Acarapis spp .; specific examples are: Argas persicus, Argas reflexus, Ornithodorus moubata, Otobius megnini, Rhipicephalus (Boophilus) microplus, Rhipicephalus (Boophilus) decoloratus, Rhipicephalus (Boophilus) annulatus, Rhipicephalus (Boophilus) Hyacatomomomomum, Hyalomalomalum, Hyalomalum, Hyalomalomum, Hyalomalom transiens, Rhipicephalus evertsi, Ixodes ricinus, Ixodes hexagonus, Ixodes canisuga, Ixodes pilosus, Ixodes rubicundus, Ixodes scapularis, Ixodes holocyclus, Haemaphysalis concinna, Haemaphysalis punctata, Haemaphysisisisisisisisisisisisysisisismaysalis, haisphysisisis Dermacentor pictus, Dermacentor albipictus, Dermacentor andersoni, Dermacentor variabilis, Hyalomma mauritanicum, Rhipicephalus sanguineus, Rhipicephalus bursa, Rhipicephalus appendiculatus, Rhipicephalus capensis, Rhipicepmaus ambisomomis, Ambient mum, Rothicephalus turanicus, Ambient mum latum, Amblyomma hebraeum, Amblyomma cajennense, Dermanyssus gallinae, Ornithonyssus bursa, Ornithonyssus sylviarum, Varroa jacobsoni; of the order of Actinedida (Prostigmata) and Acaridida (Astigmata), for example, Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp. ., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Cytodites spp. specific examples are: Cheyletiella yasguri, Cheyletiella blakei, Demodex canis, Demodex bovis, Demodex ovis, Demodex caprae, Demodex equi, Demodex caballi, Demodex suis, Neotrombicula autumnalis, Neotrombicula desaleri, Neoschongastia, Tumeric, Mastic canis, Sarcoptes bovis, Sarcoptes ovis, Sarcoptes rupicaprae (= S. caprae), Sarcoptes equi, Sarcoptes suis, Psoroptes ovis, Psoroptes cuniculi, Psoroptes equi, Chorioptes bovis, Psoergates ovis, Pneumonyssoidic mange, Pneumonisisisis mane, Pneumon
[153] The active compounds according to the invention are also suitable for the control of arthropods, helminths and protozoa that attack animals. Animals include agricultural livestock, for example, cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, captive fish, bees. Animals also include pets - also known as pets - for example, dogs, cats, cage birds, aquarium fish, and which are known as test animals, for example, hamsters, guinea pigs, rats and mice .
[154] The control of these arthropods, helminths and / or protozoa should reduce cases of death and improve the yield (for meat, milk, wool, skins, eggs, honey, etc.) and the health of the host animal, and so the Use of the active compounds according to the invention allows livestock to be more economically viable and easier.
[155] For example, it is desirable to prevent or interrupt the host's blood absorption by parasites (if relevant). Parasite control can also contribute to the prevention of the transmission of infectious substances.
[156] The term "control", as used herein, with respect to the field of animal health means that the active compounds act by reducing the occurrence of the parasite in question, in an animal infested with these parasites to a harmless level. More specifically, "control", as used herein, means that the active compound kills the parasite in question, slows its growth or inhibits its proliferation.
[157] In general, the active compounds according to the invention can be used directly, when they are used for the treatment of animals. They are preferably used in the form of pharmaceutical compositions which can comprise pharmaceutically acceptable excipients and / or adjuvants known in the art.
[158] In the animal health and livestock sector, the active compounds are used (administered) in a known way, by enteral administration in the form of, for example, tablets, capsules, potions, liquid medicines, granules, pastes, boluses, process through food and suppositories, by parenteral administration, for example, by injection (intramuscular, subcutaneous, intravenous, intraperitoneal among others), implants, by nasal administration, through dermal administration, in the form, for example, of immersion or bathing, spraying, pouring over and staining over, washing and powdering powder, and also with the aid of molded articles containing the active compound, such as collars, identification marks on the animals ear, identification marks on the tail of animals, bandages of limbs, halters, marking devices, etc. The active compounds can be formulated in the form of a shampoo or as suitable formulations applicable in aerosols or non-pressurized sprayers, for example, pump sprayers and atomizing sprayers.
[159] In the case of use for livestock, poultry, domestic animals, etc., the active compounds according to the invention can be used as formulations (for example, powders, wet powders ["WP"], emulsions, concentrates emulsifiable ["CE"], free-flow compositions, homogeneous solutions and suspension concentrates ["SC"]), which contain the active compounds in an amount of 1 to 80% by weight, directly or after dilution (for example, dilutions of 100 to 10000 times), or they can be used as a chemical bath.
[160] In the case of use in the animal health sector, the active compounds according to the invention can be used in combination with suitable synergistic agents or other active compounds, for example, insecticides, acaricides, anthelmintics, anthelmintics protozoa.
[161] The compounds according to the invention can be prepared by usual methods known to those skilled in the art.
[162] Reaction Scheme 1 illustrates general process A for the preparation of the compounds (I-1) according to the invention. Reaction Scheme 1

[163] The radicals A1-A4, Q, W, R1 and Z1-Z2 3 * 5 have the meaning described above. The five-membered cycles of E1-E3, carbon and nitrogen represent the 5-membered heterocycles defined under T. X represents a halogen. U represents bromine, iodine or triflate, if M represents boronic acid, boronic ester or trifluoroboronate. U represents boronic acid, boronic ester or trifluoroboronate if M represents bromine, iodine or triflate.
[164] The compounds according to the invention of general structure (I-1) can be prepared by processes known from the literature using palladium catalyzed reactions of reaction partners 4 and 5 [WO2005-040110; WO2009-089508]. Compounds of general structure 5 are either commercially available or can be prepared by processes known to those skilled in the art. Compounds of general structure 4 can be prepared by processes known from the literature or by nucleophilic substitution on the aromatic ring (X = chlorine or fluorine) [WO2007-107470; Tetrahedron Letters 2003, 44, 7629-7632], or by a reaction catalyzed by a transition metal (X = bromine or iodine) [WO2012-003405; WO2009-158371] from the appropriate starting materials, 2 and 3.
[165] Alternatively, the compounds (Ia) according to the invention can be prepared by the general preparation process B (Reaction Scheme 2). Reaction Scheme 2

[166] The radicals A1-A4, Q, R1 and Z1-Z3 have the meanings described above. The five-membered cycles of E1-E3, carbon and nitrogen represent the 5-membered heterocycles defined under T. U represents bromine, iodine or triflate, if M represents a boronic acid, boronic ester or trifluoroboronate. U represents boronic acid, boronic ester or trifluoroboronate if M represents bromine, iodine or triflate.
[167] The compounds according to the invention of the general structure (I-1) can be prepared in a manner analogous to the known methods of peptide coupling of the literature from starting materials 8 and 9 [WO2010-05196; WO2010-133312]. Compounds of general structure 8 can be prepared in a manner analogous to processes known in the literature by cleavage of esters from compounds of general structure 7 [WO2010-051926; WO2010-133312]. Compounds of general structure 7 can be prepared in a manner analogous to the processes known from the literature through the reactions catalyzed by palladium [WO2005-040110; WO2009-089508].
[168] The compounds according to the invention of general structure (I-2) can be synthesized by the process of preparation C shown in Reaction Scheme 3.

[169] The radicals A1-A4, Q, R1 and Z1-Z3 have the meanings described above. The five-membered cycles of E1-E3, carbon and nitrogen represent the 5-membered heterocycles defined under T.
[170] The compounds according to the invention of the general structure (I-2) can be prepared analogously to processes known in the literature from compounds of general structure (I-1) [WO2012-056372; WO2003- 066050].
[171] The compounds according to the invention of the general structure (I-1a) can be synthesized by the preparation process D shown in Reaction Scheme 4. Reaction Scheme 4

