(3-Pyridyl)-quinazoline

Abstract

The present invention relates to a compound represented by formula (I) [Formula 1] TIFF2024528144000055.tif38170, where the variables are defined as set forth in the description and claims. The present invention further relates to their uses and compositions.

Description

[Technical field]

[0001] The present invention relates to (3-pyridyl)-quinazoline compounds and their N-oxides and salts as fungicides and to their use. The present invention also relates to compositions comprising at least one compound I, to a method for combating plant pathogens and to seeds coated with at least one compound of formula I. [Background technology]

[0002] Japanese Patent Publication No. 2011148714 discloses some similar compounds. However, in many cases, the fungicidal activity of known compounds is not satisfactory, especially at low application rates. Based on this, it was an object of the present invention to provide compounds with improved activity and / or a broader activity spectrum against plant pathogens. Another object of the present invention is to provide fungicides with improved toxicological properties or with improved environmental fate properties. Summary of the Invention [Means for solving the problem]

[0003] These and further objects are achieved by the pyridine compounds of formula (I) and their agriculturally preferred forms, as defined below. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0004] The present invention therefore provides compounds of formula I as fungicides. [ka] [In the formula, R 1 is H, halogen, CN, C1-C4 alkyl, C1-C4 halogen alkyl; R 2is independently selected at each occurrence from halogen, CN, C1-C6 alkyl, C1-C6 halogen alkyl, C2-C6 alkenyl, C2-C6 halogen alkenyl, C2-C6 alkynyl, C2-C6 halogen alkynyl, O-C1-C6 alkyl, O-C2-C6 alkenyl, O-C2-C6 alkynyl, C3-C6 cycloalkyl; R 3 is independently selected at each occurrence from halogen, CN, C1-C6 alkyl, C1-C6 halogen alkyl, C2-C6 alkenyl, C2-C6 halogen alkenyl, C2-C6 alkynyl, C2-C6 halogen alkynyl, O-C1-C6 alkyl, O-C2-C6 alkenyl, O-C2-C6 alkynyl, C3-C6 cycloalkyl; R 4 is H, halogen, CN, C1-C4 alkyl, C1-C4 halogen alkyl; R 5 is independently selected at each occurrence from halogen, CN, C1-C6 alkyl, C1-C6 halogen alkyl, C2-C6 alkenyl, C2-C6 halogen alkenyl, C2-C6 alkynyl, C2-C6 halogen alkynyl, phenyl, and benzyl; Here, R 5 The phenyl and benzyl moieties of 5a and which groups are, independently of one another, Selected from halogen, CN, C1-C6 alkyl, C1-C6 halogen alkyl, and O-C1-C6 alkyl; R 6 is independently selected at each occurrence from halogen, CN, C1-C6 alkyl, C1-C6 halogen alkyl, C2-C6 alkenyl, C2-C6 halogen alkenyl, C2-C6 alkynyl, C2-C6 halogen alkynyl, phenyl, and benzyl; Here, R 6 The phenyl and benzyl moieties of 6a and which groups are, independently of one another, Selected from halogen, CN, C1-C6 alkyl, C1-C6 halogen alkyl, and O-C1-C6 alkyl; or R 5 and R 6 form together with the C atom to which they are attached a 3-6 membered saturated heterocycle containing 1, 2 or 3 heteroatoms from the group consisting of C3-C6 cycloalkyl or O and S; R 7 is in each case hydrogen, CN, CH2CN, CH(CH3)CN, CH(=O), C(=O)C1-C6 alkyl, C(=O)C2-C6 alkenyl, C(=O)C2-C6 alkynyl, C(=O)C3-C6 cycloalkyl, C(=O)NH-C1-C4 alkyl, C(=O)N-(C1-C4 alkyl) 2、 C1-C6 alkyl, O-C1-C6 alkyl, C1-C4 halogen alkyl, C3-C6 cycloalkyl, C3-C6 halogen cycloalkyl, C2-C6 alkenyl, C2-C6 halogen alkenyl, C2-C6 alkynyl, C2-C6 halogen alkynyl, -S(=O)2-R 7a , 5- or 6-membered heteroaryl and aryl or benzyl; where heteroaryl contains 1, 2 or 3 heteroatoms selected from N, O and S; where the aryl or benzyl group is unsubstituted or has 1, 2, 3, 4 or 5 substituents selected from the group consisting of CN, halogen, OH, C1-C4 alkyl, C1-C4 halogen alkyl, C1-C4 alkoxy and C1-C4 halogen alkoxy; where R 7a is selected from C1-C6 alkyl, C1-C6 halogen alkyl, C2-C6 alkenyl, C2-C6 halogen alkenyl, C2-C6 alkynyl, C2-C6 halogen alkynyl, phenyl, benzyl, where phenyl and benzyl can be unsubstituted or substituted by halogen, C1-C6 alkyl, C1-C6 halogen alkyl, C2-C6 alkenyl, C2-C6 halogen alkenyl, C2-C6 alkynyl, C2-C6 halogen alkynyl; X, at each occurrence, is independently selected from halogen, CN, C1-C6 alkyl, C1-C6 halogenalkyl, O-C1-C6 alkyl, and O-C1-C6 halogenalkyl; n is 0, 1, 2 or 3. and their N-oxides and agriculturally acceptable salts.

[0005] N-oxides can be prepared from the compounds of the invention by treating compound I according to conventional oxidation methods, for example with organic peracids such as metachloroperbenzoic acid (see WO 03 / 64572 or J. Med. Chem. 38(11), 1892-903, 1995); or with inorganic oxidizing agents such as hydrogen peroxide (see J. Heterocyc. Chem. 18(7), 1305-8, 1981) or oxone (see J. Am. Chem. Soc. 123(25), 5962-5973, 2001). The oxidation can lead to pure mono-N-oxides or to mixtures of different N-oxides, which can be separated by conventional methods, such as chromatography.

[0006] Agriculturally acceptable salts of the compounds of formula I include, inter alia, the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, do not adversely affect the fungicidal action of compound I. Suitable cations are therefore, in particular, the ions of alkali metals, preferably sodium and potassium, the ions of alkaline earth metals, preferably calcium, magnesium and barium, the ions of transition metals, preferably manganese, copper, zinc and iron, and also the ammonium ions, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, which may, if desired, be substituted with 1 to 4 C1-C4 alkyl substituents and / or one phenyl or benzyl substituent, and furthermore phosphonium ions, sulfonium ions, preferably tri(C1-C4 alkyl)sulfonium, and sulfoxonium ions, preferably tri(C1-C4 alkyl)sulfoxonium ions.

[0007] Acceptable anions of the acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and anions of C1-C4 alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting compound I with an acid of the corresponding anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

[0008] The compounds of formula I can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers resulting from restricted rotation around a single bond of asymmetric groups. They also form part of the subject matter of the present invention. Those skilled in the art will appreciate that one stereoisomer may be more active and / or may show beneficial effects when enriched with respect to other stereoisomers or separated from other stereoisomers. Furthermore, those skilled in the art know how to separate, enrich and / or selectively prepare said stereoisomers. The compounds of the present invention may exist as mixtures of stereoisomers, such as racemates, as individual stereoisomers or as optically active forms.

[0009] The compounds of formula I can exist in different crystal modifications whose biological activity may differ, which also form part of the subject-matter of the present invention.

[0010] In terms of variables, the embodiments of intermediates obtained during the preparation of compound I correspond to the embodiments of the compound of formula I. The term "compound I" refers to the compound of formula I.

[0011] Below, intermediate compounds are further described.Those skilled in the art will easily understand that the preferences for substituents, in particular the preferences for the substituents shown in the following table for each substituent shown herein in connection with compound I, also apply accordingly to intermediates.Therefore, the substituents in each case, independently of each other or more preferably in combination, have the meanings as defined herein.

[0012] If synthesis results in a mixture of isomers, separation is generally not necessary, since in some cases the individual isomers can be interconverted during preparation for use or during application (e.g. under the action of light, acid or base). Such conversions can also occur after use, for example in the treatment of plants in treated plants or in harmful fungi to be controlled.

[0013] In the above definitions of the variables, generic terms are used that generally represent the substituents of interest. n ~C m " indicates the possible number of carbon atoms in each case in the substituent or substituent moiety in question.

[0014] The term "halogen" refers to fluorine, chlorine, bromine and iodine.

[0015] The term "C1-C6 alkyl" refers to a straight-chain or branched saturated hydrocarbon group having 1 to 6 carbon atoms, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, and 1-ethyl-2-methylpropyl. Similarly, the term "C2-C4 alkyl" refers to a straight or branched alkyl group having 2 to 4 carbon atoms, such as ethyl, propyl (n-propyl), 1-methylethyl (iso-propyl), butyl, 1-methylpropyl (sec.-butyl), 2-methylpropyl (iso-butyl), 1,1-dimethylethyl (tert.-butyl).

[0016] The term "C1-C6 halogen alkyl" refers to an alkyl group having 1 or 6 carbon atoms as defined above, in which some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as described above. Examples are "C1-C2 halogen alkyl" groups, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl or pentafluoroethyl.

[0017] The term "C1-C6 alkoxy" refers to a straight or branched alkyl group having 1 to 6 carbon atoms attached via an oxygen at any position in the alkyl group. Examples are "C1-C4 alkoxy" groups such as methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy.

[0018] The term "C1-C6 halogenalkoxy" refers to C1-C6 alkoxy groups as defined above, in which some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as defined above. Examples are "C1-C4 halogen alkoxy" groups such as OCH2F, OCHF2, OCF3, OCH2Cl, OCHCl2, OCCl3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC2F5, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2 chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3 Examples include bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH2-C2F5, OCF2-C2F5, 1-fluoromethyl-2-fluoroethoxy, 1-chloromethyl-2-chloroethoxy, 1-bromomethyl-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy, and nonafluorobutoxy.

[0019] The term "C2-C6 alkenyl" refers to a straight or branched unsaturated hydrocarbon group having 2-6 carbon atoms and a double bond at any position. Examples are "C2-C4 alkenyl" groups such as ethenyl, 1-propenyl, 2-propenyl (allyl), 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, etc.

[0020] The term "C2-C6 halogen alkenyl" refers to alkyl groups having 2 or 6 carbon atoms as defined above, in which some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as defined above.

[0021] The term "C2-C6 alkenyloxy" refers to a straight or branched alkenyl group having 2 to 6 carbon atoms attached via an oxygen at any position of the alkenyl group. An example is a "C2-C4 alkenyloxy" group.

[0022] The term "C2-C6 alkynyl" refers to a straight or branched unsaturated hydrocarbon group having 2 to 6 carbon atoms and containing at least one triple bond. Examples are "C2-C4 alkynyl" groups such as ethynyl, prop-1-ynyl, prop-2-ynyl (propargyl), but-1-ynyl, but-2-ynyl, but-3-ynyl, 1-methyl-prop-2-ynyl, and the like.

[0023] The term "C2-C6 halogen alkynyl" refers to alkyl groups having 2 or 6 carbon atoms as defined above, in which some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as defined above.

[0024] The term "C2-C6 alkynyloxy" refers to a straight or branched alkynyl group having 2 to 6 carbon atoms attached via an oxygen at any position of the alkynyl group. An example is a "C2-C4 alkynyloxy" group.

[0025] The term "C3-C6 cycloalkyl" refers to a monocyclic saturated hydrocarbon group having 3 to 6 carbon ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like. Thus, a saturated 3-, 4-, 5-, 6-, 7-, 8-, 9-, or 10-membered carbocyclyl or carbocycle is a "C3-C 10 "Cycloalkyl".

[0026] The term "C3-C6 cycloalkenyl" refers to a monocyclic partially unsaturated 3-, 4-, 5-, or 6-membered carbocyclic ring having 3 to 6 carbon ring members and at least one double bond, such as cyclopentenyl, cyclopentadienyl, cyclohexadienyl, and the like. Thus, a partially unsaturated 3-, 4-, 5-, 6-, 7-, 8-, 9-, or 10-membered carbocyclyl or carbocyclic ring is defined as "C3-C 10 "Cycloalkenyl".

[0027] The term "C3-C8 cycloalkyl-C1-C4 alkyl" refers to an alkyl having 1 to 4 carbon atoms (as defined above) in which one hydrogen atom of the alkyl group is replaced with a cycloalkyl group having 3 to 8 carbon atoms (as defined above).

[0028] The term "saturated or partially unsaturated 3, 4, 5, 6, 7, 8, 9 or 10 membered heterocyclyl or heterocycle, where the heterocyclyl or heterocycle contains 1, 2, 3 or 4 heteroatoms selected from N, O and S" should be understood to mean both saturated and partially unsaturated heterocycles, where the ring atoms of the heterocycle include, in addition to carbon atoms, 1, 2, 3 or 4 heteroatoms independently selected from the group O, N and S. For example: 3- or 4-membered saturated heterocycles containing one or two heteroatoms from the group consisting of O, N and S as ring members, such as oxirane, aziridine, thiirane, oxetane, azetidine, thietane, [1,2]dioxetane, [1,2]dithietane, [1,2]diazetidine, etc.; and 5- or 6-membered saturated or partially unsaturated heterocycles containing 1, 2 or 3 heteroatoms from the group consisting of O, N and S as ring members, such as 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, zolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofuran-2-yl, 2,3 -Dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin 4-isothiazolin-5-yl, 2-isoxazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol -4-yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1,3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, 1,3,5-hexahydrotriazin-2-yl and 1,2,4-hexahydrotriazin-3-yl, and also the corresponding -ylidene radicals; and Seven-membered saturated or partially unsaturated heterocycles, such as tetra- and hexahydroazepinyl, for example 2,3,4,5-tetrahydro[1H]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl, 3,4,5,6-tetrahydro[2H]azepin-2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,4,7-tetrahydro[1H]azepin-2-, -3-, -4-, -5-, -6- or -7-yl, azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,6,7-tetrahydro[1H]azepin-1-, -2-, -3-, -4-, -5-, -6- or -7-yl, hexahydroazepin-1-, -2-, -3- or -4-yl, tetra- and hexahydrooxepinyl, for example 2,3,4,5-tetrahydro[1H]oxepinyl, hexahydroazepine-1-, -2-, -3- or -4-, such as 2,3,4,7-tetrahydro[1H]oxepin-2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,6,7-tetrahydro[1H]oxepin-2-, -3-, -4-, -5-, -6- or -7-yl; -yl, tetra- and hexahydro-1,3-diazepinyl, tetra- and hexahydro-1,4-diazepinyl, tetra- and hexahydro-1,3-oxazepinyl, tetra- and hexahydro-1,4-oxazepinyl, tetra- and hexahydro-1,3-dioxepinyl, tetra- and hexahydro-1,4-dioxepinyl and the corresponding -ylidene groups.

[0029] The term "substituted" refers to substituted with 1, 2, 3 or up to the maximum number of substituents possible.

[0030] The term "5- or 6-membered heteroaryl" or "5- or 6-membered heteroaromatic" refers to an aromatic ring system that contains, in addition to carbon atoms, one, two, three, or four heteroatoms independently selected from the group consisting of N, O, and S, e.g., 5-membered heteroaryl, such as pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1,2,4-triazolyl-1-yl, 1,2,4-triazol-3-yl 1,2,4-triazol-5-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl and 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, etc.; or 6-membered heteroaryl, such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl and 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl says.

[0031] In the following, specific embodiments of the compounds of the invention are described, in which specific meanings of the respective substituents are further elaborated, where these meanings are in each case specific embodiments of the invention by themselves, but also in any combination with one another.

[0032] Furthermore, with regard to the variables, in general, the embodiments of compounds I also apply to the intermediates.

[0033] According to one embodiment of the compound of formula I, R 1 is H, halogen, CN, C1-C4 alkyl, C1-C4 halogen alkyl.

[0034] According to one embodiment of the compound of formula I, R 1 is H.

[0035] According to one embodiment of the compound of formula I, R 1 is CH3.

[0036] According to one embodiment of the compound of formula I, R 2 is selected from halogen, CN, C1-C6 alkyl, C1-C6 halogen alkyl, C2-C6 alkenyl, C2-C6 halogen alkenyl, C2-C6 alkynyl, C2-C6 halogen alkynyl, O-C1-C6 alkyl, O-C2-C6 alkenyl, O-C2-C6 alkynyl, and C3-C6 cycloalkyl.

[0037] According to yet another embodiment of formula I, R 2 is halogen, in particular F, Cl, Br or l, more in particular F, Cl or Br, especially F or Cl.

[0038] According to yet another embodiment of formula I, R 2 is F.

[0039] According to yet another embodiment of formula I, R 2 is Cl.

[0040] According to yet another embodiment of formula I, R 2 is Br.

[0041] According to yet another embodiment of formula I, R 2 is CN.

[0042] According to yet another embodiment of formula I, R 2 is C1-C6 alkyl, in particular C1-C4 alkyl, such as CH3 or C2H5, in particular CH3 or CH2CH3.

[0043] According to yet another embodiment of formula I, R 2 is C1-C6 halogen alkyl, particularly C1-C4 halogen alkyl, such as CF3.

[0044] According to yet a further embodiment of formula I, R 2 is C2-C6 alkenyl, particularly C2-C4 alkenyl, such as CH=CH2, C(CH3)=CH2, CH2CH=CH2, etc.

[0045] According to a more specific embodiment of formula I, R 2 is C2-C6 halogen alkenyl, particularly C2-C4 halogen alkenyl, more particularly C2-C3 halogen alkenyl, such as CH=CHF, CH=CHCl, CH=CF2, CH=CCl2, CH2CH=CHF, CH2CH=CHCl, CH2CH=CF2, CH2CH=CCl2, CF2CH=CF2, CCl2CH=CCl2, CF2CF=CF2, CCl2CCl=CCl2, etc.

[0046] According to yet a further embodiment of formula I, R 2 is C2-C6 alkynyl or C2-C6 halogen alkynyl, in particular C2-C4 alkynyl or C2-C4 halogen alkynyl, for example C≡CH, CH2C≡CH, C≡CCl, CH2C≡CCl, or CCl2C≡CCl.

[0047] According to a further specific embodiment of formula I, R 2 is O-C1-C6 alkyl, particularly C1-C4 alkyl, more particularly C1-C2 alkoxy. R 2 is, for example, OCH3 or OCH2CH3.

[0048] According to a further specific embodiment of formula I, R 2 is O-C1-C6 alkyl.

[0049] According to a further specific embodiment of formula I, R 2 is O-C2-C6 alkenyl, particularly C2-C4 alkenyl, more particularly C2-C3 alkenyl. R 2 For example, OCH=CH2, OCH2CH=CH2, etc.

[0050] According to a further specific embodiment of formula I, R 2 is O-C2-C6 alkynyl, particularly C2-C6 alkynyl, especially C2-C4 alkynyl, more especially C2-C3 alkynyl. R 2 For example, O-CH2-C≡CH.

[0051] According to yet another embodiment of formula I, R 2 is C3-C6 cycloalkyl, in particular cyclopropyl or cyclobutyl.

[0052] R according to the present invention 2 Particularly preferred embodiments of are found in Table P2 below, where each row of P2-1 to P2-21 corresponds to one particular embodiment of the invention, where P2-1 to P2-21 are also preferred embodiments of the invention in any combination with each other. 2 The attachment point to the carbon atom to which is bonded is marked with a "#" in the drawing.

[0053] [Table 1]

[0054] According to one embodiment of formula I, R 3 is selected from the group consisting of C1-C6 alkyl, C1-C6 halogen alkyl, C3-C6 cycloalkyl, particularly CH3, C2H5, CF3, CH2F, CHF2, cyclopropyl, cyclobutyl, more particularly CH3, CH2F, CF2H, CF3, cyclopropyl, cyclobutyl, most preferably CH3, CF3, CF2H.

[0055] According to yet another embodiment of formula I, R 3 is C1-C6 alkyl, particularly C1-C4 alkyl, such as CH3 or C2H5, particularly CH3 or CH2CH3.

[0056] According to yet another embodiment of formula I, R 3is C1-C6 halogen alkyl, particularly C1-C4 halogen alkyl, such as CF3, FCH2, F2CH, CF3CH2, etc.

[0057] According to yet a further embodiment of formula I, R 3 is C2-C6 alkenyl, particularly C2-C4 alkenyl, such as CH=CH2, C(CH3)=CH2, CH2CH=CH2, etc.

[0058] According to yet a further embodiment of formula I, R 3 is C2-C6 alkynyl or C2-C6 halogen alkynyl, in particular C2-C4 alkynyl or C2-C4 halogen alkynyl, such as C≡CH, CH2C≡CH, C≡CCl, CH2C≡CCl, or CCl2C≡CCl.

[0059] According to a further specific embodiment of formula I, R 3 is O-C1-C6 alkyl, particularly C1-C4 alkyl, more particularly C1-C2 alkoxy. R 3 is, for example, OCH3 or OCH2CH3.

[0060] According to a further specific embodiment of formula I, R 3 is O-C2-C6 alkenyl, particularly C2-C4 alkenyl, more particularly C2-C3 alkenyl. R 3 For example, OCH=CH2, OCH2CH=CH2, etc.

[0061] According to a further specific embodiment of formula I, R 3 is O-C2-C6 alkynyl, particularly C2-C6 alkynyl, especially C2-C4 alkynyl, more especially C2-C3 alkynyl. R 3 For example, O-CH2-C≡CH.

[0062] According to a further specific embodiment of formula I, R 3is O-C1-C6 halogen alkyl, in particular OCF3, OCCl3, OFCH2, OClCH2, OF2CH, OCl2CH, OCF3CH2, OCCl3CH2 or OCF2CHF2, more in particular OCF3, OF2CH, OFCH2.

[0063] According to yet another embodiment of formula I, R 3 is C3-C6 cycloalkyl, particularly cyclopropyl, cyclobutyl.

[0064] R according to the present invention 3 Particularly preferred embodiments of are found in Table P3 below, where each row of P3-1 to P3-17 corresponds to one particular embodiment of the invention, where P3-1 to P3-17 are also preferred embodiments of the invention in any combination with each other. 3 The attachment point to the carbon atom to which is bonded is marked with a "#" in the drawing.

[0065] [Table 2]

[0066] According to one embodiment of the compound of formula I, R 4 is H, halogen, CN, C1-C4 alkyl, C1-C4 halogen alkyl.

[0067] According to one embodiment of the compound of formula I, R 4 is H.

[0068] According to one embodiment of the compound of formula I, R 4 is CH3.

[0069] R 5 is independently selected at each occurrence from halogen, CN, C1-C6 alkyl, C1-C6 halogen alkyl, C2-C6 alkenyl, C2-C6 halogen alkenyl, C2-C6 alkynyl, C2-C6 halogen alkynyl, C1-C6 alkyl-O-C1-C6 alkyl, phenyl, and benzyl; Here, R 5The phenyl and benzyl moieties of are unsubstituted or contain 1 to 3 groups R 5a and which groups are, independently of one another, It is selected from halogen, CN, C1-C6 alkyl, C1-C6 halogen alkyl, and O-C1-C6 alkyl.

