Substituted benzodiazepines as fungicides

Abstract

The present 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 benzodiazepine compounds as fungicides 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 benzodiazepine 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 benzodiazepine compounds of formula (I) as defined below and their agriculturally suitable embodiments.

[0004] Accordingly, the present invention relates to compounds of formula I as fungicides

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

[0009] R 5 is hydrogen, halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl or benzyl, a heterocyclic aromatic group and a CH2-heterocyclic aromatic group, where the last-mentioned 10 aliphatic or aromatic groups are unsubstituted or carry 1, 2 or 3 substituents R 5a ; where

[0010] each R 5a is independently halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl or O-C1-C6-alkyl;

[0011] R 6is hydrogen, halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl or benzyl, a heteroaromatic group and a CH2-heteroaromatic group, where the last-mentioned 10 aliphatic or aromatic groups are unsubstituted or carry 1, 2 or 3 substituents R 6a ; where

[0012] each R 6a independently is halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl or O-C1-C6-alkyl;

[0013] or

[0014] R 5 and R 6 together form an oxo group (=O); or a thio group (=S);

[0015] or

[0016] R 5 and R 6 together with the carbon atom to which they are bonded form a 3-, 4-, 5- or 6-membered saturated carbocyclic 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; where the carbocyclic or heterocyclic ring is unsubstituted or carries 1, 2 or 3 substituents R 56 ; where

[0017] each R 56 independently is halogen, C1-C6-alkyl or C1-C6-haloalkyl;

[0018] R 7 is hydrogen, halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl or benzyl, a heteroaromatic group and a CH2-heteroaromatic group, where the last-mentioned 10 aliphatic or aromatic groups are unsubstituted or carry 1, 2 or 3 substituents R 7a ; where

[0019] each R 7a independently is halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl or O-C1-C6-alkyl;;

[0020] R 8is hydrogen, halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl or benzyl, a heteroaromatic group and a CH2-heteroaromatic group, where the last-mentioned 10 aliphatic or aromatic groups are unsubstituted or carry 1, 2 or 3 substituents R 8a ; where

[0021] each R 8a is independently halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl or O-C1-C6-alkyl;

[0022] or

[0023] R 7 and R 8 together with the carbon atom to which they are bonded form a 3-, 4-, 5- or 6-membered saturated carbon ring or a 3-, 4-, 5- or 6-membered saturated heterocyclic ring containing 1, 2 or 3 heteroatoms selected from O and S as ring members;

[0024] R 9 is 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; where the heteroaryl contains 1, 2 or 3 heteroatoms selected from N, O and S as ring members; where the benzene ring in the aryl and benzyl is unsubstituted or carries 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; where the benzene ring in the benzyl is unsubstituted or carries 1, 2 or 3 substituents selected from the group consisting of: CN and halogen;

[0025] where

[0026] 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 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;

[0027] X is independently 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;

[0028] n is 0, 1, 2 or 3;

[0029] Z is independently 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;

[0030] m is 0, 1, 2 or 3;

[0031] or an N-oxide, tautomer, stereoisomer or agriculturally acceptable salt thereof, provided that

[0032] if Y is CR 1 , then R 5 , R 6 , R 7 , R 8 cannot all be H;

[0033] if Y is CR 1 , and R 5 , R 6 is CH3, and R 7 , R 8 is H, then R 9 cannot be CH3; and

[0034] if Y is CR 1 , and if R 5 , R 6 is H, and R 7 , R 8 is CH3, then R 9 cannot be CH3, allyl, benzyl.

[0035] 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.

[0036] The agriculturally acceptable salts of the compounds of formula I especially 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. Thus, suitable cations are especially 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 ammonium ions, 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.

[0037] The anions of the acceptable acid addition salts are mainly chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of C1 - C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting compound I with an acid of the corresponding anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.

[0038] The compounds of formula I can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereoisomers, atropisomers resulting from restricted rotation about a single bond around 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), individual stereoisomers, or as optically active forms.

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

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

[0041] Hereinafter, intermediate compounds are further described. The person skilled in the art will readily understand that the preferred options for 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.

[0042] If the synthesis gives rise to 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 can also occur after use, for example in the treated plant in the case of plant treatment or in the harmful fungi to be controlled.

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

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

[0045] The term "C1-C6-alkyl" refers to a straight-chain or branched-chain saturated hydrocarbon group having 1 to 6 carbon atoms, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, and 1-ethyl-2-methylpropyl. Similarly, the term "C2-C4-alkyl" refers to a straight-chain or branched-chain alkyl group having 2 to 4 carbon atoms, such as ethyl, propyl (n-propyl), 1-methylethyl (isopropyl), butyl, 1-methylpropyl (sec-butyl), 2-methylpropyl (isobutyl), 1,1-dimethylethyl (tert-butyl).

[0046] The term "C1-C6-haloalkyl" refers to an alkyl group having 1 or 6 carbon atoms as defined above, wherein some or all of the hydrogen atoms in these groups can be replaced by halogen atoms as described above. Examples are "C1-C2-haloalkyl" groups such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, or pentafluoroethyl.

[0047] The term "C2-C6-alkenyl" refers to a straight-chain or branched-chain unsaturated hydrocarbon group having 2 to 6 carbon atoms and having a double bond at any position. Examples are "C2-C4-alkenyl" groups such as vinyl, 1-propenyl, 2-propenyl (allyl), 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl.

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

[0049] The term "C2-C6-alkynyl" refers to a straight-chain or branched-chain unsaturated hydrocarbon group having 2 to 6 carbon atoms and containing at least one triple bond. Examples are "C2-C4-alkynyl" groups such as ethynyl, prop-1-ynyl, prop-2-ynyl (propargyl), but-1-ynyl, but-2-ynyl, but-3-ynyl, 1-methyl-prop-2-ynyl.

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

[0051] The term "C3-C6-cycloalkyl" refers to a monocyclic saturated hydrocarbon group having 3 to 6 carbon ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl. Thus, saturated three-, four-, five-, six-, seven-, eight-, nine- or ten-membered carbocyclic groups or carbocycles are "C3-C 10 -cycloalkyl".

[0052] The term "C3-C8-cycloalkyl-C1-C4-alkyl" refers to an alkyl group having 1 to 4 carbon atoms (as defined above), 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).

[0053] The term "saturated or partially unsaturated three-, four-, five-, six-, seven-, eight-, nine- or ten-membered heterocyclic group or heterocycle, wherein the heterocyclic group or heterocycle contains 1, 2, 3 or 4 heteroatoms selected from N, O and S" should 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:

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

[0055] A 5- or 6-membered saturated or partially unsaturated heterocycle containing 1, 2 or 3 heteroatoms selected from the group consisting of O, N and S as ring members, such as 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl, 1,3,4-triazol-2-yl, 2,3-dihydrofuran-2-yl, 2,3-dihydrofuran-3-yl, 2,4-dihydrofuran-2-yl, 2,4-dihydrofuran-3-yl, 2,3-dihydrothiophen-2-yl, 2,3-dihydrothiophen-3-yl, 2,4-dihydrothiophen-2-yl, 2,4-dihydrothiophen-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-dihydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 2-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,

[0056] 7-membered saturated or partially unsaturated heterocycles such as tetra- and hexahydroazepinyl, such as 2,3,4,5-tetrahydro[1H]azepin- -1-, -2-, -3-, -4-, -5-, -6- or -7-yl, 3,4,5,6-tetrahydro[2H]azepin- -2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,4,7-tetrahydro[1H]azepin- -1-, -2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,6,7-tetrahydro[1H]azepin- -1-, -2-, -3-, -4-, -5-, -6- or -7-yl, hexahydroazepin- -1-, -2-, -3- or -4-yl, tetra- and hexahydrooxepinyl, such as 2,3,4,5-tetrahydro[1H]oxepin- -2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,4,7-tetrahydro[1H]oxepin- -2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,6,7-tetrahydro[1H]oxepin- -2-, -3-, -4-, -5-, -6- or -7-yl, hexahydrooxepin- -1-, -2-, -3- or -4-yl, tetra- and hexahydro-1,3-diazepinyl, tetra- and hexahydro-1,4-diazepinyl, tetra- and hexahydro-1,3-oxazepinyl, tetra- and hexahydro-1,4-oxazepinyl, tetra- and hexahydro-1,3-dioxepinyl, tetra- and hexahydro-1,4-dioxepinyl, and the corresponding -ylidene groups.

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

[0058] The term "5- or 6-membered heteroaryl" or "5- or 6-membered heteroaromatic group" refers to an aromatic ring system 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

[0059] 5-membered heteroaryl, such as pyrrol-1-yl, pyrrol-2-yl, pyrrol-3-yl, thiophen-2-yl, thiophen-3-yl, furan-2-yl, furan-3-yl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1,2,4-triazol-1-yl, 1,2,4-triazol-3-yl, 1,2,4-triazol-5-yl, 1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, and 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl; or

[0060] 6-membered heteroaryl, such as pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazin-2-yl, and 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl.

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

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

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

[0064] According to one embodiment of the compound having Formula I, R 4independently selected from H, halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl in each case, preferably R 4 independently selected from H, C1-C4-alkyl, C1-C4-haloalkyl in each case, more preferably R 4 independently selected from H, C1-C4-alkyl in each case, most preferably R 4 is H in each case.

[0065] According to one embodiment of the compound of 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, 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 5a ; where each R 5a is independently halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl or O-C1-C6-alkyl.

[0066] According to one embodiment of the compound of formula I, R 5 is independently selected 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) in each case, where phenyl and CH2-phenyl are unsubstituted or substituted by one or two halogens.

[0067] According to a further embodiment of the compound of formula I, R 5 is CH3 or CF3.

[0068] According to a further embodiment of the compound of formula I, R 5 is CH3.

[0069] 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.

[0070] According to a further embodiment of the compound of formula I, R 5 is CH=CH2, CH2CH=CH2.

[0071] 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.

[0072] According to an embodiment of the compound of formula I, R 6 is in each case 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; 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.

[0073] According to an embodiment of the compound of formula I, R 6 is in each case independently selected from C1-C6-alkyl (Example 6.1), C1-C6-alkyl-O-phenyl (Example 6.2), C1-C6-alkyl-O-C1-C6-alkyl (Example 6.3).

[0074] 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.

[0075] 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.

[0076] According to a further embodiment of the compound of formula I, R 5 and R6 Form a C3-C6-cycloalkyl (Example 6.4).

[0077] 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 selected from the group consisting of O and S.

[0078] According to a further embodiment of the compound of formula I, R 5 and R 6 together form a (=O) group (Example 6.5).

[0079] Preferred embodiments of R 5 , R 6 of the present invention are in Table P5 below, where each row from P5-1 to P5-19 corresponds to a specific embodiment of the present invention, and where P5-1 to P5-19 can also be arbitrarily combined with each other to be preferred embodiments of the present invention. The point of attachment of the carbon atom bonded to R 5 and R 6 is marked with "#" in the figure.

[0080] Table P5,6:

[0081]

[0082]

[0083] According to an embodiment of the compound of formula I, R 7 is in each case 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; 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.

[0084] According to an embodiment of the compound of formula I, R 7independently selected in each case from C1-C6-alkyl (Example 7.1), C1-C6-haloalkyl (Example 7.2), C1-C6-alkyl-O-C1-C6-alkyl (Example 7.3), phenyl, CH2-phenyl (Example 7.4), where phenyl and CH2-phenyl are unsubstituted or substituted by one or two halogens.

[0085] According to a further embodiment of the compound of formula I, R 7 is CH3 or CF3.

[0086] According to a further embodiment of the compound of formula I, R 7 is CH3.

[0087] 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.

[0088] 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.

[0089] According to an embodiment of the compound of formula I, R 8 is independently selected in each case from hydrogen, halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, benzyl, five- or six-membered heteroaryl or five- or six-membered CH2-heteroaryl; where the heteroaryl contains one, two or three heteroatoms selected from N, O and S; and where these aliphatic or aromatic groups are unsubstituted or carry 1, 2 or 3 substituents R 8a ; where each R 8a is independently halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl or O-C1-C6-alkyl.

[0090] According to an embodiment of the compound of formula I, R 8 is independently selected in each case from C1-C6-alkyl (Example 8.1), C1-C6-alkyl-O-phenyl (Example 8.2), C1-C6-alkyl-O-C1-C6-alkyl (Example 8.3).

[0091] 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.

[0092] 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.

[0093] According to a further embodiment of the compound of formula I, R 7 and R 8 form a C3-C6-cycloalkyl (Example 8.4).

[0094] 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.

[0095] Preferred embodiments of R 7 , R 8 of the present invention are in Table P78 below, where each row from P7-1 to P7-18 corresponds to a specific embodiment of the present invention, and where P7-1 to P7-18 can also be arbitrarily combined with each other as preferred embodiments of the present invention. The point of attachment of the carbon atom bonded to R 7 and R 8 is marked with "#" in the figure.

[0096] Table P7,8:

[0097]

[0098] According to a further embodiment of the compound of formula I,

[0099] R 9independently 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 in each case 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;

[0100] wherein

[0101] 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.

[0102] In yet another embodiment according to formula I, R 9 is Cl, F.

[0103] In yet another embodiment according to formula I, R 9 is CN, CH2CN or CH(CH3)CN.

[0104] In another specific embodiment according to formula I, R 9 is CH(=O).

[0105] In another specific embodiment according to formula I, R 9 is OCH3 or OCH2CH3.

[0106] In another specific embodiment according to formula I, R 9is C(=O)C1-C6-alkyl, wherein the alkyl is CH3, C2H5, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl or isopentyl.

[0107] In another specific embodiment according to Formula I, R 9 is C(=O)C2-C6-alkenyl, wherein the alkenyl is CH=CH2, CH2CH=CH2.

[0108] In another specific embodiment according to Formula I, R 9 is C(=O)C2-C6-alkynyl, wherein the alkynyl is CΞCH, CH2CΞCH.

[0109] In another specific embodiment according to Formula I, R 9 is C(=O)C3-C6-cycloalkyl, wherein the cycloalkyl is cyclopropyl (C3H7) or cyclobutyl (C4H9).

[0110] 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, wherein the alkyl is CH3, C2H5, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl.

[0111] In yet another embodiment according to Formula I, R 9 is C1-C6-alkyl, such as CH3, C2H5, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl or isopentyl.

[0112] In yet another embodiment according to Formula I, R 9 is C1-C6-alkyl, especially C1-C4-alkyl, such as CH3, C2H5, n-propyl, isopropyl.

[0113] In yet another embodiment according to Formula I, R 9 is C1-C6-haloalkyl, especially C1-C4-haloalkyl, such as CF3, CCl3, FCH2, ClCH2, F2CH, Cl2CH, CF3CH2, CCl3CH2 or CF2CHF2.

[0114] In yet another embodiment according to Formula I, R 9 is C3-C6-cycloalkyl, especially cyclopropyl.

[0115] In yet another embodiment according to Formula I, R 9 is C3-C6-halocycloalkyl. In a specific embodiment, R 9b is a fully or partially halogenated cyclopropyl, such as 1-F-cyclopropyl, 1-Cl-cyclopropyl, 1,1-F2-cyclopropyl, 1,1-Cl2-cyclopropyl.

[0116] In yet another embodiment according to formula I, R 9 is C2-C6-alkenyl, especially C2-C4-alkenyl, such as CH=CH2, C(CH3)=CH2, CH2CH=CH2.

[0117] In another specific embodiment according to formula I, R 9 is C2-C6-haloalkenyl, especially C2-C4-haloalkenyl, more specifically 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.

