Novel substituted benzoxazine pyridinecarbonitrile compounds for combating phytopathogenic fungi

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.

Description

[0001] This invention relates to novel substituted benzoxazine pyridine carboxynitrile compounds as fungicides, their N-oxides and salts, and their uses. The invention also relates to compositions comprising at least one compound I, methods for combating plant pathogenic fungi, and seeds coated with at least one compound of formula I.

[0002] WO 2010125782, WO 2009119089, and JP 2011148714 disclose several benzoxazine pyridine carboxynitrile compounds. Furthermore, WO 2022243107 discloses several related substituted benzoxazine pyridine compounds. However, in many cases, especially at low application rates, the fungicidal activity of known compounds is unsatisfactory. Therefore, one object of the present invention is to provide compounds with improved activity and / or a broader activity spectrum against plant pathogenic fungi. Another object of the present invention is to provide fungicides with improved toxicological properties or improved environmental fate properties.

[0003] These and other purposes are achieved by pyridine compounds having formula (I) as defined below, and their agriculturally suitable salts.

[0004] Therefore, the present invention relates to compounds having formula I as fungicides, their N-oxides, and agriculturally acceptable salts.

[0005]

[0006] in

[0007] R 1 Selected from C1-C6-alkyl, O-C1-C6-alkyl, S-C1-C6-alkyl, halogen, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-ynyl, C2-C6-haloynyl, C3-C6-cycloalkyl;

[0008] R 2 Selected from H, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-ynyl, C2-C6-haloynyl, phenyl, benzyl, heterocyclic aromatic moiety and CH2-heterocyclic aromatic moiety.

[0009] These portions are either unsubstituted or composed of one to three groups R, independently selected from the following groups. 2a replace:

[0010] Halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, O-C1-C6-alkyl;

[0011] R3 Selected from H, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-ynyl, C2-C6-haloynyl, phenyl, benzyl, heterocyclic aromatic moiety and CH2-heterocyclic aromatic moiety.

[0012] These portions are either unsubstituted or composed of one to three groups R, independently selected from the following groups. 3a replace:

[0013] Halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, O-C1-C6-alkyl;

[0014] or

[0015] R 2 and R 3 Together with the C atoms they are bonded to, they form C=O;

[0016] or

[0017] R 2 and R 3 Together with the C atoms they are bonded to, they form 3-, 4-, 5-, or 6-membered saturated carbon rings, or 3-, 4-, 5-, or 6-membered saturated heterocycles containing 1, 2, or 3 heteroatoms selected from O, N, and S as ring members.

[0018] These portions are either unsubstituted or substituents R selected independently from the following groups: 23 Substitution: Halogen, C1-C6-alkyl or C1-C6-haloalkyl;

[0019] X 1 Selected from H, halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, O-C1-C6-alkyl, S-C1-C6-alkyl, O-C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, phenyl, benzyl, O-phenyl, O-benzyl, S-phenyl, S-benzyl.

[0020] These cyclic moieties are either unsubstituted or composed of one to three groups R, independently selected from the following groups: X1 replace:

[0021] Halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, O-C1-C6-alkyl;

[0022] X 2Selected from H, halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, O-C1-C6-alkyl, S-C1-C6-alkyl, O-C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, phenyl, benzyl, O-phenyl, O-benzyl, S-phenyl, S-benzyl;

[0023] These cyclic moieties are either unsubstituted or composed of one to three groups R, independently selected from the following groups: X2 replace:

[0024] Halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, O-C1-C6-alkyl.

[0025] N-oxides can be prepared from the compounds of the present invention by conventional oxidation methods, for example by treating compound I with an organic peracid such as m-chloroperoxybenzoic acid (see WO 03 / 64572 or J. Med. Chem. 38(11), 1892-903, 1995); or with an inorganic oxidizing agent such as hydrogen peroxide (see J. Heterocyc. Chem. 18(7), 1305-8, 1981) or a potassium persulfate preparation (see J. Am. Chem. Soc. 123(25), 5962-5973, 2001). Oxidation can produce pure mono-N-oxides or mixtures of different N-oxides, which can be separated by conventional methods such as chromatography.

[0026] Agriculturally acceptable salts of compounds of formula I particularly encompass salts of cations or acid addition salts of acids, where the cations and anions do not adversely affect the fungicidal activity of compound I. Therefore, suitable cations include, in particular, alkali metal (preferably sodium and potassium) ions, alkaline earth metal (preferably calcium, magnesium, and barium) ions, transition metal (preferably manganese, copper, zinc, and iron) ions, and also ammonium ions, which, if desired, may be substituted with one to four C1-C4-alkyl substituents and / or one phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, in addition to phosphonium ions, sulfonium ions, preferably tri(C1-C4-alkyl)sulfonium, and sulfonium oxide ions, preferably tri(C1-C4-alkyl)sulfonium oxide.

[0027] Acceptable anions for acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and anions of C1-C4-alkyl acids, preferably formate, acetate, propionate, and butyrate. These can be formed by reacting compound I with an acid corresponding to the anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, or nitric acid.

[0028] Compounds having Formula I can exist as one or more stereoisomers. Various stereoisomers include enantiomers, diastereomers, blocked isomers resulting from restricted rotation around a single bond of an asymmetric group, and geometric isomers. They also form part of the subject matter of this 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 isolated from one or more other stereoisomers. Furthermore, those skilled in the art know how to isolate, enrich, and / or selectively prepare said stereoisomers. The compounds of this invention can exist as mixtures of stereoisomers (e.g., racemates), individual stereoisomers, or as optically active forms.

[0029] Compounds having formula I can exist in different crystal forms with varying biological activities. They also form part of the subject matter of this invention.

[0030] In terms of variables, the examples of intermediates obtained during the preparation of compound I correspond to the examples of compounds having formula I. The term "compound I" refers to a compound having formula I.

[0031] The intermediate compound is further described below. Those skilled in the art will readily understand that the preferred options for the substituents given herein in conjunction with Compound I, and especially the preferred options given for the corresponding substituents in the table below, apply accordingly to the intermediate. Therefore, the substituents in each case, independently of each other or more preferably in combination, have the meaning as defined herein.

[0032] If the synthesis produces a mixture of isomers, separation is not usually required, as individual isomers may interconvert during post-treatment for use or during application (e.g., under the influence of light, acid, or alkali). Such transformations can also occur post-use, for example in the treated plant in the case of phytotreatment, or in the harmful fungus to be controlled.

[0033] In the definitions of variables given above, the collective terminology that typically represents the substituents under discussion is used. The term "C" n -C m"Indicates the number of possible carbon atoms in the substituent or substituent moiety discussed in each case."

[0034] The term "halogen" refers to fluorine, chlorine, bromine, and iodine.

[0035] The term "C1-C6-alkyl" refers to a straight-chain or branched saturated hydrocarbon group having 1 to 6 carbon atoms, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, hexyl, 1-methyl 1,1-Dimethylbutyl, 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 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), and 1,1-dimethylethyl (tert-butyl).

[0036] The term "C1-C6-haloalkyl" refers to an alkyl group having one or six carbon atoms as defined above, wherein some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned 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.

[0037] The term "C1-C6-alkoxy" refers to a straight-chain or branched alkyl group having 1 to 6 carbon atoms bonded via oxygen at any position in the alkyl group. Examples are "C1-C4-alkoxy" groups, such as methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, or 1,1-dimethylethoxy.

[0038] The term "C1-C6-haloalkoxy" refers to C1-C6-alkoxy groups as defined above, where some or all of the hydrogen atoms in these groups can be replaced by halogen atoms as mentioned above. Examples are "C1-C4-haloalkoxy" groups, such as OCH2F, OCHF2, OCF3, OCH2Cl, OCHCl2, OCCl3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC2F5 2-Fluoropropoxy, 3-Fluoropropoxy, 2,2-Difluoropropoxy, 2,3-Difluoropropoxy, 2-Chloropropoxy, 3-Chloropropoxy, 2,3-Dichloropropoxy, 2-Bromopropoxy, 3-Bromopropoxy, 3,3,3-Trifluoropropoxy, 3,3,3-Trichloropropoxy, OCH2-C2F5, OCF2-C2F5, 1-Fluoromethyl-2-Fluoroethoxy, 1-Chloromethyl-2-Chloroethoxy, 1-Bromomethyl-2-Bromoethoxy, 4-Fluorobutoxy, 4-Chlorobutoxy, 4-Bromobutoxy, or nonafluorobutoxy.

[0039] The term "C2-C6-alkenyl" refers to a straight-chain or branched unsaturated hydrocarbon group having 2 to 6 carbon atoms and double bonds at any position. Examples are "C2-C4-alkenyl" groups, such as vinyl, 1-propenyl, 2-propenyl (allyl), 1-methylvinyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, and 2-methyl-2-propenyl.

[0040] The term “C2-C6-haloalkenyl” refers to an alkyl group having 2 or 6 carbon atoms as defined above, wherein some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above.

[0041] The term "C2-C6-enoxy" refers to a straight-chain or branched alkenyl group having 2 to 6 carbon atoms bonded via oxygen at any position within the alkenyl group. An example is the "C2-C4-enoxy" group.

[0042] The term "C2-C6-ynyl" refers to a straight-chain or branched unsaturated hydrocarbon group having 2 to 6 carbon atoms and containing at least one triple bond. Examples are "C2-C4-ynyl" groups, such as ethynyl, prop-1-ynyl, prop-2-ynyl (propynyl), but-1-ynyl, but-2-ynyl, but-3-ynyl, and 1-methyl-prop-2-ynyl.

[0043] The term “C2-C6-haloalkynyl” refers to an alkyl group having 2 or 6 carbon atoms as defined above, wherein some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as mentioned above.

[0044] The term "C2-C6-alkynyloxy" refers to a straight-chain or branched alkynyl group having 2 to 6 carbon atoms bonded via oxygen at any position in the alkynyl group. An example is the "C2-C4-alkynyloxy" group.

[0045] The term "C3-C6-cycloalkyl" refers to a monocyclic saturated hydrocarbon group having 3 to 6 carbon ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. Therefore, saturated ternary, quaternary, pentary, hexaternary, octary, nonaternary, or decacyclic carbon groups or carbon rings are "C3-C6". 10 -cycloalkyl.

[0046] The term "C3-C6-cycloalkenyl" refers to a partially unsaturated monocyclic 3-, 4-, 5-, or 6-membered carbon ring having 3 to 6 carbon ring members and at least one double bond, such as cyclopentenyl, cyclopentadienyl, and cyclohexadienyl. Therefore, partially unsaturated 3-, 4-, 5-, 6-, 7-, 8-, 9-, or 10-membered carbon rings or groups are "C3-C6-cycloalkenyl". 10 -cycloalkenyl".

[0047] The term “C3-C8-cycloalkyl-C1-C4-alkyl” refers to an alkyl group having 1 to 4 carbon atoms (as defined above), wherein one hydrogen atom of the alkyl group is replaced by a cycloalkyl group having 3 to 8 carbon atoms (as defined above).

[0048] The term "saturated or partially unsaturated ternary, quaternary, pentaneous, hexanal, octaneous, nonanal, or decacyclic heterocyclic groups or heterocycles, wherein the heterocyclic group or heterocycle contains 1, 2, 3, or 4 heteroatoms selected from N, O, and S" should be understood to refer to both saturated and partially unsaturated heterocycles, wherein the ring member atoms of the heterocycle, in addition to carbon atoms, include 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of O, N, and S. For example:

[0049] Three- or four-membered saturated heterocycles containing one or two heteroatoms selected from the group consisting of O, N, and S as ring members, such as ethylene oxide, aziridine, thiocyclopropane, oxetane, azirbutane, thiethane, [1,2]dioxetane, [1,2]dithiethane, and [1,2]diazabutane; and

[0050] Five- or six-membered saturated or partially unsaturated heterocycles containing one, two, or three heteroatoms selected from the group consisting of O, N, and S as ring members, such as 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothiophenyl, 3-tetrahydrothiophenyl, 2-pyrrolyl, 3-pyrrolyl, 3-isooxazolyl, 4-isooxazolyl, 5-isooxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 3-pyrrolyl, 4-pyrrolyl, 5-pyrrolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 2-imidazolyl, 4-imidazolyl, 1,2,4-oxadiazolyl-3-yl, 1,2,4-oxadiazolyl- 5-yl, 1,2,4-thiadiazolidine-3-yl, 1,2,4-thiadiazolidine-5-yl, 1,2,4-triazolidine-3-yl, 1,3,4-oxadiazolidine-2-yl, 1,3,4-thiadiazolidine-2-yl, 1,3,4-triazolidine-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-pyrrololin-2-yl, 2-pyrrololin-3-yl, 3-pyrrololin-2-yl, 3-pyrrololin-3-yl, 2-isooxazoline-3-yl 3-Isoxazoline-3-yl, 4-Isoxazoline-3-yl, 2-Isoxazoline-4-yl, 3-Isoxazoline-4-yl, 4-Isoxazoline-4-yl, 2-Isoxazoline-5-yl, 3-Isoxazoline-5-yl, 4-Isoxazoline-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-Dihydropyrazole-1-yl, 2,3-Dihydropyrazole-2-yl, 2,3-Dihydropyrazole-3-yl, 2,3-Dihydropyrazole-4-yl, 2,3- Dihydropyrazole-5-yl, 3,4-dihydropyrazole-1-yl, 3,4-dihydropyrazole-3-yl, 3,4-dihydropyrazole-4-yl, 3,4-dihydropyrazole-5-yl, 4,5-dihydropyrazole-1-yl, 4,5-dihydropyrazole-3-yl, 4,5-dihydropyrazole-4-yl, 4,5-dihydropyrazole-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, 2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-Dihydrooxazol-4-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1,3-dioxane-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothiophenyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperidinyl, 1,3,5-hexahydrotriazin-2-yl and 1,2,4-hexahydrotriazin-3-yl, and corresponding -subunit groups; and,

[0051] Seven-membered saturated or partially unsaturated heterocycles such as tetra- and hexahydroazapyridines, such as 2,3,4,5-tetrahydro[1H]azapyr-1-, -2-, -3-, -4-, -5-, -6- or -7-yl, 3,4,5,6-tetrahydro[2H]azapyr-2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,4,7-tetrahydroazapyridines. [1H]aza-1-, -2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,6,7-tetrahydro[1H]aza-1-, -2-, -3-, -4-, -5-, -6- or -7-yl, hexahydroaza-1-, -2-, -3- or -4-yl, tetra- and hexahydroxyaza-yl such as 2,3,4,5- Tetrahydro[1H]oxazine-2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,4,7-tetrahydro[1H]oxazine-2-, -3-, -4-, -5-, -6- or -7-yl, 2,3,6,7-tetrahydro[1H]oxazine-2-, -3-, -4-, -5-, -6- or -7-yl, hexahydroaza The following groups are used: -1-, -2-, -3- or -4-yl groups, tetra- and hexahydro-1,3-diazazyl groups, tetra- and hexahydro-1,4-diazazyl groups, tetra- and hexahydro-1,3-oxazyl groups, tetra- and hexahydro-1,4-oxazyl groups, tetra- and hexahydro-1,3-dioxazyl groups, tetra- and hexahydro-1,4-dioxazyl groups and their corresponding - subunit groups.

[0052] The term “substituted” refers to being replaced by one, two, three, or up to the maximum possible number of substituents.

[0053] The terms "5- or 6-membered heteroaryl" or "5- or 6-membered heteroaromatic" refer to aromatic ring systems that, in addition to a carbon atom, contain 1, 2, 3, or 4 heteroatoms independently selected from the group consisting of N, O, and S.

[0054] Five-membered heteroaryl groups, such as pyrrolo-1-yl, pyrrolo-2-yl, pyrrolo-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, imidazole-1-yl, imidazole-2-yl, imidazole-4-yl, imidazole-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

[0055] Six-membered heteroaryl groups, 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.

[0056] Specific embodiments of the compounds of the present invention are described below. The specific meanings of the corresponding substituents are further detailed therein, wherein these meanings, in each case individually and in arbitrary combinations thereof, constitute specific embodiments of the present invention.

[0057] Furthermore, in terms of variables, the examples of compound I are generally applicable to intermediates as well.

[0058] According to one embodiment of a compound having formula I, R 1 Selected from C1-C6-alkyl, S-C1-C6-alkyl, O-C1-C6-alkyl, halogen, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-ynyl, C2-C6-haloynyl, and C3-C6-cycloalkyl. According to another embodiment of Formula I, R... 1 It is a halogen, especially F, Cl, Br or l, more specifically F, Cl or Br, especially F or Cl.

[0059] According to another embodiment of formula I, R 1 It is F.

[0060] According to another embodiment of formula I, R 1 It is Cl.

[0061] According to another embodiment of formula I, R 1 It is Br.

[0062] According to another embodiment of formula I, R 1 It is a C1-C6-alkyl, especially a C1-C4-alkyl, such as CH3 or C2H5, especially CH3 or CH2CH3.

[0063] According to another embodiment of formula I, R 1 It is a C1-C6-haloalkyl, especially a C1-C4-haloalkyl, such as CF3.

[0064] According to another embodiment of formula I, R 1 It is C2-C6-alkenyl, especially C2-C4-alkenyl, such as CH=CH2, C(CH3)=CH2, CH2CH=CH2.

[0065] According to another specific embodiment of Formula I, R 1 It is an O-C1-C6-alkyl, particularly a C1-C4-alkyl, and more specifically a C1-C2-alkoxy. R 1 It is such as OCH3 or OCH2CH3.

[0066] According to another specific embodiment of Formula I, R 1 It is S-C1-C6-alkyl, particularly C1-C4-alkyl, and more specifically C1-C2-alkoxy. R 1 It is such as SCH3 or SCH2CH3.

[0067] According to another specific embodiment of Formula I, R 1 It is cyclopropyl, cyclobutyl, or cyclopentyl.

[0068] According to the R of the present invention 1 Particularly preferred embodiments are shown in Table P2 below, where each row from P1-1 to P1-16 corresponds to a specific embodiment of the invention, and further, any combination of P1-1 to P1-16 constitutes a preferred embodiment of the invention. (With R) 1 The connection points of bonded carbon atoms are marked with "#" in the diagram.

[0069] Table P1:

[0070]

[0071] According to one embodiment of a compound having formula I, R 2 In each case, the groups are independently selected from H, F, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, phenyl, and benzyl.

[0072] These portions are either unsubstituted or composed of one to three groups R, independently selected from the following groups. 2a replace:

[0073] Halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, O-C1-C6-alkyl.

[0074] According to one embodiment of a compound having formula I, R 2 In each case, the alkyl group is independently selected from C1-C6-alkyl (Example 2.1), C1-C6-haloalkyl (Example 2.2), H (Example 2.3), phenyl, CH2-phenyl (Example 2.4), wherein the phenyl and CH2-phenyl groups are unsubstituted or substituted with one or two halogens.

[0075] According to another embodiment of a compound having formula I, R 2 It is H, CH3, or CF3.

[0076] According to another embodiment of a compound having formula I, R 2 It is CH3.

[0077] According to another embodiment of a compound having formula I, R 2 It's H.

[0078] According to another embodiment of a compound having formula I, R 2 It is H, CH2CH3, CH(CH3)2, CH(CH3)CH2CH3, C(CH3)3, CH2-CH(CH3)2, CH2-C(CH3)3.

[0079] According to another embodiment of a compound having formula I, R 2 It 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.

[0080] According to one embodiment of a compound having formula I, R 3 In each case, the groups are independently selected from H, F, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, phenyl, and benzyl.

[0081] These portions are either unsubstituted or composed of one to three groups R, independently selected from the following groups. 3a replace:

[0082] Halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, O-C1-C6-alkyl.

[0083] According to one embodiment of a compound having formula I, R 3 In each case, the components were independently selected from C1-C6-alkyl (Example 3.1) and H (Example 3.2).

[0084] According to another embodiment of a compound having formula I, R 3 It is H, CH3, 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.

[0085] According to another embodiment of a compound having formula I, R 3 It is H or CH3.