[0070] According to one embodiment of the compound of formula I, R 5 is independently selected in each occurrence from C1-C6 alkyl (embodiment 5.1), C1-C6 halogen alkyl (embodiment 5.2), C1-C6 alkyl-O-C1-C6 alkyl (embodiment 5.3), phenyl, CH2-phenyl (embodiment 5.4), halogen (embodiment 5.5), where phenyl and CH2-phenyl are unsubstituted or substituted by 1 or 2 halogens.

[0071] According to a further embodiment of the compound of formula I, R 5 is CH3 or CF3.

[0072] According to a further embodiment of the compound of formula I, R 5 are CH2CH3, CH(CH3)2, CH(CH3)CH2CH3, C(CH3)3, CH2-CH(CH3)2, CH2-C(CH3)3, CH2-O-CH3.

[0073] According to a further embodiment of the compound of formula I, R 5 are phenyl, 2-F-phenyl, 4-F-phenyl, 2,4-F2-phenyl, 2-Cl-phenyl, 4-Cl-phenyl, CH2-phenyl, CH2-2-F-phenyl, CH2-4-F-phenyl.

[0074] According to one embodiment of the compound of formula I, R 6is independently selected at each occurrence from halogen, CN, C1-C6 alkyl, C1-C6 halogenalkyl, C2-C6 alkenyl, C2-C6 halogenalkenyl, C2-C6 alkynyl, C2-C6 halogenalkynyl, C1-C6 alkyl-O-C1-C6 alkyl, phenyl, benzyl, and C1-C6 alkyl-O-phenyl; Here, R 6 The phenyl and benzyl moieties of 6a and which groups are, independently of one another, It is selected from halogen, CN, C1-C6 alkyl, C1-C6 halogen alkyl, and O-C1-C6 alkyl.

[0075] According to one embodiment of the compound of formula I, R 6 is independently selected in each occurrence from C1-C6 alkyl (embodiment 6.1), C1-C6 alkyl-O-phenyl (embodiment 6.2), C1-C6 alkyl-O-C1-C6 alkyl (embodiment 6.3), halogen (embodiment 6.4).

[0076] According to a further embodiment of the compound of formula I, R 6 is CH3 or CF3.

[0077] According to a further embodiment of the compound of formula I, R 6 are CH2CH3, CH(CH3)2, CH(CH3)CH2CH3, C(CH3)3, CH2-CH(CH3)2, CH2-C(CH3)3, CH2-CH(CH3)-C(CH3)3, CH2-CH2-C(CH3)3, CH2-O-CH3, CH2-O-(CH3)3, CH2-O-phenyl.

[0078] According to a further embodiment of the compound of formula I, R 5 and R 6 form together with the C atom to which they are attached a C3-C6 cycloalkyl or a 3-6 membered saturated heterocycle containing 1, 2 or 3 heteroatoms from the group consisting of O and S.

[0079] According to a further embodiment of the compound of formula I, R 5 and R 6 forms a C3-C6 cycloalkyl (embodiment 6.5).

[0080] According to a further embodiment of the compound of formula I, R 5 and R 6 forms a 3-6 membered saturated heterocycle containing 1, 2 or 3 heteroatoms selected from the group consisting of O and S.

[0081] According to a further embodiment of the compound of formula I, R 5 and R 6 forms a 3-6 membered saturated heterocycle containing one O (embodiment 6.6).

[0082] R according to the present invention 5 , R 6 Preferred embodiments of R are found in Table P5 below, where each row of P5-1 to P5-18 corresponds to one particular embodiment of the present invention, where P5-1 to P5-18 are also preferred embodiments of the present invention in any combination with each other. 5 and R 6 The attachment point to the carbon atom to which is bonded is marked with a "#" in the drawing.

[0083] [Table 3]

[0084] R 7 is in each case hydrogen, CN, CH2CN, CH(CH3)CN, CH(=O), C(=O)C1-C6 alkyl, C(=O)C2-C6 alkenyl, C(=O)C2-C6 alkynyl, C(=O)C3-C6 cycloalkyl, C(=O)NH-C1-C4 alkyl, C(=O)N-(C1-C4 alkyl) 2、C1-C6 alkyl, O-C1-C6 alkyl, C1-C4 halogen alkyl, C3-C6 cycloalkyl, C3-C6 halogen cycloalkyl, C2-C6 alkenyl, C2-C6 halogen alkenyl, C2-C6 alkynyl, C2-C6 halogen alkynyl, -S(=O)2-R 7a , 5- or 6-membered heteroaryl and aryl; where heteroaryl contains 1, 2 or 3 heteroatoms selected from N, O and S; where the aryl group is unsubstituted or has 1, 2, 3, 4 or 5 substituents selected from the group consisting of CN, halogen, OH, C1-C4 alkyl, C1-C4 halogen alkyl, C1-C4 alkoxy and C1-C4 halogen alkoxy; where R 7a is selected from C1-C6 alkyl, C1-C6 halogen alkyl, C2-C6 alkenyl, C2-C6 halogen alkenyl, C2-C6 alkynyl, C2-C6 halogen alkynyl, phenyl, benzyl, where phenyl and benzyl can be unsubstituted or substituted by halogen, C1-C6 alkyl, C1-C6 halogen alkyl, C2-C6 alkenyl, C2-C6 halogen alkenyl, C2-C6 alkynyl, C2-C6 halogen alkynyl.

[0085] According to one embodiment of the compound of formula I, R 7 is H.

[0086] According to yet another embodiment of formula I, R 7 is Cl, F.

[0087] According to yet another embodiment of formula I, R 7 is CN, CHCN or CH(CH)CN.

[0088] According to a further specific embodiment of formula I, R 7 is CH(=O).

[0089] According to a further specific embodiment of formula I, R 7is OCH3 or OCH2CH3.

[0090] According to a further specific embodiment of formula I, R 7 is C(=O)C1-C6 alkyl, where alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.

[0091] According to a further specific embodiment of formula I, R 7 is C(=O)C2-C6 alkenyl, where alkenyl is CH=CH 2、 CH2CH=CH2.

[0092] According to a further specific embodiment of formula I, R 7 is C(=O)C2-C6 alkynyl, where alkynyl is C≡CH 、 CH2C≡CH.

[0093] According to a further specific embodiment of formula I, R 7 is C(=O)C3-C6 cycloalkyl, where cycloalkyl is cyclopropyl (C3H7) or cyclobutyl (C4H9).

[0094] According to a further specific embodiment of formula I, R 7 is C(=O)NH-C1-C4 alkyl or C(=O)N-(C1-C4 alkyl)2, where alkyl is CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl.

[0095] According to yet another embodiment of formula I, R 7 is C1-C6 alkyl, for example, CH3, C2H5, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, n-pentyl or i-pentyl.

[0096] According to yet another embodiment of formula I, R 7is C1-C6 alkyl, particularly C1-C4 alkyl, such as CH3, C2H5, n-propyl, i-propyl, etc.

[0097] According to yet another embodiment of formula I, R 7 is C1-C6 halogen alkyl, particularly C1-C4 halogen alkyl, such as CF3, CCl3, FCH2, ClCH2, F2CH, Cl2CH, CF3CH2, CCl3CH2 or CF2CHF2.

[0098] According to yet another embodiment of formula I, R 7 is C3-C6 cycloalkyl, particularly cyclopropyl.

[0099] According to yet another embodiment of formula I, R 7 is C3-C6 halogen cycloalkyl. In particular embodiments, R 5b is a fully or partially halogenated cyclopropyl, such as 1-Fcyclopropyl, 1-Clcyclopropyl, 1,1-F2cyclopropyl, 1,1-Cl2cyclopropyl, and the like.

[0100] According to yet a further embodiment of formula I, R 7 is C2-C6 alkenyl, particularly C2-C4 alkenyl, such as CH=CH2, C(CH3)=CH2, CH2CH=CH2, etc.

[0101] According to a more specific embodiment of formula I, R 7 is C2-C6 halogen alkenyl, particularly C2-C4 halogen alkenyl, more particularly C2-C3 halogen alkenyl, such as CH=CHF, CH=CHCl, CH=CF2, CH=CCl2, CH2CH=CHF, CH2CH=CHCl, CH2CH=CF2, CH2CH=CCl2, CF2CH=CF2, CCl2CH=CCl2, CF2CF=CF2, CCl2CCl=CCl2, etc.

[0102] According to yet a further embodiment of formula I, R 7is C2-C6 alkynyl or C2-C6 halogen alkynyl, particularly C2-C4 alkynyl or C2-C4 halogen alkynyl, such as C≡CH, CH2C≡CH, etc.

[0103] According to yet a further embodiment of formula I, R 7 is -S(=O)2-R 7a where R 7a is preferably C1 to C6 alkyl, in particular C1 to C4 alkyl, such as CH3, C2H5, n-propyl, i-propyl, etc.

[0104] According to yet another embodiment of formula I, R 7 is aryl, in particular phenyl, where the aryl or phenyl moiety is in each case unsubstituted or bears identical or different groups R 5b and which groups are selected, independently of one another, from halogen, C1-C2 alkyl, C1-C2 alkoxy, C1-C2 halogen alkyl and C1-C2 halogen alkoxy, in particular F, Cl, Br, CH3, OCH3, CF3 and OCF3. According to one embodiment, R 5 is unsubstituted phenyl. According to another embodiment, R 5 is phenyl substituted by 1, 2 or 3, especially 1, halogen selected from F, Cl and Br, more especially selected from F and Cl.

[0105] According to yet another embodiment of formula I, R 7is a 5-membered heteroaryl, such as pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1,2,4-triazolyl-1-yl, 1,2,4-triazol-3-yl These include 1,2,4-triazol-5-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, and 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl.

[0106] According to yet another embodiment of formula I, R 7 is 6-membered heteroaryl, such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl, and 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl.

[0107] According to yet another embodiment of formula I, R 7 is independently selected at each occurrence from H, halogen, OH, CN, C1-C6 alkyl, C1-C6 halogenalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 halogenalkoxy, C3-C6 alkenyloxy, C3-C6 alkynyloxy, and C3-C6 cycloalkyl, where R 5 The acyclic moieties of are unsubstituted or substituted with identical or different groups R as defined, preferably as defined herein. 5a where R5 The carbocyclic, phenyl and heteroaryl moieties of are unsubstituted or substituted with identical or different groups R as defined, preferably as defined herein. 5b has been replaced with.

[0108] R according to the present invention 7 Particularly preferred embodiments of are found in Table P7 below, where each row of rows P7-1 to P7-32 corresponds to one particular embodiment of the invention, where P7-1 to P7-32 are also preferred embodiments of the invention in any combination with each other. 7 The attachment point to the carbon atom to which is bonded is marked with a "#" in the drawing.

[0109] [Table 4]

[0110] According to one embodiment of the compound of formula I, X is independently selected at each occurrence from halogen (embodiment X.1), CN, C1-C6 alkyl (embodiment X.2), C1-C6 halogen alkyl (embodiment X.3), O-C1-C6 alkyl (embodiment X.4), O-C1-C6 halogen alkyl (embodiment X.5).

[0111] According to one embodiment of the compound of formula I, X, at each occurrence, is independently selected from halogen, O-C1-C6 alkyl.

[0112] According to one embodiment of the compound of formula I, X, at each occurrence, is independently selected from F or Cl.

[0113] According to one embodiment of the compound of formula I, X is a C3-C6 cycloalkyl.

[0114] According to one embodiment of the compound of formula I, n is 0.

[0115] According to one embodiment of the compound of formula I, n is 1.

[0116] According to one embodiment of the compound of formula I, n is 2.

[0117] According to one embodiment, Xn is: [ka] and X is selected from F, Cl, I, CH3, cyclopropyl, CH=CH2, C≡CH, OCH3, OCHF2, CF3, CHF2, CH2CH3, CN.

[0118] According to one embodiment, Xn is: [ka] and X is selected from F, Cl, I, CH3, cyclopropyl, CH=CH2, C≡CH, OCH3, OCHF2, CF3, CHF2, CH2CH3, CN.

[0119] According to one embodiment, Xn is: [ka] and X is selected from F, Cl, I, CH3, cyclopropyl, CH=CH2, C≡CH, OCH3, OCHF2, CF3, CHF2, CH2CH3, CN.

[0120] According to one embodiment, Xn is: [ka] and X is selected from F, Cl, I, CH3, cyclopropyl, CH=CH2, C≡CH, OCH3, OCHF2, CF3, CHF2, CH2CH3, CN.

[0121] According to one embodiment, Xn is: [ka] and X is selected from F, Cl, I, CH3, cyclopropyl, CH=CH2, C≡CH, OCH3, OCHF2, CF3, CHF2, CH2CH3, CN.

[0122] In a further embodiment, the present invention relates to a compound of formula I as defined below, wherein the variable R 2 , R 3 and X (represented by embodiments X.1 to X.6), relating to embodiments E.1 to E.275 listed in Table E, which for each n represent preferred combinations of the embodiments defined above. [ka]

[0123] [Table 5]

[0124] [Table 6]

[0125] [Table 7]

[0126] [Table 8]

[0127] [Table 9]

[0128] [Table 10]

[0129] [Table 11]

[0130] [Table 12]

[0131] In a further aspect, the present invention provides a compound comprising R 5 is represented in embodiment 5.1, and R 6 This relates to embodiments E.1 to E.280 listed in Table E, which is represented as embodiment 6.1.

[0132] In a further aspect, the present invention provides a compound comprising R 5 is represented in embodiment 5.2, and R 6 This relates to embodiments E.1 to E.280 listed in Table E, which is represented as embodiment 6.1.

[0133] In a further aspect, the present invention provides a compound comprising R 5 is represented in embodiment 5.3, and R 6 This relates to embodiments E.1 to E.280 listed in Table E, which is represented as embodiment 6.1.

[0134] In a further aspect, the present invention provides a compound comprising R 5 is represented in embodiment 5.4, and R 6 This relates to embodiments E.1 to E.280 listed in Table E, which is represented as embodiment 6.1.

[0135] In a further aspect, the present invention provides a compound comprising R 5 is represented in embodiment 5.5, and R 6 This relates to embodiments E.1 to E.280 listed in Table E, which is represented as embodiment 6.1.

[0136] In a further aspect, the present invention provides a compound comprising R 5 is represented in embodiment 5.1, and R 6 This relates to embodiments E.1 to E.280 listed in Table E, which is represented as embodiment 6.2.

[0137] In a further aspect, the present invention provides a compound comprising R 5is represented in embodiment 5.2, and R 6 This relates to embodiments E.1 to E.280 listed in Table E, which is represented as embodiment 6.2.

[0138] In a further aspect, the present invention provides a compound comprising R 5 is represented in embodiment 5.3, and R 6 This relates to embodiments E.1 to E.280 listed in Table E, which is represented as embodiment 6.2.

[0139] In a further aspect, the present invention provides a compound comprising R 5 is represented in embodiment 5.4, and R 6 This relates to embodiments E.1 to E.280 listed in Table E, which is represented as embodiment 6.2.

[0140] In a further aspect, the present invention provides a compound comprising R 5 is represented in embodiment 5.5, and R 6 This relates to embodiments E.1 to E.280 listed in Table E, which is represented as embodiment 6.2.

[0141] In a further aspect, the present invention provides a compound comprising R 5 is represented in embodiment 5.1, and R 6 This relates to embodiments E.1 to E.280 listed in Table E, which is represented as embodiment 6.3.

[0142] In a further aspect, the present invention provides a compound comprising R 5 is represented in embodiment 5.2, and R 6 This relates to embodiments E.1 to E.280 listed in Table E, which is represented as embodiment 6.3.

[0143] In a further aspect, the present invention provides a compound comprising R 5 is represented in embodiment 5.3, and R 6 This relates to embodiments E.1 to E.280 listed in Table E, which is represented as embodiment 6.3.

[0144] In a further aspect, the present invention provides a compound comprising R 5 is represented in embodiment 5.4, and R 6This relates to embodiments E.1 to E.280 listed in Table E, which is represented as embodiment 6.3.

[0145] In a further aspect, the present invention provides a compound comprising R 5 is represented in embodiment 5.5, and R 6 This relates to embodiments E.1 to E.280 listed in Table E, which is represented as embodiment 6.3.

[0146] In a further aspect, the present invention provides a compound comprising R 5 is represented in embodiment 5.1, and R 6 This relates to embodiments E.1 to E.280 listed in Table E, which is represented by embodiment 6.4.

[0147] In a further aspect, the present invention provides a compound comprising R 5 is represented in embodiment 5.2, and R 6 This relates to embodiments E.1 to E.280 listed in Table E, which is represented by embodiment 6.4.

[0148] In a further aspect, the present invention provides a compound comprising R 5 is represented in embodiment 5.3, and R 6 This relates to embodiments E.1 to E.280 listed in Table E, which is represented by embodiment 6.4.

[0149] In a further aspect, the present invention provides a compound comprising R 5 is represented in embodiment 5.4, and R 6 This relates to embodiments E.1 to E.280 listed in Table E, which is represented by embodiment 6.4.

[0150] In a further aspect, the present invention provides a compound comprising R 5 is represented in embodiment 5.5, and R 6 This relates to embodiments E.1 to E.280 listed in Table E, which is represented by embodiment 6.4.

[0151] In a further aspect, the present invention provides a compound comprising R 5 and R 6 This relates to embodiments E.1 to E.280 listed in Table E, which is represented by embodiment 6.5.

[0152] In a further aspect, the present invention provides a compound comprising R 5 and R 6 This relates to embodiments E.1 to E.280 listed in Table E, which is represented as embodiment 6.6.

[0153] Preferred embodiments of the present invention are the following compounds IA-1, IA-2, IA-3, and IA-4, in which the substituent R 5 , R 6 and Xn are independently as defined above or preferably as defined herein: [ka]

[0154] In particular, in view of their use, according to one embodiment, the compounds IA-1, IA-2, IA-3, IA-4 are preferred; they are summarized in Tables 1a to 7a. Each of the groups mentioned for the substituents in the tables is furthermore itself a particularly preferred embodiment of the substituent in question, independently of the combination in which it is mentioned.

[0155] Table 1a Xn is H and R for each individual compound 5 , R 6 and R 7 Compounds of the formulae IA-1, IA-2, IA-3, IA-4, the meaning of which for the combinations corresponds in each case to one line of table B (compounds IA-1.1aB-1 to IA-1.1aB-100, IA-2.1aB-1 to IA-2.1aB-100, IA-3.1aB-1 to IA-3.1aB-100, IA-4.1aB-1 to IA-4.1aB-100).

[0156] Table 2a Xn is 8-F and R for each individual compound 5 , R 6 and R 7Compounds of the formulae IA-1, IA-2, IA-3, IA-4, the meaning of which for the combinations corresponds in each case to one line of table B (compounds IA-1.2aB-1 to IA-1.2aB-100, IA-2.2aB-1 to IA-2.2aB-100, IA-3.2aB-1 to IA-3.2aB-100, IA-4.2aB-1 to IA-4.2aB-100).

[0157] Table 3a Xn is 8-Cl and R for each individual compound 5 , R 6 and R 7 Compounds of the formulae IA-1, IA-2, IA-3, IA-4, whose meanings for the combinations correspond in each case to one line of table B (compounds IA-1.3aB-1 to IA-1.3aB-100, IA-2.3aB-1 to IA-2.3aB-100, IA-3.3aB-1 to IA-3.3aB-100, IA-4.3aB-1 to IA-4.3aB-100).

[0158] Table 4a Xn is 8-CH3 and R for each individual compound 5 , R 6 and R 7 Compounds of the formulae IA-1, IA-2, IA-3 and IA-4, the meanings of which for the combinations correspond in each case to one line of table B (compounds A-1.4aB-1 to IA-1.4aB-100, IA-2.4aB-1 to IA-2.4aB-100, IA-3.4aB-1 to IA-3.4aB-100, IA-4.4aB-1 to IA-4.4aB-100).

[0159] Table 5a Xn is 7,8-F2 and R for each individual compound 5 , R 6 and R 7Compounds of the formulae IA-1, IA-2, IA-3, IA-4, the meaning of which for the combinations corresponds in each case to one line of table B (compounds IA-1.5aB-1 to IA-1.5aB-100, IA-2.5aB-1 to IA-2.5aB-100, IA-3.5aB-1 to IA-3.5aB-100, IA-4.5aB-1 to IA-4.5aB-100).

[0160] Table 6a Xn is 8-OCH3 and R for each individual compound 5 , R 6 and R 7 Compounds of the formulae IA-1, IA-2, IA-3, IA-4, the meanings of which for the combinations correspond in each case to one line of table B (compounds IA-1.6aB-1 to IA-1.6aB-100, IA-2.6aB-1 to IA-2.6aB-100, IA-3.6aB-1 to IA-3.6aB-100, IA-4.6aB-1 to IA-45.6aB-100)

[0161] Table 7a Xn is 7-F-8-OCH3 and R for each individual compound 5 , R 6 and R 7 Compounds of the formulae IA-1, IA-2, IA-3, IA-4, the meaning of which for the combinations corresponds in each case to one line of table B (compounds IA-1.7aB-1 to IA-1.7aB-100, IA-2.7aB-1 to IA-2.7aB-100, IA-3.7aB-1 to IA-3.7aB-100, IA-4.7aB-1 to IA-4.7aB-100).

[0162] [Table 13]

[0163] [Table 14]

[0164] [Table 15]

[0165] [Table 16]

[0166] The compounds of the present invention can be prepared as shown in the following schemes, in which, unless otherwise indicated, the definition of each variable is as defined above for the compound of formula I. The compounds of formula I can be prepared according to or analogous to the methods described in the prior art. The synthesis utilizes starting materials that are either commercially available or can be prepared according to conventional procedures starting from readily available compounds.

[0167] For example, the formation of compound I from a compound of formula 2 is suitably carried out by alkylation or acylation in the presence of a base such as potassium or sodium lower alkoxides or hydrides. Di-lower alkyl sulfates can also be used to effect the alkylation or acylation, as described in U.S. Pat. No. 3,625,959.

[0168] Cyclic compounds of formula 2 can be prepared from ketoamine compounds 1 by reaction with ketones or aldehydes of formula 1a in the presence of ammonium acetate. In some cases, the presence of an acid such as p-toluenesulfonic acid (p-TsOH), pyridinium p-toluenesulfonate, sulfuric acid, or acetic acid improves the yield (for examples, see, for example, Chemistry Select (2018), 3(32), 9388-9392 and Organic & Biomolecular Chemistry (2003), 1(2), 367-372). [ka]

[0169] Compounds of 1 are either commercially available or can be accessed by oxidation of amino alcohols 7 using, for example, manganese dioxide, as described in Inorganica Chimica Acta (2012), 382, ​​72-78, WO 2000038618, CN 107879989 A, Chinese Science Bulletin (2010), 55(25), 2817-2819, following the general route outlined in Scheme 1 below.

[0170] Compounds of formula 7 can be accessed by catalytic hydrogenation of the respective nitroalcohols 6 using RANEY® nickel, as described in WO 2000038618, Inorganica Chimica Acta (2012), 382, ​​72-78.

