Novel substituted tetrahydrobenzoxazines

Abstract

The invention relates to compounds of formula (I), wherein the variables are as defined in the description and in the claims. The invention further relates to their uses and compositions. # imgabs0 #

Description

[0001] The present invention relates to novel tetrahydrobenzoxazepines as fungicides The invention also relates to a composition comprising at least one compound I, a method for combating phytopathogenic fungi, and seeds coated with at least one compound of formula I.

[0002] US20110136782 discloses some tetrahydrobenzoxazepines Compounds. However, in many cases, especially at low application rates, the fungicidal activity of the known compounds is not satisfactory. Based on this, one object of the present invention is to provide compounds with improved activity and / or a broader spectrum of activity against phytopathogenic fungi. Another object of the present invention is to provide fungicides with improved toxicological properties or with improved environmental fate properties.

[0003] These and further objects are achieved by the tetrahydrobenzoxazepine having the formula (I) as defined below Compounds and agriculturally suitable implementations thereof.

[0004] Therefore, the present invention relates to a compound having formula I or an N-oxide, tautomer, stereoisomer or agriculturally acceptable salt thereof

[0005]

[0006] in

[0007] R 1 is independently selected at each occurrence from H, halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl;

[0008] R 2 is independently selected at each occurrence from halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, O-C1-C6-alkyl, O-C2-C6-alkenyl, O-C2-C6-alkynyl, C3-C6-cycloalkyl, S-C1-C6-alkyl, S-C2-C6-alkenyl, S-C2-C6-alkynyl;

[0009] R 3independently selected in each case from halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, O-C1-C6-alkyl, O-C2-C6-alkenyl, O-C2-C6-alkynyl, C3-C6-cycloalkyl, S-C1-C6-alkyl, S-C2-C6-alkenyl, S-C2-C6-alkynyl; and

[0010] R 4 independently selected in each case from H, halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl;

[0011] R 5 independently selected in each case from hydrogen, halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, benzyl, a five- or six-membered heteroaryl or a five- or six-membered CH2-heteroaryl; where the heteroaryl contains one, two or three heteroatoms selected from N, O and S; and where these aliphatic or aromatic groups are unsubstituted or carry 1, 2 or 3 substituents R 5a ; where

[0012] each R 5a is independently halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl or O-C1-C6-alkyl;

[0013] R 6 independently selected in each case from hydrogen, halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, benzyl, a five- or six-membered heteroaryl or a five- or six-membered CH2-heteroaryl; where the heteroaryl contains one, two or three heteroatoms selected from N, O and S; and where these aliphatic or aromatic groups are unsubstituted or carry 1, 2 or 3 substituents R 6a ; where

[0014] each R 6a is independently halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl or O-C1-C6-alkyl;

[0015] or

[0016] R 5 and R 6 together form an oxo group (=O); or a thio group (=S);

[0017] or

[0018] R 5 and R 6 together with the carbon atom to which they are bonded form a 3-, 4-, 5- or 6-membered saturated carbon ring or a 3-, 4-, 5- or 6-membered saturated heterocyclic ring containing 1, 2 or 3 heteroatoms selected from O and S as ring members; wherein the carbon ring or heterocyclic ring is unsubstituted or bears 1, 2 or 3 substituents R 56 wherein

[0019] each R 56 independently is halogen, C1-C6-alkyl or C1-C6-haloalkyl;

[0020] R 7 in each case independently is selected from hydrogen, halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, benzyl, a five- or six-membered heteroaryl or a five- or six-membered CH2-heteroaryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; and wherein these aliphatic or aromatic groups are unsubstituted or bear 1, 2 or 3 substituents R 7a wherein

[0021] each R 7a independently is halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl or O-C1-C6-alkyl;

[0022] R 8 in each case independently is selected from hydrogen, halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, benzyl, a five- or six-membered heteroaryl or a five- or six-membered CH2-heteroaryl; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; and wherein these aliphatic or aromatic groups are unsubstituted or bear 1, 2 or 3 substituents R 8a wherein

[0023] each R 8a independently is halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl or O-C1-C6-alkyl;

[0024] or

[0025] R 7 and R 8 together form an oxo group (=O) or a thio group (=S);

[0026] or

[0027] R7 and R 8 together with the carbon atom to which they are bonded form a 3-, 4-, 5- or 6-membered saturated carbon ring or a 3-, 4-, 5- or 6-membered saturated heterocyclic ring containing 1, 2 or 3 heteroatoms selected from O and S as ring members;

[0028] R 9 is independently selected in each case from H, 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)-N(H)C1-C4-alkyl, -C(=O)-N(C1-C4-alkyl)2, C1-C6-alkyl, C1-C6-alkoxy, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, -S(=O)2-R 9a , a five- or six-membered heteroaryl, aryl or benzyl; wherein the heteroaryl contains 1, 2 or 3 heteroatoms selected from N, O and S as ring members; wherein the benzene rings in the aryl and benzyl are unsubstituted or carry 1, 2, 3, 4 or 5 substituents selected from the group consisting of: CN, halogen, OH, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy; wherein the benzene ring in the benzyl is unsubstituted or carries 1, 2 or 3 substituents selected from the group consisting of: CN and halogen;

[0029] wherein

[0030] R 9a is C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl or benzyl, wherein the benzene rings in the last two mentioned groups are unsubstituted or carry 1, 2 or 3 substituents each independently selected from the group consisting of: halogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl and C2-C6-haloalkynyl;

[0031] X is independently selected in each case from halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy, phenyl, benzyl, phenoxy, benzyloxy, C1-C6-thioalkyl;

[0032] n is 0, 1, 2 or 3,

[0033] Provided that

[0034] R 5 、R 6 、R 7 、R 8 cannot all be H.

[0035] The N-oxides can be prepared from the compounds of the invention according to conventional oxidation methods, for example by treatment with an organic peracid such as meta-chloroperbenzoic acid (see WO 03 / 64572 or J. Med. Chem. [Journal of Medicinal Chemistry] 38(11), 1892 - 903, 1995); or with an inorganic oxidizing agent such as hydrogen peroxide (see J. Heterocyc. Chem. [Journal of Heterocyclic Chemistry] 18(7), 1305 - 8, 1981) or potassium peroxymonosulfate preparation (see J. Am. Chem. Soc. [Journal of the American Chemical Society] 123(25), 5962 - 5973, 2001) of compound I. The oxidation can yield the pure mono-N-oxide or a mixture of different N-oxides, which can be separated by conventional methods such as chromatography.

[0036] The agriculturally acceptable salts of the compounds of formula I particularly encompass salts of cations or acid addition salts of acids, where these cations and anions respectively have no adverse effect on the fungicidal action of compound I. Accordingly, suitable cations are in particular alkali metal (preferably sodium and potassium) ions, alkaline earth metal (preferably calcium, magnesium and barium) ions, transition metal (preferably manganese, copper, zinc and iron) ions, and also the ammonium ion, which, if desired, can be substituted by one to four C1 - C4-alkyl substituents and / or one phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, and furthermore phosphonium ions, sulfonium ions, preferably tri(C1 - C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(C1 - C4-alkyl)sulfoxonium.

[0037] The anions of the acceptable acid addition salts are mainly chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the 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.

[0038] Compounds having formula I may exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers resulting from restricted rotation about a single bond of an asymmetric group, and geometric isomers. They also form part of the subject matter of the present invention. Those skilled in the art will understand that a stereoisomer may be more active and / or may exhibit beneficial effects when enriched relative to one or more other stereoisomers, or when separated from one or more other stereoisomers. In addition, those skilled in the art know how to separate, enrich, and / or selectively prepare the stereoisomers. The compounds of the present invention may exist as mixtures of stereoisomers (e.g., racemates), individual stereoisomers, or as optically active forms.

[0039] Compounds having formula I may exist in different crystalline modifications, the biological activities of which may be different. They also form part of the subject matter of the present invention.

[0040] With regard to the variables, examples of the intermediates obtained during the preparation of compound I correspond to the examples of the compounds having formula I. The term "compound I" refers to the compounds having formula I.

[0041] Hereinafter, the intermediate compounds are further described. Those skilled in the art will readily understand that the preferred options of the substituents given herein in connection with compound I, and in particular the preferred options given in the following table for the respective substituents, apply correspondingly to the intermediates. Thus, the substituents in each case have the meanings as defined herein, independently of one another or more preferably in combination.

[0042] If the synthesis yields a mixture of isomers, separation is generally not necessarily required, since in some cases the individual isomers may interconvert during the work-up for use or during administration (e.g., under the action of light, acids or bases). Such conversions may also occur after use, for example in the treated plant in the case of plant treatment, or in the harmful fungi to be controlled.

[0043] In the definitions of the variables given above, collective terms are used which generally represent the substituents in question. The term "C n -C m " indicates the possible number of carbon atoms in the substituent or substituent part in question in each case.

[0044] The term "halogen" refers to fluorine, chlorine, bromine and iodine.

[0045] The term "C1-C6-alkyl" refers to a straight-chain or branched-chain 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-chain or branched-chain alkyl group having 2 to 4 carbon atoms, such as ethyl, propyl (n-propyl), 1-methylethyl (isopropyl), butyl, 1-methylpropyl (sec-butyl), 2-methylpropyl (isobutyl), 1,1-dimethylethyl (tert-butyl).

[0046] The term "C1-C6-haloalkyl" refers to an alkyl group having 1 or 6 carbon atoms as defined above, where some or all of the hydrogen atoms in these groups can be replaced by halogen atoms as described above. Examples are "C1-C2-haloalkyl" 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.

[0047] The term "C2-C6-alkenyl" refers to a straight-chain or branched-chain unsaturated hydrocarbon group having 2 to 6 carbon atoms and having a double bond at any position. Examples are "C2-C4-alkenyl" groups such as vinyl, 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.

[0048] The term "C2-C6-haloalkenyl" refers to an alkyl group having 2 or 6 carbon atoms as defined above, where some or all of the hydrogen atoms in these groups can be replaced by halogen atoms as described above.

[0049] The term "C2-C6-alkynyl" refers to a straight-chain or branched-chain 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.

[0050] The term "C2-C6-haloalkynyl" refers to an alkyl group having 2 or 6 carbon atoms as defined above, wherein some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as described above.

[0051] 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. Thus, saturated three-, four-, five-, six-, seven-, eight-, nine- or ten-membered carbocyclic groups or carbocycles are "C3-C 10 -cycloalkyl".

[0052] The term "C3-C8-cycloalkyl-C1-C4-alkyl" refers to an alkyl group having 1 to 4 carbon atoms (as defined above), wherein at least one hydrogen atom of the alkyl group is replaced by a cycloalkyl group having 3 to 8 carbon atoms (as defined above).

[0053] The term "saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine- or ten-membered heterocyclic group or heterocycle, wherein the heterocyclic group or heterocycle contains 1, 2, 3 or 4 heteroatoms selected from N, O and S" is to be understood to mean both saturated heterocycles and partially unsaturated heterocycles, wherein the ring member atoms of the heterocycle include, in addition to carbon atoms, 1, 2, 3 or 4 heteroatoms independently selected from the group consisting of O, N and S. For example:

[0054] 3- or 4-membered saturated heterocycles containing 1 or 2 heteroatoms selected from the group consisting of O, N and S as ring members, such as ethylene oxide, aziridine, thiirane, oxetane, azetidine, thietane, [1,2]dioxetane, [1,2]dithietane, [1,2]diazetane; and

[0055] A 5- or 6-membered saturated or partially unsaturated heterocycle containing 1, 2 or 3 heteroatoms selected 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, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl, 1,3,4-triazol-2-yl, 2,3-dihydrofuran-2-yl, 2,3-dihydrofuran-3-yl, 2,4-dihydrofuran-2-yl, 2,4-dihydrofuran-3-yl, 2,3-dihydrothiophen-2-yl, 2,3-dihydrothiophen-3-yl, 2,4-dihydrothiophen-2-yl, 2,4-dihydrothiophen-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-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2-isothiazolin-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-hexahydro-1,3,5-triazin-2-yl and 1,2,4-hexahydro-1,2,4-triazin-3-yl, and also the corresponding -ylidene groups; and,

[0056] 7-membered saturated or partially unsaturated heterocycles such as tetra- and hexahydroazepinyl, such as 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- -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 such as 2,3,4,5-tetrahydro[1H]oxepin- -2-, -3-, -4-, -5-, -6- or -7-yl, 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, hexahydrooxepin- -1-, -2-, -3- or -4-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.

[0057] The term "substituted" means substituted by 1, 2, 3 or up to the maximum possible number of substituents.

[0058] The term "5- or 6-membered heteroaryl" or "5- or 6-membered heteroaromatic group" refers to an aromatic ring system containing 1, 2, 3 or 4 heteroatoms independently selected from the group consisting of N, O and S in addition to carbon atoms, for example

[0059] 5-membered heteroaryl, such as pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thiophen-2-yl, thiophen-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-triazol-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; or

[0060] 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.

[0061] Hereinafter, specific embodiments of the compounds of the present invention are described. Among them, the specific meanings of the corresponding substituents are further detailed, and these meanings are in each case by themselves and in any combination with each other are specific embodiments of the present invention.

[0062] In addition, with respect to the variables, generally, the embodiments of Compound I are equally applicable to the intermediates.

[0063] According to one embodiment of the compound having Formula I, R 1 is independently selected from H, halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl in each case, preferably R 1 is independently selected from H, C1-C4-alkyl, C1-C4-haloalkyl in each case, more preferably R 1 is independently selected from H, C1-C4-alkyl in each case, most preferably R 1 is H in each case.

[0064] According to one embodiment of the compound having Formula I, R 2Selected from halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, O-C1-C6-alkyl, O-C2-C6-alkenyl, O-C2-C6-alkynyl, C3-C6-cycloalkyl, S-C1-C6-alkyl, S-C2-C6-alkenyl, S-C2-C6-alkynyl.

[0065] According to one embodiment of the compound of formula I, R 2 Is independently selected in each case from C1-C4-alkyl and C1-C4-haloalkyl, preferably R 2 Is independently selected in each case from H, C1-C4-alkyl, C1-C4-haloalkyl, more preferably R 2 Is independently selected in each case from CH3 and CF2H, most preferably R 2 Is CH3 in each case.

[0066] According to yet another embodiment of formula I, R 2 Is halogen, especially F, Cl, Br or I, more specifically F, Cl or Br, especially F or Cl.

[0067] According to yet another embodiment of formula I, R 2 Is F.

[0068] According to yet another embodiment of formula I, R 2 Is Cl.

[0069] According to yet another embodiment of formula I, R 2 Is Br.

[0070] According to yet another embodiment of formula I, R 2 Is CN.

[0071] According to yet another embodiment of formula I, R 2 Is C1-C6-alkyl, especially C1-C4-alkyl, such as CH3 or C2H5, especially CH3 or CH2CH3.

[0072] According to yet another embodiment of formula I, R 2 Is C1-C6-haloalkyl, especially C1-C4-haloalkyl, such as CF3.

[0073] According to yet another embodiment of formula I, R 2 Is C2-C6-alkenyl, especially C2-C4-alkenyl, such as CH=CH2, C(CH3)=CH2, CH2CH=CH2.

[0074] According to another specific embodiment of formula I, R2 is a C2-C6-haloalkenyl, especially a C2-C4-haloalkenyl, more specifically a C2-C3-haloalkenyl, 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.

[0075] According to another embodiment of formula I, R 2 is a C2-C6-alkynyl or a C2-C6-haloalkynyl, especially a C2-C4-alkynyl or a C2-C4-haloalkynyl, such as CΞCH, CH2CΞCH, CΞCCl, CH2CΞCCl, or CCl2CΞCCl.

[0076] According to another specific embodiment of formula I, R 2 is an O-C1-C6-alkyl, especially a C1-C4-alkyl, more specifically a C1-C2-alkoxy. R 2 is such as OCH3 or OCH2CH3.

[0077] According to another specific embodiment of formula I, R 2 is an O-C1-C6-alkyl.

[0078] According to another specific embodiment of formula I, R 2 is an O-C2-C6-alkenyl, especially a C2-C4-alkenyl, more specifically a C2-C3-alkenyl. R 2 is such as OCH=CH2, OCH2CH=CH2.

[0079] According to another specific embodiment of formula I, R 2 is an O-C2-C6-alkynyl, especially a C2-C6-alkynyl, especially a C2-C4-alkynyl, more specifically a C2-C3-alkynyl. R 2 is such as O-CH2-CΞCH.

[0080] According to another embodiment of formula I, R 2 is a C3-C6-cycloalkyl, especially cyclopropyl or cyclobutyl.

[0081] According to another specific embodiment of formula I, R 2 is an S-C1-C6-alkyl, especially a C1-C4-alkyl, more specifically a C1-C2-alkoxy. R 2 is such as SCH3 or SCH2CH3.

[0082] According to another specific embodiment of formula I, R 2is an S-C1-C6-alkyl group.

[0083] In another specific embodiment according to formula I, R 2 is an S-C2-C6-alkenyl group, especially a C2-C4-alkenyl group, more specifically a C2-C3-alkenyl group. R 2 is such as SCH=CH2, SCH2CH=CH2.

[0084] In another specific embodiment according to formula I, R 2 is an S-C2-C6-alkynyl group, especially a C2-C6-alkynyl group, especially a C2-C4-alkynyl group, more specifically a C2-C3-alkynyl group. R 2 is such as S-CH2-CΞCH.

[0085] A particularly preferred embodiment of R according to the present invention 2 is shown in Table P2 below, where each row from P2-1 to P2-21 corresponds to a specific embodiment of the present invention, and any combination of P2-1 to P2-21 with each other is a preferred embodiment of the present invention. The point of attachment of the carbon atom bonded to R 2 is marked with "#" in the figure.

[0086] Table P2:

[0087]

[0088]

[0089] In one embodiment according to formula I, R 3 is selected from the group consisting of: C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, especially CH3, C2H5, CF3, CH2F, CHF2, cyclopropyl, cyclobutyl, more specifically CH3, CH2F, CF2H, CF3, cyclopropyl, cyclobutyl, and most preferably CH3, CF2H.

[0090] In yet another embodiment according to formula I, R 3 is a C1-C6-alkyl group, especially a C1-C4-alkyl group, such as CH3 or C2H5, especially CH3 or CH2CH3.

[0091] In yet another embodiment according to formula I, R 3 is a C1-C6-haloalkyl group, especially a C1-C4-haloalkyl group, such as CF3, FCH2, F2CH, CF3CH2.

[0092] In yet another embodiment according to formula I, R 3is a C2-C6-alkenyl, especially a C2-C4-alkenyl, such as CH=CH2, C(CH3)=CH2, CH2CH=CH2.

[0093] In yet another embodiment according to formula I, R3 is a C2-C6-alkynyl or a C2-C6-haloalkynyl, especially a C2-C4-alkynyl or a C2-C4-haloalkynyl, such as C≡CH, CH2C≡CH, C≡CCl, CH2C≡CCl, or CCl2C≡CCl.

[0094] In another specific embodiment according to formula I, R 3 is O-C1-C6-alkyl, especially C1-C4-alkyl, more specifically C1-C2-alkoxy. R 3 is, for example, OCH3 or OCH2CH3.

[0095] In another specific embodiment according to formula I, R 3 is O-C2-C6-alkenyl, especially C2-C4-alkenyl, more specifically C2-C3-alkenyl. R 3 is, for example, OCH=CH2, OCH2CH=CH2.

[0096] In another specific embodiment according to formula I, R 3 is O-C2-C6-alkynyl, especially C2-C6-alkynyl, especially C2-C4-alkynyl, more specifically C2-C3-alkynyl. R 3 is, for example, O-CH2-C≡CH.

[0097] In another specific embodiment according to formula I, R 3 is O-C1-C6-haloalkyl, especially OCF3, OCCl3, OFCH2, OClCH2, OF2CH, OCl2CH, OCF3CH2, OCCl3CH2 or OCF2CHF2, more specifically OCF3, OF2CH, OFCH2.

[0098] In yet another embodiment according to formula I, R 3 is C3-C6-cycloalkyl, especially cyclopropyl, cyclobutyl.

[0099] In another specific embodiment according to formula I, R 3 is S-C1-C6-alkyl, especially C1-C4-alkyl, more specifically C1-C2-alkoxy. R 2 is, for example, SCH3 or SCH2CH3.

[0100] In another specific embodiment according to formula I, R 3 is S-C1-C6-alkyl.

[0101] According to another specific embodiment of formula I, R 3 is S-C2-C6-alkenyl, especially C2-C4-alkenyl, more specifically C2-C3-alkenyl. R 2 is such as SCH=CH2, SCH2CH=CH2.

[0102] According to another specific embodiment of formula I, R 3 is S-C2-C6-alkynyl, especially C2-C6-alkynyl, especially C2-C4-alkynyl, more specifically C2-C3-alkynyl. R 2 is such as S-CH2-CΞCH.

[0103] A particularly preferred embodiment of R 3 according to the present invention is shown in Table P3 below, where each row from P3-1 to P3-17 corresponds to a specific embodiment of the present invention, and any combination of P3-1 to P3-17 with each other is a preferred embodiment of the present invention. The point of attachment of the carbon atom bonded to R 3 is marked with "#" in the figure.

[0104] Table P3:

[0105]

[0106] According to one embodiment of the compound having formula I, R 4 is independently selected from H, halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl in each case, and preferably R 4 is independently selected from H, C1-C4-alkyl, C1-C4-haloalkyl in each case, and more preferably R 4 is independently selected from H, C1-C4-alkyl in each case, and most preferably R 4 is H in each case.

[0107] According to one embodiment of the compound having formula I, R 5 is independently selected from hydrogen, halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, benzyl, five- or six-membered heteroaryl or five- or six-membered CH2-heteroaryl in each case; wherein the heteroaryl contains one, two or three heteroatoms selected from N, O and S; and wherein these aliphatic or aromatic groups are unsubstituted or carry 1, 2 or 3 substituents R 5a ; wherein each R 5a is independently halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl or O-C1-C6-alkyl.

[0108] According to one embodiment of the compound of formula I, R 5 is independently selected in each case from C1-C6-alkyl (Example 5.1), C1-C6-haloalkyl (Example 5.2), C1-C6-alkyl-O-C1-C6-alkyl (Example 5.3), phenyl, CH2-phenyl (Example 5.4), where phenyl and CH2-phenyl are unsubstituted or substituted by one or two halogens.

[0109] According to a further embodiment of the compound of formula I, R 5 is CH3 or CF3.

[0110] According to a further embodiment of the compound of formula I, R 5 is CH3.

[0111] According to a further embodiment of the compound of formula I, R 5 is CH2CH3, CH(CH3)2, CH(CH3)CH2CH3, C(CH3)3, CH2-CH(CH3)2, CH2-C(CH3)3, CH2-O-CH3.

[0112] According to a further embodiment of the compound of formula I, R 5 is CH=CH2, CH2CH=CH2.

[0113] According to a further embodiment of the compound of formula I, R 5 is 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.

[0114] According to one embodiment of the compound of formula I, R 6 is independently selected in each case from hydrogen, halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, benzyl, a five- or six-membered heteroaryl or a five- or six-membered CH2 heteroaryl; where the heteroaryl contains one, two or three heteroatoms selected from N, O and S; and where these aliphatic or aromatic groups are unsubstituted or carry 1, 2 or 3 substituents R 6a ; where each R 6a is independently halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl or O-C1-C6-alkyl.

[0115] According to one embodiment of the compound of formula I, R 6Independently selected from C1-C6-alkyl (Example 6.1), C1-C6-alkyl-O-phenyl (Example 6.2), C1-C6-alkyl-O-C1-C6-alkyl (Example 6.3) in each case.

[0116] According to a further embodiment of the compound of formula I, R 6 is 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, CH=CH2, CH2CH=CH2, CH2-phenyl.

[0117] According to a further embodiment of the compound of formula I, R 5 and R 6 together with the C atom to which they are bonded form a C3-C6-cycloalkyl, or a 3- to 6-membered saturated heterocycle containing 1, 2 or 3 heteroatoms from the group consisting of O and S, wherein the cycloalkyl or heterocycle may be unsubstituted or substituted by halogen, C1-C6-alkyl, C1-C6-haloalkyl.

[0118] According to a further embodiment of the compound of formula I, R 5 and R 6 form a C3-C6-cycloalkyl (Example 6.4).

[0119] According to a further embodiment of the compound of formula I, R 5 and R 6 form a 3- to 6-membered saturated heterocycle containing 1, 2 or 3 heteroatoms from the group consisting of O and S.

[0120] According to a further embodiment of the compound of formula I, R 5 and R 6 together form a (=O) group (Example 6.5).

[0121] According to a further embodiment of the compound of formula I, R 5 and R 6 together form a (=S) group.

[0122] The preferred embodiments of R 5 and R 6 in the present invention are shown in Table P5 below, where each row from P5-1 to P5-19 corresponds to a specific embodiment of the present invention, and any combination of P5-1 to P5-19 with each other is a preferred embodiment of the present invention. With R5 and R 6 The attachment points of the carbon atoms bonded to R are marked with "#" in the figure.

