Microbicide tetrahydroisoquinoline derivatives

Abstract

Compounds of formula (I) wherein the substituents are as defined in claim 1, and agrochemically acceptable salts, stereoisomers, enantiomers, tautomers and N-oxides of these compounds, which may be used as fungicides. JPEG2025538674000097.jpg58161

Description

[Technical Field]

[0001] The present invention relates to microbicidal tetrahydroisoquinoline derivatives as active ingredients having, for example, microbicidal, particularly fungicidal, activity. The present invention also relates to the preparation of these tetrahydroisoquinoline derivatives, intermediates useful in the preparation of these tetrahydroisoquinoline derivatives, the preparation of these intermediates, agrochemical compositions comprising at least one of the tetrahydroisoquinoline derivatives, the preparation of these compositions, and the use of the tetrahydroisoquinoline derivatives or compositions in agriculture or horticulture to control or prevent infestation of plants, harvested food crops, seeds, or non-living materials by phytopathogenic microorganisms, particularly fungi. DETAILED DESCRIPTION OF THE INVENTION

[0002] According to a first aspect of the present invention, a compound of formula (I) [ka] (In the formula, R 1 is selected from hydrogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, or C3-C6-cycloalkyl, R 2 is selected from hydrogen, halogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C1-C4-alkylcarbonyl, N—C1-C4-alkoxy-C—C1-C4-alkyl-carbonimidoyl, N-hydroxy-C—C1-C4-alkyl-carbonimidoyl or C1-C4-alkoxycarbonyl, R 3 is selected from hydrogen, halogen, C1-C4-haloalkyl, or C1-C4-alkyl, R 4 is selected from hydrogen, halogen, C1-C4-haloalkyl, C3-C6-cycloalkyl, or C1-C4-alkyl, R 5 and R 6are independently selected from hydrogen or C1-C4-alkyl, R 7 is selected from hydrogen, C1-C4-alkyl, C1-C4-alkylcarbonyl, N-C1-C4 alkoxy-C-C1-C4 alkyl-carbonimidoyl, N-hydroxy-C-C1-C4-alkyl-carbonimidoyl, C1-C4-alkoxycarbonyl, N-methoxy-N-methyl-carbonyl, C1-C4-alkylaminocarbonyl, di(C1-C4 alkylamino)carbonyl, phenyl, 5- to 6-membered heteroaryl, or C3-C6-cycloalkyl; said 5- to 6-membered heteroaryl may have 1, 2, 3, or 4 identical or unsubstituted aryls selected from N, O, or S. contain different heteroatoms, with the proviso that only one is O or S; said phenyl and 5- to 6-membered heteroaryl are unsubstituted or substituted with 1, 2 or 3 identical or different substituents selected from the group consisting of halogen, C1-C4-haloalkyl, cyano, carboxy, C1-C4-alkyl and C1-C4-alkoxy; said C3-C6-cycloalkyl are unsubstituted or substituted with 1, 2 or 3 identical or different substituents selected from the group consisting of halogen, C1-C4-haloalkyl, cyano, C1-C4-alkyl or C1-C4-alkoxy; B 1 is CR 10 or N; B 2 is CR 11 or N; R 8 , R 9 , R 10 and R 11is hydrogen, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C4-alkenyloxy, C2-C4-alkynyloxy, C1-C4-alkylsulfanyl, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-alkoxy-C1-C4-alkyl, N-C1-C4-alkylamino, N,N-di(C1-C4-alkyl)amino, C1-C4-alkoxycarbonyl, C1-C4-alkylcarbonyl, N-C1-C4-alkoxy-C1-C4-alkyl-carbonimidoyl, N-hydroxy-C1-C4-alkyl-carbonimidoyl, hydroxy wherein the 5- to 6-membered heteroaryl contains 1, 2, 3 or 4 identical or different heteroatoms selected from N, O or S, provided that only one is O or S; wherein any of the phenyl, 5- to 6-membered heteroaryl and C3-C6-cycloalkyl is unsubstituted or substituted with 1, 2, 3 or up to the maximum possible number of identical or different substituents selected from the group consisting of halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl and C1-C4-alkoxy; W is O, N, S, *-CH2O- # , "-CH2NH- # , "-CH2S- # or a bond, where the star (*) indicates the position of the link to the carbonyl group, and # indicates Z 1 indicates the position where it is connected to; Z 1is selected from C1-C6 alkyl, phenyl, or 6-membered heteroaryl; wherein said C1-C6-alkyl is unsubstituted or is selected from halogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C4-alkenyloxy, C2-C4-alkynyloxy, C1-C4-alkylsulfanyl, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-alkoxy-C1-C4-alkenyloxy, substituted by one, two or three identical or different substituents selected from alkyl, C1-C4-alkoxycarbonyl, C1-C4-alkylcarbonyl, N-C1-C4-alkoxy-C-C1-C4-alkyl-carbonimidoyl, N-hydroxy-C-C1-C4-alkyl-carbonimidoyl, hydroxy, trifluoromethylsulfonyloxy, cyano, carboxy, phenyl, a 5- to 6-membered saturated or partially saturated heterocycle, a 5- to 6-membered heteroaryl or a C3-C6-cycloalkyl; any of the 5- to 6-membered heteroaryls contains 1, 2, or 3 identical or different heteroatoms selected from N, O, or S, provided that only one is O or S; any of the 5- to 6-membered saturated or partially saturated heterocycles contains 1, 2, or 3 identical or different heteroatoms selected from N, O, or S, provided that only one is O or S; any of the phenyls, any of the 6-membered heteroaryls, any of the 5- to 6-membered heteroaryls, and any of the 5- to 6-membered saturated or partially saturated heterocycles is unsubstituted or or substituted with one, two, three or up to the maximum possible number of identical or different substituents selected from the group consisting of halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl and C1-C4-alkoxy; any of said C3-C6-cycloalkyl being unsubstituted or substituted with one, two, three or up to the maximum possible number of identical or different substituents selected from the group consisting of halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl and C1-C4-alkoxy), or an agrochemically acceptable salt, stereoisomer, or N-oxide thereof, provided that the compound of formula (I) is [ka] [ka] or an agriculturally acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof.

[0003] The PubChem unique identifiers (compound identifier CIDs) given for the abandoned compounds above, PubChem Compound CIDs, refer to the compound identification numbers for each compound on the PubChem website https: / / pubchem.ncbi.nlm.nih.gov / .

[0004] Surprisingly, it has been found that the compounds of formula (I) have, for practical purposes, a very advantageous level of biological activity for protecting plants against diseases caused by fungi.

[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) according to the present invention. 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, which comprises applying to said plants, parts thereof or their habitat a fungicidally effective amount of a compound of formula (I) according to the present invention, or a composition comprising a compound of formula (I).

[0007] According to a fourth aspect of the present invention, there is provided a compound of formula (I) [ka] (In the formula, R 1is selected from hydrogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, or C3-C6-cycloalkyl, R 2 is selected from hydrogen, halogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C1-C4-alkylcarbonyl, N—C1-C4-alkoxy-C—C1-C4-alkyl-carbonimidoyl, N-hydroxy-C—C1-C4-alkyl-carbonimidoyl or C1-C4-alkoxycarbonyl, R 3 is selected from hydrogen, halogen, C1-C4-haloalkyl, or C1-C4-alkyl, R 4 is selected from hydrogen, halogen, C1-C4-haloalkyl, C3-C6-cycloalkyl, or C1-C4-alkyl, R 5 and R 6 are independently selected from hydrogen or C1-C4-alkyl, R 7is selected from hydrogen, C1-C4-alkyl, C1-C4-alkylcarbonyl, N-C1-C4 alkoxy-C-C1-C4 alkyl-carbonimidoyl, N-hydroxy-C-C1-C4-alkyl-carbonimidoyl, C1-C4-alkoxycarbonyl, N-methoxy-N-methyl-carbonyl, C1-C4-alkylaminocarbonyl, di(C1-C4 alkylamino)carbonyl, phenyl, 5- to 6-membered heteroaryl, or C3-C6-cycloalkyl, wherein the 5- to 6-membered heteroaryl is selected from 1, 2, 3, or 4 identical or different groups selected from N, O, or S. wherein said phenyl and 5- to 6-membered heteroaryl are unsubstituted or substituted with 1, 2 or 3 identical or different substituents selected from the group consisting of halogen, C1-C4-haloalkyl, cyano, carboxy, C1-C4-alkyl and C1-C4-alkoxy, and said C3-C6-cycloalkyl is unsubstituted or substituted with 1, 2 or 3 identical or different substituents selected from the group consisting of halogen, C1-C4-haloalkyl, cyano, C1-C4-alkyl or C1-C4-alkoxy, B 1 is CR 10 or N; B 2 is CR 11 or N; R 8 , R 9 , R 10 and R 11is hydrogen, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C4-alkenyloxy, C2-C4-alkynyloxy, C1-C4-alkylsulfanyl, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-alkoxy-C1-C4-alkyl, N-C1-C4-alkylamino, N,N-di(C1-C4-alkyl)amino, C1-C4-alkoxycarbonyl, C1-C4-alkylcarbonyl, N-C1-C4-alkoxy-C1-C4-alkyl-carbonimidoyl, N-hydroxy-C1-C4-alkyl-carbonimidoyl, hydroxy wherein the 5- to 6-membered heteroaryl contains 1, 2, 3 or 4 identical or different heteroatoms selected from N, O or S, provided that only one is O or S; and wherein any of the phenyl, 5- to 6-membered heteroaryl and C3-C6-cycloalkyl is unsubstituted or substituted with 1, 2, 3 or up to the maximum possible number of identical or different substituents selected from the group consisting of halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl and C1-C4-alkoxy; W is O, N, S, *-CH2O- # , "-CH2NH- # , "-CH2S- # , or "-CH2- # wherein the star (*) indicates the position of attachment to the carbonyl group and # indicates Z 1 indicates the position where it is connected to Z 1is selected from C1-C6 alkyl, phenyl, or 6-membered heteroaryl, wherein the C1-C6-alkyl is unsubstituted or is selected from halogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C4-alkenyloxy, C2-C4-alkynyloxy, C1-C4-alkylsulfanyl, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-alkoxy-C1-C 4-alkyl, C1-C4-alkoxycarbonyl, C1-C4-alkylcarbonyl, N-C1-C4-alkoxy-C-C1-C4-alkyl-carbonimidoyl, N-hydroxy-C-C1-C4-alkyl-carbonimidoyl, hydroxy, trifluoromethylsulfonyloxy, cyano, carboxy, phenyl, 5- to 6-membered saturated or partially saturated heterocycle, 5- to 6-membered heteroaryl, or C3-C6-cycloalkyl, and Any of the 5- to 6-membered heteroaryls contains 1, 2, or 3 of the same or different heteroatoms selected from N, O, or S, provided that only one is O or S; any of the 5- to 6-membered saturated or partially saturated heterocyclic rings contains 1, 2, or 3 of the same or different heteroatoms selected from N, O, or S, provided that only one is O or S; any of the phenyls, any of the 5- to 6-membered heteroaryls, and any of the 5- to 6-membered saturated or partially saturated heterocyclic rings is unsubstituted or halogenated. , cyano, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, and C1-C4-alkoxy, any of which C3-C6-cycloalkyl is unsubstituted or substituted with 1, 2, 3, or up to the maximum possible number of identical or different substituents selected from the group consisting of halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, and C1-C4-alkoxy, or an agrochemically acceptable salt, stereoisomer, or N-oxide thereof, provided that the compound of formula (I) is [ka] [ka] or an agriculturally acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof.

[0008] According to another aspect of the present invention, a compound of formula (I) [ka] (In the formula, R 1 is selected from hydrogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, or C3-C6-cycloalkyl, R 2 is selected from hydrogen, halogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C1-C4-alkylcarbonyl, N—C1-C4-alkoxy-C—C1-C4-alkyl-carbonimidoyl, N-hydroxy-C—C1-C4-alkyl-carbonimidoyl or C1-C4-alkoxycarbonyl, R 3 is selected from hydrogen, halogen, C1-C4-haloalkyl, or C1-C4-alkyl, R 4 is selected from hydrogen, halogen, C1-C4-haloalkyl, C3-C6-cycloalkyl, or C1-C4-alkyl, R 5 and R 6 are independently selected from hydrogen or C1-C4-alkyl, R 7is selected from hydrogen, C1-C4-alkyl, C1-C4-alkylcarbonyl, N-C1-C4 alkoxy-C-C1-C4 alkyl-carbonimidoyl, N-hydroxy-C-C1-C4-alkyl-carbonimidoyl, C1-C4-alkoxycarbonyl, N-methoxy-N-methyl-carbonyl, C1-C4-alkylaminocarbonyl, di(C1-C4 alkylamino)carbonyl, phenyl, 5- to 6-membered heteroaryl, or C3-C6-cycloalkyl, wherein the 5- to 6-membered heteroaryl is selected from 1, 2, 3, or 4 identical or different groups selected from N, O, or S. wherein said phenyl and 5- to 6-membered heteroaryl are unsubstituted or substituted with 1, 2 or 3 identical or different substituents selected from the group consisting of halogen, C1-C4-haloalkyl, cyano, carboxy, C1-C4-alkyl and C1-C4-alkoxy, and said C3-C6-cycloalkyl is unsubstituted or substituted with 1, 2 or 3 identical or different substituents selected from the group consisting of halogen, C1-C4-haloalkyl, cyano, C1-C4-alkyl or C1-C4-alkoxy, B 1 But, CR 10 or N; B 2 But, CR 11 or N; R 8 , R 9 , R 10 and R 11is hydrogen, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C4-alkenyloxy, C2-C4-alkynyloxy, C1-C4-alkylsulfanyl, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-alkoxy-C1-C4-alkyl, N-C1-C4-alkylamino, N,N-di(C1-C4-alkyl)amino, C1-C4-alkoxycarbonyl, C1-C4-alkylcarbonyl, N-C1-C4-alkoxy-C1-C4-alkyl-carbonimidoyl, N-hydroxy-C1-C4-alkyl-carbonimidoyl, hydroxy wherein the 5- to 6-membered heteroaryl contains 1, 2, 3 or 4 identical or different heteroatoms selected from N, O or S, provided that only one is O or S; and wherein any of the phenyl, 5- to 6-membered heteroaryl and C3-C6-cycloalkyl is unsubstituted or substituted with 1, 2, 3 or up to the maximum possible number of identical or different substituents selected from the group consisting of halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl and C1-C4-alkoxy; W is O, N, S, *-CH2O- # , "-CH2NH- # , "-CH2S- # or a bond, where the star (*) indicates the position of the link to the carbonyl group, and # indicates Z 1 indicates the position where it is connected to Z 1is selected from C1-C6 alkyl, phenyl, or 6-membered heteroaryl, wherein the C1-C6-alkyl is unsubstituted or is selected from halogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C4-alkenyloxy, C2-C4-alkynyloxy, C1-C4-alkylsulfanyl, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-alkoxy-C1-C 4-alkyl, C1-C4-alkoxycarbonyl, C1-C4-alkylcarbonyl, N-C1-C4-alkoxy-C-C1-C4-alkyl-carbonimidoyl, N-hydroxy-C-C1-C4-alkyl-carbonimidoyl, hydroxy, trifluoromethylsulfonyloxy, cyano, carboxy, phenyl, 5- to 6-membered saturated or partially saturated heterocycle, 5- to 6-membered heteroaryl, or C3-C6-cycloalkyl, and Any of the 5- to 6-membered heteroaryls contains 1, 2, or 3 of the same or different heteroatoms selected from N, O, or S, provided that only one is O or S; any of the 5- to 6-membered saturated or partially saturated heterocyclic rings contains 1, 2, or 3 of the same or different heteroatoms selected from N, O, or S, provided that only one is O or S; any of the phenyls, any of the 5- to 6-membered heteroaryls, and any of the 5- to 6-membered saturated or partially saturated heterocyclic rings is unsubstituted or halogenated. , cyano, C1-C4-alkyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, and C1-C4-alkoxy, any of which C3-C6-cycloalkyl is unsubstituted or substituted with 1, 2, 3, or up to the maximum possible number of identical or different substituents selected from the group consisting of halogen, cyano, C1-C4-alkyl, C1-C4-haloalkyl, and C1-C4-alkoxy, or an agrochemically acceptable salt, stereoisomer, or N-oxide thereof, provided that the compound of formula (I) is [ka] [ka] or an agriculturally acceptable salt, stereoisomer, enantiomer, tautomer or N-oxide thereof.

[0009] According to this particular aspect of the invention, the use may not include methods involving the treatment of the human or animal body by surgery or therapy and diagnostic methods performed on the human or animal body.

[0010] The compounds of formula (I) having at least one basic center can form, for example, acid addition salts with strong inorganic acids, such as mineral acids such as perchloric acid, sulfuric acid, nitric acid, nitrous acid, phosphoric acid, or hydrohalic acids; with strong organic carboxylic acids, such as unsubstituted or halogen-substituted C1-C4 alkanecarboxylic acids, such as acetic acid; with saturated or unsaturated dicarboxylic acids, such as oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid, or phthalic acid; with hydroxycarboxylic acids, such as ascorbic acid, lactic acid, malic acid, tartaric acid, citric acid, or benzoic acid; or with organic sulfonic acids, such as unsubstituted or halogen-substituted C1-C4 alkane or arylsulfonic acids, such as methane or p-toluenesulfonic acid. Compounds of formula (I) having at least one acidic group can, for example, form salts with bases, for example mineral salts, for example alkali metal or alkaline earth metal salts, for example sodium, potassium or magnesium salts, or salts with ammonia or organic amines, for example morpholine, piperidine, pyrrolidine, mono-, di- or tri-lower alkylamines, for example ethyl, diethyl, triethyl or dimethylpropylamine, or mono-, di- or trihydroxy-lower alkylamines, for example mono-, di- or triethanolamine.

[0011] In each case, the compounds of formula (I) according to the invention are in free form, in oxidized form as N-oxides or in salt form, for example in agriculturally usable salt form.

[0012] N-oxides are the oxidized forms of tertiary amines or nitrogen-containing heteroaromatic compounds, as described, for example, in the book "Heterocyclic N-oxides" by A. Albini and S. Pietra, CRC Press, Boca Raton 1991.

[0013] The compounds of formula (I) according to the invention also include the hydrates which may be formed during salt formation.

[0014] When a substituent is designated as "optionally substituted," it means that such substituent may be substituted with one or more of the same or different substituents, for example, 1, 2, or 3 R x It means that it may or may not have a substituent. For example, C1-C6 alkyl substituted with 1, 2 or 3 halogens includes -CH2Cl, -CHCl2, -CCl 3、 Examples include, but are not limited to, -CHF, -CHF, -CF, -CHCF, or -CFCH groups. As another example, C-C alkoxy substituted with 1, 2, or 3 halogens includes, but is not limited to, CHClO-, CHClO-, CClO-, CHFO-, CHFO-, CFO-, CFCHO-, or CHCFO- groups. Furthermore, the term "optionally substituted" as used herein can be used interchangeably with the term "unsubstituted or substituted."

[0015] As used herein, the term "halogen" or "halo" refers to fluorine (fluoro), chlorine (chloro), bromine (bromo) or iodine (iodo), preferably fluorine, chlorine or bromine. This also applies correspondingly to halogen in combination with other meanings, such as haloalkyl, haloalkenyl, haloalkynyl, haloalkoxy, and halocycloalkyl.

[0016] As used herein, amino refers to the group —NH 2 .

[0017] As used herein, cyano refers to a -CN group.

[0018] As used herein, the term "hydroxyl" or "hydroxy" refers to an --OH group.

[0019] As used herein, the term "carboxylic acid" refers to a -COOH group.

[0020] As used herein, "C1-C n The term "-alkyl" refers to a saturated straight or branched hydrocarbon group having 1 to n carbon atoms bonded via any of the carbon atoms, such as any one of the following radicals: methyl, ethyl, n-propyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, n-pentyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl or 1-ethyl-2-methylpropyl.

[0021] As used herein, "C2-C nThe term "-alkenyl" refers to a straight or branched alkenyl chain moiety having 2 to n carbon atoms and one or two double bonds, for example ethenyl, prop-1-enyl, but-2-enyl.

[0022] As used herein, "C2-C n The term "-alkynyl" refers to a straight or branched alkynyl chain moiety having 2 to n carbon atoms and one triple bond, for example, ethynyl, prop-2-ynyl, but-3-ynyl.

[0023] As used herein, "C3-C n The term "-cycloalkyl" refers to a 3 to n-membered cycloalkyl radical, such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

[0024] As used herein, "C1-C n The term "C2-C alkoxy" refers to any one of the linear or branched saturated alkyl groups having 1 to n carbon atoms (as defined above) attached through an oxygen atom, i.e., for example, methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methylpropoxy, 2-methylpropoxy, and 1,1-dimethylethoxy radicals. n The term "-alkenyloxy" refers to a straight or branched alkenyl chain having 2 to n carbon atoms (as defined above) attached through an oxygen atom.

[0025] As used herein, "C2-C n The term "alkynyloxy" refers to a group of groups of the formula -OR a (R a is the general definition of C2~C n It refers to the radical of an alkynyl group.

[0026] As used herein, "C1-C n -Alkoxy-C1~C n The term "-alkyl" refers to C1-C n-refers to an alkyl radical (as defined above) substituted with an alkoxy group. Examples are methoxymethyl, methoxyethyl, ethoxymethyl and propoxymethyl.

[0027] As used herein, "C3-C n -Cycloalkyl-C1-C n The term "-alkyl" refers to C3 to C n - refers to an alkyl radical (as above) substituted with a cycloalkoxy group. Examples are cyclopropylmethyl, cyclopropylethyl. Similarly, "C3-C n -Halocycloalkyl-C1-C n "-Alkyl" refers to an alkyl radical substituted with a cycloalkyl group, where the cycloalkyl group is substituted with one or more of the same or different halogen atoms. Examples are 3,3-difluorobutylmethyl and 1-chlorocyclopropylmethyl.

[0028] As used herein, "C1-C nThe term "haloalkyl" refers to a linear or branched saturated alkyl radical having 1 to n carbon atoms, bonded via any of the carbon atoms (as defined above), in which some or all of the hydrogen atoms in these groups may be replaced by fluorine, chlorine, bromine and / or iodine, i.e., for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl, or nonafluorobutyl. Thus, the term "C1-C2 fluoroalkyl" refers to any one of C1-C2 alkyl radicals having 1, 2, 3, 4, or 5 fluorine atoms, such as difluoromethyl, trifluoromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl, or pentafluoroethyl. Similarly, as used herein, "C2-C n -haloalkenyl" or "C2-C n The term "haloalkynyl" refers to any C-C alkyl group substituted with one or more halogen atoms, which may be the same or different. n Alkenyl or C2-C nSimilarly, as used herein, "C-C" refers to an alkynyl radical. n -halocycloalkyl" or "C1-C n The term "haloalkoxy" refers to any C-C alkyl group substituted with one or more halo atoms, which may be the same or different. n -cycloalkyl radical or C1-C n -refers to alkoxy radicals.

[0029] As used herein, "C1-C n -alkylthio" or "C1-C n The term "-alkylsulfanyl" refers to a C1-C alkyl group linked through a sulfur atom. n -refers to alkyl groups.

[0030] As used herein, "C1-C n -haloalkylthio" or "C1-C n The term "haloalkylsulfanyl" refers to a C-C alkyl group linked through a sulfur atom. n Refers to haloalkyl groups.

[0031] As used herein, "C1-C n The term "-alkylsulfinyl" refers to a C1-C alkylsulfinyl group linked through the sulfur atom of the sulfinyl (or S(=O)-) group. n Refers to an alkyl group.

[0032] As used herein, "C1-C n The term "-alkylsulfonyl" refers to a C1-C2 alkyl group linked through the sulfur atom of the sulfonyl (or S(=O)2-) group. n Refers to an alkyl group.

[0033] As used herein, "C1-C n Alkylsulfonyl-C1~C n The term "alkyl" refers to C1-C n C1-C substituted with alkylsulfonyl groups n Refers to alkyl radicals.

[0034] As used herein, "C1-C n The term "alkylcarbonyl" refers to a C1-C alkyl group linked through the carbon atom of the carbonyl (C=O) group. n Refers to an alkyl group.

[0035] As used herein, "C1-C n The term "-alkoxycarbonyl" refers to a C1-C alkoxycarbonyl group linked through the carbon atom of the carbonyl (or C=O) group. n -refers to the alkoxy moiety.

[0036] As used herein, "C1-C n -Alkoxycarbonyl-C1-C n The term "-alkyl" refers to C1-C n -C1-C substituted with alkoxycarbonyl group n -refers to alkyl radicals.

[0037] As used herein, the term "benzoyl" refers to a phenyl group attached through the carbon atom of a carbonyl (C=O) group.

[0038] As used herein, "C1-C n The term "haloalkoxycarbonyl" refers to a C1-C alkoxy group linked through the carbon atom of a carbonyl (C=O) group. n -refers to a haloalkoxy group.

[0039] As used herein, "C2-C n The term "-alkenyloxycarbonyl" refers to a C-C alkyl group linked through the carbon atom of a carbonyl (C=O) group. n -refers to an alkenyloxycarbonyl group.

[0040] As used herein, "C1-C n The term "-alkylaminocarbonyl" refers to a C1-C aryl group linked through the carbon atom of a carbonyl (C=O) group. n -Alkylamino group (or R aNHC(=O)-, (wherein R a However, C1~C n -alkyl groups).

[0041] As used herein, "aminocarbonyl-C1-C n The term "-alkyl" refers to a C1-C4 alkyl group substituted with an aminocarbonyl (or NHC(=O)-) group. n -refers to alkyl radicals.

[0042] As used herein, "C1-C n -Alkylaminocarbonyl-C1-C n The term "-alkyl" refers to C1-C n -alkylaminocarbonyl (or R a NHC(=O)-) group (wherein R a However, C1~C n -C alkyl group) n -Alkyl radicals. C1-C linked to nitrogen. n The alkyl group may be substituted.

[0043] As used herein, "NC 1-n The term "alkylamino" refers to a group of the formula -NH-R a (In the formula, R a is C as defined above 1-n It refers to the radical of (which is an alkyl radical).

[0044] As used herein, "N,N-diC" 1-n The term "alkylamino" refers to a group of the formula -N(R a )R a (In the formula, each R a may be the same or different C as defined above 1-n It refers to the radical of (which is an alkyl radical).

[0045] As used herein, "C1-C n -Alkylcarbonyloxy-C1~C nThe term "-alkyl" refers to C1-C n -alkylcarbonyloxy (or R a C(=O)O-) group (in the formula, R a However, C1~C n -haloalkyl group) n -refers to alkyl radicals.

[0046] As used herein, "C1-C n -Alkoxycarbonyloxy-C1~C n The term "-alkyl" refers to C1-C n -alkoxycarbonyloxy (or R c C(=O)O-) group (in the formula, R c However, C1~C n -alkoxy group) n -refers to an alkyl radical. A C1-Cn-alkoxy group attached to a nitrogen atom may be substituted.

[0047] As used herein, the term “N—C1-C4 alkoxy-C—C1-C4 alkyl-carbonimidoyl” refers to a group of the formula —C(R a )=NO(R b )(wherein, R a is a C1-C4 alkyl radical as generally defined above, and R b is a C1-C4 alkyl radical as generally defined above.

[0048] As used herein, the term “N-hydroxy-C—Ci-C4 alkyl-carbonimidoyl” refers to a group of the formula —C(R a )=NOH(where R a is a C1-C4 alkyl radical as generally defined above.

[0049] As used herein, the term "heterocyclyl" refers to a stable 3-, 4-, 5-, or 6-membered non-aromatic monocyclic ring radical containing one, two, or three heteroatoms / groups individually selected from nitrogen, oxygen, sulfur, S=O, and SO. The heterocyclyl radical can be attached to the remainder of the molecule via a carbon atom or a heteroatom. Examples of heterocycloalkyl radicals include, but are not limited to, epoxide, aziridinyl, pyrrolinyl, pyrrolidyl, tetrahydrofuranyl, tetrahydrothienyl, tetrahydrothiopyranyl, piperidyl, piperazinyl, tetrahydropyranyl, dioxolanyl, morpholinyl, oxazinanyl, oxetanyl, 1,1-dioxothiethan-3-yl, or δ-lactamyl. Heterocycloalkyl radicals may be substituted on the heteroatoms and / or carbon atoms. The term "saturated or partially saturated heterocycle" is understood to mean both monocyclic and bicyclic ring systems, as well as saturated and partially unsaturated heterocycles.

[0050] As used herein, the term "heteroaryl" refers to a 5- or 6-membered aromatic monocyclic ring group containing 1, 2, 3, or 4 heteroatoms individually selected from N, O, and S. Examples of heteroaryl include, but are not limited to, furanyl, pyrrolyl, thienyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, triazolyl, tetrazolyl, pyrazinyl, pyridazinyl, pyrimidyl, or pyridyl. "Heteroaryl-C1-C n -alkyl" or "heteroaryl-C3-C n The term "-cycloalkyl" refers to any C1-C4 alkyl group substituted with a heteroaryl group. n -Alkyl or C3-C n -refers to cycloalkyl radicals. Heteroaryl-C1-C n -Alkyl or Heteroaryl-C3-C n -Cycloalkyl radicals may be optionally substituted on the heteroaryl, alkyl and / or cycloalkyl groups.

[0051] As used herein, the term "control" refers to reducing the number of pests, eradicating pests and / or preventing further pest damage, such that damage to plants or plant-derived products is reduced.

[0052] As used herein, the term "pest" refers to insects and mollusks found in agriculture, horticulture, forestry, storage of plant-based products (such as fruit, grain, and lumber), and pests associated with damage to man-made structures. The term pest encompasses all stages in the life cycle of a pest.

[0053] As used herein, the term "effective amount" refers to the amount of a compound or salt thereof that produces a desired effect upon one or more applications.

[0054] An effective amount is readily determined by one skilled in the art using known techniques and by observing results obtained under analogous circumstances. In determining an effective amount, several factors are taken into consideration, including, but not limited to, the type of plant or derived product to which it is applied; the pest to be controlled and its life cycle; the particular compound applied; the type of application; and other relevant circumstances.

[0055] As used herein, the terms "room temperature" or "RT" or "rt" or "ambient temperature" refer to a temperature of about 15° C. to about 35° C. For example, rt can refer to a temperature of about 20° C. to about 30° C.

[0056] The following list refers to compounds of formula (I) of the present invention and defines substituent R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , B 1 , B 2 , W and Z 1For any one of these substituents, any definition given below can be combined with any definition of any other substituent given below or elsewhere in this specification.

[0057] In one embodiment of the present invention, R 1 is selected from the group consisting of hydrogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, or C3-C6-cycloalkyl. 1 is C1-C4 alkyl. Preferably, R 1 is methyl, ethyl or isopropyl. More preferably, R 1 is methyl.

[0058] In one embodiment of the invention, R2 is selected from the group consisting of hydrogen, halogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-haloalkyl, C3-C6-cycloalkyl, C1-C4-alkylcarbonyl, N-C1-C4 alkoxy-C-C1-C4 alkyl-carbonimidoyl, N-hydroxy-C-C1-C4 alkyl-carbonimidoyl, or C1-C4-alkoxycarbonyl. 2 is hydrogen, halogen, C1-C4 alkyl, C3-C6 cycloalkyl, C1-C4 alkylcarbonyl, N-C1-C4 alkoxy-C1-C4 alkyl-carbonimidoyl, or N-hydroxy-C1-C4 alkyl-carbonimidoyl. 2 is hydrogen, halogen, methyl, ethyl, cyclopropyl, C1-C2 alkylcarbonyl, N-C1-C2 alkoxy-C-C1-C2 alkyl-carbonimidoyl, or N-hydroxy-C-C1-C2 alkyl-carbonimidoyl. More preferably, R 2 is hydrogen, fluorine, chlorine, bromine, methyl, ethyl, cyclopropyl, acetyl, -C(CH3)=NOCH3, -C(CH3)=NOCH2CH3, or -C(CH3)=NOH. In a preferred embodiment of the present invention, R 2is selected from hydrogen, halogen, or C1-C4 alkyl. Most preferably, R 2 is hydrogen, chlorine, or methyl. In one preferred embodiment, R 2 is hydrogen. In another preferred embodiment, R 2 is methyl. In yet another preferred embodiment, R 2 is chlorine.

[0059] In one embodiment, R 3 is selected from hydrogen, halogen, C1-C4 haloalkyl, or C1-C4 alkyl. Preferably, R 3 is hydrogen or C1-C4 alkyl. More preferably, R 3 is hydrogen or methyl. Most preferably, R 3 is hydrogen.

[0060] In one embodiment of the present invention, R 4 is selected from hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl, or C3-C6-cycloalkyl. 4 is hydrogen, chlorine, bromine, fluorine, methyl, ethyl, trifluoromethyl, difluoromethyl, or cyclopropyl. More preferably, R 4 is hydrogen, chlorine, bromine, or methyl. Even more preferably, R 4 is hydrogen or methyl. Most preferably, R 4 is hydrogen. In one embodiment of the present invention, R 4 is hydrogen. In another embodiment of the present invention, R 4 is methyl.

[0061] In one embodiment of the present invention, R 5 and R 6 are independently selected from hydrogen or C1-C4-alkyl. Preferably, R 5 and R 6 are independently selected from hydrogen, methyl, or ethyl. More preferably, R 5 and R 6is independently selected from hydrogen or methyl. Even more preferably, R 5 and R 6 is hydrogen.

[0062] In one embodiment, R 7 is selected from hydrogen, C1-C4 alkyl, C1-C4-alkylcarbonyl, N-C1-C4 alkoxy-C-C1-C4 alkyl-carbonimidoyl, N-hydroxy-C-C1-C4-alkyl-carbonimidoyl, C1-C4-alkoxycarbonyl, N-methoxy-N-methyl-carbonyl, C1-C4 alkylaminocarbonyl, di(C1-C4 alkylamino)carbonyl, phenyl, 5- to 6-membered heteroaryl, or C3-C6-cycloalkyl, wherein said 5- to 6-membered heteroaryl are individually selected from N, O, and S. , 2, 3 or 4 heteroatoms, with the proviso that only one is O or S, wherein said phenyl and 5- to 6-membered heteroaryl are unsubstituted or substituted with 1 to 3 substituents independently selected from halogen, C1-C4 haloalkyl, cyano, carboxy, C1-C4 alkyl or C1-C4 alkoxy, and said C3-C6-cycloalkyl is unsubstituted or substituted with 1 to 3 substituents independently selected from halogen, C1-C4 haloalkyl, cyano, C1-C4 alkyl or C1-C4 alkoxy.

