Substituted benzodiazepines as fungicides

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 benzodiazepines as fungicides compounds, their N-oxides and salts, and their use. The invention also relates to compositions comprising at least one compound I, methods for combating phytopathogenic fungi, and seeds coated with at least one compound of formula I.

[0002] WO 2011037128 discloses some benzodiazepines compounds. However, in many cases, especially at low application rates, the fungicidal activity of the known compounds is not satisfactory. Based on this, an object of the present invention is to provide compounds having improved activity and / or a broader activity spectrum against phytopathogenic fungi. Another object of the present invention is to provide fungicides having improved toxicological properties or having improved environmental fate properties.

[0003] These and further objects are achieved by benzodiazepines of formula (I) as defined below compounds and their agriculturally suitable embodiments.

[0004] Accordingly, the present invention relates to compounds of formula I or their N-oxides, tautomers, stereoisomers or agriculturally acceptable salts

[0005]

[0006] Y is N, CR 1 ;

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

[0008] R 2 is in each case independently selected 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;

[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 attached 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 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;

[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 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;

[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] The N-oxides can be prepared from the compounds of the invention according to conventional oxidation methods, for example by treatment of compound I with an organic peracid such as m-chloroperbenzoic acid (see WO 03 / 64572 or J. Med. Chem. 38(11), 1892-903, 1995); or with an inorganic oxidant such as hydrogen peroxide (see J. Heterocyc. Chem. 18(7), 1305-8, 1981) or potassium peroxymonosulfate preparation (see J. Am. Chem. Soc. 123(25), 5962-5973, 2001). 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.

[0034] 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, furthermore phosphonium ions, sulfonium ions, preferably tri(C1-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(C1-C4-alkyl)sulfoxonium.

[0035] 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.

[0036] The compounds of formula I can 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. Furthermore, those skilled in the art know how to separate, enrich and / or selectively prepare the said stereoisomers. The compounds of the invention can exist as a mixture of stereoisomers (e.g. racemates), as individual stereoisomers, or as optically active forms.

[0037] Compounds of formula I may exist in different crystalline modifications, the biological activities of which may differ. They also form part of the subject matter of the present invention.

[0038] As regards the variables, examples of the intermediates obtained during the preparation of compound I correspond to the examples of the compounds of formula I. The term "compound I" refers to the compounds of formula I.

[0039] 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 defined herein independently of one another or more preferably in combination.

[0040] 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 application (e.g. under the action of light, acids or bases). Such conversions may also occur after use, for example in the treated plants in the case of plant treatment or in the harmful fungi to be controlled.

[0041] 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.

[0042] The term "halogen" means fluorine, chlorine, bromine and iodine.

[0043] 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).

[0044] The term "C1-C6-haloalkyl" refers to an alkyl group having 1 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. 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.

[0045] 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.

[0046] The term "C2-C6-haloalkenyl" 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.

[0047] 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.

[0048] The term "C2-C6-haloalkynyl" 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 may be replaced by halogen atoms as described above.

[0049] 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".

[0050] The term "C3-C8-cycloalkyl-C1-C4-alkyl" refers to an alkyl group having 1 to 4 carbon atoms (as defined above), where at least one hydrogen atom of the alkyl group is replaced by a cycloalkyl group having 3 to 8 carbon atoms (as defined above).

[0051] 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, where 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:

[0052] 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

[0053] 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-piperidyl, 3-piperidyl, 4-piperidyl, 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,

[0054] 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- or -4-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.

[0055] The term "substituted" means substituted with 1, 2, 3 or up to the maximum possible number of substituents.

[0056] The term "5- or 6-membered heteroaryl" or "5- or 6-membered heteroaromatic group" means an aromatic ring system that contains, in addition to carbon atoms, 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, O, and S, such as

[0057] 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

[0058] 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.

[0059] 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, specific embodiments of the present invention.

[0060] In addition, with respect to the variables, generally, the embodiments of Compound I are equally applicable to the intermediates.

[0061] According to one embodiment of the compound having the formula I, R 1 is independently selected from H, halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl in each case, and preferably R 1 is independently selected from H, C1-C4-alkyl, C1-C4-haloalkyl in each case, and more preferably R 1 is independently selected from H, C1-C4-alkyl in each case, and most preferably R 1 is H in each case.

[0062] According to one embodiment of the compound having the 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.

[0063] According to one embodiment of the compound of formula I, R 2 Is independently selected from C1-C4-alkyl and C1-C4-haloalkyl in each case, preferably R 2 Is independently selected from H, C1-C4-alkyl, C1-C4-haloalkyl in each case, more preferably R 2 Is independently selected from CH3 and CF2H in each case, most preferably R 2 Is CH3 in each case.

[0064] 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.

[0065] According to yet another embodiment of formula I, R 2 Is F.

[0066] According to yet another embodiment of formula I, R 2 Is Cl.

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

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

[0069] 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.

[0070] According to yet another embodiment of formula I, R 2 Is C1-C6-haloalkyl, especially C1-C4-haloalkyl, such as CF3.

[0071] 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.

[0072] 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.

[0073] In yet another embodiment according to 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 C≡CH, CH2C≡CH, C≡CCl, CH2C≡CCl, or CCl2C≡CCl.

[0074] In another specific embodiment according to formula I, R 2 is an O-C1-C6-alkyl, especially a C1-C4-alkyl, more specifically a C1-C2-alkoxy. R 2 is, for example, OCH3 or OCH2CH3.

[0075] In another specific embodiment according to formula I, R 2 is an O-C1-C6-alkyl.

[0076] In another specific embodiment according to formula I, R 2 is an O-C2-C6-alkenyl, especially a C2-C4-alkenyl, more specifically a C2-C3-alkenyl. R 2 is, for example, OCH=CH2, OCH2CH=CH2.

[0077] In another specific embodiment according to 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, for example, O-CH2-C≡CH.

[0078] In yet another embodiment according to formula I, R 2 is a C3-C6-cycloalkyl, especially cyclopropyl or cyclobutyl.

[0079] In another specific embodiment according to formula I, R 2 is an S-C1-C6-alkyl, especially a C1-C4-alkyl, more specifically a C1-C2-alkoxy. R 2 is, for example, SCH3 or SCH2CH3.

[0080] In another specific embodiment according to formula I, R 2is an S-C1-C6-alkyl group.

[0081] In another specific embodiment according to formula I, R 2 is an S-C2-C6-alkenyl group, particularly a C2-C4-alkenyl group, more particularly a C2-C3-alkenyl group. R 2 is, for example, SCH=CH2, SCH2CH=CH2.

[0082] In another specific embodiment according to formula I, R 2 is an S-C2-C6-alkynyl group, particularly a C2-C6-alkynyl group, particularly a C2-C4-alkynyl group, more particularly a C2-C3-alkynyl group. R 2 is, for example, S-CH2-C≡CH.

[0083] Particularly preferred embodiments of R according to the present invention 2 are 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.

[0084] Table P2:

[0085]

[0086]

[0087] 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, particularly CH3, C2H5, CF3, CH2F, CHF2, cyclopropyl, cyclobutyl, more particularly CH3, CH2F, CF2H, CF3, cyclopropyl, cyclobutyl, and most preferably CH3, CF2H.

[0088] In yet another embodiment according to formula I, R 3 is a C1-C6-alkyl group, particularly a C1-C4-alkyl group, such as CH3 or C2H5, particularly CH3 or CH2CH3.

[0089] In yet another embodiment according to formula I, R 3 is a C1-C6-haloalkyl group, particularly a C1-C4-haloalkyl group, such as CF3, FCH2, F2CH, CF3CH2.

[0090] 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.

[0091] In yet another embodiment according to formula I, R 3 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.

[0092] 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 such as OCH3 or OCH2CH3.

[0093] 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 such as OCH=CH2, OCH2CH=CH2.

[0094] 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 such as O-CH2-C≡CH.

[0095] 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.

[0096] In yet another embodiment according to formula I, R 3 is C3-C6 cycloalkyl, especially cyclopropyl, cyclobutyl.

[0097] 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 such as SCH3 or SCH2CH3.

[0098] In another specific embodiment according to formula I, R 3 is S-C1-C6 alkyl.

[0099] 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.

[0100] 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-C≡CH.

[0101] 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.

[0102] Table P3:

[0103]

[0104] 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.

[0105] 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 ; where each R 5a is independently halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl or O-C1-C6-alkyl.

[0106] 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 the phenyl and CH2-phenyl are unsubstituted or substituted by one or two halogens.

[0107] According to a further embodiment of the compound of formula I, R 5 is CH3 or CF3.

[0108] According to a further embodiment of the compound of formula I, R 5 is CH3.

[0109] 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.

[0110] According to a further embodiment of the compound of formula I, R 5 is CH=CH2, CH2CH=CH2.

[0111] 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.

[0112] 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.

[0113] According to one embodiment of the compound of formula I, R 6Independently selected in each case 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).

[0114] 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.

[0115] 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, where the cycloalkyl or heterocycle may be unsubstituted or substituted by halogen, C1-C6-alkyl, C1-C6-haloalkyl.

[0116] According to a further embodiment of the compound of formula I, R 5 and R 6 form a C3-C6-cycloalkyl (Example 6.4).

[0117] 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.

[0118] According to a further embodiment of the compound of formula I, R 5 and R 6 together form a (=O) group (Example 6.5).

[0119] Preferred embodiments of R 5 and R 6 according to the invention are given in Table P5 below, where each row from P5-1 to P5-19 corresponds to a specific embodiment of the invention, and where P5-1 to P5-19 in any combination with each other are preferred embodiments of the invention. The point of attachment of the carbon atom to which R 5 and R 6 are bonded is marked with "#" in the figure.

[0120] Table P5,6:

[0121]

[0122]

[0123] According to one embodiment of the compound of 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.

[0124] According to one embodiment of the compound of 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 the phenyl and CH2-phenyl are unsubstituted or substituted by one or two halogens.

[0125] According to a further embodiment of the compound of formula I, R 7 is CH3 or CF3.

[0126] According to a further embodiment of the compound of formula I, R 7 is CH3.

[0127] According to a further embodiment of the compound of 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.

[0128] According to a further embodiment of the compound of formula I, R 7 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.

[0129] According to one embodiment of the compound of formula I, R8 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, a five- or six-membered heteroaryl or a five- or six-membered CH2-heteroaryl in each case; 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.

[0130] According to one embodiment of the compound of formula I, R 8 is independently selected 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) in each case.

[0131] 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.

[0132] 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.

[0133] According to a further embodiment of the compound of formula I, R 7 and R 8 form a C3-C6-cycloalkyl (Example 8.4).

[0134] 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 from the group consisting of O and S.

[0135] According to a further embodiment of the compound of formula I, R 7 and R 8 together form a (=O) group (Example 8.5).

[0136] Preferred embodiments of R 7 and 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 any combination of P7-1 to P7-19 with each other is a preferred embodiment 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.

[0137] Table P7,8:

[0138]

[0139] According to a further embodiment of the compound of formula I,

[0140] R 9 is in each case independently selected from 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;

[0141] wherein

[0142] R 9ais 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.

[0143] In yet another embodiment according to formula I, R 9 is Cl, F.

[0144] In yet another embodiment according to formula I, R 9 is CN, CH2CN or CH(CH3)CN.

[0145] In another specific embodiment according to formula I, R 9 is CH(=O).

[0146] In another specific embodiment according to formula I, R 9 is OCH3 or OCH2CH3.

[0147] In another specific embodiment according to formula I, R 9 is C(=O)C1-C6-alkyl, where the alkyl is CH3, C2H5, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl or isopentyl.

[0148] In another specific embodiment according to formula I, R 9 is C(=O)C2-C6-alkenyl, where the alkenyl is CH=CH2, CH2CH=CH2.

[0149] In another specific embodiment according to formula I, R 9 is C(=O)C2-C6-alkynyl, where the alkynyl is C≡CH, CH2C≡CH.

[0150] 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).

[0151] 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.

[0152] In yet another embodiment according to formula I, R 9is a C1-C6-alkyl group, such as CH3, C2H5, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl or isopentyl.

[0153] In yet another embodiment according to formula I, R 9 is a C1-C6-alkyl group, especially a C1-C4-alkyl group, such as CH3, C2H5, n-propyl, isopropyl.

[0154] In yet another embodiment according to formula I, R 9 is a C1-C6-haloalkyl group, especially a C1-C4-haloalkyl group, such as CF3, CCl3, FCH2, ClCH2, F2CH, Cl2CH, CF3CH2, CCl3CH2 or CF2CHF2.

[0155] In yet another embodiment according to formula I, R 9 is a C3-C6-cycloalkyl group, especially cyclopropyl.

[0156] In yet another embodiment according to formula I, R 9 is a C3-C6-halocycloalkyl group. In a specific embodiment, R 9b is a fully or partially halogenated cyclopropyl group, such as 1-F-cyclopropyl, 1-Cl-cyclopropyl, 1,1-F2-cyclopropyl, 1,1-Cl2-cyclopropyl.

[0157] In yet another embodiment according to formula I, R 9 is a C2-C6-alkenyl group, especially a C2-C4-alkenyl group, such as CH=CH2, C(CH3)=CH2, CH2CH=CH2.

[0158] In another specific embodiment according to formula I, R 9 is a C2-C6-haloalkenyl group, especially a C2-C4-haloalkenyl group, more specifically a C2-C3-haloalkenyl group, 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.

[0159] In yet another embodiment according to formula I, R 9 is a C2-C6-alkynyl group or a C2-C6-haloalkynyl group, especially a C2-C4-alkynyl group or a C2-C4-haloalkynyl group, such as C≡CH, CH2C≡CH.

[0160] In yet another embodiment according to formula I, R 9 is -S(=O)2-R 9a wherein R9a Preferably a C1-C6-alkyl group, especially a C1-C4-alkyl group such as CH3, C2H5, n-propyl, isopropyl.

[0161] In yet another embodiment according to formula I, R 9 is an aryl group, especially a phenyl group, wherein the aryl or phenyl moiety is in each case unsubstituted or substituted by the same or different groups R which are independently selected from the following 9b substituents: halogen, C1-C2-alkyl, C1-C2-alkoxy, C1-C2-haloalkyl and C1-C2-haloalkoxy, especially F, Cl, Br, CH3, OCH3, CF3 and OCF3. According to one embodiment, R 9 is an unsubstituted phenyl group. According to another embodiment, R 9 is a phenyl group substituted by one, two or three (especially one) halogen atoms especially selected from F, Cl and Br, more specifically selected from F and Cl.

[0162] In yet another embodiment according to formula I, R 9 is a 5-membered heteroaryl group 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.

[0163] In yet another embodiment according to formula I, R 9 is a 6-membered heteroaryl group 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.

[0164] In yet another embodiment according to formula I, R 9independently 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 R 9 the acyclic part of is unsubstituted or substituted by the same or different groups R as defined and preferably as defined herein 9a and where R 9 the carbocyclic, phenyl and heteroaryl parts of are unsubstituted or substituted by the same or different groups R as defined and preferably as defined herein 9b substituted.

[0165] Particularly preferred embodiments of R according to the invention are in Table P9 below, where each row from P9-1 to P9-31 corresponds to a specific embodiment of the invention, and where P9-1 to P9-31 can also be combined with each other arbitrarily 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. 9

[0166] Table P9:

[0167]

[0168] 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).

[0169] According to one embodiment of the compound of formula I, X is independently selected in each case from halogen, O-C1-C6-alkyl.

[0170] According to one embodiment of the compound of formula I, X is independently selected in each case from F or Cl.

[0171] According to one embodiment of the compound of formula I, X is C3-C6-cycloalkyl.

[0172] According to one embodiment of the compound of formula I, n is 0.

[0173] According to one embodiment of the compound of formula I, n is 1.

[0174] According to one embodiment of the compound of formula I, n is 2.

