Novel substituted pyridines as bactericides

Abstract

The present invention relates to a compound represented by formula (I) [Case 1] JPEG2024519815000064.jpg39170, where the variables are defined as set forth in the specification and claims. The present invention further relates to uses and compositions thereof.

Description

[Technical Field]

[0001] This invention relates to novel pyridine compounds as fungicides, as well as their N-oxides and salts, and their uses. The invention also relates to compositions comprising at least one compound I, methods for controlling plant pathogens, and seeds coated with at least one compound of formula I. [Background technology]

[0002] International Publication Nos. 201018686 and 201347441 disclose several pyridine compounds. However, in many cases, especially at low application rates, the bactericidal 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 pathogens. Another object of the present invention is to provide fungicides having improved toxicological properties or improved environmental fate properties. [Overview of the project] [Means for solving the problem]

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

[0004] Therefore, the present invention relates to a bactericide, Formula I [ka] (In the formula, R 1 H is; R 2in each case, independently, selected from halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, O-C1-C6-alkyl, C3-C6-cycloalkyl; R 3 in each case, independently, selected from C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-haloalkenyl, C2-C6-alkynyl, O-C1-C6-alkyl, C3-C6-cycloalkyl; R 4 is H; R 5 in each case, independently, selected from H, F, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, phenyl, benzyl, that moiety is unsubstituted or substituted by 1 to 3 groups R 5a and the 1 to 3 groups R 5a are independently selected from halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, O-C1-C6-alkyl; R 6 in each case, independently, selected from H, F, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, phenyl, benzyl, R 6 that moiety is unsubstituted or substituted by 1 to 3 groups R 6a and the 1 to 3 groups R 6a are independently selected from halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, O-C1-C6-alkyl; or R 5 and R 6 together with the C atom to which they are attached form =O; or R 5 and R 6These, together with the C atom to which they are bonded, 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; the cycloalkyl or heterocycle may be unsubstituted or substituted with halogens, C1-C6-alkyl, or C1-C6-halogenalkyl; R 7 In each case, independently selected from H, F, CN, C1-C6-alkyl, C1-C6-halogen alkyl, C2-C6-alkenyl, phenyl, and benzyl, That portion is either unsubstituted or contains 1 to 3 groups R 7a It is substituted by 1 to 3 groups R 7a These are independently selected from halogen, CN, C1-C6-alkyl, C1-C6-halogen alkyl, and O-C1-C6-alkyl; R 8 In each case, independently selected from H, F, CN, C1-C6-alkyl, C1-C6-halogen alkyl, C2-C6-alkenyl, phenyl, and benzyl, That portion is either unsubstituted or contains 1 to 3 groups R 8a It is substituted by 1 to 3 groups R 8a These are independently selected from halogen, CN, C1-C6-alkyl, C1-C6-halogen alkyl, and O-C1-C6-alkyl; or R 7 and R 8 These, together with the C atom to which they are bonded, 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; In each case, X is independently selected from halogen, CN, C1-C6-alkyl, C1-C6-halogen alkyl, O-C1-C6-alkyl, O-C1-C6-halogen alkyl, C3-C6-cycloalkyl, C2-C6-alkenyl, and C2-C6-alkynyl; n is 0, 1, 2, or 3, however, R 5 , R 6, R 7 , R 8 (Not all of them can be H) This relates to compounds, their N-oxides, and agriculturally acceptable salts.

[0005] N-oxides can be prepared from the compounds of the present invention according to conventional oxidation methods, for example, by treating compound I with an organic peracid such as metachloroperbenzoic acid (see International Publication No. 03 / 64572 or J.Med.Chem. 38(11), 1892-903, 1995); or with an inorganic oxidizing agent such as hydrogen peroxide (see J.Heterocyc.Chem. 18(7), 1305-8, 1981) or oxone (see J.Am.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 compound of formula I include, in particular, cationic salts or acid addition salts of acids in which the cation and anion do not adversely affect the bactericidal 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, which may optionally be substituted with 1 to 4 C1-C4 alkyl substituents and / or 1 phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, and further, 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 chloride, bromide, fluoride, bisulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and C1-C4 alkanic acid anions, preferably formate, acetate, propionate, and butyrate. 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 restricted rotations of single bonds of asymmetric groups, and geometric isomers. These also form part of the subject matter of the present invention. Those skilled in the art will understand that one stereoisomer may be more active and / or exhibit beneficial effects when concentrated relative to or separated from other stereoisomers. Furthermore, 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., racemates, individual stereoisomers, or optically active compounds.

[0009] The compound of formula I may exist in different crystalline forms that 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 of substituents, particularly those shown in the table below for each substituent shown herein in relation to Compound I, also apply to the intermediates accordingly. Thus, the substituents in each case have meanings as defined herein, either independently or more preferably in combination.

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

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

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

[0015] The term "C1-C6-alkyl" refers to a linear or branched saturated hydrocarbon group having 1 to 6 carbon atoms, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, hexyl, 1-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" means an alkyl group having one or six carbon atoms as defined above, in which some or all of the hydrogen atoms in these groups may be substituted by halogen atoms as described above. Examples include "C1-C2 halogen alkyl," 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-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, or pentafluoroethyl.

[0017] The term "C1-C6 alkoxy" refers to a linear or branched alkyl group having 1 to 6 carbon atoms bonded via oxygen at any position on the alkyl group. Examples include "C1-C4 alkoxy" groups, such as methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, or 1,1-dimethylethoxy.

[0018] The term "C1-C6 halogen alkoxy" refers to the C1-C6 alkoxy groups defined above, in which some or all of the hydrogen atoms in these groups may be substituted by halogen atoms as described above. Examples include "C1-C4 halogen alkoxy" groups, e.g., OCH2F, OCHF2, OCF3, OCH2Cl, OCHCl2, OCl3, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, OC2F5, 2-fluoropropoxy Examples include 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, OCH2-C2F5, OCF2-C2F5, 1-fluoromethyl-2-fluoroethoxy, 1-chloromethyl-2-chloroethoxy, 1-bromomethyl-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy, or nonafluorobutoxy.

[0019] 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.

[0020] The term "C2-C6 halogenalkenyl" means an alkyl group having two or six carbon atoms as defined above, in which some or all of the hydrogen atoms in these groups may be substituted by halogen atoms as described above.

[0021] The term "C2-C6-alkenyloxy" refers to a linear or branched alkenyl group having 2 to 6 carbon atoms bonded via oxygen at any position on the alkenyl group. An example is the "C2-C4-alkenyloxy" group.

[0022] 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 the "C2-C4-alkynyl" group, 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.

[0023] The term "C2-C6-halogenal alkynyl" means an alkyl group having two or six carbon atoms as defined above, in which some or all of the hydrogen atoms in these groups may be substituted by halogen atoms as described above.

[0024] The term "C2-C6-alkynyloxy" refers to a linear or branched alkynyl group having 2 to 6 carbon atoms bonded via oxygen at any position on the alkynyl group. An example is the "C2-C4-alkynyloxy" group.

[0025] 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-, 4-, 5-, 6-, 7-, 8-, 9- or 10-membered carbocyclyl or carbon rings are "C3-C6 10 - It is a cycloalkyl compound.

[0026] The term "C3-C6-cycloalkenyl" refers to monocyclic partially unsaturated 3-, 4-, 5-, or 6-membered carbon rings having 3 to 6 carbon ring members and at least one double bond, such as cyclopentenyl, cyclopentadienyl, and cyclohexadienyl. Therefore, partially unsaturated 3-, 4-, 5-, 6-, 7-, 8-, 9-, or 10-membered carbocyclyls or carbon rings are "C3-C 10 - It is a cycloalkenyl.

[0027] The term "C3-C8-cycloalkyl-C1-C4-alkyl" refers to an alkyl group having 1-4 carbon atoms (as defined above), in which one hydrogen atom of the alkyl group is substituted by a cycloalkyl group having 3-8 carbon atoms (as defined above).

[0028] 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 heteroring containing 1, 2, 3, or 4 heteroatoms selected from N, O, and S" is understood to mean both saturated and partially unsaturated heterorings, where the ring member atoms of the heteroring include carbon atoms, plus 1, 2, 3, or 4 heteroatoms independently selected from the group O, N, and S. For example, A three- or four-membered saturated heterocycle containing one or two heteroatoms selected from the group consisting of O, N, and S as ring members, such as oxirane, aziridine, thiirane, oxetane, azetidine, thietan, [1,2]dioxetane, [1,2]dithietan, [1,2]diazetidine; and 5- or 6-membered saturated or partially unsaturated heterocycles containing 1, 2, or 3 heteroatoms from the group consisting of O, N, and S as ring members, e.g., 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl Nyl, 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-dihydro Roflu-3-yl, 2,4-dihydroflu-2-yl, 2,4-dihydroflu-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-I Soxazolin-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-4-yl, 3,4-dihydro Rooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 2-piperidinyl, 3-piperidinyl, 4-piperidinyl, 1,3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, 1,3,5-hexahydrotriazine-2-yl and 1,2,4-hexahydrotriazine-3-yl and the corresponding -ylidene group; and, Seven-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 Zepine-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]oxe2,3,6,7-tetrahydro[1H]azepine-1-,-2-,-3-,-4-,-5-,-6- or-7-yl, hexahydroazepine-1-,-2-,-3- or-4-yl, tetra- and hexahydrooxepinyl 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- Ilyl, 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.

[0029] The term "substituted" means that a substituent is substituted by one, two, three, or up to the maximum possible number of substituents.

[0030] 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, such as 5-membered heteroaryls, such as pyrrole-1-yl, pyrrole-2-yl, pyrrole-3-yl, thien-2-yl, thien-3-yl, furan-2-yl, furan-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, thiazole-2 -yl, thiazole-4-yl, thiazole-5-yl, isothiazole-3-yl, isothiazole-4-yl, isothiazole-5-yl, 1,2,4-triazolyl-1-yl, 1,2,4-triazol-3-yl, 1,2,4-triazol-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 6-membered heteroaryl, e.g., 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.

[0031] Specific embodiments of the compounds of the present invention are described below. There, the specific meaning of each substituent is further detailed, and its meaning is that in each case it is itself, but any combination of them also constitutes a specific embodiment of the present invention.

[0032] Furthermore, with respect to the variables, the embodiment of compound I generally applies to the intermediate as well.

[0033] According to one embodiment of the compound of formula I, R 1 H is H.

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

[0035] 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.

[0036] According to yet another embodiment of formula I, R 2 It is F.

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

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

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

[0040] According to yet another embodiment of formula I, R 2 These are C1-C6 alkyl groups, particularly C1-C4 alkyl groups, such as CH3 or C2H5, particularly CH3 or CH2CH3.

[0041] According to yet another embodiment of formula I, R 2 These are C1-C6 halogen alkyl groups, particularly C1-C4 halogen alkyl groups, such as CF3.

[0042] According to yet another 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.

[0043] According to a further specific embodiment of formula I, R 2 These are O-C1~C6-alkyl groups, particularly C1~C4-alkyl groups, and more specifically C1~C2-alkoxy groups. 2 These are OCH3 or OCH2CH3, etc.

[0044] According to yet another embodiment of formula I, R 2 These are C3-C6 cycloalkyl groups, particularly cyclopropyl or cyclobutyl groups.

[0045] R according to the present invention 2 Particularly preferred embodiments are shown in Table P2 below, where each row from P2-1 to P2-19 corresponds to one specific embodiment of the present invention, and P2-1 to P2-19 are also preferred embodiments of the present invention in any combination with each other. 2 The connection point to the carbon atom to which it is bonded is indicated by "#" in the diagram.

[0046] [Table 1]

[0047] According to one embodiment of formula I, R 3 The group is selected from C1-C6 alkyl, C1-C6 halogen alkyl, particularly CH3, C2H5, CF3, CH2F, CHF2, more specifically CH3, CH2F, CF2H, CF3, cyclopropyl, cyclobutyl, most preferably CH3, CF3, CF2H.

[0048] According to yet another embodiment of formula I, R 3 These are C1-C6 alkyl groups, particularly C1-C4 alkyl groups, such as CH3 or C2H5, particularly CH3 or CH2CH3.

[0049] According to yet another embodiment of formula I, R 3 These are C1-C6 halogen alkyl groups, particularly C1-C4 halogen alkyl groups, such as CF3, FCH2, F2CH, and CF3CH2.

[0050] 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.

[0051] According to a further specific embodiment of formula I, R 3 These are O-C1~C6-alkyl groups, particularly C1~C4-alkyl groups, and more specifically C1~C2-alkoxy groups. 3 These are OCH3 or OCH2CH3, etc.

[0052] According to yet another embodiment of formula I, R 3 These are C3-C6 cycloalkyl groups, particularly cyclopropyl and cyclobutyl groups.

[0053] R according to the present invention 3 Particularly preferred embodiments are shown in Table P3 below, where each row from P3-1 to P3-15 corresponds to one specific embodiment of the present invention, and P3-1 to P3-15 are also preferred embodiments of the present invention in any combination with each other. 3 The connection point to the carbon atom to which it is bonded is indicated by "#" in the diagram.

[0054] [Table 2]

[0055] According to one embodiment of the compound of formula I, R 4 H is H.

[0056] According to one embodiment of the compound of formula I, R 5 In each case, the elements are independently selected from H, F, CN, C1-C6-alkyl, C1-C6-halogen alkyl, C2-C6-alkenyl, phenyl, and benzyl, and they are either unsubstituted or have 1-3 R groups. 5a It is substituted by 1 to 3 groups R 5aThese elements are independently selected from halogen, CN, C1-C6-alkyl, C1-C6-halogen alkyl, and O-C1-C6-alkyl.

[0057] 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), H (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.

[0058] According to one further embodiment of the compound of formula I, R 5 It is either CH3 or CF3.

[0059] According to a further embodiment of the compound of formula I, R 5 This is CH3.

[0060] According to a further embodiment of the compound of formula I, R 5 H is H.

[0061] According to a further embodiment of the compound of formula I, R 5 These are H, CH2CH3, CH(CH3)2, CH(CH3)CH2CH3, C(CH3)3, CH2-CH(CH3)2, and CH2-C(CH3)3.

[0062] 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.

[0063] According to one embodiment of the compound of formula I, R 6In each case, the following are independently selected from H, F, CN, C1-C6-alkyl, C1-C6-halogen alkyl, C2-C6-alkenyl, phenyl, and benzyl. That portion is either unsubstituted or contains 1 to 3 groups R 6a It is substituted by 1 to 3 groups R 6a These elements are independently selected from halogen, CN, C1-C6-alkyl, C1-C6-halogen alkyl, and O-C1-C6-alkyl.

[0064] According to one embodiment of the compound of formula I, R 6 In each case, the element is independently selected from C1-C6 alkyl (Embodiment 6.1) and H (Embodiment 6.2).

[0065] According to a further embodiment of the compound of formula I, R 6 are H, CH3, CH2CH3, CH(CH3)2, CH(CH3)CH2CH3, C(CH3)3, CH2-CH(CH3)2, CH2-C(CH3)3, CH2-CH(CH3)-C(CH3)3, CH2-CH2-C(CH3)3.

[0066] According to a further embodiment of the compound of formula I, R 5 and R 6 These, together with the C atom to which they are bonded, form a 3- to 6-membered saturated heterocycle containing 1, 2, or 3 heteroatoms from the group consisting of =O, C3-C6-cycloalkyl, or O and S; the cycloalkyl or heterocycle may be unsubstituted or substituted with halogens, C1-C6-alkyl, or C1-C6-halogenalkyl.

[0067] According to a further embodiment of the compound of formula I, R 5 and R 6 This forms =O (Embodiment 6.3).

[0068] According to a further embodiment of the compound of formula I, R 5 and R 6This forms a C3-C6 cycloalkyl group (Embodiment 6.4).

[0069] 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.

[0070] According to a further embodiment of the compound of formula I, R 5 and R 6 This forms a 3- to 6-membered saturated heterocycle containing one oxygen atom (Embodiment 6.5).

[0071] 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 are also preferred embodiments of the present invention in any combination with each other. 5 and R 6 The connection point to the carbon atom to which it is bonded is indicated by "#" in the diagram.

[0072] [Table 3]

[0073] [Table 4]

[0074] [Table 5]

[0075] According to one embodiment of the compound of formula I, R 7in each case, independently selected from H, F, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C1-C6-alkyl-O-C1-C6-alkyl, phenyl, benzyl, that moiety is unsubstituted or substituted by 1 to 3 groups R 7a and the 1 to 3 groups R 7a are, independently of one another, selected from halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, O-C1-C6-alkyl.

[0076] According to one embodiment of the compound of formula I, R 7 in each case, independently, is selected from C1-C6-alkyl (embodiment 7.1), C1-C6-haloalkyl (embodiment 7.2), C1-C6-alkyl-O-C1-C6-alkyl (embodiment 7.3), phenyl, CH2-phenyl (embodiment 7.4), where phenyl and CH2-phenyl are unsubstituted or substituted by 1 or 2 halogen atoms.

[0077] According to a further embodiment of the compound of formula I, R 7 is CH3 or CF3.

[0078] According to a further embodiment of the compound of formula I, R 7 is CH3.

[0079] According to a further embodiment of the compound of formula I, R 7 is H.

[0080] According to a further embodiment of the compound of formula I, R 7 is CH2CH3, CH(CH3)2, CH(CH3)CH2CH3, C(CH3)3, CH2-CH(CH3)2, CH2-C(CH3)3, CH2-O-CH3.

[0081] According to a further embodiment of the compound of formula I, R 7is phenyl, 2-F-phenyl, 4-F-phenyl, 2,4-F2-phenyl, 2-Cl-phenyl, 4-Cl-phenyl, CH2-phenyl, CH2-2-F-phenyl, CH2-4-F-phenyl.

[0082] In one embodiment of the compound of formula I, R 8 in each case is independently selected from H, F, CN, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C1-C6-alkyl-O-C1-C6-alkyl, phenyl, benzyl, C1-C6-alkyl-O-phenyl, and that moiety is unsubstituted or substituted by 1 to 3 groups R 6a and the 1 to 3 groups R 6a are independently of one another selected from halogen, CN, C1-C6-alkyl, C1-C6-haloalkyl, O-C1-C6-alkyl.

[0083] According to one embodiment of the compound of formula I, R 8 in each case is independently selected from C1-C6-alkyl (embodiment 8.1), C1-C6-alkyl-O-phenyl (embodiment 8.2), C1-C6-alkyl-O-C1-C6-alkyl (embodiment 8.3).

[0084] In a further embodiment of the compound of formula I, R 8 is CH2CH3, CH(CH3)2, CH(CH3)CH2CH3, C(CH3)3, CH2-CH(CH3)2, CH2-C(CH3)3, CH2-CH(CH3)-C(CH3)3, CH2-CH2-C(CH3)3, CH2-O-CH3, CH2-O-(CH3)3, CH2-O-phenyl.

[0085] According to a further embodiment of the compound of formula I, R 7 and R 8 together with the C atom to which they are attached form a 3- to 6-membered saturated heterocycle containing 1, 2 or 3 heteroatoms from the group consisting of C3-C6-cycloalkyl or O and S.

[0086] 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).

[0087] 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.

[0088] According to a further embodiment of the compound of formula I, R 7 and R 8 This forms a 3- to 6-membered saturated heterocycle containing one oxygen atom (Embodiment 8.5).

[0089] R according to the present invention 7 and R 8 Preferred embodiments are shown in Table P5 below, where rows P5-1 to P5-18 correspond to a specific embodiment of the present invention, and P5-1 to P5-18 are also preferred embodiments of the present invention in any combination with each other. 5 and R 6 The connection point to the carbon atom to which it is bonded is indicated by "#" in the diagram.