[172] The radicals A1-A4, Q, W, R1, Z1 and Z3 have the meanings described above. Z2 represents radicals, such as fluorine, chlorine, bromine, iodine, cyano, methylsulfanyl, hydroxy and other radicals that can from the 4b diazonium salt [Chemical Reviews 1988, E1-E3, carbon and nitrogen five-member cycles represent the 5-membered heterocycles defined under T. X represents a halogen. U represents bromine, iodine or triflate and M represents boronic acid, boronic ester or trifluoroboronate.
[173] The compounds according to the invention of the general structure (I-1a) can be prepared by processes known from the literature using palladium catalyzed reactions of reaction partners 4c and 5 [WO2005-040110; WO2009-089508]. Compounds of general structure 5 are either commercially available or can be prepared by processes known to those skilled in the art. Compounds of general structure 4c can be prepared by processes known from the literature from compounds of general structure 4b [Chemical Reviews 1988, 88, 5, 765-792]. Compounds of general structure 4b can be prepared from compounds of general structure 4a by processes known from the literature [WO2008-008375; Journal of Heterocyclic Chemistry 2002, 39 (5), 1055-1059]. Compounds of general structure 4a can be prepared by processes known from the literature or by nucleophilic substitution on the aromatic ring (X = chlorine or fluorine) [WO2007-107470; Tetrahedron Letters 2003, 44, 7629-7632], or by a reaction catalyzed by a transition metal (X = bromine or iodine) [WO2012-003405; WO2009- 158371] from the appropriate starting materials 2a and 3.
[174] Compounds of general structure 5 are either commercially available or can be prepared by processes known to those skilled in the art or analogously to these processes [WO2012004217; WO2009-130475; WO2008-1012125; WO2003-099805; WO2012-0225061; WO2009-010488].
[175] Compounds of general structure 2 / 2a are either commercially available or can be prepared by processes known to those skilled in the art or analogously to these processes [WO2010-051926; WO2011-131615; WO2006-018725; WO2012-065932; WO2007077961; US2012-0115903; WO2010-017902; WO2010-127856; Tetrahedron Letters 2011, 44, 8451-8457].
[176] Compounds of general structure 3 are commercially available or can be prepared by processes known to those skilled in the art or analogously to those processes.
[177] Oxidizing agents for the oxidation of alcoholic groups are known (as, for example, oxidizing agents in Organic Synthesis by Oxidation with Metal Compounds, Mijs, de Jonge, Plenum Verlag, New York, 1986; Manganese Compounds as Oxidizing Agents in Organic Chemistry, Arndt, Open Court Publishing Company, La Salle, IL, 1981; The Oxidation of Organic Compounds by Permanganate Ion and Hexavalent Chromium, Lee, Open Court Publishing Company, La Salle, IL, 1980). An oxidation can be carried out, for example, in the presence of permanganates (eg, potassium permanganate), metal oxides (eg, manganese dioxide, chromium oxides, which are used, for example, in dipyridinachrome oxide ( VI) as Collins' reagent (according to, JC Collins et al., Tetrahedron Lett. 30, 3363-3366, 1968)). Likewise, in the presence of pyridinium chlorochromate (for example, Corey's reagent) (as also RO Hutchins et al., Tetrahedron Lett 48, 4167-4170, 1977; D. Landini et al. Synthesis 134-136, 1979), or ruthenium tetroxide (according to S.-I. Murahashi, N. Komiya Ruthenium-catalyzed Oxidation of Alkenes, Alcohols, Amines, Amides, β-Lactams, Phenols and Hydrocarbons, in: Modern Oxidation Methods, Baeckvall, Jan -Erling (Eds.), Wiley-VCH-Verlag GmbH & Co. KGaA, 2004). Equally suitable are ultrasound-induced oxidation reactions and the use of potassium permanganate (according to J. Yamawaki et al., Chem. Lett. 3, 379- 380, 1983).
[178] All known auxiliaries for the appropriate acid or basic reaction can be used according to the procedures described in the literature to unlock / remove the SG protection group. When carbamate-type protecting groups are used for amino groups, preference is given to the use of acidic reaction aids. When the protecting group t-butylcarbamate (BOC group) is used, for example, mixtures of mineral acids, such as hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid, phosphoric acid or organic acids, such as benzoic acid, formic acid , acetic acid, trifluoroacetic acid, methanesulfonic acid, benzenesulfonic acid or toluenesulfonic acid and a suitable diluent, such as water and / or an organic solvent such as tetrahydrofuran, dioxane, dichloromethane, chloroform, ethyl acetate, ethanol or methanol used. Preference is given to mixtures of hydrochloric acid or acetic acid with water and / or an organic solvent, such as ethyl acetate.
[179] It is known that certain reactions and preparation processes can be carried out with special efficiency in the presence of diluents or solvents and acid or basic reaction aids. It is also possible to use mixtures of the diluents or solvents. The diluents or solvents are advantageously used in such an amount that the reaction mixture remains easily agitated throughout the process.
[180] The appropriate diluents or solvents for carrying out the processes according to the invention are, in principle, all organic solvents that are inert under the specific reaction conditions. Examples include: halogenated halohydrocarbons (for example, chlorinated hydrocarbons, such as tetrachlorethylene, tetrachloroethane, dichloropropane, methylene chloride, dichlorobutane, chloroform, carbon tetrachloride, trichloroethane, trichlorethylene, pentachloroethane, dichlorobenzene, 1,2 dichlorobenzene, chlorotoluene, trichlorobenzene), alcohols (for example, methanol, ethanol, isopropanol, butanol), ethers (for example, ethyl propyl ether, tert-butyl methyl ether, n-butyl ether, anisol, phenethol, cyclohexyl methyl ether, ether dimethyl, diethyl ether, dipropyl ether, diisopropyl ether, di-n-butyl ether, diisopropyl ether, diisopropyl ether, ethylene glycol dimethyl ether, tetrahydrofuran, dioxane, dichlorodiethyl ether and polyether oxides. ethylene and / or propylene oxide), amines (eg trimethyl-, triethyl-, tripropyl-, tributylamine, N-methylmorpholine, pyridine and tetramethylenediamine), nitrohydrocarbons ( for example, nitromethane, nitroethane, nitropropane, nitrobenzene, chloronitrobenzene, o-nitrotoluene); nitriles (eg, acetonitrile, propionitrile, butyronitrile, isobutyronitrile, benzonitrile, m-chlorobenzonitrile), tetrahydrothiophene dioxide, dimethyl sulfoxide, tetramethylene sulfoxide, dipropyl sulfoxide, methyl benzyl sulfoxide, diisobutyl sulfoxide, dibutyl, diisopropyl sulfoxide, sulfones (e.g. dimethyl, diethyl, dipropyl, dibutyl, diphenyl, dihexyl, methyl ethyl, ethyl propyl, ethyl isobutyl and pentamethylene), aliphatic, cycloaliphatic or aromatic hydrocarbons (for example, pentane, hexane, heptane, octane, nonane and technical hydrocarbons), and also that they are called "white essence" with components having boiling points in the range of, for example, 40 ° C to 250 ° C, cymene, oil fractions within the boiling range of 70 ° C to 190 ° C, cyclohexane, methylcyclohexane, petroleum ether, ligroin, octane, benzene, toluene, chlorobenzene, bromobenzene, nitrobenzene, xylene, esters (eg methyl carbonate, ethyl l, butyl and isobutyl acetate, dimethyl, dibutyl and ethylene); amides (for example, hexamethylphosphoric triamide, formamide, N-methylformamide, N, N-dimethylformamide, N, N-dipropylformamide, N, N-dibutylformamide, N-methylpyrrolidine, N-methylcaprolactam, 1,3-dimethyl-3,4, 5,6-tetrahydro-2 (1H) -pyrimidine, octylpyrrolidone, octylcaprolactam, 1,3-dimethyl-2-imidazolinedione, N-formylpiperidine, N, N'-diformylpiperazine) and ketones (eg acetone, acetophenone, methyl ethyl ketone, butyl methyl ketone).
[181] The basic reaction aids used to carry out the process according to the invention can be all suitable acid binding agents. Examples include: alkaline earth metal compounds or alkali metal compounds (eg hydroxides, hydrides, lithium, sodium, potassium, magnesium, calcium and barium hydroxides and carbonates), amidine bases or guanidine bases (eg 7 -methyl-1,5,7- triazabicyclo [4.4.0] dec-5-ene (MTBD); diazabicyclo [4.3.0] nonene (DBN), diazabicyclo [2.2.2] octane (DABCO), 1,8- diazabicyclo [5.4.0] undecene (DBU), cyclohexyl-tetrabutylguanidine (CyTBG), cyclohexyl-tetramethylguanidine (CyTMG), N, N, N, N-tetramethyl-1,8-naphthalenediamine, pentamethylpiperidine) and amines, especially tertiary amines (for example, triethylamine, trimethylamine, tribenzylamine, triisopropylamine, tributylamine, tricyclohexylamine, triamylamine, trihexylamine, N, N-dimethylaniline, N, N-dimethylololidine, N, N-dimethyl-p-aminopyridine, N-methylpyrrolid, N-methylpiperidine, N-methylimidazole, N-methylpyrazole, N-methylmorpholine, N-methylhexamethylenediamine, pyridine, 4-pyrrolidinopyridine, 4-dimethylaminopyridine a, quinoline, α-picoline, β-picoline, isoquinoline, pyrimidine, acridine, N, N, N ', N'- tetramethylenediamine, N, N, N', N'-tetraethylenediamine, quinoxaline, N-propyldiisopropylamine, N-ethyldiisopropylamine, N, N'-dimethylcyclohexylamine, 2,6-lutidine, 2,4-lutidine or triethyldiamine).
[182] The acidic reaction aids used to carry out the process according to the invention include all mineral acids (for example, hydrohalic acids, such as hydrofluoric acid, hydrochloric acid, hydrobromic acid or hydroiodic acid, and also sulfuric acid, phosphoric acid, phosphorous acid, nitric acid), Lewis acids (for example, aluminum (III) chloride, boron trifluoride or its etherate, titanium (IV) chloride, tin (IV) chloride) and organic acids ( for example, formic acid, acetic acid, propionic acid, malonic acid, lactic acid, oxalic acid, fumaric acid, adipic acid, stearic acid, tartaric acid, oleic acid, methanesulfonic acid, benzoic acid, benzenesulfonic acid or para-toluenesulfonic acid) .
[183] If protection groups are intended for reaction schemes, all generally known protection groups can be used. In particular, those described by Greene T.W., Wuts P. G. W. in Protective Groups in Organic Synthesis; John Wiley & Sons, Inc. 1999, "Protection for the hydroxyl group including 1,2- and 1,3-diols".
[184] Protection groups are also suitable: substituted methyl ether type (for example, methoxymethyl ether (MOM), methylthiomethyl ether (MTM), (phenyldimethylsilyl) methoxymethyl ether (SNOM-OR), benzyloxymethyl ether (BOM-OR) para-methoxybenzyloxymethyl ether (PMBM-OR), para-nitrobenzyloxymethyl ether, ortho-nitrobenzyloxymethyl ether (NBOM-OR), (4-methoxyphenoxy) methyl ether (p-AOM-OR), guaiacolmethyl ether (GUM-OR), t- butoxymethyl ether, 4-pentyloxymethyl ether (POM-OR), silyloxymethyl ether, 2-methoxyethoxymethyl ether (MEM-OR), 2,2,2-trichloroethoxymethyl ether, bis (2-chloroethoxy) methyl ether, 2- (trimethylsilyl) ethoxymethyl ether (SEM-OR), methoxymethyl ether (MM -OR)); substituted ethyl ether type (for example, 1- ethoxyethyl ether (EE-OR), 1- (2-chloroethoxy) ethyl ether (EEC-OR), 1- [2- (trimethylsilyl) ethoxy] ethyl ether (SEE-OR ), 1-methyl-1-methoxyethyl ether (MIP-OR), 1-methyl-1-benzylxyethyl ether (MBE-OR), 1-methyl-1-benzyloxy-2-fluoroethyl ether (MIP-OR), 1- methyl-1-phenoxyethyl ether, 2,2,2-trichloroethyl ether, 1,1-dianisyl-2,2,2-trichloroethyl ether (DATE-OR), 1,1,1,3,3,3-hexafluoro- 2-phenylisopropyl ether (HIP-OR), 2-trimethylsilylethyl ether, 2- (benzylthio) ethyl ether, 2- (phenylselenyl) ethyl ether), an ether (for example, tetrahydropyranyl ether (THP-OR), 3- bromotetrahydropyranyl ether (3-BrTHP-OR), tetrahydrothiopyranyl ether, 1-methoxycyclohexyl ether, 2- and 4-picolyl ether, 3-methyl-2-picolyl-N-oxide ether, 2-quinolinylmethyl ether ( Qm-OR), 1-pyrenylmethyl ether, diphenylmethyl ether (DPM-OR), para, para'-dinitrobenzohydryl ether (DNB-OR), 5-dibenzosuberyl ether, triphenylmethyl ether (Tr-OR), alpha-naphthylphenylmethyl ether, para - methoxyphenyldiphenylmethyl ether (MMTrOR), di (para-methoxyphenyl ) phenylmethyl ether (DMTr-OR), tri (para-methoxyphenyl) phenylmethyl ether (TMTr-OR), 4- (4'-bromophenacyloxy) phenyldiphenylmethyl ether, 4.4 ', 4' '- tris (4,5-dichlorophthalimidophenyl) ) methyl ether (CPTr-OR), 4.4 ', 4' '- tris (benzoyloxyphenyl) methyl ether (TBTr-OR), 4,4'-dimethoxy-3' '- [N- (imidazolylmethyl)] trityl ether (IDTr-OR), 4,4'-dimethoxy-3 '' - [N- (imidazolylethyl) carbamoyl] trityl ether (IETr-OR), 1,1-bis (4-methoxyphenyl) -1'-pyrenylmethyl ether ( Bmpm-OR), 9-anthryl ether, 9- (9-phenyl) xanthenyl ether (Pixyl-OR), 9- (9-phenyl-10-oxo) antril (tritylone ether), 4-methoxytetrahydropyranyl ether (MTHP -OR), 4-methoxytetrahydrothiopyranyl ether, 4-methoxytetrahydrothiopyranyl S, S-dioxide, 1- [(2-chloro-4-methyl) phenyl] -4-methoxypiperidin-4-yl ether (CTMP-OR) , 1- (2-fluorophenyl) -4-methoxypiperidin-4-yl ether (Fpmp-OR), 1,4-dioxan-2-yl ether, tetrahydrofuranyl ether, tetrahydrothiofuranyl ether, 2,3,3a, 4,5,6,7,7a-octahydro-7,8,8-trimethyl-4,7-methanobenzofuran-2-yl ether (MBF-OR), t-butyl ether, allyl ether, propargyl ether, for - chlorophenyl ether of, para-methoxyphenyl ether, para-nitrophenyl ether, para-2,4-dinitrophenyl ether (DNP-OR), 2,3,5,6-tetrafluoro-4- (trifluoromethyl) phenyl ether, benzyl ether (Bn-OR )); substituted benzyl ether (for example, para-methoxybenzyl ether (MPM-OR), 3,4-dimethoxybenzyl ether (DMPM-OR), ortho-nitrobenzyl ether, para-nitrobenzyl ether, para-halobenzyl ether, 2.6 -dichlorobenzyl ether, para-aminoacylbenzyl ether (PAB-OR), para-azidobenzyl ether (AZB-OR), 4-azido-3-chlorobenzyl ether, 2-trifluoromethylbenzyl ether, para- (methylsulfinyl) benzyl ether (MSIB-OR) ); of the silyl ether type (for example, trimethylsilyl ether (TMS-OR), triethylsilyl ether (TES-OR), triisopropylsilyl ether (TIPS-OR), dimethylisopropylsilyl ether (IPDMS-OR), diethylisopropylsilyl ether (DEIPS-OR), dimethylhexylsilyl ether (TDS-OR), t-butyldimethylsilyl ether (TBDMS-OR), t-butyldiphenylsilyl ether (TBDPS-OR), tribenzylsilyl ether, tri-para-xylylsilyl ether, triphenylsilyl ether (TPS-OR), diphenylmethyl -OR), di-t-butylmethylsilyl ether (DTBMS-OR), tris (trimethylsilyl) silyl ether (sisil ether), di-t-butylmethylsilyl ether (DTBMS-OR), tris (trimethylsilyl) silyl ether (sisil ether), (2-hydroxystyryl) dimethylsilyl ether (HSDMS-OR), (2-hydroxystyryl) diisopropylsilyl ether (HSDIS-OR), t-butylmethoxyphenylsilyl ether (TBMPS-OR), t-butoxydiphenylsilyl ether (DPTBOS-OR); ester type (for example, formate ester, benzoylformate ester, acetate ester (Ac-OR), chloroacetate ester, dichloroacetate ester, trichloroacetate ester, trifluoroacetate ester, (TFA-OR), methoxyacetate ester, triphenylmethoxyacetate ester, phenoxyacetate ester, para-chlorophenoxyacetate ester, phenylacetate ester, diphenylacetate ester (DPA-OR), nicotinate ester, 3-phenylpropionate ester, 4-pentoate ester, 4-oxopateate ester ) (Lev-OR), 4,4- (ethylenedithio) pentanoate ester (levS-OR), 5- [3-bis (4-methoxyphenyl) hydroxymethoxyphenoxy] levulinate ester, pivaloate ester (PV-OR), ester 1-adamantanoate, crotonate ester, 4-methoxychrotonate ester, benzoate ester (Bz-OR), para-phenylbenzoate ester, 2,4,6-trimethylbenzoate ester (mesitoate), 4- (methylthiomethoxy) ester butyrate (MTMB-OR), 2- (methylthiomethoxymethyl) benzoate ester (MTMT-OR); ester type (eg methyl carbonate, methoxymethyl carbonate, carbonate 9-fluorenylmethyl (Fmoc-OR), ethyl carbonate, 2,2,2-trichloroethyl carbonate (Troc-OR), 1,1-dimethyl-2,2,2-trichloroethyl carbonate (TCBOC-OR), 2- (trimethylsilyl) ethyl carbonate (TMS-OR), 2- (phenylsulfonyl) ethyl carbonate (Ps-OR), 2- (triphenylphosphonium) ethyl carbonate (Peoc-OR), t-butyl carbonate (Boc- OR), isobutyl carbonate, vinyl carbonate, allyl carbonate (Alloc-OR), para-nitrophenyl carbonate, benzyl carbonate (Z-OR), para-methoxybenzyl carbonate, 3,4-dimethoxybenzyl carbonate, carbonate ortho-nitrobenzyl, para-nitrobenzyl carbonate, 2-dansylethyl carbonate (Dnseoc-OR), 2- (4-nitrophenyl) ethyl carbonate (Npeoc-OR), 2- (2,4-dinitrophenyl) ethyl carbonate (Dnpeoc)), and of the sulfate type (for example allylsulfonate (ALS-OR), methanesulfonate (Ms-OR), benzylsulfonate, tosylate (Ts-OR), 2- [(4-nitrophenyl) ethyl] sulfonate (Npes-OR )).
[185] The catalysts suitable for carrying out a catalytic hydrogenation in the process according to the invention are all the usual hydrogenation catalysts, such as, for example, platinum catalysts (eg platinum plate, platinum sponge, black platinum, colloidal platinum, platinum oxide, platinum wire), palladium catalysts (e.g. palladium sponge, palladium black, palladium oxide, palladium / carbon support, colloidal palladium, palladium / barium sulfate support , palladium / barium carbonate support, palladium hydroxide, nickel catalysts (eg reduced nickel, nickel oxide, Raney nickel), ruthenium catalysts, cobalt catalysts (eg reduced cobalt, Raney cobalt ), copper catalysts (eg reduced copper, Raney copper, Ullmann copper). Preference is given to the use of noble metal catalysts (eg palladium or platinum and ruthenium catalysts), which They can be applied to a suitable support (for example, carbon or silicon), rhodium catalysts (for example, tris (triphenylphosphine) rhodium (I) chloride in the presence of triphenylphosphine). In addition, it is possible to use "chiral hydrogenation catalysts" (for example, those comprising chiral diphosphine binders, such as (2S, 3S) - (-) - 2,3-bis (diphenylphosphino) butane [(S, S) - quirafos] or (R) - (+) - 2,2'- or (S) - (-) - 2,2'- bis (diphenylphosphino) -1,1'-binaphthalene [R (+) - BINAP or S (-) - BINAP]), in which the proportion of one isomer in the mixture of isomers is increased or the formation of another isomer is virtually completely suppressed.
[186] The salts of the compounds according to the invention are prepared by conventional methods. Representative acid addition salts are, for example, those formed by reaction with inorganic acids, such as, for example, sulfuric acid, hydrochloric acid, hydrobromic acid, phosphoric acid, or organic carboxylic acids, such as acetic acid, trifluoroacetic acid , citric acid, succinic acid, butyric acid, lactic acid, formic acid, fumaric acid, maleic acid, malonic acid, camphoric acid, oxalic acid, phthalic acid, propionic acid, glycolic acid, glutaric acid, stearic acid, salicylic acid, sorbic, tartaric acid, cinnamic acid, valeric acid, picric acid, benzoic acid or organic sulfonic acids, such as methanesulfonic acid and 4-toluenesulfonic acid.
[187] Also representative are salts of compounds according to the invention formed from organic bases, such as, for example, pyridine or triethylamine, or those that are formed from inorganic bases, such as, for example, hydrides, hydroxides or carbonates of sodium, lithium, calcium, magnesium or barium, provided that the compounds of general formula (I) have a structural element suitable for this salt formation.
[188] Synthetic methods for the preparation of heterocyclic N-oxides and t-amines are known. They can be obtained using peroxy acids (for example, peracetic acid and meta-chloroperbenzoic acid (MCPBA), hydrogen peroxide), alkyl hydroperoxides (for example, t-butyl hydroperoxide), sodium perborate and dioxiranes (for example, dimethyldioxirane ). These methods have been described, for example, by TL Gilchrist, in Comprehensive Organic Synthesis, Vol. 7, pp. 748-750, 1992, SV Ley, (Ed.), Pergamon Press; M. Tisler, B. Stanovnik, in Comprehensive Heterocyclic Chemistry, Vol. 3, pp. 18-20, 1984, AJ Boulton, A. McKillop, (Eds.), Pergamon Press; MR Grimmett, BRT Keene in Advances in Heterocyclic Chemistry, Vol. 43, pp. 149-163, 1988, AR Katritzky, (Ed.), Academic Press; M. Tisler, B. Stanovnik, in Advances in Heterocyclic Chemistry, Vol. 9, pp. 285-291, 1968, AR Katritzky, AJ Boulton (Eds.), Academic Press; GWH Cheeseman, ESG Werstiuk in Advances in Heterocyclic Chemistry, Vol. 22, pp. 390-392, 1978, AR Katritzky, AJ Boulton, (Eds.), Academic Press. Experimental part Preparation Process Example (Ic-1) 2-Chloro-N-cyclopropyl-5- [2'-methyl-5'- (pentafluoroethyl) -4 '- (trifluoromethyl) -2'H-1,3' -bipyrazol-4-yl] benzamide

