Microbicidal Isonicotinamide Derivatives

Abstract

Compounds of formula (I), in which the substituents are as defined in claim 1, useful as pesticides, in particular fungicides. TIFF2024541419000116.tif37156

Description

[Technical field]

[0001] The present invention relates to heteroarylamide derivatives as active ingredients having microbicidal activity, in particular fungicidal activity, for example. The present invention also relates to agrochemical compositions comprising at least one isonicotinamide derivative, processes for the preparation of these compounds and the use of the isonicotinamide derivatives or compositions in agriculture or horticulture for controlling or preventing infestation by phytopathogenic microorganisms, in particular fungi, on plants, harvested food crops, seeds or non-living materials. [Background technology]

[0002] WO 2020 / 109391 discloses the use of pyridazine (thio)amide derivatives for controlling phytopathogenic microorganisms. WO 2021 / 228734 discloses pyrimidine and triazine carboxamide compounds that can be used to control phytopathogenic microorganisms. Summary of the Invention [Means for solving the problem]

[0003] According to the present invention, [ka] (In the formula, R 1 is phenyl substituted by a single substituent selected from C1-C4-alkyl, C1-C2-haloalkyl, C1-C4-alkoxy, C1-C4-alkylsulfanyl, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C2-haloalkoxy, C2-C3-alkenyl, C2-C3-haloalkenyl, C2-C3-alkynyl, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, C2-C3-alkenyloxy and C2-C3-alkynyloxy; or R 1is phenyl optionally substituted with 1, 2 or 3 substituents, which may be the same or different, independently selected from hydroxyl, halogen, mercapto, amino, cyano, methyl, ethyl, propyl, isopropyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, propyloxy, isopropyloxy, tert-butoxy, allyloxypropargyloxymethylsulfanyl, methylsulfonyl, difluoromethoxy, trifluoromethoxy, cyclopropyl, cyclobutyl and cyclopropyloxy; or R 1 is a 6-membered monocyclic heteroaryl ring containing 1, 2 or 3 nitrogen atoms, which heteroaryl ring is optionally substituted with 1 or 2 substituents, which may be the same or different, independently selected from hydroxyl, halogen, mercapto, amino, cyano, C1-C4-alkyl, C1-C2-haloalkyl, C1-C4-alkylsulfanyl, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C2-C3-alkenyl, C2-C3-haloalkenyl, C2-C3-alkynyl, C3-C6-cycloalkyl, C1-C4-alkoxy, C1-C2-haloalkoxy, C2-C3-alkenyloxy, C2-C3-alkynyloxy and C3-C6-cycloalkyloxy; R 2 and R 3 is independently selected from hydrogen, halogen, cyano, hydroxy, C1-C3-alkyl, C1-C3-alkoxy and C1-C2-haloalkoxy; R 4 is phenyl substituted by a single substituent selected from C1-C4-alkyl, C1-C2-haloalkyl, C1-C4-alkoxy, C1-C4-alkylsulfanyl, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C2-haloalkoxy, C2-C3-alkenyl, C2-C3-haloalkenyl, C2-C3-alkynyl, C3-C6-cycloalkyl and C3-C6-cycloalkyloxy; or R 4is phenyl optionally substituted with 1, 2 or 3 substituents, which may be the same or different, independently selected from hydroxyl, halogen, mercapto, amino, cyano, methyl, ethyl, propyl, isopropyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, propyloxy, isopropyloxy, tert-butoxy, allyloxypropargyloxymethylsulfanyl, methylsulfonyl, difluoromethoxy, trifluoromethoxy, cyclopropyl, cyclobutyl and cyclopropyloxy; or R 4 is a 6-membered monocyclic heteroaryl ring containing 1, 2 or 3 nitrogen atoms, the heteroaryl ring being optionally substituted with 1 or 2 substituents, which may be the same or different, independently selected from hydroxyl, halogen, mercapto, amino, cyano, C1-C4-alkyl, C1-C2-haloalkyl, C1-C4-alkoxy, C2-C3-alkenyloxy, C2-C3-alkynyloxy, C1-C4-alkylsulfanyl, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C2-haloalkyloxy, C3-C6-cycloalkyl and C3-C6-cycloalkyloxy; A is (A-1), (A-2), and (A-3): [ka] wherein the jagged line defines the point of attachment to the remainder of the compound of formula (I). Selected from; R 5 is selected from hydrogen, halogen, cyano, C1-C3-alkyl and C1-C3-alkoxy; R 6 is selected from hydrogen, hydroxy, cyano, halogen, C1-C3-alkyl, C2-C3-alkenyl, C2-C3-alkynyl, C1-C3-alkoxy, C1-C3-fluoroalkyl, C1-C3-fluoroalkoxy and C3-C4-cycloalkyl; R 7is selected from hydrogen, halogen, cyano, C1-C3-alkyl and C1-C3-alkoxy; R 8 is selected from hydrogen, hydroxy, cyano, mercaptyl, halogen, C1-C3-alkyl, C2-C3-alkenyl, C2-C3-alkynyl, C1-C3-alkoxy, C1-C3-fluoroalkyl, C1-C3-fluoroalkoxy and C3-C4-cycloalkyl; or R 8 is selected from hydrogen, hydroxy, halo, C1-C4-alkyl, C1-C3-fluoroalkyl, C1-C4-alkoxy, C1-C3-fluoroalkoxy, C3-C4-cycloalkyl, C2-C4-alkenyl, C1-C4-alkylethynyl, C3-C4-cycloalkylethynyl and C2-C4-alkenyloxy; R 9 is selected from hydrogen, hydroxy, halogen, cyano and C1-C3-alkyl or the agrochemically acceptable salts, stereoisomers, enantiomers and N-oxides of the compounds of formula I.

[0004] Surprisingly, it has now been found that the novel compounds of formula (I) have, in fact, a highly advantageous level of biological activity for the protection of plants against diseases caused by fungi. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0005] According to a second aspect of the present invention there is provided an agrochemical composition comprising a fungicidally effective amount of a compound of formula (I). Such an agricultural composition may further comprise at least one additional active ingredient and / or an agrochemically acceptable diluent or carrier.

[0006] According to a third aspect of the present invention there is provided a method for controlling or preventing infestation of useful plants by phytopathogenic microorganisms, comprising applying a fungicidally effective amount of a compound of formula (I), or a composition containing this compound as an active ingredient, to the plant, its part or its habitat.

[0007] According to a fourth aspect of the present invention there is provided the use of a compound of formula (I) as a bactericide or fungicide. According to this particular aspect of the present invention the use may be other than in a method of treatment of the human or animal body by surgery or therapy.

[0008] As used herein, the terms "hydroxyl" or "hydroxy" refer to an --OH group.

[0009] As used herein, the term "mercapto" means a --SH group.

[0010] As used herein, the term "cyano" means a --CN group.

[0011] As used herein, amino refers to the group --NH.

[0012] As used herein, nitro refers to the group --NO.sub.2.

[0013] As used herein, oxo means a =O group (such as in a carbonyl (C=O) group).

[0014] As used herein, the term "halogen" or "halo" refers to fluorine (fluoro), chlorine (chloro), bromine (bromo) or iodine (iodo), preferably fluorine, chlorine or bromine.

[0015] As used herein, "C 1-4 The term "alkyl" refers to a straight or branched hydrocarbon chain radical consisting solely of carbon and hydrogen atoms, containing no unsaturation, having from 1 to 4 carbon atoms, and attached to the remainder of the molecule by a single bond. 1-3 Alkyl should be construed accordingly. 1-4 Examples of alkyl include, but are not limited to, methyl, ethyl, and isopropyl.

[0016] As used herein, "C2-3 The term "alkenyl" refers to a straight or branched hydrocarbon chain radical group consisting solely of carbon and hydrogen atoms, having 2 or 3 carbon atoms, containing at least one double bond which may be in either the (E) or (Z) configuration, attached to the remainder of the molecule by a single bond. 2-3 Examples of alkenyl include, but are not limited to, prop-1-enyl, allyl (prop-2-enyl).

[0017] As used herein, "C 2-3 The term "haloalkenyl" refers to any of the C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C30, C41, C52, C63, C74, C75, C86, C97, C9 2-3 Refers to an alkenyl group.

[0018] As used herein, "C 2-3 The term "alkynyl" refers to a straight or branched hydrocarbon chain radical group consisting solely of carbon and hydrogen atoms, containing at least one triple bond, having two or three carbon atoms and attached to the remainder of the molecule by a single bond. 2-3 Examples of alkynyl include, but are not limited to, prop-1-ynyl and propargyl (prop-2-ynyl).

[0019] As used herein, the term "C 1-3 "Alkoxy" means a group of the formula R a O- radical, where R a is a C 1-3 It is an alkyl radical. C 1-3 Examples of alkoxy include, but are not limited to, methoxy, ethoxy, and isopropoxy.

[0020] As used herein, "C 1-4 The term "haloalkyl" refers to any of the C1 to C2 alkyl groups generally defined above, substituted with one or more of the same or different halogen atoms. 1-4 Refers to the alkyl radical. 1-4Examples of haloalkyl include, but are not limited to, fluoromethyl, fluoroethyl, difluoromethyl, trifluoromethyl, and 2,2,2-trifluoroethyl.

[0021] As used herein, "C 1-3 The term "fluoroalkyl" refers to a C alkyl group, as generally defined above, substituted with one or more fluorine atoms. 1-3 Refers to the alkyl radical. 1-3 Examples of fluoroalkyl include, but are not limited to, difluoromethyl and trifluoromethyl.

[0022] As used herein, the term "C 1-3 "Fluoroalkoxy" means a C as generally defined above substituted with one or more fluorine atoms. 1-3 Refers to alkoxy radicals. C 1-3 Examples of fluoroalkoxy include, but are not limited to, trifluoromethoxy.

[0023] As used herein, "C 3-4 The term "cycloalkyl" refers to a stable monocyclic ring radical that is saturated and contains three or four carbon atoms.

[0024] As used herein, the term "C 1-3 "Alkylsulfanyl" means a group of the formula -SR a In the formula, R a is a C 1-3 It is an alkyl radical.

[0025] As used herein, the term "C 1-3 "Alkylsulfonyl" means a group of the formula -S(O)R a In the formula, R a is a C 1-3 It is an alkyl radical.

[0026] The term "heteroaryl" as used herein refers to a 6-membered aromatic monocyclic ring having 1 or 2 nitrogen atoms. Examples are heteroaryls J-1 to J-9 shown in Table J below.

[0027] Table J: Heteroaryl J-1 to J-9: [ka] The possible presence of one or more asymmetric carbon atoms in the compound of formula (I) means that the compound can be in chiral isomeric form, i.e., enantiomeric or diastereomeric form. Also, the restriction of rotation about a single bond can give rise to atropisomers. Formula (I) is intended to include all these possible isomeric forms and mixtures thereof. The present invention includes all these possible isomeric forms and mixtures thereof of the compound of formula (I). Similarly, formula (I) is intended to include all possible tautomers, if present, including lactam-lactim tautomers and keto-enol tautomers. The present invention includes all possible tautomeric forms of the compound of formula (I).

[0028] In each case, the compounds of formula (I) according to the invention may be in free form, in an oxidized form as an N-oxide, in a covalently hydrated form, or in a salt form, e.g. an agriculturally usable or agrochemically acceptable salt form.

[0029] N-oxides are the oxidized forms of tertiary amines or nitrogen-containing aromatic heterocyclic compounds, as described, for example, in the book "Heterocyclic N-oxides", A. Albini and S. Pietra, CRC Press, Boca Raton 1991.

[0030] The following list refers to the compounds of formula (I) of the present invention and defines the substituents A, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R7 , R 8 and R 9 For any one of these substituents, any of the definitions given below may be combined with any other substituent definition given below or elsewhere in this document.

[0031] As described above, A is (A-1), (A-2), or (A-3): [ka] where the jagged lines define the points of attachment to the remainder of the compound of formula (I). For clarity, it should be understood that the oxygen atoms shown in formulas (A-1), (A-2) and (A-3) are shown only to identify the bonds to the remainder of the compound of formula (I) and that these two oxygen atoms are not part of the group A.

[0032] In the embodiment where A is (A-2), R 7 teeth, A. hydrogen, fluoro, chloro, cyano, methyl, ethyl, methoxy or ethoxy; or B. selected from hydrogen, fluoro, chloro, cyano, methyl, ethyl, methoxy and ethoxy; or C. hydrogen or methyl; or D. selected from hydrogen and methyl; or E. Hydrogen It is.

[0033] In the embodiment where A is (A-2), R 8 teeth, A. selected from hydrogen, hydroxy, cyano, mercaptyl, halogen, C1-C3-alkyl, C2-C3-alkenyl, C2-C3-alkynyl, C1-C3-alkoxy, C1-C3-fluoroalkyl, C1-C3-fluoroalkoxy, and C3-C4-cycloalkyl; or B. selected from hydrogen, hydroxy, halo, C1-C4-alkyl, C1-C4-alkoxy, C3-C4-cycloalkyl, C2-C4-alkenyl, C1-C4-alkylethynyl, C3-C4-cycloalkylethynyl and C2-C4-alkenyloxy; or C. hydrogen, hydroxy, chloro, methyl, ethyl, isopropyl, methoxy, cyclopropyl, isoprenyl, 2-cyclopropylethynyl, 2-methylallyloxy, or isopropoxy; or D. selected from hydrogen, hydroxy, chloro, methyl, ethyl, isopropyl, methoxy, cyclopropyl, isoprenyl, 2-cyclopropylethynyl, 2-methylallyloxy, and isopropoxy; or E. hydrogen, hydroxy, cyano, mercaptyl, fluoro, chloro, methyl or ethyl; or F. selected from hydrogen, hydroxy, cyano, mercaptyl, fluoro, chloro, methyl and ethyl It is.

[0034] In the embodiment where A is (A-2), R 7 and R 8 is the following: AR 7 is selected from hydrogen, fluoro, chloro, cyano, methyl, ethyl, methoxy and ethoxy; R 8 is selected from hydrogen, hydroxy, cyano, mercaptyl, fluoro, chloro, methyl and ethyl; or BR 7 is selected from hydrogen, chloro, methyl and ethyl; R 8 is selected from hydrogen, chloro, fluoro, methyl and ethyl; or CR 7 is selected from hydrogen and methyl; R 8 is selected from hydrogen, chloro, and methyl; or DR 7 is hydrogen, and R 8 is chloro or methyl; or ER 7 is hydrogen, and R 8 is chloro; or FR 7 is hydrogen, and R 8 is methyl; GR 7 is hydrogen, and R 8 is selected from hydrogen, hydroxy, chloro, methyl, ethyl, isopropyl, methoxy, isopropoxy, cyclopropyl, isoprenyl, 2-cyclopropylethynyl, and 2-methylallyloxy. It is defined as follows:

[0035] In one embodiment, A is (A-1), AR 5 is selected from hydrogen, fluoro, chloro, cyano, methyl, ethyl, methoxy and ethoxy; R 6 is selected from hydrogen, hydroxy, cyano, fluoro, chloro, methyl and ethyl; or BR 5 is selected from hydrogen, chloro, methyl and ethyl; R 6 is selected from hydrogen, hydroxy, methyl and ethyl; or CR 5 is selected from hydrogen and methyl; R 6 is selected from hydrogen and methyl; or DR 5 is hydrogen, and R 6 is hydrogen and methyl; or ER 5 is hydrogen, and R 6 is methyl.

[0036] In one embodiment, A is (A-3), where R 9 is selected from hydrogen, hydroxy, chloro, cyano, methyl and ethyl.

[0037] In one embodiment, R 1 teeth, A. phenyl, pyridine, pyrazine, pyrimidine or pyridazine, wherein the phenyl, pyridine, pyrazine, pyrimidine or pyridazine is optionally substituted with one or two substituents, for example one substituent, independently selected from hydroxyl, halogen, mercapto, amino, cyano, methyl, ethyl, propyl, isopropyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, propoxy, isopropoxy, tert-butoxy, allyloxy, propargyloxy, methylsulfanyl, methylsulfonyl, difluoromethoxy, trifluoromethoxy, cyclopropyl, cyclobutyl and cyclopropyloxy; or B. phenyl, pyridine, pyrazine, pyrimidine or pyridazine, wherein the phenyl, pyridine, pyrazine, pyrimidine or pyridazine is optionally substituted with one or two substituents, for example one substituent, independently selected from hydroxyl, halogen, mercapto, amino, cyano, methyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, allyloxy, propargyloxy, difluoromethoxy, trifluoromethoxy, cyclopropyl, cyclobutyl and cyclopropyloxy; or C. phenyl, pyridine, pyrazine, pyrimidine or pyridazine, wherein the phenyl, pyridine, pyrazine, pyrimidine or pyridazine is optionally substituted with one or two substituents, for example one substituent, independently selected from hydroxyl, chloro, fluoro, cyano, methyl, difluoromethyl, trifluoromethyl, methoxy, allyloxy, propargyloxy, difluoromethoxy, trifluoromethoxy, cyclopropyl and cyclopropyloxy; or D. pyridine, pyrazine, pyrimidine or pyridazine, wherein the pyridine, pyrazine, pyrimidine or pyridazine is optionally substituted with one or two substituents, for example one substituent, independently selected from hydroxyl, chloro, fluoro, cyano, methyl, difluoromethyl, trifluoromethyl, methoxy, allyloxy, propargyloxy, difluoromethoxy, trifluoromethoxy, cyclopropyl and cyclopropyloxy; or E. phenyl substituted with one or two substituents independently selected from hydroxyl, chloro, fluoro, cyano, methyl, difluoromethyl, trifluoromethyl, methoxy, allyloxy, propargyloxy, difluoromethoxy, trifluoromethoxy, cyclopropyl, and cyclopropyloxy, e.g., one substituent; or F. phenyl substituted with a single substituent selected from hydroxyl, chloro, fluoro, cyano, methyl, difluoromethyl, trifluoromethyl, methoxy, allyloxy, propargyloxy, difluoromethoxy, trifluoromethoxy, cyclopropyl, and cyclopropyloxy; or G. 2-Fluoro-3-cyclopropylphenyl, 2-fluoro-3-methylphenyl, 2-fluorophenyl, 3-(difluoromethoxy)phenyl, 3-(trifluoromethoxy)phenyl, 2-(trifluoromethyl)pyridin-4-yl, 3-ethoxyphenyl, 3-ethylphenyl, 3-ethynylphenyl, 3-fluorophenyl, 4-(difluoromethoxy)phenyl, 4-(trifluoromethoxy)phenyl, 4-chlorophenyl, 4-cyanophenyl, 4-ethoxyphenyl, 4-ethylphenyl, 4-fluorophenyl, 3-methoxyphenyl, 3,4-dichlorophenyl, 3,4-difluorophenyl, 3,4-dimethoxyphenyl, 3,5-dichlorophenyl, 3,5-difluorophenyl, 3-cyanophenyl, 3,4-difluorophenyl, 3,4-dimethoxyphenyl, 3,5-dichlorophenyl, 3,5-difluorophenyl, 3-cyanophenyl, 2-methylpyrimidin-4-yl, 2-(trifluoromethyl)pyridine -4-yl, 3-(trifluoromethyl)pyridin-2-yl, 3-methoxypyridin-2-yl, 3-methylpyridin-2-yl, 2-chloropyridin-3-yl, 2-chloropyridin-4-yl, 2-cyanopyridin-3-yl, 2-fluoropyridin-3-yl, 2-methoxypyridin-4-yl, 2-methylpyridin-3-yl, 5-(trifluoromethyl)pyridin-3-yl, 5-chloropyridin-3-yl, 5-cyanopyridin-3-yl, 5-cyclopropylpyridin lysin-3-yl, 5-methylpyridin-3-yl, 5-pyridazin-4-yl, 6-(trifluoromethyl)pyridin-3-yl, 6-chloropyridin-2-yl, 6-cyanopyridin-3-yl, 6-cyclopropylpyridin-2-yl, 6-methoxypyridin-3-yl, 6-methyl-2-pyridyl, 6-methylpyridazin-3-yl, 6-methylpyridin-2-yl, 6-methylpyridin-3-yl, pyridin-3-yl, pyridin-4-yl, or phenyl; or H. phenyl, 3-trifluoromethylphenyl, 3-methoxyphenyl, 3-cyclopropylphenyl, 3-cyclopropyl-2-fluorophenyl, or 6-chloropyridin-3-yl; or I. phenyl, 6-chloropyridin-3-yl, 3-trifluoromethylphenyl, 3-methoxyphenyl, or 3-cyclopropylphenyl; or J. Phenyl, 3-methoxyphenyl, or 3-cyclopropylphenyl It is.

[0038] In one embodiment, R 2 teeth, A. hydrogen, chloro, fluoro, methyl, ethyl, cyano, hydroxy, methoxy, ethoxy, methoxymethyl and difluoromethoxy; or B. hydrogen, methyl, hydroxy, methoxy, and difluoromethoxy; or C. Hydrogen is selected from.

[0039] In one embodiment, R 3 teeth, A. hydrogen, chloro, fluoro, methyl, ethyl, cyano, hydroxy, methoxy, ethoxy, methoxymethyl and difluoromethoxy; or B. hydrogen, methyl, hydroxy, methoxy, and difluoromethoxy; or C. Hydrogen is selected from.

[0040] In one embodiment, R 2 and R 3 teeth, A. independently selected from hydrogen, chloro, fluoro, methyl, ethyl, cyano, hydroxy, methoxy, ethoxy, methoxymethyl, and difluoromethoxy; or B. differently selected from hydrogen, chloro, fluoro, methyl, ethyl, cyano, hydroxy, methoxy, ethoxy, methoxymethyl, and difluoromethoxy; or C. independently selected from hydrogen, fluoro, methyl, ethyl, cyano, hydroxy, methoxy, ethoxy, methoxymethyl, and difluoromethoxy; or D. one is hydrogen and the other is selected from chloro, fluoro, methyl, ethyl, cyano, hydroxy, methoxy, ethoxy, methoxymethyl, and difluoromethoxy; or E. one is hydrogen and the other is selected from chloro, fluoro, methyl and ethyl; or F. independently selected from hydrogen and fluoro; or G. one is hydrogen and the other is selected from hydrogen and fluoro; It is.

[0041] In one embodiment, R 4 teeth, A. phenyl, pyridine, pyrazine, pyrimidine or pyridazine, wherein the phenyl, pyridine, pyrazine, pyrimidine or pyridazine is optionally substituted with one or two substituents independently selected from hydroxyl, halogen, mercapto, amino, cyano, methyl, ethyl, propyl, isopropyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, propyloxy, isopropyloxy, tert-butoxy, allyloxy, propargyloxy, methylsulfanyl, methylsulfonyl, difluoromethoxy, trifluoromethoxy, cyclopropyl, cyclobutyl and cyclopropyloxy; or B. phenyl, pyridine, pyrazine, pyrimidine or pyridazine, wherein the phenyl, pyridine, pyrazine, pyrimidine or pyridazine is optionally substituted with one or two substituents independently selected from hydroxyl, halogen, mercapto, amino, cyano, methyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, allyloxy, propargyloxy, difluoromethoxy, trifluoromethoxy, cyclopropyl, cyclobutyl and cyclopropyloxy; or C. phenyl, pyridine, pyrazine, pyrimidine or pyridazine, wherein the phenyl, pyridine, pyrazine, pyrimidine or pyridazine is optionally substituted with one or two substituents independently selected from hydroxyl, chloro, fluoro, cyano, methyl, difluoromethyl, trifluoromethyl, methoxy, allyloxy, propargyloxy, difluoromethoxy, trifluoromethoxy, cyclopropyl and cyclopropyloxy; or D. pyridine, pyrazine, pyrimidine or pyridazine, wherein the pyridine, pyrazine, pyrimidine or pyridazine is optionally substituted with one or two substituents, for example one substituent, independently selected from hydroxyl, chloro, fluoro, cyano, methyl, difluoromethyl, trifluoromethyl, methoxy, allyloxy, propargyloxy, difluoromethoxy, trifluoromethoxy, cyclopropyl and cyclopropyloxy; or E. phenyl substituted with one or two substituents independently selected from hydroxyl, chloro, fluoro, cyano, methyl, difluoromethyl, trifluoromethyl, methoxy, allyloxy, propargyloxy, difluoromethoxy, trifluoromethoxy, cyclopropyl, and cyclopropyloxy, e.g., two substituents; or F. Phenyl substituted with two substituents selected from hydroxyl, chloro, fluoro, cyano, methyl, difluoromethyl, trifluoromethyl, methoxy, allyloxy, propargyloxy, difluoromethoxy, trifluoromethoxy, cyclopropyl, and cyclopropyloxy; or G. Phenyl substituted with two substituents selected from chloro, fluoro, methyl, difluoromethyl, trifluoromethyl, methoxy, allyloxy, propargyloxy, difluoromethoxy, trifluoromethoxy, cyclopropyl, and cyclopropyloxy; or H. 2,4-dichlorophenyl, 3-methylphenyl, 4-methylphenyl, 2,4-dimethylphenyl, 3,4-dimethylphenyl, 2-chloro-4-cyanophenyl, 2-methyl-4-cyanophenyl, 2,4-difluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3-fluorophenyl, 2-cyanophenyl, 3-cyanophenyl, 4-cyanophenyl, 3-methoxyphenyl, 4-methoxyphenyl, 3,4-dimethoxyphenyl, phenyl, 6-chloro-3-pyridyl, 6-cyano-3-pyridyl, 6-methyl-3-pyridyl; or I. 2,4-dichlorophenyl, 2,4-dimethylphenyl, or 6-chloro-3-pyridyl; or J.2,4-Dichlorophenyl It is.

[0042] The compound of the present invention is represented by formula (I-1) or formula (I-2) [ka] (In the formula, R 2 and R 3 are different substituents).

[0043] The compounds of formula (I) according to the present invention can be prepared as shown in the following schemes 1 to 15, unless otherwise specified, in which A, A-1, A-2, A-3, Z 1 , Z 2 , Z 3 , Z 4 , R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 is as defined for compounds of formula (I).

[0044] Compounds of formula (I) can be obtained by an amide coupling conversion between compounds of formula (II) in which X is OH and amine compounds of formula (III) by activating the carboxylic acid function of the compound of formula (II), by converting the -OH of the carboxylic acid into a good leaving group such as a chloride group, for example by using (COCl)2 or SOCl2, prior to treatment with the compound of formula (III), preferably in a suitable solvent (for example N-methylpyrrolidone, acetonitrile, dimethylacetamide, dichloromethane or tetrahydrofuran), at a temperature preferably between 25°C and 60°C, optionally in the presence of a base such as triethylamine or N,N-diisopropylethylamine, or optionally in the presence of a base (for example triethylamine or N,N-diisopropylethylamine), in a suitable solvent (for example acetonitrile), under conditions that are commonly carried out under conditions described in the literature for amide coupling such as 1-propanephosphonic acid cyclic anhydride (T3P). See, for example, Chem.Soc.Rev.(2009), 38, 606 and Chem.Soc.Rev.(2011), 40, 5084. Compounds of formula (II) and compounds of formula (III) are known or commercially available. This is shown in Scheme 1. [ka] Scheme 1

[0045] Compounds of formula (I), where ring A is selected from (A-1), (A-2) or (A-3), are prepared from reacting a nucleophilic compound of formula (IV) with an electrophilic compound of formula (V), where Y is a suitable leaving group such as fluoro, chloro, bromo, iodo, BF3K, B(OH)2 or B(pinacol), in the presence of a base (e.g., KO-t-Bu, K3PO4, K2CO3, triethylamine or Cs2CO3), in a suitable solvent (e.g., N-methylpyrrolidone, dimethylacetamide, acetonitrile, tetrahydrofuran, 2-methyltetrahydrofuran, sulfolane or dimethylsulfoxide), preferably using a metal catalyst complex (e.g., Cu or Pd) at a temperature between 60°C and 110°C. For related examples, see Eur. J. Org. Chem., (2011), 18, 3353; J. Org. Chem., (2009), 74, 7951; Tetrahedron Lett., (2012), 53, 5318. Compounds of formula (IV) are known or commercially available. This is shown in Scheme 2. [ka] Scheme 2

[0046] Compounds of formula (II), in which ring A is selected from (A-1), (A-2) or (A-3) and X is C1-C4-alkoxy, are prepared from reacting a nucleophilic compound of formula (IV) with an electrophilic compound of formula (VI), in which X is OH or C1-C4 alkoxy and Y is a suitable leaving group such as fluoro, chloro, bromo, iodo, BF3K, B(OH)2 or B(pinacol), in the presence of a base (e.g., KO-t-Bu, K3PO4, K2CO3, triethylamine or Cs2CO3), in a suitable solvent (e.g., N-methylpyrrolidone, dimethylacetamide, acetonitrile, tetrahydrofuran, 2-methyltetrahydrofuran, sulfolane, dimethylsulfoxide), preferably using a metal catalyst complex (e.g., Cu or Pd) at a temperature between 60°C and 110°C. For relevant examples, see Eur. J. Org. Chem., (2011), 18, 3353; J. Org. Chem., (2009), 74, 7951; Tetrahedron Lett., (2012), 53, 5318; WO 2008 / 110313 and WO 2012 / 136604. Furthermore, compounds of formula (II) where X is C1-C4-alkoxy are readily hydrolyzed under conditions described in the literature to give compounds of formula (II) where X is OH. Compounds of formula (VI) are known or commercially available. This is shown in Scheme 3. [ka] Scheme 3

[0047] Compounds of formula (V), in which ring A is selected from (A-1), (A-2) or (A-3) and Y is halogen or OH, can be obtained by amide coupling conversion of compounds of formula (VI), in which X is OH and Y is halogen or OH, with amine compounds of formula (III) by activating the carboxylic acid function of the compound of formula (VI), by converting the -OH of the carboxylic acid into a good leaving group such as a chloride group, for example by using (COCl)2 or SOCl2, before treatment with the compound of formula (III), preferably in a suitable solvent (e.g. N-methylpyrrolidone, dimethylacetamide, dichloromethane or tetrahydrofuran), at a temperature preferably between 25° C. and 60° C., optionally in the presence of a base such as triethylamine or N,N-diisopropylethylamine, or in a suitable solvent (e.g. acetonitrile), optionally in the presence of a base (e.g. triethylamine or N,N-diisopropylethylamine), under conditions usually described in the literature for amide coupling such as 1-propanephosphonic acid cyclic anhydride (T3P). See, for example, Chem. Soc. Rev. (2009), 38, 606 and Chem. Soc. Rev. (2011), 40, 5084. This is shown in Scheme 4. [ka] Scheme 4

[0048] Compounds of formula (II) in which ring A is selected from (A-1), (A-2) or (A-3) and X is OH or C1-C4-alkoxy can be prepared by oxidation of the compound with a metal source (e.g., Cu(OAc)2) in a suitable solvent (e.g., dichloromethane, 1,2-dichloromethane, acetonitrile, tetrahydrofuran, 2-methyltetrahydrofuran, N-methylpyrrolidone, dimethylacetamide) at a temperature of 40°C to 80°C, preferably with an oxidizing agent such as O2 or RockPhos Pd It is prepared by reacting a nucleophilic compound of formula (VI) where Y is OH and X is OH or C1-C4-alkoxy with an electrophilic compound of formula (X) where E is fluoro, chloro, bromo, iodo, BF3K, B(OH)2 or B(pinacol) in the presence of a suitable palladium precatalyst such as G3, in the presence of a base (e.g. K3PO4) and a suitable solvent (e.g. dimethyl ether or toluene) at a temperature between 20°C and 80°C. For relevant examples, see Org.Lett., (2003), 5, 1381; Tetrahedron Lett. (1998), 39, 2933; Tetrahedron Lett., (2003), 44, 3863; and Org.Lett., (2013), 15, 2876. Compounds of formula (X) and compounds of formula (VI) are known or commercially available. This is shown in Scheme 5. [ka] Scheme 5

[0049] Compounds of formula (I), wherein ring A is selected from (A-1), (A-2) or (A-3), are prepared by reacting a nucleophilic compound of formula (V) wherein Y is OH with an electrophilic compound of formula (X) wherein E is chloro, bromo, iodo, BF3K, B(OH)2 or B(pinacol) using a metal source (e.g., Cu(OAc)2) optionally in the presence of an oxidant such as O2 or a suitable palladium pre-catalyst such as RockPhos Pd G3, in the presence of a base (e.g., K3PO4) and a suitable solvent (e.g., dimethyl ether or toluene) at a temperature between 20°C and 80°C in a suitable solvent (e.g., dichloromethane, 1,2-dichloromethane, acetonitrile, tetrahydrofuran, 2-methyltetrahydrofuran) at a temperature between 40°C and 80°C. For related examples, see Org.Lett., (2003), 5, 1381; Tetrahedron Lett. (1998), 39, 2933; Tetrahedron Lett., (2003), 44, 3863; and Org.Lett., (2013), 15, 2876. Compounds of formula (X) are known or commercially available. This is shown in Scheme 6. [ka] Scheme 6

[0050] Compounds of formula (VI), where A can be selected from (A-1), (A-2) or (A-3), X is OH or C1-C4-alkoxy, and Y is OH or halogen, can be obtained from compounds of formula (XI), where Y is OH or halogen, by oxidation methods using a suitable oxidizing agent such as KMnO4 or cobalt (II) salts and trihydroxyisocyanuric acid (THICA) in a suitable solvent (e.g., acetic acid) at temperatures between 25°C and 200°C. For relevant examples, see Can. J. Chem. (1978), 56, 1273; WO 2021160470. Compounds of formula (XI) are known or can be prepared as described in Bulletin de la Societe Chimique de France (1972), 8, 3198-202. This reaction is shown in Scheme 7. [ka] A is selected from the following: [ka] Scheme 7

[0051] Compounds of formula (II) where A is selected from (A-1), (A-2) or (A-3), X is OH and Y is OH or halogen can be obtained from compounds of formula (XII) where Y is OH or halogen by oxidation methods using a suitable oxidizing agent such as KMnO4 or a suitable cobalt (II) salt and trihydroxyisocyanuric acid (THICA) in a suitable solvent (e.g., acetic acid) at a temperature between 25°C and 200°C. For relevant examples, see Can. J. Chem. (1978), 56, 1273; WO 2021160470. Compounds of formula (XI) are known or can be prepared as described in Bulletin de la Societe Chimique de France (1972), 8, 3198-3202.