[0090] [Table 6]

[0091] [Table 7]

[0092] [Table 8]

[0093] 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).

[0094] According to one embodiment of the compound of formula I, X is independently selected from halogens and O-C1~C6-alkyls in each case.

[0095] According to one embodiment of the compound of formula I, X is independently selected from F or Cl in each case.

[0096] In one embodiment, Xn is as follows: [ka] As defined, and X is selected from F, Cl, I, CH3, cyclopropyl, CH=CH2, C≡CH, OCH3, OCHF2, CF3, CHF2, CH2CH3, CN.

[0097] In one embodiment, Xn is as follows: [ka] As defined, and X is selected from F, Cl, I, CH3, cyclopropyl, CH=CH2, C≡CH, OCH3, OCHF2, CF3, CHF2, CH2CH3, CN.

[0098] In one embodiment, Xn is as follows: [ka] As defined, and X is selected from F, Cl, I, CH3, cyclopropyl, CH=CH2, C≡CH, OCH3, OCHF2, CF3, CHF2, CH2CH3, CN.

[0099] In one embodiment, Xn is as follows: [ka] As defined, and X is selected from F, Cl, I, CH3, cyclopropyl, CH=CH2, C≡CH, OCH3, OCHF2, CF3, CHF2, CH2CH3, CN.

[0100] In one embodiment, Xn is as follows: [ka] As defined, and X is selected from F, Cl, I, CH3, cyclopropyl, CH=CH2, C≡CH, OCH3, OCHF2, CF3, CHF2, CH2CH3, CN.

[0101] In one embodiment, Xn is as follows: [ka] As defined, and X is selected from F, Cl, I, CH3, cyclopropyl, CH=CH2, C≡CH, OCH3, OCHF2, CF3, CHF2, CH2CH3, CN.

[0102] In one embodiment, Xn is as follows: [ka] As defined in , and X is F.

[0103] In one embodiment, Xn is as follows: [ka] As defined, and X is selected from F, Cl, I, CH3, cyclopropyl, CH=CH2, C≡CH, OCH3, OCHF2, CF3, CHF2, CH2CH3, CN.

[0104] In one embodiment, Xn is as follows: [ka] As defined in , and X is F.

[0105] In one embodiment, Xn is as follows: [ka] As defined in , and X is H.

[0106] In one embodiment, Xn is as follows: [ka] As defined, and X is selected from F, Cl, I, CH3, cyclopropyl, CH=CH2, C≡CH, OCH3, OCHF2, CF3, CHF2, CH2CH3, CN.

[0107] In one embodiment of the compound of formula I, n is 0.

[0108] In one embodiment of the compound of formula I, n is 1.

[0109] In one embodiment of the compound of formula I, n is 2.

[0110] Compounds of formula I contain one or more chiral centers and are generally obtained in racemic form. The R- and S-enantiomers can be separated and isolated in their pure form by methods known to those skilled in the art, such as using chiral HPLC.

[0111] Therefore, according to the present invention, the compound of formula I can be used in the following forms. - A racemic mixture of (R)-enantiomer and (S)-enantiomer; - A mixture of (R)-enantiomers and (S)-enantiomers in other proportions; - Pure (R)-enantiomer, or - A pure (S)-enantiomer.

[0112] According to certain embodiments of the present invention, the compound of formula I exists as a racemic composition of (R)-enantiomer and (S)-enantiomer, but the (R)-enantiomer and (S)-enantiomer may also exist in any other proportion, for example, as a pure enantiomer (R) or a pure enantiomer (S) of the compound of formula I.

[0113] According to one particular 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%.

[0114] According to further specific embodiments, 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%.

[0115] In a further embodiment, the present invention relates to a compound of formula I as defined below, wherein the variable R 2 , R 3 And relating to embodiments E.1 to E.275 listed in Table E, which represent preferred combinations of the embodiments defined above for each of X (represented by embodiments X.1 to X.6) and n. [ka]

[0116] [Table 9]

[0117] [Table 10]

[0118] [Table 11]

[0119] [Table 12]

[0120] [Table 13]

[0121] [Table 14]

[0122] [Table 15]

[0123] In a further embodiment, the present invention is R 5 This is represented by Embodiment 5.1, and R 6 This relates to Embodiments E.1 to E.275 listed in Table E, which are represented by Embodiment 6.1.

[0124] In a further embodiment, the present invention is R 5 This is represented by Embodiment 5.2, and R 6 This relates to Embodiments E.1 to E.275 listed in Table E, which are represented by Embodiment 6.1.

[0125] In a further embodiment, the present invention is R 5 This is represented by Embodiment 5.3, and R 6This relates to Embodiments E.1 to E.275 listed in Table E, which are represented by Embodiment 6.1.

[0126] In a further embodiment, the present invention is R 5 This is represented by Embodiment 5.4, and R 6 This relates to Embodiments E.1 to E.275 listed in Table E, which are represented by Embodiment 6.1.

[0127] In a further embodiment, the present invention is R 5 This is represented by Embodiment 5.1, and R 6 This relates to Embodiments E.1 to E.275 listed in Table E, which are represented by Embodiment 6.2.

[0128] In a further embodiment, the present invention is R 5 This is represented by Embodiment 5.2, and R 6 This relates to Embodiments E.1 to E.275 listed in Table E, which are represented by Embodiment 6.2.

[0129] In a further embodiment, the present invention is R 5 This is represented by Embodiment 5.3, and R 6 This relates to Embodiments E.1 to E.275 listed in Table E, which are represented by Embodiment 6.2.

[0130] In a further embodiment, the present invention is R 5 This is represented by Embodiment 5.4, and R 6 This relates to Embodiments E.1 to E.275 listed in Table E, which are represented by Embodiment 6.2.

[0131] In a further embodiment, the present invention is R 5 This is represented by Embodiment 5.1, and R 6 This relates to Embodiments E.1 to E.275 listed in Table E, which are represented by Embodiment 6.3.

[0132] In a further embodiment, the present invention is R 5 This is represented by Embodiment 5.2, and R6 This relates to Embodiments E.1 to E.275 listed in Table E, which are represented by Embodiment 6.3.

[0133] In a further embodiment, the present invention is R 5 This is represented by Embodiment 5.3, and R 6 This relates to Embodiments E.1 to E.275 listed in Table E, which are represented by Embodiment 6.3.

[0134] In a further embodiment, the present invention is R 5 This is represented by Embodiment 5.4, and R 6 This relates to Embodiments E.1 to E.275 listed in Table E, which are represented by Embodiment 6.3.

[0135] 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 by Embodiment 6.4.

[0136] 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 by Embodiment 6.5.

[0137] In a further embodiment, the present invention is R 7 This is represented by Embodiment 7.1, and R 8 This relates to Embodiments E.1 to E.275 listed in Table E, which are represented by Embodiment 8.1.

[0138] In a further embodiment, the present invention is R 7 This is represented by Embodiment 7.2, and R 8 This relates to Embodiments E.1 to E.275 listed in Table E, which are represented by Embodiment 8.1.

[0139] In a further embodiment, the present invention is R 7 This is represented by Embodiment 7.3, and R 8relates to Embodiments E.1 to E.275 listed in Table E, represented by Embodiment 8.1.

[0140] In a further aspect, the present invention is R 7 is represented by Embodiment 7.4, and R 8 relates to Embodiments E.1 to E.275 listed in Table E, represented by Embodiment 8.1.

[0141] In a further aspect, the present invention is R 7 is represented by Embodiment 7.1, and R 8 relates to Embodiments E.1 to E.275 listed in Table E, represented by Embodiment 8.2.

[0142] In a further aspect, the present invention is R 7 is represented by Embodiment 7.2, and R 8 relates to Embodiments E.1 to E.277 listed in Table E, represented by Embodiment 8.2.

[0143] In a further aspect, the present invention is R 7 is represented by Embodiment 7.3, and R 8 relates to Embodiments E.1 to E.277 listed in Table E, represented by Embodiment 8.2.

[0144] In a further aspect, the present invention is R 7 is represented by Embodiment 7.4, and R 8 relates to Embodiments E.1 to E.277 listed in Table E, represented by Embodiment 8.2.

[0145] In a further aspect, the present invention is R 7 is represented by Embodiment 7.1, and R 8 relates to Embodiments E.1 to E.277 listed in Table E, represented by Embodiment 8.3.

[0146] In a further aspect, the present invention is R 7 is represented by Embodiment 7.2, and R8 This relates to Embodiments E.1 to E.277 listed in Table E, which are represented by Embodiment 8.3.

[0147] In a further embodiment, the present invention is R 7 This is represented by Embodiment 7.3, and R 8 This relates to Embodiments E.1 to E.277 listed in Table E, which are represented by Embodiment 8.3.

[0148] In a further embodiment, the present invention is R 7 This is represented by Embodiment 7.4, and R 8 This relates to Embodiments E.1 to E.277 listed in Table E, which are represented by Embodiment 8.3.

[0149] In a further embodiment, the present invention is R 7 and R 8 This relates to Embodiments E.1 to E.277 listed in Table E, which are represented by Embodiment 8.4.

[0150] In a further embodiment, the present invention is R 7 and R 8 This relates to Embodiments E.1 to E.277 listed in Table E, which are represented by Embodiment 8.7.

[0151] Preferred embodiments of the present invention are the following compounds IA-1, IA-2, IA-3, and IA-4. In these formulas, substituent R 5 , R 6 , R 7 and R 8 Furthermore, Xn is independently as defined above, or preferably as defined herein. [ka]

[0152] In particular, from the viewpoint of their use, according to one embodiment, compounds IA-1, IA-2, IA-3, and IA-4, summarized in Tables 1a to 7a, are preferred. Each of the groups described with respect to substituents in the table is further, independently of the combinations described, a particularly preferred embodiment of the substituent in question.

[0153] Table 1a Xn is H, and the R of each individual compound 5 and R 6 The meaning of each combination is that, in each case, the compounds of formulas IA-1, IA-2, IA-3, and IA-4 correspond to a row in Table B (compounds IA-1.1aB-1 to IA-1.1aB-25, IA-2.1aB-1 to IA-2.1aB-25, IA-3.1aB-1 to IA-3.1aB-25, and IA-4.1aB-1 to IA-4.1aB-25).

[0154] Table 2a Xn is 8-F, and the R of each individual compound 5 and R 6 The meaning of each combination is that, in each case, the compounds of formulas IA-1, IA-2, IA-3, and IA-4 (compounds IA-1.2aB-1 to IA-1.2aB-25, IA-2.2aB-1 to IA-2.2aB-25, IA-3.2aB-1 to IA-3.2aB-25, and IA-4.2aB-1 to IA-4.2aB-25) correspond to a row in Table B.

[0155] Table 3a Xn is 8-Cl, and the R of each individual compound 5 and R 6 The meaning of each combination is that, in each case, the compounds of formulas IA-1, IA-2, IA-3, and IA-4 correspond to a row in Table B (compounds IA-1.3aB-1 to IA-1.3aB-25, IA-2.3aB-1 to IA-2.3aB-25, IA-3.3aB-1 to IA-3.3aB-25, and IA-4.3aB-1 to IA-4.3aB-25).

[0156] Table 4a Xn is 7,8-F2, and the R of each individual compound 5 and R 6 The meaning of each combination is that, in each case, the compounds of formulas IA-1, IA-2, IA-3, and IA-4 correspond to a row in Table B (compounds IA-1.4aB-1 to IA-1.4aB-25, IA-2.4aB-1 to IA-2.4aB-25, IA-3.4aB-1 to IA-3.4aB-25, and IA-4.4aB-1 to IA-4.4aB-25).

[0157] Table 5a Xn is 5,8-F2, and the R of each individual compound 5 and R 6 The meaning of each combination is that, in each case, the compounds of formulas IA-1, IA-2, IA-3, and IA-4 (compounds IA-1.5aB-1 to IA-1.5aB-25, IA-2.5aB-1 to IA-2.5aB-25, IA-3.5aB-1 to IA-3.5aB-25, and IA-4.5aB-1 to IA-4.5aB-25) correspond to a row in Table B.

[0158] Table 6a Xn is 7-OCH3, and the R of each individual compound 5 and R 6 The meaning of each combination is that, in each case, the compounds of formulas IA-1, IA-2, IA-3, and IA-4 correspond to a row in Table B (compounds IA-1.6aB-1 to IA-1.6aB-25, IA-2.6aB-1 to IA-2.6aB-25, IA-3.6aB-1 to IA-3.6aB-25, and IA-4.6aB-1 to IA-4.6aB-25).

[0159] Table 7a Xn is 6,8-F2, and the R of each individual compound 5 and R 6The meaning regarding the combination of, in each case, corresponds to a row in Table B, the compounds of Formula I.A-1, I.A-2, I.A-3, I.A-4 (Compounds I.A-1.7a.B-1 to I.A-1.7a.B-25, I.A-2.7a.B-1 to I.A-2.7a.B-25, I.A-3.7a.B-1 to I.A-3.7a.B-25, I.A-4.7a.B-1 to I.A-4.7a.B-25).

[0160] Preferred embodiments of the present invention are the following Compounds I.B-1, I.B-2, I.B-3, I.B-4. In these formulas, the substituents R 5 , R 6 , R 7 and R 8 as well as Xn are, independently, as defined above or preferably as defined herein.

Chemical formula

[0161] Particularly from the perspective of their use, according to one embodiment, the compounds of Compounds I.B-1, I.B-2, I.B-3, I.B-4 summarized in Tables 1b to 7b are preferred. Each of the groups described regarding the substituents in the table is, furthermore, in itself, independent of the combination in which it is described, a particularly preferred embodiment of the substituent in question.

[0162] Table 1b When Xn is H, the meaning regarding the combination of R 5 and R 6 of each individual compound corresponds to a row in Table B, the compounds of Formula I.B-1, I.B-2, I.B-3, I.B-4 (Compounds I.B-1.1b.B-1 to I.B-1.1b.B-25, I.B-2.1b.B-1 to I.B-2.1b.B-25, I.B-3.1b.B-1 to I.B-3.1b.B-25, I.B-4.1b.B-1 to I.B-4.1b.B-25).

[0163] Table 2b When Xn is 8-F, R 5 and R6 The meaning of each combination is that, in each case, the compounds of formulas IB-1, IB-2, IB-3, and IB-4 correspond to a row in Table B (compounds IB-1.2bB-1 to IB-1.2bB-25, IB-2.2bB-1 to IB-2.2bB-25, IB-3.2bB-1 to IB-3.2bB-25, and IB-4.2bB-1 to IB-4.2bB-25).

[0164] Table 3b Xn is 8-Cl, and the R of each individual compound 5 and R 6 The meaning of each combination is that, in each case, the compounds of formulas IB-1, IB-2, IB-3, and IB-4 correspond to the row in Table B (compounds IB-1.3bB-1 to IB-1.3bB-25, IB-2.3bB-1 to IB-2.3bB-25, IB-3.3bB-1 to IB-3.3bB-25, and IB-4.3bB-1 to IB-4.3bB-25).

[0165] Table 4b Xn is 7,8-F2, and the R of each individual compound 5 and R 6 The meaning of each combination is that, in each case, the compounds of formulas IB-1, IB-2, IB-3, and IB-4 correspond to a row in Table B (compounds IB-1.4bB-1 to IB-1.4bB-25, IB-2.4bB-1 to IB-2.4bB-25, IB-3.4bB-1 to IB-3.4bB-25, and IB-4.4bB-1 to IB-4.4bB-25).

[0166] Table 5b Xn is 5,8-F2, and the R of each individual compound 5 and R 6The meaning of each combination is that, in each case, the compounds of formulas IB-1, IB-2, IB-3, and IB-4 correspond to a row in Table B (compounds IB-1.5bB-1 to IB-1.5bB-25, IB-2.5bB-1 to IB-2.5bB-25, IB-3.5bB-1 to IB-3.5bB-25, and IB-4.5bB-1 to IB-4.5bB-25).

[0167] Table 6b Xn is 7-OCH3, and the R of each individual compound 5 and R 6 The meaning of each combination is that, in each case, the compounds of formulas IB-1, IB-2, IB-3, and IB-4 correspond to a row in Table B (compounds IB-1.6bB-1 to IB-1.6bB-25, IB-2.6bB-1 to IB-2.6bB-25, IB-3.6bB-1 to IB-3.6bB-25, and IB-4.6bB-1 to IB-4.6bB-25).

[0168] Table 7b Xn is 6,8-F2, and the R of each individual compound 5 and R 6 The meaning of each combination is that, in each case, the compounds of formulas IB-1, IB-2, IB-3, and IB-4 correspond to a row in Table B (compounds IB-1.7bB-1 to IB-1.7bB-25, IB-2.7bB-1 to IB-2.7bB-25, IB-3.7bB-1 to IB-3.7bB-25, and IB-4.7bB-1 to IB-4.7bB-25).

[0169] [Table 16]

[0170] [Table 17]

[0171] The compounds of the present invention can be prepared as shown in the following scheme, 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. This synthesis utilizes starting materials that can be prepared starting from commercially available starting materials or compounds readily available according to conventional procedures.

[0172] For example, compound I can be prepared by a palladium-catalyzed Suzuki coupling reaction between a boronic acid derivative represented by formula (2) and a halogenated imidoyl derivative represented by formula (6) in an organic solvent using a palladium complex. As described in International Publication No. 2009119089A1, it is preferable to carry out the reaction at a high temperature, preferably 60 to 160°C, using 1 to 3 equivalents of the boronic acid derivative represented by formula 3 per imidoyl halide derivative (6). [ka]

[0173] The imidoyl compounds represented by formula (6) can be prepared by reacting a cyclic amide represented by formula (7) in the presence of triphenylphosphine and a suitable halogenating agent such as carbon tetrahalide, triphenylphosphine dichloride, phosgene, oxalyl chloride, or thionyl chloride, as described in U.S. Patent Application Publication No. 2011 / 0136782A1. [ka]

[0174] The compound represented by formula (7) can be prepared by converting the cyclic acetophenone derivative represented by formula (9) to an oxime via the Schmidt reaction, followed by a Beckmann rearrangement. Various variations of both reactions have been reported. The Schmidt reaction can be carried out, for example, by reacting a ketone with sodium azide and a strong acid such as concentrated hydrochloric acid, sulfuric acid, trifluoroacetic acid, or methanesulfonic acid, either without a solvent or in a solvent such as acetonitrile, chloroform, or methylene chloride. In the Beckmann rearrangement, the oxime of the carbonyl compound is reacted with polyphosphate or its trimethylsilyl ester, or at high temperature with a Lewis acid, such as aluminum triiodide or iron(III) chloride-impregnated montmorillonite or thionyl chloride, either without a solvent or in the presence of a solvent such as acetonitrile. Furthermore, as described in Heterocycles (1994), 38(2), 305-18; U.S. Patent Application Publication No. 2011 / 0136782A1, the oxime can also be prepared by forming a mesylate or tosylate and then treating it with a base such as an aqueous sodium hydroxide solution, or with a Lewis acid such as diethylaluminum chloride. [ka]

[0175] Alternatively, the compound represented by formula (7) can be prepared in a one-pot reaction by a copper(II)-catalyzed Beckmann rearrangement of ketone (9) under mild reaction conditions, using hydroxylamine-O-sulfonic acid as the aminer, as described in Synthesis 2019, 51(19), 3709-3714.

[0176] Oximes (8) can be prepared using known methods, as described in Bioorganic & Medicinal Chemistry (2008), 16(11), 6124-6130; Heterocyclic Communications (1998), 4(6), 547-557, by reacting hydroxylamine hydrochloride in a solvent such as ethanol, and then, if necessary, adding a base, such as pyridine, sodium acetate, or an aqueous sodium hydroxide solution, at a temperature up to the boiling point of the solvent. [ka]

[0177] The cyclic acetophenone derivatives represented by formula (9) are commercially available or can be obtained by starting from 2-hydroxyacetophenone via a classical cyclization reaction using the corresponding ketone in the presence of pyrrolidine, as described in Bioorganic & Medicinal Chemistry (2008), 16(11), 6124-6130; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1995).