[0118] In yet another embodiment according to formula I, R 9 is C2-C6-alkynyl or C2-C6-haloalkynyl, especially C2-C4-alkynyl or C2-C4-haloalkynyl, such as C≡CH, CH2C≡CH.

[0119] In yet another embodiment according to formula I, R 9 is -S(=O)2-R 9a wherein R 9a is preferably C1-C6-alkyl, especially C1-C4-alkyl, such as CH3, C2H5, n-propyl, isopropyl.

[0120] In yet another embodiment according to formula I, R 9 is aryl, especially phenyl, wherein the aryl or phenyl moiety is in each case unsubstituted or substituted by the same or different groups R 9b independently of one another selected from the following: 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 unsubstituted phenyl. According to another embodiment, R 9 is phenyl substituted by one, two or three (especially one) halogen atoms especially selected from F, Cl and Br, more specifically selected from F and Cl.

[0121] In yet another embodiment according to formula I, R 9is 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.

[0122] According to yet another embodiment of 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.

[0123] According to yet another embodiment of formula I, R 9 is independently selected in each case from H, halogen, OH, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy and C3-C6-cycloalkyl, where the acyclic moiety of R 9 is unsubstituted or substituted by the same or different groups R as defined and preferably as defined herein 9a and where the carbocyclic, phenyl and heteroaryl moieties of R 9 are unsubstituted or substituted by the same or different groups R as defined and preferably as defined herein 9b substituted.

[0124] Particularly preferred embodiments of R according to the invention 9 are in Table P9 below, where each row of rows P9-1 to P9-31 corresponds to a specific embodiment of the invention, and where P9-1 to P9-31 are also preferably combined with each other in any combination. The point of attachment of the carbon atom bonded to R 9 is marked with "#" in the figure.

[0125] Table P9:

[0126]

[0127] 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).

[0128] According to one embodiment of the compound of formula I, X is independently selected in each case from halogen, O-C1-C6-alkyl.

[0129] According to one embodiment of the compound of formula I, X is independently selected in each case from F or Cl.

[0130] According to one embodiment of the compound of formula I, X is C3-C6-cycloalkyl.

[0131] According to one embodiment of the compound of formula I, n is 0.

[0132] According to one embodiment of the compound of formula I, n is 1.

[0133] According to one embodiment of the compound of formula I, n is 2.

[0134] According to one embodiment, Xn is defined as follows:

[0135]

[0136] and X is selected from F, Cl, I, CH3, cyclopropyl, CH=CH2, CΞCH, OCH3, OCHF2, CF3, CHF2, CH2CH3, CN.

[0137] According to one embodiment, Xn is defined as follows:

[0138]

[0139] and X is F.

[0140] According to one embodiment, Xn is defined as follows:

[0141]

[0142] and X is selected from F, Cl, I, CH3, cyclopropyl, CH=CH2, CΞCH, OCH3, OCHF2, CF3, CHF2, CH2CH3, CN.

[0143] According to one embodiment, Xn is defined as follows:

[0144]

[0145] and X is F.

[0146] According to one embodiment, n is 0.

[0147] According to one embodiment of the compound of formula I, Z is H.

[0148] According to one embodiment of the compound of formula I (Embodiment Z.1), Z is independently selected in each case from halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, O-C1-C6-alkyl.

[0149] According to one embodiment of the compound of formula I (Embodiment Z.2), Z is independently selected in each case from halogen.

[0150] According to one embodiment of the compound of formula I (Embodiment Z.3), Z is independently selected in each case from F and Cl.

[0151] According to one embodiment of the compound of formula I (Embodiment Z.4), Z is defined in sub-formulas (z.1 to z.23).

[0152]

[0153] According to one embodiment of the compound of formula I, m is 0.

[0154] According to one embodiment of the compound of formula I, m is 1.

[0155] In a further aspect, the present invention relates to Embodiments E.1 to E.300 listed in Table E, which represent preferred combinations of the embodiments defined above for each of the variables R 2 , R 3 and X (represented by Embodiments X.1 to X.6), and n in the compound of formula I is defined as follows.

[0156]

[0157] Table E:

[0158]

[0159]

[0160]

[0161]

[0162]

[0163]

[0164]

[0165]

[0166]

[0167]

[0168] In another aspect, the present invention relates to Examples E.1 to E.300 listed in Table E, wherein R 5 is represented by Example 5.1, and R 6 is represented by Example 6.1.

[0169] In another aspect, the present invention relates to Examples E.1 to E.300 listed in Table E, wherein R 5 is represented by Example 5.2, and R 6 is represented by Example 6.1.

[0170] In another aspect, the present invention relates to Examples E.1 to E.300 listed in Table E, wherein R 5 is represented by Example 5.3, and R 6 is represented by Example 6.1.

[0171] In another aspect, the present invention relates to Examples E.1 to E.300 listed in Table E, wherein R 5 is represented by Example 5.4, and R 6 is represented by Example 6.1.

[0172] In another aspect, the present invention relates to Examples E.1 to E.300 listed in Table E, wherein R 5 is represented by Example 5.1, and R 6 is represented by Example 6.2.

[0173] In another aspect, the present invention relates to Examples E.1 to E.300 listed in Table E, wherein R 5 is represented by Example 5.2, and R 6 is represented by Example 6.2.

[0174] In another aspect, the present invention relates to Examples E.1 to E.300 listed in Table E, wherein R 5 is represented by Example 5.3, and R 6 is represented by Example 6.2.

[0175] In another aspect, the present invention relates to Examples E.1 to E.300 listed in Table E, wherein R 5represented by Example 5.4, and R 6 represented by Example 6.2.

[0176] In a further aspect, the present invention relates to Examples E.1 to E.300 listed in Table E, where R 5 is represented by Example 5.1, and R 6 is represented by Example 6.3.

[0177] In a further aspect, the present invention relates to Examples E.1 to E.300 listed in Table E, where R 5 is represented by Example 5.2, and R 6 is represented by Example 6.3.

[0178] In a further aspect, the present invention relates to Examples E.1 to E.300 listed in Table E, where R 5 is represented by Example 5.3, and R 6 is represented by Example 6.3.

[0179] In a further aspect, the present invention relates to Examples E.1 to E.300 listed in Table E, where R 5 is represented by Example 5.4, and R 6 is represented by Example 6.3.

[0180] In a further aspect, the present invention relates to Examples E.1 to E.300 listed in Table E, where R 5 and R 6 are represented by Example 6.4.

[0181] In a further aspect, the present invention relates to Examples E.1 to E.300 listed in Table E, where R 5 and R 6 are represented by Example 6.5.

[0182] In a further aspect, the present invention relates to Examples E.1 to E.300 listed in Table E, where R 7 is represented by Example 7.1, and R 8 is represented by Example 8.1.

[0183] In a further aspect, the present invention relates to Examples E.1 to E.300 listed in Table E, where R 7 is represented by Example 7.2, and R 8 is represented by Example 8.1.

[0184] In a further aspect, the present invention relates to Examples E.1 to E.300 listed in Table E, where R 7 is represented by Example 7.3, and R 8 is represented by Example 8.1.

[0185] In another aspect, the present invention relates to Examples E.1 to E.300 listed in Table E, where R 7 is represented by Example 7.4, and R 8 is represented by Example 8.1.

[0186] In another aspect, the present invention relates to Examples E.1 to E.300 listed in Table E, where R 7 is represented by Example 7.1, and R 8 is represented by Example 8.2.

[0187] In another aspect, the present invention relates to Examples E.1 to E.300 listed in Table E, where R 7 is represented by Example 7.2, and R 8 is represented by Example 8.2.

[0188] In another aspect, the present invention relates to Examples E.1 to E.300 listed in Table E, where R 7 is represented by Example 7.3, and R 8 is represented by Example 8.2.

[0189] In another aspect, the present invention relates to Examples E.1 to E.300 listed in Table E, where R 7 is represented by Example 7.4, and R 8 is represented by Example 8.2.

[0190] In another aspect, the present invention relates to Examples E.1 to E.300 listed in Table E, where R 7 is represented by Example 7.1, and R 8 is represented by Example 8.3.

[0191] In another aspect, the present invention relates to Examples E.1 to E.300 listed in Table E, where R 7 is represented by Example 7.2, and R 8 is represented by Example 8.3.

[0192] In another aspect, the present invention relates to Examples E.1 to E.300 listed in Table E, where R 7 is represented by Example 7.3, and R 8 is represented by Example 8.3.

[0193] In another aspect, the present invention relates to Examples E.1 to E.300 listed in Table E, where R 7 is represented by Example 7.4, and R 8 is represented by Example 8.3.

[0194] In a further aspect, the invention relates to Examples E.1 to E.300 listed in Table E, wherein R 7 and R 8 are represented by Example 8.4.

[0195] In a further aspect, the invention relates to Examples E.1 to E.300 listed in Table E, wherein R 7 and R 8 are represented by Example 8.7.

[0196] In particular, in view of their use, according to one embodiment, it is preferred to assemble 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. Furthermore, each group mentioned for the substituents in the tables by itself (independently of the combinations mentioned) is a particularly preferred aspect of said substituents.

[0197]

[0198] Table 1a Compounds of formulae I.A-1, I.A-2, I.A-3, I.A-4, I.A-5, I.A-6, wherein R 9 is CH3, and for each individual compound the meanings of the combinations of X 1 , X 2 , R 5 , R 6 , R 7 and R 8 correspond in each case to a row in Table B (Compounds I.A-1.1a.B-1 to I.A-1.1a.B-672, I.A-2.1a.B-1 to I.A-2.1a.B-672, I.A-3.1a.B-1 to I.A-3.1a.B-672, I.A-4.1a.B-1 to I.A-4.1a.B-672, I.A-5.1a.B-1 to I.A-5.1a.B-672, I.A-6.1a.B-1 to I.A-6.1a.B-672).

[0199] Table 2a Compounds of formulae I.A-1, I.A-2, I.A-3, I.A-4, I.A-5, I.A-6, wherein R 9 is CH2CH3, and for each individual compound the meanings of the combinations of X 1 , X 2 , R 5 , R 6 , R 7 and R 8The meaning of the combination corresponds in each case to a row in Table B (compounds I.A-1.2a.B-1 to I.A-1.2a.B-672, I.A-2.2a.B-1 to I.A-2.2a.B-672, I.A-3.2a.B-1 to I.A-3.2a.B-672, I.A-4.2a.B-1 to I.A-4.2a.B-672, I.A-5.2a.B-1 to I.A-5.2a.B-672, I.A-6.2a.B-1 to I.A-6.2a.B-672).

[0200] Table 3a Compounds of formula I.A-1, I.A-2, I.A-3, I.A-4, I.A-5, I.A-6, where R 9 is CH2CH2CH3, and for each individual compound, the meaning of the combination of X 1 、X 2 、R 5 、R 6 、R 7 and R 8 corresponds in each case to a row in Table B (compounds I.A-1.3a.B-1 to I.A-1.3a.B-672, I.A-2.3a.B-1 to I.A-2.3a.B-672, I.A-3.3a.B-1 to I.A-3.3a.B-672, I.A-4.3a.B-1 to I.A-4.3a.B-672, I.A-5.3a.B-1 to I.A-5.3a.B-672, I.A-6.3a.B-1 to I.A-6.3a.B-672).

[0201] Table 4a Compounds of formula I.A-1, I.A-2, I.A-3, I.A-4, I.A-5, I.A-6, where R 9 is CN, and for each individual compound, the meaning of the combination of X 1 、X 2 、R 5 、R 6 、R 7 and R 8 corresponds in each case to a row in Table B (compounds I.A-1.4a.B-1 to I.A-1.4a.B-672, I.A-2.4a.B-1 to I.A-2.4a.B-672, I.A-3.4a.B-1 to I.A-3.4a.B-672, I.A-4.4a.B-1 to I.A-4.4a.B-672, I.A-5.4a.B-1 to I.A-5.4a.B-672, I.A-6.4a.B-1 to I.A-6.4a.B-672).

[0202] Table 5a has compounds of formulae I.A-1, I.A-2, I.A-3, I.A-4, I.A-5, I.A-6, wherein R 9 is CH2CN, and for each individual compound the meaning of the combination of X 1 , X 2 , R 5 , R 6 , R 7 and R 8 corresponds in each case to a row in Table B (compounds I.A-1.5a.B-1 to I.A-1.5a.B-672, I.A-2.5a.B-1 to I.A-2.5a.B-672, I.A-3.5a.B-1 to I.A-3.5a.B-672, I.A-4.5a.B-1 to I.A-4.5a.B-672, I.A-5.5a.B-1 to I.A-5.5a.B-672, I.A-6.5a.B-1 to I.A-6.5a.B-672)

[0203] Table 6a has compounds of formulae I.A-1, I.A-2, I.A-3, I.A-4, I.A-5, I.A-6, wherein R 9 is CHO, and for each individual compound the meaning of the combination of X 1 , X 2 , R 5 , R 6 , R 7 and R 8 corresponds in each case to a row in Table B (compounds I.A-1.6a.B-1 to I.A-1.6a.B-672, I.A-2.6a.B-1 to I.A-2.6a.B-672, I.A-3.6a.B-1 to I.A-3.6a.B-672, I.A-4.6a.B-1 to I.A-4.6a.B-672, I.A-5.6a.B-1 to I.A-5.6a.B-672, I.A-6.6a.B-1 to I.A-6.6a.B-672)

[0204] Table 7a has compounds of formulae I.A-1, I.A-2, I.A-3, I.A-4, I.A-5, I.A-6, wherein R 9 is C(CH3)3, and for each individual compound the meaning of the combination of X 1 , X 2 , R 5 , R 6 , R 7 and R 8The meaning of the combinations corresponds in each case to a row in Table B (compounds I.A-1.7a.B-1 to I.A-1.7a.B-672, I.A-2.7a.B-1 to I.A-2.7a.B-672, I.A-3.7a.B-1 to I.A-3.7a.B-672, I.A-4.7a.B-1 to I.A-5.7a.B-672, I.A-5.7a.B-1 to I.A-5.7a.B-672, I.A-6.7a.B-1 to I.A-6.7a.B-672)

[0205] Table 8a Compounds of formula I.A-1, I.A-2, I.A-3, I.A-4, I.A-5, I.A-6, where R 9 is COCH3, and for each individual compound, the meaning of the combination of X 1 、X 2 、R 5 、R 6 、R 7 and R 8 corresponds in each case to a row in Table B (compounds I.A-1.8a.B-1 to I.A-1.8a.B-672, I.A-2.8a.B-1 to I.A-2.8a.B-672, I.A-3.8a.B-1 to I.A-3.8a.B-672, I.A-4.8a.B-1 to I.A-5.8a.B-672, I.A-5.8a.B-1 to I.A-5.8a.B-672, I.A-6.8a.B-1 to I.A-6.8a.B-672)

[0206] Table 9a Compounds of formula I.A-1, I.A-2, I.A-3, I.A-4, I.A-5, I.A-6, where R 9 is CH2C(CH3)3, and for each individual compound, the meaning of the combination of X 1 、X 2 、R 5 、R 6 、R 7 and R 8 corresponds in each case to a row in Table B (compounds I.A-1.9a.B-1 to I.A-1.9a.B-672, I.A-2.9a.B-1 to I.A-2.9a.B-672, I.A-3.9a.B-1 to I.A-3.9a.B-672, I.A-4.9a.B-1 to I.A-5.9a.B-672, I.A-5.9a.B-1 to I.A-5.9a.B-672, I.A-6.9a.B-1 to I.A-6.9a.B-672)

[0207] Table 10a has compounds of formulae I.A-1, I.A-2, I.A-3, I.A-4, I.A-5, I.A-6, where R 9 is CH2CH=CH2, and for each individual compound the meanings of X 1 , X 2 , R 5 , R 6 , R 7 and R 8 in combination correspond in each case to a row in Table B (compounds I.A-1.10a.B-1 to I.A-1.10a.B-672, I.A-2.10a.B-1 to I.A-2.10a.B-672, I.A-3.10a.B-1 to I.A-3.10a.B-672, I.A-4.10a.B-1 to I.A-5.10a.B-672, I.A-5.10a.B-1 to I.A-5.10a.B-672, I.A-6.10a.B-1 to I.A-6.10a.B-672)

[0208] Table 11a has compounds of formulae I.A-1, I.A-2, I.A-3, I.A-4, I.A-5, I.A-6, where R 9 is CH2CCH, and for each individual compound the meanings of X 1 , X 2 , R 5 , R 6 , R 7 and R 8 in combination correspond in each case to a row in Table B (compounds I.A-1.11a.B-1 to I.A-1.11a.B-672, I.A-2.11a.B-1 to I.A-2.11a.B-672, I.A-3.11a.B-1 to I.A-3.11a.B-672, I.A-4.11a.B-1 to I.A-5.11a.B-672, I.A-5.11a.B-1 to I.A-5.11a.B-672, I.A-6.11a.B-1 to I.A-6.11a.B-672)

[0209] Table 12a has compounds of formulae I.A-1, I.A-2, I.A-3, I.A-4, I.A-5, I.A-6, where R 9 is CH2C6H5, and for each individual compound the meanings 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 (Compound I.A-1.12a.B-1 to I.A-1.12a.B-672, I.A-2.12a.B-1 to I.A-2.12a.B-672, I.A-3.12a.B-1 to I.A-3.12a.B-672, I.A-4.12a.B-1 to I.A-5.12a.B-672, I.A-5.12a.B-1 to I.A-5.12a.B-672, I.A-6.12a.B-1 to I.A-6.12a.B-672)

[0210] Table B

[0211]

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228] 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.

