Substitute pyridyl / pyrazidyldihydrobenzothiazepine compounds for eradicating plant pathogenic fungi

Abstract

The present invention relates to formula (I) [Formula 1] TIFF2026509904000069.tif26170 (wherein the formula, the variables are defined as shown herein and in the claims) This invention relates to compounds. The present invention further relates to their uses and compositions.

Description

[Technical Field]

[0001] The present invention relates to novel pyridyl / pyradidyldihydrobenzothiazepine compounds as fungicides, their N-oxides and salts, and their uses. The present invention also relates to compositions comprising at least one compound I, methods for controlling plant pathogenic fungi, and seeds coated with at least one compound of formula I. [Background technology]

[0002] Several dihydrobenzothiazepine compounds are disclosed in International Publication No. 2010018686. However, in many cases, especially at low application rates, the fungicidal activity of known compounds is unsatisfactory. Based on this, an object of the present invention was to provide compounds having 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 pharmacokinetic properties. [Overview of the project] [Means for solving the problem]

[0003] These and further objectives are achieved by dihydrobenzothiazepine compounds of formula (I) as defined below, and by agriculturally suitable salts thereof. [Modes for carrying out the invention]

[0004] Therefore, the present invention relates to Formula I [ka] (Y is N, CR 1 and; Z is S, SO, or SO2. R 1 In each case, the elements are independently selected from H, halogen, CN, C1-C4 alkyl, and C1-C4 halogen alkyl; R2 is independently selected in each case from halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, O-C1-C6 alkyl, O-C2-C6 alkenyl, O-C2-C6 alkynyl, C3-C6 cycloalkyl, S-C1-C6 alkyl, S-C2-C6 alkenyl, S-C2-C6 alkynyl; R 3 is independently selected in each case from halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, O-C1-C6 alkyl, O-C2-C6 alkenyl, O-C2-C6 alkynyl, C3-C6 cycloalkyl, S-C1-C6 alkyl, S-C2-C6 alkenyl, S-C2-C6 alkynyl; R 4 is independently selected in each case from H, halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl; R 5 is independently selected in each case from hydrogen, halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, phenyl, benzyl, 5- or 6-membered heteroaryl or 5- or 6-membered CH2-heteroaryl; heteroaryl contains 1, 2 or 3 heteroatoms selected from N, O and S; the aliphatic or aromatic group is unsubstituted or has 1, 2 or 3 substituents R 5a ; each R 5a is independently halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl or O-C1-C6 alkyl; R 6In each case, is independently selected from hydrogen, halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, phenyl, benzyl, 5- or 6-membered heteroaryl, or 5- or 6-membered CH2-heteroaryl; the heteroaryl contains 1, 2, or 3 heteroatoms selected from N, O, and S; the aliphatic or aromatic group is unsubstituted or has 1, 2, or 3 substituents R 6a Having; Each R 6a These are independently halogens, CN, C1-C6 alkyl, C1-C6 haloalkyl, or O-C1-C6 alkyl; Or, R 5 and R 6 They both form an oxo group (=O); or a thioxo group (=S); Or, R 5 and R 6 Together with the carbon atoms to which they are bonded, they form a 3-membered, 4-membered, 5-membered, or 6-membered saturated carbocyclic ring or a 3-membered, 4-membered, 5-membered, or 6-membered saturated heterocyclic ring containing 1, 2, or 3 heteroatoms selected from O and S as ring members; the carbocyclic ring or heterocyclic ring is unsubstituted or has 1, 2, or 3 substituents R 56 Having; Each R 56 These are independently halogens, C1-C6 alkyls, or C1-C6 haloalkyls; R 7 In each case, the group is independently selected from hydrogen, halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, phenyl, benzyl, a 5- or 6-membered heteroaryl, or a 5- or 6-membered CH2 heteroaryl; the heteroaryl contains 1, 2, or 3 heteroatoms selected from N, O, and S; the aliphatic or aromatic group is unsubstituted or has 1, 2, or 3 substituents R 7a Having; Each R 7aThese are independently halogens, CN, C1-C6 alkyl, C1-C6 haloalkyl, or O-C1-C6 alkyl; R 8 In each case, the group is independently selected from hydrogen, halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, phenyl, benzyl, a 5- or 6-membered heteroaryl, or a 5- or 6-membered CH2 heteroaryl; the heteroaryl contains 1, 2, or 3 heteroatoms selected from N, O, and S; the aliphatic or aromatic group is unsubstituted or has 1, 2, or 3 substituents R 8a Having; Each R 8a These are independently halogens, CN, C1-C6 alkyl, C1-C6 haloalkyl, or O-C1-C6 alkyl; Or, R 7 and R 8 Together with the carbon atoms to which they are bonded, they form a 3-membered, 4-membered, 5-membered, or 6-membered saturated carbon ring or a 3-membered, 4-membered, 5-membered, or 6-membered saturated heterocycle containing 1, 2, or 3 heteroatoms selected from O and S as ring members; In each case, X is independently selected from halogens, CN, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C1-C6 alkoxy or C1-C6 haloalkoxy, phenyl, benzyl, phenoxy, benzoxy, and C1-C6 thioalkyl; phenyl, benzyl, phenoxy, and benzoxy may be unsubstituted or substituted with halogens, CN, C1-C6 alkyl, or C1-C6 haloalkyl; n is 0, 1, 2, or 3; however, Y is CR 1 If R 5 , R 6 , R 7 and R 8 (It is not possible for all of them to be H.) This relates to compounds, or their N-oxides, tautomers, stereoisomers, or agriculturally acceptable salts.

[0005] N-oxides can be prepared from the compounds of the present invention by treating compound I with conventional oxidation methods, such as organic peracids like metachloroperbenzoic acid (see International Publication No. 03 / 64572 or J.Med.Chem. 38(11), 1892-903, 1995); or inorganic oxidizing agents like hydrogen peroxide (see J.Heterocyc.Chem. 18(7), 1305-8, 1981); or oxone (see J.Am.Chem.Chem.Soc. 123(25), 5962-5973, 2001). Oxidation may yield a pure mono-N-oxide or a mixture of different N-oxides, which can be separated by conventional methods such as chromatography.

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

[0007] The acceptable anions for acid addition salts are mainly those of chlorides, bromides, fluorides, hydrogen sulfates, sulfates, dihydrogen phosphates, hydrogen phosphates, phosphates, nitrates, bicarbonates, carbonates, hexafluorosilicates, hexafluorophosphates, benzoates, and C1-C4 alkanic acids, preferably formates, acetates, propionates, and butyrates. These can be formed by reacting compound I with the acid of the corresponding anion, preferably hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid, or nitric acid.

[0008] Compounds of formula I can exist as one or more stereoisomers. Various stereoisomers include enantiomers, diastereomers, atropisomers arising from binding rotations around single bonds of chiral groups, and geometric isomers. These also form part of the subject matter of the present invention. Those skilled in the art will understand that a certain stereoisomer may be more active and / or exhibit beneficial effects when concentrated relative to other stereoisomers or when separated from other stereoisomers. In addition, those skilled in the art know methods for separating, concentrating, and / or selectively preparing such stereoisomers. The compounds of the present invention can exist as mixtures of stereoisomers, e.g., racemic compounds, individual stereoisomers, or optically active compounds.

[0009] Compounds of formula I can exist in different crystalline transformations, which may have different biological activities. These also form part of the subject matter of the present invention.

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

[0011] The intermediate compounds are described further below. Those skilled in the art will readily understand that the preferences for substituents, in particular those shown herein in relation to Compound I and shown in the table below for each substituent, also apply to the intermediates accordingly. Thus, the substituents in each case, independently or more preferably in combination, have the meanings defined herein.

[0012] When a mixture of isomers is obtained by synthesis, separation is generally not always necessary, as individual isomers may interconvert during post-treatment or application (e.g., under the action of light, acid, or base). Such conversions may also occur after use, for example, in the treatment of plants in treated plants or in harmful fungi being controlled.

[0013] In the definition of the above variables, a general term that generally represents the substituent in question is used. n ~C m The term "substituent" indicates the number of carbon atoms possible in the substituent or substituent moiety in each case.

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

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

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

[0017] The term "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 include "C2-C4 alkenyl" groups, such as ethenyl, 1-propenyl, 2-propenyl(allyl), 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, and 2-methyl-2-propenyl.

[0018] The term "C2-C6 halogen alkenyl" refers to alkyl groups having two or six carbon atoms as defined above, in which some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as described above.

[0019] The term "C2-C6 alkynyl" refers to a linear or branched unsaturated hydrocarbon group having 2 to 6 carbon atoms and containing at least one triple bond. Examples include "C2-C4 alkynyl" groups, such as ethynyl, prop-1-inyl, prop-2-inyl (propargyl), buto-1-inyl, buto-2-inyl, buto-3-inyl, and 1-methyl-prop-2-inyl.

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

[0021] The term "C3-C6 cycloalkyl" refers to monocyclic saturated hydrocarbon groups having 3 to 6 carbon ring members, such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. Therefore, saturated 3-membered, 4-membered, 5-membered, 6-membered, 7-membered, 8-membered, 9-membered, or 10-membered carbocyclyl or carbon ring is "C3-C 10 It is a "cycloalkyl" compound.

[0022] The term "C3-C8 cycloalkyl-C1-C4 alkyl" refers to alkyl groups having 1-4 carbon atoms (as defined above), in which at least one hydrogen atom of the alkyl group is replaced by a cycloalkyl group having 3-8 carbon atoms (as defined above).

[0023] The term "saturated or partially unsaturated 3-membered, 4-membered, 5-membered, 6-membered, 7-membered, 8-membered, 9-membered or 10-membered heterocyclyl or heterocycle containing 1, 2, 3 or 4 heteroatoms selected from N, O, and S" should be understood to mean both saturated and partially unsaturated heterocycles, where the ring-member atoms of the heterocycle include carbon atoms plus 1, 2, 3 or 4 heteroatoms independently selected from the group O, N, and S. For example: Three- or four-membered saturated heterocycles containing one or two heteroatoms from the group consisting of O, N, and S as ring members, such as oxiran, aziridine, thiran, oxetane, azetidine, thietan, [1,2]dioxetane, [1,2]dithietan, [1,2]diazetidine; and Five-membered or six-membered saturated or partially unsaturated heterocycles containing one, two, or three heteroatoms from the group consisting of O, N, and S as ring members, such as 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxy Sazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1,2,4-triazolidine-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidine-2-yl, 2,3-dihydroflu-2-yl, 2,3 -Dihydrofluor-3-yl, 2,4-Dihydrofluor-2-yl, 2,4-Dihydrofluor-3-yl, 2,3-Dihydrothien-2-yl, 2,3-Dihydrothien-3-yl, 2,4-Dihydrothien-2-yl, 2,4-Dihydrothien-3-yl, 2-Pyrroline-2-yl, 2-Pyrroline-3-yl, 3-Pyrroline-2-yl, 3-Pyrroline-3-yl, 2-Isoxazolin-3-yl, 3-Isoxazolin-3-yl, 4-Isoxazolin-3-yl, 2-Isoxazolin-4-yl, 3-Isoxazolin-4-yl, 4-Isoxazo Phosphate-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-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 Lu-4-yl, 3,4-dihydroxazol-5-yl, 3,4-dihydroxazol-2-yl, 3,4-dihydroxazol-3-yl, 3,4-dihydroxazol-4-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1,3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, 1,3,5-hexahydrotriazine-2-yl and 1,2,4-hexahydrotriazine-3-yl and the corresponding -ylidene group; and, 7-membered saturated or partially unsaturated heterocycles, e.g., tetra- and hexahydroazepinyl, e.g., 2,3,4,5-tetrahydro[1H]azepine-1-,-2-,-3-,-4-,-5-,-6- or-7-yl, 3,4,5,6-tetrahydro[2H]azepine-2-,-3-,-4-,-5-,-6- or-7-yl, 2,3,4,7-tetrahydro[1H] Azepine-1-,-2-,-3-,-4-,-5-,-6- or-7-yl, 2,3,6,7-tetrahydro[1H]azepine-1-,-2-,-3-,-4-,-5-,-6- or-7-yl, hexahydroazepine-1-,-2-,-3- or-4-yl, tetra- and hexahydrooxepinyl, e.g., 2,3,4,5-tetrahydro[1H]oxepine-yl Sepin-2-,-3-,-4-,-5-,-6- or-7-yl, 2,3,4,7-tetrahydro[1H]oxepin-2-,-3-,-4-,-5-,-6- or-7-yl, 2,3,6,7-tetrahydro[1H]oxepin-2-,-3-,-4-,-5-,-6- or-7-yl, hexahydroazepine-1-,-2-,-3- or-4-yl, Tetra- and hexahydro-1,3-diazepinyl, tetra- and hexahydro-1,4-diazepinyl, tetra- and hexahydro-1,3-oxazepinyl, tetra- and hexahydro-1,4-oxazepinyl, tetra- and hexahydro-1,3-dioxepinyl, tetra- and hexahydro-1,4-dioxepinyl, and the corresponding -ylidene group That is the case.

[0024] The term "substituted" refers to a state where a substituent is substituted with one, two, three, or up to the maximum possible number of substituents.

[0025] The terms "5-membered or 6-membered heteroaryl" or "5-membered or 6-membered heteroaromatic" refer to aromatic ring systems containing, in addition to carbon atoms, one, two, three, or four heteroatoms independently selected from the group consisting of N, O, and S, for example, Five-membered heteroaryls, e.g., pyrrole-1-yl, pyrrole-2-yl, pyrrole-3-yl, thien-2-yl, thien-3-yl, fran-2-yl, fran-3-yl, pyrazole-1-yl, pyrazole-3-yl, pyrazole-4-yl, pyrazole-5-yl, imidazole-1-yl, imidazole-2-yl, imidazole-4-yl, imidazole-5-yl, oxazole-2-yl, oxazole-4-yl, oxazole-5-yl, isoxazole-3-yl, isoxazole-4-yl, isoxazole-5-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1,2,4-triazolyl-1-yl, 1,2,4-triazol-3-yl 1,2,4-triazole-5-yl, 1,2,4-oxadiazole-3-yl, 1,2,4-oxadiazole-5-yl and 1,2,4-thiadiazole-3-yl, 1,2,4-thiadiazole-5-yl; or Six-membered heteroaryls, such as pyridine-2-yl, pyridine-3-yl, pyridine-4-yl, pyridazine-3-yl, pyridazine-4-yl, pyrimidine-2-yl, pyrimidine-4-yl, pyrimidine-5-yl, pyrazine-2-yl, and 1,3,5-triazine-2-yl and 1,2,4-triazine-3-yl It refers to.

[0026] Specific embodiments of the compounds of the present invention are described below. Therein, the specific meaning of each substituent is further detailed, and in each case, the meaning is specific to the present invention, not only in itself but also in any combination thereof.

[0027] Furthermore, with respect to the variables, the embodiment of compound I is generally applicable to intermediates as well.

[0028] According to one embodiment of the compound of formula I, Y is N.

[0029] According to one embodiment of the compound of formula I, Y is CR 1 That is the case.

[0030] According to one embodiment of the compound of formula I, Z is S.

[0031] According to one embodiment of the compound of formula I, Z is SO.

[0032] According to one embodiment of the compound of formula I, Z is SO2.

[0033] According to one embodiment of the compound of formula I, R 1 In each case, is independently selected from H, halogen, CN, C1-C4 alkyl, and C1-C4 halogen alkyl, and is preferred R 1 In each case, R is independently selected from H, C1-C4 alkyl, and C1-C4 halogen alkyl, with R being more preferred. 1 In each case, H is independently selected from C1-C4 alkyl groups, and the most preferred R is... 1 In each case, H is the value.

[0034] According to one embodiment of the compound of formula I, R 2 The following are selected: halogen, CN, C1-C6 alkyl, C1-C6 halogen alkyl, C2-C6 alkenyl, C2-C6 halogen alkenyl, C2-C6 alkynyl, C2-C6 halogen alkynyl, O-C1-C6 alkyl, O-C2-C6 alkenyl, O-C2-C6 alkynyl, C3-C6 cycloalkyl, S-C1-C6 alkyl, S-C2-C6 alkenyl, and S-C2-C6 alkynyl.

[0035] According to one embodiment of the compound of formula I, R 2 In each case, the preferred R is independently selected from C1-C4 alkyl and C1-C4 halogen alkyl. 2 In each case, R is independently selected from H, C1-C4 alkyl, and C1-C4 halogen alkyl, with R being more preferred. 2 In each case, the most preferred R is independently selected from CH3 and CF2H. 2In each case, it is CH3.

[0036] According to yet another embodiment of formula I, R 2 These are halogens, particularly F, Cl, Br, or I, more specifically F, Cl, or Br, particularly F or Cl.

[0037] According to yet another embodiment of formula I, R 2 It is F.

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

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

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

[0041] According to yet another embodiment of formula I, R 2 These are C1-C6 alkyl groups, especially C1-C4 alkyl groups, such as CH3 or C2H5, especially CH3 or CH2CH3.

[0042] According to yet another embodiment of formula I, R 2 These are C1-C6 halogen alkyls, particularly C1-C4 halogen alkyls, such as CF3.

[0043] According to a further embodiment of formula I, R 2 These are C2-C6 alkenyls, especially C2-C4 alkenyls, such as CH=CH2, C(CH3)=CH2, and CH2CH=CH2.

[0044] According to a more specific embodiment of formula I, R 2These are C2-C6 halogen alkenyls, especially C2-C4 halogen alkenyls, and more specifically C2-C3 halogen alkenyls, such as CH=CHF, CH=CHCl, CH=CF2, CH=CCl2, CH2CH=CHF, CH2CH=CHCl, CH2CH=CF2, CH2CH=CCl2, CF2CH=CF2, CCl2CH=CCl2, CF2CF=CF2, and CCl2CCl=CCl2.

[0045] According to a further embodiment of formula I, R 2 These are C2-C6 alkynyl or C2-C6 halogen alkynyl, particularly C2-C4 alkynyl or C2-C4 halogen alkynyl, for example, C≡CH, CH2C≡CH, C≡CCl, CH2C≡CCl, or CCl2C≡CCl.

[0046] According to a further specific embodiment of formula I, R 2 These are O-C1~C6 alkyl groups, especially C1~C4 alkyl groups, and more specifically C1~C2 alkoxy groups. 2 For example, these are OCH3 or OCH2CH3.

[0047] According to a further specific embodiment of formula I, R 2 These are O-C1~C6 alkyl groups.

[0048] According to a further specific embodiment of formula I, R 2 These are O-C2~C6 alkenyls, especially C2~C4 alkenyls, and more specifically C2~C3 alkenyls. 2 For example, OCH=CH2 and OCH2CH=CH2.

[0049] According to a further specific embodiment of formula I, R 2 These are O-C2~C6 alkynyl compounds, especially C2~C6 alkynyl compounds, especially C2~C4 alkynyl compounds, and more specifically C2~C3 alkynyl compounds. 2 For example, O-CH2-C≡CH.

[0050] According to yet another embodiment of formula I, R 2These are C3-C6 cycloalkyl groups, particularly cyclopropyl or cyclobutyl groups.

[0051] According to a further specific embodiment of formula I, R 2 These are S-C1~C6 alkyl groups, especially C1~C4 alkyl groups, and more specifically C1~C2 alkoxy groups. 2 For example, these are SCH3 or SCH2CH3.

[0052] According to a further specific embodiment of formula I, R 2 These are S-C1~C6 alkyl groups.

[0053] According to a further specific embodiment of formula I, R 2 These are S-C2~C6 alkenyls, especially C2~C4 alkenyls, and more specifically C2~C3 alkenyls. 2 For example, SCH=CH2 and SCH2CH=CH2.

[0054] According to a further specific embodiment of formula I, R 2 These are S-C2~C6 alkynyl compounds, especially C2~C6 alkynyl compounds, especially C2~C4 alkynyl compounds, and more specifically C2~C3 alkynyl compounds. 2 For example, S-CH2-C≡CH.

[0055] R according to the present invention 2 Particularly preferred embodiments are shown in Table P2 below, where each row from P2-1 to P2-21 corresponds to a specific embodiment of the present invention, and P2-1 to P2-21 can also be arbitrarily combined to constitute preferred embodiments of the present invention. 2 The connection point to the carbon atom to which it is bonded is indicated by "#" in the diagram.

[0056] [Table 1]

[0057] According to one embodiment of formula I, R 3The group is selected from C1-C6 alkyl, C1-C6 halogen alkyl, C3-C6 cycloalkyl, particularly CH3, C2H5, CF3, CH2F, CHF2, cyclopropyl, cyclobutyl, more specifically CH3, CH2F, CF2H, CF3, cyclopropyl, cyclobutyl, most preferably CH3, CF2H.

[0058] According to yet another embodiment of formula I, R 3 These are C1-C6 alkyl groups, especially C1-C4 alkyl groups, such as CH3 or C2H5, especially CH3 or CH2CH3.

[0059] According to yet another embodiment of formula I, R 3 These are C1-C6 halogen alkyl groups, especially C1-C4 halogen alkyl groups, such as CF3, FCH2, F2CH, and CF3CH2.

[0060] According to a further embodiment of formula I, R 3 These are C2-C6 alkenyls, especially C2-C4 alkenyls, such as CH=CH2, C(CH3)=CH2, and CH2CH=CH2.

[0061] According to a further embodiment of formula I, R 3 These are C2-C6 alkynyl or C2-C6 halogen alkynyl, particularly C2-C4 alkynyl or C2-C4 halogen alkynyl, for example, C≡CH, CH2C≡CH, C≡CCl, CH2C≡CCl, or CCl2C≡CCl.

[0062] According to a further specific embodiment of formula I, R 3 These are O-C1~C6 alkyl groups, especially C1~C4 alkyl groups, and more specifically C1~C2 alkoxy groups. 3 For example, these are OCH3 or OCH2CH3.

[0063] According to a further specific embodiment of formula I, R 3 These are O-C2~C6 alkenyls, especially C2~C4 alkenyls, and more specifically C2~C3 alkenyls. 3For example, OCH=CH2 and OCH2CH=CH2.

[0064] According to a further specific embodiment of formula I, R 3 These are O-C2~C6 alkynyl compounds, especially C2~C6 alkynyl compounds, especially C2~C4 alkynyl compounds, and more specifically C2~C3 alkynyl compounds. 3 For example, O-CH2-C≡CH.

[0065] According to a further specific embodiment of formula I, R 3 These are O-C1~C6 halogen alkyls, particularly OCF3, OCl3, OFCH2, OClCH2, OF2CH, OCl2CH, OCF3CH2, OCl3CH2 or OCF2CHF2, more specifically OCF3, OF2CH, OFCH2.

[0066] According to yet another embodiment of formula I, R 3 These are C3-C6 cycloalkyl groups, particularly cyclopropyl and cyclobutyl compounds.

[0067] According to a further specific embodiment of formula I, R 3 These are S-C1~C6 alkyl groups, especially C1~C4 alkyl groups, and more specifically C1~C2 alkoxy groups. 2 For example, these are SCH3 or SCH2CH3.

[0068] According to a further specific embodiment of formula I, R 3 These are S-C1~C6 alkyl groups.

[0069] According to a further specific embodiment of formula I, R 3 These are S-C2~C6 alkenyls, especially C2~C4 alkenyls, and more specifically C2~C3 alkenyls. 2 For example, SCH=CH2 and SCH2CH=CH2.

[0070] According to a further specific embodiment of formula I, R 3is S-C2-C6 alkynyl, especially C2-C6 alkynyl, especially C2-C4 alkynyl, more specifically C2-C3 alkynyl. R 2 is, for example, S-CH2-C≡CH.

[0071] R according to the present invention 3 A particularly preferred embodiment of is in Table P3 below. Each row of P3-1 to P3-17 corresponds to a specific embodiment of the present invention, and P3-1 to P3-17 are also preferred embodiments of the present invention when arbitrarily combined with each other. The connection point for the carbon atom to which R 3 is attached is indicated by "#" in the drawings.

[0072]

Table 2

[0073]

Table 3

[0074] According to one embodiment of the compound of formula I, R 4 is independently selected from H, halogen, CN, C1-C4 alkyl, C1-C4 haloalkyl in each case, and preferred R 4 is independently selected from H, C1-C4 alkyl, C1-C4 haloalkyl in each case, and more preferred R 4 is independently selected from H, C1-C4 alkyl in each case, and most preferred R 4 is H in each case.

[0075] According to one embodiment of the compound of formula I, R 5In each case, the group is independently selected from hydrogen, halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, phenyl, benzyl, a 5- or 6-membered heteroaryl, or a 5- or 6-membered CH2 heteroaryl; the heteroaryl contains 1, 2, or 3 heteroatoms selected from N, O, and S; the aliphatic or aromatic group is unsubstituted or has 1, 2, or 3 substituents R 5a It has; each R 5a These are independently halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, or O-C1-C6 alkyl.

[0076] According to one embodiment of the compound of formula I, R 5 In each case, the elements are independently selected from C1-C6 alkyl (Embodiment 5.1), C1-C6 halogen alkyl (Embodiment 5.2), C1-C6 alkyl-O-C1-C6 alkyl (Embodiment 5.3), phenyl, and CH2-phenyl (Embodiment 5.4), where phenyl and CH2-phenyl are either unsubstituted or substituted with one or two halogens.

[0077] According to a further embodiment of the compound of formula I, R 5 It is either CH3 or CF3.

[0078] According to a further embodiment of the compound of formula I, R 5 This is CH3.

[0079] According to a further embodiment of the compound of formula I, R 5 are CH2CH3, CH(CH3)2, CH(CH3)CH2CH3, C(CH3)3, CH2-CH(CH3)2, CH2-C(CH3)3, CH2-O-CH3.

[0080] According to a further embodiment of the compound of formula I, R 5 CH=CH2 and CH2CH=CH2.

[0081] According to a further embodiment of the compound of formula I, R 5 These are phenyl, 2-F-phenyl, 4-F-phenyl, 2,4-F2-phenyl, 2-Cl-phenyl, 4-Cl-phenyl, CH2-phenyl, CH2-2-F-phenyl, and CH2-4-F-phenyl.

[0082] According to one embodiment of the compound of formula I, R 6 In each case, the group is independently selected from hydrogen, halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, phenyl, benzyl, a 5- or 6-membered heteroaryl, or a 5- or 6-membered CH2 heteroaryl; the heteroaryl contains 1, 2, or 3 heteroatoms selected from N, O, and S; the aliphatic or aromatic group is unsubstituted or has 1, 2, or 3 substituents R 6a It has; each R 6a These are independently halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, or O-C1-C6 alkyl.

[0083] According to one embodiment of the compound of formula I, R 6 In each case, the elements are independently selected from C1-C6 alkyl (Embodiment 6.1), C1-C6 alkyl-O-phenyl (Embodiment 6.2), and C1-C6 alkyl-O-C1-C6 alkyl (Embodiment 6.3).

[0084] According to a further embodiment of the compound of formula I, R 6 These are CH2CH3, CH(CH3)2, CH(CH3)CH2CH3, C(CH3)3, CH2-CH(CH3)2, CH2-C(CH3)3, CH2-CH(CH3)-C(CH3)3, CH2-CH2-C(CH3)3, CH2-O-CH3, CH2-O-(CH3)3, CH2-O-phenyl, and CH=CH2, CH2CH=CH2, CH2-phenyl.

[0085] According to a further embodiment of the compound of formula I, R5 and R 6 Together with the C atom to which they are bonded, they form a 3- to 6-membered saturated heterocycle containing one, two, or three heteroatoms from the group consisting of C3-C6 cycloalkyl or O and S, wherein the cycloalkyl or heterocycle may be unsubstituted or substituted with halogen, C1-C6 alkyl, or C1-C6 halogenalkyl.

[0086] According to a further embodiment of the compound of formula I, R 5 and R 6 This forms a C3-C6 cycloalkyl group (Embodiment 6.4).

[0087] According to a further embodiment of the compound of formula I, R 5 and R 6 It forms a 3- to 6-membered saturated heterocycle containing 1, 2, or 3 heteroatoms from the group consisting of O and S.

[0088] According to a further embodiment of the compound of formula I, R 5 and R 6 These together form an (=O) group (Embodiment 6.5).

[0089] R according to the present invention 5 , R 6 Preferred embodiments are shown in Table P5 below, where rows P5-1 to P5-19 correspond to a specific embodiment of the present invention, and P5-1 to P5-19 can also be arbitrarily combined to constitute preferred embodiments of the present invention. 5 and R 6 The connection point to the carbon atom to which it is bonded is indicated by "#" in the diagram.