[0178] The pending present invention is of formula Y: [ka] (In the formula, R 5 , R 6 , R 7 , R 8 (and Xn are as defined above.) The present invention further relates to the process of preparing the compound of formula I, including the reaction of the compound.

[0179] The pending present invention is based on formula Y [ka] (In the formula, R 5It is selected from the group consisting of H and C1-C6 alkyl groups. R 6 is selected from the group consisting of H, C1-C6-alkyl, or R 5 and R 6 These, together with the C atom to which they are bonded, form C3-C6 cycloalkyl groups; R 7 It is selected from the group consisting of H and C1-C6 alkyl groups. R 8 is selected from the group consisting of H, C1-C6-alkyl, or R 7 and R 8 These, together with the C atom to which they are bonded, form C3-C6 cycloalkyl groups; X is a halogen, C1-C6 alkyl; n is 0, 1, or 2. Further information on the compounds.

[0180] In one embodiment, R 5 It is selected from the group consisting of H and CH3, R 6 It is selected from the group consisting of H and CH3, or R 5 and R 6 These, together with the C atom to which they are bonded, form a cyclopropyl group; R 7 It is selected from the group consisting of H and CH3, R 8 It is selected from the group consisting of H and CH3, or R 7 and R 8 These, together with the C atom to which they are bonded, form a cyclopropyl group; X is Cl, F, or CH3. n is 0, 1, or 2.

[0181] In one further embodiment, the following compound Y is most preferred. [ka] [ka] [ka]

[0182] Compound I and its compositions are suitable as effective fungicides against a wide range of plant pathogens, including soil-borne fungi, particularly those belonging to the classes Plasmodiophoromycetes, Peronosporomycetes (synonymous with Oomycetes), Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, and Deuteromycetes (synonymous with Fungi imperfecti). These can be used for crop protection as foliar fungicides, seed coating fungicides, and soil fungicides.

[0183] Compound I and its compositions preferably include various cultivated plants, such as cereals, 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 (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, for example It is useful for controlling plant pathogens in oranges, lemons, grapefruits or tangerines; 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 plants; bananas; grapes (table grapes and grapes for grape juice); hops; turf; snowbell (also called 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.

[0184] More preferably, compound I and its compositions are used to control fungi on crops such as potatoes, sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rapeseed, legumes, sunflowers, coffee, or sugarcane; fruits; grapes; ornamental plants; or vegetables such as cucumbers, tomatoes, beans, or pumpkins.

[0185] The term “plant propagation material” is understood to refer to all reproductive parts of plants, such as seeds; as well as all viable plant materials that can be used for plant propagation, such as cuttings and tubers (e.g., potatoes). This 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.

[0186] Preferably, treatment of plant propagation material with compound I and its compositions is used to control fungi on cereals such as wheat, rye, barley, and oats; rice, maize, cotton, and soybeans.

[0187] According to the present invention, all of the above-mentioned cultivated plants are understood to include all species, subspecies, varieties, cultivars and / or hybrids belonging to each cultivated plant, and in particular include, but are not limited to, cereals such as wheat and barley, and winter and spring varieties of rapeseed, such as winter wheat, spring wheat, and winter barley.

[0188] 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), hatched maize or wild maize (Zea mays var. tunicata), and striped maize (Zea mays var. japonica).

[0189] Most soybean varieties are classified into indefinite and finite growth types, although the wild ancestor of soybeans, Glycine soja, is indefinite (PNAS 2010, 107(19)8563-856). Indefinite growth types (maturity groups, MG00~MG4.9) are characterized by continued plant growth even after flowering begins, while finite soybean varieties (MG5~MG8) are characterized by the fact that most of the plant growth is completed by the time flowering begins. According to the present invention, all soybean cultivars or varieties are included, and in particular, indefinite and finite cultivars or varieties are included.

[0190] The term "cultivated plant" is understood to include plants that have been 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 create mutations at specific loci in the plant genome. Many targeted mutagenesis techniques use 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 cannot be easily obtained 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. Such incorporated genes are also called transgenes, and plants containing such transgenes are called transgenic plants. In the process of plant transformation, several transformation events usually occur, each with a different genomic locus into which the transgene is incorporated. Plants containing a specific transgene at a particular genomic locus are typically described as containing a specific "event," which is referred to by the name of that event. Traits introduced or modified into plants include herbicide resistance, insect resistance, high yield, and tolerance to abiotic conditions such as drought.

[0191] Herbicide resistance is conferred through mutation and genetic engineering. Plants conferred resistance to acetolactate synthase (ALS) inhibitor herbicides through mutation breeding are, for example, plant varieties available under the name Clearfield®. Transgenes confer 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.

[0192] Transgenes that confer herbicide resistance traits include: glyphosate resistance conferring: cp4 epsps, epsps grg23ace5, mepsps, 2mepsps, gat4601, gat4621, goxv247; glufosinate resistance conferring: pat and bar; 2,4-D resistance conferring: aad-1, aad-12; dicamba resistance conferring: dmo; oxynyl herbicide resistance conferring: bxn; sulfonylurea herbicide resistance conferring: zm-hra, csr1-2, gm-hra, S4-HrA; ALS inhibitor resistance conferring: csr1-2; HPPD inhibitor resistance conferring: hppdPF, W336, avhppd-03.

[0193] 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 events 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 canola events that include 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.

[0194] The transgenes conferring insect resistance are preferably toxin genes and synthetic mutants thereof from Bacillus spp. 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 also be used. A further approach involves producing double-stranded RNA in plants using transgenes such as dvsnf7.

[0195] 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, 3253, 3257, 3258, 42317, BNLA-601, Event1, COT67B, COT102, T303-3, T304-40, GFM Cry1A, GK12, MLS9124, 281-24-236, 3006-210-23, GHB119, and SGK321.

[0196] Using the introduced gene athb17 (e.g., maize event MON87403) or bbx32 (e.g., soybean event MON87712), cultivated plants with increased yields are created.

[0197] Cultivated plants with modified oil content are created by 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).

[0198] By using cspB (corn event MON87460) and Hahb-4 (soybean event IND-φφ41φ-5), resistance to abiotic conditions such as drought can be created.

[0199] Trait combinations are often achieved by combining genes included in transformation events or by combining different events in the breeding process to obtain cultivated plants with accumulated traits. Preferred trait combinations 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 and resistance to one or more insects, combinations of herbicide resistance and yield increase, and combinations of herbicide resistance and resistance to abiotic conditions.

[0200] Plants containing single or cumulative 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 incorporated 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, concerning Canola Events MS1, MS8, RF3, GT73, MON88302, and KK179;Regarding Wata Events MON1445, MON15985, MON531 (MON15985), LLCotton25, MON88913, COT102, 281-24-236, 3006-210-23, COT67B, GHB614, T304-40, GHB119, MON88701, and 81910, see International Publication No. 02 / 034946, International Publication No. 02 / 100163, International Publication No. 02 / 100163, and International Publication No. 03 / 013224. International publication brochure No. 04 / 072235, International publication brochure No. 04 / 039986, International publication brochure No. 05 / 103266, International publication brochure No. 05 / 103266, International publication brochure No. 06 / 128573, International publication brochure No. 07 / 017186, International publication brochure No. 08 / 122406, International publication brochure No. 08 / 151780, International publication brochure No. 12 / 134808, International publication brochure No. 13 / 112527;Regarding 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, U.S. Patent Application No. 02 / 102582. U.S. Patent Application No. 03 / 126634, 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), U.S. Patent Application Publication No. 2007 / 292854, International Publication No. 07 / 142840 (brochure), International Publication Pamphlet No. 07 / 140256, International Publication Pamphlet No. 08 / 112019, International Publication Pamphlet No. 09 / 103049, International Publication Pamphlet No. 09 / 111263, International Publication Pamphlet No. 10 / 077816, International Publication Pamphlet No. 11 / 084621, International Publication Pamphlet No. 11 / 062904, International Publication Pamphlet No. 11 / 022469, International Publication Pamphlet No. 13 / 169923, International Publication Pamphlet No. 14 / 116854, International Publication Pamphlet No. 15 / 05 Pamphlet No. 3998, International Publication No. 15 / 142571; concerning Potato Events E12, F10, J3, J55, V11, X17, Y9, 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;Regarding 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, Regarding MON87701, MON87769, CV127, MON87705, DAS68416-4, MON87708, MON87712, SYHT0H2, DAS81419, DAS81419xDAS44406-6, and MON87751, see International Publication No. 04 / 074492, International Publication No. 06 / 130436, and International Publication No. 06 / 1 This can be found in brochures No. 08674, 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.

[0201] The use of compound I and its compositions in cultivated plants may produce plant-specific effects, including those involving specific transgenes or events. These effects may include changes in growth behavior or resistance to biological or abiotic stressors. These effects may include, in particular, increased yield, improved resistance or tolerance to insects, nematodes, fungi, bacteria, mycoplasmas, viruses, or viroid pathogens, as well as early growth, premature maturation or ripening, low or high temperature tolerance, and changes in the amino acid or fatty acid spectrum or content.

[0202] Compound I and its compositions are particularly suitable for controlling the following plant disease-causing substances: Albugo (white rust), which affects ornamental plants, vegetables (e.g., A. candida) and sunflowers (e.g., A. tragopogonis); Alternaria (black spot), which affects vegetables (e.g., A. dauci or A. porri), rapeseed (e.g., A. brassicicola or A. brassicae), sugar beets (A. tenuis), and fruits (e.g., A. grandis). ), those in rice, soybeans, potatoes and tomatoes (e.g., A. solani, A. grandis, or A. alternata), those in tomatoes (e.g., A. solani or A. alternata), and those in wheat (e.g., A. triticina); Aphanomyces species in sugar beets and vegetables; Ascochyta species in cereals and vegetables, e.g., A. tritici (anthracnose) in wheat and A. hordei in barley; Aureobasidium in maize. zeae) (synonymous with maize brown spot (Kapatiella zeae); Bipolaris and Drechslera species (Teleomorph: Cochliobolus species), for example, sesame leaf spot (D. maydis) or sooty spot (B. zeicola) in maize, for example, spot disease (B. sorokiniana) in cereals, for example, B. oryzae (B.oryzae; Blumeria (formerly Erysiphe) graminis (powdery mildew) in cereals (e.g., wheat or barley); gray mold (Botrytis cinerea) (teleomorph: Botryotinia fuckeliana: gray mold) in fruits and berries (e.g., strawberries), 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), grapes, forest plants and wheat; Bremia lactucae in lettuce lactucae) (downy mildew); Ceratocystis (synonymous with Ophiostoma) species (root rot or damping-off disease) in deciduous and evergreen trees, for example C. ulmi (Ulmus ulmi) in elm; Cercospora species (Cercospora spot disease), and maize (for example, gray spot: C. zeae-maydis), rice, sugar beet (for example, C. Those found in beticola, sugarcane, vegetables, coffee, soybeans (e.g., C. sojina or C. kikuchii), and rice; Cladobotryum species (synonymous with Dactylium) in mushrooms (e.g., C. mycophilum) (formerly Dactylium dendroides) dendroides, teleomorph: Nectria albertinii, Nectria rosella (synonymous with Hypomyces rosellus); Cladosporium species, such as those in tomatoes (e.g., C. fulvum: leaf mold) and those in grains, such as C. herbarum in wheat (C.herbarum) (black spot disease); Claviceps purpurea (corn rot) in cereals; Cochliobolus (anamorph: Helminthosporium of Bipolaris) species (spot disease), including those in maize (C. carbonum), cereals (e.g., C. sativus, anamorph: B. sorokiniana) and rice ( For example, C. miyabeanus (anamorph: H. oryzae); Colletotrichum (teleomorph: Glomerella) species (anthracnose), which are found in cotton (e.g., C. gossypii), in maize (e.g., C. graminicola: anthracnose root rot), soft fruit, and potatoes. Plants that are affected (e.g., C. coccodes: black spot disease), legumes (e.g., C. lindemuthianum), soybeans (e.g., C. truncatum or C. gleosporioides), vegetables (e.g., C. lagenarium or C. capsici), fruits (e.g., C. actatus) C. acutatum), C. coffee (e.g., C. coffeeum or C. kahawae), and C. gleosporioides in various crops; Corticium species in rice, e.g., C. sasakii (sheath blight); Corynespora cassiicola (leaf spot) in soybeans, cotton, and ornamental plants; Cycloconium species, e.g., C. oleaginum (C.oleaginum); Cylindrocarpon (e.g., fruit tree ulcer disease or weakness of young grapes, teleomorph: Nectria or Neonectria) in fruit trees, in grapes (e.g., C. liriodendri, teleomorph: Neonectria liriodendri) (Liriodendri), black foot disease, and those in ornamental plants; Dematophora (teleomorph: Roselinia) and Necatrix (root and stem rot) in soybeans; Diaporthe species in soybeans, e.g., D. phaseolorum (seedling blight); Dreshlera (synonymous with Helminthosporium, teleomorph: Pyrenophora) Species, including those in maize, grains such as barley (e.g., D. teres, reticulosis) and wheat (e.g., D. tritici-repentis: yellowish-brown spot)), rice and grass; in grapes, Formitiporia punctata (synonymous with Phellinus), F. mediterranea, and Phaeomoniella chlamydospora. Esca disease (canker, apoplexy) caused by chlamydospora (formerly Phaeoacremonium chlamydosporum), Phaeoacremonium aleophilum and / or Botryosphaeria obtusa; Elsinoe species, in pear-like fruits (E. pyri) and soft fruits (E. veneta: anthracnose) and grapes (E. amperina (E.ampelina: anthracnose; Entyloma oryzae (sooty mold) in rice; Epicoccum (black mold) in wheat; Erysiphe (powdery mildew), including those in sugar beets (E. betae), vegetables (e.g., E. pisi), cucurbits (e.g., E. cichoracearum), and cabbage and rapeseed (e.g., E. cruciferarum); Eutypa lata (Eutypa ulcer or canker, anamorph: Cytosporina lata, Libertella brepharis) in fruit trees, grapes and ornamental trees. Synonymous with blepharis); Exserohilum species (synonymous with Helminthosporium) in maize (e.g., E. turcicum); Fusarium species (teleomorph: Gibberella) in various plants (damping-off, root or stem rot), for example F. graminearum or F. culmorum in cereals (e.g., wheat or barley) (root rot, black spot or red mold); F. oxyphyll in tomatoes F. oxysporum, F. solani (synonymous with F. sp. glycines, now known as F. virguliforme), F. tucumaniae, and F. brasiliense, which each cause sudden death syndrome in soybeans, as well as F. verticillioides in maize; Gaeumannomyces graminis (damping-off disease) in cereals (e.g., wheat or barley) and maize; Gibberella species, including those in cereals (e.g., G. zeae) and those in rice (e.g., G. fusiliense).Fujikuroi (a type of rot), Bakanae disease; Glomerella cingulata in grapes, pears, and other plants, and G. gossypii in cotton; grain stain complex disease in rice; Guignardia bidwellii (black rot) in grapes; Gymnosporangium species in Rosaceae plants and junipers, such as G. sabinae (rust) in pears; Helminthosporium (synonymous with Drechslera, teleomorph: Cochliobolus) in maize, grains, potatoes, and rice; Hemileia species, such as H. vastatrix in coffee (coffee leaf rust); Isariopsis clavispora (synonymous with Cladosporium vitis) in grapes; and Macrophomina phaseolina in soybeans and cotton. Phaseolina (synonymous with phaseoli) (root and stem rot); Microdochium nivale (synonymous with Fusarium) (pink snow mold) in cereals (e.g., wheat or barley); Microsphaera diffuser in soybeans. Diffusa) (powdery mildew); Monilinia species in berries and other Rosaceae plants, e.g., M. laxa, M. fructicola and M. fructigena (synonymous with Monilia: flower blight and branch blight, brown rot); Mycosphaerella species in grains, bananas, soft fruits and peanuts, e.g., M. graminicola in wheat (anamorph: Zymoseptoria tritici, formerly Septoria tritici: Septoria leaf spot) or M. fijiensis in banana (Pseudocercospora fijiensis) Synonymous with fijiensis: black sigatoka disease) and M. musicola, M. arachidicola (synonymous with M. arachidis or Cercospora arachidis), M. berkeleyi in peanuts, M. in peas.Pisi and Brassiciola in Brassicaceae plants; Peronospora species (downy mildew), in cabbage (e.g., P. brassicae), rapeseed (e.g., P. parasitica), onion (e.g., P. destroyer), tobacco (P. tabacina), and soybean (P. manshurica); Phakopsora pachyridi in soybeans. P. pachyrhizi) and P. meibomiae (soybean rust); Phialophora species, for example in grapes (e.g., P. tracheiphila and P. tetraspora) and in soybeans (e.g., P. gregata: stem rot); Phoma lingam in rapeseed and cabbage (synonymous with Leptosphaeria biglobosa and L. maculans: root and stem rot); P. betae in sugar beets (root rot, leaf spot and seedling blight); and P. zeae-maydis in maize (Phyllostica zeae). Synonymous with zeae); Phomopsis species, such as those in sunflowers and grapes (e.g., P. viticola: leaf spot disease) and soybeans (e.g., stem rot: P. phaseoli, teleomorph: Diaporthe phaseolorum); Physoderma maydis (brown spot disease) in maize; Phytophthora species in various plants (damping-off disease, root, leaf, fruit and stem rot), such as those in paprika and cucurbitaceous plants (e.g., P. capsici), and soybeans (e.g., P.Plasmodiophora brascae (synonymous with megasperma, P. sojae), in potatoes and tomatoes (e.g., P. infestans: leaf blight), and in deciduous trees (e.g., P. ramorum: sudden death of oak); in cabbage, rapeseed, radish and other plants. Brassicae (club root disease); Plasmopara species, e.g., P. viticola (grape downy mildew) in grapes and P. halstedii in sunflowers; Podosphaera species (powdery mildew) in Rosaceae plants, hops, pears and soft fruits (e.g., P. leucotricha in apples) and in Cucurbitaceae plants (P. xanthii); Polymyxa species, e.g., in cereals, e.g., barley and wheat (P. graminis) and in sugar beets (P. betae) and the viral diseases transmitted thereby; Pseudocercosporella herpotrichoides in cereals, e.g., wheat or barley herpotrichoides) (synonymous with Oculimacula yallundae, O. acuformis: eye spot disease, teleomorph: Tapesia yallundae); Pseudoperonospora (downy mildew) in various plants, e.g. P. cubensis in cucurbitaceae or P. humili in hops; Pseudopezicula tracheiphila (red fireworks or rotbrenner, anamorph: phialophora) in grapes; Puccinia (rust) in various plants, P. triticina (P.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), P. kuehnii (orange rust) in sugarcane and P. asparagi in asparagus; P. pyrenopeziza in rapeseed Species of Pyrenopeziza, e.g., P. brassicae; Pyrenophora (anamorph: Drechslera) · tritici-repentis (yellowish-brown spot disease) in wheat or P. teres (net-like spot disease) in barley; species of Pyricularia, e.g., P. oryzae (teleomorph: Magnaporte · glycea) in rice. P. grisea (rice rot disease) and P. grisea in grass and cereals; Pythium species (seedling blight) (e.g., P. ultimum or P. aphanidermatum) in grass, rice, maize, wheat, cotton, rapeseed, sunflower, soybean, sugar beet, vegetables and various other plants; and P. oligandrum in mushrooms; Ramularia species, for example, R. collo-cygni (Ramularia leaf spot disease, physiological leaf spot disease) in barley, and R. areola (Teleomorph: Mycosphaerella areola) in cotton. Rhizoctonia species in cotton, rice, potato, grass, maize, rapeseed, potatoes, sugar beets, vegetables and various other plants, such as R. solani in soybeans (root and stem rot), and R. solani in rice.Solani) (sheath blight) or R. cerealis (Rhizoctonia spring blight) in wheat or barley; Rhizopus stolonifer (black mold, soft rot) in strawberries, carrots, cabbage, grapes and tomatoes; Rhynchosporium secalis and R. commune (burn disease) in barley, rye and rye; Sarocladium oryzae in rice S. oryzae) and S. attenuatum (shedd rot); Sclerotinia species (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 (synonymous with Athelia rolfsii) in soybeans, peanuts, vegetables, maize, grains and ornamental plants; Septoria species in various plants, such as S. glycines (brown spot) in soybeans, and S. tritici (wheat leaf blight) in wheat (Zymoseptoria (Synonymous with tritici, Septoria spot disease) and S. (Synonymous with Stagonospora) nodorum (Stagonospora spot disease) in cereals; Uncinula (Synonymous with Erysiphe) necator (Powdery mildew, anamorph: Oidium tuckeri) in grapes; Setosphaeria (Black leaf blight) in maize (e.g., S. turcicum, synonymous with Helminthosporium turcicum) and in turfgrass; Sphacelotheca (Sooty mold) in maize (e.g., S. reiliana (S.reiliana): Synonymous with Ustilago reiliana (smut), found in grains and sugarcane; Sphaerotheca fuliginea (synonymous with Podosphaera xanthii: powdery mildew) in cucurbitaceous plants. Spongospora subterranea (powdery crusting) and the viral diseases transmitted therefrom in potatoes; Stagonospora species in cereals, such as S. nodorum in wheat (Stagonospora spot disease, teleomorph: synonymous with Leptospheria [Phaeosphaeria] nodorum, synonymous with Septoria nodorum); Synchytrium endobioticum in potatoes. (endobioticum) (potato wart); 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 (synonymous with Chalara elegans); Tilletia species (common or smut) in cereals, e.g., T. tritici (synonymous with T. caries, smut) and T. controversa (dwarf smut) in wheat; Trichoderma halzianum in mushrooms harzianum); Typhula incarnata (gray snow mold) in barley or wheat; Urocystis species, e.g., U. occulta (sooty stripe disease) in rye; Uromyces species (rust disease) in vegetables, e.g., those in legumes (e.g., synonymous with U. appendiculatus, U. phaseoli), those in sugar beets (e.g., U. betae or U. beticola) and leguminous plants (e.g., U. vignae, U. pisi, U. viciae-fabae) and U. fabae (U.fabae); Ustilago species (naked smut), which are found in cereals (e.g., U. nuda and U. avaenae), maize (e.g., U. maydis: maize sooty mold) and sugarcane; Venturia species (black spot), which are found in apples (e.g., V. inaequalis) and pears This includes various plants, such as fruit and ornamental plants, grapes, soft fruits, vegetables, and crops, specifically Verticillium species (damping-off disease), such as V. longisporum in rapeseed, V. dahliae in strawberries, rapeseed, potatoes, and tomatoes, and V. fungicola in mushrooms; and the wheat leaf blight fungus (Zymoseptoria tritici) in cereals.