[0229] 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.

[0230]

[0231] The benzodiazepine represented by formula (2) The compound can be prepared by reacting a series of diamines represented by formula (4) (or their HCl salts) with at least one halogen (represented by X 1 Indicates that it is preferred that F) substituted quinolyl / quinoxalinyl aryl ketone (3) is prepared by reaction in the presence of a base. The reaction is preferably carried out at room temperature to 120° C. using 1 to 6 equivalents of a base and 1 to 1.5 equivalents of a diamine, similar to the methods described in WO 2016 / 87370A1, Org. Biomol. Chem. [Organic and Biomolecular Chemistry] (2014), 12, 6895-6900, WO 2006 / 44753A2, Heterocycles [Heterocycles] (1994), 38, 125-134.

[0232]

[0233] The aryl ketone (3) is commercially available or can be prepared by oxidizing the aryl alcohol (5) using, for example, manganese dioxide, as described in Inorganica Chimica Acta (2012), 382, 72 - 78, WO 2000 / 038618, CN107879989 A, or Chinese Science Bulletin 2010, 55(25), 2817 - 2819.

[0234]

[0235] The aryl alcohol (5) can be prepared by isopropylmagnesium chloride - mediated bromine / iodine - magnesium exchange of 7, and subsequent addition to the commercially available aldehyde represented by the general formula (6). This reaction is preferably carried out at 0 °C with an equimolar ratio of iPrMgCl to the aryl halide (7), and the intermediate of this aryl halide is employed at a ratio of 1.2 - 1.3:1 relative to the aldehyde (6), as described in US2010 / 41698A1, Org. Lett. (2018), 20, 138 - 141, WO 2014 / 102233 A1, or US2016 / 83401A1.

[0236]

[0237] Alternatively, the scaffold represented by formula (2) can also be obtained by reacting the aryl ketone (3) with the 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. Then, the resulting product 9 can 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. Then alkylation / acylation can be carried out as described above to obtain compound I.

[0238]

[0239] Compound I and its compositions are each suitable as fungicides, effectively against a broad spectrum of phytopathogenic fungi, including soil-borne fungi, in particular fungi from the classes Chytridiomycetes, Peronosporomycetes (synonym Oomycetes), Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes (synonym Fungi imperfecti). They can be used in crop protection as foliar fungicides, seed dressing fungicides and soil fungicides.

[0240] Compound I and its compositions are preferably useful for controlling 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, for example pomes (apples, pears, etc.), stone fruits (for example plums, peaches, almonds, cherries) or soft fruits, also known as berries (strawberries, raspberries, blackberries, currants, etc.); leguminous plants such as lentils, peas, alfalfa or soybeans; oil plants such as rape, mustard, olive, sunflower, coconut, cocoa bean, castor oil plant, oil palm, peanut or soybean; cucurbits, for example pumpkins, cucumbers or melons; fibre plants such as cotton, flax, hemp or jute; citrus fruits such as oranges, lemons, grapefruits or tangerines; vegetables such as spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, gourds or red peppers; laurel family plants such as avocado, cinnamon or camphor; energy and raw material plants such as maize, soybean, rape, sugar cane or oil palm; maize; tobacco; nuts; coffee; tea; bananas; grapevines (table grape and grape juice grapevines); hops; turf; stevia (also known as Stevia rebaudiana); natural rubber plants; or ornamental and forest plants such as flowers, shrubs, broad-leaved trees or evergreens (conifers, eucalyptus, etc.); plant propagation material such as seeds; and crop material of these plants.

[0241] More preferably, Compound I and its compositions are each used for controlling fungi on the following: field crops such as potatoes, sugar beet, tobacco, wheat, rye, barley, oats, rice, maize, cotton, soybeans, rape, beans, sunflowers, coffee or sugar cane; fruits; vines; ornamental plants; or vegetables such as cucumbers, tomatoes, green beans or pumpkins.

[0242] The term "plant propagation material" is to be understood as meaning all the generative parts of plants, such as seeds; and vegetative plant material which can be used for plant propagation, such as cuttings and tubers (such as potatoes). This includes the seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, buds and other parts of plants; including seedlings and young plants after germination or emergence which are transplanted.

[0243] Preferably, the plant propagation materials are treated with Compound I and its compositions respectively for controlling fungi on the following plants: cereals such as wheat, rye, barley and oats; rice, corn, cotton and soybeans.

[0244] 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 rapeseed, such as winter wheat, spring wheat, winter barley, etc.

[0245] Corn is also known as Indian corn or maize (maize / Zea mays), which includes all kinds of corn such as feed corn and sweet corn. According to the present invention, it includes all Zea mays or corn subspecies and / or varieties, especially flour corn (Zea mays var. amylacea), popcorn (Zea mays var. everta), dent corn (Zea mays var. indentata), flint corn (Zea mays var. indurata), sweet corn (Zea mays var. saccharata and var. rugosa), waxy corn (Zea mays var. ceratina), high amylose corn (amylomaize) (high amylose maize cultivar), pod corn or wild maize (Zea mays var. tunicata) and striped maize (Zea mays var. japonica).

[0246] 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). The indeterminate growth habit (maturity groups, MG 00 to MG 4.9) is characterized by the continuation of vegetative growth after the start of flowering, while determinate soybean cultivars (MG 5 to MG 8) characteristically have completed most of their vegetative growth at the start of flowering. According to the present invention, it includes all soybean cultivars or varieties, especially indeterminate and determinate cultivars or varieties.

[0247] 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 technology 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 genome of the plant in order to add traits or improve or modify traits. These integrated genes are also referred to as transgenes, and plants containing such transgenes are referred to as transgenic plants. The plant transformation process typically results in a number of transformation events that differ in the genomic loci where the transgenes have 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 have been modified include herbicide tolerance, insect resistance, increased yield, and tolerance to abiotic conditions such as drought.

[0248] 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.

[0249] 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.

[0250] 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.

[0251] 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.

[0252] 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.

[0253] 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).

[0254] 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).

[0255] Tolerance to abiotic conditions such as drought has been achieved by using the transgenes cspB (maize event MON87460) and Hahb-4 (soybean event ) generated.

[0256] Traits are typically combined to produce cultivated plants with 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 tolerance to Lepidoptera and Coleoptera insects, combinations of herbicide tolerance with one or several types of insect resistance, combinations of herbicide tolerance with increased yield, and combinations of herbicide tolerance and tolerance to abiotic conditions.

[0257] 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, WO13 / 003558; for cotton events MON1445, MON15985, MON531 (MON15985), LLCotton25, MON88913, COT102, 281-24-236, 3006-210-23, COT67B, GHB614, T304-40, GHB119, MON88701, 81910, can be found in WO 02 / 034946, WO 02 / 100163, WO 02 / 100163, WO 03 / 013224, WO 04 / 072235, WO 04 / 039986, WO 05 / 103266, WO 05 / 103266, WO 06 / 128573, WO 07 / 017186, WO 08 / 122406, WO 08 / 151780, WO 12 / 134808, WO 13 / 112527;For maize events GA21, MON810, DLL25, TC1507, MON863, MIR604, LY038, MON88017, 3272, 59122, NK603, MIR162, MON89034, 98140, 32138, MON87460, 5307, 4114, MON87427, DAS40278, MON87411, 33121, MON87403, MON87419, see WO 98 / 044140, US 02 / 102582, US 03 / 126634, WO 04 / 099447, WO 04 / 011601, WO 05 / 103301, WO 05 / 061720, WO 05 / 059103, WO 06 / 098952, WO 06 / 039376, US2007 / 292854, WO07 / 142840, WO 07 / 140256, WO 08 / 112019, WO 09 / 103049, WO 09 / 111263, WO 10 / 077816, WO11 / 084621, WO 11 / 062904, WO 11 / 022469, WO 13 / 169923, WO 14 / 116854, WO 15 / 053998, WO15 / 142571; for potato events E12, F10, J3, J55, V11, X17, Y9, see WO 14 / 178910, WO 14 / 178913, WO 14 / 178941, WO 14 / 179276, WO 16 / 183445, WO 17 / 062831, WO 17 / 062825; for rice events LLRICE06, LLRICE601, LLRICE62, see WO 00 / 026345, WO 00 / 026356, WO 00 / 026345;And for the soybean events H7-1, MON89788, A2704-12, A5547-127, DP305423, DP356043, MON87701, MON87769, CV127, MON87705, DAS68416-4, MON87708, MON87712, SYHT0H2, DAS81419, DAS81419 x DAS44406-6, MON87751, reference may be made to 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.;

[0258] The separate use of Compound I and its compositions on cultivated plants can result in effects specific to cultivated plants comprising a certain transgene or event. These effects may relate to altered 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 or delayed maturity, cold or heat tolerance and altered amino acid or fatty acid profiles or contents.

[0259] Compound I and its compositions are particularly suitable, respectively, for controlling the causative agents of the following plant diseases:

[0260] Species of Albugo (white rust) on ornamental plants, vegetables (e.g., A. candida), and sunflowers (e.g., A. tragopogonis); species of Alternaria (alternaria leaf spot) on vegetables (e.g., A. dauci or A. porri), rape (A. brassicola or A. brassicae), sugar beet (A. tenuis), fruits (e.g., A. grandis), rice, soybeans, potatoes, and tomatoes (e.g., A. solani, A. grandis, or A. alternata), tomatoes (e.g., A. solani or A. alternata), and wheat (e.g., A. triticina); species of Aphanomyces on sugar beet and vegetables; species of Ascochyta on cereals and vegetables, such as A. tritici on wheat (anthracnose) and A. hordei on barley; Aureobasidium zeae (synonym Kapatiella zeae) on maize; species of Bipolaris and Drechslera (teleomorph: species of Cochliobolus), such as southern leaf blight (D. maydis) or northern leaf blight (B. zeicola) on maize, such as spot blotch (B. sorokiniana) on cereals and B. oryzae on rice and turfgrass; Blumeria graminis (formerly known as Erysiphe graminis) on cereals (e.g., wheat or barley) (powdery mildew); Botrytis cinerea (teleomorph: Botryotinia fuckeliana: gray mold) on fruits and berries (e.g., strawberries), vegetables (e.g., lettuce, carrots, celery, and cabbages); Botrytis squamosa or Botrytis allii on onion family, rape, ornamental plants (e.g., B. elliptica), vines, forest plants, and wheat; Bremia lactucae on lettuce (downy mildew); species of Ceratocystis (synonym Ophiostoma) on broad-leaved and evergreen trees (rot or wilt), 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).