[0052] Further, compounds of formula (XII), where A is selected from (A-1), (A-2) or (A-3), can be prepared by reacting a nucleophilic compound of formula (VI) with an electrophilic compound of formula (XI), where Y is a suitable leaving group such as a halogen, in the presence of a base (e.g., KO-t-Bu, K3PO4, K2CO3, triethylamine or Cs2CO3, in a suitable solvent (e.g., N-methylpyrrolidone, dimethylacetamide, acetonitrile, tetrahydrofuran, 2-methyltetrahydrofuran, sulfolane, dimethylsulfoxide) at temperatures between 25°C and reflux, optionally with a metal catalyst and a ligand complex (e.g., CuI, N,N-dimethylglycine). For relevant examples, see Eur. J. Org. Chem., (2011), 18, 3353; J. Org. Chem., (2009), 74, 7951; Tetrahedron Lett., (2012), 53, 5318; WO 2008 / 110313 and WO 2012 / 136604. Compounds of formula (XI) are known or commercially available. They are depicted in Scheme 8. [ka] A is selected from the following: [ka] Scheme 8

[0053] Compounds of formula (XIII) where X is OH or C1-C4-alkoxy are known or can be obtained from compounds of formula (XIV) where Z is chloro, bromo, or iodo via palladium-catalyzed alkoxycarbonylation transformation using a suitable palladium catalyst complex (e.g., Pd(BINAP)(allyl)Cl) in a carbon monoxide atmosphere (e.g., 1-20 bar) in the presence of a suitable base (e.g., K2CO3) in a suitable solvent system (e.g., dioxane / C1-C4 alkyl-OH) at temperatures between 25°C and 50°C. For relevant examples, see RSC Advances, 2014, 4, 48177-48190; Organic Letters, 2009, 11, 1321-1324.

[0054] Furthermore, compounds of formula (I-1b) can be obtained from compounds of formula (XIV) where X is chloro, bromo, or iodo and amines of formula (III) by palladium-catalyzed aminocarbonylation transformation using a suitable palladium catalyst complex (e.g., PEPPSI™-IPr catalyst or XantPhos-linked Pd catalyst precursor) in the presence of a suitable base (e.g., K2CO3) in a suitable solvent (e.g., dioxane) at a temperature of 25°C to 35°C, under carbon monoxide atmosphere (e.g., 1 to 20 bar). For related examples, see Fang, W. et al Org. Lett., 2013, 15, 3678; Friis, D. et al Org. Lett., 2014, 16, 4296-4299. This reaction is shown in Scheme 9. [ka] Scheme 9

[0055] Compounds of formula (XIV), wherein Y is OH or halogen and Z, which may be the same or different, are halogen, are prepared by reacting a nucleophilic compound of formula (VI) with an electrophilic compound of formula (XV) in the presence of a base (e.g., KO-t-Bu, K3PO4, K2CO3, triethylamine or Cs2CO3) in a suitable solvent (e.g., N-methylpyrrolidone, dimethylacetamide, acetonitrile, tetrahydrofuran, 2-methyltetrahydrofuran, sulfolane, dimethylsulfoxide) at a temperature between 25°C and reflux, optionally using a metal catalyst and a ligand complex (e.g., CuI,N,N-dimethylglycine). For relevant examples, see Eur. J. Org. Chem., (2011), 18, 3353; J. Org. Chem., (2009), 74, 7951; Tetrahedron Lett., (2012), 53, 5318; WO 2008 / 110313 and WO 2012 / 136604. Compounds of formula (XV) are known or commercially available.

[0056] Furthermore, compounds of formula (XIV) where Z is as above are readily converted from compounds of formula (XV) where Y is each OH using POCl3 or a suitable alkylating reagent (e.g., MeI or Me2SO4) under conditions described in the literature, as shown in Scheme 10. [ka] Scheme 10

[0057] Alternatively, compounds of formula (I-1a) are prepared by treating compounds of formula (XVII) where Y is chloro, bromo, iodo with a suitable organometallic (e.g., MeMgBr, vinylMgCl, AlMe3) or organometallic (e.g., trimethylboroxine) reagent in a suitable solvent such as toluene or 2-methyltetrahydrofuran, optionally in the presence of a base (e.g., K2CO3), in the presence of a suitable metal adduct (e.g., CuBr) or catalyst complex (e.g., 1,1'-bis(diphenylphosphino)ferrocene-palladium(II) dichloride) at temperatures between 50°C and reflux. See, for example, J. Org. Chem. (1987), 52, 3847; WO 2006 / 045514; WO 2004 / 080998.

[0058] Furthermore, R 6 Compounds of formula (I-1a) where is C1-C4-alkoxy are prepared by treating compounds of formula (XVII) where is halogen with a suitable C1-C4 alkyl-OH solvent in the presence of a base such as NaH, KO-t-Bu, K3PO4, K2CO3, triethylamine, or Cs2CO3, optionally in the presence of an additional solvent (e.g., N-methylpyrrolidone, dimethylacetamide, acetonitrile, tetrahydrofuran, 2-methyltetrahydrofuran, sulfolane, dimethylsulfoxide) at temperatures between 20°C and reflux. For related examples, see F. Terrier, Modern Nucleophilic Aromatic Substitution, Wiley-VCH, Weinheim, 2013. This is shown in Scheme 11. [ka] Scheme 11

[0059] Compounds of formula (I-1b) are prepared by treating compounds of formula (XVIII) where Z is chloro, bromo, iodo with a suitable organometallic (e.g., Zn(CN)2, cyclopropylMgBr, MeZnCl, AlMe3) or organometalloid (e.g., trimethylboroxine) reagent in the presence of a suitable metal (e.g., CuBr) or catalyst complex (e.g., 1,1'-bis(diphenylphosphino)ferrocene-palladium(II) dichloride) optionally in the presence of a base (e.g., K2CO3) in an inert solvent such as toluene or 2-methyltetrahydrofuran at temperatures between 35°C and reflux. See, e.g., J. Org. Chem. (1987), 52, 3847; WO 2006 / 045514; WO 2004 / 080998.

[0060] Furthermore, R 8 Compounds of formula (I-1b) where Y is C1-C4-alkoxy are prepared by treating compounds of formula (XVIII) where Y is halogen with a suitable C1-C4 alkyl-OH solvent in the presence of a base such as NaH, KO-t-Bu, K3PO4, K2CO3, triethylamine, or Cs2CO3, optionally in the presence of an additional solvent (e.g., N-methylpyrrolidone, dimethylacetamide, acetonitrile, tetrahydrofuran, 2-methyltetrahydrofuran, sulfolane, dimethylsulfoxide), at temperatures between 20°C and reflux. For related examples, see F. Terrier, Modern Nucleophilic Aromatic Substitution, Wiley-VCH, Weinheim, 2013.

[0061] Furthermore, compounds of formula (I-1b) where X is C1-C4-alkoxy are readily accessible from compounds of formula (XVIII) where Y is OH via conditions described in the literature using appropriate alkylating reagents (e.g., MeI, Me2SO4), respectively, as shown in Scheme 12. [ka] Scheme 12

[0062] Compounds of formula (XIX) where X is OH or C1-C4-alkoxy and Z is chloro, bromo, iodo are prepared by treating compounds of formula (XX) where X is OH or C1-C4-alkoxy and Z is chloro, bromo, iodo with a suitable organometallic (e.g. vinylMgBr, cyclopropylMgCl, AlMe3) or organometalloid (e.g. trimethylboroxine) reagent in the presence of a suitable metal source (e.g. CuBr) or catalyst complex (e.g. 1,1'-bis(diphenylphosphino)ferrocene-palladium(II) dichloride) and optionally in the presence of a base (e.g. K2CO3) in an inert solvent such as toluene or Me-THF at a temperature between 80°C and 110°C. For relevant examples, see J.Org.Chem.(1987),52,3847; WO 2006 / 045514; WO 2004 / 080998. This is shown in Scheme 13. [ka] Scheme 13

[0063] Compounds of formula (XIIII) where X is OH or C1-C4-alkoxy and Y is OH or halogen are prepared by treating compounds of formula (XIX) where Z is bromo, iodo and Y is fluoro, chloro or bromo, preferably chloro, with a suitable organometallic (e.g. MeMgBr, MeZnCl, AlMe3) or organometalloid (e.g. trimethylboroxine) reagent in the presence of a suitable metal source (e.g. CuBr) or catalyst complex (e.g. 1,1'-bis(diphenylphosphino)ferrocene-palladium(II) dichloride), optionally in an inert solvent such as toluene or 2-methyltetrahydrofuran, in the presence of a base (e.g. K2CO3), at a temperature between 60°C and 110°C. J.Org.Chem.(1987),52,3847; WO 2006 / 045514; WO 2004 / 080998.

[0064] Furthermore, compounds of formula (XIII) where X is OH or C1-C4-alkoxy and Y is halogen or C1-C4-alkoxy are readily accessible from compounds of formula (XIX) where Y is OH using POCl3 and POBr3 or suitable alkylating reagents (e.g. MeI, Me2SO4), respectively, via conditions described in the literature, as shown in Scheme 14. [ka] Scheme 14

[0065] Compounds of formula (XIX) where X is C1-C4-alkoxy are known or can be obtained from compounds of formula (XXII) where Z is chloro, bromo, or iodo via palladium-catalyzed alkoxycarbonylation transformation using a suitable palladium catalyst complex (e.g., Pd(BINAP)(allyl)Cl) in a carbon monoxide atmosphere (e.g., 1-20 bar) in the presence of a suitable base (e.g., K2CO3) in a suitable solvent system (e.g., dioxane / C1-C4 alkyl-OH) at temperatures between 25°C and 50°C. For relevant examples, see RSC Advances, 2014, 4, 48177-48190; Organic Letters, 2009, 11, 1321-1324.

[0066] Furthermore, compounds of formula (XXII) in which Z is as defined above are known, commercially available, or can be purchased from the 1 They are either prepared from compounds of formula (XXIII) where Y is a suitable functional group such as OH, nitro, halogen, BF3K, B(OH)2 or B(pinacol) via the techniques described in the scheme above used to introduce the -O-(A) motif.

[0067] Furthermore, compounds of formula (I-1a) can be obtained from compounds of formula (XXII) where Z is chloro, bromo, or iodo and amines of formula (III) by palladium-catalyzed aminocarbonylation transformation using a palladium catalyst complex (e.g., PEPPSI™-IPr catalyst or XantPhos-linked Pd catalyst precursor) in the presence of a suitable base (e.g., K2CO3) in a suitable solvent (e.g., dioxane) at a temperature of 25°C to 35°C, under carbon monoxide atmosphere (e.g., 1 to 20 bar). For related examples, see Fang, W. et al Org. Lett., 2013, 15, 3678; Friis, D. et al Org. Lett., 2014, 16, 4296-4299. This reaction is shown in Scheme 15. [ka] Scheme 15

[0068] As already indicated, it has now been surprisingly found that the compounds of formula (I) according to the invention have a very advantageous level of biological activity in the protection of plants against diseases caused by fungi.

[0069] The compounds of formula (I) can be used in the agricultural sector and related fields of use, for example as active ingredients for the control of plant pests or non-living materials, for the control of spoilage microorganisms or organisms potentially harmful to humans. The novel compounds are distinguished by their excellent activity at low application rates, their excellent tolerance by plants, and their safety for the environment. They have highly useful curative, preventive and systemic properties and can be used to protect numerous cultivated plants. The compounds of formula (I) can be used to inhibit or eliminate pests occurring on plants or plant parts (fruits, flowers, leaves, stems, tubers, roots) of different crops of useful plants, while at the same time also protecting these parts of later-growing plants from, for example, phytopathogenic microorganisms.

[0070] The present invention further relates to a method for controlling or preventing infestation of susceptible plants or plant propagation material and / or harvested food crops by treating the plants or plant propagation material and / or harvested food crops, wherein an effective amount of a compound of formula (I) is applied to the plant, its part or its habitat.

[0071] The compounds of formula (I) may also be used as fungicides. The term "fungicide" as used herein means a compound that controls, modifies or prevents fungal growth. The term "fungicidally effective amount" as used herein means the amount of such a compound or combination of such compounds that is capable of producing an effect on fungal growth. A controlling or modifier effect includes any deviation from natural development such as killing, retardation, etc., and prevention includes the formation of a barrier or other defense in the plant to prevent infection by fungi.

[0072] It may also be possible to use the compounds of formula (I) as dressings for treating plant propagation material, such as seeds, such as fruits, tubers or grains, or plant cuttings, for protection against fungal infections occurring in the soil, as well as against phytopathogenic fungi. The propagation material can be treated with a composition comprising a compound of formula (I) before planting: for example, seeds can be dressed before being sown. The active compounds of formula (I) can also be applied to grains (coating) by impregnating the seeds in a liquid formulation or coating the seeds with a solid formulation. The composition can also be applied to the planting site when the propagation material is planted, for example in the sowing furrow during sowing. The present invention also relates to a method for treating such plant propagation material, and to the plant propagation material thus treated.

[0073] Furthermore, the compounds of formula (I) can be used for controlling fungi, for example in the protection of industrial materials, including wood and wood-based industrial products, food storage, hygiene and other related fields.

[0074] In addition, the present invention can be used to protect non-living materials such as timber, wallboard and paint from fungal attack.

[0075] The compounds of formula (I) are effective against, for example, fungi and fungal vectors involved in diseases, as well as phytopathogenic bacteria and viruses, such as, for example:

[0076] Absidia corymbifera, Alternaria spp., Aphanomyces spp., Ascochyta spp., Aspergillus spp. including A. flavus, A. fumigatus, A. nidulans, A. niger, A. terrus, Aureobasidium spp. including A. pullulans, Blastomyces dermatitidis, Blumeria graminis, Bremia lactucae, lactucae, B. dothidea, B. obtusa, Botryosphaeria spp. including B. cinerea, C. albicans, C. glabrata, C. krusei, C. lusitaniae, C. parapsilosis, C. tropicalis, Candida spp., Cephaloascus fragrans, Ceratocystis spp. spp., Cercospora spp. including C. arachidicola, Cercosporidium personatum, Cladosporium spp., Claviceps purpurea, Coccidioides immitis, Cochliobolus spp., C. musae, C.Colletotrichum spp. including Colletotrichum spp., Cryptococcus neoformans, Diaporthe spp., Didymella spp., Drechslera spp., Elsinoe spp., Epidermophyton spp., Erwinia amylovora, Erysiphe spp. including E. cichoracearum, Eutypa Fusarium spp. including F. lata, F. culmorum, F. graminearum, F. langsethiae, F. moniliforme, F. oxysporum, F. proliferatum, F. subglutinans, and F. solani, Gaeumannomyces graminis, Gibberella fujikuroi, Gloeodes pomigena, Gloeosporium musarum, Glomerella cingulate, Guignardia bidwellii, Gymnosporangium juniperi-virginianae, Helminthosporium spp., Hemileia spp., Histoplasma spp. including H. capsulatum.), Laetisaria fuciformis, Leptographium lindbergi, Leveillula taurica, Lophodermium seditiosum, Microdochium nivale, Microsporum spp., Monilinia spp., Mucor spp., M. graminicola, Mycosphaerella spp. including M. pomi, Oncobasidium theobromaeon, Ophiostoma piceae, Paracoccidioides spp., Penicillium spp. including P. digitatum, P. italicum, Petriellidium spp., Peronosclerospora spp. including P. maydis, P. philippinensis and P. sorghi, Peronosclerospora spp., Phaeosphaeria nodorum, Phakopsora pachyrhizi, Phellinus ignialus igniarus, Phialophora spp., Phoma spp., Phytophthora spp. including Phomopsis viticola, P. infestans, Plasmopara spp. including P. halstedii, P. viticola.), Pleospora spp., Podosphaera spp. including P. leucotricha, Polymyxa graminis, Polymyxa betae, Pseudocercosporella herpotrichoides, Pseudomonas spp., Pseudoperonospora spp. including P. cubensis, P. humuli, Pseudopezizatrakeiphila spp. Puccinia spp., including P. tracheiphila, P. hordei, P. recondita, P. striiformis, P. triticina, Pyrenopeziza spp., Pyrenophora spp., Pyricularia spp., including P. oryzae, Pythium spp., including P. ultimum, Ramularia spp., Rhizoctonia spp., Rhizomucor pusillus, Rhizopus arizus, arrhizus, Rhynchosporium spp., Scedosporium spp. including S. apiospermum and S. prolificans, Schizothyrium pomi, Sclerotinia spp., Sclerotium spp., S. nodorum, S. tritici, S.Septoria spp. (including Septoria tritici), Sphaerotheca macularis, Sphaerotheca fusca (Sphaerotheca fuliginea), Sporothorix spp., Stagonospora nodorum, Stemphylium spp., Stereum hirsutum, Thanatephorus cucumeris, Thielaviopsis basicola, Tilletia spp. spp., Trichoderma spp., including T. harzianum, T. pseudokoningii, T. viride, Trichophyton spp., Typhula spp., Uncinula necator, Urocystis spp., Ustilago spp., Venturia spp., including V. inaequalis, Verticillium spp. and Xanthomonas spp..

[0077] The compounds of formula (I) may be used, for example, in turf, ornamental crops such as flowers, shrubs, broadleaf or evergreen trees such as conifers, as well as in tree injections, pest control, and the like.

[0078] Within the scope of the present invention, the target crops and / or useful plants to be protected are typically berry plants, such as blackberries, blueberries, cranberries, raspberries and strawberries; cereals, such as barley, maize (corn), millet, oats, rice, rye, sorghum, triticale and wheat; fibre plants, such as cotton, flax, hemp, jute and sisal; agricultural crops, such as sugar and fodder beet, coffee, hops, mustard, oilseed rape (canola), poppy, sugarcane, sunflower, tea and tobacco; fruit trees, such as apple, apricot, avocado, banana, cherry, citrus, nectarine, peach, pear and plum; and arable plants, such as bermuda grass, strawberry bush, bentgrass, centipede grass, fescue, ryegrass, lawn grass and wild grass. herbs such as basil, borage, chives, coriander, lavender, lovage, mint, oregano, parsley, rosemary, sage and thyme; legumes such as beans, lentils, peas and soybeans; nuts such as almonds, cashews, peanuts, hazelnuts, peanuts, pecans, pistachios and walnuts; palms such as oil palm; ornamental plants such as flowers, shrubs and trees; other trees such as cocoa, coconut, olive and rubber; vegetables such as asparagus, eggplant, broccoli, cabbage, carrots, cucumber, garlic, lettuce, squash, melon, okra, onion, pepper, potato, pumpkin, rhubarb, spinach and tomato; and perennial and annual crops such as vines, for example grapes.

[0079] The term "useful plants" should also be understood to include useful plants in which resistance to herbicides such as bromoxynil or to a class of herbicides (e.g. HPPD inhibitors, ALS inhibitors such as primisulfuron, prosulfuron and trifloxysulfuron, EPSPS (5-enol-pyroyl-shikimate-3-phosphate-synthase) inhibitors, GS (glutamine synthetase) inhibitors or PPO (protoporphyrinogen-oxidase) inhibitors, etc.) has been provided by conventional breeding or genetic engineering methods. An example of a crop in which resistance to imidazolinones, e.g. imazamox, has been provided by conventional breeding methods (mutagenesis) is Clearfield® summer rapeseed (canola). Examples of crops that have been rendered resistant to herbicides or classes of herbicides by genetic engineering methods include glyphosate- and glufosinate-tolerant corn varieties commercially available under the trade names RoundupReady®, Herculex I®, and LibertyLink®.

[0080] The term "useful plants" should also be understood to include useful plants that have been transformed using recombinant DNA techniques with the ability to synthesize one or more selectively acting toxins, such as those known to be derived from toxin-producing bacteria, particularly those from the genus Bacillus.

[0081] Examples of such plants are YieldGard® (a corn variety expressing a CryIA(b) toxin); YieldGard Rootworm® (a corn variety expressing a CryIIIB(b1) toxin); YieldGard Plus® (a corn variety expressing CryIA(b) and CryIIIB(b1) toxins); Starlink® (a corn variety expressing a Cry9(c) toxin); Herculex I® (a corn variety expressing a CryIF(a2) toxin and the enzyme phosphinothricin N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (a cotton variety expressing a CryIA(c) toxin); Bollgard I® (a cotton variety expressing a CryIA(c) toxin); Bollgard II® (a cotton variety expressing CryIA(c) and CryIIA(b) toxins); VIPCOT® (a cotton variety expressing VIP toxin); NewLeaf® (a potato variety expressing CryIIIA toxin); NatureGard® Agrisure® GT Advantage (GA21 glyphosate-tolerant trait), Agrisure® CB Advantage (Bt11 corn borer (CB) trait), Agrisure® RW (corn rootworm trait), and Protecta®.

[0082] The term "crop plant" should also be understood to include crop plants that have been transformed, using recombinant DNA techniques, so as to have the ability to synthesize one or more selectively acting toxins, such as those known to be derived from toxin-producing bacteria, particularly bacteria of the genus Bacillus.

[0083] Toxins which can be expressed by such transformed plants include, for example, insecticidal proteins from Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis, such as d-endotoxins, for example Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), for example Vip1, Vip2, Vip3 or Vip3A; or insecticidal proteins from Photorhabdus spp. or Xenorhabdus spp., for example Photorhabdus luminescens, Xenorhabdus nematophilus. spp.); toxins produced by animals such as scorpion toxins, spider toxins, wasp toxins and other insect-specific neurotoxins; toxins produced by fungi such as Streptomycete toxins, plant lectins such as pea lectin, barley lectin or snowdrop lectin; agglutinins; proteinase inhibitors such as trypsin inhibitors, serine protease inhibitors, patatin, cystatin, papain inhibitors; ricin, Ribosome-inactivating proteins (RIPs) such as maize-RIP, abrin, rufin, saporin or bryodin; steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidase, ecdysone inhibitors, HMG-COA-reductase, ion channel blockers such as sodium or calcium blockers, juvenile hormone esterase, diuretic hormone receptor, stilbene synthase, bibenzyl synthase, chitinase and glucanase.

[0084] Furthermore, in the context of the present invention, d-endotoxins, such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or trophic insecticidal proteins (Vip), such as Vip1, Vip2, Vip3 or Vip3A, are also to be understood as being particularly hybrid toxins, truncated toxins and modified toxins. Hybrid toxins are recombinantly produced by new combinations of different domains of these proteins (see, for example, WO 02 / 15701). Truncated toxins, such as truncated Cry1Ab, are known. In the case of modified toxins, one or more amino acids of the natural toxin are replaced. In such amino acid substitutions, preferably a non-naturally occurring protease recognition sequence is inserted into the toxin, for example, in the case of Cry3A055, a cathepsin-G recognition sequence is inserted into the Cry3A toxin (see WO 03 / 018810).

[0085] Examples of such toxins or transformed plants capable of synthesizing such toxins are disclosed, for example, in EP 0 374 753, WO 93 / 07278, WO 95 / 34656, EP 0 427 529, EP 451 878 and WO 03 / 052073.

[0086] The processes for the preparation of such transformed plants are generally known to those skilled in the art and are described, for example, in the above-mentioned publications. CryI-type deoxyribonucleic acids and their preparation are known, for example, from WO 95 / 34656, EP 0 367 474, EP 0 401 979 and WO 90 / 13651.

[0087] The toxins contained in the transformed plants confer resistance to harmful insects on the plants, which can be from any taxonomic group of insects, but are particularly commonly found among beetles (Coleoptera), two-winged insects (Diptera), and butterflies (Lepidoptera).

[0088] Transgenic plants containing one or more genes encoding insecticide resistance and expressing one or more toxins are known, and some are commercially available. Examples of such plants include: YieldGard® (a corn variety expressing Cry1Ab toxin); YieldGard Rootworm® (a corn variety expressing Cry3Bb1 toxin); YieldGard Plus® (a corn variety expressing Cry1Ab and Cry3Bb1 toxins); Starlink® (a corn variety expressing Cry9C toxin); Herculex I® (a corn variety expressing Cry1Fa2 toxin and the enzyme phosphinothricin N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (a cotton variety expressing Cry1Ac toxin); Bollgard I® (a cotton variety expressing Cry1Ac toxin); Bollgard II® (a cotton variety expressing Cry1Ac and Cry2Ab toxins); VipCot® (a cotton variety expressing Vip3A and Cry1Ab toxins); NewLeaf® (a potato variety expressing Cry3A toxin); NatureGard®, Agrisure® GT Advantage (GA21 glyphosate-tolerant trait), Agrisure® CB Advantage (Bt11 corn borer (CB) trait), and Protecta®.

[0089] Further examples of such transformed crops are: 1. Bt11 maize, registration number C / FR / 96 / 05 / 10, manufactured by Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France. A genetically engineered maize (Zea mays) that is resistant to the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of a truncated Cry1Ab toxin. Bt11 maize also achieves tolerance to the herbicide glufosinate ammonium by transgenic expression of the enzyme PAT.

[0090] 2. Bt176 maize, registration number C / FR / 96 / 05 / 10, from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France. A genetically engineered maize (Zea mays) that is resistant to the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) by transgenic expression of the Cry1Ab toxin. Bt176 maize also transgenicly expresses the enzyme PAT to achieve tolerance to the herbicide glufosinate ammonium.

[0091] 3. MIR604 maize, registration number C / FR / 96 / 05 / 10, from Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France. Maize conferred insect resistance by transgenic expression of a modified Cry3A toxin. The toxin is Cry3A055 modified by the insertion of a cathepsin-G-protease recognition sequence. The preparation of such transformed maize plants is described in WO 03 / 018810.

[0092] 4. MON863 maize, registration number C / DE / 02 / 9, from Monsanto Europe SA 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium. MON863 expresses the Cry3Bb1 toxin and confers resistance to certain coleopteran insects.

[0093] 5. IPC531 Cotton made by Monsanto Europe SA 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium, registration number C / ES / 96 / 02.

[0094] 6. 1507 Maize from Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium, registration number C / NL / 00 / 10. Maize genetically engineered for expression of the protein Cry1F to achieve resistance to certain lepidopteran insects, and for expression of the PAT protein to achieve resistance to the herbicide glufosinate ammonium.

[0095] 7. NK603 x MON810 maize, registration number C / GB / 02 / M3 / 03, from Monsanto Europe SA 270-272 Avenue de Tervuren, B-1150 Brussels, Belgium. It consists of a conventional hybrid maize variety by crossing the genetically engineered varieties NK603 and MON810. NK603 x MON810 maize transgenic expresses the protein CP4 EPSPS from the strain CP4 of Agrobacterium sp., which confers resistance to the herbicide Roundup® (containing glyphosate), and the Cry1Ab toxin from Bacillus thuringiensis subsp. kurstaki, which confers resistance to certain Lepidoptera, including the European corn borer.

[0096] As used herein, the term "habitat" refers to the field in which the plant is growing or in which the seeds of the cultivated plant have been sown or in which the seeds will be sown in the soil, including the soil, the seeds and seedlings, as well as the established vegetation.

[0097] The term "plant" refers to all physical parts of a plant, including seeds, seedlings, seedlings, roots, tubers, stems, stalks, foliage and fruits.

[0098] The term "plant propagation material" is understood to refer to reproductive parts of plants, such as seeds, which can be used for their propagation, and vegetative bodies, such as cuttings or tubers, for example potatoes. For example, seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes and plant parts may be mentioned. Also mentioned are sprouted plants and shoots that are to be transplanted after germination or emergence from the soil. These shoots may be protected by a complete or partial treatment by immersion before transplantation. Preferably, "plant propagation material" is understood to refer to seeds.

[0099] The compounds of formula (I) can be used in their pure form or, preferably, together with the auxiliaries that are conveniently employed in the art of formulation.For this purpose, they can be conveniently formulated in a known manner into emulsifiable concentrates, coating pastes, directly sprayable or dilutable solutions or suspensions, dilute emulsions, wettable powders, soluble powders, dusts, granules, and capsules, for example, in polymeric materials.As well as the type of composition, the application method, such as spraying, misting, dusting, scattering, coating, or pouring, is selected according to the intended purpose and the current situation.The composition may also contain further auxiliaries, such as stabilizers, defoamers, viscosity regulators, binders or adhesives, as well as fertilizers, sources of trace elements, or other compounds for obtaining special effects.

[0100] Suitable carriers and adjuvants, for example for use in agriculture, can be solid or liquid and are substances useful in formulation technology, such as natural or regenerated mineral substances, solvents, dispersants, wetting agents, adhesives, thickeners, binders or fertilizers. Such carriers are described, for example, in WO 97 / 33890.

[0101] Suspension concentrates are aqueous formulations in which fine solid particles of the active compound are suspended. Such formulations contain anti-settling and dispersing agents and may further contain wetting agents to enhance activity, as well as anti-foaming agents and crystal growth inhibitors. In use, these concentrates are diluted in water and usually applied by spray to the area to be treated. The amount of active ingredient may range from 0.5% to 95% of the concentrate.

[0102] Wettable powders are in the form of fine particles that disperse easily in water or other liquid carriers. These particles contain the active ingredient held in a solid matrix. Typical solid matrices include Fuller's earth, kaolin clay, silica and other easily wet organic or inorganic solids. Wettable powders usually contain 5% to 95% of the active ingredient and small amounts of wetting agents, dispersing agents or emulsifying agents.

[0103] Emulsifiable concentrates are homogeneous liquid compositions that are dispersible in water or other liquids and may consist solely of the active compound and a liquid or solid emulsifier, or may contain a liquid carrier such as xylene, high boiling aromatic naphtha, isophorone, and other non-volatile organic solvents. In use, these concentrates are dispersed in water or other liquid and usually applied as a spray to the area to be treated. The amount of active ingredient may range from 0.5% to 95% of the concentrate.

[0104] Granular formulations include both extrudates and relatively coarse particles, and are usually applied undiluted to the area where treatment is required. Typical carriers for granular formulations include sand, Fuller's earth, attapulgite clay, bentonite clay, montmorillonite clay, vermiculite, perlite, calcium carbonate, brick, pumice, pyrophyllite, kaolin, dolomite, gypsum, wood flour, ground corn cobs, ground peanut shells, sugar, sodium chloride, sodium sulfate, sodium silicate, sodium borate, magnesia, mica, iron oxide, zinc oxide, titanium oxide, antimony oxide, cryolite, gypsum, diatomaceous earth, calcium sulfate, and other organic or inorganic materials that can absorb or be coated with the active compound. Granular formulations usually contain 5% to 25% active ingredient, which may include surfactants such as high-boiling aromatic naphtha, kerosene and other petroleum fractions, or vegetable oils; and / or spreading agents such as dextrin, glue or synthetic resins.

[0105] Dusts are free-flowing admixtures of the active ingredient and finely divided solids such as talc, clays, powders and other organic and inorganic solids which act as dispersants and carriers.

[0106] Microcapsules are typically droplets or granules of active ingredient enclosed in an inert porous shell that allows the encapsulated material to be released into the environment at a controlled rate. The encapsulated droplets are typically 1-50 microns in diameter. The encapsulated liquid typically constitutes 50-95% of the capsule's weight and may contain a solvent in addition to the active compound. Encapsulated granules are generally porous granules with a porous membrane that seals the pore openings of the granule and retains the active species in liquid form within the pores of the granule. The granules are typically in the range of 1 millimeter to 1 centimeter in diameter, preferably 1-2 millimeters. Granules are formed by extrusion, agglomeration or prilling, or are natural. Examples of such materials are vermiculite, calcined clay, kaolin, attapulgite clay, sawdust, and granular carbon. Shell or membrane materials include natural and synthetic rubbers, cellulosic materials, styrene-butadiene copolymers, polyacrylonitriles, polyacrylates, polyesters, polyamides, polyureas, polyurethanes and starch xandates.

[0107] Other useful formulations for agricultural chemical applications include simple solutions of the active ingredient in solvents such as acetone, alkylated naphthalenes, xylenes and other organic solvents in which complete dissolution at the desired concentration is achieved. Pressurized sprayers may also be used in which the active ingredient is dispersed in finely divided form as the low boiling dispersant solvent carrier evaporates.

[0108] Suitable agricultural adjuvants and carriers useful in formulating the compositions of the present invention in the formulation types described above are well known to those skilled in the art.

[0109] Liquid carriers that may be utilized include, for example, water, toluene, xylene, petroleum naphtha oil, crop oil, acetone, methyl ethyl ketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetates, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkyl pyrrolidinone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1,1,1-Trichloroethane, 2-heptanone, alpha-pinene, d-limonene, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, gamma-butyrolactone, glycerol, glycerol diacetate, glycerol monoacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate, isooctane, isophorone, isopropylbenzene, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxy-propanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, methylene chloride, m-xylene, n-hexane, n-octylamine, kutadeca Examples of suitable solvents include ethyl acetate, octylamine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol (PEG400), propionic acid, propylene glycol, propylene glycol monomethyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylene sulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, methanol, ethanol, isopropanol, and higher molecular weight alcohols such as amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, etc., ethylene glycol, propylene glycol, glycerin, and N-methyl-2-pyrrolidinone. For dilution of concentrates, water is the typical carrier of choice.

[0110] Suitable solid carriers include, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, Kieselguhr, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, Fuller's earth, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, walnut hulls, and lignin.