[0171] 2-Nitroalcohols 6 can be prepared from 4 by phenylmagnesium bromide-mediated iodine-magnesium exchange at the ortho position to NO2 as described by Knochel and co-workers (Angew. Chem., Int. Ed., 2002, 41, 1610) and subsequent addition to commercially available benzaldehyde derivatives 5. Scheme 1: [ka]

[0172] R 7Compounds of formula I, where is alkoxy, can be prepared from 6 by the following synthetic route, characterized by selective catalytic hydrogenation of nitroalcohols 6 to the corresponding N-arylhydroxylamines 8 using passivated RANEY® nickel treated with a combined aqueous ammonia and DMSO liquid as described in RSC Advances (2020), 28585-28594, or using platinum on carbon (Type F 103 RS / W from Degussa) as described in Indian Patent No. 1996CH00112. [ka]

[0173] Compounds of formula 9 can be prepared by oxidation of hydroxylamine alcohols 8 using, for example, manganese dioxide, as described in Inorganica Chimica Acta (2012), 382, ​​72-78 and WO2000038618.

[0174] The protected hydroxylamine 10 can be prepared by methods well known in the literature for amino protecting groups such as those discussed in Theodora W. Greene's book "Protective Groups in Organic Synthesis", such as N-Boc using di-tert.butyl dicarbonate in a suitable solvent such as DMSO.

[0175] Compound 10 can be alkylated by deprotonating the hydroxylamine using a standard base such as LDA, NaH, or NaHMDS, followed by the addition of an alkylating agent with a suitable leaving group such as a halide, mesylate, or triflate in a suitable solvent to provide compound 11 (see, for example, Chinese Patent No. 207973751 for a previous example).

[0176] The N-Boc protecting group can be removed by a number of methods well known in the literature, such as TFA in methylene chloride, to give compound 12 (see, for example, WO 2000038618 for examples).

[0177] Finally, R 7 Compound I, in which is alkoxy, can be prepared from 12 by treatment with NHOAc as described in Chemistry Select (2018), 3(32), 9388-9392 and Organic & Biomolecular Chemistry (2003), 1(2), 367-372.

[0178] Compound I and its compositions are suitable as fungicides that are effective against a wide range of plant pathogenic fungi, including soil-borne fungi, in particular those from the classes Plasmodiophoromycetes, Peronosporomycetes (synonymous with Oomycetes), Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, and Deuteromycetes (synonymous with Fungi imperfecti).They can be used in crop protection as foliar fungicides, seed dressing fungicides, and soil fungicides.

[0179] The compounds I and compositions thereof are preferably suitable for use in various cultivated plants, such as cereals, for example wheat, rye, barley, triticale, oats or rice; beets, for example sugar beet or fodder beet; fruits, for example pome fruits (apples, pears, etc.), stone fruits (for example plums, peaches, almonds, cherries) or soft fruits, also called berries (strawberries, raspberries, blackberries, currants, etc.); legumes, for example lentils, peas, alfalfa or soybeans; oil plants, for example rapeseed, mustard, olives, sunflowers, coconuts, cocoa beans, castor oil plants, oil palm, peanuts or soybeans; cucurbits, for example pumpkin, cucumber or melon; fibre plants, for example cotton, flax, cannabis or parsley; citrus fruits, for example oranges. , lemon, grapefruit or mandarin; vegetables such as spinach, lettuce, asparagus, cabbage, carrot, onion, tomato, potato, melons or paprika; lauraceae plants such as avocado, cinnamon or camphor; energy and raw material plants such as corn, soybean, rapeseed, sugarcane or oil palm; corn; tobacco; nuts; coffee; tea; bananas; grapes (table grapes and grape juice grapes); hops; turfgrass; cypress (also called stevia); natural rubber plants; or ornamental and forest plants such as flowers, shrubs, broadleaf trees or evergreen trees (conifers, eucalyptus, etc.); on plant propagation material such as seeds; and on crop material of these plants.

[0180] More preferably, the compounds I and compositions thereof, respectively, are used to control fungi on agricultural crops, such as potato, sugar beet, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybean, rapeseed, legumes, sunflower, coffee or sugarcane; fruits; grapes; ornamental plants; or vegetables, such as cucumber, tomato, bean or pumpkin.

[0181] The term "plant propagation material" is understood to refer to all reproductive parts of plants, such as seeds, as well as plant material capable of growth, such as cuttings and tubers (e.g., potatoes), that can be used for the propagation of plants. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts, and other parts of plants, including seedlings and young plants that are transplanted after germination or emergence from the soil.

[0182] Preferably, the treatment of plant propagation material with compound I and compositions thereof, respectively, is used to control fungi on cereals, such as wheat, rye, barley and oats; rice, corn, cotton and soybean.

[0183] According to the present invention, all of the above mentioned cultivated plants are understood to include all species, subspecies, varieties, cultivars and / or hybrids belonging to each cultivated plant, including, but not limited to, cereals such as wheat and barley, and winter and spring cultivars in rapeseed, e.g. winter wheat, spring wheat, winter barley, etc.

[0184] Maize is also known as Indian corn or maize (Zea mays), which includes all types of maize such as fodder maize and sweet corn. According to the present invention, all maize or corn subspecies and / or varieties are included, in particular flower corn (Zea mays var. amylacea), popcorn (Zea mays var. everta), dent corn (Zea mays var. indentata), flint corn (Zea mays var. indurata), sweet corn (Zea mays var. saccharata and var. rugosa), waxy corn (Zea mays var. ceratina), amylomaize (high amylose Zea mays varieties), pod corn or wild maize (Zea mays var. tunicata) and striped corn (Zea mays var. japonica).

[0185] Most soybean varieties are classified into indeterminate and determinate growth habits, although the wild ancestor of soybean, Glycine soja, is indeterminate (PNAS 2010,107(19)8563-856). Indeterminate growth habits (maturity groups, MG 00 to MG 4.9) are characterized by the continuation of vegetative growth after flowering begins, whereas determinate soybean varieties (MG 5 to MG 8) are characterized by the termination of most of their vegetative growth at the onset of flowering. According to the invention, all soybean cultivars or varieties are included, in particular indeterminate and determinate cultivars or varieties.

[0186] The term "cultivated plants" is understood to include plants that have been modified by mutagenesis or genetic engineering to confer new traits to the plant or to modify traits already present. Mutagenesis includes random mutagenesis using X-rays or mutagenic chemicals, but also targeted mutagenesis to generate mutations at specific loci in the plant genome. Targeted mutagenesis often uses oligonucleotides or proteins such as CRISPR / Cas, zinc finger nucleases, TALENs or meganucleases. Genetic engineering usually uses recombinant DNA techniques to generate modifications in the plant genome that are not readily obtainable by breeding, mutagenesis or natural recombination under natural circumstances. Typically, one or more genes are integrated into the genome of the plant to add or improve or modify traits. These integrated genes are also referred to as transgenes, while plants containing such transgenes are referred to as transgenic plants. The process of plant transformation usually involves several transformation events that differ in the genomic loci at which the transgenes are integrated. A plant containing a particular transgene at a particular genomic locus is usually said to contain a particular "event" and is referred to by the name of the particular event. Traits that have been introduced or modified in the plant include herbicide tolerance, insect resistance, high yield and tolerance to abiotic conditions such as drought.

[0187] Herbicide tolerance is produced by using mutagenesis and genetic engineering. Plants that have been made tolerant to acetolactate synthase (ALS) inhibitor herbicides by mutagenesis and breeding are available, for example, under the name Clearfield®. Herbicide tolerance to glyphosate, glufosinate, 2,4-D, dicamba, oxynil herbicides such as bromoxynil and ioxynil, sulfonylurea herbicides, ALS inhibitors, and 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors such as isoxaflutole and mesotrione is produced by using transgenes.

[0188] Transgenes conferring herbicide tolerance traits include: glyphosate tolerance conferring: cp4 epsps, epsps grg23ace5, mepsps, 2mepsps, gat4601, gat4621, goxv247; glufosinate tolerance conferring: pat and bar; 2,4-D tolerance conferring: aad-1, aad-12; dicamba tolerance conferring: dmo; oxynil herbicide tolerance conferring: bxn; sulfonylurea herbicide tolerance conferring: zm-hra, csr1-2, gm-hra, S4-HrA, ALS inhibitor tolerance conferring: csr1-2; and HPPD inhibitor tolerance conferring: hppdPF, W336, avhppd-03.

[0189] Transgenic corn events containing herbicide tolerance genes include, but are not limited to, DAS40278, MON801, MON802, MON809, MON810, MON832, MON87411, MON87419, MON87427, MON88017, MON89034, NK603, GA21, MZHG0JG, HCEM485, VCO-Φ1981-5, 676, 678, 680, 33121, 4114, 59122, 98140, Bt10, Bt176, CBH-351, DBT418, DLL25, MS3, MS6, MZIR098, T25, TC1507, and TC6275. Transgenic soybean events containing herbicide tolerance genes include, but are not limited to, GTS40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21, A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS-81419-2, GU262, SYHTΦH2, W62, W98, FG72, and CV127. Transgenic cotton events containing herbicide tolerance genes include, but are not limited to, 19-51a, 31707, 42317, 81910, 281-24-236, 3006-210-23, BXN10211, BXN10215, BXN10222, BXN10224, MON1445, MON1698, MON88701, MON88913, GHB119, GHB614, LLCotton25, T303-3 and T304-40. Transgenic canola events containing herbicide tolerance genes include, but are not limited to, MON88302, HCR-1, HCN10, HCN28, HCN92, MS1, MS8, PHY14, PHY23, PHY35, PHY36, RF1, RF2 and RF3.

[0190] The transgenes conferring insect resistance are preferably Bacillus spp. toxin genes such as cry1A, cry1Ab, cry1Ab-Ac, cry1Ac, cry1A.105, cry1F, cry1Fa2, cry2Ab2, cry2Ae, mcry3A, ecry3.1Ab, cry3Bb1, cry34Ab1, cry35Ab1, cry9C, vip3A(a), vip3Aa20, and synthetic variants thereof. In addition, transgenes of plant origin can be used, such as genes encoding protease inhibitors, such as CpTI and pinII. A further approach is to produce double-stranded RNA in plants using transgenes such as dvsnf7.

[0191] Transgenic corn events containing genes for insecticidal proteins or double-stranded RNA include, but are not limited to, Bt10, Bt11, Bt176, MON801, MON802, MON809, MON810, MON863, MON87411, MON88017, MON89034, 33121, 4114, 5307, 59122, TC1507, TC6275, CBH-351, MIR162, DBT418, and MZIR098. Transgenic soybean events containing genes for insecticidal proteins include, but are not limited to, MON87701, MON87751, and DAS-81419. Transgenic cotton events containing genes for insecticidal proteins include, but are not limited to, SGK321, MON531, MON757, MON1076, MON15985, 31707, 31803, 31807, 31808, 42317, BNLA-601, Event1, COT67B, COT102, T303-3, T304-40, GFMCry1A, GK12, MLS9124, 281-24-236, 3006-210-23, GHB119, and SGK321.

[0192] Cultivated plants with increased yields have been produced by using the transgenes athb17 (eg, maize event MON87403) or bbx32 (eg, soybean event MON87712).

[0193] Cultivated plants with altered oil yields have been produced using the transgenes gm-fad2-1, Pj.D6D, Nc.Fad3, fad2-1A and fatb1-A (e.g., soybean events 260-05, MON87705 and MON87769).

[0194] Tolerance to abiotic conditions, such as drought, has been produced by using the transgenes cspB (maize event MON87460) and Hahb-4 (soybean event IND-ΦΦ41Φ-5).

[0195] Traits are often combined by combining genes in a transformation event or by combining different events during the breeding process, resulting in cultivated plants with stacked traits. Preferred combinations of traits are combinations of herbicide resistance traits for different groups of herbicides, insect resistance for different types of insects, especially resistance to lepidopteran and coleopteran insects, herbicide resistance and resistance to one or several insects, herbicide resistance and increased yield, and herbicide resistance and resistance to abiotic conditions.

[0196] Plants containing single or stacked traits and the genes and events that confer these traits are well known in the art. For example, detailed information on mutant or integrated genes and respective events is available on the website of the organization "International Service for the Acquisition of Agri-biotech Applications (ISAAA)" (http: / / www.isaaa.org / gmapprovaldatabase) and the website of the organization "Center for Environmental Risk Assessment (CERA)" (http: / / cera-gmc.org / GMCropDatabase). For further information on specific events and how to detect them, see WO 01 / 031042, WO 01 / 041558, WO 01 / 041558, WO 02 / 036831, WO 11 / 153186, WO 13 / 003558 for canola events MS1, MS8, RF3, GT73, MON88302, KK179;Regarding cotton events MON1445, MON15985, MON531 (MON15985), LLCotton25, MON88913, COT102, 281-24-236, 3006-210-23, COT67B, GHB614, T304-40, GHB119, MON88701, and 81910, International Publication No. 02 / 034946, International Publication No. 02 / 100163, International Publication No. 02 / 100163, and International Publication No. 03 / 013224 , WO 04 / 072235, WO 04 / 039986, WO 05 / 103266, WO 05 / 103266, WO 06 / 128573, WO 07 / 017186, WO 08 / 122406, WO 08 / 151780, WO 12 / 134808, WO 13 / 112527;Regarding corn events GA21, MON810, DLL25, TC1507, MON863, MIR604, LY038, MON88017, 3272, 59122, NK603, MIR162, MON89034, 98140, 32138, MON87460, 5307, 4114, MON87427, DAS40278, MON87411, 33121, MON87403, and MON87419, see WO 98 / 044140 and U.S. Patent Application Publication No. 02 / 102582. , U.S. Patent Application Publication No. 03 / 126634, WO 04 / 099447, WO 04 / 011601, WO 05 / 103301, WO 05 / 061720, WO 05 / 059103, WO 06 / 098952, WO 06 / 039376, U.S. Patent Application Publication No. 2007 / 292854, WO 07 / 142840, WO Publication No. WO 07 / 140256, WO 08 / 112019, WO 09 / 103049, WO 09 / 111263, WO 10 / 077816, WO 11 / 084621, WO 11 / 062904, WO 11 / 022469, WO 13 / 169923, WO 14 / 116854, WO 15 / 0 WO 15 / 142571; WO 14 / 178910, WO 14 / 178913, WO 14 / 178941, WO 14 / 179276, WO 16 / 183445, WO 17 / 062831, WO 17 / 062825 for potato events E12, F10, J3, J55, V11, X17, Y9;For rice events LLRICE06, LLRICE601, and LLRICE62, WO 00 / 026345, WO 00 / 026356, and WO 00 / 026345; and for soybean events H7-1, MON89788, A2704-12, A5547-127, DP305423, DP356043, and M Regarding ON87701, MON87769, CV127, MON87705, DAS68416-4, MON87708, MON87712, SYHT0H2, DAS81419, DAS81419×DAS44406-6, and MON87751, International Publication No. 04 / 074492, International Publication No. 06 / 130436, International Publication No. 06 / 10 8674, WO 06 / 108675, WO 08 / 054747, WO 08 / 002872, WO 09 / 064652, WO 09 / 102873, WO 10 / 080829, WO 10 / 037016, WO 11 / 066384, WO 11 / 034704, WO 12 / 051199, WO 12 / 082548, WO 13 / 016527, WO 13 / 016516, WO 14 / 201235;

[0197] The use of compound I and its compositions, respectively, on cultivated plants can result in effects that are specific to the cultivated plants that contain a particular transgene or event. These effects can include changes in growth behavior or changes in resistance to biotic or abiotic stress factors. Such effects can include, in particular, increased yield, resistance or improved resistance to insect, nematode, fungal, bacterial, mycoplasma, viral or viroid pathogens, and early growth, early or delayed maturation, low or high temperature resistance, and changes in amino acid or fatty acid spectrum or content.

[0198] The compounds I and their compositions, respectively, are particularly suitable for controlling the etiology of the following plant diseases:

[0199] Albugo species (white rust) on ornamental plants, vegetables (e.g. A. candida) and sunflower (e.g. A. tragopogonis); vegetables (e.g. A. dauci or A. porri), rapeseed (A. brassicicola or A. brassicae) Alternaria species (Alternaria leaf spot) on cereals and vegetables, e.g. A. tritici (anthracnose) on wheat and A. hordei (barley), sugar beet (A. brassicae), sugar beet (A. tenuis), fruits (e.g. A. grandis), rice, soybean, potato and tomato (e.g. A. solani, A. grandis or A. alternata), tomato (e.g. A. solani or A. alternata) and wheat (e.g. A. triticina); Aphanomyces species on sugar beet and vegetables; Ascochyta species on cereals and vegetables, e.g. A. tritici (anthracnose) on wheat and A. hordei on barley; eyespot (Aureobasidium) on maize. zeae (synonym: Kapatiella zeae); Bipolaris spp. and Drechslera spp. (teleomorph: Cochliobolus spp.) on maize, e.g. brown spot (D. maydis) or black spot (B. zeicola), e.g. spot blotch (B. sorokiniana) on cereals and B. oryzae (B. zeicola), e.g. rice and turfgrass.oryzae; Blumeria (formerly Erysiphe) graminis (powdery mildew) on cereals (e.g. on wheat or barley); Botrytis cinerea (teleomorph: Botryotinia fuckeliana: grey mold) on fruits and berries (e.g. strawberry), vegetables (e.g. lettuce, carrot, celery and cabbage); B. squamosa or grey rot (B. allii) on onion, rapeseed, ornamentals (e.g. B eliptica), grapes, forest plants and wheat; Bremia lactucae on lettuce lactucae (downy mildew); Ceratocystis spp. (syn. Ophiostoma) (root rot or dieback) on deciduous and evergreen trees, e.g. C. ulmi (Dutch elm disease) on elms; Cercospora spp. (Cercospora spot) on maize (e.g. gray spot: C. zeae-maydis), rice, sugar beet (e.g. C. beticola), sugar cane, vegetables, coffee, soybean (e.g. C. sojina or C. kikuchii) and rice; Cladobotryum spp. (syn. Dactylium) on mushrooms (e.g. C. mycophilum). (formerly synonymous with Dactylium dendroide, teleomorphs: Nectria albertinii, Nectria rosella, Hypomyces rosellus); Cladosporium species on tomato (e.g. C. fulvum: leaf mold) and cereals, e.g. C. herbarum (black spot) on wheat; Claviceps purpurea on cereals. purpurea (ergot); Cochliobolus (anamorph: Helminthosporium in Bipolaris) species on corn (C. carbonum), cereals (e.g., C. sativus, anamorph: B. sorokiniana) and rice (e.g., C. miyabeanus, anamorph: H. oryzae) (spot disease); cotton (e.g., C. gossypii), corn (e.g., C. graminicola: anthracnose root rot), soft fruits, potatoes (e.g., C. coccodes: black spot), legumes (e.g., C. Colletotrichum (teleomorph: Glomerella) species (anthracnose) on soybeans (e.g. C. lindemuthianum), soybeans (e.g. C. truncatum or C. gleosporioides), vegetables (e.g. C. lagenarium or C. capsici), fruits (e.g. C. acutatum), coffee (e.g. C. coffeeum or C. kahawae) and C. gleosporioides on various crops; Corticium species, e.g. C. sasakii on rice.sasakii (sheath blight); Corynespora cassiicola (spot disease) on soybean, cotton and ornamentals; Cycloconium species, e.g. C. oleaginum on olive trees; fruit trees, grapes (e.g. C. liriodendri, teleomorph: Neonectria liriodendri, teleomorph: Neonectria liriodendri (black leg disease) and Cylindrocarpon species on ornamental plants (e.g. fruit canker disease or young grapevine decline, teleomorph: Nectria or Neonectria); Dematophora (teleomorph: Roselinia) and necatrix (root and stem rot disease) on soybean; Diaporthe species on soybean, e.g. D. phaseolorum (seedling damping off); (synonymous with Helminthosporium, teleomorph Drechslera (synonym: Helminthosporium, teleomorph: Pyrenophora) species on maize, cereals such as barley (e.g. D. teres, net blotch), and wheat (e.g. D. tritici-repentis, yellow spot), rice and turfgrass; Formitiporia (synonym: Phellinus) punctata, F. mediterranea, Phaeomoniella chlamydospora Esca disease (canker, apoplexy) on grapes, caused by Phaeoacremonium chlamydospora (formerly Phaeoacremonium chlamydosporum), Phaeoacremonium aleophilum and / or Botryosphaeria obtusa; E.Elsinoe species on plants (E. pyri), soft fruits (E. veneta: anthracnose) and grapes (E. ampelina: anthracnose); Entyloma oryzae (leaf mildew) on rice; Epicoccum species (black mold) on wheat; Erysiphe species (powdery mildew) on sugar beet (E. betae), vegetables (e.g. E. pisi), e.g. cucurbits (e.g. E. cichoracearum), cabbage, rapeseed (e.g. E. cruciferarum); Eutypa rata species (powdery mildew) on fruit trees, grapes and ornamental trees. lata (Eutipa canker or blight, anamorphs: Cytosporina lata, synonymous with Libertella blepharis); Exserohilum (synonymous with Helminthosporium) species on maize; Fusarium (teleomorph: Gibberella) species on various plants (damage, root or stem rot), such as F. graminearum or F. culmorum (root rot, scab or red mold) on cereals (e.g. wheat or barley), F. oxysporum on tomato, rum, F. solani (synonymous with f. sp. glycines, now F. virguliforme) and F. tucumaniae and F. brasiliense causing sudden death syndrome on soybean, respectively, and F. verticillioides on maize; Gaeumannomyces graminis (damaging disease) on cereals (e.g. wheat or barley) and maize; G. fujikuroi (damaging disease) on cereals (e.g. G. zeae) and rice (e.g. G.fujikuroi;Gibberella spp. on bakanae disease;Glomerella cingulata on grapes, pome fruits and other plants and G. gossypii on cotton;Grain stain complex on rice;Guignardia bidwellii (black rot) on grapes;Gymnosporangium spp. on roses and junipers, e.g. G. sabinae (rust) on pears;Helminthosporium spp. (synonym: Drechslera, teleomorph: Cochliobolus) on maize, cereals, potato and rice;. Hemileia species, such as H. vastatrix (coffee leaf rust) on coffee; Isariopsis clavispora (synonym Cladosporium vitis) on grapes; Macrophomina phaseolina (synonym phaseoli) on soybean and cotton (root and stem rot); Microdochium (synonym Fusarium) nivale (pink snow mold) on cereals (e.g. wheat or barley); Microsphaera diffusa (pink snow mold) on soybeans. diffusa (powdery mildew); Monilinia species, e.g. M. laxa, M. fructicola and M. fructigena (synonymous with Monilia: flower and branch blight, brown rot) on stone fruits and other Rosaceae; Mycosphaerella species, e.g. M. graminicola on wheat (anamorph: Zymoseptoria tritici, formerly Septoria tritici: Septoria leaf spot) or M. fijiensis on banana (Pseudocercospora fijiensis (synonymous with black sigatoka disease) and M. musicola, M. arachidicola (synonymous with M. arachidis or Cercospora arachidis) on peanut, M. berkeleyi, M. pisi on pea and M. brassiciola on cruciferous plants; cabbage (e.g. P. brassicae), rapeseed (e.g. P. parasitica), onion (e.g. P.Peronospora spp. (downy mildew) on tobacco (P. tabacina) and soybean (e.g. P. manshurica); Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybean; Phialophora spp. (e.g. P. tracheiphila and P. tetraspora) and soybean (e.g. P. gregata: stem rot) on grapes; Phoma lingam (Leptosphaeria biglobosa) on rapeseed and cabbage. biglobosa and synonymous with L. maculans: root and stem rot), P. betae on sugar beet (root rot, leaf spot and seedling damping-off) and P. zeae-maydis on maize (synonymous with Phyllostica zeae); Phomopsis on sunflower, grape (e.g. P. viticola: stem and leaf spot) and soybean (e.g. stem rot: P. phaseoli, teleomorph: Diaporthe phaseolorum); Physoderma maydis on maize maydis (brown spot disease); various plants such as peppers and cucurbits (e.g., P. capsici), soybean (e.g., P. megasperma, synonymous with P. sojae), potato and tomato (e.g., P. infestans: leaf rot disease) and deciduous trees (e.g., P. ramorum).ramorum; Phytophthora species (damage, root, leaf, fruit and stem rot) on oak; Plasmodiophora brassicae on cabbage, rapeseed, radish and other plants. brassicae (club root disease); Plasmopara species, e.g. P. viticola (grapevine downy mildew) on grapes and P. halstedii on sunflower; Podosphaera species (powdery mildew) on roses, hops, pome and soft fruits (e.g. P. leucotricha on apples) and cucurbits (P. xanthii); Polymyxa species, e.g. on cereals such as barley and wheat (P. graminis) and sugar beet (P. betae) and the viral diseases transmitted thereby; Pseudocercosporella herpotrichoides on cereals, e.g. wheat or barley. herpotrichoides (synonym: Oculimacula yallundae, O. acuformis: eyespot disease, teleomorph: Tapesia yallundae); Pseudoperonospora (downy mildew) on various plants, e.g. P. cubensis on cucurbits or P. humili on hops; Pseudopezicula tracheifila on grapes; tracheiphila (red fireworks or "rotbrenner", anamorph: Phialophora); Puccinia species (rusts) on various plants, e.g. P. triticina (brown rust or leaf rust), P. striiformis (stripe rust or yellow rust), P. hordei (dwarf rust), P. graminis (P.graminis (stem rust or black rust) or P. recondita (brown rust or leaf rust), P. kuehnii (orange rust) on sugarcane and P. asparagi on asparagus; Pyrenopeziza species, e.g. P. brassicae on rapeseed; Pyrenopeziza species, e.g. P. niger on wheat; Pyrenophora (anamorph: Drechslera) tritici-repentis (tan spot) or P. teres (net blotch) on barley; Pyricularia species, e.g. P. oryzae (teleomorph: Magnaporthe grisea) on rice; grisea (rice blast disease) and P. grisea on turfgrass and cereals; Pythium species (seedling damping off) on turfgrass, rice, corn, wheat, cotton, rapeseed, sunflower, soybean, sugar beet, vegetables and various other plants (e.g. P. ultimum or P. aphanidermatum) and P. oligandrum on mushrooms; Ramularia species, e.g. R. collo-cygni (ramularia leaf spot, physiological leaf spot disease) on barley, R. areola (telemorph: Mycosphaerella areola) on cotton. areola) and R. beticola on sugar beet; Rhizoctonia species on cotton, rice, potato, turfgrass, maize, rapeseed, potato, sugar beet, vegetables and various other plants, such as R. solani on soybean (root and stem rot), R. solani on rice (sheath blight) or R. cerealis on wheat or barley.cerealis (Rhizoctonia spring blight); Rhizopus stolonifer (black mold, soft rot) on strawberry, carrot, cabbage, grapes and tomato; Rhynchosporium secalis and R. commune (fire blight) on barley, rye and triticale; Sarocladium oryzae on rice. oryzae and S. attenuatum (sheath rot); Sclerotinia spp. (stalk rot or white mold) on vegetables (S. minor and S. sclerotiorum) and on agricultural crops such as rapeseed, sunflower (e.g. S. sclerotiorum) and soybean, S. rolfsii on soybean, peanut, vegetables, maize, cereals and ornamentals; (synonym Athelia rolfsii); Septoria spp. on various plants, e.g. S. glycines (brown spot) on soybean, S. tritici (Zymoseptoria spp.) on wheat. tritici, Septoria leaf spot) and S. nodorum (Stagonaspora leaf spot) on cereals; Uncinula (Synonym: Erysiphe) necator (powdery mildew, anamorph: Oidium tuckeri) on grapes; Setosphaeria species (black leaf blight) on maize (e.g. S. turcicum, synonym: Helminthosporium turcicum) and turfgrass; Maize (e.g. S. reiliana): Ustilago reiliana reiliana (smut), Sphacelotheca species (sooty mildew) on sorghum and sugarcane; Sphaerotheca fuliginea on Cucurbitaceae (synonym: Podosphaera xanthii: powdery mildew); Spongospora subterranea on potato (powdery scab) and the viral diseases transmitted by it; Stagonospora species on cereals, e.g. S. nodorum on wheat (Stagonaspora spot, teleomorph: Leptosphaeria [synonym: Phaeosphaeria] nodorum, synonym: Septoria nodorum); Synchytrium endobioticum on potato endobioticum (potato wart); Taphrina species, such as T. deformans (leaf curl) on peaches and T. pruni (plum pocket) on plums; Thielaviopsis species (black root rot) on tobacco, pome fruits, vegetables, soybeans and cotton, such as T. basicola (synonymous with Chalara elegans); Tilletia species (common black ear disease or smut) on cereals, such as T. tritici (synonymous with T. caries, wheat smut) and T. controversa (dwarf smut) on wheat; Trichoderma harzianum on mushrooms. harzianum); Typhula incarnata (gray snow mold) on barley or wheat; Urocystis species, e.g. U. occulta (striped sooty mold) on rye; on vegetables and legumes, such as legumes (e.g. U. appendiculatus, synonym U. phaseoli), sugar beet (e.g. U. betae or U. beticola) (e.g. U. vignae, U. pisci, U.Uromyces spp. (rust) on cereals (e.g. U. nuda and U. avaenae), maize (e.g. U. maydis: maize sooty mold) and sugarcane; Ustilago spp. (smut) on apple (e.g. V. inaequalis) and pear; Venturia species (black scab) on various plants such as fruit and ornamental plants, grapes, soft fruits, vegetables and field crops; and Verticillium species (damaging disease) on various plants such as fruit and ornamental plants, grapes, soft fruits, vegetables and field crops, e.g. V. longisporum on rapeseed, V. dahliae on strawberry, rapeseed, potato and tomato and V. fungicola on mushrooms; Zymoseptoria tritici tritici on cereals.