[0175] According to one embodiment, Xn is defined as follows:​

[0176]

[0177] And X is selected from F, Cl, I, CH3, cyclopropyl, CH=CH2, C≡CH, OCH3, OCHF2, CF3, CHF2, CH2CH3, CN.

[0178] According to one embodiment, Xn is defined as follows:

[0179]

[0180] And X is F.

[0181] According to one embodiment, Xn is defined as follows:

[0182]

[0183] And X is selected from F, Cl, I, CH3, cyclopropyl, CH=CH2, C≡CH, OCH3, OCHF2, CF3, CHF2, CH2CH3, CN.

[0184] According to one embodiment, Xn is defined as follows:

[0185]

[0186] And X is F.

[0187] According to one embodiment, n is 0.

[0188] In a further aspect, the present invention relates to Examples E.1 to E.275 listed in Table E, which represent preferred combinations of the examples defined above for each of the variables R 2 、R 3 and X (represented by Examples X.1 to X.6), and n in the compounds of formula I is defined as follows.

[0189]

[0190] Table E:

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203] In another aspect, the present invention relates to Examples E.1 to E.275 listed in Table E, wherein R 5 is represented by Example 5.1, and R 6 is represented by Example 6.1.

[0204] In another aspect, the present invention relates to Examples E.1 to E.275 listed in Table E, wherein R 5 is represented by Example 5.2, and R 6 is represented by Example 6.1.

[0205] In another aspect, the present invention relates to Examples E.1 to E.275 listed in Table E, wherein R 5 is represented by Example 5.3, and R 6 is represented by Example 6.1.

[0206] In another aspect, the present invention relates to Examples E.1 to E.275 listed in Table E, wherein R 5 is represented by Example 5.4, and R 6 is represented by Example 6.1.

[0207] In another aspect, the present invention relates to Examples E.1 to E.275 listed in Table E, wherein R 5 is represented by Example 5.1, and R 6 is represented by Example 6.2.

[0208] In another aspect, the present invention relates to Examples E.1 to E.275 listed in Table E, wherein R 5 is represented by Example 5.2, 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, wherein R 5 is represented by Example 5.3, and R 6Represented 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 5.4, 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 5.1, and R 6 is represented by Example 6.3.

[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 5.2, 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 5.3, 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 5.4, 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 and R 6 are represented by Example 6.4.

[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 6.5.

[0217] 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.

[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 7.2, 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 7.3, 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 7.4, 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 7.1, and R 8 is represented by Example 8.2.

[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 7.2, 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 7.3, 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 7.4, 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 R 7 is represented by Example 7.1, and R 8 is represented by Example 8.3.

[0226] 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 8.3.

[0227] 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 8.3.

[0228] In a further aspect, the 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.

[0229] In a further aspect, the 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.

[0230] In a further aspect, the 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.

[0231] In particular, considering their use, according to one embodiment, it is preferred to compile the following compounds in Tables 1a to 12a: Compounds I.A-1, I.A-2, I.A-3, I.A-4, I.A-5, I.A-6, I.A-7, I.A-8. In addition, each group mentioned for the substituents in the table by itself (independent of the combinations mentioned) is a particularly preferred aspect of the substituents.

[0232]

[0233] Table 1a Compounds of formulae I.A-1, I.A-2, I.A-3, I.A-4, I.A-5, I.A-6, I.A-7, I.A-8, wherein R 9 is CH3, and the meanings of the combinations of X 1 , X 2 , R 5 , R 6 , R 7 and R 8 for each individual compound correspond in each case to a row of Table B (Compounds I.A-1.1a.B-1 to I.A-1.1a.B-784, I.A-2.1a.B-1 to I.A-2.1a.B-784, I.A-3.1a.B-1 to I.A-3.1a.B-784, I.A-4.1a.B-1 to I.A-4.1a.B-784, I.A-5.1a.B-1 to I.A-5.1a.B-784, I.A-6.1a.B-1 to I.A-6.1a.B-784, I.A-7.1a.B-1 to I.A-7.1a.B-784, I.A-8.1a.B-1 to I.A-8.1a.B-784).

[0234] Table 2a has compounds of formulae I.A-1, I.A-2, I.A-3, I.A-4, I.A-5, I.A-6, I.A-7, I.A-8, wherein R 9 is CH2CH3, and the meaning of the combination of each individual compound's X 1 , X 2 , R 5 , R 6 , R 7 and R 8 corresponds to a row of Table B in each case (compounds I.A-1.2a.B-1 to I.A-1.2a.B-784, I.A-2.2a.B-1 to I.A-2.2a.B-784, I.A-3.2a.B-1 to I.A-3.2a.B-784, I.A-4.2a.B-1 to I.A-4.2a.B-784, I.A-5.2a.B-1 to I.A-5.2a.B-784, I.A-6.2a.B-1 to I.A-6.2a.B-784, I.A-7.2a.B-1 to I.A-7.2a.B-784, I.A-8.2a.B-1 to I.A-8.2a.B-784).

[0235] Table 3a has compounds of formulae I.A-1, I.A-2, I.A-3, I.A-4, I.A-5, I.A-6, I.A-7, I.A-8, wherein R 9 is CH2CH2CH3, and the meaning of the combination of each individual compound's X 1 , X 2 , R 5 , R 6 , R 7 and R 8 corresponds to a row of Table B in each case (compounds I.A-1.3a.B-1 to I.A-1.3a.B-784, I.A-2.3a.B-1 to I.A-2.3a.B-784, I.A-3.3a.B-1 to I.A-3.3a.B-784, I.A-4.3a.B-1 to I.A-4.3a.B-784, I.A-5.3a.B-1 to I.A-5.3a.B-784, I.A-6.3a.B-1 to I.A-6.3a.B-784, I.A-7.3a.B-1 to I.A-7.3a.B-784, I.A-8.3a.B-1 to I.A-8.3a.B-784)

[0236] Table 4a has compounds of formulae I.A-1, I.A-2, I.A-3, I.A-4, I.A-5, I.A-6, I.A-7, I.A-8, wherein R 9is CN, and for each individual compound, X 1 , X 2 , R 5 , R 6 , R 7 and R 8 in each case corresponds to a row in Table B (Compounds I.A-1.4a.B-1 to I.A-1.4a.B-784, I.A-2.4a.B-1 to I.A-2.4a.B-784, I.A-3.4a.B-1 to I.A-3.4a.B-784, I.A-4.4a.B-1 to I.A-4.4a.B-784, I.A-5.4a.B-1 to I.A-5.4a.B-784, I.A-6.4a.B-1 to I.A-6.4a.B-784, I.A-7.4a.B-1 to I.A-7.4a.B-784, I.A-8.4a.B-1 to I.A-8.4a.B-784).

[0237] Table 5a has compounds of formula I.A-1, I.A-2, I.A-3, I.A-4, I.A-5, I.A-6, I.A-7, I.A-8, where R 9 is CH2CN, and for each individual compound, X 1 , X 2 , R 5 , R 6 , R 7 and R 8 in each case corresponds to a row in Table B (Compounds I.A-1.5a.B-1 to I.A-1.5a.B-784, I.A-2.5a.B-1 to I.A-2.5a.B-784, I.A-3.5a.B-1 to I.A-3.5a.B-784, I.A-4.5a.B-1 to I.A-4.5a.B-784, I.A-5.5a.B-1 to I.A-5.5a.B-784, I.A-6.5a.B-1 to I.A-6.5a.B-784, I.A-7.1a.B-1 to I.A-7.5a.B-784, I.A-8.5a.B-1 to I.A-8.5a.B-784).

[0238] Table 6a has compounds of formula I.A-1, I.A-2, I.A-3, I.A-4, I.A-5, I.A-6, I.A-7, I.A-8, where R 9 is CHO, and for each individual compound, X 1 , X 2 , R 5 , R 6 , R 7 and R8 The meaning of the combination corresponds to a row in Table B in each case (compounds I.A-1.6a.B-1 to I.A-1.6a.B-784, I.A-2.6a.B-1 to I.A-2.6a.B-784, I.A-3.6a.B-1 to I.A-3.6a.B-784, I.A-4.6a.B-1 to I.A-4.6a.B-784, I.A-5.6a.B-1 to I.A-5.6a.B-784, I.A-6.6a.B-1 to I.A-6.6a.B-784, I.A-7.6a.B-1 to I.A-7.6a.B-784, I.A-8.1′6a.B-1 to I.A-8.6a.B-784)

[0239] Table 7a shows compounds of formula I.A-1, I.A-2, I.A-3, I.A-4, I.A-5, I.A-6, I.A-7, I.A-8, where R 9 is C(CH3)3, and for each individual compound, X 1 、X 2 、R 5 、R 6 、R 7 and R 8 The meaning of the combination corresponds to a row in Table B in each case (compounds I.A-1.7a.B-1 to I.A-1.7a.B-784, I.A-2.7a.B-1 to I.A-2.7a.B-784, I.A-3.7a.B-1 to I.A-3.7a.B-784, I.A-4.7a.B-1 to I.A-5.7a.B-784, I.A-5.7a.B-1 to I.A-5.7a.B-784, I.A-6.7a.B-1 to I.A-6.7a.B-784, I.A-7.7a.B-1 to I.A-7.7a.B-784, I.A-8.7a.B-1 to I.A-8.7a.B-784)

[0240] Table 8a shows compounds of formula I.A-1, I.A-2, I.A-3, I.A-4, I.A-5, I.A-6, I.A-7, I.A-8, where R 9 is COCH3, and for each individual compound, X 1 、X 2 、R 5 、R 6 、R 7 and R 8The meaning of the combination in each case corresponds to a row in Table B (Compounds I.A-1.8a.B-1 to I.A-1.8a.B-784, I.A-2.8a.B-1 to I.A-2.8a.B-784, I.A-3.8a.B-1 to I.A-3.8a.B-784, I.A-4.8a.B-1 to I.A-5.8a.B-784, I.A-5.8a.B-1 to I.A-5.8a.B-784, I.A-6.8a.B-1 to I.A-6.8a.B-784, I.A-7.8a.B-1 to I.A-7.8a.B-784, I.A-8.8a.B-1 to I.A-8.8a.B-784)

[0241] Table 9a Compounds of formula I.A-1, I.A-2, I.A-3, I.A-4, I.A-5, I.A-6, I.A-7, I.A-8, 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 to a row in Table B (Compounds I.A-1.9a.B-1 to I.A-1.9a.B-784, I.A-2.9a.B-1 to I.A-2.9a.B-784, I.A-3.9a.B-1 to I.A-3.9a.B-784, I.A-4.9a.B-1 to I.A-5.9a.B-784, I.A-5.9a.B-1 to I.A-5.9a.B-784, I.A-6.9a.B-1 to I.A-6.9a.B-784, I.A-7.9a.B-1 to I.A-7.9a.B-784, I.A-8.9a.B-1 to I.A-8.9a.B-784)

[0242] Table 10a Compounds of formula I.A-1, I.A-2, I.A-3, I.A-4, I.A-5, I.A-6, I.A-7, I.A-8, 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 in each case corresponds to a row in Table B (compounds I.A-1.10a.B-1 to I.A-1.10a.B-784, I.A-2.10a.B-1 to I.A-2.10a.B-784, I.A-3.10a.B-1 to I.A-3.10a.B-784, I.A-4.10a.B-1 to I.A-5.10a.B-784, I.A-5.10a.B-1 to I.A-5.10a.B-784, I.A-6.10a.B-1 to I.A-6.10a.B-784, I.A-7.10a.B-1 to I.A-7.10a.B-784, I.A-8.10a.B-1 to I.A-8.10a.B-784)

[0243] Table 11a Compounds of formula I.A-1, I.A-2, I.A-3, I.A-4, I.A-5, I.A-6, I.A-7, I.A-8, where R 9 is CH2CCH, and for each individual compound, the meaning of X 1 、X 2 、R 5 、R 6 、R 7 and R 8 The meaning of the combination in each case corresponds to a row in Table B (compounds I.A-1.11a.B-1 to I.A-1.11a.B-784, I.A-2.11a.B-1 to I.A-2.11a.B-784, I.A-3.11a.B-1 to I.A-3.11a.B-784, I.A-4.11a.B-1 to I.A-5.11a.B-784, I.A-5.11a.B-1 to I.A-5.11a.B-784, I.A-6.11a.B-1 to I.A-6.11a.B-784, I.A-7.11a.B-1 to I.A-7.11a.B-784, I.A-8.11a.B-1 to I.A-8.11a.B-784)

[0244] Table 12a Compounds of formula I.A-1, I.A-2, I.A-3, I.A-4, I.A-5, I.A-6, I.A-7, I.A-8, where R 9 is CH2C6H5, and for each individual compound, the meaning 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-1.12a.B-1 to I.A-1.12a.B-784, I.A-2.12a.B-1 to I.A-2.12a.B-784, I.A-3.12a.B-1 to I.A-3.12a.B-784, I.A-4.12a.B-1 to I.A-5.12a.B-784, I.A-5.12a.B-1 to I.A-5.12a.B-784, I.A-6.12a.B-1 to I.A-6.12a.B-784, I.A-7.1a.B-1 to I.A-7.12a.B-784, I.A-8.12a.B-1 to I.A-8.12a.B-7842) Table B

[0245]

[0246]

[0247]

[0248]

[0249]

[0250]

[0251]

[0252]

[0253]

[0254]

[0255]

[0256]

[0257]

[0258]

[0259]

[0260]

[0261]

[0262]

[0263]

[0264]

[0265]

[0266]

[0267]

[0268]

[0269]

[0270]

[0271]

[0272]

[0273]

[0274]

[0275]

[0276] 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.

[0277] For example, compound I can be obtained via a benzodiazepine represented by formula (2): The benzodiazepines are prepared by alkylation or acylation with a series of alkyl halides and acyl chlorides. Class (2) is achieved by deprotonation with a range of organic or inorganic bases such as potassium tert-butoxide or sodium hydride. The reaction is preferably carried out at 0°C to room temperature, in some cases, slowly reacting at temperatures up to 60°C and using 1-5 equivalents of base and 1-3 equivalents of alkylating / acylating agent, as described in Chem. Eur. J. [European Journal of Chemistry] (2016), 22, 10607-10613, CN 114349714 A, WO 2008 / 118141A2, or US2012 / 184732 A1.

[0278]

[0279] The benzodiazepine represented by formula (2) compounds can be prepared by reacting a series of diamines (or their HCl salts) represented by formula (4) with a pyridyl / pyrazinyl aryl ketone (3) substituted by at least 1 halogen (represented by X 1 , preferably F) in the presence of a base. This reaction is preferably carried out at room temperature to 120 °C with 1 - 6 equivalents of base and 1 to 1.5 equivalents of diamine, similar to the methods described in WO 2016 / 87370A1, Org. Biomol. Chem. [Organic and Biomolecular Chemistry] (2014), 12, 6895 - 6900, WO2006 / 44753A2 or Heterocycles [Heterocycles] (1994), 38, 125 - 134.

[0280]

[0281] Aryl ketone (3) is commercially available or can be prepared according to the scheme by oxidizing aryl alcohol 5 using, for example, manganese dioxide, as described in Inorganica Chimica Acta [Inorganic Chemistry Acta] (2012), 382, 72 - 78, WO 2000 / 038618, CN 107879989 A, or Chinese Science Bulletin [Chinese Science Bulletin] 2010, 55(25), 2817 - 2819.

[0282]

[0283] Aryl alcohol (5) can be prepared by isopropylmagnesium chloride - mediated bromine / iodine - magnesium exchange of 7, and then added to a commercially available aldehyde represented by the general formula (6). This reaction is preferably carried out at 0 °C using an equimolar ratio of iPrMgCl to aryl halide (7), and the intermediate of this aryl halide is used at a ratio of 1.2 - 1.3:1 relative to aldehyde (6), as described in WO 2021 / 71821A1, J. Med. Chem. [Journal of Medicinal Chemistry], (2013), 56, 10158 - 10170, WO 2014 / 102233 A1, or US2016 / 83401A1.