[0063] In another embodiment of the present invention, R 7is selected from the group consisting of hydrogen, C1-C4 alkyl, C3-C1-C4 alkylcarbonyl, C1-C4 alkoxycarbonyl, N-C1-C4 alkoxy-C-C1-C4 alkyl-carbonimidoyl, N-hydroxy-C-C1-C4 alkyl-carbonimidoyl, N-methoxy-N-methyl-carbonyl, C1-C4 alkylaminocarbonyl, di(C1-C4 alkylamino)carbonyl, phenyl, 5- to 6-membered heteroaryl, or C3-C6-cycloalkyl, wherein the 5- to 6-membered heteroaryl contains one heteroatom selected from N, and the phenyl and 5- to 6-membered heteroaryl are unsubstituted or substituted with one to two substituents independently selected from halogen, C1-C4 haloalkyl, cyano, or C1-C4 alkyl, and the C3-C6-cycloalkyl is unsubstituted or substituted with one substituent selected from cyano. Preferably, R 7 is selected from hydrogen, methyl, acetyl, -C(CH3)=NOCH3, -C(CH3)=NOCH2CH3, -C(CH3)=NOH, methoxycarbonyl, ethoxycarbonyl, N-methoxy-N-methyl-carbonyl, methylaminocarbonyl, dimethylaminocarbonyl, phenyl, 2-cyanophenyl, 3-cyanophenyl, 4-cyanophenyl, [4-(trifluoromethyl)pyrazol-1-yl], [3-(trifluoromethyl)pyrazol-1-yl], 3-cyanopyrazol-1-yl, 4-cyanopyrazol-1-yl, 5-chloropyrazol-1-yl, 5-fluoropyrazol-1-yl), 3,5-dimethylpyrazol-1-yl, 5-methylpyrazol-1-yl, pyrazol-1-yl, cyclopropyl, or 1-cyanocyclopropyl. More preferably, R 7 is selected from hydrogen, methyl, acetyl, C(CH3)=NOCH3, -C(CH3)=NOCH2CH3, -C(CH3)=NOH, phenyl, 4-cyanophenyl, pyrazol-1-yl, cyclopropyl, or 1-cyanocyclopropyl. Even more preferably, R 7 is selected from hydrogen, methyl, cyclopropyl, or 1-cyanocyclopropyl.

[0064] In another embodiment, R 7 is selected from hydrogen, C1-C4 alkyl, or C3-C6-cycloalkyl. 7 is hydrogen, methyl, cyclopropyl, or 1-cyanocyclopropyl. Even more preferably, R 7 is hydrogen, methyl, or cyclopropyl.

[0065] In another preferred embodiment, R 7 is C1-C4 alkyl. Preferably, R 7 is methyl or ethyl. More preferably, R 7 is methyl.

[0066] In one embodiment of the present invention, R 8 , R 9 , R 10 and R 11 is hydrogen, halogen, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkenyloxy, C2-C4 alkynyloxy, C1-C4 alkylsulfanyl, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4 alkoxy-C1-C4 alkyl, N-C1-C4-alkylamino, N,N-di(C1-C4-alkyl)amino, C1-C4 alkoxycarbonyl, C1-C4 alkylcarbonyl, N-C1-C4 alkoxy-C1-C4 alkyl-carbonimidoyl, N-hydroxy-C1-C4 alkyl-carbonyl and each of the phenyl, 5- to 6-membered heteroaryl, and C3-C6 cycloalkyl is independently selected from the group consisting of phenylimidoyl, hydroxy, trifluoromethylsulfonyloxy, cyano, carboxy, amino, phenyl, 5- to 6-membered heteroaryl, or C3-C6 cycloalkyl, wherein the 5- to 6-membered heteroaryl contains 1, 2, 3, or 4 heteroatoms individually selected from N, O, and S, with the proviso that only one is O or S, and any of the phenyl, 5- to 6-membered heteroaryl, and C3-C6 cycloalkyl is optionally substituted with 1, 2, or 3 substituents independently selected from halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, or C1-C4 alkoxy.

[0067] In one embodiment of the present invention, R 8 and R 9 are independently selected from hydrogen, halogen, cyano, C1-C4 alkyl, or C1-C4 alkoxy. 8 and R 9 are independently selected from hydrogen, halogen, methyl, methoxy, or cyano. More preferably, R 8 and R 9 are independently selected from hydrogen, methyl, chlorine, fluorine, bromine, or methoxy. Even more preferably, R 8 and R 9 is independently selected from hydrogen or methoxy.

[0068] In another embodiment of the present invention, R 8 is hydrogen, halogen, or cyano. Preferably, R 8 is hydrogen, bromine, chlorine, or cyano. More preferably, R 8 is hydrogen, cyano, or bromine. Even more preferably, R 8 is hydrogen.

[0069] In another embodiment, R 9is hydrogen, halogen, C1-C3 alkyl, C1-C2 haloalkyl, C1-C3 haloalkoxy, C1-C4 alkoxy, C1-C3 alkenyloxy, C1-C3 alkynyloxy, C1-C2 alkylsulfanyl, C1-C2 alkylsulfinyl, C1-C2 alkylsulfonyl, C1-C2 alkoxy-C1-C2 alkyl, C1-C3 alkoxycarbonyl, C1-C2 alkylcarbonyl, N-C1-C2 alkoxy-C-C1-C2 alkyl-carbonimidoyl, N-hydroxy-C-C1-C2 alkyl-carbonimidoyl, hydroxy, C1-C2 alkylaminocarbonyl, di(C1-C2 alkylamino)carbonyl, trifluoromethylsulfonyloxy, cyano, carboxy, phenyl, 2-cyanophenyl, 3- cyanophenyl, 4-cyanophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, [4-(trifluoromethyl)pyrazol-1-yl], [3-(trifluoromethyl)pyrazol-1-yl], 3-cyanopyrazol-1-yl, 4-cyanopyrazol-1-yl, 5-chloropyrazol-1-yl, 4-chloropyrazol-1-yl, 3-chloropyrazol-1-yl, 5-fluoropyrazol-1-yl, 4-fluoropyrazol-1-yl, 3-fluoropyrazol-1-yl, 3,5-dimethylpyrazol-1-yl, 5-methylpyrazol-1-yl, 4-methylpyrazol-1-yl, 3-methylpyrazol-1-yl, pyrazol-1-yl, cyclopropyl, or 1-cyanocyclopropyl. Preferably, R 9is hydrogen, chloro, fluoro, bromo, methyl, ethyl, trifluoromethyl, difluoromethyl, difluoromethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, methoxy, ethoxy, propoxy, allyloxy, prop-2-ynoxy, methylsulfanyl, methylsulfinyl, methylsulfonyl, methoxymethyl, ethoxymethyl, 2-methoxyethoxymethyl, methoxycarbonyl, ethoxycarbonyl, tert-butoxycarbonyl, acetyl, propanoyl, -C(CH3)=NOCH3, -C(CH3)=NOCH2CH3, -C(CH3)=NOH, methylaminocarbonyl, di(methylamino)carbonyl, trifluoromethylsulfonyloxy, cyano, carboxy, phenyl, 2-cyanophenyl , 3-cyanophenyl, 4-cyanophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, [4-(trifluoromethyl)pyrazol-1-yl], [3-(trifluoromethyl)pyrazol-1-yl], 3-cyanopyrazol-1-yl, 4-cyanopyrazol-1-yl, 5-chloropyrazol-1-yl, 4-chloropyrazol-1-yl, 3-chloropyrazol-1-yl, 5-fluoropyrazol-1-yl, 4-fluoropyrazol-1-yl, 3-fluoropyrazol-1-yl, 3,5-dimethylpyrazol-1-yl, 5-methylpyrazol-1-yl, 4-methylpyrazol-1-yl, 3-methylpyrazol-1-yl, pyrazol-1-yl, cyclopropyl, or 1-cyanocyclopropyl. More preferably, R 9is hydrogen, chloro, bromo, fluoro, cano, methyl, methoxy, propoxy, allyloxy, methoxymethyl, 2-methoxyethoxymethyl, phenyl, 2-cyanophenyl, 3-cyanophenyl, 4-cyanophenyl, [4-(trifluoromethyl)pyrazol-1-yl], [3-(trifluoromethyl)pyrazol-1-yl], 3-cyanopyrazol-1-yl, 4-cyanopyrazol-1-yl, 5-chloropyrazol-1-yl, 4-chloropyrazol-1-yl, 3-chloropyrazol-1-yl, 5-fluoropyrazol-1-yl, 4-fluoropyrazol-1-yl, 3-fluoropyrazol-1-yl, 3,5-dimethylpyrazol-1-yl, 5-methylpyrazol-1-yl, 4-methylpyrazol-1-yl, 3-methylpyrazol-1-yl, pyrazol-1-yl, cyclopropyl, or 1-cyanocyclopropyl. Even more preferably, R 9 is hydrogen, chloro, bromo, cyano, methyl, or methoxy. Most preferably, R 9 is hydrogen or methoxy.

[0070] In one embodiment of the present invention, B 1 is CR 10 and B 2 is CR 11 or B 1 is N and B 2 is CR 11 or B 1 is CR 10 and B 2 is N. Preferably, B 1 is CR 10 and B 2 is CR 11 is.

[0071] In one embodiment of the present invention, R 10 and R 11is hydrogen, halogen, hydroxy, cyano, amino, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkenyloxy, C2-C4 alkynyloxy, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkoxy-C1-C4 alkyl, N-C1-C4-alkylamino, N,N-di(C1-C4-alkyl)amino, C1-C4 alkoxycarbonyl, C1-C4 alkylcarbonyl, N-C1-C4 alkoxy-C1-C4 alkyl-carbonimidoyl, N-hydroxy-C1-C4 alkyl-carbonimidoyl, alkyl-C=N-OR X (X=(CH2)n-CN), hydroxy, trifluoromethylsulfonyloxy, carboxy, phenyl, 5- to 6-membered heteroaryl, and C3-C6 cycloalkyl, wherein the 5- to 6-membered heteroaryl contains 1, 2, 3, or 4 heteroatoms individually selected from N, O, and S, with the proviso that only one is O or S, and any of the phenyl, 5- to 6-membered heteroaryl, and C3-C6 cycloalkyl may be optionally substituted by 1, 2, or 3 substituents independently selected from halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, or C1-C4 alkoxy. Preferably, R 10 and R 11is hydrogen, chloro, fluoro, bromo, methyl, ethyl, trifluoromethyl, difluoromethyl, difluoromethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, methoxy, ethoxy, propoxy, allyloxy, prop-2-ynoxy, methylsulfanyl, methylsulfinyl, methylsulfonyl, methoxymethyl, ethoxymethyl, 2-methoxyethoxymethyl, methoxycarbonyl, ethoxycarbonyl, tert-butoxycarbonyl, acetyl, propanoyl, -C(CH3)=NOCH3, -C(CH3)=NOCH2CH3, -C(CH3)=NOH, methylaminocarbonyl, di(methylamino)carbonyl, trifluoromethylsulfonyloxy, cyano, carboxy, phenyl, 2-cyanophenyl, 3-cyano More preferably, R is independently selected from aryl, 4-cyanophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, [4-(trifluoromethyl)pyrazol-1-yl], [3-(trifluoromethyl)pyrazol-1-yl], 3-cyanopyrazol-1-yl, 4-cyanopyrazol-1-yl, 5-chloropyrazol-1-yl, 4-chloropyrazol-1-yl, 3-chloropyrazol-1-yl, 5-fluoropyrazol-1-yl, 4-fluoropyrazol-1-yl, 3-fluoropyrazol-1-yl, 3,5-dimethylpyrazol-1-yl, 5-methylpyrazol-1-yl, 4-methylpyrazol-1-yl, 3-methylpyrazol-1-yl, pyrazol-1-yl, cyclopropyl, or 1-cyanocyclopropyl. 10 and R 11is hydrogen, chloro, bromo, fluoro, cyano, methyl, methoxy, propoxy, allyloxy, methoxymethyl, 2-methoxyethoxymethyl, phenyl, 2-cyanophenyl, 3-cyanophenyl, 4-cyanophenyl, [4-(trifluoromethyl)pyrazol-1-yl], [3-(trifluoromethyl)pyrazol-1-yl], 3-cyanopyrazol-1-yl, 4-cyanopyrazol-1-yl, 5-chloropyrazol-1-yl, 4-chloropyrazol-1-yl, 3- and independently selected from chloropyrazol-1-yl, 5-fluoropyrazol-1-yl, 4-fluoropyrazol-1-yl, 3-fluoropyrazol-1-yl, 3,5-dimethylpyrazol-1-yl, 5-methylpyrazol-1-yl, 4-methylpyrazol-1-yl, 3-methylpyrazol-1-yl, pyrazol-1-yl, C(CH3)=NOCH3, -C(CH3)=NOCH2CH3, -C(CH3)=NOH, cyclopropyl, or 1-cyanocyclopropyl. Even more preferably, R 10 and R 11 are independently selected from hydrogen, chlorine, bromine, or cyano.

[0072] In another embodiment, R 10 and R 11 are independently selected from hydrogen, halogen, C1-C3 alkyl, or C1-C4 alkoxy. 10 and R 11 are independently selected from hydrogen or halogen. More preferably, R 10 and R 11 is hydrogen, bromine, or chlorine. Even more preferably, R 10 and R 11 is hydrogen.

[0073] In one embodiment of the present invention, W is O, N, S, *—CH2O— # , *-CH2NH- # , *-CH2S- # , or *-CH2- # wherein the star (*) indicates the position of the link to the carbonyl group, and # indicates Z 1Preferably, W is O, N, -CH2O- # , *-CH2NH- # , *-CH2S- # , or *-CH2- # wherein the star (*) indicates the position of the link to the carbonyl group, and # indicates Z 1 More preferably, W is O, N, or -CH2O-. # , *-CH2NH- # , or *-CH2- # wherein the star (*) indicates the position of the link to the carbonyl group, and # indicates Z 1 Preferably, W is O, N, or -CH2-. # ,- # wherein the star (*) indicates the position of the link to the carbonyl group, and # indicates Z 1 Indicates the position where it is connected to.

[0074] In another embodiment, W is selected from O. In yet another embodiment, W is selected from N. In yet another embodiment, W is -CH2- # ,- # where the star (*) indicates the position of the link to the carbonyl group, and # indicates Z 1 Indicates the position where it is connected to.

[0075] In one embodiment of the present invention, W is O, N, S, *—CH2O— # , *-CH2NH- # , *-CH2S- # or a bond, where the star (*) indicates the position of the link to the carbonyl group, and # indicates Z 1 Preferably, W is O, N, -CH2O- # , *-CH2NH- # , *-CH2S- # or a bond, where the star (*) indicates the position of the link to the carbonyl group, and # indicates Z 1 More preferably, W is O, N, or -CH2O-.# , *-CH2NH- # or a bond, where the star (*) indicates the position of the link to the carbonyl group, and # indicates Z 1 Preferably, W is selected from O, N, or a bond.

[0076] In another embodiment, W is selected from O. In yet another embodiment, W is selected from N. In yet another embodiment, W is a bond.

[0077] In one embodiment, Z 1is selected from C1-C6 alkyl, phenyl, or 5- to 6-membered heteroaryl, wherein the C1-C6 alkyl is unsubstituted or selected from halogen, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkenyloxy, C2-C4 alkynyloxy, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkoxy-C1-C4 alkyl , C1-C4 alkoxycarbonyl, C1-C4 alkylcarbonyl, N-C1-C4 alkoxy-C-C1-C4 alkyl-carbonimidoyl, N-hydroxy-C-C1-C4 alkyl-carbonimidoyl, hydroxy, trifluoromethylsulfonyloxy, cyano, carboxy, phenyl, 5- to 6-membered saturated or partially saturated heterocycle, 5- to 6-membered heteroaryl and C3-C6-cycloalkyl, any of the 5- to 6-membered heteroaryls contains 1, 2 or 3 identical or different heteroatoms selected from N, O or S, provided that only one is O or S; any of the 5- to 6-membered saturated or partially saturated heterocyclic rings contains 1, 2 or 3 identical or different heteroatoms selected from N, O or S, provided that only one is O or S; any of the phenyls, any of the 5- to 6-membered heteroaryls, and any of the 5- to 6-membered saturated or partially saturated heterocyclic rings is unsubstituted or not substituted by a halogen atom; and is substituted with one, two, three or up to the maximum possible number of the same or different substituents selected from the group consisting of halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6-cycloalkyl, and C1-C4 alkoxy, any of said C3-C6-cycloalkyl being unsubstituted or substituted with one, two, three or up to the maximum possible number of the same or different substituents selected from the group consisting of halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, and C1-C4 alkoxy.

[0078] Preferably, Z 1is selected from C1-C6 alkyl, phenyl, or 5- to 6-membered heteroaryl, wherein the C1-C6 alkyl is unsubstituted or substituted with 1, 2 or 3 identical or different substituents selected from the group consisting of halogen, C1-C4 alkyl, C1-C4 haloalkyl, phenyl, 5- to 6-membered heteroaryl, and C3-C6-cycloalkyl, wherein any of the 5- to 6-membered heteroaryls contains 1 or 2 identical or different heteroatoms selected from N or O, and any of the phenyls and any of the 5- to 6-membered heteroaryls is unsubstituted or substituted with 1 or 2 identical or different substituents selected from the group consisting of halogen, cyano, C1-C4 alkyl, and C3-C6-cycloalkyl.

[0079] More preferably, Z 1 is selected from C1-C6 alkyl, phenyl, or 5- to 6-membered heteroaryl, wherein the C1-C6 alkyl is unsubstituted or substituted with 1, 2 or 3 identical or different substituents selected from the group consisting of chlorine, fluorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, and 5- to 6-membered heteroaryl, wherein any of the 5- to 6-membered heteroaryls contains 1 or 2 identical or different heteroatoms selected from N or O, and any of the phenyls and any of the 5- to 6-membered heteroaryls is unsubstituted or substituted with 1 or 2 identical or different substituents selected from the group consisting of chlorine, bromine, fluorine, cyano, methyl, ethyl, and cyclopropyl.

[0080] More preferably, Z 1is selected from C1-C6 alkyl, phenyl, or 5- or 6-membered heteroaryl, wherein the C1-C6 alkyl is unsubstituted or substituted with 1, 2, or 3 identical or different substituents selected from the group consisting of chlorine, fluorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, cyclopropyl, cyclohexyl, phenyl, and 6-membered heteroaryl, and the 5- or 6-membered heteroaryl and the 6-membered heteroaryl contain one heteroatom selected from N, and any of the phenyl, the 5- or 6-membered heteroaryl, and the 6-membered heteroaryl is unsubstituted or substituted with 1 or 2 identical or different substituents selected from the group consisting of chlorine, bromine, fluorine, cyano, methyl, ethyl, and cyclopropyl.

[0081] More preferably, Z 1 is selected from C1-C6 alkyl, phenyl, 2,4-difluorophenyl, 3,5-difluoro-2-furyl, 3-fluoro-2-furyl, 5-fluoro-2-furyl, 3,5-difluoro-2-thienyl, 3-fluoro-2-thienyl, 5-fluoro-2-thienyl, 2-fluorophenyl, 4-fluorophenyl, 3-fluoro-2-pyridyl, 5-fluoro-2-pyridyl, 3,4-difluoro-2-pyridyl, 3,5-difluoro-2-pyridyl, 4-fluoropyridazin-3-yl, 4,5-difluoropyridazin-3-yl, and 5-fluoropyridazin-4-yl. wherein the C1-C6 alkyl is unsubstituted or substituted with one or two identical or different substituents selected from the group consisting of chlorine, fluorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, cyclopropyl, cyclohexyl, phenyl, and 6-membered heteroaryl, and the 6-membered heteroaryl contains one heteroatom selected from N, and the phenyl and the 6-membered heteroaryl are unsubstituted or substituted with one or two identical or different substituents selected from the group consisting of chlorine, bromine, fluorine, cyano, methyl, ethyl, and cyclopropyl.

[0082] In another embodiment, Z 1is selected from C1-C6 alkyl, phenyl, 2,4-difluorophenyl, 3,5-difluoro-2-furyl, 3-fluoro-2-furyl, 5-fluoro-2-furyl, 3,5-difluoro-2-thienyl, 3-fluoro-2-thienyl, 5-fluoro-2-thienyl, 2-fluorophenyl, 4-fluorophenyl, 3-fluoro-2-pyridyl, 5-fluoro-2-pyridyl, 3,4-difluoro-2-pyridyl, 3,5-difluoro-2-pyridyl, 4-fluoropyridazin-3-yl, 4,5-difluoropyridazin-3-yl, and 5-fluoropyridazin-4-yl; wherein the C1-C6 alkyl is unsubstituted or substituted with one or two identical or different substituents selected from the group consisting of chlorine, fluorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, cyclopropyl, cyclohexyl, phenyl, and 6-membered heteroaryl, and the 6-membered heteroaryl contains one heteroatom selected from N, and the phenyl and the 6-membered heteroaryl are unsubstituted or substituted with one or two identical or different substituents selected from the group consisting of chlorine, bromine, fluorine, cyano, methyl, ethyl, and cyclopropyl.

[0083] In another preferred embodiment, Z 1is selected from C1-C6 alkyl, phenyl, 2,4-difluorophenyl, 3,5-difluoro-2-furyl, 3-fluoro-2-furyl, 5-fluoro-2-furyl, 3,5-difluoro-2-thienyl, 3-fluoro-2-thienyl, 5-fluoro-2-thienyl, 2-fluorophenyl, 4-fluorophenyl, 3-fluoro-2-pyridyl, 5-fluoro-2-pyridyl, 3,4-difluoro-2-pyridyl, 3,5-difluoro-2-pyridyl, 4-fluoropyridazin-3-yl, 4,5-difluoropyridazin-3-yl, and 5-fluoropyridazin-4-yl, wherein the C1-C6 alkyl is unsubstituted or selected from chlorine, fluorine, bromine, methyl, ethyl, trifluoromethyl and substituted by one or two identical or different substituents selected from the group consisting of phenyl, difluoromethyl, cyclopropyl, cyclohexyl, phenyl, 2,4-difluorophenyl, 3,5-difluoro-2-furyl, 3-fluoro-2-furyl, 5-fluoro-2-furyl, 3,5-difluoro-2-thienyl, 3-fluoro-2-thienyl, 5-fluoro-2-thienyl, 2-fluorophenyl, 4-fluorophenyl, 3-fluoro-2-pyridyl, 5-fluoro-2-pyridyl, 3,4-difluoro-2-pyridyl, 3,5-difluoro-2-pyridyl, 4-fluoropyridazin-3-yl, 4,5-difluoropyridazin-3-yl, and 5-fluoropyridazin-4-yl.

[0084] In one embodiment of the present invention, Z 1is selected from C1-C6 alkyl, phenyl, or 6-membered heteroaryl, wherein the C1-C6 alkyl is unsubstituted or substituted with halogen, C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 haloalkyl, C1-C4 alkoxy, C1-C4 haloalkoxy, C2-C4 alkenyloxy, C2-C4 alkynyloxy, C1-C4 alkylsulfanyl, C1-C4 alkylsulfinyl, C1-C4 alkylsulfonyl, C1-C4 alkoxy-C1-C4 alkyl, C1-C4 alkoxy and substituted by one, two, or three identical or different substituents selected from the group consisting of alkoxycarbonyl, C1-C4 alkylcarbonyl, N-C1-C4 alkoxy-C-C1-C4 alkyl-carbonimidoyl, N-hydroxy-C-C1-C4 alkyl-carbonimidoyl, hydroxy, trifluoromethylsulfonyloxy, cyano, carboxy, phenyl, a 5- to 6-membered saturated or partially saturated heterocycle, a 5- to 6-membered heteroaryl, and a C3-C6-cycloalkyl, and the 6-membered heteroaryl and the 5- to 6-membered heteroaryl are substituted by one, two, or three identical or different substituents selected from the group consisting of alkoxycarbonyl, C1-C4 alkylcarbonyl, N-C1-C4 alkoxy-C-C1-C4 alkyl-carbonimidoyl, N-hydroxy-C-C1-C4 alkyl-carbonimidoyl, hydroxy, trifluoromethylsulfonyloxy, cyano, carboxy, phenyl, a 5- to 6-membered saturated or partially saturated heterocycle, a 5- to 6-membered heteroaryl, and a C3-C6-cycloalkyl. any of the 5- to 6-membered heteroaryls contains 1, 2 or 3 of the same or different heteroatoms selected from N, O or S, provided that only one is O or S; any of the 5- to 6-membered saturated or partially saturated heterocyclic rings contains 1, 2 or 3 of the same or different heteroatoms selected from N, O or S, provided that only one is O or S; any of the phenyls, any of the 6-membered heteroaryls, any of the 5- to 6-membered heteroaryls, and any of the 5- to 6-membered saturated or partially saturated heterocyclic rings is unsubstituted; or or substituted with 1, 2, 3 or up to the maximum possible number of the same or different substituents selected from the group consisting of halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6-cycloalkyl and C1-C4 alkoxy, any of said C3-C6-cycloalkyl being unsubstituted or substituted with 1, 2, 3 or up to the maximum possible number of the same or different substituents selected from the group consisting of halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl and C1-C4 alkoxy.

[0085] Preferably, Z 1is selected from C1-C6 alkyl, phenyl, or 6-membered heteroaryl, wherein the C1-C6 alkyl is unsubstituted or substituted with 1, 2 or 3 identical or different substituents selected from the group consisting of halogen, C1-C4 alkyl, C1-C4 haloalkyl, phenyl, 5- to 6-membered heteroaryl, and C3-C6-cycloalkyl, wherein any of the 6-membered heteroaryl and 5- to 6-membered heteroaryl contains 1 or 2 identical or different heteroatoms selected from N or O, and any of the phenyls, any of the 6-membered heteroaryls, and any of the 5- to 6-membered heteroaryls is unsubstituted or substituted with 1 or 2 identical or different substituents selected from the group consisting of halogen, cyano, C1-C4 alkyl, and C3-C6-cycloalkyl.

[0086] More preferably, Z 1 is selected from C1-C6 alkyl, phenyl, or 6-membered heteroaryl, wherein the C1-C6 alkyl is unsubstituted or substituted with 1, 2 or 3 identical or different substituents selected from the group consisting of chlorine, fluorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, cyclopropyl, cyclohexyl, phenyl, and 6-membered heteroaryl, wherein either of the 6-membered heteroaryls contains 1 heteroatom selected from N, and either of the phenyl and the 6-membered heteroaryl is unsubstituted or substituted with 1 or 2 identical or different substituents selected from the group consisting of chlorine, bromine, fluorine, cyano, methyl, ethyl, and cyclopropyl.

[0087] In one embodiment of the present invention, Z 1is selected from C1-C6-alkyl, wherein the C1-C6-alkyl is unsubstituted or selected from halogen, C1-C4-alkyl, C2-C4-alkenyl, C2-C4-alkynyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C2-C4-alkenyloxy, C2-C4-alkynyloxy, C1-C4-alkylsulfanyl, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-alkoxy-C1-C4-alkyl, C1- and substituted by one, two, or three identical or different substituents selected from the group consisting of C4-alkoxycarbonyl, C1-C4-alkylcarbonyl, N-C1-C4 alkoxy-C-C1-C4 alkyl-carbonimidoyl, N-hydroxy-C-C1-C4 alkyl-carbonimidoyl, hydroxy, trifluoromethylsulfonyloxy, cyano, carboxy, phenyl, a 5- to 6-membered saturated or partially saturated heterocycle, a 5- to 6-membered heteroaryl, and a C3-C6-cycloalkyl, wherein the 5-membered Any of the 5- to 6-membered heteroaryls contains 1, 2, or 3 of the same or different heteroatoms selected from N, O, or S, provided that only one is O or S; any of the 5- to 6-membered saturated or partially saturated heterocyclic rings contains 1, 2, or 3 of the same or different heteroatoms selected from N, O, or S, provided that only one is O or S; any of the phenyls, any of the 5- to 6-membered heteroaryls, and any of the 5- to 6-membered saturated or partially saturated heterocyclic rings is unsubstituted or halogenated. , cyano, C1-C4 alkyl, C1-C4 haloalkyl, C3-C6-cycloalkyl and C1-C4 alkoxy, any of which is unsubstituted or substituted with 1, 2, 3 or up to the maximum possible number of the same or different substituents selected from the group consisting of halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl and C1-C4 alkoxy.

[0088] Preferably, Z 1is selected from C1-C6 alkyl, wherein the C1-C6 alkyl is unsubstituted or substituted with 1, 2 or 3 identical or different substituents selected from the group consisting of halogen, C1-C4 alkyl, C1-C4 haloalkyl, phenyl, 5- to 6-membered heteroaryl and C3-C6-cycloalkyl, wherein any of the 5- to 6-membered heteroaryls contains 1 or 2 identical or different heteroatoms selected from N or O, and any of the phenyls and any of the 5- to 6-membered heteroaryls is unsubstituted or substituted with 1 or 2 identical or different substituents selected from the group consisting of halogen, cyano, C1-C4 alkyl and C3-C6-cycloalkyl.

[0089] More preferably, Z 1 is selected from C1-C6 alkyl, wherein the C1-C6 alkyl is unsubstituted or substituted with 1, 2 or 3 identical or different substituents selected from the group consisting of chlorine, fluorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, cyclopropyl, cyclohexyl, phenyl and 6-membered heteroaryl, any of the 6-membered heteroaryls containing 1 heteroatom selected from N, and any of the phenyl and the 6-membered heteroaryls is unsubstituted or substituted with 1 or 2 identical or different substituents selected from the group consisting of chlorine, bromine, fluorine, cyano, methyl, ethyl and cyclopropyl.

[0090] Thus, the present invention provides R as defined above. 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , B 1 , B 2 , W and Z 1 Compounds of formula (I) having the formula:

[0091] Embodiments according to the present invention are provided as follows.

[0092] Preferably, in the compound of formula (I), R 1 is methyl, R 2 is hydrogen, chlorine, or methyl; R 3 is hydrogen; R 4 is hydrogen or methyl; R 5 and R 6 is hydrogen; R 7 is hydrogen, C1-C4 alkyl, or C3-C6-cycloalkyl; R 8 is hydrogen, bromine, chlorine, or cyano; R 9 is hydrogen, bromine, chlorine, cyano, methyl, or methoxy; B 1 is N or CR 10 (In the formula, R 10 is hydrogen, bromine, chlorine, or cyano); B 2 is N or CR 11 (In the formula, R 11 is hydrogen, bromine, chlorine, or cyano); and W and Z 1 is as defined for the compounds of formula (I) according to the invention.

[0093] Preferably, in the compound of formula (I), R 1 is methyl, R 2 is hydrogen, chlorine, or methyl; R 3 is hydrogen; R 4 is hydrogen or methyl; R 5 and R 6 is hydrogen; R 7is hydrogen, C1-C4 alkyl, or C3-C6-cycloalkyl; R 8 is hydrogen, bromine, chlorine, or cyano; R 9 is hydrogen, bromine, chlorine, cyano, methyl, or methoxy; B 1 is N or CR 10 (In the formula, R 10 is hydrogen, bromine, chlorine, or cyano); B 2 is N or CR 11 (In the formula, R 11 is hydrogen, bromine, chlorine, or cyano); W is O, N, *-CH2O- # , *-CH2NH- # or a bond, where the star (*) indicates the position of the link to the carbonyl group, and # indicates Z 1 indicates the position of connection to; and Z 1 is as defined for the compounds of formula (I) according to the invention.

[0094] Preferably, in the compound of formula (I), R 1 is methyl, R 2 is hydrogen, chlorine, or methyl; R 3 is hydrogen; R 4 is hydrogen or methyl; R 5 and R 6 is hydrogen; R 7 is hydrogen, C1-C4 alkyl, or C3-C6-cycloalkyl; R 8 is hydrogen, bromine, chlorine, or cyano; R 9 is hydrogen, bromine, chlorine, cyano, methyl, or methoxy; B 1 is N or CR 10 (In the formula, R 10is hydrogen, bromine, chlorine, or cyano); B 2 is N or CR 11 (In the formula, R 11 is hydrogen, bromine, chlorine, or cyano); W is O, N, *-CH2O- # , *-CH2NH- # , or *-CH2- # where the star (*) indicates the position of the link to the carbonyl group, and # indicates Z 1 indicates the position of connection to; and Z 1 is as defined for the compounds of formula (I) according to the invention.

[0095] Preferably, in the compound of formula (I), R 1 is methyl, R 2 is hydrogen, chlorine, or methyl; R 3 is hydrogen; R 4 is hydrogen or methyl; R 5 and R 6 is hydrogen; R 7 is hydrogen, C1-C4 alkyl, or C3-C6-cycloalkyl; R 8 is hydrogen, bromine, chlorine, or cyano; R 9 is hydrogen, bromine, chlorine, cyano, methyl, or methoxy; B 1 is N or CR 10 (In the formula, R 10 is hydrogen, bromine, chlorine, or cyano); B 2 is N or CR 11 (In the formula, R 11 is hydrogen, bromine, chlorine, or cyano); W is O, N, *-CH2O- # , *-CH2NH- # , *-CH2S-# or a bond, where the star (*) indicates the position of the link to the carbonyl group, and # indicates Z 1 indicates the position of connection to; and Z 1 is C1-C6 alkyl, phenyl, or 5- to 6-membered heteroaryl; said C1-C6 alkyl is unsubstituted or substituted with 1, 2, or 3 identical or different substituents selected from the group consisting of halogen, C1-C4 alkyl, C1-C4 haloalkyl, phenyl, 5- to 6-membered heteroaryl, and C3-C6-cycloalkyl; any of said 5- to 6-membered heteroaryls contains 1 or 2 identical or different heteroatoms selected from N or O; any of said phenyls and any of said 5- to 6-membered heteroaryls is unsubstituted or substituted with 1 or 2 identical or different substituents selected from the group consisting of halogen, cyano, C1-C4 alkyl, and C3-C6-cycloalkyl.

[0096] Preferably, in the compound of formula (I), R 1 is methyl, R 2 is hydrogen, chlorine, or methyl; R 3 is hydrogen; R 4 is hydrogen or methyl; R 5 and R 6 is hydrogen; R 7 is hydrogen, C1-C4 alkyl, or C3-C6-cycloalkyl; R 8 is hydrogen, bromine, chlorine, or cyano; R 9 is hydrogen, bromine, chlorine, cyano, methyl, or methoxy; B 1 is N or CR 10 (In the formula, R 10 is hydrogen, bromine, chlorine, or cyano); B 2 is N or CR 11(In the formula, R 11 is hydrogen, bromine, chlorine, or cyano); W is O, N, *-CH2O- # , *-CH2NH- # , *-CH2S- # or a bond, where the star (*) indicates the position of the link to the carbonyl group, and # indicates Z 1 indicates the position of connection to; and Z 1 is selected from C1-C6-alkyl, phenyl, or 6-membered heteroaryl; the C1-C6-alkyl is unsubstituted or substituted with 1, 2, or 3 identical or different substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, phenyl, 5- to 6-membered heteroaryl, and C3-C6-cycloalkyl; any of the 6-membered heteroaryl and the 5- to 6-membered heteroaryl contains 1 or 2 identical or different heteroatoms selected from N or O, and any of the phenyl, the 6-membered heteroaryl, and the 5- to 6-membered heteroaryl is unsubstituted or substituted with 1 or 2 identical or different substituents selected from the group consisting of halogen, cyano, C1-C4-alkyl, and C3-C6-cycloalkyl.