[189] 2.00 g (6.99 mmol) of 5-fluoro-1-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazole, 1.03 g (6.99 mmol) of 4 -bromo-1H-pyrazole and 1.93 g of potassium carbonate are suspended in 50 ml of tetrahydrofuran for the reaction mixture is heated under reflux for 16 h. The cooled reaction mixture is filtered and the solvent is removed under reduced pressure. The residue is purified by silica gel column chromatography.
[190] This provides 0.69 g of 4-bromo-2'-methyl-5'- (pentafluoroethyl) -4 '- (trifluoromethyl) -2'H-1,3'-bipyrazole as a colorless solid.
[191] 1H-NMR (400 MHz, d3-acetonitrile): δ = 8.00 (s, 1H), 7.91 (s, 1H), 3.71 (s, 3H).
[192] HPLC-MSa): logP = 4.14 mass spectrum (m / z) = 413 [M + H] +.
[193] 10.5 mL of isopropyl alcohol is added to 150 mg (0.36 mmol) of 4-bromo-2'-methyl-5'- (pentafluoroethyl) -4 '- (trifluoromethyl) -2'H-1 , 3'-bipyrazole, 87 mg (0.36 mmol) of [4-chloro-3- (cyclopropylcarbamoyl) phenyl] boronic acid, 21 mg (0.01 mmol) of tetrakis (triphenylphosphine) palladium and 1.1 ml of a 1M aqueous solution of sodium bicarbonate, and the mixture is heated under reflux for 3 h. The reaction mixture is concentrated until dry and the residue is taken up in ethyl acetate. The organic phase is washed twice with water, dried over sodium sulfate, filtered and concentrated until dry. The crude product is purified by silica gel column chromatography.
[194] This provides 71 mg of 2-chloro-N-cyclopropyl- 5- [2'-methyl-5 '- (pentafluoroethyl) -4' - (trifluoromethyl) -2'H- 1,3'-bipyrazole-4 -yl] benzamide as a colorless solid.
[195] 1H-NMR (400 MHz, d3-acetonitrile): δ = 8.26 (s, 1H), 8.24 (s, 1H), 7.67 (d, 1H), 7.65 (dd, 1H), 7.48 (d, 1H), 6.95 (s, 1H), 3.75 (s, 3H), 2.82-2.87 (m, 1H), 0.75-0.80 (m, 2H). 0.57-0.62 (m, 2H).
[196] HPLC-MSa): logP = 3.79 mass spectrum (m / z) = 528 [M + H] +. Preparation Process B Example (Ib1) N-Benzyl-2-chloro-5- {1- [1-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl] -1H-imidazole -4-yl} benzamide

[197] 500 mg (1.74 mmol) of 5-fluoro-1-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazole, 339 mg (1.74 mmol) of 4-iodine-1H -imidazole and 483 mg (3.49 mmoles) of potassium carbonate are suspended in 20 ml of tetrahydrofuran for the reaction mixture is heated under reflux until the reaction is complete. The cooled reaction mixture is filtered and the solvent is removed under reduced pressure. The residue is purified by silica gel column chromatography.
[198] This provides 370 mg of 5- (4-iodo-1H-imidazol-1-yl) -1-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazole as a colorless solid.
[199] 1H-NMR (400 MHz, d3-acetonitrile): δ = 7.68 (d, 1H), 7.43 (d, 1H), 3.68 (s, 3H) ppm.
[200] HPLC-MSa): logP = 3.47 mass spectrum (m / z) = 461 [M + H] +.
[201] 20 ml of isopropyl alcohol is added to 250 mg (0.54 mmol) of 5- (4-iodo-1H-imidazol-1-yl) -1- methyl-3- (pentafluoroethyl) -4- ( trifluoromethyl) -1H-pyrazole, 161 mg (0.54 mmol) of 2-chloro-5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) methyl benzoate, 31 mg (0.02 mmol) of tetrakis (triphenylphosphine) palladium and 1.66 ml of a 1M aqueous solution of sodium bicarbonate, and the mixture is heated under reflux for 3 h. The reaction mixture is concentrated until dry and the residue is taken up in ethyl acetate. The organic phase is washed twice with water, dried over sodium sulfate, filtered and concentrated until dry. The crude product is purified by silica gel column chromatography.
[202] This provides 160 mg of 2-chloro-5- {1- [1- methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl] -1H-imidazol-4-yl } methyl benzoate as a colorless solid.
[203] 1H-NMR (400 MHz, d3-acetonitrile): δ = 8.28 (d, 1H), 7.95 (dd, 1H), 7.83 (d, 1H), 7.71 (d, 1H), 7.55 (d, 1H), 3.91 (s, 3H), 3.73 (s, 3H) ppm.
[204] HPLC-MSa): logP = 4.26, mass spectrum (m / z) = 503 [M + H] +.
[205] 150 mg (0.29 mmol) of 2-chloro-5- {1- [1-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl] -1H-imidazole -4-yl} methyl benzoate are dissolved in 6.3 ml of tetrahydrofuran pa, and the mixture is cooled with ice. 8.54 mg of lithium hydroxide, dissolved in 0.7 ml of water, are added dropwise to the reaction solution. After 10 minutes, the ice-cooling is removed and the reaction mixture is stirred at room temperature for an additional 18 h. The reaction mixture is acidified with 1M hydrochloric acid and the product is extracted with ethyl acetate. The organic phase is washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure.
[206] This provides 127 mg of 2-chloro-5- {1- [1-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl] -1H-imidazole-4 acid -il} benzoic as a colorless solid.
[207] 1H-NMR (400 MHz, d3-acetonitrile): δ = 8.31 (d, 1H), 7.96 (dd, 1H), 7.83 (d, 1H), 7.72 (d, 1H), 7.55 (d, 1H), 3.73 (s, 3H) ppm.
[208] HPLC-MSa): logP = 3.30, mass spectrum (m / z) = 489 [M + H] +.
[209] 127 mg (0.26 mmol) of 2-chloro-5- {1- [1-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl] -1H -imidazol-4-yl} benzoic acid, 42 mg (0.39 mmol) of benzylamine and 67 mg (0.52 mmol) of N, N-diethylisopropylamine are dissolved in a mixture of 4.6 ml of dichloromethane and 0.4 ml of N, N-dimethylformamide. 53 mg (0.39 mmol) of N-hydroxybenzotriazole and 60 mg (0.31 mmol) of N-ethyl-N '- (3-dimethylaminopropyl) carbodimide are added. The reaction mixture is stirred at room temperature for 16 h. The reaction solution is diluted with ethyl acetate and then washed successively with 1M hydrochloric acid, an aqueous solution of 1M sodium hydroxide and saturated sodium chloride solution. The crude product is purified by silica gel column chromatography.
[210] This provides 77 mg of N-benzyl-2-chloro-5- {1- [1-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazol-5-yl] -1H-imidazole -4-yl} benzamide as a colorless solid.
[211] 1H-NMR (400 MHz, d3-acetonitrile): δ = 7.94 (d, 1H), 7.88 (dd, 1H), 7.82 (d, 1H), 7.71 (d, 1H), 7.49 (d, 1H), 7.25 -7.43 (m, 5H), 4.56 (d, 2H), 3.73 (s, 3H) ppm.
[212] HPLC-MSa): logP = 4.00, mass spectrum (m / z) = 578 [M + H] +. a) Note regarding the determination of logP values and mass detection: The determination of the indicated logP values was carried out in accordance with EEC Directive 79/831 annex V.A8 by HPLC (High Performance Liquid Chromatography) in a column of reverse phase (C18). The Agilent 1100 LC system; 50 * 4.6 Zorbax Eclipse Plus C18 1.8 micron; mobile phase A: acetonitrile (0.1% formic acid); mobile phase B: water (0.09% formic acid); linear gradient from 10% acetonitrile to 95% acetonitrile in 4.25 min, then 95% acetonitrile for an additional 1.25 min; oven temperature of 55 ° C; flow rate: 2.0 mL / min. Mass detection is performed using an Agilend MSD system.
[213] The compounds listed in Tables 1 and 2 were prepared using Preparation Processes A to C described above. Table 1