[0086] According to another embodiment of a compound having formula I, R 3 It's H.

[0087] According to another embodiment of a compound having formula I, R 3 It is CH3.

[0088] According to another embodiment of a compound having formula I, R 2 and R 3 Together with the C atoms they are bonded to, they form C=O or C3-C6-cycloalkyl, or 3- to 6-membered saturated heterocycles containing 1, 2 or 3 heteroatoms from the group consisting of O, N and S; wherein the cycloalkyl or heterocycle may be unsubstituted or substituted with halogens, C1-C6-alkyl, or C1-C6-haloalkyl.

[0089] According to another embodiment of a compound having formula I, R 2 and R 3 Formation = O (Example 3.3).

[0090] According to another embodiment of a compound having formula I, R 2 and R 3 C3-C6-cycloalkyl groups are formed (Example 3.4).

[0091] According to another embodiment of a compound having formula I, R 2 and R 3 Forming 3- to 6-membered saturated heterocycles containing 1, 2, or 3 heteroatoms from groups composed of O and S.

[0092] According to another embodiment of a compound having formula I, R 2 and R 3 Formation of 3- to 6-membered saturated heterocycles containing one O (Example 3.5).

[0093] According to the R of the present invention 2 R 3Preferred embodiments are shown in Table P2 below, where each row from P2-1 to P2-19 corresponds to a specific embodiment of the invention, and P2-1 to P2-19 can also be arbitrarily combined with each other to form preferred embodiments of the invention. (With R) 2 and R 3 The connection points of bonded carbon atoms are marked with "#" in the diagram.

[0094] Table P2:

[0095]

[0096]

[0097] According to one embodiment of a compound having Formula I, X 1 In each case, the individual elements were independently selected from H, halogen (Example X1.1), CN, C1-C6-alkyl (Example X1.2), C1-C6-haloalkyl (Example X1.3), O-C1-C6-alkyl (Example X1.4), and O-C1-C6-haloalkyl (Example X1.5).

[0098] According to one embodiment of a compound having Formula I, X 1 In each case, it is independently selected from H and halogens.

[0099] According to one embodiment of a compound having Formula I, X 1 It is halogen.

[0100] According to one embodiment of a compound having Formula I, X 2 In each case, the individual components were independently selected from H, halogen (Example X2.1), CN, C1-C6-alkyl (Example X2.2), C1-C6-haloalkyl (Example X2.3), O-C1-C6-alkyl (Example X2.4), and O-C1-C6-haloalkyl (Example X2.5).

[0101] According to one embodiment of a compound having Formula I, X 2 In each case, it is independently selected from H and halogens.

[0102] According to one embodiment of a compound having Formula I, X 2 It is halogen.

[0103] Compounds having Formula I contain one or more chiral centers and are typically obtained as a mixture of racemic and / or diastereomers. Stereoisomers can be separated and isolated in pure form using methods known to those skilled in the art, such as by using chiral HPLC.

[0104] Therefore, according to the present invention, a compound having a chiral center and possessing Formula I can be used in the following form:

[0105] A racemic mixture of (R)-enantiomers and (S)-enantiomers;

[0106] -A mixture of (R)-enantiomers and (S)-enantiomers in any other proportion;

[0107] -Pure (R) enantiomer; or

[0108] -Pure (S)-enantiomer.

[0109] According to one specific embodiment, a compound having Formula I is provided and used in an enantiomeric excess (ee) of at least 40%, such as at least 50%, 60%, 70% or 80%, preferably at least 90%, more preferably at least 95%, even more preferably at least 98%, and most preferably at least 99% in the (R)-enantiomer form.

[0110] According to one specific embodiment, a compound having Formula I is provided and used in an enantiomeric excess (ee) of at least 40%, such as at least 50%, 60%, 70% or 80%, preferably at least 90%, more preferably at least 95%, even more preferably at least 98%, and most preferably at least 99% in the (S)-enantiomer form.

[0111] Therefore, according to the present invention, compounds having two chiral centers and possessing formula I can be used in the following form:

[0112] -(R,R)-enantiomers and (S,S)-enantiomers racemic mixtures;

[0113] -A mixture of (R,R)-enantiomers and (S,S)-enantiomers in any other proportion;

[0114] -Pure (R,R) enantiomers; or

[0115] -Pure (S,S)-enantiomers.

[0116] According to one specific embodiment, a compound having Formula I is provided and used in an enantiomer excess (ee) of at least 40%, such as at least 50%, 60%, 70% or 80%, preferably at least 90%, more preferably at least 95%, even more preferably at least 98%, and most preferably at least 99% in the (R,R)-enantiomer form.

[0117] According to one specific embodiment, a compound having Formula I is provided and used in an enantiomer excess (ee) of at least 40%, such as at least 50%, 60%, 70% or 80%, preferably at least 90%, more preferably at least 95%, even more preferably at least 98%, and most preferably at least 99% in the (S,S)-enantiomer form.

[0118] Therefore, according to the present invention, compounds having two chiral centers and possessing formula I can be used in the following form:

[0119] -(R,S)-enantiomers and racemic mixtures of (S,R)-enantiomers;

[0120] -A mixture of (R,S)-enantiomers and (S,R)-enantiomers in any other proportion;

[0121] -Pure (R,S) enantiomers; or

[0122] -Pure (S,R)-enantiomers.

[0123] According to one specific embodiment, a compound having Formula I is provided and used in an enantiomer excess (ee) of at least 40%, such as at least 50%, 60%, 70% or 80%, preferably at least 90%, more preferably at least 95%, even more preferably at least 98%, and most preferably at least 99% in the (R,S)-enantiomer form.

[0124] According to one specific embodiment, a compound having Formula I is provided and used in an enantiomer excess (ee) of at least 40%, such as at least 50%, 60%, 70% or 80%, preferably at least 90%, more preferably at least 95%, even more preferably at least 98%, and most preferably at least 99% in the (S,R)-enantiomer form.

[0125] Therefore, according to the present invention, compounds having two chiral centers and possessing formula I can be used in the following form:

[0126] -A mixture of (R,S)-diastereomers and (S,S)-diastereomers in any proportion.

[0127] According to one specific embodiment, a compound having Formula I is provided and used in diastereomer excess (de) of at least 40%, for example at least 50%, 60%, 70% or 80%, preferably at least 90%, more preferably at least 95%, even more preferably at least 98%, and most preferably at least 99% in the (R,S)-diastereomer form.

[0128] According to one specific embodiment, a compound having Formula I is provided and used in diastereomer excess (de) of at least 40%, for example at least 50%, 60%, 70% or 80%, preferably at least 90%, more preferably at least 95%, even more preferably at least 98%, and most preferably at least 99% in the (S,S)-diastereomer form.

[0129] This applies to mixtures having any other proportions of mixture A (consisting of any proportions of (R,R)-enantiomers and (S,S)-enantiomers) and mixture B (consisting of any proportions of (R,S)-enantiomers and (S,R)-enantiomers).

[0130] This also applies to compounds of formula I with three, four, and five chiral centers.

[0131] In another aspect, the present invention relates to embodiments E.1 to E.275 listed in Table E, which represent the above description with respect to variable X. 1 R 1 Each of the above and preferred combinations of the embodiments defined in the compounds having Formula I as defined below.

[0132]

[0133] Table E:

[0134]

[0135]

[0136]

[0137]

[0138]

[0139]

[0140]

[0141]

[0142]

[0143]

[0144]

[0145] In another aspect, the present invention relates to embodiments E.1 to E.275 listed in Table E, wherein R 2As shown in Example 2.1, and R 3 As illustrated in Example 3.1.

[0146] In another aspect, the present invention relates to embodiments E.1 to E.275 listed in Table E, wherein R 2 As shown in Example 2.2, and R 3 As illustrated in Example 3.1.

[0147] In another aspect, the present invention relates to embodiments E.1 to E.275 listed in Table E, wherein R 2 As shown in Example 2.3, and R 3 As illustrated in Example 3.1.

[0148] In another aspect, the present invention relates to embodiments E.1 to E.275 listed in Table E, wherein R 2 As shown in Example 2.4, and R 3 As illustrated in Example 3.1.

[0149] In another aspect, the present invention relates to embodiments E.1 to E.275 listed in Table E, wherein R 2 As shown in Example 2.1, and R 3 As illustrated in Example 3.2.

[0150] In another aspect, the present invention relates to embodiments E.1 to E.275 listed in Table E, wherein R 2 As shown in Example 2.2, and R 3 As illustrated in Example 3.2.

[0151] In another aspect, the present invention relates to embodiments E.1 to E.275 listed in Table E, wherein R 2 As shown in Example 2.3, and R 3 As illustrated in Example 3.2.

[0152] In another aspect, the present invention relates to embodiments E.1 to E.275 listed in Table E, wherein R 2 As shown in Example 2.4, and R 3 As illustrated in Example 3.2.

[0153] In another aspect, the present invention relates to embodiments E.1 to E.275 listed in Table E, wherein R 2 As shown in Example 2.1, and R 3 As illustrated in Example 3.3.

[0154] In another aspect, the present invention relates to embodiments E.1 to E.275 listed in Table E, wherein R 2 As shown in Example 2.2, and R3 As illustrated in Example 3.3.

[0155] In another aspect, the present invention relates to embodiments E.1 to E.275 listed in Table E, wherein R 2 As shown in Example 2.3, and R 3 As illustrated in Example 3.3.

[0156] In another aspect, the present invention relates to embodiments E.1 to E.275 listed in Table E, wherein R 2 As shown in Example 2.4, and R 3 As illustrated in Example 3.3.

[0157] In another aspect, the present invention relates to embodiments E.1 to E.275 listed in Table E, wherein R 2 and R 3 As illustrated in Example 3.4.

[0158] In another aspect, the present invention relates to embodiments E.1 to E.275 listed in Table E, wherein R 2 and R 3 As illustrated in Example 3.2.

[0159] In another aspect, the present invention relates to embodiments E.1 to E.275 listed in Table E, wherein R 4 As shown in Example 4.1, and R 5 As illustrated in Example 5.1.

[0160] In another aspect, the present invention relates to embodiments E.1 to E.275 listed in Table E, wherein R 4 As shown in Example 4.2, and R 5 As illustrated in Example 5.1.

[0161] In another aspect, the present invention relates to embodiments E.1 to E.275 listed in Table E, wherein R 4 As shown in Example 4.3, and R 5 As illustrated in Example 5.1.

[0162] In another aspect, the present invention relates to embodiments E.1 to E.275 listed in Table E, wherein R 4 As shown in Example 4.4, and R 5 As illustrated in Example 5.1.

[0163] In another aspect, the present invention relates to embodiments E.1 to E.275 listed in Table E, wherein R 4 As shown in Example 4.1, and R 5 As illustrated in Example 5.2.

[0164] In another aspect, the present invention relates to embodiments E.1 to E.275 listed in Table E, wherein R 4 As shown in Example 4.2, and R 5 As illustrated in Example 5.2.

[0165] In another aspect, the present invention relates to embodiments E.1 to E.275 listed in Table E, wherein R 4 As shown in Example 4.3, and R 5 As illustrated in Example 5.2.

[0166] In another aspect, the present invention relates to embodiments E.1 to E.275 listed in Table E, wherein R 4 As shown in Example 4.4, and R 5 As illustrated in Example 5.2.

[0167] In another aspect, the present invention relates to embodiments E.1 to E.275 listed in Table E, wherein R 4 As shown in Example 4.1, and R 5 As illustrated in Example 5.3.

[0168] In another aspect, the present invention relates to embodiments E.1 to E.275 listed in Table E, wherein R 4 As shown in Example 4.2, and R 5 As illustrated in Example 5.3.

[0169] In another aspect, the present invention relates to embodiments E.1 to E.275 listed in Table E, wherein R 4 As shown in Example 4.3, and R 5 As illustrated in Example 5.3.

[0170] In another aspect, the present invention relates to embodiments E.1 to E.275 listed in Table E, wherein R 4 As shown in Example 4.4, and R 5 As illustrated in Example 5.3.

[0171] In another aspect, the present invention relates to embodiments E.1 to E.275 listed in Table E, wherein R 4 and R 5 As illustrated in Example 5.4.

[0172] In another aspect, the present invention relates to embodiments E.1 to E.275 listed in Table E, wherein R 4 and R 5 As illustrated in Example 5.4.

[0173] Preferred embodiments of the present invention are the following compounds IA-1, IA-2, and IA-3. In these formulas, the substituent R 2 R 3 And X independently as defined above or preferably as defined herein:

[0174]

[0175] In particular, considering their intended use, according to one embodiment, compounds IA-1, IA-2, and IA-3 are preferred; these are compiled in Tables 1b to 5b. Furthermore, each group mentioned for a substituent in the tables (independent of the mentioned combination) is a particularly preferred aspect of said substituent.

[0176] Table 1a lists compounds with formulas IA-1, IA-2, and IA-3, where X 2 It is H and R for each individual compound 2 R 3 and X 1 The meaning of the combination corresponds to a row in Table A in each case (compounds IA-1.1aA-1 to IA-1.1aA-48, IA-2.1aA-1 to IA-2.1aA-48, IA-3.1aA-1 to IA-3.1aA-48).

[0177] Table 2a lists compounds with formulas IA-1, IA-2, and IA-3, where X 2 It is F and R for each individual compound 2 R 3 and X 1 The meaning of the combination corresponds to a row in Table A in each case (compounds IA-1.2aA-1 to IA-1.2aA-48, IA-2.2aA-1 to IA-2.2aA-48, IA-3.2aA-1 to IA-3.2aA-48).

[0178] Table 3a lists compounds with formulas IA-1, IA-2, and IA-3, where X 2 It is Cl and R for each individual compound 2 R 3 and X 1 The meaning of the combination corresponds to a row in Table A in each case (compounds IA-1.3aA-1 to IA-1.3aA-48, IA-2.3aA-1 to IA-2.3aA-48, IA-3.3aA-1 to IA-3.3aA-48).

[0179] Table 4a lists compounds with formulas IA-1, IA-2, and IA-3, where X 2 It is CH3 and the R of each individual compound 2 R 3 and X 1 The meaning of the combination corresponds to a row in Table A in each case (compounds IA-1.4aA-1 to IA-1.4aA-48, IA-2.4aA-1 to IA-2.4aA-48, IA-3.4aA-1 to IA-3.4aA-48).

[0180] Table 5a contains compounds with formulas IA-1, IA-2, and IA-3; where X 2 It is OCH3 and R for each individual compound 2 R 3 and X 1 The meaning of the combination corresponds to a row in Table A in each case (compounds IA-1.5aA-1 to IA-1.5aA-48, IA-2.5aA-1 to IA-2.5aA-48, IA-3.5aA-1 to IA-3.5aA-48).

[0181] Table A

[0182]

[0183]

[0184] The compounds of the present invention can be prepared as shown in the following embodiments, wherein, unless otherwise stated, each variable is defined as above for compounds having Formula I. Compounds having Formula I can be prepared according to methods described in the prior art or similar methods. The synthesis utilizes starting materials that are commercially available or can be prepared from readily available compounds according to conventional procedures.

[0185] For example, compound I can be prepared in a palladium-catalyzed cross-coupling reaction of trifluoromethanesulfonate derivative (2) and boric acid derivative (3) in a manner similar to that described in WO 2022243107. Trifluoromethanesulfonate (2) can be prepared as described in WO2022243107.

[0186]

[0187] Compound I and its compositions are suitable as fungicides, effective against a broad spectrum of plant pathogenic fungi, including soil-borne fungi, particularly those from the classes Plasmodiomycetes, Oomycetes, Chytrididae, Zygomycetes, Ascomycetes, Basidiomycetes, and Fungi imperfecti. They can be used in crop protection as foliar fungicides, seed dressing fungicides, and soil fungicides.

[0188] Compound I and its compositions are preferably used to control plant pathogenic fungi in the following: various cultivated plants, such as cereals, such as wheat, rye, barley, triticale, oats, or rice; beets, such as sugar beets or forage beets; fruits, such as pome (apples, pears, etc.), drupes (such as plums, peaches, apricots, cherries), or soft fruits, also known as berries (strawberries, raspberries, blackberries, currants, etc.); legumes, such as lentils, peas, alfalfa, or soybeans; oilseed plants, such as rapeseed, mustard, olives, sunflowers, coconuts, cocoa beans, castor oil plants, oil palms, peanuts, or soybeans; cucurbits, such as squash, cucumbers, or melons; fiber plants, such as cotton, flax, hemp, etc. 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 plants, such as avocados, cinnamon, or camphor; energy and raw material plants, such as corn, soybeans, rapeseed, sugarcane, or oil palm; corn; tobacco; nuts; coffee; tea; bananas; grapevines (table grapes and grape juice vines); hops; turf; stevia (also known as stevia); natural rubber plants; or ornamental and forest plants, such as flowers, shrubs, broad-leaved trees, or evergreen trees (conifers, eucalyptus, etc.); plant propagation materials, such as seeds; and crop materials of these plants.

[0189] More preferably, compound I and its compositions are used to control fungi in the following: field crops, such as potatoes, sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rapeseed, legumes, sunflowers, coffee, or sugarcane; fruits; vines; ornamental plants; or vegetables, such as cucumbers, tomatoes, green beans, or squash.

[0190] The term "plant propagation material" should be understood to refer to all reproductive parts of a plant, such as seeds; and nutrient plant material that can be used for plant propagation, such as cuttings and tubers (e.g., potatoes). This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, buds, and other parts of a plant; including seedlings and young plants that are transplanted after germination or emergence.

[0191] Preferably, plant propagation material is treated with compound I and its compositions for the control of fungi in the following: cereals, such as wheat, rye, barley and oats; rice, corn, cotton and soybeans.

[0192] According to the present invention, all the above-mentioned cultivated plants should be understood to include all species, subspecies, variants, varieties 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., further including dwarf, semi-dwarf and full-dwarf varieties and / or hybrids with reduced height and thicker and shorter stems, such as dwarf maize (also known as "smart maize"), semi-dwarf wheat and dwarf rice.

[0193] Maize, also known as Indian maize or Zea mays, includes all varieties of maize, such as feed maize and sweet maize. According to the present invention, this includes all maize or maize subspecies and / or varieties, particularly floury maize (Zea mays var. amylacea), popcorn maize (Zea mays var. everta), dent maize (Zea mays var. indentata), flint maize (Zea mays var. indurata), sweet maize (Zea mays var. saccharata and var. rugosa), waxy maize (Zea mays var. ceratina), amylomaize (amylomaize), pod maize, or wild maize (Zea mays var. tunicata). tunicata) and striped maize (maize japonica variety (Zea mays var. japonica)).

[0194] Most soybean cultivars can be classified as either indeterminate or determinate, while wild soybean (Glycine soja) (the wild ancestor of soybean) is indeterminate (PNAS [Proceedings of the National Academy of Sciences] 2010, 107 (19) 8563-8568). Indeterminate varieties (maturity group, MG 00 to MG 4.9) are characterized by continuous vegetative growth after flowering begins, while determinate soybean varieties (MG 5 to MG 8) are characterized by having completed most of their vegetative growth by the time flowering begins. According to the present invention, all soybean cultivars or varieties, particularly indeterminate and determinate varieties or varieties, are included.

[0195] The term "cultivated plant" should be understood to include plants that have been modified through mutagenesis or genetic engineering to provide new traits or modify existing traits. Mutagenesis includes random mutagenesis using X-rays or mutagenic chemicals, and also includes targeted mutagenesis to produce mutations at specific loci in the plant genome. Targeted mutagenesis often uses oligonucleotides or proteins such as CRISPR / Cas, zinc finger nucleases, TALENs, or broad-spectrum nucleases. Genetic engineering typically uses recombinant DNA technology to produce modifications in the plant genome that are not readily available in nature through hybridization, mutagenesis, or natural recombination. Typically, one or more genes are integrated into the plant genome to add or improve or modify traits. These integrated genes are also called transgenes, and plants containing such transgenes are called transgenic plants. Plant transformation processes typically produce several transformation events, which differ at the genomic loci in which the transgene has been integrated. Plants containing a specific transgene at a specific genomic locus are often described as containing a specific "event," identified by the name of that specific event. Traits that have been introduced into plants or modified include herbicide tolerance, insect resistance, increased yield, and tolerance to abiotic conditions such as drought.