[0123] Table P5,6:

[0124]

[0125]

[0126] According to one embodiment of the compound having formula I, R 7 is independently selected, in each case, from hydrogen, halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, benzyl, a five- or six-membered heteroaryl or a five- or six-membered CH2-heteroaryl; where the heteroaryl contains one, two or three heteroatoms selected from N, O and S; and where these aliphatic or aromatic groups are unsubstituted or carry 1, 2 or 3 substituents R 7a ; where each R 7a is independently halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl or O-C1-C6-alkyl.

[0127] According to one embodiment of the compound having formula I, R 7 is independently selected, in each case, from C1-C6-alkyl (Example 7.1), C1-C6-haloalkyl (Example 7.2), C1-C6-alkyl-O-C1-C6-alkyl (Example 7.3), phenyl, CH2-phenyl (Example 7.4), where phenyl and CH2-phenyl are unsubstituted or substituted by one or two halogens.

[0128] According to a further embodiment of the compound having formula I, R 7 is CH3 or CF3.

[0129] According to a further embodiment of the compound having formula I, R 7 is CH3.

[0130] According to a further embodiment of the compound having formula I, R 7 is CH2CH3, CH(CH3)2, CH(CH3)CH2CH3, C(CH3)3, CH2-CH(CH3)2, CH2-C(CH3)3, CH2-O-CH3, CH=CH2, CH2CH=CH2.

[0131] According to a further embodiment of the compound having formula I, R 7is 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.

[0132] According to one embodiment of the compound of formula I, R 8 is independently selected, in each case, from hydrogen, halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, benzyl, a five- or six-membered heteroaryl or a five- or six-membered CH2-heteroaryl; where the heteroaryl contains one, two or three heteroatoms selected from N, O and S; and where these aliphatic or aromatic groups are unsubstituted or carry 1, 2 or 3 substituents R 8a ; where each R 8a is independently halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl or O-C1-C6-alkyl.

[0133] According to one embodiment of the compound of formula I, R 8 is independently selected, in each case, from C1-C6-alkyl (Example 8.1), C1-C6-alkyl-O-phenyl (Example 8.2), C1-C6-alkyl-O-C1-C6-alkyl (Example 8.3).

[0134] According to a further embodiment of the compound of formula I, R 8 is 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, CH=CH2, CH2CH=CH2, CH2-phenyl.

[0135] According to a further embodiment of the compound of formula I, R 7 and R 8 together with the C atom to which they are bonded form a C3-C6-cycloalkyl, or a 3- to 6-membered saturated heterocycle containing 1, 2 or 3 heteroatoms from the group consisting of O and S, where the cycloalkyl or heterocycle may be unsubstituted or substituted by halogen, C1-C6-alkyl, C1-C6-haloalkyl.

[0136] According to a further embodiment of the compound of formula I, R 7 and R 8 form a C3-C6-cycloalkyl (Example 8.4).

[0137] According to a further embodiment of the compound of formula I, R 7 and R 8 form a 3- to 6-membered saturated heterocycle containing 1, 2 or 3 heteroatoms selected from the group consisting of O and S.

[0138] According to a further embodiment of the compound of formula I, R 7 and R 8 together form a (=O) group (Example 8.5).

[0139] Preferred embodiments of R 7 , R 8 of the present invention are in Table P78 below, where each row from P7-1 to P7-19 corresponds to a specific embodiment of the present invention, and where P7-1 to P7-19 can also be arbitrarily combined with each other as preferred embodiments of the present invention. The point of attachment of the carbon atom bonded to R 7 and R 8 is marked with "#" in the figure.

[0140] Table P7,8:

[0141]

[0142]

[0143] According to a further embodiment of the compound of formula I,

[0144] R 9 is independently selected in each case from H, 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)-N(H)C1-C4-alkyl, -C(=O)-N(C1-C4-alkyl)2, C1-C6-alkyl, C1-C6-alkoxy, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, -S(=O)2-R 9a, a five- or six-membered heteroaryl, aryl or benzyl; wherein the heteroaryl contains 1, 2 or 3 heteroatoms selected from N, O and S as ring members; wherein the benzene ring in the aryl and benzyl is unsubstituted or bears 1, 2, 3, 4 or 5 substituents selected from the group consisting of: CN, halogen, OH, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy; wherein the benzene ring in the benzyl is unsubstituted or bears 1, 2 or 3 substituents selected from the group consisting of: CN and halogen;

[0145] wherein

[0146] R 9a is C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl or benzyl, wherein the benzene ring in the last two mentioned groups is unsubstituted or bears 1, 2 or 3 substituents each independently selected from the group consisting of: halogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl and C2-C6-haloalkynyl.

[0147] In yet another embodiment according to formula I, R 9 is Cl, F.

[0148] In yet another embodiment according to formula I, R 9 is CN, CH2CN or CH(CH3)CN.

[0149] In another specific embodiment according to formula I, R 9 is CH(=O).

[0150] In another specific embodiment according to formula I, R 9 is OCH3 or OCH2CH3.

[0151] In another specific embodiment according to formula I, R 9 is C(=O)C1-C6-alkyl, wherein the alkyl is CH3, C2H5, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl or isopentyl.

[0152] In another specific embodiment according to formula I, R 9 is C(=O)C2-C6-alkenyl, wherein the alkenyl is CH=CH2, CH2CH=CH2.

[0153] In another specific embodiment according to formula I, R 9 is C(=O)C2-C6-alkynyl, wherein the alkynyl is C≡CH, CH2C≡CH.

[0154] In another specific embodiment according to formula I, R 9 is C(=O)C3-C6-cycloalkyl, where the cycloalkyl is cyclopropyl (C3H7) or cyclobutyl (C4H9).

[0155] In another specific embodiment according to formula I, R 9 is C(=O)NH-C1-C4-alkyl or C(=O)N-(C1-C4-alkyl)2, where the alkyl is CH3, C2H5, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl.

[0156] In yet another embodiment according to formula I, R 9 is C1-C6-alkyl, such as CH3, C2H5, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl or isopentyl.

[0157] In yet another embodiment according to formula I, R 9 is C1-C6-alkyl, especially C1-C4-alkyl, such as CH3, C2H5, n-propyl, isopropyl.

[0158] In yet another embodiment according to formula I, R 9 is C1-C6-haloalkyl, especially C1-C4-haloalkyl, such as CF3, CCl3, FCH2, ClCH2, F2CH, Cl2CH, CF3CH2, CCl3CH2 or CF2CHF2.

[0159] In yet another embodiment according to formula I, R 9 is C3-C6-cycloalkyl, especially cyclopropyl.

[0160] In yet another embodiment according to formula I, R 9 is C3-C6-halocycloalkyl. In a specific embodiment, R 9b is fully or partially halogenated cyclopropyl, such as 1-F-cyclopropyl, 1-Cl-cyclopropyl, 1,1-F2-cyclopropyl, 1,1-Cl2-cyclopropyl.

[0161] In yet another embodiment according to formula I, R 9 is C2-C6-alkenyl, especially C2-C4-alkenyl, such as CH=CH2, C(CH3)=CH2, CH2CH=CH2.

[0162] In another specific embodiment according to formula I, R 9is a C2-C6-haloalkenyl, in particular a C2-C4-haloalkenyl, more particularly a C2-C3-haloalkenyl, 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.

[0163] In yet another embodiment according to formula I, R 9 is a C2-C6-alkynyl or a C2-C6-haloalkynyl, in particular a C2-C4-alkynyl or a C2-C4-haloalkynyl, such as C≡CH, CH2C≡CH.

[0164] In yet another embodiment according to formula I, R 9 is -S(=O)2-R 9a , where R 9a is preferably a C1-C6-alkyl, in particular a C1-C4-alkyl, such as CH3, C2H5, n-propyl, isopropyl.

[0165] In yet another embodiment according to formula I, R 9 is an aryl, in particular a phenyl, where the aryl or phenyl moiety is in each case unsubstituted or substituted by the same or different groups R 9b independently of one another selected from: halogen, C1-C2-alkyl, C1-C2-alkoxy, C1-C2-haloalkyl and C1-C2-haloalkoxy, in particular F, Cl, Br, CH3, OCH3, CF3 and OCF3. According to one embodiment, R 9 is an unsubstituted phenyl. According to another embodiment, R 9 is a phenyl substituted by one, two or three (in particular one) halogen(s) especially selected from F, Cl and Br, more particularly selected from F and Cl.

[0166] In yet another embodiment according to formula I, R 9is a 5-membered heteroaryl such as pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thiophen-2-yl, thiophen-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-triazol-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.

[0167] According to yet another embodiment of formula I, R 9 is a 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.

[0168] According to yet another embodiment of formula I, R 9 is independently selected in each case from H, halogen, OH, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy and C3-C6-cycloalkyl, where the acyclic part of R 9 is unsubstituted or substituted by the same or different groups R as defined and preferably as defined herein 9a and where the carbocyclic, phenyl and heteroaryl parts of R 9 are unsubstituted or substituted by the same or different groups R as defined and preferably as defined herein 9b substituted.

[0169] Particularly preferred embodiments of R according to the invention 9 are in Table P9 below, where each row from P9-1 to P9-32 corresponds to a specific embodiment of the invention, where P9-1 to P9-32 can also be arbitrarily combined with each other to be preferred embodiments of the invention. The point of attachment of the carbon atom bonded to R 9 is marked with "#" in the figure.

[0170] Table P9:

[0171]

[0172] According to one embodiment of the compound of formula I, X is independently selected in each case from halogen (Embodiment X.1), CN, C1-C6-alkyl (Embodiment X.2), C1-C6-haloalkyl (Embodiment X.3), O-C1-C6-alkyl (Embodiment X.4), O-C1-C6-haloalkyl (Embodiment X.5).

[0173] According to one embodiment of the compound of formula I, X is independently selected in each case from halogen, O-C1-C6-alkyl.

[0174] According to one embodiment of the compound of formula I, X is independently selected in each case from F or Cl.

[0175] According to one embodiment of the compound of formula I, X is C3-C6-cycloalkyl.

[0176] According to one embodiment of the compound of formula I, n is 0.

[0177] According to one embodiment of the compound of formula I, n is 1.

[0178] According to one embodiment of the compound of formula I, n is 2.

[0179] According to one embodiment, Xn is defined as follows:

[0180]

[0181] and X is selected from F, Cl, I, CH3, cyclopropyl, CH=CH2, CΞCH, OCH3, OCHF2, CF3, CHF2, CH2CH3, CN.

[0182] According to one embodiment, Xn is defined as follows:

[0183]

[0184] and X is F.

[0185] According to one embodiment, Xn is defined as follows:

[0186]

[0187] and X is selected from F, Cl, I, CH3, cyclopropyl, CH=CH2, CΞCH, OCH3, OCHF2, CF3, CHF2, CH2CH3, CN.

[0188] According to one embodiment, Xn is defined as follows:

[0189]

[0190] And X is F.

[0191] According to one embodiment, n is 0.

[0192] In a further aspect, the present invention relates to embodiments E.1 to E.275 listed in Table E, which represent preferred combinations of the embodiments defined for each of the variables R 2 , R 3 and X (represented by embodiments X.1 to X.6), and n in the compounds of formula I is defined as follows.

[0193]

[0194] Table E:

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204] In a further aspect, the present invention relates to embodiments E.1 to E.275 listed in Table E, wherein R 5 is represented by embodiment 5.1, and R 6 is represented by embodiment 6.1.

[0205] In a further aspect, the present invention relates to embodiments E.1 to E.275 listed in Table E, wherein R 5 is represented by embodiment 5.2, and R 6 is represented by embodiment 6.1.

[0206] In a further aspect, the present invention relates to embodiments E.1 to E.275 listed in Table E, wherein R 5 is represented by embodiment 5.3, and R 6 is represented by embodiment 6.1.

[0207] In another aspect, the present invention relates to Examples E.1 to E.275 listed in Table E, where R 5 is represented by Example 5.4, and R 6 is represented by Example 6.1.

[0208] In another aspect, the present invention relates to Examples E.1 to E.275 listed in Table E, where R 5 is represented by Example 5.1, and R 6 is represented by Example 6.2.

[0209] In another aspect, the present invention relates to Examples E.1 to E.275 listed in Table E, where R 5 is represented by Example 5.2, and R 6 is represented by Example 6.2.

[0210] In another aspect, the present invention relates to Examples E.1 to E.275 listed in Table E, where R 5 is represented by Example 5.3, and R 6 is represented by Example 6.2.

[0211] In another aspect, the present invention relates to Examples E.1 to E.275 listed in Table E, where R 5 is represented by Example 5.4, and R 6 is represented by Example 6.2.

[0212] In another aspect, the present invention relates to Examples E.1 to E.275 listed in Table E, where R 5 is represented by Example 5.1, and R 6 is represented by Example 6.3.

[0213] In another aspect, the present invention relates to Examples E.1 to E.275 listed in Table E, where R 5 is represented by Example 5.2, and R 6 is represented by Example 6.3.

[0214] In another aspect, the present invention relates to Examples E.1 to E.275 listed in Table E, where R 5 is represented by Example 5.3, and R 6 is represented by Example 6.3.

[0215] In another aspect, the present invention relates to Examples E.1 to E.275 listed in Table E, where R 5 is represented by Example 5.4, and R 6 is represented by Example 6.3.

[0216] In another aspect, the present invention relates to Examples E.1 to E.275 listed in Table E, where R 5 and R 6 are represented by Example 6.4.

[0217] In another aspect, the present invention relates to Examples E.1 to E.275 listed in Table E, where R 5 and R 6 are represented by Example 6.5.

[0218] In another aspect, the present invention relates to Examples E.1 to E.275 listed in Table E, where R 7 is represented by Example 7.1, and R 8 is represented by Example 8.1.

[0219] In another aspect, the present invention relates to Examples E.1 to E.275 listed in Table E, where R 7 is represented by Example 7.2, and R 8 is represented by Example 8.1.

[0220] In another aspect, the present invention relates to Examples E.1 to E.275 listed in Table E, where R 7 is represented by Example 7.3, and R 8 is represented by Example 8.1.

[0221] In another aspect, the present invention relates to Examples E.1 to E.275 listed in Table E, where R 7 is represented by Example 7.4, and R 8 is represented by Example 8.1.

[0222] In another aspect, the present invention relates to Examples E.1 to E.275 listed in Table E, where R 7 is represented by Example 7.1, and R 8 is represented by Example 8.2.

[0223] In another aspect, the present invention relates to Examples E.1 to E.275 listed in Table E, where R 7 is represented by Example 7.2, and R 8 is represented by Example 8.2.

[0224] In another aspect, the present invention relates to Examples E.1 to E.275 listed in Table E, where R 7 is represented by Example 7.3, and R 8 is represented by Example 8.2.

[0225] In another aspect, the present invention relates to Examples E.1 to E.275 listed in Table E, where R7 as represented by Example 7.4, and R 8 is represented by Example 8.2.

[0226] In a further aspect, the present invention relates to Examples E.1 to E.275 listed in Table E, wherein R 7 is represented by Example 7.1, and R 8 is represented by Example 8.3.

[0227] In a further aspect, the present invention relates to Examples E.1 to E.275 listed in Table E, wherein R 7 is represented by Example 7.2, and R 8 is represented by Example 8.3.

[0228] In a further aspect, the present invention relates to Examples E.1 to E.275 listed in Table E, wherein R 7 is represented by Example 7.3, and R 8 is represented by Example 8.3.

[0229] In a further aspect, the present invention relates to Examples E.1 to E.275 listed in Table E, wherein R 7 is represented by Example 7.4, and R 8 is represented by Example 8.3.

[0230] In a further aspect, the present invention relates to Examples E.1 to E.275 listed in Table E, wherein R 7 and R 8 are represented by Example 8.4.

[0231] In a further aspect, the present invention relates to Examples E.1 to E.275 listed in Table E, wherein R 7 and R 8 are represented by Example 8.7.

[0232] In particular, considering their uses, according to one embodiment, it is preferred that the compounds are those of Compounds I.A-1, I.A-2, I.A-3, I.A-4; which are compiled in Tables 1a to 13a. In addition, each group mentioned for the substituents in the tables by itself (independently of the combinations mentioned) is a particularly preferred aspect of the substituents.

[0233]

[0234] Table 1a Compounds of formulae I.A-1, I.A-2, I.A-3, I.A-4, wherein R 9 is CH3, and the X of each individual compound 1 , X 2 , R 5 , R6 , R 7 and R 8 In each case, the meaning of the combination of and R corresponds to a row in Table B (Compounds I.A-1.1a.B-1 to I.A-1.1a.B-672, I.A-2.1a.B-1 to I.A-2.1a.B-672, I.A-3.1a.B-1 to I.A-3.1a.B-672, I.A-4.1a.B-1 to I.A-4.1a.B-672).

[0235] Table 2a Compounds of formulae I.A-1, I.A-2, I.A-3, I.A-4, where R 9 is CH2CH3, and for each individual compound, X 1 , X 2 , R 5 , R 6 , R 7 and R 8 In each case, the meaning of the combination of and R corresponds to a row in Table B (Compounds I.A-1.2a.B-1 to I.A-1.2a.B-672, I.A-2.2a.B-1 to I.A-2.2a.B-672, I.A-3.2a.B-1 to I.A-3.2a.B-672, I.A-4.2a.B-1 to I.A-4.2a.B-672).

[0236] Table 3a Compounds of formulae I.A-1, I.A-2, I.A-3, I.A-4, where R 9 is CH2CH2CH3, and for each individual compound, X 1 , X 2 , R 5 , R 6 , R 7 and R 8 In each case, the meaning of the combination of and R corresponds to a row in Table B (Compounds I.A-1.3a.B-1 to I.A-1.3a.B-672, I.A-2.3a.B-1 to I.A-2.3a.B-672, I.A-3.3a.B-1 to I.A-3.3a.B-672, I.A-4.3a.B-1 to I.A-4.3a.B-672)

[0237] Table 4a Compounds of formulae I.A-1, I.A-2, I.A-3, I.A-4, where R 9 is CN, and for each individual compound, X 1 , X 2 , R 5 , R 6 , R 7 and R 8The meaning of the combination corresponds to a row in Table B in each case (compounds I.A-1.4a.B-1 to I.A-1.4a.B-672, I.A-2.4a.B-1 to I.A-2.4a.B-672, I.A-3.4a.B-1 to I.A-3.4a.B-672, I.A-4.4a.B-1 to I.A-4.4a.B-672).

[0238] Table 5a Compounds of formula I.A-1, I.A-2, I.A-3, I.A-4, wherein R 9 is CH2CN, and for each individual compound, the meaning of the combination of X 1 、X 2 、R 5 、R 6 、R 7 and R 8 corresponds to a row in Table B in each case (compounds I.A-1.5a.B-1 to I.A-1.5a.B-672, I.A-2.5a.B-1 to I.A-2.5a.B-672, I.A-3.5a.B-1 to I.A-3.5a.B-672, I.A-4.5a.B-1 to I.A-4.5a.B-672).

[0239] Table 6a Compounds of formula I.A-1, I.A-2, I.A-3, I.A-4, wherein R 9 is CHO, and for each individual compound, the meaning of the combination of X 1 、X 2 、R 5 、R 6 、R 7 and R 8 corresponds to a row in Table B in each case (compounds I.A-1.6a.B-1 to I.A-1.6a.B-672, I.A-2.6a.B-1 to I.A-2.6a.B-672, I.A-3.6a.B-1 to I.A-3.6a.B-672, I.A-4.6a.B-1 to I.A-4.6a.B-672).

[0240] Table 7a Compounds of formula I.A-1, I.A-2, I.A-3, I.A-4, wherein R 9 is C(CH3)3, and for each individual compound, the meaning of the combination of X 1 、X 2 、R 5 、R 6 、R 7 and R 8The meaning of the combination corresponds in each case to a row in Table B (compounds I.A-1.7a.B-1 to I.A-1.7a.B-672, I.A-2.7a.B-1 to I.A-2.7a.B-672, I.A-3.7a.B-1 to I.A-3.7a.B-672, I.A-4.7a.B-1 to I.A-4.7a.B-672)

[0241] Table 8a Compounds of formula I.A-1, I.A-2, I.A-3, I.A-4, where R 9 is COCH3, and for each individual compound, the meaning of the combination of X 1 、X 2 、R 5 、R 6 、R 7 and R 8 corresponds in each case to a row in Table B (compounds I.A-1.8a.B-1 to I.A-1.8a.B-672, I.A-2.8a.B-1 to I.A-2.8a.B-672, I.A-3.8a.B-1 to I.A-3.8a.B-672, I.A-4.8a.B-1 to I.A-4.8a.B-672)

[0242] Table 9a Compounds of formula I.A-1, I.A-2, I.A-3, I.A-4, where R 9 is CH2C(CH3)3, and for each individual compound, the meaning of the combination of X 1 、X 2 、R 5 、R 6 、R 7 and R 8 corresponds in each case to a row in Table B (compounds I.A-1.9a.B-1 to I.A-1.9a.B-672, I.A-2.9a.B-1 to I.A-2.9a.B-672, I.A-3.9a.B-1 to I.A-3.9a.B-672, I.A-4.9a.B-1 to I.A.4-9a.B-672)

[0243] Table 10a Compounds of formula I.A-1, I.A-2, I.A-3, I.A-4, where R 9 is CH2CH=CH2, and for each individual compound, the meaning of the combination of X 1 、X 2 、R 5 、R 6 、R 7 and R 8The meaning of the combination corresponds to a row in Table B in each case (compounds I.A-1.10a.B-1 to I.A-1.10a.B-672, I.A-2.10a.B-1 to I.A-2.10a.B-672, I.A-3.10a.B-1 to I.A-3.10a.B-672, I.A-4.10a.B-1 to I.A-4.10a.B-672)

[0244] Table 11a Compounds of formula I.A-1, I.A-2, I.A-3, I.A-4, where R 9 is CH2CCH, and for each individual compound, the meaning of the combination of X 1 、X 2 、R 5 、R 6 、R 7 and R 8 corresponds to a row in Table B in each case (compounds I.A-1.11a.B-1 to I.A-1.11a.B-672, I.A-2.11a.B-1 to I.A-2.11a.B-672, I.A-3.11a.B-1 to I.A-3.11a.B-672, I.A-4.11a.B-1 to I.A-4.11a.B-672)

[0245] Table 12a Compounds of formula I.A-1, I.A-2, I.A-3, I.A-4, where R 9 is CH2C6H5, and for each individual compound, the meaning of the combination of X 1 、X 2 、R 5 、R 6 、R 7 and R 8 corresponds to a row in Table B in each case (compounds I.A-1.12a.B-1 to I.A-1.12a.B-672, I.A-2.12a.B-1 to I.A-2.12a.B-672, I.A-3.12a.B-1 to I.A-3.12a.B-672, I.A-4.12a.B-1 to I.A-4.12a.B-672)

[0246] Table 13a Compounds of formula I.A-1, I.A-2, I.A-3, I.A-4, where R 9 is H, and for each individual compound, the meaning of the combination of X 1 、X 2 、R 5 、R 6 、R 7 and R 8The meaning of the combination corresponds to a row in Table B in each case (Compounds I.A-1.13a.B-1 to I.A-1.13a.B-672, I.A-2.13a.B-1 to I.A-2.13a.B-672, I.A-3.13a.B-1 to I.A-3.13a.B-672, I.A-4.13a.B-1 to I.A-4.13a.B-672)

[0247] Table B

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266] The compounds of the present invention can be made as shown in the following schemes, wherein, unless otherwise indicated, the definition of each variable is as defined above for compounds of formula I. Compounds of formula I can be prepared according to methods described in the prior art or analogously to these methods. The synthesis utilizes starting materials that are commercially available or can be prepared according to conventional procedures starting from readily available compounds.

[0267] For example, compound I can be obtained via a benzoxazepine represented by formula (2): The benzoxazepines are prepared by alkylation or acylation with a series of alkyl halides and acyl chlorides, which can be prepared by reacting the benzoxazepines with a series of organic or inorganic bases such as potassium N-ethyl-N,N-diisopropylethylamine or sodium hydride. The reaction is preferably carried out at 0°C to room temperature, and in some cases, the slow reaction is carried out at a temperature up to 100°C and using 1-5 equivalents of a base and 1-3 equivalents of an alkylating / acylating agent, as described in CN 113264945; WO 2017 / 60854A1; J.Med.Chem [Journal of Medicinal Chemistry] (2014), 57, 10424-10442; or US2011 / 196150 A1.

[0268] Alternatively, compound I can be obtained by a benzoxazepine represented by formula (2): The amines are prepared by reductive amination of the amines with a series of aldehydes or ketones, which can be achieved with a series of reducing agents such as sodium tri(acetoxy)borohydride or sodium tetrahydroborate. The reaction is preferably carried out at 0°C to room temperature and using 2-6 equivalents of the reducing agent, as described in Tetrahedron Lett. (2011), 52, 1800-1803; WO 2008 / 54288A1; J. Med. Chem (2015), 58, 5256-5273; or ACS Med. Chem. Lett. (2020), 11, 1228-1235.