[0284]

[0285] Alternatively, the scaffold represented by formula (2) can also be obtained by reacting aryl ketone (3) with partially protected diamine (8) in the presence of an organic or inorganic base at a temperature up to 200 °C under microwave irradiation, as described in US2006 / 178386A1, Bioorganic & Medicinal Chemistry Letters (2021), 35, 127813, Chem. Sci. (2021), 12, 4519-4525, or J. Org. Chem. (2005), 70, 8924-8931. The resulting product 9 can then be further reacted at 0 °C in a 1.5:7 mixture of TFA:DCM to produce the condensation product represented by formula 2, as described in US2006 / 3995, J. Bioorg. Med. Chem. Lett. (2007), 17, 2527-2530, WO 2022 / 99011A1, Org Lett. (2012), 14, 5916-5919, or J. Med. Chem. (2016), 59, 10661-10675. Alkylation / acylation can then be carried out as described above to obtain compound I.

[0286]

[0287] Compound I and its compositions are suitable as fungicides, respectively, 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 as foliar fungicides, seed dressing fungicides, and soil fungicides in crop protection.

[0288] Compound I and its compositions can preferably be used to control phytopathogenic fungi on the following: various cultivated plants, such as cereals, for example wheat, rye, barley, triticale, oats or rice; sugar beet, such as sugar beet or fodder beet; fruits, such as pomaceous fruits (apples, pears, etc.), stone fruits (e.g., plums, peaches, apricots, 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, olives, sunflowers, coconuts, cocoa beans, castor oil plants, oil palms, peanuts or soybeans; cucurbits, such as 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; laurel family plants, such as avocados, cinnamon or camphor; energy and raw material plants, such as corn, soybeans, rape, sugar cane or oil palms; corn; tobacco; nuts; coffee; tea; bananas; grapevines (table grape and 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 evergreens (conifers, eucalyptus, etc.); plant propagation materials such as seeds; and crop materials of these plants.

[0289] More preferably, compound I and its compositions are respectively used to control fungi on the following: field crops such as potatoes, sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rape, beans, sunflowers, coffee or sugar cane; fruits; vines; ornamental plants; or vegetables, such as cucumbers, tomatoes, green beans or pumpkins.

[0290] The term "plant propagation material" should be understood to mean all reproductive parts of plants, such as seeds; and vegetative plant material that 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 after germination or emergence for transplantation.

[0291] Preferably, plant propagation materials are respectively treated with compound I and its compositions to control fungi on the following: cereals such as wheat, rye, barley and oats; rice, corn, cotton and soybeans.

[0292] According to the present invention, all the above cultivated plants should be understood to include all species, subspecies, varieties, cultivars and / or hybrids belonging to the corresponding 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.

[0293] Maize, also known as Indian corn or Zea mays, includes all types of maize such as forage maize and sweet corn. According to the present invention, it includes all Zea mays or maize subspecies and / or varieties, in particular floury maize (Zea mays var. amylacea), popcorn (Zea mays var. everta), dent maize (Zea mays var. indentata), flint maize (Zea mays var. indurata), sweet corn (Zea mays var. saccharata and var. rugosa), waxy maize (Zea mays var. ceratina), high amylose maize (amylomaize) (high amylose Zea mays variety), pod maize or wild maize (Zea mays var. tunicata) and striped maize (Zea mays var. japonica).

[0294] Most soybean cultivars can be classified into 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. According to the present invention, it includes all soybean cultivars or varieties, in particular indeterminate and determinate cultivars or varieties.

[0295] The term "cultivated plant" shall be understood to include plants that have been modified by mutagenesis or genetic engineering in order to confer new traits on the plant 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 techniques to generate modifications in the plant genome that cannot be readily obtained by crossing, mutagenesis or natural recombination in the natural environment. Typically, one or more genes are integrated into the plant genome in order to add traits or to 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 at which 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.

[0296] 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 using transgenes.

[0297] 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 oxynil 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.

[0298] 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 herbicide tolerance genes include but are not limited to 19-51a, 31707, 42317, 81910, 281-24-236, 3006-210-23, BXN10211, BXN10215, BXN10222, BXN10224, MON1445, MON1698, MON88701, MON88913, GHB119, GHB614, LLCotton25, T303-3 and T304-40. Transgenic canola events containing herbicide tolerance genes are, for example, but not excluding others, MON88302, HCR-1, HCN10, HCN28, HCN92, MS1, MS8, PHY14, PHY23, PHY35, PHY36, RF1, RF2 and RF3.

[0299] Transgenes conferring 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, transgenes of plant origin can be used, such as genes encoding protease inhibitors, such as CpTI and pinII. Another approach uses transgenes such as dvsnf7 to produce double-stranded RNA in plants.

[0300] Transgenic maize events containing insecticidal protein genes or double-stranded RNA include but are not limited to Bt10, Bt11, Bt176, MON801, MON802, MON809, MON810, MON863, MON87411, MON88017, MON89034, 33121, 4114, 5307, 59122, TC1507, TC6275, CBH-351, MIR162, DBT418 and MZIR098. Transgenic soybean events containing 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.

[0301] Cultivated plants with increased yield have been produced by using the transgenes athb17 (e.g., maize event MON87403) or bbx32 (e.g., soybean event MON87712).

[0302] 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).

[0303] Tolerance to abiotic conditions (such as drought) has been achieved by using the transgenes cspB (maize event MON87460) and Hahb-4 (soybean event ) generated.

[0304] Traits are typically combined to produce cultivated plants having stacked traits by combining gene combinations in transformation events or by combining different events during a breeding process. 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 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.

[0305] 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 on 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 on specific events and methods for detecting these 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, WO 13 / 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 the 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, they can be found in 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 the potato events E12, F10, J3, J55, V11, X17, Y9, they can be found in WO 14 / 178910, WO 14 / 178913, WO 14 / 178941, WO 14 / 179276, WO 16 / 183445, WO 17 / 062831, WO 17 / 062825; for the rice events LLRICE06, LLRICE601, LLRICE62, they can be found in WO 00 / 026345, WO 00 / 026356, WO 00 / 026345;And for 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.;

[0306] The separate use of Compound I and its compositions on cultivated plants can lead to effects specific to cultivated plants comprising 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 in particular 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.

[0307] Compound I and its compositions are particularly suitable, respectively, for controlling the causative agents of the following plant diseases:

[0308] 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 (formerly known as Dactylium dendroides), teleomorph: Nectria albertinii, Nectria rosella synonym Hypomyces rosellus); Cladosporium species on tomato (e.g., Cladosporium fulvum: leaf mold) and cereals, e.g., Cladosporium herbarum on wheat (black ear); Claviceps purpurea on cereals (ergot); Cochliobolus (anamorph: Helminthosporium of the genus Bipolaris) species on maize (Cochliobolus carbonum), cereals (e.g., Cochliobolus sativus, anamorph: Bipolaris sorokiniana) and rice (e.g., Cochliobolus miyabeanus, anamorph: Helminthosporium oryzae) (leaf spot); cotton (e.g., Colletotrichum gossypii), maize (e.g., Colletotrichum graminicola: anthracnose stalk rot), soft fruits, potato (e.g., Colletotrichum coccodes: black dot), common bean (e.g., Colletotrichum lindemuthianum), soybean (e.g., Colletotrichum truncatum or Colletotrichum gloeosporioides), vegetables (e.g., Colletotrichum lagenarium or Colletotrichum capsici), fruits (e.g., Colletotrichum acutatum), coffee (e.g., Colletotrichum coffeanum or Colletotrichum kahawae) and various crops (ColletotrichumSpecies of Colletotrichum (teleomorph: Glomerella) on [[species name not provided]] (anthracnose); species of Corticium, such as C. sasakii on rice (sheath blight); Corynespora cassiicola on soybean, cotton and ornamental plants (leaf spot); species of Cycloconium, such as C. oleaginum on olive trees; species of Cylindrocarpon on fruit trees, vines (e.g., C. liriodendri, teleomorph: Neonectria liriodendri: Black Foot Disease) and ornamental plants (e.g., fruit tree canker or young vine decline, teleomorph: species of Nectria or Neonectria); Dematophora necatrix on soybean (teleomorph: Rosellinia necatrix) (root and stem rot); species of Diaporthe, such as D. phaseolorum on soybean (damping-off); species of Drechslera (synonym Helminthosporium, teleomorph: Pyrenophora) on maize, 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;veneta): Elsinoe species on anthracnose and vines (Elsinoe ampelina: anthracnose); Entyloma oryzae on rice (leaf smut); Epicoccum species on wheat (black mold); Erysiphe species (powdery mildew) on sugar beet (Erysiphe betae), vegetables (e.g., Erysiphe pisi on peas), such as cucurbits (e.g., Erysiphe cichoracearum), cabbage, rape (e.g., Erysiphe cruciferarum); Eutypa lata (Eutypa canker or dieback, anamorph: Cytosporina lata, synonym Libertella blepharis) on fruit trees, vines and ornamental woods; Exserohilum (synonym Helminthosporium) species on maize (e.g., Exserohilum turcicum); Fusarium (sexual form: Gibberella) species (wilt, root or stem rot) on various plants, 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; Gibberella species 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 cottongossypii); Grain staining complex on rice; Guignardia bidwellii (black rot) on vines; Gymnosporangium species on Rosaceae plants and junipers, such as Gymnosporangium sabinae (rust) on pears; Helminthosporium species (synonym Drechslera, teleomorph: Cochliobolus) on maize, cereals, potatoes and rice; Hemileia species, such as Hemileia vastatrix (coffee leaf rust) on coffee; 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 groundnuts, such as Mycosphaerella graminicola on wheat (anamorph: Zymoseptoria tritici, previously known as Septoria tritici: Septoria leaf blotch), or Mycosphaerella fijiensis (synonym Pseudocercospora fijiensis: black Sigatoka disease) and Mycosphaerella musicola on bananas, Mycosphaerella arachidicola (synonym M. arachidis or Cercospora arachidis) on groundnuts, Mycosphaerella berkeleyi, Mycosphaerella pisi on peas and Mycosphaerella brassiciola on Brassica; Brassica oleracea (e.g. Peronospora parasiticaSpecies of Peronospora (downy mildew) on Brassica species (e.g., Peronospora parasitica on Brassica brassicae), rape (e.g., Peronospora parasitica on Brassica napus), onion (e.g., Peronospora destructor on Allium cepa), tobacco (Peronospora tabacina on Nicotiana tabacum), and soybean (e.g., Peronospora manshurica on Glycine max); Phakopsora pachyrhizi and Phakopsora meibomiae on soybean (soybean rust); Species of Phialophora, such as on vines (e.g., Phialophora tracheiphila and Phialophora tetraspora) and soybean (e.g., Phialophora gregata: stem rot); Phoma lingam (synonyms Leptosphaeria biglobosa and Leptosphaeria maculans: rhizome 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; Species of Phomopsis on sunflower, vines (e.g., Phomopsis viticola: cane and leaf spot) and soybean (e.g., stem rot: Phomopsis phaseoli, teleomorph: Diaporthe phaseolorum); Physoderma maydis on maize (brown spot); Species of Phytophthora (wilt, root, leaf, fruit, and stem rot) on various plants, such as red pepper and gourd (e.g., Phytophthora capsici), soybean (e.g., Phytophthora megasperma, synonym Phytophthora sojae), potato and tomato (e.g., Phytophthora infestans: late blight), and broad-leaved trees (e.g., Phytophthora ramorum: sudden oak death); Plasmodiophora brassicae (club root) on cabbage, rape, radish, and other plants; Species of Plasmopara, such as Plasmopara viticola on vines (grapevine downy mildew) and Plasmopara halstedii on sunflower; Species of Podosphaera (powdery mildew) on Rosaceae plants, hops, pome fruits, and soft fruits, such as Podosphaera leucotricha on apple and Podosphaera xanthii on gourdPolymyxa species on, for example, cereals such as barley and wheat (P. graminis) and sugar beet (P. betae), and the 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, for example P. cubensis on cucurbits or P. humili on hops; Pseudopezicula tracheiphila (red fire disease or rotbrenner, anamorph: Phialophora) on vines; Puccinia species (rust) on various plants, for example P. triticina (brown rust or leaf rust), P. striiformis (stripe rust or yellow rust), P. hordei (dwarf rust), P. graminis (stem rust or black rust) or P. recondita (brown rust or leaf rust) on cereals such as wheat, barley or rye, P. kuehnii (citrus rust) on sugar cane and P. asparagi on asparagus; Pyrenopeziza species, for example P. brassicae on oilseed rape; Pyrenophora tritici-repentis (anamorph: Drechslera tritici-repentis) (tan spot) on wheat or P. teres (net blotch) on barley; Pyricularia species, for example P. oryzae on rice (teleomorph: Magnaporthe grisea: rice blast), and P. grisea on turfgrass and cereals; Pythium species (damping-off) (for example P. ultimum or P. aphanidermatum) on turfgrass, rice, maize, wheat, cotton, oilseed rape, sunflower, soybean, sugar beet, vegetables and various other plants, and P. oligandrum on mushroomsoligandrum); Ramularia species, such as R. collo-cygni on barley (Ramularia leaf spot, physiological leaf spot), R. areola on cotton (teleomorph: Mycosphaerella areola), and R. beticola on sugar beet; Rhizoctonia species on cotton, rice, potato, turfgrass, maize, oilseed rape, potato, sugar beet, vegetables, and many other plants, such as R. solani on soybean (rhizome rot), R. solani on rice (sheath blight), or R. cerealis on wheat or barley (Rhizoctonia spring leaf blight); Rhizopus stolonifer (black mold, soft rot) on strawberry, carrot, cabbage, vine, and tomato; Rhynchosporium secalis and R. commune (scald) on barley, rye, and triticale; Sarocladium oryzae and S. attenuatum on rice (sheath rot); Sclerotinia species (stem rot or white mold) on vegetables (S. minor and S. sclerotiorum) and field crops, such as oilseed rape, sunflower (e.g., S. sclerotiorum), and soybean; Sclerotium rolfsii (synonym Athelia rolfsii) on soybean, peanut, vegetables, maize, cereals, and ornamental plants; Septoria species on many plants, such as S. glycines on soybean (brown spot), S. tritici on wheat (synonym Zymoseptoria tritici, Septoria leaf blotch), and S. nodorum on cereals (synonym Stagonospora nodorum (Stagonospora leaf blotch)); Uncinula necator (synonym Erysiphe necator) on vine (powdery mildew, anamorph: Oidium tuckeri); Setosphaeria species on maize (e.g., S. turcicum, synonym Helminthosporium turcicum) and turfgrass (leaf blight); maize (e.g., Sphacelotheca reiliana (Kühn) Clint.) andreiliana), synonym Ustilago reiliana: head smut), Sphacelotheca species on sorghum and sugarcane (smut); Sphaerotheca fuliginea on cucurbits (synonym Podosphaera xanthii: powdery mildew); Spongospora subterranea on potatoes (powdery scab) and virus diseases transmitted thereby; Stagonospora species on cereals, e.g., Stagonospora nodorum on wheat (Stagonospora leaf blotch, sexual form: Leptosphaeria nodorum [synonym Phaeosphaeria nodorum]), synonym Septoria nodorum); Synchytrium endobioticum on potatoes (potato wart disease); Taphrina species, e.g., 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), e.g., Thielaviopsis basicola (synonym Chalara elegans); Tilletia species on cereals (common bunt or stinking smut), e.g., Tilletia tritici on wheat (synonym Tilletia caries, common bunt of wheat) and Tilletia controversa (dwarf bunt); Trichoderma harzianum on mushrooms; Typhula incarnata on barley or wheat (grey snow mold); Urocystis species, e.g., Urocystis occulta on rye (stem smut); 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 UromycesSpecies of the genus Uromyces (rust) on fabae; species of the genus Ustilago (loose smut) on cereals (e.g., U. nuda and U. avenae on wheat, oats), maize (e.g., U. maydis: corn smut) and sugarcane; species of the genus Venturia (scab) on apples (e.g., V. inaequalis) and pears; and species of the genus Verticillium (wilt) on a variety of plants such as fruits and ornamental plants, vines, soft fruits, vegetables and field crops, e.g., V. longisporum on rape, V. dahliae on strawberries, rape, potatoes and tomatoes, and V. fungicola on mushrooms; Septoria tritici on cereals.