[0111] A wide range of surfactants may be advantageously utilized in both the liquid and solid compositions, particularly those designed to be diluted with a carrier prior to application. These surfactants, when used, typically comprise from 0.1% to 15% by weight of the formulation. They may be anionic, cationic, nonionic or polymeric in nature and may be utilized as emulsifying agents, wetting agents, suspending agents, or for other purposes. Typical surfactants include alkyl sulfates such as diethanolammonium lauryl sulfate; alkylaryl sulfonate salts such as calcium dodecylbenzene sulfonate; alkylphenol-alkylene oxide adducts such as nonylphenol-C.sub.18 ethoxylate; alcohol-alkylene oxide adducts such as tridecyl alcohol-C.sub.16 ethoxylate; soaps such as sodium stearate; alkylnaphthalene sulfonates such as sodium dibutylnaphthalene sulfonate; dialkyl esters of sulfosuccinates such as sodium di(2-ethylhexyl)sulfosuccinate; sorbitol esters such as sorbitol oleate; quaternary amines such as lauryl trimethyl ammonium chloride; polyethylene glycol esters of fatty acids such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono- and dialkyl phosphate esters.

[0112] Other adjuvants commonly utilized in agricultural compositions include crystallization inhibitors, viscosity modifiers, suspending agents, spray size regulators, pigments, antioxidants, foaming agents, defoamers, light blocking agents, compatibilizers, antifoaming agents, sequestering agents, neutralizing and buffering agents, corrosion inhibitors, dyes, odorants, spreading agents, penetration aids, trace elements, emollients, lubricants and adhesives.

[0113] In addition, other biocidal active ingredients or compositions may be combined with the compositions of the present invention, used in the methods of the present invention, and applied simultaneously or sequentially with the compositions of the present invention. When applied simultaneously, these additional active ingredients may be formulated together with the compositions of the present invention or may be mixed together, for example, in a spray tank. These additional biocidal active ingredients may be fungicides, herbicides, insecticides, bactericides, acaricides, nematicides and / or plant growth regulators.

[0114] The pesticides referred to herein using their common names are known, for example, from “The Pesticide Manual”, 15th Ed., British Crop Protection Council 2009.

[0115] In addition, the compositions of the present invention may also be applied together with one or more systemic acquired resistance inducers ("SAR" inducers). SAR inducers are known and are described, for example, in U.S. Patent No. 6,919,298, and include, for example, salicylates and the commercially available SAR inducer acibenzolar-S-methyl.

[0116] The compounds of formula (I) are usually used in the form of agrochemical compositions and can be applied to the crop areas or plants to be treated simultaneously or sequentially with further compounds. These further compounds can be, for example, fertilizers or trace element donors or other preparations that influence plant growth. They can also be selective or non-selective herbicides, as well as insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, if desired with further carriers, surfactants or application-promoting adjuvants customarily used in the field of formulations.

[0117] The compounds of formula (I) may be used in the form of a (fungicidal) composition for the control or protection against phytopathogenic microorganisms, comprising as active ingredient at least one compound of formula (I) or at least one preferred individual compound as defined herein, in free form or in the form of an agrochemically usable salt, and at least one of the adjuvants mentioned above.

[0118] The present invention therefore provides a composition, preferably a fungicidal composition, comprising at least one compound of formula (I), an agriculturally acceptable carrier, and optionally an adjuvant. An agriculturally acceptable carrier is, for example, a carrier suitable for agricultural use. Agricultural carriers are well known in the art. Preferably, the composition may comprise, in addition to the compound of formula (I), at least one pesticidal active compound, for example an additional fungicidal active ingredient.

[0119] The compound of formula (I) may be the sole active ingredient in the composition or, where appropriate, may be mixed with one or more additional active ingredients, such as pesticides, fungicides, synergists, herbicides or plant growth regulators, which may in some cases result in unexpected synergistic activity.

[0120] Examples of suitable additional active ingredients are the following: acyl amino acid fungicides, aliphatic nitrogen fungicides, amide fungicides, anilide fungicides, antibiotic fungicides, aromatic fungicides, arsenic fungicides, aryl phenyl ketone fungicides, benzamide fungicides, benzanilide fungicides, benzimidazole fungicides, benzothiazole fungicides, botanical fungicides, fungicides, bridged diphenyl fungicides, carbamate fungicides, carbanilate fungicides, conazole fungicides, copper fungicides, dicarboximide fungicides, dinitrophenol fungicides, dithiocarbamate fungicides, dithiolane fungicides, furamide fungicides, furanilide fungicides, hydrazide fungicides, imidazole fungicides, mercury fungicides, Morpholine fungicides and fungicides, organophosphate fungicides and fungicides, organotin fungicides and fungicides, oxathiin fungicides and fungicides, oxazole fungicides and fungicides, phenylsulfamide fungicides and fungicides, polysulfide fungicides and fungicides, pyrazole fungicides and fungicides, pyridine fungicides and fungicides, pyrimidine fungicides and fungicides, pyrrole fungicides and fungicides, quaternary ammonium fungicides and fungicides, quinoline fungicides and fungicides, quinone fungicides and fungicides, quinoxaline fungicides These include fungicides, strobilurin fungicides, sulfonanilide fungicides, thiadiazole fungicides, thiazole fungicides, thiazolidine fungicides, thiocarbamate fungicides, thiophene fungicides, triazine fungicides, triazole fungicides, triazolopyrimidine fungicides, urea fungicides, valinamide fungicides and zinc fungicides.

[0121] Specific examples of suitable additional active ingredients that may be selected include petroleum, 1,1-bis(4-chlorophenyl)-2-ethoxyethanol, 2,4-dichlorophenylbenzenesulfonate, 2-fluoro-N-methyl-N-1-naphthylacetamide, 4-chlorophenylphenylsulfone, acetoprole, aldoxicarb, amidithione, amidothioate, amiton, amiton hydrogen oxalate, amitraz, aramite, arsenic oxide, azobenzene, azotoate, benomyl, benoxafos, benzyl benzoate, Bixafen, Brofenvalerate, Bromocyclen, Bromophos, Bromopropylate, Buprofezin, Butocarboxim, Butoxycarboxim, Butylpyridaben, Calcium polysulfide, Camphorchlor, Carbanolate, Carbophenothione, Cymiazole, Quinomethionate, Chlorbenside, Chlordimeform, Chlordimeform hydrochloride, Chlorphenetole, Chlorphenson, Chlorphenesulfide, Chlorbenzilate, Chlormebuform, Chlormethionon, Chloroprene Ropirate, Chlorthiophos, Cinerin I, Cinerin II, Cinerin, Closantel, Coumaphos, Crotamiton, Crotoxifos, Cufraneb, Cyanthoate, DCPM, DDT, Demefion, Demefion-O, Demefion-S, Demeton-methyl, Demeton-O, Demeton-O-Methyl, Demeton-S, Demeton-S-Methyl, Demeton-S-Methyl Sulfone, Dichlofluanid, Dichlorvos, Diglifos, Dienochlor, Dimefox, Zynex, Zynex-Diclexin, Zynocyanide Pu-4, Dinocap-6, Dinoctone, Dinopentone, Dinosulfone, Dinotervone, Dioxathion, Diphenylsulfone, Disulfiram, DNOC, Dofenapine, Doramectin, Endothion, Eprinomectin, Ethoate-methyl, Etrimphos, Fenazaflor, Fenbutatin Oxide, Fenothiocarb, Fenpyrad, Fenpyroximate, Fenpyrazamine, Fenson, Fentrifanil, Flubenzimine, Flucycloxuron, Fluentil, Fluorobenside, FMC 1137, Formetanate, Formetanate Hydrochloride, Forparanate, Gamma-HCH, Gliosin, Halfrenprox, Hexadecylcyclopropanecarboxylate, Isocarbophos,Jasmolin I, Jasmolin II, Iodofenphos, Lindane, Malonoben, Mecarbam, Mesfolan, Mesulfen, Methacrifos, Methyl bromide, Metolcarb, Mexacarbate, Milbemycin oxime, Mipafox, Monocrotophos, Morphothion, Moxidectin, Naled, 4-Chloro-2-(2-chloro-2-methyl-propyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one, Nifluridide, Nikkomycin, Nitrilacarb, Nitrilacarb 1:1 zinc chloride complex, Omethoate, Oxydepropionate s, oxydisulfoton, pp'-DDT, parathion, permethrin, fencapton, phosalone, phospholane, phosphamidon, polychloroterpenes, polynactin, proclonol, promacyl, propoxur, prothidathion, protoate, pyrethrin I, pyrethrin II, pyrethrins, pyridaphenthion, pyrimitate, quinalphos, quinthiophos, R-1492, phosglycine, rotenone, shladan, cebufos, selamectin, sofamide, SSI-121, sulfiram, sulfuramide, sulfotep, sulfur, diflovidazin, tau- Fluvalinate, TEPP, Terbam, Tetradifon, Tetrasulf, Thiafenox, Thiocarboxim, Thiofanox, Thiometon, Thioquinox, Thuringensin, Triamiphos, Triaten, Triazophos, Triazuron, Trifenophos, Trinactin, Vamidothion, Vaniliprole, Bethoxazin, Copper dioctanoate, Copper sulfate, Sibutrin, Dichlorn, Dichlorophen, Endothal, Fentin, Hydrated lime, Nabam, Quinoclamine, Quinonamide, Simazine, Triphenyltin acetate, Triphenyltin hydroxide, Curfomate, Pipet radin, thiophanate, chloralose, fenthion, pyridin-4-amine, strychnine, 1-hydroxy-1H-pyridine-2-thione, 4-(quinoxalin-2-ylamino)benzenesulfonamide, 8-hydroxyquinoline sulfate, bronopol, copper hydroxide, cresol, dipyrithione, dodysin, phenaminosulf, formaldehyde, hydralgafen, kasugamycin, kasugamycin hydrochloride hydrate, nickel bis(dimethyldithiocarbamate), nitropyrine, octhilinone, oxolinic acid, oxytetracycline,Potassium hydroxyquinoline sulfate, probenazole, streptomycin, streptomycin sesquisulfate, tecloftalam, thiomersal, Adoxophyes orana GV, Agrobacterium radiobacter, Amblyseius spp., Anagrapha falcifera NPV, Anagrus atomus, Aphelinus abdominalis, Aphidius colemani, Aphidoletes aphidimyza, Autographa californica NPV, Bacillus sphaericus Neide, Beauveria bronniathii brongniartii, Chrysoperla carnea, Cryptolaemus montrouzieri, Cydia pomonella GV, Dacnusa sibirica, Diglyphus isaea, Encarsia formosa, Eretmocerus eremicus, Heterorhabditis bacteriophora and H. megidis, Hippodamia convergens, Leptomastix dactylopii dactylopii, Macrolophus caliginosus, Mamestra brassicae NPV, Metaphycus helvolus,Metarhizium anisopliae var. acridum, Metarhizium anisopliae var. anisopliae, Neodiprion sertifer NPV and N. lecontei NPV, Orius spp., Paecilomyces fumosoroseus, Phytoseiulus persimilis, Steinernema bibionis, Steinernema carpocapsae, Steinernema feltiae, Steinernema glaseri, Steinernema riobrave, Steinernema riobrave, Steinernema riobravis, Steinernema scapterisci, Steinernema spp., Trichogramma spp., Typhlodromus occidentalis, Verticillium lecanii), afolate, bisazir, busulfan, dimatif, hemel, hempa, metepa, methiotepa, methyl afolate, molzide, penfluron, tepa, thiohempa, thiotepa, toretamine, uredepa, (E)-tridec-4-en-1-yl acetate with (E)-dec-5-en-1-yl acetate, (E)-6-methylhept-2-en-4-ol, (E)-tridec-4-en-1-yl acetate with (E)-dec-5-en-1-yl acetate, (E)-tridec-5-en-1-yl acetate with (E)-6-methylhept-2-en-4-ol, (E)-tridec-5-en-1-yl acetate with (E)-tridec-5-en-1-yl acetate ..., (E)-tridec-5-en-1-yl acetate, ( E,Z)-Tetradeca-4,10-dien-1-yl acetate, (Z)-dodec-7-en-1-yl acetate, (Z)-hexadec-11-enal, (Z)-hexadec-11-en-1-yl acetate, (Z)-hexadec-13-en-11-yn-1-yl acetate, (Z)-icos-13-en-10-one, (Z)-tetradec-7-en-1-al, (Z)-tetradec-9-en-1-ol,(Z)-Tetradeca-9-en-1-yl acetate, (7E,9Z)-dodeca-7,9-dien-1-yl acetate, (9Z,11E)-tetradeca-9,11-dien-1-yl acetate, (9Z,12E)-tetradeca-9,12-dien-1-yl acetate, 14-methyloctadec-1-ene, 4-methylnonan-5-ol α-multistriatin with 4-methylnonan-5-one, brevicomin, codramon, cudramon, disparlure, dodeca-8-en-1-yl acetate, 14-methyloctadec-1-ene ... Lure Acetate, Dodec-9-en-1-yl Acetate, Dodec-8,10-dien-1-yl Acetate, Dominical Lure, Ethyl 4-Methyloctanoate, Eugenol, Frontalin, Grand Lure, Grand Lure I, Grand Lure II, Grand Lure III, Grand Lure IV, Hexal Lure, Ipsdienol, Ipsenol, Japonyl Lure, Lineatin, Little Lure, Loop Lure, Medi Lure, Mega Atomic Acid, Methyl Eugenol, Muscal Lure, Octadeca-2,13-dien-1 -yl acetate, octadeca-3,13-dien-1-yl acetate, olflour, orictalure, ostramon, sigluer, sordidin sulcatol, tetradec-11-en-1-yl acetate, trimedlure, trimedlure A, trimedlure B1, trimedlure B2, trimedlure C, trunc-call, 2-(octylthio)ethanol, butopyronoxyl, butoxy(polypropylene glycol), dibutyl adipate, dibutyl phthalate, dibutyl succinate, diethyl thionate amide, dimethylcarbate, dimethylphthalate, ethyl hexanediol, hexamide, methoxine-butyl, methyl neodecaneamide, oxamate, picaridin, 1-dichloro-1-nitroethane, 1,1-dichloro-2,2-bis(4-ethylphenyl)ethane, 1,2-dichloropropane with 1,3-dichloropropene, 1-bromo-2-chloroethane, 2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate, 2,2-dichlorovinyl 2-ethylsulfinylethyl methyl phosphate, 2-(1,3-dithiolan-2-yl)phenyl dimethylcarbamate, 2-(2-butoxyethoxy)ethyl thiocyanate,2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenylmethylcarbamate, 2-(4-chloro-3,5-xylyloxy)ethanol, 2-chlorovinyl diethyl phosphate, 2-imidazolidone, 2-isovalerindan-1,3-dione, 2-methyl(prop-2-ynyl)aminophenylmethylcarbamate, 2-thiocyanate ethyl laurate, 3-bromo-1-chloroprop-1-ene, 3-methyl-1-phenylpyrazol-5-yldimethylcarbamate Bamate, 4-methyl(prop-2-ynyl)amino-3,5-xylylmethylcarbamate, 5,5-dimethyl-3-oxocyclohex-1-enyldimethylcarbamate, acetione, acrylonitrile, aldrin, allosamidin, alixiarb, alpha-ecdysone, aluminum phosphide, aminocarb, anabasine, atidathione, azamethiphos, Bacillus thuringiensis delta endotoxin deltaendotoxins), barium hexafluorosilicate, barium polysulfide, bartholin, Bayer 22 / 190, Bayer 22408, beta-cyfluthrin, beta-cypermethrin, bioethanomethrin, bioethanomethrin, bis(2-chloroethyl)ether, borax, bromfenbufos, bromo-DDT, bufencarb, butacarb, butathiophos, butonate, calcium arsenate, calcium cyanide, carbon disulfide, carbon tetrachloride, cartap hydrochloride, sebazine, chlorbicyclen, chlordane, chlordecone, chloroform, chloropicrin, chlorphoxime, chlorprazophos, cis-resmetry , simetryn, clocitryn, copper acetoarsenite, copper arsenate, copper oleate, kumitoate, acrolite, CS708, cyanofenphos, cyanophos, ciclethrin, cithioate, d-tetramethrin, DAEP, dazomet, decarbofuran, diamidaphos, dicapton, diclofenthion, dicresyl, dicyclanil, dieldrin, diethyl 5-methylpyrazol-3-yl phosphate, dirol, dimefluthrin, dimethane, dimethryn, dimethylvinphos, dimethyllan, dinoprop, dinosam, dinoseb, diofenolan, dioxabenzophos, dicyclophos, DSP, ecdysterone, EI1642,EMPC, EPBP, ethaphos, ethiofencarb, ethyl formate, ethylene dibromide, ethylene dichloride, ethylene oxide, EXD, fenchlorphos, fenetacarb, fenitrothion, fenoxacrim, fenpyritrin, fenthion ethyl, flucofuron, fosmetiran, fospirate, fostietan, furathiocarb, fretrin, guazatine, guazatine acetate, sodium tetrathiocarbonate, half-fenprox, HCH, HEOD, heptachlor, heterophos, HHDN, hydrogen cyanide , Hikincarb, IPSP, Isofunophos, Isobenzane, Isodrin, Isofenphos, Isoprothiolane, Isoxathion, Juvenile hormone I, Juvenile hormone II, Juvenile hormone III, Kereban, Kinoprene, Lead arsenate, Leptophos, Lilimphos, Ritidathion, m-Cumenylmethylcarbamate, Magnesium phosphide, Magidox, Mecarfone, Menazone, Mercurous chloride, Mesulfenphos, Metam, Meta-potassium, Meta-sodium, Methanesulfonyl fluoride, Metoclotophos, Methoprene, Methotrin, Methoxychlor, Methyl isothiocyanate , methyl chloroform, methylene chloride, methoxadiazone, mirex, naphthalophos, naphthalene, NC-170, nicotine, nicotine sulfate, nithiazine, nornicotine, O-5-dichloro-4-iodophenyl O-ethyl phosphonothioate, O,O-diethyl O-4-methyl-2-oxo-2H-chromen-7-yl phosphorothioate, O,O-diethyl O-6-methyl-2-propylpyrimidin-4-yl phosphorothioate, O,O,O',O'-tetrapropyl dithiopyrophosphate, oleic acid, paradichlorobenzene, parathion- Methyl, pentachlorophenol, pentachlorophenyl laurate, PH60-38, fenkapton, phosniclor, phosphine, phoxim-methyl, pyrimetaphos, polychlorodicyclopentadiene isomers, potassium arsenite, potassium thiocyanate, precocene I, precocene II, precocene III, primidophos, profluthrin, promecarb, prothiophos, pyrazophos, pyresmethrin, cassia, quinofos-methyl, quinothion, rafoxanide, resmethrin, rotenone, cadethrin, ryania, ryanodine, sabadilla), shradan,Cebufos, SI-0009, thiapronil, sodium arsenite, sodium cyanide, sodium fluoride, sodium hexafluorosilicate, sodium pentachlorophenoxide, sodium selenate, sodium thiocyanate, sulcofuron, sulcofuron sodium, sulfuryl fluoride, sulprofos, tar oil, tajincarb, TDE, tebupirimfos, temephos, telalethrin, tetrachloroethane, cyclofos, thiocyclam, thiocyclam hydrogen oxalate, thionazine, thiosultap, thiosultap-sodium, tralomethrin, transpermethrin, triazamate, trichloromethaphos-3, trichloronate, trimethacarb, tolprocarb, triclopyricarb, triplen, veratridine, veratrine, XMC, zetamethrin, zinc phosphate, zolaprofos, and meperfluthrin, tet tetramethylfluthrin, bis(tributyltin) oxide, bromoacetamide, ferric phosphate, niclosamide-olamine, tributyltin oxide, pyrimorph, triphenmorph, 1,2-dibromo-3-chloropropane, 1,3-dichloropropene, 3,4-dichlorotetrahydrothiophene 1,1-dioxide, 3-(4-chlorophenyl)-5-methylrhodanine, 5-methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid, 6-isopentenylaminopurine, anicifluprine, benclothiaz, cytokinins, DCIP, furfural, isamidophos, kinetin, myrothecium verrucaria composition, tetrachlorothiophene, xylenols, zeatin, potassium ethylxanthine, acibenzolar, acibenzolar-S-methyl, Reynoutria sakarinensis (Reynoutria sachalinensis) extract, alpha-chlorohydrin, antu, barium carbonate, bisthiosemi, brodifacoum, bromadiolone, bromethalin, chlorophacinone, cholecalciferol, coumachlor, coumafuryl, coumatetralyl, crimidine, difenacoum, difethialone, diphacinone, ergocalciferol, flocoumafen, fluoroacetamide, flupropazine, flupropazine hydrochloride, norbormide, phosacetin, phosphorus, pindone, pyrinuron, sciriloside, sodium fluoroacetate, thallium sulfate, warfarin,2-(2-butoxyethoxy)ethyl piperonylate, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone, farnesol with nerolidol, verbutin, MGK264, piperonyl butoxide, piperotal, propyl isomer, S421, sesamex, Sesamolin, sulfoxide, anthraquinone, copper naphthenate, copper oxychloride, dicyclopentadiene, thiram, zinc naphthenate, ziram, imanine, ribavirin, chlorinconazide, mercuric oxide, thiophanate methyl, azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, flamepyr, hexaconazole, imazalil, imibenconazole, ipconazole, metconazole, micro Butanil, paclobutrazol, pefurazoate, penconazole, prothioconazole, pyrifenox, prochloraz, propiconazole, pyrisoxazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triflumizole, triticonazole, ancymidol, fenarimol, nuarimol, bupirimate, dimethirimol, ethirimol, dodemorph, fenpropidin, fenpropimorph, spiroxamine, tridemorph, cyprodinil, mepanipyrim, pyrimethanil, fenpiclonil, Fludioxonil, benalaxyl, furalaxyl, metalaxyl, R-metalaxyl, ofurase, oxadixyl, carbendazim, debacarb, fuberidazole, thiabendazole, chlozolinate, diclozolin, mycrozolin, procymidone, vinclozolin, boscalid, carboxin, fenfuram, flutolanil, mepronil, oxycarboxin, penthiopyrad, thifluzamide, dodine, iminoctadine, azoxystrobin, dimoxystrobin, enestrobulin, phenaminestrobin, flufenoxystrobin, fluoxetine Sastrobin, kresoxim-methyl, metominostrobin, trifloxystrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, ferbam, mancozeb, maneb, metiram, propineb, zineb, captafol, captan, fluoroimide, folpet, tolylfluanid, boldeax mixture, copper oxide, mancopper, oxine copper, nitrothalisopropyl, edifenphos, iprobenfos, phosdifen, tolclofos-methyl, anilazine, benthiavalicarb,Blasticidin-S, chloroneb, chlorothalonil, cyflufenamid, cymoxanil, cyclobutrifluram, diclocymet, diclomedine, dicloran, diethofencarb, dimethomorph, flumorph, dithianon, ethaboxam, etridiazole, famoxadone, fenamidone, fenoxanil, ferimzone, fluazinam, flumethylsulfolim, fluopicolide, fluoxythioconazole, fluoxetine ... Lusulfamide, fluxapyroxad, fenhexamid, fosetyl aluminum, hymexazole, iprovalicarb, cyanofamide, methasulfocarb, metrafenone, pencycuron, phthalide, polyoxin, propamocarb, pyribencarb, proquinazid, pyroquilon, pyriophenone, quinoxyfen, quintozene, tiadinil, triazoxide, tricyclazole, triforine, validamycin, Valifenalate, Zoxamide, Mandipropamide, Fluveneram, Isopyrazam, Sedaxane, Benzovindiflupyr, Pydiflumetofen, 3-Difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3',4',5'-trifluoro-biphenyl-2-yl)-amide, Isoflucipram, Isotianil, Dipimethitrone, 6-Ethyl-5,7-dioxo-pyrrolo[4,5][1,4]dithiino[1,2-c]isothiazole-3-carbonitrile, 2-(Difluoromethyl)-N-[3-ethyl-1,1-dimethyl (R)-3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylidan-4-yl]pyrazole-4-carboxamide, 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine, 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl) -1,3-Dimethyl-1H-pyrazol-5-amine, fluindapyr, qmethoxystrobin (jiaxiangjunzhi) lvbenmixianan, diclobenthiazox, mandestrubin, 3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1-yl)quinolone, 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phenyl]propan-2-ol, oxathiapiproline, tert-butyl N-[6-[[[(1-methyltetrahydrofuran) 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide, N'-(2,5-dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine, N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-Dimethyl-phenyl]-N-ethyl-N-methyl-formamidine, [2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]thiazol-4-yl]-4,5-dihydroisoxazol-5-yl]-3-chloro-phenyl]methanesulfonate, but-3-ynyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate, methyl N-[[5-[4-(2,4- dimethylphenyl)triazol-2-yl]-2-methyl-phenyl]methyl]carbamate, 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine, pyridaclomethyl, 3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide, 1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one, 1-methyl-4-[3- Methyl-2-[[2-methyl-4-(3,4,5-trimethylpyrazol-1-yl)phenoxy]methyl]phenyl]tetrazol-5-one, aminopyrifen, amethoctrazine, amisulbrom, penflufen, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, florylpicoxamide, fenpicoxamide, tebufloquine, ipflufenoquine, quinofumelin, isofetamide, N-[2-[2,4-dichloro- phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide, N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide, benzothiostrobin, phenamacryl, 5-amino-1,3,4-thiadiazole-2-thiol zinc salt (2:1), fluopyram, flutianil, fluopimomide, pyrapropoin, picarbutorazox, 2-(difluoromethyl)-N-(3-ethyl-1,1-Dimethyl-indan-4-yl)pyridine-3-carboxamide, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, Methyltetraprole, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide xamide, α-(1,1-dimethylethyl)-α-[4'-(trifluoromethoxy)[1,1'-biphenyl]-4-yl]-5-pyrimidinethanol, fluoxapiproline, enoxastrobin, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-sulfanyl-1,2,4-Triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, trinexapac, comoxystrobin, zhongshengmycin, copper thiodiazole, zinc thiazole, amethotractin, iprodione, sebocthylamine, N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-chloro-2-methyl-6-(1-methyl-2 -propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidine (these compounds can be prepared from the method described in WO 2015 / 155075); N'-[5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine (these compounds can be prepared from the method described in IPCOM000249876D); N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenyl-ethyl)phenyl]-N-methyl-formamidine, N'-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-methoxy-2-methyl-phenyl]-N-isopropyl-N-methyl-formamidine (these compounds can be prepared according to the methods described in WO 2018 / 228896); N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)oxetan-2-yl]phenyl]-N-methyl-formamidine, N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methyl-formamidine (these compounds can be prepared according to the methods described in WO 2019 / 110427); N-[ (1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide, N-[(1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide, N-[(1R)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide, N-[(1S)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide, 8-fluoro-N-[(1R)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide, 8-fluoro-N-[(1S)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide, N-((1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide, N-((1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide (these compounds can be prepared according to the method described in WO 2017 / 153380); 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,5-trifluoro- 3,3-Dimethyl-isoquinoline, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,6-trifluoro-3,3-dimethyl-isoquinoline, 4,4-difluoro-3,3-dimethyl-1-(6-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline, 4,4-difluoro-3,3-dimethyl-1-(7-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline, 1-(6-chloro-7-methyl-pyrazolo 1-(4,5-dimethylbenzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline, 1-(4,5-dimethylbenzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline, 6-chloro-4,4-di ...1-(4,5-dimethylbenzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline, 1-(4,5-dimethylbenzimidazol-1-yl) Fluoro-3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline, 4,4-difluoro-1-(5-fluoro-4-methyl-benzimidazol-1-yl)-3,3-dimethyl-isoquinoline, 3-(4,4-difluoro-3,3-dimethyl-1-isoquinolyl)-7,8-dihydro-6H-cyclopenta[e]benzimidazole (these compounds can be prepared according to the method described in WO 2016 / 156085);N-Methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, 1-Methoxy-3-methyl-1-[[4-[5-(trifluoromethyl) 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, -yl]phenyl]methyl]-1,2,4-triazol-3-amine (these compounds can be prepared from the methods described in WO 2017 / 055473, WO 2017 / 055469, WO 2017 / 093348 and WO 2017 / 118689); 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol (this compound can be prepared from the methods described in WO 2017 / 029179);2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol (this compound can be prepared from the method described in WO 2017 / 029179); 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile (this compound can be prepared from the method described in WO 2016 / 156290); 3-[2-(1-chlorocyclopropyl)-3-(3-chloro (4-phenoxyphenyl)methyl 2-amino-6-methyl-pyridine-3-carboxylate (this compound can be prepared from the method described in WO 2014 / 006945); 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetrone (this compound can be prepared from the method described in WO 201 N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide (which can be prepared from the method described in WO 2018 / 138281); N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide; (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (this compound can be prepared from the method described in WO 2018 / 153707); N'- (2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine; N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine (this compound can be prepared from the method described in WO 2016 / 202742); 2-(difluoromethyl)-N-[(3S)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (this compound can be prepared from the method described in WO 2014 / 095675);(5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone, (3-methylisoxazol-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone (these compounds can be prepared from the method described in WO 2017 / 220485); 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide (this compound can be prepared from the method described in WO 2018 / 065414); ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate (this compound can be prepared from the method described in WO 2018 / 158365). can be prepared from the method described in WO 2018 / 202428), fluoxapiproline, enoxastrobin, trinexapac, cumoxystrobin; 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide, N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, N-[N-methoxy-C-methyl-carbonimidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide (these compounds can be prepared from the method described in WO 2018 / 202428), fluoxapiproline, enoxastrobin, trinexapac, cumoxystrobin.

[0122] N-Methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide, N,2-Dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, N-Ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3 -yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4- oxadiazol-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1, 2,4-Oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-1,2,4-triazol-3-amine. The compounds of this paragraph can be prepared from the methods described in WO 2017 / 055473, WO 2017 / 055469, WO 2017 / 093348 and WO 2017 / 118689.

[0123] 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol (this compound can be prepared from the method described in WO 2017 / 029179), 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol (this compound can be prepared from the method described in WO 2017 / 029179). ), 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile (this compound can be prepared from the methods described in WO 2016 / 156290), 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile (this compound can be prepared from the methods described in WO 2016 / 156290).

[0124] (4-phenoxyphenyl)methyl 2-amino-6-methyl-pyridine-3-carboxylate (this compound can be prepared by the method described in WO 2014 / 006945), 2,6-dimethyl-1H,5H-[1,4]dithino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetrone (this compound can be prepared by the method described in WO 2011 / 138281). (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (This compound can be prepared from the method described in WO 2018 / 153707), N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine, N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine (This compound can be prepared from the method described in WO 2016 / 202742), 2-(difluoromethyl)-N-[(3S)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (This compound can be prepared from the method described in WO 2014 / 095675), zhongshengmycin, copper thiodiazole, zinc thiazole, amethotractin, iprodione, cyclobutrifluram, fulveneteram, anicifluprine.

[0125] N-[(1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide, N-[(1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide, N-[(1R)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide, N-[( 1S)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide, 8-fluoro-N-[(1R)-1-[( 3-Fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide, 8-Fluoro-N-[(1S)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]- N-((1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide, N-((1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide (these compounds can be prepared according to the method described in WO 2017 / 153380).

[0126] 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,6-trifluoro-3,3-dimethyl-isoquinoline, 4,4-difluoro-3,3-dimethyl-1-(6-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline, 4,4-difluoro-3,3-dimethyl-1-(7-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline, 1-(6-chloro-7-methyl-pyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline (these compounds were prepared by the method described in WO 2017 / 025510). can be prepared from the methods described in WO 2016 / 156085), 1-(4,5-dimethylbenzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline, 1-(4,5-dimethylbenzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline, 6-chloro-4,4-difluoro-3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline, 4,4-difluoro-1-(5-fluoro-4-methyl-benzimidazol-1-yl)-3,3-dimethyl-isoquinoline, 3-(4,4-difluoro-3,3-dimethyl-1-isoquinolyl)-7,8-dihydro-6H-cyclopenta[e]benzimidazole (these compounds can be prepared from the methods described in WO 2016 / 156085).

[0127] N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-chloro -2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidine (these compounds can be prepared according to the method described in WO 2015 / 155075); N'-[5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine; N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenyl-ethyl)phenyl]-N-methyl-formamidine, N'-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-methoxy-2-methyl-phenyl]-N-isopropyl-N-methyl-formamidine (these compounds can be prepared according to the method described in IPCOM000249876D); N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)oxetan-2-yl]phenyl]-N-methyl-formamidine, N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methyl-formamidine (these compounds can be prepared from the methods described in WO 2019 / 110427).

[0128] (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone, (3-methylisoxazol-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone (these compounds can be prepared from the methods described in WO 2017 / 220485); 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide (this compound can be prepared from the methods described in WO 2018 / 065414); Ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate (this compound can be prepared from the method described in WO 2018 / 158365); 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide, N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, benzamide, N-[N-methoxy-C-methyl-carbonimidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide (these compounds can be prepared from the methods described in WO 2018 / 202428); N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, [(1S,2S)-1-methyl-2-(o-tolyl)propyl](2S)-2-[(4-methoxy-3-propanoyloxy-pyridine-2-carbonyl)amino]propanoate, seboxylamine, chlorincon azide, flumethylsulfolim, fluoxythioconazole.