[0090] [Table 4]

[0091] [Table 5]

[0092] According to one embodiment of the compound of formula I, R 7 In each case, the group is independently selected from hydrogen, halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, phenyl, benzyl, a 5- or 6-membered heteroaryl, or a 5- or 6-membered CH2 heteroaryl; the heteroaryl contains 1, 2, or 3 heteroatoms selected from N, O, and S; the aliphatic or aromatic group is unsubstituted or has 1, 2, or 3 substituents R 7a It has; each R 7a These are independently halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, or O-C1-C6 alkyl.

[0093] According to one embodiment of the compound of formula I, R 7 In each case, the elements are independently selected from C1-C6 alkyl (Embodiment 7.1), C1-C6 halogen alkyl (Embodiment 7.2), C1-C6 alkyl-O-C1-C6 alkyl (Embodiment 7.3), phenyl, and CH2-phenyl (Embodiment 7.4), where phenyl and CH2-phenyl are either unsubstituted or substituted with one or two halogens.

[0094] According to a further embodiment of the compound of formula I, R 7 It is either CH3 or CF3.

[0095] According to a further embodiment of the compound of formula I, R 7 This is CH3.

[0096] According to a further embodiment of the compound of formula I, R 7 are CH2CH3, CH(CH3)2, CH(CH3)CH2CH3, C(CH3)3, CH2-CH(CH3)2, CH2-C(CH3)3, CH2-O-CH3, CH=CH2, CH2CH=CH2.

[0097] According to a further embodiment of the compound of formula I, R7 These are phenyl, 2-F-phenyl, 4-F-phenyl, 2,4-F2-phenyl, 2-Cl-phenyl, 4-Cl-phenyl, CH2-phenyl, CH2-2-F-phenyl, and CH2-4-F-phenyl.

[0098] According to one embodiment of the compound of formula I, R 8 In each case, the group is independently selected from hydrogen, halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, C2-C6 alkenyl, C2-C6 haloalkenyl, C2-C6 alkynyl, C2-C6 haloalkynyl, phenyl, benzyl, a 5- or 6-membered heteroaryl, or a 5- or 6-membered CH2 heteroaryl; the heteroaryl contains 1, 2, or 3 heteroatoms selected from N, O, and S; the aliphatic or aromatic group is unsubstituted or has 1, 2, or 3 substituents R 8a It has; each R 8a These are independently halogen, CN, C1-C6 alkyl, C1-C6 haloalkyl, or O-C1-C6 alkyl.

[0099] According to one embodiment of the compound of formula I, R 8 In each case, the following are independently selected from C1-C6 alkyl (Embodiment 8.1), C1-C6 alkyl-O-phenyl (Embodiment 8.2), and C1-C6 alkyl-O-C1-C6 alkyl (Embodiment 8.3).

[0100] According to a further embodiment of the compound of formula I, R 8 These are CH2CH3, CH(CH3)2, CH(CH3)CH2CH3, C(CH3)3, CH2-CH(CH3)2, CH2-C(CH3)3, CH2-CH(CH3)-C(CH3)3, CH2-CH2-C(CH3)3, CH2-O-CH3, CH2-O-(CH3)3, CH2-O-phenyl, CH=CH2, CH2CH=CH2, and CH2-phenyl.

[0101] According to a further embodiment of the compound of formula I, R 7 and R 8Together with the C atom to which they are bonded, they form a 3- to 6-membered saturated heterocycle containing one, two, or three heteroatoms from the group consisting of C3-C6 cycloalkyl or O and S, wherein the cycloalkyl or heterocycle may be unsubstituted or substituted with halogen, C1-C6 alkyl, or C1-C6 halogenalkyl.

[0102] According to a further embodiment of the compound of formula I, R 7 and R 8 This forms a C3-C6 cycloalkyl group (Embodiment 8.4).

[0103] According to a further embodiment of the compound of formula I, R 7 and R 8 It forms a 3- to 6-membered saturated heterocycle containing 1, 2, or 3 heteroatoms from the group consisting of O and S.

[0104] R according to the present invention 7 , R 8 Preferred embodiments are shown in Table P78 below, where rows P7-1 to P7-19 correspond to a particular embodiment of the present invention, and P7-1 to P7-19 can also be arbitrarily combined to constitute preferred embodiments of the present invention. 7 and R 8 The connection point to the carbon atom to which it is bonded is indicated by "#" in the diagram.

[0105] [Table 6]

[0106] According to one embodiment of the compound of formula I, X is independently selected in each case from halogen (embodiment X.1), CN, C1-C6 alkyl (embodiment X.2), C1-C6 halogen alkyl (embodiment X.3), O-C1-C6 alkyl (embodiment X.4), and O-C1-C6 halogen alkyl (embodiment X.5).

[0107] According to one embodiment of the compound of formula I, X is independently selected from halogens and O-C1-C6 alkyls in each case.

[0108] According to one embodiment of the compound of formula I, X is independently selected from F or Cl in each case.

[0109] According to one embodiment of the compound of formula I, X is a C3-C6 cycloalkyl group.

[0110] According to one embodiment of the compound of formula I, n is 0.

[0111] According to one embodiment of the compound of formula I, n is 1.

[0112] According to one embodiment of the compound of formula I, n is 2.

[0113] According to one embodiment, Xn is as follows: [ka] As defined, X is selected from F, Cl, I, CH3, cyclopropyl, CH=CH2, C≡CH, OCH3, OCHF2, CF3, CHF2, CH2CH3, CN, and OPh.

[0114] According to one embodiment, Xn is as follows: [ka] As defined, X is F.

[0115] According to one embodiment, Xn is as follows: [ka] As defined, X is selected from F, Cl, I, CH3, cyclopropyl, CH=CH2, C≡CH, OCH3, OCHF2, CF3, CHF2, CH2CH3, CN, and OPh.

[0116] According to one embodiment, Xn is as follows: [ka] As defined, X is F.

[0117] According to one embodiment, n is 0.

[0118] Therefore, according to the present invention, a compound of formula I having one chiral center is A racemic mixture of the (R)-enantiomer and the (S)-enantiomer; - A mixture containing any other ratio of (R)-enantiomer and (S)-enantiomer; -Pure (R)-enantiomer, or -Pure (S)-enantiomer It can be used in this form.

[0119] According to one specific embodiment, the compound of formula I is provided and used as a (R)-enantiomer having an enantiomer excess (ee) 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%.

[0120] According to one specific embodiment, the compound of formula I is provided and used as an (S)-enantiomer having an enantiomer excess (ee) 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%.

[0121] Therefore, according to the present invention, a compound of formula I having two chiral centers is A racemic mixture of the -(R,R)-enantiomer and the (S,S)-enantiomer; - A mixture containing (R,R)-enantiomers and (S,S)-enantiomers in any other ratio; -Pure (R,R)-enantiomer, or -Pure (S,S)-enantiomer It can be used in this form.

[0122] According to one specific embodiment, the compound of formula I is provided and used as a (R,R)-enantiomer having an enantiomer excess (ee) 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%.

[0123] According to one specific embodiment, the compound of formula I is provided and used as an (S,S)-enantiomer having an enantiomer excess (ee) 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%.

[0124] Therefore, according to the present invention, a compound of formula I having two chiral centers is A racemic mixture of -(R,S)-enantiomers and (S,R)-enantiomers; - A mixture containing (R,S)-enantiomers and (S,R)-enantiomers in any other ratio; -Pure (R,S)-enantiomer, or -Pure (S,R)-enantiomer It can be used in this form.

[0125] According to one specific embodiment, the compound of formula I is provided and used as a (R,S)-enantiomer having an enantiomer excess (ee) 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%.

[0126] According to one specific embodiment, the compound of formula I is provided and used as a (S,R)-enantiomer having an enantiomer excess (ee) 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%.

[0127] Therefore, according to the present invention, a compound of formula I having two chiral centers is - A mixture containing (R,S)-diastereomers and (S,S)-diastereomers in any ratio. It can be used in this form.

[0128] According to one specific embodiment, the compound of formula I is provided and used as a (R,S)-diastereomer having a 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%.

[0129] According to one specific embodiment, the compound of formula I is provided and used as a (S,S)-diastereomer having a 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%.

[0130] This applies to mixtures containing any other proportions of mixture A (composed of any proportions of (R,R)-enantiomers and (S,S)-enantiomers) and mixture B (composed of any proportions of (R,S)-enantiomers and (S,R)-enantiomers).

[0131] This also applies to compounds of formula I that have three, four, and five chiral centers.

[0132] In further embodiments, the present invention relates to embodiments E.1 to E.275 listed in Table E, which relate to a compound of formula I as defined below, wherein the variable R 2 , R 3 And each of X (represented by embodiments X.1 to X.6) represents a preferred combination of the embodiments defined above. [ka]

[0133] [Table 7]

[0134] [Table 8]

[0135] [Table 9]

[0136] [Table 10]

[0137] [Table 11]

[0138] [Table 12]

[0139] [Table 13]

[0140] [Table 14]

[0141] [Table 15]

[0142] In a further embodiment, the present invention is R 5 This is represented in Embodiment 5.1, and R 6 This relates to Embodiments E.1 to E.275 listed in Table E, which are represented in Embodiment 6.1.

[0143] In a further embodiment, the present invention is R 5 This is represented in Embodiment 5.2, and R 6 This relates to Embodiments E.1 to E.275 listed in Table E, which are represented in Embodiment 6.1.

[0144] In a further embodiment, the present invention is R 5 This is represented in Embodiment 5.3, and R 6 This relates to Embodiments E.1 to E.275 listed in Table E, which are represented in Embodiment 6.1.

[0145] In a further embodiment, the present invention is R 5 This is represented in Embodiment 5.4, and R 6 This relates to Embodiments E.1 to E.275 listed in Table E, which are represented in Embodiment 6.1.

[0146] In a further embodiment, the present invention is R 5 This is represented in Embodiment 5.1, and R 6This relates to Embodiments E.1 to E.275 listed in Table E, which are represented in Embodiment 6.2.

[0147] In a further embodiment, the present invention is R 5 This is represented in Embodiment 5.2, and R 6 This relates to Embodiments E.1 to E.275 listed in Table E, which are represented in Embodiment 6.2.

[0148] In a further embodiment, the present invention is R 5 This is represented in Embodiment 5.3, and R 6 This relates to Embodiments E.1 to E.275 listed in Table E, which are represented in Embodiment 6.2.

[0149] In a further embodiment, the present invention is R 5 This is represented in Embodiment 5.4, and R 6 This relates to Embodiments E.1 to E.275 listed in Table E, which are represented in Embodiment 6.2.

[0150] In a further embodiment, the present invention is R 5 This is represented in Embodiment 5.1, and R 6 This relates to Embodiments E.1 to E.275 listed in Table E, which are represented in Embodiment 6.3.

[0151] In a further embodiment, the present invention is R 5 This is represented in Embodiment 5.2, and R 6 This relates to Embodiments E.1 to E.275 listed in Table E, which are represented in Embodiment 6.3.

[0152] In a further embodiment, the present invention is R 5 This is represented in Embodiment 5.3, and R 6 This relates to Embodiments E.1 to E.275 listed in Table E, which are represented in Embodiment 6.3.

[0153] In a further embodiment, the present invention is R 5 This is represented in Embodiment 5.4, and R 6 This relates to Embodiments E.1 to E.275 listed in Table E, which are represented in Embodiment 6.3.

[0154] In a further embodiment, the present invention is R 5 and R 6 This relates to Embodiments E.1 to E.275 listed in Table E, which are represented in Embodiment 6.4.

[0155] In a further embodiment, the present invention is R 5 and R 6 This relates to Embodiments E.1 to E.275 listed in Table E, which are represented in Embodiment 6.5.

[0156] In a further embodiment, the present invention is R 7 This is represented in Embodiment 7.1, and R 8 This relates to Embodiments E.1 to E.275 listed in Table E, which are represented in Embodiment 8.1.

[0157] In a further embodiment, the present invention is R 7 This is represented in Embodiment 7.2, and R 8 This relates to Embodiments E.1 to E.275 listed in Table E, which are represented in Embodiment 8.1.

[0158] In a further embodiment, the present invention is R 7 This is represented in Embodiment 7.3, and R 8 This relates to Embodiments E.1 to E.275 listed in Table E, which are represented in Embodiment 8.1.

[0159] In a further embodiment, the present invention is R 7 This is represented in Embodiment 7.4, and R 8 This relates to Embodiments E.1 to E.275 listed in Table E, which are represented in Embodiment 8.1.

[0160] In a further embodiment, the present invention is R 7 This is represented in Embodiment 7.1, and R 8 This relates to Embodiments E.1 to E.275 listed in Table E, which are represented in Embodiment 8.2.

[0161] In a further embodiment, the present invention is R 7is represented by Embodiment 7.2 and R 8 is represented by Embodiment 8.2, and relates to Embodiments E.1 to E.275 listed in Table E.

[0162] In a further aspect, the present invention relates to R 7 is represented by Embodiment 7.3 and R 8 is represented by Embodiment 8.2, and relates to Embodiments E.1 to E.275 listed in Table E.

[0163] In a further aspect, the present invention relates to R 7 is represented by Embodiment 7.4 and R 8 is represented by Embodiment 8.2, and relates to Embodiments E.1 to E.275 listed in Table E.

[0164] In a further aspect, the present invention relates to R 7 is represented by Embodiment 7.1 and R 8 is represented by Embodiment 8.3, and relates to Embodiments E.1 to E.275 listed in Table E.

[0165] In a further aspect, the present invention relates to R 7 is represented by Embodiment 7.2 and R 8 is represented by Embodiment 8.3, and relates to Embodiments E.1 to E.275 listed in Table E.

[0166] In a further aspect, the present invention relates to R 7 is represented by Embodiment 7.3 and R 8 is represented by Embodiment 8.3, and relates to Embodiments E.1 to E.275 listed in Table E.

[0167] In a further aspect, the present invention relates to R 7 is represented by Embodiment 7.4 and R 8 is represented by Embodiment 8.3, and relates to Embodiments E.1 to E.275 listed in Table E.

[0168] In a further aspect, the present invention relates to R 7 and R 8This relates to Embodiments E.1 to E.275 listed in Table E, which are represented in Embodiment 8.4.

[0169] In a further embodiment, the present invention is R 7 and R 8 This relates to Embodiments E.1 to E.275 listed in Table E, which are represented in Embodiment 8.7.

[0170] In particular, from the viewpoint of their use in one embodiment, the compounds IA-1, IA-2, IA-3, IA-4, IA-5, IA-6, IA-7, IA-8, IA-9; IB-1, IB-2, IB-3, IB-4, IB-5, IB-6; and IC-1, IC-2, IC-3, IC-4, IC-5, IC-6, summarized in Table 1a, are preferred. Each of the groups mentioned with respect to substituents in the table is further, independently of the combination in which it is mentioned, a particularly preferred embodiment of the substituent in question. [ka] [ka] [ka]

[0171] Table 1a Formulas IA-1, IA-2, IA-3, IA-4, IA-5, IA-6, IB-1, IB-2, IB-3, IB-4, IB-5, IB-6; Compounds of IC-1, IC-2, IC-3, IC-4, IC-5, IC-6; X for each individual compound 1 , X 2 , R 5 , R 6 , R 7 and R 8The meaning of each combination is that in each case, one row in Table B (compounds IA-1.1aB-1~IA-1.1aB-672, IA-2.1aB-1~IA-2.1aB-672, IA-3.1aB-1~IA-3.1aB-672, IA-4.1aB-1~IA-4.1aB-672, IA-5.1aB-1~IA-5.1aB-672, IA-6.1aB-1~IA-6.1aB-672, IA-6.1aB-1~IA-6.1aB-672, IA-8.1aB-1~IA-8.1aB-672, IA-9.1aB-1~IA-9.1aB-672; compound IB-1.1aB-1~IB-1.1aB-672, IB-2.1aB-1~IB-2.1aB-672, IB-3.1aB-1~IB-3.1aB-672, IB-4.1aB-1~IB-4.1aB- 672, IB-5.1aB-1~IB-5.1aB-672, IB-6.1aB-1~IB-6.1aB-672; Compound IC-1.1aB-1~IC This corresponds to IC-1.1aB-672, IC-2.1aB-1~IC-2.1aB-672, IC-3.1aB-1~IC-3.1aB-672, IC-4.1aB-1~IC-4.1aB-672, IC-5.1aB-1~IC-5.1aB-672, and IC-6.1aB-1~IC-6.1aB-672.

[0172] [Table 16]

[0173] [Table 17]

[0174] [Table 18]

[0175] [Table 19]

[0176] Table 20

[0177] Table 21

[0178] Table 22

[0179] Table 23

[0180] Table 24

[0181] Table 25

[0182] Table 26

[0183] Table 27

[0184] Table 28

[0185] Table 29

[0186] Table 30

[0187] Table 31

[0188] Table 32

[0189] Table 33

[0190] Table 34

[0191] Table 35

[0192] Table 36

[0193] Table 37

[0194] Table 38

[0195] Table 39

[0196] Table 40

[0197] [Table 41]

[0198] The compounds of the present invention can be prepared as shown in the following schemes, in which, unless otherwise specified, the definitions of each variable are as defined above for the compound of formula I. The compound of formula I can be prepared according to or in the same manner as described in the prior art. The synthesis utilizes starting materials that can be prepared by conventional procedures starting from commercially available or readily available compounds.

[0199] For example, compound I can be prepared in various oxidation states (Z=S, SO, or SO2), which are distinguished herein by being denoted as Ia (sulfide), Ib (sulfoxide), and Ic (sulfone). Compound Ia can be prepared by nucleophilic aromatic substitution and subsequent cyclization reaction of an aryl ketone (3) with an aminothiol represented by general formula (4) or their corresponding salt. These aminothiols can be prepared by many methods that are commercially available or expected to be known to those skilled in the art. The reaction is carried out in the presence of a suitable base (1-4 equivalents) such as Cs2CO3 or K2CO3 at ambient temperature or high temperature (40-60°C), similar to the procedure described in International Publication No. 2013 / 184734, 2013, A1, U.S. Patent No. 5371064, 1994, A, or Chem.Eur.J. 2015, 21(38), 13344-13356.

[0200] Compounds of formula I, represented as Ic in this specification, can be prepared by oxidizing dihydrobenzothiazepines represented by general formula Ia using hydrogen peroxide in combination with at least 2.0 equivalents of a suitable oxidizing agent, such as ammonium heptamolybdate, as a metal catalyst, as described in Catal.Commun.2009,10(14),1948-1951. Other methods, but not limited to, include other oxidizing agents such as peracids, hypervalent iodine reagents, halogenators, perhalic acids, nitric oxide, or metal oxides, as described in Phosphorus Sulfur Silicon Relat.Elem.2020,195,181-193.

[0201] Compounds of formula Ib can be prepared by oxidizing dihydrobenzothiazepine represented by general formula Ia using hydrogen peroxide in combination with an equimolar equivalent of a suitable oxidizing agent, such as ammonium heptamolybdate, as described in Dalton Trans. 2018, 47, 11882-11887, and a metal catalyst. Alternatively, compound Ic may be obtained from compound Ib by oxidation under these conditions described. [ka]

[0202] Aryl ketones (3) are commercially available or can be prepared by schemes such as oxidizing aryl alcohol 5 with manganese oxide, as described in Inorganica Chimica Acta (2012), 382, ​​72-78, International Publication No. 2000 / 038618, Specification CN107879989A, or Chinese Science Bulletin 2010, 55(25), 2817-2819. [ka]

[0203] The aryl alcohol (5) can be prepared by isopropylmagnesium chloride-mediated bromine / iodine-magnesium exchange of 7, followed by addition to a commercially available aldehyde represented by general formula (6). The reaction is preferably carried out at 0°C with equimolar amounts of iPrMgCl and aryl halide (7), as described in International Publication 2021 / 71821A1, J. Med. Chem., (2013), 56, 10158-10170, International Publication 2014 / 102233A1, or U.S. Patent Application Publication 2016 / 83401A1, and the intermediate is used with respect to aldehyde (6) in a ratio of 1.2 to 1.3:1. [ka]

[0204] Compound I and its compositions are particularly suitable as effective fungicides against a broad spectrum of plant pathogenic fungi, including soilborne pathogens, derived from the classes Plasmodiophoromycetes, Peronosporomycetes (also known as Oomycetes), Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, and Deuteromycetes (also known as Fungi imperfecti). They can be used for crop protection as foliar fungicides, seed coating fungicides, and soil fungicides.

[0205] Compound I and its compositions preferably include various cultivated plants, such as grains, such as wheat, rye, barley, rye grain, oats, or rice; beets, such as sugar beets or fodder beets; fruits, such as pome-like fruits (apples, pears, etc.), stone fruits (plums, peaches, almonds, cherries, etc.), or soft fruits also called berries (strawberries, raspberries, blackberries, currants, etc.); legumes, such as lentils, peas, alfalfa, or soybeans; oil plants, such as rapeseed, mustard, olives, sunflowers, coconuts, cocoa beans, castor oil plants, oil palms, peanuts, or soybeans; cucurbits, such as pumpkins, cucumbers, or melons; fiber plants, such as cotton, flax, cannabis, or horseradish; citrus fruits, such as oranges. It is useful for controlling plant pathogenic fungi in plants such as lemons, grapefruits, or mandarins; vegetables such as spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, melons, or bell peppers; plants of the Lauraceae family 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; climbing plants (grapes for eating and grape juice); hops; turf; snowbell (also known as stevia); natural rubber plants; or ornamental plants 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.

[0206] More preferably, compound I and its compositions are used to control fungi in 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, beans, or pumpkins.

[0207] The term “plant propagation material” is understood to refer to all reproductive parts of plants, such as seeds; as well as all plant materials capable of growth that can be used for plant propagation, such as cuttings and tubers (e.g., potatoes). Plant propagation material includes other parts of plants, including seeds, roots, fruits, tubers, bulbs, rhizomes, buds, shoots, and seedlings and young plants that are transplanted after germination or after emerging from the soil.

[0208] Preferably, treatment of plant propagation material with compound I and its compositions is used to control fungi in cereals such as wheat, rye, barley, and oats; rice, corn, cotton, and soybeans.

[0209] According to the present invention, all of the above-mentioned cultivated plants are understood to include, but are not limited to, all species, subspecies, varieties, cultivars and / or hybrids belonging to each cultivated plant, including, in particular, cereals such as wheat and barley, and winter and spring varieties of rapeseed, such as winter wheat, spring wheat, and winter barley.

[0210] Corn, also known as Indian corn or maize (Zea mays), includes all varieties such as feed corn and sweet corn. According to the present invention, all maize or subspecies and / or varieties of maize are included, in particular flower corn (Zea mays var. amylacea), popcorn (Zea mays var. everta), dent corn (Zea mays var. indentata), flint corn (Zea mays var. indurata), sweet corn (Zea mays var. saccharata and var. rugosa), waxy corn (Zea mays var. ceratina), amylomaize (high-amylose Zea mays varieties), pod corn or wildmaize (Zea mays var. tunicata), and variegated maize (Zea mays var. japonica).

[0211] Most soybean cultivars are classified into indestructible and finite growth types, although the wild ancestor of soybeans, Glycine soja, is indestructible (PNAS 2010, 107(19)8563-856). Indestructible growth types (maturity groups, MG 00 to MG 4.9) are characterized by continued plant growth after flowering begins, while finite soybean varieties (MG 5 to MG 8) are characterized by the fact that most of their plant growth is completed by the time flowering begins. According to the present invention, all soybean cultivars or varieties are included, and in particular, indestructible and finite cultivars or varieties are included.

[0212] The term "cultivated plant" is understood to include plants that are modified by mutagenesis or genetic engineering to confer new traits to plants or alter existing traits. Mutagenesis includes not only random mutagenesis using X-rays or mutagenic chemicals, but also targeted mutagenesis to induce mutations at specific loci in the plant genome. Targeted mutagenesis often uses oligonucleotides or proteins such as CRISPR / Cas, zinc finger nucleases, TALENs, or meganucleases. Genetic engineering typically uses recombinant DNA techniques to introduce modifications to the plant genome that are not readily obtainable in the natural environment through crossbreeding, mutagenesis, or natural recombination. Typically, one or more genes are incorporated into the plant genome to add a trait or improve or modify a trait. These incorporated genes are also called transgenes, and plants containing such transgenes are called transgenetic plants. The process of plant transformation usually involves several transformation events, each occurring at a different genomic locus in which the transgene is incorporated. Plants containing a specific transgene at a particular genomic locus are typically described as containing a specific “event” and referred to by the name of that event. Traits introduced or modified in plants include herbicide resistance, insect resistance, high yield, and tolerance to abiotic conditions such as drought.

[0213] Herbicide resistance can be induced using mutagenesis and genetic engineering. Plants resistant to acetolactate synthase (ALS) inhibitor herbicides through mutagenesis and breeding are available, for example, under the name Clearfield®. Herbicide resistance to oxynyl herbicides such as glyphosate, glufosinate, 2,4-D, dicamba, bromoxynil, and ioxinil, sulfonylurea herbicides, ALS inhibitors, and 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors such as isoxaflutol and mesotrione can be induced using transgenes.

[0214] Transgenes that confer herbicide resistance traits include: for resistance to glyphosate: cp4 epsps, epsps grg23ace5, mepsps, 2mepsps, gat4601, gat4621, goxv247; for resistance to glufosinate: pat and bar; for resistance to 2,4-D: aad-1, aad-12; for resistance to dicamba: dmo; for resistance to oxynyl herbicides: bxn; for resistance to sulfonylurea herbicides: zm-hra, csr1-2, gm-hra, S4-HrA; for resistance to ALS inhibitors: csr1-2; and for resistance to HPPD inhibitors: hppdPF, W336, avhppd-03.

[0215] Genetically modified maize events containing herbicide resistance genes include, but are not limited to, DAS40278, MON801, MON802, MON809, MON810, MON832, MON87411, MON87419, MON87427, MON88017, MON89034, NK603, GA21, MZHG0JG, HCEM485, VCO-Φ1981-5, 676, 678, 680, 33121, 4114, 59122, 98140, Bt10, Bt176, CBH-351, DBT418, DLL25, MS3, MS6, MZIR098, T25, TC1507, and TC6275. Genetically modified soybean events containing herbicide resistance genes include, but are not limited to, GTS40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21, A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS-81419-2, GU262, SYHTΦH2, W62, W98, FG72, and CV127. Genetically modified cotton vents containing herbicide resistance 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. Genetic transfection canola events containing herbicide resistance genes include, for example, MON88302, HCR-1, HCN10, HCN28, HCN92, MS1, MS8, PHY14, PHY23, PHY35, PHY36, RF1, RF2, and RF3, but do not exclude others.

[0216] The transgenes conferring insect resistance are preferably toxin genes and synthetic mutants of Bacillus species, such as cry1A, cry1Ab, cry1Ab-Ac, cry1Ac, cry1A.105, cry1F, cry1Fa2, cry2Ab2, cry2Ae, mcry3A, ecry3.1Ab, cry3Bb1, cry34Ab1, cry35Ab1, cry9C, vip3A(a), and vip3Aa20. Furthermore, plant-derived transgenes, such as genes encoding protease inhibitors like CpTI and pinII, can be used. A further approach involves using transgenes such as dvsnf7 to produce double-stranded RNA within plants.

[0217] Genetically modified maize events containing genes for insecticidal proteins or double-stranded RNA include, but are not limited to, Bt10, Bt11, Bt176, MON801, MON802, MON809, MON810, MON863, MON87411, MON88017, MON89034, 33121, 4114, 5307, 59122, TC1507, TC6275, CBH-351, MIR162, DBT418, and MZIR098. Genetically modified soybean events containing genes for insecticidal proteins include, but are not limited to, MON87701, MON87751, and DAS-81419. Genetically modified cotton events containing genes for insecticidal proteins include, but are not limited to, SGK321, MON531, MON757, MON1076, MON15985, 31707, 31803, 31807, 31808, 42317, BNLA-601, Event1, COT67B, COT102, T303-3, T304-40, GFM Cry1A, GK12, MLS9124, 281-24-236, 3006-210-23, GHB119, and SGK321.

[0218] By using the transgene athb17 (e.g., maize event MON87403) or bbx32 (e.g., soybean event MON87712), cultivated plants with increased yields have been produced.