[0261] (formerly known as Dactylium dendroides), teleomorph: Nectria albertinii, Nectria rosella (synonym Hypomyces rosellus); Cladosporium species on tomato (e.g., C. fulvum: leaf mold) and cereals, e.g., C. herbarum on wheat (black ear); Claviceps purpurea on cereals (ergot); Cochliobolus species (anamorph: Helminthosporium of the genus Bipolaris) on maize (C. carbonum), cereals (e.g., C. sativus, anamorph: B. sorokiniana) and rice (e.g., C. miyabeanus, anamorph: H. oryzae) (leaf spot); Colletotrichum (teleomorph: Glomerella) species on cotton (e.g., C. gossypii), maize (e.g., C. graminicola: anthracnose stalk rot), soft fruits, potato (e.g., C. coccodes: black dot), bean (e.g., C. lindemuthianum), soybean (e.g., C. truncatum or C. gloeosporioides), vegetables (e.g., C. lagenarium or C. capsici), fruits (e.g., C. acutatum), coffee (e.g., C. coffeanum or C. kahawae) and various crops (C. gloeosporioides) (anthracnose); Corticium species, e.g., C. sasakii on rice (sheath blight); Corynespora cassiicola on soybean, cotton and ornamental plants (leaf spot); Cycloconium species, e.g., C. oleaginum on olive trees; fruit trees, vines (e.g., Cylindrocladiumliriodendri), sexual form: Neonectria liriodendri: Black Foot Disease) and Cylindrocarpon species on ornamental plants (such as fruit tree canker or young vine decline, sexual form: Nectria or Neonectria species); Dematophora necatrix on soybeans (sexual form: Rosellinia necatrix) (root and stem rot); Diaporthe species, such as D. phaseolorum on soybeans (damping-off); Drechslera (synonym Helminthosporium, sexual form: Pyrenophora) species on corn, cereals such as barley (e.g., D. teres, net blotch) and wheat (e.g., D. tritici-repentis: tan spot), rice and turfgrass; Esca (dieback, apoplexy) on vines, caused by Formitiporia punctata (synonym Phellinus punctata), F. mediterranea, Phaeomoniella chlamydospora (previously known as Phaeoacremonium chlamydosporum), Phaeoacremonium aleophilum and / or Botryosphaeria obtusa; Elsinoe species on pome fruits (E. pyri), soft fruits (E. veneta: anthracnose) and vines (E. ampelina: anthracnose); Entyloma oryzae on rice (leaf smut); Epicoccum species on wheat (black mold); Erysiphe betae on sugar beets, Erysiphe pisi on vegetables (such as peas) such as cucurbits (such as E. cichoracearum), cabbages, oilseeds (such as Erysiphe cruciferarum)species of Erysiphe (powdery mildew) on cruciferarum; Eutypa lata (Eutypa canker or dieback, anamorph: Cytosporina lata, synonym Libertella blepharis) on fruit trees, vines and ornamental trees; species of Exserohilum (synonym Helminthosporium) on maize (e.g., Exserohilum turcicum); species of Fusarium (teleomorph: Gibberella) on a variety of plants (wilt, root or stem rot), such as Fusarium graminearum or Fusarium culmorum (root rot, scab or head blight) on cereals (e.g., wheat or barley), Fusarium oxysporum on tomato, Fusarium solani (f.sp. glycines, new synonym Fusarium virguliforme) on soybean and F. tucumaniae and F. brasiliense (both causing sudden death syndrome), and Fusarium verticillioides on maize; Gaeumannomyces graminis (take-all) on cereals (e.g., wheat or barley) and maize; species of Gibberella on cereals (e.g., Gibberella zeae) and rice (e.g., Gibberella fujikuroi: Bakanae disease); Glomerella cingulata on vines, pome fruits and other plants and Glomerella gossypii on cotton; Grainstaining complex on rice; Guignardia bidwellii (black rot) on vines; species of Gymnosporangium on Rosaceae plants and junipers, such as Gymnosporangium sabinae (rust) on pears; species of Helminthosporium (synonym Drechslera, teleomorph: Cochliobolus) on maize, cereals, potatoes and rice; species of Hemileia, such as Hemileia vastatrix on coffeevastatrix) (coffee leaf rust); Isariopsis clavispora (synonym Cladosporium vitis) on vines; Macrophomina phaseolina (synonym Macrophomina phaseoli) (root and stem rot) on soybeans and cotton; Microdochium nivale (synonym Fusarium nivale) (pink snowmold) on cereals (e.g., wheat or barley); Microsphaera diffusa (powdery mildew) on soybeans; Monilinia species on stone fruits and other Rosaceae plants, such as M. laxa, M. fructicola, and M. fructigena (synonym Monilia species: blossom blight and twig blight, brown rot); Mycosphaerella species on cereals, bananas, soft fruits, and groundnuts, such as M. graminicola on wheat (anamorph: Zymoseptoria tritici, previously known as Septoria tritici: Septoria leaf blotch), or M. fijiensis (synonym Pseudocercospora fijiensis: black Sigatoka disease) and M. musicola on bananas, M. arachidicola (synonym M. arachidis or Cercospora arachidis) on groundnuts, M. berkeleyi, M. pisi on peas, and M. brassiciola on Brassica; Peronospora species (downy mildew) on cabbages (e.g., P. brassicae), oilseed rape (e.g., P. parasitica), onions (e.g., P. destructor), tobacco (P. tabacina), and soybeans (e.g., P. manshurica); Phakopsora pachyrhizi and P.meibomiae) (soybean rust); Phialophora species, such as on vines (e.g., P. tracheiphila and P. tetraspora) and soybeans (e.g., P. gregata: stem rot); Phoma lingam (synonyms Leptosphaeria biglobosa and L. maculans: root and stem rot) on rapeseed and cabbage and P. betae (root rot, leaf spot and damping-off) on sugar beet, and P. zeae-maydis (synonym Phyllostica zeae) on maize; Phomopsis species on sunflowers, vines (e.g., P. viticola: vine and leaf spot) and soybeans (e.g., stem rot: P. phaseoli, teleomorph: Diaporthe phaseolorum); Physoderma maydis (brown spot) on maize; Phytophthora species (wilting, root, leaf, fruit and stem rot) on various plants, such as red pepper and gourd (e.g., P. capsici), soybeans (e.g., P. megasperma, synonym P. sojae), potatoes and tomatoes (e.g., P. infestans: late blight) and broad-leaved trees (e.g., P. ramorum: sudden oak death); Plasmodiophora brassicae (club root) on cabbage, rapeseed, radish and other plants; Plasmopara species, such as P. viticola (downy mildew of grapevine) on vines and P. halstedii on sunflowers; Podosphaera species (powdery mildew) on Rosaceae plants, hops, pome and soft fruits, such as P. leucotricha on apples and P. xanthii on gourds; Polymyxa species, such as P. graminis on cereals such as barley and wheat and P. betae on sugar beet, and virus diseases transmitted thereby; Pseudocercosporella herpotrichoides (synonyms Oculimacula yallundae, O.acuformis: eye spot disease, teleomorph: Tapesia yallundae); Pseudoperonospora species (downy mildew) on various plants, e.g., Pseudoperonospora cubensis on cucurbits or Pseudoperonospora humili on hops; Pseudopezicula tracheiphila (red fire disease or rotbrenner, anamorph: Phialophora) on vines; Puccinia species (rust) on various plants, e.g., Puccinia triticina (brown rust or leaf rust) on cereals such as wheat, barley or rye, Puccinia striiformis (strip rust or yellow rust), Puccinia hordei (dwarf rust), Puccinia graminis (stem rust or black rust) or Puccinia recondita (brown rust or leaf rust), Puccinia kuehnii (citrus rust) on sugarcane and Puccinia asparagi on asparagus; Pyrenopeziza species, e.g., Pyrenopeziza brassicae on rape; Pyrenophora tritici-repentis (anamorph: Drechslera tritici-repentis) (tan spot) on wheat or Pyrenophora teres (net blotch) on barley; Pyricularia species, e.g., Pyricularia oryzae (teleomorph: Magnaporthe grisea: rice blast) on rice, and Pyricularia grisea on turfgrass and cereals; Pythium species (damping-off) (e.g., Pythium ultimum or Pythium aphanidermatum) on turfgrass, rice, maize, wheat, cotton, rape, sunflower, soybean, sugar beet, vegetables and various other plants and Pythium oligandrum on mushrooms; Ramularia species, e.g., Ramularia collo-cygni (Ramularia leaf spot, physiological leaf spot) on barley, Ramularia areola (teleomorph: Mycosphaerella areola) on cotton and Ramularia beticola on sugar beet;beticola); Rhizoctonia species on cotton, rice, potato, turfgrass, corn, rape, potato, sugar beet, vegetables, and various other plants, such as Rhizoctonia solani (root and stem rot) on soybean, Rhizoctonia solani (sheath blight) on rice, or Rhizoctonia cerealis (Rhizoctonia spring leaf blight) on wheat or barley; 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 (sheath rot) on rice; Sclerotinia species (stem rot or white mold) on vegetables (Sclerotinia minor and S. sclerotiorum) and field crops, such as rape, sunflower (e.g., Sclerotinia), and soybean; Sclerotium rolfsii (synonym Athelia rolfsii) on soybean, peanut, vegetables, corn, cereals, and ornamental plants; Septoria species on various plants, such as Septoria glycines (brown spot) on soybean, Septoria tritici (synonym Zymoseptoria tritici, Septoria leaf blotch) on wheat, and Septoria nodorum (synonym Stagonospora nodorum (Stagonospora leaf blotch)) on cereals; Uncinula necator (synonym Erysiphe necator) (powdery mildew, anamorph: Oidium tuckeri) on vine; Setosphaeria species (leaf blight) on corn (e.g., Setosphaeria turcicum, synonym Helminthosporium turcicum) and turfgrass; corn (e.g., Sphacelotheca reilianareiliana), 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, such as 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, such as Taphrina deformans on peaches (leaf curl) and Taphrina pruni on plums (plum pocket); Thielaviopsis species on tobacco, pome fruits, vegetables, soybeans and cotton (black root rot), such as Thielaviopsis basicola (synonym Chalara elegans); Tilletia species on cereals (common bunt or stinking smut), such as Tilletia tritici on wheat (synonym Tilletia caries, common bunt of wheat) and Tilletia controversa (dwarf bunt); Trichoderma harzianum on mushrooms; Typhula incarnate on barley or wheat (grey snow mold); Urocystis species, such as 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 Uromyces (rust) on fabae); species of Ustilago (loose smut) on cereals (e.g., U. nuda and U. avenae), maize (e.g., U. maydis: corn smut) and sugar cane; species of Venturia (scab) on apples (e.g., V. inaequalis) and pears; and species of Verticillium (wilt) on a variety of plants such as fruit and ornamental plants, vines, soft fruits, vegetables and field crops, e.g., V. longisporum on oilseed rape, V. dahliae on strawberries, oilseed rape, potatoes and tomatoes, and V. fungicola on mushrooms; Septoria tritici on cereals.

[0262] Compound I and its compositions are particularly suitable for controlling the pathogenic agents of the following plant diseases: rust on soybeans and cereals (e.g., Phakopsora pachyrhizi and Phakopsora meibomiae on soybeans; Puccinia triticina and Puccinia striiformis on wheat); mildew on specialty crops, soybeans, oilseed rape and sunflowers (e.g., Botrytis cinerea on strawberries and vines, Sclerotinia sclerotiorum, Sclerotinia minor and Sclerotium rolfsii on oilseed rape, sunflowers and soybeans); Fusarium diseases on cereals (e.g., Fusarium culmorum and Fusarium graminearum on wheat); downy mildew on specialty crops (e.g., Plasmopara viticola on vines, Phytophthora infestans on potatoes); powdery mildew on specialty crops and cereals (e.g., Uncinula necator on vines, species of Erysiphe on various specialty crops, Blumeria graminis on cereals); and leaf spot on cereals, soybeans and maize (e.g., Septoria tritici and Septoria nodorum on cereals, Septoria glycines on soybeans, species of Cercospora on maize and soybeans).

[0263] 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.

[0264] 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.

[0265] 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.

[0266] 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.

[0267] 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.

[0268] 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.

[0269] 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.

[0270] 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.

[0271] 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.

[0272] 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.

[0273] 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.

[0274] 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.

[0275] 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.

[0276] 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.

[0277] 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.

[0278] 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.

[0279] 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.

[0280] 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.

[0281] 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.

[0282] 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.

[0283] 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.

[0284] 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.

[0285] 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.

[0286] 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.

[0287] 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.

[0288] 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.

[0289] 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.

[0290] 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.

[0291] 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.

[0292] 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.

[0293] 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.

[0294] 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.

[0295] 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.

[0296] 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.

[0297] 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.

[0298] 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.

[0299] 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.

[0300] 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.

[0301] 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.

[0302] 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.

[0303] 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.

[0304] 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.

[0305] 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.

[0306] List Z:

[0307] Species of Albugo (white rust) on ornamental plants, vegetables (e.g., A. candida), and sunflowers (e.g., A. tragopogonis); species of Alternaria (alternaria leaf spot) on vegetables (e.g., A. dauci or A. porri), rape (A. brassicola or A. brassicae), sugar beet (A. tenuis), fruits (e.g., A. grandis), rice, soybeans, potatoes, and tomatoes (e.g., A. solani, A. grandis, or A. alternata), tomatoes (e.g., A. solani or A. alternata), and wheat (e.g., A. triticina); species of Aphanomyces on sugar beet and vegetables; species of Ascochyta on cereals and vegetables, such as A. tritici on wheat (anthracnose) and A. hordei on barley; Aureobasidium zeae (synonym Kapatiella zeae) on maize; species of Bipolaris and Drechslera (teleomorph: species of Cochliobolus), such as southern leaf blight (D. maydis) or northern leaf blight (B. zeicola) on maize, such as spot blotch (B. sorokiniana) on cereals and, for example, B. oryzae on rice and turfgrass; Blumeria graminis (formerly known as Erysiphe graminis) on cereals (e.g., wheat or barley) (powdery mildew); Botrytis cinerea (teleomorph: Botryotinia fuckeliana: gray mold) on fruits and berries (e.g., strawberries), vegetables (e.g., lettuce, carrots, celery, and cabbages); Botrytis squamosa or Botrytis allii on onion family, rape, ornamental plants (e.g., B. elliptica), vines, forest plants, and wheat; Bremia lactucae on lettuce (downy mildew); species of Ceratocystis (synonym Ophiostoma) on broad-leaved and evergreen trees (rot or wilt), 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).