[0269]

[0270] Compound 2 can be reduced to a benzoxazepine represented by formula (3) by using a series of reducing agents such as sodium tetrahydroborate, lithium borohydride or sodium cyanoborohydride. It is prepared by a class. This reaction is preferably carried out at 0 °C to room temperature and using 1 - 6 equivalents of a reducing agent, as described in Bioorg. Med. Chem. Lett. [Bioorganic and Medicinal Chemistry Letters] (2022), 21, 6414 - 6416; US2016 / 222028 A1; Chem. Comm. [Chemical Communications] (2011), 47, 7845 - 7847; or J. Med. Chem. [Journal of Medicinal Chemistry] (2015), 58, 5256 - 5273.

[0271]

[0272] Compound (3) can also be prepared by a palladium - catalyzed Suzuki coupling reaction between a boronic acid derivative represented by formula (4) and an imidoyl halide derivative represented by formula (5) using a palladium complex in an organic solvent. Preferably, this reaction is carried out at an elevated temperature, preferably between 60 °C and 160 °C, and 1 - 3 equivalents of the boronic acid derivative represented by formula 3 are used per 1 equivalent of the imidoyl halide derivative (6), as described in WO 2009119089 A1.

[0273]

[0274] The imidoyl compound represented by formula (5) can be prepared by a method in which a cyclic amide represented by formula (6) is reacted in the presence of a suitable halogenating agent such as triphenylphosphine and carbon tetrahalide, triphenylphosphine dichloride, phosgene, oxalyl chloride, or thionyl chloride, as described in US2011 / 0136782A1.

[0275]

[0276] The compound represented by formula (6) can be prepared by the following methods: by Schmidt reaction of the cyclic acetophenone derivative represented by formula (8), or by Beckmann rearrangement of the oxime represented by formula (7). Various variations of both reactions have been reported. The Schmidt reaction can be carried out, for example, by reacting a ketone with sodium azide and a strong acid such as concentrated hydrochloric acid, sulfuric acid, trifluoroacetic acid or methanesulfonic acid in the absence of a solvent or in a solvent such as acetonitrile, chloroform or dichloromethane. In the Beckmann rearrangement, the oxime of a carbonyl compound is reacted with polyphosphoric acid or its trimethylsilyl ester, or with a Lewis acid such as aluminum triiodide or iron(III)-impregnated montmorillonite or with thionyl chloride in the absence of a solvent or in the presence of a solvent such as acetonitrile. Alternatively, it can also be prepared by forming the mesylate or tosylate of the oxime, followed by treatment with a base such as aqueous sodium hydroxide or with a Lewis acid such as diethylaluminum chloride, as described in Heterocycles (1994), 38(2), 305-18; US2011 / 0136782 A1.

[0277]

[0278] Alternatively, the compound represented by formula (6) can be prepared in one pot by copper(II)-catalyzed Beckmann rearrangement of ketone (8) using hydroxylamine-O-sulfonic acid as the aminating agent under mild reaction conditions, as described in Synthesis 2019, 51(19), 3709-3714.

[0279] The oxime (7) can be prepared using known methods by reacting with hydroxylamine hydrochloride in a solvent such as ethanol, followed by addition of a base such as pyridine or sodium acetate or aqueous sodium hydroxide at a temperature up to the boiling point of the solvent as required, as described in Bioorganic & Medicinal Chemistry (2008), 16(11), 6124-6130; Heterocyclic Communications (1998), 4(6), 547-557.

[0280]

[0281] The cyclic acetophenone derivatives represented by formula (9) are commercially available or can be obtained starting from 2-hydroxyacetophenone via a classical ring closing reaction using the corresponding ketone in the presence of pyrrolidine as described in Bioorganic & Medicinal Chemistry (2008), 16(11), 6124 - 6130; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1995).

[0282] Compound I and its compositions are each suitable as fungicides, being effective against a broad spectrum of phytopathogenic fungi, including soil-borne fungi, especially fungi from the classes Chytridiomycetes, Peronosporomycetes (synonym Oomycetes), Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, and Deuteromycetes (synonym Fungi imperfecti). They can be used in crop protection as foliar fungicides, seed dressing fungicides, and soil fungicides.

[0283] Compound I and its compositions are preferably useful for controlling phytopathogenic fungi on various cultivated plants such as cereals, e.g. wheat, rye, barley, triticale, oats or rice; sugar beet, such as sugar beet or fodder beet; fruits, e.g. pomes (apples, pears, etc.), stone fruits (e.g. plums, peaches, almonds, cherries) or soft fruits, also known as berries (strawberries, raspberries, blackberries, currants, etc.); leguminous plants, such as lentils, peas, alfalfa or soybeans; oil plants, such as rape, mustard, olive, sunflower, coconut, cocoa bean, castor oil plant, oil palm, groundnut or soybean; cucurbits, e.g. pumpkins, cucumbers or melons; fiber plants, such as cotton, flax, hemp, or jute; citrus fruits, such as oranges, lemons, grapefruits or tangerines; vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, gourds or red peppers; Lauraceae plants, such as avocado, cinnamon or camphor; energy and raw material plants, such as maize, soybean, rape, sugar cane or oil palm; maize; tobacco; nuts; coffee; tea; bananas; grapevines (table grapes and grape juice grapevines); hops; turf; stevia (also known as Stevia rebaudiana); natural rubber plants; or ornamental and forest plants, such as flowers, shrubs, broad-leaved trees or evergreen trees (conifers, eucalyptus, etc.); plant propagation material such as seeds; and crop material of these plants.

[0284] More preferably, compound I and its compositions are used, respectively, for controlling fungi on the following: field crops such as potato, sugar beet, tobacco, wheat, rye, barley, oats, rice, maize, cotton, soybean, rape, legumes, sunflower, coffee or sugar cane; fruits; vines; ornamental plants; or vegetables such as cucumber, tomato, kidney bean or pumpkin.

[0285] The term "plant propagation material" is to be understood as meaning all generative parts of plants, such as seeds; and vegetative plant material which can be used for plant propagation, such as cuttings and tubers (such as potatoes). This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, buds and other parts of plants; including seedlings and young plants which are transplanted after germination or after emergence from the soil.

[0286] Preferably, plant propagation materials are treated, respectively, with compound I and its compositions for controlling fungi on the following: cereals such as wheat, rye, barley and oats; rice, maize, cotton and soybean.

[0287] According to the invention, all the above cultivated plants are to be understood as including all species, subspecies, varieties, cultivars and / or hybrids belonging to the respective cultivated plants, including but not limited to winter and spring varieties, especially cereals such as wheat and barley, and rape, for example winter wheat, spring wheat, winter barley, etc.

[0288] Maize is also known as Indian corn or corn (maize / Zea mays), which includes all kinds of maize such as feed maize and sweet corn. According to the invention, all Zea mays or maize subspecies and / or varieties are included, especially floury maize (Zea mays var. amylacea), pop corn (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 maize variety), pod corn or wild corn (Zea mays var. tunicata) and striped corn (Zea mays var. japonica).

[0289] Most soybean cultivars can be classified as indeterminate and determinate growth habits, while wild soybean (Glycine soja) (the wild ancestor of soybean) is indeterminate (PNAS 2010, 107(19) 8563 - 856). Indeterminate growth habit (maturity groups, MG 00 to MG 4.9) is characterized by the continuation of vegetative growth after the onset of flowering, while determinate soybean cultivars (MG 5 to MG 8) characteristically have completed most of their vegetative growth at the onset of flowering. The present invention encompasses all soybean cultivars or varieties, particularly indeterminate and determinate cultivars or varieties.

[0290] The term "cultivated plant" is to be understood as including plants that have been modified by mutagenesis or genetic engineering in order to provide the plant with new traits or to modify existing traits. Mutagenesis includes random mutagenesis using X - rays or mutagenic chemicals, and also includes 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 typically uses recombinant DNA technology to generate modifications in the plant genome that cannot be readily obtained in nature by crossing, mutagenesis or natural recombination. Typically, one or more genes are integrated into the plant genome in order to add traits or improve or modify traits. These integrated genes are also referred to as transgenes, and plants containing such transgenes are referred to as transgenic plants. The plant transformation process typically results in a number of transformation events that differ in the genomic loci where the transgene has been integrated. A plant containing a specific transgene at a specific genomic locus is typically described as containing a specific "event", which is designated by a specific event name. Traits that have been introduced into plants or that have been modified include herbicide tolerance, insect resistance, increased yield, and tolerance to abiotic conditions such as drought.

[0291] Herbicide tolerance has been generated 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 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) has been generated by using transgenes.

[0292] Transgenes conferring herbicide tolerance traits include: for glyphosate tolerance: cp4epsps, epspsgrg23ace5, mepsps, 2mepsps, gat4601, gat4621, goxv247; for glufosinate tolerance: pat and bar; for 2,4-D tolerance: aad-1, aad-12; for dicamba tolerance: dmo; for benzonitrile herbicide tolerance: bxn; for sulfonylurea herbicide tolerance: zm-hra, csr1-2, gm-hra, S4-HrA; for ALS inhibitor tolerance: csr1-2; and for HPPD inhibitor tolerance: hppdPF, W336, avhppd-03.

[0293] Transgenic maize 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, 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 GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21, A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS-81419-2, GU262, W62, W98, FG72, and CV127. Transgenic cotton events containing a herbicide tolerance gene 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 a herbicide tolerance gene are, for example, but not exclusive of others, MON88302, HCR-1, HCN10, HCN28, HCN92, MS1, MS8, PHY14, PHY23, PHY35, PHY36, RF1, RF2, and RF3.

[0294] Transgenic genes that confer insect resistance are preferably toxin genes of Bacillus species and their synthetic variants, such as cry1A, cry1Ab, cry1Ab-Ac, cry1Ac, cry1A.105, cry1F, cry1Fa2, cry2Ab2, cry2Ae, mcry3A, ecry3.1Ab, cry3Bb1, cry34Ab1, cry35Ab1, cry9C, vip3A(a), vip3Aa20. In addition, transgenic genes of plant origin can be used, such as genes encoding protease inhibitors, such as CpTI and pinII. Another approach uses transgenic genes such as dvsnf7 to produce double-stranded RNA in plants.

[0295] Transgenic maize events containing insecticidal protein genes or double-stranded RNAs 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 insecticidal protein genes include, but are not limited to, MON87701, MON87751, and DAS-81419. Transgenic cotton events containing insecticidal protein genes 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, MLS 9124, 281-24-236, 3006-210-23, GHB119, and SGK321.

[0296] Cultivated plants with increased yield have been produced by using transgenic athb17 (e.g., maize event MON87403) or bbx32 (e.g., soybean event MON87712).

[0297] Cultivated plants with improved oil content have been produced by using the following transgenes: gm-fad2-1, Pj.D6D, Nc.Fad3, fad2-1A, and fatb1-A (e.g., soybean events 260-05, MON87705, and MON87769).

[0298] Tolerance to abiotic conditions such as drought has been produced by using transgenic cspB (maize event MON87460) and Hahb-4 (soybean event )

[0299] Traits are generally combined by combining genes in transformation events or by combining different events during the breeding process to produce cultivated plants with stacked traits. Preferred combinations of traits are combinations of herbicide tolerance traits to different groups of herbicides, combinations of insect tolerance to different species of insects, particularly tolerance to Lepidoptera and Coleoptera insects, combinations of herbicide tolerance with one or several types of insect resistance, combinations of herbicide tolerance with increased yield, and combinations of herbicide tolerance and tolerance to abiotic conditions.

[0300] Plants containing single or stacked traits, as well as the genes and events providing such traits, are well known in the art. For example, detailed information regarding mutagenesis or integration of genes and corresponding events is available from the websites of the institutions "International Service for the Acquisition of Agri-biotech Applications (ISAAA)" (http: / / www.isaaa.org / gmapprovaldatabase) and "Center for Environmental Risk Assessment (CERA)" (http: / / cera-gmc.org / GMCropDatabase). Additional information regarding specific events and methods for detecting such events, for canola events MS1, MS8, RF3, GT73, MON88302, KK179, can be found in WO 01 / 031042, WO 01 / 041558, WO 01 / 041558, WO 02 / 036831, WO 11 / 153186, WO13 / 003558; for cotton events MON1445, MON15985, MON531 (MON15985), LLCotton25, MON88913, COT102, 281-24-236, 3006-210-23, COT67B, GHB614, T304-40, GHB119, MON88701, 81910, can be found in WO 02 / 034946, WO 02 / 100163, WO 02 / 100163, WO 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;For maize events GA21, MON810, DLL25, TC1507, MON863, MIR604, LY038, MON88017, 3272, 59122, NK603, MIR162, MON89034, 98140, 32138, MON87460, 5307, 4114, MON87427, DAS40278, MON87411, 33121, MON87403, MON87419, see WO 98 / 044140, US 02 / 102582, US 03 / 126634, WO 04 / 099447, WO 04 / 011601, WO 05 / 103301, WO 05 / 061720, WO 05 / 059103, WO 06 / 098952, WO 06 / 039376, US2007 / 292854, WO07 / 142840, WO 07 / 140256, WO 08 / 112019, WO 09 / 103049, WO 09 / 111263, WO 10 / 077816, WO11 / 084621, WO 11 / 062904, WO 11 / 022469, WO 13 / 169923, WO 14 / 116854, WO 15 / 053998, WO15 / 142571; for potato events E12, F10, J3, J55, V11, X17, Y9, see WO 14 / 178910, WO 14 / 178913, WO 14 / 178941, WO 14 / 179276, WO 16 / 183445, WO 17 / 062831, WO 17 / 062825; for rice events LLRICE06, LLRICE601, LLRICE62, see WO 00 / 026345, WO 00 / 026356, WO 00 / 026345;And for the soybean events H7-1, MON89788, A2704-12, A5547-127, DP305423, DP356043, MON87701, MON87769, CV127, MON87705, DAS68416-4, MON87708, MON87712, SYHT0H2, DAS81419, DAS81419 x DAS44406-6, MON87751, see WO 04 / 074492, WO 06 / 130436, WO06 / 108674, WO 06 / 108675, WO 08 / 054747, WO 08 / 002872, WO 09 / 064652, WO 09 / 102873, WO10 / 080829, WO 10 / 037016, WO 11 / 066384, WO 11 / 034704, WO 12 / 051199, WO 12 / 082548, WO13 / 016527, WO 13 / 016516, WO 14 / 201235.;

[0301] The separate use of Compound I and its compositions on cultivated plants can result in effects specific to cultivated plants containing a certain transgene or event. These effects may involve alterations in growth behavior or altered resistance to biotic or abiotic stress factors. Such effects may particularly include increased yield, increased resistance or tolerance to insect, nematode, fungal, bacterial, mycoplasma, viral or viroid pathogens, and early vigour, early maturity or delayed maturity, cold or heat tolerance, and altered amino acid or fatty acid profiles or contents.

[0302] Compound I and its compositions are particularly suitable for controlling the causative agents of the following plant diseases:

[0303] Species of Albugo (white rust) on ornamental plants, vegetables (e.g., Albugo candida), and sunflowers (e.g., Albugo tragopogonis); species of Alternaria (alternaria leaf spot) on vegetables (e.g., Alternaria dauci or Alternaria porri), oilseed rape (Alternaria brassicicola or Alternaria brassicae), sugar beet (Alternaria tenuis), fruits (e.g., Alternaria grandis), rice, soybeans, potatoes, and tomatoes (e.g., Alternaria solani, Alternaria grandis, or Alternaria alternata), tomatoes (e.g., Alternaria solani or Alternaria alternata), and wheat (e.g., Alternaria triticina); species of Aphanomyces on sugar beet and vegetables; species of Ascochyta on cereals and vegetables, such as Ascochyta tritici (anthracnose) on wheat and Ascochyta hordei on barley; Aureobasidium zeae (synonym Kapatiella zeae) on maize; species of Bipolaris and Drechslera (sexual form: species of Cochliobolus), such as southern leaf blight (Drechslera maydis) or northern leaf blight (Bipolaris zeicola) on maize, such as spot blotch (Bipolaris sorokiniana) on cereals and, for example, Bipolaris oryzae on rice and turfgrass; Blumeria graminis (formerly known as Erysiphe graminis) (powdery mildew) on cereals (e.g., wheat or barley); Botrytis cinerea (sexual form: Botryotinia fuckeliana: gray mold) on fruits and berries (e.g., strawberries), vegetables (e.g., lettuce, carrots, celery, and cabbage); Botrytis squamosa or Botrytis allii on the onion family, oilseed rape, ornamental plants (e.g., Botrytis elliptica), vines, forest plants, and wheat; Bremia lactucae (downy mildew) on lettuce; species of Ceratocystis (synonym Ophiostoma) (rot or wilt) on broad-leaved and evergreen trees, such as Ceratocystis ulmi on elm treesulmi)(Dutch elm disease); maize (e.g., gray leaf spot: Cercospora zeae-maydis), rice, sugar beet (e.g., Cercospora beticola), sugar cane, vegetables, coffee, soybean (e.g., Cercospora sojina or Cercospora kikuchii) and Cercospora species on rice (Cercospora leafspot); Cladobotryum (synonym Dactylium) species on mushrooms (e.g., Cladobotryum mycophilum).

[0304] (formerly known as Dactylium dendroides), teleomorph: Nectria albertinii, Nectria rosella (synonym Hypomyces rosellus); Cladosporium species on tomato (e.g., C. fulvum: leaf mold) and cereals, e.g., C. herbarum on wheat (black ear); Claviceps purpurea on cereals (ergot); Cochliobolus (anamorph: Helminthosporium of the genus Bipolaris) species on maize (C. carbonum), cereals (e.g., C. sativus, anamorph: B. sorokiniana) and rice (e.g., C. miyabeanus, anamorph: H. oryzae) (leaf spot); Colletotrichum (teleomorph: Glomerella) species on cotton (e.g., C. gossypii), maize (e.g., C. graminicola: anthracnose stalk rot), soft fruits, potato (e.g., C. coccodes: black dot), bean (e.g., C. lindemuthianum), soybean (e.g., C. truncatum or C. gloeosporioides), vegetables (e.g., C. lagenarium or C. capsici), fruits (e.g., C. acutatum), coffee (e.g., C. coffeanum or C. kahawae) and a variety of crops (C. gloeosporioides) (anthracnose); Corticium species, e.g., C. sasakii on rice (sheath blight); Corynespora cassiicola on soybean, cotton and ornamental plants (leaf spot); Cycloconium species, e.g., C. oleaginum on olive trees; fruit trees, vines (e.g., Cylindrocladiumliriodendri), sexual form: Neonectria liriodendri: Black Foot Disease) and Cylindrocarpon species on ornamental plants (such as fruit tree canker or young vine decline, sexual form: Nectria or Neonectria species); Dematophora necatrix on soybeans (sexual form: Rosellinia necatrix) (root and stem rot); Diaporthe species, such as D. phaseolorum on soybeans (damping-off); Drechslera (synonym Helminthosporium, sexual form: Pyrenophora) species on corn, cereals such as barley (e.g., D. teres, net blotch) and wheat (e.g., D. tritici-repentis: tan spot), rice, and turfgrass; Esca (dieback, apoplexy) on vines, caused by Formitiporia punctata (synonym Phellinus punctata), F. mediterranea, Phaeomoniella chlamydospora (previously known as Phaeoacremonium chlamydosporum), Phaeoacremonium aleophilum, and / or Botryosphaeria obtusa; Elsinoe species on pome fruits (E. pyri), soft fruits (E. veneta: anthracnose), and vines (E. ampelina: anthracnose); Entyloma oryzae on rice (leaf smut); Epicoccum species on wheat (black mold); Erysiphe betae on sugar beets, Erysiphe pisi on vegetables (such as peas), for example, Erysiphe cichoracearum on cucurbits (such as gourds), cabbage, rape (such as Erysiphe cruciferarum),species of Erysiphe (powdery mildew) on cruciferarum); Eutypa lata (Eutypa canker or dieback, anamorph: Cytosporina lata, synonym Libertella blepharis) on fruit trees, vines, and ornamental woods; species of Exserohilum (synonym Helminthosporium) on maize (e.g., Exserohilum turcicum); species of Fusarium (teleomorph: Gibberella) on various plants (wilt, root or stem rot), such as Fusarium graminearum or Fusarium culmorum (root rot, scab or head blight) on cereals (e.g., wheat or barley), Fusarium oxysporum on tomatoes, Fusarium solani (f.sp. glycines, new synonym Fusarium virguliforme) on soybeans, and F. tucumaniae and F. brasiliense (both causing sudden death syndrome), and Fusarium verticillioides on maize; Gaeumannomyces graminis (take-all) on cereals (e.g., wheat or barley) and maize; species of Gibberella on cereals (e.g., Gibberella zeae) and rice (e.g., Gibberella fujikuroi: Bakanae disease); Glomerella cingulata on vines, pome fruits, and other plants and Glomerella gossypii on cotton; Grainstaining complex on rice; Guignardia bidwellii (black rot) on vines; species of Gymnosporangium on Rosaceae plants and junipers, such as Gymnosporangium sabinae (rust) on pears; species of Helminthosporium (synonym Drechslera, teleomorph: Cochliobolus) on maize, cereals, potatoes, and rice; species of Hemileia, such as Hemileia vastatrix on coffeevastatrix) (coffee leaf rust); Isariopsis clavispora (synonym Cladosporium vitis) on vines; Macrophomina phaseolina (synonym Macrophomina phaseoli) (root and stem rot) on soybeans and cotton; Microdochium nivale (synonym Fusarium nivale) (pink snow mold) on cereals (e.g., wheat or barley); Microsphaera diffusa (powdery mildew) on soybeans; Monilinia species on stone fruits and other Rosaceae plants, such as Monilinia laxa, Monilinia fructicola, and Monilinia fructigena (synonym Monilia species: blossom blight and twig blight, brown rot); Mycosphaerella species on cereals, bananas, soft fruits, and peanuts, such as Mycosphaerella graminicola on wheat (anamorph: Zymoseptoria tritici, previously known as Septoria tritici: Septoria leaf blotch), or Mycosphaerella fijiensis on bananas (synonym Pseudocercospora fijiensis: black Sigatoka disease) and Mycosphaerella musicola, Mycosphaerella arachidicola on peanuts (synonym M. arachidis or Cercospora arachidis), Mycosphaerella berkeleyi, Mycosphaerella pisi on peas, and Mycosphaerella brassiciola on Brassica; Peronospora species on cabbages (e.g., Peronospora brassicae), oilseed rape (e.g., Peronospora parasitica), onions (e.g., Peronospora destructor), tobacco (Peronospora tabacina), and soybeans (e.g., Peronospora manshurica) (downy mildew); Phakopsora pachyrhizi and Phakopsora meibomiae (soybean rust) on soybeans; Phialophora species, such as on vines (e.g., Phialophora tracheiphila and Phialophora tetraspora) and soybeans (e.g., Phialophora sojaegregata): stem rot); Phoma lingam (synonyms Leptosphaeria biglobosa and L. maculans: root and stem rot) on rape and cabbage, and Phoma betae (root rot, leaf spot and damping-off) on sugar beet, as well as P. zeae-maydis (synonym Phyllostica zeae) on maize; Phomopsis species on sunflower, vines (e.g. P. viticola: shoot and leaf spot) and soybean (e.g. stem rot: P. phaseoli, teleomorph: Diaporthe phaseolorum); Physoderma maydis (brown spot) on maize; Phytophthora species on various plants (wilting, root, leaf, fruit and stem rot), such as red pepper and gourd (e.g. P. capsici), soybean (e.g. P. megasperma, synonym P. sojae), potato and tomato (e.g. P. infestans: late blight) and broad-leaved trees (e.g. P. ramorum: sudden oak death); Plasmodiophora brassicae (club root) on cabbage, rape, radish and other plants; Plasmopara species, such as P. viticola (downy mildew of grapevine) on vines and P. halstedii on sunflower; Podosphaera species (powdery mildew) on Rosaceae plants, hops, pome and soft fruits, such as P. leucotricha on apple and P. xanthii on gourd; Polymyxa species, such as P. graminis on cereals such as barley and wheat and P. betae on sugar beet, and virus diseases transmitted thereby; Pseudocercosporella herpotrichoides (synonyms Oculimacula yallundae, O. acuformis: eyespot, teleomorph: Tapesia yallundae) on cereals such as wheat or barley; Pseudoperonospora (downy mildew) on various plants, such as P. cubensis on gourdP. cubensis) or Pseudoperonospora humili on hops; Pseudopezicula tracheiphila (red fire disease or rotbrenner, anamorph: Phialophora) on vines; Puccinia species (rust) on various plants, such as Puccinia triticina (brown rust or leaf rust), Puccinia striiformis (strip rust or yellow rust), Puccinia hordei (dwarf rust), Puccinia graminis (stem rust or black rust), or Puccinia recondita (brown rust or leaf rust) on cereals such as wheat, barley, or rye, Puccinia kuehnii (citrus rust) on sugarcane, and Puccinia asparagi on asparagus; Pyrenopeziza species, such as Pyrenopeziza brassicae on rapeseed; Pyrenophora tritici-repentis (anamorph: Drechslera tritici-repentis) (tan spot) on wheat or Pyrenophora teres (net blotch) on barley; Pyricularia species, such as Pyricularia oryzae (teleomorph: Magnaporthe grisea: rice blast) on rice, and Pyricularia grisea on turfgrass and cereals; Pythium species (damping-off) (e.g., Pythium ultimum or Pythium aphanidermatum) on turfgrass, rice, corn, wheat, cotton, rapeseed, sunflower, soybean, sugar beet, vegetables, and various other plants, and Pythium oligandrum on mushrooms; Ramularia species, such as Ramularia collo-cygni (Ramularia leaf spot, physiological leaf spot) on barley, Ramularia areola (teleomorph: Mycosphaerella areola) on cotton, and Ramularia beticola on sugar beet; Rhizoctonia species on cotton, rice, potato, turfgrass, corn, rapeseed, potato, sugar beet, vegetables, and various other plants, such as Rhizoctonia solani (root and stem rot) on soybean, Rhizoctonia solani (sheath blight) on rice, or Rhizoctonia cerealis on wheat or barley (cerealis) (spring leaf blight of cereals); Rhizopus stolonifer (black mold, soft rot) on strawberries, carrots, cabbages, vines and tomatoes; Rhynchosporium secalis and R. commune (scald) on barley, rye and triticale; Sarocladium oryzae and S. attenuatum (sheath rot) on rice; Sclerotinia species (stem rot or white mold), such as S. minor and S. sclerotiorum, on vegetables and field crops, such as rape, sunflowers (e.g., Sclerotinia) and soybeans; Sclerotium rolfsii (synonym Athelia rolfsii) on soybeans, peanuts, vegetables, corn, cereals and ornamental plants; Septoria species on various plants, such as Septoria glycines (brown spot) on soybeans, Septoria tritici (synonym Zymoseptoria tritici, Septoria leaf blotch) on wheat and Septoria nodorum (synonym Stagonospora nodorum (Stagonospora leaf blotch)) on cereals; Uncinula necator (synonym Erysiphe necator) (powdery mildew, anamorph: Oidium tuckeri) on vines; Setosphaeria species (leaf blight) on corn (e.g., Setosphaeria turcicum, synonym Helminthosporium turcicum) and turfgrass; Sphacelotheca species (smut) on corn (e.g., Sphacelotheca reiliana, synonym Ustilago reiliana: head smut), sorghum and sugarcane; Sphaerotheca fuliginea (synonym Podosphaera xanthii: powdery mildew) on cucurbits; Spongospora subterranea (powdery scab) on potatoes and the virus diseases transmitted thereby; Stagonospora species on cereals, such as Stagonospora nodorum on wheat (S.nodorum) (Stagonospora nodorum leaf blotch, sexual stage: Leptosphaeria nodorum [synonym Phaeosphaeria nodorum], synonym Septoria nodorum); Synchytrium endobioticum on potatoes (potato wart disease); Taphrina species, such as Taphrina deformans on peaches (leaf curl) and Taphrina pruni on plums (plum pocket); Thielaviopsis species on tobacco, pome fruits, vegetables, soybeans and cotton (black root rot), such as Thielaviopsis basicola (synonym Chalara elegans); Tilletia species on cereals (common bunt or stinking smut), such as Tilletia tritici on wheat (synonym Tilletia caries, common bunt) and Tilletia controversa on wheat (dwarf bunt); Trichoderma harzianum on mushrooms; Typhula incarnata on barley or wheat (grey snow mold); Urocystis species, such as Urocystis occulta on rye (stem smut); Uromyces species on vegetables such as kidney beans (e.g., Uromyces appendiculatus, synonym Uromyces phaseoli), sugar beets (e.g., Uromyces betae or Uromyces beticola) and dry beans (e.g., Uromyces vignae, Uromyces pisi, Uromyces viciae-fabae and Uromyces fabae) (rust); Ustilago species on cereals (e.g., Ustilago nuda and Ustilago avenae), maize (e.g., Ustilago maydis: corn smut) and sugar cane (loose smut); apples (e.g., Venturiaspecies of Venturia (scab) on pears; and species of Verticillium (wilt) on various plants such as fruit and ornamental plants, vines, soft fruits, vegetables and field crops, such as V. longisporum on oilseed rape, V. dahliae on strawberries, oilseed rape, potatoes and tomatoes, and V. fungicola on mushrooms; Septoria tritici on cereals.