[0219] Cultivated plants with modified oil content are produced using the following transgenes: gm-fad2-1, Pj.D6D, Nc.Fad3, fad2-1A, and fatb1-A (e.g., soybean event 260-05, MON87705, and MON87769).

[0220] Tolerance to abiotic conditions such as drought can be induced by using the transgenes cspB (maize event MON87460) and Hahb-4 (soybean event IND-ΦΦ41Φ-5).

[0221] Traits are often combined by combining genes in a transformation event or by combining different events during the breeding process, resulting in cultivated plants with accumulated traits. Preferred combinations of traits include combinations of herbicide resistance traits to different groups of herbicides, insect resistance to different types of insects, particularly lepidopteran and coleopteran insects, combinations of herbicide resistance with one or more types of insect resistance, combinations of herbicide resistance with yield increase, and combinations of herbicide resistance with tolerance to abiotic conditions.

[0222] Plants containing single or stacked traits, as well as the genes and events that confer these traits, are well known in this art. For example, detailed information on mutant or integrating genes and their respective events is available from the websites of the International Service for the Acquisition of Agri-biotech Applications (ISAAA) (http: / / www.isaaa.org / gmapprovaldatabase) and the Center for Environmental Risk Assessment (CERA) (http: / / cera-gmc.org / GMCropDatabase). Further information regarding specific events and methods for detecting them can be found in International Publication Nos. 01 / 031042, 01 / 041558, 01 / 041558, 02 / 036831, 11 / 153186, and 13 / 003558 for Canola Events MS1, MS8, RF3, GT73, MON88302, and KK179;For Wata Event MON1445, MON15985, MON531 (MON15985), LLCotton25, MON88913, COT102, 281-24-236, 3006-210-23, COT67B, GHB614, T304-40, GHB119, MON88701, and 81910, please refer to International Publication No. 02 / 034946, International Publication No. 02 / 100163, International Publication No. 02 / 100163, and International Publication No. 03 / 013224. Lett, International Publication No. 04 / 072235, International Publication No. 04 / 039986, International Publication No. 05 / 103266, International Publication No. 05 / 103266, International Publication No. 06 / 128573, International Publication No. 07 / 017186, International Publication No. 08 / 122406, International Publication No. 08 / 151780, International Publication No. 12 / 134808, International Publication No. 13 / 112527;For the corn events GA21, MON810, DLL25, TC1507, MON863, MIR604, LY038, MON88017, 3272, 59122, NK603, MIR162, MON89034, 98140, 32138, MON87460, 5307, 4114, MON87427, DAS40278, MON87411, 33121, MON87403, and MON87419, see International Publication No. 98 / 044140 and U.S. Patent Application Publication No. 02 / 102582. The document, US Patent Application Publication No. 03 / 126634 specification, International Publication No. 04 / 099447 brochure, International Publication No. 04 / 011601 brochure, International Publication No. 05 / 103301 brochure, International Publication No. 05 / 061720 brochure, International Publication No. 05 / 059103 brochure, International Publication No. 06 / 098952 brochure, International Publication No. 06 / 039376 brochure, US Patent Application Publication No. 2007 / 292854 specification, International Publication No. 07 / 142840 brochure, International Brochure No. 07 / 140256, International Publication No. 08 / 112019, International Publication No. 09 / 103049, International Publication No. 09 / 111263, International Publication No. 10 / 077816, International Publication No. 11 / 084621, International Publication No. 11 / 062904, International Publication No. 11 / 022469, International Publication No. 13 / 169923, International Publication No. 14 / 116854, International Publication No. 15 / 05 Pamphlet No. 3998, International Publication No. 15 / 142571; for Potato Events E12, F10, J3, J55, V11, X17, Y9, see International Publication Nos. 14 / 178910, International Publication Nos. 14 / 178913, International Publication Nos. 14 / 178941, International Publication Nos. 14 / 179276, International Publication Nos. 16 / 183445, International Publication Nos. 17 / 062831, International Publication Nos. 17 / 062825;For rice events LLRICE06, LLRICE601, and LLRICE62, see International Publication No. 00 / 026345, International Publication No. 00 / 026356, International Publication No. 00 / 026345; and soybean events H7-1, MON89788, A2704-12, A5547-127, DP305423, DP356043, M For ON87701, MON87769, CV127, MON87705, DAS68416-4, MON87708, MON87712, SYHT0H2, DAS81419, DAS81419×DAS44406-6, and MON87751, please refer to International Publication No. 04 / 074492, International Publication No. 06 / 130436, and International Publication No. 06 / 10 This can be found in pamphlets No. 8674, International Publication No. 06 / 108675, International Publication No. 08 / 054747, International Publication No. 08 / 002872, International Publication No. 09 / 064652, International Publication No. 09 / 102873, International Publication No. 10 / 080829, International Publication No. 10 / 037016, International Publication No. 11 / 066384, International Publication No. 11 / 034704, International Publication No. 12 / 051199, International Publication No. 12 / 082548, International Publication No. 13 / 016527, International Publication No. 13 / 016516, and International Publication No. 14 / 201235.

[0223] By applying Compound I and its compositions to cultivated plants, it is possible to induce plant-specific effects, including those involving specific transgenes or events. These effects may include changes in growth behavior or changes in resistance to biological or abiotic stressors. Such effects may include, in particular, increased yield, enhanced resistance or tolerance to insect pathogens, nematode pathogens, fungal pathogens, bacterial pathogens, mycoplasma pathogens, viral pathogens, or viroid pathogens, as well as early plant vigor, early or delayed maturation, cold tolerance or heat tolerance, and changes in the spectrum or content of amino acids or fatty acids.

[0224] Compound I and its compositions are particularly suitable for controlling the pathogenic factors of the following plant diseases: Albugo species (white rust disease) in ornamental plants, vegetables (e.g., A. candida) and sunflowers (e.g., A. tragopogonis); Alternaria species Alternaria spot disease (spp.) in vegetables (e.g., A. dauci or A. porri), rapeseed (A. brassicicola or brassicae), sugar beet (A. tenuis), fruit (e.g., A. grandis), rice, soybean, potato, and tomato (e.g., A. solani, A. grandis, or A. alternata), and wheat (e.g., A. triticina); Aphanomyces species in sugar beet and vegetables spp.); Ascochyta spp. in grains and vegetables, for example, A. tritici (anthracnose) in wheat and A. hordei in barley; Aureobasidium zeae (also known as Kapatiella zeae) in maize; Bipolaris and Drechslera spp. (Teleomorph: Cochliobolus spp.), for example, D. maydis or B. zeicola in maize; B. sorokiniana in grains; B. oryzae in rice and grass.oryzae; Blumeria (formerly known as Erysiphe) graminis (powdery mildew) in cereals (e.g., wheat or barley); Botrytis cinerea (teleomorph: Botryotinia fuckeliana): gray mold in fruits and berries (e.g., strawberries) and vegetables (e.g., lettuce, carrots, celery and cabbage); white spot leaf blight (B. squamosa) or gray rot (B. allii) in onions, rapeseed, ornamental plants (e.g., B. eliptica), climbing plants, forest plants and wheat; Bremia lactucae in lettuce lactucae (downy mildew); Ceratocystis species (synonym: Ophiostoma) (root rot or wilt disease) in deciduous and evergreen trees, for example, C. ulmi (Dutch elm disease) in elm; Cercospora species (Ceratocystis lactucae); (Cercospora spp.) (Cercospora leaf spot disease), which is found in maize (e.g., gray spot: C. zeae-maydis), rice, sugar beet (e.g., C. beticola), sugarcane, vegetables, coffee, soybeans (e.g., C. sojina or C. kikuchii) and rice; Cladobotryum (synonym: Dactylium) species (e.g., C. mycophilum) in mushrooms. (Formerly known as Dactylium dendroides, teleomorphs: Nectria albertinii, Nectria rosella, synonym: Hypomyces rosellus); Cladosporium species, including those in tomatoes (e.g., C. fulvum: leaf mold) and cereals, e.g., C. herbarum (black spot disease) in wheat; Claviceps purpurea in cereals. purpurea) (corn corn); Cochliobolus (anamorph: Helminthosporium of Bipolaris) species (leaf spot disease) in maize (C. carbonum), cereals (e.g., C. sativus, anamorph: B. sorokiniana) and rice (e.g., C. miyabeanus, anamorph: H. oryzae); Colletotrichum (teleomorph: Glomerella) species (anthrax) in cotton (e.g., C. gossypii), maize (e.g. For example, in C. graminicola (anthracnose root rot), soft fruits, potatoes (e.g., C. coccodes: black spot), legumes (e.g., C. lindemuthianum), soybeans (e.g., C. truncatum or C. gloeosporioides), vegetables (e.g., C. lagenarium or C. capsici), fruits (e.g., C. acutatum), coffee (e.g., C. coffeeum or C. kahawae), and in C. gloeosporioides in various crops.gloeosporioides); Corticium spp. in rice, e.g. C. sasakii (sheath blight); Corynespora cassiicola in soybeans, cotton and ornamental plants (leaf spot); Cycloconium spp., e.g. C. oleaginum in olives; Cylindrocarpon spp. (e.g., fruit tree ulcer or weakening of young vines, teleomorph: Nectria or Neonectria spp.)), fruit trees, vines (e.g., C. liriodendri, teleomorph: Neonectria liriodendri) liriodendri (black foot disease) and in ornamental plants; Dematophora (Teleomorph: Roselinia) and Necatrix (root and stem rot) in soybeans; Diaporthe in soybeans spp.), for example, D. phaseolorum (seedling blight); Dreshlera (synonym: Helminthosporium, teleomorph: Pyrenophora) species, in maize, cereals, for example, barley (e.g., D. teres, net spot disease) and wheat (e.g., D. tritici-repentis: yellowish-brown spot disease), rice, and turfgrass; Formitiporia (synonym: Phellinus) punctata, F. mejiteranea (F.Esca disease (canker, apoplexy) in climbing plants caused by mediterranea), Phaeomoniella chlamydospora (formerly known as Phaeoacremonium chlamydosporum), Phaeoacremonium aleophilum, and / or Botryosphaeria obtusa; Elsinoe spp. in pear-shaped fruits (E. piri), soft fruits (E. veneta: anthracnose) and climbing plants (E. ampelina: anthracnose); Entyloma oryzae in rice oryzae (leaf sooty mold); Epicoccum spp. (black mold) in wheat; Erysiphe spp. (powdery mildew) in sugar beet (E. betae), vegetables (e.g., E. pisi), cucurbits (e.g., E. cichoracearum), cabbage, rapeseed (e.g., E. cruciferarum); Eutypa lata (eutypa ulcer or canker, anamorph: Cytosporina lata, synonym: Libertella brepalis) in fruit trees, climbing plants and ornamental trees; Eutypa lata (eutypa ulcer or canker, anamorph: Cytosporina lata, synonym: Libertella brepalis) in fruit trees, climbing plants and ornamental trees. blepharis); Exserohilum (synonym: Helminthosporium) species in maize (e.g., E. turcicum); Fusarium (teleomorph: Gibberella) species in various plants (wilt, root rot or stem rot), for example, F. graminearum or F. culmorum in cereals (e.g., wheat or barley) (root rot, scab or head blight); F. oxysporum in tomatoes (F.F. oxysporum), F. solani (soybean-specific type (f.sp.glycines), current synonym: F. virguliforme), F. tucumaniae, and F. brasiliense, which cause acute wilt disease in soybeans, as well as F. verticillioides in maize; Gaeumannomyces graminis (ground rot) in cereals (e.g., wheat or barley) and maize; Gibberella species (Gibberella spp.) in cereals (e.g., G. zeae) and rice (e.g., G. fujikuroi: bakanae disease); and Glomerella singurata in climbing plants, pears, and other plants. G. cingulata) and G. gossypii in cotton; Grainstaining complex in rice; Guignardia bidwellii (black spot disease) in climbing plants; Gymnosporangium spp. in Rosaceae plants and junipers, e.g., G. sabinae (rust disease) in pears; Helminthosporium spp. (synonym: Drechslera, teleomorph: Cochliobolus) in maize, cereals, potatoes and rice; Hemileia spp. in coffee, e.g., H. bustatrix (H.vastatrix (coffee rust); Isariopsis clavispora (synonym: Cladosporium vitis) in climbing plants; Macrophomina phaseolina (synonym: phaseoli) (root rot and stem rot) in soybeans and cotton; Microdochium (synonym: Fusarium nivale) (pink snow mold) in cereals (e.g., wheat or barley); Microsphaera diffusa (powdery mildew) in soybeans; Monilinia species in berries and other Rosaceae plants spp.), for example, M. laxa, M. fructicola, and M. fructigena (synonym: Monilia spp.: flower blight and branch blight, brown rot); Mycosphaerella spp. in grains, bananas, soft fruits and peanuts, for example, M. graminicola in wheat (anamorph: Zymoseptoria tritici, formerly known as Septoria tritici: Septoria leaf spot) or M. fijiensis in banana (synonym: Pseudocercospora fijiensis) fijiensis: black sigatoka disease) and M. musicola, M. arachidicola in peanuts (synonym: M. arachidis or Cercospora arachidis), M. berkeleyi, M. pisi in peas, and M. brassiciola in Brassicaceae plants; Peronospora spp. (downy mildew), such as cabbage (e.g., P. brassicae), rapeseed (e.g., P. parasitica (P.In *P. parasitica*, onions (e.g., *P. destroyer*), tobacco (*P. tabacina*), and soybeans (e.g., *P. manshurica*); in soybeans, *Phakopsora pachyrhizi* and *P. meibomiae* (soybean rust); in *Phialophora* species, for example, climbing plants (e.g., *P. tracheiphila* and *P. tetraspora*) and soybeans (e.g., *P. gregata*: stem rot); in rapeseed and cabbage, *Phoma lingam* (synonym: *Leptosphaeria biglobosa*). P. biglobosa) and L. maculans (root and stem rot), P. betae in sugar beets (root rot, leaf spot and seedling blight), and P. zeae-maydis (synonym: Phyllostica zeae) in maize; Phomopsis species (Phomopsis spp.), including sunflowers, climbing plants (e.g., P. viticola). ticola: leaf spot disease) and in soybeans (e.g., stem rot: P. phaseoli, teleomorph: Diaporthe phaseolorum); Physoderma maydis (leaf spot disease) in maize; Phytophthora species Plasmodiophora brassicae (club root disease) in cabbage, rapeseed, radish and other plants; Plasmopara species (Plasmopara) P. viticola (grapevine downy mildew), for example, in climbing plants and P. halstedii in sunflowers; P. podosphaera spp. (powdery mildew), found in Rosaceae plants, hops, pears and soft fruits (e.g., P. leucotricha in apples) and Cucurbitaceae plants (P. xanthii); Polymyxa spp., for example, in cereals such as barley and wheat (P. graminis) and sugar beets (P. betae), and the viral diseases transmitted by them; Pseudocercosporella herpotrichoides in cereals, for example, wheat or barley. herpotrichoides) (Synonyms: Oculimacula yallundae, O. akformis)acuformis): eye spot disease, teleomorph: Tapesia yallundae; Pseudoperonospora (downy mildew) in various plants, e.g., P. cubensis in cucurbits or P. humili in hops; Pseudopezicula tracheiphila (red fireworks or rotbrenner, anamorph: phialophora) in climbing plants; Puccinia species in various plants P. triticina (brown rust or leaf rust), P. striiformis (striped rust or yellow rust), P. hordei (dwarf rust), P. graminis (stem rust or black rust) or P. recondita (brown rust or leaf rust) in grains such as wheat, barley or rye; P. kuehnii (orange rust) in sugarcane; and P. asparagi in asparagus; and Pyrenopeziza in rapeseed. Pyricularia spp.), for example, P. brassicae; Pyrenophora (anamorph: Drechslera) · tritici-repentis (yellowish-brown spot disease) in wheat or P. teres (net-like spot disease) in barley; Pyricularia spp., for example, P. oryzae (teleomorph: Magnaporthe grisea: rice blight) in rice and P. grisea in grass and cereals; Pythium species in grass, rice, maize, wheat, cotton, rapeseed, sunflower, soybean, sugar beet, vegetables and various other plants. (spp.) (Seedling blight) (For example, P. ultimum or P. afanidermatsum (P.P. oligandrum in aphanidermatum and mushrooms; Ramularia species (Ramularia spp.), such as R. collo-cygni (Ramularia leaf spot disease, physiological leaf spot disease) in barley, R. areola (Teleomorph: Mycosphaerella areola) in cotton and R. beticola in sugar beet; Rhizoctonia species in cotton, rice, potato, grass, maize, rapeseed, potato, sugar beet, vegetables and various other plants. (spp.), for example, R. solani (root and stem rot) in soybeans, R. solani (sheath blight) in rice, or R. cerealis (Rhizoctonia spring blight) in wheat or barley; Rhizopus stolonifer (black mold, soft rot) in strawberries, carrots, cabbage, climbing plants and tomatoes; Rhynchosporium secalis and R. commune (burn disease) in barley, rye and rye; Sarocladium oryzae and S. attenuatum (coat rot) in rice; Sclerotinia species (spp.) (stem rot or white mold disease), which is found in vegetables (S. minor and S. sclerotiorum) and crops, such as rapeseed, sunflowers (e.g., S. sclerotiorum) and soybeans; S. rolfsii (synonym: Athelia rolfsii) in soybeans, peanuts, vegetables, corn, grains and ornamental plants; Septoria species (Septoria spp.) in various plants, such as S. glycines (brown spot disease) in soybeans, S. tritici (synonym: Zymoseptoria tritici, Septoria spot disease) in wheat, and S.(Synonym: Stagonospora) nodorum (Stagonospora spot disease); Uncinula (Synonym: Erysiphe) necator (Powdery mildew, anamorph: Oidium tuckeri) in climbing plants; Setosphaeria spp. (Black leaf blight) in maize (e.g., S. turcicum, synonym: Helminthosporium turcicum), and in turfgrass; Sphacelotheca spp. (Sooty mold) in maize (e.g., S. reiliana, synonym: Ustilago reiliana) reiliana (smut), in sorghum and sugarcane; Sphaerotheca fuliginea in cucurbitaceae plants, synonym: Podosphaera xanthii (powdery mildew); Spongospora subterranea (floury crusting) in potatoes and the viral diseases transmitted by it; Stagonospora species in cereals, such as S. nodorum in wheat (Stagonospora spot disease, teleomorph: Leptosphaeria [synonym: Phaeosphaeria] nodorum, synonym: Septoria nodorum]); Synchytrium endobioticum in potatoes T. endobioticum) (potato wart disease); Taphrina spp., e.g., T. deformans (leaf curl disease) in peaches, and T. pruni (pocket plum) in plums; Thielaviopsis spp. (black root rot) in tobacco, pears, vegetables, soybeans, and cotton, e.g., T. basicola (T.Tilletia species (T. basicola) (synonym: Chalara elegans); Tilletia species in cereals (smut or wheat smut), for example, T. tritici (synonym: T. caries, net smut) and T. controversa (dwarf smut) in wheat; Trichoderma harzianum in mushrooms; Typhula incarnata (gray snow mold) in barley or wheat; Urocystis species, for example, U. occulta (sooty mold) in rye; Uromyces species in vegetables Rust disease (spp.), for example, in legumes (e.g., U. appendiculatus, synonym: U. phaseoli), sugar beets (e.g., U. betae or U. beticola), and in leguminous plants (e.g., U. vignae, U. pisi, U. viciae-fabae, and U. fabae); Ustilago species spp.) (naked smut), in cereals (e.g., U. nuda and U. avaenae), maize (e.g., U. maydis: maize sooty mold) and sugarcane; Venturia spp. (black spot), in apples (e.g., V. inaequalis) and pears; and Verticillium spp. (damping-off), in various plants such as fruit and ornamental plants, vines, soft fruits, vegetables and crops, e.g., V. longisporum in rapeseed, V. dahliae in strawberries, rapeseed, potatoes and tomatoes, and V. fungikola in mushrooms.*fungicola*; the wheat leaf blight fungus (Zymoseptoria tritici) in cereals.

[0225] Compound I and its compositions are particularly suitable for controlling the pathogenic factors of the following plant diseases: rust in soybeans and cereals (e.g., Phakopsora pachyrhizi and P. meibomiae in soybeans; Puccinia tritici and P. striiformis in wheat); fungal diseases in specialty crops, soybeans, rapeseed and sunflowers (e.g., Botrytis cinerea in strawberries and climbing plants; Sclerotinia sclerotiorum, S. minor and S. rolfsii in rapeseed, sunflowers and soybeans); and Fusarium disease in cereals (e.g., Fusarium crumorum in wheat). F. culmorum) and F. graminearum); downy mildew in specialty crops (e.g., Plasmopara viticola in climbing plants, Phytophthora infestans in potatoes); powdery mildew in specialty crops and cereals (e.g., Uncinula necator in climbing plants, Erysiphe spp. in various specialty crops, Blumeria graminis in cereals); and leaf spot diseases in cereals, soybeans and maize (e.g., Septoria tritici and S. nodorum in cereals, S. glycines in soybeans, Cercospora spp. in maize and soybeans).

[0226] According to one embodiment, compounds IA-1.1aB-1 to IA-1.1aB-180 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0227] According to one embodiment, compounds IA-2.1aB-1 to IA-2.1aB-180 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0228] According to one embodiment, compounds IA-3.1aB-1 to IA-3.1aB-180 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0229] According to one embodiment, compounds IA-4.1aB-1 to IA-4.1aB-180 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0230] According to one embodiment, compounds IA-5.1aB-1 to IA-5.1aB-180 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0231] According to one embodiment, compounds IA-6.1aB-1 to IA-6.1aB-180 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0232] According to one embodiment, compounds IA-1.2aB-1 to IA-1.2aB-180 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0233] According to one embodiment, compounds IA-2.2aB-1 to IA-2.2aB-180 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0234] According to one embodiment, compounds IA-3.2aB-1 to IA-3.2aB-180 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0235] According to one embodiment, compounds IA-4.2aB-1 to IA-4.2aB-180 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0236] According to one embodiment, compounds IA-5.2aB-1 to IA-5.2aB-180 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0237] According to one embodiment, compounds IA-6.2aB-1 to IA-6.2aB-180 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0238] According to one embodiment, compounds IA-1.3aB-1 to IA-1.3aB-180 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0239] According to one embodiment, compounds IA-2.3aB-1 to IA-2.3aB-180 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0240] According to one embodiment, compounds IA-3.3aB-1 to IA-3.3aB-180 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0241] According to one embodiment, compounds IA-4.3aB-1 to IA-4.3aB-180 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0242] According to one embodiment, compounds IA-5.3aB-1 to IA-5.3aB-180 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0243] According to one embodiment, compounds IA-6.3aB-1 to IA-6.3aB-180 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0244] According to one embodiment, compounds IA-1.4aB-1 to IA-1.4aB-180 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0245] According to one embodiment, compounds IA-2.4aB-1 to IA-2.4aB-180 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0246] According to one embodiment, compounds IA-3.4aB-1 to IA-3.4aB-180 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0247] According to one embodiment, compounds IA-4.4aB-1 to IA-4.4aB-180 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0248] According to one embodiment, compounds IA-5.4aB-1 to IA-5.4aB-180 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0249] According to one embodiment, compounds IA-6.4aB-1 to IA-6.4aB-180 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0250] According to one embodiment, compounds IA-1.5aB-1 to IA-1.5aB-180 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0251] According to one embodiment, compounds IA-2.5aB-1 to IA-2.5aB-180 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0252] According to one embodiment, compounds IA-3.5aB-1 to IA-3.5aB-180 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0253] According to one embodiment, compounds IA-4.5aB-1 to IA-4.5aB-180 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0254] According to one embodiment, compounds IA-5.5aB-1 to IA-5.5aB-180 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0255] According to one embodiment, compounds IA-6.5aB-1 to IA-6.5aB-180 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0256] According to one embodiment, compounds IA-1.6aB-1 to IA-1.6aB-180 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0257] According to one embodiment, compounds IA-2.6aB-1 to IA-2.6aB-180 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0258] According to one embodiment, compounds IA-3.6aB-1 to IA-3.6aB-180 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0259] According to one embodiment, compounds IA-4.6aB-1 to IA-4.6aB-180 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0260] According to one embodiment, compounds IA-5.6aB-1 to IA-5.6aB-180 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0261] According to one embodiment, compounds IA-6.6aB-1 to IA-6.6aB-180 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0262] According to one embodiment, compounds IA-1.7aB-1 to IA-1.7aB-180 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0263] According to one embodiment, compounds IA-2.7aB-1 to IA-2.7aB-180 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0264] According to one embodiment, compounds IA-3.7aB-1 to IA-3.7aB-180 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0265] According to one embodiment, compounds IA-4.7aB-1 to IA-4.7aB-180 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0266] According to one embodiment, compounds IA-5.7aB-1 to IA-5.7aB-180 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0267] According to one embodiment, compounds IA-6.7aB-1 to IA-6.7aB-180 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0268] According to one embodiment, compounds Ex-1 to Ex-92 are particularly suitable for controlling the pathogenic factors of plant diseases listed in Z.