[0196] Herbicide tolerance has been developed through mutagenesis and genetic engineering. Plants induced to tolerate acetyllactate synthase (ALS) inhibitor herbicides through mutagenesis and breeding are available, for example, under the name Clearfield®. Herbicide tolerance to glyphosate, glufosinate, 2,4-D, dicamba, oxynil herbicides (such as bromobenzonitrile and iodobenzonitrile), sulfonylurea herbicides, ALS inhibitors, and 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors (like isoxaflutole and mesotrione) has been developed through transgenic technology.

[0197] Transgenic organisms providing herbicide tolerance traits include: glyphosate tolerance: cp4 epsps, epspsgrg23ace5, mepsps, 2mepsps, gat4601, gat4621, goxv247; glufosinate tolerance: pat and bar; 2,4-D tolerance: aad-1, aad-12; dicamba tolerance: dmo; benzyl nitrile herbicide tolerance: bxn; sulfonylurea herbicide tolerance: zm-hra, csr1-2, gm-hra, S4-HrA; ALS inhibitor tolerance: csr1-2; and HPPD inhibitor tolerance: hppdPF, W336, avhppd-03.

[0198] 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, VCO-Ø1981-5, 676, 678, 680, 33121, 4114, 59122, 98140, Bt10, Bt176, CBH-351, DBT418, DLL25, MS3, MS6, MZIR098, T25, TC1507, and TC6275. Transgenic soybean events containing herbicide tolerance genes include, but are not limited to, 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, SYHTØH2, W62, W98, FG72, and CV127. Transgenic cotton events containing herbicide tolerance genes include, but are not limited to, 19-51a, 31707, 42317, 81910, 281-24-236, 3006-210-23, BXN10211, BXN10215, BXN10222, BXN10224, MON1445, MON1698, MON88701, MON88913, GHB119, GHB614, LLCotton25, T303-3, and T304-40. Transgenic canola events containing herbicide tolerance genes include, but are not excluded, MON88302, HCR-1, HCN10, HCN28, HCN92, MS1, MS8, PHY14, PHY23, PHY35, PHY36, RF1, RF2, and RF3.

[0199] Transgenic genes providing insect resistance are preferably toxin genes from 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), and vip3Aa20. Additionally, plant-derived transgenic genes, such as those encoding protease inhibitors like CpTI and pinII, can be used. Another approach utilizes transgenic genes such as dvsnf7 to produce double-stranded RNA in plants.

[0200] 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.

[0201] Cultivated plants with increased yields have been produced by using transgenic athb17 (e.g., maize event MON87403) or bbx32 (e.g., soybean event MON87712).

[0202] Cultivated plants with improved oil content have been produced using the following transgenic genes: gm-fad2-1, Pj.D6D, Nc.Fad3, fad2-1A, and fatb1-A (e.g., soybean events 260-05, MON87705, and MON87769).

[0203] Tolerance to abiotic conditions such as drought has been developed through the use of transgenic cspB (maize event MON87460) and Hahb-4 (soybean event IND-ØØ41Ø-5).

[0204] Traits are typically combined by combining genes during transformation events or by combining different events during the breeding process, resulting in cultivated plants with superimposed traits. Preferred combinations of traits include combinations of herbicide tolerance traits from different groups of herbicides, combinations of insect tolerance to different insect species, particularly to Lepidoptera and Coleoptera, combinations of herbicide tolerance with resistance to one or more types of insects, combinations of herbicide tolerance with increased yield, and combinations of herbicide tolerance with tolerance to abiotic conditions.

[0205] Plants containing single or superimposed traits, as well as the genes and events that provide these traits, are well known in the field. For example, detailed information on mutagenic or integrated genes and corresponding events is available from the websites of organizations such as the International Service for the Application of Agri-biotech Applications (ISAAA) (http: / / www.isaaa.org / gmapprovaldatabase) and the Centre for Environmental Risk Assessment (CERA) (http: / / cera-gmc.org / GMCropDatabase). Further information regarding specific events and methods for detecting these events can be found in WO 01 / 031042, WO 01 / 041558, WO 01 / 041558, WO 02 / 036831, WO 11 / 153186, and WO 13 / 003558 for canola events MS1, MS8, RF3, GT73, MON88302, and KK179; and in WO 02 / 034946, WO 03 / 036831, WO 11 / 153186, and WO 13 / 003558 for cotton events MON1445, MON15985, MON531 (MON15985), LLCotton25, MON88913, COT102, 281-24-236, 3006-210-23, COT67B, GHB614, T304-40, GHB119, MON88701, and 81910 ...MON531 (MON15985), MON531 (MON15985), MON531 (MON15985), MON531 (MON15985), MON531 (MON15 02 / 100163、WO 02 / 100163、WO 03 / 013224、WO 04 / 072235、WO 04 / 039986、WO 05 / 103266、WO 05 / 103266、WO 06 / 128573、WO 07 / 017186、WO 08 / 122406, WO 08 / 151780, WO 12 / 134808, WO 13 / 112527;For the corn incident, GA21, MON810, DLL25, TC1507, MON863, MIR604, LY038, MON88017, 3272, 59122, NK603, MIR162, MON89034, 98140, 32138, MON87460, 5307, 4114, MON87427, DAS40278, MON87411, 33121, MON87403, and MON87419 can be found in WO 98 / 044140, US 02 / 102582, US 03 / 126634, WO 04 / 099447, WO 04 / 011601, WO 05 / 103301, WO 05 / 061720, WO 05 / 059103, and WO 06 / 098952、WO 06 / 039376、US 2007 / 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 the rice incident LLRICE06, LLRICE601, LLRICE62, see WO 00 / 026345, WO 00 / 026356, WO 00 / 026345;Furthermore, for soybean events H7-1, MON89788, A2704-12, A5547-127, DP305423, DP356043, MON87701, MON87769, CV127, MON87705, DAS68416-4, MON87708, MON87712, SYHT0H2, DAS81419, DAS81419 x DAS44406-6, MON87751, these can be found in 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, WO10 / 037016, WO11 / 066384, WO11 / 034704, WO12 / 051199, WO12 / 082548, WO13 / 016527, WO13 / 016516, WO14 / 201235.

[0206] The application of compound I and its combinations to cultivated plants can result in effects specific to cultivated plants containing a particular transgene or event. These effects may involve alterations in growth behavior or resistance to biotic or abiotic stresses. Such effects may in particular include increased yield, increased resistance or tolerance to insect, nematode, fungus, bacteria, mycoplasma, virus, or viroid pathogens, as well as early vigor, early or delayed maturity, cold or heat tolerance, and altered amino acid or fatty acid profiles or contents.

[0207] Compound I and its combinations are particularly suitable for controlling the pathogens causing the following plant diseases:

[0208] White rust (A. candida) species on ornamental plants, vegetables (e.g., white rust fungus), and sunflowers (e.g., white rust fungus *A. tragopogonis*); *Albugo* species (white rust disease) on vegetables (e.g., *Albugo* dauci or *Albugo* porri), rapeseed (*Albugo* brassicicola or *Albugo* brassicae), sugar beets (*Albugo* tenuis), fruits (e.g., *Albugo* grandis), rice, soybeans, potatoes, and tomatoes (e.g., *Albugo* solani, *Albugo* or *Albugo* alternata), tomatoes (e.g., *Albugo* solani or *Albugo* alternata), and wheat (e.g., *Albugo* wheat). Alternaria species on *Alternaria triticina* (Alternaria leaf spot); Aphanomyces species on sugar beets and vegetables; Ascochyta species on cereals and vegetables, such as *A. tritici* on wheat (anthracnose) and *A. hordei* on barley; *Aureobasidium zeae* (synonym *Kapatiella zeae*) on maize; Bipolaris and Drechslera species (sexual form: *Cochliobolus* species), such as *D. maydis* on maize (small leaf spot) or *B. zeicola* on maize (large leaf spot), such as *B. zeicola* on cereals (root rot). Sorokiniana) 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 (sexual form: Botryotinia fuckeliana: gray mold) on fruits and berries (e.g., strawberries), vegetables (e.g., lettuce, carrots, celery, and cabbage); Botrytis squamosa or Botrytis squamosa on onion family plants, rapeseed, ornamental plants (e.g., Beliptica), vines, forest plants, and wheat.allii); *Bremia lactucae* on lettuce (downy mildew); *Ceratocystis* species (synonym Ophiostoma) on broadleaf and evergreen trees (rot or wilting), such as *C. ulmi* on elm trees (Dutch elm disease); maize (e.g., gray leaf spot: *C. zeae-maydis*), rice, sugar beets (e.g., *C. beticola*), sugarcane, vegetables, coffee, soybeans (e.g., *C. sojina* or *C. kikuchii*) and *Cercospora* species on rice (Cercospora leaf spot); *Cladobotryum* species (synonym Dactylium) on mushrooms (e.g., *C. mycophilum* (formerly known as *Dactylium dendriticum*)). Dendroides), sexual form: Nectria albertinii, pink parasite (Nectria rosella) synonym Hypomyces rosellus; tomato (e.g. C. fulvum: leaf mold) and Cladosporium species on cereals, such as C. herbarum on wheat (black ear); Claviceps purpurea on cereals (ergot); maize (C. carbonum), cereals (e.g. C. sativus, asexual form: B. sorokiniana) and rice (e.g. C. miyabeanus, asexual form: H. rice long-spore). Species of the genus *Cochliobolus* (asexual form: *Helminthosporium* of *Bipolaris*) on *oryzae* (leaf spot); cotton (e.g., *C. gossypii*), maize (e.g., *C. graminicola*: anthracnose and stem rot), soft fruit, potato (e.g., *C. coccodes*: black spot), bean (e.g., *C. lindemuthianum*), soybean (e.g., *C. truncatum* or *C. gloeosporioides*), vegetables (e.g., *C. lagenarium* or *C. capsici*), and fruits (e.g., *C. oxysporum*).Anthracnose (e.g., *C. coffeanum* or *C. kahawae*) and various crops (*C. gloeosporioides*) species of *Colletotrichum* (sexual form: *Glomerella*) (anthracnose); *Corticium* species, such as *C. sasakii* on rice (sheath blight); *Corynespora cassiicola* on soybeans, cotton, and ornamental plants (leaf spot); *Cycloconium* species, such as *C. oleaginum* on olive trees; fruit trees, vines (e.g., *C. liriodendri*, sexual form: *Neonectria liriodendri*): black foot disease. Foot disease) and Cylindrocarpon species on ornamental plants (e.g., fruit tree canker or young vine decay, sexual type: Nectria or Neonectria species); Dematophoranecatrix on soybean (sexual type: Rosellia necatrix) (root and stem rot); Diaporthe species, such as D. phaseolorum on soybean (damping-off); corn, cereals such as barley (e.g., D. teres, net blotch) and wheat (e.g., D. tritici-repentis, brown spot disease). *Drechslera* species (synonyms: *Helminthosporium*, sexual type: *Pyrenophora*) on rice and turfgrass; *Esca* (dieback, apoplexy) on vines, caused by *Formitiporia punctata* (synonyms: *Phellinus punctata*) and *Formitiporia punctata* (F. truncatum).Caused by *Phaeomoniella mediterranea*, *Phaeomoniella chlamydospora* (formerly *Phaeoacremonium chlamydosporum*), *Phaeoacremonium aleophilum*, and / or *Botryosphaeria obtusa*; *Elsinoe* species on pear fruit (*E. pyri*), soft fruit (*E. veneta*): anthracnose) and vines (*E. ampelina*): anthracnose; *Entyloma oryzae* on rice (leaf smut); *Epicoccum* species on wheat (black mold); sugar beet (*E. beet powdery mildew*). Powdery mildew (e.g., E. pisi) on vegetables such as gourds (e.g., E. cichoracearum), cabbage, rapeseed (e.g., E. cruciferarum); Erysiphe species (powdery mildew) on fruit trees, vines, and ornamental trees (Eutypa lata) (curved spore canker or shoot blight, asexual form: Cytosporinalata, synonym Libertella blepharis); corn (e.g., E. maize large leaf spot). Species of the genus *Exserohilum* (synonym *Helminthosporium*) on *turcicum*; species of the genus *Fusarium* (sexual form: *Gibberella*) on various plants (causing wilting, root or stem rot), such as *F. graminearum* or *F. culmorum* on cereals (e.g., wheat or barley) (causing root rot, scab, or head blight), *F. oxysporum* on tomatoes, *F. solani* (a soybean-specific *F. sp. glycines*, a new synonym for soybean sudden death syndrome pathogen *F. virguliforme*) and *F. tucumaniae* and *F. brasiliense* (both causing sudden death syndrome) on soybeans, and *F. verticillata* on maize.verticillioides; Gaeumannomyces graminis (take-all) on cereals (e.g., wheat or barley) and maize; Gibberella species on cereals (e.g., G. zeae) and rice (e.g., G. fujikuroi: Bakanae disease); Glomerella cingulata on vines, pears and other plants and G. gossypii on cotton; Grainstaining complex on rice; Guignardia bidwellii (black rot) on vines; Gymnosporangium species on Rosaceae and juniper, such as G. brown glomerulosa on pears. sabinae (rust); Helminthosporium species (synonyms: Drechslera, sexual form: Cochliobolus) on corn, cereals, potatoes, and rice; Hemileia species, such as H. vastatrix on coffee (coffee leaf rust); Isariopsis clavispora (synonyms: Cladosporium vitis) on vines; Macropomina phaseolina (synonyms: Macropomina phaseoli) on soybeans and cotton (root and stem rot); Microdochium (synonyms: Fusarium) on cereals (e.g., wheat or barley) (powdery mildew); Microsphaera on soybeans. (Powdery mildew); Monilinia species on drupes and other Rosaceae plants, such as *M. laxa*, *M. fructicola*, and *M. fructigena* (synonyms: *Monilia* species: flower rot and branch blight, brown rot); Mycosphaerella species on cereals, bananas, soft fruits, and peanuts, such as *M. gracilis* on wheat.*Zymoseptoria tritici* (asexual form: *Zymoseptoria tritici*, formerly known as *Septoria tritici*: *Zymoseptoria tritici* leaf spot), or *M. fijiensis* (synonym *Pseudocercospora fijiensis*: black Sigatoka disease) and *M. musicola* on bananas, *M. arachidicola* (synonym *M. arachidis* or *Cercospora arachidis*) and *M. berkeleyi* on peanuts, *M. pisi* on peas, and *M. brassiciola* on *Brassicae*; cabbage (e.g., *P. brassicae*), rapeseed (e.g., *P. parasiticus*). Downy mildew species (Peronospora) on parasitica, onions (e.g., P. destructor), tobacco (P. tabacina), and soybeans (e.g., P. manshurica); soybean rust fungi such as P. meibomiae 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. beetroot on sugar beets. betae (root rot, leaf spot, and damping-off), and P. zeae-maydis (synonym Phyllosticazeae) on maize; Phomopsis species on sunflowers, vines (e.g., P. viticola: vine and leaf spot) and soybeans (e.g., stem rot: P. phaseoli, sexual form: Diaporthe phaseolorum); Physoderma maydis (brown spot) on maize; Phytophthora species on various plants (wilt, root, leaf, fruit, and stem rot), such as red peppers and gourds (e.g., Phytophthora capsici).*Phytophthora capsici*, soybeans (e.g., *P. megasperma*, synonym *P. sojae*), potatoes and tomatoes (e.g., *P. infestans*: late blight), and broadleaf trees (e.g., *P. ramorum*: sudden death of oak trees); *Plasmodiophora brassicae* (club root) on cabbage, rapeseed, radish, and other plants; *Plasmopara* species, such as *P. viticola* (grape downy mildew) on vines and *P. halstedii* on sunflowers; *Podosphaera* species (powdery mildew) on Rosaceae plants, hops, pome, and soft fruits, such as *P. white podosphaera* on apples. *Pseudocercosphaera* on gourds and *P. xanthii* on gourds; *Polymyxa* species on cereals such as barley and wheat (*P. graminis*) and sugar beets (*P. betae*), and viral diseases transmitted by these; *Pseudocercosporella herpotrichoides* (synonyms *Oculimaculayallundae*, *O. acuformis*: eye spot, sexual form: *Tapesia yallundae*) on cereals such as wheat or barley; *Pseudoperonospora* (downy mildew) on various plants, such as *P. cubensis* on gourds or *P. humili* on hops; *Pseudopezicula tracheiphila* (red fire disease) on vines. Disease) or rotbrenner, asexual form: genus *Phialophora*; species of the genus *Puccinia* (rust diseases) on various plants, such as *P. triticina* (brown rust or leaf rust) on cereals (such as wheat, barley, or rye), *P. striiformis* (stripe rust or yellow rust), *P. hordei* (dwarf rust) on barley, *P. graminis* (stem rust or black rust) or *P. recondita* (brown rust or leaf rust), *P. kuehnii* (citrus rust) on sugarcane, and *P. asparagus* species on asparagus.asparagi); species of the genus *Pyrenopeziza*, such as *P. brassicae* on rapeseed; *Pyrenophora tritici-repentis* (asexual form: *Drechslera tritici-repentis*) (brown spot) on wheat or *P. teres* (net blotch) on barley; species of the genus *Pyricularia*, such as *P. oryzae* (sexual form: *Magnaporthe grisea*) on rice, and *P. grisea* on turfgrass and cereals; species of the genus *Pythium* (damping-off) on turfgrass, rice, corn, wheat, cotton, rapeseed, sunflower, soybean, sugar beet, vegetables, and many other plants (e.g., *P. truncatula*). *Pythium ultimum* or *P. aphanidermatum* and *P. oligandrum* on mushrooms; *Ramularia* species, such as *R. collo-cygni* on barley (*Ramularia* leaf spot, physiological leaf spot), *R. areola* on cotton (sexual form: *Mycosphaerella areola*), and *R. beticola* on sugar beets; *Rhizoctonia* species on cotton, rice, potato, bulrush, corn, rapeseed, sugar beets, vegetables, and many other plants, such as *R. solani* on soybean (*Rhizoctonia* root and stem rot), and *R. solani* on rice. *Rhizopus solani* (sheath blight) or *Rhizopus cerealis* (rhizopus leaf blight) on wheat or barley; *Rhizopus stolonifer* (black mold, soft rot) on strawberries, carrots, cabbages, vines, and tomatoes; *Rhynchosporium secalis* and *R. commune* (scald) on barley, rye, and triticale; *Sarocladium oryzae* and *S. attenuatum* (sheath rot) on rice; *S. minor* and *S. sclerotiorum* on vegetables and field crops such as rapeseed, sunflower (e.g., *S. sclerotiorum*) and soybeans, and *S. sclerotinia* species (stem rot or white mold); *S. uniformis* on soybeans, peanuts, vegetables, corn, cereals, and ornamental plants.*Septoria* species found on various plants, such as *S. glycines* (for brown spot disease) on soybeans, *S. tritici* (for wheat fermentation *S. tritici*, for ... turcicum) and Setosphaeria species on turfgrass (leaf blight); maize (e.g., S. reiliana, synonym Ustilago reiliana: smut), Sphacelotheca species on sorghum and sugarcane (smut); Sphaerotheca fuliginea on gourd (synonym Podosphaera xanthii: powdery mildew); Spongosspora subterranea on potato (powdery mildew) and viral diseases transmitted by it; Stagonospora species on cereals, such as S. nodorum on wheat (spot blight, sexual form: Leptosphaeria) nodorum [synonyms: Phaeosphaerianodorum, Septoria nodorum]; syncytrium endobioticum on potatoes (potato canker); species of the genus Taphrina, such as T. deformans on peaches (leaf curl) and T. pruni on plums (plumpocket); species of the genus Thieviopsis on tobacco, pome, vegetables, soybeans, and cotton (black root rot), such as T. thielaviopsis.Basicola (synonym: Chalara elegans); Tilletia species on grains (common bunt or stinking smut), such as T. tritici (synonym: T. caries, wheat bunt) and T. controversa (wheat bunt); Trichoderma harzianum on mushrooms; Typhula incarnata (grey snow mold) on barley or wheat; Urocystis species, such as U. occulta (stem smut) on rye; vegetables such as beans (e.g., U. appendiculatus, synonym: U. phaseoli), and sugar beets (e.g., U. appendiculatus). Rusts caused by *Uromyces* species on beans (e.g., *U. vignae*, *U. pisi*, *U. viciae-fabae*, and *U. fabae*) and dried beans (e.g., *U. vignae*, *U. pisi*, *U. viciae-fabae*, and *U. fabae*); and loose smut (*U. nuda* and *U. avaenae*), maize (e.g., *U. maydis*: maize smut), and sugarcane (*Ustilago* species). Scab; species of *Venturia* on apples (e.g., *V. inaequalis*) and pears (scab); and species of *Verticillium* on various plants such as fruits and ornamental plants, vines, soft fruits, vegetables, and field crops (wilt), such as *V. longisporum* on rapeseed, *V. dahliae* on strawberries, rapeseed, potatoes, and tomatoes, and *V. fungicola* on mushrooms; and *Syngonium spp.* on cereals.