[0129] The following mixtures of compounds of formula (I) with active ingredients are preferred: The abbreviation "TX" means one compound selected from the group consisting of the compounds shown in Tables A-1 to A-26 or B-1 to B-44 below, or the compounds shown in Tables T1 or T2 below. A compound selected from the group of substances consisting of: petroleum + TX, 1,1-bis(4-chlorophenyl)-2-ethoxyethanol + TX, 2,4-dichlorophenylbenzenesulfonate + TX, 2-fluoro-N-methyl-N-1-naphthylacetamide + TX, 4-chlorophenylphenylsulfone + TX, acetoprole + TX, aldoxicarb + TX, amidithione + TX, amidothioate + TX, amiton + TX, amiton hydrogen oxalate + TX, amitraz + TX, aramite + TX, arsenic oxide + TX, azobenzene + TX, azotoate + T X, benomyl + TX, benoxafos + TX, benzyl benzoate + TX, bixafen + TX, brofenvalerate + TX, bromocyclen + TX, bromophos + TX, bromopropylate + TX, buprofezin + TX, butocarboxim + TX, butoxycarboxim + TX, butylpyridaben + TX, calcium polysulfide + TX, camphorchlor + TX, carbanolate + TX, carbophenothione + TX, cymiazole + TX, chinomethionate + TX, chlorbenside + TX, chlordimeform + TX, chlordimeform hydrochloride + T X, Chlorphenetole + TX, Chlorfenson + TX, Chlorphenesulfide + TX, Chlorobenzilate + TX, Chlormebform + TX, Chlormethiuron + TX, Chloropropylate + TX, Chlorthiophos + TX, Cineline I + TX, Cineline II + TX, Cineline + TX, Closantel + TX, Coumaphos + TX, Crotamiton + TX, Crotoxifos + TX, Cyufuraneb + ​​TX, Cyanthoate + TX, DCPM + TX, DDT + TX, Demefion + TX, Demefion-O + TX, Demefion-S + TX, Demeton-methyl + TX, Demeton-O+TX, Demeton-O-methyl+TX, Demeton-S+TX, Demeton-S-methyl+TX, Demeton-S-methylsulfone+TX, Dichlofluanid+TX, Dichlorvos+TX, Diglifos+TX, Dienochlor+TX, Dimefox+TX, Zinex+TX, Zinex-diclexin+TX, Dinocap-4+TX, Dinocap-6+TX, Dinocton+TX, Dinopenton+TX, Dinosulfone+TX, Dinotervone+TX, Dioxathion+TX, Diphenylsulfone+TX, Disulfiram+TX, DNOC+TX,Dofenapine + TX, Doramectin + TX, Endothion + TX, Eprinomectin + TX, Ethoate methyl + TX, Etrimphos + TX, Fenazaflor + TX, Fenbutatin oxide + TX, Fenothiocarb + TX, Fenpyrad + TX, Fenpyroximate + TX, Fenpyrazamine + TX, Fenson + TX, Fentrifanil + TX, Flubenzimine + TX, Flucycloxuron + TX, Fluentil + TX, Fluorobenside + TX, FMC1137 + TX, Formetanate + TX, Formetanate hydrochloride + TX, Forparane ate+TX, gamma-HCH+TX, gliodin+TX, halfrenprox+TX, hexadecylcyclopropanecarboxylate+TX, isocarbophos+TX, jasmolin I+TX, jasmolin II+TX, iodofenphos+TX, lindane+TX, malonoven+TX, mecarbam+TX, mesfolan+TX, mesulfen+TX, methacrifos+TX, methyl bromide+TX, metolcarb+TX, mexacarbate+TX, milbemycin oxime+TX, mipafox+TX, monocrotophos+TX, morphothion+TX, moxidectin +TX, naled+TX, 4-chloro-2-(2-chloro-2-methyl-propyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one+TX, nifluridide+TX, nikkomycin+TX, nitrilacarb+TX, nitrilacarb 1:1 zinc chloride complex+TX, omethoate+TX, oxydeprophos+TX, oxydisulfoton+TX, pp'-DDT+TX, parathion+TX, permethrin+TX, fencaptone+TX, phosalone+TX, phospholane+TX, phosphamidon+TX, polychloroterpenes+TX, polynaphthalene+TX Chin+TX, Proclonol+TX, Promacyl+TX, Propoxur+TX, Protidathion+TX, Protoate+TX, Pyrethrin I+TX, Pyrethrin II+TX, Pyrethrin+TX, Pyridaphenthion+TX, Pirimitate+TX, Quinalphos+TX, Quinthiophos+TX, R-1492+TX, Phosglycine+TX, Rotenone+TX, Shladan+TX, Cebufos+TX, Selamectin+TX, Sofamide+TX, SSI-121+TX, Sulfiram+TX, Sulfuramide+TX, Sulfotep+TX, Sulfur+TX, Diflovidazin+TX,Tau-fluvalinate+TX, TEPP+TX, Terbam+TX, Tetradifon+TX, Tetrasul+TX, Thiafenox+TX, Thiocarboxim+TX, Thiofanox+TX, Thiometon+TX, Thioquinox+TX, Thuringensin+TX, Triamiphos+TX, Triaratin+TX, Triazophos+TX, Triazuron+TX, Trifenophos+TX, Trinactin+TX, Vamidothion+TX, Vaniliprole+TX, Bethoxazin +TX, copper dioctanoate +TX, copper sulfate +TX, sibutrin +TX, dichloren +TX, dichlorophen +TX, endothal +TX, fentin +TX, hydrated lime +TX, nabam +TX, quinoclamine +TX, quinonamide +TX, simazine +TX, triphenyltin acetate +TX, triphenyltin hydroxide +TX, crufomate +TX, piperazine +TX, thiophanate +TX, chloralose +TX, fenthion +TX, pyridin-4-amine +TX, Strychnine + TX, 1-hydroxy-1H-pyridine-2-thione + TX, 4-(quinoxalin-2-ylamino)benzenesulfonamide + TX, 8-hydroxyquinoline sulfate + TX, bronopol + TX, copper hydroxide + TX, cresol + TX, dipyrithione + TX, dojisin + TX, phenaminosulf + TX, formaldehyde + TX, hydralgafen + TX, kasugamycin + TX, kasugamycin hydrochloride hydrate + TX, nickel bi (dimethyldithiocarbamate) + TX, nitropyrine + TX, octhilinone + TX, oxolinic acid + TX, oxytetracycline + TX, potassium hydroxyquinoline sulfate + TX, probenazole + TX, streptomycin + TX, streptomycin sesquisulfate + TX, tecloftalam + TX, thiomersal + TX, Adoxophyes orana GV + TX, Agrobacterium radiobacter + TX, Amblyseius species + TX, Anagrapha falcifera NPV + TX, Anagrus atomus + TX, Aphelinus abdominalis + TX,Aphidius colemani+TX, Aphidoletes aphidimyza+TX, Autographa californica NPV+TX, Bacillus sphaericus Neide+TX, Beauveria brongniartii+TX, Chrysoperla carnea+TX, Cryptolaemus montrouzieri+TX, Cydia pomonella GV+TX, Dacnusa sibirica+TX, Diglyphus isaea+TX, Encarsia formosa+TX formosa+TX, Eretmocerus eremicus+TX, Heterorhabditis bacteriophora and H.megidis+TX, Hippodamia convergens+TX, Leptomastix dactylopii+TX, Macrolophus caliginosus+TX, Mamestra brassicae NPV+TX, Metaphycus helvolus+TX, Metarhizium anisopliae var.acridum+TX, Metarhizium anisopliae var.anisopliae anisopliae var. anisopliae + TX, Neodiprion sertifer NPV and N. lecontei NPV + TX, Orius spp. + TX,Paecilomyces fumosoroseus+TX, Phytoseiulus persimilis+TX, Steinernema bibionis+TX, Steinernema carpocapsae+TX, Steinernema feltiae+TX, Steinernema glaseri+TX, Steinernema riobrave+TX, Steinernema riobravis+TX, Steinernema scapterisci+TX, Steinernema spp.+TX, Trichogramma spp.)+TX, Typhlodromus occidentalis+TX, Verticillium lecanii lecanii) + TX, afolate + TX, bisazil + TX, busulfan + TX, dimatif + TX, hemel + TX, hempa + TX, metepa + TX, methiotepa + TX, methyl afolate + TX, molzide + TX, penfluron + TX, tepa + TX, thiohempa + TX, thiotepa + TX, tretamine + TX, uredepa + TX, (E)-dec-5-en-1-yl acetate + TX with (E)-dec-5-en-1-ol, (E)-tridec-4-en-1-yl acetate + TX, (E)-6-methylhept-2-en-4-ol + TX, (E,Z)-tetradec-4,10-dien-1-yl acetate + TX, (Z)-dodec-7-en-1-yl acetate + TX, (Z)-hexadec-11-enal + TX, (Z)-hexadec-11-en-1-yl acetate + TX, (Z)-hexadec-13-en-11-yn-1-yl acetate + TX, (Z)-icos-13-en-10-one + TX, (Z)-tetradec-7-en-1-al + TX, (Z)-tetradec-9-en-1-ol + TX, (Z)-tetradec-9-en-1-yl acetate + TX, (7E,9Z)-dodeca-7,9-dien-1-yl acetate + TX, (9Z, 11E)-Tetradeca-9,11-dien-1-yl acetate + TX, (9Z,12E)-Tetradeca-9,12-dien-1-yl acetate + TX, 14-methyloctadec-1-ene + TX, 4-methylnonan-5-ol with 4-methylnonan-5-one, α-multistriatin + TX, brevicomin + TX, chordalure + TX, chordamon + TX, curar + TX, disparlure + TX, dodec-8-en-1-yl acetate + TX, dodec-9-en-1-yl acetate + TX, dodec-8 + TX, 10-dien-1-yl acetate + TX, dodec-8 + TX, Ile acetate + TX, Dominical lure + TX, Ethyl 4-methyloctanoate + TX, Eugenol + TX, Frontalin + TX, Grand Lure + TX, Grand Lure I + TX, Grand Lure II + TX, Grand Lure III + TX, Grand Lure IV + TX, Hexal lure + TX, Ipsdienol + TX, Ipsenol + TX, Japonyl lure + TX, Lineatin + TX, Little lure + TX, Loop lure + TX, Medi lure + TX, Megaatomic acid + TX, Methyl eugenol + TX, Muscal lure + TX, Octadeca-2,13-di 1-enyl acetate + TX, octadeca-3,13-dien-1-yl acetate + TX, Olfraluer + TX, Orictalluer + TX, Ostramon + TX, Sigluer + TX, Soldidin sulcatol + TX, Tetradec-11-en-1-yl acetate + TX, Trimedrure + TX, Trimedrure A + TX, Trimedrure B1 + TX, Trimedrure B2 + TX, Trimedrure C + TX, trunc-call + TX, 2-(octylthio)ethanol + TX, Butopyronoxyl + TX, Butoxy(polypropylene glycol) + TX,Dibutyl adipate + TX, dibutyl phthalate + TX, dibutyl succinate + TX, diethyl toluamide + TX, dimethylcarbate + TX, dimethyl phthalate + TX, ethyl hexanediol + TX, hexamide + TX, methoquin-butyl + TX, methyl neodecane amide + TX, oxamate + TX, picaridin + TX, 1-dichloro-1-nitroethane + TX, 1,1-dichloro-2,2-bis(4-ethylphenyl)ethane + TX, 1,2-dichloropropane with 1,3-dichloropropene + TX, 1-bromo-2-chloroethane + TX, 2,2,2-trichloro-1-(3,4-dichlorophenyl)ethyl acetate + TX, 2,2-dichlorovinyl 2-ethylsulfinylethyl methyl phosphate + TX, 2-(1,3-dithiolan-2-yl)phenyl dimethyl carbamate + TX, 2-(2-butoxyethoxy)ethyl thiocyanate + TX, 2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methyl carbamate + TX, 2-(4-chloro-3,5-xylyloxy)ethanol + TX, 2-chlorovinyl diethyl phosphate + TX, 2-imidazoline Don + TX, 2-isovalerylindan-1,3-dione + TX, 2-methyl(prop-2-ynyl)aminophenyl methyl carbamate + TX, 2-thiocyanatoethyl laurate + TX, 3-bromo-1-chloroprop-1-ene + TX, 3-methyl-1-phenylpyrazol-5-yl dimethyl carbamate + TX, 4-methyl(prop-2-ynyl)amino-3,5-xylyl methyl carbamate + TX, 5,5-dimethyl-3-oxocyclohex-1-enyl dimethyl carbamate + TX, acetone + TX, acrylonitrile + TX, Aldrin+TX, Allosamidin+TX, Allylxycarb+TX, Alpha-ecdysone+TX, Aluminum phosphide+TX, Aminocarb+TX, Anabasine+TX, Azidathione+TX, Azamethiphos+TX, Bacillus thuringiensis delta endotoxin+TX, Barium hexafluorosilicate+TX, Polysulfide+TX, Bartholin+TX, Bayer22 / 190+TX, Bayer22408+TX, Beta-cyfluthrin+TX, Beta-cypermethrin+TX, Bioethanomethrin+TX, Biopermethrin+TX,Bis(2-chloroethyl)ether+TX, Borax+TX, Bromfeninfuphos+TX, Bromo-DDT+TX, Bufencarb+TX, Butacarb+TX, Butathiophos+TX, Butonate+TX, Calcium arsenate+TX, Calcium cyanide+TX, Carbon disulfide+TX, Carbon tetrachloride+TX, Cartap hydrochloride+TX, Cevadine+TX, Chlorbicyclen+TX, Chlordane+TX, Chlordecone+TX, Chloroform+TX, Chloropicrin+TX, Chlorphoxim+TX, Chlorprazophos+TX, Cis-Resmethrin+TX, Simetry methionine+TX, clocitrin+TX, copper acetoanite+, copper arsenate+TX, copper oleate+TX, cumisoate+TX, cryolite+TX, CS708+TX, cyanofenphos+TX, cyanophos+TX, cicrethrin+TX, cithioate+TX, d-tetramethrin+TX, DAEP+TX, dazomet+TX, decarbofuran+TX, diamidaphos+TX, dikapton+TX, diclofenthion+TX, dicresyl+TX, dicyclanil+TX, dieldrin+TX, diethyl 5-methylpyrazol-3-yl phosphate+TX, dirol+TX, di Mefluthrin+TX, Dimethan+TX, Dimethryn+TX, Dimethylvinphos+TX, Dimethylan+TX, Dinoprop+TX, Zinam+TX, Dinoseb+TX, Diofenolan+TX, Dioxabenzophos+TX, Dicyclophos+TX, DSP+TX, Ecdysterone+TX, EI1642+TX, EMPC+TX, EPBP+TX, Ethaphos+TX, Ethiofencarb+TX, Ethyl formate+TX, Ethylene dibromide+TX, Ethylene dichloride+TX, Ethylene oxide+TX, EXD+TX, Fenchlorphos+TX, Fenetacarb+T X, Fenitrothion + TX, Fenoxacrim + TX, Fenpyritrin + TX, Fensulfothion + TX, Fenthion Ethyl + TX, Flucofuron + TX, Fosmisilan + TX, Hospirate + TX, Fostietan + TX, Furathiocarb + TX, Frethrin + TX, Guazatine + TX, Guazatine Acetate + TX, Sodium Tetrathiocarbonate + TX, Halfpenprox + TX, HCH + TX, HEOD + TX, Heptachlor + TX, Heterofos + TX, HHDN + TX, Hydrogen Cyanide + TX, Hikincarb + TX, IPSP + TX,Isazophos+TX, Isobenzan+TX, Isodrin+TX, Isofenphos+TX, Isorane+TX, Isoprothiolane+TX, Isoxathion+TX, Juvenile Hormone I+TX, Juvenile Hormone II+TX, Juvenile Hormone III+TX, Kelan+TX, Kinoprene+TX, Lead Arsenate+TX, Leptophos+TX, Silimphos+TX, Ritthion+TX, m-Cumenylmethylcarbamate+TX, Magnesium Phosphide+TX, Magidox+TX, Mecarfone+TX, Menazone+TX, Mercurous Chloride+TX, Mesulfenphos+TX, Metam+TX, Metakalium +TX, Methasodium +TX, Methanesulfonyl fluoride +TX, Metoclotophos +TX, Methoprene +TX, Methotrin +TX, Methoxychlor +TX, Methyl isothiocyanate +TX, Methyl chloroform +TX, Methylene chloride +TX, Methoxadiazone +TX, Mirex +TX, Naphthalophos +TX, Naphthalene +TX, NC-170 +TX, Nicotine +TX, Nicotine sulfate +TX, Nithiazine +TX, Nornicotine +TX, O-5-Dichloro-4-iodophenyl O-ethylphosphonothioate +TX, O,O-Diethyl O-4-methyl- 2-Oxo-2H-chromen-7-yl phosphorothioate + TX, O,O-Diethyl O-6-methyl-2-propylpyrimidin-4-yl phosphorothioate + TX, O,O,O',O'-Tetrapropyldithiopyrophosphate + TX, Oleic acid + TX, Paradichlorobenzene + TX, Parathion-methyl + TX, Pentachlorophenol + TX, Pentachlorophenyl laurate + TX, PH60-38 + TX, Fenkapton + TX, Phosniclor + TX, Phosphine + TX, Phoxim-methyl + TX, Pyrimetaphos + TX, Polychlorodisil Lopentadiene isomers + TX, potassium arsenite + TX, potassium thiocyanate + TX, precocene I + TX, precocene II + TX, precocene III + TX, primidophos + TX, profluthrin + TX, promecarb + TX, prothiophos + TX, pyrazophos + TX, pyresmethrin + TX, cassia + TX, quinafos-methyl + TX, quinothione + TX, rafoxanide + TX, resmethrin + TX, rotenone + TX, cadethrin + TX, ryania + TX, ryanodine + TX, sabadira) + TX, shradan + TX, cebufos + TX, SI-0009 + TX,Tiapronil+TX, Sodium arsenite+TX, Sodium cyanide+TX, Sodium fluoride+TX, Sodium hexafluorosilicate+TX, Sodium pentachlorophenoxide+TX, Sodium selenate+TX, Sodium thiocyanate+TX, Sulfuron+TX, Sulfuron-sodium+TX, Sulfuryl fluoride+TX, Sulprofos+TX, Tal oil+TX, Tajincarb+TX, TDE+TX, tebupirimfos+TX, temephos+TX, terallethrin+TX, tetrachloroethane+TX, cyclophos+TX, thiocyclam+TX, thiocyclam hydrogen oxalate+TX, thionazine+TX, thiosultap+TX, thiosultap-sodium+TX, tralomethrin+TX, transpermethrin+TX, triazamate+TX, trichloromethos-3+TX, trichloronate+TX, trimethacarb+TX, tolprocarb+TX, triclopiricarb+TX, triplen+TX, veratridine+TX, veratrine+TX, XMC+TX, zetamethrin+TX, zinc phosphate+TX, zolaprophos+TX, and meperfluthrin+TX, tetramethylfluthrin+TX, bis(tributyltin)oxide+TX, bromoacetamido oxalate + TX, ferric phosphate + TX, niclosamide-olamine + TX, tributyltin oxide + TX, pyrimorph + TX, triphenmorph + TX, 1,2-dibromo-3-chloropropane + TX, 1,3-dichloropropene + TX, 3,4-dichlorotetrahydrothiophene 1,1-dioxide + TX, 3-(4-chlorophenyl)-5-methylrhodanine + TX, 5-methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid + TX, 6-isopentenylaminopurine + TX, 2-fluoro-N-(3-methoxyphenyl)-9H-purin-6-amine + TX, benclothiaz + TX, cytokinin + TX, DCIP + TX, furfural + TX, isamidophos + TX, kinetin + TX, Myrothecium verrucaria verrucaria composition +TX, tetrachlorothiophene +TX, xylenol +TX, zeatin +TX, potassium ethylxanthine +TX, acibenzolar +TX, acibenzolar-S-methyl +TX, Reynoutria sachalinensis extract +TX, α-chlorohydrin +TX, antu +TX, barium carbonate +TX, bisthiosemi +TX, brodifacoum +TX, bromadiolone +TX, bromethalin +TX, chlorophacinone +TX, cholecalciferol +TX, coumachlor +TX, coumafuryl +TX, coumatetralyl +TX, crimidine +TX, difenacoum +TX, difethialone +TX, diphacinone +TX,Ergocalciferol +TX, flocoumafen +TX, fluoroacetamide +TX, flupropazine +TX, flupropazine hydrochloride +TX, norbormide +TX, fosacetim +TX, phosphorus +TX, pindone +TX, pyrinuron +TX, sciliroside +TX, sodium fluoroacetate +TX, thallium sulfate +TX, warfarin +TX, 2-(2-butoxyethoxy)ethyl piperonylate +TX, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone +TX, farnesol with nerolidol +TX, belbuchi methyl ketone +TX, MGK264 +TX, piperonyl butoxide +TX, piprotal +TX, propyl isomer +TX, S421 +TX, sesamex +TX, sesamolin +TX, sulfoxide +TX, anthraquinone +TX, copper naphthenate +TX, copper oxychloride +TX, dicyclopentadiene +TX, thiram +TX, zinc naphthenate +TX, ziram +TX, imanin +TX, ribavirin +TX, mercuric oxide +TX, thiophanate methyl +TX, azaconazole +TX, bitertanol +TX, bromoconazole +TX, cyproconazole +TX, difenoconazole ol+TX, diconazole+TX, epoxiconazole+TX, fenbuconazole+TX, fluquinconazole+TX, flusilazole+TX, flutriafol+TX, furametapyr+TX, hexaconazole+TX, imazalil+TX, imibenconazole+TX, ipconazole+TX, metconazole+TX, myclobutanyl+TX, paclobutrazol+TX, pefurazoate+TX, penconazole+TX, prothioconazole+TX, pyrifenox+TX, prochloraz+TX, propiconazole+TX, pyrisoxazole+TX , Simeconazole + TX, Tebuconazole + TX, Tetraconazole + TX, Triadimefon + TX, Triadimenol + TX, Triflumizole + TX, Triticonazole + TX, Ancymidol + TX, Fenarimol + TX, Nuarimol + TX, Bupirimate + TX, Dimethirimol + TX, Ethirimol + TX, Dodemorph + TX, Fenpropidin + TX, Fenpropimorph +, Spiroxamine + TX, Tridemorph + TX, Cyprodinil + TX, Mepanipyrim + TX, Pyrimethanil + TX, Fenpiclonil + TX, Fludioxonil + TX,Benalaxyl + TX, Furalaxyl + TX, Metalaxyl- + TX, Lametaxyl + TX, Ofrace + TX, Oxadixyl + TX, Carbendazim + TX, Debacarb + TX, Fuberidazole + TX, Thiabendazole + TX, Chlozolinate + TX, Diclozolin + TX, Myclozolin + TX, Procymidone + TX, Vinclozolin + TX, Boscalid + TX, Carboxin + TX, Fenfuram + TX, Flutolanil + TX, Mepronil + TX, Oxycarboxin + TX, Penthiopyrad +, Thifluzamide + TX, Dodine + TX, Iminoctazide strobin+TX, azoxystrobin+TX, dimoxystrobin+TX, enestrogen+TX, phenaminestrobin+TX, flufenoxystrobin+TX, fluoxastrobin+TX, kresoxim-methyl+TX, metominostrobin+TX, trifloxystrobin+TX, orysastrobin+TX, picoxystrobin+TX, pyraclostrobin+TX, pyrametostrobin+TX, pyraoxystrobin+TX, ferbam+TX, mancozeb+TX, maneb+TX, metiram+TX, propineb+TX, zineb+TX, captafor 1,2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17,18,19,19,20,21,22,23,24,25,26,27,28,29,30,31,32,29,33,34,35,36,37,38,39,40,41,42,43,44,45,50,51,52,53,54,55,56,57,58,60,61,72,73,74,75,59,62,76,77,78,79,80,81,94,82,95,96,97,98,99,99,100,110,120,130,140,150,160,170,180,190,191,192,193,194,195,196,201,202,203,204,205,206,211,221,230,241,252,261,272,282,30,31,32,33,34,35,46,47,50,51,62,73,74,75,52,76,77,78,99,99,100,110,120,130,140,150,160,171,192,193,204,205,206,211,221,230,241,252,261,272,282,30,31,32,33,34,35,46, , dicloran + TX, diethofencarb + TX, dimethomorph + TX, flumorph + TX, dithianon + TX, ethaboxam + TX, etridiazole + TX, famoxadone + TX, fenamidone + TX, fenoxanil + TX, ferimzone + TX, fluazinam + TX, fluopicolide + TX, flusulfamide + TX, fluxapyroxad + TX, fenhexamid + TX, fosetyl-aluminum + TX, hymexazole + TX, iprovalicarb + TX, cyazofamid + TX, methasulfocarb + TX, metrafenone + TX,Pencycuron+TX, Phthalide+TX, Polyoxin+TX, Propamocarb+TX, Pyribencarb+TX, Proquinazid+TX, Pyroquilon+TX, Pyriophenone+TX, Quinoxyfen+TX, Quintozene+TX, Tiadinil+TX, Triazoxide+TX, Tricyclazole+TX, Triforine+TX, Validamycin+TX, Valifenalate+TX, Zoxamide+TX, Mandipropamid + TX, Fluvenetam + TX, Isopyrazam + TX, Sedaxane + TX, Benzovindiflupyr + TX, Pydiflumetofen + TX, 3-Difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3',4',5'-trifluoro-biphenyl-2-yl)-amide + TX, Isoflucipram + TX, Isotianil + TX, Dipimethitrone + TX, 6-Ethyl-5,7-dioxo-pyrrole[4,5][1,4]dithiino[1,2-c]isothiazole-3-carbonitrile + TX, 2-(Difluoromethy) (R)-3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide + TX, 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine + TX, 4-(2-bromo -4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine + TX, fluindapyr + TX, koumethoxystrobin (jiaxiangjunzhi) + TX, lvbenmixianan + TX, diclobenziazox + TX, mandestrobin + TX, 3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1-yl)quinolone + TX, 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phenyl]propionate + TX, lopan-2-ol + TX, oxathiapiproline + TX, tert-butyl N-[6-[[[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate + TX, pyraziflumide + TX, impirflusam + TX, trolprocarb + TX, mefentrifluconazole + TX, ipfentrifluconazole + TX, 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide + TX, N'-(2,5-Dimethyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine + TX, N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidine + TX, [2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]thiazol-4-yl]-4,5-dihydroisoxazol-5-yl]-3-chloro- phenyl]methanesulfonate + TX, but-3-ynyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate + TX, methyl N-[[5-[4-(2,4-dimethylphenyl)triazol-2-yl]-2-methyl-phenyl]methyl]carbamate + TX, 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine + TX, pyridazine Dacromethyl + TX, 3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide + TX, 1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one + TX, 1-methyl-4-[3-methyl-2-[[2-methyl-4-(3,4,5-trimethylpyrazol-1-yl)phenoxy]methyl]phenyl]tetrazole Trazol-5-one + TX, aminopyrifen + TX, amethoctrazine + TX, amisulbrom + TX, penflufen + TX, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide + TX, florylpicoxamide + TX, fenpicoxamide + TX, tebufloquine + TX, ipflufenoquine + TX, quinofumelin + TX, isofetamide + TX, N-[2-[2,4-Dichloro-phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide + TX, N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide + TX, Benzothiostrobin + TX, Fenamacryl + TX, 5-Amino-1,3,4-thiadiazole-2-thiol zinc salt (2:1) + TX, Fluopyram + TX, Flutianil + TX, Fluopimomide +TX, pyrapropion +TX, picarbutrazox +TX, 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide +TX, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide +TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridine diethyl]oxy]benzonitrile + TX, methyltetraprole + TX, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide + TX, α-(1,1-dimethylethyl)-α-[4'-(trifluoromethoxy)[1,1'-biphenylphenyl]-4-yl]-5-pyrimidinemethanol + TX, fluoxapiproline + TX, enoxastrobin + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-di Fluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-sulfanyl-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-Triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX, Trinexapac + TX, Koumoxystrobin + TX, Zhongshengmycin + TX, Thiodiazole copper + TX, Zinc thiazole + TX, Amectotractin + TX, Iprodione + TX, N-Octyl-N'-[2-(octylamino)ethyl]ethane-1,2-diamine + TX; N'-[5-bromo-2-methyl-6-[(1S) -1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX , N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidine + TX (these compounds can be prepared according to the method described in WO 2015 / 155075); N'-[5-bromo- 2-Methyl-6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX (this compound can be prepared from the method described in IPCOM000249876D); N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenyl-ethyl)phenyl]-N-methyl-formamidine + TX, N'-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-methoxy-2-methyl-phenyl]-N-isopropyl-N-methyl-formamidine + TX (these compounds can be prepared according to the method described in WO 2018 / 228896); N-ethyl-N'-[5-methoxy-2-methyl-4-[2-trifluoromethyl)oxetan-2-yl]phenyl]-N-methyl-formamidine + TX, N-ethyl-N'-[5-methoxy-2-methyl-4-[2-trifluoromethyl]oxetan-2-yl]phenyl]-N-methyl-formamidine + TX )tetrahydrofuran-2-yl]phenyl]-N-methyl-formamidine + TX (these compounds can be prepared according to the method described in WO 2019 / 110427); N-[(1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide + TX N-[(1S)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline 8-Fluoro-N-[(1R)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide + TX, 8-Fluoro-N-[(1S)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide + TX, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide + TX, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide + TX, N-((1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide + TX, N-((1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide + TX (these compounds can be prepared according to the method described in WO 2017 / 153380); 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline + TX, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,6-trifluoro-3,3-dimethyl-isoquinoline + TX, 4,4-difluoro-3,3-dimethyl-1-(6-methylpyrazolo[1,5-a]pyridin-3 -yl)isoquinoline + TX, 4,4-difluoro-3,3-dimethyl-1-(7-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline + TX, 1-(6-chloro-7-methyl-pyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline + TX (these compounds were prepared according to the method described in WO 2017 / 025510). 1-(4,5-dimethylbenzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline + TX, 1-(4,5-dimethylbenzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline + TX, 6-chloro-4,4-difluoro-3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline + TX, 4,4-difluoro-1-(5-fluoro-4-methyl-benzimidazol-1-yl)-3,3-dimethyl-isoquinoline + TX, 3-(4,4-difluoro-3,3-dimethyl-1-isoquinolyl)-7,8-dihydro-6H-cyclopenta[e]benzimidazole + TX (these compounds can be prepared according to the method described in WO 2016 / 156085);N-Methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide + TX, N,2-Dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide + TX, N-Ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide + TX 1-Methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea + TX, 1,3-Dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea + TX, 3-Ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea + TX N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea + TX, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide + TX, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one + TX, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2 ,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one + TX, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylate + TX, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-1,2,4-triazol-3-amine + TX. The compounds of this paragraph can be prepared from the methods described in WO 2017 / 055473, WO 2017 / 055469, WO 2017 / 093348 and WO 2017 / 118689;2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol + TX (this compound can be prepared from the method described in WO 2017 / 029179); 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol + TX (this compound can be prepared from the method described in WO 2017 / 029179); 3 -[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile + TX (this compound can be prepared from the method described in WO 2016 / 156290); 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]imidazole-4-carbonitrile + TX (this compound can be prepared from the method described in WO 2016 / 156290); (4-phenoxyphen N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbazolyl)methyl 2-amino-6-methyl-pyridine-3-carboxylate + TX (this compound can be prepared from the method described in WO 2014 / 006945); 2,6-dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetrone + TX (this compound can be prepared from the method described in WO 2011 / 138281); N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbazolyl)methyl 2-amino-6-methyl-pyridine-3-carboxylate + TX (this compound can be prepared from the method described in WO 2014 / 006945); rubothioamide + TX; N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX; (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide + TX (this compound can be prepared from the method described in WO 2018 / 153707); N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine + TX;N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine + TX (this compound can be prepared from the method described in WO 2016 / 202742); 2-(difluoromethyl)-N-[(3S)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide + TX (this compound can be prepared from the method described in WO 2014 / 095675); (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazine (3-methylisoxazol-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methasone + TX, (3-methylisoxazol-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methasone + TX (these compounds can be prepared from the methods described in WO 2017 / 220485); 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide + TX (this compound can be prepared from the methods described in WO 2018 / 065414); ethyl 1- [[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate + TX (this compound can be prepared from the method described in WO 2018 / 158365); 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide + TX, N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX, N -[(Z)-Methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX, N-[N-Methoxy-C-methyl-carbonimidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + TX (these compounds can be prepared from the method described in WO 2018 / 202428), chlorinconazid + TX, seboctylamin + TX, chlorinconazin + TX, flumethylsulfolim + TX, fluoxythioconazole + TX;

[0130] The references in parentheses after the active ingredients, e.g. [3878-19-1], refer to the Chemical Abstracts Registry number. The above mentioned mixing partners are known. When the active ingredients are included in “The Pesticide Manual” [The Pesticide Manual-A World Compendium; Thirteenth Edition; Editor: CDS TomLin; The British Crop Protection Council], they are described therein under the entry number indicated in parentheses above for the particular compound, e.g. the compound “Abamectin” is described in entry number (1). When “[CCN]” is added above to a particular compound, the compound in question is included in the “Compendium of Pesticide Common Names”, which is accessible on the Internet [A. Wood; Compendium of Pesticide Common Names, Copyright c 1995-2004]. For example, the compound “acetoprole” is described under the Internet address http: / / www.alanwood.net / pesticides / acetoprole.html.

[0131] Most of the active ingredients mentioned above are referred to herein above as so-called "common names", with the relevant "ISO common name" or another "common name" being used in individual cases. If the designation is not a "common name", the nature of the designation used instead is given in parentheses for the particular compound. In that case, the IUPAC name, IUPAC / Chemical Abstracts name, "chemical name", "conventional name", "compound name" or "development code" is used, or if none of those names is a "common name", an "alternative name" is used. "CAS Reg. No" means Chemical Abstracts Registry Number.

[0132] The active ingredient mixtures of compounds of formula (I) selected from one of the compounds shown in Tables A-1 to A-26 or B-1 to B-44 (below) or from the compounds listed in Tables T1 or T2 (below) are preferably in a mixing ratio of 100:1 to 1:6000, in particular 50:1 to 1:50, more in particular 20:1 to 1:20, even more in particular 10:1 to 1:10, very in particular 5:1 and 1:5, with ratios of 2:1 to 1:2 being particularly preferred, and ratios of 4:1 to 2:1 being likewise preferred, in particular 1:1, or 5:1, or 5:2, or 5:3, or 5:4, or 4: 1, or 4:2, or 4:3, or 3:1, or 3:2, or 2:1, or 1:5, or 2:5, or 3:5, or 4:5, or 1:4, or 2:4, or 3:4, or 1:3, or 2:3, or 1:2, or 1:600, or 1:300, or 1:150, or 1:35, or 2:35, or 4:35, or 1:75, or 2:75, or 4:75, or 1:6000, or 1:3000, or 1:1500, or 1:350, or 2:350, or 4:350, or 1:750, or 2:750, or 4:750. These mixing ratios are by weight.