[0269] List Z: Albugo species (white rust disease) in ornamental plants, vegetables (e.g., A. candida) and sunflowers (e.g., A. tragopogonis); Alternaria species Alternaria spot disease (spp.) in vegetables (e.g., A. dauci or A. porri), rapeseed (A. brassicicola or brassicae), sugar beet (A. tenuis), fruit (e.g., A. grandis), rice, soybean, potato, and tomato (e.g., A. solani, A. grandis, or A. alternata), and wheat (e.g., A. triticina); Aphanomyces species in sugar beet and vegetables spp.); Ascochyta spp. in grains and vegetables, for example, A. tritici (anthracnose) in wheat and A. hordei in barley; Aureobasidium zeae (also known as Kapatiella zeae) in maize; Bipolaris and Drechslera spp. (Teleomorph: Cochliobolus spp.), for example, D. maydis or B. zeicola in maize; B. sorokiniana in grains; B. oryzae in rice and grass.oryzae; Blumeria (formerly known as Erysiphe) graminis (powdery mildew) in cereals (e.g., wheat or barley); Botrytis cinerea (teleomorph: Botryotinia fuckeliana): gray mold in fruits and berries (e.g., strawberries) and vegetables (e.g., lettuce, carrots, celery and cabbage); white spot leaf blight (B. squamosa) or gray rot (B. allii) in onions, rapeseed, ornamental plants (e.g., B. eliptica), climbing plants, forest plants and wheat; Bremia lactucae in lettuce lactucae (downy mildew); Ceratocystis species (synonym: Ophiostoma) (root rot or wilt disease) in deciduous and evergreen trees, for example, C. ulmi (Dutch elm disease) in elm; Cercospora species (Ceratocystis lactucae); (spp.) (Cercospora leaf spot disease), which is found in corn (e.g., gray spot: C. zeae-maydis), rice, sugar beet (e.g., C. beticola), sugarcane, vegetables, coffee, soybeans (e.g., C. sojina or C. kikuchii) and rice; Cladobotryum (synonym: Dactylium) species in mushrooms (e.g., C. mycophilum (formerly Dactylium dendroide, teleomorph: Nectria albertinii, Nectria rosella, synonym: Hypomyces rosella) Cladosporium species (C. rosellus)); Cladosporium spp., which are found in tomatoes (e.g., C. fulvum: leaf mold) and cereals, for example, C. herbarum (C.herbarum) (black spot disease); Claviceps purpurea in cereals purpurea) (corn rot); Cochliobolus (anamorph: Helminthosporium of Bipolaris) species (leaf spot disease) in maize (C. carbonum), cereals (e.g., C. sativus, anamorph: B. sorokiniana) and rice (e.g., C. miyabeanus, anamorph: H. oryzae); Colletotrichum (teleomorph: Glomerella) species (anthracnose) in cotton (e.g., C. gossypii) and maize (e.g., C. gramini) Corticium in various crops; Corticium species in rice; Corticium spp.), e.g., C. sasakii (sheath blight); Corynespora cassiicola (leaf spot) in soybeans, cotton and ornamental plants; Cycloconium spp., e.g., C. oleaginum in olives; Cylindrocarpon spp.)(for example, fruit tree ulcer disease or weakness of young climbing plants, teleomorph: Nectria or Neonectria spp.) in fruit trees, climbing plants (for example, C. liriodendri, teleomorph: Neonectria liriodendri: black foot disease) and ornamental plants; Dematophora (teleomorph: Roselinia) necatrix (root and stem rot) in soybeans; Diaporthe in soybeans spp.), for example, D. phaseolorum (seedling blight); Dreshlera (synonym: Helminthosporium, teleomorph: Pyrenophora) species, found in maize, cereals, such as barley (e.g., D. teres, net-like spot disease) and wheat (e.g., D. tritici-repentis: yellow-brown spot disease), rice, and turfgrass; Formitiporia (synonym: Phellinus) punctata, F. mediterranea, Phaeomoniella chlamydospora Esca disease (canker, apoplexy) in climbing plants caused by chlamydospora (formerly known as Phaeoacremonium chlamydosporum), Phaeoacremonium aleophilum and / or Botryosphaeria obtusa; Elsinoe spp., including pear-shaped fruits (E. piri), soft fruits (E. veneta: anthracnose) and climbing plants (E. amperina (E.ampelina: anthracnose; Entyloma oryzae (sooty mold) in rice; Epicoccum spp. (black mold) in wheat; Erysiphe spp. (powdery mildew), in sugar beet (E. betae), vegetables (e.g., E. pisi), cucurbitaceous plants (e.g., E. cichoracearum), cabbage, rapeseed (e.g., E. cruciferarum); Eutypa lata (Eutypa ulcer or canker, anamorph: Cytosporina lata) in fruit trees, vines and ornamental trees. lata), synonym: Libertella blepharis; Exserohilum (synonym: Helminthosporium) species in maize (e.g., E. turcicum); Fusarium (teleomorph: Gibberella) species in various plants (wilting, root rot or stem rot), for example, F. graminearum or F. culmorum in cereals (e.g., wheat or barley) (root rot, red mold (scab or head rot)). F. oxysporum in tomatoes, F. solani (soybean-specific type (f.sp.glycines), current synonym: F. virguliforme), F. tucumaniae, and F. brasiliense in soybeans, which cause acute wilt disease, as well as F. verticillioides in maize; Gaeumannomyces graminis (root rot) in cereals (e.g., wheat or barley) and maize; Gibberella species (Gibberella spp.), including cereals (e.g., G. zeae) and rice (e.g., G. fusiliense).fujikuroi: (in the case of bakanae disease); Glomerella cingulata in climbing plants, pears and other plants, and G. gossypii in cotton; Grainstaining complex in rice; Guignardia bidwellii (black spot disease) in climbing plants; Gymnosporangium spp. in Rosaceae plants and junipers, for example, G. sabinae (rust disease) in European pears; Helminthosporium spp. (synonym: Drechslera, teleomorph: Cochliobolus) in maize, cereals, potatoes and rice; Hemileia in coffee (spp.), for example, H. vastatrix (coffee). - Rust disease; Isariopsis clavispora (synonym: Cladosporium vitis) in climbing plants; Macrophomina phaseolina (synonym: phaseoli) (root rot and stem rot) in soybeans and cotton; Microdochium (synonym: Fusarium nivale) (pink snow mold) in cereals (e.g., wheat or barley); Microsphaera diffusa (powdery mildew) in soybeans; Monilinia species in berries and other Rosaceae plants spp.), for example, M. laxa, M. fructicola, and M. fructigena (synonym: Monilia spp.: flower blight and branch blight, brown rot); Mycosphaerella spp. in grains, bananas, soft fruits and peanuts, for example, M. graminicola in wheat (anamorph: Zymoseptoria tritici, formerly known as Septoria tritici: Septoria leaf spot) or M. fijiensis in banana (synonym: Pseudocercospora fijiensis) fijiensis: black sigatoka disease) and M. musicola, M. arachidicola in peanuts (synonym: M. arachidis or Cercospora arachidis), M. berkeleyi, M. pisi in peas, and M. brassiciola in Brassicaceae plants; Peronospora spp. (downy mildew), such as cabbage (e.g., P. brassicae), rapeseed (e.g., P. parasitica (P.In *P. parasitica*, onions (e.g., *P. destroyer*), tobacco (*P. tabacina*), and soybeans (e.g., *P. manshurica*); in soybeans, *Phakopsora pachyrhizi* and *P. meibomiae* (soybean rust); in *Phialophora* species, for example, climbing plants (e.g., *P. tracheiphila* and *P. tetraspora*) and soybeans (e.g., *P. gregata*: stem rot); in rapeseed and cabbage, *Phoma lingam* (synonym: *Leptosphaeria biglobosa*). P. biglobosa and L. maculans (root and stem rot), P. betae in sugar beets (root rot, leaf spot, and seedling blight), and P. zeae-maydis (synonym: Phyllostica zeae) in maize; Phomopsis species in sunflowers, climbing plants (e.g., P. viticola: leaf spot), and soybeans (e.g., stem rot: P. phaseoli, teleomorph: Diaporthe phaseolorum); Physoderma maydis (leaf spot) in maize; Phytophthora species (spp.) (yellowing disease, roots, leaves, fruits or stem roots), affecting various plants, such as paprika and cucurbitaceous plants (e.g., P. capsici), soybeans (e.g., P. megasperma, synonym: P. sojae), potatoes and tomatoes (e.g., P. infantans: leaf blight), and deciduous trees (e.g., P. lamorum (P.Ramorum: In the case of sudden death of oak; Plasmodiophora brassicae (club root disease) in cabbage, rapeseed, radish and other plants; Plasmopara species, e.g., P. viticola (grape downy mildew) in climbing plants and P. halstedii in sunflowers; Podosphaera species (powdery mildew) in Rosaceae plants, hops, pears and soft fruits (e.g., P. leucotricha in apples) and Cucurbitaceae plants (P. xanthii); Polymyxa species (spp.) such as those found in cereals (P. graminis) and sugar beets (P. betae), and the viral diseases transmitted thereby; Pseudocercosporella herpotrichoides (synonyms: Oculimacula yallundae, O. acuformis: eye spot disease, teleomorph: Tapesia yallundae) in cereals, such as wheat or barley; Pseudoperonospora (downy mildew) in various plants, such as P. cubensis in cucurbits or P. humili in hops; Pseudopezicula tracheiphylla in climbing plants P. tracheiphila) (red fireworks or rotbrenner, anamorph: phialophora); Puccinia spp. (rust) in various plants, for example, P. triticina (brown rust or leaf rust), P. striiformis (striped rust or yellow rust), P. hordei (dwarf rust), P. graminis (P.P. graminis (stem rust or black rust) or P. recondita (brown rust or leaf rust), P. kuehnii (orange rust) in sugarcane and P. asparagi in asparagus; Pyrenopeziza spp. in rapeseed, e.g., P. brassicae; Pyrenophora (anamorph: Drechslera) · tritici-repentis (yellowish-brown spot) in wheat or P. teres (net spot) in barley; Pyricularia P. spp.), for example, P. oryzae (teleomorph: Magnaporthe grisea: rice blight) in rice and P. grisea in grass and cereals; Pythium spp. (seedling blight) in grass, rice, maize, wheat, cotton, rapeseed, sunflower, soybean, sugar beet, vegetables and various other plants (e.g., P. ultimum or P. aphanidermatum) and P. oligandrum in mushrooms; Ramularia species Rhizoctonia spp.), for example, R. collo-cygni (ramularia leaf spot, physiological leaf spot) in barley, R. areola (teleomorph: Mycosphaerella areola) in cotton and R. beticola in sugar beet; Rhizoctonia spp. in cotton, rice, potato, grass, maize, rapeseed, potato, sugar beet, vegetables and various other plants, for example, R. solani (root and stem rot) in soybeans, R. solani (sheath blight) in rice or R. cerealis (R.Rhizoctonia cerealis (spring blight); Rhizopus stolonifer (black mold, soft rot) in strawberries, carrots, cabbage, climbing plants and tomatoes; Rhynchosporium secalis and R. commune (burn disease) in barley, rye and rye; Sarocladium oryzae and S. attenuatum (coat rot) in rice; Sclerotinia species (spp.) (stem rot or white mold) in vegetables (S. minor and S. sclerotiorum) and crops, such as rapeseed, sunflowers (e.g., S. sclerotiorum) and soybeans; S. rolfsii (synonym: Athelia rolfsii) in soybeans, peanuts, vegetables, maize, grains and ornamental plants; Septoria species (spp.) in various plants, such as S. glycines (brown spot) in soybeans and S. tritici (synonym: Zymoseptoria) in wheat. S. tritici), Septoria spot), and S. (synonym: Stagonospora) nodorum (Stagonospora spot) in cereals; Uncinula (synonym: Erysiphe) necator (powdery mildew, anamorph: Oidium tuckeri) in climbing plants; Setosphaeria spp. (black leaf blight) in maize (e.g., S. turcicum, synonym: Helminthosporium turcicum), and those in turfgrass; Sphacelotheca spp. (sooty mold) in maize (e.g., S. leiliana (S.Sphaerotheca fuliginea, synonym: Ustilago reiliana (black smut), found in sorghum and sugarcane; Sphaerotheca fuliginea, synonym: Podosphaera xanthii (powdery mildew), found in cucurbitaceae plants; Spongospora subterranea (powdery crusting) in potatoes and the viral diseases it causes; Stagonospora species in cereals, such as S. nodorum in wheat (Stagonospora spot, tere). Omorphs: Leptosphaeria (synonym: Phaeosphaeria) nodorum, Septoria nodorum); Synchytrium endobioticum (potato wart) in potatoes; Taphrina species, e.g., T. deformans (leaf curl) in peaches, and T. pruni (pocket plum) in plums; Thielaviopsis species (black root rot) in tobacco, pears, vegetables, soybeans, and cotton, e.g., T. basicola (synonym: Chalara elegans); Tilletia species in cereals (spp.) (smut or wheat smut), for example, T. tritici (synonym: T. caries, net smut) and T. controversa (dwarf smut) in wheat; Trichoderma harzianum in mushrooms; Typhula incarnata (gray snow mold) in barley or wheat; Urocystis species (spp.), for example, U. occulta (sooty stripe mold) in rye; Uromyces species in vegetables Rust disease (spp.), for example, in legumes (e.g., U. appendiculatus, synonym: U. phaseoli), sugar beets (e.g., U. betae or U. beticola), and leguminous plants (e.g., U. vignae, U. pisi, U. viciae-fabae, and U. fabae); Ustilago spp. (naked smut), which is found in cereals (e.g., U. nuda and U. avaenae), maize (e.g., U.Maydis (U. maydis): maize sooty mold and sugarcane; Venturia spp. (black spot disease), in apples (e.g., V. inaequalis) and pears; and Verticillium spp. (damping-off disease) in various plants, such as fruit and ornamental plants, vines, soft fruits, vegetables and crops, such as V. longisporum in rapeseed, V. dahliae in strawberries, rapeseed, potatoes and tomatoes, and V. fungicola in mushrooms; and Zymoseptoria tritici, the wheat leaf spot fungus in cereals.

[0270] Compound I and its compositions are also suitable for controlling harmful microorganisms in the protection of stored products or harvested goods and in the protection of materials, respectively.

[0271] The term “storage products or harvested products” is understood to mean natural substances of plant or animal origin and their processed forms that require long-term protection. Plant-derived storage products, such as stems, leaves, tubers, seeds, fruits, or grains, can be protected in their freshly harvested state or in processed forms such as pre-drying, wetting, crushing, pulverizing, pressing, or roasting, processes also known as post-harvest treatments. The definition of storage products also includes wood, which may be in the form of roughly processed wood such as building timber, utility poles, and fences, or in the form of finished products such as furniture and wooden articles. Animal-derived storage products include hides, leather, fur, and hair. Preferably, “storage products” is understood to mean natural substances of plant origin and their processed forms, more preferably fruits and their processed forms, such as pears, stone fruits, soft fruits, and citrus fruits and their processed forms, and the application of Compound I and its compositions can also prevent adverse effects such as decay, discoloration, or mold.

[0272] The term "protection of materials" is understood to mean the protection of technical and abiotic materials such as adhesives, glues, wood, paper, cardboard, textiles, leather, paint dispersions, plastics, coolants and lubricants, fibers, or cloths from intrusion and destruction by harmful microorganisms such as fungi and bacteria.

[0273] When used for the protection of materials or stored products, the amount of active substance applied depends on the type of application area and the desired effect. The amount conventionally applied for the protection of materials is 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of the active substance per cubic meter of treated material.

[0274] Compound I and its compositions can each 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 place where plants are growing or intend to grow, with effective amounts of Compound I and its compositions.

[0275] The term “plant health” is understood to describe the state of a plant and / or its products, determined individually or in combination with several indicators, such as yield (e.g., increased biomass and / or increased content of beneficial components), plant vitality (e.g., improved plant growth and / or leaf greening ("greening effect")), quality (e.g., improved content or composition of specific components), and tolerance to abiotic and / or biological stress. The above-mentioned indicators of plant health may be interdependent or attributable to each other.

[0276] Compound I is used either as is or in composition by treating plant propagation materials such as fungi, plants, and seeds; or soil, surfaces, materials, or rooms that need protection from fungal infection, with an effective amount of the active substance. Application can be carried out both before and after fungal infection of plant propagation materials such as plants, seeds, and soil, surfaces, materials, or rooms.

[0277] The pesticide composition contains a fungicidal effective amount of compound I. The term "fungicidal effective amount" means an amount of composition or compound I that is sufficient to control harmful fungi in cultivated plants or to protect stored products, harvested products, or materials, and that does not cause substantial damage to the treated plants, treated stored products, harvested products, or materials. Such an amount may vary widely and depends on various factors such as the fungal species to be controlled, the cultivated plants, stored products, harvested products, or materials being treated, climatic conditions, and the specific compound I used.

[0278] Plant propagation material may be treated preventively with compound I in its pure form or with a composition containing at least one compound I at the time of planting or transplanting, or either beforehand.

[0279] When used for plant protection, the application rate of the active substance is 0.001 to 2 kg per hectare, preferably 0.005 to 2 kg per hectare, more preferably 0.05 to 0.9 kg per hectare, and particularly 0.1 to 0.75 kg per hectare, depending on the type of effect desired.

[0280] For example, in the treatment of plant propagation materials such as seeds by powdering, coating, or drenching, an amount of active substance is generally required of 0.1 to 1000 g, preferably 1 to 1000 g, more preferably 1 to 100 g, and most preferably 5 to 100 g per 100 kg of plant propagation material (preferably seeds).

[0281] Users typically apply the pesticide composition from a device with pre-set dosage, a backpack sprayer, a spray tank, a spray aircraft, or an irrigation system. Typically, the pesticide composition is prepared with water, a buffer, and / or further additives to achieve the desired application concentration, thus yielding a ready-to-use spray or pesticide composition according to the present invention. Typically, the ready-to-use spray is applied at a rate of 20 to 2000 liters, preferably 50 to 400 liters, per hectare of agriculturally usable area.

[0282] Compound I, its N-oxides, and salts can be converted into conventional types of pesticide compositions, such as solutions, emulsions, suspensions, powders, pastes, granules, presses, capsules, and mixtures thereof. Examples of composition types ("Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 6) th See also Ed. May 2008, CropLife International. These include suspensions (e.g., SC, OD, FS), emulsifying concentrates (e.g., EC), emulsions (e.g., EW, EO, ES, ME), capsules (e.g., CS, ZC), pastes, lozenges, wettable powders or powders (e.g., WP, SP, WS, DP, DS), presses (e.g., BR, TB, DT), granules (e.g., WG, SG, GR, FG, GG, MG), insecticides (e.g., LN), and gel formulations for the treatment of plant propagation materials such as seeds (e.g., GF). The compositions are prepared by known methods, such as those described, for example, by Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or by Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005. The present invention also relates to a pesticide composition comprising an auxiliary agent and at least one compound I.

[0283] Suitable auxiliary agents include solvents, liquid carriers, solid carriers or fillers, surfactants, dispersants, emulsifiers, wetting agents, adjuvants, solubilizers, penetration enhancers, protective colloids, adhesives, thickeners, humectants, repellents, attractants, feeding stimulants, compatibilizers, bactericides, antifreezes, defoamers, colorants, tackifiers, and binders.

[0284] Suitable solvents and liquid carriers include water and organic solvents, such as medium to high boiling point mineral oil fractions, e.g., kerosene, diesel oil; oils of plant or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e.g., toluene, paraffin, tetrahydronaphthalene and alkylated naphthalene; alcohols, e.g., ethanol, propanol, butanol, benzyl alcohol, cyclohexanol, glycol; DMSO; ketones, e.g., cyclohexanone; esters, e.g., lactic acid esters, carbonate esters, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g., N-methylpyrrolidone, fatty acid dimethylamide; and mixtures thereof.

[0285] Suitable solid carriers or fillers include mineral soils, such as silicates, silica gel, talc, kaolin, limestone, lime, white pigment, clay, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, such as cellulose, starch; fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea; plant-derived products, such as grain flour, bark flour, wood flour, nutmeg flour, and mixtures thereof.

[0286] Suitable surfactants include surface-active compounds, such as anionic, cationic, nonionic, and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifiers, dispersants, solubilizers, wetting agents, penetration enhancers, protective colloids, or adjuvants. Examples of surfactants are described in McCutcheon's, Vol. 1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).

[0287] Suitable anionic surfactants are alkali salts, alkaline earth salts, or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates include alkylaryl sulfonates, diphenyl sulfonates, alpha-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates, or sulfosuccinates. Examples of sulfates include sulfates of fatty acids, oils, ethoxylated alkylphenols, alcohols, ethoxylated alcohols, or fatty acid esters. Examples of phosphates include phosphate esters. Examples of carboxylates include alkyl carboxylates and carboxylated alcohols or alkylphenol ethoxylates.

[0288] Suitable nonionic surfactants include alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar-based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids, or fatty acid esters that have been alkoxylated in amounts of 1 to 50 equivalents. Ethylene oxide and / or propylene oxide, preferably ethylene oxide, can be used for alkoxylation. Examples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters, or monoglycerides. Examples of sugar-based surfactants are sorbitan, ethoxylated sorbitan, sucrose and glucose esters, or alkyl polyglucosides. Examples of polymeric surfactants are homopolymers or copolymers of vinylpyrrolidone, vinyl alcohol, or vinyl acetate.

[0289] Suitable cationic surfactants are quaternary 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 composed of blocks of polyethylene oxide and polypropylene oxide, or ABC type block polymers composed of alkanols, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are polyacrylic acid or alkali salts of polyacid comb-type polymers. Examples of polybases are polyvinylamine or polyethyleneamine.

[0290] A suitable adjuvant is a compound that has negligibly low or no pesticidal activity of its own and enhances the biological performance of compound I against the target. Examples include surfactants, mineral oils or vegetable oils, and other additives. Further examples are described in Knowles, Adjuvants and Additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.

[0291] Suitable thickeners include polysaccharides (e.g., xanthan gum, carboxymethylcellulose), inorganic clay (organically modified or unmodified), polycarboxylates, and silicates.

[0292] Suitable fungicides include bronopol and isothiazolinone derivatives, such as alkylisothiazolinone and benzisothiazolinone.

[0293] Suitable antifreezes are ethylene glycol, propylene glycol, urea, and glycerin.

[0294] Suitable defoaming agents include silicones, long-chain alcohols, and fatty acid salts.

[0295] 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, hexacyanoferrate) and organic colorants (e.g., alizarin, azo, and phthalocyanine colorants).

[0296] Suitable tackifiers or binders include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, polyacrylate, bio-derived or synthetic waxes, and cellulose ether.

[0297] The pesticide composition generally contains 0.01 to 95% by weight, preferably 0.1 to 90% by weight, more preferably 1 to 70% by weight, and especially 10 to 60% by weight of an active substance (e.g., at least one compound I). The pesticide composition generally contains 5 to 99.9% by weight, preferably 10 to 99.9% by weight, more preferably 30 to 99% by weight, and especially 40 to 90% by weight of at least one auxiliary agent. The active substance (e.g., compound I) is used with a purity of 90% to 100%, preferably 95% to 100% (as determined by NMR spectrum).

[0298] For the purpose of treating plant propagation materials, particularly seeds, seed treatment solutions (LS), saspoemulsions (SE), fluid concentrates (FS), dry treatment powders (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifying concentrates (EC), and gels (GF) are commonly used. The compositions in question exhibit an active substance concentration of 0.01 to 60% by weight, preferably 0.1 to 40%, in a ready-to-use formulation after being diluted 2 to 10 times. Application can be carried out before or during sowing. Methods for applying compound I and its compositions to plant propagation materials, particularly seeds, include powdering, coating, pelletizing, powdering, immersion, and infallo spraying. Preferably, compound I or its compositions are applied to plant propagation materials in a manner that does not induce germination, for example, by powdering, pelletizing, coating, and powdering of the seeds.

[0299] Compound I or its composition may be premixed with various types of oils, wetting agents, adjuvants, fertilizers, or micronutrients, and further pesticides (e.g., fungicides, growth regulators, herbicides, insecticides, mitigants), or may not be added until immediately before use (tank mix). These agents can be mixed with the composition according to the present invention in a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.

[0300] Pest control agents are generally chemical or biological agents (such as pest-killing components, compounds, compositions, viruses, bacteria, antimicrobial agents, or fungicides) that suppress, neutralize, kill, or otherwise eliminate harmful organisms. Target pests include insects, plant pathogens, weeds, mollusks, birds, mammals, fish, nematodes (roundworms), and microorganisms that destroy property, are nuisance, spread disease, or transmit disease. The term “pesticide” includes plant growth regulators that alter the expected rate of plant growth, flowering, or reproduction; defoliants that cause leaves or other branches to fall from plants, usually to facilitate harvesting; desiccants that promote the drying of living tissues, such as unwanted plant apex; plant activators that activate plant physiology to protect against specific pests; antidotes that reduce the undesirable herbicidal effects of pesticides in crop plants; and plant growth promoters that affect plant physiology to increase, for example, plant growth, biomass, yield, or any other quality parameter of the harvestable product of a crop plant.

[0301] Biocides are defined as forms of pesticides based on microorganisms (bacteria, fungi, viruses, nematodes, etc.) or natural products (compounds such as metabolites, proteins, or extracts from organisms or other natural sources) (U.S. Environmental Protection Agency: http: / / www.epa.gov / pesticides / biopesticides / ). Biocides are divided into two main classes: microbial pesticides and biochemical pesticides. (1) Microbial pesticides consist of bacteria, fungi, or viruses (and often include metabolites produced by bacteria and fungi). Entomopathogenic nematodes are also classified as microbial pesticides, although they are multicellular. (2) Biochemical pesticides are naturally occurring substances that control pests or provide other crop protection uses as defined below, but are relatively harmless to mammals.

[0302] When compound I, or compositions containing it, are used as fungicides, are mixed with other fungicides, it often results in an expansion of the fungicidal spectrum of activity or prevention of the development of fungicide resistance. Furthermore, synergistic effects are often obtained (synergistic mixtures).