[0309] Compound I and its compositions are particularly suitable for controlling the pathogenic agents of the following plant diseases, respectively: 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, rape and sunflowers (e.g., Botrytis cinerea on strawberries and vines, Sclerotinia sclerotiorum, Sclerotinia minor and Sclerotium rolfsii on 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 the genus 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 the genus Cercospora on maize and soybeans).

[0310] According to one embodiment, compounds I.A-1.1a.B-1 to I.A-1.1a.B-180 are particularly suitable for controlling the pathogenic agents of the plant diseases according to list Z.

[0311] According to one embodiment, compounds I.A-2.1a.B-1 to I.A-2.1a.B-180 are particularly suitable for controlling the pathogenic agents of the plant diseases according to list Z.

[0312] According to one embodiment, compounds I.A-3.1a.B-1 to I.A-3.1a.B-180 are particularly suitable for controlling the pathogenic agents of the plant diseases according to list Z.

[0313] According to one embodiment, compounds I.A-4.1a.B-1 to I.A-4.1a.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-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.

[0315] 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.

[0316] 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.

[0317] 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.

[0318] 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.

[0319] 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.

[0320] 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.

[0321] 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.

[0322] 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.

[0323] 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.

[0324] 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.

[0325] 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.

[0326] 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.

[0327] 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.

[0328] 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.

[0329] 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.

[0330] 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.

[0331] 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.

[0332] 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.

[0333] 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.

[0334] 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.

[0335] 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.

[0336] 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.

[0337] 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.

[0338] 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.

[0339] 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.

[0340] 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.

[0341] 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.

[0342] 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.

[0343] 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.

[0344] 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.

[0345] 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.

[0346] 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.

[0347] 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.

[0348] 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.

[0349] 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.

[0350] 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.

[0351] 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.

[0352] 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.

[0353] List Z:

[0354] Species of the genus Albugo (white rust) on ornamental plants, vegetables (e.g., Albugo candida), and sunflowers (e.g., Albugo tragopogonis); species of the genus Alternaria (alternaria leaf spot) on vegetables (e.g., Alternaria dauci or Alternaria porri), 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 the genus Aphanomyces on sugar beet and vegetables; species of the genus 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 the genus Bipolaris and species of the genus Drechslera (sexual form: species of the genus 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 such as 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, rape, ornamental plants (e.g., Botrytis elliptica), vines, forest plants, and wheat; Bremia lactucae (downy mildew) on lettuce; species of the genus 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 leaf spot); Cladobotryum (synonym Dactylium) species on mushrooms (e.g., Cladobotryum mycophilum (formerly known as Dactylium dendroides), teleomorph: Nectria albertinii, Nectria rosella synonym Hypomyces rosellus); Cladosporium species on tomato (e.g., Cladosporium fulvum: leaf mold) and cereals, e.g., Cladosporium herbarum on wheat (black ear); Claviceps purpurea on cereals (ergot); Cochliobolus (anamorph: Helminthosporium of the genus Bipolaris) species on maize (Cochliobolus carbonum), cereals (e.g., Cochliobolus sativus, anamorph: Bipolaris sorokiniana) and rice (e.g., Cochliobolus miyabeanus, anamorph: Helminthosporium oryzae) (leaf spot); Colletotrichum on cotton (e.g., Colletotrichum gossypii), maize (e.g., Colletotrichum graminicola: anthracnose stalk rot), soft fruits, potato (e.g., Colletotrichum coccodes: black dot), common bean (e.g., Colletotrichum lindemuthianum), soybean (e.g., Colletotrichum truncatum or Colletotrichum gloeosporioides), vegetables (e.g., Colletotrichum lagenarium or Colletotrichum capsici), fruits (e.g., Colletotrichum acutatum), coffee (e.g., Colletotrichum coffeanum or Colletotrichum kahawae) and various crops (ColletotrichumSpecies of Colletotrichum (sexual stage: Glomerella) on gloeosporioides)) (anthracnose); species of Corticium, such as C. sasakii on rice (sheath blight); Corynespora cassiicola on soybean, cotton and ornamental plants (leaf spot); species of Cycloconium, such as C. oleaginum on olive; species of Cylindrocarpon on fruit trees, vines (e.g., C. liriodendri, sexual stage: Neonectria liriodendri: Black Foot Disease) and ornamental plants (e.g., fruit tree canker or young vine decline, sexual stage: species of Nectria or Neonectria); Dematophora necatrix on soybean (sexual stage: Rosellinia necatrix) (root and stem rot); species of Diaporthe, such as D. phaseolorum on soybean (damping-off); species of Drechslera (synonym Helminthosporium, sexual stage: Pyrenophora) on maize, 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; pear fruit (E. pyri), soft fruit (E.veneta): Elsinoe species on anthracnose and vines (Elsinoe ampelina: anthracnose); Entyloma oryzae on rice (leaf smut); Epicoccum species on wheat (black mold); Erysiphe species (powdery mildew) on sugar beet (Erysiphe betae), vegetables (e.g., Erysiphe pisi on peas) such as cucurbits (e.g., Erysiphe cichoracearum), cabbage, rapeseed (e.g., Erysiphe cruciferarum); Eutypa lata (Eutypa canker or dieback, anamorph: Cytosporina lata, synonym Libertella blepharis) on fruit trees, vines and ornamental woods; Exserohilum (synonym Helminthosporium) species on maize (e.g., Exserohilum turcicum); Fusarium (sexual form: Gibberella) species (wilt, root or stem rot) on various plants, 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; Gibberella species 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 cottonon gossypii); Grain staining complex on rice; Guignardia bidwellii (black rot) on vines; Gymnosporangium species on Rosaceae plants and junipers, such as Gymnosporangium sabinae (rust) on pears; Helminthosporium species (synonym Drechslera, teleomorph: Cochliobolus) on maize, cereals, potatoes and rice; Hemileia species, such as Hemileia vastatrix (coffee leaf rust) on coffee; 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 groundnuts, such as Mycosphaerella graminicola (anamorph: Zymoseptoria tritici, previously known as Septoria tritici: Septoria leaf blotch) on wheat, or Mycosphaerella fijiensis (synonym Pseudocercospora fijiensis: black Sigatoka disease) and Mycosphaerella musicola on bananas, Mycosphaerella arachidicola (synonym M.arachidis or Cercospora arachidis) on groundnuts, Mycosphaerella berkeleyi, Mycosphaerella pisi on peas and Mycosphaerella brassiciola on Brassica; on cabbages (e.g. PeronosporaSpecies of Peronospora (downy mildew) on Brassica species (e.g., Peronospora parasitica on Brassica oleracea), rape (e.g., Peronospora parasitica on Brassica napus), onion (e.g., Peronospora destructor on Allium cepa), tobacco (Peronospora tabacina on Nicotiana tabacum), and soybean (e.g., Peronospora manshurica on Glycine max); Phakopsora pachyrhizi and Phakopsora meibomiae on soybean (soybean rust); Species of Phialophora, such as on vines (e.g., Phialophora tracheiphila and Phialophora tetraspora) and soybean (e.g., Phialophora gregata on Glycine max: stem rot); Phoma lingam (synonyms Leptosphaeria biglobosa and Leptosphaeria 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; Species of Phomopsis on sunflower, vines (e.g., Phomopsis viticola on Vitis vinifera: cane and leaf spot) and soybean (e.g., Phomopsis phaseoli on Glycine max: stem rot, teleomorph: Diaporthe phaseolorum); Physoderma maydis on maize (brown spot); Species of Phytophthora (wilt, root, leaf, fruit, and stem rot) on various plants, such as red pepper and gourd (e.g., Phytophthora capsici), soybean (e.g., Phytophthora megasperma, synonym Phytophthora sojae), potato and tomato (e.g., Phytophthora infestans: late blight), and broadleaf trees (e.g., Phytophthora ramorum: sudden oak death); Plasmodiophora brassicae (club root) on cabbage, rape, radish, and other plants; Species of Plasmopara, such as Plasmopara viticola on vines (grapevine downy mildew) and Plasmopara halstedii on sunflower; Species of Podosphaera (powdery mildew) on Rosaceae plants, hops, pome fruits, and soft fruits, such as Podosphaera leucotricha on apple and Podosphaera xanthii on gourdPolymyxa species on, for example, cereals such as barley and wheat (P. graminis) and sugar beet (P. betae), and the 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, for example P. cubensis on cucurbits or P. humili on hops; Pseudopezicula tracheiphila (red fire disease or rotbrenner, anamorph: Phialophora) on vines; Puccinia species (rust) on various plants, for example P. triticina (brown rust or leaf rust), P. striiformis (stripe rust or yellow rust), P. hordei (dwarf rust), P. graminis (stem rust or black rust) or P. recondita (brown rust or leaf rust) on cereals such as wheat, barley or rye, P. kuehnii (citrus rust) on sugar cane and P. asparagi on asparagus; Pyrenopeziza species, for example P. brassicae on oilseed rape; Pyrenophora tritici-repentis (anamorph: Drechslera tritici-repentis) (tan spot) on wheat or P. teres (net blotch) on barley; Pyricularia species, for example P. oryzae (teleomorph: Magnaporthe grisea: rice blast) on rice, and P. grisea on turfgrass and cereals; Pythium species (damping-off) (for example P. ultimum or P. aphanidermatum) on turfgrass, rice, maize, wheat, cotton, oilseed rape, sunflower, soybean, sugar beet, vegetables and various other plants, and P. oligandrum on mushroomsoligandrum); Ramularia species, such as R. collo-cygni on barley (Ramularia leaf spot, physiological leaf spot), R. areola on cotton (teleomorph: Mycosphaerella areola) and R. beticola on sugar beet; Rhizoctonia species on cotton, rice, potato, turfgrass, maize, oilseed rape, potato, sugar beet, vegetables and many other plants, such as R. solani on soybean (root and stem rot), R. solani on rice (sheath blight) or R. cerealis on wheat or barley (Rhizoctonia spring leaf blight); Rhizopus stolonifer (black mold, soft rot) on strawberry, carrot, cabbage, vine and tomato; Rhynchosporium secalis and R. commune on barley, rye and triticale (scald); Sarocladium oryzae and S. attenuatum on rice (sheath rot); Sclerotinia species (stem rot or white mold) on vegetables (S. minor and S. sclerotiorum) and field crops, such as oilseed rape, sunflower (e.g. S. sclerotiorum) and soybean; Sclerotium rolfsii (synonym Athelia rolfsii) on soybean, peanut, vegetables, maize, cereals and ornamental plants; Septoria species on many plants, such as S. glycines on soybean (brown spot), S. tritici on wheat (synonym Zymoseptoria tritici, Septoria blotch) and S. nodorum on cereals (synonym Stagonospora nodorum (Stagonospora blotch)); Uncinula necator on vine (synonym Erysiphe necator) (powdery mildew, anamorph: Oidium tuckeri); Setosphaeria species on maize (e.g. S. turcicum, synonym Helminthosporium turcicum) and turfgrass (leaf blight); maize (e.g., Sphacelotheca reiliana (S.reiliana), synonym Ustilago reiliana: head smut), Sphacelotheca species on sorghum and sugarcane (smut); Sphaerotheca fuliginea on cucurbits (synonym Podosphaera xanthii: powdery mildew); Spongospora subterranea on potatoes (powdery scab) and virus diseases transmitted thereby; Stagonospora species on cereals, e.g., Stagonospora nodorum on wheat (Stagonospora leaf blotch, sexual form: Leptosphaeria nodorum [synonym Phaeosphaeria nodorum], synonym Septoria nodorum); Synchytrium endobioticum on potatoes (potato wart disease); Taphrina species, e.g., 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), e.g., Thielaviopsis basicola (synonym Chalara elegans); Tilletia species on cereals (common bunt or stinking smut), e.g., Tilletia tritici on wheat (synonym Tilletia caries, common bunt of wheat) and Tilletia controversa (dwarf bunt); Trichoderma harzianum on mushrooms; Typhula incarnata on barley or wheat (grey snow mold); Urocystis species, e.g., Urocystis occulta on rye (stem smut); 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 UromycesUromyces species (rust) on fabae); Ustilago species (loose smut) on cereals (e.g., U. nuda and U. avenae), maize (e.g., U. maydis: corn smut) and sugar cane; Venturia species (scab) on apples (e.g., V. inaequalis) and pears; and Verticillium species (wilt) on a variety of plants such as fruit and ornamental plants, vines, soft fruit, vegetables and field crops, e.g., V. longisporum on rape, V. dahliae on strawberries, rape, potatoes and tomatoes, and V. fungicola on mushrooms; Septoria tritici on cereals.

[0355] 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.

[0356] The term "stored product or harvested crop" 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, wetted, 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, the "stored product" 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.

[0357] 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.

[0358] 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.

[0359] Compound I and its compositions can be used respectively to improve the health of plants. The present invention also relates to a method for improving the health of plants by treating plants, their propagation materials, and / or the places where plants are growing or will grow with an effective amount of Compound I and its compositions respectively.

[0360] The term "plant health" should be understood to represent the condition of plants and / or their products, which is determined by a number of indicators, either alone or in combination with each other, such as yield (e.g., increased biomass and / or increased content of valuable components), plant vigor (e.g., improved plant growth and / or greener leaves ("greening effect")), quality (e.g., improved content or composition of certain components), and tolerance to abiotic and / or biotic stresses. The indicators of plant health status determined above can be interdependent or can influence each other.

[0361] Compound I is used as such or in the form of a composition to treat fungi, plants to be protected from fungal attack, plant propagation materials (such as seeds), soil, surfaces, materials, or rooms 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.

[0362] The agrochemical composition contains a fungicidally effective amount of Compound I. The term "fungicidally effective amount" means an amount of the composition or Compound I that is sufficient to control harmful fungi in the protection of cultivated plants, or stored products or harvested crops, or the protection of materials, and that does not cause substantial damage to the treated plants, treated stored products or harvested crops, or 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, harvested crops or materials to be treated, climatic conditions, and the specific Compound I used.

[0363] Plant propagation materials can be prophylactically treated with Compound I itself or a composition containing at least one Compound I at the time of planting or transplantation or before planting or transplantation.

[0364] 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.

[0365] In the treatment of plant propagation material (such as seeds), for example by dusting, coating or soaking, an amount of 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 is required per 100 kg of plant propagation material (preferably seeds).

[0366] The user generally applies the agrochemical composition by means of a pre-metering device, a knapsack sprayer, a spray tank, a spray aircraft, or an irrigation system. Generally, the agrochemical composition is made up with water, buffer solution, and / or other adjuvants to the desired application concentration, and thus a ready-to-use spray liquor 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 liquor are applied per hectare of agricultural useful area.

[0367] Compound I, its N-oxides and salts can be converted into agrochemical compositions of common types, 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, tablets, wettable powders or dusts (e.g., WP, SP, WS, DP, DS), tablets (e.g., BR, TB, DT), granules (e.g., WG, SG, GR, FG, GG, MG), insecticidal products (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 agrochemical compositions comprising adjuvants and at least one compound I.

[0368] Suitable adjuvants are solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, auxiliaries, solubilizers, penetration enhancers, protective colloids, adhesives, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, fungicides, antifreezes, antifoaming agents, colorants, tackifiers and binders.

[0369] Suitable solvents and liquid carriers are water and organic solvents such as medium to high boiling mineral oil fractions, e.g., kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cycloaliphatic 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.

[0370] Suitable solid carriers or fillers are mineral earths such as silicates, silica gel, talc, kaolin, limestone, lime, chalk, clay, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides such as cellulose, starch; fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea; products of vegetable origin such as cereal flour, bark powder, wood powder, nut shell powder and mixtures thereof.