[0203] Compound I and its compositions are particularly suitable for controlling the following plant disease-causing substances: rust diseases of soybeans and grains (e.g., Phakopsora pachyrhizi and P. meibomiae of soybeans, Puccinia tritici and P. striiformis of wheat); fungal diseases of special crops, soybeans, rapeseed and sunflowers (e.g., Botrytis cinerea of ​​strawberries and grapes, Sclerotinia sclerotiorum, S. minor and S. rolfsii of rapeseed, sunflowers and soybeans); Fusarium disease of grains (e.g., Fusarium crumorum of wheat) F. culmorum and F. graminearum); downy mildew of specialty crops (e.g., Plasmopara viticola in grapes, Phytophthora infestans in potatoes); powdery mildew of specialty crops and grains (e.g., Uncinula necator in grapes, Erysiphe spp. in various specialty crops, Blumeria graminis in grains); leaf spot diseases of cereals, soybeans and maize (e.g., Septoria tritici and S. nodorum in cereals, S. glycines in soybeans, Cercospora spp. in maize and soybeans).

[0204] According to one embodiment, compounds IA-1.1aB-1 to IA-1.1aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0205] According to one embodiment, compounds IA-2.1aB-1 to IA-2.1aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0206] According to one embodiment, compounds IA-3.1aB-1 to IA-3.1aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0207] According to one embodiment, compounds IA-4.1aB-1 to IA-4.1aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0208] According to one embodiment, compounds IA-1.2aB-1 to IA-1.2aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0209] According to one embodiment, compounds IA-2.2aB-1 to IA-2.2aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0210] According to one embodiment, compounds IA-3.2aB-1 to IA-3.2aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0211] According to one embodiment, compounds IA-4.2aB-1 to IA-4.2aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0212] According to one embodiment, compounds IA-1.3aB-1 to IA-1.3aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0213] According to one embodiment, compounds IA-2.3aB-1 to IA-2.3aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0214] According to one embodiment, compounds IA-3.3aB-1 to IA-3.3aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0215] According to one embodiment, compounds IA-4.3aB-1 to IA-4.3aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0216] According to one embodiment, compounds IA-1.4aB-1 to IA-1.4aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0217] According to one embodiment, compounds IA-2.4aB-1 to IA-2.4aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0218] According to one embodiment, compounds IA-3.4aB-1 to IA-3.4aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases listed in Z.

[0219] According to one embodiment, compounds IA-4.4aB-1 to IA-4.4aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0220] According to one embodiment, compounds IA-1.5aB-1 to IA-1.5aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0221] According to one embodiment, compounds IA-2.5aB-1 to IA-2.5aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0222] According to one embodiment, compounds IA-3.5aB-1 to IA-3.5aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0223] According to one embodiment, compounds IA-4.5aB-1 to IA-4.5aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0224] According to one embodiment, compounds IA-1.6aB-1 to IA-1.6aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0225] According to one embodiment, compounds IA-2.6aB-1 to IA-2.6aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0226] According to one embodiment, compounds IA-3.6aB-1 to IA-3.6aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0227] According to one embodiment, compounds IA-4.6aB-1 to IA-4.6aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0228] According to one embodiment, compounds IA-1.7aB-1 to IA-1.7aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0229] According to one embodiment, compounds IA-2.7aB-1 to IA-2.7aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0230] According to one embodiment, compounds IA-3.7aB-1 to IA-3.7aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0231] According to one embodiment, compounds IA-4.7aB-1 to IA-4.7aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0232] According to one embodiment, compounds IB-1.1aB-1 to IB-1.1aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0233] According to one embodiment, compounds IB-2.1aB-1 to IB-2.1aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0234] According to one embodiment, compounds IB-3.1aB-1 to IB-3.1aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0235] According to one embodiment, compounds IB-4.1aB-1 to IB-4.1aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0236] According to one embodiment, compounds IB-1.2aB-1 to IB-1.2aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0237] According to one embodiment, compounds IB-2.2aB-1 to IB-2.2aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0238] According to one embodiment, compounds IB-3.2aB-1 to IB-3.2aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0239] According to one embodiment, compounds IB-4.2aB-1 to IB-4.2aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0240] According to one embodiment, compounds IB-1.3aB-1 to IB-1.3aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0241] According to one embodiment, compounds IB-2.3aB-1 to IB-2.3aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0242] According to one embodiment, compounds IB-3.3aB-1 to IB-3.3aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0243] According to one embodiment, compounds IB-4.3aB-1 to IB-4.3aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0244] According to one embodiment, compounds IB-1.4aB-1 to IB-1.4aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0245] According to one embodiment, compounds IB-2.4aB-1 to IB-2.4aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0246] According to one embodiment, compounds IB-3.4aB-1 to IB-3.4aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0247] According to one embodiment, compounds IB-4.4aB-1 to IB-4.4aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0248] According to one embodiment, compounds IB-1.5aB-1 to IB-1.5aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0249] According to one embodiment, compounds IB-2.5aB-1 to IB-2.5aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0250] According to one embodiment, compounds IB-3.5aB-1 to IB-3.5aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0251] According to one embodiment, compounds IB-4.5aB-1 to IB-4.5aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0252] According to one embodiment, compounds IB-1.6aB-1 to IB-1.6aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0253] According to one embodiment, compounds IB-2.6aB-1 to IB-2.6aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0254] According to one embodiment, compounds IB-3.6aB-1 to IB-3.6aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0255] According to one embodiment, compounds IB-4.6aB-1 to IB-4.6aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0256] According to one embodiment, compounds IB-1.7aB-1 to IB-1.7aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0257] According to one embodiment, compounds IB-2.7aB-1 to IB-2.7aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0258] According to one embodiment, compounds IB-3.7aB-1 to IB-3.7aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0259] According to one embodiment, compounds IB-4.7aB-1 to IB-4.7aB-25 are particularly suitable for controlling the pathogenic factors of plant diseases as listed in Z.

[0260] According to one embodiment, compounds Ex-1 to Ex-101 are particularly suitable for controlling the pathogenic factors of plant diseases listed in Z.

[0261] List Z: Albugo (white rust disease) in ornamental plants, vegetables (e.g., A. candida) and sunflowers (e.g., A. tragopogonis); Alternaria (black spot disease) in vegetables (e.g., A. dauci or A. porri), rapeseed (e.g., A. brassicicola or A. brassicae), sugar beets (A. tenuis), fruits (e.g., A. grandis), rice, soybeans, potatoes and tomatoes. Those found in (e.g., A. solani, A. grandis, or A. alternata), those in tomatoes (e.g., A. solani or A. alternata), and those in wheat (e.g., A. triticina); Aphanomyces species found in sugar beets and vegetables; Ascochyta species in cereals and vegetables, e.g., A. tritici (anthracnose) in wheat and A. hordei in barley; Aureobasidium in maize. zeae) (synonymous with maize brown spot (Kapatiella zeae); Bipolaris and Drechslera species (Teleomorph: Cochliobolus species), for example, sesame leaf spot (D. maydis) or sooty spot (B. zeicola) in maize, for example, spot disease (B. sorokiniana) in cereals, for example, B. oryzae (B.oryzae; Blumeria (formerly Erysiphe) graminis (powdery mildew) in cereals (e.g., wheat or barley); gray mold (Botrytis cinerea) (teleomorph: Botryotinia fuckeliana: gray mold) in fruits and berries (e.g., strawberries), 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), grapes, forest plants and wheat; Bremia lactucae in lettuce lactucae) (downy mildew); Ceratocystis (synonymous with Ophiostoma) species (root rot or damping-off disease) in deciduous and evergreen trees, for example C. ulmi (Ulmus ulmi) in elm; Cercospora species (Cercospora spot disease), and maize (for example, gray spot: C. zeae-maydis), rice, sugar beet (for example, C. Those found in beticola, sugarcane, vegetables, coffee, soybeans (e.g., C. sojina or C. kikuchii), and rice; Cladobotryum species (synonymous with Dactylium) in mushrooms (e.g., C. mycophilum) (formerly Dactylium dendroides) dendroides, teleomorph: Nectria albertinii, Nectria rosella (synonymous with Hypomyces rosellus); Cladosporium species, such as those in tomatoes (e.g., C. fulvum: leaf mold) and those in grains, such as C. herbarum in wheat (C.herbarum) (black spot disease); Claviceps purpurea (corn rot) in cereals; Cochliobolus (anamorph: Helminthosporium of Bipolaris) species (spot disease), including those in maize (C. carbonum), cereals (e.g., C. sativus, anamorph: B. sorokiniana) and rice ( For example, C. miyabeanus (anamorph: H. oryzae); Colletotricum (teleomorph: Glomerella) species (anthracnose), which are found in cotton (e.g., C. gossypii), in maize (e.g., C. graminicola: anthracnose root rot), in soft fruit, and in potatoes. (e.g., C. coccodes: black spot disease), those found in legumes (e.g., C. lindemuthianum), soybeans (e.g., C. truncatum or C. gleosporioides), vegetables (e.g., C. lagenarium or C. capsici), fruits (e.g., C. actatum) (C. acutatum)), C. gloeosporioides in coffee (e.g., C. coffeanum or C. kahawae) and in various crops; Corticium species in rice, e.g., C. sasakii (sheath blight); Corynespora cassiicola (leaf spot) in soybeans, cotton and ornamental plants; Cycloconium species, e.g., C. oleaginum (C.oleaginum); Cylindrocarpon (e.g., fruit tree ulcer disease or weakness of young grapes, teleomorph: Nectria or Neonectria) in fruit trees, in grapes (e.g., C. liriodendri, teleomorph: Neonectria liriodendri) (Liriodendri), black foot disease, and those in ornamental plants; Dematophora (teleomorph: Roselinia) and Necatrix (root and stem rot) in soybeans; Diaporthe species in soybeans, e.g., D. phaseolorum (seedling blight); Dreshlera (synonymous with Helminthosporium, teleomorph: Pyrenophora) Species, including those in maize, grains such as barley (e.g., D. teres, reticulosis) and wheat (e.g., D. tritici-repentis: yellowish-brown spot)), rice and grass; in grapes, Formitiporia punctata (synonymous with Phellinus), F. mediterranea, and Phaeomoniella chlamydospora. Esca disease (canker, apoplexy) caused by chlamydospora (formerly Phaeoacremonium chlamydosporum), Phaeoacremonium aleophilum and / or Botryosphaeria obtusa; Elsinoe species, in pear-like fruits (E. pyri) and soft fruits (E. veneta: anthracnose) and grapes (E. amperina (E.ampelina: anthracnose; Entyloma oryzae (sooty mold) in rice; Epicoccum (black mold) in wheat; Erysiphe (powdery mildew), including those in sugar beets (E. betae), vegetables (e.g., E. pisi), cucurbits (e.g., E. cichoracearum), and cabbage and rapeseed (e.g., E. cruciferarum); Eutypa lata (Eutypa ulcer or canker, anamorph: Cytosporina lata, Libertella brepharis) in fruit trees, grapes and ornamental trees. Synonymous with blepharis); Exserohilum species (synonymous with Helminthosporium) in maize (e.g., E. turcicum); Fusarium species (teleomorph: Gibberella) in various plants (damping-off, root or stem rot), for example F. graminearum or F. culmorum in cereals (e.g., wheat or barley) (root rot, black spot or red mold); F. oxyphyll in tomatoes F. oxysporum, F. solani (synonymous with F. sp. glycines, now known as F. virguliforme), F. tucumaniae, and F. brasiliense, which each cause sudden death syndrome in soybeans, as well as F. verticillioides in maize; Gaeumannomyces graminis (damping-off disease) in cereals (e.g., wheat or barley) and maize; Gibberella species, including those in cereals (e.g., G. zeae) and those in rice (e.g., G. fusiliense).Fujikuroi (a type of rot), Bakanae disease; Glomerella cingulata in grapes, pears, and other plants, and G. gossypii in cotton; Corn stain complex disease in rice; Guignardia bidwellii (black rot) in grapes; Gymnosporangium species in Rosaceae plants and junipers, e.g., G. sabinae (rust) in pears; Helminthosporium species in maize, cereals, potatoes, and rice (synonymous with Dreshlera, teleomorph: Cochliobolus); Hemileia species, for example, H. vastatrix in coffee (coffee leaf rust); Isariopsis clavispora in grapes (synonymous with Cladosporium vitis); Macrophomina phaseolina in soybeans and cotton (synonymous with phaseoli) (root and stem rot); Microdochium nivale (synonymous with Fusarium) in cereals (e.g., wheat or barley) (pink snow mold); Microsphaera diffuser in soybeans Diffusa) (powdery mildew); Monilinia species in berries and other Rosaceae plants, e.g., M. laxa, M. fructicola and M. fructigena (synonymous with Monilia: flower blight and branch blight, brown rot); Mycosphaerella species in grains, bananas, soft fruits and peanuts, e.g., M. graminicola in wheat (anamorph: Zymoseptoria tritici, formerly Septoria tritici: Septoria leaf spot) or M. fijiensis in banana (Pseudocercospora fijiensis) Synonymous with fijiensis: black sigatoka disease) and M. musicola, M. arachidicola (synonymous with M. arachidis or Cercospora arachidis), M. berkeleyi in peanuts, M. pisi in peas and M. brassiciola in Brassicaceae plants; Peronospora species (downy mildew), which is found in cabbage (for example, P. brassicae (P.Brassicae), in rapeseed (e.g., P. parasitica), in onions (e.g., P. destroyer), in tobacco (P. tabacina), and in soybeans (P. manshurica); in soybeans, Phakopsora pachyrhizi and P. meibomiae (soybean rust); in phialophora species, for example, in grapes (e.g., P. tracheiphila and P. tetraspora) and in soybeans (e.g., P. gregata: stem rot); in rapeseed and cabbage, Phoma lingham. P. lingam) (synonymous with Leptosphaeria biglobosa and L. maculans: root and stem rot) and P. betae in sugar beets (root rot, leaf spot, and seedling blight) and P. zeae-maydis in maize (synonymous with Phyllostica zeae); Phomopsis species in sunflowers and grapes (e.g., P. viticola: leaf spot) and in soybeans (e.g., stem rot: P. phaseoli, teleomorph: Diaporthe phaseolorum); Physoderma maize in maize Maydis (brown spot disease); Phytophthora species in various plants (damping-off, root, leaf, fruit and stem rot), for example, in paprika and cucurbits (e.g., P. capsici), in soybeans (e.g., P. megasperma, synonymous with P. sojae), in potatoes and tomatoes (e.g., P. infantans: leaf rot), and in deciduous trees (e.g., P.Plasmodiophora ramorum: sudden death of oak; Plasmodiophora brassicae in cabbage, rapeseed, radish and other plants. Brassicae (club root disease); Plasmopara species, e.g., P. viticola (grape downy mildew) in grapes and P. halstedii in sunflowers; Podosphaera species (powdery mildew) in Rosaceae plants, hops, pears and soft fruits (e.g., P. leucotricha in apples) and in Cucurbitaceae plants (P. xanthii); Polymyxa species, e.g., in cereals, e.g., barley and wheat (P. graminis) and in sugar beets (P. betae) and the viral diseases transmitted thereby; Pseudocercosporella herpotrichoides in cereals, e.g., wheat or barley herpotrichoides) (synonymous with Oculimacula yallundae, O. acuformis: eye spot disease, teleomorph: Tapesia yallundae); Pseudoperonospora (downy mildew) in various plants, for example P. cubensis in cucurbitaceae or P. humili in hops; Pseudopezicula tracheiphylla in grapes P. tracheiphila) (red fire blight or rotbrenner, anamorph: phialophora); Puccinia species (rust) in various plants, 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 in rapeseed, e.g., P. brassicae; P. in wheat Pyrenophora (anamorph: Drechslera) · tritici-repentis (yellowish-brown spot disease) or P. teres (reticulated spot disease) in barley; Pyricularia species, for example, P. oryzae (teleomorph: Magnaporte glycea) in rice. P. grisea (rice rot disease) and P. grisea in grass and cereals; Pythium species (seedling blight) (e.g., P. ultimum or P. aphanidermatum) in grass, rice, maize, wheat, cotton, rapeseed, sunflower, soybean, sugar beet, vegetables and various other plants; and P. oligandrum in mushrooms; Ramularia species, for example, R. collo-cygni (Ramularia leaf spot disease, physiological leaf spot disease) in barley, and R. areola (Teleomorph: Mycosphaerella areola) in cotton. Rhizoctonia species in cotton, rice, potato, grass, maize, rapeseed, potatoes, sugar beets, vegetables and various other plants, such as 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, grapes and tomatoes; Rhynchosporium secalis and R. commune (burn disease) in barley, rye and rye; Sarocladium oryzae in rice S. oryzae) and S. attenuatum (shedd rot); Sclerotinia species (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 (synonymous with Athelia rolfsii) in soybeans, peanuts, vegetables, maize, grains and ornamental plants; Septoria species in various plants, such as S. glycines (brown spot) in soybeans, and S. tritici (wheat leaf blight) in wheat (Zymoseptoria (Synonymous with tritici, Septoria spot disease) and S. (Synonymous with Stagonospora) nodorum (Stagonospora spot disease) in cereals; Uncinula (Synonymous with Erysiphe) necator (Powdery mildew, anamorph: Oidium tuckeri) in grapes; Setosphaeria (Black leaf blight) in maize (e.g., S. turcicum, synonymous with Helminthosporium turcicum) and in turfgrass; Sphacelotheca (Sooty mold) in maize (e.g., S. reiliana (S.reiliana): Synonymous with Ustilago reiliana (smut), affecting grains and sugarcane; Sphaerotheca fuliginea (synonymous with Podosphaera xanthii: powdery mildew) in cucurbits; Spongospora subterranea (spore-forming crusting disease) in potatoes and the viral diseases transmitted by it; Stagonospora species in cereals, e.g., S. nodorum in wheat (Stagonospora spot disease, teleomorph: synonymous with Leptospheria [Phaeosphaeria] nodorum, synonymous with Septoria nodorum); Synchytrium endobioticum in potatoes (potato wart disease); Taphrina species, e.g., T. deformans in peaches (leaf curl disease) and T. pruni in plums (pocket plum disease); Thielaviopsis species in tobacco, pears, vegetables, soybeans and cotton (black root rot), e.g., T. basicola (Chalara elegans) (Synonymous with elegans); Tilletia species in cereals (common or smut disease), for example, T. tritici (synonymous with T. caries, smut disease) and T. controversa (dwarf smut disease) in wheat; Trichoderma harzianum in mushrooms; Typhula incarnata in barley or wheat. incarnata) (gray snow mold); Urocystis species, for example U. occulta (sooty stripe disease) in rye; Uromyces species (rust disease) in vegetables, for example those in legumes (e.g., synonymous with U. appendiculatus and U. phaseoli), those in sugar beets (e.g., U. betae or U. beticola) and legumes (e.g., U. vignae, U. pisi, U. viciae-fabae and U. fabae); Ustilago species (naked smut) in cereals (e.g., U. nuda and U. abaenae).(avaenae), those found in maize (e.g., U. maydis: maize sooty mold) and sugarcane; Venturia species (black spot disease), those found in apples (e.g., V. inaequalis) and pears; and Verticillium species (damping-off disease) in various plants, such as fruits and ornamental plants, grapes, 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 wheat leaf spot disease fungus (Zymoseptoria tritici) in cereals.