[0303] The following list of biological agents II that can be used in combination with compound I is intended to illustrate possible combinations, but is not limited to them: A) A) Respiratory inhibitors - Complex III Q oSite-specific inhibitors: Azoxystrobin (A.1.1), Cmetoxystrobin (A.1.2), Chromoxystrobin (A.1.3), Dimoxystrobin (A.1.4), Enestrobulin (A.1.5), Phenaminestrobin (A.1.6), Phenoxystrobin / Fluphenoxystrobin (A.1.7), Fluoxastrobin (A.1.8), Kresoxime-methyl (A.1.9), Mandestrobin (A.1.10), Metminostrobin (A.1.11), Orysastrobin (A.1.12), Picoxystrobin (A.1.13), Pyraclostrobin (A.1.14), Pyramethostrobin (A.1.15), Pyraoxystrobin (A.1.16), Trifloxystrobin (A.1.17), 2-(2-(3-(2,6-dichlorophenyl)-1-methyl-arylideneaminooxymethyl)-phenyl)-2-methoxyimino-N-methylacetamide (A.1.18), Pyribencarb (A.1.19), Triclopyricarb / Chlorozincarb (A.1.20), Famoxadone (A.1.21), Phenamidone (A.1.21), Methyl-N-[2-[(1,4-dimethyl-5-phenylpyrazole-3-yl)oxymethyl]phenyl]-N-methoxycarbamate (A.1.22), Methyltetraprole (A.1.25), (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazole-3-yl]-oxy-2-methoxy Cyimino-N,3-dimethylpento-3-enamide (A.1.34), (Z,2E)-5-[1-(4-chlorophenyl)pyrazole-3-yl]oxy-2-methoxyimino-N,3-dimethylpento-3-enamide (A.1.35), pyriminostrobin (A.1.36), bifjunchi (A.1.37), 2-(ortho-((2,5-dimethylphenyl-oxymethylene)phenyl)-3-methoxy-acrylate methyl ester (A.1.38); - Complex III Q iSite-specific inhibitors: cyazofamide (A.2.1), amisulbrom (A.2.2), [(6S,7R,8R)-8-benzyl-3-[(3-hydroxy-4-methoxypyridine-2-carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxonan-7-yl]2-methylpropanoate (A.2.3), fenpicoxamide (A.2.4), florylpicoxamide (A.2.5), methallylpicoxamide (A.2.6); -Inhibitors of Complex II: benodanil (A.3.1), benzovindiflupir (A.3.2), bixafen (A.3.3), boscalid (A.3.4), carboxyne (A.3.5), fenflam (A.3.6), fluopyram (A.3.7), flutolanil (A.3.8), fluxapiroxad (A.3.9), flametopir (A.3.10), isofetamide (A.3.11), isopyrazam (A.3.12), mepronil (A.3.13), oxycarboxyne (A.3.14), penflufen (A.3.15), Penthiopyrad (A.3.16), Pidiflumetofen (A.3.17), Pyraziflumid (A.3.18), Sedaxane (A.3.19), Tecrophthalam (A.3.20), Tifluzamide (A.3.21), Impilfluxam (A.3.22), Pirapropoine (A.3.23), Fluindapir (A.3.28), N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-5-fluoro-1-methylpyrazole-4-carboxamide (A.3.29), Methyl (E )-2-[2-[(5-cyano-2-methylphenoxy)methyl]phenyl]3-methoxyprop-2-enoate (A.3.30), isoflucipram (A.3.31), 2-(difluoromethyl)-N-(1,1,3-trimethylindan-4yl)-pyridine-3-carboxamide (A.3.32), 2-(difluoromethyl)-N-[(3R)-1,1,3-trimethylindan-4-yl]pyridine-3-carboxamide (A.3.33), 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl (Difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethylindan-4-yl]pyridine-3-carboxamide (A.3.34), 2-(Difluoromethyl)-N-(1,1-dimethyl-3-propylindan-4-yl)pyridine-3-carboxamide (A.3.35), 2-(Difluoromethyl)-N-(1,1-dimethyl-3-propylindan-4-yl)pyridine-3-carboxamide (A.3.36), 2-(Difluoromethyl)-N-[(3R)-1,1-dimethyl-3-propylindan-4-yl]pyridine-3-carboxamide (A.3.37), 2-(difluoromethyl)-N-(3-isobutyl-1,1-dimethylindan-4-yl)pyridine-3-carboxamide (A.3.38), 2-(difluoromethyl)-N-[(3R)-3-isobutyl-1,1-dimethylindan-4-yl]pyridine-3-carboxamide (A.3.39), cyclobutrifluram (A.3.24); -Other respiratory inhibitors: diflumetrim (A.4.1); nitrophenyl derivatives: binapacril (A.4.2), dinovton (A.4.3), dinocap (A.4.4), fluazinam (A.4.5), meptyldinocap (A.4.6), ferimzon (A.4.7); organometallic compounds: fentin salts, e.g., fentin acetate (A.4.8), fentin chloride (A.4.9), or fentin hydroxide (A.4.10); ametoctrazine (A.4.11); silthiofam (A.4.12); B) Sterol biosynthesis inhibitors (SBI fungicides) -C14 demethylase inhibitors: Triazoles: Azaconazole (B.1.1), Vitertanol (B.1.2), Bromuconazole (B.1.3), Cyproconazole (B.1.4), Difenoconazole (B.1.5), Diniconazole (B.1.6), Diniconazole-M (B.1.7), Epoxyconazole (B.1.8), Fenbuconazole (B.1.9), Fluquinconazole (B.1.10), Flusilazole (B.1.11), Flutriahol (B.1.12), Hexaconazole (B.1.13), Imibenconazole ( B.1.14), Ipconazole (B.1.15), Metconazole (B.1.17), Mycrobutanil (B.1.18), Oxpoconazole (B.1.19), Paclobutrazol (B.1.20), Penconazole (B.1.21), Propiconazole (B.1.22), Prothioconazole (B.1.23), Simeconazole (B.1.24), Tebuconazole (B.1.25), Tetraconazole (B.1.26), Triadimefon (B.1.27), Triadimenol (B.1.28), Triticonazole (B.1.29), Uniconazole Zol (B.1.30), 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(2,2,2-trifluoroethoxy)phenyl]-2-pyridyl]propan-2-ol (B.1.31), 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazol-1-yl)-1-[5-[4-(trifluoromethoxy)phenyl]-2-pyridyl]propan-2-ol (B.1.32), fluoxythioconazole (B.1.33), ipfentrifluconazole (B.1.37), Mefentrifluconazole (B.1.38) (2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazole-1-yl)propan-2-ol, (2S)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1,2,4-triazole-1-yl)propan-2-ol, 2-(chloromethyl)-2-methyl-5-(p-tolylmethyl)-1-(1,2,4-triazole-1-ylmethyl)cyclopentanol (B.1.43); Imidazoles: Imazalil (B.1.44), Peflazoate (B.1.45), Prochloraz (B.1.46), Triflumizole (B.1.47); Pyrimidines, Pyridines, Piperazines: Phenalimol (B.1.49), Pyriphenox (B.1.50), Triforine (B.1.51), [3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)isoxazole-4-yl]-(3-pyridyl)methanol (B.1.52), 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazole-1-yl)propyl]-3-pyridyl]oxy]benzonitrile (B.1.53) , 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazole-1-yl)propan-2-ol (B.1.54), 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazole-1-yl)propan-2-ol (B.1.55), 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazole-1-yl)propanoate methyl (B.1.56), 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazole-1-yl)propanoate methyl (B.1.57);. -Delta-14-reductase inhibitors: Algimorph (B.2.1), Dodemorph (B.2.2), Acetate Dodemorph (B.2.3), Fenpropimorph (B.2.4), Tridemorph (B.2.5), Fenpropidine (B.2.6), Piperalin (B.2.7), Spiroxamine (B.2.8); -3-Ketreductase inhibitors: Fenhexamide (B.3.1); -Other sterol biosynthesis inhibitors: chlorphenomizole (B.4.1); C) Nucleic acid synthesis inhibitors - Phenylamide or acyl amino acid fungicides: Benalaxyl (C.1.1), Benalaxyl-M (C.1.2), Kiralaxyl (C.1.3), Metalaxyl (C.1.4), Metalaxyl-M (C.1.5), Offrace (C.1.6), Oxadixyl (C.1.7); -Other nucleic acid synthesis inhibitors: Himexazole (C.2.1), Octylinone (C.2.2), Oxolinic acid (C.2.3), Bupirimate (C.2.4), 5-Fluorocytosine (C.2.5), 5-Fluoro-2-(p-Tolylmethoxy)pyrimidine-4-amine (C.2.6), 5-Fluoro-2-(4-Fluorophenylmethoxy)pyrimidine-4-amine (C.2.7), 5-Fluoro-2(4-Chlorophenylmethoxy)pyrimidine-4-amine (C.2.8); D) Inhibitors of cell division and the cytoskeleton -Tubulin inhibitors: Benomyl (D.1.1), Carbendazim (D.1.2), Fuberidazole (D.1.3), Thiabendazole (D.1.4), Thiophanate-methyl (D.1.5), Pyridaclomethyl (D.1.6), N-ethyl-2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]butanamide (D.1.8), N-ethyl-2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methylsulfanylacetamide (D.1.9), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)butanamide (D.1.10), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)-2-methoxyacetamide (D.1.11), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-propyl-butanamide (D.1.12), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methoxy-N-propyl-acetamide (D.1.13), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-2-methylsulfanyl-N-propyl-acetamide (D.1.14), 2-[(3-ethynyl-8-methyl-6-quinolyl)oxy]-N-(2-fluoroethyl)-2-methylsulfanyl-acetamide (D.1.15), 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-2,5-dimethylpyrazole-3-amine (D.1.16); -Other cell division inhibitors: diethofencarb (D.2.1), etaboxam (D.2.2), pencyclon (D.2.3), fluopicolide (D.2.4), zoxamide (D.2.5), metraphenone (D.2.6), pyriophenone (D.2.7), phenamacryl (D.2.8); E) Amino acid and protein synthesis inhibitors - Methionine synthesis inhibitors: cyprodinil (E.1.1), mepanipyrim (E.1.2), pyrimethanil (E.1.3); - Protein synthesis inhibitors: Blastocydin-S (E.2.1), Kasugamycin (E.2.2), Kasugamycin hydrochloride hydrate (E.2.3), Mildiomycin (E.2.4), Streptomycin (E.2.5), Oxytetracycline (E.2.6); F) Signal transduction inhibitors -MAP / histidine kinase inhibitors: fluoroimide (F.1.1), iprodione (F.1.2), procymidone (F.1.3), vinclozoline (F.1.4), fludioxonil (F.1.5); - G protein inhibitors: quinoxifen (F.2.1); G) Lipid and membrane synthesis inhibitors - Phospholipid biosynthesis inhibitors: edifenphos (G.1.1), ipropenphos (G.1.2), pyrazophos (G.1.3), isoprothiolane (G.1.4); - Lipid peroxidation: Dichloran (G.2.1), Quintozene (G.2.2), Technazen (G.2.3), Tolcrophosmethyl (G.2.4), Biphenyl (G.2.5), Chloroneb (G.2.6), Etridiazole (G.2.7), Zinc Thiazole (G.2.8); - Phospholipid biosynthesis and cell wall deposition: Dimethomorph (G.3.1), Fullmorph (G.3.2), Mandipropamide (G.3.3), Pyrimorph (G.3.4), Benciavalicarb (G.3.5), Iprovalicarb (G.3.6), Valifenalate (G.3.7); - Compounds that affect cell membrane permeability and fatty acids: Propamocarb (G.4.1); -Oxysterol-binding protein inhibitors: Oxathiapiproline (G.5.1), Fluoxapiproline (G.5.3), 4-[1-[2-[3-(difluoromethyl)-5-methylpyrazole-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-ylpyridine-2-carboxamide (G.5.4), 4-[1-[2-[3,5-bis(difluoromethyl)pyrazole-1-yl]acetyl]-4-piperidyl]- N-tetralin-1-ylpyridine-2-carboxamide (G.5.5), 4-[1-[2-[3-(difluoromethyl)-5-(trifluoromethyl)pyrazole-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-ylpyridine-2-carboxamide (G.5.6), 4-[1-[2-[5-cyclopropyl-3-(difluoromethyl)pyrazole-1-yl]acetyl]-4-piperidyl]-N-tetralin-1 -Il-pyridine-2-carboxamide (G.5.7), 4-[1-[2-[5-methyl-3-(trifluoromethyl)pyrazole-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.8), 4-[1-[2-[5-(difluoromethyl)8), 4-[1-[2-[5-(difluoromethyl)-3-(trifluoromethyl)pyrazole-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-yl-pyridine-2-carboxamide (G.5.8), 4-[1-[2-[5-(difluoromethyl Ruboxamide (G.5.9), 4-[1-[2-[3,5-bis(trifluoromethyl)pyrazole-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-ylpyridine-2-carboxamide (G.5.10), (4-[1-[2-[5-cyclopropyl-3-(trifluoromethyl)pyrazole-1-yl]acetyl]-4-piperidyl]-N-tetralin-1-ylpyridine-2-carboxamide (G.5.11); H) Inhibitors with multi-site activity - Inorganic active substances: Bordeaux mixture (H.1.1), copper (H.1.2), copper acetate (H.1.3), copper hydroxide (H.1.4), copper oxychloride (H.1.5), basic copper sulfate (H.1.6), sulfur (H.1.7); Thio- and dithiocarbamates: Ferbam (H.2.1), Mancozeb (H.2.2), Manebu (H.2.3), Metam (H.2.4), Methylam (H.2.5), Propineb (H.2.6), Thilam (H.2.7), Zineb (H.2.8), Ziram (H.2.9); -Organochlorine compounds: anirazine (H.3.1), chlorothalonyl (H.3.2), captahol (H.3.3), captan (H.3.4), holpet (H.3.5), diclofluanide (H.3.6), dichlorophene (H.3.7), hexachlorobenzene (H.3.8), pentachlorophenol (H.3.9) and its salts, phthalide (H.3.10), tollfluanide (H.3.11); -Guanidine etc.: Guanidine (H.4.1), Dozin (H.4.2), Dozin free base (H.4.3), Guazatine (H.4.4), Guazatine acetate (H.4.5), Iminoctadine (H.4.6), Iminoctadine triacetate (H.4.7), Iminoctadine albesilate (H.4.8), Dithianone (H.4.9), 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetraone (H.4.10); I) Cell wall synthesis inhibitors - Glucan synthesis inhibitors: validamycin (I.1.1), polyoxin B (I.1.2); - Melanin synthesis inhibitors: pyroquilon (I.2.1), tricyclazole (I.2.2), carpropamide (I.2.3), dicyclomet (I.2.4), phenoxanil (I.2.5); J) Plant defense inducers -Acibenzoral-S-methyl (J.1.1), probenazole (J.1.2), isothianil (J.1.3), thiadinyl (J.1.4), prohexadione-calcium salt (J.1.5); phosphonates: fosetyl (J.1.6), fosetylaluminum (J.1.7), phosphorous acid and its salts (J.1.8), calcium phosphonate (J.1.11), potassium phosphonate (J.1.12), potassium or sodium bicarbonate (J.1.9), 4-cyclopropyl-N-(2,4-dimethoxyphenyl)thiadiazole-5-carboxamide (J.1.10); K) Mechanism of action unknown - Bronopol (K.1.1), Quinomethionate (K.1.2), Cyflufenamid (K.1.3), Cymoxanil (K.1.4), Dazomet (K.1.5), Debacarb (K.1.6), Diclocimet (K.1.7), Diclomedin (K.1.8), Diphenzocort (K.1.9), Diphenzocort-methyl sulfate (K.1.10), Diphenylamine (K.1.11), Fenitropan (K.1.12), Fenpyrazamine (K.1.13), Flumetovel (K.1.14), Flumethylsulfolimon (K.1.60), Fursul Famide (K.1.15), Fluthianil (K.1.16), Harpin (K.1.17), Metasulfocarb (K.1.18), Nitrapyrine (K.1.19), Nitrotar Isopropyl (K.1.20), Tolprocarb (K.1.21), Oxine Copper (K.1.22), Proquinazide (K.1.23), Seboctylamine (K.1.61), Tebufloquine (K.1.24), Tecrophthalam (K.1.25), Triazoxide (K.1.26), N'-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-Dimethicone N'-(4-(4-fluoro-3-trifluoromethyl-phenoxy)-2,5-dimethylphenyl)-N-ethyl-N-methylformamidine (K.1.27), N'-[4-[[3-[(4-chlorophenyl)methyl]-1,2,4-thiadiazole-5-yl]oxy]-2,5-dimethylphenyl]-N-ethyl-N-methylformamidine (K.1.29), N'-(5-bromo-6-indan-2-yloxy-2-methyl-3-pyridyl) -N-ethyl-N-methyl-formamidine (K.1.30), N'-[5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.31), N'-[5-bromo-6-(4-isopropylcyclohexoxy)-2-methyl-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.32), N'-[5-bromo-2-methyl-6-(1-phenylethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.33), N'-(2-methyl-5-trifluoromethyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methylformamidine (K.1.34), N'-(5-difluoromethyl-2-methyl-4-(3-trimethylsilanyl-propoxy)-phenyl)-N-ethyl-N-methylformamidine (K.1.35), 2-(4-chloro-phenyl)-N-[4-(3,4-dimethoxy-phenyl)-isoxazole-5-yl]-2-prop-2-inyloxyacetamide (K.1.36), 3-[5 -(4-chlorophenyl)-2,3-dimethyl-isoxazolidine-3-yl]-pyridine (pyrisoxazole) (K.1.37), 3-[5-(4-methylphenyl)-2,3-dimethyl-isoxazolidine-3-yl]-pyridine (K.1.38), 5-chloro-1-(4,6-dimethoxypyrimidine-2-yl)-2-methyl-1H-benzimidazole (K.1.39), ethyl(Z)-3-amino-2-cyano-3-phenyl-prop-2-enoate (K.1.40), picarbutrazox (K.1.41), pentyl N -[6-[[(Z)-[(1-methyltetrazole-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate (K.1.42), Buto-3-inyl N-[6-[[(Z)-[(1-methyltetrazole-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate (K.1.43), Ipuflufenoquine (K.1.44), Quinofumeline (K.1.47), Benziothiazolinone (K.1.48), Bromotalonyl (K.1.49), 2-(6-benzyl-2-pyridyl) Nazoline (K.1.50), 2-[6-(3-fluoro-4-methoxyphenyl)-5-methyl-2-pyridyl]quinazoline (K.1.51), diclobentiazox (K.1.52), N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methyl-formamidine (K.1.53), aminopyriphen (K.1.54), fluopimomide (K.1.55), N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxyethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine (K.1.56), N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethylphenyl]-N-ethyl-N-methyl-formamidine (K.1.57), fluphenoxadiazam (K.1.58), N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]benzenecarbothioamide (K.1.59), N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]cyclopropanecarboxamide (K.1.60; International Publication No. Pamphlet No. 2018 / 177894, International Publication No. 2020 / 212513), N-((4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl)methyl)propanamide (K.1.62), 3,3,3-trifluoro-N-[[3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide (K.1.63), 3,3,3-trifluoro-N-[[2-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxa Diazole-3-yl]phenyl]methyl]propanamide (K.1.64), N-[2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]benzyl]butanamide (K.1.65), N-[[2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]-3,3,3-trifluoro-propanamide (K.1.66), 1-methoxy-1-methyl-3-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3 -yl]phenyl]methyl]urea (K.1.67), 1,1-diethyl-3-[[4-[5-[trifluoromethyl]-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea (K.1.68), N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide (K.1.69), N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide (K.1.70), 1-Methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea (K.1.71), 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]pyrrolidine-2-one (K.1.72), 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]piperidine-2-one (K.1.73), 4-[[4-[5-(trifluoromethyl)-1,2, 4-Oxadiazole-3-yl]phenyl]methyl]morpholine-3-one (K.1.74), 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one (K.1.75), 2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]isoxazolidine-3-one (K.1.76), 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3 -yl]phenyl]methyl]isoxazolidine-3-one (K.1.77), 3,3-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]piperidine-2-one (K.1.78), 2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]oxazinan-3-one (K.1.79), 1-[[3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]aze Pan-2-one (K.1.80), 4,4-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]pyrrolidine-2-one (K.1.81), 5-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]pyrrolidine-2-one (K.1.82), ethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxylate (K.1.83) N-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxamide (K.1.84), N,N-dimethyl-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]benzyl]-1H-1,2,4-triazole-3-amine (K.1.85), N-methoxy-N-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxamide (K.1.84), N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxamide (K.1.85), N-methoxy-N-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxamide (K.1.84), N,N-dimethyl-1-4), N,N-dimethyl-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]pyrazole- Xamide (K.1.86), Propyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxamide (K.1.87), N-Methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]pyrazole-4-carboxamide (K.1.88), N-Allyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]propanamide (K.1.89) 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea (K.1.90), 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea (K.1.91), N-allyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]acetamide (K.1.92), N-[4-[5-(trifluoromethyl)-1,2,4 -Oxadiazole-3-yl]benzyl]cyclopropanecarboxamide (K.1.93), 1-methyl-3-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]phenyl]methyl]urea (K.1.94), N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine (K.1.95), N'-[2-chloro-4-[(4-methoxyphenyl)methyl]-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine (K.1.96), N'-[2-chloro-4-[(4-cyanophenyl)methyl]-5-methylphenyl]-N-ethyl-N-methyl-formamidine (K.1.97), N'-[2,5-dimethyl-4-(o-tolylmethyl)phenyl]-N-ethyl-N-methyl-formamidine (K.1.98), 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide (K.1.99), 3-(3-bromo-2-fluoropheno... Xy)-6-chloro-N-[2-(2-chloro-4-methyl-phenyl)-2,2-difluoro-ethyl]-5-methylpyridazine-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-methylpyridazine-4-carboxamide (K.1.101), 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-N-[2-(3,4-dimethylphenyl)-2,2- [Difluoroethyl]-5-methylpyridazine-4-carboxamide (K.1.102), 6-chloro-3-(3-chloro-2-fluorophenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-5-methylpyridazine-4-carboxamide (K.1.103), N-[2-(2-bromo-4-methylphenyl)-2,2-difluoroethyl]-6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-5-methylpyridazine-4-carboxamide (K.1.104); L) Bio-pesticides L1) Microbial pesticides having fungicidal, bactericidal, virucidal and / or plant defense activating activity: Ampelomyces quisqualis, Aspergillus flavus, Aureobasidium pullulans, Bacillus altitudinis, B. amyloliquefaciens, B. amyloliquefaciens subspecies plantarum ssp. plantarum) (also called B. velezensis), B. megaterium, B. mojavensis, B. mycoides, B. pumilus, B. simplex, B. solisalsi, B. subtilis, B. subtilis var. amyloliquefaciens, B. velezensis, Candida oleophila, C. saitoana, Clavibacter machinanensis michiganensis (bacteriophage), Coniothyrium minitans, Cryphonectria parasitica, Cryptococcus albidus, Dilophosphora alopecuri, Fusarium oxysporum, Clonostachys rosea f. catenulateP. catenulate (also known as Gliocladium catenulatum), Gliocladium roseum, Lysobacter antibioticus, L. enzymes, Metschnikowia fructicola, Microdochium dimerum, Microsphaeropsis ochracea, Muscodor albus, Paenibacillus alvei, Paenibacillus epiphyticus, P. polymyxa, Pantoea bagans vagans), Penicillium bilaiae, Phlebiopsis gigantea, Pseudomonas sp., Pseudomonas chloraphis, Pseudozyma flocculosa, Pichia anomala, Pythium oligandrum, Sphaerodes mycoparasitica, Streptomyces griseoviridis, S. lydicus, S. violaceusniger, Talaromyces flavus T. flavus), Trichoderma asperelloides, T. asperellum, T. atroviride, T. fertile, T. gamsii, T. harmatum, T.T. harzianum, T. polysporum, T. stromaticum, T. virens, T. viride, Typhula phacorrhiza, Ulocladium oudemansii, Verticillium dahlia, Zucchini yellow mosaic virus (non-toxic strain); L2) Biochemical pesticides having fungicidal, bactericidal, virucidal, and / or plant defense activating activity: Harpin protein, Reynoutria sachalinensis extract; L3) Microbial pesticides having insecticidal activity, acaricidal activity, molluscicidal activity and / or nematicidal activity: Agrobacterium radiobacter, Bacillus cereus, B. firmus, B. thuringiensis, B. thuringiensis ssp. aizawai, Bt subspecies israelensis, Bt subspecies galleriae, Bt subspecies kurstaki, Bt subspecies tenebrionis, Beauveria bassiana Bassiana), B. brongniartii, Burkholderia spp., Chromobacterium subtsugae, Cydia pomonella granulovirus (CpGV), Cryptophlebia leucotreta granulovirus (CrleGV), Flavobacterium spp., Helicoverpa armigera nucleopolyhedrovirus (HearNPV), Helicoverpa zea nucleopolyhedrovirus Helicoverpa zea single capsid nucleopolyhedrovirus (HzNPV), Helicoverpa zea single capsid nucleopolyhedrovirus (HzSNPV), Heterorhabditis bacteriophora, Isaria fumosorosea, Lecanicillium longisporum, L. musculus (L.muscarium), Metarhizium anisopliae, M. anisopliae var. anisopliae, M. anisopliae var. acridum, Nomuraea rileyi, Paecilomyces fumosoroseus, P. lilacinus, Paenibacillus popilliae, Pasteuria (spp.), P. nishizawae, P. penetrans, P. ramosa, P. thornea, P. usgae, Pseudomonas fluorescens, Spodoptera littoralis nucleopolyhedrovirus (SpliNPV), Steinernema carpocapsae, S. feltiae, S. kraussei, Streptomyces galbus, S. microflavus; L4) Biochemical pesticides having insecticidal activity, acaricidal activity, molluscicidal activity, pheromone activity and / or nematicidal activity: L-carbone, citral, (E,Z)-7,9-dodecadiene-1-ylacetate, ethylformate, (E,Z)-2,4-ethyldecadienone (pear ester), (Z,Z,E)-7,11,13-hexadecatrienal, heptylbutyrate, isopropyl myristate, lavanuryl senesioate, cis-jasmon, 2-methyl-1-butanol, methyl eugenol, methyl jasmonate, (E,Z)-2,13-oc Tadecadien-1-ol, (E,Z)-2,13-octadecadien-1-ol acetate, (E,Z)-3,13-octadecadien-1-ol, (R)-1-octen-3-ol, pentatermanone, (E,Z,Z)-3,8,11-tetradecatrieninyl acetate, (Z,E)-9,12-tetradecadien-1-yl acetate, (Z)-7-tetradecen-2-one, (Z)-9-tetradecen-1-yl acetate, (Z)-11-tetradecenal, (Z)-11-tetradecen-1-ol, extract of American antlion (Chenopodium ambrosiodes); neem oil, quillaja extract; L5) Microbial pesticides having plant stress reduction activity, plant growth regulator activity, plant growth promoting activity and / or yield increasing activity: Azospirillum amazonense, A. brasilense, A. lipoferum, A. irakense, A. halopraeferens, Bradyrhizobium spp., B. elkanii, B. japonicum, B. liaoningense, B. lupini, Delftia acidovorans, Glomus intraradices intraradices), Mesorhizobium spp., Rhizobium leguminosarum bv. phaseoli, Rlbv. trifolii, Rlbv. viciae, R. tropici, Sinorhizobium meliloti; O) Insecticides according to class classification O.1~O.29 O.1 Acetylcholinesterase (AChE) inhibitors: Aldicarb, Alanicarb, Bendiocarb, Benfuracarb, Butocarboxime, Butoxycarboxime, Carbaryl, Carbofuran, Carbosulfan, Ethiofencarb, Phenobucarb, Formetanate, Furathiocarb, Isoprocarb, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pyrimicarb, Propoxul, Thiodicarb, Thiofanox, Trimetacarb, XMC, Xylylcarb, Triazamate, Acephate, Azamethiphos, Adinphos-ethyl, Adinphos-methyl, Kazusaphos, Chlorethoxyphos, Chlorfenbinphos, Chlormephos, Chlorpyrifos, Chlorpyrifos-methyl, Coumaphos, Cyanophos, Demeton-S-methyl, Diazinon, Dichlorvos / DDVP, Diclotophos, Dimethoate, Dimethi Rubinphos, disulfon, EPN, Ethion, Etoprophos, Famfur, Phenamiphos, Fenitrothion, Fenthion, Fostiazate, Heptenophos, Imisiaphos, Isofenphos, O-(methoxyaminothio-phosphoryl)isopropyl salicylate, Isoxathion, Malathion, Mecarbam, Metamidophos, Methidathion, Mevinphos, Monoclotophos, Nared, Omethoate, Oxidemeton-methyl, Parathion, Parathion-methyl, Fenthoate, Phosalone, Phosmet, Phosphamidone, Foxim, Pyrimiphos-methyl, Profenophos, Propetamphos, Prothiophos, Pyraclophos, Pyridafenthion, Quinalphos, Sulfotep, Tebupyrimphos, Temephos, Terbuphos, Tetrachlorvinphos, Thiometon, Triazophos, Trichlorfon, Bamidothion; O.2 GABAergic chloride channel antagonists: endosulfan, chlordane, ethiprole, fipronil, flufiprole, pyrafluprole, pyriprole; O.3 Sodium channel modulators: Acrinatrin, Arethrin, d-cis-transarethrin, d-transarethrin, Bifenthrin, Kappa-bifenthrin, Bioarethrin, Bioarethrin S-cyclopentenyl, Biorethmetrin, Cycloprotrin, Cyfluthrin, Beta-cyfluthrin, Cyhalothrin, Lambda-cyhalothrin, Gamma-cyhalothrin, Cypermethrin, Alpha-cypermethrin, Beta-cypermethrin, Theta-cypermethrin, Zeta-cypermethrin, Cyphenothrin, Deltamethrin, Empenthrin, Esfen Valerate, etofenprox, fenpropathrin, fenvalerate, flucitrinate, flumethrin, taufluvalinate, halfenprox, heptafluthrin, imiprothrin, meperfluthrin, metofluthrin, monfluorothrin, epsilonmonfluorothrin, permethrin, phenothrin, prallethrin, profluthrin, pyrethrin (chrysanthemum), resmethrin, silafluofen, tefluthrin, kappa-tefluthrin, tetramethylfluthrin, tetramethrin, tralomethrin, transfluthrin, DDT, methoxychloride; O.4 Nicotinic acetylcholine receptor (nAChR) agonists: acetamiprid, clothianidin, cycloxapride, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam; 4,5-dihydro-N-nitro-1-(2-oxyranylmethyl)-1H-imidazole-2-amine, (2E)-1-[(6-chloropyridine-3-yl)methyl]-N'-nitro-2-pentylidenehydrazine carboxyimidoamide; 1-[(6-chloropyridine-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridine; nicotine; sulfoxaflor, flupyradiflon, triflumezopyrim, fenmezoditiaz, flupyrim; O.5 Nicotinic acetylcholine receptor allosteric activators: spinosad, spinetram; O.6 Chloride channel activators: abamectin, emamectin benzoate, ivermectin, lepimectin, milbemectin; O.7 Juvenile hormone analogues: hydroprene, quinoprene, methoprene; phenoxycarb, pyriproxyfen; O.8 Various nonspecific (multisite) inhibitors: methyl bromide and other alkyl halides; chloropicrin, sulfuryl fluoride, borax, tartaric acid; O.9 String organ TRPV channel modulators: Afidopiropene, Pymetrozine, Pyrifluquinazone; O.10 Mite growth inhibitors: clofentezine, hexythiazox, diflovidazine; etoxazole; O.11 Microbial disruptors in the insect midgut membrane: Bacillus thuringiensis, B. sphaericus and the insecticidal proteins they produce: Bacillus thuringiensis subsp. Israelensis, B. sphaericus, B. thuringiensis subsp. aizawai, B. thuringiensis subsp. Kurstaki, B. thuringiensis subsp. tenebryonis Proteins found in Bt crops (subsp. Tenebrionis): Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34 / 35Ab1; O.12 Mitochondrial ATP synthase inhibitors: diafenthiurone; azocyclotin, cyhexatine, fenbutasin oxide, propargit, tetradiphon; O.13 Oxidative phosphorylation uncoupling agents that disrupt the proton gradient: chlorfenapyr, DNOC, sulfuramide; O.14 Nicotinic acetylcholine receptor (nAChR) channel blockers: bensultap, cartap hydrochloride, thiocyclam, thiosultap sodium salt; O.15 Chitin biosynthesis inhibitors type 0: Bistriflurone, Chlorfluazurone, Diflubenzuron, Flucycloxurone, Flufenoxurone, Hexaflumurone, Lufenuron, Novalon, Noviflumurone, Teflubenzuron, Triflumurone; O.16 Chitin biosynthesis inhibitor type 1: Buprofezin; O.17 Molting inhibitor: Cyromazine; O.18 Ecdysone receptor agonists: Methoxyfenozide, Tebufenozide, Halofenozide, Fufenozide, Chromafenozide; O.19 Octopamine receptor agonist: Amitraz; O.20 Mitochondrial electron transport chain complex III inhibitors: hydramethylnon, acequinosyl, fluacrylipylim, bifenazate; O.21 Mitochondrial Electron Transport Chain Complex I Inhibitors: Phenazaquine, Fenpyroximate, Pyrimidifene, Pyridaben, Tebufenpyrad, Tolfenpyrad, Rotenone; O.22 Voltage-gated sodium channel blockers: indoxacarb, metaflumizone, 2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]-hydrazinecarboxamide, N-(3-chloro-2-methylphenyl)-2-[(4-chlorophenyl)-[4-[methyl(methylsulfonyl)amino]phenyl]methylene]hydrazine Zincarboxamide, N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide, 2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]-hydrazinecarboxamide; O.23 Acetyl-CoA carboxylase inhibitors: spirodiclofen, spiromesifen, spirotetramato, spiropidione, spirobudifen, 11-(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1,4-dioxa-9-azadhispiro[4.2.4.2]tetradeca-11-en-10-one, spidoxamato; O.24 Mitochondrial Electron Transport Chain Complex IV Inhibitors: Aluminum phosphide, calcium phosphide, phosphine, zinc phosphide, cyanide: O.25 Mitochondrial electron transport chain complex II inhibitors: cyenopyrafen, cyflumetofen, cyetopyrafen, piflubum; O.28 ryanodine receptor modulators: chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubendiamide, fluchlodiniliprole, (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-chloropyridine-2-yl)-1H-pyrazole-5-yl]carbonyl}amino)benzoyl]-1,2-dimethylhydrazine carboxylate; N-[4,6-dichloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]phenyl]-2-(3-chloro (2-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[4-chloro-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6-methylphenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[2-(5-amino-1,3,4-thiadiazole-2-yl)-4-chloro-6-methylphenyl] -3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide; 3-chloro-1-(3-chloro-2-pyridinyl)-N-[2,4-dichloro-6-[[(1-cyano-1-methylethyl)amino]carbonyl]phenyl]-1H-pyrazole-5-carboxamide; tetrachlorantraniliprole; tetrachlorantraniliprole; thiolantraniliprole; N-[4-chloro-2-[ [(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide; cyhalodiamide; N-[2-(5-amino-1,3,4-thiadiazole-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide; O.29 String organ modulator: flonicamide; O.30 GABAergic chloride ion channel allosteric modulators: broflanilide, fluxamethamide, isocycloceram; O.33 Calcium-activated potassium channel modulator: Acinonapir; O.34 Inhibitor at the Qi site of mitochondrial electron transport chain complex III: Frometkin; O.UN Insecticidal compounds with unknown or unclear mechanisms of action: Afoxoleiner, azadirachtin, amidoflumet, benzoximate, bromopropylate, thinomethionate, cryolite, cyprofuranilide, dichloromezothiaz, dicofol, dinpropyridaz, fluphenerim, flomethoquin, fluensulfone, fluhexafone, fluopyram, fluralaner, metaldehyde, methoxadiazone, piperonyl butoxide, pyridaryl, thioxazafen, trifluenflonate, umiphoxolaner, 11-(4-chloro-2,6- Dimethylphenyl)-12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]-tetradeca-11-en-10-one, 3-(4'-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azadispiro[4.5]deca-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-methylbenzamide , 4-cyano-3-[(4-cyano-2-methylbenzoyl)amino]-N-[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]-2-fluorobenzamide, 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-methylbenzamide, N-[5-[[[2-bromo-6-chloro-4 -[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]amino]carbonyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide, N-[5-[[[2-bromo-6-chloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]amino]carbonyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide, 4-cyano-N-[2-cyano-5-[[[2,6-dichloro-4-[1,2,2,3,3,3-Hexafluoro-1-(trifluoromethyl)propyl]phenyl]amino]carbonyl]phenyl]-2-methyl-benzamide, 1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1H-1,2,4-triazole-5-amine, N-[5-[[[2-bromo-6-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]amino]carbonyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide, 4-cyano-N-[2-cyano-5-[[[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]amino]carbonyl]phenyl]-2-methyl-benzamide, Bacillus films firmus (Votivo, I-1582) based surfactants; fluazandinidine; 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-cyanophenyl]-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]carbamoyl]phenyl]-2-methyl-benzamide;4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide;N-[5-[[2-bromo-6-chloro-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide;2-(1,3-Dioxan-2-yl)-6-[2-(3-pyridinyl)-5-thiazolyl]-pyridine; 2-[6-[2-(5-fluoro-3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine; 2-[6-[2-(3-pyridinyl)-5-thiazolyl]-2-pyridinyl]-pyrimidine; N-methylsulfonyl-6-[2-(3-pyridyl)thiazolyl-5-yl]pyridine-2-carboxamide; N-methylsulfonyl-6-[2-(3-pyridyl)thiazolyl-5-yl]pyridine-2-carboxamide; 1-[(6-chloro-3-pyridinyl) [(6-chloropyridinyl)methyl]-1,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitroimidazo[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]-hydrazinecarboxamide; 1-[(6-chloro-3-pyridinyl)methyl]-1,2,3,5, 6,7-Hexahydro-5-methoxy-7-methyl-8-nitroimidazo[1,2-a]pyridine; 2-(3-pyridinyl)-N-(2-pyrimidinylmethyl)-2H-indazole-5-carboxamide; ticlopyrazoflor; saloraner, rotilaner; 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-(3-ethylsulfonyl-2-pyridyl)-3-methyl-6-(tri-fluoromethyl)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; benzpyrimoxane; tigoraner; oxazosulfyl; [(2S,3R,4R,5S,6S)-3,5-dimethoxy-6-methyl-4-propoxy-tetrahydropyran-2-yl]-N-[4-[1-[4-(trifluoromethoxy) [phenyl]-1,2,4-triazole-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-triazole-3-yl]phenyl]carbamate; [(2S,3R,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 -triazole-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-triazole-3-yl]phenyl]carbamate; (2Z)-3-(2-isopropylphenyl)-2-[(E)-[4-[1-[4-(trifluoromethoxy)phenyl]-1,2,4-triazole-3-yl]phenyl]methylenehydrazono]thiazolidined-4-one, ( 2Z)-3-(2-isopropylphenyl)-2-[(E)-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazole-3-yl]phenyl]methylenehydrazono]thiazolidined-4-one, (2Z)-3-(2-isopropylphenyl)-2-[(E)-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazole-3-yl]phenyl]methylenehydrazono]thiazolidined-4-one; 2-(6-chloro-3-ethylsulfonyl-imidazo[1,2-a]pyridine-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-(6-bromo-3-ethylsulfonyl-imidazo[1,2-a]pyridine-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-(3-ethylsulfonyl-6-iodoimidazo[1,2-a]pyridine-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-(7-chloro-3-ethylsulfonyl-imidazo[1,2-a]pyridine-2-yl )-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-(7-chloro-3-ethylsulfonyl-imidazo[1,2-a]pyridine-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-(3-ethylsulfonyl-7-iodo-imidazo[1,2-a]pyridine-2-yl)-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 3-ethylsulfonyl-6-iodo-2-[3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine -2-yl]imidazo[1,2-a]pyridine-8-carbonitride, 2-[3-ethylsulfonyl-8-fluoro-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-yl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-[3-ethylsulfonyl-7-(trifluoromethyl)imidazo[1,2-a]pyridine-2-yl]-3-methyl-6-(trifluoromethylsulfinyl)imidazo[4,5-b]pyridine, 2-[3-ethylsulfonyl-7-(trifluoromethyl)imidazo [1,2-a]pyridine-2-yl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-c]pyridine, 2-(6-bromo-3-ethylsulfonyl-imidazo[1,2-a]pyridine-2-yl)-6-(trifluoromethyl)pyrazolo[4,3-c]pyridine; N-[[2-fluoro-4-[(2S,3S)-2-hydroxy-3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrroridine-1-yl]phenyl]methyl]cyclopropanecarboxamide; 2-[2-fluoro-4-methyl-5-(2,2,2-Trifluoroethylsulfinyl)phenyl]imino-3-(2,2,2-trifluoroethyl)thiazolidin-4-one; Flupenthiophenox, N-[3-chloro-1-(3-pyridyl)pyrazole-4-yl]-2-methylsulfonylpropanamide, cyclobutrifluram; N-[4-chloro-3-[(1-cyanocyclopropyl)carbamoyl]phenyl]-2-methyl-4-methylsulfonyl-5-(1,1,2,2,2-pentafluoroethyl)pyrazole-3-carboxamide, cyproflanilide, nicoflurprole; 1,4-dimethyl-2-[2-(pyridin-3-yl)-2H-indazole-5-yl]-1,2,4-triazolidine-3,5-dione, 2-[2-fluoro-4-methyl-5-, (2,2,2-trifluoroethylsulfanyl)phenyl]imino-3-(2,2,2-trifluoroethyl)thiazolidinion-4-one, indazapyroxameth, N-[4-chloro-2-(3-pyridyl)thiazole-5-yl]-N-ethyl-3-methylsulfonylpropanamide, N-cyclopropyl-5-[(5S)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4H-isoxazole-3-yl]isoquinoline-8-carboxamide, 5-[(5S)-5-(3,5-dichloro-4-fluorophenyl)-5-(trifluoromethyl)-4H-isoxazole-3-yl]-N-(pyrimidine-2-ylmethyl)isoquinoline-8-carboxamide, N-[1 -(2,6-difluorophenyl)pyrazole-3-yl]-2-(trifluoromethyl)benzamide, 5-((1R,3R)-3-(3,5-bis(trifluoromethyl)phenyl)-2,2-dichlorocyclopropane-1-carboxamide)-2-chloro-N-(3-(2,2-difluoroacetamide)-2,4-difluorophenyl)benzamide, 1-[6-(2,2-difluoro-7-methyl-[1,3]dioxolo[4,5-f]benzimidazole-6-yl)-5-ethylsulfonyl-3-pyridyl]cyclopropanecarbonitride, 6-(5-cyclopropyl-3-ethylsulfonyl-2-pyridyl)-2,2-difluoro-7-methyl-[1,3]dioxolo[4,5-f]benzimidazole.