[0371] 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).

[0372] 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, dodecylbenzene and tridecylbenzene sulfonates, naphthalene and alkylnaphthalene sulfonates, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids, oils, ethoxylated alkylphenols, alcohols, ethoxylated alcohols or fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates and carboxylated alcohol or alkylphenol ethoxylates.

[0373] Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based 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 by 1 to 50 equivalents. Oxyethylene 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, glycerides or monoglycerides. Examples of sugar-based surfactants are sorbitan, ethoxylated sorbitan, sucrose and glucose esters or alkyl polyglucosides. Examples of polymeric surfactants are homologues or copolymers of vinyl pyrrolidone, vinyl alcohol or vinyl acetate.

[0374] Suitable cationic surfactants are quaternary ammonium surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups or salts of long chain primary amines. Suitable amphoteric surfactants are alkyl betaines and imidazolines. Suitable block polymers are AB or ABA type block polymers comprising polyethylene oxide and polypropylene oxide blocks, or ABC type block polymers comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. The example of polyacids is an alkali metal salt of polyacrylic acid or a polyacid comb-like polymer. The example of a polybasic base is polyvinylamine or polyvinylamine.

[0375] Suitable adjuvants are compounds which themselves have negligible or even no pesticidal activity and which improve the biological performance of compound I against the target. Examples are surfactants, mineral 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.

[0376] Suitable thickeners are polysaccharides (eg xanthan gum, carboxymethylcellulose), inorganic clays (organically modified or unmodified), polycarboxylates and silicates.

[0377] Suitable fungicides are bronopol and isothiazolinone derivatives, such as alkylisothiazolinones and benzisothiazolinones.

[0378] Suitable antifreeze agents are ethylene glycol, propylene glycol, urea and glycerol.

[0379] Suitable defoamers are silicones, long-chain alcohols and salts of fatty acids.

[0380] Suitable colorants (e.g., red, blue or green) are low 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).

[0381] Suitable thickeners or binders are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, polyacrylate, biological wax or synthetic wax, and cellulose ether.

[0382] 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% of an active substance (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% of at least one auxiliary agent. The active substance (such as compound I) is used in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectra).

[0383] For the purpose of treating plant propagation materials, especially seeds, solutions for seed treatment (LS), suspension emulsions (SE), flowable concentrates (FS), powders for dry treatment (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 substance in the ready-to-use preparation of the composition in question is from 0.01% to 60% by weight, preferably 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 materials, especially seeds, respectively, include dressing, coating, granulation, dusting, soaking and in-furrow application methods. Preferably, compound I or its composition is applied to plant propagation materials separately by a method that does not induce germination, such as by dressing, granulation, coating and dusting.

[0384] Various types of oils, wetting agents, adjuvants, fertilizers or micronutrients, and additional pest control agents (such as fungicides, growth regulators, herbicides, insecticides, safeners) can be added to compound I or its composition as a premix, or added only until immediately before 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.

[0385] A pesticidal agent is generally a chemical or biological agent (such as a pesticidal active ingredient, compound, composition, virus, bacterium, antimicrobial agent 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 "pesticidal agent" 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 off 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 pesticidal agents 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.

[0386] Biopesticidal agents 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 / ). Biopesticidal agents fall into two main categories, microbial and biochemical pesticidal agents:

[0387] (1) Microbial pesticidal agents consist of bacteria, fungi or viruses (and usually include metabolites produced by bacteria and fungi). Entomopathogenic nematodes are also classified as microbial pesticidal agents, although they are multicellular.

[0388] (2) Biochemical pesticidal agents are naturally occurring substances that control pests or provide other crop protection uses as defined below, but are relatively non-toxic to mammals.

[0389] Mixing compound I or a composition containing them, in the form of a fungicidal use, 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.

[0390] The following list of pesticidal agents II that can be used in combination with compound I is intended to illustrate possible combinations but does not limit them:

[0391] A) A) Respiratory inhibitors

[0392] - At Q o Complex III inhibitors at the Q-site: azoxystrobin (A.1.1), cacoxystrobin (A.1.2), coumoxystrobin (A.1.3), dimoxystrobin (A.1.4), enestroburin (A.1.5), enaminostrobin (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), famoxadone (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), pyridaben (A.1.36), picarbutrazox (A.1.37), 2-(o-((2,5-dimethylphenyl-oxymethylene)phenyl)-3-methoxy-acrylic acid methyl ester (A.1.38);

[0393] - At Q i Complex III inhibitors at the Q-site: cyazofamid (A.2.1), indaziflam (A.2.2), [(6S,7R,8R)-8-benzyl-3-[(3-hydroxy-4-methoxypyridine-2-carbonyl)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);

[0394] - Complex II inhibitors: carboxin (A.3.1), bixafen (A.3.2), boscalid (A.3.3), boscalid (A.3.4), oxycarboxin (A.3.5), furametpyr (A.3.6), fluxapyroxad (A.3.7), flutolanil (A.3.8), fluopyram (A.3.9), furpicoxamid (A.3.10), isofetamid (A.3.11), sedaxane (A.3.12), dimethomorph (A.3.13), oxycarboxin oxide (A.3.14), fluazaindolizine (A.3.15), pydiflumetofen (A.3.16), fluxametamide (A.3.17), bixafen (A.3.18), fluxapyrad (A.3.19), tetcyclacis (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)nicotinamide (A.3.32), 2-(difluoromethyl)-N-[(3R)-1,1,3-trimethylinden-4-yl]nicotinamide (A.3.33), 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethylinden-4-yl)nicotinamide (A.3.34), 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethylinden-4-yl]nicotinamide (A.3.35), 2-(difluoromethyl)-N-(1,1-dimethyl-3-propylinden-4-yl)nicotinamide (A.3.36), 2-(difluoromethyl)-N-[(3R)-1,1-dimethyl-3-propylinden-4-yl]nicotinamide (A.3.37), 2-(difluoromethyl)-N-(3-isobutyl-1,1-dimethylinden-4-yl)nicotinamide (A.3.38), 2-(difluoromethyl)-N-[(3R)-3-isobutyl-1,1-dimethylinden-4-yl]nicotinamide (A.3.39), fluazinam (A.3.24);

[0395] - Other respiratory inhibitors: difluralin (A.4.1); nitro-phenyl derivatives: binapacryl (A.4.2), dinobuton (A.4.3), dinocap (A.4.4), fluazinam (A.4.5), dicofol (A.4.6), ferimzone (A.4.7); organo-metallic compounds: triphenyltin salts, e.g., triphenyltin acetate (A.4.8), triphenyltin chloride (A.4.9) or triphenyltin hydroxide (A.4.10); amisulbrom (A.4.11); silthiofam (A.4.12);

[0396] B) Sterol biosynthesis inhibitors (SBI fungicides)

[0397] -C14 demethylase inhibitors: Triazoles: penconazole (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), pefurazoate (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), triticonazole (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), fluxapyroxad (B.1.33), ipfentrifluconazole (B.1.37), metconazole (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-tolylmethyl)-1-(1,2,4-triazol-1-ylmethyl)cyclopentanol (B.1.43); Imidazoles: imazalil (B.1.44), fenarimol (B.1.45), prochloraz (B.1.46), triflumizole (B.1.47); Pyrimidines, pyridines, piperazines: chlorfenapyr (B.1.49), pyrifenox (B.1.50), tridemorph (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), methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propionate (B.1.56), 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoic acid (B.1.57);

[0398] -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), quinomethionate (B.2.5), fenpropidin (B.2.6), tridemorph (B.2.7), spiroxamine (B.2.8);

[0399] -3-ketoreductase inhibitors: fenhexamid (B.3.1);

[0400] -other sterol biosynthesis inhibitors: etaconazole (B.4.1);

[0401] C) Nucleic acid synthesis inhibitors

[0402] -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), ofurace (C.1.6), oxadixyl (C.1.7);

[0403] -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);

[0404] D) Cell division and cytoskeleton inhibitors

[0405] - 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);

[0406] - 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), phenamacril (D.2.8);

[0407] E) Amino acid and protein synthesis inhibitors

[0408] - Methionine synthesis inhibitors: cyprodinil (E.1.1), fenarimol (E.1.2), pyrimethanil (E.1.3);

[0409] - Protein synthesis inhibitors: blasticidin-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);

[0410] F) Signal transduction inhibitors

[0411] - MAP / Histidine Kinase Inhibitors: fluoroimid (F.1.1), iprodione (F.1.2), procymidone (F.1.3), vinclozolin (F.1.4), fludioxonil (F.1.5);

[0412] - G-Protein Inhibitors: quinoxyfen (F.2.1);

[0413] G) Lipid and Membrane Synthesis Inhibitors

[0414] - Phospholipid Biosynthesis Inhibitors: edifenphos (G.1.1), isoprothiolane (G.1.2), pyrazophos (G.1.3), isoprobenfos (G.1.4);

[0415] - 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);

[0416] - Phospholipid Biosynthesis and Cell Wall Deposition: dimethomorph (G.3.1), flumorph (G.3.2), mandipropamid (G.3.3), pyrimorph (G.3.4), benthiavalicarb (G.3.5), iprovalicarb (G.3.6), valifenalate (G.3.7);

[0417] - Compounds Affecting Cell Membrane Permeability and Fatty Acids: propamocarb (G.4.1);

[0418] Oxysterol-binding protein inhibitors: flutianil (G.5.1), fluoxapiprolin (G.5.3), 4-[1-[2-[3-difluoromethyl-5-methyl-pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphthalen-1-yl-pyridine-2-carboxamide (G.5.4), 4-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphthalen-1-yl-pyridine-2-carboxamide (G.5.5), 4-[1-[2-[3-(difluoromethyl)-5-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphthalen-1-yl-pyridine-2-carboxamide (G.5.6), 4-[1-[2-[5-cyclopropyl-3-(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphthalen-1-yl-pyridine-2-carboxamide (G.5.7), 4-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphthalen-1-yl-pyridine-2-carboxamide (G.5.8), 4-[1-[2-[5-(difluoromethyl)-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphthalen-1-yl-pyridine-2-carboxamide (G.5.9), 4-[1-[2-[3,5-bis(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphthalen-1-yl-pyridine-2-carboxamide (G.5.10), (4-[1-[2-[5-cyclopropyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphthalen-1-yl-pyridine-2-carboxamide (G.5.11);

[0419] H) Inhibitors with multi-site action

[0420] - 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);

[0421] - Thio- and dithiocarbamates: ferric dimethyldithiocarbamate (H.2.1), mancozeb (H.2.2), maneb (H.2.3), metam-sodium (H.2.4), metiram (H.2.5), zinc methyl dithiocarbamate (H.2.6), thiram (H.2.7), zinc dithiocarbamate (H.2.8), zinc dimethyldithiocarbamate (H.2.9);

[0422] - 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);

[0423] - 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-triacetate (H.4.7), guazatine-tris (octylphenylsulfonate) (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);

[0424] I) Cell wall synthesis inhibitors

[0425] - Glucan synthesis inhibitors: validamycin (I.1.1), polyoxin (I.1.2);

[0426] - Melanin synthesis inhibitors: pyroquilon (I.2.1), tricyclazole (I.2.2), carpropamid (I.2.3), dicyclomet (I.2.4), blastoxamide (I.2.5);

[0427] J) Plant defense inducers

[0428] - Benzo-S-methyl alaninate (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);

[0429] K) Unknown mode of action

[0430] -Bronopol (K.1.1), Chinomethionat (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 chrysanthemumate (K.1.12), Amibenapyrone (K.1.13), Flumetover (K.1.14), Flumetylsulforim (K.1.60), Sulfuramide (K.1.15), Flutianil (K.1.16), Harpin protein (K.1.17), Sulfosultap (K.1.18), 3,5,6 - Trichloro - 2 - picoline (K.1.19), Phthalide (K.1.20), Tolprocarb (K.1.21), Copper quinolate (K.1.22), Propoxyquinoline (K.1.23), Seboctylamine (K.1.61), Tebufloquin (K.1.24), Phyllachlor (K.1.25), Azoxystrobin (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-dimethylisoxazolidin-3-yl]pyridine (picoxystrobin) (K.1.37), 3-[5-(4-methylphenyl)-2,3-dimethylisoxazolidin-3-yl]pyridine (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-phenylprop-2-enoate (K.1.40), tetraconazole (K.1.41), N-[6-[[(Z)-[(1-methyltetrazol-5-yl)phenylmethylene]amino]oxymethyl]-2-pyridyl]pentylcarbamate (K.1.42), N-[6-[[(Z)-[(1-methyltetrazol-5-yl)phenylmethylene]amino]oxymethyl]-2-pyridyl]but-3-ynylcarbamate (K.1.43), ipflufenoquin (K.1.44), quinofumelin (K.1.47), beaucvericin (K.1.48), bromothalonil (K.1.49), 2-(6-benzyl-2-pyridyl)quinazoline (K.1.50), 2-[6-(3-fluoro-4-methoxyphenyl)-5-methyl-2-pyridyl]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), fluxapyroxad (K.1.55), N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxyethoxy)-3-pyridyl]-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), flufenoxadiazam (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 (K.1.60; WO 2018 / 177894, WO 2020 / 212513), N-((4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl)methyl)propanamide (K.1.62), 3,3,3-trifluoro-N-[[3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide (K.1.63), 3,3,3-trifluoro-N-[[2-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide (K.1.64), N-[2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl]butanamide (K.1.65), N-[[2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-3,3,3-trifluoro-propanamide (K.1.66), 1-methoxy-1-methyl-3-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea (K.1.67), 1,1-diethyl-3-[[4-[5-[trifluoromethyl]-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea (K.1.68), N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide (K.1.69), N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide (K.1.70), 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea (K.1.71), 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one (K.1.72), 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one (K.1.73), 4-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]morpholin-3-one (K.1.74), 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one (K.1.75), 2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one (K.1.76), 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one (K.1.77), 3,3-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one (K.1.78), 2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]oxazinan-3-one (K.1.79), 1-[[3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]azepan-2-one (K.1.80), 4,4-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one (K.1.81), 5-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one (K.1.82), ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylate (K.1.83), N-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxamide (K.1.84), N,N-dimethyl-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl]-1H-1,2,4-triazol-3-amine (K.1.85), N-methoxy-N-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxamide (K.1.86), propyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxamide (K.1.87), N-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxamide (K.1.88), N-allyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide (K.1.89), 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea (K.1.90), 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea (K.1.91), N-allyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]acetamide (K.1.92), N-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl]cyclopropanecarboxamide (K.1.93), 1-methyl-3-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea (K.1.94), N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylformamidine (K.1.95), N'-[2-chloro-4-[(4-methoxyphenyl)methyl]-5-methylphenyl]-N-ethyl-N-methylformamidine (K.1.96), N'-[2-chloro-4-[(4-cyanophenyl)methyl]-5-methylphenyl]-N-ethyl-N-methylformamidine (K.1.97), N'-[2,5-dimethyl-4-(o-tolylmethyl)phenyl]-N-ethyl-N-methylformamidine (K.1.98), 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-N-[2-(2,4-dimethyl-phenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide (K.1.99), 3-(3-bromo-2-fluoro-phenoxy)-6-chloro-N-[2-(2-chloro-4-methyl-phenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide (K.1.100), 6-chloro-N-[2-(2-chloro-4-methyl-phenyl)-2,2-difluoro-ethyl]-3-(3-cyclopropyl-2-fluoro-phenoxy)-5-methyl-pyridazine-4-carboxamide (K.1.101), 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-N-[2-(3,4-dimethyl-phenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide (K.1.102), 6-chloro-3-(3-chloro-2-fluoro-phenoxy)-N-[2-(2,4-dimethyl-phenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide (K.1.103), N-[2-(2-bromo-4-methyl-phenyl)-2,2-difluoro-ethyl]-6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-5-methyl-pyridazine-4-carboxamide (K.1.104);.