[0097] Preferably, in the compound of formula (I), R 1 is methyl, R 2 is hydrogen, chlorine, or methyl; R 3 is hydrogen; R 4 is hydrogen or methyl; R 5 and R 6 is hydrogen; R 7 is hydrogen, C1-C4 alkyl, or C3-C6-cycloalkyl; R 8 is hydrogen, bromine, chlorine, or cyano; R 9is hydrogen, bromine, chlorine, cyano, methyl, or methoxy; B 1 is N or CR 10 (In the formula, R 10 is hydrogen, bromine, chlorine, or cyano); B 2 is N or CR 11 (In the formula, R 11 is hydrogen, bromine, chlorine, or cyano); W is O, N, *-CH2O- # , *-CH2NH- # or a bond, where the star (*) indicates the position of the link to the carbonyl group, and # indicates Z 1 indicates the position of connection to; and Z 1 is C1-C6 alkyl, phenyl, or 5- to 6-membered heteroaryl; said C1-C6 alkyl is unsubstituted or substituted with 1, 2, or 3 identical or different substituents selected from the group consisting of halogen, C1-C4 alkyl, C1-C4 haloalkyl, phenyl, 5- to 6-membered heteroaryl, and C3-C6-cycloalkyl; any of said 5- to 6-membered heteroaryls contains 1 or 2 identical or different heteroatoms selected from N or O; any of said phenyls and any of said 5- to 6-membered heteroaryls is unsubstituted or substituted with 1 or 2 identical or different substituents selected from the group consisting of halogen, cyano, C1-C4 alkyl, and C3-C6-cycloalkyl.

[0098] Preferably, in the compound of formula (I), R 1 is methyl, R 2 is hydrogen, chlorine, or methyl; R 3 is hydrogen; R 4 is hydrogen or methyl; R 5 and R 6 is hydrogen; R 7is hydrogen, C1-C4 alkyl, or C3-C6-cycloalkyl; R 8 is hydrogen, bromine, chlorine, or cyano; R 9 is hydrogen, bromine, chlorine, cyano, methyl, or methoxy; B 1 is N or CR 10 (In the formula, R 10 is hydrogen, bromine, chlorine, or cyano); B 2 is N or CR 11 (In the formula, R 11 is hydrogen, bromine, chlorine, or cyano); W is O, N, *-CH2O- # , *-CH2NH- # or a bond, where the star (*) indicates the position of the link to the carbonyl group, and # indicates Z 1 indicates the position of connection to; and Z 1 is selected from C1-C6-alkyl, phenyl, or 6-membered heteroaryl; the C1-C6-alkyl is unsubstituted or substituted with 1, 2, or 3 identical or different substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, phenyl, 5- to 6-membered heteroaryl, and C3-C6-cycloalkyl; any of the 6-membered heteroaryl and the 5- to 6-membered heteroaryl contains 1 or 2 identical or different heteroatoms selected from N or O, and any of the phenyl, the 6-membered heteroaryl, and the 5- to 6-membered heteroaryl is unsubstituted or substituted with 1 or 2 identical or different substituents selected from the group consisting of halogen, cyano, C1-C4-alkyl, and C3-C6-cycloalkyl.

[0099] In one embodiment of the present invention, the compound of formula (I) is 1 is methyl and R 3 , R 5 , R 6 is hydrogen and B 1 is CR10 may be a compound of formula (IA) [ka] (In the formula, R 2 , R 4 , R 7 , R 8 , R 9 , R 10 , R 11 , B 2 , W and Z 1 is as defined for the compounds of formula (I) according to the invention).

[0100] Preferably, in the compound of formula (IA), B 2 is N; and R 2 , R 4 , R 7 , R 8 , R 9 , R 10 , W and Z 1 is as defined for the compounds of formula (I) according to the invention.

[0101] Preferably, in the compound of formula (IA), B 2 is CR 11 and R 2 , R 4 , R 7 , R 8 , R 9 , R 10 , R 11 , W and Z 1 is as defined for the compounds of formula (I) according to the invention.

[0102] Preferably, in the compound of formula (IA), W is O, N, —CH2O— # , *-CH2NH- # , *-CH2S- # or a bond, where the star (*) indicates the position of the link to the carbonyl group, and # indicates Z 1 and R 2 , R 4 , R 7 , R8 , R 9 , R 10 , R 11 , B 2 and Z 1 is as defined for the compounds of formula (I) according to the invention.

[0103] Preferably, in the compound of formula (IA), W is O, N, —CH2O— # , *-CH2NH- # , *-CH2S- # , or *-CH2- # where the star (*) indicates the position of the link to the carbonyl group, and # indicates Z 1 and R 2 , R 4 , R 7 , R 8 , R 9 , R 10 , R 11 , B 2 and Z 1 is as defined for the compounds of formula (I) according to the invention.

[0104] Preferably, in the compound of formula (IA), W is O, N, —CH2O— # , *-CH2NH- # , or *-CH2S- # or a bond, where the star (*) indicates the position of the link to the carbonyl group, and # indicates Z 1 Indicates the position where it is connected to Z 1is selected from C1-C6-alkyl, phenyl, or 5- to 6-membered heteroaryl; the C1-C6-alkyl is unsubstituted or substituted with 1, 2, or 3 identical or different substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, phenyl, 5- to 6-membered heteroaryl, and C3-C6-cycloalkyl, and the 5- to 6-membered heteroaryl contains 1 or 2 heteroatoms selected from N or O, and either of the phenyls and either of the 5- to 6-membered heteroaryls is unsubstituted or substituted with 1 or 2 identical or different substituents selected from the group consisting of halogen, cyano, C1-C4-alkyl, and C3-C6-cycloalkyl; and R 2 , R 4 , R 7 , R 8 , R 9 , R 10 , R 11 and B 2 is as defined for the compounds of formula (I) according to the invention.

[0105] Preferably, in the compound of formula (IA), W is O, N, —CH2O— # , *-CH2NH- # , or *-CH2S- # or a bond, where the star (*) indicates the position of the link to the carbonyl group, and # indicates Z 1 Indicates the position where it is connected to Z 1is selected from C1-C6-alkyl, phenyl, or 6-membered heteroaryl; wherein the C1-C6-alkyl is unsubstituted or substituted with 1, 2, or 3 identical or different substituents selected from the group consisting of halogen, C1-C4-alkyl, C1-C4-haloalkyl, phenyl, 5- to 6-membered heteroaryl, and C3-C6-cycloalkyl; wherein any of the 6-membered heteroaryl and the 5- to 6-membered heteroaryl contains 1 or 2 identical or different heteroatoms selected from N or O, and any of the phenyl, the 6-membered heteroaryl, and the 5- to 6-membered heteroaryl is unsubstituted or substituted with 1 or 2 identical or different substituents selected from the group consisting of halogen, cyano, C1-C4-alkyl, and C3-C6-cycloalkyl; and R 2 , R 4 , R 7 , R 8 , R 9 , R 10 , R 11 and B 2 is as defined for the compounds of formula (I) according to the invention.

[0106] Preferably, in the compound of formula (IA), R 2 is hydrogen, chlorine, or methyl; R 4 is hydrogen or methyl; R 7 is hydrogen, C1-C4 alkyl, or C3-C6-cycloalkyl; R 8 is hydrogen, bromine, chlorine, or cyano; R 9 is hydrogen, bromine, chlorine, cyano, methyl, or methoxy; R 10 is hydrogen, bromine, chlorine, or cyano; B 2 is N; and W and Z 1 is as defined for the compounds of formula (I) according to the invention.

[0107] Preferably, in the compound of formula (IA), R 2 is hydrogen, chlorine, or methyl; R 4 is hydrogen or methyl; R 7 is hydrogen, C1-C4 alkyl, or C3-C6-cycloalkyl; R 8 is hydrogen, bromine, chlorine, or cyano; R 9 is hydrogen, bromine, chlorine, cyano, methyl, or methoxy; R 10 is hydrogen, bromine, chlorine, or cyano; B 2 is CR 11 (In the formula, R 11 is hydrogen, bromine, chlorine, or cyano); and W and Z 1 is as defined for the compounds of formula (I) according to the invention.

[0108] Preferably, in the compound of formula (IA), R 2 is hydrogen, chlorine, or methyl; R 4 is hydrogen or methyl; R 7 is hydrogen, C1-C4 alkyl, or C3-C6-cycloalkyl; R 8 is hydrogen, bromine, chlorine, or cyano; R 9 is hydrogen, bromine, chlorine, cyano, methyl, or methoxy; R 10 is hydrogen, bromine, chlorine, or cyano; B 2 is CR 11 (In the formula, R 11 is hydrogen, bromine, chlorine, or cyano); and W is O, N, *-CH2O- # , *-CH2NH- # , *-CH2S-# or a bond, where the star (*) indicates the position of the link to the carbonyl group, and # indicates Z 1 indicates the position of connection to; and Z 1 is C1-C6 alkyl, phenyl, or 5- to 6-membered heteroaryl; said C1-C6 alkyl is unsubstituted or substituted with 1, 2, or 3 identical or different substituents selected from the group consisting of halogen, C1-C4 alkyl, C1-C4 haloalkyl, phenyl, 5- to 6-membered heteroaryl, and C3-C6-cycloalkyl; any of said 5- to 6-membered heteroaryls contains 1 or 2 identical or different heteroatoms selected from N or O; any of said phenyls and any of said 5- to 6-membered heteroaryls is unsubstituted or substituted with 1 or 2 identical or different substituents selected from the group consisting of halogen, cyano, C1-C4 alkyl, and C3-C6-cycloalkyl.

[0109] Preferably, in the compound of formula (IA), R 2 is hydrogen, chlorine, or methyl; R 4 is hydrogen or methyl; R 7 is hydrogen, C1-C4 alkyl, or C3-C6-cycloalkyl; R 8 is hydrogen, bromine, chlorine, or cyano; R 9 is hydrogen, bromine, chlorine, cyano, methyl, or methoxy; R 10 is hydrogen, bromine, chlorine, or cyano; B 2 is CR 11 (In the formula, R 11 is hydrogen, bromine, chlorine, or cyano); and W is O, N, *-CH2O- # , *-CH2NH- # , *-CH2S- #or a bond, where the star (*) indicates the position of the link to the carbonyl group, and # indicates Z 1 indicates the position of connection to; and Z 1 is C1-C6 alkyl, phenyl, or 6-membered heteroaryl; the C1-C6 alkyl is unsubstituted or substituted with 1, 2, or 3 identical or different substituents selected from the group consisting of halogen, C1-C4 alkyl, C1-C4 haloalkyl, phenyl, 5- to 6-membered heteroaryl, and C3-C6 cycloalkyl; any of the 6-membered heteroaryl and 5- to 6-membered heteroaryl contains 1 or 2 identical or different heteroatoms selected from N or O; any of the phenyl, the 6-membered heteroaryl, and the 5- to 6-membered heteroaryl is unsubstituted or substituted with 1 or 2 identical or different substituents selected from the group consisting of halogen, cyano, C1-C4 alkyl, and C3-C6 cycloalkyl.

[0110] Preferably, in the compound of formula (IA), R 2 is hydrogen, chlorine, or methyl; R 4 is hydrogen or methyl; R 7 is hydrogen, C1-C4 alkyl, or C3-C6-cycloalkyl; R 8 is hydrogen, bromine, chlorine, or cyano; R 9 is hydrogen, bromine, chlorine, cyano, methyl, or methoxy; R 10 is hydrogen, bromine, chlorine, or cyano; B 2 is CR 11 (In the formula, R 11 is hydrogen, bromine, chlorine, or cyano); and W is O, N, or a bond; and Z 1 is as defined for the compounds of formula (I) according to the invention.

[0111] Preferably, in the compound of formula (IA), R 2 is hydrogen, chlorine, or methyl; R 4 is hydrogen or methyl; R 7 is hydrogen, C1-C4 alkyl, or C3-C6-cycloalkyl; R 8 is hydrogen, bromine, chlorine, or cyano; R 9 is hydrogen, bromine, chlorine, cyano, methyl, or methoxy; R 10 is hydrogen, bromine, chlorine, or cyano; B 2 is CR 11 (In the formula, R 11 is hydrogen, bromine, chlorine, or cyano); and W is O, N, or a bond; and Z 1 is C1-C6 alkyl, phenyl, or 5- to 6-membered heteroaryl; said C1-C6 alkyl is unsubstituted or substituted with 1, 2, or 3 identical or different substituents selected from the group consisting of halogen, C1-C4 alkyl, C1-C4 haloalkyl, phenyl, 5- to 6-membered heteroaryl, and C3-C6-cycloalkyl; any of said 5- to 6-membered heteroaryls contains 1 or 2 identical or different heteroatoms selected from N or O; any of said phenyls and any of said 5- to 6-membered heteroaryls is unsubstituted or substituted with 1 or 2 identical or different substituents selected from the group consisting of halogen, cyano, C1-C4 alkyl, and C3-C6-cycloalkyl.

[0112] Preferably, in the compound of formula (IA), R 2 is hydrogen, chlorine, or methyl; R 4 is hydrogen or methyl; R 7is hydrogen, C1-C4 alkyl, or C3-C6-cycloalkyl; R 8 is hydrogen, bromine, chlorine, or cyano; R 9 is hydrogen, bromine, chlorine, cyano, methyl, or methoxy; R 10 is hydrogen, bromine, chlorine, or cyano; B 2 is CR 11 (In the formula, R 11 is hydrogen, bromine, chlorine, or cyano); and W is O, N, or a bond; and Z 1 is C1-C6 alkyl, phenyl, or 6-membered heteroaryl; the C1-C6 alkyl is unsubstituted or substituted with 1, 2, or 3 identical or different substituents selected from the group consisting of halogen, C1-C4 alkyl, C1-C4 haloalkyl, phenyl, 5- to 6-membered heteroaryl, and C3-C6 cycloalkyl; any of the 6-membered heteroaryl and 5- to 6-membered heteroaryl contains 1 or 2 identical or different heteroatoms selected from N or O; any of the phenyl, the 6-membered heteroaryl, and the 5- to 6-membered heteroaryl is unsubstituted or substituted with 1 or 2 identical or different substituents selected from the group consisting of halogen, cyano, C1-C4 alkyl, and C3-C6 cycloalkyl.

[0113] In one embodiment of the present invention, the compound of formula (IA) is 2 is CR 11 and compounds of formula (I-A1) wherein W is a bond. [ka] (In the formula, R 2 , R 4 , R 7 , R 8 , R 9 , R 10 , R 11 , W and Z 1is as defined for the compounds of formula (I) according to the invention).

[0114] Preferably, in the compound of formula (I-A1), R 2 is hydrogen, chlorine, or methyl; R 4 is hydrogen or methyl; R 7 is hydrogen, C1-C4 alkyl, or C3-C6-cycloalkyl; R 8 is hydrogen, bromine, chlorine, or cyano; R 9 is hydrogen, bromine, chlorine, cyano, methyl, or methoxy; R 10 is hydrogen, bromine, chlorine, or cyano; R 11 is hydrogen, bromine, chlorine, or cyano; and Z 1 is as defined for the compounds of formula (I) according to the invention.

[0115] Preferably, in the compound of formula (I-A1), R 2 is hydrogen, chlorine, or methyl; R 4 is hydrogen or methyl; R 7 is hydrogen, C1-C4 alkyl, or C3-C6-cycloalkyl; R 8 is hydrogen, bromine, chlorine, or cyano; R 9 is hydrogen, bromine, chlorine, cyano, methyl, or methoxy; R 10 is hydrogen, bromine, chlorine, or cyano; R 11 is hydrogen, bromine, chlorine, or cyano; and Z 1is selected from C1-C6 alkyl; said C1-C6 alkyl is unsubstituted or substituted with 1, 2 or 3 identical or different substituents selected from the group consisting of halogen, C1-C4 alkyl, C1-C4 haloalkyl, phenyl, 5- to 6-membered heteroaryl, and C3-C6-cycloalkyl; said 5- to 6-membered heteroaryl contains 1 or 2 identical or different heteroatoms selected from N or O; said phenyl and said 5- to 6-membered heteroaryl are unsubstituted or substituted with 1 or 2 identical or different substituents selected from the group consisting of halogen, cyano, C1-C4 alkyl, and C3-C6-cycloalkyl.

[0116] More preferably, in the compound of formula (I-A1), R 2 is hydrogen, chlorine, or methyl; R 4 is hydrogen or methyl; R 7 is hydrogen, C1-C4 alkyl, or C3-C6-cycloalkyl; R 8 is hydrogen, bromine, chlorine, or cyano; R 9 is hydrogen, bromine, chlorine, cyano, methyl, or methoxy; R 10 is hydrogen, bromine, chlorine, or cyano; R 11 is hydrogen, bromine, chlorine, or cyano; and Z 1is selected from C1-C6 alkyl; said C1-C6 alkyl is unsubstituted or substituted with one, two or three identical or different substituents selected from the group consisting of chlorine, fluorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, cyclopropyl, phenyl and 6-membered heteroaryl; said 6-membered heteroaryl contains one heteroatom selected from N, and said phenyl and said 6-membered heteroaryl are unsubstituted or substituted with one or two identical or different substituents selected from the group consisting of chlorine, bromine, fluorine, cyano, methyl, ethyl and cyclopropyl.

[0117] In another embodiment of the present invention, the compound of formula (IA) is 2 is CR 11 and W is O. [ka] (In the formula, R 2 , R 4 , R 7 , R 8 , R 9 , R 10 , R 11 , W and Z 1 is as defined for the compounds of formula (I) according to the invention).

[0118] Preferably, in the compound of formula (I-A2), R 2 is hydrogen, chlorine, or methyl; R 4 is hydrogen or methyl; R 7 is hydrogen, C1-C4 alkyl, or C3-C6-cycloalkyl; R 8 is hydrogen, bromine, chlorine, or cyano; R 9 is hydrogen, bromine, chlorine, cyano, methyl, or methoxy; R 10 is hydrogen, bromine, chlorine, or cyano; R11 is hydrogen, bromine, chlorine, or cyano; and Z 1 is as defined for the compounds of formula (I) according to the invention.

[0119] Preferably, in the compound of formula (I-A2), R 2 is hydrogen, chlorine, or methyl; R 4 is hydrogen or methyl; R 7 is hydrogen, C1-C4 alkyl, or C3-C6-cycloalkyl; R 8 is hydrogen, bromine, chlorine, or cyano; R 9 is hydrogen, bromine, chlorine, cyano, methyl, or methoxy; R 10 is hydrogen, bromine, chlorine, or cyano; R 11 is hydrogen, bromine, chlorine, or cyano; and Z 1 is selected from C1-C6 alkyl, phenyl, or 5- to 6-membered heteroaryl; said C1-C6 alkyl is unsubstituted or substituted with 1, 2, or 3 identical or different substituents selected from the group consisting of halogen, C1-C4 alkyl, C1-C4 haloalkyl, phenyl, 5- to 6-membered heteroaryl, and C3-C6-cycloalkyl; any of said 5- to 6-membered heteroaryl contains 1 or 2 identical or different heteroatoms selected from N or O; any of said phenyls and any of said 5- to 6-membered heteroaryls is unsubstituted or substituted with 1 or 2 identical or different substituents selected from the group consisting of halogen, cyano, C1-C4 alkyl, and C3-C6-cycloalkyl.

[0120] In yet another embodiment of the present invention, the compound of formula (IA) is 2 is CR 11 and compounds of formula (I-A3) where W is N. [ka] (In the formula, R 2 , R 4 , R 7 , R 8 , R 9 , R 10 , R 11 , W and Z 1 is as defined for the compounds of formula (I) according to the invention).

[0121] Preferably, in the compound of formula (I-A3), R 2 is hydrogen, chlorine, or methyl; R 4 is hydrogen or methyl; R 7 is hydrogen, C1-C4 alkyl, or C3-C6-cycloalkyl; R 8 is hydrogen, bromine, chlorine, or cyano; R 9 is hydrogen, bromine, chlorine, cyano, methyl, or methoxy; R 10 is hydrogen, bromine, chlorine, or cyano; R 11 is hydrogen, bromine, chlorine, or cyano; and Z 1 is as defined for the compounds of formula (I) according to the invention.

[0122] Preferably, in the compound of formula (I-A3), R 2 is hydrogen, chlorine, or methyl; R 4 is hydrogen or methyl; R 7 is hydrogen, C1-C4 alkyl, or C3-C6-cycloalkyl; R 8 is hydrogen, bromine, chlorine, or cyano; R 9 is hydrogen, bromine, chlorine, cyano, methyl, or methoxy; R 10 is hydrogen, bromine, chlorine, or cyano; R 11 is hydrogen, bromine, chlorine, or cyano; and Z 1 is C1-C6 alkyl, phenyl, or 5- to 6-membered heteroaryl; the C1-C6 alkyl is unsubstituted or substituted with 1, 2, or 3 identical or different substituents selected from the group consisting of halogen, C1-C4 alkyl, C1-C4 haloalkyl, phenyl, 5- to 6-membered heteroaryl, and C3-C6-cycloalkyl; any of the 5- to 6-membered heteroaryl contains 1 or 2 identical or different heteroatoms selected from N or O; any of the phenyls and any of the 5- to 6-membered heteroaryls is unsubstituted or substituted with 1 or 2 identical or different substituents selected from the group consisting of halogen, cyano, C1-C4 alkyl, and C3-C6-cycloalkyl.

[0123] In a further embodiment of the invention, the compound of formula (IA) is 2 is CR 11 and W is -CH2O- # (In the formula, the star (*) indicates the position of the link to the carbonyl group, and # indicates Z 1 (indicating the position where the compound is linked to [ka] (In the formula, R 2 , R 4 , R 7 , R 8 , R 9 , R 10 , R 11 , W and Z 1 is as defined for the compounds of formula (I) according to the invention).

[0124] Preferably, in the compound of formula (I-A4), R 2 is hydrogen, chlorine, or methyl; R 4 is hydrogen or methyl; R 7 is hydrogen, C1-C4 alkyl, or C3-C6-cycloalkyl; R 8 is hydrogen, bromine, chlorine, or cyano; R 9 is hydrogen, bromine, chlorine, cyano, methyl, or methoxy; R 10 is hydrogen, bromine, chlorine, or cyano; R 11 is hydrogen, bromine, chlorine, or cyano; and Z 1 is as defined for the compounds of formula (I) according to the invention.

[0125] Preferably, in the compound of formula (I-A4), R 2 is hydrogen, chlorine, or methyl; R 4 is hydrogen or methyl; R 7 is hydrogen, C1-C4 alkyl, or C3-C6-cycloalkyl; R 8 is hydrogen, bromine, chlorine, or cyano; R 9 is hydrogen, bromine, chlorine, cyano, methyl, or methoxy; R 10 is hydrogen, bromine, chlorine, or cyano; R 11 is hydrogen, bromine, chlorine, or cyano; and Z 1is selected from C1-C6 alkyl, phenyl, or 5- to 6-membered heteroaryl; said C1-C6 alkyl is unsubstituted or substituted with 1, 2, or 3 identical or different substituents selected from the group consisting of halogen, C1-C4 alkyl, C1-C4 haloalkyl, phenyl, 5- to 6-membered heteroaryl, and C3-C6-cycloalkyl; any of said 5- to 6-membered heteroaryl contains 1 or 2 identical or different heteroatoms selected from N or O; any of said phenyls and any of said 5- to 6-membered heteroaryls is unsubstituted or substituted with 1 or 2 identical or different substituents selected from the group consisting of halogen, cyano, C1-C4 alkyl, and C3-C6-cycloalkyl.

[0126] Preferably, in the compound of formula (I-A4), R 2 is hydrogen, chlorine, or methyl; R 4 is hydrogen or methyl; R 7 is hydrogen, C1-C4 alkyl, or C3-C6-cycloalkyl; R 8 is hydrogen, bromine, chlorine, or cyano; R 9 is hydrogen, bromine, chlorine, cyano, methyl, or methoxy; R 10 is hydrogen, bromine, chlorine, or cyano; R 11 is hydrogen, bromine, chlorine, or cyano; and Z 1 is phenyl or a 5- to 6-membered heteroaryl; said 5- to 6-membered heteroaryl contains 1 or 2 identical or different heteroatoms selected from N or O; said phenyl and said 5- to 6-membered heteroaryl are unsubstituted or substituted with 1 or 2 identical or different substituents selected from the group consisting of halogen, cyano, C1-C4 alkyl and C3-C6-cycloalkyl.

[0127] In a further embodiment of the invention, the compound of formula (IA) is 2 is CR 11 and W is -CH2S- # (In the formula, the star (*) indicates the position of the link to the carbonyl group, and # indicates Z 1 (indicating the position where the compound is linked to [ka] (In the formula, R 2 , R 4 , R 7 , R 8 , R 9 , R 10 , R 11 , W and Z 1 is as defined for the compounds of formula (I) according to the invention).

[0128] Preferably, in the compound of formula (I-A5), R 2 is hydrogen, chlorine, or methyl; R 4 is hydrogen or methyl; R 7 is hydrogen, C1-C4 alkyl, or C3-C6-cycloalkyl; R 8 is hydrogen, bromine, chlorine, or cyano; R 9 is hydrogen, bromine, chlorine, cyano, methyl, or methoxy; R 10 is hydrogen, bromine, chlorine, or cyano; R 11 is hydrogen, bromine, chlorine, or cyano; and Z 1 is as defined for the compounds of formula (I) according to the invention.

[0129] Preferably, in the compound of formula (I-A5), R 2 is hydrogen, chlorine, or methyl; R 4is hydrogen or methyl; R 7 is hydrogen, C1-C4 alkyl, or C3-C6-cycloalkyl; R 8 is hydrogen, bromine, chlorine, or cyano; R 9 is hydrogen, bromine, chlorine, cyano, methyl, or methoxy; R 10 is hydrogen, bromine, chlorine, or cyano; R 11 is hydrogen, bromine, chlorine, or cyano; and Z 1 is selected from C1-C6 alkyl, phenyl, or 5- to 6-membered heteroaryl; said C1-C6 alkyl is unsubstituted or substituted with 1, 2, or 3 identical or different substituents selected from the group consisting of halogen, C1-C4 alkyl, C1-C4 haloalkyl, phenyl, 5- to 6-membered heteroaryl, and C3-C6-cycloalkyl; any of said 5- to 6-membered heteroaryl contains 1 or 2 identical or different heteroatoms selected from N or O; any of said phenyls and any of said 5- to 6-membered heteroaryls is unsubstituted or substituted with 1 or 2 identical or different substituents selected from the group consisting of halogen, cyano, C1-C4 alkyl, and C3-C6-cycloalkyl.

[0130] Preferably, in the compound of formula (I-A5), R 2 is hydrogen, chlorine, or methyl; R 4 is hydrogen or methyl; R 7 is hydrogen, C1-C4 alkyl, or C3-C6-cycloalkyl; R 8 is hydrogen, bromine, chlorine, or cyano; R 9 is hydrogen, bromine, chlorine, cyano, methyl, or methoxy; R 10 is hydrogen, bromine, chlorine, or cyano; R 11 is hydrogen, bromine, chlorine, or cyano; and Z 1 is phenyl or a 5- to 6-membered heteroaryl; said 5- to 6-membered heteroaryl contains 1 or 2 identical or different heteroatoms selected from N or O; said phenyl and said 5- to 6-membered heteroaryl are unsubstituted or substituted with 1 or 2 identical or different substituents selected from the group consisting of halogen, cyano, C1-C4 alkyl and C3-C6-cycloalkyl.

[0131] In a further embodiment of the invention, the compound of formula (IA) is 2 is CR 11 and W is -CH2NH- # (In the formula, the star (*) indicates the position of the link to the carbonyl group, and # indicates Z 1 (indicating the position where the compound is linked to [ka] (In the formula, R 2 , R 4 , R 7 , R 8 , R 9 , R 10 , R 11 , W and Z 1 is as defined for the compounds of formula (I) according to the invention).

[0132] Preferably, in the compound of formula (I-A6), R 2 is hydrogen, chlorine, or methyl; R 4 is hydrogen or methyl; R 7 is hydrogen, C1-C4 alkyl, or C3-C6-cycloalkyl; R 8 is hydrogen, bromine, chlorine, or cyano; R 9 is hydrogen, bromine, chlorine, cyano, methyl, or methoxy; R 10 is hydrogen, bromine, chlorine, or cyano; R 11 is hydrogen, bromine, chlorine, or cyano; and Z 1 is as defined for the compounds of formula (I) according to the invention.

[0133] Preferably, in the compound of formula (I-A6), R 2 is hydrogen, chlorine, or methyl; R 4 is hydrogen or methyl; R 7 is hydrogen, C1-C4 alkyl, or C3-C6-cycloalkyl; R 8 is hydrogen, bromine, chlorine, or cyano; R 9 is hydrogen, bromine, chlorine, cyano, methyl, or methoxy; R 10 is hydrogen, bromine, chlorine, or cyano; R 11 is hydrogen, bromine, chlorine, or cyano; and Z 1 is selected from C1-C6 alkyl, phenyl, or 5- to 6-membered heteroaryl; said C1-C6 alkyl is unsubstituted or substituted with 1, 2, or 3 identical or different substituents selected from the group consisting of halogen, C1-C4 alkyl, C1-C4 haloalkyl, phenyl, 5- to 6-membered heteroaryl, and C3-C6-cycloalkyl; any of said 5- to 6-membered heteroaryl contains 1 or 2 identical or different heteroatoms selected from N or O; any of said phenyls and any of said 5- to 6-membered heteroaryls is unsubstituted or substituted with 1 or 2 identical or different substituents selected from the group consisting of halogen, cyano, C1-C4 alkyl, and C3-C6-cycloalkyl.

[0134] Preferably, in the compound of formula (I-A6), R 2is hydrogen, chlorine, or methyl; R 4 is hydrogen or methyl; R 7 is hydrogen, C1-C4 alkyl, or C3-C6-cycloalkyl; R 8 is hydrogen, bromine, chlorine, or cyano; R 9 is hydrogen, bromine, chlorine, cyano, methyl, or methoxy; R 10 is hydrogen, bromine, chlorine, or cyano; R 11 is hydrogen, bromine, chlorine, or cyano; and Z 1 is phenyl or a 5- to 6-membered heteroaryl; said 5- to 6-membered heteroaryl contains 1 or 2 identical or different heteroatoms selected from N or O; said phenyl and said 5- to 6-membered heteroaryl are unsubstituted or substituted with 1 or 2 identical or different substituents selected from the group consisting of halogen, cyano, C1-C4 alkyl and C3-C6-cycloalkyl.

[0135] The presence of one or more possible asymmetric carbon atoms in any of the compounds selected from the compounds of formula (I), (IA), (I-A1), (I-A2), (I-A3), (I-A4), (I-A5), or (I-A6) according to the present invention, or the compounds listed in Tables B-1 to B-27, or the compounds listed in Table P (below), means that the compounds can exist in chiral isomeric forms, i.e., enantiomeric or diastereomeric forms.

[0136] More preferably, the compound of formula (I) according to the present invention is selected from the compounds listed in any one of Tables B-1 to B-27.

[0137] Even more preferably, the compounds of formula (I) according to the present invention are selected from the compounds listed in Table P (below).

[0138] Even more preferably, the compound of formula (I) according to the invention is 3-(2,4-difluorophenyl)-1-[4-(1-methylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]propan-1-one, 2-cyclohexylethyl 4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinoline-2-carboxylate, 2-cyclopropylethyl 4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinoline-2-carboxylate, 1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]heptan-1-one, 1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]hexan-1-one, 3-(2,4-difluorophenyl)-1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]propan-1-one, 1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]-3-(4-fluorophenyl)propan-1-one, 1-[4-methyl-4-(1-methylpyrazol-4-yl)-1,3-dihydroisoquinolin-2-yl]heptan-1-one, 1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]decan-1-one, 1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]octan-1-one, 1-[rac-(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]heptan-1-one, 2-cyclohexylethyl 4-methyl-4-(1-methylpyrazol-4-yl)-1,3-dihydroisoquinoline-2-carboxylate, 2-(2,4-difluorophenoxy)-1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]ethenone, 2-(2,4-difluorophenyl)sulfanyl-1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]ethenone, 2-[(2,4-difluorophenyl)methoxy]-1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]ethenone, 2-cyclohexylethyl rac-(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylate, 3-cyclopentyl-1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]propan-1-one, 1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]-5-(dithiolan-3-yl)pentan-1-one, 1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]-5-methyl-hexan-1-one, 3-(4-bromophenyl)-1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]propan-1-one, 1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]oct-7-yn-1-one, 3-(4-chlorophenyl)-1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]propan-1-one, 3-(3,4-dichlorophenyl)-1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]propan-1-one, 1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]-6,6-difluoro-hex-5-en-1-one, 2-(4-fluorophenyl)ethyl 4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinoline-2-carboxylate, 6,6-difluoro-1-[rac-(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]hex-5-en-1-one, 6,6-difluoro-1-[rac-(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]hexan-1-one, Pentyl rac-(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylate, 7,7,7-trifluoro-1-[rac-(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]heptan-1-one, 1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]-7,7,7-trifluoro-heptan-1-one, 4-(1,5-dimethylpyrazol-4-yl)-N-pentyl-3,4-dihydro-1H-isoquinoline-2-carboxamide, N-(2-cycloheptylethyl)-4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinoline-2-carboxamide, N-(1,3-benzothiazol-2-yl)-4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinoline-2-carboxamide, N-(5-tert-butylisoxazol-3-yl)-4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinoline-2-carboxamide, N-(5-chloro-6-methyl-2-pyridyl)-4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinoline-2-carboxamide, N-(cyclohexylmethyl)-4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinoline-2-carboxamide, 4-(1,5-dimethylpyrazol-4-yl)-N-(m-tolyl)-3,4-dihydro-1H-isoquinoline-2-carboxamide, N-(3-cyclopentylpropyl)-4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinoline-2-carboxamide, N-(3-cyclopropyl-3-methyl-butyl)-4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinoline-2-carboxamide, N-(4-chlorophenyl)-4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinoline-2-carboxamide, N-(4-cyclopropylphenyl)-4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinoline-2-carboxamide, N-(2-cyclohexylethyl)-4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinoline-2-carboxamide, rac-(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-N-pentyl-3,4-dihydro-1H-isoquinoline-2-carboxamide, rac-(1S,4S)-N-[(2,4-difluorophenyl)methyl]-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinoline-2-carboxamide, 3-(2,4-difluorophenyl)-1-[rac-(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]propan-1-one, 1-[(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]-7,7-difluoro-heptan-1-one, 5-cyclopropyl-1-[(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]pentan-1-one, 5-cyclopropyl-1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]pentan-1-one, 4-(1,5-dimethylpyrazol-4-yl)-N-(5-fluoropentyl)-3,4-dihydro-1H-isoquinoline-2-carboxamide, N-(5,5-difluoropentyl)-4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinoline-2-carboxamide, (1S,4S)—N-(3-cyclopropylpropyl)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinoline-2-carboxamide, (1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-N-(5-fluoropentyl)-1-methyl-3,4-dihydro-1H-isoquinoline-2-carboxamide, (1S,4S)—N-(5,5-difluoropentyl)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinoline-2-carboxamide, 5,5-difluoropentyl 4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinoline-2-carboxylate, or 5-fluoropentyl 4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinoline-2-carboxylate.