Table 2

Table 3



























Table 4

Table 5



[214] The indicated mass is the peak of the [M + H] + ion isotope pattern of greatest intensity; if the ion [M-H] - was detected, the declared mass is marked with 2.
[215] 2 The indicated mass is the peak of the ion isotope pattern [M + H] - of the highest intensity. If the mass was determined by a GCMS measurement (see below for methods), the indicated mass is marked with 3.
[216] *) Note regarding the determination of logP values and mass detection: The determination of the supplied logP values was carried out in accordance with EEC Directive 79/831 annex V.A8 by HPLC (High Performance Liquid Chromatography) in an inverse phase column (C18). Agilent 1100 LC system; 50 * 4.6 Zorbax Eclipse Plus C18 1.8 micron; mobile phase A: acetonitrile (0.1% formic acid); mobile phase B: water (0.09% formic acid); linear gradient from 10% acetonitrile to 95% acetonitrile in 4.25 min, then 95% acetonitrile for an additional 1.25 min; oven temperature of 55 ° C; Flow rate: 2.0 mL / min. Mass detection is performed using an Agilend MSD system.
[217] **) Note on determining retention times. Measurement of retention time and associated mass spectra was performed using the following methods: a) Instruments: Micromass Quattro Premier with Waters UPLC Acquity; column: Thermo Hypersil GOLD 1.9 μ 50 x 1 mm; mobile phase A: 1 L of water + 0.5 ml of formic acid at 50% strength, mobile phase B: 1 L of acetonitrile + 0.5 ml of formic acid at 50% strength; gradient: 0.0 min 97% A ^ 0.5 min 97% A ^ 3.2 min 5% A ^ 4.0 min 5% A; oven: 50 ° C; flow rate: 0.3 mL / min; UV detection: 210 nm. b) Instruments: Waters ACQUITY UPLC SQD System; column: Waters Acquity UPLC HSS T3 1.8 μ 50 x 1 mm; mobile phase A: 1 L of water + 0.25 ml of formic acid at 99% strength, mobile phase B: 1 L of acetonitrile + 0.25 ml of formic acid at 99% strength; gradient: 0.0 min 90% A ^ 1.2 min 5% A ^ 2.0 min 5% A; oven: 50 ° C; flow rate: 0.40 mL / min; UV detection: 208-400 nm. c) MS instrument: Waters SQD; HPLC instrument: Waters UPLC; Column: Zorbax SB-AQ (Agilent), 50 mm x 2.1 mm, 1.8 μm; mobile phase A: water + 0.025% formic acid, mobile phase B: acetonitrile (ULC) + 0.025% formic acid; gradient: 0.0 min 98% A - 0.9 min 25% A - 1.0 min 5% A - 1.4 min 5% A - 1.41 min 98% A - 1.5 min 98% A; oven: 40 ° C; flow rate: 0.600 mL / min; UV detection: DAD; 210 nm. d) Instruments: Waters ACQUITY UPLC SQD System; column: Waters Acquity UPLC HSS T3 1.8 μ 50 x 1 mm; mobile phase A: 1 L of water + 0.25 ml of formic acid at 99% strength, mobile phase B: 1 L of acetronitrile + 0.25 ml of formic acid at 99% strength; gradient: 0.0 min 95% A ^ 6.0 min 5% A ^ 7.5 min 5% A; oven: 50 ° C; flow rate: 0.35 mL / min; UV detection: 210-400 nm. NMR data from selected Examples Peak NMR list method
[218] The 1H NMR data of the selected examples are indicated in the form of 1H NMR peak lists. For each signal peak, first the δ value in ppm and then the signal strength in parentheses are listed. The value δ - signal of pairs of intensity numbers for different signal peaks are listed with a semicolon separating each other.
[219] The peak list for an example, therefore, takes the form of: δ1 (intensity1); δ2 (intensity2); ; δi (intensityi); ; δn (intensity)
[220] The intensity of the acute signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal strengths. In the case of wide signals, several peaks or the middle of the signal and their relative intensities can be shown compared to the most intense signal in the spectrum.
[221] For the calibration of the chemical shift of the 1H NMR spectrum, we use tetramethylsilane and / or the chemical shift of the solvent, in particular, in the case of the spectra measured in DMSO. Therefore, the tetramethylsilane peak can, but need not, occur on peak NMR lists.
[222] The 1H NMR peak lists are similar to conventional 1H NMR impressions and therefore generally contain all of the peaks indicated in conventional NMR interpretation.
[223] In addition, as conventional 1H NMR prints, they may show signs of the solvent, signs of stereoisomers of the target compounds, which are also part of the aim of the invention, and / or peak impurities.
[224] When reporting signals from compounds in the solvent and / or water delta range, our 1H NMR peak lists show the usual solvent peaks, for example, DMSO peaks in DMSO-D6 and the water peak, which generally have a high intensity on average.
[225] The stereoisomers peaks of the target compounds and / or impurity peaks normally have a lower intensity, on average, than the peaks of the target compounds (for example,> 90% purity).
[226] Such stereoisomers and / or impurities may be typical of the particular preparation process. Its peaks can thus help in this case to identify reproduction of our preparation process with reference to "fingerprints by product".
[227] An expert calculating the peaks of the target compounds using known methods (MestReC, ACD simulation, but also with expected values evaluated empirically) can, if necessary, isolate the peaks of the target compounds, optionally, using filters of additional intensity. This isolation would be similar to the respective peak taking in the conventional 1H NMR interpretation.
[228] More details of the 1H NMR peak lists can be found in the Disclosure database search Number 564025.


















































Preparation of starting materials
[229] All starting materials used can be prepared by or analogous to processes known from the literature or are commercially available. Thus, for example, 5-fluoro-1-methyl-3- (pentafluoroethyl) -4- (trifluoromethyl) -1H-pyrazole can be prepared by a method known in the literature [Russian Chemical Bulletin 1990, 39, 11, 2338 - 2344 ].
[230] [4-Chloro-3- (methoxycarbonyl) phenyl] boronic acid, for example, is commercially available. Preparation of 2-chloro-N-cyclopropyl-5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzamide

[231] 75.0 g (318 mmol) of 5-bromo-2-chlorobenzoic acid are dissolved in 1.50 L of dimethylformamide, and 156 g (1.59 mol) of potassium acetate are added. The reaction mixture is degassed, 26.0 g (31.8 mmols) of 1,1'-bis (diphenylphosphine) ferrocenopalladium (II) dichloromethane are then added and the mixture is degassed again. The mixture is then heated at 80 ° C for 30 minutes and cooled again to room temperature. 121 g (477 mmol) of bis (pinacolate) diboro are then added, and the reaction mixture is stirred at 80 ° C for 4 h. After cooling to room temperature, the solvent is removed by distillation under reduced pressure. The residue is taken up in 500 ml of 2M aqueous sodium hydroxide solution. The aqueous phase is washed three times with 500 ml of ethyl acetate in each case. The aqueous phase is acidified with 2M hydrochloric acid, the resulting precipitated solid is filtered off and dried under reduced pressure.
[232] This provides 70.0 g of 2-chloro-5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzoic acid as a gray solid. This can be reacted, additionally, without any further purification.
[233] 1H-NMR (400 MHz, d6-dimethyl sulfoxide): δ = 8.05 (d, 1H), 7.76 (dd, 1H), 7.56 (d, 1H), 1.30 (s , 12H) ppm.
[234] 25.0 g (88.5 mmols) of 2-chloro-5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzoic acid are dissolved in 850 ml of dimethylformamide and 33.7 g (88.5 mmols) of HATU (1- [bis (dimethylamino) methylene] -1H-1,2,3-triazole [4,5-b] pyridinium hexafluorophosphate) are then added. The reaction is stirred at room temperature for 15 minutes. 35.4 ml (199 mmols) of N-ethyl-diisopropylamine and 7.50 ml (106 mmols) of cyclopropylamine are added to the reaction solution. After 16 h at room temperature, the solvent is removed by distillation under reduced pressure. The residue is taken up in water, and the product is subsequently extracted three times with, in each case, 500 ml of ethyl acetate. The combined organic phases are dried over sodium sulfate and filtered, and the solvent is removed under reduced pressure. The crude product is purified by silica gel column chromatography.
[235] This provides 16.6 g of 2-chloro-N-cyclopropyl-5- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzamide as a colorless solid.
[236] 1H-NMR (400 MHz, d6-dimethyl sulfoxide): δ = 8.50 (d, 1H), 7.66 (dd, 1H), 7.58 (d, 1H), 7.50 (d , 1H), 2.77-2.83 (m, 1H), 1.29 (s, 12H), 0.66-0.71 (m, 2H), 0.51- 0.55 (m, 2H ) ppm. Preparation of 5-chloro-1-methyl-4-nitro-3- (pentafluoroethyl) - 1H-pyrazole

[237] A little at a time, 3.80 g (70% purity, 13.2 mmol) of 1-methyl-3- (pentafluoroethyl) -1H-pyrazole [European Journal of Organic Chemistry 2002, 17, 2913-2920 ] are added to a mixture, heated to 70 ° C, of 5.79 ml of concentrated nitric acid (steaming) and 15.7 ml of concentrated sulfuric acid so that the internal temperature does not exceed 90 ° C. After the addition, the reaction solution is stirred at an internal temperature of 75 ° C for an additional 2h. After cooling the reaction mixture to room temperature, the reaction mixture is poured onto ice. The aqueous phase is extracted twice with 50 ml of ethyl acetate in each case. The combined organic phases are washed with 1N hydrochloric acid and saturated sodium chloride solution. The organic phase is dried over magnesium sulfate, filtered and concentrated on a rotary evaporator at reduced pressure. The crude product is purified by silica gel column chromatography.
[238] This provides 3.00 g of 1-methyl-4-nitro-3- (pentafluoroethyl) -1H-pyrazole.
[239] 1H-NMR (400 MHz, d3-acetronitrile): δ = 8.52 (d, 1H), 3.95 (s, 3H) ppm.
[240] HPLC-MS a): logP = 2.51 mass spectrum (m / z) = 246 [M + H] +.
[241] 980 mg (3.99 mmols) of 1-methyl-4-nitro-3- (pentafluoroethyl) -1H-pyrazole are dissolved in abs. THF, and the solution is cooled to -78 ° C. 3.00 mL (5.99 mmol) of a 2M solution of lithium diisopropylamide is added to this solution dropwise, and the mixture is stirred at -78 ° C for an additional 30 minutes. In a second flask, 947 mg (3.99 mmols) of hexachloroethane are charged initially dissolved in THF abs., And the solution is cooled to -78 ° C. The first solution is added slowly, drop by drop, to the second solution, such that the internal temperature does not exceed - 70 ° C. The reaction is stirred at -78 ° C for an additional hour. The reaction is quenched by the addition of saturated sodium bicarbonate solution. The reaction mixture is heated to RT. The mixture is extracted several times with ethyl acetate and the combined organic phases are dried over magnesium sulfate, filtered and concentrated on a rotary evaporator at 30 mbar (0.3 KPa) and a water bath temperature of 37 ° C.
[242] This provides 1.74 g (about 25% purity) of 5-chloro-1-methyl-4-nitro-3- (pentafluoroethyl) -1H-pyrazole. The crude product is reacted without further manipulation. Preparation of 1-methyl-4- (methylsulfanyl) -3- (trifluoromethyl) -1H-pyrazol-5-carboxylic acid

[243] Similarly to the preparation of 1-methyl- 4- (methylsulfanyl) -3- (pentafluoroethyl) -1H-pyrazol-5-carboxylic acid [WO2013-092522], 1-methyl-4- (methylsulfanyl) -3- (trifluoromethyl) -1H-pyrazol-5-carboxylic acid was prepared from 1-methyl-3- (trifluoromethyl) -1H-pyrazol-5-carboxylic acid.
[244] 1H-NMR (400 MHz, d6-DMSO-d6): δ = 4.10 (s, 3H), 2.34 (s, 3H) ppm.
[245] HPLC-MS a): logP = 1.72, mass spectrum (m / z) = 241 [M + H] +. Preparation of 1-methyl-4- (methylsulfanyl) -3- (trifluoromethyl) -1H-pyrazol-5-amine