[0431] L) Biopesticides

[0432] 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, Cryptosporiopsis parasiticola, 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 ochracea, 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 violaceusniger, Talaromyces flavus, Trichoderma asperelloides, Trichoderma asperellum, Trichoderma atroviride, Trichoderma apical, Trichoderma gamosum, Trichoderma harzianum, Trichoderma harmatum, Trichoderma polysporum, Trichoderma stromaticum, Trichoderma virens, Trichoderma viride, Typhula phacorrhiza, Ulocladium oudemansii, Verticillium dahliae, Zucchini yellow mosaic virus (avirulent strain);

[0433] L2) Biochemical pest control agents with fungicidal, bactericidal, virucidal and / or plant defense activator activities: harpin proteins, Reynoutria japonica Houtt. extract;

[0434] L3) Microbial pest control 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), Heliothis zea nucleopolyhedrovirus (HzNPV), Heliothis 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 penetrans, Pasteuria ramosa, Pasteuria thornei, Pasteuria usgae, Pseudomonas fluorescens, Spodoptera litura nucleopolyhedrovirus (SpliNPV), Steinernema carpocapsae, Steinernema feltiae, Steinernema sawfly, Streptomyces gilvosporeus, Streptomyces microflavus;

[0435] L4) Biochemical pesticides with insecticidal, acaricidal, molluscicidal, pheromonal and / or nematicidal activity: L-carvone, citral, (E,Z)-7,9-dodecadien-1-yl acetate, ethyl formate, (E,Z)-ethyl 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-tetradecatrien-1-yl 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;

[0436] L5) Microbial pesticides 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 viciae, Rhizobium leguminosarum biovar trifolii, Rhizobium leguminosarum biovar viceae, Rhizobium tropici, Sinorhizobium meliloti;

[0437] O) Insecticides from classes O.1 to O.29

[0438] O.1 Acetylcholinesterase (AChE) inhibitors: aldicarb, alanycarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, propoxur, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, XMC, xylylcarb, triazamate; acephate, azamethiphos, coumaphos, crotoxyphos, cyanophos, dichlorvos / DDVP, dimethoate, ethion, EPN, ethoprophos, fenamiphos, fenthion, fosthiazate, heptenophos, imicyafos, isopropylamine phosphate, isopropyl O-(methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, pyrethrins, pyriproxyfen, pyridaphenthion, quinalphos, sulprofos, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, vamidothion;

[0439] O.2 GABA-gated chloride channel antagonists: endosulfan, chlordane; ethiprole, fipronil, ethiprole, pyrafluprole, pyriprole;

[0440] O.3 Sodium channel modulators: acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, k-bifenthrin, bioallethrin, bioallethrin S-cyclopentyl, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flubrocythrinate, tau-fluvalinate, flumethrin, heptaflumethrin, imiprothrin, metofluthrin, metofluthrin, epsilon-metofluthrin, permethrin, phenothrin, propargite, profluthrin, pyrethrins (pyrethrum), resmethrin, silafluofen, heptafluthrin, k-heptafluthrin, tetraflumethrin, tetramethrin, tralomethrin, tetrachlorvinphos; DDT, methoxychlor;

[0441] 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-pentylideneamino guanidine; 1-[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridine; nicotine; sulfoxaflor, flupyradifurone, triflumezopyrim, bixafen, flufenerim;

[0442] O.5 Allosteric activators of nicotinic acetylcholine receptors: spinosad, spinetoram;

[0443] O.6 Chloride channel activators: abamectin, emamectin benzoate, ivermectin, lepimectin, milbemectin;

[0444] O.7 Juvenile hormone mimics: hydroprene, kinoprene, methoprene; fenoxycarb, pyriproxyfen;

[0445] O.8 Various non-specific (multisite) inhibitors: methyl bromide and other alkyl halides; chloropicrin, sulfuryl fluoride, borax, tartar emetic;

[0446] O.9 Chordotonal organ TRPV channel modulators: cyenopyrafen, pymetrozine, flonicamid;

[0447] O.10 Mite growth inhibitors: clofentezine, hexythiazox, flufenzine; etoxazole;

[0448] O.11 Microbial disruptors of the insect midgut membrane: Bacillus thuringiensis, Bacillus sphaericus and the insecticidal proteins they produce: Bacillus thuringiensis subsp. israelensis, Bacillus sphaericus, Bacillus thuringiensis subsp. aizawai, Bacillus thuringiensis subsp. kurstaki, Bacillus thuringiensis subsp. tenebrionis, Bt crop proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34 / 35Ab1;

[0449] O.12 Mitochondrial ATP synthase inhibitors: diafenthiuron; azocyclotin, cyhexatin, fenbutatin oxide, propargite, chlorfenson;

[0450] O.13 Oxidative phosphorylation uncouplers interfering via proton gradient: chlorfenapyr, DNOC, sulfluramid;

[0451] O.14 Nicotinic acetylcholine receptor (nAChR) channel blockers: bensultap, cartap, thiocyclam, bisultap;

[0452] O.15 Chitin biosynthesis inhibitor type 0: bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, chlorbenzuron, teflubenzuron;

[0453] O.16 Chitin biosynthesis inhibitor type 1: buprofezin;

[0454] O.17 Molting disruptors: cyromazine;

[0455] O.18 Ecdysone receptor agonists: methoxyfenozide, tebufenozide, chlorfenozide, furanfenozide, chromafenozide;

[0456] O.19 Octopamine receptor agonists: amitraz;

[0457] O.20 Mitochondrial complex III electron transport inhibitors: hydramethylnon, acequinocyl, fluacrypyrim, bifenazate;

[0458] O.21 Mitochondrial complex I electron transport inhibitors: fenazaquin, metofluthrin, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad; rotenone;

[0459] 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, N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide, 2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]hydrazinecarboxamide;

[0460] O.23 Acetyl-CoA carboxylase inhibitors: spirodiclofen, spiromesifen, spirotetramat, methoprene, spirodiclofen, 11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxo-9-aza-dispiro[4.2.4.2]tetradec-11-ene-10-one, dispirotetramat;

[0461] O.24 Mitochondrial complex IV electron transport inhibitors: aluminium phosphide, calcium phosphide, phosphine, zinc phosphide, cyanide;

[0462] O.25 Mitochondrial complex II electron transport inhibitors: cyenopyrafen, butylpyridaben, etoxazole, pyraclostrobin;

[0463] O.28 Ryanodine receptor modulators: chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubendiamide, flubendiamide, (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-[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; tetraniliprole; thiodicarb; N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloropyridin-2-yl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide; chlorantraniliprole; 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;

[0464] O.29 Chordotonal organ modulator: flonicamid;

[0465] O.30 GABA-gated chloride channel allosteric modulators: broflanilide, chlorantraniliprole, isoxazolinonitrile;

[0466] O.33 Calcium-activated potassium channel modulator: acynonapyr;

[0467] O.34 Mitochondrial complex III electron transport inhibitor at the Qi site: flometoquin;

[0468] O.UN Insecticidal compounds with unknown or uncertain mode of action: afoxolaner, azadirachtin, amidoflumet, bromopropylate, chlorbenside, chinomethionat, cryolite, cyproflanilid, dichlorothymid, dicofol, flupyradifurone, flonicamid, flometoquin, flupyradifurone, fluhexafon, fluxapyroxad, fluralaner, metaldehyde, oxydemethon-methyl, pyridalyl, piperonyl butoxide, pyridalyl, tioxazafen, trifluenfuronate, umifoxolaner, 11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxo-9-aza-dispiro[4.2.4.2]tetradec-11-en-10-one, 3-(4'-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]decan-3-en-2-one, 4-cyano-N-[2-cyano-5-[[[2,6-dibromo-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]amino]carbonyl]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]amino]carbonyl]-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]amino]carbonyl]-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]amino]carbonyl]-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]amino]carbonyl]phenyl]-2-methyl-benzamide, 1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1H-1,2,4-triazol-5-amine, N-[5-[[[2-bromo-6-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]amino]carbonyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide, 4-cyano-N-[2-cyano-5-[[[2,6-dichloro-4-[1,2,2,2-Tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]amino]carbonyl]phenyl]-2-methyl-benzamide, active substance based on Bacillus firmus (Votivo, I-1582); triflumizole; 5-[3-[2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1H-pyrazole; 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]-pyridine; 2-[6-[2-(5-fluoro-3-pyridyl)-5-thiazolyl]-2-pyridyl]-pyrimidine; 2-[6-[2-(3-pyridyl)-5-thiazolyl]-2-pyridyl]-pyrimidine; N-methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide; N-methylsulfonyl-6-[2-(3-pyridyl)thiazol-5-yl]pyridine-2-carboxamide; 1-[(6-chloro-3-pyridyl)methyl]-1,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitro-imidazo[1,2-a]pyridine; 1-[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridin-5-ol; N-(3-chloro-2-methylphenyl)-2-[(4-chlorophenyl)[4-[methyl(methylsulfonyl)amino]phenyl]methylene]-hydrazinecarboxamide; 1-[(6-chloro-3-pyridyl)methyl]-1,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitro-imidazo[1,2-a]pyridine; 2-(3-pyridyl)-N-(2-pyrimidinylmethyl)-2H-indazole-5-carboxamide; chlorantraniliprole; 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; N-[4-chloro-3-[[(phenylmethyl)amino]carbonyl]phenyl]-1-methyl-3-(1,1,2,2-(2,2,2-pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide; 2-(3-ethylsulfonyl-2-pyridyl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-[3-ethylsulfonyl-5-(trifluoromethyl)-2-pyridyl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine; 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; benzpyrimoxan; tigolaner; oxasulfuron; [(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-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]methylidenehydrazino]thiazolidin-4-one, (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, (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]Pyridine, 2-(6-bromo-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-(3-ethylsulfonyl-6-iodo-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-(7-chloro-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-(7-chloro-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-(3-ethylsulfonyl-7-iodo-imidazo[1,2-a]pyridin-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 3-ethylsulfonyl-6-iodo-2-[3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridin-2-yl]imidazo[1,2-a]pyridine-8-carbonitrile, 2-[3-ethylsulfonyl-8-fluoro-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-[3-ethylsulfonyl-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethylsulfinyl)imidazo[4,5-b]pyridine, 2-[3-ethylsulfonyl-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine, 2-(6-bromo-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-6-(trifluoromethyl)pyrazolo[4,3-c]pyridine; N-[[2-fluoro-4-[(2S,3S)-2-hydroxy-3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]phenyl]methyl]cyclopropanecarboxamide; 2-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfinyl)phenyl]imino-3-(2,2,2-trifluoroethyl)thiazolidin-4-one; Fluvalinate, N-[3-chloro-1-(3-pyridinyl)pyrazol-4-yl]-2-methylsulfonyl-propionamide, Triflumizole; N-[4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl]-2-methyl-4-methylsulfonyl-5-(1,1,2,2,2-pentafluoroethyl)pyrazole-3-carboxamide, Cyflumetofen, Chlorantraniliprole; 1,4-dimethyl-2-[2-(pyridin-3-yl)-2H-indazol-5-yl]-1,2,4-triazolidine-3,5-dione, 2-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl]imino-3-(2,2,(2-trifluoroethyl)thiazolidin-4-one, indoxacarb, N-[4-chloro-2-(3-pyridyl)thiazol-5-yl]-N-ethyl-3-methylsulfonyl-propanamide, N-cyclopropyl-5-[(5S)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]isoquinoline-8-carboxamide, 5-[(5S)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]-N-(pyrimidin-2-ylmethyl)isoquinoline-8-carboxamide, N-[1-(2,6-difluorophenyl)pyrazol-3-yl]-2-(trifluoromethyl)benzamide, 5-((1R,3R)-3-(3,5-bis(trifluoromethyl)phenyl)-2,2-dichlorocyclopropane-1-carboxamido)-2-chloro-N-(3-(2,2-difluoroacetamido)-2,4-difluorophenyl)benzamide, 1-[6-(2,2-difluoro-7-methyl-[1,3]dioxolo[4,5-f]benzimidazol-6-yl)-5-ethylsulfonyl-3-pyridyl]cyclopropanecarbonitrile, 6-(5-cyclopropyl-3-ethylsulfonyl-2-pyridyl)-2,2-difluoro-7-methyl-[1,3]dioxolo[4,5-f]benzimidazole.,

[0469] 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 Numbers, which are 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.;

[0470] According to the present invention, the solid material (dry matter) of a biopesticide (except for oils such as neem oil, etc.) is considered to be the active ingredient (obtained, for example, in the case of a liquid formulation of a microbial pesticide after drying or evaporating 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.

[0471] 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.

[0472] In a binary mixture, the weight ratio of component 1) to component 2) generally depends on the properties of the components used and is usually in the range of 1:10,000 to 10,000:1, often in the range of 1:100 to 100:1, frequently in the range of 1:50 to 50:1, preferably in the range of 1:20 to 20:1, more preferably in the range of 1:10 to 10:1, even more preferably in the range of 1:4 to 4:1, and especially in the range of 1:2 to 2:1. According to another embodiment, the weight ratio of component 1) to component 2) is generally in the range of 1000:1 to 1:1, often in the range of 100:1 to 1:1, frequently in the range of 50:1 to 1:1, preferably in the range of 20:1 to 1:1, more preferably in the range of 10:1 to 1:1, even more preferably in the range of 4:1 to 1:1, and especially in the range of 2:1 to 1:1. According to another embodiment, the weight ratio of component 1) to component 2) is generally in the range of 20,000:1 to 1:10, often in the range of 10,000:1 to 1:1, frequently in the range of 5,000:1 to 5:1, preferably in the range of 5,000:1 to 10:1, more preferably in the range of 2,000:1 to 30:1, even more preferably in the range of 2,000:1 to 100:1, and especially in the range of 1,000:1 to 100:1. According to another embodiment, the weight ratio of component 1) to component 2) is generally in the range of 1:1 to 1:1000, often in the range of 1:1 to 1:100, frequently in the range of 1:1 to 1:50, preferably in the range of 1:1 to 1:20, more preferably in the range of 1:1 to 1:10, even more preferably in the range of 1:1 to 1:4, and especially in the range of 1:1 to 1:2. According to another embodiment, the weight ratio of component 1) to component 2) is generally in the range of 10:1 to 1:20,000, often in the range of 1:1 to 1:10,000, frequently in the range of 1:5 to 1:5,000, preferably in the range of 1:10 to 1:5,000, more preferably in the range of 1:30 to 1:2,000, even more preferably in the range of 1:100 to 1:2,000, and especially in the range of 1:100 to 1:1,000.

[0473] 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 usually in the range of 1:100 to 100:1, frequently in the range of 1:50 to 50:1, preferably in the range of 1:20 to 20:1, more preferably in the range of 1:10 to 10:1, and especially in the range of 1:4 to 4:1, and the weight ratio of component 1) to component 3) is usually in the range of 1:100 to 100:1, frequently in the range of 1:50 to 50:1, preferably in the range of 1:20 to 20:1, more preferably in the range of 1:10 to 10:1, and especially in the range of 1:4 to 4:1. If desired, any additional active components are added to component 1) in a ratio of 20:1 to 1:20. These ratios are also suitable for mixtures applied by seed treatment.

[0474] When a mixture containing a microbial pestcide is used for crop protection, the application rate ranges from 1×10 6 to 5×10 16 (or greater) 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 pestcides (e.g., Steinernema feltiae), the application rate range is often from 1×10 5 to 1×10 12 (or greater), 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.

[0475] When a mixture containing a microbial pestcide is used for seed treatment, the application rate range is generally from 1×10 6 to 1×10 12 (or greater) 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 greater) CFU / 100 kg of seeds, preferably from 1×10 9 to 1×10 12 CFU / 100 kg of seeds.

[0476] 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).

[0477] Also preferred is a mixture comprising at least one active substance as component 2), the at least one active substance being selected from the complex III inhibitors in 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).