[0262] 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.

[0263] The term “storage products or harvested products” is understood to refer to 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. Wood that falls under the definition of storage products can also be in the form of rough timber, such as construction timber, steel towers, and barriers, or in the form of finished products, such as furniture or objects made from wood. Animal-derived storage products include hides, leather, fur, and hair. Preferably, “storage products” is understood to refer to natural substances of plant origin and their processed forms, more preferably fruits and their processed forms, such as fruits, pebbles, melamines, 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.

[0264] The term "material protection" is understood to mean protecting 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.

[0265] When used for the protection of materials or stored products, the application rate of the active substance varies depending on the application area and the type of effect desired. A typical application rate for material protection is 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of the active substance per cubic meter of the material being treated.

[0266] Compound I and its compositions can each be used to improve plant health. The present invention also relates to a method of 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.

[0267] The term “plant health” is understood to describe the state of a plant and / or its products, determined by several indicators, individually or in combination with each other, such as yield (e.g., increased biomass and / or increased content of valuable 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 identified indicators of plant health described above may be interdependent or attributable to each other.

[0268] 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 to be protected from fungal attack, with a bactericidal 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.

[0269] The pesticide composition of the present invention contains a fungicidal amount of compound I. The term "fungicidal amount" refers to an amount of composition or compound I that is sufficient to control harmful fungi on cultivated plants or to protect stored products, harvested products, or materials, without causing substantial damage to the treated plants, treated stored products, harvested products, or materials. Such an amount can vary widely and depends on various factors such as the species of fungus to be controlled, the treated cultivated plants, stored products, harvested products, or materials, climatic conditions, and the specific compound I used.

[0270] Plant propagation material may be treated either as is or preventively with a composition containing at least one compound I at the time of planting or transplanting, or immediately before.

[0271] When used for plant disease control, the amount of active substance applied is 0.001 to 2 kg / ha, preferably 0.005 to 2 kg / ha, more preferably 0.05 to 0.9 kg / ha, and particularly 0.1 to 0.75 kg / ha, depending on the type of effect desired.

[0272] 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).

[0273] The user typically applies the product from a device that allows for pre-setting of the dosage, a backpack sprayer, a spray tank, a spray aircraft, or an irrigation system. Typically, the pesticide composition is brought to the desired application concentration with water, a buffer, and / or further additives, thus obtaining a ready-to-use spray solution or pesticide composition according to the present invention. Typically, the prepared spray solution is applied at a rate of 20 to 2000 liters, preferably 50 to 400 liters, per hectare of agrochemically useful area.

[0274] Compound I, its N-oxides, and salts can be converted into conventional types of pesticide compositions, such as solutions, emulsions, suspensions, dusts, 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, pastilles, wettable powders or dusts (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 in Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005. The present invention also relates to an agricultural chemical composition comprising an auxiliary agent and at least one compound I.

[0275] 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.

[0276] 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., lactates, carbonates, fatty acid esters, γ-butyrolactone; fatty acids; phosphonates; amines; amides, e.g., N-methylpyrrolidone, fatty acid dimethylamide; and mixtures thereof.

[0277] Suitable solid carriers or fillers include mineral soils such as silicate, silica gel, talc, kaolin, limestone, lime, chalk, clay, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides such as cellulose, starch; fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea; plant-derived products such as grain meal, bark meal, wood meal, nut shell meal, and mixtures thereof.

[0278] Suitable surfactants are surfactant compounds such as anionic, cationic, nonionic, and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifiers, dispersants, solubilizers, wetting agents, penetration enhancers, protective colloids, or adjuvants. Examples of surfactants are listed in McCutcheon's, Vol. 1: Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).

[0279] 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, α-olefin sulfonates, lignin sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of 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 are phosphate esters. Examples of carboxylates are alkyl carboxylates and carboxylated alcohols or alkylphenol ethoxylates.

[0280] 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, are 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.

[0281] 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 containing blocks of polyethylene oxide and polypropylene oxide, or ABC type block polymers containing alkanols, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamine or polyethyleneamine.

[0282] Suitable adjuvants are compounds that themselves have negligibly low or no insecticidal activity and enhance 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.

[0283] Suitable thickeners include polysaccharides (e.g., xanthan gum, carboxymethylcellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates.

[0284] Suitable fungicides include bronopol and isothiazolinone derivatives, such as alkylisothiazolinone and benzisothiazolinone.

[0285] Suitable antifreezes are ethylene glycol, propylene glycol, urea, and glycerin.

[0286] Suitable defoaming agents include silicones, long-chain alcohols, and fatty acid salts.

[0287] Suitable colorants (e.g., red, blue, or green) are pigments with low water solubility and water-soluble dyes. Examples include inorganic colorants (e.g., iron oxide, titanium dioxide, iron hexacyano) and organic colorants (e.g., alizarin colorants, azo colorants, and phthalocyanine colorants).

[0288] Suitable tackifiers or binders include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, polyacrylate, biological or synthetic waxes, and cellulose ethers.

[0289] 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).

[0290] For the treatment of plant propagation materials, particularly seeds, commonly used formulations include seed treatment solutions (LS), sasporumulants (SE), fluid concentrates (FS), drying powders (DS), water-dispersible powders (WS), water-soluble powders (SS), emulsions (ES), emulsifying concentrates (EC), and gels (GF). The compositions in question provide an active substance concentration of 0.01 to 60% by weight, preferably 0.1 to 40%, in formulations that can be used immediately after dilution 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, dipping, and in-sowing application. 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.

[0291] Various oils, wetting agents, adjuvants, fertilizers or micronutrients and further pesticides (e.g., fungicides, growth regulators, herbicides, insecticides, mitigants) may be added to Compound I or its composition as a premix, or they may not be mixed until immediately before use (tank mixing). 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.

[0292] Pesticides are generally chemical or biological agents (such as biocides, compounds, compositions, viruses, bacteria, antimicrobial agents, and fungicides) that suppress, neutralize, kill, or otherwise eliminate pests by their effects. 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" also includes plant growth regulators that alter the expected growth, flowering, or reproduction rate of plants; 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 tips; plant activators that activate plant physiology for defense against specific pests; antidotes that mitigate the undesirable herbicidal effects of pesticides on crop plants; and plant growth promoters that affect plant physiology to increase, for example, plant growth, biomass, yield, or other quality parameters of the harvestable products of crop plants.

[0293] Biocides are defined as a form of pesticide based on microorganisms (bacteria, fungi, viruses, nematodes, etc.) or natural products (biological or other naturally occurring compounds, e.g., metabolites, proteins, or extracts) (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 multicellular, but are classified as microbial pesticides. (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.

[0294] By mixing compound I, or compositions containing it, in their form as a fungicide, with other fungicides, it is often possible to broaden the fungicidal spectrum of activity or prevent the development of fungicide resistance. Furthermore, synergistic effects are often obtained (synergistic mixtures).

[0295] 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.

[0296] A) Respiratory inhibitors - Q oInhibitors of complex III at the site: azoxystrobin (A.1.1), cumetoxystrobin (A.1.2), chemoxystrobin (A.1.3), dimoxystrobin (A.1.4), enestrobrin (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), metmino Strobin (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), Pyribe Ncarb (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-methyl Toxyimino-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-methoxyacrylate methyl ester (A.1.38); - Q iInhibitors of complex III at the site: 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), benzovindiflupyr (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), fraxapyroxade (A.3.9), flametopyr (A.3.10), isofetamide (A.3.11), isopyrazam (A.3.12), mepronil (A.3.13), oxycarboxyne (A.3.14), penflufen (A.3.15), pe Nthiopyrad (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), Pirapropoin (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-4-yl)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 (A.3.34)-pyridine-3-carboxamide (A.3.35), 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethylindan-4-yl]pyridine-3-carboxamide (A.3.36), 2-(difluoromethyl)-N-(1,1-dimethyl-3-propylindan-4-yl)pyridine-3-carboxamide (A.3.36)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).

[0297] 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.1.1) .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 Zole (B.1.26), triadimefone (B.1.27), triadimenol (B.1.28), triticonazole (B.1.29), uniconazole (B.1.30), 2-(2,4-difluorophenyl)-1,1-difluoro-3-(tetrazole-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-( Tetrazole-1-yl)-1-[5-[4-(trifluoromethoxy)phenyl]-2-pyridyl]propan-2-ol (B.1.32), 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-sulfanyl-1,2,4-triazole-1-yl)propyl]-3-pyridyl]oxy]benzonitrile (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-Tolyl-methyl)-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), Trifo Phosphorus (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]benzoni Tolyl (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);. - Delta-14-reductase inhibitors: Algimorph (B.2.1), Dodemorph (B.2.2), Dodemorph-acetate (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 inhibitor: Fenhexamide (B.3.1); - Other sterol biosynthesis inhibitors: Chlorfenomizole (B.4.1).

[0298] 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-4amine (C.2.6), 5-Fluoro-2-(4-Fluorophenylmethoxy)pyrimidine-4amine (C.2.7), 5-Fluoro-2(4-Chlorophenylmethoxy)pyrimidine-4amine (C.2.8).

[0299] D) Inhibitors of cell division and the cytoskeleton - Tubulin inhibitors: Benomyl (D.1.1), Carbendazim (D.1.2), Fuberidazole (D1.3), 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).

[0300] 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).

[0301] 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).

[0302] G) Lipid and membrane synthesis inhibitors - Phospholipid biosynthesis inhibitors: edifenphos (G.1.1), iprobenphos (G.1.2), pyrazophos (G.1.3), isoprothiolane (G.1.4); - Lipid peroxidation: Dichlorane (G.2.1), Quintozene (G.2.2), Technazen (G.2.3), Torukurofos-methyl (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), flumorph (G.3.2), mandipropamide (G.3.3), pyrimorph (G.3.4), benthiavalicarb (G.3.5), iproavalicarb (G.3.6), valifenalate (G.3.7); - Compounds that affect cell membrane permeability and fatty acids: Propamocarb (G.4.1); - Inhibitors of oxysterol-binding proteins: 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).

[0303] 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), Maneb (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 and others: Guanidine (H.4.1), Dozin (H.4.2), Dozin free base (H.4.3), Guazatin (H.4.4), Guazatin acetate (H.4.5), Iminooctadine (H.4.6), Iminooctadine triacetate (H.4.7), Iminooctadine tris(albesylate) (H.4.8), Dithianone (H.4.9), 2,6-dimethyl-1H,5H-[1,4]ditino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetraone (H.4.10).

[0304] I) Cell wall synthesis inhibitors - Glucan synthesis inhibitors: validamycin (I.1.1), polyoxin B (I.1.2); - Melanin synthesis inhibitors: Pyrroquilon (I.2.1), Tricyclazole (I.2.2), Carpropamide (I.2.3), Dicyclomet (I.2.4), Phenoxanil (I.2.5).

[0305] J) Plant defense inducers - Acibenzolar-S-methyl (J.1.1), probenazole (J.1.2), isothianil (J.1.3), thiadinil (J.1.4), prohexadione-calcium (J.1.5); phosphonates: fosetyl (J.1.6), fosetyl-aluminum (J.1.7), phosphorous acid and its salts (J.1.8), calcium phosphate (J.1.11), potassium phosphate (J.1.12), potassium bicarbonate or sodium bicarbonate (J.1.9), 4-cyclopropyl-N-(2,4-dimethoxyphenyl)thiadiazole-5-carboxamide (J.1.10).

[0306] K) Mechanism of action unknown - Bronopol (K.1.1), Synomethionat (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), Diphenzoquat (K.1.9), Diphenzoquat-methylsulfate (K.1.10), Diphenylamine (K.1.11), Fenitropan (K.1.12), Fenpyrazamine (K.1.13), Flumetova (K.1.14), Fursulfamide (K .1.15), Fluthianil (K.1.16), Harbin (K.1.17), Metasulfocarb (K.1.18), Nitrapyrine (K.1.19), Nitrotal-isopropyl (K.1.20), Tolprocarb (K.1.21), Oxine-copper (K.1.22), Proquinazide (K.1.23), Tebufloquine (K.1.24), Tecrophthalam (K.1.25), Triazoxide (K.1.26), N'-(4-(4-chloro-3-trifluoromethyl-phenoxy)-2,5-dimethylphenyl)-N-ethyl-N -Methylformamidine (K.1.27), N'-(4-(4-fluoro-3-trifluoromethylphenoxy)-2,5-dimethylphenyl)-N-ethyl-N-methylformamidine (K.1.28), 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-propo-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-propo-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), Ipuflufenokine (K.1.44), Quinofumeline (K.1.47), Benziothiazolinone (K.1.48), Bromotalonyl (K.1.49), 2-(6-benzyl-2-pyridyl)quinazo Phosphorus (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-dichlorothiazole-2-yl)oxy-2,5-dimethylphenyl]-N-ethyl-N-methyl-formamidine (K.1.57), N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazole-3-yl]benzamide (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 (International Publication No. 2018 / 177894, International Publication No. 2020 / 212513).

[0307] L) Bio-pesticides L1) Microbial pesticides having fungicidal, bactericidal, virucidal activity and / or plant defense activator 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.Gliocladium catenulate (also known as Gliocladium catenulate), 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 activator activity: Harbin 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 subsp. israelensis, Bt subsp. galleriae, Bt subsp. kurstaki, Bt subsp. 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.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-yl acetate, ethyl formate, (E,Z)-2,4-ethyldecadienone (pear ester), (Z,Z,E)-7,11,13-hexadecatrienal, heptyl butyrate, isopropyl myristate, lavanulyl senesioate (lavanulyl (senecioate), cis-jasmon, 2-methyl-1-butanol, methyl eugenol, methyl jasmonate, (E,Z)-2,13-octadecadiene-1-ol, (E,Z)-2,13-octadecadiene-1-ol acetate, (E,Z)-3,13-octadecadiene-1-ol, (R)-1-octen-3-ol, pentatermanone, (E,Z,Z)-3,8,11-tetradecatrienylate acetate, (Z,E)-9,12-tetradecadiene-1-yl acetate, (Z)-7-tetradecen-2-one, (Z)-9-tetradecen-1-yl acetate, Z-11-tetradecenal, (Z)-11-tetradecen-1-ol, Aritasou (Chenopodium Ambrosiodes extract, catnip oil, neem oil, quillaya 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.

[0308] O) Insecticides of class O.1 to 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, Cadsaphos, Chlorethoxyphos, Chlorfenbinphos, Chlormephos, Chlorpyrifos, Chlorpyrifos-methyl, Coumaphos, Cyanophos, Demeton-S-methyl, Diazinon, Dichlorvos / DDVP, Diclotophos, Dimethoate, Dimethi Rubinphos, disulfon, EPN, ethione, etoprophos, famflu, phenamiphos, fenitrothion, fenthion, fostiazate, heptenophos, imisiaphos, isofenphos, isopropyl O-(methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monoclotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, fenthoate, phorate, fosalon, fosmet, phosphamidone, foxim, pyrimiphos-methyl, profenophos, propethamphos, prothiophos, pyraclophos, pyridaphenthion, quinalphos, sulfotep, tebupyrimphos, temephos, terbuphos, tetrachlorvinphos, thiometon, triazophos, trichlorfon, bamidothion.

[0309] O.2 GABA-gate chloride channel antagonists: endosulfan, chlordane; ethiprole, fipronil, flufiprole, pyrafluprole, pyriprole.

[0310] O.3 Sodium channel modulators: Acrinatrin, Arethrin, d-cis-transarethrin, d-transarethrin, bifenthrin, kappa-bifenthrin, bioarethrin, bioarethrin S-cyclopentenyl, violethmetrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, dita-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalere Etofenprox, fenpropathrin, fenvalerate, flucitrinate, flumethrin, tau-fluvalinate, halfenprox, heptafluthrin, imiprothrin, meperfluthrin, metofluthrin, momflufluorothrin, epsilon-momufluorothrin, permethrin, phenothrin, prallethrin, profluthrin, pyrethrin (chrysanthemum), resmethrin, silafluofen, tefluthrin, kappa-tefluthrin, tetramethylfluthrin, tetramethrin, tralomethrin, transfluthrin; DDT, methoxychloride.

[0311] 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 carboxyimidamide; 1-[(6-chloro [Pyridine-3-yl)methyl]-7-methyl-8-nitro-5-propoxy-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridine; nicotine; sulfoxaflor, flupyradiflon, triflumezopyrim, (3R)-3-(2-chlorothiazol-5-yl)-8-methyl-5-oxo-6-phenyl-2,3-dihydrothiazolo[3,2-a]pyrimidine-8-ium-7-oleate, (3S)-3-(6-chloro-3-pyrimidine) (zyl)-8-methyl-5-oxo-6-phenyl-2,3-dihydrothiazolo[3,2-a]pyrimidine-8-ium-7-oleate, (3S)-8-methyl-5-oxo-6-phenyl-3-pyrimidine-5-yl-2,3-dihydrothiazolo[3,2-a]pyrimidine-8-ium-7-oleate, (3R)-3-(2-chlorothiazol-5-yl)-8-methyl-5-oxo-6-[3-(trifluoromethyl)phenyl]-2,3-dihydro Thiazolo[3,2-a]pyrimidine-8-ium-7-oleate; (3R)-3-(2-chlorothiazol-5-yl)-6-(3,5-dichlorophenyl)-8-methyl-5-oxo-2,3-dihydrothiazolo[3,2-a]pyrimidine-8-ium-7-oleate, (3R)-3-(2-chlorothiazol-5-yl)-8-ethyl-5-oxo-6-phenyl-2,3-dihydrothiazolo[3,2-a]pyrimidine-8-ium-7-oleate.