[0308] (formerly known as Dactylium dendroides), teleomorph: Nectria albertinii, Nectria rosella (synonym Hypomyces rosellus); Cladosporium species on tomato (e.g., C. fulvum: leaf mold) and cereals, e.g., C. herbarum on wheat (black ear); Claviceps purpurea on cereals (ergot); Cochliobolus (anamorph: Helminthosporium of the genus Bipolaris) species on maize (C. carbonum), cereals (e.g., C. sativus, anamorph: B. sorokiniana) and rice (e.g., C. miyabeanus, anamorph: H. oryzae) (leaf spot); Colletotrichum (teleomorph: Glomerella) species on cotton (e.g., C. gossypii), maize (e.g., C. graminicola: anthracnose stalk rot), soft fruits, potato (e.g., C. coccodes: black dot), bean (e.g., C. lindemuthianum), soybean (e.g., C. truncatum or C. gloeosporioides), vegetables (e.g., C. lagenarium or C. capsici), fruits (e.g., C. acutatum), coffee (e.g., C. coffeanum or C. kahawae) and various crops (C. gloeosporioides) (anthracnose); Corticium species, e.g., C. sasakii on rice (sheath blight); Corynespora cassiicola on soybean, cotton and ornamental plants (leaf spot); Cycloconium species, e.g., C. oleaginum on olive trees; fruit trees, vines (e.g., Cylindrocladiumliriodendri), sexual form: Neonectria liriodendri: Black Foot Disease) and Cylindrocarpon species on ornamental plants (such as fruit tree canker or young vine decline, sexual form: Nectria or Neonectria species); Dematophora necatrix on soybeans (sexual form: Rosellinia necatrix) (root and stem rot); Diaporthe species, such as D. phaseolorum on soybeans (damping-off); Drechslera (synonym Helminthosporium, sexual form: Pyrenophora) species on corn, cereals such as barley (e.g., D. teres, net blotch) and wheat (e.g., D. tritici-repentis: tan spot), rice and turfgrass; Esca (dieback, apoplexy) on vines, caused by Formitiporia punctata (synonym Phellinus punctata), F. mediterranea, Phaeomoniella chlamydospora (previously known as Phaeoacremonium chlamydosporum), Phaeoacremonium aleophilum and / or Botryosphaeria obtusa; Elsinoe species on pome fruits (E. pyri), soft fruits (E. veneta: anthracnose) and vines (E. ampelina: anthracnose); Entyloma oryzae on rice (leaf smut); Epicoccum species on wheat (black mold); Erysiphe betae on sugar beet, Erysiphe species on vegetables (such as E. pisi on peas) such as cucurbits (such as E. cichoracearum on cucumbers), cabbages, oilseeds (such as E. cruciferarum on rape)species of Erysiphe (powdery mildew) on cruciferarum)); Eutypa lata (Eutypa canker or dieback, anamorph: Cytosporina lata, synonym Libertella blepharis) on fruit trees, vines and ornamental trees; species of Exserohilum (synonym Helminthosporium) on maize (e.g., E. turcicum); species of Fusarium (teleomorph: Gibberella) on various plants (wilt, root or stem rot), such as F. graminearum or F. culmorum (root rot, scab or head blight) on cereals (e.g., wheat or barley), F. oxysporum on tomato, F. solani (f.sp. glycines, new synonym F. virguliforme) on soybean and F. tucumaniae and F. brasiliense (both causing sudden death syndrome), and F. verticillioides on maize; Gaeumannomyces graminis (take-all) on cereals (e.g., wheat or barley) and maize; species of Gibberella on cereals (e.g., G. zeae) and rice (e.g., G. fujikuroi: Bakanae disease); Glomerella cingulata on vines, pome fruits and other plants and G. gossypii on cotton; Grainstaining complex on rice; Guignardia bidwellii (black rot) on vines; species of Gymnosporangium on Rosaceae plants and junipers, such as G. sabinae (rust) on pears; species of Helminthosporium (synonym Drechslera, teleomorph: Cochliobolus) on maize, cereals, potatoes and rice; species of Hemileia, such as H. vastatrix on coffeevastatrix) (coffee leaf rust); Isariopsis clavispora (synonym Cladosporium vitis) on vines; Macrophomina phaseolina (synonym Macrophomina phaseoli) (root and stem rot) on soybeans and cotton; Microdochium nivale (synonym Fusarium nivale) (pink snowmold) 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; Peronospora species (downy mildew) on cabbages (e.g., Peronospora brassicae), oilseed rape (e.g., Peronospora parasitica), onions (e.g., Peronospora destructor), tobacco (Peronospora tabacina), and soybeans (e.g., Peronospora manshurica); Phakopsora pachyrhizi and Phakopsora sp. on soybeansmeibomiae) (soybean rust); Phialophora species, such as on vines (e.g., P. tracheiphila and P. tetraspora) and soybeans (e.g., P. gregata: stem rot); Phoma lingam (synonyms Leptosphaeria biglobosa and L. maculans: root and stem rot) on rapeseed and cabbage and P. betae (root rot, leaf spot, and damping-off) on sugar beet, and P. zeae-maydis (synonym Phyllostica zeae) on corn; Phomopsis species on sunflowers, vines (e.g., P. viticola: vine and leaf spot) and soybeans (e.g., stem rot: P. phaseoli, teleomorph: Diaporthe phaseolorum); Physoderma maydis (brown spot) on corn; Phytophthora species (wilting, root, leaf, fruit, and stem rot) on various plants, such as red peppers and gourds (e.g., P. capsici), soybeans (e.g., P. megasperma, synonym P. sojae), potatoes and tomatoes (e.g., P. infestans: late blight), and broad-leaved trees (e.g., P. ramorum: sudden oak death); Plasmodiophora brassicae (club root) on cabbage, rapeseed, radish, and other plants; Plasmopara species, such as P. viticola (downy mildew of grapevine) on vines and P. halstedii on sunflowers; Podosphaera species (powdery mildew) on Rosaceae plants, hops, pome fruits, and soft fruits, such as P. leucotricha on apples and P. xanthii on gourds; Polymyxa species, such as P. graminis on cereals such as barley and wheat and P. betae on sugar beet, and virus diseases transmitted thereby; Pseudocercosporella herpotrichoides (synonyms Oculimacula yallundae, O.acuformis: eyespot disease, teleomorph: Tapesia yallundae); Pseudoperonospora (downy mildew) on various plants, e.g., Pseudoperonospora cubensis on cucurbits or Pseudoperonospora humili on hops; Pseudopezicula tracheiphila (red fire disease or rotbrenner, anamorph: Phialophora) on vines; Puccinia species (rust) on various plants, e.g., Puccinia triticina (brown rust or leaf rust) on cereals such as wheat, barley or rye, Puccinia striiformis (stripe rust or yellow rust), Puccinia hordei (dwarf rust), Puccinia graminis (stem rust or black rust) or Puccinia recondita (brown rust or leaf rust), Puccinia kuehnii (citrus rust) on sugarcane and Puccinia asparagi on asparagus; Pyrenopeziza species, e.g., Pyrenopeziza brassicae on rape; Pyrenophora tritici-repentis (anamorph: Drechslera tritici-repentis) (tan spot) on wheat or Pyrenophora teres (net blotch) on barley; Pyricularia species, e.g., Pyricularia oryzae (teleomorph: Magnaporthe grisea: rice blast) on rice, and Pyricularia grisea on turfgrass and cereals; Pythium species (damping-off) (e.g., Pythium ultimum or Pythium aphanidermatum) on turfgrass, rice, maize, wheat, cotton, rape, sunflower, soybean, sugar beet, vegetables and various other plants and Pythium oligandrum on mushrooms; Ramularia species, e.g., Ramularia collo-cygni (Ramularia leaf spot, physiological leaf spot) on barley, Ramularia areola (teleomorph: Mycosphaerella areola) on cotton and Ramularia beticola on sugar beet;beticola); Rhizoctonia species on cotton, rice, potato, turfgrass, corn, rapeseed, potato, sugar beet, vegetables and many other plants, such as Rhizoctonia solani (root and stem rot) on soybean, Rhizoctonia solani (sheath blight) on rice, or Rhizoctonia cerealis (Rhizoctonia spring leaf blight) on wheat or barley; 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 (sheath rot) on rice; Sclerotinia species (stem rot or white mold) on vegetables (Sclerotinia minor and Sclerotinia sclerotiorum) and field crops, such as rapeseed, sunflower (e.g., Sclerotinia) and soybean; Sclerotium rolfsii (synonym Athelia rolfsii) on soybean, peanut, vegetables, corn, cereals and ornamental plants; Septoria species on many plants, such as Septoria glycines (brown spot) on soybean, Septoria tritici (synonym Zymoseptoria tritici, Septoria leaf blotch) on wheat, and Septoria nodorum (synonym Stagonospora nodorum (Stagonospora leaf blotch)) on cereals; Uncinula necator (synonym Erysiphe necator) (powdery mildew, anamorph: Oidium tuckeri) on vine; Setosphaeria species (leaf blight) on corn (e.g., Setosphaeria turcicum, synonym Helminthosporium turcicum) and turfgrass; corn (e.g., Sphacelotheca reiliana)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, such as 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, such as Taphrina deformans on peaches (leaf curl) and Taphrina pruni on plums (plum pocket); Thielaviopsis species on tobacco, pome fruits, vegetables, soybeans and cotton (black root rot), such as Thielaviopsis basicola (synonym Chalara elegans); Tilletia species on cereals (common bunt or stinking smut), such as Tilletia tritici on wheat (synonym Tilletia caries, common bunt of wheat) and Tilletia controversa (dwarf bunt); Trichoderma harzianum on mushrooms; Typhula incarnata on barley or wheat (grey snow mold); Urocystis species, such as Urocystis occulta on rye (stem smut); 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 oilseed rape, V. dahliae on strawberries, oilseed rape, potatoes and tomatoes, and V. fungicola on mushrooms; Septoria tritici on cereals.

[0309] Compound I and its compositions are also suitable for controlling harmful microorganisms in the protection of stored products or harvested materials and in the protection of materials, respectively.

[0310] The term "stored products or harvested materials" 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, shredded, ground, 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 products" should be understood to mean natural substances of plant origin and their processed forms, more preferably fruits and their processed forms, such as pome fruits, stone fruits, soft fruits and citrus fruits and their processed forms, where the application of Compound I and its compositions can also prevent adverse effects such as decay, discoloration or mould.

[0311] 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 destruction by harmful microorganisms such as fungi and bacteria.

[0312] When used in the protection of materials or stored products, the amount of the 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.

[0313] 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.

[0314] 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 the plant health condition determined above may be interdependent or may influence each other.

[0315] Compound I is used as such or in the form of a composition by treating fungi, plants, plant propagation materials (such as seeds), soil, surfaces, materials, or rooms to be protected from fungal attack with a fungicidally effective amount of the active substance. The application can be carried out before and after the plants, plant propagation materials (such as seeds), soil, surfaces, materials, or rooms are infected with fungi.

[0316] 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 harvests, or the protection of materials, and that does not cause substantial damage to the treated plants, treated stored products or harvests, 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, harvests, or materials to be treated, climatic conditions, and the specific Compound I used.

[0317] 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.

[0318] 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.

[0319] 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).

[0320] The user generally applies the agrochemical composition by means of a pre-metering device, a knapsack sprayer, a spray tank, a spraying aircraft, or an irrigation system. Generally, the agrochemical composition is made up with water, buffer, and / or additional 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.

[0321] 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 articles (e.g., LN), and gel formulations (e.g., GF) for treating plant propagation materials such as seeds. These compositions are prepared in a known manner, such as described by: Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005. The present invention also relates to agrochemical compositions comprising adjuvants and at least one compound I.

[0322] 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.

[0323] Suitable solvents and liquid carriers are water and organic solvents such as medium to high boiling mineral oil fractions like kerosene and diesel; 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.

[0324] 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.

[0325] Suitable surfactants are surface-active compounds such as anionic, cationic, non-ionic 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).

[0326] Suitable anionic surfactants are alkali metal salts, alkaline earth metal salts or ammonium salts of sulfonates, sulfates, phosphates, carboxylates and mixtures thereof. Examples of sulfonates are alkylaryl sulfonates, diphenyl sulfonates, α-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecylbenzene and tridecylbenzene, sulfonates of naphthalene and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids, oils, ethoxylated alkylphenols, alcohols, ethoxylated alcohols or fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates and carboxylated alcohol or alkylphenol ethoxylates.

[0327] Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, glycosyl surfactants, polymeric surfactants and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters that have been alkoxylated with 1 to 50 equivalents of alkylene oxide. Ethylene oxide and / or propylene oxide can be used for alkoxylation, preferably ethylene oxide. Examples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerides or glycerol monoesters. Examples of glycosyl surfactants are sorbitan, ethoxylated sorbitan, sucrose and glucose esters or alkyl polyglucosides. Examples of polymeric surfactants are homologues or copolymers of vinylpyrrolidone, vinyl alcohol or vinyl acetate.

[0328] Suitable cationic surfactants are quaternary ammonium surfactants, such as quaternary ammonium compounds having one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkyl betaines and imidazolines. Suitable block polymers are A-B or A-B-A type block polymers containing polyethylene oxide and polypropylene oxide blocks, or A-B-C type block polymers containing alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are polyacrylic acid or alkali metal salts of polyacid comb polymers. Examples of polybases are polyvinylamine or polyethylenamine.

[0329] Suitable adjuvants are compounds which themselves have negligible or even no pesticidal activity and which can enhance the biological properties of compound I against the target. Examples are surfactants, mineral oils or vegetable oils and other adjuvants. Further examples are listed in Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.

[0330] Suitable thickeners are polysaccharides (such as xanthan gum, carboxymethyl cellulose), inorganic clays (organically modified or unmodified), polycarboxylates and silicates.

[0331] Suitable fungicides are bronopol and isothiazolone derivatives, such as alkyl isothiazolones and benzisothiazolones.

[0332] Suitable antifreezes are ethylene glycol, propylene glycol, urea and glycerol.

[0333] Suitable defoamers are silicones, salts of long-chain alcohols and fatty acids.

[0334] 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).

[0335] Suitable tackifiers or binders are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, polyacrylates, biological waxes or synthetic waxes, and cellulose ethers.

[0336] Agrochemical compositions generally comprise from 0.01% to 95% by weight, preferably from 0.1% to 90% by weight, more preferably from 1% to 70% by weight, and in particular from 10% to 60% by weight of an active substance (such as at least one compound I). Agrochemical compositions generally comprise from 5% to 99.9% by weight, preferably from 10% to 99.9% by weight, more preferably from 30% to 99% by weight, and in particular from 40% to 90% by weight of at least one adjuvant. The active substance (such as compound I) is employed with a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectra).

[0337] For the purpose of treating plant propagation material, in particular seeds, seed treatment solutions (LS), suspension emulsions (SE), flowable concentrates (FS), dry treatment powders (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are generally used. After dilution 2 to 10 times, the concentration of the active substance in the ready-to-use preparation of the composition in question is from 0.01% to 60% by weight, preferably from 0.1% to 40% by weight. Application can be carried out before or during sowing. Methods for applying compound I and its compositions to plant propagation material, in particular seeds, respectively, include mixing, coating, granulating, dusting, soaking and in-furrow application methods. Preferably, compound I or its composition is applied to plant propagation material separately by a method that does not induce germination, such as by seed dressing, granulating, coating and dusting.

[0338] 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 just 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.

[0339] 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.

[0340] 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:

[0341] (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.

[0342] (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.

[0343] 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.

[0344] 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:

[0345] A) A) Respiratory inhibitors

[0346] - At Q o Complex III inhibitors at the Q-site: azoxystrobin (A.1.1), cacoxystrobin (A.1.2), coumethoxystrobin (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), fenamidone (A.1.21), fenamidone (A.1.21), methyl-N-[2-[(1,4-dimethyl-5-phenyl-pyrazol-3-yl)oxymethyl]phenyl]-N-methoxy-carbamate (A.1.22), tetraconazole (A.1.25), (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (A.1.34), (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (A.1.35), pyridaben (A.1.36), pyflubumide (A.1.37), methyl 2-(o-((2,5-dimethylphenyl-oxymethylene)phenyl)-3-methoxyacrylate (A.1.38);

[0347] - 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);

[0348] - Complex II inhibitors: carboxin (A.3.1), benzovindiflupyr (A.3.2), bixafen (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), fuberidazole (A.3.10), isofetamid (A.3.11), isopyrazam (A.3.12), triticonazole (A.3.13), oxycarboxin oxide (A.3.14), sedaxane (A.3.15), pydiflumetofen (A.3.16), penflufen (A.3.17), fluxametamide (A.3.18), fluxazolamide (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-trimethyl-4,7-dihydro-1H-inden-4-yl)nicotinamide (A.3.32), 2-(difluoromethyl)-N-[(3R)-1,1,3-trimethyl-4,7-dihydro-1H-inden-4-yl]nicotinamide (A.3.33), 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-4,7-dihydro-1H-inden-4-yl)nicotinamide (A.3.34), 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-4,7-dihydro-1H-inden-4-yl]nicotinamide (A.3.35), 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-4,7-dihydro-1H-inden-4-yl)nicotinamide (A.3.36), 2-(difluoromethyl)-N-[(3R)-1,1-dimethyl-3-propyl-4,7-dihydro-1H-inden-4-yl]nicotinamide (A.3.37), 2-(difluoromethyl)-N-(3-isobutyl-1,1-dimethyl-4,7-dihydro-1H-inden-4-yl)nicotinamide (A.3.38), 2-(difluoromethyl)-N-[(3R)-3-isobutyl-1,1-dimethyl-4,7-dihydro-1H-inden-4-yl]nicotinamide (A.3.39), triflumizole (A.3.24);

[0349] - Other respiratory inhibitors: diflufenican (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);

[0350] B) Sterol biosynthesis inhibitors (SBI fungicides)

[0351] -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-(1H-1,2,4-triazol-1-yl)-1-[5-[4-(2,2,2-trifluoroethoxy)phenyl]-2-pyridinyl]propan-2-ol (B.1.31), 2-(2,4-difluorophenyl)-1,1-difluoro-3-(1H-1,2,4-triazol-1-yl)-1-[5-[4-(trifluoromethoxy)phenyl]-2-pyridinyl]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), piperalin (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]-(pyridin-3-yl)methanol (B.1.52), 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridinyl]oxy]benzonitrile (B.1.53), 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridinyl]-1-(1,2,4-triazol-1-yl)propan-2-ol (B.1.54), 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridinyl]-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);

[0352] - 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);

[0353] - 3-ketoreductase inhibitors: fenhexamid (B.3.1);

[0354] - Other sterol biosynthesis inhibitors: etaconazole (B.4.1);

[0355] C) Nucleic acid synthesis inhibitors

[0356] - 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);

[0357] - 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);

[0358] D) Cell division and cytoskeleton inhibitors

[0359] - 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-methylthioacetamide (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-methoxyacetamide (D.1.11), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-propylbutanamide (D.1.12), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methoxy-N-propylacetamide (D.1.13), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methylthio-N-propylacetamide (D.1.14), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)-2-methylthioacetamide (D.1.15), 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-2,5-dimethylpyrazol-3-amine (D.1.16);

[0360] - Other cell division inhibitors: diethofencarb (D.2.1), ethaboxam (D.2.2), fenfuram (D.2.3), fluopicolide (D.2.4), zoxamide (D.2.5), metrafenone (D.2.6), pyriofenone (D.2.7), cyanotilide (D.2.8);