[0478] Also preferred is a mixture comprising at least one active substance as component 2), the at least one active substance being selected from the complex II inhibitors in 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).

[0479] 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).

[0480] 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); in particular 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).

[0481] 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).

[0482] 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); in particular selected from (C.1.1) and (C.1.4).

[0483] 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).

[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 D), more preferably selected from 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).

[0485] 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 compounds (E.1.1), (E.1.3), (E.2.2) and (E.2.3); particularly (E.1.3).

[0486] 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 compounds (F.1.2), (F.1.4) and (F.1.5).

[0487] 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 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).

[0488] 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 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).

[0489] 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 compounds (I.2.2) and (I.2.5).

[0490] 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 compounds (J.1.2), (J.1.5), (J.1.8), (J.1.11) and (J.1.12); particularly (J.1.5).

[0491] Also preferably included is a mixture of at least one active substance as component 2), the at least one active substance being 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).

[0492] 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.

[0493] Microbial biopesticides, particularly 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.

[0494] 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: A mixture of Aureobasidium pullulans DSM14940 and DSM 14941 was isolated in Konstanz, Germany in 1989 (e.g., blastospores, from ) Bio-Ferm GmbH, Austria), Azospirillum brasilense Sp245 was initially isolated at least before 1980 in the wheat-growing region 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., Quartelúbalas, Brazil, or from Simbiose-Agro, Brazil 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 referred to as Bacillus subtilis, recently reclassified as Bacillus velezensis together with Bacillus methylotrophicus and 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 ) 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., from 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 ) 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., from 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) isolated in 1992 in 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 GHA180 isolated from the rhizosphere of apple trees 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 cucumbers infected with Erwinia tracheiphila (NRRL B-50185, NRRL B-50153; US 8,445,255), Bacillus pumilus KFP9F isolated from the rhizosphere of grass in South Africa at least prior to 2008 (NRRL B-50754; WO 2014 / 029697; e.g., BAC-UP or FUSION-P from BASF Agricultural Specialities (Pty) Ltd., South Africa), Bacillus pumilus QST2808 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 beet root in North America (ATCC PTA-11857; System Appl Microbiol [System and Applied Microbiology] 27, 372-379, 2004; US2010 / 0260735; WO2011 / 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, Menzingen, Germany of ), Bacillus thuringiensis subsp. kurstaki ABTS-351 is equivalent to HD-1 isolated in 1967 from diseased black larvae of the cotton bollworm in Brownsville, Texas, USA (ATCC SD-1275; e.g., from Valent BioSciences, Illinois, USA of DF), Bacillus thuringiensis subsp. kurstaki SB4 was isolated from the larval cadavers of the African sugarcane borer (E. saccharina) (NRRL B-50753; e.g., from BASF Agricultural Specialities (Pty) Ltd., South Africa of ), Bacillus thuringiensis subsp. tenebrionis NB-176-1, a mutant of strain NB-125, was isolated from the dead pupae of the beetle Tenebrio molitor in 1982 (DSM 5480; EP 585 215B1; e.g., from Valent BioSciences, Switzerland of ), Beauveria bassiana GHA (ATCC 74250; e.g., from Laverlam Int. Corp., USA of 22WGP), Beauveria bassiana JW-1 (ATCC 74040; e.g., from CBC (Europe) S.r.l., Italy of ), Beauveria bassiana PPRI 5339 was isolated from the larvae of the tortoise beetle Conchyloctenia punctata (NRRL 50757; e.g., from BASF Agricultural Specialities (Pty) Ltd., South Africa of ),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; for example, GELFIX 5 from BASF Agricultural Specialties Ltd., Brazil), and 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; for example, (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 ADHERE 60 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 (CPAC 7; 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 (NRRL B-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 [Biocontrol Science and Technology]. 22(7), 747 - 761, 2012; e.g., PFR-97 from Certis LLC, USA TM 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 central 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), and 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 originally 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), Trichoderma asperellum JM41R isolated in South Africa (NRRL 50759; also known as Trichoderma viride; 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 ).

[0495] According to another embodiment of the mixture, at least one pesticidal agent II is selected from groups L1) to L5):

[0496] 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 asperelloides JM41R (L.1.23), Trichoderma harzianum T-22 (L.1.24);

[0497] 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);

[0498] L3) Microbial pest control agents 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);

[0499] L4) Biochemical pest control agents 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);

[0500] L5) Microbial pest control agents 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).

[0501] Furthermore, the present invention relates to agrochemical compositions comprising 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.

[0502] Furthermore, the present invention relates to agrochemical compositions comprising 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.

[0503] Also preferred are mixtures comprising a biopesticide as pesticidal agent II (component 2), which biopesticide is selected from groups L1), L3) and L5), preferably selected from the strains represented 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.

[0504] Also preferred are mixtures comprising a biopesticide as pesticidal agent II (component 2), said biopesticide being selected from group L1), L3) and L5), preferably from those denoted 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 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 foliar treatment of cultivated plants, preferably vegetables, fruits, vines, cereals, maize and leguminous crops such as soybeans.

[0505] Compositions comprising mixtures of active ingredients can be prepared by customary means, for example by the means given for the compositions of compound I.

[0506] When living microorganisms such as pesticidal agents II from groups L1), L3) and L5) form part of the composition, such compositions can be prepared by customary means (for example H.D. Burges: Formulation of Microbial Biopesticides, Springer, 1998; WO 2008 / 002371, US 6,955,912, US 5,422,107).

[0507] I. Synthesis examples

[0508] Example 1: Preparation of 5-(6-(difluoromethyl)-5-methylpyridin-3-yl)-9-fluoro-1-methyl-1,2-dihydrospiro[benzo[e] [1,4]diazepin -3,1'-cyclopropane]

[0509] Step 1: Preparation of (6-(difluoromethyl)-5-methylpyridin-3-yl)(2,3-difluorophenyl)methanol At 0 °C, under N2, to a solution of 1,2-difluoro-3-iodobenzene (16.8 g, 0.07 mol) in THF (150 mL) was added i-PrMgCl (2 M) (36 mL, 0.073 mol) and the mixture was stirred at 0 °C for 30 min. Then, at 0 °C, 6-(difluoromethyl)-5-methylnicotinaldehyde (10 g, 0.058 mol) in THF was added and the mixture was stirred at 0 °C to 20 °C under N2 for 4 h. TLC (PE:EtOAc = 3:1) showed completion of the reaction. The reaction mixture was quenched with aqueous NH4Cl solution (200 mL), extracted with EtOAc (150 mL) and washed with brine (200 mL). The organic layer was dried over Na2SO4 and concentrated to give (6-(difluoromethyl)-5-methylpyridin-3-yl)(2,3-difluorophenyl)methanol (16.7 g, crude) as a yellow solid. The title compound was used directly without further purification.

[0510] 1 1H NMR (400 MHz, CDCl3) δ [ppm] = 8.38 (s, 1H) 7.54 (s, 1H) 7.20 - 7.25 (m, 1H) 7.02 - 7.09 (m, 2H) 6.45 - 6.75 (m, 1H) 6.14 (s, 1H) 2.40 - 2.44 (m, 3H).

[0511] Step 2: Preparation of (6-(difluoromethyl)-5-methylpyridin-3-yl)(2,3-difluorophenyl)methanone

[0512] To a solution of (6-(difluoromethyl)-5-methylpyridin-3-yl)(2,3-difluorophenyl)methanol (16.7 g, 0.059 mol) in THF (200 mL) was added MnO2 (51 g, 0.59 mol) and the mixture was stirred at 80 °C for 16 h. TLC (PE:EtOAc = 3:1) showed completion of the reaction. The reaction mixture was filtered and the filtrate was concentrated and purified by column (PE:EtOAc = 7:1) to give (6-(difluoromethyl)-5-methylpyridin-3-yl)(2,3-difluorophenyl)methanone (12.5 g, 75%) as a yellow oil. The title compound was used directly without further purification.

[0513] 11H NMR (400 MHz, CDCl3) δ [ppm] = 8.69 (s, 1H) 7.95 (s, 1H) 7.27 - 7.41 (m, 2H) 7.19 - 7.24 (m, 1H) 6.49 - 6.84 (m, 1H) 2.53 (s, 3H).

[0514] Step 3: Preparation of 5-(6-(difluoromethyl)-5-methylpyridin-3-yl)-9-fluoro-1,2-dihydrospiro[benzo[e][1,4]diazepine -3,1'-cyclopropane]

[0515] At 25 °C, Na2CO3 (2.2 g, 20.8 mmol) and 1-(aminomethyl)cyclopropan-1-amine dihydrochloride (1.1 g, 6.9 mmol) were added to a solution of (6-(difluoromethyl)-5-methylpyridin-3-yl)(2,3-difluorophenyl)methanone (1.63 g, 5.8 mmol) in nBuOH (40 mL), and the mixture was stirred under N2 at 120 °C for 16 h. TLC (PE:EtOAc = 1:1) showed completion of the reaction. The mixture was quenched with H2O (50 mL) and extracted with EtOAc (30 mL × 3). The organic layer was washed with brine (20 mL × 2), dried over Na2SO4 and concentrated. The residue was purified by column (PE:EtOAc = 3:1 to 1:1) to give the title compound (1.1 g) as a yellow oil.

[0516] 1 1H NMR (400 MHz, CDCl3) δ [ppm] = 8.47 (s, 1H) 7.72 (s, 1H) 7.05 (ddd, J = 11.19, 7.94, 1.25 Hz, 1H) 6.51 - 6.87 (m, 4H) 4.85 (br s, 1H) 3.60 (d, J = 4.13 Hz, 2H) 2.53 (s, 3H) 1.09 - 1.14 (m, 2H) 0.97 - 1.02 (m, 2H).

[0517] Step 4: Preparation of 5-(6-(difluoromethyl)-5-methylpyridin-3-yl)-9-fluoro-1-methyl-1,2-dihydrospiro[benzo[e][1,4]diazepine -3,1'-cyclopropane]

[0518] At 0 °C, to 5-(6-(difluoromethyl)-5-methylpyridin-3-yl)-9-fluoro-1,2-dihydrospiro[benzo[e][1,4]diazepine A solution of [[2.2 g, 6.6 mmol]] of [[3,1'-bicyclopropyl]] in [[20 mL]] of [[DMF]] was added to [[NaH]] (approx. 60%) [[398 mg, 10 mmol]] and stirred for [[15 min]] at [[0 °C]] under [[N2]]. Then, [[MeI]] [[2.3 g, 16.6 mmol]] was added at [[0 °C]] and the mixture was stirred at [[0 °C]] - [[25 °C]] under [[N2]] for [[16 h]]. [[TLC]] ([[PE:EtOAc]] = [[3:1]]) showed approximately [[65%]] of the desired product and [[30%]] of the starting material in the reaction. The mixture was quenched with an aqueous [[NH4Cl]] solution [[(30 mL)]], and extracted with [[EtOAc]] [[(15 mL × 3)]]. The organic layer was washed with brine [[(15 × 2 mL)]], dried over [[Na2SO4]] and concentrated. The residue was purified by column [[(PE:EtOAc]] = [[3:1]] to [[1:1]]) to give [[5-(6-(difluoromethyl)-5-methylpyridin-3-yl)-9-fluoro-1-methyl-1,2-dihydrospiro[benzo[e][1,4]diazepin]] as a yellow oil. [[3,1'-bicyclopropyl]] [[(1.7 g, 74.6%)]].

[0519] 1 [[1H NMR]] ([[400 MHz]], [[CDCl3]]) δ [[[ppm]]] = [[8.52]] ([[s]], [[1H]]) [[7.91]] ([[br s]], [[1H]]) [[7.12]] ([[br dd]], [[J]] = [[11.38, 7.25 Hz]], [[1H]]) [[6.93]] ([[td]], [[J]] = [[7.88, 4.75 Hz]], [[1H]]) [[6.56 - 6.86]] ([[m]], [[2H]]) [[3.55]] ([[s]], [[2H]]) [[2.99]] ([[d]], [[J]] = [[6.38 Hz]], [[3H]]) [[2.53]] ([[s]], [[3H]]) [[0.77]] ([[br s]], [[4H]]).

[0520] Example 2: [[5-(6-(difluoromethyl)-5-methylpyridin-3-yl)-9-fluoro-1,2,2-trimethyl-2,3-dihydro-1H-benzo[e][1,4]diazepin]]

[0521] Step 1: Preparation of [[tert-butyl (2-((2-(6-(difluoromethyl)-5-methylnicotinoyl)-6-fluorophenyl)amino)-2-methylpropyl)carbamate]]

[0522] To a solution of tert-butyl (2-amino-2-methylpropyl)carbamate (1.66 g, 8.83 mmol) and (6-(difluoromethyl)-5-methylpyridin-3-yl)(2,3-difluorophenyl)methanone (0.5 g, 1.77 mmol) in DMA (15 mL) was added DIEA (0.68 g, 5.30 mmol) and the mixture was stirred under microwave at 200 °C for 4 h. TLC (PE:EtOAc = 5:1) showed the reaction was complete. The reaction mixture was quenched with brine (20 mL). The mixture was extracted with EtOAc (20 mL×3), and the organic layer was washed with brine (50 mL), dried over Na2SO4 and concentrated. The residue was purified by column (PE:EtOAc = 85:15) and concentrated to give the title compound as a yellow oil (0.12 g, yield: 15.0%).

[0523] 1 1H NMR (400 MHz, CDCl3) δ [ppm]=8.65 (s, 1H), 7.90 (s, 1H), 7.18 - 7.27 (m, 3H), 6.62 - 6.90 (m, 2H), 4.97 (br d, J = 3.25 Hz, 1H), 3.32 (br d, J = 5.88 Hz, 2H), 2.60 (s, 3H), 1.44 (s, 9H), 1.26 (s, 6H).

[0524] Step 2: Preparation of 5-(6-(difluoromethyl)-5-methylpyridin-3-yl)-9-fluoro-2,2-dimethyl-2,3-dihydro-1H-benzo[e][1,4]diazepine Preparation

[0525] At 0 °C, to a solution of tert-butyl (2-((2-(6-(difluoromethyl)-5-methylnicotinoyl)-6-fluorophenyl)amino)-2-methylpropyl)carbamate (0.14 g, 0.31 mmol) in DCM (7 mL) was added TFA (1.4 mL), and the mixture was stirred at 0 °C for 4 h. TLC (PE:EtOAc = 1:1) showed the reaction was complete. The reaction mixture was quenched with aqueous NaHCO3 (20 mL), extracted with DCM (10 mL×2), and the organic layer was washed with brine (20 mL), dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (PE:EtOAc = 85:15) and concentrated under reduced pressure to give 5-(6-(difluoromethyl)-5-methylpyridin-3-yl)-9-fluoro-2,2-dimethyl-2,3-dihydro-1H-benzo[e][1,4]diazepine as a yellow oil (50 mg, 49.0%).

[0526] 1 1H NMR (400 MHz, MeOD) δ [ppm] = 8.47 (s, 1H), 7.82 (s, 1H), 7.18 - 7.25 (m, 1H), 6.73 - 7.00 (m, 3H), 3.63 (s, 2H), 2.52 (s, 3H), 1.38 (s, 6H)

[0527] Step 3: 5-(6-(Difluoromethyl)-5-methylpyridin-3-yl)-9-fluoro-1,2,2-trimethyl-2,3-dihydro-1H-benzo[e][1,4]diazepine

[0528] At 0 °C, under N2, to a mixture of 5-(6-(difluoromethyl)-5-methylpyridin-3-yl)-9-fluoro-2,2-dimethyl-2,3-dihydro-1H-benzo[e][1,4]diazepine (70 mg, 0.21 mmol) in DMF (1 mL) was added NaH (60%) (13 mg, 0.31 mmol), and the mixture was stirred at 0 °C for 20 min. Then MeI (45 mg, 0.31 mmol) in DMF (0.5 mL) was added, and the mixture was stirred at 0 °C under N2 for 3 h. LCMS showed completion of the reaction. The reaction mixture was quenched with aqueous NH4Cl solution (10 mL) and extracted with EtOAc (10 × 2 mL). The organic layer was washed with brine (10 mL), dried over Na2SO4 and concentrated. The residue was purified by preparative HPLC (NH4HCO3) to give 5-(6-(difluoromethyl)-5-methylpyridin-3-yl)-9-fluoro-1,2,2-trimethyl-2,3-dihydro-1H-benzo[e][1,4]diazepine (40 mg, 54.9%).