[0304] The active substance referred to as component 2, its preparation, and its activity, for example, its activity against harmful fungi, are publicly known (see http: / / www.alanwood.net / pesticides / ), and these substances are commercially available. The compounds described in IUPAC nomenclature, their preparation, and their pesticidal activity are also publicly known (Can.J.Plant Sci.48(6),587-94,1968; European Patent Application Publication A141317; European Patent Application Publication A152031; European Patent Application Publication A226917; European Patent Application Publication A243970; European Patent Application Publication A256503; European Patent Application Publication A428941; European Patent Application Publication A532022; European Patent Application Publication A1028125; European Patent Application Publication A1035122 Specification No.; European Patent Application Publication No. A1201648; European Patent Application Publication No. A1122244; Japanese Patent Publication No. 2002316902; German Patent No. 19650197; German Patent No. 10021412; German Patent No. 102005009458; US Patent No. 3,296,272; US Patent No. 3,325,503; International Publication No. 98 / 46608; International Publication No. 99 / 14187; International Publication No. Pamphlet No. 99 / 24413; International Publication No. 99 / 27783; International Publication No. 00 / 29404; International Publication No. 00 / 46148; International Publication No. 00 / 65913; International Publication No. 01 / 54501; International Publication No. 01 / 56358; International Publication No. 02 / 22583; International Publication No. 02 / 40431; International Publication No. 03 / 10149; International Publication Pamphlet No. 03 / 11853; Pamphlet No. 03 / 14103 (International Publication); Pamphlet No. 03 / 16286 (International Publication); Pamphlet No. 03 / 53145 (International Publication); Pamphlet No. 03 / 61388 (International Publication); Pamphlet No. 03 / 66609 (International Publication); Pamphlet No. 03 / 74491 (International Publication); Pamphlet No. 04 / 49804 (International Publication); Pamphlet No. 04 / 83193 (International Publication); Pamphlet No. 05 / 120234 (International Publication);International Publication Brochure No. 05 / 123689; International Publication Brochure No. 05 / 123690; International Publication Brochure No. 05 / 63721; International Publication Brochure No. 05 / 87772; International Publication Brochure No. 05 / 87773; International Publication Brochure No. 06 / 15866; International Publication Brochure No. 06 / 87325; International Publication Brochure No. 06 / 87343; International Publication Brochure No. 07 / 82098; International Publication Brochure No. 07 / 90624; International Publication Brochure No. 10 / 139271; International Publication Brochure No. 11 / 0286 Pamphlet No. 57; International Publication No. 12 / 168188; International Publication No. 07 / 006670; International Publication No. 11 / 77514; International Publication No. 13 / 047749; International Publication No. 10 / 069882; International Publication No. 13 / 047441; International Publication No. 03 / 16303; International Publication No. 09 / 90181; International Publication No. 13 / 007767; International Publication No. 13 / 010862; International Publication No. 13 / 127704 T; International Publication No. 13 / 024009 brochure; International Publication No. 13 / 24010 brochure; International Publication No. 13 / 047441 brochure; International Publication No. 13 / 162072 brochure; International Publication No. 13 / 092224 brochure; International Publication No. 11 / 135833 brochure; Chinese Patent Application Publication No. 1907024 specification; Chinese Patent Application Publication No. 1456054 specification; Chinese Patent Application Publication No. 103387541 specification; Chinese Patent Application Publication No. 1309897 specification; International Publication No. 12 / 84812 brochure; Chinese Patent Application Publication No. 1907024; International Publication No. 09094442; International Publication No. 14 / 60177; International Publication No. 13 / 116251; International Publication No. 08 / 013622; International Publication No. 15 / 65922; International Publication No. 94 / 01546; European Patent No. 2865265; International Publication No. 07 / 129454; International Publication No. 12 / 165511; International Publication No. 11 / 081174; International Publication No. 13 / 47441;See International Publication No. 16 / 156241 and International Publication No. 16 / 162265. Some compounds are identified by their CAS Registry Number, which is divided into three parts by a hyphen: the first part consists of 2 to 7 digits, the second part consists of 2 digits, and the third part consists of 1 digit.

[0305] According to the present invention, the solid substance (dried substance) of a bio-pesticide (excluding oils such as neem oil) is considered the active ingredient (for example, in the case of a liquid formulation of a microbial pesticide, it is obtained after drying or evaporation of the extraction or suspension medium). The weight ratios and percentages used for biological extracts such as quillaja extract are based on the total weight of the dry content (solid substance) of each extract.

[0306] The total weight ratio of a composition containing at least one microbial pesticide in the form of a viable microbial cell, including a dormant form, is 1 × 10⁻⁶ 10 The total weight of each active ingredient can be calculated using the amount of CFU of each microorganism, based on the equation that CFU equals 1 gram of the total weight of each active ingredient. Colony-forming units are a measure of viable microbial cells. Furthermore, in the case of nematode biocides such as Steinernema feltiae, CFU can be understood as the number of individual (immature) nematodes.

[0307] In a binary mixture, the weight ratio of component 1) to component 2) generally depends on the properties of the components used, and is typically in the range of 1:10,000 to 10,000:1, often 1:100 to 100:1, usually 1:50 to 50:1, preferably 1:20 to 20:1, more preferably 1:10 to 10:1, even more preferably 1:4 to 4:1, and particularly 1:2 to 2:1. According to further embodiments, the weight ratio of component 1) to component 2) is typically in the range of 1000:1 to 1:1, often 100:1 to 1:1, usually 50:1 to 1:1, preferably 20:1 to 1:1, more preferably 10:1 to 1:1, even more preferably 4:1 to 1:1, and particularly 2:1 to 1:1. In further embodiments, the weight ratio of component 1) to component 2) is typically in the range of 20,000:1 to 1:10, often 10,000:1 to 1:1, usually 5,000:1 to 5:1, preferably 5,000:1 to 10:1, more preferably 2,000:1 to 30:1, even more preferably 2,000:1 to 100:1, and particularly 1,000:1 to 100:1. In further embodiments, the weight ratio of component 1) to component 2) is typically in the range of 1:1 to 1:1000, often 1:1 to 1:100, usually 1:1 to 1:50, preferably 1:1 to 1:20, more preferably 1:1 to 1:10, even more preferably 1:1 to 1:4, and particularly 1:1 to 1:2. In further embodiments, the weight ratio of component 1) to component 2) is typically in the range of 10:1 to 1:20,000, often 1:1 to 1:10,000, usually 1:5 to 1:5,000, preferably 1:10 to 1:5,000, more preferably 1:30 to 1:2,000, even more preferably 1:100 to 1:2,000, and particularly 1:100 to 1:1,000.

[0308] 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 properties of the active substance used and is typically in the range of 1:100 to 100:1, usually 1:50 to 50:1, preferably 1:20 to 20:1, more preferably 1:10 to 10:1, and particularly 1:4 to 4:1. The weight ratio of component 1) to component 3) is typically in the range of 1:100 to 100:1, usually 1:50 to 50:1, preferably 1:20 to 20:1, more preferably 1:10 to 10:1, and particularly 1:4 to 4:1. Any further active ingredients may be added as needed in a ratio of 20:1 to 1:20 relative to component 1). These ratios are also suitable for mixtures applied by seed treatment.

[0309] When a mixture containing microbial pesticides is used for crop protection, the application rate is 1 × 10⁻⁶. 6 ~5×10 16 (or more) CFU / ha, preferably 1 × 10⁻⁶ 8 ~1 × 10 13 CFU / ha, even more preferably 1 × 10 9 ~5×10 15 CFU / ha, especially 1 × 10⁻⁶ 12 ~5×10 14 The range is CFU / ha. In the case of nematodes (e.g., Steinernema feltiae) as microbial pesticides, the application rate is usually 1 × 10⁻¹⁶ per hectare. 5 ~1 × 10 12 (or more), preferably 1 × 10 8 ~1 × 10 11 , comfortable 5×10 8 ~1 × 10 10 This ranges from individual organisms (for example, eggs, juveniles, or any other stage of life, preferably in the immature juvenile stage).

[0310] When using a mixture containing microbial pesticides for seed treatment, the application rate is generally 1 × 10⁻⁶. 6 ~1 × 10 12 (or more) CFU / seed, preferably 1 × 10 6~1 × 10 9 The range is CFU / seed. Furthermore, the application rate for seed treatment is generally 1 × 10⁶ per 100 kg of seed. 7 ~1 × 10 14 (or more) CFU, preferably 1 × 10 per 100 kg of seeds 9 ~1 × 10 12 This falls under the scope of CFU.

[0311] Component 2) is Q from group A). o A mixture containing at least one active substance selected from inhibitors of complex III at the site, more preferably 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); in particular, a mixture containing at least one active substance selected from (A.1.1), (A.1.4), (A.1.8), (A.1.9), (A.1.13), (A.1.14), (A.1.17), (A.1.25), (A.1.34), and (A.1.35) is preferred.

[0312] Component 2) is Q from group A). i A mixture containing at least one active substance selected from (A.2.3), (A.2.4), and (A.2.6) is preferred, which is selected from inhibitors of complex III at the site; more preferably from compounds (A.2.1), (A.2.3), (A.2.4), and (A.2.6).

[0313] As component 2), a compound selected from the inhibitors of complex II of group A), more preferably (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 mixture containing at least one active substance selected from (A.3.37), (A.3.38), and (A.3.39) is preferred; in particular, a mixture containing at least one active substance selected from (A.3.2), (A.3.3), (A.3.4), (A.3.7), (A.3.9), (A.3.12), (A.3.15), (A.3.17), (A.3.19), (A.3.22), (A.3.23), (A.3.24), (A.3.31), (A.3.32), (A.3.33), (A.3.34), (A.3.35), (A.3.36), (A.3.37), (A.3.38), and (A.3.39) is preferred.

[0314] Component 2) is at least one active substance selected from other respiratory inhibitors of group A), more preferably selected from compounds (A.4.5) and (A.4.11); a mixture containing (A.4.11) is also preferred.

[0315] As component 2), more preferably a compound selected from the C14 demethylase inhibitors of group B) (B.1.4), (B.1.5), (B.1.8), (B.1.10), (B.1.11), (B.1.12), (B.1.13), (B.1.17), (B.1.18), (B.1.21), (B.1.22), (B.1.23), (B.1.25), (B.1.26), (B.1.29), (B.1.34), (B.1.37), (B.1.38), A mixture containing at least one active substance selected from (B.1.43), (B.1.46), (B.1.53), (B.1.54), and (B.1.55) is also preferred; in particular, a mixture containing at least one active substance selected from (B.1.5), (B.1.8), (B.1.10), (B.1.17), (B.1.22), (B.1.23), (B.1.25), (B.1.33), (B.1.34), (B.1.37), (B.1.38), (B.1.43), and (B.1.46) is also preferred.

[0316] As component 2), a mixture containing at least one active substance selected from delta-14-reductase inhibitors of group B, more preferably compounds (B.2.4), (B.2.5), (B.2.6), and (B.2.8); particularly preferably (B.2.4), is also preferred.

[0317] As component 2), a mixture containing at least one active substance selected from phenylamide and acyl amino acid fungicides of group C) is also preferred; more preferably, a mixture containing at least one active substance selected from (C.1.1) and (C.1.4) is also preferred.

[0318] A mixture containing, as component 2), at least one active substance selected from other nucleic acid synthesis inhibitors of group C), more preferably from compounds (C.2.6), (C.2.7), and (C.2.8), is also preferred.

[0319] As component 2), a mixture containing at least one active substance selected from group D) is also preferred, more preferably from compounds (D.1.1), (D.1.2), (D.1.5), (D.2.4), and (D.2.6); in particular from (D.1.2), (D.1.5), and (D.2.6).

[0320] Component 2) is at least one active substance selected from group E), more preferably from compounds (E.1.1), (E.1.3), (E.2.2), and (E.2.3); a mixture containing (E.1.3) is also preferred.

[0321] As component 2), a mixture containing at least one active substance selected from group F), more preferably from compounds (F.1.2), (F.1.4), and (F.1.5), is also preferred.

[0322] As component 2), a compound selected from group G), more preferably from compounds (G.3.1), (G.3.3), (G.3.6), (G.5.1), (G.5.3), (G.5.4), (G.5.5), (G.5.6), (G.5.7), (G.5.8), (G.5.9), (G.5.10), and (G.5.11); a mixture containing at least one active substance selected from (G.3.1), (G.5.1), and (G.5.3) is also preferred.

[0323] As component 2), a mixture containing at least one active substance selected from group H) is also preferred, 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); in particular, from (H.2.2), (H.2.5), (H.3.2), (H.4.9), and (H.4.10).

[0324] A mixture containing at least one active substance selected from group I, more preferably from compounds (I.2.2) and (I.2.5), is also preferred as component 2).

[0325] Component 2) is at least one active substance selected from group J), more preferably from compounds (J.1.2), (J.1.5), (J.1.8), (J.1.11), and (J.1.12); a mixture containing (J.1.5) is also preferred.

[0326] As component 2), a mixture containing at least one active substance selected from group K) is also preferred, more preferably from compounds (K.1.41), (K.1.42), (K.1.44), (K.1.47), (K.1.57), (K.1.58), and (K.1.59); in particular from (K.1.41), (K.1.44), (K.1.47), (K.1.57), (K.1.58), and (K.1.59).

[0327] Biocides from group L1) and / or group L2) may also possess insecticidal activity, acaricidal activity, molluscicidal activity, pheromone activity, nematicidal activity, plant stress reduction activity, plant growth regulator activity, plant growth promotion activity, and / or yield-increasing activity. Biocides from group L3) and / or group L4) may also possess fungicidal activity, bactericidal activity, virucidal activity, plant defense activator activity, plant stress reduction activity, plant growth regulator activity, plant growth promotion activity, and / or yield-increasing activity. Biocides from group L5) may also possess fungicidal activity, bactericidal activity, virucidal activity, plant defense activator activity, insecticidal activity, acaricidal activity, molluscicidal activity, pheromone activity, and / or nematicidal activity.

[0328] Microbial pesticides, particularly those from groups L1), L3), and L5), include not only isolated pure cultures of each microorganism as defined herein, but also cell-free extracts thereof, their suspensions in whole broth cultures, and metabolite-containing culture media or purified metabolites obtained from whole broth cultures of microorganisms.