[0209] Compound I and its combinations are particularly suitable for controlling pathogens of the following plant diseases: rust diseases on soybeans and cereals (e.g., *Puccinia tritici* and *P. striiformis* rust on soybeans; *Puccinia tritici* and *P. striiformis* rust on wheat); mildew diseases on specialty crops, soybeans, rapeseed, and sunflowers (e.g., *Botrytis cinerea* on strawberries and vines; *Sclerotium rolfsii*, *Sclerotium sclerotiorum*, and *S. rolfsii* on rapeseed, sunflower, and soybeans); and Fusarium diseases on cereals (e.g., *Fusarium oxysporum* on wheat). *Culmorum* and *Fusarium* species of the Poaceae family); downy mildew on specialty crops (e.g., *Monosporium variegatum* on vines, *Phytophthora infestans* on potatoes); powdery mildew on specialty crops and cereals (e.g., *Hypericum variegatum* on vines, various *Effective* species on specialty crops, *Brucella variegata* on cereals); and leaf spot on cereals, soybeans, and maize (e.g., *Syneomyces leucopterus* and *Syneomyces glenophorum* on cereals, *Syneomyces sacchari* on soybeans, *Cercospora* species on maize and soybeans).

[0210] It has been observed that plant pathogenic fungal communities, which are clearly composed of non-resistant strains, can readily develop resistance. These compounds can also be applied under conditions that completely prevent the formation of resistance and the spread of resistant strains. In this respect, it is useful that they also possess strong activity against non-resistant plant pathogenic fungi.

[0211] Various fungicide-resistant strains of plant pathogenic fungi have been reported, with resistance to one or more fungicides from various modes of action observed through target site mutations in the genes of the corresponding proteins (e.g., QoI (C3, see www.frac.info according to FRAC convention), quinone exo-labeled styracin binding subsite inhibitors (QoSI; C8) and quinone intra-labeled inhibitors (QiI; C4): CytB target protein; sterol demethylation (DMI, G1): Cyp51 / Erg11; carboxylamides (CAA, H5): CesA3; SDHI (C2): SdhB, SdhC, and SdhD; dicarboxylimides (E3): Os-1 (including Bos1, Daf1, etc.); ketoreductase inhibitors (KRI; Class III SBI; G3): Erg27; and oxidized sterol binding protein inhibitors (OSBPI; F9): ORP1).

[0212] Table M indicates examples of mutation sites in genes encoding such target proteins that result in single amino acid exchanges, deletions, or insertions listed in the corresponding target protein sequence, thereby conferring resistance to certain fungicides in plant pathogenic fungi (see also Pest Management Science 72(8) 2016: 1449-1459).

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219]

[0220]

[0221]

[0222]

[0223] Therefore, Compound I is particularly useful for controlling fungicide-resistant strains of plant pathogenic fungi as described in Table M. Such strains may possess one or more resistances derived from one or more mutations (including, but not limited to, mutations listed in Table M) of one or more genes encoding target proteins of various fungicides, and / or resistance derived from overexpression of the corresponding target proteins. Compound I can also be used against dihydroorotate dehydrogenase inhibitor-resistant plant pathogenic fungi, as described in the scope of WO2024084028.

[0224] Furthermore, some fungal strains may have developed so-called multidrug resistance, ultimately leading to broad cross-resistance to many structurally and functionally unrelated compounds. "Multidrug resistance" (MDR), also known as "multidirectional resistance" (PDR), describes a resistance phenomenon typically caused by the overexpression of certain membrane transport proteins, resulting in increased activity of efflux pumps that export certain substrates (e.g., mycotoxins and fungicidal compounds). Examples of such membrane transport proteins include ATP-binding cassette (ABC) transporters and the major cotransporter superfamily (MFS) transporters. Overexpression of membrane transport proteins can be confirmed, for example, by measuring the amount of the transporter or its corresponding mRNA. The measured mRNA amount can be, for example, 2, 5, 20, up to 100 times or more, relative to the mRNA amount of the corresponding fungicide-sensitive wild-type fungus.

[0225] Compound I of the present invention can be used to control plant diseases caused by multidrug-resistant (MDR) fungi. MDR fungi can also possess one or more types of resistance derived from one or more mutations (including, but not limited to, mutations listed in Table M) in one or more genes encoding target proteins of various fungicides, and / or resistance derived from overexpression of the target proteins. Therefore, Compound I is also particularly useful for controlling such MDR fungi.

[0226] Compound I and its compositions are also suitable for the prevention and control of harmful microorganisms in the protection of stored products or harvests and in the protection of materials.

[0227] The term "stored product or harvest" should be understood to refer to natural substances of plant or animal origin and their processing forms desired for long-term preservation. Plant-derived stored products, such as stems, leaves, tubers, seeds, fruits, or grains, can be preserved in their freshly harvested state or through processing methods such as pre-drying, moistening, crushing, grinding, pressing, or baking (processing also known as post-harvest treatment). Timber also falls under the definition of stored products, whether in log form, such as construction timber, transmission towers, and fences, or in finished product form, such as furniture or objects made of wood. Animal-derived stored products are hides, leather, fur, hair, etc. Preferably, "stored product" should be understood to refer to natural substances of plant origin and their processing forms, more preferably fruits and their processing forms, such as pome, stone fruit, soft fruit, and citrus fruits and their processing forms, wherein the application of compound I and its combinations can also prevent adverse effects such as rot, discoloration, or mold.

[0228] 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, coolant lubricants, fibers, or fabrics from contamination and damage by harmful microorganisms such as fungi and bacteria.

[0229] When used for the protection of materials or stored products, the amount of active substance applied depends on the type of application and the desired effect. Typically, the amount applied for the protection of materials is 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active substance per cubic meter of treated material.

[0230] Compound I and its compositions can be used to improve plant health. The present invention also relates to a method for improving plant health by treating plants, their propagation material, and / or the sites where plants are growing or will grow, respectively, with effective amounts of Compound I and its compositions.

[0231] The term "plant health" should be understood as referring to the condition of plants and / or their products, determined by multiple indicators, individually or in combination, 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. These plant health indicators may be interdependent or mutually influential.

[0232] Compound I is used as is or in combination form to treat fungi with an effective amount of the active substance, protecting plants, plant propagation material (such as seeds), soil, surfaces, materials, or rooms from fungal infection. Application can be carried out before or after the plants, plant propagation material (such as seeds), soil, surfaces, materials, or rooms are infected with fungi.

[0233] Agricultural chemical compositions contain a fungicide-effective amount of compound I. The term "fungicide-effective amount" refers to the amount of a composition or compound I sufficient to control harmful fungi on cultivated plants, or in the protection of stored products or harvests, or in the protection of materials, without causing substantial damage to the treated plants, stored products or harvests, or treated materials. This amount can vary widely and depends on various factors such as the fungal species to be controlled, the treated cultivated plants, stored products, harvests or materials, climatic conditions, and the specific compound I used.

[0234] Plant propagation material may be preventively treated with compound I itself or a composition containing at least one compound I during or before planting or transplanting.

[0235] When used for plant protection, the amount of 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, depending on the type of effect desired.

[0236] In the treatment of plant propagation material (such as seeds), for example by dusting, coating or soaking, every 100 kg of plant propagation material (preferably seeds) requires an amount of active substance that is typically 0.1 to 1000 g, preferably 1 to 1000 g, more preferably 1 to 100 g and most preferably 5 to 100 g.

[0237] Users typically apply agricultural chemical compositions using pre-dose devices, backpack sprayers, spray cans, spray aircraft, or irrigation systems. Generally, the agricultural chemical composition is prepared to the desired application concentration using water, buffer solutions, and / or additional adjuvants, thus yielding a ready-to-use spray or agricultural chemical composition according to the invention. Typically, 20 to 2000 liters, preferably 50 to 400 liters, of ready-to-use spray are applied per hectare of usable agricultural area.

[0238] Compound I and compositions containing them can be applied in conjunction with or utilizing smart agriculture technologies such as precision agriculture, remote and near-field imaging and image recognition, or smart agriculture site management programs. Such technologies typically include models, such as computer programs, that support users by considering information from various sources to increase the quality and yield of harvested materials, reduce pest damage, including the prediction of pest stress and the intelligent application of crop protection products, ensure environmental protection, support rapid and reliable agronomic decision-making, reduce the use of fertilizers and crop protection products, reduce product residues in consumer products, increase the spatial and temporal accuracy of agronomic measures, automate processes, and enable traceability of measures. Commercially available systems that include agronomic models include, for example, FieldScripts™ (The Climate Corporation), Xarvio™ (BASF), and AGLogic™ (John Deere).

[0239] The information inputs for these models include, but are not limited to, soil data, information about plants (including crops and / or unwanted vegetation) currently growing in or likely to grow in the area of ​​interest, weather information, information about the location of the area and information that can be directly derived from it, information about pest stress, information about beneficial organisms (including predicted and current ones), and / or historical information on any of the above.

[0240] Information that can be used in precision agriculture can be based on input from at least one user, accessed from external data sources and databases, or based on sensor data. Data sources typically include short-range detection systems, such as soil sensors, and remote sensing, which can be achieved, for example, through imaging by unmanned aerial vehicles such as drones or satellites. Sensors can be included in Internet of Things (IoT) systems and can be directly or indirectly connected to processing units, for example via wireless networks and / or cloud applications. Typically, at least one processing unit will take this information into account and use it to provide recommendations and generate control signals.

[0241] Typical technologies used in smart agriculture include automated control robots (such as tractors, harvesters, and drones), artificial intelligence (such as machine learning), imaging technology (such as image segmentation), big data analytics, model generation, cloud computing, and machine-to-machine communication.

[0242] Precision agriculture, such as precision farming, is characterized by the targeted application of active ingredients like pesticides, plant growth regulators, fertilizers, and / or water, analyzed spatially and / or temporally. This includes variations in application rates at agronomic sites, regions, or specific locations, and variations in the targeted planting or sowing of desired plant propagation material at agronomic sites in a spatially and / or temporally analyzed manner. Precision agriculture typically involves using geolocation technologies like GPS to acquire information about the location and boundaries of areas of interest, the application equipment used, the sensors employed, and the recorded data, and to control the actions of agricultural vehicles, such as spraying. By combining geolocation data with (digital) maps, it becomes possible to perform (semi-)automated agricultural practices at locations of interest, such as through the use of (semi-)automated spraying or sowing equipment.

[0243] Precision agriculture typically includes the application of smart spraying equipment, such as spot spraying; and precision spraying on farms, such as via irrigation systems, tractors, robots, helicopters, airplanes, and unmanned aerial vehicles (UAVs). Such equipment typically includes input sensors (e.g., cameras) and a processing unit configured to analyze input data and to provide recommendations or decisions based on the analysis of the input data to apply Compound I or compositions containing them to agronomic sites, such as soil, crop plants, or to control pests in a specific and precise manner. For example, pest detection, identification, and / or classification can be performed in images acquired by a camera. Such identification and / or classification can utilize image processing algorithms that may employ artificial intelligence (e.g., machine learning algorithms) or decision trees. In this way, Compound I or compositions described herein can be applied only at the desired location, time point, and dosage rate.

[0244] Compound I, its N-oxide, and salt can be converted into commonly used types of agrochemical compositions, such as solutions, emulsions, suspensions, dusts, powders, pastes, granules, tablets, capsules, and mixtures thereof. Examples of composition types (see also "Catalogue of pesticide formulation types and international coding system", Technical Monograph, Vol. 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), insecticides (e.g., LN), and gel formulations (e.g., GF) for treating plant propagation materials (such as seeds). These compositions are prepared in known ways, such as those described in: 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 an adjuvant and at least one compound I.

[0245] Suitable additives include solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, auxiliary agents, solubilizers, penetration enhancers, protective colloids, adhesives, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, antifreeze agents, antifoaming agents, colorants, viscous agents, and binders.

[0246] Suitable solvents and liquid carriers are water and organic solvents, such as medium to high boiling point mineral oil fractions, such as kerosene and diesel; oils of vegetable or animal origin; aliphatic, cyclic, and aromatic hydrocarbons, such as toluene, paraffin, tetrahydronaphthalene, and alkylnaphthalene; alcohols, such as ethanol, propanol, butanol, benzyl alcohol, cyclohexanol, and glycol; DMSO; ketones, such as cyclohexanone; esters, such as lactates, carbonates, fatty acid esters, and γ-butyrolactone; fatty acids; phosphonates; amines; amides, such as N-methylpyrrolidone and fatty acid dimethylamide; and mixtures thereof.

[0247] Suitable solid carriers or fillers are mineral soils, such as silicates, silica gel, talc, kaolin, limestone, lime, chalk, clay, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, and magnesium oxide; polysaccharides, such as cellulose and starch; fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, and urea; and plant-derived products, such as cereal flour, bark flour, wood flour, nut shell flour, and mixtures thereof.

[0248] Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic, and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifiers, dispersants, solubilizers, wetting agents, penetration enhancers, protective colloids, or auxiliaries. Examples of surfactants are listed in McCutcheon's, Volume 1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International or North American edition).

[0249] Suitable anionic surfactants are alkali metal salts, alkaline earth metal salts, or ammonium salts of sulfonates, sulfates, phosphates, and carboxylates, and mixtures thereof. Examples of sulfonates are alkylaryl sulfonates, diphenyl sulfonates, α-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecylbenzene and tridecylbenzene, sulfonates of naphthalene and alkylnaphthalenes, sulfosuccinates, or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids, oils, ethoxylated alkylphenols, alcohols, ethoxylated alcohols, or fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates and carboxylated alcohols or alkylphenol ethoxylates.

[0250] 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 by 1 to 50 equivalents. Ethylene oxide and / or propylene oxide can be used for alkoxylation, with ethylene oxide being preferred. Examples of N-substituted fatty acid amides are fatty acid glucosamides or fatty acid chain alkanolamides. Examples of esters are fatty acid esters, glycerides, or monoglycerides. Examples of glycosyl surfactants are sorbitan, ethoxylated sorbitan, sucrose and glucose esters, or alkyl polyglucosides. Examples of polymeric surfactants are homologs or copolymers of vinylpyrrolidone, vinyl alcohol, or vinyl acetate.

[0251] 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 AB or ABA type block polymers containing polyethylene oxide and polypropylene oxide blocks, or ABC type block polymers containing alkanols, polyethylene oxide, and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali metal salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamine or polyvinylamine.

[0252] Suitable adjuvants are compounds that possess negligible or no biocidal activity themselves and enhance the biological performance of compound I against the target. Examples include surfactants, mineral or vegetable oils, and other adjuvants, such as those listed in Knowles, Adjuvants and Additives, Agrow Reports DS256, T&F Informa UK, 2006, Chapter 5. Suitable thickeners are polysaccharides (e.g., xanthan gum, carboxymethyl cellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates. Suitable bactericides are bronopol and isothiazolinone derivatives, such as alkylisothiazolinones and benzisothiazolinones. Suitable antifreeze agents are ethylene glycol, propylene glycol, urea, and glycerin. Suitable defoamers are silicones, long-chain alcohols, and salts of fatty acids. Suitable colorants (e.g., red, blue, or green) are low-water-soluble pigments and water-soluble dyes. Examples include inorganic colorants (e.g., iron oxide, titanium dioxide, ferric hexacyanate ferrite) and organic colorants (e.g., alizarin colorants, azo colorants, and phthalocyanine colorants). Suitable thickeners or binders are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, polyacrylates, biowaxes or synthetic waxes, and cellulose ethers.

[0253] Agricultural chemical compositions typically contain, by weight, an active substance (e.g., at least one compound I) at a concentration between 0.01% and 95%, preferably between 0.1% and 90%, more preferably between 1% and 70%, and particularly between 10% and 60%. Agricultural chemical compositions typically contain, by weight, at least one adjuvant at a concentration between 5% and 99.9%, preferably between 10% and 99.9%, more preferably between 30% and 99%, and particularly between 40% and 90%. The active substance (e.g., compound I) is used with a purity of 90% to 100%, preferably 95% to 100% (based on NMR spectra).

[0254] For the purpose of treating plant propagating material, especially seeds, seed treatment solutions (LS), suspension emulsions (SE), flowable concentrates (FS), dry treatment powders (DS), water-dispersible powders (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC), and gels (GF) are commonly used. After dilution by 2 to 10 times, the concentration of the active ingredient in the ready-to-use formulation of the compositions under discussion is 0.01% to 60% by weight, preferably 0.1% to 40%. Application can be carried out before or during sowing. Methods for applying compound I and its compositions to plant propagating material, especially seeds, include seed dressing, coating, granulation, dusting, soaking, and furrow application. Preferably, compound I or its compositions are applied to the plant propagating material by methods that do not induce germination, such as seed dressing, granulation, coating, and dusting.

[0255] Various types of oils, wetting agents, adjuvants, fertilizers, or micronutrients, as well as other pest control agents (e.g., fungicides, growth regulators, herbicides, insecticides, safeners) can be added as premixes to Compound I or its compositions, or added only before use (tank mix). These agents can be blended with the compositions according to the invention at a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.

[0256] Pesticides are generally chemical or biological agents (such as pest-killing active ingredients, compounds, compositions, viruses, bacteria, antimicrobial agents, or disinfectants) that prevent, disable, kill, or otherwise thwart pests through their effects. Target pests can include insects, plant pathogens, weeds, mollusks, birds, mammals, fish, nematodes (roundworms), and microorganisms that damage property, cause disturbances, spread diseases, or act as vectors for diseases. The term "pesticide" also includes plant growth regulators that alter the expected growth, flowering, or reproductive rate of plants; defoliants that cause leaves or other foliage to fall off the plant, generally promoting harvest; desiccants that promote the drying of living tissues, such as unwanted above-ground parts of plants; plant activators that activate plant physiological functions to defend against certain pests; safeners that reduce the unwanted herbicidal effects of pesticides on crop plants; and plant growth promoters that affect plant physiological functions, such as enhancing plant growth, biomass, yield, or any other quality parameter of the harvestable product of the crop plant.

[0257] Biopesticides are defined as pesticides based on microorganisms (bacteria, fungi, viruses, nematodes, etc.) or natural products (compounds, such as metabolites, proteins, or extracts from biological or other natural sources) (US Environmental Protection Agency: http: / / www.epa.gov / pesticides / biopesticides / ). Biopesticides fall into two main categories: microbial and biochemical pesticides.

[0258] (1) Microbial pest control agents consist of bacteria, fungi, or viruses (and typically include metabolites produced by bacteria and fungi). Insecticidal nematodes are also classified as microbial pest control agents, although they are multicellular.

[0259] (2) Biochemical pesticides are naturally occurring substances that are relatively nontoxic to mammals, and are used to control pests or provide other crop protection purposes as defined below.