[0139] In a preferred embodiment of the invention, the compound of formula (I) according to the invention is 3-(2,4-difluorophenyl)-1-[4-(1-methylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]propan-1-one, 2-cyclohexylethyl 4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinoline-2-carboxylate, 2-cyclopropylethyl 4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinoline-2-carboxylate, 1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]heptan-1-one, 1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]hexan-1-one, 3-(2,4-difluorophenyl)-1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]propan-1-one, 1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]-3-(4-fluorophenyl)propan-1-one, 1-[4-methyl-4-(1-methylpyrazol-4-yl)-1,3-dihydroisoquinolin-2-yl]heptan-1-one, 1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]decan-1-one, 1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]octan-1-one, 1-[rac-(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]heptan-1-one, 2-cyclohexylethyl 4-methyl-4-(1-methylpyrazol-4-yl)-1,3-dihydroisoquinoline-2-carboxylate, 2-(2,4-difluorophenoxy)-1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]ethenone, 2-(2,4-difluorophenyl)sulfanyl-1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]ethenone, 2-[(2,4-difluorophenyl)methoxy]-1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]ethenone, 2-cyclohexylethyl rac-(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylate, 3-cyclopentyl-1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]propan-1-one, 1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]-5-(dithiolan-3-yl)pentan-1-one, 1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]-5-methyl-hexan-1-one, 3-(4-bromophenyl)-1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]propan-1-one, 1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]oct-7-yn-1-one, 3-(4-chlorophenyl)-1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]propan-1-one, 3-(3,4-dichlorophenyl)-1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]propan-1-one, 1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]-6,6-difluoro-hex-5-en-1-one, 2-(4-fluorophenyl)ethyl 4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinoline-2-carboxylate, 6,6-difluoro-1-[rac-(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]hex-5-en-1-one, 6,6-difluoro-1-[rac-(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]hexan-1-one, Pentyl rac-(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylate, 7,7,7-trifluoro-1-[rac-(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]heptan-1-one, 1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]-7,7,7-trifluoro-heptan-1-one, 4-(1,5-dimethylpyrazol-4-yl)-N-pentyl-3,4-dihydro-1H-isoquinoline-2-carboxamide, N-(5-chloro-6-methyl-2-pyridyl)-4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinoline-2-carboxamide, N-(cyclohexylmethyl)-4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinoline-2-carboxamide, 4-(1,5-dimethylpyrazol-4-yl)-N-(m-tolyl)-3,4-dihydro-1H-isoquinoline-2-carboxamide, N-(3-cyclopentylpropyl)-4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinoline-2-carboxamide, N-(3-cyclopropyl-3-methyl-butyl)-4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinoline-2-carboxamide, N-(4-chlorophenyl)-4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinoline-2-carboxamide, N-(4-cyclopropylphenyl)-4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinoline-2-carboxamide, N-(2-cyclohexylethyl)-4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinoline-2-carboxamide, rac-(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-N-pentyl-3,4-dihydro-1H-isoquinoline-2-carboxamide, rac-(1S,4S)-N-[(2,4-difluorophenyl)methyl]-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinoline-2-carboxamide, 3-(2,4-difluorophenyl)-1-[rac-(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]propan-1-one, 1-[(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]-7,7-difluoro-heptan-1-one, 5-cyclopropyl-1-[(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]pentan-1-one, 5-cyclopropyl-1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]pentan-1-one, 4-(1,5-dimethylpyrazol-4-yl)-N-(5-fluoropentyl)-3,4-dihydro-1H-isoquinoline-2-carboxamide, N-(5,5-difluoropentyl)-4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinoline-2-carboxamide, (1S,4S)—N-(3-cyclopropylpropyl)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinoline-2-carboxamide, (1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-N-(5-fluoropentyl)-1-methyl-3,4-dihydro-1H-isoquinoline-2-carboxamide, (1S,4S)—N-(5,5-difluoropentyl)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinoline-2-carboxamide, 5,5-difluoropentyl 4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinoline-2-carboxylate, or 5-fluoropentyl 4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinoline-2-carboxylate.

[0140] Compounds of formula (I) according to the present invention can be made as shown in Schemes 1-20 below, where, unless otherwise specified, the definition of each variable is as defined above for compounds of formula (I).

[0141] In particular, R 4 and R 6 is hydrogen, and R 5 Compounds of formula (I), wherein is hydrogen or methyl, can be made as shown in Schemes 1-7 below, where, unless otherwise specified, the definition of each variable is as defined above for compounds of formula (I).

[0142] In any of the following schemes, the possible presence of one or more asymmetric carbon atoms in the compounds of formula (I) according to the invention means that the compounds can occur in chiral isomeric forms, i.e. in enantiomeric or diastereomeric forms.

[0143] The compound of formula (I) can be prepared by a person skilled in the art according to known methods. More specifically, the compound of formula (I) can be prepared by reacting a compound of formula (III) or a salt thereof (wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , B 1 and B 2 is as defined above for compounds of formula (I)) to a compound of formula (II) 1 and W are as defined for compounds of formula (I). This reaction is shown in Scheme 1. [ka] Scheme 1

[0144] In Scheme 1, a compound of formula (II) (wherein Z 1 is as defined for compounds of formula (I)) can be activated to compounds of formula (Iia) by methods known to those skilled in the art and described, for example, in Tetrahedron 2005, 61(46), 10827-10852. For example, compounds of formula (Iia) (wherein X 0 is halogen) is formed by treating a compound of formula (II) with, for example, oxalyl chloride or thionyl chloride in the presence of a catalytic amount of N,N-dimethylformamide (DMF) in an inert solvent such as dichloromethane (DCM) or tetrahydrofuran (THF) at a temperature between 20°C and 100°C, preferably 25°C. Compounds of formula (Iia) can be converted to compounds of formula (III) (wherein R 1 , R 2 , R3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , B 1 and B 2 is as defined for compounds of formula (I), optionally in the presence of a base such as triethylamine or pyridine, to provide compounds of formula (I). Alternatively, compounds of formula (I) can be prepared by treatment of compounds of formula (II) with dicyclohexylcarbodiimide (DCC), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) or 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate (HATU) in an inert solvent such as pyridine, DMF, acetonitrile, DCM or THF, optionally in the presence of a base such as triethylamine, at a temperature between 30° C. and 180° C. to provide activated compounds of formula (Iia), where X 0 is G as described in Scheme 1a 1 , G 2 , or G 3 Finally, compounds of formula (II) can also be activated by reaction with a coupling reagent such as propanephosphonic anhydride (T3P), as described, for example, in Synthesis 2013, 45, 1569, to give compounds of formula (Iia), where X 0 is G as described in Scheme 1a 4 Further reaction of the compound of formula (III) with an amine (or a salt thereof) provides the compound of formula (I). [ka] Scheme 1a

[0145] Compounds of formula (II) can be converted by ester hydrolysis to compounds of formula (Iib) 1 is as described in formula (I), W is a bond, and R 0is C1-C4 alkyl). Various conditions can be used, for example, aqueous sodium hydroxide or aqueous lithium hydroxide and an organic water-miscible solvent such as THF or dimethoxyethane or methanol or ethanol. Such ester hydrolysis is well known to those skilled in the art. Compounds of formula (Ib) can also be directly converted to compounds of formula (I) by reacting compounds of formula (Ib) with compounds of formula (III) in the presence of trimethylaluminum or trimethylaluminum-DABCO complex in an inert solvent such as toluene or DCM. Such reactions have been reported in the literature (see Tetrahedron Lett. 1977, 4171-4174, Tetrahedron Lett. 2006, 5767-5769, and references cited therein). Compounds of formula (II) and (Ib) are commercially available.

[0146] More preferably, compounds of formula (I), where W is O, S, or NH, i.e., compounds of formula (Ia), (Ib), and (Ic), respectively, are prepared as shown in Scheme 1b. [ka] Scheme 1b

[0147] As shown in Scheme 1b, activated carbonyl compounds of formula (IIId) can be converted to carbonyl compounds of formula Lg, optionally in the presence of a base such as pyridine, triethylamine, etc. 1 COLg 1 or Lg 1 COLg 2 It is prepared from a compound of formula (III) by treating with a compound of formula Lg 1 COLg 1 and Lg 1 (C=O)Lg 2Examples of compounds of formula (IIId) include, but are not limited to, phosgene (COCl), diphosgene (ClCO(CO)Cl), triphosgene (ClCO(CO)OCCl), carbonyldiimidazole (CDI), methyl chloroformate (CHO(C=O)Cl), etc. This allows the activation of activated carbonyl compounds of formula (IIId) (wherein Lg 1 is a leaving group, e.g., halogen, N-imidazole, methoxy, etc., and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , B 1 and B 2 is as defined for compounds of formula (I). Compounds of formula (IIId) can then be optionally converted to compounds of formula Z in the presence of a base in an inert solvent such as Me-THF, toluene, dichloromethane (DCM), etc. 1 -NH2 with an amine to obtain a compound of formula (Ia). Examples of such reactions are well known to those skilled in the art (see, for example, J. Org. Chem., 2014, 79(15), 6913-6938). Compounds of formula (IIId) can be converted to compounds of formula Z under the same conditions as above. 1 Alcohols of formula -OH or formula Z 1 -SH with thiol to give compounds of formula (Ib) and (Ic), respectively. Examples of such reactions in the literature include Angew.Chem.Int.Ed.2012,51(17),4166-4170; Eu.J.Med.Chem.2019,176,187-194; J.Med.Chem.2010,53(5),2010-2037; Japanese Patent No. JP57032260,1982.

[0148] Amine (Z 1 -NH2), alcohol (Z 1 -OH), and thiols (Z 1 -SH) is generally commercially available.

[0149] A compound of formula (III) 4 and R 6 is hydrogen and R 5 is hydrogen or methyl, and R 1 , R 2 , R 3 , R 7 , R 8 , R 9 , B 1 and B 2 is as defined for compounds of formula (I), i.e. compounds of formula (IIIa) can be converted to compounds of formula (Iva) (wherein R 4 and R 6 is hydrogen and R 5 is hydrogen or methyl, and R 1 , R 2 , R 3 , R 7 , R 8 , R 9 , B 1 and B 2 (wherein R is as defined for compounds of formula (I)). Such reactions are well known in the literature, and similar reactions are described, for example, in Deng, Zeping et al., Chinese Patent No. CN103772278 and Synthesis 1979, 4, 281-283. Alternatively, compounds of formula (IIIa) can be prepared from compounds of formula (Iva) by reduction with hydrogen in the presence of a suitable metal catalyst, such as Pd, Ir, or Rh, with a suitable ligand, for example, a diphosphine [1,2-bis(diphenylphosphino)ethane (dppe), 1,3-bis(diphenylphosphino)propane (dppp), or 1,4-bis(diphenylphosphino)butane (dppb)]. A similar reaction has been reported, for example, in React. Kinet. Cat. Lett. 2007, 92, 99-104. This reaction is shown in Scheme 2. [ka] Scheme 2

[0150] As shown in Scheme 3, a compound of formula (IIIb) 4 , R 6 and R 7 is hydrogen and R 5 is hydrogen or methyl, and R 1 , R 2 , R 3 , R 8 , R 9 , B 1 and B 2 is as defined for compounds of formula (I), can be converted to compounds of formula (VI) (wherein X 0 is a leaving group such as a halogen, and R 0 is C1-C6 alkyl) to give a compound of formula (V), 4 , R 6 and R 7 is hydrogen and R 5 is hydrogen or methyl, and R 1 , R 2 , R 3 , R 8 , R 9 , B 1 and B 2 is as defined for compounds of formula (I). Alternatively, compounds of formula (V) can be converted to compounds of formula (R 0 CO)2O(wherein, R 0 is a C1-C6 alkyl) in an inert solvent such as DCM, THF, or 2-methyl-THF, optionally in the presence of a base such as triethylamine or dimethylaminopyridine, at a temperature between 0°C and 60°C. Compounds of formula (V) are then metallated with a base, for example, an alkyl metal base such as tert-butyllithium, and an additive such as N,N,N',N'-tetramethylethylenediamine (TMEDA), in an inert polar solvent such as THF or 2-methyl-THF, at low temperature, for example, -78°C to room temperature. 7 -X 0 an electrophile of formula X 0is as already defined, and R 7 is C1-C4 alkyl, C1-C4 alkylcarbonyl, C1-C4 alkoxycarbonyl, N-methoxy-N-methyl-carbonyl, C1-C4 alkylaminocarbonyl, di(C1-C4 alkylamino)carbonyl, or C3-C6 cycloalkyl, which C3-C6 cycloalkyl may be optionally substituted by 1, 2, or 3 substituents independently selected from halogen, cyano, C1-C4 alkyl, C1-C4 haloalkyl, or C1-C4 alkoxy, to give a compound of formula (Va), wherein R 4 and R 6 is hydrogen and R 5 is hydrogen or methyl, and R 0 is C1-C6 alkyl, and R 1 , R 2 , R 3 , R 7 , R 8 , R 9 , B 1 and B 2 is as defined for compounds of formula (I). This reaction is shown in Scheme 3. [ka] Scheme 3

[0151] Compounds of formula (Va) can be prepared by methods known to those skilled in the art from compounds of formula (IIIa) (wherein R 4 and R 6 is hydrogen and R 5 is hydrogen or methyl, and R 1 , R 2 , R 3 , R 7 , R 8 , R 9 , B 1 and B 2 is as defined for compounds of formula (I). For example, a compound of formula (Va) 0is tert-butyl) can be treated with an organic or inorganic acid such as trifluoroacetic acid or HCl to provide a compound of formula (IIIa). This reaction is shown in Scheme 4. [ka] Scheme 4

[0152] A compound of formula (Iva) 4 and R 6 is hydrogen and R 5 is hydrogen or methyl, and R 1 , R 2 , R 3 , R 7 , R 8 , R 9 , B 1 and B 2 is as defined for compounds of formula (I), can be converted to compounds of formula (VIII), where R 1 , R 2 and R 3 is as defined for compounds of formula (I), and X 0 is a halogen, preferably chlorine, bromine or iodine, with a compound of formula (VII) 5 is hydrogen or methyl, and R 7 , R 8 , R 9 , B 1 and B 2 can be prepared by reacting (as defined for compounds of formula (I)) with (as defined for compounds of formula (I)). This reaction is shown in Scheme 5. [ka] Scheme 5

[0153] The Suzuki-Miyaura cross-coupling reaction of a compound of formula (VIII) with a compound of formula (VII) is well known to those skilled in the art and is typically carried out in the presence of a palladium catalyst such as tetrakis(triphenylphosphine)-palladium(0) or [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane complex, and a base such as sodium carbonate or potassium carbonate, in a solvent such as N,N-dimethylformamide, dioxane, or a dioxane-water mixture, at a temperature between room temperature and 160°C, optionally under microwave heating conditions, and preferably under an inert atmosphere. Such reactions are reviewed, for example, in J. Organomet. Chem. 1999, 576, 147-168. Those skilled in the art will also appreciate that the reaction is reversible, i.e., the reaction of a compound of formula (X) (wherein R 1 , R 2 and R 3 is as defined for compounds of formula (I)) and a compound of formula (IX) 5 is hydrogen or methyl, and R 7 , R 8 , R 9 , B 1 and B 2 is as defined for compounds of formula (I), and X 0 is a halogen, preferably chlorine, bromine or iodine, to give a compound of formula (Iva), 4 and R 6 is hydrogen and R 5 is hydrogen or methyl, and R 1 , R 2 , R 3 , R 7 , R 8 , R 9 , B 1 and B 2 It will be appreciated that the reaction can result in the reaction of the compound of formula (I) (wherein R is as defined for the compound of formula (I)). This reaction is shown in Scheme 6. [ka] Scheme 6

[0154] Further cross-coupling chemistry, i.e., C—H activation, can also be used to give compounds of formula (Iva), where R 4 and R 6 is hydrogen and R 5 is hydrogen or methyl, and R 1 , R 2 , R 3 , R 7 , R 8 , R 9 , B 1 and B 2 is as defined for compounds of formula (I)) can also be used in the preparation of (Scheme 7). [ka] Scheme 7

[0155] As shown in Scheme 7, a compound of formula (IX) 5 is hydrogen or methyl, and R 7 , R 8 , R 9 , B 1 and B 2 is as defined for compounds of formula (I), and X 0 is a halogen, preferably chlorine, bromine or iodine) in the presence of a palladium catalyst, typically palladium acetate Pd(Oac)2, a suitable ligand, for example 1,10-phenanthroline, in the presence of a base such as cesium carbonate or potassium carbonate, in an inert solvent such as chlorobenzene, toluene or xylene, at a temperature between room temperature and 180°C, optionally under microwave heating conditions, preferably under an inert atmosphere, to give a compound of formula (XI) (wherein R 1 , R 2 and R 3 is as defined for compounds of formula (I). Similar reactions have been reported in the literature, for example in Chem. Sci. 2013, 4, 2374-2379.

[0156] Compounds of formula (III) can also be prepared from compounds of formula (XVI) (Scheme 8). [ka] Scheme 8

[0157] As shown in Scheme 8, a compound of formula (III) can be prepared by condensing a compound of formula (XVI), where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , B 1 and B 2 is as defined for compounds of formula (I), and R 01 can be prepared by one skilled in the art by carbamate deprotection of a common carbamate protecting group substituent (which may be a component of a methyl, tert-butyl, allyl, 2,2,2-trichloroethyl, or benzyl group). For example, R 01 When is methyl, the product can be obtained by heating at a temperature between room temperature and 200° C., preferably between 20° C. and the boiling point of the reaction mixture, using a suitable solvent such as DCM and a suitable reagent such as iodotrimethylsilane, as described in, for example, J. Am. Chem. Soc. 1992, 114, 5959. The compound of formula (III) thus obtained is converted to a compound of formula (I) (Scheme 1).

[0158] A compound of formula (XVI) 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , B 1 and B 2 is as defined for compounds of formula (I), and R 01 is as defined above) can be converted into an aldehyde of formula (XV) (including formaldehyde in its various forms) (wherein R7 is as defined for compounds of formula (I)) and a compound of formula (XIV) 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 8 , R 9 , B 1 and B 2 is as defined for compounds of formula (I), and R 01 can be formed by the Pictet-Spengler reaction with (as described above) (Scheme 9). [ka] Scheme 9

[0159] A compound of formula (XIV) 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 8 , R 9 , B 1 and B 2 is as defined for compounds of formula (I), wherein R 01 is as defined above) can be reacted with an amine of formula (XIII) (wherein R is as defined above) in the presence of, optionally, a base such as triethylamine or pyridine in a suitable solvent such as DCM at a temperature between −20° C. and the boiling point of the mixture, as described, for example, in Org. Biomol. Chem. 2016, 14, 6853. 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 8 , R 9 , B 1 and B 2 can be prepared by the reaction between methyl chloroformate and a suitable protecting reagent, such as methyl chloroformate, as defined for compounds of formula (I). This reaction is shown in Scheme 10. [ka] Scheme 10

[0160] A compound of formula (XIII) or a salt thereof (wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 8 , R 9 , B 1 and B 2 is as defined for compounds of formula (I), can be reacted with a nitrile of formula (XII) (wherein R 1 , R 2 , R 3 , R 4 , R 8 , R 9 , B 1 and B 2 can be prepared by one skilled in the art by the reaction between the Grignard reagent R (as defined for compounds of formula (I)) and a suitable nucleophile such as (dimethylsulfide)dihydroboron (BMS). 5 MgBr or R 6 MgBr (wherein, R 5 and R 6 (wherein X is as defined for compounds of formula (I)) may be added sequentially or simultaneously as nucleophiles to compounds of formula (XII) to allow the preparation of more highly substituted amines of formula (XIII). Such Grignard additions to nitriles can be carried out in inert solvents such as diethyl ether, tert-butyl methyl ether, and cyclopentyl methyl ether using Ti(O- i This reaction is carried out in the presence of a Lewis acid such as Pr)4 (see Synlett 2007, (4), 652-654). This reaction is shown in Scheme 11. [ka] Scheme 11

[0161] Alternatively, a compound of formula (XIII) 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 8 , R 9 , B 1 and B 2 is as defined for compounds of formula (I), and R 5 , R 6 is hydrogen), i.e., the compound of formula (XIIIa) can be converted to an unsaturated nitro compound of formula (XIIIb), 1 , R 2 , R 3 , R 4 , R 8 , R 9 , B 1 and B 2 is as defined for compounds of formula (I)) and compounds of formula (VIII) 1 , R 2 and R 3 is as defined for compounds of formula (I), and X 0 is a halogen, preferably iodine), followed by reaction between a compound of formula (XIIIb), 1 , R 2 , R 3 , R 4 , R 8 , R 9 , B 1 and B 2 can be prepared by one skilled in the art by subsequent reduction of 2-(2-(2-(2-(2-(2-(2-(2-(2-(2-(2-(2-(2-(2-(2-(2-(2-(2-(2-(2-(2-(2-(2-(2-(2-(2-(2-(3 ...3-(2-(3-(2-(3-(3-(2-(3-(2-(3-(3-(2-(3-(3-(2-(3-(3-(2-(3-(3-(2-(3-(3-(3-(4-(3-(2-(3-(3-(4-(3-(2-(3-(3-(4-(3-(4-(3-(2-(3-(4-(3-(4-(3-(2-(3-(3-(4-(4-(3-(3-(4-(4-(3-(2-(3-(3-(4-(4-(3-(2-(3-(4-(3-(4-(3-(4-(3-(4-(4-(3-(2-(3-(4-(3- [ka] Scheme 12

[0162] A compound of formula (XII) 1 , R2 , R 3 , R 4 , R 8 , R 9 , B 1 and B 2 is as defined for compounds of formula (I)) can be prepared by one skilled in the art according to known methods. More specifically, compounds of formula (XII) and intermediates thereto can be prepared from compounds of formula (XVII) as shown in Scheme 13. [ka] Scheme 13

[0163] For example, a compound of formula (XII) 1 , R 2 , R 3 , R 8 , R 9 , B 1 and B 2 is as defined for compounds of formula (I), and R 4 is different from hydrogen) can be prepared by the reaction of a compound of formula (XIIa), where R 1 , R 2 , R 3 , R 8 , R 9 , B 1 and B 2 is as defined for compounds of formula (I), followed by deprotonation of a suitable alkylating agent R, such as iodomethane 4 -X(where R 4 is a C1-C4 alkyl and X is a halogen).

[0164] A compound of formula (XIIa) 1 , R 2 , R 3 , R 8 , R 9 , B 1 and B 2(wherein X is as defined for compounds of formula (I)) can be prepared from alcohols of formula (XVII) by treatment with cyanotrimethylsilane (TMSCN) in the presence of a base such as lithium carbonate in a non-polar solvent such as DCM at temperatures between 0° C. and the boiling point of the reaction mixture. Such transformations are well known in the literature under a variety of conditions, for example as described in Org. Lett. 2008, 10, 4570 and references therein. This reaction is shown in Scheme 15.

[0165] A compound of formula (III) 1 is CR 10 and B 2 is CR 11 and R 1a is C1-C4 alkyl, and R 2a is hydrogen, halogen or C1-C4 alkyl, and R 3 is hydrogen and R 4a , R 5a , R 6a , R 7a is hydrogen or C1-C4 alkyl, and R 8 , R 9 , R 10 , and R 11 is as defined for compounds of formula (I), i.e., further synthesis of compounds of formula (IIIc) is described below. [ka]

[0166] The compound of formula (IIIc) can also be prepared by the reaction of a compound of formula (XVIII) [ka] (In the formula, R 1 is C1-C4 alkyl, and R 2 is hydrogen, halogen or C1-C4 alkyl, and R 3 is hydrogen and R 4 is hydrogen or C1-C4 alkyl, and R 5 , R 6 , R7 is hydrogen or C1-C4 alkyl, and R 8 , R 9 , R 10 , and R 11 (wherein X is as defined above) in an inert solvent such as chlorobenzene, nitrobenzene, or the like, at a temperature between 0°C and 180°C, with a strong acid such as sulfuric acid, hydrochloric acid, hydrobromic acid, trifluoroacetic acid, triflic acid, or methanesulfonic acid, or a Lewis acid such as aluminum oxychloride or bismuth(III) triflate, to give compounds of formula (IIIc), which are converted to compounds of formula (I) as described above. Those skilled in the art will appreciate that such cyclization can be carried out in the same manner as in the case of compounds of formula (XIX). [ka] and (R 4 is methyl) a compound of formula (XX) [ka] (The substituent R in these compounds 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , and R 11 It will be appreciated that the reaction can proceed through intermediates such as R (which is as defined for compounds of formula (I)). Depending on the reaction conditions, these intermediates can be isolated and / or further converted directly to compounds of formula (IIIc). The skilled artisan will also appreciate that R 7 It will be appreciated that when is C1-C4 alkyl, a mixture of diastereomeric racemic-(syn-IIIc) and racemic-(anti-IIIc) can be obtained in a controllable ratio such that one isomer is formed preferentially over the other (Scheme 14). [ka] Scheme 14

[0167] Intermediates (XVIII), (XIX) and (XX) are novel and therefore form part of the present invention. Compounds (XVIII), (XIX), and (XX) can be prepared as shown in Scheme 15 below and as described in the experimental section. [ka] Scheme 15

[0168] As shown in Scheme 15, a benzylamine of formula (XXI) is used to alkylate a compound of formula (XXII) in an inert solvent such as DMF in the presence of a base such as EtN. The compound (XXIII) thus obtained can be isolated or directly treated in situ with BOC-anhydride to give a compound of formula (XXIV). The compound of formula (XXIV) can be reduced with a hydride source (e.g., NaBH in MeOH / THF) to give the target molecule (XVIIIb), which can then be cyclized with, for example, camphorsulfonic acid in EtOAc to give a compound of formula (XIXb). Alternatively, the compound of formula (XXIV) can be converted to a Grignard reagent R in an inert ether solvent (e.g., THF). 4 MgBr to give a compound of formula (XVIIIa), which can be cyclized with, for example, camphorsulfonic acid in EtOAc to give a compound of formula (XIXa). In compounds (XIX) and (XVIII), R 1a is C1-C4 alkyl, and R 2a is hydrogen, halogen, or C1-C4 alkyl, and R 4a is hydrogen or C1-C4 alkyl, and R 5a , R 6a , and R 7a is hydrogen or C1-C4 alkyl, and R 8 , R 9 , R 10 , and R 11is as defined for compounds of formula (I).

[0169] A further aspect of this Friedel-Crafts chemistry should also be noted. When chemistry is carried out starting from chiral amines (XXIa), i.e., R 7 When R is C1-C4 alkyl, the stereochemistry is retained in the final compound of formula (I). 7 When is methyl, the following is shown in Scheme 16: [ka] Scheme 16

[0170] Compounds of formula (XVII) can be prepared by methods known to those skilled in the art. Compounds of formula (XXI) and (XXII) can be readily prepared by those skilled in the art or are commercially available.

[0171] An alternative method for preparing compounds of formula (I) involves late-stage functionalization of an apical intermediate, as shown in Schemes 17 and 18. [ka] Scheme 17

[0172] As shown in Scheme 17, compounds of formula (III) can be prepared by methods known to those skilled in the art and described above to give compounds of formula (XXVI), where X 0 is a leaving group, for example, a halogen), to give a compound of formula (IIIe). The compound of formula (IIIe) can then be converted to a compound of formula (IIIe) by acylation with an amine (Z 1 -NH2), alcohol (Z 1 -OH), or thiol (Z 1 -SH) to give compounds of formula (Id), (Ie) and (If), respectively, wherein Z 1 and W are as described in formula (I).3 Such nucleophilic substitution reactions on carbon are well known to those skilled in the art. Examples and conditions are described in the Preparative Examples.

[0173] A further example of such a late stage functional group transformation is shown in Scheme 18. [ka] Scheme 18

[0174] As shown in Scheme 18, the reaction of a compound of formula (III) with a compound of formula (XXVII) 0 is a leaving group such as a halogen, preferably Cl), by methods known to those skilled in the art and already described in Scheme 1. The compound of formula (IIIf) formed, where R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , B 1 and B 2 is as defined for compounds of formula (I)) can be elaborated with a heteroatom or carbon nucleophile. For example, the reaction of a compound of formula (IIId) with a compound of formula Z, optionally in the presence of a base, can be carried out by the following procedure: 1 Treatment with a compound of -NH2 results in a compound of formula (Ig). Examples of such reactions are described, for example, in J.Polym.Sci.Part A:Pol.Chem.2012,50(23),4947-4957. Nucleophilic catalysis is also often beneficial for such Michael addition reactions, as discussed in the use of nitrogen nucleophiles to acrylamide catalyzed by imidazolium chloride (see Molecules 2019,24(23),4224). The compound of formula (III) can be converted to a compound of formula Z. 1 -OH and Z 1Treatment with a compound of -SH gives compounds of formula (Ih) and (Ii), respectively. Such Michael addition reactions of alcohols and thiols are known in the literature, see, for example, Polym. Chem. 2018, 9(38), 4716-4723 (alcohol Michael addition reaction); Org. Biomol. Chem. 2020, 18, 6364-6377 (thiol Michael addition reaction). There are various methods known to those skilled in the art that can be used to carry out the Michael addition reaction of carbon nucleophiles to α,β-unsaturated carbonyl derivatives (resulting in compounds of formula (Ij)). These are reviewed in Tetrahedron Organic Chemistry Series, Conjugate Addition Reactions in Organic Synthesis, Elsevier, 1992, vol. 9, pp. 1-61. The Michael addition of α,β-unsaturated carbonyls is also known for boronic acid derivatives using catalytic systems such as 2.5 mol% [RhCl(C2H4)2]2 / (±)-BINAP (5 mol%) in the presence of K3PO4 base in an inert solvent such as dioxane at temperatures between 50 and 100 °C. Such reactions are also described in the literature, e.g., Adv. Synth. Catal. 2013, 355, 1874-1880.

[0175] Salts of compounds of formula (I) can be prepared in a manner known per se: thus, for example, acid addition salts of compounds of formula (I) can be obtained by treatment with a suitable acid or with a suitable ion exchange reagent, and salts with bases can be obtained by treatment with a suitable base or with a suitable ion exchange reagent.

[0176] Salts of compounds of formula (I) can be converted in a customary manner, for example into the free compounds I (acid addition salts) by treatment with a suitable basic compound or a suitable ion exchange reagent, or into salts with a base, for example by treatment with a suitable acid or a suitable ion exchange reagent.

[0177] Salts of compounds of formula (I) can be converted into other salts (acid addition salts, e.g. other acid addition salts) of compounds of formula (I) in a manner known per se, for example by treating the salt of an inorganic acid, such as hydrochloric acid, with a suitable metal salt of the acid, such as sodium, barium or silver salt (e.g. silver acetate), in a suitable solvent (in which inorganic salts that form, for example, silver chloride, are insoluble and therefore precipitate from the reaction mixture).

[0178] Depending on the procedure or reaction conditions, compounds of formula (I) that have salt-forming properties may be available in the free form or in salt form.

[0179] The compounds of formula (I) and, where appropriate, their tautomers, in each free or salt form, can exist in the form of pure isomers, such as enantiomers and / or diastereomers, or as isomeric mixtures, such as enantiomeric mixtures, e.g. racemates, diastereomeric mixtures, depending on the number, absolute and relative configuration of asymmetric carbon atoms occurring in the molecule and / or depending on the configuration of non-aromatic double bonds occurring in the molecule, in one form of the possible isomers or as mixtures thereof; the invention relates to the pure isomers and also to all possible isomeric mixtures, and is to be understood in this sense above and below, respectively, even if details of the stereochemistry are not specifically stated in each case.

[0180] Diastereomeric or racemic mixtures of compounds of formula (I), in free or salt form, depending on which starting materials and procedures are selected, can be separated in known manner on the basis of the physical chemical differences of the components into pure diastereomers or racemates, for example by fractional crystallization, distillation and / or chromatography.

[0181] Enantiomeric mixtures, such as racemates, which may be obtained in a similar manner can be resolved into their optical antipodes by known methods, for example, by recrystallization from an optically active solvent; by chromatography on a chiral adsorbent, for example, by high-performance liquid chromatography (HPLC) on acetylcellulose using suitable microorganisms; by cleavage with specific immobilized enzymes, in which only one enantiomer is complexed, for example, via the formation of inclusion compounds with chiral crown ethers; or by conversion to diastereomeric salts, for example, by reacting the basic end-product racemate with an optically active acid, such as a carboxylic acid, for example, camphoric acid, tartaric acid, or malic acid, or a sulfonic acid, for example, camphorsulfonic acid, and separating the diastereomeric mixtures thereby obtainable, for example, by fractional crystallization according to their different solubilities, from which the desired enantiomer can be liberated by the action of a suitable agent, for example, a basic agent, to give diastereomeric salts.

[0182] Pure diastereomers or enantiomers can be obtained according to the present invention not only by separating the appropriate isomeric mixture, but also by diastereoselective or enantioselective synthesis, which is a method known in the art, e.g., by carrying out the process according to the present invention using starting materials with the appropriate stereochemistry.

[0183] When the individual components have different biological activities, it may be advantageous to isolate or synthesize the respective more biologically active isomer, e.g., enantiomer or diastereomer, or mixture of isomers, e.g., mixture of enantiomers or diastereomers.

[0184] As an example, compounds with two or more asymmetric carbon atoms may exist in diastereoisomeric forms which can be optionally separated using, for example, supercritical fluid chromatography (SFC) chromatography with a chiral column. Such diastereomers may exhibit different fungicidal activity profiles, but all isomers and diastereomers form part of the present invention.

[0185] The compounds of formula (I) have at least three chiral carbon atoms (three stereocenters, the star (*) indicates the chiral carbon atoms) and therefore at least eight stereoisomers are available. These at least eight stereoisomers consist of four sets of enantiomers. [ka]

[0186] A compound of formula (I) 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , B 1 , B 2 , W and Z 1 is as defined for compounds of formula (I), and R 7 is not hydrogen), the relationship between enantiomers and diastereomers is shown in Scheme 21. [ka] [ka] Scheme 21

[0187] Those skilled in the art will recognize these diastereomers and enantiomers of formula (I) (as shown in Scheme 21) (wherein R 1 , R 2 , R 3 , R 4 , R5 , R 6 , R 7 , R 8 , R 9 , B 1 , B 2 , W and Z 1 is as defined for formula (I), and R 7 is not hydrogen) are well understood to be within the scope of the present invention.

[0188] A compound of formula (I) 1 is methyl and R 3 , R 4 , R 5 , R 6 is hydrogen, and R 2 , R 7 , R 8 , R 9 , B 1 , B 2 , W and Z 1 is as defined for compounds of formula (I), and R 7 is not hydrogen), the relationship between enantiomers and diastereomers is shown in Scheme 22. [ka] Scheme 22

[0189] In one embodiment, a compound of formula (I), wherein R 1 is methyl and R 3 , R 4 , R 5 , R 6 is hydrogen, and R 2 , R 7 , R 8 , R 9 , B 1 , B 2 , W and Z 1 is as defined for compounds of formula (I), and R 7 is not hydrogen) and the pyrazole moiety of R 7 have a syn-relationship with each other.