[0133] The mixtures described above can be used in methods of controlling pests comprising applying a composition comprising the mixtures described above to the pest or its environment, with the exception of methods of treating the human or animal body by surgery or therapy and diagnostic methods performed on the human or animal body.

[0134] Mixtures comprising the compounds shown in Tables A-1 to A-26 or B-1 to B-44 (below), or the compounds listed in Tables T1 or T2 (below), and one or more active ingredients as described above, can be applied, for example, in a single "ready mix" form, in combination spray mixtures consisting of separate formulations of a single active ingredient, such as "tank mixes", and in combined use of a single active ingredient when applied sequentially, i.e., one after the other within a reasonably short period of time, such as a few hours or days. The order of application of the compounds shown in Tables A-1 to A-26 or B-1 to B-44 (below), or the compounds listed in Tables T1 or T2 (below) and the active ingredient(s) is not essential to the practice of the invention.

[0135] The compounds of the present invention may also be used in combination with anthelmintic drugs. Such anthelmintics include compounds selected from the macrocyclic lactone class of compounds such as ivermectin, avermectin, abamectin, emamectin, epirimectin, doramectin, selamectin, moxidectin, nemadectin and milbemycin derivatives, as described in EP 357460, EP 444964 and EP 594291. Additional anthelmintics include semi-synthetic and biosynthetic avermectin / milbemycin derivatives, such as those described in US Pat. No. 5,015,630, WO 9415944 and WO 9522552. Additional anthelmintics include benzimidazoles, such as albendazole, cambendazole, fenbendazole, flubendazole, mebendazole, oxyfendazole, oxybendazole, parbendazole and other members of this class. Additional anthelmintics include imidazothiazoles and tetrahydropyrimidines such as tetramisole, levamisole, pyrantel pamoate, oxantel, or morantel. Additional anthelmintics include fluoxides such as triclabendazole and clorsulon, and cestocides such as praziquantel and epsiprantel.

[0136] The compounds of the present invention may be used in combination with derivatives and analogues of the paraherquamide / marcfortine class of anthelmintics, as well as antiparasitic oxazolines such as those disclosed in U.S. Pat. No. 5,478,855, U.S. Pat. No. 4,639,771 and German Patent No. 19520936.

[0137] The compounds of the invention may be used in combination with derivatives and analogues of the general class of dioxomorpholine antiparasitic agents described in WO 96 / 15121, and also in combination with anthelmintic active cyclic depsipeptides such as those described in WO 96 / 11945, WO 93 / 19053, WO 93 / 25543, EP 0 626 375, EP 0 382 173, WO 94 / 19334, EP 0 382 173 and EP 0 503 538.

[0138] The compounds of the invention may be used in combination with other ectoparasiticides; for example, fipronil; pyrethroids; organophosphates; insect growth regulators such as lufenuron; ecdysone agonists such as tebufenozide; neonicotinoids such as imidacloprid.

[0139] The compounds of the present invention may be used in combination with terpene alkaloids, particularly those disclosed in WO 95 / 19363 or WO 04 / 72086.

[0140] Other examples of such biologically active compounds with which the compounds of the present invention may be used in combination include, but are not limited to, the following: Organophosphates: Acephate, Azamethiphos, Azinphos-ethyl, Azinphos-methyl, Bromophos, Bromophos-ethyl, Cadusafos, Chlorethoxyphos, Chlorpyrifos, Chlorfenvinphos, Chlormephos, Demeton, Demeton-S-methyl, Demeton-S-methylsulfone, Diarifos, Diazinon, Dichlorvos, Dicrotophos, Dimethoate, Disulfoton, Ethion, Ethoprophos, Etrimphos, Fanfur, Fenamiphos, Fenitrothion, Fensulfothion, Fenthion, Flupyrazophos, Fonophos, Formothion, Fosthiazate, Heptenophos, Isazophos, Isothioate, Isoxathioate , malathion, methacrifos, methamidophos, methidathion, methyl-parathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, paraoxon, parathion, parathion-methyl, phenthoate, phosalone, phospholane, phosphocarb, phosmet, phosphamidon, phorate, phoxim, pirimiphos, pirimiphos-methyl, profenofos, propafos, proethamphos, prothiofos, pyraclofos, pyridapenthione, quinalphos, sulprofos, temephos, terbufos, tebupirimphos, tetrachlorvinphos, thimeton, triazophos, trichlorfon, vamidothion.

[0141] Carbamates: alanycarb, aldicarb, 2-sec-butylphenyl methylcarbamate, benfuracarb, carbaryl, carbofuran, carbosulfan, cloethocarb, ethiofencarb, fenoxycarb, fenthiocarb, furathiocarb, HCN-801, isoprocarb, indoxacarb, methiocarb, methomyl, 5-methyl-m-cumenylbutyryl (methyl)carbamate, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, UC-51717.

[0142] Pyrethroids: acrinathin, allethrin, alphamethrin, 5-benzyl-3-furylmethyl (E)-(1R)-cis-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate, bifenthrin, beta-cyfluthrin, cyfluthrin, alpha-cypermethrin, beta-cypermethrin, bioallethrin, bioallethrin ((S)-cyclopentyl isomer), bioresmethrin, bifenthrin, NCI-85193, cycloprothrin, cyhalothrin , cycythrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenfluthrin, fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (D isomer), imiprothrin, cyhalothrin, λ-cyhalothrin, permethrin, fenothrin, prallethrin, pyrethrins (natural products), resmethrin, tetramethrin, transfluthrin, θ-cypermethrin, silafluofen, t-fluvalinate, tefluthrin, tralomethrin, ζ-cypermethrin.

[0143] Arthropod growth regulators: a) Chitin synthesis inhibitors: Benzoyl ureas: Chlorfluazuron, Diflubenzuron, Fluazuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Teflubenzuron, Triflumuron, Buprofezin, Diofenolan, Hexythiazox, Etoxazole, Chlorfentadine; b) Ecdysone antagonists: Halofenozide, Methoxyfenozide, Tebufenozide; c) Juvenoids: Pyriproxyfen, Methoprene (including S-methoprene), Fenoxycarb; d) Lipid biosynthesis inhibitors: Spirodiclofen.

[0144] Other antiparasitic drugs: Acequinocyl, Amitraz, AKD-1022, ANS-118, Azadirachtin, Bacillus thuringiensis thuringiensis), bensultap, bifenazate, binapacryl, bromopropylate, BTG-504, BTG-505, campechlor, cartap, chlorobenzilate, chlordimeform, chlorfenapyr, chromafenozide, clothianidine, cyromazine, diacloride, diafenthiuron, DBI-3204, dinactin, dihydroxymethyldihydroxypyrrolidine, dinobuton, dinocap, endosulfan, ethiprole, etofenprox, fenazaquin, flumite, MTI-800, fenpyroximate, fluacrypyrim, flubenzimine, flubrocythrinate, fluphenzin, flufenprox, fluproxifen, halofenprox ofenprox), hydramethylnon, IKI-220, Kanemite, NC-196, Nimgard, Nidinolterfuran, Nitenpyram, SD-35651, WL-108477, pyridalyl, propargite, protrifenbut, pymethrozine, pyridaben, pyrimidifen, NC-1111, R-195, RH-0345, RH-2485, RYI-210, S-1283, S-1833, SI-8601, silafluofen, cyromazine, spinosad, tebufenpyrad, tetradifon, tetranactin, thiacloprid, thiocyclam, thiamethoxam, tolfenpyrad, triazamate, triethoxyspinosin, trinactin, belbutin, bertarek, YI-5301.

[0145] Biological agents: Bacillus thuringiensis ssp aizawai, kurstaki, Bacillus thuringiensis delta endotoxin, baculovirus, entomopathogenic bacteria, viruses and fungi.

[0146] Fungicides: Chlortetracycline, oxytetracycline, streptomycin.

[0147] Other biological agents: Enrofloxacin, Febantel, Penethamate, Moroxicam, Cephalexin, Kanamycin, Pimobendan, Clenbuterol, Omeprazole, Tiamulin, Benazepril, Pyriprole, Cefquinome, Florfenicol, Buserelin, Cefovecin, Tulathromycin, Ceftiowol, Carprofen, Metaflumizone, Praziquarantel, Triclabendazole.

[0148] The compositions according to the invention may also comprise further solid or liquid auxiliaries, such as stabilizers, e.g. unepoxidized or epoxidized vegetable oils (e.g. epoxidized coconut oil, rapeseed oil or soybean oil), antifoaming agents, e.g. silicone oils, preservatives, viscosity regulators, binders and / or adhesives, fertilizers or other active ingredients to achieve a particular effect, e.g. fungicides, bactericides / fungicides, nematicides, plant activators, molluscicides or herbicides.

[0149] The compositions according to the invention are prepared in a manner known per se in the absence of auxiliaries, for example by pulverizing, screening and / or compressing the solid active ingredient, and in the presence of at least one auxiliary, for example by intimately mixing and / or pulverizing the active ingredient with one or more auxiliary agents. These preparation processes of the compositions and the use of compound (I) for preparing these compositions are also the subject of the present invention.

[0150] Another aspect of the present invention relates to the use of a compound of formula (I) or a preferred individual compound as defined herein, a composition comprising at least one compound of formula (I) or at least one preferred individual compound as defined above, or a fungicidal or insecticidal mixture comprising at least one compound of formula (I) or at least one preferred individual compound as defined above, in admixture with other fungicides or insecticides as defined above, for controlling or preventing infestation on plants, e.g. useful plants, such as crop plants, their propagation material, e.g. seeds, harvested crops, e.g. harvested food crops, or non-living material by phytopathogenic microorganisms, e.g. insects or preferably fungal organisms.

[0151] A further aspect of the invention relates to a method for controlling or preventing infestation on plants, e.g. useful plants, such as crop plants, their propagation material, e.g. seeds, harvested crops, e.g. harvested food crops, or non-living material by insects or spoilage microorganisms or organisms that are phytopathogenic or potentially harmful to humans, especially fungal organisms, which method comprises the step of applying a compound of formula (I) or a preferred individual compound as defined above as an active ingredient to the plant, to a part of the plant or its habitat, to its propagation material, or to any part of the non-living material.

[0152] By control or prevention is meant reducing infestation by plant pathogenic or spoilage microorganisms or organisms that are potentially harmful to humans, particularly fungal organisms, to a level that demonstrates improvement.

[0153] A preferred method for controlling or preventing infestation of crop plants by phytopathogenic microorganisms, especially fungal organisms, or insects, which involves the application of a compound of formula (I) or an agrochemical composition containing at least one of said compounds, is foliar treatment. The frequency and amount of application will depend on the risk of infestation by the corresponding pathogen or insect. However, the compound of formula (I) can also be introduced into the plant by the roots via the soil (systemic action) by irrigating the plant habitat with a liquid formulation or by applying the compound to the soil in solid form, for example in granular form (soil application). In the case of rice crops, such granules can be applied to flooded rice fields. The compound of formula (I) can also be applied to seeds (coating) by impregnating the seeds or tubers with a liquid formulation of the fungicide or by coating them with a solid formulation.

[0154] Formulations, e.g. compositions containing a compound of formula (I) and, if desired, a solid or liquid auxiliary or monomer that encapsulates the compound of formula (I), may be prepared in a known manner, typically by homogeneously mixing and / or grinding the compounds together with extenders, e.g. solvents, solid carriers and, optionally, surface-active compounds (surfactants).

[0155] Advantageous application rates are usually from 5 g to 2 kg of active ingredient (ai) per hectare (ha), preferably from 10 g to 1 kg ai / ha, most preferably from 20 g to 600 g ai / ha.When used as a seed drench, a convenient dosage is from 10 mg to 1 g of active substance per kg of seeds.

[0156] When the combinations of the invention are used for seed treatment, an amount of 0.001 to 50 g of a compound of formula (I) per kg of seed, preferably 0.01 to 10 g per kg of seed, will generally be sufficient.

[0157] Preferably, the compositions comprising the compounds of formula (I) according to the present invention are applied prophylactically, meaning before the onset of a disease, or therapeutically, meaning after the onset of a disease.

[0158] The compositions of the present invention may be in any conventional form, such as, for example, two-part systems, dry seed treatment powders (DS), seed treatment emulsions (ES), seed treatment flowable concentrates (FS), seed treatment solutions (LS), seed treatment water dispersible powders (WS), seed treatment capsule suspensions (CF), seed treatment gels (GF), emulsion concentrates (EC), suspension concentrates (SC), suspoemulsions (SE), capsule suspensions (CS), water dispersible granules (WG), emulsifiable granules (WG), sorbent granules (RM ... The present invention may be employed in the form of an emulsion, such as an EG, an emulsion, a water-in-oil (EO), an emulsion, an oil-in-water (EW), a microemulsion (ME), an oil dispersion (OD), an oil-miscible fluid (OF), an oil-miscible liquid (OL), a soluble concentrate (SL), a very low volume suspension (SU), a very low volume liquid (UL), a technical concentrate (TK), a dispersible concentrate (DC), a wettable powder (WP), or any technically desirable formulation in combination with an agriculturally acceptable adjuvant.

[0159] Such compositions can be produced in a conventional manner, for example by mixing the active ingredient with suitable inert compounding agents (diluents, solvents, fillers, and optionally other compounding agents such as surfactants, biocides, antifreeze agents, spreading agents, thickeners, and compounds providing adjuvant activity effects). Conventional slow-release formulations can also be employed when long-lasting efficacy is intended. In particular, formulations applied in spray form, such as water-dispersible concentrates (e.g., EC, SC, DC, OD, SE, EW, EO, etc.), wettable powders, and granules, may contain surfactants such as wetting and dispersing agents and other compounds providing adjuvant effects, such as, for example, condensates of formaldehyde with naphthalene sulfonates, alkylaryl sulfonates, lignin sulfonates, fatty alkyl sulfates, and ethoxylated alkylphenols and ethoxylated fatty alcohols.

[0160] The seed dressing formulation is applied to the seed in a manner known per se, utilizing the combination and diluent of the present invention in a suitable seed dressing formulation form, such as an aqueous suspension or a dry powder form with good adhesion to the seed. Such seed dressing formulations are known in the art. The seed dressing formulation may contain a single active ingredient or a combination of active ingredients in encapsulated form, for example as a slow release capsule or microcapsule.

[0161] Usually, the formulations contain 0.01-90% by weight of active agent, 0-20% of agriculturally acceptable surfactants, and 10-99.99% of solid or liquid inert compounding agents and adjuvants, the active agent being at least a compound of formula (I), optionally together with other active agents, in particular fungicides or preservatives. Concentrated forms of the composition generally contain about 2-80%, preferably about 5-70% by weight of active agent. Application forms of the formulations may contain, for example, 0.01-20% by weight, preferably 0.01-5% by weight of active agent. Commercial products will preferably be formulated as concentrates, but end users will usually utilize diluted formulations.

[0162] Although it is preferred to formulate commercial products as concentrates, end users will typically dilute the formulations when used.

[0163] The compounds listed in the following Tables A-1 to A-26 and B-1 to B-44 can be prepared according to the above-mentioned methods. The following examples are intended to illustrate the present invention and to show preferred compounds of formula (I).

[0164] Table A: This table shows compounds of formula (Ia) according to the invention: [ka] (Wherein, G(-N(H)-, R 2 , R 3 and R 4 (including) is expressed by the following formula [ka] wherein the G substituents are as defined below. The document discloses definitions of 59 substituents of the compound (G).

[0165] [Table 1-1] [Table 1-2] [Table 1-3]

[0166] Thus, the following compounds are specifically depicted in Tables A-1 through A-26 with the substituents of formula (Ia) below.

[0167] Table A-1: ​​This table shows that A is A-1 and R is 1 is phenyl, and R 5 is hydrogen and R 6 is methyl and the G substituents are as defined in Table A above. For example, compound A-1.20 has the following structure: [ka] Compound A-1.20

[0168] Table A-2: This table shows that A is A-1 and R is 1 is 6-chloropyridin-3-yl, R 5 is hydrogen and R 6 is methyl and the G substituents are as defined in Table A above.

[0169] Table A-3: This table shows that A is A-1 and R is 1 is 3-trifluoromethylphenyl, R 5is hydrogen and R 6 is methyl and the G substituents are as defined in Table A above.

[0170] Table A-4: This table shows that A is A-1 and R is 1 is 3-methoxyphenyl, and R 5 is hydrogen and R 6 is methyl and the G substituents are as defined in Table A above.

[0171] Table A-5: This table shows that A is A-1 and R is 1 is 3-cyclopropylphenyl, R 5 is hydrogen and R 6 is methyl and the G substituents are as defined in Table A above.

[0172] Table A-6: This table shows that A is A-2 and R is 1 is phenyl, and R 7 is hydrogen and R 8 is chloro and the G substituent is as defined in Table A above.

[0173] Table A-7: This table shows that A is A-2 and R is 1 is 6-chloropyridin-3-yl, R 7 is hydrogen and R 8 is chloro and the G substituent is as defined in Table A above.

[0174] Table A-8: This table shows that A is A-2 and R is 1 is 3-trifluoromethylphenyl, R 7 is hydrogen and R 8is chloro and the G substituent is as defined in Table A above.

[0175] Table A-9: This table shows that A is A-2 and R is 1 is 3-methoxyphenyl, and R 7 is hydrogen and R 8 is chloro and the G substituent is as defined in Table A above.

[0176] Table A-10: This table shows that A is A-2 and R is 1 is 3-cyclopropylphenyl, R 7 is hydrogen and R 8 is chloro and the G substituent is as defined in Table A above.

[0177] Table A-11: This table shows that A is A-2 and R is 1 is phenyl, and R 7 is hydrogen and R 8 is methyl and the G substituents are as defined in Table A above.

[0178] Table A-12: This table shows that A is A-2 and R is 1 is 6-chloropyridin-3-yl, R 7 is hydrogen and R 8 is methyl and the G substituents are as defined in Table A above.

[0179] Table A-13: This table shows that A is A-2 and R is 1 is 3-trifluoromethylphenyl, R 7 is hydrogen and R 8is methyl and the G substituents are as defined in Table A above.

[0180] Table A-14: This table shows that A is A-2 and R is 1 is 3-methoxyphenyl, and R 7 is hydrogen and R 8 is methyl and the G substituents are as defined in Table A above.

[0181] Table A-15: This table shows that A is A-2 and R is 1 is 3-cyclopropylphenyl, R 7 is hydrogen and R 8 is methyl and the G substituents are as defined in Table A above.

[0182] Table A-16: This table shows that A is A-2 and R is 1 is 3-cyclopropylphenyl, R 7 is hydrogen and R 8 is hydrogen and the G substituents are as defined in Table A above.

[0183] Table A-17: This table shows that A is A-2 and R is 1 is 3-cyclopropylphenyl, R 7 is hydrogen and R 8 is methoxy and the G substituent is as defined in Table A above.

[0184] Table A-18: This table shows that A is A-2 and R is 1 is 3-cyclopropyl-2-fluorophenyl, R 7 is hydrogen and R 8is methoxy and the G substituent is as defined in Table A above.

[0185] Table A-19: This table shows that A is A-2 and R is 1 is 3-cyclopropylphenyl, R 7 is hydrogen and R 8 is isopropyl and the G substituents are as defined in Table A above.

[0186] Table A-20: This table shows that A is A-2 and R is 1 is 3-chlorophenyl, and R 7 is ethyl, and R 8 is isopropyl and the G substituents are as defined in Table A above.

[0187] Table A-21: This table shows that A is A-2 and R is 1 is 3-cyclopropylphenyl, R 7 is hydrogen and R 8 is ethyl and the G substituents are as defined in Table A above.

[0188] Table A-22: This table shows that A is A-2 and R is 1 is 3-cyclopropylphenyl, R 7 is hydrogen and R 8 is isopropoxy and the G substituents are as defined in Table A above.

[0189] Table A-23: This table shows that A is A-2 and R is 1 is 3-cyclopropylphenyl, R 7 is hydrogen and R 8is 2-methylallyloxy and the G substituent is as defined in Table A above.

[0190] Table A-24: This table shows that A is A-2 and R is 1 is 3-cyclopropylphenyl, R 7 is hydrogen and R 8 is isopropenyl and the G substituents are as defined in Table A above.

[0191] Table A-25: This table shows that A is A-2 and R is 1 is 3-cyclopropylphenyl, R 7 is hydrogen and R 8 is cyclopropyl and the G substituent is as defined in Table A above.

[0192] Table A-26: This table shows that A is A-2 and R is 1 is 3-cyclopropylphenyl, R 7 is hydrogen and R 8 is 2-cyclopropylethynyl and the G substituent is as defined in Table A above.

[0193] Table B: This table shows compounds of formula (Ia) according to the present invention: [ka] (Wherein, G(-N(H)-, R 2 , R 3 and R 4 (including [ka] (In the formula, R 1 The substituents are as defined below. is) Definitions of 58 substituents for the compound (R 1 ) has been disclosed.

[0194] [Table 2]

[0195] Thus, the following compounds are specifically depicted in Tables B-1 to B-44 with the substituents of formula (Ia) below.

[0196] Table B-1: This table shows that A is A-1 and R 5 is hydrogen and R 6 is methyl, G is [2-(6-chloro-3-pyridyl)ethyl]amino, and R 1 There are provided 58 compounds B-1.01 and B-1.58 of formula (Ia) in which the substituents are as defined in Table B above.

[0197] Table B-2: This table shows that A is A-1 and R 5 is hydrogen and R 6 is methyl, G is [2-(2,4-dimethylphenyl)ethyl]amino, and R 1 There are provided 58 compounds B-2.01 and B-2.58 of formula (Ia) in which the substituents are as defined in Table B above.

[0198] Table B-3: This table shows that A is A-1 and R 5 is hydrogen and R 6 is methyl, G is [2-(2,4-dimethylphenyl)-2-fluoro-ethyl]amino, and R 1 There are provided 58 compounds B-3.01 and B-3.58 of formula (Ia) in which the substituents are as defined in Table B above.

[0199] Table B-4: This table shows that A is A-1 and R 5 is hydrogen and R 6 is methyl, G is [(2S)-2-(2,4-dimethylphenyl)-2-fluoro-ethyl]amino, and R 1There are provided 58 compounds B-4.01 and A-4.58 of formula (Ia) in which the substituents are as defined in Table B above.

[0200] Table B-5: This table shows that A is A-1 and R 5 is hydrogen and R 6 is methyl, G is [(2S)-2-(2,4-dimethylphenyl)-2-fluoro-ethyl]amino, and R 1 There are provided 58 compounds B-5.01 and A-5.58 of formula (Ia) in which the substituents are as defined in Table B above.

[0201] Table B-6: This table shows that A is A-1 and R 5 is hydrogen and R 6 is methyl, G is [2-(2,4-dichlorophenyl)ethyl]amino, and R 1 There are provided 58 compounds B-6.01 and B-6.58 of formula (Ia) in which the substituents are as defined in Table B above.

[0202] Table B-7: This table shows that A is A-1 and R 5 is hydrogen and R 6 is methyl, G is [2-(2,4-dichlorophenyl)-2-fluoro-ethyl]amino, and R 1 There are provided 58 compounds B-7.01 and B-7.58 of formula (Ia) in which the substituents are as defined in Table B above.

[0203] Table B-8: This table shows that A is A-1 and R 5 is hydrogen and R 6 is methyl, G is [(2S)-2-(2,4-dichlorophenyl)-2-fluoro-ethyl]amino, and R 1 There are provided 58 compounds B-8.01 and B-8.58 of formula (Ia) in which the substituents are as defined in Table B above.

[0204] Table B-9: This table shows that A is A-1 and R 5 is hydrogen and R 6is methyl, G is [(2R)-2-(2,4-dichlorophenyl)-2-fluoro-ethyl]amino, and R 1 There are provided 58 compounds B-9.01 and B-9.58 of formula (Ia) in which the substituents are as defined in Table B above.

[0205] Table B-10: This table shows that A is A-2 and R 7 is hydrogen and R 8 is chloro, G is [2-(6-chloro-3-pyridyl)ethyl]amino, and R 1 Provided are 58 compounds B-10.01 and B-10.57 of formula (Ia) in which the substituents are as defined in Table B above. For example, compound B-10.9 has the following structure: [ka] Compound B-10.9

[0206] Table B-11: This table shows that A is A-2 and R 7 is hydrogen and R 8 is chloro, G is [2-(2,4-dimethylphenyl)ethyl]amino, and R 1 Provided are 58 compounds B-11.01 and B-11.58 of formula (Ia), in which the substituents are as defined in Table B above.

[0207] Table B-12: This table shows that A is A-2 and R 7 is hydrogen and R 8 is chloro, G is [2-(2,4-dimethylphenyl)-2-fluoro-ethyl]amino, and R 1 There are provided 58 compounds B-12.01 and B-12.58 of formula (Ia) in which the substituents are as defined in Table B above.

[0208] Table B-13: This table shows that A is A-2 and R 7 is hydrogen and R 8 is chloro, G is [(2S)-2-(2,4-dimethylphenyl)-2-fluoro-ethyl]amino, and R1 There are provided 58 compounds B-13.01 and A-13.58 of formula (Ia) in which the substituents are as defined in Table B above.

[0209] Table B-14: This table shows that A is A-2 and R 7 is hydrogen and R 8 is chloro, G is [(2R)-2-(2,4-dimethylphenyl)-2-fluoro-ethyl]amino, and R 1 There are provided 58 compounds B-14.01 and A-14.58 of formula (Ia) in which the substituents are as defined in Table B above.

[0210] Table B-15: This table shows that A is A-2 and R 7 is hydrogen and R 8 is chloro, G is [2-(2,4-dichlorophenyl)ethyl]amino, and R 1 Provided are 58 compounds B-15.01 and B-15.58 of formula (Ia), wherein the substituents are as defined in Table B above.

[0211] Table B-16: This table shows that A is A-2 and R 7 is hydrogen and R 8 is chloro, G is [2-(2,4-dichlorophenyl)-2-fluoro-ethyl]amino, and R 1 Provided are 57 compounds B-16.01 and B-16.58 of formula (Ia), in which the substituents are as defined in Table B above.

[0212] Table B-17: This table shows that A is A-2 and R 7 is hydrogen and R 8 is chloro, G is [(2S)-2-(2,4-dichlorophenyl)-2-fluoro-ethyl]amino, and R 1 Provided are 58 compounds B-17.01 and B-17.58 of formula (Ia), wherein the substituents are as defined in Table B above.

[0213] Table B-18: This table shows that A is A-2 and R 7 is hydrogen and R 8is chloro, G is [(2R)-2-(2,4-dichlorophenyl)-2-fluoro-ethyl]amino, and R 1 There are provided 58 compounds B-18.01 and B-18.58 of formula (Ia) in which the substituents are as defined in Table B above.

[0214] Table B-19: This table shows that A is A-2 and R 7 is hydrogen and R 8 is methyl, G is [2-(6-chloro-3-pyridyl)ethyl]amino, and R 1 Provided are 58 compounds B-19.01 and B-19.58 of formula (Ia), wherein the substituents are as defined in Table B above.

[0215] Table B-20: This table shows that A is A-2 and R is 7 is hydrogen and R 8 is methyl, G is [2-(2,4-dimethylphenyl)ethyl]amino, and R 1 There are provided 58 compounds B-20.01 and B-20.58 of formula (Ia) in which the substituents are as defined in Table B above.

[0216] Table B-21: This table shows that A is A-2 and R 7 is hydrogen and R 8 is methyl, G is [2-(2,4-dimethylphenyl)-2-fluoro-ethyl]amino, and R 1 There are provided 58 compounds B-21.01 and B-21.58 of formula (Ia) in which the substituents are as defined in Table B above.

[0217] Table B-22: This table shows that A is A-2 and R is 7 is hydrogen and R 8 is methyl, G is [(2S)-2-(2,4-dimethylphenyl)-2-fluoro-ethyl]amino, and R 1 There are provided 58 compounds B-22.01 and A-22.58 of formula (Ia) in which the substituents are as defined in Table B above.

[0218] Table B-23: This table shows that A is A-2 and R 7 is hydrogen and R 8 is methyl, G is [(2R)-2-(2,4-dimethylphenyl)-2-fluoro-ethyl]amino, and R 1 There are provided 58 compounds B-23.01 and B-23.58 of formula (Ia), wherein the substituents are as defined in Table B above.

[0219] Table B-24: This table shows that A is A-2 and R is 7 is hydrogen and R 8 is methyl, G is [2-(2,4-dichlorophenyl)ethyl]amino, and R 1 There are provided 58 compounds B-24.01 and B-24.58 of formula (Ia) in which the substituents are as defined in Table B above.

[0220] Table B-25: This table shows that A is A-2 and R is 7 is hydrogen and R 8 is methyl, G is [2-(2,4-dichlorophenyl)-2-fluoro-ethyl]amino, and R 1 There are provided 58 compounds B-25.01 and B-25.58 of formula (Ia), wherein the substituents are as defined in Table B above.

[0221] Table B-26: This table shows that A is A-2 and R 7 is hydrogen and R 8 is methyl, G is [(2S)-2-(2,4-dichlorophenyl)-2-fluoro-ethyl]amino, and R 1 There are provided 58 compounds B-26.01 and B-26.58 of formula (Ia), wherein the substituents are as defined in Table B above.

[0222] Table B-27: This table shows that A is A-2 and R 7 is hydrogen and R 8 is methyl, G is [(2R)-2-(2,4-dichlorophenyl)-2-fluoro-ethyl]amino, and R 1There are provided 58 compounds B-27.01 and B-27.58 of formula (Ia) in which the substituents are as defined in Table B above.

[0223] Table B-28: This table shows that A is A-2 and R 7 is hydrogen and R 8 is hydrogen, G is [2-(2,4-dichlorophenyl)-2-fluoro-ethyl]amino, and R 1 There are provided 58 compounds B-28.01 and B-28.58 of formula (Ia) in which the substituents are as defined in Table B above.

[0224] Table B-29: This table shows that A is A-2 and R 7 is hydrogen and R 8 is methoxy, G is [2-(2,4-dichlorophenyl)-2-fluoro-ethyl]amino, and R 1 There are provided 58 compounds B-29.01 and B-29.58 of formula (Ia), wherein the substituents are as defined in Table B above.

[0225] Table B-30: This table shows that A is A-2 and R is 7 is hydrogen and R 8 is methoxy, G is [2-(2,4-dichlorophenyl)ethyl]amino, and R 1 There are provided 58 compounds B-30.01 and B-30.58 of formula (Ia) in which the substituents are as defined in Table B above.

[0226] Table B-31: This table shows that A is A-2 and R 7 is hydrogen and R 8 is hydrogen, G is [2-(2,4-dichlorophenyl)-2-fluoro-ethyl]amino, and R 1 There are provided 58 compounds B-31.01 and B-31.58 of formula (Ia) in which the substituents are as defined in Table B above.

[0227] Table B-32: This table shows that A is A-2 and R 7 is hydrogen and R 8is isopropyl, G is [(2S)-(2,4-dichlorophenyl)-2-fluoro-ethyl]amino, and R 1 There are provided 58 compounds B-32.01 and B-32.58 of formula (Ia) in which the substituents are as defined in Table B above.

[0228] Table B-33: This table shows that A is A-2 and R 7 is hydrogen and R 8 is isopropyl, G is [(2R)-(2,4-dichlorophenyl)-2-fluoro-ethyl]amino, R 1 There are provided 58 compounds B-33.01 and B-33.58 of formula (Ia), in which the substituents are as defined in Table B above.

[0229] Table B-34: This table shows that A is A-2 and R 7 is hydrogen and R 8 is isopropyl, G is [(2S)-(2,4-dimethylphenyl)-2-fluoro-ethyl]amino, and R 1 There are provided 58 compounds B-34.01 and B-34.58 of formula (Ia), wherein the substituents are as defined in Table B above.

[0230] Table B-35: This table shows that A is A-2 and R 7 is hydrogen and R 8 is isopropyl, G is [(2R)-(2,4-dimethylphenyl)-2-fluoro-ethyl]amino, R 1 There are provided 58 compounds B-35.01 and B-35.58 of formula (Ia), wherein the substituents are as defined in Table B above.

[0231] Table B-36: This table shows that A is A-2 and R 7 is hydrogen and R 8 is ethyl, G is [2-(2,4-dichlorophenyl)-2-fluoro-ethyl]amino, and R 1 There are provided 58 compounds B-36.01 and B-36.58 of formula (Ia), wherein the substituents are as defined in Table B above.

[0232] Table B-37: This table shows that A is A-2 and R 7 is hydrogen and R 8 is isopropoxy, G is [(2S)-(2,4-dichlorophenyl)-2-fluoro-ethyl]amino, and R 1 There are provided 58 compounds B-37.01 and B-37.58 of formula (Ia), wherein the substituents are as defined in Table B above.

[0233] Table B-38: This table shows that A is A-2 and R 7 is hydrogen and R 8 is isopropoxy, G is [(2R)-(2,4-dichlorophenyl)-2-fluoro-ethyl]amino, and R 1 There are provided 58 compounds B-38.01 and B-38.58 of formula (Ia) in which the substituents are as defined in Table B above.

[0234] Table B-39: This table shows that A is A-2 and R 7 is hydrogen and R 8 is isopropoxy, G is [(2S)-(2,4-dimethylphenyl)-2-fluoro-ethyl]amino, and R 1 There are provided 58 compounds B-39.01 and B-39.58 of formula (Ia), wherein the substituents are as defined in Table B above.

[0235] Table B-40: This table shows that A is A-2 and R is 7 is hydrogen and R 8 is isopropoxy, G is [(2R)-(2,4-dimethylphenyl)-2-fluoro-ethyl]amino, and R 1 There are provided 58 compounds B-40.01 and B-40.58 of formula (Ia) in which the substituents are as defined in Table B above.

[0236] Table B-41: This table shows that A is A-2 and R 7 is hydrogen and R 8is 2-methylallyloxy, G is [2-(2,4-dichlorophenyl)-2-fluoro-ethyl]amino, and R 1 There are provided 58 compounds B-41.01 and B-41.58 of formula (Ia) in which the substituents are as defined in Table B above.