[0200] The compounds I and compositions thereof are particularly suitable for controlling the causes of the following plant diseases, respectively: rust diseases on soybeans and cereals (e.g. Phakopsora pachyrhizi and P. meibomiae on soybeans; Puccinia tritici and P. striiformis on wheat); fungal diseases on special crops, soybeans, rapeseed and sunflower (e.g. Botrytis cinerea on strawberries and grapes, Sclerotinia sclerotiorum, S. minor and S. rolfsii on rapeseed, sunflower and soybean); Fusarium diseases on cereals (e.g. Fusarium culmorum on wheat). culmorum and F. graminearum); downy mildews on speciality crops (e.g. Plasmopara viticola on grapes, Phytophthora infestans on potatoes); powdery mildews on speciality crops and cereals (e.g. Uncinula necator on grapes, Erysiphe spp. on various speciality crops, Blumeria graminis on cereals); leaf spot diseases on cereals, soybean and maize (e.g. Septoria tritici and S. nodorum on cereals, S. glycines on soybean, Cercospora spp. on maize and soybean).

[0201] The compounds I and their compositions are also suitable for controlling harmful microorganisms in the protection of stored products or harvest and in the protection of materials, respectively.

[0202] The term "stored products or harvested products" is understood to mean natural substances of plant or animal origin and their processed forms for which long-term protection is desired. Stored products of plant origin, such as stems, leaves, tubers, seeds, fruits or grains, can be protected in the freshly harvested state or in processed forms such as pre-drying, wetting, grinding, shredding, pressing, roasting, etc., processes which are also known as post-harvest treatment. Also falling under the definition of stored products is wood in the form of rough wood, such as construction timber, electricity transmission towers and barriers, or in the form of finished products, such as furniture or objects made of wood. Stored products of animal origin are hides, leather, fur, hair, etc. Preferably, "stored products" is understood to mean natural substances of plant origin and their processed forms, more preferably fruits and their processed forms, such as fruits, stone fruits, soft fruits and citrus fruits and their processed forms, where the application of the compound I and its compositions can also prevent adverse effects such as decay, discoloration or mold.

[0203] The term "protection of materials" is understood to mean the protection of technical and non-biological materials, such as adhesives, glues, wood, paper, paperboard, textiles, leather, paint dispersions, plastics, cooling lubricants, fibres or fabrics, from infestation and destruction by harmful microorganisms, such as fungi and bacteria.

[0204] When used in the protection of materials or stored products, the application rates of the active substances depend on the type of application field and on the desired effect. Customary application rates in the protection of materials are from 0.001 g to 2 kg, preferably from 0.005 g to 1 kg, of active substance per cubic meter of treated material.

[0205] Compound I and its compositions, respectively, can be used to improve plant health. The present invention also relates to a method for improving plant health by treating the plant, its propagation material and / or the locus in which the plant is growing or intended to grow with an effective amount of Compound I and its compositions, respectively.

[0206] The term "plant health" is understood to mean the state of a plant and / or its products, determined by several indicators alone or in combination with each other, such as yield (e.g. increased biomass and / or increased content of valuable components), plant vigor (e.g. improved plant growth and / or greening of leaves ("greening effect")), quality (e.g. improved content or composition of certain components) and resistance to abiotic and / or biotic stresses. The above identified indicators of plant health may be interdependent or may result from each other.

[0207] The compounds I are applied as such or in the form of a composition by treating the fungus, the plant, the plant propagation material such as seeds, the soil, the surface, the material or the room to be protected from the attack of the fungus with a fungicidally effective amount of the active substance. Application can be carried out both before and after the infection of the plant, the plant propagation material such as seeds, the soil, the surface, the material or the room with the fungus.

[0208] The agrochemical composition comprises a fungicidally effective amount of compound I. The term "anticidally effective amount" means an amount of the composition or compound I sufficient to control harmful fungi on cultivated plants or to protect stored products or harvested materials or materials and not to cause substantial damage to the treated plants, treated stored products or harvested materials or materials. Such amounts can vary within a wide range and depend on various factors, such as the fungal species to be controlled, the cultivated plants, stored products, harvested materials or materials to be treated, the climatic conditions and the specific compound I used.

[0209] The plant propagation material can be treated prophylactically with Compound I on its own or with a composition comprising at least one compound I either at the time of planting or transplanting or before.

[0210] When used for plant protection, the amount of active substance applied is, depending on the type of effect desired, between 0.001 and 2 kg / ha, preferably between 0.005 and 2 kg / ha, more preferably between 0.05 and 0.9 kg / ha, in particular between 0.1 and 0.75 kg / ha.

[0211] In the treatment of plant propagation material, such as seeds, for example by dusting, coating or drenching, generally an amount of active substance of 0.1 to 1000 g, preferably 1 to 1000 g, more preferably 1 to 100 g, most preferably 5 to 100 g per 100 kg of plant propagation material (preferably seeds) is required.

[0212] The user usually applies the agrochemical composition from a pre-dosed device, a backpack sprayer, a spray tank, a spray plane or an irrigation system. Usually, the agrochemical composition is made up to the desired application concentration with water, buffers and / or further auxiliaries, thus obtaining the ready-to-use spray solution or agrochemical composition according to the invention. Usually, 20 to 2000 liters, preferably 50 to 400 liters, of ready-to-use spray solution are applied per hectare of agriculturally useful area.

[0213] The compounds I, their N-oxides and salts can be converted into conventional types of pesticide compositions, such as solutions, emulsifiable concentrates, suspensions, dusts, powders, pastes, granules, presses, capsules, and mixtures thereof. Examples of composition types (see "Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 6 th(see also Ed. May 2008, CropLife International) are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsifiable concentrates (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, pastilles, wettable powders or dusts (e.g. WP, SP, WS, DP, DS), presses (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN), as well as gel formulations (e.g. GF) for the treatment of plant propagation materials such as seeds. The compositions are prepared in a known manner, for example as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or by Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005. The present invention also relates to an agrochemical composition comprising an adjuvant and at least one compound I.

[0214] Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesives, thickeners, moisturizers, repellents, attractants, feeding stimulants, compatibilizers, bactericides, antifreeze agents, antifoaming agents, colorants, tackifiers and binders.

[0215] Suitable solvents and liquid carriers are water and organic solvents, such as medium to high boiling mineral oil fractions, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e.g. toluene, paraffins, tetrahydronaphthalene and alkylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzyl alcohol, cyclohexanol, glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g. lactate esters, carbonate esters, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamide; and mixtures thereof.

[0216] Suitable solid carriers or fillers are mineral earths, such as silicates, silica gel, talc, kaolin, limestone, lime, chalk, clay, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, such as cellulose, starch; fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea; products of vegetable origin, such as grain meals, bark meals, wood meals, nut shell meals and mixtures thereof.

[0217] Suitable surfactants are surface active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof.Such surfactants can be used as emulsifiers, dispersants, solubilizers, wetting agents, penetration enhancers, protective colloids or adjuvants.Examples of surfactants are listed in McCutcheon's, Vol.1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).

[0218] Suitable anionic surfactants are the alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates and their mixtures.Examples of sulfonates are alkylarylsulfonates, diphenylsulfonates, alpha-olefinsulfonates, ligninsulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates.Examples of sulfates are sulfates of fatty acids, oils, ethoxylated alkylphenols, alcohols, ethoxylated alcohols or fatty acid esters.Examples of phosphates are phosphate esters.Examples of carboxylates are alkyl carboxylates and carboxylated alcohol or alkylphenol ethoxylates.

[0219] Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters, alkoxylated with 1 to 50 equivalents. For alkoxylation, ethylene oxide and / or propylene oxide, preferably ethylene oxide, can be used. Examples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters, or monoglycerides. Examples of sugar surfactants are sorbitan, ethoxylated sorbitan, sucrose and glucose esters, or alkyl polyglucosides. Examples of polymeric surfactants are homopolymers or copolymers of vinylpyrrolidone, vinyl alcohol, or vinyl acetate.

[0220] Suitable cationic surfactants are quaternary surfactants, such as quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetaines and imidazolines. Suitable block polymers are block polymers of the AB or ABA type, containing blocks of polyethylene oxide and polypropylene oxide, or of the ABC type, containing alkanol, polyethylene oxide, and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or polyethyleneamines.

[0221] Suitable adjuvants are compounds that have negligible or no insecticidal activity by themselves and improve the biological performance of compound I against the target. Examples are surfactants, mineral or vegetable oils, and other auxiliaries. Further examples are listed in Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.

[0222] Suitable thickening agents are polysaccharides (eg, xanthan gum, carboxymethylcellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates.

[0223] Suitable fungicides are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones.

[0224] Suitable antifreeze agents are ethylene glycol, propylene glycol, urea and glycerin.

[0225] Suitable antifoaming agents are silicones, long chain alcohols, and salts of fatty acids.

[0226] Suitable colorants (e.g. red, blue or green) are pigments with low water solubility and water soluble dyes. Examples are inorganic colorants (e.g. iron oxide, titanium oxide, iron hexacyanoferrate) and organic colorants (e.g. alizarin colorants, azo colorants and phthalocyanine colorants).

[0227] Suitable tackifiers or binders are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, polyacrylates, biological or synthetic waxes, and cellulose ethers.

[0228] The agrochemical composition generally comprises 0.01 to 95% by weight, preferably 0.1 to 90% by weight, more preferably 1 to 70% by weight, in particular 10 to 60% by weight of active substance (e.g. at least one compound I). The agrochemical composition generally comprises 5 to 99.9% by weight, preferably 10 to 99.9% by weight, more preferably 30 to 99% by weight, in particular 40 to 90% by weight of at least one adjuvant. The active substance (e.g. compound I) is used with a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum).

[0229] For the treatment of plant propagation material, especially seeds, seed treatment solutions (LS), suspoemulsions (SE), flowable concentrates (FS), dry treatment powders (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsifiable concentrates (ES), emulsifiable concentrates (EC) and gels (GF) are commonly used.

[0230] The subject compositions, after 2-10-fold dilution, give active substance concentrations of 0.01-60% by weight, preferably 0.1-40%, in ready-to-use formulations. Application can be carried out before or during sowing. Methods for applying the compounds I and their compositions, respectively, to plant propagation material, in particular to seeds, include dressing, coating, pelleting, dusting, immersion, and in-sowing application methods. Preferably, the compounds I or their compositions, respectively, are applied to the plant propagation material by methods that do not induce germination, for example by seed dressing, pelleting, coating, and dusting.

[0231] Various types of oils, wetting agents, adjuvants, fertilizers or micronutrients, and additional pesticides (e.g., fungicides, growth regulators, herbicides, insecticides, safeners) may be added to the compound I or compositions thereof as a premix or may not be added until just before use (tank mix). These agents may be mixed with the compositions according to the invention in a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.

[0232] Pesticides are generally chemical or biological agents (such as pesticidal active ingredients, compounds, compositions, viruses, bacteria, antimicrobial agents, or fungicides) whose effects deter, incapacitate, kill, or otherwise destroy pests. Target pests include insects, plant pathogens, weeds, mollusks, birds, mammals, fish, nematodes (roundworms), and microorganisms that destroy property, are a nuisance, spread disease, or transmit disease. The term "pesticide" also includes plant growth regulators that change the expected growth, flowering, or reproduction rate of plants; defoliants that cause leaves or other foliage to fall from plants, usually to facilitate harvesting; desiccants that promote drying of living tissues, such as unwanted plant tops; plant activators that activate plant physiology for protection against certain pests; antidotes that reduce the undesirable herbicidal effects of pesticides on crop plants; and plant growth promoters that affect plant physiology, for example, to increase plant growth, biomass, yield, or any other quality parameter of the harvestable product of crop plants.

[0233] Biopesticides are defined as forms of pesticides based on microorganisms (bacteria, fungi, viruses, nematodes, etc.) or natural products (chemical compounds such as metabolites, proteins, or extracts from organisms or other natural sources) (US Environmental Protection Agency: http: / / www.epa.gov / pesticides / biopesticides / ). Biopesticides are divided into two main classes, microbial pesticides and biochemical pesticides: (1) Microbial pesticides consist of bacteria, fungi, or viruses (and often contain metabolic products produced by bacteria and fungi). Entomopathogenic nematodes are also multicellular but are classified as microbial pesticides. (2) Biochemical pesticides are naturally occurring substances that control pests or provide other crop protection uses as defined below, but which are relatively nontoxic to mammals.

[0234] The mixture of the compounds I in their fungicidal use form or compositions containing them with other fungicides often results in an expansion of the fungicidal spectrum of activity or in the prevention of the development of fungicide resistance. Furthermore, synergistic effects are often obtained (synergistic mixtures).