[246] 600 mg (2.49 mmols) of 1-methyl-3- (trifluoromethyl) -1H-pyrazole-5-carboxylic acid is dissolved in a mixture of 40 ml of abs toluene. and 357 μL (2.56 mmols) of triethylamine. The solution is cooled to 0 ° C, and 704 mg (2.56 mmols) of diphenylphosphoryl azide is then added dropwise. The reaction mixture is stirred at an oil bath temperature of 100 ° C for 16 h. The mixture is cooled to room temperature and then carefully concentrated until dry on a rotary evaporator. The residue is taken up in 2 ml of tert-butanol and then heated in a microwave at 120 ° C for 1 h. The reaction mixture is concentrated to dryness on a rotary evaporator. The residue is taken up in 6 ml of dichloromethane, and 4.35 ml of trifluoroacetic acid are then added. The mixture is stirred at RT for 16 h. The reaction mixture is concentrated on a rotary evaporator. The residue is then taken up in ethyl acetate and washed twice with 1N aqueous sodium hydroxide solution, dried over sodium sulfate, filtered and concentrated on a rotary evaporator.
[247] The crude product is purified by silica gel column chromatography. This provides 130 mg of 1-methyl-4- (methylsulfanyl) -3- (trifluoromethyl) -1H-pyrazole-5-amine.
[248] 1H-NMR (400 MHz, d6-DMSO-d6): δ = 5.90 (s, 2H), 3.60 (s, 3H), 2.10 (s, 3H) ppm.
[249] HPLC-MS a): logP = 1.66 mass spectrum (m / z) = 212 [M + H] +. Preparation of 4-bromo-2'-methyl-4 '- (methylsulfinyl) -5'- (trifluoromethyl) -2'H-1,3'-bipyrazole