[0260] In many cases, mixing compound I, used as a fungicide, or compositions containing it, with other fungicides results in the broadening of the fungicidal activity spectrum or the prevention of the development of fungicide resistance. Furthermore, in many cases, synergistic effects (synergistic mixtures) are achieved.

[0261] The following list of biocides II that can be used in combination with compound I is intended to illustrate possible combinations, but does not limit them:

[0262] A) Respiratory depressants

[0263] -in Q oComplex III inhibitors at the site (QoI, C3, FRAC convention; www.frac.info): azoxystrobin (A.1.1), fenoxystrobin (A.1.2), eugenol (A.1.3), azoxystrobin (A.1.4), tebufenoxam (A.1.5), tebufenoxam (A.1.6), fenoxystrobin (A.1.7), flufenoxystrobin (A.1.8), azoxystrobin (A.1.9), mandestrobin. (A.1.10), fenoxyfen (A.1.11), oxadiazon (A.1.12), azoxystrobin (A.1.13), pyraclostrobin (A.1.14), azoxystrobin (A.1.15), azoxystrobin (A.1.16), oxadiazon (A.1.17), 2-(2-(3-(2,6-dichlorophenyl)-1-methyl-allylaminooxymethyl)-phenyl)-2-methoxyimino-N-methylacetamide (A.1.18), pyraclostrobin (A.1.19), chlorpyrifos (triclopyricarb / chlorodincarb) (A.1.20), Oxazolidinone (A.1.21), Imidacloprid (A.1.21), Methyl-N-[2-[(1,4-dimethyl-5-phenyl-pyrazol-3-yl)oxymethyl]phenyl]-N-methoxy-carbamate (A.1.22), Tetracyclazole (A.1.25; member of MoA subgroup A), (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino- N,3-Dimethyl-pentan-3-enamide (A.1.34), (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pentan-3-enamide (A.1.35), pyrimethanil (A.1.36), pyraclostrobin (A.1.37), 2-(o-((2,5-dimethylphenyl-oxymethylene)phenyl)-3-methoxymethyl acrylate (A.1.38);

[0264] -in Q i Complex III inhibitors at the site (QiI, C4): cyazofamid (A.2.1), indoxofensulfuron (A.2.2), 2-methylpropionic acid [(6S,7R,8R)-8-benzyl-3-[(3-hydroxy-4-methoxy-pyridin-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonon-7-yl] ester (A.2.3), fenpicoxamid (A.2.4), pyridine (A.2.5), metarylpicoxamid (A.2.6);

[0265] - Complex II inhibitors (SDHI, C2): Benzac-methyl (A.3.1), Benzoflufenicol (A.3.2), Bifenazate (A.3.3), Cyclopyr (A.3.4), Mancozeb (A.3.5), Mefenoxam (A.3.6), Fluopyram (A.3.7), Fluopyram (A.3.8), Fluopyram (A.3.9), Furazolidone (A.3.10), Isopropylthiamethoxam (A.3.11), Pyraclostrobin (A.3.12), Mefenoxam (A.3.13), Oxycarboxim (A.3.14), Fluopyram (A.3.15), Pyraclostrobin (A.3.16), Fluopyram (A.3.17) .3.17), bifenazate (A.3.18), fluoxastrobin (A.3.19), chlorothalonil (A.3.20), thifluzamide (A.3.21), inpyrfluxam (A.3.22), pyrapropoyne (A.3.23), fluoxastrobin (A.3.28), N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-5-fluoro-1-methyl-pyrazole-4-carboxamide (A.3.29), (E)-2-[2-[(5-cyano-2-methyl-phenoxy)methyl]phenyl]-3-methoxy-prop-2- Methyl acrylate (A.3.30), isoflucypram (A.3.31), 2-(difluoromethyl)-N-(1,1,3-trimethyl-indane-4-yl)pyridine-3-carboxamide (A.3.32), 2-(difluoromethyl)-N-[(3R)-1,1,3-trimethyl-indane-4-yl]pyridine-3-carboxamide (A.3.33), 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indane-4-yl)pyridine-3-carboxamide (A.3.34), 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indane-4-yl]pyridine-3-carboxamide Amines (A.3.35), 2-(difluoromethyl)-N-(1,1-dimethyl-3-propyl-indamino-4-yl)pyridine-3-carboxamide (A.3.36), 2-(difluoromethyl)-N-[(3R)-1,1-dimethyl-3-propyl-indamino-4-yl]pyridine-3-carboxamide (A.3.37), 2-(difluoromethyl)-N-(3-isobutyl-1,1-dimethyl-indamino-4-yl)pyridine-3-carboxamide (A.3.38), 2-(difluoromethyl)-N-[(3R)-3-isobutyl-1,1-dimethyl-indamino-4-yl]pyridine-3-carboxamide (A.3.39), trifluoropyridineamine (A.3.24);

[0266] - Other respiratory depressants: diflubenzuron (A.4.1); nitrophenyl derivatives: acaricides (A.4.2), fenpropathrin (A.4.3), fenpropathrin (A.4.4), fluazinam (A.4.5), fenpropathrin (A.4.6), pyrimethanil (A.4.7); organometallic compounds: triphenyltin salts, such as triphenyltin acetate (A.4.8), triphenyltin chloride (A.4.9), or triphenyltin hydroxide (A.4.10); silthiamethoxam (A.4.11);

[0267] - Quinone-extraquinone inhibitor binding type (QoSI; C8): Azoxystrobin (A.5.1);

[0268] B) Sterol biosynthesis inhibitors (SBI fungicides)

[0269] -C14 demethylase inhibitors (DMI, G1): Triazoles: Penticazole (B.1.1), Bifenthrin (B.1.2), Fenoxacillin (B.1.3), Cycloconazole (B.1.4), Oxadiazon (B.1.5), Tebuconazole (B.1.6), Tebuconazole-M (B.1.7), Flutriafol (B.1.8), Cyproconazole (B.1.9), Fluquinazole (B.1.10), Flusilazole (B.1.11), Tebuconazole (B.1.12), Hexaconazole (B.1.13), Ammonium oxychloride (B.1.14), Izoxystrobin (B.1.15), Imidacloprid (B.1.17), Cyproconazole (B.1.18), Oxamidazole (B.1.19), Paclobutrazol (B.1.20), Tebuconazole (B.1.21), Propiconazole (B.1.22), Prothioconazole (B.1.23), Silosovirazole (B.1.24), Tebuconazole (B.1.25), Flufenoxuron (B.1.26) .1.26), triadimefon (B.1.27), azoxystrobin (B.1.28), cymoxanil (B.1.29), uniconazole (B.1.30), 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(2,2,2-trifluoroethoxy)phenyl]-2-pyridyl]prop-2-ol (B.1.31), 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(trifluoromethoxy)phenyl]-2-pyridyl]prop-2-ol (B.1.32), fluopyram (B.1.33), isothiazine Fluopyram (ipfentrifluconazole) (B.1.37), chlorfenapyr (B.1.38), (2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)prop-2-ol, (2S)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazol-1-yl)prop-2-ol, 2-(chloromethyl)-2-methyl-5-(p-tolylmethyl)-1-(1,2,4-triazol-1-ylmethyl)cyclopentanol (B.1.43); imidazoles: acetamiprid (B.1.43) .1.44), isoprothiolane (B.1.45), prochloraz (B.1.46), fluconazole (B.1.47); pyrimidines, pyridines, piperazines: chlorophenylpyrimidinol (B.1.49), pyridabenoxime (B.1.50), azithromycin (B.1.51), [3-(4-chloro-2-fluoro-phenyl)-5-(2,4-difluorophenyl)isoxazol-4-yl]-(3-pyridyl)methanol (B.1.52), 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile (B.1.53), 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)prop-2-ol (B.1.54), 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)prop-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), methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propionic acid (B.1.57);

[0270] -δ14-reductase inhibitors (G2): 4-dodecyl-2,6-dimethylmorpholine (aldimorph) (B.2.1), morpholine (B.2.2), morpholine acetate (B.2.3), butylmorpholine (B.2.4), clindamycin (B.2.5), benzyl sulfadiazine (B.2.6), fenvalerate (B.2.7), spirocyclophosphamide (B.2.8);

[0271] -3-Ketoreductase inhibitors: Cyclopyridamole (B.3.1), Amifenopyram (B.3.2);

[0272] - Other sterol biosynthesis inhibitors: chlorfenapyrazole (B.4.1);

[0273] C) Nucleic acid synthesis inhibitors

[0274] -RNA polymerase I inhibitors (A1): Benalaxyl (C.1.1), Benalaxyl-M (C.1.2), Kiralaxyl (C.1.3), Metalaxyl (C.1.4), Metalaxyl-M (C.1.5), Furazolidone (C.1.6), Oxyxamic acid (C.1.7);

[0275] Other nucleic acid synthesis inhibitors (A2 to A5): oxamyl (C.2.1), octathiazoline (C.2.2), oxaquinic acid (C.2.3), ethirimol sulfonate (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); DHODH inhibitors: isopyram (C.2.9), fluopyram (C.2.10);

[0276] D) Inhibitors of cell division and cytoskeleton

[0277] - Microtubule polymerization inhibitors (MBC, B1): Benomyl (D.1.1), Carbendazim (D.1.2), Mefenoxam (D1.3), Thiophanate-methyl (D.1.4), Methylthiophanate (D.1.5), Pyridachlometyl (D.1.6), N-ethyl-2-[(3-ethynyl-8-methyl-6-quinolinyl)oxy]butyramide (D.1.8), N-ethyl-2-[(3-ethynyl-8-methyl-6-quinolinyl)oxy]-2-methylthioalkyl-acetamide (D.1.9), 2-[(3-ethynyl-8-methyl-6-quinolinyl)oxy]-N-(2-fluoroethyl)butyramide (D.1.10), 2-[(3-ethynyl-8-methyl-6-quinolinyl)oxy]-N-(2- 2-(2-fluoroethyl)-2-methoxy-acetamide (D.1.11), 2-[(3-ethynyl-8-methyl-6-quinolinyl)oxy]-N-propyl-butyramide (D.1.12), 2-[(3-ethynyl-8-methyl-6-quinolinyl)oxy]-2-methoxy-N-propyl-acetamide (D.1.13), 2-[(3-ethynyl-8-methyl-6-quinolinyl)oxy]-2-methylthioalkyl-N-propyl-acetamide (D.1.14), 2-[(3-ethynyl-8-methyl-6-quinolinyl)oxy]-N-(2-fluoroethyl)-2-methylthioalkyl-acetamide (D.1.15), 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazole-3-amine (D.1.16);

[0278] Other cell division inhibitors (B2 to B7): Ethiocarb (D.2.1), Thiamethoxam (D.2.2), Pendimethomorph (D.2.3), Fluopyram (D.2.4), Benzoylamidone (D.2.5), Benomyl (D.2.6), Pyriofenone (D.2.7), Cyazofamid (D.2.8); Fluopyram (D.2.9);

[0279] E) Inhibitors of amino acid and protein synthesis

[0280] - Methionine synthesis inhibitors (D1): Azoxystrobin (E.1.1), Azoxystrobin (E.1.2), Pyrimethanil (E.1.3);

[0281] - Protein synthesis inhibitors (D2 to D5): blastomycin-S (E.2.1), kasugamycin (E.2.2), kasugamycin hydrochloride hydrate (E.2.3), midomycin (E.2.4), streptomycin (E.2.5), oxytetracycline (E.2.6);

[0282] F) Signal transduction inhibitors

[0283] -MAP / histidine kinase inhibitors (E2 and E3): iprodione (F.1.2), procymidone (F.1.3), vinclozolin (F.1.4), fludioxonil (F.1.5);

[0284] -Mechanism unknown (E1): Quinoxaline (F.2.1), Propoxyquin (F.2.2);

[0285] G) Lipid and membrane synthesis inhibitors

[0286] - Phospholipid biosynthesis inhibitors (F2): Kefensan (G.1.1), Isoprothiolane (G.1.2), Dimethoate (G.1.3), Isoprothiolane (G.1.4);

[0287] -Lipid peroxidation (F3): chloronitrobenzene (G.2.1), pentachloronitrobenzene (G.2.2), tetrachloronitrobenzene (G.2.3), methyl thiophanate (G.2.4), biphenyl (G.2.5), dimethoate (G.2.6), chlorpyrifos (G.2.7);

[0288] - Compounds and fatty acids (F4) that affect cell membrane permeability: cymoxanil (G.4.1);

[0289] -Oxidized sterol-binding protein inhibitors (OSBPI, F9): Fluoxapiprolin (G.5.1), Fluoxapiprolin (G.5.3), 4-[1-[2-[3-difluoromethyl-5-methyl-pyrazole-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphthyl-1-yl-pyridin-2-carboxamide (G.5.4), 4-[1-[2-[3,5-bis(difluoromethyl)]acetyl]-4-piperidinyl]-N-tetrahydronaphthyl-1-yl-pyridin-2-carboxamide [Pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphth-1-yl-pyridin-2-carboxamide (G.5.5), 4-[1-[2-[3-(difluoromethyl)-5-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphth-1-yl-pyridin-2-carboxamide (G.5.6), 4-[1-[2-[5-cyclopropyl-3-(difluoromethyl)pyrazol-1-yl]acetyl]-4- [piperidinyl]-N-tetrahydronaphth-1-yl-pyridin-2-carboxamide (G.5.7), 4-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphth-1-yl-pyridin-2-carboxamide (G.5.8), 4-[1-[2-[5-(difluoromethyl)-3-(trifluoromethyl)pyrazol-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphth-1-yl] 4-pyridine-2-carboxamide (G.5.9), 4-[1-[2-[3,5-bis(trifluoromethyl)pyrazole-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphth-1-yl-pyridine-2-carboxamide (G.5.10), (4-[1-[2-[5-cyclopropyl-3-(trifluoromethyl)pyrazole-1-yl]acetyl]-4-piperidinyl]-N-tetrahydronaphth-1-yl-pyridine-2-carboxamide (G.5.11);

[0290] H) Inhibitors with multi-site action

[0291] -Inorganic active substances (MO1, MO2): 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);

[0292] -Thiocarbamates and dithiocarbamates (M03): ferric sulfate (H.2.1), mancozeb (H.2.2), mancozeb (H.2.3), thiamethoxam (H.2.4), mancozeb (H.2.5), methyl mancozeb (H.2.6), thiram (H.2.7), mancozeb (H.2.8), thiram (H.2.9), thiamethoxam zinc (H.2.10);

[0293] - Organochlorine compounds (M04, M05, M06, M08): Dichlorophenoxyacetic acid (H.3.1), Chlorothalonil (H.3.2), Captan (H.3.3), Captan (H.3.4), Captan (H.3.5), Bacteriostatic agent (H.3.6), Dichlorophenol (H.3.7), Hexachlorobenzene (H.3.8), Pentachlorophenol (H.3.9) and its salts, Tetrachlorophthalide (H.3.10), Para-methyl thiophanate (H.3.11);

[0294] -Guinea and others (M07, M09, M10; M11, M12): Guanidine (H.4.1), dextrin (H.4.2), dextrin free base (H.4.3), guazatine (H.4.4), guazatine-acetate (H.4.5), guazatamine (H.4.6), guazatamine triacetate (H.4.7), guazatamine trioctylbenzene sulfonate (H.4.8), dithiazolinone (H.4.9), 2,6-dimethyl-1H,5H-[1,4]dithiacino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetraone (H.4.10), zofuran (H.4.11), sulfadiazine (H.4.12), chlorpyrifos (H.4.13);

[0295] I) Cell wall synthesis inhibitors

[0296] - Dextran synthesis inhibitor: Polyoxin (I.1.1); Chitosan synthase inhibitor (H4): Polyoxin B (I.1.2);

[0297] - Melanin synthesis inhibitors (I1 to I3): Trihydroxynaphthalene reductase inhibitors (MBI-R; I1) cycloquinone (I.2.1), tricyclazole (I.2.2); Dehydratase inhibitors (MBI-D, I2); propiconazole (I.2.3), cyhalofop-p-ethyl (I.2.4), cyazofamid (I.2.5); Polyketide synthase inhibitors (MBI-P, I3): tolprocarb (I.2.6);

[0298] - Cellulose synthase inhibitors (H5): dimethomorph (I.3.1), flumethomorph (I.3.2), dimethomorph (I.3.3), buprofen (I.3.4), bensulfuron-methyl (I.3.5), propineb (I.3.6), valifenalate (I.3.7);

[0299] J) Plant defense inducers (P1 to P8)

[0300] -Aranoic acid benzene-S-methyl (J.1.1), thiabendazole (J.1.2), isothiazine (J.1.3), thiamethoxam (J.1.4), cyclophosphamide-calcium (J.1.5); Phosphonates: ethphosphonic acid (J.1.6), aluminum tris(ethphosphonate) (J.1.7), phosphorous acid and its salts (J.1.8), potassium bicarbonate or sodium bicarbonate (J.1.9), 4-cyclopropyl-N-(2,4-dimethoxyphenyl)thiadiazole-5-carboxamide (J.1.10), calcium phosphonate (J.1.11), potassium phosphonate (J.1.12), dichlorothiazide (J.1.13);

[0301] K) Mode of action unknown (U, unknown)

[0302] - Bronitrofon (K.1.1), Cycloflufenicol (K.1.3), Cymoxanil (K.1.4), Dato'a (K.1.5), Imazalil (K.1.6), Pyridaben (K.1.8), Wild hymexazol (K.1.9), Wild hymexazol-methyl sulfate (K.1.10), Diphenylamine (K.1.11), Seed coating ester (K.1.12), Flumetover (K.1.14), Flumetylsulforim (K.1.60), Sulfocarb (K.1.15), Fluoxadiazon (K.1.16), Hypersensitive protein (K.1.17), Trichloromethylpyridine (K.1.19), Phthalosporin (K.1.2) 0), Quinoline copper (K.1.22), Seboctylamine (K.1.61), Tebufloquin (K.1.24), Leaf phthalide (K.1.25), Azoxystrobin (K.1.26), N'-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methylformamidin (K.1.27), N'-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethyl-phenyl)-N-ethyl-N-methylformamidin (K.1.28), N'-[4-[[3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazol-5-yl] [[oxy]-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidin (K.1.29), N'-(5-bromo-6-indan-2-yloxy-2-methyl-3-pyridyl)-N-ethyl-N-methyl-formamidin (K.1.30), N'-[5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidin (K.1.31), N'-[5-bromo-6-(4-isopropylcyclohexyloxy)-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidin (K.1.32), N'-[5-bromo-2-methyl-6-(1-phenylethoxy)-3-pyridyl]-N -Ethyl-N-methylformamidin (K.1.33), N'-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilyl-propoxy)phenyl)-N-ethyl-N-methylformamidin (K.1.34), N'-(5-difluoromethyl-2-methyl-4-(3-trimethylsilyl-propoxy)phenyl)-N-ethyl-N-methylformamidin (K.1.35), 2-(4-chloro-phenyl)-N-[4-(3,4-dimethoxy-phenyl)-isoxazol-5-yl]-2-prop-2-alkynyloxy-acetamide (K.1.36), 3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidine-3-yl]-pyridine (pyridoxazole) (K.1.37), 3-[5-(4-methylphenyl)-2,3-dimethyl-isoxazolidine-3-yl]-pyridine (K.1.38), 5-chloro-1-(4,6-dimethoxy-pyrimidin-2-yl)-2-methyl-1H-benzimidazole (K.1.39), (Z)-3-amino-2-cyano-3-phenyl-prop-2-enoic acid ethyl ester (K.1.40), tetrazolium pyridine ester (K.1.41), N-[6-[[(Z)-[(1-methyltetrazole-5-yl)-phenyl-methylene] [amino]oxymethyl]-2-pyridyl]amyl carbamate (K. 1.42), N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]but-3-kynyl carbamate (K. 1.43), thiamethoxam (K. 1.48), bromodiphenyl ether (K. 1.49), 2-(6-benzyl-2-pyridyl)quinazoline (K. 1.50), 2-[6-(3-fluoro-4-methoxy-phenyl)-5-methyl- [2-pyridyl]quinazoline (K. 1.51), N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidin (K. 1.53), azoxystrobin (K. 1.54), N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidin (K. 1.56), N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]-N-ethyl -N-methylformamidin (K. 1.57), flufenoxadiazam (K. 1.58), [MoA Recommendation: Class II histone deacetylase inhibitor], 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]cyclopropaneformamide (K. 1.60; WO 2018 / 177894, WO 2020 / 212513), N-((4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl)methyl)propionamide (K.1.62), 3,3,3-trifluoro-N-[[3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide (K.1.63), 3,3,3-trifluoro-N-[[2-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide (K.1.64), N-[2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl]butyramide (K.1.65), N-[[2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-3,3,3-trifluoropropionamide (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]propionamide (K.1.69), N-ethyl 2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide (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]pyrrolidone-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]piperidin-2-one 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]isoxazolidine-3-one (K. 1.75), 2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidine-3-one (K. 1.76), 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidine-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]oxazin-3-one (K. 1.79), 1-[[3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]azacycloheptane-2-one (K. 1.80), 4,4-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidine-2-one (K. 1.81), 5-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidine-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.1.85) 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]propionamide (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]cyclopropaneformamide (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-methyl-phenyl]-N-ethyl-N- Methyl-formamidinium (K. 1.95), N'-[2-chloro-4-[(4-methoxy-phenyl)methyl]-5-methyl-phenyl]-N-ethyl-N-methyl-formamidinium (K. 1.96), N'-[2-chloro-4-[(4-cyano-phenyl)methyl]-5-methyl-phenyl]-N-ethyl-N-methyl-formamidinium (K. 1.97), N'-[2,5-dimethyl-4-(o-tolylmethyl)phenyl]-N-ethyl-N-methyl-formamidinium (K. 1.98), 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide (K. 1.95).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-(3,4-difluoro ... [2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazin-4-carboxamide (K.1.102), 6-chloro-3-(3-chloro-2-fluoro-phenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazin-4-carboxamide (K.1.103), N-[2-(2-bromo-4-methylphenyl)-2,2-difluoroethyl]-6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-5-methylpyridazin-4-carboxamide (K.1.104);