[0305] Compound I and its compositions are particularly suitable for controlling the causative agents of the following plant diseases: rust on soybeans and cereals (e.g., Phakopsora pachyrhizi and Phakopsora meibomiae on soybeans; Puccinia triticina and Puccinia striiformis on wheat); mildew on specialty crops, soybeans, oilseed rape and sunflowers (e.g., Botrytis cinerea on strawberries and vines, Sclerotinia sclerotiorum, Sclerotinia minor and Sclerotium rolfsii on oilseed rape, sunflowers and soybeans); Fusarium diseases on cereals (e.g., Fusarium culmorum and Fusarium graminearum on wheat); downy mildew on specialty crops (e.g., Plasmopara viticola on vines, Phytophthora infestans on potatoes); powdery mildew on specialty crops and cereals (e.g., Uncinula necator on vines, species of Erysiphe on various specialty crops, Blumeria graminis on cereals); and leaf spot on cereals, soybeans and maize (e.g., Septoria tritici and Septoria nodorum on cereals, Septoria glycines on soybeans, species of Cercospora on maize and soybeans).

[0306] According to one embodiment, compounds I.A-1.1a.B-1 to I.A-1.1a.B-180 are particularly suitable for controlling the causative agents of the plant diseases according to list Z.

[0307] According to one embodiment, compounds I.A-2.1a.B-1 to I.A-2.1a.B-180 are particularly suitable for controlling the causative agents of the plant diseases according to list Z.

[0308] According to one embodiment, compounds I.A-3.1a.B-1 to I.A-3.1a.B-180 are particularly suitable for controlling the causative agents of the plant diseases according to list Z.

[0309] According to one embodiment, compounds I.A-4.1a.B-1 to I.A-4.1a.B-180 are particularly suitable for controlling the causative agents of the plant diseases according to list Z.

[0310] According to one embodiment, compounds I.A-5.1a.B-1 to I.A-5.1a.B-180 are particularly suitable for controlling the pathogenic agents of plant diseases according to list Z.

[0311] According to one embodiment, compounds I.A-6.1a.B-1 to I.A-6.1a.B-180 are particularly suitable for controlling the pathogenic agents of plant diseases according to list Z.

[0312] According to one embodiment, compounds I.A-1.2a.B-1 to I.A-1.2a.B-180 are particularly suitable for controlling the pathogenic agents of plant diseases according to list Z.

[0313] According to one embodiment, compounds I.A-2.2a.B-1 to I.A-2.2a.B-180 are particularly suitable for controlling the pathogenic agents of plant diseases according to list Z.

[0314] According to one embodiment, compounds I.A-3.2a.B-1 to I.A-3.2a.B-180 are particularly suitable for controlling the pathogenic agents of plant diseases according to list Z.

[0315] According to one embodiment, compounds I.A-4.2a.B-1 to I.A-4.2a.B-180 are particularly suitable for controlling the pathogenic agents of plant diseases according to list Z.

[0316] According to one embodiment, compounds I.A-5.2a.B-1 to I.A-5.2a.B-180 are particularly suitable for controlling the pathogenic agents of plant diseases according to list Z.

[0317] According to one embodiment, compounds I.A-6.2a.B-1 to I.A-6.2a.B-180 are particularly suitable for controlling the pathogenic agents of plant diseases according to list Z.

[0318] According to one embodiment, compounds I.A-1.3a.B-1 to I.A-1.3a.B-180 are particularly suitable for controlling the pathogenic agents of plant diseases according to list Z.

[0319] According to one embodiment, compounds I.A-2.3a.B-1 to I.A-2.3a.B-180 are particularly suitable for controlling the pathogenic agents of plant diseases according to list Z.

[0320] According to one embodiment, compounds I.A-3.3a.B-1 to I.A-3.3a.B-180 are particularly suitable for controlling the pathogenic agents of plant diseases according to list Z.

[0321] According to one embodiment, compounds I.A-4.3a.B-1 to I.A-4.3a.B-180 are particularly suitable for controlling the pathogenic agents of plant diseases according to list Z.

[0322] According to one embodiment, compounds I.A-5.3a.B-1 to I.A-5.3a.B-180 are particularly suitable for controlling the pathogenic agents of plant diseases according to list Z.

[0323] According to one embodiment, compounds I.A-6.3a.B-1 to I.A-6.3a.B-180 are particularly suitable for controlling the pathogenic agents of plant diseases according to list Z.

[0324] According to one embodiment, compounds I.A-1.4a.B-1 to I.A-1.4a.B-180 are particularly suitable for controlling the pathogenic agents of plant diseases according to list Z.

[0325] According to one embodiment, compounds I.A-2.4a.B-1 to I.A-2.4a.B-180 are particularly suitable for controlling the pathogenic agents of plant diseases according to list Z.

[0326] According to one embodiment, compounds I.A-3.4a.B-1 to I.A-3.4a.B-180 are particularly suitable for controlling the pathogenic agents of plant diseases according to list Z.

[0327] According to one embodiment, compounds I.A-4.4a.B-1 to I.A-4.4a.B-180 are particularly suitable for controlling the pathogenic agents of plant diseases according to list Z.

[0328] According to one embodiment, compounds I.A-5.4a.B-1 to I.A-5.4a.B-180 are particularly suitable for controlling the pathogenic agents of plant diseases according to list Z.

[0329] According to one embodiment, compounds I.A-6.4a.B-1 to I.A-6.4a.B-180 are particularly suitable for controlling the pathogenic agents of plant diseases according to list Z.

[0330] According to one embodiment, compounds I.A-1.5a.B-1 to I.A-1.5a.B-180 are particularly suitable for controlling the pathogenic agents of plant diseases according to list Z.

[0331] According to one embodiment, compounds I.A-2.5a.B-1 to I.A-2.5a.B-180 are particularly suitable for controlling the pathogenic agents of plant diseases according to list Z.

[0332] According to one embodiment, compounds I.A-3.5a.B-1 to I.A-3.5a.B-180 are particularly suitable for controlling the pathogenic agents of plant diseases according to list Z.

[0333] According to one embodiment, compounds I.A-4.5a.B-1 to I.A-4.5a.B-180 are particularly suitable for controlling the pathogenic agents of plant diseases according to list Z.

[0334] According to one embodiment, compounds I.A-5.5a.B-1 to I.A-5.5a.B-180 are particularly suitable for controlling the pathogenic agents of plant diseases according to list Z.

[0335] According to one embodiment, compounds I.A-6.5a.B-1 to I.A-6.5a.B-180 are particularly suitable for controlling the pathogenic agents of plant diseases according to list Z.

[0336] According to one embodiment, compounds I.A-1.6a.B-1 to I.A-1.6a.B-180 are particularly suitable for controlling the pathogenic agents of plant diseases according to list Z.

[0337] According to one embodiment, compounds I.A-2.6a.B-1 to I.A-2.6a.B-180 are particularly suitable for controlling the pathogenic agents of plant diseases according to list Z.

[0338] According to one embodiment, compounds I.A-3.6a.B-1 to I.A-3.6a.B-180 are particularly suitable for controlling the pathogenic agents of plant diseases according to list Z.

[0339] According to one embodiment, compounds I.A-4.6a.B-1 to I.A-4.6a.B-180 are particularly suitable for controlling the pathogenic agents of plant diseases according to list Z.

[0340] According to one embodiment, compounds I.A-5.6a.B-1 to I.A-5.6a.B-180 are particularly suitable for controlling the pathogenic agents of plant diseases according to list Z.

[0341] According to one embodiment, compounds I.A-6.6a.B-1 to I.A-6.6a.B-180 are particularly suitable for controlling the pathogenic agents of plant diseases according to list Z.

[0342] According to one embodiment, compounds I.A-1.7a.B-1 to I.A-1.7a.B-180 are particularly suitable for controlling the pathogenic agents of plant diseases according to list Z.

[0343] According to one embodiment, compounds I.A-2.7a.B-1 to I.A-2.7a.B-180 are particularly suitable for controlling the pathogenic agents of plant diseases according to list Z.

[0344] According to one embodiment, compounds I.A-3.7a.B-1 to I.A-3.7a.B-180 are particularly suitable for controlling the pathogenic agents of plant diseases according to list Z.

[0345] According to one embodiment, compounds I.A-4.7a.B-1 to I.A-4.7a.B-180 are particularly suitable for controlling the pathogenic agents of plant diseases according to list Z.

[0346] According to one embodiment, compounds I.A-5.7a.B-1 to I.A-5.7a.B-180 are particularly suitable for controlling the pathogenic agents of plant diseases according to list Z.

[0347] According to one embodiment, compounds I.A-6.7a.B-1 to I.A-6.7a.B-180 are particularly suitable for controlling the pathogenic agents of plant diseases according to list Z.

[0348] According to one embodiment, compounds Ex-1 to Ex-92 are particularly suitable for controlling the pathogenic agents of plant diseases according to list Z.

[0349] List Z:

[0350] Species of Albugo (white rust) on ornamental plants, vegetables (e.g., Albugo candida), and sunflowers (e.g., Albugo tragopogonis); species of Alternaria (alternaria leaf spot) on vegetables (e.g., Alternaria dauci or Alternaria porri), oilseed rape (Alternaria brassicicola or Alternaria brassicae), sugar beet (Alternaria tenuis), fruits (e.g., Alternaria grandis), rice, soybeans, potatoes, and tomatoes (e.g., Alternaria solani, Alternaria grandis, or Alternaria alternata), tomatoes (e.g., Alternaria solani or Alternaria alternata), and wheat (e.g., Alternaria triticina); species of Aphanomyces on sugar beet and vegetables; species of Ascochyta on cereals and vegetables, such as Ascochyta tritici (anthracnose) on wheat and Ascochyta hordei on barley; Aureobasidium zeae (synonym Kapatiella zeae) on maize; species of Bipolaris and Drechslera (sexual form: species of Cochliobolus), such as southern leaf blight (Drechslera maydis) or northern leaf blight (Bipolaris zeicola) on maize, such as spot blotch (Bipolaris sorokiniana) on cereals and Bipolaris oryzae on rice and turfgrass; Blumeria graminis (formerly known as Erysiphe graminis) (powdery mildew) on cereals (e.g., wheat or barley); Botrytis cinerea (sexual form: Botryotinia fuckeliana: gray mold) on fruits and berries (e.g., strawberries), vegetables (e.g., lettuce, carrots, celery, and cabbages); Botrytis squamosa or Botrytis allii on the onion family, oilseed rape, ornamental plants (e.g., Botrytis elliptica), vines, forest plants, and wheat; Bremia lactucae (downy mildew) on lettuce; species of Ceratocystis (synonym Ophiostoma) (rot or wilt) on broad-leaved and evergreen trees, such as Ceratocystis ulmi on elmulmi) (Dutch elm disease); maize (e.g., gray leaf spot: Cercospora zeae-maydis), rice, sugar beet (e.g., Cercospora beticola), sugar cane, vegetables, coffee, soybean (e.g., Cercospora sojina or Cercospora kikuchii) and Cercospora species on rice (Cercospora leaf spot); Cladobotryum (synonym Dactylium) species on mushrooms (e.g., Cladobotryum mycophilum).

[0351] (formerly known as Dactylium dendroides), teleomorph: Nectria albertinii, Nectria rosella (synonym Hypomyces rosellus); Cladosporium species on tomato (e.g., C. fulvum: leaf mold) and cereals, e.g., C. herbarum on wheat (black ear); Claviceps purpurea on cereals (ergot); Cochliobolus species (anamorph: Helminthosporium of the genus Bipolaris) on maize (C. carbonum), cereals (e.g., C. sativus, anamorph: B. sorokiniana) and rice (e.g., C. miyabeanus, anamorph: H. oryzae) (leaf spot); Colletotrichum (teleomorph: Glomerella) species on cotton (e.g., C. gossypii), maize (e.g., C. graminicola: anthracnose stalk rot), soft fruits, potato (e.g., C. coccodes: black dot), bean (e.g., C. lindemuthianum), soybean (e.g., C. truncatum or C. gloeosporioides), vegetables (e.g., C. lagenarium or C. capsici), fruits (e.g., C. acutatum), coffee (e.g., C. coffeanum or C. kahawae) and various crops (C. gloeosporioides) (anthracnose); Corticium species, e.g., C. sasakii on rice (sheath blight); Corynespora cassiicola on soybean, cotton and ornamental plants (leaf spot); Cycloconium species, e.g., C. oleaginum on olive trees; fruit trees, vines (e.g., Cylindrocladiumliriodendri), sexual form: Neonectria liriodendri: Black Foot Disease) and Cylindrocarpon species on ornamental plants (such as fruit tree canker or young vine decline, sexual form: Nectria or Neonectria species); Dematophora necatrix on soybeans (sexual form: Rosellinia necatrix) (root and stem rot); Diaporthe species, such as D. phaseolorum on soybeans (damping-off); Drechslera (synonym Helminthosporium, sexual form: Pyrenophora) species on corn, cereals such as barley (e.g., D. teres, net blotch) and wheat (e.g., D. tritici-repentis: tan spot), rice, and turfgrass; Esca (dieback, apoplexy) on vines, caused by Formitiporia punctata (synonym Phellinus punctata), F. mediterranea, Phaeomoniella chlamydospora (previously known as Phaeoacremonium chlamydosporum), Phaeoacremonium aleophilum, and / or Botryosphaeria obtusa; Elsinoe species on pome fruits (E. pyri), soft fruits (E. veneta: anthracnose), and vines (E. ampelina: anthracnose); Entyloma oryzae on rice (leaf smut); Epicoccum species on wheat (black mold); Erysiphe betae on sugar beets, Erysiphe pisi on vegetables (such as peas), for example, Erysiphe cichoracearum on cucurbits (such as gourds), cabbage, rape (such as Erysiphe cruciferarum),species of Erysiphe (powdery mildew) on cruciferarum); Eutypa lata (Eutypa canker or dieback, anamorph: Cytosporina lata, synonym Libertella blepharis) on fruit trees, vines, and ornamental trees; species of Exserohilum (synonym Helminthosporium) on maize (e.g., Exserohilum turcicum); species of Fusarium (teleomorph: Gibberella) on various plants (wilt, root or stem rot), such as Fusarium graminearum or Fusarium culmorum (root rot, scab or head blight) on cereals (e.g., wheat or barley), Fusarium oxysporum on tomato, Fusarium solani (f.sp. glycines, new synonym Fusarium virguliforme) on soybean and F. tucumaniae and F. brasiliense (both causing sudden death syndrome), and Fusarium verticillioides on maize; Gaeumannomyces graminis (take-all) on cereals (e.g., wheat or barley) and maize; species of Gibberella on cereals (e.g., Gibberella zeae) and rice (e.g., Gibberella fujikuroi: Bakanae disease); Glomerella cingulata on vines, pome fruits and other plants and Glomerella gossypii on cotton; Grainstaining complex on rice; Guignardia bidwellii (black rot) on vines; species of Gymnosporangium on Rosaceae plants and junipers, such as Gymnosporangium sabinae (rust) on pears; species of Helminthosporium (synonym Drechslera, teleomorph: Cochliobolus) on maize, cereals, potatoes and rice; species of Hemileia, such as Hemileia vastatrix on coffeevastatrix) (coffee leaf rust); Isariopsis clavispora (synonym Cladosporium vitis) on vines; Macrophomina phaseolina (synonym Macrophomina phaseoli) (root and stem rot) on soybeans and cotton; Microdochium nivale (synonym Fusarium nivale) (pink snow mold) on cereals (e.g., wheat or barley); Microsphaera diffusa (powdery mildew) on soybeans; Monilinia species on stone fruits and other Rosaceae plants, such as Monilinia laxa, Monilinia fructicola, and Monilinia fructigena (synonym Monilia species: blossom blight and twig blight, brown rot); Mycosphaerella species on cereals, bananas, soft fruits, and peanuts, such as Mycosphaerella graminicola on wheat (anamorph: Zymoseptoria tritici, previously known as Septoria tritici: Septoria leaf blotch), or Mycosphaerella fijiensis on bananas (synonym Pseudocercospora fijiensis: black Sigatoka disease) and Mycosphaerella musicola, Mycosphaerella arachidicola on peanuts (synonym M. arachidis or Cercospora arachidis), Mycosphaerella berkeleyi, Mycosphaerella pisi on peas, and Mycosphaerella brassiciola on Brassica; Peronospora species on cabbages (e.g., Peronospora brassicae), oilseed rape (e.g., Peronospora parasitica), onions (e.g., Peronospora destructor), tobacco (Peronospora tabacina), and soybeans (e.g., Peronospora manshurica) (downy mildew); Phakopsora pachyrhizi and Phakopsora meibomiae on soybeans (soybean rust); Phialophora species, such as on vines (e.g., Phialophora tracheiphila and Phialophora tetraspora) and soybeans (e.g., Phialophora sojaegregata): stem rot); Phoma lingam (synonyms Leptosphaeria biglobosa and L. maculans: root and stem rot) on rape and cabbage, and Phoma betae (root rot, leaf spot and damping-off) on sugar beet, and P. zeae-maydis (synonym Phyllostica zeae) on maize; Phomopsis species on sunflower, vines (e.g. P. viticola: vine and leaf spot) and soybean (e.g. stem rot: P. phaseoli, teleomorph: Diaporthe phaseolorum); Physoderma maydis (brown spot) on maize; Phytophthora species on various plants (wilting, root, leaf, fruit and stem rot), such as red pepper and gourd (e.g. P. capsici), soybean (e.g. P. megasperma, synonym P. sojae), potato and tomato (e.g. P. infestans: late blight) and broad-leaved trees (e.g. P. ramorum: sudden oak death); Plasmodiophora brassicae (club root) on cabbage, rape, radish and other plants; Plasmopara species, such as P. viticola (downy mildew of grapevine) on vines and P. halstedii on sunflower; Podosphaera species (powdery mildew) on Rosaceae plants, hops, pome and soft fruits, such as P. leucotricha on apple and P. xanthii on gourd; Polymyxa species, such as P. graminis on cereals such as barley and wheat and P. betae on sugar beet, and virus diseases transmitted thereby; Pseudocercosporella herpotrichoides (synonyms Oculimacula yallundae, O. acuformis: eyespot, teleomorph: Tapesia yallundae) on cereals such as wheat or barley; Pseudoperonospora (downy mildew) on various plants, such as P. cubensis on gourdP. cubensis) or P. humili on hops; Pseudopezicula tracheiphila (red fire disease or rotbrenner, anamorph: Phialophora) on vines; Puccinia species (rust) on various plants, such as P. triticina (brown rust or leaf rust) on cereals such as wheat, barley or rye, P. striiformis (strip rust or yellow rust), P. hordei (dwarf rust), P. graminis (stem rust or black rust) or P. recondita (brown rust or leaf rust), P. kuehnii (citrus rust) on sugarcane and P. asparagi on asparagus; Pyrenopeziza species, such as P. brassicae on rape; Pyrenophora tritici-repentis (anamorph: Drechslera tritici-repentis) (tan spot) on wheat or P. teres (net blotch) on barley; Pyricularia species, such as P. oryzae (teleomorph: Magnaporthe grisea: rice blast) on rice, and P. grisea on turfgrass and cereals; Pythium species (damping-off) (e.g., P. ultimum or P. aphanidermatum) on turfgrass, rice, corn, wheat, cotton, rape, sunflower, soybean, sugar beet, vegetables and various other plants, and P. oligandrum on mushrooms; Ramularia species, such as R. Collo-cygni (Ramularia leaf spot, physiological leaf spot) on barley, R. areola (teleomorph: Mycosphaerella areola) on cotton and R. beticola on sugar beet; Rhizoctonia species on cotton, rice, potato, turfgrass, corn, rape, potato, sugar beet, vegetables and various other plants, such as R. solani (root and stem rot) on soybean, R. solani (sheath blight) on rice, or R. cerealis on wheat or barley (cerealis) (spring leaf blight of cereals); Rhizopus stolonifer (black mold, soft rot) on strawberries, carrots, cabbages, vines, and tomatoes; Rhynchosporium secalis and R. commune (scald) on barley, rye, and triticale; Sarocladium oryzae and S. attenuatum (sheath rot) on rice; Sclerotinia species (stem rot or white mold), such as S. minor and S. sclerotiorum, on vegetables and field crops, e.g., rape, sunflower (e.g., S. sclerotiorum), and soybeans; Sclerotium rolfsii (synonym Athelia rolfsii) on soybeans, peanuts, vegetables, corn, cereals, and ornamental plants; Septoria species on various plants, e.g., Septoria glycines (brown spot) on soybeans, Septoria tritici (synonym Zymoseptoria tritici, Septoria leaf blotch) on wheat, and Septoria nodorum (synonym Stagonospora nodorum (Stagonospora leaf blotch)) on cereals; Uncinula necator (synonym Erysiphe necator) (powdery mildew, anamorph: Oidium tuckeri) on vines; Setosphaeria species (leaf blight) on corn (e.g., Setosphaeria turcicum, synonym Helminthosporium turcicum) and turfgrass; Sphacelotheca species (smut) on corn (e.g., Sphacelotheca reiliana, synonym Ustilago reiliana: head smut), sorghum, and sugarcane; Sphaerotheca fuliginea (synonym Podosphaera xanthii: powdery mildew) on cucurbits; Spongospora subterranea (powdery scab) on potatoes and the virus diseases transmitted thereby; Stagonospora species on cereals, e.g., Stagonospora nodorum on wheat, S.nodorum) (Stagonospora nodorum, sexual stage: Leptosphaeria nodorum [synonym Phaeosphaeria nodorum], synonym Septoria nodorum); Synchytrium endobioticum on potatoes (potato wart disease); Taphrina species, such as Taphrina deformans on peaches (leaf curl) and Taphrina pruni on plums (plum pocket); Thielaviopsis species on tobacco, pome fruits, vegetables, soybeans and cotton (black root rot), such as Thielaviopsis basicola (synonym Chalara elegans); Tilletia species on cereals (common bunt or stinking smut), such as Tilletia tritici on wheat (synonym Tilletia caries, common bunt) and Tilletia controversa on wheat (dwarf bunt); Trichoderma harzianum on mushrooms; Typhula incarnata on barley or wheat (grey snow mold); Urocystis species, such as Urocystis occulta on rye (stem smut); Uromyces species on vegetables such as beans (e.g., Uromyces appendiculatus, synonym Uromyces phaseoli), sugar beets (e.g., Uromyces betae or Uromyces beticola) and dry beans (e.g., Uromyces vignae, Uromyces pisi, Uromyces viciae-fabae and Uromyces fabae) (rust); Ustilago species on cereals (e.g., Ustilago nuda and Ustilago avenae), maize (e.g., Ustilago maydis: corn smut) and sugar cane (loose smut); apples (e.g., Venturiaspecies of Venturia (scab) on pears; and species of Verticillium (wilt) on a variety of plants such as fruit and ornamental plants, vines, soft fruits, vegetables and field crops, such as V. longisporum on oilseed rape, V. dahliae on strawberries, oilseed rape, potatoes and tomatoes, and V. fungicola on mushrooms; Septoria tritici on cereals.