[0235] The following list of pesticides II that can be used in combination with compounds I is intended to illustrate, but not limit, the possible combinations: A) Respiratory inhibitors - Q oInhibitors of complex III at the site: azoxystrobin (A.1.1), coumetoxystrobin (A.1.2), coumoxystrobin (A.1.3), dimoxystrobin (A.1.4), enestrobulin (A.1.5), phenaminestrobin (A.1.6), phenoxystrobin / flufenoxystrobin (A.1.7), fluoxastrobin (A.1.8), kresoxime-methyl (A.1.9), mandestrobin (A.1.10), metomino. Strobin (A.1.11), Orysastrobin (A.1.12), Picoxystrobin (A.1.13), Pyraclostrobin (A.1.14), Pyrametstrobin (A.1.15), Pyraoxystrobin (A.1.16), Trifloxystrobin (A.1.17), 2-(2-(3-(2,6-dichlorophenyl)-1-methyl-allylideneaminooxymethyl)-phenyl)-2-methoxyimino-N-methyl-acetamide (A.1.18), Piribe carb (A.1.19), triclopyricarb / chlorozinecarb (A.1.20), famoxadone (A.1.21), fenamidone (A.1.21), methyl-N-[2-[(1,4-dimethyl-5-phenyl-pyrazol-3-yl)oxylmethyl]phenyl]-N-methoxy-carbamate (A.1.22), methyltetraprole (A.1.25), (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]-oxy-2-methyl methoxyimino-N,3-dimethyl-pent-3-enamide (A.1.34), (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (A.1.35), pyriminostrobin (A.1.36), bifujunchi (A.1.37), 2-(ortho-((2,5-dimethylphenyl-oxymethylene)phenyl)-3-methoxy-acrylic acid methyl ester (A.1.38); - Q iInhibitors of complex III at the site: cyazofamid (A.2.1), amisulbrom (A.2.2), [(6S,7R,8R)-8-benzyl-3-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]2-methylpropanoate (A.2.3), fenpicoxamide (A.2.4), florylpicoxamide (A.2.5), methallylpicoxamide (A.2.6); - inhibitors of complex II: benodanil (A.3.1), benzovindiflupyr (A.3.2), bixafen (A.3.3), boscalid (A.3.4), carboxin (A.3.5), fenfuram (A.3.6), fluopyram (A.3.7), flutolanil (A.3.8), fluxapyroxad (A.3.9), furametpyr (A.3.10), isofetamide (A.3.11), isopyrazam (A.3.12), mepronil (A.3.13), oxycarboxin (A.3.14), penflufen (A.3.15); Penthiopyrad (A.3.16), pydiflumetofen (A.3.17), pyraziflumide (A.3.18), sedaxane (A.3.19), tecloftalam (A.3.20), thifluzamide (A.3.21), impirfluxam (A.3.22), pyrapropoin (A.3.23), fluindapyr (A.3.28), N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-5-fluoro-1-methyl-pyrazole-4-carboxamide (A.3.29), methyl( E)-2-[2-[(5-cyano-2-methyl-phenoxy)methyl]phenyl]-3-methoxy-prop-2-enoate (A.3.30), isoflucipram (A.3.31), 2-(difluoromethyl)-N-(1,1,3-trimethyl-indan-4-yl)pyridine-3-carboxamide (A.3.32), 2-(difluoromethyl)-N-[(3R)-1,1,3-trimethylindan-4-yl]pyridine-3-carboxamide (A.3.33), 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (A.3.34), 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (A.3.35), 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)pyridine-3-carboxamide (A.3.36), 2-(difluoromethyl)-N-[(3R)-1,1-dimethyl-3-propyl-indan-4-yl]pyridine-3-carboxamide (A.3.37), 2-(difluoromethyl)-N-(3-isobutyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide (A.3.38), 2-(difluoromethyl)-N-[(3R)-3-isobutyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (A.3.39), cyclobutrifluram (A.3.24);. - other respiratory inhibitors: diflumetrim (A.4.1); nitrophenyl derivatives: binapacryl (A.4.2), dinobuton (A.4.3), dinocap (A.4.4), fluazinam (A.4.5), meptyldinocap (A.4.6), ferimzone (A.4.7); organometallic compounds: fentin salts, e.g. fentin acetate (A.4.8), fentin chloride (A.4.9) or fentin hydroxide (A.4.10); amethoctrazine (A.4.11); silthiofam (A.4.12); B) Sterol biosynthesis inhibitors (SBI fungicides) - C14 demethylase inhibitors: Triazoles: Azaconazole (B.1.1), Bitertanol (B.1.2), Bromuconazole (B.1.3), Cyproconazole (B.1.4), Difenoconazole (B.1.5), Diniconazole (B.1.6), Diniconazole-M (B.1.7), Epoxiconazole (B.1.8), Fenbuconazole (B.1.9), Fluquinconazole (B.1.10), Flusilazole (B.1.11), Flutriafol (B.1.12), .12), hexaconazole (B.1.13), imibenconazole (B.1.14), ipconazole (B.1.15), metconazole (B.1.17), myclobutanil (B.1.18), oxpoconazole (B.1.19), paclobutrazol (B.1.20), penconazole (B.1.21), propiconazole (B.1.22), prothioconazole (B.1.23), simeconazole (B.1.24), tebuconazole (B.1.25), tetraconazole (B.1.26), 2-(2,4-Difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(2,2,2-trifluoroethoxy)phenyl]-2-pyridyl]propan-2-ol (B.1.31), 2-(2,4-Difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(2,2,2-trifluoroethoxy)phenyl]-2-pyridyl]propan-2-ol (B.1.32), 2-(2,4-Difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(2,2,2-trifluoroethoxy)phenyl]-2-pyridyl]propan-2-ol (B.1.33), 2-(2,4-Difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(2,2,2-trifluoroethoxy)phenyl]-2-pyridyl]propan-2-ol (B.1.34), 2-(2,4-Difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(2,2,2-trifluoroethoxy)phenyl]-2-pyridyl]propan-2-ol (B.1.35), 2-(2,4-Difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(2,2,2-trifluoroethoxy)phenyl]-2-pyridyl]propan-2-ol (B.1.36), 2-(2,4-Difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(2,2,2-trifluoroethoxy)phenyl]-2-pyridyl] Tetrazol-1-yl)-1-[5-[4-(trifluoromethoxy)phenyl]-2-pyridyl]propan-2-ol (B.1.32), 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-sulfanyl-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile (B.1.33), ipfentrifluconazole (B.1.37), mefentrifluconazole (B.1.38), and benzonitrile (B.1.39).38), (2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, (2S)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 2-(chloromethyl)-2-methyl-5-( p-Tolyl-methyl)-1-(1,2,4-triazol-1-ylmethyl)cyclopentanol (B.1.43); Imidazoles: Imazalil (B.1.44), Pefurazoate (B.1.45), Prochloraz (B.1.46), Triflumizole (B.1.47); Pyrimidines, pyridines, piperazines: Fenarimol (B.1.49), Pyriphenox (B.1.50), Trifoxicam (B.1.51), Trifoxicam (B.1.52), Trifoxicam (B.1.53), Trifoxicam (B.1.54), Trifoxicam (B.1.55), Trifoxicam (B.1.56), Trifoxicam (B.1.57), Trifoxicam (B.1.58), Trifoxicam (B.1.59), Trifoxicam (B.1.60), Trifoxicam (B.1.61), Trifoxicam (B.1.62), Trifoxicam (B.1.63), Trifoxicam (B.1.64), Trifoxicam (B.1.65), Trifoxicam (B.1.66), Trifoxicam (B.1.67), Trifoxicam (B.1.68), Trifoxicam (B.1.69), Trifoxicam (B.1.70), Trifoxicam (B.1.71), Trifoxicam (B.1.72), Trifoxicam (B.1.73), Trifoxicam (B.1.74), Trifoxicam (B.1.75), Trifoxicam (B.1.76), Trifoxicam (B.1.77), Trifoxicam (B.1.78), Trifoxicam (B.1.79), Trifoxicam (B.1.80), Trifoxicam (B.1.81), Trifoxicam (B Phosphorus (B.1.51), [3-(4-chloro-2-fluoro-phenyl)-5-(2,4-difluorophenyl)isoxazol-4-yl]-(3-pyridyl)methanol (B.1.52), 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzoni tolyl (B.1.53), 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol (B.1.54), 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol (B.1.55);. - Delta 14-reductase inhibitors: aldimorph (B.2.1), dodemorph (B.2.2), dodemorph-acetate (B.2.3), fenpropimorph (B.2.4), tridemorph (B.2.5), fenpropidin (B.2.6), piperalin (B.2.7), spiroxamine (B.2.8); - 3-ketoreductase inhibitors: fenhexamid (B.3.1); - Other sterol biosynthesis inhibitors: chlorfenomizole (B.4.1); C) Nucleic acid synthesis inhibitors - phenylamide or acylamino acid fungicides: benalaxyl (C.1.1), benalaxyl-M (C.1.2), chiralaxyl (C.1.3), metalaxyl (C.1.4), metalaxyl-M (C.1.5), ofrace (C.1.6), oxadixyl (C.1.7); - other nucleic acid synthesis inhibitors: hymexazol (C.2.1), octhilinone (C.2.2), oxolinic acid (C.2.3), bupirimate (C.2.4), 5-fluorocytosine (C.2.5), 5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine (C.2.6), 5-fluoro-2-(4-fluorophenylmethoxy)pyrimidin-4-amine (C.2.7), 5-fluoro-2(4-chlorophenylmethoxy)pyrimidin-4-amine (C.2.8); D) Inhibitors of cell division and the cytoskeleton - Tubulin inhibitors: benomyl (D.1.1), carbendazim (D.1.2), fuberidazole (D.1.3), thiabendazole (D.1.4), thiophanate-methyl (D.1.5), pyridaclomethyl (D.1.6), N-ethyl-2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]butanamide (D.1.8), N-ethyl-2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methylsulfanyl-acetamide (D.1.9), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)butanamide (D.1.10), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)-2-methoxy-acetamide (D.1.11), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-propyl-butanamide (D.1.12), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methoxy-N-propyl-acetamide (D.1.13), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methylsulfanyl-N-propyl-acetamide (D.1.14), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)-2-methylsulfanyl-acetamide (D.1.15), 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine (D.1.16); - Other cytostatics: diethofencarb (D.2.1), ethaboxam (D.2.2), pencycuron (D.2.3), fluopicolide (D.2.4), zoxamide (D.2.5), metrafenone (D.2.6), pyriophenone (D.2.7), fenamacril (D.2.8); E) Amino acid and protein synthesis inhibitors - Methionine synthesis inhibitors: cyprodinil (E.1.1), mepanipyrim (E.1.2), pyrimethanil (E.1.3); - Protein synthesis inhibitors: blasticidin-S (E.2.1), kasugamycin (E.2.2), kasugamycin hydrochloride-hydrate (E.2.3), mildiomycin (E.2.4), streptomycin (E.2.5), oxytetracycline (E.2.6); F) Signal transduction inhibitors - MAP / histidine kinase inhibitors: fluoroimide (F.1.1), iprodione (F.1.2), procymidone (F.1.3), vinclozolin (F.1.4), fludioxonil (F.1.5); - G protein inhibitors: quinoxyfen (F.2.1); G) Lipid and membrane synthesis inhibitors - phospholipid biosynthesis inhibitors: edifenphos (G.1.1), iprobenfos (G.1.2), pyrazophos (G.1.3), isoprothiolane (G.1.4); - Lipid peroxidation: dicloran (G.2.1), quintozene (G.2.2), tecnazene (G.2.3), tolclofos-methyl (G.2.4), biphenyl (G.2.5), chloroneb (G.2.6), etridiazole (G.2.7), zinc thiazole (G.2.8); - Phospholipid biosynthesis and cell wall deposition: dimethomorph (G.3.1), flumorph (G.3.2), mandipropamid (G.3.3), pyrimorph (G.3.4), benthiavalicarb (G.3.5), iprovalicarb (G.3.6), valifenalate (G.3.7); - Compounds affecting cell membrane permeability and fatty acids: propamocarb (G.4.1); - Inhibitors of oxysterol binding proteins: oxathiapiproline (G.5.1), fluoxapiproline (G.5.3), 4-[1-[2-[3-(difluoromethyl)-5-methyl-pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.4), 4-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]- N-tetralin-1-yl-pyridine-2-carboxamide (G.5.5), 4-[1-[2-[3-(difluoromethyl)-5-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.6), 4-[1-[2-[5-cyclopropyl-3-(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1 -yl-pyridine-2-carboxamide (G.5.7), 4-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.8), 4-[1-[2-[5-(difluoromethyl)-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.9), ruboxamide (G.5.9), 4-[1-[2-[3,5-bis(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.10), (4-[1-[2-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.11); H) Multi-site inhibitors - inorganic active substances: Bordeaux mixture (H.1.1), copper (H.1.2), copper acetate (H.1.3), copper hydroxide (H.1.4), copper oxychloride (H.1.5), basic copper sulfate (H.1.6), sulfur (H.1.7); - Thio- and dithiocarbamates: ferbam (H.2.1), mancozeb (H.2.2), maneb (H.2.3), metam (H.2.4), metiram (H.2.5), propineb (H.2.6), thiram (H.2.7), zineb (H.2.8), ziram (H.2.9); - Organic chlorine compounds: anilazine (H.3.1), chlorothalonil (H.3.2), captafol (H.3.3), captan (H.3.4), folpet (H.3.5), dichlofluanid (H.3.6), dichlorophen (H.3.7), hexachlorobenzene (H.3.8), pentachlorophenol (H.3.9) and its salts, phthalide (H.3.10), tolylfluanid (H.3.11); - Guanidines and others: Guanidine (H.4.1), Dodine (H.4.2), Dodine free base (H.4.3), Guazatine (H.4.4), Guazatine-acetate (H.4.5), Iminooctadine (H.4.6), Iminooctadine-triacetate (H.4.7), Iminooctadine-tris(arbesilate) (H.4.8), Dithianone (H.4.9), 2,6-Dimethyl-1H,5H-[1,4]dithino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetraone (H.4.10); I) Cell wall synthesis inhibitors - Glucan synthesis inhibitors: validamycin (I.1.1), polyoxin B (I.1.2); - Melanin synthesis inhibitors: pyroquilon (I.2.1), tricyclazole (I.2.2), carpropamid (I.2.3), dicyclomet (I.2.4), fenoxanil (I.2.5); J) Plant defense inducers - Acibenzolar-S-methyl (J.1.1), Probenazole (J.1.2), Isotianil (J.1.3), Thiadinil (J.1.4), Prohexadione-calcium (J.1.5);Phosphonates: Fosetyl (J.1.6), Fosetyl-aluminium (J.1.7), Phosphorous acid and its salts (J.1.8), Calcium phosphonate (J.1.11), Potassium phosphonate (J.1.12), Potassium or sodium bicarbonate (J.1.9), 4-Cyclopropyl-N-(2,4-dimethoxyphenyl)thiadiazole-5-carboxamide (J.1.10); K) Mechanism of action unknown - Bronopol (K.1.1), Quinomethionate (K.1.2), Cyflufenamid (K.1.3), Cymoxanil (K.1.4), Dazomet (K.1.5), Debacarb (K.1.6), Diclocymet (K.1.7), Diclomedine (K.1.8), Difenzoquat (K.1.9), Difenzoquat-methylsulfate (K.1.10), Diphenylamine (K.1.11), Fenitropan (K.1.12), Fenpyrazamine (K.1.13), Flumetober (K.1.14), Flusulfamide (K.1.15), .1.15), flutianil (K.1.16), harpin (K.1.17), methasulfocarb (K.1.18), nitrapyrin (K.1.19), nitrothal-isopropyl (K.1.20), tolprocarb (K.1.21), oxine-copper (K.1.22), proquinazid (K.1.23), tebufloquine (K.1.24), tecloftalam (K.1.25), triazoxide (K.1.26), N'-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N'-phenyl- -Methylformamidine (K.1.27), N'-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methylformamidine (K.1.28), N'-[4-[[3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl]oxy]-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine (K.1.29), N'-(5-bromo-6-indan-2-yloxy-2-methyl-3-pyridyl)-N-ethyl-N -methyl-formamidine (K.1.30), N'-[5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.31), N'-[5-bromo-6-(4-isopropylcyclohexoxy)-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.32), N'-[5-bromo-2-methyl-6-(1-phenylethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.33), N'-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methylformamidine (K.1.34), N'-(5-difluoromethyl-2-methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methylformamidine (K.1.35), 2-(4-chloro-phenyl)-N-[4-(3,4-dimethoxy-phenyl)-isoxazol-5-yl]-2-prop-2-ynyloxy-acetamide (K.1.36), 3-[5 -(4-Chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine (pyrisoxazole) (K.1.37), 3-[5-(4-methylphenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine (K.1.38), 5-chloro-1-(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1H-benzimidazole (K.1.39), ethyl (Z)-3-amino-2-cyano-3-phenyl-prop-2-enoate (K.1.40), Picarburazox (K.1.41), Pentyl N -[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate (K.1.42), but-3-ynyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate (K.1.43), ipflufenoquine (K.1.44), quinofumelin (K.1.47), bendiothiazolinone (K.1.48), bromothalonil (K.1.49), 2-(6-benzyl-2-pyridyl)quina quinazoline (K.1.50), 2-[6-(3-fluoro-4-methoxy-phenyl)-5-methyl-2-pyridyl]quinazoline (K.1.51), diclobenchiazox (K.1.52), N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine (K.1.53), aminopyrifen (K.1.54), fluopimomide (K.1.55), N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.56), N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine (K.1.57), N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide (K.1.58), N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide (K.1.59), N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide (WO 2018 / 177894, WO 2020 / 212513);. L) Biopesticides L1) Microbial pesticides with fungicidal, bactericidal, virucidal and / or plant defense activator activity: Ampelomyces quisqualis, Aspergillus flavus, Aureobasidium pullulans, Bacillus altitudinis, B. amyloliquefaciens, B. amyloliquefaciens subsp. plantarum. ssp.plantarum (also called B.velezensis), B.megaterium, B.mojavensis, B.mycoides, B.pumilus, B.simplex, B.solisalsi, B.subtilis, B.subtilis var.amyloliquefaciens, B.velezensis, Candida oleophila, C.saitoana, Clavibacter michiganensis, michiganensis (bacteriophage), Coniothyrium minitans, Cryphonectria parasitica, Cryptococcus albidus, Dilophosphora alopecuri, Fusarium oxysporum, Clonostachys rosea f.catenulate (also named Gliocladium catenulate), Gliocladium roseum, Lysobacter antibioticus, L. enzymogenes, Metschnikowia fructicola, Microdochium dimerum, Microsphaeropsis ochracea, Muscodor albus, Paenibacillus alvei, Paenibacillus epiphyticus, P. polymyxa, Pantoea bagans, vagans, Penicillium bilaiae, Phlebiopsis gigantea, Pseudomonas sp., Pseudomonas chloraphis, Pseudozyma flocculosa, Pichia anomala, Pythium oligandrum, Sphaerodes mycoparasitica, Streptomyces griseoviridis, S. lydicus, S. violaceusniger, Talaromyces flavus flavus, Trichoderma asperelloides, T. asperellum, T. atroviride, T. fertile, T. gamsii, T. harmatum, T.T. harzianum, T. polysporum, T. stromaticum, T. virens, T. viride, Typhula phacorrhiza, Ulocladium oudemansii, Verticillium dahlia, Zucchini yellow mosaic virus (non-virulent strain);. L2) Biochemical pesticides with fungicidal, bactericidal, virucidal and / or plant defense activator activity: harpin protein, Reynoutria sachalinensis extract; L3) Microbial pesticides with insecticidal, acaricidal, molluscicidal and / or nematocidal activity: Agrobacterium radiobacter, Bacillus cereus, B. firmus, B. thuringiensis, B. thuringiensis ssp. aizawai, Bt ssp. israelensis, Bt ssp. galleriae, Bt ssp. kurstaki, Bt ssp. tenebrionis, Beauveria bassiana bassiana, B. bronniartii, Burkholderia spp., Chromobacterium subtsugae, Cydia pomonella granulovirus (CpGV), Cryptophlebia leucotreta granulovirus (CrleGV), Flavobacterium spp., Helicoverpa armigera nucleopolyhedrovirus (HearNPV), Helicoverpa zea nucleopolyhedrovirus (HearNPV), Helicoverpa zea nucleopolyhedrovirus (HearNPV), Helicoverpa zea granulo ... nucleopolyhedrovirus (HzNPV), Helicoverpa zea single capsid nucleopolyhedrovirus (HzSNPV), Heterorhabditis bacteriophora, Isaria fumosorosea, Lecanicillium longisporum, L. muscarium, L.muscarium, Metarhizium anisopliae, M. anisopliae var. anisopliae, M. anisopliae var. acridum, Nomuraea rileyi, Paecilomyces fumosoroseus, P. lilacinus, Paenibacillus popilliae, Pasteuria sp. spp., P. nishizawae, P. penetrans, P. ramosa, P. thornea, P. usgae, Pseudomonas fluorescens, Spodoptera littoralis nucleopolyhedrovirus (SpliNPV), Steinernema carpocapsae, S. feltiae, S. kraussei, Streptomyces galbus, S. microflavus;. L4) Biochemical pesticides with insecticidal, acaricidal, molluscicidal, pheromone and / or nematocidal activity; L-carvone, citral, (E,Z)-7,9-dodecadien-1-yl acetate, ethyl formate, (E,Z)-2,4-ethyldecadienoate (pea ester), (Z,Z,E)-7,11,13-hexadecatrienal, heptyl butyrate, isopropyl myristate, rabanuryl senecioate, cis-jasmone, 2-methyl 1-Butanol, Methyl Eugenol, Methyl Jasmonate, (E,Z)-2,13-Octadecadien-1-ol, (E,Z)-2,13-Octadecadien-1-ol Acetate, (E,Z)-3,13-Octadecadien-1-ol, (R)-1-Octen-3-ol, Pentatermanone, (E,Z,Z)-3,8,11-Tetradecatrienyl Acetate, (Z,E)-9,12-Tetradecadien-1-yl Acetate, (Z)-7-Tetradecen-2-one, (Z)-9-Tetradecen-1-yl Acetate, (Z)-11-Tetradecenal, (Z)-11-Tetradecen-1-ol, Extract of Chenopodium ambrosiodes; Neem Oil, Extract of Chenopodium ambrosiodes; L5) Microbial pesticides with plant stress reducing activity, plant growth regulator activity, plant growth promoting activity and / or yield enhancing activity: Azospirillum amazonense, A. brasilense, A. lipoferum, A. irakense, A. halopraeferens, Bradyrhizobium spp., B. elkanii, B. japonicum, B. liaoningense, B. lupini, Delftia acidovorans, Glomus intraradices, intraradices, Mesorhizobium spp., Rhizobium leguminosarum bv. phaseoli, Rlbv. trifolii, Rlbv. viciae, R. tropici, Sinorhizobium meliloti; O) Insecticides of classes O.1 to O.29 O.1 Acetylcholinesterase (AChE) inhibitors: aldicarb, alanycarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb, triazamate; acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyphos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos / DDVP, dicrotophos, dimethoate, dimethy Rubinphos, Disulfoton, EPN, Ethion, Ethoprophos, Famflu, Fenamiphos, Fenitrothion, Fenthion, Fosthiazate, Heptenophos, Imicyaphos, Isofenphos, Isopropyl O-(methoxyaminothio-phosphoryl) salicylate, Isoxathion, Malathion, Mecarbam, Methamidophos, Methidathion, Mevinphos, Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion, Parathion-methyl, Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimiphos-methyl, Profenofos, Propetamphos, Prothiofos, Pyraclofos, Pyridaphenthion, Quinalphos, Sulfotep, Tebupirimphos, Temephos, Terbufos, Tetrachlorvinphos, Thiometon, Triazophos, Trichlorfon, Vamidothion; O.2 GABA-gated chloride channel antagonists: endosulfan, chlordane; ethiprole, fipronil, flufiprole, pyrafluprole, pyriprole; O.3 Sodium channel modulators: Acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, kappa-bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, dita-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate , etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, heptafluthrin, imiprothrin, meperfluthrin, metofluthrin, momflufluorothrin, epsilon-momfluorothrin, permethrin, fenothrin, prallethrin, profluthrin, pyrethrins (pyrethrum), resmethrin, silafluofen, tefluthrin, kappa-tefluthrin, tetramethylfluthrin, tetramethrin, tralomethrin, transfluthrin; DDT, methoxychlor; O.4 Nicotinic acetylcholine receptor (nAChR) agonists: acetamiprid, clothianidin, cycloxapride, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam; 4,5-dihydro-N-nitro-1-(2-oxiranylmethyl)-1H-imidazol-2-amine, (2E)-1-[(6-chloropyridin-3-yl)methyl]-N'-nitro-2-pentylidenehydrazinecarboximidamide; 1-[(6-chloro pyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridine;nicotine;sulfoxaflor, flupyradifurone, triflumezopyrim, (3R)-3-(2-chlorothiazol-5-yl)-8-methyl-5-oxo-6-phenyl-2,3-dihydrothiazolo[3,2-a]pyrimidin-8-ium-7-olate, (3S)-3-(6-chloro-3-pyridinyl)methyl (3S)-8-methyl-5-oxo-6-phenyl-3-pyrimidin-5-yl-2,3-dihydrothiazolo[3,2-a]pyrimidin-8-ium-7-olate, (3R)-3-(2-chlorothiazol-5-yl)-8-methyl-5-oxo-6-[3-(trifluoromethyl)phenyl]-2,3-dihydrothiazolo[3,2-a]pyrimidin-8-ium-7-olate, (3S)-8-methyl-5-oxo-6-phenyl-3-pyrimidin-5-yl-2,3-dihydrothiazolo[3,2-a]pyrimidin-8-ium-7-olate, (3R)-3-(2-chlorothiazol-5-yl)-8-methyl-5-oxo-6-[3-(trifluoromethyl)phenyl]-2,3-dihydrothiazolo[3,2-a]pyrimidin- Azolo[3,2-a]pyrimidin-8-ium-7-olate;(3R)-3-(2-chlorothiazol-5-yl)-6-(3,5-dichlorophenyl)-8-methyl-5-oxo-2,3-dihydrothiazolo[3,2-a]pyrimidin-8-ium-7-olate,(3R)-3-(2-chlorothiazol-5-yl)-8-ethyl-5-oxo-6-phenyl-2,3-dihydrothiazolo[3,2-a]pyrimidin-8-ium-7-olate; O.5 Nicotinic acetylcholine receptor allosteric activators: spinosad, spinetoram; O.6 Chloride channel activators: abamectin, emamectin benzoate, ivermectin, lepimectin, milbemectin; O.7 Juvenile hormone mimetics: hydroprene, kinoprene, methoprene; fenoxycarb, pyriproxyfen; O.8 Other non-specific (multi-site) inhibitors: methyl bromide and other alkyl halides; chloropicrin, sulfuryl fluoride, borax, tartar emetic; O.9 Chordotonal organ TRPV channel modulators: pymetrozine, pyrifluquinazone; O.10 Mite growth inhibitors: Clofentezine, hexythiazox, diflovidazine; etoxazole; O.11 Microbial disruptors of insect midgut membrane: Bacillus thuringiensis, Bacillus sphaericus and the insecticidal proteins they produce: Bacillus thuringiensis subsp. Israelensis, Bacillus sphaericus, Bacillus thuringiensis subsp. aizawai, Bacillus thuringiensis subsp. kurstaki, Bacillus thuringiensis subsp. tenebrionis subsp. Tenebrionis), Bt crop proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34 / 35Ab1; O.12 Inhibitors of mitochondrial ATP synthase: diafenthiuron; azocyclotin, cyhexatin, fenbutatin oxide, propargite, tetradifon; O.13 Amplification of oxidative phosphorylation via disruption of the proton gradient: chlorfenapyr, DNOC, sulfuramide; O.14 Nicotinic acetylcholine receptor (nAChR) channel blockers: bensultap, cartap hydrochloride, thiocyclam, thiosultap sodium; O.15 Chitin biosynthesis inhibitors type 0: bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron; O.16 Chitin biosynthesis inhibitors type 1: buprofezin; O.17 Molting disruptors: Cyromazine; O.18 Ecdysone receptor agonists: methoxyfenozide, tebufenozide, halofenozide, fufenozide, chromafenozide; O.19 Octopamine receptor agonists: Amitraz; O.20 Mitochondrial complex III electron transport inhibitors: hydramethylnon, acequinocyl, fluacrylpyrim, bifenazate; O.21 Mitochondrial complex I electron transport inhibitors: fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad, rotenone; O.22 Voltage-dependent sodium channel blockers: indoxacarb, metaflumizone, 2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]-hydrazinecarboxamide, N-(3-chloro-2-methylphenyl)-2-[(4-chlorophenyl)-[4[methyl(methylsulfonyl)amino]phenyl]methylene]-hydrazinecarboxamide; O.23 Inhibitors of acetyl-CoA carboxylase: spirodiclofen, spiromesifen, spirotetramat, spiropydione; O.24 Mitochondrial complex IV electron transport inhibitors: aluminum phosphide, calcium phosphide, phosphine, zinc phosphide, cyanide; O.25 Mitochondrial complex II electron transport inhibitors: cyenopyrafen, cyflumetofen; O.26 Ryanodine receptor modulators: flubendiamide, chlorantraniliprole, cyantraniliprole, cyclaniliprole, tetraniliprole; (R)-3-chloro-N 1-{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N 2 -(1-Methyl-2-methylsulfonylethyl)phthalamide, (S)-3-chloro-N 1 -{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N 2-(1-Methyl-2-methylsulfonylethyl)phthalamide;Methyl-2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)benzoyl]-1,2-dimethylhydrazinecarboxylate;N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;N-[4-Chloro -2-[(diethyl-lambda-4-sulfanilidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanilidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;N-[4,6-dichloro-2-[(di-2-propyl-lambda-4-sulfanilidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide N-[4,6-dibromo-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide;N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridyl)-1-(trifluoromethyl)pyrazole-3-carboxamide;N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridyl)-1-(trifluoromethyl)pyrazole-3-carboxamide H-Pyrazole-5-carboxamide;3-Chloro-1-(3-chloro-2-pyridinyl)-N-[2,4-dichloro-6-[[(1-cyano-1-methylethyl)amino]carbonyl]phenyl]-1H-pyrazole-5-carboxamide;Tetrachloroanthranilipur;N-[4-Chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide;Cyhalodiamide; O.27: Chordotonal organ modulators - unclear target site: flonicamide; O.28. Insecticidal compounds with unknown or unclear mechanism of action: afidopiropen, afoxolaner, azadirachtin, amidoflumet, benzoximate, brofuranilide, bromopropylate, quinomethionate, cryolite, cyprofuranilide, dichloromezothiaz, dicofol, flufenerim, flometoquin, fluensulfone, fluhexafon, fluopyram, fluralaner, methoxadiazone, piperonyl butoxide, piflubumid, pyridalyl, thioxazaphen, 11-(4-chloro-2,6-dimethyl phenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]-tetradec-11-en-10-one, 3-(4'-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]dec-3-en-2-one, 1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1H-1,2,4-triazol-5-amine, Bacillus firmus firmus) I-1582;Fulpirimine;Fluazaindolizine;4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-(1-oxothiethane-3-yl)benzamide;Fluxamethamide;5-[3-[2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1H-pyrazole;4-Cyano-N-[2-cyano-5-[[2,6-dibromo-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propoxy] 4-cyano-3-[(4-cyano-2-methyl-benzoyl)amino]-N-[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]-2-fluoro-benzamide;N-[5-[[2-chloro-6-cyano-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide;N-[5-[[2-bromo-6-chloro-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide;N-[5-[[2-bromo-6-chloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide;4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1,2,2,3,3, 3-Hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide;4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide;N-[5-[[2-bromo-6-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide 2-(1,3-dioxan-2-yl)-6-[2-(3-pyridinyl)-5-thiazolyl]-pyridine;2-[6-[2-(5-fluoro-3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine;2-[6-[2-(3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine;N-Methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide;N-Methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide;1-[(6-chloro) 1-[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-1,2,3,5,6,7-hexahydro-imidazo[1,2-a]pyridine;1-[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridin-5-ol;1-isopropyl-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;1-(1,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;N,5-Dimethyl-N-pyridazin-4-yl-1-(2,2,2-trifluoro-1-methyl-ethyl)pyrazole-4-carboxamide;1-[1-(1-cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;N-ethyl-1-(2-fluoro-1-methyl-propyl)-5-methyl-N-pyridazin-4-yl-pyrazole-4 -carboxamide;1-(1,2-dimethylpropyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;1-[1-(1-cyanocyclopropyl)ethyl]-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;N-methyl-1-(2-fluoro-1-methyl-propyl)-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide 1-(4,4-difluorocyclohexyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;1-(4,4-difluorocyclohexyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;N-(1-methylethyl)-2-(3-pyridinyl)-2H-indazole-4-carboxamide;N-cyclopropyl-2 -(3-pyridinyl)-2H-indazole-4-carboxamide;N-Cyclohexyl-2-(3-pyridinyl)-2H-indazole-4-carboxamide;2-(3-pyridinyl)-N-(2,2,2-trifluoroethyl)-2H-indazole-4-carboxamide;2-(3-pyridinyl)-N-[(tetrahydro-2-furanyl)methyl]-2H-indazole-5-carboxamide;Methyl 2-[[2-(3-pyridinyl)-2H-indazol-5-yl]carbonyl]hydrazinecarboxylate;N-[(2,2-difluorocyclopropyl)methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide;N-(2,2-difluoropropyl)-2-(3-pyridinyl)-2H-indazole-5-carboxamide;2-(3-pyridinyl)-N-(2-pyrimidinylmethyl)-2H-indazole-5-carboxamide;N-[(5-methyl-2-pyrazinyl)methyl]-2-(3-pyridinyl)-2H-indazole-5-carboxamide, cyclopyrazoflor; Salolaner, Lotilaner, N-[4-chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1-methyl-3-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide; 2-(3-ethylsulfonyl-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-[3-ethylsulfonyl-5-(trifluoromethyl)-2 -pyridyl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine; isocycloceram; N-[4-chloro-3-(cyclopropylcarbamoyl)phenyl]-2-methyl-5-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)pyrazole-3-carboxamide; N-[4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl]-2-methyl-5-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)pyrazole-3-carboxamide; acinonapyr; benzpyrimoxane; tigolaner;Chloro-N-(1-cyanocyclopropyl)-5-[1-[2-methyl-5-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)pyrazol-3-yl]pyrazol-4-yl]benzamide, oxazosulfil, [(2S,3R,4R,5S,6S)-3,5-dimethoxy-6-methyl-4-propoxy-tetrahydropyran-2-yl]-N-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]-carbamate, [(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl]N-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate, [(2S,3R,4R,5S,5 S,6S)-3,5-dimethoxy-6-methyl-4-propoxy-tetrahydropyran-2-yl]-N-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate, [(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl]-N-[4-[ 1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate, (2Z)-3-(2-isopropylphenyl)-2-[(E)-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]methylenehydrazono]thiazolidin-4-one;2-(6-chloro-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-(6-bromo-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-(3-ethylsulfonyl-6-iodo-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5 -b]pyridine, 2-[3-ethylsulfonyl-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-(7-chloro-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-(3-ethylsulfonyl-7-iodo-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine 3-Ethylsulfonyl-6-iodo-2-[3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 3-Ethylsulfonyl-6-iodo-2-[3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridin-2-yl]imidazo[1,2-a]pyridine-8-carbonitrile, 2-[3-Ethylsulfonyl-8-fluoro-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)imidazo-[4,5-b]pyridine, 2-[3-Ethylsulfonyl-7-(trifluoro 2-[3-ethylsulfonyl-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-[3-ethylsulfonyl-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine, 2-(6-bromo-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-6-(trifluoromethyl)pyrazolo[4,3-c]pyridine.