[250] 130 mg (0.61 mmol) of 1-methyl-4- (methylsulfanyl) -3- (trifluoromethyl) -1H-pyrazol-5-amine are dissolved in 14 ml of acetronitrile abs. and added, dropwise, to a suspension, heated at 70 ° C, of 146 μL (1.23 mmol) of tert-butyl nitrite, 99.3 mg (0.73 mmol) of copper (II) chloride and 29 mL of acetronitrile abs. The reaction mixture is stirred at 70 ° C for 7 h, cooled to room temperature and then poured into 75 ml of 1N hydrochloric acid. The crude product is extracted several times with ethyl acetate. The combined organic phases are washed twice with saturated sodium chloride solution, dried over magnesium sulfate, filtered and then concentrated until dry under reduced pressure and on a rotary evaporator.
[251] This provides, as a crude product, 219 mg of 5-chloro-1-methyl-4- (methylsulfanyl) -3- (trifluoromethyl) - 1H-pyrazole. The crude product was used without further purification.
[252] GC-MS: index = 1212, mass (m / z) = 230.
[253] 200 mg (about 60% content, about 0.52 mmol) of 5-chloro-1-methyl-4- (methylsulfanyl) -3- (trifluoromethyl) -1H-pyrazole are dissolved in 5 ml of dichloromethane pa and then cooled in an ice bath. 64 mg (content about 70%, 0.26 mmol) of 3-chloroperbenzoic acid are added a little at a time. The reaction is stirred with ice-cooling for an additional 3 h and then diluted with 30 ml of dichloromethane a.p. The organic phase is washed with saturated sodium bicarbonate solution until the organic phase is free of peroxide. The organic phase is then dried over sodium sulfate, filtered and concentrated until dry on a rotary evaporator under reduced pressure.
[254] This provides, as a crude product, 199 mg of 5-chloro-1-methyl-4- (methylsulfinyl) -3- (trifluoromethyl) -1H-pyrazole. The crude product is used for subsequent reactions without further purification.
[255] GC-MS: index = 1454, mass (m / z) = 246.
[256] 199 mg (content about 60%, 0.48 mmol) of 5-chloro-1-methyl-4- (methylsulfinyl) -3- (trifluoromethyl) -1H-pyrazole and 135 mg (0.88 mmol) of 4-bromo-1H-pyrazole are dissolved in 3 ml of dimethylformamide pa and 526 mg (1.61 mmol) of cesium carbonate are then added. The reaction mixture is heated to an oil bath temperature of 100 ° C until no starting material is detected. The mixture is filtered and diluted with methyl tert-butyl ether. The organic phase is then washed with 1N hydrochloric acid and saturated sodium chloride solution. The organic phase is then dried over sodium sulfate and concentrated on a rotary evaporator under reduced pressure. The crude product is then purified by silica gel column chromatography.
[257] This provides 61 mg of 4-bromo-2'-methyl-4'- (methylsulfinyl) -5 '- (trifluoromethyl) -2'H-1,3'-bipyrazole.
[258] 1H-NMR (400 MHz, d3-acetronitrile): δ = 8.13 (s, 1H), 7.91 (s, 1H), 3.77 (s, 3H), 2.73 (s, 3H) ppm.
[259] HPLC-MS a): logP = 1.90 mass spectrum (m / z) = 359 [M + H] +. Examples of biological work for applications in sector I of animal health. A. Amblyomma hebaraeum (AMBYHE) test Solvent: dimethyl sulfoxide
[260] To produce a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide, and the concentrate is diluted with water to the desired concentration.
[261] Tick larvae (Amblyomma hebraeum) are placed in perforated plastic beakers and immersed in the desired concentration for one minute. Ticks are transferred on filter paper to a Petri dish and stored in a temperature-controlled chamber.
[262] After 42 days, death in% is determined. 100% means that all ticks have been killed; 0% means that none of the ticks were killed.
[263] In this test, for example, the following compounds from the preparation examples reveal 100% effectiveness at an application rate of 100 ppm: Ia-1, Ia-2, Ib-3, Ic-1, Ic-2 , Ic-11, Ic-16, Ic-21, Ic-23, Ic-24, Ic-27, Ic-34, Ic-36, Ic-37, Ic-47, Ic-49, Ic-83, Ic -84, Ic-85, Ic-87, Ic-91, Ic-94, Ic-95. B. Boophilus microplus - immersion test (BOOPMI Dip) Test animals: bovine ticks (Boophilus microplus) Parkhurst strain, resistant SP Solvent: dimethyl sulfoxide
[264] 10 mg of the active compound are dissolved in 0.5 ml of dimethyl sulfoxide. For the purpose of preparing a suitable formulation, the active compound solution is diluted with water to the desired concentration in each case.
[265] This active compound preparation is pipetted into tubes. 8-10 Female swallowed adult bovine ticks (Boophilus microplus) are transferred to a new tube with holes. The tube is immersed in the formulation of the active compound, and all ticks are completely moist. After the liquid runs out, the ticks are transferred to filter discs on plastic plates and stored in a heated room.
[266] Activity is assessed after 7 days by laying fertile eggs. Eggs whose fertility is not visible from the outside are stored in a climate controlled chamber until the larvae hatch after about 42 days. 100% effectiveness means that none of the ticks has established any fertile eggs; 0% means that all eggs are fertile.
[267] In this test, for example, the following compounds of Preparation Examples reveal 100% effectiveness at an application rate of 100 ppm: Ia-1, Ia-2, Ib-2, Ib-3, Ic-1 , IC-2, IC-11, IC-16, IC-21, IC-23, IC-24, IC-27, IC-34, IC-36, IC-37, IC-47, IC-49, IC -65, IC-66, IC-77, IC-78, IC-81, IC-83, IC-84, IC-85, IC-86, IC-87, IC-90, IC-91, IC-94 , Ic-95, Ic-96, Ic-109, Ic-111, Ic-112, Ic-113, Ic-130, Ic-139, Ic-147, Ic-151, Ic-152, Ic-153, Ic -158, Ic-160, Ic-164, Ic-166.
[268] In this test, for example, the following compounds from the preparation examples reveal 90% effectiveness at an application rate of 100 ppm: Ic-97, Ic-103, Ic-175.
[269] In this test, for example, the following compounds from the preparation examples show 80% effectiveness at an application rate of 100 ppm: Ic-29, Ic-48, Ic-80, Ic-159. C. Boophilus microplus - injection test (BOOPMI Inj) Solvent: dimethyl sulfoxide
[270] To produce a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of solvent, and the concentrate is diluted with solvent to the desired concentration.
[271] 1 μL of the active compound solution is injected into the abdomen of 5 engorged adult female bovine ticks (Boophilus microplus). The animals are transferred to dishes and kept in a room with controlled climate.
[272] Activity is assessed after 7 days by laying fertile eggs. Eggs whose fertility is not visible from the outside are stored in a climate controlled chamber until the larvae hatch after about 42 days. 100% effectiveness means that none of the ticks has established any fertile eggs; 0% means that all eggs are fertile.
[273] In this test, for example, the following compounds from the preparation examples reveal 100% effectiveness at an application rate of 20 μg / animal: Ia-1, Ia- 2, Ib-2, Ib-3, Ic -1, IC-2, IC-3, IC-4, IC-6, IC-7, IC-8, IC-10, IC-11, IC-12, IC-13, IC-14, IC-16 , IC-17, IC-18, IC-19, IC-20, IC-21, IC-22, IC-23, IC-24, IC-25, IC-27, IC-28, IC-29, IC -32, IC-33, IC-34, IC-36, IC-37, IC-38, IC-39, IC-40, IC-41, IC-42, IC-43, IC-44, IC-46 , IC-47, IC-48, IC-49, IC-53, IC-54, IC-55, IC-56, IC-58, IC-59, IC-60, IC-61, IC-62, IC -63, IC-64, IC-65, IC-66, IC-67, IC-68, IC-70, IC-71, IC-72, IC-73, IC-74, IC-75, IC-76 , IC-77, IC-78, IC-80, IC-81, IC-83, IC-84, IC-85, IC-86, IC-87, IC-88, IC-89, IC-90, IC -91, IC-92, IC-94, IC-95, IC-96, IC-97, IC-99, IC-103, IC-106, IC-136, IC-137, IC-139, IC-140 , Ic-147, Ic-149, Ic-150, Ic-151, Ic-152, Ic-153, Ic-154, Ic-157, Ic-158, Ic-159, Ic-160, Ic-161, Ic -163, Ic-164, Ic-165, Ic-166, Ic-174, Ic-175, Id-1, Id-2, Ie-1.
[274] In this test, for example, the following compounds from the preparation examples reveal 90% effectiveness at an application rate of 20 μg / animal: Ic-156.
[275] In this test, for example, the following compounds from the preparation examples reveal 80% efficacy at an application rate of 20 μg / animal: Ic-15, Ic-35. D. Ctenocephalides felis - oral test (CTECFE ) Solvent: dimethyl sulfoxide
[276] To produce a suitable preparation of active compound, 10 mg of the active compound are mixed with 0.5 ml of dimethyl sulfoxide. Dilution with blood from citrated cattle provides the desired concentration.
[277] About 20 fasting adult cat fleas (Ctenocephalides felis) are placed inside a chamber, which is closed at the top and bottom with gauze. A metal cylinder, the bottom of which is closed with a plastic paraffin film, is placed over the chamber. The cylinder contains the blood / active ingredient preparation, which can be absorbed by the fleas through the plastic paraffin membrane.
[278] After 2 days, death in% is determined. 100% means that all fleas have been killed; 0% means that none of the fleas have been killed.
[279] In this test, for example, the following compounds from the preparation examples reveal 100% effectiveness at an application rate of 100 ppm: Ia-1, Ia-2, Ib-2, Ib-3, Ic-1 , Ic-2, Ic-3, Ic-4, Ic-6, Ic-7, Ic-8, Ic-11, Ic-12, Ic-13, Ic-16, Ic-18, Ic-19, Ic -20, IC-21, IC-22, IC-23, IC-24, IC-27, IC-28, IC-29, IC-31, IC-32, IC-33, IC-34, IC-35 , IC-36, IC-37, IC-38, IC-39, IC-40, IC-41, IC-42, IC-43, IC-44, IC-45, IC-46, IC-47, IC -48, IC-49, IC-53, IC-54, IC-55, IC-56, IC-57, IC-58, IC-59, IC-60, IC-61, IC-64, IC-65 , Ic-66, Ic-67, Ic-68, Ic-70, Ic-71, Ic-73, Ic-74, Ic-75, Ic-76, Ic-77, Ic-78, Ic-80, Ic -81, IC-83, IC-84, IC-85, IC-86, IC-87, IC-90, IC-91, IC-94, IC-95, IC-96, IC-97, IC-99 , IC-103, IC-106, IC-136, IC-137, IC-139, IC-140, IC-147, IC-149, IC-150, IC-151, IC-152, IC-153, IC -154, Ic-156, Ic-158, Ic-159, Ic-160, Ic-161, Ic-163, Ic-164, Ic-165, Ic-166, Ic-174, Ic-175, Id-1 , Id-2, Ie-1.
[280] In this test, for example, the following compounds from the preparation examples reveal 98% effectiveness at an application rate of 100 ppm: Ic-10.
[281] In this test, for example, the following compounds of the preparation examples reveal 95% effectiveness at an application rate of 100 ppm: Ic-25, Ic-62, Ic-63.
[282] In this test, for example, the following compounds from the preparation examples reveal 90% effectiveness at an application rate of 100 ppm: Ic-17, Ic-89, Ic-157.
[283] In this test, for example, the following compounds from the preparation examples reveal 80% effectiveness at an application rate of 100 ppm: Ic-92. E. Lucilia cuprine test (LUCICU) Solvent: dimethyl sulfoxide
[284] To produce a suitable preparation of the active compound, 10 mg of the active compound are mixed with 0.5 ml of dimethyl sulfoxide, and the concentrate is diluted with water to the desired concentration.
[285] About 20 L1 larvae of the Australian sheep blowfly (Lucilia cuprina) are transferred to a test vessel containing minced horse meat and the preparation of the active compound to the desired concentration.
[286] After 2 days, death in% is determined. 100% means that all larvae have been killed; 0% means that none of the larvae have been killed.
[287] In this test, for example, the following compounds from the preparation examples reveal 100% effectiveness at an application rate of 100 ppm: Ia-1, Ia-2, Ib-2, Ib-3, Ic-1 , Ic-2, Ic-3, Ic-4, Ic-6, Ic-7, Ic-8, Ic-10, Ic-11, Ic-12, Ic-13, Ic-14, Ic-16, Ic -17, IC-18, IC-19, IC-20, IC-21, IC-22, IC-23, IC-24, IC-25, IC-27, IC-28, IC-29, IC-32 , IC-33, IC-34, IC-35, IC-36, IC-37, IC-38, IC-39, IC-40, IC-41, IC-42, IC-43, IC-44, IC -45, IC-46, IC-47, IC-48, IC-49, IC-53, IC-54, IC-55, IC-56, IC-57, IC-58, IC-59, IC-60 , IC-61, IC-62, IC-63, IC-64, IC-65, IC-66, IC-67, IC-68, IC-70, IC-71, IC-73, IC-74, IC -75, IC-76, IC-77, IC-78, IC-80, IC-81, IC-83, IC-84, IC-85, IC-86, IC-87, IC-88, IC-89 , IC-90, IC-91, IC-94, IC-95, IC-96, IC-97, IC-103, IC-106, IC-136, IC-137, IC-140, IC-147, IC -149, Ic-150, Ic-151, Ic-152, Ic-153, Ic-154, Ic-157, Ic-158, Ic-159, Ic-160, Ic-161, Ic-163, Ic-164 , Ic-165, Ic-166, Ic-174, Ic-175, Id-1.
[288] In this test, for example, the following compounds from the preparation examples reveal 95% effectiveness at an application rate of 100 ppm: Ic-92, Id-2.
[289] In this test, for example, the following compounds from the preparation examples reveal 90% effectiveness at an application rate of 100 ppm: Ic-31.
[290] In this test, for example, the following compounds from the preparation examples reveal 80% effectiveness at an application rate of 100 ppm: Ic-72, Ic-99. F. Musca domestica (MUSCDO) test Solvent: dimethyl sulfoxide
[291] To produce a suitable active compound preparation, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide, and the concentrate is diluted with water to the desired concentration.
[292] Vases containing a sponge treated with a sugar solution and the preparation of active compound with the desired concentration are populated with 10 adult house flies (Musca domestica).
[293] After 2 days, death in% is determined. 100% means that all the flies have been killed; 0% means that none of the flies were killed.
[294] In this test, for example, the following compounds from the preparation examples reveal 100% effectiveness at an application rate of 100 ppm: Ib-2, Ib-3, Ic-1, Ic-2, Ic-3 , IC-7, IC-11, IC-12, IC-16, IC-18, IC-19, IC-21, IC-23, IC-24, IC-27, IC-28, IC-29, IC -32, IC-33, IC-34, IC-36, IC-37, IC-38, IC-39, IC-40, IC-41, IC-43, IC-45, IC-46, IC-47 , IC-48, IC-49, IC-55, IC-57, IC-59, IC-60, IC-62, IC-65, IC-66, IC-70, IC-77, IC-78, IC -80, IC-81, IC-83, IC-84, IC-85, IC-86, IC-87, IC-90, IC-91, IC-94, IC-95, IC-96, IC-97 , Ic-106, Ic-147, Ic-151, Ic-152, Ic-153, Ic-159, Ic-160, Ic-166, Ic-174, Ic-175, Id-1.
[295] In this test, for example, the following compounds from the preparation examples reveal 95% effectiveness at an application rate of 100 ppm: Ic-67.
[296] In this test, for example, the following compounds from the preparation examples reveal 90% effectiveness at an application rate of 100 ppm:: Ia-2, Ic-6, Ic-25, Ic-73, Ic- 136, Ic-140, Ic-154, Ic-158, Ic-163, Ic-164.
[297] In this test, for example, the following compounds from the preparation examples reveal 80% effectiveness at an application rate of 100 ppm: Ia-1, Ic-44, Ic-58, Ic-61, Ic-64 , Ic-68, Ic-71, Ic-76, Ic-103, Ic-161. Biological working examples for applications in the crop protection sector G. Myzus Persicae - spray test (MYZUPE) Solvents: 78 parts by weight of acetone 1.5 parts by weight of dimethylformamide Emulsifier: alkylaryl polyglycol ether
[298] To produce a suitable preparation of active compound, 1 part by weight of the active compound is dissolved using the parts indicated by weight of solvent and constituted with water comprising an emulsifying concentration of 1000 ppm until the desired concentration is reached. To produce higher test concentrations, the preparation is diluted with water containing emulsifier.
[299] The discs of Chinese cabbage leaves (Brassica pekinensis) infested by all stages of the green aphid (Myzus persicae) are sprayed with an active compound preparation of the desired concentration.
[300] After 6 days, the effectiveness in%, is determined. 100% here means that all aphids have been killed; 0% means that no aphids have been killed.
[301] In this test, for example, the following compounds of the preparation examples reveal 100% effectiveness at an application rate of 500 g / ha: Ic-40, Ic-41, Ic-47, Ic-55, Ic -71, IC-84, IC-85, IC-86, IC-90, IC-91, IC-94, IC-97, IC-139, IC-141, IC-147, IC-151, IC-152 , Ic-159, Ic-181, Ic-188.
[302] In this test, for example, the following compounds from the preparation examples show 90% effectiveness at an application rate of 500 g / ha: Ic-1, Ic-24, Ic-27, Ic-49, Ic -70, Ic-95, Ic-116, Ic-117, Ic-153, Ic-156, Ic-163, Ic-164, Ic-166, Ic-167, Ic-180, Ic-187.
[303] In this test, for example, the following compounds from the preparation examples reveal 100% effectiveness at an application rate of 100 g / ha: Ic-2, Ic-11, Ic-77, Ic-96, Ic -109, Ic-111, Ic-112, Ic-118, Ic-121, Ic-126, Ic-127, Ic-133, Ic-134, Ic-182, Ic-185, Ic-190.
[304] In this test, for example, the following compounds from the preparation examples reveal 90% effectiveness at an application rate of 100 g / ha: Ib-2, Ic-28, Ic-34, Ic-36, Ic -48, IC-65, IC-66, IC-78, IC-79, IC-80, IC-81, IC-87, IC-108, IC-113, IC-115, IC-122, IC-129 , Ic-132, Ic-147, Ic-186. H. Phaedon cochleariae - spray test (PHAECO) Solvents: 78.0 parts by weight of acetone 1.5 parts by weight of dimethylformamide Emulsifier: alkylaryl polyglycol ether
[305] To produce a suitable preparation of active compound, 1 part by weight of the active compound is dissolved using the parts indicated by weight of solvent and constituted with water comprising a concentration of 1000 ppm of emulsifying agent until the desired concentration is reached. To produce higher test concentrations, the preparation is diluted with water containing emulsifier.
[306] The disks of Chinese cabbage leaves (Brassica pekinensis) are sprayed with a preparation of active compound with the desired concentration and, after drying, populated with larvae of the mustard beetle (Phaedon cochleariae).
[307] After 7 days, the effectiveness in%, is determined. 100% means that all larvae of the beetle have been killed; 0% means that none of the beetle's larvae have been killed.
[308] In this test, for example, the following compounds from the preparation examples reveal 100% effectiveness at an application rate of 500 g / ha: Ic-1, Ic-24, Ic-27, Ic-33, Ic -38, IC-39, IC-40, IC-41, IC-42, IC-43, IC-44, IC-45, IC-46, IC-47, IC-48, IC-49, IC-51 , IC-52, IC-54, IC-55, IC-56, IC-58, IC-59, IC-60, IC-61, IC-62, IC-63, IC-64, IC-70, IC -71, IC-72, IC-73, IC-74, IC-75, IC-76, IC-84, IC-85, IC-86, IC-87, IC-88, IC-89, IC-90 , IC-91, IC-92, IC-93, IC-94, IC-95, IC-97, IC-105, IC-106, IC-107, IC-116, IC-117, IC-136, IC -139, Ic-140, Ic-141, Ic-142, Ic-147, Ic-149, Ic-150, Ic-151, Ic-152, Ic-153, Ic-154, Ic-156, Ic-157 , Ic-159, Ic-161, Ic-163, Ic-164, Ic-165, Ic-166, Ic-167, Ic-171, Ic-173, Ic-174, Ic-175, Ic-176, Ic -179, Ic-180, Ic-181, Ic-183, Ic-184, Ic-186, Ic-187, Ic-188, Ic-193, Ic-198, Ic-200.
[309] In this test, for example, the following compounds from the preparation examples reveal an 83% efficiency at an application rate of 500 g / ha: Ic-69, Ic-137.
[310] In this test, for example, the following compounds from the preparation examples reveal 100% effectiveness at an application rate of 100 g / ha: Ia-1, Ia-2, Ib-2, Ib-3, Ic -2, Ic-3, Ic-6, Ic-7, Ic-10, Ic-11, Ic-12, Ic-13, Ic-14, Ic-15, Ic-16, Ic-17, Ic-18 , IC-19, IC-20, IC-21, IC-22, IC-23, IC-25, IC-28, IC-29, IC-30, IC-31, IC-32, IC-34, IC -35, IC-36, IC-37, IC-53, IC-65, IC-66, IC-67, IC-68, IC-78, IC-79, IC-80, IC-81, IC-83 , Ic-96, Ic-99, Ic-103, Ic-104, Ic-108, Ic-109, Ic-110, Ic-111, Ic-113, Ic-115, Ic-118, Ic-119, Ic -121, Ic-122, Ic-124, Ic-125, Ic-126, Ic-127, Ic-128, Ic-129, Ic-130, Ic-131, Ic-132, Ic-133, Ic-134 , IC-168, IC-169, IC-170, IC-177, IC-178, IC-182, IC-185, IC-189, IC-190, IC-191, IC-192, Id-1, Id -2, Ie-1, Ie-4, Ie-5.
[311] In this test, for example, the following compounds from the preparation examples reveal an 83% efficiency at an application rate of 100 g / ha: Ib-1, Ic-5, Ic-57, Ic-120, Ic -135. I. Spodoptera frugiperda - spray test (SPODFR) Solvent: 78.0 parts by weight of acetone 1.5 parts by weight of dimethylformamide Emulsifier: alkyl aryl polyglycol ether
[312] To produce a suitable active compound preparation, 1 part by weight of the active compound is dissolved using the parts indicated by weight of solvent and constituted with water comprising a concentration of 1000 ppm of emulsifying agent until the desired concentration is reached . To produce higher test concentrations, the preparation is diluted with water containing emulsifier.
[313] Corn leaf discs (Zea mays) are sprayed with an active compound preparation of the desired concentration and, after drying, populated with caterpillars of the corn cartridge larvae (Spodoptera frugiperda).
[314] After 7 days, the effectiveness in%, is determined. 100% means that all caterpillars have been killed; 0% means that none of the caterpillars were killed.
[315] In this test, for example, the following compounds from the preparation examples reveal 100% effectiveness at an application rate of 500 g / ha: Ic-1, Ic-24, Ic-27, Ic-38, Ic -39, IC-40, IC-41, IC-43, IC-44, IC-45, IC-46, IC-47, IC-48, IC-49, IC-55, IC-59, IC-60 , IC-62, IC-70, IC-71, IC-73, IC-74, IC-75, IC-76, IC-84, IC-85, IC-86, IC-87, IC-90, IC -91, IC-94, IC-95, IC-97, IC-105, IC-107, IC-116, IC-117, IC-136, IC-139, IC-140, IC-141, IC-142 , Ic-147, Ic-149, Ic-150, Ic-151, Ic-152, Ic-153, Ic-154, Ic-156, Ic-157, Ic-159, Ic-161, Ic-163, Ic -164, Ic-165, Ic-166, Ic-167, Ic-171, Ic-174, Ic-175, Ic-176, Ic-180, Ic-181, Ic-183, Ic-184, Ic-186 , Ic-187, Ic-188, Ic-193, Ic-198, Ic-200.
[316] In this test, for example, the following compounds from the preparation examples show 83% efficiency at an application rate of 500 g / ha: Ic-33, Ic-42, Ic-89, Ic-106.
[317] In this test, for example, the following compounds from the preparation examples reveal 100% effectiveness at an application rate of 100 g / ha: Ia-1, Ia-2, Ib-2, Ib-3, Ic -2, Ic-3, Ic-6, Ic-7, Ic-10, Ic-11, Ic-12, Ic-13, Ic-14, Ic-16, Ic-17, Ic-18, Ic-19 , IC-20, IC-21, IC-22, IC-23, IC-25, IC-28, IC-29, IC-32, IC-34, IC-36, IC-37, IC-39, IC -61, IC-64, IC-66, IC-73, IC-77, IC-78, IC-79, IC-80, IC-81, IC-83, IC-96, IC-103, IC-109 , IC-110, IC-111, IC-112, IC-113, IC-115, IC-118, IC-122, IC-124, IC-126, IC-127, IC-128, IC-129, IC -131, Ic-132, Ic-133, Ic-135, Ic-169, Ic-170, Ic-177, Ic-182, Ic-185, Ic-190, Id-1, Id-2.
[318] In this test, for example, the following compounds from the preparation examples reveal an 83% efficiency at an application rate of 100 g / ha: Ic-68, Ic-65, Ic-108, Ic-119, Ic -125, Ic-168. J. Tetranychus urticae - spray test, OP-resistant (TETRUR) Solvent: 78.0 parts by weight of acetone 1.5 parts by weight of dimethylformamide Emulsifier: alkyl aryl polyglycol ether
[319] To produce a suitable preparation of active compound, 1 part by weight of the active compound is dissolved using the parts indicated by weight of solvent and constituted with water comprising a concentration of 1000 ppm of emulsifying agent until the desired concentration is reached . To produce higher test concentrations, the preparation is diluted with water containing emulsifier.
[320] The bean leaf discs (Phaseolus vulgaris) that are infested by all stages of the greenhouse spider mite (Tetranychus urticae) are sprayed with an active compound preparation of the desired concentration.
[321] After 6 days, the effectiveness in% is determined. 100% means that all the mites have died; 0% means that none of the mites have been killed.
[322] In this test, for example, the following compounds of the Preparation Examples show, at an application rate of 500 g / ha, a 100% effectiveness: Ic-1, Ic-24, Ic-27, Ic-40 , IC-41, IC-71, IC-84, IC-85, IC-86, IC-87, IC-91, IC-94, IC-95, IC-97, IC-107, IC-116, IC -117, IC-136, IC-137, IC-139, IC-140, IC-141, IC-142, IC-147, IC-149, IC-150, IC-151, IC-152, IC-153 , Ic-154, Ic-156, Ic-157, Ic-159, Ic-161, Ic-163, Ic-164, Ic-165, Ic-166, Ic-167, Ic-175, Ic-176, Ic -180, Ic-181, Ic-183, Ic-184, Ic-187, Ic-188, Ic-193, Ic-198, Ic-200.
[323] In this test, for example, the following compounds from the preparation examples reveal 90% effectiveness at an application rate of 500 g / ha: Ic-49, Ic-69, Ic-90, Ic-105, Ic -171, Ic-186.
[324] In this test, for example, the following compounds of the preparation examples show 80% efficiency at an application rate of 500 g / ha: Ic-44, Ic-55, Ic-76.
[325] In this test, for example, the following compounds from the preparation examples reveal 100% efficiency at an application rate of 100 g / ha: Ia-1, Ib-2, Ib-3, Ic-2, Ic -10, IC-17, IC-19, IC-20, IC-21, IC-22, IC-23, IC-28, IC-32, IC-34, IC-36, IC-37, IC-39 , IC-63, IC-64, IC-65, IC-66, IC-67, IC-68, IC-73, IC-77, IC-78, IC-79, IC-80, IC-81, IC -83, IC-96, IC-99, IC-103, IC-104, IC-108, IC-109, IC-110, IC-111, IC-112, IC-113, IC-115, IC-118 , Ic-119, Ic-120, Ic-121, Ic-122, Ic-123, Ic-124, Ic-125, Ic-126, Ic-127, Ic-128, Ic-129, Ic-131, Ic -132, Ic-133, Ic-134, Ic-135, Ic-168, Ic-169, Ic-170, Ic-177, Ic-185, Ic-189, Ic-190.
[326] In this test, for example, the following compounds from the preparation examples show 90% effectiveness at an application rate of 100 g / ha: Ia-2, Ic-3, Ic-9, Ic-11, Ic -13, Ic-48, Ic-56, Ic-59, Ic-182. K. Meloidogyne incognita test (MELGIN) Solvent: 125.0 parts by weight of acetone
[327] To prepare a suitable active compound preparation, 1 part by weight of the active compound is mixed with the indicated amount of the solvent and the concentrate is diluted with water to the desired concentration.
[328] The pots are filled with sand, the active compound solution, a suspension of eggs / larvae from the southern root nodules (Meloidogyne incognita) and lettuce seeds. Lettuce seeds germinate and plants grow. In the roots, galls are formed.
[329] After 14 days, nematicidal efficacy in% is determined by gall formation. 100% means that no gall was found; 0% means that the number of galls in the treated plants corresponds to that of the untreated control.
[330] In this test, for example, the following compounds from the preparation examples reveal 100% effectiveness at an application rate of 20 ppm: Ic-152.
[331] In this test, for example, the following compounds of the preparation examples reveal a 90% efficiency of an application rate of 20 ppm: Ic-1, Ic-26, Ic-120, Ic-156. Examples of biological work for applications in sector II of animal health: T1. Ctenocephalides felis - in in vitro contact tests with adult cat fleas
[332] For the lining of the test tubes, initially 9 mg of the active compound are dissolved in 1 ml of acetone p.a. and then diluted with acetone p.a. to the desired concentration. When rotating and swinging on an orbital shaker (2 hr swing rotation at 30 rpm), 250 μl of the solution are homogeneously distributed on the internal walls and the floor of a 25 mL test tube. At 900 ppm, the active compound solution and 44.7 cm2 of the internal surface, an area dose of 5 μg / cm2 is achieved for homogeneous distribution.
[333] After solvent evaporation, the tubes are populated with 5-10 adult cat fleas (Ctenocephalides felis), sealed with a perforated plastic cover and incubated in a horizontal position at room temperature and room humidity. After 48 h, effectiveness is determined. To this end, the test tubes were in an upright position and the fleas are propelled on the floor of the tube. Fleas that remain motionless on the floor or move in an uncoordinated way are considered dead or dying.
[334] A substance shows good activity against Ctenocephalides felis if, in this test, at least 80% efficacy was achieved at an application rate of 5 μg / cm2. 100% effectiveness means that all flies were dead or dying. 0% means that no flea efficacy had been damaged.
[335] In this test, for example, the following compounds from the preparation examples reveal 100% effectiveness at an application rate of 5 μg / cm2: Ia-1, Ia-2, Ib-2, Ib-3, Ic -1, IC-2, IC-11, IC-12, IC-16, IC-18, IC-19, IC-21, IC-23, IC-24, IC-27, IC-28, IC-29 , IC-34, IC-36, IC-37, IC-41, IC-47, IC-48, IC-49, IC-65, IC-66, IC-68, IC-70, IC-71, IC -77, IC-78, IC-81, IC-83, IC-84, IC-85, IC-86, IC-87, IC-90, IC-91, IC-94, IC-95, IC-96 , Ic-97, Ic-107, Ic-108, Ic-109, Ic-110, Ic-111, Ic-112, Ic-113, Ic-118, Ic 139, Ic-140, Ic-141, Ic- 142, Ic-143, Ic-144, Ic-145, Ic 147, Ic-148, Ic-149, Ic-151, Ic-152, Ic-153, Ic-155, Ic 158, Ic-159, Ic- 160, Ic-163, Ic-164, Ic-165, Ic-166, Ic-167, Ic-175, Ic-199, Ic-211.
[336] In this test, for example, the following compounds from the preparation examples reveal an 80% efficiency at an application rate of 5 μg / cm2: Ic-32, Ic-138, Ic-146, Ic-154.
[337] In this test, for example, the following compounds from the preparation examples reveal 100% effectiveness at an application rate of 1 μg / cm2: Ia-1, Ia-2, Ib-2, Ib-3, Ic -1, IC-2, IC-11, IC-12, IC-16, IC-18, IC-19, IC-21, IC-23, IC-24, IC-27, IC-28, IC-29 , IC-34, IC-36, IC-37, IC-41, IC-47, IC-48, IC-49, IC-65, IC-66, IC-70, IC-71, IC-77, IC -78, IC-81, IC-83, IC-84, IC-85, IC-86, IC-87, IC-90, IC-91, IC-94, IC-95, IC-96, IC-97 , Ic-107, Ic-108, Ic-109, Ic-111, Ic-112, Ic-113, Ic-118, Ic-139, Ic-140, Ic-141, Ic-142, Ic-143, Ic -144, Ic-145, Ic-147, Ic-151, Ic-152, Ic-153, Ic-154, Ic-155, Ic-158, Ic-159, Ic-160, Ic-163, Ic-163 , Ic-164, Ic-165, Ic-166, Ic-167, Ic-175, Ic-199, Ic-211.
[338] In this test, for example, the following compounds from the preparation examples reveal 80% effectiveness at an application rate of 1 μg / cm2: Ic-146, Ic-149. T2. Rhipicephalus sanguineus - in vitro contact tests with brown adult dog ticks
[339] For the coating of the test tubes, initially 9 mg of the active compound are dissolved in 1 ml of acetone p.a. and then diluted with acetone p.a. to the desired concentration. When rotating and swinging on an orbital shaker (2 hr swing rotation at 30 rpm), 250 μl of the solution are homogeneously distributed over the inner walls and the floor of a 25 mL test tube. At 900 ppm the active compound solution and 44.7 cm2 of the internal surface, an area dose of 5 μg / cm2 is achieved for homogeneous distribution.
[340] After solvent evaporation, the tubes are populated with 5-10 adult dog ticks (Rhipicephalus sanguineus), sealed with a perforated plastic cover and incubated in a horizontal position, in the dark, at room temperature and room humidity. After 48 h, effectiveness is determined. For this purpose, the ticks are pushed on the floor of the tube and incubated on a heating plate at 45-50 ° C for a maximum of 5 min. Ticks that have remained motionless on the ground or move in an uncoordinated way in such a way that they are not able to deliberately avoid the rising heat are considered dead or dying.
[341] A substance shows good activity against Rhipicephalus sanguineus if, in this test, at least 80% efficacy was achieved with an application rate of 5 μg / cm2. 100% effectiveness means that all mites have been killed or dying. 0% means that no effectiveness of the mites has been damaged.
[342] In this test, for example, the following compounds from the preparation examples reveal 100% effectiveness at an application rate of 5 μg / cm2: Ia-1, Ia-2, Ic-1, Ic-2, Ic -11, IC-16, IC-18, IC-21, IC-23, IC-24, IC-25, IC-27, IC-28, IC-34, IC-36, IC-37, IC-47 , IC-48, IC-49, IC-54, IC-66, IC-70, IC-71, IC-77, IC-78, IC-81, IC-83, IC-84, IC-85, IC -86, IC-87, IC-90, IC-94, IC-95, IC-96, IC-103, IC-106, IC-109, IC-111, IC-112, IC-113, IC-141 , Ic-142, Ic-143, Ic-151, Ic-152, Ic-155, Ic-160, Ic-161, Ic-164, Ic-166,
[343] Ic-167, In this Ic-174, test, Ic-201. for example, the following compounds from the preparation examples show 80% efficiency at an application rate of 5 μg / cm2: Ib-3, Ic-19, Ic-61, Ic-73, Ic-91, Ic-108 , Ic-153.
[344] In this test, for example, the following compounds in the preparation examples reveal 100% efficacy at an application rate of 1 μg / cm2: Ia-1, Ia-2, Ib-3, Ic-1, Ic -2, IC-11, IC-16, IC-18, IC-19, IC-21, IC-23, IC-24, IC-25, IC-27, IC-36, IC-37, IC-43 , IC-46, IC-47, IC-48, IC-49, IC-54, IC-59, IC-66, IC-68, IC-70, IC-77, IC-78, IC-81, IC -83, IC-84, IC-85, IC-86, IC-87, IC-90, IC-94, IC-95, IC-96, IC-103, IC-109, IC-111, IC-112 , IC-143, IC-151, IC-152, IC-155, IC-160, IC-163, IC-164, IC-166, IC-167, IC-174, IC-201.
[345] In this test, for example, the following compounds from the preparation examples reveal 80% effectiveness at an application rate of 1 μg / cm2: Ic-32, Ic-34, Ic-67, Ic-71, Ic -73, Ic-113, Ic-141, Ic-142, Ic-147, Ic-148, Ic-153, Ic-161. T3. Ixodes ricinus - in vitro contact tests with adult castor bean ticks
[346] For the coating of the test tubes, initially 9 mg of the active compound are dissolved in 1 ml of acetone p.a. and then diluted with acetone p.a. to the desired concentration. When rotating and swinging on an orbital shaker (2 hr swing rotation at 30 rpm), 250 μl of the solution are homogeneously distributed over the internal walls and the floor of a 25 mL test tube. At 900 ppm the active compound solution and 44.7 cm2 of the internal surface, an area dose of 5 μg / cm2 is achieved for homogeneous distribution.
[347] After solvent evaporation, the tubes are populated with 5-10 adult castor bean ticks (Ixodes ricinus), sealed with a perforated plastic cover and incubated in a horizontal position, in the dark, at 22 ° C and 90% humidity in a climate controlled chamber. After 48 h, effectiveness is determined. For this purpose, the ticks are pushed on the floor of the tube and incubated on a heating plate at 45-50 ° C for a maximum of 5 min. Ticks that have remained motionless on the ground or move in an uncoordinated way in such a way that they are not able to deliberately avoid the rising heat are considered dead or dying.
[348] A substance shows good activity against Ixodes ricinus if, in this test, an efficacy of at least 80% was achieved with an application rate of 5 μg / cm2. 100% effectiveness means that all mites have been killed or dying. 0% means that none of the ticks' effectiveness has been damaged.
[349] In this test, for example, the following compounds from the preparation examples reveal 100% effectiveness at an application rate of 5 μg / cm2: Ia-1, Ia-2, Ic-1, Ic-2, Ic -11, IC-16, IC-21, IC-23, IC-37, IC-47, IC-48, IC-81, IC-83, IC-84, IC-86, IC-87, IC-90 , Ic-94.
[350] In this test, for example, the following compounds from the preparation examples reveal an 80% effectiveness at an application rate of 5 μg / cm2: Ib-3, Ic-18.
[351] In this test, for example, the following compounds from the preparation examples show 100% effectiveness at an application rate of 1 μg / cm2: Ia-1, Ia-2, Ic-1, Ic-2, Ic- 16, IC-23, IC-37, IC-81, IC-84, IC-90, IC-94.
[352] In this test, for example, the following compounds from the preparation examples reveal 80% effectiveness at an application rate of 1 μg / cm2: Ib-3, Ic-11, Ic-21, Ic-48, Ic -86, IC-87. T4. Amblyomma hebraeum - in vitro contact tests with tick larvae
[353] For the lining of the test tubes, initially 9 mg of the active compound are dissolved in 1 ml of acetone p.a. and then diluted with acetone p.a. to the desired concentration. When rotating and swinging on an orbital shaker (2 hr swing rotation at 30 rpm), 250 μL of the solution are homogeneously distributed over the internal walls and the floor of a 25 mL test tube. At 900 ppm, the active compound solution and 44.7 cm2 of the internal surface, an area dose of 5 μg / cm2 is achieved for homogeneous distribution.
[354] After solvent evaporation, the tubes are populated with 5-10 mite larvae (Amblyomma hebraeum), sealed with a perforated plastic cover and incubated in a horizontal position, in the dark, at 27 ° C and 85% humidity in a climate controlled chamber. After 48 h, effectiveness is determined. For this purpose, the ticks are pushed on the floor of the tube and incubated on a heating plate at 45-50 ° C for a maximum of 5 min. Ticks that have remained motionless on the ground or move in an uncoordinated way in such a way that they are not able to deliberately avoid the rising heat are considered dead or dying.
[355] A substance shows good activity against Amblyomma hebraeum larvae if, in this test, an efficiency of at least 80% was achieved with an application rate of 5 μg / cm2. 100% effectiveness means that all mites have been killed or dying. 0% means that none of the ticks' effectiveness has been damaged.
[356] In this test, for example, the following compounds from the preparation examples reveal 100% effectiveness at an application rate of 5 μg / cm2: Ia-1, Ia-2, Ib-2, Ib-3, Ic -1, IC-2, IC-3, IC-11, IC-16, IC-18, IC-19, IC-21, IC-23, IC-32, IC-37, IC-47, IC-48 , IC-49, IC-81, IC-83, IC-84, IC-86, IC-87, IC-90, IC-94, IC-95.
[357] In this test, for example, the following compounds from the preparation examples reveal 100% effectiveness at an application rate of 1 μg / cm2: Ia-1, Ia-2, Ib-2, Ic-1, Ic -2, IC-11, IC-16, IC-18, IC-19, IC-21, IC-23, IC-32, IC-37, IC-47, IC-48, IC-81, IC-83 , IC-84, IC-86, IC-87, IC-90, IC-94, IC-95.
[358] In this test, for example, the following compounds from the preparation examples show 80% efficiency at an application rate of 1 μg / cm2: Ib-3, Ic-3. T6. Dermacentor variabilis - in vivo systemic activity against American dog tick larvae in rats
[359] In a randomized, open placebo-controlled study, the effectiveness of preparation examples of the halogen substituted compounds of formula (I) according to the invention against larvae of the American dog tick (Dermacentor variabilis) in rats (Rattus norvegicus ; strain: Whistar Unilever, HsdCpb: WU) is examined after intraperitoneal treatment. For this purpose, a suitable amount of the active compound is dissolved in the formal glycerol and injected intraperitoneally. The volume administered is, depending on the concentration of active compound, between 30 and 90 μL / 100 g of body weight. 5 rats per group are used, the results are reported as arithmetic means. Prior to mite infestations, all mice are provided with collars. For tick infestation and counting, rats are sedated with 30-50 μL of medetomidine hydrochloride (eg Domitor®) s.c./rat. All rats are infested on day 0 (at least 1 hour after treatment), day 7, day 14, etc., with 30 non-engorged Dermacentor variabilis larvae. On day 2, day 9, day 16, etc., the collar is removed and the entire body of the sedated rats is systematically examined for ticks. Ticks are removed with tweezers and because they are crushed on blotting paper, examined with sucked blood.
[360] The effectiveness of treatment is determined by comparison with a placebo-treated control group. A compound is considered to be highly effective if, at a dosage of 10 mg / kg, it shows a 90% effectiveness against larvae of American dog ticks (Dermacentor variabilis) on day 2 after intraperitoneal treatment. The effect is considered to be more lasting if the effectiveness on day 9 is even higher than 80%.
[361] In this test, for example, the following compounds from the preparation examples reveal> 90% efficacy against tick larvae on day 2 at an application rate of 10 mg / kg: Ic-1, Ic-2.
[362] In this test, for example, the following compounds in the preparation examples reveal> 80% efficacy against tick larvae on day 9 at an application rate of 10 mg / kg: Ic-1, Ic-2. T7. Ctenocephalides felis - in vivo systemic activities against fleas in rats
[363] In a randomized, open placebo-controlled study, the effectiveness of preparation examples of the halogen-substituted compounds of formula (I) according to the invention against adult cat fleas (Ctenocephalides felis) in rats (Rattus norvegicus; strain : Unilever Whistar, HsdCpb: WU) is examined after intraperitoneal treatment. For this purpose, a suitable amount of the active compound is dissolved in the formal glycerol and injected intraperitoneally. The volume administered is, depending on the concentration of the active compound, between 30 and 90 μL / 100 g of body weight. 5 rats per group are used, the results are reported as arithmetic means. Prior to flea infestations, all mice are provided with collars. For flea infestation and counting, the rats are sedated with 30-50 μL of medetomidine hydrochloride (eg Domitor®) s.c./ rat. All rats are infested on day 0 (at least 1 hour after treatment), day 7, day 14, etc., with 30 fasting adult Ctenocephalides felis. On day 2, day 9, day 16, etc., the collar is removed and the entire body of the sedated rats is systematically examined for fleas using a flea comb. Fleas are counted and removed.
[364] Treatment effectiveness is determined by comparison with a placebo-treated control group. A compound is considered to be highly effective if, at a dosage of 10 mg / kg, it shows 95% efficacy against adult fleas (Ctenocephalides felis) on day 2 after intraperitoneal treatment. The effect is considered to be more lasting if the effectiveness on day 9 is still greater than 90%.
[365] In this test, for example, the following compounds in the preparation examples reveal> 95% efficacy against fleas on day 2 at an application rate of 10 mg / kg: Ic-1, Ic-2.
[366] In this test, for example, the following compounds from the preparation examples show> 90% efficacy against fleas on day 9 at an application rate of 10 mg / kg: Ic-1, Ic-2 T8. - Haemonchus contortus (HAEMCO) test Solvent: dimethyl sulfoxide
[367] To produce a suitable active compound preparation, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide, and the concentrate is diluted with "Ringer's solution" to the desired concentration.
[368] Vases containing the preparation of active compound with the desired concentration are populated with about 40 larvae of the stomach red worm (Haemonchus contortus).
[369] After 5 days, death in% is determined. 100% means that all larvae have been killed; 0% means that none of the larvae have been killed.
[370] In this test, for example, the following compounds from the preparation examples show 80% effectiveness at an application rate of 20 ppm: Ic-1, Ic-16.