[0352] Compound I and its compositions are also suitable for controlling harmful microorganisms in the protection of stored products or harvested crops and in the protection of materials, respectively.

[0353] The term "stored products or harvested crops" should be understood to mean natural substances of plant or animal origin and their processed forms required for long-term protection. Stored products of plant origin, such as stalks, leaves, tubers, seeds, fruits or grains, can be protected in the freshly harvested state or in processed forms such as pre-dried, moistened, ground, milled, pressed or baked (this processing is also referred to as post-harvest treatment). Also falling under the definition of stored products is wood, whether in the form of logs, such as construction timber, transmission towers and fences, or in the form of finished products, such as furniture or objects made of wood. Stored products of animal origin are hides, leather, furs, hairs, etc. Preferably, "stored products" should be understood to mean natural substances of plant origin and their processed forms, more preferably fruits and their processed forms, such as pome fruits, stone fruits, soft fruits and citrus fruits and their processed forms, where the application of Compound I and its compositions can also prevent adverse effects such as rot, discoloration or mould.

[0354] The term "protection of materials" should be understood to mean protecting technical and non-living materials such as adhesives, glues, wood, paper, cardboard, textiles, leather, paint dispersions, plastics, cooling lubricants, fibres or fabrics against infestation and damage by harmful microorganisms such as fungi and bacteria.

[0355] When used in the protection of materials or stored products, the amount of active substance applied depends on the type of application area and the desired effect. The amount usually applied in the protection of materials is 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active substance per cubic metre of treated material.

[0356] Compound I and its compositions can be used respectively to improve the health of plants. The invention also relates to a method for improving the health of plants by treating plants, their propagation materials and / or the sites where plants are growing or will grow with effective amounts of Compound I and its compositions, respectively.

[0357] The term "plant health" should be understood to denote the condition of plants and / or their products, which is determined by a plurality of parameters, either alone or in combination with each other, such as yield (e.g., increased biomass and / or increased content of valuable constituents), plant vigor (e.g., improved plant growth and / or greener leaves ("greening effect")), quality (e.g., improved content or composition of certain constituents), and tolerance to abiotic and / or biotic stress. The parameters determining the plant health condition as defined above can be interdependent or can influence each other.

[0358] Compound I is used as such or in the form of a composition by treating fungi, plants, plant propagation materials (such as seeds), soil, surfaces, materials, or rooms to be protected against fungal attack with a fungicidally effective amount of the active substance. The application can be carried out before and after the plants, plant propagation materials (such as seeds), soil, surfaces, materials, or rooms are infected with fungi.

[0359] The agrochemical composition comprises a fungicidally effective amount of Compound I. The term "fungicidally effective amount" denotes an amount of the composition or Compound I which is sufficient for controlling harmful fungi in the protection of cultivated plants, or of stored products or harvests, or of materials, and which does not cause substantial damage to the treated plants, the treated stored products or harvests, or to the treated materials. Such an amount can vary within a wide range and depends on various factors, such as the fungal species to be controlled, the cultivated plants, stored products, harvests or materials to be treated, the climatic conditions, and the specific Compound I used.

[0360] Plant propagation materials can be prophylactically treated with Compound I itself or with a composition comprising at least one Compound I at the time of planting or transplanting or before planting or transplanting.

[0361] When used in plant protection, depending on the type of desired effect, the amount of the active substance applied is 0.001 to 2 kg / ha, preferably 0.005 to 2 kg / ha, more preferably 0.05 to 0.9 kg / ha, and especially 0.1 to 0.75 kg / ha.

[0362] In the treatment of plant propagation materials (such as seeds), for example by dusting, coating or soaking, an amount of the active substance of generally 0.1 to 1000 g, preferably 1 to 1000 g, more preferably 1 to 100 g, and most preferably 5 to 100 g per 100 kg of plant propagation materials (preferably seeds) is required.

[0363] The user generally applies the agrochemical composition by means of a pre-application device, a knapsack sprayer, a spray tank, a crop spraying aircraft, or an irrigation system. Generally, the agrochemical composition is made up with water, buffer solutions, and / or additional adjuvants to the desired application concentration, and thus a ready-to-use spray liquid or agrochemical composition according to the invention is obtained. Generally, 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquid are applied per hectare of agricultural useful area.

[0364] Compound I, its N-oxides and salts can be converted into common types of agrochemical compositions, such as solutions, emulsions, suspensions, dusts, powders, pastes, granules, tablets, capsules, and mixtures thereof. Examples of composition types (see also "Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 6th Edition, May 2008, CropLife International) are suspensions (e.g., SC, OD, FS), emulsifiable concentrates (e.g., EC), emulsions (e.g., EW, EO, ES, ME), capsules (e.g., CS, ZC), pastes, pills, wettable powders or powders (e.g., WP, SP, WS, DP, DS), tablets (e.g., BR, TB, DT), granules (e.g., WG, SG, GR, FG, GG, MG), insecticidal articles (e.g., LN), and gel formulations (e.g., GF) for treating plant propagation materials such as seeds. These compositions are prepared in a known manner, such as described by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005. The invention also relates to an agrochemical composition comprising an adjuvant and at least one compound I.

[0365] Suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesives, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, fungicides, antifreezes, antifoaming agents, colorants, tackifiers, and binders.

[0366] Suitable solvents and liquid carriers are water and organic solvents such as medium to high boiling mineral oil fractions such as kerosene, diesel oil; oils of vegetable or animal origin; aliphatic hydrocarbons, cycloaliphatic hydrocarbons and aromatic hydrocarbons such as toluene, paraffin wax, tetrahydronaphthalene and alkylated naphthalenes; alcohols such as ethanol, propanol, butanol, benzyl alcohol, cyclohexanol, ethylene glycol; DMSO; ketones such as cyclohexanone; esters such as lactates, carbonates, fatty acid esters, γ-butyrolactone; fatty acids; phosphonates; amines; amides such as N-methylpyrrolidone, fatty acid dimethylamide; and mixtures thereof.

[0367] 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 plant origin such as cereal flour, bark powder, wood powder, nut shell powder and mixtures thereof.

[0368] 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, Volume 1: Emulsifiers & Detergents, McCutcheon’s Directories, Glen Rock, USA, 2008 (International Edition or North American Edition).

[0369] Suitable anionic surfactants are alkali metal salts, alkaline earth metal salts or ammonium salts of sulfonates, sulfates, phosphates, carboxylates and mixtures thereof. Examples of sulfonates are alkylaryl sulfonates, diphenyl sulfonates, α-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecylbenzene and tridecylbenzene, sulfonates of naphthalene 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 alcohols or alkylphenol ethoxylates.

[0370] Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, glycosyl surfactants, polymeric surfactants and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters that have been alkoxylated with 1 to 50 equivalents of alkylene oxide. Ethylene oxide and / or propylene oxide can be used for alkoxylation, preferably ethylene oxide. 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 glycerol monoesters. Examples of glycosyl surfactants are sorbitan, ethoxylated sorbitan, sucrose and glucose esters or alkyl polyglucosides. Examples of polymeric surfactants are homologues or copolymers of vinylpyrrolidone, vinyl alcohol or vinyl acetate.

[0371] Suitable cationic surfactants are quaternary ammonium surfactants, such as quaternary ammonium compounds having one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkyl betaines and imidazolines. Suitable block polymers are A-B or A-B-A type block polymers comprising polyethylene oxide and polypropylene oxide blocks, or A-B-C type block polymers comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are polyacrylic acid or alkali metal salts of polyacid comb polymers. Examples of polybases are polyvinylamine or polyethylenamine.

[0372] Suitable adjuvants are compounds which themselves have negligible pesticidal activity or even no pesticidal activity and which can enhance the biological performance of Compound I against the target. Examples are surfactants, mineral oils or vegetable oils and other adjuvants. Further examples are listed in Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, Chapter 5.

[0373] Suitable thickeners are polysaccharides (such as xanthan gum, carboxymethyl cellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates.

[0374] Suitable fungicides are bronopol and isothiazolone derivatives, such as alkyl isothiazolones and benzisothiazolones.

[0375] Suitable antifreezes are ethylene glycol, propylene glycol, urea, and glycerol.

[0376] Suitable defoamers are silicones, salts of long-chain alcohols, and fatty acids.

[0377] Suitable colorants (such as red, blue, or green) are poorly water-soluble pigments and water-soluble dyes. Examples are inorganic colorants (such as iron oxide, titanium oxide, iron hexacyanoferrate) and organic colorants (such as alizarin, azo, and phthalocyanine colorants).

[0378] Suitable thickening agents or binders are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, polyacrylates, biological waxes or synthetic waxes, and cellulose ethers.

[0379] Agrochemical compositions generally contain from 0.01% to 95% by weight, preferably from 0.1% to 90% by weight, more preferably from 1% to 70% by weight, and especially from 10% to 60% by weight of an active ingredient (such as at least one compound I). Agrochemical compositions generally contain from 5% to 99.9% by weight, preferably from 10% to 99.9% by weight, more preferably from 30% to 99% by weight, and especially from 40% to 90% by weight of at least one adjuvant. The active ingredient (such as compound I) is used in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectra).

[0380] For the purpose of treating plant propagation material, especially seeds, solutions for seed treatment (LS), suspension emulsions (SE), flowable concentrates (FS), dry treatment powders (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC), and gels (GF) are generally used. After dilution 2 to 10 times, the concentration of the active ingredient in the ready-to-use formulation of the composition in question is from 0.01% to 60% by weight, preferably from 0.1% to 40% by weight. Application can be carried out before or during sowing. Methods for applying compound I and its compositions to plant propagation material, especially seeds, respectively, include dressing, coating, granulation, dusting, soaking, and in-furrow application methods. Preferably, compound I or its composition is applied to the plant propagation material separately by a method that does not induce germination, such as by dressing, granulation, coating, and dusting.

[0381] Various types of oils, wetting agents, adjuvants, fertilizers or micronutrients, as well as additional biocides (such as fungicides, growth regulators, herbicides, insecticides, safeners) can be added to Compound I or its composition as a premix, or added just prior to use (tank mix). These reagents can be admixed with the composition according to the invention in a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.

[0382] A biocide is generally a chemical or biological agent (such as a pesticidal active ingredient, compound, composition, virus, bacterium, antimicrobial or disinfectant) that prevents, disables, kills or otherwise frustrates pests by its effects. Target pests can include insects, plant pathogens, weeds, mollusks, birds, mammals, fish, nematodes (roundworms) and microorganisms that damage property, cause nuisances, spread diseases or are vectors of diseases. The term "biocide" also includes plant growth regulators that alter 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 the drying of living tissue, such as the above-ground parts of unwanted plants; plant activators that activate plant physiological functions to defend against certain pests; safeners that reduce the unwanted herbicidal effects of biocides on crop plants; and plant growth promoters that affect plant physiological functions, for example, to enhance plant growth, biomass, yield or any other quality parameter of the harvestable items of crop plants.

[0383] Biopesticides are defined as pesticidal agents based on microorganisms (bacteria, fungi, viruses, nematodes, etc.) or in the form of natural products (compounds such as metabolites, proteins or extracts from biological or other natural sources) (U.S. Environmental Protection Agency: http: / / www.epa.gov / pesticides / biopesticides / ). Biopesticides fall into two main categories, microbial and biochemical pesticides:

[0384] (1) Microbial pesticides consist of bacteria, fungi or viruses (and usually include metabolites produced by bacteria and fungi). Entomopathogenic nematodes are also classified as microbial pesticides, although they are multicellular.

[0385] (2) Biochemical pesticides are naturally occurring substances that control pests or provide other crop protection uses as defined below, but are relatively non-toxic to mammals.

[0386] Mixing compound I or a composition containing them, in the form of use as a fungicide, with other fungicides often results in an expansion of the fungicidal activity spectrum or prevents the development of fungicide resistance. In addition, in many cases, a synergistic effect (synergistic mixture) is obtained.

[0387] The following list of pest control agents II that can be used in combination with compound I is intended to illustrate possible combinations but does not limit them:

[0388] A) Respiratory inhibitors

[0389] - At Q o Site complex III inhibitors: azoxystrobin (A.1.1), methoxyacrylic acid ester (A.1.2), caryomycin (A.1.3), enestroburin (A.1.4), enoxastrobin (A.1.5), enoxamyl (A.1.6), fenoxystrobin / flufenoxystrobin (A.1.7), fluoxastrobin (A.1.8), kresoxim-methyl (A.1.9), mandestrobin (A.1.10), metominostrobin (A.1.11), orysastrobin (A.1.12), picoxystrobin (A.1.13), pyraclostrobin (A.1.14), pyribencarb (A.1.15), pyributicarb (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), pyrimethanil (A.1.19), triclopyricarb / chlorodincarb (A.1.20), fenamidone (A.1.21), fenamidone (A.1.21), methyl-N-[2-[(1,4-dimethyl-5-phenyl-pyrazol-3-yl)oxymethyl]phenyl]-N-methoxy-carbamate (A.1.22), tetraconazole (A.1.25), (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-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), pyrimidifen (A.1.36), picoxystrobin (A.1.37), 2-(o-((2,5-dimethylphenyl-oxymethylene)phenyl)-3-methoxy-acrylic acid methyl ester (A.1.38);

[0390] - At Q iComplex III inhibitors at the site: Cyazofamid (A.2.1), Indaziflam (A.2.2), [(6S,7R,8R)-8-benzyl-3-[(3-hydroxy-4-methoxytetrahydrobenzoxazepin-2-one)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl] 2-methylpropanoate (A.2.3), Fenpicoxamid (A.2.4), Picoxystrobin (A.2.5), Metarylpicoxamid (A.2.6); - Complex II inhibitors: Benodanil (A.3.1), Benzovindiflupyr (A.3.2), Bixafen (A.3.3), Boscalid (A.3.4), Carboxin (A.3.5), Dimethomorph (A.3.6), Fluxapyroxad (A.3.7), Flutolanil (A.3.8), Fluxametamide (A.3.9), Furametpyr (A.3.10), Iprovalicarb (A.3.11), Isopyrazam (A.3.12), Metsulfovax (A.3.13), Oxycarboxin (A.3.14), Fluxazolamide (A.3.15), Pyriofenone (A.3.16), Fluxametamide (A.3.17), Biphenylpyrazoxamide (A.3.18), Fluxapyroxad (A.3.19), Phyllodyl (A.3.20), Thifluzamide (A.3.21), Inpyrfluxam (A.3.22), Pyrapropoyne (A.3.23), Fluindapyr (A.3.28), N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide (A.3.29), (E)-methyl 2-[2-[(5-cyano-2-methylphenoxy)methyl]phenyl]-3-methoxyprop-2-enoate (A.3.30), Isoflucypram (A.3.31), 2-(difluoromethyl)-N-(1,1,3-trimethylinden-4-yl)tetrahydro-1,3-benzoxazine-3-carboxamide (A.3.32), 2-(difluoromethyl)-N-[(3R)-1,1,3-trimethylinden-4-yl]tetrahydro-1,3-benzoxazine-3-carboxamide (A.3.33), 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethylinden-4-yl)tetrahydro-1,3-benzoxazine-3-carboxamide (A.3.34), 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethylinden-4-yl]tetrahydro-1,3-benzoxazine-3-carboxamide (A.3.35)

[0391] -3-formamide (A.3.35), 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indan-4-yl)tetrahydrobenzoxazine -3-formamide (A.3.36), 2-(difluoromethyl)-N-[(3R)-1,1-dimethyl-3-propyl-indan-4-yl]tetrahydrobenzoxazine -3-formamide (A.3.37), 2-(difluoromethyl)-N-(3-isobutyl-1,1-dimethyl-indan-4-yl)tetrahydrobenzoxazine -3-formamide (A.3.38), 2-(difluoromethyl)-N-[(3R)-3-isobutyl-1,1-dimethyl-indan-4-yl]tetrahydrobenzoxazine -3-formamide (A.3.39), trifluoropyridinamine (A.3.24);

[0392] -Other respiratory inhibitors: diflurin (A.4.1); Nitrophenyl derivatives: binapacryl (A.4.2), chlorbenside (A.4.3), dinocap (A.4.4), fluazinam (A.4.5), dicofol (A.4.6), ferimzone (A.4.7); Organometallic compounds: triphenyltin salts, such as triphenyltin acetate (A.4.8), triphenyltin chloride (A.4.9) or triphenyltin hydroxide (A.4.10); amisulbrom (A.4.11); silthiofam (A.4.12);

[0393] B) Sterol biosynthesis inhibitors (SBI fungicides)

[0394] -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), 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), Triadimefon (B.1.27), Triadimenol (B.1.28), Tricyclazole (B.1.29), Uniconazole (B.1.30), 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-(trifluoromethoxy)phenyl]-2-pyridyl]propan-2-ol (B.1.32), 4-[[6-[2-(2,4-Difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile (B.1.33), Ipfentrifluconazole (B.1.37), Chlorfluzolam (B.1.38), (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), Piracarbolid (B.1.45), Prochloraz (B.1.46), Triflumizole (B.1.47); Pyrimidines, Tetrahydrobenzoxazines Classes, piperazines: fenarimol (B.1.49), pyrifenox (B.1.50), triforine (B.1.51), [3-(4-chloro-2-fluorophenyl)-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]benzonitrile (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);

[0395] -δ14-reductase inhibitors: 4-dodecyl-2,6-dimethylmorpholine (aldimorph) (B.2.1), dodemorph (B.2.2), dodemorph acetate (B.2.3), fenpropimorph (B.2.4), pyridinitril (B.2.5), fenpropidin (B.2.6), tridemorph (B.2.7), spiroxamine (B.2.8);

[0396] -3-ketoreductase inhibitors: fenhexamid (B.3.1);

[0397] -Other sterol biosynthesis inhibitors: dichlobutrazol (B.4.1);

[0398] C) Nucleic acid synthesis inhibitors

[0399] -Phenylamide or acylamino acid fungicides: benalaxyl (C.1.1), benalaxyl-M (C.1.2), kiralaxyl (C.1.3), metalaxyl (C.1.4), metalaxyl-M (C.1.5), furmecyclox (C.1.6), oxadixyl (C.1.7);

[0400] -Other nucleic acid synthesis inhibitors: hymexazol (C.2.1), octhilinone (C.2.2), oxolinic acid (C.2.3), ethirimol sulfate (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);

[0401] D) Cell division and cytoskeleton inhibitors

[0402] - Tubulin inhibitors: benomyl (D.1.1), carbendazim (D.1.2), fuberidazole (D1.3), thiabendazole (D.1.4), thiophanate-methyl (D.1.5), pyridachlometyl (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-methylthio-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-methylthio-N-propyl-acetamide (D.1.14), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)-2-methylthio-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);

[0403] - Other cell division inhibitors: diethofencarb (D.2.1), ethaboxam (D.2.2), fenfuram (D.2.3), fluopicolide (D.2.4), zoxamide (D.2.5), metrafenone (D.2.6), pyriofenone (D.2.7), cyanotilide (D.2.8);

[0404] E) Amino acid and protein synthesis inhibitors

[0405] - Methionine synthesis inhibitors: cyprodinil (E.1.1), fenarimol (E.1.2), pyrimethanil (E.1.3);

[0406] - Protein synthesis inhibitors: blastcidin-S (E.2.1), kasugamycin (E.2.2), kasugamycin hydrochloride hydrate (E.2.3), validamycin (E.2.4), streptomycin (E.2.5), oxytetracycline (E.2.6);

[0407] F) Signal transduction inhibitors

[0408] - MAP / Histidine Kinase Inhibitors: fluoroimid (F.1.1), iprodione (F.1.2), procymidone (F.1.3), vinclozolin (F.1.4), fludioxonil (F.1.5);

[0409] - G - Protein Inhibitors: quinoxyfen (F.2.1);

[0410] G) Lipid and Membrane Synthesis Inhibitors

[0411] - Phospholipid Biosynthesis Inhibitors: edifenphos (G.1.1), isoprothiolane (G.1.2), bilanafos (G.1.3), isoprobenfos (G.1.4);

[0412] - Lipid Peroxidation: dichlofluanid (G.2.1), quintozene (G.2.2), tecnazene (G.2.3), tolclofos - methyl (G.2.4), biphenyl (G.2.5), chloroneb (G.2.6), ethaboxam (G.2.7), thiazole zinc (G.2.8);

[0413] - Phospholipid Biosynthesis and Cell Wall Deposition: dimethomorph (G.3.1), flumorph (G.3.2), mandipropamid (G.3.3), pyrimorph (G.3.4), benthiavalicarb - isopropyl (G.3.5), iprovalicarb (G.3.6), valifenalate (G.3.7);

[0414] - Compounds Affecting Cell Membrane Permeability and Fatty Acids: propamocarb (G.4.1);