[0361] E) Amino acid and protein synthesis inhibitors

[0362] - Methionine synthesis inhibitors: cyprodinil (E.1.1), fenarimol (E.1.2), pyrimethanil (E.1.3);

[0363] - Protein synthesis inhibitors: blastcidin-S (E.2.1), kasugamycin (E.2.2), kasugamycin hydrochloride hydrate (E.2.3), validamycin (E.2.4), streptomycin (E.2.5), oxytetracycline (E.2.6);

[0364] F) Signal transduction inhibitors

[0365] - MAP / Histidine Kinase Inhibitors: fluoroimid (F.1.1), iprodione (F.1.2), procymidone (F.1.3), vinclozolin (F.1.4), fludioxonil (F.1.5);

[0366] - G-Protein Inhibitors: quinoxyfen (F.2.1);

[0367] G) Lipid and Membrane Synthesis Inhibitors

[0368] - Phospholipid Biosynthesis Inhibitors: edifenphos (G.1.1), isoprothiolane (G.1.2), pyrazophos (G.1.3), isoprobenfos (G.1.4);

[0369] - 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);

[0370] - 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);

[0371] - Compounds Affecting Cell Membrane Permeability and Fatty Acids: propamocarb (G.4.1);

[0372] Oxysterol-binding protein inhibitors: flutriafol (G.5.1), fluoxapiprolin (G.5.3), 4-[1-[2-[3-difluoromethyl-5-methyl-pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphthalen-1-yl-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);

[0373] H) Inhibitors with multi-site action

[0374] - 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);

[0375] - Thio- and dithiocarbamates: ferbam (H.2.1), mancozeb (H.2.2), maneb (H.2.3), metam sodium (H.2.4), metiram (H.2.5), zinc methyldithiocarbamate (H.2.6), thiram (H.2.7), zinc dithiocarbamate (H.2.8), zinc dimethyldithiocarbamate (H.2.9);

[0376] - 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);

[0377] - 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), bismerthiazol (H.4.8), dithianon (H.4.9), 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetrone (H.4.10);

[0378] I) Cell wall synthesis inhibitors

[0379] - Glucan synthesis inhibitors: validamycin (I.1.1), polyoxin (I.1.2);

[0380] - Melanin synthesis inhibitors: pyroquilon (I.2.1), tricyclazole (I.2.2), carpropamid (I.2.3), dicyclomet (I.2.4), probenazole (I.2.5);

[0381] J) Plant defense inducers

[0382] - Ben-S-methyl arsonate (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);

[0383] K) Unknown mode of action

[0384] -Bronopol (K.1.1), chinomethionat (K.1.2), cyflufenamid (K.1.3), cymoxanil (K.1.4), dazomet (K.1.5), iminoctadine (K.1.6), diclocymet (K.1.7), pyridinitril (K.1.8), barban (K.1.9), barban-methylsulfate (K.1.10), diphenylamine (K.1.11), cloethocarb (K.1.12), amisulbrom (K.1.13), flumetover (K.1.14), flumetylsulforim (K.1.60), sulfanilamide (K.1.15), fluopyram (K.1.16), harpin protein (K.1.17), sulfotep (K.1.18), 3,5,6-trichloro-2-pyridinol (K.1.19), phthalide (K.1.20), tolprocarb (K.1.21), copper 8-hydroxyquinoline (K.1.22), propoxyquinoline (K.1.23), seboctylamine (K.1.61), tebufloquin (K.1.24), phthalylide (K.1.25), pyrazophos (K.1.26), N'-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl-formamidine (K.1.27), N'-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methyl-formamidine (K.1.28), N'-[4-[[3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl]oxy]-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine (K.1.29), N'-(5-bromo-6-indan-2-yloxy-2-methyl-3-pyridyl)-N-ethyl-N-methyl-formamidine (K.1.30), N'-[5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.31), N'-[5-bromo-6-(4-isopropylcyclohexyloxy)-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.32), N'-[5-bromo-2-methyl-6-(1-phenylethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.33), N'-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilyl-propoxy)phenyl)-N-ethyl-N-methyl-formamidine (K.1.34), N'-(5-difluoromethyl-2-methyl-4-(3-trimethylsilyl-propoxy)phenyl)-N-ethyl-N-methyl-formamidine (K.1.35), 2-(4-chlorophenyl)-N-[4-(3,4-dimethoxyphenyl)isoxazol-5-yl]-2-prop-2-ynyloxy-acetamide (K.1.36), 3-[5-(4-chlorophenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine (picoxystrobin) (K.1.37), 3-[5-(4-methylphenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine (K.1.38), 5-chloro-1-(4,6-dimethoxypyrimidin-2-yl)-2-methyl-1H-benzimidazole (K.1.39), (Z)-ethyl 3-amino-2-cyano-3-phenylacrylate (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), thiabendazole (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-yloxy)-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);.

[0385] L) Biopesticides

[0386] 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 solisalsi, Bacillus subtilis, Bacillus subtilis var. amyloliquefaciens, Bacillus velezensis, Candida oleophila, Candida saitoana, Clavibacter michiganensis (phage), Coniothyrium minitans, Cryptocline parasitica, Cryptococcus albidus, Dilophosphora alopecuri, Fusarium oxysporum, Clonostachys rosea f. catenulate (also known as Gliocladium catenulatum), Gliocladium roseum, Lysobacter antibioticus, Lysobacter enzymogenes, Metschnikowia fructicola, Microdochium dimerum, Mycosphaerella sphaerosperma, 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);

[0387] L2) Biochemical pest control agents with fungicidal, bactericidal, virucidal and / or plant defense activator activities: harpin proteins, Reynoutria japonica Houtt. extract;

[0388] 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 nishizawae, Pasteuria penetrans, Pasteuria ramosa, Pasteuria thornei, Pasteuria usgae, Pseudomonas fluorescens, Spodoptera litura nucleopolyhedrovirus (SpliNPV), Steinernema carpocapsae, Steinernema feltiae, Streblocera nematodes, Streptomyces gilvosporeus, Streptomyces microflavus;

[0389] 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, ethyl (E,Z)-2,4-decadienoate (pear ester), (Z,Z,E)-7,11,13-hexadecatrienal, heptyl butyrate, isopropyl myristate, lavandulyl senecioate, cis-jasmone, 2-methyl-1-butanol, methyleugenol, methyl jasmonate, (E,Z)-2,13-octadecadien-1-ol, (E,Z)-2,13-octadecadien-1-yl acetate, (E,Z)-3,13-octadecadien-1-ol, (R)-1-octen-3-ol, termite pheromone (pentatermanone), (E,Z,Z)-3,8,11-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;

[0390] 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 phaseoli, Rhizobium leguminosarum biovar trifolii, Rhizobium leguminosarum biovar viciae, Rhizobium tropici, Sinorhizobium meliloti;

[0391] O) Insecticides from classes O.1 to O.29

[0392] O.1 Acetylcholinesterase (AChE) inhibitors: aldicarb, alanycarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, XMC, xylylcarb, triazamate; acephate, azamethiphos, chlorthiophos, coumaphos, crotoxyphos, dichlorvos / DDVP, dimethoate, ethion, EPN, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isopropylamine phosphate, isopropyl O-(methoxyaminothiophosphoryl) salicylate, isoxathion, malathion, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propargite, pyraclofos, pyridaphenthion, quinalphos, sulprofos, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, vamidothion;

[0393] O.2 GABA-gated chloride channel antagonists: endosulfan, chlordane; ethiprole, fipronil, ethiprole, pyrafluprole, pyriprole;

[0394] O.3 Sodium channel modulators: acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, k-bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl, 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, flumethrin, tau-fluvalinate, flubrocythrinate, heptaflumethrin, imiprothrin, metofluthrin, metofluthrin, epsilon-methoxychlor, permethrin, phenothrin, propargite, propalphos, pyrethrum, resmethrin, silafluofen, heptafluthrin, k-heptafluthrin, tetraflurothrin, tetramethrin, tetrabromomethrin, tetrafluphenthrin; DDT, methoxychlor;

[0395] 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;

[0396] O.5 Allosteric activators of nicotinic acetylcholine receptors: spinosad, spinetoram;

[0397] O.6 Chloride channel activators: abamectin, emamectin benzoate, ivermectin, lepimectin, milbemectin;

[0398] O.7 Juvenile hormone mimics: hydroprene, kinoprene, methoprene; fenoxycarb, pyriproxyfen;

[0399] O.8 Various non-specific (multi-site) inhibitors: methyl bromide and other alkyl halides; chloropicrin, sulfuryl fluoride, borax, tartar emetic;

[0400] O.9 Chordotonal organ TRPV channel modulators: cyantraniliprole, pymetrozine, flupyrimin;

[0401] O.10 Mite growth inhibitors: clofentezine, hexythiazox, flufenzine; etoxazole;

[0402] 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;

[0403] O.12 Mitochondrial ATP synthase inhibitors: diafenthiuron; azocyclotin, cyhexatin, fenbutatin oxide, propargite, tetradifon;

[0404] O.13 Oxidative phosphorylation uncouplers that interfere via the proton gradient: chlorfenapyr, DNOC, sulfluramid;

[0405] O.14 Nicotinic acetylcholine receptor (nAChR) channel blockers: bensultap, cartap, thiosultap-sodium, bisultap;

[0406] O.15 Chitin biosynthesis inhibitor type 0: bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron;

[0407] O.16 Chitin biosynthesis inhibitor type 1: buprofezin;

[0408] O.17 Molting disruptors: cyromazine;

[0409] O.18 Ecdysone receptor agonists: methoxyfenozide, tebufenozide, halofenozide, furanfenozide, chromafenozide;

[0410] O.19 Octopamine receptor agonists: amitraz;

[0411] O.20 Mitochondrial complex III electron transport inhibitors: hydramethylnon, acequinocyl, fluacrypyrim, bifenazate;

[0412] O.21 Mitochondrial complex I electron transport inhibitors: fenazaquin, flubenzimine, pyridaben, pyrimidifen, tolfenpyrad, flufenerim; rotenone;

[0413] 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;

[0414] O.23 Acetyl-CoA carboxylase inhibitors: spirodiclofen, spiromesifen, spirotetramat, methoprene, spirodiclofen + spirotetramat, 11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxo-9-aza-dispiro[4.2.4.2]tetradec-11-en-10-one, dispirotetramat;

[0415] O.24 Mitochondrial complex IV electron transport inhibitors: aluminium phosphide, calcium phosphide, phosphine, zinc phosphide, cyanide;

[0416] O.25 Mitochondrial complex II electron transport inhibitors: cyenopyrafen, butylpyridaben, etoxazole, pyraclostrobin;

[0417] 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-sulfinyl)carbamoyl]phenyl]-2-(3-chloropyridin-2-yl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[4-chloro-2-[(diethyl-λ4-sulfinyl)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;

[0418] O.29 Chordotonal organ regulator: flonicamid;

[0419] O.30 GABA-gated chloride channel allosteric modulators: broflanilide, chlorantraniliprole, isoxazid;

[0420] O.33 Calcium-activated potassium channel regulator: acynonapyr;

[0421] O.34 Mitochondrial complex III electron transport inhibitor at the Qi site: flometoquin;

[0422] O.UN Insecticidal compounds with unknown or uncertain mode of action: afoxolaner, azadirachtin, amidoflumet, bromopropylate, chlorbromuron, chinomethionat, cryolite, cyproflanilid, dichlorothymid, dicofol, flubendiamide, 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]dec-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, Bacillus firmus-based active substance (Votivo, I-1582); flutriafol; 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-pyridyl)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, Cyazypyr; 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.,

[0423] 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. 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; DE10021412; DE 102005009458; US 3,296,272; 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.;

[0424] According to the 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, after drying or evaporating the extraction or suspension medium in the case of a liquid formulation of a microbial pesticide). 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.

[0425] 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.

[0426] In a binary mixture, the weight ratio of component 1) to component 2) generally depends on the properties of the components used, and is generally in the range 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.

[0427] In a ternary mixture, i.e., a composition comprising component 1) and component 2) and compound III (component 3), the weight ratio of component 1) to component 2) depends on the properties of the active substances used, and is generally in the range 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 generally 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 component is added to component 1) in a ratio of 20:1 to 1:20. These ratios are also suitable for mixtures applied by seed treatment.

[0428] 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 carpocapsae), 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 live stage, preferably in the non-reproductive (infetive) larval stage) / ha.

[0429] 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.

[0430] 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).

[0431] Also preferred is a mixture comprising at least one active substance as component 2), said at least one active substance being selected from the complex III inhibitors 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).

[0432] Also preferred is a mixture comprising at least one active substance as component 2), said at least one active substance being selected from the complex II inhibitors 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).

[0433] 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).

[0434] 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).

[0435] 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).

[0436] 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).

[0437] 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).

[0438] 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).

[0439] 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).

[0440] 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).

[0441] 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).

[0442] 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).

[0443] 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).

[0444] 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).

[0445] Also preferably, a mixture comprising at least one active substance as component 2), which at least one active substance is selected from group K), more preferably selected from compounds (K.1.41), (K.1.42), (K.1.44), (K.1.47), (K.1.57), (K.1.58) and (K.1.59); particularly selected from (K.1.41), (K.1.44), (K.1.47), (K.1.57), (K.1.58) and (K.1.59).

[0446] 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.

[0447] Microbial biopesticides, especially those from groups L1), L3) and L5), include not only isolated pure cultures of the corresponding microorganisms as defined herein, but also their cell-free extracts, their suspensions in whole broth cultures and media containing metabolites, or purified metabolites obtained from whole broth cultures of the microorganisms.