[0303] L) Biological pest control agents

[0304] L1) Microbial agents with antifungal, antibacterial, antiviral, and / or plant defense activator activities: Powdery mildew parasiticus, Aspergillus flavus, Bacillus buddingus, Bacillus hygroscopicus, Bacillus amyloliquefaciens, Bacillus amyloliquefaciens subsp. plantarum (also known as Bacillus bellesii), Bacillus megaterium, Bacillus mohaiweiii, Bacillus mycosis fungiformis, Bacillus pumilus, Bacillus simplex, Bacillus halophyte, Bacillus subtilis, Bacillus amyloliquefaciens var. subtilis, Bacillus bellesii, Candida oligosacchari, Candida saitoana, Clavibactermegia ichiganensis (bacteriophage), Shield mold, Cryptococcus parasiticus, Cryptococcus albus, Dilophosphora alopecuri, Fusarium oxysporum, Clonestachys rosea f. catenulate (also known as Gliocladium) (catenulatum), pink bromoxynil, antibiotic lysinophil, mycolytic bromoxynil, drupocytosaccharomyces, microdochium dimerum, microsporum, Muscodor albus, Bacillus vesicularis, epiphytic Bacillus, polymyxa, pantothecin, Penicillium barometz, *Pseudomonas* species, *Pseudomonas leucosus*, *Pseudozyma flocculosa*, *Pichia aberrant*, *Pythium oligandrum*, *Sphaerodes mycoparasitica*, *Streptomyces glaucum*, *Streptomyces lidiflorus*, *Streptomyces purpureus*, *Trichoderma asperelloides*, *Trichoderma spp.*, *Trichoderma pellucida*, *Trichoderma galbana*, *T. harmatum*, *Trichoderma harzianum*, *T. polysporum*, *T. streptococcus*. stromaticum), Trichoderma virens, Trichoderma viride, Typhula phacorrhiza, Odman's sclerotium, Verticillium dahliae, and small zucchini yellow mosaic virus (non-toxic strain).

[0305] L2) Biochemical pest control agents with antifungal, antibacterial, antiviral and / or plant defense activator activities: hypersensitive protein, Polygonum cuspidatum extract;

[0306] L3) Microbial biocides with insecticidal, acaricidal, snail-killing, and / or nematicidal activity: *Agrobacterium radiata*, *Bacillus cereus*, *Bacillus stolonifer*, *Bacillus thuringiensis*, *Bacillus thuringiensis* subsp. *catella*, *Bacillus thuringiensis* subsp. *israelica*, *Bacillus thuringiensis* subsp. *wax moth*, *Bacillus thuringiensis* subsp. *kulstaq*, *Bacillus thuringiensis* subsp. *tenacylpyridae*, *Beauveria bassiana*, *Beauveria bassiana* species, *Burkholderia* species, and active purple bacteria (Chromobacterium). subtsugae), codling moth granulovirus (CpGV), pseudocodling moth granulovirus (CrleGV), species of Flavobacterium, bollworm nucleopolyhedrovirus (HearNPV), corn noctuid moth nucleopolyhedrovirus (HzNPV), corn noctuid moth monochroic nucleopolyhedrovirus (HzSNPV), *Heterobacter hygrophila*, *Cladosporium flavum*, *Lecanicillium longisporum*, *L. muscarium*, *Metarhizium anisopliae*, *Metarhizium anisopliae* microsporum variant, *Metarhizium anisopliae* locust variant, *Nomura leishii*, *Paecilomyces flavum*, *Paecilomyces lilacinus*, *Bacillus japonicus*, *Bacillus pastoris* species, *Paecilomyces szawa*, *Paecilomyces punctata*, *P. ramosa*, *P. thornea*, *P. ouss*. usgae), fluorescent pseudomonas, gray noctuid moth nucleopolyhedrovirus (SpliNPV), small leafroller nematode, small noctuid moth nematode, sawfly nematode, fresh yellow streptomyces, fine yellow streptomyces;

[0307] L4) Biochemical pest control agents with insecticidal, acaricidal, snail-killing, pheromone-based, and / or nematicidal activities: L-carvone, citral, (E,Z)-7,9-dodecadien-1-yl acetate, ethyl formate, (E,Z)-2,4-decadienoic acid ethyl ester (pear ester), (Z,Z,E)-7,11,13-hexadecanetrienal, heptyl butyrate, isopropyl myristate, lavender ester, cis-jasmone, 2-methyl-1-butanol, methyl eugenol, methyl jasmone, (E,Z)-2,13-octadecadien-1-ol, acetic acid (E,Z) -2,13-octadecadien-1-ol ester, (E,Z)-3,13-octadecadien-1-ol, (R)-1-octen-3-ol, termite pheromone, (E,Z,Z)-3,8,11-tetradecadienyl 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, Quilay extract;

[0308] L5) Microbial pest control agents with plant stress reduction, plant growth regulator, plant growth promotion and / or yield increase activities: Azotobacter agalactiae, Azotobacter brasiliensis, Azotobacter lipophila, Azotobacter iridozoensis, Azotobacter high-salt, Slow-growing rhizobia species, Slow-growing rhizobia ehrlich, Slow-growing rhizobia soybean, Slow-growing rhizobia lizardii, Slow-growing lupin rhizobia, Delfordia acidophila, Arbuscular mycorrhizal fungi, Mesophytic rhizobia species, Rhizobia pea biotype, Rhizobia pea clover biotype, Rhizobia pea broad bean biotype, Rhizobia tropicalis and Rhizobia spp. alfalfa;

[0309] O) Insecticides from categories O.1 to O.29

[0310] 0.1 Acetylcholinesterase (AChE) inhibitors: Aldicarb, fenvalerate, carbofuran, methylcarbate, methylcarbate, carbaryl, carbamate, carbofuran, methylcarbate, ethylcarbate, methylcarbate, imidacloprid, furazolidone, isoprocarb, imidacloprid, methomyl, fenvalerate, chlorpyrifos, propoxur, thiamethoxam, thiophanate-methyl, methylcarbate, XMC, imidacloprid, pymetrozine; Phosphate, methylpyridinium, ethyl phosphonate, phosmet, thiophanate-methyl, phosmet, chlorpyrifos, chlorpyrifos, methyl chlorpyrifos, phosmet, pyridaben, phosmet-S-methyl, diazinon, dichlorvos / DDVP, phosmet, dimethoate, methyl imidacloprid, ethylcarbate Phosphorus, EPN, ethion, propargite, phosmet, benzylphos, fenitrothion, fenthion, thiamethoxam, heptamethrin, cypermethrin, isopropylamine, O-(methoxyaminothio-phosphoryl)salicylic acid isopropyl ester, isoxazolium, malathion, phosmet, methamidophos, chlorpyrifos, phosmet, dibromophos, omethoate, sulfonium phosphate, parathion, methyl parathion, phosmet, phosmet, phosmet, phosmet, phosmet, phosmet, phosmet, phosmet, phosmet, phosmet, phosmet, phosmet, phosmet, phosmet, phosmet, phosmet, phosmet, pyrazophos, pyridazine, quinalphos, phosmet, phosmet, butylpyrimidine, dithion, terbufos, chlorpyrifos, methyl ethion, triazophos, trichlorfon, phosmet.

[0311] O.2 GABA-gated chloride channel antagonists: endosulfan, chlordane; acetamiprid, fipronil, butenpyram, pyrafluprole, pyriprole.

[0312] O.3 Sodium channel modulators: Flufenoxuron, Allethrin, Dextrorotatory-cis-trans Allethrin, Dextrorotatory-trans Allethrin, Bifenthrin, K-Bifenthrin, Bioallethrin, Bioallethrin S-cyclopentenyl, Biobenzylfuran, Cypermethrin, Cypermethrin, β-Cypermethrin, Trifluralin, λ-Cypermethrin, γ-Cypermethrin, Cypermethrin, α-Cypermethrin, β-Cypermethrin, θ-Cypermethrin, ζ-Cypermethrin, Lambda-cypermethrin, Delanolyl, Enyne Pyrethroids, cypermethrin, deltamethrin, cypermethrin, cypermethrin, flufenoxuron, cypermethrin, t-flumethrin, bromoflumethrin, heptamethrin, imidacloprid, chlorflumethrin, methoxyfenozide, methoxyfenozide, ε-methoxyfenozide, permethrin, fenfluroxyfenozide, ethylanthrin, propargite, pyrethroids (pyrethrum), pyrethrum, flusilazole, heptamethrin, κ-heptamethrin, tetrafluoroethylene, pyrethroids, tetrabromopyrethrin, tetrafluoroethylene; DDT, methoxydichlorophenoxyacetic acid (DDT);

[0313] O.4 Nicotinic acetylcholine receptor (nAChR) agonists: acetamiprid, thiamethoxam, cyclopyridamole, dinotefuran, imidacloprid, acetamiprid, thiamethoxam; 4,5-dihydro-N-nitro-1-(2-epoxyethylenemethyl)-1H-imidazol-2-amine, (2E)-1-[(6-chloropyridin-3-yl)methyl]-N'-nitro-2-pentylaminoguanidine; 1-[(6-chloropyridin-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridine; nicotine; flupyridine, flupyrflufenone, trifluralin, dithiazolinone, flupyridine;

[0314] 0.5 Nicotinic acetylcholine receptor allosteric activators: spinosad, ethyl spinosad;

[0315] 0.6 Chloride channel activators: abamectin, emamectin benzoate, ivermectin, rapamycin, mibamectin;

[0316] O.7 Juvenile hormone mimics: acetamiprid, acetamiprid, acetamiprid; phenoxycarb, fenvalerate;

[0317] O.8 Various non-specific (multi-site) inhibitors: methyl bromide and other alkyl halides; trichloronitromethane, sulfonyl fluoride, borax, tartaric acid;

[0318] O.9 Regulators of TRPV channels in string organs: Biprofen, Pymetrozine, Flufenoxuron;

[0319] O.10 Mite growth inhibitors: Tetramethrin, Thiamethoxam, Flumethrin; Etoxazole;

[0320] O.11 Microbial disruptors of the intestinal membrane in insects: Bacillus thuringiensis, Bacillus sphaericus, and their insecticidal proteins: 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;

[0321] O.12 Mitochondrial ATP synthase inhibitors: butyl ether urea; triazole tin, tricyclic tin, phenylbutyl tin, chlorfenapyr, trichlorfon;

[0322] O.13 Oxidative phosphorylation decoupling agents via proton gradient interference: brofentanil, DNOC, fipronil;

[0323] O.14 Nicotinic acetylcholine receptor (nAChR) channel blockers: chlorpyrifos, fenitrothion, chlorpyrifos, dichlorvos;

[0324] O.15 Chitosan biosynthesis inhibitors type 0: bis(triflufenoxuron), flufenoxuron, diflufenoxuron, flucyclourea, flufenoxuron, flufenoxuron, lufenuron, flufenoxuron, polyfluorourea, flubendiamide, chlorfenapyr;

[0325] O.16 Chitosan biosynthesis inhibitor type 1: thiamethoxam;

[0326] O.17 Ecdyskin disruptor: cyromazine;

[0327] O.18 Ecdysone receptor agonists: methoxyfenozide, fenbufenozide, chlorfenapyr, furazolidone, cyclotebufenozide;

[0328] O.19 Octopus amine receptor agonist: Dimethicone;

[0329] O.20 Inhibitors of electron transport in mitochondrial complex III: flufenoxuron, cypermethrin, pyrimethanil, bifenazate;

[0330] O.21 Mitochondrial complex I electron transport inhibitors: quinclorac, azoxystrobin, pyrimethanil, pyridaben, pyridaben, acetamiprid, rotenone;

[0331] O.22 Voltage-dependent sodium channel blockers: indoxacarb, cyfluthrin, 2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylene]-N-[4-(difluoromethoxy)phenyl]-hydrazinoamide, N-(3-chloro-2-methylphenyl)-2-[(4-chlorophenyl)[4-[methyl(methylsulfonyl)amino]phenyl]ethylene]-hydrazinoamide, 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]ethylene]-N-[4-(difluoromethoxy)phenyl]-hydrazinoamide;

[0332] O.23 Acetyl-CoA carboxylase inhibitors: Spirodiclofen, Spirodiclofen, Spirodiclofen, Ethyl methoxypiperidine, Spirodiclofen diester, 11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxa-9-azabispirol[4.2.4.2]tetradecano-11-en-10-one, and spirochete;

[0333] O.24 Mitochondrial complex IV electron transport inhibitors: aluminum phosphide, calcium phosphide, phosphine, zinc phosphide, cyanide;

[0334] 0.25 Mitochondrial complex II electron transport inhibitors: pyridaben, fenflurfen, etoxazole, pyrazolyl aniline;

[0335] 0.28 Rianotinamide receptor modulators: chlorantraniliprole, bromocyanamide, cyclobromocyanamide, flubendiamide, fluchlorfenapyr, (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-pyrazole-5-yl]carbonyl}amino)benzoyl]-1,2-dimethylhydrazine carbamate; N-[4,6-dichloro-2-[(diethyl-λ-4-thionyl)carbamoyl]phenyl]-2-(3-chloro-2-pyridinyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[4-chloro-2-[(diethyl-λ-4-thionyl)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridinyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methyl] [Phenyl]-3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxamide; 3-chloro-1-(3-chloro-2-pyridyl)-N-[2,4-dichloro-6-[[(1-cyano-1-methylethyl)amino]carbonyl]phenyl]-1H-pyrazole-5-carboxamide; tetrachlorfenapyr; tetrazolium fenvalerate; thiofenoxam; N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide; chlorfenapyr; N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridyl)-1H-pyrazole-5-carboxamide;

[0336] O.29 String organ modulator: flupyradifurone;

[0337] 0.30 GABA-gated chloride channel allosteric modulators: brofenoxam, chlorfenapyr, isoxazolidinamide;

[0338] O.33 Calcium-activated potassium channel regulator: Flufenoxuron (acynonapyr);

[0339] O.34 Flumetoquin, a mitochondrial complex III electron transport inhibitor at the Qi site.

[0340] 0.35 Insecticidal compounds with unknown or uncertain modes of action: afurazone, azadirachtin, sulfadiazine, fenpyroxene, bromodiphenyl ether, fenpyroxene, cryolite, cyproflanilid, dichloropyrimipyrimidine, trichlorfon, fenpyrazosulfuron, pyrimethanil, flumetoquin, fluthiamethoxam, fluhexafon, flupyradifon, fleranal, metaldehyde, oxadiazon, synergist ether, acetamiprid, tioxazafen, trifluenfuronate, umifoxolaner, 11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1, 4-Dioxa-9-azabispiro[4.2.4.2]-tetradecano-11-en-10-one, 3-(4'-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4.5]decano-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-benzoyl Amine, 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-methylbenzamide, 1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1H-1,2,4-tetrazol-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-methylbenzamide, 4-cyano-N-[2-cyano-5-[[[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]amino]carbonyl]-2-cyano-phenyl]-4-cyano-2-methylbenzamide, 4-cyano-N-[2-cyano-5-[[[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]amino]carbonyl]-2-cyano-phenyl]-4-cyano-2-methylbenzamide,2-Tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]amino]carbonyl]phenyl]-2-methyl-benzamide, active material based on Bacillus stolonifer (Votivo, I-1582); trifluoroimidazamide; 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-dioxane-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-pyridinyl)-5-thiazolyl]-2-pyridinyl]pyrimidine; N-methylsulfonyl-6-[2-(3-pyridinyl)thiazolyl-5-yl]pyridine-2-carboxamide; N-methylsulfonyl-6-[2-(3-pyridinyl)thiazolyl-5-yl]pyridine-2-carboxamide; 1-[(6-chloro-3-pyridinyl)methyl]-1,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitro-imidazo[1,2-a]pyridine; 1-[(6-chloropyridinyl-3-yl)methyl]-7-methyl-8-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridine-5-ol; N-(3-chloro-2-methylphenyl)-2-[(4-chlorophenyl)[4-[ [Methyl(methylsulfonyl)amino]phenyl]methylene]-hydrazine 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; 2-(3-pyridyl)-N-(2-pyrimidinylmethyl)-2H-indazole-5-carboxamide; chlorpyrifos; saloranar, loteranar; 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-pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide;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; oxazolylsulfadiazine; [(2S,3R,4R,5S,6S)-3,5-dimethoxy-6-methyl-4-propoxy-tetrahydropyran-2-yl]-N-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate; [(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl]N-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate; [(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl]N-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate; [(2S,3 R,4R,5S,6S)-3,5-dimethoxy-6-methyl-4-propoxy-tetrahydropyran-2-yl]-N-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate; [(2S,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyl-tetrahydropyran-2-yl]-N-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate; (2Z)-3-(2-isopropylphenyl)-2-[(E)-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]carbamate [Azol-3-yl]phenyl]methylenehydrazinyl]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]methylenehydrazinyl]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]methylenehydrazinyl]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 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]pyridin-8-carboxynitrile, 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-(trifluoromethyl)imidazo[4,5-b]pyridine 2-[3-ethylsulfonyl-7-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine, 2-(6-bromo-3-ethylsulfonyl-imidazo[1,2-a]pyridin-2-yl)-6-(trifluoromethyl)pyrazolo[4,3-c]pyridine; N-[[2-fluoro-4-[(2S,3S)-2-hydroxy-3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidine-1-yl]phenyl]methyl]cyclopropaneformamide; 2-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfinyl)phenyl]imino-3- (2,2,2-trifluoroethyl)thiazolidin-4-one; flupentixol, N-[3-chloro-1-(3-pyridinyl)pyrazol-4-yl]-2-methylsulfonyl-propionamide, trifluoropyridineamine; N-[4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl]-2-methyl-4-methylsulfonyl-5-(1,1,2,2,2-pentafluoroethyl)pyrazol-3-carboxamide, cyclopropionamide, cyclopropionamide; 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-trifluoroethylthioalkyl)phenyl]imino-3-(2,2,2-Trifluoroethyl)thiazolidin-4-one, indazole, N-[4-chloro-2-(3-pyridyl)thiazolidin-5-yl]-N-ethyl-3-methylsulfonyl-propionamide, N-cyclopropyl-5-[(5S)-5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isooxazol-3-yl]isoquinoline-8-carboxamide, 5-[(5S)-5-(3,5-dichloro-4-fluoro-phenyl)-5-(trifluoromethyl)-4H-isooxazol-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-carbamate)-2-chloro-N-(3-(2,2-difluoroacetamido)-2,4-difluorophenyl)benzamide, 1-[6-(2,2-difluoro-7-methyl-[1,3]dioxane[4,5-f]benzimidazole-6-yl)-5-ethylsulfonyl-3-pyridyl]cyclopropanecarboxynitrile, 6-(5-cyclopropyl-3-ethylsulfonyl-2-pyridyl)-2,2-difluoro-7-methyl-[1,3]dioxane[4,5-f]benzimidazole.