[0190] A compound of formula (I) 1 is methyl and R 3 , R 4 , R 5 , R 6 is hydrogen, and R 2 , R 7 , R 8 , R 9 , B 1 , B 2 , W and Z 1 is as defined for compounds of formula (I), and R 7 is not hydrogen) is shown in Scheme 23. [ka] Scheme 23

[0191] Preferably, the compound of formula (I) 1 is methyl and R 3 , R 4 , R 5 , R 6 is hydrogen, and R 2 , R 7 , R 8 , R 9 , B 1 , B 2 , W and Z 1 is as defined for compounds of formula (I), and R 7 is not hydrogen) and the pyrazole moiety of R 7 have a syn-relationship to each other as shown in Scheme 23.

[0192] The compounds of formula (I) and, where appropriate, their tautomers may each be available in free form or in salt form, where appropriate also in the form of hydrates, and / or may include other solvents, such as those that may have been used for the crystallization of compounds present in solid form.

[0193] As stated above, it has now been surprisingly found that the compounds of formula (I) of the present invention have a very advantageous level of biological activity for practical use in protecting plants from diseases caused by fungi.

[0194] The compounds of formula (I) according to the present invention can be used in the agricultural sector and related fields of use, for example, as active ingredients for controlling plant pests or against non-living organisms for the control of damaging microorganisms or organisms potentially harmful to humans.The novel compounds are distinguished by their excellent activity at low application rates, being well tolerated by plants, and being environmentally safe.They have very useful curative, preventive, and systemic properties and can be used to protect a large number of cultivated plants.The compounds of formula (I) can be used to suppress or eradicate pests that appear on plants or plant parts (fruits, flowers, leaves, stems, tubers, roots) of different crops of useful plants, while simultaneously protecting those parts of the plant that grow later, for example, from phytopathogenic microorganisms.

[0195] 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 microorganisms by treating the plants or plant propagation material and / or harvested food crops, wherein an effective amount of a compound of formula (I) according to the invention is applied to the plant, its part or its habitat.

[0196] The compound of formula (I) according to the present invention can also be used as a fungicide. As used herein, the term "fungicide" refers to a compound that controls, modifies, or prevents the growth of fungi. When used, the term "fungicidally effective amount" refers to the amount of such a compound or a combination of such compounds that can produce an effect on the growth of fungi. Controlling or modifying effects include all deviations from natural occurrence, such as killing, delaying, etc., and prevention includes the formation of a barrier or other defense in plants to prevent fungal infection.

[0197] To protect against fungal infections and phytopathogenic fungi occurring in the soil, the compounds of formula (I) according to the present invention may also be used as dressings for treating plant propagation material, such as seeds, such as fruits, tubers, or grains, or plant cuttings. The propagation material can be treated with a composition containing a compound of formula (I) before planting: for example, seeds can be treated with a dressing before sowing. The active compounds of formula (I) can also be applied to seeds (coatings) by impregnating the seeds in a liquid formulation or coating them with a solid formulation. When the propagation material is planted, the composition can also be applied to the planting site, 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 treated in this way.

[0198] Furthermore, the compounds of formula (I) according to the invention can be used to control fungi in relevant fields, for example in the protection of industrial materials, including wood and wood-related industrial products, food storage, hygiene control.

[0199] Additionally, the present invention can be used to protect non-living materials such as timber, wallboard and paint from fungal attack.

[0200] The compounds of formula (I) according to the invention are active, for example, against disease-causing fungi and fungal vectors as well as phytopathogenic bacteria and viruses. Fungi and fungal vectors as well as plant pathogenic bacteria and viruses involved in these diseases are, for example: 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, Botryosphaeria spp. including B. dermatitidis, Blumeria graminis, Bremia lactucae, B. dothidea, and B. obtusa; Botrytis spp. including B. cinerea; Candida spp. including C. albicans, C. glabrata, C. krusei, C. lusitaniae, C. parapsilosis, and C. tropicalis; Cephaloascus fragrans fragrans, Ceratocystis spp., Cercospora spp. including C. arachidicola, Cercosporidium personatum, Cladosporium spp.), Claviceps purpurea, Coccidioides immitis, Cochliobolus spp., Colletotrichum spp. including C. musae, Cryptococcus neoformans, Diaporthe spp., Didymella spp., Drechslera spp., Elsinoe spp., Epidermophyton spp., Erwinia amylovora Erysiphe spp. including E. amylovora, E. cichoracearum, Eutypa lata, F. culmorum, F. graminearum, F. langsethiae, F. moniliforme, F. oxysporum, F. proliferatum, F. subglutinans, F. solani, Fusarium spp. including Gaeumannomyces graminis, Gibberella fujikuroi, fujikuroi, Gloeodes pomigena, Gloeosporium musarum, Glomerella cingulate, Guignardia bidwellii, Gymnosporangium juniperi-virginianae, Helminthosporium spp., Hemileia spp., H. capsulatumHistoplasma spp. including M. capsulatum, Laetisaria fuciformis, Leptographium lindbergi, Leveillula taurica, Lophodermium seditiosum, Microdochium nivale, Microsporum spp., Monilinia spp., Mucor spp., Mycosphaerella spp. including M. graminicola, M. pomi, Oncobasidium theobromaeon theobromaeon, Ophiostoma piceae, Penicillium spp. including Paracoccidioides spp., P. digitatum, P. italicum, Petriellidium spp., Peronosclerospora spp. including P. maydis, P. philippinensis and P. sorghi, Peronosclerospora spp., Peronospora spp., Phaeosphaeria nodorum, Phakopsora pachyrhizi pachyrhizi, Phellinus igniarus, Phialophora spp., Phoma spp., Phomopsis viticola, Phytophthora spp. including P. infestans, P. halstedii, P. viticolaPlasmopara spp. including P. viticola, Pleospora spp., Podosphaera spp. including P. leucotricha, Polymyxa graminis, Polymyxa betae, Pseudocercosporella herpotrichoides, Pseudomonas spp., Pseudoperonospora spp. including P. cubensis and P. humuli, Pseudoperonospora spp. including P. humuli, Pseudoperonospora spp. including P. tracheiphila, Pseudoperonospora spp. including P. cubensis and P. humuli, Pseudoperonospora spp. including P. tracheophila, P. tracheophila, P. tracheiphil ... 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 alitus 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. Trichoderma spp., including T. harzianum, T. pseudokoningii, and T. viride, Trichophyton spp., Typhula spp., Uncinula necator, Urocystis spp., Ustilago spp., Venturia spp., including V. inaequalis, Verticillium spp., and Xanthomonas spp.

[0201] The compounds of formula (I) according to the invention may be used, for example, on turf, ornamental plants such as flowers, shrubs, broad-leaved trees or evergreen trees such as conifers, as well as for trunk injections, pest management, etc.

[0202] Within the scope of the present invention, 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; fiber plants, such as cotton, flax, hemp, jute and sisal; field crops, such as sugar and fodder beet, coffee, hops, mustard, rapeseed (canola), poppy, sugarcane, sunflower, tea and tobacco; fruit trees, such as apple, apricot, avocado, banana, cherry, citrus, nectarine, peach, pear and plum; grasses, such as bermudagrass, bluegrass, bentgrass, centipedegrass, fescue, ryegrass, St. Augustine grass and zoysiagrass. 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, groundnuts, 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, olives and rubber; vegetables such as asparagus, eggplant, broccoli, cabbage, carrots, cucumber, garlic, lettuce, marrow, melon, okra, onion, pepper, potato, pumpkin, rhubarb, spinach and tomato; and perennial and annual crops such as grapes.

[0203] The term "useful plants" should also be understood to include useful plants that have been rendered tolerant to herbicides such as bromoxynil, or to certain classes 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, by conventional methods of breeding (mutagenesis). An example of a crop that has been rendered tolerant to imidazolinones, such as imazamox, by conventional methods of breeding (mutagenesis) is Clearfield® summer rape (canola). Examples of crops that have been rendered tolerant 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®.

[0204] It should be understood that the term "useful plants" also includes useful plants that have been transformed using recombinant DNA techniques so as to be able to synthesize one or more selectively acting toxins, such as those known from toxin-producing bacteria, particularly bacteria of the genus Bacillus.

[0205] Examples of such plants are YieldGard® (a corn variety expressing a CryIA(b) toxin); YieldGard Root-Feeding Nematode® (a corn variety expressing a CryIIIB(b1) toxin); YieldGard Plus® (a corn variety expressing a CryIA(b) and a CryIIIB(b1) toxin); 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); Nature-Gard® Agrisure® GT Advantage (GA21 glyphosate tolerance trait), Agrisure® CB Advantage (Bt11 corn borer (CB) trait), Agrisure® RW (corn root nematode trait), and Protecta®.

[0206] The term "crop plant" should also be understood to include crop plants that have been transformed using recombinant DNA techniques to be able to synthesize one or more selectively acting toxins, such as those known from toxin-producing bacteria, particularly those belonging to the genus Bacillus.

[0207] Toxins that can be expressed by transgenic plants include, for example, insecticidal proteins from Bacillus cereus or Bacillus popilliae; or insecticidal proteins from Bacillus thuringiensis, such as delta-endotoxins, e.g., Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, or Cry9C, or vegetative insecticidal proteins (Vip), e.g., Vip1, Vip2, Vip3, or Vip3A; or insecticidal proteins from bacteria, e.g., Photorhabdus spp. or Xenorhabdus spp., such as Photorhabdus luminescens, Xenorhabdus nematophilus, etc. insecticidal proteins of nematode-symbiotic bacteria such as Azotoxins; 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, ruffin, 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.

[0208] Furthermore, in the context of the present invention, delta-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 understood to be, in particular, hybrid toxins, truncated toxins, and modified toxins. Hybrid toxins are produced recombinantly by combining different domains of these proteins in a new way (see, for example, WO 02 / 15701). For example, 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 2003 / 018810).

[0209] Examples of such toxins or transgenic 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 0 451 878 and WO 03 / 052073.

[0210] Methods for the preparation of such transgenic plants are generally known to those skilled in the art and are described, for example, in the publications mentioned above. 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.

[0211] The toxins contained in the genetically modified 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).

[0212] 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 the Cry1Ab toxin); YieldGard Rootworm® (a corn variety expressing the Cry3Bb1 toxin); YieldGard Plus® (a corn variety expressing the Cry1Ab and Cry3Bb1 toxins); Starlink® (a corn variety expressing the Cry9C toxin); Herculex I® (a corn variety expressing the Cry1Fa2 toxin and the enzyme phosphinothricin N-acetyltransferase (PAT) to achieve tolerance to the herbicide glufosinate ammonium); NuCOTN 33B® (a cotton variety expressing the Cry1Ac toxin); Bollgard I® (a cotton variety expressing the 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-tolerance trait), Agrisure® CB Advantage (Bt11 corn borer (CB) trait), and Protecta®.

[0213] Further examples of such transgenic 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. Genetically engineered maize (Zea mays) resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) through transgenic expression of a truncated Cry1Ab toxin. Bt11 maize also achieves tolerance to the herbicide glufosinate-ammonium through transgenic expression of the enzyme PAT. 2. Bt176 maize, registration number C / FR / 96 / 05 / 10, manufactured by Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France. Genetically engineered maize (Zea mays) resistant to attack by the European corn borer (Ostrinia nubilalis and Sesamia nonagrioides) through transgenic expression of the Cry1Ab toxin. Bt176 maize also achieves tolerance to the herbicide glufosinate-ammonium through transgenic expression of the enzyme PAT. 3. MIR604 maize, registration number C / FR / 96 / 05 / 10, manufactured by Syngenta Seeds SAS, Chemin de l'Hobit 27, F-31 790 St. Sauveur, France. This maize is resistant to insects through 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 transgenic maize plants is described in WO 2003 / 018810. 4. MON863 maize, registration number C / DE / 02 / 9, manufactured by Monsanto Europe SA270-272 Avenue de Tervuren, B-1150 Brussels, Belgium. MON863 expresses the Cry3Bb1 toxin and confers resistance to certain Coleoptera insects. 5. IPC531 cotton, registration number C / ES / 96 / 02, manufactured by Monsanto Europe SA270-272 Avenue de Tervuren, B-1150 Brussels, Belgium. 6. 1507 corn, registration number C / NL / 00 / 10, manufactured by Pioneer Overseas Corporation, Avenue Tedesco, 7 B-1160 Brussels, Belgium. Maize genetically engineered for expression of the protein Cry1F to achieve resistance to certain Lepidoptera insects and for expression of the PAT protein to achieve tolerance to the herbicide glufosinate ammonium. 7. NK603 x MON810 maize, registration number C / GB / 02 / M3 / 03, manufactured by Monsanto Europe SA270-272 Avenue de Tervuren, B 1150 Brussels, Belgium. This conventional hybrid maize variety is a cross between the genetically modified varieties NK603 and MON810. NK603 x MON810 maize transgenicly expresses the CP4 EPSPS protein from Agrobacterium sp. strain CP4, which confers resistance to the Roundup® herbicide (containing glyphosate), and the Cry1Ab toxin from Bacillus thuringiensis subsp. kurstaki, which confers resistance to certain Lepidoptera, including the European corn borer.

[0214] The compounds of formula (I) according to the invention are effective against diseases caused by plant pathogens, in particular Alternaria species on fruits, vegetables and potatoes; Botrytis cinerea on strawberries, tomatoes, sunflowers, pulses, vegetables and grapes; Rhizoctonia solani on potatoes and vegetables; Uncinula necator on grapes; Cladosporium cucumerinum, Didymella bryoniae, Sphaerotheca fuliginea and Glomerella lagenarium on cucurbits; Leveillula taurica on cucurbits and solanaceous crops. taurica; Fusarium spp. in cereals; Leptosphaeria spp. in cereals; and Zymospetoria spp. in cereals.

[0215] As used herein, the term "habitat" means the field in which the plant is growing or in which the seeds of the plant to be cultivated have been sown or will be sown in the soil. It includes the soil, seeds and seedlings, and established vegetation.

[0216] The term "plant" refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, leaves and fruits.

[0217] The term "plant propagation material" is understood to refer to reproductive parts, such as seeds, of plants, and vegetative parts, such as cuttings or tubers, for example potatoes, which can be used for their propagation. Examples include seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes, and parts of plants. Germinated plants and seedlings that are to be transplanted after germination or emergence from the soil may also be mentioned. These seedlings can be protected by a complete or partial immersion treatment before transplanting. Preferably, "plant propagation material" is understood to refer to seeds.

[0218] The compounds of formula (I) according to the present invention can be used in their original form or, preferably, together with adjuvants conventionally used in the field 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, diluted emulsions, wettable powders, soluble powders, dusts, granules, and capsules, for example, in polymeric materials. The application method, such as spraying, atomizing, dusting, scattering, coating, or pouring, as well as the type of composition, can be selected depending on the intended purpose and the current situation. The composition can also contain further adjuvants, such as stabilizers, antifoaming agents, viscosity modifiers, binders, or tackifiers, as well as fertilizers, sources of trace elements, or other ingredients for achieving special effects.

[0219] Suitable carriers and adjuvants, for example those for agricultural applications, can be solid or liquid and are substances useful in formulation technology, such as natural or regenerated inorganic substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers. Such carriers are described, for example, in WO 1997 / 33890.

[0220] Suspension concentrates are aqueous formulations in which finely divided 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 and crystal growth inhibitors. When used, these concentrates are diluted in water and typically applied as a spray to the area to be treated. The amount of active ingredient can range from 0.5% to 95% of the concentrate.

[0221] Wettable powders are in the form of finely divided particles that disperse readily in water or other liquid carriers. The particles contain the active ingredient held in a solid matrix. Typical solid matrices include fuller's earth, kaolin clay, silica, and other readily 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.

[0222] 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 also contain a liquid carrier such as xylene, high-boiling aromatic naphtha, isophorone, and other non-volatile organic solvents. When used, these concentrates are dispersed in water or other liquid and typically applied as a spray to the area to be treated. The amount of active ingredient can range from 0.5% to 95% of the concentrate.

[0223] 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 or vegetable oils such as high-boiling aromatic naphtha, kerosene, and other petroleum fractions; and / or adhesives such as dextrin, glue, or synthetic resins.

[0224] Dusts are free-flowing mixtures of the active ingredient and finely divided solids such as talc, clays, flours and other organic and inorganic solids which act as dispersants and carriers.

[0225] Microcapsules are typically droplets or granules of an 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 to 50 microns in diameter. The encapsulated liquid typically constitutes 50 to 95% of the capsule's weight and may contain 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, retaining the active species in liquid form within the pores of the granule. Granules typically range in diameter from 1 millimeter to 1 centimeter, preferably 1 to 2 millimeters. Granules are formed by extrusion, agglomeration, or prilling, or are naturally occurring. 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 xanthates.

[0226] Other useful formulations for agrochemical applications include simple solutions of the active ingredient in a solvent in which it is completely soluble at the desired concentration, such as acetone, alkylated naphthalenes, xylene, and other organic solvents. Pressurized sprayers can also be used, in which the active ingredient is dispersed in finely divided form as a result of evaporation of the low-boiling dispersant solvent carrier.

[0227] Suitable agricultural adjuvants and carriers useful in formulating compositions of the present invention in the formulation types described above are well known to those skilled in the art.

[0228] Liquid carriers that can be used include, for example, water, toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetate, 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, alkylpyrrolidinone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1,1,1-Trichloroethane, 2-heptanone, α-pinene, d-limonene, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, γ-butyrolactone, glycerol, glycerol diacetate, glycerol monoacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate, isooctane, isophorone, isopropyl benzene, isopropyl myristate, lactic acid, laurylamine, mesityl oxide, methoxypropanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, methylene chloride, m-xylene, n-hexane, n-octyl alcohol Examples of solvents include methyl amine, octadecanoic acid, octylamine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol (PEG 400), 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, ethylene glycol, propylene glycol, glycerin, and N-methyl-2-pyrrolidinone. Water is generally the carrier of choice for dilution of concentrates.

[0229] 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, soy flour, pumice, wood flour, walnut hulls, and lignin.

[0230] A wide variety of surfactants are advantageously employed in both the liquid and solid compositions, especially those designed to be diluted with a carrier before application. These agents, when used, usually constitute from 0.1% to 15% by weight of the formulation. They may be anionic, cationic, nonionic, or polymeric in character and may be used as emulsifying agents, wetting agents, suspending agents, or for other purposes. Typical surfactants include alkyl sulfates such as diethanolammonium lauryl sulfate; alkylaryl sulfonates, for example, calcium dodecylbenzene sulfone sulfate; alkylphenol-alkylene oxide adducts, for example, nonylphenol-C.sub.18 ethoxylate; alcohol-alkylene oxide adducts, for example, tridecyl alcohol-C.sub.16 ethoxylate; soaps, such as sodium stearate; alkylnaphthalene sulfonates, for example, sodium dibutylnaphthalene sulfonate; dialkyl esters of sulfosuccinates, such as sodium di(2-ethylhexyl)sulfosuccinate; sorbitol esters, for example, sorbitol oleate; quaternary amines, such as lauryltrimethylammonium chloride; polyethylene glycol esters of fatty acids, for example, polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono- and dialkyl phosphate esters.

[0231] Other adjuvants commonly used in agricultural compositions include crystallization inhibitors, viscosity modifiers, suspending agents, spray droplet modifiers, pigments, antioxidants, foaming agents, antifoaming agents, light-blocking agents, compatibilizers, defoamers, sequestering agents, neutralizing agents and buffers, corrosion inhibitors, dyes, odorants, spreading agents, penetration aids, micronutrients, emollients, lubricants and adhesives.

[0232] In addition, other biocidal active ingredients or compositions can be combined with the composition of the present invention, used in the method of the present invention, and applied simultaneously or sequentially with the composition of the present invention.When applied simultaneously, these additional active ingredients can be formulated together with the composition of the present invention or mixed, for example, in a spray tank.These additional biocidal active ingredients can be fungicides, herbicides, insecticides, bactericides, acaricides, nematicides and / or plant growth regulators.

[0233] Pesticides are referred to herein using their common names and are known, for example, from “The Pesticide Manual”, 15th Ed., British Crop Protection Council 2009.

[0234] Additionally, the compositions of the present invention can be applied in conjunction 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.

[0235] The compound of formula (I) according to the present invention is usually used in the form of agrochemical compositions, and can be applied to the cropland or the plants to be treated simultaneously or successively with other compounds.These additional compounds can be, for example, fertilizers or sources of trace elements or other preparations that affect 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, and if necessary, also contain additional carriers, surfactants or application-promoting adjuvants that are commonly used in the technical field of formulations.

[0236] The compounds of formula (I) according to the invention may also be used in the form of (fungicidal) compositions for the control against or protection against phytopathogenic microorganisms, containing 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 available salt, and at least one of the adjuvants mentioned above.

[0237] Therefore, the present invention provides a composition, preferably a fungicidal composition, comprising at least one compound of formula (I) according to the present invention, 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 or more pesticide active compounds, for example, additional fungicidal active ingredients.

[0238] The compound of formula (I) according to the invention may be the only active ingredient of the composition or, if 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 effects.

[0239] Examples of suitable additional active ingredients include 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, 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, organophosphate fungicides, organotin fungicides, oxathiin fungicides, oxazole fungicides, phenylsulfamide fungicides, polysulfide fungicides, pyrazole fungicides, pyridine fungicides, pyrimidine fungicides, pyrrole fungicides, quaternary ammonium fungicides, quinoline fungicides, quinone fungicides, quinoxaline 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.

[0240] Examples of suitable additional active ingredients 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, alamite, arsenic trioxide, azobenzene, azotoate, benomyl, benoxafos, benzyl benzoate, bixafen, brofenvalerate. , Bromocyclen, Bromophos, Bromopropylate, Buprofezin, Butocarboxim, Butoxycarboxim, Butylpyridaben, Calcium polysulfide, Camphechlor, Carbanolate, Carbophenothion, Cimiazole, Chimicianat, Chlorbeneside, Chlordimeform, Chlordimeform Hydrochloride, Chlorphenetole, Chlorfenson, Chlorphenesulfide, Chlorbenzilate, Chlormebuform, Chlormethiuron, Chloropropylate, Chlorthiophos, Cinerin I, Cinerin II, Cinerin, Closantel, Coumaphos, Chloro Tamiton, Crotoxyphos, Kufraneb, 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, Dicrifos, Dienochlor, Dimefox, Zinex, Zinex-diclexin, Dinocap-4, Dinocap-6, Dinocton, Dinopenton, Dinosulfone, Dinotervon, Dioxathion, Diphenylsulfone, Disulfiram, DNOC, Do Fenapine, doramectin, endothion, eprinomectin, ethoate-methyl, etrimphos, fenazaflor, fenbutatin oxide, fenothiocarb, fenpyrad, fenpyroximate, fenpyrazamine, fenthone, fentrifanil, flubenzimine, flucycloxuron, fluenethyl, fluorbenside, FMC1137, formetanate, formetanate hydrochloride, formparanate, gamma-HCH, gliodin, halfenprox, hexadecylcyclopropanecarboxylate, isocarbophos, jasmolin I,Jasmolin II, iodofenphos, lindane, malonobene, mecarbam, mefosfolan, 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, nifururidide, nikkomycin, nitrilacarb, nitrilacarb 1:1 zinc chloride complex, omethoate, oxydeprophos, oxydisulfonate Photon, pp'-DDT, parathion, permethrin, fenkapton, phosalone, phospholane, phosphamidon, polychloroterpenes, polynactin, proclonol, promacyl, propoxar, prothidathion, prothoate, pyrethrin I, pyrethrin II, pyrethrins, pyridaphenthion, pirimitate, quinalphos, quinthiofos, R-1492, phosglycine, rotenone, shradan, cebufos, selamectin, sofamid, SSI-121, sulfiram, sulfuramide, sulfotep, sulfur, diflobidazin, tau-fluva Linate, TEPP, Terbam, Tetradifon, Tetrasulf, Thiafanox, Thiocarboxim, Thiofanox, Thiometon, Thioquinox, Thuringiensis, Triamiphos, Triatene, Triazophos, Triazuron, Tripenophos, Trinactin, Vamidothion, Vaniliprole, Bethoxazin, Copper dioctanoate, Copper sulfate, Sibutrin, Dichlorn, Dichlorophen, Endothal, Fentin, Slaked lime, Nabam, Quinoclamine, Quinonamide, Simazine, Triphenyltin acetate, Triphenyltin hydroxide, Crufomate, Pi Perazine, 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, dodisin, fenaminosulf, formaldehyde, hydralgafen, kasugamycin, kasugamycin hydrochloride hydrate, nickel bis(dimethyldithiocarbamate), nitrapyrin, 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, Aphidiolectus colemani, Aphidoletes aphidomiza, Autographa californica NPV, Bacillus sphaericus sphaericus Neide, Beauveria brongniartii, Chrysoperla carnea, Red-spotted ladybird (Cryptolaemus montrouzieri), Codling moth (Cydia pomonella) GV, Leaf-grating wasp (Dacnusa sibirica), Diglyphus isaea, Green house wasp (Encarsia formosa), Desert wasp (Eretmocerus eremicus), Heterorhabditis bacteriophora bacteriophora and H. megidis, ladybug (Hippodamia convergens), Leptomastix dactylopii, Macrolophus caliginosus,Armyworm moth (Mamestra brassicae) NPV, Metaphycus helvolus, Metarhizium anisopliae var. acridum, Metarhizium anisopliae var. anisopliae, pine sawfly (Neodiprion sertifer) NPV and N. lecontei NPV, Orius spp., Paecilomyces fumosoroseus, Phytoseiulus persimilis, Steinernema bibionis, Steinernema carpocapsae, Steinernema feltiae, Steinernema glaseri, Steinernema riobrave, Steinernema riobravis, Steinernema scapterisci, Steinernema spp., Trichogramma spp., Typhlodromus occidentalis occidentalis), Verticillium lecanii, afolate, visadil, busulfan, dimatif, hemel, hempa, metepa, methiotepa, methyl afolate, molzide, penfluron, tepa, thiohempa, thiotepa, trethamine, uredepa, (E)-dec-5-en-1-yl acetate and (E)-dec-5-en-1-ol, (E)-tridec-4-en-1-yl acetate, (E)-6-methylhept-2-en-4-ol, (E,Z)-tetradec-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)-icosa-13-en-10-one, (Z)-tetradec-7-en-1-al, (Z)-tetradec-9-en-1-ol, (Z)-tetradec-9-en-1-yl acetate, (7E,9Z)-dodeca-7,9-dien-1-yl acetate, (9Z,11E)-tetradec-9,11-dien-1-yl acetate, (9Z,12E)-tetradec-9,12-dien-1-yl acetate, 14-methyloctadec-1-ene, 4-methylnonan-5-ol and 4-methylnonan-5-one, alpha-multistriatin, brevicomin, codrelure, codlemone, curua, disparua, dodec-8-en-1-yl acetate, dodec-9-en-1-yl acetate, dodec-8,10-dien-1-yl acetate, dominicalure, ethyl 4-methyloctanoate, eugenol, frontalin, granddure, granddure I, granddure II, granddure III , Grandolure IV, Hexalure, Ipsdienol, Ipsenol, Japonilure, Lineatin, Littlea, Rupulure, Medulure, Megatomoic Acid, Methyleugenol, Muscalure, Octadeca-2,13-dien-1-yl Acetate, Octadeca-3,13-dien-1-yl Acetate, Olfuralure, Orictalure, Ostramon, Siglua, Soldigin, Sulcatol, Tetradec-11-en-1-yl Acetate, Trimedulure, Trimedulure A, Trimedulure B1, Trimedulure B2, Trimedulure C, Trunk-Cole , 2-(octylthio)ethanol, butopyronoxyl, butoxy(polypropylene glycol), dibutyl adipate, dibutyl phthalate, dibutyl succinate, diethyl toluamide, dimethylcarbate, dimethyl phthalate, ethyl hexanediol, hexamide, methoquin-butyl, methyl neodecaneamide, oxamate, picaridin, 1-dichloro-1-nitroethane, 1,1-dichloro-2,2-bis(4-ethylphenyl)ethane, 1,2-dichloropropane and 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 dimethyl carbamate, 2-(2-butoxyethoxy)ethyl thiocyanate, 2-(4,5-dimethyl-1,3-dioxolan-2-yl)phenyl methyl carbamate, 2-(4-chloro-3,5-xylyloxy)ethanol, 2-chlorovinyl diethyl phosphate, 2-imidazolidone, 2-isovalerylindan-1,3-Dione, 2-methyl(prop-2-ynyl)aminophenylmethylcarbamate, 2-thiocyanatoethyl laurate, 3-bromo-1-chloroprop-1-ene, 3-methyl-1-phenylpyrazol-5-yldimethylcarbamate, 4-methyl(prop-2-ynyl)amino-3,5-xylylmethylcarbamate, 5,5-dimethyl-3-oxocyclohex-1-enyldimethylcarbamate, acetione, acrylonitrile, aldrin, allosamidin, allylxycarb, alpha-ecdysone, aluminum phosphide, aminocarb, anabasine, atidathion, azamethiphos, Bacillus thuringiensis delta-endotoxin, barium hexafluorosilicate, barium polysulfide, bartholin, Bayer 22 / 190, Bayer 22408, beta-cyfluthrin, beta-cypermethrin, bioethanomethrin, biopermethrin, bis(2-chloroethyl)ether, borax, bromfenvinphos, bromo-DDT, bufencarb, butacarb, butathiophos, butonate, calcium arsenate, calcium cyanide, carbon disulfide, carbon tetrachloride, cartap hydrochloride, sevadin, chlorbicyclen, chlordane, chlordecone, chloroform, chloropicrin, chlorphoxim, chlorprazophos, cis-resmethrin, cismethrin, clocitrin, copper acetoarsenite, copper arsenate, copper oleate, cumitoate, cryolite, CS 708, cyanofenphos, cyanophos, cyclethrin, cythioate, d-tetramethrin, DAEP, dazomet, decarbofuran, diamidaphos, dikapton, diclofenthion, dicresyl, dicyclanil, dieldrin, diethyl 5-methylpyrazol-3-yl phosphate, dilol, dimefluthrin, dimethane, dimethrin, 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, fensulfothion, fenthion-ethyl, flucofuron, fosmetiran, fospirate, fostietan, furathiocarb, fretrin, guazatine, guazatine acetate, sodium tetrathiocarbonate, halfenprox, HCH, HEOD, heptachlor, heterophos, HHDN, hydrogen cyanide, hikincarb, IPSP, isazophos, isobenzan, isodrin, isofenphos, isolane, isoprothia Oran, isoxathion, juvenile hormone I, juvenile hormone II, juvenile hormone III, kerevan, kinoprene, arsenic lead, leptophos, lilimphos, ritidathion, m-cumenylmethylcarbamate, magnesium phosphide, magidox, mecarfone, menazone, mercurous chloride, mesulfenphos, metam, metam-potassium, metam-sodium, methanesulfonyl fluoride, metoclofos, methoprene, methotrin, methoxychlor, methyl isothiocyanate, methylchloroform, methylene chloride, methoxadiazone, mirex, naphthalophos, na Phthalene, NC-170, nicotine, nicotine sulfate, nithiazine, nornicotine, O-5-dichloro-4-iodophenyl O-ethyl ethylphosphonothioate, 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, para-dichlorobenzene, 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, prothiofos, pyrazophos, pyresmethrin, quassia, quinalphos-methyl, quinothion, lafoxanide, resmethrin, rotenone, kadethrin, ryania, ryanodine, sabadila, shradan, cebufos, SI-0009, tiapronil, sodium arsenite,Sodium cyanide, sodium fluoride, sodium hexafluorosilicate, sodium pentachlorophenoxide, sodium selenate, sodium thiocyanate, sulcofuron, sulcofuron-sodium, sulfuryl fluoride, sulprofos, tar oil, thazimcarb, TDE, tebupirimfos, temephos, telalethrin, tetrachloroethane, cyclofos, thiocyclam, thiocyclam hydrogen oxalate, thionazine, thiosultap, thiosultap-sodium, tralomethrin, transpermethrin, triazamate, trichlormethaphos-3, trichloronat, trimethacarb, tolprocarb, triclopiricarb, triplen, veratridine, veratrine, XMC, zetamethrin, phosphide Zinc, zolaprofos, meperfluthrin, tetramethylfluthrin, bis(tributyltin) oxide, bromoacetamide, ferric phosphate, niclosamido-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, benclotiaz, cytokinin, DCIP, furfural, isamidophos, kinetin, mulberry dark spot fungus (Myrothecium verrucaria) verrucaria) composition, tetrachlorothiophene, xylenol, zeatin, potassium ethylxanthate, acibenzolar, acibenzolar-S-methyl, giant knotweed (Reynoutria sachalinensis) extract, alpha-chlorohydrin, antu, barium carbonate, bisthiosemi, brodifacoum, bromadiolone, bromethalin, chlorophacinone, cholecalciferol, coumachlor, coumafuryl, coumatetralyl, crimidine, difenacoum, difethialone, diphacinone, ergocalciferol, flocoumafen, fluoroacetamide, flupropadiene, flupropadiene hydrochloride, norbormide, fosacetim, phosphorus, pindone, pyrinuron, sciliroside, sodium fluoroacetate,Thallium sulfate, warfarin, 2-(2-butoxyethoxy)ethyl piperonylate, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone, farnesol and nerolidol, berubutin, MGK264, piperonyl butoxide, piprotal, propyl isomers, S421, sesamex, sesamolin, sulfoxide, anthraquinone, copper naphthenate, copper oxychloride, dicyclopentadiene, thiram, zinc naphthenate, ziram, imanin, ribavirin, chlorinconazide, mercuric oxide, thiophanate-methyl, aza Conazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, furametpyr, hexaconazole, imazalil, imibenconazole, ipconazole, metconazole, myclobutanil, paclobutrazol, pefurazoate, penconazole, prothioconazole, pyrifenox, prochloraz, propiconazole, pyrisoxazole, simeconazole, tebuconazole, tetraconazole, trimethoprim, Azimefon, triadimenol, triflumizole, triticonazole, ancymidol, fenarimol, nuarimol, bupirimate, dimethirimol, ethirimol, dodemorph, fenpropidin, fenpropimorph, spiroxamine, tridemorph, cyprodinil, mepanipyrim, pyrimethanil, fenpiclonil, fludioxonil, benalaxyl, furalaxyl, metalaxyl, R-metalaxyl, ofurace, oxadixyl, carbendazim, debacarb, fuberidazole, thiabendazole, chlozolinate, dichlozolin, microzolin , procymidone, vinclozolin, boscalid, carboxin, fenfuram, flutolanil, mepronil, oxycarboxin, penthiopyrad, thifluzamide, dodine, iminoctadine, azoxystrobin, dimoxystrobin, enestrobulin, phenaminestrobin, flufenoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, trifloxystrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, ferbam, mancozeb, maneb,Metiram, propineb, zineb, captafol, captan, fluoroimide, folpet, tolylfluanid, Bordeaux mixture, copper oxide, mancopper, oxine-copper, nitrothar-isopropyl, 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, flusulfamide, fluxapyroxad, fenhexamid, fosetylaluminum, hymexazole, iprovalicarb, cyazofamid, metasulfocarb, metrafenone, pencycuron, phthalide, polyoxin, propamocarb, pyribencarb, proquinazid, pyroquilon, pyriophenone, quinoxyfen, quintozene, tiadinil, triazoxide, tricyclazo ol, triforine, validamycin, valifenalate, zoxamide, mandipropamide, fluveneteram, 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-indan-4-yl]pyridine-3-carboxamide, 4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine-3-carbonitrile, (R)-3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-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-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, fluindapyr, methoxystrobin (jiaxiangjunzhi), rubenmixianan, dichlorbenzizox, mandestrobin, 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-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate, pyraziflumide, impirfluxam, torolprocarb, mefentrifluconazole, ipfentrifluconazole, 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]pyridin 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, ametoctrazine, amisulbrom, penflufen, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-Dimethyl-penta-3-enamide, florylpicoxamide, fenpicoxamide, methallylpicoxamide, tebufloquine, ipflufenoquine, quinofumelin, isofetamide, ethyl 1-[[4-[[2-(trifluoromethyl)-1,3-dioxolan-2-yl]methoxy]phenyl]methyl]pyrazole-3-carboxylate (preparable from the method described in WO 2020 / 056090), ethyl 1-[[4-[(Z)-2-ethoxy-3,3,3-trifluoro -prop-1-enoxy]phenyl]methyl]pyrazole-3-carboxylate (preparable from the method described in WO 2020 / 056090), methyl N-[[4-[1-(4-cyclopropyl-2,6-difluoro-phenyl)pyrazol-4-yl]-2-methyl-phenyl]methyl]carbamate (preparable from the method described in WO 2020 / 097012), methyl N-[[4-[1-(2,6-difluoro-4-isopropyl-phenyl)pyrazole-4 -yl]-2-methyl-phenyl]methyl]carbamate (preparable from the method described in WO 2020 / 097012), 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide (preparable from the method described in WO 2020 / 109391), 6-chloro-N-[2-(2-chloro-4-methyl-phenyl)-2,2-difluoro-ethyl]- 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide (preparable from the method described in WO 2020 / 109391), 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide (preparable from the method described in WO 2020 / 109391), 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, fenamacril, 5-amino-1,3,4-thiadiazole-2-thiol zinc salt (2:1), fluopyram, flufenoxadiaza fluthianil, fluopimomide, pyrapropoin, picarbutrazox, 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, α-(1,1-dimethylethyl)-α-[4'-(trifluoromethoxy)[1,1'-biphenyl]-4-yl]-5-pyrimidinemethanol, fluoxapiprolin, enoxastrobin, methyl(Z)-3-methoxy-2-[2-methyl-5-[4-(trifluoromethyl)triazol-2-yl]phenoxy]propion -2-enoate, methyl (Z)-3-methoxy-2-[2-methyl-5-(4-propyltriazol-2-yl)phenoxy]prop-2-enoate, methyl (Z)-2-[5-(3-isopropylpyrazol-1-yl)-2-methyl-phenoxy]-3-methoxy-prop-2-enoate, methyl (Z)-3-methoxy-2-[2-methyl-5-(3-propylpyrazol-1-yl)phenoxy]prop-2-enoate, Methyl (Z)-3-methoxy-2-[2-methyl-5-[3-(trifluoromethyl)pyrazol-1-yl]phenoxy]prop-2-enoate (these compounds can be prepared by the method described in WO 2020 / 079111), methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate, methyl (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate (these compounds can be prepared by the method described in WO 2020 / 193387). can be prepared), 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, 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, trinexapac, cumoxystrobin, zhongshengmycin, copper thiodiazole, zinc thiazole, amethotractin, iprodione, seboxylamine, 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 from the method described in WO 2015 / 155075); N'-[5-bromo-2-methyl-6-(2- propoxypropoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine (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, 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 from the method 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)oxetan-2-yl]phenyl]-N-methyl-formamidine (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 from 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[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl -isoquinoline (these compounds can be prepared from the method described in WO 2017 / 025510); 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-methylbenzimidazol-1-yl)isoquinoline,