[0448] Many of these biopesticides are deposited under the accession numbers mentioned herein (prefixes such as ATCC or DSM refer to the initials of the corresponding culture depositories, for details see, for example, http: / / www.wfcc.info / ccinfo / collection / by_acronym / ), are mentioned in the literature, are registered and / or are commercially available: the mixture of Aureobasidium pullulans DSM14940 and DSM 14941 was isolated in 1989 in Konstanz, Germany (e.g., blastospores, from ) of bio-ferm GmbH, Austria), Azospirillum brasilense Sp245 was initially isolated at least before 1980 in the wheat area of southern Brazil (Passo Fundo) (BR 11005; e.g., from Gramíneas), Azospirillum brasilense strains Ab-V5 and Ab-V6 (e.g., AzoMax from Novozymes BioAg Produtos papra Agricultura Ltda., Quartelúbalas, Brazil, or PlantSoil 331, 413-425, 2010), Bacillus amyloliquefaciens strain AP-188 (NRRL B-50615 and B-50331; US 8,445,255); Bacillus amyloliquefaciens subsp. plantarum strains, sometimes formerly also called Bacillus subtilis, recently classified together with Bacillus methylotrophicus and Bacillus velezensis as Bacillus velezensis (Int. J. Syst. Evol. Microbiol. [International Journal of Systematic and Evolutionary Microbiology] 66, 1212–1217, 2016); Bacillus amyloliquefaciens subsp. plantarum or Bacillus velezensis D747 isolated from the air in Kikugawa, Japan (US20130236522 A1; FERM BP-8234; e.g., Double Nickel TM 55WDG from Certis LLC, USA), Bacillus amyloliquefaciens subsp. plantarum or Bacillus velezensis FZB24 isolated from soil in Brandenburg, Germany (also called SB3615; DSM 96-2; J. Plant Dis. Prot. [Journal of Plant Diseases and Protection] 105, 181-197, 1998; e.g., ) from Novozyme Biologicals, Inc., USA), Bacillus amyloliquefaciens subsp. plantarum or Bacillus velezensis FZB42 isolated from soil in Brandenburg, Germany (DSM 23117; J. Plant Dis. Prot. [Journal of Plant Diseases and Protection] 105, 181-197, 1998; e.g., 42) from AbiTEP GmbH, Germany), Bacillus amyloliquefaciens subsp. plantarum or Bacillus velezensis MBI600 (also called 1430; NRRL B-50595; US2012 / 0149571A1) isolated from broad beans in Sutton Bonington, Nottinghamshire, UK at least before 1988; e.g., ) from BASF Corporation, USA), Bacillus amyloliquefaciens subsp. plantarum or Bacillus velezensis QST-713 (NRRL B-21661) isolated from a peach orchard in California, USA in 1995; e.g., MAX), Bacillus amyloliquefaciens subsp. plantarum or Bacillus velezensis TJ1000 (also known as 1BE; ATCC BAA-390; CA 2471555 A1; e.g., QuickRoots from TJ Technologies, Watertown, South Dakota, USA TM ); Bacillus firmus CNCM I-1582, a variant of the parental strain EIP-N1 isolated from soil in the central region of Israel (CNCM I-1556) (WO 2009 / 126473, US 6,406,690; e.g., from Bayer CropScience LP, USA ), Bacillus pumilus GHA 180 isolated from apple rhizosphere in Mexico (IDAC 260707-01; e.g., from Premier Horticulture, Quebec, Canada BX), Bacillus pumilus INR-7, also known as BU-F22 and BU-F33, isolated from cucumber plants infected with Erwinia tracheiphila at least prior to 1993 (NRRL B-50185, NRRL B-50153; US 8,445,255), Bacillus pumilus KFP9F isolated from grass rhizosphere 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 QST 2808 isolated from soil collected in Pohnpei, Federated States of Micronesia in 1998 (NRRL B-30087; e.g., from Bayer CropScience, USA or Plus), Bacillus simplex ABU 288 (NRRL B - 50304; US 8,445,255), also known as UD 1022 or UD10 - 22, Bacillus subtilis FB17 was isolated from red beetroot in North America (ATCC PTA - 11857; System.Appl.Microbiol. [System and Applied Microbiology] 27, 372 - 379, 2004; US2010 / 0260735; WO 2011 / 109395); Bacillus thuringiensis subsp. aizawai ABTS - 1857 was isolated in 1987 from soil taken from a lawn in Ephraim, Wisconsin, USA (also known as ABG - 6346; ATCC SD - 1372; e.g., ), Bacillus thuringiensis subsp. kurstaki ABTS - 351 is equivalent to HD - 1 isolated in 1967 from diseased black larvae of the pink bollworm in Brownsville, Texas, USA (ATCC SD - 1275; e.g., DF), Bacillus thuringiensis subsp. kurstaki SB4 was isolated from the cadavers of larvae of the African sugarcane borer (E. saccharina) (NRRL B - 50753; e.g., ) from Beta of BASF Agricultural Specialities (Pty) Ltd., South Africa, 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 585215B1; e.g., ) from Valent BioSciences, Switzerland, Beauveria bassiana GHA (ATCC 74250; e.g., 22WGP) from Laverlam Int.Corp., USA, Beauveria bassiana JW - 1 (ATCC74040; e.g., ) from CBC(Europe) S.r.l., Italy, Beauveria bassiana PPRI 5339 was isolated from the larvae of the tortoise beetle Conchyloctenia punctata (NRRL 50757; e.g., ),The Bradyrhizobium elkanii strain SEMIA 5019 (also known as 29W) was isolated in Rio de Janeiro, Brazil and SEMIA 587 was isolated in 1967 in the State of Rio Grande do Sul, from an area previously inoculated with North American isolates and has been used for commercial inoculants since 1968 (Appl. Environ. Microbiol. [Applied and Environmental Microbiology] 73(8), 2635, 2007; e.g., GELFIX 5 from BASF Agricultural Specialties Ltd., Brazil), Bradyrhizobium japonicum 532c was isolated from a field in Wisconsin, USA (Nitragin 61A152; Can. J. Plant Sci. [Canadian Journal of Plant Sciences] 70, 661 - 666, 1990; e.g., (Super), Bradyrhizobium japonicum E-109 variant of strain USDA 138 (INTA E109, SEMIA 5085; Eur. J. Soil Biol. [European Journal of Soil Biology] 45, 28 - 35, 2009; Biol. Fertil. Soils [Biology and Fertility of Soils] 47, 81–89, 2011); Bradyrhizobium japonicum strains known to be deposited at SEMIA by Appl. Environ. Microbiol. [Applied and Environmental Microbiology] 73(8), 2635, 2007: Bradyrhizobium japonicum SEMIA 5079 was isolated from soil by Embrapa - Cerrados in the Cerrados region of Brazil and has been used for commercial inoculants since 1992 (CPAC 15; e.g., GELFIX 5 or ADHERE60 from BASF Agricultural Specialties Ltd., Brazil), Bradyrhizobium japonicum SEMIA 5080 was obtained under laboratory conditions by Embrapa - Cerrados in Brazil and has been used for commercial inoculants since 1992 and is a natural variant of SEMIA 586 (CB1809) originally isolated in the United States (CPAC7; e.g., GELFIX 5 or ADHERE 60 from BASF Agricultural Specialties Ltd., Brazil); Burkholderia species A396 was isolated from soil in Nikko, Japan in 2008 (NRRLB - 50319; WO 2013 / 032693; Marrone Bio Innovations, Inc., USA), Coniothyrium minitans CON / M / 91 - 08 was isolated from Brassica napus (WO 1996 / 021358; DSM 9660; e.g., WG, WG), harpin (α - β) protein (Science [Science] 257, 85 - 88, 1992; e.g., Messenger from Plant Health Care plc, UK TM or HARP - N - Tek), Helicoverpa armigera nucleopolyhedrovirus (HearNPV) (J. Invertebrate Pathol [Journal of Invertebrate Pathology]. 107, 112 - 126, 2011; e.g., from Koppert, 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 Basella alba 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 BiologicalsBioAg 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 Bacillus 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., South Africa), and the 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 TM PN) of Penicillium bilaiae (also known as P. bililaii) strains ATCC 18309 (= ATCC 74319), ATCC 20851 and / or ATCC 22348 (= ATCC 74318) were initially isolated from soil in Alberta, Canada (Fertilizer Res. 39, 97-103, 1994; Can. J. Plant Sci. 78(1), 91-102, 1998; US 5,026,417, WO 1995 / 017806; for example, Jump from Novozymes Biologicals BioAg Group, Canada ) Extracts of Reynoutria japonica Houtt. (EP 0307510 B1; for example, SC from Marrone BioInnovations, Davis, CA, USA or ) from BioFa AG, Germany ) Steinernema carpocapsae (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 ).

[0449] According to another embodiment of the mixture, at least one pesticidal agent II is selected from groups L1) to L5):

[0450] L1) Microbial pest control agents with fungicidal, bactericidal, virucidal and / or plant defense activator activity: Aureobasidium pullulans DSM 14940 and DSM 14941 (L1.1), Bacillus amyloliquefaciens AP-188 (L.1.2), 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 pseudokoningii JM41R (L.1.23), Trichoderma harzianum T-22 (L.1.24);

[0451] L2) Biochemical pest control agents with fungicidal, bactericidal, virucidal and / or plant defense activator activity: harpins (L.2.1), Reynoutria maxima extract (L.2.2);

[0452] L3) Microbial pesticidal 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);

[0453] L4) Biochemical pesticidal 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);

[0454] L5) Microbial pesticidal 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).

[0455] Furthermore, the present invention relates to agrochemical compositions which comprise a mixture of the following: at least one compound I (component 1) and at least one biopesticide selected from group L) (component 2), in particular at least one biopesticide selected from groups L1) and L2) as described above, and, if desired, at least one suitable adjuvant.

[0456] Furthermore, the present invention relates to agrochemical compositions which comprise a mixture of the following: at least one compound I (component 1) and at least one biopesticide selected from group L) (component 2), in particular at least one biopesticide selected from groups L3) and L4) as described above, and, if desired, at least one suitable adjuvant.

[0457] Also preferred are mixtures which comprise as pesticidal agent II (component 2) a biopesticide selected from groups L1), L3) and L5), preferably selected from those strains designated above as (L.1.2), (L.1.3), (L.1.4), (L.1.5), (L.1.6), (L.1.7), (L.1.8), (L.1.10), (L.1.11), (L.1.12), (L.1.13), (L.1.14), (L.1.15), (L.1.17), (L.1.18), (L.1.19), (L.1.20), L.1.21), (L.1.25), (L.1.26), (L.1.27), (L.3.1); (L.3.9), (L.3.16), (L.3.17), (L.5.1), (L.5.2), (L.5.3), (L.5.4), (L.5.5), (L.5.6), (L.5.7), (L.5.8); (L.4.2) and (L.4.1); even more preferably selected from (L.1.2), (L.1.6), (L.1.7), (L.1.8), (L.1.11), (L.1.12), (L.1.13), (L.1.14), (L.1.15), (L.1.18), (L.1.19), (L.1.20), (L.1.21), (L.3.1); (L.3.9), (L.3.16), (L.3.17), (L.5.1), (L.5.2), (L.5.5), (L.5.6); (L.4.2) and (L.4.1). These mixtures are particularly suitable for treating propagation material, i.e. for seed treatment purposes, and are equally suitable for soil treatment. These seed treatment mixtures are particularly suitable for crops such as cereals, maize and leguminous plants such as soybeans.

[0458] Also preferred are mixtures comprising a biopesticide as pesticidal agent II (component 2), which biopesticide is selected from group L1), L3) and L5), preferably selected from the strains 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 selected from (L1.2), (L1.7), (L1.11), (L1.13), (L1.14), (L1.15), (L1.18), (L1.23), (L3.3), (L3.4), (L3.6), (L3.7), (L3.8), (L3.10), (L3.11), (L3.12), (L3.15) and (L4.2). These mixtures are particularly suitable for the foliar treatment of cultivated plants, preferably vegetables, fruits, vines, cereals, maize and leguminous crops such as soybeans.

[0459] Compositions comprising mixtures of active ingredients can be prepared by customary means, for example by the means given for the compositions of compound I.

[0460] When live microorganisms such as pesticidal agents II from group L1), L3) and L5) form part of the composition, such compositions can be prepared by customary means (e.g. H.D. Burges: Formulation of Microbial Biopesticides, Springer, 1998; WO 2008 / 002371, US 6,955,912, US 5,422,107).

[0461] I. Synthesis examples

[0462] Example 1:trans-9-Fluoro-5-(8-fluoroquinolin-3-yl)-1,2,3-trimethyl-2,3-dihydro-1H-benzo[e][1,4]diazepine Preparation

[0463] Step 1: Preparation of (2,3-difluorophenyl)(8-fluoroquinolin-3-yl)methanol

[0464]

[0465] At 0 °C, under N2, to a solution of 1,2-difluoro-3-iodobenzene (4.1 g, 0.017 mol) in THF (40 mL) was added iPrMgCl (2 M) (8.59 mL, 0.0179 mol) and the mixture was stirred at 0 °C for 30 min. Then, at 0 °C, 8-fluoroquinoline-3-carbaldehyde (2.5 g, 0.014 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. The residue was purified by column (PE:EtOAc = 9:1) and concentrated to give (2,3-difluorophenyl)(8-fluoroquinolin-3-yl)methanol (3.4 g, 82%) as a white solid.

[0466] 1 1H NMR (400 MHz, CDCl3) δ [ppm] = 8.98 (s, 1H) 8.22 (s, 1H) 7.62 (d, J = 8.13 Hz, 1H) 7.50 (td, J = 7.91, 4.94 Hz, 1H) 7.37 - 7.44 (m, 1H) 7.31 - 7.37 (m, 1H) 7.07 - 7.21 (m, 2H) 6.42 (s, 1H).

[0467] Step 2: Preparation of (2,3-difluorophenyl)(8-fluoroquinolin-3-yl)methanone

[0468]

[0469] To a solution of (2,3-difluorophenyl)(8-fluoroquinolin-3-yl)methanol (3.4 g, 0.011 mol) in THF (40 mL) was added MnO2 (19 g, 0.117 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 to give (2,3-difluorophenyl)(8-fluoroquinolin-3-yl)methanone as a white solid (2.7 g, 79.9%). The title compound was used directly without further purification.

[0470] 1 1H NMR (400 MHz, CDCl3) δ [ppm] = 9.38 (s, 1H) 8.59 (d, J = 1.63 Hz, 1H) 7.71 - 7.79 (m, 1H) 7.55 - 7.66 (m, 2H) 7.42 - 7.51 (m, 2H) 7.28 - 7.36 (m, 1H).

[0471] Step 3: Preparation of 9-fluoro-5-(8-fluoroquinolin-3-yl)-2,3-dimethyl-2,3-dihydro-1H-benzo[e][1,4]diazepine Preparation

[0472]

[0473] To a solution of butane-2,3-diamine dihydrochloride (0.41 g, 0.0026 mol) in nBuOH (20 mL) was added Na2CO3 (0.99 g, 0.009 mol) and (2,3-difluorophenyl)(8-fluoroquinolin-3-yl)methanone (0.75 g, 0.0026 mol), and the mixture was stirred at 120 °C under N2 for 16 h. TLC (PE:EtOAc = 3:1) showed completion of the reaction. The reaction mixture was filtered and the filtrate was concentrated. The residue was purified by column (PE:EtOAc = 9:1) and preparative HPLC (NH4HCO3) to give cis-9-fluoro-5-(8-fluoroquinolin-3-yl)-2,3-dimethyl-2,3-dihydro-1H-benzo[e][1,4]diazepine as a yellow solid (0.2 g, 21.6%) and trans-9-fluoro-5-(8-fluoroquinolin-3-yl)-2,3-dimethyl-2,3-dihydro-1H-benzo[e][1,4]diazepine as a yellow solid (0.2 g, 21.6%). (0.2 g, 21.6%) and trans-9-fluoro-5-(8-fluoroquinolin-3-yl)-2,3-dimethyl-2,3-dihydro-1H-benzo[e][1,4]diazepine (0.2 g, 21.6%).

[0474] cis-9-fluoro-5-(8-fluoroquinolin-3-yl)-2,3-dimethyl-2,3-dihydro-1H-benzo[e][1,4]diazepine

[0475] 1 1H NMR (400 MHz, MeOD) δ [ppm] = 8.99 (d, J = 2.00 Hz, 1H) 8.41 (t, J = 1.63 Hz, 1H) 7.82 (d, J = 8.00 Hz, 1H) 7.53 - 7.67 (m, 2H) 7.16 (ddd, J = 11.57, 7.88, 1.31 Hz, 1H) 6.77 (d, J = 8.13 Hz, 1H) 6.62 (td, J = 7.97, 4.94 Hz, 1H) 4.05 - 4.11 (m, 1H) 3.91 (qd, J = 6.73, 1.81 Hz, 1H) 1.51 (d, J = 6.75 Hz, 3H) 1.21 (d, J = 6.50 Hz, 3H)

[0476] trans-9-Fluoro-5-(8-fluoroquinolin-3-yl)-2,3-dimethyl-2,3-dihydro-1H-benzo[e][1,4]diazepine

[0477] 1 1H NMR (400 MHz, MeOD) δ [ppm] = 9.02 (d, J = 2.00 Hz, 1H) 8.38 (t, J = 1.75 Hz, 1H) 7.80 (d, J = 8.13 Hz, 1H) 7.56 - 7.66 (m, 2H) 7.20 (ddd, J = 11.13, 7.88, 1.50 Hz, 1H) 6.81 - 6.86 (m, 1H) 6.73 - 6.79 (m, 1H) 3.85 - 3.92 (m, 1H) 3.62 (dd, J = 8.07, 6.57 Hz, 1H) 1.48 (d, J = 6.50 Hz, 3H) 1.30 (d, J = 6.38 Hz, 3H).