[0237] Table B-42: This table shows that A is A-2 and R 7 is hydrogen and R 8 is isopropenyl, G is [2-(2,4-dichlorophenyl)-2-fluoro-ethyl]amino, and R 1 There are provided 58 compounds B-42.01 and B-42.58 of formula (Ia) in which the substituents are as defined in Table B above.

[0238] Table B-43: This table shows that A is A-2 and R 7 is hydrogen and R 8 is cyclopropyl, G is [2-(2,4-dichlorophenyl)-2-fluoro-ethyl]amino, and R 1 There are provided 58 compounds B-43.01 and B-43.58 of formula (Ia), in which the substituents are as defined in Table B above.

[0239] Table B-44: This table shows that A is A-2 and R 7 is hydrogen and R 8 is 2-cyclopropylethynyl, G is [2-(2,4-dichlorophenyl)-2-fluoro-ethyl]amino, and R 1 There are provided 58 compounds B-44.01 and B-44.58 of formula (Ia), wherein the substituents are as defined in Table B above. EXAMPLES

[0240] The following examples illustrate the invention.

[0241] The compounds of the present invention can be distinguished from known compounds by their higher efficacy at low application rates, which can be verified by one skilled in the art using the experimental procedures outlined in the Examples and using lower application rates, such as 50 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1.5 ppm, 0.8 ppm, or 0.2 ppm, if necessary.

[0242] The compounds of formula (I) may have a number of benefits including, inter alia, advantageous levels of biological activity for the protection of plants against diseases caused by fungi, or superior properties for use as agrochemical active ingredients (e.g. high biological activity, advantageous spectrum of activity, enhanced safety profile (including improved crop tolerance), improved physicochemical properties, or increased biodegradability).

[0243] Throughout this specification, temperatures are given in degrees Celsius (° C.) and "mp." means melting point. LC / MS means liquid chromatography mass spectrometry, and a description of the apparatus and method A follows.

[0244] Method A: Spectra were recorded on a Waters mass spectrometer (SQD, SQDII single quadrupole mass spectrometer) equipped with an electrospray source (polarity: positive and negative ions), capillary: 3.00 kV, cone range: 30 V, extractor: 2.00 V, source temperature: 150 °C, desolvation temperature: 350 °C, cone gas flow: 50 l / h, desolvation gas flow: 650 L / h, mass range: 100-900 Da) and a Waters Acquity UPLC: binary pump, heated column compartment, diode array detector and ELSD detector. Column: Waters UPLC HSS T3, 1.8 μm, 30 × 2.1 mm; Temperature: 60 °C; DAD wavelength range (nm): 210 to 500; Solvent gradient: A = water + 5% MeOH + 0.05% HCOOH, B = acetonitrile + 0.05% HCOOH; Gradient: 10 to 100% B in 1.2 min; Flow rate (mL / min) 0.85

[0245] Method B: Spectra were recorded on a Waters mass spectrometer (SQD2 or QDA Single quadrupole mass spectrometer) equipped with an electrospray source (polarity: switched positive and negative), capillary: 0.8-3.00 kV, cone range: 25, source temperature: 120-150 °C, desolvation temperature: 500-600 °C, cone gas flow: 50 L / h, desolvation gas flow: 1000 L / h, mass range: 110-850 Da), and a Waters Acquity UPLC: quaternary solvent manager, heated column compartment, and diode array detector. Column: Acquity UPLC HSS T3 C18, 1.8 μm, 30x2.1 mm, Temperature: 40 °C, DAD wavelength range (nm): 200-400, Solvent gradient: A = water + 5% acetonitrile + 0.1% HCOOH, B = acetonitrile + 0.05% HCOOH: Gradient: 0 min 10% B; 0-0.2 min 10-50% B; 0.2-0.6 min 50-100% B; 0.6-1.3 min 100% B; 1.3-1.4 min 100-10% B; 1.4-1.6 min 10% B; Flow rate (mL / min) 0.6.

[0246] Method C: Spectra were recorded on a Waters mass spectrometer (SQD2 or QDA Single quadrupole mass spectrometer) equipped with an electrospray source (polarity: reversible positive / negative), capillary: 0.8-3.00 kV, cone range: 25, source temperature: 120-150 °C, desolvation temperature: 500-600 °C, cone gas flow: 50 L / h, desolvation gas flow: 1000 L / h, mass range: 110-850 Da) and a Waters Acquity UPLC: quaternary solvent manager, heated column compartment, diode array detector. Column: Acquity UPLC HSS T3 C18, 1.8 μm, 30x2.1 mm, Temperature: 40 °C, DAD wavelength range (nm): 200-400, Solvent gradient: A = water + 5% acetonitrile + 0.1% HCOOH, B = acetonitrile + 0.05% HCOOH: Gradient: 0 min 10% B; 0.0-0.5 min 10% B; 0.5-2 min 100% B; 2-3 min 100% B; 3-3.5 min 10% B; 3.5-4 min 10% B; Flow rate (mL / min) 0.6.

[0247] Method D: Spectra were recorded on a Waters mass spectrometer (SQD2 or QDA Single quadrupole mass spectrometer) equipped with an electrospray source (polarity: reversible positive / negative), capillary: 0.8-3.00 kV, cone range: 25, source temperature: 120-150 °C, desolvation temperature: 500-600 °C, cone gas flow: 50 L / h, desolvation gas flow: 1000 L / h, mass range: 110-850 Da) and a Waters Acquity UPLC: quaternary solvent manager, heated column compartment, diode array detector. Column: Waters UPLC HSS T3, 1.8 μm, 30 × 2.1 mm, Temperature: 40 °C, PDA wavelength range (nm): 200 to 400, Solvent gradient: A = water with 0.1% formic acid:acetonitrile: 95:5 v / v, B = acetonitrile with 0.05% formic acid, Gradient: 0 min-1.0 min, 10% B-90% A; 1.0 min-4.50 min 10%-100% B; 4.51 min-5.30 min, 100% B, 0% A; 5.31 min-5.50 min 100%-10% B; 5.51 min-6.00 min, 10% B, 90% A; Flow rate (ml / min) 0.6.

[0248] If desired, enantiomerically pure final compounds can be obtained from racemic material, if desired, via standard physical separation techniques such as reverse-phase chiral chromatography, or via stereoselective synthesis techniques, for example by using chiral starting materials.

[0249] If desired, enantiomerically pure final compounds can be obtained from racemic material, as appropriate, by standard physical separation techniques such as reverse-phase chiral chromatography, or by stereoselective synthesis techniques, for example by employing chiral starting materials.

[0250] Formulation examples

[0251] [Table 3]

[0252] The active ingredient is thoroughly mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill to obtain wettable powders which can be diluted with water to obtain a suspension of the desired concentration.

[0253] [Table 4]

[0254] The active ingredient is thoroughly mixed with the adjuvant and the mixture is thoroughly ground in a suitable mill to obtain a powder which can be used directly for seed treatment.

[0255] emulsifiable concentrate Active ingredient [compound of formula (I)] 10% Octylphenol polyethylene glycol ether 3% (4 to 5 moles of ethylene oxide) Calcium dodecylbenzenesulfonate 3% Castor oil polyglycol ether (ethylene oxide 35 moles) 4% Cyclohexanone 30% Xylene Mixture 50%

[0256] Emulsions of any required dilution which can be used for plant protection can be obtained from this concentrate by dilution with water.

[0257] [Table 5]

[0258] Ready-to-use dusts are obtained by mixing the active ingredient with the carrier and grinding the mixture in a suitable mill. Such powders can also be used in dry dressings for seeds.

[0259] Extrusion Granules Active ingredient [compound of formula (I)] 15% Sodium Lignosulfonate 2% Carboxymethylcellulose 1% Kaolin 82%

[0260] The active ingredient is mixed and ground with the adjuvants, the mixture is moistened with water, the mixture is extruded and then dried in a stream of air.

[0261] Coated Granules Active ingredient [compound of formula (I)] 8% Polyethylene glycol (molecular weight 200) 3% Kaolin 89%

[0262] The finely ground active ingredient is applied uniformly in a mixer to the kaolin moistened with polyethylene glycol, thus obtaining non-dusty coated granules.

[0263] Suspension concentrate Active ingredient [compound of formula (I)] 40% Propylene glycol 10% Nonylphenol polyethylene glycol ether (15 moles of ethylene oxide) 6% Sodium Lignosulfonate 10% Carboxymethylcellulose 1% Silicone oil (in the form of a 75% emulsion in water) 1% water 32%

[0264] The finely ground active ingredient is mixed homogeneously with the auxiliaries to obtain a suspension concentrate, which can be diluted with water to obtain any desired concentration, and can be used to treat and protect living plants and plant propagation material from microbial infestation by spraying, pouring or immersion.

[0265] Flowable concentrate for seed treatment Active ingredient [compound of formula (I)] 40% Propylene glycol 5% Copolymer butanol PO / EO 2% Tristyrene phenol with 10-20 moles EO 2% 1,2-Benzisothiazolin-3-one (in the form of a 20% aqueous solution) 0.5% Monoazo pigment calcium salt 5% Silicone oil (in the form of a 75% emulsion in water) 0.2% Water 45.3%

[0266] The finely ground active ingredient is mixed homogeneously with the auxiliaries to obtain a suspension concentrate, which can be diluted with water to obtain any desired concentration, and can be used to treat and protect living plants and plant propagation material from microbial infestation by spraying, pouring or immersion.

[0267] Slow-release capsule suspension 28 parts of the combined compounds of formula (I) are mixed with 2 parts of an aromatic solvent and 7 parts of a toluene diisocyanate / polymethylene-polyphenylisocyanate mixture (8:1). The mixture is emulsified in a mixture of 1.2 parts of polyvinyl alcohol, 0.05 parts of a defoamer, and 51.6 parts of water until the desired particle size is achieved. To the emulsion is added a mixture of 2.8 parts of 1,6-diaminohexane in 5.3 parts of water. The mixture is stirred until the polymerization reaction is complete.

[0268] The resulting capsule suspension is stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersant. The capsule suspension formulation contains 28% active ingredient. The medium capsule size is 8-15 microns.

[0269] The resulting formulation is applied to the seeds as an aqueous suspension in a device suitable for the purpose.

[0270] List of abbreviations: aq.=aqueous solution ℃ = degrees Celsius DCM = dichloromethane DMF = Dimethylformamide DMSO = dimethyl sulfoxide DMSO-d6 = deuterated dimethyl sulfoxide EtOAc = ethyl acetate equiv.=equivalent

[0271] HATU = N-[(dimethylamino)-1H-1,2,3-triazolo-[4,5-b]pyridin-1-ylmethylene]-N-methyl-methanaminium hexafluorophosphate N-oxide LCMS = Liquid Chromatography Mass Spectrometry (a description of the equipment and methods used for the LC / MS analysis is given above) M = molar concentration min=minutes mp = melting point N=normality T3P = 1-propanephosphonic anhydride ppm=parts per million RT=room temperature R t = retention time TLC = thin layer chromatography

[0272] Formulation examples The following examples further illustrate the invention without, however, limiting it. Those skilled in the art will readily recognize appropriate variations from the procedures, both as to reactants and reaction conditions and techniques.

[0273] Unless otherwise stated, 1 H NMR spectra were recorded at 400 MHz (megahertz) and chemical shifts are reported in ppm. The following abbreviations are used: s = singlet; brs = broad singlet; d = doublet; dd = double doublet; dt = double triplet; t = triplet, tt = triplet, q = quartet, quin = quintuplet, sept = septet; m = multiplet.

[0274] Example 1: This example illustrates the preparation of 5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)ethyl]-2-methyl-pyrimidine-4-carboxamide (compound 1.1 of Table T1). [ka] a) Preparation of 5-bromo-N-[2-(2,4-dichlorophenyl)ethyl]-2-methyl-pyrimidine-4-carboxamide [ka] A mixture of 5-bromo-2-methyl-pyrimidine-4-carboxylic acid (0.6 g, 3 mmol), 2-(2,4-dichlorophenyl)ethylamine (0.6 g, 3 mmol), T3P (50% in ethyl acetate, 2 mL, 3 mmol) and triethylamine (2 mL, 20 mmol) in acetonitrile (8 mL) was stirred at room temperature for 2 h. The reaction mixture was then diluted with water and the precipitate was filtered and dried under reduced pressure to give 5-bromo-N-[2-(2,4-dichlorophenyl)ethyl]-2-methyl-pyrimidine-4-carboxamide as an off-white solid, which was used directly in the next step without further purification. 1 H NMR (400MHz, dimethylsulfoxide-d6) δ ppm 8.81(t,1H), 8.51(s,1H), 7.55(d,1H), 7.29(d,1H), 7.26-7.19(m,2H), 6.85(d,1H), 6.69-6.74(m,2H), 3.49-3.37(m,2H), 2.85(t,2H), 2.66(s,3H), 1.87-1.94(m,1H), 0.99-0.90(m,2H), 0.69-0.63(m,2H)

[0275] b) Preparation of 5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)ethyl]-2-methyl-pyrimidine-4-carboxamide [ka] N-benzyl-N'-(2-methyl-1-naphthyl)oxamide (0.05 g, 0.15 mmol), potassium phosphate (0.3 g, 1.5 mmol) and copper(I) bromide (6 mg, 0.04 mmol) were added to a solution of 5-bromo-N-[2-(2,4-dichlorophenyl)ethyl]-2-methyl-pyrimidine-4-carboxamide (0.3 g, 0.77 mmol) and 3-cyclopropylphenol (0.14 g, 0.93 mmol) in dimethylsulfoxide (3 mL). The reaction mixture was stirred at 120° C. for 3 hours. The reaction mixture was then cooled to room temperature. The reaction medium was diluted with water and extracted with ethyl acetate. The organic layer was then washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The crude residue obtained was purified by chromatography on silica gel (cyclohexane / ethyl acetate) to give 5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)ethyl]-2-methyl-pyrimidine-4-carboxamide (94 mg, 0.21 mmol) as an amorphous solid. 1 H NMR (400MHz, dimethylsulfoxide-d6) δ ppm 8.81(t,1H), 8.51(s,1H), 7.55(d,1H), 7.29(d,1H), 7.26-7.19(m,2H), 6.85(d,1H), 6.69-6.74(m,2H), 3.49-3.37(m,2H), 2.85(t,2H), 2.66(s,3H), 1.87-1.94(m,1H), 0.99-0.90(m,2H), 0.69-0.63(m,2H) LCMS (Method D): Retention time 4.05 min, m / z 442 (M+H)

[0276] Example 2: This example illustrates the preparation of 5-bromo-N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]-2-methyl-pyrimidine-4-carboxamide (compound 1.2, Table T1). [ka] a) Preparation of 5-bromo-N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]-2-methyl-pyrimidine-4-carboxamide [ka] A mixture of 5-bromo-2-methyl-pyrimidine-4-carboxylic acid (0.6 g, 3 mmol), 2-(2,4-dichlorophenyl)-2-fluoro-ethanamine (0.7 g, 3 mmol), triethylamine (2 mL, 20 mmol) and T3P (50% by weight) in ethyl acetate (2 mL, 3 mmol) was stirred in acetonitrile (8 mL) at ambient temperature for 2 hours. The reaction mixture was then diluted with water to give a white solid, which was filtered, washed with water and dried under reduced pressure to give 5-bromo-N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]-2-methyl-pyrimidine-4-carboxamide as an off-white solid, which was used directly in the next step without further purification. 1 H NMR (400MHz, dimethylsulfoxide-d6) δ ppm 9.19(t,1H), 9.00(s,1H), 7.76-7.68(m,1H), 7.60(d,1H), 7.58-7.52(m,1H), 6.04-5.90(m,1H), 3.86-3.69(m,2H), 2.64(s,3H) 19 F NMR (377MHz, dimethylsulfoxide-d6) δ ppm-183.60 (s, 1F)

[0277] b) Preparation of 5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)ethyl]-2-methyl-pyrimidine-4-carboxamide [ka] To a solution of 5-bromo-N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]-2-methyl-pyrimidine-4-carboxamide (0.3 g, 0.7 mmol) and 3-cyclopropylphenol (0.125 g, 0.84 mmol) in DMSO (2.8 mL) was added N-benzyl-N'-(2-methyl-1-naphthyl)oxamide (0.045 g, 0.14 mmol), K3PO4 (0.30 g, 1.4 mmol) and copper(I) bromide (0.005 g, 0.035 mmol). The resulting reaction mixture was stirred at 120° C. for 2.5 hours. After removing the heat source, the contents were allowed to reach room temperature and diluted with water. The aqueous layer was extracted three times with ethyl acetate and the combined total organic layers were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude mass was purified by flash chromatography (cyclohexane / ethyl acetate) to give 5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]-2-methyl-pyrimidine-4-carboxamide as a solid. 1 H NMR (400MHz, dimethylsulfoxide-d6) δ ppm 9.00(t,1H), 8.44(s,1H), 7.60-7.58(m,1H) 7.44(d,1H), 7.33(dd,1H), 7.16(t,1H), 6.79(d,1H), 6.67-6.64(m,2H), 5.88-5.74(m,1H), 3.69-3.59(m,2H), 2.60(s,3H), 1.86-1.86(m,1H), 0.93-0.82(m,2H) 0.64-0.55(m,2H) 19 F NMR (377MHz, dimethylsulfoxide-d6) δ ppm-183.51 (s, 1F) LCMS (Method D): Retention time 3.93 min, m / z 460 (M+H)

[0278] Example 3: This example illustrates the preparation of 5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]-3-methyl-pyridazine-4-carboxamide (compound 2.1 of Table T2). [ka] a) Preparation of 5-bromo-4-(3-cyclopropylphenoxy)-1H-pyridazin-6-one [ka] A mixture of 4,5-dibromopyridazin-3-ol (10 g, 37.4 mmol), 3-cyclopropylphenol (41.16 mmol) was placed in dimethylsulfoxide (80 mL) in a round-bottom flask. Dry cesium carbonate (93.5 mmol) was added and the flask was purged with a stream of nitrogen for 10 min. Copper(I) iodide (1.87 mmol) and N,N-dimethylglycine (5.61 mmol) were added and the flask was purged again with nitrogen for 5 min. The reaction mixture was then heated at 110° C. for 5 h. The progress of the reaction was monitored by TLC and LCMS. The mixture was diluted with ethyl acetate, quenched with water, and extracted with ethyl acetate. The organic layer was washed with water, brine, dried over sodium sulfate, filtered, and evaporated under reduced pressure to give a residue that was purified by silica gel chromatography (cyclohexane / ethyl acetate). A solid was obtained and washed with tert-butyl methyl ether to give pure 5-bromo-4-(3-cyclopropylphenoxy)-1H-pyridazin-6-one (6.1 g, 18.7 mmol) as a white solid. 1 H NMR(400MHz,CDCl3)δ ppm 11.82(br s,1H)7.44(s,1H)7.34(t,1H)7.03(d,1H)6.89(ddd,1H)6.83(t,1H)1.97-1.90(m,1H)1.08-1.02(m,2H)0.77-0.71(m,2H) LCMS (Method B-SQD): Retention time 1.02 min, m / z 307,309 (M+H)

[0279] b) Preparation of methyl 4-(3-cyclopropylphenoxy)-6-oxo-1H-pyridazine-5-carboxylate [ka] A 50 ml autoclave vessel was charged with 5-bromo-4-(3-cyclopropylphenoxy)-1H-pyridazin-6-one (3.0 g, 9.8 mmol), triethylamine (20 mmol), methanol (30 mL), Pd(dppf)Cl2.CH2Cl2 (0.98 mmol). The reactor was flushed twice with carbon monoxide and charged to 15 bar. The reaction mixture was heated to 90° C. After 5 hours, the autoclave was cooled to 25° C., the pressure was released and flushed twice with nitrogen. The progress of the reaction was monitored by LCMS. The reaction mass was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to give the crude product which was washed with pentane to give methyl 4-(3-cyclopropylphenoxy)-6-oxo-1H-pyridazine-5-carboxylate (1.4 g, 45%). The resulting residue was pure enough for the next step. 1 H NMR(400MHz,CDCl3)δ ppm 11.34-11.16(m,1H)7.56(s,1H)7.32(t,1H)7.01(d,1H)6.90(ddd,1H)6.8 1(t,1H)3.88(s,3H)1.96-1.89(m,1H)0.98-1.11(m,2H)0.78-0.68(m,2H) LCMS (Method B-QDQ): Retention time 0.98 min, m / z 287(M+H)

[0280] c) Preparation of methyl 3-chloro-5-(3-cyclopropylphenoxy)pyridazine-4-carboxylate [ka] To methyl 4-(3-cyclopropylphenoxy)-6-oxo-1H-pyridazine-5-carboxylate (0.8 g, 2.65 mmol) in a round bottom flask was added phosphorus oxychloride (53.11 mmol) slowly under stirring. The reaction mixture was heated at 75° C. for 2 hours. The resulting yellow oil was allowed to cool to room temperature, diluted with ethyl acetate and slowly poured into water (50 ml) in an Erlenmeyer flask with gentle shaking. The organic layer was separated from the aqueous layer, washed with water, dried over sodium sulfate and evaporated to give methyl 3-chloro-5-(3-cyclopropylphenoxy)pyridazine-4-carboxylate (750 mg, 85% purity, 78%), which was used directly in the next step without further purification. LCMS (Method B-SQD): Retention time 1.08 min, m / z 305,307 (M+H)

[0281] d) Preparation of methyl 5-(3-cyclopropylphenoxy)-3-methyl-pyridazine-4-carboxylate [ka] To a solution of methyl 3-chloro-5-(3-cyclopropylphenoxy)pyridazine-4-carboxylate (1.75 g, 5.74 mmol) in 2-methyltetrahydrofuran (35 mL) was added potassium carbonate (11.5 mmol), 1,1'-bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane complex Pd(dppf)Cl2.CH2Cl2 (0.287 mmol) and trimethylboroxine (11.5 mmol). The reaction mixture was stirred at 95 °C for 3 h. Progress was monitored by TLC and LCMS. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and evaporated to give the crude product, which was purified by silica gel chromatography (cyclohexane / ethyl acetate) to give methyl 5-(3-cyclopropylphenoxy)-3-methyl-pyridazine-4-carboxylate (1.2 g, 4.13 mmol). 1H NMR(400MHz,CDCl3)δ ppm 8.71(s,1H)7.33(t,1H)7.02(d,1H)6.89(ddd,1H)6.81(t,1H)3.97(s,3H)2.76 (s,3H)2.00-1.84(m,1H)1.09-0.97(m,2H)0.75-0.69(m,1H)0.78-0.66(m,1H) LCMS (Method B-SQD): Retention time 1.07 min, m / z 285(M+H)

[0282] e) Preparation of 5-(3-cyclopropylphenoxy)-3-methyl-pyridazine-4-carboxylic acid [ka] To a stirred solution of methyl 5-(3-cyclopropylphenoxy)-3-methyl-pyridazine-4-carboxylate (0.65 g, 2.3 mmol) in 3:1 tetrahydrofuran / water (20 mL) was added barium hydroxide octahydrate (6.9 mmol). The mixture was stirred at room temperature for 4 h. The progress of the reaction was monitored by TLC and LCMS. The reaction mixture was acidified with 1N HCl and extracted twice with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure to give 5-(3-cyclopropylphenoxy)-3-methyl-pyridazine-4-carboxylic acid (0.42 g, 1.5 mmol). LCMS (Method B-QDA): Retention time 0.18 min, m / z 271 (M+H)

[0283] f) Preparation of 5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]-3-methyl-pyridazine-4-carboxamide [ka] To a mixture of 5-(3-cyclopropylphenoxy)-3-methyl-pyridazine-4-carboxylic acid (125 mg, 0.39 mmol, 85% purity) and 2-(2,4-dichlorophenyl)-2-fluoro-ethanamine (0.47 mmol) in EtOAc (5 mL / mmol) was added Et3N (0.864 mmol) and T3P (50% by weight in EtOAc) (1.179 mmol) at room temperature and the reaction mixture was stirred at room temperature for 16 h. The progress of the reaction was monitored by LCMS. The reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with saturated solutions of sodium bicarbonate and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to give the crude product. The crude material was purified by silica gel chromatography (cyclohexane / ethyl acetate) followed by preparative HPLC to give 5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]-3-methyl-pyridazine-4-carboxamide (41 mg, 0.085 mmol). 1 H NMR(400MHz,CDCl3)δ ppm 8.66(s,1H)7.42-7.33(m,3H)7.16(dd,1H)7.04(d,1H)6.87(d,1H)6.79(t,1H)6.54(br s,1H)6.02-5.90(m,1H)4.08-4.19(m,1H)3.92-3.80(m,1H)2.74(s,3H)1.93(tt,1H)1.10-0.98(m,2H)0.77-0.68(m,2H) LCMS (Method B-SQD): Retention time 1.12 min, m / z 460 (M+H)

[0284] Example 4: This example illustrates the preparation of 3-chloro-5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]pyridazine-4-carboxamide (compound 2.2 of Table T2). [ka] Methyl 3-chloro-5-(3-cyclopropylphenoxy)pyridazine-4-carboxylate, prepared in Example 3, is used. a) Preparation of 3-chloro-5-(3-cyclopropylphenoxy)pyridazine-4-carboxylic acid [ka] Barium hydroxide octahydrate (861 mg, 4.93 mmol) was added to a stirred solution of methyl 3-chloro-5-(3-cyclopropylphenoxy)pyridazine-4-carboxylate (500 mg, 1.64 mmol) in a 3:1 mixture of tetrahydrofuran / water (15 mL). The mixture was stirred at room temperature for 4 h. The progress of the reaction was monitored by TLC and LCMS. The pH of the reaction mixture was adjusted to 1 with 1N hydrochloric acid and the desired organic material was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 3-chloro-5-(3-cyclopropylphenoxy)pyridazine-4-carboxylic acid (400 mg, 1.31 mmol). The resulting residue was pure enough for the next step. LCMS (Method B-QDA): Retention time 0.16 min, m / z 291,293 (M+H)

[0285] b) Preparation of 3-chloro-5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]pyridazine-4-carboxamide: [ka] In a round bottom flask, N,N-diisopropylethylamine (204 mg, 1.55 mmol) and HATU (223 mg, 0.568 mmol) were added to 3-chloro-5-(3-cyclopropylphenoxy)pyridazine-4-carboxylic acid (150 mg, 0.516 mmol) and 2-(2,4-dichlorophenyl)-2-fluoro-ethanamine (0.619 mmol) in dimethylformamide (1.5 mL). The resulting pale yellow solution was stirred at room temperature for 16 hours. The progress of the reaction was checked by TLC and LCMS. The reaction mass was diluted with water and extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate solution, water, brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to give the crude material which was purified by silica gel chromatography (cyclohexane / ethyl acetate) followed by preparative TLC purification (cyclohexane / dichloromethane) to give 3-chloro-5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]pyridazine-4-carboxamide (100 mg, 0.21 mmol). 1 H NMR(400MHz,CDCl3)δ ppm 8.66(s,1H)7.44-7.34(m,3H)7.17(dd,1H)7.07(d,1H)6.91(ddd,1H)6.83(t,1H)6.75(br s,1H)6.03-5.91(dq,1H)4.21-4.11(m,1H)3.88-3.75(m,1H)1.96-1.88(m,1H)1.11-0.97(m,2H)0.76-0.69(m,2H) LCMS (Method B-QDA): Retention time 1.18 min, m / z 480 (M+H)

[0286] Example 5: This example illustrates the preparation of 5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]-3-ethyl-pyridazine-4-carboxamide (compound 2.3 of Table T2). [ka] Methyl 3-chloro-5-(3-cyclopropylphenoxy)pyridazine-4-carboxylate, prepared in Example 3, is used. a) Preparation of methyl 5-(3-cyclopropylphenoxy)-3-ethyl-pyridazine-4-carboxylate [ka] To a solution of methyl 3-chloro-5-(3-cyclopropylphenoxy)pyridazine-4-carboxylate (1.0 g, 3.3 mmol) in 2-methyltetrahydrofuran (20 mL) was added potassium carbonate (0.91 g, 6.6 mmol), Pd(dppf)Cl2.CH2Cl2 (0.32 mmol) and ethylboronic acid (0.73 g, 9.8 mmol). The reaction mixture was stirred at 95 °C for 16 h. The progress of the reaction was checked by TLC and LCMS. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and evaporated to give a crude residue which was purified by silica gel chromatography (cyclohexane / ethyl acetate) to give methyl 5-(3-cyclopropylphenoxy)-3-ethyl-pyridazine-4-carboxylate (250 mg, 0.84 mmol). 1 H NMR(400MHz,CDCl3)δ ppm 8.71(s,1H)7.33(t,1H)7.03(d,1H)6.89(d,1H)6.81(t,1H)3.98(s,3H)3.04( q,2H)1.96-1.88(m,1H)1.46-1.40(m,3H)1.09-0.97(m,2H)0.77-0.68(m,2H) LCMS (Method B-SQD): Retention time 1.12 min, m / z 299(M+H)

[0287] b) Preparation of 5-(3-cyclopropylphenoxy)-3-ethyl-pyridazine-4-carboxylic acid [ka] To a stirred solution of methyl 5-(3-cyclopropylphenoxy)-3-ethyl-pyridazine-4-carboxylate (250 mg, 0.83 mmol) in a binary mixture of tetrahydrofuran / water 3:1 (7.5 mL) was added barium hydroxide octahydrate (2.51 mmol). The mixture was sonicated at room temperature for 2.5 hours. The reaction progress was confirmed by TLC and LCMS. The reaction mixture was extracted with ethyl acetate, washed with water, and then the pH of the aqueous layer was adjusted to 1 with 1N HCl. The desired material was extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give 5-(3-cyclopropylphenoxy)-3-ethyl-pyridazine-4-carboxylic acid (160 mg, 60% yield). 1 H NMR(400MHz,CDCl3)δ ppm 8.63(s,1H)7.32-7.27(m,1H)7.01(d,1H)6.93-6.86(m,1H)6.82(s,1H)3.15(br s,2H)1.89(s,1H)1.42(br s,3H)1.04-0.96(m,2H)0.73-0.65(m,2H)

[0288] c) Preparation of 5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]-3-ethyl-pyridazine-4-carboxamide [ka] A round bottom flask was charged with a mixture of 5-(3-cyclopropylphenoxy)-3-ethyl-pyridazine-4-carboxylic acid (125 mg, 0.439 mmol) and 2-(2,4-dichlorophenyl)-2-fluoro-ethanamine (110 mg, 0.527 mmol) in ethyl acetate (2.2 mL). To this was added triethylamine (0.26 mL, 1.760 mmol) followed by T3P (50% in ethyl acetate, 0.78 mL, 1.32 mmol). The reaction mixture was stirred at room temperature for 16 hours. The progress of the reaction was monitored by LCMS. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with a saturated solution of sodium bicarbonate and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to give the crude product. The crude was then purified by silica gel chromatography (cyclohexane / ethyl acetate) to give 5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]-3-ethyl-pyridazine-4-carboxamide (73 mg, 0.150 mmol). 1 H NMR(400MHz,CDCl3)δ ppm 8.61(s,1H),7.45-7.32(m,3H),7.20-7.15(m,1H),7.04(d,1H),6.91-6.83(m,1H),6.83-6.72(m,2H),6.03-5.91(dq,1H) ,4.22-4.09(m,1H),3.94-3.80(m,1H),3.00(q,2H),1.97-1.88(m,1H),1.38(t,3H),1.08-1.00(m,2H),0.78-0.67(m,2H) LCMS (Method C): Retention time 1.96 min, m / z 476 (M+H)

[0289] Example 6: This example illustrates the preparation of 5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]-3-isopropoxy-pyridazine-4-carboxamide (compound 2.4 of Table T2). [ka] Methyl 4-(3-cyclopropylphenoxy)-6-oxo-1H-pyridazine-5-carboxylate, prepared in Example 3, is used. a) Preparation of methyl 5-(3-cyclopropylphenoxy)-3-isopropoxy-pyridazine-4-carboxylate [ka] A two-necked round bottom flask fitted with a reflux condenser was charged with methyl 4-(3-cyclopropylphenoxy)-6-oxo-1H-pyridazine-5-carboxylate (300 mg, 1.048 mmol) and silver carbonate (590 mg, 2.1 mmol) in toluene (7.5 mL). The reaction mixture was heated at 100° C. and stirred vigorously. To this, 2-iodopropane (534 mg, 3.14 mmol) was added slowly at 100° C. and stirred for 2 hours. The progress of the reaction was checked by TLC and LCMS. After completion, the reaction mixture was diluted with ethyl acetate and water. The desired material was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to give a crude residue which was purified by silica gel chromatography (cyclohexane / ethyl acetate) to give methyl 5-(3-cyclopropylphenoxy)-3-isopropoxy-pyridazine-4-carboxylate (200 mg, 0.61 mmol). 1 H NMR(400MHz,CDCl3)δ ppm 8.46(s,1H)7.32-7.25(m,1H)6.98(d,1H)6.87(ddd,1H)6.79(t,1H)5.66-5.57(m,1H )3.91(s,3H)1.94-1.86(m,1H)1.45-1.40(d,6H)1.07-0.94(m,2H)0.76-0.64(m,2H) LCMS (Method B-QDA): Retention time 1.20 min, m / z 329 (M+H)

[0290] b) Preparation of 5-(3-cyclopropylphenoxy)-3-isopropoxy-pyridazine-4-carboxylic acid [ka] To a stirred solution of methyl 5-(3-cyclopropylphenoxy)-3-isopropoxy-pyridazine-4-carboxylate (250 mg, 0.7613 mmol) in a 3:1 tetrahydrofuran / water (7.5 mL) mixture was added barium hydroxide octahydrate (400 mg, 2.284 mmol) and the mixture was stirred at room temperature for 4 h. The progress of the reaction was monitored by TLC and LCMS. The desired organic material was extracted with ethyl acetate and washed with water. The pH of the aqueous layer was adjusted to 1 with 1N HCl and the aqueous solution was extracted twice with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 5-(3-cyclopropylphenoxy)-3-isopropoxy-pyridazine-4-carboxylic acid (170 mg, 67% yield). LCMS (Method B-QDA): Retention time 1.04 min, m / z 315(M+H)