[0341] The active substance referred to as component 2, its preparation, and its activity, for example, against harmful fungi, are known (see: https: / / pesticidecompendium.bcpc.org / ); these substances are commercially available. Compounds described by IUPAC nomenclature, their preparation, and their phytotoxic activities are also known (see Can.J. Plant Sci. 48(6), 587-94, 1968; EP-A 141 317; EP-A 152 031; EP-A 226 917; EP-A 243970; EP-A 256 503; EP-A 428 941; EP-A 532 022; EP-A 1 028 125; EP-A 1 035 122; EP-A1 201 648; EP-A 1 122 244, JP 2002316902; DE 19650197; DE 10021412; DE102005009458; US 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, CN1907024, CN 1456054, CN 103387541, CN 1309897, WO 12 / 84812, CN 1907024,WO09094442,WO WO 14 / 60177, WO 13 / 116251, WO 08 / 013622, WO 15 / 65922, WO 94 / 01546, EP2865265, WO 07 / 129454, WO 12 / 165511, WO 11 / 081174, WO 13 / 47441, WO 16 / 156241, WO16 / 162265). Some compounds are identified by their CAS registry number, which is divided into three parts by hyphens: the first part consists of two to seven digits, the second part consists of two digits, and the third part consists of a single digit.

[0342] According to the present invention, the solid material (dry matter) of biocidal agents (excluding oils such as neem oil) is considered the active component (e.g., obtained after drying or evaporation extraction or suspension in the case of liquid formulations of microbial agents). The weight ratios and percentages used for biological extracts such as soap extracts are based on the total weight of the dry content (solid material) of one or more of the respective extracts.

[0343] 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 component using the following equation: 1 × 10⁻⁶ 10 CFU equals the total weight of one gram of the corresponding active ingredient. Colony forming unit is a measure of living microbial cells. Furthermore, in the case of nematode biocides such as Steinernema feltiae, "CFU" can also be understood as the number of (juvenile) individual nematodes.

[0344] In binary mixtures, the weight ratio of component 1) to component 2) generally depends on the properties of the components used, typically 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 particularly in the range of 1:2 to 2:1. According to another embodiment, the weight ratio of component 1) to component 2) is generally from 1000:1 to 1:1, often from 100:1 to 1:1, frequently from 50:1 to 1:1, preferably from 20:1 to 1:1, more preferably from 10:1 to 1:1, even more preferably from 4:1 to 1:1, and particularly in the range of 2:1 to 1:1. According to another embodiment, the weight ratio of component 1) to component 2) is typically from 20,000:1 to 1:10, often from 10,000:1 to 1:1, frequently from 5,000:1 to 5:1, preferably from 5,000:1 to 10:1, more preferably from 2,000:1 to 30:1, even more preferably from 2,000:1 to 100:1, and particularly in the range of 1,000:1 to 100:1. According to another embodiment, the weight ratio of component 1) to component 2) is typically from 1:1 to 1:1000, often from 1:1 to 1:100, frequently from 1:1 to 1:50, preferably from 1:1 to 1:20, more preferably from 1:1 to 1:10, even more preferably from 1:1 to 1:4, and particularly in the range of 1:1 to 1:2. According to another embodiment, the weight ratio of component 1) to component 2) is typically from 10:1 to 1:20,000, often from 1:1 to 1:10,000, frequently from 1:5 to 1:5,000, preferably from 1:10 to 1:5,000, more preferably from 1:30 to 1:2,000, even more preferably from 1:100 to 1:2,000, and particularly in the range of 1:100 to 1:1,000.

[0345] In a ternary mixture, i.e., a composition comprising component 1), component 2), and compound III (component 3), the weight ratio of component 1) to component 2) depends on the characteristics of the active substance used, and is typically in the range of 1:100 to 100:1, often 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 particularly in the range of 1:4 to 4:1, and the weight ratio of component 1) to component 3) is typically in the range of 1:100 to 100:1, often 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 particularly in the range of 1:4 to 4:1. If necessary, any additional active ingredients may be added to component 1) at a ratio of 20:1 to 1:20. These ratios are also suitable for mixtures applied via seed treatment.

[0346] When mixtures containing microbial pesticides are used for crop protection, the application rate range is 1 × 10⁻⁶. 6 Up to 5 × 10 16 (or greater) CFU / ha, preferably 1 × 10 8 Up to 1 × 10 13 CFU / ha, and even more preferably 1 × 10 9 Up to 5 × 10 15 CFU / ha, and especially 1 × 10 12 Up to 5 × 10 14 CFU / ha. When nematodes are used as microbial pest control agents (e.g., *Nocturia stearothermia*), the application rate often ranges from 1 × 10⁻⁶. 5 Up to 1 × 10 12 (or larger), preferably 1 × 10 8 Up to 1 × 10 11 More preferably 5 × 10 8 Up to 1 × 10 10 Individual (e.g., in the form of egg, larva or any other living stage, preferably in the infetive larval stage) / ha.

[0347] When mixtures containing microbial pesticides are used for seed treatment, the application rate typically ranges from 1 × 10⁻⁶. 6 Up to 1 × 10 12 (or larger) CFU / seed, preferably 1 × 10 6 Up to 1 × 10 9 CFU / seed. Furthermore, the application rate for seed treatment is typically in the range of 1 × 10⁻⁶. 7Up to 1 × 10 14 (or larger) CFU / 100 kg seeds, preferably 1 × 10 9 Up to 1× 10 12 CFU / 100 kg of seeds.

[0348] Preferably, it is a mixture comprising at least one active substance as component 2), wherein the at least one active substance is selected from group A) in Q. o The site-specific complex III inhibitor is 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).

[0349] Also preferred is a mixture comprising at least one active substance as component 2), wherein the at least one active substance is selected from group A) in Q. i The site-specific complex III inhibitor is 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).

[0350] Also preferred is a mixture comprising at least one active substance as component 2), wherein the at least one active substance is selected from complex II inhibitors of group A), and more preferably 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), and (A.3.38). and (A.3.39); in particular 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).

[0351] Also preferred is a mixture comprising at least one active substance as component 2), the at least one active substance being selected from other respiratory inhibitors and QoSIs of group A), more preferably selected from compounds (A.4.5) and (A.5.1); especially (A.5.1).

[0352] Also preferred is a mixture comprising at least one active substance as component 2), wherein the at least one active substance is selected from C14 demethylase inhibitors of component B), and more preferably 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.1.33), (B.1.34), (B.1.37), (B.1.38), (B.1.43), (B.1.46), (B.1.53), and (B.1.54). and (B.1.55); particularly selected from (B.1.5), (B.1.8), (B.1.10), (B.1.17), (B.1.22), (B.1.23), (B.1.25), (B.1.33), (B.1.34), (B.1.37), (B.1.38), (B.1.43) and (B.1.46).

[0353] Also preferred is a mixture comprising at least one active substance as component 2), the at least one active substance being selected from δ14-reductase inhibitors of component B), more preferably selected from compounds (B.2.4), (B.2.5), (B.2.6) and (B.2.8); especially (B.2.4).

[0354] It is also preferred to include a mixture comprising at least one active substance as component 2), wherein the at least one active substance is selected from phenylamide and acyl amino acid fungicides of group C), more preferably selected from compounds (C.1.1), (C.1.2), (C.1.4) and (C.1.5); particularly selected from (C.1.1) and (C.1.4).

[0355] It is also preferred to include a mixture comprising at least one active substance as component 2), the 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), (C.2.8), (C.2.9) and (C.2.10); especially (C.2.9) and (C.2.10).

[0356] It is also preferred to include a mixture comprising at least one active substance as component 2), the at least one active substance being selected from group D), more preferably 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).

[0357] It is also preferred to include a mixture comprising at least one active substance as component 2), the at least one active substance being selected from group E), more preferably from compounds (E.1.1), (E.1.3), (E.2.2) and (E.2.3); especially (E.1.3).

[0358] It is also preferred to include a mixture comprising at least one active substance as component 2), wherein the at least one active substance is selected from group F), more preferably from compounds (F.1.2), (F.1.4) and (F.1.5).

[0359] Also preferred is a mixture comprising at least one active substance as component 2), the at least one active substance being selected from group G), more preferably from compounds (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.5.1) and (G.5.3).

[0360] Also preferred is a mixture comprising at least one active substance as component 2), the at least one active substance being selected from group H), more preferably 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).

[0361] It is also preferred to include a mixture comprising at least one active substance as component 2), the at least one active substance being selected from group I), more preferably from compounds (I.2.2), (I.2.5), (I.3.1), (I.3.3) and (I.3.6); especially (I.3.1).

[0362] It is also preferred to include a mixture comprising at least one active substance as component 2), the at least one active substance being selected from group J), more preferably from compounds (J.1.2), (J.1.5), (J.1.8), (J.1.11) and (J.1.12); especially (J.1.5).

[0363] It is also preferred to include a mixture comprising at least one active substance as component 2), wherein the at least one active substance is selected from component K), more preferably from compounds (K.1.41), (K.1.42), (K.1.57), (K.1.58) and (K.1.59); particularly selected from (K.1.41), (K.1.57), (K.1.58) and (K.1.59).

[0364] Biopesticides from groups L1) and / or L2) may also possess insecticidal, acaricidal, molluscicidal, pheromone-based, nematicidal, plant stress-reducing, plant growth-regulating, plant growth-promoting, and / or yield-enhancing activities. Biopesticides from groups L3) and / or L4) may also possess fungicidal, bactericidal, virucidal, plant defense activator, plant stress-reducing, plant growth-regulating, plant growth-promoting, and / or yield-enhancing activities. Biopesticides from group L5) may also possess fungicidal, bactericidal, virucidal, plant defense activator, insecticidal, acaricidal, molluscicidal, pheromone-based, and / or nematicidal activities.

[0365] Microbial agents that kill pests, particularly those from groups L1), L3), and L5), include not only pure cultures of the corresponding microorganisms as defined herein, but also cell-free extracts thereof, suspensions thereof in whole broth cultures and metabolite-containing media, or purified metabolites obtained from whole broth cultures of microorganisms.

[0366] Many of these biocides are deposited using the accession numbers mentioned in this article (prefixes such as ATCC or DSM refer to the acronyms for the corresponding culture deposits; see here for details, for example: http: / / www. wfcc.info / ccinfo / collection / by_acronym / The following strains are mentioned in the literature, registered and / or commercially available: a mixture of *Brucea buddinga* DSM14940 and DSM 14941 isolated in Constance, Germany in 1989 (e.g., budding spores, from bio-ferm GmbH, Austria, BlossomProtect®); *Azotoxinus brasiliensis* Sp245 originally isolated in the wheat region of southern Brazil (Pazufontu) at least before 1980 (BR 11005; e.g., from BASF Agricultural Specialties Ltd., Brazil, GELFIX® Gramíneas); *Azotoxinus brasiliensis* strains Ab-V5 and Ab-V6 (e.g., from Novozymes BioAg Produtos papra Agricultura Ltda., Quattro Barras, Brazil). AzoMax from Brazil or Simbiose-Maíz® from Simbiose-Agro, Brazil; Plant Soil 331, 413-425, 2010), Bacillus amyloliquefaciens strain AP-188 (NRRL B-50615 and B-50331; US ​​8,445,255); Bacillus amyloliquefaciens subsp. plantarum strain, formerly sometimes referred to as Bacillus subtilis, recently classified as Bacillus berleisei along with B. methylotrophicus and Bacillus berleisei (Int. J. Syst. Evol. Microbiol. [International Journal of Systematic and Evolutionary Microbiology] 66, 1212-1217, 2016): Bacillus amyloliquefaciens subsp. plantarum or Bacillus berleisei D747 (US 20130236522) isolated from the air in Kikukawa City, Japan. A1; FERM BP-8234; e.g., Double Nickel™ 55 WDG from Certis LLC, USA), *Bacillus amyloliquefaciens* subsp. *plantae* or *Bacillus belyes* FZB24 (also known as SB3615; DSM 96-2; J. Plant Dis. Prot. [Journal of Plant Diseases and Control] 105, 181-197, 1998; e.g., Taegro® from Novozyme Biologicals, Inc., USA), *Bacillus amyloliquefaciens* subsp. *plantae* or *Bacillus belyes* FZB42 (DSM 23117; J. Plant Dis. Prot.) isolated from soil in Brandenburg, Germany.[Journal of Plant Diseases and Control] 105, 181-197, 1998; e.g., RhizoVital® 42 from AbiTEP GmbH, Germany), *Bacillus plantarum* subsp. *amylloides* or *Bacillus belysium* MBI600 (also known as 1430; NRRL B-50595; US 2012 / 0149571 A1; e.g., Integral® from BASF Corp., USA), *Bacillus plantarum* subsp. *amylloides* or *Bacillus belysium* QST-713 (NRRL B-21661; e.g., Serenade® MAX from Bayer Crop Science LP, USA), *Bacillus plantarum* or *Bacillus belysium* QST-713 (NRRL B-21661; e.g., Serenade® MAX from Bayer Crop Science LP, USA), *Bacillus plantarum*, *Bacillus belysium ... *Bacillus amyloliquefaciens* subsp. *plantae* or *Bacillus belesii* TJ1000 (also known as 1BE; ATCC BAA-390; CA 2471555 A1; e.g., QuickRoots™ from TJ Technologies, Watertown, SD, USA, USA); *Bacillus sturdier* CNCM I-1582, a variant of parent strain EIP-N1 isolated from soil in the Central Plains of Israel (CNCM I-1556) (WO 2009 / 126473, US 6,406,690; e.g., Votivo® from Bayer Crop Science, LLC, USA); *Bacillus pumilus* GHA180 isolated from the rhizosphere of apple trees in Mexico (IDAC 260707-01; e.g., PRO-MIX® from Premier Horticulture, Quebec, Canada, Canada). B. pumilus INR-7, also known as BU-F22 and BU-F33, was isolated from cucumbers infected with Erwinia tracheiphila (NRRL B-50185, NRRL B-50153; US 8,445,255) at least before 1993. B. pumilus KFP9F was isolated from the rhizosphere of grasses in South Africa at least before 2008 (NRRL B-50754; WO 2014 / 029697; for example, from BASF Agricultural Specialities (Pty) Ltd., South Africa).Bac-UP or FUSION-P from South Africa), Bacillus pumilus QST 2808 was isolated in 1998 from soil collected in Pohnpei, Federated States of Micronesia (NRRL B-30087; e.g., Sonata® or Ballad® Plus from Bayer Crop Science LLC), Bacillus simplex ABU 288 (NRRL B-50304; US 8,445,255), also known as UD 1022 or UD10-22, and Bacillus subtilis FB17 were isolated from red beet roots in North America (ATCC PTA-11857; System. Appl. Microbiol. [Systems and Applied Microbiology] 27, 372-379, 2004; US 2010 / 0260735; WO 2011 / 109395); Bacillus thuringiensis subsp. tsuriae ABTS-1857 was isolated in 1987 from soil taken from Ephraim lawns in Wisconsin, USA (also known as ABG-6346; ATCC SD-1372; e.g., XenTari® from BioFa AG, Münsingen, Germany); Bacillus thuringiensis subsp. kurstak ABTS-351 is equivalent to HD-1 isolated in 1967 from diseased bollworm larvae in Brownsville, Texas, USA (ATCC SD-1275; e.g., Dipel® DF from Valent BioSciences, IL, USA); Bacillus thuringiensis subsp. kurstak SB4 was isolated from the cadavers of African stem borer (E. saccharina) larvae (NRRL). B-50753; e.g., Beta Pro® from BASF Agriproducts Ltd., South Africa), Bacillus thuringiensis subsp. *Bacillus* NB-176-1, a mutant of strain NB-125, a wild-type strain isolated in 1982 from the dead pupae of the mealworm (DSM 5480; EP 585 215 B1; e.g., Novodor® from ValentBioSciences, Switzerland), Beauveria bassiana GHA (ATCC 74250; e.g., BotaniGard® 22WGP from Laverlam Int. Corp., USA), Beauveria bassiana JW-1 (ATCC 74040; e.g., CBC (Europe) Srl.Naturalis® (Italy), Beauveria bassiana PPRI 5339 was isolated from the larvae of the tortoise beetle Conchyloctenia punctata (NRRL 50757; e.g. BroadBand® from BASF Agricultural Specialties Ltd., South Africa), SEMIA 5019 (also known as 29W) strain of SEMIA 587 was isolated in Rio de Janeiro, Brazil and in 1967 in the State of Rio Grande do Sul, from areas previously inoculated with North American isolates and used as commercial inoculum since 1968 (Appl. Environ. Microbiol. [Applied and Environmental Microbiology] 73(8), 2635, 2007; e.g. GELFIX 5 from BASF Agricultural Specialties Ltd., Brazil), and Soybean Slow Rhizobium 532c was isolated from a field in Wisconsin, USA (Nitragin 61A152; Can. J.). Plant. Sci. [Canadian Journal of Plant Science] 70, 661-666, 1990; e.g., Rhizoflo®, Histick®, Hicoat® Super from BASF Agricultural Specialties Ltd., Canada), strain USDA 138 of soybean slow-growing rhizobium E-109 variant (INTA E109, SEMIA 5085; Eur. J. Soil Biol. [European Journal of Soil Biology] 45, 28-35, 2009; Biol. Fertil. Soils [Soil Biology and Fertility] 47, 81-89, 2011); by Appl. Environ. Microbiol.[Applied and Environmental Microbiology] 73(8), 2635, 2007 Known soybean slow-growing rhizobium strains preserved in SEMIA: SEMIA 5079 was isolated from soil by the Brazilian Institute of Agricultural Research in Cerrados (Embrapa-Cerrados) in the Cerrados region of Brazil and has been used as a commercial inoculum since 1992 (CPAC 15; e.g., GELFIX 5 or ADHERE 60 from BASF Agroproducts, Brazil); SEMIA 5080, a soybean slow-growing rhizobium obtained in laboratory conditions by Embrapa-Cerrados in Brazil and has been used as a commercial inoculum since 1992, is a natural variant of SEMIA 586 originally isolated in the United States (CB1809) (CPAC 7; e.g., GELFIX 5 or ADHERE 60 from BASF Agroproducts, Brazil); Burkholderia species A396 was isolated from soil in Nikko, Japan in 2008 (NRRL). B-50319; WO 2013 / 032693; Marrone Bio Innovations, Inc., USA), *Scutellaria baicalensis* CON / M / 91-08 isolated from rapeseed (WO 1996 / 021358; DSM 9660; e.g., Contans® WG, Intercept® WG from Bayer CropScience AG, Germany), hypersensitive protein (α-β) (Science 257, 85-88, 1992; e.g., Messenger™ or HARP-N-Tek from PlantHealth Care plc, UK), HearNPV (J. Invertebrate Pathol. 107, 112-126, 2011; e.g., from Adermatt Biocontrol, Switzerland). Helicovex® from Biocontrol, Switzerland; Diplomata® from Koppert, Brazil; and AgBiTech Pty Ltd from Queensland, Australia.Vivus® Max from Queensland, Australia), corn noctuid moth monocotyledon nucleopolyhedrovirus (HzSNPV) (e.g., Gemstar® from Cernan LLC, USA), corn noctuid moth nucleopolyhedrovirus ABA-NPV-U (e.g., Heligen® from AgroBiotech Ltd, Queensland, Australia), Hemibarbus hygrophilus (e.g., Nemasys® G from BASF Agricultural Specialities Limited, UK), Apopka-97 of *Metasequoia glyptostroboides* isolated from mealybugs on *Apis purpurea* in Apopka, Florida, USA (ATCC 20874; Biocontrol Science Technol. [Biological Control Science and Technology] 22(7), 747-761, 2012; e.g., PFR-97™ or PreFeRal® from Cernan LLC, USA), also known as 275 or V275, *Metarhizium anisopliae* microsporum variant F52 isolated from codling moth in Austria (DSM) 3884, ATCC90448; e.g., Met52®, Novozymes BiologicalsBioAg Group, Canada); *Megasteria burmannii* 277 isolated from grapes in central Israel (US 6,994,849; NRRL Y-30752; e.g., previously from Agrogreen Israel's Shemer®); *Paecilomyces lilacinus* 251 isolated from infected nematode eggs in the Philippines (AGAL 89 / 030550; WO 1991 / 02051; Crop Protection 27, 352-361, 2008; e.g., from Bayer Crop Science AG's BioAct® and from CeraCon®, USA); *Bacillus nasus* NAS6G6 isolated from grass rhizosphere in South Africa at least before 2008 (WO2014 / 029697; NRRL). B-50755; for example, from BASF Agricultural Specialities (Pty) Ltd., South Africa.Bacillus strains isolated from soil samples from various European regions, including Germany (BAC-UP): Epiphytic Bacillus Lu17015 (WO 2016 / 020371; DSM 26971), Polymyxin Bacillus plantarum Lu16774 (WO 2016 / 020371; DSM 26969), Polymyxin Bacillus plantarum strain Lu17007 (WO2016 / 020371; DSM 26970); Pasteurella multocida Pn1 was isolated from a soybean field in Illinois, USA in the mid-2000s (ATCC SD-5833; Federal Register [Federal Register] 76(22), 5808, February 2, 2011; Clariva™ PN from Syngenta Crop Protection, LLC, for example, Penicillium baicalensis (also known as P. baicalensis). The strains *Bilaii* ATCC 18309 (= ATCC 74319), ATCC 20851, and / or ATCC22348 (= ATCC 74318) were originally isolated from soil in Alberta, Canada (Fertilizer Research, 39, 97-103, 1994; Can.J. Plant Sci., 78(1), 91-102, 1998; US 5,026,417, WO 1995 / 017806; e.g. Jump Start®, Provide® from Novozymes BioAgriculture Group, Canada), Polygonum cuspidatum extract (EP 0307510 B1; e.g. Regalia® from Marrone BioInnovations, Davis, CA, USA). Milsana® (SC or from Bayer AG, Germany), Small leafroller nematode (e.g., Millenium® from BASF Agriproducts Ltd., UK), and Noctuida spp. nematode (e.g., from BioWorks, Inc., USA).Nemashield® (from BASF Agriproducts Ltd., USA); Nemasys® (from BASF Agriproducts Ltd., UK); *Streptomyces flavus* NRRL B-50550 (WO 2014 / 124369; Bayer Crop Science, Germany); *Trichoderma hygroscopicum* JM41R isolated in South Africa (NRRL 50759; also known as *Trichoderma apicals*; e.g., Trichoplus® from BASF Agriproducts Ltd., South Africa); *Trichoderma harzianum* T-22 also known as KRL-AG2 (ATCC 20847; BioControl [Biological Control] 57, 687-696, 2012; e.g., Plantshield® from American Bioengineering Company or SabrEx™ from Advanced Biological Marketing Inc., VanWert, OH, USA).