[0529] 1 1H NMR (400 MHz, MeOD) δ [ppm] = 8.54 (d, J = 1.13 Hz, 1H), 7.89 (s, 1H), 7.26 (ddd, J = 12.51, 8.25, 1.38 Hz, 1H), 7.13 (td, J = 7.94, 4.75 Hz, 1H), 6.73 - 7.00 (m, 2H), 3.36 - 3.72 (m, 2H), 2.87 (d, J = 6.00 Hz, 3H), 2.52 (s, 3H), 1.35 (br s, 6H).

[0530] The compounds listed in Table I were prepared in a similar manner.

[0531] Table I: Compounds Ex-1 to Ex-124 having the formula I, wherein R2 , R 3 , R 5 , R 6 , R 7 , R 8 , R 9 The meanings of and Xn are defined in each line.

[0532] *LCMS: Liquid chromatography - mass spectrometry; Shimadzu Nexera LC - 30LCMS - 2020 (ESI+), using HPLC - column Kinetex XB C18 1.7μm (50×2.1mm); 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);

[0533] **LCMS: Liquid chromatography - mass spectrometry; Shimadzu Nexera LC - 30LCMS - 2020 (ESI+), using HPLC - column LUX Cellulose - 1 5μm (150×4.6mm); Eluent: Acetonitrile / water + 0.1% formic acid (gradient from 50:50 to 100:0 in 10 min at 40°C, flow rate 0.6 ml / min);

[0534] R t : Retention time in minutes.

[0535]

[0536]

[0537]

[0538]

[0539]

[0540]

[0541]

[0542]

[0543]

[0544]

[0545]

[0546]

[0547]

[0548]

[0549]

[0550] #imgpt158#

[0551] II. Biological examples

[0552] Greenhouse

[0553] The compound is 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 give a total volume of 5 ml. Subsequently, water is added to a total volume of 100 ml.

[0554] This stock solution is then diluted with the solvent-emulsifier-water mixture to the final concentrations given in the table below.

[0555] Example 1 - Preventive fungicidal control of Botrytis cinerea on green pepper leaves

[0556] Green pepper seedlings are grown in pots to the 4 - 5 leaf stage. These plants are sprayed to runoff with the aforementioned spray solution containing the active ingredient or mixture at the concentrations mentioned in the table below. The next day, the plants are inoculated with a biological malt aqueous solution or DOB solution containing a suspension of Botrytis cinerea spores. The plants are then immediately transferred to a humidity 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 % diseased leaf area.

[0557] In this test, samples treated with 250 ppm of the active substances from Examples Ex-5, Ex-6, Ex-7, Ex-8, Ex-29, Ex-30, Ex-32, and Ex-33 showed a pathogen growth rate of up to at most 13%, while 90% of the untreated plants were infected.

[0558] In this test, samples treated with 125 ppm of the active substances from Examples Ex-43, Ex-45, Ex-47, Ex-48, Ex-52, Ex-53, Ex-54, Ex-55, Ex-57, Ex-58, Ex-59, Ex-60, Ex-61, Ex-62, Ex-63, Ex-64, Ex-65, Ex-66, Ex-67, Ex-68, Ex-69, Ex-70, Ex-71, Ex-75, Ex-76, Ex-77, Ex-78, Ex-85, Ex-88, Ex-89, Ex-90, Ex-91, Ex-92, Ex-93, Ex-95, Ex-96, Ex-97, Ex-102, Ex-110 showed a pathogen growth rate of up to a maximum of 22%, while 90% of the untreated plants were infected.

[0559] Example 2 - Long-term control of Botrytis cinerea on green pepper leaves

[0560] Green pepper seedlings were grown in pots to the 4- to 5-leaf stage. These plants were sprayed to runoff with the aforementioned spray solution containing the active ingredient or mixture at the concentrations mentioned in the following table. Then, the plants were cultivated in a greenhouse for 7 days and then inoculated with a biological malt aqueous solution or DOB solution containing a Botrytis cinerea spore suspension. The plants were then immediately transferred to a humidity chamber. After 5 days at 22°C to 24°C and saturated relative humidity, the degree of fungal infestation on the leaves was visually evaluated as % diseased leaf area.

[0561] In this test, samples treated with 63 ppm of the active substances from Examples Ex-5, Ex-6, Ex-7, and Ex-8 showed a pathogen growth rate of up to a maximum of 17%, while 90% of the untreated plants were infected.

[0562] Example 3 - Preventive fungicidal control of white mold on soybeans caused by Sclerotinia sclerotiorum

[0563] Soybean seedlings were planted in pots. These plants were sprayed to runoff with the aforementioned spray solution containing the active ingredient or mixture at the concentrations mentioned in the following table. The next day, the treated plants were inoculated with a biological malt suspension containing Sclerotinia sclerotiorum mycelium. Then, the test plants were cultivated in a greenhouse at 23°C and a relative humidity between 80% and 85% for 6 days. The degree of fungal infestation on the leaves was visually evaluated as % diseased leaf area.

[0564] In this test, samples treated with 250 ppm of the active substances from Examples Ex-29, Ex-30, Ex-32, and Ex-33 showed a pathogen growth rate of up to a maximum of 14%, while 100% of the untreated plants were infected.

[0565] Example 4 - Preventive fungicidal control of Sclerotinia rot on oilseed rape

[0566] The oilseed rape was grown in pots 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 mixture at the concentrations mentioned in the following table. 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 sclerotiorum 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.

[0567] In this test, the samples treated with the active substances at 100 g / ha from Examples Ex - 18, Ex - 29, Ex - 32 and Ex - 33 respectively showed a pathogen growth rate of up to at most 2%, while the untreated plants were 100% infected.

[0568] Example 5 - Preventive fungicidal control of Sclerotinia rot on cabbage

[0569] The cabbage was grown in pots 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 mixture at the concentrations mentioned in the following table. The plants could be air - dried. The next day, the cabbage leaves were inoculated with 50 μl of a mixture of ground petals, methyl cellulose, water and yeast - bacteria - peptone medium (containing spores of Sclerotinia sclerotiorum). After 8 days at 21 °C and 60% relative humidity, the degree of fungal infestation on the leaves was visually evaluated as % diseased leaf area.

[0570] In this test, the samples treated with the active substances at 125 ppm from Examples Ex - 45, Ex - 52, Ex - 53, Ex - 55, Ex - 57, Ex - 58, Ex - 59, Ex - 60, Ex - 61, Ex - 71, Ex - 75, Ex - 78, Ex - 91, Ex - 93, Ex - 95 respectively showed a pathogen growth rate of up to at most 20%, while the untreated plants were 80% infected.

[0571] Microtest

[0572] The active compound was formulated separately as a stock solution at a concentration of 10000 ppm in dimethyl sulfoxide.

[0573] Example 6 - Activity against Botrytis cinerea in microtiter plate tests

[0574] Mix the stock solutions in proportion, pipette them onto a microtiter plate (MTP), and dilute with water to the specified concentration. Then add a spore suspension of Botrytis cinerea in an aqueous solution of biological malt or a yeast-bacterial peptone-sodium acetate solution. Place these plates in a water vapor-saturated chamber at a temperature of 18 °C. Measure the MTP at 405 nm 7 days after inoculation using an absorption photometer.

[0575] In this test, samples treated with the active substances at 31 ppm from Examples Ex-1, Ex-3, Ex-4, Ex-5, Ex-5, Ex-6, Ex-7, Ex-8, Ex-11, Ex-12, Ex-15, Ex-16, Ex-18, Ex-19, Ex-20, Ex-22, Ex-23, Ex-24, Ex-28, Ex-29, Ex-30, Ex-31, Ex-32, Ex-33, Ex-34, Ex-35, Ex-36, Ex-37, Ex-38, Ex-48, Ex-52, Ex-53, Ex-54, Ex-55, Ex-56, Ex-57, Ex-58, Ex-59, Ex-60, Ex-61, Ex-62, Ex-63, Ex-64, Ex-65, Ex-66, Ex-67, Ex-68, Ex-69, Ex-70, Ex-71, Ex-72, Ex-73, Ex-74, Ex-75, Ex-76, Ex-77, Ex-78, Ex-79, Ex-80, Ex-81, Ex-82, Ex-85, Ex-86, Ex-87, Ex-88, Ex-89, Ex-90, Ex-91, Ex-92, Ex-93, Ex-94, Ex-95, Ex-96, Ex-97, Ex-98, Ex-99, Ex-100, Ex-101, Ex-102, Ex-103, Ex-104, Ex-105, Ex-106, Ex-107, Ex-108, Ex-109, Ex-110, Ex-111, Ex-113, Ex-115, Ex-116, Ex-117, Ex-118 showed a 14% pathogen growth rate.

[0576] Example 7 - Activity against Cercospora sojina in the microtiter plate test

[0577] Prepare a stock solution of the active compound alone at a concentration of 10,000 ppm in dimethyl sulfoxide. Mix the stock solutions in proportion, pipette them onto a microtiter plate (MTP), and dilute with water to the specified concentration. Then add a spore suspension of Cercospora sojina in an aqueous solution of biological malt or a yeast-bacterial peptone-sodium acetate solution.

[0578] In this test, samples treated with 31 ppm of the active substances from Examples Ex-29, Ex-32, Ex-33, Ex-47, Ex-48, Ex-57, E-59, Ex-60, Ex-61, Ex-72, Ex-75, Ex-76, Ex-78, Ex-88, Ex-89, Ex-90, Ex-91, Ex-92, Ex-95, Ex-97 showed a 20% pathogen growth rate.

[0579] Example 8 - Activity of the CORYCA-G G413A mutant against Corynespora cassiicola in a microtiter plate test

[0580] 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 the Corynespora cassiicola G413A mutant isolate in a biological malt aqueous solution or a yeast-bacterial peptone-sodium acetate solution was added.

[0581] In this test, samples treated with 31 ppm of the active substances from Examples Ex-29, Ex-32, Ex-33, Ex-43, Ex-45, Ex-47, Ex-48, Ex-52, Ex-53, Ex-54, Ex-55, Ex-56, Ex-57, Ex-58, Ex-59, Ex-60, Ex-61, Ex-62, Ex-63, Ex-64, Ex-65, Ex-66, Ex-67, Ex-68, Ex-69, Ex-70, Ex-71, Ex-72, Ex-85, Ex-86, Ex-89, Ex-90 showed a 21% pathogen growth rate.

[0582] Example 9 - Activity against Fusarium culmorum in a microtiter plate test

[0583] 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 a yeast-bacterial peptone-glycerol or DOB solution was added.

[0584] In this test, samples treated with 31 ppm of the active substances from Examples Ex-2, Ex-3, Ex-5, Ex-5, Ex-6, Ex-8, Ex-26, Ex-28, Ex-29, Ex-30, Ex-32, Ex-33, Ex-35, Ex-36, Ex-37, Ex-38, Ex-48, Ex-52, Ex-54, Ex-57, Ex-63, Ex-64, Ex-65, Ex-66, Ex-67, Ex-69, Ex-70, Ex-71, Ex-72, Ex-75, Ex-76, Ex-77, Ex-78, Ex-85, Ex-86, Ex-87, Ex-95, Ex-98, Ex-99, Ex-103, Ex-110, Ex-113, Ex-117, Ex-118 showed a 21% pathogen growth rate.

[0585] Example 10 - Activity against leaf spot on wheat caused by Septoria tritici in a microtiter plate test

[0586] 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 Septoria tritici in a biological malt aqueous solution or yeast - bacterial peptone - glycerol or DOB solution was added.

[0587] In this test, samples treated with 31 ppm of the active substances from Examples Ex-6, Ex-8, Ex-29, Ex-32, Ex-52, Ex-62, Ex-69, Ex-70, Ex-72, Ex-75, Ex-76, Ex-77, Ex-78, Ex-81, Ex-85, Ex-88, Ex-89, Ex-90, Ex-93 showed a 22% pathogen growth rate.

[0588] Example 11 - Activity against leaf spot on wheat caused by Alternaria solani in a microtiter plate test

[0589] 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 Alternaria solani in a biological malt aqueous solution or yeast - bacterial peptone - glycerol or DOB solution was added.

[0590] In this test, samples treated with 31 ppm of the active substances from Examples Ex-43, Ex-45, Ex-47, Ex-48, Ex-52, Ex-53, Ex-54, Ex-55, Ex-57, Ex-58, Ex-60, Ex-62, Ex-64, Ex-66, Ex-67, Ex-69, Ex-70, Ex-71, Ex-72, Ex-76, Ex-85, Ex-86 showed a pathogen growth rate of up to 21%.

[0591] Example 12 - Activity against leaf spot on wheat caused by Cercospora beticola in a microtiter plate test

[0592] The active compound was formulated individually 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 Cercospora beticola in a biological malt aqueous solution or yeast - bacteriological peptone - glycerol or DOB solution was added.

[0593] In this test, samples treated with 31 ppm of the active substances from Examples Ex-48, Ex-53, Ex-72, Ex-75, Ex-76, Ex-85, Ex-88, Ex-89, Ex-90, Ex-92, Ex-95 showed a pathogen growth rate of up to 18%.

[0594] Example 13 - Activity against leaf spot on wheat caused by Cercospora zeae - maydis in a microtiter plate test

[0595] The active compound was formulated individually 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 Cercospora zeae - maydis in a biological malt aqueous solution or yeast - bacteriological peptone - glycerol or DOB solution was added.

[0596] In this test, samples treated with 31 ppm of the active substances from Examples Ex-48, Ex-57, Ex-69, Ex-75, Ex-76, Ex-78, Ex-85, Ex-86, Ex-89, Ex-91, Ex-92, Ex-95 showed a pathogen growth rate of up to 17%.

[0597] Example 14 - Activity against leaf spot on wheat caused by Pyricularia oryzae in a microtiter plate test

[0598] The active compound was separately formulated into 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 Pyricularia oryzae in a biological malt aqueous solution or yeast - bacterial peptone - glycerol or DOB solution was added.

[0599] In this test, samples treated with 31 ppm of the active substances from Examples Ex - 43, Ex - 45, Ex - 47, Ex - 52, Ex - 53, Ex - 54, Ex - 55, Ex - 56, Ex - 57, Ex - 58, Ex - 59, Ex - 60, Ex - 61, Ex - 62, Ex - 63, Ex - 64, Ex - 66, Ex - 67, Ex - 68, Ex - 69, Ex - 70, Ex - 71, Ex - 76, Ex - 89 showed a pathogen growth rate of up to 22%.

[0600] The measured parameters were compared with the growth rate (100%) of the control variant without the active compound and the fungus - free blank value to determine the relative growth rate (in %) of the pathogen in the respective active compound.

Claims

1. A compound of formula I or its N-oxide, tautomer, stereoisomer or agriculturally acceptable salt Y is N, CR 1 ; 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; 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 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 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 atoms 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 heterocycle containing 1, 2 or 3 heteroatoms selected from O and S as ring members; R 9 independently selected in each case from 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.

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 (=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. The compound according to any one of claims 1 to 11, wherein, X is selected from halogen, C1-C6-alkyl, O-C1-C6-alkyl, O-C1-C6-haloalkyl.

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

14. 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 12, or with a composition as defined in any one of claims 13.

15. A seed coated with 0.1 to 10 kg / 100 kg of seed amount of at least one compound of formula I as defined in any one of claims 1 to 12 or its agriculturally acceptable salt, or a composition as defined in any one of claims 13.

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