[0291] c) Preparation of 5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]-3-isopropoxy-pyridazine-4-carboxamide [ka] To a mixture of 5-(3-cyclopropylphenoxy)-3-isopropoxy-pyridazine-4-carboxylic acid (200 mg, 0.636 mmol) and 2-(2,4-dichlorophenyl)-2-fluoro-ethanamine (0.16 g, 0.763 mmol) in ethyl acetate (3.2 mL) was added triethylamine (0.37 mL, 2.55 mmol) followed by T3P (50% by weight in ethyl acetate, 1.12 mL, 1.9 mmol). The reaction mixture was stirred at room temperature for 16 hours. The progress of the reaction was monitored by TLC and LCMS. The reaction mixture was diluted with water and extracted twice with ethyl acetate. The organic layer was washed using a saturated solution of sodium bicarbonate and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to give a crude residue which was purified by silica gel chromatography (cyclohexane / ethyl acetate) followed by preparative HPLC to give pure 5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]-3-isopropoxy-pyridazine-4-carboxamide (67 mg, 0.126 mmol). 1 H NMR(400MHz,CDCl3)δ ppm 8.46(s,1H)7.45(d,1H)7.41(s,1H)7.33-7.28(m,1H)7.27-7.21(m,1H)7.00(d,1H)6.90-6.83(m,1H)6.79(t,1H)6.60(br s,1H)6.13-5.84-6.13(m,1H)5.66(dt,1H)4.25-4.13(m,1H)3.75-3.59(m, 1H)1.87-1.94(m,1H)1.42-1.50(m,6H)1.08-0.95(m,2H)0.77-0.65(m,2H) LCMS (Method B-QDA): Retention time 1.24 min, m / z 504 (M+H)

[0292] Example 7: This example illustrates the preparation of 5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]-3-(2-methylallyloxy)pyridazine-4-carboxamide (compound 2.5 of Table T2). [ka] Methyl 4-(3-cyclopropylphenoxy)-6-oxo-1H-pyridazine-5-carboxylate, prepared in Example 3, is used. a) Preparation of methyl 5-(3-cyclopropylphenoxy)-3-(2-methylallyloxy)pyridazine-4-carboxylate [ka] A two-necked round bottom flask fitted with a reflux condenser was charged with methyl 4-(3-cyclopropylphenoxy)-6-oxo-1H-pyridazine-5-carboxylate (0.2 g, 0.69 mmol) and silver carbonate (1.39 mmol) in toluene (8 mL). The resulting mixture was heated at 100° C. and stirred vigorously. To this, 3-bromo-2-methyl-prop-1-ene (2.09 mmol) was added slowly at 100° C. and stirred for 5 hours. The progress of the reaction was monitored by TLC and LCMS. The reaction mixture was diluted with ethyl acetate and water and extracted into ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to give the crude material which was purified by silica gel chromatography (cyclohexane / ethyl acetate) to give methyl 5-(3-cyclopropylphenoxy)-3-(2-methylallyloxy)pyridazine-4-carboxylate (72 mg, 0.21 mmol). 1 H NMR(400MHz,CDCl3)δ ppm 8.51(s,1H)7.32-7.26(m,1H)7.00(d,1H)6.88(ddd,1H)6.80(t,1H)5.11(s,1H)5.05 -4.97(m,3H)3.92(s,3H)1.90(tt,1H)1.85(s,3H)1.10-0.93(m,2H)0.78-0.63(m,2H) LCMS (Method B-QDA): Retention time 1.21 min, m / z 341 (M+H)

[0293] b) Preparation of 5-(3-cyclopropylphenoxy)-3-(2-methylallyloxy)pyridazine-4-carboxylic acid [ka] To a stirred solution of methyl 5-(3-cyclopropylphenoxy)-3-(2-methylallyloxy)pyridazine-4-carboxylate (250 mg, 0.7344 mmol) in a binary mixture of tetrahydrofuran / water 3:1 (7.5 mL) was added barium hydroxide octahydrate (2.2 mmol). The resulting mixture was stirred at room temperature for 4 hours. The progress of the reaction was confirmed by TLC and LCMS. The reaction mixture was extracted with ethyl acetate, washed with water, and then the pH of the aqueous layer was adjusted to 1 with 1N HCl. The desired material was extracted twice with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 5-(3-cyclopropylphenoxy)-3-(2-methylallyloxy)pyridazine-4-carboxylic acid (200 mg, 0.58 mmol). 1 H NMR (400MHz, dimethylsulfoxide-d6) δ ppm 14.12 (br s, 1H) 8.55 (s, 1H) 7.34 (t, 1H) 7.03 (d, 1H) 6.98-6.92 (m, 2H) 5.08 (s, 1H) 5.03-4.94 (m, 3H) 1.97 (s, 1H) 1.79 (s, 3H) 1.04-0.91 (m, 2H) 0.72 (dd, 2H)

[0294] c) Preparation of 5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]-3-(2-methylallyloxy)pyridazine-4-carboxamide [ka] To a mixture of 5-(3-cyclopropylphenoxy)-3-(2-methylallyloxy)pyridazine-4-carboxylic acid (150 mg, 0.4596 mmol) and 2-(2,4-dichlorophenyl)-2-fluoro-ethanamine (877.3 g, 0.5515 mmol) in ethyl acetate (2.3 mL) was added triethylamine (0.27 mL, 1.84 mmol) followed by T3P (50% by weight in EtOAc, 0.81 mL, 1.379 mmol). The reaction mixture was stirred at room temperature for 16 h. The progress of the reaction was followed by TLC and LCMS. The reaction mixture was diluted with water and extracted twice with ethyl acetate. The organic layer was washed with saturated solutions of sodium bicarbonate and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to give a crude residue. The residue was purified by silica gel chromatography (cyclohexane / ethyl acetate) to give an off-white solid, which was further purified by preparative HPLC to give pure 5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]-3-(2-methylallyloxy)pyridazine-4-carboxamide as a white solid (110 mg, 0.20 mmol). 1 H NMR(400MHz,CDCl3)δ ppm 8.49(s,1H)7.42(d,1H)7.39-7.38(m,1H)7.34-7.34(m,2H)7.20(dd,1H)7.01(d,1H)6.86(dd,1H)6.79(t,1H)6.48(br s,1H)6.03-5.79(m,1H)5.12(s,1H)5.05-5.00(m,3H)4.25-3.68(m,1H)1.92(m,1H)1.86(s,3H)1.06-0.97(m,2H)0.74-0.67(m,2H) LCMS (Method B-QDA): Retention time 1.28 min, m / z 516 (M+H)

[0295] Example 8: This example illustrates the preparation of 3-(2-cyclopropylethynyl)-5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]pyridazine-4-carboxamide (compound 2.6 of Table T2). [ka] Methyl 3-chloro-5-(3-cyclopropylphenoxy)pyridazine-4-carboxylate, prepared in Example 3, is used. a) Preparation of methyl 3-(2-cyclopropylethynyl)-5-(3-cyclopropylphenoxy)pyridazine-4-carboxylate [ka] In a microwave vial, a solution of methyl 3-chloro-5-(3-cyclopropylphenoxy)pyridazine-4-carboxylate (0.2 g, 0.656 mmol) in acetonitrile (2 mL) was purged with nitrogen. To this was added XPhos Pd G3 (57.7 mg, 0.066 mmol) and cesium carbonate (0.99 g, 3.06 mmol) and the mixture was purged again with nitrogen before adding cyclopropylacetylene (0.15 mL, 1.8 mmol). The resulting mixture was irradiated at 90° C. for 1 h. The progress of the reaction was monitored by TLC and LCMS. The reaction mixture was then diluted with water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to give the crude product. The crude mixture was purified by silica gel chromatography (cyclohexane / ethyl acetate) to give methyl 3-(2-cyclopropylethynyl)-5-(3-cyclopropylphenoxy)pyridazine-4-carboxylate (130 mg, 0.37 mmol). 1 H NMR(400MHz,CDCl3)δ ppm 8.70(s,1H)7.33(t,1H)7.05-6.99(m,1H)6.89(ddd,1H)6.83-6.78(m,1H)3.97 (s,3H)1.97-1.87(m,1H)1.60-1.53(m,1H)1.07-0.92(m,6H)0.83-0.61(m,2H) LCMS (Method B-QDA): Retention time 1.17 min, m / z 335(M+H)

[0296] b) Preparation of 3-(2-cyclopropylethynyl)-5-(3-cyclopropylphenoxy)pyridazine-4-carboxylic acid [ka] To a stirred solution of methyl 3-(2-cyclopropylethynyl)-5-(3-cyclopropylphenoxy)pyridazine-4-carboxylate (400 mg, 1.196 mmol) in tetrahydrofuran / water 3:1 (12 mL) was added barium hydroxide octahydrate (7.177 mmol). The mixture was stirred in a sonicator at room temperature for 5 hours. The reaction progress was monitored by TLC and LCMS. The pH of the reaction mixture was adjusted to 1 using 1N HCl. The desired material was extracted twice with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give crude 3-(2-cyclopropylethynyl)-5-(3-cyclopropylphenoxy)pyridazine-4-carboxylic acid (350 mg, 1 mmol), which was used directly in the next step without further purification. LCMS (Method B-QDA): Retention time 0.98 min, m / z 321(M+H)

[0297] c) 3-(2-cyclopropylethynyl)-5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]pyridazine-4-carboxamide [ka] To a mixture of 3-(2-cyclopropylethynyl)-5-(3-cyclopropylphenoxy)pyridazine-4-carboxylic acid (280 mg, 0.699 mmol, 80% pure), 2-(2,4-dichlorophenyl)-2-fluoro-ethanamine (0.839 mmol) in dimethylformamide (2.8 mL) was added N-ethyl-N-isopropyl-propan-2-amine (1.748 mmol) followed by HATU (0.769 mmol). The resulting pale yellow solution was stirred at room temperature for 2 h. The progress of the reaction was followed by TLC and LCMS. The reaction mixture was diluted with water and extracted twice with ethyl acetate. The organic layer was washed with saturated solutions of sodium bicarbonate and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to give the crude product. The crude material was purified by silica gel chromatography (cyclohexane / ethyl acetate) to give an off-white solid, which was further purified by preparative HPLC to give pure 3-(2-cyclopropylethynyl)-5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]pyridazine-4-carboxamide (0.055 g, 0.10 mmol). 1 H NMR(400MHz,CDCl3)δ ppm 8.67(s,1H)7.47-7.42(m,2H)7.35(t,1H)7.24(d,1H)7.04(d,1H)6.88(ddd,1H)6.80(t,1H)6.45(t,1H)6.12-5 .90(m,1H)4.30-4.18(m,1H)3.75-3.62(m,1H)1.93(s,1H)1.58-1.53(m,1H)1.07-0.96(m,6H)0.77-0.68(m,2H) LCMS (Method B-QDA): Retention time 1.27 min, m / z 510,512[M+H] +

[0298] Example 9: This example illustrates the preparation of 5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]-3-isopropenyl-pyridazine-4-carboxamide (compound 2.7 of Table T2). [ka] Methyl 3-chloro-5-(3-cyclopropylphenoxy)pyridazine-4-carboxylate, prepared in Example 3, is used. a) Preparation of methyl 5-(3-cyclopropylphenoxy)-3-isopropenyl-pyridazine-4-carboxylate [ka] A microwave vial was charged with methyl 3-chloro-5-(3-cyclopropylphenoxy)pyridazine-4-carboxylate (0.60 g, 1.96 mmol), 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (1.03 g, 5.90 mmol), cesium carbonate (2.56 g, 7.87 mmol) in 1,4-dioxane (6 mL) and water (0.98 mL). The reaction mixture was purged with argon for 10 minutes. Pd(dppf)Cl2.CH2Cl2 (0.48 g, 0.59 mmol) was added to the reaction mixture. The resulting reaction mixture was irradiated at 90 °C for 2 hours. The progress of the reaction was monitored by LCMS and TLC. After completion, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to give the crude compound. The crude residue obtained was purified by silica gel chromatography (cyclohexane / ethyl acetate) to give methyl 5-(3-cyclopropylphenoxy)-3-isopropenyl-pyridazine-4-carboxylate (280 mg, 0.90 mmol). 1 H NMR(400MHz,CDCl3)δ ppm 8.72(br s,1H)7.33(t,1H)7.03(d,1H)6.90(d,1H)6.82(t,1H)5.48(s,1H)5.34(s,1H) 3.91(s,3H)2.33(s,3H)1.87-1.96(m,1H)0.98-1.07(m,2H)0.69-0.74(m,2H)

[0299] b) Preparation of 5-(3-cyclopropylphenoxy)-3-isopropenyl-pyridazine-4-carboxylic acid [ka] In a single neck round bottom flask, methyl 5-(3-cyclopropylphenoxy)-3-isopropenyl-pyridazine-4-carboxylate (120 mg, 0.38 mmol) was stirred at room temperature in tetrahydrofuran (3.6 mL) and water (0.6 mL). Barium hydroxide (493 mg, 2.70 mmol) was then added and the mixture was stirred at room temperature for 24 h. The progress of the reaction was monitored by LCMS and TLC. After completion, the reaction mixture was diluted with water and extracted with tert-butyl methyl ether (10 mL) to remove non-polar impurities and the pH of the aqueous layer was adjusted to 4-5 using 2N HCl. The desired material was extracted with ethyl acetate (2x10 mL). The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to give 5-(3-cyclopropylphenoxy)-3-isopropenyl-pyridazine-4-carboxylic acid (110 mg, 0.33 mmol), which was used directly in the next step without further purification. LCMS (Method B-QDA): Retention time 0.95 min, m / z 297(M+H)

[0300] c) Preparation of 5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]-3-isopropenyl-pyridazine-4-carboxamide [ka] To a solution of 2-(2,4-dichlorophenyl)-2-fluoro-ethanamine (0.10 g, 0.52 mmol) and 5-(3-cyclopropylphenoxy)-3-isopropenyl-pyridazine-4-carboxylic acid (0.13 g, 0.43 mmol) in N,N-dimethylformamide (1.31 mL) was added HATU (0.25 g, 0.65 mmol) followed by N,N-diisopropylethylamine (0.23 mL, 1.31 mmol). The reaction mixture was stirred at room temperature for 2 hours. The progress of the reaction was monitored by TLC and LCMS. After completion, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude compound was purified using reverse phase column chromatography (water / acetonitrile 70%) to give 5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]-3-isopropenyl-pyridazine-4-carboxamide (124 mg, 0.26 mmol). 1 H NMR(400MHz,CDCl3)δ ppm 8.67(s,1H),7.42-7.38(m,2H)7.34(t,1H)7.18(dd,2.02Hz,1H)7.04(d,1H)6.88(dd,1H)6.80(t,1H)6.39(t,1H)5.96-5. 86(m,1H)5.46(d,2H)4.28-4.10(m,1H)3.77-3.61(m,1H)2.30(s,3H)1.97-1.97(m,1H)1.07-0.97(m,2H)0.76-0.67(m,2H) 19 F NMR(377MHz,CDCl3)δ ppm-188.74(s,1 F) LCMS (Method B-QDA): Retention time 1.24 min, m / z 486 (M+H)

[0301] Example 10: This example illustrates the preparation of 3-cyclopropyl-5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]pyridazine-4-carboxamide (compound 2.8 of Table T2). [ka] Methyl 3-chloro-5-(3-cyclopropylphenoxy)pyridazine-4-carboxylate, prepared in Example 3, is used. a) Preparation of methyl 3-cyclopropyl-5-(3-cyclopropylphenoxy)pyridazine-4-carboxylate [ka] A microwave vial was charged with methyl 3-chloro-5-(3-cyclopropylphenoxy)pyridazine-4-carboxylate (1.2 g, 3.9 mmol), cyclopropylboronic acid (0.68 g, 7.9 mmol), cesium carbonate (5.1 g, 16 mmol) in 1,4-dioxane (12 mL) and water (3.9 mL). The reaction mixture was purged with nitrogen for 10 minutes. To the reaction mixture was added Pd(dppf)Cl2·CH2Cl2 (0.32 g, 0.39 mmol) and the resulting reaction mixture was irradiated at 90 °C for 2 hours. The progress of the reaction was monitored by LCMS and TLC. After completion, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to give the crude compound. The crude residue obtained was purified by silica gel chromatography (cyclohexane / ethyl acetate) to give methyl 3-cyclopropyl-5-(3-cyclopropylphenoxy)pyridazine-4-carboxylate (330 mg, 1.06 mmol). LCMS (Method B-SQD): Retention time 1.13 min, m / z 311(M+H)

[0302] b) Preparation of 3-cyclopropyl-5-(3-cyclopropylphenoxy)pyridazine-4-carboxylic acid [ka] In a single neck round bottom flask, methyl 3-cyclopropyl-5-(3-cyclopropylphenoxy)pyridazine-4-carboxylate (200 mg, 0.64 mmol) in tetrahydrofuran (6 mL) was stirred at room temperature. To this was added barium hydroxide (822 mg, 4.51 mmol) and the mixture was stirred at room temperature for 8 hours. The progress of the reaction was monitored by TLC and LCMS. As the reaction was not complete, an additional amount of barium hydroxide (822 mg, 4.51 mmol) was added and the reaction mixture was stirred at room temperature for another 24 hours. After completion, the reaction mass was diluted with water and extracted with tert-butyl methyl ether (10 mL) to remove non-polar impurities and the pH of the aqueous layer was adjusted to 4-5 using 2N HCl. The desired material was extracted with ethyl acetate (2x10 mL). The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to give 3-cyclopropyl-5-(3-cyclopropylphenoxy)pyridazine-4-carboxylic acid (180 mg, 0.55 mmol), which was used directly in the next step without further purification. LCMS (Method B-QDA): Retention time 0.96 min, m / z 297(M+H)

[0303] c) Preparation of 3-cyclopropyl-5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]pyridazine-4-carboxamide [ka] To a solution of 2-(2,4-dichlorophenyl)-2-fluoro-ethanamine (0.12 g, 0.60 mmol) and 3-cyclopropyl-5-(3-cyclopropylphenoxy)pyridazine-4-carboxylic acid (181 mg, 0.55 mmol) in N,N-dimethylformamide (1.65 mL) was added HATU (0.31 g, 0.82 mmol) and N,N-diisopropylethylamine (0.33 mL, 1.92 mmol). The reaction mixture was stirred at room temperature for 2 hours. The reaction was monitored by TLC and LCMS. After completion, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude compound was purified using a reverse phase column (water / acetonitrile 70%) to give 3-cyclopropyl-5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]pyridazine-4-carboxamide (161 mg, 0.33 mmol). 1 H NMR(400MHz,CDCl3)δ ppm 8.53(s,1H)7.43-7.37(m,2H)7.32(t,1H)7.17(dd,1H)7.01(d,1H)6.84(dd,1H)6.77(t,1H)6.55(t,1H)6.07-5.87(m,1H)4.23-4.07 (m,1H)3.98-3.82(m,1H)2.14-2.03(m,1H)1.96-1.86(m,1H)1.45-1.34(m,2H)1.16-1.08(m,2H)1.08-0.96(m,2H)0.75-0.66(m,2H) 19 F NMR(377MHz,CDCl3)δ ppm-188.91(s,1 F) LCMS (Method B-SQD): Retention time 1.17 min, m / z 486 (M+H)

[0304] Example 11: This example illustrates the preparation of 5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]-3-isopropyl-pyridazine-4-carboxamide (compound 2.9 of Table T2). [ka] a) Preparation of methyl 5-(3-cyclopropylphenoxy)-3-isopropyl-pyridazine-4-carboxylate [ka] To a solution of methyl 5-(3-cyclopropylphenoxy)-3-isopropenyl-pyridazine-4-carboxylate (0.10 g, 0.32 mmol) in methanol (2 mL), anhydrous platinum oxide (11 mg, 0.048 mmol) was added and the reaction mixture was stirred under 1 atm of hydrogen for 1 h. The progress of the reaction was monitored by TLC and LCMS. After completion, the crude reaction mixture was directly filtered through a pad of Celite and washed with methanol. The filtrate was concentrated to give methyl 5-(3-cyclopropylphenoxy)-3-isopropyl-pyridazine-4-carboxylate as a crude product (100 mg, 79%), which was used directly in the next step without further purification. LCMS (Method B-QDA): Retention time 1.18 min, m / z 313(M+H)

[0305] b) Preparation of 5-(3-cyclopropylphenoxy)-3-isopropyl-pyridazine-4-carboxylic acid [ka] In a single neck round bottom flask, methyl 5-(3-cyclopropylphenoxy)-3-isopropyl-pyridazine-4-carboxylate (100 mg, 0.32 mmol) was stirred at room temperature in tetrahydrofuran (3 mL) and water (1 mL). Barium hydroxide (408 mg, 2.24 mmol) was added and the mixture was stirred at room temperature for 24 h. The progress of the reaction was monitored by LCMS and TLC. After completion, the reaction mixture was diluted with water and extracted with tert-butyl methyl ether (2x10 mL) to remove non-polar impurities and the pH of the aqueous layer was adjusted to 4-5 using 2N HCl. The desired material was extracted with ethyl acetate (2x10 mL). The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure to give 5-(3-cyclopropylphenoxy)-3-isopropyl-pyridazine-4-carboxylic acid (80 mg, 0.24 mmol), which was used directly in the next step without further purification. LCMS (Method B-QDA): Retention time 0.93 min, m / z 299 (M+H)

[0306] c) Preparation of 5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]-3-isopropyl-pyridazine-4-carboxamide [ka] To a solution of 2-(2,4-dichlorophenyl)-2-fluoro-ethanamine (50 mg, 0.24 mmol) and 5-(3-cyclopropylphenoxy)-3-isopropyl-pyridazine-4-carboxylic acid (60 mg, 0.20 mmol) in N,N-dimethylformamide (0.6 mL) was added HATU (0.11 g, 0.30 mmol) and N,N-diisopropylethylamine (0.1 mL, 0.60 mmol). The reaction mixture was stirred at room temperature for 2 hours. The progress of the reaction was monitored by TLC and LCMS. After completion, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude compound was purified using reverse phase chromatography (water / acetonitrile 70%) to give 5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]-3-isopropyl-pyridazine-4-carboxamide (52 mg, 0.1065 mmol). 1 H NMR(400MHz,CDCl3)δ ppm 8.64(s,1H),7.44-7.39(m,2H),7.37-7.30(m,1H),7.17(dd,1H),7.03(d,1H),6.90-6.84(m,1H),6.78(t,1H),6.32(t,1H),6.06-5.8 4(m,1H),4.23-4.10(m,1H),3.94-3.81(m,1H),3.22(quin,1H),1.95-1.88(m,1H),1.43(d,6H),1.09-0.97(m,2H),0.76-0.67(m,2H) 19 F NMR(377MHz,CDCl3)δ ppm-189.09(s,1 F) LCMS (Method B-QDA): Retention time 1.26 min, m / z 488 (M+H)

[0307] Example 12: This example illustrates the preparation of 5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]pyridazine-4-carboxamide (compound 2.10 of Table T2). [ka] 3-Chloro-5-(3-cyclopropylphenoxy)pyridazine-4-carboxylate, prepared in Example 3, is used. a) Preparation of methyl 5-(3-cyclopropylphenoxy)pyridazine-4-carboxylate [ka] A dry round bottom flask was charged with methyl 3-chloro-5-(3-cyclopropylphenoxy)pyridazine-4-carboxylate (0.34 g, 1.116 mmol) and methanol (6.8 mL). The reaction mixture was then degassed with nitrogen for 2 min. N,N-diethylethanamine (2.43 mmol, 0.34 mL) was added followed by 10% palladium on carbon (0.047 g, 0.223 mmol) under nitrogen atmosphere. The reaction was finally placed under 1 atm of hydrogen and stirred at room temperature for 3 h. The progress of the reaction was monitored by LCMS. The reaction mixture was filtered through a Celite path and the filtrate was concentrated to give the crude product. The crude product was purified by silica gel chromatography (cyclohexane / ethyl acetate) to give methyl 5-(3-cyclopropylphenoxy)pyridazine-4-carboxylate (150 mg, 0.50 mmol). 1 H NMR(400MHz,CDCl3)δ ppm 9.41(d,1H)8.85(d,1H)7.36(t,1H)7.06(d,1H)6.91(ddd,1H)6.83(t,1H)3.99(s,3H)2.01-1.86(m,1H)1.07-1.01(m,2H)0.76-0.70(m,2H)

[0308] b) Preparation of 5-(3-cyclopropylphenoxy)pyridazine-4-carboxylic acid [ka] To a stirred solution of methyl 5-(3-cyclopropylphenoxy)pyridazine-4-carboxylate (0.15 g, 0.55 mmol) in 3:1 THF / H2O (4.5 mL) was added barium hydroxide octahydrate (1.7 mmol) and the mixture was stirred at room temperature for 1.5 h. The reaction progress was monitored by TLC and LCMS. The reaction mixture was treated with 1N HCl and the desired material was extracted twice with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give crude 5-(3-cyclopropylphenoxy)pyridazine-4-carboxylic acid (110 mg, 0.41 mmol). 1 H NMR(400MHz,CDCl3)δ ppm 9.56(s,1H)8.87(s,1H)7.42-7.36(m,1H)7.10(d,1H)6.95(dd,1H)6.87(s,1H)1.95(s,1H)1.06(br,2H)0.77-0.72(m,2H)

[0309] c) Preparation of 5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]pyridazine-4-carboxamide [ka] To a mixture of 5-(3-cyclopropylphenoxy)pyridazine-4-carboxylic acid (0.11 g, 0.43 mmol) and 2-(2,4-dichlorophenyl)-2-fluoro-ethanamine (0.52 mmol) in ethyl acetate (8 mL / mmol) was added N-ethyl-N-isopropyl-propan-2-amine (1.3 mmol) followed by T3P (50% in ethyl acetate, 1.3 mmol). The resulting pale yellow solution was stirred at room temperature for 16 h. The progress of the reaction was monitored by TLC and LCMS. The reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with saturated solutions of sodium bicarbonate and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to give the crude product. The crude material was purified by silica gel chromatography (cyclohexane / ethyl acetate) to give 5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]pyridazine-4-carboxamide (150 mg, 0.34 mmol). 1 H NMR(400MHz,CDCl3)δ ppm 9.70(s,1H)8.81(s,1H)7.80-7.74(m,1H)7.46-7.37(m,3H)7.19(dd,1H)7.14(d,1H)6.94(d,1H)6.87(t,1H) 6.08-5.96(dq,1H)4.29-4.18(m,1H)3.86-3.74(m,1H)2.01-1.95(m,1H)1.14-1.06(m,2H)0.81-0.75(m,2H) LCMS (Method B-SQD): Retention time 1.23 min, m / z 446 (M+H)

[0310] Example 13: This example illustrates the preparation of 5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]-3-methoxy-pyridazine-4-carboxamide (compound 2.11 of Table T2). [ka] 5-Bromo-4-(3-cyclopropylphenoxy)-1H-pyridazin-6-one, prepared analogously to Example 3, procedure a), is used. a) Preparation of 4-bromo-5-(3-cyclopropylphenoxy)-3-methoxypyridazine [ka] In a sealed reaction tube, 5-bromo-4-(3-cyclopropylphenoxy)-1H-pyridazin-6-one (400 mg, 1.24 mmol), iodomethane (532 mg, 3.71 mmol) and silver(I) carbonate (414 mg, 1.48 mmol) were stirred in toluene (10 mL) under argon atmosphere at 100° C. for 2 h. The reaction progress was monitored by LCMS and TLC. The reaction mixture was then filtered through a path of Celite and evaporated to dryness to give a brown resin, which was purified by reverse phase chromatography (water / acetonitrile) to give 4-bromo-5-(3-cyclopropylphenoxy)-3-methoxy-pyridazine (44 mg, 0.137 mmol). LCMS (Method A): Retention time 1.06 min, m / z 321 (M+H)

[0311] b) Preparation of methyl 5-(3-cyclopropylphenoxy)-3-methoxypyridazine-4-carboxylate [ka] In a stainless steel autoclave, triethylamine (0.04 mL, 0.27 mmol) was added to a solution of 4-bromo-5-(3-cyclopropylphenoxy)-3-methoxy-pyridazine (59 mg, 0.175 mmol) in methanol (2.95 mL). To this, [Pd(BINAP)(allyl)Cl]Pd-176 (7.03 mg, 8.73 μmol) was added and the mixture was purged with a stream of argon for 5 min. The reaction mixture was then stirred at 80° C. under 5 bar of carbon monoxide for 16 h. The progress of the reaction was monitored by LCMS. The autoclave was finally purged and flushed with a stream of nitrogen. The reaction mixture was evaporated to dryness and directly purified by silica gel flash chromatography (cyclohexane / ethyl acetate) to give methyl 5-(3-cyclopropylphenoxy)-3-methoxy-pyridazine-4-carboxylate (43 mg, 0.143 mmol) as a colorless resin. 1 H NMR(400MHz,CDCl3)δ=8.52(s,1H),7.34-7.27(t,1H),6.99(d,1H),6.87(dd,1H),6.79( t,1H),4.19(s,3H),3.91(s,3H),1.96-1.84(m,1H),1.05-0.95(m,2H),0.73-0.66(m,2H) LCMS (Method A): Retention time 0.97 min, m / z 301 (M+H)

[0312] c) Preparation of 5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]-3-methoxypyridazine-4-carboxamide [ka] A round bottom flask was charged with methyl 5-(3-cyclopropylphenoxy)-3-methoxy-pyridazine-4-carboxylate (43 mg, 0.143 mmol) and a 3:1 binary solvent mixture of tetrahydrofuran and water (1.3 mL). To this, lithium hydroxide hydrate (7 mg, 0.163 mmol) was added and the mixture was stirred at room temperature for 19 hours. The progress of the reaction was monitored by LCMS. After completion, the reaction mixture was concentrated to give the crude mixture, which was used directly in the next step. LCMS (Method A): Retention time 0.70 min, m / z 284(MH)

[0313] d) Preparation of 5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]-3-methoxypyridazine-4-carboxamide [ka] To lithium 5-(3-cyclopropylphenoxy)-3-methoxy-pyridazine-4-carboxylate (46 mg, 0.134 mmol) in ethyl acetate (1.4 mL) was added 2-(2,4-dichlorophenyl)-2-fluoro-ethanamine (38.1 mg, 0.174 mmol) and N,N-diisopropylethylamine (118 μl, 0.669 mmol) followed by T3P (199 μl, 0.335 mmol). The reaction mixture was stirred at room temperature for 18 hours. The progress of the reaction was monitored by LCMS. The reaction mixture was quenched with saturated sodium bicarbonate solution, diluted with water and extracted with ethyl acetate (8 mL×3). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude residue obtained was purified by silica gel chromatography (cyclohexane / ethyl acetate) followed by RP chromatography to give 5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]-3-methoxy-pyridazine-4-carboxamide (14 mg, 22%). 1H NMR(400MHz,CDCl3)δ ppm 8.48(s,1H),7.44-7.37(m,2H),7.31(t,1H),7.20(dd,1H),7.00(d,1H),6.89-6.82(m,1H),6.78(t,1H),6.48(t,1H),6 .05-5.84(m,1H),4.19(s,3H),4.17-4.06(m,1H),3.85-3.69(m,1H),1.90(tt,1H),1.05-0.97(m,2H),0.74-0.66(m,2H) LCMS (Method B): Retention time 1.09 min, m / z 476 (M+H)

[0314] Example 14: This example illustrates the preparation of 5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)ethyl]-3-methoxy-pyridazine-4-carboxamide (compound 2.12 of Table T2). [ka] Lithium 5-(3-cyclopropylphenoxy)-3-methoxypyridazine-4-carboxylate as prepared in Example 13 is used. a) Preparation of 5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)ethyl]-3-methoxy-pyridazine-4-carboxamide [ka] To lithium 5-(3-cyclopropylphenoxy)-3-methoxy-pyridazine-4-carboxylic acid (27 mg, 0.09 mmol) in 2-methyltetrahydrofuran (1.1 mL) was added dimethylformamide (0.08 μl, 0.009 mmol) followed by oxalyl chloride (10 μl, 0.108 mmol). The reaction mixture was stirred at room temperature for 2 hours. After quenching an aliquot with methanol, the reaction progress was monitored by LCMS. Upon completion, the reaction mixture was evaporated to dryness. The resulting residue was dissolved in acetonitrile (1.1 mL) followed by addition of 2-(2,4-dichlorophenyl)-ethanamine (17 μl, 0.108 mmol) and potassium iodide (3.8 mg, 0.022 mmol). The reaction mixture was stirred at 70° C. for 5 hours. The reaction progress was monitored by LCMS. After completion, the reaction mixture was diluted with ethyl acetate (5 mL), quenched with saturated sodium bicarbonate solution and aqueous sodium thiosulfate solution (10%), and extracted with ethyl acetate (5 mL x 2). The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude residue obtained was purified by silica gel chromatography (cyclohexane / ethyl acetate) followed by reverse phase chromatography to give 5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)ethyl]-3-methoxy-pyridazine-4-carboxamide (13 mg, 0.0028 mmol). 1 H NMR (400MHz, dimethylsulfoxide-d6) δ ppm 8.68(t,1H), 8.47(s,1H), 7.52(d,1H), 7.38-7.28(m,2H), 7.10(dd,1H), 7.03(d,1H), 6.92-6.87(m,1H), 6.84(t,1H), 4.06(s,3H), 3.47(q,2H), 2.88(t,2H), 2.01-1.90(m,1H), 1.04-0.91(m,2H), 0.77-0.62(m,2H) LCMS (Method A): Retention time 1.09 min, m / z 458 (M+H)