[0033] 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 (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-3-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-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-2-fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile (this compound can be prepared from the method described in WO 2016 / 156290); (4-phenoxyphenyl)methyl 2-amino-6-methyl-pyridine-3-carboxylate (this compound can be prepared from the method described in WO 2014 / 0069 45); 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 by the method described in WO 2011 / 138281); 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-penta-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);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-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);

[0241] The compounds of the present invention may also be used in combination with an antiparasitic agent. Such antiparasitic agents include compounds selected from the macrocyclic lactone class of compounds, such as ivermectin, avermectin, abamectin, emamectin, eprinomectin, doramectin, selamectin, moxidectin, nemadectin, and milbemycin derivatives, as described in EP 0357460, EP 0444964, and EP 0594291. Additional antiparasitic agents include semisynthetic and biosynthetic avermectin / milbemycin derivatives, such as those described in U.S. Pat. No. 5,015,630, WO 9415944, and WO 9522552. Additional antiparasitic agents include benzimidazoles, such as albendazole, cambandazole, fenbendazole, flubendazole, mebendazole, oxfendazole, oxibendazole, parbendazole, and other members of this class. Further anthelmintics include imidazothiazoles and tetrahydropyrimidines, such as tetramisole, levamisole, pyrantel pamoate, oxantel or morantel. Further anthelmintics include flukeicides, such as triclabendazole and clorsulon, and cestoicides, such as praziquantel and epsiprantel.

[0242] The compounds of the present invention may also be used in combination with derivatives and analogues of the paraherquamide / marcfortine class of anthelmintics, and 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. 19,520,936.

[0243] The compounds of the invention may also be used in combination with derivatives and analogues of the general class of dioxomorpholine antiparasitic agents as described in WO 9615121, and also with anthelmintic effective cyclic depsipeptides such as those described in WO 9611945, WO 9319053, WO 9325543, EP 0626375, EP 0382173, WO 9419334, EP 0382173 and EP 0503538.

[0244] 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.

[0245] The compounds of the present invention may also be used in combination with terpene alkaloids, such as those described in WO 95 / 19363 or WO 04 / 72086, particularly the compounds disclosed therein.

[0246] Other examples of such biologically active compounds that may be used in combination with the compounds of the present invention include, but are not limited to: Organophosphates: Acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, bromophos, bromophos-ethyl, cadusafos, chlorethoxyphos, chlorpyrifos, chlorfenvinphos, chlormephos, demeton, demeton-S-methyl, demeton-S-methylsulfone, dialifos, diazinon, dichlorvos, dicrotophos, dimethoate, disulfoton, ethion, ethoprophos, etrimphos, famfur, fenamiphos, fenitrothion, fensulfothion, fenthion, flupyrazophos, fonofos, formothion, fosthiazate, heptenophos, isazophos, isothioate, isoxathion, malathion, methacryl phos, 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, proetamphos, prothiofos, pyraclofos, pyridapenthione, quinalphos, sulprofos, temephos, terbufos, tebupirimphos, tetrachlorvinphos, timeton, triazophos, trichlorfon, vamidothion. 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. Pyrethroids: acrinathrin, allethrin, alphamethrin, (E)-(1R)-cis-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate 5-benzyl-3-furylmethyl, bifenthrin, β-cyfluthrin, cyfluthrin, α-cypermethrin, β-cypermethrin, bioallethrin, bioallethrin ((S)-cyclopentyl isomer), bioresmethrin, bifenthrin, NCI-85193, cycloprothrin, cyhalothrin, cythithrin, cyphenothrin, Deltamethrin, empenthrin, esfenvalerate, etofenprox, fenfluthrin, fenpropathrin, fenvalerate, flucythrinate, flumethrin, fluvalinate (D-isomer), imiprothrin, cyhalothrin, lambda-cyhalothrin, permethrin, fenothrin, prallethrin, pyrethrins (natural products), resmethrin, tetramethrin, transfluthrin, theta-cypermethrin, silafluofen, t-fluvalinate, tefluthrin, tralomethrin, zeta-cypermethrin. 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. Other antiparasitic agents: acequinocyl, amitraz, AKD-1022, ANS-118, azadirachtin, Bacillus thuringiensis, bensultap, bifenazate, binapropacryl, bromopropylate, BTG-504, BTG-505, camfechlor, cartap, chlorobenzilate, chlordimeform, chlorfenapyr, chromafenozide, clothianidin, cyromazine, diaclor, diafenthiuron, DBI-3204, dinactin, dihydroxymethyldihydroxypyrrolidine, dinobuton, dinocap, endosulfan, ethiprole, etofenprox, fenazaquin, flumite, MTI-800, fenpyroximate, fluacrypyrim, flubenzimine, flubrocythrinate, flufenzin, flufenprox, fluproxifen, ha Lofenprox, hydramethylnon, IKI-220, Kanemite, NC-196, Niemgard, Nidinolterfuran, Nitenpyram, SD-35651, WL-108477, pyridalyl, propargite, protrifenbut, pymetrozine, 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, triethoxyspinosyn, trinactin, verbutin, Bertarec, YI-5301. Biological agents: Bacillus thuringiensis subspecies aizawai, kurstaki, Bacillus thuringiensis delta-endotoxin, baculovirus, entomopathogenic bacteria, viruses and fungi. Fungicides: chlortetracycline, oxytetracycline, streptomycin. Other biological agents: enrofloxacin, febantel, penetamate, meloxicam, cephalexin, kanamycin, pimobendan, clenbuterol, omeprazole, tiamulin, benazepril, pyriprole, cefquinome, florfenicol, buserelin, cefovecin, tulathromycin, ceftiowol, carprofen, metaflumizone, prazicalantel, triclabendazole.

[0247] The following mixtures of compounds of formula (I) with active ingredients are preferred: The abbreviation "TX" means one compound selected from the compounds of formula (I), (IA), (I-A1), (I-A2), (I-A3), (I-A4), (I-A5), or (I-A6), or the compounds listed in Tables B-1 to B-27, or the compounds listed in Table P (below), as well as 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 ... -Naphthylacetamide + TX, 4-chlorophenyl phenyl sulfone + TX, acetoprole + TX, aldoxicarb + TX, amidithione + TX, amidothioate + TX, amiton + TX, amiton hydrogen oxalate + TX, amitraz + TX, alamite + TX, arsenic trioxide + TX, azobenzene + TX, azotoate + TX, benomyl + TX, benoxafos + TX, benzyl benzoate + TX, bixafen + TX, brofenvalerate + TX, bromocyclen + TX, bromophos + TX, bromopropylate + TX, buprofen Zin + TX, Butocarboxim + TX, Butoxycarboxim + TX, Butylpyridaben + TX, Calcium polysulfide + TX, Camphechlor + TX, Carbanolate + TX, Carbophenothion + TX, Cimiazol + TX, Chimicianat + TX, Chlorbeside + TX, Chlorfenson + TX, Chlordimeform hydrochloride + TX, Chlorphenetole + TX, Chlorfenson + TX, Chlorphenesulfide + TX, Chlorbenzilate + TX, Chlormebuform + TX, Chlormethuron + TX, Chloropropylate + TX, Chlor Thiophos + TX, Cinerin I + TX, Cinerin II + TX, Cinerin + TX, Closantel + TX, Coumaphos + TX, Crotamiton + TX, Crotoxyphos + TX, Kufraneb + ​​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-methyl sulfone + TX, Dichlofluanid + TX, Dichlorvos + TX,Dicrifos + TX, Dienochlor + TX, Dimefox + TX, Zinex + TX, Zinex-Diclexin + TX, Dinocap-4 + TX, Dinocap-6 + TX, Dinoctone + TX, Dinopentone + TX, Dinosulfone + TX, Dinotervone + TX, Dioxathion + TX, Diphenylsulfone + TX, Disulfiram + TX, DNOC + TX, Dofenapine + TX, Doramectin + TX, Endothion + TX, Eprinomectin + TX, Ethoate-methyl + TX, Etrimfos + TX, Fenazaflor + TX, Fenbutatin Oxide + TX, Fenothione Carb + TX, Fenpyrad + TX, Fenpyroximate + TX, Fenpyrazamine + TX, Fenson + TX, Fentrifanil + TX, Flubenzimin + TX, Flucycloxuron + TX, Fluenethyl + TX, Fluorobenside + TX, FMC1137 + TX, Formetanate + TX, Formetanate Hydrochloride + TX, Formoparanate + TX, Gamma-HCH + TX, Gliodin + TX, Halfenprox + TX, Hexadecylcyclopropanecarboxylate + TX, Isocarbophos + TX, Jasmolin I + TX, Jasmolin II + T X, Iodofenphos + TX, Lindane + TX, Malonoben + TX, Mecarbam + TX, Mefosfolan + 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, Nifluridizide + TX, Nikkomycin + TX, Ni Trilacarb +TX, Nitrilacarb 1:1 zinc chloride complex +TX, Omethoate +TX, Oxydeprophos +TX, Oxydisulfoton +TX, pp'-DDT +TX, Parathion +TX, Permethrin +TX, Fenkapton +TX, Phosalone +TX, Phosphorane +TX, Phosphamidon +TX, Polychloroterpenes +TX, Polynactin +TX, Proclonol +TX, Promacyl +TX, Propoxar +TX, Protidathion +TX, Prothoate +TX, Pyrethrin I +TX, Pyrethrin II +TX, Pyrethrin +TX, Pyridaphenthion +TX,Pirimitate +TX, Quinalphos +TX, Quinthiofos +TX, R-1492 +TX, Phosglycine +TX, Rotenone +TX, Schradan +TX, Cevufos +TX, Selamectin +TX, Sofamid +TX, SSI-121 +TX, Sulfiram +TX, Sulfuramide +TX, Sulfotep +TX, Sulfur +TX, Diflavidazine +TX, Tau-fluvalinate +TX, TEPP +TX, Terbam +TX, Tetradifon +TX, Tetrasulf +TX, Thiafanox +TX, Thiocarboxim +TX, Thiafanox +T X, Thiometon + TX, Thioquinox + TX, Thuringiensis + TX, Triamiphos + TX, Triaten + TX, Triazophos + TX, Triazuron + TX, Tripenophos + 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, Slaked lime + TX, Nabam + TX, Quinoclamine + TX, Quinonamide + TX, Simazine + TX, Acetic acid Triphenyltin + 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-(quinoxaline-2-ylamino)benzenesulfonamide + TX, 8-hydroxyquinoline sulfate + TX, bronopol + TX, copper hydroxide + TX, cresol + TX, dipyrithione + TX, dodisin + TX, fenaminosulf + TX, phoron Mulaldehyde + TX, hydralgafen + TX, kasugamycin + TX, kasugamycin hydrochloride hydrate + TX, nickel bis(dimethyldithiocarbamate) + TX, nitrapyrin + TX, octhilinone + TX, oxolinic acid + TX, oxytetracycline + TX, potassium hydroxyquinoline sulfate + TX, probenazole + TX, streptomycin + TX, streptomycin sesquisulfate + TX, tecloftalam + TX, thiomersal + TX, smaller tea tortrix (Adoxophyes orana) GV + TX,Agrobacterium radiobacter + TX, Amblyseius spp. + 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, Red-spotted ladybird (Cryptolaemus montrouzieri) + TX, Codling moth (Cydia pommelae) + TX, pomonella) GV + TX, leaf-gliding wasp (Dacnusa sibirica) + TX, ichthyophagous wasp (Digliphus isaea) + TX, greenhouse wasp (Encarsia formosa) + TX, desert greenhouse wasp (Eretmocerus eremicus) + TX, Heterorhabditis bacteriophora and H. megidis + TX, ladybug (Hippodamia convergens) + TX, Leptomastix dactylopii dactylopii + TX, Macrolophus caliginosus + TX, Armyworm moth (Mamestra brassicae) NPV + TX, Metaphycus helvolus + TX, Metarhizium anisopliae var. acridum + TX,Metarhizium anisopliae var. anisopliae + TX, pine sawfly (Neodiprions ertifer) NPV and N. lecontei NPV + TX, Orius spp. + TX, Paecilomyces fumosoroseus + TX, Phytoseiulus persimilis + TX, Steinernema bibionis + TX, Steinernema carpocapsae + TX, Steinernema felschiae + TX, 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) + TX, afolate + TX, Visadil + 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 and (E)-dec-5-en-1-ol + TX, (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)-icosa-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)-tetradec-9,11-dien-1-yl acetate +TX, (9Z,12E)-tetradec-9,12-dien-1-yl acetate +TX, 14-methyloctadec-1-ene +TX, 4-methylnonan-5-ol and 4-methylnonan-5-one +TX, alpha-multistriatin +TX, Brevicomin +TX, Codrelure +TX, Codlemone +TX, Curure +TX, Disparlure +TX, Dodec-8-en-1-yl acetate +TX, Dodec-9-en-1-yl acetate +TX, Dodec-8,10-dien-1-yl acetate +TX, Dominicalure +TX, Ethyl 4-methyloctadecyl Noate + TX, Eugenol + TX, Frontalin + TX, Grandolure + TX, Grandolure I + TX, Grandolure II + TX, Grandolure III + TX, Grandolure IV + TX, Hexalure + TX, Ipsdienol + TX, Ipsenol + TX, Japonilure + TX, Lineatin + TX, Littlea + TX, Lupulure + TX, Medulure + TX, Megatomoic acid + TX, Methyleugenol + TX, Muscalure + TX, Octadeca-2,13-dien-1-yl acetate + TX, Octadeca-3,13-dien-1-yl acetate + TX, Ol Furala + TX, Orictala + TX, Ostramon + TX, Siglua + TX, Soldigin + TX, Sulcatol + TX, Tetradec-11-en-1-yl acetate + TX, Trimedula + TX, Trimedula A + TX, Trimedula B1 + TX, Trimedula B2 + TX, Trimedula C + TX, Trunk-Cole + TX, 2-(octylthio)ethanol + TX, Butopyronoxyl + TX, Butoxy(polypropylene glycol) + TX, Dibutyl adipate + TX, Dibutyl phthalate + TX, Dibutyl succinate + TX, Diethyltoluamide + TX,Dimethylcarbate + TX, dimethylphthalate + TX, ethylhexanediol + TX, hexamide + TX, methoquin-butyl + TX, methylneodecanamide + TX, oxamate + TX, picaridin + TX, 1-dichloro-1-nitroethane + TX, 1,1-dichloro-2,2-bis(4-ethylphenyl)ethane + TX, 1,2-dichloropropane and 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 methylphosphate + TX, 2-(1,3-dithiolan-2-yl)furan 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-imidazolidone + 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-xylylmethylcarbamate + TX, 5,5-dimethyl-3-oxocyclohex-1-enyldimethylcarbamate + TX, acetione + TX, acrylonitrile + TX, aldrin + TX, allosamidin + TX, alixycarb + TX, alpha-ecdysone + TX, aluminum phosphide + TX, aminocarb + TX, anabasine + TX, atidathion + TX, azamethiphos + TX, Bacillus thuringiensis delta endotoxin + TX, barium hexafluorosilicate + TX, barium polysulfide + TX, bartholin + TX, Bayer 22 / 190 + TX, Bayer 22408+TX, beta-cyfluthrin+TX, beta-cypermethrin+TX, bioethanomethrin+TX, biopermethrin+TX, bis(2-chloroethyl)ether+TX, borax+TX, bromfenvinphos+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, sevadin+TX, chlorbicyclen+TX, chlordane+TX, chlordecone+TX, chloroform+TX, chloropicrin+TX, chlorphoxim+TX, chlorprazophos+TX, cis-resmethrin+TX, cismethrin+TX, clocitrin+TX, copper acetoarsenite+TX, copper arsenate+TX, Copper oleate +TX, chumithoate +TX, cryolite +TX, CS708 +TX, cyanofenphos +TX, cyanophos +TX, cyclethrin +TX, cythioate +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, dilol +TX, dimefluthrin +TX, dimethane +TX, dimethryn +TX, dimethylvinphos +TX, dimethyllan +TX, dinoprop +TX, dinosam +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+TX, Fenitrothion+TX, Fenoxacrim+TX, Fenpyrithrin+TX, Fensulfothion+TX, Fenthion-ethyl+TX, Flucofuron+TX, Fosmetilan+TX, Fospirate+TX, Fostietan+TX, Furathiocarb+TX, Frethrin+TX, Guazatine+TX, Guazatine acetate+TX, Sodium tetrathiocarbonate+TX, Halfenprox+TX, HCH+TX, HEOD+TX, Heptachlor+TX, Heterofos+TX, HHDN+TX, Hydrogen cyanide+TX, Hikincarb+TX, IPS P+TX, Isazophos+TX, Isobenzan+TX, Isodrin+TX, Isofenphos+TX, Isolane+TX, Isoprothiolane+TX, Isoxathion+TX, Juvenile Hormone I+TX, Juvenile Hormone II+TX, Juvenile Hormone III+TX, Kelevan+TX, Kinoprene+TX, Arsenic Lead+TX, Leptophos+TX, Lilimphos+TX, Ritidathion+TX, m-Cumenylmethylcarbamate+TX, Magnesium Phosphide+TX, Magidox+TX, Mecarfone+TX, Menasone+TX, Mercurous Chloride+TX, Mesulfenphos+TX, Metam+TX, Metam-Potassium+TX, Metam-Sodium+TX, Methanesulfonyl Fluoride+TX, Metoclofos+TX, Methoprene+TX, Methoto Phosphorus + 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-Ethyl 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'-Tetrapropyl Dithiopyrophosphate + TX, Oleic Acid + TX,Para-dichlorobenzene + TX, Parathion-methyl + TX, Pentachlorophenol + TX, Pentachlorophenyl laurate + TX, PH60-38 + TX, Fenkapton + TX, Fosniclor + TX, Phosphine + TX, Phoxim-methyl + TX, Pyrimetaphos + TX, Polychlorodicyclopentadiene isomers + TX, Potassium arsenite + TX, Potassium thiocyanate + TX, Precocene I + TX, Precocene II + TX, Precocene III + TX, Primidophos + TX, Profluthrin + TX, Promecarb + TX, Prothiofos + TX, Pi Lazophos +TX, Pyresmethrin +TX, Quassia +TX, Quinalphos-methyl +TX, Quinothione +TX, Lafoxanide +TX, Resmethrin +TX, Rotenone +TX, Kadetrin +TX, Riania +TX, Ryanodine +TX, Sabadila +TX, Schradan +TX, Cebufos +TX, SI-0009 +TX, Tiapronil +TX, Sodium Arsenite +TX, Sodium Cyanide +TX, Sodium Fluoride +TX, Sodium Hexafluorosilicate +TX, Sodium Pentachlorophenoxide +TX, Sodium Selenite +TX, Sodium Thio Cyanate +TX, Sulkofuron +TX, Sulkofuron-sodium +TX, Sulfuryl Fluoride +TX, Sulprofos +TX, Tar Oil +TX, Thazimcarb +TX, TDE +TX, Tebupirimfos +TX, Temephos +TX, Teralethrin +TX, Tetrachloroethane +TX, Cyclofos +TX, Thiocyclam +TX, Thiocyclam Hydrogen Oxalate +TX, Thionazine +TX, Thiosultap +TX, Thiosultap-sodium +TX, Tralomethrin +TX, Transpermethrin +TX, Triazamate +TX, Trichlormetaphos-3 +TX, Tri Chloronate +TX, trimethacarb +TX, tolprocarb +TX, triclopyricarb +TX, triplenone +TX, veratridine +TX, veratrine +TX, XMC +TX, zetamethrin +TX, zinc phosphide +TX, zolaprofos +TX, meperfluthrin +TX, tetramethylfluthrin +TX, bis(tributyltin) oxide +TX, bromoacetamide +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-isopentanylaminopurine + TX, 2-fluoro-N-(3-methoxyphenyl)-9H-purine-amine plus TX, benclothiaz + TX, cytokinin + TX, DCIP + TX, furfural + TX, isamidophos + TX, kinetin + TX, mulberry dark spot fungus (Myrothecium verrucaria) verrucaria) composition +TX, tetrachlorothiophene +TX, xylenol +TX, zeatin +TX, potassium ethylxanthogenate +TX, acibenzolar +TX, acibenzolar-S-methyl +TX, giant knotweed (Reynoutria sachalinensis) extract +TX, alpha-chlorohydrin +TX, antu +TX, barium carbonate +TX, Bisthiosemi + TX, Brodifacoum + TX, Bromadiolone + TX, Bromethalin + TX, Chlorphacinone + TX, Cholecalciferol + TX, Coumachlor + TX, Coumafuryl + TX, Coumatetralyl + TX, Crimidine + TX, Difenacoum + TX, Difethialone + TX, Diphacinone + TX, Ergocalciferol + TX, Flocoumafen + TX, Fluoroacetamide + TX, Flupropaline + TX, Flupropaline Hydrochloride + TX, Norbormide + TX, Fosacetim + TX, Phosphate + TX, Pindone + TX, Pyrinuron + T X, 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 and nerolidol + TX, berubutin + 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, bromuconazole + TX, cyproconazole + TX, difenoconazole + TX, diniconazole + TX, epoxiconazole + TX, fenbuconazole + TX, fluquinconazole + TX, flusilazole + TX, flutriafol + TX, furametpyr + TX, hexaconazole + TX, imaza ril + TX, imibenconazole + TX, ipconazole + TX, metconazole + TX, myclobutanil + TX, paclobutrazol + TX, pefurazoate + TX, penconazole + TX, prothioconazole + TX, pyrifenox + TX, prochloraz + TX, propiconazole + TX, pyrizoxazole + 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, Fenpropizin + TX, Fenpropimorph + TX, Spiroxamine + TX, Tridemorph + TX, Cyprodinil + TX, Mepanipyrim + TX, Pyrimethanil + TX, Fenpiclonil + TX, Fludioxonil + TX, Benalaxyl + TX, Furalaxyl + TX, Metalaxyl + TX, R-Metalaxyl + TX, Ofurace + TX, Oxadixyl + TX, Carbendazim + TX, Debacarb + TX, Fuberidazole + TX, Thiabendazo ol + TX, chlozolinate + TX, dichlozolin + TX, mycrozolin + TX, procymidone + TX, vinclozolin + TX, boscalid + TX, carboxin + TX, fenfuram + TX, flutolanil + TX, mepronil + TX, oxycarboxin + TX, penthiopyrad + TX, thifluzamide + TX, dodine + TX, iminooctadine + TX, azoxystrobin + TX, dimoxystrobin + TX, enestrobulin + TX, phenaminestrobin + TX, flufenoxystrobin + TX, fluoxastrobin + TX, kresoxim Methyl + TX, Metominostrobin + TX, Trifloxystrobin + TX, Orysastrobin + TX, Picoxystrobin + TX, Pyraclostrobin + TX, Pyrametstrobin + TX, Pyraoxystrobin + TX, Ferbam + TX, Mancozeb + TX, Maneb + ​​TX, Metiram + TX, Propineb + ​​TX, Zineb + ​​TX, Captafol + TX, Captan + TX, Fluorimide + TX, Folpet + TX, Tolylfluanid + TX, Bordeaux mixture + TX, Copper oxide + TX, Mancopper + TX, Oxine-copper + TX, Nitrotar-isoprolol Lopil + TX, Edifenphos + TX, Iprobenfos + TX, Fosdifen + TX, Tolclofos-methyl + TX, Anilazine + TX, Benthiavalicarb + TX, Blasticidin-S + TX, Chloroneb + ​​TX, Chlorothalonil + TX, Cyflufenamid + TX, Cymoxanil + TX, Cyclobutrifluram + TX, Diclocymet + TX, Diclomedine + TX, 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, Metasulfocarb +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, mandipropamide +TX, fluveneteram +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, dipime Titrone + TX, 6-ethyl-5,7-dioxo-pyrrolo[4,5][1,4]dithiino[1,2-c]isothiazole-3-carbonitrile + TX, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide + TX, 4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine-3-carbonitrile + TX, (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, methoxystrobin (jiaxiangjunzhi) + TX, rubenmixianan + TX, diclobenthiazox + 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]propan-2-ol + TX, oxathiapiproline + TX, tert-butyl N-[6-[[[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate + TX, pyraziflumide + TX, impirfluxam + 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-chlorophenyl]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 Bamate + TX, 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine + TX, pyridaclomethyl + 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-trimethyl Tilpyrazol-1-yl)phenoxy]methyl]phenyl]tetrazol-5-one + TX, aminopyrifen + TX, ametoctrazine + TX, amisulbrom + TX, penflufen + TX, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide + TX, flurylpicoxamide + TX, fenpicoxamide + TX, tebufloquin + TX, ipflufenoquin + 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, pyrapropoin + 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-pyridyl]oxy]benzonitrile + TX, Methyltetraprole + TX, α-(1,1-dimethylethyl)-α-[4'-(trimethylindan-4-yl)propyl]benzonitrile + TX Fluoromethoxy)[1,1'-biphenyl]-4-yl]-5-pyrimidinemethanol + TX, fluoxapiprolin + TX, enoxastrobin + TX, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-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 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, cumoxystrobin + TX, zhongshengmycin + TX, copper thiodiazole + TX, zinc thiazole + TX, amethotractin + 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 N'-[5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine + TX (this compound can be prepared by 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 from 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 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-[(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 from 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 can be prepared from 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 by 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]propanamide + 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 azole-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 in 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-phenoxy phenyl)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']dipyrrolo-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]benzoate + TX (this compound can be prepared from the method described in WO 2011 / 138281). Zenecarbothioamide + 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-oxadiazol-3-yl]phenyl]methanone + TX, (3-methylisoxazol-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone + TX 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone + TX (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 + TX (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 + 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 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, flumethylsulfolim + TX, fluoxytioconazole + TX, flufenoxadiazam + TX, methallylpicoxamide + TX;

[0248] A reference in parentheses following an active ingredient, such as [3878-19-1], refers to the Chemical Abstracts Registry Number. The aforementioned mixing partners are publicly 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 listed therein under the entry number shown in parentheses above for the specific compound; for example, the compound "abamectin" is listed under entry number (1). When "[CCN]" is added to a specific compound above, the compound in question is included in the "Compendium of Pesticide Common Names," which is accessible via the Internet at [A. Wood; Compendium of Pesticide Common Names, Copyright 1995-2004]; for example, the compound "acetoprole" is listed at the Internet address http: / / www.alanwood.net / pesticides / acetoprole.html.

[0249] Most of the active ingredients mentioned above are referred to above by so-called "common names", where in each case the relevant "ISO common name" or another "common name" is used. If the name is not a "common name", the nature of the name used instead is given in parentheses for the particular compound. In that case, the IUPAC name, IUPAC / Chemical Abstracts name, "chemical name", "customary name", "compound name" or "development code" is used, or if none of these names and no "common name" is used, an "alternative name" is utilized. "CAS Registry Number" means the Chemical Abstracts Registry Number.

[0250] The active ingredient mixtures of compounds selected from the compounds of formula (I), (IA), (I-A1), (I-A2), (I-A3), (I-A4), (I-A5), or (I-A6), or the compounds listed in Tables B-1 to B-27, or the compounds listed in Table P (below), are preferably mixed in a ratio of 100:1 to 1:100, in particular 50:1 to 1:50, more particularly 20:1 to 1:20, even more particularly 10:1 to 1:10, and even more particularly 5:1 to 1:5, which are by weight.

[0251] The mixture may be used in a method for controlling pests, the method comprising applying a composition comprising the mixture to the pest or its environment, excluding methods for treating the human or animal body by surgery or therapy, or diagnostic methods practiced on the human or animal body.

[0252] Mixtures comprising a compound selected from compounds of formula (IA), (I-A1), (I-A2), (I-A3), (I-A4), (I-A5), or (I-A6), or a compound listed in Tables B-1 to B-27, or a compound selected from compounds listed in Table P (below), and one or more of the above active ingredients can be applied, for example, in a single "ready-mix" form, in combined spray mixtures made up of separate formulations of a single active ingredient such as a "tank mix," and in combined uses of the single active ingredients when applied sequentially, i.e., one after the other over a fairly short period of time, such as a few hours or days. The order of applying the compound selected from the compounds of formula (IA), (I-A1), (I-A2), (I-A3), (I-A4), (I-A5), or (I-A6), or the compounds listed in Tables B-1 to B-27, or the compounds listed in Table P (below), and the active ingredient(s) described above, is not essential to practicing the present invention.

[0253] The compositions according to the invention may also comprise further solid or liquid auxiliaries, such as stabilizers, for example non-epoxidized or epoxidized vegetable oils (for example epoxidized palm oil, rapeseed oil or soybean oil), antifoaming agents, for example silicone oils, preservatives, viscosity regulators, binders and / or tackifiers, fertilizers or other active ingredients for achieving specific effects, for example bactericides, fungicides, nematicides, plant activators, molluscicides or herbicides.

[0254] The compositions according to the invention are prepared in a manner known per se in the absence of auxiliaries, for example by grinding, sieving and / or compressing the solid active ingredient, and in the presence of at least one auxiliary, for example by intimately mixing the active ingredient with one or more auxiliaries and / or grinding. These methods for preparing the compositions and the use of compound (I) for preparing these compositions are also the subject of the present invention.

[0255] Another aspect of the present invention relates to the use of a compound of formula (I) according to the present invention or a preferred individual compound as defined herein, or a composition comprising at least one compound of formula (I) or at least one preferred individual compound as defined herein, or a fungicidal or insecticidal mixture comprising at least one compound of formula (I) or at least one preferred individual compound as defined herein 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.

[0256] A further aspect of the present invention relates to a method for controlling or preventing infestation of plants, such as useful plants, for example crop plants, their propagation material, such as seeds, harvested crops, for example harvested food crops, or non-living material, by phytopathogenic or spoilage microorganisms or organisms, in particular fungal organisms, that are potentially harmful to humans, which method comprises applying a compound of formula (I) according to the present invention or a preferred individual compound as defined herein as active ingredient to the plant, plant parts or its habitat, its propagation material, or any part of the non-living material.

[0257] Control or prevention means reducing damage caused by plant pathogenic microorganisms or organisms, such as insects or especially fungal organisms, or spoilage microorganisms or organisms potentially harmful to humans, to a level that demonstrates improvement.

[0258] Preferred methods for controlling or preventing infestation of crop plants by phytopathogenic microorganisms, particularly fungal organisms, or insects include those in which the compounds of formula (I) according to the present invention and agrochemical compositions containing at least one compound of formula (I) are applied as foliar treatments. The frequency and amount of application depend on the risk of damage by the corresponding pathogen or insect. However, the compounds of formula (I) according to the present invention can also be introduced into the plant through the roots via the soil (systemic action) by irrigating the plant locus with a liquid formulation or by applying the compound to the soil in solid form, for example, in granular form (soil application). In rice crops, such granules can be applied to flooded rice fields. The compounds of formula (I) can also be applied to seeds (coating) by impregnating the seeds or tubers with a liquid formulation of the fungicide or coating them with a solid formulation.

[0259] Formulations, e.g. compositions, containing a compound of formula (I) according to the invention and, if desired, a solid or liquid auxiliary or a monomer encapsulating the compound of formula (I), may typically be prepared in known manner by intimately mixing and / or grinding the compound with an extender, e.g., a solvent, a solid carrier, and, optionally, a surface-active compound (surfactant).