[0415] - Oxysterol - Binding Protein Inhibitors: flutriafol (G.5.1), fluoxapiprolin (G.5.3), 4 - [1 - [2 - [3 - (difluoromethyl)-5 - methyl - pyrazol - 1 - yl]acetyl]-4 - piperidinyl]-N - tetrahydronaphthalen - 1 - yl - tetrahydrobenzoxazepine - 2 - carboxamide (G.5.4), 4 - [1 - [2 - [3,5 - bis(difluoromethyl)pyrazol - 1 - yl]acetyl]-4 - piperidinyl]-N - tetrahydronaphthalen - 1 - yl - tetrahydrobenzoxazepine - 2 - carboxamide (G.5.5), 4 - [1 - [2 - [3 - (difluoromethyl)-5 - (trifluoromethyl)pyrazol - 1 - yl]acetyl]-4 - piperidinyl]-N - tetrahydronaphthalen - 1 - yl - tetrahydrobenzoxazepine - 2 - carboxamide (G.5.6), 4 - [1 - [2 - [5 - cyclopropyl - 3 - (difluoromethyl)pyrazol - 1 - yl]acetyl]-4 - piperidinyl]-N - tetrahydronaphthalen - 1 - yl - tetrahydrobenzoxazepine - 2 - carboxamide (G.5.7); - 2 - carboxamide (G.5.4), 4 - [1 - [2 - [3,5 - bis(difluoromethyl)pyrazol - 1 - yl]acetyl]-4 - piperidinyl]-N - tetrahydronaphthalen - 1 - yl - tetrahydrobenzoxazepine - 2 - carboxamide (G.5.5), 4 - [1 - [2 - [3 - (difluoromethyl)-5 - (trifluoromethyl)pyrazol - 1 - yl]acetyl]-4 - piperidinyl]-N - tetrahydronaphthalen - 1 - yl - tetrahydrobenzoxazepine - 2 - carboxamide (G.5.6), 4 - [1 - [2 - [5 - cyclopropyl - 3 - (difluoromethyl)pyrazol - 1 - yl]acetyl]-4 - piperidinyl]-N - tetrahydronaphthalen - 1 - yl - tetrahydrobenzoxazepine - 2 - carboxamide (G.5.7); - 2 - carboxamide (G.5.5), 4 - [1 - [2 - [3 - (difluoromethyl)-5 - (trifluoromethyl)pyrazol - 1 - yl]acetyl]-4 - piperidinyl]-N - tetrahydronaphthalen - 1 - yl - tetrahydrobenzoxazepine - 2 - carboxamide (G.5.6), 4 - [1 - [2 - [5 - cyclopropyl - 3 - (difluoromethyl)pyrazol - 1 - yl]acetyl]-4 - piperidinyl]-N - tetrahydronaphthalen - 1 - yl - tetrahydrobenzoxazepine - 2 - carboxamide (G.5.7); - 2 - carboxamide (G.5.6), 4 - [1 - [2 - [5 - cyclopropyl - 3 - (difluoromethyl)pyrazol - 1 - yl]acetyl]-4 - piperidinyl]-N - tetrahydronaphthalen - 1 - yl - tetrahydrobenzoxazepine - 2 - carboxamide (G.5.7); -2-formamide (G.5.7), 4-[1-[2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphthalen-1-yl-1,4-benzoxazepine -2-formamide (G.5.8), 4-[1-[2-[5-(difluoromethyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphthalen-1-yl-1,4-benzoxazepine -2-formamide (G.5.9), 4-[1-[2-[3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphthalen-1-yl-1,4-benzoxazepine -2-formamide (G.5.10), (4-[1-[2-[5-cyclopropyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphthalen-1-yl-1,4-benzoxazepine -2-formamide (G.5.11);

[0416] H) Inhibitors with multi-site action

[0417] - 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);

[0418] - Thio- and dithiocarbamates: ferbam (H.2.1), mancozeb (H.2.2), maneb (H.2.3), metam-sodium (H.2.4), metiram (H.2.5), zinc methyldithiocarbamate (H.2.6), thiram (H.2.7), zineb (H.2.8), zinc dimethyldithiocarbamate (H.2.9);

[0419] - Organochlorine 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, tecnazene (H.3.10), tolylfluanid (H.3.11);

[0420] - Guanidine 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), guazatine-amine (H.4.6), guazatine-amine triacetate (H.4.7), bisoctrimonium benzene sulfonate (H.4.8), dithianon (H.4.9), 2,6-dimethyl-1H,5H-[1,4]dithieno[2,3-c:5,6-c’]dipyrrole-1,3,5,7(2H,6H)-tetrone (H.4.10);

[0421] I) Cell wall synthesis inhibitors

[0422] - Glucan synthesis inhibitors: validamycin (I.1.1), polyoxin (I.1.2);

[0423] - Melanin synthesis inhibitors: pyroquilon (I.2.1), tricyclazole (I.2.2), carpropamid (I.2.3), dicyclomet (I.2.4), blastoxamide (I.2.5);

[0424] J) Plant defense inducers

[0425] - Benzoic acid, S-methyl ester (J.1.1), thiabendazole (J.1.2), isotianil (J.1.3), tiadinil (J.1.4), prohexadione-calcium (J.1.5); Phosphonates: etridiazole (J.1.6), fosetyl-aluminum (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)-1,2,5-thiadiazole-3-carboxamide (J.1.10);

[0426] K) Unknown mode of action

[0427] -Bronopol (K.1.1), BPMC (K.1.2), Cyflufenamid (K.1.3), Cymoxanil (K.1.4), Dazomet (K.1.5), Imibenconazole (K.1.6), Diclocymet (K.1.7), Pyridinitril (K.1.8), Avenge (K.1.9), Avenge - methyl sulfate (K.1.10), Diphenylamine (K.1.11), Ethyl chrysanthemate (K.1.12), Ametoctradin (K.1.13), Flumetover (K.1.14), Sulfuram (K.1.15), Fluopyram (K.1.16), Harpin protein (K.1.17), Sulfosultap (K.1.18), 3,5,6 - Trichloro - 2 - pyridinol (K.1.19), Phthalide (K.1.20), Tolprocarb (K.1.21), Copper quinolate (K.1.22), Propoxyquinoline (K.1.23), Tebufloquin (K.1.24), Phyllachlor (K.1.25), Pyrazophos (K.1.26), N’-(4-(4 - chloro - 3 - trifluoromethyl - phenoxy)-2,5 - dimethyl - phenyl)-N - ethyl - N - methyl - formamidine (K.1.27), N’-(4-(4 - fluoro - 3 - trifluoromethyl - phenoxy)-2,5 - dimethyl - phenyl)-N - ethyl - N - methyl - formamidine (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 - isopropylcyclohexyloxy)-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 - trimethylsilyl - propoxy)phenyl)-N - ethyl - N - methyl - formamidine (K.1.34), N’-(5 - difluoromethyl - 2 - methyl - 4-(3 - trimethylsilyl - propoxy)-phenyl)-N - ethyl - N - methyl - formamidine (K.1.35), 2-(4 - chlorophenyl)-N-[4-(3,4 - dimethoxyphenyl)isoxazol - 5 - yl]-2 - prop - 2 - ynyloxy - acetamide (K.1.36), 3-[5-(4 - chlorophenyl)-2,3 - dimethyl - isoxazolidin - 3 - yl]-tetrahydro - benzoxazine (Picoxystrobin)(K.1.37), 3-[5-(4-methylphenyl)-2,3-dimethyl-isoxazolidin-3-yl]-tetrahydrobenzoxazine (K.1.38), 5-chloro-1-(4,6-dimethoxypyrimidin-2-yl)-2-methyl-1H-benzimidazole (K.1.39), ethyl (Z)-3-amino-2-cyano-3-phenylacrylate (K.1.40), tetraconazole (K.1.41), N-[6-[[(Z)-[(1-methyltetrazol-5-yl)phenylmethylene]amino]oxymethyl]-2-pyridinyl]pentylcarbamate (K.1.42), N-[6-[[(Z)-[(1-methyltetrazol-5-yl)phenylmethylene]amino]oxymethyl]-2-pyridinyl]but-3-ynylcarbamate (K.1.43), ipflufenoquin (K.1.44), quinofumelin (K.1.47), thiabendazole (K.1.48), bromothalonil (K.1.49), 2-(6-benzyl-2-pyridinyl)quinazoline (K.1.50), 2-[6-(3-fluoro-4-methoxyphenyl)-5-methyl-2-pyridinyl]quinazoline (K.1.51), dichlobentiazox (K.1.52), N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylformamidine (K.1.53), amisulbrom (K.1.54), fluoxastrobin (K.1.55), N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxyethoxy)-3-pyridinyl]-N-ethyl-N-methylformamidine (K.1.56), N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethylphenyl]-N-ethyl-N-methylformamidine (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]thiobenzamide (K.1.59), N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide (WO 2018 / 177894, WO 2020 / 212513);

[0428] L) Biocidal pest control agents

[0429] L1) Microbial pest control agents with fungicidal, bactericidal, virucidal and / or plant defense activator activities: Ampelomyces quisqualis, Aspergillus flavus, Aureobasidium pullulans, Bacillus altitudinis, Bacillus amyloliquefaciens, Bacillus amyloliquefaciens subsp. plantarum (also known as Bacillus velezensis), Bacillus megaterium, Bacillus mojavensis, Bacillus mycoides, Bacillus pumilus, Bacillus simplex, Bacillus salarius, Bacillus subtilis, Bacillus subtilis var. amyloliquefaciens, Bacillus velezensis, Candida oleophila, Candida saitoana, Clavibacter michiganensis (phage), Coniothyrium minitans, Cryptocline parasitica, Cryptococcus albidus, Dilophosphora alopecuri, Fusarium oxysporum, Clonostachys rosea f. catenulate (also known as Gliocladium catenulatum), Gliocladium roseum, Lysobacter antibioticus, Lysobacter enzymogenes, Metschnikowia fructicola, Microdochium dimerum, Microsphaeropsis arundinis, Muscodor albus, Paenibacillus alvei, Paenibacillus epiphyticus, Paenibacillus polymyxa, Pantoea agglomerans, Penicillium bilaiae, Phellinus igniarius, Pseudomonas spp., Pseudomonas chlororaphis, Pseudozyma flocculosa, Pichia anomala, Pythium oligandrum, Sphaerodes mycoparasitica, Streptomyces griseoviridis, Streptomyces lydicus, Streptomyces violaceoniger, Talaromyces flavus, Trichoderma asperelloides, Trichoderma asperellum, Trichoderma atroviride, Trichoderma apical, Trichoderma gamasum, Trichoderma harzianum, Trichoderma harmatum, Trichoderma polysporum, Trichoderma stromaticum, Trichoderma virens, Trichoderma viride, Typhula phacorrhiza, Ulocladium oudemansii, Verticillium dahliae, zucchini yellow mosaic virus (avirulent strain);

[0430] L2) Biochemical pest control agents with fungicidal, bactericidal, virucidal and / or plant defense activator activities: harpin proteins, Reynoutria japonica Houtt. extract;

[0431] L3) Microbial pesticidal agents with insecticidal, acaricidal, molluscicidal and / or nematicidal activity: Agrobacterium radiobacter, Bacillus cereus, Bacillus firmus, Bacillus thuringiensis, Bacillus thuringiensis subsp. aizawai, Bacillus thuringiensis subsp. israelensis, Bacillus thuringiensis subsp. galleriae, Bacillus thuringiensis subsp. kurstaki, Bacillus thuringiensis subsp. tenebrionis, Beauveria bassiana, Beauveria brongniartii, Burkholderia species, Chromobacterium subtsugae, Cydia pomonella granulovirus (CpGV), Cryptophlebia leucotreta granulovirus (CrleGV), Flavobacterium species, Helicoverpa armigera nucleopolyhedrovirus (HearNPV), Helicoverpa zea nucleopolyhedrovirus (HzNPV), Helicoverpa zea single nucleocapsid nucleopolyhedrovirus (HzSNPV), Heterorhabditis bacteriophora, Isaria fumosorosea, Lecanicillium longisporum, Lecanicillium muscarium, Metarhizium anisopliae, Metarhizium anisopliae var. anisopliae, Metarhizium anisopliae var. acridum, Nomuraea rileyi, Paecilomyces fumosoroseus, Paecilomyces lilacinus, Paenibacillus popilliae, Pasteuria species, Pasteuria nishizawae, Pasteuria penetrans, Pasteuria ramosa, Pasteuria thornei, Pasteuria usgae, Pseudomonas fluorescens, Spodoptera litura nucleopolyhedrovirus (SpliNPV), Steinernema carpocapsae, Steinernema feltiae, Steinernema sawfly, Streptomyces gilvosporeus, Streptomyces microflavus;

[0432] L4) Biochemical pesticidal agents with insecticidal, acaricidal, molluscicidal, pheromonal and / or nematicidal activity: L-carvone, citral, (E,Z)-7,9-dodecadien-1-yl acetate, ethyl formate, ethyl (E,Z)-2,4-decadienoate (pear ester), (Z,Z,E)-7,11,13-hexadecatrienal, heptyl butyrate, isopropyl myristate, lavandulyl senecioate, cis-jasmone, 2-methyl-1-butanol, methyleugenol, methyl jasmonate, (E,Z)-2,13-octadecadien-1-ol, (E,Z)-2,13-octadecadien-1-yl acetate, (E,Z)-3,13-octadecadien-1-ol, (R)-1-octen-3-ol, termite pheromone (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, Chenopodium ambrosiodes extract, neem oil, Quillay extract;

[0433] L5) Microbial pesticidal agents with plant stress reduction, plant growth regulator, plant growth promotion and / or yield increase activity: Azospirillum amazonense, Azospirillum brasilense, Azospirillum lipoferum, Azospirillum iraquense, Azospirillum halopraeferens, Bradyrhizobium spp., Bradyrhizobium elkanii, Bradyrhizobium japonicum, Bradyrhizobium liaoningense, Bradyrhizobium lupini, Delftia acidovorans, arbuscular mycorrhizal fungi, Mesorhizobium spp., Rhizobium leguminosarum biovar phaseoli, Rhizobium leguminosarum biovar trifolii, Rhizobium leguminosarum biovar viciae, Rhizobium tropici and Sinorhizobium meliloti;

[0434] O) Insecticides from classes O.1 to O.29

[0435] O.1 Acetylcholinesterase (AChE) inhibitors: aldicarb, cotton boll carb, benfuracarb, butanone carb, butanone sulfone carb, carbaryl, carbofuran, butanone carb, ethiofencarb, fenbutacarb, fenthiocarb, furamycin, isoprocarb, methiocarb, methomyl, cypermethrin, oxamycin, pirimicarb, propoxur, thiodicarb, long-acting carb, mixed carb, XMC, methiocarb, triazolam; acephate, methyl pyridinium, ethyl azinphos-methyl, azinphos-methyl, cadusin, chlorpyrifos, chlorpyrifos, chlorpyrifos, methyl chlorpyrifos, chlorpyrifos, chlorpyrifos-S-methyl, diazinon, dichlorvos / DDVP, dimethoate, dimethoate, methyl chlorpyrifos, ethyl Amophos, EPN, ethion, propylphos, fenamiphos, fenamiphos, fenitrothion, fenthion, thiamethoxam, heptenephos, cyanimiphos, isopropylamine, O-(methoxyaminothio-phosphoryl) salicylic acid isopropyl ester, isoxathion, malathion, aphidron, methamidophos, methidathion, cypermethrin, monocrotophos, dibromophos, omethoate, sulfone, parathion, methyl parathion, fenthion, phorate, phosalone, phosmet, phosphamidon, phoxim, methyl pirimiphos, propylbromophos, methoprene, propylthion, pyraclofos, pyridazinphos, quinalphos, butyl pirimiphos, bispyribophos, terbufos, chlorpyrifos, methyl ethylsulfonate, triazophos, trichlorfon, aphidron;

[0436] O.2 GABA-gated chloride channel antagonists: endosulfan, chlordane; ethiprole, fipronil, butenefipronil, pyrafluprole, pyriprole;

[0437] O.3 Sodium channel modulators: flumethrin, allethrin, dextro-cis-trans allethrin, dextro-trans allethrin, bifenthrin, k-bifenthrin, bio-allethrin, bio-allethrin S-cyclopentenyl, bio-resmethrin, acetothrin, cypermethrin, β-cypermethrin, flucythrin, λ-cypermethrin, γ-cypermethrin, cypermethrin, α-cypermethrin, β-cypermethrin, θ-cypermethrin, ζ-cypermethrin, phenothrin, deltamethrin, ene Permethrin, cypermethrin, cypermethrin, cypermethrin, flucythrinate, flucythrinate, tau-fluvalinate, bromofluthrin, tefluthrin, imiprothrin, chlorfluthrin, metofluthrin, methoxyfluthrin, ε-methoxyfluthrin, permethrin, phenothrin, pralothrin, profluthrin, pyrethrin (pyrethrum), pyrethrin, silafluthrin, tefluthrin, kappa-tefluthrin, tetrafluthrin, tetramethrin, tralomethrin, transfluthrin; DDT, methoxy-DDT;

[0438] O.4 Nicotinic acetylcholine receptor (nAChR) agonists: acetamiprid, clothianidin, epoxiconazole, 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-pentylideneaminoguanidine; 1-[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1,2,3,5,6,7-hexahydroimidazo[1,2-a]tetrahydrobenzoxazepine 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-phenolate, (3S)-3-(6-chloro-3-pyridinyl)-8-methyl-5-oxo-6-phenyl-2,3-dihydrothiazolo[3,2-a]pyrimidin-8-ium-7-phenolate, (3S)-8-methyl-5-oxo-6-phenyl-3-pyrimidin-5-yl-2,3-dihydrothiazolo[3,2-a]pyrimidin-8-ium-7-phenolate, (3R)-3-(2-chlorothiazol-5-yl)-8-methyl-5-oxo-6-[3-(trifluoromethyl)phenyl]-2,3-dihydrothiazolo[3,2-a]pyrimidin-8-ium-7-phenolate; (3R)-3-(2-chlorothiazol-5-yl)-6-(3,5-dichlorophenyl)-8-methyl-5-oxo-2,3-dihydrothiazolo[3,2-a]pyrimidin-8-ium-7-phenolate, (3R)-3-(2-chlorothiazol-5-yl)-8-ethyl-5-oxo-6-phenyl-2,3-dihydrothiazolo[3,2-a]pyrimidin-8-ium-7-phenolate;

[0439] O.5 Allosteric activators of nicotinic acetylcholine receptors: spinosad, spinetoram;

[0440] O.6 Chloride channel activators: abamectin, emamectin benzoate, ivermectin, lepimectin, milbemycin;

[0441] O.7 Juvenile hormone mimics: hydroprene, kinoprene, methoprene; fenoxycarb, pyriproxyfen;

[0442] O.8 Various non-specific (multi-site) inhibitors: methyl bromide and other alkyl halides; chloropicrin, sulfuryl fluoride, borax, tartar emetic;

[0443] O.9 Chordotonal organ TRPV channel modulators: pymetrozine, flonicamid;

[0444] O.10 Mite growth inhibitors: clofentezine, hexythiazox, flufenzine; etoxazole;

[0445] O.11 Microbial disrupters of the midgut membrane in insects: 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, Bt crop proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34 / 35Ab1;

[0446] O.12 Mitochondrial ATP synthase inhibitors: diafenthiuron; azocyclotin, cyhexatin, fenbutatin oxide, propargite, chlorfenson;

[0447] O.13 Oxidative phosphorylation uncouplers that interfere via the proton gradient: chlorfenapyr, DNOC, flufenerim;

[0448] O.14 Nicotinic acetylcholine receptor (nAChR) channel blockers: bensultap, cartap, thiocyclam, bisultap;

[0449] O.15 Chitin biosynthesis inhibitor type 0: bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, polyflumuron, flupyrazofos, teflubenzuron;

[0450] O.16 Chitin biosynthesis inhibitor type 1: buprofezin;

[0451] O.17 Molting disrupters: cyromazine;

[0452] O.18 Ecdysone receptor agonists: methoxyfenozide, tebufenozide, halofenozide, fufenozide, chromafenozide;

[0453] O.19 Octopamine receptor agonists: amitraz;

[0454] O.20 Mitochondrial complex III electron transport inhibitors: hydramethylnon, acequinocyl, fluacrypyrim, bifenazate;

[0455] O.21 Mitochondrial Complex I Electron Transport Inhibitors: Fenpyroximate, Fenazaquin, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad; Rotenone;

[0456] 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;

[0457] O.23 Acetyl-CoA Carboxylase Inhibitors: Spirodiclofen, Spiromesifen, Spirotetramat, Methoxyfenozide;

[0458] O.24 Mitochondrial Complex IV Electron Transport Inhibitors: Aluminium Phosphide, Calcium Phosphide, Phosphine, Zinc Phosphide, Cyanides;

[0459] O.25 Mitochondrial Complex II Electron Transport Inhibitors: Cyenopyrafen, Butylflufenpyr;

[0460] O.26 Ryanodine Receptor Modulators: Flubendiamide, Chlorantraniliprole, Cyantraniliprole, Cyclaniliprole, Cyhalodiamide; (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-λ4-sulfanylidene)carbamoyl]phenyl]-2-(3-chloropyridin-2-yl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[4-chloro-2-[(diethyl-λ4-sulfanylidene)carbamoyl]-6-methylphenyl]-2-(3-chloropyridin-2-yl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[4-chloro-2-[(di-2-propyl-λ4-sulfanylidene)carbamoyl]-6-methylphenyl]-2-(3-chloropyridin-2-yl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[4,6-dichloro-2-[(di-2-propyl-λ4-sulfanylidene)carbamoyl]phenyl]-2-(3-chloropyridin-2-yl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[4,6-dibromo-2-[(diethyl-λ4-sulfanylidene)carbamoyl]phenyl]-2-(3-chloropyridin-2-yl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide; 3-chloro-1-(3-chloropyridin-2-yl)-N-[2,4-dichloro-6-[[(1-cyano-1-methylethyl)amino]carbonyl]phenyl]-1H-pyrazole-5-carboxamide; tetrachlorantraniliprole; N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloropyridin-2-yl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide; chlorantraniliprole;

[0461] O.27: Chordotonal organ modulators - undefined target site: flonicamid;

[0462] O.28. Insecticidal compounds with unknown or uncertain mode of action: Cyantraniliprole, Afoxolaner, Azadirachtin, Bifenazate, Bromopropylate, Cyazypyr, Bromopropylate, Chinomethionat, Sodium fluoroaluminate, Cyflumetofen, Dicloran, Dicofol, Clothianidin, Flonicamid, Flupyrazofos, Flufiprole, Fluralaner, Oxythioquinox, Piperonyl butoxide, Pyraclostrobin, Pyrethroid, Thienothiophene, 11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxo-9-aza-dispiro[4.2.4.2]-tetradec-11-ene-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 I-1582; flupyrimin; fluazaindolizine; 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-2-methyl-N-(1-oxothietan-3-yl)benzamide; fluxametamide; 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)propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; 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-dioxolan-2-yl)-6-[2-(3-pyridyl)-5-thiazolyl]-tetrahydrobenzoxazine 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-pyridinyl)thiazol-5-yl]tetrahydrobenzoxazepine -2-carboxamide; N-methylsulfonyl-6-[2-(3-pyridinyl)thiazol-5-yl]tetrahydrobenzoxazepine -2-carboxamide; 1-[(6-chloro-3-pyridinyl)methyl]-1,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitro-imidazo[1,2-a]tetrahydrobenzoxazepine 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-methylethyl)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-methylpropyl)-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-methylpropyl]-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, tyclopyrazoflor; sarolaner; 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-pyridinyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]tetrahydrobenzoxazine; 2-[3-Ethylsulfonyl-5-(trifluoromethyl)-2-pyridinyl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]tetrahydrobenzoxazine Isoxazid, 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; Acynonapyr; Benzpyrimoxan; 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, Oxasulfurol, [(2S,3R,4R,5S,6S)-3,5-dimethoxy-6-methyl-4-propoxytetrahydropyran-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-methyltetrahydropyran-2-yl]N-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate, [(2S,3R,4R,5S,6S)-3,5-dimethoxy-6-methyl-4-propoxytetrahydropyran-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-methyltetrahydropyran-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]methylidenehydrazino]thiazolidin-4-one; 2-(6-chloro-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]tetrahydrobenzoxazine 2-(6-Bromo-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]tetrahydrobenzoxazine 2-(3-Ethylsulfonyl-6-iodo-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]tetrahydrobenzoxazine 2-[3-Ethylsulfonyl-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]tetrahydrobenzoxazine 2-(7-Chloro-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]tetrahydrobenzoxazine 2-(3-Ethylsulfonyl-7-iodo-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]tetrahydrobenzoxazine 3-Ethylsulfonyl-6-iodo-2-[3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridin-2-yl]imidazo[1,2-a]tetrahydrobenzoxazine -8-Carbonitrile, 2-[3-Ethylsulfonyl-8-fluoro-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]tetrahydrobenzoxazine 2-[3-Ethylsulfonyl-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethylsulfinyl)imidazo[4,5-b]tetrahydrobenzoxazine 2-[3-Ethylsulfonyl-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]tetrahydrobenzoxazine 2-(6-Bromo-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-6-(trifluoromethyl)pyrazolo[4,3-c]tetrahydrobenzoxazine

[0463] The active substance known as component 2, its preparation and its activity, for example against harmful fungi, are known (see: http: / / www.alanwood.net / pesticides / ); these substances are commercially available. The compounds described by the IUPAC nomenclature, their preparation and their pesticidal activity are also known (see Can. J. Plant Sci. [Canadian Journal of Plant Science] 48(6), 587-94, 1968; EP-A 141 317; EP-A 152 031; EP-A 226 917; EP-A 243 970; EP-A256503; EP-A 428 941; EP-A 532 022; EP-A 1 028 125; EP-A 1 035 122; EP-A 1 201648; EP-A 1 122 244, JP 2002316902; DE 19650197; DE 10021412; DE 102005009458; US3,296,272; US 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; 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 / 139271, 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, CN 1907024, CN1456054, CN 103387541, CN 1309897, WO 12 / 84812, CN 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, WO 16 / 156241, WO 16 / 162265). Some compounds are identified by their CAS Registry Number, which is divided into three parts by hyphens, the first part consisting of two to seven digits, the second part consisting of two digits, and the third part consisting of a single digit.;

[0464] According to the present invention, the solid material (dry matter) of biopesticides (except for oils such as neem oil, etc.) is considered to be the active ingredient (obtained, for example, in the case of liquid formulations of microbial pesticides after drying or evaporation of the extraction or suspension medium). The weight ratios and percentages used for biological extracts such as soapbark extract are based on the total weight of the dry content (solid material) of the corresponding extract.