[0312] O.5 Nicotinic acetylcholine receptor allosteric activators: spinosad, spinetram.

[0313] O.6 Chloride channel activators: abamectin, emamectin benzoate, ivermectin, lepimectin, milbemectin.

[0314] O.7 Juvenile hormone mimetic agents: hydroprene, quinoprene, methoprene; phenoxycarb, pyriproxyfen.

[0315] O.8 Other nonspecific (multisite) inhibitors: methyl bromide and other alkyl halides; chloropicrin, sulfuryl fluoride, borax, tartaric acid.

[0316] O.9 String organ TRPV channel modulators: Pymetrozine, Pyrifluquinazone.

[0317] O.10 Mite growth inhibitors: clofentezine, hexythiazox, diflovidazine; etoxazole.

[0318] O.11 Microorganisms that destroy the midgut membrane of insects: Bacillus thuringiensis, Bacillus sphaericus and the insecticidal proteins they produce: Bacillus thuringiensis subsp. Israelensis, Bacillus sphaericus, Bacillus thuringiensis subsp. aizawai, Bacillus thuringiensis subsp. Kurstaki, Bacillus thuringiensis subsp. tenebryonis (subsp. Tenebrionis), Bt crop Protein: Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34 / 35Ab1.

[0319] O.12 Mitochondrial ATP synthase inhibitors: diafenthiurone; azocyclotin, cyhexatine, fenbutatine oxide, propargit, tetradiphon.

[0320] O.13 Uncouplers of oxidative phosphorylation via disruption of the proton gradient: chlorfenapyr, DNOC, sulfuramide.

[0321] O.14 Nicotinic acetylcholine receptor (nAChR) channel blockers: bensultap, cartap hydrochloride, thiocyclam, thiosultap sodium.

[0322] O.15 Chitin biosynthesis type O inhibitors: Bistriflurone, Chlorfluazurone, Diflubenzuron, Flucycloxurone, Flufenoxurone, Hexaflumurone, Lufenuron, Novalon, Noviflumurone, Teflubenzuron, Triflumurone.

[0323] O.16 Chitin biosynthesis type 1 inhibitor: Buprofezin.

[0324] O.17 Molting inhibitor: Silomazine.

[0325] O.18 Ecdysone receptor agonists: Methoxyfenozide, tebufenozide, halofenozide, fenozide, chromafenozide.

[0326] O.19 Octopamine receptor agonist: Amitraz.

[0327] O.20 Mitochondrial complex III electron transport inhibitors: hydramethylnon, acequinosyl, fluacrylipylim, bifenazate.

[0328] O.21 Mitochondrial complex I electron transport inhibitors: phenazaquine, fenpyroximate, pyrimidifene, pyridaben, tebufenpyrad, tolfenpyrad, rotenone.

[0329] 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]-hydrazinecarboxamide.

[0330] O.23 Acetyl-CoA carboxylase inhibitors: spirodiclofen, spiromesifen, spirotetramat, spiropidione.

[0331] O.24 Mitochondrial complex IV electron transport inhibitors: aluminum phosphide, calcium phosphide, phosphine, zinc phosphide, cyanide.

[0332] O.25 Mitochondrial complex II electron transport inhibitors: cyenopyrafen, cyflumetofen.

[0333] O.26 Lyanodine receptor modulators: flubendiamide, chlorantraniliprole, cyantraniliprole, cyclaniliprole, tetraniliprole; (R)-3-chloro-N 1 -{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N 2 -(1-methyl-2-methylsulfonylethyl)furalamide, (S)-3-chloro-N 1 -{2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl}-N 2-(1-methyl-2-methylsulfonylethyl)furalamide, 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-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[4-chloro -2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[4-chloro-2-[(di-2-propyl-lambda-4-sulfanylidene)carbamoyl]-6-methyl-phenyl]-2-(3-chloro-2-pyridyl)-5-(trifluoromethyl)pyrazole-3-carboxamide; N-[4,6-dichloro-2-[(di-2-propyl-lambda-4-sulfanylidene N-[4,6-dibromo-2-[(diethyl-lambda-4-sulfanylidene)carbamoyl]-phenyl]-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)-1 H-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; tetrachloranthraniloprole; N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide; cyhalodiamide.

[0334] O.27: Chord organ modulator - Target site undefined: flonicamide.

[0335] O.28. Insecticidal compounds with unknown or uncertain mechanisms of action: Afidopyropen, Ahoxolaner, Azadirachtin, Amidoflumet, Benzoximate, Brofuranilide, Bromopropylate, Quinomethionato, Cryolite, Dichloromethothiaz, Dicofor, Fluphenerim, Flomethoquin, Fluensulfone, Fluhexaphon, Fluopyram, Flularaner, Methoxadiazone, Piperonylbutoxide, Piflubumi, Pyridaryl, Thioxazafen, 11-(4-chloro-2,6-dimethylphenyl) -12-hydroxy-1,4-dioxa-9-azadispiro[4.2.4.2]-tetradec-11-en-10-one, 3-(4'-fluoro-2,4-dimethylbiphenyl-3-yl)-4-hydroxy-8-oxa-1-azadispiro[4.5]dec-3-en-2-one, 1-[2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl]-3-(trifluoromethyl)-1H-1,2,4-triazole-5-amine, Bacillus films firmus)I-1582; ​​Flupyrimine; Fluazaindridine; 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isoxazole-3-yl]-2-methyl-N-(1-oxothietan-3-yl)benzamide; Fluxamethamide; 5-[3-[2,6-dichloro-4-(3,3-dichloroallyloxy)phenoxy]propoxy]-1H-pyrazole; 4-cyano-N-[2-cyano-5-[[2,6-dibromo-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)pro Pyr]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; 4-cyano-3-[(4-cyano-2-methyl-benzoyl)amino]-N-[2,6-dichloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]-2-fluoro-benzamide; N-[5-[[2-chloro-6-cyano-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide;N-[5-[[2-bromo-6-chloro-4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; N-[5-[[2-bromo-6-chloro-4-[1,2,2,3,3,3-hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]-2-cyano-phenyl]-4-cyano-2-methyl-benzamide; 4-cyano-N-[2-cyano-5-[[2,6-dichloro-4-[1,2,2,3,3, 3-Hexafluoro-1-(trifluoromethyl)propyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; 4-Cyano-N-[2-Cyano-5-[[2,6-Dichloro-4-[1,2,2,2-Tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]phenyl]-2-methyl-benzamide; N-[5-[[2-Bromo-6-chloro-4-[1,2,2,2-Tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]carbamoyl]-2-Cyano-phenyl]-4-Cyano-2-methyl-benzamide Mido; 2-(1,3-dioxan-2-yl)-6-[2-(3-pyridinyl)-5-thiazolyl]-pyridin; 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]pyridin-2-carboxamide; N-methylsulfonyl-6-[2-(3-pyridyl)thiazolyl-5-yl]pyridin-2-carboxamide; 1-[(6-clo [L-3-pyridinyl)methyl]-1,2,3,5,6,7-hexahydro-5-methoxy-7-methyl-8-nitroimidazo[1,2-a]pyridine; 1-[(6-chloropyridine-3-yl)methyl]-7-methyl-8-nitro-1,2,3,5,6,7-hexahydroimidazo[1,2-a]pyridine-5-ol; 1-isopropyl-N,5-dimethyl-N-pyridazin-4-ylpyrazole-4-carboxamide; 1-(1,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-ylpyrazole-4-carboxamide;N,5-dimethyl-N-pyridazin-4-yl-1-(2,2,2-trifluoro-1-methyl-ethyl)pyrazole-4-carboxamide; 1-[1-(1-cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazin-4-ylpyrazole-4-carboxamide; N-ethyl-1-(2-fluoro-1-methyl-propyl)-5-methyl-N-pyridazin-4-ylpyrazole-4-carboxamide; 1-(1,2-dimethylpropyl)-N,5-dimethyl-N-pyridazin-4-ylpyrazole Lu-4-carboxamide; 1-[1-(1-cyanocyclopropyl)ethyl]-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; N-methyl-1-(2-fluoro-1-methyl-propyl]-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; 1-(4,4-difluorocyclohexyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; 1-(4,4-difluorocyclohexyl)-N,5-dimethyl-N-pyridazin N-4-ylpyrazole-4-carboxamide, N-(1-methylethyl)-2-(3-pyridinyl)-2H-imidazole-4-carboxamide; N-cyclopropyl-2-(3-pyridinyl)-2H-imidazole-4-carboxamide; N-cyclohexyl-2-(3-pyridinyl)-2H-imidazole-4-carboxamide; 2-(3-pyridinyl)-N-(2,2,2-trifluoroethyl)-2H-imidazole-4-carboxamide; 2-(3-pyridinyl)-N-[(tetrahydro-2-furanyl) N-[(2,2-difluorocyclopropyl)methyl]-2H-imidazole-5-carboxamide; Methyl-2-[[2-(3-pyridinyl)-2H-indazole-5-yl]carbonyl]hydrazine carboxylate; N-[(2,2-difluorocyclopropyl)methyl]-2-(3-pyridinyl)-2H-imidazole-5-carboxamide; N-(2,2-difluoropropyl)-2-(3-pyridinyl)-2H-imidazole-5-carboxamide; 2-(3-pyridinyl-)-N-(2-pyrimidinylmethyl)-2H-imidazole-5-carboxamide;N-[(5-methyl-2-pyradinyl)methyl]-2-(3-pyridinyl)-2H-imidazole-5-carboxamide, ticlopyrazoflor; saloranar, rotilana, 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-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-[3-ethylsulfonyl-5-(trifluoromethyl)- 2-Pyridyl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, isocycloceram, 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; Acinonapyr; Benzpyrimoxane; Tigolana;Chloro-N-(1-cyanocyclopropyl)-5-[1-[2-methyl-5-(1,1,2,2,2-pentafluoroethyl)-4-(trifluoromethyl)pyrazole-3-yl]pyrazole-4-yl]benzamide, 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,5 [S,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-triazol-3-yl]phenyl]carbamate, (2Z)-3-(2-isopropylphenyl)-2-[(E)-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1,2,4-triazol-3-yl]phenyl]methylenehydrazone]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-[3-ethylsulfonyl-6-(trifluoromethyl)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-iodoimidazo[1,2-a]pyridine-2-yl)-3-methyl-6-(tri Fluoromethyl)imidazo[4,5-b]pyridine, 3-ethylsulfonyl-6-iodo-2-[3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridin-2-yl]imidazo[1,2-a]pyridin-8-carbonitride, 2-[3-ethylsulfonyl-8-fluoro-6-(trifluoromethyl)imidazo[1,2-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)imidazo[4,5-b]pyridine, 2-[3-ethylsulfonyl-7-(trifluoro (Methyl)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.

[0336] The active substances referred to as component 2, their preparations, and their activities, such as their activity against harmful fungi, are publicly known (see http: / / www.alanwood.net / pesticides / ); these substances are commercially available. The compounds described in IUPAC nomenclature, their preparations, and their pesticidal activity are also 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 a CAS registry number separated into three parts by a hyphen: the first part consists of two to seven digits, the second part consists of two digits, and the third part consists of one digit.

[0337] According to the present invention, the solid substance (dried substance) of a biocide (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 in biological extracts such as Quillay extract are based on the total weight of the dry content (solid substance) of each extract.

[0338] 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 10 The total weight of each active ingredient can be determined using the amount of CFU of each microorganism, by which the formula states 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 nematodes (juveniles).

[0339] 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, typically 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, typically 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, typically 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.

[0340] 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 in a ratio of 20:1 to 1:20 relative to component 1) if necessary. These ratios are also suitable for mixtures applied by seed treatment.

[0341] When using a mixture containing microbial pesticides for crop protection, the application rate is 1 × 10 6 ~5×10 16 (Above) CFU / ha, preferably 1 × 10 8 ~1 × 10 13 CFU / ha, more preferably 1 × 10 9 ~5×10 15 CFU / ha, especially 1 × 10⁻⁶ 12 ~5×10 14 The range is CFU / ha. For nematodes (e.g., Steinernema feltiae) as a microbial pesticide, the application rate is typically 1 × 10⁻¹⁶ per hectare. 5 ~1 × 10 12 (The above), preferably 1 × 10 8 ~1 × 10 11 , comfortable 5×10 8 ~1 × 10 10 This range includes individuals (for example, eggs, larval eggs, or other living stages, preferably the morphology of immature larval eggs).

[0342] When using a mixture containing microbial pesticides for seed treatment, the application rate is generally 1 × 10⁻⁶. 6 ~1 × 10 12 (Above) CFU / seed, preferably 1 × 10 6 ~1 × 10 9The range is CFU / seed. Furthermore, the application rate for seed treatment is generally 1 × 10⁶ per 100 kg of seed. 7 ~1 × 10 14 (Above) CFU, preferably 1 × 10 per 100 kg of seeds 9 ~1 × 10 12 This falls under the scope of CFU.

[0343] 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.

[0344] 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).

[0345] 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.

[0346] As component 2), a mixture containing at least one active substance selected from other respiratory inhibitors of group A), more preferably compounds (A.4.5) and (A.4.11), and particularly (A.4.11), is also preferred.

[0347] 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.

[0348] A mixture containing, as component 2), more preferably compounds (B.2.4), (B.2.5), (B.2.6), and (B.2.8) selected from delta-14-reductase inhibitors of group B), is also preferred; in particular, a mixture containing at least one active substance selected from (B.2.4) is also preferred.

[0349] Component 2) is selected from phenylamide and acyl amino acid bactericides of group C), more preferably from compounds (C.1.1), (C.1.2), (C.1.4), and (C.1.5); a mixture containing at least one active substance selected particularly from (C.1.1) and (C.1.4) is also preferred.

[0350] 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.

[0351] Component 2) is selected from group D), more preferably from compounds (D.1.1), (D.1.2), (D.1.5), (D.2.4), and (D.2.6); a mixture containing at least one active substance selected from (D.1.2), (D.1.5), and (D.2.6) is also preferred.

[0352] A mixture containing at least one active substance selected from group E) as component 2 is also preferred, more preferably compounds (E.1.1), (E.1.3), (E.2.2), and (E.2.3); in particular (E.1.3).

[0353] 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 as component 2).

[0354] Component 2) is 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.

[0355] As component 2), a compound selected from group H) is more preferably selected from compounds (H.2.2), (H.2.3), (H.2.5), (H.2.7), (H.2.8), (H.3.2), (H.3.4), (H.3.5), (H.4.9), and (H.4.10); a mixture containing at least one active substance selected from (H.2.2), (H.2.5), (H.3.2), (H.4.9), and (H.4.10) is also preferred.

[0356] 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).

[0357] Component 2) is 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 at least one active substance selected from (J.1.5) is also preferred.

[0358] As component 2), a compound selected from group K) is more preferably selected from compounds (K.1.41), (K.1.42), (K.1.44), (K.1.47), (K.1.57), (K.1.58), and (K.1.59); a mixture containing at least one active substance selected from (K.1.41), (K.1.44), (K.1.47), (K.1.57), (K.1.58), and (K.1.59) is also preferred.

[0359] Bio-pesticides of group L1) and / or group L2) may also have insecticidal activity, acaricidal activity, molluscicidal activity, pheromoneicidal activity, nematicidal activity, plant stress reduction activity, plant growth regulator activity, plant growth promotion activity and / or yield-increasing activity. Bio-pesticides of group L3) and / or group L4) may also have fungicidal activity, bactericidal activity, virucidal activity, plant defense activation activity, plant stress reduction activity, plant growth regulator activity, plant growth promotion activity and / or yield-increasing activity. Bio-pesticides of group L5) may also have bactericidal activity, bactericidal activity, virucidal activity, plant defense activation activity, insecticidal activity, acaricidal activity, molluscicidal activity, pheromoneicidal activity and / or nematicidal activity.

[0360] 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, suspensions in whole broth cultures, and metabolite-containing culture media or purified metabolites obtained from whole broth cultures of microorganisms.

[0361] Many of these biocides are deposited under the deposit numbers mentioned herein (prefixes such as ATCC or DSM refer to acronyms of each culture collection; see, for example, http: / / www.wfcc.info / ccinfo / collection / by_acronym / for details), 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® (Gramineas), A. brasilense strains Ab-V5 and Ab-V6 (e.g., Novozymes BioAg Produtos papra Agricultura Ltda., Quattro Barras, Brazil, AzoMax or Simbiose-Agro, Brazil, Simbiose-Maiz®; 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 species plantarum (spp. plantarum) strain (formerly sometimes called B. subtilis). Currently, it is 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 of 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 of AbiTEP GmbH, Germany), isolated from soil in Brandenburg, 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) of Bayer Crop Science LP, USA, Bassp. plantarum or B. velezensis QST-713 (NRRL B-21661; e.g., Serenade (registered trademark) MAX of Bayer Crop Science LP, USA), isolated from a peach orchard in California, USA in 1995, and Bassp. plantarum or B. velezensis isolated in South Dakoda, USA in 1992.B. velezensis TJ1000 (also known as 1BE; ATCC BAA-390; Canadian Patent Application Publication No. 2471555A1; e.g., QuickRoots® by TJ Technologies, Watertown, SD, USA), B. firmus CNCM I-1582 (a mutant of the 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® by Bayer CropScience LP, USA), B. pumilus GHA 25 (IDAC 260707-01; e.g., Premier PRO-MIX® (registered trademark) BX) of 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 invaded by 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 2808 was isolated in 1998 from soil collected in Pohnpei, Federated States of Micronesia (NRRL B-30087; e.g., Sonata® or Ballad® Plus by Bayer Crop Science LP, USA), B. simplex ABU 288 (NRRL B-50304; U.S. Patent No. 8,445,255), and B. simplex was isolated from red beet roots in North America.B. subtilis FB17 (also known as UD 1022 or UD 10-22) (ATCC PTA-11857; System.Appl.Microbiol.27,372-379,2004; US Patent Application Publication No. 2010 / 0260735; International Publication No. 2011 / 109395); B. thuringiensis ssp. aizawai ABTS-1857 (also known as ABG-6346; ATCC SD-1372); for example, BioFa HD-1, isolated in 1967 from black larvae of the cottonweed moth (XenTari®, AG, Muensingen, Germany) and Brownsville, Texas, USA, is the same as Bt subspecies kurstaki (Btssp. kurstaki) ABTS-351 (ATCC SD-1275; e.g., Dipel® DF, Valent BioSciences, IL, USA), and Bt subspecies kurstaki (Btssp. kurstaki) SB4 (NRRL B-50753; e.g., Beta, 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) of Valent BioSciences, Switzerland), Beauveria bassiana GHA (ATCC 74250; e.g., BotaniGard(registered trademark) 22WGP of Laverlam Int. Corp., USA), B. bassiana JW-1 (ATCC 74040; e.g., CBC(Europe)SrlNaturalis (registered trademark) of Italy, B. bassiana PPRI 5339 (NRRL 50757; e.g., BroadBand (registered trademark) from BASF Agricultural Specialties (Pty) Ltd., South Africa), isolated from the larvae of the tortoise beetle Conchyloctenia punctata, Bradyrhizobium elkanii strain SEMIA 5019 (also known as 29W) isolated in Rio de Janeiro, Brazil, and SEMIA 587 (Appl. Environ. Microbiol. 73(8), 2635, 2007; e.g., BASF Agricultural Specialties), isolated in 1967 in Rio Grande do Sul from an area previously inoculated with North American isolates and used in commercially available inoculations since 1968. GELFIX Ltd., Brazil 5), B. japonicum 532c (Nitragin 61A152; Can. J. Plant. Sci. 70, 661-666, 1990; e.g., in Rhizoflo®, Histic®, Hicoat® Super of BASF Agricultural Specialties Ltd., Canada), isolated from a field in Wisconsin, USA, and one of 138 USDA strains of the 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 by Appl. Environ. Microbiol. 73(8),2635,2007, the B. japonicum strain: Embrapa-Cerrados was isolated from soil in the Cerrados region of Brazil and has been used in commercially available inoculum since 1992. SEMIA 5079 (CPAC 15; e.g., BASF Agricultural Specialties Ltd.)(GELFIX 5 or ADHERE 60 from Brazil), obtained under laboratory conditions by Embrapa-Cerrados in Brazil, has been used in commercially available inoculum since 1992, and is a natural mutant of SEMIA 586 (CB259) originally isolated in the USA. B. japonicum SEMIA 5080 (CPAC7; e.g., GELFIX 5 or ADHERE 60 of 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 of Bayer CropScience AG, Germany); Harpin (alpha-beta) protein (Science 257,85-88,1992; e.g., Messenger (trademark) or HARP-N Tek of Plant Health Care plc, UK), Helicoverpa armigera nuclear polyhedron virus (HearNPV) (J. Invertebrate Pathol. 107,112-126,2011; e.g., Helicovex (registered trademark) of Adermatt Biocontrol, Switzerland; Diplomata (registered trademark) of Koppert, Brazil; Vivus (registered trademark) Max of AgBiTech Pty Ltd., Queensland, Australia), Helicoverpa zea single capsid nuclear polyhedron virus (HzSNPV) (e.g., Gemstar (registered trademark) of Certis LLC, USA), Helicoverpa zea nuclear polyhedron virus ABA-NPV-U (e.g., AgBiTech Pty Ltd.Heligen (registered trademark) of Queensland, Australia; Heterorhabditis bacteriophora (e.g., Nemasys (registered trademark) G of 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) of Certis LLC, USA) isolated from mealybugs on gynura in Apopka, Florida, USA; Metarhizium anisopliae var. anisopliae isolated from Codlinga in Austria.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 (US Patent No. 6,994,849; NRRL Y-30752; e.g., formerly Agrogreen, Shemer® 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 Paenibacillus alvei NAS6G6 (International Publication No. 2014 / 029697; NRRL B-50755; e.g., BAC-UP from BASF Agricultural Specialties (Pty) Ltd., South Africa), isolated from the rhizosphere of pasture grass in South Africa at least before 2008; Paenibacillus strain P. epiphyticus Lu17015 (International Publication No. 2016 / 020371; DSM 26971), and 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 of 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 Specialities Limited, UK), S. feltiae (e.g., BioWorks, Inc.)Nemashield® (registered trademark) of the USA; Nemasys® (registered trademark) of 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® 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) of Plantshield Inc., USA, or SabrEx® (trademark) of Advanced Biological Marketing Inc., Van Wert, OH, USA.