[0260] Advantageous application is usually from 5g to 2kg of active ingredient (ai) per hectare (ha), preferably from 10g to 1kg ai / ha, most preferably from 20g to 600g ai / ha. When used as a seed drench, a convenient dosage is from 10mg to 1g of active substance per kg of seed.

[0261] As used herein, the term "g ai / ha" refers to the application rate expressed in grams [g] of active ingredient [ai] per unit surface [ha]. The unit hectare (symbol ha) is an area of ​​1.00m square meters (1hm 2 ) square or 10,000 square meters. The hectare is a commonly used unit of area in the metric system.

[0262] When the combinations of the invention are used for seed treatment, an amount of 0.001 to 50 g of compound of formula (I) per kg of seed, preferably 0.01 to 10 g per kg of seed, will generally be sufficient.

[0263] Preferably, the compositions comprising compounds of formula (I) according to the present invention are applied either prophylactically (meaning before the onset of the disease) or therapeutically (meaning after the onset of the disease).

[0264] The compositions of the present invention may be in any conventional form, such as a two-part system, dry seed treatment powder (DS), seed treatment emulsion (ES), seed treatment flowable concentrate (FS), seed treatment solution (LS), seed treatment water dispersible powder (WS), seed treatment capsule suspension (CF), seed treatment gel (GF), emulsion concentrate (EC), suspension concentrate (SC), suspoemulsion (SE), capsule suspension (CS), water dispersible granules (WG), emulsifiable granules, etc. They may be employed in the form of granules (EG), emulsions, water-in-oil (EO), emulsions, oil-in-water (EW), microemulsions (ME), oil dispersions (OD), oil-miscible flowables (OF), oil-miscible liquids (OL), soluble concentrates (SL), ultra-low volume suspensions (SU), ultra-low volume liquids (UL), technical concentrates (TK), dispersible concentrates (DC), wettable powders (WP) or any technically feasible formulation in combination with agriculturally acceptable adjuvants.

[0265] Such compositions can be prepared in a conventional manner, for example, by mixing the active ingredient with suitable formulation inerts (diluents, solvents, fillers, and optionally other formulation ingredients such as surfactants, biocides, antifreeze agents, spreading agents, thickeners, and compounds providing auxiliary effects). Conventional sustained-release formulations can also be employed when long-lasting effectiveness 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, can contain surfactants, such as wetting agents and dispersants, as well as other compounds providing auxiliary effects, such as condensation products of formaldehyde with naphthalenesulfonates, alkylarylsulfonates, ligninsulfonates, fatty alkyl sulfates, and ethoxylated alkylphenols and ethoxylated fatty alcohols.

[0266] The seed dressing formulation is applied to seeds in a manner known per se, using the combination of the present invention and a diluent in a suitable seed dressing formulation form, such as an aqueous suspension or a dry powder form with good adhesion to the seeds. 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 slow-release capsules or microcapsules.

[0267] Generally, the formulations contain 0.01 to 90% by weight of active agent, 0 to 20% of an agriculturally acceptable surfactant, and 10 to 99.99% of a solid or liquid inert compound and adjuvant, where the active agent is composed of at least a compound of formula (I) according to the present invention, optionally together with other active agents, particularly microbicides, preservatives, etc. Concentrate forms of the composition generally contain about 2 to 80% by weight, preferably about 5 to 70% by weight, of the active agent. Application forms of the formulations can contain, for example, 0.01 to 20% by weight, preferably 0.01 to 5% by weight, of the active agent. Commercially available products will preferably be formulated as concentrates, but end users will usually use diluted formulations.

[0268] Commercially available products are preferably formulated as concentrates, although end users will typically utilize diluted formulations.

[0269] The application rates vary within wide limits and depend on the nature of the soil, the method of application, the crop plant, the pests to be controlled, the prevailing weather conditions and other factors which depend on the method, time of application and target crop. As a general guideline, the compounds may be applied at a rate of 1 to 2000 l / ha, especially 10 to 1000 l / ha.

[0270] A preferred formulation may have the following composition (by weight): Emulsifiable concentrate: Active ingredient: 1-95%, preferably 60-90% Surfactant: 1 to 30%, preferably 5 to 20% Liquid carrier: 1 to 80%, preferably 1 to 35%

[0271] Powder for dusting: Active ingredient: 0.1 to 10%, preferably 0.1 to 5% Solid carrier: 99.9 to 90%, preferably 99.9 to 99%

[0272] Suspension concentrate: Active ingredient: 5-75%, preferably 10-50% Water: 94-24%, preferably 88-30% Surfactant: 1 to 40%, preferably 2 to 30%

[0273] Wettable powder: Active ingredient: 0.5 to 90%, preferably 1 to 80% Surfactant: 0.5 to 20%, preferably 1 to 15% Solid carrier: 5 to 95%, preferably 15 to 90%

[0274] Granules: Active ingredient: 0.1 to 30%, preferably 0.1 to 15% Solid carrier: 99.5 to 70%, preferably 97 to 85%

[0275] The disclosure in this application makes available any and all combinations of the embodiments disclosed herein.

[0276] The compounds according to the following Tables B-1 to B-27 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). In any of the following Tables B-1 to B-27, the possible presence of one or more asymmetric carbon atoms in the compound of formula (I) according to the present invention means that the compound can occur in chiral isomeric forms, i.e., enantiomeric or diastereomeric forms.

[0277] Table A: This table discloses 22 compounds of formula (A): [ka] In the formula, R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , B 1 , and B 2 is as defined above for compounds of formula (I), and Q is of the formula [ka] where the dotted line indicates the bond to the rest of the molecule as defined below.

[0278] [Table 1]

[0279] Table B-1: This table lists 22 compounds of formula (A) B-1.01 to B-1.22 (wherein R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 is H and B 1 and B 2 is CH and Q is as defined in Table A).

[0280] For example, compound B-1.17 has the following structure: [ka]

[0281] Table B-2: This table lists 22 compounds of formula (A) B-2.01 to B-2.22 (wherein R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 is H and R 2is CH3 and B 1 and B 2 is CH and Q is as defined in Table A).

[0282] Table B-3: This table lists 22 compounds of formula (A) B-3.01 to B-3.22 (wherein R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 is H and R 2 is CH3 and B 1 is CH, and B 2 is C-Cl, and Q is as defined in Table A).

[0283] Table B-4: This table lists 22 compounds of formula (A) B-4.01 to B-4.22 (wherein R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 is H and R 2 is CH3 and B 1 is CH, and B 2 is C—Br, and Q is as defined in Table A).

[0284] Table B-5: This table lists 22 compounds of formula (A) B-5.01 to B-5.22 (wherein R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 is H and R 2 is CH3 and B 1 is CH, and B 2 is CF and Q is as defined in Table A).

[0285] Table B-6: This table lists 22 compounds of formula (A) B-6.01 to B-6.22 (wherein R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 is H and R 2 is CH3 and B 1 is CH, and B 2 is C-CN, and Q is as defined in Table A).

[0286] Table B-7: This table lists 22 compounds of formula (A) B-7.01 to B-7.22 (wherein R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 is H and R 2 is CH3 and B 1 is CH, and B 2 is C-CH3, and Q is as defined in Table A).

[0287] Table B-8: This table lists 22 compounds of formula (A) racemic-syn-B-8.01 to racemic-syn-B-8.22 (wherein R 2 , R 3 , R 4 , R 5 , R 6 , R 8 , R 9 is H and R 7 is CH3 and B 1 and B 2 is CH, and Q is as defined in Table A. In these compounds, the pyrazole substituent and R 7 The substituents have a syn-relationship to each other.

[0288] For example, rac-syn-B-8.22 has the following structure: [ka]

[0289] Table B-9: This table lists 22 compounds of formula (A) racemic-syn-B-9.01 to racemic-syn-B-9.22 (wherein R 2 , R 3 , R 4 , R 5 , R 6 , R 8 , R 9 is H and R 7 is CH3 and B 1 is CH, and B 2 is C-Cl, and Q is as defined in Table A. In these compounds, the pyrazole substituent and R 7 The substituents have a syn-relationship to each other.

[0290] Table B-10: This table lists 22 compounds of formula (A) racemic-syn-B-10.01 to racemic-syn-B-10.22 (wherein R 2 , R 3 , R 4 , R 5 , R 6 , R 8 , R 9 is H and R 7 is CH3 and B 1 is CH, and B 2 is CF and Q is as defined in Table A. In these compounds, the pyrazole substituent and R 7 The substituents have a syn-relationship to each other.

[0291] Table B-11: This table lists 22 compounds of formula (A) racemic-syn-B-11.01 to racemic-syn-B-11.22 (wherein R 2 , R 3 , R 4 , R 5 , R 6 , R 8 , R 9 is H and R 7 is CH3 and B 1 is CH, and B2 is C—Br, and Q is as defined in Table A. In these compounds, the pyrazole substituent and R 7 The substituents have a syn-relationship to each other.

[0292] Table B-12: This table lists 22 compounds of formula (A) racemic-syn-B-12.01 to racemic-syn-B-12.22 (wherein R 2 , R 3 , R 4 , R 5 , R 6 , R 8 , R 9 is H and R 7 is CH3 and B 1 is CH, and B 2 is C-CN, and Q is as defined in Table A).

[0293] Table B-13: This table lists 22 compounds of formula (A) racemic-syn-B-13.01 to racemic-syn-B-13.22 (wherein R 2 , R 3 , R 4 , R 5 , R 6 , R 8 , R 9 is H and R 7 is CH3 and B 1 is CH, and B 2 is C-CH3, and Q is as defined in Table A).

[0294] Table B-14: This table lists 22 compounds of formula (A) racemic-syn-B-14.01 to racemic-syn-B-14.22 (wherein R 3 , R 4 , R 5 , R 6 , R 8 , R 9 is H and R 2 and R 7 is CH3 and B 1 and B 2is CH, and Q is as defined in Table A. In these compounds, the pyrazole substituent and R 7 The substituents have a syn-relationship to each other.

[0295] For example, rac-syn-B-14.16 has the following structure: [ka]

[0296] Table B-15: This table lists 22 compounds of formula (A) racemic-syn-B-15.01 to racemic-syn-B-15.22 (wherein R 3 , R 4 , R 5 , R 6 , R 8 , R 9 is H and R 2 and R 7 is CH3 and B 1 is CH and B 2 is C-Cl, and Q is as defined in Table A. In these compounds, the pyrazole substituent and R 7 The substituents have a syn-relationship to each other.

[0297] Table B-16: This table lists 22 compounds of formula (A) rac-syn-B-16.01 to racemic-syn-B-16.22 (wherein R 3 , R 4 , R 5 , R 6 , R 8 , R 9 is H and R 2 and R 7 is CH3 and B 1 is CH and B 2 is CF and Q is as defined in Table A. In these compounds, the pyrazole substituent and R 7 The substituents have a syn-relationship to each other.

[0298] Table B-17: This table lists 22 compounds of formula (A) rac-syn-B-17.01 to racemic-syn-B-17.22 (wherein R 3 , R 4 , R 5 , R 6 , R 8 , R 9 is H and R 2 and R 7 is CH3 and B 1 is CH and B 2 is C—Br, and Q is as defined in Table A).

[0299] Table B-18: This table lists 22 compounds of formula (A) rac-syn-syn-B-18.01 to racemic-syn-B-18.22 (wherein R 3 , R 4 , R 5 , R 6 , R 8 , R 9 is H and R 2 and R 7 is CH3 and B 1 is CH and B 2 is C-CN, and Q is as defined in Table A).

[0300] Table B-19: This table lists 22 compounds of formula (A) rac-syn-B-19.01 to racemic-syn-B-19.22 (wherein R 3 , R 4 , R 5 , R 6 , R 8 , R 9 is H and R 2 and R 7 is CH3 and B 1 is CH and B 2 is C-CH3, and Q is as defined in Table A).

[0301] Table B-20: This table lists 22 compounds of formula (A) rac-syn-B-20.01 to racemic-syn-B-20.22, where R 3 , R4 , R 5 , R 6 , R 8 , R 9 is H and R 2 is Cl and R 7 is CH3 and B 1 and B 2 is CH and Q is as defined in Table A).

[0302] Table B-21: This table lists 22 compounds of formula (A) rac-syn-B-21.01 to racemic-syn-B-21.22, where R 3 , R 4 , R 5 , R 6 , R 8 , R 9 is H and R 2 is Cl and R 7 is CH3 and B 1 is CH, and B 2 is C—Br, and Q is as defined in Table A).

[0303] Table B-22: This table lists 22 compounds of formula (A) rac-syn-B-22.01 to racemic-syn-B-22.22, where R 3 , R 4 , R 5 , R 6 , R 8 , R 9 is H and R 2 is Cl and R 7 is CH3 and B 1 is CH, and B 2 is C—Br, and Q is as defined in Table A).

[0304] Table B-23: This table lists 22 compounds of formula (A) rac-syn-B-23.01 to racemic-syn-B-23.22, where R 3 , R 4 , R 5 , R 6 , R 8 , R 9is H and R 2 is Cl and R 7 is CH3 and B 1 is CH, and B 2 is C-CN, and Q is as defined in Table A).

[0305] Table B-24: This table lists 22 compounds of formula (A) B-24.01 to B-24.22 (wherein R 2 , R 3 , R 5 , R 6 , R 7 , R 8 , R 9 is H and R 4 is CH3 and B 1 and B 2 is CH and Q is as defined in Table A).

[0306] Table B-25: This table lists 22 compounds of formula (A) B-25.01 to B-25.22 (wherein R 3 , R 5 , R 6 , R 7 , R 8 , R 9 is H and R 2 and R 4 is CH3 and B 1 and B 2 is CH and Q is as defined in Table A).

[0307] Table B-26: This table lists 22 compounds of formula (A) B-26.01 to B-26.22 (wherein R 3 , R 5 , R 6 , R 7 , R 8 , R 9 is H and R 2 and R 4 is CH3 and B 1 is CH and B 2 is C-Cl, and Q is as defined in Table A).

[0308] Table B-27: This table lists 22 compounds of formula (A) B-27.01 to B-27.22, where R 3 , R 5 , R 6 , R 7 , R 8 , R 9 is H and R 2 and R 4 is CH3 and B 1 is CH and B 2 is C-CN, and Q is as defined in Table A). [Example]

[0309] The following examples are intended to illustrate the present invention but not to limit it in any way.

[0310] The compounds of the present invention are distinguishable from known compounds by their high efficacy at low doses, which can be verified by one skilled in the art using the experimental procedures outlined in the Examples, and where necessary using low doses such as 60 ppm, 20 ppm or 2 ppm.

[0311] Compounds of formula (I) may have many benefits including, inter alia, advantageous levels of biological activity or excellent properties for use as agrochemical active ingredients (e.g., high biological activity, advantageous spectrum of activity, high safety profile (including improved crop tolerance), improved physicochemical properties or high biodegradability) for protecting plants against diseases caused by fungi.

[0312] Throughout this specification, temperatures are given in degrees Celsius and "mp" means melting point. LC-MS means liquid chromatography mass spectrometry, and a description of the equipment and methods follows.

[0313] 1 H NMR and 19 F NMR measurements were recorded on a Bruker 400 MHz spectrometer and chemical shifts were referenced to TMS ( 1H) and CFCl3 ( 19 F) are given in ppm relative to standard. Spectra were taken in deuterated solvents as indicated. Compounds were characterized using one of the following LCMS methods. The characteristic LCMS values ​​obtained for each compound are the retention time ("Rt", recorded in minutes) and the observed molecular ion (M+H). + or (MH) - It was.

[0314] LC-MS 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, ELSD detector. Column: Waters UPLC HSS T3, 1.8 μm, 30 × 2.1 mm; Temperature: 60 °C; DAD wavelength range (nm): 210–500; Solvent gradient: A = water + 5% MeOH + 0.05% HCOOH, B = acetonitrile + 0.05% HCOOH; Gradient: 10–100% B in 1.2 min; Flow rate (ml / min): 0.85.

[0315] LC-MS Method B: Spectra were recorded on a Waters Corporation ACQUITY mass spectrometer (SQD or SQDII single quadrupole mass spectrometer) equipped with an electrospray source (polarity: positive or negative ion, capillary: 3.0 kV, cone: 30 V, extractor: 3.00 V, source temperature: 150 °C, desolvation temperature: 400 °C, cone gas flow: 60 L / hr, desolvation gas flow: 700 L / hr, mass range: 140-800 Da) and a Waters Corporation ACQUITY UPLC equipped with a solvent degasser, binary pump, heated column compartment, and diode array detector. Column: Waters UPLC HSS T3, 1.8 μm, 30 × 2.1 mm; Temperature: 60 °C; DAD wavelength range (nm): 210–400; Solvent gradient: A = water / methanol 9:1 + 0.1% formic acid, B = acetonitrile + 0.1% formic acid; Gradient: 0–100% B in 2.5 min; Flow rate (ml / min): 0.75.

[0316] LC-MS method C: LCMS was recorded on an Agilent 1260 Series LC / MSD system equipped with a DAD\ELSD and an Agilent LC\MSD (G6120B) mass spectrometer, or on a UHPLC Agilent 1290 Series LC / MSD system equipped with a DAD\ELSD and an Agilent LC\MSD (G6125B) mass spectrometer, using specifications; column: Agilent Poroshell 120 SB-C18 4.6 × 30 mm 2.7 μm, column temperature: 60 °C, mobile phase: A - water (0.1% formic acid), B - acetonitrile (0.1% formic acid), flow rate: 3 ml / min, gradient: 0.01 min - 1% B, 1.5 min - 100% B, 1.73 min - 100% B, MS ionization mode: electrospray ionization (ESI), MS scan range: 83-600 m / z, UV detection: 215 nm, 254 nm, 280 nm.

[0317] Example formulation [Table 2]

[0318] This combination is thoroughly mixed with adjuvants and the mixture is thoroughly ground in a suitable mill to give a wettable powder which is diluted with water to give a suspension of the desired concentration.

[0319] [Table 3]

[0320] This combination is thoroughly mixed with the adjuvant and the mixture is thoroughly ground in a suitable mill to obtain a powder that can be used directly as a seed treatment.

[0321] emulsifiable concentrate Active ingredient 10% Octylphenol polyethylene glycol ether (4-5 mol ethylene oxide) 3% Calcium dodecylbenzenesulfonate 3% Castor oil polyglycol ether (35 mol ethylene oxide) 4% Cyclohexanone 30% Xylene mixture 50%

[0322] Emulsions of any desired dilution that can be used for plant protection are obtained from this concentrate by dilution with water.

[0323] [Table 4]

[0324] Ready-to-use dusts are obtained by combining and mixing with a carrier and grinding the mixture in a suitable mill. Such dusting powders can also be used for dry seed dressing.

[0325] Extruded Granules Active ingredient 15% Sodium lignosulfonate 2% Carboxymethylcellulose 1% Kaolin 82%

[0326] This combination is mixed with an adjuvant, ground, and the mixture is wetted with water. The mixture is extruded and then dried in a stream of air.

[0327] Coated Granules Active ingredient 8% Polyethylene glycol (molecular weight 200) 3% Kaolin 89%

[0328] The finely ground combination is applied uniformly in a mixer to kaolin wetted with polyethylene glycol, thus obtaining dust-free coated granules.

[0329] Suspension concentrate Active ingredient 40% Propylene glycol 10% Nonylphenol polyethylene glycol ether (15 mol ethylene oxide) 6% Sodium lignosulfonate 10% Carboxymethylcellulose 1% Silicone oil (in the form of a 75% emulsion in water) 1% water 32%

[0330] The finely ground combination is thoroughly mixed with adjuvants to obtain a suspension concentrate, which can then be diluted with water to obtain a suspension of any desired dilution, and such dilutions can be used to treat and protect living plants and plant propagation material against microbial infestation by spraying, pouring, or dipping.

[0331] Flowable concentrate for seed treatment Active ingredient 40% Propylene glycol 5% Copolymer butanol PO / EO 2% Tristyrenephenol + 10-20 moles of EO 2% 1,2-Benzisothiazolin-3-one (in the form of a 20% aqueous solution) 0.5% Monoazo dye calcium salt 5% Silicone oil (in the form of a 75% emulsion in water) 0.2% Water 45.3%

[0332] The pulverized combination is thoroughly mixed with adjuvants to obtain a flowable concentrate, which can be used directly for seed treatment. The pulverized combination is thoroughly mixed with adjuvants to obtain a flowable concentrate, which can then be diluted with water to obtain any desired dilution. Such dilutions can be used to treat and protect seeds, living plants, and plant propagation material against microbial infestation by spraying, pouring, or dipping.

[0333] Sustained-release capsule suspension 28 parts of the combination are mixed with 2 parts aromatic solvent and 7 parts toluene diisocyanate / polymethylene-polyphenylisocyanate (8:1) mixture. This mixture is emulsified in a mixture of 1.2 parts polyvinyl alcohol, 0.05 parts antifoaming agent, and 51.6 parts water until the desired particle size is achieved. A mixture of 2.8 parts 1,6-diaminohexane in 5.3 parts water is added to this emulsion. The mixture is stirred until the polymerization reaction is complete. The resulting capsule suspension is stabilized by adding 0.25 parts thickener and 3 parts dispersant. This capsule suspension formulation contains 28% active ingredient. The average capsule diameter is 8 to 15 microns. The resulting formulation is applied to seeds as an aqueous suspension in equipment suitable for this purpose.

[0334] Formulation types include emulsion concentrates (EC), suspension concentrates (SC), suspoemulsions (SE), capsule suspensions (CS), water dispersible granules (WG), emulsifiable granules (EG), emulsions, water-in-oil (EO), emulsions, oil-in-water (EW), microemulsions (ME), oil dispersions (OD), oil-miscible flowables (OF), oil-miscible liquids (OL), soluble concentrates (SL), ultra-low volume suspensions (SU), ultra-low volume liquids (UL), technical concentrates (TK), dispersible concentrates (DC), wettable powders (WP), soluble granules (SG) or any technically preferred formulation in combination with an agriculturally acceptable adjuvant.

[0335] Abbreviation CDCl3 deuterated chloroform DABCO 1,4-diazabicyclo[2.2.2]octane, also known as triethylenediamine or TEDA DCC dicyclohexylcarbodiimide DCM dichloromethane or methylene dichloride or methylene chloride DMF Dimethylformamide DMSO dimethyl sulfoxide DMSO-d6 Deuterated dimethyl sulfoxide EDC 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Et3N Triethylamine or TEA EtOAc ethyl acetate HATU 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium-3-oxide-hexafluorophosphate HCl Hydrochloric acid h / hrs time LC-MS Liquid Chromatography Mass Spectrometry (LC-MS or LCMS) rh relative humidity RT room temperature (rt or RT) Rt retention time ssp. subspecies T3P Propanephosphonic Anhydride, also known as 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide THF tetrahydrofuran

[0336] Preparation Examples Compounds of formula (I) according to the invention may be prepared using the synthetic techniques described both above and below.

[0337] "Mp" means melting point (°C). The free radical represents a methyl group. 1 H NMR and 19 F NMR measurements were recorded on a Bruker 400 MHz spectrometer (or 600 MHz spectrometer as indicated) and chemical shifts were expressed in terms of TMS ( 1 H) standard and CFCl3( 19 F) are given in ppm relative to a standard. Spectra were measured in deuterated solvents as indicated. For compound characterization, one of the following LC-MS methods was used: Characteristic LCMS values ​​obtained for each compound were the retention time ("Rt", recorded in minutes) and the observed molecular ion (M+H). + or (MH) - It was.

[0338] Example P1: Preparation of 1-[rac-(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]heptan-1-one (compound P-11, Table P) [ka] Step 1: Preparation of (1,5-dimethylpyrazol-4-yl)-phenyl-methanol [ka] A sample of 1-methyl-1H-pyrazole-4-carbaldehyde (25 g, 201.39 mmol) dissolved in THF (400 mL) was treated dropwise with 1 molar phenylmagnesium bromide in THF (228 mL, 227.57 mmol) at 0–5° C. under an argon atmosphere over 15 min. After the addition, the ice bath was removed, and the white suspension was stirred at rt for 3 h. The reaction mixture was poured into saturated sodium chloride solution and extracted with EtOAc. The combined organic layers were washed with brine, dried over NaSO, and concentrated in vacuo to give the crude product as a colorless oil. The crude material was purified on SiO with an EtOAc:EtOH 3:1 / cyclohexane gradient to give the desired product, (1-methylpyrazol-4-yl)-phenyl-methanol, as a colorless oil. LCMS (Method A): m / z (M+H) 203, retention time 0.68 min 1 H NMR(400MHz,CDCl3)δ ppm:2.23(s,3H)2.28(d,J=4.00Hz,1H)3.76(s,3H)5.80(d,J=3.63Hz,1H)7.22(s,1H)7.27-7.32(m,1H)7.33-7.44(m,4H)

[0339] Step 2: Preparation of 2-(1,5-dimethylpyrazol-4-yl)-2-phenyl-acetonitrile [ka] A round-bottom flask equipped with a magnetic stir bar and a condenser was charged with (1-methylpyrazol-4-yl)-phenyl-methanol (4.5 g, 22 mmol) and DCM (45 mL). Then, lithium carbonate (0.33 g, 4.4 mmol), trimethylsilyl cyanide (10 g, 13 mL, 100 mmol), and iodine (10 g, 40 mmol) were added sequentially at rt. The resulting reaction mixture was stirred at 35 °C for 1 h, cooled to rt, poured into saturated sodium thiosulfate (250 mL), and extracted with DCM (2 × 100 mL). The combined organic layers were washed with brine, dried over NaSO, and concentrated in vacuo to give the crude product, which was purified by combi flash (silica gel, gradient: EtOAc in cyclohexane) to give the desired title compound as a yellow oil. LCMS (Method A): m / z (M+H) 212, retention time 0.82 min 1 H NMR(400MHz,CDCl3-d)δ ppm:7.46-7.28(m,6H),5.05(s,1H),3.78(s,3H),2.18(s,3H)

[0340] Step 3: Preparation of 2-(1,5-dimethylpyrazol-4-yl)-2-phenyl-ethanamine (Option A) [ka] A 750 mL three-neck flask equipped with a magnetic stir bar was charged with 2-(1-methylpyrazol-4-yl)-2-phenylpropanenitrile (11 g, 52.06 mmol) and THF (160 mL). To the yellow solution, borane dimethyl sulfide complex (12.62 g, 15.8 mL, 156.2 mmol) was added dropwise at rt under an argon atmosphere, and the resulting colorless reaction mixture was stirred at 65 °C for 2 h. After the reaction mixture was cooled to 0 °C, HCl (23 g, 34.71 mL, 208.2 mmol) was added dropwise (strong gas evolution), and the mixture was stirred at 65 °C for 1 h and allowed to stand at rt overnight. The mixture was diluted with water and treated with 6 M NaOH (to pH 12). The mixture was extracted twice with EtOAc, and the combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo to give the title compound as a yellow oil, which was used in the next step without further purification. LCMS (Method A): m / z (M+H) 216, retention time 0.60 min 1 H NMR(400MHz,CDCl3)δ ppm:2.09(s,3H)3.20(dd,J=7.45,2.00Hz,2H)3.75(s,3H)3.79(t,J=7.27Hz,1H)7.16-7.25(m,3H)7.26-7.33(m,2H)7.42(s,1H)

[0341] Preparation of 2-(1,5-dimethylpyrazol-4-yl)-2-phenyl-ethanamine (Option B) Option B - Step A: Preparation of 1,5-dimethyl-4-(2-nitro-1-phenyl-ethyl)pyrazole [ka] A solution of 4-iodo-1,5-dimethyl-pyrazole (2.6 g, 12 mmol) in THF (40 mL) was degassed with argon and treated with isopropylmagnesium chloride lithium chloride complex (Turbo Grignard, 1.3 mol / L in THF, 12 mL, 16 mmol) under argon at 0-5 °C. The resulting white suspension was stirred from 0 °C to 5 °C over 20 min and then treated with a solution of [(E)-2-nitrovinyl]benzene (1.5 g, 9.9 mmol) in THF (5 mL) at 0 °C to 5 °C. The mixture was stirred from 0 °C to 5 °C over 40 min and then at rt for 1 h, at which point LCMS analysis indicated completion of the reaction. The reaction mixture was quenched with ice water and acidified to pH 5 by the addition of 2 M aqueous HCl. The aqueous layer was extracted three times with EtOAc, and the combined organic phases were then washed with brine, dried over Na2SO4, and concentrated in vacuo. The crude product was purified by chromatography on silica gel eluting with a gradient of cyclohexane+0-40 EA / EtOH 3:1 to give the title compound. LC-MS (Method A): 246[M+H], Rt: 0.84 min 1 H NMR(400MHz,CDCl3)δ ppm:7.40-7.44(m,1H)7.30-7.36(m,2H)7.23-7.29(m,3H)4.88(d,J=1.1Hz,1H)4.86(s,1H)4.74(d,J=7.6Hz,1H)3.77(s,3H)2.15(s,3H)

[0342] The two enantiomers of the title compound were separated by chiral column using the following method: Sepiatec Prep SFC M5, Column: Daicel CHIRALPAK® IB, 5 μm, 2.0 cm x 25 cm, Mobile phase: A: CO2, B: IPA, Isocratic: 4% B, Back pressure: 150 bar, GLS: -, Flow rate: 90 ml / min, Detection: UV 220 nm, Sample concentration: 1.6 g in 25 ml ACN / MeOH (1 / 1), Injection: 500 μl

[0343] Option B - Step B: Preparation of 2-(1,5-dimethylpyrazol-4-yl)-2-phenyl-ethanamine [ka] A solution of 1,5-dimethyl-4-(2-nitro-1-phenyl-ethyl)pyrazole (35 mg, 0.1427 mmol) in dry ethanol (3 mL) was treated with platinum 1% vanadium 2% on activated carbon (Evonik Noblyst® P8078, 0.00014 mmol, 0.0070 g). The mixture was degassed and hydrogenated at 50° C. and 10 bar H2 for 18 hours. The reaction mixture was filtered through a pad of Celite and evaporated to give the title compound. Spectral data for Example 1, Step 8 above.

[0344] Step 4: Preparation of methyl N-[2-(1,5-dimethylpyrazol-4-yl)-2-phenyl-ethyl]carbamate [ka] A three-necked flask equipped with a mechanical stirrer was charged with 2-(1,5-dimethylpyrazol-4-yl)-2-phenyl-ethanamine (3.5 g, 16 mmol, Option A, sample from Step 8), EtOAc (65 mL), and TEA (6.8 mL, 49 mmol). Methyl chloroformate (1.5 mL, 20 mmol) was then added dropwise at 0 °C under an argon atmosphere over 30 min, and the mixture was stirred at RT for 1 h. The reaction mixture was poured into water (800 mL) and extracted with EtOAc (2 × 150 mL). The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated in vacuo. The crude material was purified by flash chromatography (80 g SiO eluting with an EtOAc / cyclohexane gradient) to give methyl N-[2-(1,5-dimethylpyrazol-4-yl)-2-phenyl-ethyl]carbamate. LC-MS (Method A): Retention time 0.76 min, 274(M+H) 1H NMR(400MHz,CDCl3)δ ppm:2.03-2.13(m,3H)3.62-3.74(m,5H)3.77(s,3H)3.94-4.05(m,1H)4.72(br s,1H)7.21-7.26(m,3H)7.27-7.34(m,2H)7.38(s,1H)

[0345] Step 5: Preparation of methyl rac-(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylate [ka] A single-neck round-bottom flask equipped with a magnetic stir bar was charged with methyl N-[2-(1,5-dimethylpyrazol-4-yl)-2-phenyl-ethyl]carbamate (2.0 g, 7.3 mmol), hydrochloric acid (concentrated, 37 mL, 450 mmol), and acetaldehyde (0.83 mL, 15 mmol). The mixture was stirred at RT for 2 h. The reaction mixture was slowly poured into water (500 mL) and slowly neutralized to pH 8 with NaHCO3 in several portions (strong gas evolution). The mixture was extracted with EtOAc (3 × 50 mL), and the combined organic layers were washed with brine, dried over sodium sulfate, and concentrated in vacuo. The crude product was purified by chromatography to give rac-methyl (1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylate as a single syn-diastereomer. 1 1 H NMR. LC-MS (Method A): Retention time 0.87 min, 300(M+H) 1 H NMR(400MHz,CDCl3)δ ppm:1.56(d,J=6.90Hz,3H);2.18(br s,3H);3.02-3.27(m,1H);3.76(br s,3H);3.83(s,3H);3.97-4.09(m,1H);4.09-4.37(m,1H);5.18-5.45(m,1H);6.86-7.02(m,1H);7.04-7.24(m,4H).

[0346] Step 6: Preparation of rac-(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-1,2,3,4-tetrahydroisoquinoline [ka] A 100 mL single-neck flask equipped with a magnetic stir bar was charged with rac-methyl (1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylate (1.3 g, 4.1 mmol), 1,2-dichloroethane (21 mL), and iodotrimethylsilane (1.7 mL, 12 mmol). The mixture was stirred at 60° C. for 1 hour under an argon atmosphere. The reaction was cooled to rt, and then 10% aqueous HCl (22 mL) was added to the reaction under ice cooling. The organic solvent was removed in vacuo, and the aqueous residue was adjusted to pH 8 with 10% aqueous NaOH, then extracted with DCM. The combined organic layers were collected by filtration. g Extraction with SO4, filtration, and concentration in vacuo gave rac-(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-1,2,3,4-tetrahydroisoquinoline, which was sufficiently pure to be used without further purification. LC-MS (Method A): Retention time 0.35 min, 242(M+H) 1 H NMR(600MHz,CDCl3)δ ppm:1.86(d,J=6.9Hz,3H)2.23(s,3H)3.27(dd,J=12.5,10.8Hz,1H)3.59(dd,J=12.8,5.6Hz,1H)3.83(s,3H)4.58(dd,J=10. 6,5.4Hz,1H)4.80(q,J=6.8Hz,1H)7.00(d,J=7.8Hz,1H)7.11(s,1H)7.16(d,J=7.6Hz,1H)7.18-7.22(m,1H)7.25-7.28(m,1H)

[0347] Step 7: Preparation of 1-[rac-(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]heptan-1-one (Compound P-11, Table P) A 30 mL vial equipped with a magnetic stir bar was charged with rac-(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-1,2,3,4-tetrahydroisoquinoline (100 mg, 0.41 mmol), N-ethyl-N-isopropylpropan-2-amine (0.284 mL, 1.7 mmol), heptanoic acid (62 mg, 0.46 mmol), and EtOAc (2.1 mL). T3P 50% in EtOAc (0.49 mL, 0.83 mmol) was added at RT, and the resulting reaction mixture was stirred at 55 °C for 35 min. After cooling to RT, the mixture was diluted with EtOAc, quenched with NaHCO3, and extracted with EtOAc. The combined organic layers were washed with water and brine, dried over sodium sulfate, and concentrated in vacuo. The crude product was purified by chromatography to give the title compound, which was further purified by reverse phase chromatography to give pure 1-[(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]heptan-1-one. LC-MS (Method A): Retention time 0.89 min, 354(M+H) 1 H NMR(400MHz,CDCl3)δ ppm:0.83-0.98(m,3H),1.21-1.45(m,7H),1.55(d,J=6.9Hz,2H),1.61-1. 73(m,3H),2.20(d,J=15.6Hz,3H),2.34-2.53(m,2H),3.45(dd,J=13.8,12 .0Hz,1H),3.87(d,J=4.7Hz,3H),3.98-4.08(m,1H),5.80(q,J=6.9Hz,1H) ,6.91(d,J=8.0Hz,1H),7.08-7.22(m,2H),7.27-7.31(m,1H),8.13(s,1H).