[0478] Preparation of butane-2,3-diamine dihydrochloride

[0479]

[0480] Under N2, Ni - Al alloy (25 g, 0.276 mol) was added to a solution of butane - 2,3 - dione dioxime (4 g, 0.034 mol) in THF (90 mL), and the mixture was heated to 60 °C for 30 min. Then, an aqueous NaOH solution (3.5 M) (87 mL, 0.306 mol) was slowly added under N2, and the mixture was stirred at 60 °C for 16 h. The reaction mixture was filtered and the filtrate was distilled at 150 °C under atmospheric pressure to obtain an aqueous solution of butane - 2,3 - diamine dihydrochloride. Then, this aqueous solution was adjusted to pH = 2 with an aqueous HCl solution (3 M), stirred for 0.5 h and concentrated to give butane - 2,3 - diamine dihydrochloride as the HCl salt as a white solid (3.4 g, 62%).

[0481] 1 1H NMR (400 MHz, D2O) δ [ppm] = 3.50 - 3.75 (m, 2H) 1.23 - 1.44 (m, 6H).

[0482] Step 4: Preparation of trans - 9 - fluoro - 5 - (8 - fluoroquinolin - 3 - yl) - 1,2,3 - trimethyl - 2,3 - dihydro - 1H - benzo[e][1,4]diazepine Preparation

[0483]

[0484] At 0 °C, under N2, NaH (60%) (0.040 g, 1.08 mmol) was added to a solution of trans - 9 - fluoro - 5 - (8 - fluoroquinolin - 3 - yl) - 2,3 - dimethyl - 2,3 - dihydro - 1H - benzo[e][1,4]diazepine (0.17 g, 0.50 mmol) in DMF (2 mL), and the mixture was stirred at 0 °C under N2 for 0.5 h. Then, MeI (0.107 g, 0.756 mmol) in DMF (0.5 mL) was added at 0 °C and the mixture was stirred at 20 °C for 16 h. TLC (PE:EtOAc = 1:1) showed the reaction was complete. The reaction mixture was quenched with H2O (5 mL) and extracted with EtOAc (10 mL×3). The organic layer was washed with brine (20 mL), dried over Na2SO4 and concentrated. The residue was purified by column (PE:EtOAc = 9:1) and preparative HPLC (NH4HCO3) to give trans - 9 - fluoro - 5 - (8 - fluoroquinolin - 3 - yl) - 1,2,3 - trimethyl - 2,3 - dihydro - 1H - benzo[e][1,4]diazepine (0.1 g, 56%).

[0485] 11H NMR (400 MHz, CDCl3) δ [ppm] = 9.23 (d, J = 1.75 Hz, 1H) 8.30 (s, 1H) 7.63 (d, J = 8.00 Hz, 1H) 7.38 - 7.56 (m, 2H) 7.12 - 7.21 (m, 1H) 7.05 (td, J = 7.85, 4.69 Hz, 1H) 6.83 (d, J = 7.50 Hz, 1H) 3.55 - 3.70 (m, 1H) 3.15 - 3.27 (m, 1H) 2.97 (d, J = 5.00 Hz, 3H) 1.51 (d, J = 6.25 Hz, 3H) 1.19 (d, J = 6.13 Hz, 3H).

[0486] Table I: Compounds Ex-10 to Ex-14 having formula I, where R 5 , R 6 , R 7 , R 8 , R 9 , X and Zm have the meanings defined in each row.

[0487] *HPLC: High Performance Liquid Chromatography; HPLC-column Kinetex XB C18 1,7 μ (50×2,1 mm); Eluent: Acetonitrile / Water + 0.1% Trifluoroacetic Acid (Gradient from 5:95 to 100:0 in 1.5 min at 60 °C, Flow Gradient from 0.8 to 1.0 ml / min in 1.5 min);

[0488] *LCMS: Liquid Chromatography-Mass Spectrometry; Shimadzu Nexera LC-30LCMS-2020 (ESI+), using HPLC-column Kinetex XB C18 1,7 μ (50×2,1 mm); Eluent: Acetonitrile / Water + 0.1% Trifluoroacetic Acid (Gradient from 5:95 to 100:0 in 1.5 min at 60 °C, Flow Gradient from 0.8 to 1.0 ml / min in 1.5 min);

[0489] R t : Retention time in minutes.

[0490]

[0491] #imgpt129#

[0492] II. Biological example

[0493] Greenhouse

[0494] 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.

[0495] This stock solution is then diluted with the solvent-emulsifier-water mixture to the final concentrations given in the table below.

[0496] Example 1 - Preventive fungicidal control of Botrytis cinerea on green pepper leaves

[0497] Green pepper seedlings are grown in pots to the 4- to 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 Botrytis cinerea spore suspension. The plants are then immediately transferred to a humid chamber. After 5 days at 22°C to 24°C and saturated relative humidity, the degree of fungal infestation on the leaves is visually evaluated as % diseased leaf area.

[0498] In this test, samples treated with 250 ppm of the active substances from Examples Ex-10 and Ex-11 respectively showed a pathogen growth rate of up to 8%, while 90% of the untreated plants were infected.

[0499] In this test, samples treated with 125 ppm of the active substances from Examples Ex-15, Ex-16, and Ex-17 respectively showed a pathogen growth rate of up to 7%, while 90% of the untreated plants were infected.

[0500] Example 2 - Long-term control of Botrytis cinerea on green pepper leaves

[0501] Green pepper seedlings are grown in pots to the 4- to 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. Then, the plants are 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 are then immediately transferred to a humid chamber. After 5 days at 22°C to 24°C and saturated relative humidity, the degree of fungal infestation on the leaves is visually evaluated as % diseased leaf area.

[0502] In this test, the sample treated with 125 ppm of the active substance from Example Ex-17 showed a pathogen growth rate of up to 15%, while 90% of the untreated plants were infected.

[0503] Example 3 - Preventive fungicidal control of white mold on soybeans caused by Sclerotinia sclerotiorum

[0504] Soybean seedlings were planted in pots. These plants were sprayed with the aforementioned spray solution to runoff, which contained the active ingredient or mixture at the concentrations mentioned in the following table. The next day, the treated plants were inoculated with a 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.

[0505] In this test, samples treated with 125 ppm of the active substances from Examples Ex-15, Ex-16, and Ex-17 respectively showed a pathogen growth rate of up to 11%, while 90% of the untreated plants were infected.

[0506] Example 4 - Preventive fungicidal control of white mold on cabbage caused by Sclerotinia sclerotiorum

[0507] Cabbages were grown in pots to the 13 - 14 leaf stage. These plants were sprayed with the aforementioned spray solution to runoff, 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, cabbage leaves were inoculated with a 50 μl mixture of ground petals, methylcellulose, 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.

[0508] In this test, samples treated with 125 ppm of the active substance from Example Ex-17 showed a pathogen growth rate of up to 8%, while 80% of the untreated plants were infected.

[0509] Microtest

[0510] The active compound was formulated individually as a stock solution at a concentration of 10,000 ppm in dimethyl sulfoxide.

[0511] Example 5 - Activity against Botrytis cinerea in microtiter plate tests

[0512] The stock solutions were mixed in ratios, pipetted onto microtiter plates (MTPs) and diluted with water to the specified concentrations. Then, a spore suspension of Botrytis cinerea in an aqueous solution of biomalts or a yeast - bacteria - peptone - sodium acetate solution was added. The plates were placed in a water vapor - saturated chamber at a temperature of 18 °C. The MTPs were measured at 405 nm using an absorption photometer 7 days after inoculation.

[0513] In this test, samples treated with 31 ppm of the active substances from Examples Ex-10, Ex-12, Ex-15, Ex-16 and Ex-17 respectively showed a pathogen growth rate of 4%.

[0514] Example 6 - Activity against Corynespora zeae in microtiter plate tests

[0515] The active compounds were individually formulated as stock solutions at a concentration of 10,000 ppm in dimethyl sulfoxide. The stock solutions were mixed in ratios, pipetted onto microtiter plates (MTPs) and diluted with water to the specified concentrations. Then, spore suspensions of Corynespora zeae in aqueous biomalting solution or yeast - bacteriological peptone - sodium acetate solution were added.

[0516] In this test, samples treated with 31 ppm of the active substance from Example Ex-10 showed a pathogen growth rate of 8%.

[0517] Example 7 - Activity against Fusarium culmorum in microtiter plate tests

[0518] The stock solutions were mixed in ratios, pipetted onto microtiter plates (MTPs) and diluted with water to the specified concentrations. Then, spore suspensions of Fusarium culmorum in aqueous biomalting solution or yeast - bacteriological peptone - glycerol or DOB solution were added.

[0519] In this test, samples treated with 31 ppm of the active substances from Examples Ex-9, Ex-10, Ex-15, Ex-16 and Ex-17 respectively showed a pathogen growth rate of up to 2%.

[0520] Example 8 - Activity against Alternaria solani - induced leaf spot on wheat in microtiter plate tests

[0521] The active compounds were individually formulated as stock solutions at a concentration of 10,000 ppm in dimethyl sulfoxide. The stock solutions were mixed in ratios, pipetted onto microtiter plates (MTPs) and diluted with water to the specified concentrations. Then, spore suspensions of Alternaria solani in aqueous biomalting solution or yeast - bacteriological peptone - glycerol or DOB solution were added.

[0522] In this test, samples treated with 31 ppm of the active substances from Examples Ex-15, Ex-16, Ex-17 showed a pathogen growth rate of up to 24%.

[0523] Example 9 - Activity against Cercospora sojina in microtiter plate tests

[0524] 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 in a ratio, pipetted onto a microtiter plate (MTP), and diluted with water to the specified concentration. Then, a spore suspension of Cercospora sojina in a biological malt aqueous solution or a yeast - bacterium peptone - sodium acetate solution was added.

[0525] In this test, samples treated with 31 ppm of the active substances from Examples Ex - 16 and Ex - 17 respectively showed a pathogen growth rate of 6%.

[0526] Example 10 - Activity against Corynespora cassiicola G413A mutant in microtiter plate test

[0527] 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 in a ratio, pipetted onto a microtiter plate (MTP), and diluted with water to the specified concentration. Then, a spore suspension of Corynespora cassiicola G413A mutant isolate in a biological malt aqueous solution or a yeast - bacterium peptone - sodium acetate solution was added.

[0528] In this test, samples treated with 31 ppm of the active substances from Examples Ex - 15, Ex - 16, and Ex - 17 respectively showed a pathogen growth rate of 11%.

[0529] Example 11 - Activity against leaf spot on wheat caused by Pyricularia oryzae in microtiter plate test

[0530] 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 in a ratio, 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 a yeast - bacterium peptone - glycerol or DOB solution was added.

[0531] In this test, samples treated with 31 ppm of the active substances from Examples Ex - 15 and Ex - 16 respectively showed a pathogen growth rate of up to 5%.

[0532] Example 12 - Activity against leaf spot on wheat caused by Septoria tritici in microtiter plate test

[0533] 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 in a ratio, 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 a yeast - bacterium peptone - glycerol or DOB solution was added.

[0534] In this test, samples treated with 31 ppm of the active substances from Examples Ex-15, Ex-16, and Ex-17, respectively, showed pathogen growth rates of up to 21%.

[0535] The measured parameters were compared to the growth rate of the control variant without the active compound (100%) and the fungus-free blank value to determine the relative growth rate of the pathogen in the respective active compound (in %).

Claims

1. A compound of formula I Y is N, CR 1 ; R 1 independently selected from H, halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl in each case; R 4 independently selected from H, halogen, CN, C1-C4-alkyl, C1-C4-haloalkyl in each case; R 5 is hydrogen, halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl or benzyl, a heteroaromatic group and a CH2-heteroaromatic group, where the last-mentioned 10 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; R 6 is hydrogen, halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl or benzyl, a heteroaromatic group and a CH2-heteroaromatic group, where the last-mentioned 10 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; 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 is hydrogen, halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl or benzyl, a heteroaromatic group and a CH2-heteroaromatic group, where the last-mentioned 10 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 is hydrogen, halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl or benzyl, a heteroaromatic group and a CH2-heteroaromatic group, where the last-mentioned 10 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 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 heterocyclic ring containing 1, 2 or 3 heteroatoms selected from O and S as ring members; R 9 is CN, CH2CN, CH(CH3)CN, CH(=O), -C(=O)C1-C6-alkyl, -C(=O)C2-C6 alkenyl, -C(=O)C2-C6 alkynyl, -C(=O)C3-C6 cycloalkyl, -C(=O)-N(H)C1-C4 alkyl, -C(=O)-N(C1-C4 alkyl)2, C1-C6 alkyl, C1-C6 alkoxy, C1-C4 haloalkyl, C3-C6 cycloalkyl, C3-C6 halocycloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, -S(=O)2-R 9a , a five- or six-membered heteroaryl, aryl or benzyl; wherein the heteroaryl contains 1, 2 or 3 heteroatoms selected from N, O and S as ring members; wherein the benzene rings in the aryl and benzyl are unsubstituted or carry 1, 2, 3, 4 or 5 substituents selected from the group consisting of: CN, halogen, OH, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy and C1-C4 haloalkoxy; wherein the benzene ring in the benzyl is unsubstituted or carries 1, 2 or 3 substituents selected from the group consisting of: CN and halogen; 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 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; X is independently 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; Z is independently 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; m is 0, 1, 2 or 3; or its N-oxide, tautomer, stereoisomer or agriculturally acceptable salt, provided that If Y is CR 1 , then R 5 , R 6 , R 7 , R 8 cannot all be H; If Y is CR 1 , and R 5 , R 6 is CH3, and R 7 , R 8 is H, then R 9 cannot be CH3; and If Y is CR 1 , and if R 5 、R 6 is H, and R 7 、R 8 is CH3, then R 9 cannot be CH3, allyl, or benzyl.

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 4 is H.

4. The compound according to any one of claims 1 to 3, wherein, R 5 and R 6 is H or a C1-C6-alkyl group.

5. The compound according to any one of claims 1 to 4, wherein R 5 and R 6 together with the C atom to which they are bonded form a C3-C6-cycloalkyl or (=O) group.

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

7. The compound according to any one of claims 1 to 6, wherein R 9 Selected from CH(=O), -C(=O)C1-C6-alkyl, -C1-C6-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C3-C6-halocycloalkyl.

8. The compound according to any one of claims 1 to 7, wherein X is selected from halogen, C1-C6-alkyl, O-C1-C6-alkyl, O-C1-C6-haloalkyl.

9. The compound according to any one of claims 1 to 8, wherein, Z is selected from halogen, C1-C6-alkyl, O-C1-C6-alkyl, O-C1-C6-haloalkyl.

10. A composition comprising a compound of formula I as defined in any one of claims 1 to 9, its N-oxide or an agriculturally acceptable salt thereof.

11. 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 9, or with a composition as defined in any one of claims 10.

12. A seed coated with from 0.1 to 10 kg / 100 kg of seed of at least one compound of formula I as defined in any one of claims 1 to 9 or an agriculturally acceptable salt thereof, or a composition as defined in any one of claims 10.

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