[0362] According to another embodiment of the mixture, at least one pesticide II is selected from the group L1) to L5): L1) Microbial pesticides having fungicidal, bactericidal, virucidal activity and / or plant defense activator 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 25 (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), P. 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 activity and / or plant defense activator activity: Harbin 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), (Quillay 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).

[0363] 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 the above-mentioned group L), particularly at least one bio-pesticide selected from group L1) and group L2), and optionally at least one suitable auxiliary agent.

[0364] 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 the above-mentioned group L), particularly at least one bio-pesticide selected from groups L3) and L4), and optionally at least one suitable auxiliary agent.

[0365] 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. 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 treating reproductive materials, i.e., seed treatment purposes, and are also suitable for soil treatment. These seed treatment mixtures are particularly suitable for crops such as cereals, maize, and legumes such as soybeans.

[0366] 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. 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 above strains 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, cereals, corn, and leguminous crops such as soybeans.

[0367] A composition containing a mixture of active ingredients can be prepared by conventional means, for example, by the means given for the composition of compound I.

[0368] When viable 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]

[0369] I. Synthesis Examples: Step 1-2: Preparation of trimethylchroman-4-one oxime Hydroxylamine hydrochloride (72.87 g, 3 eq) was added to a solution of 2,2,3-trimethylchroman-4-one (1 eq, 66.5 g) in pyridine (423 ml, 15 eq), and the reaction mixture was stirred at 85°C for 18 hours. The reaction solution was poured into water (1000 ml), extracted with heptane, and washed sequentially with water and saline solution, and dried on anhydrous magnesium sulfate. Upon removal of the solvent under reduced pressure, the title compound (66.6) was obtained as a brown powder. The title compound was used without further purification. 1 H NMR(400MHz,CDCl3):μ[ppm]:9.15(s,1H),7.75(dd,J=7.9,1.7Hz,1H),7.26(dd,J=7.1,1.5Hz,1H),6.91(ddd,J=8.2 ,7.2,1.2Hz,1H),6.86(dd,J=8.3,1.2Hz,1H),3.39(q,J=7.0Hz,1H),1.45(s,3H),1.27(s,3H),1.13(d,J=7.0Hz,3H).

[0370] Step 2 - Preparation of 2,2,3-trimethyl-3,4-dihydro-1,4-benzoxazepine-5-one 2,2,3-Trimethylchroman-4-one oxime (66 g, 1 eq) was added to thionyl chloride (80 g, 3.5 eq) at a temperature below 30°C, and the reaction mixture was stirred at 50°C for 17 hours. After removing thionyl chloride under reduced pressure, the residue was poured into 1,4-dioxane (500 ml) and water (200 ml) and stirred at 80°C for 1 hour. After removing 1,4-dioxane under reduced pressure, the resulting residue was extracted with ethyl acetate, washed sequentially with water and saline solution, and dried on anhydrous magnesium sulfate. After removing the solvent under reduced pressure, the crude product was purified by flash chromatography on silica gel using heptane / MTBE as the eluent to obtain the title compound (25.4 g) as a powder. 1H NMR(400MHz,CDCl3):μ[ppm]:7.74(dd,J=7.7,1.8Hz,1H),7.44(td,J=7.7,1.8Hz,1H),7.20(td,J=7.5,1.1Hz,1H),6 .98(dd,J=8.1,1.1Hz,1H),6.44(s,1H),3.37(qd,J=6.9,5.2Hz,1H),1.39(s,3H),1.29(s,3H),1.20(d,J=6.9Hz,3H).

[0371] Step 3-5 Preparation of chloro-2,2,3-trimethyl-3H-1,4-benzoxazepine A mixture of 2,2,3-trimethyl-3,4-dihydro-1,4-benzoxazepine-5-one (10 g, 1 eq), phosphoryl chloride (100 ml), and phosphorus(V) chloride (11.67 g, 1.15 eq) was heated and stirred at 110°C for 2 hours. After cooling, the reaction mixture was concentrated under reduced pressure, diluted with dichloromethane, washed twice with saturated sodium carbonate solution, and dried on anhydrous magnesium sulfate. The crude product (10.8 g) was obtained by removing the solvent under reduced pressure. The title compound was used without further purification.

[0372] Steps 4-5 - Preparation of [6-(difluoromethoxy)-5-methyl-3-pyridyl]-2,2,3-trimethyl-3H-1,4-benzoxazepine [6-(difluoromethyl)-5-methyl-3-pyridyl]boronic acid (3.11 g, 1.2 eq), potassium carbonate (3.83 g, 2 eq), silver oxide (1.61 g, 0.5 eq), and dichlorobis(triphenylphosphine)palladium(II) (490 mg, 0.05 eq) were added to a solution of 5-chloro-2,2,3-trimethyl-3H-1,4-benzoxazepine (3.1 g, 1 eq) in dry tetrahydrofuran (57 mL), and the mixture was stirred at 80°C for 18 hours under an argon atmosphere. After cooling, the reaction solution was diluted with ethyl acetate, washed sequentially with water and saline solution, dried on anhydrous magnesium sulfate, and concentrated under reduced pressure. The crude product was purified by high-performance liquid chromatography on silica RP-18 using acetonitrile / water as the eluent to obtain the title compound (1.5 g) as a white powder. 1 H NMR (400MHz, CDCl3): μ[ppm]:8.58(d,J=1.9Hz,1H),7.92(s,1H),7.46(t,J=7.7Hz,1H),7.18(td,J=7.5,1.2Hz,1H),7.0(td,J =7.7,1.4Hz,2H),6.73(t,J=54.5Hz,1H),3.28(d,J=6.8Hz,1H),2.54(d,J=2.2Hz,3H),1.59(s,3H),1.45(s,3H),1.39(s,3H).

[0373] Table 18

[0374] Table 19

[0375] Table 20

[0376] Table 21

[0377] Table 22

[0378] Table 23

[0379] Table 24

[0380] Table 25

[0381] [Table 26]

[0382] [Table 27]

[0383] [Table 28]

[0384] [Table 29]

[0385] [Table 30]

[0386] [Table 31]

[0387] [Table 32]

[0388] [Table 33]

[0389] Microtest The active compound was separately formulated as a stock solution with a concentration of 10,000 ppm in dimethyl sulfoxide.

[0390] 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 indicated concentration. A spore suspension in aqueous biomalt or yeast-bactopeptone-sodium acetate solution of Botorci cinerea was added. The plates were placed in a steam-saturated chamber at 18°C. MTP was measured at a wavelength of 405 nm 7 days after inoculation using a spectrophotometer.

[0391] In this test, samples treated with 31 ppm of the active substance from Examples Ex-1, Ex-2, Ex-3, Ex-4, Ex-8, Ex-9, Ex-10, and Ex-11 each showed 0% pathogen growth.

[0392] Example 2 - Activity against Fusarium culmorum in microtiter plate testing The stock solutions were mixed according to the specified ratio, pipetted onto microtiter plates (MTPs), and diluted with water to the indicated concentrations. Aqueous biomalt or spore suspension of Fusarium culmorum in yeast-bactopeptone-glycerin or DOB solution was added. The plates were placed in a steam-saturated chamber at 18°C. MTP was measured at a wavelength of 405 nm 7 days after inoculation using a spectrophotometer.

[0393] In this test, samples treated with 31 ppm of the active substance from Examples Ex-2 and Ex-3 showed a 1% increase in pathogen growth.

[0394] Example 3 - Activity of Venturia inaequalis in microtiter plate tests 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 according to the specified ratio, pipetted onto a microtiter plate (MTP), and diluted with water to obtain the indicated concentration. A spore suspension of Botorci cinerea in aqueous biomalt or yeast-bactopeptone-sodium acetate solution was added.

[0395] In this test, samples treated with 31 ppm of the active substance from Examples Ex-1, Ex-4, Ex-12 (50 ppm), Ex-18, Ex-21, Ex-22, Ex-24, Ex-28, Ex-29, Ex-31, Ex-36, Ex-44, Ex-45, and Ex-47 showed a pathogen growth of up to 20%.

[0396] Example 4 - Activity against Botrytis cinerea, a gray mold fungus, 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 according to the specified ratio, pipetted onto a microtiter plate (MTP), and diluted with water to obtain the indicated concentration. A spore suspension of Botorci cinerea in aqueous biomalt or yeast-bactopeptone-sodium acetate solution was added.

[0397] In this test, samples treated with 31 ppm of the active substance from Examples Ex-1, Ex-3, Ex-4, Ex-6, Ex-7, Ex-8, Ex-9, Ex-11, Ex-12, Ex-13, Ex-15, Ex-16, Ex-17, Ex-19, Ex-20, Ex-21, Ex-22, Ex-25, Ex-26, Ex-27, Ex-28, Ex-29, Ex-30, Ex-31, Ex-32, Ex-33, Ex-34, Ex-36, Ex-38, Ex-39, Ex-43, Ex-45, Ex-46, Ex-47, Ex-48, Ex-49, Ex-50, Ex-51, and the racemic mixture Ex-52+Ex-52, Ex-68, and Ex-69 showed pathogen growth of up to 1%.

[0398] Example 5 - Activity against Fusarium culmorum in microtiter plate testing 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 according to the specified ratio, pipetted onto a microtiter plate (MTP), and diluted with water to obtain the indicated concentration. A spore suspension of Fusarium culmorum in aqueous biomalt yeast-bactopeptone-glycerin or DOB solution was added.

[0399] In this test, samples treated with 31 ppm of the active substance from Examples Ex-3, Ex-11, Ex-26, Ex-27, Ex-30, Ex-34, Ex-46, Ex-48, Ex-49, and Ex-52 and Ex-53 as racemic mixtures showed pathogen growth of up to 9%.

[0400] Example 6 - Activity of Septoria tritici against wheat leaf blight 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 according to the specified ratio, pipetted onto a microtiter plate (MTP), and diluted with water to the indicated concentration. Aqueous biomalt or yeast-bactopeptone-glycerin or DOB solution of Septoria tritici spore suspension was added.

[0401] In this test, samples treated with 31 ppm of the active substance from Examples Ex-21, Ex-28, Ex-33, Ex-47, and Ex-48 showed a reduction in pathogen growth to 18%.

[0402] Example 7 - Activity against Microdochium nivale in microtiter plate testing 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 according to the specified ratio, pipetted onto a microtiter plate (MTP), and diluted with water to the indicated concentration. Subsequently, a spore suspension of Microdochium nivale isolate in DOB medium (pH 7) was added.

[0403] In this test, samples treated with 31 ppm of the active substance from Examples Ex-1, Ex-2, Ex-3, Ex-4, Ex-6, Ex-7, Ex-9, Ex-11, Ex-12, Ex-13, Ex-15, Ex-16, Ex-19, Ex-20, Ex-21, Ex-22, Ex-23, Ex-24, Ex-25, Ex-26, Ex-27, Ex-28, Ex-29, Ex-30, Ex-31, Ex-32, Ex-33, Ex-34, Ex-36, Ex-37, Ex-38, Ex-39, Ex-41, Ex-44, Ex-45, Ex-46, Ex-47, and the racemic mixtures Ex-52 and Ex-53, Ex-68, and Ex-69 each showed a pathogen growth of up to 19%.

[0404] Example 8 - Activity against Colletotrichum orbiculare in microtiter plate testing 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 according to the specified ratio, pipetted onto a microtiter plate (MTP), and diluted with water to the indicated concentration. Subsequently, a spore suspension of anthrax-causing fungus (Colletotrichum orbiculare) isolate in DOB medium (pH 7) was added.

[0405] In this test, samples treated with 31 ppm of the active substance from Examples Ex-1, Ex-2, Ex-3, Ex-4, Ex-7, Ex-9, Ex-11, Ex-12, Ex-13, Ex-16, Ex-19, Ex-22, Ex-24, Ex-25, Ex-26, Ex-27, Ex-28, Ex-29, Ex-32, Ex-33, Ex-34, Ex-36, Ex-41, Ex-45, Ex-52 and Ex-53 as racemic mixtures, and Ex-69, each showed a pathogen growth of up to 15%.

[0406] Example 9 - Activity against Leptosphaeria nodorum 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 according to the specified ratio, pipetted onto a microtiter plate (MTP), and diluted with water to the indicated concentration. Subsequently, a spore suspension of Leptosphaeria nodorum isolates in DOB medium (pH 7) was added.

[0407] In this test, Examples Ex-1, Ex-2, Ex-3, Ex-4, Ex-6, Ex-7, Ex-9, Ex-11, Ex-12, Ex-13, Ex-15, Ex-16, Ex-17, Ex-18, Ex-19, Ex-20, Ex-21, Ex-22, Ex-23, Ex-24, Ex-25, Ex-26, Ex-27, Ex-28, Ex-29, Ex-30, Ex-31, Samples treated with 31 ppm of the active substance from Ex-32, Ex-33, Ex-34, Ex-36, Ex-37, Ex-38, Ex-39, Ex-40, Ex-42, Ex-43, Ex-44, Ex-45, Ex-46, Ex-47, and Ex-52 and Ex-53 as racemic mixtures, Ex-68, and Ex-69, each showed pathogen growth of up to 12%.

[0408] Example 10 - Activity of Fusarium gramminearis in microtiter plate testing 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 according to the specified ratio, pipetted onto a microtiter plate (MTP), and diluted with water to the indicated concentration. Subsequently, a spore suspension of Fusarium gramminearis isolate in DOB medium (pH 7) was added.

[0409] In this test, samples treated with 31 ppm of the active substance from Examples Ex-2, Ex-27, Ex-30, and Ex-34 showed a reduction in pathogen growth to 16%.

[0410] Example 11 - Activity of Monilinia laxa in microtiter plate testing 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 according to the specified ratio, pipetted into a microtiter plate (MTP), and diluted with water to the indicated concentration. Subsequently, a spore suspension of Monilinia laxa isolate in DOB medium (pH 7) was added.

[0411] In this test, samples treated with 31 ppm of the active substance from Examples Ex-1, Ex-2, Ex-3, Ex-4, Ex-6, Ex-7, Ex-9, Ex-10, Ex-11, Ex-12, Ex-13, Ex-15, Ex-16, Ex-17, Ex-18, Ex-20, Ex-21, Ex-22, Ex-23, Ex-24, Ex-25, Ex-26, Ex-27, Ex-28, Ex-29, Ex-30, Ex-31, Ex-32, Ex-33, Ex-34, Ex-36, Ex-40, Ex-44, Ex-45, Ex-47, and the racemic mixtures Ex-52 and Ex-53, Ex-68, and Ex-69 each showed a pathogen growth of up to 20%.

[0412] Example 12 - Activity of Ustilago maydis in microtiter plate testing 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 according to the specified ratio, pipetted into a microtiter plate (MTP), and diluted with water to the indicated concentration. Subsequently, a spore suspension of Ustilago maydis isolate in DOB medium (pH 7) was added.

[0413] In this test, samples treated with 31 ppm of the active substance from Examples Ex-1, Ex-24, and Ex-41 showed 0% pathogen growth in each case.

[0414] Example 13 - Activity against Pyrenophora teres Qoi (FL129) resistant isolates in microtiter plate testing 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 according to the specified ratio, pipetted into a microtiter plate (MTP), and diluted with water to the indicated concentration. Subsequently, a spore suspension of a Pyrenophora teres Qoi (FL129) resistant isolate in DOB medium (pH 7) was added.

[0415] In this test, samples treated with 31 ppm of the active substance from Examples Ex-1, Ex-2, Ex-3, Ex-4, Ex-6, Ex-7, Ex-9, Ex-10, Ex-11, Ex-12, Ex-13, Ex-15, Ex-16, Ex-19, Ex-20, Ex-21, Ex-22, Ex-23, Ex-24, Ex-25, Ex-26, Ex-27, Ex-28, Ex-29, Ex-30, Ex-32, Ex-33, Ex-34, Ex-36, Ex-37, Ex-38, Ex-39, Ex-41, Ex-42, Ex-43, Ex-44, Ex-45, Ex-47, and the racemic mixtures Ex-52 and Ex-53, Ex-68, and Ex-69 showed a pathogen growth of up to 19%.

[0416] Example 14 - Activity against Leptosphaeria maculans 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 according to the specified ratio, pipetted into a microtiter plate (MTP), and diluted with water to the indicated concentration. Subsequently, a spore suspension of Leptosphaeria maculans isolate in DOB medium (pH 7) was added.