[0465] The total weight ratio of a composition containing at least one microbial pesticide in the form of live microbial cells (including dormant forms) can be determined by calculating the total weight of the corresponding active ingredient using the amount of CFU of the corresponding microorganism with the following equation: 1×10 10 CFU is equal to the total weight of one gram of the corresponding active ingredient. Colony forming unit is a measure of live microbial cells. In addition, "CFU" can also be understood as the number of (juvenile) individual nematodes in the case of nematode biopesticides such as Steinernema feltiae.

[0466] In a binary mixture, the weight ratio of component 1) to component 2) generally depends on the properties of the components used and is generally in the range from 1:10,000 to 10,000:1, often in the range from 1:100 to 100:1, frequently in the range from 1:50 to 50:1, preferably in the range from 1:20 to 20:1, more preferably in the range from 1:10 to 10:1, even more preferably in the range from 1:4 to 4:1, and especially in the range from 1:2 to 2:1. According to another embodiment, the weight ratio of component 1) to component 2) is generally in the range from 1000:1 to 1:1, often in the range from 100:1 to 1:1, frequently in the range from 50:1 to 1:1, preferably in the range from 20:1 to 1:1, more preferably in the range from 10:1 to 1:1, even more preferably in the range from 4:1 to 1:1, and especially in the range from 2:1 to 1:1. According to another embodiment, the weight ratio of component 1) to component 2) is generally in the range from 20,000:1 to 1:10, often in the range from 10,000:1 to 1:1, frequently in the range from 5,000:1 to 5:1, preferably in the range from 5,000:1 to 10:1, more preferably in the range from 2,000:1 to 30:1, even more preferably in the range from 2,000:1 to 100:1, and especially in the range from 1,000:1 to 100:1. According to another embodiment, the weight ratio of component 1) to component 2) is generally in the range from 1:1 to 1:1000, often in the range from 1:1 to 1:100, frequently in the range from 1:1 to 1:50, preferably in the range from 1:1 to 1:20, more preferably in the range from 1:1 to 1:10, even more preferably in the range from 1:1 to 1:4, and especially in the range from 1:1 to 1:2. According to another embodiment, the weight ratio of component 1) to component 2) is generally in the range from 10:1 to 1:20,000, often in the range from 1:1 to 1:10,000, frequently in the range from 1:5 to 1:5,000, preferably in the range from 1:10 to 1:5,000, more preferably in the range from 1:30 to 1:2,000, even more preferably in the range from 1:100 to 1:2,000, and especially in the range from 1:100 to 1:1,000.

[0467] In a ternary mixture, i.e. a composition comprising component 1) and component 2) and compound III (component 3), the weight ratio of component 1) to component 2) depends on the properties of the active substances used and is generally in the range from 1:100 to 100:1, frequently in the range from 1:50 to 50:1, preferably in the range from 1:20 to 20:1, more preferably in the range from 1:10 to 10:1, and especially in the range from 1:4 to 4:1, and the weight ratio of component 1) to component 3) is generally in the range from 1:100 to 100:1, frequently in the range from 1:50 to 50:1, preferably in the range from 1:20 to 20:1, more preferably in the range from 1:10 to 10:1, and especially in the range from 1:4 to 4:1. If desired, any additional active component is added to component 1) in a ratio from 20:1 to 1:20. These ratios are also suitable for mixtures applied by seed treatment.

[0468] When a mixture containing a microbial pest-killing agent is used for crop protection, the application rate ranges from 1×10 6 to 5×10 16 (or more) CFU / ha, preferably from 1×10 8 to 1×10 13 CFU / ha, and even more preferably from 1×10 9 to 5×10 15 CFU / ha, and especially from 1×10 12 to 5×10 14 CFU / ha. In the case of nematodes as microbial pest-killing agents (e.g., Steinernema carpocapsae), the application rate range is often from 1×10 5 to 1×10 12 (or more), preferably from 1×10 8 to 1×10 11 , more preferably from 5×10 8 to 1×10 10 individuals (e.g., in the form of eggs, larvae or any other living stage, preferably in the non-reproductive (infetive) larval stage) / ha.

[0469] When a mixture containing a microbial pest-killing agent is used for seed treatment, the application rate range is generally from 1×10 6 to 1×10 12 (or more) CFU / seed, preferably from 1×10 6 to 1×10 9 CFU / seed. In addition, the application rate range for seed treatment is generally from 1×10 7 to 1×10 14 (or more) CFU / 100 kg of seeds, preferably from 1×10 9 to 1×10 12 CFU / 100 kg of seeds.

[0470] Preferably, a mixture containing at least one active substance as component 2), the at least one active substance being selected from group A) in Q oComplex III inhibitors at the site, more preferably selected from compounds (A.1.1), (A.1.4), (A.1.8), (A.1.9), (A.1.10), (A.1.12), (A.1.13), (A.1.14), (A.1.17), (A.1.21), (A.1.25), (A.1.34) and (A.1.35); particularly selected from (A.1.1), (A.1.4), (A.1.8), (A.1.9), (A.1.13), (A.1.14), (A.1.17), (A.1.25), (A.1.34) and (A.1.35).

[0471] Also preferred is a mixture comprising at least one active substance as component 2), said at least one active substance being selected from the complex III inhibitors of group A) at Q i Complex III inhibitors at the site, more preferably selected from compounds (A.2.1), (A.2.3), (A.2.4) and (A.2.6); particularly selected from (A.2.3), (A.2.4) and (A.2.6).

[0472] Also preferred is a mixture comprising at least one active substance as component 2), said at least one active substance being selected from the complex II inhibitors of group A), more preferably selected from 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.3.37), (A.3.38) and (A.3.39); particularly 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).

[0473] Also preferred is a mixture comprising at least one active substance as component 2), said at least one active substance being selected from other respiratory inhibitors of group A), more preferably selected from compounds (A.4.5) and (A.4.11); in particular (A.4.11).

[0474] Also preferred is a mixture comprising at least one active substance as component 2), said at least one active substance being selected from C14-demethylase inhibitors of group B), more preferably selected from 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), (B.1.43), (B.1.46), (B.1.53), (B.1.54) and (B.1.55); particularly 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).

[0475] Also preferred is a mixture comprising at least one active substance as component 2), said at least one active substance being selected from δ14-reductase inhibitors of group B), more preferably selected from compounds (B.2.4), (B.2.5), (B.2.6) and (B.2.8); in particular (B.2.4).

[0476] Also preferred is a mixture comprising at least one active substance as component 2), said at least one active substance being selected from phenylamide and acylamino acid fungicides of group C), more preferably selected from compounds (C.1.1), (C.1.2), (C.1.4) and (C.1.5); particularly selected from (C.1.1) and (C.1.4).

[0477] Also preferred is a mixture comprising at least one active substance as component 2), said at least one active substance being selected from other nucleic acid synthesis inhibitors of group C), more preferably selected from compounds (C.2.6), (C.2.7) and (C.2.8).

[0478] Also preferred is a mixture comprising at least one active substance as component 2), said at least one active substance being 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); particularly selected from (D.1.2), (D.1.5) and (D.2.6).

[0479] Also preferred is a mixture comprising at least one active substance as component 2), said at least one active substance being selected from group E), more preferably selected from the compounds (E.1.1), (E.1.3), (E.2.2) and (E.2.3); particularly (E.1.3).

[0480] Also preferred is a mixture comprising at least one active substance as component 2), said at least one active substance being selected from group F), more preferably selected from the compounds (F.1.2), (F.1.4) and (F.1.5).

[0481] Also preferred is a mixture comprising at least one active substance as component 2), said at least one active substance being selected from group G), more preferably selected 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); particularly selected from (G.3.1), (G.5.1) and (G.5.3).

[0482] Also preferred is a mixture comprising at least one active substance as component 2), said at least one active substance being 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); particularly selected from (H.2.2), (H.2.5), (H.3.2), (H.4.9) and (H.4.10).

[0483] Also preferred is a mixture comprising at least one active substance as component 2), said at least one active substance being selected from group I), more preferably selected from the compounds (I.2.2) and (I.2.5).

[0484] Also preferred is a mixture comprising at least one active substance as component 2), said at least one active substance being 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); particularly (J.1.5).

[0485] Also preferably, a mixture comprising at least one active substance as component 2), which at least one active substance is selected from group K), more preferably selected from compounds (K.1.41), (K.1.42), (K.1.44), (K.1.47), (K.1.57), (K.1.58) and (K.1.59); particularly selected from (K.1.41), (K.1.44), (K.1.47), (K.1.57), (K.1.58) and (K.1.59).

[0486] The biopesticides from group L1) and / or L2) may also have insecticidal, acaricidal, molluscicidal, pheromonal, nematicidal, plant stress reducing, plant growth regulating, plant growth promoting and / or yield increasing activities. The biopesticides from group L3) and / or L4) may also have fungicidal, bactericidal, virucidal, plant defense activating, plant stress reducing, plant growth regulating, plant growth promoting and / or yield increasing activities. The biopesticides from group L5) may also have fungicidal, bactericidal, virucidal, plant defense activating, insecticidal, acaricidal, molluscicidal, pheromonal and / or nematicidal activities.

[0487] Microbial biopesticides, especially those from groups L1), L3) and L5), include not only isolated pure cultures of the corresponding microorganisms as defined herein, but also their cell-free extracts, their suspensions in whole broth cultures and media containing metabolites, or purified metabolites obtained from whole broth cultures of the microorganisms.

[0488] Many of these biopesticides are deposited under the accession numbers mentioned herein (the prefixes such as ATCC or DSM refer to the initials of the corresponding culture depositories, for details see, for example, http: / / www.wfcc.info / ccinfo / collection / by_acronym / ), are mentioned in the literature, are registered and / or are commercially available: the mixture of Aureobasidium pullulans DSM14940 and DSM 14941 was isolated in 1989 in Konstanz, Germany (e.g., blastospores, from ) of bio-ferm GmbH, Austria), Azospirillum brasilense Sp245 was initially isolated at least before 1980 in the wheat area of southern Brazil (Passo Fundo) (BR 11005; e.g., from Gramíneas), Azospirillum brasilense strains Ab-V5 and Ab-V6 (e.g., AzoMax from Novozymes BioAg Produtos papra Agricultura Ltda., Quartelúpolis, Brazil, or PlantSoil 331, 413 - 425, 2010), Bacillus amyloliquefaciens strain AP-188 (NRRL B-50615 and B-50331; US 8,445,255); Bacillus amyloliquefaciens subsp. plantarum strains, sometimes previously also referred to as Bacillus subtilis, recently classified together with Bacillus methylotrophicus and Bacillus velezensis as Bacillus velezensis (Int. J. Syst. Evol. Microbiol. [International Journal of Systematic and Evolutionary Microbiology] 66, 1212–1217, 2016); Bacillus amyloliquefaciens subsp. plantarum or Bacillus velezensis D747 isolated from the air in Kikugawa, Japan (US20130236522 A1; FERM BP-8234; e.g., Double Nickel TM 55WDG from Certis LLC, USA), Bacillus amyloliquefaciens subsp. plantarum or Bacillus velezensis FZB24 isolated from soil in Brandenburg, Germany (also known as SB3615; DSM 96-2; J. Plant Dis. Prot. [Journal of Plant Diseases and Protection] 105, 181 - 197, 1998; e.g., ) from Novozyme Biologicals, Inc., USA), Bacillus amyloliquefaciens subsp. plantarum or Bacillus velezensis FZB42 isolated from soil in Brandenburg, Germany (DSM 23117; J. Plant Dis. Prot. [Journal of Plant Diseases and Protection] 105, 181 - 197, 1998; e.g., 42) from AbiTEP GmbH, Germany), Bacillus amyloliquefaciens subsp. plantarum or Bacillus velezensis MBI600 (also known as 1430; NRRL B-50595; US2012 / 0149571A1) isolated from Vicia faba in Sutton Bonington, Nottinghamshire, UK at least before 1988; e.g., ) from BASF Corporation, USA), Bacillus amyloliquefaciens subsp. plantarum or Bacillus velezensis QST-713 (NRRL B-21661) isolated from a peach orchard in California, USA in 1995; e.g., MAX), Bacillus amyloliquefaciens subsp. plantarum or Bacillus velezensis TJ1000 (also known as 1BE; ATCC BAA-390; CA 2471555 A1; e.g., QuickRoots from TJ Technologies, Watertown, South Dakota, USA TM ); Bacillus firmus CNCM I-1582, a variant of the parental strain EIP-N1 isolated from soil in the Central Region of Israel (CNCM I-1556) (WO 2009 / 126473, US 6,406,690; e.g., from Bayer CropScience LP, USA ), Bacillus pumilus GHA 180 isolated from apple rhizosphere in Mexico (IDAC 260707-01; e.g., from Premier Horticulture, Quebec, Canada BX), Bacillus pumilus INR-7, also known as BU-F22 and BU-F33, isolated at least prior to 1993 from cucumber plants infected with Erwinia tracheiphila (NRRL B-50185, NRRL B-50153; US 8,445,255), Bacillus pumilus KFP9F isolated at least prior to 2008 from grass rhizosphere in South Africa (NRRL B-50754; WO 2014 / 029697; e.g., BAC-UP or FUSION-P from BASF Agricultural Specialities (Pty) Ltd., South Africa), Bacillus pumilus QST 2808 isolated in 1998 from soil collected in Pohnpei, Federated States of Micronesia (NRRL B-30087; e.g., from Bayer CropScience, USA or Plus), Bacillus simplex ABU 288 (NRRL B-50304; US 8,445,255), also known as UD 1022 or UD10-22, Bacillus subtilis FB17 was isolated from red beetroot in North America (ATCC PTA-11857; System. Appl. Microbiol. [System and Applied Microbiology] 27, 372-379, 2004; US2010 / 0260735; WO 2011 / 109395); Bacillus thuringiensis subsp. aizawai ABTS-1857 was isolated in 1987 from soil taken from a lawn in Ephraim, Wisconsin, USA (also known as ABG-6346; ATCC SD-1372; e.g., from BioFa AG, Münsingen, Germany ), Bacillus thuringiensis subsp. kurstaki ABTS-351 is equivalent to HD-1 isolated in 1967 from diseased black larvae of the cotton bollworm, Helicoverpa armigera, in Brownsville, Texas, USA (ATCC SD-1275; e.g., from Valent BioSciences, Illinois, USA DF), Bacillus thuringiensis subsp. kurstaki SB4 was isolated from the cadavers of larvae of the African sugarcane borer, Eldana saccharina (NRRL B-50753; e.g., from BASF Agricultural Specialities (Pty) Ltd., South Africa ), Bacillus thuringiensis subsp. tenebrionis NB-176-1, a mutant of strain NB-125, a wild-type strain isolated from dead pupae of the beetle Tenebrio molitor in 1982 (DSM 5480; EP 585215B1; e.g., from Valent BioSciences, Switzerland ), Beauveria bassiana GHA (ATCC 74250; e.g., from Laverlam Int. Corp., USA 22WGP), Beauveria bassiana JW-1 (ATCC74040; e.g., from CBC (Europe) S.r.l., Italy ), Beauveria bassiana PPRI 5339 was isolated from larvae of the tortoise beetle Conchyloctenia punctata (NRRL 50757; e.g., from BASF Agricultural Specialities (Pty) Ltd., South Africa ),The Bradyrhizobium elkanii strain SEMIA 5019 (also known as 29W) was isolated in Rio de Janeiro, Brazil and SEMIA 587 was isolated in 1967 in the State of Rio Grande do Sul, from an area previously inoculated with North American isolates and has been used for commercial inoculants since 1968 (Appl. Environ. Microbiol. [Applied and Environmental Microbiology] 73(8), 2635, 2007; e.g., GELFIX 5 from BASF Agricultural Specialties Ltd., Brazil), Bradyrhizobium japonicum 532c was isolated from a field in Wisconsin, USA (Nitragin 61A152; Can. J. Plant Sci. [Canadian Journal of Plant Sciences] 70, 661 - 666, 1990; e.g., (Super), Bradyrhizobium japonicum E-109 variant of strain USDA 138 (INTA E109, SEMIA 5085; Eur. J. Soil Biol. [European Journal of Soil Biology] 45, 28 - 35, 2009; Biol. Fertil. Soils [Biology and Fertility of Soils] 47, 81–89, 2011); Bradyrhizobium japonicum strains known to be deposited at SEMIA by Appl. Environ. Microbiol. [Applied and Environmental Microbiology] 73(8), 2635, 2007: Bradyrhizobium japonicum SEMIA 5079 was isolated from soil by Embrapa-Cerrados in the Cerrados region of Brazil and has been used for commercial inoculants since 1992 (CPAC 15; e.g., GELFIX 5 or ADHERE60 from BASF Agricultural Specialties Ltd. of Brazil), Bradyrhizobium japonicum SEMIA 5080 was obtained under laboratory conditions by Embrapa-Cerrados in Brazil and has been used for commercial inoculants since 1992 and is a natural variant of SEMIA 586 (CB1809) originally isolated in the United States (CPAC7; e.g., GELFIX 5 or ADHERE 60 from BASF Agricultural Specialties Ltd. of Brazil); Burkholderia species A396 was isolated from soil in Nikko, Japan in 2008 (NRRLB-50319; WO 2013 / 032693; Marrone Bio Innovations, Inc. of the United States), Coniothyrium minitans CON / M / 91-08 was isolated from Brassica napus (WO 1996 / 021358; DSM 9660; e.g., WG, WG), hypersensitive protein (α-β) protein (Science [Science] 257, 85 - 88, 1992; e.g., Messenger from Plant Health Care plc of the United Kingdom TM or HARP-N-Tek), Helicoverpa armigera nucleopolyhedrovirus (HearNPV) (J. Invertebrate Pathol [Journal of Invertebrate Pathology]. 107, 112 - 126, 2011; e.g., from Koppert of Brazil From AgBiTech Pty Ltd., Queensland, Australia Max), Helicoverpa zea single nucleocapsid nucleopolyhedrovirus (HzSNPV) (e.g., from Certis LLC, USA ), Helicoverpa zea nucleopolyhedrovirus ABA-NPV-U (e.g., from AgBiTech Pty Ltd., Queensland, Australia ), Heterorhabditis bacteriophora (e.g., from BASF Agricultural Specialities Limited, UK G), Isaria fumosorosea Apopka-97 isolated from mealybugs on Gynura aurantiaca in Apopka, Florida, USA (ATCC 20874; Biocontrol Science Technol [Biological Control Science and Technology]. 22(7), 747-761, 2012; e.g., PFR-97TM from Certis LLC, USA or ), Metarhizium anisopliae var. anisopliae F52, also known as 275 or V275, isolated from Cydia pomonella in Austria (DSM 3884, ATCC 90448; e.g., Novozymes Biologicals BioAg Group, Canada), Metschnikowia fructicola 277 isolated from grapes in the central region of Israel (US 6,994,849; NRRL Y-30752; e.g., previously from Agrogreen, Israel ), Paecilomyces lilacinus 251 isolated from infected nematode eggs in the Philippines (AGAL 89 / 030550; WO 1991 / 02051; Crop Protection [Crop Protection] 27, 352-361, 2008; e.g., from Bayer CropScience AG, Germany and from Certis, USA ) The Paenibacillus alvei NAS6G6 was isolated from the rhizosphere of grass roots in South Africa at least before 2008 (WO 2014 / 029697; NRRL B-50755; for example, BAC-UP from BASF Agricultural Specialities (Pty) Ltd. in South Africa), Paenibacillus strains isolated from soil samples in various European regions including Germany: Paenibacillus adhaerens Lu17015 (WO 2016 / 020371; DSM 26971), Paenibacillus polymyxa subsp. plantarum Lu16774 (WO 2016 / 020371; DSM 26969), Paenibacillus polymyxa subsp. plantarum strain Lu17007 (WO 2016 / 020371; DSM 26970); Pasteuria nishizawae Pn1 was isolated from a soybean field in Illinois, USA in the mid-2000s (ATCC SD-5833; Federal Register 76(22), 5808, February 2, 2011; for example, Clariva from Syngenta Crop Protection, LLC in the USA TM PN), Penicillium bilaiae (also known as P. bilaii) strains ATCC 18309 (= ATCC 74319), ATCC 20851, and / or ATCC 22348 (= ATCC 74318) were initially isolated from soil in Alberta, Canada (Fertilizer Res. 39, 97-103, 1994; Can. J. Plant Sci. 78(1), 91-102, 1998; US 5,026,417, WO 1995 / 017806; for example, Jump from Novozymes Biologicals BioAg Group in Canada ) The extract of Reynoutria japonica Houtt. (EP 0307510 B1; for example, SC from Marrone BioInnovations, Davis, CA, USA or ) from BioFa AG in Germany), Steinernema carpocapsae (for example, ) from BASF Agricultural Specialities Limited in the UK, Steinernema feltiae (for example, from BASF Agricultural Specialities Limited, UK ), Streptomyces microflavus NRRL B-50550 (WO2014 / 124369; Bayer CropScience AG, Germany), Trichoderma pseudokoningii JM41R isolated in South Africa (NRRL 50759; also known as Trichoderma asperellum; e.g., from BASF Agricultural Specialities (Pty) Ltd., South Africa ), Trichoderma harzianum T-22 also known as KRL-AG2 (ATCC 20847; BioControl 57, 687-696, 2012; e.g., from BioWorks Inc., USA or SabrEx from Advanced Biological Marketing Inc., Van Wert, Ohio, USA TM ).

[0489] According to another embodiment of the mixture, at least one pesticidal agent II is selected from groups L1) to L5):

[0490] L1) Microbial pest control agents with fungicidal, bactericidal, virucidal and / or plant defense activator activities: Aureobasidium pullulans DSM 14940 and DSM 14941 (L1.1), Bacillus amyloliquefaciens AP-188 (L.1.2), Bacillus amyloliquefaciens subsp. plantarum D747 (L.1.3), Bacillus amyloliquefaciens subsp. plantarum FZB24 (L.1.4), Bacillus amyloliquefaciens subsp. plantarum FZB42 (L.1.5), Bacillus amyloliquefaciens subsp. plantarum MBI600 (L.1.6), Bacillus amyloliquefaciens subsp. QST-713 (L.1.7), Bacillus amyloliquefaciens subsp. TJ1000 (L.1.8), Bacillus pumilus GB34 (L.1.9), Bacillus pumilus GHA 180 (L.1.10), Bacillus pumilus INR-7 (L.1.11), Bacillus pumilus KFP9F (L.1.12), Bacillus pumilus QST 2808 (L.1.13), Bacillus simplex ABU 288 (L.1.14), Bacillus subtilis FB17 (L.1.15), Coniothyrium minitans CON / M / 91-08 (L.1.16), Metschnikowia fructicola NRRL Y-30752 (L.1.17), Paenibacillus alvei NAS6G6 (L.1.18), Paraburkholderia epiphytica Lu17015 (L.1.25), Paenibacillus polymyxa subsp. plantarum Lu16774 (L.1.26), Paenibacillus polymyxa subsp. strain Lu17007 (L.1.27), Penicillium bilaiae ATCC 22348 (L.1.19), Penicillium bilaiae ATCC 20851 (L.1.20), Penicillium bilaiae ATCC 18309 (L.1.21), Streptomyces microflavus NRRLB-50550 (L.1.22), Trichoderma asperellum JM41R (L.1.23), Trichoderma harzianum T-22 (L.1.24);

[0491] L2) Biochemical pest control agents with fungicidal, bactericidal, virucidal and / or plant defense activator activities: harpins (L.2.1), Reynoutria japonica extract (L.2.2);

[0492] L3) Microbial pesticides with insecticidal, acaricidal, molluscicidal and / or nematicidal activity: Bacillus firmus I-1582 (L.3.1); Bacillus thuringiensis subsp. aizawai ABTS-1857 (L.3.2), Bacillus thuringiensis subsp. kurstaki ABTS-351 (L.3.3), Bacillus thuringiensis subsp. kurstaki SB4 (L.3.4), Bacillus thuringiensis subsp. tenebrionis NB-176-1 (L.3.5), Beauveria bassiana GHA (L.3.6), Beauveria bassiana JW-1 (L.3.7), Beauveria bassiana PPRI 5339 (L.3.8), Burkholderia species A396 (L.3.9), Helicoverpa armigera nucleopolyhedrovirus (HearNPV) (L.3.10), Helicoverpa zea nucleopolyhedrovirus (HzNPV) ABA-NPV-U (L.3.11), Helicoverpa zea single nucleocapsid 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), Steinernema feltiae (L.3.19);

[0493] L4) Biochemical pesticides with insecticidal, acaricidal, molluscicidal, pheromonal and / or nematicidal activity: cis-jasmone (L.4.1), methyl jasmonate (L.4.2), Quillaja saponaria extract (L.4.3);

[0494] L5) Microbial pesticides with plant stress reduction, plant growth regulator, plant growth promotion and / or yield increase activity: Azospirillum brasilense Ab-V5 and Ab-V6 (L.5.1), Azospirillum brasilense Sp245 (L.5.2), Bradyrhizobium elkanii SEMIA 587 (L.5.3), Bradyrhizobium elkanii SEMIA 5019 (L.5.4), Bradyrhizobium japonicum 532c (L.5.5), Bradyrhizobium japonicum E-109 (L.5.6), Bradyrhizobium japonicum SEMIA 5079 (L.5.7), Bradyrhizobium japonicum SEMIA 5080 (L.5.8).