[0367] According to another embodiment of the mixture, at least one biocidal agent II is selected from groups L1 to L5:

[0368] L1) Microbial agents with antifungal, antibacterial, antiviral, and / or plant defense activator activities: *Bacillus buddingus* DSM 14940 and DSM 14941 (L1.1), *Bacillus amyloliquefaciens* AP-188 (L1.2), *Bacillus amyloliquefaciens* subsp. *plantarea* D747 (L1.3), *Bacillus amyloliquefaciens* subsp. *plantarea* FZB24 (L1.4), *Bacillus amyloliquefaciens* subsp. *plantarea* FZB42 (L1.5), *Bacillus amyloliquefaciens* subsp. *plantarea* MBI600 (L1.6), *Bacillus amyloliquefaciens* subsp. *plantarea* QST-713 (L1.7), *Bacillus amyloliquefaciens* subsp. *plantarea* TJ1000 (L1.8), *Bacillus pumilus* GB34 (L1.9), *Bacillus pumilus* GHA 180 (L1.10), *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), *Scutellaria baicalensis* CON / M / 91-08 (L.1.16), *Saccharomyces cerevisiae* NRRL Y-30752 (L.1.17), *Bacillus vesicularis* NAS6G6 (L.1.18), *Bacillus epiphyticus* Lu17015 (L.1.25), *Bacillus polymyxa* subsp. *plantare* Lu16774 (L.1.26), *Bacillus polymyxa* subsp. *plantare* strain Lu17007 (L.1.27), *Penicillium baicalensis* ATCC 22348 (L.1.19), *Penicillium baicalensis* ATCC 20851 (L.1.20), Penicillium baicalensis ATCC 18309 (L.1.21), Streptomyces flavus NRRL B-50550 (L.1.22), Trichoderma hydathodes JM41R (L.1.23), Trichoderma harzianum T-22 (L.1.24);

[0369] L2) Biochemical pesticides with fungicidal, bactericidal, virucidal and / or plant defense activator activities: hypersensitive protein (L.2.1), Polygonum cuspidatum extract (L.2.2);

[0370] L3) Microbial biocides with insecticidal, acaricidal, snailicidal, and / or nematicidal activities: Bacillus thuringiensis I-1582 (L.3.1); Bacillus thuringiensis subsp. niger ABTS-1857 (L.3.2), Bacillus thuringiensis subsp. Kurstak ABTS-351 (L.3.3), Bacillus thuringiensis subsp. Kurstak SB4 (L.3.4), Bacillus thuringiensis subsp. *Bacillus thuringiensis* 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), HearNPV (cotton bollworm nucleopolyhedrovirus) (L.3.10), HzNPV ABA-NPV-U (corn noctuid moth nucleopolyhedrovirus) (L.3.11), HzSNPV (corn noctuid moth monocotyledon nucleopolyhedrovirus) (L.3.12), Heterohabditis bacteriophora (L.3.13), Apopka-97 (L.3.14), Microsporum variegatum F52 (scarlet beetle), Paecilomyces lilacinus 251 (L.3.16), Pasteurella multocida Pn1 (L.3.17), Small leafroller nematode (L.3.18), Small noctuid moth nematode (L.3.19);

[0371] L4) Biochemical pest control agents with insecticidal, acaricidal, snailic, pheromone-based and / or nematicidal activities: cis-jasmone (L.4.1), methyl jasmone (L.4.2), and soap extract (L.4.3);

[0372] L5) Microbial pest control agents with plant stress reduction, plant growth regulator, plant growth promotion and / or yield enhancement activities: *Azotobacter brasiliensis* Ab-V5 and Ab-V6 (L.5.1), *Azotobacter brasiliensis* Sp245 (L.5.2), *S. japonicum* SEMIA 587 (L.5.3), *S. japonicum* SEMIA 5019 (L.5.4), *B. japonicum* 532c (L.5.5), *B. japonicum* E-109 (L.5.6), *B. japonicum* SEMIA5079 (L.5.7), *B. japonicum* SEMIA 5080 (L.5.8).

[0373] Furthermore, the present invention relates to agricultural chemical compositions comprising a mixture of at least one compound I (component 1) and at least one biocide selected from group L) (component 2), particularly at least one biocide selected from groups L1) and L2) as described above, and (if necessary) at least one suitable adjuvant.

[0374] Furthermore, the present invention relates to agricultural chemical compositions comprising a mixture of at least one compound I (component 1) and at least one biocide selected from group L) (component 2), particularly at least one biocide selected from groups L3) and L4) as described above, and (if necessary) at least one suitable adjuvant.

[0375] Also preferred is a mixture comprising a biocide as biocide II (component 2), the biocide being selected from groups L1), L3), and L5), preferably selected from those indicated 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), and (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) The strains are 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 propagating 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 legumes such as soybeans.

[0376] Also preferred is a mixture comprising a biocide as biocide II (component 2), the biocide being selected from groups L1 and L3. And L5), preferably selected from (L1.1), (L.1.2), (L.1.3), (L.1.6), (L.1.7), (L.1.9), (L.1.11), (L.1.12), (L.1.13), (L.1.14), (L.1.15), (L.1.17), (L.1.18), (L.1.22), (L.1.23), (L.1.24), (L.1.25), (L.1.26), (L.1.27), (L.2.2); (L.3.2), (L.3.3), (L.3.4), (L.3.5), (L.3.6), (L.3.7), (L.3... (L.3.10), (L.3.11), (L.3.12), (L.3.13), (L.3.14), (L.3.15), (L.3.18), (L.3.19); (L.4.2) strains, even more preferably selected from (L.1.2), (L.1.7), (L.1.11), (L.1.13), (L.1.14), (L.1.15), (L.1.18), (L.1.23), (L.3.3), (L.3.4), (L.3.6), (L.3.7), (L.3.8), (L.3.10), (L.3.11), (L.3.12), (L.3.15) and (L.4.2). These mixtures are particularly suitable for foliar treatment of cultivated plants, especially vegetables, fruits, vines, grains, corn, and legumes such as soybeans.

[0377] Compositions containing mixtures of active ingredients can be prepared by common means, such as those given for compositions of compound I.

[0378] When live microorganisms, such as those from groups L1), L3), and L5), form part of a biocidal agent II, such compositions can be prepared by common means (e.g., HD Burges: Formulation of Microbial Biopesticides, Springer, 1998; WO2008 / 002371, US 6,955,912, US 5,422,107).

[0379] Synthesis Example

[0380] Example 1: Preparation of 5-(8-fluoro-2,2-dimethyl-1,3-benzoxazin-4-yl)-3-methyl-pyridine-2-carboxylonitrile

[0381] 1. Preparation of (8-fluoro-2,2-dimethyl-1,3-benzoxazin-4-yl)trifluoromethanesulfonate

[0382]

[0383] Trifluoromethanesulfonic anhydride (16.69 g, 1.6 equivalents) and 2,6-dimethylpyridine (6.34 g, 1.6 equivalents) were added dropwise to a suspension of 8-fluoro-2,2-dimethyl-3H-1,3-benzoxazin-4-one (for synthesis, see JP2011148714 and WO 2009119089 A1); 7.0 g, 1 equivalent) in dichloromethane (70 mL), and the mixture was stirred at the same temperature for 1.0 h. The reaction mixture was stirred at 0°C for 20 min, poured into ice water, and the solution was extracted with dichloromethane. The organic layer was washed successively with saturated aqueous sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate, and concentrated under vacuum to give the title compound (7.1 g) as a brown oil. The title compound was used directly without further purification.

[0384] Preparation of 2,5-(8-fluoro-2,2-dimethyl-1,3-benzoxazin-4-yl)-3-methylpyridin-2-carboxylonitrile

[0385]

[0386] (6-cyano-5-methyl-3-pyridyl)boronic acid (233 mg, 1.44 equivalents), potassium carbonate (0.99 g, 5 equivalents), water (3 mL), and dichlorobis(triphenylphosphine)palladium(II) (101 mg, 0.14 equivalents) were added to a solution of trifluoromethanesulfonic acid (8-fluoro-2,2-dimethyl-1,3-benzoxazin-4-yl) ester (470 mg, 1.44 equivalents) in dimethoxyethane (15 mL), and the mixture was stirred at 80°C for 12 hours under an argon atmosphere. After cooling, the reaction solution was diluted with ethyl acetate, washed successively with water and brine, dried over anhydrous magnesium sulfate, and concentrated under vacuum. The crude product was purified by silica gel high-performance liquid chromatography (HPLC-column Kinetex XB C18 1,7µ (50 × 2,1 mm); eluent: acetonitrile / water (gradient from 5:95 to 100:0 over 1.5 min at 60°C, flow rate gradient from 0.8 to 1.0 ml / min over 1.5 min)) to give the title compound as a yellow-brown viscous oil.

[0387] 1H NMR (400 MHz, CDCl3): δ [ppm] = 8.71 (d, J = 2.0 Hz, 1H), 7.90 (d,J = 2.0 Hz, 1H), 7.29 - 7.21 (m, 1H), 6.89 (qd, J = 7.7, 3.2 Hz, 2H), 2.64 (s, 3H), 1.72 (s, 6H).

[0388] Table I: Compounds Ex-1 to Ex-3 having Formula I, wherein R 1 and X 2 The meaning is as defined in each line.

[0389]

[0390] LCMS: Liquid Chromatography-Mass Spectrometry; Shimadzu Nexera LC-30 LCMS-2020 (ESI+), using HPLC-Kinetex XB C18 column 1.7µ (50 × 2.1 mm); eluent: acetonitrile / water + 0.1% trifluoroacetic acid (gradient from 5:95 to 100:0 over 1.5 min at 60°C, flow rate gradient from 0.8 to 1.0 mL / min over 1.5 min);

[0391] LCMS: Liquid Chromatography-Mass Spectrometry; Shimadzu Nexera LC-30 LCMS-2020 (ESI+), using HPLC column LUX Cellulose-1 5 µm (150 × 4.6 mm); eluent: acetonitrile / water + 0.1% formic acid (gradient from 50:50 to 100:0 over 10 min at 40°C, flow rate 0.6 mL / min);

[0392] RT: Retention time in minutes.

[0393]

[0394] microtest

[0395] The active compound was prepared separately as a stock solution with a concentration of 10,000 ppm in dimethyl sulfoxide.

[0396] Example 1 - Activity against Botrytis cinerea (gray mold) in microtiter plate test

[0397] Mix the stock solution according to the specified ratio, transfer it to a microtiter plate (MTP) using a pipette, and dilute with water to the specified concentration. Then add a spore suspension of *Botrytis cinerea* in bio-malt or yeast-bacterial peptone-sodium acetate aqueous solution. Place these plates in a water vapor saturated chamber at 18°C. Measure the MTP at 405 nm using an absorbance spectrophotometer 7 days after inoculation.

[0398] In this test, samples treated with 31 ppm of active substance from Examples Ex-1, Ex-2, Ex-3, and Ex-4 showed a pathogen growth rate of up to 13%.

[0399] Example 2 - Activity against Fusarium oxysporum f. xanthophyllosis in microtiter plate test

[0400] Mix the stock solution according to the specified ratio, transfer it to a microtiter plate (MTP) using a pipette, and dilute with water to the specified concentration. Then add a spore suspension of *Fusarium oxysporum* in bio-malt or yeast-bacterial peptone-sodium acetate aqueous solution. Place these plates in a water vapor saturated chamber at 18°C. Measure the MTP at 405 nm using an absorbance spectrophotometer 7 days after inoculation.

[0401] In this test, samples treated with 31 ppm of active material from Examples Ex-3 and Ex-4 showed a pathogen growth rate of up to 18%.

[0402] greenhouse

[0403] The compound was dissolved in a mixture of acetone and / or dimethyl sulfoxide and Wettol, an ethoxylated alkylphenol-based wetting / emulsifier, at a solvent-emulsifier ratio (volume) of 99:1, to obtain a total volume of 5 ml. Water was then added to a total volume of 100 ml.

[0404] This stock solution is then diluted with the solvent-emulsifier-water mixture to the final concentration given in the table below.

[0405] Example 1 - Preventive fungicidal control of Botrytis cinerea on bell pepper leaves

[0406] Bell pepper seedlings were grown in pots to the 4-5 leaf stage. These plants were sprayed to drip rate with the aforementioned spray solution, which contains the active ingredients or mixtures mentioned in the table below at concentrations. The next day, the plants were inoculated with a biological malt or DOB aqueous solution containing a suspension of Botrytis cinerea spores. The plants were then immediately transferred to a humid environment. After 5 days at 22°C to 24°C and saturated relative humidity, the extent of fungal infection on the leaves was visually assessed as a percentage of diseased leaf area.

[0407] In this test, the sample treated with 80 ppm of active substance from Example Ex-4 showed a 14% increase in pathogen growth rate, while 90% of the untreated plants were infected.

Claims

1. A compound of formula I and N-oxides and the agriculturally acceptable salts thereof, as fungicide, wherein R 1 selected from the group consisting of Ci-C6-alkyl, 0-Ci-C6-alkyl, S-Ci-C6-alkyl, halogen, Ci-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, C3-C6-cycloalkyl; R 2 is selected from the group consisting of H, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, benzyl, a heterocyclic aromatic moiety and CH2-heterocyclic aromatic moiety, wherein the moieties are unsubstituted or substituted by one to three groups R, independently of one another, selected from 2a substituted: halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, 0-Ci-C6-alkyl; R 3 is selected from the group consisting of H, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, C2-C6-haloalkynyl, phenyl, benzyl, a heterocyclic aromatic moiety and CH2-heterocyclic aromatic moiety, wherein the moieties are unsubstituted or substituted by one to three groups R, independently of one another, selected from 3a substituted: halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, 0-Ci-C6-alkyl; or R 2 and R 3 together with the C atom to which they are bound form C=O; or R 2 and R 3 together with the C atom to which they are bound form a 3-, 4-, 5- or 6-membered saturated carbocyclic ring or a 3-, 4-, 5- or 6-membered saturated heterocyclic ring having 1, 2 or 3 heteroatoms selected from O, N and S as ring members, wherein the moieties are unsubstituted or substituted by 1, 2 or 3 substituents R, independently of one another, selected from 23 substituted: halogen, Ci-C6-alkyl or Ci-C6-haloalkyl; X 1 selected from the group consisting of H, halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, C2- C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, phenyl, benzyl, O-phenyl, O-benzyl, S- phenyl, S-benzyl, wherein the cyclic moieties are unsubstituted or substituted by one to three groups R independently of one another selected from X1 substituted: halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, 0-Ci-C6-alkyl; X 2 selected from the group consisting of H, halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, C2- C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, phenyl, benzyl, O-phenyl, O-benzyl, S- phenyl, S-benzyl; wherein the cyclic moieties are unsubstituted or substituted by one to three groups R independently of one another selected from X2 substituted: halogen, CN, Ci-C6-alkyl, Ci-C6-haloalkyl, 0-Ci-C6-alkyl.

2. The compound of claim 1, wherein, R 1 is C1-C6-alkyl.

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

4. The compound of any one of claims 1 to 3, wherein, R 2 is H or Ci-C6-alkyl.

5. The compound of any one of claims 1 to 4, wherein, R 2 is H or CH3.

6. The compound of any one of claims 1 to 5, wherein, R 3 is H or Ci-C6-alkyl.

7. The compound of any one of claims 1 to 6, wherein, R 3 is H or CH3.

8. The compound of any one of claims 1 to 7, wherein, X 1 selected from halogen.

9. The compound of any one of claims 1 to 8, wherein, X 2 is H or halogen.

10. The compound of any one of claims 1 to 9, wherein, X 1 is CH3.

11. The compound of any one of claims 1 to 10, wherein, X 2 is OCH3.

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

13. A method of combating phytopathogenic fungi, which comprises treating the fungi or the materials, plants, soils or seeds to be protected from fungal attack with an effective amount of at least one compound of formula I, as defined in any of claims 1 to 11, or with a composition as defined in any of claim 12.

14. A seed coated with 0.1 to 10 kg per 100 kg of seed of at least one compound of formula I, or an agriculturally acceptable salt thereof, as defined in any of claims 1 to 11, or a composition as defined in any of claim 12.

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