[0236] The active substances referred to as component 2, their preparation and their activity against, for example, harmful fungi are known (see http: / / www.alanwood.net / pesticides / ); these substances are commercially available. The compounds described in the IUPAC nomenclature, their preparation and their pesticidal activity are also known (Can. J. Plant Sci. 48(6), 587-94, 1968; EP-A141 317; EP-A152 031; EP-A226 917; EP-A243 970; EP-A256 503; EP-A428 941; EP-A532 022; EP-A1 028 125; EP-A1 035 122; EP-A1 201 648; EP-A1 122 123). 244;JP 2002-316902;DE 19650197;DE 10021412;DE 102005009458;U.S. Pat. No. 3,296,272;U.S. Pat. No. 3,325,503;WO 98 / 46608;WO 99 / 14187;WO 99 / 24413;WO 99 / 27783;WO 00 / 29404;WO 00 / 46148;WO 00 / 65913;WO 01 / 54501 No.;WO 01 / 56358;WO 02 / 22583;WO 02 / 40431;WO 03 / 10149;WO 03 / 11853;WO 03 / 14103;WO 03 / 16286;WO 03 / 53145;WO 03 / 61388;WO 03 / 66609;WO 03 / 74491;WO 04 / 49804;WO 04 / 83193;WO 05 / 120234;WO 05 / 123689;WO 05 / 123690;WO 05 / 63721;WO 05 / 87772;WO 05 / 87773;WO 06 / 15866;WO 06 / 87325;WO 06 / 87343;WO 07 / 82098;WO 07 / 90624;WO 10 / 13927 WO 11 / 028657;WO 12 / 168188;WO 07 / 006670;WO 11 / 77514;WO 13 / 047749;WO 10 / 069882;WO 13 / 047441;WO 03 / 16303;WO 09 / 90181;WO 13 / 007767;WO 13 / 010862 ;WO 13 / 127704;WO 13 / 024009;WO 13 / 24010;WO 13 / 047441;WO 13 / 162072;WO 13 / 092224;WO 11 / 135833;China Patent No. 1907024;China Patent No. 1456054;China Patent No. 103387541;China Patent No. 1309897;WO 12 / 84812;China Patent No. 1907024;WO 09094442;WO 14 / 60177;WO 13 / 116251;WO 08 / 013622;WO 15 / 65922;WO 94 / 01546;EP 2865265;WO 07 / 129454;WO 12 / 165511;WO 11 / 081174;WO 13 / 47441;(See WO 16 / 156241; WO 16 / 162265). Some compounds are identified by their CAS Registry Number, which consists of three parts, the first consisting of 2 to 7 digits, the second consisting of 2 digits, and the third consisting of 1 digit, separated by hyphens;

[0237] According to the present invention, the solid matter (dry matter) of the biopesticide (excluding oils such as neem oil) is considered as the active ingredient (e.g. obtained after drying or evaporation of the extraction or suspension medium in the case of liquid formulations of microbial pesticides). The weight ratios and percentages used for biological extracts such as Quillay extracts are based on the total weight of the dry content (solid matter) of the respective extract.

[0238] The total weight ratio of the composition containing at least one microbial pesticide in the form of viable microbial cells, including dormant forms, is 1×10 10 The amount of CFU of each microorganism can be determined to calculate the total weight of each active ingredient by the formula: CFU is equal to 1 gram of total weight of each active ingredient. Colony forming units are a measure of viable microbial cells. Furthermore, CFU can be understood as the number of (juvenile) individual nematodes in the case of nematode biopesticides, such as Steinernema feltiae.

[0239] In the binary mixture, the weight ratio of component 1) to component 2) generally depends on the properties of the components used, and it is usually in the range of 1:10,000 to 10,000:1, often 1:100 to 100:1, usually 1:50 to 50:1, preferably 1:20 to 20:1, more preferably 1:10 to 10:1, even more preferably 1:4 to 4:1, in particular 1:2 to 2:1. According to a further embodiment, the weight ratio of component 1) to component 2) is usually in the range of 1000:1 to 1:1, often 100:1 to 1:1, usually 50:1 to 1:1, preferably 20:1 to 1:1, more preferably 10:1 to 1:1, even more preferably 4:1 to 1:1, in particular 2:1 to 1:1. According to a further embodiment, the weight ratio of component 1) to component 2) is usually in the range of 20,000:1 to 1:10, often 10,000:1 to 1:1, usually 5,000:1 to 5:1, preferably 5,000:1 to 10:1, more preferably 2,000:1 to 30:1, even more preferably 2,000:1 to 100:1, in particular 1,000:1 to 100:1. According to a further embodiment, the weight ratio of component 1) to component 2) is usually in the range of 1:1 to 1:1000, often 1:1 to 1:100, usually 1:1 to 1:50, preferably 1:1 to 1:20, more preferably 1:1 to 1:10, even more preferably 1:1 to 1:4, in particular 1:1 to 1:2. According to a further embodiment, the weight ratio of component 1) to component 2) is usually in the range of 10:1 to 1:20,000, often 1:1 to 1:10,000, usually 1:5 to 1:5,000, preferably 1:10 to 1:5,000, more preferably 1:30 to 1:2,000, even more preferably 1:100 to 1:2,000, in particular 1:100 to 1:1,000.

[0240] In ternary mixtures, i.e. compositions comprising components 1) and 2) and compound III (component 3), the weight ratio of components 1) to 2) depends on the properties of the active substances used, and is usually in the range of 1:100 to 100:1, usually 1:50 to 50:1, preferably 1:20 to 20:1, more preferably 1:10 to 10:1, in particular 1:4 to 4:1, and the weight ratio of components 1) to 3) is usually in the range of 1:100 to 100:1, usually 1:50 to 50:1, preferably 1:20 to 20:1, more preferably 1:10 to 10:1, in particular 1:4 to 4:1. Any further active ingredients are added, if necessary, in a ratio of 20:1 to 1:20 relative to component 1). These ratios are also suitable for mixtures applied by seed treatment.

[0241] When mixtures containing microbial pesticides are used for crop protection, the application rate is 1×10 6 ~5×10 16 (or more) CFU / ha, preferably 1 x 10 8 ~1×10 13 CFU / ha, even more preferably 1×10 9 ~5×10 15 CFU / ha, specifically 1 × 10 12 ~5×10 14 CFU / ha. For nematodes (e.g. Steinernema feltiae) as microbial pesticides, application rates are usually in the range of 1×10 per hectare. 5 ~1×10 12 (or more), preferably 1×10 8 ~1×10 11 , more preferably 5 × 10 8 ~1×10 10 A range of individuals (eg in the form of eggs, juveniles or any other live stage, preferably immature juvenile stages).

[0242] When mixtures containing microbial pesticides are used for seed treatment, application rates are generally 1×10 6 ~1×10 12 (or more) CFU / seed, preferably 1 x 10 6 ~1×109 CFU / seed. Furthermore, application rates for seed treatments are generally in the range of 1 x 10 CFU / 100 kg of seed. 7 ~1×10 14 (or more) CFU, preferably 1 x 10 per 100 kg of seeds 9 ~1×10 12 CFU range.

[0243] As component 2), Q in group A o In particular, mixtures comprising at least one active substance selected from (A.1.1), (A.1.4), (A.1.8), (A.1.9), (A.1.13), (A.1.14), (A.1.17), (A.1.21), (A.1.25), (A.1.34) and (A.1.35) are preferred.

[0244] As component 2), Q in group A i In particular, mixtures comprising at least one active substance selected from (A.2.3), (A.2.4) and (A.2.6) are preferred.

[0245] As component 2) there is preferably used the compounds (A.3.2), (A.3.3), (A.3.4), (A.3.7), (A.3.9), (A.3.11), (A.3.12), (A.3.15), (A.3.16), (A.3.17), (A.3.18), (A.3.19), (A.3.20), (A.3.21), (A.3.22), (A.3.23), (A.3.24), (A.3.28), (A.3.31), (A.3.32), (A.3.33), (A.3.34), (A.3.35), (A.3.36), (A.3.7), (A.3.8), (A.3.9), (A.3.10), (A.3.11), (A.3.12), (A.3.15), (A.3.16), (A.3.17), (A.3.18), (A.3.19), (A.3.20), (A.3.21), (A.3.22), (A.3.23), (A.3.24), (A.3.28), (A.3.31), (A.3.32), (A.3.33), (A.3.34), (A.3.35), (A.3.36), (A.3.7), (A.3.7), (A.3.8), (A.3.9), (A.3.10), (A.3.11), (A.3.12), (A.3.13), (A.3.14), (A.3.15), (A.3.16), (A.3.17), (A.3.18), (A.3.19), (A.3.20), (A.3.21), (A.3.22), A.3.37), (A.3.38) and (A.3.39); in particular mixtures comprising at least one active substance selected from (A.3.2), (A.3.3), (A.3.4), (A.3.7), (A.3.9), (A.3.12), (A.3.15), (A.3.17), (A.3.19), (A.3.22), (A.3.23), (A.3.24), (A.3.31), (A.3.32), (A.3.33), (A.3.34), (A.3.35), (A.3.36), (A.3.37), (A.3.38) and (A.3.39) are preferred.

[0246] Preference is also given to mixtures which comprise as component 2) at least one active substance selected from other respiratory inhibitors of group A), more preferably selected from the compounds (A.4.5) and (A.4.11), in particular (A.4.11).

[0247] As component 2), more preferably the compounds (B.1.4), (B.1.5), (B.1.8), (B.1.10), (B.1.11), (B.1.12), (B.1.13), (B.1.17), (B.1.18), (B.1.21), (B.1.22), (B.1.23), (B.1.25), (B.1.26), (B.1.29), (B.1.34), (B.1.37), (B.1.38) selected from the C14 demethylase inhibitors of group B), (B.1.43), (B.1.46), (B.1.53), (B.1.54) and (B.1.55); in particular mixtures comprising at least one active substance selected from (B.1.5), (B.1.8), (B.1.10), (B.1.17), (B.1.22), (B.1.23), (B.1.25), (B.1.33), (B.1.34), (B.1.37), (B.1.38), (B.1.43) and (B.1.46).

[0248] Preference is also given to mixtures which comprise as component 2) at least one active substance selected from the delta 14-reductase inhibitors of group B), more preferably selected from the compounds (B.2.4), (B.2.5), (B.2.6) and (B.2.8); in particular (B.2.4).

[0249] As component 2) there is selected from the phenylamide and acylamino acid fungicides of group C), more preferably from the compounds (C.1.1), (C.1.2), (C.1.4) and (C.1.5); also preferred are mixtures comprising at least one active substance selected in particular from (C.1.1) and (C.1.4).

[0250] Preference is also given to mixtures which comprise as component 2) at least one active substance selected from other nucleic acid synthesis inhibitors of group C), more preferably selected from the compounds (C.2.6), (C.2.7) and (C.2.8).

[0251] As component 2) preference is also given to mixtures which comprise at least one active substance selected from group D), more preferably selected from the compounds (D.1.1), (D.1.2), (D.1.5), (D.2.4) and (D.2.6); in particular selected from (D.1.2), (D.1.5) and (D.2.6).

[0252] Preference is also given to mixtures which comprise as component 2) at least one active substance selected from group E), more preferably selected from the compounds (E.1.1), (E.1.3), (E.2.2) and (E.2.3); in particular (E.1.3).

[0253] Preference is also given to mixtures which comprise as component 2) at least one active substance selected from group F), more preferably selected from the compounds (F.1.2), (F.1.4) and (F.1.5).

[0254] As component 2) there are preferred mixtures comprising at least one active substance selected from group G), more preferably from the compounds (G.3.1), (G.3.3), (G.3.6), (G.5.1), (G.5.3), (G.5.4), (G.5.5), (G.5.6), (G.5.7), (G.5.8), (G.5.9), (G.5.10) and (G.5.11); in particular mixtures comprising at least one active substance selected from (G.3.1), (G.5.1) and (G.5.3).

[0255] As component 2) there are preferred mixtures comprising at least one active substance selected from group H), more preferably selected from the compounds (H.2.2), (H.2.3), (H.2.5), (H.2.7), (H.2.8), (H.3.2), (H.3.4), (H.3.5), (H.4.9) and (H.4.10); in particular selected from (H.2.2), (H.2.5), (H.3.2), (H.4.9) and (H.4.10).

[0256] Preference is also given to mixtures which comprise as component 2) at least one active substance selected from group I), more preferably selected from the compounds (I.2.2) and (I.2.5).

[0257] As component 2) preference is also given to mixtures which contain at least one active substance selected from group J), more preferably selected from the compounds (J.1.2), (J.1.5), (J.1.8), (J.1.11) and (J.1.12); in particular selected from (J.1.5).

[0258] As component 2) preference is also given to mixtures comprising at least one active substance selected from group K), more preferably selected from the compounds (K.1.41), (K.1.42), (K.1.44), (K.1.47), (K.1.57), (K.1.58) and (K.1.59); in particular selected from (K.1.41), (K.1.44), (K.1.47), (K.1.57), (K.1.58) and (K.1.59).

[0259] Biopesticides from groups L1) and / or L2) may also have insecticidal, acaricidal, molluscicidal, pheromone, nematocidal, plant stress relieving, plant growth regulator, plant growth promoting and / or yield increasing activity. Biopesticides from groups L3) and / or L4) may also have fungicidal, bactericidal, virucidal, plant defense active, plant stress relieving, plant growth regulator, plant growth promoting and / or yield increasing activity. Biopesticides from group L5) may also have fungicidal, bactericidal, virucidal, plant defense active, insecticidal, acaricidal, molluscicidal, pheromone and / or nematocidal activity.

[0260] Microbial pesticides, especially those from groups L1), L3) and L5), encompass not only isolated, pure cultures of the respective microorganisms as defined herein, but also cell-free extracts thereof, suspensions thereof in whole broth cultures and metabolite-containing culture media or purified metabolites obtained from whole broth cultures of the microorganisms.