权利要求:
Claims (11)
[0001]
1. Compound characterized by having the general formula (I):
[0002]
Compound according to claim 1, characterized by having the following structure:
[0003]
Compound according to claim 2, characterized by having the following structure:
[0004]
4. Use of the compound of the general formula (I) or (Ic), as defined in claim 1 or 2, characterized by being for the control of insects, arachnids and nematodes.
[0005]
Pharmaceutical composition characterized in that it comprises at least one compound, as defined in claim 1 or 2.
[0006]
Compound according to claim 1 or 2, characterized in that it is for use as medicaments.
[0007]
7. Use of the compound, as defined in claim 1 or 2, characterized in that it is for the preparation of pharmaceutical compositions for the control of parasites in animals.
[0008]
8. Process for the preparation of crop protection compositions characterized by comprising the compound, as defined in claim 1 or 2, and the usual diluents and / or surfactants.
[0009]
9. Pest control method characterized by a compound, as defined in claim 1 or 2, to act on pests and / or in their habitat, in which surgical, therapeutic and diagnostic treatment of the human or animal body are excluded.
[0010]
10. Use of the compound, as defined in claim 1 or 2, characterized by being for the protection of plant propagation material.
[0011]
11. Compound characterized by being 4-bromo-2'-methyl-4 '- (methylsulfinyl) -5' - (trifluoromethyl) -2'H-1,3'-bipyrazole. (I) R1 represents hydrogen, optionally substituted with C1-C6 alkyl, C3-C6 alkenyl, C3-C6 alkynyl, C3-C7 cycloalkyl, C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, aryl- (C1- C3) -alkyl, heteroaryl- (C1-C3) -alkyl; R1 represents hydrogen, optionally substituted with C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C7 cycloalkyl, C1-C6 alkylcarbon, C1-C6 alkoxycarbonyl, aryl- (C1- C3) -alkyl, heteroaryl- ( C1-C3) -alkyl; chemical groups: A1 represents CR2 or nitrogen; A2 represents CR3 or nitrogen; A3 represents CR4 or nitrogen; and A4 represents CR5 or nitrogen; 2 4 (I-1)