[0315] Example 15: This example illustrates the preparation of N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]-5-(3-methoxyphenoxy)-3-methyl-pyridazine-4-carboxamide (compound 2.13 of Table T2). [ka] a) Preparation of 4-bromo-5-(3-methoxyphenoxy)pyridazin-3-ol [ka] In a vial, 4,5-dibromopyridazin-3(2H)-one (0.40 g, 1.50 mmol), cesium carbonate (1.23 g, 3.74 mmol) and 3-methoxyphenol (0.21 g, 0.18 mL, 1.65 mmol) were stirred in dry dimethylsulfoxide (4 mL) under argon for 5 minutes. To this was added copper(I) iodide (14.4 mg, 0.075 mmol) and N,N-dimethylglycine (24 mg, 0.225 mmol). The resulting brown mixture was stirred at 110° C. under argon for 4 hours. The mixture was diluted with ethyl acetate and water. The desired material was extracted with ethyl acetate (2×15 mL). The organic layer was washed with water, brine, dried over sodium sulfate, filtered and evaporated. The crude residue obtained was purified by silica gel chromatography (cyclohexane / ethyl acetate) to give 4-bromo-5-(3-methoxyphenoxy)pyridazin-3-ol (304 mg, 1.02 mmol) as a white solid. LCMS (Method A): Retention time 0.78 min, m / z 297(M+H)

[0316] b) Preparation of methyl 3-hydroxy-5-(3-methoxyphenoxy)pyridazine-4-carboxylate [ka] A glass autoclave was charged under argon with 4-bromo-5-(3-methoxyphenoxy)pyridazin-3-ol (304 mg, 1.02 mmol), triethylamine (0.156 g, 1.5348 mmol), [Pd(BINAP)(allyl)Cl] (41 mg, 0.051 mmol) and degassed methanol (10.2 mL). The autoclave was purged with carbon monoxide and charged to 5 bar. The reaction mixture was stirred at 80° C. for 18 h. The reaction progress was monitored by LCMS. After completion, the reaction mixture was concentrated to dryness and directly purified by silica gel chromatography (cyclohexane / ethyl acetate) to give methyl 3-hydroxy-5-(3-methoxyphenoxy)pyridazine-4-carboxylate (166 mg, 0.60 mmol). 1 H NMR(400MHz,CDCl3)δ ppm 10.64-10.38(m,1H),7.56(s,1H),7.34(t,1H),6.87-6.82(m,1H),6.73-6.65(m,2H),3.89(s,3H),3.83(s,3H)

[0317] c) Preparation of methyl 3-chloro-5-(3-methoxyphenoxy)pyridazine-4-carboxylate [ka] In a vial, methyl 3-hydroxy-5-(3-methoxyphenoxy)pyridazine-4-carboxylate (20 mg, 0.072 mmol) and phosphorus oxychloride (0.27 mL) were stirred at 75° C. for 2 hours. The reaction was monitored by LCMS. After completion, the reaction mixture was then cooled to room temperature. It is then diluted with ethyl acetate. The mixture was slowly poured into cold water (20 mL) and stirred for 5 minutes. The organic layer was separated and washed again with water (20 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The crude mixture was used directly in the next step without purification. LCMS (Method A): Retention time 0.91 min, m / z 295 (M+H)

[0318] d) Preparation of methyl 5-(3-methoxyphenoxy)-3-methyl-pyridazine-4-carboxylate [ka] Under argon, a microwave vial was charged with a solution of methyl 3-chloro-5-(3-methoxyphenoxy)pyridazine-4-carboxylate (155 mg, 0.53 mmol) in 2-methyltetrahydrofuran (3.2 mL). To this was added potassium carbonate (0.145 g, 1.05 mmol) and Pd(dppf)Cl2.CH2Cl2 (44 mg, 0.053 mmol), followed by trimethylboroxine (79 mg, 0.08 mmol). The reaction mixture was purged with argon for 5 minutes. The vial was stirred and heated at 95° C. for 16 hours. The reaction mixture was cooled to room temperature and diluted with water and ethyl acetate. The aqueous layer was extracted twice with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give a crude residue which was purified by silica gel chromatography to give methyl 5-(3-methoxyphenoxy)-3-methyl-pyridazine-4-carboxylate (100 mg, 0.365 mmol). 1 H NMR(400MHz,CDCl3)δ ppm 8.74(s,1H)7.35(t,1H)6.85(dd,1H)6.72-6.63(m,2H)3.97(s,3H)3.82(s,3H)2.76(s,3H)

[0319] e) Preparation of lithium 5-(3-methoxyphenoxy)-3-methyl-pyridazine-4-carboxylate [ka] In a vial, methyl 5-(3-methoxyphenoxy)-3-methyl-pyridazine-4-carboxylate (91 mg, 0.33 mmol) was placed in tetrahydrofuran (1.7 mL) and water (0.33 mL). Lithium hydroxide (14 mg, 0.33 mmol) was then added. The vial was sealed and stirred at room temperature for 17 hours. The progress of the reaction was monitored by LCMS. The reaction was not complete so an additional amount of lithium hydroxide (7 mg, 0.17 mmol) was added and stirred at room temperature for an additional 5 hours. Upon completion, the crude reaction mixture was concentrated under reduced pressure at 50° C. to give lithium 5-(3-methoxyphenoxy)-3-methyl-pyridazine-4-carboxylate (97 mg, 0.33 mmol), which was used directly in the next step without further purification. LCMS (Method A): Retention time 0.38 min, m / z 258(MH)

[0320] f) Preparation of N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]-5-(3-methoxyphenoxy)-3-methyl-pyridazine-4-carboxamide [ka] A drop of N,N-dimethylformamide followed by oxalyl chloride (0.073 g, 0.56 mmol) was added to a light brown suspension of lithium 5-(3-methoxyphenoxy)-3-methyl-pyridazine-4-carboxylate (0.097 g, 0.33 mmol) in 2-methyltetrahydrofuran (4.6 mL) under argon. The reaction mixture was stirred at room temperature for 1 h. The reaction progress was monitored by LCMS. After completion, the reaction mixture was concentrated under reduced pressure at 60° C. to give a dark brown oil, which was dissolved in acetonitrile (5 mL). To this was added potassium iodide (14 mg, 0.083 mmol) followed by 2-(2,4-dichlorophenyl)-2-fluoroethan-1-amine (82 mg, 0.40 mmol) under argon. The resulting dark brown solution was stirred at 75° C. for 30 min. The reaction progress was monitored by LCMS. Upon completion, the reaction mixture was diluted with ethyl acetate and the organic layer was washed with saturated aqueous sodium bicarbonate and sodium thiosulfate. The organic layers were combined, washed once more with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure at 60° C. The crude residue was purified by silica gel chromatography (cyclohexane / ethyl acetate) to give N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]-5-(3-methoxyphenoxy)-3-methyl-pyridazine-4-carboxamide (48 mg, 0.10 mmol). 1 H NMR(400MHz,CDCl3)δ ppm 8.68(s,1H)7.48-7.32(m,3H)7.19(dd,1H) 6.89(dt,1H)6.77-6.56(m,3H)6.09-5.86(m,1H)4.22-4.07(m,1H)3.84(s,3H),3.94-3.75(m,1H)2.73(s,3H) LCMS (Method A): Retention time 1.00 min, m / z 450 (M+H)

[0321] Example 16: This example illustrates the preparation of N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]-3-methyl-5-phenoxy-pyridazine-4-carboxamide (compound 2.14 of Table T2). [ka] a) Preparation of 4-bromo-5-phenoxy-pyridazin-3-ol [ka] In a vial, 4,5-dibromopyridazin-3(2H)-one (0.40 g, 1.50 mmol), cesium carbonate (1.23 g, 3.74 mmol) and phenol (0.155 g, 1.65 mmol) were stirred in dry dimethylsulfoxide (4 mL) under argon for 5 min. To this was added copper(I) iodide (14.4 mg, 0.075 mmol) and N,N-dimethylglycine (24 mg, 0.225 mmol). The resulting brown mixture was stirred at 110° C. under argon for 3 h. The mixture was diluted with ethyl acetate and water. The desired material was extracted with ethyl acetate (2×15 mL). The organic layer was washed with water, brine, dried over sodium sulfate, filtered and evaporated. The crude residue obtained was purified by silica gel chromatography (cyclohexane / ethyl acetate) to give 4-bromo-5-phenoxy-pyridazin-3-ol (240 mg, 0.9 mmol) as a white solid. LCMS (Method A): Retention time 0.74 min, m / z 267(M+H)

[0322] b) Preparation of methyl 3-hydroxy-5-phenoxy-pyridazine-4-carboxylate [ka] A glass autoclave was charged under argon with 4-bromo-5-phenoxy-pyridazin-3-ol (240 mg, 0.90 mmol), triethylamine (0.137 g, 1.35 mmol), [Pd(BINAP)(allyl)Cl] (36 mg, 0.045 mmol) and degassed methanol (9 mL). The autoclave was purged with carbon monoxide and charged to 5 bar. The reaction mixture was stirred at 80° C. for 18 h. The reaction progress was monitored by LCMS. After completion, the reaction mixture was concentrated to dryness and directly purified by silica gel chromatography (cyclohexane / ethyl acetate) to give methyl 3-hydroxy-5-(3-methoxyphenoxy)pyridazine-4-carboxylate (92 mg, 0.37 mmol). 1 H NMR(400MHz,CDCl3)δ ppm 10.77(br s,1H), 7.54(s,1H),7.48-7.42(m,2H),7.35-7.28(m,1H),7.17-7.10(m,2H),3.86(s,3H)

[0323] c) Preparation of methyl 3-chloro-5-phenoxy-pyridazine-4-carboxylate [ka] In a vial, methyl 3-hydroxy-5-(3-methoxyphenoxy)pyridazine-4-carboxylate (92 mg, 0.37 mmol) and phosphorus oxychloride (1.4 mL) were stirred at 75° C. for 2 hours. The reaction was monitored by LCMS. After completion, the reaction mixture was then cooled to room temperature. It is then diluted with ethyl acetate. The mixture was slowly poured into cold water (20 mL) and stirred for 5 minutes. The organic layer was separated and washed again with water (20 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The crude mixture was used directly in the next step without purification. LCMS (Method A): Retention time 0.89 min, m / z 265 (M+H)

[0324] d) Preparation of methyl 3-methyl-5-phenoxy-pyridazine-4-carboxylate [ka] Under argon, a microwave vial was charged with a solution of methyl 3-chloro-5-phenoxy-pyridazine-4-carboxylate (81 mg, 0.306 mmol) in 2-methyltetrahydrofuran (1.84 mL). To this was added potassium carbonate (0.085 g, 0.61 mmol) and Pd(dppf)Cl2.CH2Cl2 (25.5 mg, 0.031 mmol), followed by trimethylboroxine (46 mg, 0.367 mmol). The reaction mixture was purged with argon for 5 minutes. The vial was stirred and heated at 95° C. for 16 hours. The reaction mixture was cooled to room temperature and diluted with water and ethyl acetate. The aqueous layer was extracted twice with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give a crude residue which was purified by silica gel chromatography to give methyl 3-methyl-5-phenoxy-pyridazine-4-carboxylate (53 mg, 0.217 mmol). 1 H NMR(400MHz,CDCl3)δ ppm 8.71(s,1H)7.47(br s,2H)7.36-7.28(m,1H)7.12(d,2H)3.96(s,3H)2.77(s,3H)

[0325] e) Preparation of lithium 3-methyl-5-phenoxy-pyridazine-4-carboxylate [ka] In a vial, methyl 5-(3-methoxyphenoxy)-3-methyl-pyridazine-4-carboxylate (53 mg, 0.217 mmol) was placed in tetrahydrofuran (1.1 mL) and water (0.217 mL). Lithium hydroxide (9.2 mg, 0.217 mmol) was then added. The vial was sealed and stirred at room temperature for 18 hours. The progress of the reaction was monitored by LCMS. The reaction was not complete so an additional amount of lithium hydroxide (4.6 mg, 0.11 mmol) was added and stirred at room temperature for an additional 3 hours. Upon completion, the crude reaction mixture was concentrated under reduced pressure at 50° C. to give lithium 3-methyl-5-phenoxy-pyridazine-4-carboxylate (63 mg, 0.216 mmol), which was used directly in the next step without further purification. LCMS (Method A): Retention time 0.24 min, m / z 228(MH)

[0326] f) Preparation of N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]-3-methyl-5-phenoxy-pyridazine-4-carboxamide [ka] A drop of N,N-dimethylformamide was added followed by oxalyl chloride (0.048 g, 0.37 mmol) to a light brown suspension of lithium 3-methyl-5-phenoxy-pyridazine-4-carboxylate (0.063 g, 0.22 mmol) in 2-methyltetrahydrofuran (3 mL) under argon. The reaction mixture was stirred at room temperature for 2 hours. The reaction progress was monitored by LCMS. After completion, the reaction mixture was concentrated under reduced pressure at 60° C. to give a dark brown oil, which was dissolved in acetonitrile (4 mL). To this was added potassium iodide (11 mg, 0.067 mmol) followed by 2-(2,4-dichlorophenyl)-2-fluoroethan-1-amine (67 mg, 0.32 mmol) under argon. The resulting dark brown solution was stirred at 75° C. for 16 hours. The reaction progress was monitored by LCMS. Upon completion, the reaction mixture was diluted with ethyl acetate and the organic layer was washed with saturated aqueous sodium bicarbonate and sodium thiosulfate. The organic layers were combined, washed once more with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure at 60° C. The crude residue was purified by silica gel chromatography (cyclohexane / ethyl acetate) to give N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]-3-methyl-5-phenoxy-pyridazine-4-carboxamide (48 mg, 0.057 mmol). 1 H NMR(400MHz,CDCl3)δ ppm 8.69-8.64(m,1H)7.54-7.47(m,2H)7.44-7.33(m,3H)7.20-7.10(m,3H)6. 74-6.53(m,1H)6.06-5.87(m,1H)4.13(m,1H)3.96-3.79(m,1H)2.76(s,3H) LCMS (Method A): Retention time 0.87 min, m / z 420 (M+H)

[0327] Example 17: This example illustrates the preparation of 5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]-3-hydroxy-pyridazine-4-carboxamide (compound 2.15 of Table T2). [ka] In Example 3, methyl 4-(3-cyclopropylphenoxy)-6-oxo-1H-pyridazine-5-carboxylate is used. a) Preparation of 5-(3-cyclopropylphenoxy)-3-hydroxy-pyridazine-4-carboxylic acid [ka] Barium hydroxide octahydrate (900 mg, 5.0 mmol) was added to a stirred solution of methyl 5-(3-cyclopropylphenoxy)-3-hydroxy-pyridazine-4-carboxylate (500 mg, 2.0 mmol) in a 3:1 mixture of tetrahydrofuran / water (20 mL). The mixture was stirred at room temperature for 18 hours. The progress of the reaction was monitored by TLC and LCMS. The reaction mixture was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 5-(3-cyclopropylphenoxy)-3-hydroxy-pyridazine-4-carboxylic acid (450 mg, 1.6 mmol). The resulting residue was pure enough for the next step. 1H NMR (400MHz, dimethylsulfoxide-d6) δ ppm 13.60-13.90 (br, 1H) 13.46 (s, 1H) 7.63 (s, 1H) 7.32 (t, 1H) 7.00 (d, 1H) 6.89-6.95 (m, 2H) 1.91-2.02 (m, 1H) 0.89-1.04 (m, 2H) 0.68-0.74 (m, 2H) LCMS (Method B-QDA): Retention time 0.96 min, m / z 273(M+H)

[0328] b) 5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]-3-hydroxy-pyridazine-4-carboxamide [ka] Diisopropylethylamine (0.38 mL, 2.18 mmol) and HATU (376 mg, 0.95 mmol) were added to a mixture of 5-(3-cyclopropylphenoxy)-3-hydroxy-pyridazine-4-carboxylic acid (250 mg, 0.87 mmol) and 2-(2,4-dichlorophenyl)-2-fluoro-ethanamine (219 mg, 1.05 mmol) in dimethylformamide (2.6 mL) and stirred at room temperature for 16 h. The progress of the reaction was monitored by LCMS and TLC. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with a saturated solution of sodium bicarbonate and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to give the crude product. The crude material was purified by silica gel chromatography (cyclohexane / ethyl acetate) to give 5-(3-cyclopropylphenoxy)-N-[2-(2,4-dichlorophenyl)-2-fluoro-ethyl]-3-hydroxy-pyridazine-4-carboxamide (190 mg, 0.29 mmol). 1 H NMR(400MHz,CDCl3)δ ppm 10.64(s,1H)9.27(br s,1H)7.57(s,1H)7.50(d,1H)7.37-7.42(m,1H)7.32-7.28(m,2H)7.01(d,1H)6.89(dd,1H)6.82(t,1H)6. 03-5.92(dd,1H)4.11-4.01(m,1H)3.76-3.64(m,1H)1.94-1.87(m,1H)1.06-0.97(m,2H)0.74-0.68(m,2H) LCMS (Method B-SQD): Retention time 1.15 min, m / z 462 (M+H)

[0329] [Table 6]

[0330] [Table 7-1] [Table 7-2] [Table 7-3] [Table 7-4]

[0331] Biological Examples / Test Methods: Alternaria solani (tomato late blight) Tomato leaf discs are placed on water agar in multi-well plates (24-well format) and sprayed with the test solution. After drying, the leaf discs are inoculated with a fungal spore suspension. After appropriate incubation, the activity of the compounds is evaluated 4 dpi (days post inoculation) as preventive fungicidal activity.

[0332] The following compounds in Table T1 provided at least 80% control of Alternaria solani at 200 ppm when compared to untreated controls under the same conditions that showed extensive disease development: (Table T1, Compound): 1.2

[0333] Botryotinia fuckeliana and Botrytis cinerea (gray mold) Fungal conidia from cryogenic storage were mixed directly into nutrient broth (PDB potato dextrose broth). A DMSO solution of the test compound was placed in a microtiter plate (96-well format) and the nutrient broth containing the fungal spores was added to it. The test plate was incubated at 24°C and the inhibition of growth was determined photometrically after 72 hours.

[0334] The following compounds in Table T1 provided at least 80% control of Botryotinia fuckeliana at 20 ppm when compared to untreated controls under the same conditions that exhibited extensive disease development: (Table T1, Compound): 1.1 (Table T2, compounds): 2.1, 2.3, 2.4, 2.5, 2.6, 2.8, 2.9, 2.10, 2.11, 2.12, 2.15, 2.16

[0335] Glomerella lagenarium and Colletotrichum lagenarium (anthracnose) Fungal conidia from cryogenic storage were mixed directly into nutrient broth (PDB potato dextrose broth). A DMSO solution of the test compound was placed in a microtiter plate (96-well format) and the nutrient broth containing the fungal spores was added to it. The test plate was incubated at 24°C and the inhibition of growth was determined photometrically after 72 hours at 620 nm.

[0336] The following compounds in Table T1 provided at least 80% control of Glomerella lagenarium at 20 ppm when compared to untreated controls under the same conditions that exhibited extensive disease development: (Table T1, compounds): 1.1, 1.2 (Table T2, compounds): 2.1, 2.4, 2.5, 2.6, 2.7, 2.8, 2.9, 2.10, 2.10, 2.12, 2.15, 2.16

[0337] Blumeria graminis (syn Erysiphe graminis) (wheat powdery mildew) Wheat leaf discs are placed on agar in multiwell plates (24-well format) and sprayed with the test solution. After drying, the leaf discs are inoculated with a fungal spore suspension. After appropriate incubation, the activity of the compounds is evaluated 6-8 dpi (days post inoculation) as preventive fungicidal activity.

[0338] The following compounds provided at least 80% control of Blumeria graminis at 200 ppm when compared to untreated controls under the same conditions, which exhibited widespread disease development: (Table T1, compounds): 1.1, 1.2 (Table T2, Compound): 2.4

[0339] Monographella nivalis, Microdochium nivale, Fusarium nivale (snow rot, foot rot): Fungal conidia from cryogenic storage were mixed directly into nutrient broth (PDB potato dextrose broth). A DMSO solution of the test compound was placed in a microtiter plate (96-well format) and the nutrient broth containing the fungal spores was added to it. The test plate was incubated at 24°C and the inhibition of growth was determined photometrically after 72 hours at 620 nm.

[0340] The following compounds in Table T1 gave at least 80% control of Monographella nivalis at 20 ppm when compared to untreated controls under the same conditions, which exhibited widespread disease development: (Table T1, Compound): 1.2

[0341] Mycosphaerella arachidis, Cercospora arachidicola (early leaf spot of peanut): Fungal conidia from cryogenic storage are mixed directly into nutrient broth (PDB potato dextrose broth). A (DMSO) solution of the test compound is placed in a microtiter plate (96-well format) followed by the addition of the nutrient broth containing the fungal spores. The test plate is incubated at 24 °C and the inhibition of growth is determined photometrically 4-5 days after application.

[0342] The following compounds from Table T1 provided at least 80% control of Mycosphaerella arachidis at 20 ppm when compared to untreated controls that showed extensive disease development under the same conditions: (Table T2, compounds): 2.7, 2.13, 2.16

[0343] Pyrenophora teres (net blotch of barley) Barley leaf discs are placed on agar in multi-well plates (24-well format) and sprayed with the test solution. After drying, the leaf discs are inoculated with a fungal spore suspension. After appropriate incubation, the activity of the compounds is evaluated 4 dpi (days post inoculation) as preventive fungicidal activity.

[0344] The following compounds in Table T1 gave at least 80% control of Pyrenophora teres at 200 ppm when compared to untreated controls under the same conditions which showed extensive disease development: (Table T1, Compound): 1.2

[0345] Sclerotinia sclerotiorum (sclerotinia rot, white mold) Fungal mycelial fragments prepared from fresh liquid cultures were mixed directly into nutrient broth (PDB potato dextrose broth). DMSO solutions of test compounds were placed in microtiter plates (96-well format) and nutrient broth containing fungal spores was added to it. Test plates were incubated at 24°C and inhibition of growth was determined photometrically after 72 hours at 620 nm.

[0346] The following compounds in Table T1 gave at least 80% control of Sclerotinia sclerotiorum at 20 ppm when compared to untreated controls under the same conditions which showed extensive disease development: (Table T1, Compound): 1.2

Claims

1. Formula (I) 【Chemistry 1】 (In the formula, R 1 is C 1 ~C 4 -Alkyl, C 1 ~C 2 -haloalkyl, C 1 ~C 4 -alkoxy, C 1 ~C 4 - alkylsulfanyl, C 1 ~C 4 -Alkylsulfinyl, C 1 ~C 4 - alkylsulfonyl, C 1 ~C 2 -haloalkoxy, C 2 ~C 3 -alkenyl, C 2 ~C 3 -haloalkenyl, C 2 ~C 3 -alkynyl, C 3 ~C 6 -cycloalkyl, C 3 ~C 6 -cycloalkyloxy, C 2 ~C 3 -alkenyloxy and C 2 ~C 3 -phenyl substituted with a single substituent selected from -alkynyloxy; or R 1 is phenyl optionally substituted with 1, 2 or 3 substituents, which may be the same or different, independently selected from hydroxyl, halogen, mercapto, amino, cyano, methyl, ethyl, propyl, isopropyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, propyloxy, isopropyloxy, tert-butoxy, allyloxy, propargyloxy, methylsulfanyl, methylsulfonyl, difluoromethoxy, trifluoromethoxy, cyclopropyl, cyclobutyl and cyclopropyloxy; or R 1 is a 6-membered monocyclic heteroaryl ring containing 1, 2 or 3 nitrogen atoms, said heteroaryl ring being selected from the group consisting of hydroxyl, halogen, mercapto, amino, cyano, C 1 ~C 4 -Alkyl, C 1 ~C 2 -haloalkyl, C 1 ~C 4 - alkylsulfanyl, C 1 ~C 4 -Alkylsulfinyl, C 1 ~C 4 - alkylsulfonyl, C 2 ~C 3 -alkenyl, C 2 ~C 3 -haloalkenyl, C 2 ~C 3 -alkynyl, C 3 ~C 6 -cycloalkyl, C 1 ~C 4 -alkoxy, C 1 ~C 2 -haloalkoxy, C 2 ~C 3 -alkenyloxy, C 2 ~C 3 -alkynyloxy and C 3 ~C 6 -optionally substituted with 1 or 2 substituents, which may be the same or different, independently selected from cycloalkyloxy; R 2 and R 3 is hydrogen, halogen, cyano, hydroxy, C 1 ~C 3 -Alkyl, C 1 ~C 3 -alkoxy and C 1 ~C 2 -haloalkoxy; R 4 is C 1 ~C 4 -Alkyl, C 1 ~C 2 -haloalkyl, C 1 ~C 4 -alkoxy, C 1 ~C 4 - alkylsulfanyl, C 1 ~C 4 -Alkylsulfinyl, C 1 ~C 4 - alkylsulfonyl, C 1 ~C 2 -haloalkoxy, C 2 ~C 3 -alkenyl, C 2 ~C 3 -haloalkenyl, C 2 ~C 3 -alkynyl, C 3 ~C 6 -cycloalkyl and C 3 ~C 6 -phenyl substituted with a single substituent selected from -cycloalkyloxy; or R 4 is phenyl optionally substituted with 1, 2 or 3 substituents, which may be the same or different, independently selected from hydroxyl, halogen, mercapto, amino, cyano, methyl, ethyl, propyl, isopropyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, propyloxy, isopropyloxy, tert-butoxy, allyloxy, propargyloxy, methylsulfanyl, methylsulfonyl, difluoromethoxy, trifluoromethoxy, cyclopropyl, cyclobutyl and cyclopropyloxy; or R 4 is a 6-membered monocyclic heteroaryl ring containing 1, 2 or 3 nitrogen atoms, said heteroaryl ring being selected from the group consisting of hydroxyl, halogen, mercapto, amino, cyano, C 1 ~C 4 -Alkyl, C 1 ~C 2 -haloalkyl, C 1 ~C 4 -alkoxy, C 2 ~C 3 -alkenyloxy, C 2 ~C 3 -alkynyloxy, C 1 ~C 4 - alkylsulfanyl, C 1 ~C 4 -Alkylsulfinyl, C 1 ~C 4 - alkylsulfonyl, C 1 ~C 2 -haloalkyloxy, C 3 ~C 6 -cycloalkyl and C 3 ~C 6 -optionally substituted with 1 or 2 substituents, which may be the same or different, independently selected from cycloalkyloxy; A is (A-2), (A-1), or (A-3): 【Chemistry 2】 wherein the jagged line defines the point of attachment to the remainder of the compound of formula (I). Selected from: R 5 is hydrogen, halogen, cyano, C 1 ~C 3 -Alkyl and C 1 ~C 3 - selected from alkoxy; R 6 is hydrogen, hydroxy, cyano, halogen, C 1 ~C 3 -Alkyl, C 2 ~C 3 -alkenyl, C 2 ~C 3 -alkynyl, C 1 ~C 3 -alkoxy, C 1 ~C 3 -fluoroalkyl, C 1 ~C 3 -fluoroalkoxy and C 3 ~C 4 -cycloalkyl; R 7 is hydrogen, halogen, cyano, C 1 ~C 3 -Alkyl and C 1 ~C 3 - selected from alkoxy; R 8 is hydrogen, hydroxy, cyano, mercaptyl, halogen, C 1 ~C 3 -Alkyl, C 2 ~C 3 -alkenyl, C 2 ~C 3 -alkynyl, C 1 ~C 3 -alkoxy, C 1 ~C 3 -fluoroalkyl, C 1 ~C 3 -fluoroalkoxy and C 3 ~C 4 -cycloalkyl; or R 9 is hydrogen, hydroxy, halogen, cyano and C 1 ~C 3 -alkyl) or the agrochemically acceptable salts, stereoisomers, enantiomers and N-oxides of the compounds of formula I above.

2. The compound of claim 1, wherein A is A-2.

3. R 7 3. The compound of claim 2, wherein is selected from hydrogen, fluoro, chloro, cyano, methyl, ethyl, methoxy and ethoxy.

4. R 8 is selected from hydrogen, hydroxy, cyano, mercaptyl, fluoro, chloro, methyl and ethyl, or R 8 The compound of claim 2, wherein is hydrogen, hydroxy, chloro, methyl, ethyl, isopropyl, methoxy, cyclopropyl, isoprenyl, 2-cyclopropylethynyl, 2-methylallyloxy, or isopropoxy.

5. R 7 is hydrogen, and R 8 The compound of claim 2, wherein is selected from hydrogen, hydroxy, chloro, methyl, ethyl, isopropyl, methoxy, isopropoxy, cyclopropyl, isoprenyl, 2-cyclopropylethynyl, 2-methylallyloxy.

6. A is A-1 and R 5 is selected from hydrogen, fluoro, chloro, cyano, methyl, ethyl, methoxy, and ethoxy; R 6 2. The compound of claim 1, wherein is selected from hydrogen, hydroxy, cyano, fluoro, chloro, methyl, or ethyl.

7. A is A-3 and R 9 2. The compound of claim 1, wherein is selected from hydrogen, hydroxy, chloro, cyano, methyl, and ethyl.

8. R 1 is phenyl, pyridine, pyrazine, pyrimidine or pyridazine, wherein said phenyl, pyridine, pyrazine, pyrimidine or pyridazine is optionally substituted with one or two substituents independently selected from hydroxyl, halogen, mercapto, amino, cyano, methyl, ethyl, propyl, isopropyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, propoxy, isopropoxy, tert-butoxy, allyloxy, propargyloxy, methylsulfanyl, methylsulfonyl, difluoromethoxy, trifluoromethoxy, cyclopropyl, cyclobutyl and cyclopropyloxy.

9. R 1 Examples of the fluorophenyl include 2-fluoro-3-cyclopropylphenyl, 2-fluoro-3-methylphenyl, 2-fluorophenyl, 3-(difluoromethoxy)phenyl, 3-(trifluoromethoxy)phenyl, 2-(trifluoromethyl)pyridin-4-yl, 3-ethoxyphenyl, 3-ethylphenyl, 3-ethynylphenyl, 3-fluorophenyl, 4-(difluoromethoxy)phenyl, 4-(trifluoromethoxy)phenyl, 4-chlorophenyl, 4-cyanophenyl, 4-ethoxyphenyl, 4-ethylphenyl, 4-fluorophenyl, 3-methoxyphenyl, 3,4-dichlorophenyl, 3,4-difluorophenyl, 3,4-dimethoxyphenyl, 3,5-dichlorophenyl, 3,5-difluorophenyl, 3-cyanophenyl, 2-methylpyrimidin-4-yl, 2-(trifluoromethyl)pyridin-4-yl, 3-(trifluoromethyl)pyridin-2-yl, 3-methoxypyridin phenylpyridin-2-yl, 3-methylpyridin-2-yl, 2-chloropyridin-3-yl, 2-chloropyridin-4-yl, 2-cyanopyridin-3-yl, 2-fluoropyridin-3-yl, 2-methoxypyridin-4-yl, 2-methylpyridin-3-yl, 5-(trifluoromethyl)pyridin-3-yl, 5-chloropyridin-3-yl, 5-cyanopyridin-3-yl, 5-cyclopropylpyridin-3-yl, 5-methylpyridin-3-yl, The compound of claim 1, which is 5-pyridazin-4-yl, 6-(trifluoromethyl)pyridin-3-yl, 6-chloropyridin-2-yl, 6-cyanopyridin-3-yl, 6-cyclopropylpyridin-2-yl, 6-methoxypyridin-3-yl, 6-methyl-2-pyridyl, 6-methylpyridazin-3-yl, 6-methylpyridin-2-yl, 6-methylpyridin-3-yl, pyridin-3-yl, pyridin-4-yl, or phenyl.

10. R 1 The compound of claim 1, wherein is phenyl, 3-trifluoromethylphenyl, 3-methoxyphenyl, 3-cyclopropylphenyl, 3-cyclopropyl-2-fluorophenyl, or 6-chloropyridin-3-yl.

11. R 1 The compound of claim 1, wherein is phenyl, 3-methoxyphenyl, or 3-cyclopropylphenyl.

12. R 2 and R 3 2. The compound of claim 1, wherein is independently selected from hydrogen, fluoro, methyl, ethyl, cyano, hydroxy, methoxy, ethoxy, methoxymethyl, and difluoromethoxy.

13. R 4 is phenyl, pyridine, pyrazine, pyrimidine or pyridazine, wherein said phenyl, pyridine, pyrazine, pyrimidine or pyridazine is optionally substituted with one or two substituents independently selected from hydroxyl, halogen, mercapto, amino, cyano, methyl, ethyl, propyl, isopropyl, difluoromethyl, trifluoromethyl, methoxy, ethoxy, propyloxy, isopropyloxy, tert-butoxy, allyloxy, propargyloxy, methylsulfanyl, methylsulfonyl, difluoromethoxy, trifluoromethoxy, cyclopropyl, cyclobutyl and cyclopropyloxy.

14. R 4 is 2,4-dichlorophenyl, 3-methylphenyl, 4-methylphenyl, 2,4-dimethylphenyl, 3,4-dimethylphenyl, 2-chloro-4-cyanophenyl, 2-methyl-4-cyanophenyl, 2,4-difluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3-fluorophenyl, 2-cyanophenyl, 3-cyanophenyl, 4-cyanophenyl, 3-methoxyphenyl, 4-methoxyphenyl, 3,4-dimethoxyphenyl, phenyl, 6-chloro-3-pyridyl, 6-cyano-3-pyridyl, or 6-methyl-3-pyridyl.

15. R 4 The compound of claim 1, wherein is 2,4-dichlorophenyl, 2,4-dimethylphenyl, or 6-chloro-3-pyridyl.

16. 16. An agrochemical composition comprising a fungicidally effective amount of a compound according to any one of claims 1 to 15.

17. 17. The composition of claim 16, further comprising at least one additional active ingredient and / or an agrochemically acceptable diluent or carrier.

18. A method for controlling or preventing infestation of useful plants by phytopathogenic microorganisms, comprising applying a fungicidally effective amount of a compound according to any one of claims 1 to 15 to said plants, parts thereof or their habitats.

19. Use of a compound according to any one of claims 1 to 15 as a bactericide or fungicide.

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