[0261] Many of these biopesticides are deposited under the accession numbers mentioned herein (the prefixes such as ATCC or DSM refer to the acronyms of the respective culture collections, for details see, for example, here: http: / / www.wfcc.info / ccinfo / collection / by_acronym / ), mentioned in the literature, registered and / or commercially available: Aureobasidium pullulans DSM 14940 and DSM 14941 mixture (e.g. blastospores in BlossomProtect® from bio-ferm GmbH, Austria), isolated in 1989 in Konstanz, Germany, Azospirillum brasilense Sp245 (BR 11005; e.g. BASF Agricultural Specialties), originally isolated in the wheat belt (Passo Fundo) of South Brazil at least before 1980, Azospirillum brasilense Sp245 (BR 11005; e.g. BASF Agricultural Specialties), originally isolated in 1989 in Konstanz, Germany, Azospirillum brasilense Sp245 (BR 11005; e.g. BASF Agricultural Specialties), Ltd., Brazil), A. brasilense strains Ab-V5 and Ab-V6 (e.g., in AzoMax from Novozymes BioAg Produtos papra Agricultura Ltda., Quattro Barras, Brazil or Simbiose-Maiz from Simbiose-Agro, Brazil; Plant Soil 331, 413-425, 2010), Bacillus amyloliquefaciens strain AP-188 (NRRL B-50615 and B-50331; U.S. Pat. No. 8,445,255); B. amyloliquefaciens sp. plantarum spp. plantarum (formerly sometimes called B. subtilis, now classified together with B. methylotrophicus and B. velezensis as B. velezensis) (Int. J.Syst. Evol. Microbiol. 66, 1212-1217, 2016): Bassp. plantarum or B. velezensis D747 isolated from the air of Kikugawa City, Japan (US Patent Application Publication No. 20130236522A1; FERM BP-8234; e.g., Double Nickel™ 55 WDG from Certis LLC, USA), Bassp. plantarum or B. velezensis FZB24 isolated from soil in Brandenburg, Germany (also called SB3615; DSM96-2; J. Plant Dis. Prot. 105, 181-197, 1998; e.g., Novozyme plantarum or B. velezensis FZB42 isolated from soil from Brandenburg, Germany (DSM 23117; J. Plant Dis. Prot. 105, 181-197, 1998; e.g., RhizoVital 42 from AbiTEP GmbH, Germany), Bassp. plantarum or B. velezensis MBI600 (also called 1430; NRRL B-50595; U.S. Patent Application Publication No. 2012 / 0149571 A1; e.g., BASF Integral® from Bayer Corp., USA), Bassp. plantarum isolated from a peach orchard in California, USA in 1995 or B. velezensis QST-713 (NRRL B-21661; e.g., Serenade® MAX from Bayer Crop Science LP, USA), Ba subsp. plantarum isolated in South Dakoda, USA in 1992 (B.a.ssp.plantarum) or B.velezensis TJ1000 (also called 1BE; ATCC BAA-390; Canadian Patent Application Publication No. 2471555A1; e.g. QuickRoots™ from TJ Technologies, Watertown, SD, USA), B.firmus CNCM I-1582 (a mutant of the parent strain EIP-N1 (CNCM I-1556) isolated from soil in the central plains of Israel) (WO 2009 / 126473, U.S. Patent No. 6,406,690; e.g. Votivo™ from Bayer CropScience LP, USA), B.pumilus GHA 180 isolated from the rhizosphere of apple trees in Mexico (IDAC 260707-01; e.g. Premier Horticulture, Quebec, Canada), B. pumilus INR-7 (also referred to as BU-F22 and BU-F33), isolated at least before 1993 from cucumber infested with Erwinia tracheiphila (NRRL B-50185, NRRL B-50153; U.S. Pat. No. 8,445,255), B. pumilus KFP9F, isolated at least before 2008 from the rhizosphere of pasture grasses in South Africa (NRRL B-50754; WO 2014 / 029697; e.g., BAC-UP or FUSION-P, BASF Agricultural Specialities (Pty) Ltd., South Africa), B. pumilus QST 2808 was isolated from soil collected in Pohnpei, Federated States of Micronesia in 1998 (NRRL B-30087; e.g., Sonata® or Ballad® Plus from Bayer Crop Science LP, USA), B. simplex (B.simplex ABU 288 (NRRL B-50304; U.S. Pat. No. 8,445,255), B. subtilis FB17 (also called UD 1022 or UD 10-22) isolated from red beet roots in North America (ATCC PTA-11857; System. Appl. Microbiol. 27, 372-379, 2004; U.S. Patent Publication No. 2010 / 0260735; WO 2011 / 109395); B. thuringiensis ssp. aizawai ABTS-1857 (also called ABG-6346; ATCC SD-1372; e.g., BioFa XenTari® from AG, Muensingen, Germany. kurstaki ABTS-351 (ATCC SD-1275; e.g., Dipel® DF from Valent BioSciences, IL, USA), which is identical to HD-1 isolated in 1967 from diseased black cotton bollworms in Brownsville, Texas, USA; Bt subsp. kurstaki SB4 (NRRL B-50753; e.g., Beta Pro® from BASF Agricultural Specialties (Pty) Ltd., South Africa), which was isolated from larval corpses of E. saccharina; Bt subsp. tenebrionis NB-176-1 (a beetle isolated from the brown mealworm, Tenebrio moth); These include B. bassiana GHA (ATCC 74250; e.g., BotaniGard® 22WGP from Laverlam Int. Corp., USA), B. bassiana JW-1 (ATCC 74040; e.g., Naturalis® from CBC (Europe) Srl, Italy), B. bassiana PPRI 5339 (NRRL SRL), isolated from the larvae of the tortoise beetle Conchyloctenia punctata, and B. bassiana PPRI 5339 (NRRL SRL), isolated from the larvae of the tortoise beetle Conchyloctenia punctata. 50757;For example, BASF Agricultural Specialities (Pty) Ltd.BroadBand® from South Africa), the Brazilian Bradyrhizobium elkanii strain SEMIA 5019 (also called 29W) isolated in Rio de Janeiro, Brazil, and SEMIA 587, isolated in 1967 in the state of Rio Grande do Sul and used in commercial inoculants since 1968 from areas where North American isolates were previously inoculated (Appl. Environ. Microbiol. 73(8), 2635, 2007; e.g., GELFIX 5 from BASF Agricultural Specialties Ltd., Brazil), B. japonicum 532c, isolated in the USA from a field in Wisconsin (Nitragin 61A152; Can. J. Plant. Sci. 70, 661-666, 1990; e.g., BASF Agricultural Specialties Ltd., Brazil), Ltd., Canada), the B. japonicum E-109 variant of USDA 138 strain (INTA E109, SEMIA 5085; Eur. J. Soil Biol. 45, 28-35, 2009; Biol. Fertil. Soils 47, 81-89, 2011); the B. japonicum strain deposited at SEMIA and known from Appl. Environ. Microbiol. 73(8), 2635, 2007: SEMIA 5079 (CPAC 15; e.g., BASF Agricultural Specialties), isolated from soil in the Cerrados region of Brazil by Embrapa-Cerrados and used in commercial inoculants since 1992; B. japonicum (GELFIX 5 or ADHERE 60 from B. japonicum Ltd., Brazil), obtained under laboratory conditions by Embrapa-Cerrados in Brazil and used in commercial inoculants since 1992, is a natural variant of SEMIA 586 (CB1809), originally isolated in the USA.japonicum SEMIA 5080 (CPAC7; e.g., GELFIX 5 or ADHERE 60 from BASF Agricultural Specialties Ltd., Brazil); Burkholderia sp. A396 isolated in 2008 from soil in Nikko, Japan (NRRL B-50319; WO 2013 / 032693; Marrone Bio Innovations, Inc., USA), Coniothyrium minitans CON / M / 91-08 isolated from rapeseed (WO 1996 / 021358; DSM 9660; e.g., Contans® WG, Intercept® WG from Bayer CropScience AG, Germany), harpin (alpha-beta) protein (Science 257, 85-88, 1992; e.g., Plant Health Messenger™ or HARP-N Tek from Care plc, UK), Helicoverpa armigera nuclear polyhedrosis virus (HearNPV) (J. Invertebrate Pathol. 107, 112-126, 2011; e.g. Helicovex™ from Adermatt Biocontrol, Switzerland; Diplomata™ from Koppert, Brazil; Vivus™ Max from AgBiTech Pty Ltd., Queensland, Australia), Helicoverpa zea single capsid nuclear polyhedrosis virus (HzSNPV) (e.g. Gemstar™ from Certis LLC, USA), Helicoverpa zea nuclear polyhedrosis virus ABA-NPV-U (e.g. AgBiTech Pty Ltd.Heligen® from BASF Agricultural Specialties Limited, Queensland, Australia), Heterorhabditis bacteriophora (e.g. Nemasys® G from BASF Agricultural Specialities Limited, UK), Isaria fumosorosea Apopka-97 (ATCC 20874; Biocontrol Science Technol. 22(7), 747-761, 2012; e.g. PFR-97™ or PreFeRal® from Certis LLC, USA) isolated from mealybugs on gynura in Apopka, Florida, USA, Metarhizium anisopliae var.anisopliae F52 (also called 275 or V275) (DSM 3884, ATCC 90448; e.g., Met52®, Novozymes Biologicals BioAg Group, Canada), Metschnikowia fructicola 277 isolated from grapevine in central Israel (U.S. Pat. No. 6,994,849; NRRL Y-30752; e.g., Shemer®, formerly Agrogreen, Israel), Paecilomyces ilacinus 251 isolated from infected nematode eggs in the Philippines (AGAL 89 / 030550; WO 1991 / 02051; Crop Protection 27, 352-361, 2008; e.g., Bayer CropScience AG, Germany and MeloCon® from Certis, USA), Paenibacillus alvei NAS6G6 isolated from the rhizosphere of pasture grasses in South Africa at least before 2008 (WO 2014 / 029697; NRRL B-50755; e.g., BAC-UP from BASF Agricultural Specialities (Pty) Ltd., South Africa), Paenibacillus strains isolated from soil samples from various locations in Europe, including Germany: P. epiphyticus Lu17015 (WO 2016 / 020371; DSM 26971), P. polymyxa subsp. plantarum (P. polymyxa ssp. plantarum Lu16774 (WO 2016 / 020371; DSM 26969), Pp subsp. plantarum strain Lu17007 (WO 2016 / 020371; DSM 26970); Illinois, USPasteuria nishizawae Pn1 (ATCC SD-5833; Federal Register 76(22), 5808, February 2, 2011; e.g., Clariva™ PN from Syngenta Crop Protection, LLC, USA), which was isolated from soybean fields in the mid-2000s in A. cerevisiae, Penicillium bilaiae (also called P. bilaii) strains ATCC 18309 (=ATCC 74319), ATCC 20851 and / or ATCC 22348 (=ATCC 74318), originally isolated from soil in Alberta, Canada (Fertilizer Res. 39, 97-103, 1994; Can. J. Plant Res. 20, 1999, 103-111, 1999). Sci. 78(1), 91-102, 1998; U.S. Pat. No. 5,026,417; WO 1995 / 017806; e.g., Jump Start®, Provide® from Novozymes Biologicals BioAg Group, Canada), Reynoutria sachalinensis extract (European Patent No. 0307510B1; e.g., Regalia® SC from Marrone BioInnovations, Davis, CA, USA or Milsana® from BioFa AG, Germany), Steinernema carpocapsae (e.g., Millenium® from BASF Agricultural Specialities Limited, UK), S. feltiae (e.g., BioWorks, Inc.,Nemashield® from BASF Agricultural Specialities Limited, UK; Nemasys® from BASF Agricultural Specialties Limited, UK), Streptomyces microflavus NRRL B-50550 (WO 2014 / 124369; Bayer CropScience, Germany), Trichoderma asperelloides JM41R isolated in South Africa (NRRL 50759; also called T. fertile; e.g., from BASF. Trichoplus® from Agricultural Specialities (Pty) Ltd., South Africa), T. harzianum T-22 (also referred to as KRL-AG2) (ATCC 20847; BioControl 57, 687-696, 2012; e.g., Plantshield® from BioWorks Inc., USA or SabrEx™ from Advanced Biological Marketing Inc., Van Wert, OH, USA).

[0262] According to another embodiment of the mixture, at least one pesticide II is selected from the groups L1) to L5): L1) Microbial pesticides with fungicidal, bactericidal, virucidal and / or plant defense activator activity: Aureobasidium pullulans DSM 14940 and DSM 14941 (L1.1), Bacillus amyloliquefaciens AP-188 (L.1.2), B. amyloliquefaciens ssp. plantarum D747 (L.1.3), B. amyloliquefaciens ssp. plantarum FZB24 (L.1.4), B. amyloliquefaciens ssp.plantarum FZB42 (L.1.5), B. amyloliquefaciens ssp.plantarum MBI600 (L.1.6), B. amyloliquefaciens ssp.plantarum QST-713 (L.1.7), B. amyloliquefaciens ssp.plantarum TJ1000 (L.1.8), B. pumilus GB34 (L.1.9), B. pumilus GHA 180 (L.1.10), B. pumilus INR-7 (L.1.11), B. pumilus KFP9F (L.1.12), B. pumilus QST 2808 (L.1.13), B. simplex ABU 288 (L.1.14), B. subtilis FB17 (L.1.15), Coniothyrium minitans CON / M / 91-08 (L.1.16), Metschnikowia fructicola NRRL Y-30752 (L.1.17), Paenibacillus alvei (L.1.18), alvei) NAS6G6 (L.1.18), P. epiphyticus (P.epiphyticus Lu17015 (L.1.25), P. polymyxa ssp. plantarum Lu16774 (L.1.26), Ppssp. plantarum strain Lu17007 (L.1.27), Penicillium bilaiae ATCC 22348 (L.1.19), P. bilaiae ATCC 20851 (L.1.20), Penicillium bilaiae ATCC 18309 (L.1.21), Streptomyces microflavus NRRL B-50550 (L.1.22), Trichoderma asperelloides JM41R (L.1.23), T. harzianum T-22 (L.1.24);. L2) Biochemical pesticides with fungicidal, bactericidal, virucidal and / or plant defense activator activity: harpin proteins (L.2.1), Reynoutria sachalinensis extract (L.2.2); L3) Microbial pesticides with insecticidal, acaricidal, molluscicidal and / or nematocidal activity: Bacillus firmus I-1582 (L.3.1), B. thuringiensis ssp. aizawai ABTS-1857 (L.3.2), Bt ssp. kurstaki ABTS-351 (L.3.3), Bt ssp. kurstaki SB4 (L.3.4), Bt ssp. tenebrionis NB-176-1 (L.3.5), Beauveria bassiana bassiana GHA (L.3.6), B. bassiana JW-1 (L.3.7), B. bassiana PPRI 5339 (L.3.8), Burkholderia sp. A396 (L.3.9), Helicoverpa armigera nucleopolyhedrovirus (HearNPV) (L.3.10), Helicoverpa zea nucleopolyhedrovirus (HzNPV) ABA-NPV-U (L.3.11), Helicoverpa zea single capsid nucleopolyhedrovirus (HzNPV) ABA-NPV-U (L.3.12), Helicoverpa zea single capsid nucleopolyhedrovirus (HzNPV) ABA-NPV-U (L.3.13), Helicoverpa zea single capsid nucleopolyhedrovirus (HzNPV) ABA-NPV-U (L.3.14), Helicoverpa zea single capsid nucleopolyhedrovirus (HzNPV) ABA-NPV-U (L.3.15), Helicoverpa zea single capsid nucleopolyhedrovirus (HzNPV) ABA-NPV-U (L.3.16), Helicoverpa zea single capsid nucleopolyhedrovirus (HzNPV) ABA-NPV-U (L.3.17), Helicoverpa zea single capsid nucleopolyhedrovirus (HzNPV) ABA-NPV-U (L.3.18), Helicoverpa zea single capsid nucleopolyhedrovirus (HzNPV) ABA-NPV-U (L.3.19), Helicoverpa zea single capsid nucleopolyhedrovirus (HzNPV) ABA-NPV-U (L.3.20), Helicoverpa zea single capsid nucleopolyhedrovirus ( nucleopolyhedrovirus (HzSNPV) (L.3.12), Heterohabditis bacteriophora (L.3.13), Isaria fumosorosea Apopka-97 (L.3.14), Metarhizium anisopliae var. anisopliae F52 (L.3.15), Paecilomyces lilacinus 251 (L.3.16), Pasteuria nishizawae Pn1 (L.3.17), Steinernema carpocapsae (L.3.18), S. feltiae (L.3.19);. L4) Biochemical pesticides with insecticidal, acaricidal, molluscicidal, pheromone and / or nematocidal activity; cis-jasmone (L.4.1), methyl jasmonate (L.4.2), Quillaja extract (L.4.3); L5) Microbial pesticides with plant stress reducing activity, plant growth regulator activity, plant growth promoting activity and / or yield enhancing activity: Azospirillum brasilense Ab-V5 and Ab-V6 (L.5.1), A. brasilense Sp245 (L.5.2), Bradyrhizobium elkanii SEMIA 587 (L.5.3), B. elkanii SEMIA 5019 (L.5.4), B. japonicum 532c (L.5.5), B. japonicum E-109 (L.5.6), B. japonicum SEMIA 5020 (L.5.7), B. japonicum SEMIA 5019 (L.5.8), B. japonicum SEMIA 5019 (L.5.9), B. japonicum SEMIA 5020 (L.5.10), B. japonicum SEMIA 5020 (L.5.11), B. japonicum SEMIA 5020 (L.5.12), B. japonicum SEMIA 5020 (L.5.13), B. japonicum SEMIA 5020 (L.5.14), B. japonicum SEMIA 5020 (L.5.15), B. japonicum SEMIA 5020 (L.5.16), B. japonicum SEMIA 5020 (L.5.17), B. japonicum SEMIA 5020 (L.5.18), B. japonicum SEMIA 5020 (L.5.19), B. japonicum SEMIA 5020 (L.5.19), B. japonicum SEMIA 5020 (L.5.19), B. 5079(L.5.7), B. japonicum SEMIA 5080(L.5.8) is selected from.

[0263] The present invention further relates to an agrochemical composition comprising a mixture of at least one compound I (component 1) and at least one biopesticide selected from group L) (component 2), in particular at least one biopesticide selected from groups L1) and L2), as described above, and optionally at least one suitable adjuvant.

[0264] The present invention further relates to an agrochemical composition comprising a mixture of at least one compound I (component 1) and at least one biopesticide selected from group L), in particular from groups L3) and L4), as described above (component 2), and optionally at least one suitable adjuvant.

[0265] As pesticide II (component 2) there is used a pesticide selected from the groups L1), L3) and L5), preferably (L.1.2), (L.1.3), (L.1.4), (L.1.5), (L.1.6), (L.1.7), (L.1.8), (L.1.10), (L.1.11), (L.1.12), (L.1.13), (L.1.14), (L. 1.15), (L.1.17), (L.1.18), (L.1.19), (L.1.20), (L.1.21), (L.1.25), (L.1.26), (L.1 .27), (L.3.1); (L.3.9), (L.3.16), (L.3.17), (L.5.1), (L.5.2), (L.5.3), (L.5.4), (L. 5.5), (L.5.6), (L.5.7), (L.5.8); (L.4.2) and (L.4.1); even more preferably (L.1.2), (L.1.6), (L.1.7), (L.1.8), (L.1.11), (L.1.12), (L.1.13), (L.1.14), (L.1.15), Also preferred are mixtures comprising a biopesticide selected from (L.1.18), (L.1.19), (L.1.20), (L.1.21), (L.3.1); (L.3.9), (L.3.16), (L.3.17), (L.5.1), (L.5.2), (L.5.5), (L.5.6); (L.4.2) and (L.4.1). These mixtures are particularly suitable for the treatment of propagation material, i.e. for seed treatment purposes, and also for soil treatment. These seed treatment mixtures are particularly suitable for crops such as cereals, corn and legumes such as soybeans.

[0266] As pesticide II (component 2) there is used a pesticide selected from the groups L1), L3) and L5), preferably (L1.1), (L.1.2), (L.1.3), (L.1.6), (L.1.7), (L.1.9), (L.1.11), (L.1.12), (L.1.13), (L.1.14), (L.1.15), (L.1. 17), (L.1.18), (L.1.22), (L.1.23), (L.1.24), (L.1.25), (L.1.26), (L.1.27), (L. 2.2);(L.3.2), (L.3.3), (L.3.4), (L.3.5), (L.3.6), (L.3.7), (L.3.8), (L.3.10), Also preferred are mixtures comprising a biopesticide selected from the strains indicated above as (L.3.11), (L.3.12), (L.3.13), (L.3.14), (L.3.15), (L.3.18), (L.3.19); (L.4.2); even more preferably selected from (L.1.2), (L.1.7), (L.1.11), (L.1.13), (L.1.14), (L.1.15), (L.1.18), (L.1.23), (L.3.3), (L.3.4), (L.3.6), (L.3.7), (L.3.8), (L.3.10), (L.3.11), (L.3.12), (L.3.15), and (L.4.2). These mixtures are particularly suitable for the foliar treatment of cultivated plants, preferably vegetables, fruits, vines, cereals, legumes such as corn and soybeans.

[0267] Compositions containing the mixture of active ingredients can be prepared by conventional means, for example by those given for the compositions of Compound I.