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HUE036065T2|2018-06-28|

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KR20150116439A|2015-10-15|

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CR20150392A|2015-11-26|

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US20150353500A1|2015-12-10|

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IL240112A|2019-01-31|

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法律状态:
2019-07-30| B06U| Preliminary requirement: requests with searches performed by other patent offices: suspension of the patent application procedure|

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2020-02-18| B07A| Technical examination (opinion): publication of technical examination (opinion)|

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2020-05-26| B06A| Notification to applicant to reply to the report for non-patentability or inadequacy of the application according art. 36 industrial patent law|

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2020-09-29| B09A| Decision: intention to grant|

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2020-12-15| B25A| Requested transfer of rights approved|Owner name: BAYER ANIMAL HEALTH GMBH (DE) |

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2021-01-05| B16A| Patent or certificate of addition of invention granted|Free format text: PRAZO DE VALIDADE: 20 (VINTE) ANOS CONTADOS A PARTIR DE 03/02/2014, OBSERVADAS AS CONDICOES LEGAIS. |

优先权:

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申请号 | 申请日 | 专利标题

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EP13154269.8|2013-02-06|

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EP13154269|2013-02-06|

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EP13180076|2013-08-12|

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EP13180076.5|2013-08-12|

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PCT/EP2014/051989|WO2014122083A1|2013-02-06|2014-02-03|Halogen-substituted pyrazol derivatives as pest-control agents|

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