[0329] Many of these biocides are deposited under the deposit numbers mentioned herein (prefixes such as ATCC or DSM refer to acronyms for each culture collection; see, for example, http: / / www.wfcc.info / ccinfo / collection / by_acronym / ), mentioned in the literature, registered, and / or commercially available: a mixture of Aureobasidium pullulans DSM 14940 and DSM 14941 isolated in Konstanz, Germany in 1989 (e.g., spores in BlossomProtect® from bio-ferm GmbH, Austria); and Azospirillum brasilense Sp245 (BR11005), originally isolated in the wheat region of South Brazil (Passo Fundo) at least before 1980; e.g., BASF Agricultural Specialties. GELFIX® (Grameneas) from Ltd., Brazil; A. brasilense strains Ab-V5 and Ab-V6 (e.g., in AzoMax from Novozymes BioAg Produtos papra Agricultura Ltda., Quattro Barras, Brazil or Simbiose-Agro from Simbiose-Maiz® from Brazil; Plant Soil 331, 413-425, 2010); Bacillus amyloliquefaciens strain AP-188 (NRRL B-50615 and B-50331; U.S. Patent No. 8,445,255); B. amyloliquefaciens subspecies plantarum (B. amyloliquefaciens (ssp. plantarum) strain (formerly sometimes called B. subtilis, and now classified as B. velezensis along with B. methylotrophicus and B. velezensis) (Int. J. Syst. Evol.Microbiol. 66, 1212-1217, 2016): Bassp. plantarum or B. velezensis D747 isolated from the air in Kikugawa City, Japan (US Patent Application No. 20130236522A1; FERM BP-8234; e.g., Double Nickel (trademark) 55 WDG from Certis LLC, USA), and Bassp. plantarum or B. velezensis FZB24 (also known as SB3615; DSM96-2; J. Plant Dis. Prot. 105, 181-197, 1998; e.g., Novozyme Bassp. plantarum or B. velezensis FZB42 (DSM23117; J. Plant Dis. Prot. 105, 181-197, 1998; e.g., RhizoVital® 42 from AbiTEP GmbH, Germany), Bassp. plantarum or B. velezensis MBI600 (also known as 1430; NRRL B-50595; U.S. Patent Application Publication No. 2012 / 0149571A1); e.g., BASF Integral (registered trademark) from Bayer Crop Science LP, USA; Bassp. plantarum or B. velezensis QST-713 (NRRL B-21661; e.g., Serenade (registered trademark) MAX from Bayer Crop Science LP, USA); Bassp. plantarum isolated in 1992 in South Dakoda, USA.B. plantarum) or B. velezensis TJ1000 (also known as 1BE; ATCC BAA-390; Canadian Patent Application Publication No. 2471555A1; e.g., QuickRoots® from TJ Technologies, Watertown, SD, USA), B. firmus CNCM I-1582 (a mutant of parent strain EIP-N1 (CNCM I-1556) isolated from soil in the central plains region of Israel) (International Publication No. 2009 / 126473, U.S. Patent No. 6,406,690; e.g., Votivo® from Bayer CropScience LP, USA), B. pumilus GHA 180 (IDAC 260707-01; e.g., Premier PRO-MIX® BX) from Horticulture, Quebec, Canada; B. pumilus INR-7 (also known as BU-F22 and BU-F33) (NRRL B-50185, NRRL B-50153; U.S. Patent No. 8,445,255) isolated at least before 1993 from cucumbers infected with Erwinia tracheiphila; B. pumilus KFP9F (NRRL B-50754; International Publication No. 2014 / 029697; e.g., BAC-UP or FUSION-P from BASF Agricultural Specialties (Pty) Ltd., South Africa); B. pumilus QST isolated at least before 2008 from the rhizosphere of pasture grasses in South Africa; B. 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 LP, USA), B. simplex (B.B. subtilis FB17 (also known as UD 1022 or UD 10-22) (ATCC PTA-11857; System.Appl.Microbiol.27,372-379,2004; U.S. Patent Application Publication No. 2010 / 0260735; International Publication No. 2011 / 109395), isolated from the roots of red beet in North America; B. thuringiensis ssp. aizawai ABTS-1857 (also known as ABG-6346; ATCC SD-1372), isolated from soil collected from a turf in Ephraim, Wisconsin, USA in 1987; e.g., BioFa XenTari® from AG, Muensingen, Germany; HD-1, identical to Bt subspecies kurstaki (Btssp. kurstaki) ABTS-351 (ATCC SD-1275; e.g., Dipel® DF from Valent BioSciences, IL, USA), isolated in 1967 from black larvae of the cottonweed moth in Brownsville, Texas, USA; Bt subspecies kurstaki (Btssp. kurstaki) SB4 (NRRL B-50753; e.g., Beta from BASF Agricultural Specialties (Pty) Ltd., South Africa), isolated from the carcasses of E. saccharina larvae. Pro(registered trademark), Bt subspecies tenebrionis (Btssp. tenebrionis) NB-176-1 (a mutant of the wild-type strain NB-125, isolated in 1982 from a dead pupa of the beetle Tenebrio molitor) (DSM 5480; European Patent No. 585215B1; e.g., Novodor(registered trademark) from Valent BioSciences, Switzerland), Beauveria bassiana GHA (ATCC 74250; e.g., Laverlam Int. Corp.),BotaniGard® 22WGP from the USA, B. bassiana JW-1 (ATCC 74040; e.g., Naturalis® from CBC (Europe) Srl, Italy), B. bassiana PPRI 5339 (NRRL 50757; e.g., BroadBand® from BASF Agricultural Specialities (Pty) Ltd., South Africa) isolated from the larvae of the tortoise beetle Conchyloctenia punctata, Bradyrhizobium elkanii strain SEMIA 5019 (also called 29W) isolated in Rio de Janeiro, Brazil, and North American isolates from the area where the previous inoculations occurred, Rio Grande do SEMIA 587 (Appl. Environ. Microbiol. 73(8), 2635, 2007; e.g., GELFIX 5 from BASF Agricultural Specialties Ltd., Brazil), isolated in Sul in 1967 and used in commercially available inoculations since 1968; B. japonicum 532c (Nitragin 61A152; Can. J. Plant. Sci. 70, 661-666, 1990; e.g., in Rhizoflo®, Histic®, Hicoat® Super from BASF Agricultural Specialties Ltd., Canada), isolated from a field in Wisconsin, USA; and the USDA 138 strain of B. japonicum E-109 mutant (INTA E109, SEMIA 5085;Eur.J.Soil Biol.45,28-35,2009;Biol.Fertil.Soils 47,81-89,2011);Deposited in SEMIA and known from Appl.Environ.Microbiol.73(8),2635,2007, B. japonicum (B.SEMIA 5079 (CPAC 15; e.g., GELFIX 5 or ADHERE 60 from BASF Agricultural Specialties Ltd., Brazil), isolated by Embrapa-Cerrados from soil in the Cerrados region of Brazil and used in commercially available inoculum since 1992; and SEMIA 586 (CB180), originally isolated in the USA and obtained under laboratory conditions by Embrapa-Cerrados in Brazil and used in commercially available inoculum since 1992. 9) Natural mutants of B. japonicum SEMIA 5080 (CPAC7; e.g., GELFIX 5 or ADHERE 60 from BASF Agricultural Specialties Ltd., Brazil); Burkholderia sp. A396 (NRRL B-50319; International Publication No. 2013 / 032693; Marrone Bio Innovations, Inc., USA), isolated from soil in Nikko, Japan in 2008; Coniothyrium minitans CON / M / 91-08 (International Publication No. 1996 / 021358; DSM 9660; e.g., Contans® WG, Intercept® WG from Bayer CropScience AG, Germany); Harpin (alpha-beta) protein (Science 257, 85-88, 1992; e.g., Messenger (trademark) or HARP-N Tek from Plant Health Care plc, UK), Helicoverpa armigera nuclear polyhedrosis virus (HearNPV) (J. Invertebrate Pathol. 107, 112-126, 2011; e.g., Helicovex (registered trademark) from Adermatt Biocontrol, Switzerland; Diplomata (registered trademark) from Koppert, Brazil; Vivus (registered trademark) Max from AgBiTech Pty Ltd., Queensland, Australia), Helicoverpa zea single capsid nuclear polyhedrosis virus (HzSNPV) (e.g., Gemstar (registered trademark) from Certis LLC, USA), Helicoverpa zea nuclear polyhedrosis virus ABA-NPV-U (e.g., AgBiTech Pty Ltd.Heligen (registered trademark) from Queensland, Australia; Heterorhabditis bacteriophora (e.g., Nemasys (registered trademark) G from BASF Agricultural Specialities Limited, UK); Isaria fumosorosea Apopka-97 (ATCC 20874; Biocontrol Science Technol. 22(7), 747-761, 2012; e.g., PFR-97 (trademark) or PreFeRal (registered trademark) from Certis LLC, USA) isolated from Codlinga in Austria; Metarhizium anisopliae var.Anisopliae) F52 (also known as 275 or V275) (DSM 3884, ATCC 90448; e.g., Met52® Novozymes Biologicals BioAg Group, Canada), Metschnikowia fructicola 277 isolated from grapes in central Israel (U.S. Patent No. 6,994,849; NRRL Y-30752; e.g., former name Shemer® from Agrogreen, Israel), Paecilomyces ilacinus 251 isolated from nematode eggs infected in the Philippines (AGAL 89 / 030550; International Publication No. 1991 / 02051; Crop Protection 27, 352-361, 2008; e.g., Bayer CropScience BioAct® from AG, Germany and MeloCon® from Certis, USA; Paenibacillus alvei NAS6G6 isolated from the rhizosphere of pasture grass in South Africa at least before 2008 (International Publication No. 2014 / 029697; NRRL B-50755; e.g., BAC-UP from BASF Agricultural Specialties (Pty) Ltd., South Africa); Paenibacillus strains isolated from soil samples from various locations in Europe, including Germany: P. epiphyticus Lu17015 (International Publication No. 2016 / 020371; DSM 26971); P. polymyxa subspecies plantarum ssp.plantarum) Lu16774 (International Publication No. 2016 / 020371; DSM 26969), Pp subspecies plantarum (Ppssp.plantarum) strain Lu17007 (International Publication No. 2016 / 020371; DSM 26970); Illinois, USPasteuria nishizawae Pn1 (ATCC SD-5833; Federal Register 76(22), 5808, February 2, 2011; e.g., Clariva (trademark) PN from Syngenta Crop Protection, LLC, USA), originally isolated from a soybean field in A, Canada; and Penicillium bilaiae (also known as P. bilaii) strains ATCC 18309 (=ATCC 74319), ATCC 20851 and / or ATCC 22348 (=ATCC 74318) (Fertilizer Res. 39, 97-103, 1994; Can. J. Plant) Sci.78(1),91-102,1998; US Patent No. 5,026,417, International Publication No. 1995 / 017806; e.g., JumpStart®, Provide® from Novozymes Biologicals BioAg Group, Canada), Japanese knotweed (Reynoutria sachalinensis) extract (European Patent No. 0307510B1; e.g., Regalia® SC from Marrone BioInnovations, Davis, CA, USA or Milsana® from BioFa AG, Germany), Steinernema carpocapsae (e.g., Millennium® from BASF Agricultural Specialties Limited, UK), S. feltiae (e.g., BioWorks, Inc.)Nemashield (registered trademark) from the USA; Nemasys (registered trademark) from BASF Agricultural Specialities Limited, UK; Streptomyces microflavus NRRL B-50550 (International Publication No. 2014 / 124369; Bayer CropScience, Germany); Trichoderma asperelloides JM41R (NRRL 50759; also known as T. fertile; e.g., Trichoplus (registered trademark) from BASF Agricultural Specialities (Pty) Ltd., South Africa), T. harzianum T-22 (also known as KRL-AG2) (ATCC 20847; BioControl 57, 687-696, 2012; e.g., BioWorks) Plantshield® (registered trademark) from Advanced Biological Marketing Inc., USA, or SabrEx® (trademark) from Advanced Biological Marketing Inc., Van Wert, OH, USA.

[0330] According to another embodiment of the mixture, at least one of the pesticides II is from group L1) to L5): L1) Microbial pesticides having fungicidal, bactericidal, virucidal and / or plant defense activating activity: Aureobasidium pullulans DSM 14940 and DSM 14941 (L1.1), Bacillus amyloliquefaciens AP-188 (L.1.2), B. amyloliquefaciens ssp. plantarum D747 (L.1.3), B. amyloliquefaciens ssp. plantarum FZB24 (L.1.4), B. amyloliquefaciens ssp. plantarum B. amyloliquefaciens ssp.plantarum) FZB42 (L.1.5), B. amyloliquefaciens ssp.plantarum) MBI600 (L.1.6), B. amyloliquefaciens ssp.plantarum) QST-713 (L.1.7), B. amyloliquefaciens ssp.plantarum) TJ1000 (L.1.8), B. pumilus GB34 (L.1.9), B. pumilus GHA 180 (L.1.10), B. pumilus INR-7 (L.1.11), B. pumilus KFP9F (L.1.12), B. pumilus QST 2808 (L.1.13), B. simplex ABU 288 (L.1.14), B. subtilis FB17 (L.1.15), Coniothyrium minitans CON / M / 91-08 (L.1.16), Metschnikowia fructicola NRRL Y-30752 (L.1.17), Paenibacillus albei alvei)NAS6G6(L.1.18), P.P. epiphyticus Lu17015 (L.1.25), P. polymyxa ssp. plantarum Lu16774 (L.1.26), Pp ssp. plantarum strain Lu17007 (L.1.27), Penicillium bilaiae ATCC 22348 (L.1.19), P. bilaiae ATCC 20851 (L.1.20), Penicillium bilaiae ATCC 18309 (L.1.21), Streptomyces microflavus NRRL B-50550 (L.1.22), Trichoderma asperelloides JM41R (L.1.23), T. harzianum T-22 (L.1.24); L2) Biochemical pesticides having fungicidal, bactericidal, virucidal, and / or plant defense activating activity: Harpin protein (L.2.1), Reynoutria sachalinensis extract (L.2.2); L3) Microbial pesticides having insecticidal activity, acaricidal activity, molluscicidal activity and / or nematicidal activity: Bacillus firmus I-1582 (L.3.1), B. thuringiensis ssp. aizawai ABTS-1857 (L.3.2), Bt ssp. kurstaki ABTS-351 (L.3.3), Bt ssp. kurstaki SB4 (L.3.4), Bt ssp. tenebrionis NB-176-1 (L.3.5), Beauveria bassiana Bassiana GHA (L.3.6), B. bassiana JW-1 (L.3.7), B. bassiana PPRI 5339 (L.3.8), Burkholderia sp. A396 (L.3.9), Helicoverpa armigera nucleopolyhedrovirus (HearNPV) (L.3.10), Helicoverpa zea nucleopolyhedrovirus (HzNPV) ABA-NPV-U (L.3.11), Helicoverpa zea single capsid nucleopolyhedrovirus) (HzSNPV) (L.3.12), Heterohabditis bacteriophora (L.3.13), Isaria fumosorosea Apopka-97 (L.3.14), Metarhizium anisopliae var. anisopliae F52 (L.3.15), Paecilomyces lilacinus 251 (L.3.16), Pasteuria nishizawae Pn1 (L.3.17) Steinernema carpocapsae (L.3.18), S. feltiae (L.3.19); L4) Biochemical pesticides having insecticidal activity, acaricidal activity, molluscicidal activity, pheromone activity and / or nematicidal activity: cis-jasmon (L.4.1), methyl jasmonate (L.4.2), quillaja extract (L.4.3); L5) Microbial pesticides having plant stress reduction activity, plant growth regulator activity, plant growth promoting activity and / or yield increasing activity: Azospirillum brasilense Ab-V5 and Ab-V6 (L.5.1), A. Brasilense Sp245 (L.5.2), Bradyrhizobium elkanii SEMIA 587 (L.5.3), B. elkanii SEMIA 5019 (L.5.4), B. japonicum 532c (L.5.5), B. japonicum E-109 (L.5.6), B. japonicum SEMIA 5079 (L.5.7), B. japonicum SEMIA 5080 (L.5.8) Selected from.

[0331] The present invention further relates to a pesticide composition comprising a mixture of at least one compound I (component 1), at least one bio-pesticide (component 2) selected from group L) as described above, particularly at least one bio-pesticide selected from group L1) and group L2), and optionally at least one suitable auxiliary agent.

[0332] The present invention further relates to a pesticide composition comprising a mixture of at least one compound I (component 1), at least one bio-pesticide (component 2) selected from group L) as described above, particularly at least one bio-pesticide selected from groups L3) and L4), and optionally at least one suitable auxiliary agent.

[0333] As the biological agent II (component 2), a component selected from the groups L1), L3), and L5) is preferably (L.1.2), (L.1.3), (L.1.4), (L.1.5), (L.1.6), (L.1.7), (L.1.8), (L.1.10), (L.1.11), (L.1.12), (L.1.13), (L.1.14), (L .1.15), (L.1.17), (L.1.18), (L.1.19), (L.1.20), (L.1.21), (L.1.25), (L.1.26), (L. 1.27), (L.3.1); (L.3.9), (L.3.16), (L.3.17), (L.5.1), (L.5.2), (L.5.3), (L.5.4), (L (L.5.5), (L.5.6), (L.5.7), (L.5.8); (L.4.2) and (L.4.1) are selected from the above strains; more preferably (L.1.2), (L.1.6), (L.1.7), (L.1.8), (L.1.11), (L.1.12), (L.1.13), (L.1.14), (L.1.15) Mixtures containing biopesticides selected from (L.1.18), (L.1.19), (L.1.20), (L.1.21), (L.3.1); (L.3.9), (L.3.16), (L.3.17), (L.5.1), (L.5.2), (L.5.5), (L.5.6); (L.4.2) and (L.4.1) are also preferred. These mixtures are particularly suitable for the treatment of reproductive materials, i.e., seed treatment, and similarly, particularly suitable for soil treatment. These seed treatment mixtures are particularly suitable for crops such as grains, maize, and legumes such as soybeans.

[0334] As the biological agent II (component 2), a component selected from the groups L1), L3), and L5) is preferably (L1.1), (L1.2), (L1.3), (L1.6), (L1.7), (L1.9), (L1.11), (L1.12), (L1.13), (L1.14), (L1.15), (L1.1) .17), (L.1.18), (L.1.22), (L.1.23), (L.1.24), (L.1.25), (L.1.26), (L.1.27), (L .2.2);(L.3.2), (L.3.3), (L.3.4), (L.3.5), (L.3.6), (L.3.7), (L.3.8), (L.3.10) A mixture containing a biocide selected from the strains shown above as (L.3.11), (L.3.12), (L.3.13), (L.3.14), (L.3.15), (L.3.18), (L.3.19); and (L.4.2) is also preferred. These mixtures are particularly suitable for foliar treatment of cultivated plants, preferably vegetables, fruits, vines, grains, corn, and leguminous crops such as soybeans.

[0335] A composition containing a mixture of active ingredients can be prepared by conventional means, for example, the means shown with respect to the composition of compound I.

[0336] When living microorganisms, such as pesticides II from groups L1), L3), and L5), form part of a composition, such compositions can be prepared by conventional means (e.g., HDBurges: Formulation of Microbial Biopesticides, Springer, 1998; International Publication No. 2008 / 002371, U.S. Patent No. 6,955,912, U.S. Patent No. 5,422,107). [Examples]

[0337] I. Synthesis Examples Example 1: 5-(6-(difluoromethyl)-5-methylpyridine-3-yl)-9-fluoro-2,2-dimethyl-2,3-dihydrobenzo[f][1,4]thiazepine 1,1-dioxide Step 1: Preparation of (6-(difluoromethyl)-5-methylpyridine-3-yl)(2,3-difluorophenyl)methanol To a solution of 1,2-difluoro-3-iodobenzene (16.8 g, 0.07 mol) in THF (150 mL), i-PrMgCl (2 M) (36 mL, 0.073 mol) was added at 0°C under N2, and the mixture was stirred at 0°C for 30 minutes. Then, 6-(difluoromethyl)-5-methylnicotinaldehyde (10 g, 0.058 mol) in THF was added at 0°C, and the mixture was stirred at 0-20°C under N2 for 4 hours. TLC (PE:HCl = 3:1) indicated that the reaction was complete. The reaction mixture was quenched with aqueous NH4Cl solution (200 mL), extracted with HCl (150 mL), and washed with brine (200 mL). The organic layer was dried over Na2SO4 and concentrated to obtain (6-(difluoromethyl)-5-methylpyridine-3-yl)(2,3-difluorophenyl)methanol (16.7 g, crude) as a yellow solid. The title compound was used without further purification. 1 H NMR(400MHz,CDCl3)δ [ppm]=8.38(s,1H)7.54(s,1H)7.20-7.25(m,1H)7.02-7.09(m,2H)6.45-6.75(m,1H)6.14(s,1H)2.40-2.44(m,3H).

[0338] Step 2: Preparation of (6-(difluoromethyl)-5-methylpyridine-3-yl)(2,3-difluorophenyl)methanone To a solution of (6-(difluoromethyl)-5-methylpyridine-3-yl)(2,3-difluorophenyl)methanol (16.7 g, 0.059 mol) in THF (200 mL), MnO2 (51 g, 0.59 mol) was added, and the mixture was stirred at 80°C for 16 hours. TLC (PE:HCl=3:1) indicated that the reaction was complete. The reaction mixture was filtered, the filtrate was concentrated, and purified by column chromatography (PE:HCl=7:1) to obtain (6-(difluoromethyl)-5-methylpyridine-3-yl)(2,3-difluorophenyl)methanone (12.5 g, 75%) as a yellow oil. The title compound was used without further purification. 1 H NMR(400MHz,CDCl3)δ [ppm]=8.69(s,1H)7.95(s,1H)7.27-7.41(m,2H)7.19-7.24(m,1H)6.49-6.84(m,1H)2.53(s,3H).

[0339] Step 3: 5-(6-(difluoromethyl)-5-methylpyridine-3-yl)-9-fluoro-2,2-dimethyl-2,3-dihydrobenzo[f][1,4]thiazepine To a solution of (6-(difluoromethyl)-5-methylpyridine-3-yl)(2,3-difluorophenyl)methanone (1 g, 3.53 mmol) and 1-amino-2-methylpropane-2-thiol hydrochloride (751 mg, 5.30 mmol) in DMF (20 mL), Cs2CO3 (3.45 g, 10.60 mmol) was added at 25°C under N2. The mixture was then stirred at 40°C for 2 hours. TLC (PE:HCl = 3:1) indicated that the reaction was complete. The reaction mixture was quenched in H2O (15 mL) and extracted with HCl (10 mL x 3). The organic phase was washed with brine (10 mL x 2), dried over Na2SO4, and concentrated. The residue was purified by column chromatography (PE:siRNA=7:1) to obtain 5-(6-(difluoromethyl)-5-methylpyridine-3-yl)-9-fluoro-2,2-dimethyl-2,3-dihydrobenzo[f][1,4]thiazepine (1.1 g, yield: 88.9%) as a yellow solid. 1H NMR(400MHz,MeOD)δ [ppm]=8.45(s,1H),7.80(s,1H),7.43(td,J=7.91,5.19Hz,1H),7.26(t,J=8.32Hz,1 H),6.93(d,J=7.63Hz,1H),6.62-6.90(m,1H),3.21(s,2H),2.41(s,3H),1.39(s,6H)

[0340] Step 4: 5-(6-(difluoromethyl)-5-methylpyridine-3-yl)-9-fluoro-2,2-dimethyl-2,3-dihydrobenzo[f][1,4]thiazepine 1-oxide A solution of 5-(6-(difluoromethyl)-5-methylpyridine-3-yl)-9-fluoro-2,2-dimethyl-2,3-dihydrobenzo[f][1,4]thiazepine (300 mg, 0.86 mmol) in EtOH (3 mL) is prepared by adding (NH4)6Mo7O 24 4H2O (498 mg, 0.43 mmol) and H2O2 (30%, 300 mg, 0.86 mmol) were added under N2 conditions at 25°C, and the mixture was stirred at 25°C for 16 hours. LC-MS indicated that the reaction was complete. The reaction mixture was quenched in H2O (5 mL), and the pH was adjusted to 7-8 with approximately 10% NaHCO3 aqueous solution. Then, Na2SO3 aqueous solution (20 mL) was added to the resulting solution, extracted with siRNA (3 mL x 3), washed with brine (3 mL x 2), and dried over Na2SO4 to concentrate. The residue was purified by column chromatography (PE:siRNA = 3:1 to 1:1) to obtain 5-(6-(difluoromethyl)-5-methylpyridine-3-yl)-9-fluoro-2,2-dimethyl-2,3-dihydrobenzo[f][1,4]thiazepine-1-oxide (230 mg, yield: 74%) as a yellow solid. 1H NMR(400MHz,MeOD)δ [ppm]=8.58(d,J=1.00Hz,1H),7.89(s,1H),7.76-7.82(m,1H),7.49-7.54(m,1H),7.21(dd,J=7.63,0.63Hz,1H ),6.72-6.99(m,1H),4.02(d,J=11.13Hz,1H),3.36(d,J=11.13Hz,1H),2.51(s,3H),1.66(s,3H),1.27(s,3H).

[0341] Step 5: 5-(6-(difluoromethyl)-5-methylpyridine-3-yl)-9-fluoro-2,2-dimethyl-2,3-dihydrobenzo[f][1,4]thiazepine 1,1-dioxide A solution of 5-(6-(difluoromethyl)-5-methylpyridine-3-yl)-9-fluoro-2,2-dimethyl-2,3-dihydrobenzo[f][1,4]thiazepine (420 mg, 1.20 mmol) in EtOH (5 mL) is prepared by adding (NH4)6Mo7O 24 4H2O (698 mg, 0.60 mmol) and H2O2 (30%, 1.36 g, 11.99 mmol) were added under N2 conditions at 25°C. The mixture was stirred at 25°C for 16 hours. LC-MS indicated that the reaction was complete. The reaction mixture was quenched in H2O (5 mL) and the pH was adjusted to 7-8 with approximately 10% NaHCO3 aqueous solution. Then, Na2SO3 aqueous solution (20 mL) was added to the resulting solution, extracted with siRNA (5 mL x 3), washed with brine (5 mL x 2), and dried over Na2SO4 to concentrate. The residue was purified by preparative HPLC to obtain 5-(6-(difluoromethyl)-5-methylpyridine-3-yl)-9-fluoro-2,2-dimethyl-2,3-dihydrobenzo[f][1,4]thiazepine 1,1-dioxide (200 mg, yield: 43.5%) as a yellow solid.

[0342] The compounds listed in Table I were prepared using similar methods.

[0343] Table I:R 2 , R 3 , R 5 , R 6 , R7 , R 8 , R 9 Compounds Ex-1 to Ex-92 of formula I, where the meaning of Xn is as defined in each row.

[0344] LCMS: Liquid Chromatography Mass Spectrometry; HPLC - Shimadzu Nexera LC-30 LCMS-2020 (ESI+) using a Kinetex XB C18 1.7μ (50×2.1mm) column; Elutate: Acetonitrile / Water + 0.1% Trifluoroacetic Acid (5:95 to 100:0 gradient over 1.5 minutes at 60°C, with a flow gradient of 0.8 to 1.0 mL / min over 1.5 minutes).

[0345] **LCMS: Liquid Chromatography Mass Spectrometry; HPLC - Shimadzu Nexera LC-30 LCMS-2020 (ESI+) using LUX Cellulose-1 column 5μm (150×4.6mm); Eluten: Acetonitrile / Water + 0.1% Formic Acid (50:50 to 100:0 gradient, flow rate 0.6mL / min, 10 minutes at 40°C).**

[0346] ***LCMS: Liquid Chromatography Mass Spectrometry; HPLC - Shimadzu LCMS DELIVER-220 (ESI+) using Luna-C18 column (30mm × 2.0mm × 3μm particles); Eluten: Acetonitrile (+0.02% TFA) / Water (+0.04%) (5:95 to 95:5 gradient over 1.5 minutes at 40°C, flow gradient of 0.8 to 0.8 mL / min over 3 minutes).

[0347] R t : Holding time in minutes. [ka]

[0348] [Table 42]

[0349] [Table 43]

[0350] Table 44

[0351] Table 45

[0352] Table 46

[0353] Table 47

[0354] Table 48

[0355] Table 49

[0356] Table 50

[0357] Table 51

[0358] Table 52

[0359] Table 53

[0360] Microtest The active compound was separately formulated as a stock solution at a concentration of 10,000 ppm in dimethyl sulfoxide.

[0361] Example 1 - Activity against Botrytis cinerea, a gray mold fungus, in a microtiter plate test. The stock solutions were mixed according to the specified ratio, pipetted onto a microtiter plate (MTP), and diluted with water to the specified concentration. Next, a spore suspension of Botruci cinerea in biomalt or yeast-bacto-peptone-sodium acetate aqueous solution was added. The plate was placed in a steam-saturated chamber at 18°C. Using an absorption spectrometer, the MTP was measured at 405 nm for 7 days after inoculation.

[0362] In this test, samples treated with 31 ppm of the active substance according to Example Ex-1 showed 0% pathogen growth.

[0363] Furthermore, in this test, samples treated with 31 ppm of the active substance according to Examples Ex-57, Ex-58, Ex-60, Ex-61, Ex-63, Ex-64, Ex-65, Ex-66, Ex-67, Ex-68, Ex-69, Ex-70, Ex-71, Ex-72, Ex-73, Ex-74, Ex-75, Ex-76, Ex-77, Ex-78, Ex-79, Ex-80, Ex-81, Ex-82, Ex-83, Ex-84, and Ex-85 showed a maximum pathogen growth of 24%.

[0364] Example 2 - Activity against wheat leaf blight caused by Septoria tritici in a microtiter plate test. The active compound was separately formulated as a stock solution at a concentration of 10,000 ppm in dimethyl sulfoxide. The stock solutions were mixed in the appropriate proportions, pipetted onto a microtiter plate (MTP), and diluted with water to the specified concentration. Then, a spore suspension of Septorion tritici in biomalt, yeast-bacto-peptone-glycerin, or DOB aqueous solution was added.

[0365] In this test, samples treated with 31 ppm of the active substance according to Example Ex-1 showed 9% pathogen growth.

[0366] Furthermore, in this test, samples treated with 31 ppm of the active substance according to Examples Ex-61, Ex-68, Ex-72, Ex-73, and Ex-78 showed a maximum pathogen growth of 21%.

[0367] Example 3 - Activity against Fusarium culmorum in microtiter plate tests. The stock solutions were mixed according to the specified ratio, pipetted onto a microtiter plate (MTP), and diluted with water to the specified concentration. Next, a spore suspension of Fusarium culmorum in biomalt or yeast-bacto-peptone-sodium acetate aqueous solution was added. The plate was placed in a steam-saturated chamber at 18°C. Using an absorption spectrometer, the MTP was measured at 405 nm for 7 days after inoculation.

[0368] In this test, samples treated with 31 ppm of the active substance according to Examples Ex-57, Ex-60, Ex-63, Ex-64, Ex-68, Ex-70, Ex-71, Ex-72, Ex-74, Ex-75, and Ex-80 showed a maximum pathogen growth of 22%.

[0369] Example 4 - Activity against Alternaria alternata in microtiter plate testing The stock solutions were mixed according to the specified ratio, pipetted onto a microtiter plate (MTP), and diluted with water to the specified concentration. Next, a spore suspension of Alternaria alternata in biomalt or yeast-bacto-peptone-sodium acetate aqueous solution was added. The plate was placed in a steam-saturated chamber at 18°C. Using an absorption spectrometer, the MTP was measured at 405 nm for 7 days after inoculation.

[0370] In this test, samples treated with 31 ppm of the active substance according to Examples Ex-1, Ex-2, Ex-3, Ex-10, Ex-11, Ex-16, Ex-19, Ex-20, Ex-25, Ex-26, Ex-29, Ex-31, Ex-33, Ex-39, Ex-40, Ex-41, Ex-45, Ex-46, Ex-48, Ex-49, Ex-50, Ex-51, and Ex-52 showed a maximum pathogen growth of 13%.

[0371] Example 5 - Activity against Alternaria solani in a microtiter plate test. The stock solutions were mixed according to the specified ratio, pipetted onto a microtiter plate (MTP), and diluted with water to the specified concentration. Next, a spore suspension of Alternaria solani in biomalt or yeast-bacto-peptone-sodium acetate aqueous solution was added. The plate was placed in a steam-saturated chamber at 18°C. Using an absorption spectrometer, the MTP was measured at 405 nm for 7 days after inoculation.

[0372] In this test, samples treated with 31 ppm of the active substance according to Examples Ex-1, Ex-2, Ex-3, Ex-10, Ex-11, Ex-16, Ex-19, Ex-20, Ex-25, Ex-26, Ex-29, Ex-31, Ex-33, Ex-39, Ex-40, Ex-41, Ex-45, Ex-48, Ex-49, Ex-50, Ex-51, and Ex-52 showed a maximum pathogen growth of 12%.

[0373] Example 6 - Activity against Cochliobolus sativus in microtiter plate testing The stock solutions were mixed according to the specified ratio, pipetted onto a microtiter plate (MTP), and diluted with water to the specified concentration. Next, a spore suspension of Cochliobolus sativus in biomalt or yeast-bacto-peptone-sodium acetate aqueous solution was added. The plate was placed in a steam-saturated chamber at 18°C. Using an absorption spectrometer, the MTP was measured at 405 nm for 7 days after inoculation.