[0495] Furthermore, the present invention relates to agrochemical compositions which comprise a mixture of the following: 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 (if desired) at least one suitable adjuvant.

[0496] Furthermore, the present invention relates to agrochemical compositions which comprise a mixture of the following: 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 L3) and L4) as described above, and (if desired) at least one suitable adjuvant.

[0497] Also preferred are mixtures which comprise as pesticidal agent II (component 2) a biopesticide selected from groups L1), L3) and L5), preferably selected from the strains designated above as (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 selected from (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), (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 treating propagation material, i.e. for seed treatment purposes, and are equally suitable for soil treatment. These seed treatment mixtures are particularly suitable for crops such as cereals, maize and leguminous plants such as soybeans.

[0498] Also preferred are mixtures comprising a biopesticide as pesticidal agent II (component 2), which biopesticide is selected from group L1), L3) and L5), preferably selected from the strains designated above as (L1.1), (L1.2), (L1.3), (L1.6), (L1.7), (L1.9), (L1.11), (L1.12), (L1.13), (L1.14), (L1.15), (L1.17), (L1.18), (L1.22), (L1.23), (L1.24), (L1.25), (L1.26), (L1.27), (L2.2); (L3.2), (L3.3), (L3.4), (L3.5), (L3.6), (L3.7), (L3.8), (L3.10), (L3.11), (L3.12), (L3.13), (L3.14), (L3.15), (L3.18), (L3.19); (L4.2), even more preferably selected from (L1.2), (L1.7), (L1.11), (L1.13), (L1.14), (L1.15), (L1.18), (L1.23), (L3.3), (L3.4), (L3.6), (L3.7), (L3.8), (L3.10), (L3.11), (L3.12), (L3.15) and (L4.2). These mixtures are particularly suitable for treatment of the foliage of cultivated plants, preferably vegetables, fruits, vines, cereals, maize and leguminous crops such as soybeans.

[0499] Compositions comprising mixtures of active ingredients can be prepared by customary means, for example by the means given for the compositions of compound I.

[0500] When living microorganisms such as pesticidal agents II from group L1), L3) and L5) form part of the composition, such compositions can be prepared by customary means (e.g. H.D. Burges: Formulation of Microbial Biopesticides, Springer, 1998; WO 2008 / 002371, US 6,955,912, US 5,422,107).

[0501] I. Synthesis example

[0502] Example 1: 5-(6-(difluoromethyl)-5-methylpyridin-3-yl)-4-methyl-4,5-dihydro-2H-spiro[benzo[f] [1,4]oxazepine -3,1'-cyclopropane]

[0503] Step 1: Preparation of spiro[chroman-3,1'-cyclopropane]-4-one oxime

[0504]

[0505] Hydroxylamine hydrochloride (2.4 g, 34.56 mmol) was added to a solution of spiro[chroman-3,1'-cyclopropane]-4-one (3.0 g, 17.28 mmol) in pyridine (20 mL, 247.79 mmol), and the reaction mixture was stirred at 85 °C for 18 h. The reaction mixture was cooled to room temperature and poured into water (100 mL). Then, the solution was extracted with EtOAc and dried over Na2SO4. The solvent was removed in vacuo to give spiro[chroman-3,1'-cyclopropane]-4-one oxime (3.3 g, 99%) as a clear oil. The title compound was used directly without further purification.

[0506] Z-isomer

[0507] 1 H NMR (400 MHz, CDCl3) δ [ppm] = 9.13 (br s, 1H), 8.82 (dd, J = 8.2, 1.7 Hz, 1H), 7.82 (dd, J = 7.9, 1.7 Hz, 1H), 7.39 - 7.19 (m, 1H), 7.05 - 6.86 (m, 1H), 3.79 (s, 2H), 2.23 - 2.13 (m, 2H), 0.90 - 0.84 (m, 2H).

[0508] E-isomer

[0509] 1 H NMR (400 MHz, CDCl3) δ [ppm] = 9.55 (s, 1H), 8.67–8.61 (m, 1H), 7.70 (m, 1H), 7.39 - 7.19 (m, 1H), 7.05 - 6.86 (m, 1H), 4.04 (s, 2H), 1.26 - 1.17 (m, 2H), 0.82 - 0.76 (m, 2H).

[0510] Step 2: Preparation of 2H-spiro[benzo[f][1,4]oxazepine -3,1'-cyclopropane]-5(4H)-one

[0511]

[0512] At a temperature below 20 °C, spiro[chromane-3,1'-cyclopropane]-4-one oxime (3.2 g, 17.18 mmol) was added to thionyl chloride (4.9 g, 41.13 mmol), and the reaction mixture was stirred at room temperature for 17 h. After removing thionyl chloride in vacuo, the residue was poured into 1,4-dioxane (50 ml) and water (25 ml), and stirred at 80 °C for 1 h. After removing 1,4-dioxane in vacuo, the residue was extracted with EtOAc (100 mL) and dried over Na2CO3. The solvent was removed in vacuo to give 2H-spiro[benzo[f][1,4]oxazepine -3,1'-cyclopropane]-5(4H)-one (1.8 g, 56%) as a beige solid. The title compound was used directly without further purification.

[0513] 1 1H NMR (400 MHz, CDCl3) δ [ppm] = 7.88 (dd, J = 7.8, 1.8 Hz, 1H), 7.42 (ddd, J = 8.2, 7.2, 1.8 Hz, 1H), 7.24 (br s, 1H), 7.13 (ddd, J = 7.8, 7.2, 1.2 Hz, 1H), 7.02 (dd, J = 8.2, 1.2 Hz, 1H), 4.24 (s, 2H), 0.93 - 0.86 (m, 2H), 0.83 - 0.76 (m, 2H).

[0514] Step 3: Preparation of 5-chloro-2H-spiro[benzo[f][1,4]oxazepine -3,1'-cyclopropane

[0515]

[0516] A mixture of 2H-spiro[benzo[f][1,4]oxazepine -3,1'-cyclopropane]-5(4H)-one (300 mg, 1.59 mmol) and phosphoryl chloride (1.5 mL, 16.09 mmol) was stirred at 110 °C for 1 h. After cooling, the reaction solution was concentrated in vacuo, diluted with dichloromethane (30 mL), washed twice with a saturated aqueous solution of Na2CO3, and dried over Na2SO4. The solvent was removed in vacuo to give 5-chloro-2H-spiro[benzo[f][1,4]oxazepine -3,1'-cyclopropane (310 mg, 99%) as a clear oil. The title compound was used directly without further purification.

[0517] Step 4: 5-(6-(Difluoromethyl)-5-methylpyridin-3-yl)-2H-spiro[benzo[f][1,4]oxazepine -3,1'-spirocyclopropane]

[0518]

[0519] (6-(Difluoromethyl)-5-methylpyridin-3-yl)boronic acid (290 mg, 1.04 mmol), potassium carbonate (430 mg, 2.08 mmol) and dichlorobis(triphenylphosphine)palladium(II) (105 mg, 0.15 mmol) were added to a solution of 5-chloro-2H-spiro[benzo[f][1,4]oxazepine -3,1'-spirocyclopropane] (310 mg, 1.49 mmol) in DME (6 mL) and water (2 mL), and the mixture was stirred at 100 °C for 2 h under an argon atmosphere. After cooling, the reaction mixture was concentrated in vacuo. The crude product was purified by high performance liquid chromatography on silica RP-18 using MeCN / water as the eluent to give 5-(6-(difluoromethyl)-5-methylpyridin-3-yl)-2H-spiro[benzo[f][1,4]oxazepine -3,1'-spirocyclopropane] (1.5 g) as a pale brown oil.

[0520] 1 1H NMR (400 MHz, CDCl3) δ [ppm] = 8.51 (d, J = 2.0 Hz, 1H), 7.75 (d, J = 2.0 Hz, 1H), 7.39 (ddd, J = 8.5, 6.8, 2.0 Hz, 1H), 7.11 (dd, J = 8.2, 1.2 Hz, 1H), 7.07 - 6.97 (m, 2H), 6.72 (t, J = 54.5 Hz, 1H), 4.37 (s, 2H), 2.53 (t, 3H), 1.14 - 1.06 (m, 2H), 1.04 - 0.93 (m, 2H).

[0521] Step 5: Preparation of 5-(6-(difluoromethyl)-5-methylpyridin-3-yl)-4,5-dihydro-2H-spiro[benzo[f][1,4]oxazepine -3,1'-spirocyclopropane]

[0522]

[0523] 5-(6-(Difluoromethyl)-5-methylpyridin-3-yl)-2H-spiro[benzo[f][1,4]oxazepine A solution of -3,1'-cyclopropane](256 mg, 0.81 mmol) in MeOH (6 mL) was cooled to 0 °C. Then, under N2, NaBH4 (185 mg, 4.89 mmol) was added in two portions, and the reaction mixture was stirred at 0 °C to 20 °C under N2 for 4 h. TLC (PE:MTBE = 4:1) showed completion of the reaction. The reaction mixture was quenched with water (0.5 mL), concentrated and purified by column (PE:MTBE = 4:1) to give 5-(6-(difluoromethyl)-5-methylpyridin-3-yl)-4,5-dihydro-2H-spiro[benzo[f][1,4]oxazepine

[0524] 1 as a white solid (182 mg, 67%).

[0525] Step 6: Preparation of 5-(6-(difluoromethyl)-5-methylpyridin-3-yl)-4-methyl-4,5-dihydro-2H-spiro[benzo[f][1,4]oxazepine -3,1'-cyclopropane

[0526]

[0527] At room temperature, to 5-(6-(difluoromethyl)-5-methylpyridin-3-yl)-4,5-dihydro-2H-spiro[benzo[f][1,4]oxazepine A solution of [[1,3']bicyclopropane](107 mg, 0.34 mmol) in MeCN (2 mL) was added with aqueous formaldehyde solution (275 mg, 3.39 mmol), sodium cyanoborohydride (64 mg, 1.01 mmol) and acetic acid (0.1 mL, 1.75 mmol). The mixture was stirred at room temperature for 3 h. TLC (PE:MTBE = 4:1) showed the reaction was complete. The reaction mixture was quenched with 1 M aqueous NaOH solution (1 mL), extracted twice with MTBE (20 mL), dried over Na2SO4, filtered and concentrated. The crude mixture was purified by column (PE:MTBE = 4:1) to give 5-(6-(difluoromethyl)-5-methylpyridin-3-yl)-4-methyl-4,5-dihydro-2H-spiro[benzo[f][1,4]oxazepine -3,1'-bicyclopropane](75 mg, 64%).

[0528] 1 1H NMR (400 MHz, CDCl3) δ [ppm] = 8.42 (s, 1H), 7.54 (s, 1H), 7.33 - 7.26 (m, 2H), 7.11 (dd, J = 8.0, 1.3 Hz, 1H), 7.02 (td, J = 7.5, 1.3 Hz, 1H), 6.75 (d, J = 7.5 Hz, 1H), 6.71 (t, J = 54.6 Hz, 1H), 5.35 (s, 1H), 4.35 (d, J = 12.2 Hz, 1H), 3.53 (d, J = 12.2 Hz, 1H), 2.49 (s, 2H), 2.39 (s, 3H), 0.76 - 0.54 (m, 1H), 0.51 - 0.41 (m, 1H), 0.40 - 0.30 (m, 2H).

[0529] The compounds listed in Table I were prepared in a similar manner.

[0530] Table I: Compounds Ex-1 to Ex-12 having formula I, where R 2 、R 3 、R 5 、R 6 、R 7 、R 8 、R 9 and the meanings of Xn are defined as in each row.

[0531] *HPLC: High Performance Liquid Chromatography; HPLC-column Kinetex XB C18 1,7 μ (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 from 0.8 to 1.0 ml / min in 1.5 min);

[0532] *LCMS: Liquid Chromatography-Mass Spectrometry; Shimadzu Nexera LC-30LCMS-2020 (ESI+), using HPLC-column Kinetex XB C18 1,7 μ (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 from 0.8 to 1.0 ml / min in 1.5 min); R t : Retention time in minutes.

[0533]

[0534] #imgpt179#

[0535] II. Biological example

[0536] Microtest

[0537] The active compound was formulated separately as a stock solution at a concentration of 10,000 ppm in dimethyl sulfoxide.

[0538] Example 1 - Activity against Botrytis cinerea in microtiter plate tests

[0539] The stock solutions were mixed proportionally, pipetted onto a microtiter plate (MTP) and diluted with water to the specified concentration. Then a spore suspension of Botrytis cinerea in a biological malt aqueous solution or a yeast-bacterial peptone-sodium acetate solution was added. The plates were placed in a water vapor-saturated chamber at a temperature of 18 °C. The MTP was measured at 405 nm 7 days after inoculation using an absorption photometer.

[0540] In this test, samples treated with 31 ppm of the active substances from Examples Ex-1, Ex-2, Ex-6 and Ex-7 showed a pathogen growth rate of 23%.

[0541] Example 2 - Activity against Botrytis cinerea in microtiter plate tests

[0542] The active compound was formulated separately as a stock solution at a concentration of 10,000 ppm in dimethyl sulfoxide. The stock solutions were mixed proportionally, pipetted onto a microtiter plate (MTP) and diluted with water to the specified concentration. Then a spore suspension of Botrytis cinerea in a biological malt aqueous solution or a yeast-bacterial peptone-sodium acetate solution was added.

[0543] In this test, samples treated with 31 ppm of the active substance from Examples Ex-1, Ex-2, Ex-4, Ex-5, Ex-6, Ex-7 and Ex-8 showed a pathogen growth rate of up to 1%.

[0544] Example 3 - Activity against Corynespora cassiicola in a microtiter plate test

[0545] The active compound was separately formulated as a stock solution at a concentration of 10,000 ppm in dimethyl sulfoxide. The stock solutions were mixed proportionally, pipetted onto a microtiter plate (MTP) and diluted with water to the specified concentration. Then, a spore suspension of Corynespora cassiicola isolate in DOB medium (pH 7) was added.

[0546] In this test, samples treated with 31 ppm of the active substance from Examples Ex-1, Ex-6 and Ex-7 showed a pathogen growth rate of up to 15%.

[0547] Example 4 - Activity against Fusarium culmorum in a microtiter plate test

[0548] The stock solutions were mixed proportionally, pipetted onto a microtiter plate (MTP) and diluted with water to the specified concentration. Then, a spore suspension of Fusarium culmorum in a biological malt aqueous solution or yeast - bacteriological peptone - glycerol or DOB solution was added. The plates were placed in a water - vapor - saturated chamber at a temperature of 18 °C. The MTP was measured at 405 nm 7 days after inoculation using an absorption photometer.

[0549] In this test, samples treated with 31 ppm of the active substance from Example Ex-1 showed a pathogen growth rate of 1%.

[0550] Greenhouse

[0551] The compound was dissolved in a mixture of acetone and / or dimethyl sulfoxide and the ethoxylated alkylphenol - based wetting agent / emulsifier Wettol in a solvent - emulsifier ratio (by volume) of 99:1 to obtain a total volume of 5 ml. Subsequently, water was added to a total volume of 100 ml.

[0552] This stock solution was then diluted with the solvent - emulsifier - water mixture to the final concentrations given in the table below.

[0553] Example 5 - Preventive fungicidal control of Botrytis cinerea on green pepper leaves

[0554] The green pepper seedlings are grown in pots until they reach the 4 - 5 leaf stage. These plants are sprayed with the aforementioned spray solution until runoff, which contains the active ingredient or mixture at the concentrations mentioned in the following table. The next day, the plants are inoculated with a biomaqueous solution or DOB solution containing a Botrytis cinerea spore suspension. Then the plants are immediately transferred to a humid chamber. After 5 days at 22°C to 24°C and saturated relative humidity, the degree of fungal infestation on the leaves is visually evaluated as the % diseased leaf area.

[0555] In this test, samples treated with 250 ppm of the active substances from Examples Ex - 1, Ex - 2, Ex - 4, Ex - 5, Ex - 6, Ex - 7, and Ex - 8 showed a pathogen growth rate of up to at most 11%, while 90% of the untreated plants were infected.

[0556] Example 6 - Long - term control of Botrytis cinerea on green pepper leaves

[0557] The green pepper seedlings are grown in pots until they reach the 4 - 5 leaf stage. These plants are sprayed with the aforementioned spray solution until runoff, which contains the active ingredient or mixture at the concentrations mentioned in the following table. Then, the plants are cultivated in a greenhouse for 7 days and then inoculated with a biomaqueous solution or DOB solution containing a Botrytis cinerea spore suspension. Then the plants are immediately transferred to a humid chamber. After 5 days at 22°C to 24°C and saturated relative humidity, the degree of fungal infestation on the leaves is visually evaluated as the % diseased leaf area.

[0558] In this test, samples treated with 125 ppm of the active substances from Examples Ex - 2, Ex - 4, Ex - 6, Ex - 7, and Ex - 8 showed a pathogen growth rate of up to at most 15%, while 90% of the untreated plants were infected.

[0559] Example 7 - Preventive fungicidal control of white mold on soybeans caused by Sclerotinia sclerotiorum

[0560] Soybean seedlings are planted in pots. These plants are sprayed with the aforementioned spray solution until runoff, which contains the active ingredient or its mixture at the concentrations mentioned in the following table. The plants can be air - dried. The next day, 25 μl of 2.5% methylcellulose is used to fix the applied rape petals on leaves 1 and 2. 25 μl of a Sclerotinia sclerotiorum spore suspension is pipetted onto each fixed rape petal. After 14 days at 20°C and 60% relative humidity, the degree of fungal infestation on the leaves is visually evaluated as the % diseased leaf area.

[0561] In this test, samples treated with 250 ppm of the active substances from Examples Ex - 4 and Ex - 7 showed a pathogen growth rate of up to at most 14%, while 100% of the untreated plants were infected.

[0562] Example 8 - Preventive fungicidal control of Sclerotinia white mould on oilseed rape

[0563] The oilseed rape was grown in pots up to the 13 - 14 leaf stage. These plants were sprayed to run-off with the aforementioned spray solution which contained the active ingredient or its mixtures at the concentrations mentioned in the table below. The plants could be air-dried. The next day, 25 μl of 2.5% methyl cellulose was used to fix the applied oilseed rape petals on leaves 1 and 2. 25 μl of a Sclerotinia spore suspension was pipetted onto each fixed oilseed rape petal. After 14 days at 20 °C and 60% relative humidity, the degree of fungal infestation on the leaves was visually evaluated as % diseased leaf area.

[0564] In this test, the samples treated with 100 g / ha of the active substance from Example Ex-7 showed a pathogen growth rate of up to at most 1%, while the untreated plants were 100% infected.

Claims

1. A compound of formula I or its N-oxide, tautomer, stereoisomer or agriculturally acceptable salt wherein R 1 independently selected from H, halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl in each case; R 2 independently selected in each case from halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, O-C1-C6-alkyl, O-C2-C6-alkenyl, O-C2-C6-alkynyl, C3-C6-cycloalkyl, S-C1-C6-alkyl, S-C2-C6-alkenyl, S-C2-C6-alkynyl; R 3 independently selected in each case from halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, O-C1-C6-alkyl, O-C2-C6-alkenyl, O-C2-C6-alkynyl, C3-C6-cycloalkyl, S-C1-C6-alkyl, S-C2-C6-alkenyl, S-C2-C6-alkynyl; and R 4 independently selected from H, halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl in each case; R 5 independently selected in each case from hydrogen, halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, benzyl, a five- or six-membered heteroaryl or a five- or six-membered CH2-heteroaryl; where the heteroaryl contains one, two or three heteroatoms selected from N, O and S; and where these aliphatic or aromatic groups are unsubstituted or carry 1, 2 or 3 substituents R 5a ; where Each R 5a independently is halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl or O-C1-C6-alkyl; R 6 independently selected in each case from hydrogen, halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, benzyl, a five- or six-membered heteroaryl or a five- or six-membered CH2-heteroaryl; where the heteroaryl contains one, two or three heteroatoms selected from N, O and S; and where these aliphatic or aromatic groups are unsubstituted or carry 1, 2 or 3 substituents R 6a ; where Each R 6a independently is halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl or O-C1-C6-alkyl; or R 5 and R 6 together form an oxo group (=O); or a thio group (=S); or R 5 and R 6 together with the carbon atom to which they are bonded form a 3-, 4-, 5- or 6-membered saturated carbon ring or a 3-, 4-, 5- or 6-membered saturated heterocyclic ring containing 1, 2 or 3 heteroatoms selected from O and S as ring members; wherein the carbon ring or heterocyclic ring is unsubstituted or bears 1, 2 or 3 substituents R 56 wherein Each R 56 independently is halogen, C1-C6-alkyl or C1-C6-haloalkyl; R 7 independently in each case selected from hydrogen, halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, benzyl, a five- or six-membered heteroaryl or a five- or six-membered CH2-heteroaryl; where the heteroaryl contains one, two or three heteroatoms selected from N, O and S; and where these aliphatic or aromatic groups are unsubstituted or carry 1, 2 or 3 substituents R 7a ; where Each R 7a independently is halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl or O-C1-C6-alkyl; R 8 independently selected in each case from hydrogen, halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, benzyl, a five- or six-membered heteroaryl or a five- or six-membered CH2-heteroaryl; where the heteroaryl contains one, two or three heteroatoms selected from N, O and S; and where these aliphatic or aromatic groups are unsubstituted or carry 1, 2 or 3 substituents R 8a ; where Each R 8a independently is halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl or O-C1-C6-alkyl; or R 7 and R 8 together form an oxo group (=O) or a thio group (=S); or R 7 and R 8 together with the carbon atom to which they are bonded form a 3-, 4-, 5- or 6-membered saturated carbon ring or a 3-, 4-, 5- or 6-membered saturated heterocyclic ring containing 1, 2 or 3 heteroatoms selected from O and S as ring members; R 9 independently selected in each case from H, 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)-N(H)C1-C4-alkyl, -C(=O)-N(C1-C4-alkyl)2, C1-C6-alkyl, C1-C6-alkoxy, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, -S(=O)2-R 9a , a five- or six-membered heteroaryl, aryl or benzyl; wherein the heteroaryl contains 1, 2 or 3 heteroatoms selected from N, O and S as ring members; wherein the benzene ring in the aryl and benzyl is unsubstituted or bears 1, 2, 3, 4 or 5 substituents selected from the group consisting of: CN, halogen, OH, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy and C1-C4-haloalkoxy; wherein the benzene ring in the benzyl is unsubstituted or bears 1, 2 or 3 substituents selected from the group consisting of: CN and halogen; wherein R 9a is a C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl or benzyl, where the benzene ring in the last two mentioned groups is unsubstituted or carries 1, 2 or 3 substituents each independently selected from the group consisting of: halogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl and C2-C6-haloalkynyl; X is independently selected in each case from halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-alkoxy or C1-C6-haloalkoxy, phenyl, benzyl, phenoxy, benzyloxy, C1-C6-thioalkyl; n is 0, 1, 2 or 3, provided that R 5 、R 6 、R 7 、R 8 They cannot all be H.

2. The compound according to claim 1, wherein, Y is CR 1 and R 1 is H.

3. The compound according to any one of claims 1 to 2, wherein, R 2 is a C1-C6-alkyl group.

4. The compound according to any one of claims 1 to 3, wherein R 2 is CH3.

5. The compound according to any one of claims 1 to 4, wherein R 3 selected from C1-C6-alkyl, C1-C6-haloalkyl.

6. The compound according to any one of claims 1 to 5, wherein R 3 is CH3 or CHF2.

7. The compound according to any one of claims 1 to 6, wherein R 4 is H.

8. The compound according to any one of claims 1 to 7, wherein R 5 and R 6 is H or a C1-C6-alkyl group.

9. The compound according to any one of claims 1 to 8, wherein, R 5 and R 6 together with the C atom to which they are bonded form a C3-C6-cycloalkyl or a (=O) group.

10. The compound according to any one of claims 1 to 9, wherein, R 7 and R 8 is H or a C1-C6-alkyl group.

11. The compound according to any one of claims 1 to 10, wherein, R 6 and R 7 together with the carbon atom to which they are bonded form a (=O) group.

12. A composition comprising a compound of formula I as defined in any one of claims 1 to 11, its N-oxide or an agriculturally acceptable salt thereof.

13. A method for combating phytopathogenic fungi, which method comprises treating the fungi or the material, plant, soil or seed to be protected against 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. A seed coated with from 0.1 to 10 kg / 100 kg of seed of at least one compound of formula I as defined in any one of claims 1 to 11 or an agriculturally acceptable salt thereof, or a composition as defined in any one of claims 12.

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