[0268] When live microorganisms form part of the composition, such as pesticides II from groups L1), L3) and L5), such compositions can be prepared by conventional means (e.g. HD Burges: Formulation of Microbial Biopesticides, Springer, 1998; WO 2008 / 002371, U.S. Pat. No. 6,955,912, U.S. Pat. No. 5,422,107). EXAMPLES

[0269] I. Synthesis Examples Example 1-[6-(difluoromethyl)-5-methyl-3-pyridyl]-(3-fluoro-2-nitro-phenyl)methanol A solution of PhMgBr in THF (3M) (1.9 mL, 5.6 mmol) was added dropwise to a solution of 1-fluoro-3-iodo-2-nitrobenzene (1440 mg, 5.3 mmol) in THF (2 mL) at −78° C. under N2. The mixture was stirred at −78° C. for 1 h. Then a solution of 6-(difluoromethyl)-5-methyl-pyridine-3-carbaldehyde (600 mg, 3.5 mmol) in THF (10 mL) was added dropwise to the mixture at −78° C. under N2, and the mixture was stirred at −78° C. for 3 h. The mixture was quenched with ice water (50 mL) and the solution was extracted with EtOAc (15 mL×3). The combined organic layers were successively washed with brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give the title compound as a yellow solid. 1 H NMR (400MHz, DMSO):μ[ppm]:8.41(d,J=1.5Hz,1H),7.74-7.65(m,2H),7.60-7.51(m,1H),7.48 (d,J=7.9Hz,1H),7.16-6.85(m,1H),6.72(d,J=4.8Hz,1H),6.01(d,J=4.6Hz,1H),2.42(s,3H)

[0270] Example 2-(2-amino-3-fluoro-phenyl)-[6-(difluoromethyl)-5-methyl-3-pyridyl]methanol A mixture of [6-(difluoromethyl)-5-methyl-3-pyridyl]-(3-fluoro-2-nitro-phenyl)methanol (550 mg, 16 mmol) and Raney Ni (110 mg) in EtOH (10 mL) was stirred under H2 (15 PSi) at 20°C for 1 h. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was triturated with (PE:EtOAc=10:1) to give the title compound as a yellow solid. 1H NMR (400MHz, CDCl3):μ [ppm]:8.44(s,1H),7.60(s,1H),7.01(ddd,J=1.2,8.2,10.7Hz,1H),6.85-6.55(m,3H),5.94(br s,1H),4.15(br s,2H),2.88(br d,J=3.5Hz,1H),2.51(s,3H)

[0271] Example 3-(2-amino-3-fluoro-phenyl)-[6-(difluoromethyl)-5-methyl-3-pyridyl]methanone To a solution of (2-amino-3-fluoro-phenyl)-[6-(difluoromethyl)-5-methyl-3-pyridyl]methanol (450 mg, 1.6 mmol) in 10 mL of ethyl acetate was added K2CO3 (442 mg, 3.2 mmol) and CuCl (31 mg, 0.32 mmol) at 20 °C, and the mixture was stirred at 65 °C under O2 (15 PSi) for 16 h. The mixture was poured into ice water (30 mL) and filtered. The filtrate was extracted with EtOAc (30 mL x 3), washed with brine (15 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuum. The crude product was purified by liquid chromatography on silica gel (PE: EtOAc = 5: 1) to give the title compound as a yellow oil. 1 H NMR (400MHz, CDCl3):μ[ppm]:8.65(s,1H),7.85(s,1H),7.23-7.16(m,2H),6.90-6.61(m,1H),6.58(dt,J=4.9,8.0Hz,1H),6.29(br s,2H),2.60(s,3H)

[0272] Example 4 - 4-[6-(difluoromethyl)-5-methyl-3-pyridyl]-8-fluoro-2,2-dimethyl-1H-quinazoline A mixture of (2-amino-3-fluoro-phenyl)-[6-(difluoromethyl)-5-methyl-3-pyridyl]methanone (200 mg, 0.7 mmol) and NHOAc (539 mg, 7.0 mmol) in acetone (7 mL) was stirred at 65° C. for 4 h. The mixture was poured into ice water (15 mL), extracted with EtOAc (10 mL×3), washed with brine (15 mL), dried over anhydrous magnesium sulfate, and concentrated in vacuo. The crude product was purified by liquid chromatography on silica gel (PE:EtOAc=3:1) to give the title compound as a yellow solid. 1 H NMR (400MHz, CDCl3):μ [ppm]:8.55(s,1H),7.77(s,1H),7.08(ddd,J=1.1,8.2,10.4Hz,1H),6.93-6.52(m,3H),4.25(br s,1H),2.57(s,3H),1.60(s,6H)

[0273] The compounds listed in Table I were prepared in an analogous manner.

[0274] Table I:R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and the meaning of Xn is as defined in each row. Compounds Ex-1 to Ex-7 of formula I. *HPLC: high performance liquid chromatography; HPLC column Kinetex XB C18 1.7μ (50×2.1 mm); eluent: acetonitrile / water + 0.1% trifluoroacetic acid (gradient from 5:95 to 100:0 in 1.5 min at 60° C., flow rate gradient 0.8 to 1.0 ml / min in 1.5 min). R t : Retention time in minutes [ka]

[0275] [Table 17]

[0276]

Table 18

[0277]

Table 19

[0278]

Table 20

[0279]

Table 21

[0280]

Table 22

[0281]

Table 23

[0282]

Table 24

[0283]

Table 25

[0284]

Table 26

[0285]

Table 27

[0286]

Table 28

[0287]

Table 29

[0288]

Table 30

[0289]

Table 31

[0290]

Table 32

[0291]

Table 33

[0292]

Table 34

[0293]

Table 35

[0294]

Table 36

[0295]

Table 37

[0296] [Table 38]

[0297] [Table 39]

[0298] [Table 40]

[0299] greenhouse Compounds were dissolved in a mixture of acetone and / or dimethylsulfoxide and Wettol, an ethoxylated alkylphenol-based wetting agent / emulsifier, in a solvent-emulsifier ratio of 99 to 1 (by volume) to a total volume of 5 ml, then water was added to a total volume of 100 ml.

[0300] This stock solution was then diluted with the indicated solvent-emulsifier-water mixture to the final concentrations shown in the table below.

[0301] Example 1 - Preventive fungicidal control of Botrytis cinerea on pepper leaves Bell pepper seedlings were grown in pots until the 4-5 leaf stage. The plants were sprayed to runoff with the spray solutions described above, containing the concentrates of the active ingredients or mixtures listed in the table below. The next day the plants were inoculated with an aqueous biomalt solution or a DOB solution containing a spore suspension of Botrytis cinerea. The plants were then immediately transferred to a humid chamber. After 5 days at 22-24°C and saturated relative humidity, the extent of fungal attack on the leaves was visually assessed as % diseased leaf area.

[0302] In this test, untreated plants were 80% infected, whereas Examples Ex-2, Ex-6, Ex-7, Ex-9, Ex-11, Ex-13, Ex-14, Ex-15, Ex-19, Ex-21, Ex-22, Ex-23, Ex-27, Ex-28, Ex-29, Ex-30, Ex-32, Ex-33, Ex-34, Ex-35, Ex-36, Ex-38, Ex-39, Ex-40, Ex-41, Ex-43, Ex-45, Ex-46, Ex-53, Ex-54, Ex-55, Ex-56 Samples treated with 250 ppm of active substances from Ex-60, Ex-61, Ex-62, Ex-63, Ex-89, Ex-107, Ex-115, Ex-116, Ex-125, Ex-130, Ex-134, Ex-141, Ex-142, Ex-144, Ex-145, Ex-146, Ex-147, Ex-148, Ex-149, Ex-152, Ex-158, Ex-161, Ex-164, Ex-165, Ex-167, respectively, showed a maximum growth of 15% or less of the pathogen.

[0303] Example 2 - Preventive fungicidal control of rapeseed white mold disease caused by Sclerotinia sclerotiorum SCLESC P1 OSR Rapeseed plants were grown in pots to the 13-14 leaf stage. The plants were sprayed to runoff with the spray solutions described above, containing the concentrates of the active ingredients or mixtures thereof listed in the table below.

[0304] Plants were allowed to air dry. The next day, applied rapeseed petals were fixed with 25 μl of 2.5% methylcellulose on the leaves and 1 and 2.25 μl of Sclerotinia sclerotiorum spore suspensions were pipetted onto each fixed rapeseed petal. After 14 days at 20 °C and 60% relative humidity, the extent of fungal attack on the leaves was visually assessed as % diseased leaf area.

[0305] In this test, untreated plants were 80% infected, whereas samples treated with 100 g / ha of active substance from examples Ex-6, Ex-9, Ex-19, Ex-22, Ex-27, Ex-30, Ex-32, Ex-33, Ex-45, Ex-53, Ex-60, Ex-80, Ex-81 each showed a maximum pathogen growth of 13% or less.

[0306] Example 3 - Preventive fungicidal control of soybean white mold disease caused by Sclerotinia sclerotiorum (SCLESC P1) Soybean seedlings were grown in pots. The plants were sprayed to runoff with the spray solutions described above, containing the concentrates of the active ingredients or mixtures listed in the table below. The next day, the treated plants were inoculated with a biomalt suspension containing mycelium of Sclerotinia sclerotiorum. The trial plants were then cultivated for 6 days in a greenhouse at 23°C and relative humidity of 80 and 85%. The extent of fungal attack on the leaves was visually assessed as % diseased leaf area.

[0307] In this test, untreated plants were 80% infected, whereas samples treated with 250 ppm of active substance from examples Ex-6, Ex-7, Ex-9, Ex-13, Ex-14, Ex-15, Ex-19, Ex-27, Ex-29, Ex-32, Ex-33, Ex-45, Ex-53, Ex-60, Ex-80, Ex-81, Ex-91, Ex-116, Ex-134, Ex-141, Ex-158, Ex-170, respectively, showed a maximum pathogen growth of 21% or less.

[0308] Micro Test The active compounds were formulated separately as stock solutions having a concentration of 10,000 ppm in dimethylsulfoxide.

[0309] The stock solutions were mixed according to ratio, pipetted onto microtiter plates (MTPs) and diluted to the stated concentrations with water.

[0310] Example 1 - Activity against Botrytis cinerea in a microtiter plate test A spore suspension of Botruci cinerea in a biomalt solution or a yeast-bactopeptone-sodium acetate solution was then added.

[0311] In this test, Examples Ex-1, Ex-2, Ex-3, Ex-4, Ex-5, Ex-6, Ex-7, Ex-8, Ex-9, Ex-11, Ex-13, Ex-14, Ex-15, Ex-16, Ex-17, Ex-19, Ex-20, Ex-21, Ex-22, Ex-23, Ex-24, Ex-25, Ex-26, Ex-27, Ex-28, Ex-29, Ex-30, Ex-31, Ex-32, Ex-33, Ex-34, Ex-35, Ex-36, Ex-37, Ex-38, Ex-39, Ex-40, Ex-41,Ex-42, Ex-43, Ex-44, Ex-45, Ex-46, Ex-47, Ex-48, Ex-49, Ex-50, Ex-51, Ex-52, Ex-53, Ex-54, Ex-55, Ex-56, Ex-57, Ex-58, Ex-5 9, Ex-60, Ex-61, Ex-62, Ex-63, Ex-64, Ex-65, Ex-66, Ex-67, Ex-68, Ex-69, Ex-70, Ex-71, Ex-72, Ex-73, Ex-74, Ex-75, Ex-76, Ex -77, Ex-79, Ex-80, Ex-81, Ex-83, Ex-84, Ex-84, Ex-85, Ex-86, Ex-87, Ex-88, Ex-89, Ex-90, Ex-91, Ex-92, Ex-93, Ex-94, Ex-95, Ex-96, Ex-97, Ex-98, Ex-99, Ex-100, Ex-101, Ex-102, Ex-103, Ex-104, Ex-105, Ex-106, Ex-107, Ex-109, Ex-110, Ex-111, Ex-11 2, Ex-113, Ex-114, Ex-115, Ex-116, Ex-117, Ex-118, Ex-119, Ex-120, Ex-121, Ex-122, Ex-123, Ex-125, Ex-127, Ex-128, Ex-129 , Ex-130, Ex-131, Ex-132, Ex-133, Ex-134, Ex-135, Ex-136, Ex-137, Ex-139, Ex-141, Ex-142, Ex-143, Ex-144, Ex-145, Ex-146, Samples treated with 31 ppm of active substances from Ex-147, Ex-148, Ex-149, Ex-150, Ex-151, Ex-152, Ex-153, Ex-154, Ex-157, Ex-158, Ex-159, Ex-160, Ex-161, Ex-162, Ex-163, Ex-164, Ex-165, Ex-166, Ex-167, Ex-168, Ex-169, Ex-170, Ex-171, Ex-172, respectively, showed less than 14% pathogen growth.

[0312] Example 2 - Activity against Fusarium culmorum in a microtiter plate test A spore suspension of Fusarium culmorum in an aqueous biomalt solution or in an aqueous yeast-bactopeptone-glycerol or DOB solution was then added.

[0313] In this test, the examples Ex-2, Ex-3, Ex-4, Ex-6, Ex-9, Ex-13, Ex-16, Ex-19, Ex-20, Ex-22, Ex-23, Ex-27, Ex-29, Ex-32, Ex-33, Ex-34, Ex-35, Ex-36, Ex-38, Ex-40, Ex-46, Ex-47, Ex-50, Ex-53, Ex-55, Ex-59, Ex-60, Ex-63, Ex-65, Ex-66, Ex-67, Ex-75, Ex-77, Ex-81, Ex-89, Ex-91, Ex-93, Ex-101, Ex Samples treated with 31 ppm of active substances from Ex-102, Ex-103, Ex-104, Ex-105, Ex-106, Ex-107, Ex-114, Ex-117, Ex-121, Ex-122, Ex-123, Ex-125, Ex-132, Ex-134, Ex-135, Ex-137, Ex-145, Ex-147, Ex-148, Ex-149, Ex-151, Ex-160, Ex-164, Ex-165, Ex-166, Ex-167, Ex-170, Ex-172, respectively, showed less than 20% pathogen growth.

[0314] Example 3 - Activity against wheat leaf spot caused by Septoria tritici A spore suspension of Septoria tritici in an aqueous biomalt solution or in an aqueous yeast-bactopeptone-glycerol or DOB solution was then added.

[0315] In this test, Examples Ex-3, Ex-9, Ex-14, Ex-19, Ex-22, Ex-29, Ex-32, Ex-38, Ex-50, Ex-53, Ex-56, Ex-62, Ex-63, Ex-64, Ex-65, Ex-66, Ex-68, Ex-69, Ex-70, Ex-71, Ex-73, Ex-74, Ex-75, Ex-76, Ex-77, Ex-81, Ex-87, Ex-91, Ex-92, Ex-93, Ex-94, Ex-97, Ex-101, Ex-102, Ex-10 Samples treated with 31 ppm of active substances from Ex-105, Ex-106, Ex-113, Ex-115, Ex-118, Ex-123, Ex-125, Ex-127, Ex-129, Ex-130, Ex-132, Ex-137, Ex-141, Ex-142, Ex-145, Ex-147, Ex-158, Ex-161, Ex-164, Ex-165, Ex-166, Ex-167, Ex-168, Ex-169, Ex-170, respectively, showed less than 20% pathogen growth.

[0316] The measured parameters were compared to the growth of a control variant without active compound (100%) and a blank value without fungus to determine the relative growth in % of the pathogen for each active compound.

[0317] Example 4 - Activity against Botrytis cinerea and Pyricularia oryzae in a microtiter plate test A spore suspension of Pyricularia oryzae in an aqueous biomalt solution or in an aqueous yeast-bactopeptone-sodium acetate solution was then added.

[0318] In this test, samples treated with 31 ppm of active substance from examples Ex-1, Ex-2, Ex-3, Ex-4, Ex-5, Ex-6, Ex-7, Ex-8, Ex-9, Ex-13, Ex-14, Ex-16, Ex-19, Ex-21, Ex-22, Ex-23, Ex-25, Ex-26, Ex-27, Ex-28, Ex-29, Ex-30, Ex-31, Ex-33, Ex-36, Ex-37, Ex-38, Ex-40, Ex-41, Ex-42, Ex-44, respectively, showed less than 20% pathogen growth.

[0319] Example 5 - Activity against the grey mold fungus Cercospora beticula in a microtiter plate test A spore suspension of Cercospora beticula in an aqueous biomalt solution or in a yeast-bactopeptone-sodium acetate solution was then added.

[0320] In this test, samples treated with 31 ppm of active material from Examples Ex-9, Ex-22, Ex-32, Ex-50, Ex-53, Ex-56, and Ex-60 each showed less than 17% pathogen growth.

[0321] Example 6 - Activity against the gray mold fungus Cercospora sojina in a microtiter plate test A spore suspension of Cercospora sojina in an aqueous biomalt solution or in an aqueous yeast-bactopeptone-sodium acetate solution was then added.

[0322] In this test, samples treated with 31 ppm of active material from Examples Ex-6, Ex-9, Ex-22, Ex-23, Ex-28, Ex-29, and Ex-32 each showed 17% or less pathogen growth.

[0323] Example 7 - Activity against the grey mold fungus Cercospora zeae maydis in a microtiter plate test A spore suspension of Cercospora zeae maydis in aqueous biomalt or yeast-bactopeptone-sodium acetate solution was then added.

[0324] In this test, samples treated with 31 ppm of active substance from Examples Ex-5, Ex-6, Ex-9, Ex-22, Ex-29, Ex-38, Ex-41, Ex-50, Ex-53, Ex-56, Ex-60, Ex-61, Ex-81, Ex-91, respectively, showed 17% pathogen growth.

[0325] Example 8 - Activity against the gray mold fungus Corynespora cassiicola G413A mutant in a microtiter plate assay A spore suspension of Corynespora cassiicola in aqueous biomalt or in aqueous yeast-bactopeptone-sodium acetate solution was then added.

[0326] In this test, samples treated with 31 ppm of active substance from examples Ex-5, Ex-6, Ex-7, Ex-8, Ex-9, Ex-13, Ex-14, Ex-15, Ex-20, Ex-22, Ex-23, Ex-25, Ex-26, Ex-27, Ex-28, Ex-29, Ex-31, Ex-32, Ex-35, Ex-36, Ex-38, Ex-40, Ex-41, Ex-50, Ex-53, Ex-55, Ex-56, Ex-60, Ex-61, Ex-91, respectively, showed a pathogen growth of 19%.

Claims

1. Compound of formula I as a fungicide 【Chemical 1】 [wherein, R １ is H, halogen, CN, C １ ~C ４ alkyl, C １ ~C ４ haloalkyl; R ２ is independently selected in each case from halogen, CN, C １ to C ６ alkyl, C １ to C ６ haloalkyl, C ２ to C ６ alkenyl, C ２ to C ６ haloalkenyl, C ２ to C ６ alkynyl, C ２ to C ６ haloalkynyl, O-C １ to C ６ alkyl, O-C ２ to C ６ alkenyl, O-C ２ to C ６ alkynyl, C ３ to C ６ cycloalkyl; R ３ is independently selected in each case from halogen, CN, C １ to C ６ alkyl, C １ to C ６ haloalkyl, C ２ to C ６ alkenyl, C ２ to C ６ haloalkenyl, C ２ to C ６ alkynyl, C ２ to C ６ haloalkynyl, O-C １ to C ６ alkyl, O-C ２ to C ６ alkenyl, O-C ２ to C ６ alkynyl, C ３ to C ６ cycloalkyl; R ４ is H, halogen, CN, C １ to C ４ alkyl, C １ to C ４ haloalkyl; R ５ is, in each case, independently selected from halogen, CN, C １ to C ６ alkyl, C １ to C ６ haloalkyl, C ２ to C ６ alkenyl, C ２ to C ６ haloalkenyl, C ２ to C ６ alkynyl, C ２ to C ６ haloalkynyl, phenyl, benzyl; Here, R ５ The phenyl and benzyl moieties of which are unsubstituted or substituted by 1 to 3 groups R ５ａ and these groups are, independently of one another, Halogen, CN, C １ ~C ６ alkyl, C １ ~C ６ haloalkyl, O-C １ ~C ６ selected from alkyl; R ６ is, in each case, independently selected from halogen, CN, C １ to C ６ alkyl, C １ to C ６ haloalkyl, C ２ to C ６ alkenyl, C ２ to C ６ haloalkenyl, C ２ to C ６ alkynyl, C ２ to C ６ haloalkynyl, phenyl, benzyl; Here, R ６ 's phenyl and benzyl moieties are unsubstituted or substituted by 1 to 3 groups R ６ａ and these groups are, independently of one another, Halogen, CN, C １ ~C ６ alkyl, C １ ~C ６ haloalkyl, O-C １ ~C ６ selected from; or R ５ and R ６ together with the C atom to which they are attached form a C ３ -C ６ cycloalkyl, or a 3- to 6-membered saturated heterocycle containing 1, 2 or 3 heteroatoms from the group consisting of O and S; R ７ is, in each case, hydrogen, CN, CH ２ CN, CH(CH ３ ), CN, CH(=O), C(=O)C １ ~C ６ alkyl, C(=O)C ２ ~C ６ alkenyl, C(=O)C ２ ~C ６ alkynyl, C(=O)C ３ ~C ６ cycloalkyl, C(=O)NH-C １ ~C ４ alkyl, C(=O)N-(C １ ~C ４ alkyl) ２、 C １ ~C ６ alkyl, O-C １ ~C ６ alkyl, C １ ~C ４ haloalkyl, C ３ ~C ６ cycloalkyl, C ３ ~C ６ halocycloalkyl, C ２ ~C ６ alkenyl, C ２ ~C ６ haloalkenyl, C ２ ~C ６ alkynyl, C ２ ~C ６ haloalkynyl, -S(=O) ２ -R ７ａ , 5- or 6-membered heteroaryl and aryl or benzyl, independently selected; where the heteroaryl contains 1, 2 or 3 heteroatoms selected from N, O and S; where the aryl and benzyl groups are unsubstituted or are substituted with CN, halogen, OH, C １ ~C ４ alkyl, C １ ~C ４ haloalkyl, C １ ~C ４ alkoxy and C １ ~C ４ having 1, 2, 3, 4 or 5 substituents selected from the group consisting of halogen alkoxy; wherein, R ７ａ is C １ to C ６ alkyl, C １ to C ６ haloalkyl, C ２ to C ６ alkenyl, C ２ to C ６ haloalkenyl, C ２ to C ６ alkynyl, C ２ to C ６ haloalkynyl, phenyl, benzyl, where phenyl and benzyl are unsubstituted or substituted by halogen, C １ to C ６ alkyl, C １ to C ６ haloalkyl, C ２ to C ６ alkenyl, C ２ to C ６ haloalkenyl, C ２ to C ６ alkynyl, C ２ to C ６ haloalkynyl and can be substituted; X is, in each case, independently selected from halogen, CN, C １ to C ６ alkyl, C １ to C ６ haloalkyl, O-C １ to C ６ alkyl, O-C １ to C ６ haloalkyl; n is 0, 1, 2 or 3] and its N-oxides and agriculturally acceptable salts.

2. R ２ is C １ to C ６ alkyl, the compound according to claim 1.

3. R ２ is CH ３ and is the compound according to claim 1.

4. R ３ is C １ to C ６ alkyl, C １ to C ６ The compound according to claim 1, selected from haloalkyls.

5. R ３ is CH ３ or CHF ２ and is the compound according to claim 1.

6. R ５ is C １ to C ６ alkyl, the compound according to claim 1.

7. R ６ is selected from the group consisting of the C １ -C ６ alkyl, phenyl, and benzyl, and the phenyl and benzyl moieties of R ５ are unsubstituted or substituted by 1 to 3 groups R ５ａ which are, independently of one another, Halogen, CN, C １ ~C ６ alkyl, C １ ~C ６ haloalkyl, O-C １ ~C ６ The compound according to claim 1, selected from halogen, CN, C~C alkyl, C~C haloalkyl, O-C~C alkyl.

8. R ５ and R ６ together with the C atom to which they are attached form a C ３ -C ６ -cycloalkyl, the compound according to claim 1.

9. X is halogen, C １ ~C ６ alkyl, O-C １ ~C ６ alkyl, O-C １ ~C ６ The compound according to claim 1, selected from halogenoalkyls.

10. X is F, CH ３ , C ２ H ５ , OCH ３ , OCHF ２ , OCF ３ The compound according to claim 1, selected from

11. R ７ is H, CN, C(=O)C １ ~C ６ alkyl, C １ ~C ６ alkyl, S(=O) ２ -R ７ａ The compound according to claim 1, selected from

12. A composition comprising one compound of formula I, its N-oxide or an agriculturally acceptable salt as defined in claim 1.

13. A method for controlling phytopathogenic fungi, comprising treating a material, plant, soil or seed to be protected from said fungi or fungal attack with an effective amount of at least one compound of formula I as defined in any one of claims 1 to 11 or with a composition as defined in any one of claims 12.

14. Seeds coated with an amount of 0.1 to of at least one compound of formula I as defined in any one of claims 1 to 11 or its agriculturally acceptable salt or with a composition as defined in any one of claims 12.

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