[0417] In this test, samples treated with 31 ppm of the active substance from Examples Ex-1, Ex-2, Ex-3, Ex-4, Ex-6, Ex-11, Ex-12, Ex-15, Ex-16, Ex-17, Ex-18, Ex-19, Ex-20, Ex-21, Ex-22, Ex-23, Ex-25, Ex-26, Ex-27, Ex-28, Ex-29, Ex-30, Ex-31, Ex-32, Ex-33, Ex-34, Ex-36, Ex-37, Ex-38, Ex-39, Ex-41, Ex-42, Ex-43, Ex-44, Ex-45, Ex-46, Ex-68, and Ex-69 showed a pathogen growth of up to 19% in each case.

[0418] Example 15 - Activity of Phytophthora infestans 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 according to the specified ratio, pipetted into a microtiter plate (MTP), and diluted with water to the indicated concentration. Subsequently, a spore suspension of Pyrenophora infenstans isolate in DOB medium (pH 7) was added.

[0419] In this test, samples treated with 31 ppm of the active substance from Examples Ex-1, Ex-2, Ex-8, Ex-9, Ex-10, Ex-11, Ex-12, Ex-13, Ex-15, Ex-20, Ex-23, Ex-24, and Ex-31 showed a reduction in pathogen growth to 19%.

[0420] Example 16 - Activity against Mycosphorella fijiensis in microtiter plate testing 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 according to the specified ratio, pipetted into a microtiter plate (MTP), and diluted with water to the indicated concentration. Subsequently, a spore suspension of Mycosphorella fijiensis isolate in DOB medium (pH 7) was added.

[0421] In this test, samples treated with 31 ppm of the active substance from Examples Ex-1, Ex-2, Ex-3, Ex-4, Ex-6, Ex-15, Ex-20, Ex-21, Ex-22, Ex-23, Ex-24, Ex-25, Ex-26, Ex-27, Ex-28, Ex-29, Ex-30, Ex-31, Ex-32, Ex-33, Ex-34, Ex-36, Ex-37, Ex-38, Ex-39, Ex-44, and Ex-45 showed a reduction in pathogen growth to 20%.

[0422] Example 17 - Activity of Corynespora cassiicola 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 according to the specified ratio, pipetted onto a microtiter plate (MTP), and diluted with water to the indicated concentration. Subsequently, a spore suspension of Corynespora cassiicola isolate in DOB medium (pH 7) was added.

[0423] In this test, samples treated with 31 ppm of the active substance from Examples Ex-24, Ex-25, Ex-26, Ex-27, Ex-28, Ex-29, Ex-30, Ex-31, Ex-32, Ex-33, Ex-34, Ex-36, Ex-44, Ex-45, Ex-47, and Ex-69 showed a pathogen growth of up to 16% in each case.

[0424] Example 18 - Activity of Corynespora cassiicola (CORYCA-G) G413A mutant in microtiter plate testing 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 according to the specified ratio, pipetted onto a microtiter plate (MTP), and diluted with water to the indicated concentration. Subsequently, a spore suspension of Corynespora cassiicola (CORYCA-G) G413A mutant isolate in DOB medium (pH 7) was added.

[0425] In this test, samples treated with 31 ppm of the active substance from Examples Ex-24, Ex-25, Ex-26, Ex-27, Ex-28, Ex-29, Ex-30, Ex-31, Ex-32, Ex-33, Ex-34, Ex-36, Ex-38, Ex-44, Ex-45, Ex-47, and Ex-69 showed a pathogen growth of up to 18% in each case.

[0426] The measured parameters were compared with the growth of a control variant (100%) that did not contain the active compound and a blank value that did not contain fungi, to determine the relative growth (%) of the pathogen for each active compound.

[0427] 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.

[0428] Next, this stock solution was diluted with the solvent-emulsifier-water mixture described below to obtain the final concentrations shown in the table below.

[0429] Example 19 - Preventive fungicide 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 solutions containing concentrated active ingredients or mixtures listed in the table below until they ran out. The following day, the plants were inoculated with a biomalt aqueous solution or DOB aqueous solution containing a suspension of Botrytis cinerea spores. The plants were then immediately transferred to a humidified chamber. After 5 days under conditions of 22-24°C and saturated relative humidity, the degree of fungal damage to the leaves was visually evaluated as the percentage of diseased leaves.

[0430] In this study, 90% of untreated plants were infected, while samples treated with 250 ppm of the active substance from Examples Ex-1, Ex-2, Ex-3, Ex-4, Ex-8, Ex-9, Ex-12, Ex-13, Ex-16, and Ex-18 showed pathogen growth of up to 15%.

[0431] Example 20 - Preventive fungicidal control of rapeseed white mold disease using Sclerotinia sclerotiorum Rapeseed plants were grown in pots until they reached the 13-14 leaf stage. These plants were sprayed with the aforementioned spray solutions containing concentrates of the active ingredients or mixtures thereof listed in the table below until the solution ran out. The plants were air-dried. The following day, the treated rapeseed petals were fixed to leaves 1 and 2 with 25 μl of 2.5% methylcellulose. 25 μl of Sclerotinia sclerotiorum spore suspension was pipetteed onto each fixed rapeseed petal. After 14 days under conditions of 20°C and 60% relative humidity, the degree of fungal damage to the leaves was visually evaluated as the percentage of diseased leaf area.

[0432] In this study, while untreated plants were 100% infected, samples treated with 100 g / ha of the active substance from Examples Ex-1, Ex-2, Ex-3, Ex-4, Ex-7, Ex-8, Ex-11, Ex-12, Ex-15, Ex-17, Ex-20, Ex-21, Ex-22, Ex-25, Ex-26, Ex-27, Ex-28, Ex-30, Ex-31, Ex-32, Ex-33, Ex-34, Ex-40, Ex-45, and Ex-47 showed a maximum pathogen growth of 15%.

[0433] Example 21 - Preventive fungicide 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 solutions containing concentrated active ingredients or mixtures listed in the table below until they ran out. The following day, the plants were inoculated with a biomalt aqueous solution or DOB aqueous solution containing a suspension of Botrytis cinerea spores. The plants were then immediately transferred to a humidified chamber. After 5 days under conditions of 22-24°C and saturated relative humidity, the degree of fungal damage to the leaves was visually evaluated as the percentage of diseased leaves.

[0434] In this study, 100% of untreated plants were infected, while samples treated with 100 g / ha of the active substance from Examples Ex-8, Ex-12, Ex-25, Ex-26, and Ex-27 showed pathogen growth of up to 18% in each case.

[0435] Example 22 - Long-term 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 solutions containing concentrated active ingredients or mixtures listed in the table below until the solution ran out. The plants were then cultivated in a greenhouse for 7 days and inoculated with biomalt or DOB aqueous solution containing a spore suspension of Botrytis cinerea. The plants were then immediately transferred to a humidified chamber. After 5 days under conditions of 22-24°C and saturated relative humidity, the degree of fungal damage to the leaves was visually evaluated as the percentage of diseased leaves.

[0436] In this study, 90% of untreated plants were infected, while samples treated with 100 g / ha of the active substance from Examples Ex-21, Ex-25, Ex-26, Ex-27, Ex-28, Ex-29, Ex-45, Ex-47, and Ex-69 showed pathogen growth of up to 14% in each case.

[0437] Comparative Example Example 1 - Activity of Septoria tritici against wheat leaf blight 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 according to the specified ratio, pipetted onto a microtiter plate (MTP), and diluted with water to the indicated concentration. Aqueous biomalt or spore suspension of Septoria tritici in yeast-bactopeptone-glycerin or DOB solution was added. The plate was placed in a steam-saturated chamber at 18°C. MTP was measured at a wavelength of 405 nm 7 days after inoculation using a spectrophotometer.

[0438] [Table 34]

[0439] Example 2 - Activity of Leptosphaeria nodorum against wheat leaf spots 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 according to the specified ratio, pipetted onto a microtiter plate (MTP), and diluted with water to the indicated concentration. Aqueous biomalt or spore suspension of Leptosphaeria nodorum in yeast-bactopeptone-glycerin or DOB solution was added. The plate was placed in a steam-saturated chamber at 18°C. MTP was measured at a wavelength of 405 nm 7 days after inoculation using a spectrophotometer.

[0440] [Table 35] Several embodiments are shown below. Item 1 Formula I as a disinfectant [ka] (In the formula, R 1 H is; R 2 In each case, independently, halogen, CN, and C 1 ~C 6 -alkyl, C 1 ~C 6 -Halogen alkyl, C 2 ~C 6 -Alkenil, C 2 ~C 6 -Halogenated alkenyl, C 2 ~C 6 -Alkinyl, OC 1 ~C 6 -alkyl, C 3 ~C 6 - Selected from cycloalkyl groups; R 3 In each case, independently, C 1 ~C 6 -alkyl, C 1 ~C 6 -Halogen alkyl, C 2 ~C 6 -Alkenil, C 2 ~C 6 -Halogenated alkenyl, C 2 ~C 6 -Alkinyl, OC 1 ~C 6 -alkyl, C 3 ~C 6 - Selected from cycloalkyl; R 4 H is; R 5 In each case, independently, H, F, CN, C 1 ~C 6 -alkyl, C 1 ~C 6 -Halogen alkyl, C 2 ~C 6 - Selected from alkenyl, phenyl, and benzyl, The aforementioned portion is either unsubstituted or contains 1 to 3 groups R 5a It is replaced by the 1 to 3 groups R 5a These are, independently of each other, halogen, CN, and C 1 ~C 6 -alkyl, C 1 ~C 6 -Halogenated alkyl, OC 1 ~C 6 -Selected from alkyl groups; R 6 In each case, independently, H, F, CN, C 1 ~C 6 -alkyl, C 1 ~C 6 -Halogen alkyl, C 2 ~C 6 - Selected from alkenyl, phenyl, and benzyl, R 6 The aforementioned portion is either unsubstituted or has 1 to 3 bases R 6a It is replaced by the 1 to 3 groups R 6a These are, independently of each other, halogen, CN, and C 1 ~C 6 -alkyl, C 1 ~C 6 -Halogenated alkyl, OC 1 ~C 6 - Selected from alkyl groups; or R 5 and R 6 They either form an O molecule together with the C atom to which they are bonded; or R 5 and R 6 Together with the C atom to which they are bonded, C 3 ~C 6 -Forms a 3- to 6-membered saturated heterocycle containing 1, 2, or 3 heteroatoms from the group consisting of cycloalkyl or O and S; the cycloalkyl or heterocycle is unsubstituted or contains halogens, C 1 ~C 6 -alkyl, C 1 ~C 6 - May be substituted with halogen alkyl; R 7 In each case, independently, H, F, CN, C 1 ~C 6 -alkyl, C 1 ~C 6 -Halogen alkyl, C 2 ~C 6 - Selected from alkenyl, phenyl, and benzyl, The aforementioned portion is either unsubstituted or contains 1 to 3 groups R 7a It is replaced by the 1 to 3 groups R 7a These are, independently of each other, halogen, CN, and C 1 ~C 6 -alkyl, C 1 ~C 6 -Halogenated alkyl, OC 1 ~C 6 -Selected from alkyl groups; R 8 In each case, independently, H, F, CN, C 1 ~C 6 -alkyl, C 1 ~C 6 -Halogen alkyl, C 2 ~C 6 - Selected from alkenyl, phenyl, and benzyl, The aforementioned portion is either unsubstituted or contains 1 to 3 groups R 8a It is replaced by the 1 to 3 groups R 8a These are, independently of each other, halogen, CN, and C 1 ~C 6 -alkyl, C 1 ~C 6 -Halogenated alkyl, OC 1 ~C 6 - Selected from alkyl groups; or R 7 and R 8 Together with the C atom to which they are bonded, C 3 ~C 6 -Forms a 3- to 6-membered saturated heterocycle containing 1, 2, or 3 heteroatoms from the group consisting of cycloalkyl or O and S; In each case, X is independently halogen, CN, and C 1 ~C 6 -alkyl, C 1 ~C 6 -Halogenated alkyl, OC 1 ~C 6 -alkyl, OC 1 ~C 6 -Halogen alkyl, C 3 ~C 6 -Cycloalkyl, C 2 ~C 6 -Alkenil, C 2 ~C 6 - Selected from Alkinir; n is 0, 1, 2, or 3, however, R 5 、R 6 、R 7 、R 8 (Not all of them can be H) Compounds thereof, as well as their N-oxides and agriculturally acceptable salts. Section 2 R 2 C 1 ~C 6 -alkyl or OC 1 ~C 6 - A compound that is alkyl, as described in item 1. Section 3 R 2 CH 3 The compound described in item 1 or 2. Section 4 R 3 C 1 ~C 6 -Alkyl or C 1 ~C 6 - A compound selected from halogen alkyls, as described in any one of items 1 to 3. Section 5 R 3 CH 3 or CHF 2 A compound described in any one of items 1 to 4. Section 6 R 5 is H or C 1 ~C 6 - A compound that is alkyl, as described in any one of items 1 to 5. Section 7 R 6 is the aforementioned H or C 1 ~C 6 - A compound selected from alkyl groups, as described in any one of items 1 to 6. Section 8 R 5 and R 6 Together with the C atom to which they are bonded, they form =O or C 3 ~C 6 - Compounds that form a cycloalkyl group, as described in any one of items 1 to 7. Section 9 R 7 is H or C 1 ~C 6 - A compound that is alkyl, as described in any one of items 1 to 8. Item 10 R 8 is the aforementioned C 1 ~C 6 - Selected from alkyl, phenyl, and benzyl, the portion is unsubstituted or has 1 to 3 groups R 5a It is replaced by the 1 to 3 groups R 5a They are independent of each other, OC 1 ~C 6 - A compound selected from alkyl groups, as described in any one of items 1 to 9. Section 11 X is halogen, C 1 ~C 6 -alkyl, OC 1 ~C 6 -alkyl, OC 1 ~C 6 - A compound selected from halogen alkyls, as described in any one of items 1 to 10. Item 12 X is F, CH 3 、C 2 H 5 OCH 3 , OCHF 2 OCF 3 A compound selected from any one of items 1 to 11. Item 13 A composition comprising one compound of formula I as described in any one of items 1 to 12, its N-oxide, or an agriculturally acceptable salt. Item 14 Formula Y:

change

change

Claims

1. Formula I as a disinfectant 【Chemistry 1】 (In the formula, R １ H is; R ２ is, in each case independently, 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, O-C １ to C ６ -alkyl, C ３ to C ６ -cycloalkyl; R ３ In each case, independently, C １ ~C ６ - Alkyl, C １ ~C ６ - Alkyl halogens, C ２ ~C ６ - Alkenil, C ２ ~C ６ - Halogenyl, C ２ ~C ６ -Alkinyl, O-C １ ~C ６ - Alkyl, C ３ ~C ６ - Selected from cycloalkyl groups; R ４ H is; R ５ In each case, independently, H, F, CN, C １ ~C ６ - Alkyl, C １ ~C ６ - Alkyl halogens, C ２ ~C ６ - Selected from alkenyl, phenyl, and benzyl, The aforementioned portion is either unsubstituted or has 1 to 3 bases R ５ａ It is replaced by the 1 to 3 bases R ５ａ These are, independently of each other, halogen, CN, and C １ ~C ６ - Alkyl, C １ ~C ６ -Halogenated alkyl, O-C １ ~C ６ - Selected from alkyl groups; R ６ In each case, independently, H, F, CN, C １ ~C ６ - Alkyl, C １ ~C ６ - Alkyl halogens, C ２ ~C ６ - Selected from alkenyl, phenyl, and benzyl, R ６ The aforementioned portion is either unsubstituted or has 1 to 3 bases R ６ａ It is replaced by the 1 to 3 bases R ６ａ These are, independently of each other, halogen, CN, and C １ ~C ６ - Alkyl, C １ ~C ６ -Halogenated alkyl, O-C １ ~C ６ - Selected from alkyl groups; or R ５ and R ６ They either form an O molecule together with the C atom to which they are bonded; or R ５ and R ６ Together with the C atom to which they are bonded, C ３ ~C ６ - Forms a 3- to 6-membered saturated heterocycle containing one, two, or three heteroatoms from the group consisting of cycloalkyl or O and S; the cycloalkyl or heterocycle is unsubstituted or contains halogens, C １ ~C ６ - Alkyl, C １ ~C ６ - May be substituted with alkyl halogens; R ７ In each case, independently, H, F, CN, C １ ~C ６ - Alkyl, C １ ~C ６ - Alkyl halogens, C ２ ~C ６ - Selected from alkenyl, phenyl, and benzyl, The aforementioned portion is either unsubstituted or has 1 to 3 bases R ７ａ It is replaced by the 1 to 3 bases R ７ａ These are, independently of each other, halogen, CN, and C １ ~C ６ - Alkyl, C １ ~C ６ -Halogenated alkyl, O-C １ ~C ６ - Selected from alkyl groups; R ８ is, in each case, independently selected from H, F, CN, C １ to C ６ -alkyl, C １ to C ６ -haloalkyl, C ２ to C ６ -alkenyl, phenyl, benzyl, The said moiety is unsubstituted or substituted by 1 to 3 groups R ８ａ and the said 1 to 3 groups R ８ａ are, independently of each other, selected from halogen, CN, C １ to C ６ -alkyl, C １ to C ６ -haloalkyl, O-C １ to C ６ -alkyl; or R ７ and R ８ Together with the C atom to which they are bonded, C ３ ~C ６ - Forms a 3- to 6-membered saturated heterocycle containing one, two, or three heteroatoms from the group consisting of cycloalkyl or O and S; In each case, X is independently halogen, CN, and C １ ~C ６ - Alkyl, C １ ~C ６ -Halogenated alkyl, O-C １ ~C ６ -Alkyl, O-C １ ~C ６ - Alkyl halogens, C ３ ~C ６ - Cycloalkyl, C ２ ~C ６ - Alkenil, C ２ ~C ６ - Selected from Alkinir; n is 0, 1, 2, or 3, however, R ５ , R ６ , R ７ , R ８ (Not all of them can be H) Compounds thereof, as well as their N-oxides and agriculturally acceptable salts.

2. R ２ C １ ~C ６ -Alkyl or O-C １ ~C ６ - The compound according to claim 1, wherein it is alkyl.

3. R ２ CH ３ The compound according to claim 1 or 2.

4. R ３ C １ ~C ６ - Alkyl or C １ ~C ６ - A compound according to claim 1, selected from halogen alkyls.

5. R ３ CH ３ or CHF ２ The compound according to claim 1.

6. R ５ is H or C １ ~C ６ - The compound according to claim 1, wherein it is alkyl.

7. R ６ is the aforementioned H or C １ ~C ６ - A compound according to claim 1, selected from alkyl groups.

8. R ５ and R ６ Together with the C atom to which they are bonded, they equal O or C ３ ~C ６ - The compound according to claim 1, which forms a cycloalkyl group.

9. R ７ is H or C １ ~C ６ - The compound according to claim 1, wherein it is alkyl.

10. R ８ C １ ~C ６ - Selected from alkyl, phenyl, and benzyl, the portion is unsubstituted or has 1 to 3 groups R ８ａ It is replaced by the 1 to 3 bases R ８ａ They are independent of each other, O-C １ ~C ６ - A compound according to claim 1, selected from alkyl groups.

11. X is halogen, C １ ~C ６ -Alkyl, O-C １ ~C ６ -Alkyl, O-C １ ~C ６ - A compound according to claim 1, selected from halogen alkyls.

12. X is F, CH ３ , C ２ H ５ , OCH ３ , OCHF ２ OCF ３ A compound according to claim 1, selected from the following.

13. A composition comprising one compound of formula I as described in claim 1, its N-oxide, or an agriculturally acceptable salt.

14. Formula Y: 【Chemistry 2】 (In the formula, R ５ , R ６ , R ７ , R ８ (and Xn is as defined in claim 1, and Haal is a halogen.) A process for preparing the compound of formula I, including the reaction of the compound.

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