[0348] Example P2: Preparation of 7,7,7-trifluoro-1-[rac-(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]heptan-1-one (compound P-29, Table P) [ka] Step 1: Preparation of methyl (E)-7,7,7-trifluorohept-2-enoate [ka] A solution of DMSO (1.5 mL, 21 mmol) in DCM (28 mL) was cooled to −78° C. under argon. Oxalyl chloride (1.3 mL, 14 mmol) was added dropwise, resulting in exotherm and gas formation. The resulting solution was stirred at −78° C. for 15 minutes, and then 5,5,5-trifluoropentan-1-ol (1.0 g, 7.0 mmol) was added dropwise. This was stirred at −78° C. for 30 minutes, followed by the dropwise addition of triethylamine (4.0 mL, 28 mmol). Stirring was continued for 10 minutes, then it was allowed to warm to RT and stirred for an additional 30 minutes under argon. The intermediate 5,5,5-trifluoropentanal was formed. Methyl(triphenylphosphoranylidene)acetate (2.5 g, 7.4 mmol) was added portionwise to the solution, and the resulting reaction mixture was stirred at RT for 2 hours and 30 minutes before being dissolved in water and pentane. The organic phase containing methyl (E)-7,7,7-trifluorohept-2-enoate was separated and used in the next step without evaporation.

[0349] Step 2: Preparation of (E)-7,7,7-trifluorohept-2-enoic acid [ka] To a solution of methyl (E)-7,7,7-trifluorohept-2-enoate (1.4 g, 7.0 mmol) in pentane was added THF (35 mL) and water (7.0 mL), followed by lithium hydroxide (511 mg, 21 mmol). The resulting reaction mixture was stirred at RT for 3 days, then EtOAc, water, and HCl 1N were added until the pH reached 1 to 2, and the aqueous phase was extracted with EtOAc. The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated in vacuo to afford (E)-7,7,7-trifluorohept-2-enoic acid without further purification. LC-MS (Method A): Retention time 1.05 min, 181(MH) 1 H NMR(400MHz,CDCl3)δ ppm 1.73-1.88(m,2H)2.04-2.22(m,2H)2.36(q,J=7.39Hz,2H)5.90(dt,J=15.62,1.63Hz,1H)7.05(dt,J=15.62,6.90Hz,1H).

[0350] Step 3: Preparation of rac-(E)-7,7,7-trifluoro-1-[rac-(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]hept-2-en-1-one [ka] To a solution of rac-(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-1,2,3,4-tetrahydroisoquinoline (prepared as above) (200 mg, 0.58 mmol) and (E)-7,7,7-trifluorohept-2-enoic acid (127 mg, 0.70 mmol) in 2.9 mL of EtOAc under argon, 1-propanephosphonic anhydride (0.69 mL, 1.2 mmol) was added, followed by N,N-diisopropylethylamine (0.30 mL, 1.7 mmol). The reaction mixture was stirred at RT for 1 h. NaHCO3 and EtOAc were added, and then this was extracted with additional EtOAc. The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. The crude product was purified by chromatography to give rac-(E)-7,7,7-trifluoro-1-[rac-(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]hept-2-en-1-one. LC-MS (Method A): Retention time 1.01 min, 406(M+H) 1H NMR(400MHz,CDCl3)δ ppm 1.58-1.65(m,2H),1.68(br d,J=6.9Hz,2H),1.72-1.84(m,3H),2.02-2.16(m,2H),2.16-2.24(m,3H),2.30-2.39(m,2H),3.86(s,3H),4.01-4.09(m ,1H),5.73-5.93(m,1H),6.32-6.45(m,1H),6.85-7.04(m,2H),7.09-7.18(m,1H),7.18-7.26(m,2H),7.44-7.60(m,1H)

[0351] Step 4: Preparation of 7,7,7-trifluoro-1-[rac-(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]heptan-1-one (Compound P-29, Table P) A solution of rac-(E)-7,7,7-trifluoro-1-[rac-(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]hept-2-en-1-one (70 mg, 0.17 mmol) in ethanol (3.5 mL) was hydrogenated twice in full H mode in an H-Cube with a Pd / C cartridge at 60° C. The reaction mixture was evaporated and purified by chromatography to give 7,7,7-trifluoro-1-[rac-(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]heptan-1-one. LC-MS (Method A): Retention time 1.04 min, 408(M+H)

[0352] Example P3: Preparation of pentyl rac-(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylate (compound P-28, Table P) [ka] A mixture of rac-(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-1,2,3,4-tetrahydroisoquinoline (prepared as described above) (50 mg, 0.21 mmol) and N,N-diisopropylethylamine (0.091 mL, 0.52 mmol) in 2-methyltetrahydrofuran (0.83 mL) was carefully treated with triphosgene (31 mg, 0.10 mmol) under argon at 0°C. The resulting reaction mixture was stirred at 0°C for 2 hours. 1-Pentanol (0.057 mL, 0.52 mmol) was added and stirring was continued at RT overnight. The reaction mixture was transferred to a microwave vial, and another portion of 1-pentanol (0.11 mL) was added. The vial was placed in a microwave and stirred at 150°C for 1 hour. Another portion of 1-pentanol (0.22 mL) was added, and it was stirred again in a microwave at 150° C. for 1 hour. The reaction mixture was then cooled, diluted with EtOAc, and washed with water and brine. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The crude product was purified by reverse-phase chromatography to give pentyl rac-(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylate. LC-MS (Method A): Retention time 1.13 min, 357(M+H) 1 H NMR(400MHz,CDCl3)δ ppm 0.88-0.99(m,3H),1.38(br d,J=3.3Hz,4H),1.57(d,J=6.9Hz,3H),1.61-1.76(m,2H),2.19(br s,3H),3.84(s,3H),3.97-4.08(m,1H),4.08-4.22(m,3H),4.24-4.42(m,1H) ,5.20-5.51(m,1H),6.89-7.03(m,1H),7.06-7.14(m,1H),7.15-7.24(m,3H).

[0353] Example P4: Preparation of 2-cyclohexylethyl rac-(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylate (Compound P-16, Table P) [ka] Step 1: Preparation of 2-cyclohexylethylimidazole-1-carboxylate [ka] To a solution of CDI (1.6 g, 9.6 mmol) in THF (20 mL) was added 2-cyclohexylethanol (1.1 mL, 7.6 mmol) dropwise at RT. The reaction mixture was stirred at RT for 24 h, then diluted with EtOAc and carefully quenched with water. The mixture was then extracted with EtOAc, and the combined organic layers were washed with water, brine, dried over sodium sulfate, and concentrated in vacuo to give 2-cyclohexylethylimidazole-1-carboxylate. LC-MS (Method A): Retention time 0.98 min, 223(M+H) 1 H NMR(400MHz,CDCl3)δ ppm 0.89-1.07(m,3H),1.12-1.36(m,5H),1.36-1.54(m,2H),1.74-1.80(m,3H), 4.47(t,J=6.9Hz,2H),7.44(t,J=1.5Hz,1H),7.71(s,1H),8.14-8.17(m,1H).

[0354] Step 2: 2-Cyclohexylethyl 3-methylimidazol-3-ium-1-carboxylate; Preparation of the iodide [ka] A solution of 2-cyclohexylethylimidazole-1-carboxylate (0.50 g, 2.3 mmol) in acetonitrile (5.0 mL) was prepared in a vial, and iodomethane (0.71 mL, 11.2 mmol) was added. The tube was sealed, and the reaction mixture was stirred at RT overnight and at 40 °C for 6 h. The solvent was evaporated, and the crude 2-cyclohexylethyl 3-methylimidazol-3-ium-1-carboxylate iodide was used in the next step without further purification. LC-MS (Method A): Retention time 0.70 min, 237(M+H)

[0355] Step 3: Preparation of 2-cyclohexylethyl-rac-(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylate (Compound P-16, Table P) In a vial, rac-(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-1,2,3,4-tetrahydroisoquinoline (prepared as described above) (65 mg, 0.27 mmol) was dissolved in acetonitrile (0.65 mL). To this solution, 2-cyclohexylethyl 3-methylimidazol-3-ium-1-carboxylate; iodide (184 mg, 0.40 mmol) and triethylamine (0.094 mL, 0.67 mmol) were added, and the mixture was stirred at RT for 2 hours. The reaction mixture was then diluted with EtOAc, quenched with water, and extracted with EtOAc. The combined organic layers were washed with water and brine, dried over sodium sulfate, and concentrated in vacuo. The crude product was purified by chromatography to give 2-cyclohexylethyl-rac-(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-3,4-dihydro-1H-isoquinoline-2-carboxylate. LC-MS (Method A): Retention time 1.22 min, 396(M+H) 1 H NMR(400MHz,CDCl3)δ ppm 0.88-1.04(m,2H),1.13-1.31(m,3H),1.33-1.47(m,1H),1.51-1.61(m,5H),1.62-1.80(m,5H),2.17(br s,3H),3.02-3.25(m,1H),3.83(s,3H),3.97-4.09(m,1H),4.09-4.37(m,3H),5.21-5.47(m,1H),6.90-7.01(m,1H),7.09(br s,1H),7.12-7.25(m,3H).

[0356] Example P5: Preparation of 4-(1,5-dimethylpyrazol-4-yl)-N-pentyl-3,4-dihydro-1H-isoquinoline-2-carboxamide (Compound P-31, Table P) [ka] Step 1: Preparation of 4-(1,5-dimethylpyrazol-4-yl)isoquinoline [ka] A suspension of 4-bromoisoquinoline (2.0 g, 9.4204 mmol), 1,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (2.3484 g, 10.362 mmol), and potassium carbonate (1.4322 g, 10.362 mmol) in a toluene / methanol mixture (30 mL, 5:1) in a microwave vial was degassed with argon for several minutes, and then tetrakis(triphenylphosphaniumyl)palladium (0.545 g, 0.471 mmol) was added. The reaction mixture was heated to 100 °C and stirred under microwave irradiation for 1 hour. After cooling to room temperature, the reaction mixture was partitioned between water and EtOAc, and the organic layer was separated, dried over Na SO , filtered, and concentrated in vacuo. Purification of the crude material by flash chromatography on silica gel (eluting with EtOAc / 30% methanol) afforded the title compound. LCMS (Method A): m / z225[M+H], retention time 0.51 min

[0357] Step 2: Preparation of 4-(1,5-dimethylpyrazol-4-yl)-1,2,3,4-tetrahydroisoquinoline [ka] To a solution of 4-(1,5-dimethylpyrazol-4-yl)isoquinoline (2.00 g, 8.96 mmol) in methanol (90 mL) was added sodium cyanoborohydride (3.55 g, 53.7 mmol) at room temperature. The reaction mixture was stirred at RT, and then HCl (1.25 M in methanol) was added until a pH of 2-3 was reached. After stirring at RT for 30 min, the reaction mixture was diluted with water, basified with 2 N NaOH, and the mixture was extracted with EtOAc (3 times). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The resulting yellow oil was used without further purification. LCMS (Method A): m / z228[M+H]. Retention time 0.29 minutes

[0358] The hydrochloride salt of the title product (4-(1,5-dimethylpyrazol-4-yl)-1,2,3,4-tetrahydroisoquinoline; hydrochloride) could be obtained by treating the yellow oil with 2M HCl in diethyl ether followed by concentration in vacuo.

[0359] Step 3: Preparation of N-pentylimidazole-1-carboxamide [ka] To a solution of CDI (1.0 g, 6.0 mmol) in THF (10 mL) was added pentan-1-amine (0.66 mL, 5.5 mmol) dropwise at 0 °C. The reaction mixture was stirred at RT overnight, then diluted with EtOAc and carefully quenched with water. The mixture was then extracted with EtOAc, and the combined organic layers were washed with water, brine, dried over sodium sulfate, and concentrated in vacuo to give N-pentylimidazole-1-carboxamide, which was used in the next step without further purification. LC-MS (Method A): Retention time 0.57 min, 182(M+H)

[0360] Step 4: Preparation of 4-(1,5-dimethylpyrazol-4-yl)-N-pentyl-3,4-dihydro-1H-isoquinoline-2-carboxamide (Compound P-31, Table P) In a vial, 4-(1,5-dimethylpyrazol-4-yl)-1,2,3,4-tetrahydroisoquinoline (prepared as above) (0.25 g, 0.88 mmol) was dissolved in acetonitrile (6.3 mL) and cooled to 0 °C. This was then treated with N-pentylimidazole-1-carboxamide (0.18 g, 0.88 mmol), triethylamine (0.25 mL, 1.8 mmol), and DMAP (0.11 g, 0.88 mmol) and allowed to stir at RT for 48 h. The reaction mixture was diluted with EtOAc, quenched with water, and extracted with EtOAc. The combined organic layers were washed with water and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The crude product was purified by chromatography to give the title compound, which was further purified by reverse phase chromatography to give pure 4-(1,5-dimethylpyrazol-4-yl)-N-pentyl-3,4-dihydro-1H-isoquinoline-2-carboxamide. LC-MS (Method A): Retention time 0.91 min, 341(M+H) 1 H NMR(400MHz,CDCl3)δ ppm 0.90(t,J=7.1Hz,3H),1.24-1.40(m,4H),1.49(quin,J=7.2Hz,2H),2.17(s,3 H),3.20-3.28(m,2H),3.42(dd,J=8.5,12.5Hz,1H),3.81(s,3H),3.89(dd,J= 4.5,12.5Hz,1H),4.07(dd,J=4.7,8.4Hz,1H),4.38(br t,J= 5.1Hz,1H),4.54-4.76(m,2H),6.99(d,J=7.6Hz,1H),7.13(s,1H),7.14-7.25(m,3H).

[0361] Example P6: Preparation of rac-(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-N-pentyl-3,4-dihydro-1H-isoquinoline-2-carboxamide (Compound P-43, Table P) [ka] A suspension of rac-(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-1,2,3,4-tetrahydroisoquinoline (prepared as described above) (50 mg, 0.21 mmol) and N,N-diisopropylethylamine (0.091 mL, 0.52 mmol) in 2-methyltetrahydrofuran (0.83 mL) was carefully treated with triphosgene (31 mg, 0.10 mmol) under argon at 0° C. The reaction mixture was allowed to stir at 0° C. for 2 hours, then amylamine (0.062 mL, 0.52 mmol) was added, and the resulting reaction mixture was stirred at RT overnight. After 2 hours, another portion of amylamine (0.062 mL, 0.52 mmol) was added. After the reaction was complete, the reaction mixture was diluted with EtOAc and washed with water and brine. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The crude material was purified by reverse phase chromatography to give pure rac-(1S,4S)-4-(1,5-dimethylpyrazol-4-yl)-1-methyl-N-pentyl-3,4-dihydro-1H-isoquinoline-2-carboxamide. LC-MS (Method A): Retention time 0.96 min, 355(M+H) 1 H NMR(400MHz,CDCl3)δ ppm 0.92(t,J=6.9Hz,3H),1.30-1.38(m,4H),1.50-1.57(m,2H),1.59(d,J=6.9Hz,3H),2.18(s, 3H),3.06-3.22(m,1H),3.29(dt,J=7.4,5.6Hz,2H),3.84(s,3H),4.02-4.18(m,2H),4.56(br s,1H),5.12(q,J=6.9Hz,1H),6.96(d,J=8.0Hz,1H),7.07-7.23(m,4H).

[0362] Example P7: Preparation of 2-(2,4-difluorophenyl)sulfanyl-1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]ethanone (compound P-14, Table P) [ka] Step 1: Preparation of 2-chloro-1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]ethanone [ka] In a round-bottom flask, 4-(1,5-dimethylpyrazol-4-yl)-1,2,3,4-tetrahydroisoquinoline (prepared as above) (1.1 g, 5.0 mmol) was dissolved in THF (15 mL) and cooled to 0 °C. Triethylamine (1.4 mL, 10 mmol) was added dropwise, followed by 2-chloroacetyl chloride (0.40 mL, 5.0 mmol). After stirring at 0 °C for 40 min, it was warmed to RT and stirring was continued for 2.5 h. The reaction mixture was quenched with water and extracted with EtOAc. The combined organic layers were washed with water and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The crude product was purified by chromatography to give 2-chloro-1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]ethanone. LC-MS (Method A): Retention time 0.77 min, 304(M+H) 1 H NMR(400MHz,CDCl3)δ ppm 2.15-2.38(m,3H),3.83(s,3H),3.87-4.04(m,2H),4.04-4.27(m,3H),4.81(s,2H),6.96-7.11(m,1H),7.11-7.34(m,4H).

[0363] Step 2: Preparation of 2-(2,4-difluorophenyl)sulfanyl-1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]ethanone (Compound P-16, Table P) In a vial, 2,4-difluorobenzenethiol (CAS: 1996-44-7) (50 mg, 0.34 mmol), potassium iodide (2.8 mg, 0.017 mmol), and dipotassium carbonate (71 mg, 0.50 mmol) were combined with acetone (0.75 mL). After stirring at RT for 5 minutes, 2-chloro-1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]ethanone (112 mg, 0.37 mmol) diluted with acetone (0.50 mL) was added, and the mixture was stirred overnight at RT. The reaction mixture was then extracted with EtOAc and water. The combined organic layers were washed with water and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The crude product was purified by chromatography and further purified by reverse phase chromatography to give pure 2-(2,4-difluorophenyl)sulfanyl-1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]ethanone. LC-MS (Method A): Retention time 0.96 min, 414(M+H) 1 H NMR(400MHz,CDCl3)δ ppm 2.13-2.28(m,3H),3.53-3.67(m,2H),3.71-3.80(m,1H),3.80-3.85(m,3H),3.85-4.03(m,1H),4.11-4.3 5(m,1H),4.68-4.96(m,2H),6.78-6.90(m,2H),6.94-7.06(m,1H),7.12-7.29(m,4H),7.30-7.54(m,1H).

[0364] Example P8: Preparation of 3-(2,4-difluorophenyl)-1-[4-(1-methylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]propan-1-one (compound P-1, Table P) [ka] A mixture of 3-(2,4-difluorophenyl)propionic acid (CAS 134672-70-1) (0.10 g, 0.52 mmol), 4-(1-methylpyrazol-4-yl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (CAS 2303565-69-5) (0.14 g, 0.57 mmol), and HATU (0.25 g, 0.63 mmol) was dissolved in DMF (2.6 mL). Then, TEA (0.29 mL, 2.1 mmol) was added, and the resulting reaction mixture was stirred overnight at RT. It was quenched with aqueous ammonium chloride solution and extracted with DCM. The combined organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The crude product was purified by reverse phase chromatography to give 3-(2,4-difluorophenyl)-1-[4-(1-methylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]propan-1-one. LC-MS (Method A): Retention time 0.99 min, 382(M+H) 1 H NMR(400MHz,DMSO-d6)δ ppm 2.24-2.40(m,1H),2.70-2.84(m,2H),3.69-3.81(m,5H),4.16(s,1H),4. 51(d,J=17.2Hz,1H),4.72(d,J=14.3Hz,1H),4.82-4.89(m,1H),7.03(br d,J=7.7Hz,2H),7.12-7.30(m,6H),7.37-7.46(m,1H).

[0365] Example P9: Preparation of 3-(2,4-difluorophenyl)-1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]propan-1-one (compound P-6, Table P) [ka] Step 1: Preparation of 1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]prop-2-en-1-one [ka] A sample of 4-(1,5-dimethylpyrazol-4-yl)-1,2,3,4-tetrahydroisoquinoline (1.80 g, 7.92 mmol) dissolved in EtOAc (54.0 mL) was treated with pyridine (3.20 g, 3.26 mL, 39.6 mmol), and the solution was then treated with acryloyl chloride (0.887 g, 0.796 mL, 9.50 mmol). The resulting organic suspension was stirred under nitrogen at rt overnight. The mixture was quenched with NaHCO3 solution and extracted with EtOAc. The organic layer was washed once with water and once with brine, dried over Na2SO4, filtered, and evaporated in vacuo. The crude product was dissolved in EtOAc, adsorbed onto isolute® and purified on a silica gel cartridge (Rf200) to give 1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]prop-2-en-1-one. LC / MS:282[M+H]+; Retention time: 0.74 min (Method A)

[0366] Step 2: Preparation of 3-(2,4-difluorophenyl)-1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]propan-1-one (Compound P-6, Table P) Tris(triphenylphosphine)rhodium(I) chloride (4.69 mg, 0.00506 mmol), KPO (43.4 mg, 0.203 mmol), and (R)-(+)-2,2'-BINAP (3.25 mg, 0.00506 mmol) dissolved in 1,4-dioxane (0.9 mL) were degassed under argon for 15 minutes. To this solution were added 1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]prop-2-en-1-one (30.0 mg, 0.101 mmol) and 2,4-difluorophenylboronic acid (33.0 mg, 0.203 mmol), and the mixture was heated to 60 °C overnight. The reaction mixture was loaded directly onto isolute® and purified on a silica gel cartridge to give the title compound. LC / MS standard: 396[M+H]+; retention time: 0.95 min

[0367] Example P10: Preparation of 2-(2,4-difluorophenoxy)-1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]ethanone (compound P-13, Table P) [ka] In a vial, 2,4-difluorophenol (50 mg, 0.38 mmol), potassium iodide (3.2 mg, 0.019 mmol), and dipotassium carbonate (80 mg, 0.57 mmol) were combined with acetone (0.75 mL). After stirring at RT for 5 minutes, 2-chloro-1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]ethanone (prepared as described above in Example P7, Step 1) (0.13 g, 0.42 mmol) diluted with acetone (0.5 mL) was added, and the mixture was stirred overnight at RT. The reaction mixture was then extracted with water and EtOAc, and the combined organic layers were washed with water and brine, dried over sodium sulfate, and concentrated in vacuo. The crude product was purified by chromatography and further purified by reverse phase chromatography to give pure 2-(2,4-difluorophenoxy)-1-[4-(1,5-dimethylpyrazol-4-yl)-3,4-dihydro-1H-isoquinolin-2-yl]ethanone. LC-MS (Method A): Retention time 0.93 min, 398(M+H)

[0368] Further examples of compounds of formula (I) that have been synthesized are shown in Table P.

[0369] [Table 5-1]

[0370] [Table 5-2]

[0371] [Table 5-3]

[0372] Table 5-4

[0373] Table 5-5

[0374] Table 5-6

[0375] Table 5-7

[0376] Table 5-8

[0377] Table 5-9

[0378] Table 5-10

[0379] examples of biology Example B1: Alternaria solani / Tomat / leaves (summer blight) Tomato leaf discs (cv. Baby) were placed on agar in a multiwell plate (24-well format) and sprayed with the formulated test compound diluted in water. The discs were inoculated with a fungal spore suspension two days after application. The inoculated discs were incubated in a climate cabinet at 23°C / 21°C (day / night) under a 12 / 12 h light / dark photoperiod and 80% relative humidity. When an appropriate level of disease damage had developed on the untreated test discs (5-7 days after application), the efficacy of the compound was evaluated as the percentage of disease control compared to the untreated ones.

[0380] The following compounds provided at least 80% control of Alternaria solani at 200 ppm when compa...

Claims

1. Compounds of formula (I) 【Chemistry 1】 (In the formula, R 1 But hydrogen, C 1 ~C 4 -Alkyl, C 2 ~C 4 -alkenyl, C 2 ~C 4 -alkynyl, or C 3 ~C 6 -cycloalkyl; R 2 But hydrogen, halogen, C 1 ~C 4 -Alkyl, C 2 ~C 4 -alkenyl, C 2 ~C 4 -alkynyl, C 1 ~C 4 -haloalkyl, C 3 ~C 6 -cycloalkyl, C 1 ~C 4 -Alkylcarbonyl, N—C 1 ~C 4 -alkoxy-C-C 1 ~C 4 -Alkyl-carbonimidoyl, N-hydroxy-C-C 1 ~C 4 Alkyl-carbonimidoyl, or C 1 ~C 4 -alkoxycarbonyl; R 3 But hydrogen, halogen, C 1 ~C 4 -haloalkyl, or C 1 ~C 4 - selected from alkyl; R 4 But hydrogen, halogen, C 1 ~C 4 -haloalkyl, C 3 ~C 6 -cycloalkyl, or C 1 ~C 4 - selected from alkyl; R 5 and R 6 is hydrogen or C 1 ~C 4 - independently selected from alkyl; R 7 But hydrogen, C 1 ~C 4 -Alkyl, C 1 ~C 4 -Alkylcarbonyl, N—C 1 ~C 4 -alkoxy-C-C 1 ~C 4 -Alkyl-carbonimidoyl, N-hydroxy-C-C 1 ~C 4 -Alkyl-carbonimidoyl, C 1 ~C 4 -alkoxycarbonyl, N-methoxy-N-methyl-carbonyl, C 1 ~C 4 -Alkylaminocarbonyl, di(C 1 ~C 4 -alkylamino)carbonyl, phenyl, 5- to 6-membered heteroaryl, or C 3 ~C 6 -cycloalkyl; said 5- to 6-membered heteroaryl contains 1, 2, 3 or 4 identical or different heteroatoms selected from N, O or S, provided that only one is O or S; said phenyl and 5- to 6-membered heteroaryl are unsubstituted or selected from halogen, C 1 ~C 4 -haloalkyl, cyano, carboxy, C 1 ~C 4 -Alkyl and C 1 ~C 4 -substituted with 1, 2 or 3 identical or different substituents selected from the group consisting of -alkoxy; 3 ~C 6 - cycloalkyl is unsubstituted or halogen, C 1 ~C 4 -haloalkyl, cyano, C 1 ~C 4 - alkyl, or C 1 ~C 4 -substituted with 1, 2 or 3 identical or different substituents selected from the group consisting of alkoxy; B 1 But, CR 10 or N; B 2 But, CR 11 or N; R 8 , R 9 , R 10 and R 11 But hydrogen, halogen, C 1 ~C 4 -Alkyl, C 1 ~C 4 -haloalkyl, C 1 ~C 4 -alkoxy, C 1 ~C 4 -haloalkoxy, C 2 ~C 4 -alkenyloxy, C 2 ~C 4 -alkynyloxy, C 1 ~C 4 - alkylsulfanyl, C 1 ~C 4 Alkylsulfinyl, C 1 ~C 4 - alkylsulfonyl, C 1 ~C 4 -alkoxy-C 1 ~C 4 -Alkyl, N—C 1 ~C 4 -Alkylamino, N,N-di(C 1 ~C 4 -alkyl)amino, C 1 ~C 4 -alkoxycarbonyl, C 1 ~C 4 -Alkylcarbonyl, N—C 1 ~C 4 -alkoxy-C 1 ~C 4 -Alkyl-carbonimidoyl, N-hydroxy-C 1 ~C 4 alkyl-carbonimidoyl, hydroxy, trifluoromethylsulfonyloxy, cyano, carboxy, amino, phenyl, 5- to 6-membered heteroaryl, or C 3 ~C 6 cycloalkyl; said 5- to 6-membered heteroaryl contains 1, 2, 3 or 4 identical or different heteroatoms selected from N, O, or S, provided that only one is O or S; said phenyl, 5- to 6-membered heteroaryl, and C 3 ~C 6 - any of the cycloalkyl is unsubstituted or is selected from halogen, cyano, C 1 ~C 4 -Alkyl, C 1 ~C 4 -haloalkyl, and C 1 ~C 4 -substituted with 1, 2, 3 or up to the maximum possible number of identical or different substituents selected from the group consisting of alkoxy; W is O, N, S, *-CH 2 O- # , "-CH 2 NH- # , "-CH 2 S- # or a bond, where the star (*) indicates the position of attachment to the carbonyl group, and # indicates Z 1 indicates the position of connection to Z 1 But C 1 ~C 6 alkyl, phenyl, or 6-membered heteroaryl; 1 ~C 6 - alkyl is unsubstituted or halogen, C 1 ~C 4 -Alkyl, C 2 ~C 4 -alkenyl, C 2 ~C 4 -alkynyl, C 1 ~C 4 -haloalkyl, C 1 ~C 4 -alkoxy, C 1 ~C 4 -haloalkoxy, C 2 ~C 4 -alkenyloxy, C 2 ~C 4 -alkynyloxy, C 1 ~C 4 - alkylsulfanyl, C 1 ~C 4 -Alkylsulfinyl, C 1 ~C 4 - alkylsulfonyl, C 1 ~C 4 -alkoxy-C 1 ~C 4 -Alkyl, C 1 ~C 4 -alkoxycarbonyl, C 1 ~C 4 -Alkylcarbonyl, N—C 1 ~C 4 -alkoxy-C-C 1 ~C 4 -Alkyl-carbonimidoyl, N-hydroxy-C-C 1 ~C 4 -alkyl-carbonimidoyl, hydroxy, trifluoromethylsulfonyloxy, cyano, carboxy, phenyl, a 5- to 6-membered saturated or partially saturated heterocycle, a 5- to 6-membered heteroaryl, or C 3 ~C 6 -cycloalkyl; any of the 6-membered heteroaryl and the 5- to 6-membered heteroaryl contain 1, 2 or 3 of the same or different heteroatoms selected from N, O or S, provided that only one is O or S; any of the 5- to 6-membered saturated or partially saturated heterocycle contains 1, 2 or 3 of the same or different heteroatoms selected from N, O or S, provided that only one is O or S; any of the phenyl, any of the 6-membered heteroaryl, any of the 5- to 6-membered heteroaryl, and any of the 5- to 6-membered saturated or partially saturated heterocycle is unsubstituted or is substituted with halogen, cyano, C 1 ~C 4 -Alkyl, C 1 ~C 4 -haloalkyl, C 3 ~C 6 -cycloalkyl, and C 1 ~C 4 -substituted with 1, 2, 3 or up to the maximum possible number of the same or different substituents selected from the group consisting of -alkoxy; 3 ~C 6 - any of the cycloalkyl is unsubstituted or is selected from halogen, cyano, C 1 ~C 4 -Alkyl, C 1 ~C 4 -haloalkyl, and C 1 ~C 4 -substituted with 1, 2, 3 or up to the maximum possible number of identical or different substituents selected from the group consisting of -alkoxy); or an agrochemically acceptable salt, stereoisomer, or N-oxide thereof, provided that the compound of formula (I) is 【Chemistry 2】 【Transformation 3】 or an agrochemically acceptable salt, stereoisomer, or N-oxide thereof, provided that the compound of formula (I) is not an agrochemically acceptable salt, stereoisomer, enantiomer, tautomer, or N-oxide thereof.

2. R 1 is methyl, and R 3 , R 5 , R 6 2. The compound of formula (I) according to claim 1, wherein is hydrogen.

3. R 2 is hydrogen, halogen, or C 1 ~C 4 3. The compound of formula (I) according to claim 1 or 2, wherein - alkyl.

4. R 4 is hydrogen or C 1 ~C 4 4. The compound of formula (I) according to claim 1, wherein - is alkyl.

5. R 7 But hydrogen, C 1 ~C 4 - alkyl, or C 3 ~C 6 5. The compound of formula (I) according to any one of claims 1 to 4, wherein -cycloalkyl.

6. R 7 6. The compound of formula (I) according to claim 5, wherein is hydrogen or methyl.

7. B 1 is CR 10 and B 2 is CR 11 and R 10 and R 11 The compound of formula (I) according to any one of claims 1 to 6, wherein is independently selected from hydrogen, bromine, chlorine, or cyano.

8. W is O, N, *-CH 2 O- # , *-CH 2 NH- # , *-CH 2 S- # , or *-CH 2 - # In the formula, the star (*) indicates the position of the link to the carbonyl group, and # indicates Z 1 A compound of formula (I) according to any one of claims 1 to 7, wherein:

9. W is O, N, or *-CH 2 - # In the formula, the star (*) indicates the position of the link to the carbonyl group, and # indicates Z 1 9. A compound of formula (I) according to claim 8, wherein:

10. Z 1 But C 1 ~C 6 - alkyl, phenyl, or 6-membered heteroaryl, 1 ~C 6 - alkyl is unsubstituted or halogen, C 1 ~C 4 -Alkyl, C 1 ~C 4 -haloalkyl, phenyl, 5- to 6-membered heteroaryl, and C 3 ~C 6 -cycloalkyl; any of the 6-membered heteroaryl and the 5- to 6-membered heteroaryl contain 1 or 2 of the same or different heteroatoms selected from N or O, and any of the phenyl, the 6-membered heteroaryl and the 5- to 6-membered heteroaryl are unsubstituted or substituted with halogen, cyano, C 1 ~C 4 - alkyl, and C 3 ~C 6 -cycloalkyl. - substituted with one or two identical or different substituents selected from the group consisting of: - cycloalkyl;

11. Z 1 But C 1 ~C 6 -alkyl, phenyl, 2,4-difluorophenyl, 3,5-difluoro-2-furyl, 3-fluoro-2-furyl, 5-fluoro-2-furyl, 3,5-difluoro-2-thienyl, 3-fluoro-2-thienyl, 5-fluoro-2-thienyl, 2-fluorophenyl, 4-fluorophenyl, 3-fluoro-2-pyridyl, 5-fluoro-2-pyridyl, 3,4-difluoro-2-pyridyl, 3,5-difluoro-2-pyridyl, 4-fluoropyridazin-3-yl, 4,5-difluoropyridazin-3-yl, or 5-fluoropyridazin-4-yl; 1 ~C 6 10. Compounds of formula (I) according to any one of claims 1 to 9, wherein alkyl is unsubstituted or substituted with one or two identical or different substituents selected from the group consisting of chlorine, fluorine, bromine, methyl, ethyl, trifluoromethyl, difluoromethyl, cyclopropyl, cyclohexyl, phenyl, and 6-membered heteroaryl; said 6-membered heteroaryl contains one heteroatom selected from N; and said phenyl and said 6-membered heteroaryl are unsubstituted or substituted with one or two identical or different substituents selected from the group consisting of chlorine, bromine, fluorine, cyano, methyl, ethyl, and cyclopropyl.

12. An agrochemical composition comprising a fungicidally effective amount of a compound of formula (I) according to any one of claims 1 to 11.

13. 13. The agrochemical composition of claim 12, further comprising at least one additional active ingredient and / or an agrochemically acceptable diluent or carrier.

14. 12. A method for controlling or preventing infestation of useful plants by phytopathogenic microorganisms, which comprises applying to said plants, parts thereof or their habitat a fungicidally effective amount of a compound of formula (I) according to any one of claims 1 to 11, or a composition comprising said compound of formula (I).

15. Use of a compound of formula (I) according to any one of claims 1 to 11 as a fungicide.

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