[0374] In this test, samples treated with 31 ppm of the active substance according to Examples Ex-1, Ex-2, Ex-3, Ex-10, Ex-11, Ex-16, Ex-19, Ex-20, Ex-23, Ex-24, Ex-25, Ex-26, Ex-29, Ex-31, Ex-33, Ex-39, Ex-40, Ex-41, Ex-45, Ex-46, Ex-48, Ex-49, Ex-50, Ex-51, and Ex-52 showed a maximum pathogen growth of 19%.

[0375] Example 7 - Activity of Cercospora beticula in a microtiter plate test The stock solutions were mixed according to the specified ratio, pipetted onto a microtiter plate (MTP), and diluted with water to the specified concentration. Next, a spore suspension of Cercospora beticula in biomalt or yeast-bacto-peptone-sodium acetate aqueous solution was added. The plate was placed in a steam-saturated chamber at 18°C. Using an absorption spectrometer, the MTP was measured at 405 nm for 7 days after inoculation.

[0376] In this test, samples treated with 31 ppm of the active substance according to Examples Ex-2, Ex-3, Ex-10, Ex-11, Ex-16, Ex-25, Ex-41, Ex-48, Ex-49, Ex-50, Ex-51, and Ex-52 showed a maximum pathogen growth of 13%.

[0377] Example 8 - Activity of Cercospora sojina in a microtiter plate test The stock solutions were mixed according to the specified ratio, pipetted onto a microtiter plate (MTP), and diluted with water to the specified concentration. Next, a spore suspension of Cercospora sojina in biomalt or yeast-bacto-peptone-sodium acetate aqueous solution was added. The plate was placed in a steam-saturated chamber at 18°C. Using an absorption spectrometer, the MTP was measured at 405 nm for 7 days after inoculation.

[0378] In this test, samples treated with 31 ppm of the active substance according to Examples Ex-1, Ex-2, Ex-10, Ex-11, Ex-16, Ex-19, Ex-20, Ex-23, Ex-24, Ex-25, Ex-31, Ex-41, Ex-47, Ex-48, Ex-49, Ex-50, Ex-51, and Ex-52 showed a maximum pathogen growth of 18%.

[0379] Example 9 - Activity of Cercospora zea maydis in microtiter plate testing. The stock solutions were mixed according to the specified ratio, pipetted onto a microtiter plate (MTP), and diluted with water to the specified concentration. Next, a spore suspension of Cercospora zea maydis in biomalt or yeast-bacto-peptone-sodium acetate aqueous solution was added. The plate was placed in a steam-saturated chamber at 18°C. Using an absorption spectrometer, the MTP was measured at 405 nm for 7 days after inoculation.

[0380] In this test, samples treated with 31 ppm of the active substance according to Examples Ex-1, Ex-2, Ex-10, Ex-11, Ex-16, Ex-20, Ex-25, Ex-31, Ex-38, Ex-40, Ex-45, and Ex-52 showed a maximum pathogen growth of 18%.

[0381] Example 10 - Activity against Colletotrichum orbiculare in a microtiter plate test. The stock solutions were mixed according to the specified ratio, pipetted onto a microtiter plate (MTP), and diluted with water to the specified concentration. Next, a spore suspension of Colletotrichum orbiculare in biomalt or yeast-bacto-peptone-sodium acetate aqueous solution was added. The plate was placed in a steam-saturated chamber at 18°C. Using an absorption spectrometer, the MTP was measured at 405 nm for 7 days after inoculation.

[0382] In this test, samples treated with 31 ppm of the active substance according to Examples Ex-1, Ex-2, Ex-3, Ex-4, Ex-5, Ex-7, Ex-8, Ex-9, Ex-10, Ex-11, Ex-13, Ex-14, Ex-15, Ex-16, Ex-19, Ex-20, Ex-23, Ex-25, Ex-26, Ex-27, Ex-28, Ex-29, Ex-30, Ex-31, Ex-33, Ex-34, Ex-35, Ex-36, Ex-38, Ex-39, Ex-40, Ex-41, Ex-42, Ex-43, Ex-44, Ex-45, Ex-46, Ex-48, Ex-49, Ex-50, Ex-51, and Ex-52 showed a maximum pathogen growth of 18%.

[0383] Example 11 - Activity of Corynespora cassiicola-resistant isolate (G143A) in microtiter plate testing. The stock solutions were mixed according to the specified ratio, pipetted onto a microtiter plate (MTP), and diluted with water to the specified concentration. Next, a spore suspension of Corynespora cassiicola-resistant isolate (G143A) in biomalt or yeast-bacto-peptone-sodium acetate aqueous solution was added. The plate was placed in a steam-saturated chamber at 18°C. Using an absorption spectrometer, the MTP was measured at 405 nm for 7 days after inoculation.

[0384] In this test, samples treated with 31 ppm of the active substance according to Examples Ex-1, Ex-2, Ex-3, Ex-10, Ex-11, Ex-16, Ex-19, Ex-25, Ex-41, Ex-45, Ex-46, Ex-48, Ex-49, Ex-50, Ex-51, and Ex-52 showed a maximum pathogen growth of 17%.

[0385] Example 12 - Activity of Fusarium graminearum in microtiter plate tests The stock solutions were mixed according to the specified ratio, pipetted onto a microtiter plate (MTP), and diluted with water to the specified concentration. Next, a suspension of Fusarium graminearum spores in biomalt or yeast-bacto-peptone-sodium acetate aqueous solution was added. The plate was placed in a steam-saturated chamber at 18°C. Using an absorption spectrometer, the MTP was measured at 405 nm for 7 days after inoculation.

[0386] In this test, samples treated with 31 ppm of the active substance according to Examples Ex-10, Ex-11, Ex-16, Ex-19, Ex-20, Ex-31, Ex-48, Ex-49, Ex-50, Ex-51, and Ex-52 showed a maximum pathogen growth of 14%.

[0387] Example 13 - Activity of Leptosphaerium nodorum in a microtiter plate test The stock solutions were mixed according to the specified ratio, pipetted onto a microtiter plate (MTP), and diluted with water to the specified concentration. Next, a spore suspension of Leptosphaerium nodorum in biomalt or yeast-bacto-peptone-sodium acetate aqueous solution was added. The plate was placed in a steam-saturated chamber at 18°C. Using an absorption spectrometer, the MTP was measured at 405 nm for 7 days after inoculation.

[0388] In this test, samples treated with 31 ppm of the active substance according to Examples Ex-1, Ex-2, Ex-3, Ex-5, Ex-7, Ex-10, Ex-11, Ex-16, Ex-19, Ex-20, Ex-22, Ex-23, Ex-25, Ex-26, Ex-29, Ex-31, Ex-33, Ex-39, Ex-40, Ex-41, Ex-45, Ex-46, Ex-47, Ex-48, Ex-49, Ex-50, Ex-51, and Ex-52 showed a maximum pathogen growth of 18%.

[0389] Example 14 - Activity of Microdochium nivale in a microtiter plate test The stock solutions were mixed according to the specified ratio, pipetted onto a microtiter plate (MTP), and diluted with water to the specified concentration. Next, a spore suspension of Microdochium nivale in biomalt or yeast-bacto-peptone-sodium acetate aqueous solution was added. The plate was placed in a steam-saturated chamber at 18°C. Using an absorption spectrometer, the MTP was measured at 405 nm for 7 days after inoculation.

[0390] In this test, samples treated with 31 ppm of the active substance according to Examples Ex-1, Ex-2, Ex-3, Ex-10, Ex-11, Ex-16, Ex-19, Ex-20, Ex-23, Ex-24, Ex-25, Ex-26, Ex-29, Ex-31, Ex-33, Ex-34, Ex-35, Ex-39, Ex-40, Ex-41, Ex-42, Ex-43, Ex-45, Ex-46, Ex-47, Ex-48, Ex-49, Ex-50, Ex-51, and Ex-52 showed a maximum pathogen growth of 14%.

[0391] Example 15 - Activity of Monilinia laxa in microtiter plate testing The stock solutions were mixed according to the specified ratio, pipetted onto a microtiter plate (MTP), and diluted with water to the specified concentration. Then, a spore suspension of Monilinia laxa in biomalt or yeast-bacto-peptone-sodium acetate aqueous solution was added. The plate was placed in a steam-saturated chamber at 18°C. Using an absorption spectrometer, the MTP was measured at 405 nm for 7 days after inoculation.

[0392] In this test, samples treated with 31 ppm of the active substance according to Examples Ex-1, Ex-2, Ex-3, Ex-4, Ex-5, Ex-6, Ex-7, Ex-8, Ex-9, Ex-10, Ex-11, Ex-12, Ex-13, Ex-14, Ex-15, Ex-16, Ex-19, Ex-20, Ex-23, Ex-24, Ex-25, Ex-26, Ex-27, Ex-28, Ex-29, Ex-31, Ex-33, Ex-37, Ex-38, Ex-39, Ex-40, Ex-41, Ex-42, Ex-44, Ex-45, Ex-46, Ex-37, Ex-48, Ex-49, Ex-50, Ex-51, and Ex-52 showed a maximum pathogen growth of 15%.

[0393] Example 16 - Activity against Leptosphaeria maculans in a microtiter plate test The stock solutions were mixed according to the specified ratio, pipetted onto a microtiter plate (MTP), and diluted with water to the specified concentration. Then, a spore suspension of Leptosphaeria maculans in biomalt or yeast-bacto-peptone-sodium acetate aqueous solution was added. The plate was placed in a steam-saturated chamber at 18°C. Using an absorption spectrometer, the MTP was measured at 405 nm for 7 days after inoculation.

[0394] In this test, samples treated with 31 ppm of the active substance according to Examples Ex-1, Ex-2, Ex-3, Ex-10, Ex-11, Ex-12, Ex-13, Ex-16, Ex-19, Ex-20, Ex-25, Ex-26, Ex-29, Ex-31, Ex-33, Ex-36, Ex-40, Ex-41, Ex-42, Ex-45, Ex-46, Ex-47, Ex-48, Ex-49, Ex-50, Ex-51, and Ex-52 showed a maximum pathogen growth of 13%.

[0395] Example 17 - Activity of Pyrenophora teres-resistant isolate (F129L) in microtiter plate testing. The stock solutions were mixed according to the specified ratio, pipetted onto a microtiter plate (MTP), and diluted with water to the specified concentration. Next, a spore suspension of Pyrenophora teres-resistant isolate (F129L) in biomalt or yeast-bacto-peptone-sodium acetate aqueous solution was added. The plate was placed in a steam-saturated chamber at 18°C. The MTP was measured at 405 nm using an absorption spectrometer for 7 days after inoculation.

[0396] In this test, samples treated with 31 ppm of the active substance according to Examples Ex-1, Ex-2, Ex-3, Ex-5, Ex-7, Ex-10, Ex-11, Ex-12, Ex-14, Ex-16, Ex-19, Ex-20, Ex-24, Ex-25, Ex-26, Ex-29, Ex-31, Ex-33, Ex-34, Ex-35, Ex-36, Ex-39, Ex-42, Ex-43, and Ex-44 showed a maximum of 20% pathogen growth.

[0397] Example 18 - Activity against Rhizoctonia solani in a microtiter plate test. The stock solutions were mixed according to the specified ratio, pipetted onto a microtiter plate (MTP), and diluted with water to the specified concentration. Next, a spore suspension of Rhizoctonia solani-resistant isolate (F129L) in biomalt or yeast-bacto-peptone-sodium acetate aqueous solution was added. The plate was placed in a steam-saturated chamber at 18°C. Using an absorption spectrometer, the MTP was measured at 405 nm for 7 days after inoculation.

[0398] In this test, samples treated with 31 ppm of the active substance according to Example Ex-41 showed a maximum pathogen growth of 18%.

[0399] Example 19 - Activity against Pyricularia oryzae in a microtiter plate test The stock solutions were mixed according to the specified ratio, pipetted onto a microtiter plate (MTP), and diluted with water to the specified concentration. Next, a spore suspension of Pyricularia oryzae in biomalt or yeast-bacto-peptone-sodium acetate aqueous solution was added. The plate was placed in a steam-saturated chamber at 18°C. Using an absorption spectrometer, the MTP was measured at 405 nm for 7 days after inoculation.

[0400] In this test, Examples Ex-1, Ex-2, Ex-3, Ex-4, Ex-5, Ex-6, Ex-7, Ex-8, Ex-9, Ex-10, Ex-11, Ex-12, Ex-13, Ex-14, Ex-15, Ex-16, Ex-19, Ex-20, Ex-23, Ex-24, Ex-25, Ex-26, Ex-27, Ex-28, Ex-29, Ex-30, Ex Samples treated with 31 ppm of the active substance -31, Ex-33, Ex-34, Ex-35, Ex-36, Ex-37, Ex-38, Ex-39, Ex-40, Ex-41, Ex-43, Ex-44, Ex-45, Ex-46, Ex-47, Ex-48, Ex-49, Ex-50, Ex-51, and Ex-52 showed a maximum pathogen growth of 17%.

[0401] Example 20 - Activity of Stemphylium sp. in microtiter plate testing The stock solutions were mixed according to the specified ratio, pipetted onto a microtiter plate (MTP), and diluted with water to the specified concentration. Next, a spore suspension of Stemphylium sp. in biomalt or yeast-bacto-peptone-sodium acetate aqueous solution was added. The plate was placed in a steam-saturated chamber at 18°C. Using an absorption spectrometer, the MTP was measured at 405 nm for 7 days after inoculation.

[0402] In this test, samples treated with 31 ppm of the active substance according to Examples Ex-1, Ex-2, Ex-3, Ex-10, Ex-11, Ex-16, Ex-19, Ex-20, Ex-25, Ex-26, Ex-29, Ex-31, Ex-33, Ex-36, Ex-37, Ex-40, Ex-41, Ex-42, Ex-46, Ex-47, Ex-49, Ex-50, Ex-51, and Ex-52 showed a maximum pathogen growth of 14%.

[0403] Example 21 - Activity of Ustilago maydis in microtiter plate testing The stock solutions were mixed according to the specified ratio, pipetted onto a microtiter plate (MTP), and diluted with water to the specified concentration. Next, a spore suspension of Ustilago maydis in biomalt or yeast-bacto-peptone-sodium acetate aqueous solution was added. The plate was placed in a steam-saturated chamber at 18°C. Using an absorption spectrometer, the MTP was measured at 405 nm for 7 days after inoculation.

[0404] In this test, samples treated with 31 ppm of the active substance according to Examples Ex-47 and Ex-48 showed a maximum of 6% pathogen growth.

[0405] Example 22 - Activity of Phytophthora infestans in a microtiter plate test. The stock solutions were mixed according to the specified ratio, pipetted onto a microtiter plate (MTP), and diluted with water to the specified concentration. Next, a spore suspension of Phytophthora infestans in biomalt or yeast-bacto-peptone-sodium acetate aqueous solution was added. The plate was placed in a steam-saturated chamber at 18°C. Using an absorption spectrometer, the MTP was measured at 405 nm for 7 days after inoculation.

[0406] In this test, samples treated with 31 ppm of the active substance according to Examples Ex-1, Ex-2, Ex-10, Ex-19, Ex-20, Ex-23, Ex-25, Ex-29, Ex-31, Ex-33, Ex-42, Ex-47, Ex-48, and Ex-52 showed a maximum pathogen growth of 18%.

[0407] The measured parameters were compared with the growth of a control mutant (100%) that did not contain the active compound and with blank values ​​that did not contain fungi, and the relative growth of the pathogen for each active compound was determined in percentage units.

[0408] greenhouse The compound was dissolved in a mixture of acetone and / or dimethyl sulfoxide and Wetol, a wetting agent / emulsifier based on ethoxylated alkylphenol, in a solvent-emulsifier ratio of 99:1 (by volume), to a total volume of 5 ml. Then, water was added to make a total volume of 100 ml.

[0409] Next, this stock solution was diluted with the solvent-emulsifier-water mixture described, to the final concentrations shown in the table below.

[0410] Example 1 - Preventive fungicidal control of Botrytis cinerea in bell pepper leaves Pepper seedlings were grown in pots until they had 4-5 leaves. These plants were sprayed with the aforementioned spray solution containing concentrated active ingredients or mixtures listed in the table below until it ran down. The following day, the plants were inoculated with biomalt or DOB aqueous solution containing a suspension of Botrytis cinerea spores. The plants were then immediately moved to a humidified room. After 5 days at 22-24°C and saturated relative humidity, the degree of fungal damage to the leaves was visually evaluated as the percentage of diseased leaf area.

[0411] In this test, Examples Ex-1, Ex-2, Ex-3, Ex-5, Ex-6, Ex-7, Ex-8, Ex-9, Ex-11, Ex-12, Ex-16, Ex-19, Ex-20, Ex-24, Ex-25, Ex-31, Ex-33, Ex-39, Ex-40, Ex-41, Ex-45, Ex-46, Ex-49, Ex-50, Ex-51, Ex-52, Ex-53, Ex-56, Ex-60, Ex-6 Samples treated with 125 ppm of the active substance (Ex-63, Ex-64, Ex-67, Ex-68, Ex-69, Ex-70, Ex-72, Ex-73, Ex-80, Ex-81, Ex-82, Ex-83, Ex-85, Ex-86, Ex-87, Ex-89, Ex-91, Ex-92) each showed less than 26% pathogen growth compared to untreated samples which showed 90% pathogen growth.

[0412] Example 2 - Preventive fungicidal control of Botrytis cinerea in bell pepper leaves Pepper seedlings were grown in pots until they had 4-5 leaves. These plants were sprayed with the aforementioned spray solution containing concentrated active ingredients or mixtures listed in the table below until it ran down. After 7 days, the plants were inoculated with biomalt or DOB aqueous solution containing a suspension of Botrytis cinerea spores. The plants were then immediately moved to a humidified room. After 5 days at 22-24°C and saturated relative humidity, the degree of fungal damage to the leaves was visually evaluated as the percentage of diseased leaf area.

[0413] In this test, samples treated with 125 ppm of the active substance according to Examples Ex-1, Ex-7, Ex-11, Ex-16, Ex-19, Ex-20, Ex-25, Ex-31, Ex-33, Ex-39, and Ex-40 each showed less than 20% pathogen growth compared to untreated samples which showed 90% pathogen growth.

[0414] Example 3 - Preventive fungicidal control of soybean ring spot disease caused by Corynespora cassiicola Soybean seedlings were grown in pots. These plants were sprayed with the aforementioned spray solution containing concentrated active ingredients or mixtures listed in the table below until it ran down. The following day, the plants were inoculated with biomalt or DOB aqueous solution of Corynespora cassiicola. The test plants were then cultivated for 8 days in a greenhouse at 22°C and 90% relative humidity. The degree of leaf damage by the fungus was visually evaluated as the percentage of diseased leaf area.

[0415] In this test, samples treated with 125 ppm of the active substance according to Example Ex-1 showed less than 11% pathogen growth compared to untreated samples which showed 90% pathogen growth.

[0416] Example 4 - Preventive fungicidal control of white mold disease in soybeans caused by Sclerotinia sclerotiorum Soybean seedlings were grown in pots. These plants were sprayed with the aforementioned spray solution containing concentrated active ingredients or mixtures listed in the table below until it ran down. The following day, the treated plants were inoculated with a suspension containing mycelium of Sclerotinia sclerotiorum. The test plants were then cultivated for 6 days in a greenhouse at 23°C and 80-85% relative humidity. The degree of leaf damage by the fungus was visually evaluated as the percentage of diseased leaf area.

[0417] In this test, samples treated with 125 ppm of the active substance according to Examples Ex-1, Ex-2, Ex-3, Ex-16, Ex-19, Ex-20, Ex-25, Ex-40, Ex-41, Ex-45, Ex-46, Ex-49, Ex-51, Ex-53, Ex-61, Ex-64, Ex-67, Ex-68, Ex-72, Ex-73, Ex-81, Ex-86, Ex-87, Ex-89, and Ex-91 each showed less than 23% pathogen growth compared to untreated samples which showed 90% pathogen growth.

[0418] Example 5 - Preventive fungicidal control of white mold disease in cabbage caused by Sclerotinia sclerotiorum Cabbage plants were grown in pots until they had 13-14 leaves. These plants were then sprayed with the aforementioned spray solution containing concentrated active ingredients or mixtures thereof, as listed in the table below, until it ran down.

[0419] The plants were air-dried. The following day, 50 μL of a mixture of crushed petals, methylcellulose, water, and yeast-bacto-peptone medium (containing spores of Sclerotinia sclerotiorum) was inoculated onto cabbage leaves. After 8 days at 21°C and 60% relative humidity, the degree of fungal damage to the leaves was visually assessed as the percentage of diseased leaf area.

[0420] In this test, samples treated with 125 ppm of the active substance according to Examples Ex-20, Ex-25, Ex-46, Ex-49, Ex-56, Ex-68, Ex-72, Ex-80, Ex-81, Ex-82, Ex, and Ex-83 each showed less than 23% pathogen growth compared to untreated samples which showed 90% pathogen growth.

Claims

1. Equation I 【Chemistry 1】 (Y is N, CR) １ And; Z is S, SO, or SO ２ And, R １ In each case, H, halogen, CN, C １ ~C ４ Alkyl, C １ ~C ４ Selected independently from alkyl halogens; R ２ is, in each case, independently selected from halogen, CN, C １ to C ６ alkyl, C １ to C ６ haloalkyl, C ２ to C ６ alkenyl, C ２ to C ６ haloalkenyl, C ２ to C ６ alkynyl, C ２ to C ６ haloalkynyl, O-C １ to C ６ alkyl, O-C ２ to C ６ alkenyl, O-C ２ to C ６ alkynyl, C ３ to C ６ cycloalkyl, S-C １ to C ６ alkyl, S-C ２ to C ６ alkenyl, S-C ２ to C ６ alkynyl; R ３ In each case, halogen, CN, C １ ~C ６ Alkyl, C １ ~C ６ Halogenated alkyl, C ２ ~C ６ Alkenil, C ２ ~C ６ Halogenated alkenyl, C ２ ~C ６ Alkinyl, C ２ ~C ６ Halogynyl, O-C １ ~C ６ Alkyl, O-C ２ ~C ６ Alkenyl, O-C ２ ~C ６ Alkinyl, C ３ ~C ６ Cycloalkyl, S-C １ ~C ６ Alkyl, S-C ２ ~C ６ Alkenil, S-C ２ ~C ６ Selected independently of Alkinnil; R ４ In each case, H, halogen, CN, C １ ~C ４ Alkyl, C １ ~C ４ Selected independently from alkyl halogens; R ５ In each case, hydrogen, halogen, CN, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C ２ ~C ６ Alkenil, C ２ ~C ６ Haloalkenil, C ２ ~C ６ Alkinyl, C ２ ~C ６ Haloalkynyl, phenyl, benzyl, 5-membered or 6-membered heteroaryl, or 5-membered or 6-membered CH ２ - Selected independently from heteroaryls; the heteroaryl contains one, two, or three heteroatoms selected from N, O, and S; the aliphatic or aromatic group is unsubstituted or has one, two, or three substituents R ５ａ Having; Each R ５ａ These are halogen, CN, and C, independently. １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl or O-C １ ~C ６ It is alkyl; R ６ is, in each case, independently selected from hydrogen, halogen, CN, C １ to C ６ alkyl, C １ to C ６ haloalkyl, C ２ to C ６ alkenyl, C ２ to C ６ haloalkenyl, C ２ to C ６ alkynyl, C ２ to C ６ haloalkynyl, phenyl, benzyl, a 5- or 6-membered heteroaryl or a 5- or 6-membered CH ２ -heteroaryl; said heteroaryl contains 1, 2 or 3 heteroatoms selected from N, O and S; said aliphatic or aromatic group is unsubstituted or has 1, 2 or 3 substituents R ６ａ ; Each R ６ａ These are halogen, CN, and C, independently. １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl or O-C １ ~C ６ It is alkyl; Or, R ５ and R ６ They both form an oxo group (=O); or a thioxo group (=S); Or, R ５ and R ６ Together with the carbon atoms to which they are bonded, they form a 3-membered, 4-membered, 5-membered, or 6-membered saturated carbocyclic ring or a 3-membered, 4-membered, 5-membered, or 6-membered saturated heterocyclic ring containing 1, 2, or 3 heteroatoms selected from O and S as ring members; the carbocyclic ring or heterocyclic ring is unsubstituted or has 1, 2, or 3 substituents R ５６ Having; Each R ５６ These are halogens and C １ ~C ６ Alkyl or C １ ~C ６ It is a haloalkyl; R ７ In each case, hydrogen, halogen, CN, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C ２ ~C ６ Alkenil, C ２ ~C ６ Haloalkenil, C ２ ~C ６ Alkinyl, C ２ ~C ６ Haloalkynyl, phenyl, benzyl, 5-membered or 6-membered heteroaryl, or 5-membered or 6-membered CH ２ A heteroaryl group is independently selected from heteroaryl groups; the heteroaryl group contains one, two, or three heteroatoms selected from N, O, and S; and the aliphatic or aromatic group is unsubstituted or has one, two, or three substituents R ７ａ Having; Each R ７ａ These are halogen, CN, and C, independently. １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl or O-C １ ~C ６ It is alkyl; R ８ In each case, hydrogen, halogen, CN, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C ２ ~C ６ Alkenil, C ２ ~C ６ Haloalkenil, C ２ ~C ６ Alkinyl, C ２ ~C ６ Haloalkynyl, phenyl, benzyl, 5-membered or 6-membered heteroaryl, or 5-membered or 6-membered CH ２ A heteroaryl group is independently selected from heteroaryl groups; the heteroaryl group contains one, two, or three heteroatoms selected from N, O, and S; and the aliphatic or aromatic group is unsubstituted or has one, two, or three substituents R ８ａ Having; Each R ８ａ These are halogen, CN, and C, independently. １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl or O-C １ ~C ６ It is alkyl; Or, R ７ and R ８ Together with the carbon atoms to which they are bonded, they form a 3-membered, 4-membered, 5-membered, or 6-membered saturated carbon ring or a 3-membered, 4-membered, 5-membered, or 6-membered saturated heterocycle containing one, two, or three heteroatoms selected from O and S as ring members; In each case, X is halogen, CN, C １ ~C ６ Alkyl, C １ ~C ６ Haloalkyl, C ２ ~C ６ Alkenil, C ２ ~C ６ Alkinyl, C ３ ~C ６ Cycloalkyl, C １ ~C ６ Alkoxy or C １ ~C ６ Haloalkoxy, phenyl, benzyl, phenoxy, benzoxy, C １ ~C ６ Independently selected from thioalkyl groups; phenyl, benzyl, phenoxy, and benzoxy are either unsubstituted or halogenated, CN, and C. １ ~C ６ Alkyl or C １ ~C ６ It may also be substituted with a haloalkyl; n is 0, 1, 2, or 3; however, Y is CR １ If R ５ , R ６ , R ７ and R ８ (It is not possible for all of them to be H.) Compounds thereof, or their N-oxides, tautomers, stereoisomers, or agriculturally acceptable salts.

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

3. R ２ C １ ~C ６ A compound according to any one of claims 1 to 2, wherein it is alkyl.

4. R ２ ga CH ３ The compound according to any one of claims 1 to 3.

5. R ３ However, C １ ~C ６ Alkyl, C １ ~C ６ A compound according to any one of claims 1 to 4, selected from halogen alkyls.

6. R ３ However, CH ３ or CHF ２ The compound according to any one of claims 1 to 5.

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

8. R ５ and R ６ However, H or C １ ~C ６ A compound according to any one of claims 1 to 7, wherein it is alkyl.

9. R ５ and R ６ However, along with the C atom to which they are bonded, ３ ~C ６ A compound according to any one of claims 1 to 8, which forms a cycloalkyl or (=O) group.

10. R ７ and R ８ However, H or C １ ~C ６ A compound according to any one of claims 1 to 9, wherein it is alkyl.

11. X is halogen, C １ ~C ６ Alkyl, O-C １ ~C ６ Alkyl, O-C １ ~C ６ A compound according to any one of claims 1 to 10, selected from halogen alkyls.

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

13. A method for controlling plant pathogenic fungi, comprising treating the fungi, or a material, plant, soil, or seed to be protected from fungal invasion, with an effective amount of at least one compound of formula I described in any one of claims 1 to 11 or the composition described in claim 12.

14. Seeds coated with at least one compound of formula I according to any one of claims 1 to 11 or an agriculturally acceptable salt thereof, or the composition according to claim 12, in an amount of 0.1 to 10 kg per 100 kg of seeds.

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